1-(1-Benzofuran-2-yl)-2-(phenyl-sulfon-yl)ethanone.

The overall mol-ecular conformation of the title compound, C(16)H(12)O(4)S, is elongated, the dihedral angle formed between the benzofuran (r.m.s. deviation = 0.018 Å) and benzene rings being 24.81 (6)°. Both sulfonyl O atoms lie to one side of the S-bound benzene ring, and the carbonyl and furan O atoms are syn to each other. Supra-molecular arrays parallel to (101) sustained by C-H⋯O contacts feature in the crystal packing.

Related literature

For the biological activity of sulfones, see: Garuti et al. (2002 ▶), and of benzofuran, see: Abdel-Aziz & Mekawey (2009 ▶). For previous work on the chemistry and biological activity of benzofurans, see: Abdel-Wahab et al. (2009 ▶); Abdel-Aziz et al. (2009 ▶, 2011 ▶). For the synthesis, see: Takahashi et al. (1986 ▶).

Experimental

Crystal data

C16H12O4S

M = 300.32

Monoclinic,

a = 10.7560 (2) Å

b = 4.7855 (1) Å

c = 26.1838 (5) Å

β = 91.024 (2)°

V = 1347.54 (5) Å3

Z = 4

Cu Kα radiation

μ = 2.27 mm−1

T = 100 K

0.35 × 0.15 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.598, T max = 1.000

4617 measured reflections

2650 independent reflections

2495 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.086

S = 1.04

2650 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.47 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037366/pk2346sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037366/pk2346Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037366/pk2346Isup3.cml

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

C16H12O4S	F(000) = 624
Mr = 300.32	Dx = 1.480 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2yn	Cell parameters from 3182 reflections
a = 10.7560 (2) Å	θ = 3.4–74.0°
b = 4.7855 (1) Å	µ = 2.27 mm−1
c = 26.1838 (5) Å	T = 100 K
β = 91.024 (2)°	Prism, yellow
V = 1347.54 (5) Å3	0.35 × 0.15 × 0.15 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	2650 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2495 reflections with I > 2σ(I)
mirror	Rint = 0.016
Detector resolution: 10.4 pixels mm-1	θmax = 74.2°, θmin = 3.4°
ω scans	h = −12→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −5→3
Tmin = 0.598, Tmax = 1.000	l = −31→32
4617 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: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0498P)2 + 0.6486P] where P = (Fo2 + 2Fc2)/3
2650 reflections	(Δ/σ)max = 0.002
190 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
S1	0.53618 (3)	0.14747 (7)	0.735119 (11)	0.01251 (11)
O1	0.63911 (9)	−0.0313 (2)	0.74882 (4)	0.0174 (2)
O2	0.42375 (9)	0.0193 (2)	0.71500 (4)	0.0178 (2)
O3	0.64086 (10)	0.0614 (2)	0.62454 (4)	0.0228 (2)
O4	0.46617 (9)	0.2296 (2)	0.55532 (4)	0.0173 (2)
C1	0.49885 (13)	0.3575 (3)	0.78787 (5)	0.0137 (3)
C2	0.59334 (13)	0.4305 (3)	0.82217 (5)	0.0163 (3)
H2	0.6754	0.3613	0.8182	0.020*
C3	0.56524 (14)	0.6072 (3)	0.86253 (6)	0.0201 (3)
H3	0.6284	0.6594	0.8865	0.024*
C4	0.44511 (14)	0.7074 (3)	0.86776 (5)	0.0218 (3)
H4	0.4266	0.8293	0.8952	0.026*
C5	0.35163 (14)	0.6309 (3)	0.83320 (6)	0.0225 (3)
H5	0.2696	0.7000	0.8373	0.027*
C6	0.37766 (13)	0.4545 (3)	0.79284 (5)	0.0183 (3)
H6	0.3142	0.4008	0.7691	0.022*
C7	0.58626 (13)	0.3948 (3)	0.68830 (5)	0.0156 (3)
H7A	0.5339	0.5648	0.6894	0.019*
H7B	0.6737	0.4494	0.6953	0.019*
C8	0.57443 (13)	0.2571 (3)	0.63613 (5)	0.0159 (3)
C9	0.47739 (13)	0.3641 (3)	0.60172 (5)	0.0152 (3)
C10	0.39035 (13)	0.5678 (3)	0.60687 (5)	0.0166 (3)
H10	0.3806	0.6887	0.6353	0.020*
C11	0.31615 (13)	0.5640 (3)	0.56082 (5)	0.0166 (3)
C12	0.21147 (14)	0.7095 (3)	0.54235 (6)	0.0218 (3)
H12	0.1746	0.8536	0.5619	0.026*
C13	0.16361 (15)	0.6368 (3)	0.49482 (6)	0.0242 (3)
H13	0.0919	0.7305	0.4818	0.029*
C14	0.21907 (15)	0.4270 (3)	0.46533 (6)	0.0231 (3)
H14	0.1843	0.3841	0.4327	0.028*
C15	0.32250 (15)	0.2813 (3)	0.48237 (5)	0.0205 (3)
H15	0.3604	0.1402	0.4624	0.025*
C16	0.36750 (13)	0.3544 (3)	0.53055 (5)	0.0163 (3)

	U11	U22	U33	U12	U13	U23
S1	0.01469 (18)	0.01156 (19)	0.01124 (17)	−0.00044 (11)	−0.00085 (12)	−0.00152 (11)
O1	0.0191 (5)	0.0154 (5)	0.0178 (5)	0.0036 (4)	−0.0021 (4)	−0.0012 (4)
O2	0.0177 (5)	0.0180 (5)	0.0176 (5)	−0.0042 (4)	−0.0018 (4)	−0.0033 (4)
O3	0.0220 (5)	0.0289 (6)	0.0174 (5)	0.0066 (5)	−0.0021 (4)	−0.0065 (4)
O4	0.0208 (5)	0.0204 (5)	0.0106 (4)	0.0017 (4)	−0.0017 (4)	−0.0029 (4)
C1	0.0182 (7)	0.0128 (7)	0.0101 (6)	−0.0001 (5)	0.0012 (5)	0.0002 (5)
C2	0.0163 (6)	0.0180 (7)	0.0145 (6)	−0.0002 (5)	−0.0001 (5)	−0.0007 (5)
C3	0.0223 (7)	0.0234 (8)	0.0146 (7)	−0.0032 (6)	−0.0009 (5)	−0.0032 (6)
C4	0.0267 (8)	0.0233 (8)	0.0154 (7)	0.0009 (6)	0.0048 (6)	−0.0052 (6)
C5	0.0193 (7)	0.0267 (8)	0.0215 (7)	0.0046 (6)	0.0030 (6)	−0.0032 (6)
C6	0.0178 (7)	0.0209 (8)	0.0161 (7)	0.0009 (6)	−0.0010 (5)	0.0000 (6)
C7	0.0201 (7)	0.0150 (7)	0.0118 (6)	−0.0028 (5)	−0.0012 (5)	−0.0009 (5)
C8	0.0168 (6)	0.0187 (7)	0.0123 (6)	−0.0034 (5)	0.0007 (5)	−0.0015 (5)
C9	0.0192 (7)	0.0169 (7)	0.0096 (6)	−0.0041 (5)	0.0002 (5)	−0.0013 (5)
C10	0.0221 (7)	0.0159 (7)	0.0117 (6)	−0.0023 (6)	0.0018 (5)	0.0000 (5)
C11	0.0218 (7)	0.0155 (7)	0.0125 (6)	−0.0031 (6)	0.0011 (5)	0.0018 (5)
C12	0.0263 (8)	0.0209 (7)	0.0183 (7)	0.0029 (6)	0.0007 (6)	0.0028 (6)
C13	0.0256 (8)	0.0257 (9)	0.0211 (7)	0.0003 (6)	−0.0047 (6)	0.0076 (6)
C14	0.0307 (8)	0.0235 (8)	0.0149 (7)	−0.0059 (7)	−0.0061 (6)	0.0031 (6)
C15	0.0282 (8)	0.0196 (7)	0.0135 (7)	−0.0024 (6)	−0.0012 (6)	−0.0008 (6)
C16	0.0188 (7)	0.0170 (7)	0.0132 (6)	−0.0028 (5)	−0.0004 (5)	0.0027 (5)

S1—O1	1.4394 (10)	C7—C8	1.5201 (18)
S1—O2	1.4468 (10)	C7—H7A	0.9900
S1—C1	1.7603 (14)	C7—H7B	0.9900
S1—C7	1.7936 (15)	C8—C9	1.460 (2)
O3—C8	1.2193 (18)	C9—C10	1.360 (2)
O4—C16	1.3708 (17)	C10—C11	1.4343 (19)
O4—C9	1.3781 (16)	C10—H10	0.9500
C1—C2	1.3891 (19)	C11—C16	1.398 (2)
C1—C6	1.3919 (19)	C11—C12	1.403 (2)
C2—C3	1.391 (2)	C12—C13	1.383 (2)
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.387 (2)	C13—C14	1.406 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.390 (2)	C14—C15	1.380 (2)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.385 (2)	C15—C16	1.388 (2)
C5—H5	0.9500	C15—H15	0.9500
C6—H6	0.9500
O1—S1—O2	118.23 (6)	S1—C7—H7B	110.1
O1—S1—C1	109.21 (6)	H7A—C7—H7B	108.4
O2—S1—C1	109.08 (6)	O3—C8—C9	122.11 (13)
O1—S1—C7	108.87 (6)	O3—C8—C7	121.11 (13)
O2—S1—C7	106.87 (6)	C9—C8—C7	116.75 (12)
C1—S1—C7	103.59 (7)	C10—C9—O4	111.88 (12)
C16—O4—C9	105.58 (11)	C10—C9—C8	132.54 (13)
C2—C1—C6	122.09 (13)	O4—C9—C8	115.52 (12)
C2—C1—S1	118.46 (11)	C9—C10—C11	106.31 (13)
C6—C1—S1	119.40 (11)	C9—C10—H10	126.8
C1—C2—C3	118.55 (13)	C11—C10—H10	126.8
C1—C2—H2	120.7	C16—C11—C12	118.92 (13)
C3—C2—H2	120.7	C16—C11—C10	105.45 (13)
C4—C3—C2	120.04 (14)	C12—C11—C10	135.62 (14)
C4—C3—H3	120.0	C13—C12—C11	117.97 (15)
C2—C3—H3	120.0	C13—C12—H12	121.0
C5—C4—C3	120.60 (14)	C11—C12—H12	121.0
C5—C4—H4	119.7	C12—C13—C14	121.27 (15)
C3—C4—H4	119.7	C12—C13—H13	119.4
C4—C5—C6	120.23 (14)	C14—C13—H13	119.4
C4—C5—H5	119.9	C15—C14—C13	122.05 (14)
C6—C5—H5	119.9	C15—C14—H14	119.0
C5—C6—C1	118.49 (13)	C13—C14—H14	119.0
C5—C6—H6	120.8	C14—C15—C16	115.62 (14)
C1—C6—H6	120.8	C14—C15—H15	122.2
C8—C7—S1	107.86 (10)	C16—C15—H15	122.2
C8—C7—H7A	110.1	O4—C16—C15	125.07 (13)
S1—C7—H7A	110.1	O4—C16—C11	110.78 (12)
C8—C7—H7B	110.1	C15—C16—C11	124.14 (14)
O1—S1—C1—C2	29.99 (13)	O3—C8—C9—C10	176.92 (15)
O2—S1—C1—C2	160.57 (11)	C7—C8—C9—C10	−1.0 (2)
C7—S1—C1—C2	−85.89 (12)	O3—C8—C9—O4	−0.1 (2)
O1—S1—C1—C6	−152.63 (12)	C7—C8—C9—O4	−178.03 (11)
O2—S1—C1—C6	−22.06 (14)	O4—C9—C10—C11	0.70 (16)
C7—S1—C1—C6	91.48 (13)	C8—C9—C10—C11	−176.42 (15)
C6—C1—C2—C3	−0.3 (2)	C9—C10—C11—C16	−0.87 (16)
S1—C1—C2—C3	177.00 (11)	C9—C10—C11—C12	177.66 (16)
C1—C2—C3—C4	−0.2 (2)	C16—C11—C12—C13	0.3 (2)
C2—C3—C4—C5	0.5 (2)	C10—C11—C12—C13	−178.10 (16)
C3—C4—C5—C6	−0.3 (3)	C11—C12—C13—C14	−1.1 (2)
C4—C5—C6—C1	−0.2 (2)	C12—C13—C14—C15	0.8 (2)
C2—C1—C6—C5	0.5 (2)	C13—C14—C15—C16	0.4 (2)
S1—C1—C6—C5	−176.78 (12)	C9—O4—C16—C15	−179.32 (14)
O1—S1—C7—C8	84.82 (11)	C9—O4—C16—C11	−0.36 (15)
O2—S1—C7—C8	−43.93 (11)	C14—C15—C16—O4	177.59 (13)
C1—S1—C7—C8	−159.05 (10)	C14—C15—C16—C11	−1.2 (2)
S1—C7—C8—O3	−67.61 (16)	C12—C11—C16—O4	−178.05 (13)
S1—C7—C8—C9	110.33 (12)	C10—C11—C16—O4	0.77 (16)
C16—O4—C9—C10	−0.23 (15)	C12—C11—C16—C15	0.9 (2)
C16—O4—C9—C8	177.42 (12)	C10—C11—C16—C15	179.74 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3i	0.95	2.55	3.1808 (19)	124
C7—H7a···O2ii	0.99	2.57	3.5383 (17)	165
C7—H7b···O1i	0.99	2.47	3.3746 (17)	152
C15—H15···O3iii	0.95	2.47	3.2742 (17)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3i	0.95	2.55	3.1808 (19)	124
C7—H7a⋯O2ii	0.99	2.57	3.5383 (17)	165
C7—H7b⋯O1i	0.99	2.47	3.3746 (17)	152
C15—H15⋯O3iii	0.95	2.47	3.2742 (17)	142

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