(Acetyl­acetone 3-hy­droxy-2-naphtho­yl­hydrazonato-κ3O,N′,O′)(methoxo-κO)oxidovanadate(V)

Wong, H.W.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536810028898

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m1021

https://doi.org/10.1107/S1600536810028898

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(Acetylacetone 3-hydroxy-2-naphthoylhydrazonato-κ³O,N′,O′)(methoxo-κO)oxidovanadate(V)

Hon Wee Wong,^a Kong Mun Lo ^a and Seik Weng Ng ^a ^*

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

(Received 15 July 2010; accepted 20 July 2010; online 24 July 2010)

The tridentate Schiff base ligand in the title compound, [V(C₁₆H₁₄N₂O₃)(CH₃O)O], has its O, N and O′ atoms spanning three basal positions of the square-based-pyrimidally V^V atom. The fourth basal site is occupied by a methoxo ligand, which results from a deprotonated methanol solvent molecule, and the oxido ligand occupies the apical position. The hydroxy H atom forms an intramolecular O—H⋯N hydrogen bond with an N-atom acceptor site.

Related literature

For related vanadium(V) structures, see: Shao et al. (1988 ). The reaction of oxovanadium(IV) bis(acetylacetonate), VO(acac)₂, with aroylhydrazines in methanol yields Schiff-base complexes having the dinuclear [V(=O)(μ-OMe)₂V(=O)]⁴⁺ core, see: Sarkari & Pal (2009 ).

Experimental

Crystal data

[V(C₁₆H₁₄N₂O₃)(CH₃O)O]
M_r = 380.27
Triclinic, $[P \overline 1]$
a = 7.7379 (8) Å
b = 9.7753 (10) Å
c = 11.4411 (11) Å
α = 86.618 (1)°
β = 70.821 (1)°
γ = 85.974 (1)°
V = 814.77 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.64 mm⁻¹
T = 100 K
0.30 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.831, T_max = 0.939
7840 measured reflections
3716 independent reflections
3013 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.102
S = 1.03
3716 reflections
233 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.42 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)	1.91 (2)	2.623 (2)	144 (3)

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); 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, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810028898/nk2050sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810028898/nk2050Isup2.hkl

checkCIF report

Comment top

The reaction of oxovanadium(IV) bis(acetylacetonate), VO(acac)₂, with aroylhydrazines in acetonitrile yields vanadium(V) compounds of the formulation V₂O₃L₂ (where L represents the doubly-deprotonated Schiff base). In methanol, the reaction yields Schiff-base complexes having the dinuclear [V(=O)(µ-OMe)₂V(=O)]⁴⁺ core (Sarkari & Pal, 2009). In the present study, the reaction with a hydroxy-substituted naphthanoic acid hydrazide yields the expected vanadium(V) complex of the doubly-deprotonated Schiff base but a molecule of the solvent is reduced to a methoxide ion (Scheme I). The metal center has square-based pyramidal coordination geometry, with the O,N,O'-atoms of the Schiff base spanning the basal sites, the fourth basal site is occupied by a methoxy ligand and the apical site is occupied by an oxo ligand.

Related literature top

For related vanadium(V) structures, see: Shao et al. (1988). The reaction of oxovanadium(IV) bis(acetylacetonate), VO(acac)₂, with aroylhydrazines in methanol yields Schiff-base complexes having the dinuclear [V(=O)(µ-OMe)₂V(=O)]⁴⁺ core, see: Sarkari & Pal (2009).

Experimental top

Bis(acetylacetonato)oxovanadium(IV) (0.20 g, 0.75 mmol) and 3-hydroxy-2-naphthoyl hydrazide (0.15 g, 0.75 mmol) were heated in methanol (100 ml) for one hour. The brown solution was filtered; slow evaporation of the filtrate afforded brown crystals.

Structure description top

For related vanadium(V) structures, see: Shao et al. (1988). The reaction of oxovanadium(IV) bis(acetylacetonate), VO(acac)₂, with aroylhydrazines in methanol yields Schiff-base complexes having the dinuclear [V(=O)(µ-OMe)₂V(=O)]⁴⁺ core, see: Sarkari & Pal (2009).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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, 2010).

Figures top

Fig. 1. Displacement ellipsoid plot of VO(CH₃O)(C₁₆H₁₄N₂O₃) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

(Acetylacetone 3-hydroxy-2-naphthoylhydrazonato-κ³O,N',O')(methoxo- κO)oxidovanadate(V) top

Crystal data top

[V(C₁₆H₁₄N₂O₃)(CH₃O)O]	Z = 2
M_r = 380.27	F(000) = 392
Triclinic, P1	D_x = 1.550 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7379 (8) Å	Cell parameters from 2783 reflections
b = 9.7753 (10) Å	θ = 2.8–28.1°
c = 11.4411 (11) Å	µ = 0.64 mm⁻¹
α = 86.618 (1)°	T = 100 K
β = 70.821 (1)°	Prism, brown
γ = 85.974 (1)°	0.30 × 0.10 × 0.10 mm
V = 814.77 (14) Å³

Data collection top

Bruker SMART APEX diffractometer	3716 independent reflections
Radiation source: fine-focus sealed tube	3013 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
T_min = 0.831, T_max = 0.939	k = −12→12
7840 measured reflections	l = −14→14

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0499P)² + 0.2795P] where P = (F_o² + 2F_c²)/3
3716 reflections	(Δ/σ)_max = 0.001
233 parameters	Δρ_max = 0.75 e Å⁻³
1 restraint	Δρ_min = −0.42 e Å⁻³

Crystal data top

[V(C₁₆H₁₄N₂O₃)(CH₃O)O]	γ = 85.974 (1)°
M_r = 380.27	V = 814.77 (14) Å³
Triclinic, P1	Z = 2
a = 7.7379 (8) Å	Mo Kα radiation
b = 9.7753 (10) Å	µ = 0.64 mm⁻¹
c = 11.4411 (11) Å	T = 100 K
α = 86.618 (1)°	0.30 × 0.10 × 0.10 mm
β = 70.821 (1)°

Data collection top

Bruker SMART APEX diffractometer	3716 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3013 reflections with I > 2σ(I)
T_min = 0.831, T_max = 0.939	R_int = 0.027
7840 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	1 restraint
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.75 e Å⁻³
3716 reflections	Δρ_min = −0.42 e Å⁻³
233 parameters

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

	x	y	z	U_iso*/U_eq
V1	1.03271 (5)	0.59868 (4)	0.20412 (3)	0.01980 (12)
O1	1.23385 (19)	0.48290 (15)	0.12970 (13)	0.0226 (3)
O2	0.90127 (19)	0.68028 (15)	0.35967 (13)	0.0215 (3)
O3	0.5685 (2)	0.44133 (16)	0.65797 (15)	0.0270 (4)
H3	0.642 (3)	0.413 (3)	0.5925 (17)	0.052 (9)*
O4	0.8957 (2)	0.58562 (17)	0.12891 (14)	0.0268 (4)
O5	1.1345 (2)	0.75747 (15)	0.15366 (13)	0.0242 (3)
N1	0.9533 (2)	0.43490 (19)	0.32837 (15)	0.0200 (4)
N2	0.8269 (2)	0.46643 (18)	0.44290 (15)	0.0197 (4)
C1	1.4016 (3)	0.3021 (2)	0.0049 (2)	0.0262 (5)
H1A	1.5157	0.3390	0.0056	0.039*
H1B	1.3764	0.3345	−0.0709	0.039*
H1C	1.4138	0.2016	0.0077	0.039*
C2	1.2480 (3)	0.3493 (2)	0.11473 (19)	0.0226 (5)
C3	1.1325 (3)	0.2624 (2)	0.1970 (2)	0.0237 (5)
H3a	1.1440	0.1681	0.1786	0.028*
C4	0.9969 (3)	0.3040 (2)	0.30769 (19)	0.0211 (4)
C5	0.9049 (3)	0.1972 (2)	0.4039 (2)	0.0246 (5)
H5A	0.7716	0.2123	0.4263	0.037*
H5B	0.9413	0.2040	0.4776	0.037*
H5C	0.9418	0.1057	0.3704	0.037*
C6	0.8042 (3)	0.5988 (2)	0.45013 (18)	0.0197 (4)
C7	0.6691 (3)	0.6619 (2)	0.55786 (18)	0.0191 (4)
C8	0.5524 (3)	0.5805 (2)	0.65770 (19)	0.0202 (4)
C9	0.4232 (3)	0.6431 (2)	0.75423 (19)	0.0213 (4)
H9	0.3474	0.5883	0.8199	0.026*
C10	0.3994 (3)	0.7875 (2)	0.75869 (19)	0.0197 (4)
C11	0.2617 (3)	0.8555 (2)	0.8555 (2)	0.0240 (5)
H11	0.1839	0.8029	0.9221	0.029*
C12	0.2394 (3)	0.9953 (2)	0.8542 (2)	0.0262 (5)
H12	0.1459	1.0386	0.9197	0.031*
C13	0.3529 (3)	1.0762 (2)	0.7572 (2)	0.0257 (5)
H13	0.3356	1.1733	0.7572	0.031*
C14	0.4881 (3)	1.0143 (2)	0.6631 (2)	0.0227 (5)
H14	0.5653	1.0692	0.5982	0.027*
C15	0.5148 (3)	0.8695 (2)	0.66085 (18)	0.0187 (4)
C16	0.6479 (3)	0.8029 (2)	0.56254 (18)	0.0194 (4)
H16	0.7259	0.8569	0.4972	0.023*
C17	1.2231 (3)	0.8381 (2)	0.2134 (2)	0.0286 (5)
H17A	1.1333	0.8741	0.2889	0.043*
H17B	1.2789	0.9146	0.1577	0.043*
H17C	1.3185	0.7813	0.2350	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.01469 (19)	0.0299 (2)	0.01415 (19)	−0.00336 (14)	−0.00424 (14)	0.00440 (14)
O1	0.0149 (7)	0.0334 (8)	0.0186 (8)	−0.0038 (6)	−0.0041 (6)	0.0014 (6)
O2	0.0170 (7)	0.0285 (8)	0.0160 (7)	−0.0034 (6)	−0.0019 (6)	0.0047 (6)
O3	0.0288 (9)	0.0262 (8)	0.0201 (8)	−0.0047 (7)	0.0000 (7)	0.0030 (6)
O4	0.0197 (8)	0.0417 (9)	0.0203 (8)	−0.0049 (7)	−0.0089 (6)	0.0057 (7)
O5	0.0217 (8)	0.0306 (8)	0.0167 (8)	−0.0047 (6)	−0.0013 (6)	0.0030 (6)
N1	0.0127 (8)	0.0318 (10)	0.0147 (9)	−0.0022 (7)	−0.0037 (7)	0.0017 (7)
N2	0.0134 (8)	0.0310 (10)	0.0138 (8)	−0.0012 (7)	−0.0036 (7)	0.0019 (7)
C1	0.0187 (11)	0.0391 (13)	0.0203 (11)	−0.0008 (9)	−0.0058 (9)	−0.0006 (9)
C2	0.0183 (11)	0.0336 (12)	0.0185 (11)	−0.0018 (9)	−0.0096 (9)	−0.0002 (9)
C3	0.0213 (11)	0.0293 (11)	0.0218 (11)	−0.0009 (9)	−0.0083 (9)	−0.0029 (9)
C4	0.0165 (10)	0.0297 (11)	0.0200 (11)	−0.0032 (8)	−0.0100 (8)	0.0012 (9)
C5	0.0225 (11)	0.0292 (12)	0.0208 (11)	−0.0035 (9)	−0.0055 (9)	0.0021 (9)
C6	0.0140 (10)	0.0319 (12)	0.0146 (10)	−0.0035 (8)	−0.0072 (8)	0.0048 (8)
C7	0.0140 (10)	0.0296 (11)	0.0140 (10)	−0.0031 (8)	−0.0053 (8)	0.0044 (8)
C8	0.0183 (10)	0.0272 (11)	0.0175 (10)	−0.0042 (8)	−0.0095 (8)	0.0045 (8)
C9	0.0179 (10)	0.0305 (11)	0.0157 (10)	−0.0068 (9)	−0.0059 (8)	0.0066 (8)
C10	0.0157 (10)	0.0312 (11)	0.0148 (10)	−0.0045 (8)	−0.0085 (8)	0.0038 (8)
C11	0.0164 (10)	0.0373 (13)	0.0175 (11)	−0.0034 (9)	−0.0049 (8)	0.0043 (9)
C12	0.0192 (11)	0.0370 (13)	0.0206 (11)	0.0031 (9)	−0.0049 (9)	−0.0019 (9)
C13	0.0259 (12)	0.0280 (11)	0.0250 (12)	−0.0006 (9)	−0.0110 (9)	−0.0002 (9)
C14	0.0211 (11)	0.0293 (11)	0.0190 (11)	−0.0053 (9)	−0.0083 (9)	0.0061 (9)
C15	0.0153 (10)	0.0271 (11)	0.0157 (10)	−0.0022 (8)	−0.0082 (8)	0.0029 (8)
C16	0.0139 (10)	0.0300 (11)	0.0152 (10)	−0.0064 (8)	−0.0065 (8)	0.0073 (8)
C17	0.0321 (13)	0.0277 (12)	0.0227 (12)	−0.0055 (10)	−0.0032 (10)	−0.0023 (9)

Geometric parameters (Å, º) top

V1—O4	1.5850 (15)	C5—H5C	0.9800
V1—O5	1.7693 (15)	C6—C7	1.465 (3)
V1—O1	1.8504 (15)	C7—C16	1.378 (3)
V1—O2	1.9242 (15)	C7—C8	1.439 (3)
V1—N1	2.0632 (17)	C8—C9	1.365 (3)
O1—C2	1.319 (3)	C9—C10	1.412 (3)
O2—C6	1.322 (2)	C9—H9	0.9500
O3—C8	1.357 (3)	C10—C11	1.420 (3)
O3—H3	0.828 (10)	C10—C15	1.425 (3)
O5—C17	1.416 (3)	C11—C12	1.365 (3)
N1—C4	1.315 (3)	C11—H11	0.9500
N1—N2	1.390 (2)	C12—C13	1.408 (3)
N2—C6	1.297 (3)	C12—H12	0.9500
C1—C2	1.488 (3)	C13—C14	1.367 (3)
C1—H1A	0.9800	C13—H13	0.9500
C1—H1B	0.9800	C14—C15	1.417 (3)
C1—H1C	0.9800	C14—H14	0.9500
C2—C3	1.366 (3)	C15—C16	1.408 (3)
C3—C4	1.414 (3)	C16—H16	0.9500
C3—H3a	0.9500	C17—H17A	0.9800
C4—C5	1.504 (3)	C17—H17B	0.9800
C5—H5A	0.9800	C17—H17C	0.9800
C5—H5B	0.9800

O4—V1—O5	105.62 (8)	N2—C6—O2	120.77 (19)
O4—V1—O1	105.47 (8)	N2—C6—C7	121.02 (18)
O5—V1—O1	98.56 (7)	O2—C6—C7	118.20 (18)
O4—V1—O2	108.97 (7)	C16—C7—C8	118.74 (19)
O5—V1—O2	87.78 (6)	C16—C7—C6	119.59 (18)
O1—V1—O2	141.78 (6)	C8—C7—C6	121.63 (19)
O4—V1—N1	98.68 (7)	O3—C8—C9	118.97 (19)
O5—V1—N1	153.82 (7)	O3—C8—C7	121.06 (19)
O1—V1—N1	83.93 (7)	C9—C8—C7	120.0 (2)
O2—V1—N1	75.08 (7)	C8—C9—C10	121.51 (19)
C2—O1—V1	131.01 (13)	C8—C9—H9	119.2
C6—O2—V1	117.27 (13)	C10—C9—H9	119.2
C8—O3—H3	112 (2)	C9—C10—C11	122.76 (19)
C17—O5—V1	128.78 (13)	C9—C10—C15	119.14 (19)
C4—N1—N2	116.69 (17)	C11—C10—C15	118.09 (19)
C4—N1—V1	127.25 (14)	C12—C11—C10	120.9 (2)
N2—N1—V1	115.79 (13)	C12—C11—H11	119.5
C6—N2—N1	108.95 (17)	C10—C11—H11	119.5
C2—C1—H1A	109.5	C11—C12—C13	121.0 (2)
C2—C1—H1B	109.5	C11—C12—H12	119.5
H1A—C1—H1B	109.5	C13—C12—H12	119.5
C2—C1—H1C	109.5	C14—C13—C12	119.7 (2)
H1A—C1—H1C	109.5	C14—C13—H13	120.1
H1B—C1—H1C	109.5	C12—C13—H13	120.1
O1—C2—C3	121.7 (2)	C13—C14—C15	120.9 (2)
O1—C2—C1	114.88 (19)	C13—C14—H14	119.5
C3—C2—C1	123.4 (2)	C15—C14—H14	119.5
C2—C3—C4	124.2 (2)	C16—C15—C14	122.15 (19)
C2—C3—H3a	117.9	C16—C15—C10	118.45 (19)
C4—C3—H3a	117.9	C14—C15—C10	119.37 (19)
N1—C4—C3	120.71 (19)	C7—C16—C15	122.19 (18)
N1—C4—C5	119.81 (19)	C7—C16—H16	118.9
C3—C4—C5	119.47 (19)	C15—C16—H16	118.9
C4—C5—H5A	109.5	O5—C17—H17A	109.5
C4—C5—H5B	109.5	O5—C17—H17B	109.5
H5A—C5—H5B	109.5	H17A—C17—H17B	109.5
C4—C5—H5C	109.5	O5—C17—H17C	109.5
H5A—C5—H5C	109.5	H17A—C17—H17C	109.5
H5B—C5—H5C	109.5	H17B—C17—H17C	109.5

O4—V1—O1—C2	−60.18 (18)	N1—N2—C6—O2	−3.3 (2)
O5—V1—O1—C2	−169.10 (17)	N1—N2—C6—C7	175.95 (16)
O2—V1—O1—C2	93.57 (19)	V1—O2—C6—N2	13.9 (2)
N1—V1—O1—C2	37.18 (17)	V1—O2—C6—C7	−165.34 (13)
O4—V1—O2—C6	81.17 (14)	N2—C6—C7—C16	−179.81 (18)
O5—V1—O2—C6	−173.06 (14)	O2—C6—C7—C16	−0.5 (3)
O1—V1—O2—C6	−72.03 (17)	N2—C6—C7—C8	−2.0 (3)
N1—V1—O2—C6	−13.05 (13)	O2—C6—C7—C8	177.25 (17)
O4—V1—O5—C17	159.55 (17)	C16—C7—C8—O3	−179.55 (18)
O1—V1—O5—C17	−91.66 (18)	C6—C7—C8—O3	2.6 (3)
O2—V1—O5—C17	50.46 (17)	C16—C7—C8—C9	0.4 (3)
N1—V1—O5—C17	2.0 (3)	C6—C7—C8—C9	−177.42 (18)
O4—V1—N1—C4	77.84 (18)	O3—C8—C9—C10	−179.64 (18)
O5—V1—N1—C4	−124.0 (2)	C7—C8—C9—C10	0.4 (3)
O1—V1—N1—C4	−26.94 (17)	C8—C9—C10—C11	177.58 (19)
O2—V1—N1—C4	−174.72 (18)	C8—C9—C10—C15	−0.8 (3)
O4—V1—N1—N2	−95.99 (14)	C9—C10—C11—C12	−177.81 (19)
O5—V1—N1—N2	62.2 (2)	C15—C10—C11—C12	0.6 (3)
O1—V1—N1—N2	159.23 (13)	C10—C11—C12—C13	−0.3 (3)
O2—V1—N1—N2	11.45 (12)	C11—C12—C13—C14	−0.3 (3)
C4—N1—N2—C6	177.68 (17)	C12—C13—C14—C15	0.7 (3)
V1—N1—N2—C6	−7.82 (19)	C13—C14—C15—C16	177.35 (19)
V1—O1—C2—C3	−29.6 (3)	C13—C14—C15—C10	−0.4 (3)
V1—O1—C2—C1	152.33 (15)	C9—C10—C15—C16	0.4 (3)
O1—C2—C3—C4	−4.0 (3)	C11—C10—C15—C16	−178.07 (18)
C1—C2—C3—C4	173.90 (19)	C9—C10—C15—C14	178.22 (18)
N2—N1—C4—C3	−176.11 (17)	C11—C10—C15—C14	−0.3 (3)
V1—N1—C4—C3	10.1 (3)	C8—C7—C16—C15	−0.8 (3)
N2—N1—C4—C5	2.5 (3)	C6—C7—C16—C15	177.05 (18)
V1—N1—C4—C5	−171.27 (14)	C14—C15—C16—C7	−177.34 (19)
C2—C3—C4—N1	11.5 (3)	C10—C15—C16—C7	0.4 (3)
C2—C3—C4—C5	−167.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.83 (1)	1.91 (2)	2.623 (2)	144 (3)

Experimental details

Crystal data
Chemical formula	[V(C₁₆H₁₄N₂O₃)(CH₃O)O]
M_r	380.27
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.7379 (8), 9.7753 (10), 11.4411 (11)
α, β, γ (°)	86.618 (1), 70.821 (1), 85.974 (1)
V (Å³)	814.77 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.64
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.831, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	7840, 3716, 3013
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.102, 1.03
No. of reflections	3716
No. of parameters	233
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)	0.75, −0.42

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SAINT, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.83 (1)	1.91 (2)	2.623 (2)	144 (3)

Acknowledgements

We thank the University of Malaya (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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Shao, M.-C., Zhang, Y.-J., Zhang, Z.-Y. & Tang, Y.-Q. (1988). Sci. Chin. Ser. B (Engl. Ed.), 31, 781–788. 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. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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