S-Phenyl 4-meth-oxy-benzothio-ate.

In the mol-ecule of the title thio-ester, C(14)H(12)O(2)S, the dihedral angle between the phenyl and benzene rings is 71.8 (3)°. The meth-oxy group is essentially coplanar with the benezene ring to which it is bonded, with an r.m.s. deviation of 0.0065 (5) Å for the non-H atoms involved. In the crystal, weak C-H⋯π inter-actions are present.

Related literature

For background to and applications of thio­esters, see: Agapiou & Krische (2003 ▶); Choi et al. (2003 ▶); El-Azab & Abdel-Aziz (2012 ▶); Horst et al. (2007 ▶); Howell et al. (2006 ▶); Jew et al. (2003 ▶); Liebeskind & Srogl (2000 ▶); McGarvey et al. (1986 ▶); Ozaki et al. (2003 ▶); Shah et al. (2002 ▶); Yang & Drueckhammer (2001 ▶). For related structures and the synthesis of similar compounds, see: Barbero et al. (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H12O2S

M = 244.31

Orthorhombic,

a = 5.4478 (2) Å

b = 8.2149 (3) Å

c = 27.3841 (6) Å

V = 1225.52 (7) Å3

Z = 4

Cu Kα radiation

μ = 2.23 mm−1

T = 296 K

0.58 × 0.22 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.357, T max = 0.699

7810 measured reflections

2144 independent reflections

1479 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.199

S = 1.22

2144 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.28 e Å−3

Absolute structure: Flack (1983 ▶), 1811 Friedel pairs

Flack parameter: 0.07 (5)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005454/lh5413sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005454/lh5413Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005454/lh5413Isup3.cml

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

C14H12O2S	Dx = 1.324 Mg m−3
Mr = 244.31	Melting point = 366–367 K
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2144 reflections
a = 5.4478 (2) Å	θ = 3.2–69.4°
b = 8.2149 (3) Å	µ = 2.23 mm−1
c = 27.3841 (6) Å	T = 296 K
V = 1225.52 (7) Å3	Needle, colourless
Z = 4	0.58 × 0.22 × 0.17 mm
F(000) = 512

Bruker SMART APEXII CCD area-detector diffractometer	2144 independent reflections
Radiation source: fine-focus sealed tube	1479 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
φ and ω scans	θmax = 69.4°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −4→6
Tmin = 0.357, Tmax = 0.699	k = −9→8
7810 measured reflections	l = −32→29

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.056	w = 1/[σ2(Fo2) + (0.0897P)2 + 0.2372P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.199	(Δ/σ)max = 0.001
S = 1.22	Δρmax = 0.32 e Å−3
2144 reflections	Δρmin = −0.28 e Å−3
156 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.025 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 1811 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.07 (5)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.2447 (3)	0.2241 (2)	0.88540 (4)	0.0866 (6)
O1	−0.1014 (8)	0.0079 (5)	0.87109 (10)	0.0848 (13)
O2	−0.0150 (7)	−0.0916 (5)	1.10026 (10)	0.0712 (10)
C1	0.0101 (8)	0.0386 (6)	0.95439 (14)	0.0579 (11)
C2	−0.1770 (8)	−0.0607 (6)	0.97065 (16)	0.0641 (12)
H2A	−0.2939	−0.0981	0.9486	0.077*
C3	−0.1940 (8)	−0.1055 (7)	1.01918 (14)	0.0657 (13)
H3A	−0.3225	−0.1713	1.0297	0.079*
C4	−0.0204 (8)	−0.0527 (6)	1.05180 (14)	0.0596 (11)
C5	0.1682 (8)	0.0475 (6)	1.03636 (15)	0.0637 (12)
H5A	0.2841	0.0853	1.0585	0.076*
C6	0.1830 (8)	0.0911 (7)	0.98763 (15)	0.0625 (12)
H6A	0.3117	0.1568	0.9771	0.075*
C7	0.0229 (9)	0.0742 (7)	0.90125 (15)	0.0653 (13)
C8	0.2346 (9)	0.2180 (7)	0.82059 (16)	0.0684 (13)
C9	0.4109 (10)	0.1329 (7)	0.79629 (16)	0.0773 (15)
H9A	0.5299	0.0757	0.8136	0.093*
C10	0.4122 (11)	0.1319 (8)	0.74530 (17)	0.0827 (17)
H10A	0.5297	0.0722	0.7284	0.099*
C11	0.2390 (10)	0.2194 (7)	0.72047 (17)	0.0779 (14)
H11A	0.2402	0.2198	0.6865	0.094*
C12	0.0654 (11)	0.3056 (9)	0.74480 (18)	0.0860 (18)
H12A	−0.0511	0.3651	0.7275	0.103*
C13	0.0619 (11)	0.3049 (8)	0.79550 (19)	0.0818 (16)
H13A	−0.0574	0.3634	0.8123	0.098*
C14	−0.2089 (11)	−0.1900 (9)	1.11832 (18)	0.096 (2)
H14A	−0.1840	−0.2103	1.1525	0.144*
H14B	−0.2115	−0.2915	1.1010	0.144*
H14C	−0.3624	−0.1347	1.1137	0.144*

	U11	U22	U33	U12	U13	U23
S1	0.1088 (11)	0.0977 (13)	0.0532 (6)	−0.0329 (9)	−0.0016 (6)	−0.0022 (6)
O1	0.088 (3)	0.107 (4)	0.0589 (17)	−0.019 (2)	−0.0185 (16)	0.0018 (19)
O2	0.083 (2)	0.079 (3)	0.0521 (16)	−0.0038 (17)	−0.0032 (13)	0.0042 (16)
C1	0.058 (2)	0.064 (3)	0.052 (2)	0.0023 (19)	−0.0063 (17)	−0.011 (2)
C2	0.061 (3)	0.066 (4)	0.065 (2)	−0.006 (2)	−0.0035 (18)	0.001 (2)
C3	0.061 (3)	0.083 (4)	0.053 (2)	−0.013 (2)	−0.0014 (17)	0.003 (2)
C4	0.066 (3)	0.060 (3)	0.053 (2)	−0.001 (2)	−0.0001 (17)	−0.006 (2)
C5	0.066 (3)	0.069 (4)	0.056 (2)	−0.008 (2)	−0.0074 (17)	0.000 (2)
C6	0.061 (3)	0.066 (4)	0.060 (2)	−0.009 (2)	−0.0048 (18)	−0.001 (2)
C7	0.066 (3)	0.077 (4)	0.053 (2)	0.008 (2)	−0.0078 (18)	−0.012 (2)
C8	0.069 (3)	0.077 (4)	0.058 (2)	−0.008 (3)	−0.0016 (19)	0.005 (2)
C9	0.077 (3)	0.087 (4)	0.068 (3)	0.001 (3)	−0.003 (2)	0.013 (3)
C10	0.080 (3)	0.102 (5)	0.067 (3)	0.004 (3)	0.007 (2)	0.004 (3)
C11	0.085 (3)	0.096 (4)	0.053 (2)	−0.005 (3)	−0.005 (2)	0.011 (2)
C12	0.081 (4)	0.108 (5)	0.069 (3)	0.006 (3)	−0.015 (3)	0.013 (3)
C13	0.080 (3)	0.086 (5)	0.080 (3)	0.007 (3)	0.002 (2)	0.000 (3)
C14	0.103 (4)	0.120 (6)	0.065 (3)	−0.033 (4)	0.004 (3)	0.014 (3)

S1—C8	1.776 (4)	C6—H6A	0.9300
S1—C7	1.779 (6)	C8—C9	1.362 (7)
O1—C7	1.199 (5)	C8—C13	1.366 (7)
O2—C4	1.366 (5)	C9—C10	1.397 (6)
O2—C14	1.419 (6)	C9—H9A	0.9300
C1—C6	1.379 (6)	C10—C11	1.367 (7)
C1—C2	1.380 (6)	C10—H10A	0.9300
C1—C7	1.486 (6)	C11—C12	1.356 (8)
C2—C3	1.382 (6)	C11—H11A	0.9300
C2—H2A	0.9300	C12—C13	1.389 (7)
C3—C4	1.371 (6)	C12—H12A	0.9300
C3—H3A	0.9300	C13—H13A	0.9300
C4—C5	1.383 (6)	C14—H14A	0.9600
C5—C6	1.384 (6)	C14—H14B	0.9600
C5—H5A	0.9300	C14—H14C	0.9600
C8—S1—C7	101.7 (2)	C9—C8—S1	118.7 (4)
C4—O2—C14	117.1 (4)	C13—C8—S1	120.6 (4)
C6—C1—C2	118.5 (4)	C8—C9—C10	119.7 (5)
C6—C1—C7	123.6 (4)	C8—C9—H9A	120.2
C2—C1—C7	117.8 (4)	C10—C9—H9A	120.2
C1—C2—C3	121.1 (4)	C11—C10—C9	119.4 (5)
C1—C2—H2A	119.4	C11—C10—H10A	120.3
C3—C2—H2A	119.4	C9—C10—H10A	120.3
C4—C3—C2	119.7 (4)	C12—C11—C10	120.7 (4)
C4—C3—H3A	120.1	C12—C11—H11A	119.6
C2—C3—H3A	120.1	C10—C11—H11A	119.6
O2—C4—C3	125.0 (4)	C11—C12—C13	119.9 (5)
O2—C4—C5	114.9 (4)	C11—C12—H12A	120.0
C3—C4—C5	120.1 (4)	C13—C12—H12A	120.0
C4—C5—C6	119.5 (4)	C8—C13—C12	119.7 (5)
C4—C5—H5A	120.3	C8—C13—H13A	120.2
C6—C5—H5A	120.3	C12—C13—H13A	120.2
C1—C6—C5	121.0 (4)	O2—C14—H14A	109.5
C1—C6—H6A	119.5	O2—C14—H14B	109.5
C5—C6—H6A	119.5	H14A—C14—H14B	109.5
O1—C7—C1	124.0 (5)	O2—C14—H14C	109.5
O1—C7—S1	122.0 (4)	H14A—C14—H14C	109.5
C1—C7—S1	114.0 (3)	H14B—C14—H14C	109.5
C9—C8—C13	120.5 (5)
C6—C1—C2—C3	0.8 (7)	C6—C1—C7—S1	−12.0 (6)
C7—C1—C2—C3	176.9 (5)	C2—C1—C7—S1	172.1 (3)
C1—C2—C3—C4	−0.9 (8)	C8—S1—C7—O1	−5.6 (5)
C14—O2—C4—C3	−2.2 (8)	C8—S1—C7—C1	173.6 (4)
C14—O2—C4—C5	178.1 (5)	C7—S1—C8—C9	−99.8 (5)
C2—C3—C4—O2	−178.6 (5)	C7—S1—C8—C13	84.1 (5)
C2—C3—C4—C5	1.2 (8)	C13—C8—C9—C10	−1.3 (8)
O2—C4—C5—C6	178.4 (5)	S1—C8—C9—C10	−177.4 (5)
C3—C4—C5—C6	−1.3 (8)	C8—C9—C10—C11	1.4 (9)
C2—C1—C6—C5	−0.9 (8)	C9—C10—C11—C12	−0.6 (9)
C7—C1—C6—C5	−176.8 (5)	C10—C11—C12—C13	−0.3 (9)
C4—C5—C6—C1	1.2 (7)	C9—C8—C13—C12	0.4 (9)
C6—C1—C7—O1	167.1 (5)	S1—C8—C13—C12	176.5 (5)
C2—C1—C7—O1	−8.8 (8)	C11—C12—C13—C8	0.4 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Cg1i	0.93	2.96	3.658 (6)	133

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯Cg1i	0.93	2.96	3.658 (6)	133

Symmetry code: (i) .