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The reaction of dimedone with 2,6-di­chloro­benz­aldehyde leads to the title compound, C23H26Cl2O4. In principle, the reaction could yield eight different stereoisomers. We have found four of them in the same crystal as two enantiomeric pairs of diastereomers, which means that the asymmetric unit is built up of two different diastereomers. Two of the three chiral centres display the same configuration, while the third is different in the two mol­ecules in the asymmetric unit. The packing of the mol­ecules is stabilized by hydrogen bonds between the hydroxy group and the carbonyl group attached to the cyclo­hexene ring, forming chains in which the different diastereomers alternate.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101000063/sk1447sup1.cif
Contains datablocks II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101000063/sk1447IIsup2.hkl
Contains datablock II

CCDC reference: 163920

Computing details top

Cell refinement: SMART (Siemens, 1995); data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991).

; top
Crystal data top
C23H26Cl2O4Z = 4
Mr = 437.34F(000) = 920
Triclinic, P1Dx = 1.332 Mg m3
a = 11.936 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.969 (4) ÅCell parameters from 6375 reflections
c = 16.204 (5) Åθ = 0–25°
α = 74.50 (1)°µ = 0.32 mm1
β = 90.16 (1)°T = 173 K
γ = 65.50 (1)°Block, colourless
V = 2180.9 (11) Å30.45 × 0.40 × 0.40 mm
Data collection top
Siemens CCD three-circle
diffractometer
9912 independent reflections
Radiation source: fine-focus sealed tube5279 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.079
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: empirical
SADABS (Sheldrick, 1996)
h = 1515
Tmin = 0.868, Tmax = 0.881k = 1616
27336 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.079Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.241H atoms treated by a mixture of independent and constrained refinement
S = 0.92 w = 1/[σ2(Fo2) + (0.1543P)2]
where P = (Fo2 + 2Fc2)/3
9912 reflections(Δ/σ)max = 0.001
525 parametersΔρmax = 0.84 e Å3
0 restraintsΔρmin = 0.81 e Å3
Special details top

Experimental. ;

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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
C10.4942 (4)0.3174 (3)0.7797 (2)0.0277 (9)
H10.48080.38090.80780.033*
C110.4188 (4)0.2546 (4)0.8236 (3)0.0304 (9)
C120.3335 (4)0.2406 (4)0.7800 (3)0.0302 (9)
O120.3118 (3)0.2712 (3)0.69313 (18)0.0326 (7)
C130.2492 (4)0.1880 (4)0.8212 (3)0.0380 (10)
H13C0.28600.10260.82560.046*
H13D0.16840.22690.78390.046*
C140.2275 (4)0.2027 (4)0.9113 (3)0.0378 (10)
C170.1642 (5)0.1252 (5)0.9563 (3)0.0537 (14)
H17D0.08310.15190.92340.080*
H17E0.15280.13191.01480.080*
H17F0.21620.04240.95930.080*
C180.1457 (5)0.3325 (5)0.9046 (4)0.0589 (15)
H18D0.18630.38170.87540.088*
H18E0.13330.34090.96270.088*
H18F0.06510.35830.87140.088*
C150.3535 (4)0.1624 (5)0.9613 (3)0.0424 (11)
H15C0.34050.18061.01700.051*
H15D0.39870.07520.97440.051*
C160.4337 (4)0.2168 (4)0.9164 (3)0.0343 (10)
O160.5134 (3)0.2267 (3)0.95794 (19)0.0442 (8)
C210.4349 (4)0.3842 (3)0.6848 (3)0.0271 (9)
H210.49990.40010.65220.033*
C220.3957 (4)0.3101 (3)0.6425 (3)0.0273 (9)
O220.5024 (2)0.2107 (2)0.64128 (19)0.0338 (7)
H220.48250.16050.63000.041*
C230.3227 (4)0.3780 (3)0.5535 (3)0.0282 (9)
H23C0.28780.32870.53600.034*
H23D0.38140.38800.51260.034*
C240.2152 (4)0.5017 (4)0.5433 (3)0.0317 (10)
C270.1046 (4)0.4933 (4)0.5866 (3)0.0451 (12)
H27D0.13100.45180.64840.068*
H27E0.07270.44930.56030.068*
H27F0.03910.57320.57900.068*
C280.1753 (4)0.5659 (4)0.4471 (3)0.0398 (11)
H28D0.24680.57090.41980.060*
H28E0.11000.64600.43920.060*
H28F0.14360.52210.42050.060*
C250.2648 (4)0.5711 (4)0.5839 (3)0.0378 (11)
H25C0.32550.58940.54870.045*
H25D0.19520.64720.58350.045*
C260.3257 (4)0.5035 (4)0.6747 (3)0.0328 (10)
O260.2924 (3)0.5399 (3)0.7358 (2)0.0480 (9)
C310.6331 (4)0.2494 (3)0.7869 (2)0.0277 (9)
C320.7058 (4)0.3126 (4)0.7741 (3)0.0314 (9)
Cl20.63358 (10)0.46609 (9)0.75792 (8)0.0422 (3)
C330.8314 (4)0.2639 (4)0.7732 (3)0.0389 (11)
H330.87440.31250.76280.047*
C340.8954 (4)0.1423 (4)0.7876 (3)0.0429 (11)
H340.98260.10660.78640.052*
C350.8303 (4)0.0745 (4)0.8037 (3)0.0381 (11)
H350.87320.00890.81460.046*
C360.7035 (4)0.1263 (4)0.8042 (3)0.0341 (10)
Cl60.63513 (11)0.02788 (9)0.82867 (8)0.0406 (3)
C1A0.3396 (4)0.8963 (3)0.6989 (2)0.0267 (9)
H1A0.29860.96910.71800.032*
C11A0.4774 (4)0.8648 (3)0.7046 (2)0.0257 (9)
C12A0.5592 (4)0.7733 (4)0.7702 (3)0.0272 (9)
O12A0.5274 (2)0.7055 (2)0.83566 (18)0.0318 (7)
C13A0.6947 (4)0.7390 (4)0.7814 (3)0.0315 (9)
H13A0.73880.65160.80530.038*
H13B0.71240.77370.82450.038*
C14A0.7474 (4)0.7773 (4)0.6994 (3)0.0310 (9)
C17A0.8761 (4)0.7653 (4)0.7239 (3)0.0417 (11)
H17A0.91060.79000.67140.063*
H17B0.93010.68240.75530.063*
H17C0.87060.81560.76070.063*
C18A0.7580 (4)0.6982 (4)0.6421 (3)0.0409 (11)
H18A0.67560.70450.62630.061*
H18B0.81320.61570.67350.061*
H18C0.79210.72370.58960.061*
C15A0.6587 (4)0.9071 (4)0.6500 (3)0.0324 (10)
H15A0.67780.95970.67610.039*
H15B0.67740.92320.58970.039*
C16A0.5222 (4)0.9409 (4)0.6480 (3)0.0298 (9)
O16A0.4482 (3)1.0390 (2)0.59961 (19)0.0363 (7)
C21A0.3180 (3)0.7969 (3)0.7630 (2)0.0256 (8)
H21A0.34580.72820.73880.031*
C22A0.3979 (4)0.7555 (4)0.8492 (3)0.0300 (9)
O22A0.3734 (3)0.8548 (2)0.87668 (18)0.0320 (7)
H22A0.41070.83340.92660.038*
C23A0.3829 (4)0.6553 (4)0.9144 (3)0.0328 (10)
H23A0.43380.63530.96970.039*
H23B0.41550.58440.89360.039*
C24A0.2488 (4)0.6839 (4)0.9312 (3)0.0338 (10)
C27A0.2441 (5)0.5682 (5)0.9845 (3)0.0523 (13)
H27A0.15880.58470.99610.078*
H27B0.29870.53621.03930.078*
H27C0.27190.51010.95200.078*
C28A0.1992 (4)0.7749 (5)0.9819 (3)0.0469 (12)
H28A0.11310.79030.99070.070*
H28B0.20230.84890.94920.070*
H28C0.25040.74351.03800.070*
C25A0.1652 (4)0.7321 (4)0.8448 (3)0.0327 (10)
H25A0.18110.66570.82040.039*
H25B0.07740.76360.85560.039*
C26A0.1841 (4)0.8280 (4)0.7793 (3)0.0292 (9)
O26A0.0997 (3)0.9216 (3)0.7402 (2)0.0428 (8)
C31A0.2781 (4)0.9254 (4)0.6079 (3)0.0287 (9)
C32A0.1761 (4)1.0334 (4)0.5675 (3)0.0321 (10)
Cl3A0.12852 (11)1.14906 (10)0.61450 (8)0.0473 (3)
C33A0.1093 (4)1.0563 (4)0.4905 (3)0.0389 (11)
H33A0.03861.12980.46730.047*
C34A0.1455 (4)0.9715 (4)0.4463 (3)0.0394 (11)
H34A0.09830.98560.39380.047*
C35A0.2503 (4)0.8670 (4)0.4796 (3)0.0362 (10)
H35A0.27910.81020.44860.043*
C36A0.3132 (4)0.8454 (3)0.5583 (3)0.0270 (9)
Cl6A0.44433 (9)0.71079 (9)0.59683 (7)0.0333 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.040 (2)0.023 (2)0.025 (2)0.0160 (18)0.0064 (18)0.0102 (17)
C110.036 (2)0.029 (2)0.032 (2)0.0148 (18)0.0110 (18)0.0159 (19)
C120.037 (2)0.027 (2)0.032 (2)0.0159 (18)0.0103 (18)0.0144 (18)
O120.0428 (17)0.0320 (16)0.0299 (16)0.0214 (14)0.0054 (13)0.0114 (13)
C130.048 (3)0.041 (3)0.037 (3)0.028 (2)0.009 (2)0.016 (2)
C140.039 (2)0.046 (3)0.035 (3)0.021 (2)0.013 (2)0.019 (2)
C170.052 (3)0.076 (4)0.041 (3)0.039 (3)0.013 (2)0.013 (3)
C180.049 (3)0.061 (4)0.075 (4)0.023 (3)0.022 (3)0.036 (3)
C150.049 (3)0.052 (3)0.031 (3)0.027 (2)0.011 (2)0.011 (2)
C160.034 (2)0.039 (3)0.032 (2)0.016 (2)0.0043 (19)0.013 (2)
O160.052 (2)0.059 (2)0.0290 (17)0.0311 (18)0.0027 (15)0.0143 (16)
C210.033 (2)0.022 (2)0.032 (2)0.0145 (17)0.0085 (17)0.0130 (18)
C220.030 (2)0.025 (2)0.031 (2)0.0123 (17)0.0084 (17)0.0128 (18)
O220.0394 (16)0.0199 (15)0.0400 (18)0.0064 (13)0.0030 (13)0.0162 (13)
C230.034 (2)0.025 (2)0.029 (2)0.0126 (18)0.0066 (17)0.0118 (18)
C240.033 (2)0.023 (2)0.040 (3)0.0090 (18)0.0017 (19)0.0140 (19)
C270.034 (2)0.050 (3)0.049 (3)0.012 (2)0.003 (2)0.020 (2)
C280.040 (3)0.031 (2)0.043 (3)0.008 (2)0.000 (2)0.013 (2)
C250.039 (2)0.026 (2)0.047 (3)0.0091 (19)0.001 (2)0.016 (2)
C260.034 (2)0.026 (2)0.043 (3)0.0129 (18)0.0043 (19)0.019 (2)
O260.052 (2)0.0377 (19)0.054 (2)0.0080 (15)0.0041 (16)0.0307 (17)
C310.033 (2)0.026 (2)0.025 (2)0.0115 (17)0.0041 (17)0.0109 (17)
C320.040 (2)0.029 (2)0.031 (2)0.0175 (19)0.0063 (19)0.0144 (19)
Cl20.0454 (7)0.0272 (6)0.0587 (8)0.0191 (5)0.0044 (5)0.0142 (5)
C330.046 (3)0.037 (3)0.036 (3)0.020 (2)0.008 (2)0.011 (2)
C340.034 (2)0.044 (3)0.046 (3)0.010 (2)0.007 (2)0.018 (2)
C350.041 (3)0.028 (2)0.041 (3)0.009 (2)0.001 (2)0.013 (2)
C360.050 (3)0.026 (2)0.030 (2)0.018 (2)0.003 (2)0.0112 (18)
Cl60.0541 (7)0.0259 (6)0.0451 (7)0.0190 (5)0.0074 (5)0.0124 (5)
C1A0.036 (2)0.020 (2)0.024 (2)0.0090 (17)0.0041 (17)0.0103 (17)
C11A0.033 (2)0.021 (2)0.027 (2)0.0110 (17)0.0073 (17)0.0137 (17)
C12A0.031 (2)0.027 (2)0.031 (2)0.0149 (18)0.0096 (18)0.0170 (18)
O12A0.0305 (15)0.0248 (15)0.0379 (17)0.0103 (12)0.0059 (13)0.0083 (13)
C13A0.033 (2)0.025 (2)0.034 (2)0.0100 (18)0.0004 (18)0.0100 (19)
C14A0.032 (2)0.028 (2)0.036 (2)0.0141 (18)0.0078 (18)0.0144 (19)
C17A0.039 (3)0.038 (3)0.047 (3)0.017 (2)0.005 (2)0.012 (2)
C18A0.039 (2)0.046 (3)0.049 (3)0.019 (2)0.012 (2)0.030 (2)
C15A0.038 (2)0.029 (2)0.038 (2)0.0190 (19)0.0067 (19)0.0127 (19)
C16A0.043 (2)0.024 (2)0.027 (2)0.0167 (19)0.0012 (18)0.0111 (18)
O16A0.0408 (17)0.0244 (16)0.0419 (18)0.0133 (14)0.0025 (14)0.0086 (14)
C21A0.031 (2)0.0201 (19)0.027 (2)0.0100 (17)0.0022 (17)0.0098 (17)
C22A0.031 (2)0.027 (2)0.036 (2)0.0121 (18)0.0099 (18)0.0162 (19)
O22A0.0412 (17)0.0285 (16)0.0297 (16)0.0141 (13)0.0032 (13)0.0155 (13)
C23A0.036 (2)0.026 (2)0.033 (2)0.0124 (18)0.0047 (19)0.0057 (19)
C24A0.038 (2)0.036 (2)0.032 (2)0.019 (2)0.0061 (19)0.013 (2)
C27A0.052 (3)0.055 (3)0.052 (3)0.033 (3)0.013 (2)0.003 (3)
C28A0.049 (3)0.065 (3)0.042 (3)0.032 (3)0.015 (2)0.030 (3)
C25A0.036 (2)0.037 (2)0.032 (2)0.019 (2)0.0111 (18)0.015 (2)
C26A0.030 (2)0.031 (2)0.030 (2)0.0127 (19)0.0045 (18)0.0161 (19)
O26A0.0307 (17)0.0360 (19)0.049 (2)0.0043 (14)0.0091 (14)0.0090 (16)
C31A0.031 (2)0.028 (2)0.029 (2)0.0154 (18)0.0050 (17)0.0081 (18)
C32A0.028 (2)0.028 (2)0.037 (3)0.0108 (18)0.0067 (19)0.0078 (19)
Cl3A0.0489 (7)0.0276 (6)0.0539 (8)0.0037 (5)0.0053 (6)0.0153 (5)
C33A0.030 (2)0.040 (3)0.041 (3)0.014 (2)0.003 (2)0.005 (2)
C34A0.041 (3)0.050 (3)0.029 (2)0.027 (2)0.001 (2)0.003 (2)
C35A0.044 (3)0.045 (3)0.032 (2)0.028 (2)0.012 (2)0.017 (2)
C36A0.030 (2)0.024 (2)0.032 (2)0.0145 (17)0.0034 (17)0.0097 (18)
Cl6A0.0358 (6)0.0302 (5)0.0390 (6)0.0129 (4)0.0081 (4)0.0201 (5)
Geometric parameters (Å, º) top
C1—C311.508 (5)C1A—C11A1.517 (5)
C1—C111.510 (6)C1A—C31A1.523 (5)
C1—C211.546 (6)C1A—C21A1.539 (5)
C1—H11.0000C1A—H1A1.0000
C11—C121.337 (6)C11A—C12A1.360 (6)
C11—C161.437 (6)C11A—C16A1.435 (6)
C12—O121.349 (5)C12A—O12A1.350 (5)
C12—C131.501 (6)C12A—C13A1.485 (6)
O12—C221.460 (5)O12A—C22A1.451 (5)
C13—C141.532 (6)C13A—C14A1.523 (6)
C13—H13C0.9900C13A—H13A0.9900
C13—H13D0.9900C13A—H13B0.9900
C14—C151.519 (6)C14A—C17A1.518 (6)
C14—C181.529 (7)C14A—C18A1.528 (6)
C14—C171.533 (7)C14A—C15A1.547 (6)
C17—H17D0.9800C17A—H17A0.9800
C17—H17E0.9800C17A—H17B0.9800
C17—H17F0.9800C17A—H17C0.9800
C18—H18D0.9800C18A—H18A0.9800
C18—H18E0.9800C18A—H18B0.9800
C18—H18F0.9800C18A—H18C0.9800
C15—C161.494 (6)C15A—C16A1.499 (6)
C15—H15C0.9900C15A—H15A0.9900
C15—H15D0.9900C15A—H15B0.9900
C16—O161.232 (5)C16A—O16A1.242 (5)
C21—C261.520 (5)C21A—C22A1.522 (6)
C21—C221.528 (5)C21A—C26A1.521 (5)
C21—H211.0000C21A—H21A1.0000
C22—O221.392 (4)C22A—O22A1.393 (5)
C22—C231.514 (6)C22A—C23A1.516 (6)
O22—H220.8400O22A—H22A0.8400
C23—C241.548 (5)C23A—C24A1.529 (6)
C23—H23C0.9900C23A—H23A0.9900
C23—H23D0.9900C23A—H23B0.9900
C24—C281.524 (6)C24A—C25A1.534 (6)
C24—C271.527 (6)C24A—C28A1.536 (6)
C24—C251.534 (6)C24A—C27A1.542 (6)
C27—H27D0.9800C27A—H27A0.9800
C27—H27E0.9800C27A—H27B0.9800
C27—H27F0.9800C27A—H27C0.9800
C28—H28D0.9800C28A—H28A0.9800
C28—H28E0.9800C28A—H28B0.9800
C28—H28F0.9800C28A—H28C0.9800
C25—C261.496 (6)C25A—C26A1.500 (6)
C25—H25C0.9900C25A—H25A0.9900
C25—H25D0.9900C25A—H25B0.9900
C26—O261.207 (5)C26A—O26A1.209 (5)
C31—C321.402 (6)C31A—C32A1.402 (6)
C31—C361.408 (6)C31A—C36A1.409 (5)
C32—C331.366 (6)C32A—C33A1.371 (6)
C32—Cl21.752 (4)C32A—Cl3A1.750 (4)
C33—C341.388 (6)C33A—C34A1.391 (6)
C33—H330.9500C33A—H33A0.9500
C34—C351.374 (7)C34A—C35A1.376 (6)
C34—H340.9500C34A—H34A0.9500
C35—C361.379 (6)C35A—C36A1.377 (6)
C35—H350.9500C35A—H35A0.9500
C36—Cl61.746 (4)C36A—Cl6A1.742 (4)
C31—C1—C11119.4 (3)C11A—C1A—C31A114.0 (3)
C31—C1—C21111.8 (3)C11A—C1A—C21A109.7 (3)
C11—C1—C21108.7 (3)C31A—C1A—C21A111.6 (3)
C31—C1—H1105.2C11A—C1A—H1A107.1
C11—C1—H1105.2C31A—C1A—H1A107.1
C21—C1—H1105.2C21A—C1A—H1A107.1
C12—C11—C16119.2 (4)C12A—C11A—C16A117.9 (4)
C12—C11—C1122.8 (4)C12A—C11A—C1A121.1 (3)
C16—C11—C1117.9 (4)C16A—C11A—C1A120.4 (3)
C11—C12—O12124.7 (4)O12A—C12A—C11A124.6 (3)
C11—C12—C13124.5 (4)O12A—C12A—C13A111.1 (3)
O12—C12—C13110.8 (3)C11A—C12A—C13A124.2 (4)
C12—O12—C22118.3 (3)C12A—O12A—C22A115.7 (3)
C12—C13—C14112.3 (4)C12A—C13A—C14A115.1 (3)
C12—C13—H13C109.1C12A—C13A—H13A108.5
C14—C13—H13C109.1C14A—C13A—H13A108.5
C12—C13—H13D109.1C12A—C13A—H13B108.5
C14—C13—H13D109.1C14A—C13A—H13B108.5
H13C—C13—H13D107.9H13A—C13A—H13B107.5
C15—C14—C18110.0 (4)C17A—C14A—C13A109.0 (4)
C15—C14—C13107.5 (4)C17A—C14A—C18A108.7 (3)
C18—C14—C13110.3 (4)C13A—C14A—C18A110.3 (4)
C15—C14—C17110.2 (4)C17A—C14A—C15A111.2 (3)
C18—C14—C17109.8 (4)C13A—C14A—C15A108.5 (3)
C13—C14—C17109.0 (4)C18A—C14A—C15A109.3 (4)
C14—C17—H17D109.5C14A—C17A—H17A109.5
C14—C17—H17E109.5C14A—C17A—H17B109.5
H17D—C17—H17E109.5H17A—C17A—H17B109.5
C14—C17—H17F109.5C14A—C17A—H17C109.5
H17D—C17—H17F109.5H17A—C17A—H17C109.5
H17E—C17—H17F109.5H17B—C17A—H17C109.5
C14—C18—H18D109.5C14A—C18A—H18A109.5
C14—C18—H18E109.5C14A—C18A—H18B109.5
H18D—C18—H18E109.5H18A—C18A—H18B109.5
C14—C18—H18F109.5C14A—C18A—H18C109.5
H18D—C18—H18F109.5H18A—C18A—H18C109.5
H18E—C18—H18F109.5H18B—C18A—H18C109.5
C16—C15—C14115.3 (4)C16A—C15A—C14A116.9 (3)
C16—C15—H15C108.4C16A—C15A—H15A108.1
C14—C15—H15C108.4C14A—C15A—H15A108.1
C16—C15—H15D108.4C16A—C15A—H15B108.1
C14—C15—H15D108.4C14A—C15A—H15B108.1
H15C—C15—H15D107.5H15A—C15A—H15B107.3
O16—C16—C11120.3 (4)O16A—C16A—C11A120.4 (4)
O16—C16—C15120.8 (4)O16A—C16A—C15A118.8 (4)
C11—C16—C15118.9 (4)C11A—C16A—C15A120.7 (4)
C26—C21—C22109.9 (3)C22A—C21A—C26A108.6 (3)
C26—C21—C1112.8 (3)C22A—C21A—C1A110.3 (3)
C22—C21—C1112.4 (3)C26A—C21A—C1A115.4 (3)
C26—C21—H21107.1C22A—C21A—H21A107.4
C22—C21—H21107.1C26A—C21A—H21A107.4
C1—C21—H21107.1C1A—C21A—H21A107.4
O22—C22—O12108.8 (3)O22A—C22A—O12A108.3 (3)
O22—C22—C23112.0 (3)O22A—C22A—C23A114.6 (3)
O12—C22—C23104.5 (3)O12A—C22A—C23A104.8 (3)
O22—C22—C21107.6 (3)O22A—C22A—C21A107.7 (3)
O12—C22—C21110.1 (3)O12A—C22A—C21A108.5 (3)
C23—C22—C21113.7 (3)C23A—C22A—C21A112.7 (3)
C22—O22—H22109.5C22A—O22A—H22A109.5
C22—C23—C24116.9 (3)C22A—C23A—C24A114.0 (3)
C22—C23—H23C108.1C22A—C23A—H23A108.7
C24—C23—H23C108.1C24A—C23A—H23A108.7
C22—C23—H23D108.1C22A—C23A—H23B108.7
C24—C23—H23D108.1C24A—C23A—H23B108.7
H23C—C23—H23D107.3H23A—C23A—H23B107.6
C28—C24—C27110.0 (4)C23A—C24A—C25A109.4 (3)
C28—C24—C25108.9 (4)C23A—C24A—C28A112.7 (4)
C27—C24—C25109.6 (4)C25A—C24A—C28A109.0 (4)
C28—C24—C23108.2 (3)C23A—C24A—C27A108.2 (4)
C27—C24—C23112.1 (4)C25A—C24A—C27A109.2 (4)
C25—C24—C23108.0 (3)C28A—C24A—C27A108.3 (4)
C24—C27—H27D109.5C24A—C27A—H27A109.5
C24—C27—H27E109.5C24A—C27A—H27B109.5
H27D—C27—H27E109.5H27A—C27A—H27B109.5
C24—C27—H27F109.5C24A—C27A—H27C109.5
H27D—C27—H27F109.5H27A—C27A—H27C109.5
H27E—C27—H27F109.5H27B—C27A—H27C109.5
C24—C28—H28D109.5C24A—C28A—H28A109.5
C24—C28—H28E109.5C24A—C28A—H28B109.5
H28D—C28—H28E109.5H28A—C28A—H28B109.5
C24—C28—H28F109.5C24A—C28A—H28C109.5
H28D—C28—H28F109.5H28A—C28A—H28C109.5
H28E—C28—H28F109.5H28B—C28A—H28C109.5
C26—C25—C24112.0 (4)C26A—C25A—C24A114.0 (3)
C26—C25—H25C109.2C26A—C25A—H25A108.7
C24—C25—H25C109.2C24A—C25A—H25A108.7
C26—C25—H25D109.2C26A—C25A—H25B108.7
C24—C25—H25D109.2C24A—C25A—H25B108.7
H25C—C25—H25D107.9H25A—C25A—H25B107.6
O26—C26—C25123.3 (4)O26A—C26A—C25A123.1 (4)
O26—C26—C21121.9 (4)O26A—C26A—C21A122.0 (4)
C25—C26—C21114.8 (4)C25A—C26A—C21A114.8 (3)
C32—C31—C36113.2 (4)C32A—C31A—C36A113.6 (4)
C32—C31—C1118.6 (4)C32A—C31A—C1A122.5 (4)
C36—C31—C1128.2 (4)C36A—C31A—C1A123.8 (4)
C33—C32—C31125.1 (4)C33A—C32A—C31A123.7 (4)
C33—C32—Cl2115.9 (3)C33A—C32A—Cl3A116.2 (3)
C31—C32—Cl2119.0 (3)C31A—C32A—Cl3A120.1 (3)
C32—C33—C34119.1 (4)C32A—C33A—C34A119.8 (4)
C32—C33—H33120.4C32A—C33A—H33A120.1
C34—C33—H33120.4C34A—C33A—H33A120.1
C35—C34—C33118.8 (4)C35A—C34A—C33A119.2 (4)
C35—C34—H34120.6C35A—C34A—H34A120.4
C33—C34—H34120.6C33A—C34A—H34A120.4
C34—C35—C36120.8 (4)C34A—C35A—C36A119.5 (4)
C34—C35—H35119.6C34A—C35A—H35A120.3
C36—C35—H35119.6C36A—C35A—H35A120.3
C35—C36—C31123.0 (4)C35A—C36A—C31A124.0 (4)
C35—C36—Cl6115.2 (3)C35A—C36A—Cl6A116.9 (3)
C31—C36—Cl6121.8 (3)C31A—C36A—Cl6A119.1 (3)
C31—C1—C11—C12116.6 (4)C31A—C1A—C11A—C12A137.8 (4)
C21—C1—C11—C1213.2 (5)C21A—C1A—C11A—C12A11.8 (5)
C31—C1—C11—C1668.1 (5)C31A—C1A—C11A—C16A51.0 (5)
C21—C1—C11—C16162.0 (3)C21A—C1A—C11A—C16A176.9 (3)
C16—C11—C12—O12179.2 (4)C16A—C11A—C12A—O12A169.7 (3)
C1—C11—C12—O125.6 (6)C1A—C11A—C12A—O12A1.8 (6)
C16—C11—C12—C130.6 (6)C16A—C11A—C12A—C13A6.9 (6)
C1—C11—C12—C13174.6 (4)C1A—C11A—C12A—C13A178.4 (3)
C11—C12—O12—C227.3 (6)C11A—C12A—O12A—C22A18.3 (5)
C13—C12—O12—C22172.5 (3)C13A—C12A—O12A—C22A158.7 (3)
C11—C12—C13—C1425.6 (6)O12A—C12A—C13A—C14A159.7 (3)
O12—C12—C13—C14154.6 (4)C11A—C12A—C13A—C14A23.3 (6)
C12—C13—C14—C1548.7 (5)C12A—C13A—C14A—C17A165.5 (3)
C12—C13—C14—C1871.1 (5)C12A—C13A—C14A—C18A75.3 (4)
C12—C13—C14—C17168.2 (4)C12A—C13A—C14A—C15A44.3 (5)
C18—C14—C15—C1668.8 (5)C17A—C14A—C15A—C16A159.9 (4)
C13—C14—C15—C1651.2 (5)C13A—C14A—C15A—C16A40.1 (5)
C17—C14—C15—C16169.9 (4)C18A—C14A—C15A—C16A80.2 (4)
C12—C11—C16—O16178.5 (4)C12A—C11A—C16A—O16A164.4 (4)
C1—C11—C16—O166.1 (6)C1A—C11A—C16A—O16A7.2 (5)
C12—C11—C16—C150.2 (6)C12A—C11A—C16A—C15A11.8 (5)
C1—C11—C16—C15175.6 (4)C1A—C11A—C16A—C15A176.6 (3)
C14—C15—C16—O16153.6 (4)C14A—C15A—C16A—O16A170.3 (4)
C14—C15—C16—C1128.1 (6)C14A—C15A—C16A—C11A13.4 (5)
C31—C1—C21—C26144.0 (3)C11A—C1A—C21A—C22A43.1 (4)
C11—C1—C21—C2682.1 (4)C31A—C1A—C21A—C22A170.4 (3)
C31—C1—C21—C2291.1 (4)C11A—C1A—C21A—C26A166.6 (3)
C11—C1—C21—C2242.8 (4)C31A—C1A—C21A—C26A66.1 (4)
C12—O12—C22—O2280.2 (4)C12A—O12A—C22A—O22A66.6 (4)
C12—O12—C22—C23160.0 (3)C12A—O12A—C22A—C23A170.6 (3)
C12—O12—C22—C2137.4 (4)C12A—O12A—C22A—C21A50.0 (4)
C26—C21—C22—O22170.7 (3)C26A—C21A—C22A—O22A73.3 (4)
C1—C21—C22—O2262.8 (4)C1A—C21A—C22A—O22A54.0 (4)
C26—C21—C22—O1270.8 (4)C26A—C21A—C22A—O12A169.7 (3)
C1—C21—C22—O1255.7 (4)C1A—C21A—C22A—O12A63.0 (4)
C26—C21—C22—C2346.1 (4)C26A—C21A—C22A—C23A54.0 (4)
C1—C21—C22—C23172.6 (3)C1A—C21A—C22A—C23A178.6 (3)
O22—C22—C23—C24169.5 (3)O22A—C22A—C23A—C24A67.9 (5)
O12—C22—C23—C2472.9 (4)O12A—C22A—C23A—C24A173.5 (3)
C21—C22—C23—C2447.3 (5)C21A—C22A—C23A—C24A55.7 (5)
C22—C23—C24—C28166.6 (3)C22A—C23A—C24A—C25A50.5 (5)
C22—C23—C24—C2772.0 (5)C22A—C23A—C24A—C28A70.9 (5)
C22—C23—C24—C2548.9 (5)C22A—C23A—C24A—C27A169.4 (4)
C28—C24—C25—C26170.2 (3)C23A—C24A—C25A—C26A48.5 (5)
C27—C24—C25—C2669.5 (5)C28A—C24A—C25A—C26A75.1 (4)
C23—C24—C25—C2653.0 (5)C27A—C24A—C25A—C26A166.7 (4)
C24—C25—C26—O26121.5 (5)C24A—C25A—C26A—O26A129.9 (4)
C24—C25—C26—C2159.0 (5)C24A—C25A—C26A—C21A52.4 (5)
C22—C21—C26—O26127.1 (4)C22A—C21A—C26A—O26A129.2 (4)
C1—C21—C26—O260.8 (6)C1A—C21A—C26A—O26A4.7 (5)
C22—C21—C26—C2553.4 (5)C22A—C21A—C26A—C25A53.1 (4)
C1—C21—C26—C25179.7 (3)C1A—C21A—C26A—C25A177.5 (3)
C11—C1—C31—C32157.6 (4)C11A—C1A—C31A—C32A123.4 (4)
C21—C1—C31—C3273.9 (4)C21A—C1A—C31A—C32A111.7 (4)
C11—C1—C31—C3623.5 (6)C11A—C1A—C31A—C36A60.1 (5)
C21—C1—C31—C36105.0 (5)C21A—C1A—C31A—C36A64.8 (5)
C36—C31—C32—C333.4 (6)C36A—C31A—C32A—C33A5.3 (6)
C1—C31—C32—C33175.6 (4)C1A—C31A—C32A—C33A171.5 (4)
C36—C31—C32—Cl2176.5 (3)C36A—C31A—C32A—Cl3A173.8 (3)
C1—C31—C32—Cl24.5 (5)C1A—C31A—C32A—Cl3A9.4 (5)
C31—C32—C33—C341.4 (7)C31A—C32A—C33A—C34A2.9 (7)
Cl2—C32—C33—C34178.5 (3)Cl3A—C32A—C33A—C34A176.3 (3)
C32—C33—C34—C351.0 (7)C32A—C33A—C34A—C35A1.9 (7)
C33—C34—C35—C361.0 (7)C33A—C34A—C35A—C36A3.8 (6)
C34—C35—C36—C311.3 (7)C34A—C35A—C36A—C31A1.0 (6)
C34—C35—C36—Cl6178.2 (4)C34A—C35A—C36A—Cl6A179.5 (3)
C32—C31—C36—C353.3 (6)C32A—C31A—C36A—C35A3.3 (6)
C1—C31—C36—C35175.6 (4)C1A—C31A—C36A—C35A173.4 (4)
C32—C31—C36—Cl6176.2 (3)C32A—C31A—C36A—Cl6A176.1 (3)
C1—C31—C36—Cl64.9 (6)C1A—C31A—C36A—Cl6A7.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O22A—H22A···O16i0.841.882.721 (4)174
O22—H22···O16Aii0.841.962.799 (4)176
Symmetry codes: (i) x+1, y+1, z+2; (ii) x, y1, z.
 

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