1-(2-Chloro­benzyl­idene)-2-(2,4-dinitro­phen­yl)hydrazine

Shi, Z.-Q.; Ji, N.-N.; Li, X.-Y.

doi:10.1107/S1600536808033357

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2135

doi:10.1107/S1600536808033357

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1-(2-Chlorobenzylidene)-2-(2,4-dinitrophenyl)hydrazine

Zhi-Qiang Shi,^a ^* Ning-Ning Ji ^b and Xiao-Yan Li ^c

^aDepartment of Materials Science and Chemical Engineering, Taishan University, 271021 Taian, Shandong, People's Republic of China, ^bDepartment of Chemistry, Taishan University, 271021 Taian, Shandong, People's Republic of China, and ^cNo. 1 Middle School of Lanshan, 276808 Rizhao, Shandong, People's Republic of China
^*Correspondence e-mail: kobeecho@163.com

(Received 12 September 2008; accepted 14 October 2008; online 18 October 2008)

In the title compound, C₁₃H₉ClN₄O₄, there are two crystallographically independent molecules in the asymmetric unit, which have very similar conformations. The C=N—N angles in each independent molecule are 115.0 (2) and 116.6 (2)°, which are significantly smaller than the ideal value of 120° expected for sp²-hybridized N atoms. This is probably a consequence of repulsion between the nitrogen lone pairs and the adjacent N—N bonds. Two bifurcated intramolecular N—H⋯O hydrogen bonds help to establish the molecular conformation and consolidate the crystal packing.

Related literature

For general background, see: Garnovskii et al. (1993 ); Anderson et al. (1997 ); Musie et al. (2001 ); Paul et al. (2002 ); Shi et al. (2007 ); For related structures, see: Baughman et al. (2004 ); Zare et al. (2005 ); El-Seify & El-Dossoki (2006 ); Kim & Yoon (1998 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₃H₉ClN₄O₄
M_r = 320.69
Triclinic, $[P \overline 1]$
a = 7.2286 (7) Å
b = 7.6596 (8) Å
c = 25.145 (2) Å
α = 95.691 (2)°
β = 93.030 (2)°
γ = 99.728 (3)°
V = 1362.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 295 (2) K
0.15 × 0.12 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.956, T_max = 0.976
7216 measured reflections
4776 independent reflections
3273 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.125
S = 1.07
4776 reflections
397 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6⋯O6	0.86	2.02	2.631 (3)	127
N2—H2⋯O1	0.86	2.00	2.622 (3)	129

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033357/fj2153sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033357/fj2153Isup2.hkl

checkCIF report

Comment top

In recent years, a number of Schiff-bases have been investigated in terms of their coordination chemistry (Garnovskii et al., 1993; Musie et al., 2001; Paul et al., 2002; Shi et al., 2007;) and biological systems (Anderson et al., 1997). Especial the 2,4-dinitrophenylhydrazones exhibit good nonlinear optical (NLO) and crystalline properties (Baughman et al., 2004). As a result of their significant molecular nonlinearities and remarkable ability to crystallize in non-centrosymmetric crystal systems (Zare et al., 2005; El-Seify & El-Dossoki, 2006; Kim & Yoon, 1998), many X-ray structural studies of 2,4-dinitrophenylhydrazone have been reported. In order to search for new 2,4-dinitrophenylhydrazones, the title compound, (I), was synthesized and its crystal structure determined. In (I) (Fig. 1), the bond lengths and angles are in good agreement with the expected values (Allen et al., 1987). In the crystal structure (Fig. 2), the molecules are stabilized by intramolecular N—H···O hydrogen bonds.

Related literature top

For general background, see: Garnovskii et al. (1993); Anderson et al. (1997); Musie et al. (2001); Paul et al. (2002); Shi et al. (2007); For related structures, see: Baughman et al. (2004); Zare et al. (2005); El-Seify & El-Dossoki (2006); Kim & Yoon (1998). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was synthesized by the reaction of (2,4-dinitro-phenyl)-hydrazine(1 mmol, 198.1 mg) with 2-Chloro-benzaldehyde (1 mmol, 140.6 mg) in ethanol (20 ml) under reflux conditions (343 K) for 3 h. The solvent was removed and the solid product recrystallized from tetrahydrofuran, and then dried in vacuo to give pure title compound in 89% yield. After five days yellow crystals suitable for X-ray diffraction study were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The molecules are stabilized by intramolecular N—H···O hydrogen bonds. The dashed lines indicate hydrogen bonds.

1-(2-Chlorobenzylidene)-2-(2,4-dinitrophenyl)hydrazine top

Crystal data top

C₁₃H₉ClN₄O₄	Z = 4
M_r = 320.69	F(000) = 656
Triclinic, P1	D_x = 1.564 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2286 (7) Å	Cell parameters from 1793 reflections
b = 7.6596 (8) Å	θ = 2.7–24.9°
c = 25.145 (2) Å	µ = 0.31 mm⁻¹
α = 95.691 (2)°	T = 295 K
β = 93.030 (2)°	Block, yellow
γ = 99.728 (3)°	0.15 × 0.12 × 0.08 mm
V = 1362.0 (2) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	4776 independent reflections
Radiation source: fine-focus sealed tube	3273 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
T_min = 0.956, T_max = 0.976	k = −9→5
7216 measured reflections	l = −28→29

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0511P)² + 0.2987P] where P = (F_o² + 2F_c²)/3
4776 reflections	(Δ/σ)_max = 0.001
397 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₃H₉ClN₄O₄	γ = 99.728 (3)°
M_r = 320.69	V = 1362.0 (2) Å³
Triclinic, P1	Z = 4
a = 7.2286 (7) Å	Mo Kα radiation
b = 7.6596 (8) Å	µ = 0.31 mm⁻¹
c = 25.145 (2) Å	T = 295 K
α = 95.691 (2)°	0.15 × 0.12 × 0.08 mm
β = 93.030 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4776 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3273 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.976	R_int = 0.021
7216 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.07	Δρ_max = 0.42 e Å⁻³
4776 reflections	Δρ_min = −0.36 e Å⁻³
397 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

	x	y	z	U_iso*/U_eq
Cl1	0.32732 (10)	0.39535 (11)	0.21587 (3)	0.0647 (2)
Cl2	0.43812 (11)	0.46461 (12)	0.65151 (3)	0.0739 (3)
O1	1.1413 (3)	0.8066 (3)	0.24502 (8)	0.0769 (6)
O2	1.4364 (3)	0.8957 (4)	0.23973 (8)	0.0901 (8)
O3	1.6810 (3)	1.1413 (4)	0.08840 (11)	0.1047 (9)
O4	1.4958 (3)	1.1774 (3)	0.02231 (9)	0.0754 (6)
O5	−0.0518 (4)	−0.1695 (3)	0.37193 (10)	0.0957 (8)
O6	0.0550 (3)	−0.0357 (3)	0.44708 (4)	0.0817 (7)
O7	−0.1612 (4)	0.1254 (4)	0.22106 (9)	0.0899 (8)
O8	−0.1463 (3)	0.4102 (3)	0.23032 (8)	0.0804 (7)
N1	0.7500 (3)	0.6855 (3)	0.12714 (8)	0.0490 (5)
N2	0.9138 (3)	0.7485 (3)	0.15793 (8)	0.0506 (6)
H2	0.9218	0.7309	0.1912	0.061*
N3	1.2749 (4)	0.8647 (3)	0.21971 (9)	0.0586 (6)
N4	1.5265 (4)	1.1204 (3)	0.06490 (11)	0.0626 (7)
N5	0.2250 (3)	0.4769 (3)	0.48803 (9)	0.0544 (6)
N6	0.1464 (3)	0.3138 (3)	0.46212 (8)	0.0555 (6)
H6	0.1359	0.2206	0.4790	0.067*
N7	0.0038 (3)	−0.0334 (3)	0.40054 (10)	0.0584 (6)
N8	−0.1249 (3)	0.2712 (4)	0.24773 (9)	0.0613 (6)
C1	0.2909 (3)	0.4329 (3)	0.14910 (10)	0.0440 (6)
C2	0.4356 (3)	0.5294 (3)	0.12368 (10)	0.0428 (6)
C3	0.3991 (4)	0.5523 (4)	0.07027 (10)	0.0508 (7)
H3	0.4928	0.6154	0.0522	0.061*
C4	0.2273 (4)	0.4835 (4)	0.04363 (11)	0.0565 (7)
H4	0.2058	0.5001	0.0078	0.068*
C5	0.0867 (4)	0.3899 (4)	0.06992 (11)	0.0558 (7)
H5	−0.0295	0.3438	0.0518	0.067*
C6	0.1179 (4)	0.3646 (3)	0.12285 (11)	0.0506 (7)
H6A	0.0232	0.3020	0.1407	0.061*
C7	0.6178 (3)	0.6038 (3)	0.15160 (10)	0.0470 (6)
H7	0.6378	0.5915	0.1878	0.056*
C8	1.0634 (3)	0.8386 (3)	0.13611 (10)	0.0436 (6)
C9	1.2406 (3)	0.8962 (3)	0.16462 (10)	0.0450 (6)
C10	1.3931 (3)	0.9855 (3)	0.14090 (10)	0.0466 (6)
H10	1.5096	1.0204	0.1599	0.056*
C11	1.3680 (4)	1.0207 (3)	0.08927 (10)	0.0479 (6)
C12	1.1976 (4)	0.9667 (4)	0.05948 (11)	0.0522 (7)
H12	1.1849	0.9913	0.0241	0.063*
C13	1.0483 (4)	0.8770 (3)	0.08255 (10)	0.0501 (7)
H13	0.9341	0.8404	0.0625	0.060*
C14	0.4405 (4)	0.6574 (4)	0.62064 (11)	0.0555 (7)
C15	0.3642 (4)	0.6497 (4)	0.56796 (10)	0.0517 (7)
C16	0.3711 (4)	0.8103 (4)	0.54624 (12)	0.0626 (8)
H16	0.3214	0.8099	0.5113	0.075*
C17	0.4496 (4)	0.9698 (5)	0.57508 (13)	0.0700 (9)
H17	0.4537	1.0755	0.5595	0.084*
C18	0.5230 (4)	0.9733 (5)	0.62741 (13)	0.0713 (9)
H18	0.5753	1.0813	0.6471	0.086*
C19	0.5181 (4)	0.8170 (5)	0.65008 (12)	0.0664 (8)
H19	0.5669	0.8187	0.6851	0.080*
C20	0.2786 (4)	0.4815 (4)	0.53736 (10)	0.0548 (7)
H20	0.2629	0.3771	0.5539	0.066*
C21	0.0852 (3)	0.2998 (4)	0.40979 (10)	0.0451 (6)
C22	0.0134 (3)	0.1353 (3)	0.37897 (10)	0.0461 (6)
C23	−0.0515 (3)	0.1268 (4)	0.32600 (10)	0.0482 (6)
H23	−0.0975	0.0172	0.3064	0.058*
C24	−0.0474 (3)	0.2805 (4)	0.30277 (9)	0.0462 (6)
C25	0.0247 (4)	0.4448 (4)	0.33107 (10)	0.0512 (7)
H25	0.0282	0.5484	0.3145	0.061*
C26	0.0902 (4)	0.4542 (4)	0.38328 (10)	0.0513 (7)
H26	0.1394	0.5649	0.4018	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0580 (4)	0.0837 (5)	0.0489 (4)	−0.0052 (4)	0.0051 (3)	0.0196 (4)
Cl2	0.0731 (5)	0.0892 (6)	0.0596 (5)	0.0129 (4)	−0.0076 (4)	0.0178 (4)
O1	0.0683 (14)	0.1072 (18)	0.0515 (12)	−0.0034 (13)	0.0101 (10)	0.0190 (12)
O2	0.0658 (15)	0.131 (2)	0.0598 (13)	−0.0178 (14)	−0.0154 (11)	0.0137 (13)
O3	0.0540 (14)	0.142 (2)	0.1053 (19)	−0.0302 (15)	0.0087 (14)	0.0299 (17)
O4	0.0938 (17)	0.0597 (13)	0.0773 (15)	0.0076 (12)	0.0342 (12)	0.0249 (12)
O5	0.158 (3)	0.0482 (13)	0.0751 (16)	0.0065 (15)	−0.0070 (15)	0.0038 (12)
O6	0.123 (2)	0.0665 (14)	0.0573 (13)	0.0157 (13)	−0.0011 (13)	0.0240 (11)
O7	0.110 (2)	0.0898 (18)	0.0566 (13)	−0.0106 (15)	−0.0197 (13)	0.0052 (13)
O8	0.0857 (16)	0.1023 (18)	0.0622 (13)	0.0302 (14)	−0.0007 (11)	0.0327 (13)
N1	0.0405 (12)	0.0503 (13)	0.0541 (13)	0.0000 (10)	0.0056 (10)	0.0075 (11)
N2	0.0407 (12)	0.0596 (14)	0.0483 (12)	−0.0026 (11)	0.0055 (10)	0.0087 (11)
N3	0.0588 (15)	0.0641 (16)	0.0468 (13)	−0.0031 (13)	0.0014 (12)	0.0015 (11)
N4	0.0632 (17)	0.0517 (15)	0.0701 (17)	−0.0032 (13)	0.0235 (14)	0.0057 (13)
N5	0.0539 (14)	0.0647 (16)	0.0447 (13)	0.0106 (12)	0.0054 (11)	0.0056 (12)
N6	0.0634 (15)	0.0572 (15)	0.0458 (13)	0.0082 (12)	0.0013 (11)	0.0114 (11)
N7	0.0695 (16)	0.0589 (16)	0.0513 (15)	0.0147 (13)	0.0099 (12)	0.0185 (13)
N8	0.0507 (14)	0.086 (2)	0.0468 (14)	0.0045 (14)	0.0041 (11)	0.0180 (15)
C1	0.0436 (14)	0.0430 (14)	0.0459 (14)	0.0060 (12)	0.0066 (11)	0.0081 (12)
C2	0.0395 (14)	0.0403 (14)	0.0508 (15)	0.0089 (11)	0.0069 (11)	0.0109 (12)
C3	0.0467 (15)	0.0534 (16)	0.0559 (16)	0.0097 (13)	0.0110 (13)	0.0187 (13)
C4	0.0537 (17)	0.0669 (19)	0.0502 (16)	0.0106 (15)	−0.0001 (13)	0.0155 (14)
C5	0.0441 (15)	0.0583 (18)	0.0625 (18)	0.0037 (13)	−0.0058 (13)	0.0088 (14)
C6	0.0418 (15)	0.0514 (16)	0.0577 (17)	0.0015 (13)	0.0051 (12)	0.0120 (13)
C7	0.0423 (14)	0.0480 (16)	0.0512 (15)	0.0060 (12)	0.0058 (12)	0.0093 (13)
C8	0.0425 (14)	0.0393 (14)	0.0478 (15)	0.0030 (12)	0.0095 (11)	0.0026 (11)
C9	0.0478 (15)	0.0415 (14)	0.0425 (14)	0.0007 (12)	0.0047 (12)	0.0006 (11)
C10	0.0399 (14)	0.0411 (15)	0.0544 (16)	−0.0018 (12)	0.0038 (12)	−0.0015 (12)
C11	0.0480 (16)	0.0392 (14)	0.0545 (16)	−0.0011 (12)	0.0132 (13)	0.0049 (12)
C12	0.0544 (17)	0.0531 (17)	0.0491 (15)	0.0055 (14)	0.0079 (13)	0.0095 (13)
C13	0.0446 (15)	0.0510 (16)	0.0519 (16)	0.0013 (13)	0.0005 (12)	0.0058 (13)
C14	0.0407 (15)	0.075 (2)	0.0496 (16)	0.0070 (14)	0.0036 (12)	0.0078 (15)
C15	0.0413 (15)	0.0687 (19)	0.0446 (15)	0.0058 (14)	0.0084 (12)	0.0073 (14)
C16	0.0589 (18)	0.077 (2)	0.0512 (17)	0.0058 (16)	0.0117 (14)	0.0091 (16)
C17	0.067 (2)	0.069 (2)	0.075 (2)	0.0072 (17)	0.0198 (17)	0.0153 (18)
C18	0.0606 (19)	0.078 (2)	0.070 (2)	0.0016 (17)	0.0130 (16)	−0.0064 (18)
C19	0.0544 (18)	0.089 (2)	0.0519 (17)	0.0091 (17)	0.0009 (14)	−0.0013 (18)
C20	0.0517 (16)	0.069 (2)	0.0442 (16)	0.0088 (15)	0.0039 (13)	0.0126 (14)
C21	0.0395 (14)	0.0584 (17)	0.0399 (14)	0.0102 (13)	0.0087 (11)	0.0115 (13)
C22	0.0455 (15)	0.0498 (16)	0.0459 (15)	0.0095 (13)	0.0096 (12)	0.0142 (13)
C23	0.0443 (15)	0.0559 (17)	0.0440 (15)	0.0046 (13)	0.0080 (11)	0.0074 (13)
C24	0.0393 (14)	0.0624 (18)	0.0375 (14)	0.0067 (13)	0.0046 (11)	0.0108 (13)
C25	0.0495 (16)	0.0574 (18)	0.0499 (16)	0.0083 (14)	0.0100 (12)	0.0202 (14)
C26	0.0513 (16)	0.0526 (16)	0.0499 (16)	0.0066 (13)	0.0063 (12)	0.0082 (13)

Geometric parameters (Å, º) top

Cl1—C1	1.745 (2)	C5—H5	0.9300
Cl2—C14	1.733 (3)	C6—H6A	0.9300
O1—N3	1.229 (3)	C7—H7	0.9300
O2—N3	1.222 (3)	C8—C13	1.409 (3)
O3—N4	1.214 (3)	C8—C9	1.413 (3)
O4—N4	1.220 (3)	C9—C10	1.391 (3)
O5—N7	1.202 (3)	C10—C11	1.361 (3)
O6—N7	1.211 (3)	C10—H10	0.9300
O7—N8	1.224 (3)	C11—C12	1.385 (4)
O8—N8	1.221 (3)	C12—C13	1.367 (3)
N1—C7	1.272 (3)	C12—H12	0.9300
N1—N2	1.368 (3)	C13—H13	0.9300
N2—C8	1.354 (3)	C14—C19	1.379 (4)
N2—H2	0.8600	C14—C15	1.399 (4)
N3—O1	1.229 (3)	C15—C16	1.389 (4)
N3—C9	1.445 (3)	C15—C20	1.456 (4)
N4—C11	1.464 (3)	C16—C17	1.374 (4)
N5—C20	1.275 (3)	C16—H16	0.9300
N5—N6	1.367 (3)	C17—C18	1.389 (4)
N6—C21	1.354 (3)	C17—H17	0.9300
N6—H6	0.8600	C18—C19	1.372 (4)
N7—O6	1.211 (3)	C18—H18	0.9300
N7—C22	1.443 (3)	C19—H19	0.9300
N8—C24	1.456 (3)	C20—H20	0.9300
C1—C6	1.377 (3)	C21—C26	1.410 (4)
C1—C2	1.396 (3)	C21—C22	1.414 (4)
C2—C3	1.389 (3)	C22—C23	1.380 (3)
C2—C7	1.457 (3)	C23—C24	1.362 (4)
C3—C4	1.375 (4)	C23—H23	0.9300
C3—H3	0.9300	C24—C25	1.386 (4)
C4—C5	1.379 (4)	C25—C26	1.363 (4)
C4—H4	0.9300	C25—H25	0.9300
C5—C6	1.376 (4)	C26—H26	0.9300

C7—N1—N2	115.0 (2)	C11—C10—C9	118.5 (2)
C8—N2—N1	120.0 (2)	C11—C10—H10	120.7
C8—N2—H2	120.0	C9—C10—H10	120.7
N1—N2—H2	120.0	C10—C11—C12	122.1 (2)
O2—N3—O1	121.8 (2)	C10—C11—N4	118.6 (2)
O2—N3—O1	121.8 (2)	C12—C11—N4	119.3 (2)
O2—N3—C9	118.9 (2)	C13—C12—C11	119.4 (2)
O1—N3—C9	119.2 (2)	C13—C12—H12	120.3
O1—N3—C9	119.2 (2)	C11—C12—H12	120.3
O3—N4—O4	123.9 (3)	C12—C13—C8	121.5 (2)
O3—N4—C11	117.9 (3)	C12—C13—H13	119.3
O4—N4—C11	118.2 (3)	C8—C13—H13	119.3
C20—N5—N6	116.6 (2)	C19—C14—C15	121.8 (3)
C21—N6—N5	119.6 (2)	C19—C14—Cl2	117.5 (2)
C21—N6—H6	120.2	C15—C14—Cl2	120.7 (2)
N5—N6—H6	120.2	C16—C15—C14	117.1 (3)
O5—N7—O6	120.9 (2)	C16—C15—C20	121.2 (3)
O5—N7—O6	120.9 (2)	C14—C15—C20	121.7 (3)
O5—N7—C22	119.6 (2)	C17—C16—C15	121.6 (3)
O6—N7—C22	119.4 (3)	C17—C16—H16	119.2
O6—N7—C22	119.4 (3)	C15—C16—H16	119.2
O8—N8—O7	123.5 (3)	C16—C17—C18	120.0 (3)
O8—N8—C24	118.0 (3)	C16—C17—H17	120.0
O7—N8—C24	118.5 (3)	C18—C17—H17	120.0
C6—C1—C2	121.8 (2)	C19—C18—C17	119.8 (3)
C6—C1—Cl1	118.19 (19)	C19—C18—H18	120.1
C2—C1—Cl1	119.98 (19)	C17—C18—H18	120.1
C3—C2—C1	117.3 (2)	C18—C19—C14	119.7 (3)
C3—C2—C7	120.8 (2)	C18—C19—H19	120.2
C1—C2—C7	121.9 (2)	C14—C19—H19	120.2
C4—C3—C2	121.3 (2)	N5—C20—C15	120.2 (3)
C4—C3—H3	119.4	N5—C20—H20	119.9
C2—C3—H3	119.4	C15—C20—H20	119.9
C3—C4—C5	120.1 (3)	N6—C21—C26	120.1 (3)
C3—C4—H4	120.0	N6—C21—C22	123.4 (2)
C5—C4—H4	120.0	C26—C21—C22	116.5 (2)
C6—C5—C4	120.2 (3)	C23—C22—C21	121.7 (2)
C6—C5—H5	119.9	C23—C22—N7	115.8 (2)
C4—C5—H5	119.9	C21—C22—N7	122.5 (2)
C1—C6—C5	119.3 (2)	C24—C23—C22	119.3 (3)
C1—C6—H6A	120.3	C24—C23—H23	120.4
C5—C6—H6A	120.3	C22—C23—H23	120.4
N1—C7—C2	120.9 (2)	C23—C24—C25	121.1 (2)
N1—C7—H7	119.6	C23—C24—N8	119.0 (3)
C2—C7—H7	119.6	C25—C24—N8	119.8 (2)
N2—C8—C13	120.4 (2)	C26—C25—C24	119.9 (2)
N2—C8—C9	122.8 (2)	C26—C25—H25	120.0
C13—C8—C9	116.8 (2)	C24—C25—H25	120.0
C10—C9—C8	121.7 (2)	C25—C26—C21	121.4 (3)
C10—C9—N3	116.1 (2)	C25—C26—H26	119.3
C8—C9—N3	122.3 (2)	C21—C26—H26	119.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···O6	0.86	2.02	2.631 (3)	127
N2—H2···O1	0.86	2.00	2.622 (3)	129

Experimental details

Crystal data
Chemical formula	C₁₃H₉ClN₄O₄
M_r	320.69
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.2286 (7), 7.6596 (8), 25.145 (2)
α, β, γ (°)	95.691 (2), 93.030 (2), 99.728 (3)
V (Å³)	1362.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.15 × 0.12 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.956, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	7216, 4776, 3273
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.125, 1.07
No. of reflections	4776
No. of parameters	397
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.36

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···O6	0.86	2.02	2.631 (3)	127
N2—H2···O1	0.86	2.00	2.622 (3)	129

Acknowledgements

This project was supported by the Postgraduate Foundation of Taishan University (grant No. Y04-2-08).

References

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