1,1′-Bicyclo­propyl-1,1′-diyl 1,1′-biphenyl-2,2′-dicarboxyl­ate

Fun, H.-K.; Quah, C.K.; Xu, K.

doi:10.1107/S160053681201851X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1630

doi:10.1107/S160053681201851X

Open

access

1,1′-Bicyclopropyl-1,1′-diyl 1,1′-biphenyl-2,2′-dicarboxylate

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah ^a § and Kai Xu ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, People's Republic of China
^*Correspondence e-mail: hkfun@usm.my

(Received 20 April 2012; accepted 25 April 2012; online 5 May 2012)

In the title compound, C₂₀H₁₆O₄, the two benzene rings form a dihedral angle of 45.70 (4)°. In the crystal, molecules are linked via C—H⋯O interactions into layers lying parallel to the bc plane.

Related literature

For the background to this study, see the first paper in this series: Fun, Quah, Wu & Zhang (2012 ). For related structures in this series, see: Fun, Lim, Quah & Wu (2012 ); Fun, Quah & Wu (2012 ). For standard bond-length data, see: Allen et al. (1987 ). For the preparation, see: Wu et al. (2012 ).

Experimental

Crystal data

C₂₀H₁₆O₄
M_r = 320.33
Monoclinic, C 2/c
a = 26.3197 (14) Å
b = 9.4184 (5) Å
c = 13.3606 (7) Å
β = 100.092 (1)°
V = 3260.7 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.43 × 0.34 × 0.17 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.962, T_max = 0.985
12233 measured reflections
5234 independent reflections
3687 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.124
S = 1.04
5234 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.24 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
C3—H3A⋯O3ⁱ	0.93	2.50	3.3410 (16)	151
C4—H4A⋯O3ⁱⁱ	0.93	2.52	3.4104 (15)	161
C10—H10A⋯O1ⁱⁱⁱ	0.93	2.57	3.496 (2)	174
Symmetry codes: (i) -x, -y+1, -z; (ii) $[x, -y+1, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+2, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681201851X/is5125sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201851X/is5125Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201851X/is5125Isup3.cml

checkCIF report

Comment top

The title compound was firstly reported as a cyclopropyl ring-fused ten-membered bislactone whose preparation could be achieved through a concise photochemical method (Wu et al., 2012). In the title compound, Fig. 1, the benzene rings (C1–C6 and C7–C12) form a dihedral angle of 45.70 (4)°. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Fun, Quah, Wu & Zhang, 2012; Fun, Lim, Quah & Wu, 2012; Fun, Quah & Wu, 2012). In the crystal (Fig. 2), molecules are linked via intermolecular C3—H3A···O3, C4—H4A···O3 and C10—H10A···O1 interactions (Table 1) into a layer parallel to the (100) plane.

Related literature top

For the background to this study, see the first paper in this series: Fun, Quah, Wu & Zhang (2012). For related structures in this series, see: Fun, Lim, Quah & Wu (2012); Fun, Quah & Wu (2012). For standard bond-length data, see: Allen et al. (1987). For the preparation, see: Wu et al. (2012).

Experimental top

The title compound was derived from the photo-induced sequential reactions of 9,10-phenanthrenedione with bicyclopropylendiene. The compound was purified by flash column chromatography with ethyl acetate/petroleum ether (1:10) as eluents. X-ray quality crystals of the title compound (m.p. 192–194 °C) were obtained from slow evaporation of an acetone and petroleum ether solution (1:10).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. A packing diagram of the title compound, viewed along the c axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

1,1'-Bicyclopropyl-1,1'-diyl 1,1'-biphenyl-2,2'-dicarboxylate top

Crystal data top

C₂₀H₁₆O₄	F(000) = 1344
M_r = 320.33	D_x = 1.305 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5289 reflections
a = 26.3197 (14) Å	θ = 2.7–31.1°
b = 9.4184 (5) Å	µ = 0.09 mm⁻¹
c = 13.3606 (7) Å	T = 296 K
β = 100.092 (1)°	Block, colourless
V = 3260.7 (3) Å³	0.43 × 0.34 × 0.17 mm
Z = 8

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	5234 independent reflections
Radiation source: fine-focus sealed tube	3687 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 31.2°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −38→30
T_min = 0.962, T_max = 0.985	k = −10→13
12233 measured reflections	l = −19→14

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) = 0.124	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0571P)² + 0.6692P] where P = (F_o² + 2F_c²)/3
5234 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₀H₁₆O₄	V = 3260.7 (3) Å³
M_r = 320.33	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 26.3197 (14) Å	µ = 0.09 mm⁻¹
b = 9.4184 (5) Å	T = 296 K
c = 13.3606 (7) Å	0.43 × 0.34 × 0.17 mm
β = 100.092 (1)°

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	5234 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3687 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.985	R_int = 0.019
12233 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.04	Δρ_max = 0.24 e Å⁻³
5234 reflections	Δρ_min = −0.19 e Å⁻³
217 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.16306 (3)	0.77985 (9)	0.06344 (6)	0.0449 (2)
O2	0.14795 (3)	0.54239 (8)	0.06055 (6)	0.03836 (18)
O3	0.09630 (3)	0.53439 (9)	0.24353 (7)	0.0472 (2)
O4	0.17759 (3)	0.62505 (9)	0.26443 (6)	0.03936 (19)
C1	−0.00465 (5)	0.77534 (15)	0.06104 (11)	0.0523 (3)
H1A	−0.0238	0.8243	0.1021	0.063*
C2	−0.02987 (5)	0.70956 (16)	−0.02684 (12)	0.0591 (4)
H2A	−0.0656	0.7157	−0.0442	0.071*
C3	−0.00266 (5)	0.63585 (15)	−0.08813 (10)	0.0549 (4)
H3A	−0.0197	0.5930	−0.1473	0.066*
C4	0.05052 (5)	0.62568 (13)	−0.06123 (9)	0.0447 (3)
H4A	0.0691	0.5737	−0.1017	0.054*
C5	0.07625 (4)	0.69263 (11)	0.02585 (8)	0.0354 (2)
C6	0.04899 (4)	0.76921 (12)	0.08875 (9)	0.0390 (2)
C7	0.07330 (4)	0.84548 (12)	0.18338 (9)	0.0412 (3)
C8	0.05919 (5)	0.98669 (15)	0.19508 (13)	0.0598 (4)
H8A	0.0359	1.0299	0.1437	0.072*
C9	0.07889 (6)	1.06313 (17)	0.28054 (15)	0.0731 (5)
H9A	0.0687	1.1568	0.2864	0.088*
C10	0.11352 (6)	1.00248 (18)	0.35741 (14)	0.0687 (5)
H10A	0.1263	1.0542	0.4157	0.082*
C11	0.12910 (5)	0.86488 (16)	0.34756 (10)	0.0521 (3)
H11A	0.1533	0.8245	0.3987	0.063*
C12	0.10904 (4)	0.78468 (13)	0.26178 (9)	0.0387 (2)
C13	0.12509 (4)	0.63393 (12)	0.25576 (7)	0.0357 (2)
C14	0.19823 (4)	0.49827 (13)	0.22704 (9)	0.0429 (3)
C15	0.19826 (4)	0.50931 (12)	0.11551 (8)	0.0384 (2)
C16	0.13365 (4)	0.68165 (12)	0.05129 (7)	0.0343 (2)
C17	0.24439 (5)	0.55872 (15)	0.07486 (10)	0.0489 (3)
H17A	0.2754	0.5802	0.1233	0.059*
H17B	0.2387	0.6182	0.0147	0.059*
C18	0.22764 (5)	0.40633 (15)	0.06318 (11)	0.0538 (3)
H18A	0.2119	0.3740	−0.0040	0.065*
H18B	0.2485	0.3360	0.1046	0.065*
C19	0.19195 (7)	0.36209 (18)	0.27970 (13)	0.0696 (4)
H19A	0.1885	0.2759	0.2393	0.084*
H19B	0.1722	0.3634	0.3346	0.084*
C20	0.24300 (6)	0.4358 (2)	0.29662 (11)	0.0694 (5)
H20A	0.2542	0.4817	0.3617	0.083*
H20B	0.2705	0.3943	0.2665	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0411 (4)	0.0398 (5)	0.0524 (5)	−0.0053 (3)	0.0041 (3)	0.0041 (4)
O2	0.0387 (4)	0.0360 (4)	0.0382 (4)	0.0023 (3)	0.0007 (3)	−0.0012 (3)
O3	0.0456 (4)	0.0456 (5)	0.0504 (5)	−0.0062 (4)	0.0084 (4)	0.0037 (4)
O4	0.0337 (4)	0.0490 (5)	0.0351 (4)	0.0054 (3)	0.0052 (3)	−0.0027 (3)
C1	0.0362 (6)	0.0546 (8)	0.0642 (8)	0.0055 (5)	0.0043 (5)	0.0055 (6)
C2	0.0369 (6)	0.0623 (9)	0.0709 (9)	−0.0037 (6)	−0.0102 (6)	0.0134 (7)
C3	0.0519 (7)	0.0561 (8)	0.0486 (7)	−0.0126 (6)	−0.0135 (6)	0.0087 (6)
C4	0.0500 (6)	0.0437 (7)	0.0370 (5)	−0.0049 (5)	−0.0017 (5)	0.0032 (5)
C5	0.0360 (5)	0.0331 (5)	0.0351 (5)	−0.0022 (4)	0.0005 (4)	0.0064 (4)
C6	0.0351 (5)	0.0359 (6)	0.0442 (6)	0.0029 (4)	0.0020 (4)	0.0045 (5)
C7	0.0367 (5)	0.0373 (6)	0.0502 (6)	0.0015 (4)	0.0091 (5)	−0.0051 (5)
C8	0.0554 (7)	0.0439 (7)	0.0795 (10)	0.0075 (6)	0.0101 (7)	−0.0091 (7)
C9	0.0669 (9)	0.0481 (8)	0.1057 (13)	0.0041 (7)	0.0188 (9)	−0.0300 (9)
C10	0.0543 (8)	0.0691 (10)	0.0843 (11)	−0.0093 (7)	0.0165 (7)	−0.0430 (9)
C11	0.0368 (6)	0.0655 (9)	0.0539 (7)	−0.0037 (5)	0.0077 (5)	−0.0234 (6)
C12	0.0305 (5)	0.0437 (6)	0.0430 (6)	−0.0016 (4)	0.0099 (4)	−0.0089 (5)
C13	0.0352 (5)	0.0447 (6)	0.0273 (4)	0.0002 (4)	0.0059 (4)	0.0003 (4)
C14	0.0445 (6)	0.0479 (7)	0.0364 (5)	0.0152 (5)	0.0072 (4)	0.0055 (5)
C15	0.0379 (5)	0.0409 (6)	0.0353 (5)	0.0081 (4)	0.0036 (4)	−0.0031 (4)
C16	0.0380 (5)	0.0364 (6)	0.0280 (4)	0.0007 (4)	0.0046 (4)	0.0027 (4)
C17	0.0420 (6)	0.0606 (8)	0.0451 (6)	0.0037 (5)	0.0105 (5)	−0.0069 (6)
C18	0.0544 (7)	0.0559 (8)	0.0505 (7)	0.0153 (6)	0.0079 (5)	−0.0132 (6)
C19	0.0852 (11)	0.0595 (9)	0.0680 (10)	0.0263 (8)	0.0240 (8)	0.0266 (8)
C20	0.0645 (9)	0.0966 (12)	0.0456 (7)	0.0407 (9)	0.0053 (6)	0.0153 (8)

Geometric parameters (Å, º) top

O1—C16	1.1986 (13)	C9—C10	1.373 (2)
O2—C16	1.3641 (13)	C9—H9A	0.9300
O2—C15	1.4314 (12)	C10—C11	1.373 (2)
O3—C13	1.1984 (13)	C10—H10A	0.9300
O4—C13	1.3688 (12)	C11—C12	1.3967 (16)
O4—C14	1.4372 (14)	C11—H11A	0.9300
C1—C2	1.389 (2)	C12—C13	1.4875 (16)
C1—C6	1.3966 (15)	C14—C19	1.486 (2)
C1—H1A	0.9300	C14—C20	1.4883 (16)
C2—C3	1.368 (2)	C14—C15	1.4939 (16)
C2—H2A	0.9300	C15—C18	1.4889 (17)
C3—C4	1.3859 (17)	C15—C17	1.4889 (17)
C3—H3A	0.9300	C17—C18	1.502 (2)
C4—C5	1.3906 (15)	C17—H17A	0.9700
C4—H4A	0.9300	C17—H17B	0.9700
C5—C6	1.3972 (17)	C18—H18A	0.9700
C5—C16	1.4930 (14)	C18—H18B	0.9700
C6—C7	1.4967 (16)	C19—C20	1.494 (3)
C7—C8	1.3970 (18)	C19—H19A	0.9700
C7—C12	1.4017 (16)	C19—H19B	0.9700
C8—C9	1.372 (2)	C20—H20A	0.9700
C8—H8A	0.9300	C20—H20B	0.9700

C16—O2—C15	118.13 (8)	O4—C13—C12	110.23 (9)
C13—O4—C14	117.31 (9)	O4—C14—C19	118.18 (11)
C2—C1—C6	121.11 (13)	O4—C14—C20	114.67 (11)
C2—C1—H1A	119.4	C19—C14—C20	60.30 (11)
C6—C1—H1A	119.4	O4—C14—C15	110.81 (9)
C3—C2—C1	120.63 (12)	C19—C14—C15	123.50 (12)
C3—C2—H2A	119.7	C20—C14—C15	120.79 (11)
C1—C2—H2A	119.7	O2—C15—C18	114.25 (9)
C2—C3—C4	119.39 (12)	O2—C15—C17	119.02 (10)
C2—C3—H3A	120.3	C18—C15—C17	60.56 (9)
C4—C3—H3A	120.3	O2—C15—C14	111.39 (9)
C3—C4—C5	120.48 (13)	C18—C15—C14	120.94 (10)
C3—C4—H4A	119.8	C17—C15—C14	121.91 (10)
C5—C4—H4A	119.8	O1—C16—O2	124.63 (10)
C4—C5—C6	120.75 (10)	O1—C16—C5	125.52 (10)
C4—C5—C16	118.95 (11)	O2—C16—C5	109.84 (9)
C6—C5—C16	120.30 (9)	C15—C17—C18	59.72 (9)
C1—C6—C5	117.62 (11)	C15—C17—H17A	117.8
C1—C6—C7	117.82 (11)	C18—C17—H17A	117.8
C5—C6—C7	124.57 (9)	C15—C17—H17B	117.8
C8—C7—C12	117.51 (11)	C18—C17—H17B	117.8
C8—C7—C6	117.96 (11)	H17A—C17—H17B	114.9
C12—C7—C6	124.52 (10)	C15—C18—C17	59.72 (8)
C9—C8—C7	121.57 (14)	C15—C18—H18A	117.8
C9—C8—H8A	119.2	C17—C18—H18A	117.8
C7—C8—H8A	119.2	C15—C18—H18B	117.8
C8—C9—C10	120.58 (14)	C17—C18—H18B	117.8
C8—C9—H9A	119.7	H18A—C18—H18B	114.9
C10—C9—H9A	119.7	C14—C19—C20	59.92 (10)
C11—C10—C9	119.44 (13)	C14—C19—H19A	117.8
C11—C10—H10A	120.3	C20—C19—H19A	117.8
C9—C10—H10A	120.3	C14—C19—H19B	117.8
C10—C11—C12	120.87 (13)	C20—C19—H19B	117.8
C10—C11—H11A	119.6	H19A—C19—H19B	114.9
C12—C11—H11A	119.6	C14—C20—C19	59.78 (9)
C11—C12—C7	120.00 (11)	C14—C20—H20A	117.8
C11—C12—C13	119.38 (11)	C19—C20—H20A	117.8
C7—C12—C13	120.61 (10)	C14—C20—H20B	117.8
O3—C13—O4	124.64 (11)	C19—C20—H20B	117.8
O3—C13—C12	125.13 (10)	H20A—C20—H20B	114.9

C6—C1—C2—C3	0.6 (2)	C7—C12—C13—O4	123.65 (11)
C1—C2—C3—C4	0.8 (2)	C13—O4—C14—C19	−66.02 (14)
C2—C3—C4—C5	−1.62 (19)	C13—O4—C14—C20	−134.16 (12)
C3—C4—C5—C6	1.13 (17)	C13—O4—C14—C15	84.84 (12)
C3—C4—C5—C16	−178.81 (11)	C16—O2—C15—C18	−132.94 (11)
C2—C1—C6—C5	−1.04 (19)	C16—O2—C15—C17	−64.44 (13)
C2—C1—C6—C7	178.72 (12)	C16—O2—C15—C14	85.60 (12)
C4—C5—C6—C1	0.20 (17)	O4—C14—C15—O2	−54.61 (13)
C16—C5—C6—C1	−179.86 (11)	C19—C14—C15—O2	94.42 (14)
C4—C5—C6—C7	−179.54 (11)	C20—C14—C15—O2	167.13 (12)
C16—C5—C6—C7	0.40 (17)	O4—C14—C15—C18	166.88 (11)
C1—C6—C7—C8	−49.77 (17)	C19—C14—C15—C18	−44.10 (18)
C5—C6—C7—C8	129.97 (13)	C20—C14—C15—C18	28.61 (19)
C1—C6—C7—C12	129.69 (13)	O4—C14—C15—C17	94.44 (13)
C5—C6—C7—C12	−50.56 (18)	C19—C14—C15—C17	−116.54 (15)
C12—C7—C8—C9	−0.9 (2)	C20—C14—C15—C17	−43.82 (18)
C6—C7—C8—C9	178.62 (14)	C15—O2—C16—O1	18.83 (16)
C7—C8—C9—C10	0.3 (3)	C15—O2—C16—C5	−160.13 (9)
C8—C9—C10—C11	1.1 (3)	C4—C5—C16—O1	123.22 (13)
C9—C10—C11—C12	−1.9 (2)	C6—C5—C16—O1	−56.72 (16)
C10—C11—C12—C7	1.3 (2)	C4—C5—C16—O2	−57.83 (13)
C10—C11—C12—C13	−177.34 (13)	C6—C5—C16—O2	122.23 (11)
C8—C7—C12—C11	0.07 (18)	O2—C15—C17—C18	−103.08 (11)
C6—C7—C12—C11	−179.39 (11)	C14—C15—C17—C18	110.12 (12)
C8—C7—C12—C13	178.70 (12)	O2—C15—C18—C17	110.90 (11)
C6—C7—C12—C13	−0.76 (18)	C14—C15—C18—C17	−111.67 (13)
C14—O4—C13—O3	19.37 (15)	O4—C14—C19—C20	−103.86 (13)
C14—O4—C13—C12	−159.59 (9)	C15—C14—C19—C20	109.22 (14)
C11—C12—C13—O3	123.34 (13)	O4—C14—C20—C19	109.65 (13)
C7—C12—C13—O3	−55.30 (16)	C15—C14—C20—C19	−113.56 (15)
C11—C12—C13—O4	−57.71 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O3ⁱ	0.93	2.50	3.3410 (16)	151
C4—H4A···O3ⁱⁱ	0.93	2.52	3.4104 (15)	161
C10—H10A···O1ⁱⁱⁱ	0.93	2.57	3.496 (2)	174

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆O₄
M_r	320.33
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	26.3197 (14), 9.4184 (5), 13.3606 (7)
β (°)	100.092 (1)
V (Å³)	3260.7 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.43 × 0.34 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.962, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	12233, 5234, 3687
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.729

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.124, 1.04
No. of reflections	5234
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.19

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O3ⁱ	0.93	2.50	3.3410 (16)	151
C4—H4A···O3ⁱⁱ	0.93	2.52	3.4104 (15)	161
C10—H10A···O1ⁱⁱⁱ	0.93	2.57	3.496 (2)	174

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160). Financial support from the National Natural Science Foundation of China (20972067) is acknowledged.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K., Lim, M. Y., Quah, C. K. & Wu, D. (2012). Acta Cryst. E68, o1629. CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Quah, C. K. & Wu, D. (2012). Acta Cryst. E68, o1628. CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Quah, C. K., Wu, D. & Zhang, Y. (2012). Acta Cryst. E68, o1627. CSD CrossRef IUCr Journals 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
Wu, D., Wang, L., Xu, K., Song, J., Fun, H.-K., Xu, J. & Zhang, Y. (2012). Chem. Commun. 48, 1168–1170. Web of Science CSD CrossRef CAS Google Scholar