5-Bromo-3-(4-fluoro-phenyl-sulfon-yl)-2,7-dimethyl-1-benzofuran.

In the title compound, C(16)H(12)BrFO(3)S, the 4-fluoro-phenyl ring makes a dihedral angle of 72.35 (5)° with the mean plane [r.m.s. deviation = 0.008 (1) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked into [010] chains via two different inversion-generated pairs of C-H⋯O hydrogen bonds. The crystal structure also exhibits slipped π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.667 (2) Å and slippage = 1.341 (2) Å], and between the benzene and the furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.759 (2) Å and slippage = 0.757 (2) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010 ▶, 2012 ▶).

Experimental

Crystal data

C16H12BrFO3S

M = 383.23

Triclinic,

a = 8.0789 (1) Å

b = 9.2754 (2) Å

c = 11.3555 (2) Å

α = 71.283 (1)°

β = 72.645 (1)°

γ = 70.042 (1)°

V = 740.30 (2) Å3

Z = 2

Mo Kα radiation

μ = 2.94 mm−1

T = 173 K

0.29 × 0.21 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.527, T max = 0.746

14090 measured reflections

3680 independent reflections

3259 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.074

S = 1.02

3680 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.47 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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812043607/hb6977sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043607/hb6977Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043607/hb6977Isup3.cml

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

C16H12BrFO3S	Z = 2
Mr = 383.23	F(000) = 384
Triclinic, P1	Dx = 1.719 Mg m−3
Hall symbol: -P 1	Melting point = 472–473 K
a = 8.0789 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2754 (2) Å	Cell parameters from 6655 reflections
c = 11.3555 (2) Å	θ = 2.7–28.3°
α = 71.283 (1)°	µ = 2.94 mm−1
β = 72.645 (1)°	T = 173 K
γ = 70.042 (1)°	Block, colourless
V = 740.30 (2) Å3	0.29 × 0.21 × 0.18 mm

Bruker SMART APEXII CCD diffractometer	3680 independent reflections
Radiation source: rotating anode	3259 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.031
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 1.9°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
Tmin = 0.527, Tmax = 0.746	l = −15→15
14090 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)] = 0.028	Hydrogen site location: difference Fourier map
wR(F2) = 0.074	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0417P)2 + 0.237P] where P = (Fo2 + 2Fc2)/3
3680 reflections	(Δ/σ)max = 0.002
201 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.47 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	0.75349 (3)	0.10966 (3)	0.797351 (17)	0.03912 (8)
S1	0.48725 (5)	0.40486 (5)	0.29104 (4)	0.02342 (10)
F1	1.00247 (19)	0.77090 (18)	0.00357 (14)	0.0571 (4)
O1	0.75109 (17)	−0.04433 (15)	0.32764 (12)	0.0274 (3)
O2	0.40458 (16)	0.45572 (16)	0.40738 (11)	0.0286 (3)
O3	0.37705 (17)	0.41993 (16)	0.20642 (12)	0.0315 (3)
C1	0.6075 (2)	0.2081 (2)	0.33360 (16)	0.0242 (3)
C2	0.6733 (2)	0.1303 (2)	0.45008 (15)	0.0227 (3)
C3	0.6674 (2)	0.1745 (2)	0.55829 (16)	0.0251 (3)
H3	0.6078	0.2785	0.5692	0.030*
C4	0.7538 (2)	0.0574 (2)	0.64843 (16)	0.0271 (3)
C5	0.8430 (2)	−0.0963 (2)	0.63592 (17)	0.0285 (4)
H5	0.9010	−0.1707	0.7011	0.034*
C6	0.8486 (2)	−0.1426 (2)	0.52969 (17)	0.0268 (3)
C7	0.7611 (2)	−0.0248 (2)	0.44028 (16)	0.0243 (3)
C8	0.6581 (2)	0.0987 (2)	0.26428 (16)	0.0265 (3)
C9	0.9424 (3)	−0.3065 (2)	0.51205 (19)	0.0331 (4)
H9A	0.8612	−0.3460	0.4891	0.050*
H9B	0.9767	−0.3761	0.5915	0.050*
H9C	1.0506	−0.3045	0.4440	0.050*
C10	0.6362 (3)	0.1018 (3)	0.13857 (18)	0.0346 (4)
H10A	0.5784	0.2103	0.0967	0.052*
H10B	0.5610	0.0329	0.1499	0.052*
H10C	0.7547	0.0644	0.0858	0.052*
C11	0.6478 (2)	0.5107 (2)	0.20442 (16)	0.0244 (3)
C12	0.6821 (3)	0.5500 (2)	0.07255 (17)	0.0321 (4)
H12	0.6237	0.5157	0.0295	0.038*
C13	0.8014 (3)	0.6392 (3)	0.00442 (19)	0.0394 (5)
H13	0.8256	0.6685	−0.0859	0.047*
C14	0.8840 (3)	0.6845 (2)	0.0705 (2)	0.0376 (4)
C15	0.8550 (3)	0.6459 (3)	0.2007 (2)	0.0370 (4)
H15	0.9169	0.6782	0.2427	0.044*
C16	0.7330 (2)	0.5585 (2)	0.26933 (17)	0.0300 (4)
H16	0.7078	0.5316	0.3597	0.036*

	U11	U22	U33	U12	U13	U23
Br1	0.05355 (14)	0.04150 (14)	0.02493 (11)	−0.01030 (10)	−0.01583 (8)	−0.00744 (8)
S1	0.02474 (19)	0.0241 (2)	0.02165 (19)	−0.00430 (16)	−0.00808 (15)	−0.00546 (16)
F1	0.0558 (8)	0.0497 (9)	0.0620 (9)	−0.0322 (7)	−0.0040 (7)	0.0026 (7)
O1	0.0325 (6)	0.0237 (6)	0.0290 (6)	−0.0070 (5)	−0.0088 (5)	−0.0090 (5)
O2	0.0296 (6)	0.0290 (7)	0.0250 (6)	−0.0048 (5)	−0.0041 (5)	−0.0089 (5)
O3	0.0325 (6)	0.0346 (7)	0.0306 (6)	−0.0073 (6)	−0.0154 (5)	−0.0061 (6)
C1	0.0276 (8)	0.0232 (8)	0.0228 (7)	−0.0067 (7)	−0.0077 (6)	−0.0049 (7)
C2	0.0230 (7)	0.0222 (8)	0.0226 (7)	−0.0064 (6)	−0.0058 (6)	−0.0041 (6)
C3	0.0285 (8)	0.0234 (9)	0.0237 (8)	−0.0065 (7)	−0.0063 (6)	−0.0059 (7)
C4	0.0319 (8)	0.0303 (9)	0.0201 (7)	−0.0097 (7)	−0.0074 (6)	−0.0045 (7)
C5	0.0305 (8)	0.0260 (9)	0.0265 (8)	−0.0090 (7)	−0.0089 (7)	0.0009 (7)
C6	0.0271 (8)	0.0224 (9)	0.0294 (8)	−0.0091 (7)	−0.0058 (7)	−0.0020 (7)
C7	0.0262 (8)	0.0226 (9)	0.0253 (8)	−0.0075 (7)	−0.0055 (6)	−0.0061 (7)
C8	0.0277 (8)	0.0264 (9)	0.0267 (8)	−0.0077 (7)	−0.0062 (6)	−0.0075 (7)
C9	0.0357 (9)	0.0217 (9)	0.0397 (10)	−0.0056 (8)	−0.0106 (8)	−0.0047 (8)
C10	0.0431 (10)	0.0364 (11)	0.0302 (9)	−0.0093 (9)	−0.0125 (8)	−0.0132 (8)
C11	0.0267 (8)	0.0208 (8)	0.0235 (8)	−0.0034 (7)	−0.0072 (6)	−0.0041 (7)
C12	0.0360 (9)	0.0344 (10)	0.0253 (8)	−0.0077 (8)	−0.0113 (7)	−0.0041 (8)
C13	0.0435 (11)	0.0415 (12)	0.0254 (9)	−0.0122 (9)	−0.0071 (8)	0.0027 (8)
C14	0.0367 (10)	0.0264 (10)	0.0437 (11)	−0.0116 (8)	−0.0042 (8)	−0.0013 (9)
C15	0.0387 (10)	0.0345 (11)	0.0445 (11)	−0.0135 (9)	−0.0100 (8)	−0.0135 (9)
C16	0.0343 (9)	0.0305 (10)	0.0268 (8)	−0.0077 (8)	−0.0078 (7)	−0.0089 (8)

Br1—C4	1.9019 (16)	C6—C9	1.498 (3)
S1—O2	1.4396 (12)	C8—C10	1.480 (2)
S1—O3	1.4403 (12)	C9—H9A	0.9800
S1—C1	1.7354 (18)	C9—H9B	0.9800
S1—C11	1.7612 (17)	C9—H9C	0.9800
F1—C14	1.354 (2)	C10—H10A	0.9800
O1—C8	1.368 (2)	C10—H10B	0.9800
O1—C7	1.377 (2)	C10—H10C	0.9800
C1—C8	1.362 (2)	C11—C12	1.387 (2)
C1—C2	1.448 (2)	C11—C16	1.391 (2)
C2—C7	1.395 (2)	C12—C13	1.379 (3)
C2—C3	1.398 (2)	C12—H12	0.9500
C3—C4	1.382 (3)	C13—C14	1.371 (3)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.392 (3)	C14—C15	1.371 (3)
C5—C6	1.389 (2)	C15—C16	1.385 (3)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.383 (2)	C16—H16	0.9500
O2—S1—O3	119.77 (8)	C6—C9—H9A	109.5
O2—S1—C1	106.57 (8)	C6—C9—H9B	109.5
O3—S1—C1	108.82 (8)	H9A—C9—H9B	109.5
O2—S1—C11	107.04 (8)	C6—C9—H9C	109.5
O3—S1—C11	107.58 (8)	H9A—C9—H9C	109.5
C1—S1—C11	106.33 (8)	H9B—C9—H9C	109.5
C8—O1—C7	107.04 (13)	C8—C10—H10A	109.5
C8—C1—C2	107.36 (15)	C8—C10—H10B	109.5
C8—C1—S1	126.67 (13)	H10A—C10—H10B	109.5
C2—C1—S1	125.96 (13)	C8—C10—H10C	109.5
C7—C2—C3	119.41 (15)	H10A—C10—H10C	109.5
C7—C2—C1	104.63 (14)	H10B—C10—H10C	109.5
C3—C2—C1	135.96 (16)	C12—C11—C16	121.12 (16)
C4—C3—C2	115.86 (16)	C12—C11—S1	119.34 (13)
C4—C3—H3	122.1	C16—C11—S1	119.49 (13)
C2—C3—H3	122.1	C13—C12—C11	119.55 (17)
C3—C4—C5	123.81 (16)	C13—C12—H12	120.2
C3—C4—Br1	118.15 (14)	C11—C12—H12	120.2
C5—C4—Br1	118.04 (13)	C14—C13—C12	118.25 (18)
C6—C5—C4	121.09 (17)	C14—C13—H13	120.9
C6—C5—H5	119.5	C12—C13—H13	120.9
C4—C5—H5	119.5	F1—C14—C13	118.26 (19)
C7—C6—C5	114.69 (16)	F1—C14—C15	118.05 (19)
C7—C6—C9	122.24 (16)	C13—C14—C15	123.68 (18)
C5—C6—C9	123.06 (17)	C14—C15—C16	118.15 (18)
O1—C7—C6	124.43 (16)	C14—C15—H15	120.9
O1—C7—C2	110.43 (14)	C16—C15—H15	120.9
C6—C7—C2	125.14 (15)	C15—C16—C11	119.24 (17)
C1—C8—O1	110.54 (15)	C15—C16—H16	120.4
C1—C8—C10	134.51 (18)	C11—C16—H16	120.4
O1—C8—C10	114.95 (15)
O2—S1—C1—C8	157.48 (15)	C1—C2—C7—O1	−0.36 (18)
O3—S1—C1—C8	27.03 (18)	C3—C2—C7—C6	−1.2 (3)
C11—S1—C1—C8	−88.59 (17)	C1—C2—C7—C6	178.73 (16)
O2—S1—C1—C2	−22.76 (17)	C2—C1—C8—O1	0.24 (19)
O3—S1—C1—C2	−153.21 (14)	S1—C1—C8—O1	−179.96 (12)
C11—S1—C1—C2	91.18 (15)	C2—C1—C8—C10	−179.02 (19)
C8—C1—C2—C7	0.08 (18)	S1—C1—C8—C10	0.8 (3)
S1—C1—C2—C7	−179.73 (13)	C7—O1—C8—C1	−0.46 (19)
C8—C1—C2—C3	179.94 (19)	C7—O1—C8—C10	178.96 (15)
S1—C1—C2—C3	0.1 (3)	O2—S1—C11—C12	−147.79 (15)
C7—C2—C3—C4	0.8 (2)	O3—S1—C11—C12	−17.86 (17)
C1—C2—C3—C4	−179.07 (18)	C1—S1—C11—C12	98.59 (16)
C2—C3—C4—C5	0.1 (3)	O2—S1—C11—C16	29.83 (17)
C2—C3—C4—Br1	179.36 (12)	O3—S1—C11—C16	159.77 (14)
C3—C4—C5—C6	−0.8 (3)	C1—S1—C11—C16	−83.78 (16)
Br1—C4—C5—C6	179.98 (13)	C16—C11—C12—C13	−0.6 (3)
C4—C5—C6—C7	0.5 (2)	S1—C11—C12—C13	176.99 (16)
C4—C5—C6—C9	−179.85 (16)	C11—C12—C13—C14	0.8 (3)
C8—O1—C7—C6	−178.59 (16)	C12—C13—C14—F1	179.41 (19)
C8—O1—C7—C2	0.51 (18)	C12—C13—C14—C15	0.1 (3)
C5—C6—C7—O1	179.48 (15)	F1—C14—C15—C16	179.55 (18)
C9—C6—C7—O1	−0.2 (3)	C13—C14—C15—C16	−1.1 (3)
C5—C6—C7—C2	0.5 (2)	C14—C15—C16—C11	1.3 (3)
C9—C6—C7—C2	−179.19 (16)	C12—C11—C16—C15	−0.5 (3)
C3—C2—C7—O1	179.75 (14)	S1—C11—C16—C15	−178.04 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.95	2.53	3.408 (2)	154
C9—H9A···O2ii	0.98	2.50	3.304 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.95	2.53	3.408 (2)	154
C9—H9A⋯O2ii	0.98	2.50	3.304 (2)	139

Symmetry codes: (i) ; (ii) .