Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680001761X/na6000sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680001761X/na6000Isup2.hkl |
CCDC reference: 155857
All H atoms were included in the refinement, at calculated positions, as riding models with C—H set to 0.95 Å (Ar—H), except for the amine H atoms which were located on difference syntheses and both positional and displacement parameters refined.
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.
C32H22Cl4N6S4 | F(000) = 1552 |
Mr = 760.60 | Dx = 1.487 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 28.4777 (13) Å | Cell parameters from 12187 reflections |
b = 8.6020 (3) Å | θ = 1.0–30.5° |
c = 14.2055 (5) Å | µ = 0.63 mm−1 |
β = 102.5620 (13)° | T = 150 K |
V = 3396.5 (2) Å3 | Prism, colourless |
Z = 4 | 0.15 × 0.15 × 0.10 mm |
Enraf Nonius KappaCCD area-detector diffractometer | 7363 independent reflections |
Radiation source: Enraf Nonius FR591 rotating anode | 4286 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.080 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 1.5° |
ϕ and ω scans | h = −36→37 |
Absorption correction: multi-scan SORTAV (Blessing, 1995) | k = −11→10 |
Tmin = 0.912, Tmax = 0.940 | l = −18→17 |
20121 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.148 | w = 1/[σ2(Fo2) + (0.0703P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max < 0.001 |
7363 reflections | Δρmax = 0.33 e Å−3 |
432 parameters | Δρmin = −0.39 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0046 (6) |
C32H22Cl4N6S4 | V = 3396.5 (2) Å3 |
Mr = 760.60 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 28.4777 (13) Å | µ = 0.63 mm−1 |
b = 8.6020 (3) Å | T = 150 K |
c = 14.2055 (5) Å | 0.15 × 0.15 × 0.10 mm |
β = 102.5620 (13)° |
Enraf Nonius KappaCCD area-detector diffractometer | 7363 independent reflections |
Absorption correction: multi-scan SORTAV (Blessing, 1995) | 4286 reflections with I > 2σ(I) |
Tmin = 0.912, Tmax = 0.940 | Rint = 0.080 |
20121 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.148 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | Δρmax = 0.33 e Å−3 |
7363 reflections | Δρmin = −0.39 e Å−3 |
432 parameters |
Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. |
Geometry. Mean plane data ex SHELXL97 ########################### Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 1.3912 (0.0419) x + 8.5813 (0.0009) y - 0.5311 (0.0191) z = 0.7704 (0.0146) * -0.0018 (0.0022) C8A * 0.0025 (0.0024) C9A * -0.0004 (0.0025) C10A * -0.0026 (0.0025) C11A * 0.0033 (0.0025) C12A * -0.0011 (0.0023) C13A Rms deviation of fitted atoms = 0.0022 26.4157 (0.0128) x - 0.5748 (0.0101) y - 7.9624 (0.0140) z = 7.1447 (0.0154) Angle to previous plane (with approximate e.s.d.) = 84.61 (0.11) * -0.0017 (0.0019) N1A * -0.0013 (0.0021) C2A * 0.0036 (0.0020) N3A * -0.0031 (0.0021) C4A * 0.0002 (0.0021) C5A * 0.0023 (0.0020) C6A Rms deviation of fitted atoms = 0.0023 - 2.0118 (0.0420) x + 8.3084 (0.0032) y - 3.2374 (0.0205) z = 4.2869 (0.0157) Angle to previous plane (with approximate e.s.d.) = 87.80 (0.11) * 0.0010 (0.0023) C15A * 0.0009 (0.0025) C16A * -0.0040 (0.0026) C17A * 0.0052 (0.0027) C18A * -0.0032 (0.0025) C19A * 0.0001 (0.0023) C20A Rms deviation of fitted atoms = 0.0030 6.0898 (0.0397) x + 8.3974 (0.0027) y - 1.1546 (0.0187) z = 5.4068 (0.0123) Angle to previous plane (with approximate e.s.d.) = 20.50 (0.07) * -0.0117 (0.0021) C8B * 0.0024 (0.0022) C9B * 0.0091 (0.0024) C10B * -0.0113 (0.0025) C11B * 0.0017 (0.0024) C12B * 0.0098 (0.0023) C13B Rms deviation of fitted atoms = 0.0087 - 26.2289 (0.0129) x + 0.9118 (0.0099) y + 8.0422 (0.0137) z = 3.1829 (0.0112) Angle to previous plane (with approximate e.s.d.) = 83.87 (0.10) * -0.0036 (0.0019) N1B * 0.0057 (0.0020) C2B * -0.0006 (0.0019) N3B * -0.0061 (0.0020) C4B * 0.0076 (0.0020) C5B * -0.0030 (0.0020) C6B Rms deviation of fitted atoms = 0.0050 10.0127 (0.0400) x + 7.9553 (0.0047) y + 0.9270 (0.0200) z = 11.5050 (0.0120) Angle to previous plane (with approximate e.s.d.) = 80.13 (0.10) * -0.0087 (0.0022) C15B * 0.0038 (0.0024) C16B * -0.0002 (0.0026) C17B * 0.0014 (0.0026) C18B * -0.0063 (0.0026) C19B * 0.0100 (0.0025) C20B Rms deviation of fitted atoms = 0.0062 |
x | y | z | Uiso*/Ueq | ||
N1A | 0.47036 (9) | 0.6658 (3) | 0.61528 (16) | 0.0261 (6) | |
C2A | 0.48381 (11) | 0.5371 (3) | 0.66914 (19) | 0.0258 (7) | |
N21A | 0.51080 (11) | 0.5590 (4) | 0.75831 (19) | 0.0342 (7) | |
H21A | 0.5147 (12) | 0.644 (4) | 0.780 (2) | 0.043 (12)* | |
H22A | 0.5146 (14) | 0.483 (5) | 0.793 (3) | 0.062 (14)* | |
N3A | 0.47261 (9) | 0.3895 (3) | 0.64203 (16) | 0.0286 (6) | |
C4A | 0.44511 (11) | 0.3712 (3) | 0.55295 (19) | 0.0267 (7) | |
C5A | 0.42929 (11) | 0.4931 (3) | 0.49126 (19) | 0.0257 (7) | |
H5A | 0.4100 | 0.4777 | 0.4284 | 0.032* | |
C6A | 0.44332 (10) | 0.6389 (3) | 0.52701 (19) | 0.0240 (7) | |
S7A | 0.43223 (4) | 0.17497 (9) | 0.52689 (6) | 0.0444 (3) | |
C8A | 0.39055 (12) | 0.1785 (3) | 0.4140 (2) | 0.0312 (8) | |
C9A | 0.34204 (13) | 0.1709 (4) | 0.4101 (2) | 0.0435 (9) | |
H9A | 0.3305 | 0.1732 | 0.4680 | 0.054* | |
C10A | 0.30979 (13) | 0.1599 (4) | 0.3222 (2) | 0.0482 (10) | |
H10A | 0.2762 | 0.1542 | 0.3191 | 0.060* | |
C11A | 0.32744 (13) | 0.1574 (4) | 0.2393 (2) | 0.0371 (8) | |
Cl1A | 0.28745 (4) | 0.13975 (14) | 0.12823 (6) | 0.0620 (3) | |
C12A | 0.37537 (13) | 0.1660 (4) | 0.2418 (2) | 0.0420 (9) | |
H12A | 0.3867 | 0.1650 | 0.1836 | 0.052* | |
C13A | 0.40742 (12) | 0.1761 (4) | 0.3299 (2) | 0.0387 (8) | |
H13A | 0.4410 | 0.1814 | 0.3326 | 0.048* | |
S14A | 0.42727 (3) | 0.81190 (9) | 0.46199 (5) | 0.0345 (2) | |
C15A | 0.38524 (11) | 0.7488 (3) | 0.35790 (19) | 0.0283 (7) | |
C16A | 0.33700 (13) | 0.7374 (4) | 0.3585 (2) | 0.0417 (9) | |
H16A | 0.3263 | 0.7577 | 0.4162 | 0.052* | |
C17A | 0.30409 (13) | 0.6964 (4) | 0.2752 (2) | 0.0479 (10) | |
H17A | 0.2709 | 0.6873 | 0.2754 | 0.060* | |
C18A | 0.32027 (13) | 0.6690 (4) | 0.1920 (2) | 0.0417 (9) | |
Cl2A | 0.27902 (4) | 0.62041 (16) | 0.08715 (6) | 0.0754 (4) | |
C19A | 0.36806 (13) | 0.6789 (4) | 0.1905 (2) | 0.0452 (9) | |
H19A | 0.3786 | 0.6581 | 0.1328 | 0.057* | |
C20A | 0.40071 (12) | 0.7196 (4) | 0.2736 (2) | 0.0365 (8) | |
H20A | 0.4339 | 0.7277 | 0.2730 | 0.046* | |
N1B | 0.03378 (9) | 1.1381 (3) | 0.37647 (16) | 0.0262 (6) | |
C2B | 0.01437 (10) | 1.0095 (3) | 0.32893 (19) | 0.0247 (7) | |
N21B | −0.01250 (10) | 1.0303 (4) | 0.23939 (18) | 0.0329 (7) | |
H21B | −0.0137 (11) | 1.117 (4) | 0.215 (2) | 0.024 (9)* | |
H22B | −0.0223 (12) | 0.951 (4) | 0.204 (2) | 0.045 (11)* | |
N3B | 0.01966 (9) | 0.8625 (3) | 0.36203 (15) | 0.0252 (6) | |
C4B | 0.04671 (11) | 0.8455 (3) | 0.45152 (19) | 0.0244 (7) | |
C5B | 0.06778 (10) | 0.9680 (3) | 0.50803 (19) | 0.0246 (7) | |
H5B | 0.0862 | 0.9538 | 0.5717 | 0.031* | |
C6B | 0.06011 (10) | 1.1132 (3) | 0.46523 (19) | 0.0236 (7) | |
S7B | 0.05197 (3) | 0.65027 (9) | 0.48769 (5) | 0.0347 (2) | |
C8B | 0.09758 (11) | 0.6535 (3) | 0.59522 (19) | 0.0270 (7) | |
C9B | 0.08499 (12) | 0.6764 (4) | 0.6830 (2) | 0.0341 (8) | |
H9B | 0.0527 | 0.7008 | 0.6853 | 0.043* | |
C10B | 0.11985 (12) | 0.6636 (4) | 0.7677 (2) | 0.0394 (9) | |
H10B | 0.1117 | 0.6800 | 0.8283 | 0.049* | |
C11B | 0.16589 (12) | 0.6271 (4) | 0.7630 (2) | 0.0393 (9) | |
Cl1B | 0.20838 (4) | 0.60209 (15) | 0.87035 (6) | 0.0688 (4) | |
C12B | 0.17931 (12) | 0.6070 (4) | 0.6764 (2) | 0.0415 (9) | |
H12B | 0.2117 | 0.5837 | 0.6747 | 0.052* | |
C13B | 0.14481 (12) | 0.6214 (4) | 0.5921 (2) | 0.0357 (8) | |
H13B | 0.1535 | 0.6092 | 0.5317 | 0.045* | |
S14B | 0.08396 (3) | 1.28593 (9) | 0.52263 (5) | 0.0315 (2) | |
C15B | 0.12233 (11) | 1.2177 (3) | 0.63009 (19) | 0.0271 (7) | |
C16B | 0.10738 (12) | 1.2281 (4) | 0.7163 (2) | 0.0368 (8) | |
H16B | 0.0764 | 1.2684 | 0.7172 | 0.046* | |
C17B | 0.13721 (13) | 1.1802 (4) | 0.8005 (2) | 0.0444 (9) | |
H17B | 0.1268 | 1.1859 | 0.8596 | 0.055* | |
C18B | 0.18226 (13) | 1.1239 (4) | 0.7992 (2) | 0.0410 (9) | |
Cl2B | 0.21979 (4) | 1.06277 (15) | 0.90598 (6) | 0.0721 (4) | |
C19B | 0.19785 (13) | 1.1132 (4) | 0.7142 (2) | 0.0472 (10) | |
H19B | 0.2288 | 1.0722 | 0.7137 | 0.059* | |
C20B | 0.16784 (12) | 1.1628 (4) | 0.6297 (2) | 0.0404 (9) | |
H20B | 0.1786 | 1.1592 | 0.5709 | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0308 (15) | 0.0210 (13) | 0.0240 (12) | 0.0006 (11) | 0.0003 (11) | −0.0016 (11) |
C2A | 0.0291 (18) | 0.0262 (17) | 0.0202 (15) | 0.0014 (14) | 0.0016 (13) | −0.0011 (13) |
N21A | 0.046 (2) | 0.0242 (17) | 0.0257 (15) | −0.0005 (14) | −0.0070 (12) | −0.0054 (14) |
N3A | 0.0373 (17) | 0.0226 (14) | 0.0227 (13) | −0.0013 (12) | −0.0003 (11) | −0.0012 (11) |
C4A | 0.0329 (19) | 0.0250 (17) | 0.0200 (14) | −0.0004 (14) | 0.0010 (13) | −0.0021 (13) |
C5A | 0.0330 (18) | 0.0194 (16) | 0.0212 (14) | −0.0006 (14) | −0.0021 (12) | −0.0010 (12) |
C6A | 0.0261 (17) | 0.0224 (16) | 0.0228 (15) | 0.0001 (13) | 0.0035 (12) | −0.0006 (13) |
S7A | 0.0715 (7) | 0.0186 (4) | 0.0304 (4) | −0.0050 (4) | −0.0165 (4) | 0.0014 (3) |
C8A | 0.047 (2) | 0.0161 (15) | 0.0245 (16) | −0.0027 (14) | −0.0040 (14) | 0.0004 (13) |
C9A | 0.052 (3) | 0.049 (2) | 0.0297 (18) | −0.0034 (19) | 0.0093 (16) | −0.0045 (16) |
C10A | 0.035 (2) | 0.068 (3) | 0.039 (2) | −0.0052 (19) | 0.0033 (16) | 0.0007 (19) |
C11A | 0.043 (2) | 0.038 (2) | 0.0265 (16) | −0.0054 (17) | −0.0012 (15) | −0.0021 (15) |
Cl1A | 0.0496 (6) | 0.0947 (9) | 0.0329 (5) | −0.0096 (6) | −0.0103 (4) | −0.0044 (5) |
C12A | 0.039 (2) | 0.061 (2) | 0.0259 (17) | −0.0015 (18) | 0.0059 (15) | 0.0006 (17) |
C13A | 0.035 (2) | 0.044 (2) | 0.0345 (18) | −0.0056 (16) | 0.0016 (15) | 0.0029 (16) |
S14A | 0.0505 (6) | 0.0179 (4) | 0.0285 (4) | 0.0005 (4) | −0.0057 (4) | −0.0001 (3) |
C15A | 0.038 (2) | 0.0180 (16) | 0.0250 (15) | 0.0035 (14) | −0.0014 (13) | 0.0007 (13) |
C16A | 0.045 (2) | 0.050 (2) | 0.0295 (17) | 0.0074 (18) | 0.0063 (15) | −0.0075 (16) |
C17A | 0.031 (2) | 0.073 (3) | 0.0369 (19) | −0.0007 (19) | 0.0025 (16) | −0.0074 (19) |
C18A | 0.041 (2) | 0.053 (2) | 0.0270 (17) | −0.0079 (18) | −0.0033 (15) | 0.0001 (16) |
Cl2A | 0.0587 (7) | 0.1283 (11) | 0.0317 (5) | −0.0276 (7) | −0.0066 (5) | −0.0079 (6) |
C19A | 0.049 (2) | 0.059 (2) | 0.0282 (17) | −0.0121 (19) | 0.0084 (16) | −0.0060 (17) |
C20A | 0.033 (2) | 0.042 (2) | 0.0325 (18) | −0.0054 (16) | 0.0041 (15) | −0.0023 (15) |
N1B | 0.0310 (15) | 0.0214 (14) | 0.0246 (13) | −0.0002 (11) | 0.0028 (11) | 0.0003 (11) |
C2B | 0.0274 (18) | 0.0256 (17) | 0.0202 (14) | 0.0026 (14) | 0.0031 (12) | 0.0014 (13) |
N21B | 0.0448 (19) | 0.0252 (16) | 0.0234 (14) | −0.0018 (14) | −0.0043 (12) | 0.0030 (14) |
N3B | 0.0299 (15) | 0.0224 (14) | 0.0216 (12) | 0.0025 (11) | 0.0015 (10) | 0.0001 (10) |
C4B | 0.0296 (18) | 0.0229 (16) | 0.0206 (14) | 0.0013 (13) | 0.0048 (12) | 0.0035 (12) |
C5B | 0.0319 (18) | 0.0211 (16) | 0.0185 (14) | −0.0001 (13) | 0.0004 (12) | −0.0004 (12) |
C6B | 0.0283 (18) | 0.0211 (16) | 0.0213 (14) | 0.0001 (13) | 0.0053 (12) | 0.0020 (12) |
S7B | 0.0512 (6) | 0.0180 (4) | 0.0274 (4) | −0.0013 (4) | −0.0077 (4) | 0.0012 (3) |
C8B | 0.040 (2) | 0.0146 (15) | 0.0225 (15) | −0.0003 (14) | −0.0027 (13) | 0.0003 (12) |
C9B | 0.0317 (19) | 0.038 (2) | 0.0323 (17) | 0.0049 (15) | 0.0051 (14) | 0.0004 (15) |
C10B | 0.039 (2) | 0.053 (2) | 0.0256 (16) | −0.0032 (17) | 0.0073 (15) | 0.0017 (16) |
C11B | 0.035 (2) | 0.048 (2) | 0.0301 (17) | −0.0010 (17) | −0.0027 (15) | 0.0065 (16) |
Cl1B | 0.0476 (7) | 0.1083 (10) | 0.0398 (5) | 0.0003 (6) | −0.0139 (4) | 0.0095 (6) |
C12B | 0.028 (2) | 0.055 (2) | 0.0405 (19) | 0.0004 (17) | 0.0048 (15) | −0.0015 (18) |
C13B | 0.042 (2) | 0.036 (2) | 0.0293 (17) | −0.0004 (16) | 0.0073 (15) | −0.0032 (15) |
S14B | 0.0436 (5) | 0.0179 (4) | 0.0287 (4) | −0.0022 (4) | −0.0018 (3) | 0.0005 (3) |
C15B | 0.0331 (19) | 0.0221 (16) | 0.0241 (15) | −0.0052 (14) | 0.0023 (13) | −0.0046 (13) |
C16B | 0.035 (2) | 0.042 (2) | 0.0330 (18) | 0.0018 (16) | 0.0078 (15) | −0.0026 (16) |
C17B | 0.048 (2) | 0.059 (2) | 0.0257 (17) | −0.0020 (19) | 0.0073 (16) | −0.0041 (17) |
C18B | 0.041 (2) | 0.050 (2) | 0.0274 (17) | −0.0030 (18) | −0.0009 (15) | 0.0042 (16) |
Cl2B | 0.0602 (7) | 0.1112 (10) | 0.0360 (5) | 0.0046 (7) | −0.0095 (5) | 0.0163 (6) |
C19B | 0.040 (2) | 0.067 (3) | 0.0343 (19) | 0.0101 (19) | 0.0057 (16) | 0.0028 (18) |
C20B | 0.043 (2) | 0.053 (2) | 0.0258 (16) | 0.0011 (18) | 0.0098 (15) | 0.0016 (16) |
N1A—C6A | 1.341 (3) | N1B—C6B | 1.337 (3) |
N1A—C2A | 1.353 (3) | N1B—C2B | 1.350 (3) |
C2A—N21A | 1.344 (4) | C2B—N3B | 1.346 (4) |
C2A—N3A | 1.345 (4) | C2B—N21B | 1.346 (3) |
N21A—H21A | 0.79 (4) | N21B—H21B | 0.82 (3) |
N21A—H22A | 0.81 (4) | N21B—H22B | 0.86 (3) |
N3A—C4A | 1.345 (3) | N3B—C4B | 1.343 (3) |
C4A—C5A | 1.378 (4) | C4B—C5B | 1.380 (4) |
C4A—S7A | 1.750 (3) | C4B—S7B | 1.753 (3) |
C5A—C6A | 1.380 (4) | C5B—C6B | 1.385 (4) |
C5A—H5A | 0.9500 | C5B—H5B | 0.9500 |
C6A—S14A | 1.758 (3) | C6B—S14B | 1.759 (3) |
S7A—C8A | 1.776 (3) | S7B—C8B | 1.777 (3) |
C8A—C9A | 1.372 (5) | C8B—C9B | 1.385 (4) |
C8A—C13A | 1.382 (4) | C8B—C13B | 1.383 (4) |
C9A—C10A | 1.383 (4) | C9B—C10B | 1.387 (4) |
C9A—H9A | 0.9500 | C9B—H9B | 0.9500 |
C10A—C11A | 1.378 (4) | C10B—C11B | 1.364 (5) |
C10A—H10A | 0.9500 | C10B—H10B | 0.9500 |
C11A—C12A | 1.360 (5) | C11B—C12B | 1.375 (4) |
C11A—Cl1A | 1.740 (3) | C11B—Cl1B | 1.742 (3) |
C12A—C13A | 1.382 (4) | C12B—C13B | 1.379 (4) |
C12A—H12A | 0.9500 | C12B—H12B | 0.9500 |
C13A—H13A | 0.9500 | C13B—H13B | 0.9500 |
S14A—C15A | 1.773 (3) | S14B—C15B | 1.773 (3) |
C15A—C16A | 1.379 (4) | C15B—C20B | 1.381 (4) |
C15A—C20A | 1.386 (4) | C15B—C16B | 1.385 (4) |
C16A—C17A | 1.386 (4) | C16B—C17B | 1.371 (4) |
C16A—H16A | 0.9500 | C16B—H16B | 0.9500 |
C17A—C18A | 1.379 (5) | C17B—C18B | 1.375 (5) |
C17A—H17A | 0.9500 | C17B—H17B | 0.9500 |
C18A—C19A | 1.369 (5) | C18B—C19B | 1.377 (4) |
C18A—Cl2A | 1.735 (3) | C18B—Cl2B | 1.736 (3) |
C19A—C20A | 1.380 (4) | C19B—C20B | 1.382 (4) |
C19A—H19A | 0.9500 | C19B—H19B | 0.9500 |
C20A—H20A | 0.9500 | C20B—H20B | 0.9500 |
C6A—N1A—C2A | 115.0 (2) | C6B—N1B—C2B | 115.2 (2) |
N21A—C2A—N3A | 117.0 (3) | N3B—C2B—N21B | 116.9 (3) |
N21A—C2A—N1A | 116.8 (3) | N3B—C2B—N1B | 126.3 (2) |
N3A—C2A—N1A | 126.2 (2) | N21B—C2B—N1B | 116.8 (3) |
C2A—N21A—H21A | 120 (2) | C2B—N21B—H21B | 119 (2) |
C2A—N21A—H22A | 116 (3) | C2B—N21B—H22B | 120 (2) |
H21A—N21A—H22A | 121 (4) | H21B—N21B—H22B | 119 (3) |
C4A—N3A—C2A | 115.7 (2) | C4B—N3B—C2B | 115.5 (2) |
N3A—C4A—C5A | 123.5 (3) | N3B—C4B—C5B | 123.7 (3) |
N3A—C4A—S7A | 111.4 (2) | N3B—C4B—S7B | 112.1 (2) |
C5A—C4A—S7A | 125.1 (2) | C5B—C4B—S7B | 124.2 (2) |
C4A—C5A—C6A | 115.4 (2) | C4B—C5B—C6B | 115.2 (2) |
C4A—C5A—H5A | 122.3 | C4B—C5B—H5B | 122.4 |
C6A—C5A—H5A | 122.3 | C6B—C5B—H5B | 122.4 |
N1A—C6A—C5A | 124.2 (3) | N1B—C6B—C5B | 124.1 (3) |
N1A—C6A—S14A | 112.1 (2) | N1B—C6B—S14B | 112.5 (2) |
C5A—C6A—S14A | 123.7 (2) | C5B—C6B—S14B | 123.4 (2) |
C4A—S7A—C8A | 104.04 (13) | C4B—S7B—C8B | 103.69 (13) |
C9A—C8A—C13A | 120.0 (3) | C9B—C8B—C13B | 120.1 (3) |
C9A—C8A—S7A | 120.4 (2) | C9B—C8B—S7B | 119.5 (3) |
C13A—C8A—S7A | 119.4 (3) | C13B—C8B—S7B | 120.2 (2) |
C8A—C9A—C10A | 120.3 (3) | C8B—C9B—C10B | 119.5 (3) |
C8A—C9A—H9A | 119.8 | C8B—C9B—H9B | 120.2 |
C10A—C9A—H9A | 119.8 | C10B—C9B—H9B | 120.2 |
C11A—C10A—C9A | 118.6 (3) | C11B—C10B—C9B | 119.4 (3) |
C11A—C10A—H10A | 120.7 | C11B—C10B—H10B | 120.3 |
C9A—C10A—H10A | 120.7 | C9B—C10B—H10B | 120.3 |
C12A—C11A—C10A | 121.9 (3) | C10B—C11B—C12B | 122.0 (3) |
C12A—C11A—Cl1A | 118.9 (2) | C10B—C11B—Cl1B | 118.5 (3) |
C10A—C11A—Cl1A | 119.2 (3) | C12B—C11B—Cl1B | 119.5 (3) |
C11A—C12A—C13A | 119.2 (3) | C11B—C12B—C13B | 118.7 (3) |
C11A—C12A—H12A | 120.4 | C11B—C12B—H12B | 120.6 |
C13A—C12A—H12A | 120.4 | C13B—C12B—H12B | 120.6 |
C12A—C13A—C8A | 119.9 (3) | C12B—C13B—C8B | 120.3 (3) |
C12A—C13A—H13A | 120.0 | C12B—C13B—H13B | 119.9 |
C8A—C13A—H13A | 120.0 | C8B—C13B—H13B | 119.9 |
C6A—S14A—C15A | 103.32 (13) | C6B—S14B—C15B | 102.90 (13) |
C16A—C15A—C20A | 119.8 (3) | C20B—C15B—C16B | 119.7 (3) |
C16A—C15A—S14A | 120.6 (2) | C20B—C15B—S14B | 120.8 (2) |
C20A—C15A—S14A | 119.5 (3) | C16B—C15B—S14B | 119.4 (2) |
C15A—C16A—C17A | 120.1 (3) | C17B—C16B—C15B | 120.1 (3) |
C15A—C16A—H16A | 119.9 | C17B—C16B—H16B | 120.0 |
C17A—C16A—H16A | 119.9 | C15B—C16B—H16B | 120.0 |
C18A—C17A—C16A | 119.0 (3) | C16B—C17B—C18B | 119.8 (3) |
C18A—C17A—H17A | 120.5 | C16B—C17B—H17B | 120.1 |
C16A—C17A—H17A | 120.5 | C18B—C17B—H17B | 120.1 |
C19A—C18A—C17A | 121.4 (3) | C19B—C18B—C17B | 121.0 (3) |
C19A—C18A—Cl2A | 119.4 (3) | C19B—C18B—Cl2B | 119.4 (3) |
C17A—C18A—Cl2A | 119.1 (3) | C17B—C18B—Cl2B | 119.6 (3) |
C18A—C19A—C20A | 119.3 (3) | C18B—C19B—C20B | 119.0 (3) |
C18A—C19A—H19A | 120.3 | C18B—C19B—H19B | 120.5 |
C20A—C19A—H19A | 120.3 | C20B—C19B—H19B | 120.5 |
C19A—C20A—C15A | 120.2 (3) | C15B—C20B—C19B | 120.4 (3) |
C19A—C20A—H20A | 119.9 | C15B—C20B—H20B | 119.8 |
C15A—C20A—H20A | 119.9 | C19B—C20B—H20B | 119.8 |
C6A—N1A—C2A—N21A | −179.7 (3) | C6B—N1B—C2B—N3B | −0.8 (4) |
C6A—N1A—C2A—N3A | 0.0 (4) | C6B—N1B—C2B—N21B | 179.8 (3) |
N21A—C2A—N3A—C4A | 179.2 (3) | N21B—C2B—N3B—C4B | 179.9 (3) |
N1A—C2A—N3A—C4A | −0.5 (5) | N1B—C2B—N3B—C4B | 0.6 (4) |
C2A—N3A—C4A—C5A | 0.7 (4) | C2B—N3B—C4B—C5B | 0.7 (4) |
C2A—N3A—C4A—S7A | −179.1 (2) | C2B—N3B—C4B—S7B | −179.4 (2) |
N3A—C4A—C5A—C6A | −0.4 (5) | N3B—C4B—C5B—C6B | −1.4 (4) |
S7A—C4A—C5A—C6A | 179.3 (2) | S7B—C4B—C5B—C6B | 178.7 (2) |
C2A—N1A—C6A—C5A | 0.3 (4) | C2B—N1B—C6B—C5B | −0.1 (4) |
C2A—N1A—C6A—S14A | 179.8 (2) | C2B—N1B—C6B—S14B | −179.8 (2) |
C4A—C5A—C6A—N1A | −0.2 (5) | C4B—C5B—C6B—N1B | 1.1 (4) |
C4A—C5A—C6A—S14A | −179.6 (2) | C4B—C5B—C6B—S14B | −179.2 (2) |
N3A—C4A—S7A—C8A | 173.4 (2) | N3B—C4B—S7B—C8B | 169.2 (2) |
C5A—C4A—S7A—C8A | −6.4 (3) | C5B—C4B—S7B—C8B | −10.9 (3) |
C4A—S7A—C8A—C9A | −96.5 (3) | C4B—S7B—C8B—C9B | 89.3 (3) |
C4A—S7A—C8A—C13A | 88.8 (3) | C4B—S7B—C8B—C13B | −95.8 (3) |
C13A—C8A—C9A—C10A | 0.4 (5) | C13B—C8B—C9B—C10B | −1.4 (5) |
S7A—C8A—C9A—C10A | −174.3 (3) | S7B—C8B—C9B—C10B | 173.6 (2) |
C8A—C9A—C10A—C11A | −0.2 (5) | C8B—C9B—C10B—C11B | −0.6 (5) |
C9A—C10A—C11A—C12A | −0.3 (5) | C9B—C10B—C11B—C12B | 2.0 (5) |
C9A—C10A—C11A—Cl1A | 178.8 (3) | C9B—C10B—C11B—Cl1B | −176.8 (3) |
C10A—C11A—C12A—C13A | 0.6 (5) | C10B—C11B—C12B—C13B | −1.3 (5) |
Cl1A—C11A—C12A—C13A | −178.4 (3) | Cl1B—C11B—C12B—C13B | 177.5 (3) |
C11A—C12A—C13A—C8A | −0.5 (5) | C11B—C12B—C13B—C8B | −0.8 (5) |
C9A—C8A—C13A—C12A | 0.0 (5) | C9B—C8B—C13B—C12B | 2.1 (5) |
S7A—C8A—C13A—C12A | 174.7 (3) | S7B—C8B—C13B—C12B | −172.8 (2) |
N1A—C6A—S14A—C15A | −171.6 (2) | N1B—C6B—S14B—C15B | −173.1 (2) |
C5A—C6A—S14A—C15A | 7.9 (3) | C5B—C6B—S14B—C15B | 7.1 (3) |
C6A—S14A—C15A—C16A | 87.6 (3) | C6B—S14B—C15B—C20B | 80.6 (3) |
C6A—S14A—C15A—C20A | −96.2 (3) | C6B—S14B—C15B—C16B | −103.1 (3) |
C20A—C15A—C16A—C17A | 0.2 (5) | C20B—C15B—C16B—C17B | −1.7 (5) |
S14A—C15A—C16A—C17A | 176.4 (3) | S14B—C15B—C16B—C17B | −178.0 (3) |
C15A—C16A—C17A—C18A | −0.7 (5) | C15B—C16B—C17B—C18B | 0.9 (5) |
C16A—C17A—C18A—C19A | 1.1 (6) | C16B—C17B—C18B—C19B | −0.6 (6) |
C16A—C17A—C18A—Cl2A | −179.0 (3) | C16B—C17B—C18B—Cl2B | −179.8 (3) |
C17A—C18A—C19A—C20A | −1.0 (6) | C17B—C18B—C19B—C20B | 1.2 (6) |
Cl2A—C18A—C19A—C20A | 179.1 (3) | Cl2B—C18B—C19B—C20B | −179.7 (3) |
C18A—C19A—C20A—C15A | 0.5 (5) | C16B—C15B—C20B—C19B | 2.3 (5) |
C16A—C15A—C20A—C19A | −0.1 (5) | S14B—C15B—C20B—C19B | 178.6 (3) |
S14A—C15A—C20A—C19A | −176.4 (3) | C18B—C19B—C20B—C15B | −2.0 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21A—H21A···N3Ai | 0.79 (4) | 2.38 (4) | 3.165 (4) | 175 (3) |
N21A—H21A···S7Ai | 0.79 (4) | 2.84 (3) | 3.284 (3) | 118 (3) |
N21B—H21B···N3Bii | 0.82 (3) | 2.37 (3) | 3.187 (4) | 178 (3) |
N21B—H21B···S7Bii | 0.82 (3) | 2.86 (3) | 3.340 (3) | 120 (2) |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C32H22Cl4N6S4 |
Mr | 760.60 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 150 |
a, b, c (Å) | 28.4777 (13), 8.6020 (3), 14.2055 (5) |
β (°) | 102.5620 (13) |
V (Å3) | 3396.5 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.63 |
Crystal size (mm) | 0.15 × 0.15 × 0.10 |
Data collection | |
Diffractometer | Enraf Nonius KappaCCD area-detector diffractometer |
Absorption correction | Multi-scan SORTAV (Blessing, 1995) |
Tmin, Tmax | 0.912, 0.940 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20121, 7363, 4286 |
Rint | 0.080 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.148, 0.97 |
No. of reflections | 7363 |
No. of parameters | 432 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.33, −0.39 |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N21A—H21A···N3Ai | 0.79 (4) | 2.38 (4) | 3.165 (4) | 175 (3) |
N21A—H21A···S7Ai | 0.79 (4) | 2.84 (3) | 3.284 (3) | 118 (3) |
N21B—H21B···N3Bii | 0.82 (3) | 2.37 (3) | 3.187 (4) | 178 (3) |
N21B—H21B···S7Bii | 0.82 (3) | 2.86 (3) | 3.340 (3) | 120 (2) |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x, y+1/2, −z+1/2. |
NO COMMENT