Literature DB >> 21580704

5-Chloro-3-ethyl-sulfinyl-2-(4-fluoro-phen-yl)-7-methyl-1-benzofuran.

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

Abstract

In the title compound, C(17)H(14)ClFO(2)S, the 4-fluoro-phenyl ring is rotated slightly out of the benzofuran plane, as indicated by the dihedral angle of 8.32 (5)°. The crystal structure features a short Cl⋯O contact [3.092 (1) Å].

Entities: Chemical Disease Gene

Year: 2010 PMID： 21580704 PMCID： PMC2983861 DOI： 10.1107/S1600536810008627

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

Related literature

For the crystal structures of similar 3-ethylsulfinyl-2-(4-fluorophenyl)-5-halo-1-benzofuran derivatives, see: Choi et al. (2010 ▶). 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 a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C17H14ClFO2S M = 336.79 Triclinic, a = 7.3395 (1) Å b = 10.5618 (2) Å c = 11.2281 (2) Å α = 65.357 (1)° β = 85.232 (1)° γ = 69.939 (1)° V = 741.28 (2) Å3 Z = 2 Mo Kα radiation μ = 0.41 mm−1 T = 174 K 0.32 × 0.28 × 0.19 mm

Data collection

Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.879, T max = 0.926 13016 measured reflections 3440 independent reflections 3292 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.106 S = 1.06 3440 reflections 200 parameters H-atom parameters constrained Δρmax = 0.56 e Å−3 Δρmin = −0.59 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/S1600536810008627/vm2020sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008627/vm2020Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₇H₁₄ClFO₂S	Z = 2
M_r = 336.79	F(000) = 348
Triclinic, P1	D_x = 1.509 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3395 (1) Å	Cell parameters from 9795 reflections
b = 10.5618 (2) Å	θ = 2.3–27.6°
c = 11.2281 (2) Å	µ = 0.41 mm⁻¹
α = 65.357 (1)°	T = 174 K
β = 85.232 (1)°	Block, colourless
γ = 69.939 (1)°	0.32 × 0.28 × 0.19 mm
V = 741.28 (2) Å³

Bruker SMART APEXII CCD diffractometer	3440 independent reflections
Radiation source: Rotating Anode	3292 reflections with I > 2σ(I)
Bruker HELIOS graded multilayer optics	R_int = 0.023
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.6°, θ_min = 2.0°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
T_min = 0.879, T_max = 0.926	l = −14→14
13016 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)] = 0.038	Hydrogen site location: difference Fourier map
wR(F²) = 0.106	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0587P)² + 0.4567P] where P = (F_o² + 2F_c²)/3
3440 reflections	(Δ/σ)_max < 0.001
200 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

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.

	x	y	z	U_iso*/U_eq
Cl	−0.00786 (7)	0.72104 (5)	−0.07738 (4)	0.03543 (13)
S	0.36819 (5)	0.18932 (4)	0.42209 (3)	0.02170 (12)
F	0.58849 (19)	0.15390 (14)	1.03317 (10)	0.0457 (3)
O1	0.20083 (15)	0.56779 (11)	0.46554 (10)	0.0215 (2)
O2	0.21568 (18)	0.18590 (14)	0.34446 (12)	0.0329 (3)
C1	0.2932 (2)	0.37130 (16)	0.41330 (14)	0.0197 (3)
C2	0.1983 (2)	0.50252 (16)	0.29663 (14)	0.0202 (3)
C3	0.1543 (2)	0.53059 (17)	0.16738 (15)	0.0230 (3)
H3	0.1893	0.4537	0.1379	0.028*
C4	0.0568 (2)	0.67697 (18)	0.08464 (15)	0.0245 (3)
C5	0.0001 (2)	0.79229 (17)	0.12610 (15)	0.0242 (3)
H5	−0.0683	0.8904	0.0652	0.029*
C6	0.0420 (2)	0.76611 (16)	0.25427 (15)	0.0220 (3)
C7	0.1436 (2)	0.61881 (16)	0.33529 (14)	0.0200 (3)
C8	0.2915 (2)	0.41644 (16)	0.51177 (14)	0.0199 (3)
C9	0.3662 (2)	0.34377 (17)	0.64954 (14)	0.0213 (3)
C10	0.4879 (2)	0.19527 (18)	0.70685 (15)	0.0259 (3)
H10	0.5212	0.1385	0.6563	0.031*
C11	0.5603 (2)	0.13041 (19)	0.83696 (16)	0.0301 (3)
H11	0.6407	0.0292	0.8765	0.036*
C12	0.5129 (3)	0.2158 (2)	0.90716 (15)	0.0315 (4)
C13	0.3926 (3)	0.3615 (2)	0.85540 (16)	0.0318 (4)
H13	0.3610	0.4171	0.9071	0.038*
C14	0.3184 (2)	0.42539 (18)	0.72601 (16)	0.0266 (3)
H14	0.2341	0.5256	0.6888	0.032*
C15	−0.0198 (2)	0.88632 (18)	0.30237 (17)	0.0281 (3)
H15A	−0.1619	0.9314	0.2920	0.034*
H15B	0.0382	0.9620	0.2512	0.034*
H15C	0.0238	0.8442	0.3953	0.034*
C16	0.5748 (2)	0.19716 (18)	0.32281 (16)	0.0278 (3)
H16A	0.6081	0.1195	0.2891	0.033*
H16B	0.5414	0.2947	0.2466	0.033*
C17	0.7481 (2)	0.17387 (19)	0.40416 (17)	0.0296 (3)
H17A	0.7134	0.2489	0.4397	0.044*
H17B	0.8574	0.1827	0.3487	0.044*
H17C	0.7855	0.0750	0.4767	0.044*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0530 (3)	0.0313 (2)	0.0190 (2)	−0.01523 (19)	−0.00769 (17)	−0.00508 (16)
S	0.0252 (2)	0.01716 (18)	0.02138 (19)	−0.00641 (14)	−0.00133 (14)	−0.00688 (14)
F	0.0555 (7)	0.0562 (7)	0.0189 (5)	−0.0214 (6)	−0.0094 (5)	−0.0055 (5)
O1	0.0236 (5)	0.0192 (5)	0.0188 (5)	−0.0035 (4)	−0.0010 (4)	−0.0077 (4)
O2	0.0357 (6)	0.0309 (6)	0.0355 (7)	−0.0144 (5)	−0.0072 (5)	−0.0127 (5)
C1	0.0193 (6)	0.0173 (6)	0.0194 (6)	−0.0039 (5)	−0.0003 (5)	−0.0063 (5)
C2	0.0186 (6)	0.0187 (7)	0.0209 (7)	−0.0049 (5)	0.0005 (5)	−0.0070 (5)
C3	0.0264 (7)	0.0218 (7)	0.0205 (7)	−0.0076 (6)	−0.0003 (5)	−0.0085 (6)
C4	0.0278 (7)	0.0259 (8)	0.0185 (7)	−0.0104 (6)	−0.0024 (6)	−0.0063 (6)
C5	0.0234 (7)	0.0197 (7)	0.0241 (7)	−0.0062 (6)	−0.0029 (6)	−0.0040 (6)
C6	0.0192 (6)	0.0192 (7)	0.0245 (7)	−0.0044 (5)	0.0002 (5)	−0.0078 (6)
C7	0.0189 (6)	0.0204 (7)	0.0187 (6)	−0.0049 (5)	−0.0002 (5)	−0.0074 (5)
C8	0.0182 (6)	0.0183 (6)	0.0206 (7)	−0.0047 (5)	0.0011 (5)	−0.0067 (5)
C9	0.0206 (6)	0.0242 (7)	0.0186 (7)	−0.0098 (6)	0.0013 (5)	−0.0068 (6)
C10	0.0242 (7)	0.0267 (8)	0.0236 (7)	−0.0069 (6)	−0.0013 (6)	−0.0083 (6)
C11	0.0269 (8)	0.0306 (8)	0.0242 (8)	−0.0090 (6)	−0.0033 (6)	−0.0033 (6)
C12	0.0336 (8)	0.0425 (10)	0.0165 (7)	−0.0195 (7)	−0.0027 (6)	−0.0043 (7)
C13	0.0400 (9)	0.0387 (9)	0.0233 (8)	−0.0198 (8)	0.0040 (7)	−0.0143 (7)
C14	0.0315 (8)	0.0269 (8)	0.0218 (7)	−0.0120 (6)	0.0024 (6)	−0.0089 (6)
C15	0.0292 (8)	0.0204 (7)	0.0297 (8)	−0.0016 (6)	0.0003 (6)	−0.0109 (6)
C16	0.0284 (8)	0.0271 (8)	0.0257 (8)	−0.0038 (6)	0.0041 (6)	−0.0137 (6)
C17	0.0260 (7)	0.0267 (8)	0.0358 (9)	−0.0082 (6)	0.0036 (6)	−0.0136 (7)

Cl—O2ⁱ	3.092 (1)	C9—C14	1.401 (2)
Cl—C4	1.743 (2)	C9—C10	1.402 (2)
S—O2	1.493 (1)	C10—C11	1.389 (2)
S—C1	1.770 (2)	C10—H10	0.9500
S—C16	1.810 (2)	C11—C12	1.374 (3)
F—C12	1.359 (2)	C11—H11	0.9500
O1—C7	1.377 (2)	C12—C13	1.376 (3)
O1—C8	1.380 (2)	C13—C14	1.387 (2)
C1—C8	1.372 (2)	C13—H13	0.9500
C1—C2	1.448 (2)	C14—H14	0.9500
C2—C7	1.391 (2)	C15—H15A	0.9800
C2—C3	1.397 (2)	C15—H15B	0.9800
C3—C4	1.385 (2)	C15—H15C	0.9800
C3—H3	0.9500	C16—C17	1.518 (2)
C4—C5	1.402 (2)	C16—H16A	0.9900
C5—C6	1.388 (2)	C16—H16B	0.9900
C5—H5	0.9500	C17—H17A	0.9800
C6—C7	1.393 (2)	C17—H17B	0.9800
C6—C15	1.498 (2)	C17—H17C	0.9800
C8—C9	1.465 (2)

C4—Cl—O2ⁱ	167.20 (6)	C11—C10—H10	119.7
O2—S—C1	106.41 (7)	C9—C10—H10	119.7
O2—S—C16	107.18 (8)	C12—C11—C10	118.53 (16)
C1—S—C16	97.87 (7)	C12—C11—H11	120.7
C7—O1—C8	106.97 (11)	C10—C11—H11	120.7
C8—C1—C2	107.05 (12)	F—C12—C11	118.63 (16)
C8—C1—S	129.11 (11)	F—C12—C13	118.49 (16)
C2—C1—S	123.49 (11)	C11—C12—C13	122.88 (15)
C7—C2—C3	119.80 (13)	C12—C13—C14	118.44 (16)
C7—C2—C1	105.17 (13)	C12—C13—H13	120.8
C3—C2—C1	135.02 (14)	C14—C13—H13	120.8
C4—C3—C2	116.20 (14)	C13—C14—C9	120.75 (15)
C4—C3—H3	121.9	C13—C14—H14	119.6
C2—C3—H3	121.9	C9—C14—H14	119.6
C3—C4—C5	123.12 (14)	C6—C15—H15A	109.5
C3—C4—Cl	119.13 (12)	C6—C15—H15B	109.5
C5—C4—Cl	117.71 (12)	H15A—C15—H15B	109.5
C6—C5—C4	121.36 (14)	C6—C15—H15C	109.5
C6—C5—H5	119.3	H15A—C15—H15C	109.5
C4—C5—H5	119.3	H15B—C15—H15C	109.5
C5—C6—C7	114.70 (13)	C17—C16—S	110.04 (11)
C5—C6—C15	122.68 (14)	C17—C16—H16A	109.7
C7—C6—C15	122.61 (14)	S—C16—H16A	109.7
O1—C7—C2	110.59 (12)	C17—C16—H16B	109.7
O1—C7—C6	124.61 (13)	S—C16—H16B	109.7
C2—C7—C6	124.79 (14)	H16A—C16—H16B	108.2
C1—C8—O1	110.21 (12)	C16—C17—H17A	109.5
C1—C8—C9	135.48 (13)	C16—C17—H17B	109.5
O1—C8—C9	114.29 (12)	H17A—C17—H17B	109.5
C14—C9—C10	118.79 (14)	C16—C17—H17C	109.5
C14—C9—C8	119.28 (14)	H17A—C17—H17C	109.5
C10—C9—C8	121.92 (13)	H17B—C17—H17C	109.5
C11—C10—C9	120.58 (15)

9 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. An overview of halogen bonding.

Authors: Peter Politzer; Pat Lane; Monica C Concha; Yuguang Ma; Jane S Murray
Journal: J Mol Model Date: 2006-09-30 Impact factor: 1.810

5. 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

6. 5-Bromo-3-ethyl-sulfinyl-2-(4-fluoro-phenyl)-1-benzofuran.

Authors: Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-01-09

7. 5-Chloro-3-ethyl-sulfinyl-2-(4-fluoro-phen-yl)-1-benzofuran.

Authors: Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-01-20

8. 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

9. 3-Ethyl-sulfinyl-2-(4-fluoro-phen-yl)-5-iodo-7-methyl-1-benzofuran.

Authors: Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-02-13

9 in total

6 in total