(E)-N'-(5-Bromo-2-hy-droxy-benzyl-idene)-3,5-dihy-droxy-benzohydrazide monohydrate.

The Schiff base mol-ecule in the title compound, C(14)H(11)BrN(2)O(4)·H(2)O, is almost planar with an r.m.s. deviation for the non-H atoms of 0.16 Å. In the crystal structure, the Schiff base mol-ecules and the water mol-ecules are linked together by inter-molecular N-H⋯O and O-H⋯O hydrogen bonds, leading to layers parallel to the bc plane. An intra-molecular O-H⋯N hydrogen bond involving the imine N atom and a hy-droxy substituent is also observed.

Related literature

For the isotypic Cl analogue C14H11ClN2O4·H2O, see: Deng et al. (2009 ▶).

Experimental

Crystal data

C14H11BrN2O4·H2O

M = 369.17

Monoclinic,

a = 13.5685 (3) Å

b = 8.0532 (2) Å

c = 13.2447 (2) Å

β = 100.186 (1)°

V = 1424.44 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.91 mm−1

T = 296 K

0.58 × 0.33 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.283, T max = 0.845

9148 measured reflections

2579 independent reflections

2183 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.077

S = 1.04

2579 reflections

217 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.56 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810027856/bh2299sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027856/bh2299Isup2.hkl

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

C14H11BrN2O4·H2O	F(000) = 744
Mr = 369.17	Dx = 1.721 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3109 reflections
a = 13.5685 (3) Å	θ = 3.0–26.1°
b = 8.0532 (2) Å	µ = 2.91 mm−1
c = 13.2447 (2) Å	T = 296 K
β = 100.186 (1)°	Plate, yellow
V = 1424.44 (5) Å3	0.58 × 0.33 × 0.06 mm
Z = 4

Bruker APEXII CCD diffractometer	2579 independent reflections
Radiation source: fine-focus sealed tube	2183 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 25.3°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
Tmin = 0.283, Tmax = 0.845	k = −9→9
9148 measured reflections	l = −15→15

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0328P)2 + 0.7124P] where P = (Fo2 + 2Fc2)/3
2579 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.45 e Å−3
6 restraints	Δρmin = −0.56 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Br1	0.54976 (2)	0.19522 (4)	0.67677 (2)	0.05405 (13)
O1	0.25489 (15)	0.4914 (3)	0.33122 (13)	0.0448 (5)
H1	0.210 (2)	0.542 (4)	0.351 (2)	0.067*
O8	−0.01522 (14)	0.6853 (2)	0.34596 (12)	0.0375 (4)
O11	−0.18429 (14)	0.9113 (2)	0.71231 (12)	0.0378 (4)
H11	−0.1355 (18)	0.868 (4)	0.749 (2)	0.057*
O13	−0.29944 (14)	1.0800 (2)	0.37286 (13)	0.0440 (5)
H13	−0.285 (3)	1.075 (4)	0.3181 (17)	0.066*
N1	0.15274 (14)	0.5993 (2)	0.47190 (14)	0.0279 (4)
N2	0.07629 (15)	0.6835 (2)	0.50575 (14)	0.0277 (4)
H2N	0.088 (2)	0.712 (3)	0.5686 (14)	0.033*
C1	0.31939 (19)	0.4270 (3)	0.41219 (17)	0.0312 (5)
C2	0.3994 (2)	0.3354 (3)	0.39071 (19)	0.0402 (6)
H2	0.4072	0.3208	0.3229	0.048*
C3	0.4676 (2)	0.2657 (3)	0.4683 (2)	0.0391 (6)
H3	0.5211	0.2037	0.4534	0.047*
C4	0.45524 (18)	0.2895 (3)	0.56914 (18)	0.0330 (6)
C5	0.37678 (18)	0.3807 (3)	0.59223 (17)	0.0319 (5)
H5	0.3701	0.3951	0.6603	0.038*
C6	0.30662 (17)	0.4524 (3)	0.51387 (16)	0.0278 (5)
C7	0.22369 (18)	0.5450 (3)	0.54062 (17)	0.0300 (5)
H7	0.2219	0.5656	0.6094	0.036*
C8	−0.00598 (18)	0.7237 (3)	0.43815 (16)	0.0266 (5)
C9	−0.08615 (17)	0.8158 (3)	0.47789 (16)	0.0248 (5)
C10	−0.09485 (18)	0.8153 (3)	0.58150 (16)	0.0274 (5)
H10	−0.0499	0.7559	0.6293	0.033*
C11	−0.17126 (17)	0.9044 (3)	0.61131 (16)	0.0276 (5)
C12	−0.23974 (18)	0.9932 (3)	0.54147 (17)	0.0303 (5)
H12	−0.2908	1.0530	0.5632	0.036*
C13	−0.23079 (18)	0.9912 (3)	0.43882 (16)	0.0291 (5)
C14	−0.15405 (17)	0.9038 (3)	0.40695 (16)	0.0283 (5)
H14	−0.1479	0.9040	0.3381	0.034*
O2	0.12746 (16)	0.7432 (3)	0.72574 (13)	0.0428 (5)
H2A	0.091 (2)	0.772 (4)	0.764 (2)	0.064*
H2B	0.153 (3)	0.656 (3)	0.750 (2)	0.064*

	U11	U22	U33	U12	U13	U23
Br1	0.03931 (19)	0.0753 (2)	0.04679 (19)	0.02026 (15)	0.00548 (13)	0.01280 (14)
O1	0.0449 (12)	0.0626 (13)	0.0261 (9)	0.0149 (10)	0.0044 (8)	−0.0005 (8)
O8	0.0353 (10)	0.0545 (11)	0.0224 (8)	0.0033 (9)	0.0047 (7)	−0.0065 (7)
O11	0.0417 (11)	0.0525 (11)	0.0209 (8)	0.0101 (9)	0.0098 (7)	0.0018 (7)
O13	0.0447 (11)	0.0571 (12)	0.0291 (9)	0.0212 (10)	0.0033 (8)	0.0079 (8)
N1	0.0269 (11)	0.0292 (10)	0.0281 (10)	0.0012 (9)	0.0061 (8)	−0.0039 (8)
N2	0.0273 (11)	0.0341 (11)	0.0221 (9)	0.0035 (9)	0.0048 (8)	−0.0063 (8)
C1	0.0308 (13)	0.0351 (13)	0.0275 (12)	0.0001 (11)	0.0047 (10)	0.0000 (10)
C2	0.0397 (16)	0.0533 (17)	0.0302 (13)	0.0037 (13)	0.0133 (11)	−0.0057 (11)
C3	0.0316 (15)	0.0451 (15)	0.0431 (15)	0.0054 (12)	0.0135 (11)	−0.0041 (11)
C4	0.0266 (14)	0.0382 (14)	0.0338 (13)	0.0010 (11)	0.0039 (10)	0.0021 (10)
C5	0.0316 (14)	0.0382 (13)	0.0271 (12)	0.0016 (11)	0.0082 (10)	−0.0020 (10)
C6	0.0268 (13)	0.0294 (12)	0.0276 (11)	−0.0035 (10)	0.0058 (9)	−0.0041 (9)
C7	0.0306 (13)	0.0348 (13)	0.0251 (11)	0.0009 (11)	0.0066 (10)	−0.0049 (9)
C8	0.0278 (13)	0.0289 (12)	0.0233 (12)	−0.0034 (10)	0.0053 (9)	−0.0001 (9)
C9	0.0243 (12)	0.0269 (11)	0.0233 (11)	−0.0032 (9)	0.0041 (9)	−0.0015 (9)
C10	0.0290 (13)	0.0307 (12)	0.0216 (11)	0.0007 (10)	0.0015 (9)	0.0012 (9)
C11	0.0301 (13)	0.0315 (12)	0.0222 (11)	−0.0034 (10)	0.0072 (9)	−0.0009 (9)
C12	0.0290 (13)	0.0327 (13)	0.0304 (12)	0.0029 (10)	0.0080 (10)	−0.0006 (9)
C13	0.0289 (13)	0.0299 (12)	0.0271 (11)	0.0012 (10)	0.0008 (10)	0.0032 (9)
C14	0.0322 (14)	0.0340 (13)	0.0182 (10)	−0.0018 (11)	0.0034 (9)	−0.0002 (9)
O2	0.0497 (13)	0.0487 (11)	0.0308 (10)	0.0051 (10)	0.0093 (8)	0.0000 (8)

Br1—C4	1.899 (2)	C4—C5	1.372 (3)
O1—C1	1.361 (3)	C5—C6	1.402 (3)
O1—H1	0.812 (18)	C5—H5	0.9300
O8—C8	1.244 (3)	C6—C7	1.445 (3)
O11—C11	1.381 (3)	C7—H7	0.9300
O11—H11	0.827 (18)	C8—C9	1.487 (3)
O13—C13	1.361 (3)	C9—C14	1.389 (3)
O13—H13	0.785 (18)	C9—C10	1.398 (3)
N1—C7	1.279 (3)	C10—C11	1.375 (3)
N1—N2	1.379 (3)	C10—H10	0.9300
N2—C8	1.341 (3)	C11—C12	1.388 (3)
N2—H2N	0.851 (17)	C12—C13	1.386 (3)
C1—C2	1.383 (4)	C12—H12	0.9300
C1—C6	1.403 (3)	C13—C14	1.383 (3)
C2—C3	1.375 (4)	C14—H14	0.9300
C2—H2	0.9300	O2—H2A	0.807 (18)
C3—C4	1.389 (3)	O2—H2B	0.825 (18)
C3—H3	0.9300
C1—O1—H1	110 (2)	N1—C7—C6	121.5 (2)
C11—O11—H11	109 (2)	N1—C7—H7	119.2
C13—O13—H13	108 (3)	C6—C7—H7	119.2
C7—N1—N2	116.85 (18)	O8—C8—N2	121.5 (2)
C8—N2—N1	119.13 (18)	O8—C8—C9	121.2 (2)
C8—N2—H2N	125.0 (18)	N2—C8—C9	117.29 (18)
N1—N2—H2N	115.7 (18)	C14—C9—C10	120.3 (2)
O1—C1—C2	117.4 (2)	C14—C9—C8	117.02 (19)
O1—C1—C6	122.0 (2)	C10—C9—C8	122.7 (2)
C2—C1—C6	120.6 (2)	C11—C10—C9	118.6 (2)
C3—C2—C1	120.9 (2)	C11—C10—H10	120.7
C3—C2—H2	119.6	C9—C10—H10	120.7
C1—C2—H2	119.6	C10—C11—O11	122.1 (2)
C2—C3—C4	118.8 (2)	C10—C11—C12	121.8 (2)
C2—C3—H3	120.6	O11—C11—C12	116.1 (2)
C4—C3—H3	120.6	C13—C12—C11	118.9 (2)
C5—C4—C3	121.3 (2)	C13—C12—H12	120.5
C5—C4—Br1	119.64 (18)	C11—C12—H12	120.5
C3—C4—Br1	119.10 (19)	O13—C13—C14	122.5 (2)
C4—C5—C6	120.5 (2)	O13—C13—C12	117.0 (2)
C4—C5—H5	119.8	C14—C13—C12	120.4 (2)
C6—C5—H5	119.8	C13—C14—C9	119.91 (19)
C5—C6—C1	117.9 (2)	C13—C14—H14	120.0
C5—C6—C7	119.1 (2)	C9—C14—H14	120.0
C1—C6—C7	123.0 (2)	H2A—O2—H2B	105 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.81 (2)	1.95 (2)	2.657 (2)	145 (3)
N2—H2N···O2	0.85 (2)	2.07 (2)	2.913 (3)	170 (2)
O1—H1···O2i	0.81 (2)	2.52 (3)	2.942 (3)	114 (3)
O11—H11···O8ii	0.83 (2)	1.94 (2)	2.750 (2)	168 (3)
O13—H13···O1iii	0.79 (2)	2.19 (2)	2.959 (2)	165 (3)
O2—H2A···O8ii	0.81 (2)	1.98 (2)	2.776 (3)	171 (4)
O2—H2B···O11iv	0.83 (2)	2.06 (2)	2.861 (3)	165 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.81 (2)	1.95 (2)	2.657 (2)	145 (3)
N2—H2N⋯O2	0.85 (2)	2.07 (2)	2.913 (3)	170 (2)
O11—H11⋯O8i	0.83 (2)	1.94 (2)	2.750 (2)	168 (3)
O13—H13⋯O1ii	0.79 (2)	2.19 (2)	2.959 (2)	165 (3)
O2—H2A⋯O8i	0.81 (2)	1.98 (2)	2.776 (3)	171 (4)
O2—H2B⋯O11iii	0.83 (2)	2.06 (2)	2.861 (3)	165 (3)

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