2-Bromo-2-methyl-1-[4-(methyl-sulfan-yl)phen-yl]propan-1-one.

In the title compound, C(11)H(13)BrOS, the thio-ether unit and the phenyl ring adopt an essentially planar conformation, with a maximum deviation of 0.063 Å. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, extending in zigzag chains along the b axis. A weak intra-molecular C-H⋯Br hydrogen bond is also observed, which forms an S(6) ring motif.

Related literature

For general background to the properties of the title compound, a key inter­mediate for the preparation of a UV initiator, and its synthesis, see: Zhao et al. (2010 ▶); Liu et al. (2010 ▶). For related structures, see: Anuradha et al. (2008 ▶); Moreno-Fuquen et al. (2011 ▶).

Experimental

Crystal data

C11H13BrOS

M = 273.18

Monoclinic,

a = 11.061 (3) Å

b = 7.120 (2) Å

c = 14.721 (4) Å

β = 97.638 (3)°

V = 1149.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 3.73 mm−1

T = 153 K

0.27 × 0.23 × 0.18 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.433, T max = 0.551

9900 measured reflections

3625 independent reflections

2901 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.073

S = 1.00

3625 reflections

130 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.72 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812021472/bg2458sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021472/bg2458Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021472/bg2458Isup3.cml

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

C11H13BrOS	F(000) = 552
Mr = 273.18	Dx = 1.579 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4327 reflections
a = 11.061 (3) Å	θ = 2.2–31.0°
b = 7.120 (2) Å	µ = 3.73 mm−1
c = 14.721 (4) Å	T = 153 K
β = 97.638 (3)°	Block, colourless
V = 1149.1 (5) Å3	0.27 × 0.23 × 0.18 mm
Z = 4

Rigaku AFC10/Saturn724+ diffractometer	3625 independent reflections
Radiation source: Rotating Anode	2901 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 28.5714 pixels mm-1	θmax = 31.0°, θmin = 2.8°
phi and ω scans	h = −16→14
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −10→8
Tmin = 0.433, Tmax = 0.551	l = −21→21
9900 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) = 0.073	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0339P)2] where P = (Fo2 + 2Fc2)/3
3625 reflections	(Δ/σ)max = 0.001
130 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.72 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	0.327247 (17)	0.69311 (3)	0.037381 (13)	0.03062 (7)
S1	0.86419 (4)	0.48317 (6)	0.36691 (3)	0.02352 (10)
O1	0.25965 (11)	0.5378 (2)	0.26208 (9)	0.0358 (3)
C1	0.71222 (15)	0.4889 (2)	0.31441 (12)	0.0184 (3)
C2	0.62070 (15)	0.4850 (2)	0.37198 (12)	0.0211 (3)
H2	0.6426	0.4798	0.4366	0.025*
C3	0.49965 (15)	0.4886 (2)	0.33555 (12)	0.0213 (3)
H3	0.4389	0.4856	0.3755	0.026*
C4	0.46416 (15)	0.4968 (2)	0.24059 (11)	0.0186 (3)
C5	0.55563 (15)	0.5004 (2)	0.18392 (12)	0.0201 (3)
H5	0.5339	0.5061	0.1193	0.024*
C6	0.67786 (16)	0.4957 (2)	0.22041 (12)	0.0212 (3)
H6	0.7387	0.4972	0.1805	0.025*
C7	0.94956 (16)	0.4878 (3)	0.27138 (13)	0.0256 (4)
H7A	0.9245	0.3824	0.2303	0.031*
H7B	1.0368	0.4773	0.2937	0.031*
H7C	0.9340	0.6063	0.2380	0.031*
C8	0.33064 (16)	0.5063 (2)	0.20746 (12)	0.0214 (4)
C9	0.27806 (15)	0.4717 (2)	0.10720 (12)	0.0213 (4)
C10	0.13996 (16)	0.4720 (3)	0.09560 (14)	0.0325 (4)
H10A	0.1084	0.4581	0.0305	0.039*
H10B	0.1110	0.5908	0.1185	0.039*
H10C	0.1111	0.3673	0.1303	0.039*
C11	0.32472 (17)	0.2949 (2)	0.06566 (13)	0.0264 (4)
H11A	0.3003	0.1846	0.0987	0.032*
H11B	0.4139	0.2998	0.0705	0.032*
H11C	0.2900	0.2861	0.0010	0.032*

	U11	U22	U33	U12	U13	U23
Br1	0.03163 (12)	0.03130 (13)	0.02925 (11)	0.00122 (8)	0.00520 (8)	0.00951 (8)
S1	0.0197 (2)	0.0277 (2)	0.0229 (2)	0.00113 (17)	0.00177 (16)	−0.00186 (17)
O1	0.0213 (7)	0.0622 (10)	0.0251 (7)	0.0015 (7)	0.0078 (5)	−0.0100 (7)
C1	0.0189 (8)	0.0163 (8)	0.0201 (8)	0.0003 (6)	0.0028 (6)	−0.0008 (6)
C2	0.0234 (9)	0.0247 (9)	0.0155 (8)	0.0015 (7)	0.0036 (6)	−0.0007 (6)
C3	0.0230 (8)	0.0229 (9)	0.0194 (8)	0.0001 (7)	0.0077 (6)	−0.0014 (7)
C4	0.0193 (8)	0.0178 (8)	0.0193 (8)	0.0004 (6)	0.0054 (6)	−0.0005 (6)
C5	0.0213 (8)	0.0240 (9)	0.0158 (8)	−0.0008 (7)	0.0060 (6)	−0.0001 (6)
C6	0.0218 (8)	0.0230 (9)	0.0204 (8)	−0.0011 (7)	0.0085 (6)	0.0001 (7)
C7	0.0187 (8)	0.0266 (10)	0.0323 (10)	−0.0008 (7)	0.0063 (7)	0.0006 (8)
C8	0.0207 (8)	0.0234 (9)	0.0209 (8)	0.0004 (7)	0.0058 (6)	−0.0006 (7)
C9	0.0199 (8)	0.0253 (9)	0.0192 (8)	−0.0021 (7)	0.0047 (6)	0.0019 (7)
C10	0.0189 (9)	0.0487 (13)	0.0294 (10)	−0.0018 (8)	0.0018 (7)	0.0004 (9)
C11	0.0278 (10)	0.0273 (11)	0.0244 (9)	−0.0048 (7)	0.0045 (7)	−0.0039 (7)

Br1—C9	1.9962 (17)	C6—H6	0.9500
S1—C1	1.7548 (17)	C7—H7A	0.9800
S1—C7	1.7954 (19)	C7—H7B	0.9800
O1—C8	1.217 (2)	C7—H7C	0.9800
C1—C6	1.386 (2)	C8—C9	1.533 (2)
C1—C2	1.404 (2)	C9—C10	1.514 (2)
C2—C3	1.375 (2)	C9—C11	1.520 (2)
C2—H2	0.9500	C10—H10A	0.9800
C3—C4	1.402 (2)	C10—H10B	0.9800
C3—H3	0.9500	C10—H10C	0.9800
C4—C5	1.395 (2)	C11—H11A	0.9800
C4—C8	1.494 (2)	C11—H11B	0.9800
C5—C6	1.387 (2)	C11—H11C	0.9800
C5—H5	0.9500
C1—S1—C7	103.15 (9)	H7A—C7—H7C	109.5
C6—C1—C2	118.63 (16)	H7B—C7—H7C	109.5
C6—C1—S1	124.05 (13)	O1—C8—C4	119.29 (16)
C2—C1—S1	117.32 (13)	O1—C8—C9	118.05 (16)
C3—C2—C1	120.47 (16)	C4—C8—C9	122.63 (14)
C3—C2—H2	119.8	C10—C9—C11	110.31 (15)
C1—C2—H2	119.8	C10—C9—C8	110.88 (14)
C2—C3—C4	121.25 (15)	C11—C9—C8	114.50 (15)
C2—C3—H3	119.4	C10—C9—Br1	106.31 (12)
C4—C3—H3	119.4	C11—C9—Br1	108.46 (12)
C5—C4—C3	117.90 (16)	C8—C9—Br1	105.95 (11)
C5—C4—C8	124.62 (16)	C9—C10—H10A	109.5
C3—C4—C8	117.45 (14)	C9—C10—H10B	109.5
C6—C5—C4	121.01 (16)	H10A—C10—H10B	109.5
C6—C5—H5	119.5	C9—C10—H10C	109.5
C4—C5—H5	119.5	H10A—C10—H10C	109.5
C1—C6—C5	120.74 (15)	H10B—C10—H10C	109.5
C1—C6—H6	119.6	C9—C11—H11A	109.5
C5—C6—H6	119.6	C9—C11—H11B	109.5
S1—C7—H7A	109.5	H11A—C11—H11B	109.5
S1—C7—H7B	109.5	C9—C11—H11C	109.5
H7A—C7—H7B	109.5	H11A—C11—H11C	109.5
S1—C7—H7C	109.5	H11B—C11—H11C	109.5
C7—S1—C1—C6	−0.14 (17)	C4—C5—C6—C1	−0.5 (3)
C7—S1—C1—C2	179.45 (13)	C5—C4—C8—O1	−166.18 (16)
C6—C1—C2—C3	−0.2 (3)	C3—C4—C8—O1	12.1 (2)
S1—C1—C2—C3	−179.84 (13)	C5—C4—C8—C9	15.8 (3)
C1—C2—C3—C4	−0.2 (3)	C3—C4—C8—C9	−165.99 (15)
C2—C3—C4—C5	0.2 (3)	O1—C8—C9—C10	−3.6 (2)
C2—C3—C4—C8	−178.13 (15)	C4—C8—C9—C10	174.51 (16)
C3—C4—C5—C6	0.1 (2)	O1—C8—C9—C11	−129.15 (17)
C8—C4—C5—C6	178.36 (16)	C4—C8—C9—C11	48.9 (2)
C2—C1—C6—C5	0.6 (3)	O1—C8—C9—Br1	111.37 (16)
S1—C1—C6—C5	−179.83 (13)	C4—C8—C9—Br1	−70.55 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1i	0.98	2.47	3.359 (2)	150
C5—H5···Br1	0.95	2.78	3.387 (2)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O1i	0.98	2.47	3.359 (2)	150
C5—H5⋯Br1	0.95	2.78	3.387 (2)	123

Symmetry code: (i) .