N'-[(E)-5-Bromo-2-hy-droxy-3-meth-oxy-benzyl-idene]benzohydrazide monohydrate.

The title compound, C15H13BrN2O3·H2O, exists in an E conformation with respect to the azo-methane C=N double bond. The benzene and phenyl rings form dihedral angles of 0.46 (2) and 4.90 (3)°, respectively with the central C(=O)N2C unit. An intra-molecular O-H⋯N hydrogen bond occurs. In the crystal, some hydrazide mol-ecules are replaced by mol-ecules of the 6-bromo isomer. The Br atom from this admixture was refined to give a partial occupancy of 0.0443 (19). A supra-molecular network is built in the lattice by means of inter-molecular N-H⋯O and two O-H⋯O inter-actions together with non-classical C-H⋯O inter-actions involving the lattice water mol-ecule stacking the mol-ecules along the b-axis direction.

Related literature

For biological applications of benzohydrazones and derivatives, see: Sreeja et al. (2004 ▶); Rada & Leto (2008 ▶); Rakha et al. (1996 ▶); Takahama (1996 ▶). For the synthesis of related compounds, see: Emmanuel et al. (2011 ▶). For a related structure, see Reshma et al. (2012 ▶).

Experimental

Crystal data

C15H13BrN2O3·H2O

M = 367.20

Orthorhombic,

a = 4.7223 (5) Å

b = 13.9357 (17) Å

c = 23.028 (3) Å

V = 1515.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.73 mm−1

T = 293 K

0.32 × 0.25 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.446, T max = 0.549

12759 measured reflections

2966 independent reflections

2189 reflections with I > 2σ(I)

R int = 0.090

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.114

S = 0.89

2966 reflections

218 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.29 e Å−3

Absolute structure: Flack (1983 ▶), 1203 Friedel pairs

Absolute structure parameter: 0.016 (16)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) Global, I. DOI: 10.1107/S1600536813030572/hg5359sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813030572/hg5359Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813030572/hg5359Isup3.cml

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

C15H13BrN2O3·H2O	F(000) = 744
Mr = 367.20	Dx = 1.609 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3233 reflections
a = 4.7223 (5) Å	θ = 2.3–28.0°
b = 13.9357 (17) Å	µ = 2.73 mm−1
c = 23.028 (3) Å	T = 293 K
V = 1515.4 (3) Å3	Block, pale brown
Z = 4	0.32 × 0.25 × 0.22 mm

Bruker Kappa APEXII CCD diffractometer	2966 independent reflections
Radiation source: fine-focus sealed tube	2189 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.090
Detector resolution: 8.33 pixels mm-1	θmax = 26.0°, θmin = 2.9°
ω and φ scan	h = −5→5
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −17→17
Tmin = 0.446, Tmax = 0.549	l = −22→28
12759 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.114	w = 1/[σ2(Fo2) + (0.P)2 + 1.2809P] where P = (Fo2 + 2Fc2)/3
S = 0.89	(Δ/σ)max = 0.001
2966 reflections	Δρmax = 0.45 e Å−3
218 parameters	Δρmin = −0.29 e Å−3
7 restraints	Absolute structure: Flack (1983), 1203 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.016 (16)

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	Occ. (<1)
Br1	1.56048 (13)	0.50757 (4)	0.94230 (3)	0.0664 (2)	0.956 (2)
Br1B	1.181 (4)	0.4776 (7)	0.8289 (6)	0.087 (7)	0.044 (2)
O1	1.0006 (7)	0.8426 (2)	0.82729 (16)	0.0610 (10)
H1	0.906 (14)	0.8268 (14)	0.798 (3)	0.092*
O2	1.3713 (8)	0.8739 (2)	0.90679 (15)	0.0598 (9)
O3	0.4122 (11)	0.8432 (2)	0.70096 (17)	0.0800 (12)
N1	0.7166 (9)	0.7183 (4)	0.76351 (16)	0.0552 (11)
N2	0.5260 (8)	0.6904 (3)	0.72170 (16)	0.0536 (11)
H2	0.4997	0.6305	0.7146	0.064*
C2	1.1208 (10)	0.7645 (3)	0.85060 (19)	0.0479 (11)
C3	1.3235 (10)	0.7802 (3)	0.8941 (2)	0.0478 (11)
C4	1.4551 (10)	0.7037 (3)	0.92142 (19)	0.0467 (11)
H4	1.5857	0.7140	0.9510	0.056*
C5	1.3871 (10)	0.6112 (3)	0.9036 (2)	0.0496 (11)
H5	1.4744	0.5592	0.9214	0.060*	0.044 (2)
C6	1.1964 (11)	0.5953 (3)	0.8607 (2)	0.0527 (12)
H6	1.1570	0.5327	0.8492	0.063*	0.956 (2)
C1	1.0590 (11)	0.6710 (3)	0.83351 (19)	0.0479 (11)
C7	0.8523 (11)	0.6512 (4)	0.7890 (2)	0.0555 (13)
H7	0.8168	0.5879	0.7787	0.067*
C8	0.3806 (11)	0.7575 (3)	0.6918 (2)	0.0516 (12)
C9	0.1805 (10)	0.7211 (3)	0.64786 (18)	0.0419 (10)
C10	0.1193 (10)	0.6254 (3)	0.6384 (2)	0.0489 (12)
H10	0.2073	0.5787	0.6609	0.059*
C11	−0.0706 (12)	0.5983 (3)	0.5959 (2)	0.0587 (13)
H11	−0.1095	0.5336	0.5901	0.070*
C12	−0.2013 (12)	0.6656 (4)	0.5626 (2)	0.0595 (13)
H12	−0.3291	0.6470	0.5340	0.071*
C13	−0.1445 (12)	0.7607 (4)	0.5713 (2)	0.0603 (14)
H13	−0.2330	0.8068	0.5484	0.072*
C14	0.0435 (11)	0.7882 (3)	0.6138 (2)	0.0559 (12)
H14	0.0791	0.8531	0.6196	0.067*
C15	1.5878 (12)	0.8956 (3)	0.9469 (2)	0.0616 (13)
H15A	1.5379	0.8706	0.9844	0.092*
H15B	1.6109	0.9639	0.9494	0.092*
H15C	1.7621	0.8669	0.9343	0.092*
O1W	0.4629 (10)	0.9794 (2)	0.78591 (18)	0.0782 (11)
H1A	0.473 (15)	0.944 (4)	0.7555 (18)	0.117*
H1B	0.346 (12)	0.952 (5)	0.809 (2)	0.117*

	U11	U22	U33	U12	U13	U23
Br1	0.0768 (4)	0.0492 (3)	0.0733 (4)	0.0101 (3)	−0.0021 (3)	0.0056 (3)
Br1B	0.127 (13)	0.058 (8)	0.077 (10)	−0.019 (8)	0.028 (9)	0.004 (7)
O1	0.059 (3)	0.064 (2)	0.060 (2)	0.0015 (17)	−0.0188 (19)	0.0050 (17)
O2	0.064 (2)	0.0475 (18)	0.067 (2)	0.0032 (17)	−0.0247 (19)	−0.0072 (16)
O3	0.108 (3)	0.054 (2)	0.078 (3)	−0.020 (2)	−0.012 (3)	−0.0184 (19)
N1	0.048 (2)	0.081 (3)	0.037 (2)	−0.018 (2)	0.000 (2)	−0.010 (2)
N2	0.051 (3)	0.068 (2)	0.042 (2)	−0.012 (2)	−0.003 (2)	−0.009 (2)
C2	0.045 (3)	0.059 (3)	0.039 (2)	−0.003 (2)	−0.001 (2)	−0.002 (2)
C3	0.049 (3)	0.049 (3)	0.045 (3)	−0.003 (2)	−0.005 (2)	−0.005 (2)
C4	0.044 (2)	0.055 (2)	0.041 (2)	0.002 (2)	−0.001 (2)	−0.005 (2)
C5	0.050 (3)	0.052 (3)	0.046 (3)	0.000 (2)	0.005 (2)	−0.001 (2)
C6	0.056 (3)	0.052 (3)	0.050 (3)	−0.006 (2)	0.004 (3)	−0.004 (2)
C1	0.044 (2)	0.063 (3)	0.036 (2)	−0.008 (3)	0.004 (2)	−0.009 (2)
C7	0.049 (3)	0.076 (3)	0.042 (3)	−0.015 (3)	0.004 (2)	−0.010 (3)
C8	0.054 (3)	0.057 (3)	0.044 (3)	−0.007 (3)	0.006 (2)	−0.008 (2)
C9	0.043 (2)	0.044 (2)	0.039 (2)	−0.002 (2)	0.007 (2)	−0.007 (2)
C10	0.053 (3)	0.042 (2)	0.052 (3)	0.001 (2)	−0.010 (2)	−0.002 (2)
C11	0.062 (3)	0.047 (3)	0.067 (3)	0.003 (3)	−0.013 (3)	−0.015 (2)
C12	0.057 (3)	0.069 (3)	0.052 (3)	0.006 (3)	−0.009 (3)	−0.005 (3)
C13	0.061 (3)	0.063 (3)	0.057 (3)	0.008 (3)	−0.006 (3)	0.011 (3)
C14	0.063 (3)	0.043 (2)	0.061 (3)	−0.002 (3)	0.005 (3)	0.000 (2)
C15	0.061 (3)	0.059 (3)	0.065 (3)	−0.002 (3)	−0.017 (3)	−0.011 (3)
O1W	0.111 (3)	0.053 (2)	0.071 (2)	−0.012 (2)	−0.018 (2)	−0.0054 (18)

Br1—C5	1.885 (5)	C1—C7	1.441 (7)
Br1B—C6	1.798 (8)	C7—H7	0.9300
O1—C2	1.339 (6)	C8—C9	1.475 (6)
O1—H1	0.8311	C9—C14	1.382 (6)
O2—C3	1.357 (5)	C9—C10	1.382 (6)
O2—C15	1.411 (6)	C10—C11	1.379 (7)
O3—C8	1.221 (5)	C10—H10	0.9300
N1—C7	1.277 (7)	C11—C12	1.360 (7)
N1—N2	1.374 (5)	C11—H11	0.9300
N2—C8	1.349 (6)	C12—C13	1.366 (7)
N2—H2	0.8600	C12—H12	0.9300
C2—C1	1.392 (6)	C13—C14	1.376 (7)
C2—C3	1.403 (6)	C13—H13	0.9300
C3—C4	1.385 (6)	C14—H14	0.9300
C4—C5	1.391 (6)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.355 (7)	C15—H15C	0.9600
C5—H5	0.9300	O1W—H1A	0.86 (2)
C6—C1	1.387 (6)	O1W—H1B	0.86 (2)
C6—H6	0.9300
C2—O1—H1	109.5	C1—C7—H7	119.1
C3—O2—C15	117.9 (4)	O3—C8—N2	121.9 (5)
C7—N1—N2	116.3 (5)	O3—C8—C9	122.2 (5)
C8—N2—N1	119.6 (4)	N2—C8—C9	116.0 (4)
C8—N2—H2	120.2	C14—C9—C10	117.7 (4)
N1—N2—H2	120.2	C14—C9—C8	117.2 (4)
O1—C2—C1	123.9 (4)	C10—C9—C8	125.1 (4)
O1—C2—C3	116.7 (4)	C11—C10—C9	120.8 (4)
C1—C2—C3	119.4 (4)	C11—C10—H10	119.6
O2—C3—C4	124.6 (4)	C9—C10—H10	119.6
O2—C3—C2	114.6 (4)	C12—C11—C10	120.4 (4)
C4—C3—C2	120.7 (4)	C12—C11—H11	119.8
C3—C4—C5	118.4 (4)	C10—C11—H11	119.8
C3—C4—H4	120.8	C11—C12—C13	119.8 (5)
C5—C4—H4	120.8	C11—C12—H12	120.1
C6—C5—C4	121.4 (4)	C13—C12—H12	120.1
C6—C5—Br1	120.6 (4)	C12—C13—C14	120.1 (5)
C4—C5—Br1	118.0 (4)	C12—C13—H13	120.0
C6—C5—H5	119.3	C14—C13—H13	120.0
C4—C5—H5	119.3	C9—C14—C13	121.2 (4)
C5—C6—C1	121.0 (4)	C9—C14—H14	119.4
C5—C6—Br1B	118.3 (7)	C13—C14—H14	119.4
C1—C6—Br1B	119.4 (7)	O2—C15—H15A	109.5
C5—C6—H6	119.5	O2—C15—H15B	109.5
C1—C6—H6	119.5	H15A—C15—H15B	109.5
C6—C1—C2	119.1 (4)	O2—C15—H15C	109.5
C6—C1—C7	119.4 (5)	H15A—C15—H15C	109.5
C2—C1—C7	121.5 (5)	H15B—C15—H15C	109.5
N1—C7—C1	121.8 (5)	H1A—O1W—H1B	106 (4)
N1—C7—H7	119.1
C7—N1—N2—C8	−178.2 (4)	C3—C2—C1—C6	1.1 (7)
C15—O2—C3—C4	5.9 (7)	O1—C2—C1—C7	−1.1 (7)
C15—O2—C3—C2	−175.2 (4)	C3—C2—C1—C7	180.0 (4)
O1—C2—C3—O2	−0.1 (6)	N2—N1—C7—C1	179.7 (4)
C1—C2—C3—O2	178.9 (4)	C6—C1—C7—N1	178.7 (5)
O1—C2—C3—C4	178.8 (4)	C2—C1—C7—N1	−0.2 (7)
C1—C2—C3—C4	−2.2 (7)	N1—N2—C8—O3	−0.3 (7)
O2—C3—C4—C5	−179.5 (5)	N1—N2—C8—C9	−179.9 (4)
C2—C3—C4—C5	1.8 (7)	O3—C8—C9—C14	4.8 (7)
C3—C4—C5—C6	−0.2 (7)	N2—C8—C9—C14	−175.5 (4)
C3—C4—C5—Br1	−178.5 (4)	O3—C8—C9—C10	−175.0 (5)
C4—C5—C6—C1	−0.9 (7)	N2—C8—C9—C10	4.7 (7)
Br1—C5—C6—C1	177.3 (4)	C14—C9—C10—C11	0.5 (7)
C4—C5—C6—Br1B	165.9 (7)	C8—C9—C10—C11	−179.7 (5)
Br1—C5—C6—Br1B	−15.9 (8)	C9—C10—C11—C12	0.0 (8)
C5—C6—C1—C2	0.5 (7)	C10—C11—C12—C13	−0.1 (9)
Br1B—C6—C1—C2	−166.1 (7)	C11—C12—C13—C14	−0.3 (9)
C5—C6—C1—C7	−178.5 (4)	C10—C9—C14—C13	−0.8 (7)
Br1B—C6—C1—C7	14.9 (9)	C8—C9—C14—C13	179.4 (5)
O1—C2—C1—C6	−180.0 (4)	C12—C13—C14—C9	0.8 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1Wi	0.86	2.11	2.946 (5)	163
O1—H1···N1	0.83	1.93	2.637 (5)	142
O1W—H1B···O2ii	0.86 (2)	2.50 (5)	3.178 (5)	136 (6)
O1W—H1B···O1ii	0.86 (2)	2.27 (4)	3.051 (5)	151 (6)
O1W—H1A···O3	0.86 (2)	1.91 (3)	2.736 (5)	163 (6)
C7—H7···O1Wi	0.93	2.50	3.305 (6)	145
C10—H10···O1Wi	0.93	2.42	3.329 (6)	166
C11—H11···O2i	0.93	2.55	3.435 (5)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1W i	0.86	2.11	2.946 (5)	163
O1—H1⋯N1	0.83	1.93	2.637 (5)	142
O1W—H1B⋯O2ii	0.86 (2)	2.50 (5)	3.178 (5)	136 (6)
O1W—H1B⋯O1ii	0.86 (2)	2.27 (4)	3.051 (5)	151 (6)
O1W—H1A⋯O3	0.86 (2)	1.91 (3)	2.736 (5)	163 (6)
C7—H7⋯O1W i	0.93	2.50	3.305 (6)	145
C10—H10⋯O1W i	0.93	2.42	3.329 (6)	166
C11—H11⋯O2i	0.93	2.55	3.435 (5)	160

Symmetry codes: (i) ; (ii) .