(E)-3-Bromo-N'-(4-hydr-oxy-3-nitro-benzyl-idene)benzohydrazide.

The title compound, C(14)H(10)BrN(3)O(4), was synthesized by the reaction of 4-hydr-oxy-3-nitro-benzaldehyde with an equimolar quantity of 3-bromo-benzohydrazide in methanol. The mol-ecule displays an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 4.6 (2)°. The nitro group is almost coplanar with the attached benzene ring [dihedral angle = 4.7 (2)°]. In the crystal structure, mol-ecules are linked into sheets parallel to (100) by inter-molecular N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds.

Related literature

For the crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009 ▶); Fun et al. (2008 ▶); Li & Ban (2009 ▶); Zhu et al. (2009 ▶); Yang (2007 ▶); You et al. (2008 ▶). For n class="Chemical">hydrazone compounds reported previously by our group, see: Qu et al. (2008 ▶); Yang et al. (2008 ▶); Cao & Lu (2009a ▶,b ▶).

Experimental

Crystal data

C14H10BrN3O4

M = 364.16

Monoclinic,

a = 12.323 (1) Å

b = 13.697 (1) Å

c = 8.430 (1) Å

β = 97.133 (2)°

V = 1411.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 2.93 mm−1

T = 298 K

0.23 × 0.21 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.552, T max = 0.592 (expected range = 0.519–0.556)

8326 measured reflections

2946 independent reflections

1834 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.128

S = 1.04

2946 reflections

203 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.66 e Å−3

Δρmin = −0.76 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/S1600536809024131/ci2834sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024131/ci2834Isup2.hkl

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

C14H10BrN3O4	F(000) = 728
Mr = 364.16	Dx = 1.713 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1828 reflections
a = 12.323 (1) Å	θ = 2.7–24.5°
b = 13.697 (1) Å	µ = 2.93 mm−1
c = 8.430 (1) Å	T = 298 K
β = 97.133 (2)°	Block, colourless
V = 1411.9 (2) Å3	0.23 × 0.21 × 0.20 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2946 independent reflections
Radiation source: fine-focus sealed tube	1834 reflections with I > 2σ(I)
graphite	Rint = 0.036
ω scans	θmax = 26.6°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→15
Tmin = 0.552, Tmax = 0.592	k = −16→17
8326 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0583P)2 + 0.7063P] where P = (Fo2 + 2Fc2)/3
2946 reflections	(Δ/σ)max = 0.001
203 parameters	Δρmax = 0.66 e Å−3
1 restraint	Δρmin = −0.76 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
Br1	1.07300 (4)	0.14793 (4)	0.14031 (6)	0.0779 (2)
N1	0.6951 (2)	0.3333 (2)	0.5669 (3)	0.0418 (7)
N2	0.7511 (2)	0.2683 (2)	0.4801 (3)	0.0402 (7)
N3	0.6518 (3)	0.7702 (2)	0.5895 (4)	0.0525 (8)
O1	0.7225 (3)	0.7781 (2)	0.5036 (4)	0.0735 (9)
O2	0.6110 (4)	0.8411 (2)	0.6463 (5)	0.0963 (13)
O3	0.4820 (2)	0.7296 (2)	0.7858 (4)	0.0660 (8)
H3	0.4390	0.7082	0.8440	0.099*
O4	0.7360 (3)	0.14917 (19)	0.6595 (3)	0.0731 (10)
C1	0.6432 (3)	0.4996 (2)	0.5965 (4)	0.0356 (8)
C2	0.6664 (3)	0.5944 (2)	0.5594 (4)	0.0366 (8)
H2A	0.7163	0.6068	0.4878	0.044*
C3	0.6159 (3)	0.6722 (3)	0.6279 (4)	0.0389 (8)
C4	0.5363 (3)	0.6554 (3)	0.7283 (4)	0.0444 (9)
C5	0.5151 (3)	0.5582 (3)	0.7673 (4)	0.0471 (9)
H5	0.4645	0.5452	0.8378	0.057*
C6	0.5678 (3)	0.4816 (3)	0.7031 (4)	0.0431 (9)
H6	0.5530	0.4177	0.7311	0.052*
C7	0.6986 (3)	0.4217 (2)	0.5201 (4)	0.0390 (8)
H7	0.7374	0.4368	0.4354	0.047*
C8	0.7693 (3)	0.1783 (3)	0.5364 (4)	0.0415 (9)
C9	0.8344 (3)	0.1142 (2)	0.4401 (4)	0.0373 (8)
C10	0.9097 (3)	0.1540 (3)	0.3480 (4)	0.0412 (9)
H10	0.9198	0.2212	0.3441	0.049*
C11	0.9692 (3)	0.0920 (3)	0.2625 (4)	0.0475 (9)
C12	0.9556 (3)	−0.0073 (3)	0.2673 (5)	0.0562 (11)
H12	0.9957	−0.0482	0.2084	0.067*
C13	0.8825 (3)	−0.0454 (3)	0.3592 (5)	0.0541 (11)
H13	0.8734	−0.1127	0.3633	0.065*
C14	0.8215 (3)	0.0146 (3)	0.4469 (4)	0.0442 (9)
H14	0.7723	−0.0123	0.5098	0.053*
H2	0.762 (4)	0.284 (3)	0.380 (2)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0654 (4)	0.0956 (4)	0.0811 (4)	0.0124 (3)	0.0426 (3)	−0.0031 (3)
N1	0.0517 (19)	0.0410 (18)	0.0368 (16)	0.0099 (14)	0.0213 (15)	0.0001 (13)
N2	0.0514 (18)	0.0363 (16)	0.0370 (17)	0.0089 (14)	0.0211 (15)	−0.0005 (13)
N3	0.063 (2)	0.0412 (19)	0.055 (2)	0.0061 (17)	0.0153 (18)	−0.0007 (15)
O1	0.079 (2)	0.0502 (18)	0.098 (2)	−0.0069 (15)	0.036 (2)	0.0067 (15)
O2	0.142 (3)	0.0425 (19)	0.117 (3)	0.0176 (19)	0.066 (3)	−0.0030 (17)
O3	0.0595 (19)	0.0610 (18)	0.084 (2)	0.0089 (14)	0.0343 (16)	−0.0240 (16)
O4	0.136 (3)	0.0419 (16)	0.0512 (18)	0.0135 (16)	0.0520 (19)	0.0077 (12)
C1	0.0356 (19)	0.0390 (19)	0.0329 (19)	0.0037 (15)	0.0067 (16)	−0.0029 (14)
C2	0.038 (2)	0.040 (2)	0.0325 (18)	0.0033 (16)	0.0098 (16)	0.0017 (15)
C3	0.040 (2)	0.039 (2)	0.039 (2)	0.0015 (15)	0.0091 (16)	−0.0020 (15)
C4	0.040 (2)	0.048 (2)	0.046 (2)	0.0051 (17)	0.0109 (18)	−0.0127 (17)
C5	0.046 (2)	0.053 (2)	0.046 (2)	−0.0032 (18)	0.0214 (18)	−0.0066 (17)
C6	0.047 (2)	0.041 (2)	0.044 (2)	−0.0028 (17)	0.0170 (18)	−0.0011 (16)
C7	0.044 (2)	0.042 (2)	0.0338 (19)	0.0043 (16)	0.0142 (16)	0.0030 (15)
C8	0.054 (2)	0.038 (2)	0.036 (2)	0.0040 (17)	0.0182 (18)	−0.0010 (15)
C9	0.043 (2)	0.0367 (19)	0.0326 (19)	0.0069 (15)	0.0054 (16)	−0.0014 (14)
C10	0.042 (2)	0.043 (2)	0.039 (2)	0.0085 (16)	0.0062 (17)	−0.0027 (16)
C11	0.044 (2)	0.055 (2)	0.045 (2)	0.0103 (18)	0.0102 (19)	−0.0068 (18)
C12	0.053 (3)	0.056 (3)	0.060 (3)	0.019 (2)	0.008 (2)	−0.021 (2)
C13	0.059 (3)	0.036 (2)	0.065 (3)	0.0088 (19)	−0.002 (2)	−0.0138 (18)
C14	0.046 (2)	0.042 (2)	0.044 (2)	0.0005 (17)	0.0044 (18)	−0.0029 (17)

Br1—C11	1.900 (4)	C4—C5	1.404 (5)
N1—C7	1.276 (4)	C5—C6	1.380 (5)
N1—N2	1.389 (4)	C5—H5	0.93
N2—C8	1.329 (4)	C6—H6	0.93
N2—H2	0.898 (10)	C7—H7	0.93
N3—O1	1.206 (4)	C8—C9	1.495 (5)
N3—O2	1.219 (4)	C9—C14	1.376 (5)
N3—C3	1.462 (5)	C9—C10	1.392 (5)
O3—C4	1.341 (4)	C10—C11	1.381 (5)
O3—H3	0.82	C10—H10	0.93
O4—C8	1.229 (4)	C11—C12	1.373 (6)
C1—C2	1.374 (5)	C12—C13	1.362 (6)
C1—C6	1.393 (5)	C12—H12	0.93
C1—C7	1.459 (5)	C13—C14	1.388 (5)
C2—C3	1.394 (5)	C13—H13	0.93
C2—H2A	0.93	C14—H14	0.93
C3—C4	1.392 (5)
C7—N1—N2	114.0 (3)	C1—C6—H6	119.9
C8—N2—N1	118.6 (3)	N1—C7—C1	121.5 (3)
C8—N2—H2	121 (3)	N1—C7—H7	119.3
N1—N2—H2	119 (3)	C1—C7—H7	119.3
O1—N3—O2	121.9 (4)	O4—C8—N2	122.9 (3)
O1—N3—C3	118.5 (3)	O4—C8—C9	121.7 (3)
O2—N3—C3	119.6 (3)	N2—C8—C9	115.4 (3)
C4—O3—H3	109.5	C14—C9—C10	120.0 (3)
C2—C1—C6	119.2 (3)	C14—C9—C8	119.2 (3)
C2—C1—C7	118.0 (3)	C10—C9—C8	120.9 (3)
C6—C1—C7	122.8 (3)	C11—C10—C9	119.0 (3)
C1—C2—C3	120.8 (3)	C11—C10—H10	120.5
C1—C2—H2A	119.6	C9—C10—H10	120.5
C3—C2—H2A	119.6	C12—C11—C10	121.3 (4)
C4—C3—C2	120.7 (3)	C12—C11—Br1	120.5 (3)
C4—C3—N3	122.8 (3)	C10—C11—Br1	118.2 (3)
C2—C3—N3	116.6 (3)	C13—C12—C11	119.2 (4)
O3—C4—C3	121.1 (3)	C13—C12—H12	120.4
O3—C4—C5	121.2 (3)	C11—C12—H12	120.4
C3—C4—C5	117.7 (3)	C12—C13—C14	121.0 (4)
C6—C5—C4	121.3 (3)	C12—C13—H13	119.5
C6—C5—H5	119.4	C14—C13—H13	119.5
C4—C5—H5	119.4	C9—C14—C13	119.5 (4)
C5—C6—C1	120.2 (3)	C9—C14—H14	120.2
C5—C6—H6	119.9	C13—C14—H14	120.2

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4i	0.90 (1)	2.06 (2)	2.914 (4)	159 (4)
O3—H3···N1ii	0.82	2.56	2.999 (4)	115
O3—H3···O4ii	0.82	2.30	2.992 (4)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4i	0.90 (1)	2.06 (2)	2.914 (4)	159 (4)
O3—H3⋯N1ii	0.82	2.56	2.999 (4)	115
O3—H3⋯O4ii	0.82	2.30	2.992 (4)	142

Symmetry codes: (i) ; (ii) .