PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): o2572–o2573.
Published online 2010 September 18. doi:  10.1107/S1600536810036226
PMCID: PMC2983284

3-Benzoyl-1,1-dibenzyl­thio­urea

Abstract

Two independent thio­urea mol­ecules comprise the asymmetric unit of the title compound, C22H20N2OS. The central N–C(=S)N(H)C(=O) atoms in each mol­ecule are virtually superimposable and each is twisted [C—N—C—S torsion angles = 121.3 (3) and −62.3 (4)°]. The mol­ecules differ only in terms of the relative orientations of the benzyl benzene rings [major difference between the C—N—C—C torsion angles of −146.6 (3) and −132.9 (3)°]. The presence of N—H(...)S hydrogen bonding leads to the formation of supra­molecular chains along the a axis. These are consolidated in the crystal packing by C—H(...)O inter­actions. The crystal was found to be a combined non-merohedral and racemic twin (twin law An external file that holds a picture, illustration, etc.
Object name is e-66-o2572-efi1.jpg00/0An external file that holds a picture, illustration, etc.
Object name is e-66-o2572-efi1.jpg0/001), with the fractional contribution of the minor components being approximately 9 and 28%.

Related literature

For our studies of thio­urea and its derivatives, see: Gunasekaran et al. (2010 [triangle]). For the biological activity of thio­urea derivatives, see: Venkatachalam et al. (2004 [triangle]); Yuan et al. (2001 [triangle]); Zhou et al. (2004 [triangle]). For additional geometric analysis, see: Spek (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2572-scheme1.jpg

Experimental

Crystal data

  • C22H20N2OS
  • M r = 360.46
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2572-efi3.jpg
  • a = 7.7338 (5) Å
  • b = 24.3478 (16) Å
  • c = 9.8593 (6) Å
  • β = 90.074 (1)°
  • V = 1856.5 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.19 mm−1
  • T = 100 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.946, T max = 0.982
  • 17536 measured reflections
  • 8469 independent reflections
  • 7807 reflections with I > 2σ(I)
  • R int = 0.055

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.157
  • S = 1.03
  • 8469 reflections
  • 470 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 1.27 e Å−3
  • Δρmin = −0.36 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 4101 Friedel pairs
  • Flack parameter: 0.25 (8)

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]), DIAMOND (Brandenburg, 2006 [triangle]) and Qmol (Gans & Shalloway, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810036226/lh5120sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036226/lh5120Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

NG thanks the NITT for a Fellowship. The authors also thank the University of Malaya for support of the crystallographic facility.

supplementary crystallographic information

Comment

The title compound, (I), was investigated in continuation of studies (Gunasekaran et al., 2010) of thiourea and its derivatives, which are useful as anti-tumour, anti-fungal, anti-bacterial, insecticidal, herbicidal, pesticidal agents, and plant-growth regulators (Venkatachalam et al., 2004; Yuan et al., 2001; Zhou et al., 2004).

Two independent molecules comprise the asymmetric unit of (I). The central N–C(═S)N(H)C(═O) atoms of the first independent molecule, Fig. 1, are virtually super-imposable upon those of the second, Fig. 2. The C7–N2–C8–S1 and C29–N4 –C30–N3 torsion angles of 121.3 (3) and -62.3 (4) °, respectively, indicate significant twists in the central part of each molecule. The major differences between the molecules relate to the orientations of the benzene rings as indicated in Fig. 3. The major conformational difference is quantified in the C8–N1–C9–C10 and C30–N3–C38–C39 torsion angles -146.6 (3) and -132.9 (3) °, respectively. The r.m.s. deviations for bond distances and angles are 0.0105 Å and 0.651 °, respectively (Spek, 2009).

The most notable feature in the crystal packing is the formation of supramolecular chains along the a axis mediated by N–H···S hydrogen bonding, Fig. 4 and Table 1. The chains pack in the ac plane and stack along the b axis with the primary connections along this axis being of the type C–H···O, Fig. 5 and Table 1.

Experimental

A solution of benzoyl chloride (0.7029 g, 5 mmol) in acetone (50 ml) was added drop wise to a suspension of potassium thiocyanate (0.4859 g, 5 mmol) in anhydrous acetone (50 ml). The reaction mixture was heated under reflux for 45 minutes and then cooled to room temperature. A solution of dibenzyl amine (0.9864 g, 5 mmol) in acetone (30 ml) was added and the resulting mixture was stirred for 2 h. Hydrochloric acid (0.1 N, 300 ml) was added and the resulting white solid was filtered, washed with water and dried in vacuo. Single crystals were grown at room temperature from its ethyl acetate solution by the diffusion of diethyl ether vapour. Yield 78%; M. Pt. 403 K; FT—IR (KBr) ν(N–H) 3239, ν(C═O) 1690, ν(C═S) 1314 cm-1.

Refinement

Carbon-bound H-atoms were placed in calculated positions (N–H = 0.86 Å and C–H = 0.95 to 0.99 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Uequiv(N, C). The maximum and minimum residual electron density peaks of 1.27 and 0.36 e Å-3, respectively, were located 1.65 Å and 0.89 Å from the H38a and S2 atoms, respectively. As the structure is a non-merohedral twin that belongs to a non-centric space group, the non-merohedral twinning and racemic twinning were treated in combination. The twin law -1 0 0 / 0 - 1 0 / 0 0 1 was used as the monoclinic unit cell emulated an orthorhombic unit cell. The Flack parameter refined to 0.25 (8).

Figures

Fig. 1.
The molecular structure of the first independent molecule in (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
Fig. 2.
The molecular structure of the second independent molecule in (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
Fig. 3.
Overlay diagram of the first independent molecule (shown in red) and the second independent molecule (shown in blue).
Fig. 4.
Linear supramolecular chain along the a axis in (I) mediated by N–H···S hydrogen bonding, shown as blue dashed lines.
Fig. 5.
Unit-cell contents shown in projection down the c axis in (I). The N–H···S hydrogen bonding and C–H···O contacts are shown as blue and orange dashed lines, respectively.

Crystal data

C22H20N2OSF(000) = 760
Mr = 360.46Dx = 1.290 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 6510 reflections
a = 7.7338 (5) Åθ = 2.2–28.1°
b = 24.3478 (16) ŵ = 0.19 mm1
c = 9.8593 (6) ÅT = 100 K
β = 90.074 (1)°Block, colourless
V = 1856.5 (2) Å30.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer8469 independent reflections
Radiation source: fine-focus sealed tube7807 reflections with I > 2σ(I)
graphiteRint = 0.055
ω scansθmax = 27.5°, θmin = 0.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.946, Tmax = 0.982k = −31→31
17536 measured reflectionsl = −12→11

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.157w = 1/[σ2(Fo2) + (0.0934P)2 + 0.2767P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
8469 reflectionsΔρmax = 1.27 e Å3
470 parametersΔρmin = −0.36 e Å3
1 restraintAbsolute structure: Flack (1983), 4101 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.25 (8)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S11.52015 (10)0.49995 (3)0.21954 (8)0.01637 (17)
S21.02727 (11)0.46914 (3)0.10081 (9)0.01665 (17)
O11.3589 (3)0.66362 (10)0.2194 (3)0.0228 (6)
O20.8629 (3)0.30856 (10)0.0894 (3)0.0239 (6)
N11.5083 (4)0.58006 (11)0.0339 (3)0.0157 (6)
N21.2782 (4)0.57501 (10)0.1861 (3)0.0140 (5)
H21.19110.55310.18430.017*
N31.0001 (4)0.38816 (12)0.2845 (3)0.0179 (6)
N40.7766 (4)0.39659 (11)0.1265 (3)0.0162 (6)
H40.68990.41870.12770.019*
C11.0820 (4)0.63713 (13)0.3027 (3)0.0154 (6)
C20.9587 (5)0.59635 (14)0.3240 (4)0.0204 (7)
H2A0.98220.55970.29690.024*
C30.8020 (5)0.60887 (16)0.3846 (4)0.0242 (8)
H30.71830.58090.39860.029*
C40.7672 (5)0.66233 (15)0.4247 (4)0.0239 (8)
H4A0.66010.67080.46680.029*
C50.8880 (5)0.70339 (15)0.4038 (4)0.0240 (8)
H50.86350.74000.43100.029*
C61.0446 (5)0.69113 (14)0.3431 (4)0.0208 (7)
H61.12730.71940.32870.025*
C71.2514 (4)0.62775 (13)0.2336 (3)0.0151 (6)
C81.4372 (4)0.55502 (13)0.1409 (3)0.0139 (6)
C91.6810 (4)0.56209 (14)−0.0142 (4)0.0195 (7)
H9A1.66540.5336−0.08490.023*
H9B1.74410.54510.06240.023*
C101.7895 (4)0.60781 (13)−0.0715 (4)0.0176 (7)
C111.8660 (5)0.60174 (15)−0.1997 (4)0.0214 (7)
H111.84240.5700−0.25270.026*
C121.9766 (5)0.64222 (16)−0.2494 (4)0.0234 (8)
H122.02860.6380−0.33600.028*
C132.0104 (5)0.68838 (16)−0.1727 (4)0.0252 (8)
H132.08560.7159−0.20690.030*
C141.9355 (5)0.69483 (16)−0.0462 (4)0.0272 (8)
H141.96000.72670.00590.033*
C151.8248 (5)0.65500 (15)0.0050 (4)0.0242 (8)
H151.77310.65980.09160.029*
C161.4092 (5)0.61491 (14)−0.0616 (3)0.0178 (7)
H16A1.47510.6489−0.08100.021*
H16B1.29780.6255−0.01970.021*
C171.3751 (4)0.58415 (14)−0.1933 (3)0.0163 (6)
C181.4287 (4)0.60578 (15)−0.3151 (4)0.0201 (7)
H181.49290.6390−0.31660.024*
C191.3891 (5)0.57905 (16)−0.4367 (4)0.0224 (7)
H191.42470.5944−0.52070.027*
C201.2973 (5)0.52985 (17)−0.4347 (4)0.0265 (8)
H201.27040.5115−0.51710.032*
C211.2453 (5)0.50774 (16)−0.3114 (4)0.0280 (8)
H211.18330.4741−0.30980.034*
C221.2830 (5)0.53436 (15)−0.1908 (4)0.0235 (8)
H221.24680.5191−0.10680.028*
C230.5896 (4)0.33461 (14)−0.0012 (3)0.0152 (6)
C240.5720 (5)0.28392 (14)−0.0668 (4)0.0208 (7)
H240.66190.2574−0.06070.025*
C250.4246 (5)0.27233 (15)−0.1403 (4)0.0237 (8)
H250.41450.2383−0.18690.028*
C260.2900 (5)0.31064 (17)−0.1465 (4)0.0279 (9)
H260.18650.3019−0.19380.033*
C270.3071 (5)0.36096 (15)−0.0840 (4)0.0240 (8)
H270.21740.3875−0.09110.029*
C280.4566 (4)0.37286 (14)−0.0104 (4)0.0196 (7)
H280.46770.40740.03370.024*
C290.7538 (4)0.34428 (14)0.0742 (3)0.0158 (6)
C300.9368 (4)0.41485 (13)0.1778 (3)0.0153 (6)
C310.8927 (5)0.35268 (14)0.3720 (4)0.0208 (7)
H31A0.95260.31730.38780.025*
H31B0.78120.34490.32650.025*
C320.8599 (5)0.38108 (14)0.5071 (3)0.0182 (7)
C330.9196 (5)0.35777 (15)0.6274 (4)0.0199 (7)
H330.98310.32440.62510.024*
C340.8866 (5)0.38311 (16)0.7499 (4)0.0221 (7)
H340.92600.36680.83190.026*
C350.7964 (5)0.43216 (16)0.7538 (4)0.0246 (8)
H350.77490.44970.83820.030*
C360.7367 (5)0.45597 (15)0.6329 (4)0.0263 (8)
H360.67380.48950.63510.032*
C370.7702 (5)0.43033 (16)0.5101 (4)0.0271 (8)
H370.73150.44660.42780.033*
C381.1725 (5)0.40062 (15)0.3372 (4)0.0230 (8)
H38A1.16070.42160.42270.028*
H38B1.23390.42420.27120.028*
C391.2794 (5)0.35003 (15)0.3639 (4)0.0212 (7)
C401.3815 (5)0.34745 (16)0.4800 (4)0.0244 (8)
H401.37630.37600.54570.029*
C411.4926 (5)0.30219 (17)0.4997 (5)0.0304 (9)
H411.56180.30010.57930.036*
C421.5013 (5)0.26096 (16)0.4041 (4)0.0288 (9)
H421.57890.23110.41670.035*
C431.3972 (6)0.26289 (17)0.2894 (5)0.0308 (9)
H431.40200.23410.22460.037*
C441.2852 (5)0.30727 (16)0.2692 (4)0.0255 (8)
H441.21300.30840.19120.031*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0164 (4)0.0154 (4)0.0173 (4)0.0015 (3)−0.0008 (3)0.0026 (3)
S20.0153 (4)0.0147 (4)0.0199 (4)−0.0025 (3)0.0031 (3)0.0014 (3)
O10.0184 (12)0.0191 (12)0.0310 (15)−0.0043 (10)0.0077 (11)−0.0040 (11)
O20.0204 (13)0.0205 (12)0.0309 (15)0.0037 (10)−0.0070 (11)−0.0070 (11)
N10.0158 (14)0.0158 (13)0.0154 (14)0.0053 (11)0.0039 (11)0.0037 (10)
N20.0145 (13)0.0118 (12)0.0157 (14)−0.0011 (10)0.0029 (11)−0.0022 (10)
N30.0171 (14)0.0161 (13)0.0206 (15)−0.0071 (11)−0.0011 (12)0.0006 (11)
N40.0141 (13)0.0154 (13)0.0191 (14)−0.0001 (10)0.0016 (11)−0.0022 (11)
C10.0141 (15)0.0159 (15)0.0162 (16)0.0013 (12)−0.0003 (12)−0.0014 (12)
C20.0191 (17)0.0161 (16)0.0259 (19)−0.0012 (13)0.0042 (14)−0.0053 (13)
C30.0165 (17)0.0258 (18)0.030 (2)−0.0058 (14)0.0078 (15)−0.0075 (15)
C40.0172 (17)0.0254 (18)0.029 (2)0.0016 (14)0.0050 (15)−0.0027 (15)
C50.027 (2)0.0170 (17)0.027 (2)0.0042 (14)0.0069 (16)−0.0024 (14)
C60.0264 (19)0.0152 (16)0.0209 (18)−0.0008 (13)0.0076 (14)−0.0031 (13)
C70.0164 (16)0.0163 (15)0.0125 (15)0.0004 (12)−0.0008 (12)0.0005 (12)
C80.0109 (14)0.0167 (15)0.0141 (15)−0.0023 (12)−0.0017 (12)−0.0025 (12)
C90.0160 (16)0.0184 (16)0.0242 (18)0.0031 (13)0.0087 (14)0.0039 (14)
C100.0139 (15)0.0160 (15)0.0228 (18)−0.0004 (12)0.0015 (13)0.0021 (13)
C110.0162 (16)0.0210 (17)0.0271 (19)−0.0009 (13)0.0072 (14)0.0023 (14)
C120.0160 (16)0.0312 (19)0.0231 (19)0.0009 (14)0.0057 (14)0.0039 (15)
C130.0193 (18)0.0255 (18)0.031 (2)−0.0004 (14)0.0003 (15)0.0101 (16)
C140.031 (2)0.0213 (18)0.029 (2)−0.0020 (15)−0.0030 (16)0.0002 (15)
C150.030 (2)0.0186 (17)0.0242 (19)−0.0007 (14)0.0005 (15)0.0011 (14)
C160.0190 (16)0.0179 (15)0.0163 (16)0.0058 (12)0.0048 (13)0.0052 (13)
C170.0130 (15)0.0192 (15)0.0166 (16)0.0035 (12)0.0004 (12)0.0034 (13)
C180.0195 (17)0.0227 (17)0.0180 (17)−0.0022 (13)−0.0012 (13)0.0027 (14)
C190.0211 (18)0.032 (2)0.0141 (17)−0.0012 (15)0.0003 (14)0.0044 (14)
C200.0238 (19)0.031 (2)0.0248 (19)−0.0036 (15)−0.0021 (15)−0.0018 (16)
C210.031 (2)0.0244 (19)0.029 (2)−0.0068 (15)−0.0015 (16)0.0006 (15)
C220.0289 (19)0.0224 (17)0.0192 (18)−0.0051 (15)0.0052 (15)0.0039 (14)
C230.0145 (15)0.0179 (15)0.0132 (15)−0.0013 (12)0.0003 (12)−0.0014 (12)
C240.0203 (18)0.0170 (16)0.0252 (19)−0.0012 (13)−0.0008 (15)−0.0043 (14)
C250.0228 (18)0.0198 (17)0.028 (2)−0.0004 (14)−0.0053 (15)−0.0087 (15)
C260.0183 (18)0.0298 (19)0.036 (2)−0.0001 (15)−0.0116 (16)−0.0074 (17)
C270.0180 (18)0.0263 (19)0.028 (2)0.0045 (14)−0.0039 (15)−0.0032 (15)
C280.0181 (17)0.0207 (16)0.0199 (17)0.0000 (13)−0.0019 (14)−0.0019 (13)
C290.0175 (16)0.0178 (15)0.0121 (15)0.0004 (12)0.0002 (12)0.0000 (12)
C300.0155 (15)0.0130 (14)0.0172 (16)−0.0015 (12)0.0033 (12)−0.0041 (12)
C310.0266 (18)0.0189 (16)0.0170 (17)−0.0093 (14)0.0004 (14)0.0010 (13)
C320.0219 (17)0.0185 (16)0.0142 (16)−0.0085 (13)0.0002 (13)−0.0008 (13)
C330.0189 (17)0.0204 (17)0.0204 (18)−0.0023 (13)−0.0012 (13)0.0030 (13)
C340.0172 (17)0.0334 (19)0.0156 (17)0.0018 (14)−0.0013 (13)0.0018 (15)
C350.0258 (19)0.029 (2)0.0187 (18)−0.0012 (15)−0.0002 (15)−0.0018 (15)
C360.027 (2)0.0238 (19)0.028 (2)0.0093 (15)−0.0025 (16)−0.0043 (15)
C370.027 (2)0.0275 (19)0.027 (2)−0.0015 (15)−0.0071 (16)0.0053 (16)
C380.0217 (17)0.0205 (17)0.027 (2)−0.0067 (14)−0.0072 (15)−0.0003 (14)
C390.0210 (18)0.0235 (17)0.0190 (17)−0.0059 (14)−0.0022 (14)0.0027 (14)
C400.0188 (18)0.0309 (19)0.0234 (19)−0.0093 (15)−0.0040 (14)0.0052 (15)
C410.0180 (18)0.036 (2)0.037 (2)−0.0102 (16)−0.0069 (16)0.0093 (17)
C420.0201 (18)0.0238 (18)0.043 (2)−0.0037 (15)0.0075 (17)0.0078 (16)
C430.034 (2)0.0236 (19)0.035 (2)0.0015 (17)0.0039 (18)−0.0001 (16)
C440.031 (2)0.0240 (18)0.0214 (19)−0.0031 (15)−0.0013 (15)−0.0002 (15)

Geometric parameters (Å, °)

S1—C81.676 (3)C18—H180.9500
S2—C301.678 (3)C19—C201.393 (5)
O1—C71.214 (4)C19—H190.9500
O2—C291.221 (4)C20—C211.390 (6)
N1—C81.337 (4)C20—H200.9500
N1—C161.480 (4)C21—C221.385 (5)
N1—C91.484 (4)C21—H210.9500
N2—C71.382 (4)C22—H220.9500
N2—C81.396 (4)C23—C281.390 (5)
N2—H20.8600C23—C241.400 (5)
N3—C301.329 (4)C23—C291.489 (5)
N3—C381.462 (4)C24—C251.380 (5)
N3—C311.477 (4)C24—H240.9500
N4—C291.386 (4)C25—C261.399 (5)
N4—C301.410 (4)C25—H250.9500
N4—H40.8600C26—C271.378 (5)
C1—C21.393 (5)C26—H260.9500
C1—C61.404 (5)C27—C281.395 (5)
C1—C71.495 (5)C27—H270.9500
C2—C31.386 (5)C28—H280.9500
C2—H2A0.9500C31—C321.522 (5)
C3—C41.387 (5)C31—H31A0.9900
C3—H30.9500C31—H31B0.9900
C4—C51.384 (5)C32—C371.386 (5)
C4—H4A0.9500C32—C331.393 (5)
C5—C61.384 (5)C33—C341.381 (5)
C5—H50.9500C33—H330.9500
C6—H60.9500C34—C351.384 (5)
C9—C101.504 (5)C34—H340.9500
C9—H9A0.9900C35—C361.403 (5)
C9—H9B0.9900C35—H350.9500
C10—C151.401 (5)C36—C371.387 (6)
C10—C111.405 (5)C36—H360.9500
C11—C121.394 (5)C37—H370.9500
C11—H110.9500C38—C391.507 (5)
C12—C131.379 (6)C38—H38A0.9900
C12—H120.9500C38—H38B0.9900
C13—C141.384 (6)C39—C401.391 (5)
C13—H130.9500C39—C441.399 (5)
C14—C151.389 (5)C40—C411.411 (6)
C14—H140.9500C40—H400.9500
C15—H150.9500C41—C421.379 (6)
C16—C171.522 (5)C41—H410.9500
C16—H16A0.9900C42—C431.388 (6)
C16—H16B0.9900C42—H420.9500
C17—C181.376 (5)C43—C441.399 (6)
C17—C221.406 (5)C43—H430.9500
C18—C191.398 (5)C44—H440.9500
C8—N1—C16123.3 (3)C22—C21—C20120.6 (3)
C8—N1—C9119.3 (3)C22—C21—H21119.7
C16—N1—C9115.5 (3)C20—C21—H21119.7
C7—N2—C8124.4 (3)C21—C22—C17119.6 (3)
C7—N2—H2117.8C21—C22—H22120.2
C8—N2—H2117.8C17—C22—H22120.2
C30—N3—C38121.0 (3)C28—C23—C24119.3 (3)
C30—N3—C31122.8 (3)C28—C23—C29123.9 (3)
C38—N3—C31115.3 (3)C24—C23—C29116.9 (3)
C29—N4—C30122.3 (3)C25—C24—C23120.2 (3)
C29—N4—H4118.8C25—C24—H24119.9
C30—N4—H4118.8C23—C24—H24119.9
C2—C1—C6118.9 (3)C24—C25—C26120.1 (3)
C2—C1—C7124.1 (3)C24—C25—H25120.0
C6—C1—C7117.0 (3)C26—C25—H25120.0
C3—C2—C1120.5 (3)C27—C26—C25120.2 (3)
C3—C2—H2A119.8C27—C26—H26119.9
C1—C2—H2A119.8C25—C26—H26119.9
C2—C3—C4119.9 (3)C26—C27—C28119.8 (3)
C2—C3—H3120.0C26—C27—H27120.1
C4—C3—H3120.0C28—C27—H27120.1
C5—C4—C3120.3 (3)C23—C28—C27120.5 (3)
C5—C4—H4A119.9C23—C28—H28119.7
C3—C4—H4A119.9C27—C28—H28119.7
C6—C5—C4120.0 (3)O2—C29—N4121.4 (3)
C6—C5—H5120.0O2—C29—C23122.5 (3)
C4—C5—H5120.0N4—C29—C23116.1 (3)
C5—C6—C1120.3 (3)N3—C30—N4116.9 (3)
C5—C6—H6119.8N3—C30—S2126.2 (2)
C1—C6—H6119.8N4—C30—S2116.9 (3)
O1—C7—N2121.7 (3)N3—C31—C32109.9 (3)
O1—C7—C1122.9 (3)N3—C31—H31A109.7
N2—C7—C1115.4 (3)C32—C31—H31A109.7
N1—C8—N2117.1 (3)N3—C31—H31B109.7
N1—C8—S1124.9 (3)C32—C31—H31B109.7
N2—C8—S1117.9 (2)H31A—C31—H31B108.2
N1—C9—C10113.8 (3)C37—C32—C33120.0 (3)
N1—C9—H9A108.8C37—C32—C31119.7 (3)
C10—C9—H9A108.8C33—C32—C31120.3 (3)
N1—C9—H9B108.8C34—C33—C32120.1 (3)
C10—C9—H9B108.8C34—C33—H33119.9
H9A—C9—H9B107.7C32—C33—H33119.9
C15—C10—C11119.3 (3)C33—C34—C35120.2 (3)
C15—C10—C9120.9 (3)C33—C34—H34119.9
C11—C10—C9119.7 (3)C35—C34—H34119.9
C12—C11—C10120.1 (3)C34—C35—C36119.9 (3)
C12—C11—H11120.0C34—C35—H35120.1
C10—C11—H11120.0C36—C35—H35120.1
C13—C12—C11120.0 (4)C37—C36—C35119.6 (3)
C13—C12—H12120.0C37—C36—H36120.2
C11—C12—H12120.0C35—C36—H36120.2
C12—C13—C14120.4 (4)C32—C37—C36120.1 (4)
C12—C13—H13119.8C32—C37—H37119.9
C14—C13—H13119.8C36—C37—H37119.9
C13—C14—C15120.5 (4)N3—C38—C39113.1 (3)
C13—C14—H14119.8N3—C38—H38A109.0
C15—C14—H14119.8C39—C38—H38A109.0
C14—C15—C10119.8 (4)N3—C38—H38B109.0
C14—C15—H15120.1C39—C38—H38B109.0
C10—C15—H15120.1H38A—C38—H38B107.8
N1—C16—C17110.5 (3)C40—C39—C44119.8 (4)
N1—C16—H16A109.6C40—C39—C38119.4 (3)
C17—C16—H16A109.6C44—C39—C38120.7 (3)
N1—C16—H16B109.6C39—C40—C41119.6 (4)
C17—C16—H16B109.6C39—C40—H40120.2
H16A—C16—H16B108.1C41—C40—H40120.2
C18—C17—C22119.9 (3)C42—C41—C40120.3 (4)
C18—C17—C16120.3 (3)C42—C41—H41119.8
C22—C17—C16119.7 (3)C40—C41—H41119.8
C17—C18—C19120.3 (3)C41—C42—C43120.2 (4)
C17—C18—H18119.8C41—C42—H42119.9
C19—C18—H18119.8C43—C42—H42119.9
C20—C19—C18119.9 (3)C42—C43—C44120.0 (4)
C20—C19—H19120.0C42—C43—H43120.0
C18—C19—H19120.0C44—C43—H43120.0
C21—C20—C19119.6 (4)C43—C44—C39120.0 (4)
C21—C20—H20120.2C43—C44—H44120.0
C19—C20—H20120.2C39—C44—H44120.0
C6—C1—C2—C3−0.2 (5)C28—C23—C24—C250.3 (5)
C7—C1—C2—C3−177.6 (3)C29—C23—C24—C25−179.0 (3)
C1—C2—C3—C4−0.2 (6)C23—C24—C25—C26−1.8 (6)
C2—C3—C4—C50.5 (6)C24—C25—C26—C272.8 (7)
C3—C4—C5—C6−0.3 (6)C25—C26—C27—C28−2.3 (6)
C4—C5—C6—C1−0.1 (6)C24—C23—C28—C270.1 (5)
C2—C1—C6—C50.4 (5)C29—C23—C28—C27179.4 (3)
C7—C1—C6—C5177.9 (3)C26—C27—C28—C230.9 (6)
C8—N2—C7—O112.0 (5)C30—N4—C29—O211.8 (5)
C8—N2—C7—C1−168.0 (3)C30—N4—C29—C23−168.1 (3)
C2—C1—C7—O1−178.0 (3)C28—C23—C29—O2174.3 (3)
C6—C1—C7—O14.6 (5)C24—C23—C29—O2−6.4 (5)
C2—C1—C7—N22.1 (5)C28—C23—C29—N4−5.8 (5)
C6—C1—C7—N2−175.3 (3)C24—C23—C29—N4173.5 (3)
C16—N1—C8—N2−19.0 (5)C38—N3—C30—N4174.2 (3)
C9—N1—C8—N2177.2 (3)C31—N3—C30—N4−17.7 (5)
C16—N1—C8—S1158.1 (3)C38—N3—C30—S2−7.3 (5)
C9—N1—C8—S1−5.7 (5)C31—N3—C30—S2160.7 (3)
C7—N2—C8—N1−61.4 (4)C29—N4—C30—N3−62.3 (4)
C7—N2—C8—S1121.3 (3)C29—N4—C30—S2119.1 (3)
C8—N1—C9—C10−146.6 (3)C30—N3—C31—C32−106.5 (4)
C16—N1—C9—C1048.4 (4)C38—N3—C31—C3262.2 (4)
N1—C9—C10—C1555.3 (5)N3—C31—C32—C3762.2 (4)
N1—C9—C10—C11−128.9 (3)N3—C31—C32—C33−117.7 (3)
C15—C10—C11—C120.4 (5)C37—C32—C33—C341.3 (5)
C9—C10—C11—C12−175.5 (3)C31—C32—C33—C34−178.8 (3)
C10—C11—C12—C13−0.2 (5)C32—C33—C34—C35−1.0 (5)
C11—C12—C13—C140.1 (6)C33—C34—C35—C360.6 (6)
C12—C13—C14—C15−0.2 (6)C34—C35—C36—C37−0.6 (6)
C13—C14—C15—C100.4 (6)C33—C32—C37—C36−1.3 (6)
C11—C10—C15—C14−0.5 (5)C31—C32—C37—C36178.8 (4)
C9—C10—C15—C14175.3 (3)C35—C36—C37—C320.9 (6)
C8—N1—C16—C17−103.7 (4)C30—N3—C38—C39−132.9 (3)
C9—N1—C16—C1760.7 (4)C31—N3—C38—C3958.2 (4)
N1—C16—C17—C18−123.1 (3)N3—C38—C39—C40−139.2 (3)
N1—C16—C17—C2259.2 (4)N3—C38—C39—C4444.8 (5)
C22—C17—C18—C191.2 (5)C44—C39—C40—C411.3 (5)
C16—C17—C18—C19−176.5 (3)C38—C39—C40—C41−174.8 (3)
C17—C18—C19—C20−1.0 (5)C39—C40—C41—C420.5 (6)
C18—C19—C20—C210.2 (6)C40—C41—C42—C43−1.8 (6)
C19—C20—C21—C220.4 (6)C41—C42—C43—C441.2 (6)
C20—C21—C22—C17−0.2 (6)C42—C43—C44—C390.7 (6)
C18—C17—C22—C21−0.7 (5)C40—C39—C44—C43−1.9 (6)
C16—C17—C22—C21177.1 (3)C38—C39—C44—C43174.1 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···S20.862.543.334 (3)154
N4—H4···S1i0.862.543.334 (3)154
C13—H13···O2ii0.952.573.193 (5)124
C14—H14···O2ii0.952.603.207 (5)122
C25—H25···O1iii0.952.553.228 (4)129

Symmetry codes: (i) x−1, y, z; (ii) −x+3, y+1/2, −z; (iii) −x+2, y−1/2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5120).

References

  • Brandenburg, K. (2006). DIAMOND Crystal Impact GbR, Bonn, Germany.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model 19, 557–559. [PubMed]
  • Gunasekaran, N., Karvembu, R., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2113. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Venkatachalam, T. K., Mao, C. & Uckun, F. M. (2004). Bioorg. Med. Chem 12, 4275–4284. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.
  • Yuan, Y. F., Wang, J. T., Gimeno, M. C., Laguna, A. & Jones, P. G. (2001). Inorg. Chim. Acta, 324, 309–317.
  • Zhou, W. Q., Li, B. L., Zhu, L. M., Ding, J. G., Yong, Z., Lu, L. & Yang, X. J. (2004). J. Mol. Struct 690, 145–150.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography