5-Bromo-3-ethyl­sulfinyl-7-methyl-2-(4-methyl­phen­yl)-1-benzo­furan

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

doi:10.1107/S1600536814005844

organic compounds

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ISSN: 2056-9890

Volume 70| Part 4| April 2014| Page o461

doi:10.1107/S1600536814005844

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5-Bromo-3-ethylsulfinyl-7-methyl-2-(4-methylphenyl)-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 14 March 2014; accepted 16 March 2014; online 22 March 2014)

In the title compound, C₁₈H₁₇BrO₂S, the dihedral angle between the mean planes of the benzofuran and 4-methylphenyl rings is 14.54 (5)°. In the crystal, molecules are linked via pairs of π–π interactions between the benzene and 4-methylphenyl rings, with centroid–centroid distances of 3.811 (3) and 3.755 (3) Å. A similar interaction is found between the furan and 4-methylphenyl rings, with a centroid–centroid distance of 3.866 (3) Å between neighbouring molecules. The molecules are stacked along the a-axis direction. In addition, a short Br⋯O contact distance of 3.128 (2) Å is observed between inversion-related dimers.

CCDC reference: 992016

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010a ,b ). For a review of halogen bonding, see: Politzer et al. (2007 ). For π–π stacking in metal complexes with aromatic nitrogen ligands, see: Janiak (2000 ).

Experimental

Crystal data

C₁₈H₁₇BrO₂S
M_r = 377.29
Triclinic, $[P \overline 1]$
a = 7.3921 (2) Å
b = 10.2909 (3) Å
c = 11.8701 (3) Å
α = 68.867 (1)°
β = 89.146 (1)°
γ = 71.361 (1)°
V = 792.91 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.73 mm⁻¹
T = 173 K
0.37 × 0.25 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.535, T_max = 0.746
13645 measured reflections
3457 independent reflections
3145 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.076
S = 1.04
3457 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.47 e Å⁻³

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: 992016

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814005844/fj2667sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814005844/fj2667Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814005844/fj2667Isup3.cml

checkCIF report

Comment top

As a part of our continuing study of 5-bromo-3-ethylsulfinyl-7-methyl-1-benzofuran derivatives containing 4-fluorophenyl (Choi et al., 2010a) and 4-chlorophenyl (Choi et al., 2010b) substituents in 2-position, we report here on the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran ring system is essentially planar, with a mean deviation of 0.017 (2) Å from the least-squares plane defined by the nine constituent atoms. The 4-methylphenyl ring is essentially planar, with a mean deviation of 0.004 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 4-methylphenyl ring is 14.54 (5)°.

In the crystal structure (Fig. 2), the molecules are linked via π–π interactions between the benzene and 4-methylphenyl rings, and the furan and 4-methylphenyl rings of neighbouring molecules. The molecules stack along the a-axis direction. The relevant centroid names of π–π stacking interactions are Cg1 for the benzene ring (C2–C7), Cg2 for the furan ring (C1/C2/C7/O1/O8) and Cg3 for the 4-methylphenyl ring (C10–C15). The centroid–centroid separations of Cg1···Cg3ⁱⁱ, Cg1···Cg3ⁱⁱⁱ and Cg2···Cg3ⁱⁱ are 3.811 (2), 3.755 (2) and 3.866 (2) Å, respectively. The symmetry codes are:(ii) -x + 1, -y + 1, -z + 1; (iii)-x + 2, -y + 1, -z + 1. Both interplanar angles between the rings (C2–C7) and (C10–C15)ⁱⁱ as well as (C2–C7) and (C10–C15)ⁱⁱⁱ, and (C1/C2/C7/O1/C8) and (C10–C15)ⁱⁱ equal to 13.90 (5)° and 15.66 (5)°, respectively. This angle is quite large for rings being in π-electron···π-electron interactions as it follows from the study by Janiak (2000) who investigated π–π stacking in metal complexes with aromatic nitrogen ligands. According to Fig. 8 of Janiak's study, the interplanar angles between the rings that are involved in π-electron···π-electron interactions are less than 10° in overwhelming majority of cases. In addition, Br···O halogen-bondings (Politzer et al., 2007) between the bromine atom and the oxygen atom of the S═O unit [Br1···O2ⁱ = 3.128 (2) Å C4—Br1···O2ⁱ = 164.97 (7)°, (symmetry code :(i) - x + 2, - y + 1, - z + 2)] are observed between inversion-related dimers.

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2010a,b). For a review of halogen bonding, see: Politzer et al. (2007). For π–π stacking in metal complexes with aromatic nitrogen ligands, see: Janiak (2000).

Experimental top

3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-bromo-3-ethylsulfanyl-7-methyl-2-(4-methylphenyl)-1-benzofuran (361 mg, 0.9 mmol) in dichloromethane (25 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, 1:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 419–420 K; R_f = 0.51 (hexane-ethyl acetate, 1:1 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 Br···O and π–π interactions (dotted lines) in the crystal structure of the title compound. The H-atoms were omitted for clarity. [Symmetry codes: (i)- x + 2, - y + 1, - z + 2; (ii) -x + 1, -y + 1, -z + 1; (iii) -x + 2, -y + 1, -z + 1.]

5-Bromo-3-ethylsulfinyl-7-methyl-2-(4-methylphenyl)-1-benzofuran top

Crystal data top

C₁₈H₁₇BrO₂S	Z = 2
M_r = 377.29	F(000) = 384
Triclinic, P1	D_x = 1.580 Mg m⁻³
Hall symbol: -P 1	Melting point = 420–419 K
a = 7.3921 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2909 (3) Å	Cell parameters from 8443 reflections
c = 11.8701 (3) Å	θ = 2.3–28.3°
α = 68.867 (1)°	µ = 2.73 mm⁻¹
β = 89.146 (1)°	T = 173 K
γ = 71.361 (1)°	Block, colourless
V = 792.91 (4) Å³	0.37 × 0.25 × 0.22 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3457 independent reflections
Radiation source: rotating anode	3145 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.035
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.0°, θ_min = 1.9°
ϕ and ω scans	h = −8→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→13
T_min = 0.535, T_max = 0.746	l = −15→15
13645 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) = 0.076	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0422P)² + 0.3263P] where P = (F_o² + 2F_c²)/3
3457 reflections	(Δ/σ)_max = 0.001
202 parameters	Δρ_max = 0.66 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₁₈H₁₇BrO₂S	γ = 71.361 (1)°
M_r = 377.29	V = 792.91 (4) Å³
Triclinic, P1	Z = 2
a = 7.3921 (2) Å	Mo Kα radiation
b = 10.2909 (3) Å	µ = 2.73 mm⁻¹
c = 11.8701 (3) Å	T = 173 K
α = 68.867 (1)°	0.37 × 0.25 × 0.22 mm
β = 89.146 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3457 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3145 reflections with I > 2σ(I)
T_min = 0.535, T_max = 0.746	R_int = 0.035
13645 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.076	H-atom parameters constrained
S = 1.04	Δρ_max = 0.66 e Å⁻³
3457 reflections	Δρ_min = −0.47 e Å⁻³
202 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	0.99213 (3)	0.28117 (2)	1.076443 (17)	0.03316 (9)
S1	0.64111 (7)	0.80626 (5)	0.58929 (4)	0.02572 (12)
O1	0.80567 (19)	0.41973 (14)	0.55125 (12)	0.0243 (3)
O2	0.7922 (2)	0.81341 (17)	0.66688 (15)	0.0380 (4)
C1	0.7074 (3)	0.6207 (2)	0.60113 (17)	0.0226 (4)
C2	0.7941 (3)	0.4927 (2)	0.71109 (17)	0.0232 (4)
C3	0.8306 (3)	0.4680 (2)	0.83342 (17)	0.0251 (4)
H3	0.7908	0.5463	0.8627	0.030*
C4	0.9278 (3)	0.3240 (2)	0.90957 (17)	0.0262 (4)
C5	0.9886 (3)	0.2066 (2)	0.86941 (18)	0.0269 (4)
H5	1.0556	0.1097	0.9262	0.032*
C6	0.9532 (3)	0.2284 (2)	0.74878 (18)	0.0252 (4)
C7	0.8532 (3)	0.3738 (2)	0.67370 (17)	0.0231 (4)
C8	0.7173 (3)	0.5711 (2)	0.50770 (17)	0.0231 (4)
C9	1.0208 (3)	0.1073 (2)	0.70051 (19)	0.0314 (4)
H9A	0.9108	0.0820	0.6816	0.047*
H9B	1.1140	0.0198	0.7618	0.047*
H9C	1.0816	0.1406	0.6266	0.047*
C10	0.6536 (3)	0.6380 (2)	0.37788 (17)	0.0236 (4)
C11	0.5193 (3)	0.7799 (2)	0.32352 (18)	0.0273 (4)
H11	0.4689	0.8370	0.3715	0.033*
C12	0.4589 (3)	0.8382 (2)	0.20024 (18)	0.0302 (4)
H12	0.3686	0.9355	0.1646	0.036*
C13	0.5276 (3)	0.7571 (2)	0.12746 (18)	0.0305 (4)
C14	0.6616 (3)	0.6152 (2)	0.18236 (19)	0.0309 (4)
H14	0.7102	0.5578	0.1345	0.037*
C15	0.7248 (3)	0.5567 (2)	0.30458 (18)	0.0273 (4)
H15	0.8175	0.4604	0.3395	0.033*
C16	0.4606 (3)	0.8183 (3)	−0.00608 (19)	0.0407 (5)
H16A	0.3793	0.7662	−0.0213	0.061*
H16B	0.5721	0.8047	−0.0517	0.061*
H16C	0.3865	0.9241	−0.0324	0.061*
C17	0.4326 (3)	0.8128 (2)	0.67180 (19)	0.0314 (5)
H17A	0.4619	0.7210	0.7452	0.038*
H17B	0.4015	0.8974	0.6986	0.038*
C18	0.2603 (3)	0.8292 (2)	0.5931 (2)	0.0336 (5)
H18A	0.2232	0.9248	0.5247	0.050*
H18B	0.1527	0.8241	0.6418	0.050*
H18C	0.2939	0.7492	0.5621	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03870 (14)	0.03266 (13)	0.02694 (12)	−0.01276 (9)	−0.00261 (8)	−0.00897 (9)
S1	0.0267 (2)	0.0211 (2)	0.0298 (2)	−0.00751 (18)	0.00028 (19)	−0.01041 (18)
O1	0.0245 (7)	0.0218 (6)	0.0263 (6)	−0.0059 (5)	0.0029 (5)	−0.0104 (5)
O2	0.0368 (9)	0.0364 (8)	0.0449 (9)	−0.0163 (7)	−0.0060 (7)	−0.0162 (7)
C1	0.0182 (9)	0.0212 (9)	0.0288 (9)	−0.0062 (7)	0.0028 (7)	−0.0103 (7)
C2	0.0171 (9)	0.0233 (9)	0.0291 (9)	−0.0067 (7)	0.0035 (7)	−0.0098 (7)
C3	0.0231 (9)	0.0256 (9)	0.0287 (9)	−0.0088 (7)	0.0026 (7)	−0.0122 (8)
C4	0.0240 (10)	0.0307 (10)	0.0258 (9)	−0.0109 (8)	0.0015 (7)	−0.0111 (8)
C5	0.0211 (9)	0.0237 (9)	0.0331 (10)	−0.0070 (7)	0.0004 (8)	−0.0079 (8)
C6	0.0184 (9)	0.0244 (9)	0.0332 (10)	−0.0067 (7)	0.0031 (7)	−0.0118 (8)
C7	0.0194 (9)	0.0250 (9)	0.0273 (9)	−0.0083 (7)	0.0038 (7)	−0.0118 (7)
C8	0.0173 (9)	0.0212 (9)	0.0308 (9)	−0.0064 (7)	0.0045 (7)	−0.0101 (7)
C9	0.0299 (11)	0.0227 (9)	0.0382 (11)	−0.0026 (8)	0.0025 (8)	−0.0129 (8)
C10	0.0212 (9)	0.0274 (9)	0.0260 (9)	−0.0123 (7)	0.0048 (7)	−0.0107 (7)
C11	0.0239 (10)	0.0287 (10)	0.0299 (10)	−0.0085 (8)	0.0045 (8)	−0.0122 (8)
C12	0.0222 (10)	0.0313 (10)	0.0327 (10)	−0.0086 (8)	0.0020 (8)	−0.0076 (8)
C13	0.0260 (10)	0.0408 (12)	0.0272 (10)	−0.0178 (9)	0.0049 (8)	−0.0102 (8)
C14	0.0320 (11)	0.0383 (11)	0.0311 (10)	−0.0180 (9)	0.0102 (8)	−0.0176 (9)
C15	0.0279 (10)	0.0259 (9)	0.0310 (10)	−0.0118 (8)	0.0069 (8)	−0.0118 (8)
C16	0.0367 (12)	0.0562 (15)	0.0283 (10)	−0.0197 (11)	0.0034 (9)	−0.0112 (10)
C17	0.0298 (11)	0.0311 (10)	0.0316 (10)	−0.0036 (8)	0.0054 (8)	−0.0156 (8)
C18	0.0290 (11)	0.0328 (11)	0.0440 (12)	−0.0119 (9)	0.0085 (9)	−0.0189 (9)

Geometric parameters (Å, º) top

Br1—C4	1.8996 (19)	C9—H9C	0.9800
Br1—O2ⁱ	3.1284 (15)	C10—C11	1.396 (3)
S1—O2	1.4943 (15)	C10—C15	1.401 (3)
S1—C1	1.7658 (19)	C11—C12	1.384 (3)
S1—C17	1.810 (2)	C11—H11	0.9500
O1—C7	1.369 (2)	C12—C13	1.392 (3)
O1—C8	1.378 (2)	C12—H12	0.9500
C1—C8	1.370 (3)	C13—C14	1.395 (3)
C1—C2	1.447 (3)	C13—C16	1.503 (3)
C2—C7	1.389 (3)	C14—C15	1.377 (3)
C2—C3	1.396 (3)	C14—H14	0.9500
C3—C4	1.379 (3)	C15—H15	0.9500
C3—H3	0.9500	C16—H16A	0.9800
C4—C5	1.397 (3)	C16—H16B	0.9800
C5—C6	1.382 (3)	C16—H16C	0.9800
C5—H5	0.9500	C17—C18	1.519 (3)
C6—C7	1.390 (3)	C17—H17A	0.9900
C6—C9	1.496 (3)	C17—H17B	0.9900
C8—C10	1.456 (3)	C18—H18A	0.9800
C9—H9A	0.9800	C18—H18B	0.9800
C9—H9B	0.9800	C18—H18C	0.9800

C4—Br1—O2ⁱ	164.97 (7)	C11—C10—C8	122.23 (17)
O2—S1—C1	106.64 (9)	C15—C10—C8	119.43 (17)
O2—S1—C17	106.82 (10)	C12—C11—C10	120.49 (18)
C1—S1—C17	98.32 (10)	C12—C11—H11	119.8
C7—O1—C8	107.13 (14)	C10—C11—H11	119.8
C8—C1—C2	107.24 (16)	C11—C12—C13	121.33 (19)
C8—C1—S1	127.11 (15)	C11—C12—H12	119.3
C2—C1—S1	124.84 (14)	C13—C12—H12	119.3
C7—C2—C3	119.30 (17)	C12—C13—C14	117.90 (18)
C7—C2—C1	104.87 (16)	C12—C13—C16	121.8 (2)
C3—C2—C1	135.80 (17)	C14—C13—C16	120.3 (2)
C4—C3—C2	116.46 (17)	C15—C14—C13	121.33 (19)
C4—C3—H3	121.8	C15—C14—H14	119.3
C2—C3—H3	121.8	C13—C14—H14	119.3
C3—C4—C5	123.18 (18)	C14—C15—C10	120.62 (18)
C3—C4—Br1	119.36 (15)	C14—C15—H15	119.7
C5—C4—Br1	117.42 (14)	C10—C15—H15	119.7
C6—C5—C4	121.36 (17)	C13—C16—H16A	109.5
C6—C5—H5	119.3	C13—C16—H16B	109.5
C4—C5—H5	119.3	H16A—C16—H16B	109.5
C5—C6—C7	114.64 (17)	C13—C16—H16C	109.5
C5—C6—C9	123.41 (17)	H16A—C16—H16C	109.5
C7—C6—C9	121.92 (18)	H16B—C16—H16C	109.5
O1—C7—C2	110.82 (16)	C18—C17—S1	111.08 (15)
O1—C7—C6	124.11 (16)	C18—C17—H17A	109.4
C2—C7—C6	125.04 (18)	S1—C17—H17A	109.4
C1—C8—O1	109.93 (16)	C18—C17—H17B	109.4
C1—C8—C10	135.84 (17)	S1—C17—H17B	109.4
O1—C8—C10	114.21 (16)	H17A—C17—H17B	108.0
C6—C9—H9A	109.5	C17—C18—H18A	109.5
C6—C9—H9B	109.5	C17—C18—H18B	109.5
H9A—C9—H9B	109.5	H18A—C18—H18B	109.5
C6—C9—H9C	109.5	C17—C18—H18C	109.5
H9A—C9—H9C	109.5	H18A—C18—H18C	109.5
H9B—C9—H9C	109.5	H18B—C18—H18C	109.5
C11—C10—C15	118.32 (17)

O2—S1—C1—C8	−130.72 (18)	C5—C6—C7—C2	1.6 (3)
C17—S1—C1—C8	118.85 (18)	C9—C6—C7—C2	−176.86 (19)
O2—S1—C1—C2	37.58 (19)	C2—C1—C8—O1	−0.3 (2)
C17—S1—C1—C2	−72.85 (18)	S1—C1—C8—O1	169.66 (13)
C8—C1—C2—C7	0.9 (2)	C2—C1—C8—C10	177.6 (2)
S1—C1—C2—C7	−169.35 (14)	S1—C1—C8—C10	−12.4 (3)
C8—C1—C2—C3	179.1 (2)	C7—O1—C8—C1	−0.4 (2)
S1—C1—C2—C3	8.8 (3)	C7—O1—C8—C10	−178.87 (16)
C7—C2—C3—C4	1.0 (3)	C1—C8—C10—C11	−15.2 (4)
C1—C2—C3—C4	−177.0 (2)	O1—C8—C10—C11	162.70 (17)
C2—C3—C4—C5	0.1 (3)	C1—C8—C10—C15	166.5 (2)
C2—C3—C4—Br1	177.69 (14)	O1—C8—C10—C15	−15.6 (3)
C3—C4—C5—C6	−0.4 (3)	C15—C10—C11—C12	−0.1 (3)
Br1—C4—C5—C6	−178.01 (15)	C8—C10—C11—C12	−178.39 (19)
C4—C5—C6—C7	−0.4 (3)	C10—C11—C12—C13	0.8 (3)
C4—C5—C6—C9	177.98 (19)	C11—C12—C13—C14	−0.7 (3)
C8—O1—C7—C2	1.0 (2)	C11—C12—C13—C16	179.0 (2)
C8—O1—C7—C6	−176.82 (18)	C12—C13—C14—C15	−0.2 (3)
C3—C2—C7—O1	−179.73 (16)	C16—C13—C14—C15	−179.9 (2)
C1—C2—C7—O1	−1.2 (2)	C13—C14—C15—C10	0.9 (3)
C3—C2—C7—C6	−1.9 (3)	C11—C10—C15—C14	−0.8 (3)
C1—C2—C7—C6	176.64 (18)	C8—C10—C15—C14	177.56 (18)
C5—C6—C7—O1	179.12 (17)	O2—S1—C17—C18	171.58 (14)
C9—C6—C7—O1	0.7 (3)	C1—S1—C17—C18	−78.14 (16)

Symmetry code: (i) −x+2, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇BrO₂S
M_r	377.29
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.3921 (2), 10.2909 (3), 11.8701 (3)
α, β, γ (°)	68.867 (1), 89.146 (1), 71.361 (1)
V (Å³)	792.91 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.73
Crystal size (mm)	0.37 × 0.25 × 0.22

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.535, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	13645, 3457, 3145
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.076, 1.04
No. of reflections	3457
No. of parameters	202
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.47

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

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
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Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o2960. 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
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Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305–311. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar