Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807005983/hg2181sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807005983/hg2181Isup2.hkl |
CCDC reference: 640359
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.002 Å
- R factor = 0.037
- wR factor = 0.102
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 600 Deg. PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C1 .. 5.58 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.
C15H13ClN2OS | Z = 6 |
Mr = 304.78 | F(000) = 948 |
Triclinic, P1 | Dx = 1.356 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.4839 (6) Å | Cell parameters from 20189 reflections |
b = 15.1584 (12) Å | θ = 3.6–25.7° |
c = 18.1998 (15) Å | µ = 0.39 mm−1 |
α = 105.659 (6)° | T = 173 K |
β = 95.941 (6)° | Block, colourless |
γ = 90.878 (6)° | 0.47 × 0.44 × 0.42 mm |
V = 2239.3 (3) Å3 |
Stoe IPDS-II two-circle diffractometer | 8331 independent reflections |
Radiation source: fine-focus sealed tube | 7078 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
ω scans | θmax = 25.6°, θmin = 3.5° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −10→10 |
Tmin = 0.837, Tmax = 0.853 | k = −18→18 |
20945 measured reflections | l = −22→22 |
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)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.0603P)2 + 0.3669P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
8331 reflections | Δρmax = 0.31 e Å−3 |
557 parameters | Δρmin = −0.35 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0110 (8) |
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 | 0.40643 (5) | 0.86256 (3) | 0.96937 (2) | 0.02844 (11) | |
Cl1 | 0.86759 (8) | 1.25974 (3) | 0.90554 (4) | 0.06210 (18) | |
N1 | 0.46452 (15) | 0.80226 (8) | 0.82351 (7) | 0.0234 (3) | |
H2 | 0.612 (2) | 0.9773 (15) | 0.9344 (12) | 0.040 (6)* | |
C1 | 0.50038 (18) | 0.86279 (10) | 0.89257 (9) | 0.0219 (3) | |
O2 | 0.81472 (13) | 0.83221 (7) | 0.85405 (7) | 0.0303 (3) | |
N2 | 0.62135 (15) | 0.92975 (9) | 0.89924 (7) | 0.0219 (3) | |
C2 | 0.77315 (18) | 0.91032 (10) | 0.87952 (8) | 0.0219 (3) | |
C3 | 0.34275 (19) | 0.72876 (11) | 0.81509 (10) | 0.0288 (4) | |
H3A | 0.3701 | 0.6953 | 0.8535 | 0.043* | |
H3B | 0.3378 | 0.6864 | 0.7635 | 0.043* | |
H3C | 0.2394 | 0.7557 | 0.8227 | 0.043* | |
C11 | 0.52101 (19) | 0.81255 (11) | 0.75379 (9) | 0.0254 (3) | |
C12 | 0.5939 (2) | 0.73969 (12) | 0.70683 (10) | 0.0339 (4) | |
H12 | 0.6074 | 0.6838 | 0.7205 | 0.041* | |
C13 | 0.6462 (2) | 0.75051 (14) | 0.63984 (10) | 0.0449 (5) | |
H13 | 0.6937 | 0.7010 | 0.6068 | 0.054* | |
C14 | 0.6299 (3) | 0.83275 (15) | 0.62053 (10) | 0.0468 (5) | |
H14 | 0.6698 | 0.8403 | 0.5756 | 0.056* | |
C15 | 0.5550 (2) | 0.90391 (14) | 0.66720 (10) | 0.0411 (5) | |
H15 | 0.5423 | 0.9599 | 0.6537 | 0.049* | |
C16 | 0.4986 (2) | 0.89353 (12) | 0.73337 (9) | 0.0312 (4) | |
H16 | 0.4449 | 0.9417 | 0.7645 | 0.037* | |
C21 | 0.88361 (18) | 0.99247 (10) | 0.89274 (8) | 0.0219 (3) | |
C22 | 0.8281 (2) | 1.07826 (11) | 0.89161 (9) | 0.0264 (3) | |
H22 | 0.7179 | 1.0862 | 0.8815 | 0.032* | |
C23 | 0.9371 (2) | 1.15183 (12) | 0.90557 (10) | 0.0347 (4) | |
C24 | 1.0984 (2) | 1.14157 (13) | 0.91957 (10) | 0.0382 (4) | |
H24 | 1.1711 | 1.1927 | 0.9292 | 0.046* | |
C25 | 1.1520 (2) | 1.05570 (13) | 0.91937 (10) | 0.0354 (4) | |
H25 | 1.2626 | 1.0479 | 0.9284 | 0.042* | |
C26 | 1.04625 (19) | 0.98110 (12) | 0.90611 (9) | 0.0274 (3) | |
H26 | 1.0841 | 0.9224 | 0.9061 | 0.033* | |
S1A | 0.76096 (5) | 0.20117 (3) | 0.66039 (2) | 0.02984 (11) | |
Cl1A | 1.22556 (6) | 0.56900 (3) | 0.55785 (3) | 0.04881 (14) | |
O1A | 1.15865 (13) | 0.14911 (7) | 0.54159 (7) | 0.0293 (3) | |
N1A | 0.80852 (15) | 0.12242 (9) | 0.51474 (7) | 0.0243 (3) | |
C1A | 0.84817 (18) | 0.18952 (10) | 0.57970 (9) | 0.0221 (3) | |
N2A | 0.96958 (15) | 0.25319 (9) | 0.57832 (7) | 0.0222 (3) | |
H2A | 0.961 (2) | 0.3056 (15) | 0.6049 (11) | 0.036 (5)* | |
C2A | 1.12033 (18) | 0.22892 (10) | 0.55971 (8) | 0.0216 (3) | |
C3A | 0.6911 (2) | 0.05006 (11) | 0.51449 (10) | 0.0317 (4) | |
H3D | 0.7257 | 0.0210 | 0.5551 | 0.048* | |
H3E | 0.6811 | 0.0040 | 0.4646 | 0.048* | |
H3F | 0.5882 | 0.0769 | 0.5237 | 0.048* | |
C11A | 0.86167 (18) | 0.12243 (11) | 0.44172 (9) | 0.0248 (3) | |
C12A | 0.9279 (2) | 0.04409 (12) | 0.39835 (10) | 0.0328 (4) | |
H12A | 0.9382 | −0.0090 | 0.4164 | 0.039* | |
C13A | 0.9786 (2) | 0.04519 (14) | 0.32827 (11) | 0.0441 (5) | |
H13A | 1.0216 | −0.0081 | 0.2978 | 0.053* | |
C14A | 0.9668 (3) | 0.12319 (15) | 0.30245 (10) | 0.0459 (5) | |
H14A | 1.0056 | 0.1240 | 0.2555 | 0.055* | |
C15A | 0.8981 (2) | 0.20023 (14) | 0.34535 (10) | 0.0407 (4) | |
H15A | 0.8888 | 0.2534 | 0.3274 | 0.049* | |
C16A | 0.8432 (2) | 0.19923 (12) | 0.41445 (9) | 0.0310 (4) | |
H16A | 0.7932 | 0.2510 | 0.4430 | 0.037* | |
C21A | 1.23259 (17) | 0.30702 (10) | 0.56335 (8) | 0.0203 (3) | |
C22A | 1.18021 (19) | 0.39166 (10) | 0.55666 (8) | 0.0237 (3) | |
H22A | 1.0701 | 0.4009 | 0.5480 | 0.028* | |
C23A | 1.2919 (2) | 0.46209 (11) | 0.56292 (9) | 0.0279 (3) | |
C24A | 1.4536 (2) | 0.44952 (12) | 0.57359 (9) | 0.0305 (4) | |
H24A | 1.5283 | 0.4985 | 0.5780 | 0.037* | |
C25A | 1.50404 (19) | 0.36436 (12) | 0.57768 (9) | 0.0286 (4) | |
H25A | 1.6144 | 0.3545 | 0.5835 | 0.034* | |
C26A | 1.39567 (18) | 0.29330 (11) | 0.57336 (8) | 0.0240 (3) | |
H26A | 1.4317 | 0.2355 | 0.5772 | 0.029* | |
S1B | 0.09382 (5) | 0.51358 (3) | 0.32438 (2) | 0.03131 (12) | |
Cl1B | 0.57057 (7) | 0.87131 (4) | 0.20713 (4) | 0.06312 (19) | |
N1B | 0.14457 (15) | 0.43419 (9) | 0.17956 (8) | 0.0259 (3) | |
C1B | 0.18155 (18) | 0.50175 (10) | 0.24410 (9) | 0.0231 (3) | |
O2B | 0.49417 (13) | 0.46105 (7) | 0.21950 (7) | 0.0312 (3) | |
N2B | 0.30160 (15) | 0.56586 (9) | 0.24149 (7) | 0.0228 (3) | |
H2B | 0.288 (3) | 0.6180 (15) | 0.2669 (12) | 0.044 (6)* | |
C2B | 0.45565 (18) | 0.54020 (10) | 0.22959 (8) | 0.0221 (3) | |
C3B | 0.0257 (2) | 0.36139 (12) | 0.17765 (11) | 0.0373 (4) | |
H3G | 0.0587 | 0.3314 | 0.2178 | 0.056* | |
H3H | 0.0166 | 0.3160 | 0.1274 | 0.056* | |
H3I | −0.0773 | 0.3883 | 0.1865 | 0.056* | |
C11B | 0.20780 (19) | 0.43136 (11) | 0.10805 (9) | 0.0260 (3) | |
C12B | 0.2973 (2) | 0.35765 (11) | 0.07481 (10) | 0.0315 (4) | |
H12B | 0.3157 | 0.3094 | 0.0984 | 0.038* | |
C13B | 0.3590 (2) | 0.35603 (13) | 0.00699 (10) | 0.0388 (4) | |
H13B | 0.4214 | 0.3066 | −0.0158 | 0.047* | |
C14B | 0.3305 (2) | 0.42591 (15) | −0.02794 (10) | 0.0441 (5) | |
H14B | 0.3743 | 0.4246 | −0.0742 | 0.053* | |
C15B | 0.2381 (3) | 0.49778 (14) | 0.00467 (11) | 0.0448 (5) | |
H15B | 0.2176 | 0.5452 | −0.0197 | 0.054* | |
C16B | 0.1755 (2) | 0.50065 (12) | 0.07250 (10) | 0.0346 (4) | |
H16B | 0.1113 | 0.5494 | 0.0946 | 0.042* | |
C21B | 0.56976 (17) | 0.61605 (10) | 0.22897 (8) | 0.0208 (3) | |
C22B | 0.51943 (19) | 0.69936 (11) | 0.21842 (9) | 0.0256 (3) | |
H22B | 0.4096 | 0.7100 | 0.2109 | 0.031* | |
C23B | 0.6334 (2) | 0.76643 (12) | 0.21908 (10) | 0.0316 (4) | |
C24B | 0.7945 (2) | 0.75228 (13) | 0.22870 (10) | 0.0335 (4) | |
H24B | 0.8704 | 0.7993 | 0.2293 | 0.040* | |
C25B | 0.84264 (19) | 0.66843 (12) | 0.23743 (9) | 0.0313 (4) | |
H25B | 0.9526 | 0.6574 | 0.2430 | 0.038* | |
C26B | 0.73196 (19) | 0.60025 (11) | 0.23809 (9) | 0.0266 (3) | |
H26B | 0.7661 | 0.5432 | 0.2447 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0309 (2) | 0.0241 (2) | 0.0312 (2) | −0.00231 (16) | 0.01444 (16) | 0.00524 (16) |
Cl1 | 0.0694 (4) | 0.0259 (3) | 0.0973 (5) | −0.0015 (2) | 0.0227 (3) | 0.0230 (3) |
N1 | 0.0225 (7) | 0.0181 (6) | 0.0286 (7) | −0.0036 (5) | 0.0046 (5) | 0.0043 (5) |
C1 | 0.0201 (7) | 0.0174 (7) | 0.0280 (8) | 0.0012 (6) | 0.0049 (6) | 0.0049 (6) |
O2 | 0.0266 (6) | 0.0217 (6) | 0.0400 (6) | 0.0026 (5) | 0.0064 (5) | 0.0028 (5) |
N2 | 0.0219 (7) | 0.0179 (6) | 0.0238 (6) | −0.0020 (5) | 0.0077 (5) | 0.0001 (5) |
C2 | 0.0208 (8) | 0.0229 (8) | 0.0211 (7) | −0.0002 (6) | 0.0023 (6) | 0.0043 (6) |
C3 | 0.0259 (8) | 0.0205 (8) | 0.0382 (9) | −0.0068 (6) | 0.0046 (7) | 0.0049 (7) |
C11 | 0.0236 (8) | 0.0247 (8) | 0.0248 (7) | −0.0059 (6) | 0.0019 (6) | 0.0022 (6) |
C12 | 0.0352 (10) | 0.0288 (9) | 0.0323 (9) | −0.0020 (7) | 0.0059 (7) | −0.0014 (7) |
C13 | 0.0493 (12) | 0.0454 (11) | 0.0309 (9) | −0.0034 (9) | 0.0138 (8) | −0.0082 (8) |
C14 | 0.0537 (13) | 0.0567 (13) | 0.0260 (9) | −0.0173 (10) | 0.0086 (8) | 0.0042 (8) |
C15 | 0.0527 (12) | 0.0400 (10) | 0.0309 (9) | −0.0122 (9) | 0.0019 (8) | 0.0119 (8) |
C16 | 0.0340 (9) | 0.0296 (9) | 0.0288 (8) | −0.0035 (7) | 0.0034 (7) | 0.0061 (7) |
C21 | 0.0233 (8) | 0.0234 (8) | 0.0182 (7) | −0.0026 (6) | 0.0054 (6) | 0.0034 (6) |
C22 | 0.0258 (8) | 0.0254 (8) | 0.0290 (8) | 0.0000 (6) | 0.0090 (6) | 0.0070 (6) |
C23 | 0.0419 (10) | 0.0258 (9) | 0.0378 (9) | −0.0060 (7) | 0.0122 (8) | 0.0088 (7) |
C24 | 0.0368 (10) | 0.0395 (10) | 0.0359 (9) | −0.0191 (8) | 0.0047 (8) | 0.0069 (8) |
C25 | 0.0241 (9) | 0.0492 (11) | 0.0324 (9) | −0.0108 (8) | 0.0001 (7) | 0.0123 (8) |
C26 | 0.0222 (8) | 0.0344 (9) | 0.0253 (8) | −0.0016 (7) | 0.0034 (6) | 0.0073 (7) |
S1A | 0.0297 (2) | 0.0278 (2) | 0.0342 (2) | −0.00114 (16) | 0.01508 (17) | 0.00805 (17) |
Cl1A | 0.0541 (3) | 0.0252 (2) | 0.0761 (4) | 0.0033 (2) | 0.0231 (3) | 0.0232 (2) |
O1A | 0.0269 (6) | 0.0187 (6) | 0.0416 (6) | 0.0025 (5) | 0.0062 (5) | 0.0063 (5) |
N1A | 0.0226 (7) | 0.0181 (6) | 0.0317 (7) | −0.0033 (5) | 0.0048 (5) | 0.0055 (5) |
C1A | 0.0191 (7) | 0.0178 (7) | 0.0305 (8) | 0.0019 (6) | 0.0064 (6) | 0.0073 (6) |
N2A | 0.0224 (7) | 0.0160 (6) | 0.0268 (7) | −0.0012 (5) | 0.0082 (5) | 0.0017 (5) |
C2A | 0.0213 (8) | 0.0226 (8) | 0.0207 (7) | 0.0001 (6) | 0.0036 (6) | 0.0050 (6) |
C3A | 0.0273 (9) | 0.0201 (8) | 0.0470 (10) | −0.0067 (7) | 0.0088 (7) | 0.0067 (7) |
C11A | 0.0217 (8) | 0.0236 (8) | 0.0265 (8) | −0.0044 (6) | 0.0015 (6) | 0.0033 (6) |
C12A | 0.0334 (9) | 0.0238 (8) | 0.0373 (9) | −0.0004 (7) | 0.0046 (7) | 0.0013 (7) |
C13A | 0.0437 (11) | 0.0430 (11) | 0.0361 (10) | −0.0017 (9) | 0.0114 (8) | −0.0075 (8) |
C14A | 0.0498 (12) | 0.0572 (13) | 0.0267 (9) | −0.0098 (10) | 0.0052 (8) | 0.0054 (8) |
C15A | 0.0487 (12) | 0.0448 (11) | 0.0307 (9) | −0.0062 (9) | −0.0004 (8) | 0.0157 (8) |
C16A | 0.0332 (9) | 0.0271 (8) | 0.0314 (8) | −0.0008 (7) | 0.0006 (7) | 0.0069 (7) |
C21A | 0.0213 (8) | 0.0207 (7) | 0.0176 (6) | −0.0010 (6) | 0.0054 (5) | 0.0020 (5) |
C22A | 0.0226 (8) | 0.0241 (8) | 0.0248 (7) | 0.0004 (6) | 0.0081 (6) | 0.0056 (6) |
C23A | 0.0343 (9) | 0.0211 (8) | 0.0294 (8) | −0.0016 (7) | 0.0103 (7) | 0.0067 (6) |
C24A | 0.0302 (9) | 0.0324 (9) | 0.0273 (8) | −0.0124 (7) | 0.0057 (7) | 0.0054 (7) |
C25A | 0.0206 (8) | 0.0383 (9) | 0.0261 (8) | −0.0045 (7) | 0.0026 (6) | 0.0077 (7) |
C26A | 0.0211 (8) | 0.0277 (8) | 0.0222 (7) | 0.0013 (6) | 0.0036 (6) | 0.0045 (6) |
S1B | 0.0313 (2) | 0.0291 (2) | 0.0361 (2) | −0.00013 (17) | 0.01604 (17) | 0.00886 (17) |
Cl1B | 0.0509 (3) | 0.0348 (3) | 0.1191 (5) | 0.0049 (2) | 0.0259 (3) | 0.0410 (3) |
N1B | 0.0233 (7) | 0.0190 (6) | 0.0347 (7) | −0.0043 (5) | 0.0077 (5) | 0.0048 (5) |
C1B | 0.0210 (8) | 0.0179 (7) | 0.0320 (8) | 0.0026 (6) | 0.0060 (6) | 0.0084 (6) |
O2B | 0.0267 (6) | 0.0196 (6) | 0.0447 (7) | 0.0023 (5) | 0.0020 (5) | 0.0050 (5) |
N2B | 0.0221 (7) | 0.0167 (6) | 0.0284 (7) | −0.0009 (5) | 0.0071 (5) | 0.0026 (5) |
C2B | 0.0221 (8) | 0.0230 (8) | 0.0197 (7) | 0.0005 (6) | 0.0031 (6) | 0.0030 (6) |
C3B | 0.0317 (10) | 0.0226 (8) | 0.0553 (11) | −0.0098 (7) | 0.0124 (8) | 0.0042 (8) |
C11B | 0.0235 (8) | 0.0216 (8) | 0.0290 (8) | −0.0055 (6) | 0.0017 (6) | 0.0011 (6) |
C12B | 0.0310 (9) | 0.0249 (8) | 0.0338 (9) | −0.0009 (7) | 0.0015 (7) | 0.0006 (7) |
C13B | 0.0373 (10) | 0.0393 (10) | 0.0310 (9) | −0.0008 (8) | 0.0057 (7) | −0.0060 (8) |
C14B | 0.0493 (12) | 0.0530 (12) | 0.0250 (9) | −0.0081 (9) | 0.0053 (8) | 0.0023 (8) |
C15B | 0.0553 (13) | 0.0454 (11) | 0.0354 (10) | −0.0027 (9) | 0.0000 (9) | 0.0161 (8) |
C16B | 0.0379 (10) | 0.0293 (9) | 0.0352 (9) | 0.0013 (7) | 0.0016 (7) | 0.0070 (7) |
C21B | 0.0208 (7) | 0.0228 (7) | 0.0173 (7) | −0.0007 (6) | 0.0051 (5) | 0.0020 (6) |
C22B | 0.0226 (8) | 0.0260 (8) | 0.0293 (8) | 0.0020 (6) | 0.0089 (6) | 0.0075 (6) |
C23B | 0.0331 (9) | 0.0258 (8) | 0.0393 (9) | −0.0006 (7) | 0.0112 (7) | 0.0120 (7) |
C24B | 0.0295 (9) | 0.0370 (10) | 0.0348 (9) | −0.0102 (7) | 0.0059 (7) | 0.0107 (7) |
C25B | 0.0192 (8) | 0.0437 (10) | 0.0310 (8) | −0.0031 (7) | 0.0015 (6) | 0.0110 (7) |
C26B | 0.0243 (8) | 0.0303 (8) | 0.0244 (7) | 0.0027 (6) | 0.0025 (6) | 0.0062 (6) |
S1—C1 | 1.6799 (16) | C13A—C14A | 1.387 (3) |
Cl1—C23 | 1.7475 (19) | C13A—H13A | 0.9500 |
N1—C1 | 1.3431 (19) | C14A—C15A | 1.391 (3) |
N1—C11 | 1.447 (2) | C14A—H14A | 0.9500 |
N1—C3 | 1.4737 (19) | C15A—C16A | 1.389 (3) |
C1—N2 | 1.4050 (19) | C15A—H15A | 0.9500 |
O2—C2 | 1.2213 (19) | C16A—H16A | 0.9500 |
N2—C2 | 1.387 (2) | C21A—C22A | 1.396 (2) |
N2—H2 | 0.84 (2) | C21A—C26A | 1.403 (2) |
C2—C21 | 1.498 (2) | C22A—C23A | 1.390 (2) |
C3—H3A | 0.9800 | C22A—H22A | 0.9500 |
C3—H3B | 0.9800 | C23A—C24A | 1.389 (2) |
C3—H3C | 0.9800 | C24A—C25A | 1.385 (2) |
C11—C16 | 1.386 (2) | C24A—H24A | 0.9500 |
C11—C12 | 1.397 (2) | C25A—C26A | 1.386 (2) |
C12—C13 | 1.389 (3) | C25A—H25A | 0.9500 |
C12—H12 | 0.9500 | C26A—H26A | 0.9500 |
C13—C14 | 1.389 (3) | S1B—C1B | 1.6758 (16) |
C13—H13 | 0.9500 | Cl1B—C23B | 1.7458 (18) |
C14—C15 | 1.388 (3) | N1B—C1B | 1.338 (2) |
C14—H14 | 0.9500 | N1B—C11B | 1.449 (2) |
C15—C16 | 1.387 (2) | N1B—C3B | 1.4745 (19) |
C15—H15 | 0.9500 | C1B—N2B | 1.4102 (19) |
C16—H16 | 0.9500 | O2B—C2B | 1.2188 (19) |
C21—C22 | 1.394 (2) | N2B—C2B | 1.391 (2) |
C21—C26 | 1.398 (2) | N2B—H2B | 0.82 (2) |
C22—C23 | 1.389 (2) | C2B—C21B | 1.495 (2) |
C22—H22 | 0.9500 | C3B—H3G | 0.9800 |
C23—C24 | 1.384 (3) | C3B—H3H | 0.9800 |
C24—C25 | 1.385 (3) | C3B—H3I | 0.9800 |
C24—H24 | 0.9500 | C11B—C16B | 1.391 (2) |
C25—C26 | 1.385 (2) | C11B—C12B | 1.396 (2) |
C25—H25 | 0.9500 | C12B—C13B | 1.384 (3) |
C26—H26 | 0.9500 | C12B—H12B | 0.9500 |
S1A—C1A | 1.6806 (16) | C13B—C14B | 1.387 (3) |
Cl1A—C23A | 1.7462 (17) | C13B—H13B | 0.9500 |
O1A—C2A | 1.2235 (19) | C14B—C15B | 1.389 (3) |
N1A—C1A | 1.3429 (19) | C14B—H14B | 0.9500 |
N1A—C11A | 1.447 (2) | C15B—C16B | 1.384 (3) |
N1A—C3A | 1.4691 (19) | C15B—H15B | 0.9500 |
C1A—N2A | 1.4075 (19) | C16B—H16B | 0.9500 |
N2A—C2A | 1.387 (2) | C21B—C22B | 1.394 (2) |
N2A—H2A | 0.82 (2) | C21B—C26B | 1.401 (2) |
C2A—C21A | 1.491 (2) | C22B—C23B | 1.389 (2) |
C3A—H3D | 0.9800 | C22B—H22B | 0.9500 |
C3A—H3E | 0.9800 | C23B—C24B | 1.387 (3) |
C3A—H3F | 0.9800 | C24B—C25B | 1.385 (3) |
C11A—C16A | 1.388 (2) | C24B—H24B | 0.9500 |
C11A—C12A | 1.398 (2) | C25B—C26B | 1.389 (2) |
C12A—C13A | 1.391 (3) | C25B—H25B | 0.9500 |
C12A—H12A | 0.9500 | C26B—H26B | 0.9500 |
C1—N1—C11 | 123.55 (13) | C13A—C14A—C15A | 119.95 (18) |
C1—N1—C3 | 118.83 (13) | C13A—C14A—H14A | 120.0 |
C11—N1—C3 | 116.96 (12) | C15A—C14A—H14A | 120.0 |
N1—C1—N2 | 117.29 (13) | C14A—C15A—C16A | 119.92 (18) |
N1—C1—S1 | 123.24 (12) | C14A—C15A—H15A | 120.0 |
N2—C1—S1 | 119.46 (11) | C16A—C15A—H15A | 120.0 |
C2—N2—C1 | 124.13 (13) | C11A—C16A—C15A | 119.90 (17) |
C2—N2—H2 | 117.2 (15) | C11A—C16A—H16A | 120.0 |
C1—N2—H2 | 112.5 (15) | C15A—C16A—H16A | 120.0 |
O2—C2—N2 | 122.80 (14) | C22A—C21A—C26A | 119.91 (14) |
O2—C2—C21 | 122.26 (14) | C22A—C21A—C2A | 122.16 (14) |
N2—C2—C21 | 114.94 (13) | C26A—C21A—C2A | 117.93 (14) |
N1—C3—H3A | 109.5 | C23A—C22A—C21A | 118.86 (15) |
N1—C3—H3B | 109.5 | C23A—C22A—H22A | 120.6 |
H3A—C3—H3B | 109.5 | C21A—C22A—H22A | 120.6 |
N1—C3—H3C | 109.5 | C22A—C23A—C24A | 121.67 (15) |
H3A—C3—H3C | 109.5 | C22A—C23A—Cl1A | 118.69 (13) |
H3B—C3—H3C | 109.5 | C24A—C23A—Cl1A | 119.64 (13) |
C16—C11—C12 | 120.79 (16) | C25A—C24A—C23A | 118.87 (15) |
C16—C11—N1 | 119.68 (14) | C25A—C24A—H24A | 120.6 |
C12—C11—N1 | 119.51 (15) | C23A—C24A—H24A | 120.6 |
C13—C12—C11 | 118.73 (18) | C24A—C25A—C26A | 120.87 (15) |
C13—C12—H12 | 120.6 | C24A—C25A—H25A | 119.6 |
C11—C12—H12 | 120.6 | C26A—C25A—H25A | 119.6 |
C12—C13—C14 | 120.82 (18) | C25A—C26A—C21A | 119.77 (15) |
C12—C13—H13 | 119.6 | C25A—C26A—H26A | 120.1 |
C14—C13—H13 | 119.6 | C21A—C26A—H26A | 120.1 |
C15—C14—C13 | 119.67 (18) | C1B—N1B—C11B | 123.22 (13) |
C15—C14—H14 | 120.2 | C1B—N1B—C3B | 119.87 (14) |
C13—C14—H14 | 120.2 | C11B—N1B—C3B | 116.77 (13) |
C14—C15—C16 | 120.26 (19) | N1B—C1B—N2B | 115.78 (14) |
C14—C15—H15 | 119.9 | N1B—C1B—S1B | 124.16 (12) |
C16—C15—H15 | 119.9 | N2B—C1B—S1B | 120.05 (11) |
C11—C16—C15 | 119.66 (17) | C2B—N2B—C1B | 121.70 (13) |
C11—C16—H16 | 120.2 | C2B—N2B—H2B | 118.5 (15) |
C15—C16—H16 | 120.2 | C1B—N2B—H2B | 113.5 (16) |
C22—C21—C26 | 120.16 (14) | O2B—C2B—N2B | 122.16 (14) |
C22—C21—C2 | 121.78 (14) | O2B—C2B—C21B | 122.42 (14) |
C26—C21—C2 | 118.06 (14) | N2B—C2B—C21B | 115.41 (13) |
C23—C22—C21 | 118.71 (15) | N1B—C3B—H3G | 109.5 |
C23—C22—H22 | 120.6 | N1B—C3B—H3H | 109.5 |
C21—C22—H22 | 120.6 | H3G—C3B—H3H | 109.5 |
C24—C23—C22 | 121.63 (17) | N1B—C3B—H3I | 109.5 |
C24—C23—Cl1 | 119.58 (14) | H3G—C3B—H3I | 109.5 |
C22—C23—Cl1 | 118.79 (14) | H3H—C3B—H3I | 109.5 |
C25—C24—C23 | 119.05 (16) | C16B—C11B—C12B | 120.90 (16) |
C25—C24—H24 | 120.5 | C16B—C11B—N1B | 119.80 (15) |
C23—C24—H24 | 120.5 | C12B—C11B—N1B | 119.28 (15) |
C24—C25—C26 | 120.68 (16) | C13B—C12B—C11B | 118.93 (17) |
C24—C25—H25 | 119.7 | C13B—C12B—H12B | 120.5 |
C26—C25—H25 | 119.7 | C11B—C12B—H12B | 120.5 |
C25—C26—C21 | 119.75 (16) | C12B—C13B—C14B | 120.55 (18) |
C25—C26—H26 | 120.1 | C12B—C13B—H13B | 119.7 |
C21—C26—H26 | 120.1 | C14B—C13B—H13B | 119.7 |
C1A—N1A—C11A | 123.43 (13) | C13B—C14B—C15B | 120.02 (18) |
C1A—N1A—C3A | 119.17 (13) | C13B—C14B—H14B | 120.0 |
C11A—N1A—C3A | 117.03 (12) | C15B—C14B—H14B | 120.0 |
N1A—C1A—N2A | 116.77 (13) | C16B—C15B—C14B | 120.28 (19) |
N1A—C1A—S1A | 123.86 (12) | C16B—C15B—H15B | 119.9 |
N2A—C1A—S1A | 119.37 (11) | C14B—C15B—H15B | 119.9 |
C2A—N2A—C1A | 123.70 (13) | C15B—C16B—C11B | 119.29 (18) |
C2A—N2A—H2A | 116.8 (14) | C15B—C16B—H16B | 120.4 |
C1A—N2A—H2A | 115.4 (15) | C11B—C16B—H16B | 120.4 |
O1A—C2A—N2A | 122.44 (14) | C22B—C21B—C26B | 120.26 (14) |
O1A—C2A—C21A | 122.32 (14) | C22B—C21B—C2B | 122.23 (14) |
N2A—C2A—C21A | 115.24 (13) | C26B—C21B—C2B | 117.50 (14) |
N1A—C3A—H3D | 109.5 | C23B—C22B—C21B | 118.52 (15) |
N1A—C3A—H3E | 109.5 | C23B—C22B—H22B | 120.7 |
H3D—C3A—H3E | 109.5 | C21B—C22B—H22B | 120.7 |
N1A—C3A—H3F | 109.5 | C22B—C23B—C24B | 121.99 (16) |
H3D—C3A—H3F | 109.5 | C22B—C23B—Cl1B | 118.56 (13) |
H3E—C3A—H3F | 109.5 | C24B—C23B—Cl1B | 119.45 (13) |
C16A—C11A—C12A | 120.53 (16) | C25B—C24B—C23B | 118.82 (16) |
C16A—C11A—N1A | 119.87 (14) | C25B—C24B—H24B | 120.6 |
C12A—C11A—N1A | 119.58 (15) | C23B—C24B—H24B | 120.6 |
C13A—C12A—C11A | 118.90 (18) | C24B—C25B—C26B | 120.73 (15) |
C13A—C12A—H12A | 120.6 | C24B—C25B—H25B | 119.6 |
C11A—C12A—H12A | 120.6 | C26B—C25B—H25B | 119.6 |
C14A—C13A—C12A | 120.71 (18) | C25B—C26B—C21B | 119.66 (15) |
C14A—C13A—H13A | 119.6 | C25B—C26B—H26B | 120.2 |
C12A—C13A—H13A | 119.6 | C21B—C26B—H26B | 120.2 |
C11—N1—C1—N2 | −12.0 (2) | C12A—C11A—C16A—C15A | −3.2 (2) |
C3—N1—C1—N2 | 177.57 (13) | N1A—C11A—C16A—C15A | 178.25 (15) |
C11—N1—C1—S1 | 167.06 (12) | C14A—C15A—C16A—C11A | 2.1 (3) |
C3—N1—C1—S1 | −3.4 (2) | O1A—C2A—C21A—C22A | 156.62 (15) |
N1—C1—N2—C2 | −54.6 (2) | N2A—C2A—C21A—C22A | −23.4 (2) |
S1—C1—N2—C2 | 126.24 (14) | O1A—C2A—C21A—C26A | −22.9 (2) |
C1—N2—C2—O2 | 0.3 (2) | N2A—C2A—C21A—C26A | 157.03 (13) |
C1—N2—C2—C21 | −178.95 (13) | C26A—C21A—C22A—C23A | −2.3 (2) |
C1—N1—C11—C16 | −52.5 (2) | C2A—C21A—C22A—C23A | 178.10 (13) |
C3—N1—C11—C16 | 118.05 (16) | C21A—C22A—C23A—C24A | 1.7 (2) |
C1—N1—C11—C12 | 129.13 (16) | C21A—C22A—C23A—Cl1A | −177.80 (11) |
C3—N1—C11—C12 | −60.3 (2) | C22A—C23A—C24A—C25A | 0.3 (2) |
C16—C11—C12—C13 | 1.2 (2) | Cl1A—C23A—C24A—C25A | 179.84 (12) |
N1—C11—C12—C13 | 179.48 (15) | C23A—C24A—C25A—C26A | −1.8 (2) |
C11—C12—C13—C14 | 1.4 (3) | C24A—C25A—C26A—C21A | 1.1 (2) |
C12—C13—C14—C15 | −2.5 (3) | C22A—C21A—C26A—C25A | 0.9 (2) |
C13—C14—C15—C16 | 0.9 (3) | C2A—C21A—C26A—C25A | −179.48 (13) |
C12—C11—C16—C15 | −2.7 (2) | C11B—N1B—C1B—N2B | −7.2 (2) |
N1—C11—C16—C15 | 178.99 (15) | C3B—N1B—C1B—N2B | 177.22 (14) |
C14—C15—C16—C11 | 1.6 (3) | C11B—N1B—C1B—S1B | 172.21 (12) |
O2—C2—C21—C22 | 153.84 (15) | C3B—N1B—C1B—S1B | −3.4 (2) |
N2—C2—C21—C22 | −26.9 (2) | N1B—C1B—N2B—C2B | −62.64 (19) |
O2—C2—C21—C26 | −25.9 (2) | S1B—C1B—N2B—C2B | 117.92 (14) |
N2—C2—C21—C26 | 153.39 (13) | C1B—N2B—C2B—O2B | 1.3 (2) |
C26—C21—C22—C23 | −1.3 (2) | C1B—N2B—C2B—C21B | −179.49 (13) |
C2—C21—C22—C23 | 178.97 (14) | C1B—N1B—C11B—C16B | −61.9 (2) |
C21—C22—C23—C24 | 0.8 (3) | C3B—N1B—C11B—C16B | 113.79 (17) |
C21—C22—C23—Cl1 | −179.10 (12) | C1B—N1B—C11B—C12B | 119.62 (17) |
C22—C23—C24—C25 | 0.2 (3) | C3B—N1B—C11B—C12B | −64.7 (2) |
Cl1—C23—C24—C25 | −179.93 (13) | C16B—C11B—C12B—C13B | 2.4 (2) |
C23—C24—C25—C26 | −0.6 (3) | N1B—C11B—C12B—C13B | −179.20 (14) |
C24—C25—C26—C21 | 0.0 (2) | C11B—C12B—C13B—C14B | −0.9 (2) |
C22—C21—C26—C25 | 1.0 (2) | C12B—C13B—C14B—C15B | −0.7 (3) |
C2—C21—C26—C25 | −179.34 (14) | C13B—C14B—C15B—C16B | 0.8 (3) |
C11A—N1A—C1A—N2A | −11.8 (2) | C14B—C15B—C16B—C11B | 0.7 (3) |
C3A—N1A—C1A—N2A | 175.44 (13) | C12B—C11B—C16B—C15B | −2.3 (2) |
C11A—N1A—C1A—S1A | 167.80 (12) | N1B—C11B—C16B—C15B | 179.27 (15) |
C3A—N1A—C1A—S1A | −5.0 (2) | O2B—C2B—C21B—C22B | 161.20 (14) |
N1A—C1A—N2A—C2A | −56.6 (2) | N2B—C2B—C21B—C22B | −18.0 (2) |
S1A—C1A—N2A—C2A | 123.84 (14) | O2B—C2B—C21B—C26B | −17.7 (2) |
C1A—N2A—C2A—O1A | 1.3 (2) | N2B—C2B—C21B—C26B | 163.15 (13) |
C1A—N2A—C2A—C21A | −178.70 (13) | C26B—C21B—C22B—C23B | −1.5 (2) |
C1A—N1A—C11A—C16A | −50.7 (2) | C2B—C21B—C22B—C23B | 179.63 (14) |
C3A—N1A—C11A—C16A | 122.18 (16) | C21B—C22B—C23B—C24B | 1.0 (2) |
C1A—N1A—C11A—C12A | 130.74 (16) | C21B—C22B—C23B—Cl1B | −179.17 (12) |
C3A—N1A—C11A—C12A | −56.3 (2) | C22B—C23B—C24B—C25B | 0.4 (3) |
C16A—C11A—C12A—C13A | 1.5 (2) | Cl1B—C23B—C24B—C25B | −179.43 (13) |
N1A—C11A—C12A—C13A | −179.96 (15) | C23B—C24B—C25B—C26B | −1.3 (3) |
C11A—C12A—C13A—C14A | 1.4 (3) | C24B—C25B—C26B—C21B | 0.7 (2) |
C12A—C13A—C14A—C15A | −2.5 (3) | C22B—C21B—C26B—C25B | 0.7 (2) |
C13A—C14A—C15A—C16A | 0.8 (3) | C2B—C21B—C26B—C25B | 179.60 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···S1i | 0.84 (2) | 2.60 (2) | 3.4293 (14) | 172.1 (19) |
N2A—H2A···S1Bii | 0.82 (2) | 2.76 (2) | 3.5776 (14) | 171.6 (18) |
N2B—H2B···S1Aii | 0.82 (2) | 2.76 (2) | 3.5765 (14) | 174 (2) |
Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) −x+1, −y+1, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register