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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o188.
Published online 2007 December 6. doi:  10.1107/S1600536807063854
PMCID: PMC2915251

4-(4-Chloro­phen­yl)-5-(4-nitro­phen­yl)-3-phenyl-4H-1,2,4-triazole

Abstract

The title compound, C20H13ClN4O2, was synthesized by the condensation of 4-nitro­benzohydrazide and N-(4-chlorophen­yl)­benzimidoyl chloride in N,N-dimethyl­acetamide. The asymmetric unit contains two independent mol­ecules. In one molecule, the triazole ring is oriented at dihedral angles of 23.1 (5), 85.4 (1) and 10.5 (1)° with respect to the phenyl, chlorophenyl and nitrophenyl rings, respectively. In the other molecule, the corresponding dihedral angles are 29.8 (9), 73.4 (7) and 16.4 (3)°.

Related literature

For related literature, see: Kido et al. (1993 [triangle]); Li et al. (2006 [triangle]); Zhu et al. (2000 [triangle], 2001 [triangle]).

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Object name is e-64-0o188-scheme1.jpg

Experimental

Crystal data

  • C20H13ClN4O2
  • M r = 376.79
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o188-efi1.jpg
  • a = 11.4042 (7) Å
  • b = 7.1250 (4) Å
  • c = 43.506 (3) Å
  • β = 96.789 (4)°
  • V = 3510.3 (4) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 113 (2) K
  • 0.20 × 0.18 × 0.10 mm

Data collection

  • Rigaku Saturn diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.953, T max = 0.976
  • 19182 measured reflections
  • 6106 independent reflections
  • 4422 reflections with I > 2σ(I)
  • R int = 0.063

Refinement

  • R[F 2 > 2σ(F 2)] = 0.059
  • wR(F 2) = 0.149
  • S = 1.07
  • 6106 reflections
  • 489 parameters
  • H-atom parameters constrained
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: Crystal­Structure (Rigaku/MSC, 2004 [triangle]); software used to prepare material for publication: CrystalStructure.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063854/sg2206sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063854/sg2206Isup2.hkl

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

supplementary crystallographic information

Comment

In recent years, the 1,2,4-triazole derivatives have received attention (Zhu et al., 2000 and Zhu et al., 2001, Kido et al., 1993 and Li et al., 2006). We report here the crystal structure of 4-(4-chlorophenyl)-3-pheny-5-(4-nitrophenyl)-1,2,4-triazole.

In the molecule of the title compound, (I), (Fig. 1), the asymmetric unit contains two independent molecules and the bond lengths and angles are within normal ranges. In one of the molecules, the triazole ring is oriented with dihedral angles of 9.8 (0), 23.1 (5) and 88.0 (7) ° with respect to the nitrophenyl, phenyl and chlorophenyl rings, respectively. In the other molecule the triazole ring is oriented with dihedral angles of 15.7 (1), 29.8 (7) and 73.7 (4) ° with respect to the nitrophenyl, phenyl and chlorophenyl rings, respectively.

Experimental

4-(4-chlorophenyl)-3-pheny-5-(4-nitrophenyl)-1,2,4-triazole was synthesized by the reaction of 4-nitrobenzohydrazide (2.0 g, 11.0 mmol) and N-(4-clorophenyl)-benzimidoyl chloride (2.75 g, 11.0 mmol) in N,N-dimethyl-acetamide (20 ml). The mixture was stirred and refluxed for 5 h. After cooling, the product crystallized from the orange reaction mixture. It was filtered off, washed with N,N-dimethyl-acetamide and dried in vacuo. The crude sample was purified on a silica-gel column using an cyclohexane-ethyl acetate (1:10 v/v) solvent mixture as eluant. The compound was crystallized by slow evaporation of the ethyl acetate solution in 15 d (yield; 57%, m.p. 507 K).

Refinement

H atoms were positioned geometrically,with C—H = 0.93 for aromatic H, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.2 for aromatic H.

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C20H13ClN4O2Dx = 1.426 Mg m3
Mr = 376.79Melting point: 507 K
Monoclinic, P21/cMo Kα radiation λ = 0.71070 Å
a = 11.4042 (7) ÅCell parameters from 5260 reflections
b = 7.1250 (4) Åθ = 1.8–28.0º
c = 43.506 (3) ŵ = 0.24 mm1
β = 96.789 (4)ºT = 113 (2) K
V = 3510.3 (4) Å3Prism, colorless
Z = 80.20 × 0.18 × 0.10 mm
F000 = 1552

Data collection

Rigaku Saturn diffractometer6106 independent reflections
Radiation source: Rotating anode4422 reflections with I > 2σ(I)
Monochromator: confocalRint = 0.063
Detector resolution: 7.31 pixels mm-1θmax = 25.0º
T = 113(2) Kθmin = 1.8º
ω scansh = −13→13
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)k = −8→8
Tmin = 0.953, Tmax = 0.976l = −51→51
19182 measured reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.059  w = 1/[σ2(Fo2) + (0.0587P)2 + 0.6306P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.149(Δ/σ)max = 0.001
S = 1.07Δρmax = 0.41 e Å3
6106 reflectionsΔρmin = −0.30 e Å3
489 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0049 (6)
Secondary atom site location: difference Fourier map

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
Cl11.38208 (6)0.24773 (10)0.171553 (16)0.0289 (2)
Cl20.10925 (6)0.74945 (11)0.093692 (18)0.0385 (3)
O10.9219 (2)0.1877 (5)−0.01222 (5)0.0773 (9)
O20.7337 (2)0.2379 (4)−0.02133 (5)0.0628 (8)
O30.58746 (19)0.7653 (3)−0.04897 (5)0.0414 (6)
O40.78012 (19)0.7469 (3)−0.04580 (5)0.0396 (6)
N10.85403 (19)0.2199 (3)0.15324 (5)0.0210 (5)
N20.67085 (19)0.2131 (3)0.16657 (5)0.0243 (6)
N30.66417 (19)0.2252 (3)0.13432 (5)0.0223 (5)
N40.8253 (3)0.2192 (4)−0.00327 (6)0.0430 (7)
N50.63553 (18)0.7487 (3)0.11974 (5)0.0199 (5)
N60.81267 (19)0.7365 (3)0.14752 (5)0.0240 (6)
N70.82888 (19)0.7458 (3)0.11606 (5)0.0244 (6)
N80.6869 (2)0.7568 (3)−0.03384 (5)0.0303 (6)
C10.7847 (2)0.2086 (4)0.17762 (6)0.0216 (6)
C20.7737 (2)0.2294 (4)0.12665 (6)0.0208 (6)
C30.9823 (2)0.2244 (4)0.15602 (6)0.0207 (6)
C41.0401 (2)0.3942 (4)0.15194 (6)0.0233 (7)
H40.99600.50410.14600.028*
C51.1634 (2)0.4007 (4)0.15672 (6)0.0227 (6)
H51.20360.51520.15410.027*
C61.2271 (2)0.2373 (4)0.16536 (6)0.0220 (6)
C71.1694 (2)0.0653 (4)0.16860 (6)0.0267 (7)
H71.2137−0.04530.17390.032*
C81.0458 (2)0.0589 (4)0.16395 (6)0.0245 (7)
H81.0054−0.05600.16610.029*
C90.8272 (2)0.1976 (4)0.21123 (6)0.0220 (6)
C100.9332 (2)0.2813 (4)0.22481 (6)0.0242 (7)
H100.98410.34090.21200.029*
C110.9638 (3)0.2771 (4)0.25688 (6)0.0261 (7)
H111.03440.33610.26580.031*
C120.8905 (2)0.1861 (4)0.27591 (6)0.0259 (7)
H120.91170.18240.29770.031*
C130.7862 (2)0.1009 (4)0.26271 (6)0.0263 (7)
H130.73720.03760.27560.032*
C140.7532 (2)0.1079 (4)0.23058 (6)0.0233 (7)
H140.68110.05240.22190.028*
C150.7973 (2)0.2343 (4)0.09377 (6)0.0217 (6)
C160.7004 (3)0.2805 (4)0.07159 (6)0.0277 (7)
H160.62720.31450.07840.033*
C170.7105 (3)0.2770 (4)0.04030 (7)0.0298 (7)
H170.64470.30750.02570.036*
C180.8175 (3)0.2289 (4)0.03045 (6)0.0300 (7)
C190.9163 (3)0.1831 (5)0.05147 (7)0.0347 (8)
H190.98910.15020.04430.042*
C200.9053 (3)0.1869 (4)0.08318 (7)0.0318 (7)
H200.97150.15710.09770.038*
C210.6967 (2)0.7373 (4)0.14949 (6)0.0206 (6)
C220.7228 (2)0.7529 (4)0.09990 (6)0.0209 (6)
C230.5074 (2)0.7492 (4)0.11195 (6)0.0204 (6)
C240.4473 (2)0.9204 (4)0.10807 (6)0.0233 (7)
H240.48961.03550.10980.028*
C250.3244 (2)0.9199 (4)0.10167 (6)0.0249 (7)
H250.28211.03480.09920.030*
C260.2640 (2)0.7481 (4)0.09893 (6)0.0245 (7)
C270.3248 (2)0.5776 (4)0.10190 (6)0.0267 (7)
H270.28270.46250.09930.032*
C280.4478 (2)0.5766 (4)0.10870 (6)0.0231 (7)
H280.49010.46160.11110.028*
C290.6464 (2)0.7224 (4)0.17946 (6)0.0220 (6)
C300.5332 (2)0.7865 (4)0.18415 (6)0.0279 (7)
H300.48350.84140.16750.034*
C310.4937 (3)0.7697 (4)0.21329 (7)0.0292 (7)
H310.41710.81340.21620.035*
C320.5654 (3)0.6895 (4)0.23807 (7)0.0345 (8)
H320.53780.67840.25770.041*
C330.6789 (3)0.6254 (4)0.23369 (7)0.0342 (8)
H330.72830.57050.25040.041*
C340.7190 (2)0.6427 (4)0.20469 (6)0.0275 (7)
H340.79600.60040.20190.033*
C350.7066 (2)0.7586 (4)0.06532 (6)0.0227 (7)
C360.5977 (3)0.7906 (4)0.04670 (7)0.0318 (8)
H360.52830.81290.05620.038*
C370.5918 (3)0.7894 (4)0.01435 (7)0.0323 (8)
H370.51860.80970.00190.039*
C380.6938 (3)0.7585 (4)0.00055 (6)0.0254 (7)
C390.8036 (3)0.7287 (4)0.01803 (7)0.0320 (8)
H390.87280.70930.00830.038*
C400.8080 (3)0.7285 (4)0.05017 (6)0.0292 (7)
H400.88160.70740.06230.035*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0160 (4)0.0375 (5)0.0327 (4)0.0006 (3)0.0007 (3)0.0020 (3)
Cl20.0158 (4)0.0543 (6)0.0437 (5)−0.0011 (3)−0.0030 (3)0.0077 (4)
O10.0364 (16)0.164 (3)0.0327 (14)−0.0007 (17)0.0086 (12)−0.0042 (16)
O20.0404 (15)0.121 (3)0.0253 (12)0.0068 (14)−0.0039 (11)0.0018 (13)
O30.0318 (13)0.0629 (17)0.0273 (11)−0.0014 (11)−0.0063 (10)−0.0002 (11)
O40.0327 (13)0.0587 (17)0.0281 (11)−0.0005 (11)0.0062 (10)−0.0019 (10)
N10.0193 (12)0.0231 (14)0.0203 (11)0.0015 (10)0.0009 (9)−0.0006 (10)
N20.0207 (13)0.0278 (15)0.0231 (12)−0.0007 (10)−0.0022 (10)0.0000 (10)
N30.0175 (13)0.0255 (14)0.0235 (12)−0.0006 (10)0.0005 (10)−0.0015 (10)
N40.0365 (17)0.066 (2)0.0266 (14)−0.0034 (15)0.0036 (13)0.0009 (14)
N50.0145 (12)0.0231 (14)0.0214 (11)0.0012 (9)−0.0007 (9)−0.0016 (10)
N60.0196 (13)0.0274 (15)0.0240 (12)0.0024 (10)−0.0014 (10)−0.0020 (11)
N70.0187 (13)0.0284 (15)0.0248 (12)0.0014 (10)−0.0019 (10)−0.0005 (11)
N80.0286 (15)0.0354 (17)0.0263 (13)−0.0022 (12)0.0011 (12)−0.0014 (12)
C10.0190 (15)0.0207 (16)0.0253 (14)−0.0011 (12)0.0038 (12)0.0020 (12)
C20.0209 (15)0.0167 (16)0.0241 (14)−0.0005 (12)0.0002 (12)−0.0002 (12)
C30.0162 (14)0.0282 (17)0.0173 (13)−0.0002 (12)0.0005 (11)−0.0036 (12)
C40.0217 (15)0.0228 (17)0.0252 (14)0.0012 (12)0.0014 (12)0.0000 (13)
C50.0204 (15)0.0241 (17)0.0243 (14)−0.0030 (12)0.0058 (12)0.0021 (12)
C60.0157 (14)0.0282 (18)0.0216 (14)0.0014 (12)0.0000 (11)−0.0006 (12)
C70.0218 (16)0.0227 (18)0.0354 (16)0.0041 (12)0.0017 (13)0.0038 (13)
C80.0227 (16)0.0232 (17)0.0272 (15)−0.0024 (12)0.0010 (12)0.0021 (13)
C90.0215 (15)0.0220 (17)0.0223 (14)0.0026 (12)0.0015 (11)−0.0020 (12)
C100.0229 (16)0.0272 (18)0.0224 (14)−0.0021 (12)0.0021 (12)−0.0033 (13)
C110.0261 (16)0.0236 (17)0.0278 (15)−0.0003 (13)−0.0008 (12)−0.0032 (13)
C120.0346 (18)0.0220 (17)0.0212 (14)0.0038 (13)0.0031 (13)−0.0015 (12)
C130.0313 (17)0.0202 (17)0.0284 (15)0.0022 (13)0.0074 (13)−0.0006 (13)
C140.0229 (15)0.0220 (17)0.0258 (14)−0.0011 (12)0.0060 (12)−0.0004 (12)
C150.0213 (15)0.0206 (17)0.0226 (14)−0.0013 (12)−0.0001 (12)0.0007 (12)
C160.0224 (16)0.0305 (18)0.0295 (16)0.0048 (13)0.0002 (12)0.0022 (13)
C170.0222 (16)0.039 (2)0.0272 (15)−0.0006 (14)−0.0036 (12)0.0019 (14)
C180.0316 (18)0.034 (2)0.0240 (15)−0.0040 (14)0.0037 (13)0.0006 (14)
C190.0223 (16)0.052 (2)0.0298 (16)0.0032 (15)0.0029 (13)−0.0048 (15)
C200.0216 (16)0.046 (2)0.0271 (15)0.0009 (14)−0.0018 (12)−0.0026 (14)
C210.0170 (15)0.0177 (16)0.0259 (14)−0.0004 (11)−0.0029 (11)−0.0030 (12)
C220.0150 (14)0.0219 (17)0.0255 (14)0.0003 (12)0.0015 (11)−0.0014 (12)
C230.0137 (14)0.0277 (18)0.0196 (13)0.0017 (12)0.0006 (11)0.0005 (12)
C240.0208 (15)0.0222 (17)0.0265 (15)0.0019 (12)0.0013 (12)0.0015 (12)
C250.0205 (16)0.0276 (18)0.0264 (15)0.0055 (13)0.0022 (12)0.0057 (13)
C260.0146 (14)0.038 (2)0.0203 (14)0.0010 (13)0.0007 (11)0.0029 (13)
C270.0249 (16)0.0310 (19)0.0241 (15)−0.0063 (13)0.0020 (12)−0.0025 (13)
C280.0213 (16)0.0253 (17)0.0233 (14)0.0017 (12)0.0054 (12)−0.0038 (12)
C290.0229 (16)0.0168 (16)0.0256 (14)−0.0002 (12)−0.0004 (12)−0.0042 (12)
C300.0271 (17)0.0308 (18)0.0251 (15)−0.0004 (13)0.0001 (12)−0.0026 (13)
C310.0253 (16)0.0288 (18)0.0336 (16)−0.0045 (13)0.0044 (13)−0.0042 (14)
C320.046 (2)0.0313 (19)0.0279 (16)−0.0069 (15)0.0093 (14)0.0019 (14)
C330.047 (2)0.0252 (19)0.0285 (16)0.0007 (15)−0.0031 (15)0.0046 (14)
C340.0271 (16)0.0233 (17)0.0310 (16)0.0023 (13)−0.0015 (13)0.0001 (13)
C350.0189 (15)0.0212 (17)0.0273 (15)0.0000 (12)−0.0007 (12)0.0001 (12)
C360.0238 (17)0.042 (2)0.0303 (16)0.0052 (14)0.0042 (13)−0.0020 (14)
C370.0214 (16)0.045 (2)0.0287 (16)0.0048 (14)−0.0044 (13)−0.0036 (14)
C380.0311 (17)0.0252 (18)0.0192 (14)−0.0040 (13)−0.0003 (12)0.0009 (12)
C390.0212 (16)0.045 (2)0.0299 (16)−0.0010 (14)0.0027 (13)−0.0002 (15)
C400.0198 (16)0.039 (2)0.0276 (16)−0.0023 (13)−0.0016 (12)−0.0014 (14)

Geometric parameters (Å, °)

Cl1—C61.757 (3)C15—C201.406 (4)
Cl2—C261.752 (3)C15—C161.417 (4)
O1—N41.231 (3)C16—C171.380 (4)
O2—N41.238 (3)C16—H160.9500
O3—N81.244 (3)C17—C181.383 (4)
O4—N81.240 (3)C17—H170.9500
N1—C21.390 (3)C18—C191.403 (4)
N1—C11.398 (3)C19—C201.400 (4)
N1—C31.454 (3)C19—H190.9500
N2—C11.330 (3)C20—H200.9500
N2—N31.399 (3)C21—C291.490 (4)
N3—C21.330 (3)C22—C351.494 (4)
N4—C181.482 (4)C23—C241.400 (4)
N5—C221.392 (3)C23—C281.404 (4)
N5—C211.398 (3)C24—C251.396 (3)
N5—C231.460 (3)C24—H240.9500
N6—C211.335 (3)C25—C261.403 (4)
N6—N71.404 (3)C25—H250.9500
N7—C221.327 (3)C26—C271.397 (4)
N8—C381.489 (3)C27—C281.399 (4)
C1—C91.487 (4)C27—H270.9500
C2—C151.487 (4)C28—H280.9500
C3—C41.399 (4)C29—C301.406 (4)
C3—C81.405 (4)C29—C341.413 (4)
C4—C51.397 (3)C30—C311.400 (4)
C4—H40.9500C30—H300.9500
C5—C61.400 (4)C31—C321.396 (4)
C5—H50.9500C31—H310.9500
C6—C71.406 (4)C32—C331.407 (4)
C7—C81.401 (4)C32—H320.9500
C7—H70.9500C33—C341.397 (4)
C8—H80.9500C33—H330.9500
C9—C101.413 (4)C34—H340.9500
C9—C141.414 (4)C35—C401.413 (4)
C10—C111.398 (4)C35—C361.419 (4)
C10—H100.9500C36—C371.401 (4)
C11—C121.403 (4)C36—H360.9500
C11—H110.9500C37—C381.388 (4)
C12—C131.397 (4)C37—H370.9500
C12—H120.9500C38—C391.401 (4)
C13—C141.405 (4)C39—C401.393 (4)
C13—H130.9500C39—H390.9500
C14—H140.9500C40—H400.9500
C2—N1—C1104.9 (2)C17—C18—N4118.5 (3)
C2—N1—C3128.8 (2)C19—C18—N4119.8 (3)
C1—N1—C3126.3 (2)C20—C19—C18118.6 (3)
C1—N2—N3107.4 (2)C20—C19—H19120.7
C2—N3—N2108.1 (2)C18—C19—H19120.7
O1—N4—O2122.6 (3)C19—C20—C15120.8 (3)
O1—N4—C18118.9 (3)C19—C20—H20119.6
O2—N4—C18118.6 (3)C15—C20—H20119.6
C22—N5—C21105.1 (2)N6—C21—N5109.3 (2)
C22—N5—C23128.7 (2)N6—C21—C29122.9 (2)
C21—N5—C23126.2 (2)N5—C21—C29127.8 (2)
C21—N6—N7107.9 (2)N7—C22—N5110.2 (2)
C22—N7—N6107.5 (2)N7—C22—C35122.0 (2)
O4—N8—O3123.6 (2)N5—C22—C35127.8 (2)
O4—N8—C38118.4 (2)C24—C23—C28121.8 (2)
O3—N8—C38118.0 (2)C24—C23—N5119.5 (2)
N2—C1—N1109.9 (2)C28—C23—N5118.7 (2)
N2—C1—C9123.2 (2)C25—C24—C23119.2 (3)
N1—C1—C9126.9 (2)C25—C24—H24120.4
N3—C2—N1109.7 (2)C23—C24—H24120.4
N3—C2—C15121.6 (2)C24—C25—C26119.4 (3)
N1—C2—C15128.7 (2)C24—C25—H25120.3
C4—C3—C8121.3 (2)C26—C25—H25120.3
C4—C3—N1119.5 (2)C27—C26—C25121.2 (2)
C8—C3—N1119.1 (2)C27—C26—Cl2119.9 (2)
C5—C4—C3119.4 (2)C25—C26—Cl2118.9 (2)
C5—C4—H4120.3C26—C27—C28119.9 (3)
C3—C4—H4120.3C26—C27—H27120.1
C4—C5—C6119.6 (3)C28—C27—H27120.1
C4—C5—H5120.2C27—C28—C23118.6 (3)
C6—C5—H5120.2C27—C28—H28120.7
C5—C6—C7121.1 (2)C23—C28—H28120.7
C5—C6—Cl1119.2 (2)C30—C29—C34118.8 (3)
C7—C6—Cl1119.7 (2)C30—C29—C21124.0 (2)
C8—C7—C6119.3 (3)C34—C29—C21117.2 (2)
C8—C7—H7120.4C31—C30—C29120.2 (3)
C6—C7—H7120.4C31—C30—H30119.9
C7—C8—C3119.3 (3)C29—C30—H30119.9
C7—C8—H8120.4C32—C31—C30120.8 (3)
C3—C8—H8120.4C32—C31—H31119.6
C10—C9—C14118.9 (2)C30—C31—H31119.6
C10—C9—C1123.6 (2)C31—C32—C33119.5 (3)
C14—C9—C1117.4 (2)C31—C32—H32120.2
C11—C10—C9120.6 (3)C33—C32—H32120.2
C11—C10—H10119.7C34—C33—C32119.9 (3)
C9—C10—H10119.7C34—C33—H33120.1
C10—C11—C12120.2 (3)C32—C33—H33120.1
C10—C11—H11119.9C33—C34—C29120.9 (3)
C12—C11—H11119.9C33—C34—H34119.6
C13—C12—C11119.7 (2)C29—C34—H34119.6
C13—C12—H12120.1C40—C35—C36117.8 (3)
C11—C12—H12120.1C40—C35—C22117.1 (2)
C12—C13—C14120.6 (3)C36—C35—C22125.1 (3)
C12—C13—H13119.7C37—C36—C35120.5 (3)
C14—C13—H13119.7C37—C36—H36119.7
C13—C14—C9120.0 (3)C35—C36—H36119.7
C13—C14—H14120.0C38—C37—C36119.5 (3)
C9—C14—H14120.0C38—C37—H37120.3
C20—C15—C16118.4 (3)C36—C37—H37120.3
C20—C15—C2125.1 (2)C37—C38—C39122.0 (3)
C16—C15—C2116.4 (2)C37—C38—N8119.2 (2)
C17—C16—C15121.2 (3)C39—C38—N8118.8 (3)
C17—C16—H16119.4C40—C39—C38117.9 (3)
C15—C16—H16119.4C40—C39—H39121.0
C16—C17—C18119.3 (3)C38—C39—H39121.0
C16—C17—H17120.3C39—C40—C35122.3 (3)
C18—C17—H17120.3C39—C40—H40118.9
C17—C18—C19121.7 (3)C35—C40—H40118.9
C1—N2—N3—C2−0.5 (3)C2—C15—C20—C19175.4 (3)
C21—N6—N7—C220.3 (3)N7—N6—C21—N5−0.5 (3)
N3—N2—C1—N10.7 (3)N7—N6—C21—C29177.9 (2)
N3—N2—C1—C9179.4 (2)C22—N5—C21—N60.5 (3)
C2—N1—C1—N2−0.7 (3)C23—N5—C21—N6178.6 (2)
C3—N1—C1—N2178.2 (2)C22—N5—C21—C29−177.8 (2)
C2—N1—C1—C9−179.3 (3)C23—N5—C21—C290.3 (4)
C3—N1—C1—C9−0.4 (4)N6—N7—C22—N50.1 (3)
N2—N3—C2—N10.1 (3)N6—N7—C22—C35−178.3 (2)
N2—N3—C2—C15177.5 (2)C21—N5—C22—N7−0.3 (3)
C1—N1—C2—N30.3 (3)C23—N5—C22—N7−178.4 (2)
C3—N1—C2—N3−178.5 (2)C21—N5—C22—C35177.9 (2)
C1—N1—C2—C15−176.8 (3)C23—N5—C22—C35−0.1 (4)
C3—N1—C2—C154.3 (4)C22—N5—C23—C24−87.9 (3)
C2—N1—C3—C474.4 (3)C21—N5—C23—C2494.5 (3)
C1—N1—C3—C4−104.2 (3)C22—N5—C23—C2892.4 (3)
C2—N1—C3—C8−108.0 (3)C21—N5—C23—C28−85.2 (3)
C1—N1—C3—C873.4 (3)C28—C23—C24—C251.9 (4)
C8—C3—C4—C5−1.9 (4)N5—C23—C24—C25−177.8 (2)
N1—C3—C4—C5175.6 (2)C23—C24—C25—C26−0.7 (4)
C3—C4—C5—C60.3 (4)C24—C25—C26—C27−1.3 (4)
C4—C5—C6—C71.6 (4)C24—C25—C26—Cl2175.4 (2)
C4—C5—C6—Cl1−179.57 (19)C25—C26—C27—C282.1 (4)
C5—C6—C7—C8−1.8 (4)Cl2—C26—C27—C28−174.6 (2)
Cl1—C6—C7—C8179.3 (2)C26—C27—C28—C23−0.9 (4)
C6—C7—C8—C30.3 (4)C24—C23—C28—C27−1.1 (4)
C4—C3—C8—C71.6 (4)N5—C23—C28—C27178.6 (2)
N1—C3—C8—C7−175.9 (2)N6—C21—C29—C30156.8 (3)
N2—C1—C9—C10−147.5 (3)N5—C21—C29—C30−25.1 (4)
N1—C1—C9—C1030.9 (4)N6—C21—C29—C34−21.6 (4)
N2—C1—C9—C1428.5 (4)N5—C21—C29—C34156.5 (3)
N1—C1—C9—C14−153.0 (3)C34—C29—C30—C31−0.5 (4)
C14—C9—C10—C11−0.6 (4)C21—C29—C30—C31−178.9 (2)
C1—C9—C10—C11175.4 (2)C29—C30—C31—C320.0 (4)
C9—C10—C11—C121.3 (4)C30—C31—C32—C330.2 (4)
C10—C11—C12—C13−0.6 (4)C31—C32—C33—C340.1 (5)
C11—C12—C13—C14−0.9 (4)C32—C33—C34—C29−0.6 (4)
C12—C13—C14—C91.6 (4)C30—C29—C34—C330.8 (4)
C10—C9—C14—C13−0.9 (4)C21—C29—C34—C33179.3 (3)
C1—C9—C14—C13−177.1 (2)N7—C22—C35—C409.0 (4)
N3—C2—C15—C20−161.3 (3)N5—C22—C35—C40−169.0 (2)
N1—C2—C15—C2015.6 (4)N7—C22—C35—C36−171.4 (3)
N3—C2—C15—C1615.0 (4)N5—C22—C35—C3610.5 (4)
N1—C2—C15—C16−168.1 (3)C40—C35—C36—C370.8 (4)
C20—C15—C16—C170.8 (4)C22—C35—C36—C37−178.7 (3)
C2—C15—C16—C17−175.7 (3)C35—C36—C37—C38−0.6 (5)
C15—C16—C17—C18−0.5 (4)C36—C37—C38—C39−0.2 (4)
C16—C17—C18—C190.0 (5)C36—C37—C38—N8179.8 (3)
C16—C17—C18—N4177.8 (3)O4—N8—C38—C37173.2 (2)
O1—N4—C18—C17175.6 (3)O3—N8—C38—C37−6.8 (4)
O2—N4—C18—C17−6.4 (4)O4—N8—C38—C39−6.8 (4)
O1—N4—C18—C19−6.6 (5)O3—N8—C38—C39173.2 (2)
O2—N4—C18—C19171.4 (3)C37—C38—C39—C400.8 (4)
C17—C18—C19—C200.0 (5)N8—C38—C39—C40−179.2 (2)
N4—C18—C19—C20−177.7 (3)C38—C39—C40—C35−0.6 (4)
C18—C19—C20—C150.4 (5)C36—C35—C40—C39−0.2 (4)
C16—C15—C20—C19−0.8 (4)C22—C35—C40—C39179.3 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2206).

References

  • Kido, J., Hongawa, K., Okuyama, K. & Nagai, K. (1993). Appl. Phys. Lett.63, 2627–2629.
  • Li, Z. H., Wong, M. S., Fukutani, H. & Tao, Y. (2006). Org. Lett.8, 4271–4274. [PubMed]
  • Rigaku (2005). CrystalClear Version 1.3.6. Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2004). CrystalStructure Version 3.7.0. Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Zhu, D., Xu, Y., Mei, Y. H., Shi, Y. J., Tu, C. & You, X. Z. (2001). J. Mol. Struct.559, 119–125.
  • Zhu, D., Zhu, X. L., Xu, L., Shao, S. C., Raj, S. S. S., Fun, H. K. & You, X. Z. (2000). J. Chem. Crystallogr.30, 429–432.

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