2,2-Dichloro-1-(2-phenyl-1,3-oxazolidin-3-yl)ethanone.

Abstract

In the title mol-ecule, C(11)H(11)Cl(2)NO(2), the oxazolidine ring is in an envelope conformation with the O atom forming the flap; the other four essentially planar ring atoms (r.m.s. deviation = 0.012 Å) form a dihedral angle of 91.1 (3)° with the phenyl ring. In the crystal structure, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds, forming one-dimensional chains.

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2,2-Dichloro-1-(2-phenyl-1,3-oxazolidin-
3-yl)ethanone
Fei Ye, Ying Fu* and Shuang Zhao
College of Science, Northeast Agricultural University, Harbin 150030, People’s
Republic of China
Correspondence e-mail: fuying@neau.edu.cn
Received 11 January 2010; accepted 19 January 2010
Key indicators: single-crystal X-ray study; T = 298 K; mean ?(C–C) = 0.003 A ˚;
R factor = 0.040; wR factor = 0.110; data-to-parameter ratio = 19.6.
In the title molecule, C11H11Cl2NO2, the oxazolidine ring is in
an envelope conformation with the O atom forming the flap;
the other four essentially planar ring atoms (r.m.s. deviation =
0.012 A˚) form a dihedral angle of 91.1 (3)?with the phenyl
ring. In the crystal structure, molecules are linked by weak
intermolecular C—H???O hydrogen bonds, forming one-
dimensional chains.
Related literature
For general background to substituted oxazolidines see:
Agami et al. (2004); Guirado et al. (2003); Tararov et al. (2003).
For the bioactivity of related compounds, see: Hatzios et al.
(2004); Daniele et al. (2007). For details of the synthesis, see:
Fu et al. (2009).
Experimental
Crystal data
C11H11Cl2NO2
Mr= 260.11
Orthorhombic, Pccn
a = 19.1775 (13) A˚
b = 10.6165 (7) A˚
c = 11.3723 (8) A˚
V = 2315.4 (3) A˚3
Z = 8
Mo K? radiation
? = 0.54 mm?1
T = 298 K
0.46 ? 0.38 ? 0.20 mm
Data collection
Bruker SMART CCD
diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
Tmin= 0.780, Tmax= 0.897
16860 measured reflections
2846 independent reflections
2323 reflections with I > 2?(I)
Rint= 0.022
Refinement
R[F2> 2?(F2)] = 0.040
wR(F2) = 0.110
S = 1.04
2846 reflections
145 parameters
H-atom parameters constrained
??max= 0.41 e A˚?3
??min= ?0.29 e A˚?3
Table 1
Hydrogen-bond geometry (A˚,?).
D—H???A
C11—H11???O2i
Symmetry code: (i) ?x þ 1;y ?1
D—HH???AD???AD—H???A
0.982.403.312 (2)156
2;?z þ3
2.
Data collection: SMART (Bruker, 1998); cell refinement: SAINT
(Bruker, 1998); data reduction: SAINT; program(s) used to solve
structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine
structure:SHELXL97(Sheldrick,
SHELXTL (Sheldrick, 2008); software used to prepare material for
publication: SHELXTL.
2008);molecular graphics:
We thanksthe Heilongjiang Province Foundation for Young
Scholar (QC2009C44), the China Postdoctoral Science Foun-
dation (20080430951), the Heilongjiang Province Postdoctoral
Science Foundation (LBH-Z07012) and the Northeast Agri-
cultural University Doctoral Foundation for generously
supporting this study.
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: LH2978).
References
Agami, C. & Couty, F. (2004). Eur. J. Org. Chem. 69, 677–685.
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin,
USA.
Daniele, D. B., Luciano, S. & Luca, E. (2007). Phytochemistry, 68, 2614–2618.
Fu, Y., Fu, H. G., Ye, F., Mao, J. D. & Wen, X. T. (2009). Synth. Commun. 39,
2454–2463.
Guirado, A., Andreu, R. & Galvez, J. (2003). Tetrahedron Lett. 44, 3809–3841.
Hatzios, K. K. (2004). Weed Sci. 52, 454–467.
Sheldrick, G. M. (1996). SADABS. University of Go ¨ttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Tararov, V. I., Kadyrov, R., Monsees, A., Riermeier, T. H. & Boerner, A.
(2003). Adv. Synth. Catal. 345, 239–245.
organic compounds
Acta Cryst. (2010). E66, o445doi:10.1107/S1600536810002461Ye et al.
o445
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368

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supplementary materials

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supplementary materials
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Acta Cryst. (2010). E66, o445 [ doi:10.1107/S1600536810002461 ]
2,2-Dichloro-1-(2-phenyl-1,3-oxazolidin-3-yl)ethanone
F. Ye, Y. Fu and S. Zhao
Comment
Substituted oxazolidines are important synthetic targets due to their biological activity (Agami et al., 2004), pharmacological
activity and their extensive use as chiral auxiliaries for the synthesis of many chiral compounds (Guirado et al., 2003;
Tararov et al. 2003). Dichloroacetemide compounds have been shown to act as herbicide safeners (Hatzios, 2004; Daniele
et al., 2007). As part of our ongoing investigations of oxazolidine derivatives we prepared the title compound and its crystal
structure is reported herein.
The molecular structure of the title compound is shown in Fig.1. In the crystal structure, molecules are linked by weak
intermolecular C—H···O hydrogen bonds to form one-dimensional chains (Fig. 2).
Experimental
The title compound was prepared by a slightly modified literature procedure (Fu et al., 2009).
Ethanolamine (4.1 g, 0.067 mol) and 7.1g (0.067mol) of benzaldehyde were mixed with 25mL of benzene. The reaction
mixture was stirred for 1h at 306-308K. Then, the mixture was heated to reflux and water was evaporated, followed by
cooling to 273K and 7.5 mL of 33% sodium hydroxide solution was added. 11.8 g (0.08mol) of dichloroacetyl chloride was
added dropwise with stirring, keeping the temperature at 273-277K. Stirring was continued for 1.5h. The mixture was rinsed
with water until the pH=7. The organic phase was dried over anhydrous magnesium sulfate and the benzene was removed
under vacuum. The crude product was recrystallized with ethyl acetate and light petroleum, white crystals wre obtained.
The yield was 58.2%. m.p. 374-377K.
The single-crystal suitable for X-ray structural analysis was obtained by slow evaporation of a solution of the title com-
pound in petroleum ether and ethyl acetate at room temperature.
Refinement
All H atoms were initially located in a difference Fourier map. The C—H atoms were then constrained to an ideal geometry,
with C-H = 0.93 - 0.98Å and Uiso(H) = 1.2Ueq(C).
Figures
Fig. 1. The molecular structure of the title compound, with the atom-labelling
scheme.Displacement ellipsoids are drawn at the 30% probability level.

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Fig. 2. Part of the crystal structure of the title compound showing C-H···O hydrogen bonds as
dashed lines.
2,2-Dichloro-1-(2-phenyl-1,3-oxazolidin-3-yl)ethanone
Crystal data
C11H11Cl2NO2
F(000) = 1072.0
Dx = 1.492 Mg m−3
Dm = 1.492 Mg m−3
Dm measured by not measured
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 5877 reflections
θ = 2.8–27.9°
µ = 0.54 mm−1
T = 298 K
Mr = 260.11
Orthorhombic, Pccn
Hall symbol: -P 2ab 2ac
a = 19.1775 (13) Å
b = 10.6165 (7) Å
c = 11.3723 (8) Å
V = 2315.4 (3) Å3
Z = 8
Block, colourless
0.46 × 0.38 × 0.20 mm
Data collection
Bruker SMART CCD
diffractometer
Radiation source: fine-focus sealed tube
graphite
φ and ω scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
Tmin = 0.780, Tmax = 0.897
16860 measured reflections
2846 independent reflections
2323 reflections with I > 2σ(I)
Rint = 0.022
θmax = 28.3°, θmin = 2.8°
h = −25→25
k = −14→14
l = −15→15
Refinement
Refinement on F2
Primary atom site location: structure-invariant direct
methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring
sites
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.040
wR(F2) = 0.110
H-atom parameters constrained
S = 1.04
w = 1/[σ2(Fo2) + (0.0473P)2 + 1.2513P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
2846 reflections

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145 parameters
Δρmax = 0.41 e Å−3
Δρmin = −0.29 e Å−3
0 restraints
Special details
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 mat-
rix. 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, convention-
al 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)
x
0.43189 (3)
0.38622 (3)
0.54978 (8)
0.60625 (8)
0.46001 (9)
0.4904
0.49952 (9)
0.48479 (8)
0.56836 (10)
0.5882
0.5283
0.65059 (10)
0.58735 (10)
0.5557
0.67948 (11)
0.6588
0.62234 (13)
0.6187
0.6692
0.73902 (12)
0.7579
0.76916 (14)
0.8087
0.74266 (15)
0.7644
0.68205 (13)
0.6635
y
0.78273 (5)
0.67345 (6)
0.77484 (13)
0.77362 (14)
0.72103 (16)
0.6483
0.82044 (15)
0.93204 (12)
0.64244 (17)
0.6034
0.5940
0.91874 (17)
0.85716 (17)
0.9221
0.8764 (2)
0.8094
0.65601 (19)
0.5872
0.6571
0.9323 (2)
0.9027
1.0306 (3)
1.0684
1.0743 (2)
1.1408
1.0194 (2)
1.0503
z
0.61104 (4)
0.83020 (5)
0.88700 (13)
1.06154 (12)
0.74626 (16)
0.7323
0.81777 (15)
0.81157 (14)
0.90877 (18)
0.8393
0.9347
0.91330 (18)
0.96905 (16)
0.9992
0.8089 (2)
0.7696
1.0063 (2)
1.0620
0.9741
0.7616 (3)
0.6915
0.8190 (3)
0.7873
0.9217 (3)
0.9602
0.9706 (3)
1.0404
Uiso*/Ueq
0.05385 (16)
0.06457 (19)
0.0370 (3)
0.0555 (4)
0.0398 (4)
0.048*
0.0372 (4)
0.0554 (4)
0.0468 (4)
0.056*
0.056*
0.0469 (4)
0.0431 (4)
0.052*
0.0549 (5)
0.066*
0.0593 (6)
0.071*
0.071*
0.0722 (7)
0.087*
0.0880 (10)
0.106*
0.0859 (10)
0.103*
0.0687 (7)
0.082*
Cl1
Cl2
N1
O1
C11
H11
C10
O2
C9
H9A
H9B
C5
C7
H7
C6
H6
C8
H8A
H8B
C1
H1
C2
H2
C3
H3
C4
H4