Literature DB >> 21588356

5-Bromo-3-(4-fluoro-phenyl-sulfon-yl)-2-methyl-1-benzofuran.

Hong Dae Choi, Pil Ja Seo, Byeng Wha Son, Uk Lee.

Abstract

In the title compound, C(15)H(10)BrFO(3)S, the 4-fluoro-phenyl ring makes a dihedral angle of 76.51 (6)° with the plane of the benzofuran fragment. In the crystal, mol-ecules are linked by weak non-classical inter-molecular C-H⋯O hydrogen bonds and an aromatic π-π inter-action between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.540 (3) Å].

Entities: Chemical Disease Gene

Year: 2010 PMID： 21588356 PMCID： PMC3007450 DOI： 10.1107/S1600536810027741

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the pharmacological 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 ▶). For the structures of related 3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010 ▶).

Experimental

Crystal data

C15H10BrFO3S M = 369.20 Triclinic, a = 7.4519 (3) Å b = 9.2313 (4) Å c = 11.4570 (5) Å α = 70.652 (2)° β = 78.495 (2)° γ = 68.371 (2)° V = 688.57 (5) Å3 Z = 2 Mo Kα radiation μ = 3.15 mm−1 T = 174 K 0.35 × 0.33 × 0.31 mm

Data collection

Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.405, T max = 0.439 11771 measured reflections 3137 independent reflections 2741 reflections with I > 2σ(I) R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.030 wR(F 2) = 0.082 S = 1.08 3137 reflections 191 parameters H-atom parameters constrained Δρmax = 0.23 e Å−3 Δρmin = −0.58 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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810027741/rk2220sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027741/rk2220Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₅H₁₀BrFO₃S	Z = 2
M_r = 369.20	F(000) = 368
Triclinic, P1	D_x = 1.781 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4519 (3) Å	Cell parameters from 7545 reflections
b = 9.2313 (4) Å	θ = 2.5–27.5°
c = 11.4570 (5) Å	µ = 3.15 mm⁻¹
α = 70.652 (2)°	T = 174 K
β = 78.495 (2)°	Block, colourless
γ = 68.371 (2)°	0.35 × 0.33 × 0.31 mm
V = 688.57 (5) Å³

Bruker SMART APEXII CCD diffractometer	3137 independent reflections
Radiation source: rotating anode	2741 reflections with I > 2σ(I)
graphite multilayer	R_int = 0.040
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 1.9°
φ– and ω–scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
T_min = 0.405, T_max = 0.439	l = −14→14
11771 measured reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0442P)² + 0.0824P] where P = (F_o² + 2F_c²)/3
3137 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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.

	x	y	z	U_iso*/U_eq
Br	0.75115 (3)	0.08439 (3)	0.82425 (2)	0.04195 (10)
S	0.46680 (7)	0.39556 (6)	0.29542 (5)	0.02422 (12)
F	1.0254 (2)	0.73795 (18)	0.06607 (16)	0.0525 (4)
O1	0.7799 (2)	−0.06606 (16)	0.35232 (13)	0.0283 (3)
O2	0.3581 (2)	0.41371 (18)	0.19806 (14)	0.0315 (3)
O3	0.3671 (2)	0.44837 (18)	0.40280 (14)	0.0331 (3)
C1	0.6054 (3)	0.1915 (2)	0.34920 (18)	0.0244 (4)
C2	0.6740 (3)	0.1097 (2)	0.47105 (18)	0.0229 (4)
C3	0.6615 (3)	0.1518 (2)	0.57888 (18)	0.0258 (4)
H3	0.5897	0.2583	0.5852	0.031*
C4	0.7587 (3)	0.0310 (3)	0.67691 (19)	0.0273 (4)
C5	0.8637 (3)	−0.1268 (3)	0.6709 (2)	0.0304 (5)
H5	0.9269	−0.2057	0.7407	0.037*
C6	0.8759 (3)	−0.1687 (2)	0.5639 (2)	0.0293 (5)
H6	0.9468	−0.2754	0.5577	0.035*
C7	0.7807 (3)	−0.0488 (2)	0.46705 (19)	0.0249 (4)
C8	0.6742 (3)	0.0817 (2)	0.28167 (19)	0.0262 (4)
C9	0.6637 (3)	0.0903 (3)	0.1523 (2)	0.0356 (5)
H9A	0.5777	0.1978	0.1109	0.053*
H9B	0.6128	0.0067	0.1516	0.053*
H9C	0.7936	0.0722	0.1083	0.053*
C10	0.6374 (3)	0.4971 (2)	0.22804 (19)	0.0240 (4)
C11	0.6702 (3)	0.5460 (3)	0.0994 (2)	0.0305 (5)
H11	0.6034	0.5226	0.0491	0.037*
C12	0.8000 (3)	0.6283 (3)	0.0455 (2)	0.0373 (5)
H12	0.8227	0.6642	−0.0423	0.045*
C13	0.8962 (3)	0.6577 (3)	0.1208 (2)	0.0354 (5)
C14	0.8684 (3)	0.6105 (3)	0.2478 (2)	0.0343 (5)
H14	0.9387	0.6324	0.2969	0.041*
C15	0.7348 (3)	0.5297 (2)	0.3030 (2)	0.0283 (4)
H15	0.7103	0.4971	0.3908	0.034*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.04901 (16)	0.04935 (17)	0.02543 (14)	−0.00911 (12)	−0.01044 (10)	−0.01172 (11)
S	0.0240 (2)	0.0251 (3)	0.0201 (2)	−0.00436 (19)	−0.00352 (19)	−0.0053 (2)
F	0.0530 (9)	0.0482 (9)	0.0613 (10)	−0.0315 (7)	−0.0082 (7)	−0.0033 (8)
O1	0.0304 (7)	0.0261 (7)	0.0282 (8)	−0.0070 (6)	−0.0013 (6)	−0.0107 (6)
O2	0.0301 (7)	0.0349 (8)	0.0286 (8)	−0.0102 (6)	−0.0104 (6)	−0.0038 (7)
O3	0.0335 (8)	0.0316 (8)	0.0249 (8)	−0.0015 (6)	0.0021 (6)	−0.0091 (7)
C1	0.0239 (9)	0.0257 (10)	0.0216 (10)	−0.0067 (8)	−0.0014 (8)	−0.0060 (8)
C2	0.0202 (8)	0.0238 (10)	0.0231 (10)	−0.0077 (7)	−0.0004 (7)	−0.0050 (8)
C3	0.0264 (9)	0.0249 (10)	0.0232 (10)	−0.0062 (8)	−0.0019 (8)	−0.0058 (8)
C4	0.0239 (9)	0.0341 (11)	0.0226 (10)	−0.0098 (8)	−0.0026 (8)	−0.0060 (9)
C5	0.0269 (10)	0.0305 (11)	0.0276 (11)	−0.0086 (8)	−0.0053 (8)	0.0006 (9)
C6	0.0242 (9)	0.0231 (10)	0.0344 (12)	−0.0048 (8)	−0.0012 (9)	−0.0044 (9)
C7	0.0240 (9)	0.0260 (10)	0.0256 (10)	−0.0102 (8)	0.0003 (8)	−0.0076 (8)
C8	0.0254 (9)	0.0277 (10)	0.0241 (10)	−0.0078 (8)	−0.0022 (8)	−0.0064 (8)
C9	0.0418 (12)	0.0394 (13)	0.0278 (12)	−0.0100 (10)	−0.0040 (10)	−0.0154 (10)
C10	0.0256 (9)	0.0202 (9)	0.0245 (10)	−0.0037 (7)	−0.0048 (8)	−0.0069 (8)
C11	0.0368 (11)	0.0335 (11)	0.0242 (10)	−0.0135 (9)	−0.0076 (9)	−0.0070 (9)
C12	0.0432 (13)	0.0379 (13)	0.0295 (12)	−0.0179 (10)	−0.0021 (10)	−0.0036 (10)
C13	0.0363 (11)	0.0255 (11)	0.0456 (14)	−0.0126 (9)	−0.0061 (10)	−0.0072 (10)
C14	0.0358 (11)	0.0271 (11)	0.0459 (14)	−0.0074 (9)	−0.0137 (10)	−0.0153 (10)
C15	0.0323 (10)	0.0248 (10)	0.0253 (10)	−0.0005 (8)	−0.0084 (8)	−0.0105 (9)

Br—C4	1.894 (2)	C6—C7	1.371 (3)
S—O2	1.4369 (15)	C6—H6	0.9500
S—O3	1.4385 (14)	C8—C9	1.474 (3)
S—C1	1.745 (2)	C9—H9A	0.9800
S—C10	1.760 (2)	C9—H9B	0.9800
F—C13	1.359 (3)	C9—H9C	0.9800
O1—C8	1.366 (2)	C10—C11	1.390 (3)
O1—C7	1.377 (2)	C10—C15	1.391 (3)
C1—C8	1.367 (3)	C11—C12	1.374 (3)
C1—C2	1.443 (3)	C11—H11	0.9500
C2—C3	1.390 (3)	C12—C13	1.370 (3)
C2—C7	1.396 (3)	C12—H12	0.9500
C3—C4	1.389 (3)	C13—C14	1.370 (3)
C3—H3	0.9500	C14—C15	1.390 (3)
C4—C5	1.394 (3)	C14—H14	0.9500
C5—C6	1.380 (3)	C15—H15	0.9500
C5—H5	0.9500

O2—S—O3	119.74 (9)	O1—C8—C1	110.28 (18)
O2—S—C1	108.91 (9)	O1—C8—C9	115.36 (17)
O3—S—C1	106.96 (9)	C1—C8—C9	134.3 (2)
O2—S—C10	107.49 (9)	C8—C9—H9A	109.5
O3—S—C10	107.99 (10)	C8—C9—H9B	109.5
C1—S—C10	104.78 (9)	H9A—C9—H9B	109.5
C8—O1—C7	107.04 (14)	C8—C9—H9C	109.5
C8—C1—C2	107.63 (17)	H9A—C9—H9C	109.5
C8—C1—S	125.95 (17)	H9B—C9—H9C	109.5
C2—C1—S	126.38 (15)	C11—C10—C15	120.92 (19)
C3—C2—C7	119.08 (18)	C11—C10—S	118.93 (16)
C3—C2—C1	136.46 (18)	C15—C10—S	120.14 (16)
C7—C2—C1	104.44 (17)	C12—C11—C10	119.6 (2)
C4—C3—C2	116.97 (18)	C12—C11—H11	120.2
C4—C3—H3	121.5	C10—C11—H11	120.2
C2—C3—H3	121.5	C13—C12—C11	118.7 (2)
C3—C4—C5	122.9 (2)	C13—C12—H12	120.7
C3—C4—Br	118.43 (15)	C11—C12—H12	120.7
C5—C4—Br	118.66 (16)	F—C13—C14	118.7 (2)
C6—C5—C4	120.1 (2)	F—C13—C12	118.0 (2)
C6—C5—H5	119.9	C14—C13—C12	123.4 (2)
C4—C5—H5	119.9	C13—C14—C15	118.3 (2)
C7—C6—C5	116.77 (18)	C13—C14—H14	120.9
C7—C6—H6	121.6	C15—C14—H14	120.9
C5—C6—H6	121.6	C14—C15—C10	119.2 (2)
C6—C7—O1	125.27 (18)	C14—C15—H15	120.4
C6—C7—C2	124.12 (19)	C10—C15—H15	120.4
O1—C7—C2	110.59 (17)

O2—S—C1—C8	28.0 (2)	C1—C2—C7—O1	0.0 (2)
O3—S—C1—C8	158.69 (18)	C7—O1—C8—C1	−1.0 (2)
C10—S—C1—C8	−86.8 (2)	C7—O1—C8—C9	177.27 (18)
O2—S—C1—C2	−154.43 (17)	C2—C1—C8—O1	0.9 (2)
O3—S—C1—C2	−23.7 (2)	S—C1—C8—O1	178.94 (14)
C10—S—C1—C2	90.80 (19)	C2—C1—C8—C9	−176.8 (2)
C8—C1—C2—C3	177.7 (2)	S—C1—C8—C9	1.2 (4)
S—C1—C2—C3	−0.3 (3)	O2—S—C10—C11	−12.64 (18)
C8—C1—C2—C7	−0.6 (2)	O3—S—C10—C11	−143.12 (15)
S—C1—C2—C7	−178.53 (15)	C1—S—C10—C11	103.12 (17)
C7—C2—C3—C4	0.3 (3)	O2—S—C10—C15	166.35 (15)
C1—C2—C3—C4	−177.8 (2)	O3—S—C10—C15	35.87 (18)
C2—C3—C4—C5	−0.6 (3)	C1—S—C10—C15	−77.89 (17)
C2—C3—C4—Br	178.41 (14)	C15—C10—C11—C12	−0.3 (3)
C3—C4—C5—C6	0.6 (3)	S—C10—C11—C12	178.67 (17)
Br—C4—C5—C6	−178.47 (15)	C10—C11—C12—C13	1.0 (3)
C4—C5—C6—C7	−0.1 (3)	C11—C12—C13—F	179.4 (2)
C5—C6—C7—O1	178.37 (18)	C11—C12—C13—C14	−0.6 (4)
C5—C6—C7—C2	−0.2 (3)	F—C13—C14—C15	179.46 (19)
C8—O1—C7—C6	−178.15 (19)	C12—C13—C14—C15	−0.5 (3)
C8—O1—C7—C2	0.6 (2)	C13—C14—C15—C10	1.2 (3)
C3—C2—C7—C6	0.1 (3)	C11—C10—C15—C14	−0.8 (3)
C1—C2—C7—C6	178.73 (19)	S—C10—C15—C14	−179.79 (15)
C3—C2—C7—O1	−178.63 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O3ⁱ	0.95	2.49	3.362 (3)	152
C11—H11···O2ⁱⁱ	0.95	2.67	3.345 (3)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O3ⁱ	0.95	2.49	3.362 (3)	152
C11—H11⋯O2ⁱⁱ	0.95	2.67	3.345 (3)	128

Symmetry codes: (i) ; (ii) .

8 in total

1. Benzofurans and another constituent from seeds of Styrax officinalis.

Authors: Yurdanur Yayla Akgul; Huseyin Anil
Journal: Phytochemistry Date: 2003-08 Impact factor: 4.072

2. A new structural alternative in benzo[b]furans for antimicrobial activity.

Authors: M Wahab Khan; M Jahangir Alam; M A Rashid; R Chowdhury
Journal: Bioorg Med Chem Date: 2005-08-15 Impact factor: 3.641

3. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

4. Artoindonesianins X and Y, two isoprenylated 2-arylbenzofurans, from Artocarpus fretessi (Moraceae).

Authors: Nunuk H Soekamto; Sjamsul A Achmad; Emilio L Ghisalberti; Euis H Hakim; Yana M Syah
Journal: Phytochemistry Date: 2003-10 Impact factor: 4.072

5. 3-(4-Fluoro-phenyl-sulfon-yl)-5-isopropyl-2-methyl-1-benzofuran.

Authors: Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-04-14

6. Synthesis of potent antitumor and antiviral benzofuran derivatives.

Authors: Shadia A Galal; Amira S Abd El-All; Mohamed M Abdallah; Hoda I El-Diwani
Journal: Bioorg Med Chem Lett Date: 2009-03-21 Impact factor: 2.823

7. 5-Fluoro-3-(4-fluoro-phenyl-sulfon-yl)-2-methyl-1-benzofuran.

Authors: Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-07-03

8. 3-(4-Fluoro-phenyl-sulfon-yl)-2,5,7-trimethyl-1-benzofuran.

Authors: Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-06-26