Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680700342X/ci2281sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680700342X/ci2281Isup2.hkl |
CCDC reference: 636217
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
C20H10Cl2O2 | F(000) = 1440 |
Mr = 353.18 | Dx = 1.507 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 9833 reflections |
a = 16.0627 (2) Å | θ = 2.5–37.5° |
b = 8.0482 (1) Å | µ = 0.43 mm−1 |
c = 24.0821 (3) Å | T = 100 K |
V = 3113.23 (7) Å3 | Block, orange |
Z = 8 | 0.47 × 0.41 × 0.30 mm |
Bruker SMART APEX2 CCD area-detector diffractometer | 16384 independent reflections |
Radiation source: fine-focus sealed tube | 15176 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 8.33 pixels mm-1 | θmax = 37.5°, θmin = 2.5° |
ω scans | h = −27→27 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −13→13 |
Tmin = 0.822, Tmax = 0.883 | l = −41→41 |
127742 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.0511P)2 + 0.4718P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
16384 reflections | Δρmax = 0.55 e Å−3 |
434 parameters | Δρmin = −0.27 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 8036 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.54 (2) |
Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
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 | ||
Cl1A | 0.473786 (14) | 0.40500 (3) | 0.089027 (10) | 0.01672 (4) | |
Cl2A | 0.585614 (16) | 0.08227 (3) | 0.095918 (11) | 0.01891 (5) | |
O1A | 0.57237 (5) | 0.67058 (10) | 0.13291 (3) | 0.01744 (13) | |
O2A | 0.76456 (5) | 0.15335 (9) | 0.10348 (4) | 0.01949 (14) | |
C1A | 0.58036 (6) | 0.43142 (11) | 0.07289 (4) | 0.01231 (14) | |
C2A | 0.61648 (6) | 0.57327 (11) | 0.10748 (4) | 0.01251 (14) | |
C3A | 0.70816 (6) | 0.58874 (10) | 0.10692 (4) | 0.01193 (13) | |
C4A | 0.74310 (6) | 0.74536 (11) | 0.11503 (4) | 0.01455 (15) | |
H4AA | 0.7090 | 0.8379 | 0.1192 | 0.017* | |
C5A | 0.82928 (7) | 0.76281 (12) | 0.11682 (4) | 0.01653 (16) | |
H5AA | 0.8528 | 0.8676 | 0.1212 | 0.020* | |
C6A | 0.88034 (6) | 0.62328 (13) | 0.11207 (4) | 0.01710 (16) | |
H6AA | 0.9379 | 0.6350 | 0.1139 | 0.021* | |
C7A | 0.84550 (6) | 0.46661 (12) | 0.10457 (4) | 0.01638 (16) | |
H7AA | 0.8798 | 0.3740 | 0.1016 | 0.020* | |
C8A | 0.75932 (6) | 0.44790 (11) | 0.10144 (4) | 0.01225 (13) | |
C9A | 0.72343 (6) | 0.27804 (11) | 0.09548 (4) | 0.01342 (14) | |
C10A | 0.63474 (6) | 0.26559 (11) | 0.07191 (4) | 0.01319 (14) | |
C11A | 0.63711 (6) | 0.28848 (12) | 0.00978 (4) | 0.01594 (16) | |
H11A | 0.6707 | 0.2271 | −0.0138 | 0.019* | |
C12A | 0.59559 (6) | 0.43469 (12) | 0.01028 (4) | 0.01380 (14) | |
C13A | 0.57228 (6) | 0.56193 (13) | −0.02984 (4) | 0.01625 (16) | |
C14A | 0.58093 (7) | 0.53649 (14) | −0.08757 (4) | 0.01779 (16) | |
C15A | 0.56186 (8) | 0.66640 (16) | −0.12426 (5) | 0.0247 (2) | |
H15A | 0.5676 | 0.6500 | −0.1623 | 0.030* | |
C16A | 0.53456 (10) | 0.81897 (16) | −0.10457 (5) | 0.0296 (2) | |
H16A | 0.5222 | 0.9041 | −0.1293 | 0.036* | |
C17A | 0.52571 (10) | 0.84445 (17) | −0.04775 (6) | 0.0307 (3) | |
H17A | 0.5080 | 0.9471 | −0.0345 | 0.037* | |
C18A | 0.54339 (8) | 0.71601 (14) | −0.01067 (5) | 0.0234 (2) | |
H18A | 0.5359 | 0.7328 | 0.0272 | 0.028* | |
C19A | 0.61027 (7) | 0.38237 (15) | −0.10979 (4) | 0.02106 (18) | |
C20A | 0.63533 (9) | 0.25598 (18) | −0.13042 (5) | 0.0288 (2) | |
H20A | 0.6678 | 0.1695 | −0.1481 | 0.035* | |
Cl1B | 0.251036 (14) | 0.90536 (3) | 0.252170 (10) | 0.01558 (4) | |
Cl2B | 0.138278 (16) | 0.58520 (3) | 0.247490 (12) | 0.01898 (5) | |
O1B | 0.15336 (5) | 1.17567 (10) | 0.21153 (4) | 0.01857 (13) | |
O2B | −0.04078 (5) | 0.65792 (9) | 0.24103 (4) | 0.02020 (14) | |
C1B | 0.14500 (6) | 0.93362 (11) | 0.26998 (4) | 0.01226 (14) | |
C2B | 0.10914 (6) | 1.07745 (11) | 0.23605 (4) | 0.01248 (14) | |
C3B | 0.01730 (6) | 1.09214 (10) | 0.23564 (4) | 0.01132 (13) | |
C4B | −0.01748 (6) | 1.24941 (11) | 0.22730 (4) | 0.01385 (14) | |
H4BA | 0.0168 | 1.3418 | 0.2233 | 0.017* | |
C5B | −0.10347 (7) | 1.26699 (13) | 0.22503 (4) | 0.01637 (16) | |
H5BA | −0.1268 | 1.3718 | 0.2204 | 0.020* | |
C6B | −0.15490 (6) | 1.12810 (13) | 0.22962 (4) | 0.01716 (16) | |
H6BA | −0.2124 | 1.1405 | 0.2275 | 0.021* | |
C7B | −0.12057 (6) | 0.97100 (12) | 0.23728 (4) | 0.01477 (15) | |
H7BA | −0.1551 | 0.8786 | 0.2401 | 0.018* | |
C8B | −0.03416 (6) | 0.95193 (11) | 0.24078 (4) | 0.01205 (13) | |
C9B | 0.00084 (6) | 0.78230 (11) | 0.24803 (4) | 0.01283 (13) | |
C10B | 0.08953 (6) | 0.76985 (11) | 0.27118 (4) | 0.01289 (14) | |
C11B | 0.08879 (6) | 0.79211 (13) | 0.33348 (4) | 0.01588 (15) | |
H11B | 0.0597 | 0.7270 | 0.3637 | 0.019* | |
C12B | 0.13224 (6) | 0.93543 (12) | 0.33297 (4) | 0.01403 (14) | |
C13B | 0.16193 (6) | 1.05498 (14) | 0.37398 (4) | 0.01755 (16) | |
C14B | 0.16783 (7) | 1.01181 (16) | 0.43092 (4) | 0.02201 (19) | |
C15B | 0.19649 (9) | 1.1299 (2) | 0.46918 (5) | 0.0312 (3) | |
H15B | 0.2009 | 1.1019 | 0.5065 | 0.037* | |
C16B | 0.21834 (9) | 1.2878 (2) | 0.45177 (7) | 0.0353 (3) | |
H16B | 0.2369 | 1.3655 | 0.4775 | 0.042* | |
C17B | 0.21270 (9) | 1.33103 (18) | 0.39600 (6) | 0.0329 (3) | |
H17B | 0.2270 | 1.4377 | 0.3846 | 0.039* | |
C18B | 0.18565 (8) | 1.21442 (15) | 0.35728 (5) | 0.0246 (2) | |
H18B | 0.1833 | 1.2429 | 0.3199 | 0.030* | |
C19B | 0.14780 (8) | 0.84852 (18) | 0.45091 (5) | 0.0264 (2) | |
C20B | 0.13319 (11) | 0.7156 (2) | 0.47028 (6) | 0.0371 (3) | |
H20B | 0.1152 | 0.6067 | 0.4851 | 0.045* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1A | 0.01191 (8) | 0.01648 (9) | 0.02175 (10) | −0.00052 (6) | 0.00153 (7) | −0.00119 (8) |
Cl2A | 0.01867 (10) | 0.01132 (8) | 0.02675 (12) | −0.00234 (7) | 0.00003 (8) | 0.00128 (8) |
O1A | 0.0165 (3) | 0.0152 (3) | 0.0207 (3) | 0.0025 (2) | 0.0030 (2) | −0.0044 (3) |
O2A | 0.0186 (3) | 0.0117 (3) | 0.0282 (4) | 0.0044 (2) | −0.0029 (3) | 0.0012 (3) |
C1A | 0.0115 (3) | 0.0124 (3) | 0.0130 (3) | 0.0004 (3) | 0.0011 (3) | −0.0001 (3) |
C2A | 0.0144 (4) | 0.0108 (3) | 0.0123 (3) | 0.0012 (3) | 0.0007 (3) | 0.0004 (3) |
C3A | 0.0130 (3) | 0.0102 (3) | 0.0126 (3) | 0.0004 (2) | 0.0002 (3) | 0.0006 (2) |
C4A | 0.0171 (4) | 0.0106 (3) | 0.0160 (4) | −0.0008 (3) | 0.0000 (3) | 0.0000 (3) |
C5A | 0.0171 (4) | 0.0139 (3) | 0.0186 (4) | −0.0042 (3) | 0.0011 (3) | 0.0011 (3) |
C6A | 0.0133 (4) | 0.0186 (4) | 0.0194 (4) | −0.0013 (3) | −0.0003 (3) | 0.0002 (3) |
C7A | 0.0149 (4) | 0.0155 (4) | 0.0187 (4) | 0.0017 (3) | 0.0000 (3) | 0.0006 (3) |
C8A | 0.0116 (3) | 0.0114 (3) | 0.0137 (3) | 0.0006 (3) | 0.0000 (3) | 0.0002 (3) |
C9A | 0.0143 (3) | 0.0110 (3) | 0.0150 (3) | 0.0010 (3) | −0.0005 (3) | 0.0002 (3) |
C10A | 0.0137 (4) | 0.0106 (3) | 0.0153 (3) | 0.0003 (3) | −0.0007 (3) | −0.0007 (3) |
C11A | 0.0183 (4) | 0.0154 (4) | 0.0141 (3) | 0.0034 (3) | −0.0004 (3) | −0.0026 (3) |
C12A | 0.0149 (3) | 0.0140 (3) | 0.0126 (3) | 0.0012 (3) | −0.0007 (3) | −0.0008 (3) |
C13A | 0.0175 (4) | 0.0170 (4) | 0.0143 (4) | 0.0030 (3) | −0.0018 (3) | 0.0006 (3) |
C14A | 0.0187 (4) | 0.0205 (4) | 0.0142 (3) | −0.0001 (3) | −0.0023 (3) | 0.0004 (3) |
C15A | 0.0313 (6) | 0.0267 (5) | 0.0161 (4) | 0.0002 (4) | −0.0050 (4) | 0.0042 (4) |
C16A | 0.0405 (7) | 0.0243 (5) | 0.0241 (5) | 0.0048 (5) | −0.0079 (5) | 0.0074 (4) |
C17A | 0.0454 (8) | 0.0215 (5) | 0.0252 (5) | 0.0123 (5) | −0.0050 (5) | 0.0032 (4) |
C18A | 0.0332 (6) | 0.0190 (4) | 0.0182 (4) | 0.0096 (4) | −0.0023 (4) | −0.0001 (3) |
C19A | 0.0244 (5) | 0.0251 (4) | 0.0137 (4) | 0.0002 (4) | −0.0012 (3) | −0.0019 (3) |
C20A | 0.0345 (6) | 0.0318 (6) | 0.0201 (5) | 0.0048 (5) | 0.0019 (4) | −0.0052 (4) |
Cl1B | 0.01107 (8) | 0.01674 (9) | 0.01895 (9) | 0.00106 (6) | 0.00072 (7) | 0.00006 (8) |
Cl2B | 0.01793 (10) | 0.01100 (8) | 0.02802 (12) | 0.00259 (7) | −0.00158 (9) | −0.00183 (8) |
O1B | 0.0153 (3) | 0.0157 (3) | 0.0247 (3) | −0.0031 (2) | 0.0026 (3) | 0.0050 (3) |
O2B | 0.0180 (3) | 0.0116 (3) | 0.0310 (4) | −0.0035 (2) | −0.0040 (3) | −0.0011 (3) |
C1B | 0.0105 (3) | 0.0119 (3) | 0.0144 (3) | −0.0007 (3) | −0.0013 (3) | 0.0003 (3) |
C2B | 0.0121 (3) | 0.0109 (3) | 0.0144 (3) | −0.0003 (3) | 0.0000 (3) | 0.0000 (3) |
C3B | 0.0111 (3) | 0.0101 (3) | 0.0127 (3) | −0.0005 (2) | 0.0001 (3) | 0.0002 (2) |
C4B | 0.0147 (4) | 0.0107 (3) | 0.0161 (4) | 0.0009 (3) | 0.0010 (3) | 0.0008 (3) |
C5B | 0.0170 (4) | 0.0150 (4) | 0.0171 (4) | 0.0041 (3) | −0.0003 (3) | 0.0018 (3) |
C6B | 0.0131 (4) | 0.0179 (4) | 0.0204 (4) | 0.0022 (3) | −0.0008 (3) | 0.0012 (3) |
C7B | 0.0121 (3) | 0.0143 (3) | 0.0179 (4) | −0.0008 (3) | −0.0011 (3) | 0.0000 (3) |
C8B | 0.0131 (3) | 0.0106 (3) | 0.0125 (3) | −0.0006 (3) | −0.0006 (3) | −0.0001 (3) |
C9B | 0.0133 (3) | 0.0106 (3) | 0.0146 (3) | −0.0014 (2) | −0.0009 (3) | −0.0003 (3) |
C10B | 0.0141 (4) | 0.0095 (3) | 0.0151 (3) | −0.0002 (3) | −0.0010 (3) | 0.0003 (3) |
C11B | 0.0170 (4) | 0.0165 (4) | 0.0141 (4) | −0.0023 (3) | −0.0016 (3) | 0.0020 (3) |
C12B | 0.0133 (3) | 0.0152 (3) | 0.0135 (3) | −0.0007 (3) | −0.0010 (3) | −0.0010 (3) |
C13B | 0.0150 (4) | 0.0206 (4) | 0.0171 (4) | −0.0023 (3) | −0.0006 (3) | −0.0048 (3) |
C14B | 0.0191 (4) | 0.0309 (5) | 0.0159 (4) | −0.0014 (4) | −0.0008 (3) | −0.0066 (4) |
C15B | 0.0284 (6) | 0.0440 (7) | 0.0212 (5) | −0.0049 (5) | −0.0017 (4) | −0.0138 (5) |
C16B | 0.0290 (6) | 0.0425 (7) | 0.0343 (6) | −0.0086 (5) | −0.0016 (5) | −0.0210 (6) |
C17B | 0.0306 (6) | 0.0289 (6) | 0.0390 (7) | −0.0119 (5) | −0.0010 (5) | −0.0137 (5) |
C18B | 0.0249 (5) | 0.0227 (5) | 0.0263 (5) | −0.0089 (4) | −0.0015 (4) | −0.0060 (4) |
C19B | 0.0276 (5) | 0.0374 (6) | 0.0142 (4) | −0.0013 (5) | −0.0022 (4) | −0.0009 (4) |
C20B | 0.0469 (8) | 0.0441 (8) | 0.0202 (5) | −0.0057 (7) | −0.0055 (5) | 0.0065 (5) |
Cl1A—C1A | 1.7682 (9) | Cl1B—C1B | 1.7711 (9) |
Cl2A—C10A | 1.7702 (10) | Cl2B—C10B | 1.7740 (10) |
O1A—C2A | 1.2208 (11) | O1B—C2B | 1.2157 (12) |
O2A—C9A | 1.2168 (11) | O2B—C9B | 1.2156 (11) |
C1A—C12A | 1.5276 (13) | C1B—C2B | 1.5295 (13) |
C1A—C2A | 1.5278 (13) | C1B—C12B | 1.5308 (14) |
C1A—C10A | 1.5952 (13) | C1B—C10B | 1.5912 (13) |
C2A—C3A | 1.4780 (13) | C2B—C3B | 1.4799 (13) |
C3A—C4A | 1.3936 (13) | C3B—C4B | 1.3981 (13) |
C3A—C8A | 1.4062 (12) | C3B—C8B | 1.4044 (12) |
C4A—C5A | 1.3921 (15) | C4B—C5B | 1.3895 (15) |
C4A—H4AA | 0.93 | C4B—H4BA | 0.93 |
C5A—C6A | 1.3952 (15) | C5B—C6B | 1.3944 (15) |
C5A—H5AA | 0.93 | C5B—H5BA | 0.93 |
C6A—C7A | 1.3913 (14) | C6B—C7B | 1.3916 (14) |
C6A—H6AA | 0.93 | C6B—H6BA | 0.93 |
C7A—C8A | 1.3945 (13) | C7B—C8B | 1.3990 (13) |
C7A—H7AA | 0.93 | C7B—H7BA | 0.93 |
C8A—C9A | 1.4906 (13) | C8B—C9B | 1.4867 (12) |
C9A—C10A | 1.5369 (13) | C9B—C10B | 1.5329 (13) |
C10A—C11A | 1.5080 (14) | C10B—C11B | 1.5111 (14) |
C11A—C12A | 1.3526 (13) | C11B—C12B | 1.3483 (14) |
C11A—H11A | 0.93 | C11B—H11B | 1.01 |
C12A—C13A | 1.4569 (14) | C12B—C13B | 1.4590 (14) |
C13A—C18A | 1.4022 (15) | C13B—C18B | 1.3976 (16) |
C13A—C14A | 1.4122 (14) | C13B—C14B | 1.4178 (15) |
C14A—C15A | 1.4027 (15) | C14B—C15B | 1.4013 (16) |
C14A—C19A | 1.4307 (16) | C14B—C19B | 1.4360 (19) |
C15A—C16A | 1.3875 (19) | C15B—C16B | 1.384 (2) |
C15A—H15A | 0.93 | C15B—H15B | 0.93 |
C16A—C17A | 1.3911 (18) | C16B—C17B | 1.390 (2) |
C16A—H16A | 0.93 | C16B—H16B | 0.93 |
C17A—C18A | 1.3951 (17) | C17B—C18B | 1.3925 (17) |
C17A—H17A | 0.93 | C17B—H17B | 0.93 |
C18A—H18A | 0.93 | C18B—H18B | 0.93 |
C19A—C20A | 1.2016 (17) | C19B—C20B | 1.190 (2) |
C20A—H20A | 0.97 | C20B—H20B | 0.99 |
C12A—C1A—C2A | 117.68 (8) | C2B—C1B—C12B | 118.15 (8) |
C12A—C1A—C10A | 84.96 (7) | C2B—C1B—C10B | 115.20 (7) |
C2A—C1A—C10A | 115.17 (8) | C12B—C1B—C10B | 85.12 (7) |
C12A—C1A—Cl1A | 111.96 (7) | C2B—C1B—Cl1B | 109.27 (6) |
C2A—C1A—Cl1A | 109.73 (6) | C12B—C1B—Cl1B | 111.71 (6) |
C10A—C1A—Cl1A | 115.64 (6) | C10B—C1B—Cl1B | 115.89 (6) |
O1A—C2A—C3A | 121.93 (9) | O1B—C2B—C3B | 121.81 (8) |
O1A—C2A—C1A | 122.18 (9) | O1B—C2B—C1B | 122.11 (9) |
C3A—C2A—C1A | 115.87 (8) | C3B—C2B—C1B | 116.07 (8) |
C4A—C3A—C8A | 120.46 (9) | C4B—C3B—C8B | 120.32 (8) |
C4A—C3A—C2A | 118.43 (8) | C4B—C3B—C2B | 118.15 (8) |
C8A—C3A—C2A | 121.01 (8) | C8B—C3B—C2B | 121.46 (8) |
C5A—C4A—C3A | 119.73 (9) | C5B—C4B—C3B | 119.68 (9) |
C5A—C4A—H4AA | 120.1 | C5B—C4B—H4BA | 120.2 |
C3A—C4A—H4AA | 120.1 | C3B—C4B—H4BA | 120.2 |
C4A—C5A—C6A | 120.05 (9) | C4B—C5B—C6B | 120.28 (9) |
C4A—C5A—H5AA | 120.0 | C4B—C5B—H5BA | 119.9 |
C6A—C5A—H5AA | 120.0 | C6B—C5B—H5BA | 119.9 |
C7A—C6A—C5A | 120.24 (9) | C7B—C6B—C5B | 120.27 (9) |
C7A—C6A—H6AA | 119.9 | C7B—C6B—H6BA | 119.9 |
C5A—C6A—H6AA | 119.9 | C5B—C6B—H6BA | 119.9 |
C6A—C7A—C8A | 120.27 (9) | C6B—C7B—C8B | 120.06 (9) |
C6A—C7A—H7AA | 119.9 | C6B—C7B—H7BA | 120.0 |
C8A—C7A—H7AA | 119.9 | C8B—C7B—H7BA | 120.0 |
C7A—C8A—C3A | 119.21 (8) | C7B—C8B—C3B | 119.38 (8) |
C7A—C8A—C9A | 119.22 (8) | C7B—C8B—C9B | 118.89 (8) |
C3A—C8A—C9A | 121.49 (8) | C3B—C8B—C9B | 121.71 (8) |
O2A—C9A—C8A | 122.09 (8) | O2B—C9B—C8B | 122.13 (8) |
O2A—C9A—C10A | 120.53 (8) | O2B—C9B—C10B | 120.52 (8) |
C8A—C9A—C10A | 116.99 (7) | C8B—C9B—C10B | 117.01 (7) |
C11A—C10A—C9A | 109.57 (8) | C11B—C10B—C9B | 110.24 (8) |
C11A—C10A—C1A | 85.77 (7) | C11B—C10B—C1B | 85.66 (7) |
C9A—C10A—C1A | 116.59 (7) | C9B—C10B—C1B | 117.36 (7) |
C11A—C10A—Cl2A | 115.92 (7) | C11B—C10B—Cl2B | 114.97 (7) |
C9A—C10A—Cl2A | 110.30 (6) | C9B—C10B—Cl2B | 110.36 (6) |
C1A—C10A—Cl2A | 116.64 (7) | C1B—C10B—Cl2B | 116.16 (7) |
C12A—C11A—C10A | 94.88 (8) | C12B—C11B—C10B | 95.06 (8) |
C12A—C11A—H11A | 139.2 | C12B—C11B—H11B | 133.6 |
C10A—C11A—H11A | 123.9 | C10B—C11B—H11B | 131.0 |
C11A—C12A—C13A | 137.08 (9) | C11B—C12B—C13B | 136.65 (10) |
C11A—C12A—C1A | 94.17 (8) | C11B—C12B—C1B | 94.03 (8) |
C13A—C12A—C1A | 128.72 (8) | C13B—C12B—C1B | 129.30 (9) |
C18A—C13A—C14A | 119.00 (9) | C18B—C13B—C14B | 119.02 (10) |
C18A—C13A—C12A | 119.23 (9) | C18B—C13B—C12B | 119.99 (10) |
C14A—C13A—C12A | 121.72 (9) | C14B—C13B—C12B | 120.99 (10) |
C15A—C14A—C13A | 119.38 (10) | C15B—C14B—C13B | 119.45 (12) |
C15A—C14A—C19A | 118.86 (10) | C15B—C14B—C19B | 118.28 (11) |
C13A—C14A—C19A | 121.75 (9) | C13B—C14B—C19B | 122.25 (10) |
C16A—C15A—C14A | 120.89 (11) | C16B—C15B—C14B | 120.47 (13) |
C16A—C15A—H15A | 119.6 | C16B—C15B—H15B | 119.8 |
C14A—C15A—H15A | 119.6 | C14B—C15B—H15B | 119.8 |
C15A—C16A—C17A | 119.93 (11) | C15B—C16B—C17B | 120.39 (12) |
C15A—C16A—H16A | 120.0 | C15B—C16B—H16B | 119.8 |
C17A—C16A—H16A | 120.0 | C17B—C16B—H16B | 119.8 |
C16A—C17A—C18A | 119.98 (12) | C16B—C17B—C18B | 119.91 (14) |
C16A—C17A—H17A | 120.0 | C16B—C17B—H17B | 120.0 |
C18A—C17A—H17A | 120.0 | C18B—C17B—H17B | 120.0 |
C17A—C18A—C13A | 120.79 (11) | C17B—C18B—C13B | 120.74 (12) |
C17A—C18A—H18A | 119.6 | C17B—C18B—H18B | 119.6 |
C13A—C18A—H18A | 119.6 | C13B—C18B—H18B | 119.6 |
C20A—C19A—C14A | 177.43 (12) | C20B—C19B—C14B | 176.29 (13) |
C19A—C20A—H20A | 166.1 | C19B—C20B—H20B | 174.3 |
C12A—C1A—C2A—O1A | 116.09 (10) | C12B—C1B—C2B—O1B | 113.89 (11) |
C10A—C1A—C2A—O1A | −146.04 (9) | C10B—C1B—C2B—O1B | −147.77 (9) |
Cl1A—C1A—C2A—O1A | −13.47 (12) | Cl1B—C1B—C2B—O1B | −15.26 (12) |
C12A—C1A—C2A—C3A | −62.10 (11) | C12B—C1B—C2B—C3B | −64.99 (11) |
C10A—C1A—C2A—C3A | 35.77 (11) | C10B—C1B—C2B—C3B | 33.36 (11) |
Cl1A—C1A—C2A—C3A | 168.34 (7) | Cl1B—C1B—C2B—C3B | 165.86 (7) |
O1A—C2A—C3A—C4A | −26.36 (14) | O1B—C2B—C3B—C4B | −25.97 (14) |
C1A—C2A—C3A—C4A | 151.84 (9) | C1B—C2B—C3B—C4B | 152.91 (8) |
O1A—C2A—C3A—C8A | 150.14 (10) | O1B—C2B—C3B—C8B | 151.02 (10) |
C1A—C2A—C3A—C8A | −31.67 (12) | C1B—C2B—C3B—C8B | −30.10 (12) |
C8A—C3A—C4A—C5A | 1.06 (15) | C8B—C3B—C4B—C5B | 1.07 (14) |
C2A—C3A—C4A—C5A | 177.57 (9) | C2B—C3B—C4B—C5B | 178.10 (9) |
C3A—C4A—C5A—C6A | −1.82 (15) | C3B—C4B—C5B—C6B | −1.63 (15) |
C4A—C5A—C6A—C7A | 1.13 (16) | C4B—C5B—C6B—C7B | 0.90 (16) |
C5A—C6A—C7A—C8A | 0.33 (16) | C5B—C6B—C7B—C8B | 0.41 (15) |
C6A—C7A—C8A—C3A | −1.08 (15) | C6B—C7B—C8B—C3B | −0.96 (14) |
C6A—C7A—C8A—C9A | −177.76 (9) | C6B—C7B—C8B—C9B | −179.00 (9) |
C4A—C3A—C8A—C7A | 0.39 (14) | C4B—C3B—C8B—C7B | 0.22 (13) |
C2A—C3A—C8A—C7A | −176.03 (9) | C2B—C3B—C8B—C7B | −176.71 (9) |
C4A—C3A—C8A—C9A | 176.99 (9) | C4B—C3B—C8B—C9B | 178.20 (9) |
C2A—C3A—C8A—C9A | 0.57 (14) | C2B—C3B—C8B—C9B | 1.27 (14) |
C7A—C8A—C9A—O2A | 13.92 (15) | C7B—C8B—C9B—O2B | 13.62 (15) |
C3A—C8A—C9A—O2A | −162.68 (10) | C3B—C8B—C9B—O2B | −164.37 (10) |
C7A—C8A—C9A—C10A | −158.93 (9) | C7B—C8B—C9B—C10B | −159.69 (9) |
C3A—C8A—C9A—C10A | 24.47 (13) | C3B—C8B—C9B—C10B | 22.32 (13) |
O2A—C9A—C10A—C11A | −95.23 (11) | O2B—C9B—C10B—C11B | −93.93 (11) |
C8A—C9A—C10A—C11A | 77.74 (10) | C8B—C9B—C10B—C11B | 79.50 (10) |
O2A—C9A—C10A—C1A | 169.58 (9) | O2B—C9B—C10B—C1B | 170.33 (9) |
C8A—C9A—C10A—C1A | −17.45 (12) | C8B—C9B—C10B—C1B | −16.24 (12) |
O2A—C9A—C10A—Cl2A | 33.54 (12) | O2B—C9B—C10B—Cl2B | 34.15 (12) |
C8A—C9A—C10A—Cl2A | −153.50 (7) | C8B—C9B—C10B—Cl2B | −152.42 (7) |
C12A—C1A—C10A—C11A | −3.21 (7) | C2B—C1B—C10B—C11B | −121.39 (9) |
C2A—C1A—C10A—C11A | −121.49 (8) | C12B—C1B—C10B—C11B | −2.51 (7) |
Cl1A—C1A—C10A—C11A | 108.76 (7) | Cl1B—C1B—C10B—C11B | 109.28 (7) |
C12A—C1A—C10A—C9A | 106.58 (9) | C2B—C1B—C10B—C9B | −10.82 (12) |
C2A—C1A—C10A—C9A | −11.70 (12) | C12B—C1B—C10B—C9B | 108.07 (9) |
Cl1A—C1A—C10A—C9A | −141.45 (7) | Cl1B—C1B—C10B—C9B | −140.15 (7) |
C12A—C1A—C10A—Cl2A | −120.17 (7) | C2B—C1B—C10B—Cl2B | 122.87 (8) |
C2A—C1A—C10A—Cl2A | 121.55 (8) | C12B—C1B—C10B—Cl2B | −118.25 (7) |
Cl1A—C1A—C10A—Cl2A | −8.19 (10) | Cl1B—C1B—C10B—Cl2B | −6.46 (10) |
C9A—C10A—C11A—C12A | −113.12 (8) | C9B—C10B—C11B—C12B | −114.75 (8) |
C1A—C10A—C11A—C12A | 3.62 (8) | C1B—C10B—C11B—C12B | 2.85 (8) |
Cl2A—C10A—C11A—C12A | 121.27 (8) | Cl2B—C10B—C11B—C12B | 119.74 (8) |
C10A—C11A—C12A—C13A | 174.32 (12) | C10B—C11B—C12B—C13B | 178.76 (12) |
C10A—C11A—C12A—C1A | −3.79 (8) | C10B—C11B—C12B—C1B | −2.96 (8) |
C2A—C1A—C12A—C11A | 119.42 (9) | C2B—C1B—C12B—C11B | 118.85 (9) |
C10A—C1A—C12A—C11A | 3.58 (7) | C10B—C1B—C12B—C11B | 2.81 (8) |
Cl1A—C1A—C12A—C11A | −112.07 (7) | Cl1B—C1B—C12B—C11B | −113.14 (7) |
C2A—C1A—C12A—C13A | −58.93 (13) | C2B—C1B—C12B—C13B | −62.68 (13) |
C10A—C1A—C12A—C13A | −174.77 (10) | C10B—C1B—C12B—C13B | −178.72 (10) |
Cl1A—C1A—C12A—C13A | 69.58 (12) | Cl1B—C1B—C12B—C13B | 65.33 (12) |
C11A—C12A—C13A—C18A | −166.50 (13) | C11B—C12B—C13B—C18B | −162.10 (13) |
C1A—C12A—C13A—C18A | 11.08 (16) | C1B—C12B—C13B—C18B | 20.12 (16) |
C11A—C12A—C13A—C14A | 11.11 (19) | C11B—C12B—C13B—C14B | 18.36 (19) |
C1A—C12A—C13A—C14A | −171.31 (10) | C1B—C12B—C13B—C14B | −159.42 (10) |
C18A—C13A—C14A—C15A | 1.10 (16) | C18B—C13B—C14B—C15B | 0.55 (17) |
C12A—C13A—C14A—C15A | −176.52 (10) | C12B—C13B—C14B—C15B | −179.90 (11) |
C18A—C13A—C14A—C19A | 179.84 (11) | C18B—C13B—C14B—C19B | −177.46 (12) |
C12A—C13A—C14A—C19A | 2.23 (16) | C12B—C13B—C14B—C19B | 2.08 (17) |
C13A—C14A—C15A—C16A | −0.12 (18) | C13B—C14B—C15B—C16B | 0.5 (2) |
C19A—C14A—C15A—C16A | −178.91 (12) | C19B—C14B—C15B—C16B | 178.57 (13) |
C14A—C15A—C16A—C17A | −0.1 (2) | C14B—C15B—C16B—C17B | −0.5 (2) |
C15A—C16A—C17A—C18A | −0.7 (2) | C15B—C16B—C17B—C18B | −0.6 (2) |
C16A—C17A—C18A—C13A | 1.7 (2) | C16B—C17B—C18B—C13B | 1.7 (2) |
C14A—C13A—C18A—C17A | −1.91 (19) | C14B—C13B—C18B—C17B | −1.62 (18) |
C12A—C13A—C18A—C17A | 175.76 (12) | C12B—C13B—C18B—C17B | 178.83 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5A—H5AA···Cl1Ai | 0.93 | 2.78 | 3.603 (1) | 148 |
C7A—H7AA···Cl1Aii | 0.93 | 2.72 | 3.651 (1) | 177 |
C4B—H4BA···Cl2Biii | 0.93 | 2.83 | 3.715 (1) | 160 |
C5B—H5BA···Cl1Biv | 0.93 | 2.77 | 3.584 (1) | 147 |
C7B—H7BA···Cl1Bv | 0.93 | 2.75 | 3.682 (1) | 176 |
C20A—H20A···Cl1Bvi | 0.97 | 2.80 | 3.607 (1) | 142 |
C15A—H15A···Cg1vii | 0.93 | 2.55 | 3.479 (1) | 175 |
Symmetry codes: (i) x+1/2, −y+3/2, z; (ii) x+1/2, −y+1/2, z; (iii) x, y+1, z; (iv) x−1/2, −y+5/2, z; (v) x−1/2, −y+3/2, z; (vi) −x+1, −y+1, z−1/2; (vii) −x+1/2, y−1/2, z−1/2. |