(E)-4-Amino-N'-(5-bromo-2-hy-droxy-benzyl-idene)benzohydrazide mono-hydrate.

In t the title compound, C(14)H(12)BrN(3)O(2). H(2)O, the conformation of the C=N double bond in the hydrazide Schiff base mol-ecule is E. The dihedral angle between the benzene rings is 48.01 (11) °. An intra-molecular O-H⋯N hydrogen bond makes an S(6) ring motif. In the crystal, mol-ecules are linked through N-H⋯O (bifurcated acceptor) and O-H⋯O hydrogen bonds, forming two-dimensional networks lying parallel to (100).

Related literature

For the coordination chemistry of Schiff base and hydrazone derivatives, see: Kucukguzel et al. (2006 ▶); Karthikeyan et al. (2006 ▶). For 4-amino­benzohydrazide-derived Schiff base structures, see: Xu (2012 ▶); Shi & Li (2012 ▶); Bakir & Green (2002 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H12BrN3O2·H2O

M = 352.19

Monoclinic,

a = 15.8435 (11) Å

b = 7.1718 (6) Å

c = 12.6462 (8) Å

β = 101.391 (3)°

V = 1408.64 (18) Å3

Z = 4

Mo Kα radiation

μ = 2.93 mm−1

T = 291 K

0.32 × 0.26 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.454, T max = 0.565

11798 measured reflections

3138 independent reflections

2543 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.077

S = 1.04

3138 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.49 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812025950/su2450sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025950/su2450Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812025950/su2450Isup3.cml

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

C14H12BrN3O2·H2O	F(000) = 712
Mr = 352.19	Dx = 1.661 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2225 reflections
a = 15.8435 (11) Å	θ = 2.5–27.5°
b = 7.1718 (6) Å	µ = 2.93 mm−1
c = 12.6462 (8) Å	T = 291 K
β = 101.391 (3)°	Prism, white
V = 1408.64 (18) Å3	0.32 × 0.26 × 0.22 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3138 independent reflections
Radiation source: fine-focus sealed tube	2543 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 27.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −20→20
Tmin = 0.454, Tmax = 0.565	k = −9→8
11798 measured reflections	l = −9→16

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0361P)2 + 0.4505P] where P = (Fo2 + 2Fc2)/3
3138 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.49 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	−0.256908 (14)	0.19559 (3)	0.351278 (19)	0.04528 (10)
O1	0.27754 (10)	0.3064 (2)	0.77430 (12)	0.0463 (4)
O2	0.02746 (10)	0.1315 (3)	0.74256 (12)	0.0490 (4)
H2O	0.0786	0.1768	0.7273	0.073*
O1W	0.20712 (12)	0.0602 (3)	0.88744 (12)	0.0555 (5)
H1W1	0.1801	−0.0294	0.8452	0.083*
H2W1	0.2246	0.1388	0.8402	0.083*
N1	0.61249 (13)	0.3236 (4)	0.5692 (2)	0.0675 (7)
H1N1	0.6101	0.3120	0.4985	0.081*
H2N1	0.6429	0.4174	0.6041	0.081*
N2	0.21269 (10)	0.3032 (2)	0.59806 (14)	0.0322 (4)
H2N	0.2133	0.3342	0.5294	0.039*
N3	0.13313 (11)	0.2630 (2)	0.62093 (15)	0.0321 (4)
C1	0.36621 (12)	0.3254 (3)	0.64417 (16)	0.0297 (4)
C2	0.38195 (13)	0.2378 (3)	0.55174 (17)	0.0344 (5)
H2	0.3372	0.1774	0.5059	0.041*
C3	0.46277 (15)	0.2394 (3)	0.5272 (2)	0.0425 (5)
H3	0.4721	0.1783	0.4657	0.051*
C4	0.53040 (14)	0.3309 (3)	0.5931 (2)	0.0428 (6)
C5	0.51473 (13)	0.4213 (4)	0.6841 (2)	0.0475 (6)
H5	0.5592	0.4855	0.7283	0.057*
C6	0.43430 (13)	0.4174 (3)	0.70993 (17)	0.0384 (5)
H6	0.4254	0.4771	0.7721	0.046*
C7	0.28256 (13)	0.3116 (3)	0.67866 (16)	0.0304 (4)
C8	0.06943 (13)	0.2690 (3)	0.54186 (17)	0.0321 (4)
H7	0.0781	0.3071	0.4745	0.039*
C9	−0.01679 (12)	0.2173 (3)	0.55511 (16)	0.0284 (4)
C10	−0.03425 (13)	0.1483 (3)	0.65254 (17)	0.0328 (4)
C11	−0.11712 (13)	0.0932 (3)	0.65825 (17)	0.0369 (5)
H11	−0.1282	0.0459	0.7226	0.044*
C12	−0.18330 (12)	0.1076 (3)	0.56950 (17)	0.0352 (5)
H12	−0.2389	0.0715	0.5740	0.042*
C13	−0.16619 (12)	0.1761 (3)	0.47410 (17)	0.0317 (4)
C14	−0.08416 (13)	0.2293 (3)	0.46589 (17)	0.0304 (4)
H14	−0.0737	0.2735	0.4005	0.037*

	U11	U22	U33	U12	U13	U23
Br1	0.03422 (13)	0.04959 (16)	0.04628 (16)	−0.00074 (10)	−0.00607 (10)	−0.00069 (10)
O1	0.0456 (9)	0.0669 (12)	0.0280 (8)	−0.0112 (8)	0.0110 (7)	−0.0009 (7)
O2	0.0392 (8)	0.0719 (12)	0.0331 (8)	−0.0078 (8)	0.0005 (6)	0.0088 (8)
O1W	0.0755 (12)	0.0603 (12)	0.0319 (9)	−0.0168 (9)	0.0136 (8)	−0.0011 (8)
N1	0.0289 (10)	0.0796 (18)	0.0962 (19)	0.0066 (10)	0.0174 (11)	0.0289 (14)
N2	0.0246 (8)	0.0455 (11)	0.0279 (9)	−0.0050 (7)	0.0084 (7)	0.0004 (7)
N3	0.0251 (8)	0.0364 (9)	0.0369 (10)	−0.0046 (7)	0.0109 (7)	−0.0024 (7)
C1	0.0260 (9)	0.0326 (11)	0.0294 (10)	−0.0018 (8)	0.0029 (8)	0.0037 (8)
C2	0.0288 (10)	0.0368 (12)	0.0368 (12)	−0.0025 (8)	0.0047 (9)	−0.0015 (9)
C3	0.0394 (12)	0.0462 (13)	0.0447 (14)	0.0069 (10)	0.0156 (10)	0.0046 (10)
C4	0.0267 (10)	0.0430 (13)	0.0593 (15)	0.0052 (9)	0.0101 (10)	0.0219 (11)
C5	0.0277 (11)	0.0473 (14)	0.0599 (16)	−0.0101 (10)	−0.0096 (10)	0.0089 (12)
C6	0.0363 (11)	0.0407 (12)	0.0347 (12)	−0.0045 (9)	−0.0014 (9)	−0.0004 (9)
C7	0.0301 (10)	0.0335 (11)	0.0274 (10)	−0.0026 (8)	0.0049 (8)	0.0004 (8)
C8	0.0294 (10)	0.0361 (11)	0.0326 (11)	−0.0005 (8)	0.0104 (8)	−0.0012 (8)
C9	0.0259 (9)	0.0288 (10)	0.0317 (11)	−0.0011 (7)	0.0086 (8)	−0.0016 (8)
C10	0.0320 (10)	0.0372 (11)	0.0287 (10)	−0.0008 (8)	0.0051 (8)	−0.0008 (8)
C11	0.0362 (11)	0.0447 (13)	0.0327 (11)	−0.0062 (10)	0.0135 (9)	0.0005 (9)
C12	0.0267 (10)	0.0376 (12)	0.0427 (12)	−0.0050 (9)	0.0105 (8)	−0.0052 (10)
C13	0.0267 (9)	0.0319 (11)	0.0347 (11)	0.0006 (8)	0.0021 (8)	−0.0060 (8)
C14	0.0312 (10)	0.0318 (11)	0.0290 (11)	−0.0002 (8)	0.0077 (8)	−0.0003 (8)

Br1—C13	1.902 (2)	C3—C4	1.386 (4)
O1—C7	1.228 (2)	C3—H3	0.9300
O2—C10	1.352 (3)	C4—C5	1.384 (4)
O2—H2O	0.9276	C5—C6	1.377 (3)
O1W—H1W1	0.8893	C5—H5	0.9300
O1W—H2W1	0.9036	C6—H6	0.9300
N1—C4	1.393 (3)	C8—C9	1.457 (3)
N1—H1N1	0.8915	C8—H7	0.9300
N1—H2N1	0.8923	C9—C14	1.394 (3)
N2—C7	1.350 (3)	C9—C10	1.405 (3)
N2—N3	1.378 (2)	C10—C11	1.387 (3)
N2—H2N	0.8985	C11—C12	1.380 (3)
N3—C8	1.273 (3)	C11—H11	0.9300
C1—C6	1.392 (3)	C12—C13	1.378 (3)
C1—C2	1.392 (3)	C12—H12	0.9300
C1—C7	1.478 (3)	C13—C14	1.378 (3)
C2—C3	1.376 (3)	C14—H14	0.9300
C2—H2	0.9300
C10—O2—H2O	108.0	C1—C6—H6	119.6
H1W1—O1W—H2W1	103.2	O1—C7—N2	122.64 (19)
C4—N1—H1N1	111.3	O1—C7—C1	121.92 (19)
C4—N1—H2N1	107.5	N2—C7—C1	115.44 (18)
H1N1—N1—H2N1	118.5	N3—C8—C9	121.11 (19)
C7—N2—N3	119.90 (17)	N3—C8—H7	119.4
C7—N2—H2N	123.7	C9—C8—H7	119.4
N3—N2—H2N	116.1	C14—C9—C10	118.67 (18)
C8—N3—N2	116.35 (17)	C14—C9—C8	118.45 (18)
C6—C1—C2	118.00 (19)	C10—C9—C8	122.82 (18)
C6—C1—C7	119.32 (19)	O2—C10—C11	117.74 (19)
C2—C1—C7	122.52 (18)	O2—C10—C9	122.36 (18)
C3—C2—C1	121.0 (2)	C11—C10—C9	119.90 (19)
C3—C2—H2	119.5	C12—C11—C10	120.8 (2)
C1—C2—H2	119.5	C12—C11—H11	119.6
C2—C3—C4	120.8 (2)	C10—C11—H11	119.6
C2—C3—H3	119.6	C13—C12—C11	119.30 (18)
C4—C3—H3	119.6	C13—C12—H12	120.3
C5—C4—C3	118.5 (2)	C11—C12—H12	120.3
C5—C4—N1	121.8 (2)	C12—C13—C14	121.08 (19)
C3—C4—N1	119.7 (3)	C12—C13—Br1	119.59 (15)
C6—C5—C4	120.9 (2)	C14—C13—Br1	119.33 (16)
C6—C5—H5	119.5	C13—C14—C9	120.29 (19)
C4—C5—H5	119.5	C13—C14—H14	119.9
C5—C6—C1	120.8 (2)	C9—C14—H14	119.9
C5—C6—H6	119.6
C7—N2—N3—C8	175.72 (19)	N2—N3—C8—C9	175.98 (18)
C6—C1—C2—C3	1.2 (3)	N3—C8—C9—C14	179.08 (19)
C7—C1—C2—C3	−174.1 (2)	N3—C8—C9—C10	−3.7 (3)
C1—C2—C3—C4	−1.1 (3)	C14—C9—C10—O2	179.73 (19)
C2—C3—C4—C5	−0.2 (3)	C8—C9—C10—O2	2.5 (3)
C2—C3—C4—N1	177.1 (2)	C14—C9—C10—C11	0.3 (3)
C3—C4—C5—C6	1.3 (3)	C8—C9—C10—C11	−176.9 (2)
N1—C4—C5—C6	−176.0 (2)	O2—C10—C11—C12	179.6 (2)
C4—C5—C6—C1	−1.2 (4)	C9—C10—C11—C12	−0.9 (3)
C2—C1—C6—C5	−0.1 (3)	C10—C11—C12—C13	0.6 (3)
C7—C1—C6—C5	175.3 (2)	C11—C12—C13—C14	0.3 (3)
N3—N2—C7—O1	−8.8 (3)	C11—C12—C13—Br1	179.78 (16)
N3—N2—C7—C1	170.52 (17)	C12—C13—C14—C9	−0.9 (3)
C6—C1—C7—O1	−30.2 (3)	Br1—C13—C14—C9	179.60 (15)
C2—C1—C7—O1	145.0 (2)	C10—C9—C14—C13	0.6 (3)
C6—C1—C7—N2	150.5 (2)	C8—C9—C14—C13	177.93 (19)
C2—C1—C7—N2	−34.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···N3	0.93	1.84	2.660 (2)	145
N2—H2N···O1Wi	0.90	1.93	2.823 (2)	171
N1—H2N1···O1Wii	0.89	2.57	3.276 (3)	137
O1W—H2W1···O1	0.90	1.77	2.653 (2)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯N3	0.93	1.84	2.660 (2)	145
N2—H2N⋯O1W i	0.90	1.93	2.823 (2)	171
N1—H2N1⋯O1W ii	0.89	2.57	3.276 (3)	137
O1W—H2W1⋯O1	0.90	1.77	2.653 (2)	167

Symmetry codes: (i) ; (ii) .