Di-μ2-methano­lato-bis­(μ-4-methyl-5-sulfanyl­idene-4,5-dihydro-1H-1,2,4-triazolido-κ2N1:N2)di-μ3-oxido-tetra­kis­[dimethyl­tin(IV)]

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

doi:10.1107/S1600536811001905

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page m242

doi:10.1107/S1600536811001905

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Di-μ₂-methanolato-bis(μ-4-methyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazolido-κ²N¹:N²)di-μ₃-oxido-tetrakis[dimethyltin(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 9 January 2011; accepted 12 January 2011; online 22 January 2011)

The title distannoxane, [Sn₄(CH₃)₈(C₃H₄N₃S)₂(CH₃O)₂O₂], lies about a center of inversion; the tetranuclear molecule features a three-rung-staircase Sn₄O₄ core in which the two crystallographically independent Sn^IV atoms are bridged by the triazolide group. The negatively charged N atom of the triazolide group binds to the terminal Sn atom at a shorter distance [Sn—N = 2.239 (2) Å] compared with the neutral N atom that binds to the central Sn atom [Sn← N = 2.757 (3) Å]. The oxide O atom is three-coordinate whereas the methanolate O atom is two-coordinate. The terminal Sn atom is five-coordinate in a cis-C₃SnNO trigonal–bipyramidal environment, whereas the central Sn atom is six-coordinate in a C₂SnNO₃ skew-trapezoidal–bipyramidal geometry.

Related literature

For related distannoxanes, see: Ma et al. (2007 ); Yu et al. (2006 ).

Experimental

Crystal data

[Sn₄(CH₃)₈(C₃H₄N₃S)₂(CH₃O)₂O₂]
M_r = 917.40
Triclinic, $[P \overline 1]$
a = 7.3693 (6) Å
b = 9.3457 (8) Å
c = 11.9930 (9) Å
α = 71.681 (7)°
β = 76.780 (6)°
γ = 77.118 (7)°
V = 753.07 (11) Å³
Z = 1
Mo Kα radiation
μ = 3.45 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent Technologies SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010 ) T_min = 0.425, T_max = 0.546
5805 measured reflections
3328 independent reflections
2919 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.047
S = 0.98
3328 reflections
152 parameters
H-atom parameters constrained
Δρ_max = 0.83 e Å⁻³
Δρ_min = −0.77 e Å⁻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/S1600536811001905/xu5141sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811001905/xu5141Isup2.hkl

checkCIF report

Comment top

The title compound (Scheme I, Fig. 1), a distannoxane, was the unexpected product from an attempt at synthesizing a dimethyltin 4,-methyl-4H-1,2,4-triazol-3-thiolate that possesses a tin-sulfur linkage. In the reaction of diorganotin oxides with organic acids (particularly carboxylic acid), tetranuclear distannoxanes are sometimes formed; these compounds have four organic groups. In the present reaction, two of the four organic groups are replaced by methoxide groups.

Tetranuclear Sn₄O₂(CH₃)₈(CH₃O)₂(C₃H₄N₃S)₂ distannoxane lies about a center-of-inversion; the molecule features a three-rung-staircase Sn₄O₄ core in which two Sn atoms are bridged by the C₃H₄N₃S triazolide group. The negatively-charged N atom of the group binds to the terminal Sn atom at a shorter distance [Sn–N 2.239 (2) Å] compared with the neutral N atom that binds to the central Sn atom [Sn←N 2.757 (2) Å]. The oxo O atom is three-coordinate whereas the methanolate O atom is two-coordinate. The terminal Sn atom is five-coordinate in a cis-C₃SnNO trigonal bipyramid whereas the central Sn atom is six-coordinate in a C₂SnNO₃ skew-trazepoidal bipyramidal geometry.

The formation of similar distannoxanes that feature bridging triazolides are limited to the 4-(benzylideneamino)-3-methyl-5-thioxo-1,2,4-triazolide, 4-(2-furylmethylene)amino-3-methyl-5-thioxo-1,2,4-triazolide, 4-(2-thienylmethylene)amino-3-methyl-5-thioxo-1,2,4-triazolide and 5-(2-thienylmethylene)amino-2-thioxo-1,3,4-thiadiazolates only (Ma et al., 2007; Yu et al., 2006).

Related literature top

For related distannoxanes, see: Ma et al. (2007); Yu et al. (2006).

Experimental top

Dimethyltin diisothiocyanate (1 mmol), 4-methyl-4H-1,2,4-triazole-3-thiol (1 mmol) and 1,10-phenanthroline (1 mmol) were loaded into a convection tube; several drops of triethylamine were added. The tube was filled with dry methanol and kept at 333 K. Colorless 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 Sn₄O₂(CH₃)₈(CH₃O)₂(C₃H₄N₃S)₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Di-µ₂-methanolato-bis(µ-4-methyl-5-sulfanylidene-4,5-dihydro-1H- 1,2,4-triazolido-κ²N¹:N²)di-µ₃-oxido- tetrakis[dimethyltin(IV)] top

Crystal data top

[Sn₄(CH₃)₈(C₃H₄N₃S)₂(CH₃O)₂O₂]	Z = 1
M_r = 917.40	F(000) = 440
Triclinic, P1	D_x = 2.023 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3693 (6) Å	Cell parameters from 3945 reflections
b = 9.3457 (8) Å	θ = 2.3–29.2°
c = 11.9930 (9) Å	µ = 3.45 mm⁻¹
α = 71.681 (7)°	T = 100 K
β = 76.780 (6)°	Block, colorless
γ = 77.118 (7)°	0.30 × 0.25 × 0.20 mm
V = 753.07 (11) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3328 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2919 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.029
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.3°
ω scans	h = −7→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −12→11
T_min = 0.425, T_max = 0.546	l = −14→15
5805 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.024	H-atom parameters constrained
wR(F²) = 0.047	w = 1/[σ²(F_o²) + (0.0144P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max = 0.001
3328 reflections	Δρ_max = 0.83 e Å⁻³
152 parameters	Δρ_min = −0.77 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0086 (3)

Crystal data top

[Sn₄(CH₃)₈(C₃H₄N₃S)₂(CH₃O)₂O₂]	γ = 77.118 (7)°
M_r = 917.40	V = 753.07 (11) Å³
Triclinic, P1	Z = 1
a = 7.3693 (6) Å	Mo Kα radiation
b = 9.3457 (8) Å	µ = 3.45 mm⁻¹
c = 11.9930 (9) Å	T = 100 K
α = 71.681 (7)°	0.30 × 0.25 × 0.20 mm
β = 76.780 (6)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3328 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2919 reflections with I > 2σ(I)
T_min = 0.425, T_max = 0.546	R_int = 0.029
5805 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.047	H-atom parameters constrained
S = 0.98	Δρ_max = 0.83 e Å⁻³
3328 reflections	Δρ_min = −0.77 e Å⁻³
152 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.23531 (3)	0.50079 (2)	0.258264 (16)	0.01270 (7)
Sn2	0.57195 (3)	0.31342 (2)	0.021831 (16)	0.01318 (7)
S1	0.14046 (14)	0.21699 (10)	0.54808 (7)	0.0233 (2)
O1	0.2321 (3)	0.7285 (2)	0.13758 (16)	0.0188 (5)
O2	0.3998 (3)	0.4777 (2)	0.10279 (16)	0.0154 (5)
N1	0.3105 (4)	0.2459 (3)	0.3171 (2)	0.0156 (6)
N2	0.4081 (4)	0.1541 (3)	0.2438 (2)	0.0200 (6)
N3	0.3234 (4)	0.0093 (3)	0.4248 (2)	0.0170 (6)
C1	−0.0559 (5)	0.5013 (4)	0.2716 (3)	0.0196 (7)
H1A	−0.1291	0.5928	0.2934	0.029*
H1B	−0.0926	0.4099	0.3329	0.029*
H1C	−0.0808	0.5014	0.1948	0.029*
C2	0.3814 (5)	0.5474 (4)	0.3718 (3)	0.0206 (7)
H2A	0.3203	0.6445	0.3888	0.031*
H2B	0.5127	0.5542	0.3327	0.031*
H2C	0.3791	0.4651	0.4465	0.031*
C3	0.4119 (5)	0.0140 (4)	0.3117 (3)	0.0203 (7)
H3A	0.4696	−0.0738	0.2852	0.024*
C4	0.2588 (5)	0.1574 (3)	0.4269 (2)	0.0158 (7)
C5	0.2958 (5)	−0.1263 (3)	0.5236 (2)	0.0220 (8)
H5A	0.2864	−0.1025	0.5989	0.033*
H5B	0.4033	−0.2079	0.5155	0.033*
H5C	0.1793	−0.1599	0.5231	0.033*
C6	0.7959 (5)	0.2468 (4)	0.1196 (3)	0.0234 (8)
H6A	0.7568	0.2827	0.1912	0.035*
H6B	0.9060	0.2915	0.0701	0.035*
H6C	0.8288	0.1351	0.1427	0.035*
C7	0.3661 (5)	0.2266 (4)	−0.0232 (3)	0.0218 (7)
H7A	0.2444	0.2463	0.0280	0.033*
H7B	0.4044	0.1162	−0.0117	0.033*
H7C	0.3538	0.2769	−0.1068	0.033*
C8	0.1025 (5)	0.8628 (3)	0.1446 (3)	0.0236 (8)
H8A	0.0946	0.8810	0.2218	0.035*
H8B	−0.0223	0.8510	0.1364	0.035*
H8C	0.1450	0.9496	0.0804	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01333 (13)	0.01317 (12)	0.01025 (11)	−0.00160 (9)	−0.00007 (8)	−0.00313 (8)
Sn2	0.01480 (13)	0.01053 (11)	0.01182 (11)	−0.00096 (9)	0.00021 (8)	−0.00231 (8)
S1	0.0276 (5)	0.0250 (4)	0.0145 (4)	−0.0043 (4)	0.0027 (3)	−0.0063 (3)
O1	0.0232 (14)	0.0111 (10)	0.0144 (10)	0.0027 (10)	0.0031 (9)	−0.0012 (8)
O2	0.0194 (13)	0.0125 (10)	0.0090 (9)	−0.0008 (9)	0.0043 (9)	−0.0016 (8)
N1	0.0175 (16)	0.0139 (13)	0.0134 (12)	−0.0016 (11)	−0.0005 (11)	−0.0031 (10)
N2	0.0265 (18)	0.0168 (14)	0.0144 (12)	−0.0033 (13)	0.0013 (12)	−0.0047 (11)
N3	0.0187 (16)	0.0154 (13)	0.0168 (12)	−0.0066 (12)	−0.0015 (11)	−0.0029 (10)
C1	0.0143 (19)	0.0224 (17)	0.0223 (16)	−0.0030 (14)	−0.0044 (14)	−0.0055 (13)
C2	0.024 (2)	0.0227 (17)	0.0196 (16)	−0.0058 (15)	−0.0079 (14)	−0.0071 (13)
C3	0.027 (2)	0.0149 (16)	0.0173 (15)	−0.0011 (15)	0.0006 (14)	−0.0065 (13)
C4	0.0167 (19)	0.0150 (15)	0.0151 (15)	−0.0033 (13)	−0.0060 (13)	−0.0004 (12)
C5	0.030 (2)	0.0157 (16)	0.0172 (15)	−0.0087 (15)	−0.0033 (14)	0.0029 (13)
C6	0.023 (2)	0.0249 (18)	0.0221 (17)	−0.0021 (15)	−0.0051 (15)	−0.0062 (14)
C7	0.018 (2)	0.0245 (17)	0.0253 (17)	−0.0083 (15)	−0.0032 (14)	−0.0073 (14)
C8	0.028 (2)	0.0155 (16)	0.0206 (16)	0.0016 (15)	0.0046 (14)	−0.0057 (13)

Geometric parameters (Å, º) top

Sn1—O2	2.0235 (19)	N3—C5	1.453 (4)
Sn1—C2	2.110 (3)	C1—H1A	0.9800
Sn1—C1	2.114 (3)	C1—H1B	0.9800
Sn1—O1	2.1637 (19)	C1—H1C	0.9800
Sn1—N1	2.239 (2)	C2—H2A	0.9800
Sn2—O2ⁱ	2.0717 (19)	C2—H2B	0.9800
Sn2—O2	2.1014 (19)	C2—H2C	0.9800
Sn2—C7	2.110 (3)	C3—H3A	0.9500
Sn2—C6	2.110 (3)	C5—H5A	0.9800
Sn2—O1ⁱ	2.202 (2)	C5—H5B	0.9800
Sn2—N2	2.757 (3)	C5—H5C	0.9800
S1—C4	1.702 (3)	C6—H6A	0.9800
O1—C8	1.410 (4)	C6—H6B	0.9800
O1—Sn2ⁱ	2.202 (2)	C6—H6C	0.9800
O2—Sn2ⁱ	2.0717 (19)	C7—H7A	0.9800
N1—C4	1.338 (4)	C7—H7B	0.9800
N1—N2	1.392 (3)	C7—H7C	0.9800
N2—C3	1.304 (4)	C8—H8A	0.9800
N3—C3	1.356 (4)	C8—H8B	0.9800
N3—C4	1.366 (4)	C8—H8C	0.9800

O2—Sn1—C2	113.32 (11)	Sn1—C1—H1B	109.5
O2—Sn1—C1	115.63 (10)	H1A—C1—H1B	109.5
C2—Sn1—C1	130.58 (13)	Sn1—C1—H1C	109.5
O2—Sn1—O1	73.45 (8)	H1A—C1—H1C	109.5
C2—Sn1—O1	92.65 (10)	H1B—C1—H1C	109.5
C1—Sn1—O1	94.71 (11)	Sn1—C2—H2A	109.5
O2—Sn1—N1	83.59 (8)	Sn1—C2—H2B	109.5
C2—Sn1—N1	96.97 (11)	H2A—C2—H2B	109.5
C1—Sn1—N1	94.75 (11)	Sn1—C2—H2C	109.5
O1—Sn1—N1	157.03 (8)	H2A—C2—H2C	109.5
O2ⁱ—Sn2—O2	74.62 (8)	H2B—C2—H2C	109.5
O2ⁱ—Sn2—C7	106.60 (11)	N2—C3—N3	111.7 (3)
O2—Sn2—C7	100.71 (11)	N2—C3—H3A	124.2
O2ⁱ—Sn2—C6	109.11 (11)	N3—C3—H3A	124.2
O2—Sn2—C6	99.99 (10)	N1—C4—N3	107.2 (2)
C7—Sn2—C6	142.30 (13)	N1—C4—S1	126.7 (2)
O2ⁱ—Sn2—O1ⁱ	71.73 (7)	N3—C4—S1	126.0 (2)
O2—Sn2—O1ⁱ	146.35 (8)	N3—C5—H5A	109.5
C7—Sn2—O1ⁱ	89.12 (11)	N3—C5—H5B	109.5
C6—Sn2—O1ⁱ	90.78 (11)	H5A—C5—H5B	109.5
O2ⁱ—Sn2—N2	148.29 (8)	N3—C5—H5C	109.5
O2—Sn2—N2	73.68 (7)	H5A—C5—H5C	109.5
C7—Sn2—N2	78.86 (10)	H5B—C5—H5C	109.5
C6—Sn2—N2	77.22 (11)	Sn2—C6—H6A	109.5
O1ⁱ—Sn2—N2	139.97 (7)	Sn2—C6—H6B	109.5
C8—O1—Sn1	128.80 (18)	H6A—C6—H6B	109.5
C8—O1—Sn2ⁱ	126.87 (17)	Sn2—C6—H6C	109.5
Sn1—O1—Sn2ⁱ	102.34 (8)	H6A—C6—H6C	109.5
Sn1—O2—Sn2ⁱ	112.30 (9)	H6B—C6—H6C	109.5
Sn1—O2—Sn2	142.18 (10)	Sn2—C7—H7A	109.5
Sn2ⁱ—O2—Sn2	105.38 (8)	Sn2—C7—H7B	109.5
C4—N1—N2	109.3 (2)	H7A—C7—H7B	109.5
C4—N1—Sn1	125.19 (19)	Sn2—C7—H7C	109.5
N2—N1—Sn1	125.43 (17)	H7A—C7—H7C	109.5
C3—N2—N1	105.4 (2)	H7B—C7—H7C	109.5
C3—N2—Sn2	139.7 (2)	O1—C8—H8A	109.5
N1—N2—Sn2	114.07 (17)	O1—C8—H8B	109.5
C3—N3—C4	106.5 (2)	H8A—C8—H8B	109.5
C3—N3—C5	127.0 (3)	O1—C8—H8C	109.5
C4—N3—C5	126.5 (3)	H8A—C8—H8C	109.5
Sn1—C1—H1A	109.5	H8B—C8—H8C	109.5

O2—Sn1—O1—C8	161.3 (3)	O2—Sn1—N1—N2	−7.7 (2)
C2—Sn1—O1—C8	−85.1 (3)	C2—Sn1—N1—N2	−120.5 (3)
C1—Sn1—O1—C8	46.0 (3)	C1—Sn1—N1—N2	107.6 (3)
N1—Sn1—O1—C8	160.0 (3)	O1—Sn1—N1—N2	−6.4 (4)
O2—Sn1—O1—Sn2ⁱ	−3.20 (8)	C4—N1—N2—C3	−0.1 (4)
C2—Sn1—O1—Sn2ⁱ	110.35 (12)	Sn1—N1—N2—C3	−176.4 (2)
C1—Sn1—O1—Sn2ⁱ	−118.56 (11)	C4—N1—N2—Sn2	−171.7 (2)
N1—Sn1—O1—Sn2ⁱ	−4.5 (3)	Sn1—N1—N2—Sn2	11.9 (3)
C2—Sn1—O2—Sn2ⁱ	−82.07 (13)	O2ⁱ—Sn2—N2—C3	−177.7 (3)
C1—Sn1—O2—Sn2ⁱ	90.87 (13)	O2—Sn2—N2—C3	−176.5 (4)
O1—Sn1—O2—Sn2ⁱ	3.60 (9)	C7—Sn2—N2—C3	78.7 (4)
N1—Sn1—O2—Sn2ⁱ	−176.92 (12)	C6—Sn2—N2—C3	−71.9 (4)
C2—Sn1—O2—Sn2	92.7 (2)	O1ⁱ—Sn2—N2—C3	3.7 (4)
C1—Sn1—O2—Sn2	−94.4 (2)	O2ⁱ—Sn2—N2—N1	−10.1 (3)
O1—Sn1—O2—Sn2	178.3 (2)	O2—Sn2—N2—N1	−8.9 (2)
N1—Sn1—O2—Sn2	−2.17 (19)	C7—Sn2—N2—N1	−113.7 (2)
O2ⁱ—Sn2—O2—Sn1	−175.0 (3)	C6—Sn2—N2—N1	95.6 (2)
C7—Sn2—O2—Sn1	80.6 (2)	O1ⁱ—Sn2—N2—N1	171.27 (18)
C6—Sn2—O2—Sn1	−67.7 (2)	N1—N2—C3—N3	−0.2 (4)
O1ⁱ—Sn2—O2—Sn1	−174.57 (14)	Sn2—N2—C3—N3	168.0 (2)
N2—Sn2—O2—Sn1	5.68 (17)	C4—N3—C3—N2	0.4 (4)
O2ⁱ—Sn2—O2—Sn2ⁱ	0.0	C5—N3—C3—N2	178.3 (3)
C7—Sn2—O2—Sn2ⁱ	−104.44 (12)	N2—N1—C4—N3	0.3 (4)
C6—Sn2—O2—Sn2ⁱ	107.23 (12)	Sn1—N1—C4—N3	176.7 (2)
O1ⁱ—Sn2—O2—Sn2ⁱ	0.4 (2)	N2—N1—C4—S1	178.7 (2)
N2—Sn2—O2—Sn2ⁱ	−179.36 (12)	Sn1—N1—C4—S1	−5.0 (4)
O2—Sn1—N1—C4	176.5 (3)	C3—N3—C4—N1	−0.5 (4)
C2—Sn1—N1—C4	63.7 (3)	C5—N3—C4—N1	−178.4 (3)
C1—Sn1—N1—C4	−68.2 (3)	C3—N3—C4—S1	−178.8 (3)
O1—Sn1—N1—C4	177.8 (2)	C5—N3—C4—S1	3.3 (5)

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Sn₄(CH₃)₈(C₃H₄N₃S)₂(CH₃O)₂O₂]
M_r	917.40
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.3693 (6), 9.3457 (8), 11.9930 (9)
α, β, γ (°)	71.681 (7), 76.780 (6), 77.118 (7)
V (Å³)	753.07 (11)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	3.45
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, 2010)
T_min, T_max	0.425, 0.546
No. of measured, independent and observed [I > 2σ(I)] reflections	5805, 3328, 2919
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.047, 0.98
No. of reflections	3328
No. of parameters	152
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.83, −0.77

Computer programs: CrysAlis PRO (Agilent Technologies, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

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

References

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