[N′-(5-Chloro-2-oxidobenzyl­idene-κO)-3-hydr­oxy-2-naphthohydrazidato-κ2N′,O]dimethyl­tin(IV)

Lee, S.M.; Lo, K.M.; Ali, H.; Ng, S.W.

doi:10.1107/S1600536809022259

metal-organic compounds

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Volume 65| Part 7| July 2009| Page m816

doi:10.1107/S1600536809022259

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[N′-(5-Chloro-2-oxidobenzylidene-κO)-3-hydroxy-2-naphthohydrazidato-κ²N′,O]dimethyltin(IV)

See Mun Lee,^a Kong Mun Lo,^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 10 June 2009; accepted 11 June 2009; online 24 June 2009)

The Sn^IV atom in the title compound, [Sn(CH₃)₂(C₁₈H₁₁ClN₂O₃)], shows a trans-C₂NO₂Sn trigonal-bipyramidal coordination; the axial O—Sn—O angle is 155.22 (5)°. The tridentate N′-(5-chloro-2-oxidobenzylidene)-3-hydroxy-2-naphthohydrazidate dianion is stabilized by an intramolecular O—H⋯N hydrogen bond.

Related literature

The dianions of similar N′-(2-hydroxybenzylidene)benzohydrazones O,N,O′-chelate tin in organotin compounds; see: Labib et al. (1996 ); Samanta et al. (2007 ).

Experimental

Crystal data

[Sn(CH₃)₂(C₁₈H₁₁ClN₂O₃)]
M_r = 487.50
Triclinic, $[P \overline 1]$
a = 6.8374 (1) Å
b = 11.6207 (2) Å
c = 12.0159 (2) Å
α = 86.874 (1)°
β = 75.926 (1)°
γ = 80.635 (1)°
V = 913.61 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.57 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.623, T_max = 0.746 (expected range = 0.714–0.855)
8585 measured reflections
4182 independent reflections
3924 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.019
wR(F²) = 0.049
S = 1.04
4182 reflections
250 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N2	0.83 (1)	1.86 (2)	2.604 (2)	148 (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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022259/tk2476sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022259/tk2476Isup2.hkl

checkCIF report

Related literature top

The dianions of similar N'-(2-hydroxybenzylidene)benzohydrazones O,N,O'-chelate tin in organotin compounds; see: Labib et al. (1996); Samanta et al. (2007).

Experimental top

The Schiff base was synthesized by the condensation of 3-hydroxy-2-naphthoylhydrazide and 5-chorosalicylaldehyde. The Schiff base (0.50 g, 1.5 mmol) and dimethyltin oxide (0.24 g, 1.5 mmol) were heated in methanol until the oxide dissolved completely; the filtered solution yielded yellow crystals when the solvent was allowed to evaporate over a few days.

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, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of (CH₃)₂Sn(C₁₈H₁₁N₂O₃) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

[N'-(5-Chloro-2-oxidobenzylidene-κO)-3-hydroxy- 2-naphthohydrazidato-κ²N',O]dimethyltin(IV) top

Crystal data top

[Sn(CH₃)₂(C₁₈H₁₁ClN₂O₃)]	Z = 2
M_r = 487.50	F(000) = 484
Triclinic, P1	D_x = 1.772 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8374 (1) Å	Cell parameters from 6181 reflections
b = 11.6207 (2) Å	θ = 2.5–28.3°
c = 12.0159 (2) Å	µ = 1.57 mm⁻¹
α = 86.874 (1)°	T = 100 K
β = 75.926 (1)°	Block, yellow
γ = 80.635 (1)°	0.30 × 0.20 × 0.10 mm
V = 913.61 (3) Å³

Data collection top

Bruker SMART APEX diffractometer	4182 independent reflections
Radiation source: fine-focus sealed tube	3924 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.623, T_max = 0.746	k = −14→15
8585 measured reflections	l = −15→15

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)] = 0.019	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0261P)² + 0.3698P] where P = (F_o² + 2F_c²)/3
4182 reflections	(Δ/σ)_max = 0.001
250 parameters	Δρ_max = 0.65 e Å⁻³
1 restraint	Δρ_min = −0.58 e Å⁻³

Crystal data top

[Sn(CH₃)₂(C₁₈H₁₁ClN₂O₃)]	γ = 80.635 (1)°
M_r = 487.50	V = 913.61 (3) Å³
Triclinic, P1	Z = 2
a = 6.8374 (1) Å	Mo Kα radiation
b = 11.6207 (2) Å	µ = 1.57 mm⁻¹
c = 12.0159 (2) Å	T = 100 K
α = 86.874 (1)°	0.30 × 0.20 × 0.10 mm
β = 75.926 (1)°

Data collection top

Bruker SMART APEX diffractometer	4182 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3924 reflections with I > 2σ(I)
T_min = 0.623, T_max = 0.746	R_int = 0.015
8585 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	1 restraint
wR(F²) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.65 e Å⁻³
4182 reflections	Δρ_min = −0.58 e Å⁻³
250 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.249480 (17)	0.940034 (10)	0.829046 (10)	0.01557 (5)
Cl1	0.43674 (7)	1.55715 (4)	0.85417 (4)	0.02564 (11)
O1	0.1479 (2)	1.10418 (11)	0.90330 (12)	0.0216 (3)
O2	0.4251 (2)	0.81921 (11)	0.69992 (12)	0.0232 (3)
O3	0.8870 (2)	0.93252 (12)	0.43301 (12)	0.0248 (3)
H3	0.813 (3)	0.968 (2)	0.4896 (15)	0.033 (7)*
N1	0.4700 (2)	1.03357 (13)	0.71084 (13)	0.0155 (3)
N2	0.6016 (2)	0.96863 (13)	0.62100 (13)	0.0164 (3)
C1	−0.0334 (3)	0.92182 (17)	0.79696 (17)	0.0219 (4)
H1A	−0.1400	0.9331	0.8683	0.033*
H1B	−0.0255	0.8436	0.7680	0.033*
H1C	−0.0663	0.9803	0.7397	0.033*
C2	0.3785 (3)	0.85984 (17)	0.96219 (17)	0.0235 (4)
H2A	0.2742	0.8657	1.0347	0.035*
H2B	0.4913	0.8991	0.9691	0.035*
H2C	0.4299	0.7775	0.9445	0.035*
C3	0.2252 (3)	1.20273 (15)	0.89032 (16)	0.0168 (3)
C4	0.1378 (3)	1.29089 (16)	0.97140 (16)	0.0196 (4)
H4	0.0274	1.2775	1.0335	0.023*
C5	0.2091 (3)	1.39631 (16)	0.96262 (16)	0.0195 (4)
H5	0.1520	1.4533	1.0201	0.023*
C6	0.3645 (3)	1.41882 (15)	0.86956 (16)	0.0188 (4)
C7	0.4554 (3)	1.33520 (16)	0.78900 (16)	0.0179 (4)
H7	0.5623	1.3514	0.7260	0.021*
C8	0.3901 (3)	1.22474 (15)	0.79955 (15)	0.0158 (3)
C9	0.4990 (3)	1.14094 (15)	0.71396 (15)	0.0160 (3)
H9	0.6020	1.1665	0.6539	0.019*
C10	0.5659 (3)	0.86010 (15)	0.62363 (15)	0.0162 (3)
C11	0.6967 (3)	0.78165 (15)	0.53296 (15)	0.0154 (3)
C12	0.8488 (3)	0.82057 (15)	0.44149 (16)	0.0173 (3)
C13	0.9604 (3)	0.74493 (16)	0.35706 (15)	0.0178 (4)
H13	1.0587	0.7723	0.2955	0.021*
C14	0.9313 (3)	0.62645 (16)	0.36032 (15)	0.0164 (3)
C15	1.0449 (3)	0.54640 (16)	0.27417 (15)	0.0188 (4)
H15	1.1414	0.5723	0.2107	0.023*
C16	1.0161 (3)	0.43211 (17)	0.28209 (16)	0.0206 (4)
H16	1.0941	0.3794	0.2243	0.025*
C17	0.8725 (3)	0.39148 (16)	0.37463 (17)	0.0208 (4)
H17	0.8534	0.3120	0.3787	0.025*
C18	0.7606 (3)	0.46675 (16)	0.45860 (16)	0.0181 (4)
H18	0.6647	0.4390	0.5212	0.022*
C19	0.7861 (3)	0.58623 (15)	0.45330 (15)	0.0161 (3)
C20	0.6700 (3)	0.66597 (15)	0.53765 (15)	0.0159 (3)
H20	0.5708	0.6395	0.5993	0.019*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01565 (7)	0.01387 (7)	0.01579 (7)	−0.00315 (4)	−0.00023 (5)	−0.00126 (4)
Cl1	0.0265 (2)	0.0153 (2)	0.0333 (3)	−0.00562 (17)	−0.0009 (2)	−0.00611 (18)
O1	0.0212 (7)	0.0156 (6)	0.0240 (7)	−0.0042 (5)	0.0037 (5)	−0.0026 (5)
O2	0.0250 (7)	0.0166 (7)	0.0237 (7)	−0.0071 (5)	0.0057 (6)	−0.0045 (5)
O3	0.0301 (8)	0.0177 (7)	0.0224 (7)	−0.0094 (6)	0.0066 (6)	−0.0051 (5)
N1	0.0150 (7)	0.0161 (7)	0.0144 (7)	−0.0019 (6)	−0.0017 (6)	−0.0022 (6)
N2	0.0166 (7)	0.0159 (7)	0.0150 (7)	−0.0024 (6)	0.0001 (6)	−0.0035 (6)
C1	0.0196 (9)	0.0252 (10)	0.0209 (9)	−0.0074 (7)	−0.0026 (7)	0.0010 (7)
C2	0.0263 (10)	0.0207 (9)	0.0238 (10)	−0.0013 (8)	−0.0079 (8)	−0.0008 (7)
C3	0.0166 (8)	0.0149 (8)	0.0190 (9)	−0.0012 (6)	−0.0050 (7)	−0.0004 (7)
C4	0.0189 (9)	0.0195 (9)	0.0174 (9)	−0.0003 (7)	−0.0005 (7)	−0.0009 (7)
C5	0.0200 (9)	0.0166 (9)	0.0205 (9)	0.0032 (7)	−0.0052 (7)	−0.0045 (7)
C6	0.0214 (9)	0.0130 (8)	0.0229 (9)	−0.0027 (7)	−0.0067 (7)	−0.0019 (7)
C7	0.0167 (8)	0.0184 (9)	0.0184 (9)	−0.0032 (7)	−0.0033 (7)	−0.0006 (7)
C8	0.0170 (8)	0.0140 (8)	0.0163 (8)	−0.0006 (6)	−0.0048 (7)	−0.0017 (6)
C9	0.0158 (8)	0.0160 (8)	0.0159 (8)	−0.0032 (6)	−0.0027 (7)	0.0003 (6)
C10	0.0161 (8)	0.0169 (9)	0.0155 (8)	−0.0025 (7)	−0.0032 (7)	−0.0008 (7)
C11	0.0143 (8)	0.0162 (8)	0.0157 (8)	−0.0018 (6)	−0.0037 (7)	−0.0021 (6)
C12	0.0192 (9)	0.0155 (8)	0.0177 (9)	−0.0041 (7)	−0.0044 (7)	0.0000 (7)
C13	0.0168 (8)	0.0208 (9)	0.0150 (8)	−0.0048 (7)	−0.0010 (7)	−0.0003 (7)
C14	0.0149 (8)	0.0200 (9)	0.0150 (8)	−0.0015 (7)	−0.0051 (7)	−0.0027 (7)
C15	0.0181 (9)	0.0228 (9)	0.0145 (9)	−0.0018 (7)	−0.0022 (7)	−0.0029 (7)
C16	0.0215 (9)	0.0214 (9)	0.0187 (9)	−0.0002 (7)	−0.0048 (7)	−0.0069 (7)
C17	0.0213 (9)	0.0161 (9)	0.0260 (10)	−0.0026 (7)	−0.0072 (8)	−0.0030 (7)
C18	0.0168 (8)	0.0184 (9)	0.0191 (9)	−0.0028 (7)	−0.0042 (7)	−0.0011 (7)
C19	0.0149 (8)	0.0174 (9)	0.0166 (8)	−0.0017 (7)	−0.0049 (7)	−0.0024 (7)
C20	0.0148 (8)	0.0169 (9)	0.0149 (8)	−0.0028 (6)	−0.0014 (7)	−0.0015 (6)

Geometric parameters (Å, º) top

Sn1—O1	2.091 (1)	C5—H5	0.9500
Sn1—O2	2.146 (1)	C6—C7	1.371 (2)
Sn1—N1	2.190 (2)	C7—C8	1.416 (2)
Sn1—C1	2.107 (2)	C7—H7	0.9500
Sn1—C2	2.113 (2)	C8—C9	1.436 (2)
Cl1—C6	1.745 (2)	C9—H9	0.9500
O1—C3	1.324 (2)	C10—C11	1.479 (2)
O2—C10	1.291 (2)	C11—C20	1.382 (2)
O3—C12	1.362 (2)	C11—C12	1.427 (2)
O3—H3	0.828 (10)	C12—C13	1.374 (2)
N1—C9	1.299 (2)	C13—C14	1.420 (3)
N1—N2	1.393 (2)	C13—H13	0.9500
N2—C10	1.320 (2)	C14—C19	1.417 (3)
C1—H1A	0.9800	C14—C15	1.421 (2)
C1—H1B	0.9800	C15—C16	1.369 (3)
C1—H1C	0.9800	C15—H15	0.9500
C2—H2A	0.9800	C16—C17	1.409 (3)
C2—H2B	0.9800	C16—H16	0.9500
C2—H2C	0.9800	C17—C18	1.368 (3)
C3—C8	1.411 (3)	C17—H17	0.9500
C3—C4	1.408 (2)	C18—C19	1.423 (3)
C4—C5	1.380 (3)	C18—H18	0.9500
C4—H4	0.9500	C19—C20	1.410 (2)
C5—C6	1.389 (3)	C20—H20	0.9500

O1—Sn1—C1	95.03 (7)	C6—C7—H7	120.0
O1—Sn1—C2	97.04 (7)	C8—C7—H7	120.0
C1—Sn1—C2	127.30 (8)	C3—C8—C7	119.79 (16)
O1—Sn1—O2	155.22 (5)	C3—C8—C9	123.84 (16)
C1—Sn1—O2	94.59 (7)	C7—C8—C9	116.37 (16)
C2—Sn1—O2	95.16 (7)	N1—C9—C8	126.20 (16)
O1—Sn1—N1	82.77 (5)	N1—C9—H9	116.9
C1—Sn1—N1	122.40 (7)	C8—C9—H9	116.9
C2—Sn1—N1	109.96 (7)	O2—C10—N2	124.04 (16)
O2—Sn1—N1	72.80 (5)	O2—C10—C11	118.68 (15)
C3—O1—Sn1	133.18 (12)	N2—C10—C11	117.28 (16)
C10—O2—Sn1	115.30 (11)	C20—C11—C12	118.99 (16)
C12—O3—H3	108.0 (18)	C20—C11—C10	118.33 (16)
C9—N1—N2	114.99 (15)	C12—C11—C10	122.69 (16)
C9—N1—Sn1	129.10 (12)	O3—C12—C13	117.62 (16)
N2—N1—Sn1	115.88 (11)	O3—C12—C11	122.19 (16)
C10—N2—N1	111.96 (14)	C13—C12—C11	120.18 (16)
Sn1—C1—H1A	109.5	C12—C13—C14	121.08 (17)
Sn1—C1—H1B	109.5	C12—C13—H13	119.5
H1A—C1—H1B	109.5	C14—C13—H13	119.5
Sn1—C1—H1C	109.5	C19—C14—C15	118.84 (16)
H1A—C1—H1C	109.5	C19—C14—C13	118.96 (16)
H1B—C1—H1C	109.5	C15—C14—C13	122.20 (17)
Sn1—C2—H2A	109.5	C16—C15—C14	120.38 (17)
Sn1—C2—H2B	109.5	C16—C15—H15	119.8
H2A—C2—H2B	109.5	C14—C15—H15	119.8
Sn1—C2—H2C	109.5	C15—C16—C17	121.04 (17)
H2A—C2—H2C	109.5	C15—C16—H16	119.5
H2B—C2—H2C	109.5	C17—C16—H16	119.5
O1—C3—C8	123.74 (16)	C18—C17—C16	119.80 (17)
O1—C3—C4	118.25 (16)	C18—C17—H17	120.1
C8—C3—C4	118.00 (16)	C16—C17—H17	120.1
C5—C4—C3	121.42 (17)	C17—C18—C19	120.79 (17)
C5—C4—H4	119.3	C17—C18—H18	119.6
C3—C4—H4	119.3	C19—C18—H18	119.6
C4—C5—C6	119.82 (17)	C20—C19—C14	119.00 (16)
C4—C5—H5	120.1	C20—C19—C18	121.86 (17)
C6—C5—H5	120.1	C14—C19—C18	119.14 (16)
C7—C6—C5	120.72 (17)	C11—C20—C19	121.72 (17)
C7—C6—Cl1	120.41 (15)	C11—C20—H20	119.1
C5—C6—Cl1	118.83 (14)	C19—C20—H20	119.1
C6—C7—C8	120.09 (17)

C1—Sn1—O1—C3	−134.26 (17)	Sn1—N1—C9—C8	0.8 (3)
C2—Sn1—O1—C3	97.15 (17)	C3—C8—C9—N1	−3.8 (3)
O2—Sn1—O1—C3	−21.8 (2)	C7—C8—C9—N1	176.64 (17)
N1—Sn1—O1—C3	−12.18 (16)	Sn1—O2—C10—N2	−1.3 (2)
O1—Sn1—O2—C10	11.1 (2)	Sn1—O2—C10—C11	178.74 (12)
C1—Sn1—O2—C10	123.65 (14)	N1—N2—C10—O2	0.4 (2)
C2—Sn1—O2—C10	−108.21 (14)	N1—N2—C10—C11	−179.60 (14)
N1—Sn1—O2—C10	1.11 (12)	O2—C10—C11—C20	−3.6 (2)
O1—Sn1—N1—C9	5.00 (15)	N2—C10—C11—C20	176.39 (16)
C1—Sn1—N1—C9	96.39 (16)	O2—C10—C11—C12	176.49 (17)
C2—Sn1—N1—C9	−89.90 (16)	N2—C10—C11—C12	−3.5 (3)
O2—Sn1—N1—C9	−179.19 (17)	C20—C11—C12—O3	−178.33 (17)
O1—Sn1—N1—N2	−176.74 (12)	C10—C11—C12—O3	1.6 (3)
C1—Sn1—N1—N2	−85.36 (13)	C20—C11—C12—C13	2.7 (3)
C2—Sn1—N1—N2	88.36 (12)	C10—C11—C12—C13	−177.41 (16)
O2—Sn1—N1—N2	−0.93 (11)	O3—C12—C13—C14	179.31 (16)
C9—N1—N2—C10	179.15 (15)	C11—C12—C13—C14	−1.7 (3)
Sn1—N1—N2—C10	0.64 (18)	C12—C13—C14—C19	−0.8 (3)
Sn1—O1—C3—C8	13.4 (3)	C12—C13—C14—C15	−179.92 (17)
Sn1—O1—C3—C4	−166.82 (13)	C19—C14—C15—C16	−0.9 (3)
O1—C3—C4—C5	−179.32 (17)	C13—C14—C15—C16	178.26 (17)
C8—C3—C4—C5	0.5 (3)	C14—C15—C16—C17	0.7 (3)
C3—C4—C5—C6	2.8 (3)	C15—C16—C17—C18	−0.5 (3)
C4—C5—C6—C7	−3.3 (3)	C16—C17—C18—C19	0.5 (3)
C4—C5—C6—Cl1	174.59 (14)	C15—C14—C19—C20	−178.65 (16)
C5—C6—C7—C8	0.5 (3)	C13—C14—C19—C20	2.2 (2)
Cl1—C6—C7—C8	−177.37 (14)	C15—C14—C19—C18	0.9 (2)
O1—C3—C8—C7	176.52 (17)	C13—C14—C19—C18	−178.24 (16)
C4—C3—C8—C7	−3.3 (3)	C17—C18—C19—C20	178.81 (17)
O1—C3—C8—C9	−3.0 (3)	C17—C18—C19—C14	−0.8 (3)
C4—C3—C8—C9	177.20 (16)	C12—C11—C20—C19	−1.3 (3)
C6—C7—C8—C3	2.9 (3)	C10—C11—C20—C19	178.82 (15)
C6—C7—C8—C9	−177.61 (16)	C14—C19—C20—C11	−1.1 (3)
N2—N1—C9—C8	−177.52 (16)	C18—C19—C20—C11	179.27 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.83 (1)	1.86 (2)	2.604 (2)	148 (2)

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)₂(C₁₈H₁₁ClN₂O₃)]
M_r	487.50
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.8374 (1), 11.6207 (2), 12.0159 (2)
α, β, γ (°)	86.874 (1), 75.926 (1), 80.635 (1)
V (Å³)	913.61 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.57
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.623, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	8585, 4182, 3924
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.019, 0.049, 1.04
No. of reflections	4182
No. of parameters	250
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.58

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), 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
O3—H3···N2	0.83 (1)	1.86 (2)	2.604 (2)	148 (2)

Acknowledgements

We thank the University of Malaya (PS320/2008C, RG020/09AFR) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
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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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