4-Chloro-N'-(3,5-dibromo-2-hy-droxy-benzyl-idene)benzohydrazide.

The asymmetric unit of the title compound, C(14)H(9)Br(2)ClN(2)O(2), contains two independent mol-ecules. Both mol-ecules adopt an E configuration about the C=N bond. The dihedral angles between the benzene rings are 30.0 (2) and 51.6 (2)° in the two mol-ecules. In the crystal, mol-ecules are linked through N-H⋯O hydrogen bonds, forming chains along the b axis. In addition, there is an intra-molecular O-H⋯N hydrogen bond in each mol-ecule.

Related literature

For the biological properties of hydrazone compounds, see: Ajani et al. (2010 ▶); Angelusiu et al. (2010 ▶); Zhang et al. (2010 ▶); Horiuchi et al. (2009 ▶). For the crystal structures of similar hydrazone compounds, see: Ban (2010 ▶); Hussain et al. (2010 ▶); Shalash et al. (2010 ▶); Khaledi et al. (2009 ▶). For related structures reported recently by the author, see: Zhang (2011 ▶, 2012 ▶).

Experimental

Crystal data

C14H9Br2ClN2O2

M = 432.50

Monoclinic,

a = 21.0503 (19) Å

b = 9.9895 (11) Å

c = 30.185 (2) Å

β = 101.836 (2)°

V = 6212.4 (10) Å3

Z = 16

Mo Kα radiation

μ = 5.40 mm−1

T = 298 K

0.20 × 0.18 × 0.17 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.412, T max = 0.461

21727 measured reflections

5775 independent reflections

2828 reflections with I > 2σ(I)

R int = 0.093

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.105

S = 0.95

5775 reflections

389 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536812009786/lh5429sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009786/lh5429Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009786/lh5429Isup3.cml

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

C14H9Br2ClN2O2	F(000) = 3360
Mr = 432.50	Dx = 1.850 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2652 reflections
a = 21.0503 (19) Å	θ = 2.3–24.3°
b = 9.9895 (11) Å	µ = 5.40 mm−1
c = 30.185 (2) Å	T = 298 K
β = 101.836 (2)°	Block, colorless
V = 6212.4 (10) Å3	0.20 × 0.18 × 0.17 mm
Z = 16

Bruker APEXII CCD area-detector diffractometer	5775 independent reflections
Radiation source: fine-focus sealed tube	2828 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.093
ω scans	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→25
Tmin = 0.412, Tmax = 0.461	k = −12→12
21727 measured reflections	l = −36→33

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ2(Fo2) + (0.0375P)2] where P = (Fo2 + 2Fc2)/3
5775 reflections	(Δ/σ)max = 0.001
389 parameters	Δρmax = 0.53 e Å−3
2 restraints	Δρmin = −0.59 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	0.59984 (4)	−0.15649 (7)	0.50684 (2)	0.0893 (3)
Br2	0.60096 (5)	0.40530 (8)	0.51878 (3)	0.1266 (4)
Br3	0.16100 (3)	0.32156 (6)	0.13346 (2)	0.0621 (2)
Br4	0.13920 (3)	0.88180 (6)	0.11656 (2)	0.0662 (2)
Cl1	0.28553 (8)	0.0539 (2)	0.08490 (5)	0.0867 (6)
Cl2	0.69898 (8)	0.5736 (2)	0.42951 (6)	0.0988 (7)
N1	0.48103 (18)	0.0501 (4)	0.34395 (14)	0.0364 (10)
N2	0.4503 (2)	0.0679 (4)	0.29989 (14)	0.0393 (11)
N3	0.3518 (2)	0.5527 (4)	0.25814 (14)	0.0429 (11)
N4	0.4089 (2)	0.5744 (4)	0.28790 (15)	0.0452 (12)
O1	0.5259 (2)	−0.0988 (3)	0.41356 (11)	0.0564 (11)
H1	0.5103	−0.0831	0.3869	0.085*
O2	0.44485 (17)	−0.1529 (3)	0.28785 (12)	0.0522 (10)
O3	0.26677 (17)	0.3947 (3)	0.21220 (12)	0.0469 (9)
H3	0.3028	0.4132	0.2271	0.070*
O4	0.43685 (17)	0.3578 (3)	0.28369 (11)	0.0496 (10)
C1	0.5296 (2)	0.1408 (5)	0.41481 (18)	0.0409 (14)
C2	0.5433 (2)	0.0165 (5)	0.43546 (18)	0.0444 (14)
C3	0.5777 (3)	0.0117 (6)	0.48000 (19)	0.0544 (16)
C4	0.5949 (3)	0.1262 (6)	0.50448 (19)	0.0688 (19)
H4A	0.6173	0.1215	0.5344	0.083*
C5	0.5787 (3)	0.2482 (6)	0.4843 (2)	0.0661 (19)
C6	0.5472 (3)	0.2557 (5)	0.44034 (19)	0.0547 (16)
H6	0.5373	0.3392	0.4271	0.066*
C7	0.4980 (2)	0.1532 (5)	0.36838 (18)	0.0430 (14)
H7	0.4896	0.2380	0.3558	0.052*
C8	0.4314 (2)	−0.0407 (5)	0.27356 (18)	0.0385 (13)
C9	0.3945 (2)	−0.0126 (5)	0.22721 (17)	0.0355 (13)
C10	0.3549 (2)	0.0978 (5)	0.21643 (18)	0.0464 (15)
H10	0.3515	0.1596	0.2389	0.056*
C11	0.3200 (3)	0.1184 (6)	0.1727 (2)	0.0550 (16)
H11	0.2930	0.1924	0.1657	0.066*
C12	0.3265 (3)	0.0269 (6)	0.13990 (18)	0.0499 (15)
C13	0.3631 (3)	−0.0858 (6)	0.1497 (2)	0.0564 (16)
H13	0.3650	−0.1487	0.1273	0.068*
C14	0.3976 (2)	−0.1056 (5)	0.19342 (19)	0.0460 (14)
H14	0.4231	−0.1818	0.2003	0.055*
C15	0.2601 (2)	0.6341 (5)	0.20665 (17)	0.0387 (13)
C16	0.2386 (2)	0.5064 (5)	0.19194 (17)	0.0373 (13)
C17	0.1875 (2)	0.4942 (5)	0.15544 (17)	0.0393 (13)
C18	0.1587 (2)	0.6050 (6)	0.13239 (17)	0.0460 (14)
H18	0.1263	0.5948	0.1066	0.055*
C19	0.1784 (3)	0.7297 (5)	0.14789 (17)	0.0421 (14)
C20	0.2292 (2)	0.7460 (5)	0.18405 (16)	0.0412 (14)
H20	0.2431	0.8316	0.1935	0.049*
C21	0.3177 (2)	0.6530 (5)	0.24191 (16)	0.0417 (14)
H21	0.3297	0.7386	0.2526	0.050*
C22	0.4500 (2)	0.4694 (5)	0.29903 (17)	0.0400 (14)
C23	0.5113 (3)	0.5008 (5)	0.33136 (16)	0.0351 (13)
C24	0.5150 (3)	0.5908 (5)	0.36667 (17)	0.0451 (15)
H24	0.4781	0.6385	0.3696	0.054*
C25	0.5719 (3)	0.6111 (5)	0.39751 (19)	0.0507 (15)
H25	0.5731	0.6693	0.4217	0.061*
C26	0.6262 (3)	0.5457 (6)	0.3924 (2)	0.0537 (16)
C27	0.6246 (3)	0.4561 (6)	0.3576 (2)	0.0648 (18)
H27	0.6620	0.4107	0.3545	0.078*
C28	0.5668 (3)	0.4343 (5)	0.32730 (18)	0.0510 (15)
H28	0.5656	0.3736	0.3038	0.061*
H2	0.440 (2)	0.150 (2)	0.2886 (14)	0.039 (15)*
H4	0.4239 (18)	0.6586 (17)	0.2928 (13)	0.028 (13)*

	U11	U22	U33	U12	U13	U23
Br1	0.1524 (8)	0.0620 (5)	0.0432 (4)	0.0235 (5)	−0.0042 (4)	0.0114 (4)
Br2	0.2209 (11)	0.0680 (5)	0.0661 (6)	−0.0248 (6)	−0.0282 (6)	−0.0228 (4)
Br3	0.0642 (4)	0.0549 (4)	0.0575 (4)	−0.0059 (3)	−0.0101 (3)	−0.0099 (3)
Br4	0.0726 (5)	0.0615 (4)	0.0599 (4)	0.0200 (3)	0.0025 (3)	0.0202 (4)
Cl1	0.0802 (12)	0.1304 (16)	0.0417 (10)	−0.0018 (12)	−0.0056 (9)	0.0045 (10)
Cl2	0.0554 (11)	0.1279 (17)	0.0980 (15)	−0.0097 (11)	−0.0196 (10)	−0.0172 (13)
N1	0.043 (3)	0.033 (3)	0.029 (3)	−0.004 (2)	−0.002 (2)	0.005 (2)
N2	0.054 (3)	0.025 (3)	0.035 (3)	0.003 (2)	0.000 (2)	0.000 (2)
N3	0.051 (3)	0.032 (3)	0.040 (3)	0.001 (2)	−0.004 (2)	0.005 (2)
N4	0.048 (3)	0.026 (3)	0.050 (3)	−0.004 (2)	−0.016 (2)	0.003 (2)
O1	0.093 (3)	0.035 (2)	0.035 (2)	0.003 (2)	−0.001 (2)	0.0007 (18)
O2	0.065 (3)	0.028 (2)	0.058 (3)	−0.0016 (19)	−0.002 (2)	0.0050 (19)
O3	0.054 (3)	0.034 (2)	0.046 (3)	−0.0019 (18)	−0.0069 (19)	−0.0033 (18)
O4	0.072 (3)	0.024 (2)	0.045 (2)	−0.0014 (18)	−0.009 (2)	−0.0068 (17)
C1	0.047 (3)	0.032 (3)	0.042 (4)	0.002 (3)	0.007 (3)	0.001 (3)
C2	0.052 (4)	0.033 (3)	0.047 (4)	0.003 (3)	0.006 (3)	0.000 (3)
C3	0.074 (4)	0.050 (4)	0.036 (4)	0.004 (3)	0.002 (3)	0.009 (3)
C4	0.097 (5)	0.069 (5)	0.030 (4)	−0.006 (4)	−0.010 (3)	−0.010 (4)
C5	0.099 (5)	0.051 (4)	0.038 (4)	−0.007 (4)	−0.011 (4)	−0.007 (3)
C6	0.079 (5)	0.038 (4)	0.045 (4)	−0.004 (3)	0.006 (3)	0.003 (3)
C7	0.054 (4)	0.033 (3)	0.040 (4)	−0.008 (3)	0.003 (3)	0.005 (3)
C8	0.040 (3)	0.023 (3)	0.050 (4)	−0.001 (3)	0.005 (3)	−0.001 (3)
C9	0.029 (3)	0.032 (3)	0.046 (4)	−0.003 (3)	0.007 (3)	−0.002 (3)
C10	0.053 (4)	0.041 (3)	0.042 (4)	0.007 (3)	0.000 (3)	−0.006 (3)
C11	0.057 (4)	0.049 (4)	0.054 (4)	0.006 (3)	0.000 (3)	0.001 (3)
C12	0.044 (4)	0.069 (4)	0.035 (4)	−0.011 (3)	0.003 (3)	0.001 (3)
C13	0.058 (4)	0.059 (4)	0.048 (4)	−0.007 (3)	0.004 (3)	−0.016 (3)
C14	0.044 (4)	0.038 (3)	0.052 (4)	0.005 (3)	0.001 (3)	−0.012 (3)
C15	0.043 (3)	0.039 (3)	0.035 (3)	0.003 (3)	0.009 (3)	0.003 (3)
C16	0.043 (3)	0.030 (3)	0.037 (3)	0.004 (3)	0.004 (3)	0.001 (3)
C17	0.037 (3)	0.046 (3)	0.034 (3)	0.003 (3)	0.004 (3)	−0.005 (3)
C18	0.045 (4)	0.062 (4)	0.028 (3)	0.008 (3)	0.001 (3)	0.004 (3)
C19	0.051 (4)	0.044 (4)	0.029 (3)	0.010 (3)	0.003 (3)	0.010 (3)
C20	0.049 (4)	0.033 (3)	0.041 (4)	0.005 (3)	0.009 (3)	0.009 (3)
C21	0.055 (4)	0.033 (3)	0.035 (3)	−0.008 (3)	0.003 (3)	0.003 (3)
C22	0.049 (4)	0.034 (3)	0.033 (3)	−0.002 (3)	0.000 (3)	0.006 (3)
C23	0.047 (4)	0.027 (3)	0.029 (3)	0.002 (3)	0.003 (3)	0.006 (2)
C24	0.052 (4)	0.031 (3)	0.045 (4)	0.010 (3)	−0.009 (3)	−0.006 (3)
C25	0.057 (4)	0.037 (3)	0.053 (4)	−0.007 (3)	0.000 (3)	−0.005 (3)
C26	0.042 (4)	0.056 (4)	0.058 (4)	−0.005 (3)	−0.001 (3)	0.005 (3)
C27	0.055 (4)	0.071 (5)	0.071 (5)	0.015 (4)	0.020 (4)	0.003 (4)
C28	0.058 (4)	0.054 (4)	0.042 (4)	−0.001 (3)	0.010 (3)	−0.003 (3)

Br1—C3	1.882 (5)	C9—C10	1.380 (6)
Br2—C5	1.888 (6)	C9—C14	1.391 (6)
Br3—C17	1.890 (5)	C10—C11	1.389 (7)
Br4—C19	1.888 (5)	C10—H10	0.9300
Cl1—C12	1.727 (5)	C11—C12	1.374 (7)
Cl2—C26	1.724 (6)	C11—H11	0.9300
N1—C7	1.274 (5)	C12—C13	1.363 (7)
N1—N2	1.366 (5)	C13—C14	1.383 (7)
N2—C8	1.356 (6)	C13—H13	0.9300
N2—H2	0.897 (10)	C14—H14	0.9300
N3—C21	1.271 (5)	C15—C16	1.396 (6)
N3—N4	1.362 (5)	C15—C20	1.398 (6)
N4—C22	1.357 (6)	C15—C21	1.452 (7)
N4—H4	0.900 (10)	C16—C17	1.379 (6)
O1—C2	1.341 (5)	C17—C18	1.379 (6)
O1—H1	0.8200	C18—C19	1.364 (7)
O2—C8	1.213 (5)	C18—H18	0.9300
O3—C16	1.349 (5)	C19—C20	1.373 (7)
O3—H3	0.8200	C20—H20	0.9300
O4—C22	1.217 (5)	C21—H21	0.9300
C1—C6	1.390 (6)	C22—C23	1.484 (6)
C1—C2	1.393 (6)	C23—C28	1.371 (7)
C1—C7	1.428 (7)	C23—C24	1.384 (6)
C2—C3	1.390 (7)	C24—C25	1.374 (7)
C3—C4	1.370 (7)	C24—H24	0.9300
C4—C5	1.374 (7)	C25—C26	1.352 (7)
C4—H4A	0.9300	C25—H25	0.9300
C5—C6	1.357 (7)	C26—C27	1.376 (7)
C6—H6	0.9300	C27—C28	1.380 (7)
C7—H7	0.9300	C27—H27	0.9300
C8—C9	1.482 (6)	C28—H28	0.9300
C7—N1—N2	118.6 (4)	C12—C13—H13	120.4
C8—N2—N1	119.3 (4)	C14—C13—H13	120.4
C8—N2—H2	119 (3)	C13—C14—C9	120.6 (5)
N1—N2—H2	121 (3)	C13—C14—H14	119.7
C21—N3—N4	118.8 (4)	C9—C14—H14	119.7
C22—N4—N3	118.2 (4)	C16—C15—C20	119.2 (5)
C22—N4—H4	120 (3)	C16—C15—C21	121.3 (5)
N3—N4—H4	119 (3)	C20—C15—C21	119.3 (5)
C2—O1—H1	109.5	O3—C16—C17	119.2 (5)
C16—O3—H3	109.5	O3—C16—C15	121.9 (4)
C6—C1—C2	118.7 (5)	C17—C16—C15	119.0 (5)
C6—C1—C7	119.3 (5)	C18—C17—C16	121.5 (5)
C2—C1—C7	121.9 (5)	C18—C17—Br3	119.2 (4)
O1—C2—C3	118.8 (5)	C16—C17—Br3	119.1 (4)
O1—C2—C1	122.3 (5)	C19—C18—C17	119.3 (5)
C3—C2—C1	118.9 (5)	C19—C18—H18	120.4
C4—C3—C2	121.3 (5)	C17—C18—H18	120.4
C4—C3—Br1	119.9 (4)	C18—C19—C20	120.9 (5)
C2—C3—Br1	118.8 (4)	C18—C19—Br4	119.5 (4)
C3—C4—C5	119.1 (5)	C20—C19—Br4	119.5 (4)
C3—C4—H4A	120.4	C19—C20—C15	120.1 (5)
C5—C4—H4A	120.4	C19—C20—H20	119.9
C6—C5—C4	120.6 (5)	C15—C20—H20	119.9
C6—C5—Br2	120.6 (5)	N3—C21—C15	120.1 (5)
C4—C5—Br2	118.8 (4)	N3—C21—H21	120.0
C5—C6—C1	121.2 (5)	C15—C21—H21	120.0
C5—C6—H6	119.4	O4—C22—N4	122.0 (5)
C1—C6—H6	119.4	O4—C22—C23	122.9 (5)
N1—C7—C1	121.1 (5)	N4—C22—C23	115.1 (5)
N1—C7—H7	119.5	C28—C23—C24	118.0 (5)
C1—C7—H7	119.5	C28—C23—C22	118.8 (5)
O2—C8—N2	120.8 (5)	C24—C23—C22	123.2 (5)
O2—C8—C9	123.4 (5)	C25—C24—C23	121.3 (5)
N2—C8—C9	115.8 (4)	C25—C24—H24	119.3
C10—C9—C14	118.6 (5)	C23—C24—H24	119.3
C10—C9—C8	123.3 (5)	C26—C25—C24	119.5 (5)
C14—C9—C8	118.1 (5)	C26—C25—H25	120.2
C9—C10—C11	121.2 (5)	C24—C25—H25	120.2
C9—C10—H10	119.4	C25—C26—C27	120.8 (5)
C11—C10—H10	119.4	C25—C26—Cl2	120.5 (5)
C12—C11—C10	118.4 (5)	C27—C26—Cl2	118.8 (5)
C12—C11—H11	120.8	C26—C27—C28	119.3 (6)
C10—C11—H11	120.8	C26—C27—H27	120.3
C13—C12—C11	121.9 (5)	C28—C27—H27	120.3
C13—C12—Cl1	119.1 (5)	C23—C28—C27	121.0 (5)
C11—C12—Cl1	119.0 (5)	C23—C28—H28	119.5
C12—C13—C14	119.3 (5)	C27—C28—H28	119.5

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O2i	0.90 (1)	1.95 (2)	2.827 (5)	166 (4)
N2—H2···O4	0.90 (1)	2.08 (2)	2.941 (5)	160 (4)
O3—H3···N3	0.82	1.87	2.569 (5)	143
O1—H1···N1	0.82	1.87	2.590 (5)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O2i	0.90 (1)	1.95 (2)	2.827 (5)	166 (4)
N2—H2⋯O4	0.90 (1)	2.08 (2)	2.941 (5)	160 (4)
O3—H3⋯N3	0.82	1.87	2.569 (5)	143
O1—H1⋯N1	0.82	1.87	2.590 (5)	146

Symmetry code: (i) .