research communications
S,3R,8R,10S)-2,2-dichloro-10-hydroxy-3,7,7,10-tetramethyltricyclo[6.4.0.01,3]dodecan-9-one
of (1aLaboratoire 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
The 16H24Cl2O2, 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 i.e. 1S,3R,8R,10S, which is based on the synthetic pathway and further confirmed by [Flack parameter = 0.03 (5)].
of the title compound, CKeywords: crystal structure; α-hydroxyketone; asymmetric synthesis; natural products; absolute configuration; hydrogen bonding.
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). 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 of α-hydroxy has grown significantly (Salvador et al., 2006). In a tentative attempt to prepare new α-hydroxy 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).
2. Structural commentary
There are two molecules (A and B) in the of the title compound, Fig. 1, both having the same the (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.
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 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).
4. Database survey
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).
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) 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 (230–400 mesh) using hexane/ethyl acetate (95:5) as 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 . 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.
details are summarized in Table 2Supporting information
CCDC reference: 1473671
10.1107/S2056989016006174/su5293sup1.cif
contains datablocks I, Global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989016006174/su5293Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989016006174/su5293Isup3.cml
\ 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 of α-hydroxy has grown significantly (Salvador et al., 2006). In a tentative attempt to prepare new α-hydroxy 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 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.
of the title compound, Fig. 1, both having the same the (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 parametersThe 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).
\ 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
(230–400 mesh) using hexane/ethyl acetate (95:5) as 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.Crystal data, data collection and structure
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.\ 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 of α-hydroxy has grown significantly (Salvador et al., 2006). In a tentative attempt to prepare new α-hydroxy 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 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.
of the title compound, Fig. 1, both having the same the (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 parametersThe 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).
\ 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
(230–400 mesh) using hexane/ethyl acetate (95:5) as 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. detailsCrystal data, data collection and structure
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.Data collection: CrysAlis PRO (Agilent, 2014); cell
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).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. | |
Fig. 2. A view showing the disorder (dashed double lines) in molecule B. | |
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. |
C16H24Cl2O2 | Dx = 1.346 Mg m−3 |
Mr = 319.25 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 6322 reflections |
a = 9.6745 (3) Å | θ = 3.7–27.0° |
b = 13.9432 (6) Å | µ = 0.41 mm−1 |
c = 23.3654 (10) Å | T = 173 K |
V = 3151.8 (2) Å3 | Plate, colourless |
Z = 8 | 0.45 × 0.35 × 0.10 mm |
F(000) = 1360 |
Agilent Xcalibur (Eos, Gemini ultra) diffractometer | 5991 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 5182 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
Detector resolution: 16.1978 pixels mm-1 | θmax = 26.0°, θmin = 3.1° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −15→17 |
Tmin = 0.974, Tmax = 1.000 | l = −28→27 |
16637 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-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 = 1.07 | Δρmax = 0.73 e Å−3 |
5991 reflections | Δρmin = −0.46 e Å−3 |
376 parameters | Absolute structure: Flack x determined using 1835 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
12 restraints | Absolute structure parameter: 0.03 (5) |
C16H24Cl2O2 | V = 3151.8 (2) Å3 |
Mr = 319.25 | Z = 8 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 9.6745 (3) Å | µ = 0.41 mm−1 |
b = 13.9432 (6) Å | T = 173 K |
c = 23.3654 (10) Å | 0.45 × 0.35 × 0.10 mm |
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 = 1.000 | Rint = 0.062 |
16637 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.134 | Δρmax = 0.73 e Å−3 |
S = 1.07 | Δρmin = −0.46 e Å−3 |
5991 reflections | Absolute structure: Flack x determined using 1835 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
376 parameters | Absolute structure parameter: 0.03 (5) |
12 restraints |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.0491 (5) | 0.0997 (4) | 0.40650 (19) | 0.0207 (10) | |
C2 | 0.0427 (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 | −0.2365 | 0.0360 | 0.3286 | 0.033* | |
H4B | −0.0962 | 0.0836 | 0.3061 | 0.033* | |
C5 | −0.2276 (5) | 0.1830 (4) | 0.3446 (2) | 0.0305 (12) | |
H5A | −0.2402 | 0.2114 | 0.3062 | 0.037* | |
H5B | −0.3202 | 0.1764 | 0.3623 | 0.037* | |
C6 | −0.1411 (5) | 0.2509 (4) | 0.3809 (2) | 0.0284 (12) | |
H6A | −0.1397 | 0.2251 | 0.4204 | 0.034* | |
H6B | −0.1903 | 0.3131 | 0.3824 | 0.034* | |
C7 | 0.0096 (5) | 0.2716 (3) | 0.3636 (2) | 0.0226 (11) | |
C8 | 0.0986 (5) | 0.1750 (3) | 0.36409 (19) | 0.0192 (10) | |
H8 | 0.0893 | 0.1460 | 0.3251 | 0.023* | |
C9 | 0.2505 (5) | 0.1979 (4) | 0.3721 (2) | 0.0249 (11) | |
C10 | 0.3245 (5) | 0.1663 (4) | 0.4267 (2) | 0.0315 (12) | |
C11 | 0.2258 (6) | 0.1708 (4) | 0.4777 (2) | 0.0313 (13) | |
H11A | 0.2087 | 0.2390 | 0.4871 | 0.038* | |
H11B | 0.2719 | 0.1412 | 0.5111 | 0.038* | |
C12 | 0.0859 (5) | 0.1211 (4) | 0.46868 (19) | 0.0255 (11) | |
H12A | 0.0861 | 0.0600 | 0.4902 | 0.031* | |
H12B | 0.0126 | 0.1622 | 0.4852 | 0.031* | |
C13 | −0.1889 (5) | 0.0269 (4) | 0.4410 (2) | 0.0353 (13) | |
H13A | −0.2373 | −0.0332 | 0.4327 | 0.053* | |
H13B | −0.2564 | 0.0789 | 0.4451 | 0.053* | |
H13C | −0.1367 | 0.0201 | 0.4767 | 0.053* | |
C14 | 0.0144 (6) | 0.3136 (4) | 0.3030 (2) | 0.0328 (13) | |
H14A | −0.0431 | 0.3714 | 0.3014 | 0.049* | |
H14B | −0.0206 | 0.2662 | 0.2757 | 0.049* | |
H14C | 0.1100 | 0.3302 | 0.2933 | 0.049* | |
C15 | 0.0628 (6) | 0.3474 (4) | 0.4049 (2) | 0.0310 (12) | |
H15A | 0.0163 | 0.4085 | 0.3973 | 0.046* | |
H15B | 0.1627 | 0.3553 | 0.3998 | 0.046* | |
H15C | 0.0438 | 0.3273 | 0.4443 | 0.046* | |
C16 | 0.3835 (6) | 0.0654 (4) | 0.4177 (3) | 0.0396 (14) | |
H16A | 0.4486 | 0.0662 | 0.3856 | 0.059* | |
H16B | 0.3080 | 0.0207 | 0.4093 | 0.059* | |
H16C | 0.4316 | 0.0447 | 0.4525 | 0.059* | |
O9 | 0.3149 (4) | 0.2414 (3) | 0.33530 (17) | 0.0364 (9) | |
O10 | 0.4396 (4) | 0.2273 (3) | 0.4373 (2) | 0.0477 (11) | |
H10 | 0.4380 | 0.2736 | 0.4143 | 0.072* | |
Cl1 | 0.10699 (13) | −0.03802 (9) | 0.31897 (5) | 0.0289 (3) | |
Cl2 | 0.07611 (14) | −0.09878 (9) | 0.43518 (6) | 0.0331 (3) | |
C1A | 0.6252 (5) | 0.6364 (4) | 0.3446 (2) | 0.0236 (11) | |
C2A | 0.7685 (5) | 0.6191 (4) | 0.3695 (2) | 0.0249 (11) | |
C3A | 0.7087 (5) | 0.7175 (4) | 0.3728 (2) | 0.0235 (11) | |
C4A | 0.6605 (6) | 0.7556 (4) | 0.4303 (2) | 0.0332 (12) | |
H4A1 | 0.6504 | 0.7010 | 0.4571 | 0.040* | |
H4A2 | 0.7327 | 0.7986 | 0.4459 | 0.040* | |
C5A | 0.5252 (6) | 0.8098 (4) | 0.4280 (3) | 0.0408 (14) | 0.54 |
H5A1 | 0.5457 | 0.8791 | 0.4241 | 0.049* | 0.54 |
H5A2 | 0.4764 | 0.8007 | 0.4649 | 0.049* | 0.54 |
C6A | 0.4225 (9) | 0.7787 (6) | 0.3768 (4) | 0.0322 (18) | 0.54 |
H6A1 | 0.3403 | 0.8210 | 0.3771 | 0.039* | 0.54 |
H6A2 | 0.4702 | 0.7874 | 0.3397 | 0.039* | 0.54 |
C7A | 0.3742 (5) | 0.6705 (4) | 0.3827 (2) | 0.0373 (14) | 0.54 |
C14A | 0.2879 (11) | 0.6532 (10) | 0.4336 (4) | 0.0436 (17) | 0.54 |
H14D | 0.2193 | 0.7046 | 0.4372 | 0.065* | 0.54 |
H14E | 0.3464 | 0.6521 | 0.4678 | 0.065* | 0.54 |
H14F | 0.2404 | 0.5914 | 0.4297 | 0.065* | 0.54 |
C15A | 0.2798 (10) | 0.6644 (10) | 0.3284 (4) | 0.0436 (17) | 0.54 |
H15D | 0.2465 | 0.5985 | 0.3237 | 0.065* | 0.54 |
H15E | 0.3329 | 0.6832 | 0.2945 | 0.065* | 0.54 |
H15F | 0.2007 | 0.7076 | 0.3330 | 0.065* | 0.54 |
C8A | 0.5004 (5) | 0.5996 (4) | 0.3788 (2) | 0.0241 (11) | |
H8A | 0.5341 | 0.5913 | 0.4189 | 0.029* | |
C5B | 0.5252 (6) | 0.8098 (4) | 0.4280 (3) | 0.0408 (14) | 0.46 |
H5B1 | 0.5135 | 0.8403 | 0.3900 | 0.049* | 0.46 |
H5B2 | 0.5237 | 0.8606 | 0.4576 | 0.049* | 0.46 |
C6B | 0.4056 (10) | 0.7356 (7) | 0.4391 (4) | 0.0322 (18) | 0.46 |
H6B1 | 0.3206 | 0.7706 | 0.4501 | 0.039* | 0.46 |
H6B2 | 0.4316 | 0.6933 | 0.4713 | 0.039* | 0.46 |
C7B | 0.3742 (5) | 0.6705 (4) | 0.3827 (2) | 0.0373 (14) | 0.46 |
C14B | 0.2512 (11) | 0.6156 (11) | 0.4076 (6) | 0.0436 (17) | 0.46 |
H14G | 0.1848 | 0.6612 | 0.4238 | 0.065* | 0.46 |
H14H | 0.2836 | 0.5722 | 0.4377 | 0.065* | 0.46 |
H14I | 0.2065 | 0.5784 | 0.3773 | 0.065* | 0.46 |
C15B | 0.3436 (13) | 0.7365 (10) | 0.3366 (5) | 0.0436 (17) | 0.46 |
H15G | 0.3090 | 0.7006 | 0.3035 | 0.065* | 0.46 |
H15H | 0.4278 | 0.7711 | 0.3259 | 0.065* | 0.46 |
H15I | 0.2731 | 0.7824 | 0.3492 | 0.065* | 0.46 |
C9A | 0.4633 (5) | 0.4997 (4) | 0.3580 (2) | 0.0308 (13) | |
C10A | 0.4967 (6) | 0.4694 (4) | 0.2964 (2) | 0.0347 (13) | |
C11A | 0.5131 (8) | 0.5565 (5) | 0.2563 (3) | 0.0525 (17) | |
H11C | 0.5499 | 0.5342 | 0.2190 | 0.063* | |
H11D | 0.4209 | 0.5850 | 0.2492 | 0.063* | |
C12A | 0.6092 (6) | 0.6342 (4) | 0.2801 (2) | 0.0316 (12) | |
H12C | 0.7019 | 0.6253 | 0.2629 | 0.038* | |
H12D | 0.5743 | 0.6974 | 0.2675 | 0.038* | |
C13A | 0.7716 (6) | 0.7959 (4) | 0.3355 (2) | 0.0378 (14) | |
H13D | 0.8584 | 0.8179 | 0.3527 | 0.057* | |
H13E | 0.7070 | 0.8498 | 0.3328 | 0.057* | |
H13F | 0.7898 | 0.7704 | 0.2972 | 0.057* | |
C16A | 0.6231 (7) | 0.4100 (5) | 0.2982 (3) | 0.0505 (17) | |
H16D | 0.6034 | 0.3497 | 0.3182 | 0.076* | |
H16E | 0.6962 | 0.4447 | 0.3186 | 0.076* | |
H16F | 0.6536 | 0.3961 | 0.2591 | 0.076* | |
O9A | 0.4112 (5) | 0.4425 (3) | 0.3907 (2) | 0.0612 (14) | |
O10A | 0.3816 (5) | 0.4186 (4) | 0.2726 (2) | 0.0631 (14) | |
H10A | 0.3630 | 0.3711 | 0.2933 | 0.095* | |
Cl1A | 0.91022 (13) | 0.59664 (11) | 0.32401 (6) | 0.0384 (3) | |
Cl2A | 0.78988 (13) | 0.54934 (10) | 0.43211 (6) | 0.0347 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.024 (2) | 0.022 (2) | 0.016 (2) | 0.003 (2) | −0.0005 (18) | −0.005 (2) |
C2 | 0.028 (2) | 0.019 (2) | 0.021 (2) | −0.001 (2) | 0.003 (2) | 0.001 (2) |
C3 | 0.025 (2) | 0.019 (2) | 0.028 (2) | 0.000 (2) | 0.002 (2) | 0.003 (2) |
C4 | 0.024 (2) | 0.025 (3) | 0.033 (3) | −0.003 (2) | −0.007 (2) | −0.005 (2) |
C5 | 0.026 (2) | 0.029 (3) | 0.037 (3) | 0.005 (2) | −0.004 (2) | 0.005 (3) |
C6 | 0.034 (3) | 0.026 (3) | 0.025 (3) | 0.005 (2) | 0.002 (2) | 0.000 (2) |
C7 | 0.030 (2) | 0.013 (2) | 0.025 (3) | 0.000 (2) | 0.004 (2) | 0.001 (2) |
C8 | 0.025 (2) | 0.016 (2) | 0.017 (2) | 0.003 (2) | 0.0004 (19) | −0.004 (2) |
C9 | 0.027 (3) | 0.021 (3) | 0.026 (3) | 0.002 (2) | 0.003 (2) | −0.010 (2) |
C10 | 0.024 (2) | 0.037 (3) | 0.034 (3) | −0.003 (2) | −0.009 (2) | −0.008 (3) |
C11 | 0.041 (3) | 0.029 (3) | 0.023 (3) | 0.004 (3) | −0.012 (2) | −0.005 (2) |
C12 | 0.033 (3) | 0.029 (3) | 0.015 (2) | 0.007 (3) | 0.000 (2) | −0.002 (2) |
C13 | 0.030 (3) | 0.032 (3) | 0.044 (3) | 0.001 (2) | 0.010 (2) | 0.004 (3) |
C14 | 0.042 (3) | 0.029 (3) | 0.028 (3) | 0.008 (3) | 0.005 (2) | 0.005 (3) |
C15 | 0.033 (3) | 0.025 (3) | 0.035 (3) | 0.006 (2) | 0.003 (2) | −0.004 (2) |
C16 | 0.032 (3) | 0.035 (3) | 0.051 (4) | 0.008 (3) | −0.013 (3) | −0.003 (3) |
O9 | 0.0342 (19) | 0.030 (2) | 0.045 (2) | −0.0094 (18) | 0.0140 (18) | −0.0039 (19) |
O10 | 0.038 (2) | 0.044 (2) | 0.062 (3) | −0.011 (2) | −0.016 (2) | −0.008 (2) |
Cl1 | 0.0373 (7) | 0.0254 (6) | 0.0241 (6) | 0.0032 (6) | 0.0005 (5) | −0.0078 (6) |
Cl2 | 0.0416 (7) | 0.0243 (6) | 0.0334 (7) | 0.0054 (6) | −0.0017 (6) | 0.0071 (6) |
C1A | 0.024 (2) | 0.024 (3) | 0.023 (3) | −0.003 (2) | 0.002 (2) | −0.002 (2) |
C2A | 0.022 (2) | 0.027 (3) | 0.026 (3) | 0.001 (2) | −0.001 (2) | 0.001 (2) |
C3A | 0.025 (2) | 0.019 (2) | 0.026 (3) | −0.001 (2) | −0.004 (2) | 0.003 (2) |
C4A | 0.048 (3) | 0.022 (3) | 0.029 (3) | −0.003 (2) | −0.003 (3) | 0.002 (2) |
C5A | 0.044 (3) | 0.027 (3) | 0.052 (4) | 0.003 (3) | 0.005 (3) | −0.012 (3) |
C6A | 0.031 (4) | 0.033 (4) | 0.032 (4) | 0.010 (4) | 0.000 (3) | 0.005 (4) |
C7A | 0.025 (3) | 0.036 (3) | 0.050 (4) | 0.005 (3) | 0.002 (3) | −0.002 (3) |
C14A | 0.030 (3) | 0.060 (5) | 0.040 (4) | 0.015 (3) | 0.008 (3) | 0.009 (4) |
C15A | 0.030 (3) | 0.060 (5) | 0.040 (4) | 0.015 (3) | 0.008 (3) | 0.009 (4) |
C8A | 0.022 (2) | 0.022 (3) | 0.028 (3) | 0.000 (2) | 0.000 (2) | −0.001 (2) |
C5B | 0.044 (3) | 0.027 (3) | 0.052 (4) | 0.003 (3) | 0.005 (3) | −0.012 (3) |
C6B | 0.031 (4) | 0.033 (4) | 0.032 (4) | 0.010 (4) | 0.000 (3) | 0.005 (4) |
C7B | 0.025 (3) | 0.036 (3) | 0.050 (4) | 0.005 (3) | 0.002 (3) | −0.002 (3) |
C14B | 0.030 (3) | 0.060 (5) | 0.040 (4) | 0.015 (3) | 0.008 (3) | 0.009 (4) |
C15B | 0.030 (3) | 0.060 (5) | 0.040 (4) | 0.015 (3) | 0.008 (3) | 0.009 (4) |
C9A | 0.025 (3) | 0.028 (3) | 0.040 (3) | −0.004 (2) | 0.005 (2) | −0.005 (3) |
C10A | 0.040 (3) | 0.033 (3) | 0.031 (3) | −0.008 (3) | −0.009 (2) | −0.010 (3) |
C11A | 0.063 (4) | 0.048 (4) | 0.046 (4) | −0.009 (4) | −0.021 (3) | 0.004 (3) |
C12A | 0.035 (3) | 0.036 (3) | 0.024 (3) | −0.008 (3) | 0.001 (2) | −0.004 (2) |
C13A | 0.040 (3) | 0.032 (3) | 0.041 (3) | −0.012 (3) | −0.002 (3) | 0.011 (3) |
C16A | 0.065 (4) | 0.047 (4) | 0.040 (3) | 0.011 (4) | 0.000 (3) | −0.013 (3) |
O9A | 0.077 (3) | 0.043 (3) | 0.064 (3) | −0.033 (3) | 0.043 (3) | −0.012 (2) |
O10A | 0.065 (3) | 0.065 (3) | 0.059 (3) | −0.025 (3) | −0.032 (3) | 0.002 (3) |
Cl1A | 0.0246 (6) | 0.0456 (8) | 0.0450 (8) | 0.0026 (6) | 0.0110 (6) | 0.0044 (7) |
Cl2A | 0.0345 (6) | 0.0351 (7) | 0.0345 (7) | 0.0095 (6) | 0.0003 (6) | 0.0135 (6) |
C1—C8 | 1.521 (7) | C3A—C13A | 1.523 (7) |
C1—C2 | 1.521 (7) | C4A—C5B | 1.513 (8) |
C1—C12 | 1.525 (6) | C4A—C5A | 1.513 (8) |
C1—C3 | 1.547 (7) | C4A—H4A1 | 0.9900 |
C2—C3 | 1.493 (7) | C4A—H4A2 | 0.9900 |
C2—Cl1 | 1.764 (5) | C5A—C6A | 1.614 (8) |
C2—Cl2 | 1.770 (5) | C5A—H5A1 | 0.9900 |
C3—C4 | 1.515 (7) | C5A—H5A2 | 0.9900 |
C3—C13 | 1.529 (7) | C6A—C7A | 1.586 (8) |
C4—C5 | 1.539 (7) | C6A—H6A1 | 0.9900 |
C4—H4A | 0.9900 | C6A—H6A2 | 0.9900 |
C4—H4B | 0.9900 | C7A—C14A | 1.473 (9) |
C5—C6 | 1.522 (7) | C7A—C15A | 1.566 (9) |
C5—H5A | 0.9900 | C7A—C8A | 1.574 (7) |
C5—H5B | 0.9900 | C14A—H14D | 0.9800 |
C6—C7 | 1.540 (7) | C14A—H14E | 0.9800 |
C6—H6A | 0.9900 | C14A—H14F | 0.9800 |
C6—H6B | 0.9900 | C15A—H15D | 0.9800 |
C7—C15 | 1.523 (7) | C15A—H15E | 0.9800 |
C7—C14 | 1.532 (7) | C15A—H15F | 0.9800 |
C7—C8 | 1.599 (6) | C8A—C9A | 1.517 (7) |
C8—C9 | 1.515 (7) | C8A—C7B | 1.574 (7) |
C8—H8 | 1.0000 | C8A—H8A | 1.0000 |
C9—O9 | 1.222 (6) | C5B—C6B | 1.574 (9) |
C9—C10 | 1.528 (7) | C5B—H5B1 | 0.9900 |
C10—O10 | 1.422 (6) | C5B—H5B2 | 0.9900 |
C10—C11 | 1.528 (8) | C6B—C7B | 1.628 (9) |
C10—C16 | 1.533 (8) | C6B—H6B1 | 0.9900 |
C11—C12 | 1.536 (7) | C6B—H6B2 | 0.9900 |
C11—H11A | 0.9900 | C7B—C15B | 1.448 (10) |
C11—H11B | 0.9900 | C7B—C14B | 1.529 (10) |
C12—H12A | 0.9900 | C14B—H14G | 0.9800 |
C12—H12B | 0.9900 | C14B—H14H | 0.9800 |
C13—H13A | 0.9800 | C14B—H14I | 0.9800 |
C13—H13B | 0.9800 | C15B—H15G | 0.9800 |
C13—H13C | 0.9800 | C15B—H15H | 0.9800 |
C14—H14A | 0.9800 | C15B—H15I | 0.9800 |
C14—H14B | 0.9800 | C9A—O9A | 1.214 (7) |
C14—H14C | 0.9800 | C9A—C10A | 1.535 (8) |
C15—H15A | 0.9800 | C10A—O10A | 1.432 (6) |
C15—H15B | 0.9800 | C10A—C16A | 1.478 (8) |
C15—H15C | 0.9800 | C10A—C11A | 1.543 (9) |
C16—H16A | 0.9800 | C11A—C12A | 1.532 (8) |
C16—H16B | 0.9800 | C11A—H11C | 0.9900 |
C16—H16C | 0.9800 | C11A—H11D | 0.9900 |
O10—H10 | 0.8400 | C12A—H12C | 0.9900 |
C1A—C12A | 1.515 (7) | C12A—H12D | 0.9900 |
C1A—C2A | 1.522 (7) | C13A—H13D | 0.9800 |
C1A—C8A | 1.535 (7) | C13A—H13E | 0.9800 |
C1A—C3A | 1.537 (7) | C13A—H13F | 0.9800 |
C2A—C3A | 1.491 (7) | C16A—H16D | 0.9800 |
C2A—Cl1A | 1.763 (5) | C16A—H16E | 0.9800 |
C2A—Cl2A | 1.769 (5) | C16A—H16F | 0.9800 |
C3A—C4A | 1.520 (7) | O10A—H10A | 0.8400 |
C8—C1—C2 | 118.1 (4) | C13A—C3A—C1A | 119.6 (4) |
C8—C1—C12 | 114.4 (4) | C5B—C4A—C3A | 114.1 (5) |
C2—C1—C12 | 119.1 (4) | C5A—C4A—C3A | 114.1 (5) |
C8—C1—C3 | 116.1 (4) | C5A—C4A—H4A1 | 108.7 |
C2—C1—C3 | 58.2 (3) | C3A—C4A—H4A1 | 108.7 |
C12—C1—C3 | 119.8 (4) | C5A—C4A—H4A2 | 108.7 |
C3—C2—C1 | 61.8 (3) | C3A—C4A—H4A2 | 108.7 |
C3—C2—Cl1 | 121.0 (4) | H4A1—C4A—H4A2 | 107.6 |
C1—C2—Cl1 | 121.0 (3) | C4A—C5A—C6A | 115.2 (5) |
C3—C2—Cl2 | 118.7 (3) | C4A—C5A—H5A1 | 108.5 |
C1—C2—Cl2 | 120.5 (4) | C6A—C5A—H5A1 | 108.5 |
Cl1—C2—Cl2 | 108.0 (3) | C4A—C5A—H5A2 | 108.5 |
C2—C3—C4 | 118.9 (4) | C6A—C5A—H5A2 | 108.5 |
C2—C3—C13 | 119.6 (4) | H5A1—C5A—H5A2 | 107.5 |
C4—C3—C13 | 113.1 (4) | C7A—C6A—C5A | 111.9 (6) |
C2—C3—C1 | 60.0 (3) | C7A—C6A—H6A1 | 109.2 |
C4—C3—C1 | 117.0 (4) | C5A—C6A—H6A1 | 109.2 |
C13—C3—C1 | 118.5 (4) | C7A—C6A—H6A2 | 109.2 |
C3—C4—C5 | 112.3 (4) | C5A—C6A—H6A2 | 109.2 |
C3—C4—H4A | 109.1 | H6A1—C6A—H6A2 | 107.9 |
C5—C4—H4A | 109.1 | C14A—C7A—C15A | 108.3 (7) |
C3—C4—H4B | 109.1 | C14A—C7A—C8A | 112.6 (6) |
C5—C4—H4B | 109.1 | C15A—C7A—C8A | 111.8 (5) |
H4A—C4—H4B | 107.9 | C14A—C7A—C6A | 113.1 (7) |
C6—C5—C4 | 113.4 (4) | C15A—C7A—C6A | 98.8 (6) |
C6—C5—H5A | 108.9 | C8A—C7A—C6A | 111.4 (5) |
C4—C5—H5A | 108.9 | C7A—C14A—H14D | 109.5 |
C6—C5—H5B | 108.9 | C7A—C14A—H14E | 109.5 |
C4—C5—H5B | 108.9 | H14D—C14A—H14E | 109.5 |
H5A—C5—H5B | 107.7 | C7A—C14A—H14F | 109.5 |
C5—C6—C7 | 119.4 (4) | H14D—C14A—H14F | 109.5 |
C5—C6—H6A | 107.5 | H14E—C14A—H14F | 109.5 |
C7—C6—H6A | 107.5 | C7A—C15A—H15D | 109.5 |
C5—C6—H6B | 107.5 | C7A—C15A—H15E | 109.5 |
C7—C6—H6B | 107.5 | H15D—C15A—H15E | 109.5 |
H6A—C6—H6B | 107.0 | C7A—C15A—H15F | 109.5 |
C15—C7—C14 | 108.1 (4) | H15D—C15A—H15F | 109.5 |
C15—C7—C6 | 106.5 (4) | H15E—C15A—H15F | 109.5 |
C14—C7—C6 | 110.1 (4) | C9A—C8A—C1A | 109.1 (4) |
C15—C7—C8 | 113.4 (4) | C9A—C8A—C7A | 114.3 (4) |
C14—C7—C8 | 108.2 (4) | C1A—C8A—C7A | 115.5 (4) |
C6—C7—C8 | 110.5 (4) | C9A—C8A—C7B | 114.3 (4) |
C9—C8—C1 | 111.8 (4) | C1A—C8A—C7B | 115.5 (4) |
C9—C8—C7 | 110.3 (4) | C9A—C8A—H8A | 105.7 |
C1—C8—C7 | 114.6 (4) | C1A—C8A—H8A | 105.7 |
C9—C8—H8 | 106.6 | C7A—C8A—H8A | 105.7 |
C1—C8—H8 | 106.6 | C4A—C5B—C6B | 107.6 (6) |
C7—C8—H8 | 106.6 | C4A—C5B—H5B1 | 110.2 |
O9—C9—C8 | 120.8 (5) | C6B—C5B—H5B1 | 110.2 |
O9—C9—C10 | 119.4 (4) | C4A—C5B—H5B2 | 110.2 |
C8—C9—C10 | 119.8 (4) | C6B—C5B—H5B2 | 110.2 |
O10—C10—C9 | 109.9 (5) | H5B1—C5B—H5B2 | 108.5 |
O10—C10—C11 | 109.2 (4) | C5B—C6B—C7B | 111.8 (6) |
C9—C10—C11 | 110.3 (4) | C5B—C6B—H6B1 | 109.3 |
O10—C10—C16 | 106.4 (4) | C7B—C6B—H6B1 | 109.3 |
C9—C10—C16 | 108.9 (4) | C5B—C6B—H6B2 | 109.3 |
C11—C10—C16 | 112.1 (5) | C7B—C6B—H6B2 | 109.3 |
C10—C11—C12 | 115.2 (4) | H6B1—C6B—H6B2 | 107.9 |
C10—C11—H11A | 108.5 | C15B—C7B—C14B | 116.2 (8) |
C12—C11—H11A | 108.5 | C15B—C7B—C8A | 121.0 (6) |
C10—C11—H11B | 108.5 | C14B—C7B—C8A | 108.2 (6) |
C12—C11—H11B | 108.5 | C15B—C7B—C6B | 106.6 (8) |
H11A—C11—H11B | 107.5 | C14B—C7B—C6B | 96.7 (7) |
C1—C12—C11 | 115.1 (4) | C8A—C7B—C6B | 104.7 (5) |
C1—C12—H12A | 108.5 | C7B—C14B—H14G | 109.5 |
C11—C12—H12A | 108.5 | C7B—C14B—H14H | 109.5 |
C1—C12—H12B | 108.5 | H14G—C14B—H14H | 109.5 |
C11—C12—H12B | 108.5 | C7B—C14B—H14I | 109.5 |
H12A—C12—H12B | 107.5 | H14G—C14B—H14I | 109.5 |
C3—C13—H13A | 109.5 | H14H—C14B—H14I | 109.5 |
C3—C13—H13B | 109.5 | C7B—C15B—H15G | 109.5 |
H13A—C13—H13B | 109.5 | C7B—C15B—H15H | 109.5 |
C3—C13—H13C | 109.5 | H15G—C15B—H15H | 109.5 |
H13A—C13—H13C | 109.5 | C7B—C15B—H15I | 109.5 |
H13B—C13—H13C | 109.5 | H15G—C15B—H15I | 109.5 |
C7—C14—H14A | 109.5 | H15H—C15B—H15I | 109.5 |
C7—C14—H14B | 109.5 | O9A—C9A—C8A | 120.1 (5) |
H14A—C14—H14B | 109.5 | O9A—C9A—C10A | 119.7 (5) |
C7—C14—H14C | 109.5 | C8A—C9A—C10A | 120.2 (5) |
H14A—C14—H14C | 109.5 | O10A—C10A—C16A | 112.2 (5) |
H14B—C14—H14C | 109.5 | O10A—C10A—C9A | 109.7 (5) |
C7—C15—H15A | 109.5 | C16A—C10A—C9A | 107.6 (5) |
C7—C15—H15B | 109.5 | O10A—C10A—C11A | 103.4 (5) |
H15A—C15—H15B | 109.5 | C16A—C10A—C11A | 111.9 (6) |
C7—C15—H15C | 109.5 | C9A—C10A—C11A | 112.0 (5) |
H15A—C15—H15C | 109.5 | C12A—C11A—C10A | 113.4 (5) |
H15B—C15—H15C | 109.5 | C12A—C11A—H11C | 108.9 |
C10—C16—H16A | 109.5 | C10A—C11A—H11C | 108.9 |
C10—C16—H16B | 109.5 | C12A—C11A—H11D | 108.9 |
H16A—C16—H16B | 109.5 | C10A—C11A—H11D | 108.9 |
C10—C16—H16C | 109.5 | H11C—C11A—H11D | 107.7 |
H16A—C16—H16C | 109.5 | C1A—C12A—C11A | 116.0 (5) |
H16B—C16—H16C | 109.5 | C1A—C12A—H12C | 108.3 |
C10—O10—H10 | 109.5 | C11A—C12A—H12C | 108.3 |
C12A—C1A—C2A | 118.0 (4) | C1A—C12A—H12D | 108.3 |
C12A—C1A—C8A | 115.4 (4) | C11A—C12A—H12D | 108.3 |
C2A—C1A—C8A | 117.7 (4) | H12C—C12A—H12D | 107.4 |
C12A—C1A—C3A | 119.6 (4) | C3A—C13A—H13D | 109.5 |
C2A—C1A—C3A | 58.4 (3) | C3A—C13A—H13E | 109.5 |
C8A—C1A—C3A | 115.9 (4) | H13D—C13A—H13E | 109.5 |
C3A—C2A—C1A | 61.4 (3) | C3A—C13A—H13F | 109.5 |
C3A—C2A—Cl1A | 119.7 (4) | H13D—C13A—H13F | 109.5 |
C1A—C2A—Cl1A | 120.5 (4) | H13E—C13A—H13F | 109.5 |
C3A—C2A—Cl2A | 120.6 (4) | C10A—C16A—H16D | 109.5 |
C1A—C2A—Cl2A | 120.6 (4) | C10A—C16A—H16E | 109.5 |
Cl1A—C2A—Cl2A | 108.0 (3) | H16D—C16A—H16E | 109.5 |
C2A—C3A—C4A | 119.1 (4) | C10A—C16A—H16F | 109.5 |
C2A—C3A—C13A | 118.4 (4) | H16D—C16A—H16F | 109.5 |
C4A—C3A—C13A | 112.2 (4) | H16E—C16A—H16F | 109.5 |
C2A—C3A—C1A | 60.3 (3) | C10A—O10A—H10A | 109.5 |
C4A—C3A—C1A | 118.3 (4) |
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−1/2, −y+1/2, −z+1. |
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−1/2, −y+1/2, −z+1. |
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) |
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) |
Absolute structure parameter | 0.03 (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).
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