Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805034422/tk6266sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805034422/tk6266Isup2.hkl |
CCDC reference: 289902
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.051
- wR factor = 0.104
- Data-to-parameter ratio = 16.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C5 - C6 ... 1.37 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C5 - C10 ... 1.38 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku Corporation, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
C18H19NO3S | F(000) = 696 |
Mr = 329.41 | Dx = 1.308 Mg m−3 |
Monoclinic, P21/n | Melting point: 157 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71075 Å |
a = 7.224 (2) Å | Cell parameters from 11803 reflections |
b = 19.712 (6) Å | θ = 3.1–27.5° |
c = 12.177 (5) Å | µ = 0.21 mm−1 |
β = 105.272 (14)° | T = 296 K |
V = 1672.7 (10) Å3 | Block, yellow |
Z = 4 | 0.35 × 0.18 × 0.16 mm |
Rigaku R-AXIS RAPID diffractometer | 2183 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.034 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −9→9 |
Tmin = 0.960, Tmax = 0.967 | k = −25→25 |
15968 measured reflections | l = −15→15 |
3834 independent reflections |
Refinement on F2 | w = 1/[0.0001 Fo2 + 3σ(Fo2) + 0.5]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.051 | (Δ/σ)max = 0.002 |
wR(F2) = 0.104 | Δρmax = 0.39 e Å−3 |
S = 1.01 | Δρmin = −0.48 e Å−3 |
3834 reflections | Extinction correction: (Larson, 1970) |
233 parameters | Extinction coefficient: 283 (29) |
H atoms treated by a mixture of independent and constrained refinement |
Geometry. The geometry of the title compound is linear. |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.69928 (8) | 0.73854 (3) | 0.51017 (5) | 0.06109 (17) | |
O1 | 0.49945 (18) | 0.75215 (6) | 0.46384 (12) | 0.0688 (4) | |
O2 | 0.8166 (2) | 0.79161 (8) | 0.57297 (13) | 0.0859 (5) | |
O3 | 0.5873 (3) | 0.58501 (11) | 0.4679 (2) | 0.1391 (10) | |
N1 | −0.2433 (2) | 0.52054 (11) | 0.8601 (2) | 0.0863 (7) | |
C1 | 0.7217 (3) | 0.66817 (12) | 0.6028 (2) | 0.0829 (8) | |
C2 | 0.5802 (4) | 0.61366 (16) | 0.5524 (3) | 0.1001 (12) | |
C5 | 0.1924 (3) | 0.56883 (17) | 0.7069 (2) | 0.0991 (12) | |
C6 | 0.1680 (3) | 0.60453 (12) | 0.7985 (2) | 0.0890 (9) | |
C7 | 0.0277 (3) | 0.58852 (12) | 0.8492 (2) | 0.0766 (8) | |
C8 | −0.0994 (3) | 0.53487 (11) | 0.8108 (2) | 0.0684 (7) | |
C9 | −0.0715 (4) | 0.49784 (12) | 0.7185 (2) | 0.0852 (9) | |
C10 | 0.0728 (5) | 0.51408 (17) | 0.6692 (2) | 0.1025 (11) | |
C11 | −0.2732 (3) | 0.56072 (14) | 0.9522 (2) | 0.1065 (11) | |
C12 | −0.3664 (3) | 0.46175 (13) | 0.8262 (2) | 0.1109 (11) | |
C13 | 0.7997 (2) | 0.71348 (9) | 0.39988 (18) | 0.0521 (5) | |
C14 | 0.9966 (2) | 0.71161 (12) | 0.4187 (2) | 0.0746 (7) | |
C15 | 1.0734 (3) | 0.69366 (12) | 0.3304 (2) | 0.0858 (9) | |
C16 | 0.9557 (3) | 0.67883 (12) | 0.2256 (2) | 0.0762 (8) | |
C17 | 0.7606 (3) | 0.68073 (12) | 0.2072 (2) | 0.0727 (7) | |
C18 | 0.6817 (2) | 0.69792 (10) | 0.29441 (19) | 0.0608 (6) | |
C31 | 0.4563 (7) | 0.6192 (2) | 0.6359 (4) | 0.089 (2) | 0.50 |
C32 | 0.4117 (6) | 0.5776 (2) | 0.5793 (4) | 0.080 (2) | 0.50 |
C41 | 0.3166 (6) | 0.5690 (2) | 0.6238 (4) | 0.075 (2) | 0.50 |
C42 | 0.3610 (6) | 0.6022 (2) | 0.6746 (4) | 0.072 (2) | 0.50 |
H4 | 0.323 (4) | 0.5379 (15) | 0.558 (2) | 0.141 (11)* | |
H3 | 0.430 (3) | 0.6351 (11) | 0.6976 (19) | 0.060 (7)* | |
H6 | 0.2543 | 0.6426 | 0.8275 | 0.108* | |
H7 | 0.0149 | 0.6148 | 0.9151 | 0.092* | |
H9 | −0.1568 | 0.4595 | 0.6900 | 0.101* | |
H10 | 0.0898 | 0.4864 | 0.6058 | 0.126* | |
H11 | 0.7035 | 0.6833 | 0.6750 | 0.100* | |
H12 | 0.8495 | 0.6494 | 0.6147 | 0.100* | |
H14 | 1.0797 | 0.7223 | 0.4943 | 0.087* | |
H15 | 1.2130 | 0.6921 | 0.3429 | 0.104* | |
H16 | 1.0116 | 0.6663 | 0.1634 | 0.095* | |
H17 | 0.6770 | 0.6702 | 0.1317 | 0.086* | |
H18 | 0.5422 | 0.6992 | 0.2827 | 0.072* | |
H111 | −0.4048 | 0.5578 | 0.9544 | 0.132* | |
H112 | −0.1917 | 0.5445 | 1.0228 | 0.132* | |
H113 | −0.2419 | 0.6071 | 0.9408 | 0.132* | |
H121 | −0.4922 | 0.4710 | 0.8349 | 0.133* | |
H122 | −0.3120 | 0.4238 | 0.8731 | 0.133* | |
H123 | −0.3752 | 0.4513 | 0.7480 | 0.133* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0574 (3) | 0.0656 (3) | 0.0562 (3) | 0.0066 (2) | 0.0077 (2) | −0.0034 (2) |
O1 | 0.0539 (8) | 0.0769 (10) | 0.0736 (11) | 0.0150 (6) | 0.0130 (7) | 0.0026 (7) |
O2 | 0.0797 (10) | 0.0896 (11) | 0.0793 (12) | −0.0059 (8) | 0.0050 (9) | −0.0299 (9) |
O3 | 0.192 (2) | 0.0799 (14) | 0.152 (2) | −0.0321 (14) | 0.057 (2) | −0.0066 (14) |
N1 | 0.0935 (15) | 0.0877 (14) | 0.0818 (16) | −0.0164 (11) | 0.0303 (12) | −0.0046 (12) |
C1 | 0.0937 (17) | 0.0958 (18) | 0.0612 (17) | 0.0215 (15) | 0.0237 (14) | 0.0174 (14) |
C2 | 0.104 (2) | 0.093 (2) | 0.113 (2) | 0.0162 (19) | 0.045 (2) | 0.048 (2) |
C5 | 0.088 (2) | 0.105 (2) | 0.116 (2) | 0.0341 (18) | 0.047 (2) | 0.056 (2) |
C6 | 0.0849 (18) | 0.0748 (17) | 0.110 (2) | 0.0078 (13) | 0.0309 (17) | 0.0201 (16) |
C7 | 0.0809 (16) | 0.0728 (15) | 0.0775 (19) | 0.0024 (12) | 0.0235 (14) | −0.0019 (13) |
C8 | 0.0798 (15) | 0.0591 (13) | 0.0631 (16) | 0.0053 (11) | 0.0134 (13) | 0.0052 (11) |
C9 | 0.115 (2) | 0.0653 (15) | 0.0729 (18) | 0.0065 (13) | 0.0200 (16) | −0.0010 (13) |
C10 | 0.141 (2) | 0.104 (2) | 0.072 (2) | 0.048 (2) | 0.0423 (19) | 0.0152 (17) |
C11 | 0.106 (2) | 0.128 (2) | 0.095 (2) | −0.0037 (17) | 0.0439 (19) | −0.0025 (19) |
C12 | 0.103 (2) | 0.092 (2) | 0.137 (3) | −0.0195 (16) | 0.0285 (19) | 0.0139 (19) |
C13 | 0.0447 (10) | 0.0527 (11) | 0.0550 (13) | −0.0006 (8) | 0.0060 (9) | 0.0019 (9) |
C14 | 0.0493 (12) | 0.0900 (17) | 0.0771 (18) | −0.0056 (10) | 0.0038 (12) | −0.0167 (13) |
C15 | 0.0507 (12) | 0.0983 (18) | 0.112 (2) | −0.0055 (12) | 0.0283 (15) | −0.0145 (17) |
C16 | 0.0812 (16) | 0.0766 (16) | 0.081 (2) | −0.0006 (13) | 0.0390 (15) | 0.0024 (13) |
C17 | 0.0728 (15) | 0.0879 (16) | 0.0547 (16) | 0.0073 (12) | 0.0122 (12) | 0.0061 (12) |
C18 | 0.0501 (11) | 0.0730 (14) | 0.0563 (14) | 0.0024 (9) | 0.0088 (11) | −0.0000 (11) |
C31 | 0.094 (4) | 0.079 (4) | 0.086 (5) | 0.008 (3) | 0.009 (4) | 0.013 (4) |
C32 | 0.105 (4) | 0.062 (3) | 0.076 (4) | −0.005 (3) | 0.031 (3) | 0.011 (2) |
C41 | 0.112 (4) | 0.063 (3) | 0.050 (3) | 0.026 (3) | 0.022 (3) | −0.001 (2) |
C42 | 0.100 (4) | 0.048 (3) | 0.053 (3) | 0.024 (3) | −0.007 (3) | −0.020 (2) |
S1—O1 | 1.4301 (13) | C17—C18 | 1.374 (3) |
S1—O2 | 1.4339 (16) | C31—C41 | 1.393 (7) |
S1—C1 | 1.768 (2) | C32—C42 | 1.393 (7) |
S1—C13 | 1.757 (2) | C1—H11 | 0.970 |
O3—C2 | 1.186 (4) | C1—H12 | 0.970 |
N1—C8 | 1.359 (3) | C31—H3 | 0.88 (2) |
N1—C11 | 1.435 (4) | C42—H3 | 0.82 (2) |
N1—C12 | 1.453 (3) | C32—H4 | 1.00 (2) |
C1—C2 | 1.498 (3) | C41—H4 | 1.02 (2) |
C2—C31 | 1.526 (7) | C6—H6 | 0.980 |
C2—C32 | 1.519 (6) | C7—H7 | 0.980 |
C5—C6 | 1.369 (4) | C9—H9 | 0.980 |
C5—C10 | 1.383 (4) | C10—H10 | 0.980 |
C5—C41 | 1.518 (6) | C11—H111 | 0.960 |
C5—C42 | 1.524 (5) | C11—H112 | 0.960 |
C6—C7 | 1.355 (4) | C11—H113 | 0.960 |
C7—C8 | 1.398 (3) | C12—H121 | 0.960 |
C8—C9 | 1.398 (3) | C12—H122 | 0.960 |
C9—C10 | 1.371 (5) | C12—H123 | 0.960 |
C13—C14 | 1.381 (2) | C14—H14 | 0.980 |
C13—C18 | 1.376 (2) | C15—H15 | 0.980 |
C14—C15 | 1.379 (4) | C16—H16 | 0.980 |
C15—C16 | 1.366 (3) | C17—H17 | 0.980 |
C16—C17 | 1.368 (3) | C18—H18 | 0.980 |
O1···C7 | 3.465 (2) | H3···H11 | 2.272 |
O1···C15 | 3.287 (2) | H3···H12 | 3.447 |
O1···C16 | 3.555 (3) | H3···H14 | 3.491 |
O2···C12 | 3.557 (3) | H3···H111 | 3.400 |
O2···C17 | 3.239 (2) | H3···H113 | 3.316 |
O2···C18 | 3.244 (2) | H6···S1 | 3.326 |
O3···C32 | 3.257 (5) | H6···O1 | 3.473 |
O3···C41 | 3.371 (5) | H6···O2 | 3.180 |
N1···C31 | 3.580 (5) | H6···C13 | 2.963 |
N1···C42 | 3.530 (4) | H6···C14 | 3.396 |
C1···C7 | 3.586 (3) | H6···C18 | 3.195 |
C2···C9 | 3.599 (3) | H6···H3 | 2.280 |
C7···O1 | 3.465 (2) | H6···H12 | 3.360 |
C7···C1 | 3.586 (3) | H6···H18 | 3.453 |
C9···C2 | 3.599 (3) | H6···H111 | 3.040 |
C12···O2 | 3.557 (3) | H7···S1 | 3.265 |
C12···C41 | 3.580 (5) | H7···O1 | 2.698 |
C15···O1 | 3.287 (2) | H7···O2 | 3.105 |
C16···O1 | 3.555 (3) | H7···H11 | 3.460 |
C17···O2 | 3.239 (2) | H7···H16 | 3.195 |
C18···O2 | 3.244 (2) | H7···H112 | 3.399 |
C31···N1 | 3.580 (5) | H7···H122 | 2.986 |
C32···O3 | 3.257 (5) | H9···O3 | 3.315 |
C41···O3 | 3.371 (5) | H9···C15 | 3.100 |
C41···C12 | 3.580 (5) | H9···C16 | 3.132 |
C42···N1 | 3.530 (4) | H9···C32 | 3.391 |
S1···H6 | 3.326 | H9···H4 | 2.946 |
S1···H7 | 3.265 | H9···H15 | 3.027 |
S1···H16 | 3.189 | H9···H16 | 3.073 |
O1···H6 | 3.473 | H10···O3 | 3.055 |
O1···H7 | 2.698 | H10···C10 | 3.244 |
O1···H14 | 3.205 | H10···H4 | 2.172 |
O1···H15 | 2.499 | H10···H4 | 3.159 |
O1···H16 | 2.895 | H10···H10 | 2.617 |
O1···H113 | 3.250 | H10···H121 | 3.544 |
O2···H6 | 3.180 | H11···C7 | 3.295 |
O2···H7 | 3.105 | H11···C8 | 3.475 |
O2···H15 | 3.573 | H11···C15 | 3.359 |
O2···H16 | 2.834 | H11···C16 | 3.399 |
O2···H17 | 2.621 | H11···H3 | 2.272 |
O2···H18 | 2.650 | H11···H7 | 3.460 |
O2···H122 | 2.690 | H11···H15 | 3.185 |
O3···H4 | 2.61 (3) | H11···H16 | 3.260 |
O3···H4 | 2.55 (3) | H11···H18 | 3.374 |
O3···H3 | 3.43 (2) | H11···H113 | 3.495 |
O3···H9 | 3.315 | H12···C5 | 2.907 |
O3···H10 | 3.055 | H12···C6 | 2.894 |
O3···H15 | 3.452 | H12···C7 | 3.052 |
O3···H123 | 2.766 | H12···C8 | 3.236 |
N1···H3 | 3.48 (2) | H12···C9 | 3.235 |
N1···H112 | 3.346 | H12···C10 | 3.097 |
C1···H3 | 2.73 (2) | H12···H3 | 3.447 |
C2···H4 | 2.40 (3) | H12···H6 | 3.360 |
C2···H4 | 3.42 (3) | H14···O1 | 3.205 |
C2···H3 | 2.34 (2) | H14···C17 | 3.210 |
C2···H15 | 3.517 | H14···C31 | 3.469 |
C5···H4 | 2.33 (3) | H14···C42 | 3.493 |
C5···H3 | 2.18 (2) | H14···H3 | 3.491 |
C5···H12 | 2.907 | H14···H17 | 2.677 |
C5···H121 | 3.077 | H15···O1 | 2.499 |
C6···H3 | 2.59 (2) | H15···O2 | 3.573 |
C6···H12 | 2.894 | H15···O3 | 3.452 |
C6···H111 | 3.300 | H15···C2 | 3.517 |
C6···H121 | 3.546 | H15···C18 | 3.589 |
C7···H11 | 3.295 | H15···H9 | 3.027 |
C7···H12 | 3.052 | H15···H11 | 3.185 |
C7···H112 | 3.121 | H15···H18 | 2.670 |
C7···H122 | 3.472 | H15···H123 | 3.358 |
C8···H11 | 3.475 | H16···S1 | 3.189 |
C8···H12 | 3.236 | H16···O1 | 2.895 |
C8···H112 | 2.955 | H16···O2 | 2.834 |
C9···H4 | 3.46 (3) | H16···C9 | 3.521 |
C9···H12 | 3.235 | H16···C11 | 3.520 |
C9···H16 | 3.521 | H16···C12 | 3.575 |
C9···H112 | 3.329 | H16···H7 | 3.195 |
C10···H4 | 2.57 (3) | H16···H9 | 3.073 |
C10···H4 | 3.57 (2) | H16···H11 | 3.260 |
C10···H3 | 3.46 (2) | H16···H112 | 3.086 |
C10···H10 | 3.244 | H16···H113 | 3.073 |
C10···H12 | 3.097 | H16···H122 | 2.927 |
C10···H121 | 3.366 | H16···H123 | 3.456 |
C11···H3 | 3.59 (2) | H17···O2 | 2.621 |
C11···H16 | 3.520 | H17···C11 | 3.160 |
C11···H17 | 3.160 | H17···C12 | 3.560 |
C11···H121 | 3.507 | H17···C14 | 3.474 |
C12···H16 | 3.575 | H17···H14 | 2.677 |
C12···H17 | 3.560 | H17···H111 | 3.042 |
C12···H18 | 3.543 | H17···H112 | 3.076 |
C12···H111 | 3.514 | H17···H113 | 2.831 |
C13···H6 | 2.963 | H17···H121 | 3.160 |
C14···H6 | 3.396 | H17···H122 | 3.211 |
C14···H17 | 3.474 | H18···O2 | 2.650 |
C15···H9 | 3.100 | H18···C12 | 3.543 |
C15···H11 | 3.359 | H18···C15 | 3.586 |
C15···H18 | 3.586 | H18···H6 | 3.453 |
C16···H9 | 3.132 | H18···H11 | 3.374 |
C16···H11 | 3.399 | H18···H15 | 2.670 |
C16···H112 | 3.585 | H18···H122 | 3.253 |
C17···H14 | 3.210 | H18···H123 | 3.188 |
C17···H112 | 3.575 | H111···C6 | 3.300 |
C17···H113 | 3.549 | H111···C12 | 3.514 |
C17···H121 | 3.528 | H111···C42 | 3.492 |
C18···H6 | 3.195 | H111···H3 | 3.400 |
C18···H15 | 3.589 | H111···H6 | 3.040 |
C31···H4 | 1.98 (2) | H111···H17 | 3.042 |
C31···H3 | 0.88 (2) | H111···H111 | 3.021 |
C31···H14 | 3.469 | H111···H121 | 2.909 |
C32···H4 | 1.00 (2) | H111···H122 | 3.316 |
C32···H3 | 1.81 (2) | H112···N1 | 3.346 |
C32···H9 | 3.391 | H112···C7 | 3.121 |
C32···H123 | 3.335 | H112···C8 | 2.955 |
C41···H4 | 1.02 (3) | H112···C9 | 3.329 |
C41···H3 | 1.67 (2) | H112···C16 | 3.585 |
C41···H121 | 3.222 | H112···C17 | 3.575 |
C41···H123 | 3.294 | H112···H7 | 3.399 |
C42···H4 | 1.87 (3) | H112···H16 | 3.086 |
C42···H3 | 0.82 (2) | H112···H17 | 3.076 |
C42···H14 | 3.493 | H112···H112 | 3.445 |
C42···H111 | 3.492 | H112···H121 | 3.224 |
C42···H121 | 3.245 | H112···H122 | 3.578 |
C42···H123 | 3.518 | H113···O1 | 3.250 |
H4···O3 | 2.61 (3) | H113···C17 | 3.549 |
H4···O3 | 2.55 (3) | H113···H3 | 3.316 |
H4···C2 | 2.40 (3) | H113···H11 | 3.495 |
H4···C2 | 3.42 (3) | H113···H16 | 3.073 |
H4···C5 | 2.33 (3) | H113···H17 | 2.831 |
H4···C9 | 3.46 (3) | H121···C5 | 3.077 |
H4···C10 | 2.57 (3) | H121···C6 | 3.546 |
H4···C10 | 3.57 (2) | H121···C10 | 3.366 |
H4···C31 | 1.98 (2) | H121···C11 | 3.507 |
H4···C32 | 1.00 (2) | H121···C17 | 3.528 |
H4···C41 | 1.02 (3) | H121···C41 | 3.222 |
H4···C42 | 1.87 (3) | H121···C42 | 3.245 |
H4···H4 | 3.56 (4) | H121···H4 | 3.535 |
H4···H3 | 2.54 (3) | H121···H10 | 3.544 |
H4···H9 | 2.946 | H121···H17 | 3.160 |
H4···H10 | 2.172 | H121···H111 | 2.909 |
H4···H10 | 3.159 | H121···H112 | 3.224 |
H4···H121 | 3.535 | H122···O2 | 2.690 |
H4···H123 | 3.216 | H122···C7 | 3.472 |
H3···O3 | 3.43 (2) | H122···H7 | 2.986 |
H3···N1 | 3.48 (2) | H122···H16 | 2.927 |
H3···C1 | 2.73 (2) | H122···H17 | 3.211 |
H3···C2 | 2.34 (2) | H122···H18 | 3.253 |
H3···C5 | 2.18 (2) | H122···H111 | 3.316 |
H3···C6 | 2.59 (2) | H122···H112 | 3.578 |
H3···C10 | 3.46 (2) | H123···O3 | 2.766 |
H3···C11 | 3.59 (2) | H123···C32 | 3.335 |
H3···C31 | 0.88 (2) | H123···C41 | 3.294 |
H3···C32 | 1.81 (2) | H123···C42 | 3.518 |
H3···C41 | 1.67 (2) | H123···H4 | 3.216 |
H3···C42 | 0.82 (2) | H123···H15 | 3.358 |
H3···H4 | 2.54 (3) | H123···H16 | 3.456 |
H3···H6 | 2.280 | H123···H18 | 3.188 |
O1—S1—O2 | 117.84 (9) | C2—C1—H11 | 110.6 |
O1—S1—C1 | 108.18 (10) | C2—C1—H12 | 107.9 |
O1—S1—C13 | 109.16 (9) | H11—C1—H12 | 109.5 |
O2—S1—C1 | 106.88 (10) | C5—C6—H6 | 118.7 |
O2—S1—C13 | 107.92 (10) | C7—C6—H6 | 119.7 |
C1—S1—C13 | 106.27 (11) | C6—C7—H7 | 119.5 |
C8—N1—C11 | 121.3 (2) | C8—C7—H7 | 118.6 |
C8—N1—C12 | 121.5 (2) | C8—C9—H9 | 118.5 |
C11—N1—C12 | 117.1 (2) | C10—C9—H9 | 120.3 |
S1—C1—C2 | 111.31 (18) | C5—C10—H10 | 119.9 |
O3—C2—C1 | 121.1 (3) | C9—C10—H10 | 118.9 |
O3—C2—C31 | 141.2 (3) | N1—C11—H111 | 110.0 |
O3—C2—C32 | 100.6 (3) | N1—C11—H112 | 109.5 |
C1—C2—C31 | 97.6 (3) | N1—C11—H113 | 108.9 |
C1—C2—C32 | 138.2 (3) | H111—C11—H112 | 109.5 |
C6—C5—C10 | 117.9 (3) | H111—C11—H113 | 109.5 |
C6—C5—C41 | 140.1 (3) | H112—C11—H113 | 109.5 |
C6—C5—C42 | 105.8 (2) | N1—C12—H121 | 110.1 |
C10—C5—C41 | 102.0 (3) | N1—C12—H122 | 109.2 |
C10—C5—C42 | 136.3 (3) | N1—C12—H123 | 109.2 |
C5—C6—C7 | 121.6 (2) | H121—C12—H122 | 109.5 |
C6—C7—C8 | 121.9 (2) | H121—C12—H123 | 109.5 |
N1—C8—C7 | 121.4 (2) | H122—C12—H123 | 109.5 |
N1—C8—C9 | 122.4 (2) | C13—C14—H14 | 119.9 |
C7—C8—C9 | 116.2 (2) | C15—C14—H14 | 121.0 |
C8—C9—C10 | 121.2 (2) | C14—C15—H15 | 119.7 |
C5—C10—C9 | 121.2 (3) | C16—C15—H15 | 120.0 |
S1—C13—C14 | 119.72 (16) | C15—C16—H16 | 119.6 |
S1—C13—C18 | 119.82 (15) | C17—C16—H16 | 119.8 |
C14—C13—C18 | 120.4 (2) | C16—C17—H17 | 120.1 |
C13—C14—C15 | 119.1 (2) | C18—C17—H17 | 119.9 |
C14—C15—C16 | 120.3 (2) | C13—C18—H18 | 119.3 |
C15—C16—C17 | 120.5 (2) | C17—C18—H18 | 120.9 |
C16—C17—C18 | 120.0 (2) | C2—C31—H3 | 153.0 (16) |
C13—C18—C17 | 119.71 (19) | C41—C31—H3 | 91.7 (15) |
C2—C31—C41 | 114.5 (4) | C2—C32—H4 | 144.0 (19) |
C2—C32—C42 | 114.8 (3) | C42—C32—H4 | 101.0 (19) |
C5—C41—C31 | 118.1 (4) | C5—C41—H4 | 132.7 (19) |
C5—C42—C32 | 117.9 (3) | C31—C41—H4 | 109.2 (19) |
S1—C1—H11 | 109.0 | C5—C42—H3 | 135.2 (19) |
S1—C1—H12 | 108.6 | C32—C42—H3 | 106.7 (18) |
O1—S1—C1—C2 | 42.8 (2) | C41—C5—C6—C7 | 177.2 (3) |
O1—S1—C13—C14 | 166.20 (16) | C6—C5—C42—C32 | −177.0 (3) |
O1—S1—C13—C18 | −11.76 (18) | C42—C5—C6—C7 | 179.6 (2) |
O2—S1—C1—C2 | 170.7 (2) | C10—C5—C41—C31 | 179.5 (3) |
O2—S1—C13—C14 | 37.00 (19) | C41—C5—C10—C9 | −176.6 (2) |
O2—S1—C13—C18 | −140.96 (15) | C10—C5—C42—C32 | 5.1 (6) |
C1—S1—C13—C14 | −77.35 (19) | C42—C5—C10—C9 | −179.3 (3) |
C1—S1—C13—C18 | 104.69 (17) | C5—C6—C7—C8 | 0.0 (3) |
C13—S1—C1—C2 | −74.3 (2) | C6—C7—C8—N1 | −178.0 (2) |
C11—N1—C8—C7 | 1.2 (3) | C6—C7—C8—C9 | 1.1 (3) |
C11—N1—C8—C9 | −177.8 (2) | N1—C8—C9—C10 | 178.9 (2) |
C12—N1—C8—C7 | −175.2 (2) | C7—C8—C9—C10 | −0.2 (3) |
C12—N1—C8—C9 | 5.7 (3) | C8—C9—C10—C5 | −1.8 (4) |
S1—C1—C2—O3 | 64.0 (3) | S1—C13—C14—C15 | −178.22 (18) |
S1—C1—C2—C31 | −112.3 (2) | S1—C13—C18—C17 | 177.64 (16) |
S1—C1—C2—C32 | −117.9 (4) | C14—C13—C18—C17 | −0.3 (3) |
O3—C2—C31—C41 | 12.3 (7) | C18—C13—C14—C15 | −0.3 (3) |
O3—C2—C32—C42 | −177.7 (3) | C13—C14—C15—C16 | 0.9 (3) |
C1—C2—C31—C41 | −172.8 (3) | C14—C15—C16—C17 | −0.9 (3) |
C1—C2—C32—C42 | 3.9 (6) | C15—C16—C17—C18 | 0.3 (3) |
C6—C5—C10—C9 | 3.0 (4) | C16—C17—C18—C13 | 0.3 (3) |
C10—C5—C6—C7 | −2.0 (4) | C2—C31—C41—C5 | 177.4 (3) |
C6—C5—C41—C31 | 0.1 (5) | C2—C32—C42—C5 | 179.7 (3) |