(E)-4-Bromo-N'-(4-hy-droxy-3-meth-oxy-benzyl-idene)benzohydrazide monohydrate.

In the title compound, C(15)H(13)BrN(2)O(3)·H(2)O, the dihedral angle between the two benzene rings is 13.92 (6)°. The meth-oxy group of the 4-hy-droxy-3-meth-oxy-phenyl is almost coplanar with its bound benzene ring, as seen by the C(meth-yl)-O-C-C torsion angle of -0.35 (16)°. In the crystal, mol-ecules are linked into a three-dimensional network by N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds and also weak C-H⋯O inter-actions. A short C⋯O contact of 3.0191 (15) Å is also present.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Fun et al. (2011 ▶); Horkaew et al. (2011 ▶); Promdet et al. (2011 ▶). For background and applications of benzohydrazide derivatives, see: Loncle et al. (2004 ▶); Raj et al. (2007 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C15H13BrN2O3·H2O

M = 367.19

Monoclinic,

a = 7.9772 (7) Å

b = 21.446 (2) Å

c = 10.3928 (7) Å

β = 119.479 (5)°

V = 1547.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 2.68 mm−1

T = 100 K

0.58 × 0.21 × 0.11 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.306, T max = 0.756

18815 measured reflections

5602 independent reflections

4894 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.065

S = 1.04

5602 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.54 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201032X/fj2521sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201032X/fj2521Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201032X/fj2521Isup3.cml

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

C15H13BrN2O3·H2O	F(000) = 744
Mr = 367.19	Dx = 1.576 Mg m−3
Monoclinic, P21/c	Melting point > 513 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.9772 (7) Å	Cell parameters from 5602 reflections
b = 21.446 (2) Å	θ = 2.4–32.6°
c = 10.3928 (7) Å	µ = 2.68 mm−1
β = 119.479 (5)°	T = 100 K
V = 1547.8 (2) Å3	Block, colorless
Z = 4	0.58 × 0.21 × 0.11 mm

Bruker APEX DUO CCD area-detector diffractometer	5602 independent reflections
Radiation source: sealed tube	4894 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 32.6°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→12
Tmin = 0.306, Tmax = 0.756	k = −29→32
18815 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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0304P)2 + 0.5617P] where P = (Fo2 + 2Fc2)/3
5602 reflections	(Δ/σ)max = 0.009
200 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.54 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	1.165101 (18)	1.138681 (6)	1.032760 (13)	0.02180 (4)
O1	0.31020 (12)	0.98324 (4)	0.62686 (11)	0.02206 (18)
O2	−0.26566 (11)	0.74388 (4)	0.19684 (10)	0.01696 (15)
O3	−0.14414 (12)	0.64604 (4)	0.11703 (10)	0.01614 (15)
H1O3	−0.1053	0.6238	0.0752	0.024*
N1	0.50431 (13)	0.91557 (4)	0.59638 (11)	0.01464 (16)
H1N1	0.6171	0.9016	0.6218	0.018*
N2	0.34933 (13)	0.87658 (4)	0.51278 (11)	0.01445 (16)
C1	0.64474 (16)	1.00888 (5)	0.74049 (12)	0.01489 (18)
C2	0.62537 (18)	1.05722 (6)	0.82220 (15)	0.0223 (2)
H2A	0.5052	1.0635	0.8185	0.027*
C3	0.77907 (19)	1.09623 (6)	0.90869 (15)	0.0233 (2)
H3A	0.7652	1.1289	0.9644	0.028*
C4	0.95314 (17)	1.08667 (5)	0.91237 (13)	0.0176 (2)
C5	0.97598 (17)	1.03960 (6)	0.83136 (13)	0.0186 (2)
H5A	1.0960	1.0339	0.8344	0.022*
C6	0.82108 (17)	1.00077 (5)	0.74535 (13)	0.0178 (2)
H6A	0.8356	0.9684	0.6893	0.021*
C7	0.47302 (16)	0.96867 (5)	0.65048 (12)	0.01518 (19)
C8	0.39443 (15)	0.82791 (5)	0.46425 (12)	0.01448 (18)
H8A	0.5240	0.8228	0.4859	0.017*
C9	0.25378 (15)	0.78044 (5)	0.37726 (12)	0.01375 (18)
C10	0.05771 (15)	0.78701 (5)	0.33432 (12)	0.01418 (18)
H10A	0.0146	0.8225	0.3646	0.017*
C11	−0.07205 (15)	0.74162 (5)	0.24783 (12)	0.01331 (18)
C12	−0.00870 (15)	0.68869 (5)	0.20363 (12)	0.01369 (18)
C13	0.18522 (16)	0.68186 (5)	0.24792 (13)	0.01568 (19)
H13A	0.2288	0.6460	0.2194	0.019*
C14	0.31573 (16)	0.72779 (5)	0.33436 (13)	0.01619 (19)
H14A	0.4484	0.7231	0.3643	0.019*
C15	−0.33607 (17)	0.79716 (6)	0.23765 (15)	0.0201 (2)
H15A	−0.4763	0.7943	0.1930	0.030*
H15B	−0.3026	0.8350	0.2024	0.030*
H15C	−0.2776	0.7988	0.3455	0.030*
O1W	0.94692 (12)	0.92018 (4)	0.45250 (10)	0.01886 (16)
H1OW	0.8746	0.9503	0.4230	0.028*
H2OW	1.0559	0.9287	0.4881	0.028*

	U11	U22	U33	U12	U13	U23
Br1	0.02481 (7)	0.01815 (6)	0.01611 (6)	−0.00733 (4)	0.00520 (5)	−0.00200 (4)
O1	0.0137 (4)	0.0200 (4)	0.0292 (5)	0.0032 (3)	0.0080 (3)	−0.0033 (3)
O2	0.0091 (3)	0.0177 (4)	0.0223 (4)	−0.0001 (3)	0.0064 (3)	−0.0044 (3)
O3	0.0129 (3)	0.0161 (4)	0.0196 (4)	−0.0031 (3)	0.0081 (3)	−0.0051 (3)
N1	0.0099 (4)	0.0142 (4)	0.0170 (4)	−0.0005 (3)	0.0045 (3)	−0.0019 (3)
N2	0.0109 (4)	0.0147 (4)	0.0146 (4)	−0.0018 (3)	0.0039 (3)	−0.0008 (3)
C1	0.0152 (5)	0.0122 (4)	0.0150 (4)	0.0006 (3)	0.0056 (4)	0.0007 (3)
C2	0.0182 (5)	0.0206 (5)	0.0256 (6)	0.0023 (4)	0.0088 (5)	−0.0057 (4)
C3	0.0222 (6)	0.0194 (5)	0.0238 (6)	0.0011 (4)	0.0080 (5)	−0.0064 (4)
C4	0.0199 (5)	0.0145 (5)	0.0138 (5)	−0.0031 (4)	0.0046 (4)	−0.0002 (4)
C5	0.0184 (5)	0.0189 (5)	0.0194 (5)	−0.0048 (4)	0.0100 (4)	−0.0032 (4)
C6	0.0186 (5)	0.0166 (5)	0.0192 (5)	−0.0034 (4)	0.0101 (4)	−0.0039 (4)
C7	0.0137 (4)	0.0141 (4)	0.0154 (5)	0.0013 (3)	0.0053 (4)	0.0007 (4)
C8	0.0106 (4)	0.0154 (4)	0.0152 (5)	0.0000 (3)	0.0046 (4)	0.0007 (4)
C9	0.0112 (4)	0.0141 (4)	0.0145 (4)	−0.0005 (3)	0.0052 (4)	−0.0001 (3)
C10	0.0121 (4)	0.0143 (4)	0.0150 (5)	0.0001 (3)	0.0058 (4)	−0.0007 (4)
C11	0.0100 (4)	0.0147 (4)	0.0145 (4)	0.0003 (3)	0.0054 (4)	0.0006 (3)
C12	0.0116 (4)	0.0141 (4)	0.0142 (4)	−0.0015 (3)	0.0055 (4)	−0.0009 (3)
C13	0.0131 (4)	0.0148 (4)	0.0192 (5)	0.0006 (4)	0.0080 (4)	−0.0020 (4)
C14	0.0109 (4)	0.0172 (5)	0.0198 (5)	−0.0002 (4)	0.0070 (4)	−0.0013 (4)
C15	0.0134 (5)	0.0214 (5)	0.0261 (6)	0.0014 (4)	0.0103 (4)	−0.0048 (4)
O1W	0.0147 (4)	0.0161 (4)	0.0266 (4)	0.0023 (3)	0.0108 (3)	0.0042 (3)

Br1—C4	1.8939 (12)	C5—H5A	0.9500
O1—C7	1.2374 (14)	C6—H6A	0.9500
O2—C11	1.3650 (13)	C8—C9	1.4541 (15)
O2—C15	1.4266 (14)	C8—H8A	0.9500
O3—C12	1.3627 (13)	C9—C14	1.3911 (15)
O3—H1O3	0.8032	C9—C10	1.4066 (15)
N1—C7	1.3467 (14)	C10—C11	1.3825 (15)
N1—N2	1.3876 (13)	C10—H10A	0.9500
N1—H1N1	0.8572	C11—C12	1.4082 (15)
N2—C8	1.2853 (14)	C12—C13	1.3876 (15)
C1—C6	1.3935 (16)	C13—C14	1.3930 (16)
C1—C2	1.3959 (16)	C13—H13A	0.9500
C1—C7	1.4947 (16)	C14—H14A	0.9500
C2—C3	1.3879 (18)	C15—H15A	0.9800
C2—H2A	0.9500	C15—H15B	0.9800
C3—C4	1.3854 (18)	C15—H15C	0.9800
C3—H3A	0.9500	O1W—H1OW	0.8179
C4—C5	1.3828 (16)	O1W—H2OW	0.7806
C5—C6	1.3900 (16)
C11—O2—C15	116.68 (9)	N2—C8—H8A	118.9
C12—O3—H1O3	111.4	C9—C8—H8A	118.9
C7—N1—N2	118.68 (9)	C14—C9—C10	119.65 (10)
C7—N1—H1N1	123.2	C14—C9—C8	118.72 (9)
N2—N1—H1N1	117.4	C10—C9—C8	121.63 (10)
C8—N2—N1	113.57 (9)	C11—C10—C9	119.71 (10)
C6—C1—C2	118.85 (11)	C11—C10—H10A	120.1
C6—C1—C7	123.27 (10)	C9—C10—H10A	120.1
C2—C1—C7	117.87 (10)	O2—C11—C10	124.71 (10)
C3—C2—C1	120.97 (11)	O2—C11—C12	114.91 (9)
C3—C2—H2A	119.5	C10—C11—C12	120.37 (9)
C1—C2—H2A	119.5	O3—C12—C13	122.71 (10)
C4—C3—C2	118.85 (11)	O3—C12—C11	117.47 (9)
C4—C3—H3A	120.6	C13—C12—C11	119.82 (10)
C2—C3—H3A	120.6	C12—C13—C14	119.78 (10)
C5—C4—C3	121.46 (11)	C12—C13—H13A	120.1
C5—C4—Br1	119.34 (9)	C14—C13—H13A	120.1
C3—C4—Br1	119.20 (9)	C9—C14—C13	120.66 (10)
C4—C5—C6	119.15 (11)	C9—C14—H14A	119.7
C4—C5—H5A	120.4	C13—C14—H14A	119.7
C6—C5—H5A	120.4	O2—C15—H15A	109.5
C5—C6—C1	120.70 (11)	O2—C15—H15B	109.5
C5—C6—H6A	119.6	H15A—C15—H15B	109.5
C1—C6—H6A	119.6	O2—C15—H15C	109.5
O1—C7—N1	121.53 (10)	H15A—C15—H15C	109.5
O1—C7—C1	121.85 (10)	H15B—C15—H15C	109.5
N1—C7—C1	116.62 (9)	H1OW—O1W—H2OW	114.1
N2—C8—C9	122.22 (10)
C7—N1—N2—C8	178.70 (10)	N2—C8—C9—C14	−177.20 (11)
C6—C1—C2—C3	−0.88 (19)	N2—C8—C9—C10	3.67 (17)
C7—C1—C2—C3	179.75 (12)	C14—C9—C10—C11	−1.09 (16)
C1—C2—C3—C4	0.3 (2)	C8—C9—C10—C11	178.04 (10)
C2—C3—C4—C5	0.4 (2)	C15—O2—C11—C10	−0.35 (16)
C2—C3—C4—Br1	−178.89 (10)	C15—O2—C11—C12	−179.25 (10)
C3—C4—C5—C6	−0.52 (19)	C9—C10—C11—O2	−178.33 (10)
Br1—C4—C5—C6	178.78 (9)	C9—C10—C11—C12	0.52 (16)
C4—C5—C6—C1	−0.09 (18)	O2—C11—C12—O3	−0.29 (14)
C2—C1—C6—C5	0.77 (18)	C10—C11—C12—O3	−179.25 (10)
C7—C1—C6—C5	−179.89 (11)	O2—C11—C12—C13	179.38 (10)
N2—N1—C7—O1	−0.21 (17)	C10—C11—C12—C13	0.42 (16)
N2—N1—C7—C1	179.66 (9)	O3—C12—C13—C14	178.87 (10)
C6—C1—C7—O1	−166.86 (12)	C11—C12—C13—C14	−0.78 (17)
C2—C1—C7—O1	12.48 (17)	C10—C9—C14—C13	0.74 (17)
C6—C1—C7—N1	13.26 (16)	C8—C9—C14—C13	−178.42 (11)
C2—C1—C7—N1	−167.40 (11)	C12—C13—C14—C9	0.20 (18)
N1—N2—C8—C9	178.54 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···O1Wi	0.80	1.79	2.5867 (14)	170
N1—H1N1···O3ii	0.86	2.18	3.0107 (16)	162
O1W—H1OW···O1iii	0.82	1.93	2.7409 (14)	171
O1W—H2OW···O1iv	0.78	2.16	2.8883 (14)	154
O1W—H2OW···N2iv	0.78	2.49	3.0971 (16)	136
C6—H6A···O3ii	0.95	2.59	3.4832 (15)	156
C8—H8A···O2ii	0.95	2.46	3.0191 (15)	118
C8—H8A···O3ii	0.95	2.40	3.2604 (17)	150
C10—H10A···O1Wv	0.95	2.45	3.3933 (15)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯O1Wi	0.80	1.79	2.5867 (14)	170
N1—H1N1⋯O3ii	0.86	2.18	3.0107 (16)	162
O1W—H1OW⋯O1iii	0.82	1.93	2.7409 (14)	171
O1W—H2OW⋯O1iv	0.78	2.16	2.8883 (14)	154
O1W—H2OW⋯N2iv	0.78	2.49	3.0971 (16)	136
C6—H6A⋯O3ii	0.95	2.59	3.4832 (15)	156
C8—H8A⋯O3ii	0.95	2.40	3.2604 (17)	150
C10—H10A⋯O1Wv	0.95	2.45	3.3933 (15)	172

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