2-(1,3-Benzoxazol-2-ylsulfan-yl)-1-phenyl-ethanone.

In the title compound, C(15)H(11)NO(2)S, a new thio-benzoxazole derivative, the dihedral angle between the benzoxazole ring and the phenyl ring is 9.91 (9)°. An inter-esting feature of the crystal structure is the short C⋯S [3.4858 (17) Å] contact, which is shorter than the sum of the van der Waals radii of these atoms. In the crystal structure, mol-ecules are linked together by zigzag inter-molecular C-H⋯N inter-actions into a column along the a axis. The crystal structure is further stabilized by inter-molecular π-π inter-actions [centroid-centroid = 3.8048 (10) Å].

Related literature

For applications of 2-(benzo[d]oxazol-2-ylthio)-1-phenyl­ethanone and β-keto-sulfones in organic synthesis, see: Marco et al. (1995 ▶); Fuju et al. (1988 ▶); Ni et al. (2006 ▶). For uses of haloalkyl sulfones, see: Grossert et al. (1984 ▶); Oishi et al. (1988 ▶); Antane et al. (2004 ▶). For their biological activity, see: Padmavathi et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H11NO2S

M = 269.31

Orthorhombic,

a = 4.8580 (2) Å

b = 14.0780 (5) Å

c = 18.6840 (7) Å

V = 1277.82 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.50 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.886, T max = 0.976

13902 measured reflections

3659 independent reflections

3175 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.093

S = 1.04

3659 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 1514 Friedel pairs

Flack parameter: 0.07 (7)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2004 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809033960/at2859sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033960/at2859Isup2.hkl

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

C15H11NO2S	Dx = 1.400 Mg m−3
Mr = 269.31	Melting point: 398 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4173 reflections
a = 4.8580 (2) Å	θ = 2.6–28.2°
b = 14.0780 (5) Å	µ = 0.25 mm−1
c = 18.6840 (7) Å	T = 296 K
V = 1277.82 (8) Å3	Needle, colourless
Z = 4	0.50 × 0.10 × 0.10 mm
F(000) = 560

Bruker SMART APEXII CCD area-detector diffractometer	3659 independent reflections
Radiation source: fine-focus sealed tube	3175 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 30.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→6
Tmin = 0.886, Tmax = 0.976	k = −19→19
13902 measured reflections	l = −26→26

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0487P)2 + 0.1389P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3659 reflections	Δρmax = 0.35 e Å−3
172 parameters	Δρmin = −0.19 e Å−3
0 restraints	Absolute structure: Flack (1983), 1514 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.07 (7)

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.01065 (10)	0.44145 (3)	0.66514 (2)	0.02920 (11)
O1	0.3102 (3)	0.29909 (9)	0.71157 (6)	0.0295 (3)
N1	0.4022 (3)	0.33643 (10)	0.59627 (7)	0.0250 (3)
C1	0.5079 (4)	0.23556 (11)	0.68726 (8)	0.0262 (3)
C2	0.6325 (4)	0.16254 (14)	0.72375 (10)	0.0346 (4)
H2A	0.5895	0.1480	0.7710	0.042*
C3	0.8271 (4)	0.11206 (14)	0.68500 (10)	0.0366 (4)
H3A	0.9193	0.0621	0.7071	0.044*
C4	0.8889 (4)	0.13370 (13)	0.61400 (10)	0.0341 (4)
H4A	1.0209	0.0980	0.5900	0.041*
C5	0.7576 (4)	0.20749 (13)	0.57839 (9)	0.0292 (4)
H5A	0.7982	0.2218	0.5310	0.035*
C6	0.5639 (3)	0.25876 (12)	0.61651 (8)	0.0244 (3)
C7	0.2612 (3)	0.35517 (12)	0.65300 (8)	0.0251 (3)
C8	−0.0098 (4)	0.47588 (12)	0.57236 (8)	0.0289 (3)
H8A	0.1664	0.5008	0.5567	0.035*
H8B	−0.0536	0.4209	0.5432	0.035*
C9	−0.2291 (3)	0.55059 (12)	0.56314 (9)	0.0266 (3)
C10	−0.2762 (4)	0.58747 (12)	0.48943 (9)	0.0264 (3)
C11	−0.4792 (4)	0.65637 (12)	0.47888 (10)	0.0337 (4)
H11A	−0.5823	0.6780	0.5175	0.040*
C12	−0.5275 (5)	0.69250 (13)	0.41129 (11)	0.0396 (5)
H12A	−0.6630	0.7383	0.4045	0.048*
C13	−0.3744 (4)	0.66049 (14)	0.35363 (11)	0.0397 (5)
H13A	−0.4070	0.6850	0.3082	0.048*
C14	−0.1733 (4)	0.59220 (15)	0.36330 (10)	0.0375 (4)
H14A	−0.0713	0.5707	0.3244	0.045*
C15	−0.1237 (4)	0.55572 (14)	0.43100 (10)	0.0312 (4)
H15A	0.0120	0.5099	0.4374	0.037*
O2	−0.3588 (3)	0.57915 (10)	0.61422 (7)	0.0390 (3)

	U11	U22	U33	U12	U13	U23
S1	0.0334 (2)	0.0325 (2)	0.02181 (18)	0.0053 (2)	0.00128 (18)	−0.00418 (15)
O1	0.0362 (7)	0.0345 (6)	0.0179 (5)	0.0024 (5)	0.0020 (5)	0.0012 (5)
N1	0.0279 (7)	0.0290 (7)	0.0180 (6)	0.0018 (6)	−0.0013 (5)	−0.0011 (5)
C1	0.0289 (8)	0.0297 (7)	0.0200 (6)	−0.0035 (8)	0.0007 (7)	0.0003 (5)
C2	0.0439 (11)	0.0348 (9)	0.0253 (8)	−0.0017 (8)	−0.0021 (8)	0.0072 (7)
C3	0.0413 (11)	0.0305 (9)	0.0381 (10)	0.0046 (8)	−0.0074 (8)	0.0052 (8)
C4	0.0343 (9)	0.0313 (9)	0.0367 (10)	0.0049 (8)	0.0024 (8)	−0.0049 (8)
C5	0.0322 (9)	0.0335 (9)	0.0219 (8)	−0.0007 (8)	0.0020 (7)	−0.0034 (7)
C6	0.0283 (9)	0.0263 (8)	0.0185 (7)	−0.0028 (6)	−0.0038 (6)	−0.0009 (6)
C7	0.0276 (8)	0.0279 (8)	0.0198 (7)	−0.0024 (7)	−0.0030 (6)	−0.0012 (6)
C8	0.0290 (8)	0.0332 (8)	0.0243 (7)	0.0037 (8)	0.0008 (8)	0.0017 (6)
C9	0.0253 (8)	0.0227 (7)	0.0316 (8)	−0.0029 (7)	0.0008 (6)	−0.0021 (7)
C10	0.0251 (8)	0.0221 (8)	0.0322 (9)	−0.0040 (6)	−0.0028 (7)	0.0011 (6)
C11	0.0319 (9)	0.0282 (8)	0.0409 (9)	0.0010 (8)	−0.0054 (8)	−0.0018 (7)
C12	0.0377 (11)	0.0300 (9)	0.0512 (11)	0.0011 (9)	−0.0159 (10)	0.0046 (8)
C13	0.0438 (11)	0.0370 (10)	0.0383 (10)	−0.0096 (9)	−0.0134 (8)	0.0083 (8)
C14	0.0359 (10)	0.0449 (11)	0.0317 (9)	−0.0048 (9)	−0.0024 (8)	0.0045 (8)
C15	0.0287 (8)	0.0335 (9)	0.0313 (8)	0.0005 (8)	−0.0023 (7)	0.0035 (8)
O2	0.0440 (8)	0.0376 (7)	0.0355 (7)	0.0095 (6)	0.0076 (6)	−0.0020 (6)

S1—C7	1.7343 (17)	C8—C9	1.507 (2)
S1—C8	1.8028 (16)	C8—H8A	0.9700
O1—C7	1.3704 (19)	C8—H8B	0.9700
O1—C1	1.389 (2)	C9—O2	1.212 (2)
N1—C7	1.290 (2)	C9—C10	1.489 (2)
N1—C6	1.398 (2)	C10—C15	1.393 (3)
C1—C2	1.374 (2)	C10—C11	1.397 (3)
C1—C6	1.389 (2)	C11—C12	1.381 (2)
C2—C3	1.387 (3)	C11—H11A	0.9300
C2—H2A	0.9300	C12—C13	1.385 (3)
C3—C4	1.394 (3)	C12—H12A	0.9300
C3—H3A	0.9300	C13—C14	1.383 (3)
C4—C5	1.389 (3)	C13—H13A	0.9300
C4—H4A	0.9300	C14—C15	1.386 (3)
C5—C6	1.383 (2)	C14—H14A	0.9300
C5—H5A	0.9300	C15—H15A	0.9300
C7—S1—C8	95.81 (8)	S1—C8—H8A	109.7
C7—O1—C1	103.29 (12)	C9—C8—H8B	109.7
C7—N1—C6	103.67 (14)	S1—C8—H8B	109.7
C2—C1—O1	128.62 (15)	H8A—C8—H8B	108.2
C2—C1—C6	124.18 (18)	O2—C9—C10	122.17 (16)
O1—C1—C6	107.20 (14)	O2—C9—C8	120.60 (16)
C1—C2—C3	115.13 (17)	C10—C9—C8	117.23 (14)
C1—C2—H2A	122.4	C15—C10—C11	119.18 (16)
C3—C2—H2A	122.4	C15—C10—C9	122.08 (16)
C2—C3—C4	122.13 (18)	C11—C10—C9	118.74 (16)
C2—C3—H3A	118.9	C12—C11—C10	120.30 (18)
C4—C3—H3A	118.9	C12—C11—H11A	119.8
C5—C4—C3	121.36 (18)	C10—C11—H11A	119.9
C5—C4—H4A	119.3	C11—C12—C13	120.01 (18)
C3—C4—H4A	119.3	C11—C12—H12A	120.0
C6—C5—C4	117.13 (16)	C13—C12—H12A	120.0
C6—C5—H5A	121.4	C14—C13—C12	120.29 (18)
C4—C5—H5A	121.4	C14—C13—H13A	119.9
C5—C6—C1	120.06 (16)	C12—C13—H13A	119.9
C5—C6—N1	130.61 (15)	C13—C14—C15	119.98 (19)
C1—C6—N1	109.33 (15)	C13—C14—H14A	120.0
N1—C7—O1	116.50 (15)	C15—C14—H14A	120.0
N1—C7—S1	128.59 (13)	C14—C15—C10	120.25 (17)
O1—C7—S1	114.90 (11)	C14—C15—H15A	119.9
C9—C8—S1	109.67 (12)	C10—C15—H15A	119.9
C9—C8—H8A	109.7
C7—O1—C1—C2	−179.71 (19)	C1—O1—C7—S1	178.11 (12)
C7—O1—C1—C6	0.52 (17)	C8—S1—C7—N1	8.41 (18)
O1—C1—C2—C3	−178.94 (17)	C8—S1—C7—O1	−170.44 (13)
C6—C1—C2—C3	0.8 (3)	C7—S1—C8—C9	177.42 (12)
C1—C2—C3—C4	−0.5 (3)	S1—C8—C9—O2	0.7 (2)
C2—C3—C4—C5	0.0 (3)	S1—C8—C9—C10	−179.75 (13)
C3—C4—C5—C6	0.3 (3)	O2—C9—C10—C15	178.88 (17)
C4—C5—C6—C1	0.0 (2)	C8—C9—C10—C15	−0.7 (2)
C4—C5—C6—N1	179.14 (16)	O2—C9—C10—C11	−0.8 (3)
C2—C1—C6—C5	−0.5 (3)	C8—C9—C10—C11	179.60 (16)
O1—C1—C6—C5	179.26 (15)	C15—C10—C11—C12	0.0 (3)
C2—C1—C6—N1	−179.86 (17)	C9—C10—C11—C12	179.69 (17)
O1—C1—C6—N1	−0.08 (18)	C10—C11—C12—C13	0.0 (3)
C7—N1—C6—C5	−179.68 (17)	C11—C12—C13—C14	0.2 (3)
C7—N1—C6—C1	−0.43 (18)	C12—C13—C14—C15	−0.2 (3)
C6—N1—C7—O1	0.83 (19)	C13—C14—C15—C10	0.1 (3)
C6—N1—C7—S1	−178.00 (13)	C11—C10—C15—C14	0.0 (3)
C1—O1—C7—N1	−0.89 (19)	C9—C10—C15—C14	−179.73 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···N1i	0.93	2.56	3.395 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯N1i	0.93	2.56	3.395 (2)	149

Symmetry code: (i) .