5-Bromo-2,4,6-trimethyl-3-(3-methyl­phenyl­sulfin­yl)-1-benzo­furan

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

doi:10.1107/S1600536814005352

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 4| April 2014| Page o435

doi:10.1107/S1600536814005352

Open

access

5-Bromo-2,4,6-trimethyl-3-(3-methylphenylsulfinyl)-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 6 March 2014; accepted 8 March 2014; online 15 March 2014)

In the title compound, C₁₈H₁₇BrO₂S, the dihedral angle between the mean plane of the benzofuran ring system and the benzene ring is 68.58 (4)°. In the crystal, molecules are linked via pairs of C—H⋯O hydrogen bonds into inversion dimers. These dimers are linked by C—H⋯O hydrogen bonds and π–π interactions between the benzene rings of neighbouring molecules [centroid–centroid distance = 3.783 (1) Å], forming a three-dimensional network. In addition, the stacked molecules exhibit inversion-related S⋯O contacts [3.153 (1) Å] involving the sulfinyl groups.

CCDC reference: 990682

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2008 , 2011 ). For details of sulfinyl–sulfinyl interactions, see: Choi et al. (2013 ) and for a review of carbonyl–carbonyl interactions, see: Allen et al. (1998 ).

Experimental

Crystal data

C₁₈H₁₇BrO₂S
M_r = 377.29
Triclinic, $[P \overline 1]$
a = 6.2336 (1) Å
b = 11.0353 (2) Å
c = 12.9149 (2) Å
α = 69.384 (1)°
β = 76.421 (1)°
γ = 76.799 (1)°
V = 797.84 (2) Å³
Z = 2
Mo Kα radiation
μ = 2.71 mm⁻¹
T = 173 K
0.35 × 0.34 × 0.28 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.462, T_max = 0.746
14962 measured reflections
4023 independent reflections
3702 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.070
S = 1.06
4023 reflections
203 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1ⁱ	0.95	2.50	3.4478 (19)	172
C11—H11A⋯O2ⁱⁱ	0.98	2.36	3.244 (2)	150
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x-1, y, z.

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 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 990682

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814005352/bx2455sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814005352/bx2455Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814005352/bx2455Isup3.cml

checkCIF report

Comment top

As a part of our continuing study of 5-bromo-2,4,6-trimethyl-1-benzofuran derivatives containing phenylsulfinyl (Choi et al., 2008) and 4-fluorophenylsulfinyl (Choi et al., 2011) substituents in the 3-position, we report herein on the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.027 (1) Å from the least-squares plane defined by the nine constituent atoms. The 3-methylphenyl ring is essentially planar, with a mean deviation of 0.011 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 3-methylphenyl ring is 68.58 (4)°.

In the crystal structure (Fig. 2), molecules are linked via pairs of C–H···O hydrogen bonds into inversion dimers (Table 1). These dimers are further packed by C—H···O hydrogen bonds (Table 1) and π···π interactions between the benzene rings of neighbouring molecules, with a Cg1···Cg1^iv distance of 3.783 (1) Å and an interplanar distance of 3.402 (1) Å resulting in a slippage of 1.655 (1) Å (Cg1 is the centroid of the C2–C7 benzene ring), forming a three-dimensional network. In addition, the crystal packing (Fig. 2) exhibits a sulfinyl–sulfinyl interaction (Choi et al., 2013) interpreted as similar to a type II carbonyl–carbonyl interaction (Allen et al. 1998), with S1···O2ⁱⁱⁱ and O2ⁱⁱⁱ···S1 distance of 3.153 (1) Å.

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2008, 2011). For details of sulfinyl–sulfinyl interactions, see: Choi et al. (2013) and for a review of carbonyl–carbonyl interactions, see: Allen et al. (1998).

Experimental top

3-Chloroperoxybenzoic acid (77%, 269 mg, 1.2 mmol) was added in small portions to a stirred solution of 5-bromo-2,4,6-trimethyl-3-(3-methylphenylsulfanyl)-1-benzofuran (397 mg, 1.1 mmol) in dichloromethane (35 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 72%, m.p. 469–470 K; R_f = 0.52 (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.

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 molecule with the atom numbering scheme The displacement ellipsoids are drawn at the 50% probability level. The hydrogen atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the C—H···O, π···π 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) - x, - y + 1, - z + 1; (ii) x - 1, y, z; (iii) - x + 2, - y + 1, - z; (iv) - x + 1, -y + 1, - z + 1; (v) x + 1, y, z.]

5-Bromo-2,4,6-trimethyl-3-(3-methylphenylsulfinyl)-1-benzofuran top

Crystal data top

C₁₈H₁₇BrO₂S	Z = 2
M_r = 377.29	F(000) = 384
Triclinic, P1	D_x = 1.570 Mg m⁻³
Hall symbol: -P 1	Melting point = 469–470 K
a = 6.2336 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.0353 (2) Å	Cell parameters from 8866 reflections
c = 12.9149 (2) Å	θ = 3.0–28.4°
α = 69.384 (1)°	µ = 2.71 mm⁻¹
β = 76.421 (1)°	T = 173 K
γ = 76.799 (1)°	Block, colourless
V = 797.84 (2) Å³	0.35 × 0.34 × 0.28 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	4023 independent reflections
Radiation source: rotating anode	3702 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.031
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.4°, θ_min = 1.7°
ϕ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
T_min = 0.462, T_max = 0.746	l = −17→17
14962 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)] = 0.026	Hydrogen site location: difference Fourier map
wR(F²) = 0.070	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0354P)² + 0.3061P] where P = (F_o² + 2F_c²)/3
4023 reflections	(Δ/σ)_max = 0.001
203 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₈H₁₇BrO₂S	γ = 76.799 (1)°
M_r = 377.29	V = 797.84 (2) Å³
Triclinic, P1	Z = 2
a = 6.2336 (1) Å	Mo Kα radiation
b = 11.0353 (2) Å	µ = 2.71 mm⁻¹
c = 12.9149 (2) Å	T = 173 K
α = 69.384 (1)°	0.35 × 0.34 × 0.28 mm
β = 76.421 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4023 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3702 reflections with I > 2σ(I)
T_min = 0.462, T_max = 0.746	R_int = 0.031
14962 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.070	H-atom parameters constrained
S = 1.06	Δρ_max = 0.36 e Å⁻³
4023 reflections	Δρ_min = −0.49 e Å⁻³
203 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	0.62873 (3)	0.900826 (16)	0.403993 (14)	0.03223 (7)
S1	0.75692 (6)	0.51077 (3)	0.11568 (3)	0.01987 (9)
O1	0.27755 (19)	0.45708 (11)	0.37436 (9)	0.0241 (2)
O2	0.99335 (19)	0.51170 (11)	0.12084 (10)	0.0265 (2)
C1	0.5810 (3)	0.51004 (14)	0.24439 (12)	0.0196 (3)
C2	0.5305 (2)	0.59855 (14)	0.31119 (12)	0.0190 (3)
C3	0.6265 (3)	0.69926 (14)	0.31564 (12)	0.0195 (3)
C4	0.5100 (3)	0.76127 (15)	0.39418 (13)	0.0219 (3)
C5	0.3111 (3)	0.72874 (16)	0.46735 (13)	0.0244 (3)
C6	0.2268 (3)	0.62354 (17)	0.46533 (13)	0.0252 (3)
H6	0.0964	0.5954	0.5154	0.030*
C7	0.3399 (3)	0.56176 (15)	0.38791 (12)	0.0214 (3)
C8	0.4262 (3)	0.42809 (15)	0.28649 (12)	0.0221 (3)
C9	0.8457 (3)	0.73299 (16)	0.24263 (14)	0.0242 (3)
H9A	0.8171	0.8110	0.1782	0.036*
H9B	0.9253	0.6592	0.2159	0.036*
H9C	0.9372	0.7506	0.2863	0.036*
C10	0.1860 (3)	0.80420 (19)	0.54665 (16)	0.0341 (4)
H10A	0.0587	0.7619	0.5938	0.051*
H10B	0.1318	0.8943	0.5033	0.051*
H10C	0.2863	0.8054	0.5943	0.051*
C11	0.3854 (3)	0.31944 (16)	0.25548 (14)	0.0270 (3)
H11A	0.2470	0.3462	0.2240	0.041*
H11B	0.3713	0.2422	0.3224	0.041*
H11C	0.5108	0.2979	0.1995	0.041*
C12	0.6482 (3)	0.67448 (14)	0.03546 (12)	0.0198 (3)
C13	0.7999 (3)	0.75067 (15)	−0.04158 (12)	0.0225 (3)
H13	0.9557	0.7183	−0.0474	0.027*
C14	0.7230 (3)	0.87472 (16)	−0.11039 (14)	0.0275 (3)
C15	0.4952 (3)	0.92001 (17)	−0.09772 (15)	0.0329 (4)
H15	0.4411	1.0057	−0.1425	0.039*
C16	0.3449 (3)	0.84324 (19)	−0.02136 (15)	0.0337 (4)
H16	0.1893	0.8765	−0.0144	0.040*
C17	0.4195 (3)	0.71802 (17)	0.04509 (14)	0.0272 (3)
H17	0.3168	0.6635	0.0959	0.033*
C18	0.8835 (4)	0.9564 (2)	−0.19860 (17)	0.0443 (5)
H18A	0.8480	0.9733	−0.2729	0.066*
H18B	1.0366	0.9092	−0.1953	0.066*
H18C	0.8703	1.0399	−0.1850	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.04364 (12)	0.02725 (10)	0.03175 (10)	−0.01115 (8)	−0.00252 (8)	−0.01557 (7)
S1	0.02068 (18)	0.01787 (17)	0.02010 (17)	−0.00149 (13)	−0.00020 (13)	−0.00790 (13)
O1	0.0248 (6)	0.0267 (6)	0.0223 (5)	−0.0103 (5)	0.0007 (4)	−0.0087 (4)
O2	0.0194 (5)	0.0287 (6)	0.0292 (6)	0.0009 (4)	−0.0019 (4)	−0.0109 (5)
C1	0.0212 (7)	0.0183 (6)	0.0185 (6)	−0.0026 (5)	−0.0023 (5)	−0.0058 (5)
C2	0.0199 (7)	0.0189 (7)	0.0174 (6)	−0.0019 (5)	−0.0029 (5)	−0.0054 (5)
C3	0.0205 (7)	0.0181 (6)	0.0187 (6)	−0.0028 (5)	−0.0033 (5)	−0.0047 (5)
C4	0.0260 (8)	0.0195 (7)	0.0216 (7)	−0.0031 (6)	−0.0054 (6)	−0.0076 (6)
C5	0.0247 (8)	0.0268 (8)	0.0220 (7)	0.0008 (6)	−0.0034 (6)	−0.0113 (6)
C6	0.0215 (7)	0.0319 (8)	0.0213 (7)	−0.0058 (6)	0.0009 (6)	−0.0093 (6)
C7	0.0226 (7)	0.0215 (7)	0.0199 (7)	−0.0058 (6)	−0.0030 (6)	−0.0054 (5)
C8	0.0253 (8)	0.0212 (7)	0.0190 (7)	−0.0041 (6)	−0.0039 (6)	−0.0052 (5)
C9	0.0231 (7)	0.0237 (7)	0.0269 (7)	−0.0071 (6)	0.0008 (6)	−0.0106 (6)
C10	0.0325 (9)	0.0390 (10)	0.0318 (9)	0.0002 (8)	0.0010 (7)	−0.0204 (8)
C11	0.0324 (9)	0.0236 (8)	0.0282 (8)	−0.0094 (7)	−0.0055 (7)	−0.0085 (6)
C12	0.0223 (7)	0.0191 (7)	0.0180 (6)	−0.0024 (6)	−0.0027 (5)	−0.0069 (5)
C13	0.0242 (8)	0.0235 (7)	0.0213 (7)	−0.0064 (6)	−0.0022 (6)	−0.0084 (6)
C14	0.0363 (9)	0.0243 (8)	0.0239 (7)	−0.0107 (7)	−0.0056 (7)	−0.0061 (6)
C15	0.0436 (11)	0.0230 (8)	0.0299 (8)	0.0011 (7)	−0.0140 (8)	−0.0047 (6)
C16	0.0266 (9)	0.0370 (10)	0.0324 (9)	0.0061 (7)	−0.0082 (7)	−0.0097 (7)
C17	0.0226 (8)	0.0304 (8)	0.0253 (8)	−0.0026 (6)	−0.0018 (6)	−0.0071 (6)
C18	0.0531 (13)	0.0348 (10)	0.0388 (10)	−0.0213 (9)	−0.0083 (9)	0.0051 (8)

Geometric parameters (Å, º) top

Br1—C4	1.9073 (15)	C9—H9C	0.9800
S1—O2	1.4934 (12)	C10—H10A	0.9800
S1—C1	1.7619 (15)	C10—H10B	0.9800
S1—C12	1.8024 (15)	C10—H10C	0.9800
S1—O2ⁱ	3.1527 (12)	C11—H11A	0.9800
O1—C8	1.3694 (19)	C11—H11B	0.9800
O1—C7	1.3770 (18)	C11—H11C	0.9800
C1—C8	1.361 (2)	C12—C13	1.387 (2)
C1—C2	1.457 (2)	C12—C17	1.387 (2)
C2—C7	1.393 (2)	C13—C14	1.392 (2)
C2—C3	1.401 (2)	C13—H13	0.9500
C3—C4	1.393 (2)	C14—C15	1.385 (3)
C3—C9	1.508 (2)	C14—C18	1.505 (2)
C4—C5	1.405 (2)	C15—C16	1.381 (3)
C5—C6	1.390 (2)	C15—H15	0.9500
C5—C10	1.510 (2)	C16—C17	1.386 (2)
C6—C7	1.375 (2)	C16—H16	0.9500
C6—H6	0.9500	C17—H17	0.9500
C8—C11	1.479 (2)	C18—H18A	0.9800
C9—H9A	0.9800	C18—H18B	0.9800
C9—H9B	0.9800	C18—H18C	0.9800

O2—S1—C1	111.08 (7)	C5—C10—H10A	109.5
O2—S1—C12	106.70 (7)	C5—C10—H10B	109.5
C1—S1—C12	96.91 (7)	H10A—C10—H10B	109.5
O2—S1—O2ⁱ	78.25 (6)	C5—C10—H10C	109.5
C1—S1—O2ⁱ	169.73 (6)	H10A—C10—H10C	109.5
C12—S1—O2ⁱ	83.97 (5)	H10B—C10—H10C	109.5
C8—O1—C7	106.60 (12)	C8—C11—H11A	109.5
C8—C1—C2	107.12 (13)	C8—C11—H11B	109.5
C8—C1—S1	118.68 (12)	H11A—C11—H11B	109.5
C2—C1—S1	133.04 (11)	C8—C11—H11C	109.5
C7—C2—C3	119.45 (14)	H11A—C11—H11C	109.5
C7—C2—C1	104.27 (13)	H11B—C11—H11C	109.5
C3—C2—C1	136.25 (14)	C13—C12—C17	121.63 (14)
C4—C3—C2	115.39 (14)	C13—C12—S1	117.57 (12)
C4—C3—C9	123.20 (13)	C17—C12—S1	120.62 (12)
C2—C3—C9	121.37 (13)	C12—C13—C14	119.71 (15)
C3—C4—C5	125.00 (14)	C12—C13—H13	120.1
C3—C4—Br1	117.82 (11)	C14—C13—H13	120.1
C5—C4—Br1	117.18 (11)	C15—C14—C13	118.57 (16)
C6—C5—C4	118.23 (14)	C15—C14—C18	120.73 (16)
C6—C5—C10	119.23 (15)	C13—C14—C18	120.69 (17)
C4—C5—C10	122.54 (15)	C16—C15—C14	121.38 (16)
C7—C6—C5	117.29 (14)	C16—C15—H15	119.3
C7—C6—H6	121.4	C14—C15—H15	119.3
C5—C6—H6	121.4	C15—C16—C17	120.44 (17)
C6—C7—O1	124.56 (14)	C15—C16—H16	119.8
C6—C7—C2	124.45 (14)	C17—C16—H16	119.8
O1—C7—C2	110.98 (13)	C16—C17—C12	118.19 (16)
C1—C8—O1	110.99 (13)	C16—C17—H17	120.9
C1—C8—C11	133.49 (15)	C12—C17—H17	120.9
O1—C8—C11	115.50 (14)	C14—C18—H18A	109.5
C3—C9—H9A	109.5	C14—C18—H18B	109.5
C3—C9—H9B	109.5	H18A—C18—H18B	109.5
H9A—C9—H9B	109.5	C14—C18—H18C	109.5
C3—C9—H9C	109.5	H18A—C18—H18C	109.5
H9A—C9—H9C	109.5	H18B—C18—H18C	109.5
H9B—C9—H9C	109.5

O2—S1—C1—C8	−136.06 (12)	C8—O1—C7—C2	−1.35 (16)
C12—S1—C1—C8	113.02 (13)	C3—C2—C7—C6	4.5 (2)
O2—S1—C1—C2	58.06 (17)	C1—C2—C7—C6	−177.07 (15)
C12—S1—C1—C2	−52.85 (16)	C3—C2—C7—O1	−176.74 (13)
C8—C1—C2—C7	−1.46 (16)	C1—C2—C7—O1	1.73 (16)
S1—C1—C2—C7	165.60 (13)	C2—C1—C8—O1	0.71 (17)
C8—C1—C2—C3	176.62 (17)	S1—C1—C8—O1	−168.54 (10)
S1—C1—C2—C3	−16.3 (3)	C2—C1—C8—C11	179.18 (16)
C7—C2—C3—C4	−4.3 (2)	S1—C1—C8—C11	9.9 (2)
C1—C2—C3—C4	177.88 (16)	C7—O1—C8—C1	0.35 (17)
C7—C2—C3—C9	173.53 (14)	C7—O1—C8—C11	−178.42 (13)
C1—C2—C3—C9	−4.3 (3)	O2—S1—C12—C13	25.77 (14)
C2—C3—C4—C5	0.9 (2)	C1—S1—C12—C13	140.27 (12)
C9—C3—C4—C5	−176.88 (15)	O2—S1—C12—C17	−158.95 (13)
C2—C3—C4—Br1	−179.31 (10)	C1—S1—C12—C17	−44.45 (14)
C9—C3—C4—Br1	2.9 (2)	C17—C12—C13—C14	0.8 (2)
C3—C4—C5—C6	2.7 (2)	S1—C12—C13—C14	176.07 (12)
Br1—C4—C5—C6	−177.13 (12)	C12—C13—C14—C15	1.6 (2)
C3—C4—C5—C10	−176.77 (15)	C12—C13—C14—C18	−176.88 (16)
Br1—C4—C5—C10	3.4 (2)	C13—C14—C15—C16	−2.1 (3)
C4—C5—C6—C7	−2.7 (2)	C18—C14—C15—C16	176.39 (18)
C10—C5—C6—C7	176.80 (15)	C14—C15—C16—C17	0.1 (3)
C5—C6—C7—O1	−179.40 (14)	C15—C16—C17—C12	2.3 (3)
C5—C6—C7—C2	−0.8 (2)	C13—C12—C17—C16	−2.8 (2)
C8—O1—C7—C6	177.44 (15)	S1—C12—C17—C16	−177.85 (13)

Symmetry code: (i) −x+2, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱⁱ	0.95	2.50	3.4478 (19)	172
C11—H11A···O2ⁱⁱⁱ	0.98	2.36	3.244 (2)	150

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.95	2.50	3.4478 (19)	171.8
C11—H11A···O2ⁱⁱ	0.98	2.36	3.244 (2)	149.8

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

References

Allen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320–329. Web of Science CrossRef CAS IUCr Journals Google Scholar
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. (2013). Acta Cryst. E69, o820. CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o1826. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o471. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 4| April 2014| Page o435

doi:10.1107/S1600536814005352

Open

access