Bis(4-acetyl-3-methyl-1-phenyl-1H-pyrazol-5-olato-κ2O,O′)bis­(N,N-dimethyl­formamide-κO)nickel(II)

Zhu, H.; Wei, Z.; Bu, L.; Xu, X.; Shi, J.

doi:10.1107/S1600536810026231

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m904

https://doi.org/10.1107/S1600536810026231

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Bis(4-acetyl-3-methyl-1-phenyl-1H-pyrazol-5-olato-κ²O,O′)bis(N,N-dimethylformamide-κO)nickel(II)

Hualing Zhu,^a ^* Zhen Wei,^a Luxia Bu,^a Xiaoping Xu ^a and Jun Shi ^a

^aDepartment of Basic Science, Tianjin Agriculturial College, Tianjin Jinjing Road No 22, Tianjin 300384, People's Republic of China
^*Correspondence e-mail: zhuhualing2004@126.com

(Received 29 June 2010; accepted 3 July 2010; online 10 July 2010)

The title complex, [Ni(C₁₂H₁₁N₂O₂)₂(C₃H₇NO)₂], lies on on an inversion center. The Ni^II ion is coordinated in a slightly distorted octahedral coordination enviroment by four O atoms from two bis-chelating 4-acety-3-methyl-1-phenyl-1H-pyrazol-5-olate ligands in the equatorial plane and two O atoms from two N,N-dimethylformamide ligands in the axial sites. In the crystal structure, weak intermolecular π–π stacking interactions with centroid–centroid distances of 3.7467 (13) Å link molecules into chains extending alongthe b axis.

Related literature

For related structures: Shi et al. (2005 ); Zhu et al. (2010a ,b , 2005 ).

Experimental

Crystal data

[Ni(C₁₂H₁₁N₂O₂)₂(C₃H₇NO)₂]
M_r = 635.36
Monoclinic, P 2₁ /n
a = 8.7201 (17) Å
b = 17.119 (3) Å
c = 9.852 (2) Å
β = 101.56 (3)°
V = 1440.9 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.73 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ) T_min = 0.868, T_max = 0.931
10320 measured reflections
2529 independent reflections
2279 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.078
S = 1.09
2529 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; 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/S1600536810026231/lh5075sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810026231/lh5075Isup2.hkl

checkCIF report

Comment top

As part of our onging studies of pyrazolone derivatives as potential ligands (Zhu et al., 2005; 2010a,b) we report the structure of the title complex, (I).

The molecular structure of the title complex is shown in Fig. 1. The Ni^II ion lies on a crystallographic inversion centre and adopts a slightly distorted octahedral coordination environment provided by four O atoms from two 4-acety-3-methyl-1-phenyl-1H-pyrazol-5(4H)- onato ligands in the equatorial plane two O atoms from two N,N-bimethylformamide ligands in the axial sites. A related complex has previously been published (Shi et al., 2005). In the crystal structure, weak intermolecular π–π stacking interactions involving the pyrazole rings, with centroid to centroid distances of 3.7467 (13)Å link molecules into one-dimensional chains (Fig 2).

Related literature top

For related structures: Shi et al. (2005); Zhu et al. (2010a,b, 2005).

Experimental top

The title compound was synthesized by dropping a nickel acetate (5m mol) ethanolic solution into an ethanolic solution of 4-acetyl-3-methyl-1-phenyl-1H-pyrazolone-5 (10m mol) and stirring for about 2 h under room temperature. The green blocks which were obtained were dried in air. The product was recrystallized from N,N-dimethylformamide which afforded crystals suitable for X–ray analysis.

Structure description top

As part of our onging studies of pyrazolone derivatives as potential ligands (Zhu et al., 2005; 2010a,b) we report the structure of the title complex, (I).

For related structures: Shi et al. (2005); Zhu et al. (2010a,b, 2005).

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); 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 molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius (symmetry code: (i) -x+1, -y+2, -z+1).
	Fig. 2. Part of the crystal structure showing intermolecular π–π interactions as dashed lines.

Bis(4-acetyl-3-methyl-1-phenyl-1H-pyrazol-5-olato- κ²O,O')bis(N,N-dimethylformamide- κO)nickel(II) top

Crystal data top

[Ni(C₁₂H₁₁N₂O₂)₂(C₃H₇NO)₂]	F(000) = 668
M_r = 635.36	D_x = 1.464 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4482 reflections
a = 8.7201 (17) Å	θ = 2.4–27.9°
b = 17.119 (3) Å	µ = 0.73 mm⁻¹
c = 9.852 (2) Å	T = 113 K
β = 101.56 (3)°	Block, green
V = 1440.9 (5) Å³	0.20 × 0.18 × 0.10 mm
Z = 2

Data collection top

Rigaku Saturn CCD diffractometer	2529 independent reflections
Radiation source: rotating anode	2279 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.031
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.0°, θ_min = 2.4°
ω and φ scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −19→20
T_min = 0.868, T_max = 0.931	l = −11→11
10320 measured reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.048P)² + 0.3836P] where P = (F_o² + 2F_c²)/3
2529 reflections	(Δ/σ)_max = 0.001
200 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

[Ni(C₁₂H₁₁N₂O₂)₂(C₃H₇NO)₂]	V = 1440.9 (5) Å³
M_r = 635.36	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.7201 (17) Å	µ = 0.73 mm⁻¹
b = 17.119 (3) Å	T = 113 K
c = 9.852 (2) Å	0.20 × 0.18 × 0.10 mm
β = 101.56 (3)°

Data collection top

Rigaku Saturn CCD diffractometer	2529 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	2279 reflections with I > 2σ(I)
T_min = 0.868, T_max = 0.931	R_int = 0.031
10320 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 1.09	Δρ_max = 0.32 e Å⁻³
2529 reflections	Δρ_min = −0.58 e Å⁻³
200 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
Ni1	0.5000	1.0000	0.5000	0.01056 (12)
O1	0.58951 (13)	1.05337 (7)	0.68398 (11)	0.0138 (3)
O2	0.41750 (13)	0.91066 (7)	0.60044 (12)	0.0145 (3)
O3	0.71254 (13)	0.94193 (7)	0.51507 (12)	0.0147 (3)
N1	0.71370 (16)	1.03649 (8)	0.91454 (14)	0.0136 (3)
N2	0.73040 (17)	0.97910 (9)	1.01841 (15)	0.0167 (3)
N3	0.92677 (16)	0.91367 (8)	0.42588 (15)	0.0141 (3)
C1	0.62073 (19)	1.01164 (9)	0.79249 (18)	0.0121 (4)
C2	0.57338 (19)	0.93439 (10)	0.82039 (18)	0.0134 (4)
C3	0.64609 (19)	0.91963 (10)	0.96176 (18)	0.0153 (4)
C4	0.6431 (2)	0.84786 (11)	1.04694 (19)	0.0208 (4)
H4A	0.7047	0.8567	1.1404	0.031*
H4B	0.6880	0.8041	1.0040	0.031*
H4C	0.5348	0.8356	1.0525	0.031*
C5	0.46612 (18)	0.88950 (10)	0.72430 (17)	0.0124 (4)
C6	0.4005 (2)	0.81431 (10)	0.76739 (18)	0.0185 (4)
H6A	0.3372	0.7888	0.6860	0.028*
H6B	0.3348	0.8254	0.8350	0.028*
H6C	0.4865	0.7797	0.8092	0.028*
C7	0.79488 (19)	1.10812 (10)	0.94735 (17)	0.0134 (4)
C8	0.74278 (19)	1.17723 (10)	0.87719 (17)	0.0145 (4)
H8	0.6550	1.1766	0.8025	0.017*
C9	0.8205 (2)	1.24649 (10)	0.91776 (18)	0.0177 (4)
H9	0.7846	1.2936	0.8709	0.021*
C10	0.9504 (2)	1.24833 (11)	1.02602 (19)	0.0206 (4)
H10	1.0017	1.2963	1.0544	0.025*
C11	1.0036 (2)	1.17911 (11)	1.09167 (18)	0.0212 (4)
H11	1.0938	1.1795	1.1640	0.025*
C12	0.9269 (2)	1.10923 (10)	1.05317 (18)	0.0174 (4)
H12	0.9646	1.0621	1.0990	0.021*
C13	0.78377 (19)	0.94216 (10)	0.41739 (18)	0.0138 (4)
H13	0.7326	0.9641	0.3316	0.017*
C14	1.0109 (2)	0.87896 (11)	0.5542 (2)	0.0208 (4)
H14A	0.9697	0.8998	0.6323	0.031*
H14B	1.1225	0.8916	0.5665	0.031*
H14C	0.9973	0.8221	0.5500	0.031*
C15	1.0048 (2)	0.91441 (11)	0.30838 (19)	0.0210 (4)
H15A	0.9379	0.9406	0.2298	0.031*
H15B	1.0247	0.8606	0.2826	0.031*
H15C	1.1044	0.9425	0.3337	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.01054 (17)	0.01073 (18)	0.00993 (18)	0.00035 (11)	0.00088 (12)	−0.00072 (11)
O1	0.0168 (6)	0.0137 (6)	0.0102 (6)	−0.0004 (5)	0.0011 (5)	0.0003 (5)
O2	0.0146 (6)	0.0137 (6)	0.0149 (7)	−0.0005 (4)	0.0023 (5)	−0.0013 (5)
O3	0.0136 (6)	0.0163 (6)	0.0145 (6)	0.0012 (5)	0.0035 (5)	−0.0007 (5)
N1	0.0177 (7)	0.0117 (8)	0.0104 (7)	−0.0010 (6)	0.0008 (6)	0.0010 (6)
N2	0.0196 (8)	0.0168 (8)	0.0123 (8)	−0.0003 (6)	−0.0004 (6)	0.0034 (6)
N3	0.0129 (7)	0.0145 (8)	0.0150 (7)	0.0012 (5)	0.0031 (6)	0.0008 (6)
C1	0.0097 (8)	0.0145 (9)	0.0122 (9)	0.0020 (6)	0.0022 (6)	−0.0020 (7)
C2	0.0131 (8)	0.0122 (9)	0.0149 (9)	0.0014 (6)	0.0028 (7)	0.0009 (7)
C3	0.0145 (8)	0.0154 (9)	0.0158 (9)	0.0002 (7)	0.0028 (7)	0.0003 (7)
C4	0.0226 (9)	0.0202 (10)	0.0177 (9)	−0.0033 (7)	−0.0006 (7)	0.0049 (8)
C5	0.0113 (8)	0.0128 (8)	0.0134 (9)	0.0039 (6)	0.0032 (7)	−0.0016 (7)
C6	0.0221 (9)	0.0156 (9)	0.0173 (9)	−0.0041 (7)	0.0030 (7)	−0.0005 (7)
C7	0.0147 (8)	0.0157 (9)	0.0106 (8)	−0.0015 (7)	0.0048 (7)	−0.0027 (7)
C8	0.0133 (8)	0.0163 (9)	0.0137 (9)	0.0001 (6)	0.0019 (7)	−0.0011 (7)
C9	0.0207 (9)	0.0152 (9)	0.0180 (9)	−0.0005 (7)	0.0060 (7)	0.0020 (7)
C10	0.0246 (9)	0.0190 (10)	0.0182 (10)	−0.0090 (8)	0.0039 (8)	−0.0015 (8)
C11	0.0196 (9)	0.0264 (11)	0.0151 (9)	−0.0068 (7)	−0.0024 (7)	0.0000 (8)
C12	0.0190 (9)	0.0170 (9)	0.0155 (9)	−0.0010 (7)	0.0018 (7)	0.0022 (7)
C13	0.0141 (8)	0.0104 (8)	0.0153 (9)	0.0000 (6)	−0.0010 (7)	−0.0010 (7)
C14	0.0160 (9)	0.0217 (10)	0.0234 (10)	0.0037 (7)	0.0007 (7)	0.0068 (8)
C15	0.0191 (9)	0.0236 (10)	0.0219 (10)	−0.0001 (7)	0.0083 (8)	−0.0008 (8)

Geometric parameters (Å, º) top

Ni1—O2ⁱ	2.0301 (12)	C5—C6	1.504 (2)
Ni1—O2	2.0301 (12)	C6—H6A	0.9800
Ni1—O1ⁱ	2.0402 (12)	C6—H6B	0.9800
Ni1—O1	2.0402 (12)	C6—H6C	0.9800
Ni1—O3ⁱ	2.0820 (12)	C7—C12	1.390 (3)
Ni1—O3	2.0820 (12)	C7—C8	1.399 (2)
O1—C1	1.269 (2)	C8—C9	1.384 (2)
O2—C5	1.262 (2)	C8—H8	0.9500
O3—C13	1.246 (2)	C9—C10	1.392 (3)
N1—C1	1.376 (2)	C9—H9	0.9500
N1—N2	1.405 (2)	C10—C11	1.385 (3)
N1—C7	1.420 (2)	C10—H10	0.9500
N2—C3	1.313 (2)	C11—C12	1.386 (3)
N3—C13	1.326 (2)	C11—H11	0.9500
N3—C14	1.455 (2)	C12—H12	0.9500
N3—C15	1.456 (2)	C13—H13	0.9500
C1—C2	1.428 (2)	C14—H14A	0.9800
C2—C5	1.417 (2)	C14—H14B	0.9800
C2—C3	1.432 (2)	C14—H14C	0.9800
C3—C4	1.491 (2)	C15—H15A	0.9800
C4—H4A	0.9800	C15—H15B	0.9800
C4—H4B	0.9800	C15—H15C	0.9800
C4—H4C	0.9800

O2ⁱ—Ni1—O2	180.0	O2—C5—C6	116.45 (15)
O2ⁱ—Ni1—O1ⁱ	90.81 (5)	C2—C5—C6	120.89 (15)
O2—Ni1—O1ⁱ	89.19 (5)	C5—C6—H6A	109.5
O2ⁱ—Ni1—O1	89.19 (5)	C5—C6—H6B	109.5
O2—Ni1—O1	90.81 (5)	H6A—C6—H6B	109.5
O1ⁱ—Ni1—O1	180.0	C5—C6—H6C	109.5
O2ⁱ—Ni1—O3ⁱ	90.17 (5)	H6A—C6—H6C	109.5
O2—Ni1—O3ⁱ	89.84 (5)	H6B—C6—H6C	109.5
O1ⁱ—Ni1—O3ⁱ	88.50 (5)	C12—C7—C8	119.80 (16)
O1—Ni1—O3ⁱ	91.50 (5)	C12—C7—N1	118.86 (15)
O2ⁱ—Ni1—O3	89.83 (5)	C8—C7—N1	121.32 (15)
O2—Ni1—O3	90.16 (5)	C9—C8—C7	119.33 (16)
O1ⁱ—Ni1—O3	91.50 (5)	C9—C8—H8	120.3
O1—Ni1—O3	88.50 (5)	C7—C8—H8	120.3
O3ⁱ—Ni1—O3	179.999 (1)	C8—C9—C10	121.12 (17)
C1—O1—Ni1	118.40 (11)	C8—C9—H9	119.4
C5—O2—Ni1	127.18 (11)	C10—C9—H9	119.4
C13—O3—Ni1	121.20 (11)	C11—C10—C9	118.91 (17)
C1—N1—N2	112.16 (14)	C11—C10—H10	120.5
C1—N1—C7	130.19 (14)	C9—C10—H10	120.5
N2—N1—C7	117.63 (14)	C10—C11—C12	120.87 (17)
C3—N2—N1	105.38 (14)	C10—C11—H11	119.6
C13—N3—C14	120.62 (15)	C12—C11—H11	119.6
C13—N3—C15	122.03 (15)	C11—C12—C7	119.92 (17)
C14—N3—C15	117.34 (14)	C11—C12—H12	120.0
O1—C1—N1	123.46 (15)	C7—C12—H12	120.0
O1—C1—C2	131.43 (16)	O3—C13—N3	123.95 (16)
N1—C1—C2	105.10 (14)	O3—C13—H13	118.0
C5—C2—C1	123.45 (16)	N3—C13—H13	118.0
C5—C2—C3	131.18 (16)	N3—C14—H14A	109.5
C1—C2—C3	105.17 (14)	N3—C14—H14B	109.5
N2—C3—C2	112.18 (15)	H14A—C14—H14B	109.5
N2—C3—C4	118.10 (16)	N3—C14—H14C	109.5
C2—C3—C4	129.68 (16)	H14A—C14—H14C	109.5
C3—C4—H4A	109.5	H14B—C14—H14C	109.5
C3—C4—H4B	109.5	N3—C15—H15A	109.5
H4A—C4—H4B	109.5	N3—C15—H15B	109.5
C3—C4—H4C	109.5	H15A—C15—H15B	109.5
H4A—C4—H4C	109.5	N3—C15—H15C	109.5
H4B—C4—H4C	109.5	H15A—C15—H15C	109.5
O2—C5—C2	122.64 (15)	H15B—C15—H15C	109.5

O2ⁱ—Ni1—O1—C1	−156.12 (12)	N1—N2—C3—C2	0.82 (19)
O2—Ni1—O1—C1	23.88 (12)	N1—N2—C3—C4	178.73 (15)
O1ⁱ—Ni1—O1—C1	20 (22)	C5—C2—C3—N2	−175.27 (17)
O3ⁱ—Ni1—O1—C1	113.74 (12)	C1—C2—C3—N2	−0.32 (19)
O3—Ni1—O1—C1	−66.26 (12)	C5—C2—C3—C4	7.1 (3)
O2ⁱ—Ni1—O2—C5	97 (5)	C1—C2—C3—C4	−177.93 (17)
O1ⁱ—Ni1—O2—C5	157.07 (13)	Ni1—O2—C5—C2	10.4 (2)
O1—Ni1—O2—C5	−22.93 (13)	Ni1—O2—C5—C6	−171.37 (10)
O3ⁱ—Ni1—O2—C5	−114.44 (13)	C1—C2—C5—O2	8.4 (3)
O3—Ni1—O2—C5	65.57 (13)	C3—C2—C5—O2	−177.46 (16)
O2ⁱ—Ni1—O3—C13	−39.74 (12)	C1—C2—C5—C6	−169.79 (15)
O2—Ni1—O3—C13	140.26 (12)	C3—C2—C5—C6	4.4 (3)
O1ⁱ—Ni1—O3—C13	51.07 (13)	C1—N1—C7—C12	−154.26 (17)
O1—Ni1—O3—C13	−128.93 (13)	N2—N1—C7—C12	23.8 (2)
O3ⁱ—Ni1—O3—C13	82 (18)	C1—N1—C7—C8	26.9 (3)
C1—N1—N2—C3	−1.06 (18)	N2—N1—C7—C8	−155.00 (15)
C7—N1—N2—C3	−179.46 (14)	C12—C7—C8—C9	−2.4 (2)
Ni1—O1—C1—N1	164.19 (12)	N1—C7—C8—C9	176.44 (15)
Ni1—O1—C1—C2	−16.5 (2)	C7—C8—C9—C10	0.7 (2)
N2—N1—C1—O1	−179.70 (14)	C8—C9—C10—C11	1.3 (3)
C7—N1—C1—O1	−1.6 (3)	C9—C10—C11—C12	−1.6 (3)
N2—N1—C1—C2	0.86 (18)	C10—C11—C12—C7	0.0 (3)
C7—N1—C1—C2	179.00 (16)	C8—C7—C12—C11	2.0 (2)
O1—C1—C2—C5	−4.3 (3)	N1—C7—C12—C11	−176.81 (15)
N1—C1—C2—C5	175.11 (15)	Ni1—O3—C13—N3	172.39 (12)
O1—C1—C2—C3	−179.71 (17)	C14—N3—C13—O3	0.4 (3)
N1—C1—C2—C3	−0.33 (17)	C15—N3—C13—O3	179.29 (16)

Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₂H₁₁N₂O₂)₂(C₃H₇NO)₂]
M_r	635.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	8.7201 (17), 17.119 (3), 9.852 (2)
β (°)	101.56 (3)
V (Å³)	1440.9 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.73
Crystal size (mm)	0.20 × 0.18 × 0.10

Data collection
Diffractometer	Rigaku Saturn CCD
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2008)
T_min, T_max	0.868, 0.931
No. of measured, independent and observed [I > 2σ(I)] reflections	10320, 2529, 2279
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.078, 1.09
No. of reflections	2529
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.58

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors thank the Science Development Committee of Tianjin Agricultural College (research grant No. 2007029) and the Doctor Degree Fund Commission of Tianjin Agricultural College (No. 2007027) for partial funding.

References

Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, J. M., Zhang, F. X., Wu, C. J. & Liu, L. D. (2005). Acta Cryst. E61, m2320–m2321. Web of Science CSD CrossRef IUCr Journals Google Scholar
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