(1α,2β,5β,6α)-5,6-Di­chloro-3-cyclo­hexene-1,2-diyl di­acetate

The reaction of endo-cis-7-oxabi­cyclo­[2.2.1]­hept-5-ene-2,3-diol with BCl₃ followed by acetyl­ation with acetyl chloride gives di­chloro­conduritol derivatives. The crystal structure of the title compound, C₁₀H₁₂Cl₂O₄, has been investigated. The cyclo­hexene ring adopts a distorted half-chair conformation.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.049
• wR factor = 0.149
• Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ......       3.25 Sigma
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.65 mm
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C7

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   2 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,5β,6α)-5,6-Dichloro-3-cyclohexene-1,2-diyl diacetate

Crystal data

C10H12Cl2O4	F(000) = 552
Mr = 267.10	Dx = 1.477 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2616 reflections
a = 7.4270 (6) Å	θ = 1.9–26.9°
b = 21.6166 (15) Å	µ = 0.54 mm^−1
c = 8.3108 (7) Å	T = 293 K
β = 115.768 (6)°	Block, colorless
V = 1201.59 (17) Å^3	0.65 × 0.52 × 0.36 mm
Z = 4

Data collection

Stoe IPDS-II diffractometer	2616 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1839 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.046
Detector resolution: 6.67 pixels mm^-1	θmax = 27.2°, θmin = 1.9°
ω scans	h = −9→9
Absorption correction: integration STOE X-RED32 (Stoe & Cie, 2002)	k = −27→27
Tmin = 0.722, Tmax = 0.831	l = −10→10
18742 measured 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) = 0.149	w = 1/[σ^2(Fo^2) + (0.0871P)^2 + 0.1417P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
2616 reflections	Δρmax = 0.48 e Å^−3
146 parameters	Δρmin = −0.44 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: 0.013 (4)

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	0.72207 (15)	0.76760 (3)	0.51088 (11)	0.0805 (3)
Cl2	1.05511 (12)	0.71194 (4)	0.37556 (12)	0.0818 (3)
O1	0.4676 (3)	0.58777 (9)	0.2177 (2)	0.0626 (6)
O2	0.7102 (2)	0.64255 (8)	0.6792 (2)	0.0531 (5)
O3	0.2557 (4)	0.52125 (15)	0.2401 (3)	0.1114 (10)
O4	0.4317 (3)	0.60864 (16)	0.6886 (3)	0.1034 (12)
C1	0.9501 (4)	0.60256 (12)	0.4573 (3)	0.0533 (8)
C2	0.8013 (4)	0.56402 (11)	0.4210 (3)	0.0536 (8)
C3	0.6022 (3)	0.58314 (12)	0.4073 (3)	0.0517 (7)
C4	0.6072 (3)	0.64680 (12)	0.4873 (3)	0.0487 (7)
C5	0.7253 (3)	0.69114 (11)	0.4301 (3)	0.0468 (7)
C6	0.9394 (3)	0.66933 (11)	0.4924 (3)	0.0494 (7)
C7	0.3057 (4)	0.55273 (11)	0.1500 (3)	0.0507 (7)
C8	0.1974 (4)	0.55978 (14)	−0.0476 (3)	0.0651 (9)
C9	0.6024 (4)	0.62398 (16)	0.7657 (3)	0.0630 (9)
C10	0.7224 (5)	0.62635 (17)	0.9614 (3)	0.0705 (10)
H1	1.06890	0.58720	0.46130	0.0640*
H2	0.82090	0.52260	0.40280	0.0640*
H3	0.55250	0.55230	0.46460	0.0620*
H4	0.47100	0.66230	0.45050	0.0580*
H5	0.66270	0.69260	0.29930	0.0560*
H6	1.01340	0.67700	0.62090	0.0590*
H8A	0.26970	0.58770	−0.08790	0.0980*
H8B	0.06610	0.57600	−0.07880	0.0980*
H8C	0.18660	0.52020	−0.10340	0.0980*
H10A	0.85500	0.64050	0.98820	0.1060*
H10B	0.72930	0.58580	1.01080	0.1060*
H10C	0.66110	0.65430	1.01250	0.1060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.1077 (7)	0.0521 (4)	0.0773 (5)	0.0102 (4)	0.0360 (4)	−0.0059 (3)
Cl2	0.0708 (5)	0.0882 (6)	0.0930 (6)	−0.0196 (4)	0.0418 (4)	0.0177 (4)
O1	0.0572 (10)	0.0783 (12)	0.0362 (8)	−0.0318 (9)	0.0053 (7)	0.0069 (8)
O2	0.0460 (9)	0.0767 (11)	0.0351 (7)	−0.0060 (7)	0.0162 (6)	0.0022 (7)
O3	0.0997 (18)	0.146 (2)	0.0624 (13)	−0.0742 (18)	0.0109 (12)	0.0155 (14)
O4	0.0559 (13)	0.198 (3)	0.0573 (12)	−0.0270 (14)	0.0256 (10)	0.0125 (15)
C1	0.0474 (13)	0.0598 (15)	0.0499 (12)	0.0076 (10)	0.0186 (10)	0.0051 (10)
C2	0.0613 (15)	0.0439 (12)	0.0473 (12)	0.0018 (10)	0.0159 (11)	0.0007 (9)
C3	0.0503 (13)	0.0593 (14)	0.0351 (10)	−0.0165 (10)	0.0090 (9)	0.0049 (9)
C4	0.0406 (11)	0.0684 (15)	0.0345 (10)	−0.0005 (10)	0.0138 (9)	0.0044 (9)
C5	0.0518 (12)	0.0439 (11)	0.0406 (11)	0.0003 (9)	0.0163 (9)	0.0020 (8)
C6	0.0453 (12)	0.0544 (13)	0.0445 (11)	−0.0094 (10)	0.0158 (10)	0.0024 (9)
C7	0.0484 (13)	0.0537 (13)	0.0455 (12)	−0.0131 (10)	0.0163 (10)	−0.0032 (10)
C8	0.0591 (15)	0.0781 (19)	0.0448 (13)	−0.0174 (13)	0.0101 (11)	−0.0077 (12)
C9	0.0541 (15)	0.094 (2)	0.0466 (13)	−0.0035 (13)	0.0273 (12)	0.0045 (12)
C10	0.0777 (18)	0.094 (2)	0.0435 (13)	−0.0025 (15)	0.0297 (13)	0.0047 (13)

Geometric parameters (Å, º)

Cl1—C5	1.788 (2)	C7—C8	1.490 (3)
Cl2—C6	1.804 (3)	C9—C10	1.477 (3)
O1—C3	1.457 (3)	C1—H1	0.9297
O1—C7	1.322 (4)	C2—H2	0.9300
O2—C4	1.441 (3)	C3—H3	0.9799
O2—C9	1.349 (3)	C4—H4	0.9798
O3—C7	1.185 (4)	C5—H5	0.9795
O4—C9	1.192 (4)	C6—H6	0.9797
C1—C2	1.310 (4)	C8—H8A	0.9598
C1—C6	1.482 (4)	C8—H8B	0.9598
C2—C3	1.491 (4)	C8—H8C	0.9598
C3—C4	1.522 (4)	C10—H10A	0.9604
C4—C5	1.509 (3)	C10—H10B	0.9598
C5—C6	1.518 (3)	C10—H10C	0.9596
Cl1···Cl2	3.3540 (15)	C9···H3	2.8273
Cl1···O2	3.0625 (19)	C10···H8B^v	2.9247
Cl2···Cl1	3.3540 (15)	H1···O4^i	2.5726
Cl2···H4^i	3.0672	H3···O3	2.2836
Cl2···H10C^ii	3.0816	H3···O4	2.6844
O2···Cl1	3.0625 (19)	H3···C9	2.8273
O2···C1	3.191 (3)	H3···O3^iii	2.7460
O3···C9^iii	3.319 (5)	H3···H3^iii	2.5428
O4···C3	3.154 (3)	H4···Cl2^iv	3.0672
O4···C1^iv	3.245 (4)	H4···O4	2.4184
O1···H5	2.6154	H5···O1	2.6154
O2···H8B^v	2.9119	H5···C2	2.9838
O2···H6	2.6094	H5···H10C^vii	2.5184
O3···H3^iii	2.7460	H6···O2	2.6094
O3···H3	2.2836	H8A···O4^vii	2.6544
O4···H1^iv	2.5726	H8B···O2^viii	2.9119
O4···H3	2.6844	H8B···C10^viii	2.9247
O4···H4	2.4184	H8B···H10A^viii	2.3391
O4···H8A^vi	2.6544	H8C···H10B^iii	2.4114
C1···O2	3.191 (3)	H10A···H8B^v	2.3391
C1···O4^i	3.245 (4)	H10B···H8C^iii	2.4114
C3···O4	3.154 (3)	H10C···H5^vi	2.5184
C9···O3^iii	3.319 (5)	H10C···Cl2^ix	3.0816
C2···H5	2.9838
C3—O1—C7	119.4 (2)	C3—C2—H2	118.33
C4—O2—C9	117.15 (18)	O1—C3—H3	110.24
C2—C1—C6	123.6 (3)	C2—C3—H3	110.17
C1—C2—C3	123.4 (2)	C4—C3—H3	110.22
O1—C3—C2	107.04 (19)	O2—C4—H4	110.28
O1—C3—C4	106.58 (19)	C3—C4—H4	110.31
C2—C3—C4	112.5 (2)	C5—C4—H4	110.31
O2—C4—C3	109.04 (19)	Cl1—C5—H5	108.03
O2—C4—C5	106.71 (19)	C4—C5—H5	108.04
C3—C4—C5	110.1 (2)	C6—C5—H5	108.06
Cl1—C5—C4	111.37 (17)	Cl2—C6—H6	109.12
Cl1—C5—C6	110.01 (17)	C1—C6—H6	109.08
C4—C5—C6	111.2 (2)	C5—C6—H6	109.11
Cl2—C6—C1	108.21 (18)	C7—C8—H8A	109.46
Cl2—C6—C5	109.35 (16)	C7—C8—H8B	109.48
C1—C6—C5	111.9 (2)	C7—C8—H8C	109.46
O1—C7—O3	122.5 (2)	H8A—C8—H8B	109.44
O1—C7—C8	111.5 (2)	H8A—C8—H8C	109.50
O3—C7—C8	126.0 (3)	H8B—C8—H8C	109.48
O2—C9—O4	122.4 (2)	C9—C10—H10A	109.48
O2—C9—C10	111.3 (3)	C9—C10—H10B	109.50
O4—C9—C10	126.4 (3)	C9—C10—H10C	109.51
C2—C1—H1	118.27	H10A—C10—H10B	109.45
C6—C1—H1	118.18	H10A—C10—H10C	109.44
C1—C2—H2	118.27	H10B—C10—H10C	109.46
C3—O1—C7—C8	−174.8 (2)	C2—C3—C4—C5	44.0 (3)
C3—O1—C7—O3	6.6 (4)	O1—C3—C4—C5	−73.0 (2)
C7—O1—C3—C2	120.1 (3)	C2—C3—C4—O2	−72.8 (2)
C7—O1—C3—C4	−119.3 (2)	O1—C3—C4—O2	170.22 (19)
C4—O2—C9—O4	3.6 (5)	O2—C4—C5—C6	57.9 (2)
C4—O2—C9—C10	−175.6 (2)	O2—C4—C5—Cl1	−65.2 (2)
C9—O2—C4—C5	157.4 (2)	C3—C4—C5—C6	−60.3 (2)
C9—O2—C4—C3	−83.7 (3)	C3—C4—C5—Cl1	176.58 (16)
C2—C1—C6—C5	−16.5 (3)	Cl1—C5—C6—C1	169.60 (16)
C6—C1—C2—C3	1.2 (4)	C4—C5—C6—Cl2	165.64 (16)
C2—C1—C6—Cl2	−137.1 (2)	Cl1—C5—C6—Cl2	−70.50 (18)
C1—C2—C3—C4	−15.3 (3)	C4—C5—C6—C1	45.7 (3)
C1—C2—C3—O1	101.4 (3)

Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+3/2, z−1/2; (iii) −x+1, −y+1, −z+1; (iv) x−1, y, z; (v) x+1, y, z+1; (vi) x, y, z+1; (vii) x, y, z−1; (viii) x−1, y, z−1; (ix) x−1/2, −y+3/2, z+1/2.