2-Chloro-N'-(4-nitro-benzyl-idene)benzo-hydrazide.

The title Schiff base compound, C(14)H(10)ClN(3)O(3), exists in a trans configuration with respect to the C=N bond. The dihedral angle between the two benzene rings is 15.9 (2)°. In the crystal, the mol-ecules are linked into chains along [101] by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For the biological properties of Schiff bases, see: Mohamed et al. (2009 ▶); Ritter et al. (2009 ▶); Bagihalli et al. (2008 ▶). For the crystal structures of Schiff base compounds, see: Fun et al. (2008 ▶); Shafiq et al. (2009 ▶); Goh et al. (2010 ▶). For other related structures, see: Zhou et al. (2009 ▶); Zhou & Yang (2009 ▶).

Experimental

Crystal data

C14H10ClN3O3

M = 303.70

Monoclinic,

a = 7.2752 (3) Å

b = 26.4081 (9) Å

c = 7.7284 (3) Å

β = 113.000 (2)°

V = 1366.78 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 298 K

0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.936, T max = 0.944

7876 measured reflections

2763 independent reflections

1934 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.113

S = 1.03

2763 reflections

193 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.27 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/S1600536809055330/ci5003sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055330/ci5003Isup2.hkl

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

C14H10ClN3O3	F(000) = 624
Mr = 303.70	Dx = 1.476 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1518 reflections
a = 7.2752 (3) Å	θ = 2.4–24.5°
b = 26.4081 (9) Å	µ = 0.29 mm−1
c = 7.7284 (3) Å	T = 298 K
β = 113.000 (2)°	Block, colourless
V = 1366.78 (9) Å3	0.23 × 0.20 × 0.20 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	2763 independent reflections
Radiation source: fine-focus sealed tube	1934 reflections with I > 2σ(I)
graphite	Rint = 0.036
ω scans	θmax = 26.3°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.936, Tmax = 0.944	k = −29→32
7876 measured reflections	l = −9→9

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0488P)2 + 0.233P] where P = (Fo2 + 2Fc2)/3
2763 reflections	(Δ/σ)max = 0.003
193 parameters	Δρmax = 0.19 e Å−3
1 restraint	Δρmin = −0.27 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	0.25382 (9)	0.09582 (2)	0.73742 (9)	0.0617 (2)
N1	0.2283 (2)	0.28721 (7)	0.5887 (2)	0.0434 (4)
N2	0.2675 (2)	0.25629 (7)	0.7434 (2)	0.0437 (4)
N3	0.2493 (3)	0.47567 (8)	0.0679 (3)	0.0637 (6)
O1	0.2747 (4)	0.52006 (8)	0.1124 (3)	0.1069 (8)
O2	0.2156 (4)	0.46052 (8)	−0.0899 (3)	0.0983 (7)
O3	0.0453 (2)	0.19654 (5)	0.57474 (19)	0.0498 (4)
C1	0.2747 (3)	0.36895 (8)	0.4821 (3)	0.0388 (5)
C2	0.3001 (3)	0.42028 (8)	0.5248 (3)	0.0505 (6)
H2	0.3247	0.4311	0.6464	0.061*
C3	0.2892 (3)	0.45526 (8)	0.3895 (3)	0.0525 (6)
H3	0.3032	0.4896	0.4176	0.063*
C4	0.2573 (3)	0.43846 (8)	0.2119 (3)	0.0447 (5)
C5	0.2344 (3)	0.38808 (8)	0.1647 (3)	0.0469 (5)
H5	0.2143	0.3776	0.0438	0.056*
C6	0.2420 (3)	0.35350 (8)	0.3006 (3)	0.0443 (5)
H6	0.2249	0.3193	0.2704	0.053*
C7	0.2910 (3)	0.33266 (8)	0.6288 (3)	0.0435 (5)
H7	0.3480	0.3427	0.7541	0.052*
C8	0.1706 (3)	0.21195 (8)	0.7239 (3)	0.0396 (5)
C9	0.2232 (3)	0.18436 (8)	0.9059 (3)	0.0392 (5)
C10	0.2608 (3)	0.13269 (8)	0.9245 (3)	0.0452 (5)
C11	0.3086 (3)	0.10918 (10)	1.0973 (4)	0.0612 (7)
H11	0.3399	0.0749	1.1108	0.073*
C12	0.3095 (4)	0.13687 (12)	1.2487 (4)	0.0680 (8)
H12	0.3372	0.1207	1.3631	0.082*
C13	0.2705 (4)	0.18759 (11)	1.2333 (3)	0.0623 (7)
H13	0.2722	0.2058	1.3369	0.075*
C14	0.2289 (3)	0.21163 (9)	1.0648 (3)	0.0496 (6)
H14	0.2042	0.2463	1.0553	0.060*
H2A	0.359 (3)	0.2671 (9)	0.853 (2)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0603 (4)	0.0542 (4)	0.0718 (4)	0.0013 (3)	0.0270 (3)	−0.0108 (3)
N1	0.0437 (10)	0.0494 (11)	0.0319 (9)	−0.0017 (8)	0.0091 (7)	0.0068 (8)
N2	0.0462 (10)	0.0469 (10)	0.0281 (9)	−0.0076 (8)	0.0039 (7)	0.0049 (8)
N3	0.0825 (15)	0.0591 (14)	0.0531 (13)	0.0030 (11)	0.0302 (11)	0.0129 (11)
O1	0.197 (3)	0.0488 (12)	0.0902 (16)	−0.0089 (14)	0.0720 (17)	0.0117 (11)
O2	0.160 (2)	0.0860 (15)	0.0546 (12)	−0.0099 (14)	0.0489 (13)	0.0119 (11)
O3	0.0535 (9)	0.0502 (9)	0.0318 (8)	−0.0070 (7)	0.0017 (7)	0.0008 (7)
C1	0.0362 (10)	0.0422 (12)	0.0357 (11)	0.0003 (9)	0.0117 (9)	0.0005 (9)
C2	0.0632 (14)	0.0485 (13)	0.0383 (12)	−0.0032 (11)	0.0182 (10)	−0.0059 (10)
C3	0.0667 (15)	0.0382 (12)	0.0521 (14)	−0.0037 (10)	0.0228 (11)	−0.0026 (10)
C4	0.0457 (12)	0.0454 (12)	0.0444 (12)	0.0019 (10)	0.0190 (10)	0.0082 (10)
C5	0.0524 (13)	0.0518 (13)	0.0360 (11)	0.0026 (11)	0.0167 (10)	−0.0014 (10)
C6	0.0502 (12)	0.0402 (11)	0.0407 (12)	0.0004 (9)	0.0156 (10)	−0.0030 (10)
C7	0.0436 (12)	0.0493 (13)	0.0337 (11)	−0.0019 (10)	0.0108 (9)	−0.0021 (9)
C8	0.0395 (11)	0.0454 (12)	0.0303 (10)	0.0019 (9)	0.0096 (9)	0.0013 (9)
C9	0.0333 (10)	0.0472 (13)	0.0329 (10)	−0.0032 (9)	0.0084 (8)	0.0005 (9)
C10	0.0351 (11)	0.0488 (13)	0.0479 (13)	−0.0033 (9)	0.0120 (9)	0.0057 (10)
C11	0.0505 (14)	0.0609 (16)	0.0635 (16)	−0.0018 (11)	0.0129 (12)	0.0220 (13)
C12	0.0601 (15)	0.090 (2)	0.0450 (15)	−0.0131 (14)	0.0106 (12)	0.0225 (15)
C13	0.0604 (15)	0.089 (2)	0.0369 (13)	−0.0178 (14)	0.0182 (11)	−0.0050 (13)
C14	0.0478 (12)	0.0586 (14)	0.0399 (12)	−0.0076 (11)	0.0145 (10)	0.0018 (11)

Cl1—C10	1.727 (2)	C4—C5	1.372 (3)
N1—C7	1.278 (3)	C5—C6	1.377 (3)
N1—N2	1.382 (2)	C5—H5	0.93
N2—C8	1.344 (3)	C6—H6	0.93
N2—H2A	0.895 (10)	C7—H7	0.93
N3—O2	1.214 (3)	C8—C9	1.495 (3)
N3—O1	1.215 (3)	C9—C10	1.388 (3)
N3—C4	1.468 (3)	C9—C14	1.410 (3)
O3—C8	1.226 (2)	C10—C11	1.388 (3)
C1—C6	1.389 (3)	C11—C12	1.378 (4)
C1—C2	1.390 (3)	C11—H11	0.93
C1—C7	1.454 (3)	C12—C13	1.365 (4)
C2—C3	1.374 (3)	C12—H12	0.93
C2—H2	0.93	C13—C14	1.372 (3)
C3—C4	1.373 (3)	C13—H13	0.93
C3—H3	0.93	C14—H14	0.93
C7—N1—N2	114.29 (16)	N1—C7—C1	121.13 (18)
C8—N2—N1	119.69 (15)	N1—C7—H7	119.4
C8—N2—H2A	123.1 (17)	C1—C7—H7	119.4
N1—N2—H2A	117.2 (17)	O3—C8—N2	124.00 (18)
O2—N3—O1	123.4 (2)	O3—C8—C9	123.06 (18)
O2—N3—C4	118.2 (2)	N2—C8—C9	112.86 (16)
O1—N3—C4	118.3 (2)	C10—C9—C14	118.30 (18)
C6—C1—C2	118.74 (19)	C10—C9—C8	122.97 (18)
C6—C1—C7	121.58 (19)	C14—C9—C8	118.69 (18)
C2—C1—C7	119.64 (19)	C11—C10—C9	120.3 (2)
C3—C2—C1	120.8 (2)	C11—C10—Cl1	117.86 (19)
C3—C2—H2	119.6	C9—C10—Cl1	121.83 (16)
C1—C2—H2	119.6	C12—C11—C10	119.7 (2)
C4—C3—C2	118.7 (2)	C12—C11—H11	120.1
C4—C3—H3	120.6	C10—C11—H11	120.1
C2—C3—H3	120.6	C13—C12—C11	121.0 (2)
C5—C4—C3	122.3 (2)	C13—C12—H12	119.5
C5—C4—N3	118.8 (2)	C11—C12—H12	119.5
C3—C4—N3	118.8 (2)	C12—C13—C14	119.9 (2)
C4—C5—C6	118.4 (2)	C12—C13—H13	120.1
C4—C5—H5	120.8	C14—C13—H13	120.1
C6—C5—H5	120.8	C13—C14—C9	120.7 (2)
C5—C6—C1	121.0 (2)	C13—C14—H14	119.6
C5—C6—H6	119.5	C9—C14—H14	119.6
C1—C6—H6	119.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3i	0.90 (1)	1.97 (1)	2.855 (2)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3i	0.90 (1)	1.97 (1)	2.855 (2)	169 (2)

Symmetry code: (i) .