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We present here a second positional isomer of C10H12Cl2O4. The crystal was found to be inversion twinned. The cyclohexene ring adopts a distorted half-chair conformation.
Supporting information
CCDC reference: 251628
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.049
- wR factor = 0.145
- Data-to-parameter ratio = 9.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ?
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors for C9
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
Alert level G
REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may
be needed to determine absolute structure
From the CIF: _diffrn_reflns_theta_max 26.00
From the CIF: _reflns_number_total 1448
Count of symmetry unique reflns 1449
Completeness (_total/calc) 99.93%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 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
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
(1
α,2
β,3
α,6
β)-3,6-Dichlorocyclohex-4-ene-1,2-diyl diacetate
top
Crystal data top
C10H12Cl2O4 | F(000) = 552 |
Mr = 267.10 | Dx = 1.416 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1448 reflections |
a = 7.8525 (7) Å | θ = 2.0–26.3° |
b = 7.8036 (5) Å | µ = 0.51 mm−1 |
c = 20.4482 (12) Å | T = 293 K |
V = 1253.02 (16) Å3 | Prism, colorless |
Z = 4 | 0.45 × 0.41 × 0.38 mm |
Data collection top
Stoe IPDS-II diffractometer | 1248 reflections with I > 2σ(I) |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | Rint = 0.056 |
Plane graphite monochromator | θmax = 26.0°, θmin = 2.0° |
Detector resolution: 6.67 pixels mm-1 | h = −9→9 |
ω scans | k = −9→9 |
17519 measured reflections | l = −25→25 |
1448 independent reflections | |
Refinement top
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)] = 0.049 | H-atom parameters not refined |
wR(F2) = 0.145 | w = 1/[σ2(Fo2) + (0.1053P)2 + 0.107P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
1448 reflections | Δρmax = 0.36 e Å−3 |
147 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXL97, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.035 (8) |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those 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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.05486 (15) | 0.5113 (2) | 0.66763 (7) | 0.0969 (5) | |
Cl2 | 0.73662 (17) | 0.50901 (15) | 0.51826 (6) | 0.0909 (4) | |
O1 | 0.3024 (4) | 0.8352 (3) | 0.65342 (11) | 0.0635 (8) | |
O2 | 0.3746 (6) | 0.8253 (5) | 0.75947 (13) | 0.0962 (13) | |
O3 | 0.6427 (4) | 0.7740 (3) | 0.62795 (12) | 0.0652 (8) | |
O4 | 0.6169 (5) | 0.9804 (4) | 0.55193 (17) | 0.0934 (11) | |
C1 | 0.2839 (7) | 0.4052 (6) | 0.5775 (2) | 0.0783 (14) | |
C2 | 0.2187 (6) | 0.5656 (5) | 0.6074 (2) | 0.0693 (12) | |
C3 | 0.3602 (5) | 0.6637 (5) | 0.64187 (16) | 0.0586 (11) | |
C4 | 0.5128 (5) | 0.6737 (5) | 0.59649 (17) | 0.0602 (11) | |
C5 | 0.5811 (5) | 0.4966 (5) | 0.58382 (18) | 0.0648 (11) | |
C6 | 0.4457 (7) | 0.3737 (6) | 0.5664 (2) | 0.0750 (14) | |
C7 | 0.3197 (6) | 0.9036 (5) | 0.71368 (18) | 0.0646 (11) | |
C8 | 0.2723 (7) | 1.0865 (5) | 0.7131 (2) | 0.0733 (14) | |
C9 | 0.6861 (6) | 0.9241 (5) | 0.5998 (2) | 0.0693 (12) | |
C10 | 0.8280 (7) | 1.0050 (8) | 0.6366 (3) | 0.1013 (19) | |
H1 | 0.20510 | 0.32160 | 0.56580 | 0.0940* | |
H2 | 0.16880 | 0.63810 | 0.57330 | 0.0830* | |
H3 | 0.39110 | 0.60760 | 0.68310 | 0.0710* | |
H4 | 0.47960 | 0.72770 | 0.55510 | 0.0720* | |
H5 | 0.63830 | 0.45590 | 0.62350 | 0.0780* | |
H6 | 0.47600 | 0.27040 | 0.54700 | 0.0900* | |
H8A | 0.23230 | 1.11750 | 0.67040 | 0.1100* | |
H8B | 0.37000 | 1.15480 | 0.72410 | 0.1100* | |
H8C | 0.18380 | 1.10630 | 0.74460 | 0.1100* | |
H10A | 0.85960 | 0.93280 | 0.67260 | 0.1520* | |
H10B | 0.79200 | 1.11460 | 0.65280 | 0.1520* | |
H10C | 0.92400 | 1.01990 | 0.60810 | 0.1520* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0736 (6) | 0.1190 (11) | 0.0981 (8) | −0.0078 (8) | 0.0160 (6) | −0.0064 (7) |
Cl2 | 0.1080 (9) | 0.0730 (6) | 0.0916 (8) | 0.0047 (7) | 0.0431 (6) | −0.0096 (5) |
O1 | 0.0752 (15) | 0.0653 (14) | 0.0501 (12) | 0.0125 (13) | −0.0059 (11) | −0.0061 (10) |
O2 | 0.139 (3) | 0.095 (2) | 0.0547 (14) | 0.030 (2) | −0.0164 (18) | −0.0056 (14) |
O3 | 0.0705 (15) | 0.0647 (14) | 0.0603 (14) | −0.0007 (13) | −0.0079 (12) | −0.0004 (12) |
O4 | 0.112 (2) | 0.0773 (19) | 0.091 (2) | −0.020 (2) | −0.013 (2) | 0.0255 (17) |
C1 | 0.101 (3) | 0.062 (2) | 0.072 (2) | −0.010 (3) | −0.003 (2) | −0.0065 (18) |
C2 | 0.071 (2) | 0.071 (2) | 0.066 (2) | −0.0002 (19) | −0.0092 (19) | −0.0020 (18) |
C3 | 0.067 (2) | 0.0600 (19) | 0.0488 (16) | 0.0094 (18) | −0.0008 (15) | 0.0000 (15) |
C4 | 0.073 (2) | 0.058 (2) | 0.0495 (16) | 0.0035 (18) | −0.0010 (16) | −0.0009 (14) |
C5 | 0.078 (2) | 0.0583 (19) | 0.0581 (19) | 0.009 (2) | 0.0063 (16) | −0.0015 (17) |
C6 | 0.101 (3) | 0.056 (2) | 0.068 (2) | 0.001 (2) | 0.010 (2) | −0.0050 (18) |
C7 | 0.070 (2) | 0.068 (2) | 0.0558 (18) | 0.0058 (19) | −0.0014 (17) | −0.0089 (17) |
C8 | 0.084 (3) | 0.063 (2) | 0.073 (2) | 0.001 (2) | 0.001 (2) | −0.0143 (18) |
C9 | 0.073 (2) | 0.063 (2) | 0.072 (2) | 0.000 (2) | 0.005 (2) | 0.0008 (19) |
C10 | 0.092 (3) | 0.096 (3) | 0.116 (4) | −0.020 (4) | −0.012 (3) | −0.015 (3) |
Geometric parameters (Å, º) top
Cl1—C2 | 1.831 (5) | C7—C8 | 1.475 (6) |
Cl2—C5 | 1.816 (4) | C9—C10 | 1.485 (7) |
O1—C3 | 1.433 (5) | C1—H1 | 0.9304 |
O1—C7 | 1.350 (4) | C2—H2 | 0.9797 |
O2—C7 | 1.198 (5) | C3—H3 | 0.9805 |
O3—C4 | 1.438 (5) | C4—H4 | 0.9807 |
O3—C9 | 1.349 (5) | C5—H5 | 0.9803 |
O4—C9 | 1.203 (5) | C6—H6 | 0.9294 |
C1—C2 | 1.484 (6) | C8—H8A | 0.9589 |
C1—C6 | 1.314 (8) | C8—H8B | 0.9609 |
C2—C3 | 1.522 (6) | C8—H8C | 0.9601 |
C3—C4 | 1.518 (5) | C10—H10A | 0.9596 |
C4—C5 | 1.505 (6) | C10—H10B | 0.9598 |
C5—C6 | 1.476 (6) | C10—H10C | 0.9599 |
| | | |
Cl1···O1 | 3.202 (3) | C2···O4v | 3.374 (5) |
Cl1···C8i | 3.591 (5) | C6···O4viii | 3.364 (6) |
Cl2···O3 | 3.139 (3) | C7···O3 | 3.245 (5) |
Cl2···O4ii | 3.314 (4) | C8···O2vii | 3.388 (7) |
Cl1···H8Ci | 2.6987 | C8···Cl1ix | 3.591 (5) |
Cl2···H1iii | 3.1100 | C9···O1 | 3.281 (6) |
O1···Cl1 | 3.202 (3) | C1···H8Aviii | 2.9687 |
O1···O3 | 2.764 (4) | C1···H4 | 2.9841 |
O1···C9 | 3.281 (6) | C6···H3 | 3.0348 |
O2···C8iv | 3.388 (7) | H1···Cl2x | 3.1100 |
O3···C7 | 3.245 (5) | H2···H4 | 2.5659 |
O3···Cl2 | 3.139 (3) | H2···O4v | 2.7529 |
O3···O1 | 2.764 (4) | H3···O2 | 2.3112 |
O4···Cl2v | 3.314 (4) | H3···C6 | 3.0348 |
O4···C6vi | 3.364 (6) | H3···H5 | 2.5797 |
O4···C1ii | 3.086 (6) | H4···O4 | 2.2484 |
O4···C2ii | 3.374 (5) | H4···C1 | 2.9841 |
O2···H5vii | 2.6030 | H4···H2 | 2.5659 |
O2···H8Biv | 2.4301 | H5···H3 | 2.5797 |
O2···H3 | 2.3112 | H5···O2iv | 2.6030 |
O2···H10Biv | 2.7628 | H6···O4viii | 2.5210 |
O4···H4 | 2.2484 | H8A···C1vi | 2.9687 |
O4···H6vi | 2.5210 | H8B···O2vii | 2.4301 |
O4···H2ii | 2.7529 | H8C···Cl1ix | 2.6987 |
C1···O4v | 3.086 (6) | H10B···O2vii | 2.7628 |
| | | |
C3—O1—C7 | 119.2 (3) | C1—C2—H2 | 109.38 |
C4—O3—C9 | 117.5 (3) | C3—C2—H2 | 109.33 |
C2—C1—C6 | 124.2 (5) | O1—C3—H3 | 110.72 |
Cl1—C2—C1 | 108.9 (3) | C2—C3—H3 | 110.75 |
Cl1—C2—C3 | 108.5 (3) | C4—C3—H3 | 110.69 |
C1—C2—C3 | 111.3 (4) | O3—C4—H4 | 109.93 |
O1—C3—C2 | 108.4 (3) | C3—C4—H4 | 109.87 |
O1—C3—C4 | 107.6 (3) | C5—C4—H4 | 109.92 |
C2—C3—C4 | 108.6 (3) | Cl2—C5—H5 | 108.67 |
O3—C4—C3 | 108.3 (3) | C4—C5—H5 | 108.56 |
O3—C4—C5 | 108.9 (3) | C6—C5—H5 | 108.63 |
C3—C4—C5 | 109.8 (3) | C1—C6—H6 | 118.92 |
Cl2—C5—C4 | 108.5 (3) | C5—C6—H6 | 118.84 |
Cl2—C5—C6 | 109.9 (3) | C7—C8—H8A | 109.52 |
C4—C5—C6 | 112.4 (4) | C7—C8—H8B | 109.47 |
C1—C6—C5 | 122.2 (4) | C7—C8—H8C | 109.45 |
O1—C7—O2 | 123.2 (4) | H8A—C8—H8B | 109.56 |
O1—C7—C8 | 110.5 (3) | H8A—C8—H8C | 109.46 |
O2—C7—C8 | 126.2 (4) | H8B—C8—H8C | 109.37 |
O3—C9—O4 | 123.4 (4) | C9—C10—H10A | 109.45 |
O3—C9—C10 | 110.0 (4) | C9—C10—H10B | 109.43 |
O4—C9—C10 | 126.6 (4) | C9—C10—H10C | 109.45 |
C2—C1—H1 | 117.89 | H10A—C10—H10B | 109.55 |
C6—C1—H1 | 117.87 | H10A—C10—H10C | 109.50 |
Cl1—C2—H2 | 109.35 | H10B—C10—H10C | 109.45 |
| | | |
C7—O1—C3—C2 | 130.8 (4) | Cl1—C2—C3—O1 | −76.0 (3) |
C7—O1—C3—C4 | −111.9 (4) | C1—C2—C3—O1 | 164.1 (3) |
C3—O1—C7—C8 | 173.1 (4) | O1—C3—C4—C5 | 178.8 (3) |
C3—O1—C7—O2 | −3.5 (7) | C2—C3—C4—O3 | 177.1 (3) |
C9—O3—C4—C5 | 125.3 (3) | C2—C3—C4—C5 | −64.1 (4) |
C4—O3—C9—C10 | −176.8 (4) | O1—C3—C4—O3 | 60.0 (4) |
C4—O3—C9—O4 | 3.3 (6) | C3—C4—C5—C6 | 47.8 (4) |
C9—O3—C4—C3 | −115.3 (4) | O3—C4—C5—Cl2 | −71.9 (3) |
C6—C1—C2—C3 | −17.2 (6) | C3—C4—C5—Cl2 | 169.6 (2) |
C2—C1—C6—C5 | 0.9 (7) | O3—C4—C5—C6 | 166.3 (3) |
C6—C1—C2—Cl1 | −136.8 (4) | C4—C5—C6—C1 | −16.4 (6) |
Cl1—C2—C3—C4 | 167.3 (3) | Cl2—C5—C6—C1 | −137.5 (4) |
C1—C2—C3—C4 | 47.5 (4) | | |
Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) x+1/2, −y+3/2, −z+1; (iii) x+1/2, −y+1/2, −z+1; (iv) −x+1, y−1/2, −z+3/2; (v) x−1/2, −y+3/2, −z+1; (vi) x, y+1, z; (vii) −x+1, y+1/2, −z+3/2; (viii) x, y−1, z; (ix) −x, y+1/2, −z+3/2; (x) x−1/2, −y+1/2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2 | 0.98 | 2.31 | 2.718 (5) | 104 |
C4—H4···O4 | 0.98 | 2.25 | 2.688 (5) | 106 |
C6—H6···O4viii | 0.93 | 2.52 | 3.364 (6) | 151 |
C8—H8B···O2vii | 0.96 | 2.43 | 3.388 (7) | 174 |
C8—H8C···Cl1ix | 0.96 | 2.70 | 3.591 (5) | 155 |
Symmetry codes: (vii) −x+1, y+1/2, −z+3/2; (viii) x, y−1, z; (ix) −x, y+1/2, −z+3/2. |
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