{μ2-1,4-Bis[2-(4-pyrid­yl)ethen­yl]benzene-κ2N:N′}bis­[bis­(acetyl­acetonato-κ2O,O′)copper(II)]

Jian, F.-F.; Wang, J.; Zhang, J.

doi:10.1107/S1600536809048582

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1630

doi:10.1107/S1600536809048582

Open

access

{μ₂-1,4-Bis[2-(4-pyridyl)ethenyl]benzene-κ²N:N′}bis[bis(acetylacetonato-κ²O,O′)copper(II)]

Fang-Fang Jian,^a ^* Jing Wang ^b and Jing Zhang ^b

^aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China, and ^bNew Materials and Function Coordination Chemistry Laboratory, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
^*Correspondence e-mail: ffj2003@163169.com

(Received 5 November 2009; accepted 16 November 2009; online 21 November 2009)

The asymmetric unit of the title compound, [Cu₂(C₅H₇O₂)₄(C₂₀H₁₆N₂)], contains half of a centrosymmetric dinuclear molecule. In the molecule, each Cu center is coordinated by four O atoms from two acetylacetonate ligands and one N atom from the bridging linear 1,4-bis[2-(4-pyridyl)ethenyl]benzene ligand in a square-pyramidal geometry. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link molecules into sheets parallel to the bc plane.

Related literature

For coordination complexes with interesting topologies or properties, see: Ma et al. (2009 ); Liu et al. (2008 ). For long ligands, see: Banfi et al. (2002 ); Niu et al. (2001 ); Coe et al. (2006 ).

Experimental

Crystal data

[Cu₂(C₅H₇O₂)₄(C₂₀H₁₆N₂)]
M_r = 807.85
Monoclinic, P 2₁ /c
a = 7.9584 (16) Å
b = 18.594 (4) Å
c = 15.063 (4) Å
β = 120.97 (2)°
V = 1911.2 (8) Å³
Z = 2
Mo Kα radiation
μ = 1.17 mm⁻¹
T = 293 K
0.25 × 0.21 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.759, T_max = 0.800
7784 measured reflections
3352 independent reflections
2807 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.113
S = 0.99
3352 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O2ⁱ	0.93	2.45	3.371 (4)	173
C16—H16A⋯O1ⁱⁱ	0.93	2.52	3.333 (4)	147
C16—H16A⋯O3ⁱⁱ	0.93	2.58	3.315 (4)	136
Symmetry codes: (i) -x+1, -y, -z; (ii) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); 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 global, I. DOI: 10.1107/S1600536809048582/cv2655sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048582/cv2655Isup2.hkl

checkCIF report

Comment top

Metal ions and organic ligands are considered as the most important factors for designing the coordination networks (Ma et al., 2009). Up to now, it is still a challenge to predict the exact structure and understand the roles of both factors in crystal engineering. The flexible bridging ligands can afford different conformation with interesting topologies or properties (Liu et al., 2008). Among the others, long bis(pyridyl) ligands are used to construct the connectivity and geometry with different coordination sites metal ions, and often lead to interesting structural motifs (Ma et al., 2009). A large number of examples of particularly long ligands - 1,4-phenylenebis(4-pyridylmethanone), bis(4-pyridyl)terephthalate (Banfi et al., 2002), N,N^'-bis(4-pyridylmethyl)piperazine (Niu et al., 2001), N-phenyl-1,4-bis(E-2-(4-pyridyl)ethenyl)benzene (Coe et al., 2006), have been adopted for the self-assembly of coordination polymers, such as one-dimensional coordination chains, double helices, two dimensional layered structures, interpenetrated ladders, interpenetrated frameworks and so on (Banfi et al., 2002). Herein, we present the shoulder-pole coordination compound based on 1,4-bis(2-(4-pyridyl)ethenyl)benzole (bpyph) ligand, and describe its crystal structure.

In the title structure (Fig. 1),each Cu center is coordinated by four O atoms and one N atom from the bpyph ligand in a distorted pyramidal geometry. The linear bpyph ligand links two acetylacetonate copper(II) by Cu—N bonds, displaying the shoulder-pole model. In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) link molecules into sheets parallel to bc plane.

Related literature top

For coordination complexes with interesting topologies or properties, see: Ma et al. (2009); Liu et al. (2008). For long ligands, see: Banfi et al. (2002); Niu et al. (2001); Coe et al. (2006).

Experimental top

1,4-Bis(2-(4-pyridyl)ethenyl)benzene (2.84 g, 0.01 mol) and acetylacetonate copper(II) (5.23 g, 0.02 mol) in 2:1 molar ratio was dissolved in ethanol solution (40 ml) and refluxed for 2 h. After cooling and filtering, the blue block crystals were collected after 4 days (yield 42.35%).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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-labeling scheme [symmetry code: (A) 1-x, -y, 1-z]. H atoms omited for clarity. Displacement ellipsoids are drawn at the 30% probability level.

{µ₂-1,4-Bis[2-(4-pyridyl)ethenyl]benzene- κ²N:N'}bis[bis(acetylacetonato- κ²O,O')copper(II)] top

Crystal data top

[Cu₂(C₅H₇O₂)₄(C₂₀H₁₆N₂)]	F(000) = 840
M_r = 807.85	D_x = 1.404 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1253 reflections
a = 7.9584 (16) Å	θ = 1.9–25.0°
b = 18.594 (4) Å	µ = 1.17 mm⁻¹
c = 15.063 (4) Å	T = 293 K
β = 120.97 (2)°	Block, blue
V = 1911.2 (8) Å³	0.25 × 0.21 × 0.20 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	3352 independent reflections
Radiation source: fine-focus sealed tube	2807 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
phi and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −9→5
T_min = 0.759, T_max = 0.800	k = −22→20
7784 measured reflections	l = −17→17

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0573P)² + 1.3432P] where P = (F_o² + 2F_c²)/3
3352 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

[Cu₂(C₅H₇O₂)₄(C₂₀H₁₆N₂)]	V = 1911.2 (8) Å³
M_r = 807.85	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9584 (16) Å	µ = 1.17 mm⁻¹
b = 18.594 (4) Å	T = 293 K
c = 15.063 (4) Å	0.25 × 0.21 × 0.20 mm
β = 120.97 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3352 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	2807 reflections with I > 2σ(I)
T_min = 0.759, T_max = 0.800	R_int = 0.022
7784 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 0.99	Δρ_max = 0.41 e Å⁻³
3352 reflections	Δρ_min = −0.19 e Å⁻³
235 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
Cu1	0.51253 (5)	−0.173135 (19)	−0.13916 (3)	0.04299 (16)
O1	0.3204 (3)	−0.25040 (12)	−0.18542 (17)	0.0531 (6)
O2	0.3110 (3)	−0.10340 (12)	−0.22282 (18)	0.0586 (6)
O3	0.7113 (3)	−0.24740 (12)	−0.09329 (17)	0.0564 (6)
O4	0.6960 (3)	−0.09862 (12)	−0.12417 (19)	0.0604 (6)
N1	0.5307 (4)	−0.15375 (13)	0.01154 (18)	0.0414 (6)
C1	0.0211 (6)	−0.0532 (3)	−0.3578 (4)	0.0995 (16)
H1A	0.1015	−0.0110	−0.3323	0.149*
H1B	−0.0934	−0.0470	−0.3527	0.149*
H1C	−0.0177	−0.0609	−0.4288	0.149*
C2	0.1362 (5)	−0.1177 (2)	−0.2939 (3)	0.0629 (9)
C3	0.0540 (5)	−0.1850 (2)	−0.3146 (3)	0.0691 (11)
H3A	−0.0755	−0.1890	−0.3684	0.083*
C4	0.1463 (5)	−0.2471 (2)	−0.2628 (3)	0.0579 (9)
C5	0.0410 (7)	−0.3181 (2)	−0.2979 (4)	0.0868 (14)
H5A	0.1251	−0.3558	−0.2540	0.130*
H5B	0.0066	−0.3271	−0.3681	0.130*
H5C	−0.0757	−0.3165	−0.2942	0.130*
C6	0.9651 (7)	−0.0436 (3)	−0.1201 (4)	0.1045 (17)
H6A	0.8839	−0.0022	−0.1323	0.157*
H6B	0.9885	−0.0490	−0.1763	0.157*
H6C	1.0878	−0.0374	−0.0565	0.157*
C7	0.8632 (6)	−0.1098 (2)	−0.1128 (3)	0.0648 (10)
C8	0.9518 (6)	−0.1755 (2)	−0.0957 (3)	0.0747 (12)
H8A	1.0737	−0.1769	−0.0901	0.090*
C9	0.8778 (5)	−0.2392 (2)	−0.0861 (3)	0.0623 (10)
C10	0.9943 (7)	−0.3073 (3)	−0.0657 (4)	0.0896 (14)
H10A	0.9217	−0.3470	−0.0616	0.134*
H10B	1.1167	−0.3029	−0.0015	0.134*
H10C	1.0187	−0.3154	−0.1210	0.134*
C11	0.4967 (5)	−0.20205 (18)	0.0647 (2)	0.0505 (8)
H11A	0.4738	−0.2492	0.0409	0.061*
C12	0.4930 (5)	−0.18686 (17)	0.1532 (2)	0.0519 (8)
H12A	0.4707	−0.2235	0.1879	0.062*
C13	0.5224 (4)	−0.11714 (16)	0.1905 (2)	0.0434 (7)
C14	0.5614 (5)	−0.06650 (17)	0.1356 (2)	0.0514 (8)
H14A	0.5842	−0.0188	0.1573	0.062*
C15	0.5661 (5)	−0.08703 (17)	0.0498 (2)	0.0513 (8)
H15A	0.5959	−0.0522	0.0157	0.062*
C16	0.5141 (5)	−0.10005 (17)	0.2825 (2)	0.0488 (8)
H16A	0.5061	−0.1388	0.3192	0.059*
C17	0.5167 (5)	−0.03530 (16)	0.3193 (2)	0.0451 (7)
H17A	0.5261	0.0034	0.2830	0.054*
C18	0.5065 (4)	−0.01843 (16)	0.4102 (2)	0.0420 (7)
C19	0.5343 (5)	0.05182 (16)	0.4469 (2)	0.0501 (8)
H19A	0.5577	0.0877	0.4115	0.060*
C20	0.4717 (5)	−0.07005 (17)	0.4662 (2)	0.0505 (8)
H20A	0.4522	−0.1177	0.4444	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0456 (2)	0.0468 (2)	0.0388 (2)	0.00112 (16)	0.02331 (18)	−0.00511 (16)
O1	0.0523 (14)	0.0536 (13)	0.0514 (13)	−0.0059 (10)	0.0252 (11)	−0.0089 (10)
O2	0.0541 (15)	0.0537 (14)	0.0549 (14)	0.0064 (11)	0.0186 (12)	−0.0004 (11)
O3	0.0531 (14)	0.0571 (14)	0.0565 (14)	0.0087 (11)	0.0263 (12)	−0.0045 (11)
O4	0.0600 (15)	0.0584 (14)	0.0720 (16)	−0.0050 (11)	0.0405 (13)	−0.0016 (12)
N1	0.0477 (15)	0.0439 (14)	0.0347 (13)	0.0026 (11)	0.0226 (11)	−0.0037 (10)
C1	0.073 (3)	0.101 (4)	0.094 (4)	0.027 (3)	0.021 (3)	0.024 (3)
C2	0.054 (2)	0.080 (3)	0.052 (2)	0.0147 (19)	0.0260 (18)	0.0080 (18)
C3	0.045 (2)	0.093 (3)	0.055 (2)	−0.006 (2)	0.0155 (17)	0.003 (2)
C4	0.055 (2)	0.077 (2)	0.049 (2)	−0.0143 (18)	0.0314 (18)	−0.0138 (18)
C5	0.076 (3)	0.094 (3)	0.084 (3)	−0.035 (2)	0.037 (3)	−0.021 (2)
C6	0.088 (3)	0.118 (4)	0.122 (4)	−0.030 (3)	0.065 (3)	0.000 (3)
C7	0.059 (2)	0.089 (3)	0.053 (2)	−0.012 (2)	0.0331 (19)	−0.0033 (19)
C8	0.050 (2)	0.103 (3)	0.078 (3)	0.007 (2)	0.038 (2)	0.008 (2)
C9	0.053 (2)	0.089 (3)	0.0406 (18)	0.019 (2)	0.0211 (17)	−0.0028 (18)
C10	0.077 (3)	0.110 (4)	0.084 (3)	0.037 (3)	0.043 (3)	0.008 (3)
C11	0.064 (2)	0.0442 (17)	0.0515 (19)	−0.0086 (15)	0.0354 (17)	−0.0137 (15)
C12	0.076 (2)	0.0423 (17)	0.052 (2)	−0.0084 (15)	0.0434 (19)	−0.0021 (14)
C13	0.0547 (19)	0.0422 (16)	0.0375 (16)	0.0041 (14)	0.0269 (14)	−0.0002 (13)
C14	0.083 (2)	0.0383 (17)	0.0457 (18)	0.0030 (16)	0.0419 (18)	−0.0020 (13)
C15	0.076 (2)	0.0444 (18)	0.0431 (17)	0.0049 (16)	0.0371 (17)	0.0047 (14)
C16	0.071 (2)	0.0450 (18)	0.0416 (17)	0.0018 (15)	0.0368 (16)	0.0023 (13)
C17	0.061 (2)	0.0444 (17)	0.0392 (16)	0.0014 (14)	0.0329 (15)	0.0028 (13)
C18	0.0495 (18)	0.0436 (16)	0.0356 (15)	0.0021 (13)	0.0239 (14)	−0.0014 (13)
C19	0.075 (2)	0.0424 (17)	0.0457 (18)	−0.0034 (15)	0.0401 (17)	0.0014 (13)
C20	0.074 (2)	0.0399 (17)	0.0471 (18)	−0.0049 (15)	0.0379 (17)	−0.0075 (14)

Geometric parameters (Å, º) top

Cu1—O2	1.939 (2)	C7—C8	1.367 (5)
Cu1—O4	1.940 (2)	C8—C9	1.363 (6)
Cu1—O3	1.940 (2)	C8—H8A	0.9300
Cu1—O1	1.947 (2)	C9—C10	1.504 (5)
Cu1—N1	2.228 (2)	C10—H10A	0.9600
O1—C4	1.273 (4)	C10—H10B	0.9600
O2—C2	1.273 (4)	C10—H10C	0.9600
O3—C9	1.282 (4)	C11—C12	1.378 (4)
O4—C7	1.269 (4)	C11—H11A	0.9300
N1—C11	1.320 (4)	C12—C13	1.384 (4)
N1—C15	1.335 (4)	C12—H12A	0.9300
C1—C2	1.515 (5)	C13—C14	1.389 (4)
C1—H1A	0.9600	C13—C16	1.456 (4)
C1—H1B	0.9600	C14—C15	1.368 (4)
C1—H1C	0.9600	C14—H14A	0.9300
C2—C3	1.371 (5)	C15—H15A	0.9300
C3—C4	1.376 (5)	C16—C17	1.321 (4)
C3—H3A	0.9300	C16—H16A	0.9300
C4—C5	1.505 (5)	C17—C18	1.448 (4)
C5—H5A	0.9600	C17—H17A	0.9300
C5—H5B	0.9600	C18—C19	1.391 (4)
C5—H5C	0.9600	C18—C20	1.397 (4)
C6—C7	1.511 (6)	C19—C20ⁱ	1.376 (4)
C6—H6A	0.9600	C19—H19A	0.9300
C6—H6B	0.9600	C20—C19ⁱ	1.376 (4)
C6—H6C	0.9600	C20—H20A	0.9300

O2—Cu1—O4	85.37 (10)	O4—C7—C6	114.9 (4)
O2—Cu1—O3	163.25 (10)	C8—C7—C6	119.9 (4)
O4—Cu1—O3	92.29 (11)	C9—C8—C7	125.9 (4)
O2—Cu1—O1	91.51 (10)	C9—C8—H8A	117.0
O4—Cu1—O1	166.93 (10)	C7—C8—H8A	117.0
O3—Cu1—O1	87.05 (10)	O3—C9—C8	125.4 (3)
O2—Cu1—N1	98.77 (10)	O3—C9—C10	114.7 (4)
O4—Cu1—N1	96.62 (10)	C8—C9—C10	119.9 (4)
O3—Cu1—N1	97.98 (9)	C9—C10—H10A	109.5
O1—Cu1—N1	96.40 (9)	C9—C10—H10B	109.5
C4—O1—Cu1	125.2 (2)	H10A—C10—H10B	109.5
C2—O2—Cu1	125.9 (2)	C9—C10—H10C	109.5
C9—O3—Cu1	124.3 (2)	H10A—C10—H10C	109.5
C7—O4—Cu1	124.9 (2)	H10B—C10—H10C	109.5
C11—N1—C15	115.7 (3)	N1—C11—C12	124.1 (3)
C11—N1—Cu1	125.5 (2)	N1—C11—H11A	118.0
C15—N1—Cu1	118.6 (2)	C12—C11—H11A	118.0
C2—C1—H1A	109.5	C11—C12—C13	120.1 (3)
C2—C1—H1B	109.5	C11—C12—H12A	120.0
H1A—C1—H1B	109.5	C13—C12—H12A	120.0
C2—C1—H1C	109.5	C12—C13—C14	115.9 (3)
H1A—C1—H1C	109.5	C12—C13—C16	120.6 (3)
H1B—C1—H1C	109.5	C14—C13—C16	123.5 (3)
O2—C2—C3	124.7 (3)	C15—C14—C13	119.8 (3)
O2—C2—C1	114.2 (4)	C15—C14—H14A	120.1
C3—C2—C1	121.1 (4)	C13—C14—H14A	120.1
C2—C3—C4	125.7 (3)	N1—C15—C14	124.4 (3)
C2—C3—H3A	117.1	N1—C15—H15A	117.8
C4—C3—H3A	117.1	C14—C15—H15A	117.8
O1—C4—C3	124.8 (3)	C17—C16—C13	126.8 (3)
O1—C4—C5	115.3 (3)	C17—C16—H16A	116.6
C3—C4—C5	119.9 (3)	C13—C16—H16A	116.6
C4—C5—H5A	109.5	C16—C17—C18	126.7 (3)
C4—C5—H5B	109.5	C16—C17—H17A	116.6
H5A—C5—H5B	109.5	C18—C17—H17A	116.6
C4—C5—H5C	109.5	C19—C18—C20	116.5 (3)
H5A—C5—H5C	109.5	C19—C18—C17	120.3 (3)
H5B—C5—H5C	109.5	C20—C18—C17	123.2 (3)
C7—C6—H6A	109.5	C20ⁱ—C19—C18	122.2 (3)
C7—C6—H6B	109.5	C20ⁱ—C19—H19A	118.9
H6A—C6—H6B	109.5	C18—C19—H19A	118.9
C7—C6—H6C	109.5	C19ⁱ—C20—C18	121.3 (3)
H6A—C6—H6C	109.5	C19ⁱ—C20—H20A	119.3
H6B—C6—H6C	109.5	C18—C20—H20A	119.3
O4—C7—C8	125.2 (4)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O2ⁱⁱ	0.93	2.45	3.371 (4)	173
C16—H16A···O1ⁱⁱⁱ	0.93	2.52	3.333 (4)	147
C16—H16A···O3ⁱⁱⁱ	0.93	2.58	3.315 (4)	136

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

Experimental details

Crystal data
Chemical formula	[Cu₂(C₅H₇O₂)₄(C₂₀H₁₆N₂)]
M_r	807.85
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.9584 (16), 18.594 (4), 15.063 (4)
β (°)	120.97 (2)
V (Å³)	1911.2 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.17
Crystal size (mm)	0.25 × 0.21 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.759, 0.800
No. of measured, independent and observed [I > 2σ(I)] reflections	7784, 3352, 2807
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.113, 0.99
No. of reflections	3352
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.19

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O2ⁱ	0.93	2.45	3.371 (4)	172.6
C16—H16A···O1ⁱⁱ	0.93	2.52	3.333 (4)	146.8
C16—H16A···O3ⁱⁱ	0.93	2.58	3.315 (4)	136.0

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

Acknowledgements

This work was supported financially by the Doctoral Fund of Shandaong Province (No. 2007BS04046).

References

Banfi, S., Carlucci, L., Caruso, E., Ciani, G. & Proserpio, D. M. (2002). J. Chem. Soc. Dalton Trans. pp. 2714–2721. Web of Science CSD CrossRef Google Scholar
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Coe, B. J., Harries, J. L., Harris, J. A., Brunschwig, B. S., Horton, P. N. & Hursthouse, M. B. (2006). Inorg. Chem. 45, 11019–11029. Web of Science CSD CrossRef PubMed CAS Google Scholar
Liu, P. P., Cheng, A. L., Yue, Q., Liu, N., Sun, W. W. & Gao, E. Q. (2008). Cryst. Growth Des. 8, 1668–1674. Web of Science CrossRef CAS Google Scholar
Ma, Y., Cheng, A. L., Zhang, J. Y., Yue, Q. & Gao, E. Q. (2009). Cryst. Growth Des. 9, 867–873. Web of Science CSD CrossRef CAS Google Scholar
Niu, Y. Y., Hou, H. W., Wei, Y. L., Fan, Y. T., Zhu, Y., Du, C. X. & Xin, X. Q. (2001). Inorg. Chem. Commun. 4, 358–361. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2000). 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

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.