Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804024924/ya6215sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804024924/ya6215Isup2.hkl |
CCDC reference: 255882
Data collection: SMART (Bruker, 2002); cell refinement: SHELXTL (Sheldrick, 2001); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C18H24NS2+·Cl− | F(000) = 1504 |
Mr = 353.95 | Dx = 1.269 Mg m−3 |
Orthorhombic, P21212 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2 2ab | Cell parameters from 1007 reflections |
a = 16.396 (4) Å | θ = 3.2–27.8° |
b = 31.633 (8) Å | µ = 0.43 mm−1 |
c = 7.1438 (19) Å | T = 120 K |
V = 3705.1 (17) Å3 | Needle, yellow |
Z = 8 | 0.36 × 0.04 × 0.04 mm |
Bruker SMART APEX diffractometer | 8603 independent reflections |
Radiation source: fine-focus sealed tube | 8297 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 836.6 pixels mm-1 | θmax = 28.3°, θmin = 1.8° |
ω scans | h = −20→21 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | k = −40→41 |
Tmin = 0.861, Tmax = 0.983 | l = −9→9 |
41652 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)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.0831P)2 + 1.3761P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
8603 reflections | Δρmax = 0.50 e Å−3 |
400 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 3633 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.55 (6) |
Experimental. Data collection is performed with four batch runs at φ = 0.00 ° (600 frames), at φ = 90.00 ° (600 frames), at φ = 180 ° (600 frames) and at φ = 270 ° (600 frames). Frame width = 0.30 \& in ω. Data is merged, corrected for decay, and treated with multi-scan absorption corrections. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.91050 (4) | 0.448773 (18) | 0.52541 (9) | 0.02306 (14) | |
Cl2 | 0.08552 (3) | 0.440842 (18) | 1.02930 (9) | 0.02197 (13) | |
N1 | 0.89336 (12) | 0.46171 (6) | 0.0836 (3) | 0.0225 (4) | |
H1B | 0.9084 | 0.4884 | 0.0514 | 0.034* | |
H1C | 0.9231 | 0.4428 | 0.0164 | 0.034* | |
H1D | 0.9025 | 0.4577 | 0.2079 | 0.034* | |
N2 | 0.10306 (12) | 0.45370 (7) | 0.5858 (3) | 0.0230 (4) | |
H2B | 0.0881 | 0.4804 | 0.5538 | 0.034* | |
H2C | 0.0939 | 0.4496 | 0.7102 | 0.034* | |
H2D | 0.0732 | 0.4348 | 0.5186 | 0.034* | |
S1 | 0.88438 (4) | 0.36459 (2) | −0.04757 (9) | 0.02450 (14) | |
S2 | 0.64440 (4) | 0.46346 (2) | 0.32759 (11) | 0.02734 (16) | |
S3 | 0.35138 (4) | 0.45585 (2) | 0.82493 (11) | 0.02917 (17) | |
S4 | 0.10950 (5) | 0.35472 (2) | 0.47148 (9) | 0.02860 (16) | |
C1 | 0.87375 (14) | 0.32030 (8) | 0.4552 (4) | 0.0222 (5) | |
H1A | 0.8736 | 0.3475 | 0.5115 | 0.027* | |
C2 | 0.84365 (16) | 0.28587 (9) | 0.5544 (4) | 0.0270 (5) | |
H2A | 0.8236 | 0.2897 | 0.6780 | 0.032* | |
C3 | 0.84272 (17) | 0.24640 (9) | 0.4744 (4) | 0.0306 (6) | |
H3A | 0.8215 | 0.2230 | 0.5416 | 0.037* | |
C4 | 0.8730 (2) | 0.24100 (9) | 0.2947 (4) | 0.0337 (7) | |
H4A | 0.8724 | 0.2137 | 0.2390 | 0.040* | |
C5 | 0.90426 (18) | 0.27505 (8) | 0.1954 (4) | 0.0283 (6) | |
H5A | 0.9258 | 0.2709 | 0.0733 | 0.034* | |
C6 | 0.90402 (15) | 0.31544 (8) | 0.2752 (4) | 0.0199 (5) | |
C7 | 0.93728 (16) | 0.35285 (8) | 0.1707 (4) | 0.0234 (5) | |
H7A | 0.9955 | 0.3476 | 0.1426 | 0.028* | |
H7B | 0.9343 | 0.3780 | 0.2528 | 0.028* | |
C8 | 0.67372 (15) | 0.36401 (8) | 0.5734 (3) | 0.0204 (5) | |
H8A | 0.7233 | 0.3624 | 0.5048 | 0.025* | |
C9 | 0.63650 (17) | 0.32728 (9) | 0.6322 (4) | 0.0250 (5) | |
H9A | 0.6601 | 0.3007 | 0.6032 | 0.030* | |
C10 | 0.56450 (17) | 0.32921 (9) | 0.7340 (4) | 0.0300 (6) | |
H10A | 0.5390 | 0.3040 | 0.7761 | 0.036* | |
C11 | 0.53010 (16) | 0.36805 (10) | 0.7736 (4) | 0.0272 (6) | |
H11A | 0.4806 | 0.3694 | 0.8424 | 0.033* | |
C12 | 0.56711 (15) | 0.40491 (9) | 0.7139 (4) | 0.0237 (5) | |
H12A | 0.5428 | 0.4314 | 0.7417 | 0.028* | |
C13 | 0.64002 (15) | 0.40338 (8) | 0.6128 (3) | 0.0192 (5) | |
C14 | 0.68167 (15) | 0.44312 (8) | 0.5504 (4) | 0.0249 (5) | |
H14A | 0.7409 | 0.4376 | 0.5394 | 0.030* | |
H14B | 0.6740 | 0.4651 | 0.6476 | 0.030* | |
C15 | 0.78168 (15) | 0.37539 (8) | 0.0342 (4) | 0.0210 (5) | |
H15A | 0.7448 | 0.3755 | −0.0755 | 0.025* | |
H15B | 0.7645 | 0.3518 | 0.1165 | 0.025* | |
C16 | 0.67683 (15) | 0.42253 (8) | 0.1673 (4) | 0.0233 (5) | |
H16A | 0.6541 | 0.3953 | 0.2112 | 0.028* | |
H16B | 0.6525 | 0.4285 | 0.0433 | 0.028* | |
C17 | 0.76945 (15) | 0.41703 (8) | 0.1412 (4) | 0.0190 (5) | |
H17A | 0.7954 | 0.4143 | 0.2674 | 0.023* | |
C18 | 0.80510 (14) | 0.45564 (8) | 0.0428 (4) | 0.0221 (5) | |
H18A | 0.7976 | 0.4525 | −0.0940 | 0.027* | |
H18B | 0.7748 | 0.4811 | 0.0829 | 0.027* | |
C19 | 0.43584 (15) | 0.40176 (8) | 1.2149 (4) | 0.0225 (5) | |
H19A | 0.4564 | 0.4292 | 1.2411 | 0.027* | |
C20 | 0.47821 (16) | 0.36663 (10) | 1.2771 (4) | 0.0293 (6) | |
H20A | 0.5269 | 0.3701 | 1.3475 | 0.035* | |
C21 | 0.44989 (17) | 0.32639 (10) | 1.2371 (4) | 0.0295 (6) | |
H21A | 0.4794 | 0.3023 | 1.2786 | 0.035* | |
C22 | 0.37838 (18) | 0.32148 (9) | 1.1365 (4) | 0.0272 (6) | |
H22A | 0.3586 | 0.2939 | 1.1089 | 0.033* | |
C23 | 0.33533 (15) | 0.35683 (8) | 1.0756 (3) | 0.0201 (5) | |
H23A | 0.2862 | 0.3532 | 1.0069 | 0.024* | |
C24 | 0.36342 (15) | 0.39745 (8) | 1.1142 (3) | 0.0188 (5) | |
C25 | 0.31687 (16) | 0.43547 (8) | 1.0507 (4) | 0.0251 (5) | |
H25A | 0.3224 | 0.4580 | 1.1460 | 0.030* | |
H25B | 0.2583 | 0.4281 | 1.0414 | 0.030* | |
C26 | 0.13763 (15) | 0.31087 (8) | 0.9772 (4) | 0.0233 (5) | |
H26A | 0.1325 | 0.3376 | 1.0369 | 0.028* | |
C27 | 0.17436 (16) | 0.27758 (9) | 1.0724 (4) | 0.0269 (6) | |
H27A | 0.1932 | 0.2814 | 1.1970 | 0.032* | |
C28 | 0.18329 (18) | 0.23893 (9) | 0.9853 (4) | 0.0291 (6) | |
H28A | 0.2095 | 0.2163 | 1.0486 | 0.035* | |
C29 | 0.1538 (2) | 0.23324 (9) | 0.8039 (4) | 0.0352 (7) | |
H29A | 0.1595 | 0.2066 | 0.7441 | 0.042* | |
C30 | 0.11637 (18) | 0.26619 (8) | 0.7111 (4) | 0.0291 (6) | |
H30A | 0.0959 | 0.2619 | 0.5881 | 0.035* | |
C31 | 0.10829 (15) | 0.30573 (8) | 0.7961 (4) | 0.0220 (5) | |
C32 | 0.06632 (15) | 0.34166 (8) | 0.6998 (4) | 0.0240 (5) | |
H32A | 0.0693 | 0.3670 | 0.7811 | 0.029* | |
H32B | 0.0080 | 0.3344 | 0.6836 | 0.029* | |
C33 | 0.31999 (15) | 0.41423 (9) | 0.6660 (4) | 0.0245 (5) | |
H33A | 0.3441 | 0.4200 | 0.5416 | 0.029* | |
H33B | 0.3432 | 0.3872 | 0.7112 | 0.029* | |
C34 | 0.21346 (16) | 0.36724 (8) | 0.5329 (4) | 0.0257 (5) | |
H34A | 0.2354 | 0.3436 | 0.6086 | 0.031* | |
H34B | 0.2458 | 0.3685 | 0.4160 | 0.031* | |
C35 | 0.22768 (15) | 0.40845 (8) | 0.6414 (3) | 0.0187 (5) | |
H35A | 0.2023 | 0.4056 | 0.7681 | 0.022* | |
C36 | 0.19134 (15) | 0.44757 (8) | 0.5449 (4) | 0.0241 (5) | |
H36A | 0.2217 | 0.4730 | 0.5863 | 0.029* | |
H36B | 0.1987 | 0.4448 | 0.4080 | 0.029* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0204 (3) | 0.0199 (3) | 0.0289 (3) | −0.0006 (2) | −0.0028 (2) | −0.0028 (2) |
Cl2 | 0.0196 (3) | 0.0176 (3) | 0.0287 (3) | −0.0001 (2) | 0.0035 (2) | −0.0018 (2) |
N1 | 0.0193 (10) | 0.0168 (10) | 0.0314 (11) | −0.0022 (8) | 0.0037 (9) | 0.0044 (9) |
N2 | 0.0189 (10) | 0.0197 (10) | 0.0303 (11) | 0.0016 (8) | −0.0014 (9) | 0.0032 (9) |
S1 | 0.0349 (3) | 0.0227 (3) | 0.0160 (3) | −0.0001 (2) | 0.0046 (3) | −0.0024 (2) |
S2 | 0.0215 (3) | 0.0225 (3) | 0.0380 (4) | 0.0023 (2) | 0.0050 (3) | 0.0065 (3) |
S3 | 0.0223 (3) | 0.0232 (3) | 0.0419 (4) | −0.0007 (3) | −0.0021 (3) | 0.0107 (3) |
S4 | 0.0414 (4) | 0.0253 (3) | 0.0191 (3) | 0.0055 (3) | −0.0088 (3) | −0.0041 (2) |
C1 | 0.0178 (11) | 0.0242 (12) | 0.0247 (13) | 0.0034 (9) | −0.0040 (10) | −0.0065 (10) |
C2 | 0.0248 (13) | 0.0380 (14) | 0.0183 (12) | 0.0035 (11) | −0.0030 (11) | 0.0000 (11) |
C3 | 0.0337 (14) | 0.0296 (13) | 0.0286 (15) | −0.0003 (11) | −0.0066 (12) | 0.0099 (12) |
C4 | 0.0531 (19) | 0.0189 (12) | 0.0290 (14) | 0.0045 (12) | −0.0025 (14) | −0.0038 (11) |
C5 | 0.0396 (15) | 0.0225 (12) | 0.0229 (12) | 0.0072 (11) | 0.0021 (12) | −0.0043 (10) |
C6 | 0.0163 (10) | 0.0210 (11) | 0.0224 (12) | 0.0047 (9) | −0.0024 (9) | −0.0004 (9) |
C7 | 0.0211 (12) | 0.0253 (12) | 0.0238 (12) | 0.0005 (10) | −0.0002 (10) | 0.0003 (10) |
C8 | 0.0180 (11) | 0.0293 (13) | 0.0139 (10) | 0.0030 (10) | −0.0019 (9) | −0.0008 (10) |
C9 | 0.0272 (13) | 0.0288 (13) | 0.0191 (12) | 0.0046 (11) | −0.0061 (10) | 0.0014 (10) |
C10 | 0.0295 (14) | 0.0345 (15) | 0.0261 (14) | −0.0053 (11) | −0.0040 (11) | 0.0126 (12) |
C11 | 0.0187 (12) | 0.0463 (16) | 0.0166 (12) | 0.0001 (11) | 0.0014 (10) | 0.0057 (11) |
C12 | 0.0195 (12) | 0.0342 (14) | 0.0173 (12) | 0.0043 (10) | −0.0022 (10) | −0.0044 (10) |
C13 | 0.0159 (11) | 0.0255 (12) | 0.0161 (11) | 0.0009 (9) | −0.0032 (9) | −0.0055 (9) |
C14 | 0.0215 (11) | 0.0267 (13) | 0.0265 (13) | −0.0021 (10) | 0.0015 (11) | −0.0088 (11) |
C15 | 0.0229 (11) | 0.0220 (11) | 0.0180 (11) | −0.0045 (9) | −0.0035 (10) | 0.0014 (10) |
C16 | 0.0200 (11) | 0.0280 (13) | 0.0218 (12) | −0.0034 (10) | −0.0015 (10) | 0.0033 (10) |
C17 | 0.0192 (11) | 0.0211 (12) | 0.0167 (11) | −0.0011 (9) | −0.0036 (9) | 0.0021 (9) |
C18 | 0.0207 (11) | 0.0182 (11) | 0.0273 (13) | −0.0020 (9) | −0.0009 (10) | 0.0025 (10) |
C19 | 0.0197 (11) | 0.0268 (13) | 0.0211 (12) | −0.0065 (10) | −0.0016 (10) | −0.0039 (10) |
C20 | 0.0172 (11) | 0.0490 (17) | 0.0216 (13) | −0.0025 (12) | −0.0018 (10) | 0.0074 (12) |
C21 | 0.0278 (13) | 0.0371 (15) | 0.0236 (14) | 0.0062 (12) | 0.0030 (11) | 0.0128 (12) |
C22 | 0.0342 (14) | 0.0257 (13) | 0.0216 (12) | −0.0002 (11) | 0.0049 (11) | 0.0039 (10) |
C23 | 0.0200 (11) | 0.0265 (12) | 0.0138 (10) | −0.0051 (9) | −0.0016 (9) | −0.0005 (9) |
C24 | 0.0177 (11) | 0.0266 (12) | 0.0120 (10) | −0.0012 (9) | 0.0037 (9) | −0.0013 (9) |
C25 | 0.0213 (11) | 0.0244 (12) | 0.0296 (14) | 0.0057 (10) | −0.0004 (11) | −0.0039 (11) |
C26 | 0.0181 (11) | 0.0282 (12) | 0.0237 (13) | −0.0021 (9) | 0.0022 (10) | −0.0078 (10) |
C27 | 0.0264 (13) | 0.0356 (14) | 0.0187 (12) | −0.0035 (11) | −0.0008 (10) | −0.0033 (11) |
C28 | 0.0382 (14) | 0.0257 (13) | 0.0233 (13) | −0.0010 (11) | 0.0052 (12) | 0.0045 (11) |
C29 | 0.0579 (19) | 0.0206 (13) | 0.0271 (14) | −0.0027 (13) | 0.0045 (14) | −0.0039 (11) |
C30 | 0.0430 (16) | 0.0233 (13) | 0.0209 (12) | −0.0031 (12) | −0.0049 (12) | −0.0043 (10) |
C31 | 0.0181 (11) | 0.0217 (12) | 0.0262 (13) | −0.0043 (9) | 0.0028 (10) | −0.0025 (10) |
C32 | 0.0195 (12) | 0.0260 (13) | 0.0265 (13) | 0.0001 (10) | −0.0003 (10) | −0.0069 (11) |
C33 | 0.0208 (12) | 0.0303 (13) | 0.0223 (13) | 0.0049 (10) | 0.0036 (10) | 0.0090 (11) |
C34 | 0.0307 (13) | 0.0248 (12) | 0.0215 (12) | 0.0097 (10) | 0.0073 (11) | 0.0023 (11) |
C35 | 0.0192 (11) | 0.0212 (11) | 0.0157 (11) | 0.0063 (9) | 0.0042 (9) | 0.0040 (9) |
C36 | 0.0207 (11) | 0.0245 (12) | 0.0271 (13) | 0.0042 (9) | 0.0040 (11) | 0.0055 (11) |
N1—C18 | 1.488 (3) | C15—H15B | 0.9900 |
N1—H1B | 0.9100 | C16—C17 | 1.540 (3) |
N1—H1C | 0.9100 | C16—H16A | 0.9900 |
N1—H1D | 0.9100 | C16—H16B | 0.9900 |
N2—C36 | 1.489 (3) | C17—C18 | 1.526 (3) |
N2—H2B | 0.9100 | C17—H17A | 1.0000 |
N2—H2C | 0.9100 | C18—H18A | 0.9900 |
N2—H2D | 0.9100 | C18—H18B | 0.9900 |
S1—C15 | 1.815 (3) | C19—C20 | 1.384 (4) |
S1—C7 | 1.822 (3) | C19—C24 | 1.395 (3) |
S2—C16 | 1.809 (3) | C19—H19A | 0.9500 |
S2—C14 | 1.822 (3) | C20—C21 | 1.385 (4) |
S3—C33 | 1.813 (3) | C20—H20A | 0.9500 |
S3—C25 | 1.827 (3) | C21—C22 | 1.384 (4) |
S4—C34 | 1.804 (3) | C21—H21A | 0.9500 |
S4—C32 | 1.826 (3) | C22—C23 | 1.392 (4) |
C1—C6 | 1.387 (4) | C22—H22A | 0.9500 |
C1—C2 | 1.390 (4) | C23—C24 | 1.393 (3) |
C1—H1A | 0.9500 | C23—H23A | 0.9500 |
C2—C3 | 1.373 (4) | C24—C25 | 1.495 (3) |
C2—H2A | 0.9500 | C25—H25A | 0.9900 |
C3—C4 | 1.387 (4) | C25—H25B | 0.9900 |
C3—H3A | 0.9500 | C26—C31 | 1.390 (4) |
C4—C5 | 1.387 (4) | C26—C27 | 1.391 (4) |
C4—H4A | 0.9500 | C26—H26A | 0.9500 |
C5—C6 | 1.399 (3) | C27—C28 | 1.380 (4) |
C5—H5A | 0.9500 | C27—H27A | 0.9500 |
C6—C7 | 1.502 (3) | C28—C29 | 1.394 (4) |
C7—H7A | 0.9900 | C28—H28A | 0.9500 |
C7—H7B | 0.9900 | C29—C30 | 1.379 (4) |
C8—C9 | 1.378 (4) | C29—H29A | 0.9500 |
C8—C13 | 1.391 (3) | C30—C31 | 1.397 (4) |
C8—H8A | 0.9500 | C30—H30A | 0.9500 |
C9—C10 | 1.388 (4) | C31—C32 | 1.496 (4) |
C9—H9A | 0.9500 | C32—H32A | 0.9900 |
C10—C11 | 1.381 (4) | C32—H32B | 0.9900 |
C10—H10A | 0.9500 | C33—C35 | 1.535 (3) |
C11—C12 | 1.382 (4) | C33—H33A | 0.9900 |
C11—H11A | 0.9500 | C33—H33B | 0.9900 |
C12—C13 | 1.397 (3) | C34—C35 | 1.535 (4) |
C12—H12A | 0.9500 | C34—H34A | 0.9900 |
C13—C14 | 1.499 (4) | C34—H34B | 0.9900 |
C14—H14A | 0.9900 | C35—C36 | 1.536 (3) |
C14—H14B | 0.9900 | C35—H35A | 1.0000 |
C15—C17 | 1.536 (3) | C36—H36A | 0.9900 |
C15—H15A | 0.9900 | C36—H36B | 0.9900 |
C18—N1—H1B | 109.5 | C15—C17—H17A | 108.7 |
C18—N1—H1C | 109.5 | C16—C17—H17A | 108.7 |
H1B—N1—H1C | 109.5 | N1—C18—C17 | 112.7 (2) |
C18—N1—H1D | 109.5 | N1—C18—H18A | 109.1 |
H1B—N1—H1D | 109.5 | C17—C18—H18A | 109.1 |
H1C—N1—H1D | 109.5 | N1—C18—H18B | 109.1 |
C36—N2—H2B | 109.5 | C17—C18—H18B | 109.1 |
C36—N2—H2C | 109.5 | H18A—C18—H18B | 107.8 |
H2B—N2—H2C | 109.5 | C20—C19—C24 | 121.0 (2) |
C36—N2—H2D | 109.5 | C20—C19—H19A | 119.5 |
H2B—N2—H2D | 109.5 | C24—C19—H19A | 119.5 |
H2C—N2—H2D | 109.5 | C21—C20—C19 | 120.2 (3) |
C15—S1—C7 | 101.81 (12) | C21—C20—H20A | 119.9 |
C16—S2—C14 | 101.64 (12) | C19—C20—H20A | 119.9 |
C33—S3—C25 | 102.05 (12) | C22—C21—C20 | 119.6 (3) |
C34—S4—C32 | 101.47 (12) | C22—C21—H21A | 120.2 |
C6—C1—C2 | 120.8 (2) | C20—C21—H21A | 120.2 |
C6—C1—H1A | 119.6 | C21—C22—C23 | 120.1 (3) |
C2—C1—H1A | 119.6 | C21—C22—H22A | 119.9 |
C3—C2—C1 | 120.3 (3) | C23—C22—H22A | 119.9 |
C3—C2—H2A | 119.9 | C22—C23—C24 | 120.8 (2) |
C1—C2—H2A | 119.9 | C22—C23—H23A | 119.6 |
C2—C3—C4 | 119.6 (3) | C24—C23—H23A | 119.6 |
C2—C3—H3A | 120.2 | C23—C24—C19 | 118.3 (2) |
C4—C3—H3A | 120.2 | C23—C24—C25 | 120.9 (2) |
C3—C4—C5 | 120.6 (3) | C19—C24—C25 | 120.8 (2) |
C3—C4—H4A | 119.7 | C24—C25—S3 | 113.18 (18) |
C5—C4—H4A | 119.7 | C24—C25—H25A | 108.9 |
C4—C5—C6 | 120.0 (3) | S3—C25—H25A | 108.9 |
C4—C5—H5A | 120.0 | C24—C25—H25B | 108.9 |
C6—C5—H5A | 120.0 | S3—C25—H25B | 108.9 |
C1—C6—C5 | 118.7 (2) | H25A—C25—H25B | 107.8 |
C1—C6—C7 | 120.3 (2) | C31—C26—C27 | 121.1 (2) |
C5—C6—C7 | 121.1 (2) | C31—C26—H26A | 119.4 |
C6—C7—S1 | 114.41 (18) | C27—C26—H26A | 119.4 |
C6—C7—H7A | 108.7 | C28—C27—C26 | 119.7 (3) |
S1—C7—H7A | 108.7 | C28—C27—H27A | 120.1 |
C6—C7—H7B | 108.7 | C26—C27—H27A | 120.1 |
S1—C7—H7B | 108.7 | C27—C28—C29 | 119.8 (3) |
H7A—C7—H7B | 107.6 | C27—C28—H28A | 120.1 |
C9—C8—C13 | 121.1 (2) | C29—C28—H28A | 120.1 |
C9—C8—H8A | 119.4 | C30—C29—C28 | 120.2 (3) |
C13—C8—H8A | 119.4 | C30—C29—H29A | 119.9 |
C8—C9—C10 | 120.0 (3) | C28—C29—H29A | 119.9 |
C8—C9—H9A | 120.0 | C29—C30—C31 | 120.6 (3) |
C10—C9—H9A | 120.0 | C29—C30—H30A | 119.7 |
C11—C10—C9 | 119.6 (3) | C31—C30—H30A | 119.7 |
C11—C10—H10A | 120.2 | C26—C31—C30 | 118.5 (3) |
C9—C10—H10A | 120.2 | C26—C31—C32 | 119.9 (2) |
C12—C11—C10 | 120.5 (2) | C30—C31—C32 | 121.6 (2) |
C12—C11—H11A | 119.7 | C31—C32—S4 | 113.85 (18) |
C10—C11—H11A | 119.7 | C31—C32—H32A | 108.8 |
C11—C12—C13 | 120.4 (3) | S4—C32—H32A | 108.8 |
C11—C12—H12A | 119.8 | C31—C32—H32B | 108.8 |
C13—C12—H12A | 119.8 | S4—C32—H32B | 108.8 |
C8—C13—C12 | 118.4 (2) | H32A—C32—H32B | 107.7 |
C8—C13—C14 | 120.6 (2) | C35—C33—S3 | 116.00 (18) |
C12—C13—C14 | 121.0 (2) | C35—C33—H33A | 108.3 |
C13—C14—S2 | 113.79 (18) | S3—C33—H33A | 108.3 |
C13—C14—H14A | 108.8 | C35—C33—H33B | 108.3 |
S2—C14—H14A | 108.8 | S3—C33—H33B | 108.3 |
C13—C14—H14B | 108.8 | H33A—C33—H33B | 107.4 |
S2—C14—H14B | 108.8 | C35—C34—S4 | 116.93 (17) |
H14A—C14—H14B | 107.7 | C35—C34—H34A | 108.1 |
C17—C15—S1 | 116.28 (17) | S4—C34—H34A | 108.1 |
C17—C15—H15A | 108.2 | C35—C34—H34B | 108.1 |
S1—C15—H15A | 108.2 | S4—C34—H34B | 108.1 |
C17—C15—H15B | 108.2 | H34A—C34—H34B | 107.3 |
S1—C15—H15B | 108.2 | C34—C35—C33 | 108.0 (2) |
H15A—C15—H15B | 107.4 | C34—C35—C36 | 113.5 (2) |
C17—C16—S2 | 116.57 (18) | C33—C35—C36 | 109.8 (2) |
C17—C16—H16A | 108.2 | C34—C35—H35A | 108.5 |
S2—C16—H16A | 108.2 | C33—C35—H35A | 108.5 |
C17—C16—H16B | 108.2 | C36—C35—H35A | 108.5 |
S2—C16—H16B | 108.2 | N2—C36—C35 | 113.2 (2) |
H16A—C16—H16B | 107.3 | N2—C36—H36A | 108.9 |
C18—C17—C15 | 114.0 (2) | C35—C36—H36A | 108.9 |
C18—C17—C16 | 110.1 (2) | N2—C36—H36B | 108.9 |
C15—C17—C16 | 106.6 (2) | C35—C36—H36B | 108.9 |
C18—C17—H17A | 108.7 | H36A—C36—H36B | 107.8 |
C6—C1—C2—C3 | −0.6 (4) | C24—C19—C20—C21 | 1.2 (4) |
C1—C2—C3—C4 | 0.9 (4) | C19—C20—C21—C22 | −0.8 (4) |
C2—C3—C4—C5 | 0.1 (4) | C20—C21—C22—C23 | 0.1 (4) |
C3—C4—C5—C6 | −1.2 (5) | C21—C22—C23—C24 | 0.2 (4) |
C2—C1—C6—C5 | −0.5 (4) | C22—C23—C24—C19 | 0.2 (4) |
C2—C1—C6—C7 | −179.3 (2) | C22—C23—C24—C25 | −179.4 (2) |
C4—C5—C6—C1 | 1.3 (4) | C20—C19—C24—C23 | −0.9 (4) |
C4—C5—C6—C7 | −179.9 (3) | C20—C19—C24—C25 | 178.7 (2) |
C1—C6—C7—S1 | −119.9 (2) | C23—C24—C25—S3 | −93.7 (3) |
C5—C6—C7—S1 | 61.3 (3) | C19—C24—C25—S3 | 86.8 (3) |
C15—S1—C7—C6 | 60.9 (2) | C33—S3—C25—C24 | 68.4 (2) |
C13—C8—C9—C10 | −0.6 (4) | C31—C26—C27—C28 | 1.1 (4) |
C8—C9—C10—C11 | 0.8 (4) | C26—C27—C28—C29 | −1.4 (4) |
C9—C10—C11—C12 | −0.5 (4) | C27—C28—C29—C30 | 0.5 (5) |
C10—C11—C12—C13 | −0.1 (4) | C28—C29—C30—C31 | 0.7 (5) |
C9—C8—C13—C12 | 0.0 (4) | C27—C26—C31—C30 | 0.1 (4) |
C9—C8—C13—C14 | 179.2 (2) | C27—C26—C31—C32 | 177.7 (2) |
C11—C12—C13—C8 | 0.4 (4) | C29—C30—C31—C26 | −1.0 (4) |
C11—C12—C13—C14 | −178.8 (2) | C29—C30—C31—C32 | −178.7 (3) |
C8—C13—C14—S2 | 94.9 (3) | C26—C31—C32—S4 | 126.3 (2) |
C12—C13—C14—S2 | −86.0 (3) | C30—C31—C32—S4 | −56.1 (3) |
C16—S2—C14—C13 | −66.4 (2) | C34—S4—C32—C31 | −59.1 (2) |
C7—S1—C15—C17 | 71.4 (2) | C25—S3—C33—C35 | 67.4 (2) |
C14—S2—C16—C17 | −66.1 (2) | C32—S4—C34—C35 | −70.6 (2) |
S1—C15—C17—C18 | 49.4 (3) | S4—C34—C35—C33 | −176.04 (18) |
S1—C15—C17—C16 | 171.03 (17) | S4—C34—C35—C36 | −54.1 (3) |
S2—C16—C17—C18 | −67.5 (3) | S3—C33—C35—C34 | −169.65 (17) |
S2—C16—C17—C15 | 168.42 (17) | S3—C33—C35—C36 | 66.1 (3) |
C15—C17—C18—N1 | −84.8 (3) | C34—C35—C36—N2 | 83.5 (3) |
C16—C17—C18—N1 | 155.4 (2) | C33—C35—C36—N2 | −155.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···Cl2i | 0.91 | 2.24 | 3.126 (2) | 163 |
N1—H1C···S1 | 0.91 | 2.59 | 3.216 (2) | 126 |
N1—H1C···Cl2ii | 0.91 | 2.66 | 3.242 (2) | 122 |
N1—H1D···Cl1 | 0.91 | 2.29 | 3.195 (3) | 174 |
N2—H2B···Cl1iii | 0.91 | 2.25 | 3.123 (2) | 161 |
N2—H2C···Cl2 | 0.91 | 2.30 | 3.207 (3) | 174 |
N2—H2D···S4 | 0.91 | 2.62 | 3.238 (2) | 126 |
N2—H2D···Cl1iv | 0.91 | 2.70 | 3.190 (2) | 114 |
Symmetry codes: (i) −x+1, −y+1, z−1; (ii) x+1, y, z−1; (iii) −x+1, −y+1, z; (iv) x−1, y, z. |