Bis(μ-2-methyl­quinolin-8-olato)-κ3N,O:O;κ3O:N,O-bis­[(methanol-κO)(nitrato-κ2O,O′)lead(II)]

Mohammadnezhad Sh., G.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536809003547

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page m259

doi:10.1107/S1600536809003547

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Bis(μ-2-methylquinolin-8-olato)-κ³N,O:O;κ³O:N,O-bis[(methanol-κO)(nitrato-κ²O,O′)lead(II)]

Gholamhossein Mohammadnezhad Sh.,^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 27 January 2009; accepted 29 January 2009; online 11 February 2009)

The molecule of the title compound, [Pb₂(C₁₀H₈NO)₂(NO₃)₂(CH₃OH)₂], lies about a centre of inversion. The Pb atom is chelated by nitrate and substituted quinolin-8-olate anions. The O atom of the quinolin-8-olate also bridges, to confer a six-coordinate status on the metal centre. When a longer Pb⋯O interaction is considered, the geometry approximates a Ψ-cube in which one of the sites is occupied by a stereochemically active lone pair.

Related literature

The 8-hydroxyquinolinate group engages in μ₃-bridging in dinitratohexa(quinolin-8-olato)tetralead(II); see: Zhang et al. (2008 ). It also exhibits this feature in the chain compound, bis(methanol)dinitratodi(quinolin-8-olato)dilead(II); see Shahverdizadeh et al. (2008 ). Both reports comment on lone-pair stereochemistry in this class of lead(II) compounds.

Experimental

Crystal data

[Pb₂(C₁₀H₈NO)₂(NO₃)₂(CH₄O)₂]
M_r = 918.83
Triclinic, $[P \overline 1]$
a = 8.2579 (1) Å
b = 8.8052 (1) Å
c = 9.6765 (1) Å
α = 103.976 (1)°
β = 98.262 (1)°
γ = 108.190 (1)°
V = 630.07 (1) Å³
Z = 1
Mo Kα radiation
μ = 13.41 mm⁻¹
T = 100 (2) K
0.20 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.175, T_max = 0.554 (expected range = 0.162–0.512)
5958 measured reflections
2872 independent reflections
2754 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.058
S = 1.08
2872 reflections
174 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.41 e Å⁻³
Δρ_min = −2.12 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); 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/S1600536809003547/tk2363sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809003547/tk2363Isup2.hkl

checkCIF report

Related literature top

The 8-hydroxyquinolinate group engages in µ₃-bridging in dinitratohexa(quinolin-8-olato)tetralead(II); see: Zhang et al. (2008). It also exhibits this feature in the chain compound, bis(methanol)dinitratodi(quinolin-8-olato)dilead(II); see Shahverdizadeh et al. (2008). Both reports comment on lone-pair stereochemistry in this class of lead(II) compounds.

Experimental top

Lead nitrate (0.33 g, 1 mmol) and 2-methyl-8-hydroxyquinoline (0.32 g, 2 mmol) were loaded into a convection tube; the tube was filled with dry methanol and kept at 333 K. Crystals were collected from the side arm after 3 d.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 Pb₂(NO₃)₂(CH₄O)₂(C₁₀H₈NO)₂; ellipsoids are drawn at the 70% probability level and H atoms of arbitrary radius. The unlabelled atoms are related by 1-x, 2-y, 1-z.
	Fig. 2. Detail of the environment of the Pb atom. Symmetry codes: (i) 1 - x, 2 - y, 1 - z; (ii) 1 - x, 1 - y, 1 - z.

Bis(µ-2-methylquinolin-8-olato)- κ³N,O:O;κ³O:N,O- bis[(methanol-κO)(nitrato-κ²O,O')lead(II)] top

Crystal data top

[Pb₂(C₁₀H₈NO)₂(NO₃)₂(CH₄O)₂]	Z = 1
M_r = 918.83	F(000) = 428
Triclinic, P1	D_x = 2.422 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2579 (1) Å	Cell parameters from 5067 reflections
b = 8.8052 (1) Å	θ = 2.2–28.3°
c = 9.6765 (1) Å	µ = 13.41 mm⁻¹
α = 103.976 (1)°	T = 100 K
β = 98.262 (1)°	Block, yellow
γ = 108.190 (1)°	0.20 × 0.15 × 0.05 mm
V = 630.07 (1) Å³

Data collection top

Bruker SMART APEX diffractometer	2872 independent reflections
Radiation source: fine-focus sealed tube	2754 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.175, T_max = 0.554	k = −11→11
5958 measured reflections	l = −12→12

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.058	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0341P)² + 1.3909P] where P = (F_o² + 2F_c²)/3
2872 reflections	(Δ/σ)_max = 0.001
174 parameters	Δρ_max = 1.41 e Å⁻³
1 restraint	Δρ_min = −2.12 e Å⁻³

Crystal data top

[Pb₂(C₁₀H₈NO)₂(NO₃)₂(CH₄O)₂]	γ = 108.190 (1)°
M_r = 918.83	V = 630.07 (1) Å³
Triclinic, P1	Z = 1
a = 8.2579 (1) Å	Mo Kα radiation
b = 8.8052 (1) Å	µ = 13.41 mm⁻¹
c = 9.6765 (1) Å	T = 100 K
α = 103.976 (1)°	0.20 × 0.15 × 0.05 mm
β = 98.262 (1)°

Data collection top

Bruker SMART APEX diffractometer	2872 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2754 reflections with I > 2σ(I)
T_min = 0.175, T_max = 0.554	R_int = 0.019
5958 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	1 restraint
wR(F²) = 0.058	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 1.41 e Å⁻³
2872 reflections	Δρ_min = −2.12 e Å⁻³
174 parameters

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

	x	y	z	U_iso*/U_eq
Pb1	0.403585 (18)	0.747859 (17)	0.434423 (15)	0.01020 (6)
O1	0.5672 (4)	0.9839 (4)	0.3886 (3)	0.0139 (6)
O2	0.7047 (5)	0.7066 (4)	0.4111 (4)	0.0202 (7)
O3	0.6609 (5)	0.6459 (5)	0.6104 (4)	0.0263 (8)
O4	0.8652 (5)	0.5918 (5)	0.5137 (4)	0.0261 (8)
O5	0.0903 (4)	0.7403 (4)	0.3446 (4)	0.0175 (6)
H5	0.006 (6)	0.691 (7)	0.376 (7)	0.028 (17)*
N1	0.3858 (5)	0.7002 (4)	0.1665 (4)	0.0114 (7)
N2	0.7441 (5)	0.6484 (5)	0.5124 (4)	0.0146 (7)
C1	0.6165 (6)	0.9696 (5)	0.2615 (5)	0.0123 (8)
C2	0.7547 (6)	1.0900 (6)	0.2411 (5)	0.0169 (9)
H2	0.8219	1.1885	0.3203	0.020*
C3	0.7985 (6)	1.0691 (6)	0.1028 (5)	0.0205 (9)
H3	0.8963	1.1529	0.0913	0.025*
C4	0.7024 (6)	0.9308 (6)	−0.0140 (5)	0.0199 (9)
H4	0.7315	0.9203	−0.1065	0.024*
C5	0.5592 (6)	0.8028 (5)	0.0032 (5)	0.0141 (8)
C6	0.5180 (5)	0.8209 (5)	0.1415 (4)	0.0115 (8)
C7	0.4520 (6)	0.6577 (6)	−0.1116 (5)	0.0167 (9)
H7	0.4731	0.6417	−0.2070	0.020*
C8	0.3161 (6)	0.5389 (6)	−0.0852 (5)	0.0165 (9)
H8	0.2419	0.4414	−0.1626	0.020*
C9	0.2879 (5)	0.5628 (5)	0.0573 (5)	0.0121 (8)
C10	0.1480 (5)	0.4306 (4)	0.0890 (5)	0.0160 (9)
H10A	0.2007	0.3646	0.1358	0.024*
H10B	0.0632	0.3567	−0.0028	0.024*
H10C	0.0879	0.4834	0.1549	0.024*
C11	0.0687 (6)	0.8890 (4)	0.3246 (5)	0.0257 (11)
H11A	0.0928	0.9717	0.4205	0.039*
H11B	−0.0520	0.8616	0.2712	0.039*
H11C	0.1504	0.9358	0.2684	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb1	0.01050 (9)	0.00980 (9)	0.01087 (9)	0.00331 (6)	0.00258 (6)	0.00458 (6)
O1	0.0147 (15)	0.0116 (13)	0.0134 (14)	0.0013 (12)	0.0045 (12)	0.0043 (11)
O2	0.0235 (18)	0.0268 (17)	0.0212 (16)	0.0148 (14)	0.0101 (14)	0.0161 (14)
O3	0.0270 (19)	0.046 (2)	0.0163 (16)	0.0181 (17)	0.0125 (14)	0.0177 (16)
O4	0.0162 (17)	0.0333 (19)	0.039 (2)	0.0136 (15)	0.0108 (15)	0.0205 (17)
O5	0.0129 (16)	0.0205 (16)	0.0227 (16)	0.0073 (13)	0.0072 (13)	0.0098 (13)
N1	0.0117 (17)	0.0121 (16)	0.0120 (16)	0.0041 (14)	0.0028 (13)	0.0067 (13)
N2	0.0126 (18)	0.0164 (17)	0.0159 (17)	0.0051 (14)	0.0036 (14)	0.0068 (14)
C1	0.014 (2)	0.0129 (18)	0.0128 (19)	0.0072 (16)	0.0030 (16)	0.0055 (16)
C2	0.017 (2)	0.015 (2)	0.017 (2)	0.0048 (17)	0.0033 (17)	0.0049 (17)
C3	0.018 (2)	0.019 (2)	0.027 (2)	0.0039 (18)	0.0113 (19)	0.0115 (19)
C4	0.021 (2)	0.022 (2)	0.022 (2)	0.0080 (19)	0.0124 (19)	0.0110 (19)
C5	0.015 (2)	0.017 (2)	0.0138 (19)	0.0064 (17)	0.0063 (16)	0.0096 (17)
C6	0.0095 (19)	0.0148 (19)	0.0134 (19)	0.0071 (16)	0.0022 (15)	0.0067 (16)
C7	0.018 (2)	0.021 (2)	0.014 (2)	0.0101 (18)	0.0053 (17)	0.0049 (17)
C8	0.014 (2)	0.017 (2)	0.017 (2)	0.0061 (17)	0.0020 (16)	0.0030 (17)
C9	0.0088 (19)	0.0137 (19)	0.0140 (19)	0.0047 (16)	0.0011 (15)	0.0045 (16)
C10	0.011 (2)	0.0125 (19)	0.020 (2)	−0.0014 (16)	0.0022 (16)	0.0038 (16)
C11	0.022 (3)	0.024 (2)	0.036 (3)	0.010 (2)	0.008 (2)	0.014 (2)

Geometric parameters (Å, º) top

Pb1—O1	2.281 (3)	C2—C3	1.421 (6)
Pb1—O1ⁱ	2.478 (3)	C2—H2	0.9500
Pb1—N1	2.499 (3)	C3—C4	1.365 (7)
Pb1—O5	2.583 (3)	C3—H3	0.9500
Pb1—O2	2.655 (3)	C4—C5	1.418 (6)
Pb1—O3	3.019 (4)	C4—H4	0.9500
Pb1—O3ⁱⁱ	3.248 (4)	C5—C7	1.406 (6)
Pb1—O4ⁱⁱ	3.320 (4)	C5—C6	1.412 (6)
O1—C1	1.341 (5)	C7—C8	1.378 (6)
O1—Pb1ⁱ	2.478 (3)	C7—H7	0.9500
O2—N2	1.259 (5)	C8—C9	1.408 (6)
O3—N2	1.248 (5)	C8—H8	0.9500
O4—N2	1.248 (5)	C9—C10	1.490 (5)
O5—C11	1.430 (5)	C10—H10A	0.9800
O5—H5	0.838 (10)	C10—H10B	0.9800
N1—C9	1.326 (5)	C10—H10C	0.9800
N1—C6	1.362 (5)	C11—H11A	0.9800
C1—C2	1.369 (6)	C11—H11B	0.9800
C1—C6	1.433 (6)	C11—H11C	0.9800

O1—Pb1—O1ⁱ	64.88 (12)	O4—N2—O2	119.8 (4)
O1—Pb1—N1	68.38 (11)	O1—C1—C2	123.2 (4)
O1ⁱ—Pb1—N1	124.94 (11)	O1—C1—C6	117.8 (4)
O1—Pb1—O5	100.85 (11)	C2—C1—C6	119.0 (4)
O1ⁱ—Pb1—O5	82.53 (10)	C1—C2—C3	120.6 (4)
N1—Pb1—O5	79.21 (11)	C1—C2—H2	119.7
O1—Pb1—O2	75.46 (11)	C3—C2—H2	119.7
O1ⁱ—Pb1—O2	114.95 (11)	C4—C3—C2	121.2 (4)
N1—Pb1—O2	78.25 (11)	C4—C3—H3	119.4
O5—Pb1—O2	156.87 (11)	C2—C3—H3	119.4
O1—Pb1—O3	105.98 (11)	C3—C4—C5	119.8 (4)
O1ⁱ—Pb1—O3	100.58 (10)	C3—C4—H4	120.1
N1—Pb1—O3	119.16 (10)	C5—C4—H4	120.1
O5—Pb1—O3	151.65 (10)	C7—C5—C6	117.2 (4)
O2—Pb1—O3	44.42 (9)	C7—C5—C4	123.5 (4)
O1—Pb1—O3ⁱⁱ	144.45 (10)	C6—C5—C4	119.3 (4)
O1ⁱ—Pb1—O3ⁱⁱ	144.84 (9)	N1—C6—C5	122.2 (4)
N1—Pb1—O3ⁱⁱ	89.96 (10)	N1—C6—C1	117.7 (4)
O5—Pb1—O3ⁱⁱ	102.30 (10)	C5—C6—C1	120.2 (4)
O2—Pb1—O3ⁱⁱ	72.63 (10)	C8—C7—C5	119.8 (4)
O3—Pb1—O3ⁱⁱ	59.42 (12)	C8—C7—H7	120.1
O1—Pb1—O4ⁱⁱ	175.03 (10)	C5—C7—H7	120.1
O1ⁱ—Pb1—O4ⁱⁱ	114.40 (10)	C7—C8—C9	119.6 (4)
N1—Pb1—O4ⁱⁱ	109.62 (11)	C7—C8—H8	120.2
O5—Pb1—O4ⁱⁱ	74.21 (9)	C9—C8—H8	120.2
O2—Pb1—O4ⁱⁱ	108.83 (9)	N1—C9—C8	121.5 (4)
O3—Pb1—O4ⁱⁱ	78.99 (10)	N1—C9—C10	118.5 (4)
O3ⁱⁱ—Pb1—O4ⁱⁱ	38.47 (9)	C8—C9—C10	120.0 (4)
C1—O1—Pb1	119.2 (2)	C9—C10—H10A	109.5
C1—O1—Pb1ⁱ	124.9 (2)	C9—C10—H10B	109.5
Pb1—O1—Pb1ⁱ	115.12 (12)	H10A—C10—H10B	109.5
N2—O2—Pb1	106.1 (2)	C9—C10—H10C	109.5
N2—O3—Pb1	88.6 (2)	H10A—C10—H10C	109.5
C11—O5—Pb1	118.7 (2)	H10B—C10—H10C	109.5
C11—O5—H5	108 (4)	O5—C11—H11A	109.5
Pb1—O5—H5	122 (4)	O5—C11—H11B	109.5
C9—N1—C6	119.7 (4)	H11A—C11—H11B	109.5
C9—N1—Pb1	127.4 (3)	O5—C11—H11C	109.5
C6—N1—Pb1	111.6 (3)	H11A—C11—H11C	109.5
O3—N2—O4	120.2 (4)	H11B—C11—H11C	109.5
O3—N2—O2	119.9 (4)

O1ⁱ—Pb1—O1—C1	−170.3 (4)	O1—Pb1—N1—C6	17.3 (3)
N1—Pb1—O1—C1	−20.3 (3)	O1ⁱ—Pb1—N1—C6	50.8 (3)
O5—Pb1—O1—C1	−93.9 (3)	O5—Pb1—N1—C6	123.7 (3)
O2—Pb1—O1—C1	62.6 (3)	O2—Pb1—N1—C6	−61.5 (3)
O3—Pb1—O1—C1	95.3 (3)	O3—Pb1—N1—C6	−79.4 (3)
O3ⁱⁱ—Pb1—O1—C1	36.0 (4)	O3ⁱⁱ—Pb1—N1—C6	−133.8 (3)
O4ⁱⁱ—Pb1—O1—C1	−87.4 (12)	O4ⁱⁱ—Pb1—N1—C6	−167.5 (3)
O1ⁱ—Pb1—O1—Pb1ⁱ	0.0	Pb1—O3—N2—O4	−170.3 (4)
N1—Pb1—O1—Pb1ⁱ	150.03 (17)	Pb1—O3—N2—O2	9.0 (4)
O5—Pb1—O1—Pb1ⁱ	76.34 (14)	Pb1—O2—N2—O3	−10.7 (5)
O2—Pb1—O1—Pb1ⁱ	−127.07 (15)	Pb1—O2—N2—O4	168.6 (3)
O3—Pb1—O1—Pb1ⁱ	−94.40 (14)	Pb1—O1—C1—C2	−159.2 (3)
O3ⁱⁱ—Pb1—O1—Pb1ⁱ	−153.76 (12)	Pb1ⁱ—O1—C1—C2	31.5 (6)
O4ⁱⁱ—Pb1—O1—Pb1ⁱ	82.9 (12)	Pb1—O1—C1—C6	21.2 (5)
O1—Pb1—O2—N2	137.6 (3)	Pb1ⁱ—O1—C1—C6	−148.1 (3)
O1ⁱ—Pb1—O2—N2	84.7 (3)	O1—C1—C2—C3	−178.8 (4)
N1—Pb1—O2—N2	−152.0 (3)	C6—C1—C2—C3	0.8 (7)
O5—Pb1—O2—N2	−138.9 (3)	C1—C2—C3—C4	1.4 (7)
O3—Pb1—O2—N2	5.4 (2)	C2—C3—C4—C5	−1.8 (7)
O3ⁱⁱ—Pb1—O2—N2	−58.3 (3)	C3—C4—C5—C7	179.0 (5)
O4ⁱⁱ—Pb1—O2—N2	−45.1 (3)	C3—C4—C5—C6	0.1 (7)
O1—Pb1—O3—N2	−53.6 (3)	C9—N1—C6—C5	−2.1 (6)
O1ⁱ—Pb1—O3—N2	−120.3 (3)	Pb1—N1—C6—C5	166.0 (3)
N1—Pb1—O3—N2	20.2 (3)	C9—N1—C6—C1	178.0 (4)
O5—Pb1—O3—N2	145.9 (3)	Pb1—N1—C6—C1	−13.9 (4)
O2—Pb1—O3—N2	−5.3 (2)	C7—C5—C6—N1	3.2 (6)
O3ⁱⁱ—Pb1—O3—N2	90.9 (3)	C4—C5—C6—N1	−177.8 (4)
O4ⁱⁱ—Pb1—O3—N2	126.7 (3)	C7—C5—C6—C1	−176.9 (4)
O1—Pb1—O5—C11	−16.8 (3)	C4—C5—C6—C1	2.0 (6)
O1ⁱ—Pb1—O5—C11	45.7 (3)	O1—C1—C6—N1	−3.0 (6)
N1—Pb1—O5—C11	−82.1 (3)	C2—C1—C6—N1	177.4 (4)
O2—Pb1—O5—C11	−95.2 (4)	O1—C1—C6—C5	177.1 (4)
O3—Pb1—O5—C11	144.2 (3)	C2—C1—C6—C5	−2.5 (6)
O3ⁱⁱ—Pb1—O5—C11	−169.7 (3)	C6—C5—C7—C8	−1.5 (6)
O4ⁱⁱ—Pb1—O5—C11	163.8 (3)	C4—C5—C7—C8	179.6 (4)
O1—Pb1—N1—C9	−175.7 (4)	C5—C7—C8—C9	−1.0 (7)
O1ⁱ—Pb1—N1—C9	−142.2 (3)	C6—N1—C9—C8	−0.7 (6)
O5—Pb1—N1—C9	−69.4 (3)	Pb1—N1—C9—C8	−166.7 (3)
O2—Pb1—N1—C9	105.4 (4)	C6—N1—C9—C10	178.1 (4)
O3—Pb1—N1—C9	87.5 (4)	Pb1—N1—C9—C10	12.1 (5)
O3ⁱⁱ—Pb1—N1—C9	33.2 (4)	C7—C8—C9—N1	2.3 (7)
O4ⁱⁱ—Pb1—N1—C9	−0.6 (4)	C7—C8—C9—C10	−176.5 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O4ⁱⁱⁱ	0.84 (1)	2.06 (2)	2.869 (5)	161 (6)

Symmetry code: (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Pb₂(C₁₀H₈NO)₂(NO₃)₂(CH₄O)₂]
M_r	918.83
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.2579 (1), 8.8052 (1), 9.6765 (1)
α, β, γ (°)	103.976 (1), 98.262 (1), 108.190 (1)
V (Å³)	630.07 (1)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	13.41
Crystal size (mm)	0.20 × 0.15 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.175, 0.554
No. of measured, independent and observed [I > 2σ(I)] reflections	5958, 2872, 2754
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.058, 1.08
No. of reflections	2872
No. of parameters	174
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)	1.41, −2.12

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

Acknowledgements

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

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Shahverdizadeh, G. H., Soudi, A. A., Morsali, A. & Retailleau, P. (2008). Inorg. Chim. Acta, 361, 1875–1884. Web of Science CSD CrossRef CAS 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
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar
Zhang, W.-Z., Wei, D.-Z., Che, X.-F., Gao, E.-J., Wang, K.-H., Yin, H.-X. & Gu, X.-G. (2008). Chin. J. Struct. Chem. 27, 287–292. Web of Science CrossRef CAS Google Scholar

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