3-Chloro-N'-(2-chloro-5-nitro-benzyl-idene)-benzohydrazide.

The title mol-ecule, C(14)H(9)Cl(2)N(3)O(3), has an E configuration with respect to the methyl-idene unit. The dihedral angle between the mean planes of the two benzene rings is 12.3 (3)°. In the crystal, mol-ecules are linked via bifurcated N-H⋯(O, N) hydrogen bonds into chains along [001].

Related literature

For the biological applications of hydrazone compounds, see: Ajani et al. (2010 ▶); Avaji et al. (2009 ▶); Fan et al. (2010 ▶); Rasras et al. (2010 ▶). For related hydrazone structures, see: Zhang (2011a ▶,b ▶); Ahmad et al. (2010 ▶); Ban (2010 ▶); Ji & Lu (2010 ▶); Shalash et al. (2010 ▶).

Experimental

Crystal data

C14H9Cl2N3O3

M = 338.14

Monoclinic,

a = 7.770 (2) Å

b = 24.254 (6) Å

c = 7.889 (2) Å

β = 95.383 (3)°

V = 1480.1 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.45 mm−1

T = 298 K

0.32 × 0.30 × 0.30 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.868, T max = 0.876

7538 measured reflections

3016 independent reflections

1607 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.152

S = 1.04

3016 reflections

202 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 datablock(s) global, I. DOI: 10.1107/S160053681102157X/lh5264sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102157X/lh5264Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681102157X/lh5264Isup3.cml

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

C14H9Cl2N3O3	F(000) = 688
Mr = 338.14	Dx = 1.517 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 814 reflections
a = 7.770 (2) Å	θ = 2.6–24.5°
b = 24.254 (6) Å	µ = 0.45 mm−1
c = 7.889 (2) Å	T = 298 K
β = 95.383 (3)°	Block, yellow
V = 1480.1 (7) Å3	0.32 × 0.30 × 0.30 mm
Z = 4

Bruker SMART APEX CCD diffractometer	3016 independent reflections
Radiation source: fine-focus sealed tube	1607 reflections with I > 2σ(I)
graphite	Rint = 0.055
ω scans	θmax = 26.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −5→9
Tmin = 0.868, Tmax = 0.876	k = −30→30
7538 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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0443P)2 + 0.2711P] where P = (Fo2 + 2Fc2)/3
3016 reflections	(Δ/σ)max < 0.001
202 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.33815 (15)	0.55819 (4)	0.48098 (13)	0.0786 (4)
Cl2	0.02262 (16)	0.99758 (4)	0.26818 (14)	0.0827 (4)
N1	0.2837 (3)	0.72544 (12)	0.6153 (3)	0.0429 (7)
N2	0.1950 (4)	0.75727 (12)	0.4918 (3)	0.0459 (7)
N3	0.6550 (5)	0.65111 (19)	1.1284 (4)	0.0771 (11)
O1	0.7009 (5)	0.61872 (16)	1.2395 (4)	0.1306 (15)
O2	0.6670 (5)	0.70061 (16)	1.1441 (4)	0.1060 (12)
O3	0.1450 (4)	0.82247 (10)	0.6847 (3)	0.0701 (8)
C1	0.4302 (4)	0.64304 (14)	0.6916 (4)	0.0425 (8)
C2	0.4361 (4)	0.58649 (14)	0.6668 (4)	0.0493 (9)
C3	0.5135 (5)	0.55147 (15)	0.7884 (5)	0.0591 (10)
H3	0.5166	0.5137	0.7681	0.071*
C4	0.5859 (5)	0.57270 (16)	0.9396 (5)	0.0602 (10)
H4	0.6375	0.5495	1.0235	0.072*
C5	0.5812 (4)	0.62850 (16)	0.9653 (4)	0.0513 (9)
C6	0.5069 (4)	0.66400 (14)	0.8457 (4)	0.0464 (9)
H6	0.5073	0.7017	0.8665	0.056*
C7	0.3405 (4)	0.67978 (15)	0.5662 (4)	0.0469 (9)
H7	0.3252	0.6698	0.4519	0.056*
C8	0.1301 (5)	0.80617 (14)	0.5386 (4)	0.0467 (9)
C9	0.0426 (4)	0.83855 (13)	0.3958 (4)	0.0427 (8)
C10	0.0624 (4)	0.89538 (14)	0.4003 (4)	0.0475 (9)
H10	0.1224	0.9123	0.4938	0.057*
C11	−0.0076 (5)	0.92655 (15)	0.2651 (4)	0.0520 (9)
C12	−0.1003 (5)	0.90243 (17)	0.1273 (5)	0.0587 (10)
H12	−0.1459	0.9239	0.0362	0.070*
C13	−0.1246 (5)	0.84646 (16)	0.1259 (4)	0.0574 (10)
H13	−0.1891	0.8300	0.0342	0.069*
C14	−0.0544 (4)	0.81411 (15)	0.2593 (4)	0.0472 (9)
H14	−0.0720	0.7762	0.2576	0.057*
H2	0.193 (4)	0.7439 (12)	0.386 (2)	0.057*

	U11	U22	U33	U12	U13	U23
Cl1	0.0933 (9)	0.0746 (7)	0.0636 (7)	0.0081 (6)	−0.0147 (6)	−0.0264 (6)
Cl2	0.1195 (10)	0.0564 (7)	0.0692 (7)	0.0114 (6)	−0.0070 (7)	0.0126 (5)
N1	0.0476 (17)	0.0491 (17)	0.0306 (15)	0.0043 (14)	−0.0040 (13)	0.0048 (13)
N2	0.0595 (19)	0.0541 (19)	0.0229 (14)	0.0092 (15)	−0.0032 (13)	0.0008 (13)
N3	0.084 (3)	0.092 (3)	0.050 (2)	0.005 (2)	−0.0218 (19)	0.002 (2)
O1	0.195 (4)	0.126 (3)	0.058 (2)	0.012 (3)	−0.058 (2)	0.018 (2)
O2	0.134 (3)	0.094 (3)	0.080 (2)	0.007 (2)	−0.044 (2)	−0.024 (2)
O3	0.114 (2)	0.0647 (17)	0.0285 (13)	0.0229 (16)	−0.0129 (14)	−0.0066 (12)
C1	0.041 (2)	0.051 (2)	0.0342 (18)	0.0037 (16)	−0.0001 (15)	−0.0010 (15)
C2	0.051 (2)	0.054 (2)	0.041 (2)	0.0050 (18)	−0.0016 (17)	−0.0074 (17)
C3	0.070 (3)	0.047 (2)	0.060 (3)	0.0069 (19)	0.001 (2)	0.0013 (18)
C4	0.066 (3)	0.061 (3)	0.052 (2)	0.008 (2)	−0.003 (2)	0.013 (2)
C5	0.048 (2)	0.064 (3)	0.039 (2)	0.0007 (18)	−0.0092 (17)	0.0020 (18)
C6	0.046 (2)	0.052 (2)	0.040 (2)	0.0069 (17)	−0.0018 (17)	−0.0033 (16)
C7	0.054 (2)	0.056 (2)	0.0293 (18)	0.0050 (19)	−0.0023 (16)	−0.0036 (16)
C8	0.056 (2)	0.049 (2)	0.034 (2)	0.0029 (18)	−0.0014 (17)	0.0023 (16)
C9	0.047 (2)	0.052 (2)	0.0289 (18)	0.0104 (17)	−0.0008 (15)	0.0027 (15)
C10	0.058 (2)	0.054 (2)	0.0304 (19)	0.0052 (18)	−0.0012 (16)	−0.0006 (16)
C11	0.060 (2)	0.055 (2)	0.040 (2)	0.0103 (19)	0.0020 (18)	0.0079 (17)
C12	0.060 (3)	0.074 (3)	0.040 (2)	0.018 (2)	−0.0058 (19)	0.0102 (19)
C13	0.061 (2)	0.074 (3)	0.034 (2)	0.010 (2)	−0.0105 (18)	−0.0010 (19)
C14	0.049 (2)	0.055 (2)	0.0365 (19)	0.0067 (17)	0.0002 (17)	−0.0011 (16)

Cl1—C2	1.729 (3)	C4—C5	1.370 (5)
Cl2—C11	1.738 (4)	C4—H4	0.9300
N1—C7	1.266 (4)	C5—C6	1.365 (4)
N1—N2	1.376 (3)	C6—H6	0.9300
N2—C8	1.354 (4)	C7—H7	0.9300
N2—H2	0.893 (10)	C8—C9	1.485 (4)
N3—O1	1.206 (4)	C9—C10	1.387 (4)
N3—O2	1.210 (4)	C9—C14	1.388 (4)
N3—C5	1.465 (5)	C10—C11	1.377 (4)
O3—C8	1.214 (4)	C10—H10	0.9300
C1—C2	1.387 (5)	C11—C12	1.377 (5)
C1—C6	1.398 (4)	C12—C13	1.371 (5)
C1—C7	1.460 (4)	C12—H12	0.9300
C2—C3	1.377 (5)	C13—C14	1.383 (4)
C3—C4	1.371 (5)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C7—N1—N2	116.1 (3)	N1—C7—C1	119.0 (3)
C8—N2—N1	118.2 (3)	N1—C7—H7	120.5
C8—N2—H2	127 (2)	C1—C7—H7	120.5
N1—N2—H2	115 (2)	O3—C8—N2	122.7 (3)
O1—N3—O2	123.9 (4)	O3—C8—C9	123.0 (3)
O1—N3—C5	117.3 (4)	N2—C8—C9	114.3 (3)
O2—N3—C5	118.8 (3)	C10—C9—C14	119.7 (3)
C2—C1—C6	117.7 (3)	C10—C9—C8	117.7 (3)
C2—C1—C7	121.9 (3)	C14—C9—C8	122.6 (3)
C6—C1—C7	120.3 (3)	C11—C10—C9	119.4 (3)
C3—C2—C1	122.0 (3)	C11—C10—H10	120.3
C3—C2—Cl1	118.3 (3)	C9—C10—H10	120.3
C1—C2—Cl1	119.7 (3)	C12—C11—C10	121.2 (4)
C4—C3—C2	119.4 (3)	C12—C11—Cl2	119.5 (3)
C4—C3—H3	120.3	C10—C11—Cl2	119.4 (3)
C2—C3—H3	120.3	C13—C12—C11	119.3 (3)
C5—C4—C3	119.1 (3)	C13—C12—H12	120.4
C5—C4—H4	120.5	C11—C12—H12	120.4
C3—C4—H4	120.5	C12—C13—C14	120.8 (3)
C6—C5—C4	122.4 (3)	C12—C13—H13	119.6
C6—C5—N3	118.5 (4)	C14—C13—H13	119.6
C4—C5—N3	119.1 (3)	C13—C14—C9	119.7 (3)
C5—C6—C1	119.3 (3)	C13—C14—H14	120.2
C5—C6—H6	120.3	C9—C14—H14	120.2
C1—C6—H6	120.3

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1i	0.89 (1)	2.43 (2)	3.139 (4)	137 (3)
N2—H2···O3i	0.89 (1)	2.27 (2)	3.095 (4)	154 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1i	0.89 (1)	2.43 (2)	3.139 (4)	137 (3)
N2—H2⋯O3i	0.89 (1)	2.27 (2)	3.095 (4)	154 (3)

Symmetry code: (i) .