Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805020350/at6012sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805020350/at6012Isup2.hkl |
CCDC reference: 282225
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C38H56N8S2·2C2H6OS | F(000) = 1824 |
Mr = 845.28 | Dx = 1.149 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2yn | Cell parameters from 38974 reflections |
a = 17.861 (11) Å | θ = 1.5–27.2° |
b = 13.386 (6) Å | µ = 0.24 mm−1 |
c = 20.451 (13) Å | T = 293 K |
β = 91.744 (5)° | Prism, yellow |
V = 4887 (5) Å3 | 0.34 × 0.30 × 0.21 mm |
Z = 4 |
Stoe IPDS 2 diffractometer | 8599 independent reflections |
Radiation source: fine-focus sealed tube | 4458 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
Detector resolution: 6.67 pixels mm-1 | θmax = 25.0°, θmin = 1.5° |
ω scans | h = −21→21 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −15→15 |
Tmin = 0.876, Tmax = 0.953 | l = −24→24 |
25636 measured reflections |
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: inferred from neighbouring sites |
wR(F2) = 0.174 | H-atom parameters constrained |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0946P)2] where P = (Fo2 + 2Fc2)/3 |
8599 reflections | (Δ/σ)max = 0.009 |
548 parameters | Δρmax = 0.80 e Å−3 |
33 restraints | Δρmin = −0.29 e Å−3 |
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 | Occ. (<1) | |
S1 | 0.28838 (6) | 0.45777 (8) | 0.09492 (7) | 0.0910 (4) | |
N1 | 0.42945 (18) | 0.5130 (2) | 0.07941 (16) | 0.0802 (9) | |
H1A | 0.4747 | 0.4988 | 0.0694 | 0.096* | |
H1B | 0.4179 | 0.5730 | 0.0901 | 0.096* | |
N2 | 0.40164 (17) | 0.3497 (2) | 0.06075 (15) | 0.0699 (8) | |
H2 | 0.3699 | 0.3023 | 0.0537 | 0.084* | |
N3 | 0.47759 (16) | 0.3319 (2) | 0.05408 (14) | 0.0665 (8) | |
N4 | 0.38578 (15) | 0.14697 (19) | 0.07573 (12) | 0.0555 (7) | |
C1 | 0.3772 (2) | 0.4417 (3) | 0.07830 (18) | 0.0664 (9) | |
C2 | 0.4971 (2) | 0.2426 (3) | 0.03972 (16) | 0.0625 (9) | |
C3 | 0.4445 (2) | 0.1565 (3) | 0.02739 (17) | 0.0675 (9) | |
H3A | 0.4209 | 0.1644 | −0.0156 | 0.081* | |
H3B | 0.4734 | 0.0951 | 0.0271 | 0.081* | |
C4 | 0.3342 (2) | 0.0661 (3) | 0.05897 (16) | 0.0624 (9) | |
H4A | 0.3611 | 0.0032 | 0.0589 | 0.075* | |
H4B | 0.3127 | 0.0770 | 0.0154 | 0.075* | |
C5 | 0.27279 (19) | 0.0611 (3) | 0.10715 (15) | 0.0589 (8) | |
H5A | 0.2440 | 0.1225 | 0.1052 | 0.071* | |
H5B | 0.2394 | 0.0062 | 0.0958 | 0.071* | |
C6 | 0.5778 (2) | 0.2233 (3) | 0.03113 (17) | 0.0649 (9) | |
H6 | 0.5860 | 0.2060 | −0.0147 | 0.078* | |
C7 | 0.6362 (2) | 0.2996 (3) | 0.05362 (19) | 0.0719 (10) | |
H7A | 0.6202 | 0.3419 | 0.0891 | 0.086* | |
H7B | 0.6558 | 0.3394 | 0.0183 | 0.086* | |
C8 | 0.6889 (2) | 0.2128 (3) | 0.07627 (17) | 0.0665 (9) | |
C9 | 0.6180 (2) | 0.1467 (3) | 0.07553 (17) | 0.0669 (9) | |
H9A | 0.6247 | 0.0821 | 0.0550 | 0.080* | |
H9B | 0.5960 | 0.1395 | 0.1181 | 0.080* | |
C10 | 0.7418 (2) | 0.1829 (4) | 0.0210 (2) | 0.0919 (13) | |
H10A | 0.7135 | 0.1769 | −0.0194 | 0.138* | |
H10B | 0.7652 | 0.1201 | 0.0315 | 0.138* | |
H10C | 0.7796 | 0.2332 | 0.0167 | 0.138* | |
C11 | 0.7330 (2) | 0.2226 (3) | 0.14064 (19) | 0.0724 (10) | |
C12 | 0.7637 (2) | 0.3152 (4) | 0.1604 (2) | 0.0876 (12) | |
C13 | 0.7995 (3) | 0.3217 (5) | 0.2210 (3) | 0.1138 (17) | |
H13 | 0.8191 | 0.3832 | 0.2340 | 0.137* | |
C14 | 0.8080 (3) | 0.2418 (6) | 0.2634 (3) | 0.1155 (19) | |
C15 | 0.7811 (3) | 0.1509 (5) | 0.2414 (3) | 0.1029 (16) | |
H15 | 0.7875 | 0.0952 | 0.2681 | 0.123* | |
C16 | 0.7448 (2) | 0.1390 (4) | 0.1807 (2) | 0.0825 (12) | |
C17 | 0.7237 (3) | 0.0337 (3) | 0.1614 (3) | 0.1063 (15) | |
H17A | 0.7315 | 0.0245 | 0.1156 | 0.159* | |
H17B | 0.6719 | 0.0224 | 0.1703 | 0.159* | |
H17C | 0.7543 | −0.0127 | 0.1861 | 0.159* | |
C18 | 0.7624 (3) | 0.4084 (4) | 0.1185 (3) | 0.1219 (18) | |
H18A | 0.7723 | 0.3908 | 0.0741 | 0.183* | |
H18B | 0.8000 | 0.4541 | 0.1346 | 0.183* | |
H18C | 0.7140 | 0.4393 | 0.1203 | 0.183* | |
C19 | 0.8471 (4) | 0.2510 (6) | 0.3309 (3) | 0.175 (3) | |
H19A | 0.8469 | 0.1873 | 0.3524 | 0.263* | |
H19B | 0.8211 | 0.2990 | 0.3567 | 0.263* | |
H19C | 0.8979 | 0.2725 | 0.3258 | 0.263* | |
S21 | 0.39990 (5) | −0.25809 (7) | 0.14668 (5) | 0.0707 (3) | |
N21 | 0.25586 (16) | −0.3095 (2) | 0.14621 (13) | 0.0622 (7) | |
H21A | 0.2097 | −0.2967 | 0.1537 | 0.075* | |
H21B | 0.2682 | −0.3669 | 0.1311 | 0.075* | |
N22 | 0.28530 (15) | −0.15314 (19) | 0.18139 (13) | 0.0618 (7) | |
H22 | 0.3175 | −0.1062 | 0.1883 | 0.074* | |
N23 | 0.20997 (15) | −0.1373 (2) | 0.19471 (13) | 0.0575 (7) | |
N24 | 0.30364 (14) | 0.04671 (18) | 0.17356 (12) | 0.0520 (6) | |
C21 | 0.30739 (19) | −0.2415 (2) | 0.15788 (15) | 0.0545 (8) | |
C22 | 0.19256 (18) | −0.0493 (2) | 0.21356 (15) | 0.0548 (8) | |
C23 | 0.24486 (19) | 0.0390 (2) | 0.22163 (16) | 0.0592 (8) | |
H23A | 0.2152 | 0.0997 | 0.2196 | 0.071* | |
H23B | 0.2685 | 0.0357 | 0.2649 | 0.071* | |
C24 | 0.35528 (19) | 0.1282 (2) | 0.19045 (15) | 0.0581 (8) | |
H24A | 0.3766 | 0.1178 | 0.2341 | 0.070* | |
H24B | 0.3284 | 0.1911 | 0.1901 | 0.070* | |
C25 | 0.41677 (18) | 0.1319 (3) | 0.14196 (15) | 0.0588 (8) | |
H25A | 0.4509 | 0.1861 | 0.1532 | 0.071* | |
H25B | 0.4449 | 0.0699 | 0.1438 | 0.071* | |
C26 | 0.11384 (19) | −0.0295 (3) | 0.23050 (18) | 0.0638 (9) | |
H26 | 0.1129 | 0.0159 | 0.2681 | 0.077* | |
C27 | 0.05893 (19) | −0.1146 (3) | 0.24037 (16) | 0.0643 (9) | |
H27A | 0.0500 | −0.1289 | 0.2860 | 0.077* | |
H27B | 0.0715 | −0.1752 | 0.2170 | 0.077* | |
C29 | 0.0602 (2) | 0.0092 (3) | 0.1761 (2) | 0.0742 (10) | |
H29A | 0.0731 | −0.0122 | 0.1326 | 0.089* | |
H29B | 0.0520 | 0.0809 | 0.1775 | 0.089* | |
C28 | −0.00416 (19) | −0.0529 (3) | 0.20620 (17) | 0.0663 (9) | |
C30 | −0.0474 (2) | 0.0099 (4) | 0.2558 (2) | 0.1062 (16) | |
H30A | −0.0125 | 0.0433 | 0.2850 | 0.159* | |
H30B | −0.0790 | −0.0331 | 0.2805 | 0.159* | |
H30C | −0.0777 | 0.0586 | 0.2328 | 0.159* | |
C31 | −0.05851 (18) | −0.1063 (3) | 0.15943 (17) | 0.0637 (9) | |
C32 | −0.0865 (2) | −0.2011 (3) | 0.17466 (17) | 0.0685 (10) | |
C33 | −0.1321 (2) | −0.2510 (3) | 0.12988 (19) | 0.0789 (11) | |
H33 | −0.1499 | −0.3139 | 0.1409 | 0.095* | |
C34 | −0.1524 (2) | −0.2122 (4) | 0.06968 (19) | 0.0811 (11) | |
C35 | −0.1286 (2) | −0.1176 (4) | 0.05677 (19) | 0.0825 (12) | |
H35 | −0.1431 | −0.0886 | 0.0170 | 0.099* | |
C36 | −0.0838 (2) | −0.0624 (3) | 0.1001 (2) | 0.0757 (11) | |
C37 | −0.0663 (3) | 0.0441 (3) | 0.0810 (3) | 0.1128 (17) | |
H37A | −0.0738 | 0.0874 | 0.1176 | 0.169* | |
H37B | −0.0989 | 0.0640 | 0.0451 | 0.169* | |
H37C | −0.0152 | 0.0485 | 0.0682 | 0.169* | |
C38 | −0.0703 (2) | −0.2533 (4) | 0.23932 (19) | 0.0948 (14) | |
H38A | −0.0683 | −0.2048 | 0.2739 | 0.142* | |
H38B | −0.0231 | −0.2874 | 0.2377 | 0.142* | |
H38C | −0.1093 | −0.3007 | 0.2473 | 0.142* | |
C39 | −0.1993 (3) | −0.2730 (4) | 0.0210 (2) | 0.1232 (19) | |
H39A | −0.1776 | −0.3382 | 0.0165 | 0.185* | |
H39B | −0.2006 | −0.2399 | −0.0207 | 0.185* | |
H39C | −0.2493 | −0.2793 | 0.0363 | 0.185* | |
S44A | 0.0126 (2) | 0.3200 (2) | 0.16552 (15) | 0.1130 (11) | 0.821 (9) |
O44A | −0.0107 (5) | 0.3603 (8) | 0.1014 (3) | 0.170 (3) | 0.821 (9) |
C44A | 0.0054 (5) | 0.4236 (6) | 0.2215 (4) | 0.125 (3) | 0.821 (9) |
H44A | −0.0464 | 0.4396 | 0.2270 | 0.187* | 0.821 (9) |
H44B | 0.0308 | 0.4806 | 0.2042 | 0.187* | 0.821 (9) |
H44C | 0.0281 | 0.4057 | 0.2630 | 0.187* | 0.821 (9) |
C45A | 0.1122 (5) | 0.3131 (8) | 0.1665 (5) | 0.141 (3) | 0.821 (9) |
H45A | 0.1275 | 0.2656 | 0.1344 | 0.211* | 0.821 (9) |
H45B | 0.1303 | 0.2924 | 0.2090 | 0.211* | 0.821 (9) |
H45C | 0.1324 | 0.3776 | 0.1565 | 0.211* | 0.821 (9) |
S44B | 0.0500 (13) | 0.3003 (12) | 0.1380 (10) | 0.151 (4) | 0.179 (9) |
O44B | 0.023 (3) | 0.347 (4) | 0.0770 (13) | 0.169 (10) | 0.179 (9) |
C44B | −0.005 (2) | 0.384 (3) | 0.188 (2) | 0.126 (9) | 0.179 (9) |
H44D | −0.0569 | 0.3642 | 0.1848 | 0.189* | 0.179 (9) |
H44E | −0.0002 | 0.4510 | 0.1723 | 0.189* | 0.179 (9) |
H44F | 0.0124 | 0.3799 | 0.2325 | 0.189* | 0.179 (9) |
C45B | 0.119 (2) | 0.379 (3) | 0.175 (2) | 0.147 (11) | 0.179 (9) |
H45D | 0.1674 | 0.3624 | 0.1582 | 0.220* | 0.179 (9) |
H45E | 0.1200 | 0.3703 | 0.2212 | 0.220* | 0.179 (9) |
H45F | 0.1078 | 0.4476 | 0.1643 | 0.220* | 0.179 (9) |
S55 | 0.04819 (6) | 0.62514 (9) | 0.08527 (5) | 0.0848 (3) | |
O55 | 0.09531 (17) | 0.6292 (2) | 0.14704 (12) | 0.0981 (9) | |
C55 | 0.0575 (3) | 0.7424 (3) | 0.0477 (2) | 0.1013 (14) | |
H55A | 0.0313 | 0.7918 | 0.0722 | 0.152* | |
H55B | 0.0367 | 0.7396 | 0.0039 | 0.152* | |
H55C | 0.1095 | 0.7599 | 0.0465 | 0.152* | |
C56 | 0.1000 (3) | 0.5530 (4) | 0.0302 (2) | 0.1084 (16) | |
H56A | 0.1012 | 0.4847 | 0.0445 | 0.163* | |
H56B | 0.1502 | 0.5783 | 0.0289 | 0.163* | |
H56C | 0.0768 | 0.5568 | −0.0127 | 0.163* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0648 (6) | 0.0768 (7) | 0.1310 (10) | 0.0079 (5) | −0.0017 (6) | −0.0288 (6) |
N1 | 0.072 (2) | 0.0575 (18) | 0.112 (3) | 0.0049 (17) | 0.0081 (18) | −0.0017 (17) |
N2 | 0.066 (2) | 0.0538 (17) | 0.090 (2) | 0.0037 (15) | 0.0055 (16) | −0.0096 (15) |
N3 | 0.0575 (18) | 0.0665 (18) | 0.0761 (19) | 0.0048 (15) | 0.0112 (15) | −0.0011 (15) |
N4 | 0.0598 (17) | 0.0545 (15) | 0.0522 (15) | 0.0018 (13) | 0.0024 (13) | −0.0105 (12) |
C1 | 0.069 (2) | 0.056 (2) | 0.074 (2) | 0.0032 (19) | −0.0033 (18) | −0.0029 (17) |
C2 | 0.065 (2) | 0.063 (2) | 0.060 (2) | 0.0063 (19) | 0.0141 (16) | −0.0030 (17) |
C3 | 0.070 (2) | 0.067 (2) | 0.066 (2) | 0.0001 (19) | 0.0141 (18) | −0.0158 (17) |
C4 | 0.068 (2) | 0.062 (2) | 0.0560 (19) | −0.0032 (18) | −0.0035 (16) | −0.0136 (16) |
C5 | 0.061 (2) | 0.0581 (19) | 0.0573 (19) | −0.0025 (16) | −0.0085 (16) | −0.0104 (15) |
C6 | 0.069 (2) | 0.070 (2) | 0.0575 (19) | 0.0043 (19) | 0.0200 (17) | −0.0047 (17) |
C7 | 0.069 (2) | 0.069 (2) | 0.080 (2) | 0.003 (2) | 0.0207 (19) | 0.0081 (19) |
C8 | 0.060 (2) | 0.073 (2) | 0.068 (2) | 0.0064 (19) | 0.0222 (18) | −0.0018 (18) |
C9 | 0.069 (2) | 0.064 (2) | 0.068 (2) | 0.0081 (19) | 0.0196 (18) | −0.0083 (17) |
C10 | 0.079 (3) | 0.116 (3) | 0.083 (3) | 0.012 (3) | 0.033 (2) | −0.003 (2) |
C11 | 0.057 (2) | 0.088 (3) | 0.073 (2) | 0.012 (2) | 0.0199 (19) | −0.003 (2) |
C12 | 0.067 (3) | 0.104 (4) | 0.092 (3) | 0.007 (2) | 0.008 (2) | −0.015 (3) |
C13 | 0.088 (4) | 0.127 (5) | 0.127 (5) | 0.008 (3) | 0.006 (3) | −0.030 (4) |
C14 | 0.075 (3) | 0.184 (6) | 0.087 (3) | 0.029 (4) | 0.002 (3) | −0.025 (4) |
C15 | 0.073 (3) | 0.140 (5) | 0.096 (4) | 0.036 (3) | 0.015 (3) | 0.013 (3) |
C16 | 0.059 (2) | 0.111 (4) | 0.078 (3) | 0.020 (2) | 0.015 (2) | 0.007 (3) |
C17 | 0.100 (4) | 0.090 (3) | 0.129 (4) | 0.019 (3) | 0.013 (3) | 0.029 (3) |
C18 | 0.123 (4) | 0.097 (4) | 0.146 (5) | −0.030 (3) | −0.001 (4) | −0.003 (3) |
C19 | 0.141 (6) | 0.264 (9) | 0.119 (5) | 0.047 (6) | −0.027 (4) | −0.031 (5) |
S21 | 0.0622 (6) | 0.0707 (6) | 0.0792 (6) | 0.0075 (5) | 0.0041 (5) | −0.0112 (5) |
N21 | 0.0652 (19) | 0.0483 (15) | 0.0735 (18) | 0.0022 (15) | 0.0062 (14) | −0.0020 (13) |
N22 | 0.0532 (17) | 0.0505 (16) | 0.0817 (19) | 0.0018 (13) | 0.0026 (14) | −0.0079 (14) |
N23 | 0.0490 (16) | 0.0542 (16) | 0.0694 (17) | 0.0021 (13) | 0.0034 (13) | −0.0072 (13) |
N24 | 0.0560 (16) | 0.0496 (15) | 0.0500 (14) | −0.0032 (12) | −0.0046 (12) | −0.0075 (11) |
C21 | 0.062 (2) | 0.0478 (18) | 0.0537 (18) | 0.0058 (17) | 0.0010 (15) | 0.0065 (15) |
C22 | 0.055 (2) | 0.056 (2) | 0.0540 (18) | 0.0019 (16) | −0.0017 (15) | −0.0021 (15) |
C23 | 0.062 (2) | 0.0547 (19) | 0.0604 (19) | −0.0002 (17) | 0.0016 (16) | −0.0118 (15) |
C24 | 0.065 (2) | 0.0575 (19) | 0.0521 (18) | −0.0080 (17) | −0.0024 (16) | −0.0091 (15) |
C25 | 0.055 (2) | 0.0579 (19) | 0.063 (2) | −0.0045 (16) | −0.0041 (16) | −0.0108 (16) |
C26 | 0.058 (2) | 0.062 (2) | 0.072 (2) | 0.0035 (18) | 0.0035 (17) | −0.0159 (17) |
C27 | 0.057 (2) | 0.078 (2) | 0.058 (2) | 0.0032 (19) | 0.0003 (16) | −0.0007 (17) |
C29 | 0.065 (2) | 0.054 (2) | 0.103 (3) | 0.0083 (18) | −0.006 (2) | 0.001 (2) |
C28 | 0.051 (2) | 0.075 (2) | 0.073 (2) | 0.0094 (18) | 0.0015 (17) | −0.0071 (18) |
C30 | 0.070 (3) | 0.128 (4) | 0.121 (4) | 0.025 (3) | 0.005 (3) | −0.046 (3) |
C31 | 0.0444 (19) | 0.078 (2) | 0.068 (2) | 0.0097 (18) | 0.0024 (16) | 0.0056 (19) |
C32 | 0.053 (2) | 0.095 (3) | 0.058 (2) | −0.001 (2) | 0.0034 (16) | 0.009 (2) |
C33 | 0.067 (2) | 0.089 (3) | 0.081 (3) | −0.009 (2) | −0.006 (2) | 0.010 (2) |
C34 | 0.072 (3) | 0.099 (3) | 0.072 (3) | 0.006 (2) | −0.008 (2) | −0.005 (2) |
C35 | 0.073 (3) | 0.105 (3) | 0.069 (2) | 0.019 (3) | −0.012 (2) | 0.013 (2) |
C36 | 0.055 (2) | 0.083 (3) | 0.089 (3) | 0.015 (2) | −0.003 (2) | 0.011 (2) |
C37 | 0.099 (4) | 0.092 (3) | 0.145 (4) | 0.014 (3) | −0.034 (3) | 0.038 (3) |
C38 | 0.077 (3) | 0.130 (4) | 0.077 (3) | −0.031 (3) | −0.006 (2) | 0.030 (3) |
C39 | 0.134 (5) | 0.136 (4) | 0.096 (3) | −0.007 (4) | −0.048 (3) | −0.014 (3) |
S44A | 0.135 (2) | 0.1055 (16) | 0.0966 (17) | −0.0188 (15) | −0.0274 (14) | 0.0090 (12) |
O44A | 0.214 (9) | 0.199 (6) | 0.092 (4) | 0.004 (6) | −0.062 (5) | 0.017 (5) |
C44A | 0.162 (7) | 0.108 (6) | 0.103 (5) | −0.006 (5) | −0.007 (5) | −0.003 (4) |
C45A | 0.132 (7) | 0.184 (10) | 0.106 (5) | 0.026 (8) | −0.022 (5) | 0.000 (7) |
S44B | 0.167 (9) | 0.143 (7) | 0.140 (8) | −0.021 (7) | −0.008 (8) | 0.019 (7) |
O44B | 0.23 (2) | 0.198 (17) | 0.080 (15) | −0.012 (18) | −0.043 (16) | 0.008 (16) |
C44B | 0.165 (18) | 0.086 (17) | 0.127 (19) | −0.001 (16) | −0.001 (18) | −0.032 (15) |
C45B | 0.155 (18) | 0.17 (2) | 0.114 (16) | −0.01 (2) | −0.014 (15) | 0.00 (2) |
S55 | 0.0773 (7) | 0.1003 (8) | 0.0765 (7) | −0.0039 (6) | 0.0000 (5) | 0.0025 (6) |
O55 | 0.098 (2) | 0.136 (3) | 0.0590 (15) | −0.0207 (19) | −0.0130 (14) | 0.0075 (16) |
C55 | 0.107 (4) | 0.102 (3) | 0.096 (3) | 0.010 (3) | 0.015 (3) | 0.012 (3) |
C56 | 0.115 (4) | 0.125 (4) | 0.085 (3) | 0.033 (3) | −0.002 (3) | 0.008 (3) |
S1—C1 | 1.647 (4) | N22—C21 | 1.340 (4) |
N1—C1 | 1.334 (5) | N22—N23 | 1.397 (4) |
N1—H1A | 0.8600 | N22—H22 | 0.8600 |
N1—H1B | 0.8600 | N23—C22 | 1.280 (4) |
N2—C1 | 1.359 (4) | N24—C24 | 1.463 (4) |
N2—N3 | 1.388 (4) | N24—C23 | 1.464 (4) |
N2—H2 | 0.8600 | C22—C26 | 1.482 (5) |
N3—C2 | 1.281 (4) | C22—C23 | 1.513 (5) |
N4—C4 | 1.456 (4) | C23—H23A | 0.9700 |
N4—C25 | 1.462 (4) | C23—H23B | 0.9700 |
N4—C3 | 1.469 (4) | C24—C25 | 1.503 (4) |
C2—C6 | 1.480 (5) | C24—H24A | 0.9700 |
C2—C3 | 1.503 (5) | C24—H24B | 0.9700 |
C3—H3A | 0.9700 | C25—H25A | 0.9700 |
C3—H3B | 0.9700 | C25—H25B | 0.9700 |
C4—C5 | 1.497 (5) | C26—C27 | 1.521 (5) |
C4—H4A | 0.9700 | C26—C29 | 1.536 (5) |
C4—H4B | 0.9700 | C26—H26 | 0.9800 |
C5—N24 | 1.463 (4) | C27—C28 | 1.547 (5) |
C5—H5A | 0.9700 | C27—H27A | 0.9700 |
C5—H5B | 0.9700 | C27—H27B | 0.9700 |
C6—C7 | 1.521 (5) | C29—C28 | 1.560 (5) |
C6—C9 | 1.533 (5) | C29—H29A | 0.9700 |
C6—H6 | 0.9800 | C29—H29B | 0.9700 |
C7—C8 | 1.557 (5) | C28—C31 | 1.520 (5) |
C7—H7A | 0.9700 | C28—C30 | 1.543 (5) |
C7—H7B | 0.9700 | C30—H30A | 0.9600 |
C8—C11 | 1.519 (5) | C30—H30B | 0.9600 |
C8—C9 | 1.544 (5) | C30—H30C | 0.9600 |
C8—C10 | 1.548 (5) | C31—C32 | 1.402 (5) |
C9—H9A | 0.9700 | C31—C36 | 1.410 (5) |
C9—H9B | 0.9700 | C32—C33 | 1.380 (5) |
C10—H10A | 0.9600 | C32—C38 | 1.516 (5) |
C10—H10B | 0.9600 | C33—C34 | 1.375 (5) |
C10—H10C | 0.9600 | C33—H33 | 0.9300 |
C11—C16 | 1.400 (6) | C34—C35 | 1.365 (6) |
C11—C12 | 1.410 (6) | C34—C39 | 1.518 (6) |
C12—C13 | 1.380 (7) | C35—C36 | 1.388 (6) |
C12—C18 | 1.512 (7) | C35—H35 | 0.9300 |
C13—C14 | 1.383 (8) | C36—C37 | 1.514 (6) |
C13—H13 | 0.9300 | C37—H37A | 0.9600 |
C14—C15 | 1.379 (8) | C37—H37B | 0.9600 |
C14—C19 | 1.533 (8) | C37—H37C | 0.9600 |
C15—C16 | 1.391 (7) | C38—H38A | 0.9600 |
C15—H15 | 0.9300 | C38—H38B | 0.9600 |
C16—C17 | 1.508 (6) | C38—H38C | 0.9600 |
C17—H17A | 0.9600 | C39—H39A | 0.9600 |
C17—H17B | 0.9600 | C39—H39B | 0.9600 |
C17—H17C | 0.9600 | C39—H39C | 0.9600 |
C18—H18A | 0.9600 | S55—O55 | 1.497 (3) |
C18—H18B | 0.9600 | S55—C55 | 1.758 (5) |
C18—H18C | 0.9600 | S55—C56 | 1.766 (5) |
C19—H19A | 0.9600 | C55—H55A | 0.9600 |
C19—H19B | 0.9600 | C55—H55B | 0.9600 |
C19—H19C | 0.9600 | C55—H55C | 0.9600 |
S21—C21 | 1.690 (4) | C56—H56A | 0.9600 |
N21—C21 | 1.312 (4) | C56—H56B | 0.9600 |
N21—H21A | 0.8600 | C56—H56C | 0.9600 |
N21—H21B | 0.8600 | ||
C1—N1—H1A | 120.0 | C24—N24—C23 | 110.7 (2) |
C1—N1—H1B | 120.0 | C5—N24—C23 | 112.0 (3) |
H1A—N1—H1B | 120.0 | N21—C21—N22 | 117.7 (3) |
C1—N2—N3 | 120.3 (3) | N21—C21—S21 | 124.6 (3) |
C1—N2—H2 | 119.9 | N22—C21—S21 | 117.7 (3) |
N3—N2—H2 | 119.9 | N23—C22—C26 | 118.5 (3) |
C2—N3—N2 | 117.1 (3) | N23—C22—C23 | 126.6 (3) |
C4—N4—C25 | 109.6 (3) | C26—C22—C23 | 114.9 (3) |
C4—N4—C3 | 111.5 (2) | N24—C23—C22 | 115.8 (3) |
C25—N4—C3 | 112.2 (3) | N24—C23—H23A | 108.3 |
N1—C1—N2 | 115.0 (3) | C22—C23—H23A | 108.3 |
N1—C1—S1 | 125.5 (3) | N24—C23—H23B | 108.3 |
N2—C1—S1 | 119.5 (3) | C22—C23—H23B | 108.3 |
N3—C2—C6 | 117.5 (3) | H23A—C23—H23B | 107.4 |
N3—C2—C3 | 125.5 (3) | N24—C24—C25 | 109.7 (2) |
C6—C2—C3 | 116.9 (3) | N24—C24—H24A | 109.7 |
N4—C3—C2 | 114.2 (3) | C25—C24—H24A | 109.7 |
N4—C3—H3A | 108.7 | N24—C24—H24B | 109.7 |
C2—C3—H3A | 108.7 | C25—C24—H24B | 109.7 |
N4—C3—H3B | 108.7 | H24A—C24—H24B | 108.2 |
C2—C3—H3B | 108.7 | N4—C25—C24 | 110.6 (3) |
H3A—C3—H3B | 107.6 | N4—C25—H25A | 109.5 |
N4—C4—C5 | 110.5 (3) | C24—C25—H25A | 109.5 |
N4—C4—H4A | 109.6 | N4—C25—H25B | 109.5 |
C5—C4—H4A | 109.6 | C24—C25—H25B | 109.5 |
N4—C4—H4B | 109.6 | H25A—C25—H25B | 108.1 |
C5—C4—H4B | 109.6 | C22—C26—C27 | 121.1 (3) |
H4A—C4—H4B | 108.1 | C22—C26—C29 | 117.8 (3) |
N24—C5—C4 | 110.8 (3) | C27—C26—C29 | 87.6 (3) |
N24—C5—H5A | 109.5 | C22—C26—H26 | 109.5 |
C4—C5—H5A | 109.5 | C27—C26—H26 | 109.5 |
N24—C5—H5B | 109.5 | C29—C26—H26 | 109.5 |
C4—C5—H5B | 109.5 | C26—C27—C28 | 90.2 (3) |
H5A—C5—H5B | 108.1 | C26—C27—H27A | 113.6 |
C2—C6—C7 | 120.6 (3) | C28—C27—H27A | 113.6 |
C2—C6—C9 | 119.1 (3) | C26—C27—H27B | 113.6 |
C7—C6—C9 | 88.0 (3) | C28—C27—H27B | 113.6 |
C2—C6—H6 | 109.1 | H27A—C27—H27B | 110.9 |
C7—C6—H6 | 109.1 | C26—C29—C28 | 89.2 (3) |
C9—C6—H6 | 109.1 | C26—C29—H29A | 113.8 |
C6—C7—C8 | 89.5 (3) | C28—C29—H29A | 113.8 |
C6—C7—H7A | 113.7 | C26—C29—H29B | 113.8 |
C8—C7—H7A | 113.7 | C28—C29—H29B | 113.8 |
C6—C7—H7B | 113.7 | H29A—C29—H29B | 111.0 |
C8—C7—H7B | 113.7 | C31—C28—C30 | 110.3 (3) |
H7A—C7—H7B | 111.0 | C31—C28—C27 | 118.4 (3) |
C11—C8—C9 | 117.5 (3) | C30—C28—C27 | 111.5 (3) |
C11—C8—C10 | 110.1 (3) | C31—C28—C29 | 117.8 (3) |
C9—C8—C10 | 111.3 (3) | C30—C28—C29 | 111.0 (3) |
C11—C8—C7 | 119.0 (3) | C27—C28—C29 | 85.9 (3) |
C9—C8—C7 | 86.4 (3) | C28—C30—H30A | 109.5 |
C10—C8—C7 | 110.7 (3) | C28—C30—H30B | 109.5 |
C6—C9—C8 | 89.5 (3) | H30A—C30—H30B | 109.5 |
C6—C9—H9A | 113.7 | C28—C30—H30C | 109.5 |
C8—C9—H9A | 113.7 | H30A—C30—H30C | 109.5 |
C6—C9—H9B | 113.7 | H30B—C30—H30C | 109.5 |
C8—C9—H9B | 113.7 | C32—C31—C36 | 117.5 (3) |
H9A—C9—H9B | 111.0 | C32—C31—C28 | 120.7 (3) |
C8—C10—H10A | 109.5 | C36—C31—C28 | 121.8 (3) |
C8—C10—H10B | 109.5 | C33—C32—C31 | 119.9 (3) |
H10A—C10—H10B | 109.5 | C33—C32—C38 | 116.7 (4) |
C8—C10—H10C | 109.5 | C31—C32—C38 | 123.5 (4) |
H10A—C10—H10C | 109.5 | C34—C33—C32 | 123.1 (4) |
H10B—C10—H10C | 109.5 | C34—C33—H33 | 118.5 |
C16—C11—C12 | 119.0 (4) | C32—C33—H33 | 118.5 |
C16—C11—C8 | 120.2 (4) | C35—C34—C33 | 116.7 (4) |
C12—C11—C8 | 120.8 (4) | C35—C34—C39 | 122.6 (4) |
C13—C12—C11 | 118.6 (5) | C33—C34—C39 | 120.7 (4) |
C13—C12—C18 | 117.1 (5) | C34—C35—C36 | 123.2 (4) |
C11—C12—C18 | 124.3 (4) | C34—C35—H35 | 118.4 |
C12—C13—C14 | 123.6 (6) | C36—C35—H35 | 118.4 |
C12—C13—H13 | 118.2 | C35—C36—C31 | 119.4 (4) |
C14—C13—H13 | 118.2 | C35—C36—C37 | 117.1 (4) |
C15—C14—C13 | 116.6 (5) | C31—C36—C37 | 123.4 (4) |
C15—C14—C19 | 120.7 (7) | C36—C37—H37A | 109.5 |
C13—C14—C19 | 122.7 (7) | C36—C37—H37B | 109.5 |
C14—C15—C16 | 122.7 (5) | H37A—C37—H37B | 109.5 |
C14—C15—H15 | 118.6 | C36—C37—H37C | 109.5 |
C16—C15—H15 | 118.6 | H37A—C37—H37C | 109.5 |
C15—C16—C11 | 119.3 (5) | H37B—C37—H37C | 109.5 |
C15—C16—C17 | 116.5 (5) | C32—C38—H38A | 109.5 |
C11—C16—C17 | 124.2 (4) | C32—C38—H38B | 109.5 |
C16—C17—H17A | 109.5 | H38A—C38—H38B | 109.5 |
C16—C17—H17B | 109.5 | C32—C38—H38C | 109.5 |
H17A—C17—H17B | 109.5 | H38A—C38—H38C | 109.5 |
C16—C17—H17C | 109.5 | H38B—C38—H38C | 109.5 |
H17A—C17—H17C | 109.5 | C34—C39—H39A | 109.5 |
H17B—C17—H17C | 109.5 | C34—C39—H39B | 109.5 |
C12—C18—H18A | 109.5 | H39A—C39—H39B | 109.5 |
C12—C18—H18B | 109.5 | C34—C39—H39C | 109.5 |
H18A—C18—H18B | 109.5 | H39A—C39—H39C | 109.5 |
C12—C18—H18C | 109.5 | H39B—C39—H39C | 109.5 |
H18A—C18—H18C | 109.5 | O55—S55—C55 | 106.2 (2) |
H18B—C18—H18C | 109.5 | O55—S55—C56 | 105.4 (2) |
C14—C19—H19A | 109.5 | C55—S55—C56 | 98.7 (2) |
C14—C19—H19B | 109.5 | S55—C55—H55A | 109.5 |
H19A—C19—H19B | 109.5 | S55—C55—H55B | 109.5 |
C14—C19—H19C | 109.5 | H55A—C55—H55B | 109.5 |
H19A—C19—H19C | 109.5 | S55—C55—H55C | 109.5 |
H19B—C19—H19C | 109.5 | H55A—C55—H55C | 109.5 |
C21—N21—H21A | 120.0 | H55B—C55—H55C | 109.5 |
C21—N21—H21B | 120.0 | S55—C56—H56A | 109.5 |
H21A—N21—H21B | 120.0 | S55—C56—H56B | 109.5 |
C21—N22—N23 | 120.0 (3) | H56A—C56—H56B | 109.5 |
C21—N22—H22 | 120.0 | S55—C56—H56C | 109.5 |
N23—N22—H22 | 120.0 | H56A—C56—H56C | 109.5 |
C22—N23—N22 | 116.3 (3) | H56B—C56—H56C | 109.5 |
C24—N24—C5 | 109.7 (2) | ||
C1—N2—N3—C2 | 177.6 (3) | C4—C5—N24—C23 | −178.6 (3) |
N3—N2—C1—N1 | 8.6 (5) | N23—N22—C21—N21 | 2.2 (4) |
N3—N2—C1—S1 | −172.4 (3) | N23—N22—C21—S21 | −176.7 (2) |
N2—N3—C2—C6 | 178.7 (3) | N22—N23—C22—C26 | −178.0 (3) |
N2—N3—C2—C3 | 2.1 (5) | N22—N23—C22—C23 | 1.2 (5) |
C4—N4—C3—C2 | 176.6 (3) | C24—N24—C23—C22 | −173.8 (3) |
C25—N4—C3—C2 | −60.1 (4) | C5—N24—C23—C22 | 63.3 (4) |
N3—C2—C3—N4 | −46.1 (5) | N23—C22—C23—N24 | 36.2 (5) |
C6—C2—C3—N4 | 137.3 (3) | C26—C22—C23—N24 | −144.6 (3) |
C25—N4—C4—C5 | 57.9 (3) | C5—N24—C24—C25 | −58.1 (3) |
C3—N4—C4—C5 | −177.3 (3) | C23—N24—C24—C25 | 177.7 (3) |
N4—C4—C5—N24 | −58.1 (4) | C4—N4—C25—C24 | −58.7 (3) |
N3—C2—C6—C7 | 13.7 (5) | C3—N4—C25—C24 | 176.9 (3) |
C3—C2—C6—C7 | −169.4 (3) | N24—C24—C25—N4 | 59.1 (4) |
N3—C2—C6—C9 | 120.1 (4) | N23—C22—C26—C27 | 13.7 (5) |
C3—C2—C6—C9 | −62.9 (4) | C23—C22—C26—C27 | −165.6 (3) |
C2—C6—C7—C8 | 142.3 (3) | N23—C22—C26—C29 | −91.6 (4) |
C9—C6—C7—C8 | 19.3 (2) | C23—C22—C26—C29 | 89.2 (4) |
C6—C7—C8—C11 | −138.8 (3) | C22—C26—C27—C28 | −141.7 (3) |
C6—C7—C8—C9 | −19.2 (2) | C29—C26—C27—C28 | −20.3 (3) |
C6—C7—C8—C10 | 92.3 (3) | C22—C26—C29—C28 | 144.3 (3) |
C2—C6—C9—C8 | −143.7 (3) | C27—C26—C29—C28 | 20.1 (3) |
C7—C6—C9—C8 | −19.5 (2) | C26—C27—C28—C31 | 139.5 (3) |
C11—C8—C9—C6 | 140.0 (3) | C26—C27—C28—C30 | −91.0 (3) |
C10—C8—C9—C6 | −91.8 (3) | C26—C27—C28—C29 | 20.0 (3) |
C7—C8—C9—C6 | 19.0 (2) | C26—C29—C28—C31 | −139.9 (3) |
C9—C8—C11—C16 | 41.4 (4) | C26—C29—C28—C30 | 91.7 (3) |
C10—C8—C11—C16 | −87.4 (4) | C26—C29—C28—C27 | −19.8 (2) |
C7—C8—C11—C16 | 143.4 (3) | C30—C28—C31—C32 | −88.7 (4) |
C9—C8—C11—C12 | −139.8 (3) | C27—C28—C31—C32 | 41.4 (4) |
C10—C8—C11—C12 | 91.4 (4) | C29—C28—C31—C32 | 142.6 (3) |
C7—C8—C11—C12 | −37.9 (5) | C30—C28—C31—C36 | 90.2 (4) |
C16—C11—C12—C13 | −4.9 (6) | C27—C28—C31—C36 | −139.7 (3) |
C8—C11—C12—C13 | 176.3 (4) | C29—C28—C31—C36 | −38.6 (5) |
C16—C11—C12—C18 | 173.0 (4) | C36—C31—C32—C33 | 5.1 (5) |
C8—C11—C12—C18 | −5.8 (6) | C28—C31—C32—C33 | −176.0 (3) |
C11—C12—C13—C14 | 0.9 (7) | C36—C31—C32—C38 | −174.0 (4) |
C18—C12—C13—C14 | −177.2 (5) | C28—C31—C32—C38 | 4.9 (5) |
C12—C13—C14—C15 | 2.7 (8) | C31—C32—C33—C34 | −0.2 (6) |
C12—C13—C14—C19 | −179.2 (5) | C38—C32—C33—C34 | 179.0 (4) |
C13—C14—C15—C16 | −2.3 (7) | C32—C33—C34—C35 | −3.6 (6) |
C19—C14—C15—C16 | 179.6 (4) | C32—C33—C34—C39 | 176.7 (4) |
C14—C15—C16—C11 | −1.7 (6) | C33—C34—C35—C36 | 2.4 (6) |
C14—C15—C16—C17 | 175.7 (4) | C39—C34—C35—C36 | −178.0 (4) |
C12—C11—C16—C15 | 5.3 (5) | C34—C35—C36—C31 | 2.6 (6) |
C8—C11—C16—C15 | −175.9 (3) | C34—C35—C36—C37 | −175.9 (4) |
C12—C11—C16—C17 | −171.8 (4) | C32—C31—C36—C35 | −6.3 (5) |
C8—C11—C16—C17 | 6.9 (5) | C28—C31—C36—C35 | 174.8 (3) |
C21—N22—N23—C22 | −176.2 (3) | C32—C31—C36—C37 | 172.1 (4) |
C4—C5—N24—C24 | 58.0 (3) | C28—C31—C36—C37 | −6.8 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N3 | 0.86 | 2.26 | 2.629 (4) | 106 |
N1—H1B···S21i | 0.86 | 2.56 | 3.407 (4) | 167 |
N2—H2···N4 | 0.86 | 2.14 | 2.747 (4) | 127 |
N21—H21A···O55ii | 0.86 | 2.27 | 2.983 (5) | 140 |
N21—H21A···N23 | 0.86 | 2.29 | 2.649 (4) | 105 |
N21—H21B···S1ii | 0.86 | 2.49 | 3.344 (4) | 172 |
N22—H22···N24 | 0.86 | 2.08 | 2.701 (4) | 128 |
C6—H6···S21iii | 0.98 | 2.81 | 3.700 (4) | 152 |
C24—H24A···O55iv | 0.97 | 2.47 | 3.413 (5) | 163 |
C44A—H44B···O55 | 0.96 | 2.59 | 3.553 (9) | 175 |
C55—H55B···O44Av | 0.96 | 2.57 | 3.425 (9) | 149 |
C56—H56C···O44Av | 0.96 | 2.41 | 3.297 (9) | 154 |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) −x+1, −y, −z; (iv) −x+1/2, y−1/2, −z+1/2; (v) −x, −y+1, −z. |
Compound | N1-C1 | C1-S1 | N2-C1 | N2-N3 | S1-C1-N1 | Ref. |
I | 1.321 (5) | 1.669 (4) | 1.352 (5) | 1.390 (4) | 125.3 (3) | (a) |
II | 1.325 (3) | 1.688 (2) | 1.343 (3) | 1.374 (2) | 123.1 (2) | (b) |
III | 1.353 (3) | 1.689 (2) | 1.353 (3) | 1.373 (2) | 122.6 (2) | (c) |
IV | 1.342 (2) | 1.696 (2) | 1.342 (2) | 1.342 (2) | 122.5 (1) | (d) |
V | 1.319 (3) | 1.674 (2) | 1.352 (2) | 1.373 (2) | 123.3 (2) | (e) |
VI | 1.319 (3) | 1.673 (2) | 1.350 (2) | 1.382 (2) | 124.8 (2) | (f) |
Notes: (a) This work (averaged values), (I), C42H68N8O2S4, 1,4-bis{[(2Z)-2-(3-mesityl-3-methylcyclobutyl)-2-one thiosemicarbazone]ethyl} piperazine dimethyl sulfoxide disolvate; (b) Kokila et al., 1995), (II), C11H17N3O4S, 3,4,5-trimethoxybenzaldehyde thiosemicarbazone monohydrate; (c) Zhu et al., 1999), (III), C22H32N6O4S4, 2,2'-ethylenedioxydibenzaldehyde bis(thiosemicarbazone) bis(dimethyl sulfoxide); (d) Moers et al., 1999), (IV), C16H34N6O4S2, 1,4,7,1O-tetraoxacyclododecane-acetone thiosemicarbazone (1/2); (e) Wu et al., 2000), (V), C16H26N8O2S2, terephthaldehyde thiosemicarbazone bis-N,N-dimethylformamide; (f) Sampath et al., 2003), (VI), C22H28N4S, 1-N-methyl-t-3-isopropyl-r-2,c-6-diphenylpiperidone thiosemicarbazone. |