Crystal structure of 2-meth-oxy-2-[(4-methyl-phen-yl)sulfan-yl]-1-phenyl-ethan-1-one.

In the title β-thio-carbonyl compound, C16H16O2S, the carbonyl and meth-oxy O atoms are approximately coplanar [O-C-C-O torsion angle = -18.2 (5)°] and syn to each other, and the tolyl ring is orientated to lie over them. The dihedral angle between the planes of the two rings is 44.03 (16)°. In the crystal, supra-molecular chains are formed along the c axis mediated by C-H⋯O inter-actions involving methine and methyl H atoms as donors, with the carbonyl O atom accepting both bonds; these pack with no specific inter-molecular inter-actions between them.

Related literature

For general background to β-thio­carbonyl and β-bis­(thio­carbon­yl) compounds, see: Vinhato et al. (2013 ▸); Zukerman-Schpector et al. (2008 ▸). For related structures, see: Olivato et al. (2013 ▸); Distefano et al. (1996 ▸). For further synthetic details, see: Ali & McDermott (2002 ▸); Zoretic & Soja (1976 ▸).

Experimental

Crystal data

C16H16O2S

M = 272.35

Orthorhombic,

a = 17.8579 (9) Å

b = 8.1257 (4) Å

c = 9.8317 (5) Å

V = 1426.66 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 293 K

0.41 × 0.14 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▸) T min = 0.690, T max = 0.745

5399 measured reflections

2337 independent reflections

1648 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.090

S = 1.02

2337 reflections

174 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack x determined using 552 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▸)

Absolute structure parameter: 0.02 (6)

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SIR (Burla et al., 2014 ▸; program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and DIAMOND (Brandenburg, 2006 ▸); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S205698901402550X/hg5421sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901402550X/hg5421Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S205698901402550X/hg5421Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S205698901402550X/hg5421fig1.tif

The mol­ecular structure of the title compound showing the atom-labelling scheme and displacement ellipsoids at the 35% probability level.

Click here for additional data file.

c . DOI: 10.1107/S205698901402550X/hg5421fig2.tif

A view of the supra­molecular chain along the c axis mediated by C—H⋯O inter­actions (bluee dashed lines).

Click here for additional data file.

c . DOI: 10.1107/S205698901402550X/hg5421fig3.tif

A view in projection down the c axis of the unit-cell contents. The C—H⋯O inter­actions are shown as blue dashed lines.

CCDC reference: 1035425

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H16O2S	Dx = 1.268 Mg m−3
Mr = 272.35	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 1023 reflections
a = 17.8579 (9) Å	θ = 3.1–18.7°
b = 8.1257 (4) Å	µ = 0.22 mm−1
c = 9.8317 (5) Å	T = 293 K
V = 1426.66 (12) Å3	Irregular, colourless
Z = 4	0.41 × 0.14 × 0.08 mm
F(000) = 576

Bruker APEXII CCD diffractometer	1648 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.031
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θmax = 25.4°, θmin = 2.8°
Tmin = 0.690, Tmax = 0.745	h = −21→21
5399 measured reflections	k = −9→9
2337 independent reflections	l = −10→11

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042	w = 1/[σ2(Fo2) + (0.0294P)2 + 0.2164P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.090	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.14 e Å−3
2337 reflections	Δρmin = −0.15 e Å−3
174 parameters	Absolute structure: Flack x determined using 552 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.02 (6)
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
C1	0.3662 (3)	0.6856 (7)	1.3764 (5)	0.0916 (18)
H1A	0.3249	0.7532	1.4046	0.137*
H1B	0.4106	0.7185	1.4243	0.137*
H1C	0.3553	0.5725	1.3964	0.137*
C2	0.3784 (3)	0.7055 (6)	1.2258 (5)	0.0642 (13)
C3	0.3285 (3)	0.7876 (6)	1.1440 (6)	0.0737 (14)
H3	0.2850	0.8300	1.1823	0.088*
C4	0.3411 (3)	0.8094 (6)	1.0061 (5)	0.0683 (13)
H4	0.3066	0.8670	0.9537	0.082*
C5	0.4049 (2)	0.7455 (5)	0.9462 (5)	0.0564 (11)
C6	0.4553 (2)	0.6622 (5)	1.0273 (5)	0.0615 (12)
H6	0.4987	0.6186	0.9893	0.074*
C7	0.4416 (3)	0.6434 (5)	1.1643 (5)	0.0635 (13)
H7	0.4763	0.5868	1.2171	0.076*
C8	0.4839 (2)	0.9437 (5)	0.7603 (5)	0.0576 (10)
H8	0.4930	0.9708	0.6646	0.069*
C9	0.6015 (3)	0.8116 (6)	0.7474 (6)	0.0834 (15)
H9A	0.6139	0.8637	0.6627	0.125*
H9B	0.5771	0.7085	0.7299	0.125*
H9C	0.6465	0.7927	0.7987	0.125*
C10	0.4468 (2)	1.0888 (5)	0.8275 (5)	0.0559 (11)
C11	0.3852 (2)	1.1782 (5)	0.7587 (5)	0.0539 (10)
C12	0.3573 (2)	1.3181 (5)	0.8205 (5)	0.0674 (13)
H12	0.3767	1.3519	0.9037	0.081*
C13	0.3007 (3)	1.4083 (5)	0.7595 (7)	0.0793 (14)
H13	0.2828	1.5027	0.8021	0.095*
C14	0.2709 (3)	1.3608 (6)	0.6381 (7)	0.0781 (14)
H14	0.2325	1.4212	0.5983	0.094*
C15	0.2984 (3)	1.2225 (7)	0.5754 (5)	0.0840 (16)
H15	0.2780	1.1887	0.4930	0.101*
C16	0.3556 (3)	1.1333 (6)	0.6325 (5)	0.0736 (13)
H16	0.3748	1.0423	0.5868	0.088*
O1	0.55239 (15)	0.9162 (4)	0.8235 (3)	0.0666 (9)
O2	0.46803 (18)	1.1328 (4)	0.9400 (3)	0.0727 (9)
S	0.41986 (7)	0.76542 (13)	0.76791 (16)	0.0711 (4)

	U11	U22	U33	U12	U13	U23
C1	0.090 (4)	0.115 (5)	0.070 (4)	−0.030 (3)	0.006 (3)	0.005 (3)
C2	0.065 (3)	0.064 (3)	0.064 (4)	−0.020 (2)	0.006 (3)	0.000 (3)
C3	0.061 (3)	0.077 (3)	0.084 (4)	−0.004 (3)	0.011 (3)	0.002 (3)
C4	0.064 (3)	0.064 (3)	0.077 (4)	−0.001 (2)	−0.007 (3)	0.006 (3)
C5	0.061 (3)	0.048 (2)	0.060 (3)	−0.011 (2)	−0.001 (2)	−0.003 (2)
C6	0.061 (3)	0.056 (3)	0.067 (3)	0.000 (2)	−0.001 (2)	−0.001 (3)
C7	0.066 (3)	0.058 (3)	0.066 (4)	−0.006 (2)	−0.008 (3)	0.009 (3)
C8	0.070 (3)	0.058 (2)	0.045 (2)	−0.0025 (19)	−0.003 (3)	0.003 (3)
C9	0.084 (3)	0.095 (3)	0.072 (4)	0.024 (3)	−0.003 (3)	0.000 (4)
C10	0.070 (3)	0.052 (3)	0.046 (3)	−0.009 (2)	0.007 (2)	0.002 (2)
C11	0.061 (2)	0.051 (2)	0.049 (3)	−0.0077 (18)	0.012 (3)	0.003 (3)
C12	0.066 (3)	0.065 (3)	0.071 (3)	−0.009 (2)	0.012 (3)	−0.013 (3)
C13	0.069 (3)	0.065 (3)	0.104 (4)	0.006 (2)	0.013 (4)	−0.008 (4)
C14	0.064 (3)	0.077 (3)	0.094 (4)	0.009 (3)	0.013 (3)	0.013 (3)
C15	0.085 (3)	0.102 (4)	0.065 (4)	0.014 (3)	−0.011 (3)	0.010 (3)
C16	0.090 (3)	0.078 (3)	0.053 (3)	0.017 (3)	−0.004 (3)	−0.007 (3)
O1	0.0665 (18)	0.077 (2)	0.057 (2)	0.0086 (16)	−0.0038 (16)	−0.0012 (16)
O2	0.094 (2)	0.076 (2)	0.048 (2)	−0.0017 (17)	−0.0047 (18)	−0.0078 (19)
S	0.0948 (8)	0.0600 (6)	0.0583 (7)	−0.0129 (6)	−0.0079 (8)	−0.0055 (8)

C1—C2	1.505 (7)	C8—H8	0.9800
C1—H1A	0.9600	C9—O1	1.432 (5)
C1—H1B	0.9600	C9—H9A	0.9600
C1—H1C	0.9600	C9—H9B	0.9600
C2—C3	1.373 (7)	C9—H9C	0.9600
C2—C7	1.376 (6)	C10—O2	1.224 (5)
C3—C4	1.385 (7)	C10—C11	1.480 (6)
C3—H3	0.9300	C11—C12	1.382 (6)
C4—C5	1.383 (6)	C11—C16	1.398 (7)
C4—H4	0.9300	C12—C13	1.384 (6)
C5—C6	1.379 (6)	C12—H12	0.9300
C5—S	1.781 (5)	C13—C14	1.363 (8)
C6—C7	1.378 (6)	C13—H13	0.9300
C6—H6	0.9300	C14—C15	1.373 (6)
C7—H7	0.9300	C14—H14	0.9300
C8—O1	1.390 (4)	C15—C16	1.372 (6)
C8—C10	1.505 (5)	C15—H15	0.9300
C8—S	1.847 (4)	C16—H16	0.9300
C2—C1—H1A	109.5	O1—C9—H9A	109.5
C2—C1—H1B	109.5	O1—C9—H9B	109.5
H1A—C1—H1B	109.5	H9A—C9—H9B	109.5
C2—C1—H1C	109.5	O1—C9—H9C	109.5
H1A—C1—H1C	109.5	H9A—C9—H9C	109.5
H1B—C1—H1C	109.5	H9B—C9—H9C	109.5
C3—C2—C7	116.9 (5)	O2—C10—C11	120.0 (4)
C3—C2—C1	122.3 (5)	O2—C10—C8	119.2 (4)
C7—C2—C1	120.8 (5)	C11—C10—C8	120.7 (4)
C2—C3—C4	122.0 (5)	C12—C11—C16	117.9 (4)
C2—C3—H3	119.0	C12—C11—C10	118.1 (4)
C4—C3—H3	119.0	C16—C11—C10	123.9 (4)
C5—C4—C3	120.2 (5)	C11—C12—C13	120.6 (5)
C5—C4—H4	119.9	C11—C12—H12	119.7
C3—C4—H4	119.9	C13—C12—H12	119.7
C6—C5—C4	118.4 (5)	C14—C13—C12	120.9 (5)
C6—C5—S	121.0 (4)	C14—C13—H13	119.5
C4—C5—S	120.6 (4)	C12—C13—H13	119.5
C7—C6—C5	120.2 (5)	C13—C14—C15	119.0 (5)
C7—C6—H6	119.9	C13—C14—H14	120.5
C5—C6—H6	119.9	C15—C14—H14	120.5
C2—C7—C6	122.3 (5)	C16—C15—C14	121.0 (5)
C2—C7—H7	118.8	C16—C15—H15	119.5
C6—C7—H7	118.8	C14—C15—H15	119.5
O1—C8—C10	108.5 (4)	C15—C16—C11	120.4 (5)
O1—C8—S	113.6 (3)	C15—C16—H16	119.8
C10—C8—S	108.9 (3)	C11—C16—H16	119.8
O1—C8—H8	108.6	C8—O1—C9	113.7 (3)
C10—C8—H8	108.6	C5—S—C8	101.8 (2)
S—C8—H8	108.6
C7—C2—C3—C4	−0.8 (7)	O2—C10—C11—C16	−177.7 (4)
C1—C2—C3—C4	178.2 (4)	C8—C10—C11—C16	2.3 (6)
C2—C3—C4—C5	1.0 (7)	C16—C11—C12—C13	1.2 (6)
C3—C4—C5—C6	−0.7 (6)	C10—C11—C12—C13	178.7 (4)
C3—C4—C5—S	177.5 (4)	C11—C12—C13—C14	0.5 (7)
C4—C5—C6—C7	0.3 (6)	C12—C13—C14—C15	−0.8 (7)
S—C5—C6—C7	−177.9 (4)	C13—C14—C15—C16	−0.6 (8)
C3—C2—C7—C6	0.3 (7)	C14—C15—C16—C11	2.4 (8)
C1—C2—C7—C6	−178.7 (4)	C12—C11—C16—C15	−2.7 (7)
C5—C6—C7—C2	0.0 (7)	C10—C11—C16—C15	180.0 (4)
O1—C8—C10—O2	−18.2 (5)	C10—C8—O1—C9	−164.3 (3)
S—C8—C10—O2	105.9 (4)	S—C8—O1—C9	74.4 (4)
O1—C8—C10—C11	161.7 (3)	C6—C5—S—C8	−83.1 (4)
S—C8—C10—C11	−74.1 (4)	C4—C5—S—C8	98.8 (4)
O2—C10—C11—C12	4.9 (6)	O1—C8—S—C5	63.2 (4)
C8—C10—C11—C12	−175.0 (4)	C10—C8—S—C5	−57.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O2i	0.96	2.49	3.366 (6)	152
C8—H8···O2ii	0.98	2.46	3.323 (6)	146

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C1H1BO2i	0.96	2.49	3.366(6)	152
C8H8O2ii	0.98	2.46	3.323(6)	146

Symmetry codes: (i) ; (ii) .