N′-(5-Bromo-2-hydroxy­benzyl­idene)-3,4,5-trihydroxy­benzohydrazide dihydrate

Alhadi, A.A.; Ali, H.M.; Puvaneswary, S.; Robinson, W.T.; Ng, S.W.

doi:10.1107/S1600536808022708

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1584

doi:10.1107/S1600536808022708

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N′-(5-Bromo-2-hydroxybenzylidene)-3,4,5-trihydroxybenzohydrazide dihydrate

Abeer A. Alhadi,^a Hapipah M. Ali,^a Subramaniam Puvaneswary,^a Ward T. Robinson ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 16 July 2008; accepted 19 July 2008; online 23 July 2008)

The title compound, C₁₄H₁₁BrN₂O₅·2H₂O, crystallizes as hydrogen-bonded sheets. The 2-hydroxy group on the benzylidene group forms an intramolecular hydrogen bond to the N atom of the C=N double bond. The amino N atom is a hydrogen-bond donor to a water molecule. The hydroxy group on the benzohydrazide group is a hydrogen-bond donor to one acceptor site, whereas each water molecule is a hydrogen-bond donor to two acceptor sites.

Related literature

For the structure of a similar Schiff-base ligand, 5-bromosalicylaldehyde benzoylhydrazone, see: Liu et al. (2006 ).

Experimental

Crystal data

C₁₄H₁₁BrN₂O₅·2H₂O
M_r = 403.19
Monoclinic, P 2₁ /c
a = 30.8424 (8) Å
b = 3.7999 (1) Å
c = 12.8484 (4) Å
β = 90.280 (2)°
V = 1505.79 (7) Å³
Z = 4
Mo Kα radiation
μ = 2.77 mm⁻¹
T = 100 (2) K
0.30 × 0.03 × 0.03 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.658, T_max = 0.921
9964 measured reflections
3424 independent reflections
2914 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.155
S = 1.22
3424 reflections
241 parameters
10 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.08 e Å⁻³
Δρ_min = −1.82 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.84 (1)	1.91 (5)	2.616 (6)	141 (7)
O3—H3o⋯O2w	0.84 (1)	1.96 (4)	2.736 (6)	153 (7)
O4—H4o⋯O2wⁱ	0.84 (1)	1.81 (3)	2.623 (8)	163 (9)
O5—H5o⋯O2ⁱⁱ	0.84 (1)	1.93 (2)	2.764 (5)	171 (7)
O1w—H1w1⋯O2ⁱⁱⁱ	0.84 (1)	1.98 (2)	2.812 (5)	170 (6)
O1w—H1w2⋯O1ⁱⁱ	0.84 (1)	2.09 (2)	2.914 (6)	167 (6)
O2w—H2w1⋯O3^iv	0.84 (1)	2.13 (5)	2.845 (9)	142 (8)
O2w—H2w2⋯O4^v	0.84 (1)	2.12 (4)	2.900 (8)	154 (8)
Symmetry codes: (i) -x, -y+2, -z+2; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{5\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) -x, -y+3, -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, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022708/bt2751sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808022708/bt2751Isup2.hkl

checkCIF report

Comment top

This study extends the structural study on the Schiff base, 5-bromosalicylaldehyde benzoylhydrazone (Liu et al., 2006) as the title compound (Scheme I, Fig. 1) has several hydroxy groups on one of the aromatic rings. The compound crystallizes with two lattice water molecules. Hydrogen bonding interactions (Table 1) give rise to a layer motif.

Related literature top

For the structure of a similar Schiff-base ligand, 5-bromosalicylaldehyde benzoylhydrazone, see: Liu et al. (2006).

Experimental top

3,4,5-Trihydroxybenzoylhydrazide (0.65 g, 3.5 mmol) and 5-bromo-2-hydroxybenzaldehyde (0.70 g, 3.5 mmol) were heated for 12 h in ethanol. The solvent was removed and the product recrystallized from ethanol.

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, 2008).

Figures top

Fig. 1. View (Barbour, 2001) of N-(5-bromo-2-hydroxybenzylidene)-3,4,5-trihydroxybenzohydrazide with displacement ellipsoids at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

N'-(5-Bromo-2-hydroxybenzylidene)-3,4,5-trihydroxybenzohydrazide dihydrate top

Crystal data top

C₁₄H₁₁BrN₂O₅·2H₂O	F(000) = 816
M_r = 403.19	D_x = 1.779 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2758 reflections
a = 30.8424 (8) Å	θ = 3.2–27.4°
b = 3.7999 (1) Å	µ = 2.77 mm⁻¹
c = 12.8484 (4) Å	T = 100 K
β = 90.280 (2)°	Needle, colorless
V = 1505.79 (7) Å³	0.30 × 0.03 × 0.03 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	3424 independent reflections
Radiation source: fine-focus sealed tube	2914 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ω scans	θ_max = 27.5°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −38→40
T_min = 0.658, T_max = 0.921	k = −4→4
9964 measured reflections	l = −15→16

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.22	w = 1/[σ²(F_o²) + (0.0499P)² + 10.2476P] where P = (F_o² + 2F_c²)/3
3424 reflections	(Δ/σ)_max = 0.001
241 parameters	Δρ_max = 1.08 e Å⁻³
10 restraints	Δρ_min = −1.82 e Å⁻³

Crystal data top

C₁₄H₁₁BrN₂O₅·2H₂O	V = 1505.79 (7) Å³
M_r = 403.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 30.8424 (8) Å	µ = 2.77 mm⁻¹
b = 3.7999 (1) Å	T = 100 K
c = 12.8484 (4) Å	0.30 × 0.03 × 0.03 mm
β = 90.280 (2)°

Data collection top

Bruker SMART APEX diffractometer	3424 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2914 reflections with I > 2σ(I)
T_min = 0.658, T_max = 0.921	R_int = 0.039
9964 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	10 restraints
wR(F²) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.22	w = 1/[σ²(F_o²) + (0.0499P)² + 10.2476P] where P = (F_o² + 2F_c²)/3
3424 reflections	Δρ_max = 1.08 e Å⁻³
241 parameters	Δρ_min = −1.82 e Å⁻³

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
Br1	0.467910 (16)	0.31017 (16)	0.89799 (4)	0.01787 (17)
O1	0.32358 (12)	0.6446 (12)	0.5944 (3)	0.0201 (9)
H1O	0.3020 (15)	0.745 (18)	0.621 (5)	0.030*
O2	0.20078 (11)	0.9755 (11)	0.6545 (3)	0.0182 (8)
O3	0.05472 (13)	1.3768 (13)	0.7962 (4)	0.0295 (11)
H3O	0.0335 (16)	1.36 (2)	0.836 (5)	0.044*
O4	0.05208 (14)	1.1036 (15)	0.9894 (4)	0.0353 (12)
H4O	0.048 (3)	0.933 (15)	1.030 (6)	0.053*
O5	0.12324 (12)	0.7692 (12)	1.0737 (3)	0.0182 (9)
H5O	0.1471 (12)	0.682 (18)	1.092 (5)	0.027*
O1W	0.25912 (12)	1.3152 (13)	0.9988 (3)	0.0209 (9)
H1W1	0.2444 (17)	1.382 (18)	1.050 (3)	0.031*
H1W2	0.2806 (14)	1.199 (17)	1.020 (4)	0.031*
O2W	−0.02887 (15)	1.3435 (17)	0.8657 (5)	0.0506 (16)
H2W1	−0.042 (3)	1.30 (2)	0.810 (4)	0.076*
H2W2	−0.038 (3)	1.534 (14)	0.890 (7)	0.076*
N1	0.27850 (13)	0.8683 (12)	0.7531 (3)	0.0139 (9)
N2	0.24174 (13)	0.9859 (13)	0.8027 (3)	0.0138 (9)
H2N	0.2431	1.0511	0.8684	0.017*
C1	0.35563 (16)	0.5778 (15)	0.6648 (4)	0.0144 (10)
C2	0.39381 (16)	0.4251 (16)	0.6295 (4)	0.0173 (11)
H2	0.3970	0.3730	0.5576	0.021*
C3	0.42746 (17)	0.3479 (16)	0.6985 (4)	0.0193 (12)
H3	0.4535	0.2431	0.6743	0.023*
C4	0.42245 (16)	0.4256 (16)	0.8025 (4)	0.0160 (11)
C5	0.38470 (16)	0.5781 (15)	0.8398 (4)	0.0143 (10)
H5	0.3820	0.6294	0.9118	0.017*
C6	0.35065 (15)	0.6562 (15)	0.7712 (4)	0.0126 (10)
C7	0.31105 (16)	0.7988 (15)	0.8138 (4)	0.0130 (10)
H7	0.3089	0.8415	0.8865	0.016*
C8	0.20343 (16)	1.0010 (13)	0.7503 (4)	0.0108 (10)
C9	0.16507 (16)	1.0460 (15)	0.8180 (4)	0.0130 (10)
C10	0.12793 (16)	1.2046 (16)	0.7771 (4)	0.0163 (11)
H10	0.1281	1.2984	0.7086	0.020*
C11	0.09101 (17)	1.2242 (15)	0.8368 (4)	0.0176 (12)
C12	0.09010 (17)	1.0775 (17)	0.9364 (4)	0.0204 (12)
C13	0.12713 (17)	0.9146 (15)	0.9777 (4)	0.0152 (11)
C14	0.16479 (17)	0.9040 (15)	0.9188 (4)	0.0149 (11)
H14	0.1903	0.8006	0.9468	0.018*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0094 (2)	0.0195 (3)	0.0247 (3)	−0.0001 (2)	−0.00302 (17)	−0.0020 (3)
O1	0.0160 (18)	0.032 (3)	0.0125 (17)	0.0031 (18)	−0.0028 (14)	−0.0016 (17)
O2	0.0127 (17)	0.027 (2)	0.0148 (18)	−0.0039 (16)	−0.0015 (14)	0.0021 (17)
O3	0.0142 (19)	0.041 (3)	0.034 (2)	0.0120 (19)	−0.0051 (17)	−0.005 (2)
O4	0.016 (2)	0.060 (4)	0.030 (2)	0.009 (2)	0.0035 (18)	−0.013 (2)
O5	0.0129 (17)	0.031 (2)	0.0110 (17)	−0.0007 (17)	0.0027 (14)	−0.0045 (16)
O1W	0.0162 (18)	0.035 (2)	0.0113 (17)	0.0027 (18)	0.0015 (14)	−0.0044 (18)
O2W	0.016 (2)	0.049 (4)	0.087 (5)	0.010 (2)	0.010 (2)	0.013 (3)
N1	0.0107 (19)	0.014 (3)	0.017 (2)	−0.0016 (17)	0.0010 (16)	−0.0008 (18)
N2	0.0096 (19)	0.019 (3)	0.013 (2)	−0.0004 (18)	−0.0007 (15)	−0.0028 (18)
C1	0.014 (2)	0.016 (3)	0.014 (2)	−0.002 (2)	−0.0013 (19)	−0.002 (2)
C2	0.013 (2)	0.025 (3)	0.014 (2)	−0.001 (2)	0.0024 (19)	0.000 (2)
C3	0.013 (2)	0.020 (3)	0.025 (3)	0.001 (2)	0.006 (2)	−0.003 (2)
C4	0.012 (2)	0.014 (3)	0.021 (3)	−0.001 (2)	−0.003 (2)	0.003 (2)
C5	0.015 (2)	0.013 (3)	0.015 (2)	−0.001 (2)	0.0005 (19)	−0.002 (2)
C6	0.010 (2)	0.015 (3)	0.013 (2)	−0.003 (2)	0.0008 (18)	0.001 (2)
C7	0.013 (2)	0.015 (3)	0.012 (2)	−0.006 (2)	0.0022 (18)	−0.003 (2)
C8	0.013 (2)	0.004 (3)	0.015 (2)	−0.0007 (18)	−0.0019 (18)	0.0009 (19)
C9	0.011 (2)	0.013 (3)	0.015 (2)	0.000 (2)	−0.0027 (19)	−0.003 (2)
C10	0.013 (2)	0.016 (3)	0.020 (3)	0.001 (2)	−0.0034 (19)	0.000 (2)
C11	0.017 (2)	0.013 (3)	0.022 (3)	0.008 (2)	−0.007 (2)	−0.007 (2)
C12	0.012 (2)	0.027 (3)	0.022 (3)	0.002 (2)	0.001 (2)	−0.012 (2)
C13	0.016 (2)	0.017 (3)	0.013 (2)	0.001 (2)	0.0025 (19)	−0.008 (2)
C14	0.013 (2)	0.016 (3)	0.015 (2)	0.001 (2)	−0.0022 (19)	−0.006 (2)

Geometric parameters (Å, º) top

Br1—C4	1.909 (5)	C1—C6	1.408 (7)
O1—C1	1.361 (6)	C2—C3	1.393 (8)
O1—H1O	0.840 (10)	C2—H2	0.9500
O2—C8	1.236 (6)	C3—C4	1.378 (8)
O3—C11	1.362 (6)	C3—H3	0.9500
O3—H3O	0.838 (10)	C4—C5	1.388 (7)
O4—C12	1.362 (7)	C5—C6	1.400 (7)
O4—H4O	0.840 (10)	C5—H5	0.9500
O5—C13	1.357 (7)	C6—C7	1.446 (7)
O5—H5O	0.841 (10)	C7—H7	0.9500
O1W—H1W1	0.839 (10)	C8—C9	1.482 (7)
O1W—H1W2	0.838 (10)	C9—C10	1.395 (7)
O2W—H2W1	0.838 (10)	C9—C14	1.403 (7)
O2W—H2W2	0.839 (10)	C10—C11	1.378 (7)
N1—C7	1.296 (7)	C10—H10	0.9500
N1—N2	1.378 (6)	C11—C12	1.396 (8)
N2—C8	1.359 (6)	C12—C13	1.401 (8)
N2—H2N	0.8800	C13—C14	1.390 (7)
C1—C2	1.391 (7)	C14—H14	0.9500

C1—O1—H1O	113 (5)	C5—C6—C7	118.3 (4)
C11—O3—H3O	111 (6)	C1—C6—C7	122.9 (5)
C12—O4—H4O	112 (6)	N1—C7—C6	120.1 (4)
C13—O5—H5O	110 (5)	N1—C7—H7	120.0
H1W1—O1W—H1W2	109.6 (18)	C6—C7—H7	120.0
H2W1—O2W—H2W2	109.5 (18)	O2—C8—N2	122.9 (4)
C7—N1—N2	115.1 (4)	O2—C8—C9	123.0 (4)
C8—N2—N1	120.0 (4)	N2—C8—C9	114.1 (4)
C8—N2—H2N	120.0	C10—C9—C14	120.3 (5)
N1—N2—H2N	120.0	C10—C9—C8	119.0 (5)
O1—C1—C2	118.3 (5)	C14—C9—C8	120.4 (5)
O1—C1—C6	121.6 (5)	C11—C10—C9	119.5 (5)
C2—C1—C6	120.1 (5)	C11—C10—H10	120.2
C1—C2—C3	120.6 (5)	C9—C10—H10	120.2
C1—C2—H2	119.7	O3—C11—C10	119.3 (5)
C3—C2—H2	119.7	O3—C11—C12	120.1 (5)
C4—C3—C2	119.1 (5)	C10—C11—C12	120.6 (5)
C4—C3—H3	120.5	O4—C12—C11	116.7 (5)
C2—C3—H3	120.5	O4—C12—C13	123.0 (5)
C3—C4—C5	121.5 (5)	C11—C12—C13	120.3 (5)
C3—C4—Br1	119.2 (4)	O5—C13—C14	124.1 (5)
C5—C4—Br1	119.3 (4)	O5—C13—C12	116.7 (5)
C4—C5—C6	120.0 (5)	C14—C13—C12	119.2 (5)
C4—C5—H5	120.0	C13—C14—C9	120.0 (5)
C6—C5—H5	120.0	C13—C14—H14	120.0
C5—C6—C1	118.7 (5)	C9—C14—H14	120.0

C7—N1—N2—C8	−167.2 (5)	N2—C8—C9—C10	154.0 (5)
O1—C1—C2—C3	−179.3 (5)	O2—C8—C9—C14	147.8 (5)
C6—C1—C2—C3	0.1 (9)	N2—C8—C9—C14	−31.4 (7)
C1—C2—C3—C4	−0.1 (9)	C14—C9—C10—C11	0.6 (9)
C2—C3—C4—C5	0.1 (9)	C8—C9—C10—C11	175.2 (5)
C2—C3—C4—Br1	178.5 (4)	C9—C10—C11—O3	−179.5 (5)
C3—C4—C5—C6	0.0 (9)	C9—C10—C11—C12	−2.0 (9)
Br1—C4—C5—C6	−178.4 (4)	O3—C11—C12—O4	−1.4 (8)
C4—C5—C6—C1	−0.1 (8)	C10—C11—C12—O4	−178.9 (6)
C4—C5—C6—C7	177.0 (5)	O3—C11—C12—C13	178.9 (5)
O1—C1—C6—C5	179.4 (5)	C10—C11—C12—C13	1.4 (9)
C2—C1—C6—C5	0.1 (8)	O4—C12—C13—O5	2.2 (9)
O1—C1—C6—C7	2.5 (9)	C11—C12—C13—O5	−178.1 (5)
C2—C1—C6—C7	−176.9 (5)	O4—C12—C13—C14	−179.1 (6)
N2—N1—C7—C6	176.8 (5)	C11—C12—C13—C14	0.6 (9)
C5—C6—C7—N1	−178.7 (5)	O5—C13—C14—C9	176.7 (5)
C1—C6—C7—N1	−1.8 (8)	C12—C13—C14—C9	−1.9 (8)
N1—N2—C8—O2	−13.6 (8)	C10—C9—C14—C13	1.3 (8)
N1—N2—C8—C9	165.7 (5)	C8—C9—C14—C13	−173.2 (5)
O2—C8—C9—C10	−26.7 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.84 (1)	1.91 (5)	2.616 (6)	141 (7)
O3—H3o···O2w	0.84 (1)	1.96 (4)	2.736 (6)	153 (7)
O4—H4o···O2wⁱ	0.84 (1)	1.81 (3)	2.623 (8)	163 (9)
O5—H5o···O2ⁱⁱ	0.84 (1)	1.93 (2)	2.764 (5)	171 (7)
O1w—H1w1···O2ⁱⁱⁱ	0.84 (1)	1.98 (2)	2.812 (5)	170 (6)
O1w—H1w2···O1ⁱⁱ	0.84 (1)	2.09 (2)	2.914 (6)	167 (6)
O2w—H2w1···O3^iv	0.84 (1)	2.13 (5)	2.845 (9)	142 (8)
O2w—H2w2···O4^v	0.84 (1)	2.12 (4)	2.900 (8)	154 (8)

Symmetry codes: (i) −x, −y+2, −z+2; (ii) x, −y+3/2, z+1/2; (iii) x, −y+5/2, z+1/2; (iv) −x, y−1/2, −z+3/2; (v) −x, −y+3, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁BrN₂O₅·2H₂O
M_r	403.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	30.8424 (8), 3.7999 (1), 12.8484 (4)
β (°)	90.280 (2)
V (Å³)	1505.79 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.77
Crystal size (mm)	0.30 × 0.03 × 0.03

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.658, 0.921
No. of measured, independent and observed [I > 2σ(I)] reflections	9964, 3424, 2914
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.155, 1.22
No. of reflections	3424
No. of parameters	241
No. of restraints	10
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + (0.0499P)² + 10.2476P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.08, −1.82

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.84 (1)	1.91 (5)	2.616 (6)	141 (7)
O3—H3o···O2w	0.84 (1)	1.96 (4)	2.736 (6)	153 (7)
O4—H4o···O2wⁱ	0.84 (1)	1.81 (3)	2.623 (8)	163 (9)
O5—H5o···O2ⁱⁱ	0.84 (1)	1.93 (2)	2.764 (5)	171 (7)
O1w—H1w1···O2ⁱⁱⁱ	0.84 (1)	1.98 (2)	2.812 (5)	170 (6)
O1w—H1w2···O1ⁱⁱ	0.84 (1)	2.09 (2)	2.914 (6)	167 (6)
O2w—H2w1···O3^iv	0.84 (1)	2.13 (5)	2.845 (9)	142 (8)
O2w—H2w2···O4^v	0.84 (1)	2.12 (4)	2.900 (8)	154 (8)

Symmetry codes: (i) −x, −y+2, −z+2; (ii) x, −y+3/2, z+1/2; (iii) x, −y+5/2, z+1/2; (iv) −x, y−1/2, −z+3/2; (v) −x, −y+3, −z+2.

Acknowledgements

We thank the Science Fund (12–02-03–2031, 12–02-03–2051) and the University of Malaya (PJP) for supporting this study. We are grateful to the University of Malaya for the purchase of the diffractometer.

References

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
Liu, H.-Y., Wang, H.-Y., Gao, F., Lu, Z.-S. & Niu, D.-Z. (2006). Acta Cryst. E62, o4495–o4496. Web of Science CSD CrossRef IUCr Journals 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. (2008). publCIF. In preparation. Google Scholar

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Volume 64| Part 8| August 2008| Page o1584

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

N′-(5-Bromo-2-hy­droxy­benzyl­­idene)-3,4,5-tri­hydroxy­benzohydrazide dihydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-(5-Bromo-2-hydroxybenzylidene)-3,4,5-trihydroxybenzohydrazide dihydrate