N′-(3-Bromo-5-chloro-2-hydroxy­benzyl­idene)-3,4,5-trihydroxy­benzohydrazide methanol solvate

Abdul Alhadi, A.A.; Ali, H.M.; Ng, S.W.

doi:10.1107/S1600536809010575

organic compounds

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Volume 65| Part 4| April 2009| Page o909

doi:10.1107/S1600536809010575

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N′-(3-Bromo-5-chloro-2-hydroxybenzylidene)-3,4,5-trihydroxybenzohydrazide methanol solvate

Abeer A. Abdul Alhadi,^a Hapipah Mohd. Ali ^a and Seik Weng Ng ^a ^*

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

(Received 18 March 2009; accepted 23 March 2009; online 28 March 2009)

The benzohydrazide molecule of the title compound, C₁₄H₁₀BrClN₂O₅·CH₃OH, is non-planar, the two aromatic rings at either side of the –C(=O)–NH–N=CH– unit being twisted by 5.9 (1)°. The benzohydrazide molecule is linked to the solvent molecule by an O—H⋯O hydrogen bond. Molecules are connected by further O—H⋯O hydrogen bonds and an N—H⋯O link into a two-dimensional array.

Related literature

For the the parent N′-(2-hydroxybenzylidene)benzohydrazide, see: Lyubchova et al. (1995 ). For other N′-(2-hydroxy-5-nitrobenzylidene)benzohydrazides, see: Ali et al. (2005 ); Lyubchova et al. (1995); Xu & Liu (2006 ).

Experimental

Crystal data

C₁₄H₁₀BrClN₂O₅·CH₄O
M_r = 433.64
Monoclinic, C 2/c
a = 21.6157 (3) Å
b = 12.7408 (2) Å
c = 17.0803 (2) Å
β = 136.641 (1)°
V = 3229.57 (8) Å³
Z = 8
Mo Kα radiation
μ = 2.75 mm⁻¹
T = 123 K
0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.610, T_max = 0.771
15301 measured reflections
3714 independent reflections
3407 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.068
S = 1.03
3714 reflections
251 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O5ⁱ	0.83 (1)	2.03 (3)	2.607 (2)	126 (3)
O3—H3⋯O6ⁱⁱ	0.83 (1)	2.05 (1)	2.856 (2)	165 (3)
O4—H4⋯O1ⁱⁱⁱ	0.83 (1)	2.20 (1)	3.027 (2)	173 (2)
O5—H5⋯O2ⁱⁱⁱ	0.82 (1)	1.79 (1)	2.608 (2)	176 (2)
O6—H6⋯O2	0.83 (1)	2.04 (1)	2.843 (2)	164 (2)
N2—H2⋯O6ⁱⁱⁱ	0.87 (1)	2.25 (1)	3.112 (2)	169 (2)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010575/tk2400sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809010575/tk2400Isup2.hkl

checkCIF report

Related literature top

For the the parent N'-(2-hydroxybenzylidene)benzohydrazide, see: Lyubchova et al. (1995). For other N'-(2-hydroxy-5-nitrobenzylidene)benzohydrazides, see: Ali et al. (2005); Lyubchova et al. (1995); Xu & Liu (2006).

Experimental top

3-Bromo-5-chloro-2-hydroxybenzaldehyde (0.47 g, 2 mmol) and 3,4,5-trihydroxybenzoylhydrazide (0.36 g, 2 mmol) were heated in ethanol (50 ml) for several hours. The solvent was removed and the product recrystallized from methanol.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₁₄H₁₀BrClNO₅^.CH₃OH at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

N'-(3-Bromo-5-chloro-2-hydroxybenzylidene)-3,4,5-trihydroxybenzohydrazide methanol solvate top

Crystal data top

C₁₄H₁₀BrClN₂O₅·CH₄O	F(000) = 1744
M_r = 433.64	D_x = 1.784 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8789 reflections
a = 21.6157 (3) Å	θ = 2.7–28.3°
b = 12.7408 (2) Å	µ = 2.75 mm⁻¹
c = 17.0803 (2) Å	T = 123 K
β = 136.641 (1)°	Polyhedral, tan
V = 3229.57 (8) Å³	0.20 × 0.15 × 0.10 mm
Z = 8

Data collection top

Bruker SMART APEX diffractometer	3714 independent reflections
Radiation source: fine-focus sealed tube	3407 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −28→26
T_min = 0.610, T_max = 0.771	k = −16→16
15301 measured reflections	l = −22→21

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.068	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0429P)² + 3.4447P] where P = (F_o² + 2F_c²)/3
3714 reflections	(Δ/σ)_max = 0.001
251 parameters	Δρ_max = 0.43 e Å⁻³
6 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₄H₁₀BrClN₂O₅·CH₄O	V = 3229.57 (8) Å³
M_r = 433.64	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 21.6157 (3) Å	µ = 2.75 mm⁻¹
b = 12.7408 (2) Å	T = 123 K
c = 17.0803 (2) Å	0.20 × 0.15 × 0.10 mm
β = 136.641 (1)°

Data collection top

Bruker SMART APEX diffractometer	3714 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3407 reflections with I > 2σ(I)
T_min = 0.610, T_max = 0.771	R_int = 0.016
15301 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	6 restraints
wR(F²) = 0.068	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.43 e Å⁻³
3714 reflections	Δρ_min = −0.35 e Å⁻³
251 parameters

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

	x	y	z	U_iso*/U_eq
Br1	0.044783 (12)	0.783092 (13)	0.137916 (14)	0.02172 (7)
Cl1	0.01420 (3)	0.35175 (3)	0.10946 (4)	0.02369 (10)
N1	0.18779 (9)	0.61375 (11)	0.54542 (11)	0.0148 (3)
N2	0.23179 (9)	0.58418 (11)	0.65407 (11)	0.0154 (3)
O1	0.13116 (9)	0.74001 (9)	0.37133 (11)	0.0211 (3)
O2	0.20939 (8)	0.74133 (9)	0.69379 (10)	0.0187 (2)
O3	0.36037 (9)	0.69205 (10)	1.09583 (10)	0.0219 (3)
O4	0.37603 (8)	0.47725 (9)	1.12740 (10)	0.0189 (2)
O5	0.31633 (9)	0.34724 (9)	0.95863 (10)	0.0205 (3)
O6	0.15053 (8)	0.88367 (9)	0.75713 (10)	0.0196 (2)
C1	0.10878 (11)	0.64859 (12)	0.31698 (13)	0.0155 (3)
C2	0.06644 (11)	0.65171 (12)	0.20499 (14)	0.0156 (3)
C3	0.03858 (11)	0.56163 (13)	0.14173 (13)	0.0172 (3)
H3A	0.0088	0.5655	0.0652	0.021*
C4	0.05469 (11)	0.46540 (12)	0.19171 (14)	0.0168 (3)
C5	0.09940 (10)	0.45814 (12)	0.30364 (13)	0.0158 (3)
H5A	0.1117	0.3914	0.3373	0.019*
C6	0.12644 (10)	0.54979 (12)	0.36718 (13)	0.0151 (3)
C7	0.17192 (10)	0.53678 (12)	0.48399 (13)	0.0155 (3)
H7	0.1907	0.4684	0.5163	0.019*
C8	0.23645 (10)	0.64897 (12)	0.72065 (13)	0.0147 (3)
C9	0.27436 (10)	0.60244 (12)	0.82779 (13)	0.0143 (3)
C10	0.30257 (11)	0.66835 (12)	0.91445 (13)	0.0161 (3)
H10	0.2997	0.7424	0.9056	0.019*
C11	0.33473 (11)	0.62583 (12)	1.01356 (13)	0.0156 (3)
C12	0.34227 (10)	0.51690 (12)	1.02835 (13)	0.0146 (3)
C13	0.31234 (10)	0.45163 (12)	0.94055 (13)	0.0147 (3)
C14	0.27745 (10)	0.49359 (12)	0.84020 (13)	0.0146 (3)
H14	0.2557	0.4486	0.7800	0.018*
C15	0.06333 (12)	0.92150 (14)	0.65359 (15)	0.0237 (4)
H15A	0.0445	0.9781	0.6715	0.036*
H15B	0.0196	0.8640	0.6160	0.036*
H15C	0.0664	0.9482	0.6027	0.036*
H1	0.154 (2)	0.731 (3)	0.4365 (15)	0.087 (13)*
H3	0.3635 (18)	0.6613 (19)	1.1413 (18)	0.044 (7)*
H4	0.3783 (17)	0.4119 (8)	1.129 (2)	0.036 (7)*
H5	0.3065 (15)	0.3125 (16)	0.9101 (15)	0.030 (6)*
H6	0.1634 (16)	0.8331 (14)	0.741 (2)	0.037 (7)*
H2	0.2604 (14)	0.5242 (11)	0.6799 (18)	0.029 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02904 (11)	0.01747 (10)	0.01845 (10)	0.00031 (6)	0.01720 (9)	0.00285 (6)
Cl1	0.0373 (2)	0.01580 (19)	0.01895 (19)	−0.00382 (16)	0.02079 (19)	−0.00522 (14)
N1	0.0169 (6)	0.0172 (6)	0.0109 (6)	0.0006 (5)	0.0103 (5)	0.0013 (5)
N2	0.0205 (6)	0.0142 (6)	0.0119 (6)	0.0032 (5)	0.0120 (6)	0.0031 (5)
O1	0.0321 (7)	0.0152 (5)	0.0161 (6)	0.0006 (5)	0.0175 (6)	−0.0016 (5)
O2	0.0293 (6)	0.0135 (5)	0.0186 (6)	0.0039 (5)	0.0191 (5)	0.0034 (4)
O3	0.0374 (7)	0.0154 (5)	0.0171 (6)	−0.0039 (5)	0.0212 (6)	−0.0038 (5)
O4	0.0294 (6)	0.0154 (6)	0.0142 (5)	0.0022 (5)	0.0166 (5)	0.0019 (4)
O5	0.0378 (7)	0.0109 (5)	0.0182 (6)	0.0028 (5)	0.0221 (6)	0.0017 (4)
O6	0.0251 (6)	0.0178 (6)	0.0186 (6)	0.0016 (5)	0.0168 (5)	−0.0013 (5)
C1	0.0184 (7)	0.0151 (7)	0.0154 (7)	−0.0006 (6)	0.0131 (7)	−0.0020 (6)
C2	0.0186 (7)	0.0153 (7)	0.0153 (7)	0.0015 (6)	0.0130 (7)	0.0026 (6)
C3	0.0185 (7)	0.0226 (8)	0.0135 (7)	−0.0012 (6)	0.0126 (7)	−0.0011 (6)
C4	0.0202 (7)	0.0170 (7)	0.0169 (7)	−0.0017 (6)	0.0147 (7)	−0.0037 (6)
C5	0.0184 (7)	0.0153 (7)	0.0164 (7)	0.0005 (6)	0.0136 (6)	0.0007 (6)
C6	0.0164 (7)	0.0182 (7)	0.0129 (7)	0.0004 (6)	0.0113 (6)	0.0003 (6)
C7	0.0173 (7)	0.0156 (7)	0.0135 (7)	0.0006 (6)	0.0112 (6)	0.0017 (6)
C8	0.0165 (7)	0.0151 (7)	0.0138 (7)	−0.0016 (6)	0.0114 (6)	−0.0007 (5)
C9	0.0158 (7)	0.0158 (7)	0.0126 (7)	0.0010 (6)	0.0107 (6)	0.0009 (6)
C10	0.0212 (8)	0.0123 (7)	0.0166 (8)	−0.0005 (6)	0.0144 (7)	−0.0003 (6)
C11	0.0198 (7)	0.0148 (7)	0.0140 (7)	−0.0021 (6)	0.0129 (6)	−0.0030 (6)
C12	0.0168 (7)	0.0167 (7)	0.0123 (7)	0.0009 (6)	0.0112 (6)	0.0013 (6)
C13	0.0180 (7)	0.0121 (7)	0.0168 (7)	0.0016 (6)	0.0136 (6)	0.0006 (6)
C14	0.0189 (7)	0.0136 (7)	0.0144 (7)	0.0005 (6)	0.0131 (6)	−0.0005 (5)
C15	0.0247 (8)	0.0219 (8)	0.0214 (8)	0.0000 (7)	0.0158 (7)	−0.0015 (7)

Geometric parameters (Å, º) top

Br1—C2	1.8852 (15)	C3—C4	1.386 (2)
Cl1—C4	1.7460 (16)	C3—H3A	0.9500
N1—C7	1.287 (2)	C4—C5	1.382 (2)
N1—N2	1.3870 (18)	C5—C6	1.400 (2)
N2—C8	1.348 (2)	C5—H5A	0.9500
N2—H2	0.874 (10)	C6—C7	1.457 (2)
O1—C1	1.3415 (19)	C7—H7	0.9500
O1—H1	0.832 (10)	C8—C9	1.480 (2)
O2—C8	1.2438 (19)	C9—C14	1.397 (2)
O3—C11	1.3642 (19)	C9—C10	1.398 (2)
O3—H3	0.828 (10)	C10—C11	1.390 (2)
O4—C12	1.3619 (18)	C10—H10	0.9500
O4—H4	0.833 (10)	C11—C12	1.399 (2)
O5—C13	1.3538 (18)	C12—C13	1.396 (2)
O5—H5	0.820 (10)	C13—C14	1.383 (2)
O6—C15	1.437 (2)	C14—H14	0.9500
O6—H6	0.828 (10)	C15—H15A	0.9800
C1—C2	1.397 (2)	C15—H15B	0.9800
C1—C6	1.410 (2)	C15—H15C	0.9800
C2—C3	1.379 (2)

C7—N1—N2	113.63 (13)	C6—C7—H7	118.5
C8—N2—N1	121.35 (13)	O2—C8—N2	122.77 (14)
C8—N2—H2	121.2 (15)	O2—C8—C9	121.61 (14)
N1—N2—H2	117.2 (15)	N2—C8—C9	115.61 (13)
C1—O1—H1	112 (3)	C14—C9—C10	119.97 (14)
C11—O3—H3	111.6 (19)	C14—C9—C8	120.49 (14)
C12—O4—H4	112.6 (18)	C10—C9—C8	119.44 (14)
C13—O5—H5	111.9 (17)	C11—C10—C9	120.15 (14)
C15—O6—H6	107.8 (17)	C11—C10—H10	119.9
O1—C1—C2	118.05 (14)	C9—C10—H10	119.9
O1—C1—C6	123.52 (14)	O3—C11—C10	118.85 (14)
C2—C1—C6	118.42 (14)	O3—C11—C12	121.39 (14)
C3—C2—C1	121.82 (14)	C10—C11—C12	119.75 (14)
C3—C2—Br1	119.27 (12)	O4—C12—C13	121.65 (14)
C1—C2—Br1	118.90 (12)	O4—C12—C11	118.63 (14)
C2—C3—C4	118.86 (14)	C13—C12—C11	119.67 (14)
C2—C3—H3A	120.6	O5—C13—C14	123.32 (14)
C4—C3—H3A	120.6	O5—C13—C12	115.94 (14)
C5—C4—C3	121.40 (14)	C14—C13—C12	120.69 (14)
C5—C4—Cl1	119.65 (12)	C13—C14—C9	119.64 (14)
C3—C4—Cl1	118.92 (12)	C13—C14—H14	120.2
C4—C5—C6	119.62 (14)	C9—C14—H14	120.2
C4—C5—H5A	120.2	O6—C15—H15A	109.5
C6—C5—H5A	120.2	O6—C15—H15B	109.5
C5—C6—C1	119.81 (14)	H15A—C15—H15B	109.5
C5—C6—C7	116.89 (14)	O6—C15—H15C	109.5
C1—C6—C7	123.30 (14)	H15A—C15—H15C	109.5
N1—C7—C6	122.97 (14)	H15B—C15—H15C	109.5
N1—C7—H7	118.5

C7—N1—N2—C8	−165.52 (15)	N1—N2—C8—C9	172.04 (14)
O1—C1—C2—C3	−177.88 (15)	O2—C8—C9—C14	159.38 (15)
C6—C1—C2—C3	2.7 (2)	N2—C8—C9—C14	−19.4 (2)
O1—C1—C2—Br1	0.8 (2)	O2—C8—C9—C10	−17.1 (2)
C6—C1—C2—Br1	−178.63 (11)	N2—C8—C9—C10	164.18 (15)
C1—C2—C3—C4	−1.2 (2)	C14—C9—C10—C11	0.8 (2)
Br1—C2—C3—C4	−179.92 (12)	C8—C9—C10—C11	177.25 (14)
C2—C3—C4—C5	−1.3 (2)	C9—C10—C11—O3	−178.92 (15)
C2—C3—C4—Cl1	176.64 (12)	C9—C10—C11—C12	2.6 (2)
C3—C4—C5—C6	2.2 (2)	O3—C11—C12—O4	0.0 (2)
Cl1—C4—C5—C6	−175.66 (12)	C10—C11—C12—O4	178.42 (14)
C4—C5—C6—C1	−0.7 (2)	O3—C11—C12—C13	177.72 (14)
C4—C5—C6—C7	179.02 (14)	C10—C11—C12—C13	−3.9 (2)
O1—C1—C6—C5	178.92 (15)	O4—C12—C13—O5	2.0 (2)
C2—C1—C6—C5	−1.7 (2)	C11—C12—C13—O5	−175.63 (14)
O1—C1—C6—C7	−0.8 (2)	O4—C12—C13—C14	179.35 (14)
C2—C1—C6—C7	178.61 (14)	C11—C12—C13—C14	1.7 (2)
N2—N1—C7—C6	−179.99 (14)	O5—C13—C14—C9	178.84 (15)
C5—C6—C7—N1	−169.07 (15)	C12—C13—C14—C9	1.7 (2)
C1—C6—C7—N1	10.7 (2)	C10—C9—C14—C13	−3.0 (2)
N1—N2—C8—O2	−6.7 (2)	C8—C9—C14—C13	−179.38 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5ⁱ	0.83 (1)	2.03 (3)	2.607 (2)	126 (3)
O3—H3···O6ⁱⁱ	0.83 (1)	2.05 (1)	2.856 (2)	165 (3)
O4—H4···O1ⁱⁱⁱ	0.83 (1)	2.20 (1)	3.027 (2)	173 (2)
O5—H5···O2ⁱⁱⁱ	0.82 (1)	1.79 (1)	2.608 (2)	176 (2)
O6—H6···O2	0.83 (1)	2.04 (1)	2.843 (2)	164 (2)
N2—H2···O6ⁱⁱⁱ	0.87 (1)	2.25 (1)	3.112 (2)	169 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀BrClN₂O₅·CH₄O
M_r	433.64
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	123
a, b, c (Å)	21.6157 (3), 12.7408 (2), 17.0803 (2)
β (°)	136.641 (1)
V (Å³)	3229.57 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.75
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.610, 0.771
No. of measured, independent and observed [I > 2σ(I)] reflections	15301, 3714, 3407
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.068, 1.03
No. of reflections	3714
No. of parameters	251
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.35

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5ⁱ	0.83 (1)	2.03 (3)	2.607 (2)	126 (3)
O3—H3···O6ⁱⁱ	0.83 (1)	2.05 (1)	2.856 (2)	165 (3)
O4—H4···O1ⁱⁱⁱ	0.83 (1)	2.20 (1)	3.027 (2)	173 (2)
O5—H5···O2ⁱⁱⁱ	0.82 (1)	1.79 (1)	2.608 (2)	176 (2)
O6—H6···O2	0.83 (1)	2.04 (1)	2.843 (2)	164 (2)
N2—H2···O6ⁱⁱⁱ	0.87 (1)	2.25 (1)	3.112 (2)	169 (2)

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

Acknowledgements

We thank the University of Malaya for supporting this study.

References

Ali, H. M., Puvaneswary, S. & Ng, S. W. (2005). Acta Cryst. E61, o3464–o3465. Web of Science CSD CrossRef IUCr Journals Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lyubchova, A., Cossé-Barbi, A., Doucet, J. P., Robert, F., Souron, J.-P. & Quarton, M. (1995). Acta Cryst. C51, 1893–1895. CSD CrossRef CAS Web of Science 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. (2009). publCIF. In preparation. Google Scholar
Xu, H.-M. & Liu, S.-X. (2006). Acta Cryst. E62, o3026–o3027. Web of Science CSD 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′-(3-Bromo-5-chloro-2-hy­droxy­benzyl­­idene)-3,4,5-tri­hydroxy­benzohydrazide methanol solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-(3-Bromo-5-chloro-2-hydroxybenzylidene)-3,4,5-trihydroxybenzohydrazide methanol solvate