Literature DB >> 25309297

Crystal structure of 5-chloro-2-(3-fluoro-phen-yl)-3-methyl-sulfinyl-1-benzo-furan.

Abstract

In the title compound, C15H10ClFO2S, the dihedral angle between the plane of the benzo-furan ring system [r.m.s. deviation = 0.013 (1) Å] and that of the 3-fluoro-phenyl ring [r.m.s. deviation = 0.005 (1) Å] is 31.36 (5)°. In the crystal, mol-ecules are linked by two different pairs of C-H⋯O hydrogen bonds, forming inversion dimers.

Entities: Chemical Disease Gene

Keywords: 3-fluorophenyl; C—H⋯O hydrogen bonds; benzofuran; crystal structure

Year: 2014 PMID： 25309297 PMCID： PMC4186186 DOI： 10.1107/S1600536814017966

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

Related literature

For the pharmaceutical properties of compounds containing the benzofuran moiety, see: Aslam et al. (2009 ▶); Choi et al. (2003 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶); Ono et al. (2002 ▶). For natural products with a benzofuran ring, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the synthesis of the starting material 5-chloro-2-(3-fluorophenyl)-3-methylsulfanyl-1-benzofuran, see: Choi et al. (1999 ▶). For a related structure, see: Choi et al. (2009 ▶).

Experimental

Crystal data

C15H10ClFO2S M = 308.74 Triclinic, a = 8.0038 (1) Å b = 8.4322 (1) Å c = 10.6782 (2) Å α = 88.933 (1)° β = 81.008 (1)° γ = 66.859 (1)° V = 653.81 (2) Å3 Z = 2 Mo Kα radiation μ = 0.46 mm−1 T = 173 K 0.47 × 0.34 × 0.33 mm

Data collection

Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.813, T max = 0.863 11737 measured reflections 3124 independent reflections 2887 reflections with I > 2σ(I) R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.032 wR(F 2) = 0.086 S = 1.07 3124 reflections 182 parameters H-atom parameters constrained Δρmax = 0.30 e Å−3 Δρmin = −0.44 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. Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814017966/zq2226sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814017966/zq2226Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814017966/zq2226Isup3.cml Click here for additional data file. . DOI: 10.1107/S1600536814017966/zq2226fig1.tif 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. Click here for additional data file. x y z x y z . DOI: 10.1107/S1600536814017966/zq2226fig2.tif A view of the C—H⋯O hydrogen bonds (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 + 1]. CCDC reference: 1017893 Additional supporting information: crystallographic information; 3D view; checkCIF report

C₁₅H₁₀ClFO₂S	Z = 2
M_r = 308.74	F(000) = 316
Triclinic, P1	D_x = 1.568 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0038 (1) Å	Cell parameters from 6836 reflections
b = 8.4322 (1) Å	θ = 2.6–28.5°
c = 10.6782 (2) Å	µ = 0.46 mm⁻¹
α = 88.933 (1)°	T = 173 K
β = 81.008 (1)°	Block, colourless
γ = 66.859 (1)°	0.47 × 0.34 × 0.33 mm
V = 653.81 (2) Å³

Bruker SMART APEXII CCD diffractometer	3124 independent reflections
Radiation source: rotating anode	2887 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.022
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.0°, θ_min = 1.9°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
T_min = 0.813, T_max = 0.863	l = −14→13
11737 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)] = 0.032	Hydrogen site location: difference Fourier map
wR(F²) = 0.086	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0458P)² + 0.2424P] where P = (F_o² + 2F_c²)/3
3124 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Experimental. 1H NMR (δ p.p.m., CDCl3, 400 Hz): 8.23 (d, J = 2.04 Hz, 1H), 7.62 (d, J = 7.88 Hz, 1H), 7.54-7.58 (m, 1H), 7.45-7.52 (m, 2H), 7.38 (dd, J = 8.88 and 2.04 Hz, 1H), 7.16-7.22 (m, 1H), 3.11 (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.

	x	y	z	U_iso*/U_eq
Cl1	0.82187 (5)	−0.13963 (5)	−0.02027 (3)	0.03515 (11)
S1	0.21038 (4)	0.30346 (4)	0.39543 (3)	0.02300 (10)
F1	0.53226 (14)	0.29209 (13)	0.95736 (8)	0.0395 (2)
O1	0.70635 (13)	0.13881 (12)	0.49383 (9)	0.0234 (2)
O2	0.17787 (15)	0.16956 (13)	0.32625 (11)	0.0325 (2)
C1	0.44633 (17)	0.21871 (16)	0.40865 (12)	0.0210 (3)
C2	0.59652 (17)	0.10631 (16)	0.31628 (12)	0.0210 (3)
C3	0.61509 (18)	0.04393 (17)	0.19238 (13)	0.0231 (3)
H3	0.5120	0.0719	0.1499	0.028*
C4	0.79058 (19)	−0.06027 (18)	0.13484 (13)	0.0252 (3)
C5	0.94567 (19)	−0.10505 (18)	0.19490 (14)	0.0275 (3)
H5	1.0635	−0.1775	0.1510	0.033*
C6	0.92781 (19)	−0.04413 (18)	0.31773 (14)	0.0265 (3)
H6	1.0308	−0.0728	0.3605	0.032*
C7	0.75209 (18)	0.06058 (16)	0.37470 (13)	0.0221 (3)
C8	0.51944 (17)	0.23358 (16)	0.51261 (13)	0.0214 (3)
C9	0.44315 (18)	0.32961 (17)	0.63441 (12)	0.0216 (3)
C10	0.29269 (19)	0.48798 (18)	0.64645 (13)	0.0256 (3)
H10	0.2383	0.5349	0.5740	0.031*
C11	0.2218 (2)	0.57761 (18)	0.76298 (14)	0.0281 (3)
H11	0.1182	0.6846	0.7703	0.034*
C12	0.3016 (2)	0.51149 (19)	0.86908 (14)	0.0296 (3)
H12	0.2542	0.5717	0.9495	0.036*
C13	0.4517 (2)	0.35607 (19)	0.85427 (13)	0.0270 (3)
C14	0.52576 (18)	0.26207 (17)	0.74107 (13)	0.0235 (3)
H14	0.6293	0.1551	0.7350	0.028*
C15	0.2148 (2)	0.4624 (2)	0.28245 (17)	0.0365 (4)
H15A	0.3053	0.4062	0.2070	0.055*
H15B	0.2488	0.5481	0.3205	0.055*
H15C	0.0927	0.5199	0.2581	0.055*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0340 (2)	0.0413 (2)	0.02564 (19)	−0.01237 (16)	0.00258 (14)	−0.00911 (14)
S1	0.01657 (16)	0.02380 (17)	0.02762 (18)	−0.00635 (12)	−0.00525 (12)	0.00218 (12)
F1	0.0448 (6)	0.0467 (5)	0.0251 (4)	−0.0123 (4)	−0.0156 (4)	0.0027 (4)
O1	0.0190 (4)	0.0254 (5)	0.0236 (5)	−0.0056 (4)	−0.0057 (4)	−0.0006 (4)
O2	0.0296 (5)	0.0282 (5)	0.0451 (6)	−0.0133 (4)	−0.0166 (5)	0.0030 (4)
C1	0.0169 (6)	0.0214 (6)	0.0233 (6)	−0.0058 (5)	−0.0038 (5)	0.0009 (5)
C2	0.0181 (6)	0.0204 (6)	0.0238 (6)	−0.0069 (5)	−0.0034 (5)	0.0025 (5)
C3	0.0220 (6)	0.0244 (6)	0.0232 (6)	−0.0091 (5)	−0.0048 (5)	0.0016 (5)
C4	0.0268 (7)	0.0245 (6)	0.0236 (6)	−0.0104 (5)	−0.0008 (5)	−0.0017 (5)
C5	0.0206 (6)	0.0255 (6)	0.0316 (7)	−0.0058 (5)	0.0007 (5)	−0.0016 (5)
C6	0.0189 (6)	0.0257 (6)	0.0326 (7)	−0.0058 (5)	−0.0057 (5)	0.0008 (5)
C7	0.0213 (6)	0.0213 (6)	0.0233 (6)	−0.0077 (5)	−0.0045 (5)	0.0009 (5)
C8	0.0178 (6)	0.0201 (6)	0.0248 (6)	−0.0058 (5)	−0.0039 (5)	0.0021 (5)
C9	0.0205 (6)	0.0231 (6)	0.0226 (6)	−0.0099 (5)	−0.0044 (5)	0.0005 (5)
C10	0.0248 (7)	0.0250 (6)	0.0265 (7)	−0.0082 (5)	−0.0067 (5)	0.0018 (5)
C11	0.0252 (7)	0.0249 (6)	0.0306 (7)	−0.0065 (5)	−0.0026 (5)	−0.0036 (5)
C12	0.0303 (7)	0.0326 (7)	0.0259 (7)	−0.0132 (6)	−0.0019 (6)	−0.0052 (5)
C13	0.0296 (7)	0.0330 (7)	0.0231 (7)	−0.0155 (6)	−0.0095 (5)	0.0040 (5)
C14	0.0214 (6)	0.0246 (6)	0.0258 (7)	−0.0096 (5)	−0.0055 (5)	0.0017 (5)
C15	0.0326 (8)	0.0312 (7)	0.0499 (10)	−0.0138 (6)	−0.0176 (7)	0.0173 (7)

Cl1—C4	1.7418 (14)	C6—C7	1.3800 (19)
S1—O2	1.4866 (11)	C6—H6	0.9500
S1—C1	1.7652 (13)	C8—C9	1.4568 (18)
S1—C15	1.7937 (15)	C9—C10	1.3943 (18)
F1—C13	1.3584 (16)	C9—C14	1.4049 (18)
O1—C7	1.3724 (16)	C10—C11	1.385 (2)
O1—C8	1.3745 (15)	C10—H10	0.9500
C1—C8	1.3625 (18)	C11—C12	1.388 (2)
C1—C2	1.4439 (17)	C11—H11	0.9500
C2—C7	1.3945 (18)	C12—C13	1.377 (2)
C2—C3	1.3972 (18)	C12—H12	0.9500
C3—C4	1.3794 (19)	C13—C14	1.372 (2)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.402 (2)	C15—H15A	0.9800
C5—C6	1.383 (2)	C15—H15B	0.9800
C5—H5	0.9500	C15—H15C	0.9800

O2—S1—C1	107.08 (6)	C1—C8—C9	133.92 (12)
O2—S1—C15	105.95 (7)	O1—C8—C9	115.20 (11)
C1—S1—C15	97.48 (7)	C10—C9—C14	119.61 (12)
C7—O1—C8	106.62 (10)	C10—C9—C8	121.37 (12)
C8—C1—C2	106.92 (11)	C14—C9—C8	119.01 (12)
C8—C1—S1	126.40 (10)	C11—C10—C9	120.64 (13)
C2—C1—S1	126.42 (10)	C11—C10—H10	119.7
C7—C2—C3	119.41 (12)	C9—C10—H10	119.7
C7—C2—C1	105.03 (11)	C10—C11—C12	120.19 (13)
C3—C2—C1	135.54 (12)	C10—C11—H11	119.9
C4—C3—C2	116.67 (12)	C12—C11—H11	119.9
C4—C3—H3	121.7	C13—C12—C11	118.02 (13)
C2—C3—H3	121.7	C13—C12—H12	121.0
C3—C4—C5	123.22 (13)	C11—C12—H12	121.0
C3—C4—Cl1	118.56 (11)	F1—C13—C14	117.86 (13)
C5—C4—Cl1	118.22 (11)	F1—C13—C12	118.28 (13)
C6—C5—C4	120.30 (13)	C14—C13—C12	123.86 (13)
C6—C5—H5	119.8	C13—C14—C9	117.67 (12)
C4—C5—H5	119.8	C13—C14—H14	121.2
C7—C6—C5	116.25 (12)	C9—C14—H14	121.2
C7—C6—H6	121.9	S1—C15—H15A	109.5
C5—C6—H6	121.9	S1—C15—H15B	109.5
O1—C7—C6	125.27 (12)	H15A—C15—H15B	109.5
O1—C7—C2	110.56 (11)	S1—C15—H15C	109.5
C6—C7—C2	124.14 (13)	H15A—C15—H15C	109.5
C1—C8—O1	110.86 (11)	H15B—C15—H15C	109.5

O2—S1—C1—C8	−138.71 (12)	C1—C2—C7—C6	−178.69 (13)
C15—S1—C1—C8	112.01 (13)	C2—C1—C8—O1	0.06 (15)
O2—S1—C1—C2	34.63 (13)	S1—C1—C8—O1	174.46 (9)
C15—S1—C1—C2	−74.66 (13)	C2—C1—C8—C9	178.33 (14)
C8—C1—C2—C7	0.43 (14)	S1—C1—C8—C9	−7.3 (2)
S1—C1—C2—C7	−173.96 (10)	C7—O1—C8—C1	−0.54 (14)
C8—C1—C2—C3	−178.15 (15)	C7—O1—C8—C9	−179.16 (11)
S1—C1—C2—C3	7.5 (2)	C1—C8—C9—C10	−30.9 (2)
C7—C2—C3—C4	−0.39 (19)	O1—C8—C9—C10	147.27 (12)
C1—C2—C3—C4	178.04 (14)	C1—C8—C9—C14	150.28 (15)
C2—C3—C4—C5	0.4 (2)	O1—C8—C9—C14	−31.51 (17)
C2—C3—C4—Cl1	−179.30 (10)	C14—C9—C10—C11	−1.3 (2)
C3—C4—C5—C6	−0.2 (2)	C8—C9—C10—C11	179.97 (13)
Cl1—C4—C5—C6	179.54 (11)	C9—C10—C11—C12	0.9 (2)
C4—C5—C6—C7	−0.1 (2)	C10—C11—C12—C13	0.1 (2)
C8—O1—C7—C6	178.70 (13)	C11—C12—C13—F1	178.95 (13)
C8—O1—C7—C2	0.83 (14)	C11—C12—C13—C14	−0.6 (2)
C5—C6—C7—O1	−177.52 (12)	F1—C13—C14—C9	−179.35 (12)
C5—C6—C7—C2	0.1 (2)	C12—C13—C14—C9	0.2 (2)
C3—C2—C7—O1	178.08 (11)	C10—C9—C14—C13	0.7 (2)
C1—C2—C7—O1	−0.78 (15)	C8—C9—C14—C13	179.52 (12)
C3—C2—C7—C6	0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2ⁱ	0.95	2.57	3.3470 (18)	139
C14—H14···O2ⁱⁱ	0.95	2.59	3.4884 (17)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O2ⁱ	0.95	2.57	3.3470 (18)	139
C14—H14⋯O2ⁱⁱ	0.95	2.59	3.4884 (17)	157

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. Benzofuran derivatives as Abeta-aggregate-specific imaging agents for Alzheimer's disease.

Authors: Masahiro Ono; Mei-Ping Kung; Catherine Hou; Hank F Kung
Journal: Nucl Med Biol Date: 2002-08 Impact factor: 2.408

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

Authors: Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-10-03

6. Synthesis of 5-chloro-3-[4-(3-diethylaminopropoxy)benzoyl]-2-(4-methoxyphenyl)benzofuran as a beta-amyloid aggregation inhibitor.

Authors: Hong-Dae Choi; Pil-Ja Seo; Byeng-Wha Son; Byoung-Won Kang
Journal: Arch Pharm Res Date: 2003-12 Impact factor: 4.946

7. 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

8. Antibacterial and antifungal activity of cicerfuran and related 2-arylbenzofurans and stilbenes.

Authors: Shazia N Aslam; Philip C Stevenson; Tetsuo Kokubun; David R Hall
Journal: Microbiol Res Date: 2007-04-05 Impact factor: 5.415