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In the crystal of the title compound, mol­ecules are linked by N—H...O hydrogen bonds between the imino group and the carbonyl O atom in the ethyl ester group, forming a tape structure along the c-axis direction. The oxazolidine rings of adjacent tapes are arranged into a layer parallel to the ac plane, which is a favourable arrangement for the polymerization of the title compound in the solid state.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989014027170/is5383sup1.cif
Contains datablocks I, New_Global_Publ_Block

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989014027170/is5383Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989014027170/is5383Isup3.cml
Supplementary material

CCDC reference: 1038820

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.034
  • wR factor = 0.081
  • Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C PLAT352_ALERT_3_C Short N-H (X0.87,N1.01A) N1 - H1 ... 0.76 Ang. PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 1 Note PLAT922_ALERT_1_C wR2 in the CIF and FCF Differ by ............... -0.0026 Check PLAT923_ALERT_1_C S values in the CIF and FCF Differ by ....... -0.032 Check
Alert level G PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size .... 0.66 mm PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT432_ALERT_2_G Short Inter X...Y Contact O1 .. C2 .. 2.92 Ang. PLAT791_ALERT_4_G The Model has Chirality at C3 ............. S Verify PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) ..... 2 Report
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 4 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrystalClear (Rigaku, 2009); cell refinement: CrystalClear (Rigaku, 2009); data reduction: CrystalClear (Rigaku, 2009); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010) and Mercury (Macrae et al., 2008); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

(S)-4-[2-(Ethoxycarbonyl)ethyl]-1,3-oxazolidine-2,5-dione top
Crystal data top
C8H11NO5F(000) = 424
Mr = 201.18Dx = 1.401 Mg m3
Orthorhombic, P21212Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2 2abθ = 3.2–27.5°
a = 7.9337 (19) ŵ = 0.12 mm1
b = 20.581 (5) ÅT = 293 K
c = 5.8405 (14) ÅPrism, colorless
V = 953.7 (4) Å30.66 × 0.39 × 0.14 mm
Z = 4
Data collection top
Rigaku XtaLAB mini
diffractometer
2190 independent reflections
Radiation source: fine-focus sealed tube2042 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 6.827 pixels mm-1θmax = 27.5°, θmin = 3.2°
ω scansh = 1010
Absorption correction: multi-scan
(REQAB; Rigaku, 1998)
k = 2626
Tmin = 0.926, Tmax = 0.984l = 77
9982 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0385P)2 + 0.167P]
where P = (Fo2 + 2Fc2)/3
2190 reflections(Δ/σ)max = 0.010
131 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.16 e Å3
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
xyzUiso*/Ueq
O10.02731 (16)0.77067 (6)0.0480 (2)0.0538 (4)
O20.10460 (14)0.72562 (4)0.25649 (18)0.0385 (3)
O30.27691 (18)0.70878 (5)0.5536 (2)0.0548 (4)
O40.19733 (14)0.94889 (5)0.93375 (19)0.0417 (3)
O50.26952 (18)1.03085 (5)0.7069 (2)0.0539 (4)
N10.15491 (17)0.82887 (6)0.1795 (2)0.0344 (3)
C10.06782 (19)0.77729 (7)0.1092 (3)0.0355 (3)
C20.22322 (19)0.74470 (6)0.4126 (3)0.0340 (3)
C30.26475 (17)0.81536 (6)0.3704 (2)0.0283 (3)
C40.23203 (19)0.85660 (6)0.5828 (3)0.0318 (3)
C50.2829 (3)0.92684 (7)0.5461 (3)0.0425 (4)
C60.24451 (18)0.96852 (6)0.7513 (3)0.0336 (3)
C70.2257 (3)1.07707 (7)0.8886 (4)0.0504 (5)
C80.3640 (3)1.08564 (9)1.0556 (4)0.0575 (5)
H10.156 (3)0.8596 (10)0.108 (4)0.0517*
H30.38270.81970.32310.0339*
H4A0.11320.85470.62100.0381*
H4B0.29500.83890.71080.0381*
H5A0.40270.92880.51390.0509*
H5B0.22340.94390.41400.0509*
H7A0.12611.06170.96820.0604*
H7B0.19901.11880.82040.0604*
H8A0.46231.10170.97820.0689*
H8B0.38951.04461.12590.0689*
H8C0.33011.11611.17110.0689*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0582 (7)0.0549 (7)0.0482 (7)0.0087 (6)0.0192 (6)0.0092 (6)
O20.0425 (6)0.0261 (4)0.0470 (6)0.0067 (4)0.0017 (5)0.0028 (5)
O30.0817 (9)0.0355 (5)0.0473 (6)0.0005 (6)0.0118 (7)0.0098 (5)
O40.0598 (7)0.0274 (4)0.0380 (6)0.0052 (5)0.0094 (6)0.0030 (4)
O50.0899 (9)0.0257 (5)0.0461 (6)0.0118 (6)0.0003 (7)0.0003 (5)
N10.0486 (7)0.0267 (5)0.0280 (5)0.0060 (5)0.0048 (5)0.0024 (5)
C10.0387 (7)0.0328 (7)0.0349 (7)0.0035 (6)0.0014 (6)0.0044 (6)
C20.0431 (7)0.0275 (6)0.0313 (7)0.0004 (6)0.0049 (7)0.0027 (6)
C30.0323 (6)0.0269 (6)0.0256 (6)0.0043 (5)0.0016 (5)0.0021 (5)
C40.0411 (7)0.0278 (6)0.0264 (6)0.0037 (5)0.0040 (6)0.0032 (5)
C50.0633 (10)0.0333 (7)0.0308 (7)0.0130 (7)0.0052 (8)0.0035 (6)
C60.0402 (7)0.0245 (6)0.0361 (7)0.0054 (5)0.0046 (6)0.0002 (5)
C70.0536 (9)0.0243 (6)0.0732 (11)0.0023 (7)0.0051 (9)0.0090 (7)
C80.0606 (10)0.0450 (9)0.0668 (12)0.0006 (8)0.0007 (10)0.0164 (9)
Geometric parameters (Å, º) top
O1—C11.1964 (18)C4—C51.5159 (18)
O2—C21.3677 (18)C4—H4A0.9700
O2—C11.3985 (18)C4—H4B0.9700
O3—C21.1861 (17)C5—C61.505 (2)
O4—C61.1997 (18)C5—H5A0.9700
O5—C61.3237 (15)C5—H5B0.9700
O5—C71.467 (2)C7—C81.478 (3)
N1—C11.3314 (18)C7—H7A0.9700
N1—C31.4423 (18)C7—H7B0.9700
N1—H10.76 (2)C8—H8A0.9600
C2—C31.5113 (17)C8—H8B0.9600
C3—C41.5251 (17)C8—H8C0.9600
C3—H30.9800
C2—O2—C1109.58 (10)H4A—C4—H4B107.9
C6—O5—C7116.82 (14)C6—C5—C4112.17 (12)
C1—N1—C3113.46 (12)C6—C5—H5A109.2
C1—N1—H1119.9 (15)C4—C5—H5A109.2
C3—N1—H1125.7 (15)C6—C5—H5B109.2
O1—C1—N1130.91 (15)C4—C5—H5B109.2
O1—C1—O2121.12 (13)H5A—C5—H5B107.9
N1—C1—O2107.97 (12)O4—C6—O5123.17 (14)
O3—C2—O2122.09 (13)O4—C6—C5125.34 (12)
O3—C2—C3129.38 (14)O5—C6—C5111.49 (13)
O2—C2—C3108.53 (11)O5—C7—C8112.25 (14)
N1—C3—C2100.35 (11)O5—C7—H7A109.2
N1—C3—C4114.75 (11)C8—C7—H7A109.2
C2—C3—C4111.48 (11)O5—C7—H7B109.2
N1—C3—H3110.0C8—C7—H7B109.2
C2—C3—H3110.0H7A—C7—H7B107.9
C4—C3—H3110.0C7—C8—H8A109.5
C5—C4—C3111.76 (11)C7—C8—H8B109.5
C5—C4—H4A109.3H8A—C8—H8B109.5
C3—C4—H4A109.3C7—C8—H8C109.5
C5—C4—H4B109.3H8A—C8—H8C109.5
C3—C4—H4B109.3H8B—C8—H8C109.5
C3—N1—C1—O1176.31 (16)O3—C2—C3—C457.2 (2)
C3—N1—C1—O23.49 (17)O2—C2—C3—C4122.05 (12)
C2—O2—C1—O1176.53 (14)N1—C3—C4—C570.08 (16)
C2—O2—C1—N13.30 (16)C2—C3—C4—C5176.72 (13)
C1—O2—C2—O3178.76 (14)C3—C4—C5—C6177.65 (13)
C1—O2—C2—C31.89 (15)C7—O5—C6—O44.1 (2)
C1—N1—C3—C22.23 (15)C7—O5—C6—C5176.04 (14)
C1—N1—C3—C4121.83 (14)C4—C5—C6—O48.0 (2)
O3—C2—C3—N1179.18 (16)C4—C5—C6—O5172.05 (13)
O2—C2—C3—N10.11 (14)C6—O5—C7—C884.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.76 (2)2.13 (2)2.8766 (17)170 (2)
Symmetry code: (i) x, y, z1.
 

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