research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 72| Part 5| May 2016| Pages 709-711
doi:10.1107/S2056989016006174

Crystal structure of (1S,3R,8R,10S)-2,2-di­chloro-10-hy­dr­oxy-3,7,7,10-tetra­methyl­tri­cyclo­[6.4.0.01,3]dodecan-9-one

CROSSMARK_Color_square_no_text.svg
Ahmed Benzalim,a Aziz Auhmani,a* My Youssef Ait Itto,a Jean-Claude Daranb and Auhmani Abdelwaheda

aLaboratoire de Physico-Chimie Moléculaire et Synthèse Organique, Département de Chimie, Faculté des Sciences, Semlalia BP 2390, Marrakech 40001, Morocco, and bLaboratoire de Chimie de Coordination, CNRS UPR8241, 205 route de Narbonne, 31077 Toulouse Cedex 04, France
*Correspondence e-mail: a.auhmani@uca.ac.ma

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 5 April 2016; accepted 12 April 2016; online 15 April 2016)

The asymmetric unit of the title compound, C16H24Cl2O2, contains two independent mol­ecules (A and B) which are built from three fused rings, viz. a seven-membered heptane ring, a six-membered cyclo­hexyl ring bearing a ketone and an alcohol group, and a cyclo­propane ring bearing two Cl atoms. In the crystal, the two mol­ecules are linked via two O—H⋯O hydrogen bonds, forming an A–B dimer with an R22(10) ring motif. The A mol­ecules of these dimers are linked via a C—H⋯O hydrogen bond, forming chains propagating along the a-axis direction. Both mol­ecules have the same absolute configuration, i.e. 1S,3R,8R,10S, which is based on the synthetic pathway and further confirmed by resonant scattering [Flack parameter = 0.03 (5)].

CCDC reference: 1473671

1. Chemical context

α-Hy­droxy carbonyl groups are present in many compounds (such as α-ketols) with important biological activity (Murahashi et al., 1993[Murahashi, S.-I., Naota, T. & Hanaoka, H. (1993). Chem. Lett. pp. 1767-1770.]). The hy­droxy­ketone side chain is not just found in a large variety of anti-inflammatory corticosteroid drugs (Van Rheenen & Shephard, 1979[VanRheenen, V. & Shephard, K. P. (1979). J. Org. Chem. 44, 1582-1584.]), but is also a structural component of adriamycin, a potent anti­tumor agent (Tamura et al., 1985[Tamura, Y., Yakura, T., Haruta, J.-I. & Kita, Y. (1985). Tetrahedron Lett. 26, 3837-3840.]). As a result of their expanded occurrence and their biological activity, the development of methods for the direct asymmetric synthesis of α-hy­droxy ketones has grown significantly (Salvador et al., 2006[Salvador, J. A. R., Moreira, V. M., Hanson, J. R. & Carvalho, R. A. (2006). Steroids, 71, 266-272.]). In a tentative attempt to prepare new α-hy­droxy ketones with a natural product skeleton, we synthesized the title compound by oxidative ring-opening of (1S,3R,8S,9R,10S)-2,2-di­chloro-3,7,7,10-tetra­methyl-9,10-ep­oxy­tri­cyclo­[6.4.0.01,3]dodecane (Sbai et al., 2002[Sbai, F., Dakir, M., Auhmani, A., El Jamili, H., Akssira, M., Benharref, A., Kenz, A. & Pierrot, M. (2002). Acta Cryst. C58, o518-o520.]), using aqueous CrO3 (Trost & Fray, 1988[Trost, B. M. & Fray, M. J. (1988). Tetrahedron Lett. 29, 2163-2166.]).

[Scheme 1]

2. Structural commentary

There are two mol­ecules (A and B) in the asymmetric unit of the title compound, Fig. 1[link], both having the same the absolute configuration: (1S,3R,8R,10S) and (1AS,3AR,8AR,10AS). The compound is built up from three fused rings: a seven-membered heptane ring, a six-membered cyclo­hexyl ring bearing a ketone and alcohol groups, and a three-membered propane ring bearing two Cl atoms (Fig. 1[link]). In mol­ecule B (Fig. 2[link]), there is positional disorder affecting the location of atom C6 which is split over two positions, C6a and C6b. In both mol­ecules, the six-membered rings display a conformation inter­mediate between boat and twist-boat with puckering parameters θ = 89.73 and φ2 = 198.07° for mol­ecule A and θ = 91.78 and φ2 = 210.97° for mol­ecule B. The seven-membered cyclo­heptane ring in mol­ecule A displays a conformation inter­mediate between boat and twist-boat with puckering parameters q2 = 1.151 (5) and q3 = 0.030 (5) Å. Owing to the disorder observed in mol­ecule B within the seven-membered ring, the conformation of this ring is inter­mediate between boat and twist-boat [q2 = 1.194 (5), q3 = 0.00 (4) Å] or chair and twist-chair [q2 = 0.363 (5), q3 = 0.784 (5) Å], depending on the position of atom C6a or C6b.

[Figure 1]
Figure 1
A view of the mol­ecular structure of the two independent mol­ecules of the title compound, showing the atom labelling. Displacement ellipsoid are drawn at the 50% probability level.
[Figure 2]
Figure 2
A view showing the disorder (dashed double lines) in mol­ecule B.

3. Supra­molecular features

The two independent mol­ecules are connected through O—H⋯O hydrogen bonds, involving the hydroxyl and the ketone O atoms, forming an A-B dimer with an R22(10) ring motif (Fig. 3[link] and Table 1[link]). The A mol­ecules of these dimers are linked via a C—H⋯O hydrogen bond forming chains propagating along the a axis direction (Fig. 3[link] and Table 1[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O10—H10⋯O9A 0.84 2.43 3.203 (7) 153
O10A—H10A⋯O9 0.84 2.11 2.945 (6) 173
C12—H12B⋯O10i 0.99 2.48 3.361 (7) 148
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].
[Figure 3]
Figure 3
Partial crystal packing of the title compound (mol­ecule A blue, mol­ecule B red), viewed along the c axis, showing the formation of the hydrogen-bonded chain parallel to the a-axis direction. The hydrogen bonds are shown as dashed lines (see Table 1[link]; H atom as balls) and H atoms not involved in these inter­actions have been omitted for clarity.

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.38, update February 2016; Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]) using a fused cyclo­hexyl, cyclo­heptane and cyclo­propane bearing two Cl atoms, the same main skeleton as in the title compound, revealed the presence of eight structures with similar cyclo­heptane rings. One of these concerns the starting reagent (XOSFUG; Sbai et al., 2002[Sbai, F., Dakir, M., Auhmani, A., El Jamili, H., Akssira, M., Benharref, A., Kenz, A. & Pierrot, M. (2002). Acta Cryst. C58, o518-o520.]) for the synthesis of the title compound – see Section 5. Synthesis and crystallization. In another compound, the cyclo­heptane ring is fused with a cyclo­hexane ring bearing a ketone group, viz. (1S,3R,8S,10R)-2,2-di­chloro-3,7,7,10-tetra­methyl­tri­cyclo­(6.4.0.01,3)dodec-9-one (XOSGAN; Sbai et al., 2002[Sbai, F., Dakir, M., Auhmani, A., El Jamili, H., Akssira, M., Benharref, A., Kenz, A. & Pierrot, M. (2002). Acta Cryst. C58, o518-o520.]). A search for a cyclo­hexa­n­one ring revealed the occurrence of one structure having a similar hy­droxy cyclo­hexa­none ring, viz. 6-(2-(3,4-dihy­droxy-4-methyl­cyclo­hex­yl)prop-2-en-1-yl)-2-hy­droxy-2-methyl-5-(prop-1-en-2-yl)cyclo­hexa­none monohydrate (BUXNAK; Blair et al., 2010[Blair, M., Forsyth, C. M. & Tuck, K. L. (2010). Tetrahedron Lett. 51, 4808-4811.]).

5. Synthesis and crystallization

To a solution of 0.4 g (1.319 mmol) of (1S,3R,8S,9R,10S)-2,2-di­chloro-3,7,7,10-tetra­methyl-9,10-ep­oxy­tri­cyclo­[6.4.0.01,3]dodecane (Sbai et al., 2002[Sbai, F., Dakir, M., Auhmani, A., El Jamili, H., Akssira, M., Benharref, A., Kenz, A. & Pierrot, M. (2002). Acta Cryst. C58, o518-o520.]) in acetone (8 ml), 3 ml of an aqueous solution of CrO3 (1 g, 10 mmol) was added at 273 K. The mixture was stirred at room temperature for 30 min and cooled to 273 K in an ice bath and 1.5 ml of an aqueous solution of CrO3 (0,5 g, 5 mmol) was added dropwise. The ice bath was removed and the mixture was stirred at room temperature for 1 h. The reaction mixture was extracted with di­chloro­methane (3 × 30 ml) and the organic layers were dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was then purified on silica gel chromatography (230–400 mesh) using hexa­ne/ethyl acetate (95:5) as eluent to give the title compound (yield 53%). Colourless plate-like crystals were obtained from a petroleum ether solution, by slow evaporation of the solvent at room temperature.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The OH and C-bound H atoms were included in calculated positions and refined as riding: O—H = 0.84, C—H = 0.98–1.00 Å with Uiso(H) = 1.5Ueq(O and C-meth­yl) and 1.2Ueq(C) for other H atoms. The disordered cyclo­heptane ring in mol­ecule B was refined by splitting atoms C6a, C14a and C15a over two positions. The occupancy factors were initially refined and once the occupancy was correctly evaluated the values were held fixed with ratio 0.54:0.46. Atoms C5a and C7a were also split (C5a/C5b and C7a/C7b) and constrained to occupy the same site using EXYZ and EADP commands allowing then to locate the H atoms.

Table 2
Experimental details

Crystal data
Chemical formula C16H24Cl2O2
Mr 319.25
Crystal system, space group Orthorhombic, P212121
Temperature (K) 173
a, b, c (Å) 9.6745 (3), 13.9432 (6), 23.3654 (10)
V (Å3) 3151.8 (2)
Z 8
Radiation type Mo Kα
μ (mm−1) 0.41
Crystal size (mm) 0.45 × 0.35 × 0.10
 
Data collection
Diffractometer Agilent Xcalibur (Eos, Gemini ultra)
Absorption correction Multi-scan (CrysAlis PRO; Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd., Yarnton, England.])
Tmin, Tmax 0.974, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 16637, 5991, 5182
Rint 0.062
(sin θ/λ)max (Å−1) 0.617
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.134, 1.07
No. of reflections 5991
No. of parameters 376
No. of restraints 12
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.73, −0.46
Absolute structure Flack x determined using 1835 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])
Absolute structure parameter 0.03 (5)
Computer programs: CrysAlis PRO (Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd., Yarnton, England.]), SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

CCDC reference: 1473671

Crystal structure: contains datablocks I, Global. DOI: 10.1107/S2056989016006174/su5293sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989016006174/su5293Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989016006174/su5293Isup3.cml

checkCIF report


Chemical context top

\ α-Hy­droxy carbonyl groups are present in many compounds (such as α-ketols) with important biological activity (Murahashi et al., 1993). The hy­droxy­ketone side chain is not just found in a large variety of anti-inflammatory corticosteroid drugs (Van Rheenen & Shephard, 1979), but is also a structural component of adriamycin, a potent anti­tumor agent (Tamura et al., 1985). As a result of their expanded occurrence and their biological activity, the development of methods for the direct asymmetric synthesis of α-hy­droxy ketones has grown significantly (Salvador et al., 2006). In a tentative attempt to prepare new α-hy­droxy ketones with a natural product skeleton, we synthesized the title compound by oxidative ring-opening of (1S,3R,8S,9R,10S)-2,2-di­chloro-3,7,7,10-\ tetra­methyl-9,10-ep­oxy­tri­cyclo­[6.4.0.01,3]do­decane (Sbai et al., 2002), using aqueous CrO3 (Trost & Fray, 1988).

Structural commentary top

There are two molecules (A and B) in the asymmetric unit of the title compound, Fig. 1, both having the same the absolute configuration: (1S,3R,8R,10S) and (1AS,3AR,8AR,10AS). The compound is built up from three fused rings: a seven-membered heptane ring, a six-membered cyclo­hexyl ring bearing a ketone and alcohol groups, and a three-membered propane ring bearing two Cl atoms (Fig. 1). In molecule B (Fig. 2), there is positional disorder affecting the location of atom C6 which is split over two positions, C6a and C6b. In both molecules, the six-membered rings display a conformation inter­mediate between boat and twist-boat with puckering parameters θ = 89.73 and φ2 = 198.07° for molecule A and θ = 91.78 and φ2 = 210.97° for molecule B. The seven-membered cyclo­heptane ring in molecule A displays a conformation inter­mediate between boat and twist-boat with puckering parameters q2 = 1.151 (5) and q3 = 0.030 (5) Å. Owing to the disorder observed in molecule B within the seven-membered ring, the conformation of this ring is inter­mediate between boat and twist-boat [q2 = 1.194 (5), q3 = 0.00 (4) Å] or chair and twist-chair [q2 = 0.363 (5), q3 = 0.784 (5) Å], depending on the position of atom C6a or C6b.

Supra­molecular features top

The two independent molecules are connected through O—H···O hydrogen bonds, involving the hydroxyl and the ketone O atoms, forming an A—B dimer with an R22(10) ring motif (Fig. 3 and Table 1). The A molecules of these dimers are linked via a C—H···O hydrogen bond forming chains propagating along the a axis direction (Fig. 3 and Table 1).

Database survey top

\ A search of the Cambridge Structural Database (CSD, Version 5.38, update February 2016; Groom et al., 2016) using a fused cyclo­hexyl, cyclo­heptane and cyclo­propane bearing two Cl atoms, the same main skeleton as in the title compound, revealed the presence of eight structures with similar cyclo­heptane rings. One of these concerns the starting reagent (XOSFUG; Sbai et al., 2002) for the synthesis of the title compound – see Section 5. Synthesis and crystallization. In another compound, the cyclo­heptane ring is fused with a cyclo­hexane ring bearing a ketone group, viz. (1S,3R,8S,10R)-2,2-di­chloro-3,7,7,10-\ tetra­methyl­tri­cyclo­(6.4.0.01,3) dodec-9-one (XOSGAN; Sbai et al., 2002). A search for a cyclo­hexanone ring revealed the occurrence of one structure having a similar hy­droxy cyclo­hexanone ring, viz. 6-(2-(3,4-di­hydroxy-4-methyl­cyclo­hexyl)­prop-2-en-1-yl)-2-hy­droxy-2-methyl- 5-(prop-1-en-2-yl)cyclo­hexanone monohydrate (BUXNAK; Blair et al., 2010).

Synthesis and crystallization top

\ To a solution of 0.4 g (1.319 mmol) of (1S,3R,8S,9R,10S)-2,2-di­chloro-3,7,7,10-\ tetra­methyl-9,10-ep­oxy­tri­cyclo­[6.4.0.01,3]do­decane (Sbai et al., 2002) in acetone (8 ml), 3 ml of an aqueous solution of CrO3 (1 g, 10 mmol) was added at 273 K. The mixture was stirred at room temperature for 30 min and cooled to 273 K in an ice bath and 1.5 ml of an aqueous solution of CrO3 (0,5 g, 5 mmol) was added dropwise. The ice bath was removed and the mixture was stirred at room temperature for 1 h. The reaction mixture was extracted with di­chloro­methane (3 × 30 ml) and the organic layers were dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was then purified on silica gel chromatography (230–400 mesh) using hexane/ethyl acetate (95:5) as eluent to give the title compound (yield 53%). Colourless plate-like crystals were obtained from a petroleum ether solution, by slow evaporation of the solvent at ambient temperature.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The OH and C-bound H atoms were included in calculated positions and refined as riding: O—H = 0.84, C—H = 0.98–1.00 Å with Uiso(H) = 1.5Ueq(O and C-methyl) and 1.2Ueq(C) for other H atoms. The disordered cyclo­heptane ring in molecule B was refined by splitting atoms C6a, C14a and C15a over two positions. The occupancy factors were initially refined and once the occupancy was correctly evaluated the values were held fixed with ratio 0.54:0.46. Atoms C5a and C7a were also split (C5a/C5b and C7a/C7b) and constrained to occupy the same site using EXYZ and EADP commands allowing then to locate the H atoms.

Structure description top

\ α-Hy­droxy carbonyl groups are present in many compounds (such as α-ketols) with important biological activity (Murahashi et al., 1993). The hy­droxy­ketone side chain is not just found in a large variety of anti-inflammatory corticosteroid drugs (Van Rheenen & Shephard, 1979), but is also a structural component of adriamycin, a potent anti­tumor agent (Tamura et al., 1985). As a result of their expanded occurrence and their biological activity, the development of methods for the direct asymmetric synthesis of α-hy­droxy ketones has grown significantly (Salvador et al., 2006). In a tentative attempt to prepare new α-hy­droxy ketones with a natural product skeleton, we synthesized the title compound by oxidative ring-opening of (1S,3R,8S,9R,10S)-2,2-di­chloro-3,7,7,10-\ tetra­methyl-9,10-ep­oxy­tri­cyclo­[6.4.0.01,3]do­decane (Sbai et al., 2002), using aqueous CrO3 (Trost & Fray, 1988).

There are two molecules (A and B) in the asymmetric unit of the title compound, Fig. 1, both having the same the absolute configuration: (1S,3R,8R,10S) and (1AS,3AR,8AR,10AS). The compound is built up from three fused rings: a seven-membered heptane ring, a six-membered cyclo­hexyl ring bearing a ketone and alcohol groups, and a three-membered propane ring bearing two Cl atoms (Fig. 1). In molecule B (Fig. 2), there is positional disorder affecting the location of atom C6 which is split over two positions, C6a and C6b. In both molecules, the six-membered rings display a conformation inter­mediate between boat and twist-boat with puckering parameters θ = 89.73 and φ2 = 198.07° for molecule A and θ = 91.78 and φ2 = 210.97° for molecule B. The seven-membered cyclo­heptane ring in molecule A displays a conformation inter­mediate between boat and twist-boat with puckering parameters q2 = 1.151 (5) and q3 = 0.030 (5) Å. Owing to the disorder observed in molecule B within the seven-membered ring, the conformation of this ring is inter­mediate between boat and twist-boat [q2 = 1.194 (5), q3 = 0.00 (4) Å] or chair and twist-chair [q2 = 0.363 (5), q3 = 0.784 (5) Å], depending on the position of atom C6a or C6b.

The two independent molecules are connected through O—H···O hydrogen bonds, involving the hydroxyl and the ketone O atoms, forming an A—B dimer with an R22(10) ring motif (Fig. 3 and Table 1). The A molecules of these dimers are linked via a C—H···O hydrogen bond forming chains propagating along the a axis direction (Fig. 3 and Table 1).

\ A search of the Cambridge Structural Database (CSD, Version 5.38, update February 2016; Groom et al., 2016) using a fused cyclo­hexyl, cyclo­heptane and cyclo­propane bearing two Cl atoms, the same main skeleton as in the title compound, revealed the presence of eight structures with similar cyclo­heptane rings. One of these concerns the starting reagent (XOSFUG; Sbai et al., 2002) for the synthesis of the title compound – see Section 5. Synthesis and crystallization. In another compound, the cyclo­heptane ring is fused with a cyclo­hexane ring bearing a ketone group, viz. (1S,3R,8S,10R)-2,2-di­chloro-3,7,7,10-\ tetra­methyl­tri­cyclo­(6.4.0.01,3) dodec-9-one (XOSGAN; Sbai et al., 2002). A search for a cyclo­hexanone ring revealed the occurrence of one structure having a similar hy­droxy cyclo­hexanone ring, viz. 6-(2-(3,4-di­hydroxy-4-methyl­cyclo­hexyl)­prop-2-en-1-yl)-2-hy­droxy-2-methyl- 5-(prop-1-en-2-yl)cyclo­hexanone monohydrate (BUXNAK; Blair et al., 2010).

Synthesis and crystallization top

\ To a solution of 0.4 g (1.319 mmol) of (1S,3R,8S,9R,10S)-2,2-di­chloro-3,7,7,10-\ tetra­methyl-9,10-ep­oxy­tri­cyclo­[6.4.0.01,3]do­decane (Sbai et al., 2002) in acetone (8 ml), 3 ml of an aqueous solution of CrO3 (1 g, 10 mmol) was added at 273 K. The mixture was stirred at room temperature for 30 min and cooled to 273 K in an ice bath and 1.5 ml of an aqueous solution of CrO3 (0,5 g, 5 mmol) was added dropwise. The ice bath was removed and the mixture was stirred at room temperature for 1 h. The reaction mixture was extracted with di­chloro­methane (3 × 30 ml) and the organic layers were dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was then purified on silica gel chromatography (230–400 mesh) using hexane/ethyl acetate (95:5) as eluent to give the title compound (yield 53%). Colourless plate-like crystals were obtained from a petroleum ether solution, by slow evaporation of the solvent at ambient temperature.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 2. The OH and C-bound H atoms were included in calculated positions and refined as riding: O—H = 0.84, C—H = 0.98–1.00 Å with Uiso(H) = 1.5Ueq(O and C-methyl) and 1.2Ueq(C) for other H atoms. The disordered cyclo­heptane ring in molecule B was refined by splitting atoms C6a, C14a and C15a over two positions. The occupancy factors were initially refined and once the occupancy was correctly evaluated the values were held fixed with ratio 0.54:0.46. Atoms C5a and C7a were also split (C5a/C5b and C7a/C7b) and constrained to occupy the same site using EXYZ and EADP commands allowing then to locate the H atoms.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the two independent molecules of the title compound, showing the atom labelling. Displacement ellipsoid are drawn at the 50% probability level.
[Figure 2] Fig. 2. A view showing the disorder (dashed double lines) in molecule B.
[Figure 3] Fig. 3. Partial crystal packing of the title compound (molecule A blue, molecule B red), viewed along the c axis, showing the formation of the hydrogen-bonded chain parallel to the a-axis direction. The hydrogen bonds are shown as dashed lines (see Table 1; H atom as balls) and H atoms not involved in these interactions have been omitted for clarity.
(1S,3R,8R,10S)-2,2-Dichloro-10-hydroxy-3,7,7,10-tetramethyltricyclo[6.4.0.01,3]dodecan-9-one top
Crystal data top
C16H24Cl2O2Dx = 1.346 Mg m−3
Mr = 319.25Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 6322 reflections
a = 9.6745 (3) Åθ = 3.7–27.0°
b = 13.9432 (6) ŵ = 0.41 mm−1
c = 23.3654 (10) ÅT = 173 K
V = 3151.8 (2) Å3Plate, colourless
Z = 80.45 × 0.35 × 0.10 mm
F(000) = 1360
Data collection top
Agilent Xcalibur (Eos, Gemini ultra)
diffractometer		5991 independent reflections
Radiation source: Enhance (Mo) X-ray Source5182 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
Detector resolution: 16.1978 pixels mm-1θmax = 26.0°, θmin = 3.1°
ω scansh = −11→11
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)		k = −15→17
Tmin = 0.974, Tmax = 1.000l = −28→27
16637 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.052 w = 1/[σ2(Fo2) + (0.0594P)2 + 0.805P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.134(Δ/σ)max < 0.001
S = 1.07Δρmax = 0.73 e Å−3
5991 reflectionsΔρmin = −0.46 e Å−3
376 parametersAbsolute structure: Flack x determined using 1835 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
12 restraintsAbsolute structure parameter: 0.03 (5)
Crystal data top
C16H24Cl2O2V = 3151.8 (2) Å3
Mr = 319.25Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 9.6745 (3) ŵ = 0.41 mm−1
b = 13.9432 (6) ÅT = 173 K
c = 23.3654 (10) Å0.45 × 0.35 × 0.10 mm
Data collection top
Agilent Xcalibur (Eos, Gemini ultra)
diffractometer		5991 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)		5182 reflections with I > 2σ(I)
Tmin = 0.974, Tmax = 1.000Rint = 0.062
16637 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.134Δρmax = 0.73 e Å−3
S = 1.07Δρmin = −0.46 e Å−3
5991 reflectionsAbsolute structure: Flack x determined using 1835 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
376 parametersAbsolute structure parameter: 0.03 (5)
12 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.0491 (5)0.0997 (4)0.40650 (19)0.0207 (10)
C20.0427 (5)−0.0041 (4)0.3866 (2)0.0229 (11)
C3−0.0896 (5)0.0502 (4)0.3921 (2)0.0240 (10)
C4−0.1630 (5)0.0827 (4)0.3381 (2)0.0273 (12)
H4A−0.23650.03600.32860.033*
H4B−0.09620.08360.30610.033*
C5−0.2276 (5)0.1830 (4)0.3446 (2)0.0305 (12)
H5A−0.24020.21140.30620.037*
H5B−0.32020.17640.36230.037*
C6−0.1411 (5)0.2509 (4)0.3809 (2)0.0284 (12)
H6A−0.13970.22510.42040.034*
H6B−0.19030.31310.38240.034*
C70.0096 (5)0.2716 (3)0.3636 (2)0.0226 (11)
C80.0986 (5)0.1750 (3)0.36409 (19)0.0192 (10)
H80.08930.14600.32510.023*
C90.2505 (5)0.1979 (4)0.3721 (2)0.0249 (11)
C100.3245 (5)0.1663 (4)0.4267 (2)0.0315 (12)
C110.2258 (6)0.1708 (4)0.4777 (2)0.0313 (13)
H11A0.20870.23900.48710.038*
H11B0.27190.14120.51110.038*
C120.0859 (5)0.1211 (4)0.46868 (19)0.0255 (11)
H12A0.08610.06000.49020.031*
H12B0.01260.16220.48520.031*
C13−0.1889 (5)0.0269 (4)0.4410 (2)0.0353 (13)
H13A−0.2373−0.03320.43270.053*
H13B−0.25640.07890.44510.053*
H13C−0.13670.02010.47670.053*
C140.0144 (6)0.3136 (4)0.3030 (2)0.0328 (13)
H14A−0.04310.37140.30140.049*
H14B−0.02060.26620.27570.049*
H14C0.11000.33020.29330.049*
C150.0628 (6)0.3474 (4)0.4049 (2)0.0310 (12)
H15A0.01630.40850.39730.046*
H15B0.16270.35530.39980.046*
H15C0.04380.32730.44430.046*
C160.3835 (6)0.0654 (4)0.4177 (3)0.0396 (14)
H16A0.44860.06620.38560.059*
H16B0.30800.02070.40930.059*
H16C0.43160.04470.45250.059*
O90.3149 (4)0.2414 (3)0.33530 (17)0.0364 (9)
O100.4396 (4)0.2273 (3)0.4373 (2)0.0477 (11)
H100.43800.27360.41430.072*
Cl10.10699 (13)−0.03802 (9)0.31897 (5)0.0289 (3)
Cl20.07611 (14)−0.09878 (9)0.43518 (6)0.0331 (3)
C1A0.6252 (5)0.6364 (4)0.3446 (2)0.0236 (11)
C2A0.7685 (5)0.6191 (4)0.3695 (2)0.0249 (11)
C3A0.7087 (5)0.7175 (4)0.3728 (2)0.0235 (11)
C4A0.6605 (6)0.7556 (4)0.4303 (2)0.0332 (12)
H4A10.65040.70100.45710.040*
H4A20.73270.79860.44590.040*
C5A0.5252 (6)0.8098 (4)0.4280 (3)0.0408 (14)0.54
H5A10.54570.87910.42410.049*0.54
H5A20.47640.80070.46490.049*0.54
C6A0.4225 (9)0.7787 (6)0.3768 (4)0.0322 (18)0.54
H6A10.34030.82100.37710.039*0.54
H6A20.47020.78740.33970.039*0.54
C7A0.3742 (5)0.6705 (4)0.3827 (2)0.0373 (14)0.54
C14A0.2879 (11)0.6532 (10)0.4336 (4)0.0436 (17)0.54
H14D0.21930.70460.43720.065*0.54
H14E0.34640.65210.46780.065*0.54
H14F0.24040.59140.42970.065*0.54
C15A0.2798 (10)0.6644 (10)0.3284 (4)0.0436 (17)0.54
H15D0.24650.59850.32370.065*0.54
H15E0.33290.68320.29450.065*0.54
H15F0.20070.70760.33300.065*0.54
C8A0.5004 (5)0.5996 (4)0.3788 (2)0.0241 (11)
H8A0.53410.59130.41890.029*
C5B0.5252 (6)0.8098 (4)0.4280 (3)0.0408 (14)0.46
H5B10.51350.84030.39000.049*0.46
H5B20.52370.86060.45760.049*0.46
C6B0.4056 (10)0.7356 (7)0.4391 (4)0.0322 (18)0.46
H6B10.32060.77060.45010.039*0.46
H6B20.43160.69330.47130.039*0.46
C7B0.3742 (5)0.6705 (4)0.3827 (2)0.0373 (14)0.46
C14B0.2512 (11)0.6156 (11)0.4076 (6)0.0436 (17)0.46
H14G0.18480.66120.42380.065*0.46
H14H0.28360.57220.43770.065*0.46
H14I0.20650.57840.37730.065*0.46
C15B0.3436 (13)0.7365 (10)0.3366 (5)0.0436 (17)0.46
H15G0.30900.70060.30350.065*0.46
H15H0.42780.77110.32590.065*0.46
H15I0.27310.78240.34920.065*0.46
C9A0.4633 (5)0.4997 (4)0.3580 (2)0.0308 (13)
C10A0.4967 (6)0.4694 (4)0.2964 (2)0.0347 (13)
C11A0.5131 (8)0.5565 (5)0.2563 (3)0.0525 (17)
H11C0.54990.53420.21900.063*
H11D0.42090.58500.24920.063*
C12A0.6092 (6)0.6342 (4)0.2801 (2)0.0316 (12)
H12C0.70190.62530.26290.038*
H12D0.57430.69740.26750.038*
C13A0.7716 (6)0.7959 (4)0.3355 (2)0.0378 (14)
H13D0.85840.81790.35270.057*
H13E0.70700.84980.33280.057*
H13F0.78980.77040.29720.057*
C16A0.6231 (7)0.4100 (5)0.2982 (3)0.0505 (17)
H16D0.60340.34970.31820.076*
H16E0.69620.44470.31860.076*
H16F0.65360.39610.25910.076*
O9A0.4112 (5)0.4425 (3)0.3907 (2)0.0612 (14)
O10A0.3816 (5)0.4186 (4)0.2726 (2)0.0631 (14)
H10A0.36300.37110.29330.095*
Cl1A0.91022 (13)0.59664 (11)0.32401 (6)0.0384 (3)
Cl2A0.78988 (13)0.54934 (10)0.43211 (6)0.0347 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.024 (2)0.022 (2)0.016 (2)0.003 (2)−0.0005 (18)−0.005 (2)
C20.028 (2)0.019 (2)0.021 (2)−0.001 (2)0.003 (2)0.001 (2)
C30.025 (2)0.019 (2)0.028 (2)0.000 (2)0.002 (2)0.003 (2)
C40.024 (2)0.025 (3)0.033 (3)−0.003 (2)−0.007 (2)−0.005 (2)
C50.026 (2)0.029 (3)0.037 (3)0.005 (2)−0.004 (2)0.005 (3)
C60.034 (3)0.026 (3)0.025 (3)0.005 (2)0.002 (2)0.000 (2)
C70.030 (2)0.013 (2)0.025 (3)0.000 (2)0.004 (2)0.001 (2)
C80.025 (2)0.016 (2)0.017 (2)0.003 (2)0.0004 (19)−0.004 (2)
C90.027 (3)0.021 (3)0.026 (3)0.002 (2)0.003 (2)−0.010 (2)
C100.024 (2)0.037 (3)0.034 (3)−0.003 (2)−0.009 (2)−0.008 (3)
C110.041 (3)0.029 (3)0.023 (3)0.004 (3)−0.012 (2)−0.005 (2)
C120.033 (3)0.029 (3)0.015 (2)0.007 (3)0.000 (2)−0.002 (2)
C130.030 (3)0.032 (3)0.044 (3)0.001 (2)0.010 (2)0.004 (3)
C140.042 (3)0.029 (3)0.028 (3)0.008 (3)0.005 (2)0.005 (3)
C150.033 (3)0.025 (3)0.035 (3)0.006 (2)0.003 (2)−0.004 (2)
C160.032 (3)0.035 (3)0.051 (4)0.008 (3)−0.013 (3)−0.003 (3)
O90.0342 (19)0.030 (2)0.045 (2)−0.0094 (18)0.0140 (18)−0.0039 (19)
O100.038 (2)0.044 (2)0.062 (3)−0.011 (2)−0.016 (2)−0.008 (2)
Cl10.0373 (7)0.0254 (6)0.0241 (6)0.0032 (6)0.0005 (5)−0.0078 (6)
Cl20.0416 (7)0.0243 (6)0.0334 (7)0.0054 (6)−0.0017 (6)0.0071 (6)
C1A0.024 (2)0.024 (3)0.023 (3)−0.003 (2)0.002 (2)−0.002 (2)
C2A0.022 (2)0.027 (3)0.026 (3)0.001 (2)−0.001 (2)0.001 (2)
C3A0.025 (2)0.019 (2)0.026 (3)−0.001 (2)−0.004 (2)0.003 (2)
C4A0.048 (3)0.022 (3)0.029 (3)−0.003 (2)−0.003 (3)0.002 (2)
C5A0.044 (3)0.027 (3)0.052 (4)0.003 (3)0.005 (3)−0.012 (3)
C6A0.031 (4)0.033 (4)0.032 (4)0.010 (4)0.000 (3)0.005 (4)
C7A0.025 (3)0.036 (3)0.050 (4)0.005 (3)0.002 (3)−0.002 (3)
C14A0.030 (3)0.060 (5)0.040 (4)0.015 (3)0.008 (3)0.009 (4)
C15A0.030 (3)0.060 (5)0.040 (4)0.015 (3)0.008 (3)0.009 (4)
C8A0.022 (2)0.022 (3)0.028 (3)0.000 (2)0.000 (2)−0.001 (2)
C5B0.044 (3)0.027 (3)0.052 (4)0.003 (3)0.005 (3)−0.012 (3)
C6B0.031 (4)0.033 (4)0.032 (4)0.010 (4)0.000 (3)0.005 (4)
C7B0.025 (3)0.036 (3)0.050 (4)0.005 (3)0.002 (3)−0.002 (3)
C14B0.030 (3)0.060 (5)0.040 (4)0.015 (3)0.008 (3)0.009 (4)
C15B0.030 (3)0.060 (5)0.040 (4)0.015 (3)0.008 (3)0.009 (4)
C9A0.025 (3)0.028 (3)0.040 (3)−0.004 (2)0.005 (2)−0.005 (3)
C10A0.040 (3)0.033 (3)0.031 (3)−0.008 (3)−0.009 (2)−0.010 (3)
C11A0.063 (4)0.048 (4)0.046 (4)−0.009 (4)−0.021 (3)0.004 (3)
C12A0.035 (3)0.036 (3)0.024 (3)−0.008 (3)0.001 (2)−0.004 (2)
C13A0.040 (3)0.032 (3)0.041 (3)−0.012 (3)−0.002 (3)0.011 (3)
C16A0.065 (4)0.047 (4)0.040 (3)0.011 (4)0.000 (3)−0.013 (3)
O9A0.077 (3)0.043 (3)0.064 (3)−0.033 (3)0.043 (3)−0.012 (2)
O10A0.065 (3)0.065 (3)0.059 (3)−0.025 (3)−0.032 (3)0.002 (3)
Cl1A0.0246 (6)0.0456 (8)0.0450 (8)0.0026 (6)0.0110 (6)0.0044 (7)
Cl2A0.0345 (6)0.0351 (7)0.0345 (7)0.0095 (6)0.0003 (6)0.0135 (6)
Geometric parameters (Å, º) top
C1—C81.521 (7)C3A—C13A1.523 (7)
C1—C21.521 (7)C4A—C5B1.513 (8)
C1—C121.525 (6)C4A—C5A1.513 (8)
C1—C31.547 (7)C4A—H4A10.9900
C2—C31.493 (7)C4A—H4A20.9900
C2—Cl11.764 (5)C5A—C6A1.614 (8)
C2—Cl21.770 (5)C5A—H5A10.9900
C3—C41.515 (7)C5A—H5A20.9900
C3—C131.529 (7)C6A—C7A1.586 (8)
C4—C51.539 (7)C6A—H6A10.9900
C4—H4A0.9900C6A—H6A20.9900
C4—H4B0.9900C7A—C14A1.473 (9)
C5—C61.522 (7)C7A—C15A1.566 (9)
C5—H5A0.9900C7A—C8A1.574 (7)
C5—H5B0.9900C14A—H14D0.9800
C6—C71.540 (7)C14A—H14E0.9800
C6—H6A0.9900C14A—H14F0.9800
C6—H6B0.9900C15A—H15D0.9800
C7—C151.523 (7)C15A—H15E0.9800
C7—C141.532 (7)C15A—H15F0.9800
C7—C81.599 (6)C8A—C9A1.517 (7)
C8—C91.515 (7)C8A—C7B1.574 (7)
C8—H81.0000C8A—H8A1.0000
C9—O91.222 (6)C5B—C6B1.574 (9)
C9—C101.528 (7)C5B—H5B10.9900
C10—O101.422 (6)C5B—H5B20.9900
C10—C111.528 (8)C6B—C7B1.628 (9)
C10—C161.533 (8)C6B—H6B10.9900
C11—C121.536 (7)C6B—H6B20.9900
C11—H11A0.9900C7B—C15B1.448 (10)
C11—H11B0.9900C7B—C14B1.529 (10)
C12—H12A0.9900C14B—H14G0.9800
C12—H12B0.9900C14B—H14H0.9800
C13—H13A0.9800C14B—H14I0.9800
C13—H13B0.9800C15B—H15G0.9800
C13—H13C0.9800C15B—H15H0.9800
C14—H14A0.9800C15B—H15I0.9800
C14—H14B0.9800C9A—O9A1.214 (7)
C14—H14C0.9800C9A—C10A1.535 (8)
C15—H15A0.9800C10A—O10A1.432 (6)
C15—H15B0.9800C10A—C16A1.478 (8)
C15—H15C0.9800C10A—C11A1.543 (9)
C16—H16A0.9800C11A—C12A1.532 (8)
C16—H16B0.9800C11A—H11C0.9900
C16—H16C0.9800C11A—H11D0.9900
O10—H100.8400C12A—H12C0.9900
C1A—C12A1.515 (7)C12A—H12D0.9900
C1A—C2A1.522 (7)C13A—H13D0.9800
C1A—C8A1.535 (7)C13A—H13E0.9800
C1A—C3A1.537 (7)C13A—H13F0.9800
C2A—C3A1.491 (7)C16A—H16D0.9800
C2A—Cl1A1.763 (5)C16A—H16E0.9800
C2A—Cl2A1.769 (5)C16A—H16F0.9800
C3A—C4A1.520 (7)O10A—H10A0.8400
C8—C1—C2118.1 (4)C13A—C3A—C1A119.6 (4)
C8—C1—C12114.4 (4)C5B—C4A—C3A114.1 (5)
C2—C1—C12119.1 (4)C5A—C4A—C3A114.1 (5)
C8—C1—C3116.1 (4)C5A—C4A—H4A1108.7
C2—C1—C358.2 (3)C3A—C4A—H4A1108.7
C12—C1—C3119.8 (4)C5A—C4A—H4A2108.7
C3—C2—C161.8 (3)C3A—C4A—H4A2108.7
C3—C2—Cl1121.0 (4)H4A1—C4A—H4A2107.6
C1—C2—Cl1121.0 (3)C4A—C5A—C6A115.2 (5)
C3—C2—Cl2118.7 (3)C4A—C5A—H5A1108.5
C1—C2—Cl2120.5 (4)C6A—C5A—H5A1108.5
Cl1—C2—Cl2108.0 (3)C4A—C5A—H5A2108.5
C2—C3—C4118.9 (4)C6A—C5A—H5A2108.5
C2—C3—C13119.6 (4)H5A1—C5A—H5A2107.5
C4—C3—C13113.1 (4)C7A—C6A—C5A111.9 (6)
C2—C3—C160.0 (3)C7A—C6A—H6A1109.2
C4—C3—C1117.0 (4)C5A—C6A—H6A1109.2
C13—C3—C1118.5 (4)C7A—C6A—H6A2109.2
C3—C4—C5112.3 (4)C5A—C6A—H6A2109.2
C3—C4—H4A109.1H6A1—C6A—H6A2107.9
C5—C4—H4A109.1C14A—C7A—C15A108.3 (7)
C3—C4—H4B109.1C14A—C7A—C8A112.6 (6)
C5—C4—H4B109.1C15A—C7A—C8A111.8 (5)
H4A—C4—H4B107.9C14A—C7A—C6A113.1 (7)
C6—C5—C4113.4 (4)C15A—C7A—C6A98.8 (6)
C6—C5—H5A108.9C8A—C7A—C6A111.4 (5)
C4—C5—H5A108.9C7A—C14A—H14D109.5
C6—C5—H5B108.9C7A—C14A—H14E109.5
C4—C5—H5B108.9H14D—C14A—H14E109.5
H5A—C5—H5B107.7C7A—C14A—H14F109.5
C5—C6—C7119.4 (4)H14D—C14A—H14F109.5
C5—C6—H6A107.5H14E—C14A—H14F109.5
C7—C6—H6A107.5C7A—C15A—H15D109.5
C5—C6—H6B107.5C7A—C15A—H15E109.5
C7—C6—H6B107.5H15D—C15A—H15E109.5
H6A—C6—H6B107.0C7A—C15A—H15F109.5
C15—C7—C14108.1 (4)H15D—C15A—H15F109.5
C15—C7—C6106.5 (4)H15E—C15A—H15F109.5
C14—C7—C6110.1 (4)C9A—C8A—C1A109.1 (4)
C15—C7—C8113.4 (4)C9A—C8A—C7A114.3 (4)
C14—C7—C8108.2 (4)C1A—C8A—C7A115.5 (4)
C6—C7—C8110.5 (4)C9A—C8A—C7B114.3 (4)
C9—C8—C1111.8 (4)C1A—C8A—C7B115.5 (4)
C9—C8—C7110.3 (4)C9A—C8A—H8A105.7
C1—C8—C7114.6 (4)C1A—C8A—H8A105.7
C9—C8—H8106.6C7A—C8A—H8A105.7
C1—C8—H8106.6C4A—C5B—C6B107.6 (6)
C7—C8—H8106.6C4A—C5B—H5B1110.2
O9—C9—C8120.8 (5)C6B—C5B—H5B1110.2
O9—C9—C10119.4 (4)C4A—C5B—H5B2110.2
C8—C9—C10119.8 (4)C6B—C5B—H5B2110.2
O10—C10—C9109.9 (5)H5B1—C5B—H5B2108.5
O10—C10—C11109.2 (4)C5B—C6B—C7B111.8 (6)
C9—C10—C11110.3 (4)C5B—C6B—H6B1109.3
O10—C10—C16106.4 (4)C7B—C6B—H6B1109.3
C9—C10—C16108.9 (4)C5B—C6B—H6B2109.3
C11—C10—C16112.1 (5)C7B—C6B—H6B2109.3
C10—C11—C12115.2 (4)H6B1—C6B—H6B2107.9
C10—C11—H11A108.5C15B—C7B—C14B116.2 (8)
C12—C11—H11A108.5C15B—C7B—C8A121.0 (6)
C10—C11—H11B108.5C14B—C7B—C8A108.2 (6)
C12—C11—H11B108.5C15B—C7B—C6B106.6 (8)
H11A—C11—H11B107.5C14B—C7B—C6B96.7 (7)
C1—C12—C11115.1 (4)C8A—C7B—C6B104.7 (5)
C1—C12—H12A108.5C7B—C14B—H14G109.5
C11—C12—H12A108.5C7B—C14B—H14H109.5
C1—C12—H12B108.5H14G—C14B—H14H109.5
C11—C12—H12B108.5C7B—C14B—H14I109.5
H12A—C12—H12B107.5H14G—C14B—H14I109.5
C3—C13—H13A109.5H14H—C14B—H14I109.5
C3—C13—H13B109.5C7B—C15B—H15G109.5
H13A—C13—H13B109.5C7B—C15B—H15H109.5
C3—C13—H13C109.5H15G—C15B—H15H109.5
H13A—C13—H13C109.5C7B—C15B—H15I109.5
H13B—C13—H13C109.5H15G—C15B—H15I109.5
C7—C14—H14A109.5H15H—C15B—H15I109.5
C7—C14—H14B109.5O9A—C9A—C8A120.1 (5)
H14A—C14—H14B109.5O9A—C9A—C10A119.7 (5)
C7—C14—H14C109.5C8A—C9A—C10A120.2 (5)
H14A—C14—H14C109.5O10A—C10A—C16A112.2 (5)
H14B—C14—H14C109.5O10A—C10A—C9A109.7 (5)
C7—C15—H15A109.5C16A—C10A—C9A107.6 (5)
C7—C15—H15B109.5O10A—C10A—C11A103.4 (5)
H15A—C15—H15B109.5C16A—C10A—C11A111.9 (6)
C7—C15—H15C109.5C9A—C10A—C11A112.0 (5)
H15A—C15—H15C109.5C12A—C11A—C10A113.4 (5)
H15B—C15—H15C109.5C12A—C11A—H11C108.9
C10—C16—H16A109.5C10A—C11A—H11C108.9
C10—C16—H16B109.5C12A—C11A—H11D108.9
H16A—C16—H16B109.5C10A—C11A—H11D108.9
C10—C16—H16C109.5H11C—C11A—H11D107.7
H16A—C16—H16C109.5C1A—C12A—C11A116.0 (5)
H16B—C16—H16C109.5C1A—C12A—H12C108.3
C10—O10—H10109.5C11A—C12A—H12C108.3
C12A—C1A—C2A118.0 (4)C1A—C12A—H12D108.3
C12A—C1A—C8A115.4 (4)C11A—C12A—H12D108.3
C2A—C1A—C8A117.7 (4)H12C—C12A—H12D107.4
C12A—C1A—C3A119.6 (4)C3A—C13A—H13D109.5
C2A—C1A—C3A58.4 (3)C3A—C13A—H13E109.5
C8A—C1A—C3A115.9 (4)H13D—C13A—H13E109.5
C3A—C2A—C1A61.4 (3)C3A—C13A—H13F109.5
C3A—C2A—Cl1A119.7 (4)H13D—C13A—H13F109.5
C1A—C2A—Cl1A120.5 (4)H13E—C13A—H13F109.5
C3A—C2A—Cl2A120.6 (4)C10A—C16A—H16D109.5
C1A—C2A—Cl2A120.6 (4)C10A—C16A—H16E109.5
Cl1A—C2A—Cl2A108.0 (3)H16D—C16A—H16E109.5
C2A—C3A—C4A119.1 (4)C10A—C16A—H16F109.5
C2A—C3A—C13A118.4 (4)H16D—C16A—H16F109.5
C4A—C3A—C13A112.2 (4)H16E—C16A—H16F109.5
C2A—C3A—C1A60.3 (3)C10A—O10A—H10A109.5
C4A—C3A—C1A118.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O10—H10···O9A0.842.433.203 (7)153
O10A—H10A···O90.842.112.945 (6)173
C12—H12B···O10i0.992.483.361 (7)148
Symmetry code: (i) x−1/2, −y+1/2, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O10—H10···O9A0.842.433.203 (7)153
O10A—H10A···O90.842.112.945 (6)173
C12—H12B···O10i0.992.483.361 (7)148
Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formulaC16H24Cl2O2
Mr319.25
Crystal system, space groupOrthorhombic, P212121
Temperature (K)173
a, b, c (Å)9.6745 (3), 13.9432 (6), 23.3654 (10)
V (Å3)3151.8 (2)
Z8
Radiation typeMo Kα
µ (mm−1)0.41
Crystal size (mm)0.45 × 0.35 × 0.10
Data collection
DiffractometerAgilent Xcalibur (Eos, Gemini ultra)
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2014)
Tmin, Tmax0.974, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		16637, 5991, 5182
Rint0.062
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.134, 1.07
No. of reflections5991
No. of parameters376
No. of restraints12
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.73, −0.46
Absolute structureFlack x determined using 1835 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Absolute structure parameter0.03 (5)

Computer programs: CrysAlis PRO (Agilent, 2014), SIR97 (Altomare et al., 1999), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008), SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

 

References

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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 72| Part 5| May 2016| Pages 709-711
doi:10.1107/S2056989016006174
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