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The title compound, C18H26N2O4S, with two virtually identical mol­ecules in the asymmetric unit, is found to adopt a distorted S conformation, with the carbonyl of the benzoyl group facing the opposite direction to the N-H amine bond, which lies in roughly the same direction as the C=S bond of the thio­urea. The C-N bond of the thio­urea on the acyl side of the mol­ecule is much longer than the corresponding bond on the opposite side.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043054/tk2087sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043054/tk2087Isup2.hkl
Contains datablock I

CCDC reference: 628417

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.048
  • wR factor = 0.115
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.93 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.89 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.57 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for S1A - C2A .. 5.73 su PLAT230_ALERT_2_C Hirshfeld Test Diff for S1B - C2B .. 5.42 su PLAT432_ALERT_2_C Short Inter X...Y Contact O1B .. C9B .. 2.99 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C18 H26 N2 O4 S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 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 5 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, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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: X-SEED (Barbour, 2001).

N,N-(Heptane-2,6-diyl)-N'-(3,4,5-methoxybenzoyl)thiourea top
Crystal data top
C18H26N2O4SZ = 4
Mr = 366.47F(000) = 784
Triclinic, P1Dx = 1.279 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.427 (2) ÅCell parameters from 18232 reflections
b = 12.666 (2) Åθ = 1.9–25.0°
c = 13.894 (2) ŵ = 0.19 mm1
α = 96.486 (2)°T = 173 K
β = 91.758 (3)°Block, colourless
γ = 118.402 (2)°0.2 × 0.2 × 0.15 mm
V = 1902.5 (5) Å3
Data collection top
Bruker APEX CCD area-detector
diffractometer
5552 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
Graphite monochromatorθmax = 25.0°, θmin = 1.9°
ω scansh = 1414
18232 measured reflectionsk = 1515
6672 independent reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0491P)2 + 1.552P]
where P = (Fo2 + 2Fc2)/3
6672 reflections(Δ/σ)max < 0.001
461 parametersΔρmax = 0.79 e Å3
0 restraintsΔρmin = 0.27 e Å3
Special details top

Experimental. Selected assigned vibrational frequencies (IR, KBr pellets, cm-1) are 3167 (N–H str), 1674 (C=O str), 1586, (N–H oop), 1421 (C2–N2 str), 1125 (N1–C2 str), 1216 (C1–N1 str) and 770 (C=S str).

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1A0.33229 (5)0.50582 (5)0.06041 (4)0.02321 (15)
O1A0.13216 (13)0.18752 (13)0.16127 (10)0.0202 (3)
N1A0.11363 (16)0.32526 (16)0.08053 (13)0.0181 (4)
H1A0.095 (2)0.380 (2)0.0871 (17)0.022*
C1A0.07963 (19)0.24548 (18)0.14817 (15)0.0169 (4)
S1B0.91223 (5)0.39797 (5)0.10656 (4)0.02402 (15)
O1B0.87791 (15)0.40905 (14)0.37952 (11)0.0269 (4)
N1B0.77448 (17)0.41027 (16)0.24952 (13)0.0193 (4)
H1B0.749 (2)0.449 (2)0.2110 (18)0.023*
C1B0.8189 (2)0.44933 (19)0.33513 (15)0.0190 (5)
O2A0.18138 (15)0.08622 (15)0.40937 (11)0.0278 (4)
N2A0.23427 (15)0.27498 (16)0.02222 (12)0.0178 (4)
C2A0.22399 (19)0.35953 (19)0.03595 (15)0.0171 (4)
O2B0.83657 (17)0.68989 (16)0.59109 (12)0.0348 (4)
N2B0.74695 (16)0.21672 (16)0.23992 (12)0.0183 (4)
C2B0.8073 (2)0.3338 (2)0.20349 (15)0.0194 (5)
O3A0.33308 (14)0.16367 (14)0.34987 (11)0.0253 (4)
C3A0.02784 (19)0.23227 (18)0.20147 (15)0.0177 (5)
O3B0.68254 (16)0.75442 (15)0.50842 (12)0.0300 (4)
C3B0.78538 (19)0.53597 (18)0.37404 (15)0.0188 (5)
O4A0.29145 (15)0.28974 (16)0.20069 (12)0.0299 (4)
C4A0.0496 (2)0.16896 (19)0.28080 (15)0.0196 (5)
H2A0.00470.14030.30020.024*
O4B0.59480 (15)0.68560 (14)0.34155 (11)0.0272 (4)
C4B0.8326 (2)0.57515 (19)0.46023 (16)0.0213 (5)
H12B0.88830.55200.48820.026*
C5A0.1506 (2)0.14808 (19)0.33106 (15)0.0206 (5)
C5B0.7983 (2)0.6480 (2)0.50539 (16)0.0230 (5)
C6A0.22996 (19)0.19032 (19)0.30268 (16)0.0202 (5)
C6B0.7176 (2)0.68294 (19)0.46292 (16)0.0214 (5)
C7A0.2072 (2)0.2537 (2)0.22316 (16)0.0206 (5)
C7B0.67293 (19)0.64604 (19)0.37530 (16)0.0197 (5)
C8A0.1065 (2)0.27454 (19)0.17212 (16)0.0200 (5)
H12A0.09150.31720.11770.024*
C8B0.70570 (19)0.57154 (19)0.33057 (16)0.0193 (5)
H2B0.67440.54510.27120.023*
C9A0.1048 (2)0.0383 (2)0.43941 (18)0.0330 (6)
H4A0.10170.01620.38490.049*
H5A0.13840.00680.49370.049*
H3A0.02170.10500.46020.049*
C9B0.9235 (3)0.6594 (3)0.6334 (2)0.0545 (9)
H11B0.88600.57110.64990.082*
H9B0.94810.69720.69240.082*
H10B0.99600.68910.58670.082*
C10A0.3246 (2)0.2640 (2)0.41513 (17)0.0297 (6)
H7A0.25470.29290.46420.045*
H6A0.40050.23800.44730.045*
H8A0.31300.32980.37840.045*
C10B0.5677 (3)0.6832 (3)0.56688 (19)0.0408 (7)
H6B0.50440.63520.52610.061*
H7B0.54410.73690.59620.061*
H8B0.57600.62860.61840.061*
C11A0.2668 (2)0.3641 (2)0.12534 (18)0.0331 (6)
H11A0.18660.43690.14180.050*
H9A0.33090.38780.11890.050*
H10A0.26620.31850.06370.050*
C11B0.5577 (2)0.6651 (2)0.24630 (17)0.0285 (5)
H4B0.63070.69940.19940.043*
H5B0.50780.70420.22920.043*
H3B0.50920.57770.24490.043*
C12A0.35399 (19)0.30603 (19)0.06167 (15)0.0184 (5)
H13A0.41760.38150.02020.022*
C12B0.7701 (2)0.1300 (2)0.19053 (17)0.0254 (5)
H13B0.85550.17640.15740.030*
C13A0.3885 (2)0.2071 (2)0.05115 (17)0.0230 (5)
H18A0.40560.20630.01880.028*
H17A0.46440.22540.08300.028*
C13B0.7661 (2)0.0291 (2)0.26421 (18)0.0278 (5)
H17B0.76960.03310.22900.033*
H18B0.83940.06320.30080.033*
C14A0.2855 (2)0.0815 (2)0.09684 (18)0.0315 (6)
H20A0.30930.01870.08750.038*
H19A0.27070.07970.16760.038*
C14B0.6516 (2)0.0308 (2)0.33548 (19)0.0307 (6)
H20B0.65370.09420.38280.037*
H19B0.57750.06950.30030.037*
C15A0.1677 (2)0.0558 (2)0.04665 (18)0.0314 (6)
H22A0.10000.02450.07600.038*
H21A0.18230.05290.02320.038*
C15B0.6474 (2)0.0662 (2)0.38841 (17)0.0274 (5)
H21B0.57330.02800.43570.033*
H22B0.72030.10150.42540.033*
C16A0.1292 (2)0.1523 (2)0.05638 (16)0.0250 (5)
H23A0.06400.13900.01140.030*
C16B0.6450 (2)0.1672 (2)0.31986 (15)0.0206 (5)
H23B0.66080.23450.35840.025*
C17A0.0736 (2)0.1423 (3)0.15749 (19)0.0381 (6)
H26A0.05180.20690.15960.057*
H24A0.00030.06320.17400.057*
H25A0.13340.15020.20440.057*
C17B0.5213 (2)0.1301 (2)0.27961 (18)0.0293 (5)
H24B0.52540.19920.23680.044*
H25B0.45750.10450.33350.044*
H26B0.50150.06270.24260.044*
C18A0.3553 (2)0.3353 (2)0.16559 (17)0.0285 (5)
H14A0.30420.26030.21040.043*
H15A0.43990.37250.18360.043*
H16A0.32270.39170.16930.043*
C18B0.6835 (3)0.0831 (3)0.11152 (19)0.0414 (7)
H16B0.60230.02040.14160.062*
H15B0.71630.04860.06670.062*
H14B0.67620.15020.07550.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0220 (3)0.0164 (3)0.0282 (3)0.0065 (2)0.0104 (2)0.0024 (2)
O1A0.0217 (8)0.0223 (8)0.0195 (8)0.0125 (7)0.0048 (6)0.0041 (6)
N1A0.0190 (9)0.0182 (10)0.0213 (10)0.0114 (8)0.0066 (8)0.0052 (8)
C1A0.0171 (11)0.0137 (10)0.0151 (11)0.0046 (9)0.0002 (9)0.0028 (8)
S1B0.0278 (3)0.0249 (3)0.0192 (3)0.0139 (3)0.0051 (2)0.0012 (2)
O1B0.0361 (9)0.0337 (9)0.0244 (9)0.0263 (8)0.0099 (7)0.0086 (7)
N1B0.0268 (10)0.0198 (10)0.0168 (9)0.0161 (9)0.0027 (8)0.0008 (8)
C1B0.0212 (11)0.0181 (11)0.0180 (11)0.0101 (10)0.0007 (9)0.0009 (9)
O2A0.0334 (9)0.0337 (9)0.0234 (9)0.0191 (8)0.0140 (7)0.0144 (7)
N2A0.0152 (9)0.0184 (9)0.0177 (9)0.0063 (8)0.0045 (7)0.0022 (7)
C2A0.0177 (11)0.0229 (11)0.0138 (10)0.0114 (9)0.0035 (8)0.0064 (9)
O2B0.0491 (11)0.0468 (11)0.0328 (10)0.0374 (10)0.0263 (9)0.0247 (8)
N2B0.0246 (10)0.0195 (10)0.0146 (9)0.0137 (8)0.0006 (8)0.0021 (7)
C2B0.0246 (12)0.0242 (12)0.0153 (11)0.0160 (10)0.0057 (9)0.0042 (9)
O3A0.0227 (8)0.0272 (9)0.0249 (9)0.0108 (7)0.0132 (7)0.0030 (7)
C3A0.0193 (11)0.0147 (10)0.0153 (11)0.0061 (9)0.0022 (9)0.0021 (8)
O3B0.0414 (10)0.0321 (9)0.0317 (9)0.0266 (8)0.0140 (8)0.0166 (8)
C3B0.0209 (11)0.0148 (11)0.0193 (11)0.0083 (9)0.0011 (9)0.0006 (9)
O4A0.0284 (9)0.0450 (10)0.0284 (9)0.0248 (8)0.0135 (7)0.0155 (8)
C4A0.0204 (11)0.0199 (11)0.0174 (11)0.0095 (9)0.0016 (9)0.0007 (9)
O4B0.0376 (10)0.0332 (9)0.0263 (9)0.0270 (8)0.0142 (7)0.0134 (7)
C4B0.0231 (12)0.0206 (11)0.0244 (12)0.0135 (10)0.0058 (9)0.0041 (9)
C5A0.0245 (12)0.0171 (11)0.0159 (11)0.0066 (10)0.0055 (9)0.0019 (9)
C5B0.0267 (12)0.0212 (12)0.0237 (12)0.0122 (10)0.0081 (10)0.0091 (9)
C6A0.0182 (11)0.0185 (11)0.0200 (11)0.0063 (9)0.0064 (9)0.0009 (9)
C6B0.0240 (12)0.0169 (11)0.0255 (12)0.0105 (10)0.0046 (10)0.0072 (9)
C7A0.0212 (11)0.0220 (12)0.0198 (11)0.0115 (10)0.0041 (9)0.0016 (9)
C7B0.0199 (11)0.0170 (11)0.0238 (12)0.0102 (9)0.0031 (9)0.0028 (9)
C8A0.0230 (12)0.0196 (11)0.0172 (11)0.0096 (10)0.0061 (9)0.0041 (9)
C8B0.0216 (11)0.0175 (11)0.0185 (11)0.0093 (9)0.0028 (9)0.0027 (9)
C9A0.0434 (15)0.0387 (15)0.0277 (13)0.0251 (13)0.0146 (12)0.0179 (11)
C9B0.077 (2)0.074 (2)0.0564 (19)0.062 (2)0.0494 (18)0.0444 (17)
C10A0.0356 (14)0.0380 (14)0.0201 (12)0.0215 (12)0.0108 (10)0.0016 (10)
C10B0.0507 (17)0.0620 (19)0.0303 (14)0.0421 (16)0.0042 (13)0.0140 (13)
C11A0.0380 (15)0.0503 (16)0.0275 (13)0.0311 (13)0.0149 (11)0.0185 (12)
C11B0.0363 (14)0.0349 (14)0.0274 (13)0.0254 (12)0.0158 (11)0.0122 (11)
C12A0.0153 (11)0.0191 (11)0.0186 (11)0.0066 (9)0.0050 (9)0.0015 (9)
C12B0.0333 (13)0.0239 (12)0.0243 (12)0.0184 (11)0.0042 (10)0.0042 (10)
C13A0.0219 (12)0.0284 (12)0.0231 (12)0.0146 (10)0.0083 (9)0.0076 (10)
C13B0.0321 (13)0.0212 (12)0.0351 (14)0.0172 (11)0.0012 (11)0.0035 (10)
C14A0.0362 (14)0.0303 (13)0.0293 (13)0.0168 (12)0.0079 (11)0.0053 (11)
C14B0.0331 (14)0.0230 (12)0.0371 (14)0.0165 (11)0.0012 (11)0.0049 (11)
C15A0.0419 (15)0.0197 (12)0.0232 (12)0.0073 (11)0.0069 (11)0.0019 (10)
C15B0.0318 (13)0.0269 (13)0.0222 (12)0.0153 (11)0.0037 (10)0.0052 (10)
C16A0.0163 (11)0.0263 (13)0.0222 (12)0.0030 (10)0.0059 (9)0.0021 (10)
C16B0.0260 (12)0.0210 (11)0.0181 (11)0.0140 (10)0.0009 (9)0.0033 (9)
C17A0.0334 (15)0.0435 (16)0.0366 (15)0.0211 (13)0.0086 (12)0.0062 (12)
C17B0.0284 (13)0.0292 (13)0.0345 (14)0.0171 (11)0.0031 (11)0.0044 (11)
C18A0.0285 (13)0.0351 (14)0.0247 (13)0.0155 (11)0.0120 (10)0.0115 (11)
C18B0.066 (2)0.0428 (16)0.0294 (14)0.0346 (15)0.0104 (13)0.0180 (12)
Geometric parameters (Å, º) top
S1A—C2A1.678 (2)C10A—H7A0.9800
O1A—C1A1.215 (3)C10A—H6A0.9800
N1A—C1A1.384 (3)C10A—H8A0.9800
N1A—C2A1.414 (3)C10B—H6B0.9800
N2A—C2A1.326 (3)C10B—H7B0.9800
N1A—H1A0.83 (2)C10B—H8B0.9800
C1A—C3A1.495 (3)C11A—H11A0.9800
S1B—C2B1.677 (2)C11A—H9A0.9800
O1B—C1B1.221 (3)C11A—H10A0.9800
N1B—C1B1.370 (3)C11B—H4B0.9800
N1B—C2B1.419 (3)C11B—H5B0.9800
N1B—H1B0.85 (2)C11B—H3B0.9800
C1B—C3B1.492 (3)C12A—C13A1.524 (3)
O2A—C5A1.370 (3)C12A—C18A1.529 (3)
O2A—C9A1.424 (3)C12A—H13A1.0000
N2A—C16A1.487 (3)C12B—C18B1.526 (4)
N2A—C12A1.487 (3)C12B—C13B1.525 (3)
O2B—C5B1.365 (3)C12B—H13B1.0000
O2B—C9B1.430 (3)C13A—C14A1.535 (3)
N2B—C2B1.329 (3)C13A—H18A0.9900
N2B—C12B1.489 (3)C13A—H17A0.9900
N2B—C16B1.494 (3)C13B—C14B1.516 (3)
O3A—C6A1.370 (3)C13B—H17B0.9900
O3A—C10A1.434 (3)C13B—H18B0.9900
C3A—C8A1.390 (3)C14A—C15A1.548 (3)
C3A—C4A1.394 (3)C14A—H20A0.9900
O3B—C6B1.378 (3)C14A—H19A0.9900
O3B—C10B1.431 (3)C14B—C15B1.522 (3)
C3B—C4B1.387 (3)C14B—H20B0.9900
C3B—C8B1.396 (3)C14B—H19B0.9900
O4A—C7A1.367 (3)C15A—C16A1.527 (3)
O4A—C11A1.430 (3)C15A—H22A0.9900
C4A—C5A1.384 (3)C15A—H21A0.9900
C4A—H2A0.9500C15B—C16B1.519 (3)
O4B—C7B1.360 (3)C15B—H21B0.9900
O4B—C11B1.426 (3)C15B—H22B0.9900
C4B—C5B1.384 (3)C16A—C17A1.511 (3)
C4B—H12B0.9500C16A—H23A1.0000
C5A—C6A1.392 (3)C16B—C17B1.523 (3)
C5B—C6B1.396 (3)C16B—H23B1.0000
C6A—C7A1.396 (3)C17A—H26A0.9800
C6B—C7B1.390 (3)C17A—H24A0.9800
C7A—C8A1.386 (3)C17A—H25A0.9800
C7B—C8B1.387 (3)C17B—H24B0.9800
C8A—H12A0.9500C17B—H25B0.9800
C8B—H2B0.9500C17B—H26B0.9800
C9A—H4A0.9800C18A—H14A0.9800
C9A—H5A0.9800C18A—H15A0.9800
C9A—H3A0.9800C18A—H16A0.9800
C9B—H11B0.9800C18B—H16B0.9800
C9B—H9B0.9800C18B—H15B0.9800
C9B—H10B0.9800C18B—H14B0.9800
C1A—N1A—C2A121.35 (18)O4A—C11A—H10A109.5
C1A—N1A—H1A118.3 (17)H11A—C11A—H10A109.5
C2A—N1A—H1A112.4 (17)H9A—C11A—H10A109.5
O1A—C1A—N1A121.76 (19)O4B—C11B—H4B109.5
O1A—C1A—C3A122.30 (19)O4B—C11B—H5B109.5
N1A—C1A—C3A115.91 (18)H4B—C11B—H5B109.5
C1B—N1B—C2B121.57 (18)O4B—C11B—H3B109.5
C1B—N1B—H1B121.6 (16)H4B—C11B—H3B109.5
C2B—N1B—H1B113.3 (16)H5B—C11B—H3B109.5
O1B—C1B—N1B120.58 (19)N2A—C12A—C13A110.34 (17)
O1B—C1B—C3B122.04 (19)N2A—C12A—C18A111.94 (18)
N1B—C1B—C3B117.27 (18)C13A—C12A—C18A113.38 (18)
C5A—O2A—C9A117.30 (17)N2A—C12A—H13A106.9
C2A—N2A—C16A123.23 (17)C13A—C12A—H13A106.9
C2A—N2A—C12A118.96 (17)C18A—C12A—H13A106.9
C16A—N2A—C12A117.65 (16)N2B—C12B—C18B110.91 (19)
N2A—C2A—N1A118.14 (19)N2B—C12B—C13B111.11 (18)
N2A—C2A—S1A124.86 (16)C18B—C12B—C13B113.3 (2)
N1A—C2A—S1A116.99 (15)N2B—C12B—H13B107.0
C5B—O2B—C9B115.96 (18)C18B—C12B—H13B107.0
C2B—N2B—C12B118.66 (18)C13B—C12B—H13B107.0
C2B—N2B—C16B122.15 (17)C12A—C13A—C14A111.70 (19)
C12B—N2B—C16B118.65 (17)C12A—C13A—H18A109.3
N2B—C2B—N1B115.85 (19)C14A—C13A—H18A109.3
N2B—C2B—S1B126.67 (16)C12A—C13A—H17A109.3
N1B—C2B—S1B117.41 (16)C14A—C13A—H17A109.3
C6A—O3A—C10A113.93 (17)H18A—C13A—H17A107.9
C8A—C3A—C4A120.8 (2)C14B—C13B—C12B112.76 (19)
C8A—C3A—C1A122.93 (19)C14B—C13B—H17B109.0
C4A—C3A—C1A116.18 (19)C12B—C13B—H17B109.0
C6B—O3B—C10B111.62 (18)C14B—C13B—H18B109.0
C4B—C3B—C8B120.8 (2)C12B—C13B—H18B109.0
C4B—C3B—C1B116.17 (19)H17B—C13B—H18B107.8
C8B—C3B—C1B122.90 (19)C13A—C14A—C15A108.20 (19)
C7A—O4A—C11A117.29 (17)C13A—C14A—H20A110.1
C5A—C4A—C3A119.6 (2)C15A—C14A—H20A110.1
C5A—C4A—H2A120.2C13A—C14A—H19A110.1
C3A—C4A—H2A120.2C15A—C14A—H19A110.1
C7B—O4B—C11B118.07 (17)H20A—C14A—H19A108.4
C5B—C4B—C3B119.9 (2)C13B—C14B—C15B108.25 (19)
C5B—C4B—H12B120.0C13B—C14B—H20B110.0
C3B—C4B—H12B120.0C15B—C14B—H20B110.0
O2A—C5A—C4A124.5 (2)C13B—C14B—H19B110.0
O2A—C5A—C6A115.27 (19)C15B—C14B—H19B110.0
C4A—C5A—C6A120.2 (2)H20B—C14B—H19B108.4
O2B—C5B—C4B125.2 (2)C16A—C15A—C14A112.11 (19)
O2B—C5B—C6B115.27 (19)C16A—C15A—H22A109.2
C4B—C5B—C6B119.5 (2)C14A—C15A—H22A109.2
O3A—C6A—C5A119.58 (19)C16A—C15A—H21A109.2
O3A—C6A—C7A120.6 (2)C14A—C15A—H21A109.2
C5A—C6A—C7A119.72 (19)H22A—C15A—H21A107.9
O3B—C6B—C7B120.10 (19)C16B—C15B—C14B112.85 (19)
O3B—C6B—C5B119.53 (19)C16B—C15B—H21B109.0
C7B—C6B—C5B120.4 (2)C14B—C15B—H21B109.0
O4A—C7A—C8A124.5 (2)C16B—C15B—H22B109.0
O4A—C7A—C6A115.02 (19)C14B—C15B—H22B109.0
C8A—C7A—C6A120.5 (2)H21B—C15B—H22B107.8
O4B—C7B—C8B124.98 (19)N2A—C16A—C17A112.4 (2)
O4B—C7B—C6B114.79 (18)N2A—C16A—C15A109.94 (18)
C8B—C7B—C6B120.20 (19)C17A—C16A—C15A113.1 (2)
C7A—C8A—C3A119.2 (2)N2A—C16A—H23A107.0
C7A—C8A—H12A120.4C17A—C16A—H23A107.0
C3A—C8A—H12A120.4C15A—C16A—H23A107.0
C7B—C8B—C3B119.1 (2)N2B—C16B—C15B110.50 (17)
C7B—C8B—H2B120.5N2B—C16B—C17B111.37 (18)
C3B—C8B—H2B120.5C15B—C16B—C17B113.45 (19)
O2A—C9A—H4A109.5N2B—C16B—H23B107.1
O2A—C9A—H5A109.5C15B—C16B—H23B107.1
H4A—C9A—H5A109.5C17B—C16B—H23B107.1
O2A—C9A—H3A109.5C16A—C17A—H26A109.5
H4A—C9A—H3A109.5C16A—C17A—H24A109.5
H5A—C9A—H3A109.5H26A—C17A—H24A109.5
O2B—C9B—H11B109.5C16A—C17A—H25A109.5
O2B—C9B—H9B109.5H26A—C17A—H25A109.5
H11B—C9B—H9B109.5H24A—C17A—H25A109.5
O2B—C9B—H10B109.5C16B—C17B—H24B109.5
H11B—C9B—H10B109.5C16B—C17B—H25B109.5
H9B—C9B—H10B109.5H24B—C17B—H25B109.5
O3A—C10A—H7A109.5C16B—C17B—H26B109.5
O3A—C10A—H6A109.5H24B—C17B—H26B109.5
H7A—C10A—H6A109.5H25B—C17B—H26B109.5
O3A—C10A—H8A109.5C12A—C18A—H14A109.5
H7A—C10A—H8A109.5C12A—C18A—H15A109.5
H6A—C10A—H8A109.5H14A—C18A—H15A109.5
O3B—C10B—H6B109.5C12A—C18A—H16A109.5
O3B—C10B—H7B109.5H14A—C18A—H16A109.5
H6B—C10B—H7B109.5H15A—C18A—H16A109.5
O3B—C10B—H8B109.5C12B—C18B—H16B109.5
H6B—C10B—H8B109.5C12B—C18B—H15B109.5
H7B—C10B—H8B109.5H16B—C18B—H15B109.5
O4A—C11A—H11A109.5C12B—C18B—H14B109.5
O4A—C11A—H9A109.5H16B—C18B—H14B109.5
H11A—C11A—H9A109.5H15B—C18B—H14B109.5
C2A—N1A—C1A—O1A11.4 (3)C11A—O4A—C7A—C8A6.3 (3)
C2A—N1A—C1A—C3A170.47 (18)C11A—O4A—C7A—C6A174.6 (2)
C2B—N1B—C1B—O1B7.7 (3)O3A—C6A—C7A—O4A2.7 (3)
C2B—N1B—C1B—C3B176.08 (19)C5A—C6A—C7A—O4A179.21 (19)
C16A—N2A—C2A—N1A10.9 (3)O3A—C6A—C7A—C8A176.33 (19)
C12A—N2A—C2A—N1A173.76 (18)C5A—C6A—C7A—C8A0.2 (3)
C16A—N2A—C2A—S1A168.51 (16)C11B—O4B—C7B—C8B10.0 (3)
C12A—N2A—C2A—S1A6.8 (3)C11B—O4B—C7B—C6B171.9 (2)
C1A—N1A—C2A—N2A65.5 (3)O3B—C6B—C7B—O4B0.2 (3)
C1A—N1A—C2A—S1A114.96 (19)C5B—C6B—C7B—O4B179.8 (2)
C12B—N2B—C2B—N1B175.52 (18)O3B—C6B—C7B—C8B178.4 (2)
C16B—N2B—C2B—N1B4.1 (3)C5B—C6B—C7B—C8B1.7 (3)
C12B—N2B—C2B—S1B1.5 (3)O4A—C7A—C8A—C3A179.4 (2)
C16B—N2B—C2B—S1B172.97 (16)C6A—C7A—C8A—C3A0.4 (3)
C1B—N1B—C2B—N2B79.8 (3)C4A—C3A—C8A—C7A0.4 (3)
C1B—N1B—C2B—S1B102.9 (2)C1A—C3A—C8A—C7A177.09 (19)
O1A—C1A—C3A—C8A164.3 (2)O4B—C7B—C8B—C3B178.9 (2)
N1A—C1A—C3A—C8A13.8 (3)C6B—C7B—C8B—C3B1.0 (3)
O1A—C1A—C3A—C4A12.5 (3)C4B—C3B—C8B—C7B0.7 (3)
N1A—C1A—C3A—C4A169.36 (18)C1B—C3B—C8B—C7B175.65 (19)
O1B—C1B—C3B—C4B4.5 (3)C2A—N2A—C12A—C13A133.7 (2)
N1B—C1B—C3B—C4B179.35 (19)C16A—N2A—C12A—C13A50.7 (2)
O1B—C1B—C3B—C8B171.9 (2)C2A—N2A—C12A—C18A99.0 (2)
N1B—C1B—C3B—C8B4.2 (3)C16A—N2A—C12A—C18A76.6 (2)
C8A—C3A—C4A—C5A0.1 (3)C2B—N2B—C12B—C18B89.1 (2)
C1A—C3A—C4A—C5A177.02 (19)C16B—N2B—C12B—C18B82.7 (2)
C8B—C3B—C4B—C5B1.6 (3)C2B—N2B—C12B—C13B143.9 (2)
C1B—C3B—C4B—C5B175.0 (2)C16B—N2B—C12B—C13B44.3 (3)
C9A—O2A—C5A—C4A1.3 (3)N2A—C12A—C13A—C14A53.9 (2)
C9A—O2A—C5A—C6A178.3 (2)C18A—C12A—C13A—C14A72.6 (2)
C3A—C4A—C5A—O2A179.44 (19)N2B—C12B—C13B—C14B50.5 (3)
C3A—C4A—C5A—C6A0.2 (3)C18B—C12B—C13B—C14B75.1 (3)
C9B—O2B—C5B—C4B3.2 (4)C12A—C13A—C14A—C15A58.3 (2)
C9B—O2B—C5B—C6B177.3 (2)C12B—C13B—C14B—C15B58.4 (3)
C3B—C4B—C5B—O2B178.6 (2)C13A—C14A—C15A—C16A58.0 (3)
C3B—C4B—C5B—C6B0.9 (3)C13B—C14B—C15B—C16B59.3 (3)
C10A—O3A—C6A—C5A105.3 (2)C2A—N2A—C16A—C17A98.5 (2)
C10A—O3A—C6A—C7A78.2 (3)C12A—N2A—C16A—C17A76.9 (2)
O2A—C5A—C6A—O3A3.0 (3)C2A—N2A—C16A—C15A134.6 (2)
C4A—C5A—C6A—O3A176.65 (19)C12A—N2A—C16A—C15A50.1 (2)
O2A—C5A—C6A—C7A179.50 (19)C14A—C15A—C16A—N2A52.9 (3)
C4A—C5A—C6A—C7A0.1 (3)C14A—C15A—C16A—C17A73.7 (3)
C10B—O3B—C6B—C7B84.3 (3)C2B—N2B—C16B—C15B143.7 (2)
C10B—O3B—C6B—C5B95.7 (2)C12B—N2B—C16B—C15B44.8 (3)
O2B—C5B—C6B—O3B0.2 (3)C2B—N2B—C16B—C17B89.2 (2)
C4B—C5B—C6B—O3B179.3 (2)C12B—N2B—C16B—C17B82.3 (2)
O2B—C5B—C6B—C7B179.8 (2)C14B—C15B—C16B—N2B51.6 (3)
C4B—C5B—C6B—C7B0.7 (3)C14B—C15B—C16B—C17B74.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···S1Bi0.83 (2)2.84 (3)3.649 (2)167 (2)
N1B—H1B···S1Aii0.85 (2)2.48 (3)3.274 (2)156 (2)
Symmetry codes: (i) x+1, y+1, z; (ii) x1, y1, z.
 

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