(R)-2-Phen-oxy-1-(4-phenyl-2-sulfan-ylidene-1,3-oxazolidin-3-yl)ethanone.

The central 1,3-oxazolidine-2-thione ring in the title compound, C(17)H(15)NO(3)S, is approximately planar with maximum deviations of 0.036 (4) and -0.041 (5) Å for the O and methyl-ene-C atoms, respectively. The dihedral angles formed between this plane and the two benzene rings, which lie to the same side of the central plane, are 86.5 (2) [ring-bound benzene] and 50.6 (3)°. The ethan-1-one residue is also twisted out of the central plane, forming a O-C-N-C torsion angle of 151.5 (5)°. The dihedral angle formed by the benzene rings is 62.8 (2)° so that overall, the mol-ecule has a twisted U-shape. In the crystal, mol-ecules are linked into supra-molecular arrays two mol-ecules thick in the bc plane through C-H⋯O, C-H⋯S and C-H⋯π inter-actions.

Related literature

For background to oxazolidine-2-thio­nes, see: Evans et al. (1981 ▶); Crimmins & King (1998 ▶); Zhang et al. (2004) ▶; Shinisha & Sunoj (2010 ▶); Tamura et al. (2009 ▶). For related structures, see: Kitoh et al. (2002 ▶). For the synthesis, see: Wu et al. (2004 ▶); Rodrigues et al. (2005 ▶).

Experimental

Crystal data

C17H15NO3S

M = 313.37

Monoclinic,

a = 33.514 (3) Å

b = 5.7514 (6) Å

c = 7.7172 (8) Å

β = 93.808 (7)°

V = 1484.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 126 K

0.30 × 0.25 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

7408 measured reflections

2588 independent reflections

2166 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.180

S = 1.08

2588 reflections

199 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.81 e Å−3

Δρmin = −0.47 e Å−3

Absolute structure: Flack (1983 ▶), 1143 Friedel pairs

Flack parameter: 0.01 (18)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); 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: MarvinSketch (Chemaxon, 2010 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681103858X/hg5095sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103858X/hg5095Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681103858X/hg5095Isup3.cml

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

C17H15NO3S	F(000) = 656
Mr = 313.37	Dx = 1.402 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 2062 reflections
a = 33.514 (3) Å	θ = 2.7–26.4°
b = 5.7514 (6) Å	µ = 0.23 mm−1
c = 7.7172 (8) Å	T = 126 K
β = 93.808 (7)°	Block, colourless
V = 1484.2 (3) Å3	0.30 × 0.25 × 0.16 mm
Z = 4

Bruker APEXII CCD diffractometer	2166 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.064
graphite	θmax = 25.0°, θmin = 2.7°
φ and ω scans	h = −39→36
7408 measured reflections	k = −6→6
2588 independent reflections	l = −8→9

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066	H-atom parameters constrained
wR(F2) = 0.180	w = 1/[σ2(Fo2) + (0.1039P)2 + 1.9443P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2588 reflections	Δρmax = 0.81 e Å−3
199 parameters	Δρmin = −0.47 e Å−3
1 restraint	Absolute structure: Flack (1983), 1143 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (18)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.71650 (13)	0.0824 (8)	0.6314 (6)	0.0265 (11)
C2	0.70382 (14)	0.0160 (10)	0.3371 (6)	0.0298 (11)
H2A	0.6857	−0.1125	0.2984	0.036*
H2B	0.7219	0.0499	0.2439	0.036*
C3	0.67974 (14)	0.2332 (8)	0.3797 (6)	0.0248 (10)
H3	0.6906	0.3717	0.3202	0.030*
C4	0.63525 (14)	0.2206 (8)	0.3422 (6)	0.0240 (10)
C5	0.61306 (13)	0.0403 (10)	0.4132 (6)	0.0284 (10)
H5	0.6263	−0.0765	0.4823	0.034*
C6	0.57230 (14)	0.0333 (10)	0.3826 (6)	0.0311 (10)
H6	0.5574	−0.0873	0.4323	0.037*
C7	0.55245 (14)	0.2019 (10)	0.2792 (7)	0.0332 (12)
H7	0.5243	0.1948	0.2564	0.040*
C8	0.57425 (15)	0.3789 (9)	0.2104 (7)	0.0311 (11)
H8	0.5609	0.4950	0.1409	0.037*
C9	0.61494 (15)	0.3893 (8)	0.2410 (6)	0.0274 (11)
H9	0.6295	0.5126	0.1928	0.033*
C10	0.67735 (13)	0.4532 (9)	0.6533 (7)	0.0272 (11)
C11	0.67426 (15)	0.4547 (9)	0.8496 (7)	0.0318 (12)
H11A	0.6608	0.3109	0.8856	0.038*
H11B	0.7014	0.4586	0.9086	0.038*
C12	0.61226 (14)	0.6591 (8)	0.8538 (6)	0.0242 (10)
C13	0.59105 (15)	0.4913 (9)	0.7557 (6)	0.0310 (12)
H13	0.6045	0.3586	0.7149	0.037*
C14	0.55026 (14)	0.5183 (10)	0.7176 (6)	0.0319 (11)
H14	0.5360	0.4038	0.6498	0.038*
C15	0.52995 (15)	0.7094 (10)	0.7768 (7)	0.0343 (12)
H15	0.5019	0.7247	0.7525	0.041*
C16	0.55166 (17)	0.8801 (10)	0.8735 (7)	0.0358 (12)
H16	0.5382	1.0130	0.9138	0.043*
C17	0.59217 (15)	0.8566 (9)	0.9103 (6)	0.0291 (11)
H17	0.6066	0.9742	0.9741	0.035*
N	0.68964 (11)	0.2510 (7)	0.5738 (5)	0.0255 (9)
O1	0.72682 (10)	−0.0467 (6)	0.4973 (4)	0.0305 (8)
O2	0.66648 (10)	0.6161 (6)	0.5650 (4)	0.0300 (8)
O3	0.65227 (10)	0.6512 (6)	0.8994 (4)	0.0306 (8)
S	0.73540 (4)	0.0379 (2)	0.82903 (16)	0.0340 (4)

	U11	U22	U33	U12	U13	U23
C1	0.023 (2)	0.030 (3)	0.026 (3)	0.0007 (18)	0.0016 (18)	0.001 (2)
C2	0.035 (2)	0.034 (3)	0.021 (2)	0.003 (2)	−0.0009 (18)	0.000 (2)
C3	0.037 (3)	0.025 (2)	0.012 (2)	0.004 (2)	0.0019 (18)	0.0023 (19)
C4	0.035 (3)	0.023 (2)	0.014 (2)	0.0003 (19)	0.0044 (18)	−0.0011 (19)
C5	0.035 (2)	0.026 (2)	0.024 (2)	−0.002 (2)	−0.0004 (18)	0.001 (2)
C6	0.037 (3)	0.028 (2)	0.029 (3)	−0.003 (2)	0.0054 (19)	−0.002 (3)
C7	0.023 (2)	0.049 (3)	0.027 (3)	0.000 (2)	−0.002 (2)	−0.006 (2)
C8	0.037 (3)	0.035 (3)	0.021 (3)	0.003 (2)	−0.001 (2)	−0.005 (2)
C9	0.039 (3)	0.025 (3)	0.019 (3)	0.002 (2)	0.004 (2)	−0.002 (2)
C10	0.021 (2)	0.027 (2)	0.034 (3)	−0.0025 (18)	−0.001 (2)	0.000 (2)
C11	0.032 (3)	0.033 (3)	0.030 (3)	0.002 (2)	−0.001 (2)	0.001 (2)
C12	0.029 (2)	0.024 (2)	0.020 (2)	−0.0033 (18)	0.0030 (18)	−0.001 (2)
C13	0.036 (3)	0.032 (3)	0.026 (3)	−0.004 (2)	0.011 (2)	−0.006 (2)
C14	0.033 (3)	0.038 (3)	0.024 (2)	−0.004 (2)	0.0004 (18)	−0.003 (2)
C15	0.031 (3)	0.039 (3)	0.033 (3)	0.004 (2)	0.000 (2)	0.004 (2)
C16	0.045 (3)	0.034 (3)	0.029 (3)	0.009 (2)	0.006 (2)	0.001 (2)
C17	0.040 (3)	0.027 (3)	0.020 (3)	0.000 (2)	0.003 (2)	0.000 (2)
N	0.026 (2)	0.031 (2)	0.019 (2)	0.0027 (17)	−0.0002 (15)	−0.0011 (18)
O1	0.0286 (18)	0.0299 (19)	0.032 (2)	0.0042 (13)	−0.0022 (14)	0.0018 (15)
O2	0.0333 (19)	0.029 (2)	0.0276 (19)	0.0021 (14)	0.0027 (14)	0.0049 (16)
O3	0.036 (2)	0.0321 (18)	0.0238 (18)	0.0025 (14)	0.0029 (14)	−0.0057 (15)
S	0.0338 (6)	0.0398 (7)	0.0275 (7)	0.0061 (6)	−0.0047 (4)	0.0051 (6)

C1—O1	1.338 (6)	C9—H9	0.9500
C1—N	1.377 (6)	C10—O2	1.201 (6)
C1—S	1.632 (5)	C10—N	1.390 (6)
C2—O1	1.458 (5)	C10—C11	1.525 (7)
C2—C3	1.535 (7)	C11—O3	1.416 (6)
C2—H2A	0.9900	C11—H11A	0.9900
C2—H2B	0.9900	C11—H11B	0.9900
C3—C4	1.501 (6)	C12—O3	1.364 (6)
C3—N	1.516 (6)	C12—C13	1.392 (7)
C3—H3	1.0000	C12—C17	1.404 (7)
C4—C9	1.394 (7)	C13—C14	1.388 (7)
C4—C5	1.408 (7)	C13—H13	0.9500
C5—C6	1.371 (6)	C14—C15	1.386 (8)
C5—H5	0.9500	C14—H14	0.9500
C6—C7	1.396 (7)	C15—C16	1.407 (8)
C6—H6	0.9500	C15—H15	0.9500
C7—C8	1.379 (8)	C16—C17	1.375 (7)
C7—H7	0.9500	C16—H16	0.9500
C8—C9	1.370 (7)	C17—H17	0.9500
C8—H8	0.9500
O1—C1—N	109.7 (4)	O2—C10—N	119.3 (4)
O1—C1—S	122.1 (3)	O2—C10—C11	121.4 (4)
N—C1—S	128.1 (4)	N—C10—C11	119.0 (4)
O1—C2—C3	106.0 (4)	O3—C11—C10	110.2 (4)
O1—C2—H2A	110.5	O3—C11—H11A	109.6
C3—C2—H2A	110.5	C10—C11—H11A	109.6
O1—C2—H2B	110.5	O3—C11—H11B	109.6
C3—C2—H2B	110.5	C10—C11—H11B	109.6
H2A—C2—H2B	108.7	H11A—C11—H11B	108.1
C4—C3—N	110.1 (4)	O3—C12—C13	125.1 (4)
C4—C3—C2	116.7 (4)	O3—C12—C17	115.5 (4)
N—C3—C2	100.5 (3)	C13—C12—C17	119.4 (4)
C4—C3—H3	109.7	C14—C13—C12	119.8 (5)
N—C3—H3	109.7	C14—C13—H13	120.1
C2—C3—H3	109.7	C12—C13—H13	120.1
C9—C4—C5	118.6 (4)	C15—C14—C13	121.2 (5)
C9—C4—C3	121.0 (4)	C15—C14—H14	119.4
C5—C4—C3	120.3 (4)	C13—C14—H14	119.4
C6—C5—C4	120.0 (5)	C14—C15—C16	118.7 (5)
C6—C5—H5	120.0	C14—C15—H15	120.6
C4—C5—H5	120.0	C16—C15—H15	120.6
C5—C6—C7	120.6 (5)	C17—C16—C15	120.6 (5)
C5—C6—H6	119.7	C17—C16—H16	119.7
C7—C6—H6	119.7	C15—C16—H16	119.7
C8—C7—C6	119.2 (4)	C16—C17—C12	120.2 (5)
C8—C7—H7	120.4	C16—C17—H17	119.9
C6—C7—H7	120.4	C12—C17—H17	119.9
C9—C8—C7	120.8 (5)	C1—N—C10	130.8 (4)
C9—C8—H8	119.6	C1—N—C3	111.6 (4)
C7—C8—H8	119.6	C10—N—C3	116.2 (4)
C8—C9—C4	120.7 (5)	C1—O1—C2	111.7 (3)
C8—C9—H9	119.7	C12—O3—C11	118.5 (4)
C4—C9—H9	119.7
O1—C2—C3—C4	−124.8 (4)	C15—C16—C17—C12	−1.0 (8)
O1—C2—C3—N	−5.8 (5)	O3—C12—C17—C16	−179.0 (5)
N—C3—C4—C9	119.5 (5)	C13—C12—C17—C16	2.0 (7)
C2—C3—C4—C9	−126.8 (5)	O1—C1—N—C10	−163.8 (4)
N—C3—C4—C5	−58.7 (6)	S—C1—N—C10	14.6 (7)
C2—C3—C4—C5	54.9 (6)	O1—C1—N—C3	1.3 (5)
C9—C4—C5—C6	−0.1 (7)	S—C1—N—C3	179.7 (4)
C3—C4—C5—C6	178.1 (4)	O2—C10—N—C1	151.5 (5)
C4—C5—C6—C7	1.0 (7)	C11—C10—N—C1	−34.2 (7)
C5—C6—C7—C8	−1.2 (7)	O2—C10—N—C3	−13.1 (6)
C6—C7—C8—C9	0.7 (7)	C11—C10—N—C3	161.2 (4)
C7—C8—C9—C4	0.1 (7)	C4—C3—N—C1	126.7 (4)
C5—C4—C9—C8	−0.4 (7)	C2—C3—N—C1	3.0 (5)
C3—C4—C9—C8	−178.7 (4)	C4—C3—N—C10	−65.8 (5)
O2—C10—C11—O3	8.6 (6)	C2—C3—N—C10	170.5 (4)
N—C10—C11—O3	−165.6 (4)	N—C1—O1—C2	−5.5 (5)
O3—C12—C13—C14	179.9 (4)	S—C1—O1—C2	175.9 (4)
C17—C12—C13—C14	−1.2 (7)	C3—C2—O1—C1	7.3 (5)
C12—C13—C14—C15	−0.5 (8)	C13—C12—O3—C11	−2.3 (7)
C13—C14—C15—C16	1.5 (8)	C17—C12—O3—C11	178.8 (4)
C14—C15—C16—C17	−0.7 (8)	C10—C11—O3—C12	69.4 (5)

Cg1 and Cg2 are the centroids of the C4–C9 and C12–C17 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.95	2.29	3.202 (6)	162
C9—H9···O3ii	0.95	2.56	3.350 (6)	140
C11—H11b···Siii	0.99	2.87	3.814 (5)	160
C17—H17···Cg1iv	0.95	2.99	3.703 (5)	133
C8—H8···Cg2ii	0.95	2.79	3.523 (6)	135

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C4–C9 and C12–C17 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.95	2.29	3.202 (6)	162
C9—H9⋯O3ii	0.95	2.56	3.350 (6)	140
C11—H11b⋯Siii	0.99	2.87	3.814 (5)	160
C17—H17⋯Cg1iv	0.95	2.99	3.703 (5)	133
C8—H8⋯Cg2ii	0.95	2.79	3.523 (6)	135

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