catena-Poly[[bis­(1-methyl­imidazole-κN3)zinc(II)]-μ-isophthalato-κ2O1:O3]

Zhao, J.

doi:10.1107/S160053680803078X

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page m1335

doi:10.1107/S160053680803078X

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catena-Poly[[bis(1-methylimidazole-κN³)zinc(II)]-μ-isophthalato-κ²O¹:O³]

Juan Zhao ^a ^*

^aCollege of Mechanical Engineering, Qingdao Technological University, Qingdao 266033, People's Republic of China
^*Correspondence e-mail: zhaojuanqd@163.com

(Received 17 September 2008; accepted 24 September 2008; online 27 September 2008)

In the solid state, the title compound, [Zn(C₈H₄O₄)(C₄H₆N₂)₂]_n, exhibits the existence of polymeric zigzag chains extending along the a axis. Each Zn^II ion is coordinated by two N atoms [Zn—N = 1.996 (6) and 2.032 (5) Å] and two O atoms [Zn—O = 1.930 (4) and 1.976 (4) Å] in a distorted tetrahedral geometry. Weak C—H⋯O interactions contribute to the crystal packing stability.

Related literature

In the related zinc compound [Zn(isophthalato)(1-H-imidazole)₂] (Yang et al., 2002 ), the Zn^II ions also have a distorted tetrahedral environment.

Experimental

Crystal data

[Zn(C₈H₄O₄)(C₄H₆N₂)₂]
M_r = 393.72
Orthorhombic, P b c a
a = 9.6820 (19) Å
b = 13.224 (3) Å
c = 26.983 (5) Å
V = 3454.8 (12) Å³
Z = 8
Mo Kα radiation
μ = 1.45 mm⁻¹
T = 293 (2) K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
3091 measured reflections
2967 independent reflections
2041 reflections with I > 2σ(I)
R_int = 0.035
3 standard reflections every 100 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.207
S = 1.05
2967 reflections
220 parameters
40 restraints
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O3ⁱ	0.96	2.55	3.423 (10)	150
C4—H4B⋯O3ⁱ	0.93	2.31	3.150 (9)	150
C11—H11A⋯O2ⁱⁱ	0.93	2.54	3.457 (8)	171
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803078X/cv2451sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680803078X/cv2451Isup2.hkl

checkCIF report

Comment top

In the title compound, (I) (Fig. 1), the zinc(II) centers are bridged by carboxylate groups of isophthalate ligands. Each Zn^II ion is coordinated by two N [Zn—N2 = 1.996 (6) Å, Zn—N4 = 2.032 (5) Å] and two O [Zn—O1 = 1.930 (4) Å, Zn—O4 = 1.976 (4) Å] atoms in a distorted tetrahedral geometry. All these values agree well with those observed in [Zn(isophthalato)(1-H-imidazole)₂] (Yang et al., 2002). Each isophthalate dianion in (I) acts as a bidentate ligand to bridge two Zn^II atoms through two monodentate carboxylate groups, building a zigzag polymeric chain along the a axis. The metal–metal distance across each polymer backbone is 9.682 (7) Å.

In the crystal, weak C—H···O interactions contribute to the crystal packing stability. In the corresponding zinc compound [Zn(isophthalato)(1-H-imidazole)₂] (Yang et al., 2002), the Zn^II ions have a distorted tetrahedral environment.

Related literature top

In the corresponding zinc compound [Zn(isophthalato)(1-H-imidazole)₂] (Yang et al., 2002), the Zn^II ions have a distorted tetrahedral environment.

Experimental top

The reaction of ZnCl₂(0.68 g, 5 mmol) with isophthalic acid (0.83 g, 5 mmol) in an aqueous-alcohol (3:1) solution (40 ml) at 363 K for 30 minutes produced a blue solution, to which 1-methylimidazole (0.82 g, 10 mmol) was added. The reaction solution was kept at room temperature after stirring for an hour at 333 K. Colourless crystals were obtained after a few days.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. A portion of the polymeric chain in (I) showing the atomic numbering and 30% probability displacement ellipsoids.

catena-Poly[[bis(1-methylimidazole-κN³)zinc(II)]-µ-isophthalato- κ²O¹:O³] top

Crystal data top

[Zn(C₈H₄O₄)(C₄H₆N₂)₂]	F(000) = 1616
M_r = 393.72	D_x = 1.514 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 9.6820 (19) Å	θ = 10–14°
b = 13.224 (3) Å	µ = 1.45 mm⁻¹
c = 26.983 (5) Å	T = 293 K
V = 3454.8 (12) Å³	Block, colourless
Z = 8	0.20 × 0.10 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.036
Radiation source: fine-focus sealed tube	θ_max = 25.2°, θ_min = 1.5°
Graphite monochromator	h = 0→11
ω scans	k = 0→15
3091 measured reflections	l = 0→32
2967 independent reflections	3 standard reflections every 100 reflections
2041 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.207	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1255P)²] where P = (F_o² + 2F_c²)/3
2967 reflections	(Δ/σ)_max < 0.001
220 parameters	Δρ_max = 0.50 e Å⁻³
40 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

[Zn(C₈H₄O₄)(C₄H₆N₂)₂]	V = 3454.8 (12) Å³
M_r = 393.72	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.6820 (19) Å	µ = 1.45 mm⁻¹
b = 13.224 (3) Å	T = 293 K
c = 26.983 (5) Å	0.20 × 0.10 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.036
3091 measured reflections	3 standard reflections every 100 reflections
2967 independent reflections	intensity decay: none
2041 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.068	40 restraints
wR(F²) = 0.207	H-atom parameters constrained
S = 1.05	Δρ_max = 0.50 e Å⁻³
2967 reflections	Δρ_min = −0.61 e Å⁻³
220 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
Zn	0.18405 (6)	0.12667 (5)	0.12048 (3)	0.0338 (3)
N1	0.1883 (6)	0.3348 (5)	0.2326 (2)	0.0594 (17)
N2	0.1689 (5)	0.2071 (4)	0.1829 (2)	0.0434 (13)
N3	0.2381 (6)	0.3608 (4)	0.0199 (2)	0.0461 (14)
N4	0.1948 (5)	0.2244 (4)	0.06251 (18)	0.0358 (12)
O1	0.3326 (4)	0.0294 (4)	0.11870 (16)	0.0460 (12)
O2	0.4748 (4)	0.1603 (3)	0.12273 (18)	0.0510 (13)
O3	1.0442 (4)	−0.0567 (4)	0.1520 (2)	0.0680 (16)
O4	−0.0041 (4)	0.0763 (3)	0.10656 (16)	0.0440 (11)
C1	0.2355 (10)	0.4326 (6)	0.2511 (3)	0.081
H1A	0.3017	0.4605	0.2284	0.122*
H1B	0.2777	0.4239	0.2830	0.122*
H1C	0.1581	0.4776	0.2539	0.122*
C2	0.0944 (8)	0.2711 (7)	0.2534 (3)	0.079 (3)
H2A	0.0483	0.2798	0.2833	0.094*
C3	0.0821 (8)	0.1945 (7)	0.2223 (3)	0.071 (2)
H3A	0.0229	0.1399	0.2267	0.086*
C4	0.2306 (8)	0.2910 (6)	0.1911 (2)	0.0523 (18)
H4B	0.2976	0.3181	0.1703	0.063*
C5	0.2982 (8)	0.4589 (5)	0.0065 (3)	0.060 (2)
H5A	0.3727	0.4745	0.0288	0.089*
H5B	0.2287	0.5104	0.0089	0.089*
H5C	0.3326	0.4560	−0.0268	0.089*
C6	0.2723 (6)	0.3054 (5)	0.0588 (2)	0.0408 (15)
H6A	0.3427	0.3218	0.0809	0.049*
C7	0.1029 (8)	0.2310 (5)	0.0239 (3)	0.0568 (19)
H7A	0.0326	0.1849	0.0175	0.068*
C8	0.1294 (8)	0.3137 (5)	−0.0030 (3)	0.059 (2)
H8A	0.0835	0.3349	−0.0315	0.070*
C9	0.9641 (6)	−0.0064 (5)	0.1281 (2)	0.0361 (14)
C10	0.8172 (5)	−0.0403 (5)	0.1219 (2)	0.0328 (14)
C11	0.7891 (7)	−0.1438 (5)	0.1187 (2)	0.0436 (16)
H11A	0.8608	−0.1907	0.1190	0.052*
C12	0.6544 (7)	−0.1755 (5)	0.1151 (3)	0.060 (2)
H12A	0.6356	−0.2443	0.1126	0.072*
C13	0.5473 (7)	−0.1080 (5)	0.1151 (3)	0.0510 (18)
H13A	0.4572	−0.1318	0.1121	0.061*
C14	0.5702 (5)	−0.0054 (4)	0.1195 (2)	0.0301 (12)
C15	0.7082 (5)	0.0286 (4)	0.1222 (2)	0.0321 (13)
H15A	0.7265	0.0975	0.1242	0.039*
C16	0.4545 (6)	0.0702 (5)	0.1210 (2)	0.0340 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn	0.0166 (4)	0.0401 (4)	0.0446 (5)	0.0005 (3)	−0.0007 (3)	0.0023 (3)
N1	0.067 (4)	0.058 (3)	0.053 (3)	−0.018 (3)	0.016 (3)	−0.013 (3)
N2	0.032 (3)	0.056 (3)	0.043 (3)	−0.008 (2)	0.006 (2)	0.001 (2)
N3	0.051 (3)	0.052 (3)	0.035 (3)	−0.008 (3)	0.003 (3)	0.003 (3)
N4	0.024 (2)	0.043 (3)	0.041 (3)	−0.009 (2)	−0.009 (2)	0.006 (2)
O1	0.019 (2)	0.057 (3)	0.062 (3)	0.004 (2)	0.0020 (19)	0.003 (2)
O2	0.021 (2)	0.036 (2)	0.096 (4)	−0.0011 (19)	−0.001 (2)	0.004 (2)
O3	0.023 (2)	0.075 (3)	0.106 (4)	−0.001 (2)	−0.013 (3)	0.041 (3)
O4	0.020 (2)	0.049 (3)	0.063 (3)	−0.0021 (19)	−0.004 (2)	0.008 (2)
C1	0.081	0.081	0.081	0.000	0.000	0.000
C2	0.068 (5)	0.100 (6)	0.068 (5)	−0.024 (4)	0.038 (4)	−0.019 (4)
C3	0.064 (5)	0.081 (5)	0.069 (5)	−0.030 (4)	0.031 (4)	−0.006 (4)
C4	0.052 (4)	0.071 (4)	0.033 (3)	−0.010 (3)	0.015 (3)	−0.005 (3)
C5	0.069 (5)	0.054 (4)	0.056 (5)	−0.010 (4)	0.008 (4)	0.004 (4)
C6	0.034 (3)	0.051 (4)	0.037 (4)	−0.006 (3)	0.001 (3)	0.003 (3)
C7	0.053 (4)	0.054 (4)	0.063 (5)	−0.009 (4)	−0.017 (4)	0.005 (4)
C8	0.061 (5)	0.060 (5)	0.054 (5)	−0.004 (4)	−0.017 (4)	0.017 (4)
C9	0.017 (3)	0.046 (3)	0.045 (4)	0.006 (3)	0.000 (3)	−0.007 (3)
C10	0.011 (3)	0.054 (4)	0.033 (3)	−0.002 (2)	0.002 (2)	0.005 (3)
C11	0.026 (3)	0.041 (4)	0.064 (4)	0.005 (3)	−0.006 (3)	−0.007 (3)
C12	0.029 (4)	0.031 (3)	0.119 (7)	−0.006 (3)	−0.005 (4)	−0.006 (4)
C13	0.024 (3)	0.042 (4)	0.087 (5)	−0.005 (3)	−0.002 (3)	−0.007 (3)
C14	0.015 (3)	0.037 (3)	0.038 (3)	0.002 (2)	−0.004 (2)	0.001 (3)
C15	0.017 (3)	0.034 (3)	0.046 (4)	−0.001 (2)	−0.002 (2)	0.005 (3)
C16	0.012 (3)	0.049 (4)	0.041 (3)	0.001 (3)	0.001 (2)	0.008 (3)

Geometric parameters (Å, º) top

Zn—O1	1.930 (4)	C3—H3A	0.9300
Zn—O4	1.976 (4)	C4—H4B	0.9300
Zn—N2	1.996 (6)	C5—H5A	0.9600
Zn—N4	2.032 (5)	C5—H5B	0.9600
N1—C4	1.327 (8)	C5—H5C	0.9600
N1—C2	1.360 (9)	C6—H6A	0.9300
N1—C1	1.459 (10)	C7—C8	1.339 (9)
N2—C4	1.279 (8)	C7—H7A	0.9300
N2—C3	1.367 (8)	C8—H8A	0.9300
N3—C6	1.322 (8)	C9—O4ⁱⁱ	1.277 (8)
N3—C8	1.371 (9)	C9—C10	1.501 (7)
N3—C5	1.468 (8)	C10—C15	1.395 (8)
N4—C6	1.311 (7)	C10—C11	1.399 (9)
N4—C7	1.372 (8)	C11—C12	1.373 (8)
O1—C16	1.299 (7)	C11—H11A	0.9300
O2—C16	1.209 (8)	C12—C13	1.368 (9)
O3—C9	1.207 (7)	C12—H12A	0.9300
O4—C9ⁱ	1.277 (8)	C13—C14	1.381 (8)
C1—H1A	0.9600	C13—H13A	0.9300
C1—H1B	0.9600	C14—C15	1.411 (7)
C1—H1C	0.9600	C14—C16	1.502 (8)
C2—C3	1.319 (11)	C15—H15A	0.9300
C2—H2A	0.9300

O1—Zn—O4	117.23 (19)	H5A—C5—H5B	109.5
O1—Zn—N2	115.5 (2)	N3—C5—H5C	109.5
O4—Zn—N2	105.80 (19)	H5A—C5—H5C	109.5
O1—Zn—N4	111.51 (19)	H5B—C5—H5C	109.5
O4—Zn—N4	96.63 (18)	N4—C6—N3	111.7 (6)
N2—Zn—N4	108.3 (2)	N4—C6—H6A	124.2
C4—N1—C2	106.5 (6)	N3—C6—H6A	124.2
C4—N1—C1	125.3 (7)	C8—C7—N4	109.9 (6)
C2—N1—C1	128.2 (7)	C8—C7—H7A	125.1
C4—N2—C3	104.9 (6)	N4—C7—H7A	125.1
C4—N2—Zn	125.0 (5)	C7—C8—N3	105.8 (6)
C3—N2—Zn	129.6 (5)	C7—C8—H8A	127.1
C6—N3—C8	107.4 (5)	N3—C8—H8A	127.1
C6—N3—C5	125.9 (6)	O3—C9—O4ⁱⁱ	124.1 (6)
C8—N3—C5	126.5 (6)	O3—C9—C10	120.2 (6)
C6—N4—C7	105.2 (5)	O4ⁱⁱ—C9—C10	115.7 (5)
C6—N4—Zn	127.4 (4)	C15—C10—C11	119.5 (5)
C7—N4—Zn	126.2 (4)	C15—C10—C9	121.5 (6)
C16—O1—Zn	113.5 (4)	C11—C10—C9	118.9 (5)
C9ⁱ—O4—Zn	115.1 (4)	C12—C11—C10	119.2 (6)
N1—C1—H1A	109.5	C12—C11—H11A	120.4
N1—C1—H1B	109.5	C10—C11—H11A	120.4
H1A—C1—H1B	109.5	C13—C12—C11	121.4 (6)
N1—C1—H1C	109.5	C13—C12—H12A	119.3
H1A—C1—H1C	109.5	C11—C12—H12A	119.3
H1B—C1—H1C	109.5	C12—C13—C14	121.2 (6)
C3—C2—N1	105.9 (7)	C12—C13—H13A	119.4
C3—C2—H2A	127.0	C14—C13—H13A	119.4
N1—C2—H2A	127.0	C13—C14—C15	118.0 (5)
C2—C3—N2	110.2 (7)	C13—C14—C16	122.4 (5)
C2—C3—H3A	124.9	C15—C14—C16	119.5 (5)
N2—C3—H3A	124.9	C10—C15—C14	120.5 (5)
N2—C4—N1	112.4 (6)	C10—C15—H15A	119.7
N2—C4—H4B	123.8	C14—C15—H15A	119.7
N1—C4—H4B	123.8	O2—C16—O1	124.0 (6)
N3—C5—H5A	109.5	O2—C16—C14	122.4 (5)
N3—C5—H5B	109.5	O1—C16—C14	113.6 (5)

O1—Zn—N2—C4	89.0 (6)	Zn—N4—C6—N3	−169.7 (4)
O4—Zn—N2—C4	−139.6 (6)	C8—N3—C6—N4	0.9 (8)
N4—Zn—N2—C4	−36.9 (6)	C5—N3—C6—N4	176.2 (6)
O1—Zn—N2—C3	−100.1 (7)	C6—N4—C7—C8	1.9 (8)
O4—Zn—N2—C3	31.4 (7)	Zn—N4—C7—C8	170.1 (5)
N4—Zn—N2—C3	134.1 (7)	N4—C7—C8—N3	−1.4 (9)
O1—Zn—N4—C6	−81.7 (5)	C6—N3—C8—C7	0.3 (9)
O4—Zn—N4—C6	155.6 (5)	C5—N3—C8—C7	−175.0 (6)
N2—Zn—N4—C6	46.5 (6)	O3—C9—C10—C15	141.9 (7)
O1—Zn—N4—C7	112.7 (6)	O4ⁱⁱ—C9—C10—C15	−38.6 (9)
O4—Zn—N4—C7	−10.0 (6)	O3—C9—C10—C11	−34.3 (9)
N2—Zn—N4—C7	−119.1 (6)	O4ⁱⁱ—C9—C10—C11	145.2 (6)
O4—Zn—O1—C16	170.5 (4)	C15—C10—C11—C12	1.0 (10)
N2—Zn—O1—C16	−63.7 (4)	C9—C10—C11—C12	177.3 (6)
N4—Zn—O1—C16	60.4 (4)	C10—C11—C12—C13	−0.7 (12)
O1—Zn—O4—C9ⁱ	44.5 (5)	C11—C12—C13—C14	−1.0 (12)
N2—Zn—O4—C9ⁱ	−86.0 (4)	C12—C13—C14—C15	2.4 (11)
N4—Zn—O4—C9ⁱ	162.9 (4)	C12—C13—C14—C16	−178.4 (6)
C4—N1—C2—C3	−2.1 (10)	C11—C10—C15—C14	0.3 (9)
C1—N1—C2—C3	177.6 (8)	C9—C10—C15—C14	−175.9 (5)
N1—C2—C3—N2	1.5 (11)	C13—C14—C15—C10	−2.0 (10)
C4—N2—C3—C2	−0.2 (10)	C16—C14—C15—C10	178.7 (5)
Zn—N2—C3—C2	−172.6 (6)	Zn—O1—C16—O2	−1.8 (8)
C3—N2—C4—N1	−1.2 (9)	Zn—O1—C16—C14	−180.0 (4)
Zn—N2—C4—N1	171.6 (5)	C13—C14—C16—O2	−176.8 (7)
C2—N1—C4—N2	2.1 (9)	C15—C14—C16—O2	2.4 (9)
C1—N1—C4—N2	−177.6 (7)	C13—C14—C16—O1	1.4 (8)
C7—N4—C6—N3	−1.7 (7)	C15—C14—C16—O1	−179.4 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O3ⁱⁱⁱ	0.96	2.55	3.423 (10)	150
C4—H4B···O3ⁱⁱⁱ	0.93	2.31	3.150 (9)	150
C11—H11A···O2^iv	0.93	2.54	3.457 (8)	171

Symmetry codes: (iii) −x+3/2, y+1/2, z; (iv) −x+3/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₄O₄)(C₄H₆N₂)₂]
M_r	393.72
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	9.6820 (19), 13.224 (3), 26.983 (5)
V (Å³)	3454.8 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.45
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3091, 2967, 2041
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.598

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.207, 1.05
No. of reflections	2967
No. of parameters	220
No. of restraints	40
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.61

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (Sheldrick, 2008), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O3ⁱ	0.96	2.55	3.423 (10)	150
C4—H4B···O3ⁱ	0.93	2.31	3.150 (9)	150
C11—H11A···O2ⁱⁱ	0.93	2.54	3.457 (8)	171

Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) −x+3/2, y−1/2, z.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 20601015) and the Natural Science Foundation of Shandong Province (grant No. Y2006B12).

References

Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384–387. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, J., Zheng, S., Tao, J., Liu, G. & Chen, X. (2002). Aust. J. Chem. 55, 741–744. Web of Science CSD CrossRef CAS Google Scholar