Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021337/ob2026sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021337/ob2026Isup2.hkl |
CCDC reference: 613788
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).
C31H33N3OS·C2H6O | Z = 2 |
Mr = 541.76 | F(000) = 580 |
Triclinic, P1 | Dx = 1.206 Mg m−3 |
Hall symbol: -P 1 | Melting point: 417 K |
a = 9.0997 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.9104 (14) Å | Cell parameters from 16690 reflections |
c = 17.540 (2) Å | θ = 2.1–25.0° |
α = 92.876 (10)° | µ = 0.14 mm−1 |
β = 100.365 (10)° | T = 296 K |
γ = 105.41 (1)° | Prism, colourless |
V = 1492.0 (3) Å3 | 0.32 × 0.22 × 0.16 mm |
Stoe IPDS 2 diffractometer | 5247 independent reflections |
Radiation source: fine-focus sealed tube | 2724 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.067 |
Detector resolution: 6.67 pixels mm-1 | θmax = 25.0°, θmin = 2.1° |
rotation method scans | h = −10→10 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −11→11 |
Tmin = 0.955, Tmax = 0.986 | l = −20→20 |
13616 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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 0.87 | w = 1/[σ2(Fo2) + (0.0438P)2] where P = (Fo2 + 2Fc2)/3 |
5234 reflections | (Δ/σ)max = 0.015 |
358 parameters | Δρmax = 0.22 e Å−3 |
2 restraints | Δρmin = −0.20 e Å−3 |
Experimental. IR (ν, cm-1): 3468 (O—H), 3254 (N—H), 1609 (C═N carbazone), 1586 cm-1 (C═N thiazole), 682 (C—S—C thiazole). 1H NMR (CDCl3, δ, p.p.m.): 1.53 (s, 3H, –CH3 on cyclobutane), 2.14 (s, 1H, –NH–), 2.17 (s, 1H, –OH), 2.21 (s, 9H, –CH3 on mesitylene), 2.44–2.59 (m, 4H, –CH2– on cyclobutane), 3.34 (q, j=9.1 Hz, 1H, >C—H on cyclobutane), 6.12 (s, 1H, ═ CH—S), 6.25 (s, 1H, –H on benzoin), 6.74 (s, 2H, aromatics on mesitylene), 7.25–7.42 (m, 8H, aromatics), 7.69 (dd, j=2.2 Hz, 2H, aromatics). 13C NMR (CDCl3, δ, p.p.m.): 170.63, 144.33, 139.78, 137.24, 135.41, 134.96, 130.61, 128.98, 128.95, 128.71, 128.26, 127.01, 126.66, 101.69, 43.52, 43.41, 40.99, 31.51, 24.73, 21.69, 20.66. |
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 | ||
S1 | 0.93534 (9) | 0.30435 (9) | 0.53052 (4) | 0.0544 (2) | |
O1 | 0.5183 (2) | 0.5358 (2) | 0.61084 (12) | 0.0583 (6) | |
H1 | 0.4350 | 0.5582 | 0.6019 | 0.088* | |
N1 | 0.7413 (2) | 0.3847 (2) | 0.43005 (13) | 0.0468 (6) | |
N2 | 0.6920 (3) | 0.3941 (3) | 0.55618 (13) | 0.0556 (7) | |
H2 | 0.6078 | 0.4180 | 0.5418 | 0.067* | |
N3 | 0.7463 (3) | 0.3820 (3) | 0.63242 (13) | 0.0503 (6) | |
C1 | 1.0356 (4) | 0.1768 (4) | 0.13054 (19) | 0.0717 (10) | |
H1A | 1.0324 | 0.2686 | 0.1167 | 0.108* | |
H1B | 1.0953 | 0.1400 | 0.0993 | 0.108* | |
H1C | 1.0831 | 0.1832 | 0.1846 | 0.108* | |
C2 | 0.8716 (3) | 0.0797 (3) | 0.11643 (15) | 0.0494 (7) | |
C3 | 0.8459 (4) | −0.0510 (4) | 0.07691 (16) | 0.0597 (9) | |
H3 | 0.9288 | −0.0736 | 0.0604 | 0.072* | |
C4 | 0.7019 (4) | −0.1496 (4) | 0.06082 (17) | 0.0614 (9) | |
C5 | 0.5809 (4) | −0.1084 (4) | 0.08087 (17) | 0.0641 (9) | |
H5 | 0.4819 | −0.1713 | 0.0685 | 0.077* | |
C6 | 0.6811 (5) | −0.2950 (4) | 0.0219 (2) | 0.0880 (12) | |
H6A | 0.7669 | −0.3293 | 0.0441 | 0.132* | |
H6B | 0.6775 | −0.2905 | −0.0329 | 0.132* | |
H6C | 0.5857 | −0.3574 | 0.0298 | 0.132* | |
C7 | 0.5989 (3) | 0.0228 (4) | 0.11887 (16) | 0.0556 (8) | |
C8 | 0.7473 (3) | 0.1177 (3) | 0.14111 (15) | 0.0482 (7) | |
C9 | 0.4513 (4) | 0.0550 (4) | 0.1324 (2) | 0.0804 (11) | |
H9A | 0.4624 | 0.1538 | 0.1305 | 0.121* | |
H9B | 0.4329 | 0.0292 | 0.1826 | 0.121* | |
H9C | 0.3651 | 0.0024 | 0.0928 | 0.121* | |
C10 | 0.7741 (3) | 0.2589 (3) | 0.18757 (15) | 0.0514 (8) | |
C11 | 0.7637 (4) | 0.3735 (4) | 0.13277 (19) | 0.0759 (10) | |
H11A | 0.7801 | 0.4616 | 0.1630 | 0.114* | |
H11B | 0.6627 | 0.3483 | 0.0993 | 0.114* | |
H11C | 0.8419 | 0.3823 | 0.1017 | 0.114* | |
C12 | 0.9211 (3) | 0.3107 (3) | 0.25517 (15) | 0.0547 (8) | |
H12A | 0.9600 | 0.2352 | 0.2760 | 0.066* | |
H12B | 1.0043 | 0.3843 | 0.2422 | 0.066* | |
C13 | 0.6784 (3) | 0.2659 (3) | 0.25218 (16) | 0.0575 (8) | |
H13A | 0.5947 | 0.3089 | 0.2375 | 0.069* | |
H13B | 0.6408 | 0.1763 | 0.2721 | 0.069* | |
C14 | 0.8242 (3) | 0.3652 (3) | 0.30556 (16) | 0.0525 (8) | |
H14 | 0.8290 | 0.4632 | 0.2972 | 0.063* | |
C15 | 0.8466 (3) | 0.3493 (3) | 0.39036 (15) | 0.0466 (7) | |
C16 | 0.9572 (3) | 0.3031 (3) | 0.43456 (16) | 0.0522 (8) | |
H16 | 1.0347 | 0.2745 | 0.4159 | 0.063* | |
C17 | 0.7769 (3) | 0.3669 (3) | 0.50366 (16) | 0.0467 (7) | |
C18 | 0.6734 (3) | 0.4072 (3) | 0.68492 (16) | 0.0449 (7) | |
C19 | 0.5217 (3) | 0.4494 (3) | 0.67214 (16) | 0.0487 (7) | |
H19 | 0.5195 | 0.5043 | 0.7198 | 0.058* | |
C20 | 0.3861 (3) | 0.3170 (3) | 0.65922 (16) | 0.0476 (7) | |
C21 | 0.3219 (4) | 0.2680 (4) | 0.7208 (2) | 0.0756 (10) | |
H21 | 0.3593 | 0.3187 | 0.7697 | 0.091* | |
C22 | 0.2025 (5) | 0.1445 (5) | 0.7118 (3) | 0.0973 (14) | |
H22 | 0.1603 | 0.1126 | 0.7543 | 0.117* | |
C23 | 0.1473 (5) | 0.0700 (4) | 0.6404 (3) | 0.0889 (12) | |
H23 | 0.0681 | −0.0138 | 0.6341 | 0.107* | |
C24 | 0.2083 (4) | 0.1183 (4) | 0.5778 (3) | 0.0860 (12) | |
H24 | 0.1698 | 0.0678 | 0.5289 | 0.103* | |
C25 | 0.3269 (4) | 0.2417 (4) | 0.5872 (2) | 0.0708 (10) | |
H25 | 0.3672 | 0.2744 | 0.5444 | 0.085* | |
C26 | 0.7409 (3) | 0.3817 (3) | 0.76445 (15) | 0.0466 (7) | |
C27 | 0.7145 (4) | 0.4408 (3) | 0.83240 (17) | 0.0609 (8) | |
H27 | 0.6501 | 0.5001 | 0.8290 | 0.073* | |
C28 | 0.7814 (4) | 0.4136 (4) | 0.90485 (18) | 0.0704 (10) | |
H28 | 0.7608 | 0.4537 | 0.9494 | 0.084* | |
C29 | 0.8766 (4) | 0.3291 (4) | 0.9115 (2) | 0.0815 (11) | |
H29 | 0.9221 | 0.3113 | 0.9604 | 0.098* | |
C30 | 0.9056 (5) | 0.2701 (5) | 0.8458 (2) | 0.0915 (13) | |
H30 | 0.9708 | 0.2116 | 0.8502 | 0.110* | |
C31 | 0.8389 (4) | 0.2963 (4) | 0.77321 (18) | 0.0709 (10) | |
H31 | 0.8605 | 0.2555 | 0.7291 | 0.085* | |
O2 | 0.2460 (3) | 0.1945 (3) | 0.3730 (2) | 0.1140 (10) | |
H2A | 0.3216 | 0.2641 | 0.3853 | 0.171* | |
C32 | 0.2902 (6) | 0.0861 (6) | 0.3398 (3) | 0.1315 (19) | |
H32A | 0.3320 | 0.1172 | 0.2945 | 0.158* | |
H32B | 0.1982 | 0.0075 | 0.3217 | 0.158* | |
C33 | 0.4063 (6) | 0.0365 (6) | 0.3917 (3) | 0.1415 (19) | |
H33A | 0.4996 | 0.1123 | 0.4082 | 0.212* | |
H33B | 0.4292 | −0.0393 | 0.3643 | 0.212* | |
H33C | 0.3657 | 0.0039 | 0.4364 | 0.212* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0524 (5) | 0.0645 (6) | 0.0512 (5) | 0.0263 (4) | 0.0083 (3) | 0.0031 (4) |
O1 | 0.0549 (12) | 0.0659 (15) | 0.0664 (13) | 0.0296 (11) | 0.0197 (10) | 0.0239 (11) |
N1 | 0.0472 (14) | 0.0539 (16) | 0.0417 (14) | 0.0165 (12) | 0.0112 (11) | 0.0061 (11) |
N2 | 0.0523 (15) | 0.080 (2) | 0.0445 (15) | 0.0326 (14) | 0.0134 (12) | 0.0140 (13) |
N3 | 0.0504 (14) | 0.0618 (17) | 0.0428 (14) | 0.0223 (13) | 0.0091 (11) | 0.0096 (12) |
C1 | 0.063 (2) | 0.087 (3) | 0.066 (2) | 0.0131 (19) | 0.0282 (17) | 0.0015 (19) |
C2 | 0.0555 (18) | 0.056 (2) | 0.0403 (16) | 0.0173 (15) | 0.0141 (13) | 0.0096 (15) |
C3 | 0.074 (2) | 0.069 (3) | 0.0439 (18) | 0.032 (2) | 0.0116 (15) | 0.0099 (17) |
C4 | 0.079 (2) | 0.055 (2) | 0.0484 (19) | 0.021 (2) | 0.0042 (17) | 0.0080 (16) |
C5 | 0.058 (2) | 0.067 (3) | 0.057 (2) | 0.0068 (18) | 0.0045 (16) | 0.0034 (18) |
C6 | 0.104 (3) | 0.069 (3) | 0.087 (3) | 0.028 (2) | 0.006 (2) | −0.003 (2) |
C7 | 0.054 (2) | 0.069 (2) | 0.0428 (17) | 0.0151 (17) | 0.0093 (14) | 0.0091 (16) |
C8 | 0.0572 (19) | 0.055 (2) | 0.0362 (15) | 0.0200 (16) | 0.0112 (13) | 0.0119 (14) |
C9 | 0.054 (2) | 0.105 (3) | 0.077 (2) | 0.019 (2) | 0.0102 (17) | −0.004 (2) |
C10 | 0.0602 (19) | 0.058 (2) | 0.0423 (16) | 0.0205 (16) | 0.0164 (14) | 0.0134 (15) |
C11 | 0.108 (3) | 0.071 (3) | 0.059 (2) | 0.035 (2) | 0.0245 (19) | 0.0228 (19) |
C12 | 0.0569 (18) | 0.058 (2) | 0.0500 (18) | 0.0124 (16) | 0.0196 (14) | 0.0055 (15) |
C13 | 0.0558 (19) | 0.073 (2) | 0.0510 (18) | 0.0277 (17) | 0.0143 (14) | 0.0079 (16) |
C14 | 0.0650 (19) | 0.0485 (19) | 0.0484 (18) | 0.0191 (16) | 0.0176 (15) | 0.0063 (14) |
C15 | 0.0498 (17) | 0.0441 (19) | 0.0475 (17) | 0.0130 (14) | 0.0152 (14) | 0.0010 (14) |
C16 | 0.0487 (17) | 0.056 (2) | 0.0564 (18) | 0.0201 (15) | 0.0154 (14) | 0.0010 (15) |
C17 | 0.0432 (16) | 0.0510 (19) | 0.0475 (18) | 0.0150 (14) | 0.0112 (13) | 0.0037 (14) |
C18 | 0.0449 (16) | 0.0454 (18) | 0.0462 (17) | 0.0150 (14) | 0.0103 (13) | 0.0048 (14) |
C19 | 0.0527 (18) | 0.056 (2) | 0.0440 (17) | 0.0220 (16) | 0.0138 (13) | 0.0138 (15) |
C20 | 0.0457 (16) | 0.053 (2) | 0.0508 (18) | 0.0218 (15) | 0.0132 (14) | 0.0113 (15) |
C21 | 0.074 (2) | 0.085 (3) | 0.060 (2) | 0.007 (2) | 0.0123 (18) | 0.021 (2) |
C22 | 0.090 (3) | 0.099 (4) | 0.092 (3) | −0.002 (3) | 0.020 (2) | 0.044 (3) |
C23 | 0.072 (3) | 0.058 (3) | 0.129 (4) | 0.008 (2) | 0.013 (3) | 0.024 (3) |
C24 | 0.067 (2) | 0.082 (3) | 0.100 (3) | 0.012 (2) | 0.012 (2) | −0.019 (2) |
C25 | 0.056 (2) | 0.083 (3) | 0.071 (2) | 0.011 (2) | 0.0221 (17) | −0.005 (2) |
C26 | 0.0446 (16) | 0.0479 (19) | 0.0446 (17) | 0.0113 (14) | 0.0053 (13) | 0.0020 (14) |
C27 | 0.064 (2) | 0.065 (2) | 0.056 (2) | 0.0214 (17) | 0.0129 (16) | 0.0042 (17) |
C28 | 0.078 (2) | 0.082 (3) | 0.046 (2) | 0.015 (2) | 0.0088 (17) | 0.0056 (18) |
C29 | 0.089 (3) | 0.098 (3) | 0.053 (2) | 0.027 (2) | −0.0018 (19) | 0.016 (2) |
C30 | 0.114 (3) | 0.108 (3) | 0.064 (2) | 0.062 (3) | −0.001 (2) | 0.016 (2) |
C31 | 0.083 (2) | 0.084 (3) | 0.053 (2) | 0.043 (2) | 0.0056 (17) | 0.0097 (18) |
O2 | 0.091 (2) | 0.093 (2) | 0.168 (3) | 0.0252 (17) | 0.058 (2) | 0.001 (2) |
C32 | 0.104 (4) | 0.137 (5) | 0.156 (5) | 0.042 (4) | 0.035 (3) | −0.035 (4) |
C33 | 0.130 (5) | 0.136 (5) | 0.164 (5) | 0.046 (4) | 0.030 (4) | 0.022 (4) |
S1—C17 | 1.716 (3) | C13—H13A | 0.9700 |
S1—C16 | 1.730 (3) | C13—H13B | 0.9700 |
O1—C19 | 1.409 (3) | C14—C15 | 1.487 (4) |
O1—H1 | 0.8352 | C14—H14 | 0.9800 |
N1—C17 | 1.306 (3) | C15—C16 | 1.350 (4) |
N1—C15 | 1.385 (3) | C16—H16 | 0.9300 |
N2—N3 | 1.363 (3) | C18—C26 | 1.482 (4) |
N2—C17 | 1.364 (3) | C18—C19 | 1.528 (4) |
N2—H2 | 0.8600 | C19—C20 | 1.518 (4) |
N3—C18 | 1.279 (3) | C19—H19 | 0.9800 |
C1—C2 | 1.515 (4) | C20—C21 | 1.369 (4) |
C1—H1A | 0.9600 | C20—C25 | 1.374 (4) |
C1—H1B | 0.9600 | C21—C22 | 1.384 (5) |
C1—H1C | 0.9600 | C21—H21 | 0.9300 |
C2—C3 | 1.380 (4) | C22—C23 | 1.360 (5) |
C2—C8 | 1.413 (4) | C22—H22 | 0.9300 |
C3—C4 | 1.382 (4) | C23—C24 | 1.369 (5) |
C3—H3 | 0.9300 | C23—H23 | 0.9300 |
C4—C5 | 1.366 (4) | C24—C25 | 1.379 (5) |
C4—C6 | 1.513 (5) | C24—H24 | 0.9300 |
C5—C7 | 1.387 (4) | C25—H25 | 0.9300 |
C5—H5 | 0.9300 | C26—C31 | 1.379 (4) |
C6—H6A | 0.9600 | C26—C27 | 1.389 (4) |
C6—H6B | 0.9600 | C27—C28 | 1.379 (4) |
C6—H6C | 0.9600 | C27—H27 | 0.9300 |
C7—C8 | 1.400 (4) | C28—C29 | 1.351 (5) |
C7—C9 | 1.516 (4) | C28—H28 | 0.9300 |
C8—C10 | 1.521 (4) | C29—C30 | 1.364 (5) |
C9—H9A | 0.9600 | C29—H29 | 0.9300 |
C9—H9B | 0.9600 | C30—C31 | 1.377 (4) |
C9—H9C | 0.9600 | C30—H30 | 0.9300 |
C10—C11 | 1.535 (4) | C31—H31 | 0.9300 |
C10—C13 | 1.558 (4) | O2—C32 | 1.381 (5) |
C10—C12 | 1.569 (4) | O2—H2A | 0.8214 |
C11—H11A | 0.9600 | C32—C33 | 1.471 (6) |
C11—H11B | 0.9600 | C32—H32A | 0.9700 |
C11—H11C | 0.9600 | C32—H32B | 0.9700 |
C12—C14 | 1.529 (4) | C33—H33A | 0.9600 |
C12—H12A | 0.9700 | C33—H33B | 0.9600 |
C12—H12B | 0.9700 | C33—H33C | 0.9600 |
C13—C14 | 1.540 (4) | ||
C17—S1—C16 | 88.17 (14) | C15—C14—H14 | 109.8 |
C19—O1—H1 | 111.2 | C12—C14—H14 | 109.8 |
C17—N1—C15 | 109.9 (2) | C13—C14—H14 | 109.8 |
N3—N2—C17 | 117.2 (2) | C16—C15—N1 | 114.8 (2) |
N3—N2—H2 | 121.4 | C16—C15—C14 | 128.2 (3) |
C17—N2—H2 | 121.4 | N1—C15—C14 | 117.0 (2) |
C18—N3—N2 | 120.6 (2) | C15—C16—S1 | 110.9 (2) |
C2—C1—H1A | 109.5 | C15—C16—H16 | 124.5 |
C2—C1—H1B | 109.5 | S1—C16—H16 | 124.5 |
H1A—C1—H1B | 109.5 | N1—C17—N2 | 122.2 (2) |
C2—C1—H1C | 109.5 | N1—C17—S1 | 116.1 (2) |
H1A—C1—H1C | 109.5 | N2—C17—S1 | 121.7 (2) |
H1B—C1—H1C | 109.5 | N3—C18—C26 | 114.5 (2) |
C3—C2—C8 | 119.9 (3) | N3—C18—C19 | 126.6 (2) |
C3—C2—C1 | 116.9 (3) | C26—C18—C19 | 118.7 (2) |
C8—C2—C1 | 123.2 (3) | O1—C19—C20 | 114.1 (2) |
C2—C3—C4 | 122.6 (3) | O1—C19—C18 | 109.6 (2) |
C2—C3—H3 | 118.7 | C20—C19—C18 | 108.7 (2) |
C4—C3—H3 | 118.7 | O1—C19—H19 | 108.1 |
C5—C4—C3 | 116.8 (3) | C20—C19—H19 | 108.1 |
C5—C4—C6 | 122.3 (3) | C18—C19—H19 | 108.1 |
C3—C4—C6 | 120.9 (3) | C21—C20—C25 | 118.3 (3) |
C4—C5—C7 | 123.0 (3) | C21—C20—C19 | 119.8 (3) |
C4—C5—H5 | 118.5 | C25—C20—C19 | 122.0 (3) |
C7—C5—H5 | 118.5 | C20—C21—C22 | 121.3 (4) |
C4—C6—H6A | 109.5 | C20—C21—H21 | 119.4 |
C4—C6—H6B | 109.5 | C22—C21—H21 | 119.4 |
H6A—C6—H6B | 109.5 | C23—C22—C21 | 119.6 (4) |
C4—C6—H6C | 109.5 | C23—C22—H22 | 120.2 |
H6A—C6—H6C | 109.5 | C21—C22—H22 | 120.2 |
H6B—C6—H6C | 109.5 | C22—C23—C24 | 120.0 (4) |
C5—C7—C8 | 119.9 (3) | C22—C23—H23 | 120.0 |
C5—C7—C9 | 116.3 (3) | C24—C23—H23 | 120.0 |
C8—C7—C9 | 123.8 (3) | C23—C24—C25 | 120.0 (4) |
C7—C8—C2 | 117.4 (3) | C23—C24—H24 | 120.0 |
C7—C8—C10 | 121.7 (3) | C25—C24—H24 | 120.0 |
C2—C8—C10 | 120.8 (3) | C20—C25—C24 | 120.8 (3) |
C7—C9—H9A | 109.5 | C20—C25—H25 | 119.6 |
C7—C9—H9B | 109.5 | C24—C25—H25 | 119.6 |
H9A—C9—H9B | 109.5 | C31—C26—C27 | 116.6 (3) |
C7—C9—H9C | 109.5 | C31—C26—C18 | 119.1 (3) |
H9A—C9—H9C | 109.5 | C27—C26—C18 | 124.2 (3) |
H9B—C9—H9C | 109.5 | C28—C27—C26 | 121.5 (3) |
C8—C10—C11 | 110.6 (2) | C28—C27—H27 | 119.2 |
C8—C10—C13 | 118.3 (2) | C26—C27—H27 | 119.2 |
C11—C10—C13 | 111.0 (3) | C29—C28—C27 | 120.4 (3) |
C8—C10—C12 | 118.2 (2) | C29—C28—H28 | 119.8 |
C11—C10—C12 | 111.0 (3) | C27—C28—H28 | 119.8 |
C13—C10—C12 | 85.60 (19) | C28—C29—C30 | 119.5 (3) |
C10—C11—H11A | 109.5 | C28—C29—H29 | 120.3 |
C10—C11—H11B | 109.5 | C30—C29—H29 | 120.3 |
H11A—C11—H11B | 109.5 | C29—C30—C31 | 120.5 (4) |
C10—C11—H11C | 109.5 | C29—C30—H30 | 119.7 |
H11A—C11—H11C | 109.5 | C31—C30—H30 | 119.7 |
H11B—C11—H11C | 109.5 | C30—C31—C26 | 121.4 (3) |
C14—C12—C10 | 89.9 (2) | C30—C31—H31 | 119.3 |
C14—C12—H12A | 113.7 | C26—C31—H31 | 119.3 |
C10—C12—H12A | 113.7 | C32—O2—H2A | 109.5 |
C14—C12—H12B | 113.7 | O2—C32—C33 | 114.9 (5) |
C10—C12—H12B | 113.7 | O2—C32—H32A | 108.5 |
H12A—C12—H12B | 110.9 | C33—C32—H32A | 108.5 |
C14—C13—C10 | 89.9 (2) | O2—C32—H32B | 108.5 |
C14—C13—H13A | 113.7 | C33—C32—H32B | 108.5 |
C10—C13—H13A | 113.7 | H32A—C32—H32B | 107.5 |
C14—C13—H13B | 113.7 | C32—C33—H33A | 109.5 |
C10—C13—H13B | 113.7 | C32—C33—H33B | 109.5 |
H13A—C13—H13B | 110.9 | H33A—C33—H33B | 109.5 |
C15—C14—C12 | 120.5 (2) | C32—C33—H33C | 109.5 |
C15—C14—C13 | 117.4 (2) | H33A—C33—H33C | 109.5 |
C12—C14—C13 | 87.6 (2) | H33B—C33—H33C | 109.5 |
C17—N2—N3—C18 | 179.4 (3) | N1—C15—C16—S1 | −0.9 (3) |
C8—C2—C3—C4 | −0.9 (4) | C14—C15—C16—S1 | 179.7 (2) |
C1—C2—C3—C4 | 179.5 (3) | C17—S1—C16—C15 | 0.2 (2) |
C2—C3—C4—C5 | 4.7 (4) | C15—N1—C17—N2 | 179.9 (3) |
C2—C3—C4—C6 | −176.0 (3) | C15—N1—C17—S1 | −1.0 (3) |
C3—C4—C5—C7 | −2.9 (4) | N3—N2—C17—N1 | −175.2 (3) |
C6—C4—C5—C7 | 177.8 (3) | N3—N2—C17—S1 | 5.8 (4) |
C4—C5—C7—C8 | −2.6 (4) | C16—S1—C17—N1 | 0.5 (2) |
C4—C5—C7—C9 | 176.4 (3) | C16—S1—C17—N2 | 179.5 (3) |
C5—C7—C8—C2 | 6.2 (4) | N2—N3—C18—C26 | 176.6 (2) |
C9—C7—C8—C2 | −172.6 (3) | N2—N3—C18—C19 | 1.3 (5) |
C5—C7—C8—C10 | −175.9 (2) | N3—C18—C19—O1 | −35.3 (4) |
C9—C7—C8—C10 | 5.3 (4) | C26—C18—C19—O1 | 149.6 (2) |
C3—C2—C8—C7 | −4.6 (4) | N3—C18—C19—C20 | 90.1 (3) |
C1—C2—C8—C7 | 174.9 (3) | C26—C18—C19—C20 | −85.1 (3) |
C3—C2—C8—C10 | 177.5 (2) | O1—C19—C20—C21 | −142.9 (3) |
C1—C2—C8—C10 | −3.0 (4) | C18—C19—C20—C21 | 94.4 (3) |
C7—C8—C10—C11 | −91.6 (3) | O1—C19—C20—C25 | 38.6 (4) |
C2—C8—C10—C11 | 86.2 (3) | C18—C19—C20—C25 | −84.1 (3) |
C7—C8—C10—C13 | 37.9 (4) | C25—C20—C21—C22 | 1.3 (5) |
C2—C8—C10—C13 | −144.3 (2) | C19—C20—C21—C22 | −177.3 (3) |
C7—C8—C10—C12 | 138.8 (3) | C20—C21—C22—C23 | −0.1 (6) |
C2—C8—C10—C12 | −43.4 (3) | C21—C22—C23—C24 | −0.9 (6) |
C8—C10—C12—C14 | −139.7 (3) | C22—C23—C24—C25 | 0.7 (6) |
C11—C10—C12—C14 | 91.0 (3) | C21—C20—C25—C24 | −1.5 (5) |
C13—C10—C12—C14 | −19.8 (2) | C19—C20—C25—C24 | 177.0 (3) |
C8—C10—C13—C14 | 139.5 (2) | C23—C24—C25—C20 | 0.6 (5) |
C11—C10—C13—C14 | −91.2 (3) | N3—C18—C26—C31 | −19.7 (4) |
C12—C10—C13—C14 | 19.7 (2) | C19—C18—C26—C31 | 156.0 (3) |
C10—C12—C14—C15 | 140.7 (3) | N3—C18—C26—C27 | 159.1 (3) |
C10—C12—C14—C13 | 20.0 (2) | C19—C18—C26—C27 | −25.2 (4) |
C10—C13—C14—C15 | −143.6 (3) | C31—C26—C27—C28 | −0.9 (5) |
C10—C13—C14—C12 | −20.2 (2) | C18—C26—C27—C28 | −179.7 (3) |
C17—N1—C15—C16 | 1.2 (4) | C26—C27—C28—C29 | 0.7 (5) |
C17—N1—C15—C14 | −179.3 (2) | C27—C28—C29—C30 | −0.4 (6) |
C12—C14—C15—C16 | 7.5 (5) | C28—C29—C30—C31 | 0.2 (6) |
C13—C14—C15—C16 | 112.1 (3) | C29—C30—C31—C26 | −0.3 (6) |
C12—C14—C15—N1 | −171.9 (3) | C27—C26—C31—C30 | 0.7 (5) |
C13—C14—C15—N1 | −67.4 (3) | C18—C26—C31—C30 | 179.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.84 | 1.84 | 2.674 (3) | 172 |
O2—H2A···O1i | 0.82 | 2.12 | 2.913 (4) | 163 |
N2—H2···O1 | 0.86 | 2.06 | 2.642 (3) | 126 |
C16—H16···O2ii | 0.93 | 2.49 | 3.412 (4) | 177 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z. |