Literature DB >> 25484808

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

Abstract

In the title compound, C15H10F2O2S, the dihedral angle between the planes of the benzo-furan ring system [r.m.s. deviation = 0.015 (1) Å] and the 3-fluoro-phenyl ring is 26.60 (5)°. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯F hydrogen bonds, and by π-π inter-actions between the benzo-furan rings of inversion-related mol-ecules [centroid(benzene)-centroid(furan) distance = 3.819 (2) Å], forming a three-dimensional network.

Entities: Chemical Disease Gene

Keywords: 3-fluorophenyl; benzofuran; crystal structure; π–π interactions.

Year: 2014 PMID： 25484808 PMCID： PMC4257342 DOI： 10.1107/S160053681402251X

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

Related literature

For a related structure and background to benzofuran derivatives, see: Choi & Lee (2014 ▶). For further synthetic details, see: Choi et al. (1999 ▶).

Experimental

Crystal data

C15H10F2O2S M = 292.29 Monoclinic, a = 8.4826 (2) Å b = 16.6307 (4) Å c = 9.7493 (2) Å β = 113.756 (1)° V = 1258.81 (5) Å3 Z = 4 Mo Kα radiation μ = 0.28 mm−1 T = 173 K 0.62 × 0.55 × 0.42 mm

Data collection

Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.846, T max = 0.892 12021 measured reflections 3111 independent reflections 2736 reflections with I > 2σ(I) R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.036 wR(F 2) = 0.098 S = 1.03 3111 reflections 182 parameters H-atom parameters constrained Δρmax = 0.41 e Å−3 Δρmin = −0.35 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/S160053681402251X/fy2119sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681402251X/fy2119Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S160053681402251X/fy2119Isup3.cml Click here for additional data file. . DOI: 10.1107/S160053681402251X/fy2119fig1.tif 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. Click here for additional data file. x y z x y z x y z x y z x y z x y z x y z x y z . DOI: 10.1107/S160053681402251X/fy2119fig2.tif A view of the C—H⋯O, C—H⋯F and π–π interactions (dotted lines) in the crystal structure of the title compound. H atoms not participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) − x + 2, y − , − z + ; (ii) x − 1, y, z − 1; (iii) − x + 2, − y + 1, − z + 2; (iv) x, y, z + 1; (v) − x + 2, − y + 1, − z + 1; (vi) − x + 2, y + , − z + ; (vii) x + 1, y, z + 1; (viii) − x + 2, y + , − z + .] CCDC reference: 1029041 Additional supporting information: crystallographic information; 3D view; checkCIF report

C₁₅H₁₀F₂O₂S	F(000) = 600
M_r = 292.29	D_x = 1.542 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 460–459 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.4826 (2) Å	Cell parameters from 5007 reflections
b = 16.6307 (4) Å	θ = 2.5–28.3°
c = 9.7493 (2) Å	µ = 0.28 mm⁻¹
β = 113.756 (1)°	T = 173 K
V = 1258.81 (5) Å³	Block, colourless
Z = 4	0.62 × 0.55 × 0.42 mm

Bruker SMART APEXII CCD diffractometer	3111 independent reflections
Radiation source: rotating anode	2736 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.027
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 2.5°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −18→22
T_min = 0.846, T_max = 0.892	l = −12→12
12021 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)] = 0.036	Hydrogen site location: difference Fourier map
wR(F²) = 0.098	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0527P)² + 0.4861P] where P = (F_o² + 2F_c²)/3
3111 reflections	(Δ/σ)_max = 0.001
182 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Experimental. ¹H NMR (δ p.p.m., CDCl₃, 400 Hz): 7.91 (dd, J =8.56 and 2.40 Hz, 1H), 7.47-7.64 (m, 4H), 7.13-7.22 (m, 2H), 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
S1	0.68157 (5)	0.69175 (2)	0.61814 (4)	0.02500 (11)
F1	1.15704 (13)	0.43458 (6)	0.91143 (11)	0.0407 (3)
F2	0.31417 (14)	0.61447 (8)	−0.13611 (11)	0.0455 (3)
O1	0.66160 (13)	0.50305 (6)	0.36646 (11)	0.0228 (2)
O2	0.86399 (15)	0.71766 (7)	0.69804 (14)	0.0380 (3)
C1	0.68851 (17)	0.59646 (8)	0.54180 (15)	0.0206 (3)
C2	0.81117 (17)	0.53330 (8)	0.61313 (16)	0.0213 (3)
C3	0.93765 (18)	0.51943 (9)	0.75628 (16)	0.0257 (3)
H3	0.9568	0.5554	0.8371	0.031*
C4	1.03265 (19)	0.45056 (9)	0.77310 (17)	0.0284 (3)
C5	1.0128 (2)	0.39587 (9)	0.65947 (19)	0.0288 (3)
H5	1.0839	0.3494	0.6794	0.035*
C6	0.88870 (19)	0.40976 (8)	0.51726 (18)	0.0263 (3)
H6	0.8720	0.3742	0.4364	0.032*
C7	0.79001 (17)	0.47831 (8)	0.49901 (16)	0.0220 (3)
C8	0.60314 (17)	0.57525 (8)	0.39537 (15)	0.0207 (3)
C9	0.46688 (17)	0.61298 (8)	0.26667 (15)	0.0211 (3)
C10	0.34606 (18)	0.66392 (8)	0.28439 (16)	0.0231 (3)
H10	0.3529	0.6755	0.3821	0.028*
C11	0.21572 (19)	0.69790 (9)	0.16032 (17)	0.0263 (3)
H11	0.1338	0.7324	0.1737	0.032*
C12	0.20422 (19)	0.68181 (9)	0.01715 (17)	0.0280 (3)
H12	0.1159	0.7049	−0.0685	0.034*
C13	0.3254 (2)	0.63115 (10)	0.00347 (16)	0.0287 (3)
C14	0.45608 (19)	0.59613 (9)	0.12251 (17)	0.0262 (3)
H14	0.5368	0.5615	0.1076	0.031*
C15	0.6103 (2)	0.66132 (11)	0.7597 (2)	0.0377 (4)
H15A	0.6903	0.6213	0.8250	0.057*
H15B	0.4949	0.6378	0.7123	0.057*
H15C	0.6068	0.7082	0.8193	0.057*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0261 (2)	0.01759 (17)	0.02614 (19)	−0.00056 (12)	0.00519 (15)	−0.00347 (13)
F1	0.0340 (5)	0.0452 (6)	0.0317 (5)	0.0116 (4)	0.0017 (4)	0.0127 (4)
F2	0.0443 (6)	0.0705 (8)	0.0194 (5)	0.0076 (5)	0.0105 (4)	−0.0019 (4)
O1	0.0240 (5)	0.0197 (5)	0.0223 (5)	0.0023 (4)	0.0069 (4)	−0.0015 (4)
O2	0.0311 (6)	0.0311 (6)	0.0427 (7)	−0.0107 (5)	0.0055 (5)	−0.0085 (5)
C1	0.0204 (6)	0.0183 (6)	0.0215 (6)	0.0002 (5)	0.0068 (5)	0.0003 (5)
C2	0.0202 (6)	0.0192 (6)	0.0240 (7)	−0.0003 (5)	0.0086 (5)	0.0019 (5)
C3	0.0245 (7)	0.0262 (7)	0.0244 (7)	−0.0006 (6)	0.0077 (6)	0.0020 (5)
C4	0.0225 (7)	0.0312 (8)	0.0276 (7)	0.0027 (6)	0.0061 (6)	0.0099 (6)
C5	0.0258 (7)	0.0230 (7)	0.0395 (9)	0.0049 (5)	0.0152 (7)	0.0085 (6)
C6	0.0291 (7)	0.0198 (6)	0.0328 (8)	0.0017 (5)	0.0153 (6)	0.0017 (5)
C7	0.0221 (6)	0.0197 (6)	0.0238 (7)	−0.0004 (5)	0.0087 (6)	0.0021 (5)
C8	0.0207 (6)	0.0187 (6)	0.0229 (7)	0.0001 (5)	0.0090 (5)	−0.0007 (5)
C9	0.0188 (6)	0.0200 (6)	0.0224 (7)	−0.0024 (5)	0.0061 (5)	−0.0002 (5)
C10	0.0222 (6)	0.0252 (7)	0.0214 (6)	−0.0003 (5)	0.0081 (5)	−0.0001 (5)
C11	0.0228 (7)	0.0245 (7)	0.0303 (7)	0.0021 (5)	0.0092 (6)	0.0023 (6)
C12	0.0227 (7)	0.0314 (8)	0.0238 (7)	−0.0003 (6)	0.0030 (6)	0.0062 (6)
C13	0.0285 (7)	0.0371 (8)	0.0190 (7)	−0.0035 (6)	0.0081 (6)	−0.0009 (6)
C14	0.0243 (7)	0.0301 (7)	0.0240 (7)	0.0014 (5)	0.0095 (6)	−0.0021 (6)
C15	0.0439 (10)	0.0383 (9)	0.0378 (9)	0.0002 (7)	0.0237 (8)	−0.0091 (7)

S1—O2	1.4885 (12)	C6—C7	1.3828 (19)
S1—C1	1.7619 (14)	C6—H6	0.9500
S1—C15	1.7880 (17)	C8—C9	1.4614 (19)
F1—C4	1.3624 (17)	C9—C10	1.3930 (19)
F2—C13	1.3540 (17)	C9—C14	1.399 (2)
O1—C8	1.3710 (16)	C10—C11	1.388 (2)
O1—C7	1.3754 (17)	C10—H10	0.9500
C1—C8	1.3616 (19)	C11—C12	1.385 (2)
C1—C2	1.4444 (19)	C11—H11	0.9500
C2—C7	1.3949 (19)	C12—C13	1.377 (2)
C2—C3	1.395 (2)	C12—H12	0.9500
C3—C4	1.372 (2)	C13—C14	1.370 (2)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.390 (2)	C15—H15A	0.9800
C5—C6	1.381 (2)	C15—H15B	0.9800
C5—H5	0.9500	C15—H15C	0.9800

O2—S1—C1	106.07 (7)	C1—C8—C9	133.75 (12)
O2—S1—C15	106.34 (8)	O1—C8—C9	115.22 (11)
C1—S1—C15	98.65 (7)	C10—C9—C14	119.50 (13)
C8—O1—C7	106.50 (10)	C10—C9—C8	121.44 (12)
C8—C1—C2	106.99 (12)	C14—C9—C8	119.04 (12)
C8—C1—S1	125.57 (11)	C11—C10—C9	120.46 (13)
C2—C1—S1	126.22 (11)	C11—C10—H10	119.8
C7—C2—C3	119.31 (13)	C9—C10—H10	119.8
C7—C2—C1	104.86 (12)	C12—C11—C10	120.49 (13)
C3—C2—C1	135.77 (13)	C12—C11—H11	119.8
C4—C3—C2	115.84 (14)	C10—C11—H11	119.8
C4—C3—H3	122.1	C13—C12—C11	117.62 (13)
C2—C3—H3	122.1	C13—C12—H12	121.2
F1—C4—C3	117.68 (14)	C11—C12—H12	121.2
F1—C4—C5	117.26 (13)	F2—C13—C14	118.00 (14)
C3—C4—C5	125.05 (14)	F2—C13—C12	118.02 (14)
C6—C5—C4	119.27 (13)	C14—C13—C12	123.98 (14)
C6—C5—H5	120.4	C13—C14—C9	117.95 (13)
C4—C5—H5	120.4	C13—C14—H14	121.0
C5—C6—C7	116.38 (14)	C9—C14—H14	121.0
C5—C6—H6	121.8	S1—C15—H15A	109.5
C7—C6—H6	121.8	S1—C15—H15B	109.5
O1—C7—C6	125.23 (13)	H15A—C15—H15B	109.5
O1—C7—C2	110.61 (11)	S1—C15—H15C	109.5
C6—C7—C2	124.14 (14)	H15A—C15—H15C	109.5
C1—C8—O1	111.03 (12)	H15B—C15—H15C	109.5

O2—S1—C1—C8	−126.44 (13)	C1—C2—C7—C6	176.94 (13)
C15—S1—C1—C8	123.68 (13)	C2—C1—C8—O1	−0.09 (15)
O2—S1—C1—C2	39.24 (14)	S1—C1—C8—O1	167.87 (9)
C15—S1—C1—C2	−70.64 (14)	C2—C1—C8—C9	−179.62 (14)
C8—C1—C2—C7	0.90 (15)	S1—C1—C8—C9	−11.7 (2)
S1—C1—C2—C7	−166.96 (10)	C7—O1—C8—C1	−0.78 (15)
C8—C1—C2—C3	177.95 (15)	C7—O1—C8—C9	178.85 (11)
S1—C1—C2—C3	10.1 (2)	C1—C8—C9—C10	−28.6 (2)
C7—C2—C3—C4	−0.32 (19)	O1—C8—C9—C10	151.91 (12)
C1—C2—C3—C4	−177.04 (15)	C1—C8—C9—C14	152.70 (16)
C2—C3—C4—F1	−179.70 (12)	O1—C8—C9—C14	−26.82 (18)
C2—C3—C4—C5	0.8 (2)	C14—C9—C10—C11	0.0 (2)
F1—C4—C5—C6	−179.77 (13)	C8—C9—C10—C11	−178.75 (13)
C3—C4—C5—C6	−0.3 (2)	C9—C10—C11—C12	−0.2 (2)
C4—C5—C6—C7	−0.7 (2)	C10—C11—C12—C13	0.3 (2)
C8—O1—C7—C6	−176.95 (13)	C11—C12—C13—F2	179.38 (13)
C8—O1—C7—C2	1.38 (14)	C11—C12—C13—C14	−0.2 (2)
C5—C6—C7—O1	179.33 (13)	F2—C13—C14—C9	−179.58 (13)
C5—C6—C7—C2	1.2 (2)	C12—C13—C14—C9	0.0 (2)
C3—C2—C7—O1	−179.05 (11)	C10—C9—C14—C13	0.1 (2)
C1—C2—C7—O1	−1.41 (15)	C8—C9—C14—C13	178.89 (13)
C3—C2—C7—C6	−0.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2ⁱ	0.95	2.45	3.2612 (18)	143
C12—H12···O2ⁱⁱ	0.95	2.42	3.3361 (19)	161
C15—H15A···F1ⁱⁱⁱ	0.98	2.54	3.409 (2)	147
C15—H15B···F2^iv	0.98	2.55	3.163 (2)	121

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C5H5O2ⁱ	0.95	2.45	3.2612(18)	143
C12H12O2ⁱⁱ	0.95	2.42	3.3361(19)	161
C15H15AF1ⁱⁱⁱ	0.98	2.54	3.409(2)	147
C15H15BF2^iv	0.98	2.55	3.163(2)	121

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

2 in total

1. A short history of SHELX.

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

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

Authors: Hong Dae Choi; Uk Lee
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2014-08-09

2 in total