N'-[(E)-5-Bromo-2-hy-droxy-3-meth-oxy-benzyl-idene]-4-meth-oxy-benzohydrazide monohydrate.

In the title compound, C(16)H(15)BrN(2)O(4)·H(2)O, the hydrazide mol-ecule is nearly planar, with a largest deviation from the mean plane through the non-H atoms of 0.106 (4) Å and a dihedral angle between the benzene rings of 1.98 (16)°. This mol-ecule adopts an E conformation about the C=N bond and an intra-molecular O-H⋯N hydrogen bond increases the rigidity. In the crystal, some mol-ecules of the title hydrazide are replaced by mol-ecules of its 6-bromo isomer, and the Br atom from this admixture mol-ecule was refined to give a partial occupancy of 0.0523 (13). The hydrazide and water mol-ecules are linked through classical N-H⋯O and O-H⋯O hydrogen bonds, forming layers parallel to (110). C-H⋯π inter-actions are also present.

Related literature

For the biological activity of hydrazone compounds, see: Metwally et al. (2006 ▶); Cukurovali et al. (2006 ▶). For the synthesis of related compounds, see: Emmanuel et al. (2011 ▶); Mangalam & Kurup (2011 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For related structures, see: Tan (2012 ▶); Hou & Bi (2012 ▶); Shen et al. (2012 ▶).

Experimental

Crystal data

C16H15BrN2O4·n class="Chemical">H2O

M = 397.22

Monoclinic,

a = 4.9730 (4) Å

b = 13.5721 (12) Å

c = 24.907 (2) Å

β = 90.921 (4)°

V = 1680.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 2.47 mm−1

T = 296 K

0.40 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.414, T max = 0.539

12692 measured reflections

2939 independent reflections

2268 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.094

S = 1.06

2939 reflections

247 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.52 e Å−3

Δρmin = −0.34 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: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812033806/yk2067sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033806/yk2067Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033806/yk2067Isup3.cml

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

C16H15BrN2O4·H2O	F(000) = 808
Mr = 397.22	Dx = 1.570 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4929 reflections
a = 4.9730 (4) Å	θ = 2.9–25.6°
b = 13.5721 (12) Å	µ = 2.47 mm−1
c = 24.907 (2) Å	T = 296 K
β = 90.921 (4)°	Block, brown
V = 1680.8 (2) Å3	0.40 × 0.30 × 0.25 mm
Z = 4

Bruker Kappa APEXII CCD area-detector diffractometer	2939 independent reflections
Radiation source: fine-focus sealed tube	2268 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 8.33 pixels mm-1	θmax = 25.0°, θmin = 2.9°
ω and φ scan	h = −5→5
Absorption correction: multi-scan (SADABS; Bruker, 2007)	k = −16→16
Tmin = 0.414, Tmax = 0.539	l = −29→29
12692 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.043P)2 + 0.7865P] where P = (Fo2 + 2Fc2)/3
2939 reflections	(Δ/σ)max < 0.001
247 parameters	Δρmax = 0.52 e Å−3
6 restraints	Δρmin = −0.34 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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)
O1W	0.6146 (7)	0.53984 (18)	0.20575 (11)	0.0857 (8)
H1W	0.479 (6)	0.521 (3)	0.1873 (16)	0.129*
H2W	0.651 (9)	0.496 (2)	0.2293 (14)	0.129*
Br1A	0.86593 (7)	0.06757 (2)	0.072139 (15)	0.06810 (16)	0.9477 (13)
H1A	0.476 (8)	0.0862 (12)	0.1601 (13)	0.058 (11)*	0.9477 (13)
Br1B	0.5677 (14)	0.0463 (4)	0.1799 (3)	0.064 (3)	0.0523 (13)
H1B	0.7630	0.1200	0.0880	0.058 (11)*	0.0523 (13)
O1	0.5501 (5)	0.43453 (15)	0.08852 (9)	0.0653 (6)
O2	0.2111 (4)	0.39584 (17)	0.16439 (9)	0.0629 (6)
O3	−0.2919 (5)	0.39947 (18)	0.27910 (10)	0.0789 (7)
O4	−1.0445 (4)	0.21328 (16)	0.45317 (8)	0.0616 (6)
N1	0.0049 (5)	0.2680 (2)	0.22932 (9)	0.0554 (6)
N2	−0.1688 (5)	0.2415 (2)	0.26906 (9)	0.0528 (6)
C1	0.4937 (6)	0.1490 (2)	0.14527 (12)	0.0534 (7)
C2	0.6652 (6)	0.1699 (2)	0.10475 (11)	0.0502 (7)
C3	0.6936 (6)	0.2646 (2)	0.08475 (11)	0.0514 (7)
H3	0.8149	0.2775	0.0576	0.062*
C4	0.5407 (6)	0.3389 (2)	0.10554 (11)	0.0489 (7)
C5	0.3586 (5)	0.3192 (2)	0.14656 (11)	0.0478 (7)
C6	0.3366 (6)	0.2237 (2)	0.16659 (11)	0.0492 (7)
C7	0.1512 (6)	0.1998 (2)	0.20906 (11)	0.0559 (7)
H7	0.1382	0.1354	0.2216	0.067*
C8	−0.3172 (6)	0.3134 (2)	0.29184 (11)	0.0511 (7)
C9	−0.5107 (5)	0.2833 (2)	0.33332 (10)	0.0444 (6)
C10	−0.6695 (6)	0.3560 (2)	0.35495 (12)	0.0514 (7)
H10	−0.6532	0.4202	0.3424	0.062*
C11	−0.8522 (6)	0.3363 (2)	0.39472 (12)	0.0514 (7)
H11	−0.9568	0.3866	0.4088	0.062*
C12	−0.8775 (5)	0.2411 (2)	0.41334 (11)	0.0459 (7)
C13	−0.7265 (6)	0.1670 (2)	0.39097 (12)	0.0530 (7)
H13	−0.7489	0.1024	0.4025	0.064*
C14	−0.5433 (6)	0.1873 (2)	0.35177 (12)	0.0515 (7)
H14	−0.4406	0.1367	0.3375	0.062*
C15	0.7560 (7)	0.4612 (2)	0.05349 (14)	0.0685 (9)
H15A	0.9270	0.4437	0.0692	0.103*
H15B	0.7503	0.5310	0.0473	0.103*
H15C	0.7317	0.4272	0.0200	0.103*
C16	−1.2105 (6)	0.2868 (3)	0.47648 (13)	0.0702 (9)
H16A	−1.0998	0.3387	0.4908	0.105*
H16B	−1.3132	0.2581	0.5048	0.105*
H16C	−1.3305	0.3131	0.4495	0.105*
H21	−0.165 (7)	0.1796 (9)	0.2766 (13)	0.067 (10)*
H2	0.116 (8)	0.375 (4)	0.1910 (13)	0.130 (18)*

	U11	U22	U33	U12	U13	U23
O1W	0.122 (2)	0.0518 (14)	0.0830 (19)	−0.0127 (14)	−0.0071 (16)	0.0124 (12)
Br1A	0.0682 (2)	0.0490 (2)	0.0875 (3)	0.00715 (17)	0.01531 (18)	−0.00284 (18)
Br1B	0.080 (5)	0.040 (4)	0.072 (5)	−0.002 (3)	−0.010 (3)	0.004 (3)
O1	0.0735 (14)	0.0462 (12)	0.0770 (14)	0.0028 (10)	0.0238 (12)	0.0056 (11)
O2	0.0632 (14)	0.0619 (13)	0.0643 (14)	0.0019 (11)	0.0177 (11)	−0.0062 (11)
O3	0.0930 (18)	0.0588 (14)	0.0854 (17)	0.0022 (13)	0.0209 (14)	0.0284 (12)
O4	0.0562 (12)	0.0676 (14)	0.0615 (12)	0.0041 (11)	0.0159 (10)	0.0053 (11)
N1	0.0516 (14)	0.0730 (18)	0.0415 (13)	−0.0144 (13)	0.0024 (11)	0.0006 (12)
N2	0.0566 (15)	0.0569 (17)	0.0453 (13)	−0.0085 (13)	0.0100 (11)	0.0035 (12)
C1	0.0563 (18)	0.0503 (18)	0.0536 (17)	−0.0071 (15)	0.0001 (14)	0.0039 (15)
C2	0.0459 (16)	0.0512 (17)	0.0536 (17)	−0.0003 (13)	−0.0002 (13)	−0.0052 (14)
C3	0.0462 (16)	0.0546 (18)	0.0535 (17)	−0.0059 (14)	0.0074 (13)	−0.0012 (14)
C4	0.0508 (16)	0.0435 (16)	0.0526 (16)	−0.0040 (13)	0.0049 (13)	−0.0019 (13)
C5	0.0460 (15)	0.0545 (18)	0.0431 (15)	−0.0040 (13)	0.0025 (12)	−0.0071 (13)
C6	0.0466 (16)	0.0577 (18)	0.0434 (15)	−0.0107 (14)	−0.0012 (12)	−0.0007 (13)
C7	0.0575 (18)	0.0621 (19)	0.0481 (16)	−0.0116 (16)	0.0041 (14)	0.0027 (15)
C8	0.0568 (17)	0.0482 (18)	0.0483 (16)	−0.0048 (14)	−0.0034 (13)	0.0089 (14)
C9	0.0444 (15)	0.0444 (15)	0.0442 (15)	−0.0014 (12)	−0.0037 (12)	0.0050 (12)
C10	0.0540 (17)	0.0422 (16)	0.0579 (17)	0.0009 (13)	−0.0047 (14)	0.0044 (13)
C11	0.0476 (16)	0.0480 (17)	0.0586 (18)	0.0083 (13)	−0.0014 (14)	−0.0048 (14)
C12	0.0390 (14)	0.0509 (17)	0.0478 (15)	0.0006 (12)	−0.0022 (12)	0.0001 (13)
C13	0.0577 (17)	0.0416 (16)	0.0600 (18)	−0.0024 (13)	0.0070 (14)	0.0041 (13)
C14	0.0557 (17)	0.0428 (16)	0.0562 (17)	0.0023 (13)	0.0092 (14)	0.0008 (13)
C15	0.074 (2)	0.0533 (19)	0.079 (2)	−0.0056 (16)	0.0200 (18)	0.0094 (17)
C16	0.0533 (19)	0.093 (3)	0.065 (2)	0.0132 (18)	0.0134 (16)	−0.0010 (18)

O1W—H1W	0.85 (3)	C5—C6	1.394 (4)
O1W—H2W	0.86 (3)	C6—C7	1.451 (4)
Br1A—C2	1.901 (3)	C7—H7	0.9300
O1—C4	1.366 (3)	C8—C9	1.480 (4)
O1—C15	1.404 (4)	C9—C10	1.379 (4)
O2—C5	1.352 (3)	C9—C14	1.393 (4)
O2—H2	0.87 (3)	C10—C11	1.381 (4)
O3—C8	1.217 (3)	C10—H10	0.9300
O4—C12	1.357 (3)	C11—C12	1.379 (4)
O4—C16	1.425 (4)	C11—H11	0.9300
N1—C7	1.285 (4)	C12—C13	1.378 (4)
N1—N2	1.372 (3)	C13—C14	1.374 (4)
N2—C8	1.353 (4)	C13—H13	0.9300
N2—H21	0.861 (14)	C14—H14	0.9300
C1—C2	1.362 (4)	C15—H15A	0.9600
C1—C6	1.390 (4)	C15—H15B	0.9600
C1—H1A	0.93 (4)	C15—H15C	0.9600
C2—C3	1.386 (4)	C16—H16A	0.9600
C3—C4	1.370 (4)	C16—H16B	0.9600
C3—H3	0.9300	C16—H16C	0.9600
C4—C5	1.402 (4)
H1W—O1W—H2W	108 (2)	N2—C8—C9	117.3 (2)
C4—O1—C15	117.8 (2)	C10—C9—C14	118.0 (3)
C5—O2—H2	108 (3)	C10—C9—C8	117.3 (2)
C12—O4—C16	117.9 (2)	C14—C9—C8	124.7 (3)
C7—N1—N2	117.5 (3)	C9—C10—C11	122.0 (3)
C8—N2—N1	117.9 (3)	C9—C10—H10	119.0
C8—N2—H21	128 (2)	C11—C10—H10	119.0
N1—N2—H21	114 (2)	C12—C11—C10	119.2 (3)
C2—C1—C6	119.6 (3)	C12—C11—H11	120.4
C2—C1—H1A	123 (2)	C10—C11—H11	120.4
C6—C1—H1A	117 (2)	O4—C12—C13	115.9 (3)
C1—C2—C3	121.9 (3)	O4—C12—C11	124.5 (3)
C1—C2—Br1A	120.3 (2)	C13—C12—C11	119.6 (3)
C3—C2—Br1A	117.8 (2)	C14—C13—C12	120.8 (3)
C4—C3—C2	119.1 (3)	C14—C13—H13	119.6
C4—C3—H3	120.5	C12—C13—H13	119.6
C2—C3—H3	120.5	C13—C14—C9	120.3 (3)
O1—C4—C3	124.1 (2)	C13—C14—H14	119.9
O1—C4—C5	115.7 (2)	C9—C14—H14	119.9
C3—C4—C5	120.3 (3)	O1—C15—H15A	109.5
O2—C5—C6	123.5 (2)	O1—C15—H15B	109.5
O2—C5—C4	116.9 (3)	H15A—C15—H15B	109.5
C6—C5—C4	119.6 (3)	O1—C15—H15C	109.5
C1—C6—C5	119.6 (3)	H15A—C15—H15C	109.5
C1—C6—C7	118.9 (3)	H15B—C15—H15C	109.5
C5—C6—C7	121.5 (3)	O4—C16—H16A	109.5
N1—C7—C6	119.7 (3)	O4—C16—H16B	109.5
N1—C7—H7	120.1	H16A—C16—H16B	109.5
C6—C7—H7	120.1	O4—C16—H16C	109.5
O3—C8—N2	121.5 (3)	H16A—C16—H16C	109.5
O3—C8—C9	121.2 (3)	H16B—C16—H16C	109.5
C7—N1—N2—C8	177.9 (3)	C1—C6—C7—N1	179.8 (3)
C6—C1—C2—C3	1.7 (5)	C5—C6—C7—N1	−0.7 (4)
C6—C1—C2—Br1A	−176.3 (2)	N1—N2—C8—O3	−2.6 (4)
C1—C2—C3—C4	−1.4 (4)	N1—N2—C8—C9	177.9 (2)
Br1A—C2—C3—C4	176.5 (2)	O3—C8—C9—C10	3.1 (4)
C15—O1—C4—C3	−10.0 (4)	N2—C8—C9—C10	−177.4 (2)
C15—O1—C4—C5	170.6 (3)	O3—C8—C9—C14	−177.1 (3)
C2—C3—C4—O1	−179.3 (3)	N2—C8—C9—C14	2.4 (4)
C2—C3—C4—C5	0.1 (4)	C14—C9—C10—C11	1.6 (4)
O1—C4—C5—O2	0.6 (4)	C8—C9—C10—C11	−178.5 (3)
C3—C4—C5—O2	−178.8 (3)	C9—C10—C11—C12	−0.2 (4)
O1—C4—C5—C6	−179.7 (3)	C16—O4—C12—C13	−178.2 (3)
C3—C4—C5—C6	0.9 (4)	C16—O4—C12—C11	1.8 (4)
C2—C1—C6—C5	−0.6 (4)	C10—C11—C12—O4	178.2 (3)
C2—C1—C6—C7	178.8 (3)	C10—C11—C12—C13	−1.9 (4)
O2—C5—C6—C1	179.0 (3)	O4—C12—C13—C14	−177.5 (3)
C4—C5—C6—C1	−0.6 (4)	C11—C12—C13—C14	2.5 (4)
O2—C5—C6—C7	−0.4 (4)	C12—C13—C14—C9	−1.1 (4)
C4—C5—C6—C7	179.9 (3)	C10—C9—C14—C13	−0.9 (4)
N2—N1—C7—C6	179.5 (2)	C8—C9—C14—C13	179.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O1Wi	0.86 (1)	1.96 (2)	2.820 (4)	174 (3)
O2—H2···N1	0.87 (3)	1.83 (3)	2.595 (3)	146 (5)
O1W—H1W···O2	0.85 (3)	2.23 (3)	2.974 (4)	147 (4)
O1W—H2W···O3ii	0.86 (3)	1.82 (3)	2.675 (3)	177 (4)
C16—H16C···Cg2iii	0.96	2.70	3.517 (3)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C9–C14 benzene ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21⋯O1W i	0.86 (1)	1.96 (2)	2.820 (4)	174 (3)
O2—H2⋯N1	0.87 (3)	1.83 (3)	2.595 (3)	146 (5)
O1W—H1W⋯O2	0.85 (3)	2.23 (3)	2.974 (4)	147 (4)
O1W—H2W⋯O3ii	0.86 (3)	1.82 (3)	2.675 (3)	177 (4)
C16—H16C⋯Cg2iii	0.96	2.70	3.517 (3)	144

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