Dichlorido-2κ2Cl-{μ-6,6′-dimeth­oxy-2,2′-[propane-1,3-diylbis(nitrilo­methyl­idyne)]diphenolato-1κ4O1,N,N′,O1′:2κ2O1,O1′}copper(II)zinc(II)

Liu, Q.; Ge, S.; Cui, G.

doi:10.1107/S1600536809006928

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page m359

doi:10.1107/S1600536809006928

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Dichlorido-2κ²Cl-{μ-6,6′-dimethoxy-2,2′-[propane-1,3-diylbis(nitrilomethylidyne)]diphenolato-1κ⁴O¹,N,N′,O^1′:2κ²O¹,O^1′}copper(II)zinc(II)

Qingyun Liu,^a ^* Shengsong Ge ^a and Guangwen Cui ^a

^aSchool of Chemical & Environmental Engineering, Shandong University of Science and Technology, Qingdao 266510, People's Republic of China
^*Correspondence e-mail: qyliusdu@163.com

(Received 21 February 2009; accepted 25 February 2009; online 6 March 2009)

In the title compound, [CuZnCl₂(C₁₉H₂₀N₂O₄)], the Cu^II ion exhibits a slightly distorted square-planar coordination geometry defined by two N atoms and two O atoms of the 6,6′-dimethoxy-2,2′-[propane-1,3-diylbis(nitrilomethylidyne)]diphenolate Schiff base ligand. The Zn^II ion is also four-coordinated by the two phenolate O atoms of the Schiff base ligand and by two cis-coordinated chloride anions.

Related literature

For the physical and chemical properties of heterometallic complexes, see: Ni et al. (2005 , 2007 ); Ward (2007 ) and for their roles in biological systems, see: Karlin (1993 ). For bond-length data, see: Korupoju et al. (2000 ); Gheorghe et al. (2006 ). For the restraints used in the refinement, see: Ng (2005 ).

Experimental

Crystal data

[CuZnCl₂(C₁₉H₂₀N₂O₄)]
M_r = 540.18
Orthorhombic, P c a 2₁
a = 13.0181 (9) Å
b = 10.8503 (8) Å
c = 14.7758 (11) Å
V = 2087.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.45 mm⁻¹
T = 298 K
0.20 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.744, T_max = 0.828
9818 measured reflections
3486 independent reflections
3084 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.074
S = 1.07
3486 reflections
262 parameters
13 restraints
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.58 e Å⁻³
Absolute structure: Flack (1983 ), 1564 Friedel pairs
Flack parameter: 0.006 (15)

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XP in SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006928/hg2482sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809006928/hg2482Isup2.hkl

checkCIF report

Comment top

Heterometallic complexes have been intensively focused on owing to their unique physical and chemical properties (Ward et al., 2007; Ni et al., 2005 and Ni et al. 2007). In addition, these compounds exist at the active sites of many metalloenzymes and play important roles in biological systems (Karlin, 1993). Whereas, it is necessary to further widen the system of heterometallic compounds. Herein, a new heterometallic dinuclear (Cu^IIZn^II) compound has been obtained. Its structure is depicted in the Figure 1.

Compound I is a dinuclear neutral complex with a slightly distorted planar configuration. The Cu^II atom is coordinated by two nitrogen atoms and two oxygen atoms from L^2- ligand forming a square-planar geometry. The coordination environment of each Zn^II atom is in a distorted tetrahedral geometry composed of two oxygen atoms from L^2- ligand and two chlorine atoms occupying the the other two positions. The dihedral angle of two aromatic rings is 26.90 (4)°. The Cu^II atom and Zn^II atom are connected via two bridging phenoxo oxygen atoms of L^2- ligand, The bond lengths of Cu—O, Cu—N, Zn—O and Zn—Cl are normal (Gheorghe et al. 2006 and Korupoju et al., 2000).

Related literature top

For the physical and chemical properties of heterometallic complexes, see: Ni et al. (2005, 2007); Ward (2007) and for their roles in biological systems, see: Karlin (1993). For bond-length data, see: Korupoju et al. (2000); Gheorghe et al. (2006). For the restraints used in the refinement, see: Ng (2005).

Experimental top

The H₂L ligand and complex CuL was synthesized according to the previous literature (Gheorghe et al. 2006). the synthesis method of the compound I was obtained by allowing a mixure of CuL (0.088 g, 0.2 mmol) and ZnCl₂.2H₂O(0.044 g, 0.2 mmol) to be stirred in the methanol solution at room temperature, cooled down to room temperature and then filtered. Suitable yellow needle-shaped crystals were obtained via slow evaporation of the filtrate at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XP in SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A view of (I) with the unique atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level, all hydrogen atoms are ommited for clarity.

Dichlorido-2κ²Cl-{µ-6,6'-dimethoxy-2,2'-[propane-1,3- diylbis(nitrilomethylidyne)]diphenolato- 1κ⁴O¹,N,N',O^1': 2κ²O¹,O^1'}copper(II)zinc(II) top

Crystal data top

[CuZnCl₂(C₁₉H₂₀N₂O₄)]	F(000) = 1092
M_r = 540.18	D_x = 1.719 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4074 reflections
a = 13.0181 (9) Å	θ = 2.5–26.1°
b = 10.8503 (8) Å	µ = 2.45 mm⁻¹
c = 14.7758 (11) Å	T = 298 K
V = 2087.1 (3) Å³	Needle, green
Z = 4	0.20 × 0.10 × 0.08 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3486 independent reflections
Radiation source: fine-focus sealed tube	3084 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 0 pixels mm^-1	θ_max = 25.0°, θ_min = 1.9°
ϕ and ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −11→12
T_min = 0.744, T_max = 0.828	l = −17→15
9818 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)] = 0.029	H-atom parameters constrained
wR(F²) = 0.074	w = 1/[σ²(F_o²) + (0.0389P)² + 0.0971P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
3486 reflections	Δρ_max = 0.63 e Å⁻³
262 parameters	Δρ_min = −0.58 e Å⁻³
13 restraints	Absolute structure: Flack (1983), 1564 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.006 (15)

Crystal data top

[CuZnCl₂(C₁₉H₂₀N₂O₄)]	V = 2087.1 (3) Å³
M_r = 540.18	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 13.0181 (9) Å	µ = 2.45 mm⁻¹
b = 10.8503 (8) Å	T = 298 K
c = 14.7758 (11) Å	0.20 × 0.10 × 0.08 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3486 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	3084 reflections with I > 2σ(I)
T_min = 0.744, T_max = 0.828	R_int = 0.025
9818 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	H-atom parameters constrained
wR(F²) = 0.074	Δρ_max = 0.63 e Å⁻³
S = 1.07	Δρ_min = −0.58 e Å⁻³
3486 reflections	Absolute structure: Flack (1983), 1564 Friedel pairs
262 parameters	Absolute structure parameter: 0.006 (15)
13 restraints

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	0.59914 (3)	0.74035 (3)	0.69902 (3)	0.04337 (13)
Cu1	0.59183 (3)	1.03456 (3)	0.71028 (4)	0.04411 (14)
Cl2	0.71295 (8)	0.63787 (10)	0.78281 (9)	0.0590 (3)
Cl1	0.48653 (8)	0.64556 (11)	0.60882 (10)	0.0653 (4)
O1	0.4768 (2)	0.6796 (3)	0.8322 (2)	0.0607 (8)
O4	0.7243 (2)	0.7042 (2)	0.5679 (2)	0.0531 (7)
O3	0.6649 (2)	0.9031 (2)	0.6508 (2)	0.0468 (7)
C6	0.3763 (3)	0.9888 (5)	0.8239 (3)	0.0537 (12)
N1	0.4874 (3)	1.1465 (3)	0.7582 (3)	0.0596 (10)
O2	0.5262 (2)	0.8915 (2)	0.76318 (19)	0.0442 (7)
C12	0.7778 (4)	1.1331 (3)	0.6360 (3)	0.0486 (10)
H12	0.8230	1.1989	0.6294	0.058*
C15	0.9470 (4)	0.9069 (4)	0.5223 (3)	0.0557 (11)
H15	1.0118	0.9054	0.4958	0.067*
C13	0.8147 (3)	1.0147 (3)	0.6042 (3)	0.0421 (9)
C7	0.4389 (3)	0.8850 (4)	0.8080 (3)	0.0445 (10)
C17	0.7914 (3)	0.8007 (4)	0.5642 (3)	0.0439 (9)
C5	0.2819 (3)	0.9734 (5)	0.8696 (3)	0.0650 (13)
H5	0.2399	1.0415	0.8793	0.078*
C18	0.7549 (3)	0.9076 (3)	0.6083 (3)	0.0388 (8)
C1	0.4576 (4)	0.5620 (4)	0.8709 (5)	0.0845 (18)
H1A	0.5132	0.5074	0.8566	0.127*
H1B	0.3947	0.5293	0.8469	0.127*
H1C	0.4518	0.5700	0.9354	0.127*
C3	0.3144 (3)	0.7587 (5)	0.8888 (3)	0.0633 (13)
H3	0.2943	0.6824	0.9113	0.076*
C16	0.8847 (3)	0.8003 (4)	0.5211 (3)	0.0534 (11)
H16	0.9069	0.7298	0.4910	0.064*
C11	0.6734 (4)	1.2928 (3)	0.6876 (5)	0.0794 (15)
H11A	0.7012	1.3144	0.7465	0.095*
H11B	0.7113	1.3392	0.6425	0.095*
C8	0.4053 (4)	1.1105 (4)	0.7987 (4)	0.0592 (13)
H8	0.3586	1.1722	0.8135	0.071*
C19	0.7605 (4)	0.5875 (4)	0.5382 (4)	0.0653 (13)
H19A	0.7066	0.5276	0.5440	0.098*
H19B	0.8181	0.5630	0.5747	0.098*
H19C	0.7814	0.5930	0.4761	0.098*
C2	0.4077 (3)	0.7705 (4)	0.8442 (3)	0.0506 (11)
N2	0.6914 (3)	1.1585 (3)	0.6717 (3)	0.0499 (9)
C10	0.5740 (5)	1.3279 (5)	0.6847 (5)	0.0981 (17)
H10A	0.5504	1.3104	0.6237	0.118*
H10B	0.5739	1.4168	0.6909	0.118*
C9	0.4950 (4)	1.2824 (4)	0.7450 (6)	0.098 (3)
H9A	0.4292	1.3114	0.7226	0.118*
H9B	0.5056	1.3199	0.8038	0.118*
C4	0.2511 (4)	0.8598 (5)	0.8999 (3)	0.0700 (14)
H4	0.1877	0.8508	0.9280	0.084*
C14	0.9123 (3)	1.0109 (5)	0.5619 (3)	0.0509 (11)
H14	0.9530	1.0813	0.5615	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0359 (2)	0.0315 (2)	0.0628 (3)	0.00014 (17)	0.0017 (2)	−0.0053 (2)
Cu1	0.0362 (2)	0.0294 (2)	0.0667 (3)	0.00258 (17)	−0.0002 (3)	−0.0082 (3)
Cl2	0.0442 (6)	0.0572 (6)	0.0758 (8)	0.0039 (5)	−0.0013 (5)	0.0129 (6)
Cl1	0.0448 (6)	0.0532 (7)	0.0980 (9)	0.0004 (5)	−0.0096 (6)	−0.0273 (6)
O1	0.0527 (18)	0.0442 (17)	0.085 (2)	−0.0085 (14)	0.0185 (16)	−0.0066 (16)
O4	0.0498 (17)	0.0346 (14)	0.075 (2)	0.0015 (13)	0.0136 (15)	−0.0052 (14)
O3	0.0392 (16)	0.0337 (13)	0.0674 (19)	−0.0005 (11)	0.0092 (14)	−0.0024 (12)
C6	0.039 (2)	0.065 (3)	0.057 (3)	0.009 (2)	0.001 (2)	−0.026 (2)
N1	0.042 (2)	0.0386 (19)	0.099 (3)	0.0044 (15)	−0.0035 (19)	−0.0215 (18)
O2	0.0354 (15)	0.0364 (15)	0.0608 (18)	0.0018 (11)	0.0114 (13)	−0.0094 (12)
C12	0.055 (3)	0.035 (2)	0.055 (2)	−0.0055 (18)	−0.009 (2)	0.0120 (18)
C15	0.040 (2)	0.073 (3)	0.054 (3)	0.002 (2)	0.011 (2)	0.007 (2)
C13	0.037 (2)	0.043 (2)	0.046 (2)	0.0038 (17)	−0.0034 (17)	0.0089 (18)
C7	0.032 (2)	0.052 (3)	0.049 (2)	0.0009 (17)	0.0005 (18)	−0.0173 (18)
C17	0.041 (2)	0.045 (2)	0.046 (2)	0.0089 (18)	0.0035 (18)	0.0039 (18)
C5	0.044 (3)	0.086 (4)	0.064 (3)	0.016 (3)	0.008 (2)	−0.031 (3)
C18	0.034 (2)	0.042 (2)	0.040 (2)	0.0014 (17)	−0.0036 (17)	0.0060 (17)
C1	0.080 (4)	0.046 (3)	0.128 (5)	−0.015 (3)	0.030 (4)	−0.007 (3)
C3	0.050 (3)	0.084 (3)	0.056 (3)	−0.014 (2)	0.016 (2)	−0.019 (3)
C16	0.054 (3)	0.058 (3)	0.048 (3)	0.006 (2)	0.010 (2)	0.000 (2)
C11	0.071 (3)	0.0296 (19)	0.138 (4)	0.0002 (19)	−0.006 (3)	−0.009 (3)
C8	0.049 (3)	0.053 (3)	0.075 (3)	0.017 (2)	−0.009 (2)	−0.031 (2)
C19	0.077 (3)	0.044 (2)	0.075 (3)	0.002 (2)	0.015 (3)	−0.004 (2)
C2	0.040 (2)	0.059 (3)	0.052 (3)	−0.0037 (19)	0.0075 (19)	−0.020 (2)
N2	0.0406 (18)	0.0318 (15)	0.077 (2)	−0.0013 (14)	−0.0081 (17)	−0.0010 (16)
C10	0.102 (3)	0.050 (2)	0.142 (4)	0.014 (2)	−0.011 (3)	−0.001 (3)
C9	0.058 (3)	0.035 (2)	0.201 (8)	0.011 (2)	0.000 (4)	−0.031 (3)
C4	0.051 (3)	0.097 (4)	0.062 (3)	−0.005 (3)	0.021 (2)	−0.022 (3)
C14	0.039 (2)	0.060 (3)	0.054 (3)	−0.006 (2)	0.0008 (19)	0.018 (2)

Geometric parameters (Å, º) top

Zn1—O3	2.088 (3)	C7—C2	1.412 (6)
Zn1—O2	2.119 (2)	C17—C16	1.371 (5)
Zn1—Cl2	2.2280 (12)	C17—C18	1.413 (5)
Zn1—Cl1	2.2324 (12)	C5—C4	1.371 (6)
Cu1—O3	1.926 (3)	C5—H5	0.9300
Cu1—O2	1.936 (3)	C1—H1A	0.9600
Cu1—N2	1.953 (3)	C1—H1B	0.9600
Cu1—N1	1.956 (4)	C1—H1C	0.9600
O1—C2	1.347 (5)	C3—C2	1.388 (6)
O1—C1	1.421 (6)	C3—C4	1.381 (6)
O4—C17	1.364 (5)	C3—H3	0.9300
O4—C19	1.421 (5)	C16—H16	0.9300
O3—C18	1.330 (5)	C11—C10	1.349 (7)
C6—C7	1.409 (6)	C11—N2	1.495 (5)
C6—C5	1.412 (7)	C11—H11A	0.9700
C6—C8	1.423 (7)	C11—H11B	0.9700
N1—C8	1.286 (6)	C8—H8	0.9300
N1—C9	1.490 (6)	C19—H19A	0.9600
O2—C7	1.318 (5)	C19—H19B	0.9600
C12—N2	1.272 (5)	C19—H19C	0.9600
C12—C13	1.450 (5)	C10—C9	1.448 (9)
C12—H12	0.9300	C10—H10A	0.9700
C15—C14	1.350 (6)	C10—H10B	0.9700
C15—C16	1.413 (6)	C9—H9A	0.9700
C15—H15	0.9300	C9—H9B	0.9700
C13—C18	1.400 (5)	C4—H4	0.9300
C13—C14	1.417 (6)	C14—H14	0.9300

O3—Zn1—O2	71.43 (10)	H1A—C1—H1B	109.5
O3—Zn1—Cl2	109.81 (8)	O1—C1—H1C	109.5
O2—Zn1—Cl2	115.82 (9)	H1A—C1—H1C	109.5
O3—Zn1—Cl1	117.09 (9)	H1B—C1—H1C	109.5
O2—Zn1—Cl1	109.24 (8)	C2—C3—C4	120.3 (5)
Cl2—Zn1—Cl1	122.58 (4)	C2—C3—H3	119.8
O3—Cu1—O2	78.97 (10)	C4—C3—H3	119.8
O3—Cu1—N2	92.81 (13)	C17—C16—C15	120.0 (4)
O2—Cu1—N2	164.28 (13)	C17—C16—H16	120.0
O3—Cu1—N1	165.52 (14)	C15—C16—H16	120.0
O2—Cu1—N1	92.58 (14)	C10—C11—N2	114.8 (4)
N2—Cu1—N1	98.00 (15)	C10—C11—H11A	108.6
C2—O1—C1	119.1 (4)	N2—C11—H11A	108.6
C17—O4—C19	117.3 (3)	C10—C11—H11B	108.6
C18—O3—Cu1	128.6 (2)	N2—C11—H11B	108.6
C18—O3—Zn1	123.6 (2)	H11A—C11—H11B	107.5
Cu1—O3—Zn1	105.55 (12)	N1—C8—C6	128.6 (4)
C7—C6—C5	119.2 (5)	N1—C8—H8	115.7
C7—C6—C8	123.0 (4)	C6—C8—H8	115.7
C5—C6—C8	117.7 (4)	O4—C19—H19A	109.5
C8—N1—C9	114.7 (4)	O4—C19—H19B	109.5
C8—N1—Cu1	123.9 (3)	H19A—C19—H19B	109.5
C9—N1—Cu1	121.4 (3)	O4—C19—H19C	109.5
C7—O2—Cu1	128.8 (2)	H19A—C19—H19C	109.5
C7—O2—Zn1	124.7 (2)	H19B—C19—H19C	109.5
Cu1—O2—Zn1	104.01 (11)	O1—C2—C3	125.5 (4)
N2—C12—C13	128.2 (4)	O1—C2—C7	113.7 (3)
N2—C12—H12	115.9	C3—C2—C7	120.8 (4)
C13—C12—H12	115.9	C12—N2—C11	114.5 (4)
C14—C15—C16	119.8 (4)	C12—N2—Cu1	123.9 (3)
C14—C15—H15	120.1	C11—N2—Cu1	121.4 (3)
C16—C15—H15	120.1	C11—C10—C9	124.4 (6)
C18—C13—C14	119.6 (4)	C11—C10—H10A	106.2
C18—C13—C12	122.5 (4)	C9—C10—H10A	106.2
C14—C13—C12	117.7 (4)	C11—C10—H10B	106.2
O2—C7—C6	122.6 (4)	C9—C10—H10B	106.2
O2—C7—C2	119.1 (3)	H10A—C10—H10B	106.4
C6—C7—C2	118.3 (4)	C10—C9—N1	117.7 (5)
O4—C17—C16	125.7 (4)	C10—C9—H9A	107.9
O4—C17—C18	113.3 (3)	N1—C9—H9A	107.9
C16—C17—C18	121.0 (4)	C10—C9—H9B	107.9
C4—C5—C6	121.1 (4)	N1—C9—H9B	107.9
C4—C5—H5	119.4	H9A—C9—H9B	107.2
C6—C5—H5	119.4	C5—C4—C3	120.0 (4)
O3—C18—C13	122.7 (3)	C5—C4—H4	120.0
O3—C18—C17	119.0 (3)	C3—C4—H4	120.0
C13—C18—C17	118.3 (4)	C15—C14—C13	121.1 (4)
O1—C1—H1A	109.5	C15—C14—H14	119.5
O1—C1—H1B	109.5	C13—C14—H14	119.5

Experimental details

Crystal data
Chemical formula	[CuZnCl₂(C₁₉H₂₀N₂O₄)]
M_r	540.18
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	298
a, b, c (Å)	13.0181 (9), 10.8503 (8), 14.7758 (11)
V (Å³)	2087.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.45
Crystal size (mm)	0.20 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.744, 0.828
No. of measured, independent and observed [I > 2σ(I)] reflections	9818, 3486, 3084
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.074, 1.07
No. of reflections	3486
No. of parameters	262
No. of restraints	13
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.58
Absolute structure	Flack (1983), 1564 Friedel pairs
Absolute structure parameter	0.006 (15)

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Science Foundation of Shandong Provincial Education Department (J08LC11), China.

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