(R)-[(R)-3-Benzyl-2-oxooxazolidin-4-yl][4-(methyl­sulfon­yl)phen­yl]methyl acetate

Li, F.; Zhao, M.-Z.; Jin, C.-H.; Zou, J.-W.

doi:10.1107/S1600536814009106

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Page o606

doi:10.1107/S1600536814009106

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(R)-[(R)-3-Benzyl-2-oxooxazolidin-4-yl][4-(methylsulfonyl)phenyl]methyl acetate

Feng Li,^a Ming-Zhong Zhao,^b Chun-Hua Jin ^a ^* and Jian-Wei Zou ^a

^aSchool of Biological & Chemical Engineering, Ningbo Institute of Technology, Zhejiang University, Ningbo 315100, People's Republic of China, and ^bNingbo Ocean & Fishery Bureau, Ningbo 315100, People's Republic of China
^*Correspondence e-mail: chjin641@163.com

(Received 26 March 2014; accepted 22 April 2014; online 26 April 2014)

The structure of the title compound, C₂₀H₂₁NO₆S, is of interest with respect to its antibacterial properties. The oxazolidine ring makes dihedral angles of 79.63 (14) and 56.16 (12)° with the phenyl and benzene rings, respectively, while the phenyl and benzene rings make a dihedral angle of 64.37 (13)°. In the crystal, non-classical C—H⋯O hydrogen bonds link adjacent molecules along the c axis.

CCDC reference: 998863

Related literature

For the original synthesis of the title compound, see: Li et al. (2011 ). For inversion of the configuration of the sulfonyloxy moiety, see: Shi et al. (2010 ). For background to the anti-bacterial properties of thiamphenicol-like compounds, see: Nagabhushan (1980 , 1981 ); Jommi et al. (1985 ).

Experimental

Crystal data

C₂₀H₂₁NO₆S
M_r = 403.44
Monoclinic, P 2₁
a = 5.837 (3) Å
b = 21.021 (10) Å
c = 7.884 (4) Å
β = 100.256 (7)°
V = 952.0 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.30 × 0.25 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.940, T_max = 0.968
6495 measured reflections
3658 independent reflections
3254 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.091
S = 1.02
3658 reflections
255 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.17 e Å⁻³
Absolute structure: Flack (1983 ), 1356 Friedel pairs
Absolute structure parameter: −0.06 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O4ⁱ	0.97	2.52	3.373 (3)	147
C10—H10⋯O6ⁱ	0.98	2.54	3.384 (3)	144
C13—H13C⋯O1ⁱⁱ	0.96	2.55	3.305 (3)	135
Symmetry codes: (i) x, y, z+1; (ii) x-1, y, z-1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 998863

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814009106/hg5390sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814009106/hg5390Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814009106/hg5390Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536814009106/hg5390Isup4.cml

checkCIF report

Comment top

During the study on the synthesis of florfenicol, a class of antibiotics with pronounced broad-spectrum antibacterial activity, (Nagabhushan, 1980 & Jommi et al., 1985). the title compound was produced and is a key intermediate in the synthetic route to florfenicol (Li et al., 2011). The title compound was synthesized through the nucleophilic substitution reaction of (S)-((R)-3-benzyl-2-oxooxazolidin-4-yl)(4-(methylsulfonyl) phenyl)methylmethane sulfonate. Here we report the crystal structure of the title compound.

Fig. 1 shows the molecular structure of the title compound. The enantiomer was selected on the basis of the configuration of the starting material. All chiral carbon atoms (C10 and C11) are R-configuration. Only one molecule is included in the asymmetrical unit of this compound (Fig. 1). All the bond lengths and relevant angles are in the typical ranges. Although there is no –NH or –OH group available in the structure to form strong hydrogen bonds, the C atoms are involved in the formation of non-classical inter-molecular C—H···O hydrogen bonds (Fig 2).

Experimental top

The literature procedure according to Li et al. (2011) was followed. A solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (700 mg, 4.56 mmol) and glacial acetic acid (550 mg, 9.11 mmol) in anhydrous toluene (5 mL) was stirred for 1.5 h at room temperature. (S)-((R)-3-benzyl-2-oxooxazolidin-4-yl)(4-(methylsulfonyl)phenyl)methylmethanesulfonate was added and the reaction mixture was heated to 363 K for 8 h. The resulting mixture was cooled to r.t., diluted with CH₂Cl₂ (40 mL) and washed with 2M aq. HCl (30 mL), 10% aq. K₂CO₃ (30 mL), and brine (30 mL) successively. The organic phase was dried over Na₂SO₄, concentrated in vacuo. The residue was purified by flash chromatography to afford the title compound 850 mg (92%) as a white solid. Suitable crystals for X-ray experiments were obtained by slow evaporation from an AcOEt/CHCl₃ solution at room temperature.

Refinement top

Hydrogen atoms bonded to the carbon atoms were placed in calculated positions and refined as riding mode, with C—H = 0.93Å (methane) or 0.96Å (methyl) and U_iso(H) = 1.2U_eq (C_methane) or U_iso(H) = 1.5U_eq (C_methyl).

Related literature top

For the original synthesis of the title compound, see: Li et al. (2011). For the inversion of configuration, see: Shi et al. (2010). For background to the anti-bacterial properties of thiamphenicol-like compounds, see: Nagabhushan (1980, 1981); Jommi et al. (1985).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The ORTEP view of the title compound with 30% probability level ellipsoids.
	Fig. 2. The molecular packing diagram of the title compound.

(R)-[(R)-3-Benzyl-2-oxooxazolidin-4-yl][4-(methylsulfonyl)phenyl]methyl acetate top

Crystal data top

C₂₀H₂₁NO₆S	F(000) = 424
M_r = 403.44	D_x = 1.407 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2349 reflections
a = 5.837 (3) Å	θ = 2.6–25.3°
b = 21.021 (10) Å	µ = 0.21 mm⁻¹
c = 7.884 (4) Å	T = 296 K
β = 100.256 (7)°	Block, colourless
V = 952.0 (7) Å³	0.30 × 0.25 × 0.16 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	3658 independent reflections
Radiation source: fine-focus sealed tube	3254 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
phi and ω scans	θ_max = 27.8°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→7
T_min = 0.940, T_max = 0.968	k = −19→27
6495 measured reflections	l = −10→9

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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0516P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3658 reflections	Δρ_max = 0.14 e Å⁻³
255 parameters	Δρ_min = −0.17 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1356 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.06 (6)

Crystal data top

C₂₀H₂₁NO₆S	V = 952.0 (7) Å³
M_r = 403.44	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.837 (3) Å	µ = 0.21 mm⁻¹
b = 21.021 (10) Å	T = 296 K
c = 7.884 (4) Å	0.30 × 0.25 × 0.16 mm
β = 100.256 (7)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3658 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3254 reflections with I > 2σ(I)
T_min = 0.940, T_max = 0.968	R_int = 0.022
6495 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.091	Δρ_max = 0.14 e Å⁻³
S = 1.02	Δρ_min = −0.17 e Å⁻³
3658 reflections	Absolute structure: Flack (1983), 1356 Friedel pairs
255 parameters	Absolute structure parameter: −0.06 (6)
1 restraint

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	0.2302 (4)	1.05248 (14)	1.2707 (4)	0.0558 (6)
H1	0.1259	1.0324	1.3295	0.067*
C2	0.1916 (6)	1.11380 (17)	1.2191 (5)	0.0781 (10)
H2	0.0605	1.1349	1.2422	0.094*
C3	0.3431 (7)	1.14521 (16)	1.1331 (5)	0.0833 (11)
H3	0.3155	1.1872	1.0981	0.100*
C4	0.5382 (6)	1.11300 (16)	1.0994 (4)	0.0701 (9)
H4	0.6428	1.1335	1.0417	0.084*
C5	0.5769 (4)	1.05031 (13)	1.1517 (3)	0.0506 (6)
H5	0.7077	1.0290	1.1290	0.061*
C6	0.4227 (4)	1.01946 (11)	1.2373 (3)	0.0395 (5)
C7	0.4569 (4)	0.95231 (11)	1.3036 (3)	0.0418 (5)
H7A	0.5095	0.9540	1.4274	0.050*
H7B	0.3070	0.9311	1.2832	0.050*
C8	0.8331 (4)	0.90008 (12)	1.3230 (3)	0.0418 (5)
C9	0.7678 (4)	0.82331 (14)	1.1163 (3)	0.0491 (6)
H9A	0.7290	0.7800	1.1428	0.059*
H9B	0.8324	0.8231	1.0112	0.059*
C10	0.5504 (3)	0.86602 (11)	1.0957 (3)	0.0347 (4)
H10	0.4169	0.8418	1.1206	0.042*
C11	0.4959 (3)	0.89357 (10)	0.9143 (2)	0.0325 (4)
H11	0.6286	0.9188	0.8923	0.039*
C12	0.2825 (4)	0.98383 (11)	0.7947 (3)	0.0401 (5)
C13	0.0631 (5)	1.02073 (14)	0.7899 (3)	0.0567 (7)
H13A	0.0890	1.0643	0.7625	0.085*
H13B	0.0163	1.0185	0.9005	0.085*
H13C	−0.0571	1.0031	0.7037	0.085*
C14	0.4399 (3)	0.84297 (10)	0.7772 (2)	0.0329 (4)
C15	0.2402 (4)	0.80602 (13)	0.7690 (3)	0.0453 (6)
H15	0.1481	0.8107	0.8531	0.054*
C16	0.1773 (4)	0.76262 (12)	0.6378 (3)	0.0435 (5)
H16	0.0425	0.7386	0.6324	0.052*
C17	0.3164 (3)	0.75514 (10)	0.5144 (2)	0.0343 (4)
C18	0.5208 (4)	0.78958 (12)	0.5248 (3)	0.0394 (5)
H18	0.6177	0.7831	0.4447	0.047*
C19	0.5795 (3)	0.83348 (11)	0.6545 (3)	0.0380 (5)
H19	0.7151	0.8572	0.6600	0.046*
C20	0.4084 (5)	0.63552 (13)	0.3899 (3)	0.0563 (6)
H20A	0.3814	0.6170	0.4959	0.084*
H20B	0.5685	0.6483	0.4022	0.084*
H20C	0.3739	0.6048	0.2988	0.084*
N1	0.6212 (3)	0.91344 (9)	1.2290 (2)	0.0373 (4)
O1	0.9319 (3)	0.92759 (11)	1.4488 (2)	0.0607 (5)
O2	0.9295 (3)	0.84974 (9)	1.2545 (2)	0.0530 (4)
O3	0.2955 (2)	0.93443 (7)	0.90796 (18)	0.0374 (3)
O4	0.4311 (3)	0.99426 (10)	0.7128 (2)	0.0566 (5)
O5	−0.0080 (3)	0.68428 (10)	0.3436 (2)	0.0585 (5)
O6	0.2809 (3)	0.73099 (10)	0.1869 (2)	0.0574 (5)
S1	0.22845 (9)	0.70219 (3)	0.34050 (6)	0.03925 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0543 (14)	0.0493 (16)	0.0618 (15)	0.0027 (12)	0.0052 (11)	−0.0131 (13)
C2	0.078 (2)	0.0510 (19)	0.098 (2)	0.0168 (16)	−0.0056 (18)	−0.0156 (19)
C3	0.121 (3)	0.0371 (17)	0.078 (2)	0.0108 (18)	−0.020 (2)	0.0006 (15)
C4	0.105 (2)	0.0517 (18)	0.0496 (15)	−0.0264 (18)	0.0039 (15)	0.0018 (13)
C5	0.0619 (14)	0.0468 (15)	0.0438 (12)	−0.0066 (12)	0.0115 (11)	0.0000 (11)
C6	0.0452 (11)	0.0367 (12)	0.0348 (10)	−0.0035 (9)	0.0024 (8)	−0.0088 (9)
C7	0.0467 (11)	0.0398 (13)	0.0421 (11)	0.0015 (10)	0.0171 (9)	−0.0043 (10)
C8	0.0404 (10)	0.0444 (14)	0.0412 (11)	−0.0061 (10)	0.0089 (9)	0.0045 (11)
C9	0.0546 (13)	0.0496 (15)	0.0416 (11)	0.0159 (11)	0.0044 (9)	−0.0041 (11)
C10	0.0395 (10)	0.0320 (11)	0.0328 (10)	0.0023 (9)	0.0073 (8)	0.0002 (8)
C11	0.0349 (9)	0.0303 (11)	0.0326 (10)	−0.0006 (8)	0.0066 (8)	0.0007 (8)
C12	0.0548 (12)	0.0301 (11)	0.0323 (10)	0.0006 (10)	−0.0011 (9)	−0.0026 (9)
C13	0.0597 (15)	0.0450 (15)	0.0611 (15)	0.0176 (12)	−0.0013 (12)	−0.0005 (13)
C14	0.0349 (10)	0.0312 (11)	0.0323 (9)	0.0023 (8)	0.0051 (7)	0.0027 (8)
C15	0.0449 (12)	0.0502 (15)	0.0455 (12)	−0.0083 (11)	0.0206 (9)	−0.0110 (11)
C16	0.0403 (11)	0.0418 (14)	0.0507 (12)	−0.0106 (10)	0.0142 (9)	−0.0058 (11)
C17	0.0405 (10)	0.0285 (11)	0.0326 (9)	0.0027 (8)	0.0028 (7)	0.0002 (8)
C18	0.0430 (11)	0.0425 (13)	0.0348 (10)	−0.0046 (10)	0.0131 (8)	−0.0015 (10)
C19	0.0380 (10)	0.0416 (13)	0.0356 (10)	−0.0076 (9)	0.0099 (8)	−0.0011 (9)
C20	0.0684 (15)	0.0354 (13)	0.0610 (15)	0.0102 (12)	0.0003 (12)	−0.0033 (12)
N1	0.0405 (9)	0.0381 (11)	0.0339 (9)	0.0046 (8)	0.0082 (7)	−0.0027 (8)
O1	0.0568 (9)	0.0691 (13)	0.0514 (10)	−0.0151 (9)	−0.0030 (7)	−0.0109 (10)
O2	0.0398 (8)	0.0539 (11)	0.0615 (10)	0.0085 (8)	−0.0013 (7)	−0.0069 (9)
O3	0.0427 (7)	0.0306 (8)	0.0391 (7)	0.0057 (6)	0.0080 (6)	0.0016 (6)
O4	0.0711 (11)	0.0478 (11)	0.0528 (10)	−0.0009 (9)	0.0166 (8)	0.0124 (9)
O5	0.0465 (9)	0.0559 (12)	0.0697 (11)	−0.0093 (8)	0.0005 (8)	−0.0189 (9)
O6	0.0903 (13)	0.0467 (11)	0.0347 (8)	−0.0012 (10)	0.0100 (7)	−0.0013 (8)
S1	0.0475 (3)	0.0299 (2)	0.0381 (3)	0.0003 (2)	0.0016 (2)	−0.0037 (2)

Geometric parameters (Å, º) top

C1—C2	1.359 (5)	C11—C14	1.511 (3)
C1—C6	1.385 (3)	C11—H11	0.9800
C1—H1	0.9300	C12—O4	1.191 (3)
C2—C3	1.375 (5)	C12—O3	1.363 (3)
C2—H2	0.9300	C12—C13	1.492 (3)
C3—C4	1.391 (5)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.387 (4)	C13—H13C	0.9600
C4—H4	0.9300	C14—C19	1.385 (3)
C5—C6	1.379 (3)	C14—C15	1.393 (3)
C5—H5	0.9300	C15—C16	1.379 (3)
C6—C7	1.506 (3)	C15—H15	0.9300
C7—N1	1.461 (3)	C16—C17	1.383 (3)
C7—H7A	0.9700	C16—H16	0.9300
C7—H7B	0.9700	C17—C18	1.385 (3)
C8—O1	1.203 (3)	C17—S1	1.769 (2)
C8—N1	1.354 (3)	C18—C19	1.374 (3)
C8—O2	1.355 (3)	C18—H18	0.9300
C9—O2	1.421 (3)	C19—H19	0.9300
C9—C10	1.539 (3)	C20—S1	1.753 (3)
C9—H9A	0.9700	C20—H20A	0.9600
C9—H9B	0.9700	C20—H20B	0.9600
C10—N1	1.454 (3)	C20—H20C	0.9600
C10—C11	1.523 (3)	O5—S1	1.4353 (18)
C10—H10	0.9800	O6—S1	1.4346 (19)
C11—O3	1.445 (2)

C2—C1—C6	121.0 (3)	O4—C12—O3	122.3 (2)
C2—C1—H1	119.5	O4—C12—C13	126.5 (2)
C6—C1—H1	119.5	O3—C12—C13	111.1 (2)
C1—C2—C3	121.1 (3)	C12—C13—H13A	109.5
C1—C2—H2	119.5	C12—C13—H13B	109.5
C3—C2—H2	119.5	H13A—C13—H13B	109.5
C2—C3—C4	118.7 (3)	C12—C13—H13C	109.5
C2—C3—H3	120.6	H13A—C13—H13C	109.5
C4—C3—H3	120.6	H13B—C13—H13C	109.5
C5—C4—C3	120.1 (3)	C19—C14—C15	118.6 (2)
C5—C4—H4	120.0	C19—C14—C11	121.46 (18)
C3—C4—H4	120.0	C15—C14—C11	119.88 (17)
C6—C5—C4	120.4 (3)	C16—C15—C14	120.81 (19)
C6—C5—H5	119.8	C16—C15—H15	119.6
C4—C5—H5	119.8	C14—C15—H15	119.6
C5—C6—C1	118.7 (2)	C15—C16—C17	119.47 (19)
C5—C6—C7	123.6 (2)	C15—C16—H16	120.3
C1—C6—C7	117.7 (2)	C17—C16—H16	120.3
N1—C7—C6	116.12 (18)	C16—C17—C18	120.39 (19)
N1—C7—H7A	108.3	C16—C17—S1	119.40 (16)
C6—C7—H7A	108.3	C18—C17—S1	120.20 (15)
N1—C7—H7B	108.3	C19—C18—C17	119.54 (18)
C6—C7—H7B	108.3	C19—C18—H18	120.2
H7A—C7—H7B	107.4	C17—C18—H18	120.2
O1—C8—N1	127.5 (2)	C18—C19—C14	121.09 (19)
O1—C8—O2	122.1 (2)	C18—C19—H19	119.5
N1—C8—O2	110.35 (19)	C14—C19—H19	119.5
O2—C9—C10	106.0 (2)	S1—C20—H20A	109.5
O2—C9—H9A	110.5	S1—C20—H20B	109.5
C10—C9—H9A	110.5	H20A—C20—H20B	109.5
O2—C9—H9B	110.5	S1—C20—H20C	109.5
C10—C9—H9B	110.5	H20A—C20—H20C	109.5
H9A—C9—H9B	108.7	H20B—C20—H20C	109.5
N1—C10—C11	113.76 (18)	C8—N1—C10	111.57 (18)
N1—C10—C9	101.58 (17)	C8—N1—C7	119.80 (18)
C11—C10—C9	110.60 (17)	C10—N1—C7	123.54 (17)
N1—C10—H10	110.2	C8—O2—C9	110.15 (17)
C11—C10—H10	110.2	C12—O3—C11	115.21 (16)
C9—C10—H10	110.2	O6—S1—O5	118.39 (12)
O3—C11—C14	108.86 (15)	O6—S1—C20	108.39 (13)
O3—C11—C10	106.93 (14)	O5—S1—C20	109.06 (13)
C14—C11—C10	112.74 (18)	O6—S1—C17	108.20 (11)
O3—C11—H11	109.4	O5—S1—C17	107.41 (11)
C14—C11—H11	109.4	C20—S1—C17	104.53 (11)
C10—C11—H11	109.4

C6—C1—C2—C3	−0.5 (5)	C17—C18—C19—C14	1.3 (3)
C1—C2—C3—C4	0.0 (5)	C15—C14—C19—C18	1.4 (3)
C2—C3—C4—C5	0.2 (4)	C11—C14—C19—C18	−176.6 (2)
C3—C4—C5—C6	0.0 (4)	O1—C8—N1—C10	−174.6 (2)
C4—C5—C6—C1	−0.5 (3)	O2—C8—N1—C10	6.3 (2)
C4—C5—C6—C7	−177.8 (2)	O1—C8—N1—C7	−19.0 (3)
C2—C1—C6—C5	0.7 (4)	O2—C8—N1—C7	161.91 (19)
C2—C1—C6—C7	178.2 (3)	C11—C10—N1—C8	−122.93 (18)
C5—C6—C7—N1	−18.5 (3)	C9—C10—N1—C8	−4.1 (2)
C1—C6—C7—N1	164.21 (19)	C11—C10—N1—C7	82.5 (2)
O2—C9—C10—N1	0.6 (2)	C9—C10—N1—C7	−158.6 (2)
O2—C9—C10—C11	121.7 (2)	C6—C7—N1—C8	106.2 (2)
N1—C10—C11—O3	−64.6 (2)	C6—C7—N1—C10	−101.2 (2)
C9—C10—C11—O3	−178.14 (18)	O1—C8—O2—C9	175.1 (2)
N1—C10—C11—C14	175.82 (16)	N1—C8—O2—C9	−5.7 (3)
C9—C10—C11—C14	62.3 (2)	C10—C9—O2—C8	2.9 (3)
O3—C11—C14—C19	125.2 (2)	O4—C12—O3—C11	−3.3 (3)
C10—C11—C14—C19	−116.3 (2)	C13—C12—O3—C11	176.55 (18)
O3—C11—C14—C15	−52.7 (2)	C14—C11—O3—C12	−86.7 (2)
C10—C11—C14—C15	65.8 (2)	C10—C11—O3—C12	151.25 (17)
C19—C14—C15—C16	−2.5 (3)	C16—C17—S1—O6	139.88 (19)
C11—C14—C15—C16	175.5 (2)	C18—C17—S1—O6	−39.0 (2)
C14—C15—C16—C17	0.9 (4)	C16—C17—S1—O5	11.0 (2)
C15—C16—C17—C18	1.8 (3)	C18—C17—S1—O5	−167.86 (18)
C15—C16—C17—S1	−177.03 (19)	C16—C17—S1—C20	−104.8 (2)
C16—C17—C18—C19	−3.0 (3)	C18—C17—S1—C20	76.4 (2)
S1—C17—C18—C19	175.90 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O4ⁱ	0.97	2.52	3.373 (3)	147
C10—H10···O6ⁱ	0.98	2.54	3.384 (3)	144
C13—H13C···O1ⁱⁱ	0.96	2.55	3.305 (3)	135

Symmetry codes: (i) x, y, z+1; (ii) x−1, y, z−1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O4ⁱ	0.97	2.52	3.373 (3)	146.6
C10—H10···O6ⁱ	0.98	2.54	3.384 (3)	143.7
C13—H13C···O1ⁱⁱ	0.96	2.55	3.305 (3)	135.2

Symmetry codes: (i) x, y, z+1; (ii) x−1, y, z−1.

Acknowledgements

The authors thank Professor Xiang-shan Wang for his help and advice in the solution of the crystal structure.

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Jommi, G., Pagliarin, R., Chiarino, D. & Fantucci, M. (1985). Gazz. Chim. Ital. 115, 653–658. CAS Google Scholar
Li, F., Wang, Z. H., Zhao, L., Xiong, F. J., He, Q. Q. & Chen, F. E. (2011). Tetrahedron Asymmetry, 22, 1337–1341. Web of Science CSD CrossRef CAS Google Scholar
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Nagabhushan, T. L. (1981). Chem. Abstr. 94, 139433. Google Scholar
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(R)-[(R)-3-Benzyl-2-oxooxazolidin-4-yl][4-(methyl­sulfon­yl)phen­yl]methyl acetate

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organic compounds

(R)-[(R)-3-Benzyl-2-oxooxazolidin-4-yl][4-(methylsulfonyl)phenyl]methyl acetate