3-[2-(1H-Benzimidazol-2-ylsulfan­yl)eth­yl]-1,3-oxazolidin-2-one

Moussaif, A.; Essassi, E.M.; Lazar, S.; Zouihri, H.; Leger, J.M.

doi:10.1107/S1600536810045897

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3137

https://doi.org/10.1107/S1600536810045897

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3-[2-(1H-Benzimidazol-2-ylsulfanyl)ethyl]-1,3-oxazolidin-2-one

Ahmed Moussaif,^a El Mokhtar Essassi,^b Said Lazar,^c ^* Hafid Zouihri ^d and Jean Michel Leger ^e

^aCentre National de l'Energie, des Sciences et des Techniques Nucléaires, Maamoura Kenitra, Morocco, ^bInstitut of Nanomaterials and Nanotechnology, INANOTECH, Avenue de l Armée, Royale, Rabat, Morocco, ^cLaboratoire de Biochimie, Environnement et Agroalimentaire (URAC 36), Faculté des Sciences et Techniques Mohammedia, Université Hassan II, Mohammedia-Casablana, BP 146, 20800 Mohammedia, Morocco, ^dLaboratoires de Diffraction des Rayons X, Centre Nationale pour la Recherche Scientifique et Technique, Rabat, Morocco, and ^eLaboratoire de Chimie Physique et Minérale, Service de Cristallographie, Université Victor Segalen Bordeaux II, France
^*Correspondence e-mail: lazar_said@yahoo.fr

(Received 4 November 2010; accepted 8 November 2010; online 13 November 2010)

In the title compound, C₁₂H₁₃N₃O₂S, 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, molecules are linked by intermolecular 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_r = 263.31
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.138
S = 1.04
2065 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045897/dn2620Isup2.hkl

checkCIF report

Comment top

The synthesis of new oxindole derivatives having an oxazolindin-2-one unit has been detailed in recent reports (Al Subari et al., 2010a,b; Ahoya et al., 2010; Ballo et al.,2010).

In the new oxazolidin-2-one, C₁₂H₁₃N₃O₂S, the dihedral angle between the 1H-benzimidazole ring and the 1,3-oxazolidin-2-one mean plane is: 69.85 (13)° (Fig.1). The oxazolidin ring is not planar but display envelope conformation on C14 with puckering parameters Q(2) = 0.258 (3) Å and φ(2) = 63.3 (7) ° (Cremer & Pople, 1975).

In the crystal structure, the molecules are linked by intermolecular N—H···N hydrogen bonds forming a chain parallel to the b axis (Table 1, Fig. 2).

Related literature top

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 top

To the solution of benzimidazole-2-thione (1,35 g, 9 mmoles) and dichloroethyl amine hydrochloride (2,41 g, 13.5 mmoles) in dimethylformamide (80 ml) were added potassium carbonate (4,14 g, 30 mmoles) and tetra-n-butylammonium bromide (0,10 g, 0,3 mmoles). The resulting mixture was refluxed for 4 h. After filtering the solvent was removed and the residue was purified by column chromatography on silica gel (Hexane/AcOEt: 60/40) to afford the title compound.

Yield = 55%

F = 230–232 °C (ethanol-water).

RMN ¹H (d p.p.m.): 3.57: SCH₂ (2H, t, J = 6.25 Hz); 3,36: NCH₂ (4H, m); 4.23: OCH₂ (4H, t, J = 6,25 Hz); 7.30–7.70: CH (benzénique)(8H, m); 11.57: NH (1H, s)

Mass Spectre IE: M⁺ (m/z=263).

Structure description top

The synthesis of new oxindole derivatives having an oxazolindin-2-one unit has been detailed in recent reports (Al Subari et al., 2010a,b; Ahoya et al., 2010; Ballo et al.,2010).

In the crystal structure, the molecules are linked by intermolecular N—H···N hydrogen bonds forming a chain parallel to the b axis (Table 1, Fig. 2).

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).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: CAD-4 Software (Enraf–Nonius, 1989); program(s) used to solve structure: SHELXL97 (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).

Figures top

	Fig. 1. Molecular view of the title compound showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Partial packing view showing the chain formed by N-H···N hydrogen bondings. H atoms not involved in hydrogen bonds have been omitted for clarity. [Symmetry code: (i) -x+1/2, y+1/2, z ]

3-[2-(1H-Benzimidazol-2-ylsulfanyl)ethyl]-1,3-oxazolidin-2-one top

Crystal data top

C₁₂H₁₃N₃O₂S	F(000) = 1104
M_r = 263.31	D_x = 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

Data collection top

Enraf–Nonius CAD-4 diffractometer	1580 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 64.9°, θ_min = 3.0°
ω–2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = 0→11
T_min = 0.589, T_max = 0.891	l = 0→34
2065 measured reflections	2 standard reflections every 90 min
2065 independent reflections	intensity decay: none

Refinement top

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(F_o²) + (0.0753P)² + 1.285P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2065 reflections	Δρ_max = 0.50 e Å⁻³
164 parameters	Δρ_min = −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)

Crystal data top

C₁₂H₁₃N₃O₂S	V = 2429.3 (5) Å³
M_r = 263.31	Z = 8
Orthorhombic, Pbca	Cu Kα radiation
a = 8.258 (1) Å	µ = 2.37 mm⁻¹
b = 10.074 (1) Å	T = 296 K
c = 29.201 (3) Å	0.25 × 0.10 × 0.05 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1580 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.000
T_min = 0.589, T_max = 0.891	2 standard reflections every 90 min
2065 measured reflections	intensity decay: none
2065 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.04	Δρ_max = 0.50 e Å⁻³
2065 reflections	Δρ_min = −0.26 e Å⁻³
164 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₃N₃O₂S
M_r	263.31
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	8.258 (1), 10.074 (1), 29.201 (3)
V (Å³)	2429.3 (5)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	2.37
Crystal size (mm)	0.25 × 0.10 × 0.05

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.589, 0.891
No. of measured, independent and observed [I > 2σ(I)] reflections	2065, 2065, 1580
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.587

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.138, 1.04
No. of reflections	2065
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.26

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y+1/2, z.

References

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