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The crystal structure of the title compound, C8H13ClO3, has been determined at 262 (2) K following in-situ growth from the liquid.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801017512/cv6069sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801017512/cv6069Isup2.hkl
Contains datablock I

CCDC reference: 176032

Key indicators

  • Single-crystal X-ray study
  • T = 262 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.040
  • wR factor = 0.093
  • Data-to-parameter ratio = 15.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.04 From the CIF: _reflns_number_total 1704 Count of symmetry unique reflns 1065 Completeness (_total/calc) 160.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 639 Fraction of Friedel pairs measured 0.600 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.

Comment top

This work forms part of a continuing study devoted to improving the techniques for determining the crystal structures of substances which are liquids at room temperature [see, for example, Davies & Bond (2001)]. The structure of (-)-(4S)-1-chloro-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propan-2-one, (2), is reported here.

Experimental top

The sample was obtained from methyl ester (1), prepared using the method of Steel & Thomas (1997). Treatment of (1) with in situ generated chloromethyllithium (Barluenga et al., 1995)) at 195 K in dichloromethane afforded the title compound (2) in 94% yield. The crystal was grown in a 0.3 mm glass capillary tube at 278 K. This temperature is less than 1 K below the observed melting point of the solid in the tube and allowed solid and liquid to exist together in the tube for a period of at least several hours. With the axis of the capillary parallel to the ϕ axis and HORIZONTAL on the instrument (a Nonius KappaCCD diffractometer equipped with an Oxford Cryosystems Cryostream cooler), the crystal was obtained overnight from the very slow movement of the solid/liquid interface (the tube remaining stationary during the period of crystal growth). Attempts to grow a suitable crystal by moving a plug of solid material up and down the tube using a method reported earlier (Davies & Bond, 2001) were unsuccessful, but one of the best of these attempts was used as the starting point for the stationary-tube method which produced the data crystal.

Refinement top

H atoms were placed geometrically and refined using the usual riding model. The absolute configuration was determined satisfactorily from the X-ray data [Flack (1983) parameter = -0.2 (1), number of Friedel pairs = 649], confirming the known configuration of the starting material.

Computing details top

Data collection: COLLECT (Nonius BV, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1993).

Figures top
[Figure 1] Fig. 1. The molecular structure and atom-labeling scheme of (2). Displacement ellipsoids are drawn at the 50% probability level.
(I) top
Crystal data top
C8H13ClO3Dx = 1.283 Mg m3
Mr = 192.63Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 3592 reflections
a = 5.3067 (2) Åθ = 1.0–25.0°
b = 9.3552 (6) ŵ = 0.35 mm1
c = 20.0955 (12) ÅT = 262 K
V = 997.65 (10) Å3Cylinder, colourless
Z = 40.13 mm (radius)
F(000) = 408
Data collection top
Nonius KappaCCD
diffractometer
1385 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.090
Horizonally mounted graphite crystal monochromatorθmax = 25.0°, θmin = 2.0°
Detector resolution: 9 pixels mm-1h = 56
fine–slice ω/ϕ scansk = 811
5899 measured reflectionsl = 2322
1704 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040 w = 1/[σ2(Fo2) + (0.0247P)2 + 0.1484P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.093(Δ/σ)max < 0.001
S = 1.14Δρmax = 0.16 e Å3
1701 reflectionsΔρmin = 0.18 e Å3
113 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.019 (5)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.17 (12)
Crystal data top
C8H13ClO3V = 997.65 (10) Å3
Mr = 192.63Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 5.3067 (2) ŵ = 0.35 mm1
b = 9.3552 (6) ÅT = 262 K
c = 20.0955 (12) Å0.13 mm (radius)
Data collection top
Nonius KappaCCD
diffractometer
1385 reflections with I > 2σ(I)
5899 measured reflectionsRint = 0.090
1704 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.093Δρmax = 0.16 e Å3
S = 1.14Δρmin = 0.18 e Å3
1701 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
113 parametersAbsolute structure parameter: 0.17 (12)
0 restraints
Special details top

Experimental. Grown in -situ at 278 °·K. in a 0.4 mm Lindemann tube. Collimator diameter 0.25 mm. Number of Friedel pairs = 649

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 on F2 for ALL reflections except for 3 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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
Cl10.4719 (2)0.25154 (10)0.35191 (4)0.0846 (3)
O10.6613 (3)0.3621 (2)0.47839 (9)0.0578 (5)
O20.2840 (3)0.6077 (2)0.62195 (10)0.0658 (6)
O30.5937 (3)0.7612 (2)0.59906 (9)0.0643 (5)
C10.3066 (5)0.3688 (3)0.40549 (13)0.0580 (7)
H1A0.2732 (5)0.4575 (3)0.38207 (13)0.070*
H1B0.1457 (5)0.3262 (3)0.41692 (13)0.070*
C20.4490 (5)0.4017 (2)0.46865 (12)0.0466 (6)
C30.3003 (5)0.4904 (3)0.51726 (14)0.0540 (6)
H3A0.1521 (5)0.4372 (3)0.53086 (14)0.065*
H3B0.2436 (5)0.5768 (3)0.49517 (14)0.065*
C40.4493 (5)0.5309 (3)0.57829 (13)0.0517 (7)
H40.5119 (5)0.4447 (3)0.60049 (13)0.062*
C50.6644 (5)0.6338 (3)0.5662 (2)0.0669 (9)
H5A0.8203 (5)0.5965 (3)0.5845 (2)0.080*
H5B0.6871 (5)0.6506 (3)0.5190 (2)0.080*
C60.4203 (4)0.7228 (3)0.64975 (12)0.0503 (6)
C70.5548 (8)0.6790 (5)0.7116 (2)0.1027 (14)
H7A0.676 (3)0.6062 (19)0.7012 (3)0.114 (5)*
H7B0.4354 (10)0.643 (2)0.7432 (5)0.114 (5)*
H7C0.640 (4)0.7603 (8)0.7303 (6)0.114 (5)*
C80.2398 (6)0.8439 (3)0.6609 (2)0.0746 (9)
H8A0.156 (3)0.8666 (17)0.6199 (3)0.114 (5)*
H8B0.3306 (8)0.9261 (8)0.6764 (11)0.114 (5)*
H8C0.117 (3)0.8164 (10)0.6936 (9)0.114 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0960 (6)0.1030 (7)0.0549 (4)0.0109 (6)0.0013 (4)0.0155 (5)
O10.0469 (11)0.0578 (11)0.0688 (12)0.0086 (9)0.0015 (9)0.0052 (10)
O20.0491 (11)0.0598 (11)0.0884 (14)0.0100 (9)0.0215 (10)0.0225 (10)
O30.0639 (11)0.0602 (11)0.0688 (12)0.0146 (11)0.0161 (8)0.0167 (10)
C10.058 (2)0.053 (2)0.062 (2)0.0006 (13)0.0026 (13)0.0047 (14)
C20.046 (2)0.0359 (12)0.058 (2)0.0030 (11)0.0001 (11)0.0059 (11)
C30.0461 (14)0.0448 (14)0.071 (2)0.0022 (11)0.0035 (12)0.0020 (14)
C40.0476 (15)0.0455 (13)0.062 (2)0.0040 (12)0.0076 (12)0.0026 (13)
C50.048 (2)0.070 (2)0.083 (2)0.0049 (14)0.0111 (14)0.024 (2)
C60.0442 (13)0.0558 (15)0.0510 (14)0.0026 (12)0.0005 (11)0.0032 (13)
C70.094 (3)0.154 (4)0.061 (2)0.029 (3)0.010 (2)0.007 (2)
C80.080 (2)0.062 (2)0.081 (2)0.010 (2)0.005 (2)0.011 (2)
Geometric parameters (Å, º) top
Cl1—C11.770 (3)C4—C51.513 (4)
O1—C21.202 (3)C4—H40.98
O2—C61.412 (3)C5—H5A0.97
O2—C41.433 (3)C5—H5B0.97
O3—C51.413 (3)C6—C71.491 (4)
O3—C61.419 (3)C6—C81.500 (4)
C1—C21.509 (4)C7—H7A0.96
C1—H1A0.97C7—H7B0.96
C1—H1B0.97C7—H7C0.96
C2—C31.505 (4)C8—H8A0.96
C3—C41.508 (4)C8—H8B0.96
C3—H3A0.97C8—H8C0.96
C3—H3B0.97
C6—O2—C4108.1 (2)O3—C5—H5A110.7 (2)
C5—O3—C6107.1 (2)C4—C5—H5A110.7 (2)
C2—C1—Cl1113.0 (2)O3—C5—H5B110.7 (2)
C2—C1—H1A108.99 (14)C4—C5—H5B110.7 (2)
Cl1—C1—H1A108.99 (9)H5A—C5—H5B108.8
C2—C1—H1B108.99 (15)O2—C6—O3104.0 (2)
Cl1—C1—H1B108.99 (10)O2—C6—C7111.4 (3)
H1A—C1—H1B107.8O3—C6—C7110.9 (2)
O1—C2—C3123.7 (2)O2—C6—C8108.0 (2)
O1—C2—C1122.9 (2)O3—C6—C8109.3 (2)
C3—C2—C1113.3 (2)C7—C6—C8112.8 (3)
C2—C3—C4113.1 (2)C6—C7—H7A109.5 (2)
C2—C3—H3A108.97 (13)C6—C7—H7B109.5 (2)
C4—C3—H3A108.97 (14)H7A—C7—H7B109.5
C2—C3—H3B108.97 (13)C6—C7—H7C109.5 (2)
C4—C3—H3B108.97 (14)H7A—C7—H7C109.5
H3A—C3—H3B107.8H7B—C7—H7C109.5
O2—C4—C3107.6 (2)C6—C8—H8A109.5 (2)
O2—C4—C5103.9 (2)C6—C8—H8B109.5 (2)
C3—C4—C5115.2 (2)H8A—C8—H8B109.5
O2—C4—H4109.94 (14)C6—C8—H8C109.5 (2)
C3—C4—H4109.94 (14)H8A—C8—H8C109.5
C5—C4—H4109.9 (2)H8B—C8—H8C109.5
O3—C5—C4105.2 (2)
Cl1—C1—C2—O16.2 (3)O2—C4—C5—O34.5 (3)
Cl1—C1—C2—C3174.7 (2)C3—C4—C5—O3113.0 (2)
O1—C2—C3—C42.8 (3)C4—O2—C6—O331.7 (3)
C1—C2—C3—C4176.3 (2)C4—O2—C6—C787.8 (3)
C6—O2—C4—C3139.4 (2)C4—O2—C6—C8147.8 (2)
C6—O2—C4—C516.8 (3)C5—O3—C6—O234.7 (3)
C2—C3—C4—O2176.8 (2)C5—O3—C6—C785.2 (3)
C2—C3—C4—C567.8 (3)C5—O3—C6—C8149.7 (2)
C6—O3—C5—C424.1 (3)

Experimental details

Crystal data
Chemical formulaC8H13ClO3
Mr192.63
Crystal system, space groupOrthorhombic, P212121
Temperature (K)262
a, b, c (Å)5.3067 (2), 9.3552 (6), 20.0955 (12)
V3)997.65 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.35
Crystal size (mm)0.13 (radius)
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
5899, 1704, 1385
Rint0.090
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.093, 1.14
No. of reflections1701
No. of parameters113
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.18
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter0.17 (12)

Computer programs: COLLECT (Nonius BV, 1997-2000), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK, SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), XP (Sheldrick, 1993).

 

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