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
CCDC references: 1520140; 1520141; 1520142; 1520143
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).
Crystal data top
C22H16I2N2·C3H7NO·2(CF3O3S) | Dx = 1.877 Mg m−3 |
Mr = 933.40 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbcn | Cell parameters from 9865 reflections |
a = 22.4519 (12) Å | θ = 3.3–30.5° |
b = 18.1915 (9) Å | µ = 2.11 mm−1 |
c = 8.0879 (4) Å | T = 100 K |
V = 3303.4 (3) Å3 | Rod, yellow |
Z = 4 | 0.5 × 0.05 × 0.03 mm |
F(000) = 1816 | |
Data collection top
Bruker D8 VENTURE Duo diffractometer | 3786 independent reflections |
Radiation source: sealed tube, fine-focus | 3280 reflections with I > 2σ(I) |
TRIUMPH graphite monochromator | Rint = 0.075 |
Detector resolution: 10.5 pixels mm-1 | θmax = 27.5°, θmin = 2.9° |
ω and φ scans | h = −29→29 |
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 = −23→23 |
Tmin = 0.193, Tmax = 0.266 | l = −10→10 |
83218 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-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 parameters | Δρmax = 0.92 e Å−3 |
0 restraints | Δρmin = −1.29 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
I1 | 0.40238 (2) | 0.34468 (2) | 0.61791 (5) | 0.02618 (13) | |
N1 | 0.2514 (2) | 0.3718 (3) | 0.3026 (6) | 0.0221 (11) | |
C1 | 0.2955 (3) | 0.3450 (4) | 0.3973 (7) | 0.0243 (12) | |
H1 | 0.2989 | 0.2934 | 0.4126 | 0.029* | |
C2 | 0.3358 (2) | 0.3908 (3) | 0.4723 (7) | 0.0193 (12) | |
C3 | 0.3311 (3) | 0.4677 (3) | 0.4468 (7) | 0.0209 (12) | |
C4 | 0.2844 (3) | 0.4925 (4) | 0.3475 (7) | 0.0234 (13) | |
H4 | 0.2798 | 0.5437 | 0.3286 | 0.028* | |
C5 | 0.2450 (3) | 0.4445 (4) | 0.2769 (8) | 0.0244 (13) | |
H5 | 0.2133 | 0.4624 | 0.2102 | 0.029* | |
C6 | 0.3729 (3) | 0.5163 (3) | 0.5191 (8) | 0.0209 (13) | |
C7 | 0.4099 (3) | 0.5543 (3) | 0.5826 (8) | 0.0245 (13) | |
C8 | 0.4550 (3) | 0.5952 (3) | 0.6666 (8) | 0.0221 (13) | |
C9 | 0.4556 (3) | 0.6723 (3) | 0.6679 (9) | 0.0293 (15) | |
H9 | 0.4252 | 0.6987 | 0.6119 | 0.035* | |
C10 | 0.5000 | 0.7102 (5) | 0.7500 | 0.034 (2) | |
H10 | 0.5000 | 0.7624 | 0.7500 | 0.041* | |
C11 | 0.5000 | 0.5567 (5) | 0.7500 | 0.0217 (18) | |
H11 | 0.5000 | 0.5045 | 0.7500 | 0.026* | |
C12 | 0.2076 (3) | 0.3197 (4) | 0.2310 (9) | 0.0308 (15) | |
H12A | 0.2243 | 0.2699 | 0.2325 | 0.046* | |
H12B | 0.1988 | 0.3340 | 0.1168 | 0.046* | |
H12C | 0.1709 | 0.3209 | 0.2965 | 0.046* | |
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' | 0.4405 | 0.2026 | 0.9008 | 0.035* | 0.5 |
C2' | 0.4606 (8) | 0.0689 (9) | 0.828 (2) | 0.044 (4) | 0.5 |
H2'A | 0.4356 | 0.0802 | 0.9242 | 0.066* | 0.5 |
H2'B | 0.4913 | 0.0333 | 0.8598 | 0.066* | 0.5 |
H2'C | 0.4358 | 0.0480 | 0.7401 | 0.066* | 0.5 |
C3' | 0.5378 (9) | 0.1289 (11) | 0.654 (3) | 0.050 (5) | 0.5 |
H3'A | 0.5495 | 0.1778 | 0.6150 | 0.075* | 0.5 |
H3'B | 0.5256 | 0.0986 | 0.5599 | 0.075* | 0.5 |
H3'C | 0.5717 | 0.1057 | 0.7100 | 0.075* | 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 | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.0252 (2) | 0.0252 (2) | 0.0282 (2) | −0.00057 (18) | −0.01022 (17) | 0.00706 (19) |
N1 | 0.019 (2) | 0.031 (3) | 0.017 (2) | 0.005 (2) | 0.001 (2) | −0.002 (2) |
C1 | 0.028 (3) | 0.027 (3) | 0.018 (3) | 0.005 (3) | 0.000 (2) | 0.003 (3) |
C2 | 0.015 (3) | 0.027 (3) | 0.016 (3) | 0.004 (2) | 0.002 (2) | 0.002 (2) |
C3 | 0.019 (3) | 0.025 (3) | 0.019 (3) | 0.003 (2) | 0.005 (2) | 0.004 (2) |
C4 | 0.023 (3) | 0.026 (3) | 0.021 (3) | 0.009 (3) | 0.006 (3) | 0.004 (3) |
C5 | 0.019 (3) | 0.034 (3) | 0.020 (3) | 0.010 (3) | 0.002 (3) | 0.007 (3) |
C6 | 0.015 (3) | 0.024 (3) | 0.024 (3) | 0.003 (2) | 0.007 (2) | 0.006 (3) |
C7 | 0.017 (3) | 0.026 (3) | 0.030 (3) | 0.005 (2) | 0.008 (3) | 0.006 (3) |
C8 | 0.015 (3) | 0.019 (3) | 0.032 (3) | 0.002 (2) | 0.010 (2) | 0.002 (3) |
C9 | 0.025 (3) | 0.015 (3) | 0.048 (4) | 0.006 (2) | 0.009 (3) | 0.007 (3) |
C10 | 0.029 (5) | 0.009 (4) | 0.064 (7) | 0.000 | 0.020 (5) | 0.000 |
C11 | 0.020 (4) | 0.019 (4) | 0.027 (5) | 0.000 | 0.008 (4) | 0.000 |
C12 | 0.026 (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—C2 | 2.080 (6) | C12—H12A | 0.9800 |
N1—C1 | 1.344 (8) | C12—H12B | 0.9800 |
N1—C5 | 1.347 (8) | C12—H12C | 0.9800 |
N1—C12 | 1.482 (8) | O1'—C1' | 1.215 (17) |
C1—H1 | 0.9500 | N1'—C1' | 1.321 (17) |
C1—C2 | 1.371 (9) | N1'—C2' | 1.452 (18) |
C2—C3 | 1.418 (8) | N1'—C3' | 1.45 (2) |
C3—C4 | 1.395 (8) | C1'—H1' | 0.9500 |
C3—C6 | 1.417 (9) | C2'—H2'A | 0.9800 |
C4—H4 | 0.9500 | C2'—H2'B | 0.9800 |
C4—C5 | 1.367 (9) | C2'—H2'C | 0.9800 |
C5—H5 | 0.9500 | C3'—H3'A | 0.9800 |
C6—C7 | 1.196 (9) | C3'—H3'B | 0.9800 |
C7—C8 | 1.429 (9) | C3'—H3'C | 0.9800 |
C8—C9 | 1.403 (8) | S1'—O2' | 1.452 (5) |
C8—C11 | 1.402 (7) | S1'—O3' | 1.427 (5) |
C9—H9 | 0.9500 | S1'—O4' | 1.430 (5) |
C9—C10 | 1.382 (8) | S1'—C4' | 1.814 (7) |
C10—C9i | 1.382 (8) | F1'—C4' | 1.337 (9) |
C10—H10 | 0.9500 | F2'—C4' | 1.321 (8) |
C11—C8i | 1.402 (7) | F3'—C4' | 1.327 (9) |
C11—H11 | 0.9500 | | |
| | | |
C1—N1—C5 | 121.5 (6) | N1—C12—H12C | 109.5 |
C1—N1—C12 | 118.7 (5) | H12A—C12—H12B | 109.5 |
C5—N1—C12 | 119.8 (5) | H12A—C12—H12C | 109.5 |
N1—C1—H1 | 119.4 | H12B—C12—H12C | 109.5 |
N1—C1—C2 | 121.2 (6) | C1'—N1'—C2' | 121.6 (13) |
C2—C1—H1 | 119.4 | C1'—N1'—C3' | 120.3 (14) |
C1—C2—I1 | 118.6 (4) | C3'—N1'—C2' | 118.1 (14) |
C1—C2—C3 | 119.1 (5) | O1'—C1'—N1' | 126.0 (15) |
C3—C2—I1 | 122.3 (4) | O1'—C1'—H1' | 117.0 |
C4—C3—C2 | 117.3 (6) | N1'—C1'—H1' | 117.0 |
C4—C3—C6 | 122.3 (6) | N1'—C2'—H2'A | 109.5 |
C6—C3—C2 | 120.4 (5) | N1'—C2'—H2'B | 109.5 |
C3—C4—H4 | 119.3 | N1'—C2'—H2'C | 109.5 |
C5—C4—C3 | 121.3 (6) | H2'A—C2'—H2'B | 109.5 |
C5—C4—H4 | 119.3 | H2'A—C2'—H2'C | 109.5 |
N1—C5—C4 | 119.6 (6) | H2'B—C2'—H2'C | 109.5 |
N1—C5—H5 | 120.2 | N1'—C3'—H3'A | 109.5 |
C4—C5—H5 | 120.2 | N1'—C3'—H3'B | 109.5 |
C7—C6—C3 | 176.6 (6) | N1'—C3'—H3'C | 109.5 |
C6—C7—C8 | 175.8 (7) | H3'A—C3'—H3'B | 109.5 |
C9—C8—C7 | 122.1 (6) | H3'A—C3'—H3'C | 109.5 |
C11—C8—C7 | 118.6 (6) | H3'B—C3'—H3'C | 109.5 |
C11—C8—C9 | 119.3 (6) | O2'—S1'—C4' | 102.9 (3) |
C8—C9—H9 | 119.7 | O3'—S1'—O2' | 114.1 (3) |
C10—C9—C8 | 120.6 (6) | O3'—S1'—O4' | 115.4 (3) |
C10—C9—H9 | 119.7 | O3'—S1'—C4' | 104.6 (3) |
C9i—C10—C9 | 120.2 (8) | O4'—S1'—O2' | 114.2 (3) |
C9—C10—H10 | 119.9 | O4'—S1'—C4' | 103.6 (3) |
C9i—C10—H10 | 119.9 | F1'—C4'—S1' | 110.9 (5) |
C8i—C11—C8 | 120.1 (8) | F2'—C4'—S1' | 110.8 (5) |
C8—C11—H11 | 120.0 | F2'—C4'—F1' | 108.2 (7) |
C8i—C11—H11 | 120.0 | F2'—C4'—F3' | 107.8 (6) |
N1—C12—H12A | 109.5 | F3'—C4'—S1' | 111.5 (6) |
N1—C12—H12B | 109.5 | F3'—C4'—F1' | 107.6 (6) |
| | | |
I1—C2—C3—C4 | −179.7 (4) | C11—C8—C9—C10 | 0.2 (9) |
I1—C2—C3—C6 | 1.0 (8) | C12—N1—C1—C2 | −177.2 (6) |
N1—C1—C2—I1 | 179.7 (4) | C12—N1—C5—C4 | 177.9 (6) |
N1—C1—C2—C3 | −1.0 (9) | C2'—N1'—C1'—O1' | −178 (3) |
C1—N1—C5—C4 | 0.5 (9) | C3'—N1'—C1'—O1' | 4 (4) |
C1—C2—C3—C4 | 1.0 (9) | O2'—S1'—C4'—F1' | 60.1 (6) |
C1—C2—C3—C6 | −178.3 (6) | O2'—S1'—C4'—F2' | −179.8 (6) |
C2—C3—C4—C5 | −0.4 (9) | O2'—S1'—C4'—F3' | −59.7 (5) |
C3—C4—C5—N1 | −0.4 (9) | O3'—S1'—C4'—F1' | 179.5 (5) |
C5—N1—C1—C2 | 0.2 (9) | O3'—S1'—C4'—F2' | −60.4 (7) |
C6—C3—C4—C5 | 179.0 (6) | O3'—S1'—C4'—F3' | 59.7 (6) |
C7—C8—C9—C10 | −179.8 (5) | O4'—S1'—C4'—F1' | −59.2 (6) |
C7—C8—C11—C8i | 179.9 (6) | O4'—S1'—C4'—F2' | 61.0 (6) |
C8—C9—C10—C9i | −0.1 (4) | O4'—S1'—C4'—F3' | −179.0 (5) |
C9—C8—C11—C8i | −0.1 (4) | | |
Symmetry code: (i) −x+1, y, −z+3/2. |
Crystal data top
C22H16I2N2·2(CNS)·CH4O | Z = 2 |
Mr = 710.37 | F(000) = 688 |
Triclinic, P1 | Dx = 1.786 Mg m−3 |
a = 9.1203 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.3562 (14) Å | Cell parameters from 9947 reflections |
c = 13.9355 (18) Å | θ = 3.1–25.8° |
α = 77.294 (4)° | µ = 2.56 mm−1 |
β = 71.958 (4)° | T = 100 K |
γ = 77.390 (4)° | Block, yellow |
V = 1321.1 (3) Å3 | 0.15 × 0.1 × 0.05 mm |
Data collection top
Bruker D8 VENTURE Duo diffractometer | 5062 independent reflections |
Radiation source: sealed tube, fine-focus | 4063 reflections with I > 2σ(I) |
TRIUMPH graphite monochromator | Rint = 0.076 |
Detector resolution: 10.5 pixels mm-1 | θmax = 25.9°, θmin = 3.1° |
ω and φ scans | h = −11→11 |
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 = −13→13 |
Tmin = 0.252, Tmax = 0.332 | l = −17→17 |
41885 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.058 | Hydrogen site location: mixed |
wR(F2) = 0.157 | H 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 parameters | Δρmax = 3.37 e Å−3 |
0 restraints | Δρmin = −2.02 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
I1 | 0.74484 (5) | 0.06812 (4) | 0.53431 (3) | 0.02508 (17) | |
I2 | 0.18193 (5) | 0.42188 (4) | −0.15915 (3) | 0.02235 (17) | |
N1 | 0.8299 (6) | 0.3768 (5) | 0.6273 (4) | 0.0224 (12) | |
N2 | 0.0568 (6) | 0.8122 (5) | −0.1752 (4) | 0.0226 (12) | |
C1 | 0.8148 (8) | 0.2634 (6) | 0.6212 (5) | 0.0218 (14) | |
H1 | 0.8493 | 0.1949 | 0.6665 | 0.026* | |
C2 | 0.7497 (8) | 0.2463 (6) | 0.5495 (5) | 0.0222 (14) | |
C3 | 0.6951 (7) | 0.3483 (6) | 0.4842 (5) | 0.0210 (14) | |
C4 | 0.7125 (8) | 0.4645 (6) | 0.4943 (5) | 0.0232 (14) | |
H4 | 0.6785 | 0.5352 | 0.4507 | 0.028* | |
C5 | 0.7788 (8) | 0.4758 (6) | 0.5671 (5) | 0.0258 (15) | |
H5 | 0.7883 | 0.5546 | 0.5747 | 0.031* | |
C6 | 0.6284 (7) | 0.3325 (6) | 0.4093 (5) | 0.0210 (14) | |
C7 | 0.5732 (8) | 0.3131 (6) | 0.3478 (5) | 0.0225 (14) | |
C8 | 0.5095 (7) | 0.2850 (6) | 0.2752 (5) | 0.0216 (14) | |
C9 | 0.5106 (8) | 0.1631 (6) | 0.2697 (5) | 0.0256 (15) | |
H9 | 0.5544 | 0.0985 | 0.3139 | 0.031* | |
C10 | 0.4480 (8) | 0.1370 (6) | 0.2001 (5) | 0.0276 (15) | |
H10 | 0.4497 | 0.0543 | 0.1960 | 0.033* | |
C11 | 0.3822 (8) | 0.2312 (6) | 0.1358 (5) | 0.0257 (15) | |
H11 | 0.3373 | 0.2126 | 0.0890 | 0.031* | |
C12 | 0.4470 (7) | 0.3800 (6) | 0.2093 (5) | 0.0209 (14) | |
H12 | 0.4487 | 0.4626 | 0.2118 | 0.025* | |
C13 | 0.3821 (8) | 0.3530 (6) | 0.1400 (5) | 0.0245 (14) | |
C14 | 0.3161 (7) | 0.4494 (6) | 0.0743 (5) | 0.0169 (13) | |
C15 | 0.2586 (8) | 0.5313 (6) | 0.0187 (5) | 0.0254 (15) | |
C16 | 0.1906 (7) | 0.6258 (6) | −0.0480 (5) | 0.0216 (14) | |
C17 | 0.1642 (8) | 0.7477 (6) | −0.0344 (5) | 0.0272 (15) | |
H17 | 0.1912 | 0.7677 | 0.0200 | 0.033* | |
C18 | 0.0994 (8) | 0.8387 (6) | −0.0990 (5) | 0.0260 (15) | |
H18 | 0.0845 | 0.9214 | −0.0899 | 0.031* | |
C19 | 0.1443 (8) | 0.6006 (6) | −0.1281 (5) | 0.0223 (14) | |
C20 | 0.0767 (7) | 0.6954 (6) | −0.1893 (5) | 0.0201 (13) | |
H20 | 0.0435 | 0.6782 | −0.2422 | 0.024* | |
C21 | 0.9105 (9) | 0.3900 (6) | 0.7022 (6) | 0.0286 (16) | |
H21A | 0.8575 | 0.3519 | 0.7710 | 0.043* | |
H21B | 0.9071 | 0.4770 | 0.7016 | 0.043* | |
H21C | 1.0195 | 0.3497 | 0.6830 | 0.043* | |
C22 | −0.0137 (9) | 0.9120 (6) | −0.2434 (6) | 0.0282 (15) | |
H22A | −0.0316 | 0.8783 | −0.2970 | 0.042* | |
H22B | 0.0573 | 0.9720 | −0.2748 | 0.042* | |
H22C | −0.1134 | 0.9520 | −0.2034 | 0.042* | |
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'A | 0.4427 | 0.7537 | 0.2022 | 0.060* | |
H3'B | 0.4930 | 0.8360 | 0.0920 | 0.060* | |
H3'C | 0.4373 | 0.7084 | 0.1026 | 0.060* | |
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 | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.0369 (3) | 0.0195 (3) | 0.0274 (3) | −0.00819 (19) | −0.0173 (2) | −0.00561 (18) |
I2 | 0.0294 (3) | 0.0206 (3) | 0.0248 (3) | −0.00555 (18) | −0.01539 (19) | −0.00677 (18) |
N1 | 0.031 (3) | 0.022 (3) | 0.023 (3) | −0.007 (2) | −0.013 (2) | −0.009 (2) |
N2 | 0.028 (3) | 0.023 (3) | 0.022 (3) | −0.004 (2) | −0.012 (2) | −0.008 (2) |
C1 | 0.030 (4) | 0.022 (3) | 0.018 (3) | −0.008 (3) | −0.012 (3) | −0.001 (3) |
C2 | 0.027 (3) | 0.023 (3) | 0.021 (3) | −0.009 (3) | −0.009 (3) | −0.006 (3) |
C3 | 0.023 (3) | 0.027 (3) | 0.019 (3) | −0.009 (3) | −0.006 (3) | −0.009 (3) |
C4 | 0.033 (4) | 0.019 (3) | 0.024 (3) | −0.004 (3) | −0.013 (3) | −0.006 (3) |
C5 | 0.033 (4) | 0.019 (3) | 0.031 (4) | −0.004 (3) | −0.014 (3) | −0.009 (3) |
C6 | 0.027 (3) | 0.022 (3) | 0.019 (3) | −0.006 (3) | −0.011 (3) | −0.005 (3) |
C7 | 0.025 (3) | 0.024 (3) | 0.020 (3) | −0.007 (3) | −0.007 (3) | −0.002 (3) |
C8 | 0.023 (3) | 0.025 (3) | 0.023 (3) | −0.007 (3) | −0.012 (3) | −0.006 (3) |
C9 | 0.030 (4) | 0.028 (4) | 0.024 (4) | −0.006 (3) | −0.013 (3) | −0.005 (3) |
C10 | 0.034 (4) | 0.028 (4) | 0.029 (4) | −0.013 (3) | −0.012 (3) | −0.007 (3) |
C11 | 0.031 (4) | 0.035 (4) | 0.020 (3) | −0.009 (3) | −0.012 (3) | −0.012 (3) |
C12 | 0.025 (3) | 0.025 (3) | 0.018 (3) | −0.007 (3) | −0.008 (3) | −0.008 (3) |
C13 | 0.023 (3) | 0.036 (4) | 0.017 (3) | −0.005 (3) | −0.007 (3) | −0.006 (3) |
C14 | 0.018 (3) | 0.023 (3) | 0.014 (3) | −0.006 (3) | −0.003 (2) | −0.011 (3) |
C15 | 0.028 (4) | 0.032 (4) | 0.022 (3) | −0.006 (3) | −0.011 (3) | −0.009 (3) |
C16 | 0.020 (3) | 0.032 (4) | 0.017 (3) | −0.009 (3) | −0.004 (3) | −0.008 (3) |
C17 | 0.032 (4) | 0.032 (4) | 0.029 (4) | −0.010 (3) | −0.015 (3) | −0.012 (3) |
C18 | 0.033 (4) | 0.027 (4) | 0.027 (4) | −0.008 (3) | −0.012 (3) | −0.015 (3) |
C19 | 0.028 (3) | 0.022 (3) | 0.022 (3) | −0.007 (3) | −0.009 (3) | −0.007 (3) |
C20 | 0.028 (3) | 0.026 (3) | 0.012 (3) | −0.006 (3) | −0.010 (3) | −0.006 (3) |
C21 | 0.040 (4) | 0.029 (4) | 0.031 (4) | −0.009 (3) | −0.023 (3) | −0.011 (3) |
C22 | 0.039 (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—C2 | 2.092 (6) | C12—C13 | 1.393 (9) |
I2—C19 | 2.101 (6) | C13—C14 | 1.418 (9) |
N1—C1 | 1.349 (8) | C14—C15 | 1.210 (9) |
N1—C5 | 1.336 (9) | C15—C16 | 1.424 (9) |
N1—C21 | 1.498 (8) | C16—C17 | 1.398 (10) |
N2—C18 | 1.349 (8) | C16—C19 | 1.411 (9) |
N2—C20 | 1.348 (9) | C17—H17 | 0.9500 |
N2—C22 | 1.479 (9) | C17—C18 | 1.371 (10) |
C1—H1 | 0.9500 | C18—H18 | 0.9500 |
C1—C2 | 1.374 (9) | C19—C20 | 1.378 (9) |
C2—C3 | 1.408 (9) | C20—H20 | 0.9500 |
C3—C4 | 1.405 (9) | C21—H21A | 0.9800 |
C3—C6 | 1.420 (9) | C21—H21B | 0.9800 |
C4—H4 | 0.9500 | C21—H21C | 0.9800 |
C4—C5 | 1.371 (9) | C22—H22A | 0.9800 |
C5—H5 | 0.9500 | C22—H22B | 0.9800 |
C6—C7 | 1.198 (9) | C22—H22C | 0.9800 |
C7—C8 | 1.432 (9) | S2'—C2' | 1.662 (8) |
C8—C9 | 1.400 (10) | O1'—H1' | 0.88 (8) |
C8—C12 | 1.398 (9) | O1'—C3' | 1.389 (9) |
C9—H9 | 0.9500 | N2'—C2' | 1.155 (10) |
C9—C10 | 1.378 (10) | C3'—H3'A | 0.9800 |
C10—H10 | 0.9500 | C3'—H3'B | 0.9800 |
C10—C11 | 1.392 (10) | C3'—H3'C | 0.9800 |
C11—H11 | 0.9500 | S1'—C1' | 1.651 (7) |
C11—C13 | 1.397 (10) | N1'—C1' | 1.159 (9) |
C12—H12 | 0.9500 | | |
| | | |
C1—N1—C21 | 118.3 (5) | C12—C13—C14 | 119.7 (6) |
C5—N1—C1 | 121.8 (6) | C15—C14—C13 | 179.4 (7) |
C5—N1—C21 | 119.9 (5) | C14—C15—C16 | 178.7 (7) |
C18—N2—C22 | 119.6 (6) | C17—C16—C15 | 120.5 (6) |
C20—N2—C18 | 120.6 (6) | C17—C16—C19 | 117.6 (6) |
C20—N2—C22 | 119.8 (5) | C19—C16—C15 | 121.9 (6) |
N1—C1—H1 | 119.9 | C16—C17—H17 | 119.8 |
N1—C1—C2 | 120.3 (6) | C18—C17—C16 | 120.4 (6) |
C2—C1—H1 | 119.9 | C18—C17—H17 | 119.8 |
C1—C2—I1 | 119.1 (5) | N2—C18—C17 | 120.8 (6) |
C1—C2—C3 | 119.7 (6) | N2—C18—H18 | 119.6 |
C3—C2—I1 | 121.1 (5) | C17—C18—H18 | 119.6 |
C2—C3—C6 | 120.5 (6) | C16—C19—I2 | 121.5 (5) |
C4—C3—C2 | 117.8 (6) | C20—C19—I2 | 119.0 (5) |
C4—C3—C6 | 121.7 (6) | C20—C19—C16 | 119.4 (6) |
C3—C4—H4 | 120.0 | N2—C20—C19 | 121.2 (6) |
C5—C4—C3 | 119.9 (6) | N2—C20—H20 | 119.4 |
C5—C4—H4 | 120.0 | C19—C20—H20 | 119.4 |
N1—C5—C4 | 120.5 (6) | N1—C21—H21A | 109.5 |
N1—C5—H5 | 119.7 | N1—C21—H21B | 109.5 |
C4—C5—H5 | 119.7 | N1—C21—H21C | 109.5 |
C7—C6—C3 | 176.7 (7) | H21A—C21—H21B | 109.5 |
C6—C7—C8 | 177.8 (7) | H21A—C21—H21C | 109.5 |
C9—C8—C7 | 120.3 (6) | H21B—C21—H21C | 109.5 |
C12—C8—C7 | 119.5 (6) | N2—C22—H22A | 109.5 |
C12—C8—C9 | 120.1 (6) | N2—C22—H22B | 109.5 |
C8—C9—H9 | 120.1 | N2—C22—H22C | 109.5 |
C10—C9—C8 | 119.9 (6) | H22A—C22—H22B | 109.5 |
C10—C9—H9 | 120.1 | H22A—C22—H22C | 109.5 |
C9—C10—H10 | 119.8 | H22B—C22—H22C | 109.5 |
C9—C10—C11 | 120.3 (6) | C3'—O1'—H1' | 114 (5) |
C11—C10—H10 | 119.8 | N2'—C2'—S2' | 178.9 (7) |
C10—C11—H11 | 119.9 | O1'—C3'—H3'A | 109.5 |
C10—C11—C13 | 120.2 (6) | O1'—C3'—H3'B | 109.5 |
C13—C11—H11 | 119.9 | O1'—C3'—H3'C | 109.5 |
C8—C12—H12 | 120.2 | H3'A—C3'—H3'B | 109.5 |
C13—C12—C8 | 119.7 (6) | H3'A—C3'—H3'C | 109.5 |
C13—C12—H12 | 120.2 | H3'B—C3'—H3'C | 109.5 |
C11—C13—C14 | 120.5 (6) | N1'—C1'—S1' | 176.9 (6) |
C12—C13—C11 | 119.8 (6) | | |
| | | |
I1—C2—C3—C4 | −175.5 (5) | C9—C10—C11—C13 | 1.3 (11) |
I1—C2—C3—C6 | 2.9 (9) | C10—C11—C13—C12 | −0.5 (10) |
I2—C19—C20—N2 | −176.9 (5) | C10—C11—C13—C14 | 179.6 (6) |
N1—C1—C2—I1 | 175.1 (5) | C12—C8—C9—C10 | −0.9 (10) |
N1—C1—C2—C3 | −1.7 (10) | C15—C16—C17—C18 | 179.6 (6) |
C1—N1—C5—C4 | −1.9 (10) | C15—C16—C19—I2 | −2.8 (9) |
C1—C2—C3—C4 | 1.2 (10) | C15—C16—C19—C20 | 178.9 (6) |
C1—C2—C3—C6 | 179.6 (6) | C16—C17—C18—N2 | 1.5 (11) |
C2—C3—C4—C5 | −1.0 (10) | C16—C19—C20—N2 | 1.4 (10) |
C3—C4—C5—N1 | 1.4 (10) | C17—C16—C19—I2 | 178.6 (5) |
C5—N1—C1—C2 | 2.0 (10) | C17—C16—C19—C20 | 0.3 (9) |
C6—C3—C4—C5 | −179.4 (6) | C18—N2—C20—C19 | −1.7 (10) |
C7—C8—C9—C10 | 179.5 (6) | C19—C16—C17—C18 | −1.7 (10) |
C7—C8—C12—C13 | −178.7 (6) | C20—N2—C18—C17 | 0.2 (10) |
C8—C9—C10—C11 | −0.6 (11) | C21—N1—C1—C2 | −176.3 (6) |
C8—C12—C13—C11 | −1.0 (10) | C21—N1—C5—C4 | 176.4 (6) |
C8—C12—C13—C14 | 178.9 (6) | C22—N2—C18—C17 | 179.6 (7) |
C9—C8—C12—C13 | 1.7 (10) | C22—N2—C20—C19 | 179.0 (6) |
Crystal data top
C22H16I2N2·0.97(CH2Cl2)·2(CNS) | Z = 2 |
Mr = 760.71 | F(000) = 733 |
Triclinic, P1 | Dx = 1.837 Mg m−3 |
a = 7.7270 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.9671 (4) Å | Cell parameters from 9372 reflections |
c = 16.9780 (7) Å | θ = 3.1–28.8° |
α = 103.375 (2)° | µ = 2.65 mm−1 |
β = 98.725 (2)° | T = 100 K |
γ = 94.093 (2)° | Rod, yellow |
V = 1375.03 (9) Å3 | 0.5 × 0.05 × 0.02 mm |
Data collection top
Bruker D8 VENTURE Duo diffractometer | 6282 independent reflections |
Radiation source: sealed tube, fine-focus | 5184 reflections with I > 2σ(I) |
TRIUMPH graphite monochromator | Rint = 0.072 |
Detector resolution: 10.5 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
φ and ω scans | h = −10→10 |
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 = −14→14 |
Tmin = 0.266, Tmax = 0.335 | l = −22→22 |
105156 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.064 | H-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 parameters | Δρmax = 1.01 e Å−3 |
0 restraints | Δρmin = −0.65 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
I1 | 0.18696 (3) | 0.86748 (2) | 0.50650 (2) | 0.01936 (7) | 0.9689 (9) |
I2 | 0.54771 (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) |
N1 | −0.0012 (4) | 0.9647 (3) | 0.73683 (17) | 0.0212 (6) | |
N2 | 0.6731 (4) | 0.3021 (3) | 0.03692 (17) | 0.0206 (6) | |
C1 | 0.0522 (4) | 0.9661 (3) | 0.6649 (2) | 0.0198 (7) | |
H1 | 0.0570 | 1.0424 | 0.6475 | 0.024* | |
C2 | 0.0999 (4) | 0.8588 (3) | 0.61618 (19) | 0.0177 (7) | |
H2 | 0.1354 | 0.8605 | 0.5652 | 0.021* | 0.0311 (9) |
C3 | 0.0951 (4) | 0.7465 (3) | 0.64334 (19) | 0.0175 (6) | |
C4 | 0.0365 (4) | 0.7488 (3) | 0.7180 (2) | 0.0208 (7) | |
H4 | 0.0294 | 0.6741 | 0.7372 | 0.025* | 0.9689 (9) |
C5 | −0.0104 (4) | 0.8577 (3) | 0.7634 (2) | 0.0214 (7) | |
H5 | −0.0496 | 0.8582 | 0.8138 | 0.026* | |
C6 | 0.1500 (4) | 0.6348 (3) | 0.5982 (2) | 0.0188 (7) | |
C7 | 0.2008 (4) | 0.5417 (3) | 0.56097 (19) | 0.0180 (7) | |
C8 | 0.2620 (4) | 0.4311 (3) | 0.51513 (19) | 0.0170 (6) | |
C9 | 0.2802 (4) | 0.3254 (3) | 0.5475 (2) | 0.0224 (7) | |
H9 | 0.2543 | 0.3273 | 0.6007 | 0.027* | |
C10 | 0.3357 (4) | 0.2184 (3) | 0.5023 (2) | 0.0248 (7) | |
H10 | 0.3473 | 0.1467 | 0.5244 | 0.030* | |
C11 | 0.3747 (4) | 0.2152 (3) | 0.4248 (2) | 0.0218 (7) | |
H11 | 0.4094 | 0.1405 | 0.3933 | 0.026* | |
C12 | 0.3055 (4) | 0.4302 (3) | 0.4380 (2) | 0.0177 (6) | |
H12 | 0.2961 | 0.5025 | 0.4165 | 0.021* | |
C13 | 0.3630 (4) | 0.3217 (3) | 0.3930 (2) | 0.0201 (7) | |
C14 | 0.4124 (4) | 0.3185 (3) | 0.3145 (2) | 0.0217 (7) | |
C15 | 0.4606 (4) | 0.3113 (3) | 0.2505 (2) | 0.0217 (7) | |
C16 | 0.5301 (4) | 0.3067 (3) | 0.1768 (2) | 0.0188 (7) | |
C17 | 0.5584 (4) | 0.4162 (3) | 0.1501 (2) | 0.0234 (7) | |
H17 | 0.5288 | 0.4938 | 0.1803 | 0.028* | |
C18 | 0.6290 (4) | 0.4120 (3) | 0.0802 (2) | 0.0248 (8) | |
H18 | 0.6470 | 0.4868 | 0.0620 | 0.030* | |
C19 | 0.5763 (4) | 0.1935 (3) | 0.13068 (19) | 0.0166 (6) | |
C20 | 0.6489 (4) | 0.1940 (3) | 0.0611 (2) | 0.0188 (7) | |
H20 | 0.6819 | 0.1180 | 0.0302 | 0.023* | |
C21 | −0.0358 (5) | 1.0845 (4) | 0.7904 (2) | 0.0315 (9) | |
H21A | 0.0712 | 1.1443 | 0.8050 | 0.047* | |
H21B | −0.0707 | 1.0683 | 0.8405 | 0.047* | |
H21C | −0.1309 | 1.1202 | 0.7610 | 0.047* | |
C22 | 0.7459 (5) | 0.3008 (4) | −0.0387 (2) | 0.0309 (9) | |
H22A | 0.6506 | 0.2761 | −0.0864 | 0.046* | |
H22B | 0.8333 | 0.2403 | −0.0443 | 0.046* | |
H22C | 0.8021 | 0.3852 | −0.0356 | 0.046* | |
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) | |
I1A | 0.0025 (13) | 0.5791 (11) | 0.7600 (6) | 0.053 (3) | 0.0311 (9) |
C0AA | 0.0672 (5) | 0.5952 (3) | 0.1930 (2) | 0.0301 (9) | 0.9689 (9) |
H0AA | 0.1804 | 0.6494 | 0.2031 | 0.036* | 0.9689 (9) |
H0AB | −0.0217 | 0.6315 | 0.1594 | 0.036* | 0.9689 (9) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.01733 (12) | 0.02435 (13) | 0.01905 (12) | 0.00475 (9) | 0.00552 (9) | 0.00840 (9) |
I2 | 0.01878 (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) |
N1 | 0.0159 (14) | 0.0264 (15) | 0.0184 (14) | 0.0042 (11) | 0.0023 (11) | −0.0003 (12) |
N2 | 0.0178 (14) | 0.0271 (15) | 0.0166 (14) | −0.0037 (11) | 0.0026 (11) | 0.0072 (12) |
C1 | 0.0165 (16) | 0.0224 (17) | 0.0194 (17) | 0.0017 (13) | 0.0009 (13) | 0.0049 (13) |
C2 | 0.0121 (15) | 0.0230 (17) | 0.0163 (16) | 0.0017 (12) | −0.0001 (12) | 0.0033 (13) |
C3 | 0.0112 (15) | 0.0208 (16) | 0.0180 (16) | −0.0011 (12) | −0.0001 (12) | 0.0019 (13) |
C4 | 0.0171 (16) | 0.0228 (17) | 0.0208 (17) | −0.0035 (13) | 0.0009 (13) | 0.0053 (14) |
C5 | 0.0173 (16) | 0.0298 (18) | 0.0155 (16) | −0.0001 (14) | 0.0028 (13) | 0.0029 (14) |
C6 | 0.0144 (16) | 0.0242 (17) | 0.0172 (16) | −0.0023 (13) | 0.0009 (13) | 0.0065 (14) |
C7 | 0.0130 (15) | 0.0238 (17) | 0.0161 (16) | −0.0027 (13) | 0.0017 (13) | 0.0051 (13) |
C8 | 0.0108 (15) | 0.0210 (16) | 0.0173 (16) | 0.0006 (12) | 0.0017 (12) | 0.0015 (13) |
C9 | 0.0179 (17) | 0.0299 (19) | 0.0198 (17) | 0.0007 (14) | 0.0017 (13) | 0.0089 (14) |
C10 | 0.0201 (17) | 0.0219 (17) | 0.033 (2) | 0.0032 (13) | 0.0008 (15) | 0.0104 (15) |
C11 | 0.0158 (16) | 0.0197 (17) | 0.0269 (18) | 0.0039 (13) | 0.0002 (14) | 0.0015 (14) |
C12 | 0.0115 (15) | 0.0199 (16) | 0.0193 (17) | 0.0000 (12) | −0.0011 (12) | 0.0033 (13) |
C13 | 0.0108 (15) | 0.0266 (18) | 0.0202 (17) | −0.0010 (13) | −0.0003 (13) | 0.0033 (14) |
C14 | 0.0125 (15) | 0.0240 (17) | 0.0241 (18) | 0.0003 (13) | −0.0006 (13) | −0.0004 (14) |
C15 | 0.0143 (16) | 0.0246 (18) | 0.0231 (18) | 0.0026 (13) | 0.0018 (14) | 0.0002 (14) |
C16 | 0.0131 (15) | 0.0230 (17) | 0.0175 (16) | −0.0014 (12) | −0.0010 (13) | 0.0028 (13) |
C17 | 0.0196 (17) | 0.0184 (17) | 0.0292 (19) | −0.0007 (13) | 0.0013 (14) | 0.0028 (14) |
C18 | 0.0214 (18) | 0.0205 (17) | 0.032 (2) | −0.0037 (14) | −0.0034 (15) | 0.0120 (15) |
C19 | 0.0144 (15) | 0.0177 (16) | 0.0168 (16) | −0.0014 (12) | −0.0007 (12) | 0.0053 (13) |
C20 | 0.0178 (16) | 0.0169 (16) | 0.0201 (17) | −0.0018 (12) | 0.0009 (13) | 0.0039 (13) |
C21 | 0.031 (2) | 0.033 (2) | 0.026 (2) | 0.0095 (16) | 0.0037 (16) | −0.0013 (16) |
C22 | 0.035 (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) |
I1A | 0.035 (5) | 0.073 (8) | 0.048 (6) | 0.013 (5) | −0.002 (4) | 0.016 (5) |
C0AA | 0.039 (2) | 0.024 (2) | 0.028 (2) | −0.0001 (16) | 0.0109 (17) | 0.0053 (16) |
Geometric parameters (Å, º) top
I1—C2 | 2.093 (3) | C10—C11 | 1.387 (5) |
I2—C19 | 2.100 (3) | C11—H11 | 0.9500 |
Cl1'—C0AA | 1.769 (4) | C11—C13 | 1.399 (5) |
Cl2'—C0AA | 1.764 (4) | C12—H12 | 0.9500 |
N1—C1 | 1.349 (4) | C12—C13 | 1.398 (5) |
N1—C5 | 1.352 (4) | C13—C14 | 1.434 (5) |
N1—C21 | 1.482 (4) | C14—C15 | 1.189 (5) |
N2—C18 | 1.354 (5) | C15—C16 | 1.427 (5) |
N2—C20 | 1.351 (4) | C16—C17 | 1.392 (5) |
N2—C22 | 1.475 (4) | C16—C19 | 1.407 (5) |
C1—H1 | 0.9500 | C17—H17 | 0.9500 |
C1—C2 | 1.383 (5) | C17—C18 | 1.373 (5) |
C2—H2 | 0.9500 | C18—H18 | 0.9500 |
C2—C3 | 1.411 (5) | C19—C20 | 1.383 (4) |
C3—C4 | 1.405 (5) | C20—H20 | 0.9500 |
C3—C6 | 1.416 (5) | C21—H21A | 0.9800 |
C4—H4 | 0.9500 | C21—H21B | 0.9800 |
C4—C5 | 1.368 (5) | C21—H21C | 0.9800 |
C4—I1A | 2.154 (12) | C22—H22A | 0.9800 |
C5—H5 | 0.9500 | C22—H22B | 0.9800 |
C6—C7 | 1.196 (5) | C22—H22C | 0.9800 |
C7—C8 | 1.435 (5) | S1'—C1' | 1.662 (4) |
C8—C9 | 1.400 (5) | N1'—C1' | 1.158 (5) |
C8—C12 | 1.398 (4) | S2'—C2' | 1.682 (4) |
C9—H9 | 0.9500 | N2'—C2' | 1.093 (5) |
C9—C10 | 1.380 (5) | C0AA—H0AA | 0.9900 |
C10—H10 | 0.9500 | C0AA—H0AB | 0.9900 |
| | | |
C1—N1—C5 | 120.9 (3) | C13—C12—H12 | 120.4 |
C1—N1—C21 | 119.3 (3) | C11—C13—C14 | 119.3 (3) |
C5—N1—C21 | 119.6 (3) | C12—C13—C11 | 120.0 (3) |
C18—N2—C22 | 119.0 (3) | C12—C13—C14 | 120.7 (3) |
C20—N2—C18 | 121.2 (3) | C15—C14—C13 | 176.1 (4) |
C20—N2—C22 | 119.8 (3) | C14—C15—C16 | 176.0 (4) |
N1—C1—H1 | 119.3 | C17—C16—C15 | 120.2 (3) |
N1—C1—C2 | 121.3 (3) | C17—C16—C19 | 118.4 (3) |
C2—C1—H1 | 119.3 | C19—C16—C15 | 121.4 (3) |
C1—C2—I1 | 119.6 (2) | C16—C17—H17 | 120.0 |
C1—C2—H2 | 120.5 | C18—C17—C16 | 120.1 (3) |
C1—C2—C3 | 118.9 (3) | C18—C17—H17 | 120.0 |
C3—C2—I1 | 121.4 (2) | N2—C18—C17 | 120.5 (3) |
C3—C2—H2 | 120.5 | N2—C18—H18 | 119.7 |
C2—C3—C6 | 121.7 (3) | C17—C18—H18 | 119.7 |
C4—C3—C2 | 117.9 (3) | C16—C19—I2 | 121.4 (2) |
C4—C3—C6 | 120.4 (3) | C20—C19—I2 | 119.0 (2) |
C3—C4—H4 | 119.7 | C20—C19—C16 | 119.6 (3) |
C3—C4—I1A | 120.9 (4) | N2—C20—C19 | 120.3 (3) |
C5—C4—C3 | 120.6 (3) | N2—C20—H20 | 119.9 |
C5—C4—H4 | 119.7 | C19—C20—H20 | 119.9 |
C5—C4—I1A | 118.4 (4) | N1—C21—H21A | 109.5 |
N1—C5—C4 | 120.4 (3) | N1—C21—H21B | 109.5 |
N1—C5—H5 | 119.8 | N1—C21—H21C | 109.5 |
C4—C5—H5 | 119.8 | H21A—C21—H21B | 109.5 |
C7—C6—C3 | 178.3 (4) | H21A—C21—H21C | 109.5 |
C6—C7—C8 | 179.0 (3) | H21B—C21—H21C | 109.5 |
C9—C8—C7 | 120.5 (3) | N2—C22—H22A | 109.5 |
C12—C8—C7 | 119.4 (3) | N2—C22—H22B | 109.5 |
C12—C8—C9 | 120.1 (3) | N2—C22—H22C | 109.5 |
C8—C9—H9 | 119.9 | H22A—C22—H22B | 109.5 |
C10—C9—C8 | 120.2 (3) | H22A—C22—H22C | 109.5 |
C10—C9—H9 | 119.9 | H22B—C22—H22C | 109.5 |
C9—C10—H10 | 119.9 | N1'—C1'—S1' | 178.0 (3) |
C9—C10—C11 | 120.2 (3) | N2'—C2'—S2' | 177.3 (4) |
C11—C10—H10 | 119.9 | Cl1'—C0AA—H0AA | 109.2 |
C10—C11—H11 | 119.9 | Cl1'—C0AA—H0AB | 109.2 |
C10—C11—C13 | 120.2 (3) | Cl2'—C0AA—Cl1' | 112.0 (2) |
C13—C11—H11 | 119.9 | Cl2'—C0AA—H0AA | 109.2 |
C8—C12—H12 | 120.4 | Cl2'—C0AA—H0AB | 109.2 |
C8—C12—C13 | 119.3 (3) | H0AA—C0AA—H0AB | 107.9 |
| | | |
I1—C2—C3—C4 | 179.4 (2) | C9—C10—C11—C13 | 1.9 (5) |
I1—C2—C3—C6 | 0.5 (4) | C10—C11—C13—C12 | −2.4 (5) |
I2—C19—C20—N2 | −178.3 (2) | C10—C11—C13—C14 | 176.9 (3) |
N1—C1—C2—I1 | −178.7 (2) | C12—C8—C9—C10 | −2.1 (5) |
N1—C1—C2—C3 | −1.0 (5) | C15—C16—C17—C18 | 178.6 (3) |
C1—N1—C5—C4 | 0.8 (5) | C15—C16—C19—I2 | −0.5 (4) |
C1—C2—C3—C4 | 1.8 (4) | C15—C16—C19—C20 | −177.8 (3) |
C1—C2—C3—C6 | −177.1 (3) | C16—C17—C18—N2 | −0.6 (5) |
C2—C3—C4—C5 | −1.4 (5) | C16—C19—C20—N2 | −0.9 (5) |
C2—C3—C4—I1A | 174.7 (4) | C17—C16—C19—I2 | 177.8 (2) |
C3—C4—C5—N1 | 0.1 (5) | C17—C16—C19—C20 | 0.5 (5) |
C5—N1—C1—C2 | −0.3 (5) | C18—N2—C20—C19 | 0.7 (5) |
C6—C3—C4—C5 | 177.5 (3) | C19—C16—C17—C18 | 0.3 (5) |
C6—C3—C4—I1A | −6.4 (5) | C20—N2—C18—C17 | 0.1 (5) |
C7—C8—C9—C10 | 178.7 (3) | C21—N1—C1—C2 | 174.6 (3) |
C7—C8—C12—C13 | −179.2 (3) | C21—N1—C5—C4 | −174.1 (3) |
C8—C9—C10—C11 | 0.3 (5) | C22—N2—C18—C17 | 179.0 (3) |
C8—C12—C13—C11 | 0.7 (5) | C22—N2—C20—C19 | −178.2 (3) |
C8—C12—C13—C14 | −178.6 (3) | I1A—C4—C5—N1 | −176.0 (4) |
C9—C8—C12—C13 | 1.6 (5) | | |
Crystal data top
C22H16I2N2·2(I3) | F(000) = 2344 |
Mr = 1323.57 | Dx = 2.725 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54178 Å |
a = 7.3983 (4) Å | Cell parameters from 9877 reflections |
b = 10.4370 (5) Å | θ = 4.2–58.9° |
c = 41.8567 (18) Å | µ = 60.50 mm−1 |
β = 93.424 (2)° | T = 100 K |
V = 3226.2 (3) Å3 | Plate, yellow |
Z = 4 | 0.5 × 0.05 × 0.05 mm |
Data collection top
Bruker D8 VENTURE Duo diffractometer | 4551 independent reflections |
Radiation source: microfocus sealed X-ray tube, Incoatec Iµus | 3685 reflections with I > 2σ(I) |
Double Bounce Multilayer Mirror monochromator | Rint = 0.066 |
Detector resolution: 10.5 pixels mm-1 | θmax = 59.0°, θmin = 2.1° |
ω and φ scans | h = −7→7 |
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 = −11→11 |
Tmin = 0.010, Tmax = 0.097 | l = −45→45 |
26322 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-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 reflections | Δρmax = 1.05 e Å−3 |
291 parameters | Δρmin = −0.64 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
I1 | 0.61011 (11) | 0.23036 (7) | 0.33918 (2) | 0.0561 (2) | |
I2 | 0.08369 (11) | 0.38641 (7) | 0.60206 (2) | 0.0561 (2) | |
N1 | 0.5933 (14) | 0.5954 (9) | 0.2929 (2) | 0.055 (2) | |
N2 | −0.0466 (13) | 0.7840 (8) | 0.6094 (2) | 0.052 (2) | |
C1 | 0.6184 (15) | 0.4707 (10) | 0.3005 (3) | 0.047 (2) | |
H1 | 0.6720 | 0.4149 | 0.2858 | 0.056* | |
C2 | 0.5679 (16) | 0.4246 (10) | 0.3288 (3) | 0.048 (2) | |
C3 | 0.4955 (15) | 0.5063 (11) | 0.3510 (3) | 0.051 (2) | |
C4 | 0.4729 (17) | 0.6350 (11) | 0.3421 (3) | 0.057 (3) | |
H4 | 0.4229 | 0.6936 | 0.3565 | 0.069* | |
C5 | 0.5212 (17) | 0.6773 (12) | 0.3132 (3) | 0.057 (3) | |
H5 | 0.5041 | 0.7647 | 0.3075 | 0.068* | |
C6 | 0.4529 (16) | 0.4648 (11) | 0.3821 (3) | 0.054 (3) | |
C7 | 0.4254 (17) | 0.4304 (10) | 0.4089 (3) | 0.052 (3) | |
C8 | 0.3913 (15) | 0.3849 (10) | 0.4398 (3) | 0.049 (2) | |
C9 | 0.4310 (14) | 0.2554 (10) | 0.4476 (3) | 0.048 (2) | |
H9 | 0.4801 | 0.2009 | 0.4321 | 0.057* | |
C10 | 0.3986 (17) | 0.2078 (12) | 0.4776 (3) | 0.059 (3) | |
H10 | 0.4248 | 0.1209 | 0.4829 | 0.071* | |
C11 | 0.3275 (16) | 0.2886 (10) | 0.5000 (3) | 0.054 (3) | |
H11 | 0.3057 | 0.2563 | 0.5206 | 0.065* | |
C12 | 0.3202 (15) | 0.4629 (11) | 0.4633 (3) | 0.050 (3) | |
H12 | 0.2940 | 0.5504 | 0.4587 | 0.060* | |
C13 | 0.2883 (15) | 0.4131 (10) | 0.4930 (3) | 0.049 (2) | |
C14 | 0.2213 (16) | 0.4950 (11) | 0.5171 (3) | 0.052 (3) | |
C15 | 0.1658 (16) | 0.5584 (11) | 0.5382 (3) | 0.050 (3) | |
C16 | 0.0939 (16) | 0.6344 (10) | 0.5628 (3) | 0.048 (2) | |
C17 | 0.0684 (16) | 0.7667 (11) | 0.5588 (3) | 0.054 (3) | |
H17 | 0.1000 | 0.8065 | 0.5395 | 0.065* | |
C18 | −0.0016 (16) | 0.8388 (11) | 0.5823 (3) | 0.051 (3) | |
H18 | −0.0182 | 0.9284 | 0.5794 | 0.061* | |
C19 | 0.0480 (15) | 0.5817 (10) | 0.5921 (2) | 0.046 (2) | |
C20 | −0.0243 (15) | 0.6585 (10) | 0.6150 (2) | 0.044 (2) | |
H20 | −0.0579 | 0.6225 | 0.6346 | 0.053* | |
C21 | 0.6520 (19) | 0.6441 (12) | 0.2618 (3) | 0.063 (3) | |
H21A | 0.7824 | 0.6303 | 0.2606 | 0.095* | |
H21B | 0.6254 | 0.7359 | 0.2600 | 0.095* | |
H21C | 0.5867 | 0.5982 | 0.2442 | 0.095* | |
C22 | −0.1224 (18) | 0.8630 (11) | 0.6349 (3) | 0.057 (3) | |
H22A | −0.1526 | 0.8076 | 0.6528 | 0.085* | |
H22B | −0.2320 | 0.9067 | 0.6263 | 0.085* | |
H22C | −0.0326 | 0.9268 | 0.6426 | 0.085* | |
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 | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.0568 (5) | 0.0469 (4) | 0.0644 (5) | −0.0012 (3) | 0.0025 (4) | 0.0031 (3) |
I2 | 0.0685 (6) | 0.0438 (4) | 0.0551 (5) | −0.0044 (4) | −0.0032 (4) | 0.0016 (3) |
N1 | 0.067 (6) | 0.053 (4) | 0.046 (4) | 0.000 (4) | −0.003 (4) | 0.009 (3) |
N2 | 0.063 (6) | 0.044 (4) | 0.049 (4) | −0.005 (4) | −0.001 (4) | −0.002 (3) |
C1 | 0.042 (6) | 0.048 (4) | 0.049 (5) | −0.005 (4) | −0.003 (4) | 0.000 (4) |
C2 | 0.054 (7) | 0.047 (5) | 0.043 (4) | −0.006 (4) | −0.006 (4) | 0.002 (3) |
C3 | 0.049 (6) | 0.049 (4) | 0.053 (5) | −0.007 (4) | −0.002 (4) | −0.002 (3) |
C4 | 0.067 (8) | 0.050 (5) | 0.054 (5) | −0.005 (5) | 0.003 (5) | −0.002 (4) |
C5 | 0.063 (7) | 0.054 (5) | 0.053 (5) | −0.001 (5) | −0.003 (5) | 0.004 (4) |
C6 | 0.052 (7) | 0.057 (6) | 0.052 (4) | −0.011 (5) | −0.005 (4) | −0.006 (4) |
C7 | 0.061 (8) | 0.042 (5) | 0.054 (4) | −0.010 (5) | 0.000 (4) | −0.010 (4) |
C8 | 0.046 (6) | 0.048 (5) | 0.052 (4) | 0.003 (4) | 0.001 (4) | −0.005 (3) |
C9 | 0.034 (6) | 0.050 (5) | 0.058 (5) | −0.002 (4) | −0.007 (4) | −0.007 (4) |
C10 | 0.060 (8) | 0.054 (5) | 0.063 (5) | 0.003 (5) | −0.003 (5) | −0.003 (4) |
C11 | 0.064 (7) | 0.042 (4) | 0.055 (5) | −0.005 (4) | 0.004 (5) | 0.001 (4) |
C12 | 0.050 (7) | 0.047 (5) | 0.052 (4) | 0.002 (4) | 0.000 (4) | −0.001 (4) |
C13 | 0.048 (6) | 0.046 (4) | 0.053 (5) | −0.005 (4) | 0.001 (4) | −0.003 (3) |
C14 | 0.059 (7) | 0.046 (5) | 0.051 (5) | −0.004 (5) | 0.002 (5) | 0.002 (4) |
C15 | 0.048 (6) | 0.057 (6) | 0.043 (5) | 0.000 (5) | −0.012 (4) | 0.001 (4) |
C16 | 0.052 (7) | 0.050 (4) | 0.042 (4) | −0.003 (4) | −0.005 (4) | 0.001 (3) |
C17 | 0.063 (7) | 0.053 (5) | 0.046 (5) | −0.001 (4) | 0.001 (5) | 0.006 (4) |
C18 | 0.058 (7) | 0.044 (5) | 0.049 (5) | −0.004 (4) | −0.004 (4) | 0.006 (4) |
C19 | 0.051 (6) | 0.043 (4) | 0.042 (4) | −0.005 (4) | −0.004 (4) | 0.001 (3) |
C20 | 0.051 (6) | 0.044 (4) | 0.038 (5) | −0.006 (4) | −0.004 (4) | 0.004 (3) |
C21 | 0.074 (8) | 0.068 (7) | 0.047 (5) | −0.005 (6) | −0.005 (5) | 0.011 (5) |
C22 | 0.076 (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—C2 | 2.093 (11) | C11—H11 | 0.9500 |
I2—C19 | 2.094 (11) | C11—C13 | 1.360 (15) |
N1—C1 | 1.350 (14) | C12—H12 | 0.9500 |
N1—C5 | 1.340 (15) | C12—C13 | 1.382 (15) |
N1—C21 | 1.486 (14) | C13—C14 | 1.433 (16) |
N2—C18 | 1.328 (14) | C14—C15 | 1.197 (15) |
N2—C20 | 1.339 (14) | C15—C16 | 1.429 (16) |
N2—C22 | 1.487 (14) | C16—C17 | 1.402 (15) |
C1—H1 | 0.9500 | C16—C19 | 1.402 (15) |
C1—C2 | 1.352 (15) | C17—H17 | 0.9500 |
C2—C3 | 1.393 (15) | C17—C18 | 1.367 (16) |
C3—C4 | 1.402 (16) | C18—H18 | 0.9500 |
C3—C6 | 1.425 (16) | C19—C20 | 1.383 (15) |
C4—H4 | 0.9500 | C20—H20 | 0.9500 |
C4—C5 | 1.353 (16) | C21—H21A | 0.9800 |
C5—H5 | 0.9500 | C21—H21B | 0.9800 |
C6—C7 | 1.204 (15) | C21—H21C | 0.9800 |
C7—C8 | 1.416 (16) | C22—H22A | 0.9800 |
C8—C9 | 1.417 (15) | C22—H22B | 0.9800 |
C8—C12 | 1.402 (15) | C22—H22C | 0.9800 |
C9—H9 | 0.9500 | I4'—I5' | 2.9755 (10) |
C9—C10 | 1.388 (16) | I5'—I6' | 2.8681 (11) |
C10—H10 | 0.9500 | I1'—I2' | 2.9781 (11) |
C10—C11 | 1.386 (16) | I2'—I3' | 2.8464 (11) |
| | | |
C1—N1—C21 | 119.5 (10) | C13—C12—C8 | 120.2 (11) |
C5—N1—C1 | 121.3 (10) | C13—C12—H12 | 119.9 |
C5—N1—C21 | 119.2 (10) | C11—C13—C12 | 120.5 (11) |
C18—N2—C20 | 122.5 (10) | C11—C13—C14 | 119.8 (11) |
C18—N2—C22 | 119.9 (9) | C12—C13—C14 | 119.6 (10) |
C20—N2—C22 | 117.6 (9) | C15—C14—C13 | 176.8 (12) |
N1—C1—H1 | 119.7 | C14—C15—C16 | 178.1 (13) |
N1—C1—C2 | 120.6 (11) | C17—C16—C15 | 120.9 (10) |
C2—C1—H1 | 119.7 | C19—C16—C15 | 122.1 (10) |
C1—C2—I1 | 118.8 (8) | C19—C16—C17 | 117.0 (10) |
C1—C2—C3 | 120.3 (10) | C16—C17—H17 | 119.7 |
C3—C2—I1 | 120.8 (8) | C18—C17—C16 | 120.6 (11) |
C2—C3—C4 | 117.0 (11) | C18—C17—H17 | 119.7 |
C2—C3—C6 | 122.7 (10) | N2—C18—C17 | 120.2 (10) |
C4—C3—C6 | 120.3 (11) | N2—C18—H18 | 119.9 |
C3—C4—H4 | 119.4 | C17—C18—H18 | 119.9 |
C5—C4—C3 | 121.1 (12) | C16—C19—I2 | 121.5 (8) |
C5—C4—H4 | 119.4 | C20—C19—I2 | 118.3 (8) |
N1—C5—C4 | 119.7 (11) | C20—C19—C16 | 120.2 (10) |
N1—C5—H5 | 120.1 | N2—C20—C19 | 119.5 (10) |
C4—C5—H5 | 120.1 | N2—C20—H20 | 120.2 |
C7—C6—C3 | 176.9 (13) | C19—C20—H20 | 120.2 |
C6—C7—C8 | 177.7 (12) | N1—C21—H21A | 109.5 |
C7—C8—C9 | 118.9 (10) | N1—C21—H21B | 109.5 |
C12—C8—C7 | 122.8 (10) | N1—C21—H21C | 109.5 |
C12—C8—C9 | 118.3 (10) | H21A—C21—H21B | 109.5 |
C8—C9—H9 | 119.8 | H21A—C21—H21C | 109.5 |
C10—C9—C8 | 120.3 (11) | H21B—C21—H21C | 109.5 |
C10—C9—H9 | 119.8 | N2—C22—H22A | 109.5 |
C9—C10—H10 | 120.4 | N2—C22—H22B | 109.5 |
C11—C10—C9 | 119.2 (11) | N2—C22—H22C | 109.5 |
C11—C10—H10 | 120.4 | H22A—C22—H22B | 109.5 |
C10—C11—H11 | 119.3 | H22A—C22—H22C | 109.5 |
C13—C11—C10 | 121.4 (11) | H22B—C22—H22C | 109.5 |
C13—C11—H11 | 119.3 | I6'—I5'—I4' | 176.56 (3) |
C8—C12—H12 | 119.9 | I3'—I2'—I1' | 176.98 (4) |
| | | |
I1—C2—C3—C4 | 179.6 (9) | C9—C10—C11—C13 | 0.3 (18) |
I1—C2—C3—C6 | 2.5 (16) | C10—C11—C13—C12 | −0.6 (19) |
I2—C19—C20—N2 | 179.2 (8) | C10—C11—C13—C14 | −177.7 (11) |
N1—C1—C2—I1 | 179.9 (8) | C12—C8—C9—C10 | 0.5 (17) |
N1—C1—C2—C3 | −2.4 (17) | C15—C16—C17—C18 | 179.5 (11) |
C1—N1—C5—C4 | 0.3 (18) | C15—C16—C19—I2 | 0.5 (16) |
C1—C2—C3—C4 | 2.1 (17) | C15—C16—C19—C20 | −178.8 (11) |
C1—C2—C3—C6 | −175.1 (11) | C16—C17—C18—N2 | −0.1 (18) |
C2—C3—C4—C5 | −0.6 (18) | C16—C19—C20—N2 | −1.4 (17) |
C3—C4—C5—N1 | −0.6 (19) | C17—C16—C19—I2 | −178.7 (8) |
C5—N1—C1—C2 | 1.2 (17) | C17—C16—C19—C20 | 1.9 (17) |
C6—C3—C4—C5 | 176.6 (12) | C18—N2—C20—C19 | 0.0 (17) |
C7—C8—C9—C10 | −179.8 (11) | C19—C16—C17—C18 | −1.2 (18) |
C7—C8—C12—C13 | 179.5 (11) | C20—N2—C18—C17 | 0.8 (18) |
C8—C9—C10—C11 | −0.2 (17) | C21—N1—C1—C2 | 179.3 (11) |
C8—C12—C13—C11 | 0.9 (18) | C21—N1—C5—C4 | −177.8 (12) |
C8—C12—C13—C14 | 178.0 (11) | C22—N2—C18—C17 | 179.9 (11) |
C9—C8—C12—C13 | −0.8 (17) | C22—N2—C20—C19 | −179.2 (10) |