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

In the title compound, C(12)H(13)N(3)O(2), the dihedral angle between the oxazolone ring and the benzimidazole unit is 45.0 (5)°, exhibiting a staggered conformation at the Cα-Cβ bond. In the crystal, a strong N-H⋯N hydrogen bond links the mol-ecules into a C(4) chain along the c axis while a C-H⋯O hydrogen-bonding inter-action generates a C(5) chain along the a axis, i.e. perpendicular to the other chain.

Related literature

For the therapeutic activity of benzimidazole and oxazolid­in­one derivatives, see: Niño et al. 2001 ▶; Siva Kumar et al. 2010 ▶; Zappia et al. 2007 ▶. For the drug linezolid [systematic name (S)-N-({3-[3-fluoro-4-(morpholin-4-yl)phen­yl]-2-oxo-1,3-oxazolidin-5-yl}meth­yl)acetamide], see: Brickner et al. (2008 ▶). For asymmetry of the exocyclic angles in oxazolone rings, see: Grassi et al. (2001 ▶). For the structures of benzimidazole and oxazolidine, see: Totsatitpaisan et al. (2008 ▶); Wouters et al. (1997 ▶).

Experimental

Crystal data

C12H13N3O2

M = 231.25

Monoclinic,

a = 6.0940 (2) Å

b = 18.1570 (6) Å

c = 10.0740 (3) Å

β = 90.696 (1)°

V = 1114.59 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.51 × 0.43 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

34135 measured reflections

1951 independent reflections

1830 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.089

S = 1.05

1951 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012256/bh2341sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012256/bh2341Isup2.hkl

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

C12H13N3O2	F(000) = 488
Mr = 231.25	Dx = 1.378 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9799 reflections
a = 6.0940 (2) Å	θ = 2.3–30.0°
b = 18.1570 (6) Å	µ = 0.10 mm−1
c = 10.0740 (3) Å	T = 296 K
β = 90.696 (1)°	Prism, colourless
V = 1114.59 (6) Å3	0.51 × 0.43 × 0.21 mm
Z = 4

Bruker APEXII CCD diffractometer	Rint = 0.021
graphite	θmax = 25°, θmin = 3.0°
φ and ω scans	h = −7→7
34135 measured reflections	k = −21→21
1951 independent reflections	l = −11→11
1830 reflections with I > 2σ(I)

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)] = 0.033	H-atom parameters constrained
wR(F2) = 0.089	w = 1/[σ2(Fo2) + (0.0448P)2 + 0.2758P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1951 reflections	Δρmax = 0.21 e Å−3
155 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
0 constraints	Extinction coefficient: 0.031 (3)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
C2	0.68193 (19)	0.18737 (6)	0.48419 (11)	0.0360 (3)
C3	0.8441 (2)	0.14478 (8)	0.54393 (13)	0.0495 (3)
H3	0.8494	0.1375	0.6353	0.059*
C4	0.9971 (2)	0.11369 (8)	0.46129 (15)	0.0556 (4)
H4	1.1078	0.0845	0.4978	0.067*
C5	0.9903 (2)	0.12476 (8)	0.32465 (15)	0.0523 (4)
H5	1.0971	0.1032	0.2722	0.063*
C6	0.8292 (2)	0.16686 (7)	0.26555 (12)	0.0452 (3)
H6	0.825	0.1739	0.1741	0.054*
C7	0.67213 (19)	0.19869 (6)	0.34697 (11)	0.0350 (3)
C9	0.40064 (19)	0.25761 (6)	0.42951 (11)	0.0352 (3)
C10	0.2094 (2)	0.30701 (7)	0.44963 (13)	0.0439 (3)
H10A	0.1152	0.286	0.5167	0.053*
H10B	0.1252	0.3104	0.3675	0.053*
C11	0.2802 (2)	0.38413 (7)	0.49276 (13)	0.0439 (3)
H11A	0.1517	0.4119	0.5187	0.053*
H11B	0.3766	0.3802	0.5698	0.053*
C13	0.6099 (2)	0.43147 (7)	0.38402 (14)	0.0457 (3)
C16	0.4669 (3)	0.49106 (10)	0.20459 (17)	0.0682 (5)
H16A	0.4673	0.4673	0.1184	0.082*
H16B	0.455	0.5439	0.1917	0.082*
C17	0.2788 (3)	0.46309 (11)	0.28639 (17)	0.0693 (5)
H17A	0.193	0.5033	0.3221	0.083*
H17B	0.1835	0.4308	0.235	0.083*
N1	0.50576 (16)	0.22534 (6)	0.53358 (9)	0.0379 (3)
H1	0.4689	0.2281	0.6156	0.045*
N8	0.49276 (16)	0.24297 (6)	0.31510 (9)	0.0376 (3)
N12	0.39262 (16)	0.42375 (6)	0.38915 (11)	0.0440 (3)
O14	0.74742 (17)	0.40717 (7)	0.45882 (13)	0.0730 (4)
O15	0.66295 (17)	0.47348 (6)	0.27768 (11)	0.0606 (3)

	U11	U22	U33	U12	U13	U23
C2	0.0400 (6)	0.0367 (6)	0.0314 (6)	−0.0057 (5)	0.0019 (5)	−0.0004 (5)
C3	0.0553 (8)	0.0536 (8)	0.0394 (7)	0.0006 (6)	−0.0045 (6)	0.0092 (6)
C4	0.0496 (8)	0.0541 (8)	0.0630 (9)	0.0100 (6)	−0.0035 (7)	0.0054 (7)
C5	0.0466 (7)	0.0547 (8)	0.0558 (8)	0.0051 (6)	0.0086 (6)	−0.0087 (6)
C6	0.0471 (7)	0.0533 (8)	0.0352 (6)	−0.0018 (6)	0.0067 (5)	−0.0050 (5)
C7	0.0379 (6)	0.0370 (6)	0.0300 (6)	−0.0057 (5)	0.0017 (5)	−0.0015 (4)
C9	0.0360 (6)	0.0383 (6)	0.0315 (6)	−0.0071 (5)	0.0025 (5)	−0.0013 (5)
C10	0.0346 (6)	0.0494 (7)	0.0478 (7)	−0.0031 (5)	0.0067 (5)	−0.0006 (6)
C11	0.0395 (7)	0.0483 (7)	0.0440 (7)	0.0040 (5)	0.0050 (5)	−0.0045 (5)
C13	0.0392 (7)	0.0457 (7)	0.0521 (7)	−0.0010 (5)	0.0014 (6)	−0.0063 (6)
C16	0.0762 (11)	0.0666 (10)	0.0618 (10)	0.0016 (8)	0.0012 (8)	0.0156 (8)
C17	0.0548 (9)	0.0894 (12)	0.0634 (10)	−0.0038 (8)	−0.0136 (7)	0.0212 (9)
N1	0.0433 (6)	0.0459 (6)	0.0246 (5)	−0.0031 (4)	0.0056 (4)	−0.0011 (4)
N8	0.0386 (5)	0.0459 (6)	0.0283 (5)	−0.0023 (4)	0.0020 (4)	0.0011 (4)
N12	0.0341 (5)	0.0451 (6)	0.0527 (6)	0.0013 (4)	−0.0023 (5)	0.0048 (5)
O14	0.0389 (6)	0.0963 (9)	0.0835 (8)	0.0045 (5)	−0.0103 (5)	0.0128 (7)
O15	0.0534 (6)	0.0681 (7)	0.0605 (6)	−0.0114 (5)	0.0104 (5)	0.0016 (5)

C2—N1	1.374 (2)	C10—H10A	0.97
C2—C3	1.387 (2)	C10—H10B	0.97
C2—C7	1.398 (2)	C11—N12	1.447 (2)
C3—C4	1.378 (2)	C11—H11A	0.97
C3—H3	0.93	C11—H11B	0.97
C4—C5	1.391 (2)	C13—O14	1.204 (2)
C4—H4	0.93	C13—N12	1.333 (2)
C5—C6	1.374 (2)	C13—O15	1.357 (2)
C5—H5	0.93	C16—O15	1.432 (2)
C6—C7	1.3934 (17)	C16—C17	1.508 (2)
C6—H6	0.93	C16—H16A	0.97
C7—N8	1.391 (2)	C16—H16B	0.97
C9—N8	1.315 (2)	C17—N12	1.430 (2)
C9—N1	1.355 (2)	C17—H17A	0.97
C9—C10	1.487 (2)	C17—H17B	0.97
C10—C11	1.5269 (19)	N1—H1	0.86
N1—C2—C3	132.72 (11)	N12—C11—H11A	109.1
N1—C2—C7	105.08 (10)	C10—C11—H11A	109.1
C3—C2—C7	122.20 (12)	N12—C11—H11B	109.1
C4—C3—C2	116.75 (12)	C10—C11—H11B	109.1
C4—C3—H3	121.6	H11A—C11—H11B	107.8
C2—C3—H3	121.6	O14—C13—N12	128.4 (1)
C3—C4—C5	121.75 (13)	O14—C13—O15	121.9 (1)
C3—C4—H4	119.1	N12—C13—O15	109.6 (1)
C5—C4—H4	119.1	O15—C16—C17	106.2 (1)
C6—C5—C4	121.43 (13)	O15—C16—H16A	110.5
C6—C5—H5	119.3	C17—C16—H16A	110.5
C4—C5—H5	119.3	O15—C16—H16B	110.5
C5—C6—C7	117.89 (12)	C17—C16—H16B	110.5
C5—C6—H6	121.1	H16A—C16—H16B	108.7
C7—C6—H6	121.1	N12—C17—C16	101.45 (13)
N8—C7—C6	130.32 (11)	N12—C17—H17A	111.5
N8—C7—C2	109.70 (10)	C16—C17—H17A	111.5
C6—C7—C2	119.98 (11)	N12—C17—H17B	111.5
N8—C9—N1	112.8 (1)	C16—C17—H17B	111.5
N8—C9—C10	125.8 (1)	H17A—C17—H17B	109.3
N1—C9—C10	121.3 (1)	C9—N1—C2	107.50 (9)
C9—C10—C11	111.88 (10)	C9—N1—H1	126.2
C9—C10—H10A	109.2	C2—N1—H1	126.2
C11—C10—H10A	109.2	C9—N8—C7	104.90 (10)
C9—C10—H10B	109.2	C13—N12—C17	113.11 (12)
C11—C10—H10B	109.2	C13—N12—C11	124.01 (11)
H10A—C10—H10B	107.9	C17—N12—C11	122.74 (11)
N12—C11—C10	112.67 (10)	C13—O15—C16	109.01 (11)
N1—C2—C3—C4	179.30 (13)	C3—C2—N1—C9	−179.94 (13)
C7—C2—C3—C4	−0.01 (19)	C7—C2—N1—C9	−0.55 (12)
C2—C3—C4—C5	0.4 (2)	N1—C9—N8—C7	−0.69 (13)
C3—C4—C5—C6	−0.5 (2)	C10—C9—N8—C7	176.10 (11)
C4—C5—C6—C7	0.3 (2)	C6—C7—N8—C9	−179.88 (12)
C5—C6—C7—N8	−179.73 (12)	C2—C7—N8—C9	0.32 (13)
C5—C6—C7—C2	0.05 (18)	O14—C13—N12—C17	177.42 (16)
N1—C2—C7—N8	0.15 (13)	O15—C13—N12—C17	−2.03 (17)
C3—C2—C7—N8	179.62 (11)	O14—C13—N12—C11	1.5 (2)
N1—C2—C7—C6	−179.68 (11)	O15—C13—N12—C11	−177.92 (11)
C3—C2—C7—C6	−0.20 (18)	C16—C17—N12—C13	5.96 (19)
N8—C9—C10—C11	−97.20 (14)	C16—C17—N12—C11	−178.09 (13)
N1—C9—C10—C11	79.34 (14)	C10—C11—N12—C13	−101.12 (15)
C9—C10—C11—N12	68.0 (1)	C10—C11—N12—C17	83.38 (16)
O15—C16—C17—N12	−7.44 (18)	O14—C13—O15—C16	177.27 (14)
N8—C9—N1—C2	0.81 (13)	N12—C13—O15—C16	−3.24 (16)
C10—C9—N1—C2	−176.15 (10)	C17—C16—O15—C13	6.84 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N8i	0.86	2.08	2.8959 (13)	158.
C11—H11A···O14ii	0.97	2.53	3.2876 (16)	135.
C11—H11B···O14	0.97	2.58	2.9019 (16)	100.
C3—H3···O15i	0.93	2.73	3.3820 (17)	128.
C5—H5···O15iii	0.93	2.82	3.6229 (17)	145.
C6—H6···O14iv	0.93	2.66	3.4008 (17)	137.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N8i	0.86	2.08	2.8959 (13)	158
C11—H11A⋯O14ii	0.97	2.53	3.2876 (16)	135

Symmetry codes: (i) ; (ii) .