Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801017512/cv6069sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801017512/cv6069Isup2.hkl |
CCDC reference: 176032
Key indicators
- Single-crystal X-ray study
- T = 262 K
- Mean (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.
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.
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.
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).
Fig. 1. The molecular structure and atom-labeling scheme of (2). Displacement ellipsoids are drawn at the 50% probability level. |
C8H13ClO3 | Dx = 1.283 Mg m−3 |
Mr = 192.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 3592 reflections |
a = 5.3067 (2) Å | θ = 1.0–25.0° |
b = 9.3552 (6) Å | µ = 0.35 mm−1 |
c = 20.0955 (12) Å | T = 262 K |
V = 997.65 (10) Å3 | Cylinder, colourless |
Z = 4 | 0.13 mm (radius) |
F(000) = 408 |
Nonius KappaCCD diffractometer | 1385 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.090 |
Horizonally mounted graphite crystal monochromator | θmax = 25.0°, θmin = 2.0° |
Detector resolution: 9 pixels mm-1 | h = −5→6 |
fine–slice ω/ϕ scans | k = −8→11 |
5899 measured reflections | l = −23→22 |
1704 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-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 = 1.14 | Δρmax = 0.16 e Å−3 |
1701 reflections | Δρmin = −0.18 e Å−3 |
113 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.019 (5) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.17 (12) |
C8H13ClO3 | V = 997.65 (10) Å3 |
Mr = 192.63 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.3067 (2) Å | µ = 0.35 mm−1 |
b = 9.3552 (6) Å | T = 262 K |
c = 20.0955 (12) Å | 0.13 mm (radius) |
Nonius KappaCCD diffractometer | 1385 reflections with I > 2σ(I) |
5899 measured reflections | Rint = 0.090 |
1704 independent reflections |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.093 | Δρmax = 0.16 e Å−3 |
S = 1.14 | Δρmin = −0.18 e Å−3 |
1701 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
113 parameters | Absolute structure parameter: −0.17 (12) |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.4719 (2) | 0.25154 (10) | 0.35191 (4) | 0.0846 (3) | |
O1 | 0.6613 (3) | 0.3621 (2) | 0.47839 (9) | 0.0578 (5) | |
O2 | 0.2840 (3) | 0.6077 (2) | 0.62195 (10) | 0.0658 (6) | |
O3 | 0.5937 (3) | 0.7612 (2) | 0.59906 (9) | 0.0643 (5) | |
C1 | 0.3066 (5) | 0.3688 (3) | 0.40549 (13) | 0.0580 (7) | |
H1A | 0.2732 (5) | 0.4575 (3) | 0.38207 (13) | 0.070* | |
H1B | 0.1457 (5) | 0.3262 (3) | 0.41692 (13) | 0.070* | |
C2 | 0.4490 (5) | 0.4017 (2) | 0.46865 (12) | 0.0466 (6) | |
C3 | 0.3003 (5) | 0.4904 (3) | 0.51726 (14) | 0.0540 (6) | |
H3A | 0.1521 (5) | 0.4372 (3) | 0.53086 (14) | 0.065* | |
H3B | 0.2436 (5) | 0.5768 (3) | 0.49517 (14) | 0.065* | |
C4 | 0.4493 (5) | 0.5309 (3) | 0.57829 (13) | 0.0517 (7) | |
H4 | 0.5119 (5) | 0.4447 (3) | 0.60049 (13) | 0.062* | |
C5 | 0.6644 (5) | 0.6338 (3) | 0.5662 (2) | 0.0669 (9) | |
H5A | 0.8203 (5) | 0.5965 (3) | 0.5845 (2) | 0.080* | |
H5B | 0.6871 (5) | 0.6506 (3) | 0.5190 (2) | 0.080* | |
C6 | 0.4203 (4) | 0.7228 (3) | 0.64975 (12) | 0.0503 (6) | |
C7 | 0.5548 (8) | 0.6790 (5) | 0.7116 (2) | 0.1027 (14) | |
H7A | 0.676 (3) | 0.6062 (19) | 0.7012 (3) | 0.114 (5)* | |
H7B | 0.4354 (10) | 0.643 (2) | 0.7432 (5) | 0.114 (5)* | |
H7C | 0.640 (4) | 0.7603 (8) | 0.7303 (6) | 0.114 (5)* | |
C8 | 0.2398 (6) | 0.8439 (3) | 0.6609 (2) | 0.0746 (9) | |
H8A | 0.156 (3) | 0.8666 (17) | 0.6199 (3) | 0.114 (5)* | |
H8B | 0.3306 (8) | 0.9261 (8) | 0.6764 (11) | 0.114 (5)* | |
H8C | 0.117 (3) | 0.8164 (10) | 0.6936 (9) | 0.114 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0960 (6) | 0.1030 (7) | 0.0549 (4) | 0.0109 (6) | 0.0013 (4) | −0.0155 (5) |
O1 | 0.0469 (11) | 0.0578 (11) | 0.0688 (12) | 0.0086 (9) | −0.0015 (9) | −0.0052 (10) |
O2 | 0.0491 (11) | 0.0598 (11) | 0.0884 (14) | −0.0100 (9) | 0.0215 (10) | −0.0225 (10) |
O3 | 0.0639 (11) | 0.0602 (11) | 0.0688 (12) | −0.0146 (11) | 0.0161 (8) | −0.0167 (10) |
C1 | 0.058 (2) | 0.053 (2) | 0.062 (2) | 0.0006 (13) | −0.0026 (13) | 0.0047 (14) |
C2 | 0.046 (2) | 0.0359 (12) | 0.058 (2) | −0.0030 (11) | 0.0001 (11) | 0.0059 (11) |
C3 | 0.0461 (14) | 0.0448 (14) | 0.071 (2) | 0.0022 (11) | 0.0035 (12) | −0.0020 (14) |
C4 | 0.0476 (15) | 0.0455 (13) | 0.062 (2) | 0.0040 (12) | 0.0076 (12) | −0.0026 (13) |
C5 | 0.048 (2) | 0.070 (2) | 0.083 (2) | −0.0049 (14) | 0.0111 (14) | −0.024 (2) |
C6 | 0.0442 (13) | 0.0558 (15) | 0.0510 (14) | −0.0026 (12) | −0.0005 (11) | −0.0032 (13) |
C7 | 0.094 (3) | 0.154 (4) | 0.061 (2) | 0.029 (3) | −0.010 (2) | 0.007 (2) |
C8 | 0.080 (2) | 0.062 (2) | 0.081 (2) | 0.010 (2) | 0.005 (2) | −0.011 (2) |
Cl1—C1 | 1.770 (3) | C4—C5 | 1.513 (4) |
O1—C2 | 1.202 (3) | C4—H4 | 0.98 |
O2—C6 | 1.412 (3) | C5—H5A | 0.97 |
O2—C4 | 1.433 (3) | C5—H5B | 0.97 |
O3—C5 | 1.413 (3) | C6—C7 | 1.491 (4) |
O3—C6 | 1.419 (3) | C6—C8 | 1.500 (4) |
C1—C2 | 1.509 (4) | C7—H7A | 0.96 |
C1—H1A | 0.97 | C7—H7B | 0.96 |
C1—H1B | 0.97 | C7—H7C | 0.96 |
C2—C3 | 1.505 (4) | C8—H8A | 0.96 |
C3—C4 | 1.508 (4) | C8—H8B | 0.96 |
C3—H3A | 0.97 | C8—H8C | 0.96 |
C3—H3B | 0.97 | ||
C6—O2—C4 | 108.1 (2) | O3—C5—H5A | 110.7 (2) |
C5—O3—C6 | 107.1 (2) | C4—C5—H5A | 110.7 (2) |
C2—C1—Cl1 | 113.0 (2) | O3—C5—H5B | 110.7 (2) |
C2—C1—H1A | 108.99 (14) | C4—C5—H5B | 110.7 (2) |
Cl1—C1—H1A | 108.99 (9) | H5A—C5—H5B | 108.8 |
C2—C1—H1B | 108.99 (15) | O2—C6—O3 | 104.0 (2) |
Cl1—C1—H1B | 108.99 (10) | O2—C6—C7 | 111.4 (3) |
H1A—C1—H1B | 107.8 | O3—C6—C7 | 110.9 (2) |
O1—C2—C3 | 123.7 (2) | O2—C6—C8 | 108.0 (2) |
O1—C2—C1 | 122.9 (2) | O3—C6—C8 | 109.3 (2) |
C3—C2—C1 | 113.3 (2) | C7—C6—C8 | 112.8 (3) |
C2—C3—C4 | 113.1 (2) | C6—C7—H7A | 109.5 (2) |
C2—C3—H3A | 108.97 (13) | C6—C7—H7B | 109.5 (2) |
C4—C3—H3A | 108.97 (14) | H7A—C7—H7B | 109.5 |
C2—C3—H3B | 108.97 (13) | C6—C7—H7C | 109.5 (2) |
C4—C3—H3B | 108.97 (14) | H7A—C7—H7C | 109.5 |
H3A—C3—H3B | 107.8 | H7B—C7—H7C | 109.5 |
O2—C4—C3 | 107.6 (2) | C6—C8—H8A | 109.5 (2) |
O2—C4—C5 | 103.9 (2) | C6—C8—H8B | 109.5 (2) |
C3—C4—C5 | 115.2 (2) | H8A—C8—H8B | 109.5 |
O2—C4—H4 | 109.94 (14) | C6—C8—H8C | 109.5 (2) |
C3—C4—H4 | 109.94 (14) | H8A—C8—H8C | 109.5 |
C5—C4—H4 | 109.9 (2) | H8B—C8—H8C | 109.5 |
O3—C5—C4 | 105.2 (2) | ||
Cl1—C1—C2—O1 | 6.2 (3) | O2—C4—C5—O3 | −4.5 (3) |
Cl1—C1—C2—C3 | −174.7 (2) | C3—C4—C5—O3 | 113.0 (2) |
O1—C2—C3—C4 | 2.8 (3) | C4—O2—C6—O3 | 31.7 (3) |
C1—C2—C3—C4 | −176.3 (2) | C4—O2—C6—C7 | −87.8 (3) |
C6—O2—C4—C3 | −139.4 (2) | C4—O2—C6—C8 | 147.8 (2) |
C6—O2—C4—C5 | −16.8 (3) | C5—O3—C6—O2 | −34.7 (3) |
C2—C3—C4—O2 | −176.8 (2) | C5—O3—C6—C7 | 85.2 (3) |
C2—C3—C4—C5 | 67.8 (3) | C5—O3—C6—C8 | −149.7 (2) |
C6—O3—C5—C4 | 24.1 (3) |
Experimental details
Crystal data | |
Chemical formula | C8H13ClO3 |
Mr | 192.63 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 262 |
a, b, c (Å) | 5.3067 (2), 9.3552 (6), 20.0955 (12) |
V (Å3) | 997.65 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.35 |
Crystal size (mm) | 0.13 (radius) |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5899, 1704, 1385 |
Rint | 0.090 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.093, 1.14 |
No. of reflections | 1701 |
No. of parameters | 113 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.18 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | −0.17 (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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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.