5-Bromo-2-(4-fluoro-phen-yl)-7-methyl-3-phenyl-sulfinyl-1-benzo-furan.

In the title compound, C21H14BrFO2S, the dihedral angles between the mean plane [r.m.s. deviation = 0.005 (1) Å] of the benzo-furan ring system and the pendant 4-fluoro-phenyl and phenyl rings are 1.50 (8) and 81.47 (6)°, respectively. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds into supra-molecular chains running along the a-axis direction. A short S⋯O contact [2.9623 (13) Å] involving the sulfinyl groups is observed between inversion-related chains.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2009 ▶); Seo et al. (2011 ▶). For details of sulfin­yl–sulfinyl inter­actions, see: Choi et al. (2008 ▶). For a review of carbon­yl–carbonyl inter­actions, see: Allen et al. (1998 ▶).

Experimental

Crystal data

C21H14BrFO2S

M = 429.29

Triclinic,

a = 7.9961 (2) Å

b = 10.6641 (2) Å

c = 11.1695 (2) Å

α = 71.980 (1)°

β = 74.694 (1)°

γ = 79.964 (1)°

V = 869.13 (3) Å3

Z = 2

Mo Kα radiation

μ = 2.51 mm−1

T = 173 K

0.30 × 0.24 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.523, T max = 0.665

20230 measured reflections

4315 independent reflections

3839 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.075

S = 1.05

4315 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.54 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) global, I. DOI: 10.1107/S1600536813016760/xu5714sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016760/xu5714Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016760/xu5714Isup3.cml

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

C21H14BrFO2S	Z = 2
Mr = 429.29	F(000) = 432
Triclinic, P1	Dx = 1.640 Mg m−3
Hall symbol: -P 1	Melting point = 485–486 K
a = 7.9961 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6641 (2) Å	Cell parameters from 9897 reflections
c = 11.1695 (2) Å	θ = 2.4–28.2°
α = 71.980 (1)°	µ = 2.51 mm−1
β = 74.694 (1)°	T = 173 K
γ = 79.964 (1)°	Block, colourless
V = 869.13 (3) Å3	0.30 × 0.24 × 0.18 mm

Bruker SMART APEXII CCD diffractometer	4315 independent reflections
Radiation source: rotating anode	3839 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.042
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 2.0°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
Tmin = 0.523, Tmax = 0.665	l = −14→14
20230 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)] = 0.029	Hydrogen site location: difference Fourier map
wR(F2) = 0.075	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0333P)2 + 0.4794P] where P = (Fo2 + 2Fc2)/3
4315 reflections	(Δ/σ)max = 0.003
236 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.54 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	Uiso*/Ueq
Br1	0.53307 (3)	0.21563 (2)	1.020561 (18)	0.03609 (8)
S1	0.37815 (5)	0.14799 (4)	0.52980 (4)	0.02275 (10)
F1	0.03254 (17)	0.61879 (13)	0.03936 (11)	0.0404 (3)
O1	0.26465 (16)	0.51907 (12)	0.55316 (11)	0.0224 (2)
O2	0.53338 (17)	0.07965 (13)	0.58227 (14)	0.0314 (3)
C1	0.3368 (2)	0.30250 (16)	0.56610 (16)	0.0210 (3)
C2	0.3727 (2)	0.32575 (17)	0.67753 (17)	0.0218 (3)
C3	0.4376 (2)	0.24909 (18)	0.78483 (17)	0.0245 (3)
H3	0.4730	0.1570	0.7975	0.029*
C4	0.4476 (2)	0.31452 (19)	0.87148 (17)	0.0266 (4)
C5	0.3997 (2)	0.44971 (19)	0.85545 (17)	0.0268 (4)
H5	0.4103	0.4888	0.9185	0.032*
C6	0.3367 (2)	0.52804 (18)	0.74877 (17)	0.0236 (3)
C7	0.3256 (2)	0.46035 (17)	0.66358 (16)	0.0217 (3)
C8	0.2727 (2)	0.42141 (16)	0.49445 (16)	0.0207 (3)
C9	0.2845 (3)	0.67413 (19)	0.7268 (2)	0.0319 (4)
H9A	0.2781	0.7145	0.6363	0.048*
H9B	0.3711	0.7146	0.7468	0.048*
H9C	0.1703	0.6887	0.7830	0.048*
C10	0.2095 (2)	0.46846 (17)	0.37493 (16)	0.0216 (3)
C11	0.2097 (2)	0.38651 (18)	0.29886 (17)	0.0264 (4)
H11	0.2505	0.2953	0.3251	0.032*
C12	0.1508 (3)	0.4366 (2)	0.18517 (18)	0.0287 (4)
H12	0.1520	0.3810	0.1328	0.034*
C13	0.0906 (2)	0.56897 (19)	0.15021 (17)	0.0274 (4)
C14	0.0875 (2)	0.65295 (19)	0.22250 (18)	0.0295 (4)
H14	0.0446	0.7437	0.1960	0.035*
C15	0.1482 (2)	0.60225 (18)	0.33472 (17)	0.0258 (4)
H15	0.1482	0.6592	0.3854	0.031*
C16	0.1908 (2)	0.07458 (17)	0.64136 (18)	0.0240 (3)
C17	0.2020 (3)	0.00195 (19)	0.7657 (2)	0.0320 (4)
H17	0.3086	−0.0096	0.7921	0.038*
C18	0.0577 (3)	−0.0536 (2)	0.8510 (2)	0.0418 (5)
H18	0.0643	−0.1030	0.9368	0.050*
C19	−0.0970 (3)	−0.0370 (2)	0.8114 (3)	0.0456 (6)
H19	−0.1967	−0.0747	0.8706	0.055*
C20	−0.1076 (3)	0.0339 (2)	0.6864 (3)	0.0451 (6)
H20	−0.2138	0.0444	0.6598	0.054*
C21	0.0378 (3)	0.0897 (2)	0.6001 (2)	0.0323 (4)
H21	0.0324	0.1376	0.5138	0.039*

	U11	U22	U33	U12	U13	U23
Br1	0.03889 (12)	0.04419 (13)	0.02697 (11)	−0.00605 (9)	−0.01581 (8)	−0.00429 (8)
S1	0.0246 (2)	0.0195 (2)	0.0269 (2)	0.00332 (16)	−0.00942 (17)	−0.01036 (16)
F1	0.0500 (7)	0.0448 (7)	0.0276 (6)	−0.0031 (6)	−0.0208 (5)	−0.0026 (5)
O1	0.0284 (6)	0.0190 (6)	0.0217 (6)	−0.0010 (5)	−0.0067 (5)	−0.0080 (5)
O2	0.0268 (6)	0.0291 (7)	0.0435 (8)	0.0083 (5)	−0.0169 (6)	−0.0160 (6)
C1	0.0225 (8)	0.0198 (8)	0.0220 (8)	−0.0013 (6)	−0.0052 (6)	−0.0078 (6)
C2	0.0198 (7)	0.0231 (8)	0.0241 (8)	−0.0029 (6)	−0.0045 (6)	−0.0088 (7)
C3	0.0234 (8)	0.0241 (8)	0.0263 (8)	−0.0025 (7)	−0.0070 (7)	−0.0063 (7)
C4	0.0241 (8)	0.0333 (10)	0.0228 (8)	−0.0071 (7)	−0.0073 (7)	−0.0045 (7)
C5	0.0267 (9)	0.0341 (10)	0.0237 (8)	−0.0087 (7)	−0.0028 (7)	−0.0132 (7)
C6	0.0230 (8)	0.0252 (9)	0.0248 (8)	−0.0069 (7)	−0.0013 (7)	−0.0108 (7)
C7	0.0227 (8)	0.0226 (8)	0.0202 (8)	−0.0042 (6)	−0.0041 (6)	−0.0062 (6)
C8	0.0218 (8)	0.0204 (8)	0.0216 (8)	−0.0022 (6)	−0.0033 (6)	−0.0096 (6)
C9	0.0400 (11)	0.0273 (9)	0.0325 (10)	−0.0052 (8)	−0.0068 (8)	−0.0142 (8)
C10	0.0202 (8)	0.0233 (8)	0.0197 (8)	−0.0020 (6)	−0.0028 (6)	−0.0055 (6)
C11	0.0302 (9)	0.0241 (9)	0.0251 (8)	−0.0003 (7)	−0.0082 (7)	−0.0068 (7)
C12	0.0325 (9)	0.0328 (10)	0.0244 (9)	−0.0046 (8)	−0.0080 (7)	−0.0108 (7)
C13	0.0260 (8)	0.0342 (10)	0.0194 (8)	−0.0041 (7)	−0.0069 (7)	−0.0016 (7)
C14	0.0305 (9)	0.0269 (9)	0.0263 (9)	0.0017 (7)	−0.0068 (7)	−0.0027 (7)
C15	0.0286 (9)	0.0237 (9)	0.0245 (8)	0.0002 (7)	−0.0054 (7)	−0.0080 (7)
C16	0.0263 (8)	0.0166 (8)	0.0320 (9)	0.0005 (6)	−0.0097 (7)	−0.0097 (7)
C17	0.0379 (10)	0.0236 (9)	0.0355 (10)	−0.0036 (8)	−0.0150 (8)	−0.0033 (8)
C18	0.0525 (13)	0.0287 (10)	0.0405 (12)	−0.0096 (10)	−0.0072 (10)	−0.0042 (9)
C19	0.0402 (12)	0.0361 (12)	0.0577 (15)	−0.0130 (10)	0.0039 (11)	−0.0166 (11)
C20	0.0289 (10)	0.0455 (13)	0.0706 (16)	−0.0040 (9)	−0.0139 (11)	−0.0275 (12)
C21	0.0320 (10)	0.0315 (10)	0.0406 (11)	0.0014 (8)	−0.0163 (8)	−0.0157 (8)

Br1—C4	1.9013 (18)	C9—H9C	0.9800
S1—O2	1.4899 (13)	C10—C11	1.394 (2)
S1—C1	1.7723 (17)	C10—C15	1.398 (2)
S1—C16	1.7972 (19)	C11—C12	1.388 (3)
S1—O2i	2.9623 (13)	C11—H11	0.9500
F1—C13	1.357 (2)	C12—C13	1.378 (3)
O1—C7	1.373 (2)	C12—H12	0.9500
O1—C8	1.377 (2)	C13—C14	1.372 (3)
C1—C8	1.368 (2)	C14—C15	1.382 (3)
C1—C2	1.448 (2)	C14—H14	0.9500
C2—C7	1.389 (2)	C15—H15	0.9500
C2—C3	1.396 (2)	C16—C17	1.383 (3)
C3—C4	1.381 (3)	C16—C21	1.384 (3)
C3—H3	0.9500	C17—C18	1.378 (3)
C4—C5	1.393 (3)	C17—H17	0.9500
C5—C6	1.388 (3)	C18—C19	1.387 (4)
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.388 (2)	C19—C20	1.383 (4)
C6—C9	1.501 (3)	C19—H19	0.9500
C8—C10	1.464 (2)	C20—C21	1.389 (3)
C9—H9A	0.9800	C20—H20	0.9500
C9—H9B	0.9800	C21—H21	0.9500
O2—S1—C1	105.07 (8)	C11—C10—C15	118.65 (16)
O2—S1—C16	107.03 (8)	C11—C10—C8	123.09 (16)
C1—S1—C16	97.33 (8)	C15—C10—C8	118.26 (15)
O2—S1—O2i	79.03 (6)	C12—C11—C10	120.80 (17)
C1—S1—O2i	169.13 (7)	C12—C11—H11	119.6
C16—S1—O2i	90.93 (6)	C10—C11—H11	119.6
C7—O1—C8	107.06 (13)	C13—C12—C11	118.30 (17)
C8—C1—C2	107.30 (14)	C13—C12—H12	120.8
C8—C1—S1	127.61 (13)	C11—C12—H12	120.8
C2—C1—S1	125.05 (13)	F1—C13—C14	118.48 (17)
C7—C2—C3	119.02 (16)	F1—C13—C12	118.73 (17)
C7—C2—C1	104.82 (15)	C14—C13—C12	122.80 (17)
C3—C2—C1	136.16 (16)	C13—C14—C15	118.36 (17)
C4—C3—C2	116.31 (16)	C13—C14—H14	120.8
C4—C3—H3	121.8	C15—C14—H14	120.8
C2—C3—H3	121.8	C14—C15—C10	121.08 (17)
C3—C4—C5	123.66 (17)	C14—C15—H15	119.5
C3—C4—Br1	118.48 (14)	C10—C15—H15	119.5
C5—C4—Br1	117.85 (13)	C17—C16—C21	121.00 (19)
C6—C5—C4	120.97 (16)	C17—C16—S1	119.87 (14)
C6—C5—H5	119.5	C21—C16—S1	119.11 (15)
C4—C5—H5	119.5	C18—C17—C16	119.7 (2)
C7—C6—C5	114.56 (16)	C18—C17—H17	120.2
C7—C6—C9	122.50 (17)	C16—C17—H17	120.2
C5—C6—C9	122.94 (16)	C17—C18—C19	119.8 (2)
O1—C7—C6	123.77 (15)	C17—C18—H18	120.1
O1—C7—C2	110.76 (14)	C19—C18—H18	120.1
C6—C7—C2	125.47 (16)	C20—C19—C18	120.6 (2)
C1—C8—O1	110.06 (15)	C20—C19—H19	119.7
C1—C8—C10	136.22 (16)	C18—C19—H19	119.7
O1—C8—C10	113.71 (14)	C19—C20—C21	119.7 (2)
C6—C9—H9A	109.5	C19—C20—H20	120.1
C6—C9—H9B	109.5	C21—C20—H20	120.1
H9A—C9—H9B	109.5	C16—C21—C20	119.2 (2)
C6—C9—H9C	109.5	C16—C21—H21	120.4
H9A—C9—H9C	109.5	C20—C21—H21	120.4
H9B—C9—H9C	109.5
O2—S1—C1—C8	146.26 (16)	S1—C1—C8—C10	3.3 (3)
C16—S1—C1—C8	−103.83 (17)	C7—O1—C8—C1	0.28 (18)
O2i—S1—C1—C8	35.4 (4)	C7—O1—C8—C10	179.29 (14)
O2—S1—C1—C2	−31.09 (17)	C1—C8—C10—C11	−2.7 (3)
C16—S1—C1—C2	78.82 (16)	O1—C8—C10—C11	178.64 (15)
O2i—S1—C1—C2	−142.0 (3)	C1—C8—C10—C15	178.07 (19)
C8—C1—C2—C7	0.15 (19)	O1—C8—C10—C15	−0.6 (2)
S1—C1—C2—C7	177.95 (13)	C15—C10—C11—C12	0.3 (3)
C8—C1—C2—C3	−180.0 (2)	C8—C10—C11—C12	−178.96 (17)
S1—C1—C2—C3	−2.2 (3)	C10—C11—C12—C13	−0.7 (3)
C7—C2—C3—C4	0.9 (2)	C11—C12—C13—F1	−179.89 (17)
C1—C2—C3—C4	−178.93 (19)	C11—C12—C13—C14	0.4 (3)
C2—C3—C4—C5	−1.0 (3)	F1—C13—C14—C15	−179.41 (16)
C2—C3—C4—Br1	179.48 (13)	C12—C13—C14—C15	0.3 (3)
C3—C4—C5—C6	0.3 (3)	C13—C14—C15—C10	−0.8 (3)
Br1—C4—C5—C6	179.83 (14)	C11—C10—C15—C14	0.5 (3)
C4—C5—C6—C7	0.4 (3)	C8—C10—C15—C14	179.73 (16)
C4—C5—C6—C9	−179.60 (17)	O2—S1—C16—C17	17.79 (17)
C8—O1—C7—C6	−179.86 (16)	C1—S1—C16—C17	−90.49 (15)
C8—O1—C7—C2	−0.18 (19)	O2i—S1—C16—C17	96.59 (15)
C5—C6—C7—O1	179.15 (15)	O2—S1—C16—C21	−160.92 (14)
C9—C6—C7—O1	−0.8 (3)	C1—S1—C16—C21	90.81 (15)
C5—C6—C7—C2	−0.5 (3)	O2i—S1—C16—C21	−82.11 (14)
C9—C6—C7—C2	179.53 (17)	C21—C16—C17—C18	−1.7 (3)
C3—C2—C7—O1	−179.89 (15)	S1—C16—C17—C18	179.67 (15)
C1—C2—C7—O1	0.02 (19)	C16—C17—C18—C19	0.5 (3)
C3—C2—C7—C6	−0.2 (3)	C17—C18—C19—C20	0.5 (3)
C1—C2—C7—C6	179.69 (17)	C18—C19—C20—C21	−0.4 (3)
C2—C1—C8—O1	−0.27 (19)	C17—C16—C21—C20	1.8 (3)
S1—C1—C8—O1	−178.00 (12)	S1—C16—C21—C20	−179.50 (15)
C2—C1—C8—C10	−178.96 (19)	C19—C20—C21—C16	−0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O2ii	0.95	2.33	3.280 (3)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O2i	0.95	2.33	3.280 (3)	176

Symmetry code: (i) .