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

In the title β-thio-carbonyl compound, C16H16O3S, the adjacent meth-oxy and carbonyl O atoms are synperiplanar [the O-C-C-O torsion angle is 19.8 (4)°] and are separated by 2.582 (3) Å. The dihedral angle between the rings is 40.11 (16)°, and the meth-oxy group is coplanar with the benzene ring to which it is connected [the C-C-O-C torsion angle is 179.1 (3)°]. The most notable feature of the crystal packing is the formation of methine and methyl C-H⋯O(carbon-yl) inter-actions that lead to a supra-molecular chain with a zigzag topology along the c axis. Chains pack with no specific inter-molecular inter-actions between them.

Related literature

For background to the present structural study, see: Vinhato et al. (2013 ▸); Zukerman-Schpector et al. (2008 ▸, 2015 ▸); Olivato et al. (2013 ▸); Distefano et al. (1996 ▸). For the structure of the methyl derivative, see: Zukerman-Schpector et al. (2015 ▸). For synthetic procedures, see: Ali & McDermott (2002 ▸); Zoretic & Soja (1976 ▸).

Experimental

Crystal data

C16H16O3S

M = 288.35

Orthorhombic,

a = 18.769 (3) Å

b = 7.643 (1) Å

c = 10.0578 (16) Å

V = 1442.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.37 × 0.16 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▸) T min = 0.618, T max = 0.745

6725 measured reflections

1935 independent reflections

1627 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.076

S = 1.04

1935 reflections

183 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.14 e Å−3

Absolute structure: Flack x determined using 418 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▸)

Absolute structure parameter: 0.09 (4)

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT (Bruker, 2009 ▸); program(s) used to solve structure: SIR (Burla et al., 2015 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); 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/S2056989015014565/hg5455sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015014565/hg5455Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015014565/hg5455Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015014565/hg5455fig1.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.

. DOI: 10.1107/S2056989015014565/hg5455fig2.tif

The supra­molecular chain in the title compound sustained by C—H⋯O inter­actions shown as orange dashed lines. Hydrogen atoms not participating in C—H⋯O inter­actions have been omitted for reasons of clarity.

Click here for additional data file.

c . DOI: 10.1107/S2056989015014565/hg5455fig3.tif

Unit-cell contents of the title compound shown in projection down the c axis. Inter­molecular C—H⋯O inter­actions are shown as orange dashed lines. One supra­molecular chain has been highlighted in space-filling mode.

CCDC reference: 1416521

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

C16H16O3S	Dx = 1.327 Mg m−3
Mr = 288.35	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 2745 reflections
a = 18.769 (3) Å	θ = 2.2–25.1°
b = 7.643 (1) Å	µ = 0.23 mm−1
c = 10.0578 (16) Å	T = 296 K
V = 1442.8 (4) Å3	Irregular, colourless
Z = 4	0.37 × 0.16 × 0.09 mm
F(000) = 608

Bruker APEXII CCD diffractometer	1627 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.026
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θmax = 25.4°, θmin = 2.2°
Tmin = 0.618, Tmax = 0.745	h = −22→22
6725 measured reflections	k = −8→9
1935 independent reflections	l = −7→12

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031	w = 1/[σ2(Fo2) + (0.0337P)2 + 0.2623P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.076	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.12 e Å−3
1935 reflections	Δρmin = −0.14 e Å−3
183 parameters	Absolute structure: Flack x determined using 418 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.09 (4)

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
S1	0.56536 (5)	0.23724 (10)	0.74255 (12)	0.0585 (3)
O1	0.53351 (13)	0.6345 (3)	0.9109 (3)	0.0608 (6)
O2	0.44516 (10)	0.4243 (3)	0.7959 (3)	0.0588 (6)
O3	0.67048 (13)	0.2149 (3)	1.2961 (3)	0.0702 (8)
C1	0.7294 (2)	0.8300 (5)	0.6168 (5)	0.0670 (11)
H1	0.7687	0.8842	0.5784	0.080*
C2	0.70618 (18)	0.8808 (4)	0.7391 (5)	0.0707 (11)
H2	0.7294	0.9710	0.7834	0.085*
C3	0.64887 (17)	0.8002 (4)	0.7975 (4)	0.0566 (9)
H3	0.6338	0.8355	0.8814	0.068*
C4	0.61332 (15)	0.6666 (4)	0.7325 (4)	0.0441 (7)
C5	0.63593 (19)	0.6186 (5)	0.6074 (4)	0.0587 (9)
H5	0.6117	0.5320	0.5608	0.070*
C6	0.6949 (2)	0.6995 (5)	0.5506 (4)	0.0696 (11)
H6	0.7108	0.6644	0.4672	0.083*
C7	0.55159 (15)	0.5857 (4)	0.8007 (3)	0.0439 (7)
C8	0.51146 (15)	0.4382 (3)	0.7343 (4)	0.0455 (7)
H8	0.5041	0.4685	0.6407	0.055*
C9	0.3949 (2)	0.3296 (5)	0.7185 (4)	0.0718 (12)
H9A	0.4129	0.2143	0.7012	0.108*
H9B	0.3871	0.3894	0.6358	0.108*
H9C	0.3507	0.3213	0.7663	0.108*
C10	0.59396 (18)	0.2334 (4)	0.9103 (4)	0.0448 (8)
C11	0.55035 (17)	0.1718 (4)	1.0103 (4)	0.0474 (8)
H11	0.5045	0.1348	0.9897	0.057*
C12	0.57361 (17)	0.1641 (4)	1.1405 (4)	0.0493 (9)
H12	0.5434	0.1230	1.2068	0.059*
C13	0.64116 (18)	0.2170 (4)	1.1714 (4)	0.0491 (9)
C14	0.68553 (18)	0.2783 (4)	1.0714 (4)	0.0610 (10)
H14	0.7316	0.3143	1.0919	0.073*
C15	0.66189 (18)	0.2860 (4)	0.9429 (4)	0.0550 (9)
H15	0.6921	0.3273	0.8767	0.066*
C16	0.6275 (2)	0.1561 (6)	1.4024 (4)	0.0749 (11)
H16A	0.6538	0.1639	1.4841	0.112*
H16B	0.6138	0.0367	1.3871	0.112*
H16C	0.5856	0.2277	1.4083	0.112*

	U11	U22	U33	U12	U13	U23
S1	0.0873 (6)	0.0513 (4)	0.0370 (5)	0.0083 (4)	−0.0003 (5)	−0.0065 (5)
O1	0.0732 (14)	0.0705 (15)	0.0387 (16)	0.0031 (13)	0.0019 (12)	−0.0129 (13)
O2	0.0561 (13)	0.0760 (15)	0.0444 (16)	−0.0089 (11)	0.0015 (13)	−0.0003 (13)
O3	0.0628 (15)	0.0992 (19)	0.0486 (18)	0.0162 (14)	−0.0127 (15)	0.0049 (15)
C1	0.056 (2)	0.067 (2)	0.078 (4)	−0.0075 (19)	−0.006 (2)	0.015 (2)
C2	0.061 (2)	0.061 (2)	0.090 (4)	−0.0085 (17)	−0.010 (3)	−0.010 (3)
C3	0.061 (2)	0.0537 (18)	0.055 (3)	0.0065 (17)	−0.007 (2)	−0.0090 (18)
C4	0.0491 (16)	0.0415 (14)	0.042 (2)	0.0075 (13)	−0.0069 (16)	−0.0003 (17)
C5	0.073 (2)	0.064 (2)	0.039 (2)	−0.0115 (18)	−0.0002 (19)	−0.0035 (18)
C6	0.075 (2)	0.083 (3)	0.051 (3)	−0.001 (2)	0.009 (2)	0.008 (2)
C7	0.0561 (17)	0.0455 (16)	0.030 (2)	0.0080 (14)	−0.0052 (17)	0.0020 (15)
C8	0.0552 (17)	0.0530 (16)	0.0282 (17)	−0.0006 (14)	−0.0009 (16)	0.0002 (18)
C9	0.070 (2)	0.081 (2)	0.065 (3)	−0.020 (2)	−0.009 (2)	0.002 (2)
C10	0.0572 (19)	0.0356 (16)	0.041 (2)	0.0100 (14)	0.0040 (16)	−0.0001 (15)
C11	0.0507 (18)	0.0478 (18)	0.044 (2)	−0.0021 (14)	0.0007 (16)	0.0018 (16)
C12	0.0536 (19)	0.0496 (19)	0.045 (2)	0.0071 (15)	0.0068 (16)	0.0041 (16)
C13	0.053 (2)	0.055 (2)	0.040 (2)	0.0139 (16)	−0.0016 (18)	0.0033 (16)
C14	0.0455 (18)	0.075 (2)	0.063 (3)	0.0020 (17)	−0.004 (2)	0.008 (2)
C15	0.055 (2)	0.060 (2)	0.050 (3)	0.0023 (17)	0.0125 (19)	0.0059 (18)
C16	0.083 (2)	0.103 (3)	0.039 (3)	0.027 (3)	−0.001 (2)	0.005 (2)

S1—C10	1.771 (4)	C7—C8	1.511 (4)
S1—C8	1.841 (3)	C8—H8	0.9800
O1—C7	1.217 (4)	C9—H9A	0.9600
O2—C8	1.394 (3)	C9—H9B	0.9600
O2—C9	1.421 (4)	C9—H9C	0.9600
O3—C13	1.370 (4)	C10—C15	1.376 (5)
O3—C16	1.413 (5)	C10—C11	1.380 (5)
C1—C2	1.361 (6)	C11—C12	1.381 (5)
C1—C6	1.363 (6)	C11—H11	0.9300
C1—H1	0.9300	C12—C13	1.367 (5)
C2—C3	1.372 (5)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.387 (5)
C3—C4	1.384 (4)	C14—C15	1.368 (6)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.377 (5)	C15—H15	0.9300
C4—C7	1.482 (4)	C16—H16A	0.9600
C5—C6	1.390 (5)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600
C6—H6	0.9300
C10—S1—C8	102.90 (15)	O2—C9—H9A	109.5
C8—O2—C9	112.8 (3)	O2—C9—H9B	109.5
C13—O3—C16	117.8 (3)	H9A—C9—H9B	109.5
C2—C1—C6	119.8 (4)	O2—C9—H9C	109.5
C2—C1—H1	120.1	H9A—C9—H9C	109.5
C6—C1—H1	120.1	H9B—C9—H9C	109.5
C1—C2—C3	120.7 (4)	C15—C10—C11	118.4 (3)
C1—C2—H2	119.7	C15—C10—S1	120.2 (3)
C3—C2—H2	119.7	C11—C10—S1	121.4 (3)
C2—C3—C4	120.4 (4)	C10—C11—C12	121.2 (3)
C2—C3—H3	119.8	C10—C11—H11	119.4
C4—C3—H3	119.8	C12—C11—H11	119.4
C5—C4—C3	118.6 (3)	C13—C12—C11	119.8 (3)
C5—C4—C7	123.6 (3)	C13—C12—H12	120.1
C3—C4—C7	117.8 (3)	C11—C12—H12	120.1
C4—C5—C6	120.2 (4)	C12—C13—O3	125.3 (3)
C4—C5—H5	119.9	C12—C13—C14	119.5 (4)
C6—C5—H5	119.9	O3—C13—C14	115.2 (3)
C1—C6—C5	120.2 (4)	C15—C14—C13	120.3 (4)
C1—C6—H6	119.9	C15—C14—H14	119.8
C5—C6—H6	119.9	C13—C14—H14	119.8
O1—C7—C4	120.8 (3)	C14—C15—C10	120.8 (3)
O1—C7—C8	119.4 (3)	C14—C15—H15	119.6
C4—C7—C8	119.8 (3)	C10—C15—H15	119.6
O2—C8—C7	107.8 (2)	O3—C16—H16A	109.5
O2—C8—S1	114.0 (2)	O3—C16—H16B	109.5
C7—C8—S1	109.2 (2)	H16A—C16—H16B	109.5
O2—C8—H8	108.6	O3—C16—H16C	109.5
C7—C8—H8	108.6	H16A—C16—H16C	109.5
S1—C8—H8	108.6	H16B—C16—H16C	109.5
C6—C1—C2—C3	0.9 (6)	C4—C7—C8—S1	74.1 (3)
C1—C2—C3—C4	−0.5 (5)	C10—S1—C8—O2	−74.0 (3)
C2—C3—C4—C5	−1.1 (5)	C10—S1—C8—C7	46.6 (3)
C2—C3—C4—C7	−179.6 (3)	C8—S1—C10—C15	−101.2 (3)
C3—C4—C5—C6	2.2 (5)	C8—S1—C10—C11	81.4 (3)
C7—C4—C5—C6	−179.3 (3)	C15—C10—C11—C12	0.6 (4)
C2—C1—C6—C5	0.2 (6)	S1—C10—C11—C12	178.0 (2)
C4—C5—C6—C1	−1.9 (6)	C10—C11—C12—C13	−0.5 (5)
C5—C4—C7—O1	−179.3 (3)	C11—C12—C13—O3	−179.7 (3)
C3—C4—C7—O1	−0.8 (4)	C11—C12—C13—C14	0.2 (5)
C5—C4—C7—C8	2.1 (4)	C16—O3—C13—C12	−1.1 (5)
C3—C4—C7—C8	−179.4 (3)	C16—O3—C13—C14	179.1 (3)
C9—O2—C8—C7	161.9 (3)	C12—C13—C14—C15	0.1 (5)
C9—O2—C8—S1	−76.7 (3)	O3—C13—C14—C15	179.9 (3)
O1—C7—C8—O2	19.8 (4)	C13—C14—C15—C10	0.0 (5)
C4—C7—C8—O2	−161.5 (2)	C11—C10—C15—C14	−0.3 (5)
O1—C7—C8—S1	−104.5 (3)	S1—C10—C15—C14	−177.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1i	0.98	2.54	3.406 (5)	147
C16—H16C···O1ii	0.96	2.47	3.421 (5)	170

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C8H8O1i	0.98	2.54	3.406(5)	147
C16H16CO1ii	0.96	2.47	3.421(5)	170

Symmetry codes: (i) ; (ii) .