1-(2-Bromophenyl)ethane-1,2-diyl 1,1′-biphenyl-2,2′-dicarboxylate

Fun, H.-K.; Quah, C.K.; Wu, D.

doi:10.1107/S1600536812018053

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1552

doi:10.1107/S1600536812018053

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1-(2-Bromophenyl)ethane-1,2-diyl 1,1′-biphenyl-2,2′-dicarboxylate

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah ^a § and Dongdong Wu ^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 23 April 2012; online 28 April 2012)

In the title compound, C₂₂H₁₅BrO₄, the bromobenzene ring is inclined at dihedral angles of 23.87 (11) and 52.37 (11)° with respect to the planes of the two benzene rings. The two benzene rings of the biphenyl unit form a dihedral angle of 49.08 (11)°. In the crystal, molecules are linked into [100] chains by C—H⋯O hydrogen bonds.

Related literature

For a related structure, references to other similar structures and chemical and biological background, see: Fun et al. (2012). For the preparation, see: Wu et al. (2012).

Experimental

Crystal data

C₂₂H₁₅BrO₄
M_r = 423.25
Monoclinic, P 2₁ /c
a = 8.0436 (9) Å
b = 21.775 (2) Å
c = 12.8809 (11) Å
β = 125.613 (5)°
V = 1834.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.27 mm⁻¹
T = 296 K
0.41 × 0.23 × 0.17 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.456, T_max = 0.702
17934 measured reflections
5372 independent reflections
3377 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.102
S = 1.02
5372 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21A⋯O1ⁱ	0.93	2.44	3.321 (3)	158
Symmetry code: (i) x-1, y, z.

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/S1600536812018053/hb6749sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812018053/hb6749Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812018053/hb6749Isup3.cml

checkCIF report

Comment top

As part of our ongoing synthetic and structural studies of bis-lactones containing a biaryl motif (Wu et al., 2012; Fun et al. 2012), we now report the structure of the title compound, (I).

In the title compound, Fig. 1, the bromo attached phenyl ring (C17-C22) inclines at dihedral angles of 23.87 (11) and 52.37 (11)° with the two benzene rings (C1-C6 and C7-C12), respectively. The two benzene rings form a dihedral angle of 49.08 (11)°. Bond lengths and angles are comparable to a related structure (Fun et al., 2012).

In the crystal (Fig. 2), molecules are linked into one-dimensional chains propagating along the [100] direction via C21–H21A···O1 hydrogen bonds (Table 1).

Related literature top

For a related structure, references to other similar structures and chemical and biological background, see: Fun et al. (2012). For the preparation, see: Wu et al. (2012).

Experimental top

The title compound was the major diastereoisomer of the sequential photoreaction products of 9,10-phenanthrenedione with 1-bromo-2-vinylbenzene. The compound was purified by flash column chromatography with ethyl acetate/petroleum ether (1:9) as eluents. Colourless blocks 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. The crystal structure of the title compound, viewed along the c axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

1-(2-Bromophenyl)ethane-1,2-diyl 1,1'-biphenyl-2,2'-dicarboxylate top

Crystal data top

C₂₂H₁₅BrO₄	F(000) = 856
M_r = 423.25	D_x = 1.533 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3936 reflections
a = 8.0436 (9) Å	θ = 2.7–25.1°
b = 21.775 (2) Å	µ = 2.27 mm⁻¹
c = 12.8809 (11) Å	T = 296 K
β = 125.613 (5)°	Block, colourless
V = 1834.1 (3) Å³	0.41 × 0.23 × 0.17 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	5372 independent reflections
Radiation source: fine-focus sealed tube	3377 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 30.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.456, T_max = 0.702	k = −30→26
17934 measured reflections	l = −18→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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0405P)² + 0.5554P] where P = (F_o² + 2F_c²)/3
5372 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

C₂₂H₁₅BrO₄	V = 1834.1 (3) Å³
M_r = 423.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.0436 (9) Å	µ = 2.27 mm⁻¹
b = 21.775 (2) Å	T = 296 K
c = 12.8809 (11) Å	0.41 × 0.23 × 0.17 mm
β = 125.613 (5)°

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	5372 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3377 reflections with I > 2σ(I)
T_min = 0.456, T_max = 0.702	R_int = 0.028
17934 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.02	Δρ_max = 0.50 e Å⁻³
5372 reflections	Δρ_min = −0.64 e Å⁻³
244 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
Br1	0.37032 (5)	0.921319 (11)	−0.01825 (3)	0.08022 (13)
O1	0.7470 (2)	0.72827 (7)	0.16591 (14)	0.0531 (4)
O2	0.4090 (2)	0.71970 (6)	0.07684 (12)	0.0418 (3)
O3	0.2865 (2)	0.63389 (7)	−0.14111 (13)	0.0491 (3)
O4	0.4228 (2)	0.72635 (6)	−0.13204 (13)	0.0458 (3)
C1	0.6842 (4)	0.52668 (10)	0.1470 (2)	0.0553 (5)
H1A	0.7364	0.4977	0.1199	0.066*
C2	0.6125 (4)	0.50741 (10)	0.2159 (2)	0.0604 (6)
H2A	0.6172	0.4660	0.2350	0.072*
C3	0.5339 (4)	0.54928 (11)	0.2566 (2)	0.0584 (6)
H3A	0.4837	0.5362	0.3022	0.070*
C4	0.5300 (3)	0.61110 (10)	0.22937 (19)	0.0492 (5)
H4A	0.4768	0.6396	0.2566	0.059*
C5	0.6052 (3)	0.63062 (8)	0.16156 (17)	0.0401 (4)
C6	0.6811 (3)	0.58824 (9)	0.11647 (18)	0.0446 (4)
C7	0.7478 (3)	0.60440 (9)	0.03322 (19)	0.0452 (4)
C8	0.9329 (4)	0.58139 (11)	0.0623 (2)	0.0610 (6)
H8A	1.0154	0.5581	0.1359	0.073*
C9	0.9969 (4)	0.59215 (13)	−0.0146 (3)	0.0683 (7)
H9A	1.1197	0.5755	0.0068	0.082*
C10	0.8806 (4)	0.62726 (12)	−0.1228 (2)	0.0621 (6)
H10A	0.9231	0.6341	−0.1753	0.075*
C11	0.6997 (3)	0.65224 (10)	−0.1529 (2)	0.0518 (5)
H11A	0.6231	0.6775	−0.2242	0.062*
C12	0.6307 (3)	0.64009 (9)	−0.07794 (18)	0.0414 (4)
C13	0.4266 (3)	0.66420 (9)	−0.12071 (17)	0.0400 (4)
C14	0.2663 (3)	0.75862 (10)	−0.13137 (19)	0.0484 (5)
H14A	0.1485	0.7323	−0.1635	0.058*
H14B	0.2226	0.7949	−0.1849	0.058*
C15	0.3601 (3)	0.77669 (8)	0.00661 (18)	0.0412 (4)
H15A	0.4844	0.8010	0.0408	0.049*
C16	0.6025 (3)	0.69798 (9)	0.13718 (17)	0.0399 (4)
C17	0.2098 (3)	0.81201 (8)	0.01800 (17)	0.0399 (4)
C18	0.1965 (3)	0.87560 (9)	0.00813 (19)	0.0473 (5)
C19	0.0585 (4)	0.90790 (11)	0.0178 (2)	0.0612 (6)
H19A	0.0522	0.9505	0.0110	0.073*
C20	−0.0691 (4)	0.87701 (13)	0.0375 (2)	0.0657 (7)
H20A	−0.1608	0.8987	0.0453	0.079*
C21	−0.0621 (3)	0.81435 (12)	0.0458 (2)	0.0611 (6)
H21A	−0.1498	0.7934	0.0584	0.073*
C22	0.0759 (3)	0.78209 (10)	0.0353 (2)	0.0504 (5)
H22A	0.0786	0.7394	0.0401	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0990 (2)	0.04491 (14)	0.1191 (3)	−0.00504 (13)	0.0762 (2)	0.00892 (13)
O1	0.0427 (8)	0.0506 (8)	0.0540 (8)	−0.0041 (7)	0.0214 (7)	−0.0010 (7)
O2	0.0430 (7)	0.0349 (6)	0.0469 (7)	0.0056 (5)	0.0258 (6)	0.0041 (5)
O3	0.0419 (8)	0.0497 (8)	0.0541 (8)	−0.0012 (6)	0.0271 (7)	−0.0058 (6)
O4	0.0504 (8)	0.0433 (7)	0.0495 (8)	0.0067 (6)	0.0324 (7)	0.0024 (6)
C1	0.0647 (14)	0.0422 (11)	0.0456 (11)	0.0113 (10)	0.0244 (11)	0.0006 (9)
C2	0.0753 (16)	0.0403 (11)	0.0461 (12)	−0.0002 (11)	0.0244 (12)	0.0042 (9)
C3	0.0655 (15)	0.0573 (13)	0.0467 (12)	−0.0009 (11)	0.0294 (12)	0.0096 (10)
C4	0.0524 (12)	0.0512 (12)	0.0400 (10)	0.0061 (9)	0.0246 (10)	0.0046 (9)
C5	0.0373 (10)	0.0400 (9)	0.0331 (9)	0.0041 (8)	0.0150 (8)	0.0010 (7)
C6	0.0409 (11)	0.0439 (11)	0.0367 (10)	0.0063 (8)	0.0156 (9)	−0.0002 (8)
C7	0.0397 (11)	0.0452 (10)	0.0446 (11)	0.0030 (9)	0.0211 (9)	−0.0070 (8)
C8	0.0466 (13)	0.0676 (15)	0.0569 (14)	0.0138 (11)	0.0235 (11)	−0.0041 (11)
C9	0.0454 (13)	0.0843 (18)	0.0758 (17)	0.0048 (12)	0.0355 (13)	−0.0193 (14)
C10	0.0550 (14)	0.0753 (16)	0.0704 (16)	−0.0072 (12)	0.0447 (13)	−0.0154 (13)
C11	0.0491 (12)	0.0590 (13)	0.0537 (12)	−0.0024 (10)	0.0336 (11)	−0.0057 (10)
C12	0.0390 (10)	0.0414 (10)	0.0428 (10)	−0.0011 (8)	0.0232 (9)	−0.0078 (8)
C13	0.0409 (11)	0.0452 (10)	0.0334 (9)	0.0034 (8)	0.0214 (8)	−0.0025 (8)
C14	0.0519 (12)	0.0461 (11)	0.0485 (11)	0.0128 (9)	0.0300 (10)	0.0054 (9)
C15	0.0440 (11)	0.0336 (9)	0.0465 (10)	0.0039 (8)	0.0267 (9)	0.0032 (8)
C16	0.0416 (11)	0.0418 (10)	0.0332 (9)	0.0026 (8)	0.0201 (9)	−0.0024 (7)
C17	0.0402 (10)	0.0376 (9)	0.0377 (9)	0.0035 (8)	0.0203 (9)	−0.0002 (7)
C18	0.0507 (12)	0.0382 (10)	0.0498 (11)	0.0029 (9)	0.0275 (10)	0.0022 (8)
C19	0.0630 (15)	0.0455 (12)	0.0664 (15)	0.0171 (11)	0.0328 (13)	0.0001 (10)
C20	0.0539 (14)	0.0805 (18)	0.0604 (14)	0.0230 (13)	0.0320 (12)	0.0015 (12)
C21	0.0482 (13)	0.0794 (17)	0.0607 (14)	0.0060 (12)	0.0345 (12)	0.0075 (12)
C22	0.0499 (12)	0.0460 (11)	0.0554 (12)	0.0019 (9)	0.0306 (11)	0.0048 (9)

Geometric parameters (Å, º) top

Br1—C18	1.901 (2)	C9—C10	1.372 (4)
O1—C16	1.193 (2)	C9—H9A	0.9300
O2—C16	1.357 (2)	C10—C11	1.381 (3)
O2—C15	1.449 (2)	C10—H10A	0.9300
O3—C13	1.196 (2)	C11—C12	1.391 (3)
O4—C13	1.360 (2)	C11—H11A	0.9300
O4—C14	1.446 (2)	C12—C13	1.490 (3)
C1—C2	1.377 (3)	C14—C15	1.524 (3)
C1—C6	1.393 (3)	C14—H14A	0.9700
C1—H1A	0.9300	C14—H14B	0.9700
C2—C3	1.375 (3)	C15—C17	1.511 (3)
C2—H2A	0.9300	C15—H15A	0.9800
C3—C4	1.387 (3)	C17—C22	1.383 (3)
C3—H3A	0.9300	C17—C18	1.389 (3)
C4—C5	1.387 (3)	C18—C19	1.380 (3)
C4—H4A	0.9300	C19—C20	1.368 (4)
C5—C6	1.405 (3)	C19—H19A	0.9300
C5—C16	1.497 (3)	C20—C21	1.367 (4)
C6—C7	1.494 (3)	C20—H20A	0.9300
C7—C8	1.400 (3)	C21—C22	1.385 (3)
C7—C12	1.404 (3)	C21—H21A	0.9300
C8—C9	1.377 (4)	C22—H22A	0.9300
C8—H8A	0.9300

C16—O2—C15	117.39 (15)	C7—C12—C13	120.85 (17)
C13—O4—C14	116.62 (15)	O3—C13—O4	124.52 (17)
C2—C1—C6	122.0 (2)	O3—C13—C12	125.52 (18)
C2—C1—H1A	119.0	O4—C13—C12	109.95 (16)
C6—C1—H1A	119.0	O4—C14—C15	106.92 (16)
C3—C2—C1	120.2 (2)	O4—C14—H14A	110.3
C3—C2—H2A	119.9	C15—C14—H14A	110.3
C1—C2—H2A	119.9	O4—C14—H14B	110.3
C2—C3—C4	119.6 (2)	C15—C14—H14B	110.3
C2—C3—H3A	120.2	H14A—C14—H14B	108.6
C4—C3—H3A	120.2	O2—C15—C17	108.48 (15)
C3—C4—C5	120.2 (2)	O2—C15—C14	106.09 (15)
C3—C4—H4A	119.9	C17—C15—C14	111.35 (16)
C5—C4—H4A	119.9	O2—C15—H15A	110.3
C4—C5—C6	120.85 (18)	C17—C15—H15A	110.3
C4—C5—C16	118.26 (17)	C14—C15—H15A	110.3
C6—C5—C16	120.89 (17)	O1—C16—O2	124.79 (18)
C1—C6—C5	117.15 (19)	O1—C16—C5	125.73 (18)
C1—C6—C7	118.28 (18)	O2—C16—C5	109.48 (16)
C5—C6—C7	124.49 (18)	C22—C17—C18	117.32 (18)
C8—C7—C12	116.7 (2)	C22—C17—C15	121.22 (17)
C8—C7—C6	119.65 (19)	C18—C17—C15	121.44 (18)
C12—C7—C6	123.65 (17)	C19—C18—C17	121.5 (2)
C9—C8—C7	122.1 (2)	C19—C18—Br1	117.61 (17)
C9—C8—H8A	118.9	C17—C18—Br1	120.89 (15)
C7—C8—H8A	118.9	C20—C19—C18	119.7 (2)
C10—C9—C8	120.4 (2)	C20—C19—H19A	120.1
C10—C9—H9A	119.8	C18—C19—H19A	120.1
C8—C9—H9A	119.8	C21—C20—C19	120.2 (2)
C9—C10—C11	119.3 (2)	C21—C20—H20A	119.9
C9—C10—H10A	120.4	C19—C20—H20A	119.9
C11—C10—H10A	120.4	C20—C21—C22	119.8 (2)
C10—C11—C12	120.7 (2)	C20—C21—H21A	120.1
C10—C11—H11A	119.6	C22—C21—H21A	120.1
C12—C11—H11A	119.6	C17—C22—C21	121.3 (2)
C11—C12—C7	120.75 (18)	C17—C22—H22A	119.3
C11—C12—C13	118.37 (18)	C21—C22—H22A	119.3

C6—C1—C2—C3	0.2 (3)	C7—C12—C13—O3	−55.8 (3)
C1—C2—C3—C4	−0.9 (3)	C11—C12—C13—O4	−58.4 (2)
C2—C3—C4—C5	−0.1 (3)	C7—C12—C13—O4	123.48 (18)
C3—C4—C5—C6	1.8 (3)	C13—O4—C14—C15	92.45 (19)
C3—C4—C5—C16	−178.53 (18)	C16—O2—C15—C17	−145.27 (15)
C2—C1—C6—C5	1.4 (3)	C16—O2—C15—C14	95.00 (18)
C2—C1—C6—C7	−175.6 (2)	O4—C14—C15—O2	−63.25 (19)
C4—C5—C6—C1	−2.3 (3)	O4—C14—C15—C17	178.92 (15)
C16—C5—C6—C1	177.95 (18)	C15—O2—C16—O1	20.9 (3)
C4—C5—C6—C7	174.39 (18)	C15—O2—C16—C5	−159.12 (15)
C16—C5—C6—C7	−5.3 (3)	C4—C5—C16—O1	124.1 (2)
C1—C6—C7—C8	−49.6 (3)	C6—C5—C16—O1	−56.2 (3)
C5—C6—C7—C8	133.7 (2)	C4—C5—C16—O2	−55.9 (2)
C1—C6—C7—C12	127.8 (2)	C6—C5—C16—O2	123.83 (18)
C5—C6—C7—C12	−48.9 (3)	O2—C15—C17—C22	−28.2 (2)
C12—C7—C8—C9	−1.0 (3)	C14—C15—C17—C22	88.2 (2)
C6—C7—C8—C9	176.6 (2)	O2—C15—C17—C18	153.52 (17)
C7—C8—C9—C10	1.1 (4)	C14—C15—C17—C18	−90.1 (2)
C8—C9—C10—C11	0.7 (4)	C22—C17—C18—C19	1.3 (3)
C9—C10—C11—C12	−2.7 (4)	C15—C17—C18—C19	179.6 (2)
C10—C11—C12—C7	2.9 (3)	C22—C17—C18—Br1	−179.10 (15)
C10—C11—C12—C13	−175.23 (19)	C15—C17—C18—Br1	−0.8 (3)
C8—C7—C12—C11	−1.0 (3)	C17—C18—C19—C20	0.0 (4)
C6—C7—C12—C11	−178.45 (19)	Br1—C18—C19—C20	−179.65 (18)
C8—C7—C12—C13	177.03 (18)	C18—C19—C20—C21	−0.9 (4)
C6—C7—C12—C13	−0.4 (3)	C19—C20—C21—C22	0.6 (4)
C14—O4—C13—O3	19.0 (3)	C18—C17—C22—C21	−1.7 (3)
C14—O4—C13—C12	−160.36 (15)	C15—C17—C22—C21	−179.99 (19)
C11—C12—C13—O3	122.3 (2)	C20—C21—C22—C17	0.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21A···O1ⁱ	0.93	2.44	3.321 (3)	158

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₅BrO₄
M_r	423.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.0436 (9), 21.775 (2), 12.8809 (11)
β (°)	125.613 (5)
V (Å³)	1834.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.27
Crystal size (mm)	0.41 × 0.23 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.456, 0.702
No. of measured, independent and observed [I > 2σ(I)] reflections	17934, 5372, 3377
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.102, 1.02
No. of reflections	5372
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.64

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
C21—H21A···O1ⁱ	0.93	2.44	3.321 (3)	158

Symmetry code: (i) x−1, y, z.

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

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K., Quah, C. K. & Wu, D. (2012). Acta Cryst. E68, accepted [IS5123]. 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