(E)-3-Bromo-N'-(5-bromo-2-hydroxy-benzyl-idene)benzohydrazide.

The title compound, C(14)H(10)Br(2)N(2)O(2), was synthesized by the reaction of 5-bromo-salicylaldehyde with an equimolar quantity of 3-bromo-benzohydrazide in methanol. The dihedral angle between the two benzene rings is 10.5 (4)°. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds to form chains parallel to the c axis, and an intra-molecular O-H⋯N inter-action also occurs.

Related literature

For related structures, see: Cao (2007a ▶,b ▶); Yang et al. (2008 ▶); Zhen & Han (2005 ▶); Peng & Hou (2008 ▶); Tang (2008 ▶); Salhin et al. (2007 ▶); Yathirajan et al. (2007 ▶).

Experimental

Crystal data

C14H10Br2N2O2

M = 398.06

Monoclinic,

a = 5.657 (5) Å

b = 32.08 (3) Å

c = 7.856 (7) Å

β = 93.217 (13)°

V = 1423 (2) Å3

Z = 4

Mo Kα radiation

μ = 5.70 mm−1

T = 298 (2) K

0.13 × 0.08 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.525, T max = 0.691

8526 measured reflections

3227 independent reflections

1830 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.108

S = 1.06

3227 reflections

185 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.63 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/S1600536808030675/bx2182sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030675/bx2182Isup2.hkl

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

C14H10Br2N2O2	F(000) = 776
Mr = 398.06	Dx = 1.858 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.657 (5) Å	Cell parameters from 1979 reflections
b = 32.08 (3) Å	θ = 2.5–25.3°
c = 7.856 (7) Å	µ = 5.70 mm−1
β = 93.217 (13)°	T = 298 K
V = 1423 (2) Å3	Block, colorless
Z = 4	0.13 × 0.08 × 0.07 mm

Bruker SMART CCD area-detector diffractometer	3227 independent reflections
Radiation source: fine-focus sealed tube	1830 reflections with I > 2σ(I)
graphite	Rint = 0.044
ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→5
Tmin = 0.525, Tmax = 0.691	k = −40→40
8526 measured reflections	l = −10→8

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) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0261P)2 + 2.1967P] where P = (Fo2 + 2Fc2)/3
3227 reflections	(Δ/σ)max = 0.001
185 parameters	Δρmax = 0.36 e Å−3
1 restraint	Δρmin = −0.62 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	0.52024 (14)	0.488709 (18)	0.25097 (9)	0.0871 (3)
Br2	0.48529 (11)	0.059801 (15)	0.43970 (8)	0.0683 (2)
O1	0.9846 (6)	0.33095 (11)	0.5203 (5)	0.0569 (9)
H1	0.8927	0.3112	0.5117	0.085*
O2	0.6434 (6)	0.22201 (10)	0.6015 (4)	0.0607 (10)
N1	0.5896 (7)	0.29247 (11)	0.4185 (5)	0.0451 (9)
N2	0.4480 (7)	0.25766 (12)	0.3888 (5)	0.0482 (10)
C1	0.6522 (8)	0.36456 (14)	0.3700 (5)	0.0398 (10)
C2	0.8762 (8)	0.36571 (15)	0.4560 (6)	0.0455 (11)
C3	0.9919 (10)	0.40362 (17)	0.4777 (7)	0.0596 (14)
H3	1.1409	0.4045	0.5339	0.072*
C4	0.8888 (11)	0.43984 (17)	0.4170 (7)	0.0655 (15)
H4	0.9687	0.4650	0.4317	0.079*
C5	0.6659 (10)	0.43900 (15)	0.3338 (6)	0.0572 (13)
C6	0.5510 (9)	0.40199 (14)	0.3089 (6)	0.0485 (12)
H6	0.4034	0.4015	0.2505	0.058*
C7	0.5168 (8)	0.32626 (14)	0.3474 (6)	0.0437 (11)
H7	0.3758	0.3264	0.2806	0.052*
C8	0.4901 (8)	0.22345 (14)	0.4857 (6)	0.0431 (11)
C9	0.3421 (8)	0.18595 (14)	0.4356 (5)	0.0398 (10)
C10	0.4437 (8)	0.14749 (13)	0.4676 (5)	0.0419 (11)
H10	0.5908	0.1456	0.5261	0.050*
C11	0.3267 (9)	0.11187 (14)	0.4127 (6)	0.0472 (12)
C12	0.1049 (9)	0.11408 (17)	0.3310 (6)	0.0568 (14)
H12	0.0270	0.0899	0.2939	0.068*
C13	0.0001 (9)	0.15246 (17)	0.3051 (6)	0.0547 (13)
H13	−0.1513	0.1542	0.2530	0.066*
C14	0.1181 (8)	0.18839 (15)	0.3557 (6)	0.0471 (12)
H14	0.0472	0.2142	0.3362	0.057*
H2	0.339 (7)	0.2580 (16)	0.301 (5)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.1139 (6)	0.0458 (3)	0.1014 (5)	0.0013 (3)	0.0025 (4)	0.0130 (3)
Br2	0.0836 (4)	0.0420 (3)	0.0786 (4)	−0.0039 (3)	−0.0013 (3)	0.0049 (3)
O1	0.038 (2)	0.064 (2)	0.067 (2)	−0.0044 (17)	−0.0141 (17)	0.0082 (19)
O2	0.068 (2)	0.0479 (19)	0.062 (2)	0.0009 (17)	−0.0422 (19)	0.0007 (16)
N1	0.049 (2)	0.039 (2)	0.045 (2)	−0.0038 (18)	−0.0151 (18)	−0.0009 (17)
N2	0.051 (3)	0.040 (2)	0.051 (2)	−0.0048 (19)	−0.027 (2)	0.0026 (18)
C1	0.034 (3)	0.050 (3)	0.035 (2)	−0.002 (2)	0.002 (2)	−0.006 (2)
C2	0.040 (3)	0.052 (3)	0.044 (3)	−0.007 (2)	0.001 (2)	−0.001 (2)
C3	0.050 (3)	0.069 (4)	0.058 (3)	−0.013 (3)	−0.007 (3)	−0.010 (3)
C4	0.073 (4)	0.057 (3)	0.065 (4)	−0.027 (3)	0.001 (3)	−0.006 (3)
C5	0.070 (4)	0.047 (3)	0.055 (3)	−0.007 (3)	0.006 (3)	0.002 (2)
C6	0.060 (3)	0.046 (3)	0.039 (3)	−0.002 (2)	−0.002 (2)	−0.001 (2)
C7	0.039 (3)	0.052 (3)	0.039 (3)	−0.003 (2)	−0.009 (2)	−0.002 (2)
C8	0.043 (3)	0.043 (3)	0.042 (3)	0.004 (2)	−0.011 (2)	−0.001 (2)
C9	0.042 (3)	0.049 (3)	0.027 (2)	−0.002 (2)	−0.009 (2)	0.0001 (19)
C10	0.039 (3)	0.049 (3)	0.037 (3)	0.000 (2)	−0.007 (2)	0.001 (2)
C11	0.057 (3)	0.046 (3)	0.039 (3)	−0.005 (2)	0.003 (2)	−0.001 (2)
C12	0.053 (3)	0.061 (3)	0.056 (3)	−0.022 (3)	−0.002 (3)	−0.002 (3)
C13	0.039 (3)	0.072 (4)	0.052 (3)	−0.011 (3)	−0.008 (2)	−0.004 (3)
C14	0.038 (3)	0.059 (3)	0.043 (3)	0.000 (2)	−0.001 (2)	0.001 (2)

Br1—C5	1.893 (5)	C4—H4	0.9300
Br2—C11	1.902 (5)	C5—C6	1.362 (6)
O1—C2	1.356 (5)	C6—H6	0.9300
O1—H1	0.8200	C7—H7	0.9300
O2—C8	1.222 (5)	C8—C9	1.505 (6)
N1—C7	1.277 (5)	C9—C10	1.378 (6)
N1—N2	1.386 (5)	C9—C14	1.385 (6)
N2—C8	1.349 (6)	C10—C11	1.377 (6)
N2—H2	0.90 (4)	C10—H10	0.9300
C1—C2	1.402 (6)	C11—C12	1.379 (7)
C1—C6	1.403 (6)	C12—C13	1.376 (7)
C1—C7	1.453 (6)	C12—H12	0.9300
C2—C3	1.387 (6)	C13—C14	1.379 (6)
C3—C4	1.373 (7)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.387 (7)
C2—O1—H1	109.5	N1—C7—H7	119.7
C7—N1—N2	116.2 (4)	C1—C7—H7	119.7
C8—N2—N1	118.6 (3)	O2—C8—N2	123.1 (4)
C8—N2—H2	122 (4)	O2—C8—C9	121.7 (4)
N1—N2—H2	119 (4)	N2—C8—C9	115.1 (4)
C2—C1—C6	118.9 (4)	C10—C9—C14	119.7 (4)
C2—C1—C7	122.5 (4)	C10—C9—C8	116.6 (4)
C6—C1—C7	118.6 (4)	C14—C9—C8	123.7 (4)
O1—C2—C3	118.3 (4)	C11—C10—C9	119.8 (4)
O1—C2—C1	122.3 (4)	C11—C10—H10	120.1
C3—C2—C1	119.3 (5)	C9—C10—H10	120.1
C4—C3—C2	120.7 (5)	C10—C11—C12	120.8 (5)
C4—C3—H3	119.6	C10—C11—Br2	118.6 (4)
C2—C3—H3	119.6	C12—C11—Br2	120.6 (4)
C3—C4—C5	120.3 (5)	C13—C12—C11	119.2 (5)
C3—C4—H4	119.9	C13—C12—H12	120.4
C5—C4—H4	119.9	C11—C12—H12	120.4
C6—C5—C4	119.9 (5)	C12—C13—C14	120.5 (5)
C6—C5—Br1	119.3 (4)	C12—C13—H13	119.8
C4—C5—Br1	120.8 (4)	C14—C13—H13	119.8
C5—C6—C1	120.9 (5)	C13—C14—C9	119.9 (5)
C5—C6—H6	119.5	C13—C14—H14	120.0
C1—C6—H6	119.5	C9—C14—H14	120.0
N1—C7—C1	120.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.92	2.638 (5)	145
N2—H2···O2i	0.90 (4)	1.98 (2)	2.838 (5)	160 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.92	2.638 (5)	145
N2—H2⋯O2i	0.90 (4)	1.98 (2)	2.838 (5)	160 (5)

Symmetry code: (i) .