5-Bromo-2-(4-fluoro­phen­yl)-7-methyl-3-phenyl­sulfinyl-1-benzo­furan

Choi, H.D.; Seo, P.J.; Lee, U.

doi:10.1107/S1600536813016760

5-Bromo-2-(4-fluorophenyl)-7-methyl-3-phenylsulfinyl-1-benzofuran

In the title compound, C₂₁H₁₄BrFO₂S, the dihedral angles between the mean plane [r.m.s. deviation = 0.005 (1) Å] of the benzofuran ring system and the pendant 4-fluorophenyl and phenyl rings are 1.50 (8) and 81.47 (6)°, respectively. In the crystal, molecules are linked by weak C—H

O hydrogen bonds into supramolecular chains running along the a-axis direction. A short S

O contact [2.9623 (13) Å] involving the sulfinyl groups is observed between inversion-related chains.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536813016760/xu5714sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536813016760/xu5714Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536813016760/xu5714Isup3.cml Supplementary material

CCDC reference: 962134

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R factor = 0.029
wR factor = 0.075
Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ? Do !
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00100 Deg.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         23

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

As a part of our continuing study of 5-bromo-3-phenylsulfinyl-1-benzofuran derivatives containing phenyl (Choi et al., 2009) and 4-fluorophenyl (Seo et al., 2011) substituents in 2-position, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.005 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angles between the mean plane of the benzofuran ring system and the pendant 4-fluorophenyl and phenyl rings are 1.50 (8) and 81.47 (6)°, respectively. In the crystal structure (Fig. 2), molecules are connected by weak C—H···O hydrogen bonds (Table 1) into chains extending along the a-axis direction, these chains are further packed into stacks by a sulfinyl–sulfinyl interaction (Choi et al., 2008) interpreted as similar to a type-ll carbonyl–carbonyl interaction (Allen et al., 1998), with a S1···O2ⁱⁱ distance of 2.9623 (13) Å [symmetry code: (ii) 1- x, - y, 1- z].

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2009); Seo et al. (2011). For details of sulfinyl–sulfinyl interactions, see: Choi et al. (2008). For a review of carbonyl–carbonyl interactions, see: Allen et al. (1998).

Experimental top

3-Chloroperoxybenzoic acid (77%, 202 mg, 0.9 mmol) was added in small portions to a stirred solution of 5-bromo-2-(4-fluorophenyl)-7-methyl-3-phenylsulfanyl-1-benzofuran (330 mg, 0.8 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 5h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane-ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 56%, m.p. 485–486 K; R_f = 0.72 (hexane–ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in benzene at room temperature.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the C—H···O and S···O interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) -1+x, y, z; (ii) 1+x, y, z; (iii) - x + 1, - y, - z + 1].

5-Bromo-2-(4-fluorophenyl)-7-methyl-3-phenylsulfinyl-1-benzofuran top

Crystal data top

C₂₁H₁₄BrFO₂S	Z = 2
M_r = 429.29	F(000) = 432
Triclinic, P1	D_x = 1.640 Mg m⁻³
Hall symbol: -P 1	Melting point = 485–486 K
a = 7.9961 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6641 (2) Å	Cell parameters from 9897 reflections
c = 11.1695 (2) Å	θ = 2.4–28.2°
α = 71.980 (1)°	µ = 2.51 mm⁻¹
β = 74.694 (1)°	T = 173 K
γ = 79.964 (1)°	Block, colourless
V = 869.13 (3) Å³	0.30 × 0.24 × 0.18 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	4315 independent reflections
Radiation source: rotating anode	3839 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.042
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.4°, θ_min = 2.0°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
T_min = 0.523, T_max = 0.665	l = −14→14
20230 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)] = 0.029	Hydrogen site location: difference Fourier map
wR(F²) = 0.075	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0333P)² + 0.4794P] where P = (F_o² + 2F_c²)/3
4315 reflections	(Δ/σ)_max = 0.003
236 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

C₂₁H₁₄BrFO₂S	γ = 79.964 (1)°
M_r = 429.29	V = 869.13 (3) Å³
Triclinic, P1	Z = 2
a = 7.9961 (2) Å	Mo Kα radiation
b = 10.6641 (2) Å	µ = 2.51 mm⁻¹
c = 11.1695 (2) Å	T = 173 K
α = 71.980 (1)°	0.30 × 0.24 × 0.18 mm
β = 74.694 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4315 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3839 reflections with I > 2σ(I)
T_min = 0.523, T_max = 0.665	R_int = 0.042
20230 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.05	Δρ_max = 0.41 e Å⁻³
4315 reflections	Δρ_min = −0.54 e Å⁻³
236 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	0.53307 (3)	0.21563 (2)	1.020561 (18)	0.03609 (8)
S1	0.37815 (5)	0.14799 (4)	0.52980 (4)	0.02275 (10)
F1	0.03254 (17)	0.61879 (13)	0.03936 (11)	0.0404 (3)
O1	0.26465 (16)	0.51907 (12)	0.55316 (11)	0.0224 (2)
O2	0.53338 (17)	0.07965 (13)	0.58227 (14)	0.0314 (3)
C1	0.3368 (2)	0.30250 (16)	0.56610 (16)	0.0210 (3)
C2	0.3727 (2)	0.32575 (17)	0.67753 (17)	0.0218 (3)
C3	0.4376 (2)	0.24909 (18)	0.78483 (17)	0.0245 (3)
H3	0.4730	0.1570	0.7975	0.029*
C4	0.4476 (2)	0.31452 (19)	0.87148 (17)	0.0266 (4)
C5	0.3997 (2)	0.44971 (19)	0.85545 (17)	0.0268 (4)
H5	0.4103	0.4888	0.9185	0.032*
C6	0.3367 (2)	0.52804 (18)	0.74877 (17)	0.0236 (3)
C7	0.3256 (2)	0.46035 (17)	0.66358 (16)	0.0217 (3)
C8	0.2727 (2)	0.42141 (16)	0.49445 (16)	0.0207 (3)
C9	0.2845 (3)	0.67413 (19)	0.7268 (2)	0.0319 (4)
H9A	0.2781	0.7145	0.6363	0.048*
H9B	0.3711	0.7146	0.7468	0.048*
H9C	0.1703	0.6887	0.7830	0.048*
C10	0.2095 (2)	0.46846 (17)	0.37493 (16)	0.0216 (3)
C11	0.2097 (2)	0.38651 (18)	0.29886 (17)	0.0264 (4)
H11	0.2505	0.2953	0.3251	0.032*
C12	0.1508 (3)	0.4366 (2)	0.18517 (18)	0.0287 (4)
H12	0.1520	0.3810	0.1328	0.034*
C13	0.0906 (2)	0.56897 (19)	0.15021 (17)	0.0274 (4)
C14	0.0875 (2)	0.65295 (19)	0.22250 (18)	0.0295 (4)
H14	0.0446	0.7437	0.1960	0.035*
C15	0.1482 (2)	0.60225 (18)	0.33472 (17)	0.0258 (4)
H15	0.1482	0.6592	0.3854	0.031*
C16	0.1908 (2)	0.07458 (17)	0.64136 (18)	0.0240 (3)
C17	0.2020 (3)	0.00195 (19)	0.7657 (2)	0.0320 (4)
H17	0.3086	−0.0096	0.7921	0.038*
C18	0.0577 (3)	−0.0536 (2)	0.8510 (2)	0.0418 (5)
H18	0.0643	−0.1030	0.9368	0.050*
C19	−0.0970 (3)	−0.0370 (2)	0.8114 (3)	0.0456 (6)
H19	−0.1967	−0.0747	0.8706	0.055*
C20	−0.1076 (3)	0.0339 (2)	0.6864 (3)	0.0451 (6)
H20	−0.2138	0.0444	0.6598	0.054*
C21	0.0378 (3)	0.0897 (2)	0.6001 (2)	0.0323 (4)
H21	0.0324	0.1376	0.5138	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03889 (12)	0.04419 (13)	0.02697 (11)	−0.00605 (9)	−0.01581 (8)	−0.00429 (8)
S1	0.0246 (2)	0.0195 (2)	0.0269 (2)	0.00332 (16)	−0.00942 (17)	−0.01036 (16)
F1	0.0500 (7)	0.0448 (7)	0.0276 (6)	−0.0031 (6)	−0.0208 (5)	−0.0026 (5)
O1	0.0284 (6)	0.0190 (6)	0.0217 (6)	−0.0010 (5)	−0.0067 (5)	−0.0080 (5)
O2	0.0268 (6)	0.0291 (7)	0.0435 (8)	0.0083 (5)	−0.0169 (6)	−0.0160 (6)
C1	0.0225 (8)	0.0198 (8)	0.0220 (8)	−0.0013 (6)	−0.0052 (6)	−0.0078 (6)
C2	0.0198 (7)	0.0231 (8)	0.0241 (8)	−0.0029 (6)	−0.0045 (6)	−0.0088 (7)
C3	0.0234 (8)	0.0241 (8)	0.0263 (8)	−0.0025 (7)	−0.0070 (7)	−0.0063 (7)
C4	0.0241 (8)	0.0333 (10)	0.0228 (8)	−0.0071 (7)	−0.0073 (7)	−0.0045 (7)
C5	0.0267 (9)	0.0341 (10)	0.0237 (8)	−0.0087 (7)	−0.0028 (7)	−0.0132 (7)
C6	0.0230 (8)	0.0252 (9)	0.0248 (8)	−0.0069 (7)	−0.0013 (7)	−0.0108 (7)
C7	0.0227 (8)	0.0226 (8)	0.0202 (8)	−0.0042 (6)	−0.0041 (6)	−0.0062 (6)
C8	0.0218 (8)	0.0204 (8)	0.0216 (8)	−0.0022 (6)	−0.0033 (6)	−0.0096 (6)
C9	0.0400 (11)	0.0273 (9)	0.0325 (10)	−0.0052 (8)	−0.0068 (8)	−0.0142 (8)
C10	0.0202 (8)	0.0233 (8)	0.0197 (8)	−0.0020 (6)	−0.0028 (6)	−0.0055 (6)
C11	0.0302 (9)	0.0241 (9)	0.0251 (8)	−0.0003 (7)	−0.0082 (7)	−0.0068 (7)
C12	0.0325 (9)	0.0328 (10)	0.0244 (9)	−0.0046 (8)	−0.0080 (7)	−0.0108 (7)
C13	0.0260 (8)	0.0342 (10)	0.0194 (8)	−0.0041 (7)	−0.0069 (7)	−0.0016 (7)
C14	0.0305 (9)	0.0269 (9)	0.0263 (9)	0.0017 (7)	−0.0068 (7)	−0.0027 (7)
C15	0.0286 (9)	0.0237 (9)	0.0245 (8)	0.0002 (7)	−0.0054 (7)	−0.0080 (7)
C16	0.0263 (8)	0.0166 (8)	0.0320 (9)	0.0005 (6)	−0.0097 (7)	−0.0097 (7)
C17	0.0379 (10)	0.0236 (9)	0.0355 (10)	−0.0036 (8)	−0.0150 (8)	−0.0033 (8)
C18	0.0525 (13)	0.0287 (10)	0.0405 (12)	−0.0096 (10)	−0.0072 (10)	−0.0042 (9)
C19	0.0402 (12)	0.0361 (12)	0.0577 (15)	−0.0130 (10)	0.0039 (11)	−0.0166 (11)
C20	0.0289 (10)	0.0455 (13)	0.0706 (16)	−0.0040 (9)	−0.0139 (11)	−0.0275 (12)
C21	0.0320 (10)	0.0315 (10)	0.0406 (11)	0.0014 (8)	−0.0163 (8)	−0.0157 (8)

Geometric parameters (Å, º) top

Br1—C4	1.9013 (18)	C9—H9C	0.9800
S1—O2	1.4899 (13)	C10—C11	1.394 (2)
S1—C1	1.7723 (17)	C10—C15	1.398 (2)
S1—C16	1.7972 (19)	C11—C12	1.388 (3)
S1—O2ⁱ	2.9623 (13)	C11—H11	0.9500
F1—C13	1.357 (2)	C12—C13	1.378 (3)
O1—C7	1.373 (2)	C12—H12	0.9500
O1—C8	1.377 (2)	C13—C14	1.372 (3)
C1—C8	1.368 (2)	C14—C15	1.382 (3)
C1—C2	1.448 (2)	C14—H14	0.9500
C2—C7	1.389 (2)	C15—H15	0.9500
C2—C3	1.396 (2)	C16—C17	1.383 (3)
C3—C4	1.381 (3)	C16—C21	1.384 (3)
C3—H3	0.9500	C17—C18	1.378 (3)
C4—C5	1.393 (3)	C17—H17	0.9500
C5—C6	1.388 (3)	C18—C19	1.387 (4)
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.388 (2)	C19—C20	1.383 (4)
C6—C9	1.501 (3)	C19—H19	0.9500
C8—C10	1.464 (2)	C20—C21	1.389 (3)
C9—H9A	0.9800	C20—H20	0.9500
C9—H9B	0.9800	C21—H21	0.9500

O2—S1—C1	105.07 (8)	C11—C10—C15	118.65 (16)
O2—S1—C16	107.03 (8)	C11—C10—C8	123.09 (16)
C1—S1—C16	97.33 (8)	C15—C10—C8	118.26 (15)
O2—S1—O2ⁱ	79.03 (6)	C12—C11—C10	120.80 (17)
C1—S1—O2ⁱ	169.13 (7)	C12—C11—H11	119.6
C16—S1—O2ⁱ	90.93 (6)	C10—C11—H11	119.6
C7—O1—C8	107.06 (13)	C13—C12—C11	118.30 (17)
C8—C1—C2	107.30 (14)	C13—C12—H12	120.8
C8—C1—S1	127.61 (13)	C11—C12—H12	120.8
C2—C1—S1	125.05 (13)	F1—C13—C14	118.48 (17)
C7—C2—C3	119.02 (16)	F1—C13—C12	118.73 (17)
C7—C2—C1	104.82 (15)	C14—C13—C12	122.80 (17)
C3—C2—C1	136.16 (16)	C13—C14—C15	118.36 (17)
C4—C3—C2	116.31 (16)	C13—C14—H14	120.8
C4—C3—H3	121.8	C15—C14—H14	120.8
C2—C3—H3	121.8	C14—C15—C10	121.08 (17)
C3—C4—C5	123.66 (17)	C14—C15—H15	119.5
C3—C4—Br1	118.48 (14)	C10—C15—H15	119.5
C5—C4—Br1	117.85 (13)	C17—C16—C21	121.00 (19)
C6—C5—C4	120.97 (16)	C17—C16—S1	119.87 (14)
C6—C5—H5	119.5	C21—C16—S1	119.11 (15)
C4—C5—H5	119.5	C18—C17—C16	119.7 (2)
C7—C6—C5	114.56 (16)	C18—C17—H17	120.2
C7—C6—C9	122.50 (17)	C16—C17—H17	120.2
C5—C6—C9	122.94 (16)	C17—C18—C19	119.8 (2)
O1—C7—C6	123.77 (15)	C17—C18—H18	120.1
O1—C7—C2	110.76 (14)	C19—C18—H18	120.1
C6—C7—C2	125.47 (16)	C20—C19—C18	120.6 (2)
C1—C8—O1	110.06 (15)	C20—C19—H19	119.7
C1—C8—C10	136.22 (16)	C18—C19—H19	119.7
O1—C8—C10	113.71 (14)	C19—C20—C21	119.7 (2)
C6—C9—H9A	109.5	C19—C20—H20	120.1
C6—C9—H9B	109.5	C21—C20—H20	120.1
H9A—C9—H9B	109.5	C16—C21—C20	119.2 (2)
C6—C9—H9C	109.5	C16—C21—H21	120.4
H9A—C9—H9C	109.5	C20—C21—H21	120.4
H9B—C9—H9C	109.5

O2—S1—C1—C8	146.26 (16)	S1—C1—C8—C10	3.3 (3)
C16—S1—C1—C8	−103.83 (17)	C7—O1—C8—C1	0.28 (18)
O2ⁱ—S1—C1—C8	35.4 (4)	C7—O1—C8—C10	179.29 (14)
O2—S1—C1—C2	−31.09 (17)	C1—C8—C10—C11	−2.7 (3)
C16—S1—C1—C2	78.82 (16)	O1—C8—C10—C11	178.64 (15)
O2ⁱ—S1—C1—C2	−142.0 (3)	C1—C8—C10—C15	178.07 (19)
C8—C1—C2—C7	0.15 (19)	O1—C8—C10—C15	−0.6 (2)
S1—C1—C2—C7	177.95 (13)	C15—C10—C11—C12	0.3 (3)
C8—C1—C2—C3	−180.0 (2)	C8—C10—C11—C12	−178.96 (17)
S1—C1—C2—C3	−2.2 (3)	C10—C11—C12—C13	−0.7 (3)
C7—C2—C3—C4	0.9 (2)	C11—C12—C13—F1	−179.89 (17)
C1—C2—C3—C4	−178.93 (19)	C11—C12—C13—C14	0.4 (3)
C2—C3—C4—C5	−1.0 (3)	F1—C13—C14—C15	−179.41 (16)
C2—C3—C4—Br1	179.48 (13)	C12—C13—C14—C15	0.3 (3)
C3—C4—C5—C6	0.3 (3)	C13—C14—C15—C10	−0.8 (3)
Br1—C4—C5—C6	179.83 (14)	C11—C10—C15—C14	0.5 (3)
C4—C5—C6—C7	0.4 (3)	C8—C10—C15—C14	179.73 (16)
C4—C5—C6—C9	−179.60 (17)	O2—S1—C16—C17	17.79 (17)
C8—O1—C7—C6	−179.86 (16)	C1—S1—C16—C17	−90.49 (15)
C8—O1—C7—C2	−0.18 (19)	O2ⁱ—S1—C16—C17	96.59 (15)
C5—C6—C7—O1	179.15 (15)	O2—S1—C16—C21	−160.92 (14)
C9—C6—C7—O1	−0.8 (3)	C1—S1—C16—C21	90.81 (15)
C5—C6—C7—C2	−0.5 (3)	O2ⁱ—S1—C16—C21	−82.11 (14)
C9—C6—C7—C2	179.53 (17)	C21—C16—C17—C18	−1.7 (3)
C3—C2—C7—O1	−179.89 (15)	S1—C16—C17—C18	179.67 (15)
C1—C2—C7—O1	0.02 (19)	C16—C17—C18—C19	0.5 (3)
C3—C2—C7—C6	−0.2 (3)	C17—C18—C19—C20	0.5 (3)
C1—C2—C7—C6	179.69 (17)	C18—C19—C20—C21	−0.4 (3)
C2—C1—C8—O1	−0.27 (19)	C17—C16—C21—C20	1.8 (3)
S1—C1—C8—O1	−178.00 (12)	S1—C16—C21—C20	−179.50 (15)
C2—C1—C8—C10	−178.96 (19)	C19—C20—C21—C16	−0.8 (3)

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
C20—H20···O2ⁱⁱ	0.95	2.33	3.280 (3)	176

Symmetry code: (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₄BrFO₂S
M_r	429.29
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.9961 (2), 10.6641 (2), 11.1695 (2)
α, β, γ (°)	71.980 (1), 74.694 (1), 79.964 (1)
V (Å³)	869.13 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.51
Crystal size (mm)	0.30 × 0.24 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.523, 0.665
No. of measured, independent and observed [I > 2σ(I)] reflections	20230, 4315, 3839
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.075, 1.05
No. of reflections	4315
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.54

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998).