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Crystals of 4-chloro-2′-biphenylol grown at 263 K and studied at both 293 and 142 K are loosely packed and contain OH
O bonded tetramers composed of four crystallographically independent molecules (Z′ = 4). Approximate symmetry relationships between independent molecules are apparent in many, perhaps even most, structures with Z′ > 1, but are not obvious in this structure. The inefficient crystal packing, the surprisingly large value of Z′ and the absence of pseudosymmetry reflect the difficulty of finding a dense molecular arrangement that also allows for hydrogen-bond formation. Impediments to good packing are the steric congestion around the ortho hydroxyl groups and the difficulty in filling space with significantly twisted biphenyl fragments. The packing arrangement adopted is strongly reminiscent of the structure type found for eight simple 4,4′-biphenyl derivatives, but one of the four independent 4-chloro-2′-biphenylol molecules has an orientation that is significantly different from the orientations of the other three and that does not fit the 4,4′-XPhPhY pattern. It is suggested that molecules that crystallize with Z′ > 1 are good candidates for solid-state compound formation.
O bonded tetramers composed of four crystallographically independent molecules (Z′ = 4). Approximate symmetry relationships between independent molecules are apparent in many, perhaps even most, structures with Z′ > 1, but are not obvious in this structure. The inefficient crystal packing, the surprisingly large value of Z′ and the absence of pseudosymmetry reflect the difficulty of finding a dense molecular arrangement that also allows for hydrogen-bond formation. Impediments to good packing are the steric congestion around the ortho hydroxyl groups and the difficulty in filling space with significantly twisted biphenyl fragments. The packing arrangement adopted is strongly reminiscent of the structure type found for eight simple 4,4′-biphenyl derivatives, but one of the four independent 4-chloro-2′-biphenylol molecules has an orientation that is significantly different from the orientations of the other three and that does not fit the 4,4′-XPhPhY pattern. It is suggested that molecules that crystallize with Z′ > 1 are good candidates for solid-state compound formation.Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768101018043/ns0006sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S0108768101018043/ns0006k00209sup2.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768101018043/ns0006k00201sup3.hkl |
CCDC references: 180219; 180220
Computing details top
For both compounds, data collection: COLLECT software (Nonius, 1999); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997). Program(s) used to solve structure: From structure at 142 K for k00209; SIR92 (Altomare, Cascarano, Giacovazzo, Guagliardi, Burla, Polidori & Camalli, 1994) in maXus (Mackay, Gilmore, Edwards, Tremayne, Stewart & Shankland, 1998) for k00201. For both compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL PC (Sheldrick, 1990).
(k00209) 4-chloro-2'-biphenylol top
Crystal data top
| C12H9ClO | Dx = 1.316 Mg m−3 |
| Mr = 204.64 | Melting point: 41-43_C K |
| Monoclinic, P121/c1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 17.418 (3) Å | Cell parameters from 33500 reflections |
| b = 12.015 (2) Å | θ = 1.0–25.0° |
| c = 19.841 (3) Å | µ = 0.33 mm−1 |
| β = 95.59 (2)° | T = 293 K |
| V = 4132.5 (12) Å3 | Pointed laths elongated along b. Crystals are thinnest in direction a*., colourless |
| Z = 16 | 0.26 × 0.25 × 0.05 mm |
| F(000) = 1696 |
Data collection top
| Nonius Kappa-CCD diffractometer | 7262 independent reflections |
| Radiation source: fine-focus sealed tube | 4186 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.028 |
| Detector resolution: 18 pixels mm-1 | θmax = 25.0°, θmin = 1.2° |
| ω scans with 1.0° steps at χ=55° | h = 0→20 |
| Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | k = 0→14 |
| Tmin = 0.92, Tmax = 0.98 | l = −23→23 |
| 9897 measured reflections |
Refinement top
| 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)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.112 | w = 1/[σ2(Fo2) + (0.04P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 1.16 | (Δ/σ)max = 0.001 |
| 7262 reflections | Δρmax = 0.30 e Å−3 |
| 510 parameters | Δρmin = −0.29 e Å−3 |
| 0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0032 (4) |
Special details top
Experimental. The crystal-to-detector distance was 36 mm. Each frame was measured for 60 s. The number of scan sets measured was 4; the total number of frames measured was 463. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| ClA | 0.85484 (5) | 0.67339 (6) | 0.65174 (4) | 0.1117 (3) | |
| OA | 0.82138 (9) | 0.14113 (12) | 0.56904 (7) | 0.0643 (4) | |
| HA | 0.8092 | 0.0895 | 0.5432 | 0.096* | |
| C1A | 0.88198 (12) | 0.30034 (19) | 0.66579 (11) | 0.0551 (6) | |
| C2A | 0.85701 (13) | 0.3622 (2) | 0.71853 (12) | 0.0679 (7) | |
| H2A | 0.8461 | 0.3258 | 0.7578 | 0.081* | |
| C3A | 0.84788 (14) | 0.4762 (2) | 0.71436 (14) | 0.0747 (7) | |
| H3A | 0.8306 | 0.5158 | 0.7502 | 0.090* | |
| C4A | 0.86455 (14) | 0.5300 (2) | 0.65682 (15) | 0.0697 (7) | |
| C5A | 0.88845 (14) | 0.4719 (2) | 0.60351 (14) | 0.0766 (7) | |
| H5A | 0.8992 | 0.5090 | 0.5644 | 0.092* | |
| C6A | 0.89667 (13) | 0.3573 (2) | 0.60800 (12) | 0.0674 (7) | |
| H6A | 0.9124 | 0.3181 | 0.5714 | 0.081* | |
| C7A | 0.89540 (12) | 0.17904 (19) | 0.67347 (12) | 0.0538 (6) | |
| C8A | 0.86755 (12) | 0.1015 (2) | 0.62479 (12) | 0.0545 (6) | |
| C9A | 0.88242 (13) | −0.0097 (2) | 0.63310 (14) | 0.0693 (7) | |
| H9A | 0.8637 | −0.0598 | 0.5997 | 0.083* | |
| C10A | 0.92506 (14) | −0.0479 (2) | 0.69077 (15) | 0.0758 (8) | |
| H10A | 0.9356 | −0.1234 | 0.6959 | 0.091* | |
| C11A | 0.95187 (13) | 0.0254 (2) | 0.74035 (14) | 0.0762 (7) | |
| H11A | 0.9796 | 0.0000 | 0.7798 | 0.091* | |
| C12A | 0.93723 (13) | 0.1377 (2) | 0.73110 (12) | 0.0654 (7) | |
| H12A | 0.9561 | 0.1873 | 0.7647 | 0.079* | |
| ClB | 0.91162 (5) | 0.40671 (5) | 0.41143 (4) | 0.1211 (4) | |
| OB | 0.75176 (8) | −0.05057 (11) | 0.49362 (8) | 0.0592 (4) | |
| HB | 0.7191 | −0.0839 | 0.5128 | 0.089* | |
| C1B | 0.86573 (14) | 0.03780 (17) | 0.41839 (10) | 0.0527 (6) | |
| C2B | 0.93952 (15) | 0.0808 (2) | 0.43334 (12) | 0.0723 (7) | |
| H2B | 0.9803 | 0.0326 | 0.4453 | 0.087* | |
| C3B | 0.95338 (16) | 0.1945 (2) | 0.43077 (13) | 0.0835 (8) | |
| H3B | 1.0028 | 0.2225 | 0.4418 | 0.100* | |
| C4B | 0.8938 (2) | 0.2645 (2) | 0.41200 (13) | 0.0749 (8) | |
| C5B | 0.82097 (17) | 0.2245 (2) | 0.39443 (12) | 0.0715 (7) | |
| H5B | 0.7810 | 0.2731 | 0.3804 | 0.086* | |
| C6B | 0.80720 (14) | 0.11175 (19) | 0.39775 (11) | 0.0593 (6) | |
| H6B | 0.7577 | 0.0849 | 0.3859 | 0.071* | |
| C7B | 0.85245 (12) | −0.08364 (17) | 0.42397 (11) | 0.0528 (6) | |
| C8B | 0.79507 (12) | −0.12604 (19) | 0.46092 (11) | 0.0512 (6) | |
| C9B | 0.78386 (14) | −0.2384 (2) | 0.46703 (12) | 0.0678 (7) | |
| H9B | 0.7456 | −0.2648 | 0.4925 | 0.081* | |
| C10B | 0.82926 (17) | −0.3120 (2) | 0.43551 (15) | 0.0858 (8) | |
| H10B | 0.8211 | −0.3882 | 0.4389 | 0.103* | |
| C11B | 0.88659 (17) | −0.2727 (2) | 0.39912 (15) | 0.0885 (8) | |
| H11B | 0.9176 | −0.3223 | 0.3781 | 0.106* | |
| C12B | 0.89826 (14) | −0.1599 (2) | 0.39370 (13) | 0.0723 (7) | |
| H12B | 0.9376 | −0.1343 | 0.3693 | 0.087* | |
| ClC | 0.71821 (4) | −0.60374 (5) | 0.49097 (4) | 0.0893 (3) | |
| OC | 0.63907 (8) | −0.09850 (10) | 0.58749 (7) | 0.0569 (4) | |
| HC | 0.6510 | −0.0381 | 0.6047 | 0.085* | |
| C1C | 0.57713 (12) | −0.30106 (17) | 0.53323 (11) | 0.0506 (6) | |
| C2C | 0.56921 (14) | −0.35276 (19) | 0.47045 (13) | 0.0724 (7) | |
| H2C | 0.5343 | −0.3241 | 0.4364 | 0.087* | |
| C3C | 0.61171 (15) | −0.4455 (2) | 0.45741 (13) | 0.0763 (8) | |
| H3C | 0.6056 | −0.4789 | 0.4149 | 0.092* | |
| C4C | 0.66295 (13) | −0.48801 (17) | 0.50730 (14) | 0.0609 (7) | |
| C5C | 0.67181 (13) | −0.43963 (18) | 0.57033 (13) | 0.0614 (6) | |
| H5C | 0.7060 | −0.4698 | 0.6044 | 0.074* | |
| C6C | 0.62954 (13) | −0.34593 (17) | 0.58265 (12) | 0.0561 (6) | |
| H6C | 0.6364 | −0.3123 | 0.6250 | 0.067* | |
| C7C | 0.52864 (13) | −0.20295 (17) | 0.54702 (10) | 0.0484 (5) | |
| C8C | 0.55993 (13) | −0.10534 (18) | 0.57536 (10) | 0.0473 (6) | |
| C9C | 0.51253 (14) | −0.01696 (17) | 0.58855 (10) | 0.0549 (6) | |
| H9C | 0.5337 | 0.0477 | 0.6082 | 0.066* | |
| C10C | 0.43371 (15) | −0.0249 (2) | 0.57243 (11) | 0.0631 (7) | |
| H10C | 0.4020 | 0.0344 | 0.5814 | 0.076* | |
| C11C | 0.40211 (14) | −0.1202 (2) | 0.54318 (12) | 0.0654 (7) | |
| H11C | 0.3492 | −0.1251 | 0.5316 | 0.079* | |
| C12C | 0.44922 (14) | −0.20761 (19) | 0.53124 (11) | 0.0603 (6) | |
| H12C | 0.4274 | −0.2722 | 0.5120 | 0.072* | |
| ClD | 0.66916 (6) | −0.35465 (6) | 0.79339 (4) | 0.1305 (4) | |
| OD | 0.69011 (9) | 0.10990 (11) | 0.63611 (8) | 0.0667 (5) | |
| HD | 0.7173 | 0.1435 | 0.6114 | 0.100* | |
| C1D | 0.64938 (15) | 0.01482 (19) | 0.75631 (11) | 0.0585 (6) | |
| C2D | 0.58515 (15) | −0.0481 (2) | 0.76658 (12) | 0.0729 (7) | |
| H2D | 0.5372 | −0.0137 | 0.7657 | 0.088* | |
| C3D | 0.59100 (19) | −0.1617 (3) | 0.77813 (13) | 0.0869 (8) | |
| H3D | 0.5474 | −0.2035 | 0.7846 | 0.104* | |
| C4D | 0.6620 (2) | −0.2113 (2) | 0.77984 (12) | 0.0817 (8) | |
| C5D | 0.72583 (19) | −0.1517 (3) | 0.76991 (14) | 0.0895 (9) | |
| H5D | 0.7736 | −0.1866 | 0.7710 | 0.107* | |
| C6D | 0.71960 (15) | −0.0398 (2) | 0.75823 (12) | 0.0758 (7) | |
| H6D | 0.7637 | 0.0008 | 0.7514 | 0.091* | |
| C7D | 0.64317 (12) | 0.13641 (19) | 0.74252 (12) | 0.0552 (6) | |
| C8D | 0.66481 (12) | 0.18256 (19) | 0.68313 (12) | 0.0540 (6) | |
| C9D | 0.65952 (13) | 0.2945 (2) | 0.66976 (13) | 0.0715 (7) | |
| H9D | 0.6743 | 0.3230 | 0.6294 | 0.086* | |
| C10D | 0.63201 (16) | 0.3643 (2) | 0.71710 (17) | 0.0881 (9) | |
| H10D | 0.6283 | 0.4403 | 0.7086 | 0.106* | |
| C11D | 0.61029 (16) | 0.3227 (2) | 0.77593 (16) | 0.0922 (9) | |
| H11D | 0.5920 | 0.3703 | 0.8077 | 0.111* | |
| C12D | 0.61524 (14) | 0.2094 (2) | 0.78875 (12) | 0.0804 (8) | |
| H12D | 0.5996 | 0.1817 | 0.8290 | 0.096* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| ClA | 0.1242 (7) | 0.0714 (5) | 0.1340 (7) | −0.0102 (4) | −0.0148 (5) | −0.0007 (4) |
| OA | 0.0635 (10) | 0.0786 (10) | 0.0501 (11) | −0.0007 (9) | 0.0015 (9) | −0.0116 (8) |
| C1A | 0.0462 (14) | 0.0723 (17) | 0.0465 (16) | −0.0076 (12) | 0.0040 (12) | −0.0029 (14) |
| C2A | 0.0715 (18) | 0.0758 (18) | 0.0576 (17) | −0.0073 (14) | 0.0122 (14) | −0.0062 (14) |
| C3A | 0.0712 (18) | 0.0787 (19) | 0.074 (2) | −0.0034 (15) | 0.0077 (15) | −0.0190 (16) |
| C4A | 0.0634 (18) | 0.0648 (17) | 0.078 (2) | −0.0094 (13) | −0.0078 (16) | −0.0036 (16) |
| C5A | 0.0778 (19) | 0.083 (2) | 0.068 (2) | −0.0172 (16) | 0.0010 (15) | 0.0104 (17) |
| C6A | 0.0680 (17) | 0.0820 (19) | 0.0524 (17) | −0.0078 (14) | 0.0072 (13) | −0.0070 (14) |
| C7A | 0.0454 (14) | 0.0712 (17) | 0.0452 (15) | −0.0006 (13) | 0.0057 (12) | −0.0035 (14) |
| C8A | 0.0419 (14) | 0.0733 (18) | 0.0488 (16) | 0.0052 (13) | 0.0072 (12) | −0.0055 (14) |
| C9A | 0.0587 (17) | 0.0761 (19) | 0.072 (2) | 0.0096 (14) | 0.0017 (15) | −0.0178 (15) |
| C10A | 0.0679 (18) | 0.0722 (18) | 0.086 (2) | 0.0123 (15) | 0.0026 (16) | −0.0088 (18) |
| C11A | 0.0609 (17) | 0.091 (2) | 0.075 (2) | 0.0110 (16) | −0.0041 (14) | 0.0041 (18) |
| C12A | 0.0603 (17) | 0.0789 (19) | 0.0561 (18) | −0.0043 (14) | 0.0005 (14) | −0.0102 (14) |
| ClB | 0.1854 (9) | 0.0639 (5) | 0.1273 (7) | −0.0200 (5) | 0.0827 (7) | −0.0062 (4) |
| OB | 0.0547 (10) | 0.0619 (9) | 0.0645 (11) | −0.0002 (8) | 0.0225 (8) | −0.0056 (8) |
| C1B | 0.0532 (16) | 0.0568 (15) | 0.0511 (15) | 0.0023 (14) | 0.0196 (12) | −0.0004 (12) |
| C2B | 0.0629 (19) | 0.0690 (18) | 0.088 (2) | 0.0046 (15) | 0.0234 (15) | 0.0087 (14) |
| C3B | 0.079 (2) | 0.084 (2) | 0.093 (2) | −0.0199 (18) | 0.0355 (17) | −0.0056 (17) |
| C4B | 0.102 (2) | 0.0597 (17) | 0.0701 (19) | −0.0024 (18) | 0.0469 (18) | −0.0027 (14) |
| C5B | 0.088 (2) | 0.0683 (19) | 0.0622 (17) | 0.0194 (16) | 0.0290 (16) | 0.0053 (14) |
| C6B | 0.0629 (16) | 0.0611 (16) | 0.0561 (16) | 0.0094 (14) | 0.0171 (13) | 0.0020 (12) |
| C7B | 0.0489 (15) | 0.0583 (15) | 0.0520 (15) | 0.0091 (13) | 0.0090 (12) | 0.0008 (12) |
| C8B | 0.0463 (14) | 0.0576 (15) | 0.0498 (15) | 0.0040 (12) | 0.0044 (12) | −0.0008 (12) |
| C9B | 0.0738 (17) | 0.0626 (17) | 0.0684 (17) | −0.0056 (14) | 0.0145 (14) | −0.0004 (14) |
| C10B | 0.099 (2) | 0.0555 (16) | 0.105 (2) | 0.0056 (16) | 0.0208 (19) | −0.0035 (16) |
| C11B | 0.094 (2) | 0.066 (2) | 0.109 (2) | 0.0221 (16) | 0.0293 (19) | −0.0125 (17) |
| C12B | 0.0691 (17) | 0.0678 (18) | 0.0840 (19) | 0.0115 (14) | 0.0272 (14) | −0.0019 (15) |
| ClC | 0.0763 (5) | 0.0640 (4) | 0.1302 (7) | 0.0049 (3) | 0.0227 (4) | −0.0253 (4) |
| OC | 0.0545 (11) | 0.0545 (9) | 0.0623 (11) | −0.0031 (7) | 0.0088 (8) | −0.0125 (8) |
| C1C | 0.0517 (14) | 0.0506 (13) | 0.0492 (15) | −0.0054 (12) | 0.0039 (12) | 0.0010 (12) |
| C2C | 0.0851 (19) | 0.0705 (17) | 0.0578 (18) | 0.0122 (15) | −0.0119 (14) | −0.0072 (14) |
| C3C | 0.091 (2) | 0.0721 (18) | 0.0640 (18) | 0.0087 (16) | −0.0019 (16) | −0.0244 (15) |
| C4C | 0.0556 (16) | 0.0489 (14) | 0.079 (2) | −0.0030 (12) | 0.0095 (15) | −0.0108 (14) |
| C5C | 0.0599 (16) | 0.0507 (14) | 0.0720 (19) | 0.0010 (12) | −0.0014 (14) | 0.0044 (14) |
| C6C | 0.0644 (16) | 0.0517 (14) | 0.0513 (15) | −0.0009 (13) | 0.0016 (13) | −0.0038 (12) |
| C7C | 0.0504 (15) | 0.0511 (14) | 0.0443 (14) | 0.0006 (12) | 0.0077 (11) | 0.0035 (11) |
| C8C | 0.0465 (15) | 0.0598 (15) | 0.0374 (13) | 0.0019 (13) | 0.0130 (11) | 0.0037 (11) |
| C9C | 0.0692 (18) | 0.0548 (14) | 0.0431 (14) | 0.0055 (13) | 0.0174 (13) | 0.0014 (11) |
| C10C | 0.0652 (19) | 0.0729 (18) | 0.0543 (16) | 0.0227 (15) | 0.0221 (14) | 0.0101 (14) |
| C11C | 0.0523 (16) | 0.0809 (18) | 0.0639 (17) | 0.0053 (16) | 0.0097 (13) | 0.0099 (15) |
| C12C | 0.0572 (17) | 0.0604 (15) | 0.0634 (16) | −0.0056 (14) | 0.0058 (13) | 0.0032 (13) |
| ClD | 0.2051 (10) | 0.0741 (5) | 0.1082 (7) | 0.0049 (5) | −0.0065 (7) | 0.0164 (5) |
| OD | 0.0771 (12) | 0.0584 (10) | 0.0691 (12) | −0.0090 (8) | 0.0298 (9) | −0.0139 (9) |
| C1D | 0.0616 (18) | 0.0692 (17) | 0.0444 (15) | 0.0056 (15) | 0.0035 (13) | −0.0029 (12) |
| C2D | 0.0704 (19) | 0.083 (2) | 0.0659 (18) | 0.0005 (16) | 0.0115 (14) | 0.0042 (15) |
| C3D | 0.102 (3) | 0.087 (2) | 0.071 (2) | −0.0230 (19) | 0.0069 (17) | 0.0121 (16) |
| C4D | 0.119 (3) | 0.0660 (18) | 0.0576 (17) | 0.002 (2) | −0.0048 (18) | 0.0049 (14) |
| C5D | 0.098 (3) | 0.078 (2) | 0.091 (2) | 0.0205 (19) | −0.0011 (18) | 0.0069 (17) |
| C6D | 0.073 (2) | 0.0752 (19) | 0.079 (2) | 0.0048 (16) | 0.0056 (15) | 0.0021 (15) |
| C7D | 0.0504 (15) | 0.0652 (16) | 0.0497 (16) | 0.0042 (12) | 0.0031 (12) | −0.0118 (13) |
| C8D | 0.0477 (14) | 0.0552 (15) | 0.0601 (17) | −0.0033 (12) | 0.0107 (12) | −0.0172 (13) |
| C9D | 0.0801 (18) | 0.0553 (16) | 0.0805 (19) | −0.0061 (14) | 0.0156 (15) | −0.0088 (15) |
| C10D | 0.101 (2) | 0.0601 (17) | 0.103 (3) | 0.0088 (15) | 0.007 (2) | −0.0225 (18) |
| C11D | 0.116 (3) | 0.083 (2) | 0.077 (2) | 0.0252 (18) | 0.0096 (19) | −0.0338 (17) |
| C12D | 0.092 (2) | 0.093 (2) | 0.0574 (17) | 0.0155 (17) | 0.0140 (15) | −0.0129 (16) |
Geometric parameters (Å, º) top
| ClA—C4A | 1.733 (2) | C9A—C10A | 1.381 (3) |
| ClB—C4B | 1.737 (2) | C9B—C10B | 1.377 (3) |
| ClC—C4C | 1.739 (2) | C9C—C10C | 1.382 (3) |
| ClD—C4D | 1.746 (3) | C9D—C10D | 1.379 (3) |
| OA—C8A | 1.387 (2) | C10A—C11A | 1.368 (3) |
| OB—C8B | 1.381 (2) | C10B—C11B | 1.372 (3) |
| OC—C8C | 1.378 (2) | C10C—C11C | 1.374 (3) |
| OD—C8D | 1.381 (2) | C10D—C11D | 1.357 (4) |
| C1A—C2A | 1.387 (3) | C11A—C12A | 1.382 (3) |
| C1B—C2B | 1.390 (3) | C11B—C12B | 1.375 (3) |
| C1C—C2C | 1.387 (3) | C11C—C12C | 1.368 (3) |
| C1D—C2D | 1.382 (3) | C11D—C12D | 1.386 (3) |
| C1A—C6A | 1.381 (3) | OA—HA | 0.82 |
| C1B—C6B | 1.384 (3) | OB—HB | 0.82 |
| C1C—C6C | 1.382 (3) | OC—HC | 0.82 |
| C1D—C6D | 1.385 (3) | OD—HD | 0.82 |
| C1A—C7A | 1.481 (3) | C2A—H2A | 0.93 |
| C1B—C7B | 1.483 (3) | C2B—H2B | 0.93 |
| C1C—C7C | 1.491 (3) | C2C—H2C | 0.93 |
| C1D—C7D | 1.488 (3) | C2D—H2D | 0.93 |
| C2A—C3A | 1.380 (3) | C3A—H3A | 0.93 |
| C2B—C3B | 1.389 (3) | C3B—H3B | 0.93 |
| C2C—C3C | 1.376 (3) | C3C—H3C | 0.93 |
| C2D—C3D | 1.386 (3) | C3D—H3D | 0.93 |
| C3A—C4A | 1.368 (3) | C5A—H5A | 0.93 |
| C3B—C4B | 1.359 (3) | C5B—H5B | 0.93 |
| C3C—C4C | 1.366 (3) | C5C—H5C | 0.93 |
| C3D—C4D | 1.370 (4) | C5D—H5D | 0.93 |
| C4A—C5A | 1.366 (3) | C6A—H6A | 0.93 |
| C4B—C5B | 1.369 (3) | C6B—H6B | 0.93 |
| C4C—C5C | 1.374 (3) | C6C—H6C | 0.93 |
| C4D—C5D | 1.354 (4) | C6D—H6D | 0.93 |
| C5A—C6A | 1.386 (3) | C9A—H9A | 0.93 |
| C5B—C6B | 1.378 (3) | C9B—H9B | 0.93 |
| C5C—C6C | 1.380 (3) | C9C—H9C | 0.93 |
| C5D—C6D | 1.367 (3) | C9D—H9D | 0.93 |
| C7A—C8A | 1.395 (3) | C10A—H10A | 0.93 |
| C7B—C8B | 1.392 (3) | C10B—H10B | 0.93 |
| C7C—C8C | 1.389 (3) | C10C—H10C | 0.93 |
| C7D—C8D | 1.387 (3) | C10D—H10D | 0.93 |
| C7A—C12A | 1.387 (3) | C11A—H11A | 0.93 |
| C7B—C12B | 1.390 (3) | C11B—H11B | 0.93 |
| C7C—C12C | 1.390 (3) | C11C—H11C | 0.93 |
| C7D—C12D | 1.391 (3) | C11D—H11D | 0.93 |
| C8A—C9A | 1.368 (3) | C12A—H12A | 0.93 |
| C8B—C9B | 1.371 (3) | C12B—H12B | 0.93 |
| C8C—C9C | 1.386 (3) | C12C—H12C | 0.93 |
| C8D—C9D | 1.373 (3) | C12D—H12D | 0.93 |
| C2A—C1A—C6A | 117.2 (2) | C10C—C11C—C12C | 119.4 (2) |
| C2B—C1B—C6B | 117.6 (2) | C10D—C11D—C12D | 120.1 (2) |
| C2C—C1C—C6C | 117.6 (2) | C7A—C12A—C11A | 122.3 (2) |
| C2D—C1D—C6D | 117.5 (2) | C7B—C12B—C11B | 121.4 (2) |
| C2A—C1A—C7A | 120.5 (2) | C7C—C12C—C11C | 122.1 (2) |
| C2B—C1B—C7B | 119.8 (2) | C7D—C12D—C11D | 121.2 (3) |
| C2C—C1C—C7C | 120.7 (2) | C8A—OA—HA | 109.5 |
| C2D—C1D—C7D | 121.3 (2) | C8B—OB—HB | 109.5 |
| C6A—C1A—C7A | 122.2 (2) | C8C—OC—HC | 109.5 |
| C6B—C1B—C7B | 122.5 (2) | C8D—OD—HD | 109.5 |
| C6C—C1C—C7C | 121.7 (2) | C1A—C2A—H2A | 119.0 |
| C6D—C1D—C7D | 121.2 (2) | C1B—C2B—H2B | 119.4 |
| C1A—C2A—C3A | 121.9 (2) | C1C—C2C—H2C | 119.2 |
| C1B—C2B—C3B | 121.2 (2) | C1D—C2D—H2D | 119.5 |
| C1C—C2C—C3C | 121.6 (2) | C3A—C2A—H2A | 119.0 |
| C1D—C2D—C3D | 121.1 (2) | C3B—C2B—H2B | 119.4 |
| C2A—C3A—C4A | 119.1 (2) | C3C—C2C—H2C | 119.2 |
| C2B—C3B—C4B | 119.2 (2) | C3D—C2D—H2D | 119.5 |
| C2C—C3C—C4C | 119.5 (2) | C2A—C3A—H3A | 120.4 |
| C2D—C3D—C4D | 119.0 (3) | C2B—C3B—H3B | 120.4 |
| C3A—C4A—C5A | 120.6 (2) | C2C—C3C—H3C | 120.3 |
| C3B—C4B—C5B | 121.1 (2) | C2D—C3D—H3D | 120.5 |
| C3C—C4C—C5C | 120.6 (2) | C4A—C3A—H3A | 120.4 |
| C3D—C4D—C5D | 121.2 (3) | C4B—C3B—H3B | 120.4 |
| C3A—C4A—ClA | 119.4 (2) | C4C—C3C—H3C | 120.3 |
| C3B—C4B—ClB | 118.5 (3) | C4D—C3D—H3D | 120.5 |
| C3C—C4C—ClC | 119.9 (2) | C4A—C5A—H5A | 120.1 |
| C3D—C4D—ClD | 119.0 (3) | C4B—C5B—H5B | 120.2 |
| C5A—C4A—ClA | 119.9 (2) | C4C—C5C—H5C | 120.3 |
| C5B—C4B—ClB | 120.3 (2) | C4D—C5D—H5D | 120.2 |
| C5C—C4C—ClC | 119.5 (2) | C6A—C5A—H5A | 120.1 |
| C5D—C4D—ClD | 119.8 (3) | C6B—C5B—H5B | 120.2 |
| C4A—C5A—C6A | 119.7 (2) | C6C—C5C—H5C | 120.3 |
| C4B—C5B—C6B | 119.6 (2) | C6D—C5D—H5D | 120.2 |
| C4C—C5C—C6C | 119.5 (2) | C1A—C6A—H6A | 119.3 |
| C4D—C5D—C6D | 119.5 (3) | C1B—C6B—H6B | 119.4 |
| C1A—C6A—C5A | 121.3 (2) | C1C—C6C—H6C | 119.4 |
| C1B—C6B—C5B | 121.2 (2) | C1D—C6D—H6D | 119.1 |
| C1C—C6C—C5C | 121.3 (2) | C5A—C6A—H6A | 119.3 |
| C1D—C6D—C5D | 121.7 (3) | C5B—C6B—H6B | 119.4 |
| C1A—C7A—C8A | 123.0 (2) | C5C—C6C—H6C | 119.4 |
| C1B—C7B—C8B | 121.6 (2) | C5D—C6D—H6D | 119.1 |
| C1C—C7C—C8C | 122.3 (2) | C10A—C9A—H9A | 119.8 |
| C1D—C7D—C8D | 121.8 (2) | C10B—C9B—H9B | 120.0 |
| C1A—C7A—C12A | 120.1 (2) | C10C—C9C—H9C | 120.0 |
| C1B—C7B—C12B | 121.1 (2) | C10D—C9D—H9D | 120.5 |
| C1C—C7C—C12C | 119.7 (2) | C8A—C9A—H9A | 119.8 |
| C1D—C7D—C12D | 121.4 (2) | C8B—C9B—H9B | 120.0 |
| C8A—C7A—C12A | 116.8 (2) | C8C—C9C—H9C | 120.0 |
| C8B—C7B—C12B | 117.3 (2) | C8D—C9D—H9D | 120.5 |
| C8C—C7C—C12C | 117.9 (2) | C9A—C10A—H10A | 120.0 |
| C8D—C7D—C12D | 116.7 (2) | C9B—C10B—H10B | 120.1 |
| C7A—C8A—C9A | 121.3 (2) | C9C—C10C—H10C | 119.9 |
| C7B—C8B—C9B | 121.5 (2) | C9D—C10D—H10D | 119.8 |
| C7C—C8C—C9C | 120.4 (2) | C11A—C10A—H10A | 120.0 |
| C7D—C8D—C9D | 122.5 (2) | C11B—C10B—H10B | 120.1 |
| OA—C8A—C7A | 117.3 (2) | C11C—C10C—H10C | 119.9 |
| OB—C8B—C7B | 117.39 (19) | C11D—C10D—H10D | 119.8 |
| OC—C8C—C7C | 117.86 (19) | C10A—C11A—H11A | 120.4 |
| OD—C8D—C7D | 116.9 (2) | C10B—C11B—H11B | 120.0 |
| OA—C8A—C9A | 121.3 (2) | C10C—C11C—H11C | 120.3 |
| OB—C8B—C9B | 121.1 (2) | C10D—C11D—H11D | 119.9 |
| OC—C8C—C9C | 121.7 (2) | C12A—C11A—H11A | 120.4 |
| OD—C8D—C9D | 120.6 (2) | C12B—C11B—H11B | 120.0 |
| C8A—C9A—C10A | 120.3 (2) | C12C—C11C—H11C | 120.3 |
| C8B—C9B—C10B | 120.0 (2) | C12D—C11D—H11D | 119.9 |
| C8C—C9C—C10C | 120.0 (2) | C7A—C12A—H12A | 118.8 |
| C8D—C9D—C10D | 119.0 (2) | C7B—C12B—H12B | 119.3 |
| C9A—C10A—C11A | 120.0 (2) | C7C—C12C—H12C | 119.0 |
| C9B—C10B—C11B | 119.8 (2) | C7D—C12D—H12D | 119.4 |
| C9C—C10C—C11C | 120.2 (2) | C11A—C12A—H12A | 118.8 |
| C9D—C10D—C11D | 120.4 (2) | C11B—C12B—H12B | 119.3 |
| C10A—C11A—C12A | 119.2 (2) | C11C—C12C—H12C | 119.0 |
| C10B—C11B—C12B | 120.1 (2) | C11D—C12D—H12D | 119.4 |
| C6A—C1A—C2A—C3A | −0.7 (3) | ClC—C4C—C5C—C6C | 178.16 (16) |
| C6B—C1B—C2B—C3B | 3.0 (3) | ClD—C4D—C5D—C6D | 178.93 (19) |
| C6C—C1C—C2C—C3C | 0.1 (3) | C4A—C5A—C6A—C1A | −0.7 (4) |
| C6D—C1D—C2D—C3D | −0.2 (3) | C4B—C5B—C6B—C1B | −0.1 (3) |
| C7A—C1A—C2A—C3A | 176.5 (2) | C4C—C5C—C6C—C1C | 1.4 (3) |
| C7B—C1B—C2B—C3B | −177.8 (2) | C4D—C5D—C6D—C1D | 0.1 (4) |
| C7C—C1C—C2C—C3C | −178.0 (2) | C1A—C7A—C8A—C9A | 178.7 (2) |
| C7D—C1D—C2D—C3D | 178.8 (2) | C1B—C7B—C8B—C9B | −178.8 (2) |
| C2A—C1A—C6A—C5A | 1.4 (3) | C1C—C7C—C8C—C9C | −178.72 (18) |
| C2B—C1B—C6B—C5B | −2.3 (3) | C1D—C7D—C8D—C9D | −179.9 (2) |
| C2C—C1C—C6C—C5C | −0.8 (3) | C1A—C7A—C8A—OA | −4.0 (3) |
| C2D—C1D—C6D—C5D | −0.1 (3) | C1B—C7B—C8B—OB | −1.4 (3) |
| C7A—C1A—C6A—C5A | −175.8 (2) | C1C—C7C—C8C—OC | 3.5 (3) |
| C7B—C1B—C6B—C5B | 178.60 (19) | C1D—C7D—C8D—OD | 2.1 (3) |
| C7C—C1C—C6C—C5C | 177.19 (19) | C12A—C7A—C8A—C9A | −1.4 (3) |
| C7D—C1D—C6D—C5D | −179.1 (2) | C12B—C7B—C8B—C9B | −0.3 (3) |
| C2A—C1A—C7A—C8A | 132.7 (2) | C12C—C7C—C8C—C9C | 1.4 (3) |
| C2B—C1B—C7B—C8B | 128.4 (2) | C12D—C7D—C8D—C9D | 0.1 (3) |
| C2C—C1C—C7C—C8C | −130.3 (2) | C12A—C7A—C8A—OA | 175.87 (18) |
| C2D—C1D—C7D—C8D | −119.8 (2) | C12B—C7B—C8B—OB | 177.12 (19) |
| C2A—C1A—C7A—C12A | −47.2 (3) | C12C—C7C—C8C—OC | −176.45 (17) |
| C2B—C1B—C7B—C12B | −50.0 (3) | C12D—C7D—C8D—OD | −177.87 (19) |
| C2C—C1C—C7C—C12C | 49.6 (3) | C1A—C7A—C12A—C11A | −179.4 (2) |
| C2D—C1D—C7D—C12D | 60.1 (3) | C1B—C7B—C12B—C11B | 179.5 (2) |
| C6A—C1A—C7A—C8A | −50.2 (3) | C1C—C7C—C12C—C11C | 179.7 (2) |
| C6B—C1B—C7B—C8B | −52.5 (3) | C1D—C7D—C12D—C11D | 179.4 (2) |
| C6C—C1C—C7C—C8C | 51.8 (3) | C8A—C7A—C12A—C11A | 0.7 (3) |
| C6D—C1D—C7D—C8D | 59.1 (3) | C8B—C7B—C12B—C11B | 1.0 (4) |
| C6A—C1A—C7A—C12A | 129.9 (2) | C8C—C7C—C12C—C11C | −0.4 (3) |
| C6B—C1B—C7B—C12B | 129.1 (2) | C8D—C7D—C12D—C11D | −0.7 (4) |
| C6C—C1C—C7C—C12C | −128.3 (2) | C7A—C8A—C9A—C10A | 0.7 (3) |
| C6D—C1D—C7D—C12D | −120.9 (3) | C7B—C8B—C9B—C10B | −0.8 (3) |
| C1A—C2A—C3A—C4A | −0.6 (4) | C7C—C8C—C9C—C10C | −1.1 (3) |
| C1B—C2B—C3B—C4B | −1.3 (4) | C7D—C8D—C9D—C10D | 0.3 (4) |
| C1C—C2C—C3C—C4C | 0.1 (4) | OA—C8A—C9A—C10A | −176.5 (2) |
| C1D—C2D—C3D—C4D | 0.5 (4) | OB—C8B—C9B—C10B | −178.1 (2) |
| C2A—C3A—C4A—C5A | 1.3 (4) | OC—C8C—C9C—C10C | 176.63 (19) |
| C2B—C3B—C4B—C5B | −1.3 (4) | OD—C8D—C9D—C10D | 178.2 (2) |
| C2C—C3C—C4C—C5C | 0.6 (4) | C8A—C9A—C10A—C11A | 0.8 (4) |
| C2D—C3D—C4D—C5D | −0.6 (4) | C8B—C9B—C10B—C11B | 1.2 (4) |
| C2A—C3A—C4A—ClA | −178.89 (18) | C8C—C9C—C10C—C11C | −0.2 (3) |
| C2B—C3B—C4B—ClB | 178.16 (18) | C8D—C9D—C10D—C11D | −0.2 (4) |
| C2C—C3C—C4C—ClC | −178.90 (19) | C9A—C10A—C11A—C12A | −1.5 (4) |
| C2D—C3D—C4D—ClD | −179.24 (19) | C9B—C10B—C11B—C12B | −0.5 (4) |
| C3A—C4A—C5A—C6A | −0.7 (4) | C9C—C10C—C11C—C12C | 1.1 (3) |
| C3B—C4B—C5B—C6B | 2.0 (4) | C9D—C10D—C11D—C12D | −0.3 (4) |
| C3C—C4C—C5C—C6C | −1.3 (3) | C10A—C11A—C12A—C7A | 0.8 (4) |
| C3D—C4D—C5D—C6D | 0.3 (4) | C10B—C11B—C12B—C7B | −0.6 (4) |
| ClA—C4A—C5A—C6A | 179.53 (17) | C10C—C11C—C12C—C7C | −0.8 (3) |
| ClB—C4B—C5B—C6B | −177.44 (16) | C10D—C11D—C12D—C7D | 0.8 (4) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| OA—HA···OB | 0.82 | 2.15 | 2.943 (2) | 164 (4) |
| OB—HB···OC | 0.82 | 2.14 | 2.892 (2) | 153 (4) |
| OC—HC···OD | 0.82 | 1.98 | 2.797 (2) | 172 (4) |
| OD—HD···OA | 0.82 | 2.07 | 2.781 (2) | 144 (4) |
(k00201) 4-chloro-2'-biphenylol top
Crystal data top
| C12H9ClO | Dx = 1.353 Mg m−3 |
| Mr = 204.64 | Melting point: 41-43_C K |
| Monoclinic, P121/c1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 17.211 (3) Å | Cell parameters from 20387 reflections |
| b = 11.962 (2) Å | θ = 1.0–25.0° |
| c = 19.621 (3) Å | µ = 0.34 mm−1 |
| β = 95.95 (2)° | T = 142 K |
| V = 4017.8 (11) Å3 | Pointed laths elongated along b. Crystals are thinnest in direction a*., colourless |
| Z = 16 | 0.41 × 0.25 × 0.05 mm |
| F(000) = 1696 |
Data collection top
| Nonius Kappa-CCD diffractometer | 7080 independent reflections |
| Radiation source: fine-focus sealed tube | 4349 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.052 |
| Detector resolution: 18 pixels mm-1 | θmax = 25.0°, θmin = 1.2° |
| ω scans with 2.0° steps at χ=55° | h = −20→20 |
| Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | k = −14→11 |
| Tmin = 0.87, Tmax = 0.98 | l = −23→23 |
| 11717 measured reflections |
Refinement top
| 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)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.080 | w = 1/[σ2(Fo2) + (0.02P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 0.99 | (Δ/σ)max = 0.001 |
| 7080 reflections | Δρmax = 0.33 e Å−3 |
| 522 parameters | Δρmin = −0.26 e Å−3 |
| 0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00049 (9) |
Special details top
Experimental. The crystal-to-detector distance was 45 mm. Each frame was measured for 40 s. The number of scan sets measured was 4; the total number of frames measured was 256. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| ClA | 0.85485 (4) | 0.67701 (6) | 0.65086 (3) | 0.0506 (2) | |
| OA | 0.82192 (9) | 0.14121 (15) | 0.56739 (8) | 0.0298 (5) | |
| HA | 0.8098 (13) | 0.0886 (18) | 0.5419 (11) | 0.043 (9)* | |
| C1A | 0.88220 (12) | 0.3009 (2) | 0.66576 (11) | 0.0263 (6) | |
| C2A | 0.85684 (12) | 0.3636 (2) | 0.71924 (12) | 0.0312 (6) | |
| H2A | 0.8454 | 0.3262 | 0.7597 | 0.037* | |
| C3A | 0.84789 (12) | 0.4786 (2) | 0.71514 (12) | 0.0333 (6) | |
| H3A | 0.8307 | 0.5196 | 0.7522 | 0.040* | |
| C4A | 0.86444 (12) | 0.5320 (2) | 0.65635 (13) | 0.0317 (6) | |
| C5A | 0.88895 (12) | 0.4734 (2) | 0.60218 (12) | 0.0334 (7) | |
| H5A | 0.9000 | 0.5116 | 0.5619 | 0.040* | |
| C6A | 0.89746 (12) | 0.3586 (2) | 0.60664 (11) | 0.0330 (7) | |
| H6A | 0.9139 | 0.3183 | 0.5690 | 0.040* | |
| C7A | 0.89580 (12) | 0.1793 (2) | 0.67404 (11) | 0.0261 (6) | |
| C8A | 0.86839 (12) | 0.1007 (2) | 0.62469 (11) | 0.0252 (6) | |
| C9A | 0.88308 (12) | −0.0115 (2) | 0.63300 (12) | 0.0318 (6) | |
| H9A | 0.8639 | −0.0629 | 0.5984 | 0.038* | |
| C10A | 0.92588 (13) | −0.0493 (2) | 0.69203 (12) | 0.0332 (6) | |
| H10A | 0.9371 | −0.1268 | 0.6976 | 0.040* | |
| C11A | 0.95252 (12) | 0.0258 (2) | 0.74321 (12) | 0.0326 (6) | |
| H11A | 0.9807 | 0.0001 | 0.7844 | 0.039* | |
| C12A | 0.93760 (12) | 0.1379 (2) | 0.73340 (11) | 0.0303 (6) | |
| H12A | 0.9564 | 0.1890 | 0.7683 | 0.036* | |
| ClB | 0.91269 (4) | 0.40903 (5) | 0.41272 (3) | 0.0552 (2) | |
| OB | 0.75170 (9) | −0.04981 (13) | 0.49380 (8) | 0.0280 (4) | |
| HB | 0.7189 (11) | −0.0815 (17) | 0.5131 (10) | 0.027 (8)* | |
| C1B | 0.86689 (13) | 0.03693 (19) | 0.41734 (10) | 0.0252 (6) | |
| C2B | 0.94130 (13) | 0.0806 (2) | 0.43262 (11) | 0.0340 (7) | |
| H2B | 0.9835 | 0.0308 | 0.4447 | 0.041* | |
| C3B | 0.95622 (14) | 0.1939 (2) | 0.43090 (11) | 0.0380 (7) | |
| H3B | 1.0077 | 0.2218 | 0.4421 | 0.046* | |
| C4B | 0.89518 (16) | 0.2658 (2) | 0.41260 (11) | 0.0353 (7) | |
| C5B | 0.82057 (14) | 0.2258 (2) | 0.39382 (11) | 0.0322 (6) | |
| H5B | 0.7793 | 0.2758 | 0.3791 | 0.039* | |
| C6B | 0.80673 (13) | 0.1121 (2) | 0.39670 (10) | 0.0272 (6) | |
| H6B | 0.7554 | 0.0845 | 0.3844 | 0.033* | |
| C7B | 0.85300 (12) | −0.08488 (19) | 0.42319 (11) | 0.0249 (6) | |
| C8B | 0.79486 (12) | −0.1267 (2) | 0.46116 (11) | 0.0239 (6) | |
| C9B | 0.78249 (13) | −0.2404 (2) | 0.46716 (11) | 0.0310 (6) | |
| H9B | 0.7422 | −0.2670 | 0.4926 | 0.037* | |
| C10B | 0.82888 (14) | −0.3150 (2) | 0.43607 (12) | 0.0379 (7) | |
| H10B | 0.8206 | −0.3931 | 0.4401 | 0.045* | |
| C11B | 0.88765 (14) | −0.2758 (2) | 0.39894 (12) | 0.0406 (7) | |
| H11B | 0.9198 | −0.3271 | 0.3778 | 0.049* | |
| C12B | 0.89921 (13) | −0.1628 (2) | 0.39282 (12) | 0.0345 (7) | |
| H12B | 0.9396 | −0.1369 | 0.3673 | 0.041* | |
| ClC | 0.71975 (3) | −0.60592 (5) | 0.49132 (3) | 0.0413 (2) | |
| OC | 0.64090 (9) | −0.09731 (15) | 0.58858 (8) | 0.0276 (4) | |
| HC | 0.6545 (13) | −0.0408 (17) | 0.6065 (11) | 0.033 (9)* | |
| C1C | 0.57711 (12) | −0.30037 (19) | 0.53329 (11) | 0.0233 (6) | |
| C2C | 0.56888 (13) | −0.35242 (19) | 0.46974 (12) | 0.0334 (7) | |
| H2C | 0.5329 | −0.3226 | 0.4344 | 0.040* | |
| C3C | 0.61162 (14) | −0.4466 (2) | 0.45648 (12) | 0.0369 (7) | |
| H3C | 0.6052 | −0.4812 | 0.4127 | 0.044* | |
| C4C | 0.66364 (12) | −0.48920 (18) | 0.50806 (12) | 0.0293 (6) | |
| C5C | 0.67342 (12) | −0.44015 (19) | 0.57197 (11) | 0.0275 (6) | |
| H5C | 0.7092 | −0.4707 | 0.6072 | 0.033* | |
| C6C | 0.63046 (12) | −0.34599 (18) | 0.58404 (11) | 0.0251 (6) | |
| H6C | 0.6374 | −0.3116 | 0.6279 | 0.030* | |
| C7C | 0.52898 (13) | −0.20204 (19) | 0.54693 (10) | 0.0229 (6) | |
| C8C | 0.56037 (13) | −0.1033 (2) | 0.57603 (10) | 0.0222 (6) | |
| C9C | 0.51281 (13) | −0.01386 (19) | 0.58912 (10) | 0.0256 (6) | |
| H9C | 0.5351 | 0.0523 | 0.6096 | 0.031* | |
| C10C | 0.43317 (13) | −0.0209 (2) | 0.57245 (10) | 0.0284 (6) | |
| H10C | 0.4007 | 0.0404 | 0.5814 | 0.034* | |
| C11C | 0.40040 (13) | −0.1174 (2) | 0.54274 (11) | 0.0299 (6) | |
| H11C | 0.3456 | −0.1223 | 0.5309 | 0.036* | |
| C12C | 0.44825 (13) | −0.20594 (19) | 0.53058 (10) | 0.0276 (6) | |
| H12C | 0.4254 | −0.2719 | 0.5104 | 0.033* | |
| ClD | 0.67308 (4) | −0.35580 (5) | 0.79278 (3) | 0.0580 (2) | |
| OD | 0.69079 (9) | 0.11209 (13) | 0.63502 (8) | 0.0318 (5) | |
| HD | 0.7205 (14) | 0.143 (2) | 0.6094 (13) | 0.074 (11)* | |
| C1D | 0.65087 (13) | 0.0162 (2) | 0.75648 (10) | 0.0267 (6) | |
| C2D | 0.58603 (14) | −0.0478 (2) | 0.76689 (11) | 0.0336 (6) | |
| H2D | 0.5364 | −0.0130 | 0.7662 | 0.040* | |
| C3D | 0.59268 (15) | −0.1623 (2) | 0.77826 (11) | 0.0373 (7) | |
| H3D | 0.5479 | −0.2058 | 0.7850 | 0.045* | |
| C4D | 0.66480 (17) | −0.2115 (2) | 0.77959 (11) | 0.0372 (7) | |
| C5D | 0.73011 (15) | −0.1504 (2) | 0.76963 (11) | 0.0402 (7) | |
| H5D | 0.7796 | −0.1857 | 0.7706 | 0.048* | |
| C6D | 0.72290 (14) | −0.0369 (2) | 0.75820 (11) | 0.0347 (7) | |
| H6D | 0.7680 | 0.0057 | 0.7514 | 0.042* | |
| C7D | 0.64328 (12) | 0.1384 (2) | 0.74268 (12) | 0.0260 (6) | |
| C8D | 0.66476 (12) | 0.1853 (2) | 0.68252 (12) | 0.0254 (6) | |
| C9D | 0.65814 (12) | 0.2975 (2) | 0.66855 (12) | 0.0319 (6) | |
| H9D | 0.6729 | 0.3264 | 0.6267 | 0.038* | |
| C10D | 0.62981 (13) | 0.3681 (2) | 0.71600 (13) | 0.0387 (7) | |
| H10D | 0.6253 | 0.4460 | 0.7070 | 0.046* | |
| C11D | 0.60807 (14) | 0.3253 (2) | 0.77646 (13) | 0.0424 (7) | |
| H11D | 0.5889 | 0.3737 | 0.8092 | 0.051* | |
| C12D | 0.61423 (13) | 0.2116 (2) | 0.78936 (12) | 0.0396 (7) | |
| H12D | 0.5983 | 0.1828 | 0.8309 | 0.048* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| ClA | 0.0562 (5) | 0.0354 (4) | 0.0576 (5) | −0.0049 (4) | −0.0064 (4) | 0.0021 (4) |
| OA | 0.0311 (11) | 0.0363 (12) | 0.0214 (10) | −0.0011 (9) | 0.0002 (8) | −0.0075 (10) |
| C1A | 0.0203 (14) | 0.0372 (17) | 0.0209 (15) | −0.0027 (12) | −0.0004 (11) | −0.0048 (14) |
| C2A | 0.0307 (15) | 0.0381 (17) | 0.0251 (15) | −0.0053 (13) | 0.0045 (12) | 0.0000 (14) |
| C3A | 0.0305 (16) | 0.0399 (18) | 0.0294 (16) | −0.0027 (13) | 0.0023 (12) | −0.0059 (15) |
| C4A | 0.0247 (15) | 0.0316 (16) | 0.0369 (17) | −0.0082 (12) | −0.0062 (13) | 0.0009 (14) |
| C5A | 0.0281 (15) | 0.0459 (19) | 0.0253 (16) | −0.0088 (14) | −0.0013 (12) | 0.0059 (15) |
| C6A | 0.0293 (15) | 0.0457 (19) | 0.0241 (16) | −0.0049 (13) | 0.0035 (12) | −0.0049 (14) |
| C7A | 0.0198 (14) | 0.0374 (17) | 0.0219 (15) | −0.0016 (12) | 0.0060 (12) | −0.0035 (14) |
| C8A | 0.0175 (14) | 0.0373 (17) | 0.0208 (15) | 0.0030 (13) | 0.0017 (11) | −0.0011 (14) |
| C9A | 0.0256 (15) | 0.0390 (18) | 0.0301 (16) | 0.0029 (13) | −0.0006 (12) | −0.0081 (14) |
| C10A | 0.0276 (15) | 0.0319 (17) | 0.0398 (17) | 0.0072 (13) | 0.0025 (13) | −0.0028 (14) |
| C11A | 0.0254 (15) | 0.0417 (18) | 0.0298 (16) | 0.0024 (13) | −0.0017 (12) | −0.0018 (15) |
| C12A | 0.0257 (15) | 0.0398 (18) | 0.0251 (15) | −0.0014 (13) | 0.0009 (12) | −0.0043 (14) |
| ClB | 0.0831 (6) | 0.0322 (4) | 0.0563 (5) | −0.0090 (4) | 0.0354 (4) | −0.0019 (4) |
| OB | 0.0245 (10) | 0.0314 (11) | 0.0298 (10) | −0.0023 (9) | 0.0111 (8) | −0.0008 (9) |
| C1B | 0.0245 (15) | 0.0313 (16) | 0.0212 (14) | 0.0023 (13) | 0.0093 (11) | 0.0004 (12) |
| C2B | 0.0276 (16) | 0.0394 (18) | 0.0362 (16) | 0.0040 (13) | 0.0095 (12) | 0.0030 (14) |
| C3B | 0.0324 (16) | 0.0402 (19) | 0.0441 (17) | −0.0101 (15) | 0.0166 (13) | −0.0041 (15) |
| C4B | 0.0508 (18) | 0.0293 (17) | 0.0296 (16) | −0.0032 (15) | 0.0220 (14) | −0.0019 (13) |
| C5B | 0.0448 (18) | 0.0291 (17) | 0.0245 (15) | 0.0088 (14) | 0.0119 (13) | 0.0028 (13) |
| C6B | 0.0268 (15) | 0.0351 (17) | 0.0210 (14) | 0.0049 (13) | 0.0080 (11) | −0.0004 (13) |
| C7B | 0.0204 (14) | 0.0307 (16) | 0.0231 (14) | 0.0022 (12) | −0.0005 (11) | −0.0003 (13) |
| C8B | 0.0239 (14) | 0.0285 (16) | 0.0188 (14) | 0.0050 (13) | 0.0005 (11) | −0.0037 (13) |
| C9B | 0.0302 (15) | 0.0329 (17) | 0.0297 (15) | −0.0025 (14) | 0.0030 (12) | −0.0010 (14) |
| C10B | 0.0450 (17) | 0.0268 (16) | 0.0415 (17) | 0.0015 (14) | 0.0033 (14) | −0.0005 (14) |
| C11B | 0.0441 (17) | 0.0340 (18) | 0.0453 (17) | 0.0133 (15) | 0.0121 (14) | −0.0060 (15) |
| C12B | 0.0289 (15) | 0.0395 (18) | 0.0370 (16) | 0.0082 (14) | 0.0120 (12) | −0.0032 (15) |
| ClC | 0.0340 (4) | 0.0328 (4) | 0.0580 (5) | 0.0024 (3) | 0.0091 (3) | −0.0121 (4) |
| OC | 0.0250 (11) | 0.0272 (11) | 0.0302 (11) | −0.0028 (9) | 0.0010 (8) | −0.0069 (9) |
| C1C | 0.0209 (14) | 0.0242 (15) | 0.0247 (15) | −0.0041 (12) | 0.0028 (11) | 0.0020 (13) |
| C2C | 0.0392 (16) | 0.0337 (17) | 0.0252 (16) | 0.0072 (13) | −0.0069 (12) | −0.0031 (14) |
| C3C | 0.0455 (17) | 0.0345 (17) | 0.0298 (16) | −0.0013 (14) | 0.0002 (14) | −0.0116 (14) |
| C4C | 0.0251 (15) | 0.0242 (15) | 0.0389 (16) | −0.0007 (12) | 0.0050 (13) | −0.0034 (14) |
| C5C | 0.0237 (14) | 0.0259 (15) | 0.0325 (16) | −0.0025 (12) | 0.0006 (12) | 0.0022 (13) |
| C6C | 0.0271 (15) | 0.0251 (15) | 0.0230 (14) | −0.0042 (12) | 0.0014 (12) | −0.0047 (12) |
| C7C | 0.0224 (14) | 0.0300 (16) | 0.0166 (13) | −0.0005 (13) | 0.0032 (11) | 0.0035 (12) |
| C8C | 0.0186 (14) | 0.0337 (16) | 0.0150 (13) | −0.0004 (13) | 0.0047 (11) | 0.0028 (12) |
| C9C | 0.0345 (16) | 0.0264 (15) | 0.0168 (13) | 0.0017 (13) | 0.0065 (12) | −0.0023 (12) |
| C10C | 0.0281 (16) | 0.0365 (17) | 0.0218 (14) | 0.0079 (13) | 0.0084 (12) | 0.0063 (13) |
| C11C | 0.0209 (14) | 0.0411 (17) | 0.0279 (15) | −0.0015 (14) | 0.0035 (11) | 0.0068 (14) |
| C12C | 0.0285 (15) | 0.0298 (16) | 0.0246 (14) | −0.0037 (13) | 0.0037 (12) | 0.0005 (12) |
| ClD | 0.0859 (6) | 0.0366 (5) | 0.0490 (5) | 0.0036 (4) | −0.0058 (4) | 0.0066 (4) |
| OD | 0.0362 (11) | 0.0300 (11) | 0.0319 (11) | −0.0031 (9) | 0.0156 (9) | −0.0057 (9) |
| C1D | 0.0246 (15) | 0.0364 (17) | 0.0185 (14) | 0.0036 (13) | −0.0006 (11) | −0.0031 (13) |
| C2D | 0.0316 (16) | 0.0428 (18) | 0.0271 (15) | 0.0040 (14) | 0.0066 (12) | 0.0012 (14) |
| C3D | 0.0406 (18) | 0.0421 (19) | 0.0291 (16) | −0.0061 (15) | 0.0024 (13) | 0.0049 (14) |
| C4D | 0.0564 (19) | 0.0316 (17) | 0.0223 (15) | 0.0021 (16) | −0.0021 (14) | 0.0013 (13) |
| C5D | 0.0413 (18) | 0.0438 (19) | 0.0345 (17) | 0.0120 (15) | −0.0015 (13) | 0.0012 (15) |
| C6D | 0.0336 (17) | 0.0379 (18) | 0.0322 (16) | −0.0007 (14) | 0.0022 (12) | 0.0003 (14) |
| C7D | 0.0203 (14) | 0.0328 (16) | 0.0243 (15) | 0.0020 (12) | −0.0004 (11) | −0.0050 (14) |
| C8D | 0.0167 (13) | 0.0313 (17) | 0.0281 (15) | −0.0007 (12) | 0.0022 (11) | −0.0109 (14) |
| C9D | 0.0341 (15) | 0.0285 (17) | 0.0335 (16) | −0.0044 (13) | 0.0064 (12) | −0.0047 (14) |
| C10D | 0.0429 (17) | 0.0273 (16) | 0.0446 (18) | 0.0021 (13) | −0.0017 (14) | −0.0111 (15) |
| C11D | 0.0489 (18) | 0.044 (2) | 0.0330 (18) | 0.0133 (15) | −0.0002 (14) | −0.0157 (16) |
| C12D | 0.0413 (17) | 0.052 (2) | 0.0257 (15) | 0.0079 (15) | 0.0025 (13) | −0.0043 (16) |
Geometric parameters (Å, º) top
| ClA—C4A | 1.744 (2) | C8A—C9A | 1.372 (3) |
| ClB—C4B | 1.739 (2) | C8B—C9B | 1.383 (3) |
| ClC—C4C | 1.748 (2) | C8C—C9C | 1.388 (3) |
| ClD—C4D | 1.749 (2) | C8D—C9D | 1.372 (3) |
| OA—C8A | 1.397 (2) | C9A—C10A | 1.383 (3) |
| OB—C8B | 1.381 (2) | C9B—C10B | 1.381 (3) |
| OC—C8C | 1.384 (2) | C9C—C10C | 1.378 (3) |
| OD—C8D | 1.386 (2) | C9D—C10D | 1.383 (3) |
| OA—HA | 0.82 (2) | C10A—C11A | 1.390 (3) |
| OB—HB | 0.81 (2) | C10B—C11B | 1.388 (3) |
| OC—HC | 0.79 (2) | C10C—C11C | 1.386 (3) |
| OD—HD | 0.84 (2) | C10D—C11D | 1.379 (3) |
| C1A—C2A | 1.396 (3) | C11A—C12A | 1.374 (3) |
| C1B—C2B | 1.387 (3) | C11B—C12B | 1.374 (3) |
| C1C—C2C | 1.388 (3) | C11C—C12C | 1.378 (3) |
| C1D—C2D | 1.386 (3) | C11D—C12D | 1.385 (3) |
| C1A—C6A | 1.398 (3) | C2A—H2A | 0.95 |
| C1B—C6B | 1.399 (3) | C2B—H2B | 0.95 |
| C1C—C6C | 1.394 (3) | C2C—H2C | 0.95 |
| C1D—C6D | 1.390 (3) | C2D—H2D | 0.95 |
| C1A—C7A | 1.480 (3) | C3A—H3A | 0.95 |
| C1B—C7B | 1.483 (3) | C3B—H3B | 0.95 |
| C1C—C7C | 1.479 (3) | C3C—H3C | 0.95 |
| C1D—C7D | 1.490 (3) | C3D—H3D | 0.95 |
| C2A—C3A | 1.386 (3) | C5A—H5A | 0.95 |
| C2B—C3B | 1.381 (3) | C5B—H5B | 0.95 |
| C2C—C3C | 1.385 (3) | C5C—H5C | 0.95 |
| C2D—C3D | 1.390 (3) | C5D—H5D | 0.95 |
| C3A—C4A | 1.374 (3) | C6A—H6A | 0.95 |
| C3B—C4B | 1.376 (3) | C6B—H6B | 0.95 |
| C3C—C4C | 1.378 (3) | C6C—H6C | 0.95 |
| C3D—C4D | 1.371 (3) | C6D—H6D | 0.95 |
| C4A—C5A | 1.376 (3) | C9A—H9A | 0.95 |
| C4B—C5B | 1.384 (3) | C9B—H9B | 0.95 |
| C4C—C5C | 1.379 (3) | C9C—H9C | 0.95 |
| C4D—C5D | 1.372 (3) | C9D—H9D | 0.95 |
| C5A—C6A | 1.383 (3) | C10A—H10A | 0.95 |
| C5B—C6B | 1.383 (3) | C10B—H10B | 0.95 |
| C5C—C6C | 1.381 (3) | C10C—H10C | 0.95 |
| C5D—C6D | 1.379 (3) | C10D—H10D | 0.95 |
| C7A—C8A | 1.396 (3) | C11A—H11A | 0.95 |
| C7B—C8B | 1.401 (3) | C11B—H11B | 0.95 |
| C7C—C8C | 1.396 (3) | C11C—H11C | 0.95 |
| C7D—C8D | 1.391 (3) | C11D—H11D | 0.95 |
| C7A—C12A | 1.395 (3) | C12A—H12A | 0.95 |
| C7B—C12B | 1.398 (3) | C12B—H12B | 0.95 |
| C7C—C12C | 1.394 (3) | C12C—H12C | 0.95 |
| C7D—C12D | 1.397 (3) | C12D—H12D | 0.95 |
| C8A—OA—HA | 108 (2) | C9C—C10C—C11C | 120.2 (2) |
| C8B—OB—HB | 110 (2) | C9D—C10D—C11D | 119.9 (2) |
| C8C—OC—HC | 112 (2) | C10A—C11A—C12A | 119.1 (2) |
| C8D—OD—HD | 112 (2) | C10B—C11B—C12B | 119.8 (2) |
| C2A—C1A—C6A | 117.3 (2) | C10C—C11C—C12C | 119.2 (2) |
| C2B—C1B—C6B | 117.4 (2) | C10D—C11D—C12D | 120.0 (2) |
| C2C—C1C—C6C | 117.7 (2) | C7A—C12A—C11A | 122.4 (2) |
| C2D—C1D—C6D | 118.3 (2) | C7B—C12B—C11B | 121.7 (2) |
| C2A—C1A—C7A | 120.2 (2) | C7C—C12C—C11C | 122.3 (2) |
| C2B—C1B—C7B | 120.4 (2) | C7D—C12D—C11D | 121.4 (2) |
| C2C—C1C—C7C | 120.8 (2) | C1A—C2A—H2A | 119.0 |
| C2D—C1D—C7D | 120.8 (2) | C1B—C2B—H2B | 118.8 |
| C6A—C1A—C7A | 122.3 (2) | C1C—C2C—H2C | 119.1 |
| C6B—C1B—C7B | 122.2 (2) | C1D—C2D—H2D | 119.5 |
| C6C—C1C—C7C | 121.5 (2) | C3A—C2A—H2A | 119.0 |
| C6D—C1D—C7D | 120.9 (2) | C3B—C2B—H2B | 118.8 |
| C1A—C2A—C3A | 122.1 (2) | C3C—C2C—H2C | 119.1 |
| C1B—C2B—C3B | 122.3 (2) | C3D—C2D—H2D | 119.5 |
| C1C—C2C—C3C | 121.8 (2) | C2A—C3A—H3A | 120.7 |
| C1D—C2D—C3D | 120.9 (2) | C2B—C3B—H3B | 120.6 |
| C2A—C3A—C4A | 118.6 (2) | C2C—C3C—H3C | 120.6 |
| C2B—C3B—C4B | 118.7 (2) | C2D—C3D—H3D | 120.5 |
| C2C—C3C—C4C | 118.7 (2) | C4A—C3A—H3A | 120.7 |
| C2D—C3D—C4D | 119.0 (2) | C4B—C3B—H3B | 120.6 |
| C3A—C4A—C5A | 121.2 (2) | C4C—C3C—H3C | 120.6 |
| C3B—C4B—C5B | 121.0 (2) | C4D—C3D—H3D | 120.5 |
| C3C—C4C—C5C | 121.3 (2) | C4A—C5A—H5A | 120.1 |
| C3D—C4D—C5D | 121.5 (2) | C4B—C5B—H5B | 120.4 |
| C3A—C4A—ClA | 119.2 (2) | C4C—C5C—H5C | 120.5 |
| C3B—C4B—ClB | 119.2 (2) | C4D—C5D—H5D | 120.4 |
| C3C—C4C—ClC | 119.1 (2) | C6A—C5A—H5A | 120.1 |
| C3D—C4D—ClD | 119.1 (2) | C6B—C5B—H5B | 120.4 |
| C5A—C4A—ClA | 119.6 (2) | C6C—C5C—H5C | 120.5 |
| C5B—C4B—ClB | 119.8 (2) | C6D—C5D—H5D | 120.4 |
| C5C—C4C—ClC | 119.5 (2) | C1A—C6A—H6A | 119.5 |
| C5D—C4D—ClD | 119.4 (2) | C1B—C6B—H6B | 119.4 |
| C4A—C5A—C6A | 119.8 (2) | C1C—C6C—H6C | 119.3 |
| C4B—C5B—C6B | 119.2 (2) | C1D—C6D—H6D | 119.4 |
| C4C—C5C—C6C | 119.1 (2) | C5A—C6A—H6A | 119.5 |
| C4D—C5D—C6D | 119.1 (2) | C5B—C6B—H6B | 119.4 |
| C1A—C6A—C5A | 121.0 (2) | C5C—C6C—H6C | 119.3 |
| C1B—C6B—C5B | 121.2 (2) | C5D—C6D—H6D | 119.4 |
| C1C—C6C—C5C | 121.4 (2) | C8A—C9A—H9A | 120.2 |
| C1D—C6D—C5D | 121.2 (2) | C8B—C9B—H9B | 120.1 |
| C1A—C7A—C8A | 123.2 (2) | C8C—C9C—H9C | 120.0 |
| C1B—C7B—C8B | 121.5 (2) | C8D—C9D—H9D | 120.3 |
| C1C—C7C—C8C | 123.1 (2) | C10A—C9A—H9A | 120.2 |
| C1D—C7D—C8D | 121.6 (2) | C10B—C9B—H9B | 120.1 |
| C1A—C7A—C12A | 120.2 (2) | C10C—C9C—H9C | 120.0 |
| C1B—C7B—C12B | 121.2 (2) | C10D—C9D—H9D | 120.3 |
| C1C—C7C—C12C | 119.7 (2) | C9A—C10A—H10A | 120.0 |
| C1D—C7D—C12D | 121.8 (2) | C9B—C10B—H10B | 120.0 |
| C8A—C7A—C12A | 116.6 (2) | C9C—C10C—H10C | 119.9 |
| C8B—C7B—C12B | 117.3 (2) | C9D—C10D—H10D | 120.1 |
| C8C—C7C—C12C | 117.2 (2) | C11A—C10A—H10A | 120.0 |
| C8D—C7D—C12D | 116.7 (2) | C11B—C10B—H10B | 120.0 |
| C7A—C8A—C9A | 122.1 (2) | C11C—C10C—H10C | 119.9 |
| C7B—C8B—C9B | 121.4 (2) | C11D—C10D—H10D | 120.1 |
| C7C—C8C—C9C | 121.2 (2) | C10A—C11A—H11A | 120.4 |
| C7D—C8D—C9D | 122.7 (2) | C10B—C11B—H11B | 120.1 |
| OA—C8A—C7A | 116.6 (2) | C10C—C11C—H11C | 120.4 |
| OB—C8B—C7B | 117.2 (2) | C10D—C11D—H11D | 120.0 |
| OC—C8C—C7C | 117.1 (2) | C12A—C11A—H11A | 120.4 |
| OD—C8D—C7D | 116.7 (2) | C12B—C11B—H11B | 120.1 |
| OA—C8A—C9A | 121.2 (2) | C12C—C11C—H11C | 120.4 |
| OB—C8B—C9B | 121.4 (2) | C12D—C11D—H11D | 120.0 |
| OC—C8C—C9C | 121.7 (2) | C7A—C12A—H12A | 118.8 |
| OD—C8D—C9D | 120.6 (2) | C7B—C12B—H12B | 119.2 |
| C8A—C9A—C10A | 119.7 (2) | C7C—C12C—H12C | 118.9 |
| C8B—C9B—C10B | 119.8 (2) | C7D—C12D—H12D | 119.3 |
| C8C—C9C—C10C | 120.0 (2) | C11A—C12A—H12A | 118.8 |
| C8D—C9D—C10D | 119.4 (2) | C11B—C12B—H12B | 119.2 |
| C9A—C10A—C11A | 120.0 (2) | C11C—C12C—H12C | 118.9 |
| C9B—C10B—C11B | 120.0 (2) | C11D—C12D—H12D | 119.3 |
| C6A—C1A—C2A—C3A | −0.9 (3) | ClC—C4C—C5C—C6C | 178.10 (16) |
| C6B—C1B—C2B—C3B | 2.9 (3) | ClD—C4D—C5D—C6D | 178.99 (17) |
| C6C—C1C—C2C—C3C | 0.2 (3) | C4A—C5A—C6A—C1A | −0.6 (3) |
| C6D—C1D—C2D—C3D | −0.5 (3) | C4B—C5B—C6B—C1B | −0.8 (3) |
| C7A—C1A—C2A—C3A | 176.1 (2) | C4C—C5C—C6C—C1C | 0.6 (3) |
| C7B—C1B—C2B—C3B | −177.0 (2) | C4D—C5D—C6D—C1D | −0.1 (3) |
| C7C—C1C—C2C—C3C | −178.0 (2) | C1A—C7A—C8A—C9A | 178.7 (2) |
| C7D—C1D—C2D—C3D | 178.6 (2) | C1B—C7B—C8B—C9B | −179.3 (2) |
| C2A—C1A—C6A—C5A | 1.1 (3) | C1C—C7C—C8C—C9C | −178.76 (19) |
| C2B—C1B—C6B—C5B | −2.0 (3) | C1D—C7D—C8D—C9D | 179.8 (2) |
| C2C—C1C—C6C—C5C | −0.4 (3) | C1A—C7A—C8A—OA | −4.1 (3) |
| C2D—C1D—C6D—C5D | 0.3 (3) | C1B—C7B—C8B—OB | −0.9 (3) |
| C7A—C1A—C6A—C5A | −175.8 (2) | C1C—C7C—C8C—OC | 3.8 (3) |
| C7B—C1B—C6B—C5B | 177.80 (19) | C1D—C7D—C8D—OD | 2.3 (3) |
| C7C—C1C—C6C—C5C | 177.7 (2) | C12A—C7A—C8A—C9A | −1.5 (3) |
| C7D—C1D—C6D—C5D | −178.7 (2) | C12B—C7B—C8B—C9B | −1.4 (3) |
| C2A—C1A—C7A—C8A | 133.5 (2) | C12C—C7C—C8C—C9C | 1.1 (3) |
| C2B—C1B—C7B—C8B | 127.7 (2) | C12D—C7D—C8D—C9D | −0.1 (3) |
| C2C—C1C—C7C—C8C | −130.4 (2) | C12A—C7A—C8A—OA | 175.69 (17) |
| C2D—C1D—C7D—C8D | −120.2 (2) | C12B—C7B—C8B—OB | 177.03 (18) |
| C2A—C1A—C7A—C12A | −46.3 (3) | C12C—C7C—C8C—OC | −176.39 (17) |
| C2B—C1B—C7B—C12B | −50.1 (3) | C12D—C7D—C8D—OD | −177.61 (18) |
| C2C—C1C—C7C—C12C | 49.7 (3) | C1A—C7A—C12A—C11A | −179.3 (2) |
| C2D—C1D—C7D—C12D | 59.7 (3) | C1B—C7B—C12B—C11B | 178.9 (2) |
| C6A—C1A—C7A—C8A | −49.7 (3) | C1C—C7C—C12C—C11C | 179.3 (2) |
| C6B—C1B—C7B—C8B | −52.1 (3) | C1D—C7D—C12D—C11D | 179.4 (2) |
| C6C—C1C—C7C—C8C | 51.5 (3) | C8A—C7A—C12A—C11A | 0.9 (3) |
| C6D—C1D—C7D—C8D | 58.8 (3) | C8B—C7B—C12B—C11B | 0.9 (3) |
| C6A—C1A—C7A—C12A | 130.5 (2) | C8C—C7C—C12C—C11C | −0.5 (3) |
| C6B—C1B—C7B—C12B | 130.0 (2) | C8D—C7D—C12D—C11D | −0.7 (3) |
| C6C—C1C—C7C—C12C | −128.4 (2) | C7A—C8A—C9A—C10A | 0.4 (3) |
| C6D—C1D—C7D—C12D | −121.3 (2) | C7B—C8B—C9B—C10B | 0.9 (3) |
| C1A—C2A—C3A—C4A | 0.1 (3) | C7C—C8C—C9C—C10C | −0.9 (3) |
| C1B—C2B—C3B—C4B | −0.8 (3) | C7D—C8D—C9D—C10D | 0.7 (3) |
| C1C—C2C—C3C—C4C | 0.0 (3) | OA—C8A—C9A—C10A | −176.60 (18) |
| C1D—C2D—C3D—C4D | 0.5 (3) | OB—C8B—C9B—C10B | −177.38 (19) |
| C2A—C3A—C4A—C5A | 0.4 (3) | OC—C8C—C9C—C10C | 176.45 (18) |
| C2B—C3B—C4B—C5B | −2.3 (3) | OD—C8D—C9D—C10D | 178.07 (19) |
| C2C—C3C—C4C—C5C | 0.2 (3) | C8A—C9A—C10A—C11A | 1.2 (3) |
| C2D—C3D—C4D—C5D | −0.3 (4) | C8B—C9B—C10B—C11B | 0.0 (3) |
| C2A—C3A—C4A—ClA | −179.07 (16) | C8C—C9C—C10C—C11C | 0.1 (3) |
| C2B—C3B—C4B—ClB | 178.09 (16) | C8D—C9D—C10D—C11D | −0.4 (3) |
| C2C—C3C—C4C—ClC | −178.38 (17) | C9A—C10A—C11A—C12A | −1.8 (3) |
| C2D—C3D—C4D—ClD | −179.17 (16) | C9B—C10B—C11B—C12B | −0.4 (4) |
| C3A—C4A—C5A—C6A | −0.2 (3) | C9C—C10C—C11C—C12C | 0.4 (3) |
| C3B—C4B—C5B—C6B | 3.1 (3) | C9D—C10D—C11D—C12D | −0.4 (4) |
| C3C—C4C—C5C—C6C | −0.5 (3) | C10A—C11A—C12A—C7A | 0.7 (3) |
| C3D—C4D—C5D—C6D | 0.2 (4) | C10B—C11B—C12B—C7B | 0.0 (4) |
| ClA—C4A—C5A—C6A | 179.28 (16) | C10C—C11C—C12C—C7C | −0.2 (3) |
| ClB—C4B—C5B—C6B | −177.30 (15) | C10D—C11D—C12D—C7D | 1.0 (4) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| OA—HA···OB | 0.82 (2) | 2.11 (2) | 2.899 (2) | 164 (2) |
| OB—HB···OC | 0.81 (2) | 2.11 (2) | 2.855 (2) | 154 (2) |
| OC—HC···OD | 0.79 (2) | 1.99 (2) | 2.771 (2) | 170 (2) |
| OD—HD···OA | 0.84 (3) | 2.01 (2) | 2.756 (2) | 148 (2) |
