3-Bromo-N'-(3,5-dichloro-2-hydroxy-benzyl-idene)benzohydrazide.

The title compound, C(14)H(9)BrCl(2)N(2)O(2), was prepared by the reaction of 3,5-dichloro-2-hydroxy-benzaldehyde and 3-bromo-benzohydrazide in methanol. The dihedral angle between the two benzene rings is 13.0 (2)°. An intra-molecular O-H⋯N hydrogen bond is observed. The mol-ecules are linked into chains along the c axis by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For the synthesis of Schiff bases, see: Akitsu & Einaga (2006 ▶); Butcher et al. (2005 ▶); Habibi et al. (2007 ▶); Pradeep (2005 ▶). For related structures, see: Bao & Wei (2008 ▶); Odabaşoğlu et al. (2007 ▶); Wang et al. (2006 ▶); Wei et al. (2008 ▶); Yathirajan et al. (2007 ▶); Yehye et al. (2008 ▶); Zhu et al. (2007 ▶).

Experimental

Crystal data

C14H9BrCl2N2O2

M = 388.04

Monoclinic,

a = 8.272 (2) Å

b = 22.366 (3) Å

c = 8.237 (2) Å

β = 104.014 (2)°

V = 1478.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 3.15 mm−1

T = 298 (2) K

0.23 × 0.23 × 0.22 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.495, T max = 0.513

8590 measured reflections

3224 independent reflections

2144 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.075

S = 0.98

3224 reflections

194 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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/S1600536808041378/ci2740sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041378/ci2740Isup2.hkl

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

C14H9BrCl2N2O2	F(000) = 768
Mr = 388.04	Dx = 1.743 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1779 reflections
a = 8.272 (2) Å	θ = 2.5–24.9°
b = 22.366 (3) Å	µ = 3.15 mm−1
c = 8.237 (2) Å	T = 298 K
β = 104.014 (2)°	Cut from needle, colorless
V = 1478.6 (5) Å3	0.23 × 0.23 × 0.22 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	3224 independent reflections
Radiation source: fine-focus sealed tube	2144 reflections with I > 2σ(I)
graphite	Rint = 0.035
ω scans	θmax = 27.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.495, Tmax = 0.513	k = −25→28
8590 measured reflections	l = −9→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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.0309P)2] where P = (Fo2 + 2Fc2)/3
3224 reflections	(Δ/σ)max = 0.001
194 parameters	Δρmax = 0.32 e Å−3
1 restraint	Δρmin = −0.29 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
Br1	0.48270 (4)	0.491887 (13)	−0.27385 (4)	0.05628 (13)
Cl1	1.05566 (10)	1.05415 (3)	0.26163 (9)	0.0498 (2)
Cl2	1.25693 (10)	0.85535 (3)	0.61875 (9)	0.0575 (2)
N1	0.7849 (3)	0.79256 (10)	0.0814 (3)	0.0410 (6)
N2	0.6808 (3)	0.76119 (10)	−0.0450 (3)	0.0422 (6)
O1	1.0195 (3)	0.79478 (8)	0.3556 (2)	0.0541 (5)
H1	0.9462	0.7793	0.2827	0.081*
O2	0.6767 (3)	0.68457 (8)	0.1345 (2)	0.0489 (5)
C1	0.9228 (3)	0.88201 (12)	0.1849 (3)	0.0367 (6)
C2	1.0236 (3)	0.85387 (12)	0.3269 (3)	0.0395 (7)
C3	1.1329 (3)	0.88909 (12)	0.4431 (3)	0.0397 (7)
C4	1.1435 (3)	0.94963 (12)	0.4228 (3)	0.0409 (7)
H4	1.2183	0.9722	0.5017	0.049*
C5	1.0430 (3)	0.97700 (11)	0.2850 (3)	0.0373 (7)
C6	0.9340 (3)	0.94382 (12)	0.1660 (3)	0.0387 (7)
H6	0.8676	0.9626	0.0726	0.046*
C7	0.8091 (3)	0.84757 (12)	0.0558 (3)	0.0417 (7)
H7	0.7548	0.8656	−0.0442	0.050*
C8	0.6373 (3)	0.70501 (12)	−0.0078 (3)	0.0392 (7)
C9	0.5343 (3)	0.67109 (12)	−0.1518 (3)	0.0373 (6)
C10	0.5519 (3)	0.60935 (11)	−0.1486 (3)	0.0371 (6)
H10	0.6248	0.5906	−0.0595	0.044*
C11	0.4591 (3)	0.57631 (12)	−0.2802 (3)	0.0404 (7)
C12	0.3488 (4)	0.60312 (13)	−0.4123 (3)	0.0468 (7)
H12	0.2877	0.5801	−0.5000	0.056*
C13	0.3297 (4)	0.66421 (13)	−0.4133 (4)	0.0500 (8)
H13	0.2544	0.6826	−0.5013	0.060*
C14	0.4222 (4)	0.69829 (13)	−0.2838 (3)	0.0444 (7)
H14	0.4093	0.7396	−0.2852	0.053*
H2	0.662 (4)	0.7733 (13)	−0.1513 (18)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0667 (2)	0.04067 (18)	0.0550 (2)	−0.00069 (16)	0.00200 (16)	−0.00918 (15)
Cl1	0.0677 (6)	0.0367 (4)	0.0459 (4)	−0.0006 (3)	0.0154 (4)	0.0005 (3)
Cl2	0.0656 (6)	0.0545 (5)	0.0430 (4)	0.0122 (4)	−0.0048 (4)	0.0070 (4)
N1	0.0484 (15)	0.0403 (14)	0.0325 (13)	−0.0066 (11)	0.0066 (11)	−0.0035 (11)
N2	0.0558 (16)	0.0401 (13)	0.0280 (12)	−0.0083 (12)	0.0053 (12)	−0.0038 (11)
O1	0.0718 (17)	0.0375 (11)	0.0463 (13)	−0.0037 (10)	0.0013 (11)	0.0071 (10)
O2	0.0714 (15)	0.0428 (11)	0.0283 (11)	−0.0042 (10)	0.0042 (10)	−0.0001 (9)
C1	0.0396 (16)	0.0403 (16)	0.0311 (14)	−0.0024 (13)	0.0103 (12)	−0.0019 (13)
C2	0.0462 (18)	0.0379 (16)	0.0361 (16)	0.0023 (13)	0.0130 (14)	0.0055 (13)
C3	0.0410 (17)	0.0448 (17)	0.0311 (15)	0.0044 (14)	0.0047 (13)	0.0022 (13)
C4	0.0429 (18)	0.0442 (17)	0.0335 (15)	−0.0037 (14)	0.0050 (13)	−0.0038 (13)
C5	0.0457 (19)	0.0329 (15)	0.0346 (15)	−0.0011 (12)	0.0119 (14)	−0.0007 (12)
C6	0.0467 (18)	0.0403 (16)	0.0295 (14)	0.0050 (14)	0.0100 (13)	0.0049 (13)
C7	0.0463 (19)	0.0455 (18)	0.0324 (15)	−0.0037 (14)	0.0076 (13)	−0.0004 (13)
C8	0.0462 (18)	0.0393 (16)	0.0317 (16)	0.0023 (13)	0.0085 (13)	−0.0041 (13)
C9	0.0430 (18)	0.0408 (16)	0.0280 (14)	−0.0024 (13)	0.0085 (13)	−0.0018 (13)
C10	0.0418 (17)	0.0370 (15)	0.0302 (15)	0.0013 (13)	0.0044 (12)	−0.0003 (12)
C11	0.0399 (18)	0.0410 (16)	0.0404 (17)	0.0012 (13)	0.0098 (14)	−0.0043 (14)
C12	0.0464 (19)	0.0520 (19)	0.0375 (17)	−0.0042 (15)	0.0016 (14)	−0.0060 (14)
C13	0.0449 (19)	0.056 (2)	0.0424 (18)	0.0007 (15)	−0.0023 (14)	0.0041 (15)
C14	0.0495 (19)	0.0385 (16)	0.0440 (17)	0.0040 (14)	0.0094 (15)	0.0053 (14)

Br1—C11	1.898 (3)	C4—H4	0.93
Cl1—C5	1.742 (3)	C5—C6	1.377 (4)
Cl2—C3	1.731 (3)	C6—H6	0.93
N1—C7	1.272 (3)	C7—H7	0.93
N1—N2	1.372 (3)	C8—C9	1.490 (4)
N2—C8	1.362 (3)	C9—C14	1.387 (4)
N2—H2	0.893 (10)	C9—C10	1.388 (3)
O1—C2	1.345 (3)	C10—C11	1.381 (4)
O1—H1	0.82	C10—H10	0.93
O2—C8	1.227 (3)	C11—C12	1.377 (4)
C1—C6	1.397 (4)	C12—C13	1.375 (4)
C1—C2	1.410 (4)	C12—H12	0.93
C1—C7	1.458 (4)	C13—C14	1.381 (4)
C2—C3	1.391 (4)	C13—H13	0.93
C3—C4	1.370 (3)	C14—H14	0.93
C4—C5	1.377 (4)
C7—N1—N2	117.7 (2)	N1—C7—H7	120.3
C8—N2—N1	116.9 (2)	C1—C7—H7	120.3
C8—N2—H2	120 (2)	O2—C8—N2	122.4 (2)
N1—N2—H2	121 (2)	O2—C8—C9	122.6 (2)
C2—O1—H1	109.5	N2—C8—C9	115.0 (2)
C6—C1—C2	119.5 (3)	C14—C9—C10	119.9 (3)
C6—C1—C7	119.3 (3)	C14—C9—C8	123.1 (2)
C2—C1—C7	121.1 (2)	C10—C9—C8	117.0 (2)
O1—C2—C3	118.4 (2)	C11—C10—C9	118.8 (3)
O1—C2—C1	123.3 (3)	C11—C10—H10	120.6
C3—C2—C1	118.3 (2)	C9—C10—H10	120.6
C4—C3—C2	121.7 (3)	C12—C11—C10	121.6 (3)
C4—C3—Cl2	119.4 (2)	C12—C11—Br1	119.9 (2)
C2—C3—Cl2	118.9 (2)	C10—C11—Br1	118.5 (2)
C3—C4—C5	119.8 (3)	C13—C12—C11	119.4 (3)
C3—C4—H4	120.1	C13—C12—H12	120.3
C5—C4—H4	120.1	C11—C12—H12	120.3
C4—C5—C6	120.5 (3)	C12—C13—C14	120.2 (3)
C4—C5—Cl1	119.4 (2)	C12—C13—H13	119.9
C6—C5—Cl1	120.1 (2)	C14—C13—H13	119.9
C5—C6—C1	120.2 (3)	C13—C14—C9	120.2 (3)
C5—C6—H6	119.9	C13—C14—H14	119.9
C1—C6—H6	119.9	C9—C14—H14	119.9
N1—C7—C1	119.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.598 (3)	145
N2—H2···O2i	0.89 (1)	2.03 (1)	2.898 (3)	165 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.88	2.598 (3)	145
N2—H2⋯O2i	0.89 (1)	2.03 (1)	2.898 (3)	165 (3)

Symmetry code: (i) .