Download citation
Download citation
link to html
The halogen bond (XB) is a topical noncovalent interaction of rapidly increasing importance. The XB employs a `soft' donor atom in comparison to the `hard' proton of the hydrogen bond (HB). This difference has led to the hypothesis that XBs can form more favorable interactions with `soft' bases than HBs. While computational studies have supported this suggestion, solution and solid-state data are lacking. Here, XB soft–soft complementarity is investigated with a bidentate receptor that shows similar associations with neutral carbonyls and heavy chalcogen analogs. The solution speciation and XB soft–soft complementarity is supported by four crystal structures containing neutral and anionic soft Lewis bases.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520617001809/xm5006sup1.cif
Contains datablocks dmfotf, arc_scn_meoh, arc_scn_ccl2, arc_3i

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520617001809/xm5006dmfotfsup2.hkl
Contains datablock dmfotf

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520617001809/xm5006arc_scn_meohsup3.hkl
Contains datablock arc_scn_meoh

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520617001809/xm5006arc_scn_ccl2sup4.hkl
Contains datablock arc_scn_ccl2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520617001809/xm5006arc_3isup5.hkl
Contains datablock arc_3i

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520617001809/xm5006sup6.pdf
Supporting figures and tables

CCDC references: 1520140; 1520141; 1520142; 1520143

Computing details top

Data collection: APEX2 (Bruker-AXS, 2007) for dmfotf. Cell refinement: SAINT v8.34A (Bruker, 2013) for dmfotf, arc_scn_ccl2, arc_3i. Data reduction: SAINT v8.34A (Bruker, 2013) for dmfotf, arc_scn_ccl2, arc_3i. For all compounds, program(s) used to solve structure: ShelXT (Sheldrick, 2015); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

(dmfotf) top
Crystal data top
C22H16I2N2·C3H7NO·2(CF3O3S)Dx = 1.877 Mg m3
Mr = 933.40Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcnCell parameters from 9865 reflections
a = 22.4519 (12) Åθ = 3.3–30.5°
b = 18.1915 (9) ŵ = 2.11 mm1
c = 8.0879 (4) ÅT = 100 K
V = 3303.4 (3) Å3Rod, yellow
Z = 40.5 × 0.05 × 0.03 mm
F(000) = 1816
Data collection top
Bruker D8 VENTURE Duo
diffractometer
3786 independent reflections
Radiation source: sealed tube, fine-focus3280 reflections with I > 2σ(I)
TRIUMPH graphite monochromatorRint = 0.075
Detector resolution: 10.5 pixels mm-1θmax = 27.5°, θmin = 2.9°
ω and φ scansh = 2929
Absorption correction: multi-scan
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0947 before and 0.0667 after correction. The Ratio of minimum to maximum transmission is 0.7268. The λ/2 correction factor is 0.00150.
k = 2323
Tmin = 0.193, Tmax = 0.266l = 1010
83218 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.31 w = 1/[σ2(Fo2) + (0.0214P)2 + 28.357P]
where P = (Fo2 + 2Fc2)/3
3786 reflections(Δ/σ)max = 0.001
239 parametersΔρmax = 0.92 e Å3
0 restraintsΔρmin = 1.29 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
I10.40238 (2)0.34468 (2)0.61791 (5)0.02618 (13)
N10.2514 (2)0.3718 (3)0.3026 (6)0.0221 (11)
C10.2955 (3)0.3450 (4)0.3973 (7)0.0243 (12)
H10.29890.29340.41260.029*
C20.3358 (2)0.3908 (3)0.4723 (7)0.0193 (12)
C30.3311 (3)0.4677 (3)0.4468 (7)0.0209 (12)
C40.2844 (3)0.4925 (4)0.3475 (7)0.0234 (13)
H40.27980.54370.32860.028*
C50.2450 (3)0.4445 (4)0.2769 (8)0.0244 (13)
H50.21330.46240.21020.029*
C60.3729 (3)0.5163 (3)0.5191 (8)0.0209 (13)
C70.4099 (3)0.5543 (3)0.5826 (8)0.0245 (13)
C80.4550 (3)0.5952 (3)0.6666 (8)0.0221 (13)
C90.4556 (3)0.6723 (3)0.6679 (9)0.0293 (15)
H90.42520.69870.61190.035*
C100.50000.7102 (5)0.75000.034 (2)
H100.50000.76240.75000.041*
C110.50000.5567 (5)0.75000.0217 (18)
H110.50000.50450.75000.026*
C120.2076 (3)0.3197 (4)0.2310 (9)0.0308 (15)
H12A0.22430.26990.23250.046*
H12B0.19880.33400.11680.046*
H12C0.17090.32090.29650.046*
O1'0.4913 (11)0.2600 (5)0.775 (4)0.033 (5)0.5
N1'0.4887 (7)0.1358 (6)0.769 (3)0.025 (4)0.5
C1'0.4714 (6)0.2013 (7)0.8205 (18)0.029 (3)0.5
H1'0.44050.20260.90080.035*0.5
C2'0.4606 (8)0.0689 (9)0.828 (2)0.044 (4)0.5
H2'A0.43560.08020.92420.066*0.5
H2'B0.49130.03330.85980.066*0.5
H2'C0.43580.04800.74010.066*0.5
C3'0.5378 (9)0.1289 (11)0.654 (3)0.050 (5)0.5
H3'A0.54950.17780.61500.075*0.5
H3'B0.52560.09860.55990.075*0.5
H3'C0.57170.10570.71000.075*0.5
S1'0.17263 (7)0.35761 (8)0.7049 (2)0.0225 (3)
F1'0.1258 (2)0.4429 (3)0.9293 (6)0.0469 (11)
F2'0.0639 (2)0.4024 (4)0.7473 (7)0.0686 (17)
F3'0.0953 (2)0.3309 (3)0.9385 (6)0.0631 (16)
O2'0.2193 (2)0.3403 (3)0.8228 (6)0.0335 (11)
O3'0.1508 (3)0.2955 (3)0.6158 (7)0.0453 (14)
O4'0.1839 (2)0.4218 (3)0.6077 (6)0.0326 (11)
C4'0.1111 (3)0.3848 (5)0.8367 (9)0.0358 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0252 (2)0.0252 (2)0.0282 (2)0.00057 (18)0.01022 (17)0.00706 (19)
N10.019 (2)0.031 (3)0.017 (2)0.005 (2)0.001 (2)0.002 (2)
C10.028 (3)0.027 (3)0.018 (3)0.005 (3)0.000 (2)0.003 (3)
C20.015 (3)0.027 (3)0.016 (3)0.004 (2)0.002 (2)0.002 (2)
C30.019 (3)0.025 (3)0.019 (3)0.003 (2)0.005 (2)0.004 (2)
C40.023 (3)0.026 (3)0.021 (3)0.009 (3)0.006 (3)0.004 (3)
C50.019 (3)0.034 (3)0.020 (3)0.010 (3)0.002 (3)0.007 (3)
C60.015 (3)0.024 (3)0.024 (3)0.003 (2)0.007 (2)0.006 (3)
C70.017 (3)0.026 (3)0.030 (3)0.005 (2)0.008 (3)0.006 (3)
C80.015 (3)0.019 (3)0.032 (3)0.002 (2)0.010 (2)0.002 (3)
C90.025 (3)0.015 (3)0.048 (4)0.006 (2)0.009 (3)0.007 (3)
C100.029 (5)0.009 (4)0.064 (7)0.0000.020 (5)0.000
C110.020 (4)0.019 (4)0.027 (5)0.0000.008 (4)0.000
C120.026 (3)0.036 (4)0.030 (3)0.009 (3)0.012 (3)0.008 (3)
O1'0.024 (14)0.022 (4)0.053 (17)0.001 (4)0.018 (9)0.006 (6)
N1'0.024 (14)0.023 (5)0.029 (12)0.006 (5)0.005 (9)0.003 (5)
C1'0.029 (7)0.030 (7)0.029 (7)0.007 (6)0.010 (6)0.007 (6)
C2'0.053 (10)0.031 (8)0.048 (10)0.007 (7)0.002 (8)0.008 (7)
C3'0.045 (11)0.049 (11)0.056 (14)0.000 (8)0.013 (9)0.004 (9)
S1'0.0230 (7)0.0171 (7)0.0274 (8)0.0066 (6)0.0004 (6)0.0019 (6)
F1'0.041 (3)0.056 (3)0.044 (3)0.002 (2)0.004 (2)0.011 (2)
F2'0.025 (2)0.130 (5)0.051 (3)0.013 (3)0.006 (2)0.001 (3)
F3'0.058 (3)0.089 (4)0.042 (3)0.042 (3)0.016 (2)0.010 (3)
O2'0.024 (2)0.034 (3)0.043 (3)0.005 (2)0.001 (2)0.001 (2)
O3'0.055 (3)0.037 (3)0.044 (3)0.021 (3)0.002 (3)0.007 (3)
O4'0.039 (3)0.029 (2)0.030 (2)0.006 (2)0.006 (2)0.009 (2)
C4'0.020 (3)0.062 (5)0.026 (3)0.011 (3)0.001 (3)0.003 (3)
Geometric parameters (Å, º) top
I1—C22.080 (6)C12—H12A0.9800
N1—C11.344 (8)C12—H12B0.9800
N1—C51.347 (8)C12—H12C0.9800
N1—C121.482 (8)O1'—C1'1.215 (17)
C1—H10.9500N1'—C1'1.321 (17)
C1—C21.371 (9)N1'—C2'1.452 (18)
C2—C31.418 (8)N1'—C3'1.45 (2)
C3—C41.395 (8)C1'—H1'0.9500
C3—C61.417 (9)C2'—H2'A0.9800
C4—H40.9500C2'—H2'B0.9800
C4—C51.367 (9)C2'—H2'C0.9800
C5—H50.9500C3'—H3'A0.9800
C6—C71.196 (9)C3'—H3'B0.9800
C7—C81.429 (9)C3'—H3'C0.9800
C8—C91.403 (8)S1'—O2'1.452 (5)
C8—C111.402 (7)S1'—O3'1.427 (5)
C9—H90.9500S1'—O4'1.430 (5)
C9—C101.382 (8)S1'—C4'1.814 (7)
C10—C9i1.382 (8)F1'—C4'1.337 (9)
C10—H100.9500F2'—C4'1.321 (8)
C11—C8i1.402 (7)F3'—C4'1.327 (9)
C11—H110.9500
C1—N1—C5121.5 (6)N1—C12—H12C109.5
C1—N1—C12118.7 (5)H12A—C12—H12B109.5
C5—N1—C12119.8 (5)H12A—C12—H12C109.5
N1—C1—H1119.4H12B—C12—H12C109.5
N1—C1—C2121.2 (6)C1'—N1'—C2'121.6 (13)
C2—C1—H1119.4C1'—N1'—C3'120.3 (14)
C1—C2—I1118.6 (4)C3'—N1'—C2'118.1 (14)
C1—C2—C3119.1 (5)O1'—C1'—N1'126.0 (15)
C3—C2—I1122.3 (4)O1'—C1'—H1'117.0
C4—C3—C2117.3 (6)N1'—C1'—H1'117.0
C4—C3—C6122.3 (6)N1'—C2'—H2'A109.5
C6—C3—C2120.4 (5)N1'—C2'—H2'B109.5
C3—C4—H4119.3N1'—C2'—H2'C109.5
C5—C4—C3121.3 (6)H2'A—C2'—H2'B109.5
C5—C4—H4119.3H2'A—C2'—H2'C109.5
N1—C5—C4119.6 (6)H2'B—C2'—H2'C109.5
N1—C5—H5120.2N1'—C3'—H3'A109.5
C4—C5—H5120.2N1'—C3'—H3'B109.5
C7—C6—C3176.6 (6)N1'—C3'—H3'C109.5
C6—C7—C8175.8 (7)H3'A—C3'—H3'B109.5
C9—C8—C7122.1 (6)H3'A—C3'—H3'C109.5
C11—C8—C7118.6 (6)H3'B—C3'—H3'C109.5
C11—C8—C9119.3 (6)O2'—S1'—C4'102.9 (3)
C8—C9—H9119.7O3'—S1'—O2'114.1 (3)
C10—C9—C8120.6 (6)O3'—S1'—O4'115.4 (3)
C10—C9—H9119.7O3'—S1'—C4'104.6 (3)
C9i—C10—C9120.2 (8)O4'—S1'—O2'114.2 (3)
C9—C10—H10119.9O4'—S1'—C4'103.6 (3)
C9i—C10—H10119.9F1'—C4'—S1'110.9 (5)
C8i—C11—C8120.1 (8)F2'—C4'—S1'110.8 (5)
C8—C11—H11120.0F2'—C4'—F1'108.2 (7)
C8i—C11—H11120.0F2'—C4'—F3'107.8 (6)
N1—C12—H12A109.5F3'—C4'—S1'111.5 (6)
N1—C12—H12B109.5F3'—C4'—F1'107.6 (6)
I1—C2—C3—C4179.7 (4)C11—C8—C9—C100.2 (9)
I1—C2—C3—C61.0 (8)C12—N1—C1—C2177.2 (6)
N1—C1—C2—I1179.7 (4)C12—N1—C5—C4177.9 (6)
N1—C1—C2—C31.0 (9)C2'—N1'—C1'—O1'178 (3)
C1—N1—C5—C40.5 (9)C3'—N1'—C1'—O1'4 (4)
C1—C2—C3—C41.0 (9)O2'—S1'—C4'—F1'60.1 (6)
C1—C2—C3—C6178.3 (6)O2'—S1'—C4'—F2'179.8 (6)
C2—C3—C4—C50.4 (9)O2'—S1'—C4'—F3'59.7 (5)
C3—C4—C5—N10.4 (9)O3'—S1'—C4'—F1'179.5 (5)
C5—N1—C1—C20.2 (9)O3'—S1'—C4'—F2'60.4 (7)
C6—C3—C4—C5179.0 (6)O3'—S1'—C4'—F3'59.7 (6)
C7—C8—C9—C10179.8 (5)O4'—S1'—C4'—F1'59.2 (6)
C7—C8—C11—C8i179.9 (6)O4'—S1'—C4'—F2'61.0 (6)
C8—C9—C10—C9i0.1 (4)O4'—S1'—C4'—F3'179.0 (5)
C9—C8—C11—C8i0.1 (4)
Symmetry code: (i) x+1, y, z+3/2.
(arc_scn_meoh) top
Crystal data top
C22H16I2N2·2(CNS)·CH4OZ = 2
Mr = 710.37F(000) = 688
Triclinic, P1Dx = 1.786 Mg m3
a = 9.1203 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.3562 (14) ÅCell parameters from 9947 reflections
c = 13.9355 (18) Åθ = 3.1–25.8°
α = 77.294 (4)°µ = 2.56 mm1
β = 71.958 (4)°T = 100 K
γ = 77.390 (4)°Block, yellow
V = 1321.1 (3) Å30.15 × 0.1 × 0.05 mm
Data collection top
Bruker D8 VENTURE Duo
diffractometer
5062 independent reflections
Radiation source: sealed tube, fine-focus4063 reflections with I > 2σ(I)
TRIUMPH graphite monochromatorRint = 0.076
Detector resolution: 10.5 pixels mm-1θmax = 25.9°, θmin = 3.1°
ω and φ scansh = 1111
Absorption correction: multi-scan
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1059 before and 0.0892 after correction. The Ratio of minimum to maximum transmission is 0.7584. The λ/2 correction factor is 0.00150.
k = 1313
Tmin = 0.252, Tmax = 0.332l = 1717
41885 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: mixed
wR(F2) = 0.157H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.1006P)2 + 3.7977P]
where P = (Fo2 + 2Fc2)/3
5062 reflections(Δ/σ)max < 0.001
314 parametersΔρmax = 3.37 e Å3
0 restraintsΔρmin = 2.02 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
I10.74484 (5)0.06812 (4)0.53431 (3)0.02508 (17)
I20.18193 (5)0.42188 (4)0.15915 (3)0.02235 (17)
N10.8299 (6)0.3768 (5)0.6273 (4)0.0224 (12)
N20.0568 (6)0.8122 (5)0.1752 (4)0.0226 (12)
C10.8148 (8)0.2634 (6)0.6212 (5)0.0218 (14)
H10.84930.19490.66650.026*
C20.7497 (8)0.2463 (6)0.5495 (5)0.0222 (14)
C30.6951 (7)0.3483 (6)0.4842 (5)0.0210 (14)
C40.7125 (8)0.4645 (6)0.4943 (5)0.0232 (14)
H40.67850.53520.45070.028*
C50.7788 (8)0.4758 (6)0.5671 (5)0.0258 (15)
H50.78830.55460.57470.031*
C60.6284 (7)0.3325 (6)0.4093 (5)0.0210 (14)
C70.5732 (8)0.3131 (6)0.3478 (5)0.0225 (14)
C80.5095 (7)0.2850 (6)0.2752 (5)0.0216 (14)
C90.5106 (8)0.1631 (6)0.2697 (5)0.0256 (15)
H90.55440.09850.31390.031*
C100.4480 (8)0.1370 (6)0.2001 (5)0.0276 (15)
H100.44970.05430.19600.033*
C110.3822 (8)0.2312 (6)0.1358 (5)0.0257 (15)
H110.33730.21260.08900.031*
C120.4470 (7)0.3800 (6)0.2093 (5)0.0209 (14)
H120.44870.46260.21180.025*
C130.3821 (8)0.3530 (6)0.1400 (5)0.0245 (14)
C140.3161 (7)0.4494 (6)0.0743 (5)0.0169 (13)
C150.2586 (8)0.5313 (6)0.0187 (5)0.0254 (15)
C160.1906 (7)0.6258 (6)0.0480 (5)0.0216 (14)
C170.1642 (8)0.7477 (6)0.0344 (5)0.0272 (15)
H170.19120.76770.02000.033*
C180.0994 (8)0.8387 (6)0.0990 (5)0.0260 (15)
H180.08450.92140.08990.031*
C190.1443 (8)0.6006 (6)0.1281 (5)0.0223 (14)
C200.0767 (7)0.6954 (6)0.1893 (5)0.0201 (13)
H200.04350.67820.24220.024*
C210.9105 (9)0.3900 (6)0.7022 (6)0.0286 (16)
H21A0.85750.35190.77100.043*
H21B0.90710.47700.70160.043*
H21C1.01950.34970.68300.043*
C220.0137 (9)0.9120 (6)0.2434 (6)0.0282 (15)
H22A0.03160.87830.29700.042*
H22B0.05730.97200.27480.042*
H22C0.11340.95200.20340.042*
S2'0.7789 (2)0.85529 (17)0.20024 (15)0.0350 (5)
O1'0.2683 (6)0.8394 (5)0.1478 (4)0.0341 (12)
H1'0.259 (8)0.910 (7)0.107 (6)0.03 (2)*
N2'0.7545 (8)0.9531 (6)0.0007 (5)0.0369 (15)
C2'0.7644 (9)0.9120 (6)0.0824 (6)0.0301 (16)
C3'0.4216 (9)0.7800 (8)0.1352 (6)0.0403 (19)
H3'A0.44270.75370.20220.060*
H3'B0.49300.83600.09200.060*
H3'C0.43730.70840.10260.060*
S1'0.2143 (2)0.19609 (15)0.53003 (14)0.0284 (4)
N1'0.0725 (7)0.2967 (6)0.3713 (5)0.0300 (14)
C1'0.1311 (8)0.2521 (6)0.4362 (5)0.0243 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0369 (3)0.0195 (3)0.0274 (3)0.00819 (19)0.0173 (2)0.00561 (18)
I20.0294 (3)0.0206 (3)0.0248 (3)0.00555 (18)0.01539 (19)0.00677 (18)
N10.031 (3)0.022 (3)0.023 (3)0.007 (2)0.013 (2)0.009 (2)
N20.028 (3)0.023 (3)0.022 (3)0.004 (2)0.012 (2)0.008 (2)
C10.030 (4)0.022 (3)0.018 (3)0.008 (3)0.012 (3)0.001 (3)
C20.027 (3)0.023 (3)0.021 (3)0.009 (3)0.009 (3)0.006 (3)
C30.023 (3)0.027 (3)0.019 (3)0.009 (3)0.006 (3)0.009 (3)
C40.033 (4)0.019 (3)0.024 (3)0.004 (3)0.013 (3)0.006 (3)
C50.033 (4)0.019 (3)0.031 (4)0.004 (3)0.014 (3)0.009 (3)
C60.027 (3)0.022 (3)0.019 (3)0.006 (3)0.011 (3)0.005 (3)
C70.025 (3)0.024 (3)0.020 (3)0.007 (3)0.007 (3)0.002 (3)
C80.023 (3)0.025 (3)0.023 (3)0.007 (3)0.012 (3)0.006 (3)
C90.030 (4)0.028 (4)0.024 (4)0.006 (3)0.013 (3)0.005 (3)
C100.034 (4)0.028 (4)0.029 (4)0.013 (3)0.012 (3)0.007 (3)
C110.031 (4)0.035 (4)0.020 (3)0.009 (3)0.012 (3)0.012 (3)
C120.025 (3)0.025 (3)0.018 (3)0.007 (3)0.008 (3)0.008 (3)
C130.023 (3)0.036 (4)0.017 (3)0.005 (3)0.007 (3)0.006 (3)
C140.018 (3)0.023 (3)0.014 (3)0.006 (3)0.003 (2)0.011 (3)
C150.028 (4)0.032 (4)0.022 (3)0.006 (3)0.011 (3)0.009 (3)
C160.020 (3)0.032 (4)0.017 (3)0.009 (3)0.004 (3)0.008 (3)
C170.032 (4)0.032 (4)0.029 (4)0.010 (3)0.015 (3)0.012 (3)
C180.033 (4)0.027 (4)0.027 (4)0.008 (3)0.012 (3)0.015 (3)
C190.028 (3)0.022 (3)0.022 (3)0.007 (3)0.009 (3)0.007 (3)
C200.028 (3)0.026 (3)0.012 (3)0.006 (3)0.010 (3)0.006 (3)
C210.040 (4)0.029 (4)0.031 (4)0.009 (3)0.023 (3)0.011 (3)
C220.039 (4)0.024 (3)0.030 (4)0.005 (3)0.020 (3)0.006 (3)
S2'0.0541 (12)0.0253 (9)0.0383 (11)0.0063 (8)0.0287 (9)0.0082 (8)
O1'0.044 (3)0.033 (3)0.029 (3)0.007 (2)0.013 (2)0.005 (2)
N2'0.047 (4)0.035 (3)0.035 (4)0.012 (3)0.016 (3)0.007 (3)
C2'0.034 (4)0.025 (4)0.038 (5)0.004 (3)0.015 (3)0.011 (3)
C3'0.033 (4)0.056 (5)0.036 (4)0.014 (4)0.008 (3)0.012 (4)
S1'0.0404 (10)0.0230 (9)0.0315 (10)0.0059 (7)0.0196 (8)0.0095 (7)
N1'0.038 (3)0.034 (3)0.028 (3)0.014 (3)0.014 (3)0.011 (3)
C1'0.029 (4)0.024 (3)0.027 (4)0.011 (3)0.010 (3)0.011 (3)
Geometric parameters (Å, º) top
I1—C22.092 (6)C12—C131.393 (9)
I2—C192.101 (6)C13—C141.418 (9)
N1—C11.349 (8)C14—C151.210 (9)
N1—C51.336 (9)C15—C161.424 (9)
N1—C211.498 (8)C16—C171.398 (10)
N2—C181.349 (8)C16—C191.411 (9)
N2—C201.348 (9)C17—H170.9500
N2—C221.479 (9)C17—C181.371 (10)
C1—H10.9500C18—H180.9500
C1—C21.374 (9)C19—C201.378 (9)
C2—C31.408 (9)C20—H200.9500
C3—C41.405 (9)C21—H21A0.9800
C3—C61.420 (9)C21—H21B0.9800
C4—H40.9500C21—H21C0.9800
C4—C51.371 (9)C22—H22A0.9800
C5—H50.9500C22—H22B0.9800
C6—C71.198 (9)C22—H22C0.9800
C7—C81.432 (9)S2'—C2'1.662 (8)
C8—C91.400 (10)O1'—H1'0.88 (8)
C8—C121.398 (9)O1'—C3'1.389 (9)
C9—H90.9500N2'—C2'1.155 (10)
C9—C101.378 (10)C3'—H3'A0.9800
C10—H100.9500C3'—H3'B0.9800
C10—C111.392 (10)C3'—H3'C0.9800
C11—H110.9500S1'—C1'1.651 (7)
C11—C131.397 (10)N1'—C1'1.159 (9)
C12—H120.9500
C1—N1—C21118.3 (5)C12—C13—C14119.7 (6)
C5—N1—C1121.8 (6)C15—C14—C13179.4 (7)
C5—N1—C21119.9 (5)C14—C15—C16178.7 (7)
C18—N2—C22119.6 (6)C17—C16—C15120.5 (6)
C20—N2—C18120.6 (6)C17—C16—C19117.6 (6)
C20—N2—C22119.8 (5)C19—C16—C15121.9 (6)
N1—C1—H1119.9C16—C17—H17119.8
N1—C1—C2120.3 (6)C18—C17—C16120.4 (6)
C2—C1—H1119.9C18—C17—H17119.8
C1—C2—I1119.1 (5)N2—C18—C17120.8 (6)
C1—C2—C3119.7 (6)N2—C18—H18119.6
C3—C2—I1121.1 (5)C17—C18—H18119.6
C2—C3—C6120.5 (6)C16—C19—I2121.5 (5)
C4—C3—C2117.8 (6)C20—C19—I2119.0 (5)
C4—C3—C6121.7 (6)C20—C19—C16119.4 (6)
C3—C4—H4120.0N2—C20—C19121.2 (6)
C5—C4—C3119.9 (6)N2—C20—H20119.4
C5—C4—H4120.0C19—C20—H20119.4
N1—C5—C4120.5 (6)N1—C21—H21A109.5
N1—C5—H5119.7N1—C21—H21B109.5
C4—C5—H5119.7N1—C21—H21C109.5
C7—C6—C3176.7 (7)H21A—C21—H21B109.5
C6—C7—C8177.8 (7)H21A—C21—H21C109.5
C9—C8—C7120.3 (6)H21B—C21—H21C109.5
C12—C8—C7119.5 (6)N2—C22—H22A109.5
C12—C8—C9120.1 (6)N2—C22—H22B109.5
C8—C9—H9120.1N2—C22—H22C109.5
C10—C9—C8119.9 (6)H22A—C22—H22B109.5
C10—C9—H9120.1H22A—C22—H22C109.5
C9—C10—H10119.8H22B—C22—H22C109.5
C9—C10—C11120.3 (6)C3'—O1'—H1'114 (5)
C11—C10—H10119.8N2'—C2'—S2'178.9 (7)
C10—C11—H11119.9O1'—C3'—H3'A109.5
C10—C11—C13120.2 (6)O1'—C3'—H3'B109.5
C13—C11—H11119.9O1'—C3'—H3'C109.5
C8—C12—H12120.2H3'A—C3'—H3'B109.5
C13—C12—C8119.7 (6)H3'A—C3'—H3'C109.5
C13—C12—H12120.2H3'B—C3'—H3'C109.5
C11—C13—C14120.5 (6)N1'—C1'—S1'176.9 (6)
C12—C13—C11119.8 (6)
I1—C2—C3—C4175.5 (5)C9—C10—C11—C131.3 (11)
I1—C2—C3—C62.9 (9)C10—C11—C13—C120.5 (10)
I2—C19—C20—N2176.9 (5)C10—C11—C13—C14179.6 (6)
N1—C1—C2—I1175.1 (5)C12—C8—C9—C100.9 (10)
N1—C1—C2—C31.7 (10)C15—C16—C17—C18179.6 (6)
C1—N1—C5—C41.9 (10)C15—C16—C19—I22.8 (9)
C1—C2—C3—C41.2 (10)C15—C16—C19—C20178.9 (6)
C1—C2—C3—C6179.6 (6)C16—C17—C18—N21.5 (11)
C2—C3—C4—C51.0 (10)C16—C19—C20—N21.4 (10)
C3—C4—C5—N11.4 (10)C17—C16—C19—I2178.6 (5)
C5—N1—C1—C22.0 (10)C17—C16—C19—C200.3 (9)
C6—C3—C4—C5179.4 (6)C18—N2—C20—C191.7 (10)
C7—C8—C9—C10179.5 (6)C19—C16—C17—C181.7 (10)
C7—C8—C12—C13178.7 (6)C20—N2—C18—C170.2 (10)
C8—C9—C10—C110.6 (11)C21—N1—C1—C2176.3 (6)
C8—C12—C13—C111.0 (10)C21—N1—C5—C4176.4 (6)
C8—C12—C13—C14178.9 (6)C22—N2—C18—C17179.6 (7)
C9—C8—C12—C131.7 (10)C22—N2—C20—C19179.0 (6)
(arc_scn_ccl2) top
Crystal data top
C22H16I2N2·0.97(CH2Cl2)·2(CNS)Z = 2
Mr = 760.71F(000) = 733
Triclinic, P1Dx = 1.837 Mg m3
a = 7.7270 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.9671 (4) ÅCell parameters from 9372 reflections
c = 16.9780 (7) Åθ = 3.1–28.8°
α = 103.375 (2)°µ = 2.65 mm1
β = 98.725 (2)°T = 100 K
γ = 94.093 (2)°Rod, yellow
V = 1375.03 (9) Å30.5 × 0.05 × 0.02 mm
Data collection top
Bruker D8 VENTURE Duo
diffractometer
6282 independent reflections
Radiation source: sealed tube, fine-focus5184 reflections with I > 2σ(I)
TRIUMPH graphite monochromatorRint = 0.072
Detector resolution: 10.5 pixels mm-1θmax = 27.5°, θmin = 3.1°
φ and ω scansh = 1010
Absorption correction: multi-scan
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0802 before and 0.0670 after correction. The Ratio of minimum to maximum transmission is 0.7936. The λ/2 correction factor is 0.00150.
k = 1414
Tmin = 0.266, Tmax = 0.335l = 2222
105156 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0275P)2 + 2.1887P]
where P = (Fo2 + 2Fc2)/3
6282 reflections(Δ/σ)max = 0.002
328 parametersΔρmax = 1.01 e Å3
0 restraintsΔρmin = 0.65 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
I10.18696 (3)0.86748 (2)0.50650 (2)0.01936 (7)0.9689 (9)
I20.54771 (3)0.02447 (2)0.16788 (2)0.01870 (7)
Cl1'0.09272 (12)0.44158 (8)0.13780 (6)0.0277 (2)0.9689 (9)
Cl2'0.00038 (15)0.59527 (10)0.28783 (6)0.0392 (2)0.9689 (9)
N10.0012 (4)0.9647 (3)0.73683 (17)0.0212 (6)
N20.6731 (4)0.3021 (3)0.03692 (17)0.0206 (6)
C10.0522 (4)0.9661 (3)0.6649 (2)0.0198 (7)
H10.05701.04240.64750.024*
C20.0999 (4)0.8588 (3)0.61618 (19)0.0177 (7)
H20.13540.86050.56520.021*0.0311 (9)
C30.0951 (4)0.7465 (3)0.64334 (19)0.0175 (6)
C40.0365 (4)0.7488 (3)0.7180 (2)0.0208 (7)
H40.02940.67410.73720.025*0.9689 (9)
C50.0104 (4)0.8577 (3)0.7634 (2)0.0214 (7)
H50.04960.85820.81380.026*
C60.1500 (4)0.6348 (3)0.5982 (2)0.0188 (7)
C70.2008 (4)0.5417 (3)0.56097 (19)0.0180 (7)
C80.2620 (4)0.4311 (3)0.51513 (19)0.0170 (6)
C90.2802 (4)0.3254 (3)0.5475 (2)0.0224 (7)
H90.25430.32730.60070.027*
C100.3357 (4)0.2184 (3)0.5023 (2)0.0248 (7)
H100.34730.14670.52440.030*
C110.3747 (4)0.2152 (3)0.4248 (2)0.0218 (7)
H110.40940.14050.39330.026*
C120.3055 (4)0.4302 (3)0.4380 (2)0.0177 (6)
H120.29610.50250.41650.021*
C130.3630 (4)0.3217 (3)0.3930 (2)0.0201 (7)
C140.4124 (4)0.3185 (3)0.3145 (2)0.0217 (7)
C150.4606 (4)0.3113 (3)0.2505 (2)0.0217 (7)
C160.5301 (4)0.3067 (3)0.1768 (2)0.0188 (7)
C170.5584 (4)0.4162 (3)0.1501 (2)0.0234 (7)
H170.52880.49380.18030.028*
C180.6290 (4)0.4120 (3)0.0802 (2)0.0248 (8)
H180.64700.48680.06200.030*
C190.5763 (4)0.1935 (3)0.13068 (19)0.0166 (6)
C200.6489 (4)0.1940 (3)0.0611 (2)0.0188 (7)
H200.68190.11800.03020.023*
C210.0358 (5)1.0845 (4)0.7904 (2)0.0315 (9)
H21A0.07121.14430.80500.047*
H21B0.07071.06830.84050.047*
H21C0.13091.12020.76100.047*
C220.7459 (5)0.3008 (4)0.0387 (2)0.0309 (9)
H22A0.65060.27610.08640.046*
H22B0.83330.24030.04430.046*
H22C0.80210.38520.03560.046*
S1'0.55424 (13)0.78079 (8)0.25082 (6)0.0283 (2)
N1'0.3380 (4)0.8873 (3)0.3623 (2)0.0345 (8)
C1'0.4290 (5)0.8434 (3)0.3176 (2)0.0240 (7)
S2'0.13575 (13)0.12884 (9)0.01607 (6)0.0308 (2)
N2'0.2668 (5)0.3146 (3)0.0526 (2)0.0363 (8)
C2'0.2181 (5)0.2425 (4)0.0240 (2)0.0294 (8)
I1A0.0025 (13)0.5791 (11)0.7600 (6)0.053 (3)0.0311 (9)
C0AA0.0672 (5)0.5952 (3)0.1930 (2)0.0301 (9)0.9689 (9)
H0AA0.18040.64940.20310.036*0.9689 (9)
H0AB0.02170.63150.15940.036*0.9689 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.01733 (12)0.02435 (13)0.01905 (12)0.00475 (9)0.00552 (9)0.00840 (9)
I20.01878 (12)0.01783 (11)0.01987 (12)0.00113 (8)0.00306 (8)0.00654 (8)
Cl1'0.0312 (5)0.0265 (4)0.0258 (5)0.0043 (4)0.0081 (4)0.0048 (4)
Cl2'0.0556 (7)0.0321 (5)0.0342 (6)0.0056 (5)0.0236 (5)0.0062 (4)
N10.0159 (14)0.0264 (15)0.0184 (14)0.0042 (11)0.0023 (11)0.0003 (12)
N20.0178 (14)0.0271 (15)0.0166 (14)0.0037 (11)0.0026 (11)0.0072 (12)
C10.0165 (16)0.0224 (17)0.0194 (17)0.0017 (13)0.0009 (13)0.0049 (13)
C20.0121 (15)0.0230 (17)0.0163 (16)0.0017 (12)0.0001 (12)0.0033 (13)
C30.0112 (15)0.0208 (16)0.0180 (16)0.0011 (12)0.0001 (12)0.0019 (13)
C40.0171 (16)0.0228 (17)0.0208 (17)0.0035 (13)0.0009 (13)0.0053 (14)
C50.0173 (16)0.0298 (18)0.0155 (16)0.0001 (14)0.0028 (13)0.0029 (14)
C60.0144 (16)0.0242 (17)0.0172 (16)0.0023 (13)0.0009 (13)0.0065 (14)
C70.0130 (15)0.0238 (17)0.0161 (16)0.0027 (13)0.0017 (13)0.0051 (13)
C80.0108 (15)0.0210 (16)0.0173 (16)0.0006 (12)0.0017 (12)0.0015 (13)
C90.0179 (17)0.0299 (19)0.0198 (17)0.0007 (14)0.0017 (13)0.0089 (14)
C100.0201 (17)0.0219 (17)0.033 (2)0.0032 (13)0.0008 (15)0.0104 (15)
C110.0158 (16)0.0197 (17)0.0269 (18)0.0039 (13)0.0002 (14)0.0015 (14)
C120.0115 (15)0.0199 (16)0.0193 (17)0.0000 (12)0.0011 (12)0.0033 (13)
C130.0108 (15)0.0266 (18)0.0202 (17)0.0010 (13)0.0003 (13)0.0033 (14)
C140.0125 (15)0.0240 (17)0.0241 (18)0.0003 (13)0.0006 (13)0.0004 (14)
C150.0143 (16)0.0246 (18)0.0231 (18)0.0026 (13)0.0018 (14)0.0002 (14)
C160.0131 (15)0.0230 (17)0.0175 (16)0.0014 (12)0.0010 (13)0.0028 (13)
C170.0196 (17)0.0184 (17)0.0292 (19)0.0007 (13)0.0013 (14)0.0028 (14)
C180.0214 (18)0.0205 (17)0.032 (2)0.0037 (14)0.0034 (15)0.0120 (15)
C190.0144 (15)0.0177 (16)0.0168 (16)0.0014 (12)0.0007 (12)0.0053 (13)
C200.0178 (16)0.0169 (16)0.0201 (17)0.0018 (12)0.0009 (13)0.0039 (13)
C210.031 (2)0.033 (2)0.026 (2)0.0095 (16)0.0037 (16)0.0013 (16)
C220.035 (2)0.039 (2)0.0227 (19)0.0032 (17)0.0076 (16)0.0162 (17)
S1'0.0350 (5)0.0244 (5)0.0279 (5)0.0036 (4)0.0072 (4)0.0100 (4)
N1'0.0375 (19)0.0386 (19)0.0310 (18)0.0045 (15)0.0074 (16)0.0151 (15)
C1'0.0253 (18)0.0240 (18)0.0231 (18)0.0026 (14)0.0019 (15)0.0120 (15)
S2'0.0337 (5)0.0298 (5)0.0301 (5)0.0009 (4)0.0052 (4)0.0110 (4)
N2'0.041 (2)0.0266 (18)0.037 (2)0.0016 (15)0.0014 (16)0.0045 (15)
C2'0.027 (2)0.030 (2)0.0232 (19)0.0049 (16)0.0052 (16)0.0044 (16)
I1A0.035 (5)0.073 (8)0.048 (6)0.013 (5)0.002 (4)0.016 (5)
C0AA0.039 (2)0.024 (2)0.028 (2)0.0001 (16)0.0109 (17)0.0053 (16)
Geometric parameters (Å, º) top
I1—C22.093 (3)C10—C111.387 (5)
I2—C192.100 (3)C11—H110.9500
Cl1'—C0AA1.769 (4)C11—C131.399 (5)
Cl2'—C0AA1.764 (4)C12—H120.9500
N1—C11.349 (4)C12—C131.398 (5)
N1—C51.352 (4)C13—C141.434 (5)
N1—C211.482 (4)C14—C151.189 (5)
N2—C181.354 (5)C15—C161.427 (5)
N2—C201.351 (4)C16—C171.392 (5)
N2—C221.475 (4)C16—C191.407 (5)
C1—H10.9500C17—H170.9500
C1—C21.383 (5)C17—C181.373 (5)
C2—H20.9500C18—H180.9500
C2—C31.411 (5)C19—C201.383 (4)
C3—C41.405 (5)C20—H200.9500
C3—C61.416 (5)C21—H21A0.9800
C4—H40.9500C21—H21B0.9800
C4—C51.368 (5)C21—H21C0.9800
C4—I1A2.154 (12)C22—H22A0.9800
C5—H50.9500C22—H22B0.9800
C6—C71.196 (5)C22—H22C0.9800
C7—C81.435 (5)S1'—C1'1.662 (4)
C8—C91.400 (5)N1'—C1'1.158 (5)
C8—C121.398 (4)S2'—C2'1.682 (4)
C9—H90.9500N2'—C2'1.093 (5)
C9—C101.380 (5)C0AA—H0AA0.9900
C10—H100.9500C0AA—H0AB0.9900
C1—N1—C5120.9 (3)C13—C12—H12120.4
C1—N1—C21119.3 (3)C11—C13—C14119.3 (3)
C5—N1—C21119.6 (3)C12—C13—C11120.0 (3)
C18—N2—C22119.0 (3)C12—C13—C14120.7 (3)
C20—N2—C18121.2 (3)C15—C14—C13176.1 (4)
C20—N2—C22119.8 (3)C14—C15—C16176.0 (4)
N1—C1—H1119.3C17—C16—C15120.2 (3)
N1—C1—C2121.3 (3)C17—C16—C19118.4 (3)
C2—C1—H1119.3C19—C16—C15121.4 (3)
C1—C2—I1119.6 (2)C16—C17—H17120.0
C1—C2—H2120.5C18—C17—C16120.1 (3)
C1—C2—C3118.9 (3)C18—C17—H17120.0
C3—C2—I1121.4 (2)N2—C18—C17120.5 (3)
C3—C2—H2120.5N2—C18—H18119.7
C2—C3—C6121.7 (3)C17—C18—H18119.7
C4—C3—C2117.9 (3)C16—C19—I2121.4 (2)
C4—C3—C6120.4 (3)C20—C19—I2119.0 (2)
C3—C4—H4119.7C20—C19—C16119.6 (3)
C3—C4—I1A120.9 (4)N2—C20—C19120.3 (3)
C5—C4—C3120.6 (3)N2—C20—H20119.9
C5—C4—H4119.7C19—C20—H20119.9
C5—C4—I1A118.4 (4)N1—C21—H21A109.5
N1—C5—C4120.4 (3)N1—C21—H21B109.5
N1—C5—H5119.8N1—C21—H21C109.5
C4—C5—H5119.8H21A—C21—H21B109.5
C7—C6—C3178.3 (4)H21A—C21—H21C109.5
C6—C7—C8179.0 (3)H21B—C21—H21C109.5
C9—C8—C7120.5 (3)N2—C22—H22A109.5
C12—C8—C7119.4 (3)N2—C22—H22B109.5
C12—C8—C9120.1 (3)N2—C22—H22C109.5
C8—C9—H9119.9H22A—C22—H22B109.5
C10—C9—C8120.2 (3)H22A—C22—H22C109.5
C10—C9—H9119.9H22B—C22—H22C109.5
C9—C10—H10119.9N1'—C1'—S1'178.0 (3)
C9—C10—C11120.2 (3)N2'—C2'—S2'177.3 (4)
C11—C10—H10119.9Cl1'—C0AA—H0AA109.2
C10—C11—H11119.9Cl1'—C0AA—H0AB109.2
C10—C11—C13120.2 (3)Cl2'—C0AA—Cl1'112.0 (2)
C13—C11—H11119.9Cl2'—C0AA—H0AA109.2
C8—C12—H12120.4Cl2'—C0AA—H0AB109.2
C8—C12—C13119.3 (3)H0AA—C0AA—H0AB107.9
I1—C2—C3—C4179.4 (2)C9—C10—C11—C131.9 (5)
I1—C2—C3—C60.5 (4)C10—C11—C13—C122.4 (5)
I2—C19—C20—N2178.3 (2)C10—C11—C13—C14176.9 (3)
N1—C1—C2—I1178.7 (2)C12—C8—C9—C102.1 (5)
N1—C1—C2—C31.0 (5)C15—C16—C17—C18178.6 (3)
C1—N1—C5—C40.8 (5)C15—C16—C19—I20.5 (4)
C1—C2—C3—C41.8 (4)C15—C16—C19—C20177.8 (3)
C1—C2—C3—C6177.1 (3)C16—C17—C18—N20.6 (5)
C2—C3—C4—C51.4 (5)C16—C19—C20—N20.9 (5)
C2—C3—C4—I1A174.7 (4)C17—C16—C19—I2177.8 (2)
C3—C4—C5—N10.1 (5)C17—C16—C19—C200.5 (5)
C5—N1—C1—C20.3 (5)C18—N2—C20—C190.7 (5)
C6—C3—C4—C5177.5 (3)C19—C16—C17—C180.3 (5)
C6—C3—C4—I1A6.4 (5)C20—N2—C18—C170.1 (5)
C7—C8—C9—C10178.7 (3)C21—N1—C1—C2174.6 (3)
C7—C8—C12—C13179.2 (3)C21—N1—C5—C4174.1 (3)
C8—C9—C10—C110.3 (5)C22—N2—C18—C17179.0 (3)
C8—C12—C13—C110.7 (5)C22—N2—C20—C19178.2 (3)
C8—C12—C13—C14178.6 (3)I1A—C4—C5—N1176.0 (4)
C9—C8—C12—C131.6 (5)
(arc_3i) top
Crystal data top
C22H16I2N2·2(I3)F(000) = 2344
Mr = 1323.57Dx = 2.725 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
a = 7.3983 (4) ÅCell parameters from 9877 reflections
b = 10.4370 (5) Åθ = 4.2–58.9°
c = 41.8567 (18) ŵ = 60.50 mm1
β = 93.424 (2)°T = 100 K
V = 3226.2 (3) Å3Plate, yellow
Z = 40.5 × 0.05 × 0.05 mm
Data collection top
Bruker D8 VENTURE Duo
diffractometer
4551 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµus3685 reflections with I > 2σ(I)
Double Bounce Multilayer Mirror monochromatorRint = 0.066
Detector resolution: 10.5 pixels mm-1θmax = 59.0°, θmin = 2.1°
ω and φ scansh = 77
Absorption correction: multi-scan
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1487 before and 0.0779 after correction. The Ratio of minimum to maximum transmission is 0.1037. The λ/2 correction factor is 0.00150.
k = 1111
Tmin = 0.010, Tmax = 0.097l = 4545
26322 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.109 w = 1/[σ2(Fo2) + (0.0517P)2 + 12.8486P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
4551 reflectionsΔρmax = 1.05 e Å3
291 parametersΔρmin = 0.64 e Å3
198 restraints
Special details top

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 (Å2) top
xyzUiso*/Ueq
I10.61011 (11)0.23036 (7)0.33918 (2)0.0561 (2)
I20.08369 (11)0.38641 (7)0.60206 (2)0.0561 (2)
N10.5933 (14)0.5954 (9)0.2929 (2)0.055 (2)
N20.0466 (13)0.7840 (8)0.6094 (2)0.052 (2)
C10.6184 (15)0.4707 (10)0.3005 (3)0.047 (2)
H10.67200.41490.28580.056*
C20.5679 (16)0.4246 (10)0.3288 (3)0.048 (2)
C30.4955 (15)0.5063 (11)0.3510 (3)0.051 (2)
C40.4729 (17)0.6350 (11)0.3421 (3)0.057 (3)
H40.42290.69360.35650.069*
C50.5212 (17)0.6773 (12)0.3132 (3)0.057 (3)
H50.50410.76470.30750.068*
C60.4529 (16)0.4648 (11)0.3821 (3)0.054 (3)
C70.4254 (17)0.4304 (10)0.4089 (3)0.052 (3)
C80.3913 (15)0.3849 (10)0.4398 (3)0.049 (2)
C90.4310 (14)0.2554 (10)0.4476 (3)0.048 (2)
H90.48010.20090.43210.057*
C100.3986 (17)0.2078 (12)0.4776 (3)0.059 (3)
H100.42480.12090.48290.071*
C110.3275 (16)0.2886 (10)0.5000 (3)0.054 (3)
H110.30570.25630.52060.065*
C120.3202 (15)0.4629 (11)0.4633 (3)0.050 (3)
H120.29400.55040.45870.060*
C130.2883 (15)0.4131 (10)0.4930 (3)0.049 (2)
C140.2213 (16)0.4950 (11)0.5171 (3)0.052 (3)
C150.1658 (16)0.5584 (11)0.5382 (3)0.050 (3)
C160.0939 (16)0.6344 (10)0.5628 (3)0.048 (2)
C170.0684 (16)0.7667 (11)0.5588 (3)0.054 (3)
H170.10000.80650.53950.065*
C180.0016 (16)0.8388 (11)0.5823 (3)0.051 (3)
H180.01820.92840.57940.061*
C190.0480 (15)0.5817 (10)0.5921 (2)0.046 (2)
C200.0243 (15)0.6585 (10)0.6150 (2)0.044 (2)
H200.05790.62250.63460.053*
C210.6520 (19)0.6441 (12)0.2618 (3)0.063 (3)
H21A0.78240.63030.26060.095*
H21B0.62540.73590.26000.095*
H21C0.58670.59820.24420.095*
C220.1224 (18)0.8630 (11)0.6349 (3)0.057 (3)
H22A0.15260.80760.65280.085*
H22B0.23200.90670.62630.085*
H22C0.03260.92680.64260.085*
I4'0.68742 (11)0.92454 (7)0.37915 (2)0.0575 (2)
I5'0.40182 (11)0.88566 (7)0.42534 (2)0.0523 (2)
I6'0.12261 (12)0.86443 (7)0.46972 (2)0.0600 (2)
I1'0.41788 (11)0.92114 (9)0.20433 (2)0.0640 (2)
I2'0.20266 (11)0.87194 (8)0.26097 (2)0.0574 (2)
I3'0.00851 (13)0.83877 (9)0.31502 (2)0.0714 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0568 (5)0.0469 (4)0.0644 (5)0.0012 (3)0.0025 (4)0.0031 (3)
I20.0685 (6)0.0438 (4)0.0551 (5)0.0044 (4)0.0032 (4)0.0016 (3)
N10.067 (6)0.053 (4)0.046 (4)0.000 (4)0.003 (4)0.009 (3)
N20.063 (6)0.044 (4)0.049 (4)0.005 (4)0.001 (4)0.002 (3)
C10.042 (6)0.048 (4)0.049 (5)0.005 (4)0.003 (4)0.000 (4)
C20.054 (7)0.047 (5)0.043 (4)0.006 (4)0.006 (4)0.002 (3)
C30.049 (6)0.049 (4)0.053 (5)0.007 (4)0.002 (4)0.002 (3)
C40.067 (8)0.050 (5)0.054 (5)0.005 (5)0.003 (5)0.002 (4)
C50.063 (7)0.054 (5)0.053 (5)0.001 (5)0.003 (5)0.004 (4)
C60.052 (7)0.057 (6)0.052 (4)0.011 (5)0.005 (4)0.006 (4)
C70.061 (8)0.042 (5)0.054 (4)0.010 (5)0.000 (4)0.010 (4)
C80.046 (6)0.048 (5)0.052 (4)0.003 (4)0.001 (4)0.005 (3)
C90.034 (6)0.050 (5)0.058 (5)0.002 (4)0.007 (4)0.007 (4)
C100.060 (8)0.054 (5)0.063 (5)0.003 (5)0.003 (5)0.003 (4)
C110.064 (7)0.042 (4)0.055 (5)0.005 (4)0.004 (5)0.001 (4)
C120.050 (7)0.047 (5)0.052 (4)0.002 (4)0.000 (4)0.001 (4)
C130.048 (6)0.046 (4)0.053 (5)0.005 (4)0.001 (4)0.003 (3)
C140.059 (7)0.046 (5)0.051 (5)0.004 (5)0.002 (5)0.002 (4)
C150.048 (6)0.057 (6)0.043 (5)0.000 (5)0.012 (4)0.001 (4)
C160.052 (7)0.050 (4)0.042 (4)0.003 (4)0.005 (4)0.001 (3)
C170.063 (7)0.053 (5)0.046 (5)0.001 (4)0.001 (5)0.006 (4)
C180.058 (7)0.044 (5)0.049 (5)0.004 (4)0.004 (4)0.006 (4)
C190.051 (6)0.043 (4)0.042 (4)0.005 (4)0.004 (4)0.001 (3)
C200.051 (6)0.044 (4)0.038 (5)0.006 (4)0.004 (4)0.004 (3)
C210.074 (8)0.068 (7)0.047 (5)0.005 (6)0.005 (5)0.011 (5)
C220.076 (8)0.046 (6)0.049 (6)0.003 (5)0.008 (5)0.004 (4)
I4'0.0682 (5)0.0429 (4)0.0623 (5)0.0027 (4)0.0120 (4)0.0002 (3)
I5'0.0645 (5)0.0427 (4)0.0497 (4)0.0014 (3)0.0039 (4)0.0007 (3)
I6'0.0703 (6)0.0588 (5)0.0514 (4)0.0023 (4)0.0080 (4)0.0047 (3)
I1'0.0587 (5)0.0844 (6)0.0490 (5)0.0013 (4)0.0031 (4)0.0040 (4)
I2'0.0595 (5)0.0635 (5)0.0490 (4)0.0045 (4)0.0018 (4)0.0008 (3)
I3'0.0856 (7)0.0716 (6)0.0586 (5)0.0142 (5)0.0183 (4)0.0098 (4)
Geometric parameters (Å, º) top
I1—C22.093 (11)C11—H110.9500
I2—C192.094 (11)C11—C131.360 (15)
N1—C11.350 (14)C12—H120.9500
N1—C51.340 (15)C12—C131.382 (15)
N1—C211.486 (14)C13—C141.433 (16)
N2—C181.328 (14)C14—C151.197 (15)
N2—C201.339 (14)C15—C161.429 (16)
N2—C221.487 (14)C16—C171.402 (15)
C1—H10.9500C16—C191.402 (15)
C1—C21.352 (15)C17—H170.9500
C2—C31.393 (15)C17—C181.367 (16)
C3—C41.402 (16)C18—H180.9500
C3—C61.425 (16)C19—C201.383 (15)
C4—H40.9500C20—H200.9500
C4—C51.353 (16)C21—H21A0.9800
C5—H50.9500C21—H21B0.9800
C6—C71.204 (15)C21—H21C0.9800
C7—C81.416 (16)C22—H22A0.9800
C8—C91.417 (15)C22—H22B0.9800
C8—C121.402 (15)C22—H22C0.9800
C9—H90.9500I4'—I5'2.9755 (10)
C9—C101.388 (16)I5'—I6'2.8681 (11)
C10—H100.9500I1'—I2'2.9781 (11)
C10—C111.386 (16)I2'—I3'2.8464 (11)
C1—N1—C21119.5 (10)C13—C12—C8120.2 (11)
C5—N1—C1121.3 (10)C13—C12—H12119.9
C5—N1—C21119.2 (10)C11—C13—C12120.5 (11)
C18—N2—C20122.5 (10)C11—C13—C14119.8 (11)
C18—N2—C22119.9 (9)C12—C13—C14119.6 (10)
C20—N2—C22117.6 (9)C15—C14—C13176.8 (12)
N1—C1—H1119.7C14—C15—C16178.1 (13)
N1—C1—C2120.6 (11)C17—C16—C15120.9 (10)
C2—C1—H1119.7C19—C16—C15122.1 (10)
C1—C2—I1118.8 (8)C19—C16—C17117.0 (10)
C1—C2—C3120.3 (10)C16—C17—H17119.7
C3—C2—I1120.8 (8)C18—C17—C16120.6 (11)
C2—C3—C4117.0 (11)C18—C17—H17119.7
C2—C3—C6122.7 (10)N2—C18—C17120.2 (10)
C4—C3—C6120.3 (11)N2—C18—H18119.9
C3—C4—H4119.4C17—C18—H18119.9
C5—C4—C3121.1 (12)C16—C19—I2121.5 (8)
C5—C4—H4119.4C20—C19—I2118.3 (8)
N1—C5—C4119.7 (11)C20—C19—C16120.2 (10)
N1—C5—H5120.1N2—C20—C19119.5 (10)
C4—C5—H5120.1N2—C20—H20120.2
C7—C6—C3176.9 (13)C19—C20—H20120.2
C6—C7—C8177.7 (12)N1—C21—H21A109.5
C7—C8—C9118.9 (10)N1—C21—H21B109.5
C12—C8—C7122.8 (10)N1—C21—H21C109.5
C12—C8—C9118.3 (10)H21A—C21—H21B109.5
C8—C9—H9119.8H21A—C21—H21C109.5
C10—C9—C8120.3 (11)H21B—C21—H21C109.5
C10—C9—H9119.8N2—C22—H22A109.5
C9—C10—H10120.4N2—C22—H22B109.5
C11—C10—C9119.2 (11)N2—C22—H22C109.5
C11—C10—H10120.4H22A—C22—H22B109.5
C10—C11—H11119.3H22A—C22—H22C109.5
C13—C11—C10121.4 (11)H22B—C22—H22C109.5
C13—C11—H11119.3I6'—I5'—I4'176.56 (3)
C8—C12—H12119.9I3'—I2'—I1'176.98 (4)
I1—C2—C3—C4179.6 (9)C9—C10—C11—C130.3 (18)
I1—C2—C3—C62.5 (16)C10—C11—C13—C120.6 (19)
I2—C19—C20—N2179.2 (8)C10—C11—C13—C14177.7 (11)
N1—C1—C2—I1179.9 (8)C12—C8—C9—C100.5 (17)
N1—C1—C2—C32.4 (17)C15—C16—C17—C18179.5 (11)
C1—N1—C5—C40.3 (18)C15—C16—C19—I20.5 (16)
C1—C2—C3—C42.1 (17)C15—C16—C19—C20178.8 (11)
C1—C2—C3—C6175.1 (11)C16—C17—C18—N20.1 (18)
C2—C3—C4—C50.6 (18)C16—C19—C20—N21.4 (17)
C3—C4—C5—N10.6 (19)C17—C16—C19—I2178.7 (8)
C5—N1—C1—C21.2 (17)C17—C16—C19—C201.9 (17)
C6—C3—C4—C5176.6 (12)C18—N2—C20—C190.0 (17)
C7—C8—C9—C10179.8 (11)C19—C16—C17—C181.2 (18)
C7—C8—C12—C13179.5 (11)C20—N2—C18—C170.8 (18)
C8—C9—C10—C110.2 (17)C21—N1—C1—C2179.3 (11)
C8—C12—C13—C110.9 (18)C21—N1—C5—C4177.8 (12)
C8—C12—C13—C14178.0 (11)C22—N2—C18—C17179.9 (11)
C9—C8—C12—C130.8 (17)C22—N2—C20—C19179.2 (10)
 

Follow Acta Cryst. B
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds