N'-(5-Bromo-2-hydroxy-benzyl-idene)-4-chloro-benzohydrazide.

The title Schiff base, C(14)H(10)BrClN(2)O(2), exists in a trans configuration with respect to the C=N bond and the dihedral angle between the two benzene rings is 0.8 (2)°. There is an intra-molecular O-H⋯N hydrogen bond in the mol-ecule, which generates an S(6) loop. In the crystal, inter-molecular N-H⋯O hydrogen bonds link adjacent mol-ecules into extended chains propagating along the c-axis direction.

Related literature

For background to the biological properties of Schiff bases, see: Ritter et al. (2009 ▶); Bagihalli et al. (2008 ▶). For related structures, see: Fun et al. (2008 ▶); Shafiq et al. (2009 ▶); Goh et al. (2010 ▶). Zhou et al. (2009 ▶); Zhou & Yang (2009 ▶, 2010a ▶,b ▶).

Experimental

Crystal data

C14H10BrClN2O2

M = 353.60

Monoclinic,

a = 5.893 (2) Å

b = 31.708 (11) Å

c = 7.437 (3) Å

β = 92.017 (8)°

V = 1388.8 (9) Å3

Z = 4

Mo Kα radiation

μ = 3.15 mm−1

T = 298 K

0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.616, T max = 0.649

7670 measured reflections

2661 independent reflections

1555 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.119

S = 1.02

2661 reflections

185 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.58 e Å−3

Δρmin = −0.51 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/S160053681000752X/hb5343sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000752X/hb5343Isup2.hkl

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

C14H10BrClN2O2	F(000) = 704
Mr = 353.60	Dx = 1.691 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1461 reflections
a = 5.893 (2) Å	θ = 2.5–24.5°
b = 31.708 (11) Å	µ = 3.15 mm−1
c = 7.437 (3) Å	T = 298 K
β = 92.017 (8)°	Block, colourless
V = 1388.8 (9) Å3	0.17 × 0.15 × 0.15 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	2661 independent reflections
Radiation source: fine-focus sealed tube	1555 reflections with I > 2σ(I)
graphite	Rint = 0.043
ω scans	θmax = 25.9°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.616, Tmax = 0.649	k = −38→36
7670 measured reflections	l = −9→5

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0584P)2] where P = (Fo2 + 2Fc2)/3
2661 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.58 e Å−3
1 restraint	Δρmin = −0.51 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	0.22343 (9)	0.007519 (14)	0.69748 (8)	0.0934 (3)
Cl1	−0.31634 (18)	0.42871 (3)	0.73651 (14)	0.0726 (4)
N1	0.3457 (5)	0.20659 (9)	0.8247 (3)	0.0456 (7)
N2	0.2126 (5)	0.24185 (9)	0.7948 (4)	0.0508 (8)
O1	0.7208 (4)	0.16526 (8)	0.9180 (4)	0.0621 (7)
H1	0.6422	0.1863	0.8999	0.093*
O2	0.4098 (4)	0.27888 (7)	1.0046 (3)	0.0604 (7)
C1	0.3853 (6)	0.13282 (10)	0.7884 (4)	0.0418 (8)
C2	0.6036 (6)	0.13063 (12)	0.8651 (4)	0.0479 (9)
C3	0.7070 (6)	0.09163 (14)	0.8872 (5)	0.0617 (11)
H3	0.8539	0.0902	0.9369	0.074*
C4	0.5988 (7)	0.05541 (13)	0.8381 (5)	0.0665 (11)
H4	0.6702	0.0295	0.8553	0.080*
C5	0.3815 (7)	0.05740 (11)	0.7622 (5)	0.0561 (10)
C6	0.2773 (6)	0.09556 (11)	0.7367 (4)	0.0485 (9)
H6	0.1320	0.0966	0.6840	0.058*
C7	0.2645 (6)	0.17218 (11)	0.7635 (4)	0.0446 (9)
H7	0.1247	0.1723	0.7015	0.054*
C8	0.2553 (6)	0.27691 (10)	0.8913 (5)	0.0430 (8)
C9	0.1038 (5)	0.31345 (10)	0.8524 (4)	0.0385 (8)
C10	−0.1114 (6)	0.30975 (11)	0.7758 (4)	0.0470 (9)
H10	−0.1700	0.2832	0.7491	0.056*
C11	−0.2404 (6)	0.34505 (12)	0.7387 (5)	0.0506 (9)
H11	−0.3850	0.3425	0.6856	0.061*
C12	−0.1537 (6)	0.38413 (11)	0.7806 (4)	0.0471 (9)
C13	0.0603 (6)	0.38863 (11)	0.8575 (4)	0.0511 (9)
H13	0.1184	0.4153	0.8838	0.061*
C14	0.1861 (6)	0.35333 (11)	0.8947 (4)	0.0465 (9)
H14	0.3297	0.3561	0.9495	0.056*
H2	0.107 (5)	0.2405 (12)	0.705 (4)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.1054 (5)	0.0446 (3)	0.1297 (5)	−0.0038 (2)	−0.0018 (3)	0.0039 (3)
Cl1	0.0765 (8)	0.0562 (7)	0.0844 (8)	0.0210 (5)	−0.0079 (6)	−0.0056 (5)
N1	0.0462 (18)	0.0458 (18)	0.0441 (17)	0.0073 (14)	−0.0094 (13)	−0.0009 (13)
N2	0.055 (2)	0.0462 (19)	0.050 (2)	0.0044 (15)	−0.0177 (14)	−0.0068 (15)
O1	0.0459 (15)	0.0723 (18)	0.0670 (18)	0.0040 (13)	−0.0124 (13)	−0.0054 (15)
O2	0.0676 (17)	0.0470 (15)	0.0639 (17)	−0.0021 (13)	−0.0335 (14)	0.0001 (12)
C1	0.043 (2)	0.046 (2)	0.037 (2)	0.0041 (16)	0.0006 (15)	0.0014 (15)
C2	0.046 (2)	0.057 (2)	0.040 (2)	0.0024 (18)	0.0003 (17)	−0.0009 (17)
C3	0.044 (2)	0.079 (3)	0.062 (3)	0.019 (2)	−0.0053 (18)	0.008 (2)
C4	0.068 (3)	0.060 (3)	0.071 (3)	0.024 (2)	0.003 (2)	0.008 (2)
C5	0.065 (3)	0.047 (2)	0.057 (2)	0.0047 (19)	0.006 (2)	0.0083 (17)
C6	0.048 (2)	0.045 (2)	0.052 (2)	0.0037 (16)	−0.0027 (17)	0.0042 (16)
C7	0.043 (2)	0.048 (2)	0.042 (2)	0.0044 (17)	−0.0053 (16)	0.0019 (16)
C8	0.041 (2)	0.043 (2)	0.045 (2)	−0.0061 (15)	−0.0073 (17)	0.0019 (16)
C9	0.042 (2)	0.0411 (19)	0.0325 (18)	−0.0023 (15)	−0.0044 (15)	−0.0008 (15)
C10	0.051 (2)	0.042 (2)	0.048 (2)	−0.0024 (16)	−0.0004 (17)	−0.0065 (16)
C11	0.048 (2)	0.053 (3)	0.051 (2)	0.0031 (18)	−0.0027 (17)	−0.0043 (17)
C12	0.056 (2)	0.045 (2)	0.041 (2)	0.0075 (17)	0.0085 (17)	−0.0042 (16)
C13	0.060 (3)	0.041 (2)	0.052 (2)	−0.0033 (18)	0.0023 (18)	−0.0062 (17)
C14	0.045 (2)	0.050 (2)	0.045 (2)	−0.0046 (17)	−0.0068 (16)	−0.0041 (16)

Br1—C5	1.889 (4)	C4—H4	0.9300
Cl1—C12	1.733 (4)	C5—C6	1.367 (5)
N1—C7	1.269 (4)	C6—H6	0.9300
N1—N2	1.379 (4)	C7—H7	0.9300
N2—C8	1.342 (4)	C8—C9	1.485 (4)
N2—H2	0.898 (10)	C9—C10	1.377 (4)
O1—C2	1.349 (4)	C9—C14	1.387 (4)
O1—H1	0.8200	C10—C11	1.376 (5)
O2—C8	1.220 (4)	C10—H10	0.9300
C1—C6	1.390 (5)	C11—C12	1.372 (5)
C1—C2	1.391 (5)	C11—H11	0.9300
C1—C7	1.445 (5)	C12—C13	1.373 (5)
C2—C3	1.386 (5)	C13—C14	1.366 (5)
C3—C4	1.358 (5)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.383 (5)
C7—N1—N2	115.7 (3)	N1—C7—H7	119.4
C8—N2—N1	119.4 (3)	C1—C7—H7	119.4
C8—N2—H2	123 (3)	O2—C8—N2	122.2 (3)
N1—N2—H2	117 (3)	O2—C8—C9	121.6 (3)
C2—O1—H1	109.5	N2—C8—C9	116.2 (3)
C6—C1—C2	118.6 (3)	C10—C9—C14	118.8 (3)
C6—C1—C7	118.7 (3)	C10—C9—C8	123.6 (3)
C2—C1—C7	122.7 (3)	C14—C9—C8	117.7 (3)
O1—C2—C3	118.3 (3)	C11—C10—C9	120.6 (3)
O1—C2—C1	122.4 (3)	C11—C10—H10	119.7
C3—C2—C1	119.3 (3)	C9—C10—H10	119.7
C4—C3—C2	121.5 (4)	C12—C11—C10	119.3 (3)
C4—C3—H3	119.2	C12—C11—H11	120.3
C2—C3—H3	119.2	C10—C11—H11	120.3
C3—C4—C5	119.4 (4)	C11—C12—C13	121.2 (3)
C3—C4—H4	120.3	C11—C12—Cl1	119.6 (3)
C5—C4—H4	120.3	C13—C12—Cl1	119.2 (3)
C6—C5—C4	120.1 (4)	C14—C13—C12	118.9 (3)
C6—C5—Br1	119.4 (3)	C14—C13—H13	120.5
C4—C5—Br1	120.5 (3)	C12—C13—H13	120.5
C5—C6—C1	121.0 (3)	C13—C14—C9	121.2 (3)
C5—C6—H6	119.5	C13—C14—H14	119.4
C1—C6—H6	119.5	C9—C14—H14	119.4
N1—C7—C1	121.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.93	2.642 (4)	145
N2—H2···O2i	0.90 (1)	1.96 (2)	2.829 (3)	163 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.93	2.642 (4)	145
N2—H2⋯O2i	0.90 (1)	1.96 (2)	2.829 (3)	163 (4)

Symmetry code: (i) .