2,4-Dichloro­benzaldehyde 2,4-dinitro­phenyl­hydrazone

Bao, F.

doi:10.1107/S1600536808020266

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1433

doi:10.1107/S1600536808020266

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2,4-Dichlorobenzaldehyde 2,4-dinitrophenylhydrazone

Feng-yu Bao ^a ^*

^aDepartment of Applied Chemistry, College of Sciences, Henan Agricultural University, Zhengzhou 450002, People's Republic of China
^*Correspondence e-mail: bfyu2008@yahoo.com.cn

(Received 4 June 2008; accepted 2 July 2008; online 9 July 2008)

The asymmetric unit of the title compound, C₁₃H₈Cl₂N₄O₄, contains two independent but similar and almost planar molecules. An intramolecular N—H⋯O hydrogen bond is observed in each molecule.

Related literature

For background, see: Okabe et al. (1993 ); Ohba (1996 ).

Experimental

Crystal data

C₁₃H₈Cl₂N₄O₄
M_r = 355.14
Monoclinic, P 2₁ /c
a = 13.3814 (7) Å
b = 28.9980 (13) Å
c = 7.3996 (3) Å
β = 92.422 (4)°
V = 2868.7 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.48 mm⁻¹
T = 291 (2) K
0.16 × 0.11 × 0.09 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.927, T_max = 0.958
21827 measured reflections
5060 independent reflections
2794 reflections with I > 2σ(I)
R_int = 0.092

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.187
S = 1.02
5060 reflections
415 parameters
H-atom parameters constrained
Δρ_max = 0.70 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—H6A⋯O3	0.86	2.05	2.645 (5)	126
N8—H8A⋯O8	0.86	2.03	2.627 (5)	126

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020266/hb2743sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808020266/hb2743Isup2.hkl

checkCIF report

Comment top

Several phenylhydrazone derivatives have been shown to be potentially DNA-damaging and are mutagenic agents (Okabe et al.,1993). As part of our work in this area, we have synthesized the title compound, (I), and we report its crystal structure here.

The two molecules in the asymmetric unit of (I) are almost planar, the dihedral angles between the the dichlorobenzene ring and the dinitrobenzene ring are 4.4 (2)° and 3.7 (2)°, in the C1 and C14 molecules, respectively. Otherwise, bond lengths and angles agree with those of other dinitrophenylhydrazone derivatives (Ohba, 1996). Intramolecular N—H···O hydrogen bonds (Fig. 1, Table 1) help to establish these molecular conformations.

Related literature top

For background, see: Okabe et al. (1993); Ohba (1996).

Experimental top

2,4-Dinitrophenylhydrazine (1 mmol, 0.198 g) was dissolved in anhydrous methanol, H₂SO₄ (98% 0.5 ml) was added to this, the mixture was stirred for several minitutes at 351 K, then 2,4-dichlorobenzyaldehyde (1 mmol, 0.175 g) in methanol (8 ml) was added dropwise and the mixture was stirred at refluxing temperature for 2 h. The product was isolated and recrystallized from DMF, yielding brown blocks of (I) after 6 d.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (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 30% probability level (arbitrary spheres for the H atoms). The hydrogen bonds are indicated by dashed lines.

2,4-Dichlorobenzaldehyde 2,4-dinitrophenylhydrazone top

Crystal data top

C₁₃H₈Cl₂N₄O₄	F(000) = 1440
M_r = 355.14	D_x = 1.645 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 721 reflections
a = 13.3814 (7) Å	θ = 2.5–20.6°
b = 28.9980 (13) Å	µ = 0.48 mm⁻¹
c = 7.3996 (3) Å	T = 291 K
β = 92.422 (4)°	Block, brown
V = 2868.7 (2) Å³	0.16 × 0.11 × 0.09 mm
Z = 8

Data collection top

Bruker SMART APEX CCD diffractometer	5060 independent reflections
Radiation source: sealed tube	2794 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.093
ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −15→15
T_min = 0.927, T_max = 0.958	k = −34→34
21827 measured reflections	l = −8→8

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.187	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0939P)²] where P = (F_o² + 2F_c²)/3
5060 reflections	(Δ/σ)_max = 0.018
415 parameters	Δρ_max = 0.70 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₃H₈Cl₂N₄O₄	V = 2868.7 (2) Å³
M_r = 355.14	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.3814 (7) Å	µ = 0.48 mm⁻¹
b = 28.9980 (13) Å	T = 291 K
c = 7.3996 (3) Å	0.16 × 0.11 × 0.09 mm
β = 92.422 (4)°

Data collection top

Bruker SMART APEX CCD diffractometer	5060 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2794 reflections with I > 2σ(I)
T_min = 0.927, T_max = 0.958	R_int = 0.093
21827 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.187	H-atom parameters constrained
S = 1.02	Δρ_max = 0.70 e Å⁻³
5060 reflections	Δρ_min = −0.36 e Å⁻³
415 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
C1	0.5169 (3)	0.79565 (15)	0.8938 (6)	0.0525 (11)
C2	0.4504 (4)	0.76034 (15)	0.8543 (6)	0.0568 (12)
H2A	0.4681	0.7299	0.8798	0.068*
C3	0.3594 (4)	0.77030 (16)	0.7782 (6)	0.0567 (12)
C4	0.3307 (4)	0.81536 (17)	0.7419 (7)	0.0649 (13)
H4A	0.2670	0.8217	0.6926	0.078*
C5	0.3956 (4)	0.85013 (17)	0.7786 (6)	0.0630 (13)
H5A	0.3755	0.8802	0.7532	0.076*
C6	0.4926 (4)	0.84239 (14)	0.8539 (6)	0.0508 (11)
C7	0.5828 (4)	0.95479 (14)	0.8532 (6)	0.0522 (11)
H7A	0.6458	0.9503	0.9085	0.063*
C8	0.5499 (3)	1.00103 (14)	0.7955 (5)	0.0483 (11)
C9	0.4563 (3)	1.00735 (15)	0.7104 (6)	0.0526 (11)
H9A	0.4151	0.9818	0.6913	0.063*
C10	0.4222 (3)	1.05004 (15)	0.6533 (6)	0.0535 (11)
H10A	0.3595	1.0534	0.5959	0.064*
C11	0.4836 (4)	1.08737 (14)	0.6836 (6)	0.0495 (11)
C12	0.5769 (3)	1.08302 (15)	0.7673 (6)	0.0519 (11)
H12A	0.6181	1.1086	0.7848	0.062*
C13	0.6078 (3)	1.03998 (14)	0.8247 (6)	0.0496 (11)
C14	0.0562 (3)	0.40012 (14)	0.2229 (5)	0.0453 (10)
C15	−0.0068 (3)	0.43582 (15)	0.1708 (6)	0.0501 (11)
H15A	0.0142	0.4662	0.1854	0.060*
C16	−0.1000 (3)	0.42650 (15)	0.0978 (6)	0.0509 (11)
C17	−0.1325 (4)	0.38143 (16)	0.0780 (6)	0.0572 (12)
H17A	−0.1972	0.3754	0.0330	0.069*
C18	−0.0705 (4)	0.34611 (16)	0.1240 (6)	0.0590 (12)
H18A	−0.0930	0.3160	0.1062	0.071*
C19	0.0269 (3)	0.35334 (14)	0.1980 (5)	0.0479 (11)
C20	0.1045 (4)	0.23951 (15)	0.2590 (6)	0.0535 (12)
H20A	0.1681	0.2440	0.3117	0.064*
C21	0.0647 (3)	0.19295 (14)	0.2269 (5)	0.0472 (11)
C22	0.1187 (3)	0.15381 (15)	0.2772 (5)	0.0506 (11)
C23	0.0818 (4)	0.10936 (14)	0.2470 (6)	0.0517 (11)
H23A	0.1193	0.0836	0.2818	0.062*
C24	−0.0113 (4)	0.10474 (15)	0.1644 (6)	0.0513 (11)
C25	−0.0668 (4)	0.14258 (16)	0.1099 (6)	0.0588 (12)
H25A	−0.1296	0.1388	0.0528	0.071*
C26	−0.0283 (4)	0.18613 (15)	0.1409 (6)	0.0552 (12)
H26A	−0.0657	0.2116	0.1031	0.066*
N1	0.1514 (3)	0.41294 (14)	0.3070 (5)	0.0577 (10)
N2	−0.1667 (3)	0.46460 (16)	0.0431 (5)	0.0612 (11)
N3	0.2910 (3)	0.73221 (16)	0.7304 (6)	0.0708 (12)
N4	0.6139 (3)	0.78294 (14)	0.9750 (6)	0.0659 (11)
N5	0.5238 (3)	0.92107 (12)	0.8261 (5)	0.0546 (10)
N6	0.5553 (3)	0.87810 (12)	0.8820 (5)	0.0541 (10)
H6A	0.6134	0.8742	0.9336	0.065*
N7	0.0487 (3)	0.27372 (12)	0.2123 (5)	0.0529 (10)
N8	0.0870 (3)	0.31688 (11)	0.2431 (5)	0.0532 (9)
H8A	0.1465	0.3208	0.2890	0.064*
O1	0.2127 (3)	0.74172 (14)	0.6467 (6)	0.0950 (13)
O2	0.3142 (3)	0.69353 (13)	0.7743 (6)	0.0985 (13)
O3	0.6762 (3)	0.81245 (11)	1.0089 (5)	0.0726 (10)
O4	0.6286 (3)	0.74302 (14)	1.0074 (8)	0.135 (2)
O5	−0.1387 (3)	0.50380 (12)	0.0700 (5)	0.0796 (11)
O6	−0.2487 (3)	0.45419 (12)	−0.0264 (5)	0.0833 (11)
O7	0.1687 (3)	0.45318 (12)	0.3374 (6)	0.0913 (13)
O8	0.2111 (3)	0.38253 (11)	0.3504 (5)	0.0731 (10)
Cl1	0.44331 (10)	1.14207 (4)	0.61744 (18)	0.0689 (4)
Cl2	−0.05792 (11)	0.04957 (4)	0.12777 (17)	0.0700 (4)
Cl3	0.23487 (9)	0.15728 (4)	0.38772 (18)	0.0705 (4)
Cl4	0.72292 (10)	1.03677 (4)	0.94132 (19)	0.0724 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.054 (3)	0.047 (3)	0.057 (3)	0.004 (2)	0.000 (2)	−0.002 (2)
C2	0.061 (3)	0.041 (3)	0.069 (3)	0.001 (2)	0.002 (3)	0.002 (2)
C3	0.055 (3)	0.052 (3)	0.064 (3)	−0.006 (2)	0.004 (2)	0.004 (2)
C4	0.054 (3)	0.060 (3)	0.080 (3)	0.007 (3)	−0.005 (3)	0.012 (3)
C5	0.066 (3)	0.049 (3)	0.073 (3)	0.002 (3)	−0.005 (3)	0.008 (2)
C6	0.061 (3)	0.038 (3)	0.053 (3)	0.000 (2)	0.005 (2)	−0.0013 (19)
C7	0.058 (3)	0.045 (3)	0.053 (3)	0.001 (2)	0.004 (2)	0.002 (2)
C8	0.050 (3)	0.047 (3)	0.048 (2)	0.001 (2)	0.003 (2)	0.0021 (19)
C9	0.055 (3)	0.048 (3)	0.055 (3)	−0.011 (2)	−0.001 (2)	0.000 (2)
C10	0.050 (3)	0.055 (3)	0.055 (3)	0.001 (2)	−0.002 (2)	0.008 (2)
C11	0.060 (3)	0.039 (2)	0.050 (3)	0.004 (2)	0.003 (2)	0.0070 (19)
C12	0.054 (3)	0.045 (3)	0.057 (3)	−0.002 (2)	0.003 (2)	0.006 (2)
C13	0.048 (3)	0.048 (3)	0.052 (3)	−0.002 (2)	−0.005 (2)	0.003 (2)
C14	0.051 (3)	0.044 (2)	0.041 (2)	−0.003 (2)	0.003 (2)	−0.0004 (18)
C15	0.055 (3)	0.044 (3)	0.051 (3)	−0.007 (2)	0.002 (2)	−0.003 (2)
C16	0.052 (3)	0.048 (3)	0.053 (3)	0.000 (2)	0.004 (2)	0.003 (2)
C17	0.051 (3)	0.058 (3)	0.062 (3)	−0.008 (2)	−0.007 (2)	−0.001 (2)
C18	0.063 (3)	0.048 (3)	0.066 (3)	−0.010 (2)	−0.002 (3)	−0.002 (2)
C19	0.053 (3)	0.046 (3)	0.045 (2)	−0.006 (2)	0.003 (2)	0.0022 (19)
C20	0.062 (3)	0.047 (3)	0.052 (3)	−0.004 (2)	0.002 (2)	0.000 (2)
C21	0.056 (3)	0.044 (3)	0.042 (2)	0.004 (2)	0.003 (2)	0.0053 (18)
C22	0.054 (3)	0.055 (3)	0.043 (2)	0.001 (2)	0.002 (2)	−0.0008 (19)
C23	0.059 (3)	0.042 (3)	0.054 (3)	0.006 (2)	−0.002 (2)	0.006 (2)
C24	0.058 (3)	0.051 (3)	0.044 (2)	−0.006 (2)	−0.001 (2)	0.001 (2)
C25	0.058 (3)	0.064 (3)	0.053 (3)	−0.001 (3)	−0.008 (2)	0.003 (2)
C26	0.066 (3)	0.045 (3)	0.054 (3)	−0.004 (2)	−0.003 (2)	0.003 (2)
N1	0.058 (3)	0.049 (3)	0.065 (2)	−0.001 (2)	−0.007 (2)	−0.0022 (19)
N2	0.057 (3)	0.063 (3)	0.062 (2)	0.008 (2)	−0.008 (2)	0.007 (2)
N3	0.059 (3)	0.064 (3)	0.089 (3)	−0.011 (2)	0.000 (3)	0.002 (2)
N4	0.069 (3)	0.039 (2)	0.088 (3)	0.008 (2)	−0.014 (2)	0.006 (2)
N5	0.068 (3)	0.035 (2)	0.060 (2)	0.0043 (19)	0.0047 (19)	0.0060 (17)
N6	0.064 (3)	0.043 (2)	0.056 (2)	0.0031 (19)	0.0001 (19)	0.0027 (17)
N7	0.068 (3)	0.038 (2)	0.053 (2)	−0.0054 (19)	0.0012 (19)	−0.0002 (16)
N8	0.058 (2)	0.039 (2)	0.063 (2)	−0.0008 (18)	−0.0017 (19)	0.0015 (17)
O1	0.072 (3)	0.090 (3)	0.121 (3)	−0.011 (2)	−0.027 (3)	0.002 (2)
O2	0.085 (3)	0.053 (2)	0.157 (4)	−0.008 (2)	−0.013 (3)	0.006 (2)
O3	0.069 (2)	0.052 (2)	0.096 (3)	−0.0040 (18)	−0.019 (2)	−0.0004 (17)
O4	0.094 (3)	0.048 (3)	0.256 (6)	0.001 (2)	−0.075 (4)	0.023 (3)
O5	0.087 (3)	0.046 (2)	0.105 (3)	0.0062 (19)	−0.012 (2)	0.0089 (19)
O6	0.066 (3)	0.084 (3)	0.098 (3)	0.005 (2)	−0.016 (2)	0.007 (2)
O7	0.081 (3)	0.047 (2)	0.142 (4)	−0.0054 (19)	−0.036 (3)	−0.012 (2)
O8	0.070 (2)	0.053 (2)	0.095 (3)	0.0059 (18)	−0.019 (2)	−0.0025 (18)
Cl1	0.0721 (9)	0.0489 (7)	0.0843 (9)	0.0067 (6)	−0.0118 (7)	0.0137 (6)
Cl2	0.0824 (10)	0.0512 (7)	0.0750 (8)	−0.0133 (6)	−0.0150 (7)	−0.0007 (6)
Cl3	0.0564 (8)	0.0704 (9)	0.0833 (9)	−0.0032 (6)	−0.0139 (7)	−0.0004 (6)
Cl4	0.0567 (8)	0.0676 (8)	0.0911 (9)	−0.0022 (6)	−0.0189 (7)	0.0157 (7)

Geometric parameters (Å, º) top

C1—C2	1.379 (6)	C16—N2	1.467 (6)
C1—C6	1.422 (6)	C17—C18	1.352 (6)
C1—N4	1.455 (6)	C17—H17A	0.9300
C2—C3	1.352 (6)	C18—C19	1.408 (6)
C2—H2A	0.9300	C18—H18A	0.9300
C3—C4	1.385 (6)	C19—N8	1.361 (5)
C3—N3	1.468 (6)	C20—N7	1.280 (5)
C4—C5	1.351 (7)	C20—C21	1.467 (6)
C4—H4A	0.9300	C20—H20A	0.9300
C5—C6	1.409 (7)	C21—C26	1.388 (6)
C5—H5A	0.9300	C21—C22	1.388 (6)
C6—N6	1.343 (5)	C22—C23	1.395 (6)
C7—N5	1.267 (5)	C22—Cl3	1.728 (5)
C7—C8	1.469 (6)	C23—C24	1.371 (6)
C7—H7A	0.9300	C23—H23A	0.9300
C8—C13	1.381 (6)	C24—C25	1.376 (6)
C8—C9	1.390 (6)	C24—Cl2	1.734 (4)
C9—C10	1.379 (6)	C25—C26	1.380 (6)
C9—H9A	0.9300	C25—H25A	0.9300
C10—C11	1.372 (6)	C26—H26A	0.9300
C10—H10A	0.9300	N1—O7	1.209 (4)
C11—C12	1.375 (6)	N1—O8	1.224 (5)
C11—Cl1	1.739 (4)	N2—O5	1.211 (5)
C12—C13	1.376 (6)	N2—O6	1.229 (5)
C12—H12A	0.9300	N3—O2	1.204 (5)
C13—Cl4	1.736 (5)	N3—O1	1.226 (5)
C14—C15	1.379 (6)	N4—O4	1.197 (5)
C14—C19	1.422 (6)	N4—O3	1.213 (5)
C14—N1	1.443 (6)	N5—N6	1.373 (5)
C15—C16	1.365 (6)	N6—H6A	0.8600
C15—H15A	0.9300	N7—N8	1.368 (5)
C16—C17	1.384 (6)	N8—H8A	0.8600

C2—C1—C6	121.6 (4)	C18—C17—H17A	119.9
C2—C1—N4	117.1 (4)	C16—C17—H17A	119.9
C6—C1—N4	121.3 (4)	C17—C18—C19	122.2 (4)
C3—C2—C1	119.4 (4)	C17—C18—H18A	118.9
C3—C2—H2A	120.3	C19—C18—H18A	118.9
C1—C2—H2A	120.3	N8—C19—C18	120.5 (4)
C2—C3—C4	121.3 (4)	N8—C19—C14	123.5 (4)
C2—C3—N3	118.7 (4)	C18—C19—C14	116.0 (4)
C4—C3—N3	119.9 (5)	N7—C20—C21	117.8 (4)
C5—C4—C3	119.6 (5)	N7—C20—H20A	121.1
C5—C4—H4A	120.2	C21—C20—H20A	121.1
C3—C4—H4A	120.2	C26—C21—C22	116.9 (4)
C4—C5—C6	122.3 (4)	C26—C21—C20	121.2 (4)
C4—C5—H5A	118.8	C22—C21—C20	121.9 (4)
C6—C5—H5A	118.8	C21—C22—C23	122.4 (4)
N6—C6—C5	119.8 (4)	C21—C22—Cl3	121.8 (3)
N6—C6—C1	124.6 (4)	C23—C22—Cl3	115.8 (3)
C5—C6—C1	115.6 (4)	C24—C23—C22	118.1 (4)
N5—C7—C8	118.7 (4)	C24—C23—H23A	120.9
N5—C7—H7A	120.6	C22—C23—H23A	120.9
C8—C7—H7A	120.6	C23—C24—C25	121.5 (4)
C13—C8—C9	116.8 (4)	C23—C24—Cl2	118.3 (3)
C13—C8—C7	122.8 (4)	C25—C24—Cl2	120.2 (4)
C9—C8—C7	120.4 (4)	C24—C25—C26	119.2 (4)
C10—C9—C8	122.5 (4)	C24—C25—H25A	120.4
C10—C9—H9A	118.8	C26—C25—H25A	120.4
C8—C9—H9A	118.8	C25—C26—C21	121.9 (4)
C9—C10—C11	118.0 (4)	C25—C26—H26A	119.0
C9—C10—H10A	121.0	C21—C26—H26A	119.0
C11—C10—H10A	121.0	O7—N1—O8	121.9 (4)
C12—C11—C10	121.8 (4)	O7—N1—C14	119.2 (4)
C12—C11—Cl1	118.4 (3)	O8—N1—C14	118.8 (4)
C10—C11—Cl1	119.8 (4)	O5—N2—O6	124.3 (4)
C11—C12—C13	118.5 (4)	O5—N2—C16	118.7 (4)
C11—C12—H12A	120.8	O6—N2—C16	116.9 (4)
C13—C12—H12A	120.8	O2—N3—O1	123.4 (5)
C12—C13—C8	122.3 (4)	O2—N3—C3	119.0 (5)
C12—C13—Cl4	116.8 (3)	O1—N3—C3	117.6 (4)
C8—C13—Cl4	120.9 (3)	O4—N4—O3	122.3 (4)
C15—C14—C19	121.2 (4)	O4—N4—C1	117.7 (4)
C15—C14—N1	116.4 (4)	O3—N4—C1	120.0 (4)
C19—C14—N1	122.4 (4)	C7—N5—N6	118.1 (4)
C16—C15—C14	119.9 (4)	C6—N6—N5	118.1 (4)
C16—C15—H15A	120.0	C6—N6—H6A	120.9
C14—C15—H15A	120.0	N5—N6—H6A	120.9
C15—C16—C17	120.5 (4)	C20—N7—N8	117.0 (4)
C15—C16—N2	119.7 (4)	C19—N8—N7	117.2 (4)
C17—C16—N2	119.8 (4)	C19—N8—H8A	121.4
C18—C17—C16	120.1 (4)	N7—N8—H8A	121.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···O3	0.86	2.05	2.645 (5)	126
N8—H8A···O8	0.86	2.03	2.627 (5)	126

Experimental details

Crystal data
Chemical formula	C₁₃H₈Cl₂N₄O₄
M_r	355.14
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	13.3814 (7), 28.9980 (13), 7.3996 (3)
β (°)	92.422 (4)
V (Å³)	2868.7 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.48
Crystal size (mm)	0.16 × 0.11 × 0.09

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.927, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	21827, 5060, 2794
R_int	0.093
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.187, 1.02
No. of reflections	5060
No. of parameters	415
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.36

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···O3	0.86	2.05	2.645 (5)	126
N8—H8A···O8	0.86	2.03	2.627 (5)	126

References

Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ohba, S. (1996). Acta Cryst. C52, 2118–2119. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Okabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678–1680. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 8| August 2008| Page o1433

doi:10.1107/S1600536808020266

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