Tris(1,10-phenanthroline)cobalt(II) bis­(trichloro­acetate)

Li, L.-M.; Li, Y.-F.; Liu, L.; Zhang, Z.-H.

doi:10.1107/S160053681102410X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m973

doi:10.1107/S160053681102410X

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Tris(1,10-phenanthroline)cobalt(II) bis(trichloroacetate)

Li-Min Li,^a ^* Yu-Feng Li,^a Li Liu ^a and Zeng-Hui Zhang ^b

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and ^bDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 15 May 2011; accepted 20 June 2011; online 25 June 2011)

In the title complex, [Co(C₁₂H₈N₂)₃](C₂Cl₃O₂)₂, the Co^II ion lies on a twofold rotation axis and is coordinated by six N atoms from three bis-chelating 1,10-phenanthroline ligands in a distorted octahedral environment. The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For background to metal-organic framework coordination polymers, see: Chen et al. (2001 ); Fang et al. (2005 ). For a related structure, see: Harding et al. (2008 ).

Experimental

Crystal data

[Co(C₁₂H₈N₂)₃](C₂Cl₃O₂)₂
M_r = 924.28
Monoclinic, C 2/c
a = 18.367 (4) Å
b = 10.753 (2) Å
c = 19.020 (4) Å
β = 100.94 (3)°
V = 3688.2 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.95 mm⁻¹
T = 293 K
0.26 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.837, T_max = 0.923
17083 measured reflections
4215 independent reflections
3364 reflections with I > 2σ(I)
R_int = 0.092

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.142
S = 0.89
4215 reflections
258 parameters
H-atom parameters constrained
Δρ_max = 0.81 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1ⁱ	0.93	2.54	3.401 (3)	154
C10—H10A⋯O2ⁱⁱ	0.93	2.35	3.120 (3)	140
C13—H13A⋯O1ⁱⁱⁱ	0.93	2.28	3.004 (3)	134
C14—H14A⋯O1^iv	0.93	2.60	3.455 (3)	154
C15—H15A⋯O2^iv	0.93	2.56	3.266 (3)	133
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) -x, -y, -z; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x, -y+1, z+{\script{1\over 2}}]$ .

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/S160053681102410X/lh5253sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681102410X/lh5253Isup2.hkl

checkCIF report

Comment top

Metal-organic framework coordination polymers have attracted tremendous attention because of their molecular topologies and their potentially useful ionexchange, adsorption, catalytic and magnetic properties (Chen et al., 2001; Fang et al.,2005). As part of our search for new complexes of this type, we synthesized the title compound and report its crystal structure herein.

The molecular structure of the title complex is shown in Fig. 1. The Co^II ion lies on a twofold rotation axis and is coordinated by six N atoms of three bis-chelating 1,10-phenanthroline ligands in a distorted octahedral environment. The Co—N bond lengths are in agreement with those reported for a related complex (Harding et al., 2008). The crystal structure is stabilized by weak intermolecular C—H···O hydrogen bonds.

Related literature top

For background to metal-organic framework coordination polymers, see: Chen et al. (2001); Fang et al. (2005). For a related structure, see: Harding et al. (2008).

Experimental top

The title compound was obtained by adding 1,10-phenanthroline (3 mmol) dropwise to a solution of cobalt(II) trichloroacetic acid (1 mmol) in ethanol (20 ml). The solution was stirred for 1 h at room temperature. After a few days block-shaped crystals were formed from the yellow solution.

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 showing 30% probability displacement ellipsoids (symmetry code: (A) -x, y, -z + 1/2). Only the unique anion is shown.

Tris(1,10-phenanthroline)cobalt(II) bis(trichloroacetate) top

Crystal data top

[Co(C₁₂H₈N₂)₃](C₂Cl₃O₂)₂	F(000) = 1868
M_r = 924.28	D_x = 1.665 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3364 reflections
a = 18.367 (4) Å	θ = 3.3–27.5°
b = 10.753 (2) Å	µ = 0.95 mm⁻¹
c = 19.020 (4) Å	T = 293 K
β = 100.94 (3)°	Block, yellow
V = 3688.2 (13) Å³	0.26 × 0.20 × 0.12 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	4215 independent reflections
Radiation source: fine-focus sealed tube	3364 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.092
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 3.3°
ϕ and ω scans	h = −23→23
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
T_min = 0.837, T_max = 0.923	l = −22→24
17083 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 0.89	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
4215 reflections	(Δ/σ)_max < 0.001
258 parameters	Δρ_max = 0.81 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Co(C₁₂H₈N₂)₃](C₂Cl₃O₂)₂	V = 3688.2 (13) Å³
M_r = 924.28	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 18.367 (4) Å	µ = 0.95 mm⁻¹
b = 10.753 (2) Å	T = 293 K
c = 19.020 (4) Å	0.26 × 0.20 × 0.12 mm
β = 100.94 (3)°

Data collection top

Bruker SMART CCD diffractometer	4215 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3364 reflections with I > 2σ(I)
T_min = 0.837, T_max = 0.923	R_int = 0.092
17083 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.142	H-atom parameters constrained
S = 0.89	Δρ_max = 0.81 e Å⁻³
4215 reflections	Δρ_min = −0.45 e Å⁻³
258 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
Co1	0.0000	0.08051 (4)	0.2500	0.01371 (15)
N1	0.08711 (11)	0.05924 (18)	0.19106 (10)	0.0166 (4)
N2	−0.04713 (11)	−0.05011 (17)	0.16840 (10)	0.0171 (4)
N3	0.05538 (10)	0.23619 (17)	0.30672 (9)	0.0139 (4)
C1	0.15367 (13)	0.1115 (2)	0.20262 (13)	0.0219 (5)
H1A	0.1671	0.1614	0.2429	0.026*
C2	0.20463 (14)	0.0959 (2)	0.15766 (14)	0.0244 (5)
H2A	0.2511	0.1330	0.1686	0.029*
C3	0.18537 (14)	0.0252 (2)	0.09727 (13)	0.0230 (5)
H3A	0.2174	0.0175	0.0651	0.028*
C4	0.11654 (13)	−0.0354 (2)	0.08449 (12)	0.0199 (5)
C5	0.06900 (12)	−0.0155 (2)	0.13273 (11)	0.0163 (4)
C6	−0.00237 (13)	−0.0750 (2)	0.12096 (12)	0.0158 (4)
C7	−0.02363 (13)	−0.1525 (2)	0.06160 (12)	0.0209 (5)
C8	0.02684 (15)	−0.1718 (2)	0.01384 (13)	0.0264 (5)
H8A	0.0134	−0.2243	−0.0253	0.032*
C9	0.09337 (15)	−0.1153 (3)	0.02451 (13)	0.0260 (5)
H9A	0.1248	−0.1286	−0.0077	0.031*
C10	−0.09434 (13)	−0.2060 (2)	0.05130 (13)	0.0234 (5)
H10A	−0.1101	−0.2593	0.0129	0.028*
C11	−0.13996 (13)	−0.1790 (2)	0.09837 (14)	0.0239 (5)
H11A	−0.1876	−0.2120	0.0918	0.029*
C12	−0.11401 (13)	−0.1013 (2)	0.15618 (13)	0.0209 (5)
H12A	−0.1453	−0.0843	0.1881	0.025*
C13	0.11155 (12)	0.2351 (2)	0.36144 (12)	0.0179 (5)
H13A	0.1308	0.1586	0.3786	0.022*
C14	0.14369 (13)	0.3426 (2)	0.39495 (12)	0.0208 (5)
H14A	0.1832	0.3371	0.4335	0.025*
C15	0.11645 (13)	0.4560 (2)	0.37044 (12)	0.0217 (5)
H15A	0.1360	0.5285	0.3931	0.026*
C16	0.05858 (12)	0.4615 (2)	0.31049 (12)	0.0173 (5)
C17	0.02949 (12)	0.3489 (2)	0.28041 (11)	0.0149 (4)
C18	0.02748 (14)	0.5754 (2)	0.27896 (14)	0.0225 (5)
H18A	0.0457	0.6508	0.2989	0.027*
Cl1	0.18800 (5)	0.41813 (7)	0.18548 (4)	0.0414 (2)
Cl2	0.06670 (4)	0.51120 (9)	0.07856 (5)	0.0454 (2)
Cl3	0.17181 (4)	0.67933 (6)	0.15928 (4)	0.0368 (2)
O1	0.25779 (11)	0.59450 (19)	0.05738 (11)	0.0341 (5)
O2	0.19590 (11)	0.41976 (17)	0.02240 (10)	0.0292 (4)
C20	0.16126 (14)	0.5325 (2)	0.11741 (13)	0.0245 (5)
C19	0.21116 (12)	0.5134 (2)	0.05881 (12)	0.0215 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0146 (2)	0.0140 (2)	0.0126 (2)	0.000	0.00274 (17)	0.000
N1	0.0169 (9)	0.0178 (9)	0.0155 (9)	−0.0009 (7)	0.0041 (8)	−0.0021 (7)
N2	0.0195 (9)	0.0134 (9)	0.0174 (9)	0.0003 (7)	0.0010 (8)	−0.0002 (7)
N3	0.0144 (8)	0.0157 (9)	0.0111 (8)	−0.0005 (7)	0.0013 (7)	−0.0017 (6)
C1	0.0217 (12)	0.0256 (12)	0.0189 (12)	−0.0045 (10)	0.0054 (10)	−0.0047 (9)
C2	0.0184 (11)	0.0283 (13)	0.0276 (13)	−0.0051 (10)	0.0071 (10)	−0.0035 (10)
C3	0.0237 (12)	0.0279 (13)	0.0198 (12)	0.0033 (10)	0.0101 (10)	0.0014 (9)
C4	0.0246 (12)	0.0207 (11)	0.0153 (11)	0.0041 (9)	0.0060 (9)	0.0025 (8)
C5	0.0186 (10)	0.0160 (10)	0.0140 (10)	0.0028 (9)	0.0025 (9)	0.0009 (8)
C6	0.0180 (10)	0.0154 (10)	0.0132 (10)	0.0015 (8)	0.0009 (9)	0.0018 (8)
C7	0.0260 (12)	0.0181 (11)	0.0164 (11)	0.0019 (9)	−0.0018 (10)	−0.0018 (8)
C8	0.0363 (14)	0.0254 (13)	0.0174 (12)	0.0043 (11)	0.0047 (11)	−0.0051 (9)
C9	0.0323 (13)	0.0300 (13)	0.0179 (12)	0.0043 (11)	0.0104 (11)	−0.0027 (10)
C10	0.0255 (11)	0.0203 (11)	0.0204 (12)	−0.0014 (10)	−0.0059 (10)	−0.0024 (9)
C11	0.0206 (11)	0.0164 (12)	0.0318 (14)	−0.0016 (9)	−0.0022 (10)	0.0017 (9)
C12	0.0176 (11)	0.0179 (11)	0.0264 (13)	−0.0005 (9)	0.0023 (10)	0.0006 (9)
C13	0.0184 (10)	0.0208 (11)	0.0138 (11)	0.0038 (9)	0.0009 (9)	−0.0003 (8)
C14	0.0160 (10)	0.0305 (13)	0.0135 (10)	−0.0014 (9)	−0.0033 (9)	−0.0025 (9)
C15	0.0248 (12)	0.0210 (12)	0.0191 (11)	−0.0033 (10)	0.0041 (10)	−0.0047 (9)
C16	0.0149 (10)	0.0187 (11)	0.0184 (11)	−0.0006 (9)	0.0037 (9)	−0.0009 (8)
C17	0.0147 (10)	0.0169 (11)	0.0140 (10)	0.0009 (8)	0.0053 (9)	−0.0002 (8)
C18	0.0270 (12)	0.0141 (11)	0.0247 (12)	−0.0015 (9)	0.0007 (10)	−0.0019 (9)
Cl1	0.0599 (5)	0.0325 (4)	0.0382 (4)	0.0076 (3)	0.0255 (4)	0.0144 (3)
Cl2	0.0190 (3)	0.0604 (5)	0.0581 (5)	−0.0049 (3)	0.0110 (3)	−0.0155 (4)
Cl3	0.0469 (4)	0.0273 (4)	0.0337 (4)	0.0072 (3)	0.0007 (3)	−0.0071 (3)
O1	0.0268 (10)	0.0393 (12)	0.0367 (11)	−0.0156 (8)	0.0074 (9)	−0.0009 (8)
O2	0.0271 (10)	0.0328 (10)	0.0277 (10)	−0.0036 (8)	0.0049 (8)	−0.0083 (7)
C20	0.0221 (11)	0.0250 (13)	0.0258 (13)	−0.0022 (10)	0.0033 (10)	−0.0008 (9)
C19	0.0148 (10)	0.0309 (13)	0.0176 (11)	−0.0020 (9)	0.0001 (9)	0.0034 (9)

Geometric parameters (Å, º) top

Co1—N1ⁱ	2.1330 (19)	C8—H8A	0.9300
Co1—N1	2.1330 (19)	C9—H9A	0.9300
Co1—N3	2.1411 (18)	C10—C11	1.368 (4)
Co1—N3ⁱ	2.1411 (18)	C10—H10A	0.9300
Co1—N2	2.1497 (19)	C11—C12	1.391 (3)
Co1—N2ⁱ	2.1497 (19)	C11—H11A	0.9300
N1—C1	1.325 (3)	C12—H12A	0.9300
N1—C5	1.359 (3)	C13—C14	1.396 (3)
N2—C12	1.326 (3)	C13—H13A	0.9300
N2—C6	1.358 (3)	C14—C15	1.366 (3)
N3—C13	1.319 (3)	C14—H14A	0.9300
N3—C17	1.362 (3)	C15—C16	1.405 (3)
C1—C2	1.393 (3)	C15—H15A	0.9300
C1—H1A	0.9300	C16—C17	1.401 (3)
C2—C3	1.366 (4)	C16—C18	1.434 (3)
C2—H2A	0.9300	C17—C17ⁱ	1.427 (4)
C3—C4	1.402 (3)	C18—C18ⁱ	1.345 (5)
C3—H3A	0.9300	C18—H18A	0.9300
C4—C5	1.398 (3)	Cl1—C20	1.786 (3)
C4—C9	1.428 (3)	Cl2—C20	1.769 (3)
C5—C6	1.438 (3)	Cl3—C20	1.762 (3)
C6—C7	1.398 (3)	O1—C19	1.226 (3)
C7—C10	1.400 (3)	O2—C19	1.224 (3)
C7—C8	1.431 (3)	C20—C19	1.585 (3)
C8—C9	1.345 (4)

N1ⁱ—Co1—N1	167.69 (10)	C10—C7—C8	123.2 (2)
N1ⁱ—Co1—N3	98.69 (7)	C9—C8—C7	121.2 (2)
N1—Co1—N3	90.95 (7)	C9—C8—H8A	119.4
N1ⁱ—Co1—N3ⁱ	90.95 (7)	C7—C8—H8A	119.4
N1—Co1—N3ⁱ	98.69 (7)	C8—C9—C4	121.1 (2)
N3—Co1—N3ⁱ	77.14 (10)	C8—C9—H9A	119.4
N1ⁱ—Co1—N2	94.01 (8)	C4—C9—H9A	119.4
N1—Co1—N2	77.87 (7)	C11—C10—C7	119.2 (2)
N3—Co1—N2	164.22 (7)	C11—C10—H10A	120.4
N3ⁱ—Co1—N2	93.40 (7)	C7—C10—H10A	120.4
N1ⁱ—Co1—N2ⁱ	77.87 (7)	C10—C11—C12	119.0 (2)
N1—Co1—N2ⁱ	94.01 (8)	C10—C11—H11A	120.5
N3—Co1—N2ⁱ	93.40 (7)	C12—C11—H11A	120.5
N3ⁱ—Co1—N2ⁱ	164.22 (7)	N2—C12—C11	123.7 (2)
N2—Co1—N2ⁱ	98.40 (10)	N2—C12—H12A	118.1
C1—N1—C5	117.5 (2)	C11—C12—H12A	118.1
C1—N1—Co1	128.87 (16)	N3—C13—C14	123.5 (2)
C5—N1—Co1	113.61 (15)	N3—C13—H13A	118.2
C12—N2—C6	117.3 (2)	C14—C13—H13A	118.2
C12—N2—Co1	129.10 (17)	C15—C14—C13	119.2 (2)
C6—N2—Co1	113.39 (15)	C15—C14—H14A	120.4
C13—N3—C17	117.65 (19)	C13—C14—H14A	120.4
C13—N3—Co1	128.03 (16)	C14—C15—C16	119.1 (2)
C17—N3—Co1	114.28 (14)	C14—C15—H15A	120.4
N1—C1—C2	123.6 (2)	C16—C15—H15A	120.4
N1—C1—H1A	118.2	C17—C16—C15	117.8 (2)
C2—C1—H1A	118.2	C17—C16—C18	118.5 (2)
C3—C2—C1	119.1 (2)	C15—C16—C18	123.8 (2)
C3—C2—H2A	120.4	N3—C17—C16	122.7 (2)
C1—C2—H2A	120.4	N3—C17—C17ⁱ	117.15 (12)
C2—C3—C4	119.0 (2)	C16—C17—C17ⁱ	120.20 (13)
C2—C3—H3A	120.5	C18ⁱ—C18—C16	121.32 (14)
C4—C3—H3A	120.5	C18ⁱ—C18—H18A	119.3
C5—C4—C3	118.0 (2)	C16—C18—H18A	119.3
C5—C4—C9	119.2 (2)	C19—C20—Cl3	113.91 (17)
C3—C4—C9	122.7 (2)	C19—C20—Cl2	110.03 (16)
N1—C5—C4	122.6 (2)	Cl3—C20—Cl2	108.66 (14)
N1—C5—C6	117.7 (2)	C19—C20—Cl1	107.71 (17)
C4—C5—C6	119.6 (2)	Cl3—C20—Cl1	107.33 (13)
N2—C6—C7	122.9 (2)	Cl2—C20—Cl1	109.08 (14)
N2—C6—C5	117.3 (2)	O2—C19—O1	131.2 (2)
C7—C6—C5	119.9 (2)	O2—C19—C20	113.8 (2)
C6—C7—C10	117.9 (2)	O1—C19—C20	115.0 (2)
C6—C7—C8	118.9 (2)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1ⁱⁱ	0.93	2.54	3.401 (3)	154
C10—H10A···O2ⁱⁱⁱ	0.93	2.35	3.120 (3)	140
C13—H13A···O1^iv	0.93	2.28	3.004 (3)	134
C14—H14A···O1^v	0.93	2.60	3.455 (3)	154
C15—H15A···O2^v	0.93	2.56	3.266 (3)	133

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

Experimental details

Crystal data
Chemical formula	[Co(C₁₂H₈N₂)₃](C₂Cl₃O₂)₂
M_r	924.28
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	18.367 (4), 10.753 (2), 19.020 (4)
β (°)	100.94 (3)
V (Å³)	3688.2 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.95
Crystal size (mm)	0.26 × 0.20 × 0.12

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.837, 0.923
No. of measured, independent and observed [I > 2σ(I)] reflections	17083, 4215, 3364
R_int	0.092
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.142, 0.89
No. of reflections	4215
No. of parameters	258
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.81, −0.45

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
C9—H9A···O1ⁱ	0.93	2.54	3.401 (3)	154
C10—H10A···O2ⁱⁱ	0.93	2.35	3.120 (3)	140
C13—H13A···O1ⁱⁱⁱ	0.93	2.28	3.004 (3)	134
C14—H14A···O1^iv	0.93	2.60	3.455 (3)	154
C15—H15A···O2^iv	0.93	2.56	3.266 (3)	133

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

Acknowledgements

The authors would like to thank the Natural Science Foundation of Shandong Province (No. Y2008B30).

References

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