(1α,2β,3α,6β)-3,6-Di­chloro­cyclo­hex-4-ene-1,2-diyl di­acetate

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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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Computing details

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).

(1α,2β,3α,6β)-3,6-Dichlorocyclohex-4-ene-1,2-diyl diacetate

Crystal data

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) Å^3	Prism, colorless
Z = 4	0.45 × 0.41 × 0.38 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters not refined
wR(F^2) = 0.145	w = 1/[σ^2(Fo^2) + (0.1053P)^2 + 0.107P] where P = (Fo^2 + 2Fc^2)/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+0.001XFC^2Λ^3/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.035 (8)

Special details

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 F^{2 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 F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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···O4^v	3.374 (5)
Cl1···C8^i	3.591 (5)	C6···O4^viii	3.364 (6)
Cl2···O3	3.139 (3)	C7···O3	3.245 (5)
Cl2···O4^ii	3.314 (4)	C8···O2^vii	3.388 (7)
Cl1···H8C^i	2.6987	C8···Cl1^ix	3.591 (5)
Cl2···H1^iii	3.1100	C9···O1	3.281 (6)
O1···Cl1	3.202 (3)	C1···H8A^viii	2.9687
O1···O3	2.764 (4)	C1···H4	2.9841
O1···C9	3.281 (6)	C6···H3	3.0348
O2···C8^iv	3.388 (7)	H1···Cl2^x	3.1100
O3···C7	3.245 (5)	H2···H4	2.5659
O3···Cl2	3.139 (3)	H2···O4^v	2.7529
O3···O1	2.764 (4)	H3···O2	2.3112
O4···Cl2^v	3.314 (4)	H3···C6	3.0348
O4···C6^vi	3.364 (6)	H3···H5	2.5797
O4···C1^ii	3.086 (6)	H4···O4	2.2484
O4···C2^ii	3.374 (5)	H4···C1	2.9841
O2···H5^vii	2.6030	H4···H2	2.5659
O2···H8B^iv	2.4301	H5···H3	2.5797
O2···H3	2.3112	H5···O2^iv	2.6030
O2···H10B^iv	2.7628	H6···O4^viii	2.5210
O4···H4	2.2484	H8A···C1^vi	2.9687
O4···H6^vi	2.5210	H8B···O2^vii	2.4301
O4···H2^ii	2.7529	H8C···Cl1^ix	2.6987
C1···O4^v	3.086 (6)	H10B···O2^vii	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)

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···O4^viii	0.93	2.52	3.364 (6)	151
C8—H8B···O2^vii	0.96	2.43	3.388 (7)	174
C8—H8C···Cl1^ix	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.