N′-(2,4-Dimethoxy­benzyl­idene)-3,4,5-trihydroxy­benzohydrazide ethanol solvate

Alhadi, A.A.; Saharin, S.M.; Mohd Ali, H.; Robinson, W.T.; Abdulla, M.A.

doi:10.1107/S1600536809018947

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1373

doi:10.1107/S1600536809018947

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N′-(2,4-Dimethoxybenzylidene)-3,4,5-trihydroxybenzohydrazide ethanol solvate

Abeer A. Alhadi,^a Siti Munirah Saharin,^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: hapipah@um.edu.my

(Received 30 April 2009; accepted 19 May 2009; online 23 May 2009)

The title compound, C₁₆H₁₆N₂O₆·C₂H₅OH, was synthesized from 3,4,5-trihydroxybenzoylhydrazide and 2,4-dimethoxybenzaldehyde in ethanol. The compound is not planar, with the two aromatic planes of the two aromatic rings twisted by 15.6 (1)°. The hydroxy groups are involved in both intramolecular O—H⋯O and intermolecular O—H⋯N and O—H⋯O hydrogen bonds and a C—H⋯O interaction also occurs.

Related literature

For related compounds, see Abdul Alhadi et al. (2009 ). For the parent N′-(2-hydroxybenzylidene)benzohydrazide, see Lyubchova et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₆N₂O₆·C₂H₆O
M_r = 378.38
Monoclinic, P 2₁ /n
a = 7.8347 (1) Å
b = 17.5412 (3) Å
c = 13.0230 (2) Å
β = 93.936 (1)°
V = 1785.53 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.31 × 0.16 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.967, T_max = 0.987
19580 measured reflections
5188 independent reflections
3586 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.121
S = 1.02
5188 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.84	2.54	2.9325 (13)	109
O3—H3⋯O2	0.84	2.54	2.9325 (13)	110
O4—H4⋯O3	0.84	2.25	2.7009 (14)	114
N1—H1′⋯O7ⁱ	0.88	2.04	2.8844 (15)	160
O2—H2⋯O1ⁱⁱ	0.84	1.86	2.6871 (13)	170
O2—H2⋯N2ⁱⁱ	0.84	2.57	2.9293 (15)	107
O3—H3⋯O1ⁱⁱ	0.84	1.88	2.7200 (13)	177
O4—H4⋯O6ⁱⁱⁱ	0.84	2.14	2.7366 (14)	127
C14—H14⋯O2^iv	0.95	2.42	3.3539 (17)	167
Symmetry codes: (i) x, y-1, z; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x+1, y, z+1; (iv) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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 I, global. DOI: 10.1107/S1600536809018947/hg2510sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809018947/hg2510Isup2.hkl

checkCIF report

Related literature top

For related compounds, see Abdul Alhadi et al. (2009). For the parent N'-(2-hydroxybenzylidene)benzohydrazide, see Lyubchova et al. (1995).

Experimental top

A mixture of 3,4,5-trihydroxybenzoylhydrazide and 2,4-dimethoxybenzaldehyde were heated in ethanol (50 ml) for 12 h. The yellow crystals were obtained by recrystallization 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. Thermal ellipsoid plot (Barbour, 2001) of C₁₆H₁₆N₂O₆.C₂H₅OH at 70% probability level. Hydrogen atoms are drawn as sphere of arbitrary radius.

N'-(2,4-Dimethoxybenzylidene)-3,4,5-trihydroxybenzohydrazide ethanol solvate top

Crystal data top

C₁₆H₁₆N₂O₆·C₂H₆O	F(000) = 800
M_r = 378.38	D_x = 1.408 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3445 reflections
a = 7.8347 (1) Å	θ = 2.8–29.1°
b = 17.5412 (3) Å	µ = 0.11 mm⁻¹
c = 13.0230 (2) Å	T = 100 K
β = 93.936 (1)°	Block, yellow
V = 1785.53 (5) Å³	0.31 × 0.16 × 0.12 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	5188 independent reflections
Radiation source: fine-focus sealed tube	3586 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ω scans	θ_max = 30.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
T_min = 0.967, T_max = 0.987	k = −24→24
19580 measured reflections	l = −18→18

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0566P)² + 0.3538P] where P = (F_o² + 2F_c²)/3
5188 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₆H₁₆N₂O₆·C₂H₆O	V = 1785.53 (5) Å³
M_r = 378.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.8347 (1) Å	µ = 0.11 mm⁻¹
b = 17.5412 (3) Å	T = 100 K
c = 13.0230 (2) Å	0.31 × 0.16 × 0.12 mm
β = 93.936 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5188 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3586 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.987	R_int = 0.041
19580 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.02	Δρ_max = 0.41 e Å⁻³
5188 reflections	Δρ_min = −0.27 e Å⁻³
253 parameters

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.

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
C1	1.15941 (17)	0.21466 (7)	0.76768 (10)	0.0156 (3)
H1	1.1458	0.2583	0.7248	0.019*
C2	1.25203 (17)	0.22016 (7)	0.86245 (10)	0.0153 (3)
C3	1.26837 (17)	0.15678 (8)	0.92716 (10)	0.0154 (3)
C4	1.19696 (18)	0.08744 (8)	0.89317 (10)	0.0170 (3)
C5	1.10756 (18)	0.08150 (8)	0.79830 (10)	0.0176 (3)
H5	1.0605	0.0339	0.7760	0.021*
C6	1.08672 (17)	0.14571 (7)	0.73529 (10)	0.0154 (3)
C7	0.98683 (17)	0.14395 (8)	0.63409 (10)	0.0159 (3)
C8	0.74521 (17)	0.00842 (8)	0.49550 (10)	0.0168 (3)
H8	0.7539	−0.0296	0.5476	0.023 (4)*
C9	0.64100 (17)	−0.00596 (8)	0.40063 (10)	0.0165 (3)
C10	0.57036 (17)	−0.07846 (8)	0.38154 (10)	0.0163 (3)
C11	0.47202 (17)	−0.09404 (8)	0.29061 (10)	0.0172 (3)
H11	0.4236	−0.1431	0.2785	0.021*
C12	0.44633 (18)	−0.03640 (8)	0.21828 (11)	0.0188 (3)
C13	0.51352 (19)	0.03637 (8)	0.23587 (11)	0.0209 (3)
H13	0.4939	0.0754	0.1859	0.025*
C14	0.60860 (18)	0.05093 (8)	0.32640 (11)	0.0190 (3)
H14	0.6533	0.1007	0.3389	0.023*
C15	0.2879 (2)	−0.11915 (8)	0.09897 (11)	0.0227 (3)
H15A	0.3824	−0.1557	0.0978	0.034*
H15B	0.2270	−0.1169	0.0307	0.034*
H15C	0.2087	−0.1354	0.1498	0.034*
C16	0.5321 (2)	−0.20516 (8)	0.44383 (12)	0.0247 (3)
H16A	0.4072	−0.2007	0.4358	0.037*
H16B	0.5647	−0.2364	0.5044	0.037*
H16C	0.5737	−0.2292	0.3824	0.037*
C17	0.7901 (2)	0.81507 (9)	0.72385 (14)	0.0313 (4)
H19A	0.6929	0.8370	0.6826	0.047*
H19B	0.7482	0.7866	0.7818	0.047*
H19C	0.8531	0.7806	0.6809	0.047*
C18	0.9073 (2)	0.87827 (9)	0.76416 (12)	0.0259 (3)
H18A	0.8458	0.9110	0.8113	0.031*
H18B	1.0074	0.8559	0.8038	0.031*
N1	0.92094 (15)	0.07647 (6)	0.60343 (9)	0.0168 (2)
H1'	0.9379	0.0357	0.6422	0.030 (5)*
N2	0.82556 (15)	0.07168 (6)	0.50974 (9)	0.0174 (2)
O1	0.96209 (13)	0.20261 (5)	0.58110 (7)	0.0219 (2)
O2	1.32670 (14)	0.28879 (5)	0.88620 (7)	0.0218 (2)
H2	1.3569	0.2901	0.9493	0.033*
O3	1.35316 (13)	0.15568 (6)	1.02261 (7)	0.0209 (2)
H3	1.3877	0.1998	1.0381	0.031*
O4	1.21299 (15)	0.02350 (6)	0.95174 (8)	0.0273 (3)
H4	1.2718	0.0332	1.0065	0.041*
O5	0.60584 (13)	−0.13118 (6)	0.45673 (7)	0.0224 (2)
O6	0.35424 (14)	−0.04532 (6)	0.12604 (8)	0.0264 (3)
O7	0.96498 (14)	0.92367 (6)	0.68270 (8)	0.0229 (2)
H7	1.0291	0.8975	0.6475	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0190 (6)	0.0138 (6)	0.0137 (6)	0.0025 (5)	−0.0015 (5)	0.0010 (5)
C2	0.0187 (6)	0.0123 (6)	0.0148 (6)	−0.0006 (5)	0.0000 (5)	−0.0015 (5)
C3	0.0175 (6)	0.0163 (6)	0.0119 (6)	0.0006 (5)	−0.0021 (5)	−0.0010 (5)
C4	0.0214 (7)	0.0143 (6)	0.0147 (6)	0.0000 (5)	−0.0029 (5)	0.0027 (5)
C5	0.0223 (7)	0.0140 (6)	0.0159 (7)	−0.0007 (5)	−0.0034 (5)	−0.0003 (5)
C6	0.0171 (6)	0.0156 (6)	0.0131 (6)	0.0011 (5)	−0.0020 (5)	−0.0006 (5)
C7	0.0175 (6)	0.0157 (6)	0.0141 (6)	0.0019 (5)	−0.0016 (5)	−0.0005 (5)
C8	0.0194 (7)	0.0158 (6)	0.0148 (6)	0.0008 (5)	−0.0021 (5)	0.0007 (5)
C9	0.0170 (6)	0.0168 (6)	0.0151 (7)	−0.0002 (5)	−0.0021 (5)	−0.0009 (5)
C10	0.0187 (7)	0.0162 (6)	0.0139 (6)	0.0010 (5)	−0.0010 (5)	0.0013 (5)
C11	0.0188 (7)	0.0162 (6)	0.0161 (6)	−0.0014 (5)	−0.0020 (5)	−0.0015 (5)
C12	0.0201 (7)	0.0192 (7)	0.0162 (7)	0.0000 (5)	−0.0059 (5)	−0.0012 (5)
C13	0.0274 (8)	0.0156 (6)	0.0186 (7)	−0.0001 (6)	−0.0065 (6)	0.0026 (5)
C14	0.0208 (7)	0.0141 (6)	0.0212 (7)	−0.0009 (5)	−0.0040 (5)	−0.0008 (5)
C15	0.0287 (8)	0.0186 (7)	0.0197 (7)	−0.0034 (6)	−0.0074 (6)	−0.0025 (6)
C16	0.0339 (8)	0.0158 (7)	0.0236 (8)	−0.0045 (6)	−0.0042 (6)	0.0033 (6)
C17	0.0369 (9)	0.0197 (7)	0.0381 (10)	−0.0044 (7)	0.0079 (7)	−0.0009 (7)
C18	0.0344 (8)	0.0217 (7)	0.0212 (7)	0.0002 (6)	−0.0020 (6)	0.0049 (6)
N1	0.0215 (6)	0.0151 (5)	0.0129 (5)	−0.0010 (4)	−0.0063 (4)	0.0013 (4)
N2	0.0199 (6)	0.0172 (6)	0.0142 (6)	0.0000 (5)	−0.0064 (4)	−0.0011 (4)
O1	0.0323 (6)	0.0142 (5)	0.0176 (5)	0.0012 (4)	−0.0101 (4)	0.0016 (4)
O2	0.0353 (6)	0.0145 (5)	0.0145 (5)	−0.0057 (4)	−0.0070 (4)	0.0012 (4)
O3	0.0310 (6)	0.0167 (5)	0.0137 (5)	−0.0028 (4)	−0.0079 (4)	0.0011 (4)
O4	0.0446 (7)	0.0167 (5)	0.0184 (5)	−0.0065 (5)	−0.0141 (5)	0.0056 (4)
O5	0.0320 (6)	0.0162 (5)	0.0177 (5)	−0.0042 (4)	−0.0076 (4)	0.0030 (4)
O6	0.0382 (6)	0.0176 (5)	0.0209 (5)	−0.0043 (4)	−0.0160 (5)	0.0010 (4)
O7	0.0295 (6)	0.0163 (5)	0.0232 (6)	0.0001 (4)	0.0034 (4)	−0.0001 (4)

Geometric parameters (Å, º) top

C1—C6	1.3900 (18)	C13—C14	1.3745 (19)
C1—C2	1.3914 (18)	C13—H13	0.9500
C1—H1	0.9500	C14—H14	0.9500
C2—O2	1.3647 (15)	C15—O6	1.4308 (16)
C2—C3	1.3958 (18)	C15—H15A	0.9800
C3—O3	1.3687 (15)	C15—H15B	0.9800
C3—C4	1.3979 (18)	C15—H15C	0.9800
C4—O4	1.3574 (16)	C16—O5	1.4258 (17)
C4—C5	1.3818 (18)	C16—H16A	0.9800
C5—C6	1.3965 (18)	C16—H16B	0.9800
C5—H5	0.9500	C16—H16C	0.9800
C6—C7	1.4862 (18)	C17—C18	1.511 (2)
C7—O1	1.2466 (16)	C17—H19A	0.9800
C7—N1	1.3412 (17)	C17—H19B	0.9800
C8—N2	1.2830 (17)	C17—H19C	0.9800
C8—C9	1.4554 (18)	C18—O7	1.4247 (18)
C8—H8	0.9500	C18—H18A	0.9900
C9—C14	1.4004 (19)	C18—H18B	0.9900
C9—C10	1.4023 (18)	N1—N2	1.3889 (15)
C10—O5	1.3615 (16)	N1—H1'	0.8800
C10—C11	1.3948 (18)	O2—H2	0.8400
C11—C12	1.3869 (19)	O3—H3	0.8400
C11—H11	0.9500	O4—H4	0.8400
C12—O6	1.3672 (16)	O7—H7	0.8400
C12—C13	1.3938 (19)

C6—C1—C2	120.50 (12)	C12—C13—H13	120.4
C6—C1—H1	119.8	C13—C14—C9	121.44 (13)
C2—C1—H1	119.8	C13—C14—H14	119.3
O2—C2—C1	116.85 (12)	C9—C14—H14	119.3
O2—C2—C3	123.07 (11)	O6—C15—H15A	109.5
C1—C2—C3	120.06 (12)	O6—C15—H15B	109.5
O3—C3—C2	125.32 (12)	H15A—C15—H15B	109.5
O3—C3—C4	115.73 (11)	O6—C15—H15C	109.5
C2—C3—C4	118.93 (11)	H15A—C15—H15C	109.5
O4—C4—C5	117.51 (12)	H15B—C15—H15C	109.5
O4—C4—C3	121.43 (12)	O5—C16—H16A	109.5
C5—C4—C3	121.07 (12)	O5—C16—H16B	109.5
C4—C5—C6	119.75 (12)	H16A—C16—H16B	109.5
C4—C5—H5	120.1	O5—C16—H16C	109.5
C6—C5—H5	120.1	H16A—C16—H16C	109.5
C1—C6—C5	119.63 (12)	H16B—C16—H16C	109.5
C1—C6—C7	117.84 (11)	C18—C17—H19A	109.5
C5—C6—C7	122.52 (12)	C18—C17—H19B	109.5
O1—C7—N1	121.44 (12)	H19A—C17—H19B	109.5
O1—C7—C6	121.75 (12)	C18—C17—H19C	109.5
N1—C7—C6	116.79 (12)	H19A—C17—H19C	109.5
N2—C8—C9	120.91 (12)	H19B—C17—H19C	109.5
N2—C8—H8	119.5	O7—C18—C17	111.58 (13)
C9—C8—H8	119.5	O7—C18—H18A	109.3
C14—C9—C10	118.24 (12)	C17—C18—H18A	109.3
C14—C9—C8	121.81 (12)	O7—C18—H18B	109.3
C10—C9—C8	119.95 (12)	C17—C18—H18B	109.3
O5—C10—C11	123.45 (12)	H18A—C18—H18B	108.0
O5—C10—C9	115.45 (11)	C7—N1—N2	119.19 (11)
C11—C10—C9	121.09 (12)	C7—N1—H1'	120.4
C12—C11—C10	118.67 (12)	N2—N1—H1'	120.4
C12—C11—H11	120.7	C8—N2—N1	114.10 (11)
C10—C11—H11	120.7	C2—O2—H2	109.5
O6—C12—C11	123.82 (12)	C3—O3—H3	109.5
O6—C12—C13	114.82 (12)	C4—O4—H4	109.5
C11—C12—C13	121.36 (12)	C10—O5—C16	118.18 (11)
C14—C13—C12	119.17 (13)	C12—O6—C15	118.75 (11)
C14—C13—H13	120.4	C18—O7—H7	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.84	2.54	2.9325 (13)	109
O3—H3···O2	0.84	2.54	2.9325 (13)	110
O4—H4···O3	0.84	2.25	2.7009 (14)	114
N1—H1′···O7ⁱ	0.88	2.04	2.8844 (15)	160
O2—H2···O1ⁱⁱ	0.84	1.86	2.6871 (13)	170
O2—H2···N2ⁱⁱ	0.84	2.57	2.9293 (15)	107
O3—H3···O1ⁱⁱ	0.84	1.88	2.7200 (13)	177
O4—H4···O6ⁱⁱⁱ	0.84	2.14	2.7366 (14)	127
C14—H14···O2^iv	0.95	2.42	3.3539 (17)	167

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O₆·C₂H₆O
M_r	378.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	7.8347 (1), 17.5412 (3), 13.0230 (2)
β (°)	93.936 (1)
V (Å³)	1785.53 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.31 × 0.16 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.967, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	19580, 5188, 3586
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.714

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.121, 1.02
No. of reflections	5188
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.27

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
O2—H2···O3	0.84	2.54	2.9325 (13)	109.4
O3—H3···O2	0.84	2.54	2.9325 (13)	109.8
O4—H4···O3	0.84	2.25	2.7009 (14)	114.2
N1—H1'···O7ⁱ	0.88	2.04	2.8844 (15)	160
O2—H2···O1ⁱⁱ	0.84	1.86	2.6871 (13)	169.7
O2—H2···N2ⁱⁱ	0.84	2.57	2.9293 (15)	107.4
O3—H3···O1ⁱⁱ	0.84	1.88	2.7200 (13)	176.5
O4—H4···O6ⁱⁱⁱ	0.84	2.14	2.7366 (14)	127.3
C14—H14···O2^iv	0.95	2.42	3.3539 (17)	166.5

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

Acknowledgements

The authors thank the University of Malaya for funding this study (Science Fund Grant 12-0-03-2031, 12-02-03-2051 and PJP FS350-2008)

References

Abdul Alhadi, A. A., Ali, H. M. & Ng, S. W. (2009). Acta Cryst. E65, o909. Web of Science CSD CrossRef IUCr Journals 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
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. (2008). publCIF. In preparation. Google Scholar

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Volume 65| Part 6| June 2009| Page o1373

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

N′-(2,4-Di­meth­oxy­benzyl­­idene)-3,4,5-tri­hydroxy­benzohydrazide ethanol solvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-(2,4-Dimethoxybenzylidene)-3,4,5-trihydroxybenzohydrazide ethanol solvate