3-(3-Chloro­phenyl­sulfin­yl)-2,5,7-trimethyl-1-benzofuran

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

doi:10.1107/S1600536812008537

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o943

doi:10.1107/S1600536812008537

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3-(3-Chlorophenylsulfinyl)-2,5,7-trimethyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo ^a 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 22 February 2012; accepted 26 February 2012; online 3 March 2012)

In the title compound, C₁₇H₁₅ClO₂S, the 3-chlorophenyl ring makes a dihedral angle of 84.48 (4)° with the mean plane [r.m.s. deviation = 0.004 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O, C—H⋯π and C—S⋯π [3.414 (2) Å] interactions. The crystal structure also exhibits weak π–π interactions between the furan rings of neighbouring molecules [centroid–centroid distance = 3.826 (2), interplanar distance = 3.447 (2) and slippage = 1.660 (2) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010 , 2011 , 2012 ).

Experimental

Crystal data

C₁₇H₁₅ClO₂S
M_r = 318.80
Triclinic, $[P \overline 1]$
a = 6.1701 (1) Å
b = 11.6670 (2) Å
c = 12.1123 (3) Å
α = 112.965 (1)°
β = 99.114 (1)°
γ = 103.698 (1)°
V = 748.70 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 173 K
0.20 × 0.19 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.926, T_max = 0.934
13458 measured reflections
3463 independent reflections
3136 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.096
S = 1.07
3463 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2ⁱ	0.95	2.55	3.2960 (16)	136
C11—H11B⋯Cg1ⁱⁱ	0.98	2.88	3.703	143
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) -x+1, -y+1, -z+1.

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: 10.1107/S1600536812008537/lr2053sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812008537/lr2053Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812008537/lr2053Isup3.cml

checkCIF report

Comment top

As a part of our ongoing study of 2,5,7-trimethyl-1-benzofuran derivatives containing 3-(4-chlorophenylsulfinyl) (Choi et al.,2010), 3-(3-fluorophenylsulfinyl)(Choi et al., 2011) and 3-(4-bromophenylsulfinyl)(Choi et al., 2012) substituents, 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 0.004 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 3-chlorobenzene ring and the mean plane of the benzofuran fragment is 84.48 (4)°. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O and C—H···π interactions (Table 1, Cg1 is the centroid of the C2–C7 benzene ring), and by intermolecular S···π interactions between the sulfur atom and the 3-chlorobenzene ring of an adjacent molecule, with S1···Cg2ⁱⁱⁱ being 3.414 (2) Å (Cg2 is the centroid of the C12–C17 3-chlorobenzene ring). Additionally, the crystal packing (Fig. 2) exhibits weak slipped π–π interactions between the furan rings of neighbouring molecules, with a with a Cg3···Cg3ⁱⁱ distance of 3.826 (2) Å and an interplanar distance of 3.447 (2) Å resulting in a slippage of 1.660 (2) Å (Cg3 is the centroid of the C1/C2/C7/O1/C8 furan ring).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2010, 2011, 2012).

Experimental top

77% 3-Chloroperoxybenzoic acid (247 mg, 1.1 mmol) was added in small portions to a stirred solution of 3-(3-chlorophenylsulfanyl)-2,5,7-trimethyl-1-benzofuran (303 mg, 1.0 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4h, 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 78%, m.p. 428–429 K; R_f = 0.49 (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 ethyl acetate at room temperature.

Structure description top

For background information and the crystal structures of related compounds, see: Choi et al. (2010, 2011, 2012).

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. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view of the C—H···O, C—H···π, C—S···π and π–π 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) - x + 2, - y + 1, - z + 2 (ii) - x + 1, - y + 1, - z + 1 (iii) - x + 1, - y + 1 , - z + 2

3-(3-Chlorophenylsulfinyl)-2,5,7-trimethyl-1-benzofuran top

Crystal data top

C₁₇H₁₅ClO₂S	Z = 2
M_r = 318.80	F(000) = 332
Triclinic, P1	D_x = 1.414 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.1701 (1) Å	Cell parameters from 7460 reflections
b = 11.6670 (2) Å	θ = 3.3–27.6°
c = 12.1123 (3) Å	µ = 0.40 mm⁻¹
α = 112.965 (1)°	T = 173 K
β = 99.114 (1)°	Block, colourless
γ = 103.698 (1)°	0.20 × 0.19 × 0.18 mm
V = 748.70 (3) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3463 independent reflections
Radiation source: rotating anode	3136 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.023
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.6°, θ_min = 1.9°
φ and ω scans	h = −7→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −15→15
T_min = 0.926, T_max = 0.934	l = −14→15
13458 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)] = 0.034	Hydrogen site location: difference Fourier map
wR(F²) = 0.096	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0531P)² + 0.2623P] where P = (F_o² + 2F_c²)/3
3463 reflections	(Δ/σ)_max = 0.001
193 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₇H₁₅ClO₂S	γ = 103.698 (1)°
M_r = 318.80	V = 748.70 (3) Å³
Triclinic, P1	Z = 2
a = 6.1701 (1) Å	Mo Kα radiation
b = 11.6670 (2) Å	µ = 0.40 mm⁻¹
c = 12.1123 (3) Å	T = 173 K
α = 112.965 (1)°	0.20 × 0.19 × 0.18 mm
β = 99.114 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3463 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3136 reflections with I > 2σ(I)
T_min = 0.926, T_max = 0.934	R_int = 0.023
13458 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.07	Δρ_max = 0.29 e Å⁻³
3463 reflections	Δρ_min = −0.30 e Å⁻³
193 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
Cl1	0.71046 (7)	0.15422 (4)	1.01673 (4)	0.03980 (13)
S1	0.62148 (6)	0.50385 (3)	0.83504 (3)	0.02455 (11)
O1	0.24560 (17)	0.38716 (10)	0.49273 (9)	0.0276 (2)
O2	0.87230 (17)	0.51728 (11)	0.85352 (10)	0.0334 (2)
C1	0.4848 (2)	0.42875 (13)	0.67382 (12)	0.0240 (3)
C2	0.5205 (2)	0.32070 (13)	0.57651 (12)	0.0236 (3)
C3	0.6609 (2)	0.24231 (14)	0.57050 (14)	0.0286 (3)
H3	0.7670	0.2559	0.6440	0.034*
C4	0.6425 (3)	0.14386 (15)	0.45483 (15)	0.0328 (3)
C5	0.4846 (3)	0.12593 (15)	0.34719 (14)	0.0338 (3)
H5	0.4745	0.0580	0.2689	0.041*
C6	0.3429 (3)	0.20295 (15)	0.34993 (13)	0.0303 (3)
C7	0.3683 (2)	0.29925 (14)	0.46700 (13)	0.0248 (3)
C8	0.3205 (2)	0.46457 (14)	0.61921 (13)	0.0253 (3)
C9	0.7918 (3)	0.05666 (19)	0.44441 (19)	0.0455 (4)
H9A	0.9141	0.0814	0.4073	0.068*
H9B	0.6954	−0.0356	0.3914	0.068*
H9C	0.8628	0.0675	0.5277	0.068*
C10	0.1747 (3)	0.18530 (18)	0.23546 (15)	0.0428 (4)
H10A	0.0170	0.1662	0.2447	0.064*
H10B	0.1809	0.1119	0.1618	0.064*
H10C	0.2166	0.2663	0.2252	0.064*
C11	0.2052 (3)	0.56436 (16)	0.66873 (15)	0.0338 (3)
H11A	0.0457	0.5201	0.6645	0.051*
H11B	0.2023	0.6129	0.6186	0.051*
H11C	0.2914	0.6259	0.7557	0.051*
C12	0.4908 (2)	0.36608 (13)	0.86309 (12)	0.0234 (3)
C13	0.6366 (2)	0.31970 (13)	0.92070 (12)	0.0245 (3)
H13	0.8008	0.3577	0.9432	0.029*
C14	0.5339 (3)	0.21551 (14)	0.94437 (13)	0.0275 (3)
C15	0.2958 (3)	0.16024 (15)	0.91376 (14)	0.0335 (3)
H15	0.2296	0.0886	0.9305	0.040*
C16	0.1544 (3)	0.21071 (16)	0.85821 (15)	0.0361 (3)
H16	−0.0097	0.1734	0.8368	0.043*
C17	0.2507 (3)	0.31488 (15)	0.83378 (14)	0.0311 (3)
H17	0.1541	0.3508	0.7975	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0494 (2)	0.0350 (2)	0.0403 (2)	0.01686 (18)	0.00730 (17)	0.02221 (18)
S1	0.02701 (19)	0.02439 (18)	0.01981 (17)	0.00680 (13)	0.00449 (12)	0.00919 (13)
O1	0.0276 (5)	0.0334 (5)	0.0249 (5)	0.0140 (4)	0.0052 (4)	0.0146 (4)
O2	0.0237 (5)	0.0406 (6)	0.0315 (5)	0.0026 (4)	0.0024 (4)	0.0184 (5)
C1	0.0247 (6)	0.0269 (6)	0.0217 (6)	0.0098 (5)	0.0062 (5)	0.0114 (5)
C2	0.0233 (6)	0.0262 (7)	0.0222 (6)	0.0081 (5)	0.0066 (5)	0.0116 (5)
C3	0.0268 (7)	0.0320 (7)	0.0301 (7)	0.0133 (6)	0.0072 (5)	0.0152 (6)
C4	0.0341 (8)	0.0313 (7)	0.0379 (8)	0.0150 (6)	0.0150 (6)	0.0158 (6)
C5	0.0425 (9)	0.0281 (7)	0.0271 (7)	0.0111 (6)	0.0129 (6)	0.0076 (6)
C6	0.0328 (7)	0.0315 (7)	0.0232 (7)	0.0068 (6)	0.0056 (6)	0.0118 (6)
C7	0.0249 (6)	0.0271 (6)	0.0246 (6)	0.0097 (5)	0.0067 (5)	0.0131 (5)
C8	0.0267 (6)	0.0284 (7)	0.0247 (6)	0.0111 (5)	0.0089 (5)	0.0139 (5)
C9	0.0517 (10)	0.0430 (9)	0.0514 (10)	0.0295 (8)	0.0222 (8)	0.0195 (8)
C10	0.0516 (10)	0.0425 (9)	0.0239 (7)	0.0109 (8)	−0.0015 (7)	0.0117 (7)
C11	0.0350 (8)	0.0372 (8)	0.0380 (8)	0.0207 (7)	0.0144 (6)	0.0186 (7)
C12	0.0257 (6)	0.0246 (6)	0.0180 (6)	0.0077 (5)	0.0064 (5)	0.0080 (5)
C13	0.0244 (6)	0.0257 (6)	0.0210 (6)	0.0082 (5)	0.0056 (5)	0.0084 (5)
C14	0.0355 (7)	0.0254 (6)	0.0211 (6)	0.0117 (6)	0.0073 (5)	0.0092 (5)
C15	0.0382 (8)	0.0283 (7)	0.0310 (7)	0.0046 (6)	0.0127 (6)	0.0129 (6)
C16	0.0251 (7)	0.0394 (8)	0.0380 (8)	0.0037 (6)	0.0094 (6)	0.0154 (7)
C17	0.0249 (7)	0.0383 (8)	0.0292 (7)	0.0096 (6)	0.0056 (5)	0.0154 (6)

Geometric parameters (Å, º) top

Cl1—C14	1.7385 (15)	C9—H9A	0.9800
S1—O2	1.4892 (11)	C9—H9B	0.9800
S1—C1	1.7564 (14)	C9—H9C	0.9800
S1—C12	1.8023 (14)	C10—H10A	0.9800
O1—C8	1.3692 (17)	C10—H10B	0.9800
O1—C7	1.3839 (17)	C10—H10C	0.9800
C1—C8	1.3577 (19)	C11—H11A	0.9800
C1—C2	1.4427 (18)	C11—H11B	0.9800
C2—C3	1.3910 (19)	C11—H11C	0.9800
C2—C7	1.3924 (18)	C12—C13	1.3840 (19)
C3—C4	1.388 (2)	C12—C17	1.3880 (19)
C3—H3	0.9500	C13—C14	1.388 (2)
C4—C5	1.407 (2)	C13—H13	0.9500
C4—C9	1.510 (2)	C14—C15	1.379 (2)
C5—C6	1.390 (2)	C15—C16	1.388 (2)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.379 (2)	C16—C17	1.383 (2)
C6—C10	1.504 (2)	C16—H16	0.9500
C8—C11	1.485 (2)	C17—H17	0.9500

O2—S1—C1	108.33 (6)	H9A—C9—H9C	109.5
O2—S1—C12	105.99 (6)	H9B—C9—H9C	109.5
C1—S1—C12	96.82 (6)	C6—C10—H10A	109.5
C8—O1—C7	106.60 (10)	C6—C10—H10B	109.5
C8—C1—C2	107.66 (12)	H10A—C10—H10B	109.5
C8—C1—S1	124.30 (11)	C6—C10—H10C	109.5
C2—C1—S1	128.05 (10)	H10A—C10—H10C	109.5
C3—C2—C7	119.35 (13)	H10B—C10—H10C	109.5
C3—C2—C1	136.00 (13)	C8—C11—H11A	109.5
C7—C2—C1	104.65 (12)	C8—C11—H11B	109.5
C4—C3—C2	118.57 (13)	H11A—C11—H11B	109.5
C4—C3—H3	120.7	C8—C11—H11C	109.5
C2—C3—H3	120.7	H11A—C11—H11C	109.5
C3—C4—C5	119.72 (14)	H11B—C11—H11C	109.5
C3—C4—C9	120.17 (15)	C13—C12—C17	121.99 (13)
C5—C4—C9	120.11 (15)	C13—C12—S1	118.00 (10)
C6—C5—C4	123.12 (14)	C17—C12—S1	119.90 (11)
C6—C5—H5	118.4	C12—C13—C14	117.46 (13)
C4—C5—H5	118.4	C12—C13—H13	121.3
C7—C6—C5	114.77 (13)	C14—C13—H13	121.3
C7—C6—C10	121.63 (15)	C15—C14—C13	122.02 (14)
C5—C6—C10	123.60 (15)	C15—C14—Cl1	118.97 (12)
C6—C7—O1	125.10 (13)	C13—C14—Cl1	119.01 (11)
C6—C7—C2	124.46 (13)	C14—C15—C16	119.08 (14)
O1—C7—C2	110.43 (12)	C14—C15—H15	120.5
C1—C8—O1	110.66 (12)	C16—C15—H15	120.5
C1—C8—C11	133.42 (13)	C17—C16—C15	120.50 (14)
O1—C8—C11	115.88 (12)	C17—C16—H16	119.8
C4—C9—H9A	109.5	C15—C16—H16	119.8
C4—C9—H9B	109.5	C16—C17—C12	118.90 (14)
H9A—C9—H9B	109.5	C16—C17—H17	120.6
C4—C9—H9C	109.5	C12—C17—H17	120.6

O2—S1—C1—C8	−139.54 (12)	C1—C2—C7—C6	−179.32 (13)
C12—S1—C1—C8	111.08 (13)	C3—C2—C7—O1	−179.80 (12)
O2—S1—C1—C2	40.95 (14)	C1—C2—C7—O1	0.13 (15)
C12—S1—C1—C2	−68.43 (13)	C2—C1—C8—O1	0.15 (16)
C8—C1—C2—C3	179.75 (16)	S1—C1—C8—O1	−179.45 (10)
S1—C1—C2—C3	−0.7 (2)	C2—C1—C8—C11	177.69 (15)
C8—C1—C2—C7	−0.17 (15)	S1—C1—C8—C11	−1.9 (2)
S1—C1—C2—C7	179.41 (11)	C7—O1—C8—C1	−0.07 (15)
C7—C2—C3—C4	−0.6 (2)	C7—O1—C8—C11	−178.08 (12)
C1—C2—C3—C4	179.46 (15)	O2—S1—C12—C13	14.09 (12)
C2—C3—C4—C5	0.2 (2)	C1—S1—C12—C13	125.42 (11)
C2—C3—C4—C9	−179.98 (15)	O2—S1—C12—C17	−169.67 (11)
C3—C4—C5—C6	0.1 (2)	C1—S1—C12—C17	−58.34 (12)
C9—C4—C5—C6	−179.69 (15)	C17—C12—C13—C14	2.4 (2)
C4—C5—C6—C7	0.0 (2)	S1—C12—C13—C14	178.57 (10)
C4—C5—C6—C10	179.59 (16)	C12—C13—C14—C15	−0.8 (2)
C5—C6—C7—O1	−179.78 (13)	C12—C13—C14—Cl1	−179.94 (10)
C10—C6—C7—O1	0.6 (2)	C13—C14—C15—C16	−0.4 (2)
C5—C6—C7—C2	−0.4 (2)	Cl1—C14—C15—C16	178.74 (12)
C10—C6—C7—C2	179.97 (14)	C14—C15—C16—C17	0.0 (2)
C8—O1—C7—C6	179.40 (13)	C15—C16—C17—C12	1.5 (2)
C8—O1—C7—C2	−0.04 (15)	C13—C12—C17—C16	−2.7 (2)
C3—C2—C7—C6	0.8 (2)	S1—C12—C17—C16	−178.83 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	0.95	2.55	3.2960 (16)	136
C11—H11B···Cg1ⁱⁱ	0.98	2.88	3.703	143

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅ClO₂S
M_r	318.80
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	6.1701 (1), 11.6670 (2), 12.1123 (3)
α, β, γ (°)	112.965 (1), 99.114 (1), 103.698 (1)
V (Å³)	748.70 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.20 × 0.19 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.926, 0.934
No. of measured, independent and observed [I > 2σ(I)] reflections	13458, 3463, 3136
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.096, 1.07
No. of reflections	3463
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.30

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

Cg1 is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	0.95	2.55	3.2960 (16)	135.8
C11—H11B···Cg1ⁱⁱ	0.98	2.88	3.703	142.9

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

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o482. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o2325. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o1468. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 4| April 2012| Page o943

doi:10.1107/S1600536812008537

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