Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806018319/bt2087sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806018319/bt2087Isup2.hkl |
CCDC reference: 610721
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C15H13ClN2OS | F(000) = 1264 |
Mr = 304.78 | Dx = 1.472 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7638 reflections |
a = 10.8968 (6) Å | θ = 2.9–28.2° |
b = 32.2055 (19) Å | µ = 0.43 mm−1 |
c = 7.8404 (5) Å | T = 120 K |
β = 90.819 (1)° | Plate, colourless |
V = 2751.2 (3) Å3 | 0.48 × 0.41 × 0.09 mm |
Z = 8 |
Bruker SMART CCD area-detector diffractometer | 6699 independent reflections |
Radiation source: sealed tube | 5819 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
φ and ω scans | θmax = 28.1°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −13→14 |
Tmin = 0.822, Tmax = 0.963 | k = −42→42 |
27617 measured reflections | l = −10→10 |
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)] = 0.042 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.103 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0492P)2 + 1.2928P] where P = (Fo2 + 2Fc2)/3 |
6699 reflections | (Δ/σ)max < 0.001 |
361 parameters | Δρmax = 0.55 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Experimental. 1H NMR (CDCl3, δ, p.p.m.): 2.43 (3H, s, ArCH3), 7.31–7.75 (aromatic), 9.19 (1H, s, broad, NH), 12.76 (1H, s, broad, NH); 13C NMR (CDCl3, δ, p.p.m.): 23.9 (CH3), 126.2 (4 CH), 129.0 (2 CH), 129.20 (2CH), 130.7 (C), 132.1 (C), 134.8 (C) 142.3 (C), 168.1 (C═O), 178.4 (C═S). EIMS m/e: 304, 306, 168.9, 126, 119, 91, 64.9. |
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 | ||
Cl11 | 0.29746 (4) | 0.336235 (14) | 0.45129 (6) | 0.02565 (11) | |
S11 | −0.15383 (4) | 0.354419 (14) | 0.54034 (6) | 0.02431 (11) | |
O11 | 0.16697 (11) | 0.43015 (4) | 0.74365 (18) | 0.0254 (3) | |
N11 | 0.07765 (13) | 0.35563 (4) | 0.6593 (2) | 0.0202 (3) | |
H11H | 0.1393 | 0.3707 | 0.6979 | 0.024* | |
N12 | −0.03382 (13) | 0.41643 (4) | 0.6807 (2) | 0.0202 (3) | |
H12A | −0.1077 | 0.4275 | 0.6836 | 0.024* | |
C11 | 0.09914 (15) | 0.31259 (5) | 0.6321 (2) | 0.0182 (3) | |
C12 | 0.20188 (16) | 0.29965 (5) | 0.5437 (2) | 0.0191 (3) | |
C13 | 0.22932 (16) | 0.25780 (6) | 0.5268 (2) | 0.0217 (4) | |
H1A | 0.3007 | 0.2493 | 0.4681 | 0.026* | |
C14 | 0.15188 (17) | 0.22856 (6) | 0.5963 (2) | 0.0238 (4) | |
H1B | 0.1698 | 0.1998 | 0.5848 | 0.029* | |
C15 | 0.04811 (17) | 0.24102 (5) | 0.6828 (2) | 0.0223 (4) | |
H1C | −0.0054 | 0.2208 | 0.7294 | 0.027* | |
C16 | 0.02241 (16) | 0.28278 (5) | 0.7012 (2) | 0.0210 (4) | |
H1D | −0.0483 | 0.2912 | 0.7617 | 0.025* | |
C17 | −0.02902 (16) | 0.37474 (5) | 0.6304 (2) | 0.0189 (3) | |
C18 | 0.06126 (16) | 0.44253 (5) | 0.7263 (2) | 0.0193 (3) | |
C19 | 0.02784 (15) | 0.48681 (5) | 0.7520 (2) | 0.0180 (3) | |
C110 | 0.10894 (16) | 0.51139 (5) | 0.8465 (2) | 0.0196 (3) | |
H11A | 0.1822 | 0.4995 | 0.8920 | 0.023* | |
C111 | 0.08417 (17) | 0.55299 (5) | 0.8749 (2) | 0.0211 (4) | |
H11B | 0.1401 | 0.5692 | 0.9408 | 0.025* | |
C112 | −0.02205 (16) | 0.57125 (5) | 0.8080 (2) | 0.0198 (3) | |
C113 | −0.10101 (16) | 0.54672 (5) | 0.7106 (2) | 0.0221 (4) | |
H11C | −0.1728 | 0.5588 | 0.6617 | 0.026* | |
C114 | −0.07761 (16) | 0.50503 (5) | 0.6831 (2) | 0.0208 (4) | |
H11D | −0.1336 | 0.4888 | 0.6172 | 0.025* | |
C115 | −0.05196 (18) | 0.61612 (5) | 0.8415 (3) | 0.0264 (4) | |
H11E | −0.0046 | 0.6338 | 0.7649 | 0.040* | |
H11F | −0.0309 | 0.6230 | 0.9602 | 0.040* | |
H11G | −0.1398 | 0.6208 | 0.8214 | 0.040* | |
Cl21 | 0.79864 (4) | 0.169319 (13) | 0.50591 (6) | 0.02395 (11) | |
S21 | 0.34703 (4) | 0.152807 (13) | 0.41795 (6) | 0.02150 (11) | |
O21 | 0.66691 (11) | 0.07166 (4) | 0.27458 (18) | 0.0258 (3) | |
N21 | 0.57621 (13) | 0.14893 (4) | 0.3002 (2) | 0.0194 (3) | |
H21H | 0.6364 | 0.1333 | 0.2633 | 0.023* | |
N22 | 0.46368 (13) | 0.08808 (4) | 0.2971 (2) | 0.0193 (3) | |
H22A | 0.3894 | 0.0775 | 0.2871 | 0.023* | |
C21 | 0.59925 (15) | 0.19209 (5) | 0.3193 (2) | 0.0176 (3) | |
C22 | 0.70340 (15) | 0.20545 (5) | 0.4070 (2) | 0.0176 (3) | |
C23 | 0.73126 (16) | 0.24730 (5) | 0.4210 (2) | 0.0206 (3) | |
H2A | 0.8036 | 0.2560 | 0.4797 | 0.025* | |
C24 | 0.65235 (17) | 0.27627 (5) | 0.3484 (2) | 0.0224 (4) | |
H2B | 0.6701 | 0.3050 | 0.3583 | 0.027* | |
C25 | 0.54752 (16) | 0.26337 (5) | 0.2611 (2) | 0.0213 (4) | |
H2C | 0.4933 | 0.2833 | 0.2122 | 0.026* | |
C26 | 0.52185 (16) | 0.22149 (5) | 0.2453 (2) | 0.0199 (3) | |
H2D | 0.4508 | 0.2128 | 0.1834 | 0.024* | |
C27 | 0.46987 (16) | 0.13049 (5) | 0.3342 (2) | 0.0176 (3) | |
C28 | 0.55936 (16) | 0.06068 (5) | 0.2741 (2) | 0.0186 (3) | |
C29 | 0.52220 (15) | 0.01640 (5) | 0.2540 (2) | 0.0172 (3) | |
C210 | 0.60537 (16) | −0.01371 (5) | 0.3074 (2) | 0.0201 (3) | |
H21A | 0.6826 | −0.0057 | 0.3547 | 0.024* | |
C211 | 0.57626 (16) | −0.05541 (5) | 0.2921 (2) | 0.0216 (4) | |
H21B | 0.6332 | −0.0758 | 0.3310 | 0.026* | |
C212 | 0.46484 (16) | −0.06787 (5) | 0.2206 (2) | 0.0194 (3) | |
C213 | 0.38312 (16) | −0.03745 (5) | 0.1651 (2) | 0.0215 (4) | |
H21C | 0.3071 | −0.0455 | 0.1143 | 0.026* | |
C214 | 0.41065 (16) | 0.00446 (5) | 0.1823 (2) | 0.0207 (4) | |
H21D | 0.3533 | 0.0249 | 0.1452 | 0.025* | |
C215 | 0.43296 (18) | −0.11324 (5) | 0.2026 (3) | 0.0270 (4) | |
H21E | 0.4436 | −0.1219 | 0.0838 | 0.041* | |
H21F | 0.3475 | −0.1176 | 0.2353 | 0.041* | |
H21G | 0.4871 | −0.1297 | 0.2769 | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl11 | 0.0196 (2) | 0.0268 (2) | 0.0307 (2) | −0.00009 (17) | 0.00480 (17) | 0.00412 (17) |
S11 | 0.0183 (2) | 0.0215 (2) | 0.0329 (3) | −0.00071 (16) | −0.00554 (18) | −0.00443 (18) |
O11 | 0.0174 (6) | 0.0184 (6) | 0.0403 (8) | 0.0004 (5) | −0.0021 (5) | −0.0030 (5) |
N11 | 0.0145 (7) | 0.0165 (7) | 0.0295 (8) | −0.0008 (5) | −0.0009 (6) | −0.0049 (6) |
N12 | 0.0141 (7) | 0.0166 (7) | 0.0297 (8) | 0.0015 (5) | −0.0003 (6) | −0.0031 (6) |
C11 | 0.0156 (8) | 0.0176 (8) | 0.0214 (8) | 0.0013 (6) | −0.0022 (6) | −0.0035 (6) |
C12 | 0.0165 (8) | 0.0208 (8) | 0.0198 (8) | −0.0010 (6) | −0.0014 (6) | −0.0007 (6) |
C13 | 0.0186 (9) | 0.0252 (9) | 0.0212 (9) | 0.0055 (7) | 0.0000 (7) | −0.0046 (7) |
C14 | 0.0265 (10) | 0.0181 (8) | 0.0265 (9) | 0.0048 (7) | −0.0048 (7) | −0.0041 (7) |
C15 | 0.0214 (9) | 0.0195 (8) | 0.0260 (9) | −0.0021 (7) | −0.0026 (7) | 0.0006 (7) |
C16 | 0.0167 (8) | 0.0218 (8) | 0.0245 (9) | 0.0000 (7) | 0.0004 (7) | −0.0021 (7) |
C17 | 0.0188 (8) | 0.0170 (8) | 0.0209 (8) | −0.0006 (6) | 0.0016 (7) | −0.0007 (6) |
C18 | 0.0188 (9) | 0.0185 (8) | 0.0206 (8) | −0.0009 (6) | 0.0014 (7) | 0.0002 (6) |
C19 | 0.0163 (8) | 0.0174 (8) | 0.0205 (8) | −0.0011 (6) | 0.0035 (6) | 0.0009 (6) |
C110 | 0.0170 (8) | 0.0204 (8) | 0.0212 (8) | −0.0002 (6) | −0.0002 (7) | 0.0000 (6) |
C111 | 0.0207 (9) | 0.0198 (8) | 0.0230 (9) | −0.0034 (7) | 0.0006 (7) | −0.0040 (7) |
C112 | 0.0212 (9) | 0.0164 (8) | 0.0221 (8) | −0.0009 (6) | 0.0067 (7) | 0.0000 (6) |
C113 | 0.0174 (9) | 0.0218 (8) | 0.0269 (9) | 0.0012 (7) | −0.0005 (7) | 0.0017 (7) |
C114 | 0.0193 (9) | 0.0191 (8) | 0.0238 (9) | −0.0031 (7) | −0.0012 (7) | −0.0018 (7) |
C115 | 0.0269 (10) | 0.0164 (8) | 0.0358 (11) | −0.0001 (7) | 0.0020 (8) | −0.0038 (7) |
Cl21 | 0.0194 (2) | 0.0215 (2) | 0.0309 (2) | 0.00136 (16) | −0.00353 (17) | 0.00422 (16) |
S21 | 0.0176 (2) | 0.0166 (2) | 0.0305 (2) | 0.00141 (15) | 0.00553 (17) | −0.00182 (16) |
O21 | 0.0176 (6) | 0.0159 (6) | 0.0440 (8) | −0.0003 (5) | 0.0026 (6) | −0.0022 (5) |
N21 | 0.0146 (7) | 0.0143 (7) | 0.0293 (8) | 0.0012 (5) | 0.0027 (6) | −0.0026 (6) |
N22 | 0.0151 (7) | 0.0139 (7) | 0.0291 (8) | −0.0015 (5) | 0.0022 (6) | −0.0022 (6) |
C21 | 0.0165 (8) | 0.0148 (7) | 0.0217 (8) | −0.0008 (6) | 0.0034 (6) | −0.0015 (6) |
C22 | 0.0156 (8) | 0.0166 (8) | 0.0206 (8) | 0.0018 (6) | 0.0017 (6) | 0.0025 (6) |
C23 | 0.0198 (9) | 0.0200 (8) | 0.0221 (9) | −0.0041 (7) | 0.0012 (7) | −0.0017 (7) |
C24 | 0.0281 (10) | 0.0138 (8) | 0.0253 (9) | −0.0018 (7) | 0.0045 (7) | 0.0001 (6) |
C25 | 0.0214 (9) | 0.0168 (8) | 0.0257 (9) | 0.0029 (6) | 0.0030 (7) | 0.0027 (7) |
C26 | 0.0165 (8) | 0.0199 (8) | 0.0233 (9) | −0.0004 (6) | −0.0010 (7) | −0.0004 (7) |
C27 | 0.0189 (8) | 0.0136 (7) | 0.0202 (8) | 0.0006 (6) | 0.0009 (6) | −0.0004 (6) |
C28 | 0.0186 (8) | 0.0161 (8) | 0.0211 (8) | 0.0011 (6) | 0.0014 (6) | −0.0005 (6) |
C29 | 0.0177 (8) | 0.0136 (7) | 0.0205 (8) | −0.0007 (6) | 0.0041 (6) | −0.0005 (6) |
C210 | 0.0172 (8) | 0.0190 (8) | 0.0242 (9) | −0.0010 (6) | −0.0005 (7) | 0.0002 (7) |
C211 | 0.0197 (9) | 0.0177 (8) | 0.0273 (9) | 0.0028 (7) | 0.0002 (7) | 0.0012 (7) |
C212 | 0.0208 (9) | 0.0161 (8) | 0.0215 (8) | −0.0015 (6) | 0.0049 (7) | −0.0017 (6) |
C213 | 0.0156 (8) | 0.0214 (8) | 0.0275 (9) | −0.0020 (7) | −0.0003 (7) | −0.0049 (7) |
C214 | 0.0181 (9) | 0.0186 (8) | 0.0255 (9) | 0.0036 (6) | 0.0013 (7) | −0.0007 (7) |
C215 | 0.0268 (10) | 0.0162 (8) | 0.0381 (11) | −0.0024 (7) | 0.0009 (8) | −0.0025 (7) |
Cl11—C12 | 1.7374 (18) | Cl21—C22 | 1.7349 (17) |
S11—C17 | 1.6582 (18) | S21—C27 | 1.6627 (17) |
O11—C18 | 1.225 (2) | O21—C28 | 1.224 (2) |
N11—C17 | 1.332 (2) | N21—C27 | 1.333 (2) |
N11—C11 | 1.422 (2) | N21—C21 | 1.420 (2) |
N11—H11H | 0.8800 | N21—H21H | 0.8800 |
N12—C18 | 1.377 (2) | N22—C28 | 1.380 (2) |
N12—C17 | 1.400 (2) | N22—C27 | 1.398 (2) |
N12—H12A | 0.8800 | N22—H22A | 0.8800 |
C11—C16 | 1.389 (2) | C21—C22 | 1.387 (2) |
C11—C12 | 1.389 (2) | C21—C26 | 1.389 (2) |
C12—C13 | 1.387 (2) | C22—C23 | 1.386 (2) |
C13—C14 | 1.382 (3) | C23—C24 | 1.386 (3) |
C13—H1A | 0.9500 | C23—H2A | 0.9500 |
C14—C15 | 1.386 (3) | C24—C25 | 1.387 (3) |
C14—H1B | 0.9500 | C24—H2B | 0.9500 |
C15—C16 | 1.382 (2) | C25—C26 | 1.383 (2) |
C15—H1C | 0.9500 | C25—H2C | 0.9500 |
C16—H1D | 0.9500 | C26—H2D | 0.9500 |
C18—C19 | 1.486 (2) | C28—C29 | 1.490 (2) |
C19—C110 | 1.392 (2) | C29—C214 | 1.386 (2) |
C19—C114 | 1.392 (2) | C29—C210 | 1.388 (2) |
C110—C111 | 1.385 (2) | C210—C211 | 1.385 (2) |
C110—H11A | 0.9500 | C210—H21A | 0.9500 |
C111—C112 | 1.394 (3) | C211—C212 | 1.389 (2) |
C111—H11B | 0.9500 | C211—H21B | 0.9500 |
C112—C113 | 1.389 (2) | C212—C213 | 1.390 (2) |
C112—C115 | 1.505 (2) | C212—C215 | 1.508 (2) |
C113—C114 | 1.384 (2) | C213—C214 | 1.389 (2) |
C113—H11C | 0.9500 | C213—H21C | 0.9500 |
C114—H11D | 0.9500 | C214—H21D | 0.9500 |
C115—H11E | 0.9800 | C215—H21E | 0.9800 |
C115—H11F | 0.9800 | C215—H21F | 0.9800 |
C115—H11G | 0.9800 | C215—H21G | 0.9800 |
C17—N11—C11 | 124.76 (14) | C27—N21—C21 | 124.63 (14) |
C17—N11—H11H | 117.6 | C27—N21—H21H | 117.7 |
C11—N11—H11H | 117.6 | C21—N21—H21H | 117.7 |
C18—N12—C17 | 128.84 (15) | C28—N22—C27 | 128.15 (15) |
C18—N12—H12A | 115.6 | C28—N22—H22A | 115.9 |
C17—N12—H12A | 115.6 | C27—N22—H22A | 115.9 |
C16—C11—C12 | 118.78 (16) | C22—C21—C26 | 118.89 (15) |
C16—C11—N11 | 120.94 (16) | C22—C21—N21 | 119.88 (15) |
C12—C11—N11 | 120.18 (15) | C26—C21—N21 | 121.17 (15) |
C13—C12—C11 | 121.01 (16) | C23—C22—C21 | 121.20 (15) |
C13—C12—Cl11 | 119.20 (14) | C23—C22—Cl21 | 119.21 (13) |
C11—C12—Cl11 | 119.79 (13) | C21—C22—Cl21 | 119.57 (13) |
C14—C13—C12 | 119.41 (17) | C24—C23—C22 | 119.23 (16) |
C14—C13—H1A | 120.3 | C24—C23—H2A | 120.4 |
C12—C13—H1A | 120.3 | C22—C23—H2A | 120.4 |
C13—C14—C15 | 120.19 (16) | C23—C24—C25 | 120.21 (16) |
C13—C14—H1B | 119.9 | C23—C24—H2B | 119.9 |
C15—C14—H1B | 119.9 | C25—C24—H2B | 119.9 |
C16—C15—C14 | 120.06 (17) | C26—C25—C24 | 120.04 (16) |
C16—C15—H1C | 120.0 | C26—C25—H2C | 120.0 |
C14—C15—H1C | 120.0 | C24—C25—H2C | 120.0 |
C15—C16—C11 | 120.54 (17) | C25—C26—C21 | 120.42 (16) |
C15—C16—H1D | 119.7 | C25—C26—H2D | 119.8 |
C11—C16—H1D | 119.7 | C21—C26—H2D | 119.8 |
N11—C17—N12 | 115.55 (15) | N21—C27—N22 | 115.69 (15) |
N11—C17—S11 | 126.75 (13) | N21—C27—S21 | 126.41 (13) |
N12—C17—S11 | 117.69 (13) | N22—C27—S21 | 117.90 (13) |
O11—C18—N12 | 122.21 (16) | O21—C28—N22 | 122.69 (15) |
O11—C18—C19 | 121.95 (16) | O21—C28—C29 | 122.37 (15) |
N12—C18—C19 | 115.83 (15) | N22—C28—C29 | 114.91 (15) |
C110—C19—C114 | 118.73 (15) | C214—C29—C210 | 119.56 (15) |
C110—C19—C18 | 117.57 (15) | C214—C29—C28 | 122.94 (15) |
C114—C19—C18 | 123.68 (15) | C210—C29—C28 | 117.48 (15) |
C111—C110—C19 | 120.81 (16) | C211—C210—C29 | 120.25 (16) |
C111—C110—H11A | 119.6 | C211—C210—H21A | 119.9 |
C19—C110—H11A | 119.6 | C29—C210—H21A | 119.9 |
C110—C111—C112 | 120.65 (16) | C210—C211—C212 | 120.87 (16) |
C110—C111—H11B | 119.7 | C210—C211—H21B | 119.6 |
C112—C111—H11B | 119.7 | C212—C211—H21B | 119.6 |
C113—C112—C111 | 118.13 (16) | C211—C212—C213 | 118.37 (15) |
C113—C112—C115 | 120.55 (16) | C211—C212—C215 | 121.11 (16) |
C111—C112—C115 | 121.32 (16) | C213—C212—C215 | 120.52 (16) |
C114—C113—C112 | 121.56 (17) | C214—C213—C212 | 121.19 (16) |
C114—C113—H11C | 119.2 | C214—C213—H21C | 119.4 |
C112—C113—H11C | 119.2 | C212—C213—H21C | 119.4 |
C113—C114—C19 | 120.10 (16) | C29—C214—C213 | 119.75 (16) |
C113—C114—H11D | 119.9 | C29—C214—H21D | 120.1 |
C19—C114—H11D | 119.9 | C213—C214—H21D | 120.1 |
C112—C115—H11E | 109.5 | C212—C215—H21E | 109.5 |
C112—C115—H11F | 109.5 | C212—C215—H21F | 109.5 |
H11E—C115—H11F | 109.5 | H21E—C215—H21F | 109.5 |
C112—C115—H11G | 109.5 | C212—C215—H21G | 109.5 |
H11E—C115—H11G | 109.5 | H21E—C215—H21G | 109.5 |
H11F—C115—H11G | 109.5 | H21F—C215—H21G | 109.5 |
C17—N11—C11—C16 | −51.7 (2) | C27—N21—C21—C22 | 130.56 (18) |
C17—N11—C11—C12 | 131.99 (18) | C27—N21—C21—C26 | −52.2 (2) |
C16—C11—C12—C13 | −1.2 (3) | C26—C21—C22—C23 | −0.3 (3) |
N11—C11—C12—C13 | 175.15 (16) | N21—C21—C22—C23 | 177.01 (16) |
C16—C11—C12—Cl11 | 178.42 (13) | C26—C21—C22—Cl21 | 178.00 (13) |
N11—C11—C12—Cl11 | −5.2 (2) | N21—C21—C22—Cl21 | −4.7 (2) |
C11—C12—C13—C14 | 1.3 (3) | C21—C22—C23—C24 | 1.1 (3) |
Cl11—C12—C13—C14 | −178.35 (13) | Cl21—C22—C23—C24 | −177.19 (14) |
C12—C13—C14—C15 | −0.3 (3) | C22—C23—C24—C25 | −0.7 (3) |
C13—C14—C15—C16 | −0.6 (3) | C23—C24—C25—C26 | −0.5 (3) |
C14—C15—C16—C11 | 0.7 (3) | C24—C25—C26—C21 | 1.3 (3) |
C12—C11—C16—C15 | 0.2 (3) | C22—C21—C26—C25 | −0.9 (3) |
N11—C11—C16—C15 | −176.11 (16) | N21—C21—C26—C25 | −178.18 (16) |
C11—N11—C17—N12 | 174.22 (16) | C21—N21—C27—N22 | 176.25 (15) |
C11—N11—C17—S11 | −6.5 (3) | C21—N21—C27—S21 | −4.7 (3) |
C18—N12—C17—N11 | 13.3 (3) | C28—N22—C27—N21 | 19.1 (3) |
C18—N12—C17—S11 | −166.03 (15) | C28—N22—C27—S21 | −160.00 (15) |
C17—N12—C18—O11 | −7.2 (3) | C27—N22—C28—O21 | −4.4 (3) |
C17—N12—C18—C19 | 172.39 (16) | C27—N22—C28—C29 | 173.82 (16) |
O11—C18—C19—C110 | −19.8 (3) | O21—C28—C29—C214 | −151.70 (18) |
N12—C18—C19—C110 | 160.67 (16) | N22—C28—C29—C214 | 30.1 (2) |
O11—C18—C19—C114 | 158.42 (18) | O21—C28—C29—C210 | 27.1 (3) |
N12—C18—C19—C114 | −21.1 (2) | N22—C28—C29—C210 | −151.13 (16) |
C114—C19—C110—C111 | 1.4 (3) | C214—C29—C210—C211 | −1.2 (3) |
C18—C19—C110—C111 | 179.69 (16) | C28—C29—C210—C211 | −179.99 (16) |
C19—C110—C111—C112 | −0.7 (3) | C29—C210—C211—C212 | 1.2 (3) |
C110—C111—C112—C113 | −0.8 (3) | C210—C211—C212—C213 | −0.1 (3) |
C110—C111—C112—C115 | 178.39 (17) | C210—C211—C212—C215 | 179.60 (17) |
C111—C112—C113—C114 | 1.5 (3) | C211—C212—C213—C214 | −0.9 (3) |
C115—C112—C113—C114 | −177.66 (17) | C215—C212—C213—C214 | 179.36 (17) |
C112—C113—C114—C19 | −0.8 (3) | C210—C29—C214—C213 | 0.2 (3) |
C110—C19—C114—C113 | −0.7 (3) | C28—C29—C214—C213 | 178.90 (16) |
C18—C19—C114—C113 | −178.85 (17) | C212—C213—C214—C29 | 0.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11H···O11 | 0.88 | 1.97 | 2.6695 (19) | 136 |
N21—H21H···O21 | 0.88 | 2.01 | 2.6864 (19) | 132 |
N11—H11H···S21i | 0.88 | 2.93 | 3.5545 (16) | 130 |
N12—H12A···O21ii | 0.88 | 2.57 | 3.375 (2) | 153 |
N21—H21H···S11iii | 0.88 | 2.92 | 3.6039 (16) | 135 |
N22—H22A···O11iv | 0.88 | 2.46 | 3.3067 (19) | 163 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x−1, −y+1/2, z+1/2; (iii) x+1, −y+1/2, z−1/2; (iv) x, −y+1/2, z−1/2. |