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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2835.
Published online 2010 October 20. doi:  10.1107/S1600536810040730
PMCID: PMC3009160

5,5′,5′′-Triphenyl-2,2′,2′′-[2,4,6-tri­methyl­benzene-1,3,5-triyltris(methyl­idene­sulfanedi­yl)]tris­(1,3,4-oxadiazole)

Abstract

In the title compound, C36H30N6O3S3, the phenyl rings are twisted from the attached oxadiazole rings in the three arms by 1.5(2), 2.4 (2) and 25.7 (2)°. The crystal packing exhibits weak inter­molecular C—H(...)N inter­actions.

Related literature

For general background to 1,3,4-oxadiazole derivatives, see Al-Talib et al. (1990 [triangle]); Wang et al. (2005 [triangle]) and to thio-based ligands with a multi-armed tripodal geometry, see: PrakashaReddy & Pedireddi (2007 [triangle]). For the crystal structure of an Ag complex with a related oxadiazole derivative, see: Zhang et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2835-scheme1.jpg

Experimental

Crystal data

  • C36H30N6O3S3
  • M r = 690.84
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2835-efi1.jpg
  • a = 19.870 (4) Å
  • b = 9.1305 (18) Å
  • c = 18.557 (4) Å
  • β = 107.00 (3)°
  • V = 3219.6 (11) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.28 mm−1
  • T = 113 K
  • 0.22 × 0.20 × 0.10 mm

Data collection

  • Rigaku Saturn CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 1999 [triangle]) T min = 0.941, T max = 0.973
  • 23119 measured reflections
  • 5664 independent reflections
  • 4490 reflections with I > 2σ(I)
  • R int = 0.051

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.149
  • S = 1.10
  • 5664 reflections
  • 437 parameters
  • H-atom parameters constrained
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.37 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 1999 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040730/cv2772sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040730/cv2772Isup2.hkl

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

Acknowledgments

Financial support from the Key Laboratory Project of Liaoning Province (grant No. 2008S127) and from the doctoral starting Foundation of Liaoning Province (grant No. 20071103) is gratefully acknowledged.

supplementary crystallographic information

Comment

1,3,4-Oxadiazole derivatives have wide applications in medicine, industry and coordination chemistry, so they are under intensive studies (Al-Talib et al., 1990; Wang et al., 2005; Zhang et al., 2007). Recently, novel thio-based ligands with multi-armed tripodal geometry were synthesized, and these ligands demonstrated their significance in the supramolecular studies (PrakashaReddy & Pedireddi, 2007 and references therein). Herewith we present the title compound (I), where the 2,4,6-trimethylbenzene center contains three 5-phenyl-1,3,4-oxadiazol-2-ylsulfanylmethyl arms.

In (I) (Fig.1), two phenyloxadiazole fragments - C10—C15/C8/C9/N1/N2/O1 (A) and C20—C25/C18/C19/N3/N4/O2 (B), respectively - are situated on the one side of the central benzene ring (C1—C6), while the third phenyloxadiazole fragment - C30—C35/C28/C29/N5/N6/O3 (C) - is situated on the other side of the central benzene ring. In A and B, the oxadiazole rings are almost coplanar with the attached phenyl rings forming dihedral angles of 1.5 (2) and 2.4 (2)°, respectively. The terminal phenyl rings are roughly orthogonal to the plane of the central benzene ring with dihedral angles of 82.0 (2), 89.2 (2) and 72.4 (2)°, respectively. The crystal packing exhibits weak intermolecular C—H···N interactions (Table 1).

Experimental

A suspension of 5-phenyl-1,3,4-oxadiazole-2-thiol (3.0 mmol) and 2,4,6-trimethyl-1,3,5-tribromomethyl benzene (1.0 mmol) in ethanol (10 ml) was stirred at room temperature. The reaction progress was monitored via TLC. The resulting precipitate was filtered off, washed with cold ethanol, dried and purified to give the target product as white solid in 80% yield. Crystals of (I) suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform-ethanol (1:1).

Refinement

All H atoms were positioned geometrically and refined as riding (C—H = 0.95–0.99 Å) and allowed to ride on their parent atoms, with Uiso(H) =1.2-1.5Ueq of the parent atom.

Figures

Fig. 1.
View of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C36H30N6O3S3F(000) = 1440
Mr = 690.84Dx = 1.425 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7164 reflections
a = 19.870 (4) Åθ = 2.1–27.9°
b = 9.1305 (18) ŵ = 0.28 mm1
c = 18.557 (4) ÅT = 113 K
β = 107.00 (3)°Prism, colourless
V = 3219.6 (11) Å30.22 × 0.20 × 0.10 mm
Z = 4

Data collection

Rigaku Saturn CCD area-detector diffractometer5664 independent reflections
Radiation source: rotating anode4490 reflections with I > 2σ(I)
confocalRint = 0.051
Detector resolution: 7.31 pixels mm-1θmax = 25.0°, θmin = 2.1°
[var phi] and ω scansh = −23→19
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 1999)k = −10→10
Tmin = 0.941, Tmax = 0.973l = −19→22
23119 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.149w = 1/[σ2(Fo2) + (0.0804P)2 + 0.7757P] where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
5664 reflectionsΔρmax = 0.35 e Å3
437 parametersΔρmin = −0.37 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0130 (11)

Special details

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)

xyzUiso*/Ueq
S10.18609 (4)0.29928 (8)0.04709 (4)0.0293 (2)
S20.17834 (4)0.61632 (8)0.36748 (4)0.0305 (2)
S30.30065 (4)0.98854 (9)0.09276 (5)0.0366 (3)
O10.24745 (9)0.2057 (2)−0.05257 (11)0.0242 (5)
O20.12205 (9)0.6002 (2)0.47942 (11)0.0260 (5)
O30.37150 (9)1.2260 (2)0.08047 (11)0.0274 (5)
N10.16166 (13)0.3621 (3)−0.10346 (15)0.0361 (6)
N20.19355 (13)0.3179 (3)−0.15899 (14)0.0337 (6)
N30.06871 (12)0.7678 (3)0.39516 (14)0.0282 (6)
N40.03554 (12)0.7624 (3)0.45304 (14)0.0278 (6)
N50.43389 (12)1.0801 (3)0.17101 (15)0.0350 (6)
N60.47315 (13)1.2090 (3)0.16849 (16)0.0370 (7)
C10.17176 (14)0.5716 (3)0.10460 (16)0.0237 (6)
C20.14838 (14)0.5860 (3)0.16842 (16)0.0255 (6)
C30.17930 (14)0.6912 (3)0.22331 (16)0.0249 (6)
C40.23874 (15)0.7703 (3)0.21951 (17)0.0276 (7)
C50.26506 (14)0.7483 (3)0.15825 (17)0.0255 (6)
C60.23050 (14)0.6535 (3)0.09961 (16)0.0255 (6)
C70.13485 (14)0.4691 (3)0.04168 (17)0.0279 (7)
H7A0.12920.5173−0.00750.033*
H7B0.08740.44550.04560.033*
C80.19554 (14)0.2940 (3)−0.04264 (17)0.0263 (7)
C90.24297 (14)0.2274 (3)−0.12660 (16)0.0256 (6)
C100.29139 (14)0.1506 (3)−0.15903 (16)0.0250 (6)
C110.28586 (15)0.1687 (3)−0.23545 (17)0.0288 (7)
H110.25130.2328−0.26560.035*
C120.33012 (15)0.0942 (3)−0.26695 (18)0.0314 (7)
H120.32590.1061−0.31900.038*
C130.38190 (15)0.0000 (3)−0.22227 (19)0.0320 (7)
H130.4130−0.0509−0.24390.038*
C140.38718 (15)−0.0176 (3)−0.14763 (19)0.0324 (7)
H140.4221−0.0812−0.11760.039*
C150.34215 (14)0.0562 (3)−0.11523 (17)0.0300 (7)
H150.34600.0424−0.06340.036*
C160.08921 (16)0.4894 (4)0.17749 (18)0.0348 (7)
H16A0.04380.53550.15250.052*
H16B0.09400.47680.23120.052*
H16C0.09160.39360.15460.052*
C170.14338 (15)0.7269 (3)0.28308 (16)0.0281 (7)
H17A0.09220.70890.26250.034*
H17B0.15030.83190.29650.034*
C180.11798 (14)0.6706 (3)0.41349 (16)0.0254 (6)
C190.06834 (13)0.6633 (3)0.50062 (16)0.0245 (6)
C200.05478 (14)0.6132 (3)0.56941 (17)0.0254 (6)
C21−0.00131 (14)0.6715 (3)0.59100 (17)0.0298 (7)
H21−0.03130.74310.56060.036*
C22−0.01283 (15)0.6236 (4)0.65760 (18)0.0346 (8)
H22−0.05060.66330.67300.042*
C230.03049 (15)0.5184 (4)0.70162 (18)0.0341 (8)
H230.02230.48600.74700.041*
C240.08569 (16)0.4605 (3)0.67948 (17)0.0327 (7)
H240.11500.38750.70940.039*
C250.09819 (15)0.5085 (3)0.61421 (17)0.0303 (7)
H250.13670.46990.59980.036*
C260.27447 (18)0.8753 (4)0.2815 (2)0.0409 (8)
H26A0.32510.85530.29820.061*
H26B0.25510.86310.32400.061*
H26C0.26640.97600.26270.061*
C270.33018 (15)0.8295 (3)0.15422 (19)0.0318 (7)
H27A0.36000.76510.13340.038*
H27B0.35800.86170.20510.038*
C280.37511 (15)1.0980 (3)0.11886 (17)0.0287 (7)
C290.43512 (13)1.2908 (3)0.11594 (16)0.0257 (7)
C300.44873 (14)1.4375 (3)0.09273 (17)0.0274 (7)
C310.49555 (15)1.5280 (4)0.14417 (18)0.0338 (7)
H310.51911.49290.19320.041*
C320.50769 (17)1.6693 (4)0.1237 (2)0.0403 (8)
H320.53951.73100.15890.048*
C330.47366 (17)1.7209 (4)0.0524 (2)0.0418 (8)
H330.48161.81830.03890.050*
C340.42781 (16)1.6304 (4)0.0003 (2)0.0369 (8)
H340.40511.6652−0.04910.044*
C350.41525 (15)1.4894 (3)0.02058 (18)0.0315 (7)
H350.38371.4277−0.01490.038*
C360.25732 (16)0.6325 (3)0.03167 (18)0.0334 (7)
H36A0.28100.72210.02300.050*
H36B0.21760.6114−0.01280.050*
H36C0.29060.55060.04090.050*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0405 (4)0.0254 (4)0.0238 (4)0.0061 (3)0.0123 (3)0.0017 (3)
S20.0366 (4)0.0302 (5)0.0267 (4)0.0085 (3)0.0127 (3)0.0024 (3)
S30.0302 (4)0.0306 (5)0.0435 (5)−0.0040 (3)0.0020 (3)0.0140 (4)
O10.0283 (10)0.0238 (11)0.0189 (11)0.0006 (8)0.0043 (8)−0.0021 (8)
O20.0278 (10)0.0296 (12)0.0215 (11)0.0002 (8)0.0084 (8)−0.0016 (9)
O30.0252 (10)0.0298 (12)0.0241 (11)−0.0036 (8)0.0022 (8)0.0055 (9)
N10.0448 (15)0.0405 (16)0.0248 (15)0.0129 (12)0.0130 (12)0.0037 (12)
N20.0395 (14)0.0385 (16)0.0229 (15)0.0066 (12)0.0090 (11)0.0008 (12)
N30.0298 (13)0.0302 (14)0.0271 (14)0.0007 (11)0.0119 (11)0.0008 (11)
N40.0277 (12)0.0319 (14)0.0260 (14)−0.0018 (10)0.0115 (11)−0.0036 (11)
N50.0285 (13)0.0358 (15)0.0357 (16)−0.0010 (11)0.0016 (11)0.0076 (12)
N60.0297 (13)0.0354 (16)0.0393 (17)−0.0042 (11)−0.0002 (12)0.0057 (13)
C10.0279 (14)0.0201 (15)0.0227 (16)0.0079 (11)0.0067 (12)0.0022 (12)
C20.0277 (14)0.0237 (15)0.0257 (16)0.0065 (12)0.0086 (12)0.0074 (13)
C30.0317 (15)0.0202 (15)0.0232 (16)0.0068 (12)0.0088 (12)0.0009 (12)
C40.0338 (16)0.0207 (15)0.0291 (17)0.0035 (12)0.0105 (13)0.0036 (12)
C50.0276 (15)0.0192 (15)0.0304 (17)0.0051 (11)0.0092 (12)0.0086 (12)
C60.0324 (15)0.0224 (15)0.0230 (16)0.0095 (12)0.0099 (12)0.0084 (12)
C70.0286 (15)0.0305 (17)0.0233 (16)0.0060 (12)0.0057 (12)0.0004 (13)
C80.0304 (15)0.0214 (15)0.0270 (17)0.0016 (12)0.0081 (12)−0.0017 (12)
C90.0300 (15)0.0259 (16)0.0184 (16)−0.0019 (12)0.0035 (12)0.0032 (12)
C100.0285 (15)0.0249 (16)0.0241 (16)−0.0069 (12)0.0114 (12)−0.0028 (12)
C110.0299 (15)0.0286 (16)0.0252 (17)−0.0032 (12)0.0037 (12)−0.0016 (13)
C120.0375 (16)0.0338 (18)0.0261 (17)−0.0087 (13)0.0143 (13)−0.0032 (13)
C130.0282 (15)0.0321 (18)0.042 (2)−0.0063 (13)0.0195 (14)−0.0083 (14)
C140.0343 (16)0.0253 (17)0.0368 (19)−0.0026 (12)0.0093 (14)0.0030 (14)
C150.0319 (15)0.0325 (17)0.0249 (17)−0.0028 (13)0.0074 (12)0.0021 (13)
C160.0392 (17)0.0366 (19)0.0297 (18)−0.0024 (14)0.0119 (14)−0.0007 (14)
C170.0323 (15)0.0288 (16)0.0230 (16)0.0051 (12)0.0078 (12)0.0040 (13)
C180.0275 (14)0.0264 (16)0.0219 (16)−0.0023 (12)0.0066 (12)−0.0007 (12)
C190.0217 (14)0.0261 (16)0.0252 (16)−0.0056 (11)0.0063 (12)−0.0053 (12)
C200.0246 (14)0.0247 (16)0.0278 (17)−0.0064 (11)0.0092 (12)−0.0040 (12)
C210.0225 (14)0.0382 (18)0.0264 (17)−0.0013 (12)0.0037 (12)0.0014 (14)
C220.0252 (15)0.048 (2)0.0335 (19)−0.0034 (14)0.0135 (13)−0.0036 (15)
C230.0367 (17)0.042 (2)0.0220 (17)−0.0119 (14)0.0065 (13)−0.0025 (14)
C240.0372 (17)0.0315 (17)0.0264 (18)−0.0010 (13)0.0045 (13)0.0038 (14)
C250.0358 (16)0.0246 (16)0.0304 (18)−0.0012 (12)0.0095 (13)−0.0024 (13)
C260.051 (2)0.0265 (18)0.044 (2)−0.0055 (14)0.0128 (16)−0.0038 (15)
C270.0309 (15)0.0277 (17)0.0378 (19)0.0045 (13)0.0114 (13)0.0111 (14)
C280.0322 (16)0.0238 (16)0.0308 (17)0.0017 (12)0.0104 (13)0.0044 (13)
C290.0188 (13)0.0333 (17)0.0233 (16)0.0011 (11)0.0037 (11)−0.0025 (13)
C300.0241 (14)0.0329 (17)0.0266 (17)−0.0024 (12)0.0096 (12)−0.0024 (13)
C310.0313 (16)0.0394 (19)0.0308 (18)−0.0061 (13)0.0090 (13)−0.0066 (14)
C320.0437 (18)0.039 (2)0.040 (2)−0.0163 (15)0.0159 (16)−0.0134 (16)
C330.0451 (19)0.0347 (19)0.051 (2)−0.0057 (15)0.0221 (17)0.0033 (16)
C340.0353 (17)0.040 (2)0.038 (2)−0.0031 (14)0.0156 (14)0.0073 (15)
C350.0251 (15)0.0378 (18)0.0311 (18)−0.0026 (13)0.0077 (13)−0.0009 (14)
C360.0419 (17)0.0302 (17)0.0327 (19)0.0070 (13)0.0182 (14)0.0055 (14)

Geometric parameters (Å, °)

S1—C81.730 (3)C13—C141.368 (4)
S1—C71.842 (3)C13—H130.9500
S2—C181.736 (3)C14—C151.390 (4)
S2—C171.822 (3)C14—H140.9500
S3—C281.733 (3)C15—H150.9500
S3—C271.833 (3)C16—H16A0.9800
O1—C81.364 (3)C16—H16B0.9800
O1—C91.365 (3)C16—H16C0.9800
O2—C181.364 (3)C17—H17A0.9900
O2—C191.368 (3)C17—H17B0.9900
O3—C281.360 (3)C19—C201.453 (4)
O3—C291.376 (3)C20—C251.389 (4)
N1—C81.292 (4)C20—C211.395 (4)
N1—N21.417 (4)C21—C221.392 (4)
N2—C91.290 (4)C21—H210.9500
N3—C181.291 (4)C22—C231.386 (4)
N3—N41.416 (3)C22—H220.9500
N4—C191.298 (4)C23—C241.384 (4)
N5—C281.291 (4)C23—H230.9500
N5—N61.421 (4)C24—C251.377 (4)
N6—C291.284 (4)C24—H240.9500
C1—C21.399 (4)C25—H250.9500
C1—C61.412 (4)C26—H26A0.9800
C1—C71.509 (4)C26—H26B0.9800
C2—C31.404 (4)C26—H26C0.9800
C2—C161.518 (4)C27—H27A0.9900
C3—C41.403 (4)C27—H27B0.9900
C3—C171.520 (4)C29—C301.457 (4)
C4—C51.398 (4)C30—C351.392 (4)
C4—C261.507 (4)C30—C311.393 (4)
C5—C61.403 (4)C31—C321.385 (5)
C5—C271.512 (4)C31—H310.9500
C6—C361.518 (4)C32—C331.382 (5)
C7—H7A0.9900C32—H320.9500
C7—H7B0.9900C33—C341.390 (5)
C9—C101.455 (4)C33—H330.9500
C10—C151.393 (4)C34—C351.384 (4)
C10—C111.400 (4)C34—H340.9500
C11—C121.371 (4)C35—H350.9500
C11—H110.9500C36—H36A0.9800
C12—C131.409 (4)C36—H36B0.9800
C12—H120.9500C36—H36C0.9800
C8—S1—C7100.65 (14)C3—C17—H17B109.3
C18—S2—C1796.89 (14)S2—C17—H17B109.3
C28—S3—C27101.01 (14)H17A—C17—H17B108.0
C8—O1—C9102.7 (2)N3—C18—O2113.7 (2)
C18—O2—C19102.3 (2)N3—C18—S2130.3 (2)
C28—O3—C29102.6 (2)O2—C18—S2116.0 (2)
C8—N1—N2105.6 (2)N4—C19—O2112.1 (2)
C9—N2—N1106.5 (2)N4—C19—C20129.1 (3)
C18—N3—N4105.1 (2)O2—C19—C20118.7 (2)
C19—N4—N3106.7 (2)C25—C20—C21119.9 (3)
C28—N5—N6104.8 (2)C25—C20—C19120.0 (3)
C29—N6—N5107.5 (2)C21—C20—C19120.1 (3)
C2—C1—C6119.4 (3)C22—C21—C20119.2 (3)
C2—C1—C7120.4 (3)C22—C21—H21120.4
C6—C1—C7120.1 (3)C20—C21—H21120.4
C1—C2—C3119.7 (3)C23—C22—C21120.4 (3)
C1—C2—C16119.9 (3)C23—C22—H22119.8
C3—C2—C16120.4 (3)C21—C22—H22119.8
C4—C3—C2120.8 (3)C24—C23—C22120.0 (3)
C4—C3—C17120.5 (3)C24—C23—H23120.0
C2—C3—C17118.5 (3)C22—C23—H23120.0
C5—C4—C3119.2 (3)C25—C24—C23120.1 (3)
C5—C4—C26120.5 (3)C25—C24—H24119.9
C3—C4—C26120.3 (3)C23—C24—H24119.9
C4—C5—C6120.3 (3)C24—C25—C20120.3 (3)
C4—C5—C27119.9 (3)C24—C25—H25119.8
C6—C5—C27119.8 (3)C20—C25—H25119.8
C5—C6—C1120.2 (3)C4—C26—H26A109.5
C5—C6—C36120.7 (3)C4—C26—H26B109.5
C1—C6—C36119.1 (3)H26A—C26—H26B109.5
C1—C7—S1110.14 (19)C4—C26—H26C109.5
C1—C7—H7A109.6H26A—C26—H26C109.5
S1—C7—H7A109.6H26B—C26—H26C109.5
C1—C7—H7B109.6C5—C27—S3107.24 (19)
S1—C7—H7B109.6C5—C27—H27A110.3
H7A—C7—H7B108.1S3—C27—H27A110.3
N1—C8—O1112.8 (3)C5—C27—H27B110.3
N1—C8—S1130.7 (2)S3—C27—H27B110.3
O1—C8—S1116.5 (2)H27A—C27—H27B108.5
N2—C9—O1112.3 (3)N5—C28—O3113.5 (2)
N2—C9—C10128.4 (3)N5—C28—S3130.4 (2)
O1—C9—C10119.3 (2)O3—C28—S3116.1 (2)
C15—C10—C11119.5 (3)N6—C29—O3111.6 (3)
C15—C10—C9120.7 (3)N6—C29—C30129.8 (3)
C11—C10—C9119.8 (3)O3—C29—C30118.5 (2)
C12—C11—C10120.2 (3)C35—C30—C31119.5 (3)
C12—C11—H11119.9C35—C30—C29121.3 (3)
C10—C11—H11119.9C31—C30—C29119.2 (3)
C11—C12—C13120.1 (3)C32—C31—C30120.0 (3)
C11—C12—H12120.0C32—C31—H31120.0
C13—C12—H12120.0C30—C31—H31120.0
C14—C13—C12119.6 (3)C33—C32—C31120.3 (3)
C14—C13—H13120.2C33—C32—H32119.9
C12—C13—H13120.2C31—C32—H32119.9
C13—C14—C15120.8 (3)C32—C33—C34120.1 (3)
C13—C14—H14119.6C32—C33—H33120.0
C15—C14—H14119.6C34—C33—H33120.0
C14—C15—C10119.7 (3)C35—C34—C33119.8 (3)
C14—C15—H15120.1C35—C34—H34120.1
C10—C15—H15120.1C33—C34—H34120.1
C2—C16—H16A109.5C34—C35—C30120.3 (3)
C2—C16—H16B109.5C34—C35—H35119.9
H16A—C16—H16B109.5C30—C35—H35119.9
C2—C16—H16C109.5C6—C36—H36A109.5
H16A—C16—H16C109.5C6—C36—H36B109.5
H16B—C16—H16C109.5H36A—C36—H36B109.5
C3—C17—S2111.49 (19)C6—C36—H36C109.5
C3—C17—H17A109.3H36A—C36—H36C109.5
S2—C17—H17A109.3H36B—C36—H36C109.5
C8—N1—N2—C90.4 (3)C9—C10—C15—C14179.0 (3)
C18—N3—N4—C190.4 (3)C4—C3—C17—S2−91.9 (3)
C28—N5—N6—C29−0.1 (3)C2—C3—C17—S293.2 (3)
C6—C1—C2—C35.9 (4)C18—S2—C17—C3−172.6 (2)
C7—C1—C2—C3−174.4 (2)N4—N3—C18—O2−0.8 (3)
C6—C1—C2—C16−174.9 (2)N4—N3—C18—S2178.8 (2)
C7—C1—C2—C164.8 (4)C19—O2—C18—N30.8 (3)
C1—C2—C3—C4−7.5 (4)C19—O2—C18—S2−178.82 (18)
C16—C2—C3—C4173.3 (3)C17—S2—C18—N3−5.2 (3)
C1—C2—C3—C17167.3 (2)C17—S2—C18—O2174.3 (2)
C16—C2—C3—C17−11.9 (4)N3—N4—C19—O20.1 (3)
C2—C3—C4—C53.0 (4)N3—N4—C19—C20−179.1 (3)
C17—C3—C4—C5−171.7 (3)C18—O2—C19—N4−0.5 (3)
C2—C3—C4—C26−175.8 (3)C18—O2—C19—C20178.8 (2)
C17—C3—C4—C269.5 (4)N4—C19—C20—C25−177.6 (3)
C3—C4—C5—C63.0 (4)O2—C19—C20—C253.2 (4)
C26—C4—C5—C6−178.2 (3)N4—C19—C20—C211.6 (5)
C3—C4—C5—C27−178.4 (2)O2—C19—C20—C21−177.6 (2)
C26—C4—C5—C270.4 (4)C25—C20—C21—C220.1 (4)
C4—C5—C6—C1−4.5 (4)C19—C20—C21—C22−179.1 (3)
C27—C5—C6—C1176.8 (2)C20—C21—C22—C23−0.5 (4)
C4—C5—C6—C36178.0 (3)C21—C22—C23—C240.1 (5)
C27—C5—C6—C36−0.6 (4)C22—C23—C24—C250.8 (5)
C2—C1—C6—C50.1 (4)C23—C24—C25—C20−1.2 (5)
C7—C1—C6—C5−179.7 (2)C21—C20—C25—C240.8 (4)
C2—C1—C6—C36177.5 (2)C19—C20—C25—C24−180.0 (3)
C7—C1—C6—C36−2.2 (4)C4—C5—C27—S3−98.1 (3)
C2—C1—C7—S1−102.4 (3)C6—C5—C27—S380.5 (3)
C6—C1—C7—S177.3 (3)C28—S3—C27—C5160.8 (2)
C8—S1—C7—C1−125.3 (2)N6—N5—C28—O31.1 (3)
N2—N1—C8—O1−0.7 (3)N6—N5—C28—S3−176.8 (3)
N2—N1—C8—S1178.4 (2)C29—O3—C28—N5−1.5 (3)
C9—O1—C8—N10.8 (3)C29—O3—C28—S3176.7 (2)
C9—O1—C8—S1−178.54 (19)C27—S3—C28—N5−4.7 (3)
C7—S1—C8—N1−17.2 (3)C27—S3—C28—O3177.5 (2)
C7—S1—C8—O1161.9 (2)N5—N6—C29—O3−0.8 (3)
N1—N2—C9—O10.1 (3)N5—N6—C29—C30176.3 (3)
N1—N2—C9—C10180.0 (3)C28—O3—C29—N61.4 (3)
C8—O1—C9—N2−0.5 (3)C28—O3—C29—C30−176.1 (3)
C8—O1—C9—C10179.6 (2)N6—C29—C30—C35157.2 (3)
N2—C9—C10—C15179.8 (3)O3—C29—C30—C35−25.9 (4)
O1—C9—C10—C15−0.3 (4)N6—C29—C30—C31−23.5 (5)
N2—C9—C10—C11−1.8 (5)O3—C29—C30—C31153.4 (3)
O1—C9—C10—C11178.1 (2)C35—C30—C31—C321.0 (5)
C15—C10—C11—C12−0.1 (4)C29—C30—C31—C32−178.3 (3)
C9—C10—C11—C12−178.4 (3)C30—C31—C32—C33−0.2 (5)
C10—C11—C12—C13−0.6 (4)C31—C32—C33—C34−1.0 (5)
C11—C12—C13—C140.7 (4)C32—C33—C34—C351.3 (5)
C12—C13—C14—C15−0.1 (4)C33—C34—C35—C30−0.4 (5)
C13—C14—C15—C10−0.6 (4)C31—C30—C35—C34−0.7 (4)
C11—C10—C15—C140.7 (4)C29—C30—C35—C34178.6 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C31—H31···N5i0.952.553.338 (3)141
C24—H24···N2ii0.952.573.394 (4)146

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2772).

References

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  • Rigaku/MSC (1999). CrystalClear MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, Y. T., Tong, M. L., Fan, H. H., Wang, H. Z. & Chen, X. M. (2005). Dalton Trans. pp. 424–426. [PubMed]
  • Zhang, Z.-H., Li, C.-P., Tian, Y.-L. & Guo, Y.-M. (2007). Acta Cryst. E63, m3044.

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