Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806055048/sj2200sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806055048/sj2200Isup2.hkl |
CCDC reference: 638527
Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus; program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTO (Meetsma, 2006) and PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
C15H16N2S | F(000) = 1088 |
Mr = 256.37 | The final unit cell was obtained from the xyz centroids of
6808 reflections after integration using the SAINTPLUS
software package (Bruker, 2000). Reduced cell calculations did not indicate any higher metric lattice symmetry and examination of the final atomic coordinates of the structure did not yield extra symmetry elements (Spek, 1988; Le Page 1987, 1988) |
Monoclinic, P21/n | Dx = 1.241 Mg m−3 |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 12.3960 (9) Å | Cell parameters from 6808 reflections |
b = 9.5652 (7) Å | θ = 2.3–29.1° |
c = 23.163 (2) Å | µ = 0.22 mm−1 |
β = 92.266 (1)° | T = 100 K |
V = 2744.3 (4) Å3 | Block, colourless |
Z = 8 | 0.49 × 0.23 × 0.16 mm |
Bruker SMART APEX CCD area-detector diffractometer | 6776 independent reflections |
Radiation source: fine focus sealed Siemens Mo tube | 5577 reflections with I > 2σ(I) |
Parallel mounted graphite monochromator | Rint = 0.034 |
Detector resolution: 4096x4096/62x62 (binned 512) pixels mm-1 | θmax = 28.3°, θmin = 2.7° |
φ and ω scans | h = −16→16 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −12→12 |
Tmin = 0.886, Tmax = 0.966 | l = −30→29 |
22738 measured reflections |
Refinement on F2 | Primary atom site location: heavy-atom method |
Least-squares matrix: full | Secondary atom site location: structure-invariant direct methods |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.105 | All H-atom parameters refined |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0424P)2 + 1.5124P] where P = (Fo2 + 2Fc2)/3 |
6776 reflections | (Δ/σ)max = 0.001 |
453 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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 | 0.47963 (3) | 0.74484 (4) | 0.15212 (2) | 0.0185 (1) | |
N11 | 0.64627 (11) | 0.58167 (15) | 0.12974 (6) | 0.0195 (4) | |
N12 | 0.47770 (11) | 0.48848 (14) | 0.10861 (6) | 0.0172 (4) | |
C11 | 0.71217 (17) | 0.7660 (2) | 0.04043 (9) | 0.0329 (6) | |
C12 | 0.75265 (13) | 0.78441 (18) | 0.10166 (8) | 0.0251 (5) | |
C13 | 0.82468 (15) | 0.8907 (2) | 0.11825 (10) | 0.0332 (6) | |
C14 | 0.86198 (15) | 0.9059 (2) | 0.17500 (11) | 0.0376 (7) | |
C15 | 0.82852 (15) | 0.8145 (2) | 0.21703 (10) | 0.0354 (7) | |
C16 | 0.75686 (14) | 0.7065 (2) | 0.20185 (9) | 0.0269 (5) | |
C17 | 0.71958 (12) | 0.69366 (17) | 0.14507 (8) | 0.0206 (5) | |
C18 | 0.41792 (16) | 0.2230 (2) | 0.15657 (8) | 0.0261 (6) | |
C19 | 0.48845 (13) | 0.23336 (17) | 0.10525 (7) | 0.0191 (5) | |
C110 | 0.52634 (14) | 0.11385 (18) | 0.07810 (8) | 0.0248 (5) | |
C111 | 0.58774 (14) | 0.12300 (19) | 0.02944 (8) | 0.0262 (5) | |
C112 | 0.61274 (13) | 0.25207 (19) | 0.00640 (8) | 0.0218 (5) | |
C113 | 0.57748 (13) | 0.37261 (17) | 0.03319 (7) | 0.0182 (4) | |
C114 | 0.51644 (12) | 0.36341 (16) | 0.08239 (7) | 0.0156 (4) | |
C115 | 0.53793 (12) | 0.59647 (16) | 0.12843 (7) | 0.0157 (4) | |
H11 | 0.7434 (19) | 0.841 (3) | 0.0147 (10) | 0.045 (7)* | |
H11' | 0.7317 (19) | 0.670 (3) | 0.0261 (10) | 0.050 (7)* | |
H11'' | 0.631 (2) | 0.775 (2) | 0.0386 (10) | 0.045 (7)* | |
H13 | 0.8476 (17) | 0.956 (2) | 0.0878 (9) | 0.035 (6)* | |
H14 | 0.9114 (18) | 0.978 (2) | 0.1856 (10) | 0.042 (6)* | |
H15 | 0.8510 (18) | 0.820 (2) | 0.2553 (10) | 0.036 (6)* | |
H16 | 0.7343 (13) | 0.6321 (17) | 0.2313 (7) | 0.006 (4)* | |
H18 | 0.4460 (18) | 0.276 (2) | 0.1883 (10) | 0.038 (6)* | |
H18' | 0.4079 (18) | 0.127 (3) | 0.1680 (10) | 0.044 (6)* | |
H18'' | 0.344 (2) | 0.261 (2) | 0.1473 (10) | 0.046 (7)* | |
H110 | 0.5075 (16) | 0.025 (2) | 0.0937 (9) | 0.029 (5)* | |
H111 | 0.6107 (17) | 0.039 (2) | 0.0118 (9) | 0.035 (6)* | |
H112 | 0.6531 (16) | 0.261 (2) | −0.0273 (9) | 0.025 (5)* | |
H113 | 0.5935 (15) | 0.463 (2) | 0.0182 (8) | 0.018 (5)* | |
H121 | 0.6717 (16) | 0.506 (2) | 0.1170 (8) | 0.026 (5)* | |
H122 | 0.4078 (18) | 0.497 (2) | 0.1109 (9) | 0.030 (5)* | |
S2 | 0.20838 (3) | 0.48035 (4) | 0.09584 (2) | 0.0194 (1) | |
N21 | 0.04656 (11) | 0.64940 (15) | 0.12219 (6) | 0.0189 (4) | |
N22 | 0.21681 (11) | 0.74524 (14) | 0.12945 (6) | 0.0173 (4) | |
C21 | 0.00271 (17) | 0.4945 (2) | 0.22449 (8) | 0.0285 (6) | |
C22 | −0.04967 (13) | 0.45726 (17) | 0.16709 (7) | 0.0187 (5) | |
C23 | −0.12127 (14) | 0.34519 (18) | 0.16081 (8) | 0.0223 (5) | |
C24 | −0.16923 (13) | 0.31106 (18) | 0.10754 (8) | 0.0232 (5) | |
C25 | −0.14683 (13) | 0.39005 (19) | 0.05912 (8) | 0.0226 (5) | |
C26 | −0.07660 (13) | 0.50254 (18) | 0.06428 (7) | 0.0191 (4) | |
C27 | −0.02766 (12) | 0.53382 (16) | 0.11744 (7) | 0.0168 (4) | |
C28 | 0.12245 (17) | 0.9518 (2) | 0.05150 (8) | 0.0294 (6) | |
C29 | 0.13615 (13) | 0.97793 (17) | 0.11524 (7) | 0.0201 (5) | |
C210 | 0.10626 (14) | 1.10519 (18) | 0.13975 (8) | 0.0246 (5) | |
C211 | 0.11820 (14) | 1.12838 (19) | 0.19848 (9) | 0.0268 (5) | |
C212 | 0.16143 (15) | 1.0259 (2) | 0.23491 (8) | 0.0271 (5) | |
C213 | 0.19259 (14) | 0.89874 (18) | 0.21176 (8) | 0.0219 (5) | |
C214 | 0.17978 (12) | 0.87550 (16) | 0.15252 (7) | 0.0173 (4) | |
C215 | 0.15426 (12) | 0.63346 (16) | 0.11717 (7) | 0.0156 (4) | |
H21 | 0.0813 (18) | 0.483 (2) | 0.2220 (9) | 0.031 (5)* | |
H21' | −0.0161 (18) | 0.592 (2) | 0.2346 (9) | 0.039 (6)* | |
H21'' | −0.0213 (19) | 0.436 (3) | 0.2537 (11) | 0.048 (7)* | |
H23 | −0.1361 (16) | 0.294 (2) | 0.1947 (9) | 0.028 (5)* | |
H24 | −0.2176 (16) | 0.233 (2) | 0.1047 (8) | 0.025 (5)* | |
H25 | −0.1780 (15) | 0.368 (2) | 0.0229 (8) | 0.022 (5)* | |
H26 | −0.0607 (15) | 0.561 (2) | 0.0327 (8) | 0.019 (5)* | |
H28 | 0.1000 (19) | 1.042 (3) | 0.0345 (10) | 0.045 (6)* | |
H28' | 0.191 (2) | 0.927 (2) | 0.0344 (10) | 0.044 (6)* | |
H28'' | 0.072 (2) | 0.874 (3) | 0.0435 (10) | 0.054 (7)* | |
H210 | 0.0801 (15) | 1.179 (2) | 0.1144 (8) | 0.025 (5)* | |
H211 | 0.0980 (17) | 1.218 (2) | 0.2137 (9) | 0.031 (5)* | |
H212 | 0.1672 (17) | 1.040 (2) | 0.2753 (10) | 0.033 (6)* | |
H213 | 0.2218 (15) | 0.826 (2) | 0.2360 (8) | 0.020 (5)* | |
H221 | 0.0255 (17) | 0.722 (2) | 0.1378 (9) | 0.027 (5)* | |
H222 | 0.2861 (18) | 0.732 (2) | 0.1322 (9) | 0.028 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0141 (2) | 0.0142 (2) | 0.0274 (2) | 0.0011 (2) | 0.0030 (2) | −0.0055 (2) |
N11 | 0.0142 (7) | 0.0135 (7) | 0.0309 (8) | 0.0013 (5) | 0.0010 (5) | −0.0063 (6) |
N12 | 0.0125 (7) | 0.0141 (6) | 0.0251 (7) | 0.0008 (5) | 0.0030 (5) | −0.0033 (5) |
C11 | 0.0311 (11) | 0.0268 (10) | 0.0412 (12) | 0.0026 (8) | 0.0054 (9) | 0.0078 (9) |
C12 | 0.0151 (8) | 0.0172 (8) | 0.0433 (11) | 0.0030 (6) | 0.0056 (7) | −0.0027 (7) |
C13 | 0.0192 (9) | 0.0231 (9) | 0.0579 (14) | −0.0026 (8) | 0.0104 (9) | −0.0044 (9) |
C14 | 0.0170 (9) | 0.0274 (10) | 0.0690 (15) | −0.0060 (8) | 0.0076 (9) | −0.0195 (10) |
C15 | 0.0212 (9) | 0.0395 (12) | 0.0453 (13) | 0.0009 (8) | −0.0019 (8) | −0.0207 (10) |
C16 | 0.0167 (8) | 0.0266 (9) | 0.0375 (10) | 0.0014 (7) | 0.0027 (7) | −0.0098 (8) |
C17 | 0.0098 (7) | 0.0160 (8) | 0.0362 (10) | 0.0009 (6) | 0.0037 (6) | −0.0083 (7) |
C18 | 0.0280 (10) | 0.0235 (9) | 0.0267 (10) | −0.0027 (8) | 0.0012 (7) | 0.0081 (7) |
C19 | 0.0170 (8) | 0.0172 (8) | 0.0227 (8) | −0.0014 (6) | −0.0042 (6) | 0.0012 (6) |
C110 | 0.0239 (9) | 0.0130 (8) | 0.0370 (10) | −0.0007 (7) | −0.0046 (7) | −0.0002 (7) |
C111 | 0.0214 (9) | 0.0189 (9) | 0.0379 (10) | 0.0028 (7) | −0.0045 (7) | −0.0127 (7) |
C112 | 0.0150 (8) | 0.0264 (9) | 0.0237 (9) | 0.0021 (7) | −0.0021 (6) | −0.0076 (7) |
C113 | 0.0141 (7) | 0.0174 (8) | 0.0229 (8) | 0.0008 (6) | −0.0023 (6) | −0.0009 (6) |
C114 | 0.0124 (7) | 0.0136 (7) | 0.0205 (8) | 0.0016 (6) | −0.0033 (6) | −0.0029 (6) |
C115 | 0.0162 (7) | 0.0139 (7) | 0.0172 (8) | 0.0005 (6) | 0.0021 (6) | 0.0006 (6) |
S2 | 0.0139 (2) | 0.0152 (2) | 0.0290 (2) | 0.0023 (2) | 0.0009 (2) | −0.0055 (2) |
N21 | 0.0141 (7) | 0.0131 (7) | 0.0295 (8) | 0.0010 (5) | 0.0028 (5) | −0.0041 (6) |
N22 | 0.0110 (6) | 0.0142 (6) | 0.0266 (7) | 0.0020 (5) | 0.0015 (5) | −0.0019 (5) |
C21 | 0.0359 (11) | 0.0261 (10) | 0.0229 (9) | 0.0043 (8) | −0.0061 (8) | 0.0016 (7) |
C22 | 0.0167 (8) | 0.0173 (8) | 0.0220 (8) | 0.0050 (6) | 0.0001 (6) | −0.0005 (6) |
C23 | 0.0197 (8) | 0.0191 (8) | 0.0285 (9) | 0.0036 (7) | 0.0057 (7) | 0.0051 (7) |
C24 | 0.0134 (8) | 0.0177 (8) | 0.0386 (10) | −0.0002 (7) | 0.0014 (7) | −0.0034 (7) |
C25 | 0.0155 (8) | 0.0273 (9) | 0.0249 (9) | 0.0022 (7) | −0.0014 (7) | −0.0072 (7) |
C26 | 0.0142 (7) | 0.0225 (8) | 0.0208 (8) | 0.0030 (6) | 0.0039 (6) | 0.0013 (7) |
C27 | 0.0118 (7) | 0.0152 (7) | 0.0235 (8) | 0.0017 (6) | 0.0016 (6) | −0.0014 (6) |
C28 | 0.0319 (10) | 0.0313 (10) | 0.0251 (10) | 0.0074 (9) | 0.0024 (8) | 0.0062 (8) |
C29 | 0.0140 (7) | 0.0195 (8) | 0.0271 (9) | 0.0002 (6) | 0.0033 (6) | 0.0019 (7) |
C210 | 0.0179 (8) | 0.0157 (8) | 0.0403 (11) | 0.0008 (7) | 0.0027 (7) | 0.0037 (7) |
C211 | 0.0187 (8) | 0.0178 (8) | 0.0440 (11) | −0.0001 (7) | 0.0009 (7) | −0.0084 (8) |
C212 | 0.0253 (9) | 0.0274 (9) | 0.0284 (10) | 0.0004 (8) | −0.0002 (7) | −0.0093 (8) |
C213 | 0.0193 (8) | 0.0199 (8) | 0.0264 (9) | 0.0009 (7) | −0.0009 (7) | −0.0011 (7) |
C214 | 0.0115 (7) | 0.0139 (7) | 0.0267 (9) | −0.0008 (6) | 0.0038 (6) | −0.0009 (6) |
C215 | 0.0156 (7) | 0.0151 (7) | 0.0162 (8) | 0.0019 (6) | 0.0007 (6) | 0.0018 (6) |
S1—C115 | 1.6938 (16) | C18—H18 | 0.95 (2) |
S2—C215 | 1.6927 (16) | C18—H18' | 0.97 (3) |
N11—C115 | 1.350 (2) | C18—H18'' | 1.00 (2) |
N11—C17 | 1.440 (2) | C110—H110 | 0.96 (2) |
N12—C114 | 1.433 (2) | C111—H111 | 0.95 (2) |
N12—C115 | 1.345 (2) | C112—H112 | 0.95 (2) |
N11—H121 | 0.847 (19) | C113—H113 | 0.956 (19) |
N12—H122 | 0.87 (2) | C21—C22 | 1.499 (2) |
N21—C27 | 1.440 (2) | C22—C27 | 1.399 (2) |
N21—C215 | 1.353 (2) | C22—C23 | 1.396 (2) |
N22—C215 | 1.345 (2) | C23—C24 | 1.387 (3) |
N22—C214 | 1.438 (2) | C24—C25 | 1.389 (3) |
N21—H221 | 0.83 (2) | C25—C26 | 1.386 (2) |
N22—H222 | 0.87 (2) | C26—C27 | 1.384 (2) |
C11—C12 | 1.496 (3) | C28—C29 | 1.500 (2) |
C12—C17 | 1.402 (2) | C29—C210 | 1.399 (2) |
C12—C13 | 1.397 (3) | C29—C214 | 1.400 (2) |
C13—C14 | 1.384 (3) | C21—H21 | 0.98 (2) |
C14—C15 | 1.384 (3) | C21—H21' | 0.99 (2) |
C15—C16 | 1.398 (3) | C21—H21'' | 0.94 (3) |
C16—C17 | 1.382 (3) | C23—H23 | 0.95 (2) |
C18—C19 | 1.507 (3) | C24—H24 | 0.958 (19) |
C19—C110 | 1.395 (2) | C25—H25 | 0.934 (19) |
C19—C114 | 1.401 (2) | C26—H26 | 0.948 (19) |
C110—C111 | 1.388 (3) | C28—H28' | 0.98 (2) |
C11—H11' | 1.01 (3) | C28—H28'' | 0.99 (3) |
C11—H11'' | 1.01 (2) | C28—H28 | 0.98 (3) |
C111—C112 | 1.385 (3) | C210—C211 | 1.381 (3) |
C11—H11 | 1.02 (3) | C211—C212 | 1.387 (3) |
C112—C113 | 1.388 (2) | C212—C213 | 1.390 (3) |
C113—C114 | 1.395 (2) | C213—C214 | 1.393 (2) |
C13—H13 | 0.99 (2) | C210—H210 | 0.966 (19) |
C14—H14 | 0.95 (2) | C211—H211 | 0.96 (2) |
C15—H15 | 0.92 (2) | C212—H212 | 0.95 (2) |
C16—H16 | 1.032 (16) | C213—H213 | 0.956 (19) |
S1···N22 | 3.2794 (14) | C215···C28 | 3.420 (2) |
S1···C12 | 3.6436 (17) | C210···H14vii | 2.94 (2) |
S1···C16 | 3.5997 (18) | C211···H213ii | 3.094 (19) |
S2···C26 | 3.5853 (17) | C211···H14vii | 2.94 (2) |
S2···N12 | 3.3408 (14) | C214···H221 | 2.42 (2) |
S2···C22 | 3.6636 (17) | C215···H21 | 2.99 (2) |
S1···H110i | 3.03 (2) | C215···H28'' | 3.02 (3) |
S1···H222 | 2.43 (2) | H11···H13 | 2.36 (3) |
S1···H21''ii | 2.88 (3) | H11···H111i | 2.51 (3) |
S1···H212iii | 3.20 (2) | H11···H28x | 2.55 (3) |
S2···H18'' | 2.91 (2) | H11···C28x | 3.04 (3) |
S2···H122 | 2.49 (2) | H11'···N11 | 2.79 (2) |
S2···H25iv | 3.119 (19) | H11'···C26vi | 2.97 (3) |
N11···C113 | 3.095 (2) | H11''···N11 | 2.81 (2) |
N12···S2 | 3.3408 (14) | H11''···C115 | 2.96 (2) |
N21···C29 | 3.339 (2) | H13···H11 | 2.36 (3) |
N22···S1 | 3.2794 (14) | H14···C210vi | 2.94 (2) |
N11···H113 | 2.874 (19) | H14···C211vi | 2.94 (2) |
N11···H11' | 2.79 (2) | H18···N12 | 2.78 (2) |
N11···H11'' | 2.81 (2) | H18'···H110 | 2.37 (3) |
N12···H18'' | 2.90 (2) | H18'···C21iii | 2.97 (2) |
N12···H18 | 2.78 (2) | H18''···S2 | 2.91 (2) |
N21···H21' | 2.80 (2) | H18''···N12 | 2.90 (2) |
N21···H28'' | 2.84 (3) | H18''···H122 | 2.55 (3) |
N21···H21 | 2.83 (2) | H21···N21 | 2.83 (2) |
N22···H28' | 2.81 (2) | H21···C215 | 2.99 (2) |
N22···H28'' | 2.90 (2) | H21···H211ix | 2.55 (3) |
N22···H112v | 2.92 (2) | H21'···C16vii | 3.09 (2) |
C11···C115 | 3.435 (3) | H21'···C18ii | 3.03 (2) |
C12···S1 | 3.6436 (17) | H21'···N21 | 2.80 (2) |
C12···C26vi | 3.556 (2) | H21'···C15vii | 2.89 (2) |
C16···C22vi | 3.498 (2) | H21''···H23 | 2.36 (3) |
C16···S1 | 3.5997 (18) | H21''···S1iii | 2.88 (3) |
C17···C27vi | 3.567 (2) | H23···H21'' | 2.36 (3) |
C21···C215 | 3.442 (3) | H23···C16iii | 2.99 (2) |
C22···C16vii | 3.498 (2) | H24···C112vii | 3.043 (19) |
C22···S2 | 3.6636 (17) | H25···H112vii | 2.57 (3) |
C24···C112vii | 3.551 (2) | H25···C113vii | 3.050 (19) |
C24···C113vii | 3.570 (2) | H25···C112vii | 2.833 (19) |
C25···C112vii | 3.439 (2) | H25···S2iv | 3.119 (19) |
C25···C113vii | 3.450 (2) | H26···C26iv | 2.935 (19) |
C26···C12vii | 3.556 (2) | H26···H26iv | 2.47 (3) |
C26···C26iv | 3.595 (2) | H28···H210 | 2.29 (3) |
C26···S2 | 3.5853 (17) | H28···H11x | 2.55 (3) |
C27···C17vii | 3.567 (2) | H28'···N22 | 2.81 (2) |
C28···C215 | 3.420 (2) | H28''···N21 | 2.84 (3) |
C29···N21 | 3.339 (2) | H28''···N22 | 2.90 (2) |
C11···H111i | 2.96 (2) | H28''···C215 | 3.02 (3) |
C111···C111viii | 3.449 (3) | H110···S1ix | 3.03 (2) |
C112···C25vi | 3.439 (2) | H110···H18' | 2.37 (3) |
C112···C24vi | 3.551 (2) | H111···C11ix | 2.96 (2) |
C113···C24vi | 3.570 (2) | H111···C111viii | 3.03 (2) |
C113···C113v | 3.429 (2) | H111···H11ix | 2.51 (3) |
C113···N11 | 3.095 (2) | H111···C110viii | 3.01 (2) |
C113···C25vi | 3.450 (2) | H112···H25vi | 2.57 (3) |
C13···H221vi | 2.99 (2) | H112···H222v | 2.57 (3) |
C14···H221vi | 2.84 (2) | H112···N22v | 2.92 (2) |
C115···C11 | 3.435 (3) | H113···N11 | 2.874 (19) |
C15···H21'vi | 2.89 (2) | H113···H113v | 2.54 (3) |
C16···H21'vi | 3.09 (2) | H113···C113v | 2.860 (19) |
C16···H23ii | 2.99 (2) | H113···C115 | 2.960 (19) |
C18···H21'iii | 3.03 (2) | H113···H121 | 2.48 (3) |
C18···H122 | 2.827 (19) | H121···C24vi | 2.73 (2) |
C21···H18'ii | 2.97 (2) | H121···C114 | 2.47 (2) |
C21···H211ix | 2.91 (2) | H121···C25vi | 2.89 (2) |
C21···H221 | 2.98 (2) | H121···C113 | 2.565 (19) |
C22···H211ix | 3.10 (2) | H121···H113 | 2.48 (3) |
C24···H121vii | 2.73 (2) | H122···H18'' | 2.55 (3) |
C25···H121vii | 2.89 (2) | H122···S2 | 2.49 (2) |
C26···H11'vii | 2.97 (3) | H122···C18 | 2.827 (19) |
C26···H26iv | 2.935 (19) | H210···H28 | 2.29 (3) |
C28···H11x | 3.04 (3) | H211···C21i | 2.91 (2) |
C29···H221 | 2.86 (2) | H211···C22i | 3.10 (2) |
C110···H111viii | 3.01 (2) | H211···H21i | 2.55 (3) |
C111···H111viii | 3.03 (2) | H212···S1ii | 3.20 (2) |
C112···H24vi | 3.043 (19) | H213···C211iii | 3.094 (19) |
C112···H25vi | 2.833 (19) | H221···C13vii | 2.99 (2) |
C113···H121 | 2.565 (19) | H221···C14vii | 2.84 (2) |
C113···H25vi | 3.050 (19) | H221···C21 | 2.98 (2) |
C113···H113v | 2.860 (19) | H221···C29 | 2.86 (2) |
C114···H121 | 2.47 (2) | H221···C214 | 2.42 (2) |
C115···H113 | 2.960 (19) | H222···S1 | 2.43 (2) |
C115···H11'' | 2.96 (2) | H222···H112v | 2.57 (3) |
C215···C21 | 3.442 (3) | ||
C17—N11—C115 | 123.04 (14) | C112—C111—H111 | 120.9 (13) |
C114—N12—C115 | 126.52 (13) | C110—C111—H111 | 118.6 (13) |
C17—N11—H121 | 118.8 (13) | C111—C112—H112 | 122.1 (12) |
C115—N11—H121 | 117.7 (13) | C113—C112—H112 | 118.6 (12) |
C114—N12—H122 | 117.0 (13) | C114—C113—H113 | 118.8 (11) |
C115—N12—H122 | 116.5 (13) | C112—C113—H113 | 121.0 (11) |
C27—N21—C215 | 122.45 (14) | C21—C22—C23 | 121.75 (15) |
C214—N22—C215 | 125.29 (13) | C21—C22—C27 | 120.85 (15) |
C27—N21—H221 | 117.7 (14) | C23—C22—C27 | 117.40 (15) |
C215—N21—H221 | 117.4 (15) | C22—C23—C24 | 121.46 (16) |
C215—N22—H222 | 117.4 (13) | C23—C24—C25 | 119.85 (16) |
C214—N22—H222 | 115.4 (13) | C24—C25—C26 | 119.83 (16) |
C11—C12—C17 | 120.70 (16) | C25—C26—C27 | 119.76 (15) |
C11—C12—C13 | 122.23 (17) | N21—C27—C22 | 118.94 (14) |
C13—C12—C17 | 117.08 (17) | N21—C27—C26 | 119.37 (14) |
C12—C13—C14 | 121.58 (19) | C22—C27—C26 | 121.69 (15) |
C13—C14—C15 | 120.24 (18) | C210—C29—C214 | 117.42 (15) |
C14—C15—C16 | 119.7 (2) | C28—C29—C210 | 121.51 (15) |
C15—C16—C17 | 119.35 (18) | C28—C29—C214 | 121.07 (15) |
C12—C17—C16 | 122.09 (16) | C22—C21—H21'' | 111.1 (16) |
N11—C17—C12 | 118.90 (16) | H21—C21—H21' | 111.2 (17) |
N11—C17—C16 | 118.99 (15) | C22—C21—H21' | 109.6 (12) |
C18—C19—C114 | 121.12 (15) | C22—C21—H21 | 108.5 (12) |
C110—C19—C114 | 117.67 (15) | H21'—C21—H21'' | 108 (2) |
C18—C19—C110 | 121.20 (15) | H21—C21—H21'' | 108.6 (19) |
C19—C110—C111 | 121.32 (16) | C22—C23—H23 | 116.9 (12) |
C110—C111—C112 | 120.50 (17) | C24—C23—H23 | 121.6 (12) |
C12—C11—H11'' | 109.0 (13) | C25—C24—H24 | 120.9 (11) |
H11—C11—H11'' | 108.5 (18) | C23—C24—H24 | 119.3 (11) |
H11—C11—H11' | 110 (2) | C24—C25—H25 | 120.9 (12) |
C12—C11—H11 | 110.5 (14) | C26—C25—H25 | 119.3 (12) |
H11'—C11—H11'' | 108.4 (18) | C25—C26—H26 | 122.7 (11) |
C12—C11—H11' | 110.1 (14) | C27—C26—H26 | 117.5 (11) |
C111—C112—C113 | 119.27 (16) | H28—C28—H28' | 106.6 (18) |
C112—C113—C114 | 120.21 (15) | H28—C28—H28'' | 115 (2) |
C14—C13—H13 | 121.0 (12) | H28'—C28—H28'' | 107.2 (19) |
C12—C13—H13 | 117.4 (12) | C29—C28—H28 | 105.5 (14) |
C19—C114—C113 | 121.00 (14) | C29—C28—H28' | 111.8 (14) |
N12—C114—C113 | 119.68 (14) | C29—C28—H28'' | 110.9 (14) |
C15—C14—H14 | 119.1 (14) | C29—C210—C211 | 121.32 (16) |
C13—C14—H14 | 120.7 (14) | C210—C211—C212 | 120.64 (17) |
N12—C114—C19 | 119.27 (14) | C211—C212—C213 | 119.35 (17) |
C14—C15—H15 | 123.6 (13) | C212—C213—C214 | 119.80 (16) |
C16—C15—H15 | 116.7 (13) | N22—C214—C213 | 118.60 (14) |
S1—C115—N11 | 121.17 (12) | C29—C214—C213 | 121.47 (15) |
N11—C115—N12 | 117.76 (14) | N22—C214—C29 | 119.88 (14) |
S1—C115—N12 | 121.07 (12) | N21—C215—N22 | 117.05 (14) |
C15—C16—H16 | 122.0 (9) | S2—C215—N21 | 121.75 (12) |
C17—C16—H16 | 118.6 (9) | S2—C215—N22 | 121.19 (12) |
H18'—C18—H18'' | 106.1 (18) | C29—C210—H210 | 118.5 (11) |
C19—C18—H18'' | 111.2 (13) | C211—C210—H210 | 120.1 (11) |
C19—C18—H18' | 111.4 (14) | C210—C211—H211 | 119.0 (12) |
C19—C18—H18 | 111.7 (13) | C212—C211—H211 | 120.4 (12) |
H18—C18—H18' | 110.1 (19) | C211—C212—H212 | 120.9 (12) |
H18—C18—H18'' | 106.1 (18) | C213—C212—H212 | 119.7 (12) |
C19—C110—H110 | 117.8 (12) | C212—C213—H213 | 121.0 (11) |
C111—C110—H110 | 120.9 (12) | C214—C213—H213 | 119.2 (11) |
C115—N11—C17—C12 | −88.0 (2) | C18—C19—C114—C113 | −176.91 (15) |
C115—N11—C17—C16 | 93.4 (2) | C110—C19—C114—C113 | 1.8 (2) |
C17—N11—C115—S1 | −6.9 (2) | C18—C19—C114—N12 | 0.4 (2) |
C17—N11—C115—N12 | 174.27 (15) | C18—C19—C110—C111 | 177.41 (17) |
C115—N12—C114—C19 | 125.25 (17) | C114—C19—C110—C111 | −1.3 (3) |
C115—N12—C114—C113 | −57.4 (2) | C21—C22—C23—C24 | −179.82 (17) |
C114—N12—C115—S1 | 173.60 (12) | C27—C22—C23—C24 | −0.3 (2) |
C114—N12—C115—N11 | −7.5 (2) | C21—C22—C27—N21 | 0.1 (2) |
C215—N21—C27—C22 | 88.23 (19) | C21—C22—C27—C26 | −178.88 (16) |
C215—N21—C27—C26 | −92.76 (19) | C23—C22—C27—N21 | −179.46 (14) |
C27—N21—C215—S2 | 8.5 (2) | C23—C22—C27—C26 | 1.5 (2) |
C27—N21—C215—N22 | −171.98 (14) | C22—C23—C24—C25 | −0.5 (3) |
C215—N22—C214—C29 | −84.5 (2) | C23—C24—C25—C26 | 0.0 (3) |
C215—N22—C214—C213 | 98.11 (19) | C24—C25—C26—C27 | 1.2 (2) |
C214—N22—C215—S2 | −174.39 (12) | C25—C26—C27—N21 | 178.96 (15) |
C214—N22—C215—N21 | 6.1 (2) | C25—C26—C27—C22 | −2.1 (2) |
C17—C12—C13—C14 | 0.1 (3) | C28—C29—C210—C211 | 179.47 (17) |
C11—C12—C17—N11 | 0.3 (2) | C214—C29—C210—C211 | −0.7 (2) |
C11—C12—C17—C16 | 178.93 (17) | C28—C29—C214—C213 | −179.87 (16) |
C13—C12—C17—N11 | −179.33 (15) | C210—C29—C214—C213 | 0.3 (2) |
C13—C12—C17—C16 | −0.7 (2) | C28—C29—C214—N22 | 2.9 (2) |
C11—C12—C13—C14 | −179.58 (18) | C210—C29—C214—N22 | −176.98 (14) |
C12—C13—C14—C15 | 0.2 (3) | C29—C210—C211—C212 | 0.6 (3) |
C13—C14—C15—C16 | 0.1 (3) | C210—C211—C212—C213 | −0.2 (3) |
C14—C15—C16—C17 | −0.7 (3) | C211—C212—C213—C214 | −0.2 (3) |
C15—C16—C17—N11 | 179.66 (16) | C212—C213—C214—N22 | 177.46 (15) |
C15—C16—C17—C12 | 1.0 (3) | C212—C213—C214—C29 | 0.2 (2) |
C110—C19—C114—N12 | 179.10 (15) |
Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x+1/2, y−1/2, −z+1/2; (iv) −x, −y+1, −z; (v) −x+1, −y+1, −z; (vi) x+1, y, z; (vii) x−1, y, z; (viii) −x+1, −y, −z; (ix) x, y−1, z; (x) −x+1, −y+2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N12—H122···S2 | 0.87 (2) | 2.49 (2) | 3.3408 (14) | 165.4 (18) |
N22—H222···S1 | 0.87 (2) | 2.43 (2) | 3.2794 (14) | 166.9 (17) |