N′-[1-(5-Bromo-2-hydroxy­phen­yl)ethyl­idene]-3,4,5-trihydroxy­benzohydrazide dimethyl sulfoxide solvate trihydrate

Suleiman Gwaram, N.; Khaledi, H.; Mohd Ali, H.; Robinson, W.T.; Abdulla, M.A.

doi:10.1107/S1600536810007002

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o721

doi:10.1107/S1600536810007002

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N′-[1-(5-Bromo-2-hydroxyphenyl)ethylidene]-3,4,5-trihydroxybenzohydrazide dimethyl sulfoxide solvate trihydrate

Nura Suleiman Gwaram,^a Hamid Khaledi,^a ^* Hapipah Mohd Ali,^a Ward T. Robinson ^a and Mahmood A. Abdulla ^b

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^bDepartment of Molecular Medicine, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: khaledi@perdana.um.edu.my

(Received 10 February 2010; accepted 24 February 2010; online 27 February 2010)

The benzohydrazide molecule in the title compound, C₁₅H₁₃BrN₂O₅·C₂H₆OS·3H₂O, is almost planar with an r.m.s. deviation for the non-H atoms of 0.078 Å. The organic molecules, water and dimethyl sulfoxide solvent molecules are linked by N—H⋯O, O—H⋯O and O—H⋯S intermolecular hydrogen bonds, forming zigzag chains along the a axis. Intramolecular 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_r = 513.36
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.029
wR(F²) = 0.066
S = 1.02
3694 reflections
307 parameters
11 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.30 e Å⁻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⋯O2^iv	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⋯O2^v	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⋯O9^vi	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) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) -x+1, -y+2, -z+2; (iii) $[-x, y, -z+{\script{3\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (v) x-1, y, z; (vi) -x, -y+2, -z+2.

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 ).

Supporting information

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

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

checkCIF report

Related literature top

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 drived from 3,4,5-trihydroxybenzoylhydrazide, see: Abdul Alhadi et al. (2009); Khaledi et al. (2009).

Experimental top

A mixture of 5-bromo-2-hydroxyacetophenone (2.15 g, 10 mmol) and 3,4,5-trihydroxybenzoylhydrazine(1.84 g, 10 mmol) was heated in ethanol (70 ml) for 3 h. The solution was then cooled and the solid product formed weas filtered off, washed with cold ethanol,and dried over silica gel. Crystals of the title compound were obtained by slow evaporation of a DMSO solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the title compound at 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Zigzag chain along α axis formed by intermolecular hydrogen bonding

N'-[1-(5-Bromo-2-hydroxyphenyl)ethylidene]-3,4,5- trihydroxybenzohydrazide dimethyl sulfoxide solvate trihydrate top

Crystal data top

C₁₅H₁₃BrN₂O₅·C₂H₆OS·3H₂O	F(000) = 2112
M_r = 513.36	D_x = 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

Data collection top

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

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)] = 0.029	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(F_o²) + (0.0311P)² + 3.5353P] where P = (F_o² + 2F_c²)/3
3694 reflections	(Δ/σ)_max = 0.001
307 parameters	Δρ_max = 0.34 e Å⁻³
11 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₅H₁₃BrN₂O₅·C₂H₆OS·3H₂O	V = 4206.4 (5) Å³
M_r = 513.36	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 21.5690 (15) Å	µ = 2.11 mm⁻¹
b = 7.0302 (4) Å	T = 100 K
c = 28.4771 (18) Å	0.26 × 0.03 × 0.03 mm
β = 103.061 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3694 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3052 reflections with I > 2σ(I)
T_min = 0.610, T_max = 0.940	R_int = 0.030
9543 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	11 restraints
wR(F²) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.34 e Å⁻³
3694 reflections	Δρ_min = −0.30 e Å⁻³
307 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 > 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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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···O2^iv	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···O2^v	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···O9^vi	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) x+1/2, y+1/2, z; (ii) −x+1, −y+2, −z+2; (iii) −x, y, −z+3/2; (iv) x−1/2, y+1/2, z; (v) x−1, y, z; (vi) −x, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃BrN₂O₅·C₂H₆OS·3H₂O
M_r	513.36
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	21.5690 (15), 7.0302 (4), 28.4771 (18)
β (°)	103.061 (2)
V (Å³)	4206.4 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.11
Crystal size (mm)	0.26 × 0.03 × 0.03

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.610, 0.940
No. of measured, independent and observed [I > 2σ(I)] reflections	9543, 3694, 3052
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.066, 1.02
No. of reflections	3694
No. of parameters	307
No. of restraints	11
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.30

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.818 (17)	1.80 (2)	2.531 (3)	149 (3)
O1—H1···O9	0.818 (17)	2.65 (2)	3.338 (2)	142 (3)
O2—H2A···O10ⁱ	0.839 (17)	1.877 (18)	2.703 (2)	168 (3)
O2—H2A···Sⁱ	0.839 (17)	2.86 (2)	3.5458 (19)	140 (2)
O2—H2B···O1ⁱⁱ	0.830 (17)	2.060 (18)	2.880 (2)	169 (3)
O3—H3A···O10	0.823 (17)	1.973 (18)	2.785 (3)	169 (3)
O3—H3B···O13ⁱⁱⁱ	0.804 (17)	2.012 (18)	2.802 (2)	168 (3)
O4—H4A···O2^iv	0.867 (18)	2.07 (2)	2.915 (3)	166 (3)
O4—H4B···O3	0.889 (18)	1.96 (2)	2.817 (3)	160 (3)
O12—H12···O3	0.837 (18)	1.913 (18)	2.751 (2)	179 (3)
O13—H13···O2^v	0.803 (17)	1.883 (19)	2.651 (2)	160 (3)
O13—H13···O14	0.803 (17)	2.30 (3)	2.727 (2)	114 (2)
O14—H14···O9^vi	0.821 (17)	1.871 (18)	2.682 (2)	169 (3)
N2—H2N···O4	0.870 (10)	2.243 (10)	3.113 (3)	179 (3)

Symmetry codes: (i) x+1/2, y+1/2, z; (ii) −x+1, −y+2, −z+2; (iii) −x, y, −z+3/2; (iv) x−1/2, y+1/2, z; (v) x−1, y, z; (vi) −x, −y+2, −z+2.

Acknowledgements

The authors thank the University of Malaya for funding this study (UMRG grant No. RG136/09HTM).

References

Abdul Alhadi, A. A., Ali, H. M. & Ng, S. W. (2009). Acta Cryst. E65, o910. Web of Science CSD CrossRef IUCr Journals Google Scholar
Arunkumar, S., Ramalakshmi, N., Saraswathy, T. & Aruloly, L. (2006). Indian J. Heterocycl. Chem. 16, 29–32. CAS Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Khaledi, H., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, o169. Web of Science CSD CrossRef IUCr Journals Google Scholar
Saxena, H. O., Faridi, U., Srivastava, S., Kumar, J. K., Darokar, M. P., Luqman, S., Chanotiya, C. S., Krishna, V., Negi, A. S. & Khanuja, S. P. S. (2008). Bioorg. Med. Chem. Lett. 18, 3914–3918. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). publCIF. In preparation. Google Scholar

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Volume 66| Part 3| March 2010| Page o721

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

N′-[1-(5-Bromo-2-hy­droxy­phen­yl)ethyl­­idene]-3,4,5-tri­hydroxy­benzohydrazide di­methyl sulfoxide solvate trihydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-[1-(5-Bromo-2-hydroxyphenyl)ethylidene]-3,4,5-trihydroxybenzohydrazide dimethyl sulfoxide solvate trihydrate