(E)-N'-(3,5-Dibromo-2-hydroxy-benzyl-idene)-4-hydroxy-benzohydrazide monohydrate.

The title compound, C(14)H(10)Br(2)N(2)O(3)·H(2)O, was synthesized by the reaction of 3,5-dibromo-2-hydroxy-benzaldehyde with an equimolar amount of 4-hydroxy-benzohydrazide in methanol. The structure comprises a Schiff base unit and a water mol-ecule of crystallization. The dihedral angle between the benzene rings in the Schiff base is 1.3 (3)°. In the crystal structure, mol-ecules are linked through inter-molecular O-H⋯O and N-H⋯O hydrogen bonds, with the water mol-ecule serving as both donor and acceptor. As a result, layers are formed, which are approximately parallel to the bc plane.

Related literature

For related structures, see: Cao (2007a ▶,b ▶); Yang et al. (2008 ▶).

Experimental

Crystal data

C14H10Br2N2O3·H2O

M = 432.08

Monoclinic,

a = 6.9840 (16) Å

b = 12.678 (3) Å

c = 17.722 (4) Å

β = 96.999 (4)°

V = 1557.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 5.22 mm−1

T = 298 (2) K

0.23 × 0.23 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.307, T max = 0.318

12695 measured reflections

3366 independent reflections

2045 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.106

S = 0.99

3366 reflections

210 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.42 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/S1600536808030304/bh2193sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030304/bh2193Isup2.hkl

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

C14H10Br2N2O3·H2O	F(000) = 848
Mr = 432.08	Dx = 1.843 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1545 reflections
a = 6.9840 (16) Å	θ = 2.3–24.9°
b = 12.678 (3) Å	µ = 5.22 mm−1
c = 17.722 (4) Å	T = 298 K
β = 96.999 (4)°	Block, colourless
V = 1557.4 (6) Å3	0.23 × 0.23 × 0.22 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3366 independent reflections
Radiation source: fine-focus sealed tube	2045 reflections with I > 2σ(I)
graphite	Rint = 0.075
ω scans	θmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→8
Tmin = 0.308, Tmax = 0.318	k = −16→15
12695 measured reflections	l = −22→22

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0361P)2] where P = (Fo2 + 2Fc2)/3
3366 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.42 e Å−3
4 restraints	Δρmin = −0.42 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Br1	0.07183 (8)	0.86697 (4)	−0.00493 (3)	0.0601 (2)
Br2	0.05286 (8)	0.71867 (5)	−0.30593 (3)	0.0664 (2)
O1	0.1871 (5)	0.6446 (2)	0.03203 (16)	0.0405 (7)
H1	0.2190	0.5834	0.0420	0.061*
O2	0.3386 (4)	0.4075 (2)	0.14777 (16)	0.0426 (8)
O3	0.5946 (6)	−0.0702 (2)	0.20309 (16)	0.0594 (10)
H3	0.6086	−0.0733	0.2497	0.089*
O4	0.4571 (5)	0.2539 (3)	0.39995 (18)	0.0494 (8)
N1	0.2698 (5)	0.4520 (3)	0.00247 (19)	0.0323 (8)
N2	0.3257 (5)	0.3529 (3)	0.02714 (19)	0.0336 (8)
C1	0.1784 (6)	0.5746 (3)	−0.0955 (2)	0.0301 (10)
C2	0.1564 (6)	0.6572 (3)	−0.0440 (2)	0.0336 (10)
C3	0.1013 (6)	0.7560 (3)	−0.0737 (3)	0.0388 (11)
C4	0.0691 (6)	0.7749 (4)	−0.1503 (3)	0.0422 (11)
H4	0.0323	0.8414	−0.1687	0.051*
C5	0.0927 (6)	0.6928 (4)	−0.1997 (2)	0.0385 (11)
C6	0.1470 (6)	0.5942 (4)	−0.1731 (2)	0.0398 (11)
H6	0.1628	0.5401	−0.2073	0.048*
C7	0.2368 (6)	0.4704 (3)	−0.0687 (2)	0.0358 (10)
H7	0.2504	0.4166	−0.1033	0.043*
C8	0.3580 (6)	0.3355 (3)	0.1033 (2)	0.0311 (10)
C9	0.4152 (6)	0.2264 (3)	0.1270 (2)	0.0292 (9)
C10	0.4475 (7)	0.2041 (3)	0.2037 (2)	0.0430 (12)
H10	0.4294	0.2573	0.2383	0.052*
C11	0.5056 (7)	0.1059 (3)	0.2311 (2)	0.0438 (12)
H11	0.5262	0.0933	0.2832	0.053*
C12	0.5325 (7)	0.0275 (3)	0.1807 (2)	0.0385 (11)
C13	0.4980 (7)	0.0477 (3)	0.1040 (2)	0.0528 (14)
H13	0.5146	−0.0059	0.0696	0.063*
C14	0.4397 (7)	0.1452 (3)	0.0773 (2)	0.0462 (12)
H14	0.4163	0.1569	0.0252	0.055*
H2	0.356 (7)	0.307 (3)	−0.008 (2)	0.080*
H4A	0.436 (6)	0.309 (3)	0.373 (3)	0.080*
H4B	0.5787 (19)	0.245 (4)	0.408 (3)	0.080*

	U11	U22	U33	U12	U13	U23
Br1	0.0799 (4)	0.0359 (3)	0.0643 (4)	0.0158 (3)	0.0076 (3)	−0.0051 (3)
Br2	0.0707 (4)	0.0883 (5)	0.0380 (3)	0.0029 (3)	−0.0022 (2)	0.0233 (3)
O1	0.061 (2)	0.0292 (17)	0.0304 (16)	0.0048 (16)	0.0005 (15)	0.0034 (13)
O2	0.066 (2)	0.0267 (16)	0.0348 (17)	0.0075 (15)	0.0035 (15)	−0.0053 (14)
O3	0.122 (3)	0.0215 (17)	0.0333 (18)	0.0134 (19)	0.003 (2)	0.0046 (14)
O4	0.070 (2)	0.041 (2)	0.0359 (18)	−0.0058 (18)	0.0031 (17)	0.0069 (15)
N1	0.035 (2)	0.026 (2)	0.034 (2)	0.0008 (16)	0.0007 (16)	0.0021 (16)
N2	0.046 (2)	0.023 (2)	0.031 (2)	0.0049 (17)	0.0024 (17)	0.0037 (15)
C1	0.032 (2)	0.032 (2)	0.026 (2)	0.0011 (19)	0.0028 (18)	0.0022 (19)
C2	0.032 (2)	0.035 (3)	0.033 (2)	0.001 (2)	0.0032 (19)	0.004 (2)
C3	0.039 (3)	0.030 (2)	0.047 (3)	0.004 (2)	0.004 (2)	0.001 (2)
C4	0.041 (3)	0.035 (3)	0.050 (3)	0.006 (2)	0.001 (2)	0.016 (2)
C5	0.035 (2)	0.049 (3)	0.030 (2)	0.000 (2)	0.0011 (19)	0.015 (2)
C6	0.042 (3)	0.045 (3)	0.032 (2)	0.004 (2)	0.001 (2)	0.000 (2)
C7	0.043 (3)	0.032 (3)	0.032 (2)	0.003 (2)	0.002 (2)	−0.0007 (19)
C8	0.029 (2)	0.029 (2)	0.034 (2)	−0.0019 (19)	0.0004 (19)	0.000 (2)
C9	0.034 (2)	0.023 (2)	0.030 (2)	−0.0003 (19)	0.0010 (18)	0.0003 (18)
C10	0.067 (3)	0.033 (3)	0.030 (2)	0.007 (2)	0.006 (2)	−0.010 (2)
C11	0.073 (3)	0.032 (3)	0.026 (2)	0.009 (2)	0.006 (2)	0.001 (2)
C12	0.064 (3)	0.019 (2)	0.033 (3)	0.003 (2)	0.009 (2)	0.0036 (19)
C13	0.104 (4)	0.025 (3)	0.029 (3)	0.014 (3)	0.006 (3)	−0.008 (2)
C14	0.081 (4)	0.030 (3)	0.026 (2)	0.009 (3)	0.001 (2)	−0.001 (2)

Br1—C3	1.888 (4)	C3—C4	1.371 (6)
Br2—C5	1.897 (4)	C4—C5	1.382 (6)
O1—C2	1.348 (5)	C4—H4	0.9300
O1—H1	0.8200	C5—C6	1.374 (6)
O2—C8	1.225 (5)	C6—H6	0.9300
O3—C12	1.355 (5)	C7—H7	0.9300
O3—H3	0.8200	C8—C9	1.486 (5)
O4—H4A	0.847 (10)	C9—C14	1.379 (5)
O4—H4B	0.851 (10)	C9—C10	1.379 (6)
N1—C7	1.275 (5)	C10—C11	1.380 (6)
N1—N2	1.371 (4)	C10—H10	0.9300
N2—C8	1.359 (5)	C11—C12	1.365 (6)
N2—H2	0.898 (10)	C11—H11	0.9300
C1—C6	1.387 (5)	C12—C13	1.375 (6)
C1—C2	1.411 (6)	C13—C14	1.368 (6)
C1—C7	1.446 (6)	C13—H13	0.9300
C2—C3	1.395 (6)	C14—H14	0.9300
C2—O1—H1	109.5	N1—C7—C1	120.2 (4)
C12—O3—H3	109.5	N1—C7—H7	119.9
H4A—O4—H4B	108 (2)	C1—C7—H7	119.9
C7—N1—N2	119.5 (4)	O2—C8—N2	120.0 (4)
C8—N2—N1	118.2 (3)	O2—C8—C9	123.9 (4)
C8—N2—H2	124 (4)	N2—C8—C9	116.1 (4)
N1—N2—H2	117 (4)	C14—C9—C10	117.3 (4)
C6—C1—C2	119.4 (4)	C14—C9—C8	124.3 (4)
C6—C1—C7	119.6 (4)	C10—C9—C8	118.4 (4)
C2—C1—C7	120.9 (4)	C9—C10—C11	122.5 (4)
O1—C2—C3	119.1 (4)	C9—C10—H10	118.7
O1—C2—C1	122.8 (4)	C11—C10—H10	118.7
C3—C2—C1	118.1 (4)	C12—C11—C10	119.0 (4)
C4—C3—C2	122.3 (4)	C12—C11—H11	120.5
C4—C3—Br1	119.5 (3)	C10—C11—H11	120.5
C2—C3—Br1	118.2 (3)	O3—C12—C11	122.6 (4)
C3—C4—C5	118.6 (4)	O3—C12—C13	118.1 (4)
C3—C4—H4	120.7	C11—C12—C13	119.3 (4)
C5—C4—H4	120.7	C14—C13—C12	121.3 (4)
C6—C5—C4	121.1 (4)	C14—C13—H13	119.4
C6—C5—Br2	120.0 (4)	C12—C13—H13	119.4
C4—C5—Br2	118.9 (3)	C13—C14—C9	120.6 (4)
C5—C6—C1	120.5 (4)	C13—C14—H14	119.7
C5—C6—H6	119.7	C9—C14—H14	119.7
C1—C6—H6	119.7

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.578 (4)	146.
O3—H3···O2i	0.82	1.83	2.642 (4)	173.
O4—H4A···O3ii	0.85 (1)	2.04 (1)	2.878 (4)	171 (5)
O4—H4B···O1i	0.85 (1)	2.24 (3)	2.969 (5)	144 (4)
N2—H2···O4iii	0.90 (1)	2.01 (2)	2.874 (5)	162 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.86	2.578 (4)	146
O3—H3⋯O2i	0.82	1.83	2.642 (4)	173
O4—H4A⋯O3ii	0.847 (10)	2.038 (14)	2.878 (4)	171 (5)
O4—H4B⋯O1i	0.851 (10)	2.24 (3)	2.969 (5)	144 (4)
N2—H2⋯O4iii	0.898 (10)	2.01 (2)	2.874 (5)	162 (5)

Symmetry codes: (i) ; (ii) ; (iii) .