3-[2-(1H-Benzimidazol-2-ylsulfan-yl)eth-yl]-1,3-oxazolidin-2-one.

In the title compound, C(12)H(13)N(3)O(2)S, the oxazolidin ring displays an envelope conformation. The dihedral angle between the benzimidazole ring and the 1,3-oxazolidin-2-one mean plane is 69.85 (13)°. In the crystal, mol-ecules are linked by inter-molecular N-H⋯N hydrogen bonds, forming a chain parallel to the b axis.

Related literature

For the structures of oxazolidin-2-one linked to dioxoindolin, quinoxaline, benzodiazepin-2(3H)-one and indolo[2,3-b]quinoxalin, see: Al Subari et al. (2010a ▶,b ▶); Ahoya et al. (2010 ▶); Ballo et al. (2010 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C12H13N3O2S

M = 263.31

Orthorhombic,

a = 8.258 (1) Å

b = 10.074 (1) Å

c = 29.201 (3) Å

V = 2429.3 (5) Å3

Z = 8

Cu Kα radiation

μ = 2.37 mm−1

T = 296 K

0.25 × 0.10 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.589, T max = 0.891

2065 measured reflections

2065 independent reflections

1580 reflections with I > 2σ(I)

2 standard reflections every 90 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.138

S = 1.04

2065 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810045897/dn2620sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045897/dn2620Isup2.hkl

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

C12H13N3O2S	F(000) = 1104
Mr = 263.31	Dx = 1.440 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 8.258 (1) Å	θ = 25–35°
b = 10.074 (1) Å	µ = 2.37 mm−1
c = 29.201 (3) Å	T = 296 K
V = 2429.3 (5) Å3	Plate, colourless
Z = 8	0.25 × 0.10 × 0.05 mm

Enraf–Nonius CAD-4 diffractometer	1580 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.0000
graphite	θmax = 64.9°, θmin = 3.0°
ω–2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = 0→11
Tmin = 0.589, Tmax = 0.891	l = 0→34
2065 measured reflections	2 standard reflections every 90 min
2065 independent reflections	intensity decay: none

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.138	w = 1/[σ2(Fo2) + (0.0753P)2 + 1.285P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2065 reflections	Δρmax = 0.50 e Å−3
164 parameters	Δρmin = −0.26 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0023 (3)

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.

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 > σ(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	0.4252 (3)	0.6613 (3)	0.32287 (8)	0.0308 (6)
C2	0.5563 (4)	0.7150 (3)	0.29974 (10)	0.0418 (7)
H2	0.5765	0.8058	0.2996	0.050*
C3	0.6553 (4)	0.6266 (3)	0.27685 (11)	0.0491 (8)
H3	0.7451	0.6589	0.2612	0.059*
C4	0.6247 (4)	0.4910 (3)	0.27658 (10)	0.0452 (8)
H4	0.6930	0.4349	0.2602	0.054*
C5	0.4960 (4)	0.4382 (3)	0.29994 (10)	0.0387 (7)
H5	0.4772	0.3471	0.3000	0.046*
C6	0.3939 (3)	0.5243 (3)	0.32364 (8)	0.0300 (6)
N7	0.2541 (3)	0.4990 (2)	0.34878 (7)	0.0331 (5)
C8	0.2044 (3)	0.6179 (3)	0.36218 (9)	0.0323 (6)
N9	0.3018 (3)	0.7182 (2)	0.34785 (7)	0.0341 (5)
H9	0.2890	0.8014	0.3533	0.041*
S10	0.03324 (10)	0.65185 (8)	0.39498 (3)	0.0466 (3)
C11	−0.0806 (4)	0.5004 (3)	0.38524 (11)	0.0461 (8)
H11A	−0.0786	0.4786	0.3529	0.055*
H11B	−0.0306	0.4279	0.4019	0.055*
C12	−0.2545 (4)	0.5167 (4)	0.40086 (11)	0.0515 (8)
H12A	−0.3071	0.5824	0.3817	0.062*
H12B	−0.3109	0.4331	0.3967	0.062*
N13	−0.2688 (3)	0.5569 (3)	0.44810 (8)	0.0421 (6)
C14	−0.2251 (4)	0.4720 (4)	0.48622 (11)	0.0524 (9)
H14A	−0.1101	0.4527	0.4866	0.063*
H14B	−0.2857	0.3895	0.4859	0.063*
C15	−0.2743 (4)	0.5603 (4)	0.52586 (12)	0.0624 (10)
H15A	−0.3162	0.5079	0.5511	0.075*
H15B	−0.1832	0.6124	0.5366	0.075*
O16	−0.3993 (3)	0.6452 (2)	0.50692 (8)	0.0568 (6)
C17	−0.3857 (4)	0.6431 (3)	0.46087 (11)	0.0465 (8)
O18	−0.4713 (3)	0.7117 (3)	0.43673 (9)	0.0683 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0367 (14)	0.0282 (15)	0.0275 (12)	0.0002 (11)	−0.0008 (11)	0.0017 (10)
C2	0.0495 (18)	0.0290 (15)	0.0469 (17)	−0.0053 (13)	0.0046 (14)	0.0035 (12)
C3	0.0486 (18)	0.0473 (18)	0.0513 (18)	−0.0047 (16)	0.0098 (15)	0.0036 (15)
C4	0.0474 (17)	0.0447 (18)	0.0436 (17)	0.0103 (15)	0.0090 (13)	−0.0055 (13)
C5	0.0432 (16)	0.0254 (14)	0.0474 (16)	0.0052 (13)	0.0044 (13)	−0.0010 (12)
C6	0.0351 (14)	0.0218 (13)	0.0330 (13)	0.0008 (11)	−0.0046 (11)	0.0008 (10)
N7	0.0381 (12)	0.0221 (12)	0.0391 (12)	0.0007 (9)	0.0051 (10)	0.0001 (9)
C8	0.0376 (15)	0.0227 (13)	0.0365 (14)	0.0019 (11)	0.0012 (11)	−0.0006 (11)
N9	0.0406 (13)	0.0176 (11)	0.0441 (13)	−0.0002 (10)	0.0036 (10)	−0.0018 (9)
S10	0.0457 (5)	0.0336 (4)	0.0604 (5)	−0.0002 (3)	0.0160 (3)	−0.0094 (3)
C11	0.0460 (17)	0.0395 (18)	0.0527 (18)	−0.0037 (14)	0.0117 (15)	−0.0059 (13)
C12	0.0413 (16)	0.061 (2)	0.0521 (18)	−0.0089 (16)	0.0026 (15)	−0.0091 (16)
N13	0.0346 (13)	0.0480 (15)	0.0437 (13)	0.0020 (12)	0.0031 (11)	0.0000 (11)
C14	0.0382 (17)	0.059 (2)	0.060 (2)	0.0090 (16)	0.0014 (15)	0.0143 (17)
C15	0.047 (2)	0.088 (3)	0.053 (2)	−0.003 (2)	−0.0054 (15)	0.0077 (19)
O16	0.0518 (14)	0.0638 (17)	0.0549 (13)	0.0065 (12)	0.0019 (11)	−0.0115 (11)
C17	0.0414 (17)	0.0403 (17)	0.0578 (19)	−0.0041 (15)	0.0020 (15)	−0.0040 (15)
O18	0.0727 (17)	0.0523 (16)	0.0798 (18)	0.0179 (14)	−0.0127 (14)	0.0047 (13)

S10—C8	1.741 (3)	C4—C5	1.370 (4)
S10—C11	1.815 (3)	C5—C6	1.394 (4)
O16—C15	1.450 (4)	C11—C12	1.516 (5)
O16—C17	1.350 (4)	C14—C15	1.515 (5)
O18—C17	1.214 (4)	C2—H2	0.9298
N7—C6	1.392 (3)	C3—H3	0.9299
N7—C8	1.325 (4)	C4—H4	0.9308
N9—C1	1.378 (3)	C5—H5	0.9308
N9—C8	1.358 (4)	C11—H11A	0.9697
N13—C12	1.443 (4)	C11—H11B	0.9698
N13—C14	1.449 (4)	C12—H12A	0.9694
N13—C17	1.351 (4)	C12—H12B	0.9700
N9—H9	0.8597	C14—H14A	0.9694
C1—C2	1.386 (4)	C14—H14B	0.9702
C1—C6	1.404 (4)	C15—H15A	0.9704
C2—C3	1.381 (4)	C15—H15B	0.9694
C3—C4	1.389 (4)
C8—S10—C11	99.74 (15)	C1—C2—H2	121.75
C15—O16—C17	108.2 (2)	C3—C2—H2	121.73
C6—N7—C8	104.3 (2)	C2—C3—H3	118.96
C1—N9—C8	107.0 (2)	C4—C3—H3	119.10
C12—N13—C14	123.3 (3)	C3—C4—H4	119.32
C12—N13—C17	120.2 (3)	C5—C4—H4	119.35
C14—N13—C17	110.2 (2)	C4—C5—H5	120.87
C8—N9—H9	126.57	C6—C5—H5	120.79
C1—N9—H9	126.47	S10—C11—H11A	109.53
N9—C1—C6	105.3 (2)	S10—C11—H11B	109.51
N9—C1—C2	132.3 (3)	C12—C11—H11A	109.50
C2—C1—C6	122.4 (3)	C12—C11—H11B	109.51
C1—C2—C3	116.5 (3)	H11A—C11—H11B	108.10
C2—C3—C4	121.9 (3)	N13—C12—H12A	108.88
C3—C4—C5	121.3 (3)	N13—C12—H12B	108.92
C4—C5—C6	118.3 (3)	C11—C12—H12A	108.95
N7—C6—C5	130.5 (3)	C11—C12—H12B	108.85
C1—C6—C5	119.5 (2)	H12A—C12—H12B	107.78
N7—C6—C1	109.9 (2)	N13—C14—H14A	111.78
N7—C8—N9	113.5 (2)	N13—C14—H14B	111.70
S10—C8—N7	126.3 (2)	C15—C14—H14A	111.82
S10—C8—N9	120.3 (2)	C15—C14—H14B	111.83
S10—C11—C12	110.6 (2)	H14A—C14—H14B	109.49
N13—C12—C11	113.3 (3)	O16—C15—H15A	110.90
N13—C14—C15	100.0 (3)	O16—C15—H15B	110.88
O16—C15—C14	104.2 (3)	C14—C15—H15A	110.88
O18—C17—N13	128.4 (3)	C14—C15—H15B	110.91
O16—C17—O18	121.4 (3)	H15A—C15—H15B	109.00
O16—C17—N13	110.2 (3)
C11—S10—C8—N7	−20.2 (3)	C14—N13—C17—O16	14.2 (4)
C11—S10—C8—N9	159.9 (2)	C14—N13—C12—C11	−68.2 (4)
C8—S10—C11—C12	−166.3 (2)	C12—N13—C17—O16	167.1 (3)
C15—O16—C17—O18	−176.2 (3)	C12—N13—C17—O18	−12.7 (5)
C15—O16—C17—N13	4.0 (3)	N9—C1—C6—N7	−0.1 (3)
C17—O16—C15—C14	−19.3 (3)	N9—C1—C2—C3	−178.2 (3)
C6—N7—C8—S10	179.8 (2)	N9—C1—C6—C5	178.2 (2)
C8—N7—C6—C1	0.3 (3)	C6—C1—C2—C3	0.5 (4)
C6—N7—C8—N9	−0.3 (3)	C2—C1—C6—N7	−179.2 (2)
C8—N7—C6—C5	−177.8 (3)	C2—C1—C6—C5	−0.9 (4)
C1—N9—C8—N7	0.3 (3)	C1—C2—C3—C4	0.6 (5)
C1—N9—C8—S10	−179.83 (18)	C2—C3—C4—C5	−1.4 (5)
C8—N9—C1—C6	−0.1 (3)	C3—C4—C5—C6	1.0 (5)
C8—N9—C1—C2	178.9 (3)	C4—C5—C6—C1	0.1 (4)
C12—N13—C14—C15	−176.6 (3)	C4—C5—C6—N7	178.0 (3)
C14—N13—C17—O18	−165.6 (3)	S10—C11—C12—N13	−55.8 (4)
C17—N13—C12—C11	142.6 (3)	N13—C14—C15—O16	25.6 (3)
C17—N13—C14—C15	−24.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9···N7i	0.86	2.03	2.866 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N9—H9⋯N7i	0.86	2.03	2.866 (3)	165

Symmetry code: (i) .