Bis[4-hydr­oxy-N′-(4-meth­oxy-2-oxido­benzyl­idene-κO2)benzohydrazidato-κ2O,N′]cadmium(II) dimethyl sulfoxide disolvate

Mohd Lair, N.; Mohd Ali, H.; Ng, S.W.

doi:10.1107/S1600536809013774

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page m541

doi:10.1107/S1600536809013774

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Bis[4-hydroxy-N′-(4-methoxy-2-oxidobenzylidene-κO²)benzohydrazidato-κ²O,N′]cadmium(II) dimethyl sulfoxide disolvate

Nooraziah Mohd Lair,^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 12 April 2009; accepted 13 April 2009; online 22 April 2009)

The metal atom in the title compound, [Cd(C₁₅H₁₃N₂O₄)₂]·2C₂H₆OS, is twice O,N,O′-chelated by two symmetry-related Schiff base ligands to define a trans-N₂O₄ octahedral geometry. Each anion occupies meridional sites of the octahedron; the metal atom lies on a special position of site symmetry 2. The dimethyl sulfoxide molecule is a hydrogen-bond acceptor to the –NH– unit, and O—H⋯O hydrogen bonds link molecules into a supramolecular chain.

Related literature

For the monohydrated Schiff base ligand, see: Mohd Lair et al. (2009 ).

Experimental

Crystal data

[Cd(C₁₅H₁₃N₂O₄)₂]·2C₂H₆OS
M_r = 839.20
Monoclinic, C 2/c
a = 23.891 (2) Å
b = 10.439 (1) Å
c = 19.874 (1) Å
β = 132.137 (4)°
V = 3675.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.77 mm⁻¹
T = 118 K
0.12 × 0.06 × 0.03 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.507, T_max = 0.745 (expected range = 0.665–0.977)
10208 measured reflections
3243 independent reflections
2147 reflections with I > 2σ(I)
R_int = 0.103

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.153
S = 1.02
3243 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 1.31 e Å⁻³
Δρ_min = −0.90 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O1ⁱ	0.84	1.79	2.603 (6)	163
N2—H2⋯O5	0.88	1.93	2.766 (6)	159
Symmetry code: (i) $[x, -y+1, z+{\script{1\over 2}}]$ .

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/S1600536809013774/tk2421sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809013774/tk2421Isup2.hkl

checkCIF report

Related literature top

For the monohydrated Schiff base ligand, see: Mohd Lair et al. (2009).

Experimental top

4-Hydroxy-N'-(2-hydroxy-4-methoxybenzylidene)benzohydrazide monohydrate (0.30 g, 1 mmol) and cadmium diacetate (0.14 g, 0.5 mmol) were heated in ethanol (50 ml) for 4 h. The solvent was removed and the product was recrystallized from DMSO to give prismatic crystals.

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 Cd(C₁₅H₁₃N₂O₄)₂^.2DMSO at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Bis[4-hydroxy-N'-(4-methoxy-2-oxidobenzylidene- κO²)benzohydrazidato-κ²O,N']cadmium(II) dimethyl sulfoxide disolvate top

Crystal data top

[Cd(C₁₅H₁₃N₂O₄)₂]·2C₂H₆OS	F(000) = 1720
M_r = 839.20	D_x = 1.517 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 638 reflections
a = 23.891 (2) Å	θ = 2.2–18.8°
b = 10.439 (1) Å	µ = 0.77 mm⁻¹
c = 19.874 (1) Å	T = 118 K
β = 132.137 (4)°	Prism, yellow
V = 3675.3 (4) Å³	0.12 × 0.06 × 0.03 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	3243 independent reflections
Radiation source: fine-focus sealed tube	2147 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.103
ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −28→28
T_min = 0.507, T_max = 0.745	k = −12→12
10208 measured reflections	l = −23→23

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0692P)² + 0.0136P] where P = (F_o² + 2F_c²)/3
3243 reflections	(Δ/σ)_max = 0.001
211 parameters	Δρ_max = 1.31 e Å⁻³
0 restraints	Δρ_min = −0.90 e Å⁻³

Crystal data top

[Cd(C₁₅H₁₃N₂O₄)₂]·2C₂H₆OS	V = 3675.3 (4) Å³
M_r = 839.20	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 23.891 (2) Å	µ = 0.77 mm⁻¹
b = 10.439 (1) Å	T = 118 K
c = 19.874 (1) Å	0.12 × 0.06 × 0.03 mm
β = 132.137 (4)°

Data collection top

Bruker SMART APEX diffractometer	3243 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2147 reflections with I > 2σ(I)
T_min = 0.507, T_max = 0.745	R_int = 0.103
10208 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.02	Δρ_max = 1.31 e Å⁻³
3243 reflections	Δρ_min = −0.90 e Å⁻³
211 parameters

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

	x	y	z	U_iso*/U_eq
Cd1	0.5000	0.32500 (7)	0.7500	0.0253 (2)
S1	0.18289 (10)	0.48574 (18)	0.67220 (12)	0.0335 (5)
O1	0.4272 (2)	0.1893 (4)	0.6323 (3)	0.0276 (10)
O2	0.2426 (3)	−0.1133 (5)	0.4273 (3)	0.0373 (12)
O3	0.5137 (2)	0.4972 (4)	0.8391 (3)	0.0264 (10)
O4	0.4911 (2)	0.8669 (4)	1.0697 (3)	0.0304 (11)
H4	0.4624	0.8507	1.0791	0.046*
N1	0.3944 (3)	0.3437 (5)	0.7273 (3)	0.0227 (12)
N2	0.3971 (3)	0.4373 (5)	0.7788 (4)	0.0262 (13)
H2	0.3589	0.4493	0.7755	0.031*
O5	0.2603 (2)	0.4283 (5)	0.7353 (4)	0.0432 (13)
C1	0.35890 (17)	0.1366 (4)	0.5922 (3)	0.0261 (16)
C2	0.3336 (2)	0.0367 (4)	0.5313 (3)	0.0291 (16)
H2A	0.3643	0.0060	0.5204	0.035*
C3	0.2633 (2)	−0.0181 (4)	0.4865 (3)	0.0295 (16)
C4	0.21840 (18)	0.0268 (4)	0.5025 (3)	0.0339 (17)
H4A	0.1704	−0.0107	0.4719	0.041*
C5	0.2437 (2)	0.1267 (4)	0.5634 (3)	0.0326 (17)
H5	0.2130	0.1574	0.5743	0.039*
C6	0.3140 (2)	0.1815 (4)	0.6082 (3)	0.0286 (15)
C7	0.1732 (4)	−0.1797 (8)	0.3856 (5)	0.0438 (19)
H7A	0.1662	−0.2488	0.3471	0.066*
H7B	0.1309	−0.1196	0.3484	0.066*
H7C	0.1754	−0.2159	0.4328	0.066*
C8	0.3314 (4)	0.2851 (6)	0.6694 (5)	0.0269 (16)
H8	0.2915	0.3119	0.6658	0.032*
C9	0.4604 (4)	0.5100 (6)	0.8344 (4)	0.0269 (15)
C10	0.4616 (2)	0.6071 (4)	0.8911 (2)	0.0236 (15)
C11	0.5075 (2)	0.7141 (4)	0.9198 (3)	0.0289 (16)
H11	0.5330	0.7276	0.8990	0.035*
C12	0.5159 (2)	0.8012 (3)	0.9790 (3)	0.0314 (17)
H12	0.5472	0.8743	0.9986	0.038*
C13	0.4785 (2)	0.7813 (4)	1.0094 (3)	0.0282 (16)
C14	0.4326 (2)	0.6744 (4)	0.9807 (3)	0.0241 (14)
H14	0.4071	0.6609	1.0015	0.029*
C15	0.4242 (2)	0.5873 (3)	0.9215 (3)	0.0244 (15)
H15	0.3929	0.5142	0.9019	0.029*
C16	0.1442 (4)	0.4487 (8)	0.7214 (5)	0.0372 (18)
H16A	0.1335	0.3567	0.7154	0.056*
H16B	0.0974	0.4970	0.6902	0.056*
H16C	0.1805	0.4720	0.7858	0.056*
C17	0.1980 (4)	0.6515 (7)	0.6951 (5)	0.0424 (19)
H17A	0.2175	0.6882	0.6690	0.064*
H17B	0.2346	0.6653	0.7609	0.064*
H17C	0.1502	0.6932	0.6682	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0238 (4)	0.0338 (4)	0.0243 (4)	0.000	0.0186 (3)	0.000
S1	0.0368 (10)	0.0355 (11)	0.0337 (11)	−0.0019 (8)	0.0259 (9)	−0.0040 (9)
O1	0.025 (2)	0.037 (3)	0.027 (3)	0.000 (2)	0.019 (2)	0.000 (2)
O2	0.041 (3)	0.041 (3)	0.032 (3)	−0.010 (2)	0.026 (3)	−0.012 (2)
O3	0.025 (2)	0.035 (3)	0.029 (3)	−0.001 (2)	0.022 (2)	−0.003 (2)
O4	0.034 (3)	0.038 (3)	0.032 (3)	−0.007 (2)	0.028 (2)	−0.010 (2)
N1	0.024 (3)	0.026 (3)	0.020 (3)	−0.001 (2)	0.016 (2)	0.000 (2)
N2	0.030 (3)	0.033 (3)	0.025 (3)	0.000 (3)	0.022 (3)	−0.005 (3)
O5	0.035 (3)	0.042 (3)	0.061 (4)	0.004 (2)	0.036 (3)	0.002 (3)
C1	0.025 (3)	0.031 (4)	0.020 (4)	0.006 (3)	0.014 (3)	0.007 (3)
C2	0.034 (4)	0.033 (4)	0.027 (4)	0.007 (3)	0.024 (3)	0.002 (3)
C3	0.037 (4)	0.025 (4)	0.032 (4)	−0.003 (3)	0.025 (4)	0.000 (3)
C4	0.024 (3)	0.045 (5)	0.021 (4)	−0.012 (3)	0.010 (3)	−0.006 (3)
C5	0.030 (4)	0.044 (5)	0.026 (4)	0.005 (3)	0.019 (3)	0.003 (3)
C6	0.027 (3)	0.035 (4)	0.026 (4)	0.007 (3)	0.018 (3)	0.010 (4)
C7	0.047 (4)	0.044 (5)	0.035 (4)	−0.004 (4)	0.025 (4)	−0.002 (4)
C8	0.027 (4)	0.024 (4)	0.035 (4)	0.003 (3)	0.024 (3)	0.005 (3)
C9	0.027 (4)	0.027 (4)	0.022 (4)	0.007 (3)	0.015 (3)	0.006 (3)
C10	0.021 (3)	0.029 (4)	0.020 (4)	−0.002 (3)	0.014 (3)	0.000 (3)
C11	0.035 (4)	0.034 (4)	0.029 (4)	−0.001 (3)	0.026 (3)	−0.002 (3)
C12	0.033 (4)	0.036 (5)	0.035 (4)	−0.006 (3)	0.027 (3)	0.001 (3)
C13	0.035 (4)	0.033 (4)	0.022 (4)	0.005 (3)	0.021 (3)	0.002 (3)
C14	0.025 (3)	0.029 (4)	0.021 (3)	0.004 (3)	0.017 (3)	0.003 (3)
C15	0.026 (3)	0.026 (4)	0.020 (4)	−0.002 (3)	0.015 (3)	0.001 (3)
C16	0.031 (4)	0.051 (5)	0.037 (5)	−0.004 (3)	0.025 (4)	−0.006 (4)
C17	0.050 (4)	0.039 (5)	0.047 (5)	0.004 (4)	0.035 (4)	−0.001 (4)

Geometric parameters (Å, º) top

Cd1—O1	2.246 (4)	C4—H4A	0.9500
Cd1—O1ⁱ	2.246 (4)	C5—C6	1.3900
Cd1—N1ⁱ	2.254 (5)	C5—H5	0.9500
Cd1—N1	2.254 (5)	C6—C8	1.464 (7)
Cd1—O3	2.386 (4)	C7—H7A	0.9800
Cd1—O3ⁱ	2.386 (4)	C7—H7B	0.9800
S1—O5	1.497 (5)	C7—H7C	0.9800
S1—C17	1.764 (7)	C8—H8	0.9500
S1—C16	1.782 (6)	C9—C10	1.500 (7)
O1—C1	1.362 (5)	C10—C11	1.3900
O2—C3	1.355 (5)	C10—C15	1.3900
O2—C7	1.439 (8)	C11—C12	1.3900
O3—C9	1.221 (7)	C11—H11	0.9500
O4—C13	1.356 (5)	C12—C13	1.3900
O4—H4	0.8400	C12—H12	0.9500
N1—C8	1.280 (8)	C13—C14	1.3900
N1—N2	1.385 (7)	C14—C15	1.3900
N2—C9	1.356 (8)	C14—H14	0.9500
N2—H2	0.8800	C15—H15	0.9500
C1—C2	1.3900	C16—H16A	0.9800
C1—C6	1.3900	C16—H16B	0.9800
C2—C3	1.3900	C16—H16C	0.9800
C2—H2A	0.9500	C17—H17A	0.9800
C3—C4	1.3900	C17—H17B	0.9800
C4—C5	1.3900	C17—H17C	0.9800

O1—Cd1—O1ⁱ	101.8 (2)	C5—C6—C8	112.7 (3)
O1—Cd1—N1ⁱ	104.12 (16)	C1—C6—C8	127.3 (3)
O1ⁱ—Cd1—N1ⁱ	82.26 (16)	O2—C7—H7A	109.5
O1—Cd1—N1	82.26 (16)	O2—C7—H7B	109.5
O1ⁱ—Cd1—N1	104.12 (16)	H7A—C7—H7B	109.5
N1ⁱ—Cd1—N1	170.1 (3)	O2—C7—H7C	109.5
O1—Cd1—O3	150.75 (14)	H7A—C7—H7C	109.5
O1ⁱ—Cd1—O3	94.45 (15)	H7B—C7—H7C	109.5
N1ⁱ—Cd1—O3	102.05 (16)	N1—C8—C6	127.4 (5)
N1—Cd1—O3	70.17 (16)	N1—C8—H8	116.3
O1—Cd1—O3ⁱ	94.45 (15)	C6—C8—H8	116.3
O1ⁱ—Cd1—O3ⁱ	150.75 (14)	O3—C9—N2	122.3 (6)
N1ⁱ—Cd1—O3ⁱ	70.17 (16)	O3—C9—C10	121.5 (6)
N1—Cd1—O3ⁱ	102.05 (16)	N2—C9—C10	116.1 (5)
O3—Cd1—O3ⁱ	82.3 (2)	C11—C10—C15	120.0
O5—S1—C17	104.7 (3)	C11—C10—C9	117.7 (3)
O5—S1—C16	104.9 (3)	C15—C10—C9	122.0 (4)
C17—S1—C16	99.3 (4)	C12—C11—C10	120.0
C1—O1—Cd1	130.6 (3)	C12—C11—H11	120.0
C3—O2—C7	117.6 (5)	C10—C11—H11	120.0
C9—O3—Cd1	114.2 (4)	C11—C12—C13	120.0
C13—O4—H4	109.5	C11—C12—H12	120.0
C8—N1—N2	116.5 (5)	C13—C12—H12	120.0
C8—N1—Cd1	128.4 (4)	O4—C13—C14	122.6 (3)
N2—N1—Cd1	114.9 (3)	O4—C13—C12	117.3 (3)
C9—N2—N1	118.2 (5)	C14—C13—C12	120.0
C9—N2—H2	120.9	C13—C14—C15	120.0
N1—N2—H2	120.9	C13—C14—H14	120.0
O1—C1—C2	117.6 (3)	C15—C14—H14	120.0
O1—C1—C6	122.4 (3)	C14—C15—C10	120.0
C2—C1—C6	120.0	C14—C15—H15	120.0
C1—C2—C3	120.0	C10—C15—H15	120.0
C1—C2—H2A	120.0	S1—C16—H16A	109.5
C3—C2—H2A	120.0	S1—C16—H16B	109.5
O2—C3—C2	116.1 (3)	H16A—C16—H16B	109.5
O2—C3—C4	123.9 (3)	S1—C16—H16C	109.5
C2—C3—C4	120.0	H16A—C16—H16C	109.5
C5—C4—C3	120.0	H16B—C16—H16C	109.5
C5—C4—H4A	120.0	S1—C17—H17A	109.5
C3—C4—H4A	120.0	S1—C17—H17B	109.5
C4—C5—C6	120.0	H17A—C17—H17B	109.5
C4—C5—H5	120.0	S1—C17—H17C	109.5
C6—C5—H5	120.0	H17A—C17—H17C	109.5
C5—C6—C1	120.0	H17B—C17—H17C	109.5

O1ⁱ—Cd1—O1—C1	90.7 (4)	C3—C4—C5—C6	0.0
N1ⁱ—Cd1—O1—C1	175.5 (4)	C4—C5—C6—C1	0.0
N1—Cd1—O1—C1	−12.2 (4)	C4—C5—C6—C8	180.0 (4)
O3—Cd1—O1—C1	−31.7 (6)	O1—C1—C6—C5	178.1 (4)
O3ⁱ—Cd1—O1—C1	−113.8 (4)	C2—C1—C6—C5	0.0
O1—Cd1—O3—C9	24.1 (6)	O1—C1—C6—C8	−1.8 (6)
O1ⁱ—Cd1—O3—C9	−99.9 (4)	C2—C1—C6—C8	−179.9 (5)
N1ⁱ—Cd1—O3—C9	177.1 (4)	N2—N1—C8—C6	−178.8 (5)
N1—Cd1—O3—C9	3.5 (4)	Cd1—N1—C8—C6	6.1 (9)
O3ⁱ—Cd1—O3—C9	109.4 (5)	C5—C6—C8—N1	171.3 (6)
O1—Cd1—N1—C8	2.3 (5)	C1—C6—C8—N1	−8.8 (9)
O1ⁱ—Cd1—N1—C8	−97.9 (5)	Cd1—O3—C9—N2	−3.9 (8)
O3—Cd1—N1—C8	172.4 (6)	Cd1—O3—C9—C10	175.5 (4)
O3ⁱ—Cd1—N1—C8	95.3 (5)	N1—N2—C9—O3	1.4 (9)
O1—Cd1—N1—N2	−172.8 (4)	N1—N2—C9—C10	−178.1 (5)
O1ⁱ—Cd1—N1—N2	86.9 (4)	O3—C9—C10—C11	25.7 (7)
O3—Cd1—N1—N2	−2.8 (4)	N2—C9—C10—C11	−154.8 (4)
O3ⁱ—Cd1—N1—N2	−79.9 (4)	O3—C9—C10—C15	−148.5 (5)
C8—N1—N2—C9	−173.7 (6)	N2—C9—C10—C15	31.0 (7)
Cd1—N1—N2—C9	2.1 (7)	C15—C10—C11—C12	0.0
Cd1—O1—C1—C2	−168.0 (3)	C9—C10—C11—C12	−174.3 (4)
Cd1—O1—C1—C6	13.8 (6)	C10—C11—C12—C13	0.0
O1—C1—C2—C3	−178.2 (4)	C11—C12—C13—O4	177.6 (4)
C6—C1—C2—C3	0.0	C11—C12—C13—C14	0.0
C7—O2—C3—C2	174.7 (5)	O4—C13—C14—C15	−177.4 (4)
C7—O2—C3—C4	−6.5 (7)	C12—C13—C14—C15	0.0
C1—C2—C3—O2	178.9 (5)	C13—C14—C15—C10	0.0
C1—C2—C3—C4	0.0	C11—C10—C15—C14	0.0
O2—C3—C4—C5	−178.8 (5)	C9—C10—C15—C14	174.1 (4)
C2—C3—C4—C5	0.0

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O1ⁱⁱ	0.84	1.79	2.603 (6)	163
N2—H2···O5	0.88	1.93	2.766 (6)	159

Symmetry code: (ii) x, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	[Cd(C₁₅H₁₃N₂O₄)₂]·2C₂H₆OS
M_r	839.20
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	118
a, b, c (Å)	23.891 (2), 10.439 (1), 19.874 (1)
β (°)	132.137 (4)
V (Å³)	3675.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.77
Crystal size (mm)	0.12 × 0.06 × 0.03

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.507, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	10208, 3243, 2147
R_int	0.103
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.153, 1.02
No. of reflections	3243
No. of parameters	211
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.31, −0.90

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
O4—H4···O1ⁱ	0.84	1.79	2.603 (6)	163
N2—H2···O5	0.88	1.93	2.766 (6)	159

Symmetry code: (i) x, −y+1, z+1/2.

Acknowledgements

We thank the University of Malaya for supporting this study.

References

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
Mohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, o189. 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. (2009). publCIF. In preparation. Google Scholar

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