(E)-N'-(2-Chloro-5-nitro-benzyl-idene)-4-methoxy-benzohydrazide.

In the title compound, C(15)H(12)ClN(3)O(4), the benzohydrazide group is not planar and the mol-ecule exists in a trans configuration with respect to the methyl-idene unit. The dihedral angle between the two substituted benzene rings is 0.4 (3)°. In the crystal structure, mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds, forming chains parallel to the c axis.

Related literature

For the biological activity of hydrazones, see: Zhong et al. (2007 ▶); Raj et al. (2007 ▶); Jimenez-Pulido et al. (2008 ▶). For related structures, see: Yehye et al. (2008 ▶); Fun, Patil, Jebas et al. (2008 ▶); Yang et al. (2008 ▶); Ejsmont et al. (2008 ▶); Fun, Patil, Rao et al. (2008 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H12ClN3O4

M = 333.73

Monoclinic,

a = 11.724 (2) Å

b = 13.482 (3) Å

c = 9.4259 (19) Å

β = 97.199 (3)°

V = 1478.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 298 (2) K

0.20 × 0.20 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.946, T max = 0.953

4284 measured reflections

2735 independent reflections

2320 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.089

S = 1.04

2735 reflections

212 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 1079 Friedel pairs

Flack parameter: −0.01 (7)

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034107/rz2255sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034107/rz2255Isup2.hkl

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

C15H12ClN3O4	F(000) = 688
Mr = 333.73	Dx = 1.500 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1899 reflections
a = 11.724 (2) Å	θ = 2.7–26.0°
b = 13.482 (3) Å	µ = 0.28 mm−1
c = 9.4259 (19) Å	T = 298 K
β = 97.199 (3)°	Block, colourless
V = 1478.1 (5) Å3	0.20 × 0.20 × 0.17 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2735 independent reflections
Radiation source: fine-focus sealed tube	2320 reflections with I > 2σ(I)
graphite	Rint = 0.015
ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→15
Tmin = 0.946, Tmax = 0.953	k = −17→14
4284 measured reflections	l = −12→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0432P)2 + 0.2836P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2735 reflections	Δρmax = 0.14 e Å−3
212 parameters	Δρmin = −0.19 e Å−3
3 restraints	Absolute structure: Flack (1983), 1079 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.01 (7)

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	0.12621 (9)	0.12406 (5)	0.37773 (10)	0.0861 (3)
N1	0.13488 (17)	0.41377 (14)	0.18463 (19)	0.0474 (5)
N2	0.09570 (18)	0.49328 (13)	0.2558 (2)	0.0477 (4)
N3	0.3330 (2)	0.2029 (2)	−0.1503 (3)	0.0806 (8)
O1	0.07475 (18)	0.58146 (13)	0.05053 (18)	0.0603 (5)
O2	−0.0721 (2)	0.92744 (16)	0.4294 (3)	0.0838 (7)
O3	0.3489 (3)	0.2876 (2)	−0.1823 (3)	0.1312 (12)
O4	0.3571 (2)	0.1320 (2)	−0.2230 (3)	0.1006 (8)
C1	0.1933 (2)	0.24746 (17)	0.1773 (2)	0.0466 (5)
C2	0.1870 (2)	0.15042 (18)	0.2246 (3)	0.0521 (6)
C3	0.2269 (2)	0.07102 (18)	0.1509 (3)	0.0625 (7)
H3	0.2211	0.0067	0.1848	0.075*
C4	0.2750 (2)	0.0880 (2)	0.0280 (3)	0.0626 (7)
H4	0.3019	0.0356	−0.0227	0.075*
C5	0.2829 (2)	0.1836 (2)	−0.0190 (3)	0.0574 (7)
C6	0.2439 (2)	0.26332 (17)	0.0522 (3)	0.0506 (6)
H6	0.2511	0.3273	0.0176	0.061*
C7	0.1489 (2)	0.33260 (16)	0.2508 (2)	0.0478 (5)
H7	0.1315	0.3267	0.3440	0.057*
C8	0.06846 (19)	0.57703 (16)	0.1789 (2)	0.0437 (5)
C9	0.0312 (2)	0.66442 (16)	0.2574 (2)	0.0432 (5)
C10	−0.0184 (2)	0.66089 (17)	0.3825 (2)	0.0466 (5)
H10	−0.0277	0.6001	0.4262	0.056*
C11	−0.0548 (2)	0.7478 (2)	0.4443 (3)	0.0536 (6)
H11	−0.0890	0.7449	0.5280	0.064*
C12	−0.0394 (2)	0.83779 (18)	0.3803 (3)	0.0594 (7)
C13	0.0120 (3)	0.8419 (2)	0.2577 (3)	0.0664 (7)
H13	0.0243	0.9031	0.2166	0.080*
C14	0.0454 (2)	0.75687 (18)	0.1949 (3)	0.0576 (7)
H14	0.0778	0.7607	0.1099	0.069*
C15	−0.1293 (3)	0.9299 (3)	0.5519 (5)	0.0924 (11)
H15A	−0.1978	0.8904	0.5359	0.139*
H15B	−0.1493	0.9972	0.5714	0.139*
H15C	−0.0796	0.9039	0.6320	0.139*
H2	0.085 (2)	0.490 (2)	0.3482 (13)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.1402 (7)	0.0565 (4)	0.0680 (4)	0.0130 (5)	0.0377 (4)	0.0108 (4)
N1	0.0625 (12)	0.0416 (10)	0.0391 (10)	0.0010 (8)	0.0102 (9)	−0.0058 (8)
N2	0.0704 (12)	0.0389 (9)	0.0353 (9)	0.0033 (8)	0.0128 (9)	−0.0020 (7)
N3	0.0738 (16)	0.094 (2)	0.0798 (18)	−0.0181 (14)	0.0314 (13)	−0.0263 (16)
O1	0.0928 (13)	0.0558 (9)	0.0343 (9)	0.0018 (9)	0.0157 (8)	0.0020 (7)
O2	0.0947 (15)	0.0526 (12)	0.1063 (18)	0.0148 (10)	0.0216 (13)	−0.0121 (11)
O3	0.187 (3)	0.098 (2)	0.131 (2)	−0.042 (2)	0.109 (2)	−0.0274 (17)
O4	0.1071 (17)	0.1107 (19)	0.0928 (16)	−0.0112 (14)	0.0478 (14)	−0.0467 (14)
C1	0.0483 (12)	0.0468 (12)	0.0440 (13)	−0.0013 (10)	0.0028 (10)	−0.0074 (10)
C2	0.0607 (15)	0.0487 (12)	0.0455 (13)	0.0046 (11)	0.0015 (11)	−0.0052 (10)
C3	0.0749 (17)	0.0441 (13)	0.0663 (18)	0.0083 (12)	0.0008 (14)	−0.0078 (12)
C4	0.0590 (15)	0.0581 (15)	0.0696 (18)	0.0076 (12)	0.0029 (13)	−0.0235 (13)
C5	0.0464 (14)	0.0688 (17)	0.0574 (15)	−0.0061 (11)	0.0080 (12)	−0.0217 (13)
C6	0.0500 (13)	0.0504 (13)	0.0517 (14)	−0.0037 (12)	0.0071 (11)	−0.0082 (11)
C7	0.0631 (14)	0.0425 (12)	0.0379 (12)	−0.0009 (11)	0.0067 (10)	−0.0031 (9)
C8	0.0553 (13)	0.0426 (11)	0.0339 (11)	−0.0066 (10)	0.0085 (9)	0.0000 (9)
C9	0.0510 (13)	0.0428 (11)	0.0352 (11)	0.0004 (10)	0.0028 (10)	−0.0001 (9)
C10	0.0563 (14)	0.0431 (12)	0.0399 (12)	−0.0016 (10)	0.0046 (11)	0.0018 (10)
C11	0.0512 (13)	0.0615 (16)	0.0481 (15)	0.0030 (12)	0.0064 (12)	−0.0111 (11)
C12	0.0589 (15)	0.0406 (13)	0.0752 (19)	0.0073 (11)	−0.0051 (14)	−0.0043 (12)
C13	0.0841 (19)	0.0430 (13)	0.0721 (18)	0.0036 (13)	0.0099 (15)	0.0094 (13)
C14	0.0753 (17)	0.0485 (14)	0.0507 (14)	−0.0021 (12)	0.0144 (13)	0.0100 (11)
C15	0.077 (2)	0.081 (2)	0.121 (3)	0.0114 (16)	0.017 (2)	−0.038 (2)

Cl1—C2	1.725 (3)	C4—H4	0.9300
N1—C7	1.260 (3)	C5—C6	1.376 (3)
N1—N2	1.374 (2)	C6—H6	0.9300
N2—C8	1.358 (3)	C7—H7	0.9300
N2—H2	0.897 (10)	C8—C9	1.485 (3)
N3—O3	1.202 (4)	C9—C10	1.379 (3)
N3—O4	1.229 (3)	C9—C14	1.397 (3)
N3—C5	1.458 (4)	C10—C11	1.399 (3)
O1—C8	1.223 (3)	C10—H10	0.9300
O2—C12	1.366 (3)	C11—C12	1.376 (4)
O2—C15	1.406 (4)	C11—H11	0.9300
C1—C2	1.387 (3)	C12—C13	1.370 (4)
C1—C6	1.402 (3)	C13—C14	1.370 (4)
C1—C7	1.469 (3)	C13—H13	0.9300
C2—C3	1.389 (3)	C14—H14	0.9300
C3—C4	1.370 (4)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.369 (4)	C15—H15C	0.9600
C7—N1—N2	117.83 (18)	C1—C7—H7	120.8
C8—N2—N1	117.34 (17)	O1—C8—N2	121.9 (2)
C8—N2—H2	120.9 (19)	O1—C8—C9	120.8 (2)
N1—N2—H2	121.7 (19)	N2—C8—C9	117.29 (18)
O3—N3—O4	123.0 (3)	C10—C9—C14	118.4 (2)
O3—N3—C5	118.3 (3)	C10—C9—C8	125.4 (2)
O4—N3—C5	118.7 (3)	C14—C9—C8	116.1 (2)
C12—O2—C15	118.8 (3)	C9—C10—C11	120.7 (2)
C2—C1—C6	117.3 (2)	C9—C10—H10	119.7
C2—C1—C7	123.4 (2)	C11—C10—H10	119.7
C6—C1—C7	119.3 (2)	C12—C11—C10	119.5 (2)
C1—C2—C3	122.1 (3)	C12—C11—H11	120.3
C1—C2—Cl1	120.45 (19)	C10—C11—H11	120.3
C3—C2—Cl1	117.4 (2)	O2—C12—C13	114.9 (3)
C4—C3—C2	119.6 (3)	O2—C12—C11	125.0 (3)
C4—C3—H3	120.2	C13—C12—C11	120.1 (2)
C2—C3—H3	120.2	C14—C13—C12	120.7 (2)
C5—C4—C3	118.9 (2)	C14—C13—H13	119.7
C5—C4—H4	120.6	C12—C13—H13	119.7
C3—C4—H4	120.6	C13—C14—C9	120.6 (2)
C4—C5—C6	122.5 (3)	C13—C14—H14	119.7
C4—C5—N3	119.5 (2)	C9—C14—H14	119.7
C6—C5—N3	118.0 (3)	O2—C15—H15A	109.5
C5—C6—C1	119.6 (2)	O2—C15—H15B	109.5
C5—C6—H6	120.2	H15A—C15—H15B	109.5
C1—C6—H6	120.2	O2—C15—H15C	109.5
N1—C7—C1	118.5 (2)	H15A—C15—H15C	109.5
N1—C7—H7	120.8	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.90 (1)	2.15 (2)	2.994 (3)	156 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.897 (10)	2.150 (15)	2.994 (3)	156 (3)

Symmetry code: (i) .