Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101000063/sk1447sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101000063/sk1447IIsup2.hkl |
CCDC reference: 163920
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).
C23H26Cl2O4 | Z = 4 |
Mr = 437.34 | F(000) = 920 |
Triclinic, P1 | Dx = 1.332 Mg m−3 |
a = 11.936 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.969 (4) Å | Cell parameters from 6375 reflections |
c = 16.204 (5) Å | θ = 0–25° |
α = 74.50 (1)° | µ = 0.32 mm−1 |
β = 90.16 (1)° | T = 173 K |
γ = 65.50 (1)° | Block, colourless |
V = 2180.9 (11) Å3 | 0.45 × 0.40 × 0.40 mm |
Siemens CCD three-circle diffractometer | 9912 independent reflections |
Radiation source: fine-focus sealed tube | 5279 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.079 |
ω scans | θmax = 27.5°, θmin = 1.8° |
Absorption correction: empirical SADABS (Sheldrick, 1996) | h = −15→15 |
Tmin = 0.868, Tmax = 0.881 | k = −16→16 |
27336 measured reflections | l = −21→21 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.079 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.241 | H 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 parameters | Δρmax = 0.84 e Å−3 |
0 restraints | Δρmin = −0.81 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.4942 (4) | 0.3174 (3) | 0.7797 (2) | 0.0277 (9) | |
H1 | 0.4808 | 0.3809 | 0.8078 | 0.033* | |
C11 | 0.4188 (4) | 0.2546 (4) | 0.8236 (3) | 0.0304 (9) | |
C12 | 0.3335 (4) | 0.2406 (4) | 0.7800 (3) | 0.0302 (9) | |
O12 | 0.3118 (3) | 0.2712 (3) | 0.69313 (18) | 0.0326 (7) | |
C13 | 0.2492 (4) | 0.1880 (4) | 0.8212 (3) | 0.0380 (10) | |
H13C | 0.2860 | 0.1026 | 0.8256 | 0.046* | |
H13D | 0.1684 | 0.2269 | 0.7839 | 0.046* | |
C14 | 0.2275 (4) | 0.2027 (4) | 0.9113 (3) | 0.0378 (10) | |
C17 | 0.1642 (5) | 0.1252 (5) | 0.9563 (3) | 0.0537 (14) | |
H17D | 0.0831 | 0.1519 | 0.9234 | 0.080* | |
H17E | 0.1528 | 0.1319 | 1.0148 | 0.080* | |
H17F | 0.2162 | 0.0424 | 0.9593 | 0.080* | |
C18 | 0.1457 (5) | 0.3325 (5) | 0.9046 (4) | 0.0589 (15) | |
H18D | 0.1863 | 0.3817 | 0.8754 | 0.088* | |
H18E | 0.1333 | 0.3409 | 0.9627 | 0.088* | |
H18F | 0.0651 | 0.3583 | 0.8714 | 0.088* | |
C15 | 0.3535 (4) | 0.1624 (5) | 0.9613 (3) | 0.0424 (11) | |
H15C | 0.3405 | 0.1806 | 1.0170 | 0.051* | |
H15D | 0.3987 | 0.0752 | 0.9744 | 0.051* | |
C16 | 0.4337 (4) | 0.2168 (4) | 0.9164 (3) | 0.0343 (10) | |
O16 | 0.5134 (3) | 0.2267 (3) | 0.95794 (19) | 0.0442 (8) | |
C21 | 0.4349 (4) | 0.3842 (3) | 0.6848 (3) | 0.0271 (9) | |
H21 | 0.4999 | 0.4001 | 0.6522 | 0.033* | |
C22 | 0.3957 (4) | 0.3101 (3) | 0.6425 (3) | 0.0273 (9) | |
O22 | 0.5024 (2) | 0.2107 (2) | 0.64128 (19) | 0.0338 (7) | |
H22 | 0.4825 | 0.1605 | 0.6300 | 0.041* | |
C23 | 0.3227 (4) | 0.3780 (3) | 0.5535 (3) | 0.0282 (9) | |
H23C | 0.2878 | 0.3287 | 0.5360 | 0.034* | |
H23D | 0.3814 | 0.3880 | 0.5126 | 0.034* | |
C24 | 0.2152 (4) | 0.5017 (4) | 0.5433 (3) | 0.0317 (10) | |
C27 | 0.1046 (4) | 0.4933 (4) | 0.5866 (3) | 0.0451 (12) | |
H27D | 0.1310 | 0.4518 | 0.6484 | 0.068* | |
H27E | 0.0727 | 0.4493 | 0.5603 | 0.068* | |
H27F | 0.0391 | 0.5732 | 0.5790 | 0.068* | |
C28 | 0.1753 (4) | 0.5659 (4) | 0.4471 (3) | 0.0398 (11) | |
H28D | 0.2468 | 0.5709 | 0.4198 | 0.060* | |
H28E | 0.1100 | 0.6460 | 0.4392 | 0.060* | |
H28F | 0.1436 | 0.5221 | 0.4205 | 0.060* | |
C25 | 0.2648 (4) | 0.5711 (4) | 0.5839 (3) | 0.0378 (11) | |
H25C | 0.3255 | 0.5894 | 0.5487 | 0.045* | |
H25D | 0.1952 | 0.6472 | 0.5835 | 0.045* | |
C26 | 0.3257 (4) | 0.5035 (4) | 0.6747 (3) | 0.0328 (10) | |
O26 | 0.2924 (3) | 0.5399 (3) | 0.7358 (2) | 0.0480 (9) | |
C31 | 0.6331 (4) | 0.2494 (3) | 0.7869 (2) | 0.0277 (9) | |
C32 | 0.7058 (4) | 0.3126 (4) | 0.7741 (3) | 0.0314 (9) | |
Cl2 | 0.63358 (10) | 0.46609 (9) | 0.75792 (8) | 0.0422 (3) | |
C33 | 0.8314 (4) | 0.2639 (4) | 0.7732 (3) | 0.0389 (11) | |
H33 | 0.8744 | 0.3125 | 0.7628 | 0.047* | |
C34 | 0.8954 (4) | 0.1423 (4) | 0.7876 (3) | 0.0429 (11) | |
H34 | 0.9826 | 0.1066 | 0.7864 | 0.052* | |
C35 | 0.8303 (4) | 0.0745 (4) | 0.8037 (3) | 0.0381 (11) | |
H35 | 0.8732 | −0.0089 | 0.8146 | 0.046* | |
C36 | 0.7035 (4) | 0.1263 (4) | 0.8042 (3) | 0.0341 (10) | |
Cl6 | 0.63513 (11) | 0.02788 (9) | 0.82867 (8) | 0.0406 (3) | |
C1A | 0.3396 (4) | 0.8963 (3) | 0.6989 (2) | 0.0267 (9) | |
H1A | 0.2986 | 0.9691 | 0.7180 | 0.032* | |
C11A | 0.4774 (4) | 0.8648 (3) | 0.7046 (2) | 0.0257 (9) | |
C12A | 0.5592 (4) | 0.7733 (4) | 0.7702 (3) | 0.0272 (9) | |
O12A | 0.5274 (2) | 0.7055 (2) | 0.83566 (18) | 0.0318 (7) | |
C13A | 0.6947 (4) | 0.7390 (4) | 0.7814 (3) | 0.0315 (9) | |
H13A | 0.7388 | 0.6516 | 0.8053 | 0.038* | |
H13B | 0.7124 | 0.7737 | 0.8245 | 0.038* | |
C14A | 0.7474 (4) | 0.7773 (4) | 0.6994 (3) | 0.0310 (9) | |
C17A | 0.8761 (4) | 0.7653 (4) | 0.7239 (3) | 0.0417 (11) | |
H17A | 0.9106 | 0.7900 | 0.6714 | 0.063* | |
H17B | 0.9301 | 0.6824 | 0.7553 | 0.063* | |
H17C | 0.8706 | 0.8156 | 0.7607 | 0.063* | |
C18A | 0.7580 (4) | 0.6982 (4) | 0.6421 (3) | 0.0409 (11) | |
H18A | 0.6756 | 0.7045 | 0.6263 | 0.061* | |
H18B | 0.8132 | 0.6157 | 0.6735 | 0.061* | |
H18C | 0.7921 | 0.7237 | 0.5896 | 0.061* | |
C15A | 0.6587 (4) | 0.9071 (4) | 0.6500 (3) | 0.0324 (10) | |
H15A | 0.6778 | 0.9597 | 0.6761 | 0.039* | |
H15B | 0.6774 | 0.9232 | 0.5897 | 0.039* | |
C16A | 0.5222 (4) | 0.9409 (4) | 0.6480 (3) | 0.0298 (9) | |
O16A | 0.4482 (3) | 1.0390 (2) | 0.59961 (19) | 0.0363 (7) | |
C21A | 0.3180 (3) | 0.7969 (3) | 0.7630 (2) | 0.0256 (8) | |
H21A | 0.3458 | 0.7282 | 0.7388 | 0.031* | |
C22A | 0.3979 (4) | 0.7555 (4) | 0.8492 (3) | 0.0300 (9) | |
O22A | 0.3734 (3) | 0.8548 (2) | 0.87668 (18) | 0.0320 (7) | |
H22A | 0.4107 | 0.8334 | 0.9266 | 0.038* | |
C23A | 0.3829 (4) | 0.6553 (4) | 0.9144 (3) | 0.0328 (10) | |
H23A | 0.4338 | 0.6353 | 0.9697 | 0.039* | |
H23B | 0.4155 | 0.5844 | 0.8936 | 0.039* | |
C24A | 0.2488 (4) | 0.6839 (4) | 0.9312 (3) | 0.0338 (10) | |
C27A | 0.2441 (5) | 0.5682 (5) | 0.9845 (3) | 0.0523 (13) | |
H27A | 0.1588 | 0.5847 | 0.9961 | 0.078* | |
H27B | 0.2987 | 0.5362 | 1.0393 | 0.078* | |
H27C | 0.2719 | 0.5101 | 0.9520 | 0.078* | |
C28A | 0.1992 (4) | 0.7749 (5) | 0.9819 (3) | 0.0469 (12) | |
H28A | 0.1131 | 0.7903 | 0.9907 | 0.070* | |
H28B | 0.2023 | 0.8489 | 0.9492 | 0.070* | |
H28C | 0.2504 | 0.7435 | 1.0380 | 0.070* | |
C25A | 0.1652 (4) | 0.7321 (4) | 0.8448 (3) | 0.0327 (10) | |
H25A | 0.1811 | 0.6657 | 0.8204 | 0.039* | |
H25B | 0.0774 | 0.7636 | 0.8556 | 0.039* | |
C26A | 0.1841 (4) | 0.8280 (4) | 0.7793 (3) | 0.0292 (9) | |
O26A | 0.0997 (3) | 0.9216 (3) | 0.7402 (2) | 0.0428 (8) | |
C31A | 0.2781 (4) | 0.9254 (4) | 0.6079 (3) | 0.0287 (9) | |
C32A | 0.1761 (4) | 1.0334 (4) | 0.5675 (3) | 0.0321 (10) | |
Cl3A | 0.12852 (11) | 1.14906 (10) | 0.61450 (8) | 0.0473 (3) | |
C33A | 0.1093 (4) | 1.0563 (4) | 0.4905 (3) | 0.0389 (11) | |
H33A | 0.0386 | 1.1298 | 0.4673 | 0.047* | |
C34A | 0.1455 (4) | 0.9715 (4) | 0.4463 (3) | 0.0394 (11) | |
H34A | 0.0983 | 0.9856 | 0.3938 | 0.047* | |
C35A | 0.2503 (4) | 0.8670 (4) | 0.4796 (3) | 0.0362 (10) | |
H35A | 0.2791 | 0.8102 | 0.4486 | 0.043* | |
C36A | 0.3132 (4) | 0.8454 (3) | 0.5583 (3) | 0.0270 (9) | |
Cl6A | 0.44433 (9) | 0.71079 (9) | 0.59683 (7) | 0.0333 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.040 (2) | 0.023 (2) | 0.025 (2) | −0.0160 (18) | 0.0064 (18) | −0.0102 (17) |
C11 | 0.036 (2) | 0.029 (2) | 0.032 (2) | −0.0148 (18) | 0.0110 (18) | −0.0159 (19) |
C12 | 0.037 (2) | 0.027 (2) | 0.032 (2) | −0.0159 (18) | 0.0103 (18) | −0.0144 (18) |
O12 | 0.0428 (17) | 0.0320 (16) | 0.0299 (16) | −0.0214 (14) | 0.0054 (13) | −0.0114 (13) |
C13 | 0.048 (3) | 0.041 (3) | 0.037 (3) | −0.028 (2) | 0.009 (2) | −0.016 (2) |
C14 | 0.039 (2) | 0.046 (3) | 0.035 (3) | −0.021 (2) | 0.013 (2) | −0.019 (2) |
C17 | 0.052 (3) | 0.076 (4) | 0.041 (3) | −0.039 (3) | 0.013 (2) | −0.013 (3) |
C18 | 0.049 (3) | 0.061 (4) | 0.075 (4) | −0.023 (3) | 0.022 (3) | −0.036 (3) |
C15 | 0.049 (3) | 0.052 (3) | 0.031 (3) | −0.027 (2) | 0.011 (2) | −0.011 (2) |
C16 | 0.034 (2) | 0.039 (3) | 0.032 (2) | −0.016 (2) | 0.0043 (19) | −0.013 (2) |
O16 | 0.052 (2) | 0.059 (2) | 0.0290 (17) | −0.0311 (18) | 0.0027 (15) | −0.0143 (16) |
C21 | 0.033 (2) | 0.022 (2) | 0.032 (2) | −0.0145 (17) | 0.0085 (17) | −0.0130 (18) |
C22 | 0.030 (2) | 0.025 (2) | 0.031 (2) | −0.0123 (17) | 0.0084 (17) | −0.0128 (18) |
O22 | 0.0394 (16) | 0.0199 (15) | 0.0400 (18) | −0.0064 (13) | 0.0030 (13) | −0.0162 (13) |
C23 | 0.034 (2) | 0.025 (2) | 0.029 (2) | −0.0126 (18) | 0.0066 (17) | −0.0118 (18) |
C24 | 0.033 (2) | 0.023 (2) | 0.040 (3) | −0.0090 (18) | 0.0017 (19) | −0.0140 (19) |
C27 | 0.034 (2) | 0.050 (3) | 0.049 (3) | −0.012 (2) | 0.003 (2) | −0.020 (2) |
C28 | 0.040 (3) | 0.031 (2) | 0.043 (3) | −0.008 (2) | 0.000 (2) | −0.013 (2) |
C25 | 0.039 (2) | 0.026 (2) | 0.047 (3) | −0.0091 (19) | −0.001 (2) | −0.016 (2) |
C26 | 0.034 (2) | 0.026 (2) | 0.043 (3) | −0.0129 (18) | 0.0043 (19) | −0.019 (2) |
O26 | 0.052 (2) | 0.0377 (19) | 0.054 (2) | −0.0080 (15) | 0.0041 (16) | −0.0307 (17) |
C31 | 0.033 (2) | 0.026 (2) | 0.025 (2) | −0.0115 (17) | 0.0041 (17) | −0.0109 (17) |
C32 | 0.040 (2) | 0.029 (2) | 0.031 (2) | −0.0175 (19) | 0.0063 (19) | −0.0144 (19) |
Cl2 | 0.0454 (7) | 0.0272 (6) | 0.0587 (8) | −0.0191 (5) | 0.0044 (5) | −0.0142 (5) |
C33 | 0.046 (3) | 0.037 (3) | 0.036 (3) | −0.020 (2) | 0.008 (2) | −0.011 (2) |
C34 | 0.034 (2) | 0.044 (3) | 0.046 (3) | −0.010 (2) | 0.007 (2) | −0.018 (2) |
C35 | 0.041 (3) | 0.028 (2) | 0.041 (3) | −0.009 (2) | 0.001 (2) | −0.013 (2) |
C36 | 0.050 (3) | 0.026 (2) | 0.030 (2) | −0.018 (2) | 0.003 (2) | −0.0112 (18) |
Cl6 | 0.0541 (7) | 0.0259 (6) | 0.0451 (7) | −0.0190 (5) | 0.0074 (5) | −0.0124 (5) |
C1A | 0.036 (2) | 0.020 (2) | 0.024 (2) | −0.0090 (17) | 0.0041 (17) | −0.0103 (17) |
C11A | 0.033 (2) | 0.021 (2) | 0.027 (2) | −0.0110 (17) | 0.0073 (17) | −0.0137 (17) |
C12A | 0.031 (2) | 0.027 (2) | 0.031 (2) | −0.0149 (18) | 0.0096 (18) | −0.0170 (18) |
O12A | 0.0305 (15) | 0.0248 (15) | 0.0379 (17) | −0.0103 (12) | 0.0059 (13) | −0.0083 (13) |
C13A | 0.033 (2) | 0.025 (2) | 0.034 (2) | −0.0100 (18) | 0.0004 (18) | −0.0100 (19) |
C14A | 0.032 (2) | 0.028 (2) | 0.036 (2) | −0.0141 (18) | 0.0078 (18) | −0.0144 (19) |
C17A | 0.039 (3) | 0.038 (3) | 0.047 (3) | −0.017 (2) | 0.005 (2) | −0.012 (2) |
C18A | 0.039 (2) | 0.046 (3) | 0.049 (3) | −0.019 (2) | 0.012 (2) | −0.030 (2) |
C15A | 0.038 (2) | 0.029 (2) | 0.038 (2) | −0.0190 (19) | 0.0067 (19) | −0.0127 (19) |
C16A | 0.043 (2) | 0.024 (2) | 0.027 (2) | −0.0167 (19) | 0.0012 (18) | −0.0111 (18) |
O16A | 0.0408 (17) | 0.0244 (16) | 0.0419 (18) | −0.0133 (14) | 0.0025 (14) | −0.0086 (14) |
C21A | 0.031 (2) | 0.0201 (19) | 0.027 (2) | −0.0100 (17) | 0.0022 (17) | −0.0098 (17) |
C22A | 0.031 (2) | 0.027 (2) | 0.036 (2) | −0.0121 (18) | 0.0099 (18) | −0.0162 (19) |
O22A | 0.0412 (17) | 0.0285 (16) | 0.0297 (16) | −0.0141 (13) | 0.0032 (13) | −0.0155 (13) |
C23A | 0.036 (2) | 0.026 (2) | 0.033 (2) | −0.0124 (18) | 0.0047 (19) | −0.0057 (19) |
C24A | 0.038 (2) | 0.036 (2) | 0.032 (2) | −0.019 (2) | 0.0061 (19) | −0.013 (2) |
C27A | 0.052 (3) | 0.055 (3) | 0.052 (3) | −0.033 (3) | 0.013 (2) | −0.003 (3) |
C28A | 0.049 (3) | 0.065 (3) | 0.042 (3) | −0.032 (3) | 0.015 (2) | −0.030 (3) |
C25A | 0.036 (2) | 0.037 (2) | 0.032 (2) | −0.019 (2) | 0.0111 (18) | −0.015 (2) |
C26A | 0.030 (2) | 0.031 (2) | 0.030 (2) | −0.0127 (19) | 0.0045 (18) | −0.0161 (19) |
O26A | 0.0307 (17) | 0.0360 (19) | 0.049 (2) | −0.0043 (14) | 0.0091 (14) | −0.0090 (16) |
C31A | 0.031 (2) | 0.028 (2) | 0.029 (2) | −0.0154 (18) | 0.0050 (17) | −0.0081 (18) |
C32A | 0.028 (2) | 0.028 (2) | 0.037 (3) | −0.0108 (18) | 0.0067 (19) | −0.0078 (19) |
Cl3A | 0.0489 (7) | 0.0276 (6) | 0.0539 (8) | −0.0037 (5) | 0.0053 (6) | −0.0153 (5) |
C33A | 0.030 (2) | 0.040 (3) | 0.041 (3) | −0.014 (2) | 0.003 (2) | −0.005 (2) |
C34A | 0.041 (3) | 0.050 (3) | 0.029 (2) | −0.027 (2) | −0.001 (2) | −0.003 (2) |
C35A | 0.044 (3) | 0.045 (3) | 0.032 (2) | −0.028 (2) | 0.012 (2) | −0.017 (2) |
C36A | 0.030 (2) | 0.024 (2) | 0.032 (2) | −0.0145 (17) | 0.0034 (17) | −0.0097 (18) |
Cl6A | 0.0358 (6) | 0.0302 (5) | 0.0390 (6) | −0.0129 (4) | 0.0081 (4) | −0.0201 (5) |
C1—C31 | 1.508 (5) | C1A—C11A | 1.517 (5) |
C1—C11 | 1.510 (6) | C1A—C31A | 1.523 (5) |
C1—C21 | 1.546 (6) | C1A—C21A | 1.539 (5) |
C1—H1 | 1.0000 | C1A—H1A | 1.0000 |
C11—C12 | 1.337 (6) | C11A—C12A | 1.360 (6) |
C11—C16 | 1.437 (6) | C11A—C16A | 1.435 (6) |
C12—O12 | 1.349 (5) | C12A—O12A | 1.350 (5) |
C12—C13 | 1.501 (6) | C12A—C13A | 1.485 (6) |
O12—C22 | 1.460 (5) | O12A—C22A | 1.451 (5) |
C13—C14 | 1.532 (6) | C13A—C14A | 1.523 (6) |
C13—H13C | 0.9900 | C13A—H13A | 0.9900 |
C13—H13D | 0.9900 | C13A—H13B | 0.9900 |
C14—C15 | 1.519 (6) | C14A—C17A | 1.518 (6) |
C14—C18 | 1.529 (7) | C14A—C18A | 1.528 (6) |
C14—C17 | 1.533 (7) | C14A—C15A | 1.547 (6) |
C17—H17D | 0.9800 | C17A—H17A | 0.9800 |
C17—H17E | 0.9800 | C17A—H17B | 0.9800 |
C17—H17F | 0.9800 | C17A—H17C | 0.9800 |
C18—H18D | 0.9800 | C18A—H18A | 0.9800 |
C18—H18E | 0.9800 | C18A—H18B | 0.9800 |
C18—H18F | 0.9800 | C18A—H18C | 0.9800 |
C15—C16 | 1.494 (6) | C15A—C16A | 1.499 (6) |
C15—H15C | 0.9900 | C15A—H15A | 0.9900 |
C15—H15D | 0.9900 | C15A—H15B | 0.9900 |
C16—O16 | 1.232 (5) | C16A—O16A | 1.242 (5) |
C21—C26 | 1.520 (5) | C21A—C22A | 1.522 (6) |
C21—C22 | 1.528 (5) | C21A—C26A | 1.521 (5) |
C21—H21 | 1.0000 | C21A—H21A | 1.0000 |
C22—O22 | 1.392 (4) | C22A—O22A | 1.393 (5) |
C22—C23 | 1.514 (6) | C22A—C23A | 1.516 (6) |
O22—H22 | 0.8400 | O22A—H22A | 0.8400 |
C23—C24 | 1.548 (5) | C23A—C24A | 1.529 (6) |
C23—H23C | 0.9900 | C23A—H23A | 0.9900 |
C23—H23D | 0.9900 | C23A—H23B | 0.9900 |
C24—C28 | 1.524 (6) | C24A—C25A | 1.534 (6) |
C24—C27 | 1.527 (6) | C24A—C28A | 1.536 (6) |
C24—C25 | 1.534 (6) | C24A—C27A | 1.542 (6) |
C27—H27D | 0.9800 | C27A—H27A | 0.9800 |
C27—H27E | 0.9800 | C27A—H27B | 0.9800 |
C27—H27F | 0.9800 | C27A—H27C | 0.9800 |
C28—H28D | 0.9800 | C28A—H28A | 0.9800 |
C28—H28E | 0.9800 | C28A—H28B | 0.9800 |
C28—H28F | 0.9800 | C28A—H28C | 0.9800 |
C25—C26 | 1.496 (6) | C25A—C26A | 1.500 (6) |
C25—H25C | 0.9900 | C25A—H25A | 0.9900 |
C25—H25D | 0.9900 | C25A—H25B | 0.9900 |
C26—O26 | 1.207 (5) | C26A—O26A | 1.209 (5) |
C31—C32 | 1.402 (6) | C31A—C32A | 1.402 (6) |
C31—C36 | 1.408 (6) | C31A—C36A | 1.409 (5) |
C32—C33 | 1.366 (6) | C32A—C33A | 1.371 (6) |
C32—Cl2 | 1.752 (4) | C32A—Cl3A | 1.750 (4) |
C33—C34 | 1.388 (6) | C33A—C34A | 1.391 (6) |
C33—H33 | 0.9500 | C33A—H33A | 0.9500 |
C34—C35 | 1.374 (7) | C34A—C35A | 1.376 (6) |
C34—H34 | 0.9500 | C34A—H34A | 0.9500 |
C35—C36 | 1.379 (6) | C35A—C36A | 1.377 (6) |
C35—H35 | 0.9500 | C35A—H35A | 0.9500 |
C36—Cl6 | 1.746 (4) | C36A—Cl6A | 1.742 (4) |
C31—C1—C11 | 119.4 (3) | C11A—C1A—C31A | 114.0 (3) |
C31—C1—C21 | 111.8 (3) | C11A—C1A—C21A | 109.7 (3) |
C11—C1—C21 | 108.7 (3) | C31A—C1A—C21A | 111.6 (3) |
C31—C1—H1 | 105.2 | C11A—C1A—H1A | 107.1 |
C11—C1—H1 | 105.2 | C31A—C1A—H1A | 107.1 |
C21—C1—H1 | 105.2 | C21A—C1A—H1A | 107.1 |
C12—C11—C16 | 119.2 (4) | C12A—C11A—C16A | 117.9 (4) |
C12—C11—C1 | 122.8 (4) | C12A—C11A—C1A | 121.1 (3) |
C16—C11—C1 | 117.9 (4) | C16A—C11A—C1A | 120.4 (3) |
C11—C12—O12 | 124.7 (4) | O12A—C12A—C11A | 124.6 (3) |
C11—C12—C13 | 124.5 (4) | O12A—C12A—C13A | 111.1 (3) |
O12—C12—C13 | 110.8 (3) | C11A—C12A—C13A | 124.2 (4) |
C12—O12—C22 | 118.3 (3) | C12A—O12A—C22A | 115.7 (3) |
C12—C13—C14 | 112.3 (4) | C12A—C13A—C14A | 115.1 (3) |
C12—C13—H13C | 109.1 | C12A—C13A—H13A | 108.5 |
C14—C13—H13C | 109.1 | C14A—C13A—H13A | 108.5 |
C12—C13—H13D | 109.1 | C12A—C13A—H13B | 108.5 |
C14—C13—H13D | 109.1 | C14A—C13A—H13B | 108.5 |
H13C—C13—H13D | 107.9 | H13A—C13A—H13B | 107.5 |
C15—C14—C18 | 110.0 (4) | C17A—C14A—C13A | 109.0 (4) |
C15—C14—C13 | 107.5 (4) | C17A—C14A—C18A | 108.7 (3) |
C18—C14—C13 | 110.3 (4) | C13A—C14A—C18A | 110.3 (4) |
C15—C14—C17 | 110.2 (4) | C17A—C14A—C15A | 111.2 (3) |
C18—C14—C17 | 109.8 (4) | C13A—C14A—C15A | 108.5 (3) |
C13—C14—C17 | 109.0 (4) | C18A—C14A—C15A | 109.3 (4) |
C14—C17—H17D | 109.5 | C14A—C17A—H17A | 109.5 |
C14—C17—H17E | 109.5 | C14A—C17A—H17B | 109.5 |
H17D—C17—H17E | 109.5 | H17A—C17A—H17B | 109.5 |
C14—C17—H17F | 109.5 | C14A—C17A—H17C | 109.5 |
H17D—C17—H17F | 109.5 | H17A—C17A—H17C | 109.5 |
H17E—C17—H17F | 109.5 | H17B—C17A—H17C | 109.5 |
C14—C18—H18D | 109.5 | C14A—C18A—H18A | 109.5 |
C14—C18—H18E | 109.5 | C14A—C18A—H18B | 109.5 |
H18D—C18—H18E | 109.5 | H18A—C18A—H18B | 109.5 |
C14—C18—H18F | 109.5 | C14A—C18A—H18C | 109.5 |
H18D—C18—H18F | 109.5 | H18A—C18A—H18C | 109.5 |
H18E—C18—H18F | 109.5 | H18B—C18A—H18C | 109.5 |
C16—C15—C14 | 115.3 (4) | C16A—C15A—C14A | 116.9 (3) |
C16—C15—H15C | 108.4 | C16A—C15A—H15A | 108.1 |
C14—C15—H15C | 108.4 | C14A—C15A—H15A | 108.1 |
C16—C15—H15D | 108.4 | C16A—C15A—H15B | 108.1 |
C14—C15—H15D | 108.4 | C14A—C15A—H15B | 108.1 |
H15C—C15—H15D | 107.5 | H15A—C15A—H15B | 107.3 |
O16—C16—C11 | 120.3 (4) | O16A—C16A—C11A | 120.4 (4) |
O16—C16—C15 | 120.8 (4) | O16A—C16A—C15A | 118.8 (4) |
C11—C16—C15 | 118.9 (4) | C11A—C16A—C15A | 120.7 (4) |
C26—C21—C22 | 109.9 (3) | C22A—C21A—C26A | 108.6 (3) |
C26—C21—C1 | 112.8 (3) | C22A—C21A—C1A | 110.3 (3) |
C22—C21—C1 | 112.4 (3) | C26A—C21A—C1A | 115.4 (3) |
C26—C21—H21 | 107.1 | C22A—C21A—H21A | 107.4 |
C22—C21—H21 | 107.1 | C26A—C21A—H21A | 107.4 |
C1—C21—H21 | 107.1 | C1A—C21A—H21A | 107.4 |
O22—C22—O12 | 108.8 (3) | O22A—C22A—O12A | 108.3 (3) |
O22—C22—C23 | 112.0 (3) | O22A—C22A—C23A | 114.6 (3) |
O12—C22—C23 | 104.5 (3) | O12A—C22A—C23A | 104.8 (3) |
O22—C22—C21 | 107.6 (3) | O22A—C22A—C21A | 107.7 (3) |
O12—C22—C21 | 110.1 (3) | O12A—C22A—C21A | 108.5 (3) |
C23—C22—C21 | 113.7 (3) | C23A—C22A—C21A | 112.7 (3) |
C22—O22—H22 | 109.5 | C22A—O22A—H22A | 109.5 |
C22—C23—C24 | 116.9 (3) | C22A—C23A—C24A | 114.0 (3) |
C22—C23—H23C | 108.1 | C22A—C23A—H23A | 108.7 |
C24—C23—H23C | 108.1 | C24A—C23A—H23A | 108.7 |
C22—C23—H23D | 108.1 | C22A—C23A—H23B | 108.7 |
C24—C23—H23D | 108.1 | C24A—C23A—H23B | 108.7 |
H23C—C23—H23D | 107.3 | H23A—C23A—H23B | 107.6 |
C28—C24—C27 | 110.0 (4) | C23A—C24A—C25A | 109.4 (3) |
C28—C24—C25 | 108.9 (4) | C23A—C24A—C28A | 112.7 (4) |
C27—C24—C25 | 109.6 (4) | C25A—C24A—C28A | 109.0 (4) |
C28—C24—C23 | 108.2 (3) | C23A—C24A—C27A | 108.2 (4) |
C27—C24—C23 | 112.1 (4) | C25A—C24A—C27A | 109.2 (4) |
C25—C24—C23 | 108.0 (3) | C28A—C24A—C27A | 108.3 (4) |
C24—C27—H27D | 109.5 | C24A—C27A—H27A | 109.5 |
C24—C27—H27E | 109.5 | C24A—C27A—H27B | 109.5 |
H27D—C27—H27E | 109.5 | H27A—C27A—H27B | 109.5 |
C24—C27—H27F | 109.5 | C24A—C27A—H27C | 109.5 |
H27D—C27—H27F | 109.5 | H27A—C27A—H27C | 109.5 |
H27E—C27—H27F | 109.5 | H27B—C27A—H27C | 109.5 |
C24—C28—H28D | 109.5 | C24A—C28A—H28A | 109.5 |
C24—C28—H28E | 109.5 | C24A—C28A—H28B | 109.5 |
H28D—C28—H28E | 109.5 | H28A—C28A—H28B | 109.5 |
C24—C28—H28F | 109.5 | C24A—C28A—H28C | 109.5 |
H28D—C28—H28F | 109.5 | H28A—C28A—H28C | 109.5 |
H28E—C28—H28F | 109.5 | H28B—C28A—H28C | 109.5 |
C26—C25—C24 | 112.0 (4) | C26A—C25A—C24A | 114.0 (3) |
C26—C25—H25C | 109.2 | C26A—C25A—H25A | 108.7 |
C24—C25—H25C | 109.2 | C24A—C25A—H25A | 108.7 |
C26—C25—H25D | 109.2 | C26A—C25A—H25B | 108.7 |
C24—C25—H25D | 109.2 | C24A—C25A—H25B | 108.7 |
H25C—C25—H25D | 107.9 | H25A—C25A—H25B | 107.6 |
O26—C26—C25 | 123.3 (4) | O26A—C26A—C25A | 123.1 (4) |
O26—C26—C21 | 121.9 (4) | O26A—C26A—C21A | 122.0 (4) |
C25—C26—C21 | 114.8 (4) | C25A—C26A—C21A | 114.8 (3) |
C32—C31—C36 | 113.2 (4) | C32A—C31A—C36A | 113.6 (4) |
C32—C31—C1 | 118.6 (4) | C32A—C31A—C1A | 122.5 (4) |
C36—C31—C1 | 128.2 (4) | C36A—C31A—C1A | 123.8 (4) |
C33—C32—C31 | 125.1 (4) | C33A—C32A—C31A | 123.7 (4) |
C33—C32—Cl2 | 115.9 (3) | C33A—C32A—Cl3A | 116.2 (3) |
C31—C32—Cl2 | 119.0 (3) | C31A—C32A—Cl3A | 120.1 (3) |
C32—C33—C34 | 119.1 (4) | C32A—C33A—C34A | 119.8 (4) |
C32—C33—H33 | 120.4 | C32A—C33A—H33A | 120.1 |
C34—C33—H33 | 120.4 | C34A—C33A—H33A | 120.1 |
C35—C34—C33 | 118.8 (4) | C35A—C34A—C33A | 119.2 (4) |
C35—C34—H34 | 120.6 | C35A—C34A—H34A | 120.4 |
C33—C34—H34 | 120.6 | C33A—C34A—H34A | 120.4 |
C34—C35—C36 | 120.8 (4) | C34A—C35A—C36A | 119.5 (4) |
C34—C35—H35 | 119.6 | C34A—C35A—H35A | 120.3 |
C36—C35—H35 | 119.6 | C36A—C35A—H35A | 120.3 |
C35—C36—C31 | 123.0 (4) | C35A—C36A—C31A | 124.0 (4) |
C35—C36—Cl6 | 115.2 (3) | C35A—C36A—Cl6A | 116.9 (3) |
C31—C36—Cl6 | 121.8 (3) | C31A—C36A—Cl6A | 119.1 (3) |
C31—C1—C11—C12 | −116.6 (4) | C31A—C1A—C11A—C12A | −137.8 (4) |
C21—C1—C11—C12 | 13.2 (5) | C21A—C1A—C11A—C12A | −11.8 (5) |
C31—C1—C11—C16 | 68.1 (5) | C31A—C1A—C11A—C16A | 51.0 (5) |
C21—C1—C11—C16 | −162.0 (3) | C21A—C1A—C11A—C16A | 176.9 (3) |
C16—C11—C12—O12 | −179.2 (4) | C16A—C11A—C12A—O12A | 169.7 (3) |
C1—C11—C12—O12 | 5.6 (6) | C1A—C11A—C12A—O12A | −1.8 (6) |
C16—C11—C12—C13 | 0.6 (6) | C16A—C11A—C12A—C13A | −6.9 (6) |
C1—C11—C12—C13 | −174.6 (4) | C1A—C11A—C12A—C13A | −178.4 (3) |
C11—C12—O12—C22 | 7.3 (6) | C11A—C12A—O12A—C22A | −18.3 (5) |
C13—C12—O12—C22 | −172.5 (3) | C13A—C12A—O12A—C22A | 158.7 (3) |
C11—C12—C13—C14 | 25.6 (6) | O12A—C12A—C13A—C14A | 159.7 (3) |
O12—C12—C13—C14 | −154.6 (4) | C11A—C12A—C13A—C14A | −23.3 (6) |
C12—C13—C14—C15 | −48.7 (5) | C12A—C13A—C14A—C17A | 165.5 (3) |
C12—C13—C14—C18 | 71.1 (5) | C12A—C13A—C14A—C18A | −75.3 (4) |
C12—C13—C14—C17 | −168.2 (4) | C12A—C13A—C14A—C15A | 44.3 (5) |
C18—C14—C15—C16 | −68.8 (5) | C17A—C14A—C15A—C16A | −159.9 (4) |
C13—C14—C15—C16 | 51.2 (5) | C13A—C14A—C15A—C16A | −40.1 (5) |
C17—C14—C15—C16 | 169.9 (4) | C18A—C14A—C15A—C16A | 80.2 (4) |
C12—C11—C16—O16 | 178.5 (4) | C12A—C11A—C16A—O16A | −164.4 (4) |
C1—C11—C16—O16 | −6.1 (6) | C1A—C11A—C16A—O16A | 7.2 (5) |
C12—C11—C16—C15 | 0.2 (6) | C12A—C11A—C16A—C15A | 11.8 (5) |
C1—C11—C16—C15 | 175.6 (4) | C1A—C11A—C16A—C15A | −176.6 (3) |
C14—C15—C16—O16 | 153.6 (4) | C14A—C15A—C16A—O16A | −170.3 (4) |
C14—C15—C16—C11 | −28.1 (6) | C14A—C15A—C16A—C11A | 13.4 (5) |
C31—C1—C21—C26 | −144.0 (3) | C11A—C1A—C21A—C22A | 43.1 (4) |
C11—C1—C21—C26 | 82.1 (4) | C31A—C1A—C21A—C22A | 170.4 (3) |
C31—C1—C21—C22 | 91.1 (4) | C11A—C1A—C21A—C26A | 166.6 (3) |
C11—C1—C21—C22 | −42.8 (4) | C31A—C1A—C21A—C26A | −66.1 (4) |
C12—O12—C22—O22 | 80.2 (4) | C12A—O12A—C22A—O22A | −66.6 (4) |
C12—O12—C22—C23 | −160.0 (3) | C12A—O12A—C22A—C23A | 170.6 (3) |
C12—O12—C22—C21 | −37.4 (4) | C12A—O12A—C22A—C21A | 50.0 (4) |
C26—C21—C22—O22 | 170.7 (3) | C26A—C21A—C22A—O22A | −73.3 (4) |
C1—C21—C22—O22 | −62.8 (4) | C1A—C21A—C22A—O22A | 54.0 (4) |
C26—C21—C22—O12 | −70.8 (4) | C26A—C21A—C22A—O12A | 169.7 (3) |
C1—C21—C22—O12 | 55.7 (4) | C1A—C21A—C22A—O12A | −63.0 (4) |
C26—C21—C22—C23 | 46.1 (4) | C26A—C21A—C22A—C23A | 54.0 (4) |
C1—C21—C22—C23 | 172.6 (3) | C1A—C21A—C22A—C23A | −178.6 (3) |
O22—C22—C23—C24 | −169.5 (3) | O22A—C22A—C23A—C24A | 67.9 (5) |
O12—C22—C23—C24 | 72.9 (4) | O12A—C22A—C23A—C24A | −173.5 (3) |
C21—C22—C23—C24 | −47.3 (5) | C21A—C22A—C23A—C24A | −55.7 (5) |
C22—C23—C24—C28 | 166.6 (3) | C22A—C23A—C24A—C25A | 50.5 (5) |
C22—C23—C24—C27 | −72.0 (5) | C22A—C23A—C24A—C28A | −70.9 (5) |
C22—C23—C24—C25 | 48.9 (5) | C22A—C23A—C24A—C27A | 169.4 (4) |
C28—C24—C25—C26 | −170.2 (3) | C23A—C24A—C25A—C26A | −48.5 (5) |
C27—C24—C25—C26 | 69.5 (5) | C28A—C24A—C25A—C26A | 75.1 (4) |
C23—C24—C25—C26 | −53.0 (5) | C27A—C24A—C25A—C26A | −166.7 (4) |
C24—C25—C26—O26 | −121.5 (5) | C24A—C25A—C26A—O26A | −129.9 (4) |
C24—C25—C26—C21 | 59.0 (5) | C24A—C25A—C26A—C21A | 52.4 (5) |
C22—C21—C26—O26 | 127.1 (4) | C22A—C21A—C26A—O26A | 129.2 (4) |
C1—C21—C26—O26 | 0.8 (6) | C1A—C21A—C26A—O26A | 4.7 (5) |
C22—C21—C26—C25 | −53.4 (5) | C22A—C21A—C26A—C25A | −53.1 (4) |
C1—C21—C26—C25 | −179.7 (3) | C1A—C21A—C26A—C25A | −177.5 (3) |
C11—C1—C31—C32 | −157.6 (4) | C11A—C1A—C31A—C32A | −123.4 (4) |
C21—C1—C31—C32 | 73.9 (4) | C21A—C1A—C31A—C32A | 111.7 (4) |
C11—C1—C31—C36 | 23.5 (6) | C11A—C1A—C31A—C36A | 60.1 (5) |
C21—C1—C31—C36 | −105.0 (5) | C21A—C1A—C31A—C36A | −64.8 (5) |
C36—C31—C32—C33 | 3.4 (6) | C36A—C31A—C32A—C33A | 5.3 (6) |
C1—C31—C32—C33 | −175.6 (4) | C1A—C31A—C32A—C33A | −171.5 (4) |
C36—C31—C32—Cl2 | −176.5 (3) | C36A—C31A—C32A—Cl3A | −173.8 (3) |
C1—C31—C32—Cl2 | 4.5 (5) | C1A—C31A—C32A—Cl3A | 9.4 (5) |
C31—C32—C33—C34 | −1.4 (7) | C31A—C32A—C33A—C34A | −2.9 (7) |
Cl2—C32—C33—C34 | 178.5 (3) | Cl3A—C32A—C33A—C34A | 176.3 (3) |
C32—C33—C34—C35 | −1.0 (7) | C32A—C33A—C34A—C35A | −1.9 (7) |
C33—C34—C35—C36 | 1.0 (7) | C33A—C34A—C35A—C36A | 3.8 (6) |
C34—C35—C36—C31 | 1.3 (7) | C34A—C35A—C36A—C31A | −1.0 (6) |
C34—C35—C36—Cl6 | −178.2 (4) | C34A—C35A—C36A—Cl6A | 179.5 (3) |
C32—C31—C36—C35 | −3.3 (6) | C32A—C31A—C36A—C35A | −3.3 (6) |
C1—C31—C36—C35 | 175.6 (4) | C1A—C31A—C36A—C35A | 173.4 (4) |
C32—C31—C36—Cl6 | 176.2 (3) | C32A—C31A—C36A—Cl6A | 176.1 (3) |
C1—C31—C36—Cl6 | −4.9 (6) | C1A—C31A—C36A—Cl6A | −7.1 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O22A—H22A···O16i | 0.84 | 1.88 | 2.721 (4) | 174 |
O22—H22···O16Aii | 0.84 | 1.96 | 2.799 (4) | 176 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, y−1, z. |
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