3-(4-Fluoro­phenyl­sulfon­yl)-5-isopropyl-2-methyl-1-benzofuran

Choi, H.D.; Seo, P.J.; Son, B.W.; Lee, U.

doi:10.1107/S1600536810012869

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1067

https://doi.org/10.1107/S1600536810012869

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3-(4-Fluorophenylsulfonyl)-5-isopropyl-2-methyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo,^a Byeng Wha Son ^b and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
^*Correspondence e-mail: uklee@pknu.ac.kr

(Received 6 April 2010; accepted 7 April 2010; online 14 April 2010)

In the title compound, C₁₈H₁₇FO₃S, the 4-fluorophenyl ring makes a dihedral angle of 82.12 (4)° with the plane of the benzofuran fragment. In the crystal structure, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions.

Related literature

For the crystal structures of similar 2-methyl-3-phenylsulfonyl-1-benzofuran derivatives, see: Choi et al. (2008a ,b ). For the biological activity of benzofuran compounds, see: Aslam et al. (2006 ); Galal et al. (2009 ); Khan et al. (2005 ). For natural products with benzofuran rings, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ).

Experimental

Crystal data

C₁₈H₁₇FO₃S
M_r = 332.38
Monoclinic, P 2₁ /c
a = 10.9434 (6) Å
b = 11.3395 (6) Å
c = 13.0988 (7) Å
β = 100.252 (3)°
V = 1599.51 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 175 K
0.41 × 0.29 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.669, T_max = 0.746
14304 measured reflections
3655 independent reflections
3109 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.108
S = 1.02
3655 reflections
212 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1/C2/C7/O3/C8 furan ring and the C2–C7 benzene ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O2ⁱ	0.95	2.51	3.401 (2)	155
C10—H10B⋯Cg1ⁱⁱ	0.98	2.86	3.561 (2)	120
C11—H11B⋯Cg2ⁱⁱ	0.98	2.91	3.670 (2)	135
C17—H17⋯Cg2ⁱⁱⁱ	0.95	2.89	3.528 (2)	147
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810012869/xu2750sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810012869/xu2750Isup2.hkl

checkCIF report

Comment top

The compounds containing benzofuran ring show potent biological activities such as antifungal (Aslam et al., 2006), antitumor and antiviral (Galal et al., 2009), antimicrobial (Khan et al., 2005) properties. These compounds occur widely in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing studies of the effect of side chain substituents on the solid state structures of 2-methyl-3-phenylsulfonyl-1-benzofuran analogues (Choi et al., 2008a,b), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.113 (1) Å from the least-squares plane defined by the nine constituent atoms. The 4-fluorophenyl ring makes a dihedral angle of 82.12 (4)° with the plane of the benzofuran fragment. The molecular packing (Fig. 2) is stabilized by an intermolecular C—H···O hydrogen bond between the 4-fluorophenyl H atom and the oxygen of the sulfonyl group, with a C14—H14···O2ⁱ (Table 1). The crystal packing (Fig. 3) is further stabilized by three intermolecular C—H···π interactions; the first one between the methyl H atom of the isopropyl group and the furan ring of an adjacent molecule, with a C10—H10B···Cg1ⁱⁱ, the second one between the methyl H atom of the isopropyl group and the benzene ring of a neighbouring molecule, with a C11—H11B···Cg2ⁱⁱ, and the third one between the 4-fluorophenyl H atom and the benzene ring of an adjacent benzofuran system, with a C17—H17···Cg2ⁱⁱⁱ, respectively (Table 1; Cg1 and Cg2 are the centroids of the C1/C2/C7/O3/C8 furan ring and the C2–C7 benzene ring, respectively).

Related literature top

For the crystal structures of similar 2-methyl-3-phenylsulfonyl-1-benzofuran derivatives, see: Choi et al. (2008a,b). For the biological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003).

Experimental top

77% 3-Chloroperoxybenzoic acid (448 mg, 2.0 mmol) was added in small portions to a stirred solution of 3-(4-fluorophenylsulfanyl)-5-isoproyl-2-methyl-1-benzofuran (270 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 8 h, 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 (silica gel, hexane–ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 79%, m.p. 402–403 K; Rf = 0.69 (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

For the crystal structures of similar 2-methyl-3-phenylsulfonyl-1-benzofuran derivatives, see: Choi et al. (2008a,b). For the biological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003).

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 (Farrugia, 1997) 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 a small spheres of arbitrary radius.
	Fig. 2. C—H···O interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) -x + 1, y - 1/2, -z + 1/2; (iv) -x + 1, y + 1/2, -z + 1/2; (v) x, y + 1, z.]
	Fig. 3. C—H···π interactions (dotted lines) in the crystal structure of the title compound. Cg denotes the ring centroid. [Symmetry codes: (ii) -x + 2, y + 1/2, -z + 1/2; (iii) x, -y + 1/2, z - 1/2; (vi) -x + 2, y - 1/2, -z + 1/2; (vii) x, -y + 1/2, z + 1/2.]

3-(4-Fluorophenylsulfonyl)-5-isopropyl-2-methyl-1-benzofuran top

Crystal data top

C₁₈H₁₇FO₃S	F(000) = 696
M_r = 332.38	D_x = 1.380 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6367 reflections
a = 10.9434 (6) Å	θ = 2.4–27.5°
b = 11.3395 (6) Å	µ = 0.23 mm⁻¹
c = 13.0988 (7) Å	T = 175 K
β = 100.252 (3)°	Block, colourless
V = 1599.51 (15) Å³	0.41 × 0.29 × 0.17 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	3655 independent reflections
Radiation source: rotating anode	3109 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.030
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 2.4°
φ and ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
T_min = 0.669, T_max = 0.746	l = −16→16
14304 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.108	w = 1/[σ²(F_o²) + (0.0594P)² + 0.4509P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3655 reflections	Δρ_max = 0.36 e Å⁻³
212 parameters	Δρ_min = −0.37 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0117 (15)

Crystal data top

C₁₈H₁₇FO₃S	V = 1599.51 (15) Å³
M_r = 332.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.9434 (6) Å	µ = 0.23 mm⁻¹
b = 11.3395 (6) Å	T = 175 K
c = 13.0988 (7) Å	0.41 × 0.29 × 0.17 mm
β = 100.252 (3)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3655 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3109 reflections with I > 2σ(I)
T_min = 0.669, T_max = 0.746	R_int = 0.030
14304 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.02	Δρ_max = 0.36 e Å⁻³
3655 reflections	Δρ_min = −0.37 e Å⁻³
212 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
S	0.54221 (3)	0.13196 (3)	0.21925 (3)	0.02922 (13)
F	0.75485 (9)	−0.21439 (9)	−0.02852 (8)	0.0475 (3)
O1	0.44396 (10)	0.07695 (11)	0.26153 (9)	0.0415 (3)
O2	0.51752 (10)	0.23800 (9)	0.15885 (8)	0.0367 (3)
O3	0.79447 (10)	0.15165 (9)	0.47328 (8)	0.0300 (2)
C1	0.66335 (13)	0.16383 (12)	0.32124 (11)	0.0268 (3)
C2	0.75540 (12)	0.25570 (12)	0.32202 (10)	0.0244 (3)
C3	0.78117 (13)	0.34256 (12)	0.25361 (11)	0.0270 (3)
H3	0.7288	0.3527	0.1881	0.032*
C4	0.88480 (13)	0.41423 (13)	0.28261 (11)	0.0285 (3)
C5	0.96004 (13)	0.39900 (13)	0.38020 (11)	0.0302 (3)
H5	1.0300	0.4491	0.3993	0.036*
C6	0.93628 (13)	0.31367 (13)	0.44994 (11)	0.0297 (3)
H6	0.9877	0.3038	0.5159	0.036*
C7	0.83340 (13)	0.24398 (12)	0.41752 (10)	0.0257 (3)
C8	0.69246 (14)	0.10323 (13)	0.41204 (11)	0.0303 (3)
C9	0.91774 (15)	0.50549 (14)	0.20723 (12)	0.0356 (4)
H9	0.8483	0.5073	0.1462	0.043*
C10	1.0351 (2)	0.47032 (18)	0.16761 (16)	0.0548 (5)
H10A	1.1061	0.4728	0.2249	0.082*
H10B	1.0492	0.5253	0.1132	0.082*
H10C	1.0256	0.3902	0.1392	0.082*
C11	0.9299 (2)	0.62926 (15)	0.25374 (16)	0.0531 (5)
H11A	0.8558	0.6477	0.2832	0.080*
H11B	0.9381	0.6866	0.1994	0.080*
H11C	1.0036	0.6329	0.3085	0.080*
C12	0.64435 (18)	−0.00464 (15)	0.45463 (14)	0.0452 (4)
H12A	0.5675	−0.0294	0.4094	0.068*
H12B	0.6275	0.0117	0.5243	0.068*
H12C	0.7062	−0.0677	0.4584	0.068*
C13	0.60386 (13)	0.02725 (12)	0.14291 (11)	0.0274 (3)
C14	0.60321 (15)	−0.09153 (13)	0.16991 (12)	0.0342 (3)
H14	0.5684	−0.1159	0.2279	0.041*
C15	0.65382 (15)	−0.17364 (14)	0.11133 (13)	0.0375 (4)
H15	0.6546	−0.2551	0.1283	0.045*
C16	0.70315 (14)	−0.13427 (13)	0.02763 (13)	0.0332 (3)
C17	0.70304 (14)	−0.01834 (14)	−0.00155 (12)	0.0344 (3)
H17	0.7364	0.0049	−0.0606	0.041*
C18	0.65300 (14)	0.06423 (13)	0.05734 (12)	0.0309 (3)
H18	0.6523	0.1454	0.0394	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0237 (2)	0.0283 (2)	0.0349 (2)	−0.00195 (13)	0.00319 (14)	−0.00717 (14)
F	0.0421 (6)	0.0428 (6)	0.0595 (7)	0.0017 (4)	0.0145 (5)	−0.0195 (5)
O1	0.0295 (6)	0.0473 (7)	0.0503 (7)	−0.0098 (5)	0.0138 (5)	−0.0133 (5)
O2	0.0336 (6)	0.0308 (6)	0.0412 (6)	0.0052 (4)	−0.0057 (5)	−0.0056 (5)
O3	0.0344 (6)	0.0300 (5)	0.0254 (5)	−0.0011 (4)	0.0047 (4)	0.0015 (4)
C1	0.0263 (7)	0.0248 (7)	0.0296 (7)	−0.0011 (5)	0.0061 (5)	−0.0042 (5)
C2	0.0238 (6)	0.0237 (7)	0.0254 (7)	0.0010 (5)	0.0033 (5)	−0.0044 (5)
C3	0.0282 (7)	0.0272 (7)	0.0238 (7)	−0.0006 (5)	0.0001 (5)	−0.0015 (5)
C4	0.0309 (7)	0.0270 (7)	0.0280 (7)	−0.0026 (6)	0.0060 (6)	−0.0031 (6)
C5	0.0276 (7)	0.0305 (7)	0.0317 (8)	−0.0043 (6)	0.0032 (6)	−0.0058 (6)
C6	0.0299 (7)	0.0317 (7)	0.0253 (7)	0.0021 (6)	−0.0009 (5)	−0.0044 (6)
C7	0.0296 (7)	0.0248 (7)	0.0229 (7)	0.0026 (5)	0.0055 (5)	−0.0014 (5)
C8	0.0318 (7)	0.0298 (7)	0.0307 (8)	−0.0016 (6)	0.0096 (6)	−0.0033 (6)
C9	0.0429 (9)	0.0341 (8)	0.0288 (7)	−0.0112 (7)	0.0035 (6)	0.0009 (6)
C10	0.0683 (13)	0.0476 (11)	0.0569 (12)	−0.0131 (9)	0.0341 (10)	−0.0023 (9)
C11	0.0834 (14)	0.0304 (9)	0.0503 (11)	−0.0054 (9)	0.0247 (10)	0.0037 (8)
C12	0.0516 (10)	0.0413 (9)	0.0444 (10)	−0.0111 (8)	0.0130 (8)	0.0077 (8)
C13	0.0245 (7)	0.0263 (7)	0.0302 (7)	−0.0030 (5)	0.0023 (5)	−0.0041 (6)
C14	0.0398 (8)	0.0281 (7)	0.0351 (8)	−0.0050 (6)	0.0080 (6)	−0.0006 (6)
C15	0.0423 (9)	0.0249 (7)	0.0445 (9)	−0.0006 (6)	0.0054 (7)	−0.0022 (7)
C16	0.0248 (7)	0.0340 (8)	0.0396 (9)	−0.0004 (6)	0.0029 (6)	−0.0126 (6)
C17	0.0315 (8)	0.0378 (8)	0.0349 (8)	−0.0083 (6)	0.0087 (6)	−0.0040 (6)
C18	0.0303 (7)	0.0269 (7)	0.0350 (8)	−0.0057 (6)	0.0046 (6)	−0.0004 (6)

Geometric parameters (Å, º) top

S—O1	1.437 (1)	C9—C11	1.526 (2)
S—O2	1.438 (1)	C9—H9	1.0000
S—C1	1.744 (2)	C10—H10A	0.9800
S—C13	1.762 (1)	C10—H10B	0.9800
F—C16	1.355 (2)	C10—H10C	0.9800
O3—C8	1.368 (2)	C11—H11A	0.9800
O3—C7	1.386 (2)	C11—H11B	0.9800
C1—C8	1.361 (2)	C11—H11C	0.9800
C1—C2	1.448 (2)	C12—H12A	0.9800
C2—C7	1.390 (2)	C12—H12B	0.9800
C2—C3	1.394 (2)	C12—H12C	0.9800
C3—C4	1.392 (2)	C13—C14	1.393 (2)
C3—H3	0.9500	C13—C18	1.391 (2)
C4—C5	1.403 (2)	C14—C15	1.383 (2)
C4—C9	1.517 (2)	C14—H14	0.9500
C5—C6	1.387 (2)	C15—C16	1.380 (2)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.379 (2)	C16—C17	1.369 (2)
C6—H6	0.9500	C17—C18	1.386 (2)
C8—C12	1.480 (2)	C17—H17	0.9500
C9—C10	1.521 (2)	C18—H18	0.9500

O1—S—O2	119.66 (7)	C9—C10—H10A	109.5
O1—S—C1	108.28 (7)	C9—C10—H10B	109.5
O2—S—C1	106.91 (7)	H10A—C10—H10B	109.5
O1—S—C13	108.33 (7)	C9—C10—H10C	109.5
O2—S—C13	107.74 (7)	H10A—C10—H10C	109.5
C1—S—C13	104.99 (7)	H10B—C10—H10C	109.5
C8—O3—C7	106.82 (11)	C9—C11—H11A	109.5
C8—C1—C2	107.62 (13)	C9—C11—H11B	109.5
C8—C1—S	126.33 (11)	H11A—C11—H11B	109.5
C2—C1—S	125.97 (11)	C9—C11—H11C	109.5
C7—C2—C3	118.96 (12)	H11A—C11—H11C	109.5
C7—C2—C1	104.63 (12)	H11B—C11—H11C	109.5
C3—C2—C1	136.39 (13)	C8—C12—H12A	109.5
C4—C3—C2	119.04 (13)	C8—C12—H12B	109.5
C4—C3—H3	120.5	H12A—C12—H12B	109.5
C2—C3—H3	120.5	C8—C12—H12C	109.5
C3—C4—C5	119.64 (13)	H12A—C12—H12C	109.5
C3—C4—C9	119.80 (13)	H12B—C12—H12C	109.5
C5—C4—C9	120.53 (13)	C14—C13—C18	121.08 (14)
C6—C5—C4	122.53 (13)	C14—C13—S	119.19 (11)
C6—C5—H5	118.7	C18—C13—S	119.73 (11)
C4—C5—H5	118.7	C15—C14—C13	119.29 (14)
C7—C6—C5	115.82 (13)	C15—C14—H14	120.4
C7—C6—H6	122.1	C13—C14—H14	120.4
C5—C6—H6	122.1	C16—C15—C14	118.36 (14)
C6—C7—O3	125.53 (13)	C16—C15—H15	120.8
C6—C7—C2	124.01 (13)	C14—C15—H15	120.8
O3—C7—C2	110.45 (12)	F—C16—C17	118.17 (14)
C1—C8—O3	110.44 (13)	F—C16—C15	118.35 (14)
C1—C8—C12	134.67 (15)	C17—C16—C15	123.48 (14)
O3—C8—C12	114.75 (13)	C16—C17—C18	118.29 (14)
C4—C9—C10	110.85 (14)	C16—C17—H17	120.9
C4—C9—C11	112.42 (13)	C18—C17—H17	120.9
C10—C9—C11	110.99 (15)	C17—C18—C13	119.49 (14)
C4—C9—H9	107.4	C17—C18—H18	120.3
C10—C9—H9	107.4	C13—C18—H18	120.3
C11—C9—H9	107.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2ⁱ	0.95	2.51	3.401 (2)	155
C10—H10B···Cg1ⁱⁱ	0.98	2.86	3.561 (2)	120
C11—H11B···Cg2ⁱⁱ	0.98	2.91	3.670 (2)	135
C17—H17···Cg2ⁱⁱⁱ	0.95	2.89	3.528 (2)	147

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇FO₃S
M_r	332.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	175
a, b, c (Å)	10.9434 (6), 11.3395 (6), 13.0988 (7)
β (°)	100.252 (3)
V (Å³)	1599.51 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.41 × 0.29 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.669, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	14304, 3655, 3109
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.108, 1.02
No. of reflections	3655
No. of parameters	212
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.37

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2ⁱ	0.95	2.51	3.401 (2)	155.4
C10—H10B···Cg1ⁱⁱ	0.98	2.86	3.561 (2)	120.0
C11—H11B···Cg2ⁱⁱ	0.98	2.91	3.670 (2)	134.7
C17—H17···Cg2ⁱⁱⁱ	0.95	2.89	3.528 (2)	146.8

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

References

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