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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o188
https://doi.org/10.1107/S1600536807063854

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

Jing Hu,a* Hongguang Song,a Guofeng Chena,b and Guochun Maa

aDepartment of Chemistry, Tianjin University, Tianjin 300072, People's Republic of China, and bDepartment of Chemistry, Hebei University, Baoding 071002, People's Republic of China
*Correspondence e-mail: hujing8012@yahoo.com.cn

(Received 13 November 2007; accepted 27 November 2007; online 6 December 2007)

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[Kido, J., Hongawa, K., Okuyama, K. & Nagai, K. (1993). Appl. Phys. Lett. 63, 2627-2629.]); Li et al. (2006[Li, Z. H., Wong, M. S., Fukutani, H. & Tao, Y. (2006). Org. Lett. 8, 4271-4274.]); Zhu et al. (2000[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.], 2001[Zhu, D., Xu, Y., Mei, Y. H., Shi, Y. J., Tu, C. & You, X. Z. (2001). J. Mol. Struct. 559, 119-125.]).

[Scheme 1]

Experimental

Crystal data

  • C20H13ClN4O2

  • Mr = 376.79

  • Monoclinic, P 21 /c

  • 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[Rigaku (2005). CrystalClear. Version 1.3.6. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.953, Tmax = 0.976

  • 19182 measured reflections

  • 6106 independent reflections

  • 4422 reflections with I > 2σ(I)

  • Rint = 0.063
Refinement

  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 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[Rigaku (2005). CrystalClear. Version 1.3.6. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: Crystal­Structure (Rigaku/MSC, 2004[Rigaku/MSC (2004). CrystalStructure. Version 3.7.0. Rigaku/MSC, The Woodlands, Texas, USA.]); software used to prepare material for publication: CrystalStructure.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807063854/sg2206Isup2.hkl

checkCIF report


Comment top

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.

Related literature top

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

Experimental top

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 top

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.

Structure description top

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.

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

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
4-(4-Chlorophenyl)-5-(4-nitrophenyl)-3-phenyl-4H-1,2,4-triazole top
Crystal data top
C20H13ClN4O2Dx = 1.426 Mg m−3
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 = 1.8–28.0°
c = 43.506 (3) ŵ = 0.24 mm−1
β = 96.789 (4)°T = 113 K
V = 3510.3 (4) Å3Prism, colorless
Z = 80.20 × 0.18 × 0.10 mm
F(000) = 1552
Data collection top
Rigaku Saturn
diffractometer		6106 independent reflections
Radiation source: Rotating anode4422 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.063
Detector resolution: 7.31 pixels mm-1θmax = 25.0°, θmin = 1.8°
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 top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.149 w = 1/[σ2(Fo2) + (0.0587P)2 + 0.6306P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
6106 reflectionsΔρmax = 0.41 e Å−3
489 parametersΔρmin = −0.30 e Å−3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0049 (6)
Crystal data top
C20H13ClN4O2V = 3510.3 (4) Å3
Mr = 376.79Z = 8
Monoclinic, P21/cMo Kα radiation
a = 11.4042 (7) ŵ = 0.24 mm−1
b = 7.1250 (4) ÅT = 113 K
c = 43.506 (3) Å0.20 × 0.18 × 0.10 mm
β = 96.789 (4)°
Data collection top
Rigaku Saturn
diffractometer		6106 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		4422 reflections with I > 2σ(I)
Tmin = 0.953, Tmax = 0.976Rint = 0.063
19182 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.149H-atom parameters constrained
S = 1.07Δρmax = 0.41 e Å−3
6106 reflectionsΔρmin = −0.30 e Å−3
489 parameters
Special details top

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
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) top
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, º) top
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)

Experimental details

Crystal data
Chemical formulaC20H13ClN4O2
Mr376.79
Crystal system, space groupMonoclinic, P21/c
Temperature (K)113
a, b, c (Å)11.4042 (7), 7.1250 (4), 43.506 (3)
β (°) 96.789 (4)
V (Å3)3510.3 (4)
Z8
Radiation typeMo Kα
µ (mm−1)0.24
Crystal size (mm)0.20 × 0.18 × 0.10
Data collection
DiffractometerRigaku Saturn
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.953, 0.976
No. of measured, independent and
observed [I > 2σ(I)] reflections		19182, 6106, 4422
Rint0.063
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.149, 1.07
No. of reflections6106
No. of parameters489
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.41, −0.30

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), CrystalStructure (Rigaku/MSC, 2004).

 

References

First citationKido, J., Hongawa, K., Okuyama, K. & Nagai, K. (1993). Appl. Phys. Lett. 63, 2627–2629.  CrossRef CAS Web of Science Google Scholar
 First citationLi, Z. H., Wong, M. S., Fukutani, H. & Tao, Y. (2006). Org. Lett. 8, 4271–4274.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationRigaku (2005). CrystalClear. Version 1.3.6. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationRigaku/MSC (2004). CrystalStructure. Version 3.7.0. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar
 First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
 First citationZhu, D., Xu, Y., Mei, Y. H., Shi, Y. J., Tu, C. & You, X. Z. (2001). J. Mol. Struct. 559, 119–125.  Web of Science CSD CrossRef CAS Google Scholar
 First citationZhu, 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.  Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o188
https://doi.org/10.1107/S1600536807063854
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