Crystal structure of 3-(2-bromo­phenyl­sulfon­yl)-2,5,7-trimethyl-1-benzo­furan

Choi, H.D.; Lee, U.

doi:10.1107/S1600536814021850

organic compounds

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ISSN: 2056-9890

Volume 70| Part 11| November 2014| Page o1152

doi:10.1107/S1600536814021850

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Crystal structure of 3-(2-bromophenylsulfonyl)-2,5,7-trimethyl-1-benzofuran

Hong Dae Choi ^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

Edited by J. T. Mague, Tulane University, USA (Received 29 September 2014; accepted 3 October 2014; online 8 October 2014)

In the title compound, C₁₇H₁₅BrO₃S, the dihedral angle between the planes of the benzofuran ring system [r.m.s. deviation = 0.016 (2) Å] and the 2-bromophenyl ring is 82.93 (6)°. In the crystal, molecules are linked via pairs of C—H⋯π hydrogen bonds and π–π interactions between the benzene and furan rings of neighbouring molecules [centroid–centroid distance = 3.881 (2) Å] into inversion-related dimers along the b-axis direction. These dimers are further linked by short Br⋯O [3.185 (2) Å] contacts.

Keywords: crystal structure; benzofuran; 2-bromophenyl; C—H⋯π hydrogen bonds; π–π interactions; Br⋯O contact.

CCDC reference: 1027593

1. Related literature

For a related structure and background to benzofuran derivatives, see: Choi & Lee (2014 ). For further synthetic details, see: Choi et al. (1999 ). For a review of halogen bonding, see: Politzer et al. (2007 ).

2. Experimental

2.1. Crystal data

C₁₇H₁₅BrO₃S
M_r = 379.26
Monoclinic, P 2₁ /n
a = 7.8969 (2) Å
b = 8.1489 (2) Å
c = 24.3146 (6) Å
β = 96.210 (1)°
V = 1555.49 (7) Å³
Z = 4
Mo Kα radiation
μ = 2.79 mm⁻¹
T = 173 K
0.31 × 0.27 × 0.13 mm

2.2. Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.479, T_max = 0.713
27395 measured reflections
3867 independent reflections
3130 reflections with I > 2σ(I)
R_int = 0.042

2.3. Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.080
S = 1.03
3867 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.34 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
C9—H9C⋯Cg1ⁱ	0.98	2.84	3.608 (2)	136
Symmetry code: (i) -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 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1027593

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814021850/mw2127sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814021850/mw2127Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814021850/mw2127Isup3.cml

checkCIF report

Comment top

As a part of our continuing program for benzofuran derivatives (Choi & Lee, 2014), 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 0.016 (2) Å from the least-squares plane defined by the nine constituent atoms. The 2-bromophenyl ring is essentially planar, with a mean deviation of 0.004 (2) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring and the 2-bromophenyl ring is 82.93 (6)°. In the crystal structure (Fig. 2), molecules are linked via two different pairs of C—H···π hydrogen bonds (Table 1, Cg1 is the centroid of the C2–C7 benzene ring) and π–π interactions between the benzene and furan rings of neighbouring molecules, with a Cg1···Cg2ⁱⁱⁱ distance of 3.881 (2) Å and an interplanar distance of 3.562 (2) Å resulting in a slippage of 1.541 (2) Å (Cg2 is the centroid of the C1/C2/C7/O1/C8 furan ring), into inversion-related dimers along the b-axis direction. These dimers are further linked by halogen-bondings (Politzer et al. 2007) between the bromine and the O atom of the O═S═O unit [Br1..O3ⁱⁱ = 3.185 (2) Å, C17—Br1···O3ⁱⁱ = 164.49 (7)°, symmetry code: (ii) - x + 1/2, y - 1/2, - z + 3/2].

Related literature top

For a related structure and background to benzofuran derivatives, see: Choi & Lee (2014). For further synthetic details, see: Choi et al. (1999). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental top

The starting material 3-(2-bromophenylsulfanyl)-2,5,7-trimethyl-1-benzofuran was prepared by a literature method (Choi et al., 1999). 3-Chloroperoxybenzoic acid (77%, 403 mg, 1.8 mmol) was added in small portions to a stirred solution of 3-(2-bromophenylsulfanyl)-2,5,7-trimethyl-1-benzofuran (278 mg, 0.8 mmol) in dichloromethane (30 ml) at 273 K. After being stirred at room temperature for 8h, the mixture was washed with saturated sodium bicarbonate solution (2 X 10 ml) 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, 4:1 v/v) to afford the title compound as a colorless solid [yield 72% (218 mg); m.p. 453–454 K; R_f = 0.51 (hexane-ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound (21 mg) in acetone (15 ml) 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 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···π, π–π and Br···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 + 1, - y + 1, - z + 1; (ii) - x + 1/2, y - 1/2, - z + 3/2 ; (iii) - x, - y + 1, - z + 1; (iv) - x + 1/2, y + 1/2, - z + 3/2.]

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

Crystal data top

C₁₇H₁₅BrO₃S	F(000) = 768
M_r = 379.26	D_x = 1.619 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 454–453 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.8969 (2) Å	Cell parameters from 7387 reflections
b = 8.1489 (2) Å	θ = 2.6–26.1°
c = 24.3146 (6) Å	µ = 2.79 mm⁻¹
β = 96.210 (1)°	T = 173 K
V = 1555.49 (7) Å³	Block, colourless
Z = 4	0.31 × 0.27 × 0.13 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3867 independent reflections
Radiation source: rotating anode	3130 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.042
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 1.7°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
T_min = 0.479, T_max = 0.713	l = −31→32
27395 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)] = 0.031	Hydrogen site location: difference Fourier map
wR(F²) = 0.080	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0401P)² + 0.8758P] where P = (F_o² + 2F_c²)/3
3867 reflections	(Δ/σ)_max = 0.001
202 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₇H₁₅BrO₃S	V = 1555.49 (7) Å³
M_r = 379.26	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.8969 (2) Å	µ = 2.79 mm⁻¹
b = 8.1489 (2) Å	T = 173 K
c = 24.3146 (6) Å	0.31 × 0.27 × 0.13 mm
β = 96.210 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3867 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3130 reflections with I > 2σ(I)
T_min = 0.479, T_max = 0.713	R_int = 0.042
27395 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.03	Δρ_max = 0.51 e Å⁻³
3867 reflections	Δρ_min = −0.34 e Å⁻³
202 parameters

Special details top

Experimental. ¹H NMR (δ p.p.m., CDCl₃, 400 Hz): 8.49 (d, J = 6.12 Hz, 1H), 7.65 (d, J =6.84 Hz, 1H), 7.53-7.58 (m, 1H), 7.38-7.43 (m, 1H), 7.06 (s, 1H), 6.88 (s, 1H), 2.84 (s, 3H), 2.43 (s, 3H), 2.31 (s, 3H).

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	0.46256 (3)	0.42412 (3)	0.713662 (9)	0.03093 (9)
S1	0.12638 (7)	0.65915 (7)	0.65837 (2)	0.02299 (13)
O1	0.1202 (2)	0.22941 (18)	0.58642 (6)	0.0280 (4)
O2	0.0262 (2)	0.7852 (2)	0.62933 (7)	0.0320 (4)
O3	0.0830 (2)	0.6094 (2)	0.71169 (7)	0.0311 (4)
C1	0.1294 (3)	0.4896 (3)	0.61574 (9)	0.0222 (4)
C2	0.1822 (3)	0.4890 (3)	0.56071 (8)	0.0208 (4)
C3	0.2360 (3)	0.6058 (3)	0.52431 (9)	0.0241 (4)
H3	0.2402	0.7190	0.5337	0.029*
C4	0.2832 (3)	0.5521 (3)	0.47408 (9)	0.0257 (5)
C5	0.2767 (3)	0.3855 (3)	0.46099 (9)	0.0273 (5)
H5	0.3106	0.3521	0.4264	0.033*
C6	0.2235 (3)	0.2660 (3)	0.49579 (9)	0.0270 (5)
C7	0.1761 (3)	0.3251 (3)	0.54484 (9)	0.0229 (4)
C8	0.0946 (3)	0.3321 (3)	0.62932 (9)	0.0258 (5)
C9	0.3440 (3)	0.6725 (3)	0.43345 (10)	0.0350 (6)
H9A	0.2662	0.7664	0.4294	0.053*
H9B	0.3467	0.6188	0.3975	0.053*
H9C	0.4587	0.7105	0.4470	0.053*
C10	0.2218 (4)	0.0869 (3)	0.48191 (12)	0.0412 (6)
H10A	0.2464	0.0228	0.5159	0.062*
H10B	0.3084	0.0642	0.4570	0.062*
H10C	0.1093	0.0566	0.4638	0.062*
C11	0.0392 (3)	0.2511 (3)	0.67846 (10)	0.0378 (6)
H11A	0.1317	0.1821	0.6958	0.057*
H11B	−0.0608	0.1827	0.6674	0.057*
H11C	0.0099	0.3344	0.7049	0.057*
C12	0.3401 (3)	0.7318 (3)	0.66497 (8)	0.0220 (4)
C13	0.3630 (3)	0.8918 (3)	0.64809 (10)	0.0286 (5)
H13	0.2678	0.9543	0.6327	0.034*
C14	0.5241 (3)	0.9611 (3)	0.65352 (11)	0.0365 (6)
H14	0.5390	1.0714	0.6423	0.044*
C15	0.6626 (3)	0.8704 (3)	0.67508 (11)	0.0363 (6)
H15	0.7730	0.9181	0.6785	0.044*
C16	0.6417 (3)	0.7101 (3)	0.69174 (10)	0.0315 (5)
H16	0.7377	0.6476	0.7063	0.038*
C17	0.4809 (3)	0.6409 (3)	0.68725 (9)	0.0238 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03549 (14)	0.02720 (13)	0.02903 (14)	0.00525 (10)	−0.00148 (9)	0.00300 (9)
S1	0.0223 (3)	0.0245 (3)	0.0227 (3)	0.0008 (2)	0.0050 (2)	−0.0029 (2)
O1	0.0390 (9)	0.0201 (7)	0.0247 (8)	−0.0047 (7)	0.0030 (7)	0.0020 (6)
O2	0.0277 (8)	0.0306 (9)	0.0366 (9)	0.0082 (7)	−0.0009 (7)	−0.0044 (7)
O3	0.0319 (8)	0.0388 (10)	0.0243 (8)	−0.0031 (7)	0.0113 (7)	−0.0042 (7)
C1	0.0231 (10)	0.0228 (10)	0.0209 (11)	−0.0007 (8)	0.0030 (8)	−0.0005 (8)
C2	0.0197 (10)	0.0225 (10)	0.0201 (10)	0.0011 (8)	0.0018 (8)	0.0005 (8)
C3	0.0275 (11)	0.0204 (10)	0.0244 (11)	−0.0008 (8)	0.0033 (9)	−0.0006 (8)
C4	0.0248 (11)	0.0295 (11)	0.0229 (11)	0.0006 (9)	0.0031 (9)	0.0018 (9)
C5	0.0304 (11)	0.0307 (12)	0.0214 (11)	0.0033 (9)	0.0052 (9)	−0.0048 (9)
C6	0.0299 (11)	0.0255 (11)	0.0248 (12)	0.0019 (9)	−0.0001 (9)	−0.0043 (9)
C7	0.0258 (11)	0.0208 (10)	0.0217 (11)	−0.0016 (8)	0.0012 (8)	0.0016 (8)
C8	0.0282 (11)	0.0258 (11)	0.0236 (11)	−0.0030 (9)	0.0031 (9)	−0.0012 (9)
C9	0.0391 (14)	0.0392 (14)	0.0283 (13)	−0.0014 (11)	0.0106 (11)	0.0039 (11)
C10	0.0618 (18)	0.0252 (12)	0.0368 (15)	0.0020 (12)	0.0065 (13)	−0.0082 (11)
C11	0.0508 (16)	0.0351 (13)	0.0288 (13)	−0.0102 (12)	0.0098 (11)	0.0050 (11)
C12	0.0242 (10)	0.0244 (11)	0.0180 (10)	−0.0011 (8)	0.0055 (8)	−0.0046 (8)
C13	0.0346 (12)	0.0241 (11)	0.0278 (12)	0.0005 (9)	0.0057 (10)	−0.0006 (9)
C14	0.0477 (15)	0.0286 (12)	0.0349 (14)	−0.0092 (11)	0.0124 (12)	−0.0037 (10)
C15	0.0308 (12)	0.0455 (15)	0.0339 (14)	−0.0116 (11)	0.0085 (11)	−0.0094 (12)
C16	0.0256 (11)	0.0428 (14)	0.0261 (12)	0.0003 (10)	0.0034 (9)	−0.0053 (10)
C17	0.0293 (11)	0.0262 (11)	0.0163 (10)	0.0023 (9)	0.0044 (8)	−0.0027 (8)

Geometric parameters (Å, º) top

Br1—C17	1.890 (2)	C8—C11	1.472 (3)
Br1—O3ⁱ	22.6093 (17)	C9—H9A	0.9800
S1—O3	1.4345 (16)	C9—H9B	0.9800
S1—O2	1.4348 (17)	C9—H9C	0.9800
S1—C1	1.729 (2)	C10—H10A	0.9800
S1—C12	1.779 (2)	C10—H10B	0.9800
O1—C8	1.369 (3)	C10—H10C	0.9800
O1—C7	1.386 (3)	C11—H11A	0.9800
C1—C8	1.361 (3)	C11—H11B	0.9800
C1—C2	1.444 (3)	C11—H11C	0.9800
C2—C7	1.390 (3)	C12—C13	1.385 (3)
C2—C3	1.397 (3)	C12—C17	1.396 (3)
C3—C4	1.386 (3)	C13—C14	1.385 (4)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.395 (3)	C14—C15	1.376 (4)
C4—C9	1.507 (3)	C14—H14	0.9500
C5—C6	1.385 (3)	C15—C16	1.383 (4)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.375 (3)	C16—C17	1.383 (3)
C6—C10	1.497 (3)	C16—H16	0.9500

C17—Br1—O3ⁱ	76.20 (6)	H9A—C9—H9B	109.5
O3—S1—O2	118.32 (10)	C4—C9—H9C	109.5
O3—S1—C1	109.64 (10)	H9A—C9—H9C	109.5
O2—S1—C1	108.65 (10)	H9B—C9—H9C	109.5
O3—S1—C12	109.22 (10)	C6—C10—H10A	109.5
O2—S1—C12	105.85 (10)	C6—C10—H10B	109.5
C1—S1—C12	104.19 (10)	H10A—C10—H10B	109.5
C8—O1—C7	107.27 (16)	C6—C10—H10C	109.5
C8—C1—C2	107.93 (19)	H10A—C10—H10C	109.5
C8—C1—S1	126.30 (17)	H10B—C10—H10C	109.5
C2—C1—S1	125.62 (16)	C8—C11—H11A	109.5
C7—C2—C3	118.87 (19)	C8—C11—H11B	109.5
C7—C2—C1	104.80 (18)	H11A—C11—H11B	109.5
C3—C2—C1	136.3 (2)	C8—C11—H11C	109.5
C4—C3—C2	118.2 (2)	H11A—C11—H11C	109.5
C4—C3—H3	120.9	H11B—C11—H11C	109.5
C2—C3—H3	120.9	C13—C12—C17	119.4 (2)
C3—C4—C5	120.1 (2)	C13—C12—S1	116.07 (17)
C3—C4—C9	120.5 (2)	C17—C12—S1	124.50 (17)
C5—C4—C9	119.4 (2)	C12—C13—C14	120.3 (2)
C6—C5—C4	123.5 (2)	C12—C13—H13	119.9
C6—C5—H5	118.3	C14—C13—H13	119.9
C4—C5—H5	118.3	C15—C14—C13	120.1 (2)
C7—C6—C5	114.4 (2)	C15—C14—H14	120.0
C7—C6—C10	122.7 (2)	C13—C14—H14	120.0
C5—C6—C10	122.9 (2)	C14—C15—C16	120.3 (2)
C6—C7—O1	125.00 (19)	C14—C15—H15	119.9
C6—C7—C2	124.9 (2)	C16—C15—H15	119.9
O1—C7—C2	110.03 (18)	C17—C16—C15	120.0 (2)
C1—C8—O1	109.95 (18)	C17—C16—H16	120.0
C1—C8—C11	134.9 (2)	C15—C16—H16	120.0
O1—C8—C11	115.2 (2)	C16—C17—C12	120.0 (2)
C4—C9—H9A	109.5	C16—C17—Br1	117.25 (18)
C4—C9—H9B	109.5	C12—C17—Br1	122.73 (17)

O3—S1—C1—C8	0.8 (2)	C1—C2—C7—O1	1.1 (2)
O2—S1—C1—C8	−129.9 (2)	C2—C1—C8—O1	−0.4 (2)
C12—S1—C1—C8	117.6 (2)	S1—C1—C8—O1	−176.16 (16)
O3—S1—C1—C2	−174.23 (18)	C2—C1—C8—C11	178.8 (3)
O2—S1—C1—C2	55.1 (2)	S1—C1—C8—C11	3.0 (4)
C12—S1—C1—C2	−57.4 (2)	C7—O1—C8—C1	1.1 (2)
C8—C1—C2—C7	−0.4 (2)	C7—O1—C8—C11	−178.3 (2)
S1—C1—C2—C7	175.34 (16)	O3—S1—C12—C13	−121.32 (17)
C8—C1—C2—C3	−178.9 (2)	O2—S1—C12—C13	7.10 (19)
S1—C1—C2—C3	−3.1 (4)	C1—S1—C12—C13	121.60 (18)
C7—C2—C3—C4	−0.8 (3)	O3—S1—C12—C17	56.5 (2)
C1—C2—C3—C4	177.4 (2)	O2—S1—C12—C17	−175.07 (17)
C2—C3—C4—C5	−0.1 (3)	C1—S1—C12—C17	−60.6 (2)
C2—C3—C4—C9	−179.4 (2)	C17—C12—C13—C14	−0.3 (3)
C3—C4—C5—C6	0.4 (4)	S1—C12—C13—C14	177.65 (18)
C9—C4—C5—C6	179.7 (2)	C12—C13—C14—C15	0.8 (4)
C4—C5—C6—C7	0.3 (3)	C13—C14—C15—C16	−0.4 (4)
C4—C5—C6—C10	−178.2 (2)	C14—C15—C16—C17	−0.6 (4)
C5—C6—C7—O1	−179.3 (2)	C15—C16—C17—C12	1.2 (3)
C10—C6—C7—O1	−0.8 (4)	C15—C16—C17—Br1	−177.56 (18)
C5—C6—C7—C2	−1.4 (3)	C13—C12—C17—C16	−0.7 (3)
C10—C6—C7—C2	177.2 (2)	S1—C12—C17—C16	−178.47 (17)
C8—O1—C7—C6	176.8 (2)	C13—C12—C17—Br1	177.95 (16)
C8—O1—C7—C2	−1.4 (2)	S1—C12—C17—Br1	0.2 (3)
C3—C2—C7—C6	1.7 (3)	O3ⁱ—Br1—C17—C16	−99.99 (17)
C1—C2—C7—C6	−177.1 (2)	O3ⁱ—Br1—C17—C12	81.32 (17)
C3—C2—C7—O1	179.89 (18)

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.

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
C9—H9C···Cg1ⁱⁱ	0.98	2.84	3.608 (2)	136

Symmetry code: (ii) −x+1, −y+1, −z+1.

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
C9—H9C···Cg1ⁱ	0.98	2.84	3.608 (2)	136.3

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The X-ray centre of Gyeongsang National University is acknowledged for providing access to the single-crystal diffractometer.

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. & Lee, U. (2014). Acta Cryst. E70, o1073–o1074. CSD CrossRef CAS IUCr Journals Google Scholar
Choi, H. D., Seo, P. J. & Son, B. W. (1999). J. Korean Chem. Soc. 43, 606–608. CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
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

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doi:10.1107/S1600536814021850

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 3-(2-bromo­phenyl­sulfon­yl)-2,5,7-tri­methyl-1-benzo­furan

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 3-(2-bromophenylsulfonyl)-2,5,7-trimethyl-1-benzofuran