(E)-N'-(2,4-Dichloro-benzyl-idene)-3-nitro-benzohydrazide.

The title compound, C(14)H(9)Cl(2)N(3)O(3), was prepared by the reaction of 3-nitro-benzohydrazide with 2,4-dichloro-benzalde-hyde. The mol-ecule adopts an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 4.6 (2)°. In the crystal, the hydrazone mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains along the c axis.

Related literature

For medical applications of hydrazones, see: Ajani et al. (2010 ▶); Zhang et al. (2010 ▶); Angelusiu et al. (2010 ▶). For related structures, see: Huang & Wu (2010 ▶); Khaledi et al. (2010 ▶); Zhou & Yang (2010 ▶); Ji & Lu (2010 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶). For similar compounds that we have reported recently, see: Dai & Mao (2010a ▶,b ▶).

Experimental

Crystal data

C14H9Cl2N3O3

M = 338.14

Monoclinic,

a = 12.004 (3) Å

b = 14.384 (3) Å

c = 8.465 (2) Å

β = 96.302 (2)°

V = 1452.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.46 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.913, T max = 0.921

11555 measured reflections

3163 independent reflections

2128 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.107

S = 1.05

3163 reflections

202 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810049470/sj5069sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049470/sj5069Isup2.hkl

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

C14H9Cl2N3O3	F(000) = 688
Mr = 338.14	Dx = 1.546 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2237 reflections
a = 12.004 (3) Å	θ = 2.3–24.5°
b = 14.384 (3) Å	µ = 0.46 mm−1
c = 8.465 (2) Å	T = 298 K
β = 96.302 (2)°	Block, yellow
V = 1452.8 (6) Å3	0.20 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3163 independent reflections
Radiation source: fine-focus sealed tube	2128 reflections with I > 2σ(I)
graphite	Rint = 0.038
ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→13
Tmin = 0.913, Tmax = 0.921	k = −18→18
11555 measured reflections	l = −10→10

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0467P)2 + 0.1033P] where P = (Fo2 + 2Fc2)/3
3163 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.22 e Å−3
1 restraint	Δρmin = −0.20 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
Cl1	0.26406 (6)	−0.09815 (4)	0.11977 (8)	0.0651 (2)
Cl2	0.49631 (6)	−0.18532 (5)	−0.36654 (9)	0.0760 (3)
N1	0.28128 (14)	0.18486 (11)	−0.03316 (19)	0.0344 (4)
N2	0.23633 (14)	0.25093 (11)	0.06051 (18)	0.0342 (4)
N3	0.12644 (17)	0.66091 (13)	0.0801 (3)	0.0542 (5)
O1	0.20635 (13)	0.34676 (9)	−0.15308 (16)	0.0454 (4)
O2	0.19086 (19)	0.67781 (12)	−0.0175 (3)	0.0808 (6)
O3	0.06980 (18)	0.71959 (12)	0.1368 (3)	0.0922 (7)
C1	0.33504 (17)	−0.06183 (14)	−0.0373 (3)	0.0385 (5)
C2	0.34878 (16)	0.03282 (13)	−0.0659 (2)	0.0330 (5)
C3	0.40982 (18)	0.05744 (14)	−0.1909 (2)	0.0394 (5)
H3	0.4201	0.1200	−0.2128	0.047*
C4	0.45528 (18)	−0.00914 (16)	−0.2829 (2)	0.0449 (5)
H4	0.4973	0.0084	−0.3640	0.054*
C5	0.43747 (18)	−0.10158 (15)	−0.2525 (3)	0.0446 (6)
C6	0.37757 (18)	−0.12984 (15)	−0.1318 (3)	0.0451 (6)
H6	0.3657	−0.1926	−0.1135	0.054*
C7	0.30075 (17)	0.10478 (13)	0.0282 (2)	0.0353 (5)
H7	0.2847	0.0923	0.1311	0.042*
C8	0.20044 (16)	0.33100 (13)	−0.0112 (2)	0.0320 (5)
C9	0.15054 (16)	0.40225 (13)	0.0894 (2)	0.0296 (4)
C10	0.16380 (16)	0.49489 (13)	0.0476 (2)	0.0340 (5)
H10	0.2056	0.5105	−0.0347	0.041*
C11	0.11400 (18)	0.56310 (14)	0.1300 (2)	0.0386 (5)
C12	0.05041 (19)	0.54271 (16)	0.2516 (3)	0.0490 (6)
H12	0.0173	0.5898	0.3054	0.059*
C13	0.03713 (19)	0.45074 (17)	0.2916 (3)	0.0477 (6)
H13	−0.0056	0.4356	0.3732	0.057*
C14	0.08693 (16)	0.38009 (15)	0.2110 (2)	0.0376 (5)
H14	0.0774	0.3183	0.2388	0.045*
H2	0.231 (2)	0.2398 (18)	0.1627 (14)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0776 (5)	0.0440 (4)	0.0797 (5)	−0.0040 (3)	0.0359 (4)	0.0085 (3)
Cl2	0.0832 (5)	0.0620 (4)	0.0845 (5)	0.0183 (4)	0.0174 (4)	−0.0351 (4)
N1	0.0418 (10)	0.0307 (9)	0.0318 (9)	0.0035 (8)	0.0095 (8)	−0.0038 (7)
N2	0.0493 (11)	0.0294 (9)	0.0259 (8)	0.0063 (8)	0.0126 (8)	0.0000 (7)
N3	0.0544 (14)	0.0335 (11)	0.0733 (15)	0.0013 (10)	0.0004 (11)	−0.0153 (10)
O1	0.0735 (11)	0.0371 (8)	0.0285 (8)	0.0118 (7)	0.0187 (7)	0.0037 (6)
O2	0.1069 (17)	0.0392 (10)	0.1022 (16)	−0.0029 (10)	0.0370 (14)	0.0029 (10)
O3	0.0933 (15)	0.0387 (10)	0.151 (2)	0.0116 (10)	0.0411 (14)	−0.0234 (12)
C1	0.0363 (12)	0.0334 (11)	0.0455 (12)	0.0019 (9)	0.0034 (10)	0.0002 (9)
C2	0.0334 (11)	0.0326 (11)	0.0324 (11)	0.0044 (9)	0.0011 (9)	−0.0038 (8)
C3	0.0489 (14)	0.0332 (11)	0.0365 (12)	0.0037 (10)	0.0059 (10)	−0.0011 (9)
C4	0.0486 (14)	0.0508 (14)	0.0365 (12)	0.0040 (11)	0.0098 (10)	−0.0078 (10)
C5	0.0425 (13)	0.0420 (13)	0.0484 (13)	0.0102 (10)	0.0013 (11)	−0.0168 (10)
C6	0.0474 (14)	0.0297 (11)	0.0568 (14)	0.0037 (10)	−0.0002 (12)	−0.0072 (10)
C7	0.0415 (13)	0.0348 (11)	0.0301 (11)	0.0036 (9)	0.0068 (9)	−0.0008 (8)
C8	0.0382 (12)	0.0286 (10)	0.0299 (11)	−0.0011 (9)	0.0066 (9)	−0.0021 (8)
C9	0.0300 (11)	0.0327 (11)	0.0258 (10)	0.0025 (8)	0.0024 (8)	−0.0012 (8)
C10	0.0338 (11)	0.0334 (11)	0.0351 (11)	−0.0003 (9)	0.0048 (9)	−0.0041 (8)
C11	0.0376 (12)	0.0341 (11)	0.0426 (12)	0.0050 (9)	−0.0017 (10)	−0.0076 (9)
C12	0.0478 (14)	0.0534 (15)	0.0460 (13)	0.0155 (11)	0.0054 (11)	−0.0160 (11)
C13	0.0452 (14)	0.0649 (16)	0.0355 (12)	0.0095 (12)	0.0155 (10)	−0.0011 (11)
C14	0.0391 (12)	0.0430 (12)	0.0315 (11)	0.0030 (10)	0.0070 (9)	0.0031 (9)

Cl1—C1	1.736 (2)	C4—C5	1.376 (3)
Cl2—C5	1.741 (2)	C4—H4	0.9300
N1—C7	1.275 (2)	C5—C6	1.374 (3)
N1—N2	1.384 (2)	C6—H6	0.9300
N2—C8	1.350 (2)	C7—H7	0.9300
N2—H2	0.889 (10)	C8—C9	1.499 (3)
N3—O3	1.215 (2)	C9—C14	1.384 (3)
N3—O2	1.216 (3)	C9—C10	1.392 (3)
N3—C11	1.481 (3)	C10—C11	1.378 (3)
O1—C8	1.232 (2)	C10—H10	0.9300
C1—C6	1.395 (3)	C11—C12	1.379 (3)
C1—C2	1.396 (3)	C12—C13	1.379 (3)
C2—C3	1.397 (3)	C12—H12	0.9300
C2—C7	1.463 (3)	C13—C14	1.395 (3)
C3—C4	1.383 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C7—N1—N2	116.89 (16)	N1—C7—C2	118.86 (18)
C8—N2—N1	116.96 (15)	N1—C7—H7	120.6
C8—N2—H2	122.3 (17)	C2—C7—H7	120.6
N1—N2—H2	120.7 (17)	O1—C8—N2	123.05 (17)
O3—N3—O2	123.7 (2)	O1—C8—C9	119.84 (17)
O3—N3—C11	117.9 (2)	N2—C8—C9	117.11 (17)
O2—N3—C11	118.37 (19)	C14—C9—C10	119.82 (18)
C6—C1—C2	121.8 (2)	C14—C9—C8	123.54 (17)
C6—C1—Cl1	117.98 (16)	C10—C9—C8	116.48 (17)
C2—C1—Cl1	120.26 (16)	C11—C10—C9	118.99 (19)
C1—C2—C3	117.44 (18)	C11—C10—H10	120.5
C1—C2—C7	122.28 (19)	C9—C10—H10	120.5
C3—C2—C7	120.28 (18)	C10—C11—C12	122.2 (2)
C4—C3—C2	121.5 (2)	C10—C11—N3	118.0 (2)
C4—C3—H3	119.2	C12—C11—N3	119.8 (2)
C2—C3—H3	119.2	C11—C12—C13	118.4 (2)
C5—C4—C3	119.0 (2)	C11—C12—H12	120.8
C5—C4—H4	120.5	C13—C12—H12	120.8
C3—C4—H4	120.5	C12—C13—C14	120.8 (2)
C6—C5—C4	122.0 (2)	C12—C13—H13	119.6
C6—C5—Cl2	119.02 (17)	C14—C13—H13	119.6
C4—C5—Cl2	118.97 (19)	C9—C14—C13	119.8 (2)
C5—C6—C1	118.3 (2)	C9—C14—H14	120.1
C5—C6—H6	120.9	C13—C14—H14	120.1
C1—C6—H6	120.9

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.89 (1)	2.04 (2)	2.859 (2)	152 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.89 (1)	2.04 (2)	2.859 (2)	152 (2)

Symmetry code: (i) .