8-Hy­droxy-2-methyl­quinolinium tetra­chlorido(pyridine-2-carboxyl­ato-κ2N,O)stannate(IV)

Najafi, E.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536811001942

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page m240

doi:10.1107/S1600536811001942

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8-Hydroxy-2-methylquinolinium tetrachlorido(pyridine-2-carboxylato-κ²N,O)stannate(IV)

Ezzatollah Najafi,^a Mostafa M. Amini ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 8 January 2011; accepted 12 January 2011; online 22 January 2011)

In the reaction of pyridine-2-carboxylic acid and stannic chloride in the presence of 2-methyl-8-hydroxyquinoline, the 2-methyl-8-hydroxyquinoline is protonated, yielding the title salt, (C₁₀H₁₀NO)[SnCl₄(C₆H₄NO₂)]. The Sn^IV atom in the anion is N,O-chelated by a pyridine-2-carboxylate in a cis-SnNOCl₄ octahedral geometry. The cation is linked to the anion by an O—H⋯O hydrogen bond.

Related literature

For other 8-hydroxy-2-methylquinolinium salts, see: Najafi et al. (2010 ); Sattarzadeh et al. (2009 ).

Experimental

Crystal data

(C₁₀H₁₀NO)[SnCl₄(C₆H₄NO₂)]
M_r = 542.78
Monoclinic, P 2₁ /c
a = 11.5188 (2) Å
b = 11.1971 (2) Å
c = 15.0257 (2) Å
β = 94.563 (2)°
V = 1931.83 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.90 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010 ) T_min = 0.600, T_max = 0.703
9737 measured reflections
4304 independent reflections
3686 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.064
S = 1.04
4304 reflections
242 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.62 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.84 (3)	1.86 (1)	2.686 (3)	168 (3)

Data collection: CrysAlis PRO (Agilent Technologies, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: 10.1107/S1600536811001942/si2327sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811001942/si2327Isup2.hkl

checkCIF report

Comment top

The direct synthesis of a potentially chelating amino-carboxylic acid with stannic tetrachloride has not been reported. Pyridine-2-carboxylic acid yields a number of derivatives with organotin compounds; these are either synthesized by condensing the amino-carboxylic acids with an organotin oxide/hydroxide or by reacting the amino-carboxylic acids with an organotin chloride in the presence of a proton abstractor. With the latter route, the product may be an organostannate in which the pyridine-2-carboxylate chelates to the chlorine-bonded tin atom. In the reaction of pyridine-2-carboxylic acid and stannic chloride in the presence of 2-methyl-8-hydroxyquinoline, the 2-methyl-8-hydroxyquinoline is protonated to yield the salt, [C₁₀H₁₀NO₂]⁺ [SnCl₄(C₆H₄NO₂)]^- (Scheme I, Fig. 1). The tin atom in the anion is N,O-chelated by a pyridine-2-carboxylate in an octahedral geometry. The cation is linked to the anion by an O–H···O hydrogen bond (Table 1). The cation been observed in a similar reaction with zinc salts (Najafi et al., 2010; Sattarzadeh et al., 2009).

Related literature top

For other 8-hydroxy-2-methylquinolinium salts, see: Najafi et al. (2010); Sattarzadeh et al. (2009).

Experimental top

Stannic chloride pentahydrate (0.35 g, 1 mmol), pyridine-2-carboxylic acid (0.13 g, 1 mmol) and 2-methyl-8-hydroxyquinoline (0.16 g, 1 mmol) were loaded into a convection tube; the tube was filled with dry methanol and kept at 333 K. Beige crystals were collected from the side arm after several days.

Computing details top

Data collection: CrysAlis PRO (Agilent Technologies, 2010); cell refinement: CrysAlis PRO (Agilent Technologies, 2010); data reduction: CrysAlis PRO (Agilent Technologies, 2010); 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. Thermal ellipsoid plot (Barbour, 2001) of [C₁₀H₁₀NO₂]⁺ [SnCl₄(C₆H₄NO₂)]^– at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

8-Hydroxy-2-methylquinolinium tetrachlorido(pyridine-2-carboxylato-κ²N,O)stannate(IV) top

Crystal data top

(C₁₀H₁₀NO)[SnCl₄(C₆H₄NO₂)]	F(000) = 1064
M_r = 542.78	D_x = 1.866 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5318 reflections
a = 11.5188 (2) Å	θ = 2.3–29.2°
b = 11.1971 (2) Å	µ = 1.90 mm⁻¹
c = 15.0257 (2) Å	T = 100 K
β = 94.563 (2)°	Prism, beige
V = 1931.83 (5) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4304 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3686 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.031
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.5°
ω scans	h = −13→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010)	k = −9→14
T_min = 0.600, T_max = 0.703	l = −19→18
9737 measured reflections

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0264P)²] where P = (F_o² + 2F_c²)/3
4304 reflections	(Δ/σ)_max = 0.001
242 parameters	Δρ_max = 0.54 e Å⁻³
2 restraints	Δρ_min = −0.62 e Å⁻³

Crystal data top

(C₁₀H₁₀NO)[SnCl₄(C₆H₄NO₂)]	V = 1931.83 (5) Å³
M_r = 542.78	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.5188 (2) Å	µ = 1.90 mm⁻¹
b = 11.1971 (2) Å	T = 100 K
c = 15.0257 (2) Å	0.30 × 0.25 × 0.20 mm
β = 94.563 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4304 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010)	3686 reflections with I > 2σ(I)
T_min = 0.600, T_max = 0.703	R_int = 0.031
9737 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	2 restraints
wR(F²) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.54 e Å⁻³
4304 reflections	Δρ_min = −0.62 e Å⁻³
242 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.739358 (15)	0.452510 (16)	0.285941 (11)	0.01301 (7)
Cl1	0.63844 (6)	0.27357 (6)	0.32327 (4)	0.01928 (15)
Cl2	0.57101 (6)	0.54218 (6)	0.21479 (4)	0.01787 (15)
Cl3	0.81600 (6)	0.36052 (6)	0.15995 (4)	0.02070 (16)
Cl4	0.85945 (6)	0.62635 (6)	0.26734 (4)	0.01903 (15)
O1	0.70258 (16)	0.52449 (16)	0.41026 (12)	0.0163 (4)
O2	0.75372 (17)	0.52641 (17)	0.55626 (12)	0.0202 (4)
O3	0.66210 (17)	0.64322 (18)	0.69025 (12)	0.0206 (4)
H3	0.690 (3)	0.616 (3)	0.6447 (13)	0.031*
N1	0.88239 (18)	0.38362 (19)	0.38018 (13)	0.0131 (5)
N2	0.58299 (19)	0.7069 (2)	0.84655 (14)	0.0154 (5)
H2	0.553 (2)	0.732 (3)	0.7947 (11)	0.023*
C1	0.7667 (2)	0.4919 (2)	0.48003 (17)	0.0153 (6)
C2	0.8656 (2)	0.4085 (2)	0.46593 (17)	0.0138 (5)
C3	0.9373 (2)	0.3617 (2)	0.53524 (18)	0.0180 (6)
H3A	0.9239	0.3787	0.5955	0.022*
C4	1.0291 (2)	0.2895 (2)	0.51533 (18)	0.0196 (6)
H4	1.0788	0.2552	0.5619	0.024*
C5	1.0481 (2)	0.2677 (3)	0.42687 (18)	0.0191 (6)
H5	1.1125	0.2207	0.4119	0.023*
C6	0.9718 (2)	0.3155 (2)	0.36087 (18)	0.0174 (6)
H6	0.9832	0.2994	0.3001	0.021*
C8	0.7199 (2)	0.5982 (2)	0.76441 (17)	0.0155 (6)
C9	0.8168 (2)	0.5276 (2)	0.76669 (18)	0.0194 (6)
H9	0.8488	0.5065	0.7125	0.023*
C10	0.8698 (2)	0.4858 (3)	0.84826 (19)	0.0205 (6)
H10	0.9385	0.4388	0.8483	0.025*
C11	0.8247 (2)	0.5114 (3)	0.92770 (18)	0.0203 (6)
H11	0.8598	0.4796	0.9820	0.024*
C12	0.7261 (2)	0.5851 (2)	0.92813 (18)	0.0161 (6)
C13	0.6761 (2)	0.6306 (2)	0.84629 (17)	0.0149 (6)
C14	0.6737 (2)	0.6196 (3)	1.00615 (18)	0.0211 (6)
H14	0.7031	0.5884	1.0623	0.025*
C15	0.5820 (2)	0.6965 (3)	1.00250 (18)	0.0203 (6)
H15	0.5489	0.7192	1.0559	0.024*
C16	0.5358 (2)	0.7424 (3)	0.91984 (18)	0.0187 (6)
C17	0.4394 (3)	0.8305 (3)	0.91255 (19)	0.0237 (7)
H17A	0.4068	0.8350	0.8504	0.036*
H17B	0.4692	0.9091	0.9318	0.036*
H17C	0.3786	0.8056	0.9506	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01389 (11)	0.01420 (11)	0.01113 (10)	0.00037 (7)	0.00216 (7)	−0.00015 (7)
Cl1	0.0187 (3)	0.0184 (3)	0.0206 (3)	−0.0032 (3)	0.0005 (3)	0.0025 (3)
Cl2	0.0166 (3)	0.0192 (3)	0.0174 (3)	0.0018 (3)	−0.0008 (3)	0.0015 (3)
Cl3	0.0250 (4)	0.0234 (4)	0.0142 (3)	0.0023 (3)	0.0047 (3)	−0.0034 (3)
Cl4	0.0202 (3)	0.0173 (3)	0.0198 (3)	−0.0032 (3)	0.0028 (3)	0.0020 (3)
O1	0.0187 (10)	0.0195 (10)	0.0107 (9)	0.0043 (8)	0.0020 (8)	−0.0013 (8)
O2	0.0233 (11)	0.0247 (11)	0.0132 (10)	−0.0022 (9)	0.0048 (8)	−0.0031 (8)
O3	0.0230 (11)	0.0263 (11)	0.0125 (10)	0.0091 (9)	0.0014 (8)	−0.0013 (8)
N1	0.0141 (11)	0.0139 (11)	0.0115 (11)	−0.0029 (10)	0.0018 (9)	−0.0009 (9)
N2	0.0163 (12)	0.0177 (12)	0.0121 (11)	0.0015 (10)	0.0001 (9)	−0.0005 (10)
C1	0.0180 (14)	0.0147 (14)	0.0138 (14)	−0.0040 (12)	0.0048 (11)	−0.0017 (11)
C2	0.0145 (13)	0.0124 (13)	0.0148 (13)	−0.0044 (11)	0.0024 (10)	0.0004 (11)
C3	0.0237 (15)	0.0145 (14)	0.0158 (14)	−0.0030 (12)	0.0020 (12)	−0.0004 (11)
C4	0.0225 (15)	0.0165 (14)	0.0190 (14)	0.0006 (12)	−0.0044 (12)	0.0017 (12)
C5	0.0164 (14)	0.0181 (14)	0.0224 (15)	0.0020 (12)	−0.0004 (11)	−0.0031 (12)
C6	0.0153 (14)	0.0170 (14)	0.0204 (15)	0.0007 (12)	0.0038 (11)	−0.0026 (12)
C8	0.0171 (14)	0.0137 (13)	0.0159 (13)	−0.0030 (12)	0.0017 (11)	−0.0011 (11)
C9	0.0227 (15)	0.0192 (15)	0.0170 (14)	0.0009 (12)	0.0058 (12)	−0.0034 (12)
C10	0.0165 (14)	0.0184 (14)	0.0269 (16)	0.0027 (12)	0.0030 (12)	0.0015 (12)
C11	0.0220 (15)	0.0211 (15)	0.0172 (15)	0.0015 (13)	−0.0015 (12)	0.0045 (12)
C12	0.0155 (14)	0.0151 (14)	0.0178 (14)	−0.0030 (12)	0.0014 (11)	0.0010 (11)
C13	0.0152 (14)	0.0144 (14)	0.0152 (13)	−0.0018 (11)	0.0024 (11)	0.0003 (11)
C14	0.0194 (15)	0.0283 (17)	0.0155 (14)	−0.0055 (13)	0.0007 (11)	0.0025 (12)
C15	0.0226 (15)	0.0265 (16)	0.0127 (13)	−0.0029 (13)	0.0079 (11)	−0.0057 (12)
C16	0.0168 (14)	0.0207 (15)	0.0195 (14)	−0.0050 (12)	0.0063 (11)	−0.0049 (12)
C17	0.0224 (16)	0.0277 (17)	0.0219 (15)	0.0018 (13)	0.0064 (12)	−0.0050 (13)

Geometric parameters (Å, º) top

Sn1—O1	2.1081 (17)	C5—C6	1.380 (4)
Sn1—N1	2.223 (2)	C5—H5	0.9500
Sn1—Cl2	2.3626 (7)	C6—H6	0.9500
Sn1—Cl3	2.3854 (7)	C8—C9	1.365 (4)
Sn1—Cl1	2.4050 (7)	C8—C13	1.414 (4)
Sn1—Cl4	2.4171 (7)	C9—C10	1.405 (4)
O1—C1	1.286 (3)	C9—H9	0.9500
O2—C1	1.229 (3)	C10—C11	1.369 (4)
O3—C8	1.350 (3)	C10—H10	0.9500
O3—H3	0.84 (3)	C11—C12	1.404 (4)
N1—C6	1.332 (3)	C11—H11	0.9500
N1—C2	1.347 (3)	C12—C13	1.411 (4)
N2—C16	1.327 (3)	C12—C14	1.414 (4)
N2—C13	1.371 (3)	C14—C15	1.361 (4)
N2—H2	0.88 (3)	C14—H14	0.9500
C1—C2	1.502 (4)	C15—C16	1.409 (4)
C2—C3	1.380 (4)	C15—H15	0.9500
C3—C4	1.382 (4)	C16—C17	1.483 (4)
C3—H3A	0.9500	C17—H17A	0.9800
C4—C5	1.386 (4)	C17—H17B	0.9800
C4—H4	0.9500	C17—H17C	0.9800

O1—Sn1—N1	76.07 (7)	C4—C5—H5	120.6
O1—Sn1—Cl2	91.31 (5)	N1—C6—C5	121.7 (3)
N1—Sn1—Cl2	167.32 (6)	N1—C6—H6	119.2
O1—Sn1—Cl3	168.94 (5)	C5—C6—H6	119.2
N1—Sn1—Cl3	93.06 (6)	O3—C8—C9	125.9 (2)
Cl2—Sn1—Cl3	99.60 (2)	O3—C8—C13	115.8 (2)
O1—Sn1—Cl1	88.68 (5)	C9—C8—C13	118.3 (2)
N1—Sn1—Cl1	84.83 (6)	C8—C9—C10	120.8 (3)
Cl2—Sn1—Cl1	93.73 (2)	C8—C9—H9	119.6
Cl3—Sn1—Cl1	92.39 (2)	C10—C9—H9	119.6
O1—Sn1—Cl4	87.23 (5)	C11—C10—C9	121.5 (3)
N1—Sn1—Cl4	87.20 (6)	C11—C10—H10	119.3
Cl2—Sn1—Cl4	93.56 (2)	C9—C10—H10	119.3
Cl3—Sn1—Cl4	90.27 (2)	C10—C11—C12	119.3 (3)
Cl1—Sn1—Cl4	171.72 (2)	C10—C11—H11	120.3
C1—O1—Sn1	118.10 (17)	C12—C11—H11	120.3
C8—O3—H3	110 (2)	C13—C12—C11	118.9 (2)
C6—N1—C2	119.9 (2)	C13—C12—C14	116.9 (2)
C6—N1—Sn1	127.34 (17)	C11—C12—C14	124.3 (3)
C2—N1—Sn1	112.47 (17)	N2—C13—C12	119.2 (2)
C16—N2—C13	124.1 (2)	N2—C13—C8	119.7 (2)
C16—N2—H2	119 (2)	C12—C13—C8	121.1 (2)
C13—N2—H2	117 (2)	C15—C14—C12	121.4 (3)
O2—C1—O1	124.5 (3)	C15—C14—H14	119.3
O2—C1—C2	118.5 (2)	C12—C14—H14	119.3
O1—C1—C2	117.0 (2)	C14—C15—C16	120.3 (3)
N1—C2—C3	121.4 (3)	C14—C15—H15	119.9
N1—C2—C1	115.6 (2)	C16—C15—H15	119.9
C3—C2—C1	123.0 (2)	N2—C16—C15	118.1 (3)
C2—C3—C4	118.7 (3)	N2—C16—C17	119.5 (2)
C2—C3—H3A	120.6	C15—C16—C17	122.4 (2)
C4—C3—H3A	120.6	C16—C17—H17A	109.5
C3—C4—C5	119.5 (3)	C16—C17—H17B	109.5
C3—C4—H4	120.2	H17A—C17—H17B	109.5
C5—C4—H4	120.2	C16—C17—H17C	109.5
C6—C5—C4	118.7 (3)	H17A—C17—H17C	109.5
C6—C5—H5	120.6	H17B—C17—H17C	109.5

N1—Sn1—O1—C1	−5.35 (18)	C3—C4—C5—C6	−2.3 (4)
Cl2—Sn1—O1—C1	173.35 (18)	C2—N1—C6—C5	0.8 (4)
Cl3—Sn1—O1—C1	−16.0 (4)	Sn1—N1—C6—C5	−172.80 (19)
Cl1—Sn1—O1—C1	79.65 (18)	C4—C5—C6—N1	1.4 (4)
Cl4—Sn1—O1—C1	−93.15 (18)	O3—C8—C9—C10	180.0 (3)
O1—Sn1—N1—C6	−178.3 (2)	C13—C8—C9—C10	1.6 (4)
Cl2—Sn1—N1—C6	175.77 (18)	C8—C9—C10—C11	1.8 (5)
Cl3—Sn1—N1—C6	−0.3 (2)	C9—C10—C11—C12	−2.7 (4)
Cl1—Sn1—N1—C6	91.8 (2)	C10—C11—C12—C13	0.2 (4)
Cl4—Sn1—N1—C6	−90.5 (2)	C10—C11—C12—C14	−178.6 (3)
O1—Sn1—N1—C2	7.74 (17)	C16—N2—C13—C12	0.4 (4)
Cl2—Sn1—N1—C2	1.8 (4)	C16—N2—C13—C8	−180.0 (3)
Cl3—Sn1—N1—C2	−174.30 (17)	C11—C12—C13—N2	−177.1 (3)
Cl1—Sn1—N1—C2	−82.18 (17)	C14—C12—C13—N2	1.7 (4)
Cl4—Sn1—N1—C2	95.58 (17)	C11—C12—C13—C8	3.3 (4)
Sn1—O1—C1—O2	−179.3 (2)	C14—C12—C13—C8	−177.9 (2)
Sn1—O1—C1—C2	2.3 (3)	O3—C8—C13—N2	−2.3 (4)
C6—N1—C2—C3	−2.0 (4)	C9—C8—C13—N2	176.3 (3)
Sn1—N1—C2—C3	172.4 (2)	O3—C8—C13—C12	177.3 (2)
C6—N1—C2—C1	176.5 (2)	C9—C8—C13—C12	−4.1 (4)
Sn1—N1—C2—C1	−9.1 (3)	C13—C12—C14—C15	−2.4 (4)
O2—C1—C2—N1	−173.5 (2)	C11—C12—C14—C15	176.4 (3)
O1—C1—C2—N1	5.0 (4)	C12—C14—C15—C16	0.9 (4)
O2—C1—C2—C3	5.0 (4)	C13—N2—C16—C15	−1.9 (4)
O1—C1—C2—C3	−176.5 (2)	C13—N2—C16—C17	176.6 (3)
N1—C2—C3—C4	1.1 (4)	C14—C15—C16—N2	1.2 (4)
C1—C2—C3—C4	−177.3 (3)	C14—C15—C16—C17	−177.2 (3)
C2—C3—C4—C5	1.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.84 (3)	1.86 (1)	2.686 (3)	168 (3)

Experimental details

Crystal data
Chemical formula	(C₁₀H₁₀NO)[SnCl₄(C₆H₄NO₂)]
M_r	542.78
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.5188 (2), 11.1971 (2), 15.0257 (2)
β (°)	94.563 (2)
V (Å³)	1931.83 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.90
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent Technologies, 2010)
T_min, T_max	0.600, 0.703
No. of measured, independent and observed [I > 2σ(I)] reflections	9737, 4304, 3686
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.064, 1.04
No. of reflections	4304
No. of parameters	242
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.62

Computer programs: CrysAlis PRO (Agilent Technologies, 2010), 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···O2	0.84 (3)	1.86 (1)	2.686 (3)	168 (3)

Acknowledgements

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

References

Agilent Technologies (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Najafi, E., Amini, M. M. & Ng, S. W. (2010). Acta Cryst. E66, m1276. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sattarzadeh, E., Mohammadnezhad, G., Amini, M. M. & Ng, S. W. (2009). Acta Cryst. E65, m553. Web of Science CSD CrossRef IUCr Journals Google Scholar
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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