N′-(5-Bromo-2-hydr­oxy-3-methoxy­benzyl­idene)-4-hydr­oxy-3-methoxy­benzohydrazide dihydrate

Lu, J.-F.; Min, S.-T.; Ge, H.-G.; Ji, X.-H.; Bai, Y.-F.

doi:10.1107/S1600536809033522

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2259

doi:10.1107/S1600536809033522

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N′-(5-Bromo-2-hydroxy-3-methoxybenzylidene)-4-hydroxy-3-methoxybenzohydrazide dihydrate

Jiu-Fu Lu,^a ^* Suo-Tian Min,^a Hong-Guang Ge,^a Xiao-Hui Ji ^a and Yue-Fei Bai ^b

^aSchool of Chemistry and Environmental Science, Shaanxi University of Technology, Hanzhong 723000, People's Republic of China, and ^bThe School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China
^*Correspondence e-mail: jiufulu@163.com

(Received 15 August 2009; accepted 22 August 2009; online 29 August 2009)

In the title compound, C₁₆H₁₅BrN₂O₅·2H₂O, the dihedral angle between the two aromatic rings is 2.9 (2)° and an intramolecular O—H⋯N hydrogen bond is observed. One of the water molecule is disordered over two positions, with occupancies of 0.83 (3) and 0.17 (3). In the crystal structure, molecules are linked into a three-dimensional network by intermolecular O—H⋯O, O—H⋯(O,O), O—H⋯N and N—H⋯O hydrogen bonds. π–π interactions involving Br-substituted benzene rings, with a centroid–centroid distance of 3.552 (3) Å are also observed.

Related literature

For related structures, see: Lu et al. (2008a ,b ,c ); Abdul Alhadi et al. (2009 ); Mohd Lair et al. (2009 ); Narayana et al. (2007 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₅BrN₂O₅·2H₂O
M_r = 431.24
Monoclinic, P 2₁ /c
a = 9.262 (2) Å
b = 8.679 (2) Å
c = 24.289 (5) Å
β = 112.42 (3)°
V = 1804.9 (8) Å³
Z = 4
Mo Kα radiation
μ = 2.32 mm⁻¹
T = 298 K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.618, T_max = 0.654
14447 measured reflections
3897 independent reflections
1997 reflections with I > 2σ(I)
R_int = 0.074

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.135
S = 1.02
3897 reflections
261 parameters
20 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7B⋯O1	0.85 (5)	2.34 (5)	2.875 (4)	122 (4)
O7—H7B⋯O2	0.85 (5)	2.22 (5)	3.027 (5)	159 (5)
O7—H7A⋯O6A	0.85 (5)	2.06 (2)	2.884 (10)	163 (6)
O6A—H6B⋯O7ⁱ	0.85 (1)	1.91 (4)	2.740 (8)	163 (5)
O6A—H6A⋯O3	0.85 (1)	1.92 (2)	2.715 (6)	154 (4)
N2—H2⋯O5ⁱⁱ	0.90	2.14	3.028 (4)	169
O5—H5⋯O6Bⁱⁱⁱ	0.82	1.85	2.64 (3)	163
O5—H5⋯O6Aⁱⁱⁱ	0.82	1.81	2.618 (5)	166
O1—H1⋯N1	0.82	1.83	2.550 (4)	145
Symmetry codes: (i) -x, -y+1, -z; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809033522/ci2888sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809033522/ci2888Isup2.hkl

checkCIF report

Comment top

Schiff bases and their metal complexes have received much attention in recent years. As part of our investigation on the crystal structures of Schiff bases derived from the condensation of aldehydes with benzohydrazides (Lu et al., 2008a,b,c), we report herein the crystal structure of the title new Schiff base compound.

The title compound (Fig. 1) consists of a Schiff base molecule and two water molecules of crystallization. The bond lengths have normal values (Allen et al., 1987) and are comparable to those observed in related structures (Abdul Alhadi et al., 2009; Mohd Lair et al., 2009; Narayana et al., 2007). The dihedral angle between the two aromatic rings is 2.9 (2)°, indicating that they are approximately coplanar. An intramolecular O—H···N hydrogen bond is observed (Fig. 1).

In the crystal structure, the molecules are linked into layers parallel to the ab direction by intermolecular N—H···O and O—H···O hydrogen bonds (Table 1 and Fig. 2).

Related literature top

For related structures, see: Lu et al. (2008a,b,c); Abdul Alhadi et al. (2009); Mohd Lair et al. (2009); Narayana et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by the Schiff base condensation of 5-bromo-2-hydroxy-3-methoxybenzaldehyde (0.1 mol) and 4-hydroxy-3-methoxybenzohydrazide (0.1 mmol) in 95% ethanol (50 ml). The excess ethanol was removed by distillation. The colourless solid obtained was filtered and washed with ethanol. Single crystals suitable for X-ray diffraction were obatined by slow evaporation of a 95% ethanol solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen bonds are shown as dashed lines. Only the major component of a disordered water molecule is shown.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

N'-(5-Bromo-2-hydroxy-3-methoxybenzylidene)-4-hydroxy-3-methoxybenzohydrazide dihydrate top

Crystal data top

C₁₆H₁₅BrN₂O₅·2H₂O	F(000) = 880
M_r = 431.24	D_x = 1.587 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1489 reflections
a = 9.262 (2) Å	θ = 2.4–24.5°
b = 8.679 (2) Å	µ = 2.32 mm⁻¹
c = 24.289 (5) Å	T = 298 K
β = 112.42 (3)°	Block, colourless
V = 1804.9 (8) Å³	0.23 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	3897 independent reflections
Radiation source: fine-focus sealed tube	1997 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
ω scans	θ_max = 27.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −11→11
T_min = 0.618, T_max = 0.654	k = −11→11
14447 measured reflections	l = −30→30

Refinement top

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + 0.9035P] where P = (F_o² + 2F_c²)/3
3897 reflections	(Δ/σ)_max = 0.001
261 parameters	Δρ_max = 0.32 e Å⁻³
20 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

C₁₆H₁₅BrN₂O₅·2H₂O	V = 1804.9 (8) Å³
M_r = 431.24	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.262 (2) Å	µ = 2.32 mm⁻¹
b = 8.679 (2) Å	T = 298 K
c = 24.289 (5) Å	0.23 × 0.20 × 0.20 mm
β = 112.42 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3897 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	1997 reflections with I > 2σ(I)
T_min = 0.618, T_max = 0.654	R_int = 0.074
14447 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	20 restraints
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.32 e Å⁻³
3897 reflections	Δρ_min = −0.53 e Å⁻³
261 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br1	0.61788 (6)	−0.03732 (7)	−0.13511 (3)	0.0778 (3)
O1	0.3146 (3)	0.3022 (4)	0.00769 (14)	0.0605 (9)
H1	0.3776	0.3517	0.0351	0.091*
O2	0.1468 (3)	0.1263 (4)	−0.07827 (14)	0.0692 (10)
O3	0.4712 (3)	0.5527 (4)	0.14385 (13)	0.0601 (8)
O4	1.1183 (3)	0.7762 (3)	0.28824 (13)	0.0570 (8)
O5	0.9838 (3)	0.9110 (3)	0.35146 (13)	0.0504 (8)
H5	0.9305	0.9520	0.3676	0.076*
N1	0.5836 (4)	0.4024 (4)	0.07415 (15)	0.0448 (9)
N2	0.6775 (4)	0.4898 (4)	0.12135 (14)	0.0446 (9)
H2	0.7808	0.4791	0.1320	0.054*
C1	0.5494 (5)	0.2381 (5)	−0.00796 (18)	0.0422 (10)
C2	0.3905 (5)	0.2269 (5)	−0.02205 (19)	0.0450 (10)
C3	0.3019 (5)	0.1318 (5)	−0.06863 (19)	0.0483 (11)
C4	0.3704 (5)	0.0548 (5)	−0.10141 (19)	0.0516 (11)
H4	0.3102	−0.0075	−0.1330	0.062*
C5	0.5288 (5)	0.0694 (5)	−0.08767 (19)	0.0515 (11)
C6	0.6186 (5)	0.1586 (5)	−0.04129 (18)	0.0477 (11)
H6	0.7255	0.1665	−0.0319	0.057*
C7	0.6451 (5)	0.3319 (5)	0.04189 (19)	0.0476 (11)
H7	0.7516	0.3412	0.0506	0.057*
C8	0.6112 (5)	0.5611 (5)	0.15561 (18)	0.0434 (10)
C9	0.7141 (4)	0.6511 (4)	0.20645 (17)	0.0392 (10)
C10	0.8737 (5)	0.6677 (4)	0.22134 (18)	0.0421 (10)
H10	0.9213	0.6195	0.1985	0.050*
C11	0.9612 (4)	0.7545 (4)	0.26950 (18)	0.0395 (10)
C12	0.8909 (5)	0.8267 (4)	0.30448 (17)	0.0389 (10)
C13	0.7334 (5)	0.8129 (5)	0.28971 (18)	0.0468 (11)
H13	0.6856	0.8622	0.3123	0.056*
C14	0.6469 (5)	0.7260 (5)	0.24137 (19)	0.0476 (11)
H14	0.5400	0.7168	0.2316	0.057*
C15	0.0554 (6)	0.0149 (6)	−0.1176 (2)	0.0779 (16)
H15A	0.0466	0.0389	−0.1573	0.117*
H15B	−0.0468	0.0134	−0.1161	0.117*
H15C	0.1033	−0.0844	−0.1063	0.117*
C16	1.1985 (5)	0.7209 (6)	0.2527 (2)	0.0680 (14)
H16A	1.1888	0.6109	0.2493	0.102*
H16B	1.3069	0.7484	0.2709	0.102*
H16C	1.1539	0.7662	0.2137	0.102*
O6A	0.1601 (5)	0.5145 (11)	0.0818 (2)	0.061 (3)	0.83 (3)
H6A	0.248 (2)	0.553 (4)	0.1037 (19)	0.091*
H6B	0.108 (4)	0.591 (4)	0.0621 (18)	0.091*
O6B	0.161 (3)	0.596 (5)	0.0998 (16)	0.071 (10)	0.17 (3)
O7	−0.0002 (3)	0.2697 (5)	0.00144 (17)	0.0817 (11)
H7A	0.055 (5)	0.327 (6)	0.0300 (19)	0.123*
H7B	0.059 (5)	0.221 (6)	−0.012 (2)	0.123*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0656 (4)	0.0946 (5)	0.0795 (4)	0.0048 (3)	0.0346 (3)	−0.0224 (3)
O1	0.0426 (18)	0.072 (2)	0.063 (2)	−0.0067 (16)	0.0166 (16)	−0.0216 (17)
O2	0.0376 (18)	0.089 (2)	0.078 (2)	−0.0146 (18)	0.0190 (17)	−0.030 (2)
O3	0.0332 (17)	0.078 (2)	0.064 (2)	−0.0127 (16)	0.0128 (15)	−0.0105 (17)
O4	0.0299 (16)	0.070 (2)	0.069 (2)	−0.0099 (15)	0.0168 (15)	−0.0251 (16)
O5	0.0427 (17)	0.058 (2)	0.0527 (19)	−0.0048 (15)	0.0208 (15)	−0.0106 (15)
N1	0.038 (2)	0.045 (2)	0.042 (2)	−0.0051 (17)	0.0047 (17)	0.0042 (17)
N2	0.0273 (17)	0.053 (2)	0.045 (2)	−0.0014 (16)	0.0042 (16)	−0.0033 (17)
C1	0.037 (2)	0.042 (3)	0.044 (3)	0.002 (2)	0.011 (2)	0.003 (2)
C2	0.045 (3)	0.042 (3)	0.049 (3)	0.002 (2)	0.019 (2)	0.000 (2)
C3	0.037 (2)	0.049 (3)	0.056 (3)	−0.002 (2)	0.015 (2)	−0.006 (2)
C4	0.051 (3)	0.048 (3)	0.050 (3)	−0.003 (2)	0.013 (2)	−0.008 (2)
C5	0.051 (3)	0.050 (3)	0.049 (3)	0.002 (2)	0.014 (2)	0.000 (2)
C6	0.037 (2)	0.058 (3)	0.047 (3)	0.001 (2)	0.015 (2)	0.005 (2)
C7	0.036 (2)	0.052 (3)	0.048 (3)	−0.001 (2)	0.009 (2)	0.007 (2)
C8	0.034 (2)	0.049 (3)	0.041 (2)	−0.003 (2)	0.007 (2)	0.010 (2)
C9	0.032 (2)	0.041 (2)	0.041 (2)	−0.0017 (18)	0.0101 (19)	0.0039 (19)
C10	0.041 (2)	0.039 (3)	0.046 (3)	0.0000 (19)	0.017 (2)	−0.003 (2)
C11	0.032 (2)	0.038 (2)	0.049 (3)	−0.0019 (19)	0.016 (2)	−0.001 (2)
C12	0.037 (2)	0.039 (2)	0.038 (2)	−0.0026 (19)	0.011 (2)	0.0047 (19)
C13	0.038 (2)	0.056 (3)	0.049 (3)	−0.004 (2)	0.019 (2)	−0.004 (2)
C14	0.032 (2)	0.055 (3)	0.057 (3)	−0.002 (2)	0.018 (2)	0.005 (2)
C15	0.049 (3)	0.082 (4)	0.092 (4)	−0.018 (3)	0.016 (3)	−0.016 (3)
C16	0.040 (3)	0.087 (4)	0.084 (4)	0.003 (3)	0.031 (3)	−0.023 (3)
O6A	0.037 (3)	0.081 (5)	0.056 (3)	−0.009 (2)	0.010 (2)	0.009 (3)
O6B	0.062 (12)	0.077 (14)	0.074 (13)	0.001 (8)	0.025 (9)	0.026 (8)
O7	0.048 (2)	0.112 (3)	0.083 (3)	0.000 (2)	0.0222 (18)	−0.002 (2)

Geometric parameters (Å, º) top

Br1—C5	1.895 (4)	C8—C9	1.465 (5)
O1—C2	1.353 (5)	C9—C10	1.389 (5)
O1—H1	0.82	C9—C14	1.390 (5)
O2—C3	1.365 (5)	C10—C11	1.367 (5)
O2—C15	1.396 (5)	C10—H10	0.93
O3—C8	1.218 (5)	C11—C12	1.400 (5)
O4—C11	1.361 (4)	C12—C13	1.368 (5)
O4—C16	1.421 (5)	C13—C14	1.368 (6)
O5—C12	1.353 (4)	C13—H13	0.93
O5—H5	0.82	C14—H14	0.93
N1—C7	1.286 (5)	C15—H15A	0.96
N1—N2	1.373 (4)	C15—H15B	0.96
N2—C8	1.357 (5)	C15—H15C	0.96
N2—H2	0.90	C16—H16A	0.96
C1—C2	1.382 (5)	C16—H16B	0.96
C1—C6	1.392 (5)	C16—H16C	0.96
C1—C7	1.448 (6)	O6A—O6B	0.83 (4)
C2—C3	1.388 (6)	O6A—H6A	0.851 (10)
C3—C4	1.367 (6)	O6A—H6B	0.853 (10)
C4—C5	1.381 (6)	O6B—H6A	0.856 (10)
C4—H4	0.93	O6B—H6B	0.858 (10)
C5—C6	1.358 (6)	O7—H7A	0.85 (5)
C6—H6	0.93	O7—H7B	0.85 (5)
C7—H7	0.93

C2—O1—H1	109.5	C11—C10—C9	120.3 (4)
C3—O2—C15	117.8 (4)	C11—C10—H10	119.8
C11—O4—C16	119.3 (3)	C9—C10—H10	119.8
C12—O5—H5	109.5	O4—C11—C10	124.8 (4)
C7—N1—N2	119.0 (3)	O4—C11—C12	114.8 (3)
C8—N2—N1	118.3 (3)	C10—C11—C12	120.3 (4)
C8—N2—H2	123.6	O5—C12—C13	122.7 (4)
N1—N2—H2	116.8	O5—C12—C11	117.4 (3)
C2—C1—C6	120.3 (4)	C13—C12—C11	119.9 (4)
C2—C1—C7	120.1 (4)	C14—C13—C12	119.3 (4)
C6—C1—C7	119.6 (4)	C14—C13—H13	120.3
O1—C2—C1	123.7 (4)	C12—C13—H13	120.3
O1—C2—C3	117.2 (4)	C13—C14—C9	122.0 (4)
C1—C2—C3	119.1 (4)	C13—C14—H14	119.0
O2—C3—C4	125.1 (4)	C9—C14—H14	119.0
O2—C3—C2	114.6 (4)	O2—C15—H15A	109.5
C4—C3—C2	120.3 (4)	O2—C15—H15B	109.5
C3—C4—C5	120.0 (4)	H15A—C15—H15B	109.5
C3—C4—H4	120.0	O2—C15—H15C	109.5
C5—C4—H4	120.0	H15A—C15—H15C	109.5
C6—C5—C4	120.7 (4)	H15B—C15—H15C	109.5
C6—C5—Br1	120.8 (3)	O4—C16—H16A	109.5
C4—C5—Br1	118.5 (3)	O4—C16—H16B	109.5
C5—C6—C1	119.5 (4)	H16A—C16—H16B	109.5
C5—C6—H6	120.2	O4—C16—H16C	109.5
C1—C6—H6	120.2	H16A—C16—H16C	109.5
N1—C7—C1	120.3 (4)	H16B—C16—H16C	109.5
N1—C7—H7	119.8	O6B—O6A—H6A	61.2 (18)
C1—C7—H7	119.8	O6B—O6A—H6B	61.3 (17)
O3—C8—N2	121.2 (4)	H6A—O6A—H6B	104 (2)
O3—C8—C9	121.5 (4)	O6A—O6B—H6A	60.6 (18)
N2—C8—C9	117.3 (4)	O6A—O6B—H6B	60.6 (18)
C10—C9—C14	118.2 (4)	H6A—O6B—H6B	103 (2)
C10—C9—C8	124.1 (4)	H7A—O7—H7B	109 (3)
C14—C9—C8	117.7 (4)

C7—N1—N2—C8	−178.8 (4)	N1—N2—C8—O3	−2.5 (6)
C6—C1—C2—O1	−179.1 (4)	N1—N2—C8—C9	178.8 (3)
C7—C1—C2—O1	1.3 (6)	O3—C8—C9—C10	−178.6 (4)
C6—C1—C2—C3	2.0 (6)	N2—C8—C9—C10	0.2 (6)
C7—C1—C2—C3	−177.6 (4)	O3—C8—C9—C14	0.5 (6)
C15—O2—C3—C4	11.5 (7)	N2—C8—C9—C14	179.2 (3)
C15—O2—C3—C2	−169.8 (4)	C14—C9—C10—C11	0.6 (6)
O1—C2—C3—O2	−0.2 (6)	C8—C9—C10—C11	179.7 (4)
C1—C2—C3—O2	178.8 (4)	C16—O4—C11—C10	7.5 (6)
O1—C2—C3—C4	178.6 (4)	C16—O4—C11—C12	−173.8 (4)
C1—C2—C3—C4	−2.4 (6)	C9—C10—C11—O4	179.1 (4)
O2—C3—C4—C5	179.8 (4)	C9—C10—C11—C12	0.4 (6)
C2—C3—C4—C5	1.1 (7)	O4—C11—C12—O5	1.3 (5)
C3—C4—C5—C6	0.7 (7)	C10—C11—C12—O5	−179.9 (3)
C3—C4—C5—Br1	−179.1 (3)	O4—C11—C12—C13	179.8 (3)
C4—C5—C6—C1	−1.1 (6)	C10—C11—C12—C13	−1.4 (6)
Br1—C5—C6—C1	178.7 (3)	O5—C12—C13—C14	179.7 (4)
C2—C1—C6—C5	−0.2 (6)	C11—C12—C13—C14	1.2 (6)
C7—C1—C6—C5	179.3 (4)	C12—C13—C14—C9	−0.2 (6)
N2—N1—C7—C1	179.6 (3)	C10—C9—C14—C13	−0.8 (6)
C2—C1—C7—N1	1.6 (6)	C8—C9—C14—C13	−179.9 (4)
C6—C1—C7—N1	−178.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7B···O1	0.85 (5)	2.34 (5)	2.875 (4)	122 (4)
O7—H7B···O2	0.85 (5)	2.22 (5)	3.027 (5)	159 (5)
O7—H7A···O6A	0.85 (5)	2.06 (2)	2.884 (10)	163 (6)
O6A—H6B···O7ⁱ	0.85 (1)	1.91 (4)	2.740 (8)	163 (5)
O6A—H6A···O3	0.85 (1)	1.92 (2)	2.715 (6)	154 (4)
N2—H2···O5ⁱⁱ	0.90	2.14	3.028 (4)	169
O5—H5···O6Bⁱⁱⁱ	0.82	1.85	2.64 (3)	163
O5—H5···O6Aⁱⁱⁱ	0.82	1.81	2.618 (5)	166
O1—H1···N1	0.82	1.83	2.550 (4)	145

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+2, y−1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅BrN₂O₅·2H₂O
M_r	431.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.262 (2), 8.679 (2), 24.289 (5)
β (°)	112.42 (3)
V (Å³)	1804.9 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.32
Crystal size (mm)	0.23 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.618, 0.654
No. of measured, independent and observed [I > 2σ(I)] reflections	14447, 3897, 1997
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.135, 1.02
No. of reflections	3897
No. of parameters	261
No. of restraints	20
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.53

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7B···O1	0.85 (5)	2.34 (5)	2.875 (4)	122 (4)
O7—H7B···O2	0.85 (5)	2.22 (5)	3.027 (5)	159 (5)
O7—H7A···O6A	0.85 (5)	2.06 (2)	2.884 (10)	163 (6)
O6A—H6B···O7ⁱ	0.85 (1)	1.91 (4)	2.740 (8)	163 (5)
O6A—H6A···O3	0.85 (1)	1.92 (2)	2.715 (6)	154 (4)
N2—H2···O5ⁱⁱ	0.90	2.14	3.028 (4)	169
O5—H5···O6Bⁱⁱⁱ	0.82	1.85	2.64 (3)	163
O5—H5···O6Aⁱⁱⁱ	0.82	1.81	2.618 (5)	166
O1—H1···N1	0.82	1.83	2.550 (4)	145

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+2, y−1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2.

Acknowledgements

The authors thank the Scientific Research Foundation of Shaanxi University of Technology for financial support (project No. SLGQD0708).

References

Abdul Alhadi, A. A., Ali, H. M. & Ng, S. W. (2009). Acta Cryst. E65, o908. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008a). Acta Cryst. E64, o1693. Web of Science CSD CrossRef IUCr Journals Google Scholar
Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008b). Acta Cryst. E64, o1694. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Narayana, B., Siddaraju, B. P., Raju, C. R., Yathirajan, H. S. & Bolte, M. (2007). Acta Cryst. E63, o3522. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N′-(5-Bromo-2-hydr­­oxy-3-meth­oxy­benzyl­­idene)-4-hydr­­oxy-3-meth­oxy­benzohydrazide dihydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-(5-Bromo-2-hydroxy-3-methoxybenzylidene)-4-hydroxy-3-methoxybenzohydrazide dihydrate