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The two o-tolyl groups in the title compound, C15H16N2S, are trans with respect to the thio­urea unit. The asymmetric unit consists of two mol­ecules linked by N—H...S hydrogen bonds into dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806055048/sj2200sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806055048/sj2200Isup2.hkl
Contains datablock I

CCDC reference: 638527

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.046
  • wR factor = 0.105
  • Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 8.33 Ratio
Author Response: ...
  All H atoms refine well; Uiso of H16 converged to a low value.
  This is the reason for ratio of 8.33.



Alert level C PLAT245_ALERT_2_C U(iso) H16 Smaller than U(eq) C16 by ... 0.02 AngSq PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.06 PLAT420_ALERT_2_C D-H Without Acceptor N11 - H121 ... ? PLAT420_ALERT_2_C D-H Without Acceptor N21 - H221 ... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 4 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

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.

1,3-Di-o-tolylthiourea top
Crystal data top
C15H16N2SF(000) = 1088
Mr = 256.37The 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/nDx = 1.241 Mg m3
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 12.3960 (9) ÅCell parameters from 6808 reflections
b = 9.5652 (7) Åθ = 2.3–29.1°
c = 23.163 (2) ŵ = 0.22 mm1
β = 92.266 (1)°T = 100 K
V = 2744.3 (4) Å3Block, colourless
Z = 80.49 × 0.23 × 0.16 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
6776 independent reflections
Radiation source: fine focus sealed Siemens Mo tube5577 reflections with I > 2σ(I)
Parallel mounted graphite monochromatorRint = 0.034
Detector resolution: 4096x4096/62x62 (binned 512) pixels mm-1θmax = 28.3°, θmin = 2.7°
φ and ω scansh = 1616
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
k = 1212
Tmin = 0.886, Tmax = 0.966l = 3029
22738 measured reflections
Refinement top
Refinement on F2Primary atom site location: heavy-atom method
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: difference Fourier map
wR(F2) = 0.105All 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 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.20 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.47963 (3)0.74484 (4)0.15212 (2)0.0185 (1)
N110.64627 (11)0.58167 (15)0.12974 (6)0.0195 (4)
N120.47770 (11)0.48848 (14)0.10861 (6)0.0172 (4)
C110.71217 (17)0.7660 (2)0.04043 (9)0.0329 (6)
C120.75265 (13)0.78441 (18)0.10166 (8)0.0251 (5)
C130.82468 (15)0.8907 (2)0.11825 (10)0.0332 (6)
C140.86198 (15)0.9059 (2)0.17500 (11)0.0376 (7)
C150.82852 (15)0.8145 (2)0.21703 (10)0.0354 (7)
C160.75686 (14)0.7065 (2)0.20185 (9)0.0269 (5)
C170.71958 (12)0.69366 (17)0.14507 (8)0.0206 (5)
C180.41792 (16)0.2230 (2)0.15657 (8)0.0261 (6)
C190.48845 (13)0.23336 (17)0.10525 (7)0.0191 (5)
C1100.52634 (14)0.11385 (18)0.07810 (8)0.0248 (5)
C1110.58774 (14)0.12300 (19)0.02944 (8)0.0262 (5)
C1120.61274 (13)0.25207 (19)0.00640 (8)0.0218 (5)
C1130.57748 (13)0.37261 (17)0.03319 (7)0.0182 (4)
C1140.51644 (12)0.36341 (16)0.08239 (7)0.0156 (4)
C1150.53793 (12)0.59647 (16)0.12843 (7)0.0157 (4)
H110.7434 (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)*
H130.8476 (17)0.956 (2)0.0878 (9)0.035 (6)*
H140.9114 (18)0.978 (2)0.1856 (10)0.042 (6)*
H150.8510 (18)0.820 (2)0.2553 (10)0.036 (6)*
H160.7343 (13)0.6321 (17)0.2313 (7)0.006 (4)*
H180.4460 (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)*
H1100.5075 (16)0.025 (2)0.0937 (9)0.029 (5)*
H1110.6107 (17)0.039 (2)0.0118 (9)0.035 (6)*
H1120.6531 (16)0.261 (2)0.0273 (9)0.025 (5)*
H1130.5935 (15)0.463 (2)0.0182 (8)0.018 (5)*
H1210.6717 (16)0.506 (2)0.1170 (8)0.026 (5)*
H1220.4078 (18)0.497 (2)0.1109 (9)0.030 (5)*
S20.20838 (3)0.48035 (4)0.09584 (2)0.0194 (1)
N210.04656 (11)0.64940 (15)0.12219 (6)0.0189 (4)
N220.21681 (11)0.74524 (14)0.12945 (6)0.0173 (4)
C210.00271 (17)0.4945 (2)0.22449 (8)0.0285 (6)
C220.04967 (13)0.45726 (17)0.16709 (7)0.0187 (5)
C230.12127 (14)0.34519 (18)0.16081 (8)0.0223 (5)
C240.16923 (13)0.31106 (18)0.10754 (8)0.0232 (5)
C250.14683 (13)0.39005 (19)0.05912 (8)0.0226 (5)
C260.07660 (13)0.50254 (18)0.06428 (7)0.0191 (4)
C270.02766 (12)0.53382 (16)0.11744 (7)0.0168 (4)
C280.12245 (17)0.9518 (2)0.05150 (8)0.0294 (6)
C290.13615 (13)0.97793 (17)0.11524 (7)0.0201 (5)
C2100.10626 (14)1.10519 (18)0.13975 (8)0.0246 (5)
C2110.11820 (14)1.12838 (19)0.19848 (9)0.0268 (5)
C2120.16143 (15)1.0259 (2)0.23491 (8)0.0271 (5)
C2130.19259 (14)0.89874 (18)0.21176 (8)0.0219 (5)
C2140.17978 (12)0.87550 (16)0.15252 (7)0.0173 (4)
C2150.15426 (12)0.63346 (16)0.11717 (7)0.0156 (4)
H210.0813 (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)*
H230.1361 (16)0.294 (2)0.1947 (9)0.028 (5)*
H240.2176 (16)0.233 (2)0.1047 (8)0.025 (5)*
H250.1780 (15)0.368 (2)0.0229 (8)0.022 (5)*
H260.0607 (15)0.561 (2)0.0327 (8)0.019 (5)*
H280.1000 (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)*
H2100.0801 (15)1.179 (2)0.1144 (8)0.025 (5)*
H2110.0980 (17)1.218 (2)0.2137 (9)0.031 (5)*
H2120.1672 (17)1.040 (2)0.2753 (10)0.033 (6)*
H2130.2218 (15)0.826 (2)0.2360 (8)0.020 (5)*
H2210.0255 (17)0.722 (2)0.1378 (9)0.027 (5)*
H2220.2861 (18)0.732 (2)0.1322 (9)0.028 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0141 (2)0.0142 (2)0.0274 (2)0.0011 (2)0.0030 (2)0.0055 (2)
N110.0142 (7)0.0135 (7)0.0309 (8)0.0013 (5)0.0010 (5)0.0063 (6)
N120.0125 (7)0.0141 (6)0.0251 (7)0.0008 (5)0.0030 (5)0.0033 (5)
C110.0311 (11)0.0268 (10)0.0412 (12)0.0026 (8)0.0054 (9)0.0078 (9)
C120.0151 (8)0.0172 (8)0.0433 (11)0.0030 (6)0.0056 (7)0.0027 (7)
C130.0192 (9)0.0231 (9)0.0579 (14)0.0026 (8)0.0104 (9)0.0044 (9)
C140.0170 (9)0.0274 (10)0.0690 (15)0.0060 (8)0.0076 (9)0.0195 (10)
C150.0212 (9)0.0395 (12)0.0453 (13)0.0009 (8)0.0019 (8)0.0207 (10)
C160.0167 (8)0.0266 (9)0.0375 (10)0.0014 (7)0.0027 (7)0.0098 (8)
C170.0098 (7)0.0160 (8)0.0362 (10)0.0009 (6)0.0037 (6)0.0083 (7)
C180.0280 (10)0.0235 (9)0.0267 (10)0.0027 (8)0.0012 (7)0.0081 (7)
C190.0170 (8)0.0172 (8)0.0227 (8)0.0014 (6)0.0042 (6)0.0012 (6)
C1100.0239 (9)0.0130 (8)0.0370 (10)0.0007 (7)0.0046 (7)0.0002 (7)
C1110.0214 (9)0.0189 (9)0.0379 (10)0.0028 (7)0.0045 (7)0.0127 (7)
C1120.0150 (8)0.0264 (9)0.0237 (9)0.0021 (7)0.0021 (6)0.0076 (7)
C1130.0141 (7)0.0174 (8)0.0229 (8)0.0008 (6)0.0023 (6)0.0009 (6)
C1140.0124 (7)0.0136 (7)0.0205 (8)0.0016 (6)0.0033 (6)0.0029 (6)
C1150.0162 (7)0.0139 (7)0.0172 (8)0.0005 (6)0.0021 (6)0.0006 (6)
S20.0139 (2)0.0152 (2)0.0290 (2)0.0023 (2)0.0009 (2)0.0055 (2)
N210.0141 (7)0.0131 (7)0.0295 (8)0.0010 (5)0.0028 (5)0.0041 (6)
N220.0110 (6)0.0142 (6)0.0266 (7)0.0020 (5)0.0015 (5)0.0019 (5)
C210.0359 (11)0.0261 (10)0.0229 (9)0.0043 (8)0.0061 (8)0.0016 (7)
C220.0167 (8)0.0173 (8)0.0220 (8)0.0050 (6)0.0001 (6)0.0005 (6)
C230.0197 (8)0.0191 (8)0.0285 (9)0.0036 (7)0.0057 (7)0.0051 (7)
C240.0134 (8)0.0177 (8)0.0386 (10)0.0002 (7)0.0014 (7)0.0034 (7)
C250.0155 (8)0.0273 (9)0.0249 (9)0.0022 (7)0.0014 (7)0.0072 (7)
C260.0142 (7)0.0225 (8)0.0208 (8)0.0030 (6)0.0039 (6)0.0013 (7)
C270.0118 (7)0.0152 (7)0.0235 (8)0.0017 (6)0.0016 (6)0.0014 (6)
C280.0319 (10)0.0313 (10)0.0251 (10)0.0074 (9)0.0024 (8)0.0062 (8)
C290.0140 (7)0.0195 (8)0.0271 (9)0.0002 (6)0.0033 (6)0.0019 (7)
C2100.0179 (8)0.0157 (8)0.0403 (11)0.0008 (7)0.0027 (7)0.0037 (7)
C2110.0187 (8)0.0178 (8)0.0440 (11)0.0001 (7)0.0009 (7)0.0084 (8)
C2120.0253 (9)0.0274 (9)0.0284 (10)0.0004 (8)0.0002 (7)0.0093 (8)
C2130.0193 (8)0.0199 (8)0.0264 (9)0.0009 (7)0.0009 (7)0.0011 (7)
C2140.0115 (7)0.0139 (7)0.0267 (9)0.0008 (6)0.0038 (6)0.0009 (6)
C2150.0156 (7)0.0151 (7)0.0162 (8)0.0019 (6)0.0007 (6)0.0018 (6)
Geometric parameters (Å, º) top
S1—C1151.6938 (16)C18—H180.95 (2)
S2—C2151.6927 (16)C18—H18'0.97 (3)
N11—C1151.350 (2)C18—H18''1.00 (2)
N11—C171.440 (2)C110—H1100.96 (2)
N12—C1141.433 (2)C111—H1110.95 (2)
N12—C1151.345 (2)C112—H1120.95 (2)
N11—H1210.847 (19)C113—H1130.956 (19)
N12—H1220.87 (2)C21—C221.499 (2)
N21—C271.440 (2)C22—C271.399 (2)
N21—C2151.353 (2)C22—C231.396 (2)
N22—C2151.345 (2)C23—C241.387 (3)
N22—C2141.438 (2)C24—C251.389 (3)
N21—H2210.83 (2)C25—C261.386 (2)
N22—H2220.87 (2)C26—C271.384 (2)
C11—C121.496 (3)C28—C291.500 (2)
C12—C171.402 (2)C29—C2101.399 (2)
C12—C131.397 (3)C29—C2141.400 (2)
C13—C141.384 (3)C21—H210.98 (2)
C14—C151.384 (3)C21—H21'0.99 (2)
C15—C161.398 (3)C21—H21''0.94 (3)
C16—C171.382 (3)C23—H230.95 (2)
C18—C191.507 (3)C24—H240.958 (19)
C19—C1101.395 (2)C25—H250.934 (19)
C19—C1141.401 (2)C26—H260.948 (19)
C110—C1111.388 (3)C28—H28'0.98 (2)
C11—H11'1.01 (3)C28—H28''0.99 (3)
C11—H11''1.01 (2)C28—H280.98 (3)
C111—C1121.385 (3)C210—C2111.381 (3)
C11—H111.02 (3)C211—C2121.387 (3)
C112—C1131.388 (2)C212—C2131.390 (3)
C113—C1141.395 (2)C213—C2141.393 (2)
C13—H130.99 (2)C210—H2100.966 (19)
C14—H140.95 (2)C211—H2110.96 (2)
C15—H150.92 (2)C212—H2120.95 (2)
C16—H161.032 (16)C213—H2130.956 (19)
S1···N223.2794 (14)C215···C283.420 (2)
S1···C123.6436 (17)C210···H14vii2.94 (2)
S1···C163.5997 (18)C211···H213ii3.094 (19)
S2···C263.5853 (17)C211···H14vii2.94 (2)
S2···N123.3408 (14)C214···H2212.42 (2)
S2···C223.6636 (17)C215···H212.99 (2)
S1···H110i3.03 (2)C215···H28''3.02 (3)
S1···H2222.43 (2)H11···H132.36 (3)
S1···H21''ii2.88 (3)H11···H111i2.51 (3)
S1···H212iii3.20 (2)H11···H28x2.55 (3)
S2···H18''2.91 (2)H11···C28x3.04 (3)
S2···H1222.49 (2)H11'···N112.79 (2)
S2···H25iv3.119 (19)H11'···C26vi2.97 (3)
N11···C1133.095 (2)H11''···N112.81 (2)
N12···S23.3408 (14)H11''···C1152.96 (2)
N21···C293.339 (2)H13···H112.36 (3)
N22···S13.2794 (14)H14···C210vi2.94 (2)
N11···H1132.874 (19)H14···C211vi2.94 (2)
N11···H11'2.79 (2)H18···N122.78 (2)
N11···H11''2.81 (2)H18'···H1102.37 (3)
N12···H18''2.90 (2)H18'···C21iii2.97 (2)
N12···H182.78 (2)H18''···S22.91 (2)
N21···H21'2.80 (2)H18''···N122.90 (2)
N21···H28''2.84 (3)H18''···H1222.55 (3)
N21···H212.83 (2)H21···N212.83 (2)
N22···H28'2.81 (2)H21···C2152.99 (2)
N22···H28''2.90 (2)H21···H211ix2.55 (3)
N22···H112v2.92 (2)H21'···C16vii3.09 (2)
C11···C1153.435 (3)H21'···C18ii3.03 (2)
C12···S13.6436 (17)H21'···N212.80 (2)
C12···C26vi3.556 (2)H21'···C15vii2.89 (2)
C16···C22vi3.498 (2)H21''···H232.36 (3)
C16···S13.5997 (18)H21''···S1iii2.88 (3)
C17···C27vi3.567 (2)H23···H21''2.36 (3)
C21···C2153.442 (3)H23···C16iii2.99 (2)
C22···C16vii3.498 (2)H24···C112vii3.043 (19)
C22···S23.6636 (17)H25···H112vii2.57 (3)
C24···C112vii3.551 (2)H25···C113vii3.050 (19)
C24···C113vii3.570 (2)H25···C112vii2.833 (19)
C25···C112vii3.439 (2)H25···S2iv3.119 (19)
C25···C113vii3.450 (2)H26···C26iv2.935 (19)
C26···C12vii3.556 (2)H26···H26iv2.47 (3)
C26···C26iv3.595 (2)H28···H2102.29 (3)
C26···S23.5853 (17)H28···H11x2.55 (3)
C27···C17vii3.567 (2)H28'···N222.81 (2)
C28···C2153.420 (2)H28''···N212.84 (3)
C29···N213.339 (2)H28''···N222.90 (2)
C11···H111i2.96 (2)H28''···C2153.02 (3)
C111···C111viii3.449 (3)H110···S1ix3.03 (2)
C112···C25vi3.439 (2)H110···H18'2.37 (3)
C112···C24vi3.551 (2)H111···C11ix2.96 (2)
C113···C24vi3.570 (2)H111···C111viii3.03 (2)
C113···C113v3.429 (2)H111···H11ix2.51 (3)
C113···N113.095 (2)H111···C110viii3.01 (2)
C113···C25vi3.450 (2)H112···H25vi2.57 (3)
C13···H221vi2.99 (2)H112···H222v2.57 (3)
C14···H221vi2.84 (2)H112···N22v2.92 (2)
C115···C113.435 (3)H113···N112.874 (19)
C15···H21'vi2.89 (2)H113···H113v2.54 (3)
C16···H21'vi3.09 (2)H113···C113v2.860 (19)
C16···H23ii2.99 (2)H113···C1152.960 (19)
C18···H21'iii3.03 (2)H113···H1212.48 (3)
C18···H1222.827 (19)H121···C24vi2.73 (2)
C21···H18'ii2.97 (2)H121···C1142.47 (2)
C21···H211ix2.91 (2)H121···C25vi2.89 (2)
C21···H2212.98 (2)H121···C1132.565 (19)
C22···H211ix3.10 (2)H121···H1132.48 (3)
C24···H121vii2.73 (2)H122···H18''2.55 (3)
C25···H121vii2.89 (2)H122···S22.49 (2)
C26···H11'vii2.97 (3)H122···C182.827 (19)
C26···H26iv2.935 (19)H210···H282.29 (3)
C28···H11x3.04 (3)H211···C21i2.91 (2)
C29···H2212.86 (2)H211···C22i3.10 (2)
C110···H111viii3.01 (2)H211···H21i2.55 (3)
C111···H111viii3.03 (2)H212···S1ii3.20 (2)
C112···H24vi3.043 (19)H213···C211iii3.094 (19)
C112···H25vi2.833 (19)H221···C13vii2.99 (2)
C113···H1212.565 (19)H221···C14vii2.84 (2)
C113···H25vi3.050 (19)H221···C212.98 (2)
C113···H113v2.860 (19)H221···C292.86 (2)
C114···H1212.47 (2)H221···C2142.42 (2)
C115···H1132.960 (19)H222···S12.43 (2)
C115···H11''2.96 (2)H222···H112v2.57 (3)
C215···C213.442 (3)
C17—N11—C115123.04 (14)C112—C111—H111120.9 (13)
C114—N12—C115126.52 (13)C110—C111—H111118.6 (13)
C17—N11—H121118.8 (13)C111—C112—H112122.1 (12)
C115—N11—H121117.7 (13)C113—C112—H112118.6 (12)
C114—N12—H122117.0 (13)C114—C113—H113118.8 (11)
C115—N12—H122116.5 (13)C112—C113—H113121.0 (11)
C27—N21—C215122.45 (14)C21—C22—C23121.75 (15)
C214—N22—C215125.29 (13)C21—C22—C27120.85 (15)
C27—N21—H221117.7 (14)C23—C22—C27117.40 (15)
C215—N21—H221117.4 (15)C22—C23—C24121.46 (16)
C215—N22—H222117.4 (13)C23—C24—C25119.85 (16)
C214—N22—H222115.4 (13)C24—C25—C26119.83 (16)
C11—C12—C17120.70 (16)C25—C26—C27119.76 (15)
C11—C12—C13122.23 (17)N21—C27—C22118.94 (14)
C13—C12—C17117.08 (17)N21—C27—C26119.37 (14)
C12—C13—C14121.58 (19)C22—C27—C26121.69 (15)
C13—C14—C15120.24 (18)C210—C29—C214117.42 (15)
C14—C15—C16119.7 (2)C28—C29—C210121.51 (15)
C15—C16—C17119.35 (18)C28—C29—C214121.07 (15)
C12—C17—C16122.09 (16)C22—C21—H21''111.1 (16)
N11—C17—C12118.90 (16)H21—C21—H21'111.2 (17)
N11—C17—C16118.99 (15)C22—C21—H21'109.6 (12)
C18—C19—C114121.12 (15)C22—C21—H21108.5 (12)
C110—C19—C114117.67 (15)H21'—C21—H21''108 (2)
C18—C19—C110121.20 (15)H21—C21—H21''108.6 (19)
C19—C110—C111121.32 (16)C22—C23—H23116.9 (12)
C110—C111—C112120.50 (17)C24—C23—H23121.6 (12)
C12—C11—H11''109.0 (13)C25—C24—H24120.9 (11)
H11—C11—H11''108.5 (18)C23—C24—H24119.3 (11)
H11—C11—H11'110 (2)C24—C25—H25120.9 (12)
C12—C11—H11110.5 (14)C26—C25—H25119.3 (12)
H11'—C11—H11''108.4 (18)C25—C26—H26122.7 (11)
C12—C11—H11'110.1 (14)C27—C26—H26117.5 (11)
C111—C112—C113119.27 (16)H28—C28—H28'106.6 (18)
C112—C113—C114120.21 (15)H28—C28—H28''115 (2)
C14—C13—H13121.0 (12)H28'—C28—H28''107.2 (19)
C12—C13—H13117.4 (12)C29—C28—H28105.5 (14)
C19—C114—C113121.00 (14)C29—C28—H28'111.8 (14)
N12—C114—C113119.68 (14)C29—C28—H28''110.9 (14)
C15—C14—H14119.1 (14)C29—C210—C211121.32 (16)
C13—C14—H14120.7 (14)C210—C211—C212120.64 (17)
N12—C114—C19119.27 (14)C211—C212—C213119.35 (17)
C14—C15—H15123.6 (13)C212—C213—C214119.80 (16)
C16—C15—H15116.7 (13)N22—C214—C213118.60 (14)
S1—C115—N11121.17 (12)C29—C214—C213121.47 (15)
N11—C115—N12117.76 (14)N22—C214—C29119.88 (14)
S1—C115—N12121.07 (12)N21—C215—N22117.05 (14)
C15—C16—H16122.0 (9)S2—C215—N21121.75 (12)
C17—C16—H16118.6 (9)S2—C215—N22121.19 (12)
H18'—C18—H18''106.1 (18)C29—C210—H210118.5 (11)
C19—C18—H18''111.2 (13)C211—C210—H210120.1 (11)
C19—C18—H18'111.4 (14)C210—C211—H211119.0 (12)
C19—C18—H18111.7 (13)C212—C211—H211120.4 (12)
H18—C18—H18'110.1 (19)C211—C212—H212120.9 (12)
H18—C18—H18''106.1 (18)C213—C212—H212119.7 (12)
C19—C110—H110117.8 (12)C212—C213—H213121.0 (11)
C111—C110—H110120.9 (12)C214—C213—H213119.2 (11)
C115—N11—C17—C1288.0 (2)C18—C19—C114—C113176.91 (15)
C115—N11—C17—C1693.4 (2)C110—C19—C114—C1131.8 (2)
C17—N11—C115—S16.9 (2)C18—C19—C114—N120.4 (2)
C17—N11—C115—N12174.27 (15)C18—C19—C110—C111177.41 (17)
C115—N12—C114—C19125.25 (17)C114—C19—C110—C1111.3 (3)
C115—N12—C114—C11357.4 (2)C21—C22—C23—C24179.82 (17)
C114—N12—C115—S1173.60 (12)C27—C22—C23—C240.3 (2)
C114—N12—C115—N117.5 (2)C21—C22—C27—N210.1 (2)
C215—N21—C27—C2288.23 (19)C21—C22—C27—C26178.88 (16)
C215—N21—C27—C2692.76 (19)C23—C22—C27—N21179.46 (14)
C27—N21—C215—S28.5 (2)C23—C22—C27—C261.5 (2)
C27—N21—C215—N22171.98 (14)C22—C23—C24—C250.5 (3)
C215—N22—C214—C2984.5 (2)C23—C24—C25—C260.0 (3)
C215—N22—C214—C21398.11 (19)C24—C25—C26—C271.2 (2)
C214—N22—C215—S2174.39 (12)C25—C26—C27—N21178.96 (15)
C214—N22—C215—N216.1 (2)C25—C26—C27—C222.1 (2)
C17—C12—C13—C140.1 (3)C28—C29—C210—C211179.47 (17)
C11—C12—C17—N110.3 (2)C214—C29—C210—C2110.7 (2)
C11—C12—C17—C16178.93 (17)C28—C29—C214—C213179.87 (16)
C13—C12—C17—N11179.33 (15)C210—C29—C214—C2130.3 (2)
C13—C12—C17—C160.7 (2)C28—C29—C214—N222.9 (2)
C11—C12—C13—C14179.58 (18)C210—C29—C214—N22176.98 (14)
C12—C13—C14—C150.2 (3)C29—C210—C211—C2120.6 (3)
C13—C14—C15—C160.1 (3)C210—C211—C212—C2130.2 (3)
C14—C15—C16—C170.7 (3)C211—C212—C213—C2140.2 (3)
C15—C16—C17—N11179.66 (16)C212—C213—C214—N22177.46 (15)
C15—C16—C17—C121.0 (3)C212—C213—C214—C290.2 (2)
C110—C19—C114—N12179.10 (15)
Symmetry codes: (i) x, y+1, z; (ii) x+1/2, y+1/2, z+1/2; (iii) x+1/2, y1/2, z+1/2; (iv) x, y+1, z; (v) x+1, y+1, z; (vi) x+1, y, z; (vii) x1, y, z; (viii) x+1, y, z; (ix) x, y1, z; (x) x+1, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N12—H122···S20.87 (2)2.49 (2)3.3408 (14)165.4 (18)
N22—H222···S10.87 (2)2.43 (2)3.2794 (14)166.9 (17)
 

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