catena-Poly[[(1,10-phenanthroline-κ2N,N′)lead(II)]-μ-azido-κ2N1:N3-μ-nitrito-κ3O,O′:O′-[(1,10-phenanthroline-κ2N,N′)lead(II)]-di-μ-azido-κ4N1:N1]

Mohammadnezhad, G.; Ghanbarpour, A.R.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536810022907

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page m821

doi:10.1107/S1600536810022907

Open

access

catena-Poly[[(1,10-phenanthroline-κ²N,N′)lead(II)]-μ-azido-κ²N¹:N³-μ-nitrito-κ³O,O′:O′-[(1,10-phenanthroline-κ²N,N′)lead(II)]-di-μ-azido-κ⁴N¹:N¹]

Gholamhossein Mohammadnezhad,^a Ali Reza Ghanbarpour,^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 31 May 2010; accepted 14 June 2010; online 18 June 2010)

The title coordination polymer, [Pb₂(N₃)₃(NO₂)(C₁₂H₈N₂)₂]_n, has as the repeat unit a centrosymmetric dinuclear molecule having azide and nitrite groups that bridge adjacent heterocycle-coordinated metal centers. One of the azide group uses its terminal ends to bridge whereas the nitrite group chelates to one metal atom and uses one of its O atoms to bridge. The azide and nitrite groups are disordered with respect to each other in a 1:1 ratio. Adjacent dinuclear molecules are further bridged by the other two azide groups, generating a linear chain motif parallel to [010]. Half of the Pb atoms show a Ψ-dodecahedral coordination and the other half show a Ψ-pentagonal-bipyramidal coordination.

Related literature

For the crystal structure of a related lead azide complex, see: Marandi et al. (2007 ).

Experimental

Crystal data

[Pb₂(N₃)₃(NO₂)(C₁₂H₈N₂)₂]
M_r = 946.89
Triclinic, $[P \overline 1]$
a = 7.6860 (5) Å
b = 9.2056 (6) Å
c = 9.9080 (7) Å
α = 90.541 (1)°
β = 109.665 (1)°
γ = 104.626 (1)°
V = 635.32 (7) Å³
Z = 1
Mo Kα radiation
μ = 13.29 mm⁻¹
T = 100 K
0.30 × 0.30 × 0.30 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.040, T_max = 0.109
6004 measured reflections
2888 independent reflections
2716 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.071
S = 1.03
2888 reflections
193 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 2.17 e Å⁻³
Δρ_min = −1.97 e Å⁻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: 10.1107/S1600536810022907/xu2775sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022907/xu2775Isup2.hkl

checkCIF report

Comment top

There are a number of 1,10-phenanthroline-chelated lead(II) compounds having inorganic anions (having only few atoms) as counterions whose crystal structures have been reported. For some, two counterions exist in the crystal structure that originally came from the reactants used in the synthesis.

The azide derivative is a polymeric dinuclear chain compound in which the lead atoms show PbN₈ and PbN₆O₂ dodecahedral coordination. In lead azide nicotinate, the azide unit engages in µ₃ bridging (Marandi et al., 2007). In Pb₂(N₃)₃(NO₂)(C₁₂H₈NO)₂(Scheme I, Fig. 1), the azide groups bridge adjacent heterocycle-coordinated metal centers through one nitrogen atom and the third bridging through two nitrogen atoms. The nitrite group chelates to one metal atom and uses one oxygen atom to bind to the inversion-related lead atom. The bridging interactions lead to the formation of a linear chain motif. One of the azide groups that uses its terminal nitrogen atoms to bridge is disordered with respect to the nitrite group in a 1:1 ratio. The disorder gives rise to a Ψ-dodecahedral geometry for 50% of the lead atoms and a Ψ-pentagonal bipyramidal geometry for the other 50% of the lead atoms.

Related literature top

For the crystal structure of a related lead azide complex, see: Marandi et al. (2007).

Experimental top

1,10-Phenanthroline (0.36 g, 2 mmol) and sodium azide (0.13 g, 1 mmol) were placed in one arm of a convection tube, and lead(II) nitrate (0.33 g, 1 mmol) and sodium nitrite (0.07 g, 1 mmol) in the other. Methanol was then added to fill both arms and the tube was sealed. The ligand-containing arm was immersed in an oil bath at 333 K, whereas the other was left at ambient temperature. After 1 day, crystals deposited in the arm that was kept at ambient temperature.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 Pb₂(N₃)₃(NO₂)(C₁₂H₈NO)₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. Symmetry code: i = 1 - x, 1 - y, 1 - z.

catena-Poly[[(1,10-phenanthroline-κN,N')lead(II)]-µ- azido-κ²N¹:N³-µ-nitrito- κ³O,O':O'-[(1,10-phenanthroline- κN,N')lead(II)]-di-µ-azido-κ⁴N¹:N¹] top

Crystal data top

[Pb₂(N₃)₃(NO₂)(C₁₂H₈N₂)₂]	Z = 1
M_r = 946.89	F(000) = 438
Triclinic, P1	D_x = 2.475 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6860 (5) Å	Cell parameters from 4831 reflections
b = 9.2056 (6) Å	θ = 2.3–28.3°
c = 9.9080 (7) Å	µ = 13.29 mm⁻¹
α = 90.541 (1)°	T = 100 K
β = 109.665 (1)°	Irregular, yellow
γ = 104.626 (1)°	0.30 × 0.30 × 0.30 mm
V = 635.32 (7) Å³

Data collection top

Bruker SMART APEX diffractometer	2888 independent reflections
Radiation source: fine-focus sealed tube	2716 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.040, T_max = 0.109	k = −11→11
6004 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.071	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0348P)² + 1.3333P] where P = (F_o² + 2F_c²)/3
2888 reflections	(Δ/σ)_max = 0.001
193 parameters	Δρ_max = 2.17 e Å⁻³
12 restraints	Δρ_min = −1.97 e Å⁻³

Crystal data top

[Pb₂(N₃)₃(NO₂)(C₁₂H₈N₂)₂]	γ = 104.626 (1)°
M_r = 946.89	V = 635.32 (7) Å³
Triclinic, P1	Z = 1
a = 7.6860 (5) Å	Mo Kα radiation
b = 9.2056 (6) Å	µ = 13.29 mm⁻¹
c = 9.9080 (7) Å	T = 100 K
α = 90.541 (1)°	0.30 × 0.30 × 0.30 mm
β = 109.665 (1)°

Data collection top

Bruker SMART APEX diffractometer	2888 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2716 reflections with I > 2σ(I)
T_min = 0.040, T_max = 0.109	R_int = 0.033
6004 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	12 restraints
wR(F²) = 0.071	H-atom parameters constrained
S = 1.03	Δρ_max = 2.17 e Å⁻³
2888 reflections	Δρ_min = −1.97 e Å⁻³
193 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Pb1	0.56829 (3)	0.79283 (2)	0.561361 (19)	0.00881 (8)
O1	0.7795 (7)	0.6258 (5)	0.7489 (5)	0.0169 (9)	0.50
O2	0.5962 (13)	0.4948 (9)	0.5579 (9)	0.0197 (14)	0.50
N1	0.7795 (7)	0.6258 (5)	0.7489 (5)	0.0169 (9)	0.50
N2	0.7445 (16)	0.3876 (12)	0.6296 (11)	0.0197 (14)	0.50
N3	0.7470 (8)	0.5047 (5)	0.6855 (5)	0.0156 (10)
N4	0.3085 (7)	0.9214 (6)	0.5147 (5)	0.0168 (10)
N5	0.1522 (7)	0.8609 (5)	0.5166 (5)	0.0136 (10)
N6	−0.0006 (8)	0.8055 (6)	0.5194 (6)	0.0260 (12)
N7	0.4053 (6)	0.6818 (5)	0.7324 (5)	0.0090 (9)
N8	0.6931 (7)	0.9476 (5)	0.8019 (5)	0.0085 (9)
C1	0.2609 (8)	0.5559 (6)	0.6968 (6)	0.0124 (11)
H1	0.2033	0.5142	0.5988	0.015*
C2	0.1915 (8)	0.4829 (6)	0.7996 (7)	0.0148 (11)
H2	0.0900	0.3924	0.7718	0.018*
C3	0.2717 (8)	0.5438 (6)	0.9397 (6)	0.0138 (11)
H3	0.2254	0.4958	1.0101	0.017*
C4	0.4224 (8)	0.6771 (6)	0.9804 (6)	0.0106 (10)
C5	0.4849 (8)	0.7444 (6)	0.8717 (6)	0.0084 (10)
C6	0.5120 (8)	0.7478 (6)	1.1264 (6)	0.0131 (11)
H6	0.4726	0.7008	1.2002	0.016*
C7	0.6505 (8)	0.8794 (7)	1.1603 (6)	0.0132 (11)
H7	0.7065	0.9244	1.2572	0.016*
C8	0.7146 (7)	0.9524 (6)	1.0510 (6)	0.0080 (10)
C9	0.6343 (7)	0.8846 (6)	0.9074 (6)	0.0081 (10)
C10	0.8545 (8)	1.0937 (6)	1.0810 (6)	0.0110 (11)
H10	0.9108	1.1433	1.1762	0.013*
C11	0.9080 (8)	1.1579 (6)	0.9729 (6)	0.0115 (11)
H11	1.0002	1.2532	0.9911	0.014*
C12	0.8231 (8)	1.0797 (6)	0.8329 (6)	0.0093 (10)
H12	0.8615	1.1243	0.7577	0.011*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb1	0.01002 (12)	0.00884 (11)	0.00691 (11)	0.00024 (7)	0.00383 (8)	−0.00010 (7)
O1	0.017 (2)	0.016 (2)	0.017 (2)	0.0021 (18)	0.0072 (19)	−0.0037 (17)
O2	0.024 (4)	0.018 (3)	0.017 (3)	0.004 (3)	0.009 (3)	−0.004 (2)
N1	0.017 (2)	0.016 (2)	0.017 (2)	0.0021 (18)	0.0072 (19)	−0.0037 (17)
N2	0.024 (4)	0.018 (3)	0.017 (3)	0.004 (3)	0.009 (3)	−0.004 (2)
N3	0.021 (3)	0.014 (2)	0.012 (2)	0.005 (2)	0.006 (2)	−0.0002 (18)
N4	0.011 (3)	0.025 (3)	0.017 (3)	0.007 (2)	0.006 (2)	0.008 (2)
N5	0.015 (3)	0.017 (2)	0.010 (2)	0.006 (2)	0.0042 (19)	0.0014 (18)
N6	0.017 (3)	0.027 (3)	0.031 (3)	0.002 (2)	0.007 (2)	0.004 (2)
N7	0.006 (2)	0.010 (2)	0.011 (2)	0.0017 (17)	0.0026 (18)	0.0018 (17)
N8	0.009 (2)	0.008 (2)	0.007 (2)	0.0025 (17)	0.0007 (18)	−0.0018 (16)
C1	0.008 (3)	0.012 (3)	0.014 (3)	−0.001 (2)	0.003 (2)	−0.002 (2)
C2	0.007 (3)	0.012 (3)	0.023 (3)	−0.002 (2)	0.006 (2)	0.002 (2)
C3	0.010 (3)	0.013 (3)	0.022 (3)	0.003 (2)	0.010 (2)	0.004 (2)
C4	0.010 (3)	0.012 (3)	0.013 (3)	0.006 (2)	0.005 (2)	0.002 (2)
C5	0.008 (3)	0.010 (2)	0.007 (2)	0.004 (2)	0.003 (2)	0.0022 (19)
C6	0.016 (3)	0.017 (3)	0.010 (3)	0.004 (2)	0.008 (2)	0.003 (2)
C7	0.014 (3)	0.020 (3)	0.008 (3)	0.009 (2)	0.004 (2)	0.001 (2)
C8	0.003 (2)	0.011 (2)	0.010 (3)	0.0033 (19)	0.002 (2)	−0.0006 (19)
C9	0.005 (3)	0.010 (2)	0.010 (3)	0.0045 (19)	0.002 (2)	−0.0016 (19)
C10	0.007 (3)	0.014 (3)	0.011 (3)	0.005 (2)	0.001 (2)	−0.004 (2)
C11	0.007 (3)	0.008 (2)	0.016 (3)	0.0001 (19)	0.002 (2)	−0.002 (2)
C12	0.006 (3)	0.009 (2)	0.013 (3)	0.0025 (19)	0.004 (2)	0.0006 (19)

Geometric parameters (Å, º) top

Pb1—N4	2.487 (5)	C1—H1	0.9500
Pb1—N7	2.510 (4)	C2—C3	1.363 (8)
Pb1—N8	2.517 (4)	C2—H2	0.9500
Pb1—N2ⁱ	2.642 (11)	C3—C4	1.403 (8)
Pb1—O2ⁱ	2.693 (8)	C3—H3	0.9500
Pb1—N4ⁱⁱ	2.764 (5)	C4—C5	1.410 (8)
O1—N3	1.200 (6)	C4—C6	1.441 (8)
O2—N3	1.382 (10)	C5—C9	1.442 (7)
O2—Pb1ⁱ	2.693 (8)	C6—C7	1.347 (8)
N2—N3	1.200 (11)	C6—H6	0.9500
N2—Pb1ⁱ	2.642 (11)	C7—C8	1.440 (8)
N4—N5	1.196 (7)	C7—H7	0.9500
N4—Pb1ⁱⁱ	2.764 (5)	C8—C9	1.412 (7)
N5—N6	1.166 (7)	C8—C10	1.417 (7)
N7—C1	1.334 (7)	C10—C11	1.360 (8)
N7—C5	1.360 (7)	C10—H10	0.9500
N8—C12	1.321 (7)	C11—C12	1.416 (7)
N8—C9	1.353 (7)	C11—H11	0.9500
C1—C2	1.404 (8)	C12—H12	0.9500

N4—Pb1—N7	78.10 (15)	C3—C2—C1	119.1 (5)
N4—Pb1—N8	82.36 (16)	C3—C2—H2	120.4
N7—Pb1—N8	66.32 (15)	C1—C2—H2	120.4
N4—Pb1—N2ⁱ	72.7 (3)	C2—C3—C4	120.3 (5)
N7—Pb1—N2ⁱ	81.9 (3)	C2—C3—H3	119.9
N8—Pb1—N2ⁱ	143.0 (2)	C4—C3—H3	119.9
N4—Pb1—O2ⁱ	107.5 (2)	C3—C4—C5	117.6 (5)
N7—Pb1—O2ⁱ	78.2 (2)	C3—C4—C6	123.0 (5)
N8—Pb1—O2ⁱ	140.5 (2)	C5—C4—C6	119.4 (5)
N2ⁱ—Pb1—O2ⁱ	36.6 (3)	N7—C5—C4	121.6 (5)
N4—Pb1—N4ⁱⁱ	70.67 (18)	N7—C5—C9	118.7 (5)
N7—Pb1—N4ⁱⁱ	135.88 (14)	C4—C5—C9	119.6 (5)
N8—Pb1—N4ⁱⁱ	79.09 (15)	C7—C6—C4	121.3 (5)
N2ⁱ—Pb1—N4ⁱⁱ	116.0 (3)	C7—C6—H6	119.4
O2ⁱ—Pb1—N4ⁱⁱ	140.4 (2)	C4—C6—H6	119.4
N3—O2—Pb1ⁱ	111.5 (5)	C6—C7—C8	120.5 (5)
N3—N2—Pb1ⁱ	123.2 (7)	C6—C7—H7	119.7
O1—N3—N2	170.0 (8)	C8—C7—H7	119.7
O1—N3—O2	107.1 (5)	C9—C8—C10	117.7 (5)
N2—N3—O2	80.7 (7)	C9—C8—C7	119.9 (5)
N5—N4—Pb1	123.2 (4)	C10—C8—C7	122.4 (5)
N5—N4—Pb1ⁱⁱ	127.3 (4)	N8—C9—C8	121.9 (5)
Pb1—N4—Pb1ⁱⁱ	109.33 (18)	N8—C9—C5	118.9 (5)
N6—N5—N4	178.2 (6)	C8—C9—C5	119.2 (5)
C1—N7—C5	119.3 (5)	C11—C10—C8	119.7 (5)
C1—N7—Pb1	123.0 (4)	C11—C10—H10	120.2
C5—N7—Pb1	117.2 (3)	C8—C10—H10	120.2
C12—N8—C9	119.0 (4)	C10—C11—C12	118.6 (5)
C12—N8—Pb1	123.5 (3)	C10—C11—H11	120.7
C9—N8—Pb1	117.2 (3)	C12—C11—H11	120.7
N7—C1—C2	122.0 (5)	N8—C12—C11	123.0 (5)
N7—C1—H1	119.0	N8—C12—H12	118.5
C2—C1—H1	119.0	C11—C12—H12	118.5

Pb1ⁱ—N2—N3—O1	−169 (4)	N7—C1—C2—C3	1.1 (9)
Pb1ⁱ—N2—N3—O2	−27.1 (7)	C1—C2—C3—C4	−0.4 (8)
Pb1ⁱ—O2—N3—O1	−162.7 (4)	C2—C3—C4—C5	0.4 (8)
Pb1ⁱ—O2—N3—N2	23.7 (7)	C2—C3—C4—C6	179.4 (5)
N7—Pb1—N4—N5	−36.2 (4)	C1—N7—C5—C4	1.9 (8)
N8—Pb1—N4—N5	−103.5 (5)	Pb1—N7—C5—C4	−170.4 (4)
N2ⁱ—Pb1—N4—N5	48.8 (5)	C1—N7—C5—C9	−176.9 (5)
O2ⁱ—Pb1—N4—N5	37.2 (5)	Pb1—N7—C5—C9	10.8 (6)
N4ⁱⁱ—Pb1—N4—N5	175.4 (6)	C3—C4—C5—N7	−1.2 (8)
N7—Pb1—N4—Pb1ⁱⁱ	148.4 (2)	C6—C4—C5—N7	179.8 (5)
N8—Pb1—N4—Pb1ⁱⁱ	81.06 (19)	C3—C4—C5—C9	177.6 (5)
N2ⁱ—Pb1—N4—Pb1ⁱⁱ	−126.5 (3)	C6—C4—C5—C9	−1.4 (8)
O2ⁱ—Pb1—N4—Pb1ⁱⁱ	−138.2 (2)	C3—C4—C6—C7	−177.0 (6)
N4ⁱⁱ—Pb1—N4—Pb1ⁱⁱ	0.0	C5—C4—C6—C7	2.0 (8)
N4—Pb1—N7—C1	90.6 (4)	C4—C6—C7—C8	−0.7 (8)
N8—Pb1—N7—C1	177.4 (5)	C6—C7—C8—C9	−1.2 (8)
N2ⁱ—Pb1—N7—C1	16.7 (5)	C6—C7—C8—C10	177.5 (5)
O2ⁱ—Pb1—N7—C1	−20.3 (4)	C12—N8—C9—C8	−3.1 (7)
N4ⁱⁱ—Pb1—N7—C1	135.9 (4)	Pb1—N8—C9—C8	171.4 (4)
N4—Pb1—N7—C5	−97.4 (4)	C12—N8—C9—C5	176.7 (5)
N8—Pb1—N7—C5	−10.6 (3)	Pb1—N8—C9—C5	−8.8 (6)
N2ⁱ—Pb1—N7—C5	−171.3 (4)	C10—C8—C9—N8	2.7 (7)
O2ⁱ—Pb1—N7—C5	151.7 (4)	C7—C8—C9—N8	−178.6 (5)
N4ⁱⁱ—Pb1—N7—C5	−52.1 (4)	C10—C8—C9—C5	−177.0 (5)
N4—Pb1—N8—C12	−95.5 (4)	C7—C8—C9—C5	1.7 (7)
N7—Pb1—N8—C12	−175.8 (4)	N7—C5—C9—N8	−1.3 (7)
N2ⁱ—Pb1—N8—C12	−142.9 (5)	C4—C5—C9—N8	179.9 (5)
O2ⁱ—Pb1—N8—C12	156.2 (4)	N7—C5—C9—C8	178.4 (5)
N4ⁱⁱ—Pb1—N8—C12	−23.8 (4)	C4—C5—C9—C8	−0.4 (7)
N4—Pb1—N8—C9	90.3 (4)	C9—C8—C10—C11	−0.6 (7)
N7—Pb1—N8—C9	10.0 (3)	C7—C8—C10—C11	−179.3 (5)
N2ⁱ—Pb1—N8—C9	42.9 (6)	C8—C10—C11—C12	−0.9 (8)
O2ⁱ—Pb1—N8—C9	−18.0 (5)	C9—N8—C12—C11	1.4 (8)
N4ⁱⁱ—Pb1—N8—C9	161.9 (4)	Pb1—N8—C12—C11	−172.7 (4)
C5—N7—C1—C2	−1.8 (8)	C10—C11—C12—N8	0.6 (8)
Pb1—N7—C1—C2	170.0 (4)

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

Experimental details

Crystal data
Chemical formula	[Pb₂(N₃)₃(NO₂)(C₁₂H₈N₂)₂]
M_r	946.89
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.6860 (5), 9.2056 (6), 9.9080 (7)
α, β, γ (°)	90.541 (1), 109.665 (1), 104.626 (1)
V (Å³)	635.32 (7)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	13.29
Crystal size (mm)	0.30 × 0.30 × 0.30

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.040, 0.109
No. of measured, independent and observed [I > 2σ(I)] reflections	6004, 2888, 2716
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.071, 1.03
No. of reflections	2888
No. of parameters	193
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.17, −1.97

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

Acknowledgements

We thank Shahid Beheshti University (project No. 600/2097) 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 (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Marandi, F., Mirtamizdoust, B., Chantrapromma, S. & Fun, H.-K. (2007). Z. Anorg. Allg. Chem. 633, 1329–1332. 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. (2010). J. Appl. Cryst. 43. Submitted. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.