Heterocyclic 1,3-diazepine-based thio­nes and selones as versatile halogen-bond acceptors

Utilizing the N-heterocyclic chalcogenones hexa­hydro-1,3-bis­(2,4,6-tri­methyl­phenyl)-2H-1,3-diazepine-2-thione (SDiazMesS) and hexa­hydro-1,3-bis­(2,4,6-tri­methyl­phenyl)-2H-1,3-diazepine-2-selone (SDiazMesSe) as halogen-bond acceptors, a total of 24 new cocrystals were prepared. The solid-state structures of the parent molecules were also determined, along with those of their aceto­nitrile solvates. Through the reaction of the chalcogen atom with molecular diiodine, a variety of S—I—I and Se—I—I fragments were formed, spanning a wide range of I—I bond orders. With acetone as a reaction solvent, molecular diiodine causes the oxidative addition of acetone to the chalcogen atom, resulting in new C—S, C—Se and C—C covalent bonds under mild conditions. The common halogen-bond donors, iodo­penta­fluoro­benzene, 1,2-, 1,3- and 1,4-di­iodo­tetra­fluoro­benzene, 1,3,5-tri­fluoro­tri­iodo­benzene and tetra­iodo­ethyl­ene resulted in halogen-bond-driven cocrystal formation. In most cases, the analogous SDiazMesS and SDiazMesSe cocrystals are isomorphic.

1. Introduction

Halogen bonding has long been known, and formally defined by the International Union of Pure and Applied Chemistry (IUPAC) in 2013, as an attractive interaction between an electrophilic region on a halogen atom (halogen-bond donor) and a nucleophilic region on another atom or molecule (halogen-bond acceptor) (Desiraju et al., 2013). The electrophilic region is referred to as the σ hole and is located at the `cap' on the halogen end of the covalent bond, and is accompanied by a `belt' of relatively higher electrostatic potential orthogonal to the bond (Murray et al., 2009; Politzer et al., 2010; Politzer & Murray, 2017). A similar electron density distribution is observed for the chalcogen atoms and is particularly pronounced for thio­nes and selones (Vogel et al., 2019). If the chalcogen atoms of these functional groups act as halogen-bond acceptors, the location of the higher electrostatic potential drives the halogen bond away from the terminus of the thione or selone double bond. Conversely, a chalcogen bond, an interaction analogous to a halogen bond involving the σ hole of a chalcogen atom, can occur at the terminus of the thione or selone double bond (Aakeroy et al., 2019).

As halogen-bond acceptor atoms, nitro­gen and oxygen have received considerably more attention than the heavier chalcogens. For example, a survey of the Cambridge Structural Database (CSD, Version 5.42, update 3; Groom et al., 2016), limited to organics, yields 918 results involving an N⋯I halogen bond (where the N⋯I distance is less than the sum of the van der Waals radii of the two atoms) to a pyridine-based nitro­gen atom. A similar search with urea-, thio­urea- or seleno­urea-based acceptors yields 36, 100 and 19 results, respectively. Amongst the limited published data involving Se⋯I interactions, the oxidative addition of interhalogens to diselones, resulting in I—Se—X hypervalent systems is notable (Juárez-Pérez et al., 2011). Our group has been particularly interested in the cooperation of halogen and chalcogen bonding as a versatile crystal engineering tool (Peloquin, McMillen et al., 2021a,b; Peloquin, McCollum et al., 2021; Peloquin, Alapati et al., 2021).

Motivated by the lack of published structural data involving halogen bonds to thio­ureas, and especially seleno­ureas, this work serves to further catalog the intermolecular interactions of these functionalities with common organoiodine compounds (Scheme 1 shows the organic halogen-bond acceptors and donors utilized in this study), as well as to investigate their reactivity and resulting halogen bonding with molecular diiodine.

To this end, the sterically encumbered diazepine chalcogenone derivatives hexa­hydro-1,3-bis­(2,4,6-tri­methyl­phenyl)-2H-1,3-diazepine-2-thione (SDiazMesS) and hexa­hydro-1,3-bis­(2,4,6-tri­methyl­phenyl)-2H-1,3-diazepine-2-selone (SDiazMesSe) were prepared, the latter of which has not yet been reported in the synthetic literature, and structurally characterized. These were subsequently utilized as halogen-bond acceptors, to explore their halogen bonding tendencies. Each of these parent molecules was reacted with molecular diiodine, which depending on reaction stoichiometry and solvent choice, provided a variety of C=S—I—I, C=Se—I—I and C=Se—I derivatives. When acetone was utilized as the reaction solvent with I₂, new S—C, Se—C and C—C bonds were formed via oxidation by I₂. Utilizing the six most common commercially available halogen bond donors, 1,2-di­iodo­tetra­fluoro­benzene (1,2-F₄DIB), 1,3-di­iodo­tetra­fluoro­benzene (1,3-F₄DIB), 1,4-di­iodo­tetra­fluoro­benzene (1,4-F₄DIB), 1,3,5-tri­fluoro­tri­iodo­benzene (1,3,5-F₃I₃B), iodo­penta­fluoro­benzene (IF₅B), and tetra­iodo­ethyl­ene (TIE), the molecular structures of 14 new cocrystals were determined. In most cases, the analogous SDiazMesS and SDiazMesSe cocrystals are isomorphic. No significant chalcogen⋯chalcogen (ch⋯ch) or chalcogen⋯iodine (ch⋯I) chalogen bonding or I⋯F halogen bonding is observed within this series of structures.

2. Experimental

2.1. Materials and instrumentation

All reactions were performed under aerobic conditions unless otherwise stated. Solvents were purified and degassed by standard procedures, and all commercially available reagents were used as received. The bis­(mesityl) formamidine MesN = CHNHMes (MesForm) was synthesized as reported (Kuhn & Grubbs, 2008) and its corresponding diazepinium bromide derivative (SDiazMesH)Br (Kolychev et al., 2009) was prepared by a modification of a literature procedure (Iglesias et al., 2008). ¹H and ¹³C NMR spectra were obtained on Jeol ECX-300 (300 MHz) or Jeol ECA-500 (500 MHz) FT spectrometers. Chemical shifts are reported in p.p.m. relative to SiMe₄ (δ = 0 p.p.m.) and were referenced internally with respect to the solvent resonances (¹H: δ 2.05 for d₅-acetone; ¹³C: δ 29.84 for (CD₃)₂CO; coupling constants are given in hertz (Hz). IR spectra were recorded on a PerkinElmer Spectrum 100 spectrometer using an attenuated total reflectance (ATR) accessory and are reported in cm⁻¹; relative intensities of the absorptions are indicated in parentheses (v = very strong, s = strong, m = medium, w = weak). Elemental analyses were determined by Atlantic Microlab, Inc. (Norcross, GA, USA).

For single-crystal X-ray analysis, crystals were mounted on low-background cryogenic loops using paratone oil. Data were collected at 100 K using Mo Kα radiation (λ = 0.71073 Å) on a Bruker D8 Venture diffractometer with an Incoatec Iµs microfocus source and a Photon 2 detector. Diffraction data were collected using φ and ω scans and subsequently processed and scaled using the APEX3 (SAINT/SADABS) (Bruker, 2017) software. The structures were solved with the SHELXT structure solution program and refined utilizing SHELXL, both incorporated in the OLEX2 (v1.5) program package (Sheldrick, 2015b,a; Dolomanov et al., 2009). Hydrogen atoms were placed in geometrically optimized positions using the appropriate riding models. In (SDiazMesS)·(MeCN), (SDiazMesSe)·(MeCN), (SDiazMesS)·(1,3-F₄DIB), (SDiazMesSe)·(1,3-F₄DIB), 2(SDiazMesS)·(1,3-F₄DIB), (SDiazMesS)·(1,3,5-F₃I₃B), 2(SDiazMesS)·(TIE) and 2(SDiazMesSe)·(TIE), positional disorder of the C—C—C—C portion of the diazepine ring and/or a mesityl substituent was modeled in two parts, utilizing the SIMU restraint as appropriate.

2.2. Preparation of SDiazMesS and SDiazMesSe

The bis­(mesityl)formamidine MesN = CHNHMes (MesForm) was synthesized as reported (Kuhn & Grubbs, 2008) and its corresponding diazepinium bromide derivative (SDiazMesH)Br, SDiazMesS and SDiazMesSe were prepared by a modification of literature procedures (Iglesias et al., 2008; Rais et al., 2016).

2.2.1. (SDiazMesH)Br

A stirred mixture of 1,4-di­bromo­butane (5.939 g, 27.506 mmol), the formamidine MesForm (7.000 g, 24.963 mmol), and potassium carbonate (1.989 g, 14.392 mmol) in aceto­nitrile (100 ml) was heated to reflux under argon for 24 h. The resulting solution was cooled to room temperature and concentrated under reduced pressure to ∼2 ml to give a very viscous tan-colored residue. Di­chloro­methane (25 ml) was added to the residue and the mixture stirred overnight, facilitating the separation of a fluffy, white precipitate. The resulting suspension was concentrated under reduced pressure to half volume, treated with cold di­ethyl ether (60 ml), and the sticky, peach-colored product was isolated by vacuum filtration and dried in vacuo for 24 h (7.820 g, 72%). ¹H NMR data (in CDCl₃): δ 2.27 (s, 6H, CH₃), 2.41 (s, 12H, CH₃), 2.56 (m, 4H, CH₂), 4.65 (m, 4H, CH₂), 6.94 (s, 4H, C₆H₂), 7.21 (s, 1H, NCHN); ¹H NMR data (in d₆-acetone): δ 2.28 (s, 6H, CH₃), 2.45 (s, 12H, CH₃), 2.55 (m, 4H, CH₂), 4.52 (m, 4H, CH₂), 7.05 (m, 4H, C₆H₂), 8.13 (s, 1H, NCHN).

2.2.2. SDiazMesS

A stirred mixture of (SDiazMesH)Br (5.106 g, 12.292 mmol), elemental sulfur (0.433 g, 13.506 mmol) and potassium carbonate (2.208 g, 15.976 mmol) in n-propanol (75 ml) was heated to reflux for 48 h. The resulting yellow suspension was concentrated to ∼2 ml under reduced pressure to give a beige viscous residue. The product was extracted into di­chloro­methane (50 ml) and the extract was treated with activated carbon (∼1 g) and filtered. The pale orange filtrate was washed with deionized water (3 × 30 ml), and the organic phase was dried over magnesium sulfate (∼1 g) and filtered. Concentration of the solution under vacuum to ∼1 ml and addition of hexanes (20 ml) led to the precipitation of the pale brown product, which was separated by filtration and dried in vacuo for 24 h (3.543 g, 79%). Mp = 179–181 °C (dec.). NMR data (in d₆-acetone): ¹H δ 2.09 (m, 4H, CH₂), 2.23 (s, 6H, CH₃), 2.29 (s, 12H, CH₃), 3.90 (m, 4H, CH₂), 6.85 (s, 6H, C₆H₂); ¹³C δ 19.0 (q, ¹J_C–H = 126, 4C, CH₃), 20.9 (q, ¹J_C–H = 128, 2C, CH₃), 26.4 (t, ¹J_C–H = 127, 2C, CH₂), 55.0 (t, ¹J_C–H = 138, 2C, NCH₂), 130.1 (d, ¹J_C–H = 164, 4C, C_m in C₆H₂), 135.5 (s, 4C, C_o in C₆H₂), 136.5 (s, 2C, C_p in C₆H₂), 145.5 (s, 2C, C_ipso in C₆H₂), C=S not observed. IR data: 3141 (w), 2939 (w), 2916 (m), 2854 (w), 2726 (w), 1679 (w), 1643 (s), 1607 (w), 1551 (w), 1488 (m), 1478 (m), 1465 (s), 1426 (m), 1381 (w), 1369 (m), 1359 (w), 1330 (w), 1308 (s), 1287 (vs), 1267 (m), 1214 (m), 1200 (w), 1182 (w), 1148 (w), 1121 (w), 1102 (w), 1032 (w), 1011 (w), 997 (w), 979 (w), 957 (w), 914 (w), 863 (w), 849 (s), 767 (m), 748 (w), 740 (w), 729 (w), 709 (w). Anal. Calc.: for C₂₃H₃₀N₂S: C, 75.4; H, 8.3; N, 7.6; found: C, 76.4; H, 8.2; N, 8.1%. Samples for single-crystal X-ray characterization were obtained from EtOH/DCM or MeCN.

2.2.3. SDiazMesSe

A stirred mixture of (SDiazMesH)Br (7.386 g, 17.779 mmol), gray selenium (1.862 g, 23.582 mmol), and potassium carbonate (3.2190 g, 23.291 mmol) in n-propanol (150 ml) was heated to reflux for 20 h. The resulting dark red-orange suspension was concentrated to ∼2 ml under reduced pressure to give a dark orange solid residue. The product was extracted into di­chloro­methane (30 ml) and the bright yellow-orange extract was washed with DI water (3 × 30 ml). The organic phase was separated, dried over magnesium sulfate (∼1 g), filtered, concentrated under vacuum to ∼1 ml, and treated with cold hexanes (10 ml), leading to the precipitation of flaky, orange-yellow product, which was isolated by vacuum filtration and dried in vacuo for 14 h (4.457 g, 61%). Mp = 188–190 °C (dec.). NMR data (in d₆-acetone): ¹H δ 2.15 (m, 4H, CH₂), 2.23 (s, 6H, CH₃), 2.30 (s, 12H, CH₃), 3.93 (m, 4H, CH₂), 6.86 (s, 6H, C₆H₂); ¹³C δ 19.1 (q, ¹J_C–H = 127, 4C, CH₃), 21.0 (q, ¹J_C–H = 127, 2C, CH₃), 25.7 (t, ¹J_C–H = 128, 2C, CH₂), 55.2 (t, ¹J_C–H = 139, 2C, NCH₂), 130.2 (d, ¹J_C–H = 164, 4C, C_m in C₆H₂), 135.3 (s, 4C, C_o in C₆H₂), 136.7 (s, 2C, C_p in C₆H₂), 146.6 (s, 2C, C_ipso in C₆H₂), 186.7 (s, 1C, C=Se). IR data: 2971 (w), 2945 (w), 2916 (w), 2854 (w), 1737 (m), 1676 (w), 1645 (s), 1607 (w), 1550 (w), 1489 (m), 1471 (s), 1430 (m), 1369 (m), 1360 (m), 1331 (m), 1286 (vs), 1275 (w), 1254 (w), 1215 (s), 1203 (w), 1185 (w), 1149 (w), 1121 (w), 1104 (w), 1032 (w), 1012 (w), 998 (w), 981 (w), 902 (w), 864 (w), 850 (s), 775 (w), 755 (w), 743 (w), 707 (w). Anal. Calc.: for C₂₃H₃₀N₂Se: C, 66.8; H, 7.3; N, 6.8; found: C, 66.7; H, 7.4; N, 6.7%. Samples for single-crystal X-ray characterization were obtained from EtOH/DCM or MeCN.

2.3. Reaction of SDiazMesS and SDiazMesSe with I₂

2.3.1. (SDiazMesS)I₂

Di­ethyl ether (10 ml) was added to a mixture of SDiazMesS (0.150 g, 0.409 mmol) and elemental iodine (0.104 g, 0.405 mmol), resulting in the formation, within minutes, of a dark-orange solid and a dark-red solution. After stirring the suspension for 17 h, the product was isolated by filtration and dried in vacuo for 24 h (0.154 g, 61%). Mp = 141–143 °C (dec.). NMR data (in d₆-acetone): ¹H δ 2.27 (s, 10 H, CH₃ + CH₂), 2.37 (s, 12H, CH₃), 4.12 (s, 4H, CH₂) 6.96 (s, 4H, C₆H₂); ¹³C δ 18.5 (q, ¹J_C–H = 127, 4C, CH₃), 20.5 (q, ¹J_C–H = 128, 2C, CH₃), 23.7 (t, ¹J_C–H = 130, 2C, CH₂), 54.7 (t, ¹J_C–H = 143, 2C, CH₂), 129.6 (d, ¹J_C–H = 157, 4C, C_m in C₆H₂), 133.7 (d, ²J_C–H = 6, 4C, C_o in C₆H₂), 136.7 (s, 2C, C_p in C₆H₂), 142.6 (s, 2C, C_ipso in C₆H₂), 176.3 (s, 1C, C=S). IR data: 2948 (w), 2910 (w), 2868 (w), 2730 (w), 1608 (w), 1506 (s), 1474 (m), 1452 (w), 1432 (m), 1391 (m), 1373 (w), 1365 (w), 1354 (w), 1337 (m), 1306 (s), 1286 (vs), 1270 (vs), 1211 (w), 1202 (w), 1187 (w), 1153 (w), 1105 (w), 1036 (w), 1014 (w), 999 (w), 978 (w), 966 (w), 937 (w), 926 (w), 910 (w), 892 (w), 853 (s), 841 (m), 798 (w), 756 (m), 745 (w), 729 (w), 706 (w). Anal. Calc.: for C₂₃H₃₀I₂N₂S: C, 44.5; H, 4.9; N, 4.5; found: C, 44.3; H, 4.9; N, 4.5%. Crystals suitable for X-ray diffraction analysis were obtained through the slow evaporation of an ethano­lic solution of the compound.

2.3.2. (SDiazMesSe)I₂

A mixture of SDiazMesSe (0.144 g, 0.349 mmol) and elemental iodine (0.093 g, 0.366 mmol) in di­ethyl ether (10 ml) was stirred overnight at room temperature. The resulting reddish-brown suspension was concentrated under reduced pressure to ∼1 ml, treated with di­ethyl ether (5 ml), and the dark orange product was isolated by filtration, washed with di­ethyl ether (2 ml), and dried in vacuo for 18 h (0.210 g, 91%). Mp = 195–198 °C (dec.). ¹H NMR data (in d₆-acetone): δ 2.28 (s, 3H, CH₃), 2.33 (s, 4H, CH₂), 2.37 (s, 6H, CH₃), 4.22 (s, 4H, CH₂), 6.98 (s, 2H, C₆H₂); ¹³C NMR data (in d₆-DMSO): δ 17.9 (q, ¹J_C–H = 128, 4C, CH₃), 20.0 (q, ¹J_C–H = 127, 2C, CH₂), 22.6 (t, ¹J_C–H = 131, 2C, CH₂), 55.5 (t, ¹J_C–H = 146, 2C, CH₂), 129.5 (d, ¹J_C–H = 158, 2C, C_m in C₆H₂), 133.4 (s, ¹J_C–H = 160, 4C, C_o in C₆H₂), 138.1 (s, 4C, C_p in C₆H₂), 142.2 (s, 2C, C_ipso in C₆H₃), C=Se not observed. IR data: 2950 (m), 2911 (m), 2854 (w), 2730 (w), 1777 (w), 1739 (w), 1607 (m), 1516 (s), 1474 (s), 1452 (w), 1434 (s), 1392 (m), 1374 (m), 1365 (m), 1355 (w), 1338 (m), 1308 (w), 1293 (vs), 1282 (vs), 1269 (vs), 1261 (vs), 1210 (m), 1189 (m), 1150 (w), 1104 (m), 1035 (m), 998 (m), 979 (w), 957 (w), 938 (w), 923 (w), 896 (w), 853 (s), 739 (m), 704 (w). Anal. Calc.: for C₂₃H₃₀I₂N₂Se: C, 41.4; H, 4.5; N, 4.2; found: C, 41.1; H, 4.7; N, 4.1%. Crystals suitable for X-ray diffraction analysis were obtained through the slow evaporation of an ethano­lic solution of the compound.

2.4. Preparation of cocrystals

2.4.1. (SDiazMesS)·(1,2-F₄DIB)

In a 20 ml glass vial, SDiazMesS (30 mg, 0.082 mmol) and 1,2-F₄DIB (33 mg, 0.082 mmol) were dissolved in a 1:1 mixture of ethanol and di­chloro­methane (5 ml) with gentle heating. The solvent was allowed to slowly evaporate under ambient conditions (18–20 °C) until colorless, needle-like crystals were observed.

2.4.2. (SDiazMesS)·(1,3-F₄DIB)

Using the same procedure as for (SDiazMesS)·(1,2-F₄DIB), SDiazMesS (30 mg, 0.082 mmol) and 1,3-F₄DIB (66 mg, 0.16 mmol) were combined to yield colorless, plate-like crystals.

2.4.3. (SDiazMesSe)·(1,3-F₄DIB)

Using the same procedure as for (SDiazMesS)·(1,2-F₄DIB), SDiazMesSe (30 mg, 0.073 mmol) and 1,3-F₄DIB (58 mg, 0.15 mmol) were combined to yield yellow, needle-like crystals.

2.4.4. 2(SDiazMesS)·(1,3-F₄DIB)

Using the same procedure as for (SDiazMesS)·(1,2-F₄DIB), SDiazMesS (60 mg, 0.16 mmol) and 1,3-F₄DIB (33 mg, 0.082 mmol) were combined to yield colorless, needle-like crystals.

2.4.5. 2(SDiazMesSe)·(1,3-F₄DIB)

Using the same procedure as for (SDiazMesS)·(1,2-F₄DIB), SDiazMesSe (60 mg, 0.15 mmol) and 1,3-F₄DIB (29 mg, 0.073 mmol) were combined to yield colorless, needle-like crystals.

2.4.6. 2(SDiazMesS)·(1,4-F₄DIB)^t and 2(SDiazMesS)·(1,4-F₄DIB)^m

Using the same procedure as (SDiazMesS)·(1,2-F₄DIB), SDiazMesS (60 mg, 0.16 mmol) and 1,4-F₄DIB (33 mg, 0.082 mmol) were combined to yield 2(SDiazMesS)·(1,4-F₄DIB)^t as colorless, needle-like crystals on the sides of the vial and 2(SDiazMesS)·(1,4-F₄DIB)^m as colorless, plank-like crystals from the bottom surface of the vial.

2.4.7. 2(SDiazMesSe)·(1,4-F₄DIB)^t

Using the same procedure as (SDiazMesS)·(1,2-F₄DIB), SDiazMesSe (60 mg, 0.15 mmol) and 1,4-F₄DIB (29 mg, 0.073 mmol) were combined to yield colorless, plank-like crystals.

2.4.8. (SDiazMesS)·(1,3,5-F₃I₃B)

Using the same procedure as (SDiazMesS)·(1,2-F₄DIB), SDiazMesS (30 mg, 0.082 mmol) and 1,3,5-F₃I₃B (42 mg, 0.082 mmol) were combined to yield colorless, needle-like crystals.

2.4.9. (SDiazMesSe)·(1,3,5-F₃I₃B)

Using the same procedure as (SDiazMesS)·(1,2-F₄DIB), SDiazMesSe (30 mg, 0.073 mmol) and 1,3,5-F₃I₃B (37 mg, 0.073 mmol) were combined to yield yellow, needle-like crystals.

2.4.10. (SDiazMesS)·(IF₅B)

Using the same procedure as (SDiazMesS)·(1,2-F₄DIB), SDiazMesS (30 mg, 0.082 mmol) and IF₅B (120 mg, 0.41 mmol) were combined to yield colorless, plate-like crystals.

2.4.11. 2(SDiazMesSe)·5(IF₅B)

In a 1 ml glass tube, SDiazMesSe (30 mg, 0.073 mmol) was dissolved in IF₅B (0.25 ml, 1.8 mmol). The solvent was allowed to slowly evaporate under ambient conditions, yielding yellow, plate-like crystals after approximately one week.

2.4.12. 2(SDiazMesS)·(TIE)

Using the same procedure as for (SDiazMesS)·(1,2-F₄DIB), SDiazMesS (60 mg, 0.16 mmol) and TIE (44 mg, 0.082 mmol) were combined to yield yellow, plate-like crystals.

2.4.13. 2(SDiazMesSe)·(TIE)

Using the same procedure as for (SDiazMesS)·(1,2-F₄DIB), SDiazMesSe (60 mg, 0.15 mmol) and TIE (39 mg, 0.073 mmol) were combined to yield yellow, block-like crystals.

3. Results and discussion

3.1. Synthesis of SDiazMesS and SDiazMesSe

The N-heterocyclic chalcogenones SDiazMesE (E = S, Se), envisioned to have good solubility in common organic solvents and exhibit simple ¹H and ¹³C NMR spectra to facilitate characterization of products, were synthesized in three steps (Scheme 2).

.

Commercially available 2,4,6-tri­methyl­aniline (mesityl­amine) was reacted neat with tri­ethyl­orthoformate in the presence of a catalytic amount of acetic acid (Kuhn & Grubbs, 2008) to produce the bis­(mesityl)formamidine MesN=CHNHMes (MesForm) in ∼80% yield. The formamidine was then reacted with 1,4-di­bromo­butane and potassium carbonate in refluxing aceto­nitrile (Iglesias et al., 2008) to generate the diazepinium bromide derivative (SDiazMesH)Br, which was isolated in ∼70% yield. Finally, the diazepinium salt is reacted with either elemental sulfur or gray selenium in the presence of a base (K₂CO₃) in refluxing n-propanol to form the desired thione and selone products in 60–80% yield. The two chalcogenones were fully characterized by a combination of analytical and spectroscopic techniques, including elemental analysis, IR, and ¹H and ¹³C NMR spectroscopies, and single-crystal X-ray diffraction, as described in the next section.

3.2. Structure of SDiazMesS and SDiazMesSe and their MeCN solvates

The parent compound SDiazMesS crystallizes in the monoclinic space group P2₁/c, whereas SDiazMesSe crystallizes in the orthorhombic space group Pbca (Fig. 1). The thio­urea and seleno­urea are prominent in the respective structures, with a C=S length of 1.6887 (13) Å and an average C=Se length of 1.850 (4) Å from the two unique molecules in the asymmetric unit (Table 1). Despite the cyclic nature of the molecule's core, the N—C=E (E = S, Se) angle remains at approximately 120°, consistent with that of an isolated thio­urea or seleno­urea molecule (Tomkowiak & Katrusiak, 2018). In SDiazMesS, weak C—H⋯S hydrogen bonds [C⋯S = 3.7030 (15) Å and 3.4858 (14) Å], involving hydrogen atoms of the heterocyclic ring, contribute to the stacking of molecules along the c axis. With two unique molecules in the asymmetric unit of SDiazMesSe, the hydrogen-bonding pattern is more complex. To one selenium atom, weak C—H⋯Se hydrogen bonds [C⋯Se = 3.671 (2) Å and 3.665 (2) Å] are observed to two different molecules, both involving hydrogen atoms of the heterocyclic rings. In both cases, the mesityl rings are nearly perpendicular to the urea plane. For example, in SDiazMesS, the mesityl-to-urea plane angles are 91.46 (4)° and 89.60 (4)°. These geometric parameters remain consistent throughout the variety of cocrystals, adducts, and solvates in this study. Unlike the unsolvated structures of the parent molecules, the aceto­nitrile solvates (SDiazMesS)·(MeCN) and (SDiazMesSe)·(MeCN) are isomorphous, with a weak hydrogen bonding interaction observed between the chalcogen atom and the aceto­nitrile molecule.

Table 1
Selected bond lengths (Å) in SDiazMesE, (SDiazMesE)·(MeCN) (E = S, Se) and the products of reaction with I₂

Compound	dC=E	dC—N		E—I	I—I
SDiazMesS	1.6887 (13)	1.3625 (16)	1.361 (2)	–	–
SDiazMesSe	1.851 (2)	1.361 (3)	1.348 (3)	–	–
	1.850 (2)	1.356 (3)	1.353 (3)	–	–
(SDiazMesS)·(MeCN)	1.6821 (15)	1.3627 (17)	1.3689 (15)	–	–
(SDiazMesSe)·(MeCN)	1.8498 (18)	1.355 (2)	1.3586 (19)	–	–
SDiazMesS—I2	1.738 (3)	1.356 (4)	1.337 (5)	2.6738 (9)	2.8794 (4)
SDiazMesSe—I2	1.8973 (16)	1.334 (3)	1.351 (2)	2.7559 (4)	2.9106 (4)
(SDiazMesS—I2)·(I2)	1.7555 (18)	1.335 (3)	1.344 (2)	2.5052 (5)	3.0803 (4)
[(SDiazMesSe—I)(I3)]	1.921 (10)	1.338 (13)	1.339 (13)	2.5807 (14)	3.2052 (10)
[(SDiazMesSe—I)(I3)]·(DCM)	1.9274 (17)	1.331 (3)	1.338 (3)	2.5958 (3)	3.1867 (3)
[(SDiazMesSe-DMK)(I3)]·(I2)	1.910 (9)	1.320 (12)	1.336 (11)	–	–
[(SDiazMesS-MIBK)(I3)]	1.772 (4)	1.339 (4)	1.329 (4)	–	–
[(SDiazMesSe-MIBK)(I3)]	1.9284 (17)	1.340 (3)	1.328 (2)	–	–

Figure 1 Views of the molecular structures of SDiazMesS (left-hand view) and SDiazMesSe (right-hand view). Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

3.3. Reaction of SDiazMesS and SDiazMesSe with I₂

The reaction of molecular iodine with SDiazMesS and SDiazMesSe provided a rich series of products depending on the ratio of I₂ to thione or selone and the solvent choice (Scheme 3).

The reaction of SDiazMesS or SDiazMesSe with a stoichiometric amount of I₂ in di­ethyl ether provides SDiazMesS-I₂ or SDiazMesSe-I₂, both crystallizing in the triclinic space group . In both cases, short chalcogen⋯iodine distances are observed [S—I = 2.6738 (9) Å and Se—I = 2.7559 (4) Å], with concomitant lengthening of the I—I bond to 2.8794 (4) Å in SDiazMesS-I₂ and 2.9106 (4) Å in SDiazMesSe-I₂. These I—I distances correspond to bond orders of 0.59 and 0.53, respectively, as calculated using the expression of Pauling, D(n′) = D(1) − 0.71 log (n′) with a D(1) of 2.72 Å (Pauling, 1960). A series of weak C—H⋯I hydrogen bonds consolidate the packing.

The reaction with 2.5 molar equivalents of I₂ in a 1:1 mixture of ethanol and di­chloro­methane provides different products from SDiazMesS and SDiazMesSe. When the reaction was conducted with SDiazMesS, the cocrystal (SDiazMesS—I₂)·(I₂) was obtained in the triclinic space group . The bond distances within the S—I—I fragment are reduced from those in SDiazMesS, with the S—I distance shrinking to 2.5052 (5) Å while the I–I distance further elongates to 3.0803 (4) Å. This change in bond geometries is indicative of further progression towards the dipolar I⁺⋯I⁻ extreme, with a calculated bond order of 0.31. The consolidation of the negative charge on the terminal iodine atom of the S—I—I fragment contributes to its increased ability to serve as a halogen-bond acceptor. The incorporation of a diiodine molecule within the structure aids in the formation of chains in the direction through I⋯I halogen bonding. There are two such unique I⋯I halogen bonds formed at each terminal iodine atom of the S—I—I, both of which are similar in length [I⋯I = 3.4171 (4) Å and 3.4694 (5) Å]. In contrast to the reaction of SDiazMesS with excess I₂, the reaction of 2.5 molar equivalents of I₂ with SDiazMesSe in 1:1 ethanol:dichloromethane provides the salt [(SDiazMesSe—I)(I₃)]. Crystalline [(SDiazMesSe—I)(I₃)] forms within five minutes, and if this material is recrystallized from di­chloro­methane, the crystalline solvate [(SDiazMesSe—I)(I₃)]·(DCM) is obtained. In both cases, the Se—I—I fragment is better represented as (Se—I⁺)(I₃⁻). This assignment is supported by the further contraction of the Se–I distance to 2.5807 (14) Å and expansion of the I⁺⋯I distance to 3.2052 (10) Å relative to SDiazMesSe—I₂. This I⋯I distance would correspond to a calculated bond order of only 0.20. The C=Se length remains relatively unchanged [1.921 (10) Å] compared to SDiazMesSe—I₂ (1.8973 (16) Å. The triiodide anion in both salts is asymmetric, with the two I—I lengths of 3.0222 (10) Å and 2.8492 (10) Å in [(SDiazMesSe—I)(I₃)] and 3.0098 (6) Å and 2.8426 (6) Å in [(SDiazMesSe—I)(I₃)]·(DCM). This degree of asymmetry is in line with other reported triiodide salts (Kobra et al., 2018). In [(SDiazMesSe—I)(I₃)], halogen bonding does not contribute to the long-range packing motif, beyond the aforementioned connection of one end of I₃⁻ to the Se—I fragment; however, in [(SDiazMesSe—I)(I₃)]·(DCM), a combination of I⋯I halogen bonding and Se⋯I chalcogen bonding contributes to the formation of chains along the a axis (Fig. 2).

Figure 2 Views of the molecular structures of the products of the reaction of I2 with SDiazMesS and SDiazMesSe in non-acetone solvents. Intermolecular I⋯I and Se⋯I interactions are indicated by magenta and black dotted lines, respectively. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

The use of acetone as the reaction solvent allowed access to new organic products resulting from forming a new covalent bond between the chalcogen atom and a methyl carbon of acetone (Fig. 3). When the reaction of SDiazMesSe and 2.5 molar equivalents of diiodine was conducted in acetone, the salt [(SDiazMesSe-DMK)(I₃)]·(I₂) was obtained, displaying an added di­methyl­ketone (DMK) fragment, resulting from the diiodine-promoted addition of an acetone molecule to the selenium atom. The slight elongation of the C=Se bond and negligible change in the C—N lengths suggest the positive charge is primarily localized to the selenium atom (Table 1). If a 1:1 mixture of ethanol and acetone was utilized as the reaction solvent for the reaction with 2.5 molar equivalents of I₂, the isomorphic products [(SDiazMesS-MIBK)(I₃)] and [(SDiazMesSe-MIBK)(I₃)] were obtained, both crystallizing in the triclinic space group . The methyl­iso­butyl­ketone (MIBK) fragment bound to the chalcogen atom results from the further bond formation of the methyl carbon of [(SDiazMesSe-DMK)(I₃)]·(I₂) with the carbonyl carbon of an additional acetone molecule along with de­oxy­genation. A related reaction involving the addition of acetone to a sulfur atom in 1,4-di­thiane has been previously reported (Peloquin, Alapati et al., 2021). Just as in [(SDiazMesSe-DMK)(I₃)]·(I₂), the only slight lengthening of C—S and C—Se distances, along with a negligible change in C—N distances, relative to the parent molecule indicate the positive charge is primarily localized on the chalcogen atom. The triiodide anion is pinned in place by weak type I halogen bonds with the I₂ molecule. While all attempts to isolate the analogous SDiazMesS-containing structure to [(SDiazMesSe-DMK)(I₃)]·(I₂) were unsuccessful, the isolation of [(SDiazMesS-MIBK)(I₃)] does suggest its formation occurs. Adding ethanol to the reaction mixture reduces the overall solvent polarity and likely supports the solubility of the increased aliphatic character of the MIBK fragment over DMK.

Figure 3 Views of the molecular structures of the products of the reaction of I2 with SDiazMesS and SDiazMesSe in acetone. Intermolecular I⋯I interactions are indicated by magenta dotted lines. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

3.4. Cocrystallization of SDiazMesS and SDiazMesSe with iodo­fluoro­benzenes

The cocrystal (SDiazMesS)·(1,2-F₄DIB) crystallizes in the orthorhombic space group Pna2₁ with one molecule each of SDiazMesS and 1,2-F₄DIB within the asymmetric unit (Fig. 4). C—I⋯S halogen bonding occurs between the thione sulfur atom and only one iodine atom of 1,2-F₄DIB, leading to the formation of discrete halogen bonded dimers. The halogen-bond distance in this cocrystal, 3.2092 (12) Å, is significantly shorter than measured in the ternary cocrystal of thio­urea, 1,2-F4DIB, and 18-crown-6 [3.4680 (6) Å] (Topić & Rissanen, 2016). The lack of I⋯S halogen bonding to the second iodine atom is likely due to a combination of the steric bulk of SDiazMesS and the proximity of the iodine atoms in 1,2-F₄DIB. Neighboring dimers consolidate through a combination of weak C—H⋯I and C—H⋯S interactions. All attempts to isolate the corresponding SDiazMesSe cocrystal were unsuccessful.

Figure 4 Halogen bonding in (SDiazMesS)·(1,2-F4DIB). Intermolecular I⋯S halogen bonding is indicated by a magenta dotted line. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

With 1,3-F₄DIB as the halogen bond donor, four cocrystalline structures were obtained (Fig. 5). The first two, (SDiazMesS)·(1,3-F₄DIB) and (SDiazMesSe)·(1,3-F₄DIB), are isomorphic. Both cocrsytals are obtained in the ortho­rhombic space group P2₁2₁2₁ with one molecule of either SDiazMesS or SDiazMesSe along with one molecule of 1,3-F₄DIB. A pair of nearly identical length C—I⋯S halogen bonds connect SDiazMesS or SDiazMesSe molecules with molecules of 1,3-F₄DIB in alternating fashion to form helical chains propagating along the b axis. The packing is consolidated along the a axis by weak C—H⋯π interactions and in the c direction by C—H⋯F interactions, both involving hydrogen atoms of the heterocyclic ring. The addition of a second equivalent of SDiazMesS or SDiazMesSe results in the cocrystals 2(SDiazMesS)·(1,3-F₄DIB) and 2(SDiazMesSe)·­(1,3-F₄DIB). Just as in the 1:1 cocrystals, the 2:1 cocrystals are isomorphic with one another, crystallizing in the monoclinic space group C2/c. Discrete halogen bonding units are formed with only one halogen bond observed at each chalcogen atom. These units stack along the c axis through π⋯π stacking of the 1,3-F₄DIB rings, with ring plane-to-ring plane distances of 3.2840 (10) Å and 3.3046 (12) Å and slippage of 2.359 Å and 2.337 Å in 2(SDiazMesS)·(1,3-F₄DIB) and 2(SDiazMesSe)·(1,3-F₄DIB) respectively. These four cocrystals represent the first reported examples of halogen-bonded cocrystals of 1,3-F₄DIB with a thio­urea or seleno­urea molecule.

Figure 5 Halogen bonding in the 1,3-F4DIB-containing cocrystals. Intermolecular I⋯S and I⋯Se halogen bonding is indicated by magenta dotted lines. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

The reaction with the common halogen bond donor 1,4-F₄DIB yielded two polymorphic structures with SDiazMesS: 2(SDiazMesS)·(1,4-F₄DIB)^t, which crystallized in the triclinic space group , and 2(SDiazMesS)·(1,4-F₄DIB)^m which crystallized in the monoclinic space group P2₁/c. The triclinic isomorph, 2(SDiazMesSe)·(1,4-F₄DIB)^t, was obtained with SDiazMesSe (Fig. 6). All attempts to isolate the monoclinic isomorph with SDiazMesSe were unsuccessful. In all three cases, a single halogen bond is observed at each chalcogen atom, forming discrete units from two thione or selone molecules and one molecule of 1,4-F₄DIB. For the triclinic isomorphs, the halogen-bond geometry is nearly linear, with a C—I⋯S angle of 175.67 (9)° in 2(SDiazMesS)·(1,4-F₄DIB)^t and a C—I⋯Se angle of 173.97 (4)° in 2(SDiazMesSe)·(1,4-F₄DIB)^t. The iodine⋯chalcogen distances in these triclinic polymorphs [I⋯S = 3.2318 (7) Å and I⋯Se = 3.2553 (3) Å] are shorter than the analogous cocrystals with thio­urea [I⋯S = 3.287 (12) Å] or seleno­urea [I⋯Se = 3.3151 (17) Å] (Arman et al., 2010; Chernysheva & Haukka, 2021). Weak chalcogen⋯hydrogen interactions contribute to the stacking of these discrete units along the a axis. In the monoclinic polymorph, while the discrete 2:1 halogen bonding units are maintained, the C—I⋯S halogen bond is elongated relative to the triclinic polymorph, and deviates significantly from linearity [143.57 (6)°]. This geometric arrangement may suggest an intermediate between true halogen and chalcogen bonds. The (C—)I iodine atom is also involved in a weak I⋯π interaction [3.646 (2) Å]. The repositioning of the 1,4-F₄DIB between the two SDiazMesS molecules in the monoclinic polymorph compared to the triclinic polymorph enable the iodine atoms to be involved in weak I⋯π interactions [3.646 (2) Å].

Figure 6 Halogen bonding in the 1,4-F4DIB-containing cocrystals. Intermolecular I⋯S and I⋯Se halogen bonding is indicated by magenta dotted lines. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

While the di­iodo­tetra­fluoro­benzene-containing cocrystal systems discussed thus far show roughly equivalent behavior between sulfur and selenium, the 1,3,5-F₃I₃B cocrystals (SDiazMesS)·(1,3,5-F₃I₃B) and (SDiazMesSe)·(1,3,5-F₃I₃B) do display a subtle, but important difference (Fig. 7). In this pair, the structures are not isomorphic, with (SDiazMesS)·(1,3,5-F₃I₃B) crystallizing in the monoclinic space group P2₁/c and (SDiazMesSe)·(1,3,5-F₃I₃B) in space group P2₁/n. In both cases, a pair of iodine⋯chalcogen halogen bonds are observed at each chalcogen atom. Each of these interactions ranges in normalized distance parameter, R_XB, from 0.85 to 0.92. The third iodine atom of each 1,3,5-F₃I₃B molecule drives the differences in the overall packing motif. Of the three symmetry unique 1,3,5-F₃I₃B molecules in (SDiazMesS)·(1,3,5-F₃I₃B), the third iodine atom of two of these (I2 and I8) have the appropriate geometric orientation to participate in a C—I⋯S halogen bond [C—I⋯S = 170.5 (2)° and 177.9 (2)°], but the iodine⋯sulfur distance is well beyond the sum of the van der Waals radii (R_XB = 1.12 and 1.14). This series of interactions contributes to the formation of ring-link units consisting of six SDiazMesS and six 1,3,5-F₃I₃B molecules. The third iodine atom of the final symmetry unique 1,3,5-F₃I₃B molecule participates in a weak type I, I⋯I interaction. In (SDiazMesSe)·(1,3,5-F₃I₃B), two primary C—I⋯Se halogen bonds (R_XB = 0.90 and 0.92) again occur at each selenium atom. However, the third iodine atom of each 1,3,5-F₃I₃B molecule drives a difference in the overall packing motif. In this case, a weak C—I⋯Se halogen bond occurs roughly at the sum of the van der Waals radii (R_XB = 1.01). This weak contact, probably enabled by the increased van der Waals radius of selenium over sulfur, and therefore decreased steric congestion around the chalcogen atom, is enough to consolidate the halogen bonding motif into a ladder-like chain propagating in the c direction. These two cocrystals represent the first reported examples of halogen-bonded cocrystals of 1,3,5-F₃I₃B with a thio­urea or seleno­urea.

Figure 7 Halogen bonding in the 1,3,5-F3I3B-containing cocrystals. Intermolecular I⋯S and I⋯Se halogen bonding is indicated by magenta dotted lines. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

With the halogen bond donor iodo­penta­fluoro­benzene (IF₅B), different reaction conditions were required for SDiazMesS and SDiazMesSe, resulting in dramatically different cocrystalline structures (Fig. 8). By reacting five equivalents of IF₅B with SDiazMesS in ethanol, (SDiazMesS)·(IF₅B) was obtained in the orthorhombic space group Pna2₁. A single I⋯S halogen bond is observed at each sulfur atom. The halogen bond length [I⋯S = 3.1809 (14) Å] is comparable to that measured in the ternary cocrystal of IF₅B, thio­urea, and 18-crown-6 [I⋯S = 3.1977 (14) Å] (Topić & Rissanen, 2016). These halogen bonded pairs stack along the a axis through π⋯π stacking of the IF₅B molecules, with a centroid to centroid distance between rings of 3.0340 (19) Å and slippage of 2.925 Å. The reaction conditions which produced (SDiazMesS)·(IF₅B) did not yield the analogous cocrystal with SDiazMesSe. To force cocrystallization, SDiazMesSe was dissolved in neat IF₅B, resulting in the cocrystal 2(SDiazMesSe)·5(IF₅B). This cocrystal was obtained in the monoclinic space group P2₁/c. In contrast to (SDiazMesS)·(IF₅B), in which only one halogen bond is observed to each chalcogen atom, two I⋯Se halogen bonds are observed to each selenium atom in 2(SDiazMesSe)·5(IF₅B). The length of these halogen bonds [I⋯Se = 3.2808 (5) Å and 3.3211 (7) Å] are comparable to the analogous distance in the reported cocrystal of IF₅B and 1,1-di­methyl­seleno­urea [I⋯Se = 3.2841 (12) Å] (Chernysheva et al., 2021). The halogen bonds are similar when normalized for the increased van der Waals radius of selenium versus sulfur. The packing is consolidated along the a axis through weak C—F⋯π interactions.

Figure 8 Halogen bonding in (SDiazMesS)·(IF5B) and 2(SDiazMesSe)·5(IF5B). Intermolecular I⋯S and I⋯Se halogen bonding is indicated by magenta dotted lines. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

3.5. Cocrystallization of SDiazMesS and SDiazMesSe with tetra­iodo­ethyl­ene

The final pair of cocrystals, 2(SDiazMesS)·(TIE) and 2(SDiazMesSe)·(TIE), are both obtained in the triclinic space group , with one thione or selone molecule and one half of a TIE molecule per asymmetric unit. A single halogen bond is observed to the chalcogen atom, contributing to discrete 2:1 units within the structure (Fig. 9). The remaining two iodine atoms of each TIE molecule appear to be pinned in place by weak C—H⋯I interactions from methyl groups of three neighboring SDiazMesE molecules, contributing to the formation of ribbons in the bc plane.

Figure 9 Halogen bonding in the TIE-containing cocrystals. Intermolecular I⋯S and I⋯Se halogen bonding is indicated by magenta dotted lines. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

4. Conclusions

The heterocyclic molecules hexa­hydro-1,3-bis­(2,4,6-tri­methyl­phenyl)-2H-1,3-diazepine-2-thione and hexa­hydro-1,3-bis­(2,4,6-tri­methyl­phenyl)-2H-1,3-diazepine-2-selone provided a robust template for halogen and/or chalcogen bonding interactions, yielding a total of 24 new cocrystal structures. The reaction with molecule diiodine provided products incorporating S—I—I and Se—I—I fragments with a wide range of bond orders. When this reaction was conducted in acetone, oxidative addition of acetone to the chalcogen atom allowed the formation of new C—S, C—Se and C—C covalent bonds under mild conditions. Cocrystallization with iodo­penta­fluoro­benzene, 1,2-, 1,3- and 1,4-di­iodo­tetra­fluoro­benzene, 1,3,5-tri­fluoro­tri­iodo­benzene, and tetra­iodo­ethyl­ene reveals structures that, in most cases, show a preference for halogen over chalcogen bonding and are typically isomorphic. This series of structural data supports the power of crystallographic study to reveal unexpected and unique interactions and reaction pathways.

Supporting information

Computing details

For all structures, data collection: APEX3 v2017.3-0 (Bruker AXS Inc., 2017); cell refinement: SAINT V8.38A (Bruker AXS Inc., 2017); data reduction: SAINT V8.38A (Bruker AXS Inc., 2017); program(s) used to solve structure: SHELXT 2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL 2018/3 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Olex2 1.5 (Dolomanov et al., 2009).

(SDiazMesS)

Crystal data

C23H30N2S	F(000) = 792
Mr = 366.55	Dx = 1.186 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.4064 (14) Å	Cell parameters from 9938 reflections
b = 8.7386 (9) Å	θ = 2.6–27.9°
c = 14.8229 (14) Å	µ = 0.17 mm^−1
β = 104.983 (3)°	T = 100 K
V = 2052.9 (3) Å^3	Block, colourless
Z = 4	0.30 × 0.19 × 0.17 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	3717 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.044
φ and ω scans	θmax = 26.5°, θmin = 2.6°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −20→19
Tmin = 0.706, Tmax = 0.746	k = −10→10
33473 measured reflections	l = −18→18
4240 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0371P)^2 + 1.5577P] where P = (Fo^2 + 2Fc^2)/3
4240 reflections	(Δ/σ)max = 0.001
241 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.69533 (2)	0.74837 (4)	0.29532 (2)	0.01726 (10)
N1	0.80101 (7)	0.72854 (13)	0.46402 (8)	0.0151 (2)
C1	0.71991 (8)	0.75052 (14)	0.41320 (9)	0.0139 (3)
C2	0.82151 (9)	0.67659 (17)	0.56223 (9)	0.0190 (3)
H2A	0.875834	0.620679	0.576717	0.023*
H2B	0.777332	0.604724	0.570419	0.023*
N2	0.65924 (7)	0.77220 (13)	0.45957 (8)	0.0149 (2)
C3	0.82787 (9)	0.80908 (19)	0.63033 (10)	0.0226 (3)
H3A	0.879540	0.869083	0.632559	0.027*
H3B	0.831765	0.768877	0.693744	0.027*
C4	0.75048 (9)	0.91216 (17)	0.59967 (10)	0.0210 (3)
H4A	0.743420	0.971097	0.654188	0.025*
H4B	0.759687	0.986048	0.552646	0.025*
C5	0.67010 (9)	0.82163 (17)	0.55817 (9)	0.0184 (3)
H5A	0.669915	0.729642	0.597099	0.022*
H5B	0.621009	0.885205	0.561472	0.022*
C7	0.89749 (8)	0.57991 (16)	0.39698 (9)	0.0170 (3)
C6	0.86912 (8)	0.72241 (16)	0.41884 (9)	0.0157 (3)
C9	1.00943 (9)	0.70720 (19)	0.34508 (10)	0.0213 (3)
C8	0.96802 (9)	0.57501 (17)	0.36037 (9)	0.0196 (3)
H8	0.988079	0.478646	0.345599	0.024*
C10	0.97800 (9)	0.84722 (17)	0.36537 (10)	0.0201 (3)
H10	1.004896	0.938571	0.353551	0.024*
C11	0.90822 (9)	0.85794 (16)	0.40253 (9)	0.0175 (3)
C12	0.85341 (9)	0.43400 (17)	0.41083 (11)	0.0228 (3)
H12A	0.876495	0.396782	0.474710	0.034*
H12B	0.862168	0.356645	0.366391	0.034*
H12C	0.792865	0.453602	0.400395	0.034*
C13	1.08734 (10)	0.6999 (2)	0.30884 (13)	0.0324 (4)
H13A	1.137314	0.721830	0.359870	0.049*
H13B	1.082865	0.775777	0.259110	0.049*
H13C	1.092381	0.597390	0.284035	0.049*
C14	0.87597 (10)	1.01221 (17)	0.42238 (10)	0.0233 (3)
H14A	0.914717	1.091985	0.412426	0.035*
H14B	0.872274	1.015614	0.487285	0.035*
H14C	0.819916	1.029486	0.380350	0.035*
C15	0.57190 (8)	0.75149 (16)	0.40930 (9)	0.0151 (3)
C16	0.52152 (9)	0.87994 (16)	0.37804 (9)	0.0166 (3)
C17	0.43675 (9)	0.85616 (17)	0.33349 (10)	0.0199 (3)
H17	0.401693	0.941873	0.311240	0.024*
C18	0.40206 (9)	0.70968 (18)	0.32076 (10)	0.0223 (3)
C19	0.45411 (9)	0.58466 (17)	0.35178 (10)	0.0210 (3)
H19	0.430990	0.484470	0.342404	0.025*
C20	0.53954 (9)	0.60283 (16)	0.39638 (9)	0.0176 (3)
C21	0.55692 (9)	1.03973 (16)	0.39057 (10)	0.0217 (3)
H21A	0.520413	1.108131	0.345174	0.033*
H21B	0.613724	1.039769	0.380716	0.033*
H21C	0.559652	1.075316	0.453981	0.033*
C22	0.30947 (10)	0.6871 (2)	0.27393 (14)	0.0358 (4)
H22A	0.298031	0.577958	0.261797	0.054*
H22B	0.294632	0.743469	0.214758	0.054*
H22C	0.275699	0.725370	0.314851	0.054*
C23	0.59506 (10)	0.46490 (17)	0.42671 (11)	0.0235 (3)
H23A	0.559768	0.373804	0.424544	0.035*
H23B	0.629714	0.480296	0.490622	0.035*
H23C	0.631789	0.450947	0.384670	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01580 (18)	0.0250 (2)	0.01103 (17)	0.00180 (13)	0.00354 (13)	−0.00034 (13)
N1	0.0139 (5)	0.0195 (6)	0.0125 (5)	0.0013 (4)	0.0040 (4)	0.0016 (4)
C1	0.0159 (6)	0.0117 (6)	0.0144 (6)	−0.0006 (5)	0.0042 (5)	−0.0001 (5)
C2	0.0166 (6)	0.0254 (7)	0.0145 (6)	0.0021 (6)	0.0031 (5)	0.0054 (6)
N2	0.0134 (5)	0.0200 (6)	0.0113 (5)	−0.0009 (4)	0.0029 (4)	−0.0024 (4)
C3	0.0186 (7)	0.0353 (8)	0.0132 (6)	−0.0041 (6)	0.0028 (5)	−0.0007 (6)
C4	0.0226 (7)	0.0249 (7)	0.0159 (7)	−0.0040 (6)	0.0056 (5)	−0.0050 (6)
C5	0.0189 (7)	0.0257 (7)	0.0117 (6)	−0.0007 (6)	0.0058 (5)	−0.0028 (5)
C7	0.0147 (6)	0.0204 (7)	0.0147 (6)	0.0007 (5)	0.0015 (5)	0.0010 (5)
C6	0.0127 (6)	0.0214 (7)	0.0125 (6)	0.0003 (5)	0.0025 (5)	0.0008 (5)
C9	0.0140 (6)	0.0335 (8)	0.0162 (7)	0.0012 (6)	0.0032 (5)	0.0034 (6)
C8	0.0165 (7)	0.0245 (7)	0.0174 (7)	0.0047 (6)	0.0033 (5)	0.0002 (6)
C10	0.0168 (7)	0.0252 (7)	0.0174 (7)	−0.0043 (6)	0.0027 (5)	0.0035 (6)
C11	0.0165 (6)	0.0207 (7)	0.0137 (6)	−0.0007 (5)	0.0010 (5)	0.0006 (5)
C12	0.0238 (7)	0.0192 (7)	0.0267 (8)	−0.0003 (6)	0.0088 (6)	−0.0008 (6)
C13	0.0237 (8)	0.0416 (10)	0.0369 (9)	0.0030 (7)	0.0168 (7)	0.0054 (8)
C14	0.0270 (8)	0.0193 (7)	0.0236 (7)	−0.0023 (6)	0.0066 (6)	−0.0003 (6)
C15	0.0138 (6)	0.0204 (7)	0.0120 (6)	−0.0006 (5)	0.0049 (5)	−0.0011 (5)
C16	0.0182 (7)	0.0192 (7)	0.0141 (6)	0.0007 (5)	0.0071 (5)	−0.0013 (5)
C17	0.0182 (7)	0.0241 (7)	0.0172 (7)	0.0058 (6)	0.0044 (5)	−0.0034 (6)
C18	0.0164 (7)	0.0307 (8)	0.0202 (7)	−0.0009 (6)	0.0056 (6)	−0.0075 (6)
C19	0.0192 (7)	0.0221 (7)	0.0233 (7)	−0.0053 (6)	0.0085 (6)	−0.0059 (6)
C20	0.0183 (7)	0.0195 (7)	0.0162 (6)	−0.0004 (5)	0.0068 (5)	−0.0012 (5)
C21	0.0237 (7)	0.0183 (7)	0.0237 (7)	0.0001 (6)	0.0069 (6)	−0.0007 (6)
C22	0.0169 (8)	0.0397 (10)	0.0479 (11)	0.0001 (7)	0.0030 (7)	−0.0153 (8)
C23	0.0259 (7)	0.0180 (7)	0.0264 (8)	0.0000 (6)	0.0066 (6)	0.0009 (6)

Geometric parameters (Å, º)

S1—C1	1.6887 (14)	C12—H12A	0.9800
N1—C1	1.3625 (17)	C12—H12B	0.9800
N1—C2	1.4783 (17)	C12—H12C	0.9800
N1—C6	1.4447 (17)	C13—H13A	0.9800
C1—N2	1.3611 (17)	C13—H13B	0.9800
C2—H2A	0.9900	C13—H13C	0.9800
C2—H2B	0.9900	C14—H14A	0.9800
C2—C3	1.522 (2)	C14—H14B	0.9800
N2—C5	1.4898 (16)	C14—H14C	0.9800
N2—C15	1.4454 (17)	C15—C16	1.3999 (19)
C3—H3A	0.9900	C15—C20	1.3977 (19)
C3—H3B	0.9900	C16—C17	1.392 (2)
C3—C4	1.527 (2)	C16—C21	1.505 (2)
C4—H4A	0.9900	C17—H17	0.9500
C4—H4B	0.9900	C17—C18	1.394 (2)
C4—C5	1.5245 (19)	C18—C19	1.390 (2)
C5—H5A	0.9900	C18—C22	1.511 (2)
C5—H5B	0.9900	C19—H19	0.9500
C7—C6	1.3965 (19)	C19—C20	1.396 (2)
C7—C8	1.4001 (19)	C20—C23	1.508 (2)
C7—C12	1.506 (2)	C21—H21A	0.9800
C6—C11	1.3974 (19)	C21—H21B	0.9800
C9—C8	1.388 (2)	C21—H21C	0.9800
C9—C10	1.391 (2)	C22—H22A	0.9800
C9—C13	1.510 (2)	C22—H22B	0.9800
C8—H8	0.9500	C22—H22C	0.9800
C10—H10	0.9500	C23—H23A	0.9800
C10—C11	1.3961 (19)	C23—H23B	0.9800
C11—C14	1.505 (2)	C23—H23C	0.9800
C1—N1—C2	121.92 (11)	C7—C12—H12C	109.5
C1—N1—C6	120.72 (11)	H12A—C12—H12B	109.5
C6—N1—C2	116.02 (11)	H12A—C12—H12C	109.5
N1—C1—S1	120.55 (10)	H12B—C12—H12C	109.5
N2—C1—S1	120.92 (10)	C9—C13—H13A	109.5
N2—C1—N1	118.52 (12)	C9—C13—H13B	109.5
N1—C2—H2A	109.2	C9—C13—H13C	109.5
N1—C2—H2B	109.2	H13A—C13—H13B	109.5
N1—C2—C3	112.26 (12)	H13A—C13—H13C	109.5
H2A—C2—H2B	107.9	H13B—C13—H13C	109.5
C3—C2—H2A	109.2	C11—C14—H14A	109.5
C3—C2—H2B	109.2	C11—C14—H14B	109.5
C1—N2—C5	128.18 (11)	C11—C14—H14C	109.5
C1—N2—C15	118.63 (11)	H14A—C14—H14B	109.5
C15—N2—C5	113.15 (10)	H14A—C14—H14C	109.5
C2—C3—H3A	109.7	H14B—C14—H14C	109.5
C2—C3—H3B	109.7	C16—C15—N2	119.48 (12)
C2—C3—C4	110.02 (12)	C20—C15—N2	118.55 (12)
H3A—C3—H3B	108.2	C20—C15—C16	121.94 (13)
C4—C3—H3A	109.7	C15—C16—C21	121.81 (12)
C4—C3—H3B	109.7	C17—C16—C15	117.98 (13)
C3—C4—H4A	109.1	C17—C16—C21	120.21 (13)
C3—C4—H4B	109.1	C16—C17—H17	119.2
H4A—C4—H4B	107.9	C16—C17—C18	121.61 (13)
C5—C4—C3	112.33 (12)	C18—C17—H17	119.2
C5—C4—H4A	109.1	C17—C18—C22	120.58 (14)
C5—C4—H4B	109.1	C19—C18—C17	118.87 (13)
N2—C5—C4	114.70 (11)	C19—C18—C22	120.55 (14)
N2—C5—H5A	108.6	C18—C19—H19	119.2
N2—C5—H5B	108.6	C18—C19—C20	121.55 (14)
C4—C5—H5A	108.6	C20—C19—H19	119.2
C4—C5—H5B	108.6	C15—C20—C23	121.55 (13)
H5A—C5—H5B	107.6	C19—C20—C15	118.04 (13)
C6—C7—C8	118.40 (13)	C19—C20—C23	120.38 (13)
C6—C7—C12	121.52 (12)	C16—C21—H21A	109.5
C8—C7—C12	120.07 (13)	C16—C21—H21B	109.5
C7—C6—N1	118.99 (12)	C16—C21—H21C	109.5
C7—C6—C11	121.35 (12)	H21A—C21—H21B	109.5
C11—C6—N1	119.57 (12)	H21A—C21—H21C	109.5
C8—C9—C10	118.20 (13)	H21B—C21—H21C	109.5
C8—C9—C13	121.19 (14)	C18—C22—H22A	109.5
C10—C9—C13	120.61 (14)	C18—C22—H22B	109.5
C7—C8—H8	119.1	C18—C22—H22C	109.5
C9—C8—C7	121.75 (13)	H22A—C22—H22B	109.5
C9—C8—H8	119.1	H22A—C22—H22C	109.5
C9—C10—H10	118.9	H22B—C22—H22C	109.5
C9—C10—C11	122.15 (13)	C20—C23—H23A	109.5
C11—C10—H10	118.9	C20—C23—H23B	109.5
C6—C11—C14	121.68 (12)	C20—C23—H23C	109.5
C10—C11—C6	118.12 (13)	H23A—C23—H23B	109.5
C10—C11—C14	120.19 (13)	H23A—C23—H23C	109.5
C7—C12—H12A	109.5	H23B—C23—H23C	109.5
C7—C12—H12B	109.5
S1—C1—N2—C5	−160.74 (11)	C6—N1—C1—N2	−172.91 (12)
S1—C1—N2—C15	16.83 (17)	C6—N1—C2—C3	106.84 (13)
N1—C1—N2—C5	20.1 (2)	C6—C7—C8—C9	−0.4 (2)
N1—C1—N2—C15	−162.33 (12)	C9—C10—C11—C6	−0.4 (2)
N1—C2—C3—C4	49.58 (15)	C9—C10—C11—C14	−179.36 (13)
N1—C6—C11—C10	175.13 (12)	C8—C7—C6—N1	−174.76 (12)
N1—C6—C11—C14	−6.0 (2)	C8—C7—C6—C11	1.7 (2)
C1—N1—C2—C3	−86.27 (15)	C8—C9—C10—C11	1.7 (2)
C1—N1—C6—C7	−96.59 (15)	C10—C9—C8—C7	−1.3 (2)
C1—N1—C6—C11	86.86 (16)	C12—C7—C6—N1	6.02 (19)
C1—N2—C5—C4	24.2 (2)	C12—C7—C6—C11	−177.50 (13)
C1—N2—C15—C16	−101.69 (15)	C12—C7—C8—C9	178.86 (13)
C1—N2—C15—C20	80.59 (16)	C13—C9—C8—C7	177.75 (14)
C2—N1—C1—S1	−158.36 (10)	C13—C9—C10—C11	−177.34 (14)
C2—N1—C1—N2	20.80 (19)	C15—N2—C5—C4	−153.50 (12)
C2—N1—C6—C7	70.48 (16)	C15—C16—C17—C18	0.6 (2)
C2—N1—C6—C11	−106.07 (15)	C16—C15—C20—C19	−0.7 (2)
C2—C3—C4—C5	36.75 (16)	C16—C15—C20—C23	177.42 (13)
N2—C15—C16—C17	−177.21 (11)	C16—C17—C18—C19	−1.3 (2)
N2—C15—C16—C21	3.45 (19)	C16—C17—C18—C22	178.76 (14)
N2—C15—C20—C19	176.91 (12)	C17—C18—C19—C20	1.0 (2)
N2—C15—C20—C23	−4.93 (19)	C18—C19—C20—C15	0.0 (2)
C3—C4—C5—N2	−79.12 (15)	C18—C19—C20—C23	−178.16 (13)
C5—N2—C15—C16	76.22 (15)	C20—C15—C16—C17	0.4 (2)
C5—N2—C15—C20	−101.49 (14)	C20—C15—C16—C21	−178.91 (12)
C7—C6—C11—C10	−1.3 (2)	C21—C16—C17—C18	179.97 (13)
C7—C6—C11—C14	177.58 (13)	C22—C18—C19—C20	−179.09 (14)
C6—N1—C1—S1	7.93 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···S1^i	0.99	3.01	3.7030 (15)	128
C5—H5A···S1^i	0.99	2.87	3.4858 (14)	121

Symmetry code: (i) x, −y+3/2, z+1/2.

(SDiazMesSe)

Crystal data

C23H30N2Se	Dx = 1.332 Mg m^−3
Mr = 413.45	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9854 reflections
a = 17.4279 (4) Å	θ = 2.2–27.1°
b = 15.2522 (4) Å	µ = 1.83 mm^−1
c = 31.0253 (7) Å	T = 100 K
V = 8247.0 (3) Å^3	Block, colourless
Z = 16	0.08 × 0.07 × 0.07 mm
F(000) = 3456

Data collection

Bruker D8 Venture Photon 2 diffractometer	7294 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.072
φ and ω scans	θmax = 27.1°, θmin = 2.2°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −22→22
Tmin = 0.697, Tmax = 0.746	k = −19→19
72880 measured reflections	l = −39→36
9109 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.078	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0255P)^2 + 7.8329P] where P = (Fo^2 + 2Fc^2)/3
9109 reflections	(Δ/σ)max = 0.003
481 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Se1	0.24756 (2)	0.41747 (2)	0.61765 (2)	0.01788 (6)
N1	0.27122 (10)	0.59242 (11)	0.64196 (6)	0.0143 (4)
N2	0.37745 (10)	0.52283 (11)	0.61141 (6)	0.0138 (4)
C1	0.30350 (12)	0.51984 (13)	0.62404 (7)	0.0128 (4)
C2	0.29679 (14)	0.68578 (14)	0.63787 (8)	0.0204 (5)
H2A	0.327269	0.701351	0.663691	0.024*
H2B	0.250851	0.723944	0.637512	0.024*
C3	0.34430 (14)	0.70498 (15)	0.59812 (8)	0.0221 (5)
H3A	0.343938	0.768926	0.592654	0.027*
H3B	0.320547	0.675730	0.572954	0.027*
C4	0.42728 (13)	0.67393 (15)	0.60253 (9)	0.0238 (5)
H4A	0.449508	0.664614	0.573528	0.029*
H4B	0.457907	0.719634	0.617276	0.029*
C5	0.43137 (13)	0.58965 (15)	0.62790 (8)	0.0187 (5)
H5A	0.484289	0.566240	0.626511	0.022*
H5B	0.419360	0.601968	0.658497	0.022*
C6	0.20033 (12)	0.58361 (14)	0.66556 (7)	0.0145 (4)
C7	0.13045 (13)	0.60225 (14)	0.64548 (7)	0.0172 (5)
C8	0.06369 (13)	0.59627 (15)	0.66997 (8)	0.0200 (5)
H8	0.015787	0.607763	0.656497	0.024*
C9	0.06462 (14)	0.57420 (15)	0.71320 (8)	0.0212 (5)
C10	0.13509 (15)	0.55836 (16)	0.73235 (8)	0.0227 (5)
H10	0.136642	0.543746	0.762105	0.027*
C11	0.20354 (13)	0.56311 (15)	0.70954 (7)	0.0183 (5)
C12	0.12753 (15)	0.62679 (18)	0.59865 (8)	0.0270 (6)
H12A	0.076094	0.614956	0.587289	0.041*
H12B	0.165340	0.592139	0.582642	0.041*
H12C	0.139241	0.689297	0.595461	0.041*
C13	−0.00917 (15)	0.56505 (17)	0.73841 (9)	0.0315 (6)
H13A	−0.050010	0.597953	0.723927	0.047*
H13B	−0.001831	0.588237	0.767578	0.047*
H13C	−0.023512	0.503008	0.740068	0.047*
C14	0.27916 (15)	0.54467 (19)	0.73116 (8)	0.0301 (6)
H14A	0.272270	0.545175	0.762508	0.045*
H14B	0.316431	0.589797	0.722959	0.045*
H14C	0.298022	0.487018	0.722085	0.045*
C15	0.41106 (12)	0.45437 (13)	0.58528 (7)	0.0137 (4)
C16	0.40346 (12)	0.45655 (14)	0.54064 (7)	0.0150 (4)
C17	0.43903 (13)	0.39130 (15)	0.51629 (8)	0.0177 (5)
H17	0.434344	0.392502	0.485785	0.021*
C18	0.48113 (12)	0.32459 (15)	0.53552 (7)	0.0172 (4)
C19	0.48825 (12)	0.32494 (14)	0.58018 (7)	0.0173 (5)
H19	0.517563	0.280194	0.593692	0.021*
C20	0.45381 (13)	0.38870 (15)	0.60559 (7)	0.0164 (5)
C21	0.35540 (14)	0.52488 (15)	0.51794 (7)	0.0204 (5)
H21A	0.304510	0.527578	0.531307	0.031*
H21B	0.350099	0.509166	0.487456	0.031*
H21C	0.380433	0.582211	0.520332	0.031*
C22	0.51597 (15)	0.25184 (16)	0.50905 (8)	0.0239 (5)
H22A	0.571760	0.259461	0.507823	0.036*
H22B	0.494851	0.253584	0.479789	0.036*
H22C	0.503932	0.195193	0.522340	0.036*
C23	0.45985 (15)	0.38390 (17)	0.65411 (8)	0.0269 (6)
H23A	0.481764	0.327216	0.662465	0.040*
H23B	0.408672	0.390103	0.666838	0.040*
H23C	0.493036	0.431265	0.664509	0.040*
Se2	0.36720 (2)	0.32364 (2)	0.37637 (2)	0.01701 (6)
N3	0.26364 (10)	0.19889 (11)	0.40670 (6)	0.0127 (4)
N4	0.34705 (10)	0.14818 (11)	0.35318 (6)	0.0132 (4)
C24	0.32192 (12)	0.21407 (13)	0.37873 (7)	0.0126 (4)
C25	0.24357 (14)	0.10973 (14)	0.42179 (7)	0.0176 (5)
H25A	0.218801	0.114125	0.450422	0.021*
H25B	0.291279	0.075204	0.425249	0.021*
C26	0.19040 (14)	0.06168 (15)	0.39144 (8)	0.0214 (5)
H26A	0.138654	0.088325	0.392685	0.026*
H26B	0.186012	−0.000385	0.400452	0.026*
C27	0.22096 (14)	0.06627 (16)	0.34535 (8)	0.0219 (5)
H27A	0.199879	0.016535	0.328610	0.026*
H27B	0.202784	0.121191	0.331740	0.026*
C28	0.30788 (13)	0.06338 (15)	0.34332 (8)	0.0200 (5)
H28A	0.326324	0.018512	0.363918	0.024*
H28B	0.323294	0.044343	0.314064	0.024*
C29	0.22759 (12)	0.27116 (13)	0.42915 (7)	0.0129 (4)
C30	0.24624 (13)	0.28639 (14)	0.47206 (7)	0.0151 (4)
C31	0.20980 (13)	0.35541 (15)	0.49346 (7)	0.0175 (5)
H31	0.222695	0.367262	0.522634	0.021*
C32	0.15514 (13)	0.40709 (14)	0.47306 (8)	0.0188 (5)
C33	0.13732 (13)	0.38895 (14)	0.43025 (7)	0.0178 (5)
H33	0.099708	0.423660	0.416105	0.021*
C34	0.17286 (12)	0.32151 (14)	0.40748 (7)	0.0146 (4)
C35	0.30545 (14)	0.23231 (16)	0.49537 (8)	0.0229 (5)
H35A	0.282157	0.177285	0.505110	0.034*
H35B	0.324559	0.265048	0.520338	0.034*
H35C	0.348155	0.219400	0.475826	0.034*
C36	0.11402 (15)	0.47840 (16)	0.49765 (9)	0.0272 (6)
H36A	0.091077	0.519918	0.477284	0.041*
H36B	0.150684	0.509297	0.516172	0.041*
H36C	0.073616	0.452268	0.515473	0.041*
C37	0.15406 (13)	0.30592 (15)	0.36075 (7)	0.0193 (5)
H37A	0.113906	0.346878	0.351613	0.029*
H37B	0.135889	0.245593	0.356992	0.029*
H37C	0.200142	0.315125	0.343225	0.029*
C38	0.41706 (12)	0.15949 (13)	0.32882 (7)	0.0139 (4)
C39	0.48655 (13)	0.13351 (13)	0.34659 (7)	0.0142 (4)
C40	0.55311 (13)	0.14136 (15)	0.32181 (8)	0.0187 (5)
H40	0.600806	0.122810	0.333495	0.022*
C41	0.55078 (13)	0.17592 (15)	0.28026 (8)	0.0200 (5)
C42	0.47984 (14)	0.20091 (15)	0.26341 (7)	0.0197 (5)
H42	0.477836	0.224709	0.235132	0.024*
C43	0.41222 (13)	0.19218 (14)	0.28649 (7)	0.0162 (5)
C44	0.49173 (14)	0.09976 (15)	0.39223 (7)	0.0197 (5)
H44A	0.477852	0.146695	0.412342	0.029*
H44B	0.544301	0.080328	0.398097	0.029*
H44C	0.456397	0.050325	0.395882	0.029*
C45	0.62329 (15)	0.18428 (18)	0.25400 (9)	0.0309 (6)
H45A	0.617548	0.151658	0.226983	0.046*
H45B	0.666578	0.160362	0.270386	0.046*
H45C	0.632851	0.246239	0.247595	0.046*
C46	0.33635 (14)	0.21877 (16)	0.26720 (8)	0.0234 (5)
H46A	0.344789	0.243312	0.238394	0.035*
H46B	0.312021	0.262979	0.285600	0.035*
H46C	0.302904	0.167302	0.265054	0.035*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.01492 (11)	0.01341 (11)	0.02531 (12)	−0.00392 (8)	0.00470 (10)	−0.00215 (9)
N1	0.0126 (9)	0.0128 (9)	0.0176 (9)	−0.0016 (7)	0.0028 (7)	−0.0002 (7)
N2	0.0118 (9)	0.0123 (9)	0.0175 (9)	−0.0008 (7)	−0.0010 (7)	−0.0003 (7)
C1	0.0146 (10)	0.0121 (10)	0.0117 (10)	−0.0003 (8)	−0.0002 (8)	0.0030 (8)
C2	0.0213 (12)	0.0113 (11)	0.0285 (13)	−0.0006 (9)	0.0037 (10)	−0.0007 (9)
C3	0.0227 (12)	0.0133 (11)	0.0303 (13)	−0.0027 (9)	0.0051 (10)	0.0040 (10)
C4	0.0184 (12)	0.0167 (11)	0.0362 (14)	−0.0065 (9)	0.0047 (10)	−0.0020 (11)
C5	0.0121 (10)	0.0195 (11)	0.0246 (12)	−0.0023 (9)	−0.0030 (9)	−0.0046 (10)
C6	0.0137 (11)	0.0134 (10)	0.0163 (11)	0.0005 (8)	0.0020 (9)	0.0014 (9)
C7	0.0184 (11)	0.0155 (11)	0.0176 (11)	0.0036 (9)	−0.0003 (9)	−0.0005 (9)
C8	0.0155 (11)	0.0192 (12)	0.0252 (13)	0.0039 (9)	0.0009 (10)	−0.0015 (10)
C9	0.0203 (12)	0.0161 (11)	0.0272 (13)	0.0007 (9)	0.0076 (10)	−0.0023 (10)
C10	0.0297 (14)	0.0228 (12)	0.0155 (11)	0.0010 (10)	0.0053 (10)	0.0025 (9)
C11	0.0197 (12)	0.0165 (11)	0.0187 (12)	0.0007 (9)	−0.0005 (9)	0.0000 (9)
C12	0.0229 (13)	0.0377 (15)	0.0206 (12)	0.0080 (11)	−0.0019 (11)	0.0033 (11)
C13	0.0275 (14)	0.0296 (14)	0.0375 (16)	0.0020 (11)	0.0176 (12)	0.0018 (12)
C14	0.0242 (14)	0.0461 (17)	0.0200 (13)	0.0047 (12)	−0.0040 (11)	0.0062 (12)
C15	0.0102 (10)	0.0117 (10)	0.0192 (11)	−0.0005 (8)	0.0017 (9)	−0.0002 (9)
C16	0.0108 (10)	0.0152 (11)	0.0189 (11)	−0.0006 (8)	−0.0003 (9)	0.0054 (9)
C17	0.0156 (11)	0.0188 (11)	0.0188 (11)	0.0010 (9)	0.0020 (9)	0.0034 (9)
C18	0.0133 (10)	0.0170 (11)	0.0214 (11)	−0.0001 (9)	0.0044 (9)	0.0017 (9)
C19	0.0136 (10)	0.0163 (11)	0.0220 (11)	0.0040 (9)	−0.0016 (9)	0.0050 (9)
C20	0.0148 (11)	0.0187 (11)	0.0158 (11)	0.0000 (9)	−0.0017 (9)	0.0036 (9)
C21	0.0233 (12)	0.0195 (11)	0.0185 (11)	0.0068 (10)	−0.0018 (10)	0.0035 (9)
C22	0.0268 (13)	0.0216 (12)	0.0234 (13)	0.0079 (10)	0.0047 (10)	0.0015 (10)
C23	0.0314 (14)	0.0307 (14)	0.0188 (12)	0.0123 (11)	−0.0028 (11)	0.0036 (10)
Se2	0.01419 (11)	0.01075 (10)	0.02608 (12)	−0.00273 (8)	0.00550 (9)	−0.00285 (9)
N3	0.0130 (9)	0.0098 (8)	0.0153 (9)	−0.0005 (7)	0.0014 (7)	−0.0003 (7)
N4	0.0121 (9)	0.0111 (8)	0.0166 (9)	−0.0023 (7)	0.0014 (7)	−0.0033 (7)
C24	0.0115 (10)	0.0119 (10)	0.0144 (10)	0.0016 (8)	−0.0034 (9)	−0.0003 (8)
C25	0.0238 (12)	0.0103 (10)	0.0187 (11)	−0.0030 (9)	0.0035 (10)	0.0012 (8)
C26	0.0215 (12)	0.0163 (11)	0.0263 (13)	−0.0061 (9)	0.0044 (10)	−0.0021 (10)
C27	0.0190 (12)	0.0231 (12)	0.0235 (13)	−0.0073 (9)	−0.0016 (10)	−0.0058 (10)
C28	0.0206 (12)	0.0170 (11)	0.0222 (12)	−0.0026 (9)	0.0018 (10)	−0.0072 (9)
C29	0.0113 (10)	0.0101 (10)	0.0172 (11)	−0.0014 (8)	0.0022 (8)	−0.0015 (8)
C30	0.0134 (10)	0.0155 (11)	0.0164 (10)	−0.0055 (9)	0.0020 (9)	−0.0003 (8)
C31	0.0174 (11)	0.0184 (11)	0.0165 (11)	−0.0064 (9)	0.0012 (9)	−0.0035 (9)
C32	0.0177 (11)	0.0129 (10)	0.0257 (12)	−0.0032 (9)	0.0087 (10)	−0.0024 (9)
C33	0.0128 (11)	0.0170 (11)	0.0235 (12)	0.0013 (9)	0.0055 (9)	0.0026 (9)
C34	0.0115 (10)	0.0145 (10)	0.0178 (11)	−0.0030 (8)	0.0037 (8)	0.0007 (9)
C35	0.0226 (13)	0.0242 (13)	0.0219 (12)	0.0000 (10)	−0.0056 (10)	−0.0003 (10)
C36	0.0278 (14)	0.0213 (12)	0.0326 (14)	0.0005 (10)	0.0114 (11)	−0.0071 (11)
C37	0.0159 (11)	0.0243 (12)	0.0176 (11)	0.0037 (9)	−0.0019 (9)	0.0004 (9)
C38	0.0140 (10)	0.0106 (10)	0.0172 (11)	−0.0002 (8)	0.0033 (9)	−0.0047 (8)
C39	0.0174 (11)	0.0109 (10)	0.0143 (10)	0.0004 (8)	−0.0004 (9)	−0.0032 (8)
C40	0.0165 (11)	0.0184 (11)	0.0211 (12)	0.0024 (9)	0.0008 (9)	−0.0044 (9)
C41	0.0191 (12)	0.0194 (11)	0.0214 (12)	−0.0014 (10)	0.0060 (9)	−0.0071 (10)
C42	0.0269 (13)	0.0191 (11)	0.0131 (11)	−0.0016 (10)	0.0026 (10)	−0.0014 (9)
C43	0.0192 (11)	0.0117 (11)	0.0176 (11)	0.0002 (8)	−0.0005 (9)	−0.0025 (8)
C44	0.0214 (12)	0.0195 (12)	0.0181 (11)	−0.0006 (9)	−0.0021 (9)	0.0008 (9)
C45	0.0255 (13)	0.0373 (15)	0.0298 (14)	−0.0017 (12)	0.0127 (11)	−0.0022 (12)
C46	0.0196 (12)	0.0263 (13)	0.0243 (13)	0.0023 (10)	−0.0050 (10)	0.0040 (10)

Geometric parameters (Å, º)

Se1—C1	1.851 (2)	Se2—C24	1.849 (2)
N1—C1	1.360 (3)	N3—C24	1.356 (3)
N1—C2	1.498 (3)	N3—C25	1.480 (3)
N1—C6	1.442 (3)	N3—C29	1.447 (3)
N2—C1	1.348 (3)	N4—C24	1.353 (3)
N2—C5	1.478 (3)	N4—C28	1.494 (3)
N2—C15	1.446 (3)	N4—C38	1.446 (3)
C2—H2A	0.9900	C25—H25A	0.9900
C2—H2B	0.9900	C25—H25B	0.9900
C2—C3	1.514 (3)	C25—C26	1.511 (3)
C3—H3A	0.9900	C26—H26A	0.9900
C3—H3B	0.9900	C26—H26B	0.9900
C3—C4	1.528 (3)	C26—C27	1.528 (3)
C4—H4A	0.9900	C27—H27A	0.9900
C4—H4B	0.9900	C27—H27B	0.9900
C4—C5	1.509 (3)	C27—C28	1.517 (3)
C5—H5A	0.9900	C28—H28A	0.9900
C5—H5B	0.9900	C28—H28B	0.9900
C6—C7	1.397 (3)	C29—C30	1.390 (3)
C6—C11	1.401 (3)	C29—C34	1.397 (3)
C7—C8	1.393 (3)	C30—C31	1.397 (3)
C7—C12	1.501 (3)	C30—C35	1.506 (3)
C8—H8	0.9500	C31—H31	0.9500
C8—C9	1.383 (3)	C31—C32	1.389 (3)
C9—C10	1.385 (3)	C32—C33	1.392 (3)
C9—C13	1.512 (3)	C32—C36	1.509 (3)
C10—H10	0.9500	C33—H33	0.9500
C10—C11	1.389 (3)	C33—C34	1.393 (3)
C11—C14	1.505 (3)	C34—C37	1.505 (3)
C12—H12A	0.9800	C35—H35A	0.9800
C12—H12B	0.9800	C35—H35B	0.9800
C12—H12C	0.9800	C35—H35C	0.9800
C13—H13A	0.9800	C36—H36A	0.9800
C13—H13B	0.9800	C36—H36B	0.9800
C13—H13C	0.9800	C36—H36C	0.9800
C14—H14A	0.9800	C37—H37A	0.9800
C14—H14B	0.9800	C37—H37B	0.9800
C14—H14C	0.9800	C37—H37C	0.9800
C15—C16	1.392 (3)	C38—C39	1.388 (3)
C15—C20	1.398 (3)	C38—C43	1.407 (3)
C16—C17	1.395 (3)	C39—C40	1.397 (3)
C16—C21	1.511 (3)	C39—C44	1.509 (3)
C17—H17	0.9500	C40—H40	0.9500
C17—C18	1.389 (3)	C40—C41	1.393 (3)
C18—C19	1.391 (3)	C41—C42	1.395 (3)
C18—C22	1.508 (3)	C41—C45	1.509 (3)
C19—H19	0.9500	C42—H42	0.9500
C19—C20	1.388 (3)	C42—C43	1.385 (3)
C20—C23	1.511 (3)	C43—C46	1.507 (3)
C21—H21A	0.9800	C44—H44A	0.9800
C21—H21B	0.9800	C44—H44B	0.9800
C21—H21C	0.9800	C44—H44C	0.9800
C22—H22A	0.9800	C45—H45A	0.9800
C22—H22B	0.9800	C45—H45B	0.9800
C22—H22C	0.9800	C45—H45C	0.9800
C23—H23A	0.9800	C46—H46A	0.9800
C23—H23B	0.9800	C46—H46B	0.9800
C23—H23C	0.9800	C46—H46C	0.9800
C1—N1—C2	128.02 (18)	C24—N3—C25	122.43 (17)
C1—N1—C6	119.07 (17)	C24—N3—C29	120.21 (17)
C6—N1—C2	112.73 (17)	C29—N3—C25	116.43 (17)
C1—N2—C5	122.05 (18)	C24—N4—C28	127.97 (18)
C1—N2—C15	121.73 (18)	C24—N4—C38	119.40 (17)
C15—N2—C5	115.77 (17)	C38—N4—C28	112.45 (17)
N1—C1—Se1	120.80 (15)	N3—C24—Se2	119.94 (15)
N2—C1—Se1	120.06 (15)	N4—C24—Se2	120.67 (16)
N2—C1—N1	119.13 (18)	N4—C24—N3	119.39 (18)
N1—C2—H2A	108.6	N3—C25—H25A	108.9
N1—C2—H2B	108.6	N3—C25—H25B	108.9
N1—C2—C3	114.56 (19)	N3—C25—C26	113.18 (18)
H2A—C2—H2B	107.6	H25A—C25—H25B	107.8
C3—C2—H2A	108.6	C26—C25—H25A	108.9
C3—C2—H2B	108.6	C26—C25—H25B	108.9
C2—C3—H3A	109.1	C25—C26—H26A	109.6
C2—C3—H3B	109.1	C25—C26—H26B	109.6
C2—C3—C4	112.6 (2)	C25—C26—C27	110.33 (19)
H3A—C3—H3B	107.8	H26A—C26—H26B	108.1
C4—C3—H3A	109.1	C27—C26—H26A	109.6
C4—C3—H3B	109.1	C27—C26—H26B	109.6
C3—C4—H4A	109.5	C26—C27—H27A	109.1
C3—C4—H4B	109.5	C26—C27—H27B	109.1
H4A—C4—H4B	108.1	H27A—C27—H27B	107.8
C5—C4—C3	110.82 (19)	C28—C27—C26	112.7 (2)
C5—C4—H4A	109.5	C28—C27—H27A	109.1
C5—C4—H4B	109.5	C28—C27—H27B	109.1
N2—C5—C4	112.15 (19)	N4—C28—C27	115.00 (19)
N2—C5—H5A	109.2	N4—C28—H28A	108.5
N2—C5—H5B	109.2	N4—C28—H28B	108.5
C4—C5—H5A	109.2	C27—C28—H28A	108.5
C4—C5—H5B	109.2	C27—C28—H28B	108.5
H5A—C5—H5B	107.9	H28A—C28—H28B	107.5
C7—C6—N1	120.07 (19)	C30—C29—N3	119.11 (19)
C7—C6—C11	121.0 (2)	C30—C29—C34	121.9 (2)
C11—C6—N1	118.76 (19)	C34—C29—N3	118.92 (19)
C6—C7—C12	120.8 (2)	C29—C30—C31	118.3 (2)
C8—C7—C6	118.1 (2)	C29—C30—C35	121.9 (2)
C8—C7—C12	121.1 (2)	C31—C30—C35	119.7 (2)
C7—C8—H8	118.8	C30—C31—H31	119.2
C9—C8—C7	122.4 (2)	C32—C31—C30	121.5 (2)
C9—C8—H8	118.8	C32—C31—H31	119.2
C8—C9—C10	118.0 (2)	C31—C32—C33	118.4 (2)
C8—C9—C13	121.0 (2)	C31—C32—C36	120.3 (2)
C10—C9—C13	121.1 (2)	C33—C32—C36	121.3 (2)
C9—C10—H10	118.9	C32—C33—H33	118.9
C9—C10—C11	122.3 (2)	C32—C33—C34	122.1 (2)
C11—C10—H10	118.9	C34—C33—H33	118.9
C6—C11—C14	120.7 (2)	C29—C34—C37	121.69 (19)
C10—C11—C6	118.3 (2)	C33—C34—C29	117.7 (2)
C10—C11—C14	121.0 (2)	C33—C34—C37	120.5 (2)
C7—C12—H12A	109.5	C30—C35—H35A	109.5
C7—C12—H12B	109.5	C30—C35—H35B	109.5
C7—C12—H12C	109.5	C30—C35—H35C	109.5
H12A—C12—H12B	109.5	H35A—C35—H35B	109.5
H12A—C12—H12C	109.5	H35A—C35—H35C	109.5
H12B—C12—H12C	109.5	H35B—C35—H35C	109.5
C9—C13—H13A	109.5	C32—C36—H36A	109.5
C9—C13—H13B	109.5	C32—C36—H36B	109.5
C9—C13—H13C	109.5	C32—C36—H36C	109.5
H13A—C13—H13B	109.5	H36A—C36—H36B	109.5
H13A—C13—H13C	109.5	H36A—C36—H36C	109.5
H13B—C13—H13C	109.5	H36B—C36—H36C	109.5
C11—C14—H14A	109.5	C34—C37—H37A	109.5
C11—C14—H14B	109.5	C34—C37—H37B	109.5
C11—C14—H14C	109.5	C34—C37—H37C	109.5
H14A—C14—H14B	109.5	H37A—C37—H37B	109.5
H14A—C14—H14C	109.5	H37A—C37—H37C	109.5
H14B—C14—H14C	109.5	H37B—C37—H37C	109.5
C16—C15—N2	120.15 (19)	C39—C38—N4	119.64 (19)
C16—C15—C20	121.1 (2)	C39—C38—C43	121.6 (2)
C20—C15—N2	118.72 (19)	C43—C38—N4	118.66 (19)
C15—C16—C17	118.7 (2)	C38—C39—C40	118.8 (2)
C15—C16—C21	122.2 (2)	C38—C39—C44	121.5 (2)
C17—C16—C21	119.1 (2)	C40—C39—C44	119.7 (2)
C16—C17—H17	119.2	C39—C40—H40	119.4
C18—C17—C16	121.6 (2)	C41—C40—C39	121.2 (2)
C18—C17—H17	119.2	C41—C40—H40	119.4
C17—C18—C19	118.2 (2)	C40—C41—C42	118.4 (2)
C17—C18—C22	121.2 (2)	C40—C41—C45	120.5 (2)
C19—C18—C22	120.6 (2)	C42—C41—C45	121.1 (2)
C18—C19—H19	119.0	C41—C42—H42	118.9
C20—C19—C18	122.0 (2)	C43—C42—C41	122.3 (2)
C20—C19—H19	119.0	C43—C42—H42	118.9
C15—C20—C23	121.4 (2)	C38—C43—C46	121.2 (2)
C19—C20—C15	118.4 (2)	C42—C43—C38	117.7 (2)
C19—C20—C23	120.1 (2)	C42—C43—C46	121.0 (2)
C16—C21—H21A	109.5	C39—C44—H44A	109.5
C16—C21—H21B	109.5	C39—C44—H44B	109.5
C16—C21—H21C	109.5	C39—C44—H44C	109.5
H21A—C21—H21B	109.5	H44A—C44—H44B	109.5
H21A—C21—H21C	109.5	H44A—C44—H44C	109.5
H21B—C21—H21C	109.5	H44B—C44—H44C	109.5
C18—C22—H22A	109.5	C41—C45—H45A	109.5
C18—C22—H22B	109.5	C41—C45—H45B	109.5
C18—C22—H22C	109.5	C41—C45—H45C	109.5
H22A—C22—H22B	109.5	H45A—C45—H45B	109.5
H22A—C22—H22C	109.5	H45A—C45—H45C	109.5
H22B—C22—H22C	109.5	H45B—C45—H45C	109.5
C20—C23—H23A	109.5	C43—C46—H46A	109.5
C20—C23—H23B	109.5	C43—C46—H46B	109.5
C20—C23—H23C	109.5	C43—C46—H46C	109.5
H23A—C23—H23B	109.5	H46A—C46—H46B	109.5
H23A—C23—H23C	109.5	H46A—C46—H46C	109.5
H23B—C23—H23C	109.5	H46B—C46—H46C	109.5
N1—C2—C3—C4	−77.6 (3)	N3—C25—C26—C27	49.7 (3)
N1—C6—C7—C8	−177.5 (2)	N3—C29—C30—C31	−178.80 (19)
N1—C6—C7—C12	3.4 (3)	N3—C29—C30—C35	2.7 (3)
N1—C6—C11—C10	177.4 (2)	N3—C29—C34—C33	178.04 (18)
N1—C6—C11—C14	−4.0 (3)	N3—C29—C34—C37	−3.7 (3)
N2—C15—C16—C17	177.61 (19)	N4—C38—C39—C40	177.18 (19)
N2—C15—C16—C21	−5.0 (3)	N4—C38—C39—C44	−4.6 (3)
N2—C15—C20—C19	−177.70 (19)	N4—C38—C43—C42	−178.76 (19)
N2—C15—C20—C23	5.1 (3)	N4—C38—C43—C46	2.6 (3)
C1—N1—C2—C3	23.4 (3)	C24—N3—C25—C26	−85.0 (3)
C1—N1—C6—C7	−97.6 (2)	C24—N3—C29—C30	−102.6 (2)
C1—N1—C6—C11	87.5 (3)	C24—N3—C29—C34	79.8 (3)
C1—N2—C5—C4	−85.3 (3)	C24—N4—C28—C27	28.3 (3)
C1—N2—C15—C16	84.9 (3)	C24—N4—C38—C39	91.4 (2)
C1—N2—C15—C20	−97.8 (2)	C24—N4—C38—C43	−92.1 (2)
C2—N1—C1—Se1	−159.59 (18)	C25—N3—C24—Se2	−157.52 (16)
C2—N1—C1—N2	21.3 (3)	C25—N3—C24—N4	21.6 (3)
C2—N1—C6—C7	78.0 (3)	C25—N3—C29—C30	66.6 (3)
C2—N1—C6—C11	−96.9 (2)	C25—N3—C29—C34	−111.0 (2)
C2—C3—C4—C5	35.7 (3)	C25—C26—C27—C28	35.3 (3)
C3—C4—C5—N2	50.3 (3)	C26—C27—C28—N4	−79.3 (3)
C5—N2—C1—Se1	−159.66 (16)	C28—N4—C24—Se2	−165.05 (17)
C5—N2—C1—N1	19.5 (3)	C28—N4—C24—N3	15.9 (3)
C5—N2—C15—C16	−102.6 (2)	C28—N4—C38—C39	−93.1 (2)
C5—N2—C15—C20	74.6 (2)	C28—N4—C38—C43	83.3 (2)
C6—N1—C1—Se1	15.3 (3)	C29—N3—C24—Se2	11.0 (3)
C6—N1—C1—N2	−163.81 (19)	C29—N3—C24—N4	−169.90 (19)
C6—N1—C2—C3	−151.8 (2)	C29—N3—C25—C26	106.1 (2)
C6—C7—C8—C9	1.1 (3)	C29—C30—C31—C32	1.2 (3)
C7—C6—C11—C10	2.5 (3)	C30—C29—C34—C33	0.5 (3)
C7—C6—C11—C14	−178.9 (2)	C30—C29—C34—C37	178.7 (2)
C7—C8—C9—C10	0.5 (3)	C30—C31—C32—C33	−0.3 (3)
C7—C8—C9—C13	−177.7 (2)	C30—C31—C32—C36	177.1 (2)
C8—C9—C10—C11	−0.7 (4)	C31—C32—C33—C34	−0.5 (3)
C9—C10—C11—C6	−0.8 (4)	C32—C33—C34—C29	0.4 (3)
C9—C10—C11—C14	−179.4 (2)	C32—C33—C34—C37	−177.8 (2)
C11—C6—C7—C8	−2.7 (3)	C34—C29—C30—C31	−1.3 (3)
C11—C6—C7—C12	178.2 (2)	C34—C29—C30—C35	−179.8 (2)
C12—C7—C8—C9	−179.7 (2)	C35—C30—C31—C32	179.7 (2)
C13—C9—C10—C11	177.6 (2)	C36—C32—C33—C34	−177.8 (2)
C15—N2—C1—Se1	12.3 (3)	C38—N4—C24—Se2	9.6 (3)
C15—N2—C1—N1	−168.57 (19)	C38—N4—C24—N3	−169.51 (19)
C15—N2—C5—C4	102.3 (2)	C38—N4—C28—C27	−146.7 (2)
C15—C16—C17—C18	0.3 (3)	C38—C39—C40—C41	1.1 (3)
C16—C15—C20—C19	−0.5 (3)	C39—C38—C43—C42	−2.4 (3)
C16—C15—C20—C23	−177.7 (2)	C39—C38—C43—C46	178.9 (2)
C16—C17—C18—C19	−1.0 (3)	C39—C40—C41—C42	−1.4 (3)
C16—C17—C18—C22	176.9 (2)	C39—C40—C41—C45	179.7 (2)
C17—C18—C19—C20	1.0 (3)	C40—C41—C42—C43	−0.2 (3)
C18—C19—C20—C15	−0.2 (3)	C41—C42—C43—C38	2.1 (3)
C18—C19—C20—C23	177.0 (2)	C41—C42—C43—C46	−179.3 (2)
C20—C15—C16—C17	0.4 (3)	C43—C38—C39—C40	0.9 (3)
C20—C15—C16—C21	177.9 (2)	C43—C38—C39—C44	179.1 (2)
C21—C16—C17—C18	−177.2 (2)	C44—C39—C40—C41	−177.1 (2)
C22—C18—C19—C20	−176.9 (2)	C45—C41—C42—C43	178.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···Se1^i	0.99	3.02	3.671 (2)	125
C3—H3A···Se1^i	0.99	2.88	3.665 (2)	137
C4—H4B···Se2^ii	0.99	3.12	3.641 (2)	114
C5—H5A···Se2^ii	0.99	3.09	3.754 (2)	126
C26—H26B···Se2^iii	0.99	2.94	3.796 (2)	146

Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1/2, y−1/2, z.

(SDiazMesS_MeCN)

Crystal data

C23H30N2S·C2H3N	F(000) = 880
Mr = 407.60	Dx = 1.200 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.0884 (6) Å	Cell parameters from 9891 reflections
b = 12.9760 (5) Å	θ = 2.3–27.5°
c = 14.4293 (7) Å	µ = 0.16 mm^−1
β = 113.028 (2)°	T = 100 K
V = 2255.32 (18) Å^3	Plank, colourless
Z = 4	0.26 × 0.17 × 0.10 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	4419 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.046
φ and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −16→17
Tmin = 0.711, Tmax = 0.746	k = −16→16
34671 measured reflections	l = −18→18
5148 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0294P)^2 + 1.5344P] where P = (Fo^2 + 2Fc^2)/3
5148 reflections	(Δ/σ)max = 0.001
288 parameters	Δρmax = 0.28 e Å^−3
36 restraints	Δρmin = −0.21 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.43804 (3)	0.35053 (3)	0.58591 (3)	0.02002 (9)
N1	0.28488 (9)	0.23910 (8)	0.61966 (8)	0.0165 (2)
N2	0.46730 (9)	0.20752 (8)	0.72720 (9)	0.0187 (2)
N3	0.09785 (14)	0.67080 (12)	0.36918 (13)	0.0476 (4)
C1	0.39454 (10)	0.26151 (10)	0.64704 (10)	0.0166 (3)
C2	0.23875 (11)	0.20489 (10)	0.69367 (10)	0.0197 (3)
H2A	0.158630	0.221813	0.666660	0.024*
H2B	0.275153	0.244855	0.756507	0.024*
C3	0.25226 (12)	0.09117 (11)	0.71954 (12)	0.0244 (3)	0.853 (4)
H3A	0.228597	0.050171	0.656754	0.029*	0.853 (4)
H3B	0.204117	0.072263	0.755400	0.029*	0.853 (4)
C4	0.37427 (14)	0.06553 (13)	0.78649 (15)	0.0222 (4)	0.853 (4)
H4A	0.396298	0.103339	0.850990	0.027*	0.853 (4)
H4B	0.381061	−0.009156	0.801739	0.027*	0.853 (4)
C5	0.45187 (13)	0.09440 (12)	0.73532 (14)	0.0184 (4)	0.853 (4)
H5A	0.525312	0.062796	0.773239	0.022*	0.853 (4)
H5B	0.422643	0.064450	0.666758	0.022*	0.853 (4)
C3B	0.25226 (12)	0.09117 (11)	0.71954 (12)	0.0244 (3)	0.147 (4)
H3BA	0.246800	0.080709	0.785409	0.029*	0.147 (4)
H3BB	0.190672	0.052680	0.668254	0.029*	0.147 (4)
C4B	0.3582 (8)	0.0489 (7)	0.7244 (9)	0.023 (2)	0.147 (4)
H4BA	0.359614	0.046335	0.656333	0.027*	0.147 (4)
H4BB	0.369209	−0.021765	0.752537	0.027*	0.147 (4)
C5B	0.4460 (8)	0.1189 (8)	0.7908 (8)	0.020 (2)	0.147 (4)
H5BA	0.515448	0.079555	0.825370	0.024*	0.147 (4)
H5BB	0.422805	0.148530	0.842708	0.024*	0.147 (4)
C6	0.20570 (10)	0.28179 (10)	0.52689 (10)	0.0163 (3)
C7	0.15783 (10)	0.37797 (10)	0.52853 (10)	0.0184 (3)
C8	0.08166 (10)	0.41758 (10)	0.43835 (10)	0.0192 (3)
H8	0.048292	0.482545	0.438570	0.023*
C9	0.05303 (10)	0.36447 (10)	0.34774 (10)	0.0187 (3)
C10	0.10009 (11)	0.26778 (10)	0.34924 (10)	0.0185 (3)
H10	0.079210	0.229709	0.288364	0.022*
C11	0.17719 (10)	0.22557 (10)	0.43810 (10)	0.0173 (3)
C12	0.18995 (12)	0.43966 (11)	0.62429 (11)	0.0246 (3)
H12A	0.167502	0.511629	0.607762	0.037*
H12B	0.270551	0.436191	0.661594	0.037*
H12C	0.152680	0.411279	0.665779	0.037*
C13	−0.02441 (11)	0.41249 (11)	0.24993 (11)	0.0234 (3)
H13A	−0.093642	0.432848	0.255975	0.035*
H13B	−0.040698	0.362349	0.195213	0.035*
H13C	0.010950	0.473390	0.235227	0.035*
C14	0.22854 (12)	0.12205 (11)	0.43677 (11)	0.0229 (3)
H14A	0.309381	0.129308	0.461515	0.034*
H14B	0.199912	0.095343	0.367747	0.034*
H14C	0.209742	0.074104	0.480178	0.034*
C15	0.57768 (11)	0.24817 (10)	0.78090 (10)	0.0179 (3)
C16	0.59395 (11)	0.31750 (10)	0.85958 (10)	0.0188 (3)
C17	0.70119 (11)	0.35298 (10)	0.91484 (10)	0.0203 (3)
H17	0.713024	0.399966	0.968560	0.024*
C18	0.79137 (11)	0.32167 (11)	0.89370 (10)	0.0210 (3)
C19	0.77190 (11)	0.25361 (11)	0.81392 (10)	0.0207 (3)
H19	0.832619	0.232259	0.798086	0.025*
C20	0.66612 (11)	0.21580 (10)	0.75651 (10)	0.0195 (3)
C21	0.49809 (11)	0.35392 (11)	0.88439 (11)	0.0228 (3)
H21A	0.523644	0.408264	0.935516	0.034*
H21B	0.469045	0.296015	0.910328	0.034*
H21C	0.439327	0.381115	0.823437	0.034*
C22	0.90777 (12)	0.35963 (12)	0.95412 (12)	0.0281 (3)
H22A	0.905297	0.414202	1.000146	0.042*
H22B	0.940177	0.386907	0.908357	0.042*
H22C	0.953302	0.302382	0.993033	0.042*
C23	0.64884 (12)	0.14485 (11)	0.66898 (11)	0.0257 (3)
H23A	0.708850	0.154847	0.645302	0.039*
H23B	0.577439	0.160375	0.614221	0.039*
H23C	0.648980	0.073193	0.690472	0.039*
C24	0.18720 (14)	0.64241 (12)	0.41048 (12)	0.0315 (4)
C25	0.29974 (13)	0.60517 (12)	0.46426 (13)	0.0313 (3)
H25A	0.329179	0.632888	0.532906	0.047*
H25B	0.346612	0.627785	0.429237	0.047*
H25C	0.299335	0.529708	0.466905	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01496 (16)	0.02198 (17)	0.02167 (17)	−0.00078 (12)	0.00560 (13)	0.00425 (13)
N1	0.0129 (5)	0.0196 (5)	0.0156 (5)	0.0005 (4)	0.0040 (4)	0.0018 (4)
N2	0.0138 (5)	0.0164 (5)	0.0214 (6)	−0.0005 (4)	0.0020 (4)	0.0038 (4)
N3	0.0424 (9)	0.0371 (8)	0.0448 (9)	−0.0020 (7)	−0.0029 (7)	0.0127 (7)
C1	0.0146 (6)	0.0160 (6)	0.0178 (6)	0.0017 (5)	0.0048 (5)	−0.0015 (5)
C2	0.0175 (6)	0.0239 (7)	0.0188 (6)	0.0016 (5)	0.0082 (5)	0.0017 (5)
C3	0.0242 (7)	0.0228 (7)	0.0299 (8)	−0.0002 (6)	0.0147 (6)	0.0050 (6)
C4	0.0241 (9)	0.0197 (8)	0.0240 (10)	0.0017 (6)	0.0109 (8)	0.0051 (7)
C5	0.0173 (7)	0.0152 (7)	0.0217 (9)	0.0016 (6)	0.0065 (6)	0.0018 (6)
C3B	0.0242 (7)	0.0228 (7)	0.0299 (8)	−0.0002 (6)	0.0147 (6)	0.0050 (6)
C4B	0.022 (4)	0.018 (4)	0.023 (4)	−0.001 (3)	0.004 (3)	0.007 (3)
C5B	0.021 (4)	0.022 (4)	0.020 (4)	0.008 (3)	0.009 (3)	0.009 (3)
C6	0.0109 (5)	0.0206 (6)	0.0156 (6)	−0.0010 (5)	0.0035 (5)	0.0020 (5)
C7	0.0134 (6)	0.0222 (6)	0.0192 (6)	−0.0006 (5)	0.0058 (5)	−0.0004 (5)
C8	0.0140 (6)	0.0204 (6)	0.0229 (7)	0.0024 (5)	0.0069 (5)	0.0021 (5)
C9	0.0125 (6)	0.0248 (7)	0.0186 (6)	−0.0009 (5)	0.0057 (5)	0.0041 (5)
C10	0.0144 (6)	0.0240 (6)	0.0166 (6)	−0.0029 (5)	0.0053 (5)	−0.0008 (5)
C11	0.0135 (6)	0.0189 (6)	0.0193 (6)	−0.0018 (5)	0.0062 (5)	0.0003 (5)
C12	0.0242 (7)	0.0247 (7)	0.0216 (7)	0.0069 (6)	0.0052 (6)	−0.0032 (6)
C13	0.0184 (6)	0.0288 (7)	0.0203 (7)	0.0027 (5)	0.0044 (5)	0.0053 (6)
C14	0.0245 (7)	0.0209 (7)	0.0216 (7)	0.0018 (5)	0.0073 (6)	−0.0018 (5)
C15	0.0136 (6)	0.0190 (6)	0.0176 (6)	−0.0006 (5)	0.0022 (5)	0.0035 (5)
C16	0.0175 (6)	0.0197 (6)	0.0184 (6)	0.0016 (5)	0.0061 (5)	0.0040 (5)
C17	0.0201 (6)	0.0217 (6)	0.0179 (6)	−0.0008 (5)	0.0062 (5)	−0.0017 (5)
C18	0.0160 (6)	0.0238 (7)	0.0204 (7)	−0.0012 (5)	0.0040 (5)	0.0010 (5)
C19	0.0148 (6)	0.0246 (7)	0.0216 (7)	0.0023 (5)	0.0058 (5)	0.0001 (5)
C20	0.0181 (6)	0.0193 (6)	0.0185 (6)	0.0023 (5)	0.0043 (5)	0.0013 (5)
C21	0.0190 (6)	0.0281 (7)	0.0225 (7)	0.0026 (5)	0.0095 (6)	0.0013 (6)
C22	0.0175 (7)	0.0341 (8)	0.0290 (8)	−0.0041 (6)	0.0053 (6)	−0.0069 (6)
C23	0.0208 (7)	0.0280 (7)	0.0245 (7)	0.0029 (6)	0.0046 (6)	−0.0061 (6)
C24	0.0391 (9)	0.0238 (7)	0.0262 (8)	−0.0071 (6)	0.0069 (7)	0.0029 (6)
C25	0.0302 (8)	0.0290 (8)	0.0348 (9)	−0.0028 (6)	0.0128 (7)	−0.0034 (7)

Geometric parameters (Å, º)

S1—C1	1.6821 (14)	C10—H10	0.9500
N1—C1	1.3627 (16)	C10—C11	1.3964 (18)
N1—C2	1.4854 (17)	C11—C14	1.5055 (18)
N1—C6	1.4448 (16)	C12—H12A	0.9800
N2—C1	1.3688 (16)	C12—H12B	0.9800
N2—C5	1.4925 (18)	C12—H12C	0.9800
N2—C5B	1.563 (9)	C13—H13A	0.9800
N2—C15	1.4456 (16)	C13—H13B	0.9800
N3—C24	1.146 (2)	C13—H13C	0.9800
C2—H2A	0.9900	C14—H14A	0.9800
C2—H2B	0.9900	C14—H14B	0.9800
C2—C3	1.5154 (19)	C14—H14C	0.9800
C2—C3B	1.5154 (19)	C15—C16	1.3980 (19)
C3—H3A	0.9900	C15—C20	1.3997 (19)
C3—H3B	0.9900	C16—C17	1.3936 (19)
C3—C4	1.545 (2)	C16—C21	1.5090 (19)
C4—H4A	0.9900	C17—H17	0.9500
C4—H4B	0.9900	C17—C18	1.390 (2)
C4—C5	1.518 (2)	C18—C19	1.393 (2)
C5—H5A	0.9900	C18—C22	1.5114 (19)
C5—H5B	0.9900	C19—H19	0.9500
C3B—H3BA	0.9900	C19—C20	1.3952 (19)
C3B—H3BB	0.9900	C20—C23	1.5068 (19)
C3B—C4B	1.467 (10)	C21—H21A	0.9800
C4B—H4BA	0.9900	C21—H21B	0.9800
C4B—H4BB	0.9900	C21—H21C	0.9800
C4B—C5B	1.485 (15)	C22—H22A	0.9800
C5B—H5BA	0.9900	C22—H22B	0.9800
C5B—H5BB	0.9900	C22—H22C	0.9800
C6—C7	1.4009 (18)	C23—H23A	0.9800
C6—C11	1.3924 (18)	C23—H23B	0.9800
C7—C8	1.3915 (18)	C23—H23C	0.9800
C7—C12	1.5074 (19)	C24—C25	1.453 (2)
C8—H8	0.9500	C25—H25A	0.9800
C8—C9	1.3934 (19)	C25—H25B	0.9800
C9—C10	1.3940 (19)	C25—H25C	0.9800
C9—C13	1.5128 (18)
C1—N1—C2	122.24 (11)	C9—C10—C11	121.56 (12)
C1—N1—C6	118.64 (11)	C11—C10—H10	119.2
C6—N1—C2	115.77 (10)	C6—C11—C10	118.46 (12)
C1—N2—C5	119.93 (11)	C6—C11—C14	121.26 (12)
C1—N2—C5B	130.4 (4)	C10—C11—C14	120.27 (12)
C1—N2—C15	119.03 (11)	C7—C12—H12A	109.5
C15—N2—C5	117.02 (11)	C7—C12—H12B	109.5
C15—N2—C5B	108.9 (4)	C7—C12—H12C	109.5
N1—C1—S1	121.91 (10)	H12A—C12—H12B	109.5
N1—C1—N2	116.20 (11)	H12A—C12—H12C	109.5
N2—C1—S1	121.89 (10)	H12B—C12—H12C	109.5
N1—C2—H2A	108.5	C9—C13—H13A	109.5
N1—C2—H2B	108.5	C9—C13—H13B	109.5
N1—C2—C3	115.28 (11)	C9—C13—H13C	109.5
N1—C2—C3B	115.28 (11)	H13A—C13—H13B	109.5
H2A—C2—H2B	107.5	H13A—C13—H13C	109.5
C3—C2—H2A	108.5	H13B—C13—H13C	109.5
C3—C2—H2B	108.5	C11—C14—H14A	109.5
C2—C3—H3A	109.5	C11—C14—H14B	109.5
C2—C3—H3B	109.5	C11—C14—H14C	109.5
C2—C3—C4	110.87 (12)	H14A—C14—H14B	109.5
H3A—C3—H3B	108.1	H14A—C14—H14C	109.5
C4—C3—H3A	109.5	H14B—C14—H14C	109.5
C4—C3—H3B	109.5	C16—C15—N2	118.23 (12)
C3—C4—H4A	109.3	C16—C15—C20	121.26 (12)
C3—C4—H4B	109.3	C20—C15—N2	120.47 (12)
H4A—C4—H4B	108.0	C15—C16—C21	121.16 (12)
C5—C4—C3	111.55 (14)	C17—C16—C15	118.47 (12)
C5—C4—H4A	109.3	C17—C16—C21	120.37 (13)
C5—C4—H4B	109.3	C16—C17—H17	119.0
N2—C5—C4	114.70 (14)	C18—C17—C16	121.96 (13)
N2—C5—H5A	108.6	C18—C17—H17	119.0
N2—C5—H5B	108.6	C17—C18—C19	118.04 (12)
C4—C5—H5A	108.6	C17—C18—C22	121.93 (13)
C4—C5—H5B	108.6	C19—C18—C22	120.03 (13)
H5A—C5—H5B	107.6	C18—C19—H19	118.9
C2—C3B—H3BA	108.9	C18—C19—C20	122.13 (13)
C2—C3B—H3BB	108.9	C20—C19—H19	118.9
H3BA—C3B—H3BB	107.8	C15—C20—C23	121.76 (12)
C4B—C3B—C2	113.2 (4)	C19—C20—C15	118.13 (13)
C4B—C3B—H3BA	108.9	C19—C20—C23	120.08 (12)
C4B—C3B—H3BB	108.9	C16—C21—H21A	109.5
C3B—C4B—H4BA	110.5	C16—C21—H21B	109.5
C3B—C4B—H4BB	110.5	C16—C21—H21C	109.5
C3B—C4B—C5B	106.3 (9)	H21A—C21—H21B	109.5
H4BA—C4B—H4BB	108.7	H21A—C21—H21C	109.5
C5B—C4B—H4BA	110.5	H21B—C21—H21C	109.5
C5B—C4B—H4BB	110.5	C18—C22—H22A	109.5
N2—C5B—H5BA	109.7	C18—C22—H22B	109.5
N2—C5B—H5BB	109.7	C18—C22—H22C	109.5
C4B—C5B—N2	110.0 (8)	H22A—C22—H22B	109.5
C4B—C5B—H5BA	109.7	H22A—C22—H22C	109.5
C4B—C5B—H5BB	109.7	H22B—C22—H22C	109.5
H5BA—C5B—H5BB	108.2	C20—C23—H23A	109.5
C7—C6—N1	119.30 (12)	C20—C23—H23B	109.5
C11—C6—N1	119.25 (11)	C20—C23—H23C	109.5
C11—C6—C7	121.45 (12)	H23A—C23—H23B	109.5
C6—C7—C12	121.49 (12)	H23A—C23—H23C	109.5
C8—C7—C6	118.34 (12)	H23B—C23—H23C	109.5
C8—C7—C12	120.13 (12)	N3—C24—C25	178.80 (19)
C7—C8—H8	119.1	C24—C25—H25A	109.5
C7—C8—C9	121.74 (12)	C24—C25—H25B	109.5
C9—C8—H8	119.1	C24—C25—H25C	109.5
C8—C9—C10	118.40 (12)	H25A—C25—H25B	109.5
C8—C9—C13	120.52 (12)	H25A—C25—H25C	109.5
C10—C9—C13	121.06 (13)	H25B—C25—H25C	109.5
C9—C10—H10	119.2
N1—C2—C3—C4	72.82 (16)	C5B—N2—C15—C20	98.3 (5)
N1—C2—C3B—C4B	37.0 (5)	C6—N1—C1—S1	9.29 (17)
N1—C6—C7—C8	−179.91 (11)	C6—N1—C1—N2	−170.76 (11)
N1—C6—C7—C12	2.12 (19)	C6—N1—C2—C3	118.47 (13)
N1—C6—C11—C10	179.67 (11)	C6—N1—C2—C3B	118.47 (13)
N1—C6—C11—C14	−0.92 (18)	C6—C7—C8—C9	−0.4 (2)
N2—C15—C16—C17	176.86 (12)	C7—C6—C11—C10	0.82 (19)
N2—C15—C16—C21	−3.40 (19)	C7—C6—C11—C14	−179.77 (12)
N2—C15—C20—C19	−176.92 (12)	C7—C8—C9—C10	2.0 (2)
N2—C15—C20—C23	5.0 (2)	C7—C8—C9—C13	−176.07 (12)
C1—N1—C2—C3	−82.51 (16)	C8—C9—C10—C11	−2.25 (19)
C1—N1—C2—C3B	−82.51 (16)	C9—C10—C11—C6	0.87 (19)
C1—N1—C6—C7	−89.84 (15)	C9—C10—C11—C14	−178.55 (12)
C1—N1—C6—C11	91.29 (15)	C11—C6—C7—C8	−1.07 (19)
C1—N2—C5—C4	−86.51 (18)	C11—C6—C7—C12	−179.03 (12)
C1—N2—C5B—C4B	38.3 (10)	C12—C7—C8—C9	177.61 (12)
C1—N2—C15—C16	87.17 (16)	C13—C9—C10—C11	175.81 (12)
C1—N2—C15—C20	−94.99 (15)	C15—N2—C1—S1	19.92 (17)
C2—N1—C1—S1	−149.15 (10)	C15—N2—C1—N1	−160.03 (12)
C2—N1—C1—N2	30.80 (17)	C15—N2—C5—C4	116.25 (15)
C2—N1—C6—C7	69.98 (15)	C15—N2—C5B—C4B	−156.9 (6)
C2—N1—C6—C11	−108.90 (13)	C15—C16—C17—C18	0.2 (2)
C2—C3—C4—C5	−58.41 (18)	C16—C15—C20—C19	0.9 (2)
C2—C3B—C4B—C5B	50.5 (8)	C16—C15—C20—C23	−177.21 (13)
C3—C4—C5—N2	70.95 (19)	C16—C17—C18—C19	0.7 (2)
C5—N2—C1—S1	−136.86 (12)	C16—C17—C18—C22	−179.58 (13)
C5—N2—C1—N1	43.19 (18)	C17—C18—C19—C20	−0.8 (2)
C5—N2—C15—C16	−115.39 (15)	C18—C19—C20—C15	0.0 (2)
C5—N2—C15—C20	62.46 (18)	C18—C19—C20—C23	178.14 (13)
C3B—C4B—C5B—N2	−88.9 (9)	C20—C15—C16—C17	−1.0 (2)
C5B—N2—C1—S1	−176.6 (6)	C20—C15—C16—C21	178.77 (12)
C5B—N2—C1—N1	3.4 (6)	C21—C16—C17—C18	−179.56 (13)
C5B—N2—C15—C16	−79.6 (5)	C22—C18—C19—C20	179.46 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···S1^i	0.99	2.92	3.6972 (17)	136
C25—H25B···S1^ii	0.98	2.92	3.8180 (17)	152

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+1.

(SDiazMesSe_MeCN)

Crystal data

C23H30N2Se·C2H3N	F(000) = 952
Mr = 454.50	Dx = 1.319 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.1365 (3) Å	Cell parameters from 9757 reflections
b = 13.3024 (2) Å	θ = 2.2–27.5°
c = 14.2478 (3) Å	µ = 1.66 mm^−1
β = 113.1557 (7)°	T = 100 K
V = 2289.18 (8) Å^3	Block, yellow
Z = 4	0.23 × 0.19 × 0.10 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	4637 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.046
φ and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −17→17
Tmin = 0.683, Tmax = 0.746	k = −17→17
40871 measured reflections	l = −18→18
5251 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.061	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0125P)^2 + 1.9573P] where P = (Fo^2 + 2Fc^2)/3
5251 reflections	(Δ/σ)max = 0.003
288 parameters	Δρmax = 0.36 e Å^−3
36 restraints	Δρmin = −0.33 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Se1	0.44339 (2)	0.35467 (2)	0.58253 (2)	0.01973 (5)
N1	0.28687 (10)	0.24512 (10)	0.62785 (9)	0.0161 (3)
N2	0.46935 (11)	0.21612 (10)	0.73881 (11)	0.0213 (3)
C1	0.39611 (13)	0.26432 (11)	0.65558 (12)	0.0172 (3)
C2	0.24099 (13)	0.20892 (12)	0.70159 (12)	0.0188 (3)
H2A	0.162063	0.228586	0.676798	0.023*
H2B	0.280551	0.242782	0.767936	0.023*
C3	0.24979 (14)	0.09602 (13)	0.71822 (14)	0.0249 (4)	0.367 (5)
H3A	0.229112	0.060344	0.652320	0.030*	0.367 (5)
H3B	0.200194	0.073442	0.751383	0.030*	0.367 (5)
C3B	0.24979 (14)	0.09602 (13)	0.71822 (14)	0.0249 (4)	0.633 (5)
H3BA	0.238342	0.079486	0.781118	0.030*	0.633 (5)
H3BB	0.190978	0.062271	0.660168	0.030*	0.633 (5)
C4	0.3775 (4)	0.0740 (3)	0.7910 (4)	0.0212 (11)	0.367 (5)
H4A	0.397775	0.113169	0.854907	0.025*	0.367 (5)
H4B	0.386508	0.001783	0.809187	0.025*	0.367 (5)
C4B	0.3613 (2)	0.0575 (2)	0.7277 (2)	0.0204 (7)	0.633 (5)
H4BA	0.363737	0.054038	0.659173	0.024*	0.633 (5)
H4BB	0.372806	−0.011230	0.756732	0.024*	0.633 (5)
C5	0.4536 (4)	0.1018 (3)	0.7391 (4)	0.0185 (11)	0.367 (5)
H5A	0.422354	0.076777	0.667898	0.022*	0.367 (5)
H5B	0.526456	0.069135	0.774958	0.022*	0.367 (5)
C5B	0.4524 (2)	0.1260 (2)	0.7958 (2)	0.0193 (7)	0.633 (5)
H5BA	0.433628	0.149539	0.852944	0.023*	0.633 (5)
H5BB	0.522381	0.087522	0.825080	0.023*	0.633 (5)
C6	0.20736 (12)	0.28483 (12)	0.53284 (11)	0.0160 (3)
C7	0.15910 (12)	0.37867 (12)	0.53314 (12)	0.0175 (3)
C8	0.08250 (12)	0.41582 (12)	0.44127 (12)	0.0187 (3)
H8	0.049180	0.479378	0.440462	0.022*
C9	0.05335 (12)	0.36221 (12)	0.35034 (12)	0.0184 (3)
C10	0.10020 (12)	0.26774 (12)	0.35358 (12)	0.0181 (3)
H10	0.078740	0.229323	0.292621	0.022*
C11	0.17782 (12)	0.22801 (12)	0.44398 (12)	0.0172 (3)
C12	0.19143 (14)	0.44013 (13)	0.62932 (12)	0.0237 (3)
H12A	0.169388	0.510262	0.611603	0.036*
H12B	0.271797	0.436567	0.667311	0.036*
H12C	0.154138	0.413551	0.671618	0.036*
C13	−0.02406 (13)	0.40737 (14)	0.25048 (12)	0.0234 (3)
H13A	−0.088689	0.435953	0.258942	0.035*
H13B	−0.048286	0.354999	0.197891	0.035*
H13C	0.014561	0.460457	0.229806	0.035*
C14	0.22918 (14)	0.12664 (12)	0.44389 (13)	0.0227 (3)
H14A	0.309892	0.133508	0.470215	0.034*
H14B	0.201674	0.100365	0.374036	0.034*
H14C	0.209353	0.080169	0.487356	0.034*
C15	0.58038 (12)	0.25532 (12)	0.78975 (12)	0.0189 (3)
C16	0.59968 (13)	0.32537 (12)	0.86766 (12)	0.0202 (3)
C17	0.70831 (14)	0.35784 (13)	0.92191 (12)	0.0221 (3)
H17	0.722717	0.404635	0.975998	0.027*
C18	0.79588 (13)	0.32364 (13)	0.89901 (13)	0.0222 (3)
C19	0.77327 (13)	0.25401 (13)	0.82044 (12)	0.0216 (3)
H19	0.832340	0.230125	0.803889	0.026*
C20	0.66649 (13)	0.21832 (12)	0.76533 (12)	0.0211 (3)
C21	0.50612 (14)	0.36652 (14)	0.89236 (13)	0.0256 (4)
H21A	0.534310	0.419661	0.943789	0.038*
H21B	0.474426	0.312396	0.919020	0.038*
H21C	0.448837	0.394234	0.830324	0.038*
C22	0.91285 (14)	0.36019 (15)	0.95683 (14)	0.0300 (4)
H22A	0.912669	0.414434	1.003306	0.045*
H22B	0.943119	0.385324	0.908463	0.045*
H22C	0.958675	0.304515	0.996261	0.045*
C23	0.64518 (15)	0.14426 (14)	0.67956 (14)	0.0312 (4)
H23A	0.710600	0.140119	0.662776	0.047*
H23B	0.581416	0.166603	0.619380	0.047*
H23C	0.629677	0.077905	0.700787	0.047*
N3	0.07928 (16)	0.66649 (14)	0.36865 (15)	0.0471 (5)
C24	0.17011 (17)	0.64243 (14)	0.40537 (14)	0.0313 (4)
C25	0.28509 (16)	0.61080 (15)	0.45398 (16)	0.0335 (4)
H25A	0.320731	0.645878	0.519306	0.050*
H25B	0.323767	0.627122	0.409489	0.050*
H25C	0.288256	0.538100	0.465909	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.01439 (8)	0.02322 (9)	0.02095 (8)	−0.00069 (6)	0.00629 (6)	0.00366 (6)
N1	0.0141 (6)	0.0181 (6)	0.0157 (6)	0.0007 (5)	0.0055 (5)	0.0013 (5)
N2	0.0135 (6)	0.0189 (7)	0.0270 (7)	−0.0004 (5)	0.0031 (5)	0.0073 (6)
C1	0.0158 (7)	0.0155 (7)	0.0190 (7)	0.0007 (6)	0.0054 (6)	−0.0023 (6)
C2	0.0172 (7)	0.0222 (8)	0.0184 (7)	0.0017 (6)	0.0087 (6)	0.0013 (6)
C3	0.0246 (8)	0.0247 (9)	0.0299 (9)	0.0001 (7)	0.0154 (7)	0.0061 (7)
C3B	0.0246 (8)	0.0247 (9)	0.0299 (9)	0.0001 (7)	0.0154 (7)	0.0061 (7)
C4	0.021 (2)	0.020 (2)	0.024 (3)	0.0033 (17)	0.0091 (18)	0.0034 (18)
C4B	0.0218 (13)	0.0167 (12)	0.0204 (15)	−0.0024 (10)	0.0059 (11)	−0.0001 (10)
C5	0.018 (2)	0.015 (2)	0.020 (2)	−0.0002 (16)	0.0058 (17)	−0.0003 (17)
C5B	0.0209 (12)	0.0165 (13)	0.0176 (14)	0.0005 (10)	0.0046 (10)	0.0041 (10)
C6	0.0113 (7)	0.0198 (7)	0.0162 (7)	−0.0001 (6)	0.0049 (6)	0.0022 (6)
C7	0.0135 (7)	0.0196 (8)	0.0194 (7)	−0.0008 (6)	0.0064 (6)	−0.0007 (6)
C8	0.0140 (7)	0.0208 (8)	0.0219 (8)	0.0022 (6)	0.0075 (6)	0.0020 (6)
C9	0.0129 (7)	0.0247 (8)	0.0178 (7)	−0.0008 (6)	0.0063 (6)	0.0026 (6)
C10	0.0154 (7)	0.0231 (8)	0.0161 (7)	−0.0039 (6)	0.0064 (6)	−0.0014 (6)
C11	0.0140 (7)	0.0192 (7)	0.0195 (7)	−0.0014 (6)	0.0080 (6)	0.0001 (6)
C12	0.0212 (8)	0.0241 (8)	0.0220 (8)	0.0059 (7)	0.0043 (7)	−0.0035 (7)
C13	0.0179 (8)	0.0305 (9)	0.0199 (8)	0.0021 (7)	0.0055 (6)	0.0034 (7)
C14	0.0249 (8)	0.0220 (8)	0.0202 (8)	0.0031 (7)	0.0077 (7)	−0.0001 (6)
C15	0.0136 (7)	0.0204 (8)	0.0195 (7)	0.0000 (6)	0.0032 (6)	0.0059 (6)
C16	0.0188 (8)	0.0229 (8)	0.0198 (7)	0.0024 (6)	0.0086 (6)	0.0059 (6)
C17	0.0223 (8)	0.0249 (8)	0.0185 (7)	−0.0004 (7)	0.0073 (6)	−0.0024 (6)
C18	0.0172 (8)	0.0253 (8)	0.0218 (8)	−0.0018 (6)	0.0053 (6)	0.0005 (7)
C19	0.0152 (7)	0.0262 (9)	0.0220 (8)	0.0025 (6)	0.0059 (6)	−0.0006 (7)
C20	0.0189 (8)	0.0196 (8)	0.0205 (8)	0.0022 (6)	0.0031 (6)	0.0001 (6)
C21	0.0210 (8)	0.0323 (10)	0.0248 (8)	0.0053 (7)	0.0104 (7)	0.0034 (7)
C22	0.0189 (8)	0.0383 (10)	0.0304 (9)	−0.0067 (7)	0.0071 (7)	−0.0074 (8)
C23	0.0230 (9)	0.0303 (10)	0.0308 (9)	0.0054 (7)	0.0005 (7)	−0.0105 (8)
N3	0.0389 (10)	0.0387 (10)	0.0461 (11)	−0.0018 (8)	−0.0021 (9)	0.0150 (8)
C24	0.0371 (11)	0.0256 (9)	0.0256 (9)	−0.0068 (8)	0.0063 (8)	0.0043 (7)
C25	0.0295 (10)	0.0319 (10)	0.0390 (11)	−0.0058 (8)	0.0132 (8)	−0.0060 (8)

Geometric parameters (Å, º)

Se1—C1	1.8498 (16)	C10—C11	1.395 (2)
N1—C1	1.355 (2)	C11—C14	1.508 (2)
N1—C2	1.482 (2)	C12—H12A	0.9800
N1—C6	1.4458 (19)	C12—H12B	0.9800
N2—C1	1.359 (2)	C12—H12C	0.9800
N2—C5	1.535 (5)	C13—H13A	0.9800
N2—C5B	1.512 (3)	C13—H13B	0.9800
N2—C15	1.4469 (19)	C13—H13C	0.9800
C2—H2A	0.9900	C14—H14A	0.9800
C2—H2B	0.9900	C14—H14B	0.9800
C2—C3	1.518 (2)	C14—H14C	0.9800
C2—C3B	1.518 (2)	C15—C16	1.394 (2)
C3—H3A	0.9900	C15—C20	1.397 (2)
C3—H3B	0.9900	C16—C17	1.397 (2)
C3—C4	1.614 (5)	C16—C21	1.508 (2)
C3B—H3BA	0.9900	C17—H17	0.9500
C3B—H3BB	0.9900	C17—C18	1.390 (2)
C3B—C4B	1.507 (3)	C18—C19	1.392 (2)
C4—H4A	0.9900	C18—C22	1.510 (2)
C4—H4B	0.9900	C19—H19	0.9500
C4—C5	1.506 (7)	C19—C20	1.394 (2)
C4B—H4BA	0.9900	C20—C23	1.508 (2)
C4B—H4BB	0.9900	C21—H21A	0.9800
C4B—C5B	1.514 (4)	C21—H21B	0.9800
C5—H5A	0.9900	C21—H21C	0.9800
C5—H5B	0.9900	C22—H22A	0.9800
C5B—H5BA	0.9900	C22—H22B	0.9800
C5B—H5BB	0.9900	C22—H22C	0.9800
C6—C7	1.401 (2)	C23—H23A	0.9800
C6—C11	1.392 (2)	C23—H23B	0.9800
C7—C8	1.391 (2)	C23—H23C	0.9800
C7—C12	1.506 (2)	N3—C24	1.144 (3)
C8—H8	0.9500	C24—C25	1.455 (3)
C8—C9	1.394 (2)	C25—H25A	0.9800
C9—C10	1.392 (2)	C25—H25B	0.9800
C9—C13	1.510 (2)	C25—H25C	0.9800
C10—H10	0.9500
C1—N1—C2	122.27 (13)	C9—C10—C11	121.73 (15)
C1—N1—C6	119.78 (13)	C11—C10—H10	119.1
C6—N1—C2	115.91 (12)	C6—C11—C10	118.38 (14)
C1—N2—C5	114.8 (2)	C6—C11—C14	121.42 (14)
C1—N2—C5B	129.74 (15)	C10—C11—C14	120.19 (14)
C1—N2—C15	119.73 (13)	C7—C12—H12A	109.5
C15—N2—C5	117.8 (2)	C7—C12—H12B	109.5
C15—N2—C5B	110.40 (14)	C7—C12—H12C	109.5
N1—C1—Se1	120.66 (11)	H12A—C12—H12B	109.5
N1—C1—N2	118.10 (14)	H12A—C12—H12C	109.5
N2—C1—Se1	121.23 (12)	H12B—C12—H12C	109.5
N1—C2—H2A	108.8	C9—C13—H13A	109.5
N1—C2—H2B	108.8	C9—C13—H13B	109.5
N1—C2—C3	113.88 (13)	C9—C13—H13C	109.5
N1—C2—C3B	113.88 (13)	H13A—C13—H13B	109.5
H2A—C2—H2B	107.7	H13A—C13—H13C	109.5
C3—C2—H2A	108.8	H13B—C13—H13C	109.5
C3—C2—H2B	108.8	C11—C14—H14A	109.5
C2—C3—H3A	110.5	C11—C14—H14B	109.5
C2—C3—H3B	110.5	C11—C14—H14C	109.5
C2—C3—C4	106.0 (2)	H14A—C14—H14B	109.5
H3A—C3—H3B	108.7	H14A—C14—H14C	109.5
C4—C3—H3A	110.5	H14B—C14—H14C	109.5
C4—C3—H3B	110.5	C16—C15—N2	118.18 (15)
C2—C3B—H3BA	109.4	C16—C15—C20	121.48 (14)
C2—C3B—H3BB	109.4	C20—C15—N2	120.21 (15)
H3BA—C3B—H3BB	108.0	C15—C16—C17	118.26 (15)
C4B—C3B—C2	111.26 (16)	C15—C16—C21	121.24 (15)
C4B—C3B—H3BA	109.4	C17—C16—C21	120.50 (15)
C4B—C3B—H3BB	109.4	C16—C17—H17	119.1
C3—C4—H4A	109.4	C18—C17—C16	121.90 (16)
C3—C4—H4B	109.4	C18—C17—H17	119.1
H4A—C4—H4B	108.0	C17—C18—C19	118.17 (15)
C5—C4—C3	111.3 (4)	C17—C18—C22	121.67 (16)
C5—C4—H4A	109.4	C19—C18—C22	120.16 (16)
C5—C4—H4B	109.4	C18—C19—H19	119.0
C3B—C4B—H4BA	109.6	C18—C19—C20	121.92 (16)
C3B—C4B—H4BB	109.6	C20—C19—H19	119.0
C3B—C4B—C5B	110.3 (2)	C15—C20—C23	121.44 (15)
H4BA—C4B—H4BB	108.1	C19—C20—C15	118.26 (15)
C5B—C4B—H4BA	109.6	C19—C20—C23	120.27 (15)
C5B—C4B—H4BB	109.6	C16—C21—H21A	109.5
N2—C5—H5A	109.4	C16—C21—H21B	109.5
N2—C5—H5B	109.4	C16—C21—H21C	109.5
C4—C5—N2	111.1 (4)	H21A—C21—H21B	109.5
C4—C5—H5A	109.4	H21A—C21—H21C	109.5
C4—C5—H5B	109.4	H21B—C21—H21C	109.5
H5A—C5—H5B	108.0	C18—C22—H22A	109.5
N2—C5B—C4B	112.3 (2)	C18—C22—H22B	109.5
N2—C5B—H5BA	109.1	C18—C22—H22C	109.5
N2—C5B—H5BB	109.1	H22A—C22—H22B	109.5
C4B—C5B—H5BA	109.1	H22A—C22—H22C	109.5
C4B—C5B—H5BB	109.1	H22B—C22—H22C	109.5
H5BA—C5B—H5BB	107.9	C20—C23—H23A	109.5
C7—C6—N1	118.94 (14)	C20—C23—H23B	109.5
C11—C6—N1	119.57 (14)	C20—C23—H23C	109.5
C11—C6—C7	121.46 (14)	H23A—C23—H23B	109.5
C6—C7—C12	121.36 (14)	H23A—C23—H23C	109.5
C8—C7—C6	118.34 (14)	H23B—C23—H23C	109.5
C8—C7—C12	120.27 (14)	N3—C24—C25	178.7 (2)
C7—C8—H8	119.2	C24—C25—H25A	109.5
C7—C8—C9	121.70 (15)	C24—C25—H25B	109.5
C9—C8—H8	119.2	C24—C25—H25C	109.5
C8—C9—C13	120.60 (15)	H25A—C25—H25B	109.5
C10—C9—C8	118.34 (14)	H25A—C25—H25C	109.5
C10—C9—C13	121.03 (15)	H25B—C25—H25C	109.5
C9—C10—H10	119.1
N1—C2—C3—C4	76.4 (2)	C5B—N2—C15—C20	88.8 (2)
N1—C2—C3B—C4B	42.9 (2)	C6—N1—C1—Se1	8.35 (19)
N1—C6—C7—C8	−179.80 (14)	C6—N1—C1—N2	−172.24 (14)
N1—C6—C7—C12	2.2 (2)	C6—N1—C2—C3	112.40 (15)
N1—C6—C11—C10	179.43 (14)	C6—N1—C2—C3B	112.40 (15)
N1—C6—C11—C14	−1.6 (2)	C6—C7—C8—C9	0.0 (2)
N2—C15—C16—C17	175.44 (14)	C7—C6—C11—C10	1.5 (2)
N2—C15—C16—C21	−5.4 (2)	C7—C6—C11—C14	−179.52 (15)
N2—C15—C20—C19	−176.33 (14)	C7—C8—C9—C10	2.1 (2)
N2—C15—C20—C23	5.6 (2)	C7—C8—C9—C13	−175.77 (15)
C1—N1—C2—C3	−83.91 (18)	C8—C9—C10—C11	−2.5 (2)
C1—N1—C2—C3B	−83.91 (18)	C9—C10—C11—C6	0.7 (2)
C1—N1—C6—C7	−91.48 (18)	C9—C10—C11—C14	−178.26 (15)
C1—N1—C6—C11	90.54 (18)	C11—C6—C7—C8	−1.9 (2)
C1—N2—C5—C4	−90.9 (4)	C11—C6—C7—C12	−179.83 (15)
C1—N2—C5B—C4B	28.1 (4)	C12—C7—C8—C9	177.99 (15)
C1—N2—C15—C16	89.25 (19)	C13—C9—C10—C11	175.38 (14)
C1—N2—C15—C20	−94.90 (19)	C15—N2—C1—Se1	18.5 (2)
C2—N1—C1—Se1	−154.72 (12)	C15—N2—C1—N1	−160.95 (14)
C2—N1—C1—N2	24.7 (2)	C15—N2—C5—C4	119.6 (3)
C2—N1—C6—C7	72.64 (18)	C15—N2—C5B—C4B	−156.2 (2)
C2—N1—C6—C11	−105.35 (16)	C15—C16—C17—C18	1.1 (2)
C2—C3—C4—C5	−63.8 (4)	C16—C15—C20—C19	−0.6 (2)
C2—C3B—C4B—C5B	43.9 (3)	C16—C15—C20—C23	−178.66 (16)
C3—C4—C5—N2	76.3 (5)	C16—C17—C18—C19	−0.9 (3)
C3B—C4B—C5B—N2	−82.9 (3)	C16—C17—C18—C22	179.05 (16)
C5—N2—C1—Se1	−130.4 (2)	C17—C18—C19—C20	−0.1 (3)
C5—N2—C1—N1	50.2 (3)	C18—C19—C20—C15	0.9 (3)
C5—N2—C15—C16	−122.8 (3)	C18—C19—C20—C23	178.94 (16)
C5—N2—C15—C20	53.0 (3)	C20—C15—C16—C17	−0.4 (2)
C5B—N2—C1—Se1	−166.11 (19)	C20—C15—C16—C21	178.83 (15)
C5B—N2—C1—N1	14.5 (3)	C21—C16—C17—C18	−178.05 (16)
C5B—N2—C15—C16	−87.0 (2)	C22—C18—C19—C20	179.91 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···Se1^i	0.99	3.09	4.009 (6)	155
C4—H4B···Se1^ii	0.99	2.91	3.737 (4)	141
C4B—H4BB···Se1^ii	0.99	3.15	3.965 (3)	141
C25—H25B···Se1^iii	0.98	3.03	3.829 (2)	140

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+1, −y+1, −z+1.

(SDiazMesSI2)

Crystal data

C23H30I2N2S	Z = 2
Mr = 620.35	F(000) = 608
Triclinic, P1	Dx = 1.694 Mg m^−3
a = 7.9505 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.5048 (4) Å	Cell parameters from 9861 reflections
c = 18.2812 (9) Å	θ = 2.3–27.3°
α = 81.040 (3)°	µ = 2.68 mm^−1
β = 89.926 (2)°	T = 100 K
γ = 85.125 (2)°	Plate, red
V = 1216.54 (10) Å^3	0.17 × 0.12 × 0.08 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	4834 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.067
φ and ω scans	θmax = 27.4°, θmin = 2.4°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −10→10
Tmin = 0.636, Tmax = 0.746	k = −10→10
37544 measured reflections	l = −23→23
5455 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.072	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0141P)^2 + 2.7069P] where P = (Fo^2 + 2Fc^2)/3
5455 reflections	(Δ/σ)max = 0.001
259 parameters	Δρmax = 1.35 e Å^−3
0 restraints	Δρmin = −1.40 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.28705 (3)	0.88440 (3)	0.22530 (2)	0.01492 (7)
I2	0.06264 (3)	1.09545 (3)	0.12352 (2)	0.02728 (8)
S1	0.47932 (10)	0.66975 (11)	0.31875 (5)	0.01703 (18)
N1	0.8088 (3)	0.6376 (3)	0.33943 (15)	0.0127 (6)
N2	0.7225 (3)	0.6387 (3)	0.21680 (15)	0.0130 (6)
C1	0.6852 (4)	0.6480 (4)	0.28741 (19)	0.0134 (7)
C2	0.9843 (4)	0.5614 (4)	0.3374 (2)	0.0168 (7)
H2A	1.018107	0.509455	0.388167	0.020*
H2B	1.061092	0.645979	0.322132	0.020*
C3	1.0080 (5)	0.4375 (5)	0.2856 (2)	0.0213 (8)
H3A	1.114530	0.370121	0.298913	0.026*
H3B	0.914180	0.367398	0.292614	0.026*
C4	1.0133 (4)	0.5118 (5)	0.2043 (2)	0.0196 (8)
H4A	1.129903	0.537851	0.191607	0.024*
H4B	0.981390	0.433713	0.173079	0.024*
C5	0.8946 (4)	0.6622 (4)	0.18810 (19)	0.0158 (7)
H5A	0.941171	0.747917	0.210723	0.019*
H5B	0.887569	0.697375	0.133882	0.019*
C6	0.7742 (4)	0.7057 (4)	0.40671 (18)	0.0139 (7)
C7	0.7426 (4)	0.6058 (4)	0.47232 (19)	0.0159 (7)
C8	0.7116 (4)	0.6771 (5)	0.53581 (19)	0.0179 (7)
H8	0.686611	0.611912	0.580889	0.021*
C9	0.7166 (5)	0.8403 (5)	0.5346 (2)	0.0207 (8)
C10	0.7539 (5)	0.9335 (5)	0.4683 (2)	0.0208 (8)
H10	0.760278	1.044830	0.467324	0.025*
C11	0.7822 (4)	0.8702 (4)	0.4034 (2)	0.0168 (7)
C12	0.7344 (5)	0.4291 (4)	0.4761 (2)	0.0220 (8)
H12A	0.687198	0.407252	0.429589	0.033*
H12B	0.662310	0.389509	0.517285	0.033*
H12C	0.848221	0.375011	0.483966	0.033*
C13	0.6858 (6)	0.9149 (5)	0.6037 (2)	0.0301 (9)
H13A	0.793836	0.936811	0.623955	0.045*
H13B	0.629485	0.841323	0.640475	0.045*
H13C	0.613919	1.015073	0.591360	0.045*
C14	0.8136 (5)	0.9761 (5)	0.3316 (2)	0.0244 (8)
H14A	0.920452	0.938395	0.310805	0.037*
H14B	0.819568	1.086062	0.340714	0.037*
H14C	0.721199	0.972794	0.296618	0.037*
C15	0.5972 (4)	0.6111 (4)	0.16372 (18)	0.0128 (7)
C16	0.5322 (4)	0.4619 (4)	0.16910 (19)	0.0144 (7)
C17	0.4114 (4)	0.4417 (4)	0.11705 (19)	0.0150 (7)
H17	0.365081	0.341456	0.120577	0.018*
C18	0.3563 (4)	0.5630 (5)	0.0602 (2)	0.0185 (7)
C19	0.4284 (4)	0.7073 (4)	0.05493 (19)	0.0173 (7)
H19	0.394263	0.790240	0.015399	0.021*
C20	0.5490 (4)	0.7349 (4)	0.10561 (19)	0.0154 (7)
C21	0.5925 (5)	0.3234 (4)	0.2275 (2)	0.0197 (7)
H21A	0.522420	0.234631	0.225713	0.030*
H21B	0.584081	0.356488	0.276435	0.030*
H21C	0.710358	0.288864	0.218221	0.030*
C22	0.2198 (4)	0.5396 (5)	0.0072 (2)	0.0219 (8)
H22A	0.194199	0.427520	0.015651	0.033*
H22B	0.258125	0.567836	−0.043793	0.033*
H22C	0.118065	0.608065	0.015052	0.033*
C23	0.6172 (5)	0.8963 (4)	0.0964 (2)	0.0204 (8)
H23A	0.665570	0.912993	0.143618	0.031*
H23B	0.525513	0.979378	0.081082	0.031*
H23C	0.704890	0.901765	0.058623	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01112 (11)	0.01644 (12)	0.01866 (12)	−0.00050 (8)	0.00204 (8)	−0.00765 (9)
I2	0.02175 (13)	0.01754 (13)	0.03991 (17)	0.00034 (10)	−0.00680 (11)	0.00272 (11)
S1	0.0101 (4)	0.0260 (5)	0.0145 (4)	0.0008 (3)	0.0011 (3)	−0.0028 (4)
N1	0.0117 (13)	0.0123 (14)	0.0134 (14)	0.0019 (11)	0.0013 (10)	−0.0015 (11)
N2	0.0102 (13)	0.0167 (15)	0.0129 (14)	−0.0022 (11)	0.0026 (10)	−0.0039 (11)
C1	0.0127 (15)	0.0128 (16)	0.0150 (16)	0.0002 (12)	0.0018 (12)	−0.0035 (13)
C2	0.0105 (15)	0.0200 (18)	0.0193 (18)	0.0027 (13)	−0.0015 (13)	−0.0035 (14)
C3	0.0172 (17)	0.0200 (19)	0.026 (2)	0.0055 (14)	−0.0001 (14)	−0.0046 (16)
C4	0.0116 (16)	0.023 (2)	0.0254 (19)	0.0040 (14)	0.0029 (14)	−0.0103 (16)
C5	0.0084 (15)	0.0220 (19)	0.0171 (17)	−0.0031 (13)	0.0049 (12)	−0.0023 (14)
C6	0.0106 (15)	0.0165 (18)	0.0143 (16)	0.0030 (13)	−0.0024 (12)	−0.0039 (14)
C7	0.0125 (15)	0.0174 (18)	0.0172 (17)	0.0005 (13)	−0.0023 (13)	−0.0022 (14)
C8	0.0162 (16)	0.0224 (19)	0.0130 (16)	0.0017 (14)	0.0005 (13)	0.0016 (14)
C9	0.0208 (18)	0.024 (2)	0.0184 (18)	0.0040 (15)	−0.0034 (14)	−0.0098 (15)
C10	0.0250 (18)	0.0154 (18)	0.0232 (19)	0.0015 (14)	−0.0003 (15)	−0.0084 (15)
C11	0.0143 (16)	0.0163 (18)	0.0198 (18)	0.0015 (13)	0.0004 (13)	−0.0043 (14)
C12	0.0261 (19)	0.0162 (19)	0.024 (2)	−0.0016 (15)	0.0023 (15)	−0.0035 (15)
C13	0.037 (2)	0.035 (2)	0.019 (2)	0.0080 (19)	−0.0023 (17)	−0.0148 (18)
C14	0.033 (2)	0.017 (2)	0.023 (2)	−0.0012 (16)	0.0029 (16)	−0.0035 (16)
C15	0.0097 (14)	0.0182 (17)	0.0110 (15)	−0.0011 (13)	0.0020 (12)	−0.0042 (13)
C16	0.0145 (16)	0.0129 (17)	0.0157 (16)	0.0011 (13)	0.0042 (13)	−0.0031 (13)
C17	0.0099 (15)	0.0188 (18)	0.0188 (17)	−0.0010 (13)	0.0052 (13)	−0.0105 (14)
C18	0.0108 (15)	0.030 (2)	0.0164 (17)	0.0016 (14)	0.0037 (13)	−0.0099 (15)
C19	0.0177 (16)	0.0196 (18)	0.0129 (16)	0.0047 (14)	0.0007 (13)	−0.0006 (14)
C20	0.0161 (16)	0.0148 (17)	0.0152 (17)	−0.0001 (13)	0.0037 (13)	−0.0028 (14)
C21	0.0192 (17)	0.0149 (18)	0.0244 (19)	−0.0013 (14)	−0.0011 (14)	−0.0011 (15)
C22	0.0167 (17)	0.030 (2)	0.0205 (19)	−0.0012 (15)	−0.0009 (14)	−0.0074 (16)
C23	0.0212 (18)	0.0188 (19)	0.0205 (19)	−0.0003 (14)	0.0026 (14)	−0.0015 (15)

Geometric parameters (Å, º)

I1—I2	2.8794 (4)	C11—C14	1.505 (5)
I1—S1	2.6738 (9)	C12—H12A	0.9800
S1—C1	1.738 (3)	C12—H12B	0.9800
N1—C1	1.356 (4)	C12—H12C	0.9800
N1—C2	1.491 (4)	C13—H13A	0.9800
N1—C6	1.455 (4)	C13—H13B	0.9800
N2—C1	1.337 (4)	C13—H13C	0.9800
N2—C5	1.483 (4)	C14—H14A	0.9800
N2—C15	1.449 (4)	C14—H14B	0.9800
C2—H2A	0.9900	C14—H14C	0.9800
C2—H2B	0.9900	C15—C16	1.400 (5)
C2—C3	1.524 (5)	C15—C20	1.402 (5)
C3—H3A	0.9900	C16—C17	1.393 (5)
C3—H3B	0.9900	C16—C21	1.507 (5)
C3—C4	1.523 (5)	C17—H17	0.9500
C4—H4A	0.9900	C17—C18	1.388 (5)
C4—H4B	0.9900	C18—C19	1.389 (5)
C4—C5	1.514 (5)	C18—C22	1.502 (5)
C5—H5A	0.9900	C19—H19	0.9500
C5—H5B	0.9900	C19—C20	1.393 (5)
C6—C7	1.393 (5)	C20—C23	1.504 (5)
C6—C11	1.398 (5)	C21—H21A	0.9800
C7—C8	1.403 (5)	C21—H21B	0.9800
C7—C12	1.501 (5)	C21—H21C	0.9800
C8—H8	0.9500	C22—H22A	0.9800
C8—C9	1.388 (5)	C22—H22B	0.9800
C9—C10	1.388 (5)	C22—H22C	0.9800
C9—C13	1.509 (5)	C23—H23A	0.9800
C10—H10	0.9500	C23—H23B	0.9800
C10—C11	1.388 (5)	C23—H23C	0.9800
S1—I1—I2	175.38 (2)	C7—C12—H12B	109.5
C1—S1—I1	111.45 (12)	C7—C12—H12C	109.5
C1—N1—C2	127.7 (3)	H12A—C12—H12B	109.5
C1—N1—C6	119.4 (3)	H12A—C12—H12C	109.5
C6—N1—C2	112.9 (3)	H12B—C12—H12C	109.5
C1—N2—C5	121.2 (3)	C9—C13—H13A	109.5
C1—N2—C15	122.3 (3)	C9—C13—H13B	109.5
C15—N2—C5	116.4 (3)	C9—C13—H13C	109.5
N1—C1—S1	116.0 (2)	H13A—C13—H13B	109.5
N2—C1—S1	123.0 (2)	H13A—C13—H13C	109.5
N2—C1—N1	121.0 (3)	H13B—C13—H13C	109.5
N1—C2—H2A	108.6	C11—C14—H14A	109.5
N1—C2—H2B	108.6	C11—C14—H14B	109.5
N1—C2—C3	114.6 (3)	C11—C14—H14C	109.5
H2A—C2—H2B	107.6	H14A—C14—H14B	109.5
C3—C2—H2A	108.6	H14A—C14—H14C	109.5
C3—C2—H2B	108.6	H14B—C14—H14C	109.5
C2—C3—H3A	109.0	C16—C15—N2	120.3 (3)
C2—C3—H3B	109.0	C16—C15—C20	121.3 (3)
H3A—C3—H3B	107.8	C20—C15—N2	118.4 (3)
C4—C3—C2	113.0 (3)	C15—C16—C21	122.2 (3)
C4—C3—H3A	109.0	C17—C16—C15	118.1 (3)
C4—C3—H3B	109.0	C17—C16—C21	119.7 (3)
C3—C4—H4A	109.4	C16—C17—H17	118.9
C3—C4—H4B	109.4	C18—C17—C16	122.3 (3)
H4A—C4—H4B	108.0	C18—C17—H17	118.9
C5—C4—C3	111.4 (3)	C17—C18—C19	118.0 (3)
C5—C4—H4A	109.4	C17—C18—C22	120.8 (3)
C5—C4—H4B	109.4	C19—C18—C22	121.2 (3)
N2—C5—C4	112.6 (3)	C18—C19—H19	118.8
N2—C5—H5A	109.1	C18—C19—C20	122.3 (3)
N2—C5—H5B	109.1	C20—C19—H19	118.8
C4—C5—H5A	109.1	C15—C20—C23	123.5 (3)
C4—C5—H5B	109.1	C19—C20—C15	117.9 (3)
H5A—C5—H5B	107.8	C19—C20—C23	118.5 (3)
C7—C6—N1	119.7 (3)	C16—C21—H21A	109.5
C7—C6—C11	122.3 (3)	C16—C21—H21B	109.5
C11—C6—N1	117.9 (3)	C16—C21—H21C	109.5
C6—C7—C8	117.5 (3)	H21A—C21—H21B	109.5
C6—C7—C12	122.5 (3)	H21A—C21—H21C	109.5
C8—C7—C12	120.0 (3)	H21B—C21—H21C	109.5
C7—C8—H8	119.1	C18—C22—H22A	109.5
C9—C8—C7	121.9 (3)	C18—C22—H22B	109.5
C9—C8—H8	119.1	C18—C22—H22C	109.5
C8—C9—C10	118.2 (3)	H22A—C22—H22B	109.5
C8—C9—C13	121.3 (4)	H22A—C22—H22C	109.5
C10—C9—C13	120.5 (4)	H22B—C22—H22C	109.5
C9—C10—H10	118.7	C20—C23—H23A	109.5
C11—C10—C9	122.5 (3)	C20—C23—H23B	109.5
C11—C10—H10	118.7	C20—C23—H23C	109.5
C6—C11—C14	121.4 (3)	H23A—C23—H23B	109.5
C10—C11—C6	117.5 (3)	H23A—C23—H23C	109.5
C10—C11—C14	121.1 (3)	H23B—C23—H23C	109.5
C7—C12—H12A	109.5
I1—S1—C1—N1	137.9 (2)	C6—N1—C2—C3	158.0 (3)
I1—S1—C1—N2	−43.2 (3)	C6—C7—C8—C9	−1.8 (5)
N1—C2—C3—C4	76.3 (4)	C7—C6—C11—C10	−1.3 (5)
N1—C6—C7—C8	179.3 (3)	C7—C6—C11—C14	−178.9 (3)
N1—C6—C7—C12	−3.0 (5)	C7—C8—C9—C10	−0.2 (5)
N1—C6—C11—C10	−178.2 (3)	C7—C8—C9—C13	−179.0 (3)
N1—C6—C11—C14	4.2 (5)	C8—C9—C10—C11	1.5 (5)
N2—C15—C16—C17	179.6 (3)	C9—C10—C11—C6	−0.8 (5)
N2—C15—C16—C21	−2.2 (5)	C9—C10—C11—C14	176.8 (4)
N2—C15—C20—C19	−179.9 (3)	C11—C6—C7—C8	2.6 (5)
N2—C15—C20—C23	−1.6 (5)	C11—C6—C7—C12	−179.8 (3)
C1—N1—C2—C3	−21.6 (5)	C12—C7—C8—C9	−179.5 (3)
C1—N1—C6—C7	102.1 (4)	C13—C9—C10—C11	−179.6 (3)
C1—N1—C6—C11	−81.0 (4)	C15—N2—C1—S1	−13.8 (5)
C1—N2—C5—C4	83.1 (4)	C15—N2—C1—N1	165.0 (3)
C1—N2—C15—C16	−70.4 (4)	C15—N2—C5—C4	−99.0 (3)
C1—N2—C15—C20	112.3 (4)	C15—C16—C17—C18	0.9 (5)
C2—N1—C1—S1	155.4 (3)	C16—C15—C20—C19	2.8 (5)
C2—N1—C1—N2	−23.4 (5)	C16—C15—C20—C23	−178.9 (3)
C2—N1—C6—C7	−77.6 (4)	C16—C17—C18—C19	1.5 (5)
C2—N1—C6—C11	99.3 (3)	C16—C17—C18—C22	−177.1 (3)
C2—C3—C4—C5	−35.7 (4)	C17—C18—C19—C20	−1.8 (5)
C3—C4—C5—N2	−49.8 (4)	C18—C19—C20—C15	−0.2 (5)
C5—N2—C1—S1	164.0 (3)	C18—C19—C20—C23	−178.6 (3)
C5—N2—C1—N1	−17.2 (5)	C20—C15—C16—C17	−3.1 (5)
C5—N2—C15—C16	111.8 (3)	C20—C15—C16—C21	175.0 (3)
C5—N2—C15—C20	−65.6 (4)	C21—C16—C17—C18	−177.2 (3)
C6—N1—C1—S1	−24.2 (4)	C22—C18—C19—C20	176.7 (3)
C6—N1—C1—N2	157.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···I1^i	0.99	3.16	4.111 (4)	162
C4—H4B···I2^ii	0.99	3.16	4.034 (4)	148
C5—H5A···I1^i	0.99	3.10	3.896 (3)	138

Symmetry codes: (i) x+1, y, z; (ii) x+1, y−1, z.

(SDiazMesSeI2)

Crystal data

C23H30I2N2Se	Z = 2
Mr = 667.25	F(000) = 644
Triclinic, P1	Dx = 1.809 Mg m^−3
a = 8.0282 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.4305 (8) Å	Cell parameters from 9806 reflections
c = 18.3525 (16) Å	θ = 2.5–30.6°
α = 81.814 (4)°	µ = 4.06 mm^−1
β = 89.706 (4)°	T = 100 K
γ = 85.171 (4)°	Block, red
V = 1225.08 (18) Å^3	0.19 × 0.15 × 0.13 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	6504 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.045
φ and ω scans	θmax = 30.6°, θmin = 2.2°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −11→11
Tmin = 0.634, Tmax = 0.746	k = −12→12
53696 measured reflections	l = −26→26
7479 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.049	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0078P)^2 + 1.5207P] where P = (Fo^2 + 2Fc^2)/3
7479 reflections	(Δ/σ)max = 0.002
259 parameters	Δρmax = 0.70 e Å^−3
0 restraints	Δρmin = −0.75 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.27703 (2)	0.89168 (2)	0.22239 (2)	0.01494 (3)
I2	0.05678 (2)	1.09633 (2)	0.11610 (2)	0.02769 (4)
Se1	0.46782 (2)	0.67455 (3)	0.32117 (2)	0.01656 (5)
N1	0.7225 (2)	0.6396 (2)	0.21435 (9)	0.0130 (3)
N2	0.8114 (2)	0.6379 (2)	0.33598 (9)	0.0135 (3)
C1	0.6888 (2)	0.6496 (2)	0.28490 (10)	0.0126 (3)
C2	0.8921 (2)	0.6648 (3)	0.18439 (11)	0.0171 (4)
H2A	0.938919	0.750832	0.207388	0.020*
H2B	0.883119	0.701163	0.130732	0.020*
C3	1.0104 (3)	0.5134 (3)	0.19820 (12)	0.0213 (4)
H3A	1.125188	0.539814	0.184149	0.026*
H3B	0.976698	0.434485	0.167193	0.026*
C4	1.0091 (3)	0.4392 (3)	0.27921 (12)	0.0213 (4)
H4A	0.917598	0.367027	0.286961	0.026*
H4B	1.115861	0.373158	0.291258	0.026*
C5	0.9859 (2)	0.5642 (3)	0.33123 (11)	0.0174 (4)
H5A	1.023010	0.513272	0.381095	0.021*
H5B	1.059496	0.650951	0.315169	0.021*
C6	0.5966 (2)	0.6117 (2)	0.16227 (10)	0.0124 (3)
C7	0.5467 (2)	0.7364 (2)	0.10569 (11)	0.0153 (4)
C8	0.4260 (2)	0.7074 (3)	0.05574 (11)	0.0166 (4)
H8	0.390580	0.790458	0.017058	0.020*
C9	0.3562 (2)	0.5609 (3)	0.06083 (11)	0.0161 (4)
C10	0.4131 (2)	0.4383 (3)	0.11640 (11)	0.0152 (4)
H10	0.368015	0.336960	0.119653	0.018*
C11	0.5342 (2)	0.4601 (2)	0.16731 (11)	0.0142 (4)
C12	0.6139 (3)	0.8991 (3)	0.09724 (12)	0.0195 (4)
H12A	0.659427	0.917317	0.144502	0.029*
H12B	0.523485	0.982209	0.081462	0.029*
H12C	0.702474	0.903782	0.060256	0.029*
C13	0.2204 (3)	0.5367 (3)	0.00849 (12)	0.0211 (4)
H13A	0.260793	0.557117	−0.042190	0.032*
H13B	0.122623	0.611284	0.014537	0.032*
H13C	0.189295	0.425822	0.018970	0.032*
C14	0.5958 (3)	0.3205 (3)	0.22395 (12)	0.0195 (4)
H14A	0.523549	0.232564	0.223496	0.029*
H14B	0.593290	0.354708	0.272823	0.029*
H14C	0.710585	0.283492	0.212389	0.029*
C15	0.7790 (2)	0.7038 (2)	0.40398 (10)	0.0143 (4)
C16	0.7841 (3)	0.8691 (3)	0.40316 (12)	0.0177 (4)
C17	0.7552 (3)	0.9309 (3)	0.46878 (12)	0.0219 (4)
H17	0.758966	1.043068	0.469232	0.026*
C18	0.7208 (3)	0.8329 (3)	0.53399 (12)	0.0214 (4)
C19	0.7181 (3)	0.6689 (3)	0.53267 (11)	0.0191 (4)
H19	0.694640	0.601188	0.576813	0.023*
C20	0.7489 (2)	0.6004 (3)	0.46836 (11)	0.0162 (4)
C21	0.8131 (3)	0.9791 (3)	0.33286 (13)	0.0246 (5)
H21A	0.915278	0.939446	0.309426	0.037*
H21B	0.825083	1.087843	0.344006	0.037*
H21C	0.717856	0.981446	0.299430	0.037*
C22	0.6869 (4)	0.9050 (3)	0.60399 (13)	0.0334 (6)
H22A	0.626906	0.830949	0.638611	0.050*
H22B	0.618810	1.007566	0.592576	0.050*
H22C	0.793168	0.923296	0.626177	0.050*
C23	0.7446 (3)	0.4213 (3)	0.46971 (12)	0.0215 (4)
H23A	0.699897	0.399999	0.422795	0.032*
H23B	0.673019	0.378779	0.509995	0.032*
H23C	0.858093	0.368904	0.477201	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01234 (6)	0.01620 (6)	0.01713 (6)	−0.00217 (4)	0.00048 (4)	−0.00470 (5)
I2	0.02417 (8)	0.01847 (7)	0.03804 (9)	−0.00253 (5)	−0.01007 (6)	0.00498 (6)
Se1	0.01164 (9)	0.02445 (11)	0.01261 (9)	0.00002 (7)	0.00115 (7)	−0.00026 (8)
N1	0.0114 (7)	0.0165 (8)	0.0117 (7)	−0.0045 (6)	0.0011 (6)	−0.0020 (6)
N2	0.0130 (7)	0.0155 (8)	0.0116 (7)	−0.0012 (6)	−0.0012 (6)	−0.0008 (6)
C1	0.0122 (8)	0.0121 (9)	0.0130 (9)	−0.0012 (7)	−0.0004 (7)	0.0000 (7)
C2	0.0134 (9)	0.0242 (11)	0.0145 (9)	−0.0060 (8)	0.0032 (7)	−0.0032 (8)
C3	0.0166 (9)	0.0268 (12)	0.0225 (11)	−0.0011 (8)	0.0042 (8)	−0.0107 (9)
C4	0.0170 (9)	0.0206 (11)	0.0260 (11)	0.0038 (8)	−0.0004 (8)	−0.0049 (9)
C5	0.0133 (9)	0.0213 (10)	0.0169 (9)	0.0009 (7)	−0.0011 (7)	−0.0017 (8)
C6	0.0112 (8)	0.0161 (9)	0.0103 (8)	−0.0019 (7)	−0.0004 (6)	−0.0022 (7)
C7	0.0150 (9)	0.0173 (10)	0.0134 (9)	−0.0024 (7)	0.0020 (7)	−0.0013 (7)
C8	0.0149 (9)	0.0217 (10)	0.0121 (9)	0.0000 (7)	−0.0012 (7)	0.0002 (7)
C9	0.0118 (8)	0.0235 (10)	0.0137 (9)	−0.0010 (7)	−0.0002 (7)	−0.0049 (8)
C10	0.0123 (8)	0.0176 (10)	0.0160 (9)	−0.0029 (7)	0.0002 (7)	−0.0026 (7)
C11	0.0125 (8)	0.0175 (10)	0.0126 (9)	−0.0014 (7)	0.0005 (7)	−0.0015 (7)
C12	0.0222 (10)	0.0168 (10)	0.0186 (10)	−0.0044 (8)	0.0001 (8)	0.0021 (8)
C13	0.0150 (9)	0.0325 (12)	0.0167 (10)	−0.0051 (8)	−0.0030 (7)	−0.0047 (9)
C14	0.0192 (10)	0.0179 (10)	0.0206 (10)	−0.0033 (8)	−0.0040 (8)	0.0018 (8)
C15	0.0134 (8)	0.0181 (10)	0.0113 (8)	−0.0001 (7)	−0.0016 (7)	−0.0020 (7)
C16	0.0180 (9)	0.0168 (10)	0.0177 (10)	−0.0005 (7)	−0.0029 (7)	−0.0005 (8)
C17	0.0285 (11)	0.0161 (10)	0.0218 (11)	0.0003 (8)	−0.0027 (9)	−0.0058 (8)
C18	0.0211 (10)	0.0270 (12)	0.0160 (10)	0.0050 (8)	−0.0039 (8)	−0.0065 (8)
C19	0.0192 (9)	0.0256 (11)	0.0109 (9)	0.0007 (8)	−0.0022 (7)	0.0008 (8)
C20	0.0147 (9)	0.0196 (10)	0.0139 (9)	−0.0014 (7)	−0.0024 (7)	−0.0013 (7)
C21	0.0358 (13)	0.0156 (10)	0.0216 (11)	−0.0037 (9)	0.0030 (9)	0.0010 (8)
C22	0.0445 (15)	0.0367 (15)	0.0196 (11)	0.0087 (12)	−0.0030 (10)	−0.0130 (10)
C23	0.0263 (11)	0.0192 (11)	0.0183 (10)	−0.0052 (8)	−0.0025 (8)	0.0017 (8)

Geometric parameters (Å, º)

I1—I2	2.9107 (3)	C11—C14	1.506 (3)
I1—Se1	2.7558 (3)	C12—H12A	0.9800
Se1—C1	1.8974 (19)	C12—H12B	0.9800
N1—C1	1.334 (2)	C12—H12C	0.9800
N1—C2	1.487 (2)	C13—H13A	0.9800
N1—C6	1.450 (2)	C13—H13B	0.9800
N2—C1	1.351 (2)	C13—H13C	0.9800
N2—C5	1.491 (3)	C14—H14A	0.9800
N2—C15	1.450 (2)	C14—H14B	0.9800
C2—H2A	0.9900	C14—H14C	0.9800
C2—H2B	0.9900	C15—C16	1.396 (3)
C2—C3	1.517 (3)	C15—C20	1.398 (3)
C3—H3A	0.9900	C16—C17	1.390 (3)
C3—H3B	0.9900	C16—C21	1.507 (3)
C3—C4	1.529 (3)	C17—H17	0.9500
C4—H4A	0.9900	C17—C18	1.394 (3)
C4—H4B	0.9900	C18—C19	1.388 (3)
C4—C5	1.519 (3)	C18—C22	1.512 (3)
C5—H5A	0.9900	C19—H19	0.9500
C5—H5B	0.9900	C19—C20	1.398 (3)
C6—C7	1.402 (3)	C20—C23	1.509 (3)
C6—C11	1.403 (3)	C21—H21A	0.9800
C7—C8	1.397 (3)	C21—H21B	0.9800
C7—C12	1.503 (3)	C21—H21C	0.9800
C8—H8	0.9500	C22—H22A	0.9800
C8—C9	1.390 (3)	C22—H22B	0.9800
C9—C10	1.393 (3)	C22—H22C	0.9800
C9—C13	1.502 (3)	C23—H23A	0.9800
C10—H10	0.9500	C23—H23B	0.9800
C10—C11	1.392 (3)	C23—H23C	0.9800
Se1—I1—I2	174.620 (7)	C7—C12—H12B	109.5
C1—Se1—I1	109.28 (6)	C7—C12—H12C	109.5
C1—N1—C2	120.77 (16)	H12A—C12—H12B	109.5
C1—N1—C6	122.74 (16)	H12A—C12—H12C	109.5
C6—N1—C2	116.43 (15)	H12B—C12—H12C	109.5
C1—N2—C5	127.28 (17)	C9—C13—H13A	109.5
C1—N2—C15	119.63 (16)	C9—C13—H13B	109.5
C15—N2—C5	113.08 (15)	C9—C13—H13C	109.5
N1—C1—Se1	122.92 (14)	H13A—C13—H13B	109.5
N1—C1—N2	121.70 (17)	H13A—C13—H13C	109.5
N2—C1—Se1	115.36 (14)	H13B—C13—H13C	109.5
N1—C2—H2A	109.1	C11—C14—H14A	109.5
N1—C2—H2B	109.1	C11—C14—H14B	109.5
N1—C2—C3	112.44 (17)	C11—C14—H14C	109.5
H2A—C2—H2B	107.8	H14A—C14—H14B	109.5
C3—C2—H2A	109.1	H14A—C14—H14C	109.5
C3—C2—H2B	109.1	H14B—C14—H14C	109.5
C2—C3—H3A	109.4	C16—C15—N2	118.39 (18)
C2—C3—H3B	109.4	C16—C15—C20	122.13 (18)
C2—C3—C4	110.98 (17)	C20—C15—N2	119.45 (18)
H3A—C3—H3B	108.0	C15—C16—C21	121.32 (19)
C4—C3—H3A	109.4	C17—C16—C15	118.01 (19)
C4—C3—H3B	109.4	C17—C16—C21	120.6 (2)
C3—C4—H4A	109.0	C16—C17—H17	119.1
C3—C4—H4B	109.0	C16—C17—C18	121.9 (2)
H4A—C4—H4B	107.8	C18—C17—H17	119.1
C5—C4—C3	112.99 (18)	C17—C18—C22	120.3 (2)
C5—C4—H4A	109.0	C19—C18—C17	118.4 (2)
C5—C4—H4B	109.0	C19—C18—C22	121.3 (2)
N2—C5—C4	114.95 (17)	C18—C19—H19	119.0
N2—C5—H5A	108.5	C18—C19—C20	122.0 (2)
N2—C5—H5B	108.5	C20—C19—H19	119.0
C4—C5—H5A	108.5	C15—C20—C19	117.57 (19)
C4—C5—H5B	108.5	C15—C20—C23	122.36 (18)
H5A—C5—H5B	107.5	C19—C20—C23	120.05 (19)
C7—C6—N1	118.43 (17)	C16—C21—H21A	109.5
C7—C6—C11	121.73 (17)	C16—C21—H21B	109.5
C11—C6—N1	119.76 (17)	C16—C21—H21C	109.5
C6—C7—C12	123.38 (18)	H21A—C21—H21B	109.5
C8—C7—C6	117.75 (18)	H21A—C21—H21C	109.5
C8—C7—C12	118.87 (19)	H21B—C21—H21C	109.5
C7—C8—H8	118.9	C18—C22—H22A	109.5
C9—C8—C7	122.10 (19)	C18—C22—H22B	109.5
C9—C8—H8	118.9	C18—C22—H22C	109.5
C8—C9—C10	118.37 (18)	H22A—C22—H22B	109.5
C8—C9—C13	120.66 (19)	H22A—C22—H22C	109.5
C10—C9—C13	120.95 (19)	H22B—C22—H22C	109.5
C9—C10—H10	119.0	C20—C23—H23A	109.5
C11—C10—C9	121.95 (19)	C20—C23—H23B	109.5
C11—C10—H10	119.0	C20—C23—H23C	109.5
C6—C11—C14	122.70 (17)	H23A—C23—H23B	109.5
C10—C11—C6	118.00 (18)	H23A—C23—H23C	109.5
C10—C11—C14	119.28 (18)	H23B—C23—H23C	109.5
C7—C12—H12A	109.5
I1—Se1—C1—N1	−41.46 (18)	C6—N1—C2—C3	−98.8 (2)
I1—Se1—C1—N2	140.31 (13)	C6—C7—C8—C9	−0.1 (3)
N1—C2—C3—C4	−50.7 (2)	C7—C6—C11—C10	−3.4 (3)
N1—C6—C7—C8	179.68 (17)	C7—C6—C11—C14	175.07 (19)
N1—C6—C7—C12	−1.6 (3)	C7—C8—C9—C10	−2.0 (3)
N1—C6—C11—C10	179.81 (17)	C7—C8—C9—C13	176.87 (19)
N1—C6—C11—C14	−1.7 (3)	C8—C9—C10—C11	1.4 (3)
N2—C15—C16—C17	−179.11 (18)	C9—C10—C11—C6	1.2 (3)
N2—C15—C16—C21	3.3 (3)	C9—C10—C11—C14	−177.31 (19)
N2—C15—C20—C19	−179.96 (17)	C11—C6—C7—C8	2.8 (3)
N2—C15—C20—C23	−1.6 (3)	C11—C6—C7—C12	−178.41 (19)
C1—N1—C2—C3	84.0 (2)	C12—C7—C8—C9	−178.89 (19)
C1—N1—C6—C7	111.8 (2)	C13—C9—C10—C11	−177.44 (19)
C1—N1—C6—C11	−71.3 (3)	C15—N2—C1—Se1	−23.4 (2)
C1—N2—C5—C4	−24.0 (3)	C15—N2—C1—N1	158.31 (18)
C1—N2—C15—C16	−79.9 (2)	C15—N2—C5—C4	156.80 (18)
C1—N2—C15—C20	102.1 (2)	C15—C16—C17—C18	−0.4 (3)
C2—N1—C1—Se1	163.19 (15)	C16—C15—C20—C19	2.1 (3)
C2—N1—C1—N2	−18.7 (3)	C16—C15—C20—C23	−179.51 (19)
C2—N1—C6—C7	−65.4 (2)	C16—C17—C18—C19	0.9 (3)
C2—N1—C6—C11	111.5 (2)	C16—C17—C18—C22	−178.9 (2)
C2—C3—C4—C5	−34.7 (2)	C17—C18—C19—C20	0.1 (3)
C3—C4—C5—N2	76.8 (2)	C18—C19—C20—C15	−1.5 (3)
C5—N2—C1—Se1	157.43 (16)	C18—C19—C20—C23	−180.0 (2)
C5—N2—C1—N1	−20.8 (3)	C20—C15—C16—C17	−1.1 (3)
C5—N2—C15—C16	99.3 (2)	C20—C15—C16—C21	−178.7 (2)
C5—N2—C15—C20	−78.7 (2)	C21—C16—C17—C18	177.2 (2)
C6—N1—C1—Se1	−13.8 (3)	C22—C18—C19—C20	179.9 (2)
C6—N1—C1—N2	164.29 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···I1^i	0.99	3.08	3.885 (2)	139
C3—H3B···I2^ii	0.99	3.14	4.007 (2)	147
C5—H5B···I1^i	0.99	3.11	4.067 (2)	164

Symmetry codes: (i) x+1, y, z; (ii) x+1, y−1, z.

(SDiazMesSI2_I2)

Crystal data

2(C23H30I2N2S)·2(I2)	Z = 1
Mr = 1748.30	F(000) = 820
Triclinic, P1	Dx = 2.062 Mg m^−3
a = 8.3022 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.3510 (11) Å	Cell parameters from 71058 reflections
c = 15.5656 (16) Å	θ = 2.2–30.1°
α = 83.691 (4)°	µ = 4.51 mm^−1
β = 87.180 (4)°	T = 100 K
γ = 75.024 (4)°	Plank, red
V = 1408.1 (3) Å^3	0.19 × 0.09 × 0.04 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	7603 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.035
φ and ω scans	θmax = 30.1°, θmin = 2.2°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −11→11
Tmin = 0.579, Tmax = 0.746	k = −15→15
71058 measured reflections	l = −21→21
8260 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.017	H-atom parameters constrained
wR(F^2) = 0.039	w = 1/[σ^2(Fo^2) + (0.0082P)^2 + 1.3172P] where P = (Fo^2 + 2Fc^2)/3
S = 1.18	(Δ/σ)max = 0.005
8260 reflections	Δρmax = 0.50 e Å^−3
277 parameters	Δρmin = −0.74 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.31247 (2)	0.58104 (2)	0.72662 (2)	0.01485 (3)
I2	0.10499 (2)	0.81980 (2)	0.79506 (2)	0.02312 (3)
S1	0.48485 (5)	0.37844 (4)	0.68562 (3)	0.01452 (8)
N1	0.77284 (18)	0.42648 (13)	0.72581 (9)	0.0121 (3)
N2	0.70824 (18)	0.25045 (13)	0.79742 (10)	0.0124 (3)
C1	0.6709 (2)	0.35257 (15)	0.74190 (11)	0.0120 (3)
C2	0.9150 (2)	0.41687 (16)	0.78278 (12)	0.0145 (3)
H2A	0.879573	0.401677	0.843769	0.017*
H2B	0.947045	0.495588	0.776116	0.017*
C3	1.0651 (2)	0.31443 (17)	0.76182 (13)	0.0172 (3)
H3A	1.150861	0.303678	0.806012	0.021*
H3B	1.113839	0.337002	0.705007	0.021*
C4	1.0164 (2)	0.19328 (16)	0.75944 (12)	0.0158 (3)
H4A	0.978858	0.189301	0.700675	0.019*
H4B	1.115986	0.124249	0.771265	0.019*
C5	0.8792 (2)	0.17845 (16)	0.82443 (12)	0.0158 (3)
H5A	0.880415	0.090566	0.834195	0.019*
H5B	0.903450	0.204181	0.880113	0.019*
C6	0.7473 (2)	0.52375 (16)	0.65478 (11)	0.0132 (3)
C7	0.7003 (2)	0.64546 (16)	0.67572 (12)	0.0150 (3)
C8	0.6790 (2)	0.73859 (17)	0.60760 (13)	0.0178 (3)
H8	0.646832	0.821473	0.620441	0.021*
C9	0.7031 (2)	0.71437 (17)	0.52180 (12)	0.0184 (4)
C10	0.7531 (2)	0.59230 (17)	0.50401 (12)	0.0173 (3)
H10	0.772011	0.574714	0.445544	0.021*
C11	0.7763 (2)	0.49498 (16)	0.56929 (12)	0.0147 (3)
C12	0.6723 (2)	0.68036 (17)	0.76724 (12)	0.0183 (4)
H12A	0.652467	0.610928	0.805702	0.027*
H12B	0.575198	0.750766	0.769518	0.027*
H12C	0.771115	0.702017	0.785849	0.027*
C13	0.6764 (3)	0.81838 (19)	0.45019 (14)	0.0286 (5)
H13A	0.774137	0.852266	0.444659	0.043*
H13B	0.577350	0.882600	0.463880	0.043*
H13C	0.660499	0.787714	0.395607	0.043*
C14	0.8295 (3)	0.36548 (17)	0.54486 (13)	0.0201 (4)
H14A	0.733583	0.329626	0.550029	0.030*
H14B	0.917088	0.316675	0.583581	0.030*
H14C	0.872482	0.365931	0.485078	0.030*
C15	0.5758 (2)	0.20126 (16)	0.83975 (11)	0.0124 (3)
C16	0.5412 (2)	0.09825 (16)	0.81058 (11)	0.0132 (3)
C17	0.4238 (2)	0.04684 (16)	0.85725 (12)	0.0156 (3)
H17	0.398277	−0.022819	0.838184	0.019*
C18	0.3431 (2)	0.09504 (17)	0.93107 (12)	0.0155 (3)
C19	0.3811 (2)	0.19780 (17)	0.95803 (12)	0.0164 (3)
H19	0.326392	0.231434	1.008190	0.020*
C20	0.4973 (2)	0.25261 (16)	0.91329 (12)	0.0149 (3)
C21	0.6261 (2)	0.04315 (17)	0.73114 (12)	0.0179 (3)
H21A	0.651908	0.107845	0.689961	0.027*
H21B	0.551959	0.003877	0.704275	0.027*
H21C	0.729574	−0.018074	0.747544	0.027*
C22	0.2200 (2)	0.03633 (19)	0.98208 (13)	0.0204 (4)
H22A	0.277600	−0.021930	1.028818	0.031*
H22B	0.170277	−0.007021	0.943838	0.031*
H22C	0.132084	0.099815	1.006728	0.031*
C23	0.5348 (3)	0.36361 (18)	0.94498 (13)	0.0209 (4)
H23A	0.653924	0.345900	0.956892	0.031*
H23B	0.469576	0.383619	0.998038	0.031*
H23C	0.505129	0.433311	0.900567	0.031*
I3	0.02911 (2)	0.94288 (2)	0.58243 (2)	0.02671 (3)
I4	0.03703 (2)	0.59671 (2)	0.94795 (2)	0.02033 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01177 (5)	0.01314 (5)	0.01889 (6)	−0.00229 (4)	−0.00107 (4)	−0.00022 (4)
I2	0.02082 (6)	0.01405 (6)	0.03315 (7)	−0.00142 (5)	0.00298 (5)	−0.00554 (5)
S1	0.01187 (18)	0.01179 (18)	0.0202 (2)	−0.00258 (15)	−0.00434 (15)	−0.00206 (15)
N1	0.0128 (7)	0.0105 (6)	0.0135 (7)	−0.0038 (5)	−0.0023 (5)	−0.0006 (5)
N2	0.0093 (6)	0.0114 (6)	0.0161 (7)	−0.0025 (5)	−0.0001 (5)	0.0007 (5)
C1	0.0116 (7)	0.0117 (7)	0.0128 (7)	−0.0024 (6)	−0.0003 (6)	−0.0035 (6)
C2	0.0141 (8)	0.0137 (8)	0.0169 (8)	−0.0050 (6)	−0.0056 (6)	−0.0008 (6)
C3	0.0126 (8)	0.0168 (8)	0.0224 (9)	−0.0046 (6)	−0.0023 (7)	0.0006 (7)
C4	0.0105 (7)	0.0144 (8)	0.0217 (9)	−0.0020 (6)	−0.0011 (6)	−0.0005 (7)
C5	0.0120 (8)	0.0137 (8)	0.0201 (9)	−0.0015 (6)	−0.0022 (6)	0.0021 (6)
C6	0.0131 (8)	0.0109 (7)	0.0162 (8)	−0.0047 (6)	−0.0020 (6)	0.0004 (6)
C7	0.0154 (8)	0.0126 (8)	0.0185 (8)	−0.0054 (6)	−0.0016 (6)	−0.0032 (6)
C8	0.0205 (9)	0.0114 (8)	0.0221 (9)	−0.0051 (7)	−0.0025 (7)	−0.0012 (7)
C9	0.0211 (9)	0.0159 (8)	0.0191 (9)	−0.0073 (7)	−0.0034 (7)	0.0028 (7)
C10	0.0207 (9)	0.0180 (9)	0.0144 (8)	−0.0070 (7)	−0.0029 (7)	−0.0004 (7)
C11	0.0147 (8)	0.0139 (8)	0.0160 (8)	−0.0042 (6)	−0.0011 (6)	−0.0014 (6)
C12	0.0225 (9)	0.0145 (8)	0.0194 (9)	−0.0059 (7)	0.0004 (7)	−0.0054 (7)
C13	0.0453 (13)	0.0180 (9)	0.0234 (10)	−0.0113 (9)	−0.0081 (9)	0.0051 (8)
C14	0.0259 (10)	0.0163 (9)	0.0179 (9)	−0.0040 (7)	0.0011 (7)	−0.0045 (7)
C15	0.0104 (7)	0.0124 (7)	0.0138 (8)	−0.0026 (6)	0.0000 (6)	0.0004 (6)
C16	0.0130 (8)	0.0114 (7)	0.0141 (8)	−0.0014 (6)	−0.0016 (6)	0.0001 (6)
C17	0.0132 (8)	0.0116 (8)	0.0221 (9)	−0.0039 (6)	−0.0033 (7)	0.0003 (6)
C18	0.0109 (8)	0.0169 (8)	0.0175 (8)	−0.0032 (6)	−0.0012 (6)	0.0035 (6)
C19	0.0134 (8)	0.0182 (8)	0.0167 (8)	−0.0023 (7)	0.0004 (6)	−0.0021 (7)
C20	0.0126 (8)	0.0145 (8)	0.0173 (8)	−0.0024 (6)	−0.0019 (6)	−0.0016 (6)
C21	0.0194 (9)	0.0144 (8)	0.0198 (9)	−0.0033 (7)	0.0016 (7)	−0.0053 (7)
C22	0.0155 (8)	0.0228 (9)	0.0224 (9)	−0.0074 (7)	0.0016 (7)	0.0048 (7)
C23	0.0222 (9)	0.0209 (9)	0.0221 (9)	−0.0078 (7)	0.0013 (7)	−0.0084 (7)
I3	0.03372 (8)	0.02322 (7)	0.02649 (7)	−0.01250 (6)	0.00947 (5)	−0.00872 (5)
I4	0.01638 (6)	0.02723 (7)	0.01854 (6)	−0.00494 (5)	−0.00107 (4)	−0.00853 (5)

Geometric parameters (Å, º)

I1—I2	3.0803 (3)	C12—H12A	0.9800
I1—S1	2.5053 (5)	C12—H12B	0.9800
S1—C1	1.7559 (18)	C12—H12C	0.9800
N1—C1	1.335 (2)	C13—H13A	0.9800
N1—C2	1.485 (2)	C13—H13B	0.9800
N1—C6	1.456 (2)	C13—H13C	0.9800
N2—C1	1.344 (2)	C14—H14A	0.9800
N2—C5	1.498 (2)	C14—H14B	0.9800
N2—C15	1.456 (2)	C14—H14C	0.9800
C2—H2A	0.9900	C15—C16	1.400 (2)
C2—H2B	0.9900	C15—C20	1.397 (2)
C2—C3	1.519 (3)	C16—C17	1.396 (2)
C3—H3A	0.9900	C16—C21	1.508 (2)
C3—H3B	0.9900	C17—H17	0.9500
C3—C4	1.535 (3)	C17—C18	1.393 (3)
C4—H4A	0.9900	C18—C19	1.395 (3)
C4—H4B	0.9900	C18—C22	1.509 (2)
C4—C5	1.516 (3)	C19—H19	0.9500
C5—H5A	0.9900	C19—C20	1.397 (2)
C5—H5B	0.9900	C20—C23	1.510 (3)
C6—C7	1.405 (2)	C21—H21A	0.9800
C6—C11	1.400 (2)	C21—H21B	0.9800
C7—C8	1.396 (3)	C21—H21C	0.9800
C7—C12	1.511 (3)	C22—H22A	0.9800
C8—H8	0.9500	C22—H22B	0.9800
C8—C9	1.388 (3)	C22—H22C	0.9800
C9—C10	1.394 (3)	C23—H23A	0.9800
C9—C13	1.512 (3)	C23—H23B	0.9800
C10—H10	0.9500	C23—H23C	0.9800
C10—C11	1.397 (2)	I3—I3^i	2.7507 (4)
C11—C14	1.507 (3)	I4—I4^ii	2.7645 (3)
S1—I1—I2	174.564 (12)	C7—C12—H12B	109.5
C1—S1—I1	104.65 (6)	C7—C12—H12C	109.5
C1—N1—C2	121.09 (14)	H12A—C12—H12B	109.5
C1—N1—C6	122.46 (15)	H12A—C12—H12C	109.5
C6—N1—C2	116.39 (13)	H12B—C12—H12C	109.5
C1—N2—C5	126.41 (14)	C9—C13—H13A	109.5
C1—N2—C15	120.30 (14)	C9—C13—H13B	109.5
C15—N2—C5	113.27 (13)	C9—C13—H13C	109.5
N1—C1—S1	121.32 (13)	H13A—C13—H13B	109.5
N1—C1—N2	122.70 (16)	H13A—C13—H13C	109.5
N2—C1—S1	115.85 (12)	H13B—C13—H13C	109.5
N1—C2—H2A	109.2	C11—C14—H14A	109.5
N1—C2—H2B	109.2	C11—C14—H14B	109.5
N1—C2—C3	111.99 (15)	C11—C14—H14C	109.5
H2A—C2—H2B	107.9	H14A—C14—H14B	109.5
C3—C2—H2A	109.2	H14A—C14—H14C	109.5
C3—C2—H2B	109.2	H14B—C14—H14C	109.5
C2—C3—H3A	109.4	C16—C15—N2	119.45 (15)
C2—C3—H3B	109.4	C20—C15—N2	118.26 (15)
C2—C3—C4	111.23 (15)	C20—C15—C16	122.05 (16)
H3A—C3—H3B	108.0	C15—C16—C21	121.90 (16)
C4—C3—H3A	109.4	C17—C16—C15	118.02 (16)
C4—C3—H3B	109.4	C17—C16—C21	120.08 (16)
C3—C4—H4A	109.0	C16—C17—H17	119.1
C3—C4—H4B	109.0	C18—C17—C16	121.70 (17)
H4A—C4—H4B	107.8	C18—C17—H17	119.1
C5—C4—C3	112.93 (16)	C17—C18—C19	118.53 (16)
C5—C4—H4A	109.0	C17—C18—C22	121.01 (17)
C5—C4—H4B	109.0	C19—C18—C22	120.45 (17)
N2—C5—C4	114.08 (14)	C18—C19—H19	119.1
N2—C5—H5A	108.7	C18—C19—C20	121.81 (17)
N2—C5—H5B	108.7	C20—C19—H19	119.1
C4—C5—H5A	108.7	C15—C20—C19	117.88 (16)
C4—C5—H5B	108.7	C15—C20—C23	122.14 (16)
H5A—C5—H5B	107.6	C19—C20—C23	119.98 (17)
C7—C6—N1	117.67 (15)	C16—C21—H21A	109.5
C11—C6—N1	120.20 (15)	C16—C21—H21B	109.5
C11—C6—C7	122.07 (16)	C16—C21—H21C	109.5
C6—C7—C12	123.71 (16)	H21A—C21—H21B	109.5
C8—C7—C6	117.60 (17)	H21A—C21—H21C	109.5
C8—C7—C12	118.70 (16)	H21B—C21—H21C	109.5
C7—C8—H8	118.8	C18—C22—H22A	109.5
C9—C8—C7	122.31 (17)	C18—C22—H22B	109.5
C9—C8—H8	118.8	C18—C22—H22C	109.5
C8—C9—C10	118.20 (17)	H22A—C22—H22B	109.5
C8—C9—C13	120.37 (18)	H22A—C22—H22C	109.5
C10—C9—C13	121.43 (18)	H22B—C22—H22C	109.5
C9—C10—H10	118.9	C20—C23—H23A	109.5
C9—C10—C11	122.22 (17)	C20—C23—H23B	109.5
C11—C10—H10	118.9	C20—C23—H23C	109.5
C6—C11—C14	123.33 (16)	H23A—C23—H23B	109.5
C10—C11—C6	117.58 (16)	H23A—C23—H23C	109.5
C10—C11—C14	119.09 (16)	H23B—C23—H23C	109.5
C7—C12—H12A	109.5
I1—S1—C1—N1	−63.56 (15)	C6—N1—C2—C3	−101.40 (17)
I1—S1—C1—N2	120.48 (12)	C6—C7—C8—C9	−0.3 (3)
N1—C2—C3—C4	−51.4 (2)	C7—C6—C11—C10	−1.5 (3)
N1—C6—C7—C8	178.79 (16)	C7—C6—C11—C14	178.94 (17)
N1—C6—C7—C12	−1.1 (3)	C7—C8—C9—C10	−1.1 (3)
N1—C6—C11—C10	−178.63 (16)	C7—C8—C9—C13	179.24 (19)
N1—C6—C11—C14	1.8 (3)	C8—C9—C10—C11	1.2 (3)
N2—C15—C16—C17	174.43 (15)	C9—C10—C11—C6	0.1 (3)
N2—C15—C16—C21	−5.8 (3)	C9—C10—C11—C14	179.67 (18)
N2—C15—C20—C19	−174.33 (16)	C11—C6—C7—C8	1.6 (3)
N2—C15—C20—C23	5.5 (3)	C11—C6—C7—C12	−178.32 (17)
C1—N1—C2—C3	81.3 (2)	C12—C7—C8—C9	179.64 (18)
C1—N1—C6—C7	111.24 (19)	C13—C9—C10—C11	−179.15 (19)
C1—N1—C6—C11	−71.5 (2)	C15—N2—C1—S1	−29.4 (2)
C1—N2—C5—C4	−24.7 (2)	C15—N2—C1—N1	154.74 (16)
C1—N2—C15—C16	103.38 (19)	C15—N2—C5—C4	156.97 (15)
C1—N2—C15—C20	−82.1 (2)	C15—C16—C17—C18	−0.4 (3)
C2—N1—C1—S1	169.88 (13)	C16—C15—C20—C19	0.0 (3)
C2—N1—C1—N2	−14.4 (3)	C16—C15—C20—C23	179.88 (17)
C2—N1—C6—C7	−66.0 (2)	C16—C17—C18—C19	0.4 (3)
C2—N1—C6—C11	111.30 (18)	C16—C17—C18—C22	−178.36 (17)
C2—C3—C4—C5	−34.2 (2)	C17—C18—C19—C20	−0.2 (3)
C3—C4—C5—N2	77.8 (2)	C18—C19—C20—C15	0.0 (3)
C5—N2—C1—S1	152.39 (14)	C18—C19—C20—C23	−179.86 (17)
C5—N2—C1—N1	−23.5 (3)	C20—C15—C16—C17	0.1 (3)
C5—N2—C15—C16	−78.2 (2)	C20—C15—C16—C21	179.95 (17)
C5—N2—C15—C20	96.35 (19)	C21—C16—C17—C18	179.84 (17)
C6—N1—C1—S1	−7.2 (2)	C22—C18—C19—C20	178.55 (17)
C6—N1—C1—N2	168.47 (16)

Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···I4^iii	0.99	3.22	3.7794 (18)	118
C5—H5A···I2^iv	0.99	3.26	4.0837 (19)	142

Symmetry codes: (iii) x+1, y, z; (iv) x+1, y−1, z.

(SDiazMesSeI_I3)

Crystal data

C23H30IN2Se·I3	F(000) = 1712
Mr = 921.05	Dx = 2.183 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.0063 (7) Å	Cell parameters from 9954 reflections
b = 22.9632 (14) Å	θ = 2.5–27.5°
c = 11.1015 (6) Å	µ = 5.76 mm^−1
β = 93.024 (2)°	T = 100 K
V = 2801.9 (3) Å^3	Plate, red
Z = 4	0.06 × 0.06 × 0.02 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	5536 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.091
φ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −12→14
Tmin = 0.606, Tmax = 0.746	k = −29→29
36709 measured reflections	l = −13→14
6428 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H-atom parameters constrained
S = 1.17	w = 1/[σ^2(Fo^2) + (0.0131P)^2 + 65.9822P] where P = (Fo^2 + 2Fc^2)/3
6428 reflections	(Δ/σ)max = 0.001
278 parameters	Δρmax = 2.17 e Å^−3
30 restraints	Δρmin = −1.40 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.59561 (6)	0.64902 (3)	0.81087 (6)	0.01566 (15)
Se1	0.40931 (11)	0.71085 (5)	0.86165 (11)	0.0219 (3)
N1	0.2695 (8)	0.6471 (4)	0.6789 (7)	0.0128 (17)
N2	0.2234 (8)	0.7464 (4)	0.7042 (8)	0.0134 (17)
C1	0.2883 (9)	0.6986 (4)	0.7330 (9)	0.0106 (19)
C2	0.2029 (10)	0.6450 (5)	0.5580 (9)	0.020 (2)
H2A	0.226802	0.609281	0.515278	0.024*
H2B	0.227365	0.678895	0.509738	0.024*
C3	0.0654 (10)	0.6455 (5)	0.5662 (10)	0.019 (2)
H3A	0.026628	0.647727	0.483796	0.023*
H3B	0.039505	0.608654	0.603149	0.023*
C4	0.0220 (10)	0.6962 (4)	0.6399 (9)	0.014 (2)
H4A	0.020130	0.684114	0.725381	0.017*
H4B	−0.062112	0.706380	0.611500	0.017*
C5	0.1018 (10)	0.7498 (5)	0.6320 (10)	0.019 (2)
H5A	0.056192	0.783871	0.660497	0.022*
H5B	0.117801	0.756659	0.546226	0.022*
C6	0.3091 (10)	0.5925 (4)	0.7319 (9)	0.0133 (17)
C7	0.3935 (9)	0.5589 (4)	0.6712 (9)	0.0128 (16)
C8	0.4292 (10)	0.5065 (4)	0.7216 (9)	0.0141 (18)
H8	0.486185	0.483288	0.681713	0.017*
C9	0.3842 (10)	0.4860 (5)	0.8301 (10)	0.017 (2)
C10	0.2992 (10)	0.5200 (5)	0.8848 (9)	0.017 (2)
H10	0.266542	0.506303	0.957084	0.021*
C11	0.2594 (9)	0.5735 (4)	0.8382 (9)	0.013 (2)
C12	0.4501 (10)	0.5785 (5)	0.5575 (10)	0.018 (2)
H12A	0.536370	0.567731	0.561145	0.028*
H12B	0.442353	0.620851	0.549616	0.028*
H12C	0.408392	0.559617	0.487780	0.028*
C13	0.4292 (11)	0.4289 (5)	0.8833 (11)	0.025 (3)
H13A	0.496964	0.436212	0.942209	0.037*
H13B	0.456930	0.403765	0.818850	0.037*
H13C	0.362957	0.409560	0.923392	0.037*
C14	0.1644 (11)	0.6067 (5)	0.9025 (10)	0.021 (2)
H14A	0.125240	0.580667	0.958705	0.032*
H14B	0.103164	0.621865	0.843354	0.032*
H14C	0.202941	0.639129	0.947300	0.032*
C15	0.2641 (9)	0.8031 (4)	0.7498 (9)	0.013 (2)
C16	0.3472 (9)	0.8346 (4)	0.6817 (9)	0.013 (2)
C17	0.3851 (10)	0.8889 (5)	0.7275 (10)	0.0174 (18)
H17	0.440907	0.911377	0.684410	0.021*
C18	0.3424 (10)	0.9111 (5)	0.8364 (10)	0.0177 (14)
C19	0.2600 (10)	0.8784 (5)	0.8961 (10)	0.0168 (18)
H19	0.229178	0.893885	0.967695	0.020*
C20	0.2194 (10)	0.8242 (5)	0.8575 (10)	0.017 (2)
C21	0.3973 (11)	0.8098 (5)	0.5704 (10)	0.023 (2)
H21A	0.461063	0.781480	0.592938	0.034*
H21B	0.431815	0.841235	0.523107	0.034*
H21C	0.332025	0.790525	0.522082	0.034*
C22	0.3888 (10)	0.9692 (4)	0.8813 (10)	0.0178 (15)
H22A	0.477567	0.970319	0.878506	0.027*
H22B	0.365873	0.975012	0.964630	0.027*
H22C	0.353012	1.000216	0.830164	0.027*
C23	0.1302 (10)	0.7901 (5)	0.9276 (10)	0.021 (2)
H23A	0.049295	0.792481	0.886632	0.031*
H23B	0.127291	0.806367	1.009002	0.031*
H23C	0.155977	0.749298	0.932788	0.031*
I2	0.82187 (7)	0.56569 (3)	0.76383 (8)	0.02662 (19)
I3	0.76938 (6)	0.43650 (3)	0.76074 (6)	0.01781 (16)
I4	0.73525 (8)	0.31356 (3)	0.76667 (7)	0.02759 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0164 (3)	0.0133 (3)	0.0168 (3)	−0.0016 (3)	−0.0037 (2)	−0.0004 (3)
Se1	0.0208 (6)	0.0211 (6)	0.0225 (6)	0.0077 (5)	−0.0115 (5)	−0.0126 (4)
N1	0.018 (4)	0.008 (4)	0.012 (4)	0.001 (3)	−0.003 (3)	0.004 (3)
N2	0.014 (4)	0.007 (4)	0.018 (4)	0.001 (3)	−0.005 (3)	0.002 (3)
C1	0.006 (4)	0.013 (5)	0.013 (5)	−0.002 (4)	0.004 (4)	0.001 (4)
C2	0.025 (6)	0.022 (6)	0.013 (5)	−0.009 (5)	0.002 (4)	−0.006 (4)
C3	0.025 (6)	0.013 (5)	0.019 (5)	−0.004 (4)	−0.005 (5)	0.005 (4)
C4	0.019 (5)	0.009 (5)	0.014 (5)	−0.005 (4)	−0.006 (4)	0.000 (4)
C5	0.017 (5)	0.017 (5)	0.021 (5)	0.000 (4)	−0.003 (4)	0.002 (4)
C6	0.014 (4)	0.012 (4)	0.014 (4)	0.000 (3)	−0.004 (3)	−0.003 (3)
C7	0.013 (3)	0.011 (3)	0.015 (3)	0.000 (3)	−0.002 (3)	−0.006 (3)
C8	0.014 (4)	0.014 (4)	0.015 (4)	0.003 (3)	0.001 (3)	−0.006 (3)
C9	0.022 (6)	0.012 (5)	0.017 (5)	−0.007 (4)	−0.005 (4)	−0.005 (4)
C10	0.018 (5)	0.021 (6)	0.013 (5)	−0.007 (4)	−0.002 (4)	−0.003 (4)
C11	0.012 (5)	0.015 (5)	0.011 (5)	0.000 (4)	−0.005 (4)	−0.001 (4)
C12	0.017 (5)	0.019 (6)	0.019 (5)	0.007 (4)	0.007 (4)	0.003 (4)
C13	0.019 (6)	0.026 (6)	0.029 (6)	−0.003 (5)	−0.010 (5)	−0.003 (5)
C14	0.024 (6)	0.027 (6)	0.012 (5)	0.010 (5)	0.006 (4)	0.005 (4)
C15	0.012 (5)	0.006 (5)	0.021 (5)	0.002 (4)	−0.008 (4)	−0.002 (4)
C16	0.015 (5)	0.014 (5)	0.011 (5)	−0.001 (4)	0.003 (4)	−0.004 (4)
C17	0.012 (4)	0.014 (4)	0.026 (4)	−0.002 (3)	−0.005 (3)	0.000 (3)
C18	0.014 (3)	0.012 (3)	0.026 (3)	−0.001 (3)	−0.008 (3)	−0.003 (3)
C19	0.017 (4)	0.013 (4)	0.020 (4)	0.000 (3)	−0.006 (3)	−0.002 (3)
C20	0.012 (5)	0.012 (5)	0.027 (6)	−0.003 (4)	−0.004 (4)	0.004 (4)
C21	0.022 (6)	0.024 (6)	0.023 (6)	−0.003 (5)	0.009 (5)	0.001 (5)
C22	0.014 (3)	0.012 (3)	0.027 (3)	−0.002 (3)	−0.008 (3)	−0.003 (3)
C23	0.023 (6)	0.014 (5)	0.026 (6)	0.000 (4)	0.007 (5)	−0.003 (4)
I2	0.0221 (4)	0.0214 (4)	0.0370 (5)	0.0032 (3)	0.0071 (3)	−0.0011 (3)
I3	0.0159 (3)	0.0253 (4)	0.0121 (3)	0.0018 (3)	−0.0008 (2)	0.0001 (3)
I4	0.0392 (5)	0.0260 (4)	0.0174 (4)	−0.0077 (3)	−0.0001 (3)	0.0027 (3)

Geometric parameters (Å, º)

I1—Se1	2.5806 (13)	C12—H12B	0.9800
Se1—C1	1.921 (10)	C12—H12C	0.9800
N1—C1	1.339 (13)	C13—H13A	0.9800
N1—C2	1.496 (13)	C13—H13B	0.9800
N1—C6	1.441 (13)	C13—H13C	0.9800
N2—C1	1.339 (13)	C14—H14A	0.9800
N2—C5	1.526 (13)	C14—H14B	0.9800
N2—C15	1.458 (12)	C14—H14C	0.9800
C2—H2A	0.9900	C15—C16	1.416 (15)
C2—H2B	0.9900	C15—C20	1.402 (16)
C2—C3	1.521 (16)	C16—C17	1.402 (14)
C3—H3A	0.9900	C16—C21	1.492 (14)
C3—H3B	0.9900	C17—H17	0.9500
C3—C4	1.515 (15)	C17—C18	1.415 (16)
C4—H4A	0.9900	C18—C19	1.374 (16)
C4—H4B	0.9900	C18—C22	1.505 (14)
C4—C5	1.517 (14)	C19—H19	0.9500
C5—H5A	0.9900	C19—C20	1.383 (15)
C5—H5B	0.9900	C20—C23	1.504 (15)
C6—C7	1.407 (14)	C21—H21A	0.9800
C6—C11	1.398 (15)	C21—H21B	0.9800
C7—C8	1.377 (14)	C21—H21C	0.9800
C7—C12	1.505 (14)	C22—H22A	0.9800
C8—H8	0.9500	C22—H22B	0.9800
C8—C9	1.407 (15)	C22—H22C	0.9800
C9—C10	1.383 (16)	C23—H23A	0.9800
C9—C13	1.512 (16)	C23—H23B	0.9800
C10—H10	0.9500	C23—H23C	0.9800
C10—C11	1.394 (15)	I2—I3	3.0222 (11)
C11—C14	1.503 (14)	I3—I4	2.8492 (11)
C12—H12A	0.9800
C1—Se1—I1	106.5 (3)	C7—C12—H12C	109.5
C1—N1—C2	119.2 (8)	H12A—C12—H12B	109.5
C1—N1—C6	123.3 (8)	H12A—C12—H12C	109.5
C6—N1—C2	117.5 (8)	H12B—C12—H12C	109.5
C1—N2—C5	127.5 (9)	C9—C13—H13A	109.5
C1—N2—C15	119.9 (8)	C9—C13—H13B	109.5
C15—N2—C5	112.4 (8)	C9—C13—H13C	109.5
N1—C1—Se1	123.2 (7)	H13A—C13—H13B	109.5
N2—C1—Se1	113.4 (7)	H13A—C13—H13C	109.5
N2—C1—N1	123.4 (9)	H13B—C13—H13C	109.5
N1—C2—H2A	109.0	C11—C14—H14A	109.5
N1—C2—H2B	109.0	C11—C14—H14B	109.5
N1—C2—C3	112.9 (9)	C11—C14—H14C	109.5
H2A—C2—H2B	107.8	H14A—C14—H14B	109.5
C3—C2—H2A	109.0	H14A—C14—H14C	109.5
C3—C2—H2B	109.0	H14B—C14—H14C	109.5
C2—C3—H3A	109.1	C16—C15—N2	117.8 (9)
C2—C3—H3B	109.1	C20—C15—N2	119.2 (9)
H3A—C3—H3B	107.8	C20—C15—C16	123.0 (9)
C4—C3—C2	112.5 (9)	C15—C16—C21	121.6 (9)
C4—C3—H3A	109.1	C17—C16—C15	116.7 (9)
C4—C3—H3B	109.1	C17—C16—C21	121.6 (10)
C3—C4—H4A	109.0	C16—C17—H17	119.2
C3—C4—H4B	109.0	C16—C17—C18	121.6 (10)
C3—C4—C5	113.1 (9)	C18—C17—H17	119.2
H4A—C4—H4B	107.8	C17—C18—C22	118.7 (10)
C5—C4—H4A	109.0	C19—C18—C17	118.2 (10)
C5—C4—H4B	109.0	C19—C18—C22	123.1 (10)
N2—C5—H5A	108.5	C18—C19—H19	118.2
N2—C5—H5B	108.5	C18—C19—C20	123.6 (11)
C4—C5—N2	115.0 (9)	C20—C19—H19	118.2
C4—C5—H5A	108.5	C15—C20—C23	122.0 (9)
C4—C5—H5B	108.5	C19—C20—C15	116.9 (10)
H5A—C5—H5B	107.5	C19—C20—C23	121.1 (10)
C7—C6—N1	118.3 (9)	C16—C21—H21A	109.5
C11—C6—N1	119.6 (9)	C16—C21—H21B	109.5
C11—C6—C7	122.1 (9)	C16—C21—H21C	109.5
C6—C7—C12	123.5 (9)	H21A—C21—H21B	109.5
C8—C7—C6	117.8 (10)	H21A—C21—H21C	109.5
C8—C7—C12	118.7 (9)	H21B—C21—H21C	109.5
C7—C8—H8	118.9	C18—C22—H22A	109.5
C7—C8—C9	122.3 (10)	C18—C22—H22B	109.5
C9—C8—H8	118.9	C18—C22—H22C	109.5
C8—C9—C13	120.1 (10)	H22A—C22—H22B	109.5
C10—C9—C8	117.7 (10)	H22A—C22—H22C	109.5
C10—C9—C13	122.2 (10)	H22B—C22—H22C	109.5
C9—C10—H10	118.6	C20—C23—H23A	109.5
C9—C10—C11	122.8 (10)	C20—C23—H23B	109.5
C11—C10—H10	118.6	C20—C23—H23C	109.5
C6—C11—C14	123.7 (9)	H23A—C23—H23B	109.5
C10—C11—C6	117.3 (10)	H23A—C23—H23C	109.5
C10—C11—C14	118.9 (9)	H23B—C23—H23C	109.5
C7—C12—H12A	109.5	I4—I3—I2	176.12 (4)
C7—C12—H12B	109.5
N1—C2—C3—C4	53.7 (12)	C6—C7—C8—C9	0.0 (15)
N1—C6—C7—C8	−179.0 (9)	C7—C6—C11—C10	1.7 (15)
N1—C6—C7—C12	3.6 (15)	C7—C6—C11—C14	−176.9 (10)
N1—C6—C11—C10	179.0 (9)	C7—C8—C9—C10	1.5 (15)
N1—C6—C11—C14	0.4 (15)	C7—C8—C9—C13	−178.2 (9)
N2—C15—C16—C17	−179.9 (9)	C8—C9—C10—C11	−1.5 (15)
N2—C15—C16—C21	−3.3 (15)	C9—C10—C11—C6	−0.1 (15)
N2—C15—C20—C19	−179.4 (9)	C9—C10—C11—C14	178.6 (10)
N2—C15—C20—C23	−0.2 (15)	C11—C6—C7—C8	−1.7 (15)
C1—N1—C2—C3	−83.4 (12)	C11—C6—C7—C12	−179.1 (10)
C1—N1—C6—C7	−118.3 (11)	C12—C7—C8—C9	177.6 (10)
C1—N1—C6—C11	64.3 (13)	C13—C9—C10—C11	178.3 (9)
C1—N2—C5—C4	28.2 (15)	C15—N2—C1—Se1	13.1 (12)
C1—N2—C15—C16	87.2 (12)	C15—N2—C1—N1	−168.0 (9)
C1—N2—C15—C20	−93.2 (12)	C15—N2—C5—C4	−148.0 (9)
C2—N1—C1—Se1	−161.4 (7)	C15—C16—C17—C18	−0.1 (15)
C2—N1—C1—N2	19.7 (15)	C16—C15—C20—C19	0.2 (15)
C2—N1—C6—C7	62.5 (12)	C16—C15—C20—C23	179.4 (10)
C2—N1—C6—C11	−114.9 (11)	C16—C17—C18—C19	−1.2 (16)
C2—C3—C4—C5	31.2 (12)	C16—C17—C18—C22	178.9 (9)
C3—C4—C5—N2	−75.1 (11)	C17—C18—C19—C20	2.1 (16)
C5—N2—C1—Se1	−162.9 (8)	C18—C19—C20—C15	−1.6 (16)
C5—N2—C1—N1	16.0 (16)	C18—C19—C20—C23	179.2 (10)
C5—N2—C15—C16	−96.2 (11)	C20—C15—C16—C17	0.6 (15)
C5—N2—C15—C20	83.3 (11)	C20—C15—C16—C21	177.2 (10)
C6—N1—C1—Se1	19.4 (14)	C21—C16—C17—C18	−176.6 (10)
C6—N1—C1—N2	−159.4 (10)	C22—C18—C19—C20	−178.1 (10)
C6—N1—C2—C3	95.8 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···I3^i	0.99	3.24	4.029 (10)	138
C2—H2B···I4^i	0.99	3.12	3.823 (11)	129
C3—H3B···I2^ii	0.99	3.22	3.998 (11)	137
C5—H5B···Se1^iii	0.99	3.09	3.693 (11)	121

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z; (iii) x−1/2, −y+3/2, z−1/2.

(SDiazMesSeI_I3_DCM)

Crystal data

C23H30IN2Se·I3·CH2Cl2	Z = 2
Mr = 1005.97	F(000) = 940
Triclinic, P1	Dx = 2.129 Mg m^−3
a = 8.4541 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.5353 (4) Å	Cell parameters from 64752 reflections
c = 22.0045 (11) Å	θ = 2.4–29.6°
α = 93.258 (2)°	µ = 5.32 mm^−1
β = 90.198 (2)°	T = 100 K
γ = 98.032 (2)°	Plate, red
V = 1569.58 (13) Å^3	0.24 × 0.15 × 0.05 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	7994 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.038
φ and ω scans	θmax = 29.6°, θmin = 2.4°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −11→11
Tmin = 0.527, Tmax = 0.746	k = −11→11
64752 measured reflections	l = −30→30
8821 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.019	H-atom parameters constrained
wR(F^2) = 0.043	w = 1/[σ^2(Fo^2) + (0.0077P)^2 + 1.7629P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max = 0.004
8821 reflections	Δρmax = 0.81 e Å^−3
304 parameters	Δρmin = −0.88 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	1.08899 (2)	0.41978 (2)	0.70459 (2)	0.01695 (3)
I2	1.21875 (2)	0.08963 (2)	0.67867 (2)	0.02237 (4)
I3	1.31997 (2)	0.08657 (2)	0.80982 (2)	0.01745 (3)
I4	1.42535 (2)	0.08034 (2)	0.93236 (2)	0.02692 (4)
Se1	0.99525 (2)	0.69370 (2)	0.72771 (2)	0.01595 (4)
N1	0.7724 (2)	0.54815 (19)	0.81139 (8)	0.0131 (3)
N2	0.6632 (2)	0.6679 (2)	0.73064 (8)	0.0150 (3)
C1	0.7875 (2)	0.6272 (2)	0.76082 (9)	0.0133 (4)
C2	0.6158 (2)	0.4582 (2)	0.82727 (10)	0.0166 (4)
H2A	0.634451	0.373252	0.854154	0.020*
H2B	0.562633	0.407149	0.789611	0.020*
C3	0.5060 (3)	0.5616 (3)	0.85889 (11)	0.0220 (4)
H3A	0.550320	0.598557	0.899740	0.026*
H3B	0.400136	0.498399	0.864306	0.026*
C4	0.4862 (3)	0.7049 (3)	0.82250 (11)	0.0225 (5)
H4A	0.381050	0.738325	0.831890	0.027*
H4B	0.569619	0.793603	0.835772	0.027*
C5	0.4974 (3)	0.6740 (3)	0.75456 (10)	0.0207 (4)
H5A	0.430654	0.571824	0.742882	0.025*
H5B	0.451181	0.757966	0.734235	0.025*
C6	0.9038 (2)	0.5457 (2)	0.85400 (9)	0.0135 (4)
C7	0.9539 (2)	0.3996 (2)	0.86445 (9)	0.0135 (4)
C8	1.0733 (2)	0.3973 (2)	0.90838 (9)	0.0151 (4)
H8	1.108985	0.299323	0.915870	0.018*
C9	1.1414 (2)	0.5337 (3)	0.94140 (9)	0.0161 (4)
C10	1.0874 (3)	0.6762 (3)	0.93010 (10)	0.0178 (4)
H10	1.133794	0.770283	0.952279	0.021*
C11	0.9675 (3)	0.6854 (2)	0.88728 (9)	0.0162 (4)
C12	0.8835 (3)	0.2452 (2)	0.83186 (10)	0.0168 (4)
H12A	0.807145	0.185952	0.858473	0.025*
H12B	0.969092	0.182452	0.821294	0.025*
H12C	0.828454	0.266971	0.794638	0.025*
C13	1.2663 (3)	0.5267 (3)	0.98998 (10)	0.0217 (4)
H13A	1.214326	0.513026	1.029443	0.032*
H13B	1.341333	0.625372	0.991958	0.032*
H13C	1.324337	0.437012	0.980085	0.032*
C14	0.9079 (3)	0.8425 (3)	0.88093 (11)	0.0229 (5)
H14A	0.909002	0.866989	0.837946	0.034*
H14B	0.977424	0.925885	0.904497	0.034*
H14C	0.798613	0.836435	0.896212	0.034*
C15	0.6763 (2)	0.7079 (2)	0.66740 (9)	0.0147 (4)
C16	0.6542 (3)	0.5839 (3)	0.62244 (10)	0.0178 (4)
C17	0.6543 (3)	0.6254 (3)	0.56198 (10)	0.0233 (5)
H17	0.642023	0.543807	0.530408	0.028*
C18	0.6719 (3)	0.7830 (3)	0.54662 (10)	0.0241 (5)
C19	0.6949 (3)	0.9021 (3)	0.59294 (10)	0.0213 (4)
H19	0.709395	1.009704	0.582674	0.026*
C20	0.6971 (2)	0.8674 (2)	0.65402 (10)	0.0162 (4)
C21	0.6309 (3)	0.4128 (3)	0.63782 (11)	0.0247 (5)
H21A	0.714928	0.394842	0.666333	0.037*
H21B	0.636270	0.345259	0.600560	0.037*
H21C	0.526228	0.386796	0.656579	0.037*
C22	0.6606 (4)	0.8253 (4)	0.48136 (12)	0.0380 (6)
H22A	0.554214	0.853182	0.473341	0.057*
H22B	0.678532	0.734368	0.454306	0.057*
H22C	0.741732	0.915769	0.473972	0.057*
C23	0.7241 (3)	0.9986 (3)	0.70328 (10)	0.0214 (4)
H23A	0.628302	0.996965	0.728325	0.032*
H23B	0.746331	1.100933	0.684690	0.032*
H23C	0.815183	0.983355	0.728865	0.032*
Cl1	0.27587 (8)	0.70192 (9)	0.57406 (3)	0.03720 (15)
Cl2	0.04931 (9)	0.71889 (11)	0.47552 (3)	0.04679 (18)
C24	0.0769 (3)	0.7172 (4)	0.55546 (13)	0.0365 (6)
H24A	0.047093	0.815922	0.575214	0.044*
H24B	0.005871	0.626610	0.571156	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01424 (6)	0.02080 (7)	0.01537 (6)	0.00052 (5)	0.00161 (5)	0.00211 (5)
I2	0.03007 (8)	0.01919 (7)	0.01743 (7)	0.00196 (6)	0.00370 (6)	0.00084 (5)
I3	0.01655 (6)	0.01388 (6)	0.02183 (7)	0.00186 (5)	0.00191 (5)	0.00082 (5)
I4	0.03274 (8)	0.02312 (7)	0.02366 (8)	−0.00002 (6)	−0.00650 (6)	0.00070 (6)
Se1	0.01255 (9)	0.01629 (9)	0.01856 (10)	−0.00137 (7)	0.00119 (7)	0.00550 (8)
N1	0.0109 (7)	0.0130 (7)	0.0153 (8)	0.0003 (6)	0.0018 (6)	0.0036 (6)
N2	0.0137 (8)	0.0168 (8)	0.0147 (8)	0.0021 (6)	0.0011 (6)	0.0029 (6)
C1	0.0133 (9)	0.0105 (8)	0.0154 (9)	−0.0001 (7)	0.0006 (7)	−0.0002 (7)
C2	0.0141 (9)	0.0153 (9)	0.0203 (10)	−0.0008 (7)	0.0031 (8)	0.0067 (8)
C3	0.0182 (10)	0.0271 (11)	0.0221 (11)	0.0058 (9)	0.0064 (8)	0.0072 (9)
C4	0.0207 (11)	0.0252 (11)	0.0239 (11)	0.0092 (9)	0.0065 (9)	0.0052 (9)
C5	0.0148 (10)	0.0245 (11)	0.0244 (11)	0.0071 (8)	0.0013 (8)	0.0051 (9)
C6	0.0138 (9)	0.0150 (9)	0.0115 (9)	0.0006 (7)	0.0013 (7)	0.0025 (7)
C7	0.0152 (9)	0.0146 (9)	0.0110 (9)	0.0020 (7)	0.0027 (7)	0.0021 (7)
C8	0.0150 (9)	0.0180 (9)	0.0133 (9)	0.0049 (7)	0.0005 (7)	0.0032 (7)
C9	0.0129 (9)	0.0237 (10)	0.0112 (9)	0.0009 (8)	0.0028 (7)	0.0023 (8)
C10	0.0172 (10)	0.0180 (10)	0.0167 (10)	−0.0016 (8)	0.0010 (8)	−0.0023 (8)
C11	0.0188 (10)	0.0146 (9)	0.0152 (10)	0.0009 (8)	0.0016 (8)	0.0029 (7)
C12	0.0181 (10)	0.0140 (9)	0.0179 (10)	0.0016 (7)	−0.0002 (8)	0.0014 (7)
C13	0.0163 (10)	0.0343 (12)	0.0139 (10)	0.0019 (9)	−0.0015 (8)	0.0013 (9)
C14	0.0299 (12)	0.0147 (10)	0.0239 (11)	0.0034 (9)	−0.0033 (9)	−0.0006 (8)
C15	0.0142 (9)	0.0175 (9)	0.0125 (9)	0.0016 (7)	−0.0015 (7)	0.0029 (7)
C16	0.0156 (9)	0.0185 (10)	0.0184 (10)	0.0004 (8)	−0.0034 (8)	−0.0014 (8)
C17	0.0216 (11)	0.0300 (12)	0.0173 (11)	0.0031 (9)	−0.0045 (8)	−0.0045 (9)
C18	0.0214 (11)	0.0350 (13)	0.0161 (10)	0.0032 (9)	−0.0026 (8)	0.0052 (9)
C19	0.0218 (11)	0.0233 (11)	0.0195 (11)	0.0034 (9)	0.0008 (8)	0.0083 (8)
C20	0.0139 (9)	0.0188 (10)	0.0160 (10)	0.0029 (7)	−0.0015 (7)	0.0015 (8)
C21	0.0263 (12)	0.0178 (10)	0.0289 (12)	0.0006 (9)	−0.0035 (10)	−0.0019 (9)
C22	0.0455 (16)	0.0535 (18)	0.0165 (12)	0.0089 (14)	−0.0040 (11)	0.0094 (11)
C23	0.0262 (11)	0.0163 (10)	0.0219 (11)	0.0039 (8)	0.0009 (9)	0.0009 (8)
Cl1	0.0272 (3)	0.0408 (4)	0.0424 (4)	0.0028 (3)	0.0020 (3)	−0.0040 (3)
Cl2	0.0392 (4)	0.0684 (5)	0.0305 (4)	−0.0015 (4)	0.0049 (3)	0.0049 (3)
C24	0.0232 (12)	0.0535 (17)	0.0302 (14)	−0.0007 (12)	0.0038 (10)	−0.0056 (12)

Geometric parameters (Å, º)

I1—Se1	2.5959 (3)	C12—H12B	0.9800
I2—I3	3.0098 (2)	C12—H12C	0.9800
I3—I4	2.8428 (2)	C13—H13A	0.9800
Se1—C1	1.928 (2)	C13—H13B	0.9800
N1—C1	1.331 (3)	C13—H13C	0.9800
N1—C2	1.488 (3)	C14—H14A	0.9800
N1—C6	1.454 (3)	C14—H14B	0.9800
N2—C1	1.338 (3)	C14—H14C	0.9800
N2—C5	1.506 (3)	C15—C16	1.399 (3)
N2—C15	1.453 (3)	C15—C20	1.396 (3)
C2—H2A	0.9900	C16—C17	1.396 (3)
C2—H2B	0.9900	C16—C21	1.505 (3)
C2—C3	1.513 (3)	C17—H17	0.9500
C3—H3A	0.9900	C17—C18	1.394 (3)
C3—H3B	0.9900	C18—C19	1.391 (3)
C3—C4	1.527 (3)	C18—C22	1.506 (3)
C4—H4A	0.9900	C19—H19	0.9500
C4—H4B	0.9900	C19—C20	1.393 (3)
C4—C5	1.509 (3)	C20—C23	1.507 (3)
C5—H5A	0.9900	C21—H21A	0.9800
C5—H5B	0.9900	C21—H21B	0.9800
C6—C7	1.402 (3)	C21—H21C	0.9800
C6—C11	1.402 (3)	C22—H22A	0.9800
C7—C8	1.399 (3)	C22—H22B	0.9800
C7—C12	1.508 (3)	C22—H22C	0.9800
C8—H8	0.9500	C23—H23A	0.9800
C8—C9	1.389 (3)	C23—H23B	0.9800
C9—C10	1.392 (3)	C23—H23C	0.9800
C9—C13	1.510 (3)	Cl1—C24	1.754 (3)
C10—H10	0.9500	Cl2—C24	1.775 (3)
C10—C11	1.395 (3)	C24—H24A	0.9900
C11—C14	1.510 (3)	C24—H24B	0.9900
C12—H12A	0.9800
I4—I3—I2	178.081 (7)	H12A—C12—H12C	109.5
C1—Se1—I1	100.02 (6)	H12B—C12—H12C	109.5
C1—N1—C2	120.48 (17)	C9—C13—H13A	109.5
C1—N1—C6	122.97 (17)	C9—C13—H13B	109.5
C6—N1—C2	116.54 (16)	C9—C13—H13C	109.5
C1—N2—C5	126.83 (18)	H13A—C13—H13B	109.5
C1—N2—C15	121.19 (17)	H13A—C13—H13C	109.5
C15—N2—C5	111.95 (16)	H13B—C13—H13C	109.5
N1—C1—Se1	120.79 (14)	C11—C14—H14A	109.5
N1—C1—N2	123.24 (18)	C11—C14—H14B	109.5
N2—C1—Se1	115.96 (15)	C11—C14—H14C	109.5
N1—C2—H2A	109.0	H14A—C14—H14B	109.5
N1—C2—H2B	109.0	H14A—C14—H14C	109.5
N1—C2—C3	112.86 (17)	H14B—C14—H14C	109.5
H2A—C2—H2B	107.8	C16—C15—N2	118.03 (18)
C3—C2—H2A	109.0	C20—C15—N2	118.86 (18)
C3—C2—H2B	109.0	C20—C15—C16	122.89 (19)
C2—C3—H3A	109.3	C15—C16—C21	122.1 (2)
C2—C3—H3B	109.3	C17—C16—C15	117.1 (2)
C2—C3—C4	111.52 (18)	C17—C16—C21	120.8 (2)
H3A—C3—H3B	108.0	C16—C17—H17	119.1
C4—C3—H3A	109.3	C18—C17—C16	121.9 (2)
C4—C3—H3B	109.3	C18—C17—H17	119.1
C3—C4—H4A	108.8	C17—C18—C22	121.1 (2)
C3—C4—H4B	108.8	C19—C18—C17	118.8 (2)
H4A—C4—H4B	107.7	C19—C18—C22	120.0 (2)
C5—C4—C3	113.74 (19)	C18—C19—H19	119.2
C5—C4—H4A	108.8	C18—C19—C20	121.6 (2)
C5—C4—H4B	108.8	C20—C19—H19	119.2
N2—C5—C4	115.55 (18)	C15—C20—C23	121.82 (19)
N2—C5—H5A	108.4	C19—C20—C15	117.6 (2)
N2—C5—H5B	108.4	C19—C20—C23	120.6 (2)
C4—C5—H5A	108.4	C16—C21—H21A	109.5
C4—C5—H5B	108.4	C16—C21—H21B	109.5
H5A—C5—H5B	107.5	C16—C21—H21C	109.5
C7—C6—N1	118.44 (17)	H21A—C21—H21B	109.5
C11—C6—N1	119.68 (17)	H21A—C21—H21C	109.5
C11—C6—C7	121.64 (18)	H21B—C21—H21C	109.5
C6—C7—C12	123.53 (18)	C18—C22—H22A	109.5
C8—C7—C6	117.94 (18)	C18—C22—H22B	109.5
C8—C7—C12	118.52 (18)	C18—C22—H22C	109.5
C7—C8—H8	119.0	H22A—C22—H22B	109.5
C9—C8—C7	122.01 (19)	H22A—C22—H22C	109.5
C9—C8—H8	119.0	H22B—C22—H22C	109.5
C8—C9—C10	118.34 (19)	C20—C23—H23A	109.5
C8—C9—C13	120.82 (19)	C20—C23—H23B	109.5
C10—C9—C13	120.80 (19)	C20—C23—H23C	109.5
C9—C10—H10	118.9	H23A—C23—H23B	109.5
C9—C10—C11	122.14 (19)	H23A—C23—H23C	109.5
C11—C10—H10	118.9	H23B—C23—H23C	109.5
C6—C11—C14	123.29 (19)	Cl1—C24—Cl2	111.17 (15)
C10—C11—C6	117.91 (19)	Cl1—C24—H24A	109.4
C10—C11—C14	118.75 (19)	Cl1—C24—H24B	109.4
C7—C12—H12A	109.5	Cl2—C24—H24A	109.4
C7—C12—H12B	109.5	Cl2—C24—H24B	109.4
C7—C12—H12C	109.5	H24A—C24—H24B	108.0
H12A—C12—H12B	109.5
N1—C2—C3—C4	52.9 (3)	C6—C7—C8—C9	0.3 (3)
N1—C6—C7—C8	−175.98 (18)	C7—C6—C11—C10	2.2 (3)
N1—C6—C7—C12	2.7 (3)	C7—C6—C11—C14	−175.1 (2)
N1—C6—C11—C10	176.54 (18)	C7—C8—C9—C10	0.3 (3)
N1—C6—C11—C14	−0.7 (3)	C7—C8—C9—C13	177.99 (19)
N2—C15—C16—C17	174.89 (19)	C8—C9—C10—C11	0.4 (3)
N2—C15—C16—C21	−5.0 (3)	C9—C10—C11—C6	−1.6 (3)
N2—C15—C20—C19	−174.33 (18)	C9—C10—C11—C14	175.8 (2)
N2—C15—C20—C23	6.8 (3)	C11—C6—C7—C8	−1.5 (3)
C1—N1—C2—C3	−82.9 (2)	C11—C6—C7—C12	177.10 (19)
C1—N1—C6—C7	−118.8 (2)	C12—C7—C8—C9	−178.42 (19)
C1—N1—C6—C11	66.7 (3)	C13—C9—C10—C11	−177.3 (2)
C1—N2—C5—C4	27.3 (3)	C15—N2—C1—Se1	20.8 (2)
C1—N2—C15—C16	84.3 (2)	C15—N2—C1—N1	−160.43 (19)
C1—N2—C15—C20	−100.9 (2)	C15—N2—C5—C4	−154.56 (18)
C2—N1—C1—Se1	−162.61 (14)	C15—C16—C17—C18	−1.5 (3)
C2—N1—C1—N2	18.7 (3)	C16—C15—C20—C19	0.2 (3)
C2—N1—C6—C7	62.0 (2)	C16—C15—C20—C23	−178.7 (2)
C2—N1—C6—C11	−112.6 (2)	C16—C17—C18—C19	2.0 (4)
C2—C3—C4—C5	31.2 (3)	C16—C17—C18—C22	−175.8 (2)
C3—C4—C5—N2	−75.4 (3)	C17—C18—C19—C20	−1.4 (4)
C5—N2—C1—Se1	−161.26 (16)	C18—C19—C20—C15	0.4 (3)
C5—N2—C1—N1	17.5 (3)	C18—C19—C20—C23	179.3 (2)
C5—N2—C15—C16	−93.9 (2)	C20—C15—C16—C17	0.3 (3)
C5—N2—C15—C20	80.8 (2)	C20—C15—C16—C21	−179.6 (2)
C6—N1—C1—Se1	18.2 (3)	C21—C16—C17—C18	178.5 (2)
C6—N1—C1—N2	−160.53 (19)	C22—C18—C19—C20	176.4 (2)
C6—N1—C2—C3	96.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···I3^i	0.99	3.24	3.755 (2)	114
C4—H4A···I3^ii	0.99	3.15	3.748 (2)	120
C5—H5A···I1^i	0.99	3.09	3.930 (2)	144

Symmetry codes: (i) x−1, y, z; (ii) x−1, y+1, z.

(SDiazMesSeDMK_I3_I2)

Crystal data

3.333(I1.5)·C26H35N2OSe	F(000) = 4096
Mr = 1105.02	Dx = 2.214 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.2501 (6) Å	Cell parameters from 9214 reflections
b = 11.0708 (6) Å	θ = 2.4–26.1°
c = 45.509 (3) Å	µ = 5.81 mm^−1
β = 96.722 (2)°	T = 100 K
V = 6629.7 (6) Å^3	Plate, red
Z = 8	0.17 × 0.15 × 0.05 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	5737 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.041
φ and ω scans	θmax = 26.2°, θmin = 2.4°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −16→15
Tmin = 0.561, Tmax = 0.745	k = −13→13
46614 measured reflections	l = −56→56
6580 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.018P)^2 + 376.8008P] where P = (Fo^2 + 2Fc^2)/3
6580 reflections	(Δ/σ)max = 0.001
325 parameters	Δρmax = 4.07 e Å^−3
0 restraints	Δρmin = −3.13 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.500000	0.500000	0.500000	0.0499 (3)
I2	0.59217 (7)	0.28252 (10)	0.48034 (2)	0.0629 (3)
I3	0.43289 (6)	0.24158 (7)	0.42050 (2)	0.0447 (2)
I4	0.30499 (7)	0.20343 (7)	0.36906 (2)	0.0472 (2)
I5	0.14036 (7)	0.19618 (11)	0.30440 (2)	0.0644 (3)
I6	0.000000	0.19062 (9)	0.250000	0.0399 (3)
Se1	0.43060 (8)	0.85323 (11)	0.36915 (2)	0.0365 (3)
O1	0.5273 (8)	1.0240 (10)	0.33671 (19)	0.073 (4)
N1	0.2752 (7)	0.6675 (9)	0.36531 (18)	0.044 (3)
N2	0.3725 (5)	0.7013 (6)	0.41039 (15)	0.0162 (14)
C1	0.3465 (6)	0.7280 (8)	0.38187 (19)	0.0193 (17)
C2	0.3169 (8)	0.6205 (10)	0.4295 (2)	0.034 (2)
H2A	0.331984	0.646455	0.450415	0.041*
H2B	0.341989	0.536748	0.428052	0.041*
C3	0.2019 (10)	0.6222 (13)	0.4209 (3)	0.053 (3)
H3A	0.179667	0.705221	0.415208	0.063*
H3B	0.167092	0.597485	0.438038	0.063*
C4	0.1723 (7)	0.5353 (9)	0.3947 (2)	0.028 (2)
H4A	0.164383	0.452561	0.402371	0.033*
H4B	0.106332	0.560557	0.384022	0.033*
C5	0.2511 (10)	0.5353 (10)	0.3741 (3)	0.041 (3)
H5A	0.226572	0.488629	0.356082	0.050*
H5B	0.313692	0.496215	0.383618	0.050*
C6	0.4604 (6)	0.7580 (8)	0.42725 (18)	0.0182 (17)
C7	0.4461 (7)	0.8626 (8)	0.44333 (18)	0.0201 (18)
C8	0.5304 (7)	0.9104 (9)	0.46074 (19)	0.026 (2)
H8	0.522867	0.982926	0.471410	0.031*
C9	0.6241 (7)	0.8553 (9)	0.46289 (19)	0.025 (2)
C10	0.6357 (7)	0.7511 (9)	0.44608 (19)	0.0232 (19)
H10	0.700970	0.715002	0.446795	0.028*
C11	0.5552 (7)	0.6996 (8)	0.4285 (2)	0.0220 (18)
C12	0.3427 (8)	0.9228 (9)	0.4419 (2)	0.033 (2)
H12A	0.315041	0.934670	0.421196	0.049*
H12B	0.349752	1.001268	0.451932	0.049*
H12C	0.296589	0.871426	0.451735	0.049*
C13	0.7122 (8)	0.9065 (10)	0.4830 (2)	0.036 (2)
H13A	0.710490	0.875263	0.503125	0.054*
H13B	0.707292	0.994812	0.483268	0.054*
H13C	0.776202	0.882702	0.475830	0.054*
C14	0.5692 (8)	0.5867 (9)	0.4110 (2)	0.031 (2)
H14A	0.523956	0.523247	0.416864	0.047*
H14B	0.639883	0.559504	0.414886	0.047*
H14C	0.552801	0.603754	0.389857	0.047*
C15	0.2352 (7)	0.7035 (10)	0.3357 (2)	0.029 (2)
C16	0.1632 (7)	0.7955 (11)	0.3313 (2)	0.032 (2)
C17	0.1323 (7)	0.8316 (10)	0.3026 (2)	0.030 (2)
H17	0.085051	0.896115	0.299273	0.036*
C18	0.1684 (7)	0.7761 (8)	0.27840 (19)	0.0214 (18)
C19	0.2352 (7)	0.6804 (8)	0.2838 (2)	0.0231 (19)
H19	0.257980	0.639172	0.267535	0.028*
C20	0.2703 (7)	0.6424 (8)	0.3125 (2)	0.027 (2)
C21	0.1246 (9)	0.8563 (15)	0.3571 (3)	0.059 (4)
H21A	0.180705	0.898396	0.368784	0.088*
H21B	0.095920	0.795797	0.369449	0.088*
H21C	0.071839	0.914792	0.349916	0.088*
C22	0.1392 (9)	0.8227 (10)	0.2475 (2)	0.037 (2)
H22A	0.080959	0.776817	0.238038	0.055*
H22B	0.196765	0.813270	0.235929	0.055*
H22C	0.121055	0.908338	0.248265	0.055*
C23	0.3506 (10)	0.5428 (10)	0.3162 (3)	0.044 (3)
H23A	0.319665	0.467816	0.322295	0.066*
H23B	0.405642	0.566869	0.331384	0.066*
H23C	0.378158	0.529814	0.297399	0.066*
C24	0.3949 (8)	0.8837 (9)	0.3274 (2)	0.029 (2)
H24A	0.403421	0.809457	0.315766	0.035*
H24B	0.323303	0.910506	0.323420	0.035*
C25	0.4656 (7)	0.9816 (9)	0.3190 (2)	0.027 (2)
C26	0.4475 (10)	1.0260 (11)	0.2879 (2)	0.045 (3)
H26A	0.382220	1.068489	0.284851	0.068*
H26B	0.446176	0.957286	0.274273	0.068*
H26C	0.502186	1.081401	0.284099	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0343 (5)	0.0785 (8)	0.0324 (5)	−0.0317 (6)	−0.0153 (4)	0.0298 (5)
I2	0.0543 (5)	0.0807 (7)	0.0518 (5)	−0.0249 (5)	−0.0017 (4)	0.0244 (5)
I3	0.0446 (4)	0.0407 (4)	0.0521 (5)	−0.0099 (3)	0.0192 (4)	0.0084 (3)
I4	0.0676 (5)	0.0244 (4)	0.0506 (5)	−0.0038 (4)	0.0108 (4)	−0.0003 (3)
I5	0.0545 (5)	0.0851 (7)	0.0531 (5)	0.0014 (5)	0.0039 (4)	0.0054 (5)
I6	0.0437 (6)	0.0291 (5)	0.0498 (6)	0.000	0.0178 (5)	0.000
Se1	0.0389 (6)	0.0451 (6)	0.0225 (5)	−0.0279 (5)	−0.0089 (4)	0.0138 (4)
O1	0.079 (7)	0.092 (8)	0.042 (5)	−0.069 (6)	−0.022 (5)	0.028 (5)
N1	0.049 (6)	0.058 (6)	0.021 (4)	−0.043 (5)	−0.015 (4)	0.017 (4)
N2	0.015 (3)	0.017 (3)	0.015 (3)	−0.008 (3)	−0.003 (3)	0.001 (3)
C1	0.021 (4)	0.020 (4)	0.016 (4)	−0.001 (4)	0.001 (3)	−0.001 (3)
C2	0.036 (6)	0.043 (6)	0.021 (5)	−0.019 (5)	−0.008 (4)	0.012 (4)
C3	0.055 (8)	0.061 (9)	0.043 (7)	−0.022 (7)	0.009 (6)	0.002 (6)
C4	0.028 (5)	0.030 (5)	0.026 (5)	−0.012 (4)	0.004 (4)	0.002 (4)
C5	0.055 (7)	0.028 (6)	0.039 (6)	−0.008 (5)	0.000 (5)	−0.002 (5)
C6	0.015 (4)	0.021 (4)	0.017 (4)	−0.007 (3)	−0.006 (3)	0.002 (3)
C7	0.023 (4)	0.022 (4)	0.015 (4)	−0.002 (4)	0.004 (3)	−0.002 (3)
C8	0.034 (5)	0.031 (5)	0.012 (4)	−0.017 (4)	0.004 (4)	−0.002 (4)
C9	0.030 (5)	0.031 (5)	0.012 (4)	−0.012 (4)	−0.004 (3)	0.005 (4)
C10	0.019 (4)	0.029 (5)	0.021 (4)	−0.003 (4)	−0.003 (3)	0.006 (4)
C11	0.023 (4)	0.022 (4)	0.022 (4)	−0.004 (4)	0.003 (4)	0.007 (4)
C12	0.031 (5)	0.024 (5)	0.045 (6)	−0.003 (4)	0.010 (5)	−0.008 (4)
C13	0.040 (6)	0.035 (6)	0.031 (5)	−0.016 (5)	−0.008 (5)	−0.002 (5)
C14	0.027 (5)	0.026 (5)	0.039 (6)	−0.002 (4)	0.001 (4)	−0.002 (4)
C15	0.029 (5)	0.041 (6)	0.015 (4)	−0.019 (5)	−0.004 (4)	0.008 (4)
C16	0.026 (5)	0.050 (7)	0.022 (5)	−0.019 (5)	0.008 (4)	−0.010 (5)
C17	0.023 (5)	0.032 (5)	0.035 (5)	−0.004 (4)	−0.001 (4)	−0.004 (4)
C18	0.025 (5)	0.021 (5)	0.018 (4)	−0.007 (4)	0.004 (3)	0.001 (3)
C19	0.025 (5)	0.022 (5)	0.021 (4)	−0.005 (4)	−0.004 (4)	−0.002 (4)
C20	0.029 (5)	0.019 (5)	0.030 (5)	−0.010 (4)	−0.009 (4)	0.005 (4)
C21	0.034 (6)	0.102 (12)	0.041 (7)	−0.010 (7)	0.008 (5)	−0.031 (7)
C22	0.047 (6)	0.041 (6)	0.019 (5)	−0.003 (5)	−0.007 (4)	0.010 (4)
C23	0.059 (8)	0.024 (5)	0.045 (7)	0.002 (5)	−0.017 (6)	0.002 (5)
C24	0.034 (5)	0.034 (5)	0.017 (4)	−0.017 (4)	−0.007 (4)	0.007 (4)
C25	0.026 (5)	0.029 (5)	0.027 (5)	−0.012 (4)	0.004 (4)	0.002 (4)
C26	0.065 (8)	0.041 (7)	0.029 (6)	−0.022 (6)	0.002 (5)	0.009 (5)

Geometric parameters (Å, º)

I1—I2^i	2.8887 (12)	C12—H12B	0.9800
I1—I2	2.8887 (12)	C12—H12C	0.9800
I3—I4	2.7570 (13)	C13—H13A	0.9800
I5—I6	2.9180 (10)	C13—H13B	0.9800
Se1—C1	1.911 (9)	C13—H13C	0.9800
Se1—C24	1.935 (9)	C14—H14A	0.9800
O1—C25	1.177 (12)	C14—H14B	0.9800
N1—C1	1.319 (12)	C14—H14C	0.9800
N1—C5	1.560 (14)	C15—C16	1.393 (16)
N1—C15	1.446 (12)	C15—C20	1.381 (15)
N2—C1	1.337 (11)	C16—C17	1.383 (14)
N2—C2	1.501 (11)	C16—C21	1.492 (15)
N2—C6	1.459 (10)	C17—H17	0.9500
C2—H2A	0.9900	C17—C18	1.395 (13)
C2—H2B	0.9900	C18—C19	1.384 (13)
C2—C3	1.529 (16)	C18—C22	1.507 (12)
C3—H3A	0.9900	C19—H19	0.9500
C3—H3B	0.9900	C19—C20	1.396 (13)
C3—C4	1.545 (16)	C20—C23	1.528 (15)
C4—H4A	0.9900	C21—H21A	0.9800
C4—H4B	0.9900	C21—H21B	0.9800
C4—C5	1.485 (15)	C21—H21C	0.9800
C5—H5A	0.9900	C22—H22A	0.9800
C5—H5B	0.9900	C22—H22B	0.9800
C6—C7	1.395 (12)	C22—H22C	0.9800
C6—C11	1.408 (13)	C23—H23A	0.9800
C7—C8	1.396 (12)	C23—H23B	0.9800
C7—C12	1.518 (13)	C23—H23C	0.9800
C8—H8	0.9500	C24—H24A	0.9900
C8—C9	1.377 (14)	C24—H24B	0.9900
C9—C10	1.402 (14)	C24—C25	1.510 (12)
C9—C13	1.508 (13)	C25—C26	1.492 (14)
C10—H10	0.9500	C26—H26A	0.9800
C10—C11	1.379 (13)	C26—H26B	0.9800
C11—C14	1.507 (13)	C26—H26C	0.9800
C12—H12A	0.9800
I2^i—I1—I2	180.00 (4)	C9—C13—H13C	109.5
I5^ii—I6—I5	177.58 (6)	H13A—C13—H13B	109.5
C1—Se1—C24	109.9 (4)	H13A—C13—H13C	109.5
C1—N1—C5	119.0 (8)	H13B—C13—H13C	109.5
C1—N1—C15	123.6 (8)	C11—C14—H14A	109.5
C15—N1—C5	115.6 (8)	C11—C14—H14B	109.5
C1—N2—C2	127.4 (7)	C11—C14—H14C	109.5
C1—N2—C6	121.0 (7)	H14A—C14—H14B	109.5
C6—N2—C2	111.5 (7)	H14A—C14—H14C	109.5
N1—C1—Se1	126.8 (7)	H14B—C14—H14C	109.5
N1—C1—N2	121.9 (8)	C16—C15—N1	120.2 (10)
N2—C1—Se1	111.2 (6)	C20—C15—N1	117.3 (10)
N2—C2—H2A	109.1	C20—C15—C16	122.5 (9)
N2—C2—H2B	109.1	C15—C16—C21	120.7 (10)
N2—C2—C3	112.7 (8)	C17—C16—C15	117.8 (9)
H2A—C2—H2B	107.8	C17—C16—C21	121.4 (11)
C3—C2—H2A	109.1	C16—C17—H17	119.0
C3—C2—H2B	109.1	C16—C17—C18	121.9 (10)
C2—C3—H3A	109.6	C18—C17—H17	119.0
C2—C3—H3B	109.6	C17—C18—C22	120.9 (9)
C2—C3—C4	110.2 (11)	C19—C18—C17	117.9 (9)
H3A—C3—H3B	108.1	C19—C18—C22	121.2 (9)
C4—C3—H3A	109.6	C18—C19—H19	118.9
C4—C3—H3B	109.6	C18—C19—C20	122.3 (9)
C3—C4—H4A	109.5	C20—C19—H19	118.9
C3—C4—H4B	109.5	C15—C20—C19	117.4 (9)
H4A—C4—H4B	108.1	C15—C20—C23	124.1 (9)
C5—C4—C3	110.8 (9)	C19—C20—C23	118.3 (9)
C5—C4—H4A	109.5	C16—C21—H21A	109.5
C5—C4—H4B	109.5	C16—C21—H21B	109.5
N1—C5—H5A	109.7	C16—C21—H21C	109.5
N1—C5—H5B	109.7	H21A—C21—H21B	109.5
C4—C5—N1	110.0 (9)	H21A—C21—H21C	109.5
C4—C5—H5A	109.7	H21B—C21—H21C	109.5
C4—C5—H5B	109.7	C18—C22—H22A	109.5
H5A—C5—H5B	108.2	C18—C22—H22B	109.5
C7—C6—N2	119.0 (8)	C18—C22—H22C	109.5
C7—C6—C11	122.3 (8)	H22A—C22—H22B	109.5
C11—C6—N2	118.5 (8)	H22A—C22—H22C	109.5
C6—C7—C8	117.6 (8)	H22B—C22—H22C	109.5
C6—C7—C12	121.3 (8)	C20—C23—H23A	109.5
C8—C7—C12	121.1 (8)	C20—C23—H23B	109.5
C7—C8—H8	119.1	C20—C23—H23C	109.5
C9—C8—C7	121.9 (9)	H23A—C23—H23B	109.5
C9—C8—H8	119.1	H23A—C23—H23C	109.5
C8—C9—C10	118.7 (8)	H23B—C23—H23C	109.5
C8—C9—C13	120.3 (9)	Se1—C24—H24A	110.4
C10—C9—C13	121.0 (9)	Se1—C24—H24B	110.4
C9—C10—H10	119.0	H24A—C24—H24B	108.6
C11—C10—C9	122.0 (9)	C25—C24—Se1	106.5 (6)
C11—C10—H10	119.0	C25—C24—H24A	110.4
C6—C11—C14	121.6 (8)	C25—C24—H24B	110.4
C10—C11—C6	117.4 (9)	O1—C25—C24	121.2 (9)
C10—C11—C14	121.0 (9)	O1—C25—C26	122.6 (9)
C7—C12—H12A	109.5	C26—C25—C24	116.1 (8)
C7—C12—H12B	109.5	C25—C26—H26A	109.5
C7—C12—H12C	109.5	C25—C26—H26B	109.5
H12A—C12—H12B	109.5	C25—C26—H26C	109.5
H12A—C12—H12C	109.5	H26A—C26—H26B	109.5
H12B—C12—H12C	109.5	H26A—C26—H26C	109.5
C9—C13—H13A	109.5	H26B—C26—H26C	109.5
C9—C13—H13B	109.5
Se1—C24—C25—O1	−0.2 (14)	C6—N2—C2—C3	144.5 (9)
Se1—C24—C25—C26	−176.1 (8)	C6—C7—C8—C9	−1.9 (13)
N1—C15—C16—C17	175.9 (9)	C7—C6—C11—C10	−1.3 (13)
N1—C15—C16—C21	−1.3 (15)	C7—C6—C11—C14	−180.0 (8)
N1—C15—C20—C19	−177.2 (8)	C7—C8—C9—C10	2.7 (13)
N1—C15—C20—C23	−2.0 (14)	C7—C8—C9—C13	−177.1 (9)
N2—C2—C3—C4	82.5 (12)	C8—C9—C10—C11	−2.9 (13)
N2—C6—C7—C8	176.0 (8)	C9—C10—C11—C6	2.1 (13)
N2—C6—C7—C12	−4.2 (13)	C9—C10—C11—C14	−179.1 (8)
N2—C6—C11—C10	−176.1 (8)	C11—C6—C7—C8	1.2 (13)
N2—C6—C11—C14	5.2 (12)	C11—C6—C7—C12	−179.0 (9)
C1—N1—C5—C4	88.7 (13)	C12—C7—C8—C9	178.3 (9)
C1—N1—C15—C16	−79.1 (14)	C13—C9—C10—C11	177.0 (9)
C1—N1—C15—C20	101.6 (13)	C15—N1—C1—Se1	−13.0 (17)
C1—N2—C2—C3	−31.8 (15)	C15—N1—C1—N2	171.2 (10)
C1—N2—C6—C7	93.2 (10)	C15—N1—C5—C4	−106.0 (11)
C1—N2—C6—C11	−91.8 (10)	C15—C16—C17—C18	2.2 (14)
C2—N2—C1—Se1	171.3 (8)	C16—C15—C20—C19	3.5 (14)
C2—N2—C1—N1	−12.4 (15)	C16—C15—C20—C23	178.8 (10)
C2—N2—C6—C7	−83.4 (10)	C16—C17—C18—C19	1.5 (14)
C2—N2—C6—C11	91.6 (10)	C16—C17—C18—C22	−175.7 (9)
C2—C3—C4—C5	−35.6 (13)	C17—C18—C19—C20	−2.9 (14)
C3—C4—C5—N1	−51.3 (12)	C18—C19—C20—C15	0.5 (14)
C5—N1—C1—Se1	151.0 (8)	C18—C19—C20—C23	−175.0 (9)
C5—N1—C1—N2	−24.8 (15)	C20—C15—C16—C17	−4.9 (14)
C5—N1—C15—C16	116.4 (11)	C20—C15—C16—C21	177.9 (10)
C5—N1—C15—C20	−62.9 (12)	C21—C16—C17—C18	179.5 (10)
C6—N2—C1—Se1	−4.7 (10)	C22—C18—C19—C20	174.2 (9)
C6—N2—C1—N1	171.7 (9)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···I2^i	0.99	3.29	4.274 (10)	173
C3—H3B···I2^iii	0.99	3.06	3.674 (14)	122
C4—H4B···O1^iv	0.99	2.32	3.081 (13)	133
C26—H26B···I6^v	0.98	3.26	4.186 (13)	158

Symmetry codes: (i) −x+1, −y+1, −z+1; (iii) x−1/2, y+1/2, z; (iv) x−1/2, y−1/2, z; (v) x+1/2, y+1/2, z.

(SDiazMesSMIBK_I3)

Crystal data

I3·C29H41N2OS	Z = 2
Mr = 846.40	F(000) = 824
Triclinic, P1	Dx = 1.726 Mg m^−3
a = 8.7838 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.2194 (15) Å	Cell parameters from 9680 reflections
c = 15.1418 (15) Å	θ = 2.6–29.2°
α = 63.522 (3)°	µ = 2.97 mm^−1
β = 74.494 (4)°	T = 100 K
γ = 80.494 (4)°	Block, red
V = 1628.9 (3) Å^3	0.11 × 0.09 × 0.08 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	6624 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.052
φ and ω scans	θmax = 29.2°, θmin = 2.4°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −12→12
Tmin = 0.645, Tmax = 0.746	k = −19→19
60178 measured reflections	l = −20→20
8827 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.069	w = 1/[σ^2(Fo^2) + 4.6197P] where P = (Fo^2 + 2Fc^2)/3
S = 1.20	(Δ/σ)max = 0.001
8827 reflections	Δρmax = 2.75 e Å^−3
333 parameters	Δρmin = −0.92 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.88921 (3)	0.38632 (2)	0.09024 (2)	0.02408 (6)
I2	0.72699 (3)	0.19081 (2)	0.17581 (2)	0.01934 (5)
I3	0.56631 (3)	−0.00606 (2)	0.26107 (2)	0.03233 (7)
S1	0.05667 (10)	0.46475 (7)	0.36526 (6)	0.01818 (17)
O1	−0.2113 (3)	0.5914 (2)	0.3362 (2)	0.0295 (6)
N1	0.2562 (3)	0.3008 (2)	0.4062 (2)	0.0158 (5)
N2	0.3781 (3)	0.4598 (2)	0.2983 (2)	0.0151 (5)
C1	0.2498 (4)	0.4050 (3)	0.3507 (2)	0.0160 (6)
C2	0.5358 (4)	0.4062 (3)	0.2800 (3)	0.0187 (7)
H2A	0.606210	0.456891	0.220838	0.022*
H2B	0.523951	0.348077	0.263697	0.022*
C3	0.6117 (4)	0.3626 (3)	0.3700 (3)	0.0200 (7)
H3A	0.641039	0.421462	0.379077	0.024*
H3B	0.709748	0.320643	0.357020	0.024*
C4	0.5003 (4)	0.2931 (3)	0.4671 (3)	0.0202 (7)
H4A	0.563987	0.241732	0.514877	0.024*
H4B	0.433992	0.337620	0.499304	0.024*
C5	0.3934 (4)	0.2340 (3)	0.4472 (3)	0.0178 (7)
H5A	0.456766	0.206050	0.398427	0.021*
H5B	0.353008	0.173277	0.511080	0.021*
C6	0.3726 (4)	0.5737 (3)	0.2502 (2)	0.0151 (6)
C7	0.3515 (4)	0.6310 (3)	0.3078 (2)	0.0153 (6)
C8	0.3463 (4)	0.7401 (3)	0.2572 (3)	0.0195 (7)
H8	0.332101	0.780318	0.295049	0.023*
C9	0.3611 (4)	0.7927 (3)	0.1525 (3)	0.0192 (7)
C10	0.3879 (4)	0.7326 (3)	0.0981 (3)	0.0202 (7)
H10	0.401750	0.767318	0.026604	0.024*
C11	0.3952 (4)	0.6237 (3)	0.1443 (2)	0.0170 (6)
C12	0.3351 (4)	0.5792 (3)	0.4206 (3)	0.0224 (7)
H12A	0.258625	0.524235	0.451106	0.034*
H12B	0.298035	0.631814	0.447862	0.034*
H12C	0.438003	0.547626	0.436287	0.034*
C13	0.3458 (5)	0.9107 (3)	0.1011 (3)	0.0294 (9)
H13A	0.242098	0.935408	0.129688	0.044*
H13B	0.356252	0.933494	0.028483	0.044*
H13C	0.429237	0.940171	0.111580	0.044*
C14	0.4249 (4)	0.5623 (3)	0.0809 (3)	0.0238 (8)
H14A	0.538434	0.544417	0.064635	0.036*
H14B	0.388198	0.605143	0.018136	0.036*
H14C	0.367288	0.497542	0.118780	0.036*
C15	0.1242 (4)	0.2398 (3)	0.4238 (3)	0.0171 (7)
C16	0.0226 (4)	0.2008 (3)	0.5195 (3)	0.0184 (7)
C17	−0.0977 (4)	0.1388 (3)	0.5347 (3)	0.0184 (7)
H17	−0.168882	0.111907	0.598784	0.022*
C18	−0.1165 (4)	0.1151 (3)	0.4582 (3)	0.0200 (7)
C19	−0.0101 (4)	0.1540 (3)	0.3647 (3)	0.0202 (7)
H19	−0.021012	0.137411	0.312567	0.024*
C20	0.1119 (4)	0.2167 (3)	0.3459 (3)	0.0179 (7)
C21	0.0412 (4)	0.2253 (3)	0.6031 (3)	0.0242 (8)
H21A	−0.046736	0.197407	0.661588	0.036*
H21B	0.040869	0.301733	0.579334	0.036*
H21C	0.141434	0.192831	0.622710	0.036*
C22	−0.2460 (4)	0.0465 (3)	0.4764 (3)	0.0231 (7)
H22A	−0.203543	−0.026327	0.494570	0.035*
H22B	−0.286148	0.071610	0.414741	0.035*
H22C	−0.332269	0.049727	0.531638	0.035*
C23	0.2274 (4)	0.2545 (3)	0.2448 (3)	0.0226 (7)
H23A	0.214982	0.331255	0.209556	0.034*
H23B	0.206492	0.222537	0.203951	0.034*
H23C	0.335589	0.234230	0.255129	0.034*
C24	0.0261 (4)	0.5487 (3)	0.2388 (3)	0.0241 (8)
H24A	0.107782	0.601425	0.201279	0.029*
H24B	0.031337	0.506312	0.200911	0.029*
C25	−0.1369 (4)	0.6023 (3)	0.2527 (3)	0.0206 (7)
C26	−0.1986 (4)	0.6679 (3)	0.1584 (3)	0.0253 (8)
H26A	−0.306725	0.696259	0.177615	0.030*
H26B	−0.206246	0.621959	0.126399	0.030*
C27	−0.0964 (4)	0.7601 (3)	0.0801 (3)	0.0228 (7)
H27	0.009408	0.730610	0.055934	0.027*
C28	−0.1738 (5)	0.8212 (4)	−0.0097 (3)	0.0357 (10)
H28A	−0.188598	0.773501	−0.037240	0.053*
H28B	−0.105834	0.877263	−0.062013	0.053*
H28C	−0.276741	0.852152	0.012194	0.053*
C29	−0.0716 (6)	0.8313 (4)	0.1254 (4)	0.0385 (10)
H29A	−0.174440	0.859613	0.151075	0.058*
H29B	−0.007244	0.889470	0.073204	0.058*
H29C	−0.017272	0.790800	0.180959	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02009 (11)	0.02643 (13)	0.02587 (12)	−0.00218 (9)	−0.00205 (9)	−0.01254 (10)
I2	0.01807 (10)	0.02349 (12)	0.01696 (10)	0.00023 (8)	−0.00447 (8)	−0.00909 (9)
I3	0.03382 (14)	0.02925 (14)	0.03432 (14)	−0.00730 (11)	−0.00552 (11)	−0.01298 (12)
S1	0.0152 (4)	0.0163 (4)	0.0195 (4)	0.0007 (3)	−0.0043 (3)	−0.0048 (3)
O1	0.0204 (13)	0.0303 (15)	0.0268 (14)	0.0029 (11)	−0.0008 (11)	−0.0064 (12)
N1	0.0140 (13)	0.0140 (13)	0.0205 (14)	−0.0013 (10)	−0.0065 (11)	−0.0067 (11)
N2	0.0142 (13)	0.0135 (13)	0.0182 (13)	−0.0003 (10)	−0.0037 (11)	−0.0073 (11)
C1	0.0185 (16)	0.0162 (16)	0.0158 (15)	0.0021 (12)	−0.0058 (12)	−0.0087 (13)
C2	0.0161 (16)	0.0189 (17)	0.0195 (16)	0.0011 (13)	−0.0021 (13)	−0.0083 (14)
C3	0.0161 (16)	0.0196 (17)	0.0238 (17)	−0.0014 (13)	−0.0052 (13)	−0.0081 (14)
C4	0.0198 (17)	0.0187 (17)	0.0249 (18)	−0.0005 (13)	−0.0100 (14)	−0.0090 (14)
C5	0.0158 (15)	0.0145 (16)	0.0228 (17)	0.0026 (12)	−0.0095 (13)	−0.0059 (14)
C6	0.0143 (15)	0.0134 (15)	0.0170 (15)	−0.0017 (12)	−0.0037 (12)	−0.0054 (13)
C7	0.0130 (14)	0.0175 (16)	0.0174 (15)	0.0005 (12)	−0.0032 (12)	−0.0096 (13)
C8	0.0169 (16)	0.0200 (17)	0.0252 (18)	−0.0003 (13)	−0.0048 (13)	−0.0130 (15)
C9	0.0153 (16)	0.0163 (17)	0.0224 (17)	−0.0033 (13)	−0.0056 (13)	−0.0033 (14)
C10	0.0194 (16)	0.0217 (18)	0.0151 (15)	−0.0058 (13)	−0.0035 (13)	−0.0024 (14)
C11	0.0144 (15)	0.0200 (17)	0.0180 (16)	0.0010 (13)	−0.0060 (12)	−0.0085 (14)
C12	0.0252 (18)	0.0248 (19)	0.0189 (17)	−0.0015 (14)	−0.0050 (14)	−0.0106 (15)
C13	0.032 (2)	0.0183 (19)	0.031 (2)	−0.0063 (16)	−0.0062 (17)	−0.0036 (16)
C14	0.0276 (19)	0.027 (2)	0.0198 (17)	0.0009 (15)	−0.0077 (15)	−0.0115 (15)
C15	0.0143 (15)	0.0139 (16)	0.0228 (17)	0.0009 (12)	−0.0082 (13)	−0.0057 (13)
C16	0.0173 (16)	0.0187 (17)	0.0196 (16)	0.0004 (13)	−0.0058 (13)	−0.0080 (14)
C17	0.0159 (15)	0.0163 (16)	0.0197 (16)	0.0005 (12)	−0.0049 (13)	−0.0047 (14)
C18	0.0161 (16)	0.0161 (17)	0.0288 (18)	0.0019 (13)	−0.0105 (14)	−0.0082 (14)
C19	0.0205 (17)	0.0193 (17)	0.0263 (18)	0.0011 (13)	−0.0121 (14)	−0.0112 (15)
C20	0.0190 (16)	0.0145 (16)	0.0203 (16)	0.0010 (13)	−0.0074 (13)	−0.0063 (13)
C21	0.0249 (18)	0.031 (2)	0.0218 (18)	−0.0037 (15)	−0.0044 (14)	−0.0151 (16)
C22	0.0187 (17)	0.0194 (18)	0.032 (2)	−0.0020 (14)	−0.0091 (15)	−0.0090 (16)
C23	0.0207 (17)	0.0270 (19)	0.0235 (18)	−0.0049 (14)	−0.0049 (14)	−0.0124 (15)
C24	0.0218 (18)	0.030 (2)	0.0185 (17)	0.0027 (15)	−0.0073 (14)	−0.0087 (15)
C25	0.0160 (16)	0.0157 (17)	0.0249 (18)	−0.0036 (13)	−0.0043 (14)	−0.0032 (14)
C26	0.0222 (18)	0.026 (2)	0.0281 (19)	0.0005 (15)	−0.0122 (15)	−0.0087 (16)
C27	0.0249 (18)	0.0217 (18)	0.0186 (17)	0.0018 (14)	−0.0023 (14)	−0.0081 (15)
C28	0.039 (2)	0.035 (2)	0.0225 (19)	0.0111 (19)	−0.0091 (17)	−0.0056 (18)
C29	0.046 (3)	0.029 (2)	0.045 (3)	−0.0039 (19)	−0.009 (2)	−0.020 (2)

Geometric parameters (Å, º)

I1—I2	2.9235 (4)	C14—H14A	0.9800
I2—I3	2.9332 (5)	C14—H14B	0.9800
S1—C1	1.772 (3)	C14—H14C	0.9800
S1—C24	1.814 (4)	C15—C16	1.399 (5)
O1—C25	1.212 (4)	C15—C20	1.392 (5)
N1—C1	1.339 (4)	C16—C17	1.395 (5)
N1—C5	1.496 (4)	C16—C21	1.508 (5)
N1—C15	1.458 (4)	C17—H17	0.9500
N2—C1	1.329 (4)	C17—C18	1.397 (5)
N2—C2	1.486 (4)	C18—C19	1.395 (5)
N2—C6	1.448 (4)	C18—C22	1.510 (5)
C2—H2A	0.9900	C19—H19	0.9500
C2—H2B	0.9900	C19—C20	1.396 (5)
C2—C3	1.510 (5)	C20—C23	1.509 (5)
C3—H3A	0.9900	C21—H21A	0.9800
C3—H3B	0.9900	C21—H21B	0.9800
C3—C4	1.533 (5)	C21—H21C	0.9800
C4—H4A	0.9900	C22—H22A	0.9800
C4—H4B	0.9900	C22—H22B	0.9800
C4—C5	1.522 (5)	C22—H22C	0.9800
C5—H5A	0.9900	C23—H23A	0.9800
C5—H5B	0.9900	C23—H23B	0.9800
C6—C7	1.399 (4)	C23—H23C	0.9800
C6—C11	1.406 (4)	C24—H24A	0.9900
C7—C8	1.389 (5)	C24—H24B	0.9900
C7—C12	1.503 (5)	C24—C25	1.516 (5)
C8—H8	0.9500	C25—C26	1.503 (5)
C8—C9	1.398 (5)	C26—H26A	0.9900
C9—C10	1.386 (5)	C26—H26B	0.9900
C9—C13	1.502 (5)	C26—C27	1.537 (5)
C10—H10	0.9500	C27—H27	1.0000
C10—C11	1.385 (5)	C27—C28	1.520 (5)
C11—C14	1.514 (5)	C27—C29	1.521 (5)
C12—H12A	0.9800	C28—H28A	0.9800
C12—H12B	0.9800	C28—H28B	0.9800
C12—H12C	0.9800	C28—H28C	0.9800
C13—H13A	0.9800	C29—H29A	0.9800
C13—H13B	0.9800	C29—H29B	0.9800
C13—H13C	0.9800	C29—H29C	0.9800
I1—I2—I3	179.585 (12)	H14B—C14—H14C	109.5
C1—S1—C24	106.62 (16)	C16—C15—N1	119.3 (3)
C1—N1—C5	127.1 (3)	C20—C15—N1	117.9 (3)
C1—N1—C15	119.5 (3)	C20—C15—C16	122.7 (3)
C15—N1—C5	113.2 (3)	C15—C16—C21	121.5 (3)
C1—N2—C2	121.0 (3)	C17—C16—C15	117.5 (3)
C1—N2—C6	122.9 (3)	C17—C16—C21	121.0 (3)
C6—N2—C2	115.9 (3)	C16—C17—H17	119.1
N1—C1—S1	113.6 (2)	C16—C17—C18	121.8 (3)
N2—C1—S1	123.0 (3)	C18—C17—H17	119.1
N2—C1—N1	123.0 (3)	C17—C18—C22	121.1 (3)
N2—C2—H2A	109.1	C19—C18—C17	118.6 (3)
N2—C2—H2B	109.1	C19—C18—C22	120.3 (3)
N2—C2—C3	112.6 (3)	C18—C19—H19	119.1
H2A—C2—H2B	107.8	C18—C19—C20	121.7 (3)
C3—C2—H2A	109.1	C20—C19—H19	119.1
C3—C2—H2B	109.1	C15—C20—C19	117.7 (3)
C2—C3—H3A	109.3	C15—C20—C23	122.2 (3)
C2—C3—H3B	109.3	C19—C20—C23	120.0 (3)
C2—C3—C4	111.6 (3)	C16—C21—H21A	109.5
H3A—C3—H3B	108.0	C16—C21—H21B	109.5
C4—C3—H3A	109.3	C16—C21—H21C	109.5
C4—C3—H3B	109.3	H21A—C21—H21B	109.5
C3—C4—H4A	109.1	H21A—C21—H21C	109.5
C3—C4—H4B	109.1	H21B—C21—H21C	109.5
H4A—C4—H4B	107.9	C18—C22—H22A	109.5
C5—C4—C3	112.3 (3)	C18—C22—H22B	109.5
C5—C4—H4A	109.1	C18—C22—H22C	109.5
C5—C4—H4B	109.1	H22A—C22—H22B	109.5
N1—C5—C4	113.2 (3)	H22A—C22—H22C	109.5
N1—C5—H5A	108.9	H22B—C22—H22C	109.5
N1—C5—H5B	108.9	C20—C23—H23A	109.5
C4—C5—H5A	108.9	C20—C23—H23B	109.5
C4—C5—H5B	108.9	C20—C23—H23C	109.5
H5A—C5—H5B	107.7	H23A—C23—H23B	109.5
C7—C6—N2	120.5 (3)	H23A—C23—H23C	109.5
C7—C6—C11	121.6 (3)	H23B—C23—H23C	109.5
C11—C6—N2	117.8 (3)	S1—C24—H24A	110.5
C6—C7—C12	122.6 (3)	S1—C24—H24B	110.5
C8—C7—C6	117.6 (3)	H24A—C24—H24B	108.7
C8—C7—C12	119.8 (3)	C25—C24—S1	106.0 (2)
C7—C8—H8	118.8	C25—C24—H24A	110.5
C7—C8—C9	122.3 (3)	C25—C24—H24B	110.5
C9—C8—H8	118.8	O1—C25—C24	120.5 (3)
C8—C9—C13	120.8 (3)	O1—C25—C26	123.0 (3)
C10—C9—C8	118.0 (3)	C26—C25—C24	116.5 (3)
C10—C9—C13	121.2 (3)	C25—C26—H26A	108.7
C9—C10—H10	118.9	C25—C26—H26B	108.7
C11—C10—C9	122.3 (3)	C25—C26—C27	114.3 (3)
C11—C10—H10	118.9	H26A—C26—H26B	107.6
C6—C11—C14	122.1 (3)	C27—C26—H26A	108.7
C10—C11—C6	118.1 (3)	C27—C26—H26B	108.7
C10—C11—C14	119.8 (3)	C26—C27—H27	108.3
C7—C12—H12A	109.5	C28—C27—C26	108.9 (3)
C7—C12—H12B	109.5	C28—C27—H27	108.3
C7—C12—H12C	109.5	C28—C27—C29	111.2 (3)
H12A—C12—H12B	109.5	C29—C27—C26	111.8 (3)
H12A—C12—H12C	109.5	C29—C27—H27	108.3
H12B—C12—H12C	109.5	C27—C28—H28A	109.5
C9—C13—H13A	109.5	C27—C28—H28B	109.5
C9—C13—H13B	109.5	C27—C28—H28C	109.5
C9—C13—H13C	109.5	H28A—C28—H28B	109.5
H13A—C13—H13B	109.5	H28A—C28—H28C	109.5
H13A—C13—H13C	109.5	H28B—C28—H28C	109.5
H13B—C13—H13C	109.5	C27—C29—H29A	109.5
C11—C14—H14A	109.5	C27—C29—H29B	109.5
C11—C14—H14B	109.5	C27—C29—H29C	109.5
C11—C14—H14C	109.5	H29A—C29—H29B	109.5
H14A—C14—H14B	109.5	H29A—C29—H29C	109.5
H14A—C14—H14C	109.5	H29B—C29—H29C	109.5
S1—C24—C25—O1	6.3 (4)	C6—C7—C8—C9	0.1 (5)
S1—C24—C25—C26	−173.5 (3)	C7—C6—C11—C10	−3.3 (5)
O1—C25—C26—C27	119.7 (4)	C7—C6—C11—C14	177.4 (3)
N1—C15—C16—C17	−177.1 (3)	C7—C8—C9—C10	−2.5 (5)
N1—C15—C16—C21	3.4 (5)	C7—C8—C9—C13	176.6 (3)
N1—C15—C20—C19	177.0 (3)	C8—C9—C10—C11	2.1 (5)
N1—C15—C20—C23	−1.3 (5)	C9—C10—C11—C6	0.7 (5)
N2—C2—C3—C4	52.3 (4)	C9—C10—C11—C14	−180.0 (3)
N2—C6—C7—C8	−179.6 (3)	C11—C6—C7—C8	2.9 (5)
N2—C6—C7—C12	0.6 (5)	C11—C6—C7—C12	−176.9 (3)
N2—C6—C11—C10	179.1 (3)	C12—C7—C8—C9	179.9 (3)
N2—C6—C11—C14	−0.1 (5)	C13—C9—C10—C11	−177.0 (3)
C1—S1—C24—C25	−177.9 (2)	C15—N1—C1—S1	34.1 (4)
C1—N1—C5—C4	28.3 (5)	C15—N1—C1—N2	−152.8 (3)
C1—N1—C15—C16	−106.6 (4)	C15—N1—C5—C4	−157.3 (3)
C1—N1—C15—C20	77.8 (4)	C15—C16—C17—C18	0.6 (5)
C1—N2—C2—C3	−79.9 (4)	C16—C15—C20—C19	1.6 (5)
C1—N2—C6—C7	75.7 (4)	C16—C15—C20—C23	−176.7 (3)
C1—N2—C6—C11	−106.7 (4)	C16—C17—C18—C19	0.7 (5)
C2—N2—C1—S1	−174.2 (2)	C16—C17—C18—C22	179.1 (3)
C2—N2—C1—N1	13.4 (5)	C17—C18—C19—C20	−0.9 (5)
C2—N2—C6—C7	−108.4 (3)	C18—C19—C20—C15	−0.2 (5)
C2—N2—C6—C11	69.2 (4)	C18—C19—C20—C23	178.2 (3)
C2—C3—C4—C5	33.1 (4)	C20—C15—C16—C17	−1.8 (5)
C3—C4—C5—N1	−78.5 (4)	C20—C15—C16—C21	178.7 (3)
C5—N1—C1—S1	−151.9 (3)	C21—C16—C17—C18	−179.9 (3)
C5—N1—C1—N2	21.2 (5)	C22—C18—C19—C20	−179.3 (3)
C5—N1—C15—C16	78.5 (4)	C24—S1—C1—N1	−131.5 (3)
C5—N1—C15—C20	−97.0 (4)	C24—S1—C1—N2	55.4 (3)
C6—N2—C1—S1	1.5 (4)	C24—C25—C26—C27	−60.5 (4)
C6—N2—C1—N1	−171.0 (3)	C25—C26—C27—C28	−178.6 (3)
C6—N2—C2—C3	104.1 (3)	C25—C26—C27—C29	−55.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···I1	0.99	3.07	3.693 (3)	122
C2—H2B···I2	0.99	3.17	3.986 (3)	141

(SDiazMesSeMIBK_I3)

Crystal data

I3·C29H41N2OSe	Z = 2
Mr = 893.30	F(000) = 860
Triclinic, P1	Dx = 1.809 Mg m^−3
a = 8.8091 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.2584 (8) Å	Cell parameters from 9322 reflections
c = 15.1228 (9) Å	θ = 2.4–29.6°
α = 63.952 (2)°	µ = 3.99 mm^−1
β = 74.061 (2)°	T = 100 K
γ = 81.113 (2)°	Block, red
V = 1639.67 (17) Å^3	0.17 × 0.11 × 0.08 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	7989 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.041
φ and ω scans	θmax = 29.6°, θmin = 2.4°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −12→12
Tmin = 0.640, Tmax = 0.746	k = −19→19
75078 measured reflections	l = −21→21
9229 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.052	H-atom parameters constrained
S = 1.14	w = 1/[σ^2(Fo^2) + (0.0083P)^2 + 2.5037P] where P = (Fo^2 + 2Fc^2)/3
9229 reflections	(Δ/σ)max = 0.001
333 parameters	Δρmax = 1.18 e Å^−3
0 restraints	Δρmin = −1.66 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.56024 (2)	−0.00543 (2)	0.26292 (2)	0.03391 (5)
I2	0.72482 (2)	0.19059 (2)	0.17544 (2)	0.01934 (4)
I3	0.89122 (2)	0.38487 (2)	0.08800 (2)	0.02363 (4)
Se1	0.04429 (2)	0.46632 (2)	0.36803 (2)	0.01641 (5)
O1	−0.2198 (2)	0.59460 (14)	0.33074 (14)	0.0274 (4)
N1	0.2595 (2)	0.29977 (14)	0.40427 (14)	0.0139 (3)
N2	0.3824 (2)	0.45914 (14)	0.29884 (14)	0.0135 (3)
C1	0.2541 (2)	0.40347 (16)	0.35019 (16)	0.0134 (4)
C2	0.5407 (2)	0.40814 (17)	0.27903 (17)	0.0169 (4)
H2A	0.611534	0.460062	0.220870	0.020*
H2B	0.530612	0.351443	0.260254	0.020*
C3	0.6152 (3)	0.36290 (18)	0.36972 (18)	0.0181 (4)
H3A	0.644487	0.420606	0.380685	0.022*
H3B	0.712884	0.321943	0.355665	0.022*
C4	0.5016 (3)	0.29243 (18)	0.46569 (18)	0.0178 (4)
H4A	0.563658	0.241270	0.513273	0.021*
H4B	0.434425	0.335673	0.498970	0.021*
C5	0.3967 (3)	0.23407 (17)	0.44382 (18)	0.0166 (4)
H5A	0.461021	0.208212	0.393546	0.020*
H5B	0.356023	0.172588	0.506783	0.020*
C6	0.3759 (2)	0.57255 (16)	0.25038 (16)	0.0129 (4)
C7	0.3547 (2)	0.62997 (17)	0.30804 (16)	0.0143 (4)
C8	0.3491 (3)	0.73870 (17)	0.25717 (18)	0.0168 (4)
H8	0.335672	0.779250	0.294784	0.020*
C9	0.3627 (3)	0.78963 (17)	0.15321 (18)	0.0183 (4)
C10	0.3889 (3)	0.72988 (18)	0.09825 (17)	0.0181 (4)
H10	0.401198	0.764083	0.026951	0.022*
C11	0.3978 (3)	0.62098 (17)	0.14482 (16)	0.0159 (4)
C12	0.3429 (3)	0.57902 (18)	0.42043 (17)	0.0184 (4)
H12A	0.448886	0.557814	0.433104	0.028*
H12B	0.278394	0.517385	0.451622	0.028*
H12C	0.293679	0.628703	0.449676	0.028*
C13	0.3481 (3)	0.90691 (19)	0.1020 (2)	0.0280 (5)
H13A	0.246885	0.931139	0.133795	0.042*
H13B	0.353046	0.928993	0.030135	0.042*
H13C	0.434792	0.936981	0.108788	0.042*
C14	0.4265 (3)	0.55979 (19)	0.08152 (18)	0.0226 (5)
H14A	0.396947	0.603560	0.017142	0.034*
H14B	0.362586	0.497658	0.117916	0.034*
H14C	0.538605	0.538399	0.068364	0.034*
C15	0.1277 (2)	0.23841 (16)	0.42230 (17)	0.0151 (4)
C16	0.1151 (3)	0.21633 (17)	0.34324 (17)	0.0162 (4)
C17	−0.0074 (3)	0.15420 (18)	0.36231 (18)	0.0186 (4)
H17	−0.018867	0.138494	0.309645	0.022*
C18	−0.1138 (3)	0.11430 (17)	0.45592 (18)	0.0182 (4)
C19	−0.0950 (3)	0.13699 (17)	0.53315 (18)	0.0182 (4)
H19	−0.166541	0.109587	0.597502	0.022*
C20	0.0256 (3)	0.19860 (17)	0.51859 (17)	0.0162 (4)
C21	0.2293 (3)	0.2570 (2)	0.24127 (18)	0.0226 (5)
H21A	0.215237	0.333100	0.207742	0.034*
H21B	0.209252	0.225586	0.199650	0.034*
H21C	0.337744	0.238655	0.250064	0.034*
C22	−0.2434 (3)	0.04532 (18)	0.4740 (2)	0.0220 (5)
H22A	−0.210789	−0.028130	0.508358	0.033*
H22B	−0.263391	0.057748	0.409059	0.033*
H22C	−0.340088	0.061644	0.516426	0.033*
C23	0.0446 (3)	0.2211 (2)	0.60342 (18)	0.0228 (5)
H23A	−0.047313	0.196810	0.660492	0.034*
H23B	0.052815	0.296490	0.579708	0.034*
H23C	0.140551	0.184659	0.625213	0.034*
C24	0.0241 (3)	0.5622 (2)	0.23151 (19)	0.0282 (6)
H24A	0.103682	0.616617	0.199786	0.034*
H24B	0.037624	0.524216	0.188418	0.034*
C25	−0.1416 (3)	0.61029 (18)	0.24598 (19)	0.0205 (5)
C26	−0.1997 (3)	0.6772 (2)	0.1516 (2)	0.0254 (5)
H26A	−0.307891	0.704526	0.171166	0.030*
H26B	−0.205961	0.632844	0.117531	0.030*
C27	−0.0959 (3)	0.76942 (19)	0.07604 (18)	0.0226 (5)
H27	0.010448	0.741090	0.051836	0.027*
C28	−0.1698 (4)	0.8312 (2)	−0.0148 (2)	0.0353 (7)
H28A	−0.183514	0.784491	−0.043719	0.053*
H28B	−0.100331	0.887286	−0.066010	0.053*
H28C	−0.272847	0.861528	0.007179	0.053*
C29	−0.0746 (4)	0.8387 (2)	0.1248 (3)	0.0398 (7)
H29A	−0.177981	0.866557	0.149714	0.060*
H29B	−0.007656	0.896625	0.074556	0.060*
H29C	−0.024420	0.797418	0.181449	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.03473 (10)	0.03072 (10)	0.03661 (10)	−0.00860 (7)	−0.00581 (8)	−0.01347 (8)
I2	0.01775 (7)	0.02374 (8)	0.01652 (7)	0.00061 (5)	−0.00455 (5)	−0.00852 (6)
I3	0.01934 (7)	0.02508 (8)	0.02477 (8)	−0.00127 (6)	−0.00152 (6)	−0.01089 (7)
Se1	0.01227 (9)	0.01410 (10)	0.01832 (11)	0.00093 (7)	−0.00392 (8)	−0.00298 (8)
O1	0.0189 (8)	0.0255 (9)	0.0243 (9)	0.0011 (7)	−0.0009 (7)	−0.0013 (7)
N1	0.0127 (8)	0.0116 (8)	0.0175 (9)	0.0005 (6)	−0.0067 (7)	−0.0047 (7)
N2	0.0129 (8)	0.0132 (8)	0.0141 (8)	0.0005 (6)	−0.0045 (7)	−0.0050 (7)
C1	0.0137 (9)	0.0131 (9)	0.0150 (10)	0.0015 (7)	−0.0065 (8)	−0.0062 (8)
C2	0.0132 (9)	0.0156 (10)	0.0204 (11)	0.0015 (8)	−0.0020 (8)	−0.0080 (9)
C3	0.0150 (10)	0.0159 (10)	0.0229 (11)	0.0006 (8)	−0.0072 (9)	−0.0065 (9)
C4	0.0176 (10)	0.0163 (10)	0.0215 (11)	−0.0001 (8)	−0.0102 (9)	−0.0066 (9)
C5	0.0156 (10)	0.0119 (10)	0.0219 (11)	0.0015 (8)	−0.0093 (8)	−0.0043 (8)
C6	0.0112 (9)	0.0113 (9)	0.0151 (10)	−0.0010 (7)	−0.0033 (7)	−0.0043 (8)
C7	0.0110 (9)	0.0151 (10)	0.0166 (10)	−0.0005 (7)	−0.0036 (8)	−0.0062 (8)
C8	0.0149 (10)	0.0146 (10)	0.0221 (11)	0.0002 (8)	−0.0051 (8)	−0.0085 (9)
C9	0.0162 (10)	0.0138 (10)	0.0217 (11)	−0.0016 (8)	−0.0052 (9)	−0.0037 (9)
C10	0.0168 (10)	0.0184 (11)	0.0149 (10)	−0.0023 (8)	−0.0048 (8)	−0.0022 (9)
C11	0.0147 (10)	0.0187 (10)	0.0135 (10)	0.0002 (8)	−0.0044 (8)	−0.0056 (8)
C12	0.0223 (11)	0.0191 (11)	0.0152 (10)	−0.0011 (9)	−0.0056 (8)	−0.0075 (9)
C13	0.0322 (13)	0.0155 (11)	0.0295 (13)	−0.0036 (10)	−0.0079 (11)	−0.0021 (10)
C14	0.0303 (12)	0.0224 (12)	0.0168 (11)	0.0013 (10)	−0.0083 (10)	−0.0088 (9)
C15	0.0146 (9)	0.0109 (9)	0.0212 (11)	0.0003 (7)	−0.0081 (8)	−0.0060 (8)
C16	0.0150 (10)	0.0148 (10)	0.0184 (10)	0.0009 (8)	−0.0064 (8)	−0.0056 (8)
C17	0.0190 (10)	0.0180 (11)	0.0235 (11)	0.0011 (8)	−0.0105 (9)	−0.0101 (9)
C18	0.0163 (10)	0.0124 (10)	0.0259 (12)	0.0012 (8)	−0.0110 (9)	−0.0049 (9)
C19	0.0154 (10)	0.0145 (10)	0.0209 (11)	−0.0009 (8)	−0.0042 (8)	−0.0039 (9)
C20	0.0171 (10)	0.0129 (10)	0.0194 (11)	0.0021 (8)	−0.0079 (8)	−0.0061 (8)
C21	0.0225 (11)	0.0290 (13)	0.0187 (11)	−0.0047 (9)	−0.0042 (9)	−0.0113 (10)
C22	0.0176 (10)	0.0176 (11)	0.0311 (13)	−0.0030 (8)	−0.0098 (10)	−0.0072 (10)
C23	0.0234 (11)	0.0260 (12)	0.0214 (12)	−0.0052 (9)	−0.0046 (9)	−0.0111 (10)
C24	0.0201 (11)	0.0400 (15)	0.0175 (11)	0.0078 (10)	−0.0069 (9)	−0.0073 (11)
C25	0.0151 (10)	0.0165 (11)	0.0241 (12)	−0.0020 (8)	−0.0060 (9)	−0.0020 (9)
C26	0.0184 (11)	0.0269 (13)	0.0269 (13)	0.0019 (9)	−0.0116 (10)	−0.0049 (10)
C27	0.0223 (11)	0.0213 (12)	0.0187 (11)	0.0035 (9)	−0.0032 (9)	−0.0059 (9)
C28	0.0377 (15)	0.0317 (15)	0.0253 (13)	0.0128 (12)	−0.0098 (12)	−0.0049 (12)
C29	0.0489 (18)	0.0298 (15)	0.0427 (18)	−0.0024 (13)	−0.0096 (15)	−0.0172 (14)

Geometric parameters (Å, º)

I1—I2	2.9351 (3)	C14—H14A	0.9800
I2—I3	2.9230 (3)	C14—H14B	0.9800
Se1—C1	1.928 (2)	C14—H14C	0.9800
Se1—C24	1.952 (2)	C15—C16	1.398 (3)
O1—C25	1.216 (3)	C15—C20	1.401 (3)
N1—C1	1.340 (3)	C16—C17	1.390 (3)
N1—C5	1.500 (3)	C16—C21	1.506 (3)
N1—C15	1.456 (3)	C17—H17	0.9500
N2—C1	1.328 (3)	C17—C18	1.391 (3)
N2—C2	1.487 (3)	C18—C19	1.397 (3)
N2—C6	1.452 (3)	C18—C22	1.512 (3)
C2—H2A	0.9900	C19—H19	0.9500
C2—H2B	0.9900	C19—C20	1.392 (3)
C2—C3	1.521 (3)	C20—C23	1.508 (3)
C3—H3A	0.9900	C21—H21A	0.9800
C3—H3B	0.9900	C21—H21B	0.9800
C3—C4	1.533 (3)	C21—H21C	0.9800
C4—H4A	0.9900	C22—H22A	0.9800
C4—H4B	0.9900	C22—H22B	0.9800
C4—C5	1.518 (3)	C22—H22C	0.9800
C5—H5A	0.9900	C23—H23A	0.9800
C5—H5B	0.9900	C23—H23B	0.9800
C6—C7	1.399 (3)	C23—H23C	0.9800
C6—C11	1.402 (3)	C24—H24A	0.9900
C7—C8	1.395 (3)	C24—H24B	0.9900
C7—C12	1.506 (3)	C24—C25	1.515 (3)
C8—H8	0.9500	C25—C26	1.504 (3)
C8—C9	1.391 (3)	C26—H26A	0.9900
C9—C10	1.388 (3)	C26—H26B	0.9900
C9—C13	1.505 (3)	C26—C27	1.533 (4)
C10—H10	0.9500	C27—H27	1.0000
C10—C11	1.395 (3)	C27—C28	1.529 (4)
C11—C14	1.508 (3)	C27—C29	1.526 (4)
C12—H12A	0.9800	C28—H28A	0.9800
C12—H12B	0.9800	C28—H28B	0.9800
C12—H12C	0.9800	C28—H28C	0.9800
C13—H13A	0.9800	C29—H29A	0.9800
C13—H13B	0.9800	C29—H29B	0.9800
C13—H13C	0.9800	C29—H29C	0.9800
I3—I2—I1	179.522 (8)	H14B—C14—H14C	109.5
C1—Se1—C24	104.88 (10)	C16—C15—N1	117.64 (19)
C1—N1—C5	126.80 (18)	C16—C15—C20	122.8 (2)
C1—N1—C15	119.86 (17)	C20—C15—N1	119.43 (19)
C15—N1—C5	113.14 (16)	C15—C16—C21	122.0 (2)
C1—N2—C2	121.40 (18)	C17—C16—C15	117.3 (2)
C1—N2—C6	122.66 (17)	C17—C16—C21	120.7 (2)
C6—N2—C2	115.68 (17)	C16—C17—H17	118.9
N1—C1—Se1	113.47 (15)	C16—C17—C18	122.2 (2)
N2—C1—Se1	122.89 (15)	C18—C17—H17	118.9
N2—C1—N1	123.18 (19)	C17—C18—C19	118.5 (2)
N2—C2—H2A	109.0	C17—C18—C22	120.5 (2)
N2—C2—H2B	109.0	C19—C18—C22	121.0 (2)
N2—C2—C3	112.86 (18)	C18—C19—H19	119.0
H2A—C2—H2B	107.8	C20—C19—C18	121.9 (2)
C3—C2—H2A	109.0	C20—C19—H19	119.0
C3—C2—H2B	109.0	C15—C20—C23	121.7 (2)
C2—C3—H3A	109.4	C19—C20—C15	117.3 (2)
C2—C3—H3B	109.4	C19—C20—C23	121.0 (2)
C2—C3—C4	111.36 (18)	C16—C21—H21A	109.5
H3A—C3—H3B	108.0	C16—C21—H21B	109.5
C4—C3—H3A	109.4	C16—C21—H21C	109.5
C4—C3—H3B	109.4	H21A—C21—H21B	109.5
C3—C4—H4A	109.1	H21A—C21—H21C	109.5
C3—C4—H4B	109.1	H21B—C21—H21C	109.5
H4A—C4—H4B	107.8	C18—C22—H22A	109.5
C5—C4—C3	112.51 (19)	C18—C22—H22B	109.5
C5—C4—H4A	109.1	C18—C22—H22C	109.5
C5—C4—H4B	109.1	H22A—C22—H22B	109.5
N1—C5—C4	113.31 (17)	H22A—C22—H22C	109.5
N1—C5—H5A	108.9	H22B—C22—H22C	109.5
N1—C5—H5B	108.9	C20—C23—H23A	109.5
C4—C5—H5A	108.9	C20—C23—H23B	109.5
C4—C5—H5B	108.9	C20—C23—H23C	109.5
H5A—C5—H5B	107.7	H23A—C23—H23B	109.5
C7—C6—N2	120.19 (19)	H23A—C23—H23C	109.5
C7—C6—C11	122.0 (2)	H23B—C23—H23C	109.5
C11—C6—N2	117.75 (19)	Se1—C24—H24A	110.8
C6—C7—C12	122.61 (19)	Se1—C24—H24B	110.8
C8—C7—C6	117.5 (2)	H24A—C24—H24B	108.9
C8—C7—C12	119.9 (2)	C25—C24—Se1	104.59 (16)
C7—C8—H8	118.9	C25—C24—H24A	110.8
C9—C8—C7	122.1 (2)	C25—C24—H24B	110.8
C9—C8—H8	118.9	O1—C25—C24	119.9 (2)
C8—C9—C13	120.5 (2)	O1—C25—C26	123.4 (2)
C10—C9—C8	118.5 (2)	C26—C25—C24	116.6 (2)
C10—C9—C13	121.0 (2)	C25—C26—H26A	108.7
C9—C10—H10	119.1	C25—C26—H26B	108.7
C9—C10—C11	121.8 (2)	C25—C26—C27	114.3 (2)
C11—C10—H10	119.1	H26A—C26—H26B	107.6
C6—C11—C14	122.5 (2)	C27—C26—H26A	108.7
C10—C11—C6	117.9 (2)	C27—C26—H26B	108.7
C10—C11—C14	119.6 (2)	C26—C27—H27	108.3
C7—C12—H12A	109.5	C28—C27—C26	108.7 (2)
C7—C12—H12B	109.5	C28—C27—H27	108.3
C7—C12—H12C	109.5	C29—C27—C26	111.7 (2)
H12A—C12—H12B	109.5	C29—C27—H27	108.3
H12A—C12—H12C	109.5	C29—C27—C28	111.4 (2)
H12B—C12—H12C	109.5	C27—C28—H28A	109.5
C9—C13—H13A	109.5	C27—C28—H28B	109.5
C9—C13—H13B	109.5	C27—C28—H28C	109.5
C9—C13—H13C	109.5	H28A—C28—H28B	109.5
H13A—C13—H13B	109.5	H28A—C28—H28C	109.5
H13A—C13—H13C	109.5	H28B—C28—H28C	109.5
H13B—C13—H13C	109.5	C27—C29—H29A	109.5
C11—C14—H14A	109.5	C27—C29—H29B	109.5
C11—C14—H14B	109.5	C27—C29—H29C	109.5
C11—C14—H14C	109.5	H29A—C29—H29B	109.5
H14A—C14—H14B	109.5	H29A—C29—H29C	109.5
H14A—C14—H14C	109.5	H29B—C29—H29C	109.5
Se1—C24—C25—O1	8.9 (3)	C6—C7—C8—C9	0.5 (3)
Se1—C24—C25—C26	−171.74 (18)	C7—C6—C11—C10	−3.6 (3)
O1—C25—C26—C27	121.8 (3)	C7—C6—C11—C14	177.8 (2)
N1—C15—C16—C17	177.50 (19)	C7—C8—C9—C10	−2.6 (3)
N1—C15—C16—C21	−2.1 (3)	C7—C8—C9—C13	176.9 (2)
N1—C15—C20—C19	−177.53 (19)	C8—C9—C10—C11	1.7 (3)
N1—C15—C20—C23	2.5 (3)	C9—C10—C11—C6	1.3 (3)
N2—C2—C3—C4	51.5 (2)	C9—C10—C11—C14	−180.0 (2)
N2—C6—C7—C8	−179.91 (18)	C11—C6—C7—C8	2.7 (3)
N2—C6—C7—C12	2.0 (3)	C11—C6—C7—C12	−175.4 (2)
N2—C6—C11—C10	178.95 (18)	C12—C7—C8—C9	178.7 (2)
N2—C6—C11—C14	0.3 (3)	C13—C9—C10—C11	−177.9 (2)
C1—N1—C5—C4	29.1 (3)	C15—N1—C1—Se1	33.5 (2)
C1—N1—C15—C16	77.8 (3)	C15—N1—C1—N2	−154.0 (2)
C1—N1—C15—C20	−106.3 (2)	C15—N1—C5—C4	−156.09 (19)
C1—N2—C2—C3	−79.4 (2)	C15—C16—C17—C18	−0.4 (3)
C1—N2—C6—C7	77.7 (3)	C16—C15—C20—C19	−1.8 (3)
C1—N2—C6—C11	−104.7 (2)	C16—C15—C20—C23	178.2 (2)
C2—N2—C1—Se1	−174.64 (15)	C16—C17—C18—C19	−0.6 (3)
C2—N2—C1—N1	13.6 (3)	C16—C17—C18—C22	−178.8 (2)
C2—N2—C6—C7	−108.1 (2)	C17—C18—C19—C20	0.5 (3)
C2—N2—C6—C11	69.4 (2)	C18—C19—C20—C15	0.6 (3)
C2—C3—C4—C5	33.7 (3)	C18—C19—C20—C23	−179.4 (2)
C3—C4—C5—N1	−79.3 (2)	C20—C15—C16—C17	1.7 (3)
C5—N1—C1—Se1	−152.00 (17)	C20—C15—C16—C21	−177.9 (2)
C5—N1—C1—N2	20.5 (3)	C21—C16—C17—C18	179.2 (2)
C5—N1—C15—C16	−97.4 (2)	C22—C18—C19—C20	178.7 (2)
C5—N1—C15—C20	78.6 (2)	C24—C25—C26—C27	−57.6 (3)
C6—N2—C1—Se1	−0.8 (3)	C25—C26—C27—C28	−179.1 (2)
C6—N2—C1—N1	−172.55 (19)	C25—C26—C27—C29	−55.8 (3)
C6—N2—C2—C3	106.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···I3	0.99	3.10	3.690 (2)	120
C2—H2B···I2	0.99	3.16	4.003 (2)	144
C3—H3A···O1^i	0.99	2.63	3.560 (3)	156

Symmetry code: (i) x+1, y, z.

(SDiazMesS_12F4DIB)

Crystal data

C6F4I2·C23H30N2S	Dx = 1.765 Mg m^−3
Mr = 768.41	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 9353 reflections
a = 7.6668 (5) Å	θ = 2.9–28.4°
b = 16.8546 (11) Å	µ = 2.30 mm^−1
c = 22.3786 (15) Å	T = 100 K
V = 2891.8 (3) Å^3	Needle, colourless
Z = 4	0.22 × 0.07 × 0.07 mm
F(000) = 1504

Data collection

Bruker D8 Venture Photon 2 diffractometer	6786 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.044
φ and ω scans	θmax = 28.4°, θmin = 2.9°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −10→10
Tmin = 0.621, Tmax = 0.746	k = −22→22
50096 measured reflections	l = −29→29
7186 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.025	H-atom parameters constrained
wR(F^2) = 0.058	w = 1/[σ^2(Fo^2) + (0.0178P)^2 + 2.9992P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.002
7186 reflections	Δρmax = 0.77 e Å^−3
349 parameters	Δρmin = −0.70 e Å^−3
1 restraint	Absolute structure: Flack x determined using 3124 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Primary atom site location: dual	Absolute structure parameter: −0.025 (7)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.76980 (3)	0.62670 (2)	0.46051 (2)	0.02765 (7)
I2	0.97868 (5)	0.51579 (2)	0.33758 (2)	0.04162 (10)
S1	0.60961 (14)	0.55911 (7)	0.58283 (5)	0.0232 (2)
F1	1.1171 (5)	0.6411 (2)	0.24692 (15)	0.0512 (9)
F2	1.1071 (5)	0.8009 (2)	0.24353 (15)	0.0501 (9)
F3	0.9486 (4)	0.88308 (16)	0.33257 (17)	0.0420 (8)
F4	0.8078 (4)	0.80691 (16)	0.42584 (13)	0.0328 (6)
N1	0.3091 (5)	0.5365 (2)	0.63715 (19)	0.0265 (8)
N2	0.3786 (5)	0.4428 (2)	0.5645 (2)	0.0305 (9)
C1	0.4198 (6)	0.5102 (2)	0.5951 (2)	0.0200 (9)
C2	0.1806 (8)	0.4819 (4)	0.6655 (3)	0.0432 (14)
H2A	0.229976	0.427654	0.667154	0.052*
H2B	0.157212	0.499472	0.706911	0.052*
C3	0.0158 (8)	0.4806 (4)	0.6313 (3)	0.0493 (16)
H3A	−0.046060	0.531689	0.636781	0.059*
H3B	−0.060145	0.437740	0.646715	0.059*
C4	0.0508 (7)	0.4673 (4)	0.5657 (3)	0.0431 (14)
H4A	0.080531	0.518610	0.546703	0.052*
H4B	−0.056322	0.446880	0.546392	0.052*
C5	0.2001 (8)	0.4085 (4)	0.5554 (3)	0.0487 (15)
H5A	0.185025	0.362981	0.582901	0.058*
H5B	0.191928	0.387880	0.514045	0.058*
C6	0.3364 (6)	0.6117 (3)	0.6666 (2)	0.0232 (9)
C7	0.4201 (6)	0.6116 (3)	0.7220 (2)	0.0224 (9)
C8	0.4381 (6)	0.6831 (3)	0.7517 (2)	0.0237 (9)
H8	0.492427	0.683636	0.789888	0.028*
C9	0.3790 (5)	0.7543 (3)	0.72750 (19)	0.0215 (8)
C10	0.2966 (6)	0.7529 (3)	0.6722 (2)	0.0233 (9)
H10	0.255033	0.800920	0.655168	0.028*
C11	0.2742 (6)	0.6814 (3)	0.6412 (2)	0.0240 (9)
C12	0.4979 (7)	0.5365 (3)	0.7482 (2)	0.0328 (11)
H12A	0.566656	0.549750	0.783683	0.049*
H12B	0.573296	0.511151	0.718387	0.049*
H12C	0.403853	0.499932	0.759285	0.049*
C13	0.4087 (7)	0.8325 (3)	0.7592 (2)	0.0290 (10)
H13A	0.355962	0.830439	0.799039	0.043*
H13B	0.355066	0.875461	0.736079	0.043*
H13C	0.534227	0.842229	0.762911	0.043*
C14	0.1852 (7)	0.6816 (3)	0.5808 (2)	0.0359 (11)
H14A	0.265106	0.660354	0.550567	0.054*
H14B	0.152644	0.736009	0.570130	0.054*
H14C	0.080179	0.648495	0.582509	0.054*
C15	0.5100 (6)	0.4061 (3)	0.5274 (2)	0.0246 (9)
C16	0.5122 (6)	0.4250 (3)	0.4669 (2)	0.0298 (10)
C17	0.6364 (8)	0.3875 (3)	0.4312 (2)	0.0357 (12)
H17	0.641079	0.400304	0.389903	0.043*
C18	0.7511 (7)	0.3334 (3)	0.4533 (3)	0.0339 (12)
C19	0.7444 (7)	0.3146 (3)	0.5140 (3)	0.0327 (11)
H19	0.823037	0.276326	0.529601	0.039*
C20	0.6242 (7)	0.3511 (3)	0.5523 (2)	0.0262 (10)
C21	0.3875 (9)	0.4837 (3)	0.4399 (3)	0.0436 (14)
H21A	0.269598	0.461286	0.439790	0.065*
H21B	0.423136	0.495468	0.398751	0.065*
H21C	0.388556	0.532697	0.463461	0.065*
C22	0.8837 (10)	0.2938 (4)	0.4130 (3)	0.0569 (18)
H22A	0.848212	0.300223	0.371173	0.085*
H22B	0.890619	0.237185	0.422639	0.085*
H22C	0.998228	0.318399	0.418976	0.085*
C23	0.6163 (8)	0.3323 (3)	0.6176 (2)	0.0380 (12)
H23A	0.716140	0.298929	0.628511	0.057*
H23B	0.507779	0.303869	0.626396	0.057*
H23C	0.620007	0.381638	0.640710	0.057*
C24	0.8881 (6)	0.6816 (3)	0.3862 (2)	0.0245 (9)
C25	0.9652 (6)	0.6393 (3)	0.3394 (3)	0.0286 (9)
C26	1.0380 (7)	0.6802 (4)	0.2921 (2)	0.0347 (12)
C27	1.0339 (7)	0.7622 (4)	0.2899 (2)	0.0349 (12)
C28	0.9552 (6)	0.8040 (3)	0.3352 (3)	0.0304 (10)
C29	0.8843 (6)	0.7634 (3)	0.3828 (2)	0.0263 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02956 (14)	0.02609 (13)	0.02730 (13)	−0.00367 (11)	−0.00535 (16)	0.00388 (13)
I2	0.0456 (2)	0.03001 (16)	0.0492 (2)	0.00803 (14)	−0.01249 (18)	−0.01082 (18)
S1	0.0195 (5)	0.0228 (5)	0.0272 (5)	−0.0043 (4)	0.0023 (4)	−0.0038 (4)
F1	0.055 (2)	0.066 (2)	0.0320 (17)	0.0002 (18)	0.0085 (15)	−0.0162 (17)
F2	0.053 (2)	0.070 (2)	0.0273 (16)	−0.0194 (19)	0.0003 (15)	0.0126 (16)
F3	0.0516 (19)	0.0291 (14)	0.0452 (19)	−0.0074 (13)	−0.0098 (16)	0.0117 (15)
F4	0.0375 (16)	0.0265 (14)	0.0343 (16)	−0.0003 (12)	0.0019 (13)	−0.0042 (12)
N1	0.0236 (19)	0.0231 (19)	0.033 (2)	−0.0070 (15)	0.0090 (16)	−0.0065 (16)
N2	0.0211 (19)	0.029 (2)	0.042 (2)	−0.0035 (16)	0.0062 (17)	−0.0102 (18)
C1	0.018 (2)	0.0169 (19)	0.025 (2)	0.0008 (15)	−0.0025 (16)	0.0050 (16)
C2	0.040 (3)	0.042 (3)	0.048 (3)	−0.009 (3)	0.009 (3)	0.000 (3)
C3	0.033 (3)	0.049 (4)	0.065 (4)	0.001 (3)	0.006 (3)	−0.001 (3)
C4	0.028 (3)	0.037 (3)	0.065 (4)	0.000 (2)	−0.008 (3)	−0.006 (3)
C5	0.036 (3)	0.041 (3)	0.070 (4)	−0.008 (3)	−0.002 (3)	−0.013 (3)
C6	0.023 (2)	0.022 (2)	0.025 (2)	−0.0039 (17)	0.0050 (17)	−0.0035 (17)
C7	0.025 (2)	0.021 (2)	0.021 (2)	0.0015 (17)	0.0059 (17)	0.0036 (16)
C8	0.025 (2)	0.029 (2)	0.018 (2)	0.0015 (18)	−0.0009 (16)	0.0001 (17)
C9	0.019 (2)	0.024 (2)	0.021 (2)	0.0004 (16)	0.0032 (16)	−0.0038 (17)
C10	0.022 (2)	0.025 (2)	0.023 (2)	0.0053 (17)	0.0049 (17)	0.0019 (18)
C11	0.020 (2)	0.031 (2)	0.021 (2)	0.0016 (18)	−0.0005 (17)	−0.0008 (18)
C12	0.039 (3)	0.025 (2)	0.035 (3)	0.005 (2)	0.003 (2)	0.010 (2)
C13	0.030 (2)	0.024 (2)	0.034 (3)	0.0003 (19)	−0.001 (2)	−0.0079 (19)
C14	0.039 (3)	0.040 (3)	0.029 (2)	0.009 (2)	−0.008 (2)	−0.002 (2)
C15	0.027 (2)	0.018 (2)	0.029 (2)	−0.0045 (17)	0.0021 (18)	−0.0069 (17)
C16	0.037 (2)	0.021 (2)	0.032 (3)	−0.0034 (17)	−0.007 (2)	−0.003 (2)
C17	0.060 (4)	0.025 (2)	0.022 (2)	−0.008 (2)	0.003 (2)	−0.0034 (19)
C18	0.042 (3)	0.025 (2)	0.035 (3)	0.0017 (19)	0.014 (2)	−0.006 (2)
C19	0.035 (3)	0.021 (2)	0.042 (3)	0.005 (2)	0.000 (2)	−0.005 (2)
C20	0.034 (3)	0.020 (2)	0.025 (2)	−0.0043 (18)	0.0059 (19)	−0.0005 (17)
C21	0.050 (3)	0.033 (3)	0.048 (3)	0.000 (2)	−0.021 (3)	−0.001 (2)
C22	0.071 (5)	0.045 (4)	0.055 (4)	0.011 (3)	0.027 (4)	−0.006 (3)
C23	0.051 (3)	0.033 (3)	0.030 (3)	−0.005 (2)	0.002 (2)	0.004 (2)
C24	0.026 (2)	0.025 (2)	0.023 (2)	−0.0027 (18)	−0.0068 (18)	0.0032 (18)
C25	0.027 (2)	0.031 (2)	0.028 (2)	0.0016 (18)	−0.008 (2)	−0.001 (2)
C26	0.034 (3)	0.049 (3)	0.022 (2)	0.000 (2)	−0.004 (2)	−0.007 (2)
C27	0.036 (3)	0.046 (3)	0.023 (2)	−0.011 (2)	−0.007 (2)	0.008 (2)
C28	0.029 (2)	0.030 (2)	0.033 (2)	−0.0037 (18)	−0.011 (2)	0.009 (2)
C29	0.024 (2)	0.027 (2)	0.027 (2)	−0.0018 (18)	−0.0035 (18)	0.0002 (19)

Geometric parameters (Å, º)

I1—C24	2.107 (5)	C12—H12A	0.9800
I2—C25	2.085 (4)	C12—H12B	0.9800
S1—C1	1.695 (4)	C12—H12C	0.9800
F1—C26	1.351 (6)	C13—H13A	0.9800
F2—C27	1.350 (6)	C13—H13B	0.9800
F3—C28	1.335 (5)	C13—H13C	0.9800
F4—C29	1.346 (6)	C14—H14A	0.9800
N1—C1	1.343 (6)	C14—H14B	0.9800
N1—C2	1.490 (7)	C14—H14C	0.9800
N1—C6	1.444 (6)	C15—C16	1.391 (7)
N2—C1	1.363 (6)	C15—C20	1.391 (7)
N2—C5	1.500 (7)	C16—C17	1.393 (8)
N2—C15	1.445 (6)	C16—C21	1.503 (7)
C2—H2A	0.9900	C17—H17	0.9500
C2—H2B	0.9900	C17—C18	1.361 (8)
C2—C3	1.477 (9)	C18—C19	1.395 (9)
C3—H3A	0.9900	C18—C22	1.514 (8)
C3—H3B	0.9900	C19—H19	0.9500
C3—C4	1.510 (10)	C19—C20	1.402 (7)
C4—H4A	0.9900	C20—C23	1.496 (6)
C4—H4B	0.9900	C21—H21A	0.9800
C4—C5	1.532 (8)	C21—H21B	0.9800
C5—H5A	0.9900	C21—H21C	0.9800
C5—H5B	0.9900	C22—H22A	0.9800
C6—C7	1.396 (6)	C22—H22B	0.9800
C6—C11	1.389 (7)	C22—H22C	0.9800
C7—C8	1.383 (6)	C23—H23A	0.9800
C7—C12	1.517 (6)	C23—H23B	0.9800
C8—H8	0.9500	C23—H23C	0.9800
C8—C9	1.393 (6)	C24—C25	1.398 (7)
C9—C10	1.390 (6)	C24—C29	1.381 (6)
C9—C13	1.514 (6)	C25—C26	1.382 (8)
C10—H10	0.9500	C26—C27	1.382 (8)
C10—C11	1.400 (7)	C27—C28	1.374 (8)
C11—C14	1.515 (7)	C28—C29	1.378 (7)
C1—N1—C2	120.8 (4)	H13B—C13—H13C	109.5
C1—N1—C6	121.2 (4)	C11—C14—H14A	109.5
C6—N1—C2	116.4 (4)	C11—C14—H14B	109.5
C1—N2—C5	127.0 (4)	C11—C14—H14C	109.5
C1—N2—C15	119.0 (4)	H14A—C14—H14B	109.5
C15—N2—C5	113.1 (4)	H14A—C14—H14C	109.5
N1—C1—S1	119.7 (3)	H14B—C14—H14C	109.5
N1—C1—N2	118.7 (4)	C16—C15—N2	118.1 (4)
N2—C1—S1	121.6 (3)	C16—C15—C20	122.4 (4)
N1—C2—H2A	109.5	C20—C15—N2	119.5 (4)
N1—C2—H2B	109.5	C15—C16—C17	117.5 (4)
H2A—C2—H2B	108.1	C15—C16—C21	122.3 (5)
C3—C2—N1	110.8 (5)	C17—C16—C21	120.2 (5)
C3—C2—H2A	109.5	C16—C17—H17	118.7
C3—C2—H2B	109.5	C18—C17—C16	122.6 (5)
C2—C3—H3A	109.5	C18—C17—H17	118.7
C2—C3—H3B	109.5	C17—C18—C19	118.8 (5)
C2—C3—C4	110.7 (5)	C17—C18—C22	120.9 (6)
H3A—C3—H3B	108.1	C19—C18—C22	120.3 (5)
C4—C3—H3A	109.5	C18—C19—H19	119.3
C4—C3—H3B	109.5	C18—C19—C20	121.4 (5)
C3—C4—H4A	109.2	C20—C19—H19	119.3
C3—C4—H4B	109.2	C15—C20—C19	117.3 (4)
C3—C4—C5	112.1 (6)	C15—C20—C23	120.6 (5)
H4A—C4—H4B	107.9	C19—C20—C23	122.1 (5)
C5—C4—H4A	109.2	C16—C21—H21A	109.5
C5—C4—H4B	109.2	C16—C21—H21B	109.5
N2—C5—C4	114.3 (5)	C16—C21—H21C	109.5
N2—C5—H5A	108.7	H21A—C21—H21B	109.5
N2—C5—H5B	108.7	H21A—C21—H21C	109.5
C4—C5—H5A	108.7	H21B—C21—H21C	109.5
C4—C5—H5B	108.7	C18—C22—H22A	109.5
H5A—C5—H5B	107.6	C18—C22—H22B	109.5
C7—C6—N1	118.1 (4)	C18—C22—H22C	109.5
C11—C6—N1	120.4 (4)	H22A—C22—H22B	109.5
C11—C6—C7	121.5 (4)	H22A—C22—H22C	109.5
C6—C7—C12	121.6 (4)	H22B—C22—H22C	109.5
C8—C7—C6	118.2 (4)	C20—C23—H23A	109.5
C8—C7—C12	120.2 (4)	C20—C23—H23B	109.5
C7—C8—H8	119.0	C20—C23—H23C	109.5
C7—C8—C9	122.1 (4)	H23A—C23—H23B	109.5
C9—C8—H8	119.0	H23A—C23—H23C	109.5
C8—C9—C13	121.3 (4)	H23B—C23—H23C	109.5
C10—C9—C8	118.7 (4)	C25—C24—I1	123.3 (3)
C10—C9—C13	120.0 (4)	C29—C24—I1	118.2 (4)
C9—C10—H10	119.6	C29—C24—C25	118.4 (4)
C9—C10—C11	120.7 (4)	C24—C25—I2	123.0 (4)
C11—C10—H10	119.6	C26—C25—I2	117.6 (4)
C6—C11—C10	118.9 (4)	C26—C25—C24	119.4 (4)
C6—C11—C14	121.4 (4)	F1—C26—C25	120.8 (5)
C10—C11—C14	119.7 (4)	F1—C26—C27	118.2 (5)
C7—C12—H12A	109.5	C25—C26—C27	121.1 (5)
C7—C12—H12B	109.5	F2—C27—C26	120.1 (5)
C7—C12—H12C	109.5	F2—C27—C28	120.1 (5)
H12A—C12—H12B	109.5	C28—C27—C26	119.8 (5)
H12A—C12—H12C	109.5	F3—C28—C27	119.8 (5)
H12B—C12—H12C	109.5	F3—C28—C29	121.0 (5)
C9—C13—H13A	109.5	C27—C28—C29	119.2 (4)
C9—C13—H13B	109.5	F4—C29—C24	120.9 (4)
C9—C13—H13C	109.5	F4—C29—C28	117.0 (4)
H13A—C13—H13B	109.5	C28—C29—C24	122.1 (5)
H13A—C13—H13C	109.5
I1—C24—C25—I2	−1.4 (6)	C6—C7—C8—C9	−1.4 (7)
I1—C24—C25—C26	179.2 (4)	C7—C6—C11—C10	0.1 (7)
I1—C24—C29—F4	0.3 (6)	C7—C6—C11—C14	179.3 (4)
I1—C24—C29—C28	−178.6 (3)	C7—C8—C9—C10	1.2 (7)
I2—C25—C26—F1	−1.0 (6)	C7—C8—C9—C13	−176.6 (4)
I2—C25—C26—C27	179.8 (4)	C8—C9—C10—C11	−0.3 (6)
F1—C26—C27—F2	0.2 (8)	C9—C10—C11—C6	−0.3 (7)
F1—C26—C27—C28	−179.8 (4)	C9—C10—C11—C14	−179.5 (4)
F2—C27—C28—F3	1.1 (7)	C11—C6—C7—C8	0.7 (7)
F2—C27—C28—C29	−178.7 (4)	C11—C6—C7—C12	−176.3 (4)
F3—C28—C29—F4	0.5 (7)	C12—C7—C8—C9	175.6 (4)
F3—C28—C29—C24	179.4 (4)	C13—C9—C10—C11	177.5 (4)
N1—C2—C3—C4	49.8 (7)	C15—N2—C1—S1	9.1 (6)
N1—C6—C7—C8	−176.6 (4)	C15—N2—C1—N1	−168.7 (4)
N1—C6—C7—C12	6.4 (6)	C15—N2—C5—C4	−149.6 (5)
N1—C6—C11—C10	177.4 (4)	C15—C16—C17—C18	1.0 (7)
N1—C6—C11—C14	−3.4 (7)	C16—C15—C20—C19	0.1 (7)
N2—C15—C16—C17	−178.3 (4)	C16—C15—C20—C23	−179.6 (5)
N2—C15—C16—C21	2.1 (7)	C16—C17—C18—C19	−0.1 (8)
N2—C15—C20—C19	177.4 (4)	C16—C17—C18—C22	179.8 (5)
N2—C15—C20—C23	−2.4 (7)	C17—C18—C19—C20	−0.9 (8)
C1—N1—C2—C3	−89.4 (6)	C18—C19—C20—C15	0.8 (7)
C1—N1—C6—C7	−96.7 (5)	C18—C19—C20—C23	−179.4 (5)
C1—N1—C6—C11	85.9 (6)	C20—C15—C16—C17	−1.0 (7)
C1—N2—C5—C4	18.8 (9)	C20—C15—C16—C21	179.4 (5)
C1—N2—C15—C16	−94.9 (5)	C21—C16—C17—C18	−179.4 (5)
C1—N2—C15—C20	87.7 (6)	C22—C18—C19—C20	179.3 (5)
C2—N1—C1—S1	−156.4 (4)	C24—C25—C26—F1	178.4 (4)
C2—N1—C1—N2	21.5 (7)	C24—C25—C26—C27	−0.8 (8)
C2—N1—C6—C7	69.0 (6)	C25—C24—C29—F4	178.3 (4)
C2—N1—C6—C11	−108.4 (5)	C25—C24—C29—C28	−0.6 (7)
C2—C3—C4—C5	37.8 (7)	C25—C26—C27—F2	179.4 (5)
C3—C4—C5—N2	−77.5 (7)	C25—C26—C27—C28	−0.5 (8)
C5—N2—C1—S1	−158.7 (5)	C26—C27—C28—F3	−178.9 (5)
C5—N2—C1—N1	23.5 (8)	C26—C27—C28—C29	1.3 (7)
C5—N2—C15—C16	74.4 (6)	C27—C28—C29—F4	−179.7 (4)
C5—N2—C15—C20	−102.9 (6)	C27—C28—C29—C24	−0.7 (7)
C6—N1—C1—S1	8.7 (6)	C29—C24—C25—I2	−179.3 (3)
C6—N1—C1—N2	−173.5 (4)	C29—C24—C25—C26	1.3 (7)
C6—N1—C2—C3	104.9 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···I2^i	0.99	3.11	4.041 (6)	156
C3—H3A···S1^ii	0.99	2.94	3.553 (7)	121

Symmetry codes: (i) −x+1, −y+1, z+1/2; (ii) x−1, y, z.

(SDiazMesS_13F4DIB)

Crystal data

C6F4I2·C23H30N2S	Dx = 1.756 Mg m^−3
Mr = 768.41	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 9581 reflections
a = 8.2080 (2) Å	θ = 2.6–27.9°
b = 12.9974 (2) Å	µ = 2.28 mm^−1
c = 27.2463 (5) Å	T = 100 K
V = 2906.71 (10) Å^3	Plate, colourless
Z = 4	0.15 × 0.14 × 0.06 mm
F(000) = 1504

Data collection

Bruker D8 Venture Photon 2 diffractometer	6327 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.048
φ and ω scans	θmax = 27.9°, θmin = 2.2°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −10→10
Tmin = 0.676, Tmax = 0.746	k = −16→17
28002 measured reflections	l = −35→31
6938 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.065	w = 1/[σ^2(Fo^2) + 4.5084P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.003
6938 reflections	Δρmax = 1.19 e Å^−3
386 parameters	Δρmin = −1.17 e Å^−3
96 restraints	Absolute structure: Flack x determined using 2576 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Primary atom site location: dual	Absolute structure parameter: −0.034 (12)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
I1	0.72165 (5)	0.71205 (3)	0.36743 (2)	0.03059 (9)
I2	0.28742 (5)	0.44799 (3)	0.23911 (2)	0.02999 (9)
S1	0.38379 (16)	0.55747 (11)	0.62884 (5)	0.0240 (3)
F1	0.4971 (4)	0.6342 (2)	0.28025 (13)	0.0298 (7)
F2	0.3666 (5)	0.2966 (3)	0.32949 (15)	0.0427 (9)
F3	0.5470 (5)	0.3215 (3)	0.41109 (15)	0.0463 (10)
F4	0.6986 (5)	0.5001 (3)	0.42899 (12)	0.0389 (9)
N1	0.7080 (6)	0.5521 (3)	0.63944 (18)	0.0288 (10)
N2	0.6053 (7)	0.5177 (6)	0.5619 (2)	0.058 (2)
C1	0.5786 (7)	0.5417 (4)	0.6089 (2)	0.0233 (12)
C2	0.8852 (14)	0.5164 (10)	0.6369 (5)	0.030 (2)	0.510 (7)
H2A	0.917659	0.487585	0.669107	0.036*	0.510 (7)
H2B	0.956323	0.576191	0.629945	0.036*	0.510 (7)
C3	0.9092 (18)	0.4348 (12)	0.5970 (6)	0.031 (3)	0.510 (7)
H3A	1.015656	0.400442	0.601853	0.037*	0.510 (7)
H3B	0.822798	0.381987	0.599927	0.037*	0.510 (7)
C4	0.9034 (14)	0.4823 (9)	0.5461 (4)	0.027 (2)	0.510 (7)
H4A	1.012990	0.508179	0.537313	0.032*	0.510 (7)
H4B	0.872475	0.428972	0.521937	0.032*	0.510 (7)
C5	0.7836 (16)	0.5690 (8)	0.5439 (4)	0.030 (2)	0.510 (7)
H5A	0.775333	0.596302	0.510067	0.035*	0.510 (7)
H5B	0.816622	0.625470	0.566135	0.035*	0.510 (7)
C2B	0.8708 (13)	0.5653 (10)	0.6136 (5)	0.024 (2)	0.490 (7)
H2BA	0.853487	0.599897	0.581682	0.028*	0.490 (7)
H2BB	0.942581	0.609549	0.633787	0.028*	0.490 (7)
C3B	0.9516 (18)	0.4642 (12)	0.6054 (6)	0.030 (3)	0.490 (7)
H3BA	0.982292	0.433786	0.637347	0.036*	0.490 (7)
H3BB	1.052396	0.474594	0.586036	0.036*	0.490 (7)
C4B	0.8362 (15)	0.3886 (10)	0.5774 (5)	0.032 (2)	0.490 (7)
H4BA	0.902446	0.335138	0.560865	0.038*	0.490 (7)
H4BB	0.763823	0.353813	0.601234	0.038*	0.490 (7)
C5B	0.7367 (14)	0.4419 (9)	0.5407 (4)	0.028 (2)	0.490 (7)
H5BA	0.680560	0.389637	0.520424	0.033*	0.490 (7)
H5BB	0.810095	0.481192	0.518833	0.033*	0.490 (7)
C6	0.6830 (6)	0.5884 (4)	0.6890 (2)	0.0253 (12)
C7	0.6641 (6)	0.5181 (4)	0.7277 (2)	0.0268 (13)
C8	0.6443 (7)	0.5562 (4)	0.7747 (2)	0.0264 (12)
H8	0.629387	0.509315	0.801016	0.032*
C9	0.6455 (7)	0.6609 (4)	0.7845 (2)	0.0250 (12)
C10	0.6681 (6)	0.7292 (4)	0.7457 (2)	0.0225 (11)
H10	0.671676	0.801041	0.752120	0.027*
C11	0.6856 (6)	0.6944 (4)	0.6979 (2)	0.0238 (12)
C12	0.6601 (8)	0.4038 (4)	0.7170 (3)	0.0384 (16)
H12A	0.634878	0.366094	0.747192	0.058*
H12B	0.766637	0.381772	0.704549	0.058*
H12C	0.576350	0.389436	0.692283	0.058*
C13	0.6139 (8)	0.7015 (5)	0.8355 (2)	0.0331 (13)
H13A	0.498515	0.719717	0.838755	0.050*
H13B	0.681079	0.762621	0.841258	0.050*
H13C	0.641479	0.648420	0.859691	0.050*
C14	0.7039 (8)	0.7698 (4)	0.6561 (2)	0.0270 (11)
H14A	0.684578	0.839749	0.668227	0.040*
H14B	0.624609	0.753501	0.630401	0.040*
H14C	0.814380	0.765075	0.642694	0.040*
C15	0.4722 (8)	0.5122 (5)	0.5274 (2)	0.0359 (16)
C16	0.4306 (7)	0.6010 (5)	0.5012 (2)	0.0271 (12)
C17	0.3094 (7)	0.5933 (4)	0.4660 (2)	0.0247 (12)
H17	0.280361	0.652823	0.447691	0.030*
C18	0.2287 (9)	0.5011 (4)	0.45642 (19)	0.0318 (13)
C19	0.2730 (14)	0.4165 (4)	0.4837 (2)	0.060 (3)
H19	0.218225	0.353156	0.478079	0.072*
C20	0.3945 (14)	0.4200 (5)	0.5190 (2)	0.064 (3)
C21	0.5113 (10)	0.7025 (6)	0.5113 (3)	0.061 (3)
H21A	0.622371	0.701617	0.498051	0.091*
H21B	0.515298	0.714420	0.546756	0.091*
H21C	0.449006	0.757707	0.495524	0.091*
C22	0.1001 (9)	0.4945 (6)	0.4175 (3)	0.0475 (19)
H22A	0.151699	0.482333	0.385559	0.071*
H22B	0.038801	0.559110	0.416410	0.071*
H22C	0.025815	0.437585	0.425006	0.071*
C23	0.4338 (18)	0.3246 (7)	0.5483 (4)	0.098 (4)
H23A	0.406654	0.336193	0.582895	0.148*
H23B	0.550209	0.309059	0.545316	0.148*
H23C	0.370026	0.266516	0.535742	0.148*
C24	0.5972 (7)	0.5728 (4)	0.3551 (2)	0.0256 (12)
C25	0.5066 (7)	0.5573 (4)	0.3129 (2)	0.0257 (11)
C26	0.4261 (7)	0.4664 (4)	0.3028 (2)	0.0254 (12)
C27	0.4402 (7)	0.3877 (4)	0.3370 (2)	0.0289 (13)
C28	0.5315 (8)	0.3993 (5)	0.3790 (2)	0.0331 (14)
C29	0.6091 (7)	0.4919 (5)	0.3880 (2)	0.0299 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01829 (15)	0.03687 (18)	0.03661 (19)	−0.00262 (16)	−0.00186 (18)	−0.01513 (16)
I2	0.02082 (16)	0.03148 (17)	0.03767 (19)	−0.00311 (16)	−0.00479 (18)	−0.00969 (15)
S1	0.0176 (6)	0.0285 (6)	0.0259 (6)	−0.0019 (5)	0.0054 (5)	−0.0071 (6)
F1	0.0252 (18)	0.0272 (16)	0.0371 (19)	−0.0005 (14)	−0.0047 (15)	−0.0017 (14)
F2	0.041 (2)	0.0337 (19)	0.054 (2)	−0.0142 (17)	−0.0010 (19)	−0.0026 (18)
F3	0.046 (2)	0.052 (2)	0.040 (2)	−0.0082 (19)	0.004 (2)	0.0146 (18)
F4	0.029 (2)	0.065 (2)	0.0229 (16)	−0.0045 (19)	0.0019 (17)	−0.0071 (15)
N1	0.017 (2)	0.023 (2)	0.046 (3)	0.001 (2)	0.006 (2)	−0.013 (2)
N2	0.031 (3)	0.124 (6)	0.018 (3)	0.048 (4)	0.008 (2)	0.018 (3)
C1	0.023 (3)	0.019 (3)	0.027 (3)	0.010 (2)	0.007 (2)	0.010 (2)
C2	0.018 (5)	0.042 (6)	0.030 (5)	0.006 (4)	−0.002 (5)	−0.007 (5)
C3	0.019 (5)	0.038 (6)	0.034 (5)	0.007 (4)	−0.001 (5)	−0.006 (5)
C4	0.018 (4)	0.037 (5)	0.025 (4)	0.004 (4)	0.001 (4)	−0.008 (4)
C5	0.026 (5)	0.038 (5)	0.024 (5)	−0.001 (5)	0.002 (5)	−0.005 (4)
C2B	0.010 (4)	0.038 (6)	0.023 (5)	0.001 (4)	−0.001 (4)	−0.006 (5)
C3B	0.018 (5)	0.043 (6)	0.031 (5)	0.006 (4)	−0.005 (4)	−0.011 (5)
C4B	0.023 (5)	0.038 (5)	0.035 (5)	0.008 (4)	−0.005 (4)	−0.010 (4)
C5B	0.023 (5)	0.034 (5)	0.025 (4)	0.011 (4)	−0.004 (4)	−0.017 (4)
C6	0.017 (3)	0.024 (3)	0.035 (3)	0.002 (2)	0.000 (2)	−0.010 (2)
C7	0.015 (2)	0.018 (2)	0.047 (4)	−0.0013 (19)	−0.005 (2)	0.002 (2)
C8	0.021 (3)	0.023 (3)	0.035 (3)	0.002 (2)	−0.004 (2)	0.011 (2)
C9	0.017 (3)	0.026 (3)	0.032 (3)	0.002 (2)	−0.003 (2)	0.000 (2)
C10	0.018 (2)	0.017 (2)	0.032 (3)	−0.0024 (18)	−0.001 (2)	0.001 (2)
C11	0.015 (3)	0.023 (3)	0.033 (3)	−0.0048 (19)	0.000 (2)	−0.004 (2)
C12	0.032 (3)	0.020 (3)	0.064 (5)	−0.001 (2)	−0.007 (3)	0.000 (3)
C13	0.033 (3)	0.035 (3)	0.031 (3)	0.003 (3)	−0.006 (3)	0.005 (3)
C14	0.026 (3)	0.022 (2)	0.033 (3)	−0.007 (2)	0.002 (3)	−0.001 (2)
C15	0.039 (4)	0.054 (4)	0.015 (3)	0.031 (3)	0.009 (3)	0.010 (3)
C16	0.019 (3)	0.041 (3)	0.021 (3)	−0.001 (2)	0.002 (2)	0.011 (3)
C17	0.024 (3)	0.025 (2)	0.025 (3)	0.004 (2)	0.000 (2)	0.003 (2)
C18	0.041 (4)	0.034 (3)	0.021 (2)	−0.004 (3)	0.009 (3)	−0.003 (2)
C19	0.133 (9)	0.026 (3)	0.020 (3)	−0.014 (4)	0.012 (5)	−0.002 (2)
C20	0.146 (9)	0.027 (3)	0.017 (3)	0.035 (4)	0.009 (4)	−0.001 (3)
C21	0.062 (5)	0.084 (6)	0.035 (4)	−0.051 (5)	−0.021 (4)	0.030 (4)
C22	0.042 (4)	0.064 (5)	0.036 (4)	−0.022 (4)	0.004 (3)	−0.012 (3)
C23	0.175 (8)	0.061 (5)	0.060 (5)	0.040 (5)	−0.008 (6)	0.009 (4)
C24	0.016 (2)	0.026 (3)	0.034 (3)	−0.002 (2)	0.003 (2)	−0.012 (2)
C25	0.019 (3)	0.028 (3)	0.030 (3)	0.000 (2)	0.002 (2)	−0.005 (2)
C26	0.018 (3)	0.029 (3)	0.029 (3)	0.000 (2)	0.000 (2)	−0.007 (2)
C27	0.017 (3)	0.030 (3)	0.040 (3)	−0.007 (2)	0.003 (3)	−0.008 (3)
C28	0.032 (3)	0.041 (3)	0.026 (3)	−0.006 (3)	0.004 (3)	0.003 (3)
C29	0.019 (3)	0.046 (4)	0.024 (3)	0.000 (2)	0.001 (2)	−0.007 (3)

Geometric parameters (Å, º)

I1—C24	2.106 (5)	C8—C9	1.386 (8)
I2—C26	2.090 (6)	C9—C10	1.393 (8)
S1—C1	1.701 (6)	C9—C13	1.511 (8)
F1—C25	1.340 (7)	C10—H10	0.9500
F2—C27	1.345 (6)	C10—C11	1.386 (8)
F3—C28	1.343 (7)	C11—C14	1.509 (7)
F4—C29	1.340 (7)	C12—H12A	0.9800
N1—C1	1.355 (7)	C12—H12B	0.9800
N1—C2	1.528 (12)	C12—H12C	0.9800
N1—C2B	1.520 (12)	C13—H13A	0.9800
N1—C6	1.446 (7)	C13—H13B	0.9800
N2—C1	1.338 (8)	C13—H13C	0.9800
N2—C5	1.682 (14)	C14—H14A	0.9800
N2—C5B	1.570 (11)	C14—H14B	0.9800
N2—C15	1.442 (9)	C14—H14C	0.9800
C2—H2A	0.9900	C15—C16	1.399 (8)
C2—H2B	0.9900	C15—C20	1.378 (11)
C2—C3	1.532 (18)	C16—C17	1.387 (8)
C3—H3A	0.9900	C16—C21	1.501 (9)
C3—H3B	0.9900	C17—H17	0.9500
C3—C4	1.519 (19)	C17—C18	1.394 (8)
C4—H4A	0.9900	C18—C19	1.376 (9)
C4—H4B	0.9900	C18—C22	1.499 (10)
C4—C5	1.496 (15)	C19—H19	0.9500
C5—H5A	0.9900	C19—C20	1.386 (13)
C5—H5B	0.9900	C20—C23	1.510 (10)
C2B—H2BA	0.9900	C21—H21A	0.9800
C2B—H2BB	0.9900	C21—H21B	0.9800
C2B—C3B	1.489 (19)	C21—H21C	0.9800
C3B—H3BA	0.9900	C22—H22A	0.9800
C3B—H3BB	0.9900	C22—H22B	0.9800
C3B—C4B	1.564 (18)	C22—H22C	0.9800
C4B—H4BA	0.9900	C23—H23A	0.9800
C4B—H4BB	0.9900	C23—H23B	0.9800
C4B—C5B	1.464 (16)	C23—H23C	0.9800
C5B—H5BA	0.9900	C24—C25	1.385 (8)
C5B—H5BB	0.9900	C24—C29	1.385 (8)
C6—C7	1.403 (8)	C25—C26	1.381 (8)
C6—C11	1.398 (7)	C26—C27	1.388 (8)
C7—C8	1.383 (8)	C27—C28	1.378 (9)
C7—C12	1.514 (7)	C28—C29	1.383 (8)
C8—H8	0.9500
C1—N1—C2	133.5 (6)	C6—C11—C14	120.7 (5)
C1—N1—C2B	114.6 (6)	C10—C11—C6	118.8 (5)
C1—N1—C6	119.6 (5)	C10—C11—C14	120.4 (4)
C6—N1—C2	106.0 (6)	C7—C12—H12A	109.5
C6—N1—C2B	121.4 (6)	C7—C12—H12B	109.5
C1—N2—C5	109.2 (7)	C7—C12—H12C	109.5
C1—N2—C5B	127.6 (6)	H12A—C12—H12B	109.5
C1—N2—C15	120.7 (5)	H12A—C12—H12C	109.5
C15—N2—C5	119.3 (6)	H12B—C12—H12C	109.5
C15—N2—C5B	104.5 (6)	C9—C13—H13A	109.5
N1—C1—S1	121.9 (4)	C9—C13—H13B	109.5
N2—C1—S1	119.2 (5)	C9—C13—H13C	109.5
N2—C1—N1	118.9 (5)	H13A—C13—H13B	109.5
N1—C2—H2A	109.4	H13A—C13—H13C	109.5
N1—C2—H2B	109.4	H13B—C13—H13C	109.5
N1—C2—C3	111.4 (10)	C11—C14—H14A	109.5
H2A—C2—H2B	108.0	C11—C14—H14B	109.5
C3—C2—H2A	109.4	C11—C14—H14C	109.5
C3—C2—H2B	109.4	H14A—C14—H14B	109.5
C2—C3—H3A	109.4	H14A—C14—H14C	109.5
C2—C3—H3B	109.4	H14B—C14—H14C	109.5
H3A—C3—H3B	108.0	C16—C15—N2	118.5 (7)
C4—C3—C2	111.2 (12)	C20—C15—N2	120.1 (6)
C4—C3—H3A	109.4	C20—C15—C16	121.3 (6)
C4—C3—H3B	109.4	C15—C16—C21	121.6 (6)
C3—C4—H4A	109.4	C17—C16—C15	117.9 (6)
C3—C4—H4B	109.4	C17—C16—C21	120.4 (5)
H4A—C4—H4B	108.0	C16—C17—H17	118.9
C5—C4—C3	111.4 (10)	C16—C17—C18	122.2 (5)
C5—C4—H4A	109.4	C18—C17—H17	118.9
C5—C4—H4B	109.4	C17—C18—C22	121.1 (5)
N2—C5—H5A	110.7	C19—C18—C17	117.5 (6)
N2—C5—H5B	110.7	C19—C18—C22	121.5 (6)
C4—C5—N2	105.2 (8)	C18—C19—H19	118.7
C4—C5—H5A	110.7	C18—C19—C20	122.6 (7)
C4—C5—H5B	110.7	C20—C19—H19	118.7
H5A—C5—H5B	108.8	C15—C20—C19	118.5 (6)
N1—C2B—H2BA	109.4	C15—C20—C23	121.8 (9)
N1—C2B—H2BB	109.4	C19—C20—C23	119.6 (9)
H2BA—C2B—H2BB	108.0	C16—C21—H21A	109.5
C3B—C2B—N1	111.3 (10)	C16—C21—H21B	109.5
C3B—C2B—H2BA	109.4	C16—C21—H21C	109.5
C3B—C2B—H2BB	109.4	H21A—C21—H21B	109.5
C2B—C3B—H3BA	109.4	H21A—C21—H21C	109.5
C2B—C3B—H3BB	109.4	H21B—C21—H21C	109.5
C2B—C3B—C4B	111.0 (11)	C18—C22—H22A	109.5
H3BA—C3B—H3BB	108.0	C18—C22—H22B	109.5
C4B—C3B—H3BA	109.4	C18—C22—H22C	109.5
C4B—C3B—H3BB	109.4	H22A—C22—H22B	109.5
C3B—C4B—H4BA	109.2	H22A—C22—H22C	109.5
C3B—C4B—H4BB	109.2	H22B—C22—H22C	109.5
H4BA—C4B—H4BB	107.9	C20—C23—H23A	109.5
C5B—C4B—C3B	111.9 (11)	C20—C23—H23B	109.5
C5B—C4B—H4BA	109.2	C20—C23—H23C	109.5
C5B—C4B—H4BB	109.2	H23A—C23—H23B	109.5
N2—C5B—H5BA	108.4	H23A—C23—H23C	109.5
N2—C5B—H5BB	108.4	H23B—C23—H23C	109.5
C4B—C5B—N2	115.5 (8)	C25—C24—I1	121.2 (4)
C4B—C5B—H5BA	108.4	C25—C24—C29	117.8 (5)
C4B—C5B—H5BB	108.4	C29—C24—I1	121.0 (4)
H5BA—C5B—H5BB	107.5	F1—C25—C24	118.3 (5)
C7—C6—N1	120.3 (5)	F1—C25—C26	118.5 (5)
C11—C6—N1	118.7 (5)	C26—C25—C24	123.1 (5)
C11—C6—C7	121.0 (5)	C25—C26—I2	121.6 (4)
C6—C7—C12	119.9 (6)	C25—C26—C27	117.2 (5)
C8—C7—C6	118.3 (5)	C27—C26—I2	121.2 (4)
C8—C7—C12	121.8 (5)	F2—C27—C26	120.7 (5)
C7—C8—H8	119.0	F2—C27—C28	117.8 (6)
C7—C8—C9	122.0 (5)	C28—C27—C26	121.5 (5)
C9—C8—H8	119.0	F3—C28—C27	120.6 (6)
C8—C9—C10	118.8 (5)	F3—C28—C29	119.8 (6)
C8—C9—C13	121.3 (5)	C27—C28—C29	119.6 (6)
C10—C9—C13	119.9 (5)	F4—C29—C24	121.1 (5)
C9—C10—H10	119.4	F4—C29—C28	118.0 (6)
C11—C10—C9	121.2 (5)	C28—C29—C24	120.8 (6)
C11—C10—H10	119.4
I1—C24—C25—F1	−1.4 (7)	C5B—N2—C1—N1	38.2 (12)
I1—C24—C25—C26	178.5 (4)	C5B—N2—C15—C16	−116.4 (7)
I1—C24—C29—F4	0.8 (8)	C5B—N2—C15—C20	60.3 (9)
I1—C24—C29—C28	−177.8 (4)	C6—N1—C1—S1	−6.8 (7)
I2—C26—C27—F2	1.0 (8)	C6—N1—C1—N2	173.6 (6)
I2—C26—C27—C28	179.9 (5)	C6—N1—C2—C3	154.3 (10)
F1—C25—C26—I2	−1.3 (7)	C6—N1—C2B—C3B	112.5 (10)
F1—C25—C26—C27	179.1 (5)	C6—C7—C8—C9	−1.1 (8)
F2—C27—C28—F3	0.5 (9)	C7—C6—C11—C10	−0.4 (8)
F2—C27—C28—C29	−180.0 (5)	C7—C6—C11—C14	−179.2 (5)
F3—C28—C29—F4	0.3 (9)	C7—C8—C9—C10	−0.3 (8)
F3—C28—C29—C24	179.0 (5)	C7—C8—C9—C13	176.4 (5)
N1—C2—C3—C4	73.6 (13)	C8—C9—C10—C11	1.4 (8)
N1—C2B—C3B—C4B	54.3 (15)	C9—C10—C11—C6	−1.1 (8)
N1—C6—C7—C8	178.5 (5)	C9—C10—C11—C14	177.8 (5)
N1—C6—C7—C12	−3.5 (8)	C11—C6—C7—C8	1.5 (8)
N1—C6—C11—C10	−177.5 (5)	C11—C6—C7—C12	179.5 (5)
N1—C6—C11—C14	3.7 (8)	C12—C7—C8—C9	−179.1 (5)
N2—C15—C16—C17	176.0 (5)	C13—C9—C10—C11	−175.3 (5)
N2—C15—C16—C21	−5.2 (9)	C15—N2—C1—S1	4.4 (10)
N2—C15—C20—C19	−176.5 (7)	C15—N2—C1—N1	−176.0 (6)
N2—C15—C20—C23	5.8 (12)	C15—N2—C5—C4	−115.3 (8)
C1—N1—C2—C3	−14.5 (16)	C15—N2—C5B—C4B	−147.3 (9)
C1—N1—C2B—C3B	−91.1 (11)	C15—C16—C17—C18	0.5 (9)
C1—N1—C6—C7	94.5 (6)	C16—C15—C20—C19	0.0 (11)
C1—N1—C6—C11	−88.4 (6)	C16—C15—C20—C23	−177.7 (8)
C1—N2—C5—C4	100.0 (8)	C16—C17—C18—C19	0.3 (9)
C1—N2—C5B—C4B	2.8 (15)	C16—C17—C18—C22	−178.9 (6)
C1—N2—C15—C16	91.0 (8)	C17—C18—C19—C20	−1.0 (11)
C1—N2—C15—C20	−92.4 (9)	C18—C19—C20—C15	0.8 (12)
C2—N1—C1—S1	160.8 (8)	C18—C19—C20—C23	178.6 (9)
C2—N1—C1—N2	−18.8 (12)	C20—C15—C16—C17	−0.6 (9)
C2—N1—C6—C7	−76.2 (8)	C20—C15—C16—C21	178.2 (7)
C2—N1—C6—C11	100.9 (7)	C21—C16—C17—C18	−178.4 (6)
C2—C3—C4—C5	−35.3 (15)	C22—C18—C19—C20	178.3 (7)
C3—C4—C5—N2	−56.6 (12)	C24—C25—C26—I2	178.8 (4)
C5—N2—C1—S1	148.5 (5)	C24—C25—C26—C27	−0.8 (8)
C5—N2—C1—N1	−31.9 (8)	C25—C24—C29—F4	178.0 (5)
C5—N2—C15—C16	−49.6 (9)	C25—C24—C29—C28	−0.6 (9)
C5—N2—C15—C20	127.0 (8)	C25—C26—C27—F2	−179.3 (5)
C2B—N1—C1—S1	−163.7 (6)	C25—C26—C27—C28	−0.4 (9)
C2B—N1—C1—N2	16.7 (9)	C26—C27—C28—F3	−178.4 (5)
C2B—N1—C6—C7	−110.2 (8)	C26—C27—C28—C29	1.1 (9)
C2B—N1—C6—C11	66.8 (9)	C27—C28—C29—F4	−179.2 (5)
C2B—C3B—C4B—C5B	36.4 (17)	C27—C28—C29—C24	−0.5 (9)
C3B—C4B—C5B—N2	−67.7 (14)	C29—C24—C25—F1	−178.6 (5)
C5B—N2—C1—S1	−141.4 (8)	C29—C24—C25—C26	1.3 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···I2^i	0.99	3.19	3.897 (12)	129
C5—H5A···F4	0.99	2.62	3.330 (11)	129
C2B—H2BB···I1^ii	0.99	3.26	4.115 (12)	146
C4B—H4BA···F3^iii	0.99	2.48	3.247 (13)	134
C5B—H5BB···F4	0.99	2.62	3.153 (12)	114

Symmetry codes: (i) −x+3/2, −y+1, z+1/2; (ii) x+1/2, −y+3/2, −z+1; (iii) x+1/2, −y+1/2, −z+1.

(SDiazMesSe_13F4DIB)

Crystal data

C6F4I2·C23H30N2Se	Dx = 1.854 Mg m^−3
Mr = 815.31	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 9905 reflections
a = 8.2583 (2) Å	θ = 2.7–29.1°
b = 12.9953 (4) Å	µ = 3.45 mm^−1
c = 27.2240 (7) Å	T = 100 K
V = 2921.66 (14) Å^3	Needle, yellow
Z = 4	0.29 × 0.08 × 0.07 mm
F(000) = 1576

Data collection

Bruker D8 Venture Photon 2 diffractometer	7491 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.047
φ and ω scans	θmax = 29.2°, θmin = 2.2°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −11→11
Tmin = 0.494, Tmax = 0.746	k = −17→17
85940 measured reflections	l = −37→37
7878 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.022	H-atom parameters constrained
wR(F^2) = 0.044	w = 1/[σ^2(Fo^2) + (0.003P)^2 + 3.3501P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max = 0.002
7878 reflections	Δρmax = 0.99 e Å^−3
386 parameters	Δρmin = −0.93 e Å^−3
96 restraints	Absolute structure: Flack x determined using 3173 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Primary atom site location: dual	Absolute structure parameter: 0.003 (4)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
I1	0.27596 (3)	0.29294 (2)	0.63147 (2)	0.02633 (6)
I2	0.71345 (3)	0.55910 (2)	0.75697 (2)	0.02496 (6)
F1	0.5058 (3)	0.37188 (18)	0.71659 (9)	0.0262 (5)
F2	0.6203 (3)	0.7124 (2)	0.66793 (10)	0.0363 (6)
F3	0.4328 (3)	0.6878 (2)	0.58820 (10)	0.0386 (6)
F4	0.2851 (3)	0.5070 (2)	0.57072 (8)	0.0332 (5)
C24	0.3959 (4)	0.4341 (3)	0.64289 (13)	0.0235 (8)
C25	0.4907 (4)	0.4498 (3)	0.68425 (13)	0.0219 (7)
C26	0.5686 (4)	0.5413 (3)	0.69417 (14)	0.0222 (8)
C27	0.5482 (5)	0.6211 (3)	0.66093 (16)	0.0257 (8)
C28	0.4536 (5)	0.6091 (3)	0.61945 (15)	0.0277 (9)
C29	0.3786 (5)	0.5152 (3)	0.61094 (14)	0.0255 (8)
Se1	0.62295 (4)	0.44453 (3)	0.36976 (2)	0.02102 (7)
N1	0.2846 (4)	0.4467 (2)	0.35880 (11)	0.0230 (6)
N2	0.3779 (5)	0.4732 (4)	0.43772 (12)	0.0470 (13)
C1	0.4077 (4)	0.4559 (3)	0.39017 (14)	0.0215 (8)
C2	0.1093 (7)	0.4809 (5)	0.3622 (2)	0.0233 (12)	0.666 (6)
H2A	0.040599	0.420804	0.370225	0.028*	0.666 (6)
H2B	0.074185	0.507833	0.329880	0.028*	0.666 (6)
C2B	0.1201 (13)	0.4345 (11)	0.3849 (5)	0.023 (2)	0.334 (6)
H2BA	0.048660	0.389895	0.364883	0.028*	0.334 (6)
H2BB	0.136618	0.400630	0.417075	0.028*	0.334 (6)
C3	0.0847 (9)	0.5641 (6)	0.4012 (3)	0.0265 (15)	0.666 (6)
H3A	−0.020467	0.598705	0.395531	0.032*	0.666 (6)
H3B	0.171209	0.616428	0.398036	0.032*	0.666 (6)
C3B	0.0418 (19)	0.5342 (13)	0.3924 (6)	0.030 (3)	0.334 (6)
H3BA	−0.060481	0.524206	0.410743	0.036*	0.334 (6)
H3BB	0.014680	0.564709	0.360069	0.036*	0.334 (6)
C4	0.0875 (7)	0.5190 (5)	0.4538 (2)	0.0260 (13)	0.666 (6)
H4A	0.115889	0.573826	0.477525	0.031*	0.666 (6)
H4B	−0.021244	0.492515	0.462324	0.031*	0.666 (6)
C4B	0.1534 (15)	0.6094 (10)	0.4213 (5)	0.028 (2)	0.334 (6)
H4BA	0.227076	0.644530	0.398010	0.033*	0.334 (6)
H4BB	0.085977	0.662624	0.437391	0.033*	0.334 (6)
C5	0.2094 (7)	0.4333 (5)	0.4571 (2)	0.0263 (12)	0.666 (6)
H5A	0.173015	0.374101	0.437033	0.032*	0.666 (6)
H5B	0.219903	0.410228	0.491575	0.032*	0.666 (6)
C5B	0.2507 (11)	0.5557 (9)	0.4590 (4)	0.021 (2)	0.334 (6)
H5BA	0.176108	0.519821	0.481759	0.025*	0.334 (6)
H5BB	0.310895	0.607671	0.478310	0.025*	0.334 (6)
C6	0.3124 (4)	0.4087 (3)	0.30952 (14)	0.0219 (8)
C7	0.3325 (4)	0.4783 (3)	0.27094 (15)	0.0229 (8)
C8	0.3573 (4)	0.4394 (3)	0.22411 (14)	0.0236 (7)
H8	0.373662	0.485822	0.197604	0.028*
C9	0.3589 (4)	0.3340 (3)	0.21503 (15)	0.0230 (8)
C10	0.3339 (4)	0.2666 (3)	0.25432 (14)	0.0211 (7)
H10	0.331605	0.194597	0.248373	0.025*
C11	0.3125 (4)	0.3025 (3)	0.30155 (14)	0.0207 (7)
C12	0.3350 (5)	0.5931 (3)	0.28009 (18)	0.0315 (9)
H12A	0.364071	0.628992	0.249681	0.047*
H12B	0.414888	0.608996	0.305599	0.047*
H12C	0.227546	0.615763	0.290918	0.047*
C13	0.3971 (5)	0.2921 (4)	0.16454 (14)	0.0298 (9)
H13A	0.512893	0.276216	0.162425	0.045*
H13B	0.369190	0.343679	0.139659	0.045*
H13C	0.334055	0.229403	0.158799	0.045*
C14	0.2923 (5)	0.2282 (3)	0.34377 (13)	0.0247 (8)
H14A	0.305584	0.157613	0.331807	0.037*
H14B	0.184077	0.236286	0.358011	0.037*
H14C	0.374250	0.242609	0.368896	0.037*
C15	0.5092 (5)	0.4841 (4)	0.47293 (14)	0.0311 (10)
C16	0.5579 (5)	0.3969 (3)	0.49871 (14)	0.0244 (8)
C17	0.6793 (4)	0.4082 (3)	0.53392 (13)	0.0218 (7)
H17	0.713417	0.349488	0.551919	0.026*
C18	0.7517 (5)	0.5024 (3)	0.54354 (14)	0.0282 (9)
C19	0.6960 (8)	0.5872 (3)	0.51675 (15)	0.0439 (13)
H19	0.743101	0.652631	0.522803	0.053*
C20	0.5748 (8)	0.5795 (4)	0.48174 (15)	0.0467 (15)
C21	0.4880 (6)	0.2928 (4)	0.48822 (17)	0.0470 (14)
H21A	0.381028	0.287134	0.503588	0.070*
H21B	0.559652	0.239573	0.501566	0.070*
H21C	0.477480	0.283502	0.452632	0.070*
C22	0.8818 (6)	0.5125 (4)	0.58174 (17)	0.0424 (12)
H22A	0.832079	0.517811	0.614320	0.064*
H22B	0.946063	0.574377	0.575193	0.064*
H22C	0.952234	0.451821	0.580633	0.064*
C23	0.5156 (11)	0.6723 (5)	0.4540 (2)	0.078 (2)
H23A	0.504030	0.654997	0.419186	0.117*
H23B	0.593769	0.728508	0.457698	0.117*
H23C	0.410504	0.693811	0.467221	0.117*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01752 (10)	0.03178 (12)	0.02970 (12)	−0.00316 (10)	−0.00131 (11)	−0.01204 (11)
I2	0.01775 (10)	0.02832 (12)	0.02883 (11)	−0.00328 (11)	−0.00286 (10)	−0.00732 (10)
F1	0.0233 (11)	0.0248 (12)	0.0305 (12)	−0.0024 (9)	−0.0045 (10)	−0.0002 (10)
F2	0.0377 (14)	0.0279 (13)	0.0431 (15)	−0.0091 (12)	−0.0031 (12)	0.0004 (12)
F3	0.0416 (15)	0.0416 (16)	0.0325 (14)	−0.0014 (12)	0.0008 (12)	0.0105 (12)
F4	0.0283 (12)	0.0520 (15)	0.0194 (10)	−0.0012 (13)	−0.0029 (11)	−0.0050 (10)
C24	0.0156 (15)	0.029 (2)	0.0258 (18)	−0.0004 (15)	0.0019 (13)	−0.0095 (16)
C25	0.0167 (16)	0.0230 (18)	0.0259 (18)	0.0019 (15)	0.0024 (14)	−0.0038 (15)
C26	0.0148 (16)	0.029 (2)	0.0226 (17)	−0.0007 (15)	−0.0001 (14)	−0.0047 (16)
C27	0.0204 (18)	0.0238 (19)	0.033 (2)	−0.0057 (15)	0.0026 (16)	−0.0041 (16)
C28	0.027 (2)	0.032 (2)	0.024 (2)	0.0003 (17)	0.0048 (16)	0.0032 (16)
C29	0.0182 (18)	0.037 (2)	0.0208 (18)	0.0013 (16)	0.0009 (15)	−0.0056 (16)
Se1	0.01567 (15)	0.02645 (17)	0.02095 (16)	0.00002 (14)	0.00397 (14)	−0.00476 (16)
N1	0.0147 (12)	0.0203 (14)	0.0340 (16)	−0.0003 (14)	0.0048 (13)	−0.0078 (13)
N2	0.0238 (18)	0.102 (4)	0.0154 (16)	0.033 (2)	0.0069 (14)	0.0153 (19)
C1	0.0190 (17)	0.0197 (19)	0.0258 (18)	0.0057 (14)	0.0058 (14)	0.0081 (15)
C2	0.014 (2)	0.031 (3)	0.025 (3)	0.004 (2)	0.001 (2)	−0.008 (2)
C2B	0.014 (4)	0.030 (5)	0.026 (5)	0.001 (4)	0.003 (4)	−0.004 (5)
C3	0.020 (3)	0.026 (3)	0.033 (3)	0.008 (3)	0.001 (3)	−0.007 (3)
C3B	0.023 (5)	0.038 (6)	0.030 (5)	0.001 (5)	−0.005 (4)	−0.005 (5)
C4	0.019 (3)	0.033 (3)	0.025 (3)	0.003 (2)	0.002 (2)	−0.007 (2)
C4B	0.021 (5)	0.033 (5)	0.029 (5)	0.008 (4)	−0.001 (4)	−0.004 (4)
C5	0.021 (2)	0.036 (3)	0.022 (2)	0.000 (3)	0.007 (2)	−0.002 (2)
C5B	0.013 (4)	0.027 (4)	0.023 (4)	0.006 (4)	0.001 (3)	−0.009 (4)
C6	0.0169 (18)	0.0200 (17)	0.0288 (19)	0.0008 (13)	−0.0008 (14)	−0.0028 (14)
C7	0.0131 (16)	0.0184 (17)	0.037 (2)	−0.0002 (13)	−0.0037 (14)	0.0021 (15)
C8	0.0156 (16)	0.0246 (18)	0.0306 (18)	0.0001 (15)	−0.0045 (14)	0.0095 (17)
C9	0.0143 (16)	0.027 (2)	0.0274 (19)	0.0008 (14)	−0.0021 (15)	0.0019 (15)
C10	0.0182 (16)	0.0167 (16)	0.0282 (19)	−0.0012 (12)	−0.0017 (14)	−0.0004 (14)
C11	0.0160 (17)	0.0187 (17)	0.0274 (18)	−0.0006 (13)	0.0008 (13)	−0.0004 (14)
C12	0.030 (2)	0.0177 (18)	0.046 (3)	−0.0007 (16)	−0.0076 (19)	0.0017 (17)
C13	0.031 (2)	0.033 (2)	0.026 (2)	0.0060 (19)	−0.0028 (16)	0.0015 (18)
C14	0.0270 (19)	0.0206 (18)	0.0264 (18)	−0.0060 (17)	−0.0001 (17)	0.0004 (14)
C15	0.035 (2)	0.043 (2)	0.0156 (18)	0.023 (2)	0.0082 (16)	0.0065 (17)
C16	0.0182 (17)	0.036 (2)	0.0193 (18)	0.0012 (16)	0.0028 (15)	0.0084 (16)
C17	0.0186 (17)	0.0261 (18)	0.0206 (17)	0.0046 (14)	0.0005 (13)	0.0042 (14)
C18	0.034 (3)	0.030 (2)	0.0205 (17)	−0.0034 (17)	0.0062 (16)	−0.0021 (15)
C19	0.086 (4)	0.0214 (19)	0.025 (2)	−0.008 (2)	0.013 (3)	0.0013 (16)
C20	0.091 (4)	0.032 (3)	0.0165 (19)	0.031 (3)	0.011 (2)	0.0029 (17)
C21	0.052 (3)	0.062 (3)	0.027 (2)	−0.033 (3)	−0.016 (2)	0.020 (2)
C22	0.035 (3)	0.057 (3)	0.035 (2)	−0.016 (2)	0.001 (2)	−0.011 (2)
C23	0.149 (6)	0.043 (3)	0.042 (3)	0.044 (4)	−0.001 (4)	0.003 (2)

Geometric parameters (Å, º)

I1—C24	2.108 (4)	C5B—H5BB	0.9900
I2—C26	2.100 (4)	C6—C7	1.396 (5)
F1—C25	1.348 (5)	C6—C11	1.397 (5)
F2—C27	1.340 (5)	C7—C8	1.387 (6)
F3—C28	1.342 (5)	C7—C12	1.513 (6)
F4—C29	1.344 (4)	C8—H8	0.9500
C24—C25	1.386 (5)	C8—C9	1.392 (6)
C24—C29	1.374 (6)	C9—C10	1.398 (5)
C25—C26	1.378 (5)	C9—C13	1.512 (6)
C26—C27	1.387 (6)	C10—H10	0.9500
C27—C28	1.382 (6)	C10—C11	1.379 (5)
C28—C29	1.388 (6)	C11—C14	1.510 (5)
Se1—C1	1.868 (4)	C12—H12A	0.9800
N1—C1	1.333 (5)	C12—H12B	0.9800
N1—C2	1.517 (6)	C12—H12C	0.9800
N1—C2B	1.541 (11)	C13—H13A	0.9800
N1—C6	1.448 (5)	C13—H13B	0.9800
N2—C1	1.337 (5)	C13—H13C	0.9800
N2—C5	1.575 (7)	C14—H14A	0.9800
N2—C5B	1.608 (10)	C14—H14B	0.9800
N2—C15	1.455 (6)	C14—H14C	0.9800
C2—H2A	0.9900	C15—C16	1.392 (5)
C2—H2B	0.9900	C15—C20	1.373 (7)
C2—C3	1.529 (9)	C16—C17	1.394 (5)
C2B—H2BA	0.9900	C16—C21	1.499 (7)
C2B—H2BB	0.9900	C17—H17	0.9500
C2B—C3B	1.46 (2)	C17—C18	1.387 (6)
C3—H3A	0.9900	C18—C19	1.399 (6)
C3—H3B	0.9900	C18—C22	1.501 (6)
C3—C4	1.547 (10)	C19—H19	0.9500
C3B—H3BA	0.9900	C19—C20	1.386 (8)
C3B—H3BB	0.9900	C20—C23	1.504 (7)
C3B—C4B	1.558 (19)	C21—H21A	0.9800
C4—H4A	0.9900	C21—H21B	0.9800
C4—H4B	0.9900	C21—H21C	0.9800
C4—C5	1.504 (8)	C22—H22A	0.9800
C4B—H4BA	0.9900	C22—H22B	0.9800
C4B—H4BB	0.9900	C22—H22C	0.9800
C4B—C5B	1.479 (16)	C23—H23A	0.9800
C5—H5A	0.9900	C23—H23B	0.9800
C5—H5B	0.9900	C23—H23C	0.9800
C5B—H5BA	0.9900
C25—C24—I1	120.9 (3)	C4B—C5B—H5BA	108.6
C29—C24—I1	121.7 (3)	C4B—C5B—H5BB	108.6
C29—C24—C25	117.4 (4)	H5BA—C5B—H5BB	107.5
F1—C25—C24	118.2 (4)	C7—C6—N1	119.7 (3)
F1—C25—C26	118.5 (3)	C7—C6—C11	121.6 (4)
C26—C25—C24	123.4 (4)	C11—C6—N1	118.7 (3)
C25—C26—I2	121.4 (3)	C6—C7—C12	121.1 (4)
C25—C26—C27	117.4 (3)	C8—C7—C6	118.2 (3)
C27—C26—I2	121.2 (3)	C8—C7—C12	120.6 (4)
F2—C27—C26	121.0 (4)	C7—C8—H8	119.2
F2—C27—C28	117.9 (4)	C7—C8—C9	121.6 (4)
C28—C27—C26	121.1 (4)	C9—C8—H8	119.2
F3—C28—C27	120.3 (4)	C8—C9—C10	118.6 (4)
F3—C28—C29	120.5 (4)	C8—C9—C13	121.2 (4)
C27—C28—C29	119.2 (4)	C10—C9—C13	120.1 (4)
F4—C29—C24	121.0 (4)	C9—C10—H10	119.3
F4—C29—C28	117.6 (4)	C11—C10—C9	121.4 (3)
C24—C29—C28	121.5 (4)	C11—C10—H10	119.3
C1—N1—C2	131.5 (4)	C6—C11—C14	120.9 (3)
C1—N1—C2B	112.7 (5)	C10—C11—C6	118.6 (4)
C1—N1—C6	120.2 (3)	C10—C11—C14	120.5 (3)
C6—N1—C2	107.9 (3)	C7—C12—H12A	109.5
C6—N1—C2B	122.1 (5)	C7—C12—H12B	109.5
C1—N2—C5	115.6 (4)	C7—C12—H12C	109.5
C1—N2—C5B	125.5 (5)	H12A—C12—H12B	109.5
C1—N2—C15	121.1 (3)	H12A—C12—H12C	109.5
C15—N2—C5	118.1 (3)	H12B—C12—H12C	109.5
C15—N2—C5B	100.6 (5)	C9—C13—H13A	109.5
N1—C1—Se1	121.9 (3)	C9—C13—H13B	109.5
N1—C1—N2	119.7 (3)	C9—C13—H13C	109.5
N2—C1—Se1	118.5 (3)	H13A—C13—H13B	109.5
N1—C2—H2A	109.2	H13A—C13—H13C	109.5
N1—C2—H2B	109.2	H13B—C13—H13C	109.5
N1—C2—C3	112.1 (5)	C11—C14—H14A	109.5
H2A—C2—H2B	107.9	C11—C14—H14B	109.5
C3—C2—H2A	109.2	C11—C14—H14C	109.5
C3—C2—H2B	109.2	H14A—C14—H14B	109.5
N1—C2B—H2BA	109.4	H14A—C14—H14C	109.5
N1—C2B—H2BB	109.4	H14B—C14—H14C	109.5
H2BA—C2B—H2BB	108.0	C16—C15—N2	117.9 (4)
C3B—C2B—N1	111.3 (11)	C20—C15—N2	119.8 (4)
C3B—C2B—H2BA	109.4	C20—C15—C16	122.2 (4)
C3B—C2B—H2BB	109.4	C15—C16—C17	117.9 (4)
C2—C3—H3A	109.2	C15—C16—C21	121.8 (4)
C2—C3—H3B	109.2	C17—C16—C21	120.2 (4)
C2—C3—C4	111.9 (6)	C16—C17—H17	118.9
H3A—C3—H3B	107.9	C18—C17—C16	122.2 (4)
C4—C3—H3A	109.2	C18—C17—H17	118.9
C4—C3—H3B	109.2	C17—C18—C19	117.0 (4)
C2B—C3B—H3BA	109.4	C17—C18—C22	121.1 (4)
C2B—C3B—H3BB	109.4	C19—C18—C22	121.9 (4)
C2B—C3B—C4B	111.4 (12)	C18—C19—H19	118.7
H3BA—C3B—H3BB	108.0	C20—C19—C18	122.6 (4)
C4B—C3B—H3BA	109.4	C20—C19—H19	118.7
C4B—C3B—H3BB	109.4	C15—C20—C19	118.0 (4)
C3—C4—H4A	109.6	C15—C20—C23	120.6 (5)
C3—C4—H4B	109.6	C19—C20—C23	121.4 (5)
H4A—C4—H4B	108.1	C16—C21—H21A	109.5
C5—C4—C3	110.2 (5)	C16—C21—H21B	109.5
C5—C4—H4A	109.6	C16—C21—H21C	109.5
C5—C4—H4B	109.6	H21A—C21—H21B	109.5
C3B—C4B—H4BA	109.2	H21A—C21—H21C	109.5
C3B—C4B—H4BB	109.2	H21B—C21—H21C	109.5
H4BA—C4B—H4BB	107.9	C18—C22—H22A	109.5
C5B—C4B—C3B	112.1 (12)	C18—C22—H22B	109.5
C5B—C4B—H4BA	109.2	C18—C22—H22C	109.5
C5B—C4B—H4BB	109.2	H22A—C22—H22B	109.5
N2—C5—H5A	109.9	H22A—C22—H22C	109.5
N2—C5—H5B	109.9	H22B—C22—H22C	109.5
C4—C5—N2	109.1 (5)	C20—C23—H23A	109.5
C4—C5—H5A	109.9	C20—C23—H23B	109.5
C4—C5—H5B	109.9	C20—C23—H23C	109.5
H5A—C5—H5B	108.3	H23A—C23—H23B	109.5
N2—C5B—H5BA	108.6	H23A—C23—H23C	109.5
N2—C5B—H5BB	108.6	H23B—C23—H23C	109.5
C4B—C5B—N2	114.8 (8)
I1—C24—C25—F1	0.9 (4)	C2B—N1—C1—Se1	167.1 (6)
I1—C24—C25—C26	−178.4 (3)	C2B—N1—C1—N2	−12.5 (7)
I1—C24—C29—F4	−0.6 (5)	C2B—N1—C6—C7	110.3 (7)
I1—C24—C29—C28	177.9 (3)	C2B—N1—C6—C11	−67.4 (8)
I2—C26—C27—F2	−0.1 (5)	C2B—C3B—C4B—C5B	−35.8 (17)
I2—C26—C27—C28	179.6 (3)	C3—C4—C5—N2	53.0 (7)
F1—C25—C26—I2	1.7 (5)	C3B—C4B—C5B—N2	63.8 (13)
F1—C25—C26—C27	−178.6 (3)	C5—N2—C1—Se1	−153.2 (3)
F2—C27—C28—F3	−1.6 (6)	C5—N2—C1—N1	26.4 (6)
F2—C27—C28—C29	179.4 (4)	C5—N2—C15—C16	59.0 (6)
F3—C28—C29—F4	−0.3 (6)	C5—N2—C15—C20	−117.4 (5)
F3—C28—C29—C24	−178.8 (4)	C5B—N2—C1—Se1	134.8 (6)
C24—C25—C26—I2	−179.0 (3)	C5B—N2—C1—N1	−45.6 (8)
C24—C25—C26—C27	0.7 (6)	C5B—N2—C15—C16	122.2 (6)
C25—C24—C29—F4	−178.1 (3)	C5B—N2—C15—C20	−54.2 (6)
C25—C24—C29—C28	0.4 (6)	C6—N1—C1—Se1	11.5 (5)
C25—C26—C27—F2	−179.8 (3)	C6—N1—C1—N2	−168.1 (4)
C25—C26—C27—C28	−0.1 (6)	C6—N1—C2—C3	−153.7 (5)
C26—C27—C28—F3	178.7 (4)	C6—N1—C2B—C3B	−113.0 (10)
C26—C27—C28—C29	−0.3 (6)	C6—C7—C8—C9	1.4 (5)
C27—C28—C29—F4	178.7 (3)	C7—C6—C11—C10	0.4 (5)
C27—C28—C29—C24	0.2 (6)	C7—C6—C11—C14	179.4 (4)
C29—C24—C25—F1	178.5 (3)	C7—C8—C9—C10	0.3 (5)
C29—C24—C25—C26	−0.8 (5)	C7—C8—C9—C13	−175.9 (3)
N1—C2—C3—C4	−75.9 (7)	C8—C9—C10—C11	−1.8 (5)
N1—C2B—C3B—C4B	−56.0 (16)	C9—C10—C11—C6	1.4 (5)
N1—C6—C7—C8	−179.4 (3)	C9—C10—C11—C14	−177.5 (3)
N1—C6—C7—C12	3.4 (5)	C11—C6—C7—C8	−1.8 (5)
N1—C6—C11—C10	178.0 (3)	C11—C6—C7—C12	−179.0 (3)
N1—C6—C11—C14	−3.0 (5)	C12—C7—C8—C9	178.7 (4)
N2—C15—C16—C17	−177.4 (3)	C13—C9—C10—C11	174.4 (3)
N2—C15—C16—C21	4.8 (6)	C15—N2—C1—Se1	0.7 (6)
N2—C15—C20—C19	177.9 (4)	C15—N2—C1—N1	−179.7 (4)
N2—C15—C20—C23	−2.1 (7)	C15—N2—C5—C4	112.0 (5)
C1—N1—C2—C3	19.0 (8)	C15—N2—C5B—C4B	145.9 (9)
C1—N1—C2B—C3B	91.9 (11)	C15—C16—C17—C18	−0.3 (6)
C1—N1—C6—C7	−96.5 (4)	C16—C15—C20—C19	1.6 (7)
C1—N1—C6—C11	85.9 (4)	C16—C15—C20—C23	−178.3 (5)
C1—N2—C5—C4	−93.3 (6)	C16—C17—C18—C19	1.0 (6)
C1—N2—C5B—C4B	4.6 (12)	C16—C17—C18—C22	179.9 (4)
C1—N2—C15—C16	−94.3 (5)	C17—C18—C19—C20	−0.4 (7)
C1—N2—C15—C20	89.3 (6)	C18—C19—C20—C15	−0.8 (7)
C2—N1—C1—Se1	−160.4 (4)	C18—C19—C20—C23	179.1 (5)
C2—N1—C1—N2	20.0 (7)	C20—C15—C16—C17	−1.1 (6)
C2—N1—C6—C7	77.2 (5)	C20—C15—C16—C21	−178.8 (5)
C2—N1—C6—C11	−100.4 (4)	C21—C16—C17—C18	177.5 (4)
C2—C3—C4—C5	36.5 (7)	C22—C18—C19—C20	−179.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···I2^i	0.99	3.22	3.947 (6)	132
C2B—H2BA···I1^ii	0.99	3.28	4.124 (12)	145
C3B—H3BA···Se1^iii	0.99	3.03	3.701 (16)	127
C4B—H4BB···F3^iv	0.99	2.42	3.214 (13)	137
C5—H5B···F4	0.99	2.55	3.299 (6)	132
C5B—H5BA···F4	0.99	2.59	3.119 (11)	114

Symmetry codes: (i) −x+1/2, −y+1, z−1/2; (ii) x−1/2, −y+1/2, −z+1; (iii) x−1, y, z; (iv) x−1/2, −y+3/2, −z+1.

(2SDiazMesS_13F4DIB)

Crystal data

C6F4I2·2(C23H30N2S)	F(000) = 2296
Mr = 1134.96	Dx = 1.534 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 39.0981 (14) Å	Cell parameters from 9982 reflections
b = 17.0474 (6) Å	θ = 2.9–27.5°
c = 7.3957 (2) Å	µ = 1.42 mm^−1
β = 94.344 (1)°	T = 100 K
V = 4915.2 (3) Å^3	Needle, colourless
Z = 4	0.28 × 0.09 × 0.03 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	4240 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.060
φ and ω scans	θmax = 26.5°, θmin = 2.4°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −49→49
Tmin = 0.663, Tmax = 0.746	k = −21→21
40822 measured reflections	l = −9→9
5102 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.061	H-atom parameters constrained
S = 1.16	w = 1/[σ^2(Fo^2) + 15.3992P] where P = (Fo^2 + 2Fc^2)/3
5102 reflections	(Δ/σ)max = 0.001
334 parameters	Δρmax = 1.02 e Å^−3
0 restraints	Δρmin = −0.53 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
I1	0.43108 (2)	0.35251 (2)	0.42166 (3)	0.02373 (6)
S1	0.35833 (2)	0.29987 (4)	0.58974 (9)	0.02131 (15)
F1	0.44710 (4)	0.53387 (10)	0.3761 (2)	0.0257 (4)
F2	0.500000	0.61184 (13)	0.250000	0.0237 (5)
F3	0.500000	0.29357 (13)	0.250000	0.0248 (5)
N1	0.33552 (6)	0.30045 (13)	0.9179 (3)	0.0220 (5)
N2	0.37423 (6)	0.20126 (14)	0.8616 (3)	0.0244 (5)
C1	0.35592 (7)	0.26514 (15)	0.8030 (4)	0.0168 (5)
C2	0.32006 (15)	0.2649 (3)	1.0808 (7)	0.0235 (13)	0.585 (6)
H2A	0.295879	0.282115	1.080500	0.028*	0.585 (6)
H2B	0.332441	0.285810	1.192161	0.028*	0.585 (6)
C3	0.3210 (2)	0.1761 (4)	1.0890 (12)	0.0274 (18)	0.585 (6)
H3A	0.313511	0.154666	0.968047	0.033*	0.585 (6)
H3B	0.304668	0.157682	1.175677	0.033*	0.585 (6)
C4	0.35647 (15)	0.1447 (3)	1.1468 (8)	0.0302 (14)	0.585 (6)
H4A	0.358251	0.089520	1.106702	0.036*	0.585 (6)
H4B	0.360107	0.145804	1.280752	0.036*	0.585 (6)
C5	0.38391 (13)	0.1936 (3)	1.0653 (7)	0.0255 (13)	0.585 (6)
H5A	0.406546	0.167737	1.086297	0.031*	0.585 (6)
H5B	0.385284	0.246083	1.122474	0.031*	0.585 (6)
C2B	0.3430 (2)	0.2869 (4)	1.1210 (9)	0.0187 (16)	0.415 (6)
H2BA	0.367723	0.275730	1.148679	0.022*	0.415 (6)
H2BB	0.337008	0.334175	1.189492	0.022*	0.415 (6)
C3B	0.3218 (2)	0.2179 (5)	1.1741 (11)	0.0256 (19)	0.415 (6)
H3BA	0.297174	0.232075	1.158492	0.031*	0.415 (6)
H3BB	0.327428	0.205687	1.303768	0.031*	0.415 (6)
C4B	0.3280 (3)	0.1462 (6)	1.0615 (17)	0.027 (3)	0.415 (6)
H4BA	0.312360	0.147137	0.949966	0.032*	0.415 (6)
H4BB	0.322835	0.098549	1.131027	0.032*	0.415 (6)
C5B	0.36497 (19)	0.1422 (4)	1.0097 (9)	0.0231 (18)	0.415 (6)
H5BA	0.369478	0.088458	0.966708	0.028*	0.415 (6)
H5BB	0.380428	0.151507	1.119962	0.028*	0.415 (6)
C6	0.31698 (7)	0.37127 (15)	0.8660 (3)	0.0161 (5)
C7	0.28438 (7)	0.36464 (17)	0.7792 (4)	0.0211 (6)
C8	0.26548 (7)	0.43408 (19)	0.7480 (4)	0.0254 (7)
H8	0.243059	0.431064	0.689167	0.031*
C9	0.27856 (8)	0.50680 (17)	0.8006 (4)	0.0239 (6)
C10	0.31140 (7)	0.51029 (16)	0.8848 (4)	0.0207 (6)
H10	0.320675	0.559874	0.920887	0.025*
C11	0.33117 (7)	0.44339 (16)	0.9181 (4)	0.0178 (6)
C12	0.26957 (9)	0.28673 (19)	0.7212 (5)	0.0362 (8)
H12A	0.285394	0.259706	0.645539	0.054*
H12B	0.247512	0.294678	0.651575	0.054*
H12C	0.266138	0.254846	0.828602	0.054*
C13	0.25785 (9)	0.5806 (2)	0.7624 (4)	0.0374 (9)
H13A	0.268165	0.623924	0.834590	0.056*
H13B	0.234277	0.572193	0.794699	0.056*
H13C	0.257682	0.593540	0.633251	0.056*
C14	0.36691 (8)	0.44953 (19)	1.0078 (4)	0.0297 (7)
H14A	0.373200	0.504926	1.022632	0.045*
H14B	0.383036	0.423510	0.932149	0.045*
H14C	0.367774	0.424143	1.126908	0.045*
C15	0.39592 (7)	0.16237 (16)	0.7402 (4)	0.0218 (6)
C16	0.38176 (8)	0.10518 (17)	0.6230 (5)	0.0299 (7)
C17	0.40300 (10)	0.0695 (2)	0.5059 (5)	0.0456 (10)
H17	0.393796	0.030133	0.425396	0.055*
C18	0.43715 (10)	0.0896 (2)	0.5028 (6)	0.0457 (10)
C19	0.45059 (8)	0.14522 (19)	0.6234 (5)	0.0350 (8)
H19	0.474154	0.158744	0.623005	0.042*
C20	0.43055 (7)	0.18205 (16)	0.7458 (4)	0.0237 (6)
C21	0.34397 (9)	0.0851 (2)	0.6179 (5)	0.0414 (9)
H21A	0.338996	0.060317	0.732541	0.062*
H21B	0.338106	0.048849	0.517469	0.062*
H21C	0.330366	0.133153	0.600374	0.062*
C22	0.45948 (14)	0.0521 (3)	0.3668 (7)	0.0840 (17)
H22A	0.453036	0.072907	0.245403	0.126*
H22B	0.456155	−0.004841	0.366802	0.126*
H22C	0.483627	0.064211	0.400546	0.126*
C23	0.44581 (9)	0.24371 (19)	0.8733 (5)	0.0349 (8)
H23A	0.430741	0.289721	0.869756	0.052*
H23B	0.468416	0.258954	0.836333	0.052*
H23C	0.448195	0.222623	0.996902	0.052*
C24	0.47225 (7)	0.41115 (16)	0.3147 (4)	0.0204 (6)
C25	0.47286 (7)	0.49242 (17)	0.3131 (4)	0.0193 (6)
C26	0.500000	0.5329 (2)	0.250000	0.0194 (8)
C27	0.500000	0.3722 (2)	0.250000	0.0214 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01944 (10)	0.03001 (11)	0.02127 (10)	−0.00519 (8)	−0.00165 (7)	0.00346 (8)
S1	0.0204 (4)	0.0271 (4)	0.0168 (3)	0.0034 (3)	0.0042 (3)	0.0062 (3)
F1	0.0220 (9)	0.0300 (9)	0.0258 (9)	0.0057 (7)	0.0054 (7)	−0.0013 (7)
F2	0.0244 (13)	0.0196 (11)	0.0268 (13)	0.000	−0.0002 (10)	0.000
F3	0.0239 (13)	0.0184 (11)	0.0314 (13)	0.000	−0.0021 (10)	0.000
N1	0.0328 (14)	0.0174 (11)	0.0165 (12)	0.0048 (10)	0.0059 (10)	0.0032 (9)
N2	0.0261 (14)	0.0302 (13)	0.0177 (12)	0.0112 (11)	0.0064 (10)	0.0087 (10)
C1	0.0150 (13)	0.0185 (13)	0.0168 (13)	−0.0034 (11)	0.0009 (11)	0.0002 (10)
C2	0.029 (3)	0.022 (3)	0.021 (3)	0.006 (2)	0.011 (2)	0.005 (2)
C3	0.032 (4)	0.024 (5)	0.027 (4)	−0.004 (4)	0.012 (3)	0.009 (4)
C4	0.038 (3)	0.027 (3)	0.027 (3)	0.003 (2)	0.008 (3)	0.008 (2)
C5	0.026 (3)	0.028 (3)	0.021 (3)	−0.001 (2)	−0.004 (2)	0.007 (2)
C2B	0.021 (4)	0.020 (3)	0.015 (3)	0.003 (3)	0.002 (3)	0.000 (3)
C3B	0.032 (4)	0.024 (4)	0.022 (4)	−0.002 (3)	0.005 (3)	−0.002 (4)
C4B	0.040 (7)	0.019 (6)	0.023 (5)	−0.009 (5)	0.011 (4)	0.001 (5)
C5B	0.036 (4)	0.016 (3)	0.019 (4)	0.002 (3)	0.008 (3)	0.009 (3)
C6	0.0176 (13)	0.0177 (13)	0.0135 (13)	−0.0004 (10)	0.0048 (10)	−0.0008 (10)
C7	0.0234 (15)	0.0285 (15)	0.0116 (13)	−0.0101 (12)	0.0027 (11)	−0.0024 (11)
C8	0.0141 (14)	0.0478 (19)	0.0143 (14)	0.0058 (13)	0.0008 (11)	−0.0001 (13)
C9	0.0276 (16)	0.0286 (16)	0.0165 (14)	0.0111 (13)	0.0097 (12)	0.0041 (12)
C10	0.0258 (16)	0.0176 (13)	0.0196 (14)	0.0012 (12)	0.0071 (12)	0.0002 (11)
C11	0.0156 (14)	0.0232 (14)	0.0150 (13)	0.0006 (11)	0.0035 (11)	−0.0006 (11)
C12	0.0283 (18)	0.0412 (19)	0.040 (2)	−0.0110 (15)	0.0059 (15)	−0.0160 (15)
C13	0.042 (2)	0.047 (2)	0.0244 (17)	0.0255 (17)	0.0113 (15)	0.0092 (15)
C14	0.0197 (16)	0.0333 (17)	0.0355 (18)	−0.0001 (13)	−0.0021 (13)	−0.0083 (14)
C15	0.0232 (15)	0.0199 (14)	0.0225 (15)	0.0063 (12)	0.0033 (12)	0.0035 (11)
C16	0.0286 (17)	0.0225 (15)	0.0388 (19)	−0.0029 (13)	0.0044 (14)	0.0006 (13)
C17	0.051 (2)	0.0318 (19)	0.055 (2)	−0.0056 (17)	0.0102 (19)	−0.0204 (17)
C18	0.047 (2)	0.038 (2)	0.055 (2)	0.0083 (17)	0.0202 (19)	−0.0122 (17)
C19	0.0228 (16)	0.0325 (17)	0.051 (2)	0.0037 (14)	0.0126 (15)	0.0057 (16)
C20	0.0189 (15)	0.0196 (14)	0.0324 (17)	0.0053 (12)	0.0016 (12)	0.0033 (12)
C21	0.0305 (19)	0.0299 (18)	0.063 (3)	−0.0098 (15)	−0.0007 (17)	0.0055 (17)
C22	0.080 (4)	0.085 (4)	0.092 (4)	0.024 (3)	0.043 (3)	−0.030 (3)
C23	0.0305 (18)	0.0320 (18)	0.040 (2)	−0.0010 (14)	−0.0093 (15)	0.0007 (15)
C24	0.0176 (14)	0.0270 (15)	0.0162 (14)	−0.0043 (11)	−0.0013 (11)	0.0024 (11)
C25	0.0151 (14)	0.0292 (15)	0.0134 (13)	0.0048 (11)	0.0006 (11)	−0.0011 (11)
C26	0.023 (2)	0.0201 (19)	0.0145 (19)	0.000	−0.0054 (16)	0.000
C27	0.025 (2)	0.021 (2)	0.017 (2)	0.000	−0.0039 (16)	0.000

Geometric parameters (Å, º)

I1—C24	2.100 (3)	C8—H8	0.9500
S1—C1	1.694 (3)	C8—C9	1.385 (4)
F1—C25	1.342 (3)	C9—C10	1.386 (4)
F2—C26	1.346 (4)	C9—C13	1.511 (4)
F3—C27	1.340 (4)	C10—H10	0.9500
N1—C1	1.351 (3)	C10—C11	1.389 (4)
N1—C2	1.515 (5)	C11—C14	1.504 (4)
N1—C2B	1.526 (7)	C12—H12A	0.9800
N1—C6	1.445 (3)	C12—H12B	0.9800
N2—C1	1.356 (3)	C12—H12C	0.9800
N2—C5	1.531 (5)	C13—H13A	0.9800
N2—C5B	1.551 (6)	C13—H13B	0.9800
N2—C15	1.442 (3)	C13—H13C	0.9800
C2—H2A	0.9900	C14—H14A	0.9800
C2—H2B	0.9900	C14—H14B	0.9800
C2—C3	1.515 (8)	C14—H14C	0.9800
C3—H3A	0.9900	C15—C16	1.391 (4)
C3—H3B	0.9900	C15—C20	1.393 (4)
C3—C4	1.517 (10)	C16—C17	1.385 (5)
C4—H4A	0.9900	C16—C21	1.514 (4)
C4—H4B	0.9900	C17—H17	0.9500
C4—C5	1.519 (7)	C17—C18	1.380 (5)
C5—H5A	0.9900	C18—C19	1.378 (5)
C5—H5B	0.9900	C18—C22	1.522 (5)
C2B—H2BA	0.9900	C19—H19	0.9500
C2B—H2BB	0.9900	C19—C20	1.391 (4)
C2B—C3B	1.508 (10)	C20—C23	1.505 (4)
C3B—H3BA	0.9900	C21—H21A	0.9800
C3B—H3BB	0.9900	C21—H21B	0.9800
C3B—C4B	1.510 (11)	C21—H21C	0.9800
C4B—H4BA	0.9900	C22—H22A	0.9800
C4B—H4BB	0.9900	C22—H22B	0.9800
C4B—C5B	1.523 (13)	C22—H22C	0.9800
C5B—H5BA	0.9900	C23—H23A	0.9800
C5B—H5BB	0.9900	C23—H23B	0.9800
C6—C7	1.388 (4)	C23—H23C	0.9800
C6—C11	1.391 (4)	C24—C25	1.386 (4)
C7—C8	1.405 (4)	C24—C27	1.388 (3)
C7—C12	1.499 (4)	C25—C26	1.377 (3)
C1—N1—C2	127.8 (3)	C9—C10—H10	119.0
C1—N1—C2B	118.2 (3)	C9—C10—C11	121.9 (3)
C1—N1—C6	120.9 (2)	C11—C10—H10	119.0
C6—N1—C2	108.9 (3)	C6—C11—C14	121.4 (2)
C6—N1—C2B	116.3 (3)	C10—C11—C6	118.1 (3)
C1—N2—C5	118.0 (3)	C10—C11—C14	120.4 (3)
C1—N2—C5B	127.0 (3)	C7—C12—H12A	109.5
C1—N2—C15	119.4 (2)	C7—C12—H12B	109.5
C15—N2—C5	117.4 (3)	C7—C12—H12C	109.5
C15—N2—C5B	108.7 (3)	H12A—C12—H12B	109.5
N1—C1—S1	120.5 (2)	H12A—C12—H12C	109.5
N1—C1—N2	118.6 (2)	H12B—C12—H12C	109.5
N2—C1—S1	120.9 (2)	C9—C13—H13A	109.5
N1—C2—H2A	108.5	C9—C13—H13B	109.5
N1—C2—H2B	108.5	C9—C13—H13C	109.5
N1—C2—C3	115.0 (5)	H13A—C13—H13B	109.5
H2A—C2—H2B	107.5	H13A—C13—H13C	109.5
C3—C2—H2A	108.5	H13B—C13—H13C	109.5
C3—C2—H2B	108.5	C11—C14—H14A	109.5
C2—C3—H3A	109.1	C11—C14—H14B	109.5
C2—C3—H3B	109.1	C11—C14—H14C	109.5
C2—C3—C4	112.5 (6)	H14A—C14—H14B	109.5
H3A—C3—H3B	107.8	H14A—C14—H14C	109.5
C4—C3—H3A	109.1	H14B—C14—H14C	109.5
C4—C3—H3B	109.1	C16—C15—N2	119.0 (3)
C3—C4—H4A	109.5	C16—C15—C20	121.8 (3)
C3—C4—H4B	109.5	C20—C15—N2	119.1 (3)
C3—C4—C5	110.6 (5)	C15—C16—C21	121.0 (3)
H4A—C4—H4B	108.1	C17—C16—C15	117.9 (3)
C5—C4—H4A	109.5	C17—C16—C21	121.0 (3)
C5—C4—H4B	109.5	C16—C17—H17	119.1
N2—C5—H5A	110.1	C18—C17—C16	121.9 (3)
N2—C5—H5B	110.1	C18—C17—H17	119.1
C4—C5—N2	107.9 (4)	C17—C18—C22	120.7 (4)
C4—C5—H5A	110.1	C19—C18—C17	118.8 (3)
C4—C5—H5B	110.1	C19—C18—C22	120.5 (4)
H5A—C5—H5B	108.4	C18—C19—H19	119.1
N1—C2B—H2BA	110.1	C18—C19—C20	121.7 (3)
N1—C2B—H2BB	110.1	C20—C19—H19	119.1
H2BA—C2B—H2BB	108.5	C15—C20—C23	121.7 (3)
C3B—C2B—N1	107.8 (6)	C19—C20—C15	117.8 (3)
C3B—C2B—H2BA	110.1	C19—C20—C23	120.5 (3)
C3B—C2B—H2BB	110.1	C16—C21—H21A	109.5
C2B—C3B—H3BA	109.2	C16—C21—H21B	109.5
C2B—C3B—H3BB	109.2	C16—C21—H21C	109.5
C2B—C3B—C4B	111.9 (8)	H21A—C21—H21B	109.5
H3BA—C3B—H3BB	107.9	H21A—C21—H21C	109.5
C4B—C3B—H3BA	109.2	H21B—C21—H21C	109.5
C4B—C3B—H3BB	109.2	C18—C22—H22A	109.5
C3B—C4B—H4BA	109.3	C18—C22—H22B	109.5
C3B—C4B—H4BB	109.3	C18—C22—H22C	109.5
C3B—C4B—C5B	111.8 (9)	H22A—C22—H22B	109.5
H4BA—C4B—H4BB	107.9	H22A—C22—H22C	109.5
C5B—C4B—H4BA	109.3	H22B—C22—H22C	109.5
C5B—C4B—H4BB	109.3	C20—C23—H23A	109.5
N2—C5B—H5BA	108.5	C20—C23—H23B	109.5
N2—C5B—H5BB	108.5	C20—C23—H23C	109.5
C4B—C5B—N2	115.2 (6)	H23A—C23—H23B	109.5
C4B—C5B—H5BA	108.5	H23A—C23—H23C	109.5
C4B—C5B—H5BB	108.5	H23B—C23—H23C	109.5
H5BA—C5B—H5BB	107.5	C25—C24—I1	119.6 (2)
C7—C6—N1	118.6 (2)	C25—C24—C27	117.5 (3)
C7—C6—C11	122.2 (3)	C27—C24—I1	122.9 (2)
C11—C6—N1	118.9 (2)	F1—C25—C24	120.6 (2)
C6—C7—C8	117.4 (3)	F1—C25—C26	118.1 (3)
C6—C7—C12	121.7 (3)	C26—C25—C24	121.2 (3)
C8—C7—C12	120.8 (3)	F2—C26—C25^i	120.09 (18)
C7—C8—H8	119.0	F2—C26—C25	120.09 (18)
C9—C8—C7	122.0 (3)	C25^i—C26—C25	119.8 (4)
C9—C8—H8	119.0	F3—C27—C24^i	118.60 (18)
C8—C9—C10	118.3 (3)	F3—C27—C24	118.60 (18)
C8—C9—C13	120.8 (3)	C24^i—C27—C24	122.8 (4)
C10—C9—C13	120.9 (3)
I1—C24—C25—F1	−1.3 (4)	C5B—N2—C1—N1	27.1 (5)
I1—C24—C25—C26	177.69 (16)	C5B—N2—C15—C16	70.7 (4)
I1—C24—C27—F3	2.4 (2)	C5B—N2—C15—C20	−108.1 (4)
I1—C24—C27—C24^i	−177.6 (2)	C6—N1—C1—S1	−3.9 (4)
F1—C25—C26—F2	−1.0 (3)	C6—N1—C1—N2	176.4 (2)
F1—C25—C26—C25^i	179.0 (3)	C6—N1—C2—C3	147.0 (5)
N1—C2—C3—C4	75.7 (7)	C6—N1—C2B—C3B	111.3 (5)
N1—C2B—C3B—C4B	55.0 (9)	C6—C7—C8—C9	0.2 (4)
N1—C6—C7—C8	173.2 (2)	C7—C6—C11—C10	1.5 (4)
N1—C6—C7—C12	−6.5 (4)	C7—C6—C11—C14	−178.4 (3)
N1—C6—C11—C10	−173.0 (2)	C7—C8—C9—C10	0.6 (4)
N1—C6—C11—C14	7.2 (4)	C7—C8—C9—C13	179.0 (3)
N2—C15—C16—C17	179.1 (3)	C8—C9—C10—C11	−0.3 (4)
N2—C15—C16—C21	1.7 (4)	C9—C10—C11—C6	−0.7 (4)
N2—C15—C20—C19	−178.1 (3)	C9—C10—C11—C14	179.2 (3)
N2—C15—C20—C23	−0.9 (4)	C11—C6—C7—C8	−1.2 (4)
C1—N1—C2—C3	−15.0 (7)	C11—C6—C7—C12	179.1 (3)
C1—N1—C2B—C3B	−92.4 (6)	C12—C7—C8—C9	179.9 (3)
C1—N1—C6—C7	89.4 (3)	C13—C9—C10—C11	−178.7 (3)
C1—N1—C6—C11	−96.0 (3)	C15—N2—C1—S1	−0.2 (4)
C1—N2—C5—C4	93.5 (4)	C15—N2—C1—N1	179.4 (3)
C1—N2—C5B—C4B	15.0 (9)	C15—N2—C5—C4	−112.2 (4)
C1—N2—C15—C16	−86.2 (3)	C15—N2—C5B—C4B	−139.7 (6)
C1—N2—C15—C20	94.9 (3)	C15—C16—C17—C18	−0.4 (6)
C2—N1—C1—S1	156.2 (4)	C16—C15—C20—C19	3.0 (4)
C2—N1—C1—N2	−23.4 (5)	C16—C15—C20—C23	−179.8 (3)
C2—N1—C6—C7	−74.1 (4)	C16—C17—C18—C19	1.8 (6)
C2—N1—C6—C11	100.6 (4)	C16—C17—C18—C22	−177.2 (4)
C2—C3—C4—C5	−37.8 (8)	C17—C18—C19—C20	−0.8 (6)
C3—C4—C5—N2	−50.3 (6)	C18—C19—C20—C15	−1.5 (5)
C5—N2—C1—S1	153.5 (3)	C18—C19—C20—C23	−178.8 (3)
C5—N2—C1—N1	−26.8 (4)	C20—C15—C16—C17	−2.1 (5)
C5—N2—C15—C16	119.9 (3)	C20—C15—C16—C21	−179.5 (3)
C5—N2—C15—C20	−58.9 (4)	C21—C16—C17—C18	177.0 (4)
C2B—N1—C1—S1	−159.1 (4)	C22—C18—C19—C20	178.2 (4)
C2B—N1—C1—N2	21.3 (5)	C24—C25—C26—F2	−179.96 (19)
C2B—N1—C6—C7	−114.9 (4)	C24—C25—C26—C25^i	0.04 (19)
C2B—N1—C6—C11	59.7 (4)	C25—C24—C27—F3	−179.96 (18)
C2B—C3B—C4B—C5B	33.3 (11)	C25—C24—C27—C24^i	0.03 (18)
C3B—C4B—C5B—N2	−73.5 (10)	C27—C24—C25—F1	−179.0 (2)
C5B—N2—C1—S1	−152.5 (4)	C27—C24—C25—C26	−0.1 (4)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···I1^ii	0.99	3.29	4.117 (5)	143
C3B—H3BB···S1^ii	0.99	2.85	3.574 (9)	131

Symmetry code: (ii) x, y, z+1.

(2SDiazMesSe_13F4DIB)

Crystal data

C6F4I2·2(C23H30N2Se)	F(000) = 2440
Mr = 1228.76	Dx = 1.635 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 39.058 (4) Å	Cell parameters from 9751 reflections
b = 17.2429 (14) Å	θ = 2.6–26.4°
c = 7.4287 (6) Å	µ = 2.77 mm^−1
β = 94.012 (4)°	T = 100 K
V = 4990.8 (7) Å^3	Needle, colourless
Z = 4	0.39 × 0.04 × 0.04 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	4119 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.068
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −48→48
Tmin = 0.623, Tmax = 0.745	k = −21→21
52044 measured reflections	l = −9→9
4907 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.068	H-atom parameters constrained
S = 1.24	w = 1/[σ^2(Fo^2) + 28.6286P] where P = (Fo^2 + 2Fc^2)/3
4907 reflections	(Δ/σ)max = 0.004
297 parameters	Δρmax = 1.00 e Å^−3
0 restraints	Δρmin = −0.67 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.56952 (2)	0.64492 (2)	0.07995 (3)	0.02015 (7)
Se1	0.35627 (2)	0.29736 (2)	0.06953 (5)	0.01597 (9)
F1	0.55294 (5)	0.46570 (12)	0.1246 (3)	0.0238 (5)
F2	0.500000	0.38868 (17)	0.250000	0.0227 (7)
F3	0.500000	0.70334 (15)	0.250000	0.0183 (6)
N1	0.33201 (7)	0.29559 (16)	0.4140 (4)	0.0144 (6)
N2	0.37567 (7)	0.20587 (17)	0.3722 (4)	0.0140 (6)
C1	0.35473 (9)	0.2633 (2)	0.3066 (5)	0.0140 (7)
C2	0.31923 (10)	0.2624 (2)	0.5824 (5)	0.0211 (8)
H2A	0.295155	0.279053	0.591365	0.025*
H2B	0.332985	0.284146	0.687409	0.025*
C3	0.32071 (10)	0.1747 (2)	0.5933 (5)	0.0238 (9)
H3A	0.313456	0.152675	0.473676	0.029*
H3B	0.304386	0.156521	0.680270	0.029*
C4	0.35652 (10)	0.1452 (2)	0.6520 (5)	0.0229 (8)
H4A	0.360097	0.147308	0.785148	0.028*
H4B	0.358796	0.090507	0.613923	0.028*
C5	0.38341 (10)	0.1943 (2)	0.5683 (5)	0.0207 (8)
H5A	0.384786	0.245425	0.628854	0.025*
H5B	0.406074	0.168809	0.588452	0.025*
C6	0.31486 (9)	0.3675 (2)	0.3627 (4)	0.0137 (7)
C7	0.33001 (9)	0.4376 (2)	0.4172 (5)	0.0162 (7)
C8	0.31130 (9)	0.5055 (2)	0.3842 (5)	0.0174 (7)
H8	0.321271	0.553833	0.420324	0.021*
C9	0.27819 (9)	0.5044 (2)	0.2992 (5)	0.0170 (7)
C10	0.26413 (9)	0.4334 (2)	0.2452 (5)	0.0178 (8)
H10	0.241727	0.432059	0.186600	0.021*
C11	0.28211 (9)	0.3638 (2)	0.2747 (5)	0.0148 (7)
C12	0.36571 (10)	0.4405 (2)	0.5095 (6)	0.0243 (9)
H12A	0.371723	0.494428	0.539357	0.036*
H12B	0.382162	0.419458	0.428612	0.036*
H12C	0.366385	0.409637	0.620396	0.036*
C13	0.25875 (10)	0.5788 (2)	0.2632 (5)	0.0234 (8)
H13A	0.259022	0.592197	0.135124	0.035*
H13B	0.269607	0.620505	0.336524	0.035*
H13C	0.234971	0.572227	0.294642	0.035*
C14	0.26633 (10)	0.2876 (2)	0.2172 (5)	0.0229 (8)
H14A	0.281620	0.260272	0.139365	0.034*
H14B	0.244150	0.296736	0.150529	0.034*
H14C	0.262911	0.255904	0.323994	0.034*
C15	0.39692 (9)	0.1641 (2)	0.2529 (5)	0.0160 (7)
C16	0.38239 (9)	0.1037 (2)	0.1458 (5)	0.0175 (8)
C17	0.40316 (10)	0.0659 (2)	0.0292 (5)	0.0194 (8)
H17	0.393791	0.024697	−0.043529	0.023*
C18	0.43728 (10)	0.0867 (2)	0.0162 (5)	0.0219 (8)
C19	0.45091 (10)	0.1452 (2)	0.1276 (5)	0.0224 (8)
H19	0.474341	0.159036	0.121011	0.027*
C20	0.43148 (9)	0.1844 (2)	0.2484 (5)	0.0175 (8)
C21	0.34484 (9)	0.0831 (2)	0.1502 (5)	0.0201 (8)
H21A	0.338914	0.043120	0.059704	0.030*
H21B	0.330833	0.129429	0.123645	0.030*
H21C	0.340436	0.063529	0.270265	0.030*
C22	0.45864 (11)	0.0468 (3)	−0.1181 (6)	0.0358 (11)
H22A	0.451621	0.065012	−0.240137	0.054*
H22B	0.455226	−0.009399	−0.111453	0.054*
H22C	0.482944	0.058920	−0.089981	0.054*
C23	0.44712 (10)	0.2494 (2)	0.3634 (6)	0.0244 (9)
H23A	0.452096	0.230761	0.487142	0.037*
H23B	0.430955	0.292836	0.363809	0.037*
H23C	0.468440	0.266629	0.313908	0.037*
C24	0.52781 (9)	0.5870 (2)	0.1851 (5)	0.0176 (8)
C25	0.52715 (9)	0.5068 (2)	0.1872 (5)	0.0169 (7)
C26	0.500000	0.4667 (3)	0.250000	0.0166 (10)
C27	0.500000	0.6255 (3)	0.250000	0.0179 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01913 (13)	0.02343 (13)	0.01757 (13)	−0.00372 (10)	−0.00106 (9)	0.00246 (10)
Se1	0.01747 (18)	0.01759 (18)	0.01312 (18)	0.00292 (14)	0.00293 (13)	0.00252 (14)
F1	0.0218 (12)	0.0249 (12)	0.0252 (12)	0.0072 (9)	0.0052 (9)	−0.0003 (10)
F2	0.0237 (16)	0.0150 (15)	0.0294 (18)	0.000	0.0012 (13)	0.000
F3	0.0233 (16)	0.0085 (13)	0.0234 (16)	0.000	0.0026 (13)	0.000
N1	0.0172 (15)	0.0132 (14)	0.0130 (15)	0.0031 (12)	0.0014 (12)	0.0007 (12)
N2	0.0157 (15)	0.0146 (14)	0.0115 (14)	0.0006 (12)	−0.0003 (11)	0.0004 (12)
C1	0.0136 (17)	0.0143 (17)	0.0140 (17)	−0.0024 (13)	−0.0001 (14)	−0.0021 (14)
C2	0.029 (2)	0.0211 (19)	0.0141 (18)	0.0051 (16)	0.0095 (16)	0.0018 (16)
C3	0.033 (2)	0.0197 (19)	0.020 (2)	0.0001 (17)	0.0118 (17)	0.0065 (16)
C4	0.035 (2)	0.0155 (18)	0.0188 (19)	0.0077 (16)	0.0071 (17)	0.0033 (16)
C5	0.028 (2)	0.0215 (19)	0.0119 (18)	0.0036 (16)	−0.0018 (15)	0.0026 (15)
C6	0.0154 (17)	0.0153 (17)	0.0107 (16)	0.0022 (14)	0.0025 (13)	−0.0011 (14)
C7	0.0184 (18)	0.0179 (18)	0.0126 (17)	0.0001 (14)	0.0021 (14)	−0.0003 (15)
C8	0.0194 (19)	0.0170 (18)	0.0161 (18)	−0.0012 (14)	0.0052 (14)	−0.0010 (15)
C9	0.0199 (18)	0.0175 (18)	0.0143 (17)	0.0015 (15)	0.0074 (14)	0.0020 (15)
C10	0.0156 (18)	0.0248 (19)	0.0126 (18)	0.0007 (15)	−0.0008 (14)	−0.0002 (15)
C11	0.0186 (18)	0.0156 (17)	0.0104 (16)	−0.0047 (14)	0.0017 (13)	0.0010 (14)
C12	0.021 (2)	0.0216 (19)	0.030 (2)	−0.0014 (16)	−0.0012 (17)	−0.0026 (17)
C13	0.030 (2)	0.0216 (19)	0.019 (2)	0.0074 (17)	0.0066 (16)	0.0041 (16)
C14	0.021 (2)	0.023 (2)	0.024 (2)	−0.0021 (16)	0.0010 (16)	−0.0071 (17)
C15	0.0180 (18)	0.0150 (17)	0.0149 (18)	0.0041 (14)	0.0010 (14)	0.0017 (14)
C16	0.0203 (19)	0.0154 (17)	0.0168 (18)	0.0015 (14)	0.0005 (15)	0.0037 (15)
C17	0.023 (2)	0.0179 (18)	0.0165 (18)	0.0030 (15)	−0.0027 (15)	−0.0020 (15)
C18	0.025 (2)	0.0244 (19)	0.0167 (19)	0.0067 (16)	0.0029 (16)	0.0013 (16)
C19	0.0161 (18)	0.027 (2)	0.024 (2)	0.0022 (16)	0.0033 (15)	0.0048 (17)
C20	0.0118 (17)	0.0193 (18)	0.0212 (19)	0.0037 (14)	−0.0006 (14)	0.0045 (16)
C21	0.0163 (19)	0.0177 (18)	0.026 (2)	0.0004 (15)	0.0021 (15)	−0.0022 (16)
C22	0.026 (2)	0.051 (3)	0.031 (2)	0.013 (2)	0.0087 (19)	−0.009 (2)
C23	0.023 (2)	0.022 (2)	0.028 (2)	−0.0061 (16)	−0.0037 (17)	−0.0004 (17)
C24	0.0161 (18)	0.0235 (19)	0.0128 (17)	−0.0051 (15)	−0.0019 (14)	0.0022 (15)
C25	0.0149 (18)	0.0208 (18)	0.0147 (17)	0.0037 (14)	−0.0015 (14)	−0.0012 (15)
C26	0.020 (3)	0.013 (2)	0.016 (3)	0.000	−0.003 (2)	0.000
C27	0.020 (3)	0.019 (3)	0.015 (3)	0.000	0.000 (2)	0.000

Geometric parameters (Å, º)

I1—C24	2.107 (4)	C12—H12A	0.9800
Se1—C1	1.861 (3)	C12—H12B	0.9800
F1—C25	1.341 (4)	C12—H12C	0.9800
F2—C26	1.345 (6)	C13—H13A	0.9800
F3—C27	1.342 (6)	C13—H13B	0.9800
N1—C1	1.354 (4)	C13—H13C	0.9800
N1—C2	1.493 (4)	C14—H14A	0.9800
N1—C6	1.448 (4)	C14—H14B	0.9800
N2—C1	1.353 (4)	C14—H14C	0.9800
N2—C5	1.480 (4)	C15—C16	1.406 (5)
N2—C15	1.448 (4)	C15—C20	1.397 (5)
C2—H2A	0.9900	C16—C17	1.390 (5)
C2—H2B	0.9900	C16—C21	1.511 (5)
C2—C3	1.514 (5)	C17—H17	0.9500
C3—H3A	0.9900	C17—C18	1.390 (5)
C3—H3B	0.9900	C18—C19	1.387 (6)
C3—C4	1.523 (5)	C18—C22	1.511 (5)
C4—H4A	0.9900	C19—H19	0.9500
C4—H4B	0.9900	C19—C20	1.391 (5)
C4—C5	1.516 (5)	C20—C23	1.511 (5)
C5—H5A	0.9900	C21—H21A	0.9800
C5—H5B	0.9900	C21—H21B	0.9800
C6—C7	1.393 (5)	C21—H21C	0.9800
C6—C11	1.396 (5)	C22—H22A	0.9800
C7—C8	1.393 (5)	C22—H22B	0.9800
C7—C12	1.511 (5)	C22—H22C	0.9800
C8—H8	0.9500	C23—H23A	0.9800
C8—C9	1.399 (5)	C23—H23B	0.9800
C9—C10	1.389 (5)	C23—H23C	0.9800
C9—C13	1.506 (5)	C24—C25	1.383 (5)
C10—H10	0.9500	C24—C27	1.388 (4)
C10—C11	1.400 (5)	C25—C26	1.374 (4)
C11—C14	1.501 (5)
C1—N1—C2	127.4 (3)	C9—C13—H13C	109.5
C1—N1—C6	120.5 (3)	H13A—C13—H13B	109.5
C6—N1—C2	112.0 (3)	H13A—C13—H13C	109.5
C1—N2—C5	122.0 (3)	H13B—C13—H13C	109.5
C1—N2—C15	120.1 (3)	C11—C14—H14A	109.5
C15—N2—C5	116.7 (3)	C11—C14—H14B	109.5
N1—C1—Se1	119.6 (3)	C11—C14—H14C	109.5
N2—C1—Se1	120.9 (3)	H14A—C14—H14B	109.5
N2—C1—N1	119.5 (3)	H14A—C14—H14C	109.5
N1—C2—H2A	108.6	H14B—C14—H14C	109.5
N1—C2—H2B	108.6	C16—C15—N2	119.3 (3)
N1—C2—C3	114.5 (3)	C20—C15—N2	119.1 (3)
H2A—C2—H2B	107.6	C20—C15—C16	121.7 (3)
C3—C2—H2A	108.6	C15—C16—C21	121.0 (3)
C3—C2—H2B	108.6	C17—C16—C15	118.0 (3)
C2—C3—H3A	109.1	C17—C16—C21	120.9 (3)
C2—C3—H3B	109.1	C16—C17—H17	119.1
C2—C3—C4	112.4 (3)	C18—C17—C16	121.7 (3)
H3A—C3—H3B	107.9	C18—C17—H17	119.1
C4—C3—H3A	109.1	C17—C18—C22	120.3 (4)
C4—C3—H3B	109.1	C19—C18—C17	118.5 (3)
C3—C4—H4A	109.6	C19—C18—C22	121.2 (4)
C3—C4—H4B	109.6	C18—C19—H19	118.9
H4A—C4—H4B	108.1	C18—C19—C20	122.3 (4)
C5—C4—C3	110.1 (3)	C20—C19—H19	118.9
C5—C4—H4A	109.6	C15—C20—C23	121.7 (3)
C5—C4—H4B	109.6	C19—C20—C15	117.7 (3)
N2—C5—C4	112.3 (3)	C19—C20—C23	120.5 (3)
N2—C5—H5A	109.1	C16—C21—H21A	109.5
N2—C5—H5B	109.1	C16—C21—H21B	109.5
C4—C5—H5A	109.1	C16—C21—H21C	109.5
C4—C5—H5B	109.1	H21A—C21—H21B	109.5
H5A—C5—H5B	107.9	H21A—C21—H21C	109.5
C7—C6—N1	119.2 (3)	H21B—C21—H21C	109.5
C7—C6—C11	122.2 (3)	C18—C22—H22A	109.5
C11—C6—N1	118.4 (3)	C18—C22—H22B	109.5
C6—C7—C12	121.3 (3)	C18—C22—H22C	109.5
C8—C7—C6	118.1 (3)	H22A—C22—H22B	109.5
C8—C7—C12	120.5 (3)	H22A—C22—H22C	109.5
C7—C8—H8	119.2	H22B—C22—H22C	109.5
C7—C8—C9	121.6 (3)	C20—C23—H23A	109.5
C9—C8—H8	119.2	C20—C23—H23B	109.5
C8—C9—C13	120.5 (3)	C20—C23—H23C	109.5
C10—C9—C8	118.5 (3)	H23A—C23—H23B	109.5
C10—C9—C13	121.0 (3)	H23A—C23—H23C	109.5
C9—C10—H10	119.1	H23B—C23—H23C	109.5
C9—C10—C11	121.8 (3)	C25—C24—I1	119.6 (3)
C11—C10—H10	119.1	C25—C24—C27	117.3 (3)
C6—C11—C10	117.8 (3)	C27—C24—I1	123.1 (3)
C6—C11—C14	121.2 (3)	F1—C25—C24	120.6 (3)
C10—C11—C14	121.0 (3)	F1—C25—C26	117.9 (3)
C7—C12—H12A	109.5	C26—C25—C24	121.5 (3)
C7—C12—H12B	109.5	F2—C26—C25^i	120.2 (2)
C7—C12—H12C	109.5	F2—C26—C25	120.2 (2)
H12A—C12—H12B	109.5	C25—C26—C25^i	119.6 (5)
H12A—C12—H12C	109.5	F3—C27—C24	118.6 (2)
H12B—C12—H12C	109.5	F3—C27—C24^i	118.6 (2)
C9—C13—H13A	109.5	C24^i—C27—C24	122.8 (5)
C9—C13—H13B	109.5
I1—C24—C25—F1	0.7 (5)	C6—C7—C8—C9	0.1 (5)
I1—C24—C25—C26	−178.2 (2)	C7—C6—C11—C10	−1.3 (5)
I1—C24—C27—F3	−1.7 (3)	C7—C6—C11—C14	180.0 (3)
I1—C24—C27—C24^i	178.3 (3)	C7—C8—C9—C10	−0.8 (5)
F1—C25—C26—F2	0.9 (3)	C7—C8—C9—C13	−179.2 (3)
F1—C25—C26—C25^i	−179.1 (3)	C8—C9—C10—C11	0.4 (5)
N1—C2—C3—C4	80.2 (4)	C9—C10—C11—C6	0.6 (5)
N1—C6—C7—C8	−172.8 (3)	C9—C10—C11—C14	179.3 (3)
N1—C6—C7—C12	7.2 (5)	C11—C6—C7—C8	1.0 (5)
N1—C6—C11—C10	172.5 (3)	C11—C6—C7—C12	−179.0 (3)
N1—C6—C11—C14	−6.3 (5)	C12—C7—C8—C9	−179.9 (3)
N2—C15—C16—C17	178.4 (3)	C13—C9—C10—C11	178.9 (3)
N2—C15—C16—C21	1.4 (5)	C15—N2—C1—Se1	−6.9 (4)
N2—C15—C20—C19	−177.6 (3)	C15—N2—C1—N1	172.1 (3)
N2—C15—C20—C23	−0.6 (5)	C15—N2—C5—C4	−107.3 (4)
C1—N1—C2—C3	−25.2 (5)	C15—C16—C17—C18	−0.4 (5)
C1—N1—C6—C7	−89.9 (4)	C16—C15—C20—C19	3.0 (5)
C1—N1—C6—C11	96.1 (4)	C16—C15—C20—C23	180.0 (3)
C1—N2—C5—C4	85.4 (4)	C16—C17—C18—C19	2.1 (6)
C1—N2—C15—C16	−81.1 (4)	C16—C17—C18—C22	−177.2 (4)
C1—N2—C15—C20	99.5 (4)	C17—C18—C19—C20	−1.2 (6)
C2—N1—C1—Se1	159.8 (3)	C18—C19—C20—C15	−1.2 (5)
C2—N1—C1—N2	−19.1 (5)	C18—C19—C20—C23	−178.3 (4)
C2—N1—C6—C7	94.8 (4)	C20—C15—C16—C17	−2.2 (5)
C2—N1—C6—C11	−79.2 (4)	C20—C15—C16—C21	−179.2 (3)
C2—C3—C4—C5	−37.9 (4)	C21—C16—C17—C18	176.6 (3)
C3—C4—C5—N2	−48.3 (4)	C22—C18—C19—C20	178.0 (4)
C5—N2—C1—Se1	159.9 (3)	C24—C25—C26—F2	179.8 (2)
C5—N2—C1—N1	−21.1 (5)	C24—C25—C26—C25^i	−0.2 (2)
C5—N2—C15—C16	111.4 (4)	C25—C24—C27—F3	179.8 (2)
C5—N2—C15—C20	−68.0 (4)	C25—C24—C27—C24^i	−0.2 (2)
C6—N1—C1—Se1	−14.7 (4)	C27—C24—C25—F1	179.2 (3)
C6—N1—C1—N2	166.3 (3)	C27—C24—C25—C26	0.3 (5)
C6—N1—C2—C3	149.8 (3)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···Se1^ii	0.99	2.93	3.850 (4)	155
C5—H5A···I1^iii	0.99	3.30	4.150 (4)	145

Symmetry codes: (ii) x, y, z+1; (iii) −x+1, −y+1, −z+1.

(2SDiazMesS_14F4DIB_t)

Crystal data

C6F4I2·2(C23H30N2S)	Z = 1
Mr = 1134.96	F(000) = 574
Triclinic, P1	Dx = 1.540 Mg m^−3
a = 7.5020 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.2475 (11) Å	Cell parameters from 9951 reflections
c = 14.4780 (13) Å	θ = 2.6–27.5°
α = 104.905 (3)°	µ = 1.43 mm^−1
β = 95.822 (3)°	T = 100 K
γ = 104.609 (3)°	Needle, colourless
V = 1224.10 (19) Å^3	0.18 × 0.04 × 0.04 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	4439 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.045
φ and ω scans	θmax = 26.5°, θmin = 2.6°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −9→9
Tmin = 0.679, Tmax = 0.746	k = −15→15
16839 measured reflections	l = −18→18
5058 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.060	H-atom parameters constrained
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0038P)^2 + 1.3971P] where P = (Fo^2 + 2Fc^2)/3
5058 reflections	(Δ/σ)max = 0.001
295 parameters	Δρmax = 1.15 e Å^−3
0 restraints	Δρmin = −0.66 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.29580 (3)	0.27677 (2)	0.14236 (2)	0.01556 (6)
S1	0.55504 (10)	0.53960 (6)	0.26246 (5)	0.01568 (15)
F1	0.0727 (3)	0.04489 (15)	0.19582 (12)	0.0235 (4)
F2	−0.1456 (3)	−0.16580 (14)	0.08692 (12)	0.0245 (4)
N1	0.8921 (3)	0.5270 (2)	0.22468 (17)	0.0138 (5)
N2	0.8872 (3)	0.6583 (2)	0.37209 (17)	0.0133 (5)
C1	0.7930 (4)	0.5771 (2)	0.2875 (2)	0.0120 (6)
C2	1.0933 (4)	0.5744 (3)	0.2184 (2)	0.0179 (6)
H2A	1.106111	0.554089	0.149169	0.022*
H2B	1.167640	0.534230	0.251026	0.022*
C3	1.1767 (4)	0.7071 (3)	0.2633 (2)	0.0204 (7)
H3A	1.085365	0.747347	0.245208	0.024*
H3B	1.290447	0.734274	0.236499	0.024*
C4	1.2272 (4)	0.7418 (3)	0.3735 (2)	0.0208 (7)
H4A	1.350934	0.731298	0.392446	0.025*
H4B	1.235006	0.826010	0.401512	0.025*
C5	1.0799 (4)	0.6657 (3)	0.4127 (2)	0.0169 (6)
H5A	1.094365	0.585206	0.397572	0.020*
H5B	1.100732	0.698418	0.484231	0.020*
C6	0.8010 (4)	0.4195 (2)	0.1462 (2)	0.0138 (6)
C7	0.7930 (4)	0.3110 (2)	0.1625 (2)	0.0146 (6)
C8	0.7255 (4)	0.2095 (2)	0.0829 (2)	0.0171 (6)
H8	0.723016	0.135087	0.091961	0.021*
C9	0.6619 (4)	0.2146 (3)	−0.0089 (2)	0.0184 (6)
C10	0.6674 (4)	0.3244 (3)	−0.0212 (2)	0.0165 (6)
H10	0.620900	0.328536	−0.083336	0.020*
C11	0.7389 (4)	0.4281 (2)	0.0547 (2)	0.0139 (6)
C12	0.8531 (5)	0.3028 (3)	0.2622 (2)	0.0218 (7)
H12A	0.982807	0.351689	0.287466	0.033*
H12B	0.844002	0.220555	0.258550	0.033*
H12C	0.771540	0.330994	0.305594	0.033*
C13	0.5863 (5)	0.1035 (3)	−0.0939 (2)	0.0260 (7)
H13A	0.461354	0.099986	−0.124286	0.039*
H13B	0.578557	0.034244	−0.070789	0.039*
H13C	0.670119	0.104538	−0.141558	0.039*
C14	0.7517 (5)	0.5464 (2)	0.0383 (2)	0.0194 (7)
H14A	0.882016	0.586181	0.037278	0.029*
H14B	0.707619	0.594974	0.090936	0.029*
H14C	0.673610	0.534884	−0.023908	0.029*
C15	0.7896 (4)	0.7237 (2)	0.43748 (19)	0.0126 (6)
C16	0.7724 (4)	0.8319 (2)	0.4301 (2)	0.0167 (6)
C17	0.6925 (4)	0.8952 (2)	0.4991 (2)	0.0175 (6)
H17	0.681130	0.969506	0.495263	0.021*
C18	0.6281 (4)	0.8534 (3)	0.5741 (2)	0.0181 (6)
C19	0.6452 (4)	0.7440 (3)	0.5784 (2)	0.0195 (7)
H19	0.599896	0.713594	0.628348	0.023*
C20	0.7269 (4)	0.6785 (2)	0.5115 (2)	0.0151 (6)
C21	0.8361 (5)	0.8785 (3)	0.3478 (2)	0.0221 (7)
H21A	0.797936	0.949784	0.349510	0.033*
H21B	0.778781	0.818280	0.285557	0.033*
H21C	0.972698	0.897628	0.355114	0.033*
C22	0.5350 (5)	0.9215 (3)	0.6469 (2)	0.0267 (8)
H22A	0.400932	0.900551	0.621212	0.040*
H22B	0.591346	1.006335	0.658688	0.040*
H22C	0.552324	0.901668	0.707950	0.040*
C23	0.7425 (5)	0.5593 (3)	0.5171 (2)	0.0203 (7)
H23A	0.682094	0.539232	0.569934	0.030*
H23B	0.874821	0.562452	0.529624	0.030*
H23C	0.680589	0.499071	0.455502	0.030*
C24	0.1172 (4)	0.1118 (2)	0.0576 (2)	0.0139 (6)
C25	0.0390 (4)	0.0245 (2)	0.0987 (2)	0.0158 (6)
C26	−0.0752 (4)	−0.0844 (2)	0.0421 (2)	0.0160 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01416 (10)	0.01373 (9)	0.01738 (10)	0.00275 (7)	0.00281 (7)	0.00343 (7)
S1	0.0099 (4)	0.0168 (3)	0.0161 (4)	0.0026 (3)	0.0012 (3)	−0.0008 (3)
F1	0.0312 (11)	0.0208 (9)	0.0139 (9)	0.0003 (8)	0.0004 (8)	0.0060 (8)
F2	0.0314 (11)	0.0180 (9)	0.0217 (9)	−0.0013 (8)	0.0041 (8)	0.0105 (8)
N1	0.0105 (13)	0.0132 (11)	0.0159 (12)	0.0030 (10)	0.0031 (10)	0.0012 (10)
N2	0.0119 (13)	0.0133 (11)	0.0142 (12)	0.0042 (10)	0.0018 (10)	0.0030 (10)
C1	0.0118 (15)	0.0095 (13)	0.0134 (14)	0.0015 (11)	0.0001 (11)	0.0035 (11)
C2	0.0103 (15)	0.0184 (15)	0.0210 (16)	0.0035 (12)	0.0038 (12)	−0.0009 (13)
C3	0.0136 (16)	0.0183 (15)	0.0246 (17)	−0.0006 (13)	0.0066 (13)	0.0023 (14)
C4	0.0140 (16)	0.0187 (15)	0.0237 (17)	0.0009 (13)	0.0016 (13)	0.0003 (14)
C5	0.0113 (15)	0.0195 (15)	0.0187 (15)	0.0056 (12)	−0.0007 (12)	0.0038 (13)
C6	0.0105 (15)	0.0122 (13)	0.0164 (14)	0.0033 (12)	0.0057 (12)	−0.0012 (12)
C7	0.0094 (15)	0.0166 (14)	0.0190 (15)	0.0055 (12)	0.0046 (12)	0.0048 (12)
C8	0.0141 (16)	0.0112 (13)	0.0258 (16)	0.0046 (12)	0.0064 (13)	0.0032 (13)
C9	0.0118 (16)	0.0174 (15)	0.0219 (16)	0.0031 (12)	0.0052 (13)	−0.0011 (13)
C10	0.0152 (16)	0.0208 (15)	0.0140 (14)	0.0070 (13)	0.0057 (12)	0.0031 (12)
C11	0.0102 (15)	0.0143 (14)	0.0177 (15)	0.0035 (12)	0.0050 (12)	0.0045 (12)
C12	0.0244 (18)	0.0218 (16)	0.0235 (17)	0.0096 (14)	0.0066 (14)	0.0100 (14)
C13	0.0266 (19)	0.0195 (16)	0.0264 (18)	0.0061 (14)	0.0052 (15)	−0.0022 (14)
C14	0.0242 (18)	0.0176 (15)	0.0197 (16)	0.0076 (13)	0.0075 (13)	0.0079 (13)
C15	0.0111 (15)	0.0125 (13)	0.0105 (13)	0.0030 (11)	−0.0008 (11)	−0.0015 (11)
C16	0.0142 (16)	0.0139 (14)	0.0182 (15)	0.0009 (12)	0.0016 (12)	0.0020 (12)
C17	0.0172 (16)	0.0117 (13)	0.0201 (15)	0.0038 (12)	−0.0009 (13)	0.0008 (12)
C18	0.0183 (17)	0.0182 (15)	0.0134 (14)	0.0056 (13)	0.0004 (12)	−0.0025 (12)
C19	0.0225 (18)	0.0227 (16)	0.0134 (14)	0.0078 (14)	0.0026 (13)	0.0046 (13)
C20	0.0161 (16)	0.0156 (14)	0.0136 (14)	0.0064 (12)	−0.0005 (12)	0.0037 (12)
C21	0.0246 (18)	0.0174 (15)	0.0294 (18)	0.0094 (14)	0.0102 (15)	0.0103 (14)
C22	0.037 (2)	0.0284 (17)	0.0194 (16)	0.0181 (16)	0.0088 (15)	0.0046 (14)
C23	0.0243 (18)	0.0210 (15)	0.0205 (16)	0.0101 (14)	0.0059 (14)	0.0101 (13)
C24	0.0093 (14)	0.0118 (13)	0.0206 (15)	0.0041 (11)	0.0021 (12)	0.0038 (12)
C25	0.0160 (16)	0.0183 (14)	0.0120 (14)	0.0049 (13)	0.0007 (12)	0.0033 (12)
C26	0.0141 (16)	0.0163 (14)	0.0201 (15)	0.0037 (12)	0.0042 (12)	0.0100 (13)

Geometric parameters (Å, º)

I1—C24	2.100 (3)	C12—H12A	0.9800
S1—C1	1.703 (3)	C12—H12B	0.9800
F1—C25	1.348 (3)	C12—H12C	0.9800
F2—C26	1.353 (3)	C13—H13A	0.9800
N1—C1	1.355 (3)	C13—H13B	0.9800
N1—C2	1.496 (4)	C13—H13C	0.9800
N1—C6	1.453 (4)	C14—H14A	0.9800
N2—C1	1.353 (4)	C14—H14B	0.9800
N2—C5	1.476 (4)	C14—H14C	0.9800
N2—C15	1.455 (3)	C15—C16	1.394 (4)
C2—H2A	0.9900	C15—C20	1.397 (4)
C2—H2B	0.9900	C16—C17	1.385 (4)
C2—C3	1.522 (4)	C16—C21	1.517 (4)
C3—H3A	0.9900	C17—H17	0.9500
C3—H3B	0.9900	C17—C18	1.393 (4)
C3—C4	1.523 (4)	C18—C19	1.394 (4)
C4—H4A	0.9900	C18—C22	1.511 (4)
C4—H4B	0.9900	C19—H19	0.9500
C4—C5	1.513 (4)	C19—C20	1.388 (4)
C5—H5A	0.9900	C20—C23	1.515 (4)
C5—H5B	0.9900	C21—H21A	0.9800
C6—C7	1.397 (4)	C21—H21B	0.9800
C6—C11	1.397 (4)	C21—H21C	0.9800
C7—C8	1.398 (4)	C22—H22A	0.9800
C7—C12	1.504 (4)	C22—H22B	0.9800
C8—H8	0.9500	C22—H22C	0.9800
C8—C9	1.388 (4)	C23—H23A	0.9800
C9—C10	1.393 (4)	C23—H23B	0.9800
C9—C13	1.515 (4)	C23—H23C	0.9800
C10—H10	0.9500	C24—C25	1.387 (4)
C10—C11	1.388 (4)	C24—C26^i	1.378 (4)
C11—C14	1.509 (4)	C25—C26	1.379 (4)
C1—N1—C2	127.7 (2)	C9—C13—H13A	109.5
C1—N1—C6	120.8 (2)	C9—C13—H13B	109.5
C6—N1—C2	111.2 (2)	C9—C13—H13C	109.5
C1—N2—C5	121.8 (2)	H13A—C13—H13B	109.5
C1—N2—C15	120.8 (2)	H13A—C13—H13C	109.5
C15—N2—C5	116.0 (2)	H13B—C13—H13C	109.5
N1—C1—S1	121.6 (2)	C11—C14—H14A	109.5
N2—C1—S1	119.9 (2)	C11—C14—H14B	109.5
N2—C1—N1	118.6 (3)	C11—C14—H14C	109.5
N1—C2—H2A	108.5	H14A—C14—H14B	109.5
N1—C2—H2B	108.5	H14A—C14—H14C	109.5
N1—C2—C3	115.1 (2)	H14B—C14—H14C	109.5
H2A—C2—H2B	107.5	C16—C15—N2	120.5 (2)
C3—C2—H2A	108.5	C16—C15—C20	121.6 (3)
C3—C2—H2B	108.5	C20—C15—N2	117.8 (2)
C2—C3—H3A	109.2	C15—C16—C21	121.1 (3)
C2—C3—H3B	109.2	C17—C16—C15	118.2 (3)
C2—C3—C4	112.2 (2)	C17—C16—C21	120.7 (3)
H3A—C3—H3B	107.9	C16—C17—H17	118.9
C4—C3—H3A	109.2	C16—C17—C18	122.1 (3)
C4—C3—H3B	109.2	C18—C17—H17	118.9
C3—C4—H4A	109.7	C17—C18—C19	118.1 (3)
C3—C4—H4B	109.7	C17—C18—C22	121.5 (3)
H4A—C4—H4B	108.2	C19—C18—C22	120.3 (3)
C5—C4—C3	109.6 (2)	C18—C19—H19	119.2
C5—C4—H4A	109.7	C20—C19—C18	121.7 (3)
C5—C4—H4B	109.7	C20—C19—H19	119.2
N2—C5—C4	113.0 (2)	C15—C20—C23	120.9 (3)
N2—C5—H5A	109.0	C19—C20—C15	118.3 (3)
N2—C5—H5B	109.0	C19—C20—C23	120.7 (3)
C4—C5—H5A	109.0	C16—C21—H21A	109.5
C4—C5—H5B	109.0	C16—C21—H21B	109.5
H5A—C5—H5B	107.8	C16—C21—H21C	109.5
C7—C6—N1	118.7 (3)	H21A—C21—H21B	109.5
C7—C6—C11	122.0 (3)	H21A—C21—H21C	109.5
C11—C6—N1	119.0 (2)	H21B—C21—H21C	109.5
C6—C7—C8	117.7 (3)	C18—C22—H22A	109.5
C6—C7—C12	121.3 (3)	C18—C22—H22B	109.5
C8—C7—C12	120.9 (3)	C18—C22—H22C	109.5
C7—C8—H8	119.1	H22A—C22—H22B	109.5
C9—C8—C7	121.8 (3)	H22A—C22—H22C	109.5
C9—C8—H8	119.1	H22B—C22—H22C	109.5
C8—C9—C10	118.4 (3)	C20—C23—H23A	109.5
C8—C9—C13	121.1 (3)	C20—C23—H23B	109.5
C10—C9—C13	120.4 (3)	C20—C23—H23C	109.5
C9—C10—H10	119.0	H23A—C23—H23B	109.5
C11—C10—C9	121.9 (3)	H23A—C23—H23C	109.5
C11—C10—H10	119.0	H23B—C23—H23C	109.5
C6—C11—C14	121.2 (3)	C25—C24—I1	121.8 (2)
C10—C11—C6	118.0 (3)	C26^i—C24—I1	121.3 (2)
C10—C11—C14	120.8 (3)	C26^i—C24—C25	116.8 (3)
C7—C12—H12A	109.5	F1—C25—C24	120.3 (3)
C7—C12—H12B	109.5	F1—C25—C26	118.5 (2)
C7—C12—H12C	109.5	C26—C25—C24	121.3 (3)
H12A—C12—H12B	109.5	F2—C26—C24^i	119.9 (3)
H12A—C12—H12C	109.5	F2—C26—C25	118.2 (3)
H12B—C12—H12C	109.5	C24^i—C26—C25	121.9 (3)
I1—C24—C25—F1	1.7 (4)	C6—C7—C8—C9	−2.2 (4)
I1—C24—C25—C26	−178.7 (2)	C7—C6—C11—C10	0.1 (4)
F1—C25—C26—F2	−0.8 (4)	C7—C6—C11—C14	−179.0 (3)
F1—C25—C26—C24^i	179.6 (3)	C7—C8—C9—C10	0.4 (4)
N1—C2—C3—C4	78.6 (3)	C7—C8—C9—C13	−179.0 (3)
N1—C6—C7—C8	−172.4 (2)	C8—C9—C10—C11	1.8 (4)
N1—C6—C7—C12	8.2 (4)	C9—C10—C11—C6	−2.0 (4)
N1—C6—C11—C10	174.4 (2)	C9—C10—C11—C14	177.1 (3)
N1—C6—C11—C14	−4.7 (4)	C11—C6—C7—C8	2.0 (4)
N2—C15—C16—C17	−174.6 (3)	C11—C6—C7—C12	−177.5 (3)
N2—C15—C16—C21	6.5 (4)	C12—C7—C8—C9	177.2 (3)
N2—C15—C20—C19	175.6 (3)	C13—C9—C10—C11	−178.8 (3)
N2—C15—C20—C23	−6.1 (4)	C15—N2—C1—S1	−6.8 (3)
C1—N1—C2—C3	−21.4 (4)	C15—N2—C1—N1	173.6 (2)
C1—N1—C6—C7	−91.3 (3)	C15—N2—C5—C4	−106.9 (3)
C1—N1—C6—C11	94.2 (3)	C15—C16—C17—C18	−0.6 (5)
C1—N2—C5—C4	86.5 (3)	C16—C15—C20—C19	0.3 (5)
C1—N2—C15—C16	−91.5 (3)	C16—C15—C20—C23	178.5 (3)
C1—N2—C15—C20	93.1 (3)	C16—C17—C18—C19	−0.2 (5)
C2—N1—C1—S1	158.3 (2)	C16—C17—C18—C22	−177.8 (3)
C2—N1—C1—N2	−22.0 (4)	C17—C18—C19—C20	1.2 (5)
C2—N1—C6—C7	93.7 (3)	C18—C19—C20—C15	−1.2 (5)
C2—N1—C6—C11	−80.8 (3)	C18—C19—C20—C23	−179.5 (3)
C2—C3—C4—C5	−38.3 (3)	C20—C15—C16—C17	0.6 (4)
C3—C4—C5—N2	−48.2 (3)	C20—C15—C16—C21	−178.3 (3)
C5—N2—C1—S1	159.2 (2)	C21—C16—C17—C18	178.3 (3)
C5—N2—C1—N1	−20.5 (4)	C22—C18—C19—C20	178.8 (3)
C5—N2—C15—C16	101.8 (3)	C24—C25—C26—F2	179.5 (3)
C5—N2—C15—C20	−73.6 (3)	C24—C25—C26—C24^i	−0.1 (5)
C6—N1—C1—S1	−15.8 (4)	C26^i—C24—C25—F1	−179.6 (3)
C6—N1—C1—N2	163.9 (2)	C26^i—C24—C25—C26	0.1 (5)
C6—N1—C2—C3	153.2 (2)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···S1^ii	0.99	2.88	3.609 (3)	131

Symmetry code: (ii) x+1, y, z.

(2SDiazMesSe_14F4DIB_t)

Crystal data

C6F4I2·2(C23H30N2Se)	Z = 1
Mr = 1228.76	F(000) = 610
Triclinic, P1	Dx = 1.649 Mg m^−3
a = 7.5969 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.1995 (7) Å	Cell parameters from 9854 reflections
c = 14.4439 (8) Å	θ = 2.6–30.1°
α = 104.6128 (18)°	µ = 2.80 mm^−1
β = 95.7464 (19)°	T = 100 K
γ = 104.1188 (18)°	Block, yellow
V = 1237.42 (12) Å^3	0.21 × 0.17 × 0.10 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	6861 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.031
φ and ω scans	θmax = 30.1°, θmin = 2.6°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −10→10
Tmin = 0.582, Tmax = 0.746	k = −17→17
42081 measured reflections	l = −20→20
7215 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.017	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.041	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0149P)^2 + 0.707P] where P = (Fo^2 + 2Fc^2)/3
7215 reflections	(Δ/σ)max = 0.002
295 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.51 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.29421 (2)	0.27454 (2)	0.14125 (2)	0.01328 (3)
F1	0.07210 (13)	0.04340 (8)	0.19578 (6)	0.02354 (18)
F2	−0.14634 (13)	−0.16474 (7)	0.08787 (6)	0.02381 (18)
C24	0.11713 (17)	0.11065 (11)	0.05762 (9)	0.0135 (2)
C25	0.03840 (18)	0.02384 (12)	0.09870 (9)	0.0155 (2)
C26	−0.07587 (18)	−0.08429 (11)	0.04264 (10)	0.0156 (2)
Se1	0.53807 (2)	0.54118 (2)	0.26159 (2)	0.01269 (3)
N1	0.89086 (14)	0.52948 (9)	0.22430 (8)	0.01150 (19)
N2	0.88545 (14)	0.66002 (9)	0.37245 (7)	0.01112 (18)
C1	0.79458 (16)	0.57953 (10)	0.28797 (9)	0.0105 (2)
C2	1.08818 (17)	0.57688 (11)	0.21712 (10)	0.0160 (2)
H2A	1.100601	0.556192	0.147730	0.019*
H2B	1.162774	0.537077	0.250065	0.019*
C3	1.16776 (18)	0.70958 (12)	0.26068 (10)	0.0178 (2)
H3A	1.076344	0.749388	0.242428	0.021*
H3B	1.279035	0.736640	0.233096	0.021*
C4	1.21868 (18)	0.74533 (12)	0.37126 (10)	0.0193 (3)
H4A	1.342248	0.736341	0.389889	0.023*
H4B	1.222933	0.829170	0.398429	0.023*
C5	1.07739 (17)	0.66845 (12)	0.41228 (10)	0.0157 (2)
H5A	1.094303	0.588277	0.397438	0.019*
H5B	1.098668	0.701314	0.483803	0.019*
C6	0.80139 (16)	0.42211 (10)	0.14695 (9)	0.0115 (2)
C7	0.79565 (17)	0.31380 (11)	0.16436 (9)	0.0131 (2)
C8	0.72764 (18)	0.21152 (11)	0.08614 (10)	0.0157 (2)
H8	0.724884	0.137230	0.096353	0.019*
C9	0.66397 (18)	0.21586 (11)	−0.00619 (10)	0.0161 (2)
C10	0.66887 (17)	0.32562 (12)	−0.02003 (9)	0.0153 (2)
H10	0.622203	0.329230	−0.082387	0.018*
C11	0.74027 (17)	0.43005 (11)	0.05498 (9)	0.0128 (2)
C12	0.8565 (2)	0.30633 (12)	0.26441 (10)	0.0192 (3)
H12A	0.984150	0.354744	0.288649	0.029*
H12B	0.848245	0.224099	0.261610	0.029*
H12C	0.776634	0.335292	0.308149	0.029*
C13	0.5884 (2)	0.10455 (13)	−0.08971 (11)	0.0238 (3)
H13A	0.464073	0.100877	−0.118693	0.036*
H13B	0.583617	0.035681	−0.065800	0.036*
H13C	0.668591	0.104900	−0.138797	0.036*
C14	0.75084 (19)	0.54699 (12)	0.03652 (10)	0.0175 (2)
H14A	0.878419	0.585639	0.033389	0.026*
H14B	0.709294	0.596936	0.089342	0.026*
H14C	0.671700	0.534734	−0.025209	0.026*
C15	0.78945 (16)	0.72421 (11)	0.43822 (9)	0.0117 (2)
C16	0.77107 (17)	0.83305 (11)	0.43069 (9)	0.0134 (2)
C17	0.68792 (18)	0.89529 (11)	0.50018 (10)	0.0159 (2)
H17	0.674339	0.969484	0.496380	0.019*
C18	0.62445 (19)	0.85183 (12)	0.57476 (9)	0.0171 (2)
C19	0.64414 (19)	0.74265 (12)	0.57928 (9)	0.0171 (2)
H19	0.600336	0.711780	0.629448	0.021*
C20	0.72654 (17)	0.67766 (11)	0.51200 (9)	0.0138 (2)
C21	0.8319 (2)	0.88106 (13)	0.34914 (11)	0.0209 (3)
H21A	0.795970	0.953721	0.352749	0.031*
H21B	0.773122	0.822562	0.286736	0.031*
H21C	0.966066	0.898118	0.354880	0.031*
C22	0.5320 (2)	0.91916 (14)	0.64792 (11)	0.0254 (3)
H22A	0.398836	0.894762	0.624485	0.038*
H22B	0.580794	1.003915	0.656638	0.038*
H22C	0.556357	0.902516	0.710146	0.038*
C23	0.7435 (2)	0.55879 (12)	0.51707 (10)	0.0186 (3)
H23A	0.683716	0.537804	0.569698	0.028*
H23B	0.874099	0.561874	0.529548	0.028*
H23C	0.683821	0.499336	0.455269	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01209 (4)	0.01205 (4)	0.01442 (4)	0.00209 (3)	0.00187 (3)	0.00294 (3)
F1	0.0322 (5)	0.0206 (4)	0.0124 (4)	−0.0011 (3)	0.0000 (3)	0.0048 (3)
F2	0.0326 (5)	0.0163 (4)	0.0192 (4)	−0.0029 (3)	0.0035 (3)	0.0090 (3)
C24	0.0128 (5)	0.0108 (5)	0.0159 (6)	0.0027 (4)	0.0014 (4)	0.0030 (4)
C25	0.0180 (6)	0.0155 (6)	0.0121 (6)	0.0040 (5)	0.0015 (4)	0.0035 (5)
C26	0.0170 (6)	0.0129 (5)	0.0174 (6)	0.0023 (5)	0.0040 (5)	0.0069 (5)
Se1	0.00791 (5)	0.01396 (6)	0.01315 (6)	0.00251 (4)	0.00137 (4)	−0.00079 (4)
N1	0.0086 (4)	0.0109 (4)	0.0123 (5)	0.0012 (4)	0.0020 (4)	−0.0001 (4)
N2	0.0100 (4)	0.0118 (5)	0.0105 (5)	0.0039 (4)	0.0006 (3)	0.0009 (4)
C1	0.0096 (5)	0.0094 (5)	0.0122 (5)	0.0026 (4)	0.0016 (4)	0.0029 (4)
C2	0.0096 (5)	0.0154 (6)	0.0194 (6)	0.0012 (4)	0.0053 (4)	−0.0003 (5)
C3	0.0136 (6)	0.0147 (6)	0.0211 (6)	−0.0005 (5)	0.0065 (5)	0.0013 (5)
C4	0.0117 (5)	0.0180 (6)	0.0215 (6)	−0.0002 (5)	0.0019 (5)	−0.0016 (5)
C5	0.0113 (5)	0.0184 (6)	0.0151 (6)	0.0043 (5)	−0.0017 (4)	0.0020 (5)
C6	0.0100 (5)	0.0101 (5)	0.0124 (5)	0.0024 (4)	0.0030 (4)	−0.0004 (4)
C7	0.0113 (5)	0.0132 (5)	0.0151 (6)	0.0041 (4)	0.0029 (4)	0.0035 (4)
C8	0.0144 (6)	0.0102 (5)	0.0217 (6)	0.0038 (4)	0.0045 (5)	0.0021 (5)
C9	0.0140 (5)	0.0134 (6)	0.0170 (6)	0.0028 (4)	0.0041 (5)	−0.0023 (5)
C10	0.0144 (6)	0.0168 (6)	0.0125 (5)	0.0031 (5)	0.0037 (4)	0.0012 (5)
C11	0.0118 (5)	0.0123 (5)	0.0142 (6)	0.0034 (4)	0.0046 (4)	0.0029 (4)
C12	0.0222 (6)	0.0186 (6)	0.0182 (6)	0.0075 (5)	0.0021 (5)	0.0066 (5)
C13	0.0253 (7)	0.0161 (6)	0.0222 (7)	0.0037 (5)	0.0013 (5)	−0.0054 (5)
C14	0.0228 (6)	0.0145 (6)	0.0167 (6)	0.0052 (5)	0.0052 (5)	0.0062 (5)
C15	0.0115 (5)	0.0116 (5)	0.0101 (5)	0.0035 (4)	0.0006 (4)	0.0001 (4)
C16	0.0134 (5)	0.0111 (5)	0.0137 (5)	0.0025 (4)	0.0016 (4)	0.0013 (4)
C17	0.0168 (6)	0.0115 (5)	0.0168 (6)	0.0045 (4)	0.0012 (5)	−0.0004 (5)
C18	0.0178 (6)	0.0188 (6)	0.0126 (6)	0.0073 (5)	0.0017 (5)	−0.0010 (5)
C19	0.0195 (6)	0.0216 (6)	0.0114 (5)	0.0081 (5)	0.0037 (5)	0.0042 (5)
C20	0.0153 (5)	0.0146 (5)	0.0115 (5)	0.0054 (4)	0.0008 (4)	0.0029 (4)
C21	0.0267 (7)	0.0172 (6)	0.0248 (7)	0.0101 (5)	0.0110 (6)	0.0103 (5)
C22	0.0331 (8)	0.0257 (7)	0.0193 (7)	0.0154 (6)	0.0094 (6)	0.0011 (6)
C23	0.0240 (7)	0.0185 (6)	0.0186 (6)	0.0101 (5)	0.0068 (5)	0.0095 (5)

Geometric parameters (Å, º)

I1—C24	2.1000 (12)	C10—H10	0.9500
F1—C25	1.3485 (15)	C10—C11	1.3928 (17)
F2—C26	1.3468 (15)	C11—C14	1.5009 (18)
C24—C25	1.3823 (18)	C12—H12A	0.9800
C24—C26^i	1.3870 (18)	C12—H12B	0.9800
C25—C26	1.3824 (18)	C12—H12C	0.9800
Se1—C1	1.8650 (12)	C13—H13A	0.9800
N1—C1	1.3502 (15)	C13—H13B	0.9800
N1—C2	1.4935 (15)	C13—H13C	0.9800
N1—C6	1.4495 (15)	C14—H14A	0.9800
N2—C1	1.3511 (15)	C14—H14B	0.9800
N2—C5	1.4822 (15)	C14—H14C	0.9800
N2—C15	1.4455 (15)	C15—C16	1.3981 (17)
C2—H2A	0.9900	C15—C20	1.4006 (18)
C2—H2B	0.9900	C16—C17	1.3998 (17)
C2—C3	1.5214 (18)	C16—C21	1.5062 (19)
C3—H3A	0.9900	C17—H17	0.9500
C3—H3B	0.9900	C17—C18	1.3933 (19)
C3—C4	1.527 (2)	C18—C19	1.3928 (19)
C4—H4A	0.9900	C18—C22	1.5088 (19)
C4—H4B	0.9900	C19—H19	0.9500
C4—C5	1.5164 (19)	C19—C20	1.3929 (18)
C5—H5A	0.9900	C20—C23	1.5060 (18)
C5—H5B	0.9900	C21—H21A	0.9800
C6—C7	1.3975 (17)	C21—H21B	0.9800
C6—C11	1.3974 (17)	C21—H21C	0.9800
C7—C8	1.3992 (18)	C22—H22A	0.9800
C7—C12	1.5044 (18)	C22—H22B	0.9800
C8—H8	0.9500	C22—H22C	0.9800
C8—C9	1.3907 (19)	C23—H23A	0.9800
C9—C10	1.3952 (19)	C23—H23B	0.9800
C9—C13	1.5111 (18)	C23—H23C	0.9800
C25—C24—I1	122.28 (9)	C6—C11—C14	121.55 (11)
C25—C24—C26^i	116.85 (11)	C10—C11—C6	117.98 (12)
C26^i—C24—I1	120.86 (9)	C10—C11—C14	120.47 (12)
F1—C25—C24	120.10 (11)	C7—C12—H12A	109.5
F1—C25—C26	118.22 (12)	C7—C12—H12B	109.5
C24—C25—C26	121.67 (12)	C7—C12—H12C	109.5
F2—C26—C24^i	120.30 (11)	H12A—C12—H12B	109.5
F2—C26—C25	118.23 (12)	H12A—C12—H12C	109.5
C25—C26—C24^i	121.47 (12)	H12B—C12—H12C	109.5
C1—N1—C2	127.32 (10)	C9—C13—H13A	109.5
C1—N1—C6	120.93 (10)	C9—C13—H13B	109.5
C6—N1—C2	111.58 (9)	C9—C13—H13C	109.5
C1—N2—C5	121.65 (10)	H13A—C13—H13B	109.5
C1—N2—C15	121.29 (10)	H13A—C13—H13C	109.5
C15—N2—C5	115.77 (10)	H13B—C13—H13C	109.5
N1—C1—Se1	121.48 (9)	C11—C14—H14A	109.5
N1—C1—N2	119.53 (10)	C11—C14—H14B	109.5
N2—C1—Se1	118.99 (9)	C11—C14—H14C	109.5
N1—C2—H2A	108.5	H14A—C14—H14B	109.5
N1—C2—H2B	108.5	H14A—C14—H14C	109.5
N1—C2—C3	115.05 (10)	H14B—C14—H14C	109.5
H2A—C2—H2B	107.5	C16—C15—N2	119.98 (11)
C3—C2—H2A	108.5	C16—C15—C20	121.76 (11)
C3—C2—H2B	108.5	C20—C15—N2	118.16 (11)
C2—C3—H3A	109.1	C15—C16—C17	117.69 (12)
C2—C3—H3B	109.1	C15—C16—C21	121.83 (11)
C2—C3—C4	112.39 (12)	C17—C16—C21	120.45 (12)
H3A—C3—H3B	107.9	C16—C17—H17	119.0
C4—C3—H3A	109.1	C18—C17—C16	122.07 (12)
C4—C3—H3B	109.1	C18—C17—H17	119.0
C3—C4—H4A	109.7	C17—C18—C22	121.30 (13)
C3—C4—H4B	109.7	C19—C18—C17	118.46 (12)
H4A—C4—H4B	108.2	C19—C18—C22	120.22 (13)
C5—C4—C3	109.84 (11)	C18—C19—H19	119.2
C5—C4—H4A	109.7	C18—C19—C20	121.57 (12)
C5—C4—H4B	109.7	C20—C19—H19	119.2
N2—C5—C4	112.61 (11)	C15—C20—C23	120.76 (11)
N2—C5—H5A	109.1	C19—C20—C15	118.46 (12)
N2—C5—H5B	109.1	C19—C20—C23	120.76 (12)
C4—C5—H5A	109.1	C16—C21—H21A	109.5
C4—C5—H5B	109.1	C16—C21—H21B	109.5
H5A—C5—H5B	107.8	C16—C21—H21C	109.5
C7—C6—N1	118.59 (11)	H21A—C21—H21B	109.5
C7—C6—C11	121.95 (11)	H21A—C21—H21C	109.5
C11—C6—N1	119.15 (11)	H21B—C21—H21C	109.5
C6—C7—C8	117.99 (12)	C18—C22—H22A	109.5
C6—C7—C12	121.35 (11)	C18—C22—H22B	109.5
C8—C7—C12	120.64 (12)	C18—C22—H22C	109.5
C7—C8—H8	119.2	H22A—C22—H22B	109.5
C9—C8—C7	121.67 (12)	H22A—C22—H22C	109.5
C9—C8—H8	119.2	H22B—C22—H22C	109.5
C8—C9—C10	118.49 (12)	C20—C23—H23A	109.5
C8—C9—C13	121.11 (12)	C20—C23—H23B	109.5
C10—C9—C13	120.39 (13)	C20—C23—H23C	109.5
C9—C10—H10	119.1	H23A—C23—H23B	109.5
C11—C10—C9	121.86 (12)	H23A—C23—H23C	109.5
C11—C10—H10	119.1	H23B—C23—H23C	109.5
I1—C24—C25—F1	0.98 (17)	C5—N2—C15—C20	−75.08 (14)
I1—C24—C25—C26	−179.07 (10)	C6—N1—C1—Se1	−17.46 (16)
F1—C25—C26—F2	−0.52 (19)	C6—N1—C1—N2	163.12 (11)
F1—C25—C26—C24^i	179.85 (12)	C6—N1—C2—C3	152.96 (11)
C24—C25—C26—F2	179.52 (12)	C6—C7—C8—C9	−1.18 (19)
C24—C25—C26—C24^i	−0.1 (2)	C7—C6—C11—C10	1.21 (18)
C26^i—C24—C25—F1	−179.85 (12)	C7—C6—C11—C14	−178.64 (11)
C26^i—C24—C25—C26	0.1 (2)	C7—C8—C9—C10	−0.01 (19)
N1—C2—C3—C4	78.75 (15)	C7—C8—C9—C13	−179.14 (12)
N1—C6—C7—C8	−172.96 (11)	C8—C9—C10—C11	1.90 (19)
N1—C6—C7—C12	8.40 (17)	C9—C10—C11—C6	−2.48 (18)
N1—C6—C11—C10	174.70 (11)	C9—C10—C11—C14	177.38 (12)
N1—C6—C11—C14	−5.15 (17)	C11—C6—C7—C8	0.56 (18)
N2—C15—C16—C17	−175.78 (11)	C11—C6—C7—C12	−178.08 (12)
N2—C15—C16—C21	6.30 (19)	C12—C7—C8—C9	177.47 (12)
N2—C15—C20—C19	176.06 (11)	C13—C9—C10—C11	−178.96 (12)
N2—C15—C20—C23	−5.37 (18)	C15—N2—C1—Se1	−5.62 (15)
C1—N1—C2—C3	−22.31 (19)	C15—N2—C1—N1	173.81 (11)
C1—N1—C6—C7	−90.75 (14)	C15—N2—C5—C4	−107.11 (12)
C1—N1—C6—C11	95.54 (14)	C15—C16—C17—C18	−0.10 (19)
C1—N2—C5—C4	85.67 (14)	C16—C15—C20—C19	−0.15 (19)
C1—N2—C15—C16	−91.52 (15)	C16—C15—C20—C23	178.42 (12)
C1—N2—C15—C20	92.20 (14)	C16—C17—C18—C19	−0.4 (2)
C2—N1—C1—Se1	157.41 (10)	C16—C17—C18—C22	−178.86 (13)
C2—N1—C1—N2	−22.01 (19)	C17—C18—C19—C20	0.6 (2)
C2—N1—C6—C7	93.64 (13)	C18—C19—C20—C15	−0.3 (2)
C2—N1—C6—C11	−80.07 (14)	C18—C19—C20—C23	−178.91 (13)
C2—C3—C4—C5	−37.50 (15)	C20—C15—C16—C17	0.36 (18)
C3—C4—C5—N2	−48.67 (15)	C20—C15—C16—C21	−177.56 (12)
C5—N2—C1—Se1	160.90 (9)	C21—C16—C17—C18	177.85 (13)
C5—N2—C1—N1	−19.67 (17)	C22—C18—C19—C20	179.10 (13)
C5—N2—C15—C16	101.20 (13)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···Se1^ii	0.99	2.83	3.5653 (13)	132

Symmetry code: (ii) x+1, y, z.

(2SDiazMesS_14F4DIB_m)

Crystal data

C6F4I2·2(C23H30N2S)	F(000) = 1148
Mr = 1134.96	Dx = 1.514 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.3377 (6) Å	Cell parameters from 9688 reflections
b = 15.2129 (6) Å	θ = 3.0–27.5°
c = 13.0613 (5) Å	µ = 1.40 mm^−1
β = 109.998 (1)°	T = 100 K
V = 2490.41 (18) Å^3	Plank, colourless
Z = 2	0.18 × 0.16 × 0.06 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	5146 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.042
φ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −17→17
Tmin = 0.683, Tmax = 0.746	k = −19→19
53110 measured reflections	l = −16→16
5713 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.056	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0119P)^2 + 3.5016P] where P = (Fo^2 + 2Fc^2)/3
5713 reflections	(Δ/σ)max = 0.004
295 parameters	Δρmax = 1.26 e Å^−3
0 restraints	Δρmin = −1.41 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	1.13129 (2)	0.62340 (2)	0.73210 (2)	0.02337 (5)
S1	0.37912 (4)	0.79965 (3)	0.39037 (4)	0.01687 (10)
F2	1.20421 (9)	0.46075 (8)	0.62252 (10)	0.0246 (3)
C3	0.49185 (16)	0.57412 (13)	0.63523 (16)	0.0197 (4)
H3A	0.507766	0.571162	0.566630	0.024*
H3B	0.495107	0.513619	0.664116	0.024*
F1	0.89329 (10)	0.63241 (8)	0.55695 (11)	0.0277 (3)
C4	0.57620 (17)	0.63074 (13)	0.71771 (16)	0.0205 (4)
H4A	0.580688	0.614476	0.792545	0.025*
H4B	0.646794	0.620042	0.710729	0.025*
N2	0.51882 (13)	0.75272 (10)	0.58183 (12)	0.0147 (3)
N1	0.35196 (13)	0.68429 (10)	0.53150 (13)	0.0160 (3)
C7	0.17559 (16)	0.74841 (13)	0.49860 (15)	0.0175 (4)
C6	0.23958 (15)	0.68838 (12)	0.46805 (15)	0.0158 (4)
C5	0.54739 (16)	0.72763 (13)	0.69791 (15)	0.0181 (4)
H5A	0.486460	0.740690	0.722401	0.022*
H5B	0.608722	0.763662	0.742145	0.022*
C1	0.41943 (15)	0.74179 (12)	0.50860 (15)	0.0150 (4)
C9	0.02180 (17)	0.69461 (15)	0.35007 (16)	0.0231 (4)
C8	0.06698 (16)	0.75008 (14)	0.43857 (16)	0.0207 (4)
H8	0.022401	0.790268	0.458626	0.025*
C2	0.38031 (16)	0.61042 (13)	0.61133 (16)	0.0191 (4)
H2A	0.328331	0.562203	0.583017	0.023*
H2B	0.373286	0.630968	0.680481	0.023*
C10	0.08751 (18)	0.63467 (14)	0.32334 (16)	0.0231 (4)
H10	0.057102	0.595635	0.264016	0.028*
C11	0.19666 (17)	0.63011 (13)	0.38093 (16)	0.0195 (4)
C12	0.22371 (17)	0.81173 (13)	0.59116 (16)	0.0210 (4)
H12A	0.269204	0.853852	0.570764	0.031*
H12B	0.266613	0.779145	0.656085	0.031*
H12C	0.166598	0.843371	0.606828	0.031*
C13	−0.09471 (18)	0.70211 (18)	0.28121 (19)	0.0341 (5)
H13A	−0.103903	0.748966	0.227269	0.051*
H13B	−0.136456	0.715991	0.327978	0.051*
H13C	−0.119375	0.646242	0.243700	0.051*
C14	0.26688 (19)	0.56723 (14)	0.34765 (18)	0.0271 (5)
H14A	0.325501	0.599716	0.335980	0.041*
H14B	0.224842	0.537511	0.280017	0.041*
H14C	0.296064	0.523481	0.405261	0.041*
C15	0.59767 (15)	0.80265 (12)	0.55321 (15)	0.0150 (4)
C16	0.65956 (16)	0.76027 (12)	0.50068 (15)	0.0168 (4)
C17	0.74017 (16)	0.80762 (13)	0.48114 (16)	0.0189 (4)
H17	0.783238	0.779208	0.446315	0.023*
C18	0.75976 (16)	0.89553 (14)	0.51109 (17)	0.0209 (4)
C19	0.69446 (16)	0.93662 (13)	0.56040 (16)	0.0200 (4)
H19	0.705433	0.997049	0.579236	0.024*
C20	0.61359 (16)	0.89121 (12)	0.58269 (16)	0.0178 (4)
C21	0.63786 (17)	0.66612 (13)	0.46366 (17)	0.0201 (4)
H21A	0.681050	0.650551	0.418891	0.030*
H21B	0.562061	0.659194	0.420626	0.030*
H21C	0.656351	0.627415	0.527417	0.030*
C22	0.84933 (19)	0.94472 (16)	0.4908 (2)	0.0313 (5)
H22A	0.917182	0.915133	0.528783	0.047*
H22B	0.852020	1.005002	0.518111	0.047*
H22C	0.837020	0.946004	0.412458	0.047*
C23	0.54430 (18)	0.93782 (13)	0.63567 (18)	0.0235 (4)
H23A	0.565134	0.919970	0.712213	0.035*
H23B	0.469410	0.922293	0.597744	0.035*
H23C	0.553302	1.001505	0.631499	0.035*
C24	1.05153 (15)	0.54933 (12)	0.59479 (15)	0.0161 (4)
C25	0.94751 (16)	0.56681 (12)	0.53043 (16)	0.0178 (4)
C26	1.10289 (15)	0.48147 (13)	0.56245 (16)	0.0173 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.03121 (8)	0.01751 (7)	0.01614 (7)	−0.00103 (5)	0.00131 (5)	−0.00372 (5)
S1	0.0177 (2)	0.0179 (2)	0.0136 (2)	0.00158 (17)	0.00342 (17)	0.00464 (17)
F2	0.0141 (6)	0.0239 (6)	0.0296 (7)	0.0036 (5)	−0.0007 (5)	−0.0040 (5)
C3	0.0261 (11)	0.0149 (9)	0.0169 (9)	0.0017 (8)	0.0059 (8)	0.0033 (7)
F1	0.0232 (6)	0.0255 (6)	0.0316 (7)	0.0082 (5)	0.0057 (5)	−0.0114 (5)
C4	0.0237 (10)	0.0213 (10)	0.0131 (9)	0.0037 (8)	0.0019 (8)	0.0048 (7)
N2	0.0176 (8)	0.0145 (7)	0.0116 (7)	0.0012 (6)	0.0045 (6)	0.0010 (6)
N1	0.0186 (8)	0.0143 (7)	0.0142 (7)	0.0015 (6)	0.0044 (6)	0.0034 (6)
C7	0.0212 (10)	0.0167 (9)	0.0150 (9)	−0.0024 (7)	0.0068 (7)	0.0032 (7)
C6	0.0180 (9)	0.0153 (8)	0.0135 (8)	−0.0019 (7)	0.0047 (7)	0.0026 (7)
C5	0.0228 (10)	0.0200 (9)	0.0095 (8)	0.0008 (8)	0.0031 (7)	0.0005 (7)
C1	0.0194 (9)	0.0138 (8)	0.0125 (8)	0.0030 (7)	0.0064 (7)	−0.0007 (7)
C9	0.0194 (10)	0.0314 (11)	0.0173 (9)	−0.0074 (8)	0.0047 (8)	0.0057 (8)
C8	0.0202 (10)	0.0237 (10)	0.0196 (9)	0.0003 (8)	0.0088 (8)	0.0038 (8)
C2	0.0231 (10)	0.0168 (9)	0.0165 (9)	0.0005 (8)	0.0058 (8)	0.0051 (7)
C10	0.0282 (11)	0.0242 (10)	0.0147 (9)	−0.0102 (8)	0.0044 (8)	−0.0004 (8)
C11	0.0264 (11)	0.0155 (9)	0.0156 (9)	−0.0026 (8)	0.0060 (8)	0.0023 (7)
C12	0.0228 (10)	0.0196 (9)	0.0197 (10)	0.0027 (8)	0.0062 (8)	−0.0020 (8)
C13	0.0212 (11)	0.0514 (15)	0.0254 (11)	−0.0074 (10)	0.0022 (9)	0.0021 (11)
C14	0.0395 (13)	0.0193 (10)	0.0207 (10)	0.0029 (9)	0.0082 (9)	−0.0022 (8)
C15	0.0156 (9)	0.0167 (9)	0.0108 (8)	0.0009 (7)	0.0019 (7)	0.0010 (7)
C16	0.0189 (9)	0.0155 (9)	0.0136 (9)	0.0047 (7)	0.0025 (7)	0.0020 (7)
C17	0.0181 (10)	0.0213 (9)	0.0168 (9)	0.0050 (8)	0.0053 (7)	0.0037 (7)
C18	0.0174 (10)	0.0223 (10)	0.0200 (10)	0.0009 (8)	0.0023 (8)	0.0061 (8)
C19	0.0220 (10)	0.0150 (9)	0.0191 (9)	−0.0001 (7)	0.0021 (8)	0.0004 (7)
C20	0.0200 (10)	0.0158 (9)	0.0150 (9)	0.0032 (7)	0.0025 (7)	0.0007 (7)
C21	0.0247 (10)	0.0161 (9)	0.0208 (10)	0.0038 (8)	0.0093 (8)	−0.0011 (7)
C22	0.0280 (12)	0.0275 (11)	0.0404 (13)	−0.0035 (9)	0.0144 (10)	0.0048 (10)
C23	0.0302 (12)	0.0166 (9)	0.0250 (11)	0.0028 (8)	0.0109 (9)	−0.0035 (8)
C24	0.0176 (9)	0.0137 (8)	0.0161 (9)	−0.0026 (7)	0.0045 (7)	−0.0014 (7)
C25	0.0186 (10)	0.0141 (8)	0.0219 (10)	0.0020 (7)	0.0083 (8)	−0.0026 (7)
C26	0.0127 (9)	0.0175 (9)	0.0202 (9)	0.0000 (7)	0.0036 (7)	0.0002 (7)

Geometric parameters (Å, º)

I1—C24	2.0768 (19)	C12—H12A	0.9800
S1—C1	1.6973 (19)	C12—H12B	0.9800
F2—C26	1.348 (2)	C12—H12C	0.9800
C3—H3A	0.9900	C13—H13A	0.9800
C3—H3B	0.9900	C13—H13B	0.9800
C3—C4	1.530 (3)	C13—H13C	0.9800
C3—C2	1.516 (3)	C14—H14A	0.9800
F1—C25	1.346 (2)	C14—H14B	0.9800
C4—H4A	0.9900	C14—H14C	0.9800
C4—H4B	0.9900	C15—C16	1.398 (3)
C4—C5	1.523 (3)	C15—C20	1.397 (3)
N2—C5	1.481 (2)	C16—C17	1.388 (3)
N2—C1	1.354 (2)	C16—C21	1.508 (3)
N2—C15	1.446 (2)	C17—H17	0.9500
N1—C6	1.445 (2)	C17—C18	1.393 (3)
N1—C1	1.360 (2)	C18—C19	1.396 (3)
N1—C2	1.491 (2)	C18—C22	1.508 (3)
C7—C6	1.398 (3)	C19—H19	0.9500
C7—C8	1.392 (3)	C19—C20	1.393 (3)
C7—C12	1.507 (3)	C20—C23	1.508 (3)
C6—C11	1.401 (3)	C21—H21A	0.9800
C5—H5A	0.9900	C21—H21B	0.9800
C5—H5B	0.9900	C21—H21C	0.9800
C9—C8	1.391 (3)	C22—H22A	0.9800
C9—C10	1.390 (3)	C22—H22B	0.9800
C9—C13	1.510 (3)	C22—H22C	0.9800
C8—H8	0.9500	C23—H23A	0.9800
C2—H2A	0.9900	C23—H23B	0.9800
C2—H2B	0.9900	C23—H23C	0.9800
C10—H10	0.9500	C24—C25	1.380 (3)
C10—C11	1.393 (3)	C24—C26	1.382 (3)
C11—C14	1.503 (3)	C25—C26^i	1.380 (3)
H3A—C3—H3B	107.9	C9—C13—H13A	109.5
C4—C3—H3A	109.2	C9—C13—H13B	109.5
C4—C3—H3B	109.2	C9—C13—H13C	109.5
C2—C3—H3A	109.2	H13A—C13—H13B	109.5
C2—C3—H3B	109.2	H13A—C13—H13C	109.5
C2—C3—C4	111.94 (17)	H13B—C13—H13C	109.5
C3—C4—H4A	109.6	C11—C14—H14A	109.5
C3—C4—H4B	109.6	C11—C14—H14B	109.5
H4A—C4—H4B	108.2	C11—C14—H14C	109.5
C5—C4—C3	110.08 (16)	H14A—C14—H14B	109.5
C5—C4—H4A	109.6	H14A—C14—H14C	109.5
C5—C4—H4B	109.6	H14B—C14—H14C	109.5
C1—N2—C5	122.58 (16)	C16—C15—N2	119.22 (17)
C1—N2—C15	120.32 (15)	C20—C15—N2	119.38 (17)
C15—N2—C5	116.39 (15)	C20—C15—C16	121.35 (18)
C6—N1—C2	113.50 (15)	C15—C16—C21	120.97 (18)
C1—N1—C6	118.75 (15)	C17—C16—C15	118.37 (18)
C1—N1—C2	127.59 (16)	C17—C16—C21	120.65 (18)
C6—C7—C12	120.83 (18)	C16—C17—H17	119.0
C8—C7—C6	118.07 (18)	C16—C17—C18	121.96 (19)
C8—C7—C12	121.06 (18)	C18—C17—H17	119.0
C7—C6—N1	118.63 (17)	C17—C18—C19	118.21 (19)
C7—C6—C11	121.69 (18)	C17—C18—C22	120.7 (2)
C11—C6—N1	119.62 (17)	C19—C18—C22	121.04 (19)
C4—C5—H5A	109.1	C18—C19—H19	119.2
C4—C5—H5B	109.1	C20—C19—C18	121.63 (18)
N2—C5—C4	112.63 (15)	C20—C19—H19	119.2
N2—C5—H5A	109.1	C15—C20—C23	121.38 (18)
N2—C5—H5B	109.1	C19—C20—C15	118.43 (18)
H5A—C5—H5B	107.8	C19—C20—C23	120.18 (18)
N2—C1—S1	120.54 (14)	C16—C21—H21A	109.5
N2—C1—N1	119.04 (16)	C16—C21—H21B	109.5
N1—C1—S1	120.42 (14)	C16—C21—H21C	109.5
C8—C9—C13	120.9 (2)	H21A—C21—H21B	109.5
C10—C9—C8	118.41 (19)	H21A—C21—H21C	109.5
C10—C9—C13	120.6 (2)	H21B—C21—H21C	109.5
C7—C8—H8	119.0	C18—C22—H22A	109.5
C9—C8—C7	121.9 (2)	C18—C22—H22B	109.5
C9—C8—H8	119.0	C18—C22—H22C	109.5
C3—C2—H2A	108.6	H22A—C22—H22B	109.5
C3—C2—H2B	108.6	H22A—C22—H22C	109.5
N1—C2—C3	114.51 (16)	H22B—C22—H22C	109.5
N1—C2—H2A	108.6	C20—C23—H23A	109.5
N1—C2—H2B	108.6	C20—C23—H23B	109.5
H2A—C2—H2B	107.6	C20—C23—H23C	109.5
C9—C10—H10	119.0	H23A—C23—H23B	109.5
C9—C10—C11	121.96 (19)	H23A—C23—H23C	109.5
C11—C10—H10	119.0	H23B—C23—H23C	109.5
C6—C11—C14	121.03 (19)	C25—C24—I1	122.20 (14)
C10—C11—C6	117.93 (19)	C25—C24—C26	117.24 (17)
C10—C11—C14	120.99 (19)	C26—C24—I1	120.53 (14)
C7—C12—H12A	109.5	F1—C25—C24	120.20 (17)
C7—C12—H12B	109.5	F1—C25—C26^i	118.55 (18)
C7—C12—H12C	109.5	C24—C25—C26^i	121.25 (18)
H12A—C12—H12B	109.5	F2—C26—C24	119.99 (17)
H12A—C12—H12C	109.5	F2—C26—C25^i	118.50 (17)
H12B—C12—H12C	109.5	C25^i—C26—C24	121.51 (18)
I1—C24—C25—F1	−1.5 (3)	C8—C9—C10—C11	−1.4 (3)
I1—C24—C25—C26^i	177.90 (15)	C2—C3—C4—C5	−37.8 (2)
I1—C24—C26—F2	2.6 (3)	C2—N1—C6—C7	99.7 (2)
I1—C24—C26—C25^i	−177.94 (15)	C2—N1—C6—C11	−77.6 (2)
C3—C4—C5—N2	−48.2 (2)	C2—N1—C1—S1	160.45 (15)
C4—C3—C2—N1	80.6 (2)	C2—N1—C1—N2	−20.1 (3)
N2—C15—C16—C17	−175.28 (16)	C10—C9—C8—C7	1.6 (3)
N2—C15—C16—C21	6.2 (3)	C12—C7—C6—N1	4.0 (3)
N2—C15—C20—C19	176.04 (17)	C12—C7—C6—C11	−178.79 (18)
N2—C15—C20—C23	−5.0 (3)	C12—C7—C8—C9	177.33 (18)
N1—C6—C11—C10	178.49 (17)	C13—C9—C8—C7	−175.53 (19)
N1—C6—C11—C14	−4.0 (3)	C13—C9—C10—C11	175.7 (2)
C7—C6—C11—C10	1.3 (3)	C15—N2—C5—C4	−105.26 (19)
C7—C6—C11—C14	178.73 (18)	C15—N2—C1—S1	−10.1 (2)
C6—N1—C1—S1	−14.7 (2)	C15—N2—C1—N1	170.45 (16)
C6—N1—C1—N2	164.77 (16)	C15—C16—C17—C18	−0.8 (3)
C6—N1—C2—C3	149.76 (17)	C16—C15—C20—C19	−1.2 (3)
C6—C7—C8—C9	−0.4 (3)	C16—C15—C20—C23	177.77 (18)
C5—N2—C1—S1	159.96 (14)	C16—C17—C18—C19	−1.1 (3)
C5—N2—C1—N1	−19.5 (3)	C16—C17—C18—C22	178.75 (19)
C5—N2—C15—C16	103.2 (2)	C17—C18—C19—C20	1.9 (3)
C5—N2—C15—C20	−74.1 (2)	C18—C19—C20—C15	−0.8 (3)
C1—N2—C5—C4	84.3 (2)	C18—C19—C20—C23	−179.77 (19)
C1—N2—C15—C16	−86.2 (2)	C20—C15—C16—C17	2.0 (3)
C1—N2—C15—C20	96.5 (2)	C20—C15—C16—C21	−176.61 (17)
C1—N1—C6—C7	−84.5 (2)	C21—C16—C17—C18	177.80 (18)
C1—N1—C6—C11	98.2 (2)	C22—C18—C19—C20	−178.0 (2)
C1—N1—C2—C3	−25.6 (3)	C25—C24—C26—F2	−179.39 (17)
C9—C10—C11—C6	0.0 (3)	C25—C24—C26—C25^i	0.1 (3)
C9—C10—C11—C14	−177.48 (19)	C26—C24—C25—F1	−179.51 (17)
C8—C7—C6—N1	−178.33 (17)	C26—C24—C25—C26^i	−0.1 (3)
C8—C7—C6—C11	−1.1 (3)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···F2^ii	0.99	2.44	3.310 (2)	146
C2—H2B···S1^iii	0.99	2.91	3.898 (2)	173

Symmetry codes: (ii) x−1, y, z; (iii) x, −y+3/2, z+1/2.

(SDiazMesS_135F3I3B)

Crystal data

3(C6F3I3)·3(C23H30N2S)	F(000) = 5040
Mr = 2628.92	Dx = 1.914 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 39.226 (4) Å	Cell parameters from 9114 reflections
b = 7.9811 (9) Å	θ = 2.7–26.0°
c = 30.341 (4) Å	µ = 3.19 mm^−1
β = 106.162 (4)°	T = 100 K
V = 9123.3 (18) Å^3	Needle, colourless
Z = 4	0.34 × 0.05 × 0.05 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	15994 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.054
φ and ω scans	θmax = 26.1°, θmin = 2.2°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −46→48
Tmin = 0.625, Tmax = 0.745	k = −9→9
105324 measured reflections	l = −37→36
17944 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	H-atom parameters constrained
S = 1.27	w = 1/[σ^2(Fo^2) + 146.2483P] where P = (Fo^2 + 2Fc^2)/3
17944 reflections	(Δ/σ)max = 0.001
1064 parameters	Δρmax = 1.36 e Å^−3
36 restraints	Δρmin = −1.13 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
I1	0.17983 (2)	0.60761 (7)	0.24302 (2)	0.02195 (12)
I2	0.26052 (2)	0.33085 (8)	0.42738 (2)	0.03294 (15)
I3	0.33980 (2)	0.70126 (7)	0.31303 (2)	0.02390 (12)
I4	0.09592 (2)	0.60928 (7)	0.31138 (2)	0.01897 (11)
I5	0.18014 (2)	0.31948 (7)	0.49485 (2)	0.01975 (11)
I6	0.03400 (2)	0.60775 (7)	0.47380 (2)	0.02249 (12)
I7	0.33688 (2)	0.32337 (8)	0.56956 (2)	0.02727 (13)
I8	0.41843 (2)	0.62225 (7)	0.44655 (2)	0.02791 (13)
I9	0.49712 (2)	0.27904 (7)	0.62240 (2)	0.02750 (13)
S1	0.09289 (5)	0.7364 (2)	0.20907 (6)	0.0179 (4)
S2	0.25318 (5)	0.1634 (3)	0.55724 (7)	0.0214 (4)
S3	0.42010 (5)	−0.1297 (2)	0.32167 (6)	0.0159 (4)
F1	0.19920 (12)	0.4077 (7)	0.33644 (16)	0.0278 (11)
F2	0.32154 (12)	0.5048 (7)	0.39387 (16)	0.0276 (11)
F3	0.26055 (12)	0.6883 (6)	0.24578 (16)	0.0230 (10)
F4	0.15701 (12)	0.4352 (6)	0.39062 (15)	0.0224 (10)
F5	0.10977 (12)	0.4499 (6)	0.51654 (14)	0.0219 (10)
F6	0.04210 (12)	0.6477 (6)	0.37315 (16)	0.0240 (11)
F7	0.35567 (13)	0.5225 (7)	0.48909 (17)	0.0318 (12)
F8	0.47977 (13)	0.4791 (7)	0.52924 (18)	0.0316 (12)
F9	0.41692 (13)	0.2753 (6)	0.62890 (16)	0.0263 (11)
N1	0.07208 (17)	0.9446 (8)	0.1389 (2)	0.0179 (14)
N2	0.0671 (2)	1.0445 (9)	0.2085 (2)	0.0252 (16)
N3	0.24705 (18)	−0.1699 (9)	0.5498 (2)	0.0225 (15)
N4	0.24184 (17)	−0.0554 (9)	0.6179 (2)	0.0197 (14)
N5	0.40947 (18)	0.1114 (8)	0.2590 (2)	0.0202 (14)
N6	0.41815 (17)	0.2010 (8)	0.3343 (2)	0.0151 (13)
C1	0.0767 (2)	0.9211 (10)	0.1846 (3)	0.0174 (16)
C2	0.0710 (2)	1.1059 (11)	0.1138 (3)	0.0266 (19)
H2A	0.045899	1.136065	0.099050	0.032*
H2B	0.082815	1.090584	0.089218	0.032*
C3	0.0891 (3)	1.2518 (12)	0.1452 (3)	0.037 (2)
H3A	0.111394	1.211015	0.166796	0.045*
H3B	0.095337	1.341319	0.126186	0.045*
C4	0.0651 (3)	1.3240 (12)	0.1723 (3)	0.043 (3)
H4A	0.079703	1.381108	0.200151	0.052*
H4B	0.048802	1.407546	0.153341	0.052*
C5	0.0440 (3)	1.1851 (11)	0.1858 (3)	0.033 (2)
H5A	0.031008	1.230006	0.206918	0.040*
H5B	0.026246	1.142686	0.158062	0.040*
C6	0.0712 (2)	0.8008 (11)	0.1103 (3)	0.0204 (17)
C7	0.1009 (3)	0.7584 (13)	0.0951 (3)	0.032 (2)
C8	0.0981 (3)	0.6298 (15)	0.0649 (3)	0.044 (3)
H8	0.118005	0.602602	0.054303	0.053*
C9	0.0672 (3)	0.5364 (12)	0.0489 (3)	0.041 (3)
C10	0.0382 (3)	0.5768 (11)	0.0650 (3)	0.032 (2)
H10	0.017019	0.513016	0.054878	0.039*
C11	0.0397 (2)	0.7087 (10)	0.0955 (3)	0.0209 (17)
C12	0.1346 (2)	0.8496 (16)	0.1130 (3)	0.043 (3)
H12A	0.147797	0.801277	0.142511	0.065*
H12B	0.129694	0.967951	0.117169	0.065*
H12C	0.148836	0.839944	0.091146	0.065*
C13	0.0651 (5)	0.3969 (15)	0.0140 (4)	0.072 (5)
H13A	0.053515	0.298722	0.022884	0.108*
H13B	0.089126	0.366600	0.013165	0.108*
H13C	0.051357	0.435446	−0.016381	0.108*
C14	0.0086 (2)	0.7449 (12)	0.1141 (3)	0.028 (2)
H14A	−0.010565	0.664961	0.101057	0.042*
H14B	0.000029	0.859118	0.105620	0.042*
H14C	0.015965	0.734178	0.147553	0.042*
C15	0.0747 (2)	1.0402 (10)	0.2585 (3)	0.0216 (18)
C16	0.0461 (2)	0.9990 (11)	0.2757 (3)	0.0244 (18)
C17	0.0521 (3)	1.0092 (11)	0.3234 (3)	0.028 (2)
H17	0.033180	0.983736	0.336135	0.034*
C18	0.0841 (3)	1.0540 (11)	0.3523 (3)	0.034 (2)
C19	0.1118 (3)	1.0913 (11)	0.3339 (3)	0.031 (2)
H19	0.134250	1.121162	0.353940	0.037*
C20	0.1076 (2)	1.0860 (11)	0.2863 (3)	0.0259 (19)
C21	0.0113 (3)	0.9353 (13)	0.2459 (3)	0.034 (2)
H21A	−0.007652	0.962998	0.259955	0.052*
H21B	0.012561	0.813405	0.242658	0.052*
H21C	0.006247	0.987755	0.215542	0.052*
C22	0.0897 (3)	1.0617 (13)	0.4037 (3)	0.039 (2)
H22A	0.078763	1.163877	0.411507	0.059*
H22B	0.115173	1.062585	0.419328	0.059*
H22C	0.078731	0.963529	0.413651	0.059*
C23	0.1379 (3)	1.1296 (14)	0.2663 (3)	0.041 (3)
H23A	0.140989	1.039430	0.245821	0.061*
H23B	0.159869	1.142806	0.291255	0.061*
H23C	0.132554	1.234516	0.249027	0.061*
C24	0.2471 (2)	−0.0323 (11)	0.5761 (3)	0.0197 (17)
C25	0.2526 (3)	−0.3544 (15)	0.5606 (4)	0.022 (2)	0.717 (14)
H25A	0.265423	−0.405159	0.539974	0.027*	0.717 (14)
H25B	0.229303	−0.410526	0.554785	0.027*	0.717 (14)
C26	0.2737 (3)	−0.3823 (15)	0.6100 (4)	0.021 (2)	0.717 (14)
H26A	0.293930	−0.303153	0.618251	0.025*	0.717 (14)
H26B	0.283371	−0.497692	0.613659	0.025*	0.717 (14)
C27	0.2489 (3)	−0.3548 (12)	0.6437 (3)	0.040 (3)	0.717 (14)
H27A	0.234714	−0.457296	0.643878	0.048*	0.717 (14)
H27B	0.264066	−0.335896	0.675352	0.048*	0.717 (14)
C25B	0.2680 (9)	−0.310 (4)	0.5804 (11)	0.022 (4)	0.283 (14)
H25C	0.279248	−0.379329	0.561226	0.027*	0.283 (14)
H25D	0.287475	−0.256558	0.604276	0.027*	0.283 (14)
C26B	0.2487 (8)	−0.425 (4)	0.6040 (10)	0.021 (4)	0.283 (14)
H26C	0.224014	−0.442264	0.584917	0.025*	0.283 (14)
H26D	0.260681	−0.535819	0.609387	0.025*	0.283 (14)
C27B	0.2489 (3)	−0.3548 (12)	0.6437 (3)	0.040 (3)	0.283 (14)
H27C	0.273064	−0.317550	0.660673	0.048*	0.283 (14)
H27D	0.239904	−0.432974	0.663223	0.048*	0.283 (14)
C28	0.2241 (2)	−0.2068 (13)	0.6290 (3)	0.033 (2)
H28A	0.204784	−0.239241	0.601637	0.039*
H28B	0.213255	−0.179596	0.653876	0.039*
C29	0.2394 (3)	−0.1518 (11)	0.5006 (3)	0.029 (2)
C30	0.2036 (3)	−0.1523 (11)	0.4748 (3)	0.033 (2)
C31	0.1960 (4)	−0.1423 (12)	0.4271 (4)	0.046 (3)
H31	0.171917	−0.144533	0.409126	0.055*
C32	0.2222 (4)	−0.1294 (13)	0.4053 (4)	0.048 (3)
C33	0.2576 (4)	−0.1335 (11)	0.4317 (4)	0.050 (3)
H33	0.275722	−0.128316	0.416613	0.060*
C34	0.2676 (3)	−0.1454 (12)	0.4810 (4)	0.038 (2)
C35	0.1745 (2)	−0.1655 (11)	0.4962 (3)	0.032 (2)
H35A	0.177249	−0.268718	0.514368	0.048*
H35B	0.151803	−0.167798	0.472364	0.048*
H35C	0.175112	−0.068725	0.516321	0.048*
C36	0.2148 (4)	−0.1041 (16)	0.3544 (4)	0.067 (4)
H36A	0.192497	−0.160199	0.338563	0.101*
H36B	0.234217	−0.151629	0.343922	0.101*
H36C	0.212732	0.016002	0.347412	0.101*
C37	0.3051 (3)	−0.1484 (15)	0.5089 (5)	0.056 (4)
H37A	0.307389	−0.087180	0.537571	0.085*
H37B	0.319950	−0.095233	0.491750	0.085*
H37C	0.312661	−0.264695	0.515830	0.085*
C38	0.2466 (2)	0.0809 (11)	0.6516 (3)	0.0223 (18)
C39	0.2799 (2)	0.1049 (11)	0.6821 (3)	0.0215 (17)
C40	0.2817 (2)	0.2149 (11)	0.7180 (3)	0.0258 (19)
H40	0.304249	0.234108	0.739215	0.031*
C41	0.2529 (2)	0.2977 (11)	0.7249 (3)	0.0259 (19)
C42	0.2198 (2)	0.2732 (12)	0.6932 (3)	0.028 (2)
H42	0.199577	0.331298	0.696895	0.034*
C43	0.2161 (2)	0.1635 (12)	0.6561 (3)	0.0258 (19)
C44	0.3124 (2)	0.0187 (12)	0.6760 (3)	0.029 (2)
H44A	0.307102	−0.100078	0.669140	0.044*
H44B	0.331789	0.028983	0.704288	0.044*
H44C	0.319332	0.071008	0.650606	0.044*
C45	0.2553 (3)	0.4072 (13)	0.7661 (3)	0.036 (2)
H45A	0.257443	0.336673	0.793160	0.054*
H45B	0.233908	0.476275	0.760619	0.054*
H45C	0.276219	0.479845	0.771279	0.054*
C46	0.1799 (2)	0.1368 (13)	0.6222 (3)	0.033 (2)
H46A	0.167092	0.049633	0.633753	0.049*
H46B	0.182964	0.101852	0.592508	0.049*
H46C	0.166432	0.241623	0.618321	0.049*
C47	0.4162 (2)	0.0739 (11)	0.3039 (3)	0.0184 (16)
C48	0.3921 (2)	0.2719 (11)	0.2392 (3)	0.0264 (19)
H48A	0.374718	0.305475	0.255830	0.032*
H48B	0.378984	0.254183	0.206622	0.032*
C49	0.4189 (2)	0.4112 (10)	0.2426 (3)	0.0226 (18)
H49A	0.433152	0.389480	0.220949	0.027*
H49B	0.406369	0.519212	0.234181	0.027*
C50	0.4429 (2)	0.4211 (12)	0.2907 (3)	0.028 (2)
H50A	0.453250	0.534890	0.295980	0.034*
H50B	0.462619	0.340543	0.293940	0.034*
C51	0.4237 (2)	0.3828 (10)	0.3277 (3)	0.0220 (17)
H51A	0.437745	0.430735	0.357315	0.026*
H51B	0.400310	0.439402	0.319176	0.026*
C52	0.4131 (2)	−0.0127 (10)	0.2260 (3)	0.0193 (17)
C53	0.4467 (2)	−0.0513 (11)	0.2208 (3)	0.0219 (18)
C54	0.4481 (2)	−0.1629 (11)	0.1857 (3)	0.0232 (18)
H54	0.470583	−0.192918	0.181994	0.028*
C55	0.4176 (2)	−0.2313 (10)	0.1561 (3)	0.0225 (18)
C56	0.3851 (2)	−0.1928 (11)	0.1631 (3)	0.0248 (18)
H56	0.364293	−0.242455	0.143700	0.030*
C57	0.3819 (2)	−0.0829 (11)	0.1978 (3)	0.0254 (19)
C58	0.4793 (2)	0.0247 (13)	0.2509 (3)	0.034 (2)
H58A	0.479854	0.144329	0.243836	0.051*
H58B	0.500148	−0.030650	0.245805	0.051*
H58C	0.479396	0.010912	0.283042	0.051*
C59	0.4202 (3)	−0.3455 (11)	0.1178 (3)	0.028 (2)
H59A	0.427732	−0.280823	0.094702	0.042*
H59B	0.396976	−0.396176	0.103702	0.042*
H59C	0.437611	−0.433816	0.130068	0.042*
C60	0.3461 (2)	−0.0464 (13)	0.2038 (3)	0.031 (2)
H60A	0.335281	0.047153	0.183908	0.047*
H60B	0.348527	−0.016677	0.235893	0.047*
H60C	0.330992	−0.145863	0.195625	0.047*
C61	0.4160 (2)	0.1624 (10)	0.3802 (3)	0.0177 (16)
C62	0.3819 (2)	0.1475 (9)	0.3873 (3)	0.0183 (17)
C63	0.3803 (3)	0.1079 (11)	0.4312 (3)	0.030 (2)
H63	0.357796	0.096748	0.436894	0.036*
C64	0.4106 (3)	0.0845 (10)	0.4668 (3)	0.031 (2)
C65	0.4434 (3)	0.1088 (11)	0.4592 (3)	0.028 (2)
H65	0.464092	0.098498	0.484297	0.034*
C66	0.4471 (2)	0.1481 (10)	0.4158 (3)	0.0213 (17)
C67	0.3486 (2)	0.1714 (10)	0.3483 (3)	0.0266 (19)
H67A	0.327778	0.148776	0.359224	0.040*
H67B	0.348852	0.094058	0.323333	0.040*
H67C	0.347587	0.287030	0.337123	0.040*
C68	0.4071 (3)	0.0245 (12)	0.5125 (3)	0.043 (3)
H68A	0.430089	0.033908	0.535695	0.064*
H68B	0.399380	−0.092789	0.509904	0.064*
H68C	0.389526	0.093365	0.521671	0.064*
C69	0.4830 (2)	0.1758 (12)	0.4082 (3)	0.028 (2)
H69A	0.483346	0.127609	0.378625	0.042*
H69B	0.501282	0.121551	0.432866	0.042*
H69C	0.487883	0.296271	0.408221	0.042*
C70	0.2286 (2)	0.5507 (10)	0.2898 (3)	0.0198 (17)
C71	0.2296 (2)	0.4687 (10)	0.3308 (3)	0.0209 (17)
C72	0.2606 (2)	0.4503 (10)	0.3662 (3)	0.0221 (17)
C73	0.2914 (2)	0.5168 (10)	0.3599 (3)	0.0201 (17)
C74	0.2920 (2)	0.5976 (10)	0.3193 (3)	0.0198 (17)
C75	0.2606 (2)	0.6095 (10)	0.2850 (3)	0.0196 (17)
C76	0.0996 (2)	0.5435 (10)	0.3796 (3)	0.0163 (16)
C77	0.1304 (2)	0.4711 (10)	0.4078 (3)	0.0188 (16)
C78	0.1343 (2)	0.4380 (10)	0.4542 (3)	0.0171 (16)
C79	0.1065 (2)	0.4796 (10)	0.4717 (2)	0.0166 (16)
C80	0.0749 (2)	0.5486 (10)	0.4451 (3)	0.0162 (16)
C81	0.0726 (2)	0.5793 (10)	0.3991 (3)	0.0177 (16)
C82	0.3852 (2)	0.4017 (11)	0.5597 (3)	0.0216 (17)
C83	0.3866 (2)	0.4783 (10)	0.5193 (3)	0.0220 (18)
C84	0.4177 (2)	0.5104 (10)	0.5083 (3)	0.0212 (17)
C85	0.4490 (2)	0.4574 (10)	0.5396 (3)	0.0217 (17)
C86	0.4493 (2)	0.3797 (10)	0.5801 (3)	0.0202 (17)
C87	0.4175 (2)	0.3553 (10)	0.5903 (3)	0.0212 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0169 (2)	0.0273 (3)	0.0196 (3)	0.0010 (2)	0.0018 (2)	−0.0014 (2)
I2	0.0307 (3)	0.0400 (4)	0.0270 (3)	−0.0035 (3)	0.0063 (2)	0.0110 (3)
I3	0.0170 (3)	0.0230 (3)	0.0311 (3)	0.0005 (2)	0.0056 (2)	0.0066 (2)
I4	0.0224 (3)	0.0218 (3)	0.0135 (2)	0.0029 (2)	0.00617 (19)	0.0026 (2)
I5	0.0206 (3)	0.0184 (3)	0.0177 (3)	0.0004 (2)	0.0012 (2)	0.0017 (2)
I6	0.0219 (3)	0.0274 (3)	0.0207 (3)	−0.0021 (2)	0.0102 (2)	−0.0061 (2)
I7	0.0199 (3)	0.0327 (3)	0.0307 (3)	0.0047 (2)	0.0096 (2)	0.0021 (3)
I8	0.0390 (3)	0.0244 (3)	0.0220 (3)	0.0029 (3)	0.0113 (2)	−0.0020 (2)
I9	0.0195 (3)	0.0256 (3)	0.0331 (3)	−0.0014 (2)	0.0002 (2)	0.0026 (2)
S1	0.0225 (10)	0.0163 (9)	0.0141 (9)	0.0042 (8)	0.0037 (7)	0.0041 (7)
S2	0.0176 (10)	0.0240 (11)	0.0211 (10)	−0.0012 (8)	0.0030 (8)	0.0063 (8)
S3	0.0159 (9)	0.0142 (9)	0.0167 (9)	0.0011 (7)	0.0032 (7)	−0.0007 (7)
F1	0.020 (2)	0.043 (3)	0.023 (3)	−0.008 (2)	0.009 (2)	0.003 (2)
F2	0.021 (2)	0.033 (3)	0.024 (3)	−0.004 (2)	−0.001 (2)	0.004 (2)
F3	0.021 (2)	0.027 (3)	0.021 (2)	−0.001 (2)	0.0053 (19)	0.005 (2)
F4	0.017 (2)	0.032 (3)	0.018 (2)	0.005 (2)	0.0059 (19)	0.001 (2)
F5	0.028 (3)	0.028 (3)	0.010 (2)	−0.005 (2)	0.0043 (18)	0.0003 (19)
F6	0.017 (2)	0.030 (3)	0.023 (2)	0.005 (2)	0.0025 (19)	0.005 (2)
F7	0.022 (3)	0.042 (3)	0.027 (3)	0.007 (2)	0.001 (2)	0.004 (2)
F8	0.026 (3)	0.034 (3)	0.039 (3)	−0.002 (2)	0.016 (2)	0.000 (2)
F9	0.027 (3)	0.029 (3)	0.022 (2)	0.001 (2)	0.004 (2)	0.005 (2)
N1	0.019 (3)	0.017 (3)	0.018 (3)	0.003 (3)	0.004 (3)	0.004 (3)
N2	0.037 (4)	0.016 (3)	0.023 (4)	0.005 (3)	0.010 (3)	0.004 (3)
N3	0.019 (3)	0.019 (4)	0.030 (4)	0.005 (3)	0.008 (3)	0.008 (3)
N4	0.011 (3)	0.027 (4)	0.019 (3)	−0.003 (3)	0.000 (3)	0.006 (3)
N5	0.027 (4)	0.016 (3)	0.018 (3)	0.002 (3)	0.008 (3)	−0.002 (3)
N6	0.017 (3)	0.017 (3)	0.013 (3)	0.001 (3)	0.006 (3)	0.000 (3)
C1	0.017 (4)	0.018 (4)	0.019 (4)	−0.003 (3)	0.008 (3)	0.004 (3)
C2	0.029 (5)	0.031 (5)	0.017 (4)	0.002 (4)	0.001 (3)	0.011 (4)
C3	0.047 (6)	0.027 (5)	0.035 (5)	−0.012 (5)	0.007 (5)	0.013 (4)
C4	0.080 (8)	0.021 (5)	0.025 (5)	0.002 (5)	0.008 (5)	0.004 (4)
C5	0.051 (6)	0.022 (5)	0.026 (5)	0.012 (4)	0.010 (4)	0.004 (4)
C6	0.025 (4)	0.025 (4)	0.011 (4)	0.014 (4)	0.005 (3)	0.009 (3)
C7	0.040 (5)	0.043 (6)	0.016 (4)	0.021 (5)	0.012 (4)	0.022 (4)
C8	0.060 (7)	0.059 (7)	0.020 (5)	0.044 (6)	0.025 (5)	0.019 (5)
C9	0.081 (9)	0.023 (5)	0.020 (5)	0.024 (5)	0.014 (5)	0.004 (4)
C10	0.061 (7)	0.019 (4)	0.014 (4)	0.004 (4)	0.007 (4)	0.006 (3)
C11	0.030 (5)	0.018 (4)	0.012 (4)	0.002 (3)	0.002 (3)	0.007 (3)
C12	0.026 (5)	0.079 (8)	0.023 (5)	0.019 (5)	0.004 (4)	0.023 (5)
C13	0.160 (15)	0.037 (7)	0.025 (6)	0.042 (8)	0.035 (8)	0.006 (5)
C14	0.029 (5)	0.031 (5)	0.020 (4)	−0.007 (4)	0.001 (4)	0.003 (4)
C15	0.038 (5)	0.012 (4)	0.014 (4)	0.006 (3)	0.007 (3)	0.002 (3)
C16	0.036 (5)	0.021 (4)	0.018 (4)	0.001 (4)	0.010 (4)	0.002 (3)
C17	0.040 (5)	0.024 (5)	0.023 (4)	0.004 (4)	0.013 (4)	−0.004 (4)
C18	0.060 (7)	0.019 (4)	0.025 (5)	0.006 (4)	0.016 (5)	0.000 (4)
C19	0.046 (6)	0.013 (4)	0.026 (5)	−0.004 (4)	0.000 (4)	−0.007 (4)
C20	0.038 (5)	0.019 (4)	0.025 (4)	−0.005 (4)	0.016 (4)	−0.002 (4)
C21	0.034 (5)	0.040 (6)	0.029 (5)	0.002 (4)	0.007 (4)	−0.003 (4)
C22	0.066 (7)	0.028 (5)	0.024 (5)	−0.001 (5)	0.014 (5)	−0.002 (4)
C23	0.045 (6)	0.048 (6)	0.028 (5)	−0.023 (5)	0.007 (4)	−0.005 (5)
C24	0.011 (4)	0.027 (4)	0.018 (4)	0.000 (3)	−0.001 (3)	0.007 (3)
C25	0.025 (5)	0.018 (5)	0.021 (5)	0.005 (4)	0.001 (4)	−0.004 (4)
C26	0.025 (5)	0.015 (5)	0.018 (5)	0.004 (4)	0.001 (4)	−0.005 (4)
C27	0.072 (8)	0.020 (5)	0.025 (5)	−0.014 (5)	0.007 (5)	0.001 (4)
C25B	0.027 (7)	0.015 (7)	0.020 (7)	0.006 (6)	−0.001 (6)	−0.004 (6)
C26B	0.024 (7)	0.015 (7)	0.020 (7)	0.007 (6)	0.000 (6)	−0.005 (6)
C27B	0.072 (8)	0.020 (5)	0.025 (5)	−0.014 (5)	0.007 (5)	0.001 (4)
C28	0.024 (5)	0.047 (6)	0.026 (5)	−0.020 (4)	0.004 (4)	0.006 (4)
C29	0.051 (6)	0.016 (4)	0.025 (5)	−0.001 (4)	0.021 (4)	−0.001 (4)
C30	0.053 (6)	0.015 (4)	0.026 (5)	−0.001 (4)	0.004 (4)	−0.002 (4)
C31	0.079 (8)	0.023 (5)	0.032 (6)	0.006 (5)	0.009 (6)	−0.007 (4)
C32	0.083 (9)	0.025 (5)	0.031 (6)	0.006 (6)	0.009 (6)	−0.003 (4)
C33	0.102 (10)	0.009 (4)	0.059 (7)	0.007 (5)	0.054 (8)	0.004 (5)
C34	0.056 (7)	0.017 (5)	0.054 (7)	0.005 (4)	0.035 (6)	0.004 (4)
C35	0.030 (5)	0.017 (4)	0.041 (6)	−0.005 (4)	−0.002 (4)	0.002 (4)
C36	0.131 (13)	0.043 (7)	0.029 (6)	0.007 (8)	0.024 (7)	−0.011 (5)
C37	0.074 (9)	0.038 (6)	0.082 (9)	0.011 (6)	0.062 (8)	0.013 (6)
C38	0.025 (4)	0.023 (4)	0.020 (4)	0.005 (4)	0.008 (3)	0.007 (3)
C39	0.018 (4)	0.029 (5)	0.017 (4)	−0.003 (3)	0.002 (3)	0.007 (4)
C40	0.027 (5)	0.024 (4)	0.026 (4)	−0.001 (4)	0.007 (4)	0.011 (4)
C41	0.034 (5)	0.019 (4)	0.028 (5)	−0.003 (4)	0.013 (4)	0.009 (4)
C42	0.027 (5)	0.028 (5)	0.032 (5)	−0.002 (4)	0.011 (4)	0.013 (4)
C43	0.021 (4)	0.035 (5)	0.022 (4)	0.001 (4)	0.006 (3)	0.008 (4)
C44	0.014 (4)	0.038 (5)	0.031 (5)	−0.006 (4)	−0.001 (4)	0.000 (4)
C45	0.048 (6)	0.033 (5)	0.027 (5)	−0.009 (5)	0.011 (4)	−0.003 (4)
C46	0.021 (4)	0.044 (6)	0.030 (5)	0.011 (4)	0.004 (4)	0.011 (4)
C47	0.014 (4)	0.026 (4)	0.015 (4)	0.001 (3)	0.005 (3)	0.001 (3)
C48	0.028 (5)	0.027 (5)	0.024 (4)	0.009 (4)	0.007 (4)	0.009 (4)
C49	0.027 (4)	0.020 (4)	0.023 (4)	0.004 (3)	0.009 (3)	0.008 (3)
C50	0.034 (5)	0.026 (5)	0.028 (5)	−0.003 (4)	0.014 (4)	−0.001 (4)
C51	0.030 (5)	0.015 (4)	0.020 (4)	−0.002 (3)	0.007 (3)	−0.001 (3)
C52	0.032 (5)	0.014 (4)	0.016 (4)	0.003 (3)	0.015 (3)	0.001 (3)
C53	0.028 (4)	0.027 (4)	0.009 (4)	−0.004 (4)	0.001 (3)	0.000 (3)
C54	0.029 (5)	0.025 (4)	0.017 (4)	0.004 (4)	0.009 (3)	0.000 (3)
C55	0.031 (5)	0.018 (4)	0.020 (4)	0.006 (4)	0.011 (4)	−0.004 (3)
C56	0.029 (5)	0.029 (5)	0.018 (4)	0.000 (4)	0.009 (3)	0.004 (4)
C57	0.034 (5)	0.026 (5)	0.017 (4)	0.005 (4)	0.008 (4)	0.004 (4)
C58	0.022 (5)	0.043 (6)	0.037 (5)	−0.003 (4)	0.010 (4)	−0.016 (5)
C59	0.040 (5)	0.026 (5)	0.021 (4)	0.004 (4)	0.014 (4)	−0.010 (4)
C60	0.024 (5)	0.042 (6)	0.025 (5)	0.000 (4)	0.004 (4)	−0.004 (4)
C61	0.023 (4)	0.013 (4)	0.017 (4)	0.002 (3)	0.006 (3)	−0.001 (3)
C62	0.031 (4)	0.011 (4)	0.020 (4)	0.000 (3)	0.018 (3)	0.000 (3)
C63	0.042 (5)	0.021 (4)	0.035 (5)	0.003 (4)	0.024 (4)	0.001 (4)
C64	0.064 (7)	0.010 (4)	0.024 (5)	0.004 (4)	0.019 (5)	0.001 (3)
C65	0.049 (6)	0.016 (4)	0.013 (4)	0.013 (4)	0.000 (4)	−0.001 (3)
C66	0.033 (5)	0.008 (4)	0.022 (4)	0.000 (3)	0.007 (4)	−0.005 (3)
C67	0.033 (5)	0.012 (4)	0.036 (5)	−0.006 (4)	0.012 (4)	−0.004 (4)
C68	0.091 (9)	0.020 (5)	0.021 (5)	−0.003 (5)	0.021 (5)	−0.003 (4)
C69	0.027 (5)	0.027 (5)	0.023 (4)	0.012 (4)	−0.004 (4)	−0.003 (4)
C70	0.021 (4)	0.017 (4)	0.022 (4)	0.004 (3)	0.007 (3)	−0.004 (3)
C71	0.016 (4)	0.020 (4)	0.029 (4)	−0.001 (3)	0.011 (3)	−0.001 (4)
C72	0.028 (4)	0.018 (4)	0.021 (4)	−0.002 (3)	0.010 (3)	−0.003 (3)
C73	0.017 (4)	0.020 (4)	0.022 (4)	0.001 (3)	0.003 (3)	−0.002 (3)
C74	0.014 (4)	0.021 (4)	0.025 (4)	0.000 (3)	0.007 (3)	0.001 (3)
C75	0.020 (4)	0.021 (4)	0.016 (4)	0.003 (3)	0.003 (3)	0.003 (3)
C76	0.019 (4)	0.018 (4)	0.014 (4)	−0.002 (3)	0.007 (3)	0.003 (3)
C77	0.021 (4)	0.019 (4)	0.016 (4)	−0.002 (3)	0.005 (3)	0.004 (3)
C78	0.020 (4)	0.013 (4)	0.019 (4)	−0.003 (3)	0.007 (3)	0.003 (3)
C79	0.021 (4)	0.020 (4)	0.008 (3)	−0.003 (3)	0.003 (3)	−0.002 (3)
C80	0.021 (4)	0.017 (4)	0.013 (4)	−0.005 (3)	0.008 (3)	−0.003 (3)
C81	0.022 (4)	0.015 (4)	0.016 (4)	0.001 (3)	0.005 (3)	0.004 (3)
C82	0.014 (4)	0.020 (4)	0.031 (5)	0.002 (3)	0.007 (3)	−0.005 (4)
C83	0.022 (4)	0.019 (4)	0.021 (4)	0.006 (3)	−0.001 (3)	−0.007 (3)
C84	0.030 (5)	0.010 (4)	0.025 (4)	0.001 (3)	0.011 (4)	−0.006 (3)
C85	0.024 (4)	0.015 (4)	0.028 (4)	0.000 (3)	0.010 (4)	−0.004 (3)
C86	0.017 (4)	0.017 (4)	0.024 (4)	0.003 (3)	0.001 (3)	−0.003 (3)
C87	0.022 (4)	0.020 (4)	0.019 (4)	−0.003 (3)	0.001 (3)	0.000 (3)

Geometric parameters (Å, º)

I1—C70	2.090 (8)	C28—H28B	0.9900
I2—C72	2.088 (8)	C29—C30	1.407 (14)
I3—C74	2.105 (8)	C29—C34	1.394 (13)
I4—C76	2.099 (7)	C30—C31	1.397 (14)
I5—C78	2.102 (8)	C30—C35	1.464 (14)
I6—C80	2.082 (8)	C31—H31	0.9500
I7—C82	2.096 (8)	C31—C32	1.374 (17)
I8—C84	2.083 (8)	C32—C33	1.395 (18)
I9—C86	2.114 (8)	C32—C36	1.504 (15)
S1—C1	1.693 (8)	C33—H33	0.9500
S2—C24	1.702 (8)	C33—C34	1.438 (16)
S3—C47	1.706 (9)	C34—C37	1.477 (17)
F1—C71	1.344 (9)	C35—H35A	0.9800
F2—C73	1.338 (9)	C35—H35B	0.9800
F3—C75	1.346 (9)	C35—H35C	0.9800
F4—C77	1.321 (9)	C36—H36A	0.9800
F5—C79	1.350 (8)	C36—H36B	0.9800
F6—C81	1.350 (9)	C36—H36C	0.9800
F7—C83	1.348 (9)	C37—H37A	0.9800
F8—C85	1.341 (9)	C37—H37B	0.9800
F9—C87	1.340 (9)	C37—H37C	0.9800
N1—C1	1.362 (10)	C38—C39	1.387 (11)
N1—C2	1.491 (10)	C38—C43	1.404 (12)
N1—C6	1.433 (11)	C39—C40	1.386 (12)
N2—C1	1.337 (11)	C39—C44	1.504 (12)
N2—C5	1.485 (11)	C40—H40	0.9500
N2—C15	1.461 (10)	C40—C41	1.373 (12)
N3—C24	1.356 (11)	C41—C42	1.400 (13)
N3—C25	1.510 (13)	C41—C45	1.506 (13)
N3—C25B	1.54 (3)	C42—H42	0.9500
N3—C29	1.447 (11)	C42—C43	1.403 (13)
N4—C24	1.355 (10)	C43—C46	1.518 (12)
N4—C28	1.478 (11)	C44—H44A	0.9800
N4—C38	1.468 (11)	C44—H44B	0.9800
N5—C47	1.347 (10)	C44—H44C	0.9800
N5—C48	1.496 (11)	C45—H45A	0.9800
N5—C52	1.443 (10)	C45—H45B	0.9800
N6—C47	1.359 (10)	C45—H45C	0.9800
N6—C51	1.488 (10)	C46—H46A	0.9800
N6—C61	1.453 (10)	C46—H46B	0.9800
C2—H2A	0.9900	C46—H46C	0.9800
C2—H2B	0.9900	C48—H48A	0.9900
C2—C3	1.547 (13)	C48—H48B	0.9900
C3—H3A	0.9900	C48—C49	1.514 (12)
C3—H3B	0.9900	C49—H49A	0.9900
C3—C4	1.525 (15)	C49—H49B	0.9900
C4—H4A	0.9900	C49—C50	1.501 (12)
C4—H4B	0.9900	C50—H50A	0.9900
C4—C5	1.508 (14)	C50—H50B	0.9900
C5—H5A	0.9900	C50—C51	1.548 (11)
C5—H5B	0.9900	C51—H51A	0.9900
C6—C7	1.407 (12)	C51—H51B	0.9900
C6—C11	1.402 (12)	C52—C53	1.404 (12)
C7—C8	1.360 (15)	C52—C57	1.402 (12)
C7—C12	1.475 (15)	C53—C54	1.400 (11)
C8—H8	0.9500	C53—C58	1.478 (12)
C8—C9	1.389 (17)	C54—H54	0.9500
C9—C10	1.393 (15)	C54—C55	1.392 (12)
C9—C13	1.523 (14)	C55—C56	1.383 (12)
C10—H10	0.9500	C55—C59	1.502 (11)
C10—C11	1.393 (12)	C56—H56	0.9500
C11—C14	1.508 (12)	C56—C57	1.404 (12)
C12—H12A	0.9800	C57—C60	1.494 (12)
C12—H12B	0.9800	C58—H58A	0.9800
C12—H12C	0.9800	C58—H58B	0.9800
C13—H13A	0.9800	C58—H58C	0.9800
C13—H13B	0.9800	C59—H59A	0.9800
C13—H13C	0.9800	C59—H59B	0.9800
C14—H14A	0.9800	C59—H59C	0.9800
C14—H14B	0.9800	C60—H60A	0.9800
C14—H14C	0.9800	C60—H60B	0.9800
C15—C16	1.400 (12)	C60—H60C	0.9800
C15—C20	1.382 (12)	C61—C62	1.415 (11)
C16—C17	1.403 (12)	C61—C66	1.392 (11)
C16—C21	1.503 (13)	C62—C63	1.388 (11)
C17—H17	0.9500	C62—C67	1.512 (12)
C17—C18	1.360 (14)	C63—H63	0.9500
C18—C19	1.386 (14)	C63—C64	1.377 (14)
C18—C22	1.517 (12)	C64—C65	1.381 (14)
C19—H19	0.9500	C64—C68	1.511 (12)
C19—C20	1.406 (12)	C65—H65	0.9500
C20—C23	1.520 (13)	C65—C66	1.399 (12)
C21—H21A	0.9800	C66—C69	1.506 (12)
C21—H21B	0.9800	C67—H67A	0.9800
C21—H21C	0.9800	C67—H67B	0.9800
C22—H22A	0.9800	C67—H67C	0.9800
C22—H22B	0.9800	C68—H68A	0.9800
C22—H22C	0.9800	C68—H68B	0.9800
C23—H23A	0.9800	C68—H68C	0.9800
C23—H23B	0.9800	C69—H69A	0.9800
C23—H23C	0.9800	C69—H69B	0.9800
C25—H25A	0.9900	C69—H69C	0.9800
C25—H25B	0.9900	C70—C71	1.394 (12)
C25—C26	1.514 (16)	C70—C75	1.386 (11)
C26—H26A	0.9900	C71—C72	1.388 (12)
C26—H26B	0.9900	C72—C73	1.381 (11)
C26—C27	1.612 (16)	C73—C74	1.396 (11)
C27—H27A	0.9900	C74—C75	1.377 (11)
C27—H27B	0.9900	C76—C77	1.395 (11)
C27—C28	1.516 (15)	C76—C81	1.382 (11)
C25B—H25C	0.9900	C77—C78	1.400 (11)
C25B—H25D	0.9900	C78—C79	1.379 (11)
C25B—C26B	1.50 (5)	C79—C80	1.390 (11)
C26B—H26C	0.9900	C80—C81	1.396 (10)
C26B—H26D	0.9900	C82—C83	1.384 (12)
C26B—C27B	1.33 (3)	C82—C87	1.395 (11)
C27B—H27C	0.9900	C83—C84	1.374 (12)
C27B—H27D	0.9900	C84—C85	1.392 (12)
C27B—C28	1.516 (15)	C85—C86	1.372 (12)
C28—H28A	0.9900	C86—C87	1.383 (11)
C1—N1—C2	128.0 (7)	C34—C37—H37A	109.5
C1—N1—C6	118.8 (6)	C34—C37—H37B	109.5
C6—N1—C2	112.9 (6)	C34—C37—H37C	109.5
C1—N2—C5	122.1 (7)	H37A—C37—H37B	109.5
C1—N2—C15	122.5 (7)	H37A—C37—H37C	109.5
C15—N2—C5	114.9 (7)	H37B—C37—H37C	109.5
C24—N3—C25	133.3 (8)	C39—C38—N4	118.6 (7)
C24—N3—C25B	108.7 (14)	C39—C38—C43	122.7 (8)
C24—N3—C29	119.4 (7)	C43—C38—N4	117.9 (8)
C29—N3—C25	107.2 (7)	C38—C39—C44	121.8 (8)
C29—N3—C25B	128.2 (13)	C40—C39—C38	116.4 (8)
C24—N4—C28	121.8 (7)	C40—C39—C44	121.7 (8)
C24—N4—C38	122.0 (7)	C39—C40—H40	118.0
C38—N4—C28	115.1 (7)	C41—C40—C39	124.0 (8)
C47—N5—C48	122.3 (7)	C41—C40—H40	118.0
C47—N5—C52	121.3 (7)	C40—C41—C42	118.3 (9)
C52—N5—C48	115.6 (6)	C40—C41—C45	122.8 (9)
C47—N6—C51	128.3 (7)	C42—C41—C45	118.8 (9)
C47—N6—C61	119.1 (6)	C41—C42—H42	119.8
C61—N6—C51	112.6 (6)	C41—C42—C43	120.4 (9)
N1—C1—S1	119.5 (6)	C43—C42—H42	119.8
N2—C1—S1	122.2 (6)	C38—C43—C46	121.9 (8)
N2—C1—N1	118.3 (7)	C42—C43—C38	118.1 (8)
N1—C2—H2A	109.0	C42—C43—C46	119.9 (8)
N1—C2—H2B	109.0	C39—C44—H44A	109.5
N1—C2—C3	113.1 (7)	C39—C44—H44B	109.5
H2A—C2—H2B	107.8	C39—C44—H44C	109.5
C3—C2—H2A	109.0	H44A—C44—H44B	109.5
C3—C2—H2B	109.0	H44A—C44—H44C	109.5
C2—C3—H3A	109.3	H44B—C44—H44C	109.5
C2—C3—H3B	109.3	C41—C45—H45A	109.5
H3A—C3—H3B	108.0	C41—C45—H45B	109.5
C4—C3—C2	111.6 (8)	C41—C45—H45C	109.5
C4—C3—H3A	109.3	H45A—C45—H45B	109.5
C4—C3—H3B	109.3	H45A—C45—H45C	109.5
C3—C4—H4A	109.7	H45B—C45—H45C	109.5
C3—C4—H4B	109.7	C43—C46—H46A	109.5
H4A—C4—H4B	108.2	C43—C46—H46B	109.5
C5—C4—C3	109.7 (8)	C43—C46—H46C	109.5
C5—C4—H4A	109.7	H46A—C46—H46B	109.5
C5—C4—H4B	109.7	H46A—C46—H46C	109.5
N2—C5—C4	111.8 (8)	H46B—C46—H46C	109.5
N2—C5—H5A	109.3	N5—C47—S3	120.4 (6)
N2—C5—H5B	109.3	N5—C47—N6	118.7 (7)
C4—C5—H5A	109.3	N6—C47—S3	120.9 (6)
C4—C5—H5B	109.3	N5—C48—H48A	109.3
H5A—C5—H5B	107.9	N5—C48—H48B	109.3
C7—C6—N1	120.7 (8)	N5—C48—C49	111.8 (7)
C11—C6—N1	118.9 (7)	H48A—C48—H48B	107.9
C11—C6—C7	120.3 (8)	C49—C48—H48A	109.3
C6—C7—C12	120.0 (9)	C49—C48—H48B	109.3
C8—C7—C6	118.9 (10)	C48—C49—H49A	109.7
C8—C7—C12	121.1 (9)	C48—C49—H49B	109.7
C7—C8—H8	118.7	H49A—C49—H49B	108.2
C7—C8—C9	122.7 (9)	C50—C49—C48	109.9 (7)
C9—C8—H8	118.7	C50—C49—H49A	109.7
C8—C9—C10	118.1 (9)	C50—C49—H49B	109.7
C8—C9—C13	120.5 (11)	C49—C50—H50A	108.9
C10—C9—C13	121.4 (12)	C49—C50—H50B	108.9
C9—C10—H10	119.3	C49—C50—C51	113.3 (7)
C9—C10—C11	121.4 (10)	H50A—C50—H50B	107.7
C11—C10—H10	119.3	C51—C50—H50A	108.9
C6—C11—C14	120.9 (7)	C51—C50—H50B	108.9
C10—C11—C6	118.6 (8)	N6—C51—C50	114.1 (7)
C10—C11—C14	120.4 (8)	N6—C51—H51A	108.7
C7—C12—H12A	109.5	N6—C51—H51B	108.7
C7—C12—H12B	109.5	C50—C51—H51A	108.7
C7—C12—H12C	109.5	C50—C51—H51B	108.7
H12A—C12—H12B	109.5	H51A—C51—H51B	107.6
H12A—C12—H12C	109.5	C53—C52—N5	120.4 (7)
H12B—C12—H12C	109.5	C57—C52—N5	117.2 (7)
C9—C13—H13A	109.5	C57—C52—C53	122.2 (7)
C9—C13—H13B	109.5	C52—C53—C58	121.1 (8)
C9—C13—H13C	109.5	C54—C53—C52	117.5 (8)
H13A—C13—H13B	109.5	C54—C53—C58	121.4 (8)
H13A—C13—H13C	109.5	C53—C54—H54	119.0
H13B—C13—H13C	109.5	C55—C54—C53	122.1 (8)
C11—C14—H14A	109.5	C55—C54—H54	119.0
C11—C14—H14B	109.5	C54—C55—C59	120.3 (8)
C11—C14—H14C	109.5	C56—C55—C54	118.5 (8)
H14A—C14—H14B	109.5	C56—C55—C59	121.1 (8)
H14A—C14—H14C	109.5	C55—C56—H56	118.9
H14B—C14—H14C	109.5	C55—C56—C57	122.2 (8)
C16—C15—N2	116.1 (8)	C57—C56—H56	118.9
C20—C15—N2	121.0 (8)	C52—C57—C56	117.5 (8)
C20—C15—C16	122.7 (8)	C52—C57—C60	122.7 (8)
C15—C16—C17	116.8 (8)	C56—C57—C60	119.9 (8)
C15—C16—C21	122.8 (8)	C53—C58—H58A	109.5
C17—C16—C21	120.3 (8)	C53—C58—H58B	109.5
C16—C17—H17	118.7	C53—C58—H58C	109.5
C18—C17—C16	122.6 (9)	H58A—C58—H58B	109.5
C18—C17—H17	118.7	H58A—C58—H58C	109.5
C17—C18—C19	118.9 (9)	H58B—C58—H58C	109.5
C17—C18—C22	121.1 (9)	C55—C59—H59A	109.5
C19—C18—C22	120.0 (10)	C55—C59—H59B	109.5
C18—C19—H19	119.2	C55—C59—H59C	109.5
C18—C19—C20	121.6 (9)	H59A—C59—H59B	109.5
C20—C19—H19	119.2	H59A—C59—H59C	109.5
C15—C20—C19	117.4 (8)	H59B—C59—H59C	109.5
C15—C20—C23	121.2 (8)	C57—C60—H60A	109.5
C19—C20—C23	121.4 (9)	C57—C60—H60B	109.5
C16—C21—H21A	109.5	C57—C60—H60C	109.5
C16—C21—H21B	109.5	H60A—C60—H60B	109.5
C16—C21—H21C	109.5	H60A—C60—H60C	109.5
H21A—C21—H21B	109.5	H60B—C60—H60C	109.5
H21A—C21—H21C	109.5	C62—C61—N6	118.3 (7)
H21B—C21—H21C	109.5	C66—C61—N6	119.3 (7)
C18—C22—H22A	109.5	C66—C61—C62	122.4 (7)
C18—C22—H22B	109.5	C61—C62—C67	121.2 (7)
C18—C22—H22C	109.5	C63—C62—C61	117.6 (8)
H22A—C22—H22B	109.5	C63—C62—C67	121.3 (8)
H22A—C22—H22C	109.5	C62—C63—H63	119.3
H22B—C22—H22C	109.5	C64—C63—C62	121.5 (9)
C20—C23—H23A	109.5	C64—C63—H63	119.3
C20—C23—H23B	109.5	C63—C64—C65	119.4 (8)
C20—C23—H23C	109.5	C63—C64—C68	118.9 (10)
H23A—C23—H23B	109.5	C65—C64—C68	121.7 (9)
H23A—C23—H23C	109.5	C64—C65—H65	118.9
H23B—C23—H23C	109.5	C64—C65—C66	122.3 (8)
N3—C24—S2	121.6 (6)	C66—C65—H65	118.9
N4—C24—S2	120.7 (7)	C61—C66—C65	116.7 (8)
N4—C24—N3	117.7 (7)	C61—C66—C69	121.7 (7)
N3—C25—H25A	109.4	C65—C66—C69	121.7 (8)
N3—C25—H25B	109.4	C62—C67—H67A	109.5
N3—C25—C26	111.3 (10)	C62—C67—H67B	109.5
H25A—C25—H25B	108.0	C62—C67—H67C	109.5
C26—C25—H25A	109.4	H67A—C67—H67B	109.5
C26—C25—H25B	109.4	H67A—C67—H67C	109.5
C25—C26—H26A	109.6	H67B—C67—H67C	109.5
C25—C26—H26B	109.6	C64—C68—H68A	109.5
C25—C26—C27	110.4 (9)	C64—C68—H68B	109.5
H26A—C26—H26B	108.1	C64—C68—H68C	109.5
C27—C26—H26A	109.6	H68A—C68—H68B	109.5
C27—C26—H26B	109.6	H68A—C68—H68C	109.5
C26—C27—H27A	109.3	H68B—C68—H68C	109.5
C26—C27—H27B	109.3	C66—C69—H69A	109.5
H27A—C27—H27B	107.9	C66—C69—H69B	109.5
C28—C27—C26	111.7 (8)	C66—C69—H69C	109.5
C28—C27—H27A	109.3	H69A—C69—H69B	109.5
C28—C27—H27B	109.3	H69A—C69—H69C	109.5
N3—C25B—H25C	107.7	H69B—C69—H69C	109.5
N3—C25B—H25D	107.7	C71—C70—I1	120.1 (6)
H25C—C25B—H25D	107.1	C75—C70—I1	122.7 (6)
C26B—C25B—N3	119 (2)	C75—C70—C71	116.7 (7)
C26B—C25B—H25C	107.7	F1—C71—C70	118.5 (7)
C26B—C25B—H25D	107.7	F1—C71—C72	118.6 (7)
C25B—C26B—H26C	110.3	C72—C71—C70	122.8 (7)
C25B—C26B—H26D	110.3	C71—C72—I2	121.3 (6)
H26C—C26B—H26D	108.5	C73—C72—I2	121.1 (6)
C27B—C26B—C25B	107 (2)	C73—C72—C71	117.6 (8)
C27B—C26B—H26C	110.3	F2—C73—C72	119.0 (7)
C27B—C26B—H26D	110.3	F2—C73—C74	119.0 (7)
C26B—C27B—H27C	111.2	C72—C73—C74	122.0 (8)
C26B—C27B—H27D	111.2	C73—C74—I3	119.7 (6)
C26B—C27B—C28	102.8 (14)	C75—C74—I3	122.4 (6)
H27C—C27B—H27D	109.1	C75—C74—C73	117.8 (7)
C28—C27B—H27C	111.2	F3—C75—C70	118.2 (7)
C28—C27B—H27D	111.2	F3—C75—C74	118.8 (7)
N4—C28—C27	113.6 (7)	C74—C75—C70	122.9 (8)
N4—C28—C27B	113.6 (7)	C77—C76—I4	121.3 (6)
N4—C28—H28A	108.8	C81—C76—I4	121.3 (6)
N4—C28—H28B	108.8	C81—C76—C77	117.3 (7)
C27—C28—H28A	108.8	F4—C77—C76	119.4 (7)
C27—C28—H28B	108.8	F4—C77—C78	118.7 (7)
H28A—C28—H28B	107.7	C76—C77—C78	121.9 (7)
C30—C29—N3	117.4 (8)	C77—C78—I5	120.7 (6)
C34—C29—N3	118.9 (9)	C79—C78—I5	121.5 (6)
C34—C29—C30	123.5 (9)	C79—C78—C77	117.8 (7)
C29—C30—C35	122.4 (8)	F5—C79—C78	118.7 (7)
C31—C30—C29	117.8 (10)	F5—C79—C80	118.3 (7)
C31—C30—C35	119.8 (10)	C78—C79—C80	122.9 (7)
C30—C31—H31	118.9	C79—C80—I6	120.8 (5)
C32—C31—C30	122.1 (12)	C79—C80—C81	116.8 (7)
C32—C31—H31	118.9	C81—C80—I6	122.4 (6)
C31—C32—C33	118.6 (10)	F6—C81—C76	119.7 (7)
C31—C32—C36	123.2 (12)	F6—C81—C80	117.0 (7)
C33—C32—C36	118.2 (12)	C76—C81—C80	123.2 (7)
C32—C33—H33	118.6	C83—C82—I7	121.3 (6)
C32—C33—C34	122.8 (11)	C83—C82—C87	117.1 (7)
C34—C33—H33	118.6	C87—C82—I7	120.9 (6)
C29—C34—C33	115.1 (11)	F7—C83—C82	117.8 (7)
C29—C34—C37	122.3 (10)	F7—C83—C84	118.6 (8)
C33—C34—C37	122.6 (10)	C84—C83—C82	123.6 (8)
C30—C35—H35A	109.5	C83—C84—I8	122.2 (6)
C30—C35—H35B	109.5	C83—C84—C85	116.8 (8)
C30—C35—H35C	109.5	C85—C84—I8	120.9 (6)
H35A—C35—H35B	109.5	F8—C85—C84	118.8 (8)
H35A—C35—H35C	109.5	F8—C85—C86	118.8 (7)
H35B—C35—H35C	109.5	C86—C85—C84	122.3 (8)
C32—C36—H36A	109.5	C85—C86—I9	120.1 (6)
C32—C36—H36B	109.5	C85—C86—C87	118.7 (7)
C32—C36—H36C	109.5	C87—C86—I9	121.0 (6)
H36A—C36—H36B	109.5	F9—C87—C82	118.5 (7)
H36A—C36—H36C	109.5	F9—C87—C86	119.9 (7)
H36B—C36—H36C	109.5	C86—C87—C82	121.5 (8)
I1—C70—C71—F1	8.9 (10)	C25B—N3—C24—S2	138.0 (14)
I1—C70—C71—C72	−169.8 (6)	C25B—N3—C24—N4	−42.5 (16)
I1—C70—C75—F3	−8.6 (11)	C25B—N3—C29—C30	118.6 (19)
I1—C70—C75—C74	168.4 (6)	C25B—N3—C29—C34	−57 (2)
I2—C72—C73—F2	−0.5 (11)	C25B—C26B—C27B—C28	70 (2)
I2—C72—C73—C74	−179.8 (6)	C26B—C27B—C28—N4	−86.0 (17)
I3—C74—C75—F3	1.0 (11)	C28—N4—C24—S2	157.6 (6)
I3—C74—C75—C70	−176.0 (6)	C28—N4—C24—N3	−21.9 (11)
I4—C76—C77—F4	−3.6 (11)	C28—N4—C38—C39	102.6 (9)
I4—C76—C77—C78	175.2 (6)	C28—N4—C38—C43	−67.7 (10)
I4—C76—C81—F6	4.5 (10)	C29—N3—C24—S2	−22.1 (10)
I4—C76—C81—C80	−175.3 (6)	C29—N3—C24—N4	157.3 (7)
I5—C78—C79—F5	3.0 (10)	C29—N3—C25—C26	158.6 (9)
I5—C78—C79—C80	−175.9 (6)	C29—N3—C25B—C26B	−113 (2)
I6—C80—C81—F6	−0.9 (10)	C29—C30—C31—C32	−1.1 (14)
I6—C80—C81—C76	178.9 (6)	C30—C29—C34—C33	2.0 (13)
I7—C82—C83—F7	9.1 (10)	C30—C29—C34—C37	−178.8 (9)
I7—C82—C83—C84	−170.4 (6)	C30—C31—C32—C33	2.7 (16)
I7—C82—C87—F9	−7.3 (11)	C30—C31—C32—C36	−174.7 (10)
I7—C82—C87—C86	168.2 (6)	C31—C32—C33—C34	−2.0 (15)
I8—C84—C85—F8	−0.2 (10)	C32—C33—C34—C29	−0.2 (14)
I8—C84—C85—C86	−178.4 (6)	C32—C33—C34—C37	−179.5 (10)
I9—C86—C87—F9	3.9 (11)	C34—C29—C30—C31	−1.3 (14)
I9—C86—C87—C82	−171.4 (6)	C34—C29—C30—C35	177.6 (9)
F1—C71—C72—I2	0.0 (11)	C35—C30—C31—C32	179.9 (9)
F1—C71—C72—C73	−178.8 (7)	C36—C32—C33—C34	175.6 (9)
F2—C73—C74—I3	−1.0 (11)	C38—N4—C24—S2	−9.7 (10)
F2—C73—C74—C75	−179.5 (7)	C38—N4—C24—N3	170.9 (7)
F4—C77—C78—I5	−3.9 (10)	C38—N4—C28—C27	−107.9 (9)
F4—C77—C78—C79	178.7 (7)	C38—N4—C28—C27B	−107.9 (9)
F5—C79—C80—I6	0.9 (10)	C38—C39—C40—C41	0.5 (13)
F5—C79—C80—C81	179.3 (7)	C39—C38—C43—C42	−0.6 (13)
F7—C83—C84—I8	−0.6 (10)	C39—C38—C43—C46	179.5 (8)
F7—C83—C84—C85	−177.7 (7)	C39—C40—C41—C42	−1.6 (13)
F8—C85—C86—I9	−4.9 (11)	C39—C40—C41—C45	175.7 (8)
F8—C85—C86—C87	−179.0 (7)	C40—C41—C42—C43	1.5 (12)
N1—C2—C3—C4	−79.3 (10)	C41—C42—C43—C38	−0.5 (13)
N1—C6—C7—C8	−174.5 (7)	C41—C42—C43—C46	179.5 (8)
N1—C6—C7—C12	7.5 (12)	C43—C38—C39—C40	0.6 (12)
N1—C6—C11—C10	175.3 (7)	C43—C38—C39—C44	−178.3 (8)
N1—C6—C11—C14	−8.1 (11)	C44—C39—C40—C41	179.5 (8)
N2—C15—C16—C17	−174.4 (7)	C45—C41—C42—C43	−175.8 (8)
N2—C15—C16—C21	9.8 (12)	C47—N5—C48—C49	87.1 (9)
N2—C15—C20—C19	175.0 (7)	C47—N5—C52—C53	−80.4 (10)
N2—C15—C20—C23	−4.8 (13)	C47—N5—C52—C57	103.8 (9)
N3—C25—C26—C27	76.8 (12)	C47—N6—C51—C50	−24.6 (12)
N3—C25B—C26B—C27B	−87 (3)	C47—N6—C61—C62	−85.0 (9)
N3—C29—C30—C31	−177.2 (8)	C47—N6—C61—C66	97.6 (9)
N3—C29—C30—C35	1.8 (13)	C48—N5—C47—S3	155.5 (6)
N3—C29—C34—C33	177.8 (8)	C48—N5—C47—N6	−21.7 (11)
N3—C29—C34—C37	−3.0 (14)	C48—N5—C52—C53	109.6 (9)
N4—C38—C39—C40	−169.3 (7)	C48—N5—C52—C57	−66.2 (10)
N4—C38—C39—C44	11.8 (12)	C48—C49—C50—C51	−36.0 (10)
N4—C38—C43—C42	169.3 (7)	C49—C50—C51—N6	79.1 (9)
N4—C38—C43—C46	−10.6 (12)	C51—N6—C47—S3	164.5 (6)
N5—C48—C49—C50	−49.9 (10)	C51—N6—C47—N5	−18.3 (12)
N5—C52—C53—C54	−175.0 (7)	C51—N6—C61—C62	97.0 (8)
N5—C52—C53—C58	4.3 (12)	C51—N6—C61—C66	−80.4 (9)
N5—C52—C57—C56	174.7 (7)	C52—N5—C47—S3	−13.9 (10)
N5—C52—C57—C60	−6.0 (12)	C52—N5—C47—N6	169.0 (7)
N6—C61—C62—C63	179.0 (7)	C52—N5—C48—C49	−103.0 (8)
N6—C61—C62—C67	−0.1 (11)	C52—C53—C54—C55	1.5 (12)
N6—C61—C66—C65	−179.3 (7)	C53—C52—C57—C56	−1.1 (12)
N6—C61—C66—C69	1.5 (11)	C53—C52—C57—C60	178.3 (8)
C1—N1—C2—C3	21.6 (12)	C53—C54—C55—C56	−2.9 (13)
C1—N1—C6—C7	−103.0 (9)	C53—C54—C55—C59	177.7 (8)
C1—N1—C6—C11	80.8 (9)	C54—C55—C56—C57	2.3 (13)
C1—N2—C5—C4	−85.5 (10)	C55—C56—C57—C52	−0.4 (13)
C1—N2—C15—C16	−102.8 (10)	C55—C56—C57—C60	−179.8 (8)
C1—N2—C15—C20	81.5 (11)	C57—C52—C53—C54	0.5 (12)
C2—N1—C1—S1	−156.1 (7)	C57—C52—C53—C58	179.9 (8)
C2—N1—C1—N2	25.9 (12)	C58—C53—C54—C55	−177.9 (9)
C2—N1—C6—C7	71.6 (9)	C59—C55—C56—C57	−178.2 (8)
C2—N1—C6—C11	−104.6 (8)	C61—N6—C47—S3	−13.2 (10)
C2—C3—C4—C5	36.4 (11)	C61—N6—C47—N5	164.0 (7)
C3—C4—C5—N2	51.2 (11)	C61—N6—C51—C50	153.2 (7)
C5—N2—C1—S1	−162.7 (7)	C61—C62—C63—C64	0.3 (12)
C5—N2—C1—N1	15.3 (12)	C62—C61—C66—C65	3.4 (12)
C5—N2—C15—C16	69.7 (10)	C62—C61—C66—C69	−175.8 (7)
C5—N2—C15—C20	−105.9 (10)	C62—C63—C64—C65	3.2 (13)
C6—N1—C1—S1	17.7 (10)	C62—C63—C64—C68	−173.8 (8)
C6—N1—C1—N2	−160.3 (7)	C63—C64—C65—C66	−3.5 (13)
C6—N1—C2—C3	−152.5 (8)	C64—C65—C66—C61	0.2 (12)
C6—C7—C8—C9	−1.0 (13)	C64—C65—C66—C69	179.4 (8)
C7—C6—C11—C10	−1.0 (11)	C66—C61—C62—C63	−3.7 (12)
C7—C6—C11—C14	175.7 (7)	C66—C61—C62—C67	177.2 (7)
C7—C8—C9—C10	−0.5 (14)	C67—C62—C63—C64	179.4 (8)
C7—C8—C9—C13	178.2 (9)	C68—C64—C65—C66	173.5 (8)
C8—C9—C10—C11	1.2 (13)	C70—C71—C72—I2	178.7 (6)
C9—C10—C11—C6	−0.5 (12)	C70—C71—C72—C73	−0.1 (13)
C9—C10—C11—C14	−177.2 (8)	C71—C70—C75—F3	179.6 (7)
C11—C6—C7—C8	1.7 (12)	C71—C70—C75—C74	−3.4 (12)
C11—C6—C7—C12	−176.4 (8)	C71—C72—C73—F2	178.3 (7)
C12—C7—C8—C9	177.1 (9)	C71—C72—C73—C74	−1.0 (13)
C13—C9—C10—C11	−177.5 (8)	C72—C73—C74—I3	178.4 (6)
C15—N2—C1—S1	9.4 (11)	C72—C73—C74—C75	−0.1 (13)
C15—N2—C1—N1	−172.6 (7)	C73—C74—C75—F3	179.4 (7)
C15—N2—C5—C4	101.9 (9)	C73—C74—C75—C70	2.4 (13)
C15—C16—C17—C18	−1.0 (13)	C75—C70—C71—F1	−179.1 (7)
C16—C15—C20—C19	−0.3 (13)	C75—C70—C71—C72	2.2 (12)
C16—C15—C20—C23	179.9 (9)	C76—C77—C78—I5	177.4 (6)
C16—C17—C18—C19	0.0 (14)	C76—C77—C78—C79	−0.1 (12)
C16—C17—C18—C22	−179.3 (9)	C77—C76—C81—F6	−179.3 (7)
C17—C18—C19—C20	0.9 (14)	C77—C76—C81—C80	0.9 (12)
C18—C19—C20—C15	−0.7 (13)	C77—C78—C79—F5	−179.5 (7)
C18—C19—C20—C23	179.1 (9)	C77—C78—C79—C80	1.5 (12)
C20—C15—C16—C17	1.1 (13)	C78—C79—C80—I6	179.8 (6)
C20—C15—C16—C21	−174.7 (9)	C78—C79—C80—C81	−1.7 (12)
C21—C16—C17—C18	174.9 (9)	C79—C80—C81—F6	−179.4 (7)
C22—C18—C19—C20	−179.8 (8)	C79—C80—C81—C76	0.4 (12)
C24—N3—C25—C26	−23.1 (15)	C81—C76—C77—F4	−179.8 (7)
C24—N3—C25B—C26B	89 (3)	C81—C76—C77—C78	−1.0 (12)
C24—N3—C29—C30	−85.6 (10)	C82—C83—C84—I8	178.9 (6)
C24—N3—C29—C34	98.4 (10)	C82—C83—C84—C85	1.8 (12)
C24—N4—C28—C27	84.0 (10)	C83—C82—C87—F9	−177.6 (7)
C24—N4—C28—C27B	84.0 (10)	C83—C82—C87—C86	−2.1 (12)
C24—N4—C38—C39	−89.3 (9)	C83—C84—C85—F8	176.9 (7)
C24—N4—C38—C43	100.3 (9)	C83—C84—C85—C86	−1.3 (12)
C25—N3—C24—S2	159.9 (9)	C84—C85—C86—I9	173.3 (6)
C25—N3—C24—N4	−20.7 (14)	C84—C85—C86—C87	−0.8 (13)
C25—N3—C29—C30	92.9 (10)	C85—C86—C87—F9	178.0 (7)
C25—N3—C29—C34	−83.1 (10)	C85—C86—C87—C82	2.6 (13)
C25—C26—C27—C28	−40.2 (12)	C87—C82—C83—F7	179.4 (7)
C26—C27—C28—N4	−46.5 (11)	C87—C82—C83—C84	−0.1 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···I6^i	0.99	3.30	4.234 (9)	158
C4—H4A···S1^ii	0.99	2.88	3.548 (10)	125
C5—H5B···F6^i	0.99	2.58	3.365 (11)	136
C25—H25B···I5^iii	0.99	3.12	3.960 (13)	144
C26—H26B···I7^iii	0.99	3.13	3.854 (11)	131
C27—H27B···F3^iv	0.99	2.48	3.283 (11)	138
C25B—H25C···I7^iii	0.99	3.24	4.06 (3)	141
C26B—H26D···S2^iii	0.99	2.85	3.60 (3)	134
C50—H50A···I9^v	0.99	3.07	3.843 (9)	136
C51—H51B···I3	0.99	3.13	4.083 (9)	162

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x, y+1, z; (iii) x, y−1, z; (iv) x, −y+1/2, z+1/2; (v) −x+1, −y+1, −z+1.

(SDiazMesSe_135F3I3B)

Crystal data

C6F3I3·C23H30N2Se	F(000) = 1752
Mr = 923.21	Dx = 2.035 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.0412 (6) Å	Cell parameters from 9992 reflections
b = 30.070 (2) Å	θ = 2.6–28.3°
c = 12.4774 (10) Å	µ = 4.36 mm^−1
β = 92.632 (3)°	T = 100 K
V = 3013.8 (4) Å^3	Needle, yellow
Z = 4	0.19 × 0.06 × 0.05 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	5611 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.058
φ and ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −10→10
Tmin = 0.617, Tmax = 0.746	k = −39→39
42494 measured reflections	l = −16→16
6919 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.064	H-atom parameters constrained
S = 1.17	w = 1/[σ^2(Fo^2) + (0.0047P)^2 + 7.9038P] where P = (Fo^2 + 2Fc^2)/3
6919 reflections	(Δ/σ)max = 0.003
349 parameters	Δρmax = 0.78 e Å^−3
0 restraints	Δρmin = −0.75 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	−0.17755 (3)	0.62711 (2)	0.48791 (2)	0.02317 (7)
I2	−0.18766 (3)	0.62277 (2)	0.00323 (2)	0.02355 (7)
I3	0.14307 (4)	0.47426 (2)	0.25977 (2)	0.02466 (7)
Se1	0.65449 (5)	0.64381 (2)	0.74419 (3)	0.01385 (8)
F1	−0.2079 (3)	0.65835 (8)	0.24335 (19)	0.0232 (5)
F2	0.0183 (3)	0.53625 (8)	0.06653 (19)	0.0269 (6)
F3	0.0163 (3)	0.53832 (8)	0.44236 (19)	0.0247 (5)
N1	0.3959 (4)	0.70475 (10)	0.7039 (2)	0.0136 (6)
N2	0.3068 (4)	0.63260 (10)	0.7396 (3)	0.0125 (6)
C1	0.4316 (4)	0.66193 (12)	0.7290 (3)	0.0124 (7)
C2	0.2349 (5)	0.71781 (13)	0.6505 (3)	0.0160 (8)
H2A	0.197805	0.694039	0.599925	0.019*
H2B	0.251043	0.745239	0.608308	0.019*
C3	0.1008 (5)	0.72586 (13)	0.7294 (3)	0.0182 (8)
H3A	−0.007616	0.730133	0.689846	0.022*
H3B	0.126610	0.753274	0.770795	0.022*
C4	0.0892 (5)	0.68660 (12)	0.8060 (3)	0.0151 (8)
H4A	−0.024349	0.685548	0.833436	0.018*
H4B	0.168540	0.691203	0.867998	0.018*
C5	0.1268 (5)	0.64218 (12)	0.7533 (3)	0.0146 (8)
H5A	0.080150	0.618098	0.796895	0.017*
H5B	0.068272	0.641324	0.681758	0.017*
C6	0.5214 (5)	0.73908 (12)	0.7124 (3)	0.0143 (8)
C7	0.5645 (5)	0.75722 (12)	0.8131 (3)	0.0151 (8)
C8	0.6746 (5)	0.79303 (12)	0.8168 (3)	0.0176 (8)
H8	0.705616	0.805960	0.884283	0.021*
C9	0.7403 (5)	0.81034 (13)	0.7246 (4)	0.0206 (9)
C10	0.6965 (5)	0.79098 (12)	0.6267 (3)	0.0179 (8)
H10	0.742031	0.802528	0.563502	0.021*
C11	0.5875 (5)	0.75507 (12)	0.6183 (3)	0.0153 (8)
C12	0.4987 (5)	0.73935 (14)	0.9148 (3)	0.0201 (9)
H12A	0.568919	0.714632	0.940916	0.030*
H12B	0.384419	0.728776	0.901102	0.030*
H12C	0.499703	0.762942	0.969032	0.030*
C13	0.8559 (6)	0.84997 (14)	0.7310 (4)	0.0298 (11)
H13A	0.790230	0.877432	0.727201	0.045*
H13B	0.930306	0.849051	0.671014	0.045*
H13C	0.922027	0.849130	0.798917	0.045*
C14	0.5433 (5)	0.73405 (13)	0.5112 (3)	0.0208 (9)
H14A	0.451134	0.750494	0.475607	0.031*
H14B	0.509619	0.703098	0.521900	0.031*
H14C	0.640201	0.734874	0.466443	0.031*
C15	0.3425 (5)	0.58531 (12)	0.7413 (3)	0.0134 (7)
C16	0.3532 (5)	0.56334 (13)	0.6434 (3)	0.0171 (8)
C17	0.3866 (5)	0.51761 (13)	0.6470 (4)	0.0222 (9)
H17	0.395225	0.501658	0.581763	0.027*
C18	0.4075 (5)	0.49511 (13)	0.7440 (4)	0.0217 (9)
C19	0.3883 (5)	0.51818 (13)	0.8385 (3)	0.0204 (9)
H19	0.398288	0.502562	0.904642	0.024*
C20	0.3548 (5)	0.56360 (13)	0.8397 (3)	0.0170 (8)
C21	0.3376 (5)	0.58789 (14)	0.5385 (3)	0.0225 (9)
H21A	0.232075	0.604262	0.534095	0.034*
H21B	0.340030	0.566596	0.479150	0.034*
H21C	0.430340	0.608833	0.533870	0.034*
C22	0.4657 (5)	0.44759 (13)	0.7456 (4)	0.0296 (11)
H22A	0.587391	0.446794	0.754502	0.044*
H22B	0.430578	0.433098	0.677963	0.044*
H22C	0.417082	0.431895	0.805495	0.044*
C23	0.3383 (5)	0.58822 (14)	0.9444 (3)	0.0217 (9)
H23A	0.405978	0.615319	0.944197	0.033*
H23B	0.376850	0.569122	1.004191	0.033*
H23C	0.221403	0.596153	0.952777	0.033*
C24	−0.0919 (5)	0.59979 (14)	0.3464 (3)	0.0193 (8)
C25	−0.1281 (5)	0.61885 (13)	0.2468 (3)	0.0185 (8)
C26	−0.0944 (5)	0.59839 (13)	0.1521 (3)	0.0187 (8)
C27	−0.0156 (5)	0.55722 (14)	0.1581 (3)	0.0199 (8)
C28	0.0259 (5)	0.53636 (13)	0.2544 (3)	0.0188 (8)
C29	−0.0152 (5)	0.55843 (13)	0.3471 (3)	0.0193 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02103 (14)	0.03125 (15)	0.01689 (14)	0.00181 (12)	−0.00276 (10)	−0.00307 (11)
I2	0.02080 (14)	0.03341 (15)	0.01665 (14)	0.00223 (12)	0.00304 (10)	0.00603 (11)
I3	0.02288 (14)	0.01824 (13)	0.03268 (16)	−0.00378 (11)	−0.00046 (12)	0.00129 (11)
Se1	0.01091 (18)	0.01608 (18)	0.01451 (19)	−0.00019 (14)	−0.00011 (14)	0.00126 (15)
F1	0.0215 (13)	0.0249 (12)	0.0230 (13)	0.0050 (10)	−0.0016 (10)	0.0021 (10)
F2	0.0327 (14)	0.0293 (14)	0.0192 (13)	0.0007 (11)	0.0055 (11)	−0.0018 (10)
F3	0.0280 (14)	0.0269 (13)	0.0191 (13)	−0.0025 (11)	−0.0008 (10)	0.0072 (10)
N1	0.0121 (16)	0.0146 (15)	0.0140 (16)	−0.0019 (12)	0.0008 (12)	0.0033 (12)
N2	0.0098 (15)	0.0114 (15)	0.0162 (16)	0.0010 (12)	0.0007 (12)	−0.0023 (12)
C1	0.0119 (18)	0.0175 (18)	0.0074 (17)	−0.0027 (15)	−0.0025 (14)	−0.0017 (14)
C2	0.0121 (19)	0.0185 (19)	0.017 (2)	0.0000 (15)	−0.0029 (15)	0.0032 (16)
C3	0.0132 (19)	0.0198 (19)	0.022 (2)	0.0049 (16)	−0.0001 (16)	0.0016 (16)
C4	0.0129 (19)	0.0166 (18)	0.016 (2)	0.0002 (15)	0.0023 (15)	−0.0019 (15)
C5	0.0117 (18)	0.0171 (18)	0.0150 (19)	−0.0005 (15)	0.0015 (15)	0.0001 (15)
C6	0.0139 (19)	0.0105 (17)	0.018 (2)	0.0006 (14)	−0.0011 (15)	0.0021 (15)
C7	0.0118 (18)	0.0155 (18)	0.018 (2)	0.0010 (15)	−0.0001 (15)	−0.0002 (15)
C8	0.018 (2)	0.0151 (18)	0.019 (2)	0.0018 (16)	−0.0044 (16)	−0.0042 (16)
C9	0.016 (2)	0.0130 (18)	0.033 (2)	0.0008 (16)	−0.0045 (17)	0.0001 (17)
C10	0.019 (2)	0.0137 (18)	0.021 (2)	−0.0021 (16)	0.0038 (16)	0.0065 (16)
C11	0.0157 (19)	0.0141 (18)	0.016 (2)	0.0025 (15)	0.0009 (15)	0.0022 (15)
C12	0.022 (2)	0.026 (2)	0.0120 (19)	−0.0037 (17)	−0.0006 (16)	−0.0019 (16)
C13	0.030 (3)	0.022 (2)	0.037 (3)	−0.0129 (19)	−0.002 (2)	−0.001 (2)
C14	0.022 (2)	0.022 (2)	0.019 (2)	−0.0069 (17)	0.0032 (17)	−0.0005 (16)
C15	0.0108 (18)	0.0122 (17)	0.0173 (19)	−0.0018 (14)	0.0024 (14)	0.0013 (15)
C16	0.0099 (18)	0.020 (2)	0.021 (2)	−0.0012 (15)	0.0037 (15)	−0.0039 (16)
C17	0.016 (2)	0.019 (2)	0.032 (2)	−0.0027 (16)	0.0021 (17)	−0.0092 (18)
C18	0.0097 (19)	0.0121 (18)	0.043 (3)	−0.0026 (15)	0.0020 (17)	−0.0006 (18)
C19	0.015 (2)	0.020 (2)	0.026 (2)	−0.0008 (16)	−0.0013 (16)	0.0080 (17)
C20	0.0116 (19)	0.0170 (19)	0.023 (2)	−0.0015 (15)	0.0031 (15)	0.0017 (16)
C21	0.022 (2)	0.027 (2)	0.019 (2)	−0.0026 (18)	0.0010 (17)	−0.0012 (17)
C22	0.017 (2)	0.016 (2)	0.056 (3)	−0.0016 (17)	0.002 (2)	0.005 (2)
C23	0.022 (2)	0.027 (2)	0.016 (2)	−0.0011 (18)	0.0008 (16)	0.0022 (17)
C24	0.016 (2)	0.026 (2)	0.016 (2)	−0.0047 (16)	−0.0016 (16)	−0.0057 (16)
C25	0.0111 (18)	0.022 (2)	0.022 (2)	−0.0007 (16)	0.0014 (15)	0.0001 (17)
C26	0.016 (2)	0.024 (2)	0.016 (2)	−0.0027 (16)	0.0004 (16)	0.0038 (16)
C27	0.016 (2)	0.025 (2)	0.019 (2)	−0.0030 (17)	0.0038 (16)	−0.0015 (17)
C28	0.019 (2)	0.0172 (19)	0.020 (2)	−0.0043 (16)	−0.0013 (16)	0.0018 (16)
C29	0.016 (2)	0.022 (2)	0.020 (2)	−0.0062 (16)	−0.0024 (16)	0.0048 (16)

Geometric parameters (Å, º)

I1—C24	2.092 (4)	C12—H12A	0.9800
I2—C26	2.103 (4)	C12—H12B	0.9800
I3—C28	2.091 (4)	C12—H12C	0.9800
Se1—C1	1.874 (4)	C13—H13A	0.9800
F1—C25	1.350 (4)	C13—H13B	0.9800
F2—C27	1.344 (5)	C13—H13C	0.9800
F3—C29	1.347 (4)	C14—H14A	0.9800
N1—C1	1.353 (5)	C14—H14B	0.9800
N1—C2	1.482 (5)	C14—H14C	0.9800
N1—C6	1.444 (5)	C15—C16	1.395 (5)
N2—C1	1.348 (5)	C15—C20	1.390 (5)
N2—C5	1.493 (5)	C16—C17	1.401 (5)
N2—C15	1.451 (4)	C16—C21	1.503 (6)
C2—H2A	0.9900	C17—H17	0.9500
C2—H2B	0.9900	C17—C18	1.389 (6)
C2—C3	1.513 (5)	C18—C19	1.383 (6)
C3—H3A	0.9900	C18—C22	1.504 (5)
C3—H3B	0.9900	C19—H19	0.9500
C3—C4	1.525 (5)	C19—C20	1.392 (5)
C4—H4A	0.9900	C20—C23	1.514 (6)
C4—H4B	0.9900	C21—H21A	0.9800
C4—C5	1.525 (5)	C21—H21B	0.9800
C5—H5A	0.9900	C21—H21C	0.9800
C5—H5B	0.9900	C22—H22A	0.9800
C6—C7	1.398 (5)	C22—H22B	0.9800
C6—C11	1.396 (5)	C22—H22C	0.9800
C7—C8	1.394 (5)	C23—H23A	0.9800
C7—C12	1.497 (5)	C23—H23B	0.9800
C8—H8	0.9500	C23—H23C	0.9800
C8—C9	1.389 (6)	C24—C25	1.387 (6)
C9—C10	1.385 (6)	C24—C29	1.388 (6)
C9—C13	1.511 (5)	C25—C26	1.370 (6)
C10—H10	0.9500	C26—C27	1.391 (6)
C10—C11	1.392 (5)	C27—C28	1.382 (6)
C11—C14	1.506 (5)	C28—C29	1.387 (6)
C1—N1—C2	121.9 (3)	H13B—C13—H13C	109.5
C1—N1—C6	121.5 (3)	C11—C14—H14A	109.5
C6—N1—C2	115.9 (3)	C11—C14—H14B	109.5
C1—N2—C5	128.0 (3)	C11—C14—H14C	109.5
C1—N2—C15	119.7 (3)	H14A—C14—H14B	109.5
C15—N2—C5	112.3 (3)	H14A—C14—H14C	109.5
N1—C1—Se1	119.5 (3)	H14B—C14—H14C	109.5
N2—C1—Se1	120.9 (3)	C16—C15—N2	118.2 (3)
N2—C1—N1	119.6 (3)	C20—C15—N2	118.6 (3)
N1—C2—H2A	109.1	C20—C15—C16	123.1 (4)
N1—C2—H2B	109.1	C15—C16—C17	117.2 (4)
N1—C2—C3	112.6 (3)	C15—C16—C21	121.6 (4)
H2A—C2—H2B	107.8	C17—C16—C21	121.2 (4)
C3—C2—H2A	109.1	C16—C17—H17	119.3
C3—C2—H2B	109.1	C18—C17—C16	121.4 (4)
C2—C3—H3A	109.5	C18—C17—H17	119.3
C2—C3—H3B	109.5	C17—C18—C22	120.0 (4)
C2—C3—C4	110.5 (3)	C19—C18—C17	119.0 (4)
H3A—C3—H3B	108.1	C19—C18—C22	120.8 (4)
C4—C3—H3A	109.5	C18—C19—H19	119.0
C4—C3—H3B	109.5	C18—C19—C20	122.0 (4)
C3—C4—H4A	109.0	C20—C19—H19	119.0
C3—C4—H4B	109.0	C15—C20—C19	117.2 (4)
C3—C4—C5	112.9 (3)	C15—C20—C23	121.8 (3)
H4A—C4—H4B	107.8	C19—C20—C23	120.9 (4)
C5—C4—H4A	109.0	C16—C21—H21A	109.5
C5—C4—H4B	109.0	C16—C21—H21B	109.5
N2—C5—C4	115.5 (3)	C16—C21—H21C	109.5
N2—C5—H5A	108.4	H21A—C21—H21B	109.5
N2—C5—H5B	108.4	H21A—C21—H21C	109.5
C4—C5—H5A	108.4	H21B—C21—H21C	109.5
C4—C5—H5B	108.4	C18—C22—H22A	109.5
H5A—C5—H5B	107.5	C18—C22—H22B	109.5
C7—C6—N1	119.2 (3)	C18—C22—H22C	109.5
C11—C6—N1	118.4 (3)	H22A—C22—H22B	109.5
C11—C6—C7	122.2 (3)	H22A—C22—H22C	109.5
C6—C7—C12	122.6 (3)	H22B—C22—H22C	109.5
C8—C7—C6	117.6 (4)	C20—C23—H23A	109.5
C8—C7—C12	119.8 (4)	C20—C23—H23B	109.5
C7—C8—H8	119.1	C20—C23—H23C	109.5
C9—C8—C7	121.8 (4)	H23A—C23—H23B	109.5
C9—C8—H8	119.1	H23A—C23—H23C	109.5
C8—C9—C13	120.5 (4)	H23B—C23—H23C	109.5
C10—C9—C8	118.9 (4)	C25—C24—I1	122.0 (3)
C10—C9—C13	120.6 (4)	C25—C24—C29	116.8 (4)
C9—C10—H10	119.1	C29—C24—I1	120.7 (3)
C9—C10—C11	121.8 (4)	F1—C25—C24	118.2 (4)
C11—C10—H10	119.1	F1—C25—C26	118.7 (4)
C6—C11—C14	121.2 (3)	C26—C25—C24	123.1 (4)
C10—C11—C6	117.8 (4)	C25—C26—I2	121.9 (3)
C10—C11—C14	121.0 (4)	C25—C26—C27	117.4 (4)
C7—C12—H12A	109.5	C27—C26—I2	120.1 (3)
C7—C12—H12B	109.5	F2—C27—C26	118.8 (4)
C7—C12—H12C	109.5	F2—C27—C28	118.4 (4)
H12A—C12—H12B	109.5	C28—C27—C26	122.8 (4)
H12A—C12—H12C	109.5	C27—C28—I3	121.6 (3)
H12B—C12—H12C	109.5	C27—C28—C29	116.8 (4)
C9—C13—H13A	109.5	C29—C28—I3	121.6 (3)
C9—C13—H13B	109.5	F3—C29—C24	118.2 (4)
C9—C13—H13C	109.5	F3—C29—C28	118.6 (4)
H13A—C13—H13B	109.5	C28—C29—C24	123.1 (4)
H13A—C13—H13C	109.5
I1—C24—C25—F1	6.2 (5)	C6—C7—C8—C9	−0.1 (6)
I1—C24—C25—C26	−170.3 (3)	C7—C6—C11—C10	−1.6 (6)
I1—C24—C29—F3	−6.1 (5)	C7—C6—C11—C14	178.1 (4)
I1—C24—C29—C28	172.0 (3)	C7—C8—C9—C10	−0.9 (6)
I2—C26—C27—F2	8.3 (5)	C7—C8—C9—C13	178.4 (4)
I2—C26—C27—C28	−170.0 (3)	C8—C9—C10—C11	0.6 (6)
I3—C28—C29—F3	−2.4 (5)	C9—C10—C11—C6	0.6 (6)
I3—C28—C29—C24	179.5 (3)	C9—C10—C11—C14	−179.1 (4)
F1—C25—C26—I2	−7.4 (5)	C11—C6—C7—C8	1.4 (6)
F1—C25—C26—C27	−178.5 (3)	C11—C6—C7—C12	−177.9 (4)
F2—C27—C28—I3	1.2 (5)	C12—C7—C8—C9	179.2 (4)
F2—C27—C28—C29	−178.2 (3)	C13—C9—C10—C11	−178.6 (4)
N1—C2—C3—C4	−51.0 (4)	C15—N2—C1—Se1	−12.4 (5)
N1—C6—C7—C8	−174.2 (3)	C15—N2—C1—N1	165.5 (3)
N1—C6—C7—C12	6.5 (5)	C15—N2—C5—C4	151.2 (3)
N1—C6—C11—C10	174.0 (3)	C15—C16—C17—C18	0.3 (6)
N1—C6—C11—C14	−6.3 (5)	C16—C15—C20—C19	3.5 (6)
N2—C15—C16—C17	−179.5 (3)	C16—C15—C20—C23	−178.4 (4)
N2—C15—C16—C21	3.2 (5)	C16—C17—C18—C19	2.5 (6)
N2—C15—C20—C19	179.7 (3)	C16—C17—C18—C22	−171.8 (4)
N2—C15—C20—C23	−2.3 (5)	C17—C18—C19—C20	−2.4 (6)
C1—N1—C2—C3	86.2 (4)	C18—C19—C20—C15	−0.5 (6)
C1—N1—C6—C7	−79.6 (5)	C18—C19—C20—C23	−178.6 (4)
C1—N1—C6—C11	104.6 (4)	C20—C15—C16—C17	−3.4 (6)
C1—N2—C5—C4	−27.2 (5)	C20—C15—C16—C21	179.3 (4)
C1—N2—C15—C16	−83.6 (4)	C21—C16—C17—C18	177.5 (4)
C1—N2—C15—C20	100.1 (4)	C22—C18—C19—C20	171.9 (4)
C2—N1—C1—Se1	155.8 (3)	C24—C25—C26—I2	169.1 (3)
C2—N1—C1—N2	−22.2 (5)	C24—C25—C26—C27	−2.0 (6)
C2—N1—C6—C7	109.6 (4)	C25—C24—C29—F3	−177.7 (3)
C2—N1—C6—C11	−66.2 (4)	C25—C24—C29—C28	0.4 (6)
C2—C3—C4—C5	−33.6 (4)	C25—C26—C27—F2	179.7 (3)
C3—C4—C5—N2	77.7 (4)	C25—C26—C27—C28	1.3 (6)
C5—N2—C1—Se1	165.9 (3)	C26—C27—C28—I3	179.6 (3)
C5—N2—C1—N1	−16.2 (6)	C26—C27—C28—C29	0.2 (6)
C5—N2—C15—C16	97.8 (4)	C27—C28—C29—F3	177.0 (3)
C5—N2—C15—C20	−78.5 (4)	C27—C28—C29—C24	−1.0 (6)
C6—N1—C1—Se1	−14.5 (5)	C29—C24—C25—F1	177.7 (3)
C6—N1—C1—N2	167.6 (3)	C29—C24—C25—C26	1.2 (6)
C6—N1—C2—C3	−103.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···I2^i	0.99	3.17	3.899 (4)	132
C4—H4A···Se1^ii	0.99	3.04	3.771 (4)	132
C5—H5B···I1	0.99	3.08	4.051 (4)	167

Symmetry codes: (i) x, y, z+1; (ii) x−1, y, z.

(SDiazMesS_IF5B)

Crystal data

C6F5I·C23H30N2S	Dx = 1.586 Mg m^−3
Mr = 660.51	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 9953 reflections
a = 7.8472 (5) Å	θ = 2.5–27.6°
b = 16.1751 (13) Å	µ = 1.29 mm^−1
c = 21.7956 (19) Å	T = 100 K
V = 2766.5 (4) Å^3	Plate, colourless
Z = 4	0.41 × 0.06 × 0.03 mm
F(000) = 1328

Data collection

Bruker D8 Venture Photon 2 diffractometer	5489 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.048
φ and ω scans	θmax = 27.6°, θmin = 2.5°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −9→10
Tmin = 0.632, Tmax = 0.746	k = −20→21
30210 measured reflections	l = −25→28
6227 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.028	H-atom parameters constrained
wR(F^2) = 0.063	w = 1/[σ^2(Fo^2) + (0.0101P)^2 + 2.3147P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max = 0.001
6227 reflections	Δρmax = 0.68 e Å^−3
349 parameters	Δρmin = −0.52 e Å^−3
1 restraint	Absolute structure: Flack x determined using 2370 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Primary atom site location: dual	Absolute structure parameter: −0.027 (12)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.74559 (4)	0.38135 (2)	0.45841 (3)	0.02119 (7)
S1	0.55819 (14)	0.43685 (7)	0.58109 (6)	0.0190 (2)
F5	0.8291 (4)	0.20019 (17)	0.40434 (14)	0.0278 (6)
F1	0.9675 (4)	0.47782 (18)	0.35709 (16)	0.0327 (7)
F4	1.0107 (4)	0.14996 (19)	0.30642 (16)	0.0382 (8)
F3	1.1763 (4)	0.2619 (2)	0.23501 (15)	0.0436 (9)
F2	1.1586 (4)	0.4262 (2)	0.26231 (16)	0.0416 (8)
C24	0.8934 (6)	0.3402 (3)	0.3843 (2)	0.0197 (10)
N1	0.2654 (4)	0.4634 (2)	0.63795 (18)	0.0155 (7)
N2	0.3299 (5)	0.5555 (2)	0.55822 (18)	0.0188 (8)
C29	0.9084 (6)	0.2576 (3)	0.3701 (2)	0.0225 (10)
C1	0.3716 (5)	0.4880 (3)	0.5925 (2)	0.0161 (9)
C16	0.5720 (6)	0.6494 (3)	0.5473 (2)	0.0189 (9)
C8	0.4076 (6)	0.3122 (3)	0.7562 (2)	0.0195 (9)
H8	0.467307	0.312016	0.794072	0.023*
C7	0.3822 (6)	0.3868 (3)	0.7254 (2)	0.0172 (9)
C14	0.1405 (6)	0.3103 (3)	0.5832 (2)	0.0246 (10)
H14A	0.043521	0.348407	0.584364	0.037*
H14B	0.099434	0.254039	0.575349	0.037*
H14C	0.218855	0.326878	0.550439	0.037*
C2	0.1371 (6)	0.5194 (3)	0.6648 (2)	0.0210 (10)
H2A	0.184634	0.576014	0.666911	0.025*
H2B	0.111153	0.501324	0.707201	0.025*
C17	0.6981 (6)	0.6843 (3)	0.5105 (2)	0.0208 (10)
H17	0.773411	0.723857	0.527897	0.025*
C9	0.3468 (6)	0.2379 (3)	0.7322 (2)	0.0190 (9)
C3	−0.0273 (6)	0.5208 (3)	0.6274 (3)	0.0280 (11)
H3A	−0.100430	0.566882	0.641493	0.034*
H3B	−0.090341	0.468460	0.633738	0.034*
C6	0.2955 (6)	0.3857 (3)	0.6695 (2)	0.0162 (9)
C19	0.6034 (6)	0.6061 (3)	0.4238 (2)	0.0202 (10)
H19	0.615091	0.591231	0.381837	0.024*
C20	0.4731 (5)	0.5708 (2)	0.4588 (3)	0.0193 (8)
C15	0.4610 (5)	0.5925 (3)	0.5203 (2)	0.0171 (9)
C18	0.7167 (5)	0.6631 (3)	0.4496 (3)	0.0210 (12)
C28	1.0015 (6)	0.2303 (3)	0.3199 (3)	0.0266 (11)
C10	0.2602 (5)	0.2391 (3)	0.6768 (2)	0.0164 (9)
H10	0.218096	0.188681	0.660407	0.020*
C13	0.3813 (6)	0.1576 (3)	0.7655 (2)	0.0245 (11)
H13A	0.504269	0.147125	0.766370	0.037*
H13B	0.323720	0.112186	0.744160	0.037*
H13C	0.338180	0.161414	0.807637	0.037*
C12	0.4550 (6)	0.4668 (3)	0.7507 (2)	0.0243 (10)
H12A	0.364726	0.497886	0.771573	0.036*
H12B	0.500856	0.500069	0.716925	0.036*
H12C	0.546284	0.454249	0.779912	0.036*
C4	0.0124 (6)	0.5315 (3)	0.5589 (2)	0.0263 (11)
H4A	0.042933	0.477165	0.541192	0.032*
H4B	−0.090939	0.551663	0.537573	0.032*
C23	0.3527 (7)	0.5092 (3)	0.4302 (2)	0.0253 (10)
H23A	0.249065	0.537778	0.416681	0.038*
H23B	0.322803	0.466828	0.460429	0.038*
H23C	0.407818	0.483123	0.394794	0.038*
C21	0.5576 (6)	0.6704 (3)	0.6147 (2)	0.0245 (11)
H21A	0.583976	0.621249	0.639284	0.037*
H21B	0.441391	0.688838	0.623799	0.037*
H21C	0.638269	0.714607	0.624832	0.037*
C22	0.8583 (7)	0.6993 (3)	0.4108 (3)	0.0303 (12)
H22A	0.901235	0.749839	0.430230	0.045*
H22B	0.814155	0.712561	0.369874	0.045*
H22C	0.951092	0.659103	0.407109	0.045*
C25	0.9780 (6)	0.3959 (3)	0.3466 (2)	0.0230 (10)
C5	0.1568 (6)	0.5916 (3)	0.5480 (3)	0.0272 (11)
H5A	0.149769	0.612139	0.505271	0.033*
H5B	0.142163	0.639676	0.575647	0.033*
C26	1.0746 (6)	0.3704 (3)	0.2971 (2)	0.0280 (11)
C27	1.0839 (6)	0.2877 (4)	0.2835 (2)	0.0300 (12)
C11	0.2333 (6)	0.3126 (3)	0.6446 (2)	0.0186 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01890 (12)	0.02310 (12)	0.02157 (13)	0.00241 (10)	−0.00039 (13)	−0.0020 (2)
S1	0.0156 (5)	0.0201 (5)	0.0214 (6)	0.0045 (4)	0.0026 (5)	0.0034 (5)
F5	0.0248 (15)	0.0227 (14)	0.0360 (18)	−0.0017 (12)	−0.0021 (13)	0.0028 (13)
F1	0.0319 (17)	0.0213 (15)	0.045 (2)	−0.0026 (12)	−0.0017 (15)	0.0050 (14)
F4	0.0340 (17)	0.0347 (17)	0.046 (2)	0.0082 (14)	−0.0058 (15)	−0.0181 (16)
F3	0.0303 (19)	0.076 (3)	0.0242 (18)	0.0101 (17)	0.0039 (15)	−0.0119 (17)
F2	0.0281 (18)	0.062 (2)	0.035 (2)	−0.0059 (15)	0.0029 (14)	0.0207 (17)
C24	0.014 (2)	0.023 (2)	0.022 (3)	0.0033 (17)	−0.0001 (17)	−0.0005 (19)
N1	0.0149 (18)	0.0152 (18)	0.016 (2)	0.0013 (14)	0.0010 (15)	0.0008 (15)
N2	0.0136 (19)	0.0206 (19)	0.022 (2)	0.0024 (14)	0.0024 (15)	0.0020 (16)
C29	0.017 (2)	0.025 (2)	0.025 (3)	0.0005 (18)	−0.0013 (19)	−0.001 (2)
C1	0.015 (2)	0.016 (2)	0.017 (2)	−0.0006 (16)	−0.0016 (16)	−0.0018 (17)
C16	0.020 (2)	0.016 (2)	0.021 (2)	0.0029 (17)	−0.0021 (18)	0.0011 (19)
C8	0.017 (2)	0.022 (2)	0.019 (2)	−0.0003 (17)	−0.0006 (18)	−0.0001 (19)
C7	0.015 (2)	0.016 (2)	0.020 (2)	−0.0006 (15)	0.0009 (17)	−0.0001 (18)
C14	0.028 (3)	0.024 (2)	0.022 (3)	−0.0039 (19)	−0.007 (2)	0.002 (2)
C2	0.016 (2)	0.021 (2)	0.026 (3)	0.0018 (17)	0.0044 (19)	0.0004 (19)
C17	0.023 (2)	0.015 (2)	0.025 (3)	−0.0016 (17)	−0.004 (2)	−0.002 (2)
C9	0.017 (2)	0.022 (2)	0.019 (2)	−0.0021 (17)	0.0047 (18)	0.0012 (19)
C3	0.016 (2)	0.034 (3)	0.034 (3)	0.003 (2)	0.002 (2)	0.003 (2)
C6	0.015 (2)	0.017 (2)	0.017 (2)	0.0004 (16)	0.0040 (17)	0.0012 (18)
C19	0.022 (2)	0.020 (2)	0.019 (3)	−0.0014 (17)	−0.0023 (18)	−0.0002 (18)
C20	0.0191 (19)	0.0172 (18)	0.022 (2)	0.0010 (14)	−0.004 (2)	0.003 (2)
C15	0.013 (2)	0.017 (2)	0.021 (2)	0.0012 (16)	−0.0004 (17)	0.0041 (18)
C18	0.018 (2)	0.0159 (19)	0.029 (4)	0.0002 (14)	0.000 (2)	0.004 (2)
C28	0.020 (2)	0.032 (3)	0.028 (3)	0.003 (2)	−0.0060 (19)	−0.008 (2)
C10	0.016 (2)	0.014 (2)	0.019 (2)	−0.0027 (16)	0.0019 (17)	−0.0006 (18)
C13	0.024 (3)	0.020 (2)	0.029 (3)	−0.0006 (19)	0.000 (2)	0.003 (2)
C12	0.026 (3)	0.020 (2)	0.026 (3)	−0.0018 (18)	−0.005 (2)	−0.004 (2)
C4	0.017 (2)	0.029 (3)	0.033 (3)	0.0018 (19)	−0.005 (2)	0.003 (2)
C23	0.027 (3)	0.023 (2)	0.026 (3)	−0.0051 (19)	−0.005 (2)	−0.002 (2)
C21	0.026 (3)	0.023 (2)	0.025 (3)	−0.0025 (19)	0.000 (2)	−0.005 (2)
C22	0.028 (3)	0.035 (3)	0.028 (3)	−0.009 (2)	0.002 (2)	0.003 (2)
C25	0.019 (2)	0.024 (2)	0.026 (3)	−0.0012 (18)	−0.0035 (19)	0.001 (2)
C5	0.019 (3)	0.028 (3)	0.034 (3)	0.0047 (19)	−0.005 (2)	0.003 (2)
C26	0.016 (2)	0.045 (3)	0.023 (3)	−0.001 (2)	−0.0005 (19)	0.007 (2)
C27	0.017 (2)	0.055 (4)	0.018 (3)	0.007 (2)	0.0018 (19)	−0.006 (2)
C11	0.017 (2)	0.018 (2)	0.020 (2)	−0.0047 (17)	−0.0020 (18)	−0.0005 (18)

Geometric parameters (Å, º)

I1—C24	2.097 (5)	C3—H3A	0.9900
S1—C1	1.700 (4)	C3—H3B	0.9900
F5—C29	1.343 (5)	C3—C4	1.534 (7)
F1—C25	1.347 (6)	C6—C11	1.391 (6)
F4—C28	1.333 (6)	C19—H19	0.9500
F3—C27	1.349 (6)	C19—C20	1.398 (7)
F2—C26	1.350 (6)	C19—C18	1.399 (6)
C24—C29	1.378 (6)	C20—C15	1.389 (8)
C24—C25	1.388 (7)	C20—C23	1.508 (6)
N1—C1	1.354 (6)	C18—C22	1.515 (7)
N1—C2	1.476 (6)	C28—C27	1.381 (8)
N1—C6	1.452 (6)	C10—H10	0.9500
N2—C1	1.363 (6)	C10—C11	1.397 (7)
N2—C15	1.450 (6)	C13—H13A	0.9800
N2—C5	1.495 (6)	C13—H13B	0.9800
C29—C28	1.389 (7)	C13—H13C	0.9800
C16—C17	1.392 (7)	C12—H12A	0.9800
C16—C15	1.397 (6)	C12—H12B	0.9800
C16—C21	1.514 (7)	C12—H12C	0.9800
C8—H8	0.9500	C4—H4A	0.9900
C8—C7	1.394 (6)	C4—H4B	0.9900
C8—C9	1.394 (6)	C4—C5	1.512 (7)
C7—C6	1.395 (7)	C23—H23A	0.9800
C7—C12	1.519 (6)	C23—H23B	0.9800
C14—H14A	0.9800	C23—H23C	0.9800
C14—H14B	0.9800	C21—H21A	0.9800
C14—H14C	0.9800	C21—H21B	0.9800
C14—C11	1.523 (7)	C21—H21C	0.9800
C2—H2A	0.9900	C22—H22A	0.9800
C2—H2B	0.9900	C22—H22B	0.9800
C2—C3	1.527 (7)	C22—H22C	0.9800
C17—H17	0.9500	C25—C26	1.381 (7)
C17—C18	1.379 (8)	C5—H5A	0.9900
C9—C10	1.386 (7)	C5—H5B	0.9900
C9—C13	1.512 (6)	C26—C27	1.372 (8)
C29—C24—I1	121.9 (4)	C19—C18—C22	119.8 (5)
C29—C24—C25	117.1 (4)	F4—C28—C29	120.7 (5)
C25—C24—I1	121.0 (3)	F4—C28—C27	120.3 (5)
C1—N1—C2	122.0 (4)	C27—C28—C29	119.0 (5)
C1—N1—C6	120.1 (4)	C9—C10—H10	119.2
C6—N1—C2	117.0 (4)	C9—C10—C11	121.7 (4)
C1—N2—C15	118.2 (4)	C11—C10—H10	119.2
C1—N2—C5	127.8 (4)	C9—C13—H13A	109.5
C15—N2—C5	113.5 (4)	C9—C13—H13B	109.5
F5—C29—C24	120.4 (4)	C9—C13—H13C	109.5
F5—C29—C28	117.5 (4)	H13A—C13—H13B	109.5
C24—C29—C28	122.1 (5)	H13A—C13—H13C	109.5
N1—C1—S1	119.6 (3)	H13B—C13—H13C	109.5
N1—C1—N2	119.3 (4)	C7—C12—H12A	109.5
N2—C1—S1	121.1 (3)	C7—C12—H12B	109.5
C17—C16—C15	117.9 (5)	C7—C12—H12C	109.5
C17—C16—C21	121.4 (4)	H12A—C12—H12B	109.5
C15—C16—C21	120.6 (4)	H12A—C12—H12C	109.5
C7—C8—H8	119.4	H12B—C12—H12C	109.5
C9—C8—H8	119.4	C3—C4—H4A	109.2
C9—C8—C7	121.2 (4)	C3—C4—H4B	109.2
C8—C7—C6	118.6 (4)	H4A—C4—H4B	107.9
C8—C7—C12	120.7 (4)	C5—C4—C3	112.2 (4)
C6—C7—C12	120.7 (4)	C5—C4—H4A	109.2
H14A—C14—H14B	109.5	C5—C4—H4B	109.2
H14A—C14—H14C	109.5	C20—C23—H23A	109.5
H14B—C14—H14C	109.5	C20—C23—H23B	109.5
C11—C14—H14A	109.5	C20—C23—H23C	109.5
C11—C14—H14B	109.5	H23A—C23—H23B	109.5
C11—C14—H14C	109.5	H23A—C23—H23C	109.5
N1—C2—H2A	109.2	H23B—C23—H23C	109.5
N1—C2—H2B	109.2	C16—C21—H21A	109.5
N1—C2—C3	111.9 (4)	C16—C21—H21B	109.5
H2A—C2—H2B	107.9	C16—C21—H21C	109.5
C3—C2—H2A	109.2	H21A—C21—H21B	109.5
C3—C2—H2B	109.2	H21A—C21—H21C	109.5
C16—C17—H17	119.0	H21B—C21—H21C	109.5
C18—C17—C16	121.9 (4)	C18—C22—H22A	109.5
C18—C17—H17	119.0	C18—C22—H22B	109.5
C8—C9—C13	120.0 (4)	C18—C22—H22C	109.5
C10—C9—C8	118.8 (4)	H22A—C22—H22B	109.5
C10—C9—C13	121.2 (4)	H22A—C22—H22C	109.5
C2—C3—H3A	109.6	H22B—C22—H22C	109.5
C2—C3—H3B	109.6	F1—C25—C24	120.5 (4)
C2—C3—C4	110.5 (4)	F1—C25—C26	117.3 (4)
H3A—C3—H3B	108.1	C26—C25—C24	122.1 (5)
C4—C3—H3A	109.6	N2—C5—C4	113.9 (4)
C4—C3—H3B	109.6	N2—C5—H5A	108.8
C7—C6—N1	118.8 (4)	N2—C5—H5B	108.8
C11—C6—N1	119.5 (4)	C4—C5—H5A	108.8
C11—C6—C7	121.6 (4)	C4—C5—H5B	108.8
C20—C19—H19	119.5	H5A—C5—H5B	107.7
C20—C19—C18	121.0 (5)	F2—C26—C25	120.5 (5)
C18—C19—H19	119.5	F2—C26—C27	120.3 (5)
C19—C20—C23	120.1 (5)	C27—C26—C25	119.2 (5)
C15—C20—C19	118.3 (4)	F3—C27—C28	119.5 (5)
C15—C20—C23	121.6 (4)	F3—C27—C26	120.0 (5)
C16—C15—N2	118.4 (4)	C26—C27—C28	120.5 (5)
C20—C15—N2	119.6 (4)	C6—C11—C14	122.2 (4)
C20—C15—C16	122.0 (4)	C6—C11—C10	118.2 (4)
C17—C18—C19	118.9 (5)	C10—C11—C14	119.6 (4)
C17—C18—C22	121.3 (4)
I1—C24—C29—F5	−0.9 (6)	C2—N1—C6—C7	−72.0 (5)
I1—C24—C29—C28	177.8 (4)	C2—N1—C6—C11	106.0 (5)
I1—C24—C25—F1	0.4 (6)	C2—C3—C4—C5	−39.2 (6)
I1—C24—C25—C26	−179.3 (4)	C17—C16—C15—N2	179.7 (4)
F5—C29—C28—F4	0.2 (7)	C17—C16—C15—C20	−0.3 (6)
F5—C29—C28—C27	179.7 (4)	C9—C8—C7—C6	−0.6 (7)
F1—C25—C26—F2	2.0 (7)	C9—C8—C7—C12	−177.6 (4)
F1—C25—C26—C27	−177.8 (4)	C9—C10—C11—C14	178.7 (4)
F4—C28—C27—F3	−1.2 (7)	C9—C10—C11—C6	−0.2 (7)
F4—C28—C27—C26	179.9 (4)	C3—C4—C5—N2	79.2 (5)
F2—C26—C27—F3	−0.5 (7)	C6—N1—C1—S1	−10.7 (6)
F2—C26—C27—C28	178.5 (5)	C6—N1—C1—N2	171.8 (4)
C24—C29—C28—F4	−178.5 (4)	C6—N1—C2—C3	−106.4 (5)
C24—C29—C28—C27	1.0 (8)	C19—C20—C15—N2	−178.5 (4)
C24—C25—C26—F2	−178.3 (5)	C19—C20—C15—C16	1.4 (6)
C24—C25—C26—C27	1.9 (8)	C20—C19—C18—C17	−0.1 (6)
N1—C2—C3—C4	−47.6 (6)	C20—C19—C18—C22	179.0 (4)
N1—C6—C11—C14	2.8 (7)	C15—N2—C1—S1	−11.9 (6)
N1—C6—C11—C10	−178.3 (4)	C15—N2—C1—N1	165.5 (4)
C29—C24—C25—F1	179.1 (4)	C15—N2—C5—C4	150.0 (4)
C29—C24—C25—C26	−0.6 (7)	C15—C16—C17—C18	−1.1 (7)
C29—C28—C27—F3	179.3 (4)	C18—C19—C20—C15	−1.2 (6)
C29—C28—C27—C26	0.3 (8)	C18—C19—C20—C23	−179.8 (4)
C1—N1—C2—C3	84.7 (5)	C13—C9—C10—C11	−177.6 (4)
C1—N1—C6—C7	97.1 (5)	C12—C7—C6—N1	−4.4 (6)
C1—N1—C6—C11	−84.9 (5)	C12—C7—C6—C11	177.7 (4)
C1—N2—C15—C16	−84.2 (5)	C23—C20—C15—N2	0.0 (6)
C1—N2—C15—C20	95.7 (5)	C23—C20—C15—C16	180.0 (4)
C1—N2—C5—C4	−21.9 (7)	C21—C16—C17—C18	177.3 (4)
C16—C17—C18—C19	1.3 (7)	C21—C16—C15—N2	1.3 (6)
C16—C17—C18—C22	−177.9 (5)	C21—C16—C15—C20	−178.7 (4)
C8—C7—C6—N1	178.7 (4)	C25—C24—C29—F5	−179.6 (4)
C8—C7—C6—C11	0.7 (7)	C25—C24—C29—C28	−0.9 (7)
C8—C9—C10—C11	0.3 (7)	C25—C26—C27—F3	179.3 (5)
C7—C8—C9—C10	0.1 (7)	C25—C26—C27—C28	−1.7 (8)
C7—C8—C9—C13	178.0 (4)	C5—N2—C1—S1	159.6 (4)
C7—C6—C11—C14	−179.2 (4)	C5—N2—C1—N1	−22.9 (7)
C7—C6—C11—C10	−0.3 (7)	C5—N2—C15—C16	103.0 (5)
C2—N1—C1—S1	157.8 (3)	C5—N2—C15—C20	−77.0 (5)
C2—N1—C1—N2	−19.7 (6)

(2SDiazMesSe_5F5IB)

Crystal data

5(C6F5I)·2(C23H30N2Se)	F(000) = 2204
Mr = 2296.70	Dx = 1.939 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 25.9292 (14) Å	Cell parameters from 9981 reflections
b = 8.0709 (4) Å	θ = 2.6–27.5°
c = 20.4309 (11) Å	µ = 3.01 mm^−1
β = 113.037 (2)°	T = 100 K
V = 3934.6 (4) Å^3	Plate, yellow
Z = 2	0.24 × 0.19 × 0.13 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	8222 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.035
φ and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −33→33
Tmin = 0.662, Tmax = 0.746	k = −10→10
61094 measured reflections	l = −26→26
9058 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.024	H-atom parameters constrained
wR(F^2) = 0.053	w = 1/[σ^2(Fo^2) + (0.0103P)^2 + 7.6201P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.002
9058 reflections	Δρmax = 1.06 e Å^−3
565 parameters	Δρmin = −0.75 e Å^−3
51 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
I1	0.36299 (2)	0.15544 (2)	−0.10920 (2)	0.02006 (4)
F1	0.48386 (7)	0.3203 (2)	−0.03476 (8)	0.0292 (3)
F2	0.56519 (7)	0.2949 (2)	0.09629 (9)	0.0344 (4)
F3	0.55311 (6)	0.0830 (2)	0.19303 (8)	0.0295 (3)
F4	0.46037 (6)	−0.10999 (18)	0.15628 (8)	0.0230 (3)
F5	0.37763 (6)	−0.08396 (18)	0.02570 (8)	0.0226 (3)
C24	0.42819 (10)	0.1194 (3)	−0.00858 (13)	0.0184 (5)
C25	0.47680 (11)	0.2123 (3)	0.01111 (14)	0.0211 (5)
C26	0.51903 (10)	0.2011 (3)	0.07825 (14)	0.0222 (5)
C27	0.51331 (10)	0.0921 (3)	0.12718 (13)	0.0214 (5)
C28	0.46566 (10)	−0.0048 (3)	0.10812 (13)	0.0184 (5)
C29	0.42379 (10)	0.0099 (3)	0.04130 (13)	0.0176 (5)
I2	0.82447 (2)	0.56411 (2)	0.71374 (2)	0.02300 (4)
F6	0.84760 (7)	0.4894 (3)	0.57197 (9)	0.0413 (5)
F7	0.93111 (9)	0.3325 (3)	0.55144 (10)	0.0498 (5)
F8	1.01570 (8)	0.1920 (2)	0.66196 (12)	0.0466 (5)
F9	1.01590 (8)	0.2089 (3)	0.79492 (11)	0.0490 (5)
F10	0.93198 (8)	0.3638 (2)	0.81645 (8)	0.0372 (4)
C30	0.88741 (10)	0.4339 (3)	0.69523 (13)	0.0183 (5)
C31	0.88868 (11)	0.4229 (3)	0.62860 (14)	0.0231 (5)
C32	0.93157 (12)	0.3434 (4)	0.61722 (15)	0.0279 (6)
C33	0.97452 (11)	0.2720 (3)	0.67329 (17)	0.0289 (6)
C34	0.97427 (11)	0.2807 (3)	0.74002 (16)	0.0290 (6)
C35	0.93099 (11)	0.3605 (3)	0.75041 (13)	0.0228 (5)
Se1	0.73177 (2)	0.76413 (3)	0.26819 (2)	0.01628 (5)
N1	0.68680 (8)	0.5035 (2)	0.31895 (11)	0.0167 (4)
N2	0.75425 (8)	0.4207 (2)	0.27638 (11)	0.0175 (4)
C1	0.72370 (10)	0.5418 (3)	0.28930 (12)	0.0154 (4)
C2	0.76653 (12)	0.2513 (3)	0.30925 (16)	0.0284 (6)
H2A	0.804787	0.219042	0.314519	0.034*
H2B	0.740053	0.171656	0.276056	0.034*
C3	0.76260 (13)	0.2353 (4)	0.38095 (17)	0.0337 (7)
H3A	0.780363	0.333056	0.410391	0.040*
H3B	0.783566	0.135636	0.405497	0.040*
C4	0.70207 (13)	0.2217 (4)	0.37435 (18)	0.0351 (7)
H4A	0.689292	0.105434	0.364189	0.042*
H4B	0.699832	0.254260	0.419890	0.042*
C5	0.66415 (11)	0.3331 (3)	0.31507 (15)	0.0250 (5)
H5A	0.659108	0.283550	0.268633	0.030*
H5B	0.626869	0.339055	0.317692	0.030*
C6	0.78182 (10)	0.4493 (3)	0.22777 (13)	0.0169 (5)
C7	0.83803 (10)	0.4949 (3)	0.25493 (14)	0.0198 (5)
C8	0.86397 (11)	0.5146 (3)	0.20695 (15)	0.0243 (5)
H8	0.902347	0.545733	0.224618	0.029*
C9	0.83560 (12)	0.4903 (3)	0.13458 (15)	0.0249 (5)
C10	0.77979 (12)	0.4396 (3)	0.10960 (14)	0.0250 (5)
H10	0.760162	0.419717	0.060168	0.030*
C11	0.75190 (10)	0.4170 (3)	0.15534 (13)	0.0201 (5)
C12	0.86966 (11)	0.5331 (4)	0.33263 (14)	0.0276 (6)
H12A	0.853197	0.630672	0.345544	0.041*
H12B	0.909018	0.555278	0.341674	0.041*
H12C	0.867327	0.438085	0.361234	0.041*
C13	0.86310 (14)	0.5252 (4)	0.08306 (18)	0.0388 (8)
H13A	0.852079	0.635565	0.062308	0.058*
H13B	0.851141	0.441861	0.045138	0.058*
H13C	0.903922	0.520693	0.108307	0.058*
C14	0.69173 (11)	0.3609 (4)	0.12740 (15)	0.0281 (6)
H14A	0.689114	0.256234	0.150231	0.042*
H14B	0.678029	0.344715	0.075834	0.042*
H14C	0.668887	0.445202	0.137969	0.042*
C15	0.66014 (10)	0.6322 (3)	0.34395 (12)	0.0158 (4)
C16	0.60623 (10)	0.6846 (3)	0.29970 (12)	0.0165 (4)
C17	0.58109 (10)	0.8079 (3)	0.32509 (13)	0.0180 (5)
H17	0.544597	0.845154	0.295628	0.022*
C18	0.60779 (10)	0.8777 (3)	0.39218 (13)	0.0181 (5)
C19	0.66074 (10)	0.8197 (3)	0.43506 (13)	0.0182 (5)
H19	0.678937	0.864592	0.481461	0.022*
C20	0.68807 (10)	0.6979 (3)	0.41228 (12)	0.0170 (5)
C21	0.57537 (10)	0.6112 (3)	0.22672 (13)	0.0226 (5)
H21A	0.602250	0.583012	0.205552	0.034*
H21B	0.548323	0.692057	0.196465	0.034*
H21C	0.555520	0.510925	0.230779	0.034*
C22	0.58091 (11)	1.0147 (3)	0.41810 (15)	0.0248 (5)
H22A	0.588977	0.998189	0.468685	0.037*
H22B	0.540274	1.012992	0.390963	0.037*
H22C	0.596007	1.121794	0.411482	0.037*
C23	0.74582 (11)	0.6403 (4)	0.46052 (14)	0.0259 (5)
H23A	0.772019	0.659987	0.437416	0.039*
H23B	0.744762	0.521612	0.470074	0.039*
H23C	0.758214	0.701816	0.505408	0.039*
I3	1.03484 (2)	0.22252 (5)	0.98353 (2)	0.02758 (8)	0.5
F11	0.90480 (13)	0.3193 (4)	0.92192 (16)	0.0248 (6)	0.5
F12	0.85170 (12)	0.6024 (4)	0.92448 (16)	0.0269 (7)	0.5
F13	0.91056 (14)	0.8691 (4)	0.99574 (17)	0.0314 (7)	0.5
F14	1.02388 (14)	0.8569 (4)	1.05886 (16)	0.0308 (7)	0.5
F15	1.07926 (18)	0.5765 (7)	1.0519 (3)	0.0298 (13)	0.5
C36	0.9939 (2)	0.4409 (10)	0.9866 (4)	0.0174 (11)	0.5
C37	0.9359 (3)	0.4492 (10)	0.9542 (6)	0.0181 (12)	0.5
C38	0.9076 (2)	0.5946 (6)	0.9559 (2)	0.0194 (8)	0.5
C39	0.9368 (2)	0.7321 (6)	0.9915 (3)	0.0178 (8)	0.5
C40	0.9957 (2)	0.7224 (7)	1.0244 (3)	0.0221 (9)	0.5
C41	1.0237 (3)	0.5789 (9)	1.0216 (4)	0.0179 (11)	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02282 (8)	0.01793 (8)	0.01910 (7)	0.00109 (6)	0.00784 (6)	0.00167 (6)
F1	0.0322 (9)	0.0280 (9)	0.0309 (8)	−0.0065 (7)	0.0160 (7)	0.0071 (7)
F2	0.0236 (8)	0.0378 (10)	0.0403 (9)	−0.0127 (7)	0.0111 (7)	−0.0022 (8)
F3	0.0235 (8)	0.0370 (9)	0.0220 (7)	0.0007 (7)	0.0026 (6)	−0.0008 (7)
F4	0.0278 (8)	0.0221 (8)	0.0210 (7)	0.0031 (6)	0.0115 (6)	0.0056 (6)
F5	0.0231 (7)	0.0187 (7)	0.0257 (7)	−0.0042 (6)	0.0093 (6)	0.0026 (6)
C24	0.0194 (12)	0.0174 (12)	0.0186 (11)	0.0021 (9)	0.0078 (9)	−0.0004 (9)
C25	0.0268 (13)	0.0171 (12)	0.0253 (12)	0.0000 (10)	0.0165 (11)	0.0022 (10)
C26	0.0171 (12)	0.0227 (13)	0.0282 (13)	−0.0025 (9)	0.0102 (10)	−0.0033 (10)
C27	0.0204 (12)	0.0229 (13)	0.0197 (12)	0.0045 (10)	0.0066 (10)	−0.0018 (9)
C28	0.0229 (12)	0.0162 (11)	0.0194 (11)	0.0040 (9)	0.0119 (10)	0.0019 (9)
C29	0.0180 (11)	0.0141 (11)	0.0229 (12)	0.0012 (9)	0.0103 (9)	−0.0023 (9)
I2	0.02439 (8)	0.01677 (8)	0.03445 (9)	0.00219 (6)	0.01867 (7)	0.00160 (6)
F6	0.0360 (10)	0.0621 (13)	0.0212 (8)	0.0210 (9)	0.0063 (7)	0.0077 (8)
F7	0.0635 (13)	0.0625 (14)	0.0377 (10)	0.0140 (11)	0.0352 (10)	−0.0049 (9)
F8	0.0348 (10)	0.0378 (11)	0.0790 (15)	0.0144 (8)	0.0350 (10)	0.0011 (10)
F9	0.0325 (10)	0.0459 (12)	0.0521 (12)	0.0187 (9)	−0.0014 (9)	0.0121 (9)
F10	0.0510 (11)	0.0363 (10)	0.0208 (8)	0.0080 (8)	0.0104 (8)	0.0050 (7)
C30	0.0189 (11)	0.0137 (11)	0.0242 (12)	−0.0009 (9)	0.0105 (10)	−0.0019 (9)
C31	0.0209 (12)	0.0255 (13)	0.0215 (12)	0.0048 (10)	0.0067 (10)	−0.0001 (10)
C32	0.0309 (14)	0.0296 (15)	0.0305 (14)	0.0020 (11)	0.0199 (12)	−0.0033 (11)
C33	0.0203 (13)	0.0222 (13)	0.0477 (17)	0.0032 (10)	0.0171 (12)	−0.0037 (12)
C34	0.0218 (13)	0.0208 (13)	0.0362 (15)	0.0054 (10)	0.0026 (11)	0.0030 (11)
C35	0.0258 (13)	0.0199 (13)	0.0211 (12)	−0.0012 (10)	0.0075 (10)	−0.0010 (10)
Se1	0.01626 (11)	0.01365 (11)	0.02070 (11)	0.00020 (8)	0.00916 (9)	0.00179 (9)
N1	0.0168 (10)	0.0127 (9)	0.0229 (10)	0.0008 (7)	0.0103 (8)	0.0012 (8)
N2	0.0192 (10)	0.0149 (10)	0.0217 (10)	0.0021 (8)	0.0117 (8)	0.0030 (8)
C1	0.0165 (11)	0.0151 (11)	0.0152 (10)	0.0005 (8)	0.0068 (9)	0.0009 (8)
C2	0.0307 (14)	0.0210 (13)	0.0401 (16)	0.0104 (11)	0.0211 (13)	0.0098 (11)
C3	0.0416 (17)	0.0268 (15)	0.0412 (17)	0.0133 (12)	0.0252 (14)	0.0153 (12)
C4	0.0454 (18)	0.0205 (14)	0.0543 (19)	0.0064 (12)	0.0355 (16)	0.0141 (13)
C5	0.0263 (13)	0.0154 (12)	0.0413 (15)	−0.0038 (10)	0.0220 (12)	−0.0016 (11)
C6	0.0197 (11)	0.0133 (11)	0.0213 (11)	0.0034 (9)	0.0119 (10)	0.0031 (9)
C7	0.0187 (12)	0.0153 (11)	0.0264 (12)	0.0053 (9)	0.0099 (10)	0.0033 (9)
C8	0.0193 (12)	0.0204 (13)	0.0375 (15)	0.0050 (10)	0.0157 (11)	0.0061 (11)
C9	0.0330 (14)	0.0182 (12)	0.0330 (14)	0.0110 (10)	0.0234 (12)	0.0101 (10)
C10	0.0352 (15)	0.0213 (13)	0.0215 (12)	0.0076 (11)	0.0144 (11)	0.0022 (10)
C11	0.0224 (12)	0.0159 (12)	0.0220 (12)	0.0024 (9)	0.0087 (10)	−0.0010 (9)
C12	0.0196 (13)	0.0306 (15)	0.0279 (13)	0.0029 (11)	0.0042 (11)	0.0020 (11)
C13	0.0462 (18)	0.0406 (18)	0.0455 (18)	0.0168 (14)	0.0351 (16)	0.0203 (14)
C14	0.0261 (14)	0.0266 (14)	0.0273 (13)	−0.0046 (11)	0.0058 (11)	−0.0046 (11)
C15	0.0165 (11)	0.0133 (11)	0.0200 (11)	0.0009 (8)	0.0096 (9)	0.0031 (9)
C16	0.0162 (11)	0.0175 (11)	0.0161 (11)	−0.0020 (9)	0.0068 (9)	0.0038 (9)
C17	0.0163 (11)	0.0169 (11)	0.0214 (11)	0.0020 (9)	0.0081 (9)	0.0071 (9)
C18	0.0217 (12)	0.0118 (11)	0.0245 (12)	0.0007 (9)	0.0131 (10)	0.0026 (9)
C19	0.0197 (11)	0.0165 (11)	0.0184 (11)	−0.0024 (9)	0.0075 (9)	0.0000 (9)
C20	0.0160 (11)	0.0159 (11)	0.0188 (11)	0.0000 (9)	0.0066 (9)	0.0045 (9)
C21	0.0193 (12)	0.0293 (14)	0.0178 (11)	−0.0017 (10)	0.0058 (10)	0.0003 (10)
C22	0.0275 (13)	0.0163 (12)	0.0343 (14)	0.0031 (10)	0.0160 (11)	−0.0009 (10)
C23	0.0209 (13)	0.0295 (14)	0.0227 (12)	0.0035 (11)	0.0035 (10)	−0.0002 (11)
I3	0.0344 (2)	0.02766 (19)	0.02438 (18)	0.00685 (18)	0.01550 (17)	0.00631 (15)
F11	0.0303 (17)	0.0236 (17)	0.0212 (15)	−0.0121 (14)	0.0108 (13)	−0.0055 (13)
F12	0.0202 (15)	0.0328 (17)	0.0253 (15)	−0.0036 (13)	0.0064 (12)	−0.0010 (13)
F13	0.0387 (19)	0.0269 (17)	0.0301 (17)	0.0028 (14)	0.0151 (15)	−0.0006 (13)
F14	0.0380 (18)	0.0263 (17)	0.0231 (15)	−0.0141 (14)	0.0067 (14)	−0.0046 (13)
F15	0.018 (2)	0.046 (3)	0.023 (2)	−0.004 (2)	0.006 (2)	0.005 (2)
C36	0.017 (3)	0.024 (2)	0.013 (2)	−0.002 (2)	0.008 (2)	0.0026 (16)
C37	0.018 (3)	0.024 (2)	0.015 (2)	−0.005 (2)	0.009 (2)	0.0021 (17)
C38	0.0190 (18)	0.0247 (19)	0.0147 (16)	−0.0065 (16)	0.0068 (15)	0.0010 (15)
C39	0.0155 (19)	0.0230 (19)	0.0114 (16)	−0.0114 (16)	0.0013 (15)	−0.0010 (15)
C40	0.019 (2)	0.028 (2)	0.0150 (17)	−0.0067 (18)	0.0023 (16)	−0.0003 (16)
C41	0.015 (3)	0.025 (2)	0.0139 (19)	−0.007 (2)	0.006 (2)	0.0023 (16)

Geometric parameters (Å, º)

I1—C24	2.109 (2)	C8—C9	1.384 (4)
F1—C25	1.344 (3)	C9—C10	1.394 (4)
F2—C26	1.340 (3)	C9—C13	1.511 (4)
F3—C27	1.339 (3)	C10—H10	0.9500
F4—C28	1.347 (3)	C10—C11	1.399 (3)
F5—C29	1.345 (3)	C11—C14	1.506 (4)
C24—C25	1.384 (3)	C12—H12A	0.9800
C24—C29	1.387 (3)	C12—H12B	0.9800
C25—C26	1.383 (4)	C12—H12C	0.9800
C26—C27	1.382 (4)	C13—H13A	0.9800
C27—C28	1.383 (4)	C13—H13B	0.9800
C28—C29	1.377 (3)	C13—H13C	0.9800
I2—C30	2.096 (2)	C14—H14A	0.9800
F6—C31	1.341 (3)	C14—H14B	0.9800
F7—C32	1.342 (3)	C14—H14C	0.9800
F8—C33	1.343 (3)	C15—C16	1.401 (3)
F9—C34	1.346 (3)	C15—C20	1.401 (3)
F10—C35	1.340 (3)	C16—C17	1.396 (3)
C30—C31	1.377 (3)	C16—C21	1.510 (3)
C30—C35	1.379 (3)	C17—H17	0.9500
C31—C32	1.380 (4)	C17—C18	1.390 (3)
C32—C33	1.373 (4)	C18—C19	1.389 (3)
C33—C34	1.368 (4)	C18—C22	1.509 (3)
C34—C35	1.381 (4)	C19—H19	0.9500
Se1—C1	1.876 (2)	C19—C20	1.394 (3)
N1—C1	1.353 (3)	C20—C23	1.508 (3)
N1—C5	1.485 (3)	C21—H21A	0.9800
N1—C15	1.447 (3)	C21—H21B	0.9800
N2—C1	1.348 (3)	C21—H21C	0.9800
N2—C2	1.501 (3)	C22—H22A	0.9800
N2—C6	1.451 (3)	C22—H22B	0.9800
C2—H2A	0.9900	C22—H22C	0.9800
C2—H2B	0.9900	C23—H23A	0.9800
C2—C3	1.513 (4)	C23—H23B	0.9800
C3—H3A	0.9900	C23—H23C	0.9800
C3—H3B	0.9900	I3—C36	2.071 (8)
C3—C4	1.526 (4)	F11—C37	1.331 (8)
C4—H4A	0.9900	F12—C38	1.337 (5)
C4—H4B	0.9900	F13—C39	1.319 (6)
C4—C5	1.520 (4)	F14—C40	1.343 (6)
C5—H5A	0.9900	F15—C41	1.327 (6)
C5—H5B	0.9900	C36—C37	1.386 (6)
C6—C7	1.391 (3)	C36—C41	1.384 (6)
C6—C11	1.400 (3)	C37—C38	1.392 (7)
C7—C8	1.398 (3)	C38—C39	1.380 (5)
C7—C12	1.506 (4)	C39—C40	1.411 (5)
C8—H8	0.9500	C40—C41	1.379 (7)
C25—C24—I1	120.00 (18)	C10—C9—C13	120.3 (3)
C25—C24—C29	117.3 (2)	C9—C10—H10	119.1
C29—C24—I1	122.61 (18)	C9—C10—C11	121.8 (2)
F1—C25—C24	120.4 (2)	C11—C10—H10	119.1
F1—C25—C26	117.6 (2)	C6—C11—C14	121.3 (2)
C26—C25—C24	122.0 (2)	C10—C11—C6	117.7 (2)
F2—C26—C25	120.7 (2)	C10—C11—C14	121.0 (2)
F2—C26—C27	119.8 (2)	C7—C12—H12A	109.5
C27—C26—C25	119.4 (2)	C7—C12—H12B	109.5
F3—C27—C26	120.2 (2)	C7—C12—H12C	109.5
F3—C27—C28	120.3 (2)	H12A—C12—H12B	109.5
C26—C27—C28	119.5 (2)	H12A—C12—H12C	109.5
F4—C28—C27	119.1 (2)	H12B—C12—H12C	109.5
F4—C28—C29	120.8 (2)	C9—C13—H13A	109.5
C29—C28—C27	120.1 (2)	C9—C13—H13B	109.5
F5—C29—C24	120.4 (2)	C9—C13—H13C	109.5
F5—C29—C28	118.0 (2)	H13A—C13—H13B	109.5
C28—C29—C24	121.6 (2)	H13A—C13—H13C	109.5
C31—C30—I2	122.14 (18)	H13B—C13—H13C	109.5
C31—C30—C35	116.9 (2)	C11—C14—H14A	109.5
C35—C30—I2	120.96 (18)	C11—C14—H14B	109.5
F6—C31—C30	120.6 (2)	C11—C14—H14C	109.5
F6—C31—C32	117.5 (2)	H14A—C14—H14B	109.5
C30—C31—C32	121.9 (2)	H14A—C14—H14C	109.5
F7—C32—C31	120.5 (3)	H14B—C14—H14C	109.5
F7—C32—C33	119.6 (2)	C16—C15—N1	118.9 (2)
C33—C32—C31	119.9 (3)	C16—C15—C20	121.7 (2)
F8—C33—C32	119.8 (3)	C20—C15—N1	119.4 (2)
F8—C33—C34	120.7 (3)	C15—C16—C21	121.9 (2)
C34—C33—C32	119.4 (2)	C17—C16—C15	118.0 (2)
F9—C34—C33	119.6 (3)	C17—C16—C21	120.2 (2)
F9—C34—C35	120.5 (3)	C16—C17—H17	119.0
C33—C34—C35	119.9 (2)	C18—C17—C16	122.0 (2)
F10—C35—C30	120.1 (2)	C18—C17—H17	119.0
F10—C35—C34	117.9 (2)	C17—C18—C22	121.5 (2)
C30—C35—C34	122.0 (2)	C19—C18—C17	118.2 (2)
C1—N1—C5	121.5 (2)	C19—C18—C22	120.2 (2)
C1—N1—C15	120.85 (19)	C18—C19—H19	118.9
C15—N1—C5	116.73 (19)	C18—C19—C20	122.2 (2)
C1—N2—C2	127.6 (2)	C20—C19—H19	118.9
C1—N2—C6	120.22 (19)	C15—C20—C23	121.9 (2)
C6—N2—C2	112.09 (19)	C19—C20—C15	117.9 (2)
N1—C1—Se1	118.93 (17)	C19—C20—C23	120.2 (2)
N2—C1—Se1	121.44 (17)	C16—C21—H21A	109.5
N2—C1—N1	119.6 (2)	C16—C21—H21B	109.5
N2—C2—H2A	108.4	C16—C21—H21C	109.5
N2—C2—H2B	108.4	H21A—C21—H21B	109.5
N2—C2—C3	115.4 (2)	H21A—C21—H21C	109.5
H2A—C2—H2B	107.5	H21B—C21—H21C	109.5
C3—C2—H2A	108.4	C18—C22—H22A	109.5
C3—C2—H2B	108.4	C18—C22—H22B	109.5
C2—C3—H3A	109.2	C18—C22—H22C	109.5
C2—C3—H3B	109.2	H22A—C22—H22B	109.5
C2—C3—C4	112.2 (3)	H22A—C22—H22C	109.5
H3A—C3—H3B	107.9	H22B—C22—H22C	109.5
C4—C3—H3A	109.2	C20—C23—H23A	109.5
C4—C3—H3B	109.2	C20—C23—H23B	109.5
C3—C4—H4A	109.5	C20—C23—H23C	109.5
C3—C4—H4B	109.5	H23A—C23—H23B	109.5
H4A—C4—H4B	108.1	H23A—C23—H23C	109.5
C5—C4—C3	110.5 (2)	H23B—C23—H23C	109.5
C5—C4—H4A	109.5	C37—C36—I3	120.0 (5)
C5—C4—H4B	109.5	C41—C36—I3	120.7 (4)
N1—C5—C4	112.7 (2)	C41—C36—C37	119.3 (6)
N1—C5—H5A	109.1	F11—C37—C36	122.2 (6)
N1—C5—H5B	109.1	F11—C37—C38	116.9 (5)
C4—C5—H5A	109.1	C36—C37—C38	120.9 (7)
C4—C5—H5B	109.1	F12—C38—C37	120.8 (5)
H5A—C5—H5B	107.8	F12—C38—C39	118.9 (4)
C7—C6—N2	119.3 (2)	C39—C38—C37	120.3 (5)
C7—C6—C11	122.1 (2)	F13—C39—C38	121.2 (4)
C11—C6—N2	118.4 (2)	F13—C39—C40	120.4 (4)
C6—C7—C8	117.8 (2)	C38—C39—C40	118.4 (5)
C6—C7—C12	121.9 (2)	F14—C40—C39	118.0 (5)
C8—C7—C12	120.2 (2)	F14—C40—C41	120.9 (5)
C7—C8—H8	118.9	C41—C40—C39	121.1 (5)
C9—C8—C7	122.2 (2)	F15—C41—C36	120.9 (5)
C9—C8—H8	118.9	F15—C41—C40	119.0 (5)
C8—C9—C10	118.3 (2)	C40—C41—C36	120.0 (5)
C8—C9—C13	121.3 (3)
I1—C24—C25—F1	−3.1 (3)	C2—N2—C1—N1	−19.9 (4)
I1—C24—C25—C26	175.48 (19)	C2—N2—C6—C7	−81.0 (3)
I1—C24—C29—F5	2.8 (3)	C2—N2—C6—C11	94.0 (3)
I1—C24—C29—C28	−176.29 (18)	C2—C3—C4—C5	−37.7 (3)
F1—C25—C26—F2	−0.2 (4)	C3—C4—C5—N1	−48.0 (3)
F1—C25—C26—C27	179.7 (2)	C5—N1—C1—Se1	159.24 (18)
F2—C26—C27—F3	1.6 (4)	C5—N1—C1—N2	−21.6 (3)
F2—C26—C27—C28	−179.7 (2)	C5—N1—C15—C16	−71.7 (3)
F3—C27—C28—F4	−1.1 (3)	C5—N1—C15—C20	106.6 (3)
F3—C27—C28—C29	177.3 (2)	C6—N2—C1—Se1	−18.0 (3)
F4—C28—C29—F5	0.0 (3)	C6—N2—C1—N1	162.8 (2)
F4—C28—C29—C24	179.0 (2)	C6—N2—C2—C3	154.0 (2)
C24—C25—C26—F2	−178.7 (2)	C6—C7—C8—C9	0.0 (4)
C24—C25—C26—C27	1.1 (4)	C7—C6—C11—C10	−2.9 (4)
C25—C24—C29—F5	179.9 (2)	C7—C6—C11—C14	177.4 (2)
C25—C24—C29—C28	0.8 (4)	C7—C8—C9—C10	−2.0 (4)
C25—C26—C27—F3	−178.2 (2)	C7—C8—C9—C13	175.2 (2)
C25—C26—C27—C28	0.4 (4)	C8—C9—C10—C11	1.6 (4)
C26—C27—C28—F4	−179.7 (2)	C9—C10—C11—C6	0.8 (4)
C26—C27—C28—C29	−1.3 (4)	C9—C10—C11—C14	−179.5 (2)
C27—C28—C29—F5	−178.4 (2)	C11—C6—C7—C8	2.5 (4)
C27—C28—C29—C24	0.7 (4)	C11—C6—C7—C12	178.6 (2)
C29—C24—C25—F1	179.8 (2)	C12—C7—C8—C9	−176.2 (2)
C29—C24—C25—C26	−1.7 (4)	C13—C9—C10—C11	−175.6 (2)
I2—C30—C31—F6	−3.2 (4)	C15—N1—C1—Se1	−9.2 (3)
I2—C30—C31—C32	177.0 (2)	C15—N1—C1—N2	170.0 (2)
I2—C30—C35—F10	3.7 (3)	C15—N1—C5—C4	−105.4 (2)
I2—C30—C35—C34	−177.0 (2)	C15—C16—C17—C18	−0.3 (3)
F6—C31—C32—F7	−0.9 (4)	C16—C15—C20—C19	−0.7 (3)
F6—C31—C32—C33	−179.5 (3)	C16—C15—C20—C23	179.2 (2)
F7—C32—C33—F8	0.1 (4)	C16—C17—C18—C19	−1.1 (3)
F7—C32—C33—C34	−178.8 (3)	C16—C17—C18—C22	178.0 (2)
F8—C33—C34—F9	0.3 (4)	C17—C18—C19—C20	1.6 (4)
F8—C33—C34—C35	−178.7 (3)	C18—C19—C20—C15	−0.7 (3)
F9—C34—C35—F10	0.0 (4)	C18—C19—C20—C23	179.3 (2)
F9—C34—C35—C30	−179.3 (2)	C20—C15—C16—C17	1.2 (3)
C30—C31—C32—F7	178.9 (3)	C20—C15—C16—C21	−178.5 (2)
C30—C31—C32—C33	0.2 (4)	C21—C16—C17—C18	179.4 (2)
C31—C30—C35—F10	−178.8 (2)	C22—C18—C19—C20	−177.5 (2)
C31—C30—C35—C34	0.5 (4)	I3—C36—C37—F11	1.6 (12)
C31—C32—C33—F8	178.8 (3)	I3—C36—C37—C38	179.8 (6)
C31—C32—C33—C34	−0.1 (4)	I3—C36—C41—F15	2.2 (6)
C32—C33—C34—F9	179.1 (3)	I3—C36—C41—C40	−178.7 (7)
C32—C33—C34—C35	0.1 (4)	F11—C37—C38—F12	−1.8 (11)
C33—C34—C35—F10	179.0 (2)	F11—C37—C38—C39	176.7 (6)
C33—C34—C35—C30	−0.4 (4)	F12—C38—C39—F13	0.9 (7)
C35—C30—C31—F6	179.3 (2)	F12—C38—C39—C40	−179.9 (4)
C35—C30—C31—C32	−0.4 (4)	F13—C39—C40—F14	−1.0 (7)
N1—C15—C16—C17	179.4 (2)	F13—C39—C40—C41	178.7 (5)
N1—C15—C16—C21	−0.2 (3)	F14—C40—C41—F15	−1.8 (10)
N1—C15—C20—C19	−178.9 (2)	F14—C40—C41—C36	179.1 (4)
N1—C15—C20—C23	1.0 (3)	C36—C37—C38—F12	179.9 (7)
N2—C2—C3—C4	78.5 (3)	C36—C37—C38—C39	−1.5 (11)
N2—C6—C7—C8	177.3 (2)	C37—C36—C41—F15	−178.6 (10)
N2—C6—C7—C12	−6.6 (3)	C37—C36—C41—C40	0.5 (8)
N2—C6—C11—C10	−177.7 (2)	C37—C38—C39—F13	−177.7 (6)
N2—C6—C11—C14	2.6 (3)	C37—C38—C39—C40	1.5 (8)
C1—N1—C5—C4	85.7 (3)	C38—C39—C40—F14	179.9 (4)
C1—N1—C15—C16	97.3 (3)	C38—C39—C40—C41	−0.4 (8)
C1—N1—C15—C20	−84.4 (3)	C39—C40—C41—F15	178.5 (6)
C1—N2—C2—C3	−23.5 (4)	C39—C40—C41—C36	−0.6 (8)
C1—N2—C6—C7	96.7 (3)	C41—C36—C37—F11	−177.7 (6)
C1—N2—C6—C11	−88.3 (3)	C41—C36—C37—C38	0.5 (11)
C2—N2—C1—Se1	159.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···I2^i	0.99	3.25	3.852 (3)	121
C3—H3B···F12^i	0.99	2.54	3.456 (4)	155
C5—H5B···F4^ii	0.99	2.55	3.530 (3)	170

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, y+1/2, −z+1/2.

(2SDiazMesS_TIE)

Crystal data

CI2·C23H30N2S	Z = 2
Mr = 632.36	F(000) = 620
Triclinic, P1	Dx = 1.726 Mg m^−3
a = 7.9170 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.6457 (8) Å	Cell parameters from 9937 reflections
c = 15.0306 (10) Å	θ = 2.7–29.6°
α = 67.358 (2)°	µ = 2.68 mm^−1
β = 83.953 (2)°	T = 100 K
γ = 72.067 (2)°	Plate, yellow
V = 1216.73 (15) Å^3	0.23 × 0.13 × 0.05 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	6164 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.038
φ and ω scans	θmax = 29.6°, θmin = 2.9°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −11→11
Tmin = 0.598, Tmax = 0.746	k = −16→16
38610 measured reflections	l = −20→20
6789 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.070	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + 5.6607P] where P = (Fo^2 + 2Fc^2)/3
6789 reflections	(Δ/σ)max = 0.001
384 parameters	Δρmax = 3.79 e Å^−3
30 restraints	Δρmin = −3.62 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
I2	0.02074 (3)	0.69512 (2)	0.35421 (2)	0.01993 (5)
I1	−0.04797 (3)	0.39623 (2)	0.38596 (2)	0.02203 (6)
C24A	−0.0054 (5)	0.5161 (4)	0.4525 (3)	0.0140 (13)	0.771 (16)
C24B	0.0104 (15)	0.5549 (14)	0.4925 (10)	0.016 (5)	0.229 (16)
S1	−0.05164 (10)	0.25499 (10)	0.24142 (6)	0.02858 (19)
N1	−0.2040 (3)	0.1818 (3)	0.13206 (18)	0.0171 (5)
N2A	−0.3759 (8)	0.2160 (6)	0.2576 (4)	0.0151 (10)	0.503 (5)
N2B	−0.3158 (8)	0.1577 (6)	0.2892 (4)	0.0142 (10)	0.497 (5)
C1	−0.2109 (4)	0.2052 (3)	0.2148 (2)	0.0161 (5)
C2A	−0.3044 (11)	0.1109 (9)	0.1017 (6)	0.0213 (15)	0.503 (5)
H2AA	−0.222447	0.058521	0.067651	0.026*	0.503 (5)
H2AB	−0.400371	0.175629	0.055700	0.026*	0.503 (5)
C2B	−0.3554 (13)	0.1642 (10)	0.0943 (7)	0.0276 (18)	0.497 (5)
H2BA	−0.329677	0.070592	0.106472	0.033*	0.497 (5)
H2BB	−0.361914	0.211373	0.023583	0.033*	0.497 (5)
C3A	−0.3847 (9)	0.0222 (6)	0.1856 (5)	0.0228 (13)	0.503 (5)
H3AA	−0.295079	−0.027349	0.238440	0.027*	0.503 (5)
H3AB	−0.412140	−0.041273	0.164930	0.027*	0.503 (5)
C3B	−0.5360 (9)	0.2084 (7)	0.1346 (5)	0.0266 (15)	0.497 (5)
H3BA	−0.550783	0.293734	0.138697	0.032*	0.497 (5)
H3BB	−0.628550	0.220207	0.089723	0.032*	0.497 (5)
C4A	−0.554 (3)	0.0925 (19)	0.2250 (15)	0.016 (3)	0.503 (5)
H4AA	−0.566360	0.041121	0.294040	0.019*	0.503 (5)
H4AB	−0.659056	0.102455	0.189433	0.019*	0.503 (5)
C4B	−0.562 (3)	0.116 (2)	0.2306 (17)	0.025 (4)	0.497 (5)
H4BA	−0.598930	0.045698	0.223576	0.030*	0.497 (5)
H4BB	−0.658345	0.161154	0.263668	0.030*	0.497 (5)
C5A	−0.5418 (7)	0.2278 (6)	0.2130 (4)	0.0186 (12)	0.503 (5)
H5AA	−0.545078	0.282553	0.143545	0.022*	0.503 (5)
H5AB	−0.645380	0.270861	0.243585	0.022*	0.503 (5)
C5B	−0.3917 (8)	0.0562 (6)	0.2918 (4)	0.0166 (11)	0.497 (5)
H5BA	−0.417984	0.007176	0.359217	0.020*	0.497 (5)
H5BB	−0.304133	−0.005552	0.267014	0.020*	0.497 (5)
C6	−0.0611 (4)	0.2039 (3)	0.0662 (2)	0.0167 (5)
C7	−0.0802 (5)	0.3283 (4)	−0.0047 (2)	0.0284 (6)
C8	0.0551 (5)	0.3462 (4)	−0.0705 (3)	0.0355 (6)
H8	0.043715	0.429829	−0.119058	0.043*
C9	0.2062 (5)	0.2453 (5)	−0.0673 (3)	0.0392 (6)
C10	0.2211 (5)	0.1240 (4)	0.0034 (2)	0.0337 (5)
H10	0.324821	0.054568	0.006105	0.040*
C11	0.0893 (4)	0.1003 (4)	0.0707 (2)	0.0266 (5)
C12	−0.2404 (5)	0.4402 (3)	−0.0083 (3)	0.0342 (8)
H12A	−0.345612	0.425164	−0.025410	0.051*
H12B	−0.223361	0.520746	−0.056903	0.051*
H12C	−0.256777	0.447867	0.054908	0.051*
C13	0.3537 (6)	0.2703 (7)	−0.1383 (3)	0.0683 (12)
H13A	0.302970	0.340020	−0.199025	0.103*
H13B	0.416391	0.190799	−0.150139	0.103*
H13C	0.437084	0.296147	−0.111520	0.103*
C14	0.1087 (5)	−0.0326 (3)	0.1473 (3)	0.0341 (8)
H14A	0.083610	−0.025065	0.210450	0.051*
H14B	0.230270	−0.088118	0.147500	0.051*
H14C	0.024999	−0.071042	0.134010	0.051*
C15A	−0.3950 (7)	0.2294 (6)	0.3494 (3)	0.0138 (14)	0.503 (5)
C16A	−0.4848 (9)	0.3503 (5)	0.3536 (4)	0.0110 (14)	0.503 (5)
C17A	−0.5172 (11)	0.3638 (5)	0.4422 (6)	0.0164 (19)	0.503 (5)
H17A	−0.578501	0.446441	0.445079	0.020*	0.503 (5)
C18A	−0.4598 (10)	0.2565 (6)	0.5268 (4)	0.017 (2)	0.503 (5)
C19A	−0.3701 (7)	0.1357 (5)	0.5226 (3)	0.0166 (12)	0.503 (5)
H19A	−0.330884	0.062305	0.580419	0.020*	0.503 (5)
C20A	−0.3377 (7)	0.1221 (4)	0.4340 (4)	0.0158 (12)	0.503 (5)
C15B	−0.3471 (8)	0.1947 (5)	0.3725 (3)	0.0122 (14)	0.497 (5)
C16B	−0.4752 (9)	0.3093 (5)	0.3687 (5)	0.0175 (17)	0.497 (5)
C17B	−0.5191 (10)	0.3365 (6)	0.4519 (6)	0.0134 (17)	0.497 (5)
H17B	−0.606741	0.414828	0.449293	0.016*	0.497 (5)
C18B	−0.4349 (9)	0.2493 (7)	0.5390 (5)	0.019 (2)	0.497 (5)
C19B	−0.3067 (8)	0.1347 (5)	0.5428 (3)	0.0172 (13)	0.497 (5)
H19B	−0.249154	0.075062	0.602283	0.021*	0.497 (5)
C20B	−0.2628 (7)	0.1074 (4)	0.4596 (3)	0.0152 (11)	0.497 (5)
C21A	−0.5423 (9)	0.4706 (8)	0.2622 (5)	0.0217 (13)	0.503 (5)
H21A	−0.455371	0.463892	0.211574	0.033*	0.503 (5)
H21B	−0.549791	0.548204	0.275286	0.033*	0.503 (5)
H21C	−0.658872	0.477309	0.240727	0.033*	0.503 (5)
C21B	−0.5621 (9)	0.4107 (8)	0.2734 (5)	0.0216 (13)	0.497 (5)
H21D	−0.471769	0.420607	0.223382	0.032*	0.497 (5)
H21E	−0.617531	0.494191	0.280786	0.032*	0.497 (5)
H21F	−0.652794	0.382519	0.254741	0.032*	0.497 (5)
C22A	−0.496 (3)	0.277 (3)	0.625 (2)	0.026 (7)	0.503 (5)
H22A	−0.491497	0.363745	0.615888	0.040*	0.503 (5)
H22B	−0.405946	0.211066	0.672758	0.040*	0.503 (5)
H22C	−0.614057	0.268356	0.647800	0.040*	0.503 (5)
C22B	−0.497 (3)	0.269 (3)	0.630 (2)	0.026 (7)	0.497 (5)
H22D	−0.570851	0.358637	0.615343	0.039*	0.497 (5)
H22E	−0.393757	0.251592	0.669211	0.039*	0.497 (5)
H22F	−0.566007	0.208981	0.665674	0.039*	0.497 (5)
C23A	−0.2436 (8)	−0.0127 (6)	0.4314 (5)	0.0221 (13)	0.503 (5)
H23A	−0.329192	−0.045569	0.413137	0.033*	0.503 (5)
H23B	−0.193018	−0.072185	0.495235	0.033*	0.503 (5)
H23C	−0.148411	−0.006597	0.384022	0.033*	0.503 (5)
C23B	−0.1226 (9)	−0.0203 (6)	0.4656 (5)	0.0222 (13)	0.497 (5)
H23D	−0.181288	−0.081295	0.462038	0.033*	0.497 (5)
H23E	−0.056531	−0.058285	0.526794	0.033*	0.497 (5)
H23F	−0.040463	−0.003054	0.411899	0.033*	0.497 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I2	0.02243 (10)	0.01378 (9)	0.02133 (10)	−0.00640 (7)	0.00258 (7)	−0.00385 (7)
I1	0.01672 (9)	0.02687 (10)	0.03117 (11)	−0.00564 (7)	0.00086 (7)	−0.02065 (9)
C24A	0.0135 (16)	0.0101 (18)	0.020 (3)	−0.0042 (12)	0.0019 (13)	−0.0069 (18)
C24B	0.009 (5)	0.024 (9)	0.013 (7)	−0.003 (4)	0.001 (4)	−0.007 (6)
S1	0.0169 (3)	0.0575 (6)	0.0277 (4)	−0.0152 (4)	0.0073 (3)	−0.0315 (4)
N1	0.0161 (11)	0.0232 (12)	0.0151 (11)	−0.0081 (9)	0.0010 (9)	−0.0089 (9)
N2A	0.014 (2)	0.017 (3)	0.017 (3)	−0.004 (2)	0.001 (2)	−0.010 (2)
N2B	0.014 (2)	0.015 (3)	0.016 (3)	−0.004 (2)	0.000 (2)	−0.008 (2)
C1	0.0178 (13)	0.0158 (12)	0.0181 (13)	−0.0063 (10)	0.0052 (10)	−0.0101 (10)
C2A	0.019 (4)	0.033 (4)	0.021 (3)	−0.011 (3)	0.004 (3)	−0.018 (4)
C2B	0.030 (5)	0.035 (5)	0.022 (4)	−0.011 (4)	−0.005 (3)	−0.012 (4)
C3A	0.024 (3)	0.020 (3)	0.029 (3)	−0.007 (2)	0.002 (2)	−0.013 (2)
C3B	0.028 (3)	0.024 (3)	0.025 (3)	−0.007 (3)	−0.012 (3)	−0.002 (3)
C4A	0.017 (5)	0.015 (7)	0.022 (4)	−0.011 (5)	0.002 (3)	−0.009 (4)
C4B	0.018 (5)	0.018 (7)	0.041 (7)	−0.002 (5)	−0.010 (4)	−0.012 (5)
C5A	0.011 (2)	0.025 (3)	0.021 (3)	−0.004 (2)	0.000 (2)	−0.011 (2)
C5B	0.016 (3)	0.017 (3)	0.020 (3)	−0.006 (2)	−0.001 (2)	−0.009 (2)
C6	0.0174 (13)	0.0226 (13)	0.0121 (12)	−0.0052 (11)	0.0014 (10)	−0.0095 (10)
C7	0.0241 (11)	0.0411 (13)	0.0150 (10)	−0.0077 (10)	−0.0010 (9)	−0.0063 (9)
C8	0.0268 (10)	0.0487 (12)	0.0177 (9)	−0.0058 (9)	0.0001 (8)	−0.0023 (9)
C9	0.0277 (9)	0.0550 (11)	0.0183 (8)	−0.0020 (9)	0.0018 (8)	−0.0041 (8)
C10	0.0258 (10)	0.0495 (12)	0.0165 (9)	0.0006 (9)	0.0004 (8)	−0.0114 (9)
C11	0.0235 (11)	0.0418 (13)	0.0150 (10)	−0.0018 (10)	−0.0022 (9)	−0.0164 (9)
C12	0.038 (2)	0.0213 (16)	0.0310 (18)	0.0007 (14)	−0.0063 (15)	−0.0023 (14)
C13	0.0347 (16)	0.103 (2)	0.0261 (15)	−0.0021 (17)	0.0068 (14)	0.0040 (16)
C14	0.041 (2)	0.0215 (16)	0.0358 (19)	0.0031 (14)	−0.0120 (16)	−0.0133 (14)
C15A	0.010 (3)	0.017 (4)	0.015 (3)	−0.005 (3)	0.002 (2)	−0.006 (3)
C16A	0.010 (3)	0.012 (4)	0.012 (3)	−0.007 (2)	0.004 (2)	−0.003 (3)
C17A	0.017 (4)	0.015 (3)	0.020 (4)	−0.010 (3)	0.004 (3)	−0.007 (3)
C18A	0.009 (3)	0.023 (5)	0.027 (5)	−0.006 (3)	0.009 (3)	−0.019 (4)
C19A	0.017 (3)	0.018 (3)	0.014 (3)	−0.007 (2)	0.000 (2)	−0.003 (2)
C20A	0.014 (3)	0.018 (3)	0.019 (3)	−0.003 (2)	−0.001 (2)	−0.010 (3)
C15B	0.012 (3)	0.014 (4)	0.012 (3)	−0.005 (3)	0.001 (3)	−0.006 (3)
C16B	0.020 (3)	0.011 (4)	0.018 (3)	−0.006 (3)	0.000 (3)	−0.001 (3)
C17B	0.011 (3)	0.014 (3)	0.017 (4)	−0.006 (3)	0.008 (3)	−0.007 (3)
C18B	0.026 (5)	0.023 (5)	0.009 (3)	−0.013 (3)	0.004 (3)	−0.003 (3)
C19B	0.016 (3)	0.022 (3)	0.016 (3)	−0.009 (3)	0.005 (2)	−0.008 (2)
C20B	0.015 (3)	0.013 (2)	0.016 (3)	−0.003 (2)	−0.001 (2)	−0.004 (2)
C21A	0.027 (3)	0.016 (3)	0.017 (3)	0.001 (3)	−0.002 (2)	−0.006 (3)
C21B	0.024 (3)	0.015 (3)	0.019 (3)	0.000 (3)	0.003 (2)	−0.005 (3)
C22A	0.017 (9)	0.036 (10)	0.017 (8)	−0.008 (7)	0.004 (6)	−0.001 (6)
C22B	0.034 (13)	0.025 (8)	0.020 (10)	−0.005 (7)	0.012 (7)	−0.016 (7)
C23A	0.024 (3)	0.019 (3)	0.023 (3)	−0.002 (2)	0.000 (2)	−0.010 (2)
C23B	0.024 (3)	0.017 (3)	0.022 (3)	0.001 (2)	−0.005 (2)	−0.008 (2)

Geometric parameters (Å, º)

I2—C24A	2.098 (4)	C12—H12A	0.9800
I2—C24B	2.104 (14)	C12—H12B	0.9800
I1—C24A	2.121 (4)	C12—H12C	0.9800
I1—C24B^i	2.183 (14)	C13—H13A	0.9800
C24A—C24A^i	1.334 (8)	C13—H13B	0.9800
C24B—C24B^i	1.27 (3)	C13—H13C	0.9800
S1—C1	1.680 (3)	C14—H14A	0.9800
N1—C1	1.364 (4)	C14—H14B	0.9800
N1—C2A	1.514 (9)	C14—H14C	0.9800
N1—C2B	1.478 (9)	C15A—C16A	1.3900
N1—C6	1.440 (4)	C15A—C20A	1.3900
N2A—C1	1.386 (6)	C16A—C17A	1.3900
N2A—C5A	1.483 (8)	C16A—C21A	1.522 (8)
N2A—C15A	1.435 (7)	C17A—H17A	0.9500
N2B—C1	1.363 (6)	C17A—C18A	1.3900
N2B—C5B	1.469 (7)	C18A—C19A	1.3900
N2B—C15B	1.449 (7)	C18A—C22A	1.57 (3)
C2A—H2AA	0.9900	C19A—H19A	0.9500
C2A—H2AB	0.9900	C19A—C20A	1.3900
C2A—C3A	1.515 (11)	C20A—C23A	1.530 (7)
C2B—H2BA	0.9900	C15B—C16B	1.3900
C2B—H2BB	0.9900	C15B—C20B	1.3900
C2B—C3B	1.509 (12)	C16B—C17B	1.3900
C3A—H3AA	0.9900	C16B—C21B	1.525 (8)
C3A—H3AB	0.9900	C17B—H17B	0.9500
C3A—C4A	1.53 (2)	C17B—C18B	1.3900
C3B—H3BA	0.9900	C18B—C19B	1.3900
C3B—H3BB	0.9900	C18B—C22B	1.48 (2)
C3B—C4B	1.47 (3)	C19B—H19B	0.9500
C4A—H4AA	0.9900	C19B—C20B	1.3900
C4A—H4AB	0.9900	C20B—C23B	1.535 (7)
C4A—C5A	1.55 (2)	C21A—H21A	0.9800
C4B—H4BA	0.9900	C21A—H21B	0.9800
C4B—H4BB	0.9900	C21A—H21C	0.9800
C4B—C5B	1.53 (3)	C21B—H21D	0.9800
C5A—H5AA	0.9900	C21B—H21E	0.9800
C5A—H5AB	0.9900	C21B—H21F	0.9800
C5B—H5BA	0.9900	C22A—H22A	0.9800
C5B—H5BB	0.9900	C22A—H22B	0.9800
C6—C7	1.402 (5)	C22A—H22C	0.9800
C6—C11	1.396 (4)	C22B—H22D	0.9800
C7—C8	1.387 (5)	C22B—H22E	0.9800
C7—C12	1.501 (5)	C22B—H22F	0.9800
C8—H8	0.9500	C23A—H23A	0.9800
C8—C9	1.385 (6)	C23A—H23B	0.9800
C9—C10	1.381 (6)	C23A—H23C	0.9800
C9—C13	1.514 (6)	C23B—H23D	0.9800
C10—H10	0.9500	C23B—H23E	0.9800
C10—C11	1.389 (5)	C23B—H23F	0.9800
C11—C14	1.504 (5)
C24A—I1—C24B^i	24.7 (4)	C7—C12—H12B	109.5
I2—C24A—I1	113.65 (19)	C7—C12—H12C	109.5
C24A^i—C24A—I2	121.6 (4)	H12A—C12—H12B	109.5
C24A^i—C24A—I1	124.8 (4)	H12A—C12—H12C	109.5
I2—C24B—I1^i	116.3 (7)	H12B—C12—H12C	109.5
C24B^i—C24B—I2	123.6 (14)	C9—C13—H13A	109.5
C1—N1—C2A	130.7 (4)	C9—C13—H13B	109.5
C1—N1—C2B	123.2 (4)	C9—C13—H13C	109.5
C1—N1—C6	119.2 (2)	H13A—C13—H13B	109.5
C6—N1—C2A	109.1 (4)	H13A—C13—H13C	109.5
C6—N1—C2B	116.1 (4)	H13B—C13—H13C	109.5
C1—N2A—C5A	125.7 (5)	C11—C14—H14A	109.5
C1—N2A—C15A	118.3 (4)	C11—C14—H14B	109.5
C15A—N2A—C5A	115.7 (5)	C11—C14—H14C	109.5
C1—N2B—C5B	120.3 (4)	H14A—C14—H14B	109.5
C1—N2B—C15B	123.2 (4)	H14A—C14—H14C	109.5
C15B—N2B—C5B	116.4 (5)	H14B—C14—H14C	109.5
N1—C1—S1	120.6 (2)	C16A—C15A—N2A	118.8 (4)
N1—C1—N2A	113.3 (3)	C16A—C15A—C20A	120.0
N2A—C1—S1	124.2 (3)	C20A—C15A—N2A	121.0 (4)
N2B—C1—S1	116.0 (3)	C15A—C16A—C21A	121.2 (5)
N2B—C1—N1	121.2 (3)	C17A—C16A—C15A	120.0
N1—C2A—H2AA	109.0	C17A—C16A—C21A	118.8 (5)
N1—C2A—H2AB	109.0	C16A—C17A—H17A	120.0
N1—C2A—C3A	113.1 (6)	C16A—C17A—C18A	120.0
H2AA—C2A—H2AB	107.8	C18A—C17A—H17A	120.0
C3A—C2A—H2AA	109.0	C17A—C18A—C19A	120.0
C3A—C2A—H2AB	109.0	C17A—C18A—C22A	118.2 (11)
N1—C2B—H2BA	108.0	C19A—C18A—C22A	121.7 (11)
N1—C2B—H2BB	108.0	C18A—C19A—H19A	120.0
N1—C2B—C3B	117.1 (7)	C20A—C19A—C18A	120.0
H2BA—C2B—H2BB	107.3	C20A—C19A—H19A	120.0
C3B—C2B—H2BA	108.0	C15A—C20A—C23A	120.9 (4)
C3B—C2B—H2BB	108.0	C19A—C20A—C15A	120.0
C2A—C3A—H3AA	108.6	C19A—C20A—C23A	119.1 (4)
C2A—C3A—H3AB	108.6	C16B—C15B—N2B	120.4 (4)
C2A—C3A—C4A	114.5 (9)	C16B—C15B—C20B	120.0
H3AA—C3A—H3AB	107.6	C20B—C15B—N2B	119.2 (4)
C4A—C3A—H3AA	108.6	C15B—C16B—C21B	121.3 (5)
C4A—C3A—H3AB	108.6	C17B—C16B—C15B	120.0
C2B—C3B—H3BA	109.0	C17B—C16B—C21B	118.6 (5)
C2B—C3B—H3BB	109.0	C16B—C17B—H17B	120.0
H3BA—C3B—H3BB	107.8	C16B—C17B—C18B	120.0
C4B—C3B—C2B	112.8 (11)	C18B—C17B—H17B	120.0
C4B—C3B—H3BA	109.0	C17B—C18B—C19B	120.0
C4B—C3B—H3BB	109.0	C17B—C18B—C22B	120.4 (11)
C3A—C4A—H4AA	109.9	C19B—C18B—C22B	119.1 (11)
C3A—C4A—H4AB	109.9	C18B—C19B—H19B	120.0
C3A—C4A—C5A	108.8 (14)	C20B—C19B—C18B	120.0
H4AA—C4A—H4AB	108.3	C20B—C19B—H19B	120.0
C5A—C4A—H4AA	109.9	C15B—C20B—C23B	120.8 (4)
C5A—C4A—H4AB	109.9	C19B—C20B—C15B	120.0
C3B—C4B—H4BA	109.4	C19B—C20B—C23B	119.2 (4)
C3B—C4B—H4BB	109.4	C16A—C21A—H21A	109.5
C3B—C4B—C5B	111.0 (18)	C16A—C21A—H21B	109.5
H4BA—C4B—H4BB	108.0	C16A—C21A—H21C	109.5
C5B—C4B—H4BA	109.4	H21A—C21A—H21B	109.5
C5B—C4B—H4BB	109.4	H21A—C21A—H21C	109.5
N2A—C5A—C4A	110.9 (10)	H21B—C21A—H21C	109.5
N2A—C5A—H5AA	109.5	C16B—C21B—H21D	109.5
N2A—C5A—H5AB	109.5	C16B—C21B—H21E	109.5
C4A—C5A—H5AA	109.5	C16B—C21B—H21F	109.5
C4A—C5A—H5AB	109.5	H21D—C21B—H21E	109.5
H5AA—C5A—H5AB	108.0	H21D—C21B—H21F	109.5
N2B—C5B—C4B	110.8 (10)	H21E—C21B—H21F	109.5
N2B—C5B—H5BA	109.5	C18A—C22A—H22A	109.5
N2B—C5B—H5BB	109.5	C18A—C22A—H22B	109.5
C4B—C5B—H5BA	109.5	C18A—C22A—H22C	109.5
C4B—C5B—H5BB	109.5	H22A—C22A—H22B	109.5
H5BA—C5B—H5BB	108.1	H22A—C22A—H22C	109.5
C7—C6—N1	119.1 (3)	H22B—C22A—H22C	109.5
C11—C6—N1	119.6 (3)	C18B—C22B—H22D	109.5
C11—C6—C7	121.2 (3)	C18B—C22B—H22E	109.5
C6—C7—C12	121.2 (3)	C18B—C22B—H22F	109.5
C8—C7—C6	118.2 (3)	H22D—C22B—H22E	109.5
C8—C7—C12	120.6 (3)	H22D—C22B—H22F	109.5
C7—C8—H8	119.1	H22E—C22B—H22F	109.5
C9—C8—C7	121.7 (4)	C20A—C23A—H23A	109.5
C9—C8—H8	119.1	C20A—C23A—H23B	109.5
C8—C9—C13	120.0 (4)	C20A—C23A—H23C	109.5
C10—C9—C8	118.6 (3)	H23A—C23A—H23B	109.5
C10—C9—C13	121.3 (4)	H23A—C23A—H23C	109.5
C9—C10—H10	119.0	H23B—C23A—H23C	109.5
C9—C10—C11	122.1 (3)	C20B—C23B—H23D	109.5
C11—C10—H10	119.0	C20B—C23B—H23E	109.5
C6—C11—C14	120.8 (3)	C20B—C23B—H23F	109.5
C10—C11—C6	118.1 (3)	H23D—C23B—H23E	109.5
C10—C11—C14	121.2 (3)	H23D—C23B—H23F	109.5
C7—C12—H12A	109.5	H23E—C23B—H23F	109.5
N1—C2A—C3A—C4A	77.0 (12)	C6—N1—C1—N2B	−164.2 (4)
N1—C2B—C3B—C4B	−78.1 (14)	C6—N1—C2A—C3A	149.3 (5)
N1—C6—C7—C8	−176.8 (3)	C6—N1—C2B—C3B	−149.4 (6)
N1—C6—C7—C12	4.6 (5)	C6—C7—C8—C9	−0.2 (6)
N1—C6—C11—C10	177.3 (3)	C7—C6—C11—C10	0.8 (5)
N1—C6—C11—C14	−3.8 (4)	C7—C6—C11—C14	179.7 (3)
N2A—C15A—C16A—C17A	175.0 (5)	C7—C8—C9—C10	0.2 (6)
N2A—C15A—C16A—C21A	−7.6 (7)	C7—C8—C9—C13	−177.7 (4)
N2A—C15A—C20A—C19A	−174.9 (5)	C8—C9—C10—C11	0.4 (6)
N2A—C15A—C20A—C23A	3.2 (6)	C9—C10—C11—C6	−0.8 (6)
N2B—C15B—C16B—C17B	172.4 (5)	C9—C10—C11—C14	−179.8 (4)
N2B—C15B—C16B—C21B	−11.3 (7)	C11—C6—C7—C8	−0.3 (5)
N2B—C15B—C20B—C19B	−172.5 (5)	C11—C6—C7—C12	−178.9 (3)
N2B—C15B—C20B—C23B	6.8 (6)	C12—C7—C8—C9	178.5 (4)
C1—N1—C2A—C3A	−18.9 (9)	C13—C9—C10—C11	178.2 (4)
C1—N1—C2B—C3B	16.2 (10)	C15A—N2A—C1—S1	−21.2 (7)
C1—N1—C6—C7	−87.6 (4)	C15A—N2A—C1—N1	174.7 (4)
C1—N1—C6—C11	95.9 (3)	C15A—N2A—C5A—C4A	−102.8 (9)
C1—N2A—C5A—C4A	83.4 (10)	C15A—C16A—C17A—C18A	0.0
C1—N2A—C15A—C16A	105.9 (6)	C16A—C15A—C20A—C19A	0.0
C1—N2A—C15A—C20A	−79.2 (6)	C16A—C15A—C20A—C23A	178.1 (6)
C1—N2B—C5B—C4B	−83.3 (12)	C16A—C17A—C18A—C19A	0.0
C1—N2B—C15B—C16B	82.4 (6)	C16A—C17A—C18A—C22A	178.9 (12)
C1—N2B—C15B—C20B	−105.1 (6)	C17A—C18A—C19A—C20A	0.0
C2A—N1—C1—S1	165.3 (5)	C18A—C19A—C20A—C15A	0.0
C2A—N1—C1—N2A	−30.0 (7)	C18A—C19A—C20A—C23A	−178.2 (6)
C2A—N1—C6—C7	102.7 (5)	C20A—C15A—C16A—C17A	0.0
C2A—N1—C6—C11	−73.8 (5)	C20A—C15A—C16A—C21A	177.4 (6)
C2A—C3A—C4A—C5A	−32.3 (17)	C15B—N2B—C1—S1	25.8 (7)
C2B—N1—C1—S1	−167.1 (5)	C15B—N2B—C1—N1	−171.0 (4)
C2B—N1—C1—N2B	30.5 (7)	C15B—N2B—C5B—C4B	101.5 (11)
C2B—N1—C6—C7	78.7 (6)	C15B—C16B—C17B—C18B	0.0
C2B—N1—C6—C11	−97.8 (5)	C16B—C15B—C20B—C19B	0.0
C2B—C3B—C4B—C5B	38.1 (17)	C16B—C15B—C20B—C23B	179.2 (6)
C3A—C4A—C5A—N2A	−54.0 (15)	C16B—C17B—C18B—C19B	0.0
C3B—C4B—C5B—N2B	48.8 (16)	C16B—C17B—C18B—C22B	−172.0 (14)
C5A—N2A—C1—S1	152.4 (5)	C17B—C18B—C19B—C20B	0.0
C5A—N2A—C1—N1	−11.6 (7)	C18B—C19B—C20B—C15B	0.0
C5A—N2A—C15A—C16A	−68.4 (6)	C18B—C19B—C20B—C23B	−179.3 (6)
C5A—N2A—C15A—C20A	106.6 (6)	C20B—C15B—C16B—C17B	0.0
C5B—N2B—C1—S1	−149.0 (4)	C20B—C15B—C16B—C21B	176.3 (7)
C5B—N2B—C1—N1	14.1 (7)	C21A—C16A—C17A—C18A	−177.5 (6)
C5B—N2B—C15B—C16B	−102.5 (6)	C21B—C16B—C17B—C18B	−176.4 (7)
C5B—N2B—C15B—C20B	69.9 (6)	C22A—C18A—C19A—C20A	−178.9 (13)
C6—N1—C1—S1	−1.8 (4)	C22B—C18B—C19B—C20B	172.1 (14)
C6—N1—C1—N2A	162.8 (4)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4B—H4BB···S1^ii	0.99	2.97	3.72 (3)	133

Symmetry code: (ii) x−1, y, z.

(2SDiazMesSe_TIE)

Crystal data

C2I4·2(C23H30N2Se)	Z = 1
Mr = 1358.52	F(000) = 656
Triclinic, P1	Dx = 1.831 Mg m^−3
a = 7.9777 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.7334 (7) Å	Cell parameters from 9801 reflections
c = 15.0059 (9) Å	θ = 2.8–30.1°
α = 67.540 (2)°	µ = 4.04 mm^−1
β = 82.671 (2)°	T = 100 K
γ = 71.632 (2)°	Block, yellow
V = 1231.91 (13) Å^3	0.14 × 0.09 × 0.08 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	5668 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.037
φ and ω scans	θmax = 28.5°, θmin = 2.8°
Absorption correction: multi-scan SADABS v2016/2 (Bruker AXS Inc., 2017)	h = −10→10
Tmin = 0.636, Tmax = 0.746	k = −15→15
41652 measured reflections	l = −20→20
6224 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.065	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + 5.9779P] where P = (Fo^2 + 2Fc^2)/3
6224 reflections	(Δ/σ)max = 0.002
384 parameters	Δρmax = 3.78 e Å^−3
36 restraints	Δρmin = −3.88 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
I2	0.52402 (3)	1.04771 (2)	0.14671 (2)	0.02150 (6)
I1	0.44982 (3)	0.78503 (2)	0.11284 (2)	0.02499 (6)
C24A	0.4951 (5)	0.9695 (4)	0.0469 (4)	0.0152 (16)	0.739 (18)
C24B	0.5127 (16)	1.0483 (12)	0.0075 (10)	0.016 (5)	0.261 (18)
Se1	0.46079 (4)	0.49900 (3)	0.25928 (3)	0.02637 (9)
N1	0.2982 (4)	0.3119 (3)	0.36953 (19)	0.0189 (5)
C1	0.2882 (4)	0.4163 (3)	0.2874 (2)	0.0190 (6)
C6	0.4411 (4)	0.2682 (3)	0.4360 (2)	0.0178 (6)
C7	0.5904 (5)	0.1696 (3)	0.4302 (2)	0.0214 (6)
C8	0.7234 (5)	0.1261 (4)	0.4976 (3)	0.0350 (9)
H8	0.827293	0.060057	0.494484	0.042*
C9	0.7081 (6)	0.1765 (5)	0.5690 (3)	0.0437 (12)
C10	0.5575 (5)	0.2728 (4)	0.5731 (3)	0.0345 (9)
H10	0.546396	0.307171	0.622304	0.041*
C11	0.4219 (5)	0.3209 (3)	0.5074 (2)	0.0229 (7)
C12	0.6113 (6)	0.1143 (4)	0.3527 (3)	0.0323 (8)
H12A	0.530546	0.061625	0.365765	0.048*
H12B	0.733223	0.060545	0.351902	0.048*
H12C	0.583573	0.184540	0.289964	0.048*
C13	0.8552 (7)	0.1307 (8)	0.6399 (4)	0.080 (2)
H13A	0.926423	0.043102	0.646001	0.121*
H13B	0.804547	0.130663	0.702968	0.121*
H13C	0.930073	0.188512	0.616867	0.121*
C14	0.2616 (6)	0.4282 (4)	0.5116 (3)	0.0361 (9)
H14A	0.245129	0.499195	0.448879	0.054*
H14B	0.277470	0.458877	0.561310	0.054*
H14C	0.157439	0.396628	0.527304	0.054*
N2A	0.1868 (8)	0.4422 (6)	0.2128 (4)	0.0152 (11)	0.500 (6)
C2A	0.1969 (15)	0.2120 (11)	0.3982 (8)	0.023 (2)	0.500 (6)
H2AA	0.208196	0.157085	0.467544	0.027*	0.500 (6)
H2AB	0.229021	0.157815	0.358213	0.027*	0.500 (6)
C3A	−0.0290 (10)	0.3373 (8)	0.3669 (5)	0.0291 (17)	0.500 (6)
H3AA	−0.121922	0.308703	0.412453	0.035*	0.500 (6)
H3AB	−0.027231	0.421950	0.365446	0.035*	0.500 (6)
C4A	−0.053 (4)	0.341 (3)	0.267 (2)	0.026 (5)	0.500 (6)
H4AA	−0.087173	0.264299	0.273189	0.031*	0.500 (6)
H4AB	−0.149709	0.418682	0.234176	0.031*	0.500 (6)
C5A	0.1139 (9)	0.3435 (6)	0.2089 (5)	0.0190 (14)	0.500 (6)
H5AA	0.202288	0.257880	0.233738	0.023*	0.500 (6)
H5AB	0.089291	0.361647	0.140994	0.023*	0.500 (6)
C15A	0.1534 (8)	0.5616 (6)	0.1300 (4)	0.0140 (15)	0.500 (6)
C20A	0.2367 (8)	0.5615 (5)	0.0428 (4)	0.0163 (14)	0.500 (6)
C19A	0.1919 (8)	0.6715 (6)	−0.0399 (4)	0.0182 (16)	0.500 (6)
H19A	0.248786	0.671504	−0.099531	0.022*	0.500 (6)
C18A	0.0639 (11)	0.7816 (5)	−0.0354 (6)	0.019 (2)	0.500 (6)
C17A	−0.0193 (12)	0.7816 (6)	0.0518 (7)	0.0164 (19)	0.500 (6)
H17A	−0.106747	0.856795	0.054885	0.020*	0.500 (6)
C16A	0.0255 (10)	0.6716 (8)	0.1345 (5)	0.0188 (19)	0.500 (6)
C21A	−0.0627 (10)	0.6761 (9)	0.2302 (6)	0.0246 (16)	0.500 (6)
H21A	−0.147530	0.625878	0.248861	0.037*	0.500 (6)
H21B	−0.124464	0.765683	0.223014	0.037*	0.500 (6)
H21C	0.027488	0.639497	0.280168	0.037*	0.500 (6)
C22A	0.008 (5)	0.898 (4)	−0.125 (3)	0.026 (6)	0.500 (6)
H22A	−0.115660	0.912770	−0.139171	0.039*	0.500 (6)
H22B	0.082863	0.884893	−0.179458	0.039*	0.500 (6)
H22C	0.018955	0.973824	−0.115858	0.039*	0.500 (6)
C23A	0.3771 (10)	0.4420 (6)	0.0359 (5)	0.0248 (16)	0.500 (6)
H23A	0.455496	0.403102	0.091619	0.037*	0.500 (6)
H23B	0.446276	0.466403	−0.023551	0.037*	0.500 (6)
H23C	0.319987	0.379686	0.035148	0.037*	0.500 (6)
N2B	0.1246 (8)	0.4698 (6)	0.2431 (5)	0.0160 (11)	0.500 (6)
C2B	0.1515 (17)	0.2524 (12)	0.4093 (10)	0.031 (3)	0.500 (6)
H2BA	0.043504	0.315495	0.421041	0.037*	0.500 (6)
H2BB	0.186152	0.176997	0.469784	0.037*	0.500 (6)
C3B	0.1210 (9)	0.2056 (6)	0.3134 (5)	0.0241 (15)	0.500 (6)
H3BA	0.217912	0.210713	0.265060	0.029*	0.500 (6)
H3BB	0.103629	0.118906	0.336998	0.029*	0.500 (6)
C4B	−0.047 (4)	0.313 (2)	0.277 (2)	0.023 (4)	0.500 (6)
H4BA	−0.149038	0.286611	0.315026	0.027*	0.500 (6)
H4BB	−0.064961	0.328216	0.208772	0.027*	0.500 (6)
C5B	−0.0392 (8)	0.4358 (6)	0.2857 (5)	0.0219 (15)	0.500 (6)
H5BA	−0.142592	0.507542	0.252882	0.026*	0.500 (6)
H5BB	−0.046321	0.425082	0.354662	0.026*	0.500 (6)
C15B	0.1046 (8)	0.5749 (6)	0.1520 (4)	0.0153 (15)	0.500 (6)
C20B	0.1629 (8)	0.5533 (4)	0.0669 (4)	0.0185 (15)	0.500 (6)
C19B	0.1305 (8)	0.6555 (6)	−0.0211 (4)	0.0206 (17)	0.500 (6)
H19B	0.170351	0.640787	−0.079260	0.025*	0.500 (6)
C18B	0.0396 (11)	0.7793 (5)	−0.0241 (5)	0.020 (2)	0.500 (6)
C17B	−0.0187 (13)	0.8009 (5)	0.0610 (7)	0.0169 (19)	0.500 (6)
H17B	−0.080802	0.885492	0.058983	0.020*	0.500 (6)
C16B	0.0138 (11)	0.6987 (7)	0.1491 (5)	0.0147 (16)	0.500 (6)
C21B	−0.0453 (11)	0.7264 (8)	0.2400 (6)	0.0246 (16)	0.500 (6)
H21D	−0.156545	0.705581	0.262892	0.037*	0.500 (6)
H21E	−0.062823	0.817888	0.226751	0.037*	0.500 (6)
H21F	0.045148	0.673798	0.289613	0.037*	0.500 (6)
C22B	0.002 (5)	0.893 (4)	−0.122 (3)	0.027 (6)	0.500 (6)
H22D	−0.072774	0.878149	−0.160565	0.041*	0.500 (6)
H22E	0.114216	0.899048	−0.155862	0.041*	0.500 (6)
H22F	−0.057808	0.972978	−0.110526	0.041*	0.500 (6)
C23B	0.2599 (10)	0.4181 (7)	0.0675 (5)	0.0245 (16)	0.500 (6)
H23D	0.355536	0.377251	0.114681	0.037*	0.500 (6)
H23E	0.309487	0.423903	0.003253	0.037*	0.500 (6)
H23F	0.177031	0.366483	0.084972	0.037*	0.500 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I2	0.02356 (11)	0.02208 (11)	0.02296 (11)	−0.00485 (8)	−0.00281 (8)	−0.01318 (8)
I1	0.01757 (10)	0.01457 (10)	0.03631 (13)	−0.00495 (8)	−0.00103 (9)	−0.00179 (9)
C24A	0.0143 (19)	0.014 (3)	0.021 (3)	−0.0028 (15)	−0.0025 (15)	−0.011 (2)
C24B	0.017 (6)	0.013 (8)	0.016 (7)	−0.006 (4)	0.004 (4)	−0.001 (5)
Se1	0.01676 (15)	0.02421 (17)	0.02493 (17)	−0.00778 (13)	−0.00538 (13)	0.00829 (13)
N1	0.0176 (13)	0.0197 (13)	0.0159 (13)	−0.0066 (11)	−0.0020 (10)	−0.0011 (10)
C1	0.0223 (16)	0.0130 (13)	0.0187 (15)	−0.0027 (12)	−0.0062 (12)	−0.0027 (12)
C6	0.0197 (15)	0.0161 (14)	0.0121 (13)	−0.0049 (12)	−0.0019 (11)	0.0008 (11)
C7	0.0261 (17)	0.0154 (14)	0.0165 (15)	−0.0039 (13)	0.0018 (12)	−0.0016 (12)
C8	0.0257 (19)	0.038 (2)	0.0176 (17)	0.0072 (16)	−0.0023 (14)	0.0031 (15)
C9	0.027 (2)	0.074 (3)	0.0139 (17)	−0.006 (2)	−0.0049 (14)	−0.0040 (19)
C10	0.036 (2)	0.054 (3)	0.0157 (16)	−0.0159 (19)	0.0007 (15)	−0.0126 (17)
C11	0.0243 (17)	0.0242 (16)	0.0156 (15)	−0.0052 (13)	0.0039 (12)	−0.0051 (13)
C12	0.039 (2)	0.0231 (17)	0.0304 (19)	−0.0024 (16)	0.0031 (16)	−0.0119 (15)
C13	0.039 (3)	0.148 (6)	0.027 (2)	−0.002 (3)	−0.013 (2)	−0.019 (3)
C14	0.041 (2)	0.036 (2)	0.0271 (19)	−0.0005 (18)	0.0049 (17)	−0.0168 (17)
N2A	0.015 (3)	0.014 (3)	0.017 (3)	−0.004 (2)	0.000 (2)	−0.006 (2)
C2A	0.020 (5)	0.029 (6)	0.016 (4)	−0.013 (4)	0.000 (3)	0.000 (4)
C3A	0.025 (4)	0.039 (4)	0.028 (4)	−0.016 (3)	0.014 (3)	−0.016 (3)
C4A	0.016 (5)	0.028 (12)	0.032 (8)	−0.006 (7)	0.003 (5)	−0.010 (8)
C5A	0.020 (3)	0.019 (3)	0.020 (3)	−0.007 (2)	0.001 (2)	−0.008 (2)
C15A	0.015 (4)	0.017 (3)	0.010 (3)	−0.005 (3)	−0.002 (3)	−0.003 (3)
C20A	0.014 (3)	0.019 (3)	0.018 (3)	−0.003 (3)	−0.005 (3)	−0.009 (3)
C19A	0.015 (4)	0.021 (3)	0.015 (3)	−0.003 (3)	−0.005 (3)	−0.003 (3)
C18A	0.023 (4)	0.024 (4)	0.014 (3)	−0.011 (3)	−0.004 (3)	−0.007 (3)
C17A	0.012 (4)	0.014 (3)	0.022 (4)	0.000 (3)	−0.004 (3)	−0.007 (3)
C16A	0.018 (4)	0.026 (5)	0.017 (4)	−0.008 (3)	0.000 (3)	−0.012 (3)
C21A	0.024 (4)	0.023 (4)	0.023 (4)	0.003 (3)	−0.001 (3)	−0.011 (3)
C22A	0.026 (9)	0.030 (9)	0.013 (7)	−0.003 (7)	−0.010 (7)	0.000 (7)
C23A	0.029 (4)	0.019 (3)	0.021 (3)	−0.001 (3)	0.004 (3)	−0.007 (3)
N2B	0.013 (3)	0.012 (2)	0.018 (3)	0.000 (2)	−0.003 (2)	−0.002 (2)
C2B	0.029 (6)	0.035 (7)	0.028 (5)	−0.012 (5)	0.000 (4)	−0.007 (5)
C3B	0.024 (3)	0.019 (3)	0.030 (4)	−0.009 (3)	−0.004 (3)	−0.006 (3)
C4B	0.027 (7)	0.018 (9)	0.025 (6)	−0.015 (6)	−0.003 (4)	−0.003 (5)
C5B	0.012 (3)	0.020 (3)	0.027 (3)	−0.003 (2)	−0.001 (2)	−0.003 (3)
C15B	0.011 (3)	0.012 (3)	0.019 (3)	−0.001 (2)	−0.004 (2)	−0.003 (2)
C20B	0.012 (3)	0.014 (3)	0.027 (4)	−0.003 (3)	−0.007 (3)	−0.004 (3)
C19B	0.019 (4)	0.030 (4)	0.016 (3)	−0.007 (3)	0.000 (3)	−0.011 (3)
C18B	0.013 (3)	0.013 (4)	0.025 (4)	0.002 (3)	−0.010 (3)	0.001 (3)
C17B	0.016 (3)	0.016 (3)	0.019 (4)	−0.004 (3)	−0.006 (3)	−0.005 (3)
C16B	0.014 (3)	0.015 (3)	0.017 (3)	−0.003 (2)	−0.007 (2)	−0.006 (2)
C21B	0.030 (4)	0.017 (4)	0.021 (4)	0.003 (3)	−0.003 (3)	−0.007 (3)
C22B	0.023 (8)	0.024 (8)	0.027 (10)	−0.005 (7)	−0.002 (7)	−0.002 (7)
C23B	0.027 (4)	0.020 (3)	0.027 (4)	−0.004 (3)	−0.003 (3)	−0.011 (3)

Geometric parameters (Å, º)

I2—C24A	2.099 (5)	C19A—H19A	0.9500
I2—C24B	2.100 (14)	C19A—C18A	1.3900
I1—C24A	2.135 (5)	C18A—C17A	1.3900
I1—C24B^i	2.170 (13)	C18A—C22A	1.50 (4)
C24A—C24A^i	1.319 (10)	C17A—H17A	0.9500
C24B—C24B^i	1.31 (3)	C17A—C16A	1.3900
Se1—C1	1.843 (3)	C16A—C21A	1.529 (9)
N1—C1	1.355 (4)	C21A—H21A	0.9800
N1—C6	1.445 (4)	C21A—H21B	0.9800
N1—C2A	1.528 (12)	C21A—H21C	0.9800
N1—C2B	1.494 (14)	C22A—H22A	0.9800
C1—N2A	1.348 (6)	C22A—H22B	0.9800
C1—N2B	1.388 (6)	C22A—H22C	0.9800
C6—C7	1.395 (4)	C23A—H23A	0.9800
C6—C11	1.400 (5)	C23A—H23B	0.9800
C7—C8	1.395 (5)	C23A—H23C	0.9800
C7—C12	1.504 (5)	N2B—C5B	1.482 (9)
C8—H8	0.9500	N2B—C15B	1.434 (8)
C8—C9	1.384 (6)	C2B—H2BA	0.9900
C9—C10	1.380 (6)	C2B—H2BB	0.9900
C9—C13	1.512 (6)	C2B—C3B	1.791 (15)
C10—H10	0.9500	C3B—H3BA	0.9900
C10—C11	1.387 (5)	C3B—H3BB	0.9900
C11—C14	1.500 (5)	C3B—C4B	1.51 (3)
C12—H12A	0.9800	C4B—H4BA	0.9900
C12—H12B	0.9800	C4B—H4BB	0.9900
C12—H12C	0.9800	C4B—C5B	1.52 (3)
C13—H13A	0.9800	C5B—H5BA	0.9900
C13—H13B	0.9800	C5B—H5BB	0.9900
C13—H13C	0.9800	C15B—C20B	1.3900
C14—H14A	0.9800	C15B—C16B	1.3900
C14—H14B	0.9800	C20B—C19B	1.3900
C14—H14C	0.9800	C20B—C23B	1.527 (8)
N2A—C5A	1.472 (8)	C19B—H19B	0.9500
N2A—C15A	1.448 (7)	C19B—C18B	1.3900
C2A—H2AA	0.9900	C18B—C17B	1.3900
C2A—H2AB	0.9900	C18B—C22B	1.54 (4)
C2A—C3A	1.910 (14)	C17B—H17B	0.9500
C3A—H3AA	0.9900	C17B—C16B	1.3900
C3A—H3AB	0.9900	C16B—C21B	1.506 (9)
C3A—C4A	1.51 (3)	C21B—H21D	0.9800
C4A—H4AA	0.9900	C21B—H21E	0.9800
C4A—H4AB	0.9900	C21B—H21F	0.9800
C4A—C5A	1.50 (3)	C22B—H22D	0.9800
C5A—H5AA	0.9900	C22B—H22E	0.9800
C5A—H5AB	0.9900	C22B—H22F	0.9800
C15A—C20A	1.3900	C23B—H23D	0.9800
C15A—C16A	1.3900	C23B—H23E	0.9800
C20A—C19A	1.3900	C23B—H23F	0.9800
C20A—C23A	1.525 (8)
C24A—I1—C24B^i	24.9 (4)	C17A—C18A—C19A	120.0
I2—C24A—I1	113.4 (2)	C17A—C18A—C22A	119.5 (15)
C24A^i—C24A—I2	122.1 (5)	C18A—C17A—H17A	120.0
C24A^i—C24A—I1	124.5 (5)	C18A—C17A—C16A	120.0
I2—C24B—I1^i	117.1 (6)	C16A—C17A—H17A	120.0
C24B^i—C24B—I2	122.3 (13)	C15A—C16A—C21A	121.1 (6)
C1—N1—C6	119.9 (3)	C17A—C16A—C15A	120.0
C1—N1—C2A	129.2 (5)	C17A—C16A—C21A	118.9 (6)
C1—N1—C2B	124.5 (6)	C16A—C21A—H21A	109.5
C6—N1—C2A	109.9 (5)	C16A—C21A—H21B	109.5
C6—N1—C2B	114.3 (6)	C16A—C21A—H21C	109.5
N1—C1—Se1	119.7 (2)	H21A—C21A—H21B	109.5
N1—C1—N2B	114.5 (4)	H21A—C21A—H21C	109.5
N2A—C1—Se1	115.8 (3)	H21B—C21A—H21C	109.5
N2A—C1—N1	122.1 (4)	C18A—C22A—H22A	109.5
N2B—C1—Se1	123.9 (3)	C18A—C22A—H22B	109.5
C7—C6—N1	118.9 (3)	C18A—C22A—H22C	109.5
C7—C6—C11	121.9 (3)	H22A—C22A—H22B	109.5
C11—C6—N1	119.1 (3)	H22A—C22A—H22C	109.5
C6—C7—C8	117.6 (3)	H22B—C22A—H22C	109.5
C6—C7—C12	121.7 (3)	C20A—C23A—H23A	109.5
C8—C7—C12	120.7 (3)	C20A—C23A—H23B	109.5
C7—C8—H8	119.1	C20A—C23A—H23C	109.5
C9—C8—C7	121.8 (4)	H23A—C23A—H23B	109.5
C9—C8—H8	119.1	H23A—C23A—H23C	109.5
C8—C9—C13	121.2 (5)	H23B—C23A—H23C	109.5
C10—C9—C8	119.0 (4)	C1—N2B—C5B	125.5 (5)
C10—C9—C13	119.8 (5)	C1—N2B—C15B	118.6 (5)
C9—C10—H10	119.1	C15B—N2B—C5B	115.7 (5)
C9—C10—C11	121.7 (4)	N1—C2B—H2BA	111.5
C11—C10—H10	119.1	N1—C2B—H2BB	111.5
C6—C11—C14	121.1 (3)	N1—C2B—C3B	101.2 (8)
C10—C11—C6	118.0 (3)	H2BA—C2B—H2BB	109.3
C10—C11—C14	120.8 (3)	C3B—C2B—H2BA	111.5
C7—C12—H12A	109.5	C3B—C2B—H2BB	111.5
C7—C12—H12B	109.5	C2B—C3B—H3BA	112.7
C7—C12—H12C	109.5	C2B—C3B—H3BB	112.7
H12A—C12—H12B	109.5	H3BA—C3B—H3BB	110.2
H12A—C12—H12C	109.5	C4B—C3B—C2B	95.2 (13)
H12B—C12—H12C	109.5	C4B—C3B—H3BA	112.7
C9—C13—H13A	109.5	C4B—C3B—H3BB	112.7
C9—C13—H13B	109.5	C3B—C4B—H4BA	109.5
C9—C13—H13C	109.5	C3B—C4B—H4BB	109.5
H13A—C13—H13B	109.5	C3B—C4B—C5B	111 (2)
H13A—C13—H13C	109.5	H4BA—C4B—H4BB	108.1
H13B—C13—H13C	109.5	C5B—C4B—H4BA	109.5
C11—C14—H14A	109.5	C5B—C4B—H4BB	109.5
C11—C14—H14B	109.5	N2B—C5B—C4B	112.6 (13)
C11—C14—H14C	109.5	N2B—C5B—H5BA	109.1
H14A—C14—H14B	109.5	N2B—C5B—H5BB	109.1
H14A—C14—H14C	109.5	C4B—C5B—H5BA	109.1
H14B—C14—H14C	109.5	C4B—C5B—H5BB	109.1
C1—N2A—C5A	120.3 (5)	H5BA—C5B—H5BB	107.8
C1—N2A—C15A	123.3 (5)	C20B—C15B—N2B	121.0 (5)
C15A—N2A—C5A	116.2 (5)	C20B—C15B—C16B	120.0
N1—C2A—H2AA	112.9	C16B—C15B—N2B	118.8 (5)
N1—C2A—H2AB	112.9	C15B—C20B—C23B	121.3 (5)
N1—C2A—C3A	94.4 (6)	C19B—C20B—C15B	120.0
H2AA—C2A—H2AB	110.3	C19B—C20B—C23B	118.7 (5)
C3A—C2A—H2AA	112.9	C20B—C19B—H19B	120.0
C3A—C2A—H2AB	112.9	C20B—C19B—C18B	120.0
C2A—C3A—H3AA	111.7	C18B—C19B—H19B	120.0
C2A—C3A—H3AB	111.7	C19B—C18B—C22B	120.1 (15)
H3AA—C3A—H3AB	109.5	C17B—C18B—C19B	120.0
C4A—C3A—C2A	100.1 (12)	C17B—C18B—C22B	119.9 (15)
C4A—C3A—H3AA	111.7	C18B—C17B—H17B	120.0
C4A—C3A—H3AB	111.7	C18B—C17B—C16B	120.0
C3A—C4A—H4AA	109.5	C16B—C17B—H17B	120.0
C3A—C4A—H4AB	109.5	C15B—C16B—C21B	121.4 (6)
H4AA—C4A—H4AB	108.1	C17B—C16B—C15B	120.0
C5A—C4A—C3A	111 (2)	C17B—C16B—C21B	118.5 (6)
C5A—C4A—H4AA	109.5	C16B—C21B—H21D	109.5
C5A—C4A—H4AB	109.5	C16B—C21B—H21E	109.5
N2A—C5A—C4A	111.4 (13)	C16B—C21B—H21F	109.5
N2A—C5A—H5AA	109.4	H21D—C21B—H21E	109.5
N2A—C5A—H5AB	109.4	H21D—C21B—H21F	109.5
C4A—C5A—H5AA	109.4	H21E—C21B—H21F	109.5
C4A—C5A—H5AB	109.4	C18B—C22B—H22D	109.5
H5AA—C5A—H5AB	108.0	C18B—C22B—H22E	109.5
C20A—C15A—N2A	119.2 (5)	C18B—C22B—H22F	109.5
C20A—C15A—C16A	120.0	H22D—C22B—H22E	109.5
C16A—C15A—N2A	120.5 (5)	H22D—C22B—H22F	109.5
C15A—C20A—C23A	121.0 (4)	H22E—C22B—H22F	109.5
C19A—C20A—C15A	120.0	C20B—C23B—H23D	109.5
C19A—C20A—C23A	119.0 (4)	C20B—C23B—H23E	109.5
C20A—C19A—H19A	120.0	C20B—C23B—H23F	109.5
C20A—C19A—C18A	120.0	H23D—C23B—H23E	109.5
C18A—C19A—H19A	120.0	H23D—C23B—H23F	109.5
C19A—C18A—C22A	120.4 (15)	H23E—C23B—H23F	109.5
Se1—C1—N2A—C5A	148.5 (5)	C2A—N1—C1—N2A	−4.3 (8)
Se1—C1—N2A—C15A	−26.9 (7)	C2A—N1—C6—C7	74.0 (5)
Se1—C1—N2B—C5B	−154.1 (5)	C2A—N1—C6—C11	−102.6 (5)
Se1—C1—N2B—C15B	20.1 (8)	C2A—C3A—C4A—C5A	−43.8 (18)
N1—C1—N2A—C5A	−13.7 (8)	C3A—C4A—C5A—N2A	−49.0 (19)
N1—C1—N2A—C15A	170.9 (5)	C5A—N2A—C15A—C20A	−69.5 (7)
N1—C1—N2B—C5B	10.3 (8)	C5A—N2A—C15A—C16A	103.4 (7)
N1—C1—N2B—C15B	−175.6 (5)	C15A—N2A—C5A—C4A	−101.0 (13)
N1—C6—C7—C8	−177.7 (3)	C15A—C20A—C19A—C18A	0.0
N1—C6—C7—C12	4.1 (5)	C20A—C15A—C16A—C17A	0.0
N1—C6—C11—C10	177.0 (3)	C20A—C15A—C16A—C21A	−177.5 (8)
N1—C6—C11—C14	−4.4 (5)	C20A—C19A—C18A—C17A	0.0
N1—C2B—C3B—C4B	−105.1 (13)	C20A—C19A—C18A—C22A	−176.7 (18)
C1—N1—C6—C7	−95.7 (4)	C19A—C18A—C17A—C16A	0.0
C1—N1—C6—C11	87.7 (4)	C18A—C17A—C16A—C15A	0.0
C1—N1—C2A—C3A	−49.8 (7)	C18A—C17A—C16A—C21A	177.5 (8)
C1—N1—C2B—C3B	61.2 (8)	C16A—C15A—C20A—C19A	0.0
C1—N2A—C5A—C4A	83.2 (14)	C16A—C15A—C20A—C23A	−179.9 (7)
C1—N2A—C15A—C20A	106.1 (6)	C22A—C18A—C17A—C16A	176.7 (18)
C1—N2A—C15A—C16A	−81.0 (7)	C23A—C20A—C19A—C18A	179.9 (7)
C1—N2B—C5B—C4B	−80.4 (14)	N2B—C15B—C20B—C19B	175.2 (6)
C1—N2B—C15B—C20B	79.4 (7)	N2B—C15B—C20B—C23B	−3.6 (7)
C1—N2B—C15B—C16B	−105.3 (6)	N2B—C15B—C16B—C17B	−175.3 (6)
C6—N1—C1—Se1	1.7 (4)	N2B—C15B—C16B—C21B	7.1 (8)
C6—N1—C1—N2A	163.2 (4)	C2B—N1—C1—Se1	167.9 (6)
C6—N1—C1—N2B	−163.4 (4)	C2B—N1—C1—N2B	2.8 (8)
C6—N1—C2A—C3A	141.7 (4)	C2B—N1—C6—C7	96.8 (6)
C6—N1—C2B—C3B	−132.0 (5)	C2B—N1—C6—C11	−79.8 (6)
C6—C7—C8—C9	1.1 (6)	C2B—C3B—C4B—C5B	36.5 (18)
C7—C6—C11—C10	0.5 (5)	C3B—C4B—C5B—N2B	51 (2)
C7—C6—C11—C14	179.1 (3)	C5B—N2B—C15B—C20B	−105.9 (7)
C7—C8—C9—C10	−0.3 (7)	C5B—N2B—C15B—C16B	69.4 (7)
C7—C8—C9—C13	−178.5 (5)	C15B—N2B—C5B—C4B	105.2 (13)
C8—C9—C10—C11	−0.4 (7)	C15B—C20B—C19B—C18B	0.0
C9—C10—C11—C6	0.3 (6)	C20B—C15B—C16B—C17B	0.0
C9—C10—C11—C14	−178.3 (4)	C20B—C15B—C16B—C21B	−177.6 (8)
C11—C6—C7—C8	−1.1 (5)	C20B—C19B—C18B—C17B	0.0
C11—C6—C7—C12	−179.4 (3)	C20B—C19B—C18B—C22B	−179.6 (18)
C12—C7—C8—C9	179.3 (4)	C19B—C18B—C17B—C16B	0.0
C13—C9—C10—C11	177.8 (5)	C18B—C17B—C16B—C15B	0.0
N2A—C15A—C20A—C19A	173.0 (5)	C18B—C17B—C16B—C21B	177.7 (8)
N2A—C15A—C20A—C23A	−6.9 (7)	C16B—C15B—C20B—C19B	0.0
N2A—C15A—C16A—C17A	−172.9 (6)	C16B—C15B—C20B—C23B	−178.8 (7)
N2A—C15A—C16A—C21A	9.7 (8)	C22B—C18B—C17B—C16B	179.6 (18)
C2A—N1—C1—Se1	−165.7 (6)	C23B—C20B—C19B—C18B	178.8 (7)

Symmetry code: (i) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4A—H4AB···Se1^ii	0.99	2.97	3.73 (3)	134

Symmetry code: (ii) x−1, y, z.