2-(4-Fluoro-phen-yl)-3-methyl-sulfanyl-5-phenyl-1-benzofuran.

In the title compound, C(21)H(15)FOS, the 4-fluoro-phenyl ring is rotated out of the benzofuran plane, making a dihedral angle of 24.3 (1)°. The dihedral angle between the phenyl ring and the benzofuran plane is 28.3 (1)°. The crystal structure may be stabilized by two very weak aromatic π-π inter-actions between the furan and the benzene rings of neighbouring benzofuran systems; the centroid-centroid distances are 3.909 (4) and 4.028 (4) Å.

Related literature

For the crystal structures of similar 2,5-diaryl-3-methyl­sulfanyl-1-benzofuran derivatives, see: Choi, Seo et al. (2006 ▶); Choi, Woo et al. (2006 ▶). For natural products with benzofuran ring systems, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶); von Reuss & König (2004 ▶).

Experimental

Crystal data

C21H15FOS

M = 334.39

Monoclinic,

a = 10.621 (6) Å

b = 7.192 (4) Å

c = 11.642 (6) Å

β = 116.076 (5)°

V = 798.7 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 173 K

0.50 × 0.42 × 0.33 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.893, T max = 0.932

7602 measured reflections

3339 independent reflections

3147 reflections with I > 2σ(I)

R int = 0.095

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.133

S = 1.04

3339 reflections

218 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.44 e Å−3

Absolute structure: Flack (1983), 1362 Friedel pairs

Flack parameter: 0.00 (9)

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 I. DOI: 10.1107/S1600536809041713/vm2006sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041713/vm2006Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H15FOS	F(000) = 348
Mr = 334.39	Dx = 1.390 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5096 reflections
a = 10.621 (6) Å	θ = 3.4–27.5°
b = 7.192 (4) Å	µ = 0.22 mm−1
c = 11.642 (6) Å	T = 173 K
β = 116.076 (5)°	Block, colorless
V = 798.7 (8) Å3	0.50 × 0.42 × 0.33 mm
Z = 2

Bruker SMART APEXII CCD diffractometer	3339 independent reflections
Radiation source: Rotating Anode	3147 reflections with I > 2σ(I)
HELIOS	Rint = 0.095
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 2.0°
φ and ω scans	h = −12→13
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −9→9
Tmin = 0.893, Tmax = 0.932	l = −14→15
7602 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050	H-atom parameters constrained
wR(F2) = 0.133	w = 1/[σ2(Fo2) + (0.0945P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3339 reflections	Δρmax = 0.41 e Å−3
218 parameters	Δρmin = −0.43 e Å−3
1 restraint	Absolute structure: Flack (1983), 1362 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (9)

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	Uiso*/Ueq
S	0.55481 (6)	0.85482 (12)	0.86991 (5)	0.03285 (19)
F	1.25269 (13)	0.7897 (3)	1.00995 (14)	0.0411 (4)
O	0.63814 (15)	0.7920 (2)	0.57182 (13)	0.0245 (4)
C1	0.5612 (2)	0.8243 (3)	0.72327 (19)	0.0223 (5)
C2	0.4412 (2)	0.8143 (3)	0.60022 (19)	0.0227 (5)
C3	0.2962 (2)	0.8170 (3)	0.55929 (18)	0.0221 (5)
H3	0.2591	0.8309	0.6178	0.027*
C4	0.2085 (2)	0.7984 (3)	0.42913 (19)	0.0212 (4)
C5	0.2683 (2)	0.7823 (4)	0.3427 (2)	0.0260 (5)
H5	0.2089	0.7725	0.2558	0.031*
C6	0.4106 (2)	0.7804 (4)	0.38153 (19)	0.0251 (5)
H6	0.4485	0.7701	0.3234	0.030*
C7	0.4948 (2)	0.7947 (3)	0.5121 (2)	0.0230 (5)
C8	0.6759 (2)	0.8099 (3)	0.70145 (19)	0.0234 (5)
C9	0.8275 (2)	0.8059 (3)	0.78298 (19)	0.0229 (5)
C10	0.9163 (2)	0.7210 (4)	0.7396 (2)	0.0251 (5)
H10	0.8786	0.6685	0.6584	0.030*
C11	1.0589 (2)	0.7133 (4)	0.8147 (2)	0.0297 (5)
H11	1.1177	0.6548	0.7858	0.036*
C12	1.1119 (2)	0.7952 (4)	0.9344 (2)	0.0283 (5)
C13	1.0284 (2)	0.8825 (4)	0.9805 (2)	0.0290 (5)
H13	1.0674	0.9376	1.0610	0.035*
C14	0.8855 (2)	0.8868 (4)	0.9050 (2)	0.0262 (5)
H14	0.8273	0.9437	0.9352	0.031*
C15	0.05328 (19)	0.7926 (3)	0.38285 (19)	0.0219 (4)
C16	−0.0110 (2)	0.8798 (4)	0.4505 (2)	0.0260 (5)
H16	0.0430	0.9478	0.5238	0.031*
C17	−0.1552 (2)	0.8657 (4)	0.4092 (2)	0.0301 (5)
H17	−0.1969	0.9239	0.4551	0.036*
C18	−0.2363 (2)	0.7662 (4)	0.3008 (2)	0.0332 (6)
H18	−0.3322	0.7546	0.2748	0.040*
C19	−0.1752 (2)	0.6834 (4)	0.2304 (2)	0.0335 (6)
H19	−0.2304	0.6199	0.1554	0.040*
C20	−0.0313 (2)	0.6951 (4)	0.2718 (2)	0.0263 (5)
H20	0.0094	0.6373	0.2249	0.032*
C21	0.4797 (3)	0.6375 (5)	0.8842 (3)	0.0451 (7)
H21A	0.5406	0.5375	0.8863	0.068*
H21B	0.3899	0.6218	0.8123	0.068*
H21C	0.4686	0.6371	0.9617	0.068*

	U11	U22	U33	U12	U13	U23
S	0.0337 (3)	0.0481 (4)	0.0206 (3)	−0.0045 (3)	0.0155 (2)	−0.0065 (3)
F	0.0241 (7)	0.0489 (10)	0.0401 (8)	0.0020 (6)	0.0050 (6)	0.0013 (8)
O	0.0244 (7)	0.0326 (9)	0.0174 (7)	0.0000 (7)	0.0101 (6)	−0.0011 (7)
C1	0.0248 (9)	0.0243 (12)	0.0181 (9)	−0.0034 (8)	0.0097 (8)	−0.0029 (9)
C2	0.0292 (10)	0.0231 (13)	0.0178 (9)	−0.0019 (9)	0.0123 (8)	−0.0015 (9)
C3	0.0262 (10)	0.0230 (12)	0.0199 (9)	−0.0009 (9)	0.0127 (8)	−0.0004 (9)
C4	0.0249 (10)	0.0196 (11)	0.0198 (9)	0.0002 (8)	0.0105 (8)	0.0002 (9)
C5	0.0297 (11)	0.0273 (12)	0.0188 (9)	0.0010 (10)	0.0087 (8)	−0.0011 (9)
C6	0.0304 (11)	0.0310 (13)	0.0169 (9)	0.0000 (10)	0.0130 (9)	−0.0013 (9)
C7	0.0238 (9)	0.0257 (12)	0.0207 (10)	−0.0008 (9)	0.0110 (8)	−0.0001 (9)
C8	0.0299 (10)	0.0227 (12)	0.0184 (9)	−0.0013 (9)	0.0113 (8)	−0.0011 (9)
C9	0.0247 (10)	0.0226 (12)	0.0222 (10)	−0.0018 (9)	0.0112 (8)	0.0012 (9)
C10	0.0305 (11)	0.0223 (11)	0.0235 (10)	−0.0015 (9)	0.0129 (9)	−0.0022 (9)
C11	0.0285 (11)	0.0291 (13)	0.0359 (12)	0.0019 (9)	0.0181 (10)	−0.0006 (11)
C12	0.0218 (10)	0.0278 (12)	0.0288 (11)	−0.0005 (9)	0.0052 (9)	0.0057 (10)
C13	0.0320 (11)	0.0289 (14)	0.0212 (10)	−0.0020 (10)	0.0071 (9)	−0.0006 (10)
C14	0.0277 (10)	0.0261 (13)	0.0242 (10)	0.0002 (10)	0.0108 (8)	−0.0017 (10)
C15	0.0235 (10)	0.0198 (11)	0.0210 (9)	0.0013 (9)	0.0086 (8)	0.0031 (9)
C16	0.0293 (10)	0.0236 (12)	0.0247 (10)	0.0017 (10)	0.0115 (8)	0.0002 (10)
C17	0.0322 (11)	0.0289 (12)	0.0361 (12)	0.0054 (11)	0.0212 (9)	0.0021 (12)
C18	0.0218 (10)	0.0351 (14)	0.0408 (13)	0.0023 (9)	0.0121 (10)	0.0021 (12)
C19	0.0276 (11)	0.0355 (14)	0.0303 (12)	−0.0006 (10)	0.0062 (9)	−0.0035 (11)
C20	0.0283 (11)	0.0272 (12)	0.0240 (10)	0.0016 (9)	0.0119 (9)	−0.0038 (10)
C21	0.0473 (15)	0.056 (2)	0.0393 (15)	−0.0026 (14)	0.0255 (13)	0.0137 (14)

S—C1	1.752 (2)	C10—H10	0.9300
S—C21	1.795 (3)	C11—C12	1.384 (3)
F—C12	1.362 (2)	C11—H11	0.9300
O—C7	1.368 (3)	C12—C13	1.374 (3)
O—C8	1.387 (3)	C13—C14	1.380 (3)
C1—C8	1.353 (3)	C13—H13	0.9300
C1—C2	1.441 (3)	C14—H14	0.9300
C2—C7	1.381 (3)	C15—C20	1.396 (3)
C2—C3	1.398 (3)	C15—C16	1.397 (3)
C3—C4	1.393 (3)	C16—C17	1.393 (3)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.411 (3)	C17—C18	1.375 (4)
C4—C15	1.493 (3)	C17—H17	0.9300
C5—C6	1.374 (3)	C18—C19	1.384 (4)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.388 (3)	C19—C20	1.389 (3)
C6—H6	0.9300	C19—H19	0.9300
C8—C9	1.467 (3)	C20—H20	0.9300
C9—C10	1.391 (3)	C21—H21A	0.9600
C9—C14	1.403 (3)	C21—H21B	0.9600
C10—C11	1.378 (3)	C21—H21C	0.9600
C1—S—C21	100.97 (13)	C12—C11—H11	121.0
C7—O—C8	106.04 (16)	F—C12—C13	118.3 (2)
C8—C1—C2	106.57 (18)	F—C12—C11	118.9 (2)
C8—C1—S	128.05 (16)	C13—C12—C11	122.7 (2)
C2—C1—S	125.37 (15)	C12—C13—C14	118.6 (2)
C7—C2—C3	119.98 (19)	C12—C13—H13	120.7
C7—C2—C1	105.69 (18)	C14—C13—H13	120.7
C3—C2—C1	134.31 (19)	C13—C14—C9	120.4 (2)
C4—C3—C2	118.64 (19)	C13—C14—H14	119.8
C4—C3—H3	120.7	C9—C14—H14	119.8
C2—C3—H3	120.7	C20—C15—C16	118.23 (19)
C3—C4—C5	119.2 (2)	C20—C15—C4	120.47 (19)
C3—C4—C15	119.99 (19)	C16—C15—C4	121.28 (19)
C5—C4—C15	120.80 (19)	C17—C16—C15	120.5 (2)
C6—C5—C4	122.8 (2)	C17—C16—H16	119.7
C6—C5—H5	118.6	C15—C16—H16	119.7
C4—C5—H5	118.6	C18—C17—C16	120.4 (2)
C5—C6—C7	116.5 (2)	C18—C17—H17	119.8
C5—C6—H6	121.8	C16—C17—H17	119.8
C7—C6—H6	121.8	C17—C18—C19	120.0 (2)
O—C7—C2	110.71 (18)	C17—C18—H18	120.0
O—C7—C6	126.35 (19)	C19—C18—H18	120.0
C2—C7—C6	122.9 (2)	C18—C19—C20	120.0 (2)
C1—C8—O	110.98 (18)	C18—C19—H19	120.0
C1—C8—C9	134.7 (2)	C20—C19—H19	120.0
O—C8—C9	114.35 (18)	C19—C20—C15	120.9 (2)
C10—C9—C14	118.9 (2)	C19—C20—H20	119.5
C10—C9—C8	120.0 (2)	C15—C20—H20	119.5
C14—C9—C8	121.05 (19)	S—C21—H21A	109.5
C11—C10—C9	121.3 (2)	S—C21—H21B	109.5
C11—C10—H10	119.3	H21A—C21—H21B	109.5
C9—C10—H10	119.3	S—C21—H21C	109.5
C10—C11—C12	118.0 (2)	H21A—C21—H21C	109.5
C10—C11—H11	121.0	H21B—C21—H21C	109.5
C21—S—C1—C8	−113.4 (2)	C1—C8—C9—C10	155.3 (3)
C21—S—C1—C2	68.3 (2)	O—C8—C9—C10	−23.3 (3)
C8—C1—C2—C7	−0.2 (3)	C1—C8—C9—C14	−24.7 (4)
S—C1—C2—C7	178.46 (18)	O—C8—C9—C14	156.6 (2)
C8—C1—C2—C3	178.5 (3)	C14—C9—C10—C11	0.8 (4)
S—C1—C2—C3	−2.9 (4)	C8—C9—C10—C11	−179.3 (2)
C7—C2—C3—C4	0.4 (3)	C9—C10—C11—C12	−0.9 (4)
C1—C2—C3—C4	−178.1 (3)	C10—C11—C12—F	−179.8 (2)
C2—C3—C4—C5	−1.6 (3)	C10—C11—C12—C13	0.2 (4)
C2—C3—C4—C15	177.4 (2)	F—C12—C13—C14	−179.3 (2)
C3—C4—C5—C6	1.3 (4)	C11—C12—C13—C14	0.8 (4)
C15—C4—C5—C6	−177.7 (2)	C12—C13—C14—C9	−0.9 (4)
C4—C5—C6—C7	0.2 (4)	C10—C9—C14—C13	0.2 (4)
C8—O—C7—C2	0.2 (3)	C8—C9—C14—C13	−179.8 (2)
C8—O—C7—C6	−179.9 (2)	C3—C4—C15—C20	−150.9 (2)
C3—C2—C7—O	−178.9 (2)	C5—C4—C15—C20	28.0 (4)
C1—C2—C7—O	0.0 (3)	C3—C4—C15—C16	27.4 (3)
C3—C2—C7—C6	1.2 (4)	C5—C4—C15—C16	−153.6 (2)
C1—C2—C7—C6	−180.0 (2)	C20—C15—C16—C17	1.4 (4)
C5—C6—C7—O	178.6 (2)	C4—C15—C16—C17	−177.0 (2)
C5—C6—C7—C2	−1.5 (4)	C15—C16—C17—C18	−0.2 (4)
C2—C1—C8—O	0.3 (3)	C16—C17—C18—C19	−1.6 (4)
S—C1—C8—O	−178.31 (17)	C17—C18—C19—C20	2.3 (4)
C2—C1—C8—C9	−178.4 (3)	C18—C19—C20—C15	−1.2 (4)
S—C1—C8—C9	3.0 (4)	C16—C15—C20—C19	−0.7 (4)
C7—O—C8—C1	−0.3 (3)	C4—C15—C20—C19	177.7 (2)
C7—O—C8—C9	178.73 (19)