2,5-Bis[2-(4-methyl­phen­yl)ethyn­yl]benzyl methacrylate

Zhang, Z.-L.; Zhang, H.-Q.

doi:10.1107/S1600536811029631

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2168

doi:10.1107/S1600536811029631

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2,5-Bis[2-(4-methylphenyl)ethynyl]benzyl methacrylate

Zhen-Lin Zhang ^a and Hai-Quan Zhang ^a ^*

^aState Key Laboratory of Metastable Materials Science and Technology, Yanshan University, Qinhuangdao 066004, People's Republic of China
^*Correspondence e-mail: hqzhang@ysu.edu.cn

(Received 1 July 2011; accepted 22 July 2011; online 30 July 2011)

In the title bis-tolane derivative, C₂₉H₂₄O₂, the central benzene ring forms dihedral angles of 29.12 (9) and 26.46 (9)° with the other two benzene rings. The dihedral angle between two terminal benzene rings is 55.58 (8)°.

Related literature

For a related structure and the synthesis, see Zhang et al. (2010 ).

Experimental

Crystal data

C₂₉H₂₄O₂
M_r = 404.48
Monoclinic, P 2₁ /c
a = 13.479 (3) Å
b = 10.314 (2) Å
c = 18.390 (7) Å
β = 116.06 (2)°
V = 2296.7 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.14 × 0.14 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.990, T_max = 0.991
21783 measured reflections
5232 independent reflections
3322 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.162
S = 1.05
5232 reflections
283 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811029631/aa2017sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811029631/aa2017Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811029631/aa2017Isup3.cml

checkCIF report

Comment top

High birefringence liquid crystals are useful not only in conventional display devices such as STNLCDs, but also in scattering-type PDLCDs as a reflective LCD, and in spatial light modulators.They are also of interest as componens of LCDs; for example, compensation films for improving the viewing angle, reflectors and polarizers. The bistolane derivatives is very important kind of high birefringence material. We have reported the similar synthesis of the compound in previous paper (Zhang et al. 2010). Herein we present the crystal structure of the title compound (see Fig. 1). All bond lengths and angles are in the normal ranges. The three benzene rings of the title compound are not coplanar, and the dihedral angles between the side-benzene rings and the central benzene ring are 29.12 (9)° and 26.46 (9)°, respectively. The dihedral angle between two terminal benzene rings is 55.58 (8)°. The crystal packing is stabilized by Van der Waals' force.

Related literature top

For a related structure and the synthesis, see Zhang et al. (2010).

Experimental top

The title compound was prepared according to the literature (Zhang et al., 2010). Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a dichloromethane solution at room temperature.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The crystal structure of the title compound, with the atom numbering. Displacement ellipsoids of non-H atoms are drawn at the 30% probalility level.

2,5-Bis[2-(4-methylphenyl)ethynyl]benzyl 2-methylpropenoate top

Crystal data top

C₂₉H₂₄O₂	F(000) = 856
M_r = 404.48	D_x = 1.170 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5232 reflections
a = 13.479 (3) Å	θ = 3.0–27.5°
b = 10.314 (2) Å	µ = 0.07 mm⁻¹
c = 18.390 (7) Å	T = 293 K
β = 116.06 (2)°	Block, colourless
V = 2296.7 (11) Å³	0.14 × 0.14 × 0.12 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	5232 independent reflections
Radiation source: fine-focus sealed tube	3322 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −17→17
T_min = 0.990, T_max = 0.991	k = −13→13
21783 measured reflections	l = −23→23

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.090P)² + 0.0263P] where P = (F_o² + 2F_c²)/3
5232 reflections	(Δ/σ)_max = 0.026
283 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₉H₂₄O₂	V = 2296.7 (11) Å³
M_r = 404.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.479 (3) Å	µ = 0.07 mm⁻¹
b = 10.314 (2) Å	T = 293 K
c = 18.390 (7) Å	0.14 × 0.14 × 0.12 mm
β = 116.06 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	5232 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3322 reflections with I > 2σ(I)
T_min = 0.990, T_max = 0.991	R_int = 0.036
21783 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.05	Δρ_max = 0.22 e Å⁻³
5232 reflections	Δρ_min = −0.16 e Å⁻³
283 parameters

Special details top

Experimental. (See detailed section in the paper)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
O1	0.46919 (9)	0.83960 (11)	0.94444 (6)	0.0577 (3)
O2	0.31533 (11)	0.86679 (15)	0.95953 (9)	0.0855 (4)
C1	1.02239 (16)	0.9345 (3)	0.88082 (12)	0.0898 (7)
H1A	1.0037	0.9592	0.8260	0.135*
H1B	1.0873	0.8811	0.9011	0.135*
H1C	1.0364	1.0109	0.9137	0.135*
C2	0.92826 (13)	0.8602 (2)	0.88343 (9)	0.0622 (5)
C3	0.85824 (15)	0.9179 (2)	0.90984 (10)	0.0683 (5)
H3	0.8717	1.0029	0.9285	0.082*
C4	0.76866 (14)	0.8535 (2)	0.90948 (11)	0.0657 (5)
H4	0.7228	0.8952	0.9278	0.079*
C5	0.74624 (12)	0.72585 (18)	0.88170 (9)	0.0549 (4)
C6	0.81733 (13)	0.66578 (19)	0.85598 (9)	0.0584 (4)
H6	0.8044	0.5806	0.8376	0.070*
C7	0.90735 (13)	0.7320 (2)	0.85748 (10)	0.0620 (5)
H7	0.9549	0.6900	0.8408	0.074*
C8	0.65017 (13)	0.66127 (19)	0.87854 (10)	0.0607 (4)
C9	0.56739 (13)	0.61534 (18)	0.87514 (9)	0.0579 (4)
C10	0.46640 (12)	0.56551 (16)	0.87212 (9)	0.0503 (4)
C11	0.42631 (11)	0.61130 (15)	0.92603 (8)	0.0487 (4)
C12	0.32830 (12)	0.56368 (16)	0.92154 (9)	0.0518 (4)
H12	0.3025	0.5933	0.9578	0.062*
C13	0.26695 (12)	0.47142 (16)	0.86327 (9)	0.0524 (4)
C14	0.30682 (13)	0.42763 (17)	0.80977 (9)	0.0559 (4)
H14	0.2663	0.3673	0.7703	0.067*
C15	0.40513 (13)	0.47212 (17)	0.81438 (9)	0.0561 (4)
H15	0.4315	0.4401	0.7789	0.067*
C16	0.16510 (13)	0.42429 (17)	0.85986 (10)	0.0588 (4)
C17	0.08020 (13)	0.38608 (18)	0.85793 (10)	0.0609 (4)
C18	−0.02216 (13)	0.34409 (17)	0.85662 (9)	0.0545 (4)
C19	−0.03831 (14)	0.35079 (19)	0.92580 (10)	0.0648 (5)
H19	0.0188	0.3789	0.9741	0.078*
C20	−0.13764 (15)	0.3163 (2)	0.92386 (10)	0.0670 (5)
H20	−0.1464	0.3212	0.9712	0.080*
C21	−0.22507 (13)	0.27457 (17)	0.85347 (10)	0.0587 (4)
C22	−0.20792 (14)	0.2662 (2)	0.78517 (10)	0.0677 (5)
H22	−0.2651	0.2375	0.7371	0.081*
C23	−0.10906 (14)	0.2989 (2)	0.78607 (10)	0.0686 (5)
H23	−0.0998	0.2908	0.7391	0.082*
C24	−0.33470 (16)	0.2402 (2)	0.85113 (14)	0.0862 (6)
H24A	−0.3242	0.1757	0.8915	0.129*
H24B	−0.3827	0.2066	0.7986	0.129*
H24C	−0.3673	0.3162	0.8617	0.129*
C25	0.48771 (13)	0.71594 (16)	0.98580 (9)	0.0577 (4)
H25A	0.4623	0.7200	1.0276	0.069*
H25B	0.5661	0.6964	1.0114	0.069*
C26	0.37595 (13)	0.90213 (17)	0.93213 (9)	0.0570 (4)
C27	0.35602 (14)	1.01911 (17)	0.87936 (9)	0.0602 (4)
C28	0.42569 (17)	1.0441 (2)	0.84353 (11)	0.0796 (6)
H28A	0.4046	1.1243	0.8141	0.119*
H28B	0.4202	0.9749	0.8071	0.119*
H28C	0.5004	1.0505	0.8847	0.119*
C29	0.26432 (16)	1.0942 (2)	0.86929 (13)	0.0811 (6)
H29A	0.2461	1.1673	0.8364	0.097*
H29B	0.2216	1.0709	0.8955	0.097*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0557 (7)	0.0505 (7)	0.0649 (7)	−0.0080 (5)	0.0246 (5)	0.0027 (5)
O2	0.0758 (9)	0.0834 (10)	0.1147 (11)	0.0109 (7)	0.0579 (8)	0.0339 (8)
C1	0.0726 (13)	0.118 (2)	0.0835 (13)	−0.0401 (13)	0.0388 (10)	−0.0140 (12)
C2	0.0500 (9)	0.0826 (14)	0.0505 (9)	−0.0163 (9)	0.0190 (7)	−0.0017 (8)
C3	0.0696 (11)	0.0693 (13)	0.0667 (11)	−0.0188 (9)	0.0305 (9)	−0.0104 (8)
C4	0.0583 (10)	0.0750 (13)	0.0695 (10)	−0.0031 (9)	0.0334 (8)	−0.0063 (9)
C5	0.0429 (8)	0.0647 (11)	0.0548 (9)	−0.0044 (7)	0.0193 (6)	0.0062 (7)
C6	0.0491 (9)	0.0597 (11)	0.0597 (9)	−0.0011 (8)	0.0178 (7)	0.0045 (7)
C7	0.0459 (8)	0.0798 (13)	0.0599 (9)	0.0026 (8)	0.0231 (7)	0.0046 (8)
C8	0.0467 (9)	0.0706 (12)	0.0620 (10)	−0.0033 (8)	0.0211 (7)	0.0084 (8)
C9	0.0472 (9)	0.0640 (11)	0.0593 (9)	−0.0022 (8)	0.0206 (7)	0.0073 (7)
C10	0.0401 (8)	0.0523 (9)	0.0531 (8)	−0.0007 (6)	0.0154 (6)	0.0107 (7)
C11	0.0421 (8)	0.0456 (9)	0.0494 (8)	−0.0001 (6)	0.0119 (6)	0.0084 (6)
C12	0.0463 (8)	0.0525 (10)	0.0553 (8)	0.0007 (7)	0.0212 (6)	0.0069 (7)
C13	0.0424 (8)	0.0476 (9)	0.0612 (9)	−0.0024 (7)	0.0171 (6)	0.0080 (7)
C14	0.0509 (9)	0.0536 (10)	0.0554 (9)	−0.0065 (7)	0.0161 (7)	0.0009 (7)
C15	0.0523 (9)	0.0583 (10)	0.0573 (9)	−0.0020 (8)	0.0237 (7)	0.0023 (7)
C16	0.0479 (9)	0.0551 (10)	0.0690 (10)	−0.0053 (8)	0.0216 (7)	0.0021 (8)
C17	0.0507 (9)	0.0574 (11)	0.0724 (11)	−0.0068 (8)	0.0249 (8)	0.0017 (8)
C18	0.0501 (9)	0.0485 (9)	0.0641 (9)	−0.0054 (7)	0.0245 (7)	0.0030 (7)
C19	0.0566 (10)	0.0726 (13)	0.0562 (9)	−0.0077 (8)	0.0166 (7)	−0.0021 (8)
C20	0.0693 (11)	0.0791 (14)	0.0604 (10)	−0.0067 (9)	0.0358 (8)	−0.0004 (8)
C21	0.0548 (9)	0.0561 (11)	0.0700 (10)	−0.0057 (8)	0.0320 (8)	0.0037 (8)
C22	0.0567 (10)	0.0817 (14)	0.0618 (10)	−0.0236 (9)	0.0233 (8)	−0.0106 (9)
C23	0.0653 (11)	0.0865 (14)	0.0605 (10)	−0.0212 (10)	0.0335 (8)	−0.0097 (9)
C24	0.0667 (12)	0.1030 (18)	0.1036 (15)	−0.0148 (12)	0.0509 (11)	−0.0018 (12)
C25	0.0532 (9)	0.0528 (10)	0.0553 (9)	−0.0048 (7)	0.0131 (7)	0.0041 (7)
C26	0.0530 (9)	0.0551 (11)	0.0582 (9)	−0.0084 (8)	0.0201 (7)	0.0009 (7)
C27	0.0602 (10)	0.0513 (10)	0.0579 (9)	−0.0139 (8)	0.0157 (7)	0.0005 (7)
C28	0.0817 (13)	0.0797 (15)	0.0774 (12)	−0.0135 (11)	0.0350 (10)	0.0150 (10)
C29	0.0765 (13)	0.0589 (13)	0.1095 (15)	0.0069 (10)	0.0422 (11)	0.0221 (11)

Geometric parameters (Å, º) top

O1—C26	1.340 (2)	C14—H14	0.9300
O1—C25	1.449 (2)	C15—H15	0.9300
O2—C26	1.1900 (19)	C16—C17	1.196 (2)
C1—C2	1.501 (2)	C17—C18	1.436 (2)
C1—H1A	0.9600	C18—C19	1.383 (2)
C1—H1B	0.9600	C18—C23	1.392 (2)
C1—H1C	0.9600	C19—C20	1.371 (2)
C2—C3	1.372 (2)	C19—H19	0.9300
C2—C7	1.392 (3)	C20—C21	1.382 (2)
C3—C4	1.375 (2)	C20—H20	0.9300
C3—H3	0.9300	C21—C22	1.376 (2)
C4—C5	1.397 (3)	C21—C24	1.502 (2)
C4—H4	0.9300	C22—C23	1.368 (2)
C5—C6	1.387 (2)	C22—H22	0.9300
C5—C8	1.434 (2)	C23—H23	0.9300
C6—C7	1.382 (2)	C24—H24A	0.9600
C6—H6	0.9300	C24—H24B	0.9600
C7—H7	0.9300	C24—H24C	0.9600
C8—C9	1.188 (2)	C25—H25A	0.9700
C9—C10	1.433 (2)	C25—H25B	0.9700
C10—C15	1.402 (2)	C26—C27	1.497 (2)
C10—C11	1.403 (2)	C27—C28	1.388 (3)
C11—C12	1.377 (2)	C27—C29	1.400 (3)
C11—C25	1.503 (2)	C28—H28A	0.9600
C12—C13	1.400 (2)	C28—H28B	0.9600
C12—H12	0.9300	C28—H28C	0.9600
C13—C14	1.388 (2)	C29—H29A	0.9300
C13—C16	1.431 (2)	C29—H29B	0.9300
C14—C15	1.369 (2)

C26—O1—C25	116.40 (13)	C16—C17—C18	178.2 (2)
C2—C1—H1A	109.5	C19—C18—C23	117.78 (15)
C2—C1—H1B	109.5	C19—C18—C17	120.51 (15)
H1A—C1—H1B	109.5	C23—C18—C17	121.69 (15)
C2—C1—H1C	109.5	C20—C19—C18	120.65 (15)
H1A—C1—H1C	109.5	C20—C19—H19	119.7
H1B—C1—H1C	109.5	C18—C19—H19	119.7
C3—C2—C7	117.78 (16)	C19—C20—C21	121.77 (15)
C3—C2—C1	120.8 (2)	C19—C20—H20	119.1
C7—C2—C1	121.40 (18)	C21—C20—H20	119.1
C2—C3—C4	121.86 (19)	C22—C21—C20	117.29 (16)
C2—C3—H3	119.1	C22—C21—C24	121.11 (16)
C4—C3—H3	119.1	C20—C21—C24	121.60 (16)
C3—C4—C5	120.34 (17)	C23—C22—C21	121.79 (15)
C3—C4—H4	119.8	C23—C22—H22	119.1
C5—C4—H4	119.8	C21—C22—H22	119.1
C6—C5—C4	118.36 (16)	C22—C23—C18	120.68 (15)
C6—C5—C8	121.69 (17)	C22—C23—H23	119.7
C4—C5—C8	119.93 (16)	C18—C23—H23	119.7
C7—C6—C5	120.30 (18)	C21—C24—H24A	109.5
C7—C6—H6	119.9	C21—C24—H24B	109.5
C5—C6—H6	119.9	H24A—C24—H24B	109.5
C6—C7—C2	121.34 (17)	C21—C24—H24C	109.5
C6—C7—H7	119.3	H24A—C24—H24C	109.5
C2—C7—H7	119.3	H24B—C24—H24C	109.5
C9—C8—C5	175.8 (2)	O1—C25—C11	109.61 (12)
C8—C9—C10	177.4 (2)	O1—C25—H25A	109.7
C15—C10—C11	118.99 (14)	C11—C25—H25A	109.7
C15—C10—C9	120.60 (14)	O1—C25—H25B	109.7
C11—C10—C9	120.40 (15)	C11—C25—H25B	109.7
C12—C11—C10	119.64 (14)	H25A—C25—H25B	108.2
C12—C11—C25	120.35 (14)	O2—C26—O1	123.25 (16)
C10—C11—C25	119.95 (14)	O2—C26—C27	124.08 (17)
C11—C12—C13	121.12 (14)	O1—C26—C27	112.66 (14)
C11—C12—H12	119.4	C28—C27—C29	125.20 (18)
C13—C12—H12	119.4	C28—C27—C26	119.44 (17)
C14—C13—C12	118.78 (14)	C29—C27—C26	115.34 (16)
C14—C13—C16	121.41 (15)	C27—C28—H28A	109.5
C12—C13—C16	119.81 (15)	C27—C28—H28B	109.5
C15—C14—C13	120.85 (15)	H28A—C28—H28B	109.5
C15—C14—H14	119.6	C27—C28—H28C	109.5
C13—C14—H14	119.6	H28A—C28—H28C	109.5
C14—C15—C10	120.59 (15)	H28B—C28—H28C	109.5
C14—C15—H15	119.7	C27—C29—H29A	120.0
C10—C15—H15	119.7	C27—C29—H29B	120.0
C17—C16—C13	179.05 (19)	H29A—C29—H29B	120.0

C7—C2—C3—C4	−1.3 (3)	C11—C10—C15—C14	1.0 (2)
C1—C2—C3—C4	177.14 (16)	C9—C10—C15—C14	−177.85 (14)
C2—C3—C4—C5	−0.1 (3)	C23—C18—C19—C20	−1.3 (3)
C3—C4—C5—C6	1.0 (2)	C17—C18—C19—C20	177.03 (17)
C3—C4—C5—C8	−177.52 (15)	C18—C19—C20—C21	−0.3 (3)
C4—C5—C6—C7	−0.5 (2)	C19—C20—C21—C22	1.3 (3)
C8—C5—C6—C7	178.01 (13)	C19—C20—C21—C24	−178.41 (19)
C5—C6—C7—C2	−0.9 (2)	C20—C21—C22—C23	−0.7 (3)
C3—C2—C7—C6	1.9 (2)	C24—C21—C22—C23	179.1 (2)
C1—C2—C7—C6	−176.61 (15)	C21—C22—C23—C18	−1.0 (3)
C15—C10—C11—C12	0.2 (2)	C19—C18—C23—C22	2.0 (3)
C9—C10—C11—C12	179.08 (14)	C17—C18—C23—C22	−176.36 (18)
C15—C10—C11—C25	−177.08 (14)	C26—O1—C25—C11	83.10 (17)
C9—C10—C11—C25	1.8 (2)	C12—C11—C25—O1	−102.30 (16)
C10—C11—C12—C13	−0.9 (2)	C10—C11—C25—O1	75.01 (18)
C25—C11—C12—C13	176.44 (14)	C25—O1—C26—O2	7.0 (2)
C11—C12—C13—C14	0.3 (2)	C25—O1—C26—C27	−172.09 (13)
C11—C12—C13—C16	−179.67 (14)	O2—C26—C27—C28	−173.18 (18)
C12—C13—C14—C15	1.0 (2)	O1—C26—C27—C28	5.9 (2)
C16—C13—C14—C15	−179.08 (15)	O2—C26—C27—C29	5.6 (3)
C13—C14—C15—C10	−1.6 (2)	O1—C26—C27—C29	−175.33 (15)

Experimental details

Crystal data
Chemical formula	C₂₉H₂₄O₂
M_r	404.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.479 (3), 10.314 (2), 18.390 (7)
β (°)	116.06 (2)
V (Å³)	2296.7 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.14 × 0.14 × 0.12

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.990, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	21783, 5232, 3322
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.162, 1.05
No. of reflections	5232
No. of parameters	283
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.16

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Acknowledgements

The authors acknowledge financial support by the Qinhuangdao Ministry of Science and Technology of China (201001 A020) and the Hebei Province Science Foundation of China (E2010001182).

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku Corporation (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, Z. L., Zhang, L. Y., Shen, Z. H., Chen, X. F., Xing, G. Z., Fan, X. H. & Zhou, Q. F. (2010). J. Polym. Sci. Part A Polym. Chem. 48, 4627–4639. Web of Science CrossRef CAS Google Scholar