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The crystal and molecular structure of the title compound, C19H20Cl2O2, reveals a chair conformation for the pyran ring in which the hydroxyl group is axially oriented. All the other substituents occupy equatorial positions. There are two molecules in the asymmetric unit.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802023310/ob6197sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802023310/ob6197Isup2.hkl
Contains datablock I

CCDC reference: 204669

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.053
  • wR factor = 0.146
  • Data-to-parameter ratio = 15.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
ABSTM_02 Alert B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.650 0.998 Tmin' and Tmax expected: 0.928 0.965 RR' = 0.676 Please check that your absorption correction is appropriate.
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
0 Alert Level C = Please check

Comment top

Pyran derivatives are important constituents of many vitamin derivatives and antiulcer drugs, such as alpha tocopheral (vitamin E) (Finar, 1989) and methantheline (Parimoo, 1999). Persubstituted pyrans are easily synthesized, and their ring conformations would serve as comparative models for their cyclohexane counterparts. Molecules with a pyran ring can assume planar (Kumar et al., 1999), twist boat (Usman et al., 2002), sofa (Ray et al., 1998) and chair (Belakhov et al., 2002) conformations depending upon the level of unsaturation and the nature of the substituents on the ring. This investigation was undertaken to assign the conformation of the pyran ring and the orientation of the hydroxyl group in the title molecule, (I).

There are two molecules in the asymmetric unit of (I). The pyran rings are in chair conformations, as shown in Fig. 1. The torsion angles around the bonds involving the ring atoms deviate from the value of 56° expected for a perfect chair conformation (Kalsi, 1997). The bond lengths within the pyran ring are in the range 1.425 (3)—1.540 (4) Å (for molecule 1 containing O1 atom) and 1.447 (3)—1.540 (3) Å (for molecule 2 containing O1A atom). The ranges of bond angles are 108.56 (19)–114.78 (18)° (for molecule 1) and 107.4 (2)–112.57 (17)° (for molecule 2). The configurations of chiral atoms C2, C3, C5 and C6 in molecule 1 are found to be S, S, S and R, respectively, which are identical to those of their counterparts in molecule 2. However, the compound crystallizes as a racemic mixture in the corresponding space group P21/c. The relative orientation of the two chlorophenyl groups differ in the two molecules, as shown by the dihedral angles between the two rings of 44.01 (1)° in molecule 1 and 51.01 (1)° in molecule 2. The equatorial orientations of all substituents except the hydroxyl groups are confirmed by the torsion angles of about 180° comprising the external atom and the other three ring atoms as observed in the pentasubstituted cyclohexan-1-one derivative (Sarangarajan et al., 2002). The hydroxyl groups are oriented axially, as confirmed by the average of the C7—C3—C4—O8 torsion angles of 61.85 (3)°, which is close to the ideal value of 60° (Nasipuri, 1992).

In the crystal structure, the molecules are assembled in layers. The adjacent layers interact through O—H···O intermolecular hydrogen bonding involving atoms O8 and O1A(1 − x, 1/2 + y, 1/2 − z) at a distance of 2.850 (3) Å with an angle of 163 (3)° around atom H8. This is supplemented by another interaction between O8A and O8(x, 3/2 − y, 1/2 + z) at a distance of 2.833 (3) Å with an angle of 152 (3)° around atom H8A (Fig. 2 and Table 2).

Experimental top

The title compound, (I), was obtained by the reduction of tetrahydropyran-4-one with aluminium isopropoxide in propan-2-ol. The white solid was seperated by chromatography over silica gel and eluted with a hexane–dichloromethane mixture (1:10). Diffraction quality crystals of (I) were obtained by recrystallization from a dichloromethane–hexane mixture.

Refinement top

The H atoms of the hydroxyl groups were located from a difference Fourier map and their positions refined. The O—H distances were computed to be 0.84 (4) and 0.81 (3) Å. H atoms attached to C atoms were included in calculated positions, with displacement parameters fixed at 1.2 Ueq of their carrier atoms. The displacement paramaters of the H atoms of both the hydroxyl groups were fixed at 1.5Ueq of the respective O atoms during the refinement.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. ORTEP plot of the molecule, ellipsoids at the 30% probability level. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. Packing diagram showing the layer structure formed by the intermolecular association of molecules via hydrogen bonds.
r-2,c-6-bis(4-chlorophenyl)-3,5-dimethyltetrahydropyran-t-4-ol top
Crystal data top
C19H20Cl2O2Least Squares Treatment of 25 SET4 setting angles.
Mr = 351.25Dx = 1.273 Mg m3
Monoclinic, P21/cMelting point = 385–387 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71069 Å
a = 12.1315 (9) ÅCell parameters from 25 reflections
b = 11.7075 (19) Åθ = 2–12°
c = 26.177 (3) ŵ = 0.36 mm1
β = 99.728 (9)°T = 298 K
V = 3664.4 (8) Å3Plate, colourless
Z = 80.2 × 0.2 × 0.1 mm
F(000) = 1472
Data collection top
Enraf-Nonius CAD-4
diffractometer
6670 independent reflections
Radiation source: Rotating Anode5034 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 18.4 pixels mm-1θmax = 25.3°, θmin = 1.6°
ω–2θ scansh = 014
Absorption correction: ψ scan
(North et al., 1968)
k = 014
Tmin = 0.650, Tmax = 0.999l = 3131
7004 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.146 w = 1/[σ2(Fo2) + (0.059P)2 + 2.0872P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
6670 reflectionsΔρmax = 0.50 e Å3
423 parametersΔρmin = 0.42 e Å3
0 restraintsExtinction correction: SHELXL, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0046 (5)
Crystal data top
C19H20Cl2O2V = 3664.4 (8) Å3
Mr = 351.25Z = 8
Monoclinic, P21/cMo Kα radiation
a = 12.1315 (9) ŵ = 0.36 mm1
b = 11.7075 (19) ÅT = 298 K
c = 26.177 (3) Å0.2 × 0.2 × 0.1 mm
β = 99.728 (9)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
6670 independent reflections
Absorption correction: ψ scan
(North et al., 1968)
5034 reflections with I > 2σ(I)
Tmin = 0.650, Tmax = 0.999Rint = 0.027
7004 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.146H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.50 e Å3
6670 reflectionsΔρmin = 0.42 e Å3
423 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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. The asymmetric unit of the cell consists of two molecules with a total number of forty six non-hydrogen atoms which were anisotropically refined using the atomic scattering factors given in SHELX97 program. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.02403 (7)0.24421 (7)0.04077 (4)0.0910 (3)
Cl20.15982 (8)1.11554 (10)0.23664 (4)0.1022 (4)
O10.14094 (14)0.75809 (15)0.12199 (7)0.0593 (6)
O80.40284 (16)0.84165 (17)0.10508 (7)0.0621 (6)
C20.2128 (2)0.6886 (2)0.09728 (10)0.0538 (8)
C30.3254 (2)0.6690 (2)0.13324 (10)0.0556 (8)
C40.3763 (2)0.7852 (2)0.15023 (9)0.0549 (8)
C50.2959 (2)0.8563 (2)0.17540 (10)0.0564 (8)
C60.1848 (2)0.8685 (2)0.13763 (10)0.0569 (8)
C70.4056 (2)0.5941 (3)0.10994 (13)0.0743 (11)
C90.3463 (3)0.9709 (3)0.19462 (12)0.0735 (11)
C100.1512 (2)0.5784 (2)0.08245 (10)0.0537 (8)
C110.1649 (2)0.5199 (2)0.03837 (10)0.0580 (9)
C120.1122 (2)0.4166 (2)0.02515 (11)0.0621 (9)
C130.0444 (2)0.3728 (2)0.05701 (12)0.0622 (9)
C140.0273 (2)0.4293 (3)0.10073 (13)0.0723 (11)
C150.0809 (2)0.5322 (3)0.11344 (12)0.0686 (10)
C160.0964 (2)0.9299 (2)0.16086 (10)0.0588 (9)
C170.0759 (3)1.0454 (3)0.15234 (14)0.0817 (11)
C180.0018 (3)1.1027 (3)0.17596 (15)0.0875 (15)
C190.0600 (2)1.0448 (3)0.20757 (12)0.0715 (11)
C200.0434 (3)0.9301 (3)0.21627 (12)0.0734 (11)
C210.0344 (2)0.8741 (3)0.19265 (12)0.0689 (10)
Cl1A0.22632 (11)0.05643 (9)0.32117 (5)0.1159 (5)
Cl2A0.67787 (10)0.87250 (9)0.28889 (4)0.1027 (4)
O1A0.39797 (14)0.47094 (14)0.39463 (6)0.0520 (6)
O8A0.32641 (19)0.53403 (18)0.51305 (7)0.0702 (7)
C2A0.3376 (2)0.3978 (2)0.42491 (9)0.0516 (8)
C3A0.2300 (2)0.4586 (2)0.43397 (10)0.0603 (9)
C4A0.2649 (2)0.5679 (2)0.46384 (10)0.0634 (9)
C5A0.3338 (2)0.6438 (2)0.43421 (10)0.0599 (9)
C6A0.4338 (2)0.5766 (2)0.42098 (9)0.0519 (8)
C7A0.1525 (3)0.3855 (3)0.46030 (13)0.0795 (11)
C9A0.3719 (3)0.7534 (3)0.46327 (13)0.0855 (13)
C10A0.3156 (2)0.2847 (2)0.39789 (10)0.0554 (8)
C11A0.3178 (3)0.1855 (3)0.42650 (11)0.0676 (10)
C12A0.2899 (3)0.0807 (3)0.40329 (13)0.0768 (11)
C13A0.2615 (3)0.0753 (3)0.35068 (13)0.0746 (12)
C14A0.2614 (3)0.1718 (3)0.32099 (12)0.0805 (11)
C15A0.2885 (3)0.2760 (3)0.34460 (10)0.0689 (10)
C16A0.4976 (2)0.6448 (2)0.38693 (9)0.0519 (8)
C17A0.6024 (2)0.6884 (2)0.40598 (10)0.0621 (9)
C18A0.6578 (3)0.7581 (3)0.37607 (12)0.0714 (11)
C19A0.6092 (3)0.7834 (2)0.32650 (11)0.0688 (10)
C20A0.5064 (3)0.7400 (3)0.30615 (11)0.0750 (11)
C21A0.4512 (2)0.6711 (3)0.33634 (10)0.0669 (10)
H20.226500.727200.065700.0650*
H30.309400.630200.164300.0670*
H40.445200.773500.175200.0660*
H50.280400.814000.205700.0680*
H60.198300.910400.106900.0680*
H80.463 (3)0.878 (3)0.1121 (14)0.1010*
H110.210900.550700.016800.0700*
H120.122800.377900.004700.0750*
H140.020000.398800.121700.0870*
H150.069400.570800.143200.0820*
H170.115101.085200.130400.0980*
H180.014001.180400.170200.1050*
H200.083900.890600.237800.0880*
H210.045400.796300.198400.0830*
H710.473400.584700.134500.1110*
H720.422400.629400.079000.1110*
H730.372000.520800.101500.1110*
H910.293001.013100.210400.1100*
H920.364901.013500.165900.1100*
H930.412600.958300.219700.1100*
H2A0.384800.384500.458600.0620*
H3A0.188600.480700.400000.0720*
H4A0.197800.609500.469300.0760*
H5A0.286400.665200.401500.0720*
H6A0.484200.558400.453300.0620*
H8A0.332 (3)0.585 (3)0.5343 (13)0.0900*
H11A0.338500.189000.462300.0810*
H12A0.290500.015000.423300.0920*
H14A0.243200.167100.285100.0970*
H15A0.288500.341200.324300.0820*
H17A0.636200.670500.439600.0750*
H18A0.727800.787600.389700.0860*
H20A0.473900.756800.272200.0900*
H21A0.381300.641800.322400.0800*
H71A0.132800.317700.440200.1190*
H72A0.086000.427900.463000.1190*
H73A0.189800.364600.494300.1190*
H91A0.415400.798000.443200.1280*
H92A0.416600.734800.496100.1280*
H93A0.307600.796500.468900.1280*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0801 (5)0.0643 (5)0.1260 (7)0.0307 (4)0.0096 (5)0.0023 (5)
Cl20.0810 (6)0.1165 (8)0.1065 (7)0.0215 (5)0.0084 (5)0.0355 (6)
O10.0544 (10)0.0557 (10)0.0674 (11)0.0073 (8)0.0093 (8)0.0041 (9)
O80.0633 (11)0.0690 (12)0.0549 (10)0.0235 (9)0.0130 (9)0.0100 (9)
C20.0550 (14)0.0504 (14)0.0569 (14)0.0083 (11)0.0119 (11)0.0055 (11)
C30.0521 (14)0.0548 (15)0.0601 (15)0.0071 (11)0.0101 (11)0.0129 (12)
C40.0549 (14)0.0589 (15)0.0495 (13)0.0129 (12)0.0051 (11)0.0120 (12)
C50.0635 (15)0.0562 (15)0.0495 (13)0.0160 (12)0.0095 (11)0.0092 (12)
C60.0648 (16)0.0517 (14)0.0542 (14)0.0084 (12)0.0098 (12)0.0077 (12)
C70.0589 (17)0.0654 (18)0.099 (2)0.0033 (14)0.0148 (16)0.0051 (17)
C90.082 (2)0.0678 (18)0.0711 (18)0.0237 (16)0.0140 (15)0.0006 (15)
C100.0502 (13)0.0523 (14)0.0585 (14)0.0090 (11)0.0089 (11)0.0065 (12)
C110.0549 (14)0.0547 (15)0.0665 (16)0.0099 (12)0.0162 (12)0.0048 (13)
C120.0591 (16)0.0557 (15)0.0718 (17)0.0061 (13)0.0120 (13)0.0035 (13)
C130.0495 (14)0.0521 (15)0.0818 (19)0.0103 (12)0.0021 (13)0.0059 (14)
C140.0660 (17)0.0715 (19)0.084 (2)0.0208 (15)0.0261 (15)0.0102 (16)
C150.0708 (18)0.0689 (18)0.0702 (17)0.0169 (15)0.0234 (14)0.0004 (15)
C160.0641 (16)0.0532 (15)0.0579 (15)0.0035 (12)0.0066 (12)0.0019 (12)
C170.098 (2)0.0628 (19)0.087 (2)0.0037 (17)0.0236 (19)0.0137 (17)
C180.100 (3)0.0566 (18)0.106 (3)0.0126 (18)0.018 (2)0.0014 (18)
C190.0617 (17)0.078 (2)0.0700 (18)0.0044 (15)0.0029 (14)0.0165 (16)
C200.0662 (18)0.078 (2)0.077 (2)0.0013 (16)0.0150 (15)0.0009 (16)
C210.0718 (18)0.0594 (17)0.0770 (19)0.0017 (14)0.0167 (15)0.0112 (14)
Cl1A0.1483 (10)0.0920 (7)0.1186 (8)0.0418 (7)0.0546 (7)0.0428 (6)
Cl2A0.1416 (9)0.0872 (6)0.0903 (6)0.0260 (6)0.0513 (6)0.0007 (5)
O1A0.0570 (10)0.0522 (10)0.0480 (9)0.0117 (8)0.0123 (7)0.0012 (8)
O8A0.0983 (15)0.0662 (13)0.0471 (10)0.0292 (11)0.0149 (10)0.0000 (9)
C2A0.0515 (13)0.0585 (15)0.0445 (12)0.0122 (11)0.0076 (10)0.0052 (11)
C3A0.0521 (14)0.0737 (18)0.0557 (14)0.0218 (13)0.0106 (11)0.0101 (13)
C4A0.0661 (16)0.0662 (17)0.0611 (16)0.0332 (14)0.0196 (13)0.0103 (13)
C5A0.0677 (16)0.0573 (15)0.0562 (14)0.0282 (13)0.0147 (12)0.0079 (12)
C6A0.0588 (14)0.0508 (14)0.0449 (12)0.0161 (11)0.0053 (11)0.0010 (11)
C7A0.0643 (18)0.095 (2)0.083 (2)0.0153 (17)0.0231 (16)0.0096 (18)
C9A0.113 (3)0.0608 (18)0.091 (2)0.0255 (18)0.041 (2)0.0074 (17)
C10A0.0517 (14)0.0630 (16)0.0519 (14)0.0085 (12)0.0100 (11)0.0004 (12)
C11A0.0807 (19)0.0675 (18)0.0566 (15)0.0035 (15)0.0176 (14)0.0025 (14)
C12A0.093 (2)0.0638 (18)0.079 (2)0.0050 (16)0.0298 (17)0.0030 (16)
C13A0.076 (2)0.077 (2)0.076 (2)0.0107 (16)0.0274 (16)0.0162 (17)
C14A0.096 (2)0.088 (2)0.0563 (16)0.0019 (19)0.0096 (16)0.0124 (17)
C15A0.083 (2)0.0708 (19)0.0519 (15)0.0074 (15)0.0089 (14)0.0019 (14)
C16A0.0613 (15)0.0481 (13)0.0457 (12)0.0163 (11)0.0071 (11)0.0022 (11)
C17A0.0704 (17)0.0625 (16)0.0508 (14)0.0049 (14)0.0029 (13)0.0048 (13)
C18A0.078 (2)0.0689 (19)0.0671 (18)0.0087 (15)0.0116 (15)0.0139 (15)
C19A0.092 (2)0.0562 (16)0.0628 (17)0.0001 (15)0.0260 (16)0.0028 (13)
C20A0.088 (2)0.083 (2)0.0534 (15)0.0078 (18)0.0100 (15)0.0139 (15)
C21A0.0646 (17)0.079 (2)0.0541 (15)0.0040 (15)0.0013 (13)0.0092 (14)
Geometric parameters (Å, º) top
Cl1—C131.737 (3)C14—H140.9298
Cl2—C191.744 (3)C15—H150.9313
Cl1A—C13A1.745 (4)C17—H170.9303
Cl2A—C19A1.740 (3)C18—H180.9298
O1—C61.431 (3)C20—H200.9308
O1—C21.425 (3)C21—H210.9291
O8—C41.437 (3)C2A—C3A1.540 (3)
O8—H80.84 (4)C2A—C10A1.504 (3)
O1A—C2A1.447 (3)C3A—C7A1.520 (4)
O1A—C6A1.447 (3)C3A—C4A1.522 (3)
O8A—C4A1.431 (3)C4A—C5A1.520 (3)
O8A—H8A0.81 (3)C5A—C9A1.523 (4)
C2—C101.509 (3)C5A—C6A1.534 (3)
C2—C31.540 (4)C6A—C16A1.505 (3)
C3—C71.513 (4)C10A—C11A1.380 (4)
C3—C41.529 (3)C10A—C15A1.382 (4)
C4—C51.515 (3)C11A—C12A1.385 (5)
C5—C61.538 (4)C12A—C13A1.363 (5)
C5—C91.524 (4)C13A—C14A1.371 (5)
C6—C161.502 (3)C14A—C15A1.382 (5)
C10—C111.376 (4)C16A—C21A1.383 (4)
C10—C151.383 (4)C16A—C17A1.383 (3)
C11—C121.384 (3)C17A—C18A1.381 (4)
C12—C131.366 (4)C18A—C19A1.364 (4)
C13—C141.368 (4)C19A—C20A1.368 (5)
C14—C151.383 (5)C20A—C21A1.379 (4)
C16—C171.386 (4)C2A—H2A0.9794
C16—C211.377 (4)C3A—H3A0.9793
C17—C181.385 (5)C4A—H4A0.9796
C18—C191.357 (5)C5A—H5A0.9799
C19—C201.371 (5)C6A—H6A0.9799
C20—C211.378 (5)C7A—H71A0.9600
C2—H20.9806C7A—H72A0.9600
C3—H30.9790C7A—H73A0.9595
C4—H40.9798C9A—H91A0.9596
C5—H50.9799C9A—H92A0.9605
C6—H60.9793C9A—H93A0.9611
C7—H720.9613C11A—H11A0.9292
C7—H730.9597C12A—H12A0.9299
C7—H710.9609C14A—H14A0.9297
C9—H930.9598C15A—H15A0.9301
C9—H920.9603C17A—H17A0.9299
C9—H910.9608C18A—H18A0.9302
C11—H110.9310C20A—H20A0.9303
C12—H120.9308C21A—H21A0.9302
Cl1···C4Ai3.563 (3)H3···C153.0864
Cl1···C7Aii3.585 (4)H3···H52.4612
Cl1···H4Ai2.6102H3A···H5A2.4616
Cl2···H21iii2.9153H3A···C18i3.0994
Cl2···H21Aiii2.8808H3A···C19i3.0727
Cl2A···H15Aiv3.0803H4···H20A2.5116
O1A···O8v2.850 (3)H4···H712.5022
O8···O8Avi2.833 (3)H4···H932.5199
O8···O1Aiv2.850 (3)H4A···H72A2.5122
O8A···C6Avii3.380 (3)H4A···H93A2.5636
O8A···C17Avii3.377 (3)H4A···Cl1iii2.6102
O8A···O8viii2.833 (3)H5···C213.0288
O1···H212.5155H5···H32.4612
O1···H152.4561H5A···C21A2.8397
O1A···H15A2.5756H5A···H3A2.4616
O1A···H21A2.7364H5A···H21A2.5482
O1A···H8v2.04 (4)H6···O82.6167
O8···H922.6537H6···H22.4505
O8···H8Avi2.09 (3)H6···H172.4073
O8···H722.5984H6A···O8Avii2.5577
O8···H62.6167H6A···H2A2.3822
O8···H22.5864H6A···O8A2.6840
O8A···H2A2.4371H6A···H17A2.3398
O8A···H73A2.5782H6A···H92A2.5502
O8A···H92A2.6614H8···H922.5461
O8A···H17Avii2.6992H8···C92.98 (4)
O8A···H6A2.6840H8···C6Aiv2.84 (4)
O8A···H6Avii2.5577H8···O1Aiv2.04 (4)
C4A···Cl1iii3.563 (3)H8···C2Aiv2.76 (4)
C6A···O8Avii3.380 (3)H8···C10Aiv2.95 (4)
C7···C113.308 (4)H8···H8Avi2.40 (5)
C7A···Cl1ix3.585 (4)H8A···C9A2.81 (3)
C7A···C11A3.299 (5)H8A···O8viii2.09 (3)
C9···C173.394 (5)H8A···H8viii2.40 (5)
C9···C21Aiv3.586 (5)H8A···H92A2.3401
C9A···C17A3.473 (4)H11···H22.4212
C11···C73.308 (4)H11···H93Avi2.5779
C11···C13x3.481 (4)H11A···H2A2.3626
C11···C12x3.568 (4)H15···O12.4561
C11A···C7A3.299 (5)H15A···O1A2.5756
C12···C12x3.427 (4)H15A···Cl2Av3.0803
C12···C13x3.596 (4)H17···H62.4073
C12···C11x3.568 (4)H17A···O8Avii2.6992
C13···C12x3.596 (4)H17A···H6A2.3398
C13···C11x3.481 (4)H17A···H73Avii2.5267
C17···C93.394 (5)H18A···C12iv3.0911
C17A···O8Avii3.377 (3)H18A···C13iv3.0455
C17A···C9A3.473 (4)H20A···H42.5116
C21A···C9v3.586 (5)H21···O12.5155
C2A···H8v2.76 (4)H21···Cl2i2.9153
C5A···H21A3.0772H21A···O1A2.7364
C6A···H8v2.84 (4)H21A···Cl2i2.8808
C9···H82.98 (4)H21A···C5A3.0772
C9A···H8A2.81 (3)H21A···H5A2.5482
C10···H732.7253H71···H42.5022
C10A···H8v2.95 (4)H71A···C10A2.6691
C10A···H71A2.6691H71A···C11A2.7988
C11···H732.7641H72···O82.5984
C11A···H71A2.7988H72A···H4A2.5122
C12···H18Av3.0911H73···C102.7253
C13···H18Av3.0455H73···C112.7641
C15···H33.0864H73A···O8A2.5782
C16···H912.6970H73A···H17Avii2.5267
C16A···H92v2.7996H91···C162.6970
C16A···H91A2.6225H91···C172.8349
C17···H912.8349H91A···C16A2.6225
C17A···H92v2.8536H91A···C17A2.9136
C17A···H91A2.9136H92···O82.6537
C18···H3Aiii3.0994H92···H82.5461
C18A···H92v3.0629H92···C16Aiv2.7996
C19···H3Aiii3.0727H92···C17Aiv2.8536
C21···H53.0288H92···C18Aiv3.0629
C21A···H5A2.8397H92···C21Aiv2.9033
C21A···H92v2.9033H92A···H8A2.3401
H2···H62.4505H92A···O8A2.6614
H2···H112.4212H92A···H6A2.5502
H2···O82.5864H93···H42.5199
H2A···O8A2.4371H93A···H4A2.5636
H2A···H6A2.3822H93A···H11viii2.5779
H2A···H11A2.3626
C2—O1—C6114.78 (18)C20—C21—H21118.95
C4—O8—H8111 (2)C16—C21—H21119.00
C2A—O1A—C6A112.57 (17)O1A—C2A—C3A109.36 (19)
C4A—O8A—H8A113 (2)C3A—C2A—C10A113.1 (2)
C3—C2—C10112.3 (2)O1A—C2A—C10A109.24 (19)
O1—C2—C3110.8 (2)C2A—C3A—C4A107.4 (2)
O1—C2—C10106.90 (19)C4A—C3A—C7A112.3 (2)
C4—C3—C7112.2 (2)C2A—C3A—C7A114.5 (2)
C2—C3—C7113.9 (2)O8A—C4A—C5A111.9 (2)
C2—C3—C4108.56 (19)C3A—C4A—C5A111.0 (2)
C3—C4—C5110.9 (2)O8A—C4A—C3A106.67 (19)
O8—C4—C5110.80 (19)C4A—C5A—C6A109.85 (19)
O8—C4—C3107.79 (19)C6A—C5A—C9A111.1 (2)
C4—C5—C9112.0 (2)C4A—C5A—C9A112.6 (2)
C6—C5—C9112.9 (2)O1A—C6A—C5A111.15 (19)
C4—C5—C6109.3 (2)C5A—C6A—C16A111.54 (19)
O1—C6—C5110.07 (19)O1A—C6A—C16A108.33 (18)
C5—C6—C16113.1 (2)C2A—C10A—C11A120.0 (2)
O1—C6—C16106.96 (19)C2A—C10A—C15A122.2 (2)
C2—C10—C11121.1 (2)C11A—C10A—C15A117.7 (3)
C11—C10—C15118.1 (2)C10A—C11A—C12A121.8 (3)
C2—C10—C15120.8 (2)C11A—C12A—C13A119.0 (3)
C10—C11—C12121.9 (2)Cl1A—C13A—C14A120.0 (3)
C11—C12—C13118.4 (2)C12A—C13A—C14A120.7 (3)
C12—C13—C14121.4 (2)Cl1A—C13A—C12A119.3 (3)
Cl1—C13—C12119.2 (2)C13A—C14A—C15A119.8 (3)
Cl1—C13—C14119.4 (2)C10A—C15A—C14A121.0 (3)
C13—C14—C15119.4 (3)C6A—C16A—C21A121.2 (2)
C10—C15—C14120.7 (3)C17A—C16A—C21A117.6 (2)
C6—C16—C17121.5 (2)C6A—C16A—C17A121.1 (2)
C17—C16—C21117.3 (3)C16A—C17A—C18A121.3 (3)
C6—C16—C21121.2 (2)C17A—C18A—C19A119.6 (3)
C16—C17—C18121.2 (3)Cl2A—C19A—C18A119.8 (3)
C17—C18—C19119.6 (3)Cl2A—C19A—C20A119.6 (2)
Cl2—C19—C20119.1 (2)C18A—C19A—C20A120.6 (3)
Cl2—C19—C18120.0 (3)C19A—C20A—C21A119.5 (3)
C18—C19—C20120.9 (3)C16A—C21A—C20A121.4 (3)
C19—C20—C21118.9 (3)O1A—C2A—H2A108.32
C16—C21—C20122.1 (3)C3A—C2A—H2A108.46
O1—C2—H2108.87C10A—C2A—H2A108.29
C3—C2—H2108.96C2A—C3A—H3A107.48
C10—C2—H2108.93C4A—C3A—H3A107.45
C4—C3—H3107.36C7A—C3A—H3A107.39
C2—C3—H3107.28O8A—C4A—H4A109.03
C7—C3—H3107.29C3A—C4A—H4A109.09
C3—C4—H4109.07C5A—C4A—H4A109.03
C5—C4—H4109.03C4A—C5A—H5A107.66
O8—C4—H4109.18C6A—C5A—H5A107.67
C6—C5—H5107.47C9A—C5A—H5A107.74
C9—C5—H5107.39O1A—C6A—H6A108.61
C4—C5—H5107.46C5A—C6A—H6A108.57
C16—C6—H6108.83C16A—C6A—H6A108.57
O1—C6—H6108.85C3A—C7A—H71A109.44
C5—C6—H6108.94C3A—C7A—H72A109.52
C3—C7—H73109.52C3A—C7A—H73A109.47
C3—C7—H71109.44H71A—C7A—H72A109.48
H71—C7—H73109.51H71A—C7A—H73A109.41
H72—C7—H73109.44H72A—C7A—H73A109.51
H71—C7—H72109.49C5A—C9A—H91A109.48
C3—C7—H72109.44C5A—C9A—H92A109.49
C5—C9—H92109.45C5A—C9A—H93A109.46
H91—C9—H92109.50H91A—C9A—H92A109.49
H91—C9—H93109.39H91A—C9A—H93A109.51
C5—C9—H93109.48H92A—C9A—H93A109.39
H92—C9—H93109.55C10A—C11A—H11A119.17
C5—C9—H91109.45C12A—C11A—H11A119.06
C12—C11—H11119.05C11A—C12A—H12A120.49
C10—C11—H11119.05C13A—C12A—H12A120.48
C13—C12—H12120.83C13A—C14A—H14A120.09
C11—C12—H12120.77C15A—C14A—H14A120.14
C13—C14—H14120.28C10A—C15A—H15A119.56
C15—C14—H14120.31C14A—C15A—H15A119.47
C14—C15—H15119.55C16A—C17A—H17A119.32
C10—C15—H15119.70C18A—C17A—H17A119.38
C18—C17—H17119.38C17A—C18A—H18A120.13
C16—C17—H17119.43C19A—C18A—H18A120.27
C17—C18—H18120.21C19A—C20A—H20A120.30
C19—C18—H18120.18C21A—C20A—H20A120.17
C19—C20—H20120.62C16A—C21A—H21A119.34
C21—C20—H20120.45C20A—C21A—H21A119.31
C6—O1—C2—C359.0 (3)C17—C18—C19—Cl2178.9 (3)
C6—O1—C2—C10178.4 (2)Cl2—C19—C20—C21179.1 (2)
C2—O1—C6—C558.8 (3)C18—C19—C20—C210.5 (5)
C2—O1—C6—C16178.0 (2)C19—C20—C21—C160.4 (5)
C2A—O1A—C6A—C5A58.4 (2)O1A—C2A—C10A—C15A38.1 (3)
C6A—O1A—C2A—C3A62.5 (2)C10A—C2A—C3A—C7A51.7 (3)
C6A—O1A—C2A—C10A173.23 (19)O1A—C2A—C10A—C11A144.5 (3)
C2A—O1A—C6A—C16A178.74 (18)O1A—C2A—C3A—C4A60.9 (2)
O1—C2—C3—C455.2 (3)O1A—C2A—C3A—C7A173.6 (2)
O1—C2—C10—C11146.7 (2)C10A—C2A—C3A—C4A177.1 (2)
C10—C2—C3—C759.6 (3)C3A—C2A—C10A—C15A83.9 (3)
C10—C2—C3—C4174.7 (2)C3A—C2A—C10A—C11A93.5 (3)
C3—C2—C10—C1587.1 (3)C2A—C3A—C4A—O8A63.9 (2)
O1—C2—C10—C1534.6 (3)C7A—C3A—C4A—C5A175.0 (2)
C3—C2—C10—C1191.6 (3)C2A—C3A—C4A—C5A58.2 (3)
O1—C2—C3—C7179.0 (2)C7A—C3A—C4A—O8A62.8 (3)
C7—C3—C4—C5177.6 (2)O8A—C4A—C5A—C6A64.4 (3)
C2—C3—C4—C555.6 (3)C3A—C4A—C5A—C9A179.1 (2)
C2—C3—C4—O865.8 (2)O8A—C4A—C5A—C9A60.0 (3)
C7—C3—C4—O860.9 (3)C3A—C4A—C5A—C6A54.7 (3)
O8—C4—C5—C962.5 (3)C9A—C5A—C6A—O1A178.4 (2)
C3—C4—C5—C656.3 (3)C9A—C5A—C6A—C16A60.6 (3)
C3—C4—C5—C9177.8 (2)C4A—C5A—C6A—C16A174.2 (2)
O8—C4—C5—C663.4 (2)C4A—C5A—C6A—O1A53.2 (3)
C9—C5—C6—C1659.2 (3)O1A—C6A—C16A—C21A54.6 (3)
C4—C5—C6—C16175.36 (19)O1A—C6A—C16A—C17A128.8 (2)
C9—C5—C6—O1178.8 (2)C5A—C6A—C16A—C21A68.0 (3)
C4—C5—C6—O155.8 (3)C5A—C6A—C16A—C17A108.6 (3)
C5—C6—C16—C2180.7 (3)C2A—C10A—C11A—C12A175.1 (3)
O1—C6—C16—C17141.1 (3)C11A—C10A—C15A—C14A1.8 (5)
C5—C6—C16—C1797.5 (3)C15A—C10A—C11A—C12A2.4 (5)
O1—C6—C16—C2140.6 (3)C2A—C10A—C15A—C14A175.6 (3)
C2—C10—C11—C12177.6 (2)C10A—C11A—C12A—C13A1.2 (5)
C15—C10—C11—C121.1 (4)C11A—C12A—C13A—Cl1A180.0 (3)
C11—C10—C15—C140.9 (4)C11A—C12A—C13A—C14A0.6 (6)
C2—C10—C15—C14177.9 (3)Cl1A—C13A—C14A—C15A179.5 (3)
C10—C11—C12—C130.4 (4)C12A—C13A—C14A—C15A1.1 (6)
C11—C12—C13—Cl1179.2 (2)C13A—C14A—C15A—C10A0.1 (5)
C11—C12—C13—C140.7 (4)C21A—C16A—C17A—C18A1.6 (4)
Cl1—C13—C14—C15179.4 (2)C6A—C16A—C21A—C20A175.6 (3)
C12—C13—C14—C150.9 (4)C6A—C16A—C17A—C18A175.1 (3)
C13—C14—C15—C100.1 (4)C17A—C16A—C21A—C20A1.1 (4)
C21—C16—C17—C181.6 (5)C16A—C17A—C18A—C19A0.9 (4)
C6—C16—C17—C18176.7 (3)C17A—C18A—C19A—Cl2A179.3 (2)
C6—C16—C21—C20176.9 (3)C17A—C18A—C19A—C20A0.3 (5)
C17—C16—C21—C201.4 (4)C18A—C19A—C20A—C21A0.7 (5)
C16—C17—C18—C190.8 (5)Cl2A—C19A—C20A—C21A178.8 (3)
C17—C18—C19—C200.3 (5)C19A—C20A—C21A—C16A0.0 (5)
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x, y+1/2, z1/2; (iii) x, y+1/2, z+1/2; (iv) x+1, y+1/2, z+1/2; (v) x+1, y1/2, z+1/2; (vi) x, y+3/2, z1/2; (vii) x+1, y+1, z+1; (viii) x, y+3/2, z+1/2; (ix) x, y+1/2, z+1/2; (x) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O8—H8···O1Aiv0.84 (4)2.04 (4)2.850 (3)163 (3)
O8A—H8A···O8viii0.81 (3)2.09 (3)2.833 (3)152 (3)
C2A—H2A···O8A0.982.442.827 (3)103
C4A—H4A···Cl1iii0.982.613.563 (3)164
C6A—H6A···O8Avii0.982.563.380 (3)141
Symmetry codes: (iii) x, y+1/2, z+1/2; (iv) x+1, y+1/2, z+1/2; (vii) x+1, y+1, z+1; (viii) x, y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC19H20Cl2O2
Mr351.25
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)12.1315 (9), 11.7075 (19), 26.177 (3)
β (°) 99.728 (9)
V3)3664.4 (8)
Z8
Radiation typeMo Kα
µ (mm1)0.36
Crystal size (mm)0.2 × 0.2 × 0.1
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.650, 0.999
No. of measured, independent and
observed [I > 2σ(I)] reflections
7004, 6670, 5034
Rint0.027
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.146, 1.06
No. of reflections6670
No. of parameters423
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.50, 0.42

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, MolEN (Fair, 1990), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top
O1—C61.431 (3)O1A—C2A1.447 (3)
O1—C21.425 (3)O1A—C6A1.447 (3)
O8—C41.437 (3)O8A—C4A1.431 (3)
C2—O1—C6114.78 (18)O1—C6—C16106.96 (19)
C2A—O1A—C6A112.57 (17)O1A—C2A—C10A109.24 (19)
O1—C2—C10106.90 (19)O1A—C6A—C16A108.33 (18)
C2—O1—C6—C16178.0 (2)C9—C5—C6—O1178.8 (2)
C2A—O1A—C6A—C16A178.74 (18)C10A—C2A—C3A—C4A177.1 (2)
C10—C2—C3—C4174.7 (2)C7A—C3A—C4A—C5A175.0 (2)
C7—C3—C4—C5177.6 (2)C7A—C3A—C4A—O8A62.8 (3)
C7—C3—C4—O860.9 (3)O8A—C4A—C5A—C6A64.4 (3)
O8—C4—C5—C663.4 (2)C9A—C5A—C6A—O1A178.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O8—H8···O1Ai0.84 (4)2.04 (4)2.850 (3)163 (3)
O8A—H8A···O8ii0.81 (3)2.09 (3)2.833 (3)152 (3)
C4A—H4A···Cl1iii0.982.613.563 (3)164
C6A—H6A···O8Aiv0.982.563.380 (3)141
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x, y+3/2, z+1/2; (iii) x, y+1/2, z+1/2; (iv) x+1, y+1, z+1.
 

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