2,2′-{2-[(E)-3-Phenyl­prop-2-enyl]-2,3-di­hydro-1H-isoindol-1,3-diyl­idene}­dimalono­nitrile, a π-deficient system for π...π (1:1) stacking investigations

The title compound, C₂₃H₁₃N₅, derived from cinnamyl alcohol and 2,2′-(isoindolin-1,3-diyl­idene)­bis­propane­di­nitrile, is a heterocyclic TCNQ analogue of interest as an electron-deficient component in charge-transfer complexes. A small perturbation of the four C—C[triple bond]N angles from linearity is observed, which are in the range 173.41 (18)–176.3 (2)°; the C[triple bond]N bond lengths are in the range 1.144 (2)–1.146 (2) Å. The terminal phenyl group is oriented at an angle of 77.17 (6)° to the C₄N ring and the C=C bond is short, 1.319 (2) Å. There are no classical hydrogen bonds, although intramolecular C—H...N and intermolecular C—H...π(arene) interactions influence the crystal-structure packing.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.112
• Data-to-parameter ratio = 13.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C(6A)  -   C(7A)  =       1.44 Ang.

PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C(6A)  -   C(8A)  =       1.42 Ang.

PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C(6B)  -   C(7B)  =       1.43 Ang.

PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C(6B)  -   C(8B)  =       1.43 Ang.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 4 Alert Level C = Please check

---

S1. Comment

Organic conductors are currently an important research area in materials chemistry (Martin et al., 1997; Yamashita & Tomura, 1998), with special interest in the interaction of π-deficient and π-excessive materials in 1:1 complexes, e.g. TCNQ/TTF, where TCNQ is tetracyanoquinodimethane and TTF is tetrathiafulvalene.

The bond lengths and angles in the heterocyclic ring of the title compound, (I) (Fig. 1), are similar to those reported previously in related systems (McNab et al., 1997; Brady et al., 1998; Gallagher & Murphy, 1999; Brady & Gallagher, 2000). For TCNQ (tetracyanoquinodimethane) systems (280 examples), the average exocyclic Csp²═Csp² and Csp²—Csp¹ bond lengths are 1.392 (17) and 1.427 (10) Å, respectively; thus, in (I), the C6A—C7A, C6A—C8A and C6B—C7B and C6B—C8B bond lengths in the range 1.425 (3)–1.436 (3) Å are normal (Orpen et al., 1994). The four nitrile C≡N values are from 1.144 (2) to 1.146 (2) Å, which compare with the average C≡N dimension from the literature, 1.144 (8) Å (Orpen et al., 1994). The exocyclic indolinyl ring C═C bond lengths are 1.372 (2) and 1.374 (2) Å, which are longer than typical double bonds. The four remaining exocyclic indolinyl cyano C—C bond lengths are in the range 1.425 (3)–1.436 (3) Å and similar to previously reported values. The angles which the C(C≡N)₂ groups make with the C₄N ring are 7.01 (10) (C6A) and 2.33 (10)° (C6B), demonstrating a small twist from planarity about the C4—C6(A/B) bonds.

The hydrogen bonding in (I) is dominated by intramolecular C—H···N interactions and close contacts (details in Table 3). There are two intramolecular C(arene)—H···π(C≡N) interactions with C12—H12···N2A and C15—H15···N2B C···N distances of 3.390 (3) and 3.390 (2) Å, respectively. A C1—H1B···N3A intramolecular contact is present [C1···N3A 3.401 (2) Å and C—H···N 139°]. A C—H···π(arene) interaction is also present, C14—H14···Cg1, where Cg1 is the centroid of {C21–C26}ⁱ [symmetry code: (i) 1/2 - x, 1/2 + y, 1/2 - z; details in Table 3]. The closest C14···C26ⁱ contact distance is 3.696 (2) Å with a C14—H14···Cg1 angle of 121°.

S2. Experimental

The title compound was prepared by the 5 d reaction under argon of DIAD (diisopropylazodicarboxylate) (0.37 g, 1.9 mmol), triphenylphosphine (0.49 g, 1.9 mmol), 2,2'-(isoindolin-1,3-diylidene)bispropanedinitrile (0.25 g, 1.9 mmol) (French patent No. 1537299), cinnamyl alcohol (0.25 g, 1.9 mmol) in 40 ml tetrahydrofuran. 2,2'-(Cinnamylisoindolin-1,3-diylidene)bispropanedinitrile, (I), was isolated as an orange crystalline material after column chromatography. (m.p. 469–471 K uncorrected). IR (KBr, cm^-1): 3049, 2372, 2335, 2224, 1563, 1465, 1407, 1228, 1146, 1109, 983, 775, 723; UV-Vis (CH₃CN) λ_max(ε): 552 (5250), 459 (6667), 414 (38333), 392 (39167), 249 (47083) nm; ¹H NMR (400 MHz, δ, CDCl₃): 8.75 (m, 2H, aromatic), 7.85 (m, 2H, aromatic), 7.37 (m, 2H, aromatic), 7.30 (m, 3H, aromatic), 6.50 (d, J = 16 Hz, 1H), 6.25 (m, 1H), 5.50 (m, 2H); ¹³C NMR (δC, CDCl₃): 156.8, 135.0, 134.8, 134.0, 130.9, 128.8, 128.7, 126.9, 126.0, 120.5, 113.1, 112.3, 62.1, 47.8.

S3. Refinement

In (I), all H atoms bound to C atoms were treated as riding, with SHELXL97 (Sheldrick, 1997) defaults for C—H lengths and with U_iso(H) = 1.5U_eq(C) for methylene H atoms and 1.2U_eq(C) for the remainder. Examination of the structure with PLATON (Spek, 1998) showed that there were no solvent-accessible voids in the crystal lattice.

Computing details

Data collection: XSCANS (Bruker, 1994); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: NRCVAX96 (Gabe et al., 1989) and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 1998); software used to prepare material for publication: NRCVAX96, SHELXL97 and WORDPERFECT macro PREP8 (Ferguson, 1998).

Figures

Fig. 1. A view of (I) with the atomic numbering scheme. Displacement ellipsoids are depicted at the 30% probability level.

2,2'-{2-[(E)-3-phenylprop-2-enyl]-2,3-dihydro-1H-isoindol-1,3-diylidene}- dimalononitrile

Crystal data

C23H13N5	Dx = 1.309 Mg m^−3
Mr = 359.38	Melting point: 470 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 14.3872 (18) Å	Cell parameters from 33 reflections
b = 8.2696 (10) Å	θ = 7.1–20.5°
c = 16.1442 (15) Å	µ = 0.08 mm^−1
β = 108.327 (7)°	T = 296 K
V = 1823.4 (4) Å^3	Block, orange
Z = 4	0.43 × 0.38 × 0.28 mm
F(000) = 744

Data collection

Bruker P4 diffractometer	Rint = 0.012
Radiation source: X-ray tube	θmax = 25.5°, θmin = 2.7°
Graphite monochromator	h = −1→17
ω–2θ scans	k = −1→10
4331 measured reflections	l = −19→18
3367 independent reflections	3 standard reflections every 197 reflections
2630 reflections with I > 2σ(I)	intensity decay: 2%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0529P)^2 + 0.3178P] where P = (Fo^2 + 2Fc^2)/3
3367 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

Experimental. The phenyl ring carbon atoms C23 and C24 have large displacement parameters, however, there is no evidence for disorder in this aromatic ring system.

Geometry. Selected Geometrical Data Ex-PLATON (Spek, 1998) =================================================

Specific hydrogen bonds (with e.s.d.'s except fixed and riding H) =========================================================================== Interaction D—H H···A D···A D—H···A (symmetry operator) =========================================================================== C1—H1B···N3A 0.97 2.61 3.401 (2) 139.0 C12—H12···N2A 0.93 2.59 3.390 (3) 144.9 C15—H15···N2B 0.93 2.59 3.390 (2) 144.7 C3—H3···N1 0.93 2.52 2.887 (2) 103.6 C12—H12···C7A 0.93 2.45 3.019 (3) 119.2 C15—H15···C7B 0.93 2.46 3.015 (2) 118.7

# A test for the pi(arene) interactions C14—H14···C21_$1 0.93 3.01 3.758 (2) 139.1 C14—H14···C22_$1 0.93 3.38 4.278 (3) 162.9 ** No suitable H-bond found for C14···C23_$1 = 4.681 (3) A ** ** No suitable H-bond found for C14···C24_$1 = 4.623 (3) A ** C14—H14···C25_$1 0.93 3.59 4.155 (3) 121.6 C14—H14···C26_$1 0.93 3.13 3.696 (2) 120.9

Mean plane data ex-SHELXL97 for compound (I) #################################################################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

2.2436(0.0097)x + 2.9253(0.0053)y + 13.3422(0.0062)z = 4.6210(0.0046)

* -0.0103 (0.0008) N1 * 0.0087 (0.0008) C4 * 0.0074 (0.0008) C5 * -0.0039 (0.0009) C11 * -0.0019 (0.0009) C16 - 0.2010 (0.0037) N2A 0.3218 (0.0039) N3A 0.1300 (0.0037) N2B 0.0531 (0.0036) N3B

Rms deviation of fitted atoms = 0.0071

2.0759(0.0091)x + 2.8298(0.0049)y + 13.4969(0.0058)z = 4.5230(0.0049)

Angle to previous plane (with approximate e.s.d.) = 1.01 (8)

* -0.0039 (0.0010) C11 * 0.0015 (0.0011) C12 * 0.0013 (0.0012) C13 * -0.0017 (0.0012) C14 * -0.0007 (0.0011) C15 * 0.0036 (0.0010) C16 - 0.0473 (0.0033) C1 1.2661 (0.0038) C2 2.4434 (0.0035) C3 0.0297 (0.0024) N1

Rms deviation of fitted atoms = 0.0024

-9.6646(0.0099)x + 6.0973(0.0052)y + 4.5061(0.0133)z = 6.6496(0.0070)

Angle to previous plane (with approximate e.s.d.) = 77.19 (6)

* -0.0069 (0.0013) C21 * 0.0009 (0.0015) C22 * 0.0057 (0.0018) C23 * -0.0063 (0.0017) C24 * 0.0002 (0.0015) C25 * 0.0063 (0.0013) C26 - 0.3313 (0.0046) C1 - 0.1496 (0.0036) C2 - 0.0684 (0.0029) C3 - 0.5732 (0.0048) N1

Rms deviation of fitted atoms = 0.0052

2.2436(0.0097)x + 2.9253(0.0053)y + 13.3422(0.0062)z = 4.6210(0.0046)

Angle to previous plane (with approximate e.s.d.) = 77.17 (6)

* -0.0103 (0.0008) N1 * 0.0087 (0.0008) C4 * 0.0074 (0.0008) C5 * -0.0039 (0.0009) C11 * -0.0019 (0.0009) C16 - 0.2010 (0.0037) N2A 0.3218 (0.0039) N3A 0.1300 (0.0037) N2B 0.0531 (0.0036) N3B

Rms deviation of fitted atoms = 0.0071

2.0759(0.0091)x + 2.8298(0.0049)y + 13.4969(0.0058)z = 4.5230(0.0049)

Angle to previous plane (with approximate e.s.d.) = 1.01 (8)

* -0.0039 (0.0010) C11 * 0.0015 (0.0011) C12 * 0.0013 (0.0012) C13 * -0.0017 (0.0012) C14 * -0.0007 (0.0011) C15 * 0.0036 (0.0010) C16 - 0.0473 (0.0033) C1 1.2661 (0.0038) C2 2.4434 (0.0035) C3 0.0297 (0.0024) N1

Rms deviation of fitted atoms = 0.0024

-9.3535(0.0348)x + 6.2714(0.0167)y + 2.5779(0.0290)z = 6.0796(0.0067)

Angle to previous plane (with approximate e.s.d.) = 83.00 (12)

* 0.0000 (0.0000) C1 * 0.0000 (0.0000) C2 * 0.0000 (0.0000) C3

Rms deviation of fitted atoms = 0.0000

-9.6646(0.0099)x + 6.0973(0.0052)y + 4.5061(0.0133)z = 6.6496(0.0070)

Angle to previous plane (with approximate e.s.d.) = 7.0 (3)

* -0.0069 (0.0013) C21 * 0.0009 (0.0015) C22 * 0.0057 (0.0018) C23 * -0.0063 (0.0017) C24 * 0.0002 (0.0015) C25 * 0.0063 (0.0013) C26 - 0.3313 (0.0046) C1 - 0.1496 (0.0036) C2 - 0.0684 (0.0029) C3 - 0.5732 (0.0048) N1

Rms deviation of fitted atoms = 0.0052

3.4727(0.0172)x + 3.5183(0.0076)y + 12.1414(0.0074)z = 5.0679(0.0114)

Angle to previous plane (with approximate e.s.d.) = 77.65 (8)

* -0.0017 (0.0009) C6A * 0.0152 (0.0014) C7A * -0.0113 (0.0016) C8A * -0.0086 (0.0008) N2A * 0.0064 (0.0009) N3A 0.0001 (0.0035) C4 - 0.0447 (0.0064) C5

Rms deviation of fitted atoms = 0.0098

2.2436(0.0097)x + 2.9253(0.0053)y + 13.3422(0.0062)z = 4.6210(0.0046)

Angle to previous plane (with approximate e.s.d.) = 7.01 (10)

* -0.0103 (0.0008) N1 * 0.0087 (0.0008) C4 * 0.0074 (0.0008) C5 * -0.0039 (0.0009) C11 * -0.0019 (0.0009) C16 - 0.2010 (0.0037) N2A 0.3218 (0.0039) N3A 0.1300 (0.0037) N2B 0.0531 (0.0036) N3B

Rms deviation of fitted atoms = 0.0071

1.8392(0.0096)x + 3.1608(0.0091)y + 13.3766(0.0058)z = 4.7690(0.0036)

Angle to previous plane (with approximate e.s.d.) = 2.33 (10)

* 0.0000 (0.0008) C6B * -0.0070 (0.0015) C7B * 0.0068 (0.0013) C8B * 0.0040 (0.0008) N2B * -0.0038 (0.0007) N3B 0.1146 (0.0058) C4 0.0217 (0.0032) C5

Rms deviation of fitted atoms = 0.0050

2.0759(0.0091)x + 2.8298(0.0049)y + 13.4969(0.0058)z = 4.5230(0.0049)

Angle to previous plane (with approximate e.s.d.) = 2.59 (9)

* -0.0039 (0.0010) C11 * 0.0015 (0.0011) C12 * 0.0013 (0.0012) C13 * -0.0017 (0.0012) C14 * -0.0007 (0.0011) C15 * 0.0036 (0.0010) C16 - 0.0473 (0.0033) C1 1.2661 (0.0038) C2 2.4434 (0.0035) C3 0.0297 (0.0024) N1

Rms deviation of fitted atoms = 0.0024

3.4727(0.0172)x + 3.5183(0.0076)y + 12.1414(0.0074)z = 5.0679(0.0114)

Angle to previous plane (with approximate e.s.d.) = 8.01 (10)

* -0.0017 (0.0009) C6A * 0.0152 (0.0014) C7A * -0.0113 (0.0016) C8A * -0.0086 (0.0008) N2A * 0.0064 (0.0009) N3A 0.0001 (0.0035) C4 - 0.0447 (0.0064) C5

Rms deviation of fitted atoms = 0.0098

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

	x	y	z	Uiso*/Ueq
N1	−0.00647 (8)	0.87131 (15)	0.15563 (8)	0.0367 (3)
N2A	−0.11664 (14)	1.4060 (2)	0.04262 (12)	0.0788 (6)
N3A	−0.24231 (13)	1.0780 (3)	0.17486 (15)	0.0907 (6)
N2B	0.28853 (13)	0.5619 (2)	0.18438 (12)	0.0732 (5)
N3B	0.04444 (12)	0.42660 (19)	0.24932 (11)	0.0620 (4)
C1	−0.07949 (11)	0.7765 (2)	0.18104 (10)	0.0437 (4)
C2	−0.05987 (12)	0.7661 (2)	0.27751 (11)	0.0470 (4)
C3	0.00903 (12)	0.8440 (2)	0.33779 (11)	0.0458 (4)
C4	−0.01804 (11)	1.02862 (18)	0.12450 (9)	0.0380 (3)
C5	0.08302 (10)	0.80880 (18)	0.15561 (9)	0.0349 (3)
C11	0.06880 (11)	1.06855 (18)	0.10020 (9)	0.0380 (3)
C12	0.09685 (13)	1.2087 (2)	0.06691 (10)	0.0479 (4)
C13	0.18639 (13)	1.2119 (2)	0.05246 (11)	0.0539 (5)
C14	0.24716 (13)	1.0783 (2)	0.07089 (11)	0.0524 (4)
C15	0.22077 (11)	0.9379 (2)	0.10446 (10)	0.0443 (4)
C16	0.13076 (10)	0.93386 (18)	0.11947 (9)	0.0363 (3)
C6A	−0.09671 (11)	1.1275 (2)	0.11819 (10)	0.0465 (4)
C7A	−0.10479 (13)	1.2830 (2)	0.07685 (12)	0.0559 (5)
C8A	−0.17655 (13)	1.0939 (2)	0.14997 (13)	0.0598 (5)
C6B	0.11864 (11)	0.65823 (18)	0.18467 (9)	0.0390 (4)
C7B	0.21323 (13)	0.6091 (2)	0.18276 (11)	0.0483 (4)
C8B	0.07334 (12)	0.5348 (2)	0.22056 (10)	0.0441 (4)
C21	0.03457 (13)	0.8243 (2)	0.43290 (11)	0.0488 (4)
C22	−0.01487 (18)	0.7189 (2)	0.47126 (13)	0.0697 (6)
C23	0.0135 (2)	0.6989 (3)	0.56013 (15)	0.0909 (8)
C24	0.0913 (2)	0.7812 (3)	0.61307 (15)	0.0896 (8)
C25	0.14131 (17)	0.8881 (3)	0.57716 (14)	0.0791 (7)
C26	0.11258 (13)	0.9101 (3)	0.48711 (12)	0.0601 (5)
H1A	−0.0814	0.6679	0.1578	0.052*
H1B	−0.1435	0.8246	0.1547	0.052*
H2	−0.1002	0.6980	0.2969	0.056*
H3	0.0453	0.9194	0.3181	0.055*
H12	0.0560	1.2987	0.0546	0.057*
H13	0.2060	1.3048	0.0301	0.065*
H14	0.3071	1.0829	0.0605	0.063*
H15	0.2621	0.8486	0.1167	0.053*
H22	−0.0681	0.6608	0.4362	0.084*
H23	−0.0210	0.6282	0.5844	0.109*
H24	0.1107	0.7655	0.6731	0.108*
H25	0.1943	0.9455	0.6131	0.095*
H26	0.1462	0.9831	0.4632	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0329 (6)	0.0395 (7)	0.0373 (6)	0.0023 (5)	0.0102 (5)	0.0005 (5)
N2A	0.0846 (13)	0.0526 (10)	0.0805 (12)	0.0195 (9)	−0.0009 (10)	0.0042 (9)
N3A	0.0570 (11)	0.1029 (16)	0.1203 (17)	0.0166 (11)	0.0396 (11)	−0.0124 (13)
N2B	0.0652 (11)	0.0815 (12)	0.0802 (12)	0.0323 (10)	0.0333 (9)	0.0223 (10)
N3B	0.0682 (10)	0.0506 (9)	0.0639 (10)	−0.0038 (8)	0.0162 (8)	0.0115 (8)
C1	0.0340 (8)	0.0465 (9)	0.0508 (9)	−0.0028 (7)	0.0133 (7)	−0.0014 (7)
C2	0.0429 (9)	0.0499 (10)	0.0543 (10)	−0.0040 (8)	0.0241 (8)	0.0002 (8)
C3	0.0461 (9)	0.0452 (9)	0.0516 (9)	−0.0007 (7)	0.0232 (8)	−0.0014 (8)
C4	0.0376 (8)	0.0377 (8)	0.0331 (7)	0.0013 (6)	0.0030 (6)	−0.0037 (6)
C5	0.0330 (7)	0.0390 (8)	0.0302 (7)	0.0013 (6)	0.0063 (6)	−0.0030 (6)
C11	0.0375 (8)	0.0391 (8)	0.0325 (7)	−0.0016 (6)	0.0042 (6)	−0.0024 (6)
C12	0.0539 (10)	0.0373 (9)	0.0462 (9)	−0.0018 (7)	0.0070 (7)	0.0019 (7)
C13	0.0580 (11)	0.0481 (10)	0.0537 (10)	−0.0152 (9)	0.0148 (8)	0.0051 (8)
C14	0.0446 (9)	0.0603 (11)	0.0528 (10)	−0.0107 (8)	0.0160 (8)	0.0012 (8)
C15	0.0381 (8)	0.0501 (9)	0.0439 (8)	−0.0003 (7)	0.0116 (7)	0.0009 (7)
C16	0.0351 (7)	0.0397 (8)	0.0305 (7)	−0.0014 (6)	0.0051 (6)	−0.0015 (6)
C6A	0.0405 (8)	0.0460 (9)	0.0460 (9)	0.0071 (7)	0.0035 (7)	−0.0070 (7)
C7A	0.0512 (10)	0.0479 (11)	0.0550 (10)	0.0125 (8)	−0.0028 (8)	−0.0075 (9)
C8A	0.0430 (10)	0.0642 (12)	0.0672 (12)	0.0152 (9)	0.0102 (9)	−0.0109 (9)
C6B	0.0393 (8)	0.0404 (8)	0.0358 (7)	0.0043 (7)	0.0097 (6)	0.0017 (6)
C7B	0.0517 (10)	0.0477 (9)	0.0469 (9)	0.0126 (8)	0.0173 (8)	0.0090 (8)
C8B	0.0469 (9)	0.0416 (9)	0.0400 (8)	0.0052 (7)	0.0080 (7)	0.0020 (7)
C21	0.0536 (10)	0.0469 (9)	0.0495 (9)	0.0109 (8)	0.0212 (8)	−0.0031 (8)
C22	0.0976 (16)	0.0588 (12)	0.0567 (11)	−0.0052 (11)	0.0299 (11)	0.0051 (9)
C23	0.148 (2)	0.0689 (15)	0.0624 (14)	−0.0006 (16)	0.0430 (16)	0.0082 (12)
C24	0.137 (2)	0.0792 (16)	0.0507 (12)	0.0340 (17)	0.0264 (14)	0.0085 (12)
C25	0.0769 (14)	0.0912 (17)	0.0586 (12)	0.0252 (13)	0.0061 (11)	−0.0192 (12)
C26	0.0550 (11)	0.0695 (13)	0.0572 (11)	0.0104 (10)	0.0197 (9)	−0.0117 (9)

Geometric parameters (Å, º)

N1—C1	1.469 (2)	C11—C16	1.399 (2)
N1—C4	1.386 (2)	C12—C13	1.380 (2)
N1—C5	1.388 (2)	C13—C14	1.382 (3)
N2A—C7A	1.145 (2)	C14—C15	1.384 (2)
N3A—C8A	1.146 (2)	C15—C16	1.391 (2)
N2B—C7B	1.144 (2)	C6A—C8A	1.425 (3)
N3B—C8B	1.145 (2)	C6A—C7A	1.436 (3)
C1—C2	1.495 (2)	C6B—C8B	1.428 (2)
C2—C3	1.319 (2)	C6B—C7B	1.430 (2)
C3—C21	1.471 (2)	C21—C26	1.382 (3)
C4—C6A	1.374 (2)	C21—C22	1.388 (3)
C4—C11	1.460 (2)	C22—C23	1.373 (3)
C5—C6B	1.372 (2)	C23—C24	1.359 (4)
C5—C16	1.461 (2)	C24—C25	1.377 (4)
C11—C12	1.389 (2)	C25—C26	1.393 (3)
C1—N1—C4	125.99 (12)	C5—C16—C11	107.80 (13)
C1—N1—C5	123.11 (12)	C5—C16—C15	131.85 (14)
C4—N1—C5	110.82 (12)	C4—C6A—C7A	120.78 (16)
N1—C1—C2	113.84 (13)	C4—C6A—C8A	126.56 (16)
C1—C2—C3	126.34 (15)	C8A—C6A—C7A	112.66 (15)
C2—C3—C21	126.82 (16)	N2A—C7A—C6A	176.3 (2)
N1—C4—C6A	126.02 (15)	N3A—C8A—C6A	175.3 (2)
N1—C5—C6B	125.80 (14)	C5—C6B—C7B	120.42 (14)
N1—C4—C11	107.12 (12)	C5—C6B—C8B	128.19 (14)
C6A—C4—C11	126.86 (15)	C8B—C6B—C7B	111.37 (14)
C6B—C5—C16	127.39 (13)	N2B—C7B—C6B	175.81 (18)
N1—C5—C16	106.81 (12)	N3B—C8B—C6B	173.41 (18)
C4—C11—C12	132.04 (14)	C3—C21—C22	122.70 (17)
C4—C11—C16	107.42 (13)	C3—C21—C26	119.39 (17)
C12—C11—C16	120.50 (14)	C22—C21—C26	117.89 (18)
C11—C12—C13	118.79 (16)	C21—C22—C23	121.1 (2)
C12—C13—C14	120.64 (16)	C22—C23—C24	120.8 (2)
C13—C14—C15	121.46 (16)	C23—C24—C25	119.5 (2)
C14—C15—C16	118.26 (16)	C24—C25—C26	120.0 (2)
C11—C16—C15	120.35 (14)	C21—C26—C25	120.6 (2)
C4—N1—C1—C2	−102.16 (17)	C4—C11—C16—C5	0.19 (15)
C5—N1—C1—C2	81.50 (18)	C4—C11—C16—C15	−178.86 (13)
N1—C1—C2—C3	6.6 (2)	C6B—C5—C16—C11	−178.82 (14)
C1—C2—C3—C21	−174.28 (16)	C6B—C5—C16—C15	0.1 (3)
C1—N1—C4—C6A	5.3 (2)	N1—C5—C16—C11	0.90 (15)
C5—N1—C4—C6A	−178.02 (14)	N1—C5—C16—C15	179.80 (15)
C1—N1—C4—C11	−174.88 (13)	N1—C4—C6A—C7A	−173.84 (14)
C5—N1—C4—C11	1.84 (15)	N1—C4—C6A—C8A	6.6 (3)
C1—N1—C5—C6B	−5.2 (2)	C11—C4—C6A—C7A	6.3 (2)
C4—N1—C5—C6B	178.01 (13)	C11—C4—C6A—C8A	−173.25 (15)
C1—N1—C5—C16	175.11 (12)	N1—C5—C6B—C7B	−178.75 (14)
C4—N1—C5—C16	−1.72 (15)	N1—C5—C6B—C8B	0.0 (2)
N1—C4—C11—C12	−178.93 (15)	C16—C5—C6B—C7B	0.9 (2)
N1—C4—C11—C16	−1.22 (15)	C16—C5—C6B—C8B	179.65 (14)
C6A—C4—C11—C12	0.9 (3)	C2—C3—C21—C22	−1.5 (3)
C6A—C4—C11—C16	178.64 (14)	C2—C3—C21—C26	176.66 (17)
C4—C11—C12—C13	178.09 (15)	C26—C21—C22—C23	−0.8 (3)
C16—C11—C12—C13	0.6 (2)	C3—C21—C22—C23	177.4 (2)
C12—C11—C16—C5	178.22 (13)	C3—C21—C26—C25	−176.94 (17)
C12—C11—C16—C15	−0.8 (2)	C21—C22—C23—C24	−0.4 (4)
C11—C12—C13—C14	−0.1 (2)	C22—C23—C24—C25	1.1 (4)
C12—C13—C14—C15	−0.2 (3)	C23—C24—C25—C26	−0.6 (3)
C13—C14—C15—C16	0.0 (2)	C22—C21—C26—C25	1.3 (3)
C14—C15—C16—C11	0.5 (2)	C24—C25—C26—C21	−0.6 (3)
C14—C15—C16—C5	−178.28 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···N3A	0.97	2.61	3.401 (2)	139
C12—H12···N2A	0.93	2.59	3.390 (3)	145
C12—H12···C7A	0.93	2.45	3.019 (3)	119
C15—H15···N2B	0.93	2.59	3.390 (2)	145
C15—H15···C7B	0.93	2.46	3.015 (2)	119
C14—H14···Cg1^i	0.93	3.20	3.984 (2)	143

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.