(4-Benzyl-2-oxo-1,3-oxazolidin-5-yl)methyl methane-sulfonate.

The title compound, C(12)H(15)NO(5)S, features an approximately planar five-membered oxazolidin ring (r.m.s. deviation = 0.045 Å) with the peripheral benzyl and methyl methane-sulfonate residues lying to either side of the plane. In the crystal, N-H⋯O hydrogen bonds, involving one of the sulfur-bound oxo groups as acceptor, lead to the formation of supra-molecular chains along the b axis. These chains are reinforced by C-H⋯O contacts with the carbonyl O atom accepting three such inter-actions. The structure was refined as a racemic twin, with the major component being present 89% of the time.

Related literature

For the use of 1,3-oxazolidin-2-ones as chiral auxiliaries in organic synthesis, see: Evans et al. (1981 ▶); Ager et al. (1996 ▶, 1997 ▶); Hinter­mann & Seebach (1998 ▶). For their biological activity, see: Poce et al. (2008 ▶); Brickner et al. (2008 ▶); Means et al. (2006 ▶); Kaiser et al. (2007 ▶); Clemmet & Markham (2000 ▶); Ebner et al. (2008 ▶); Negwer & Scharnow (2007 ▶); Mai et al. (2003 ▶). For background to their syntheses, see: Ochoa-Terán & Rivero (2008 ▶); Zappia et al. (2007 ▶).

Experimental

Crystal data

C12H15NO5S

M = 285.31

Monoclinic,

a = 8.7332 (5) Å

b = 5.8757 (3) Å

c = 12.9650 (7) Å

β = 103.317 (3)°

V = 647.39 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 120 K

0.26 × 0.08 × 0.02 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.700, T max = 1.000

6748 measured reflections

2587 independent reflections

2266 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.123

S = 1.11

2587 reflections

177 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.36 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809055020/hb5289sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055020/hb5289Isup2.hkl

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

C12H15NO5S	F(000) = 300
Mr = 285.31	Dx = 1.464 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 7909 reflections
a = 8.7332 (5) Å	θ = 2.9–27.5°
b = 5.8757 (3) Å	µ = 0.27 mm−1
c = 12.9650 (7) Å	T = 120 K
β = 103.317 (3)°	Plate, colourless
V = 647.39 (6) Å3	0.26 × 0.08 × 0.02 mm
Z = 2

Nonius KappaCCD area-detector diffractometer	2587 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	2266 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.059
Detector resolution: 9.091 pixels mm-1	θmax = 26.5°, θmin = 3.2°
φ and ω scans	h = −8→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −7→7
Tmin = 0.700, Tmax = 1.000	l = −16→14
6748 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + 1.5106P] where P = (Fo2 + 2Fc2)/3
2587 reflections	(Δ/σ)max < 0.001
177 parameters	Δρmax = 0.33 e Å−3
2 restraints	Δρmin = −0.36 e Å−3

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
S1	0.44667 (11)	0.00547 (18)	0.67229 (8)	0.0215 (2)
O1	0.6105 (3)	0.0327 (6)	0.7186 (2)	0.0284 (7)
O2	0.3629 (4)	−0.1750 (5)	0.7089 (2)	0.0283 (8)
O3	0.4391 (3)	−0.0275 (5)	0.5504 (2)	0.0210 (7)
O4	0.2132 (3)	0.2865 (5)	0.4405 (2)	0.0222 (7)
O5	0.0104 (3)	0.5267 (5)	0.4294 (2)	0.0233 (6)
N1	−0.0074 (4)	0.2084 (6)	0.3228 (3)	0.0223 (8)
H1N	−0.1104 (13)	0.208 (8)	0.305 (4)	0.027*
C1	0.3493 (6)	0.2628 (8)	0.6800 (4)	0.0278 (11)
H1A	0.3625	0.3063	0.7545	0.042*
H1B	0.2370	0.2448	0.6473	0.042*
H1C	0.3937	0.3815	0.6425	0.042*
C2	0.2907 (5)	−0.1031 (7)	0.4793 (3)	0.0207 (9)
H2A	0.2078	−0.1193	0.5196	0.025*
H2B	0.3058	−0.2524	0.4478	0.025*
C3	0.2425 (5)	0.0726 (7)	0.3934 (3)	0.0208 (9)
H3	0.3280	0.0922	0.3544	0.025*
C4	0.0626 (5)	0.3548 (7)	0.3990 (3)	0.0209 (9)
C5	0.0868 (4)	0.0065 (9)	0.3147 (3)	0.0198 (8)
H5	0.0396	−0.1304	0.3410	0.024*
C6	0.1067 (5)	−0.0349 (8)	0.2020 (3)	0.0246 (10)
H6A	0.1506	0.1036	0.1763	0.030*
H6B	0.1824	−0.1607	0.2030	0.030*
C7	−0.0472 (5)	−0.0941 (8)	0.1270 (3)	0.0229 (9)
C8	−0.1231 (5)	0.0627 (8)	0.0526 (3)	0.0289 (11)
H8	−0.0773	0.2083	0.0492	0.035*
C9	−0.2646 (5)	0.0105 (11)	−0.0168 (3)	0.0333 (10)
H9	−0.3146	0.1199	−0.0674	0.040*
C10	−0.3333 (6)	−0.1999 (9)	−0.0126 (4)	0.0326 (11)
H10	−0.4308	−0.2360	−0.0597	0.039*
C11	−0.2577 (6)	−0.3580 (8)	0.0615 (4)	0.0301 (11)
H11	−0.3037	−0.5033	0.0653	0.036*
C12	−0.1161 (5)	−0.3054 (8)	0.1297 (4)	0.0267 (10)
H12	−0.0651	−0.4160	0.1792	0.032*

	U11	U22	U33	U12	U13	U23
S1	0.0215 (5)	0.0219 (5)	0.0206 (5)	−0.0014 (5)	0.0037 (4)	−0.0012 (5)
O1	0.0221 (14)	0.036 (2)	0.0237 (15)	−0.0046 (16)	−0.0008 (11)	−0.0039 (15)
O2	0.0333 (19)	0.0263 (18)	0.0235 (17)	−0.0045 (15)	0.0030 (14)	0.0029 (14)
O3	0.0161 (13)	0.0277 (18)	0.0178 (13)	−0.0015 (13)	0.0007 (10)	−0.0043 (13)
O4	0.0176 (15)	0.0207 (15)	0.0260 (16)	0.0016 (12)	0.0001 (12)	−0.0014 (13)
O5	0.0240 (14)	0.0174 (16)	0.0294 (15)	0.0013 (14)	0.0082 (12)	0.0000 (14)
N1	0.0172 (18)	0.026 (2)	0.024 (2)	0.0008 (15)	0.0046 (15)	−0.0014 (15)
C1	0.032 (3)	0.021 (2)	0.031 (3)	0.000 (2)	0.009 (2)	−0.005 (2)
C2	0.020 (2)	0.022 (2)	0.019 (2)	0.0003 (17)	0.0018 (17)	−0.0022 (17)
C3	0.020 (2)	0.014 (2)	0.028 (2)	−0.0019 (15)	0.0052 (17)	−0.0025 (16)
C4	0.022 (2)	0.021 (2)	0.021 (2)	−0.0033 (18)	0.0066 (17)	0.0057 (17)
C5	0.0181 (17)	0.0195 (19)	0.0217 (19)	0.001 (2)	0.0041 (14)	0.006 (2)
C6	0.022 (2)	0.026 (3)	0.025 (2)	0.0009 (18)	0.0060 (17)	0.0007 (18)
C7	0.027 (2)	0.026 (2)	0.017 (2)	0.0023 (18)	0.0080 (18)	−0.0022 (17)
C8	0.035 (2)	0.029 (3)	0.024 (2)	−0.001 (2)	0.0093 (19)	0.0006 (18)
C9	0.041 (2)	0.035 (3)	0.020 (2)	0.004 (3)	0.0000 (18)	−0.003 (3)
C10	0.027 (2)	0.043 (3)	0.027 (3)	0.003 (2)	0.003 (2)	−0.007 (2)
C11	0.033 (3)	0.024 (3)	0.034 (3)	−0.005 (2)	0.008 (2)	−0.003 (2)
C12	0.029 (2)	0.028 (2)	0.022 (2)	−0.001 (2)	0.0024 (18)	0.0016 (19)

S1—O1	1.427 (3)	C3—H3	1.0000
S1—O2	1.430 (3)	C5—C6	1.529 (5)
S1—O3	1.578 (3)	C5—H5	1.0000
S1—C1	1.749 (5)	C6—C7	1.507 (6)
O3—C2	1.475 (5)	C6—H6A	0.9900
O4—C4	1.362 (5)	C6—H6B	0.9900
O4—C3	1.445 (5)	C7—C12	1.383 (6)
O5—C4	1.210 (5)	C7—C8	1.387 (6)
N1—C4	1.346 (6)	C8—C9	1.385 (6)
N1—C5	1.462 (6)	C8—H8	0.9500
N1—H1N	0.875 (10)	C9—C10	1.381 (8)
C1—H1A	0.9800	C9—H9	0.9500
C1—H1B	0.9800	C10—C11	1.390 (7)
C1—H1C	0.9800	C10—H10	0.9500
C2—C3	1.506 (5)	C11—C12	1.379 (7)
C2—H2A	0.9900	C11—H11	0.9500
C2—H2B	0.9900	C12—H12	0.9500
C3—C5	1.550 (5)
O1—S1—O2	118.9 (2)	N1—C4—O4	109.6 (4)
O1—S1—O3	103.99 (16)	N1—C5—C6	112.8 (3)
O2—S1—O3	109.53 (18)	N1—C5—C3	99.9 (4)
O1—S1—C1	109.4 (2)	C6—C5—C3	113.2 (3)
O2—S1—C1	109.2 (2)	N1—C5—H5	110.2
O3—S1—C1	104.8 (2)	C6—C5—H5	110.2
C2—O3—S1	119.4 (2)	C3—C5—H5	110.2
C4—O4—C3	109.8 (3)	C7—C6—C5	111.9 (3)
C4—N1—C5	113.8 (4)	C7—C6—H6A	109.2
C4—N1—H1N	117 (3)	C5—C6—H6A	109.2
C5—N1—H1N	123 (3)	C7—C6—H6B	109.2
S1—C1—H1A	109.5	C5—C6—H6B	109.2
S1—C1—H1B	109.5	H6A—C6—H6B	107.9
H1A—C1—H1B	109.5	C12—C7—C8	118.2 (4)
S1—C1—H1C	109.5	C12—C7—C6	121.3 (4)
H1A—C1—H1C	109.5	C8—C7—C6	120.5 (4)
H1B—C1—H1C	109.5	C9—C8—C7	121.1 (5)
O3—C2—C3	108.1 (3)	C9—C8—H8	119.4
O3—C2—H2A	110.1	C7—C8—H8	119.4
C3—C2—H2A	110.1	C10—C9—C8	120.2 (5)
O3—C2—H2B	110.1	C10—C9—H9	119.9
C3—C2—H2B	110.1	C8—C9—H9	119.9
H2A—C2—H2B	108.4	C9—C10—C11	118.9 (4)
O4—C3—C2	109.3 (3)	C9—C10—H10	120.5
O4—C3—C5	106.4 (3)	C11—C10—H10	120.5
C2—C3—C5	111.6 (3)	C12—C11—C10	120.4 (5)
O4—C3—H3	109.8	C12—C11—H11	119.8
C2—C3—H3	109.8	C10—C11—H11	119.8
C5—C3—H3	109.8	C11—C12—C7	121.1 (4)
O5—C4—N1	129.1 (4)	C11—C12—H12	119.5
O5—C4—O4	121.3 (4)	C7—C12—H12	119.5
O1—S1—O3—C2	168.8 (3)	C2—C3—C5—N1	123.5 (4)
O2—S1—O3—C2	40.7 (4)	O4—C3—C5—C6	124.6 (4)
C1—S1—O3—C2	−76.4 (3)	C2—C3—C5—C6	−116.3 (4)
S1—O3—C2—C3	122.4 (3)	N1—C5—C6—C7	−66.3 (5)
C4—O4—C3—C2	−121.3 (4)	C3—C5—C6—C7	−178.9 (4)
C4—O4—C3—C5	−0.7 (4)	C5—C6—C7—C12	−73.9 (5)
O3—C2—C3—O4	−62.6 (4)	C5—C6—C7—C8	106.5 (5)
O3—C2—C3—C5	180.0 (3)	C12—C7—C8—C9	0.4 (6)
C5—N1—C4—O5	−174.4 (4)	C6—C7—C8—C9	−180.0 (4)
C5—N1—C4—O4	7.3 (5)	C7—C8—C9—C10	0.3 (7)
C3—O4—C4—O5	177.7 (4)	C8—C9—C10—C11	−0.5 (7)
C3—O4—C4—N1	−3.8 (5)	C9—C10—C11—C12	−0.1 (7)
C4—N1—C5—C6	−127.6 (4)	C10—C11—C12—C7	0.9 (7)
C4—N1—C5—C3	−7.1 (4)	C8—C7—C12—C11	−1.0 (7)
O4—C3—C5—N1	4.4 (4)	C6—C7—C12—C11	179.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.88 (2)	2.28 (2)	3.113 (5)	160 (4)
C1—H1B···O5ii	0.98	2.51	3.428 (6)	155
C2—H2A···O5ii	0.99	2.32	3.214 (5)	150
C5—H5···O5iii	1.00	2.36	3.326 (6)	162
C6—H6B···O1iv	0.99	2.59	3.528 (6)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.88 (2)	2.28 (2)	3.113 (5)	160 (4)
C1—H1B⋯O5ii	0.98	2.51	3.428 (6)	155
C2—H2A⋯O5ii	0.99	2.32	3.214 (5)	150
C5—H5⋯O5iii	1.00	2.36	3.326 (6)	162
C6—H6B⋯O1iv	0.99	2.59	3.528 (6)	158

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