(4S)-4-[(R)-Chloro-(4-nitro-phen-yl)meth-yl]-1,3-oxazolidin-2-one.

In the title compound, C10H9ClN2O4, the oxazolidinone ring adopts a near-planar conformation, with mean and maximum deviations of 0.0204 (8) and 0.0328 (8) Å, respectively. The nitro group is twisted slightly from the plane of the benzene ring, making a dihedral angle of 6.79 (3)°. The dihedral angle between the mean oxazolidinone plane and the benzene ring is 56.21 (3)°. In the crystal, N-H⋯O hydrogen bonds and N-O⋯π inter-actions [O⋯centroid distances = 3.478 (1) and 3.238 (1) Å] dominate the packing, forming infinite zigzag chains along the b-axis direction. Neighbouring chains are linked together through C-H⋯O and C-H⋯Cl inter-actions. The absolute configuration of the two stereogenic centres was determined using the anomalous dispersion of the Cl atom.

Related literature

For the biological activity of oxazolidinone derivatives, see: Michalska et al. (2012 ▶); Mathur et al. (2013 ▶); Jindal et al. (2013 ▶). For related structures, see: Bach et al. (2001 ▶); Tsui et al. (2013 ▶). For detailed of the synthesis, see: Madesclaire et al. (2013 ▶).

Experimental

Crystal data

C10H9ClN2O4

M = 256.64

Monoclinic,

a = 7.2372 (1) Å

b = 6.6726 (1) Å

c = 11.7126 (2) Å

β = 106.715 (1)°

V = 541.71 (1) Å3

Z = 2

Mo Kα radiation

μ = 0.36 mm−1

T = 296 K

0.52 × 0.49 × 0.34 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2012 ▶) T min = 0.915, T max = 1.000

12895 measured reflections

6114 independent reflections

5384 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.098

S = 1.06

6114 reflections

158 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.44 e Å−3

Absolute structure: Flack (1983 ▶), 2348 Friedel pairs

Flack parameter: −0.03 (3)

Data collection: APEX2 (Bruker, 2012 ▶); cell refinement: SAINT (Bruker, 2012 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813010398/kp2451sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010398/kp2451Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813010398/kp2451Isup3.cml

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

C10H9ClN2O4	F(000) = 264
Mr = 256.64	Dx = 1.573 Mg m−3
Monoclinic, P21	Melting point: 414 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 7.2372 (1) Å	Cell parameters from 6817 reflections
b = 6.6726 (1) Å	θ = 4.0–39.2°
c = 11.7126 (2) Å	µ = 0.36 mm−1
β = 106.715 (1)°	T = 296 K
V = 541.71 (1) Å3	Block prism, colourless
Z = 2	0.52 × 0.49 × 0.34 mm

Bruker APEXII CCD diffractometer	6114 independent reflections
Radiation source: fine-focus sealed tube	5384 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
φ and ω scans	θmax = 41.1°, θmin = 4.2°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −11→13
Tmin = 0.915, Tmax = 1.000	k = −12→10
12895 measured reflections	l = −21→21

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0548P)2 + 0.0254P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
6114 reflections	Δρmax = 0.33 e Å−3
158 parameters	Δρmin = −0.44 e Å−3
1 restraint	Absolute structure: Flack (1983), 2348 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.03 (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
O1	−0.27342 (14)	1.09892 (14)	0.00860 (7)	0.04046 (18)
C2	−0.09939 (17)	1.16003 (16)	0.07729 (9)	0.03409 (18)
N3	−0.04803 (15)	1.04959 (14)	0.17795 (9)	0.0379 (2)
H3	0.035 (3)	1.073 (4)	0.234 (2)	0.064 (7)*
C4	−0.18727 (13)	0.89934 (14)	0.18369 (8)	0.02872 (15)
H4	−0.2438	0.9293	0.2484	0.034*
C5	−0.33823 (17)	0.9297 (2)	0.06159 (11)	0.0423 (2)
H5A	−0.3460	0.8116	0.0121	0.051*
H5B	−0.4646	0.9553	0.0716	0.051*
C6	−0.09944 (12)	0.68917 (13)	0.19899 (7)	0.02377 (12)
H6	−0.0574	0.6564	0.1288	0.029*
C7	0.07040 (11)	0.67131 (13)	0.30890 (7)	0.02336 (12)
C8	0.04894 (13)	0.68896 (17)	0.42314 (7)	0.02948 (16)
H8	−0.0736	0.7054	0.4323	0.035*
C9	0.20770 (14)	0.68227 (17)	0.52297 (7)	0.03020 (16)
H9	0.1936	0.6931	0.5992	0.036*
C10	0.38832 (12)	0.65896 (14)	0.50598 (7)	0.02706 (14)
C11	0.41443 (13)	0.64207 (18)	0.39412 (9)	0.03193 (17)
H11	0.5374	0.6270	0.3855	0.038*
C12	0.25405 (13)	0.64796 (18)	0.29494 (8)	0.02991 (16)
H12	0.2691	0.6363	0.2190	0.036*
N13	0.55799 (13)	0.64956 (14)	0.61094 (8)	0.03406 (16)
O14	0.53442 (16)	0.6452 (3)	0.70939 (8)	0.0556 (3)
O15	0.71821 (13)	0.6472 (2)	0.59423 (9)	0.0488 (2)
O16	−0.0129 (2)	1.29556 (17)	0.04888 (10)	0.0528 (3)
Cl17	−0.28820 (3)	0.51760 (4)	0.20713 (2)	0.03492 (6)

	U11	U22	U33	U12	U13	U23
O1	0.0460 (4)	0.0391 (4)	0.0291 (3)	0.0070 (3)	−0.0005 (3)	0.0078 (3)
C2	0.0433 (5)	0.0272 (4)	0.0324 (4)	0.0033 (4)	0.0119 (4)	0.0008 (3)
N3	0.0380 (4)	0.0299 (4)	0.0352 (4)	−0.0064 (3)	−0.0062 (3)	0.0051 (3)
C4	0.0271 (4)	0.0286 (3)	0.0258 (3)	0.0025 (3)	0.0002 (3)	0.0024 (3)
C5	0.0337 (5)	0.0426 (5)	0.0383 (5)	−0.0012 (4)	−0.0092 (4)	0.0089 (4)
C6	0.0232 (3)	0.0272 (3)	0.0201 (3)	0.0001 (2)	0.0049 (2)	0.0002 (2)
C7	0.0223 (3)	0.0262 (3)	0.0209 (3)	0.0023 (2)	0.0051 (2)	0.0020 (2)
C8	0.0229 (3)	0.0433 (5)	0.0221 (3)	0.0036 (3)	0.0063 (2)	0.0017 (3)
C9	0.0285 (4)	0.0399 (4)	0.0210 (3)	0.0030 (3)	0.0052 (3)	0.0024 (3)
C10	0.0248 (3)	0.0277 (3)	0.0250 (3)	0.0037 (3)	0.0013 (2)	0.0025 (3)
C11	0.0225 (3)	0.0415 (5)	0.0311 (4)	0.0062 (3)	0.0067 (3)	0.0010 (3)
C12	0.0256 (3)	0.0409 (4)	0.0239 (3)	0.0057 (3)	0.0083 (2)	0.0008 (3)
N13	0.0301 (3)	0.0315 (3)	0.0330 (4)	0.0043 (3)	−0.0029 (3)	0.0024 (3)
O14	0.0484 (5)	0.0801 (8)	0.0293 (4)	0.0045 (5)	−0.0032 (3)	0.0063 (5)
O15	0.0270 (3)	0.0631 (6)	0.0483 (5)	0.0074 (4)	−0.0018 (3)	0.0020 (5)
O16	0.0723 (7)	0.0370 (4)	0.0576 (6)	−0.0051 (4)	0.0321 (5)	0.0057 (4)
Cl17	0.03212 (10)	0.03645 (11)	0.03473 (10)	−0.00833 (9)	0.00727 (7)	−0.00087 (8)

O1—C2	1.3480 (15)	C7—C12	1.3938 (12)
O1—C5	1.4310 (16)	C7—C8	1.3956 (11)
C2—O16	1.2004 (15)	C8—C9	1.3844 (13)
C2—N3	1.3487 (14)	C8—H8	0.9300
N3—C4	1.4367 (14)	C9—C10	1.3863 (13)
N3—H3	0.77 (2)	C9—H9	0.9300
C4—C6	1.5288 (12)	C10—C11	1.3811 (13)
C4—C5	1.5431 (13)	C10—N13	1.4679 (11)
C4—H4	0.9800	C11—C12	1.3866 (13)
C5—H5A	0.9700	C11—H11	0.9300
C5—H5B	0.9700	C12—H12	0.9300
C6—C7	1.5073 (11)	N13—O14	1.2136 (14)
C6—Cl17	1.8058 (9)	N13—O15	1.2303 (13)
C6—H6	0.9800
C2—O1—C5	110.26 (8)	C4—C6—H6	109.0
O16—C2—O1	122.33 (11)	Cl17—C6—H6	109.0
O16—C2—N3	128.27 (12)	C12—C7—C8	119.65 (7)
O1—C2—N3	109.38 (9)	C12—C7—C6	118.66 (7)
C2—N3—C4	113.67 (9)	C8—C7—C6	121.59 (7)
C2—N3—H3	126.1 (18)	C9—C8—C7	120.85 (8)
C4—N3—H3	119.1 (18)	C9—C8—H8	119.6
N3—C4—C6	111.84 (8)	C7—C8—H8	119.6
N3—C4—C5	100.62 (8)	C8—C9—C10	118.05 (8)
C6—C4—C5	112.87 (8)	C8—C9—H9	121.0
N3—C4—H4	110.4	C10—C9—H9	121.0
C6—C4—H4	110.4	C11—C10—C9	122.49 (8)
C5—C4—H4	110.4	C11—C10—N13	118.76 (8)
O1—C5—C4	105.81 (9)	C9—C10—N13	118.74 (8)
O1—C5—H5A	110.6	C10—C11—C12	118.85 (8)
C4—C5—H5A	110.6	C10—C11—H11	120.6
O1—C5—H5B	110.6	C12—C11—H11	120.6
C4—C5—H5B	110.6	C11—C12—C7	120.10 (8)
H5A—C5—H5B	108.7	C11—C12—H12	119.9
C7—C6—C4	112.46 (7)	C7—C12—H12	119.9
C7—C6—Cl17	110.38 (6)	O14—N13—O15	123.18 (10)
C4—C6—Cl17	107.00 (6)	O14—N13—C10	118.97 (9)
C7—C6—H6	109.0	O15—N13—C10	117.84 (9)
C5—O1—C2—O16	177.34 (12)	Cl17—C6—C7—C8	−53.58 (10)
C5—O1—C2—N3	−3.94 (14)	C12—C7—C8—C9	−0.42 (15)
O16—C2—N3—C4	179.45 (12)	C6—C7—C8—C9	−176.72 (9)
O1—C2—N3—C4	0.83 (14)	C7—C8—C9—C10	0.44 (15)
C2—N3—C4—C6	122.37 (10)	C8—C9—C10—C11	−0.12 (16)
C2—N3—C4—C5	2.29 (13)	C8—C9—C10—N13	−179.40 (9)
C2—O1—C5—C4	5.25 (13)	C9—C10—C11—C12	−0.22 (17)
N3—C4—C5—O1	−4.35 (12)	N13—C10—C11—C12	179.06 (10)
C6—C4—C5—O1	−123.69 (10)	C10—C11—C12—C7	0.23 (17)
N3—C4—C6—C7	57.76 (10)	C8—C7—C12—C11	0.08 (16)
C5—C4—C6—C7	170.37 (8)	C6—C7—C12—C11	176.48 (10)
N3—C4—C6—Cl17	179.12 (6)	C11—C10—N13—O14	−173.10 (13)
C5—C4—C6—Cl17	−68.26 (9)	C9—C10—N13—O14	6.21 (16)
C4—C6—C7—C12	−110.50 (10)	C11—C10—N13—O15	7.17 (15)
Cl17—C6—C7—C12	130.09 (8)	C9—C10—N13—O15	−173.52 (11)
C4—C6—C7—C8	65.84 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O15i	0.77 (2)	2.32 (2)	3.095 (1)	179 (2)
C6—H6···O16ii	0.98	2.46	3.309 (2)	145
C11—H11···Cl17iii	0.93	2.83	3.582 (1)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O15i	0.77 (2)	2.32 (2)	3.095 (1)	179 (2)
C6—H6⋯O16ii	0.98	2.46	3.309 (2)	145
C11—H11⋯Cl17iii	0.93	2.83	3.582 (1)	139

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