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

In the title compound, C(14)H(10)ClN(3)O(3), the dihedral angle between the benzene rings is 6.64 (13)°. In the crystal, mol-ecules are linked through N-H⋯O hydrogen bonds, forming chains running along the c axis direction.

Related literature

For general background to hydrazones, see: Rasras et al. (2010 ▶); Pyta et al. (2010 ▶); Angelusiu et al. (2010 ▶). For related structures, see: Fun et al. (2008 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶); Tang (2010 ▶, 2011 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H10ClN3O3

M = 303.70

Monoclinic,

a = 11.2332 (18) Å

b = 13.3778 (18) Å

c = 8.9770 (16) Å

β = 90.408 (2)°

V = 1349.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 298 K

0.18 × 0.17 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.949, T max = 0.957

10640 measured reflections

2931 independent reflections

1882 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.146

S = 1.03

2931 reflections

193 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811055589/su2353sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055589/su2353Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811055589/su2353Isup3.cml

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

C14H10ClN3O3	F(000) = 624
Mr = 303.70	Dx = 1.495 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.2332 (18) Å	Cell parameters from 2464 reflections
b = 13.3778 (18) Å	θ = 2.4–24.5°
c = 8.9770 (16) Å	µ = 0.30 mm−1
β = 90.408 (2)°	T = 298 K
V = 1349.0 (4) Å3	Cut from needle, yellow
Z = 4	0.18 × 0.17 × 0.15 mm

Bruker SMART CCD area-detector diffractometer	2931 independent reflections
Radiation source: fine-focus sealed tube	1882 reflections with I > 2σ(I)
graphite	Rint = 0.045
ω scans	θmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.949, Tmax = 0.957	k = −14→17
10640 measured reflections	l = −11→11

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0569P)2 + 0.5874P] where P = (Fo2 + 2Fc2)/3
2931 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.36 e Å−3
1 restraint	Δρmin = −0.29 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	0.23505 (8)	0.62569 (6)	1.10065 (9)	0.0782 (3)
H2	0.246 (3)	0.265 (2)	1.1045 (13)	0.080*
N1	0.18950 (18)	0.33163 (14)	0.9198 (2)	0.0444 (5)
N2	0.23517 (19)	0.25548 (14)	1.0072 (2)	0.0446 (5)
N3	0.4488 (2)	−0.1478 (2)	1.3026 (3)	0.0667 (7)
O1	0.26845 (19)	0.15983 (13)	0.80373 (18)	0.0620 (5)
O2	0.4173 (3)	−0.23176 (19)	1.2688 (3)	0.1126 (10)
O3	0.5111 (2)	−0.12928 (18)	1.4092 (3)	0.0902 (8)
C1	0.1488 (2)	0.59971 (19)	0.9450 (3)	0.0513 (6)
C2	0.1308 (2)	0.50090 (18)	0.8991 (3)	0.0452 (6)
C3	0.0625 (2)	0.4872 (2)	0.7698 (3)	0.0553 (7)
H3	0.0493	0.4227	0.7348	0.066*
C4	0.0149 (3)	0.5657 (3)	0.6941 (3)	0.0679 (8)
H4	−0.0312	0.5541	0.6094	0.082*
C5	0.0344 (3)	0.6622 (2)	0.7416 (4)	0.0709 (9)
H5	0.0020	0.7154	0.6885	0.085*
C6	0.1015 (3)	0.6800 (2)	0.8673 (4)	0.0644 (8)
H6	0.1149	0.7450	0.8998	0.077*
C7	0.1807 (2)	0.41629 (18)	0.9816 (3)	0.0463 (6)
H7	0.2061	0.4247	1.0796	0.056*
C8	0.2731 (2)	0.17126 (17)	0.9389 (3)	0.0434 (6)
C9	0.3213 (2)	0.09038 (17)	1.0373 (2)	0.0392 (5)
C10	0.3769 (2)	0.10957 (18)	1.1718 (3)	0.0443 (6)
H10	0.3845	0.1751	1.2052	0.053*
C11	0.4216 (2)	0.03155 (19)	1.2576 (3)	0.0495 (6)
H11	0.4605	0.0441	1.3474	0.059*
C12	0.4069 (2)	−0.06443 (19)	1.2070 (3)	0.0479 (6)
C13	0.3536 (2)	−0.08568 (19)	1.0728 (3)	0.0558 (7)
H13	0.3456	−0.1514	1.0404	0.067*
C14	0.3122 (2)	−0.00768 (19)	0.9871 (3)	0.0539 (7)
H14	0.2777	−0.0207	0.8947	0.065*

	U11	U22	U33	U12	U13	U23
Cl1	0.1009 (6)	0.0532 (5)	0.0802 (6)	−0.0085 (4)	−0.0221 (5)	−0.0047 (4)
N1	0.0560 (12)	0.0374 (11)	0.0397 (11)	−0.0027 (9)	−0.0030 (9)	0.0046 (9)
N2	0.0662 (13)	0.0345 (11)	0.0329 (11)	−0.0010 (9)	−0.0045 (9)	−0.0007 (9)
N3	0.0637 (15)	0.0569 (16)	0.0792 (18)	0.0213 (12)	−0.0113 (13)	0.0006 (14)
O1	0.1089 (16)	0.0463 (10)	0.0308 (10)	−0.0018 (10)	−0.0020 (9)	−0.0018 (8)
O2	0.134 (2)	0.0514 (15)	0.152 (3)	0.0189 (14)	−0.0636 (19)	0.0076 (15)
O3	0.1053 (18)	0.0902 (18)	0.0747 (16)	0.0349 (14)	−0.0268 (14)	−0.0009 (13)
C1	0.0545 (14)	0.0475 (15)	0.0518 (15)	−0.0003 (12)	0.0045 (12)	0.0070 (12)
C2	0.0504 (13)	0.0428 (14)	0.0425 (14)	0.0001 (11)	0.0078 (11)	0.0052 (11)
C3	0.0590 (16)	0.0573 (17)	0.0496 (16)	0.0051 (13)	−0.0006 (12)	−0.0021 (13)
C4	0.0709 (19)	0.078 (2)	0.0548 (17)	0.0151 (16)	−0.0082 (14)	0.0057 (16)
C5	0.081 (2)	0.063 (2)	0.068 (2)	0.0191 (16)	0.0024 (17)	0.0202 (16)
C6	0.0742 (19)	0.0443 (16)	0.075 (2)	0.0044 (14)	0.0094 (16)	0.0094 (14)
C7	0.0579 (14)	0.0440 (14)	0.0369 (13)	−0.0017 (11)	−0.0019 (11)	0.0026 (11)
C8	0.0579 (14)	0.0369 (13)	0.0353 (13)	−0.0113 (11)	−0.0005 (10)	0.0003 (10)
C9	0.0476 (12)	0.0365 (12)	0.0337 (12)	−0.0051 (10)	0.0043 (10)	−0.0016 (10)
C10	0.0510 (13)	0.0369 (13)	0.0450 (14)	−0.0038 (10)	−0.0014 (11)	−0.0087 (11)
C11	0.0507 (14)	0.0530 (16)	0.0446 (14)	0.0034 (12)	−0.0080 (11)	−0.0057 (12)
C12	0.0468 (13)	0.0443 (14)	0.0526 (15)	0.0089 (11)	0.0004 (11)	0.0007 (12)
C13	0.0694 (17)	0.0355 (13)	0.0625 (18)	0.0044 (12)	−0.0095 (14)	−0.0119 (12)
C14	0.0749 (18)	0.0416 (14)	0.0450 (14)	−0.0001 (13)	−0.0130 (13)	−0.0117 (12)

Cl1—C1	1.729 (3)	C4—H4	0.9300
N1—C7	1.265 (3)	C5—C6	1.373 (4)
N1—N2	1.382 (3)	C5—H5	0.9300
N2—C8	1.353 (3)	C6—H6	0.9300
N2—H2	0.891 (10)	C7—H7	0.9300
N3—O3	1.207 (3)	C8—C9	1.495 (3)
N3—O2	1.216 (3)	C9—C10	1.380 (3)
N3—C12	1.482 (3)	C9—C14	1.390 (3)
O1—C8	1.224 (3)	C10—C11	1.389 (3)
C1—C6	1.385 (4)	C10—H10	0.9300
C1—C2	1.399 (3)	C11—C12	1.372 (3)
C2—C3	1.399 (3)	C11—H11	0.9300
C2—C7	1.462 (3)	C12—C13	1.371 (3)
C3—C4	1.358 (4)	C13—C14	1.375 (4)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.377 (5)	C14—H14	0.9300
C7—N1—N2	116.14 (19)	N1—C7—C2	120.1 (2)
C8—N2—N1	118.26 (19)	N1—C7—H7	119.9
C8—N2—H2	122 (2)	C2—C7—H7	119.9
N1—N2—H2	120 (2)	O1—C8—N2	122.8 (2)
O3—N3—O2	123.6 (3)	O1—C8—C9	120.5 (2)
O3—N3—C12	119.0 (3)	N2—C8—C9	116.7 (2)
O2—N3—C12	117.4 (3)	C10—C9—C14	119.4 (2)
C6—C1—C2	122.0 (3)	C10—C9—C8	122.8 (2)
C6—C1—Cl1	117.5 (2)	C14—C9—C8	117.8 (2)
C2—C1—Cl1	120.5 (2)	C9—C10—C11	120.3 (2)
C1—C2—C3	116.5 (2)	C9—C10—H10	119.8
C1—C2—C7	121.9 (2)	C11—C10—H10	119.8
C3—C2—C7	121.6 (2)	C12—C11—C10	118.5 (2)
C4—C3—C2	121.7 (3)	C12—C11—H11	120.7
C4—C3—H3	119.2	C10—C11—H11	120.7
C2—C3—H3	119.2	C13—C12—C11	122.4 (2)
C3—C4—C5	120.6 (3)	C13—C12—N3	119.2 (2)
C3—C4—H4	119.7	C11—C12—N3	118.4 (2)
C5—C4—H4	119.7	C12—C13—C14	118.5 (2)
C6—C5—C4	120.1 (3)	C12—C13—H13	120.7
C6—C5—H5	119.9	C14—C13—H13	120.7
C4—C5—H5	119.9	C13—C14—C9	120.7 (2)
C5—C6—C1	119.1 (3)	C13—C14—H14	119.6
C5—C6—H6	120.4	C9—C14—H14	119.6
C1—C6—H6	120.4

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.89 (1)	2.06 (1)	2.915 (3)	160 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.89 (1)	2.06 (1)	2.915 (3)	160 (3)

Symmetry code: (i) .