Poly[[μ2-1,2-bis­(1H-imidazol-1-ylmeth­yl)benzene-κ2N3:N3′](μ2-tereph­thalato-κ2O1:O4)zinc(II)]

Zhang, S.-S.; Chen, L.-J.

doi:10.1107/S1600536810042406

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page m1456

https://doi.org/10.1107/S1600536810042406

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Poly[[μ₂-1,2-bis(1H-imidazol-1-ylmethyl)benzene-κ²N³:N^3′](μ₂-terephthalato-κ²O¹:O⁴)zinc(II)]

Shi-Shen Zhang ^a ^* and Li-Jiang Chen ^a

^aDepartment of Applied Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, People's Republic of China
^*Correspondence e-mail: zhangshishen@126.com

(Received 19 October 2010; accepted 19 October 2010; online 23 October 2010)

In the title coordination polymer, [Zn(C₈H₄O₄)(C₁₄H₁₄N₄)]_n, the Zn^II atom is coordinated by two N atoms from two 1,2-bis(imidazol-1-ylmethyl)benzene ligands as well as by the two O atoms from two terephthalate ligands, confering a tetrahedral coordination geometry. The bridging ligands generate a three-dimensional structure.

Related literature

For related structures, see: Fan et al. (2005 , 2006 ); Liu et al. (2007 , 2008a ,b , 2009 ); Yang et al. (2008 ).

Experimental

Crystal data

[Zn(C₈H₄O₄)(C₁₄H₁₄N₄)]
M_r = 467.79
Triclinic, $[P \overline 1]$
a = 10.132 (3) Å
b = 10.179 (3) Å
c = 11.169 (3) Å
α = 99.073 (4)°
β = 102.748 (4)°
γ = 112.974 (4)°
V = 995.5 (5) Å³
Z = 2
Mo Kα radiation
μ = 1.27 mm⁻¹
T = 291 K
0.20 × 0.16 × 0.10 mm

Data collection

Bruker SMART area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.785, T_max = 0.883
7505 measured reflections
3674 independent reflections
3140 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.097
S = 1.05
3674 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810042406/ng5050sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810042406/ng5050Isup2.hkl

checkCIF report

Comment top

Imidazol and its derivatives have been achieving rapidly increasing attention not only for their potential application as functional materials, but also for their intriguing variety of architectures and topologies. 1,2-bis(imidazole-1-ylmethyl)-benzene, as one kind of those ligand, has usually been used to construct a great variety of structurally interesting entities, such as one-dimensional chain, square grid, 2-fold interpenetrated, 3-fold interpenetrated network.

The asymmetric unit of the title compound (I) is illustrated in Fig. 1. Single-crystal X-ray diffraction shows that the asymmetric unit contains one Zn crystallographically nonequivalent atom.the Zn^II atom is coordinated by two N atoms from two 1,2-bis(imidazole-1-ylmethyl)-benzene ligands, as well as by the two O atoms from two terephthalic acid ligands to confer a distorted tetrahedral coordination at the metal centre. The two Zn atoms coordinated by two N atoms to form a layer. The layer three-dimensional structure is stabilized by intermolecular π-π stacking interaction and hydrogen bond.

Related literature top

For related structures, see: Fan et al. (2005, 2006); Liu et al. (2007, 2008a,b, 2009); Yang et al. (2008).

Experimental top

A mixture of ZnSO₄ (0.032 g, 0.2 nmol), 1,2-bis(imidazole-1-ylmethyl)-benzene(0.024 g, 0.1 nmol) and Terephthalic acid (0.016 g, 0.1 nmol) in mole ratio of 1:1:1 in water(6 ml) was sealed in 15 ml Teflon-lined reactor and heated to 180°C for 24 h and then cooled to room temperature at a rate of 5°C/h. the yellow block crystal was obtianed in the yield of 20%.

Structure description top

For related structures, see: Fan et al. (2005, 2006); Liu et al. (2007, 2008a,b, 2009); Yang et al. (2008).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound showing 30% probability ellipsoids.
	Fig. 2. The crystal packing of the title compound

Poly[[µ₂-1,2-bis(1H-imidazol-1-ylmethyl)benzene- κ²N³:N^3'](µ₂-terephthalato- κ²O¹:O⁴)zinc(II)] top

Crystal data top

[Zn(C₈H₄O₄)(C₁₄H₁₄N₄)]	Z = 2
M_r = 467.79	F(000) = 480
Triclinic, P1	D_x = 1.561 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.132 (3) Å	Cell parameters from 1793 reflections
b = 10.179 (3) Å	θ = 1.9–25.5°
c = 11.169 (3) Å	µ = 1.27 mm⁻¹
α = 99.073 (4)°	T = 291 K
β = 102.748 (4)°	Block, yellow
γ = 112.974 (4)°	0.20 × 0.16 × 0.10 mm
V = 995.5 (5) Å³

Data collection top

Bruker SMART area-detector diffractometer	3674 independent reflections
Radiation source: fine-focus sealed tube	3140 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
φ and ω scans	θ_max = 25.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.785, T_max = 0.883	k = −12→12
7505 measured reflections	l = −13→13

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0482P)² + 0.0138P] where P = (F_o² + 2F_c²)/3
3674 reflections	(Δ/σ)_max < 0.001
298 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

[Zn(C₈H₄O₄)(C₁₄H₁₄N₄)]	γ = 112.974 (4)°
M_r = 467.79	V = 995.5 (5) Å³
Triclinic, P1	Z = 2
a = 10.132 (3) Å	Mo Kα radiation
b = 10.179 (3) Å	µ = 1.27 mm⁻¹
c = 11.169 (3) Å	T = 291 K
α = 99.073 (4)°	0.20 × 0.16 × 0.10 mm
β = 102.748 (4)°

Data collection top

Bruker SMART area-detector diffractometer	3674 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3140 reflections with I > 2σ(I)
T_min = 0.785, T_max = 0.883	R_int = 0.027
7505 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.05	Δρ_max = 0.60 e Å⁻³
3674 reflections	Δρ_min = −0.23 e Å⁻³
298 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Zn1	0.72744 (4)	0.03060 (3)	−0.12258 (3)	0.03123 (13)
O1	0.8199 (2)	−0.0226 (2)	−0.24812 (18)	0.0371 (5)
O2	0.9037 (2)	0.2104 (2)	−0.2633 (2)	0.0458 (6)
O3	0.5956 (2)	−0.1577 (2)	−0.0977 (2)	0.0459 (6)
O4	0.8048 (3)	−0.1373 (2)	0.0314 (3)	0.0560 (6)
N1	0.5722 (3)	0.0954 (3)	−0.2066 (2)	0.0348 (6)
N2	0.8687 (3)	0.1981 (2)	0.0314 (2)	0.0337 (6)
N6	1.0855 (3)	0.3509 (3)	0.1741 (2)	0.0360 (6)
N9	0.4735 (3)	0.2181 (3)	−0.3094 (2)	0.0376 (6)
C1	0.9907 (4)	0.1328 (4)	−0.4772 (3)	0.0455 (8)
H1	0.9858	0.2230	−0.4625	0.073 (12)*
C4	0.8876 (3)	0.0814 (3)	−0.2957 (3)	0.0314 (6)
C6	0.9462 (3)	0.0392 (3)	−0.4010 (3)	0.0319 (7)
C9	0.9965 (3)	0.2102 (3)	0.1035 (3)	0.0360 (7)
H9	1.0222	0.1322	0.1055	0.045 (9)*
C10	0.6685 (4)	−0.2048 (3)	−0.0265 (3)	0.0382 (7)
C11	0.8774 (4)	0.3382 (3)	0.0577 (3)	0.0446 (8)
H11	0.8025	0.3636	0.0203	0.052 (10)*
C13	1.2799 (3)	0.5047 (3)	0.3833 (3)	0.0356 (7)
C18	1.4214 (3)	0.6254 (3)	0.4431 (3)	0.0394 (7)
C20	0.5801 (3)	−0.3584 (3)	−0.0123 (3)	0.0382 (7)
C22	1.3428 (5)	0.6714 (4)	0.6276 (3)	0.0633 (11)
H22	1.3647	0.7271	0.7097	0.067 (11)*
C23	1.1735 (4)	0.4697 (3)	0.4470 (3)	0.0420 (8)
H23	1.0795	0.3895	0.4065	0.035 (8)*
C26	0.5945 (3)	0.1929 (3)	−0.2730 (3)	0.0389 (7)
H26	0.6833	0.2390	−0.2922	0.030 (7)*
C27	0.4285 (3)	0.0549 (3)	−0.2007 (3)	0.0407 (7)
H27	0.3809	−0.0136	−0.1596	0.047 (9)*
C28	0.6533 (4)	−0.4224 (3)	0.0621 (3)	0.0443 (8)
H28	0.7563	−0.3708	0.1043	0.050 (10)*
C31	0.9565 (4)	−0.0932 (3)	−0.4253 (3)	0.0436 (8)
H31	0.9278	−0.1572	−0.3750	0.063 (11)*
C32	0.4269 (4)	−0.4382 (3)	−0.0747 (3)	0.0442 (8)
H32	0.3775	−0.3967	−0.1252	0.058 (10)*
C33	1.2432 (3)	0.4081 (4)	0.2513 (3)	0.0441 (8)
H33A	1.2660	0.3252	0.2594	0.063 (11)*
H33B	1.3073	0.4652	0.2071	0.042 (9)*
C37	1.0093 (4)	0.4329 (3)	0.1455 (3)	0.0443 (8)
H37	1.0422	0.5339	0.1795	0.038 (8)*
C38	1.2048 (4)	0.5524 (4)	0.5688 (3)	0.0547 (9)
H38	1.1325	0.5272	0.6106	0.040 (9)*
C39	1.4495 (4)	0.7073 (4)	0.5666 (3)	0.0562 (10)
H39	1.5423	0.7885	0.6075	0.065 (11)*
C45	0.4583 (3)	0.3249 (4)	−0.3803 (3)	0.0490 (9)
H45A	0.3600	0.2789	−0.4446	0.045 (9)*
H45B	0.4650	0.4104	−0.3222	0.045 (9)*
C46	0.3671 (4)	0.1301 (3)	−0.2636 (3)	0.0431 (8)
H46	0.2710	0.1233	−0.2735	0.052 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0359 (2)	0.0264 (2)	0.0302 (2)	0.01204 (16)	0.01047 (15)	0.00882 (14)
O1	0.0418 (12)	0.0331 (11)	0.0389 (12)	0.0145 (10)	0.0196 (10)	0.0115 (9)
O2	0.0562 (14)	0.0343 (12)	0.0543 (14)	0.0227 (11)	0.0270 (12)	0.0103 (10)
O3	0.0583 (15)	0.0309 (12)	0.0426 (13)	0.0103 (11)	0.0167 (11)	0.0174 (10)
O4	0.0445 (14)	0.0400 (14)	0.0877 (18)	0.0156 (11)	0.0265 (13)	0.0285 (13)
N1	0.0354 (14)	0.0328 (14)	0.0356 (14)	0.0136 (11)	0.0101 (11)	0.0127 (11)
N2	0.0378 (14)	0.0285 (13)	0.0316 (13)	0.0149 (11)	0.0062 (11)	0.0050 (11)
N6	0.0413 (15)	0.0303 (14)	0.0310 (13)	0.0149 (12)	0.0072 (12)	0.0021 (11)
N9	0.0292 (13)	0.0356 (14)	0.0442 (15)	0.0129 (11)	0.0050 (12)	0.0132 (12)
C1	0.065 (2)	0.0356 (18)	0.055 (2)	0.0290 (17)	0.0345 (18)	0.0205 (16)
C4	0.0277 (15)	0.0310 (16)	0.0322 (16)	0.0114 (13)	0.0076 (13)	0.0064 (13)
C6	0.0295 (15)	0.0303 (16)	0.0355 (16)	0.0108 (13)	0.0131 (13)	0.0099 (13)
C9	0.0442 (18)	0.0294 (16)	0.0335 (16)	0.0177 (14)	0.0108 (14)	0.0041 (13)
C10	0.047 (2)	0.0300 (17)	0.0406 (18)	0.0159 (15)	0.0230 (16)	0.0068 (14)
C11	0.054 (2)	0.0357 (18)	0.0436 (19)	0.0276 (17)	0.0028 (16)	0.0059 (15)
C13	0.0429 (18)	0.0308 (16)	0.0307 (16)	0.0170 (14)	0.0045 (14)	0.0095 (13)
C18	0.0387 (17)	0.0311 (16)	0.0396 (18)	0.0133 (14)	−0.0029 (14)	0.0138 (14)
C20	0.0467 (19)	0.0323 (16)	0.0418 (18)	0.0176 (15)	0.0227 (15)	0.0130 (14)
C22	0.090 (3)	0.050 (2)	0.0291 (19)	0.023 (2)	0.002 (2)	0.0006 (17)
C23	0.0468 (19)	0.0297 (17)	0.0389 (18)	0.0094 (15)	0.0094 (15)	0.0065 (14)
C26	0.0306 (17)	0.0350 (17)	0.052 (2)	0.0131 (14)	0.0115 (15)	0.0189 (15)
C27	0.0395 (18)	0.0410 (18)	0.0437 (18)	0.0156 (15)	0.0193 (15)	0.0142 (15)
C28	0.043 (2)	0.0381 (18)	0.053 (2)	0.0153 (16)	0.0167 (17)	0.0197 (16)
C31	0.059 (2)	0.0366 (18)	0.051 (2)	0.0241 (16)	0.0316 (17)	0.0223 (16)
C32	0.047 (2)	0.0376 (18)	0.053 (2)	0.0205 (16)	0.0159 (17)	0.0215 (16)
C33	0.0415 (19)	0.0430 (19)	0.0423 (19)	0.0166 (16)	0.0126 (16)	0.0033 (15)
C37	0.057 (2)	0.0293 (18)	0.0427 (18)	0.0209 (16)	0.0070 (17)	0.0055 (14)
C38	0.077 (3)	0.053 (2)	0.0397 (19)	0.030 (2)	0.023 (2)	0.0154 (17)
C39	0.059 (2)	0.040 (2)	0.040 (2)	0.0102 (18)	−0.0127 (18)	0.0063 (16)
C45	0.0325 (18)	0.040 (2)	0.064 (2)	0.0126 (15)	−0.0018 (17)	0.0198 (18)
C46	0.0337 (18)	0.0428 (19)	0.053 (2)	0.0159 (15)	0.0153 (15)	0.0129 (16)

Geometric parameters (Å, º) top

Zn1—O3	1.967 (2)	C13—C33	1.515 (4)
Zn1—O1	1.9680 (19)	C18—C39	1.399 (5)
Zn1—N2	1.999 (2)	C18—C45ⁱⁱ	1.497 (4)
Zn1—N1	2.036 (2)	C20—C32	1.384 (4)
O1—C4	1.283 (3)	C20—C28	1.393 (4)
O2—C4	1.240 (3)	C22—C39	1.364 (5)
O3—C10	1.244 (4)	C22—C38	1.369 (5)
O4—C10	1.234 (4)	C22—H22	0.9271
N1—C26	1.310 (3)	C23—C38	1.378 (4)
N1—C27	1.370 (4)	C23—H23	0.9299
N2—C9	1.313 (4)	C26—H26	0.9298
N2—C11	1.373 (4)	C27—C46	1.347 (4)
N6—C9	1.344 (3)	C27—H27	0.9297
N6—C37	1.369 (4)	C28—C32ⁱⁱⁱ	1.381 (4)
N6—C33	1.464 (4)	C28—H28	0.9299
N9—C26	1.339 (4)	C31—C1ⁱ	1.386 (4)
N9—C46	1.364 (4)	C31—H31	0.9294
N9—C45	1.478 (4)	C32—C28ⁱⁱⁱ	1.381 (4)
C1—C31ⁱ	1.386 (4)	C32—H32	0.9283
C1—C6	1.387 (4)	C33—H33A	0.9696
C1—H1	0.9289	C33—H33B	0.9695
C4—C6	1.506 (4)	C37—H37	0.9299
C6—C31	1.383 (4)	C38—H38	0.9292
C9—H9	0.9291	C39—H39	0.9280
C10—C20	1.522 (4)	C45—C18ⁱⁱ	1.497 (4)
C11—C37	1.340 (4)	C45—H45A	0.9699
C11—H11	0.9294	C45—H45B	0.9696
C13—C23	1.383 (4)	C46—H46	0.9284
C13—C18	1.398 (4)

O3—Zn1—O1	105.82 (9)	C28—C20—C10	120.3 (3)
O3—Zn1—N2	118.54 (9)	C39—C22—C38	120.2 (3)
O1—Zn1—N2	115.65 (9)	C39—C22—H22	119.6
O3—Zn1—N1	100.79 (10)	C38—C22—H22	120.1
O1—Zn1—N1	109.17 (9)	C38—C23—C13	120.9 (3)
N2—Zn1—N1	105.62 (10)	C38—C23—H23	119.8
C4—O1—Zn1	115.41 (18)	C13—C23—H23	119.2
C10—O3—Zn1	111.8 (2)	N1—C26—N9	111.6 (3)
C26—N1—C27	105.7 (2)	N1—C26—H26	124.3
C26—N1—Zn1	125.8 (2)	N9—C26—H26	124.2
C27—N1—Zn1	128.4 (2)	C46—C27—N1	109.2 (3)
C9—N2—C11	105.6 (2)	C46—C27—H27	125.4
C9—N2—Zn1	125.44 (19)	N1—C27—H27	125.3
C11—N2—Zn1	126.0 (2)	C32ⁱⁱⁱ—C28—C20	120.3 (3)
C9—N6—C37	107.5 (3)	C32ⁱⁱⁱ—C28—H28	119.8
C9—N6—C33	125.4 (3)	C20—C28—H28	120.0
C37—N6—C33	126.5 (3)	C6—C31—C1ⁱ	121.5 (3)
C26—N9—C46	106.8 (3)	C6—C31—H31	119.3
C26—N9—C45	127.3 (3)	C1ⁱ—C31—H31	119.2
C46—N9—C45	125.9 (3)	C28ⁱⁱⁱ—C32—C20	121.0 (3)
C31ⁱ—C1—C6	120.5 (3)	C28ⁱⁱⁱ—C32—H32	119.7
C31ⁱ—C1—H1	119.6	C20—C32—H32	119.3
C6—C1—H1	119.9	N6—C33—C13	113.4 (3)
O2—C4—O1	124.7 (3)	N6—C33—H33A	108.9
O2—C4—C6	119.0 (2)	C13—C33—H33A	108.9
O1—C4—C6	116.3 (2)	N6—C33—H33B	108.8
C31—C6—C1	118.0 (3)	C13—C33—H33B	109.0
C31—C6—C4	121.4 (3)	H33A—C33—H33B	107.7
C1—C6—C4	120.6 (3)	C11—C37—N6	105.9 (3)
N2—C9—N6	110.9 (3)	C11—C37—H37	126.8
N2—C9—H9	124.7	N6—C37—H37	127.2
N6—C9—H9	124.5	C22—C38—C23	119.7 (4)
O4—C10—O3	124.9 (3)	C22—C38—H38	120.3
O4—C10—C20	118.8 (3)	C23—C38—H38	120.0
O3—C10—C20	116.2 (3)	C22—C39—C18	121.5 (3)
C37—C11—N2	110.1 (3)	C22—C39—H39	119.3
C37—C11—H11	124.9	C18—C39—H39	119.3
N2—C11—H11	125.0	N9—C45—C18ⁱⁱ	111.3 (3)
C23—C13—C18	119.7 (3)	N9—C45—H45A	109.3
C23—C13—C33	119.4 (3)	C18ⁱⁱ—C45—H45A	109.5
C18—C13—C33	120.9 (3)	N9—C45—H45B	109.4
C13—C18—C39	118.0 (3)	C18ⁱⁱ—C45—H45B	109.4
C13—C18—C45ⁱⁱ	123.6 (3)	H45A—C45—H45B	108.0
C39—C18—C45ⁱⁱ	118.4 (3)	C27—C46—N9	106.7 (3)
C32—C20—C28	118.8 (3)	C27—C46—H46	126.5
C32—C20—C10	120.9 (3)	N9—C46—H46	126.8

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

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₄O₄)(C₁₄H₁₄N₄)]
M_r	467.79
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	10.132 (3), 10.179 (3), 11.169 (3)
α, β, γ (°)	99.073 (4), 102.748 (4), 112.974 (4)
V (Å³)	995.5 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.27
Crystal size (mm)	0.20 × 0.16 × 0.10

Data collection
Diffractometer	Bruker SMART area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.785, 0.883
No. of measured, independent and observed [I > 2σ(I)] reflections	7505, 3674, 3140
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.097, 1.05
No. of reflections	3674
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.23

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Qianjiang Talents Project of the Technology Office of Zhejiang Province (grant No. 2009R10029), the National Natural Science Foundation of China (grant No. 20803067) and the Zhejiang Provincial Top Academic Discipline of Applied Chemistry and Eco-Dyeing & Finishing Engineering (grant No. ZYG2010019).

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