N'-[1-(5-Bromo-2-hydroxy-phen-yl)ethyl-idene]-3,4,5-trihydroxy-benzohydrazide dimethyl sulfoxide solvate trihydrate.

The benzohydrazide mol-ecule in the title compound, C(15)H(13)BrN(2)O(5)·C(2)H(6)OS·3H(2)O, is almost planar with an r.m.s. deviation for the non-H atoms of 0.078 Å. The organic mol-ecules, water and dimethyl sulfoxide solvent mol-ecules are linked by N-H⋯O, O-H⋯O and O-H⋯S inter-molecular hydrogen bonds, forming zigzag chains along the a axis. Intra-molecular O-H⋯O and O-H⋯N hydrogen bonds also occur.

Related literature

For the biological properties of 3,4,5-trihydroxy­benzoic acid (gallic acid) derivatives, see: Arunkumar et al. (2006 ▶); Saxena et al. (2008 ▶). For the crystal structures of Schiff bases derived from 3,4,5-trihydroxy­benzoyl­hydrazide, see: Abdul Alhadi et al. (2009 ▶); Khaledi et al. (2009 ▶).

Experimental

Crystal data

C15H13BrN2O5·C2H6OS·3H2O

M = 513.36

Monoclinic,

a = 21.5690 (15) Å

b = 7.0302 (4) Å

c = 28.4771 (18) Å

β = 103.061 (2)°

V = 4206.4 (5) Å3

Z = 8

Mo Kα radiation

μ = 2.11 mm−1

T = 100 K

0.26 × 0.03 × 0.03 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.610, T max = 0.940

9543 measured reflections

3694 independent reflections

3052 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.066

S = 1.02

3694 reflections

307 parameters

11 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.30 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810007002/hg2645sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007002/hg2645Isup2.hkl

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

C15H13BrN2O5·C2H6OS·3H2O	F(000) = 2112
Mr = 513.36	Dx = 1.621 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3053 reflections
a = 21.5690 (15) Å	θ = 2.7–27.9°
b = 7.0302 (4) Å	µ = 2.11 mm−1
c = 28.4771 (18) Å	T = 100 K
β = 103.061 (2)°	Needle, colourless
V = 4206.4 (5) Å3	0.26 × 0.03 × 0.03 mm
Z = 8

Bruker APEXII CCD area-detector diffractometer	3694 independent reflections
Radiation source: fine-focus sealed tube	3052 reflections with I > 2σ(I)
graphite	Rint = 0.030
phi and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→25
Tmin = 0.610, Tmax = 0.940	k = −8→5
9543 measured reflections	l = −33→33

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0311P)2 + 3.5353P] where P = (Fo2 + 2Fc2)/3
3694 reflections	(Δ/σ)max = 0.001
307 parameters	Δρmax = 0.34 e Å−3
11 restraints	Δρmin = −0.30 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 > 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
Br	0.525034 (11)	1.15033 (4)	1.066977 (9)	0.01977 (9)
S	0.15785 (3)	0.18073 (10)	0.73419 (2)	0.02470 (17)
O1	0.25101 (8)	1.0736 (3)	1.07882 (6)	0.0201 (4)
H1	0.2293 (12)	1.052 (4)	1.0519 (7)	0.030*
O2	0.78049 (8)	0.7413 (3)	0.83940 (6)	0.0205 (4)
H2A	0.7527 (12)	0.791 (4)	0.8174 (8)	0.031*
H2B	0.7763 (14)	0.801 (4)	0.8636 (8)	0.031*
O3	0.12345 (8)	0.6895 (3)	0.77600 (6)	0.0193 (4)
H3A	0.1436 (13)	0.590 (3)	0.7769 (11)	0.029*
H3B	0.1157 (13)	0.721 (4)	0.7481 (7)	0.029*
O4	0.19398 (10)	0.9307 (3)	0.84748 (7)	0.0382 (5)
H4A	0.2210 (14)	1.012 (4)	0.8408 (12)	0.057*
H4B	0.1779 (16)	0.866 (4)	0.8207 (9)	0.057*
O9	0.11275 (8)	0.9528 (3)	1.00576 (6)	0.0188 (4)
O10	0.18508 (9)	0.3495 (3)	0.76525 (6)	0.0288 (5)
O12	0.00733 (8)	0.7056 (3)	0.80056 (6)	0.0302 (5)
H12	0.0426 (10)	0.702 (5)	0.7930 (11)	0.045*
O13	−0.10287 (8)	0.7412 (3)	0.82391 (6)	0.0210 (4)
H13	−0.1337 (11)	0.749 (4)	0.8352 (10)	0.032*
O14	−0.11122 (8)	0.8463 (3)	0.91444 (6)	0.0213 (4)
H14	−0.1073 (14)	0.900 (4)	0.9405 (7)	0.032*
N1	0.22497 (9)	0.9902 (3)	0.99005 (7)	0.0148 (5)
N2	0.17589 (9)	0.9350 (3)	0.95289 (7)	0.0146 (5)
H2N	0.1813 (11)	0.933 (4)	0.9235 (5)	0.018*
C1	0.31207 (11)	1.0888 (4)	1.07379 (8)	0.0156 (5)
C2	0.35764 (12)	1.1406 (4)	1.11456 (9)	0.0186 (6)
H2	0.3452	1.1618	1.1441	0.022*
C3	0.42073 (11)	1.1617 (4)	1.11280 (9)	0.0175 (6)
H3	0.4516	1.1992	1.1407	0.021*
C4	0.43828 (11)	1.1272 (3)	1.06974 (9)	0.0156 (5)
C5	0.39418 (11)	1.0743 (3)	1.02900 (9)	0.0150 (5)
H5	0.4074	1.0523	0.9998	0.018*
C6	0.32987 (11)	1.0524 (3)	1.02996 (8)	0.0135 (5)
C7	0.28342 (11)	0.9907 (3)	0.98599 (8)	0.0143 (5)
C8	0.30638 (12)	0.9305 (4)	0.94239 (9)	0.0199 (6)
H8A	0.2713	0.8716	0.9190	0.030*
H8B	0.3411	0.8386	0.9519	0.030*
H8C	0.3218	1.0420	0.9278	0.030*
C9	0.11782 (11)	0.9227 (3)	0.96425 (9)	0.0148 (5)
C10	0.06185 (11)	0.8702 (3)	0.92563 (8)	0.0131 (5)
C11	0.06462 (11)	0.8147 (4)	0.87924 (8)	0.0157 (6)
H11	0.1045	0.8087	0.8703	0.019*
C12	0.00928 (12)	0.7683 (4)	0.84614 (8)	0.0172 (6)
C13	−0.04955 (11)	0.7827 (4)	0.85844 (8)	0.0146 (5)
C14	−0.05204 (11)	0.8373 (4)	0.90472 (8)	0.0142 (5)
C15	0.00347 (11)	0.8764 (3)	0.93839 (9)	0.0145 (5)
H15	0.0017	0.9078	0.9705	0.017*
C16	0.07421 (15)	0.1949 (6)	0.72909 (17)	0.0685 (13)
H16A	0.0645	0.1626	0.7601	0.103*
H16B	0.0525	0.1053	0.7044	0.103*
H16C	0.0596	0.3244	0.7199	0.103*
C17	0.15995 (19)	0.2421 (5)	0.67432 (11)	0.0490 (10)
H17A	0.1387	0.3648	0.6661	0.074*
H17B	0.1380	0.1441	0.6522	0.074*
H17C	0.2043	0.2514	0.6715	0.074*

	U11	U22	U33	U12	U13	U23
Br	0.01221 (13)	0.01949 (15)	0.02680 (15)	−0.00176 (11)	0.00269 (10)	−0.00108 (12)
S	0.0249 (4)	0.0245 (4)	0.0222 (4)	0.0041 (3)	0.0002 (3)	−0.0006 (3)
O1	0.0126 (9)	0.0320 (11)	0.0155 (9)	−0.0023 (8)	0.0028 (7)	−0.0048 (9)
O2	0.0159 (10)	0.0290 (12)	0.0152 (9)	0.0006 (8)	0.0008 (8)	−0.0027 (8)
O3	0.0213 (10)	0.0236 (11)	0.0122 (9)	0.0033 (8)	0.0024 (8)	0.0000 (8)
O4	0.0409 (13)	0.0487 (15)	0.0254 (11)	−0.0210 (11)	0.0085 (10)	−0.0066 (11)
O9	0.0167 (9)	0.0261 (11)	0.0130 (9)	−0.0026 (8)	0.0022 (7)	−0.0036 (8)
O10	0.0270 (10)	0.0291 (11)	0.0246 (10)	0.0053 (9)	−0.0059 (8)	−0.0063 (9)
O12	0.0153 (9)	0.0640 (15)	0.0116 (9)	−0.0023 (10)	0.0038 (8)	−0.0127 (9)
O13	0.0102 (9)	0.0382 (12)	0.0145 (9)	−0.0028 (9)	0.0025 (7)	−0.0065 (9)
O14	0.0132 (8)	0.0364 (12)	0.0155 (9)	−0.0028 (8)	0.0058 (7)	−0.0116 (9)
N1	0.0130 (11)	0.0138 (11)	0.0153 (11)	−0.0025 (9)	−0.0017 (8)	−0.0010 (9)
N2	0.0137 (10)	0.0193 (12)	0.0102 (10)	−0.0011 (9)	0.0011 (8)	−0.0016 (10)
C1	0.0152 (13)	0.0142 (13)	0.0168 (13)	−0.0005 (10)	0.0021 (10)	0.0012 (11)
C2	0.0199 (13)	0.0199 (14)	0.0160 (13)	−0.0009 (12)	0.0040 (10)	−0.0032 (12)
C3	0.0174 (13)	0.0161 (14)	0.0155 (12)	−0.0001 (11)	−0.0036 (10)	−0.0021 (11)
C4	0.0116 (12)	0.0113 (13)	0.0236 (14)	−0.0015 (10)	0.0033 (10)	0.0012 (11)
C5	0.0182 (13)	0.0113 (13)	0.0161 (13)	−0.0006 (11)	0.0053 (10)	0.0016 (11)
C6	0.0161 (12)	0.0098 (13)	0.0138 (12)	0.0018 (11)	0.0020 (10)	0.0010 (10)
C7	0.0168 (13)	0.0124 (13)	0.0126 (12)	0.0007 (10)	0.0009 (10)	0.0013 (10)
C8	0.0169 (13)	0.0268 (15)	0.0157 (13)	−0.0021 (12)	0.0028 (11)	−0.0017 (12)
C9	0.0162 (13)	0.0096 (13)	0.0182 (13)	0.0012 (11)	0.0031 (10)	0.0018 (11)
C10	0.0148 (12)	0.0088 (13)	0.0152 (12)	0.0000 (10)	0.0021 (10)	0.0013 (11)
C11	0.0129 (12)	0.0210 (15)	0.0143 (12)	0.0021 (11)	0.0053 (10)	0.0001 (11)
C12	0.0195 (13)	0.0204 (14)	0.0116 (12)	0.0007 (11)	0.0034 (10)	−0.0012 (11)
C13	0.0123 (12)	0.0174 (14)	0.0127 (12)	−0.0004 (10)	−0.0003 (10)	0.0004 (11)
C14	0.0137 (12)	0.0131 (13)	0.0166 (12)	−0.0017 (11)	0.0051 (10)	−0.0011 (11)
C15	0.0163 (12)	0.0149 (14)	0.0127 (12)	−0.0004 (11)	0.0039 (10)	−0.0033 (11)
C16	0.0242 (18)	0.065 (3)	0.112 (4)	−0.0043 (18)	0.007 (2)	−0.042 (3)
C17	0.084 (3)	0.034 (2)	0.0243 (16)	−0.009 (2)	0.0029 (17)	−0.0009 (15)

Br—C4	1.898 (2)	C2—H2	0.9500
S—O10	1.516 (2)	C3—C4	1.384 (3)
S—C17	1.769 (3)	C3—H3	0.9500
S—C16	1.780 (3)	C4—C5	1.375 (3)
O1—C1	1.361 (3)	C5—C6	1.402 (3)
O1—H1	0.818 (17)	C5—H5	0.9500
O2—H2A	0.839 (17)	C6—C7	1.481 (3)
O2—H2B	0.830 (17)	C7—C8	1.498 (3)
O3—H3A	0.823 (17)	C8—H8A	0.9800
O3—H3B	0.804 (17)	C8—H8B	0.9800
O4—H4A	0.867 (18)	C8—H8C	0.9800
O4—H4B	0.889 (18)	C9—C10	1.484 (3)
O9—C9	1.230 (3)	C10—C15	1.388 (3)
O12—C12	1.363 (3)	C10—C11	1.391 (3)
O12—H12	0.837 (18)	C11—C12	1.383 (3)
O13—C13	1.365 (3)	C11—H11	0.9500
O13—H13	0.803 (17)	C12—C13	1.394 (3)
O14—C14	1.368 (3)	C13—C14	1.385 (3)
O14—H14	0.821 (17)	C14—C15	1.382 (3)
N1—C7	1.292 (3)	C15—H15	0.9500
N1—N2	1.373 (3)	C16—H16A	0.9800
N2—C9	1.365 (3)	C16—H16B	0.9800
N2—H2N	0.870 (10)	C16—H16C	0.9800
C1—C2	1.389 (3)	C17—H17A	0.9800
C1—C6	1.410 (3)	C17—H17B	0.9800
C2—C3	1.381 (3)	C17—H17C	0.9800
O10—S—C17	106.27 (14)	H8A—C8—H8B	109.5
O10—S—C16	104.83 (14)	C7—C8—H8C	109.5
C17—S—C16	98.9 (2)	H8A—C8—H8C	109.5
C1—O1—H1	106 (2)	H8B—C8—H8C	109.5
H2A—O2—H2B	103 (3)	O9—C9—N2	120.2 (2)
H3A—O3—H3B	105 (3)	O9—C9—C10	121.4 (2)
H4A—O4—H4B	107 (3)	N2—C9—C10	118.4 (2)
C12—O12—H12	115 (2)	C15—C10—C11	119.6 (2)
C13—O13—H13	110 (2)	C15—C10—C9	115.6 (2)
C14—O14—H14	107 (2)	C11—C10—C9	124.8 (2)
C7—N1—N2	122.0 (2)	C12—C11—C10	119.8 (2)
C9—N2—N1	115.11 (19)	C12—C11—H11	120.1
C9—N2—H2N	123.8 (17)	C10—C11—H11	120.1
N1—N2—H2N	119.9 (17)	O12—C12—C11	124.2 (2)
O1—C1—C2	116.8 (2)	O12—C12—C13	115.4 (2)
O1—C1—C6	122.9 (2)	C11—C12—C13	120.4 (2)
C2—C1—C6	120.3 (2)	O13—C13—C14	122.5 (2)
C3—C2—C1	121.0 (2)	O13—C13—C12	118.0 (2)
C3—C2—H2	119.5	C14—C13—C12	119.5 (2)
C1—C2—H2	119.5	O14—C14—C15	123.5 (2)
C2—C3—C4	118.8 (2)	O14—C14—C13	116.4 (2)
C2—C3—H3	120.6	C15—C14—C13	120.1 (2)
C4—C3—H3	120.6	C14—C15—C10	120.5 (2)
C5—C4—C3	121.3 (2)	C14—C15—H15	119.8
C5—C4—Br	119.25 (18)	C10—C15—H15	119.8
C3—C4—Br	119.44 (18)	S—C16—H16A	109.5
C4—C5—C6	120.8 (2)	S—C16—H16B	109.5
C4—C5—H5	119.6	H16A—C16—H16B	109.5
C6—C5—H5	119.6	S—C16—H16C	109.5
C5—C6—C1	117.8 (2)	H16A—C16—H16C	109.5
C5—C6—C7	119.9 (2)	H16B—C16—H16C	109.5
C1—C6—C7	122.3 (2)	S—C17—H17A	109.5
N1—C7—C6	114.4 (2)	S—C17—H17B	109.5
N1—C7—C8	125.8 (2)	H17A—C17—H17B	109.5
C6—C7—C8	119.8 (2)	S—C17—H17C	109.5
C7—C8—H8A	109.5	H17A—C17—H17C	109.5
C7—C8—H8B	109.5	H17B—C17—H17C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82 (2)	1.80 (2)	2.531 (3)	149 (3)
O1—H1···O9	0.82 (2)	2.65 (2)	3.338 (2)	142 (3)
O2—H2A···O10i	0.84 (2)	1.88 (2)	2.703 (2)	168 (3)
O2—H2A···Si	0.84 (2)	2.86 (2)	3.5458 (19)	140 (2)
O2—H2B···O1ii	0.83 (2)	2.06 (2)	2.880 (2)	169 (3)
O3—H3A···O10	0.82 (2)	1.97 (2)	2.785 (3)	169 (3)
O3—H3B···O13iii	0.80 (2)	2.01 (2)	2.802 (2)	168 (3)
O4—H4A···O2iv	0.87 (2)	2.07 (2)	2.915 (3)	166 (3)
O4—H4B···O3	0.89 (2)	1.96 (2)	2.817 (3)	160 (3)
O12—H12···O3	0.84 (2)	1.91 (2)	2.751 (2)	179 (3)
O13—H13···O2v	0.80 (2)	1.88 (2)	2.651 (2)	160 (3)
O13—H13···O14	0.80 (2)	2.30 (3)	2.727 (2)	114 (2)
O14—H14···O9vi	0.82 (2)	1.87 (2)	2.682 (2)	169 (3)
N2—H2N···O4	0.87 (1)	2.24 (1)	3.113 (3)	179 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82 (2)	1.80 (2)	2.531 (3)	149 (3)
O1—H1⋯O9	0.82 (2)	2.65 (2)	3.338 (2)	142 (3)
O2—H2A⋯O10i	0.84 (2)	1.88 (2)	2.703 (2)	168 (3)
O2—H2A⋯Si	0.84 (2)	2.86 (2)	3.5458 (19)	140 (2)
O2—H2B⋯O1ii	0.83 (2)	2.06 (2)	2.880 (2)	169 (3)
O3—H3A⋯O10	0.82 (2)	1.97 (2)	2.785 (3)	169 (3)
O3—H3B⋯O13iii	0.80 (2)	2.01 (2)	2.802 (2)	168 (3)
O4—H4A⋯O2iv	0.87 (2)	2.07 (2)	2.915 (3)	166 (3)
O4—H4B⋯O3	0.89 (2)	1.96 (2)	2.817 (3)	160 (3)
O12—H12⋯O3	0.84 (2)	1.91 (2)	2.751 (2)	179 (3)
O13—H13⋯O2v	0.80 (2)	1.88 (2)	2.651 (2)	160 (3)
O13—H13⋯O14	0.80 (2)	2.30 (3)	2.727 (2)	114 (2)
O14—H14⋯O9vi	0.82 (2)	1.87 (2)	2.682 (2)	169 (3)
N2—H2N⋯O4	0.87 (1)	2.24 (1)	3.113 (3)	179 (3)

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