1-(4-Bromo-phen-yl)-2-(phenyl-sulfon-yl)ethanone.

The overall conformation of the title mol-ecule, C(14)H(11)BrO(3)S, is L-shaped, as seen in the value of the dihedral angle formed between the terminal benzene rings of 75.44 (13)°. The presence of C-H⋯O inter-actions leads to the formation of linear supra-molecular chains along the a-axis direction in the crystal structure. These are connected into supra-molecular arrays in the ab plane via C-H⋯π contacts.

Related literature

For the biological activity of sulphones, see: Garuti et al. (2002 ▶); Abdel-Aziz & Mekawey (2009 ▶); Abdel-Aziz et al. (2010 ▶). For the synthesis, see: Takahashi et al. (1986 ▶).

Experimental

Crystal data

C14H11BrO3S

M = 339.20

Triclinic,

a = 5.6467 (4) Å

b = 10.3597 (6) Å

c = 11.1934 (6) Å

α = 86.430 (5)°

β = 89.177 (5)°

γ = 83.763 (5)°

V = 649.64 (7) Å3

Z = 2

Cu Kα radiation

μ = 5.83 mm−1

T = 100 K

0.25 × 0.20 × 0.02 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.291, T max = 1.000

4181 measured reflections

2533 independent reflections

2396 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.108

S = 1.04

2533 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.69 e Å−3

Δρmin = −0.80 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/S1600536811036671/pv2446sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036671/pv2446Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036671/pv2446Isup3.cml

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

C14H11BrO3S	Z = 2
Mr = 339.20	F(000) = 340
Triclinic, P1	Dx = 1.734 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.5418 Å
a = 5.6467 (4) Å	Cell parameters from 2772 reflections
b = 10.3597 (6) Å	θ = 4.0–74.2°
c = 11.1934 (6) Å	µ = 5.83 mm−1
α = 86.430 (5)°	T = 100 K
β = 89.177 (5)°	Plate, light-brown
γ = 83.763 (5)°	0.25 × 0.20 × 0.02 mm
V = 649.64 (7) Å3

Agilent SuperNova Dual diffractometer with Atlas detector	2533 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2396 reflections with I > 2σ(I)
mirror	Rint = 0.034
Detector resolution: 10.4041 pixels mm-1	θmax = 74.4°, θmin = 4.0°
ω scan	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −12→6
Tmin = 0.291, Tmax = 1.000	l = −13→13
4181 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0821P)2 + 0.0577P] where P = (Fo2 + 2Fc2)/3
2533 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.69 e Å−3
0 restraints	Δρmin = −0.80 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
Br1	1.22639 (4)	0.85297 (2)	−0.03616 (2)	0.01909 (14)
S1	0.56382 (10)	0.30122 (6)	0.45101 (5)	0.01267 (17)
O1	0.3196 (3)	0.36055 (18)	0.44650 (17)	0.0179 (4)
O2	0.6741 (3)	0.27303 (18)	0.56677 (16)	0.0187 (4)
O3	0.5107 (3)	0.40819 (18)	0.19816 (16)	0.0193 (4)
C1	0.5826 (4)	0.1561 (2)	0.3754 (2)	0.0137 (5)
C2	0.7865 (5)	0.0678 (3)	0.3911 (2)	0.0168 (5)
H2	0.9129	0.0869	0.4399	0.020*
C3	0.8018 (5)	−0.0480 (3)	0.3345 (2)	0.0198 (5)
H3	0.9389	−0.1094	0.3449	0.024*
C4	0.6160 (5)	−0.0744 (3)	0.2624 (3)	0.0195 (5)
H4	0.6276	−0.1534	0.2228	0.023*
C5	0.4139 (5)	0.0141 (3)	0.2480 (2)	0.0178 (5)
H5	0.2877	−0.0051	0.1991	0.021*
C6	0.3948 (4)	0.1304 (2)	0.3045 (2)	0.0164 (5)
H6	0.2567	0.1911	0.2950	0.020*
C7	0.7509 (5)	0.4054 (2)	0.3716 (2)	0.0137 (5)
H7A	0.7601	0.4828	0.4182	0.016*
H7B	0.9134	0.3591	0.3678	0.016*
C8	0.6743 (4)	0.4514 (2)	0.2452 (2)	0.0147 (5)
C9	0.8097 (4)	0.5513 (2)	0.1824 (2)	0.0143 (5)
C10	1.0105 (5)	0.5959 (3)	0.2326 (2)	0.0158 (5)
H10	1.0623	0.5639	0.3103	0.019*
C11	1.1329 (5)	0.6872 (3)	0.1681 (2)	0.0173 (5)
H11	1.2680	0.7183	0.2016	0.021*
C12	1.0565 (5)	0.7321 (2)	0.0551 (2)	0.0162 (5)
C13	0.8565 (5)	0.6902 (3)	0.0040 (2)	0.0184 (5)
H13	0.8051	0.7228	−0.0736	0.022*
C14	0.7355 (5)	0.6008 (3)	0.0685 (2)	0.0181 (5)
H14	0.5984	0.5720	0.0349	0.022*

	U11	U22	U33	U12	U13	U23
Br1	0.0211 (2)	0.0184 (2)	0.01762 (19)	−0.00312 (12)	0.00239 (12)	0.00122 (12)
S1	0.0132 (3)	0.0128 (3)	0.0125 (3)	−0.0021 (2)	−0.0015 (2)	−0.0028 (2)
O1	0.0136 (9)	0.0173 (9)	0.0232 (9)	0.0003 (7)	0.0005 (7)	−0.0078 (7)
O2	0.0231 (10)	0.0203 (10)	0.0133 (9)	−0.0045 (7)	−0.0034 (7)	−0.0013 (7)
O3	0.0230 (9)	0.0170 (9)	0.0191 (9)	−0.0066 (7)	−0.0078 (7)	0.0003 (7)
C1	0.0163 (11)	0.0117 (11)	0.0139 (11)	−0.0044 (9)	0.0012 (9)	−0.0017 (8)
C2	0.0166 (12)	0.0173 (12)	0.0168 (12)	−0.0036 (10)	−0.0043 (9)	0.0008 (9)
C3	0.0198 (12)	0.0163 (13)	0.0226 (13)	0.0002 (10)	0.0012 (10)	0.0002 (10)
C4	0.0250 (14)	0.0144 (12)	0.0206 (12)	−0.0081 (10)	0.0056 (10)	−0.0046 (9)
C5	0.0178 (12)	0.0201 (13)	0.0171 (12)	−0.0075 (10)	0.0019 (9)	−0.0039 (9)
C6	0.0157 (12)	0.0164 (12)	0.0173 (12)	−0.0028 (9)	0.0001 (9)	−0.0009 (9)
C7	0.0151 (11)	0.0125 (11)	0.0138 (12)	−0.0026 (9)	−0.0024 (9)	−0.0011 (9)
C8	0.0169 (11)	0.0104 (11)	0.0164 (12)	0.0020 (9)	−0.0031 (9)	−0.0040 (9)
C9	0.0177 (12)	0.0108 (11)	0.0145 (12)	−0.0004 (9)	−0.0029 (9)	−0.0033 (9)
C10	0.0171 (12)	0.0169 (12)	0.0133 (11)	−0.0007 (9)	−0.0031 (9)	−0.0018 (9)
C11	0.0154 (12)	0.0182 (12)	0.0187 (13)	−0.0022 (9)	−0.0027 (9)	−0.0026 (10)
C12	0.0179 (12)	0.0145 (12)	0.0165 (12)	−0.0010 (9)	0.0019 (9)	−0.0039 (9)
C13	0.0228 (13)	0.0199 (13)	0.0125 (11)	−0.0011 (10)	−0.0052 (9)	−0.0012 (9)
C14	0.0183 (12)	0.0193 (12)	0.0175 (12)	−0.0035 (10)	−0.0058 (10)	−0.0031 (10)

Br1—C12	1.899 (3)	C6—H6	0.9500
S1—O2	1.4452 (19)	C7—C8	1.518 (3)
S1—O1	1.4478 (18)	C7—H7A	0.9900
S1—C1	1.763 (2)	C7—H7B	0.9900
S1—C7	1.781 (3)	C8—C9	1.489 (4)
O3—C8	1.210 (3)	C9—C14	1.397 (3)
C1—C6	1.392 (3)	C9—C10	1.407 (4)
C1—C2	1.396 (3)	C10—C11	1.391 (4)
C2—C3	1.386 (4)	C10—H10	0.9500
C2—H2	0.9500	C11—C12	1.379 (4)
C3—C4	1.393 (4)	C11—H11	0.9500
C3—H3	0.9500	C12—C13	1.395 (4)
C4—C5	1.389 (4)	C13—C14	1.372 (4)
C4—H4	0.9500	C13—H13	0.9500
C5—C6	1.388 (4)	C14—H14	0.9500
C5—H5	0.9500
O2—S1—O1	118.37 (11)	S1—C7—H7A	108.3
O2—S1—C1	108.48 (11)	C8—C7—H7B	108.3
O1—S1—C1	108.42 (11)	S1—C7—H7B	108.3
O2—S1—C7	104.73 (11)	H7A—C7—H7B	107.4
O1—S1—C7	109.49 (12)	O3—C8—C9	121.8 (2)
C1—S1—C7	106.77 (11)	O3—C8—C7	121.2 (2)
C6—C1—C2	121.6 (2)	C9—C8—C7	117.0 (2)
C6—C1—S1	120.05 (19)	C14—C9—C10	119.0 (2)
C2—C1—S1	118.32 (18)	C14—C9—C8	118.4 (2)
C3—C2—C1	119.1 (2)	C10—C9—C8	122.6 (2)
C3—C2—H2	120.5	C11—C10—C9	119.8 (2)
C1—C2—H2	120.5	C11—C10—H10	120.1
C2—C3—C4	119.9 (2)	C9—C10—H10	120.1
C2—C3—H3	120.1	C12—C11—C10	119.4 (2)
C4—C3—H3	120.1	C12—C11—H11	120.3
C5—C4—C3	120.4 (2)	C10—C11—H11	120.3
C5—C4—H4	119.8	C11—C12—C13	121.8 (2)
C3—C4—H4	119.8	C11—C12—Br1	120.0 (2)
C4—C5—C6	120.5 (2)	C13—C12—Br1	118.2 (2)
C4—C5—H5	119.7	C14—C13—C12	118.5 (2)
C6—C5—H5	119.7	C14—C13—H13	120.7
C5—C6—C1	118.5 (2)	C12—C13—H13	120.7
C5—C6—H6	120.8	C13—C14—C9	121.4 (2)
C1—C6—H6	120.8	C13—C14—H14	119.3
C8—C7—S1	115.92 (18)	C9—C14—H14	119.3
C8—C7—H7A	108.3
O2—S1—C1—C6	142.5 (2)	S1—C7—C8—O3	−7.5 (3)
O1—S1—C1—C6	12.8 (2)	S1—C7—C8—C9	172.60 (17)
C7—S1—C1—C6	−105.1 (2)	O3—C8—C9—C14	3.6 (3)
O2—S1—C1—C2	−36.0 (2)	C7—C8—C9—C14	−176.6 (2)
O1—S1—C1—C2	−165.7 (2)	O3—C8—C9—C10	−175.5 (3)
C7—S1—C1—C2	76.4 (2)	C7—C8—C9—C10	4.4 (3)
C6—C1—C2—C3	0.1 (4)	C14—C9—C10—C11	−0.6 (4)
S1—C1—C2—C3	178.6 (2)	C8—C9—C10—C11	178.4 (2)
C1—C2—C3—C4	0.5 (4)	C9—C10—C11—C12	−0.5 (4)
C2—C3—C4—C5	−0.8 (4)	C10—C11—C12—C13	1.1 (4)
C3—C4—C5—C6	0.5 (4)	C10—C11—C12—Br1	−178.25 (18)
C4—C5—C6—C1	0.1 (4)	C11—C12—C13—C14	−0.7 (4)
C2—C1—C6—C5	−0.4 (4)	Br1—C12—C13—C14	178.7 (2)
S1—C1—C6—C5	−178.86 (19)	C12—C13—C14—C9	−0.5 (4)
O2—S1—C7—C8	−179.65 (18)	C10—C9—C14—C13	1.1 (4)
O1—S1—C7—C8	−51.8 (2)	C8—C9—C14—C13	−178.0 (2)
C1—S1—C7—C8	65.4 (2)

Cg1 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7a···O1i	0.99	2.29	3.250 (3)	162
C7—H7b···O1ii	0.99	2.47	3.307 (3)	142
C4—H4···Cg1iii	0.95	2.87	3.708 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7a⋯O1i	0.99	2.29	3.250 (3)	162
C7—H7b⋯O1ii	0.99	2.47	3.307 (3)	142
C4—H4⋯Cg1iii	0.95	2.87	3.708 (3)	147

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