(2,2′-Bipyridine-κ2N,N′)(4-hydr­oxy-2-oxidobenzaldehyde thio­semicar­ba­zon­ato-κ3O2,N1,S)zinc(II)

Tan, K.W.; Ng, C.H.; Maah, M.J.; Ng, S.W.

doi:10.1107/S1600536808043973

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page m143

doi:10.1107/S1600536808043973

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(2,2′-Bipyridine-κ²N,N′)(4-hydroxy-2-oxidobenzaldehyde thiosemicarbazonato-κ³O²,N¹,S)zinc(II)

Kong Wai Tan,^a Chew Hee Ng,^b Mohd Jamil Maah ^a ^* and Seik Weng Ng ^a

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^bFaculty of Engineering and Science, Universiti Tunku Abdul Rahman, 53300 Kuala Lumpur, Malaysia
^*Correspondence e-mail: mjamil@um.edu.my

(Received 23 December 2008; accepted 25 December 2008; online 8 January 2009)

The Zn^II atom in the title compound, [Zn(C₈H₇N₃O₂S)(C₁₀H₈N₂)], is N,N′-chelated by the heterocycle and N,O,S-chelated by the doubly deprotonated Schiff base ligand in a distorted square-pyramidal environment. O—H⋯O and N—H⋯N hydrogen bonds link adjacent molecules into a layer structure.

Related literature

For the square-pyramidal 1,10-phenanthroline adduct, which exists as a monohydrated DMSO disolvate, see: Tan et al. (2009 ).

Experimental

Crystal data

[Zn(C₈H₇N₃O₂S)(C₁₀H₈N₂)]
M_r = 430.78
Monoclinic, P 2₁ /c
a = 16.1256 (4) Å
b = 7.0478 (2) Å
c = 17.6387 (5) Å
β = 113.646 (2)°
V = 1836.33 (9) Å³
Z = 4
Mo Kα radiation
μ = 1.48 mm⁻¹
T = 100 (2) K
0.10 × 0.04 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.867, T_max = 0.971
15773 measured reflections
4191 independent reflections
2919 reflections with I > 2σ(I)
R_int = 0.086

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.195
S = 1.04
4191 reflections
245 parameters
24 restraints
H-atom parameters constrained
Δρ_max = 0.88 e Å⁻³
Δρ_min = −0.96 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.84	1.85	2.625 (5)	153
N3—H32⋯N2ⁱⁱ	0.88	2.15	2.936 (7)	148
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808043973/tk2348sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808043973/tk2348Isup2.hkl

checkCIF report

Related literature top

For the square-pyramidal 1,10-phenanthroline adduct, which exists as a monohydrated DMSO disolvate, see: Tan et al. (2009).

Experimental top

Zinc acetate monohydrate (0.22 g, 1 mmol), 2,4-dihydroxybenzaldehyde thiosemicarbazone (0.21 g, 1 mmol) and 2,2'-bipyridine (0.16 g, 1 mmol) were heated in ethanol (40 ml). The compound that precipitated upon heating for 30 min was collected and recrystallized from DMF.

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 (Barbour, 2001) plot of Zn(C₈H₇N₃O₂S)(C₁₀H₈N₂) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radii.

(2,2'-Bipyridine-κ²N,N')(4-hydroxy-2-oxidobenzaldehyde thiosemicarbazonato-κ³O²,N¹,S)zinc(II) top

Crystal data top

[Zn(C₈H₇N₃O₂S)(C₁₀H₈N₂)]	F(000) = 880
M_r = 430.78	D_x = 1.558 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3053 reflections
a = 16.1256 (4) Å	θ = 2.3–26.2°
b = 7.0478 (2) Å	µ = 1.48 mm⁻¹
c = 17.6387 (5) Å	T = 100 K
β = 113.646 (2)°	Prism, yellow
V = 1836.33 (9) Å³	0.10 × 0.04 × 0.02 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	4191 independent reflections
Radiation source: fine-focus sealed tube	2919 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.086
ω scans	θ_max = 27.5°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→20
T_min = 0.867, T_max = 0.971	k = −9→9
15773 measured reflections	l = −21→22

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.195	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1071P)² + 3.3408P] where P = (F_o² + 2F_c²)/3
4191 reflections	(Δ/σ)_max = 0.001
245 parameters	Δρ_max = 0.88 e Å⁻³
24 restraints	Δρ_min = −0.96 e Å⁻³

Crystal data top

[Zn(C₈H₇N₃O₂S)(C₁₀H₈N₂)]	V = 1836.33 (9) Å³
M_r = 430.78	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.1256 (4) Å	µ = 1.48 mm⁻¹
b = 7.0478 (2) Å	T = 100 K
c = 17.6387 (5) Å	0.10 × 0.04 × 0.02 mm
β = 113.646 (2)°

Data collection top

Bruker SMART APEX diffractometer	4191 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2919 reflections with I > 2σ(I)
T_min = 0.867, T_max = 0.971	R_int = 0.086
15773 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	24 restraints
wR(F²) = 0.195	H-atom parameters constrained
S = 1.04	Δρ_max = 0.88 e Å⁻³
4191 reflections	Δρ_min = −0.96 e Å⁻³
245 parameters

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

	x	y	z	U_iso*/U_eq
Zn1	0.26010 (4)	0.61341 (9)	0.78222 (4)	0.0186 (2)
S1	0.35671 (10)	0.8297 (2)	0.75159 (9)	0.0239 (3)
O1	0.1393 (2)	0.4912 (5)	0.7423 (2)	0.0221 (8)
O2	−0.0804 (3)	−0.0017 (6)	0.6388 (2)	0.0238 (8)
H2	−0.0941	0.0325	0.6780	0.036*
N1	0.2953 (3)	0.4436 (7)	0.7058 (3)	0.0213 (10)
N2	0.3774 (3)	0.4754 (7)	0.6981 (3)	0.0226 (10)
N3	0.4867 (3)	0.6892 (7)	0.7112 (3)	0.0276 (11)
H31	0.5135	0.6021	0.6932	0.033*
H32	0.5107	0.8029	0.7242	0.033*
N4	0.3299 (3)	0.4781 (7)	0.8970 (3)	0.0276 (11)
N6	0.2340 (3)	0.7942 (6)	0.8656 (3)	0.0186 (9)
C1	0.1130 (4)	0.3300 (8)	0.7005 (3)	0.0198 (11)
C2	0.0305 (3)	0.2459 (8)	0.6918 (3)	0.0192 (11)
H2A	−0.0049	0.3053	0.7170	0.023*
C3	−0.0009 (4)	0.0790 (8)	0.6476 (3)	0.0199 (11)
C4	0.0493 (4)	−0.0115 (8)	0.6105 (3)	0.0250 (12)
H4	0.0276	−0.1248	0.5798	0.030*
C5	0.1305 (4)	0.0642 (8)	0.6187 (3)	0.0246 (12)
H5	0.1644	0.0017	0.5927	0.030*
C6	0.1660 (3)	0.2315 (7)	0.6641 (3)	0.0182 (10)
C7	0.2514 (4)	0.2930 (8)	0.6672 (3)	0.0210 (11)
H7	0.2788	0.2180	0.6388	0.025*
C8	0.4083 (4)	0.6481 (8)	0.7189 (3)	0.0233 (12)
C9	0.3807 (6)	0.3222 (11)	0.9082 (5)	0.0486 (19)
H9	0.3852	0.2632	0.8615	0.058*
C10	0.4268 (7)	0.2446 (14)	0.9857 (5)	0.068 (3)
H10	0.4631	0.1346	0.9924	0.082*
C11	0.4195 (6)	0.3282 (13)	1.0529 (5)	0.059 (2)
H11	0.4503	0.2752	1.1065	0.071*
C12	0.3680 (5)	0.4878 (11)	1.0429 (4)	0.0390 (16)
H12	0.3628	0.5480	1.0890	0.047*
C13	0.3235 (4)	0.5594 (9)	0.9635 (3)	0.0246 (12)
C14	0.2655 (4)	0.7348 (8)	0.9444 (3)	0.0235 (12)
C15	0.2450 (5)	0.8306 (10)	1.0037 (4)	0.0345 (15)
H15	0.2672	0.7861	1.0592	0.041*
C16	0.1917 (5)	0.9915 (11)	0.9804 (4)	0.0429 (18)
H16	0.1754	1.0573	1.0194	0.051*
C17	0.1624 (5)	1.0556 (9)	0.9000 (4)	0.0356 (15)
H17	0.1276	1.1684	0.8831	0.043*
C18	0.1848 (4)	0.9525 (8)	0.8448 (4)	0.0242 (12)
H18	0.1643	0.9961	0.7893	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0165 (3)	0.0207 (3)	0.0182 (3)	0.0020 (2)	0.0065 (2)	0.0029 (2)
S1	0.0208 (7)	0.0196 (7)	0.0340 (8)	0.0012 (5)	0.0139 (6)	0.0039 (5)
O1	0.0178 (19)	0.021 (2)	0.028 (2)	−0.0017 (15)	0.0101 (16)	−0.0024 (16)
O2	0.0186 (19)	0.027 (2)	0.025 (2)	−0.0039 (16)	0.0079 (16)	−0.0022 (16)
N1	0.018 (2)	0.026 (2)	0.021 (2)	−0.0014 (19)	0.0095 (19)	0.0022 (18)
N2	0.014 (2)	0.030 (3)	0.024 (2)	−0.0033 (19)	0.0094 (19)	−0.002 (2)
N3	0.022 (2)	0.025 (2)	0.043 (3)	−0.006 (2)	0.021 (2)	−0.005 (2)
N4	0.027 (3)	0.033 (3)	0.024 (2)	0.009 (2)	0.012 (2)	0.012 (2)
N6	0.016 (2)	0.019 (2)	0.019 (2)	0.0003 (17)	0.0052 (18)	0.0038 (17)
C1	0.020 (3)	0.019 (3)	0.019 (3)	0.002 (2)	0.007 (2)	0.004 (2)
C2	0.016 (2)	0.024 (3)	0.018 (2)	0.002 (2)	0.007 (2)	0.002 (2)
C3	0.015 (2)	0.023 (3)	0.018 (2)	0.001 (2)	0.002 (2)	0.006 (2)
C4	0.027 (3)	0.026 (3)	0.022 (3)	−0.002 (2)	0.010 (2)	0.000 (2)
C5	0.024 (3)	0.028 (3)	0.023 (3)	0.003 (2)	0.010 (2)	−0.003 (2)
C6	0.018 (3)	0.018 (3)	0.018 (2)	0.002 (2)	0.006 (2)	0.0031 (19)
C7	0.022 (3)	0.025 (3)	0.018 (3)	0.000 (2)	0.009 (2)	−0.001 (2)
C8	0.022 (3)	0.026 (3)	0.025 (3)	0.001 (2)	0.013 (2)	0.003 (2)
C9	0.059 (4)	0.049 (4)	0.048 (4)	0.032 (4)	0.032 (4)	0.022 (3)
C10	0.085 (6)	0.075 (5)	0.054 (5)	0.054 (5)	0.037 (4)	0.031 (4)
C11	0.065 (5)	0.076 (5)	0.039 (4)	0.037 (4)	0.024 (4)	0.032 (4)
C12	0.039 (4)	0.051 (4)	0.032 (3)	0.010 (3)	0.019 (3)	0.015 (3)
C13	0.020 (3)	0.031 (3)	0.021 (3)	0.000 (2)	0.006 (2)	0.007 (2)
C14	0.022 (3)	0.027 (3)	0.019 (3)	−0.007 (2)	0.005 (2)	−0.003 (2)
C15	0.042 (4)	0.036 (4)	0.021 (3)	0.001 (3)	0.008 (3)	−0.007 (2)
C16	0.053 (5)	0.041 (4)	0.029 (3)	0.004 (3)	0.011 (3)	−0.014 (3)
C17	0.040 (4)	0.028 (3)	0.034 (3)	0.010 (3)	0.010 (3)	−0.002 (3)
C18	0.020 (3)	0.023 (3)	0.023 (3)	−0.001 (2)	0.002 (2)	−0.001 (2)

Geometric parameters (Å, º) top

Zn1—O1	1.983 (4)	C4—C5	1.367 (8)
Zn1—N1	2.045 (5)	C4—H4	0.9500
Zn1—N4	2.109 (5)	C5—C6	1.412 (8)
Zn1—N6	2.112 (5)	C5—H5	0.9500
Zn1—S1	2.3911 (15)	C6—C7	1.423 (7)
S1—C8	1.746 (6)	C7—H7	0.9500
O1—C1	1.329 (7)	C9—C10	1.381 (10)
O2—C3	1.354 (6)	C9—H9	0.9500
O2—H2	0.8400	C10—C11	1.370 (12)
N1—C7	1.306 (7)	C10—H10	0.9500
N1—N2	1.403 (6)	C11—C12	1.367 (10)
N2—C8	1.310 (7)	C11—H11	0.9500
N3—C8	1.355 (7)	C12—C13	1.387 (8)
N3—H31	0.8800	C12—H12	0.9500
N3—H32	0.8800	C13—C14	1.505 (8)
N4—C9	1.338 (8)	C14—C15	1.393 (8)
N4—C13	1.346 (8)	C15—C16	1.382 (10)
N6—C18	1.333 (7)	C15—H15	0.9500
N6—C14	1.340 (7)	C16—C17	1.380 (9)
C1—C2	1.408 (7)	C16—H16	0.9500
C1—C6	1.437 (7)	C17—C18	1.373 (9)
C2—C3	1.389 (8)	C17—H17	0.9500
C2—H2A	0.9500	C18—H18	0.9500
C3—C4	1.385 (8)

O1—Zn1—N1	90.29 (16)	C6—C5—H5	118.7
O1—Zn1—N4	102.37 (18)	C5—C6—C7	116.2 (5)
N1—Zn1—N4	100.70 (19)	C5—C6—C1	118.6 (5)
O1—Zn1—N6	93.82 (16)	C7—C6—C1	125.1 (5)
N1—Zn1—N6	175.77 (18)	N1—C7—C6	125.5 (5)
N4—Zn1—N6	77.46 (19)	N1—C7—H7	117.2
O1—Zn1—S1	146.42 (12)	C6—C7—H7	117.2
N1—Zn1—S1	81.14 (13)	N2—C8—N3	115.8 (5)
N4—Zn1—S1	111.10 (15)	N2—C8—S1	126.5 (4)
N6—Zn1—S1	95.92 (13)	N3—C8—S1	117.6 (4)
C8—S1—Zn1	92.73 (19)	N4—C9—C10	121.7 (7)
C1—O1—Zn1	128.1 (3)	N4—C9—H9	119.1
C3—O2—H2	109.5	C10—C9—H9	119.1
C7—N1—N2	114.5 (5)	C11—C10—C9	119.2 (7)
C7—N1—Zn1	125.7 (4)	C11—C10—H10	120.4
N2—N1—Zn1	119.5 (3)	C9—C10—H10	120.4
C8—N2—N1	112.9 (5)	C10—C11—C12	120.0 (7)
C8—N3—H31	120.0	C10—C11—H11	120.0
C8—N3—H32	120.0	C12—C11—H11	120.0
H31—N3—H32	120.0	C11—C12—C13	118.1 (7)
C9—N4—C13	118.5 (5)	C11—C12—H12	121.0
C9—N4—Zn1	124.9 (5)	C13—C12—H12	121.0
C13—N4—Zn1	116.5 (4)	N4—C13—C12	122.4 (6)
C18—N6—C14	118.9 (5)	N4—C13—C14	114.3 (5)
C18—N6—Zn1	125.2 (4)	C12—C13—C14	123.2 (6)
C14—N6—Zn1	115.8 (4)	N6—C14—C15	121.5 (6)
O1—C1—C2	119.8 (5)	N6—C14—C13	115.6 (5)
O1—C1—C6	123.2 (5)	C15—C14—C13	122.9 (5)
C2—C1—C6	117.0 (5)	C16—C15—C14	118.7 (6)
C3—C2—C1	122.2 (5)	C16—C15—H15	120.6
C3—C2—H2A	118.9	C14—C15—H15	120.6
C1—C2—H2A	118.9	C17—C16—C15	119.3 (6)
O2—C3—C4	117.3 (5)	C17—C16—H16	120.3
O2—C3—C2	122.4 (5)	C15—C16—H16	120.3
C4—C3—C2	120.3 (5)	C18—C17—C16	118.5 (6)
C5—C4—C3	119.2 (5)	C18—C17—H17	120.8
C5—C4—H4	120.4	C16—C17—H17	120.8
C3—C4—H4	120.4	N6—C18—C17	123.0 (5)
C4—C5—C6	122.6 (5)	N6—C18—H18	118.5
C4—C5—H5	118.7	C17—C18—H18	118.5

O1—Zn1—S1—C8	−95.8 (3)	C4—C5—C6—C1	−2.5 (8)
N1—Zn1—S1—C8	−18.8 (2)	O1—C1—C6—C5	−178.1 (5)
N4—Zn1—S1—C8	79.3 (2)	C2—C1—C6—C5	3.3 (7)
N6—Zn1—S1—C8	158.1 (2)	O1—C1—C6—C7	−0.7 (8)
N1—Zn1—O1—C1	15.3 (4)	C2—C1—C6—C7	−179.2 (5)
N4—Zn1—O1—C1	−85.8 (4)	N2—N1—C7—C6	−178.8 (5)
N6—Zn1—O1—C1	−163.8 (4)	Zn1—N1—C7—C6	7.3 (8)
S1—Zn1—O1—C1	89.5 (5)	C5—C6—C7—N1	180.0 (5)
O1—Zn1—N1—C7	−13.1 (5)	C1—C6—C7—N1	2.5 (9)
N4—Zn1—N1—C7	89.5 (5)	N1—N2—C8—N3	−178.7 (5)
S1—Zn1—N1—C7	−160.5 (5)	N1—N2—C8—S1	−1.0 (7)
O1—Zn1—N1—N2	173.2 (4)	Zn1—S1—C8—N2	17.3 (5)
N4—Zn1—N1—N2	−84.1 (4)	Zn1—S1—C8—N3	−165.0 (4)
S1—Zn1—N1—N2	25.8 (4)	C13—N4—C9—C10	−0.5 (12)
C7—N1—N2—C8	163.9 (5)	Zn1—N4—C9—C10	178.0 (7)
Zn1—N1—N2—C8	−21.8 (6)	N4—C9—C10—C11	0.7 (15)
O1—Zn1—N4—C9	92.1 (6)	C9—C10—C11—C12	−0.8 (16)
N1—Zn1—N4—C9	−0.5 (6)	C10—C11—C12—C13	0.6 (13)
N6—Zn1—N4—C9	−176.7 (6)	C9—N4—C13—C12	0.3 (10)
S1—Zn1—N4—C9	−85.1 (6)	Zn1—N4—C13—C12	−178.3 (5)
O1—Zn1—N4—C13	−89.4 (4)	C9—N4—C13—C14	179.5 (6)
N1—Zn1—N4—C13	177.9 (4)	Zn1—N4—C13—C14	0.9 (6)
N6—Zn1—N4—C13	1.8 (4)	C11—C12—C13—N4	−0.4 (10)
S1—Zn1—N4—C13	93.4 (4)	C11—C12—C13—C14	−179.5 (7)
O1—Zn1—N6—C18	−78.4 (4)	C18—N6—C14—C15	2.6 (8)
N4—Zn1—N6—C18	179.8 (5)	Zn1—N6—C14—C15	−173.4 (5)
S1—Zn1—N6—C18	69.4 (4)	C18—N6—C14—C13	−177.6 (5)
O1—Zn1—N6—C14	97.3 (4)	Zn1—N6—C14—C13	6.4 (6)
N4—Zn1—N6—C14	−4.6 (4)	N4—C13—C14—N6	−4.9 (7)
S1—Zn1—N6—C14	−114.9 (4)	C12—C13—C14—N6	174.3 (6)
Zn1—O1—C1—C2	167.2 (4)	N4—C13—C14—C15	174.9 (6)
Zn1—O1—C1—C6	−11.3 (7)	C12—C13—C14—C15	−5.9 (9)
O1—C1—C2—C3	179.0 (5)	N6—C14—C15—C16	−0.7 (10)
C6—C1—C2—C3	−2.4 (8)	C13—C14—C15—C16	179.5 (6)
C1—C2—C3—O2	−179.6 (5)	C14—C15—C16—C17	−1.7 (11)
C1—C2—C3—C4	0.3 (8)	C15—C16—C17—C18	2.3 (11)
O2—C3—C4—C5	−179.3 (5)	C14—N6—C18—C17	−2.0 (9)
C2—C3—C4—C5	0.7 (8)	Zn1—N6—C18—C17	173.5 (5)
C3—C4—C5—C6	0.4 (9)	C16—C17—C18—N6	−0.5 (10)
C4—C5—C6—C7	179.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.84	1.85	2.625 (5)	153
N3—H32···N2ⁱⁱ	0.88	2.15	2.936 (7)	148

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

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₇N₃O₂S)(C₁₀H₈N₂)]
M_r	430.78
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	16.1256 (4), 7.0478 (2), 17.6387 (5)
β (°)	113.646 (2)
V (Å³)	1836.33 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.48
Crystal size (mm)	0.10 × 0.04 × 0.02

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.867, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	15773, 4191, 2919
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.195, 1.04
No. of reflections	4191
No. of parameters	245
No. of restraints	24
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.88, −0.96

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
O2—H2···O1ⁱ	0.84	1.85	2.625 (5)	153
N3—H32···N2ⁱⁱ	0.88	2.15	2.936 (7)	148

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

Acknowledgements

The authors thank the Ministry of Science and Technology (grant No. ESc 02-02-11-SF0033) for supporting this study. KWT thanks the Ministry of Higher Education for an SLAI scholarship.

References

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
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
Tan, K. W., Ng, C. H., Maah, M. J. & Ng, S. W. (2009). Acta Cryst. E65, m61–m62. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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