The structures of enantiopure S,S-1,2-dicyclohexylethane-1,2-diol and its racemic compound (rac-S,S-1,2-dicyclohexylethane-1,2-diol) have been determined at 295 and 173 K. The crystals of the enantiopure material are more than 4% denser than the crystals of the racemic compound, but the melting points indicate that the crystals of the less dense racemic compound are considerably more stable than those of the racemic conglomerate. This apparent exception to the correlation of crystal density and melting point is explained. The enantiopure crystals have four molecules in the asymmetric unit (Z' = 4). Two of the molecules have the conformation observed for the one independent molecule of the racemic compound and two have a higher energy conformation; the overall P21 structure is a perturbed version of a P212121 structure with Z' = 2. The enantiopure and racemic crystals have the same hydrogen-bonding motif, but the motif in the former appears to be significantly strained. A reason why crystals of enantiopure material might be systematically less dense than crystals of its racemic compound and to be more likely to have Z' > 1 is suggested.
Supporting information
CCDC references: 612269; 612270; 612271; 612272
For all compounds, data collection: COLLECT software (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare, Cascarano, Giacovazzo, Guagliardi, Burla, Polidori & Camalli, 1994) in maXus (Mackay, Gilmore, Edwards, Tremayne, Stewart & Shankland, 1998); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL PC (Sheldrick, 1990).
(k98005)
S,
S-1,2-dicyclohexylethane-1,2-diol
top
Crystal data top
C14H26O2 | Dx = 1.084 Mg m−3 |
Mr = 226.35 | Melting point: 130-135 C K |
Monoclinic, P1211 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.540 (1) Å | Cell parameters from 49711 reflections |
b = 41.653 (6) Å | θ = 1.0–25.0° |
c = 12.025 (2) Å | µ = 0.07 mm−1 |
β = 90.33 (1)° | T = 295 K |
V = 2774.8 (8) Å3 | Needles. Long axis is a. Prism faces are {010} and {001}., colourless |
Z = 8 | 0.50 × 0.32 × 0.25 mm |
F(000) = 1008 | |
Data collection top
Nonius Kappa-CCD diffractometer | 3636 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.047 |
Graphite monochromator | θmax = 25.0°, θmin = 1.5° |
Detector resolution: 18 pixels mm-1 | h = 0→6 |
ϕ and ω scans with 1.0° steps | k = −48→49 |
9310 measured reflections | l = −14→14 |
4928 independent reflections | |
Refinement top
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)] = 0.056 | Hydrogen site location: mixed |
wR(F2) = 0.144 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0680)2 + 0.4P] where P = (Fo2 + 2Fc2)/3 |
4928 reflections | (Δ/σ)max < 0.001 |
610 parameters | Δρmax = 0.23 e Å−3 |
1 restraint | Δρmin = −0.11 e Å−3 |
Crystal data top
C14H26O2 | V = 2774.8 (8) Å3 |
Mr = 226.35 | Z = 8 |
Monoclinic, P1211 | Mo Kα radiation |
a = 5.540 (1) Å | µ = 0.07 mm−1 |
b = 41.653 (6) Å | T = 295 K |
c = 12.025 (2) Å | 0.50 × 0.32 × 0.25 mm |
β = 90.33 (1)° | |
Data collection top
Nonius Kappa-CCD diffractometer | 3636 reflections with I > 2σ(I) |
9310 measured reflections | Rint = 0.047 |
4928 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.056 | 1 restraint |
wR(F2) = 0.144 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.23 e Å−3 |
4928 reflections | Δρmin = −0.11 e Å−3 |
610 parameters | |
Special details top
Experimental. The crystal-to-detector distance was 50 mm. Each frame was measured for 100 s. The number of scan sets measured was 6; the total number of frames measured was 701. |
Refinement. Friedel reflections were merged during the refinement. The hydroxyl H atoms were located in difference maps and refined isotropically. All other H atoms were placed in calculated positions. An instruction TWIN 1 0 0 0 − 1 0 0 0 − 1 was included. The value for the volume fraction of the second individual converged to 0.0491 (15). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O01A | 0.5502 (5) | 0.09857 (8) | 0.6291 (2) | 0.0587 (8) | |
H01A | 0.732 (14) | 0.1002 (19) | 0.629 (6) | 0.14 (2)* | |
O02A | 0.0464 (5) | 0.10222 (9) | 0.6135 (3) | 0.0545 (8) | |
H02A | 0.089 (10) | 0.0872 (14) | 0.648 (5) | 0.08 (2)* | |
C01A | 0.4345 (7) | 0.12682 (10) | 0.5870 (3) | 0.0486 (10) | |
H03A | 0.5315 | 0.1455 | 0.6090 | 0.058* | |
C11A | 0.4130 (8) | 0.12667 (12) | 0.4611 (4) | 0.0600 (12) | |
H04A | 0.2802 | 0.1121 | 0.4416 | 0.072* | |
C12A | 0.6425 (11) | 0.11375 (19) | 0.4036 (4) | 0.101 (2) | |
H05A | 0.7793 | 0.1270 | 0.4246 | 0.121* | |
H06A | 0.6741 | 0.0921 | 0.4293 | 0.121* | |
C13A | 0.6181 (14) | 0.1136 (2) | 0.2778 (5) | 0.124 (3) | |
H07A | 0.7690 | 0.1066 | 0.2452 | 0.148* | |
H08A | 0.4935 | 0.0984 | 0.2560 | 0.148* | |
C14A | 0.5567 (13) | 0.1453 (3) | 0.2354 (5) | 0.132 (3) | |
H09A | 0.5347 | 0.1441 | 0.1554 | 0.158* | |
H10A | 0.6897 | 0.1599 | 0.2503 | 0.158* | |
C15A | 0.3259 (15) | 0.1589 (2) | 0.2881 (5) | 0.138 (3) | |
H11A | 0.2991 | 0.1807 | 0.2626 | 0.166* | |
H12A | 0.1880 | 0.1460 | 0.2659 | 0.166* | |
C16A | 0.3525 (13) | 0.15845 (17) | 0.4148 (4) | 0.101 (2) | |
H13A | 0.4778 | 0.1735 | 0.4361 | 0.121* | |
H14A | 0.2025 | 0.1657 | 0.4474 | 0.121* | |
C02A | 0.1899 (7) | 0.12885 (10) | 0.6469 (3) | 0.0485 (10) | |
H15A | 0.1085 | 0.1482 | 0.6195 | 0.058* | |
C21A | 0.2119 (7) | 0.13222 (10) | 0.7728 (3) | 0.0511 (10) | |
H16A | 0.3342 | 0.1169 | 0.7989 | 0.061* | |
C22A | −0.0245 (9) | 0.12469 (14) | 0.8320 (4) | 0.0734 (14) | |
H17A | −0.1507 | 0.1386 | 0.8030 | 0.088* | |
H18A | −0.0702 | 0.1027 | 0.8165 | 0.088* | |
C23A | −0.0038 (11) | 0.12935 (15) | 0.9566 (4) | 0.0848 (17) | |
H19A | −0.1583 | 0.1247 | 0.9905 | 0.102* | |
H20A | 0.1138 | 0.1143 | 0.9863 | 0.102* | |
C24A | 0.0700 (10) | 0.16261 (16) | 0.9864 (4) | 0.0880 (18) | |
H21A | 0.0877 | 0.1644 | 1.0664 | 0.106* | |
H22A | −0.0537 | 0.1776 | 0.9625 | 0.106* | |
C25A | 0.3097 (11) | 0.17095 (17) | 0.9304 (5) | 0.0945 (18) | |
H23A | 0.3503 | 0.1932 | 0.9458 | 0.113* | |
H24A | 0.4369 | 0.1575 | 0.9610 | 0.113* | |
C26A | 0.2942 (10) | 0.16591 (13) | 0.8053 (4) | 0.0725 (14) | |
H25A | 0.4516 | 0.1699 | 0.7732 | 0.087* | |
H26A | 0.1823 | 0.1814 | 0.7740 | 0.087* | |
O01B | 0.1223 (6) | 0.04371 (8) | 0.7072 (3) | 0.0573 (8) | |
H01B | −0.007 (8) | 0.0409 (10) | 0.699 (3) | 0.044 (12)* | |
O02B | 0.6364 (5) | 0.03755 (9) | 0.7061 (3) | 0.0600 (8) | |
H02B | 0.579 (8) | 0.0552 (12) | 0.695 (4) | 0.052 (15)* | |
C01B | 0.2393 (6) | 0.01459 (11) | 0.6755 (3) | 0.0477 (10) | |
H03B | 0.1377 | −0.0035 | 0.6980 | 0.057* | |
C11B | 0.2722 (7) | 0.01321 (12) | 0.5484 (4) | 0.0567 (11) | |
H04B | 0.3963 | 0.0289 | 0.5282 | 0.068* | |
C12B | 0.0429 (9) | 0.02177 (15) | 0.4859 (4) | 0.0738 (14) | |
H05B | −0.0078 | 0.0432 | 0.5072 | 0.089* | |
H06B | −0.0840 | 0.0069 | 0.5067 | 0.089* | |
C13B | 0.0765 (12) | 0.02059 (16) | 0.3607 (5) | 0.0930 (18) | |
H07B | −0.0754 | 0.0257 | 0.3242 | 0.112* | |
H08B | 0.1936 | 0.0367 | 0.3390 | 0.112* | |
C14B | 0.1611 (11) | −0.01180 (16) | 0.3226 (4) | 0.0892 (17) | |
H09B | 0.0347 | −0.0275 | 0.3350 | 0.107* | |
H10B | 0.1936 | −0.0111 | 0.2435 | 0.107* | |
C15B | 0.3852 (12) | −0.02195 (19) | 0.3838 (5) | 0.102 (2) | |
H11B | 0.5188 | −0.0085 | 0.3608 | 0.122* | |
H12B | 0.4237 | −0.0439 | 0.3639 | 0.122* | |
C16B | 0.3568 (10) | −0.01960 (13) | 0.5104 (4) | 0.0769 (14) | |
H13B | 0.2417 | −0.0356 | 0.5346 | 0.092* | |
H14B | 0.5106 | −0.0244 | 0.5456 | 0.092* | |
C02B | 0.4756 (7) | 0.01299 (11) | 0.7407 (3) | 0.0515 (10) | |
H15B | 0.5518 | −0.0073 | 0.7197 | 0.062* | |
C21B | 0.4514 (7) | 0.01204 (11) | 0.8674 (3) | 0.0584 (11) | |
H16B | 0.3136 | −0.0018 | 0.8845 | 0.070* | |
C22B | 0.4054 (11) | 0.04457 (15) | 0.9226 (4) | 0.0858 (16) | |
H17B | 0.5342 | 0.0592 | 0.9028 | 0.103* | |
H18B | 0.2552 | 0.0534 | 0.8941 | 0.103* | |
C23B | 0.3912 (12) | 0.04234 (19) | 1.0477 (5) | 0.108 (2) | |
H19B | 0.2505 | 0.0299 | 1.0683 | 0.129* | |
H20B | 0.3735 | 0.0637 | 1.0788 | 0.129* | |
C24B | 0.6167 (12) | 0.0267 (2) | 1.0957 (5) | 0.107 (2) | |
H21B | 0.7541 | 0.0406 | 1.0829 | 0.128* | |
H22B | 0.5980 | 0.0243 | 1.1755 | 0.128* | |
C25B | 0.6661 (12) | −0.00526 (19) | 1.0465 (5) | 0.101 (2) | |
H23B | 0.5401 | −0.0201 | 1.0680 | 0.121* | |
H24B | 0.8184 | −0.0133 | 1.0752 | 0.121* | |
C26B | 0.6773 (9) | −0.00343 (15) | 0.9204 (4) | 0.0777 (15) | |
H25B | 0.6963 | −0.0249 | 0.8909 | 0.093* | |
H26B | 0.8184 | 0.0089 | 0.8994 | 0.093* | |
O01C | 1.0526 (5) | 0.30180 (8) | 0.9532 (2) | 0.0588 (8) | |
H01C | 1.197 (9) | 0.3004 (11) | 0.968 (3) | 0.055 (12)* | |
O02C | 0.5493 (5) | 0.29855 (8) | 0.9667 (2) | 0.0540 (7) | |
H02C | 0.613 (10) | 0.3155 (13) | 0.937 (4) | 0.081 (18)* | |
C01C | 0.9375 (6) | 0.27359 (10) | 0.9935 (3) | 0.0471 (10) | |
H03C | 1.0337 | 0.2550 | 0.9711 | 0.057* | |
C11C | 0.9191 (7) | 0.27366 (12) | 1.1204 (3) | 0.0576 (11) | |
H04C | 0.7888 | 0.2885 | 1.1402 | 0.069* | |
C12C | 1.1478 (10) | 0.28570 (18) | 1.1772 (4) | 0.0920 (19) | |
H05C | 1.1819 | 0.3074 | 1.1523 | 0.110* | |
H06C | 1.2826 | 0.2722 | 1.1561 | 0.110* | |
C13C | 1.1219 (13) | 0.2855 (2) | 1.3053 (5) | 0.115 (2) | |
H07C | 1.2727 | 0.2923 | 1.3391 | 0.138* | |
H08C | 0.9976 | 0.3006 | 1.3268 | 0.138* | |
C14C | 1.0596 (14) | 0.2538 (2) | 1.3465 (5) | 0.126 (3) | |
H09C | 1.0390 | 0.2547 | 1.4265 | 0.151* | |
H10C | 1.1904 | 0.2390 | 1.3309 | 0.151* | |
C15C | 0.8300 (14) | 0.2416 (2) | 1.2931 (5) | 0.129 (3) | |
H11C | 0.6958 | 0.2551 | 1.3147 | 0.155* | |
H12C | 0.7976 | 0.2199 | 1.3188 | 0.155* | |
C16C | 0.8534 (13) | 0.24160 (17) | 1.1649 (5) | 0.098 (2) | |
H13C | 0.9756 | 0.2262 | 1.1433 | 0.117* | |
H14C | 0.7012 | 0.2349 | 1.1320 | 0.117* | |
C02C | 0.6926 (6) | 0.27175 (10) | 0.9343 (3) | 0.0485 (10) | |
H15C | 0.6113 | 0.2524 | 0.9618 | 0.058* | |
C21C | 0.7104 (7) | 0.26839 (11) | 0.8071 (3) | 0.0513 (10) | |
H16C | 0.8309 | 0.2838 | 0.7809 | 0.062* | |
C22C | 0.4734 (8) | 0.27576 (13) | 0.7486 (4) | 0.0676 (12) | |
H17C | 0.4266 | 0.2977 | 0.7651 | 0.081* | |
H18C | 0.3491 | 0.2616 | 0.7772 | 0.081* | |
C23C | 0.4892 (11) | 0.27161 (16) | 0.6232 (4) | 0.0854 (16) | |
H19C | 0.3326 | 0.2758 | 0.5897 | 0.103* | |
H20C | 0.6035 | 0.2869 | 0.5932 | 0.103* | |
C24C | 0.5686 (11) | 0.23801 (16) | 0.5947 (4) | 0.0860 (17) | |
H21C | 0.5858 | 0.2361 | 0.5148 | 0.103* | |
H22C | 0.4466 | 0.2228 | 0.6185 | 0.103* | |
C25C | 0.8075 (11) | 0.23010 (16) | 0.6511 (4) | 0.0882 (17) | |
H23C | 0.8498 | 0.2080 | 0.6354 | 0.106* | |
H24C | 0.9331 | 0.2437 | 0.6207 | 0.106* | |
C26C | 0.7959 (9) | 0.23490 (12) | 0.7758 (4) | 0.0680 (13) | |
H25C | 0.9548 | 0.2313 | 0.8077 | 0.082* | |
H26C | 0.6869 | 0.2192 | 0.8073 | 0.082* | |
O01D | 0.6244 (5) | 0.35685 (7) | 0.8702 (2) | 0.0538 (8) | |
H01D | 0.476 (9) | 0.3591 (11) | 0.869 (3) | 0.058 (13)* | |
O02D | 1.1421 (5) | 0.36212 (10) | 0.8746 (3) | 0.0601 (9) | |
H02D | 1.079 (11) | 0.3472 (14) | 0.870 (5) | 0.08 (2)* | |
C01D | 0.7453 (7) | 0.38610 (11) | 0.9012 (4) | 0.0522 (10) | |
H03D | 0.6453 | 0.4043 | 0.8776 | 0.063* | |
C11D | 0.7801 (7) | 0.38780 (11) | 1.0283 (4) | 0.0543 (10) | |
H04D | 0.9007 | 0.3716 | 1.0487 | 0.065* | |
C12D | 0.5510 (9) | 0.37994 (15) | 1.0912 (4) | 0.0796 (16) | |
H05D | 0.4958 | 0.3587 | 1.0699 | 0.095* | |
H06D | 0.4262 | 0.3952 | 1.0707 | 0.095* | |
C13D | 0.5899 (11) | 0.38097 (15) | 1.2164 (4) | 0.0853 (17) | |
H07D | 0.4381 | 0.3767 | 1.2533 | 0.102* | |
H08D | 0.7035 | 0.3643 | 1.2378 | 0.102* | |
C14D | 0.6851 (11) | 0.41314 (17) | 1.2536 (5) | 0.0931 (18) | |
H09D | 0.5640 | 0.4295 | 1.2400 | 0.112* | |
H10D | 0.7185 | 0.4126 | 1.3328 | 0.112* | |
C15D | 0.9123 (11) | 0.42142 (17) | 1.1918 (5) | 0.0954 (18) | |
H11D | 1.0391 | 0.4066 | 1.2132 | 0.115* | |
H12D | 0.9637 | 0.4429 | 1.2125 | 0.115* | |
C16D | 0.8762 (10) | 0.41996 (14) | 1.0660 (4) | 0.0803 (15) | |
H13D | 0.7642 | 0.4367 | 1.0435 | 0.096* | |
H14D | 1.0292 | 0.4241 | 1.0298 | 0.096* | |
C02D | 0.9813 (6) | 0.38702 (11) | 0.8366 (3) | 0.0498 (10) | |
H15D | 1.0592 | 0.4074 | 0.8565 | 0.060* | |
C21D | 0.9610 (7) | 0.38691 (11) | 0.7094 (4) | 0.0575 (11) | |
H16D | 0.8297 | 0.4016 | 0.6890 | 0.069* | |
C22D | 0.9048 (10) | 0.35462 (14) | 0.6570 (4) | 0.0794 (15) | |
H17D | 0.7512 | 0.3469 | 0.6847 | 0.095* | |
H18D | 1.0280 | 0.3393 | 0.6789 | 0.095* | |
C23D | 0.8934 (11) | 0.35638 (18) | 0.5301 (4) | 0.100 (2) | |
H19D | 0.8648 | 0.3351 | 0.5002 | 0.120* | |
H20D | 0.7597 | 0.3700 | 0.5077 | 0.120* | |
C24D | 1.1258 (11) | 0.36964 (19) | 0.4831 (5) | 0.0972 (19) | |
H21D | 1.2566 | 0.3548 | 0.4986 | 0.117* | |
H22D | 1.1102 | 0.3717 | 0.4031 | 0.117* | |
C25D | 1.1847 (11) | 0.40159 (16) | 0.5324 (5) | 0.0911 (18) | |
H23D | 1.0635 | 0.4171 | 0.5093 | 0.109* | |
H24D | 1.3395 | 0.4088 | 0.5046 | 0.109* | |
C26D | 1.1942 (8) | 0.40033 (13) | 0.6586 (4) | 0.0683 (13) | |
H25D | 1.2220 | 0.4218 | 0.6872 | 0.082* | |
H26D | 1.3291 | 0.3870 | 0.6816 | 0.082* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O01A | 0.0379 (15) | 0.070 (2) | 0.0682 (19) | 0.0040 (14) | 0.0042 (13) | 0.0135 (15) |
O02A | 0.0380 (14) | 0.065 (2) | 0.0603 (19) | 0.0007 (15) | 0.0013 (12) | −0.0006 (17) |
C01A | 0.040 (2) | 0.058 (3) | 0.048 (2) | −0.0002 (18) | −0.0012 (17) | 0.0033 (19) |
C11A | 0.045 (2) | 0.087 (4) | 0.048 (3) | 0.000 (2) | 0.0008 (18) | −0.001 (2) |
C12A | 0.084 (4) | 0.161 (6) | 0.058 (3) | 0.034 (4) | 0.013 (3) | −0.003 (4) |
C13A | 0.116 (5) | 0.196 (9) | 0.059 (4) | 0.038 (5) | 0.014 (3) | −0.027 (5) |
C14A | 0.101 (5) | 0.233 (10) | 0.062 (4) | 0.027 (6) | 0.019 (3) | 0.028 (5) |
C15A | 0.150 (7) | 0.198 (9) | 0.065 (4) | 0.053 (6) | 0.010 (4) | 0.028 (5) |
C16A | 0.121 (5) | 0.118 (5) | 0.063 (4) | 0.042 (4) | 0.014 (3) | 0.018 (3) |
C02A | 0.044 (2) | 0.051 (3) | 0.051 (2) | 0.0015 (19) | 0.0001 (17) | −0.0012 (19) |
C21A | 0.046 (2) | 0.060 (3) | 0.047 (2) | 0.0092 (19) | 0.0025 (17) | 0.003 (2) |
C22A | 0.062 (3) | 0.098 (4) | 0.060 (3) | −0.007 (3) | 0.015 (2) | −0.003 (3) |
C23A | 0.090 (4) | 0.111 (5) | 0.054 (3) | 0.010 (3) | 0.017 (3) | 0.003 (3) |
C24A | 0.099 (4) | 0.113 (5) | 0.052 (3) | 0.032 (4) | 0.003 (3) | −0.014 (3) |
C25A | 0.097 (4) | 0.114 (5) | 0.072 (4) | −0.005 (4) | 0.000 (3) | −0.024 (3) |
C26A | 0.083 (3) | 0.078 (4) | 0.057 (3) | −0.007 (3) | 0.013 (2) | −0.012 (2) |
O01B | 0.0335 (15) | 0.069 (2) | 0.070 (2) | 0.0002 (15) | −0.0061 (14) | −0.0047 (15) |
O02B | 0.0335 (14) | 0.070 (2) | 0.076 (2) | −0.0002 (16) | 0.0004 (13) | 0.0163 (17) |
C01B | 0.0353 (18) | 0.060 (3) | 0.048 (2) | −0.0035 (19) | 0.0000 (16) | 0.005 (2) |
C11B | 0.051 (2) | 0.065 (3) | 0.054 (3) | −0.006 (2) | −0.0014 (19) | 0.006 (2) |
C12B | 0.070 (3) | 0.099 (4) | 0.052 (3) | 0.013 (3) | −0.011 (2) | −0.004 (3) |
C13B | 0.099 (4) | 0.103 (5) | 0.076 (4) | −0.001 (4) | −0.030 (3) | −0.002 (3) |
C14B | 0.101 (4) | 0.112 (5) | 0.055 (3) | −0.004 (4) | −0.004 (3) | −0.011 (3) |
C15B | 0.101 (5) | 0.125 (6) | 0.080 (4) | 0.026 (4) | 0.007 (3) | −0.026 (4) |
C16B | 0.088 (3) | 0.088 (4) | 0.055 (3) | 0.017 (3) | −0.007 (2) | −0.008 (3) |
C02B | 0.041 (2) | 0.057 (3) | 0.057 (3) | 0.0000 (19) | 0.0030 (17) | 0.004 (2) |
C21B | 0.048 (2) | 0.076 (3) | 0.051 (3) | 0.000 (2) | −0.0036 (18) | 0.006 (2) |
C22B | 0.089 (4) | 0.098 (4) | 0.070 (4) | 0.020 (3) | −0.020 (3) | −0.013 (3) |
C23B | 0.103 (4) | 0.160 (6) | 0.059 (4) | 0.032 (4) | −0.015 (3) | −0.018 (4) |
C24B | 0.096 (4) | 0.158 (7) | 0.066 (4) | 0.004 (4) | −0.028 (3) | −0.006 (4) |
C25B | 0.095 (4) | 0.136 (6) | 0.070 (4) | 0.014 (4) | −0.025 (3) | 0.023 (4) |
C26B | 0.066 (3) | 0.102 (4) | 0.065 (3) | 0.021 (3) | −0.015 (2) | 0.009 (3) |
O01C | 0.0352 (15) | 0.071 (2) | 0.070 (2) | −0.0017 (14) | −0.0044 (13) | 0.0165 (16) |
O02C | 0.0362 (14) | 0.067 (2) | 0.0589 (18) | 0.0003 (14) | 0.0025 (12) | −0.0022 (16) |
C01C | 0.040 (2) | 0.057 (3) | 0.045 (2) | −0.0029 (18) | 0.0036 (16) | 0.0018 (19) |
C11C | 0.045 (2) | 0.079 (3) | 0.049 (3) | −0.001 (2) | 0.0010 (18) | 0.002 (2) |
C12C | 0.077 (3) | 0.144 (6) | 0.055 (3) | −0.024 (3) | −0.015 (2) | −0.002 (3) |
C13C | 0.111 (5) | 0.166 (8) | 0.067 (4) | −0.021 (5) | −0.019 (4) | −0.023 (4) |
C14C | 0.124 (6) | 0.206 (9) | 0.049 (4) | −0.023 (6) | −0.011 (3) | 0.018 (4) |
C15C | 0.131 (6) | 0.200 (8) | 0.056 (4) | −0.056 (6) | −0.008 (4) | 0.035 (4) |
C16C | 0.120 (5) | 0.112 (5) | 0.061 (3) | −0.031 (4) | −0.012 (3) | 0.017 (3) |
C02C | 0.0397 (19) | 0.052 (3) | 0.054 (2) | −0.0019 (19) | −0.0001 (17) | 0.0025 (19) |
C21C | 0.046 (2) | 0.064 (3) | 0.044 (2) | −0.007 (2) | −0.0001 (17) | 0.0022 (19) |
C22C | 0.063 (3) | 0.083 (4) | 0.056 (3) | 0.001 (2) | −0.012 (2) | −0.001 (2) |
C23C | 0.095 (4) | 0.107 (5) | 0.054 (3) | −0.007 (3) | −0.024 (3) | 0.002 (3) |
C24C | 0.100 (4) | 0.107 (5) | 0.051 (3) | −0.018 (4) | −0.005 (3) | −0.009 (3) |
C25C | 0.093 (4) | 0.110 (5) | 0.061 (3) | 0.010 (3) | −0.003 (3) | −0.028 (3) |
C26C | 0.069 (3) | 0.075 (3) | 0.059 (3) | 0.001 (2) | −0.008 (2) | −0.012 (2) |
O01D | 0.0316 (14) | 0.069 (2) | 0.0613 (18) | −0.0027 (14) | 0.0054 (12) | −0.0095 (14) |
O02D | 0.0348 (15) | 0.070 (3) | 0.076 (2) | 0.0011 (16) | 0.0039 (13) | 0.0115 (18) |
C01D | 0.040 (2) | 0.054 (3) | 0.062 (3) | 0.0021 (19) | 0.0025 (18) | −0.005 (2) |
C11D | 0.049 (2) | 0.054 (3) | 0.060 (3) | 0.002 (2) | 0.0026 (19) | −0.007 (2) |
C12D | 0.067 (3) | 0.105 (5) | 0.067 (3) | −0.018 (3) | 0.018 (2) | −0.014 (3) |
C13D | 0.092 (4) | 0.110 (5) | 0.054 (3) | −0.006 (3) | 0.023 (3) | −0.011 (3) |
C14D | 0.100 (4) | 0.116 (5) | 0.063 (3) | 0.010 (4) | 0.004 (3) | −0.028 (3) |
C15D | 0.098 (4) | 0.110 (5) | 0.079 (4) | −0.013 (4) | −0.003 (3) | −0.033 (3) |
C16D | 0.087 (3) | 0.076 (4) | 0.078 (4) | −0.009 (3) | 0.009 (3) | −0.018 (3) |
C02D | 0.0332 (18) | 0.058 (3) | 0.059 (3) | 0.0000 (18) | 0.0031 (17) | 0.005 (2) |
C21D | 0.046 (2) | 0.064 (3) | 0.063 (3) | 0.002 (2) | 0.0089 (19) | 0.011 (2) |
C22D | 0.085 (3) | 0.095 (4) | 0.058 (3) | −0.029 (3) | 0.020 (2) | −0.011 (3) |
C23D | 0.100 (4) | 0.142 (6) | 0.059 (3) | −0.030 (4) | 0.018 (3) | −0.022 (3) |
C24D | 0.091 (4) | 0.141 (6) | 0.059 (3) | −0.008 (4) | 0.025 (3) | −0.005 (4) |
C25D | 0.091 (4) | 0.105 (5) | 0.078 (4) | −0.006 (3) | 0.028 (3) | 0.020 (3) |
C26D | 0.062 (3) | 0.077 (3) | 0.066 (3) | −0.007 (2) | 0.011 (2) | 0.014 (2) |
Geometric parameters (Å, º) top
O01A—C01A | 1.431 (5) | C15A—H12A | 0.97 |
O02A—C02A | 1.421 (5) | C16A—H13A | 0.97 |
C01A—C02A | 1.541 (5) | C16A—H14A | 0.97 |
C01A—C11A | 1.518 (6) | C21A—H16A | 0.98 |
C02A—C21A | 1.525 (6) | C22A—H17A | 0.97 |
C11A—C12A | 1.548 (7) | C22A—H18A | 0.97 |
C11A—C16A | 1.474 (8) | C23A—H19A | 0.97 |
C12A—C13A | 1.518 (8) | C23A—H20A | 0.97 |
C13A—C14A | 1.458 (11) | C24A—H21A | 0.97 |
C14A—C15A | 1.538 (10) | C24A—H22A | 0.97 |
C15A—C16A | 1.529 (8) | C25A—H23A | 0.97 |
C21A—C22A | 1.526 (6) | C25A—H24A | 0.97 |
C21A—C26A | 1.526 (7) | C26A—H25A | 0.97 |
C22A—C23A | 1.515 (7) | C26A—H26A | 0.97 |
C23A—C24A | 1.488 (9) | C01B—H03B | 0.98 |
C24A—C25A | 1.532 (8) | C02B—H15B | 0.98 |
C25A—C26A | 1.521 (7) | C11B—H04B | 0.98 |
O01B—C01B | 1.429 (5) | C12B—H05B | 0.97 |
O02B—C02B | 1.420 (5) | C12B—H06B | 0.97 |
C01B—C02B | 1.524 (5) | C13B—H07B | 0.97 |
C01B—C11B | 1.541 (6) | C13B—H08B | 0.97 |
C02B—C21B | 1.530 (6) | C14B—H09B | 0.97 |
C11B—C12B | 1.515 (6) | C14B—H10B | 0.97 |
C11B—C16B | 1.516 (7) | C15B—H11B | 0.97 |
C12B—C13B | 1.519 (7) | C15B—H12B | 0.97 |
C13B—C14B | 1.500 (9) | C16B—H13B | 0.97 |
C14B—C15B | 1.500 (8) | C16B—H14B | 0.97 |
C15B—C16B | 1.535 (7) | C21B—H16B | 0.98 |
C21B—C22B | 1.531 (7) | C22B—H17B | 0.97 |
C21B—C26B | 1.543 (6) | C22B—H18B | 0.97 |
C22B—C23B | 1.510 (7) | C23B—H19B | 0.97 |
C23B—C24B | 1.521 (9) | C23B—H20B | 0.97 |
C24B—C25B | 1.481 (10) | C24B—H21B | 0.97 |
C25B—C26B | 1.520 (7) | C24B—H22B | 0.97 |
O01C—C01C | 1.423 (5) | C25B—H23B | 0.97 |
O02C—C02C | 1.425 (5) | C25B—H24B | 0.97 |
C01C—C02C | 1.530 (5) | C26B—H25B | 0.97 |
C01C—C11C | 1.530 (6) | C26B—H26B | 0.97 |
C02C—C21C | 1.540 (6) | C01C—H03C | 0.98 |
C11C—C12C | 1.521 (7) | C02C—H15C | 0.98 |
C11C—C16C | 1.484 (8) | C11C—H04C | 0.98 |
C12C—C13C | 1.549 (8) | C12C—H05C | 0.97 |
C13C—C14C | 1.451 (11) | C12C—H06C | 0.97 |
C14C—C15C | 1.510 (10) | C13C—H07C | 0.97 |
C15C—C16C | 1.548 (8) | C13C—H08C | 0.97 |
C21C—C22C | 1.517 (6) | C14C—H09C | 0.97 |
C21C—C26C | 1.521 (7) | C14C—H10C | 0.97 |
C22C—C23C | 1.521 (7) | C15C—H11C | 0.97 |
C23C—C24C | 1.507 (9) | C15C—H12C | 0.97 |
C24C—C25C | 1.520 (8) | C16C—H13C | 0.97 |
C25C—C26C | 1.514 (7) | C16C—H14C | 0.97 |
O01D—C01D | 1.438 (5) | C21C—H16C | 0.98 |
O02D—C02D | 1.440 (5) | C22C—H17C | 0.97 |
C01D—C02D | 1.525 (5) | C22C—H18C | 0.97 |
C01D—C11D | 1.541 (6) | C23C—H19C | 0.97 |
C02D—C21D | 1.534 (6) | C23C—H20C | 0.97 |
C11D—C12D | 1.517 (6) | C24C—H21C | 0.97 |
C11D—C16D | 1.510 (7) | C24C—H22C | 0.97 |
C12D—C13D | 1.520 (7) | C25C—H23C | 0.97 |
C13D—C14D | 1.507 (9) | C25C—H24C | 0.97 |
C14D—C15D | 1.506 (8) | C26C—H25C | 0.97 |
C15D—C16D | 1.525 (7) | C26C—H26C | 0.97 |
C21D—C22D | 1.517 (7) | C01D—H03D | 0.98 |
C21D—C26D | 1.537 (6) | C02D—H15D | 0.98 |
C22D—C23D | 1.528 (7) | C11D—H04D | 0.98 |
C23D—C24D | 1.513 (8) | C12D—H05D | 0.97 |
C24D—C25D | 1.492 (9) | C12D—H06D | 0.97 |
C25D—C26D | 1.518 (7) | C13D—H07D | 0.97 |
O01A—H01A | 1.01 (8) | C13D—H08D | 0.97 |
O02A—H02A | 0.79 (6) | C14D—H09D | 0.97 |
O01B—H01B | 0.73 (4) | C14D—H10D | 0.97 |
O02B—H02B | 0.81 (5) | C15D—H11D | 0.97 |
O01C—H01C | 0.82 (5) | C15D—H12D | 0.97 |
O02C—H02C | 0.87 (6) | C16D—H13D | 0.97 |
O01D—H01D | 0.83 (5) | C16D—H14D | 0.97 |
O02D—H02D | 0.72 (6) | C21D—H16D | 0.98 |
C01A—H03A | 0.98 | C22D—H17D | 0.97 |
C02A—H15A | 0.98 | C22D—H18D | 0.97 |
C11A—H04A | 0.98 | C23D—H19D | 0.97 |
C12A—H05A | 0.97 | C23D—H20D | 0.97 |
C12A—H06A | 0.97 | C24D—H21D | 0.97 |
C13A—H07A | 0.97 | C24D—H22D | 0.97 |
C13A—H08A | 0.97 | C25D—H23D | 0.97 |
C14A—H09A | 0.97 | C25D—H24D | 0.97 |
C14A—H10A | 0.97 | C26D—H25D | 0.97 |
C15A—H11A | 0.97 | C26D—H26D | 0.97 |
| | | |
O01A—C01A—C02A | 105.9 (3) | C16B—C15B—H12B | 109.2 |
O01A—C01A—C11A | 112.4 (3) | C11B—C16B—H13B | 109.0 |
C02A—C01A—C11A | 113.7 (3) | C11B—C16B—H14B | 109.0 |
O02A—C02A—C01A | 108.5 (3) | C15B—C16B—H13B | 109.0 |
O02A—C02A—C21A | 113.2 (3) | C15B—C16B—H14B | 109.0 |
C01A—C02A—C21A | 113.8 (3) | C02B—C21B—H16B | 107.3 |
C01A—C11A—C12A | 112.8 (4) | C22B—C21B—H16B | 107.3 |
C01A—C11A—C16A | 112.9 (4) | C26B—C21B—H16B | 107.3 |
C12A—C11A—C16A | 109.2 (5) | C21B—C22B—H17B | 109.0 |
C11A—C12A—C13A | 112.2 (5) | C21B—C22B—H18B | 109.0 |
C12A—C13A—C14A | 111.3 (6) | C23B—C22B—H17B | 109.0 |
C13A—C14A—C15A | 112.4 (6) | C23B—C22B—H18B | 109.0 |
C14A—C15A—C16A | 109.3 (6) | C22B—C23B—H19B | 109.4 |
C11A—C16A—C15A | 114.0 (6) | C22B—C23B—H20B | 109.4 |
C02A—C21A—C22A | 112.3 (4) | C24B—C23B—H19B | 109.4 |
C02A—C21A—C26A | 111.2 (3) | C24B—C23B—H20B | 109.4 |
C22A—C21A—C26A | 109.0 (4) | C23B—C24B—H21B | 109.0 |
C21A—C22A—C23A | 112.0 (4) | C23B—C24B—H22B | 109.0 |
C22A—C23A—C24A | 112.1 (5) | C25B—C24B—H21B | 109.0 |
C23A—C24A—C25A | 110.0 (5) | C25B—C24B—H22B | 109.0 |
C24A—C25A—C26A | 111.1 (5) | C24B—C25B—H23B | 109.4 |
C21A—C26A—C25A | 113.3 (4) | C24B—C25B—H24B | 109.4 |
O01B—C01B—C02B | 106.8 (3) | C26B—C25B—H23B | 109.4 |
O01B—C01B—C11B | 110.7 (3) | C26B—C25B—H24B | 109.4 |
C02B—C01B—C11B | 113.7 (3) | C21B—C26B—H25B | 108.9 |
O02B—C02B—C01B | 110.9 (3) | C21B—C26B—H26B | 108.9 |
O02B—C02B—C21B | 111.6 (3) | C25B—C26B—H25B | 108.9 |
C01B—C02B—C21B | 115.7 (3) | C25B—C26B—H26B | 108.9 |
C01B—C11B—C12B | 112.3 (3) | O01C—C01C—H03C | 108.3 |
C01B—C11B—C16B | 111.8 (4) | C02C—C01C—H03C | 108.3 |
C12B—C11B—C16B | 108.8 (4) | C11C—C01C—H03C | 108.3 |
C11B—C12B—C13B | 112.1 (4) | O02C—C02C—H15C | 107.0 |
C12B—C13B—C14B | 111.8 (5) | C01C—C02C—H15C | 107.0 |
C13B—C14B—C15B | 111.3 (5) | C21C—C02C—H15C | 107.0 |
C14B—C15B—C16B | 112.3 (5) | C01C—C11C—H04C | 107.2 |
C11B—C16B—C15B | 113.0 (5) | C12C—C11C—H04C | 107.2 |
C02B—C21B—C22B | 115.1 (4) | C16C—C11C—H04C | 107.2 |
C02B—C21B—C26B | 110.3 (3) | C11C—C12C—H05C | 109.4 |
C22B—C21B—C26B | 109.1 (4) | C11C—C12C—H06C | 109.4 |
C21B—C22B—C23B | 112.8 (5) | C13C—C12C—H05C | 109.4 |
C22B—C23B—C24B | 110.9 (5) | C13C—C12C—H06C | 109.4 |
C23B—C24B—C25B | 112.8 (5) | C12C—C13C—H07C | 109.3 |
C24B—C25B—C26B | 111.3 (5) | C12C—C13C—H08C | 109.3 |
C21B—C26B—C25B | 113.3 (4) | C14C—C13C—H07C | 109.3 |
O01C—C01C—C02C | 106.3 (3) | C14C—C13C—H08C | 109.3 |
O01C—C01C—C11C | 111.8 (3) | C13C—C14C—H09C | 109.4 |
C02C—C01C—C11C | 113.6 (3) | C13C—C14C—H10C | 109.4 |
O02C—C02C—C01C | 109.1 (3) | C15C—C14C—H09C | 109.4 |
O02C—C02C—C21C | 112.5 (3) | C15C—C14C—H10C | 109.4 |
C01C—C02C—C21C | 113.9 (3) | C14C—C15C—H11C | 109.6 |
C01C—C11C—C12C | 112.8 (4) | C14C—C15C—H12C | 109.6 |
C01C—C11C—C16C | 112.0 (4) | C16C—C15C—H11C | 109.6 |
C12C—C11C—C16C | 109.9 (5) | C16C—C15C—H12C | 109.6 |
C11C—C12C—C13C | 111.3 (5) | C11C—C16C—H13C | 109.1 |
C12C—C13C—C14C | 111.7 (6) | C11C—C16C—H14C | 109.1 |
C13C—C14C—C15C | 111.3 (6) | C15C—C16C—H13C | 109.1 |
C14C—C15C—C16C | 110.4 (6) | C15C—C16C—H14C | 109.1 |
C11C—C16C—C15C | 112.4 (6) | C02C—C21C—H16C | 107.9 |
C02C—C21C—C22C | 112.4 (3) | C22C—C21C—H16C | 107.9 |
C02C—C21C—C26C | 110.6 (3) | C26C—C21C—H16C | 107.9 |
C22C—C21C—C26C | 109.9 (4) | C21C—C22C—H17C | 109.1 |
C21C—C22C—C23C | 112.5 (4) | C21C—C22C—H18C | 109.1 |
C22C—C23C—C24C | 110.5 (5) | C23C—C22C—H17C | 109.1 |
C23C—C24C—C25C | 110.8 (5) | C23C—C22C—H18C | 109.1 |
C24C—C25C—C26C | 111.8 (5) | C22C—C23C—H19C | 109.6 |
C21C—C26C—C25C | 112.4 (4) | C22C—C23C—H20C | 109.6 |
O01D—C01D—C02D | 106.8 (3) | C24C—C23C—H19C | 109.6 |
O01D—C01D—C11D | 110.6 (3) | C24C—C23C—H20C | 109.6 |
C02D—C01D—C11D | 113.7 (3) | C23C—C24C—H21C | 109.5 |
O02D—C02D—C01D | 110.6 (3) | C23C—C24C—H22C | 109.5 |
O02D—C02D—C21D | 110.8 (3) | C25C—C24C—H21C | 109.5 |
C01D—C02D—C21D | 116.7 (3) | C25C—C24C—H22C | 109.5 |
C01D—C11D—C12D | 112.6 (4) | C24C—C25C—H23C | 109.3 |
C01D—C11D—C16D | 112.4 (4) | C24C—C25C—H24C | 109.3 |
C12D—C11D—C16D | 109.7 (4) | C26C—C25C—H23C | 109.3 |
C11D—C12D—C13D | 111.9 (4) | C26C—C25C—H24C | 109.3 |
C12D—C13D—C14D | 111.5 (5) | C21C—C26C—H25C | 109.1 |
C13D—C14D—C15D | 110.4 (5) | C21C—C26C—H26C | 109.1 |
C14D—C15D—C16D | 112.0 (5) | C25C—C26C—H25C | 109.1 |
C11D—C16D—C15D | 112.2 (5) | C25C—C26C—H26C | 109.1 |
C02D—C21D—C22D | 115.5 (4) | O01D—C01D—H03D | 108.6 |
C02D—C21D—C26D | 109.8 (4) | C02D—C01D—H03D | 108.6 |
C22D—C21D—C26D | 109.2 (4) | C11D—C01D—H03D | 108.6 |
C21D—C22D—C23D | 112.3 (5) | O02D—C02D—H15D | 106.0 |
C22D—C23D—C24D | 111.1 (5) | C01D—C02D—H15D | 106.0 |
C23D—C24D—C25D | 111.2 (5) | C21D—C02D—H15D | 106.0 |
C24D—C25D—C26D | 111.9 (5) | C01D—C11D—H04D | 107.3 |
C25D—C26D—C21D | 112.6 (4) | C12D—C11D—H04D | 107.3 |
C01A—O01A—H01A | 113 (4) | C16D—C11D—H04D | 107.3 |
C02A—O02A—H02A | 108 (4) | C11D—C12D—H05D | 109.2 |
C01B—O01B—H01B | 106 (3) | C11D—C12D—H06D | 109.2 |
C02B—O02B—H02B | 117 (3) | C13D—C12D—H05D | 109.2 |
C01C—O01C—H01C | 108 (3) | C13D—C12D—H06D | 109.2 |
C02C—O02C—H02C | 107 (4) | C12D—C13D—H07D | 109.3 |
C01D—O01D—H01D | 112 (3) | C12D—C13D—H08D | 109.3 |
C02D—O02D—H02D | 107 (5) | C14D—C13D—H07D | 109.3 |
O01A—C01A—H03A | 108.2 | C14D—C13D—H08D | 109.3 |
C02A—C01A—H03A | 108.2 | C13D—C14D—H09D | 109.6 |
C11A—C01A—H03A | 108.2 | C13D—C14D—H10D | 109.6 |
O02A—C02A—H15A | 107.0 | C15D—C14D—H09D | 109.6 |
C01A—C02A—H15A | 107.0 | C15D—C14D—H10D | 109.6 |
C21A—C02A—H15A | 107.0 | C14D—C15D—H11D | 109.2 |
C01A—C11A—H04A | 107.2 | C14D—C15D—H12D | 109.2 |
C12A—C11A—H04A | 107.2 | C16D—C15D—H11D | 109.2 |
C16A—C11A—H04A | 107.2 | C16D—C15D—H12D | 109.2 |
C11A—C12A—H05A | 109.2 | C11D—C16D—H13D | 109.2 |
C11A—C12A—H06A | 109.2 | C11D—C16D—H14D | 109.2 |
C13A—C12A—H05A | 109.2 | C15D—C16D—H13D | 109.2 |
C13A—C12A—H06A | 109.2 | C15D—C16D—H14D | 109.2 |
C12A—C13A—H07A | 109.4 | C02D—C21D—H16D | 107.3 |
C12A—C13A—H08A | 109.4 | C22D—C21D—H16D | 107.3 |
C14A—C13A—H07A | 109.4 | C26D—C21D—H16D | 107.3 |
C14A—C13A—H08A | 109.4 | C21D—C22D—H17D | 109.1 |
C13A—C14A—H09A | 109.1 | C21D—C22D—H18D | 109.1 |
C13A—C14A—H10A | 109.1 | C23D—C22D—H17D | 109.1 |
C15A—C14A—H09A | 109.1 | C23D—C22D—H18D | 109.1 |
C15A—C14A—H10A | 109.1 | C22D—C23D—H19D | 109.4 |
C14A—C15A—H11A | 109.8 | C22D—C23D—H20D | 109.4 |
C14A—C15A—H12A | 109.8 | C24D—C23D—H19D | 109.4 |
C16A—C15A—H11A | 109.8 | C24D—C23D—H20D | 109.4 |
C16A—C15A—H12A | 109.8 | C23D—C24D—H21D | 109.4 |
C11A—C16A—H13A | 108.7 | C23D—C24D—H22D | 109.4 |
C11A—C16A—H14A | 108.7 | C25D—C24D—H21D | 109.4 |
C15A—C16A—H13A | 108.7 | C25D—C24D—H22D | 109.4 |
C15A—C16A—H14A | 108.7 | C24D—C25D—H23D | 109.2 |
C02A—C21A—H16A | 108.1 | C24D—C25D—H24D | 109.2 |
C22A—C21A—H16A | 108.1 | C26D—C25D—H23D | 109.2 |
C26A—C21A—H16A | 108.1 | C26D—C25D—H24D | 109.2 |
C21A—C22A—H17A | 109.2 | C21D—C26D—H25D | 109.1 |
C21A—C22A—H18A | 109.2 | C21D—C26D—H26D | 109.1 |
C23A—C22A—H17A | 109.2 | C25D—C26D—H25D | 109.1 |
C23A—C22A—H18A | 109.2 | C25D—C26D—H26D | 109.1 |
C22A—C23A—H19A | 109.2 | H05A—C12A—H06A | 107.9 |
C22A—C23A—H20A | 109.2 | H07A—C13A—H08A | 108.0 |
C24A—C23A—H19A | 109.2 | H09A—C14A—H10A | 107.9 |
C24A—C23A—H20A | 109.2 | H11A—C15A—H12A | 108.3 |
C23A—C24A—H21A | 109.7 | H13A—C16A—H14A | 107.6 |
C23A—C24A—H22A | 109.7 | H17A—C22A—H18A | 107.9 |
C25A—C24A—H21A | 109.7 | H19A—C23A—H20A | 107.9 |
C25A—C24A—H22A | 109.7 | H21A—C24A—H22A | 108.2 |
C24A—C25A—H23A | 109.4 | H23A—C25A—H24A | 108.0 |
C24A—C25A—H24A | 109.4 | H25A—C26A—H26A | 107.7 |
C26A—C25A—H23A | 109.4 | H05B—C12B—H06B | 107.9 |
C26A—C25A—H24A | 109.4 | H07B—C13B—H08B | 107.9 |
C21A—C26A—H25A | 108.9 | H09B—C14B—H10B | 108.0 |
C21A—C26A—H26A | 108.9 | H11B—C15B—H12B | 107.9 |
C25A—C26A—H25A | 108.9 | H13B—C16B—H14B | 107.8 |
C25A—C26A—H26A | 108.9 | H17B—C22B—H18B | 107.8 |
O01B—C01B—H03B | 108.5 | H19B—C23B—H20B | 108.0 |
C02B—C01B—H03B | 108.5 | H21B—C24B—H22B | 107.8 |
C11B—C01B—H03B | 108.5 | H23B—C25B—H24B | 108.0 |
O02B—C02B—H15B | 106.0 | H25B—C26B—H26B | 107.7 |
C01B—C02B—H15B | 106.0 | H05C—C12C—H06C | 108.0 |
C21B—C02B—H15B | 106.0 | H07C—C13C—H08C | 107.9 |
C01B—C11B—H04B | 107.9 | H09C—C14C—H10C | 108.0 |
C12B—C11B—H04B | 107.9 | H11C—C15C—H12C | 108.1 |
C16B—C11B—H04B | 107.9 | H13C—C16C—H14C | 107.9 |
C11B—C12B—H05B | 109.2 | H17C—C22C—H18C | 107.8 |
C11B—C12B—H06B | 109.2 | H19C—C23C—H20C | 108.1 |
C13B—C12B—H05B | 109.2 | H21C—C24C—H22C | 108.1 |
C13B—C12B—H06B | 109.2 | H23C—C25C—H24C | 107.9 |
C12B—C13B—H07B | 109.3 | H25C—C26C—H26C | 107.9 |
C12B—C13B—H08B | 109.3 | H05D—C12D—H06D | 107.9 |
C14B—C13B—H07B | 109.3 | H07D—C13D—H08D | 108.0 |
C14B—C13B—H08B | 109.3 | H09D—C14D—H10D | 108.1 |
C13B—C14B—H09B | 109.4 | H11D—C15D—H12D | 107.9 |
C13B—C14B—H10B | 109.4 | H13D—C16D—H14D | 107.9 |
C15B—C14B—H09B | 109.4 | H17D—C22D—H18D | 107.9 |
C15B—C14B—H10B | 109.4 | H19D—C23D—H20D | 108.0 |
C14B—C15B—H11B | 109.2 | H21D—C24D—H22D | 108.0 |
C14B—C15B—H12B | 109.2 | H23D—C25D—H24D | 107.9 |
C16B—C15B—H11B | 109.2 | H25D—C26D—H26D | 107.8 |
| | | |
O01A—C01A—C11A—C16A | −165.4 (4) | O01C—C01C—C11C—C16C | −166.6 (4) |
C02A—C01A—C11A—C16A | 74.3 (5) | C02C—C01C—C11C—C16C | 73.1 (5) |
O01A—C01A—C11A—C12A | −41.0 (6) | O01C—C01C—C11C—C12C | −41.9 (5) |
C02A—C01A—C11A—C12A | −161.3 (5) | C02C—C01C—C11C—C12C | −162.2 (5) |
C16A—C11A—C12A—C13A | −53.9 (8) | C16C—C11C—C12C—C13C | −54.3 (7) |
C01A—C11A—C12A—C13A | 179.7 (6) | C01C—C11C—C12C—C13C | 179.9 (5) |
C11A—C12A—C13A—C14A | 55.6 (9) | C11C—C12C—C13C—C14C | 56.4 (8) |
C12A—C13A—C14A—C15A | −56.0 (10) | C12C—C13C—C14C—C15C | −56.9 (9) |
C13A—C14A—C15A—C16A | 54.6 (10) | C13C—C14C—C15C—C16C | 56.0 (10) |
C01A—C11A—C16A—C15A | −179.1 (5) | C12C—C11C—C16C—C15C | 54.7 (7) |
C12A—C11A—C16A—C15A | 54.6 (8) | C01C—C11C—C16C—C15C | −179.0 (5) |
C14A—C15A—C16A—C11A | −54.9 (10) | C14C—C15C—C16C—C11C | −55.5 (9) |
O01A—C01A—C02A—O02A | −65.4 (4) | O01C—C01C—C02C—O02C | −64.3 (4) |
C11A—C01A—C02A—O02A | 58.5 (5) | C11C—C01C—C02C—O02C | 59.0 (5) |
O01A—C01A—C02A—C21A | 61.6 (4) | O01C—C01C—C02C—C21C | 62.3 (4) |
C11A—C01A—C02A—C21A | −174.5 (4) | C11C—C01C—C02C—C21C | −174.4 (4) |
O02A—C02A—C21A—C26A | −161.7 (4) | O02C—C02C—C21C—C22C | −39.5 (5) |
C01A—C02A—C21A—C26A | 73.8 (5) | C01C—C02C—C21C—C22C | −164.2 (4) |
O02A—C02A—C21A—C22A | −39.3 (5) | O02C—C02C—C21C—C26C | −162.7 (3) |
C01A—C02A—C21A—C22A | −163.8 (4) | C01C—C02C—C21C—C26C | 72.5 (4) |
C02A—C21A—C22A—C23A | −177.8 (4) | C26C—C21C—C22C—C23C | −54.9 (6) |
C26A—C21A—C22A—C23A | −54.1 (6) | C02C—C21C—C22C—C23C | −178.5 (4) |
C21A—C22A—C23A—C24A | 58.0 (6) | C21C—C22C—C23C—C24C | 57.2 (6) |
C22A—C23A—C24A—C25A | −57.0 (6) | C22C—C23C—C24C—C25C | −56.2 (6) |
C23A—C24A—C25A—C26A | 54.9 (7) | C23C—C24C—C25C—C26C | 55.4 (7) |
C24A—C25A—C26A—C21A | −54.6 (7) | C24C—C25C—C26C—C21C | −54.2 (6) |
C02A—C21A—C26A—C25A | 177.8 (4) | C22C—C21C—C26C—C25C | 53.2 (5) |
C22A—C21A—C26A—C25A | 53.4 (6) | C02C—C21C—C26C—C25C | 177.9 (4) |
O01B—C01B—C11B—C12B | −47.8 (5) | O01D—C01D—C11D—C16D | −172.4 (4) |
C02B—C01B—C11B—C12B | −168.0 (4) | C02D—C01D—C11D—C16D | 67.5 (5) |
O01B—C01B—C11B—C16B | −170.4 (4) | O01D—C01D—C11D—C12D | −48.0 (5) |
C02B—C01B—C11B—C16B | 69.3 (5) | C02D—C01D—C11D—C12D | −168.1 (4) |
C16B—C11B—C12B—C13B | −56.1 (6) | C16D—C11D—C12D—C13D | −55.4 (6) |
C01B—C11B—C12B—C13B | 179.6 (4) | C01D—C11D—C12D—C13D | 178.7 (4) |
C11B—C12B—C13B—C14B | 57.4 (7) | C11D—C12D—C13D—C14D | 56.7 (6) |
C12B—C13B—C14B—C15B | −54.2 (7) | C12D—C13D—C14D—C15D | −55.3 (7) |
C13B—C14B—C15B—C16B | 52.0 (8) | C13D—C14D—C15D—C16D | 54.5 (7) |
C12B—C11B—C16B—C15B | 54.0 (6) | C12D—C11D—C16D—C15D | 54.4 (6) |
C01B—C11B—C16B—C15B | 178.6 (4) | C01D—C11D—C16D—C15D | −179.5 (4) |
C14B—C15B—C16B—C11B | −53.2 (7) | C14D—C15D—C16D—C11D | −55.1 (7) |
O01B—C01B—C02B—O02B | −67.0 (4) | O01D—C01D—C02D—O02D | −67.5 (4) |
C11B—C01B—C02B—O02B | 55.4 (5) | C11D—C01D—C02D—O02D | 54.7 (5) |
O01B—C01B—C02B—C21B | 61.4 (5) | O01D—C01D—C02D—C21D | 60.4 (5) |
C11B—C01B—C02B—C21B | −176.1 (4) | C11D—C01D—C02D—C21D | −177.4 (4) |
O02B—C02B—C21B—C22B | 48.2 (5) | O02D—C02D—C21D—C22D | 50.6 (5) |
C01B—C02B—C21B—C22B | −79.8 (5) | C01D—C02D—C21D—C22D | −77.2 (5) |
O02B—C02B—C21B—C26B | −75.8 (5) | O02D—C02D—C21D—C26D | −73.3 (5) |
C01B—C02B—C21B—C26B | 156.2 (4) | C01D—C02D—C21D—C26D | 158.9 (4) |
C02B—C21B—C22B—C23B | −178.1 (4) | C02D—C21D—C22D—C23D | −178.7 (4) |
C26B—C21B—C22B—C23B | −53.5 (6) | C26D—C21D—C22D—C23D | −54.4 (6) |
C21B—C22B—C23B—C24B | 55.1 (8) | C21D—C22D—C23D—C24D | 56.4 (7) |
C22B—C23B—C24B—C25B | −55.1 (9) | C22D—C23D—C24D—C25D | −55.6 (8) |
C23B—C24B—C25B—C26B | 54.2 (8) | C23D—C24D—C25D—C26D | 55.1 (7) |
C24B—C25B—C26B—C21B | −53.9 (7) | C24D—C25D—C26D—C21D | −55.0 (6) |
C02B—C21B—C26B—C25B | −179.9 (5) | C22D—C21D—C26D—C25D | 53.7 (6) |
C22B—C21B—C26B—C25B | 52.7 (6) | C02D—C21D—C26D—C25D | −178.8 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O01A—H01A···O02Ai | 1.01 (8) | 1.76 (8) | 2.760 (4) | 174 (6) |
O01B—H01B···O02Bii | 0.73 (4) | 1.98 (5) | 2.704 (4) | 168 (4) |
O01C—H01C···O02Ci | 0.82 (5) | 1.95 (5) | 2.759 (4) | 167 (4) |
O01D—H01D···O02Dii | 0.83 (5) | 1.86 (5) | 2.682 (4) | 176 (5) |
O02A—H02A···O01B | 0.79 (6) | 1.95 (6) | 2.717 (5) | 163 (6) |
O02B—H02B···O01A | 0.81 (5) | 1.98 (5) | 2.746 (5) | 158 (4) |
O02C—H02C···O01D | 0.87 (6) | 1.90 (6) | 2.725 (5) | 158 (5) |
O02D—H02D···O01C | 0.72 (6) | 2.15 (6) | 2.731 (5) | 140 (6) |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
(k00009)
S,
S-1,2-dicyclohexylethane-1,2-diol
top
Crystal data top
C14H26O2 | Dx = 1.112 Mg m−3 |
Mr = 226.35 | Melting point: 130-135 C K |
Monoclinic, P1211 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.4816 (6) Å | Cell parameters from 39527 reflections |
b = 41.262 (6) Å | θ = 1.0–25.0° |
c = 11.954 (2) Å | µ = 0.07 mm−1 |
β = 90.39 (1)° | T = 173 K |
V = 2703.7 (7) Å3 | Needles. Long axis is a. Prism faces are {010} and {001}., colourless |
Z = 8 | 0.44 × 0.20 × 0.16 mm |
F(000) = 1008 | |
Data collection top
Nonius Kappa-CCD diffractometer | 3750 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.034 |
Graphite monochromator | θmax = 25.0°, θmin = 1.7° |
Detector resolution: 18 pixels mm-1 | h = −6→6 |
ϕ and ω scans with 0.4° steps | k = −48→48 |
8305 measured reflections | l = −14→14 |
4720 independent reflections | |
Refinement top
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)] = 0.042 | Hydrogen site location: mixed |
wR(F2) = 0.089 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.042)2] where P = (Fo2 + 2Fc2)/3 |
4720 reflections | (Δ/σ)max < 0.001 |
609 parameters | Δρmax = 0.12 e Å−3 |
1 restraint | Δρmin = −0.15 e Å−3 |
Crystal data top
C14H26O2 | V = 2703.7 (7) Å3 |
Mr = 226.35 | Z = 8 |
Monoclinic, P1211 | Mo Kα radiation |
a = 5.4816 (6) Å | µ = 0.07 mm−1 |
b = 41.262 (6) Å | T = 173 K |
c = 11.954 (2) Å | 0.44 × 0.20 × 0.16 mm |
β = 90.39 (1)° | |
Data collection top
Nonius Kappa-CCD diffractometer | 3750 reflections with I > 2σ(I) |
8305 measured reflections | Rint = 0.034 |
4720 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.042 | 1 restraint |
wR(F2) = 0.089 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.12 e Å−3 |
4720 reflections | Δρmin = −0.15 e Å−3 |
609 parameters | |
Special details top
Experimental. The crystal-to-detector distance was 50 mm. Each frame was measured for 36 s. The number of scan sets measured was 4; the total number of frames measured was 1135. |
Refinement. Friedel reflections were merged during the refinement. The hydroxyl H atoms were located in difference maps and refined isotropically. All other H atoms were placed in calculated positions. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O01A | 0.5367 (3) | 0.09732 (5) | 0.61880 (14) | 0.0290 (5) | |
H01A | 0.698 (7) | 0.0979 (11) | 0.605 (3) | 0.098 (15)* | |
O02A | 0.0316 (3) | 0.10083 (5) | 0.60349 (14) | 0.0271 (5) | |
H02A | 0.097 (8) | 0.0804 (12) | 0.647 (4) | 0.124 (16)* | |
C01A | 0.4222 (4) | 0.12622 (7) | 0.57755 (19) | 0.0240 (6) | |
H03A | 0.5231 | 0.1453 | 0.6010 | 0.029* | |
C11A | 0.4026 (5) | 0.12607 (7) | 0.4502 (2) | 0.0266 (7) | |
H04A | 0.2677 | 0.1109 | 0.4290 | 0.032* | |
C12A | 0.6336 (5) | 0.11418 (9) | 0.3936 (2) | 0.0395 (8) | |
H05A | 0.7720 | 0.1282 | 0.4164 | 0.047* | |
H06A | 0.6696 | 0.0919 | 0.4190 | 0.047* | |
C13A | 0.6114 (6) | 0.11443 (10) | 0.2668 (2) | 0.0565 (11) | |
H07A | 0.7687 | 0.1077 | 0.2339 | 0.068* | |
H08A | 0.4857 | 0.0986 | 0.2433 | 0.068* | |
C14A | 0.5435 (6) | 0.14741 (11) | 0.2226 (2) | 0.0575 (10) | |
H09A | 0.5179 | 0.1462 | 0.1407 | 0.069* | |
H10A | 0.6789 | 0.1628 | 0.2373 | 0.069* | |
C15A | 0.3133 (6) | 0.15978 (11) | 0.2776 (2) | 0.0633 (11) | |
H11A | 0.1736 | 0.1461 | 0.2544 | 0.076* | |
H12A | 0.2805 | 0.1822 | 0.2521 | 0.076* | |
C16A | 0.3369 (6) | 0.15934 (8) | 0.4052 (2) | 0.0430 (9) | |
H13A | 0.4640 | 0.1750 | 0.4285 | 0.052* | |
H14A | 0.1804 | 0.1663 | 0.4383 | 0.052* | |
C02A | 0.1735 (4) | 0.12828 (7) | 0.6364 (2) | 0.0241 (6) | |
H15A | 0.0884 | 0.1480 | 0.6073 | 0.029* | |
C21A | 0.1938 (5) | 0.13185 (7) | 0.76393 (19) | 0.0244 (6) | |
H16A | 0.3213 | 0.1164 | 0.7915 | 0.029* | |
C22A | −0.0466 (5) | 0.12368 (8) | 0.8221 (2) | 0.0329 (7) | |
H17A | −0.1776 | 0.1378 | 0.7920 | 0.040* | |
H18A | −0.0911 | 0.1009 | 0.8056 | 0.040* | |
C23A | −0.0283 (6) | 0.12826 (8) | 0.9487 (2) | 0.0422 (8) | |
H19A | −0.1882 | 0.1235 | 0.9830 | 0.051* | |
H20A | 0.0928 | 0.1129 | 0.9799 | 0.051* | |
C24A | 0.0474 (5) | 0.16270 (8) | 0.9774 (2) | 0.0395 (8) | |
H21A | 0.0653 | 0.1649 | 1.0595 | 0.047* | |
H22A | −0.0812 | 0.1779 | 0.9522 | 0.047* | |
C25A | 0.2877 (5) | 0.17135 (9) | 0.9214 (2) | 0.0451 (9) | |
H23A | 0.4199 | 0.1578 | 0.9532 | 0.054* | |
H24A | 0.3275 | 0.1943 | 0.9371 | 0.054* | |
C26A | 0.2734 (5) | 0.16611 (8) | 0.7950 (2) | 0.0353 (7) | |
H25A | 0.1565 | 0.1818 | 0.7623 | 0.042* | |
H26A | 0.4355 | 0.1704 | 0.7622 | 0.042* | |
O01B | 0.1087 (3) | 0.04393 (5) | 0.70628 (14) | 0.0295 (5) | |
H01B | −0.060 (6) | 0.0394 (8) | 0.705 (2) | 0.049 (9)* | |
O02B | 0.6265 (3) | 0.03820 (5) | 0.71241 (15) | 0.0333 (5) | |
H02B | 0.541 (6) | 0.0576 (9) | 0.694 (2) | 0.058 (11)* | |
C01B | 0.2296 (4) | 0.01427 (7) | 0.6770 (2) | 0.0257 (6) | |
H03B | 0.1234 | −0.0043 | 0.6999 | 0.031* | |
C11B | 0.2677 (5) | 0.01235 (7) | 0.5494 (2) | 0.0271 (7) | |
H04B | 0.3944 | 0.0287 | 0.5293 | 0.033* | |
C12B | 0.0359 (5) | 0.02062 (8) | 0.4839 (2) | 0.0379 (8) | |
H05B | −0.0944 | 0.0051 | 0.5042 | 0.046* | |
H06B | −0.0193 | 0.0426 | 0.5049 | 0.046* | |
C13B | 0.0765 (6) | 0.01932 (9) | 0.3586 (2) | 0.0439 (9) | |
H07B | −0.0786 | 0.0242 | 0.3192 | 0.053* | |
H08B | 0.1972 | 0.0360 | 0.3374 | 0.053* | |
C14B | 0.1672 (5) | −0.01355 (8) | 0.3226 (2) | 0.0432 (8) | |
H09B | 0.2019 | −0.0132 | 0.2414 | 0.052* | |
H10B | 0.0390 | −0.0300 | 0.3360 | 0.052* | |
C15B | 0.3966 (6) | −0.02279 (9) | 0.3865 (2) | 0.0450 (9) | |
H11B | 0.5313 | −0.0082 | 0.3643 | 0.054* | |
H12B | 0.4436 | −0.0452 | 0.3665 | 0.054* | |
C16B | 0.3605 (5) | −0.02058 (8) | 0.5132 (2) | 0.0378 (8) | |
H13B | 0.2428 | −0.0374 | 0.5367 | 0.045* | |
H14B | 0.5178 | −0.0250 | 0.5514 | 0.045* | |
C02B | 0.4650 (4) | 0.01269 (7) | 0.7451 (2) | 0.0270 (6) | |
H15B | 0.5468 | −0.0081 | 0.7241 | 0.032* | |
C21B | 0.4359 (5) | 0.01198 (7) | 0.8730 (2) | 0.0290 (7) | |
H16B | 0.2976 | −0.0030 | 0.8901 | 0.035* | |
C22B | 0.3780 (6) | 0.04459 (8) | 0.9265 (2) | 0.0404 (8) | |
H17B | 0.5072 | 0.0603 | 0.9068 | 0.048* | |
H18B | 0.2217 | 0.0528 | 0.8956 | 0.048* | |
C23B | 0.3594 (6) | 0.04245 (9) | 1.0530 (2) | 0.0501 (9) | |
H19B | 0.3289 | 0.0643 | 1.0839 | 0.060* | |
H20B | 0.2195 | 0.0285 | 1.0729 | 0.060* | |
C24B | 0.5908 (6) | 0.02871 (9) | 1.1051 (2) | 0.0480 (9) | |
H21B | 0.7282 | 0.0438 | 1.0919 | 0.058* | |
H22B | 0.5694 | 0.0265 | 1.1869 | 0.058* | |
C25B | 0.6498 (6) | −0.00405 (9) | 1.0553 (2) | 0.0445 (8) | |
H23B | 0.5219 | −0.0198 | 1.0765 | 0.053* | |
H24B | 0.8073 | −0.0118 | 1.0861 | 0.053* | |
C26B | 0.6656 (5) | −0.00222 (8) | 0.9277 (2) | 0.0374 (8) | |
H25B | 0.6932 | −0.0243 | 0.8978 | 0.045* | |
H26B | 0.8077 | 0.0113 | 0.9072 | 0.045* | |
O01C | 1.0372 (3) | 0.30285 (5) | 0.95418 (14) | 0.0297 (5) | |
H01C | 1.205 (7) | 0.3004 (9) | 0.964 (3) | 0.076 (12)* | |
O02C | 0.5340 (3) | 0.29977 (5) | 0.96792 (14) | 0.0277 (5) | |
H02C | 0.605 (6) | 0.3190 (10) | 0.936 (3) | 0.075 (12)* | |
C01C | 0.9234 (4) | 0.27381 (7) | 0.9935 (2) | 0.0233 (6) | |
H03C | 1.0235 | 0.2548 | 0.9695 | 0.028* | |
C11C | 0.9055 (5) | 0.27356 (7) | 1.1210 (2) | 0.0278 (7) | |
H04C | 0.7724 | 0.2889 | 1.1426 | 0.033* | |
C12C | 1.1399 (5) | 0.28485 (9) | 1.1785 (2) | 0.0423 (9) | |
H05C | 1.2763 | 0.2707 | 1.1554 | 0.051* | |
H06C | 1.1779 | 0.3072 | 1.1540 | 0.051* | |
C13C | 1.1187 (6) | 0.28416 (10) | 1.3054 (2) | 0.0548 (10) | |
H07C | 1.2770 | 0.2906 | 1.3391 | 0.066* | |
H08C | 0.9949 | 0.3002 | 1.3290 | 0.066* | |
C14C | 1.0484 (6) | 0.25133 (11) | 1.3483 (2) | 0.0582 (11) | |
H09C | 1.0243 | 0.2524 | 1.4303 | 0.070* | |
H10C | 1.1817 | 0.2358 | 1.3335 | 0.070* | |
C15C | 0.8160 (6) | 0.23957 (10) | 1.2925 (2) | 0.0560 (10) | |
H11C | 0.6782 | 0.2535 | 1.3156 | 0.067* | |
H12C | 0.7809 | 0.2172 | 1.3173 | 0.067* | |
C16C | 0.8379 (6) | 0.24026 (8) | 1.1643 (2) | 0.0434 (8) | |
H13C | 0.9637 | 0.2245 | 1.1409 | 0.052* | |
H14C | 0.6806 | 0.2336 | 1.1304 | 0.052* | |
C02C | 0.6746 (4) | 0.27211 (7) | 0.9345 (2) | 0.0254 (7) | |
H15C | 0.5891 | 0.2524 | 0.9630 | 0.031* | |
C21C | 0.6907 (4) | 0.26888 (7) | 0.8071 (2) | 0.0251 (7) | |
H16C | 0.8170 | 0.2845 | 0.7802 | 0.030* | |
C22C | 0.4498 (5) | 0.27702 (8) | 0.7482 (2) | 0.0336 (7) | |
H17C | 0.3192 | 0.2630 | 0.7781 | 0.040* | |
H18C | 0.4057 | 0.2998 | 0.7645 | 0.040* | |
C23C | 0.4657 (6) | 0.27238 (8) | 0.6221 (2) | 0.0409 (8) | |
H19C | 0.3046 | 0.2770 | 0.5877 | 0.049* | |
H20C | 0.5847 | 0.2880 | 0.5912 | 0.049* | |
C24C | 0.5427 (5) | 0.23845 (8) | 0.5919 (2) | 0.0421 (8) | |
H21C | 0.5601 | 0.2367 | 0.5098 | 0.051* | |
H22C | 0.4157 | 0.2229 | 0.6158 | 0.051* | |
C25C | 0.7833 (5) | 0.23002 (9) | 0.6483 (2) | 0.0437 (9) | |
H23C | 0.9138 | 0.2439 | 0.6174 | 0.052* | |
H24C | 0.8248 | 0.2072 | 0.6317 | 0.052* | |
C26C | 0.7724 (5) | 0.23472 (8) | 0.7748 (2) | 0.0345 (7) | |
H25C | 0.9357 | 0.2305 | 0.8075 | 0.041* | |
H26C | 0.6575 | 0.2188 | 0.8068 | 0.041* | |
O01D | 0.6123 (4) | 0.35660 (5) | 0.86249 (14) | 0.0284 (5) | |
H01D | 0.459 (5) | 0.3591 (8) | 0.858 (2) | 0.041 (9)* | |
O02D | 1.1288 (3) | 0.36160 (5) | 0.86081 (15) | 0.0321 (5) | |
H02D | 1.048 (8) | 0.3438 (12) | 0.885 (3) | 0.104 (16)* | |
C01D | 0.7342 (4) | 0.38636 (7) | 0.8911 (2) | 0.0254 (7) | |
H03D | 0.6291 | 0.4049 | 0.8668 | 0.030* | |
C11D | 0.7732 (5) | 0.38854 (7) | 1.0183 (2) | 0.0295 (7) | |
H04D | 0.8981 | 0.3720 | 1.0396 | 0.035* | |
C12D | 0.5396 (5) | 0.38080 (8) | 1.0827 (2) | 0.0389 (8) | |
H05D | 0.4800 | 0.3590 | 1.0610 | 0.047* | |
H06D | 0.4118 | 0.3968 | 1.0628 | 0.047* | |
C13D | 0.5856 (5) | 0.38170 (8) | 1.2097 (2) | 0.0422 (8) | |
H07D | 0.4313 | 0.3772 | 1.2494 | 0.051* | |
H08D | 0.7044 | 0.3646 | 1.2305 | 0.051* | |
C14D | 0.6836 (5) | 0.41449 (9) | 1.2459 (2) | 0.0443 (8) | |
H09D | 0.7208 | 0.4141 | 1.3270 | 0.053* | |
H10D | 0.5582 | 0.4313 | 1.2322 | 0.053* | |
C15D | 0.9133 (6) | 0.42280 (9) | 1.1814 (2) | 0.0447 (9) | |
H11D | 1.0443 | 0.4073 | 1.2019 | 0.054* | |
H12D | 0.9685 | 0.4448 | 1.2025 | 0.054* | |
C16D | 0.8696 (5) | 0.42148 (8) | 1.0547 (2) | 0.0372 (8) | |
H13D | 0.7507 | 0.4385 | 1.0331 | 0.045* | |
H14D | 1.0245 | 0.4260 | 1.0156 | 0.045* | |
C02D | 0.9699 (4) | 0.38720 (7) | 0.8242 (2) | 0.0266 (7) | |
H15D | 1.0534 | 0.4080 | 0.8443 | 0.032* | |
C21D | 0.9452 (5) | 0.38698 (7) | 0.6965 (2) | 0.0292 (7) | |
H16D | 0.8147 | 0.4029 | 0.6760 | 0.035* | |
C22D | 0.8760 (5) | 0.35457 (8) | 0.6436 (2) | 0.0383 (8) | |
H17D | 0.7153 | 0.3476 | 0.6725 | 0.046* | |
H18D | 0.9977 | 0.3380 | 0.6660 | 0.046* | |
C23D | 0.8637 (5) | 0.35637 (9) | 0.5160 (2) | 0.0464 (9) | |
H19D | 0.8258 | 0.3346 | 0.4855 | 0.056* | |
H20D | 0.7306 | 0.3712 | 0.4933 | 0.056* | |
C24D | 1.1040 (5) | 0.36833 (9) | 0.4673 (2) | 0.0460 (9) | |
H21D | 1.2345 | 0.3524 | 0.4833 | 0.055* | |
H22D | 1.0878 | 0.3705 | 0.3851 | 0.055* | |
C25D | 1.1722 (5) | 0.40077 (8) | 0.5176 (2) | 0.0430 (8) | |
H23D | 1.0500 | 0.4172 | 0.4948 | 0.052* | |
H24D | 1.3328 | 0.4076 | 0.4885 | 0.052* | |
C26D | 1.1841 (5) | 0.39901 (8) | 0.6444 (2) | 0.0336 (7) | |
H25D | 1.2224 | 0.4208 | 0.6743 | 0.040* | |
H26D | 1.3183 | 0.3843 | 0.6667 | 0.040* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O01A | 0.0209 (11) | 0.0322 (13) | 0.0339 (12) | 0.0032 (9) | 0.0024 (8) | 0.0083 (9) |
O02A | 0.0198 (10) | 0.0325 (13) | 0.0289 (11) | −0.0018 (9) | −0.0002 (7) | 0.0002 (9) |
C01A | 0.0206 (14) | 0.0267 (18) | 0.0246 (15) | −0.0001 (13) | −0.0004 (11) | 0.0013 (12) |
C11A | 0.0232 (15) | 0.0314 (19) | 0.0252 (15) | 0.0003 (13) | −0.0010 (11) | −0.0014 (13) |
C12A | 0.0385 (17) | 0.056 (2) | 0.0245 (16) | 0.0142 (16) | 0.0026 (12) | −0.0008 (15) |
C13A | 0.053 (2) | 0.086 (3) | 0.0302 (19) | 0.014 (2) | 0.0072 (15) | −0.0118 (19) |
C14A | 0.057 (2) | 0.093 (3) | 0.0224 (18) | 0.011 (2) | 0.0068 (15) | 0.0098 (19) |
C15A | 0.070 (2) | 0.092 (3) | 0.0279 (18) | 0.032 (2) | 0.0058 (16) | 0.0165 (19) |
C16A | 0.054 (2) | 0.049 (2) | 0.0264 (17) | 0.0200 (17) | 0.0087 (14) | 0.0080 (15) |
C02A | 0.0208 (14) | 0.0243 (18) | 0.0273 (15) | 0.0013 (13) | −0.0016 (11) | 0.0006 (12) |
C21A | 0.0214 (14) | 0.0282 (18) | 0.0236 (15) | 0.0060 (13) | 0.0011 (11) | 0.0029 (12) |
C22A | 0.0320 (16) | 0.038 (2) | 0.0292 (16) | −0.0030 (14) | 0.0058 (12) | −0.0005 (13) |
C23A | 0.0467 (19) | 0.048 (2) | 0.0322 (18) | 0.0052 (17) | 0.0099 (14) | 0.0057 (15) |
C24A | 0.0464 (19) | 0.052 (2) | 0.0205 (16) | 0.0053 (16) | 0.0018 (13) | −0.0032 (14) |
C25A | 0.049 (2) | 0.054 (2) | 0.0323 (18) | −0.0031 (18) | −0.0013 (14) | −0.0112 (16) |
C26A | 0.0347 (17) | 0.040 (2) | 0.0314 (17) | −0.0024 (15) | 0.0049 (12) | −0.0054 (14) |
O01B | 0.0195 (11) | 0.0316 (13) | 0.0374 (12) | 0.0004 (10) | −0.0033 (8) | −0.0005 (9) |
O02B | 0.0190 (10) | 0.0362 (14) | 0.0447 (13) | −0.0019 (10) | −0.0012 (8) | 0.0130 (10) |
C01B | 0.0204 (14) | 0.0235 (18) | 0.0333 (16) | 0.0031 (14) | 0.0022 (11) | 0.0029 (13) |
C11B | 0.0260 (15) | 0.0274 (18) | 0.0280 (16) | −0.0041 (14) | −0.0015 (11) | 0.0032 (12) |
C12B | 0.0351 (17) | 0.049 (2) | 0.0292 (17) | 0.0086 (16) | −0.0095 (12) | −0.0027 (14) |
C13B | 0.0397 (18) | 0.055 (3) | 0.0367 (19) | 0.0051 (17) | −0.0115 (14) | −0.0025 (16) |
C14B | 0.046 (2) | 0.054 (2) | 0.0295 (18) | −0.0016 (18) | −0.0033 (13) | −0.0055 (15) |
C15B | 0.047 (2) | 0.051 (2) | 0.0374 (19) | 0.0115 (18) | 0.0007 (14) | −0.0096 (16) |
C16B | 0.0365 (17) | 0.040 (2) | 0.0365 (18) | 0.0066 (16) | −0.0027 (13) | 0.0002 (15) |
C02B | 0.0224 (15) | 0.0238 (17) | 0.0347 (16) | 0.0014 (13) | −0.0007 (12) | 0.0042 (13) |
C21B | 0.0239 (14) | 0.0334 (19) | 0.0297 (16) | 0.0001 (14) | −0.0019 (12) | 0.0051 (13) |
C22B | 0.0415 (18) | 0.043 (2) | 0.0361 (19) | 0.0093 (16) | −0.0100 (13) | −0.0054 (15) |
C23B | 0.051 (2) | 0.064 (3) | 0.0356 (19) | 0.0119 (19) | −0.0118 (15) | −0.0115 (16) |
C24B | 0.046 (2) | 0.064 (3) | 0.0339 (18) | 0.0041 (18) | −0.0094 (14) | 0.0010 (17) |
C25B | 0.0424 (18) | 0.056 (2) | 0.0348 (19) | 0.0055 (17) | −0.0130 (13) | 0.0048 (16) |
C26B | 0.0344 (17) | 0.043 (2) | 0.0343 (18) | 0.0065 (16) | −0.0096 (13) | 0.0042 (14) |
O01C | 0.0195 (11) | 0.0355 (13) | 0.0341 (12) | −0.0025 (10) | −0.0021 (8) | 0.0086 (9) |
O02C | 0.0187 (10) | 0.0321 (13) | 0.0322 (12) | 0.0009 (10) | 0.0019 (8) | −0.0008 (9) |
C01C | 0.0197 (14) | 0.0275 (18) | 0.0228 (15) | −0.0012 (13) | 0.0031 (11) | −0.0002 (12) |
C11C | 0.0258 (15) | 0.036 (2) | 0.0221 (15) | −0.0011 (14) | 0.0014 (11) | 0.0002 (13) |
C12C | 0.0400 (18) | 0.059 (2) | 0.0282 (18) | −0.0124 (17) | −0.0048 (13) | −0.0007 (15) |
C13C | 0.052 (2) | 0.081 (3) | 0.031 (2) | −0.013 (2) | −0.0093 (15) | −0.0097 (18) |
C14C | 0.059 (2) | 0.091 (3) | 0.0246 (18) | −0.014 (2) | −0.0083 (15) | 0.0058 (18) |
C15C | 0.061 (2) | 0.078 (3) | 0.0280 (18) | −0.027 (2) | −0.0066 (15) | 0.0168 (17) |
C16C | 0.057 (2) | 0.048 (2) | 0.0249 (16) | −0.0181 (18) | −0.0118 (14) | 0.0071 (15) |
C02C | 0.0240 (15) | 0.0272 (18) | 0.0250 (15) | 0.0003 (13) | 0.0025 (11) | −0.0005 (12) |
C21C | 0.0229 (15) | 0.0286 (18) | 0.0237 (15) | −0.0065 (13) | −0.0016 (11) | 0.0007 (12) |
C22C | 0.0338 (16) | 0.038 (2) | 0.0294 (17) | −0.0009 (15) | −0.0047 (12) | −0.0007 (13) |
C23C | 0.0465 (19) | 0.046 (2) | 0.0295 (17) | −0.0074 (17) | −0.0097 (13) | 0.0030 (15) |
C24C | 0.0455 (19) | 0.053 (2) | 0.0279 (17) | −0.0108 (17) | −0.0038 (14) | −0.0040 (15) |
C25C | 0.0446 (19) | 0.054 (2) | 0.0328 (18) | 0.0055 (17) | −0.0033 (14) | −0.0129 (15) |
C26C | 0.0344 (17) | 0.040 (2) | 0.0294 (17) | −0.0015 (15) | −0.0029 (12) | −0.0045 (14) |
O01D | 0.0184 (11) | 0.0331 (13) | 0.0337 (11) | −0.0027 (10) | 0.0014 (8) | −0.0044 (9) |
O02D | 0.0214 (10) | 0.0343 (14) | 0.0406 (12) | 0.0023 (10) | 0.0012 (8) | 0.0080 (10) |
C01D | 0.0227 (15) | 0.0238 (18) | 0.0297 (17) | 0.0025 (13) | 0.0004 (11) | −0.0018 (12) |
C11D | 0.0272 (15) | 0.0308 (19) | 0.0306 (16) | 0.0036 (14) | 0.0008 (12) | −0.0030 (13) |
C12D | 0.0329 (16) | 0.049 (2) | 0.0350 (18) | −0.0050 (16) | 0.0046 (13) | −0.0060 (15) |
C13D | 0.0430 (18) | 0.053 (2) | 0.0306 (18) | −0.0034 (18) | 0.0098 (13) | −0.0076 (15) |
C14D | 0.046 (2) | 0.052 (2) | 0.0347 (18) | 0.0098 (18) | −0.0029 (14) | −0.0114 (16) |
C15D | 0.049 (2) | 0.044 (2) | 0.0406 (19) | −0.0086 (17) | 0.0007 (15) | −0.0136 (16) |
C16D | 0.0387 (17) | 0.035 (2) | 0.0379 (18) | −0.0049 (16) | 0.0040 (13) | −0.0074 (15) |
C02D | 0.0203 (14) | 0.0264 (17) | 0.0330 (16) | 0.0005 (13) | 0.0003 (11) | 0.0010 (13) |
C21D | 0.0226 (14) | 0.0330 (19) | 0.0321 (17) | 0.0009 (14) | 0.0004 (11) | 0.0046 (13) |
C22D | 0.0402 (17) | 0.044 (2) | 0.0311 (17) | −0.0101 (16) | 0.0059 (13) | −0.0053 (14) |
C23D | 0.047 (2) | 0.060 (3) | 0.0324 (18) | −0.0101 (19) | 0.0064 (14) | −0.0063 (16) |
C24D | 0.0457 (19) | 0.063 (3) | 0.0291 (17) | −0.0015 (18) | 0.0103 (13) | 0.0032 (16) |
C25D | 0.0364 (18) | 0.049 (2) | 0.0437 (19) | 0.0005 (16) | 0.0129 (14) | 0.0129 (16) |
C26D | 0.0312 (17) | 0.0319 (19) | 0.0379 (17) | −0.0037 (14) | 0.0067 (13) | 0.0045 (14) |
Geometric parameters (Å, º) top
O01A—C01A | 1.433 (3) | C15A—H12A | 0.99 |
O02A—C02A | 1.428 (3) | C16A—H13A | 0.99 |
C01A—C02A | 1.541 (3) | C16A—H14A | 0.99 |
C01A—C11A | 1.525 (3) | C21A—H16A | 1.00 |
C02A—C21A | 1.534 (3) | C22A—H17A | 0.99 |
C11A—C12A | 1.521 (3) | C22A—H18A | 0.99 |
C11A—C16A | 1.517 (4) | C23A—H19A | 0.99 |
C12A—C13A | 1.520 (4) | C23A—H20A | 0.99 |
C13A—C14A | 1.505 (5) | C24A—H21A | 0.99 |
C14A—C15A | 1.515 (4) | C24A—H22A | 0.99 |
C15A—C16A | 1.530 (4) | C25A—H23A | 0.99 |
C21A—C22A | 1.532 (3) | C25A—H24A | 0.99 |
C21A—C26A | 1.525 (4) | C26A—H25A | 0.99 |
C22A—C23A | 1.527 (3) | C26A—H26A | 0.99 |
C23A—C24A | 1.519 (5) | C01B—H03B | 1.00 |
C24A—C25A | 1.524 (4) | C02B—H15B | 1.00 |
C25A—C26A | 1.528 (3) | C11B—H04B | 1.00 |
O01B—C01B | 1.436 (3) | C12B—H05B | 0.99 |
O02B—C02B | 1.431 (3) | C12B—H06B | 0.99 |
C01B—C02B | 1.522 (3) | C13B—H07B | 0.99 |
C01B—C11B | 1.543 (3) | C13B—H08B | 0.99 |
C02B—C21B | 1.539 (3) | C14B—H09B | 0.99 |
C11B—C12B | 1.526 (4) | C14B—H10B | 0.99 |
C11B—C16B | 1.515 (4) | C15B—H11B | 0.99 |
C12B—C13B | 1.516 (4) | C15B—H12B | 0.99 |
C13B—C14B | 1.508 (5) | C16B—H13B | 0.99 |
C14B—C15B | 1.516 (4) | C16B—H14B | 0.99 |
C15B—C16B | 1.532 (4) | C21B—H16B | 1.00 |
C21B—C22B | 1.524 (4) | C22B—H17B | 0.99 |
C21B—C26B | 1.531 (4) | C22B—H18B | 0.99 |
C22B—C23B | 1.519 (4) | C23B—H19B | 0.99 |
C23B—C24B | 1.519 (4) | C23B—H20B | 0.99 |
C24B—C25B | 1.513 (5) | C24B—H21B | 0.99 |
C25B—C26B | 1.530 (4) | C24B—H22B | 0.99 |
O01C—C01C | 1.432 (3) | C25B—H23B | 0.99 |
O02C—C02C | 1.435 (3) | C25B—H24B | 0.99 |
C01C—C02C | 1.532 (3) | C26B—H25B | 0.99 |
C01C—C11C | 1.529 (3) | C26B—H26B | 0.99 |
C02C—C21C | 1.532 (3) | C01C—H03C | 1.00 |
C11C—C12C | 1.526 (4) | C02C—H15C | 1.00 |
C11C—C16C | 1.515 (4) | C11C—H04C | 1.00 |
C12C—C13C | 1.523 (4) | C12C—H05C | 0.99 |
C13C—C14C | 1.500 (5) | C12C—H06C | 0.99 |
C14C—C15C | 1.514 (4) | C13C—H07C | 0.99 |
C15C—C16C | 1.539 (4) | C13C—H08C | 0.99 |
C21C—C22C | 1.530 (4) | C14C—H09C | 0.99 |
C21C—C26C | 1.530 (4) | C14C—H10C | 0.99 |
C22C—C23C | 1.523 (3) | C15C—H11C | 0.99 |
C23C—C24C | 1.507 (5) | C15C—H12C | 0.99 |
C24C—C25C | 1.517 (4) | C16C—H13C | 0.99 |
C25C—C26C | 1.526 (4) | C16C—H14C | 0.99 |
O01D—C01D | 1.438 (3) | C21C—H16C | 1.00 |
O02D—C02D | 1.436 (3) | C22C—H17C | 0.99 |
C01D—C02D | 1.524 (3) | C22C—H18C | 0.99 |
C01D—C11D | 1.536 (3) | C23C—H19C | 0.99 |
C02D—C21D | 1.531 (3) | C23C—H20C | 0.99 |
C11D—C12D | 1.532 (4) | C24C—H21C | 0.99 |
C11D—C16D | 1.521 (4) | C24C—H22C | 0.99 |
C12D—C13D | 1.538 (4) | C25C—H23C | 0.99 |
C13D—C14D | 1.517 (5) | C25C—H24C | 0.99 |
C14D—C15D | 1.520 (4) | C26C—H25C | 0.99 |
C15D—C16D | 1.532 (4) | C26C—H26C | 0.99 |
C21D—C22D | 1.526 (4) | C01D—H03D | 1.00 |
C21D—C26D | 1.537 (4) | C02D—H15D | 1.00 |
C22D—C23D | 1.529 (4) | C11D—H04D | 1.00 |
C23D—C24D | 1.526 (4) | C12D—H05D | 0.99 |
C24D—C25D | 1.513 (4) | C12D—H06D | 0.99 |
C25D—C26D | 1.518 (4) | C13D—H07D | 0.99 |
O01A—H01A | 0.90 (4) | C13D—H08D | 0.99 |
O02A—H02A | 1.05 (5) | C14D—H09D | 0.99 |
O01B—H01B | 0.95 (3) | C14D—H10D | 0.99 |
O02B—H02B | 0.95 (4) | C15D—H11D | 0.99 |
O01C—H01C | 0.93 (4) | C15D—H12D | 0.99 |
O02C—H02C | 0.97 (4) | C16D—H13D | 0.99 |
O01D—H01D | 0.85 (3) | C16D—H14D | 0.99 |
O02D—H02D | 0.91 (5) | C21D—H16D | 1.00 |
C01A—H03A | 1.00 | C22D—H17D | 0.99 |
C02A—H15A | 1.00 | C22D—H18D | 0.99 |
C11A—H04A | 1.00 | C23D—H19D | 0.99 |
C12A—H05A | 0.99 | C23D—H20D | 0.99 |
C12A—H06A | 0.99 | C24D—H21D | 0.99 |
C13A—H07A | 0.99 | C24D—H22D | 0.99 |
C13A—H08A | 0.99 | C25D—H23D | 0.99 |
C14A—H09A | 0.99 | C25D—H24D | 0.99 |
C14A—H10A | 0.99 | C26D—H25D | 0.99 |
C15A—H11A | 0.99 | C26D—H26D | 0.99 |
| | | |
O01A—C01A—C02A | 106.0 (2) | C16B—C15B—H12B | 109.3 |
O01A—C01A—C11A | 111.6 (2) | C11B—C16B—H13B | 109.1 |
C02A—C01A—C11A | 113.6 (2) | C11B—C16B—H14B | 109.1 |
O02A—C02A—C01A | 108.2 (2) | C15B—C16B—H13B | 109.1 |
O02A—C02A—C21A | 112.7 (2) | C15B—C16B—H14B | 109.1 |
C01A—C02A—C21A | 113.6 (2) | C02B—C21B—H16B | 107.4 |
C01A—C11A—C12A | 113.1 (2) | C22B—C21B—H16B | 107.4 |
C01A—C11A—C16A | 111.4 (2) | C26B—C21B—H16B | 107.4 |
C12A—C11A—C16A | 109.3 (2) | C21B—C22B—H17B | 109.1 |
C11A—C12A—C13A | 112.4 (2) | C21B—C22B—H18B | 109.1 |
C12A—C13A—C14A | 111.9 (3) | C23B—C22B—H17B | 109.1 |
C13A—C14A—C15A | 110.9 (3) | C23B—C22B—H18B | 109.1 |
C14A—C15A—C16A | 111.3 (3) | C22B—C23B—H19B | 109.3 |
C11A—C16A—C15A | 112.5 (3) | C22B—C23B—H20B | 109.3 |
C02A—C21A—C22A | 111.9 (2) | C24B—C23B—H19B | 109.3 |
C02A—C21A—C26A | 110.5 (2) | C24B—C23B—H20B | 109.3 |
C22A—C21A—C26A | 109.8 (2) | C23B—C24B—H21B | 109.5 |
C21A—C22A—C23A | 111.8 (2) | C23B—C24B—H22B | 109.5 |
C22A—C23A—C24A | 110.8 (2) | C25B—C24B—H21B | 109.5 |
C23A—C24A—C25A | 110.8 (3) | C25B—C24B—H22B | 109.5 |
C24A—C25A—C26A | 111.2 (2) | C24B—C25B—H23B | 109.4 |
C21A—C26A—C25A | 112.6 (2) | C24B—C25B—H24B | 109.4 |
O01B—C01B—C02B | 107.3 (2) | C26B—C25B—H23B | 109.4 |
O01B—C01B—C11B | 110.5 (2) | C26B—C25B—H24B | 109.4 |
C02B—C01B—C11B | 114.0 (2) | C21B—C26B—H25B | 109.0 |
O02B—C02B—C01B | 110.3 (2) | C21B—C26B—H26B | 109.0 |
O02B—C02B—C21B | 110.7 (2) | C25B—C26B—H25B | 109.0 |
C01B—C02B—C21B | 116.0 (2) | C25B—C26B—H26B | 109.0 |
C01B—C11B—C12B | 112.2 (2) | O01C—C01C—H03C | 108.7 |
C01B—C11B—C16B | 112.1 (2) | C02C—C01C—H03C | 108.7 |
C12B—C11B—C16B | 109.5 (2) | C11C—C01C—H03C | 108.7 |
C11B—C12B—C13B | 111.8 (2) | O02C—C02C—H15C | 107.4 |
C12B—C13B—C14B | 111.4 (3) | C01C—C02C—H15C | 107.4 |
C13B—C14B—C15B | 110.9 (3) | C21C—C02C—H15C | 107.4 |
C14B—C15B—C16B | 111.8 (2) | C01C—C11C—H04C | 107.7 |
C11B—C16B—C15B | 112.4 (2) | C12C—C11C—H04C | 107.7 |
C02B—C21B—C22B | 115.0 (2) | C16C—C11C—H04C | 107.7 |
C02B—C21B—C26B | 110.0 (2) | C11C—C12C—H05C | 109.2 |
C22B—C21B—C26B | 109.4 (2) | C11C—C12C—H06C | 109.2 |
C21B—C22B—C23B | 112.4 (3) | C13C—C12C—H05C | 109.2 |
C22B—C23B—C24B | 111.6 (3) | C13C—C12C—H06C | 109.2 |
C23B—C24B—C25B | 110.7 (3) | C12C—C13C—H07C | 109.2 |
C24B—C25B—C26B | 111.2 (3) | C12C—C13C—H08C | 109.2 |
C21B—C26B—C25B | 113.1 (2) | C14C—C13C—H07C | 109.2 |
O01C—C01C—C02C | 106.0 (2) | C14C—C13C—H08C | 109.2 |
O01C—C01C—C11C | 111.4 (2) | C13C—C14C—H09C | 109.5 |
C02C—C01C—C11C | 113.3 (2) | C13C—C14C—H10C | 109.5 |
O02C—C02C—C01C | 108.3 (2) | C15C—C14C—H09C | 109.5 |
O02C—C02C—C21C | 112.3 (2) | C15C—C14C—H10C | 109.5 |
C01C—C02C—C21C | 113.8 (2) | C14C—C15C—H11C | 109.4 |
C01C—C11C—C12C | 112.8 (2) | C14C—C15C—H12C | 109.4 |
C01C—C11C—C16C | 111.3 (2) | C16C—C15C—H11C | 109.4 |
C12C—C11C—C16C | 109.3 (2) | C16C—C15C—H12C | 109.4 |
C11C—C12C—C13C | 111.9 (2) | C11C—C16C—H13C | 109.2 |
C12C—C13C—C14C | 112.3 (3) | C11C—C16C—H14C | 109.2 |
C13C—C14C—C15C | 110.9 (3) | C15C—C16C—H13C | 109.2 |
C14C—C15C—C16C | 111.2 (3) | C15C—C16C—H14C | 109.2 |
C11C—C16C—C15C | 112.2 (3) | C02C—C21C—H16C | 107.9 |
C02C—C21C—C22C | 112.5 (2) | C22C—C21C—H16C | 107.9 |
C02C—C21C—C26C | 110.5 (2) | C26C—C21C—H16C | 107.9 |
C22C—C21C—C26C | 109.8 (2) | C21C—C22C—H17C | 109.2 |
C21C—C22C—C23C | 111.9 (2) | C21C—C22C—H18C | 109.2 |
C22C—C23C—C24C | 111.8 (3) | C23C—C22C—H17C | 109.2 |
C23C—C24C—C25C | 110.5 (3) | C23C—C22C—H18C | 109.2 |
C24C—C25C—C26C | 111.8 (2) | C22C—C23C—H19C | 109.2 |
C21C—C26C—C25C | 112.4 (2) | C22C—C23C—H20C | 109.2 |
O01D—C01D—C02D | 106.8 (2) | C24C—C23C—H19C | 109.2 |
O01D—C01D—C11D | 110.3 (2) | C24C—C23C—H20C | 109.2 |
C02D—C01D—C11D | 113.9 (2) | C23C—C24C—H21C | 109.5 |
O02D—C02D—C01D | 109.8 (2) | C23C—C24C—H22C | 109.5 |
O02D—C02D—C21D | 110.4 (2) | C25C—C24C—H21C | 109.5 |
C01D—C02D—C21D | 117.0 (2) | C25C—C24C—H22C | 109.5 |
C01D—C11D—C12D | 112.0 (2) | C24C—C25C—H23C | 109.3 |
C01D—C11D—C16D | 112.4 (2) | C24C—C25C—H24C | 109.3 |
C12D—C11D—C16D | 109.4 (2) | C26C—C25C—H23C | 109.3 |
C11D—C12D—C13D | 111.1 (2) | C26C—C25C—H24C | 109.3 |
C12D—C13D—C14D | 111.0 (2) | C21C—C26C—H25C | 109.1 |
C13D—C14D—C15D | 110.5 (2) | C21C—C26C—H26C | 109.1 |
C14D—C15D—C16D | 111.6 (2) | C25C—C26C—H25C | 109.1 |
C11D—C16D—C15D | 111.5 (2) | C25C—C26C—H26C | 109.1 |
C02D—C21D—C22D | 116.0 (2) | O01D—C01D—H03D | 108.6 |
C02D—C21D—C26D | 109.4 (2) | C02D—C01D—H03D | 108.6 |
C22D—C21D—C26D | 109.0 (2) | C11D—C01D—H03D | 108.6 |
C21D—C22D—C23D | 112.3 (2) | O02D—C02D—H15D | 106.4 |
C22D—C23D—C24D | 111.4 (2) | C01D—C02D—H15D | 106.4 |
C23D—C24D—C25D | 110.2 (3) | C21D—C02D—H15D | 106.4 |
C24D—C25D—C26D | 111.3 (2) | C01D—C11D—H04D | 107.6 |
C21D—C26D—C25D | 112.9 (2) | C12D—C11D—H04D | 107.6 |
C01A—O01A—H01A | 110 (3) | C16D—C11D—H04D | 107.6 |
C02A—O02A—H02A | 109 (3) | C11D—C12D—H05D | 109.4 |
C01B—O01B—H01B | 106 (2) | C11D—C12D—H06D | 109.4 |
C02B—O02B—H02B | 112 (2) | C13D—C12D—H05D | 109.4 |
C01C—O01C—H01C | 108 (2) | C13D—C12D—H06D | 109.4 |
C02C—O02C—H02C | 109 (2) | C12D—C13D—H07D | 109.4 |
C01D—O01D—H01D | 112 (2) | C12D—C13D—H08D | 109.4 |
C02D—O02D—H02D | 113 (3) | C14D—C13D—H07D | 109.4 |
O01A—C01A—H03A | 108.5 | C14D—C13D—H08D | 109.4 |
C02A—C01A—H03A | 108.5 | C13D—C14D—H09D | 109.6 |
C11A—C01A—H03A | 108.5 | C13D—C14D—H10D | 109.6 |
O02A—C02A—H15A | 107.3 | C15D—C14D—H09D | 109.6 |
C01A—C02A—H15A | 107.3 | C15D—C14D—H10D | 109.6 |
C21A—C02A—H15A | 107.3 | C14D—C15D—H11D | 109.3 |
C01A—C11A—H04A | 107.6 | C14D—C15D—H12D | 109.3 |
C12A—C11A—H04A | 107.6 | C16D—C15D—H11D | 109.3 |
C16A—C11A—H04A | 107.6 | C16D—C15D—H12D | 109.3 |
C11A—C12A—H05A | 109.1 | C11D—C16D—H13D | 109.3 |
C11A—C12A—H06A | 109.1 | C11D—C16D—H14D | 109.3 |
C13A—C12A—H05A | 109.1 | C15D—C16D—H13D | 109.3 |
C13A—C12A—H06A | 109.1 | C15D—C16D—H14D | 109.3 |
C12A—C13A—H07A | 109.2 | C02D—C21D—H16D | 107.4 |
C12A—C13A—H08A | 109.2 | C22D—C21D—H16D | 107.4 |
C14A—C13A—H07A | 109.2 | C26D—C21D—H16D | 107.4 |
C14A—C13A—H08A | 109.2 | C21D—C22D—H17D | 109.1 |
C13A—C14A—H09A | 109.5 | C21D—C22D—H18D | 109.1 |
C13A—C14A—H10A | 109.5 | C23D—C22D—H17D | 109.1 |
C15A—C14A—H09A | 109.5 | C23D—C22D—H18D | 109.1 |
C15A—C14A—H10A | 109.5 | C22D—C23D—H19D | 109.4 |
C14A—C15A—H11A | 109.4 | C22D—C23D—H20D | 109.4 |
C14A—C15A—H12A | 109.4 | C24D—C23D—H19D | 109.4 |
C16A—C15A—H11A | 109.4 | C24D—C23D—H20D | 109.4 |
C16A—C15A—H12A | 109.4 | C23D—C24D—H21D | 109.6 |
C11A—C16A—H13A | 109.1 | C23D—C24D—H22D | 109.6 |
C11A—C16A—H14A | 109.1 | C25D—C24D—H21D | 109.6 |
C15A—C16A—H13A | 109.1 | C25D—C24D—H22D | 109.6 |
C15A—C16A—H14A | 109.1 | C24D—C25D—H23D | 109.4 |
C02A—C21A—H16A | 108.2 | C24D—C25D—H24D | 109.4 |
C22A—C21A—H16A | 108.2 | C26D—C25D—H23D | 109.4 |
C26A—C21A—H16A | 108.2 | C26D—C25D—H24D | 109.4 |
C21A—C22A—H17A | 109.3 | C21D—C26D—H25D | 109.0 |
C21A—C22A—H18A | 109.3 | C21D—C26D—H26D | 109.0 |
C23A—C22A—H17A | 109.3 | C25D—C26D—H25D | 109.0 |
C23A—C22A—H18A | 109.3 | C25D—C26D—H26D | 109.0 |
C22A—C23A—H19A | 109.5 | H05A—C12A—H06A | 107.9 |
C22A—C23A—H20A | 109.5 | H07A—C13A—H08A | 107.9 |
C24A—C23A—H19A | 109.5 | H09A—C14A—H10A | 108.0 |
C24A—C23A—H20A | 109.5 | H11A—C15A—H12A | 108.0 |
C23A—C24A—H21A | 109.5 | H13A—C16A—H14A | 107.8 |
C23A—C24A—H22A | 109.5 | H17A—C22A—H18A | 107.9 |
C25A—C24A—H21A | 109.5 | H19A—C23A—H20A | 108.1 |
C25A—C24A—H22A | 109.5 | H21A—C24A—H22A | 108.1 |
C24A—C25A—H23A | 109.4 | H23A—C25A—H24A | 108.0 |
C24A—C25A—H24A | 109.4 | H25A—C26A—H26A | 107.8 |
C26A—C25A—H23A | 109.4 | H05B—C12B—H06B | 107.9 |
C26A—C25A—H24A | 109.4 | H07B—C13B—H08B | 108.0 |
C21A—C26A—H25A | 109.1 | H09B—C14B—H10B | 108.1 |
C21A—C26A—H26A | 109.1 | H11B—C15B—H12B | 107.9 |
C25A—C26A—H25A | 109.1 | H13B—C16B—H14B | 107.8 |
C25A—C26A—H26A | 109.1 | H17B—C22B—H18B | 107.8 |
O01B—C01B—H03B | 108.3 | H19B—C23B—H20B | 108.0 |
C02B—C01B—H03B | 108.3 | H21B—C24B—H22B | 108.1 |
C11B—C01B—H03B | 108.3 | H23B—C25B—H24B | 108.0 |
O02B—C02B—H15B | 106.4 | H25B—C26B—H26B | 107.8 |
C01B—C02B—H15B | 106.4 | H05C—C12C—H06C | 107.9 |
C21B—C02B—H15B | 106.4 | H07C—C13C—H08C | 107.9 |
C01B—C11B—H04B | 107.6 | H09C—C14C—H10C | 108.1 |
C12B—C11B—H04B | 107.6 | H11C—C15C—H12C | 108.0 |
C16B—C11B—H04B | 107.6 | H13C—C16C—H14C | 107.9 |
C11B—C12B—H05B | 109.3 | H17C—C22C—H18C | 107.9 |
C11B—C12B—H06B | 109.3 | H19C—C23C—H20C | 107.9 |
C13B—C12B—H05B | 109.3 | H21C—C24C—H22C | 108.1 |
C13B—C12B—H06B | 109.3 | H23C—C25C—H24C | 107.9 |
C12B—C13B—H07B | 109.3 | H25C—C26C—H26C | 107.9 |
C12B—C13B—H08B | 109.3 | H05D—C12D—H06D | 108.0 |
C14B—C13B—H07B | 109.3 | H07D—C13D—H08D | 108.0 |
C14B—C13B—H08B | 109.3 | H09D—C14D—H10D | 108.1 |
C13B—C14B—H09B | 109.5 | H11D—C15D—H12D | 108.0 |
C13B—C14B—H10B | 109.5 | H13D—C16D—H14D | 108.0 |
C15B—C14B—H09B | 109.5 | H17D—C22D—H18D | 107.9 |
C15B—C14B—H10B | 109.5 | H19D—C23D—H20D | 108.0 |
C14B—C15B—H11B | 109.3 | H21D—C24D—H22D | 108.1 |
C14B—C15B—H12B | 109.3 | H23D—C25D—H24D | 108.0 |
C16B—C15B—H11B | 109.3 | H25D—C26D—H26D | 107.8 |
| | | |
O01A—C01A—C11A—C16A | −166.8 (2) | O01C—C01C—C11C—C16C | −167.4 (2) |
C02A—C01A—C11A—C16A | 73.5 (3) | C02C—C01C—C11C—C16C | 73.2 (3) |
O01A—C01A—C11A—C12A | −43.2 (3) | O01C—C01C—C11C—C12C | −44.1 (3) |
C02A—C01A—C11A—C12A | −162.9 (3) | C02C—C01C—C11C—C12C | −163.5 (3) |
C16A—C11A—C12A—C13A | −54.8 (3) | C16C—C11C—C12C—C13C | −55.2 (3) |
C01A—C11A—C12A—C13A | −179.6 (3) | C01C—C11C—C12C—C13C | −179.6 (3) |
C11A—C12A—C13A—C14A | 55.8 (4) | C11C—C12C—C13C—C14C | 55.9 (4) |
C12A—C13A—C14A—C15A | −54.6 (4) | C12C—C13C—C14C—C15C | −54.8 (4) |
C13A—C14A—C15A—C16A | 54.2 (4) | C13C—C14C—C15C—C16C | 54.3 (4) |
C12A—C11A—C16A—C15A | 54.9 (3) | C12C—C11C—C16C—C15C | 55.4 (3) |
C01A—C11A—C16A—C15A | −179.4 (2) | C01C—C11C—C16C—C15C | −179.3 (2) |
C14A—C15A—C16A—C11A | −55.6 (4) | C14C—C15C—C16C—C11C | −55.9 (4) |
O01A—C01A—C02A—O02A | −63.0 (2) | O01C—C01C—C02C—O02C | −62.3 (2) |
C11A—C01A—C02A—O02A | 59.8 (3) | C11C—C01C—C02C—O02C | 60.1 (3) |
O01A—C01A—C02A—C21A | 62.9 (3) | O01C—C01C—C02C—C21C | 63.4 (3) |
C11A—C01A—C02A—C21A | −174.2 (2) | C11C—C01C—C02C—C21C | −174.2 (2) |
O02A—C02A—C21A—C26A | −162.0 (2) | O02C—C02C—C21C—C26C | −163.0 (2) |
C01A—C02A—C21A—C26A | 74.4 (3) | C01C—C02C—C21C—C26C | 73.4 (3) |
O02A—C02A—C21A—C22A | −39.3 (3) | O02C—C02C—C21C—C22C | −39.9 (3) |
C01A—C02A—C21A—C22A | −162.8 (3) | C01C—C02C—C21C—C22C | −163.4 (2) |
C26A—C21A—C22A—C23A | −55.1 (3) | C26C—C21C—C22C—C23C | −54.1 (3) |
C02A—C21A—C22A—C23A | −178.2 (2) | C02C—C21C—C22C—C23C | −177.7 (2) |
C21A—C22A—C23A—C24A | 57.2 (3) | C21C—C22C—C23C—C24C | 56.6 (3) |
C22A—C23A—C24A—C25A | −56.6 (3) | C22C—C23C—C24C—C25C | −56.0 (3) |
C23A—C24A—C25A—C26A | 55.3 (4) | C23C—C24C—C25C—C26C | 55.0 (3) |
C22A—C21A—C26A—C25A | 54.0 (3) | C24C—C25C—C26C—C21C | −54.8 (3) |
C02A—C21A—C26A—C25A | 177.9 (2) | C22C—C21C—C26C—C25C | 53.5 (3) |
C24A—C25A—C26A—C21A | −54.7 (4) | C02C—C21C—C26C—C25C | 178.2 (2) |
O01B—C01B—C11B—C16B | −171.6 (2) | O01D—C01D—C11D—C16D | −172.1 (2) |
C02B—C01B—C11B—C16B | 67.5 (3) | C02D—C01D—C11D—C16D | 67.9 (3) |
O01B—C01B—C11B—C12B | −47.9 (3) | O01D—C01D—C11D—C12D | −48.5 (3) |
C02B—C01B—C11B—C12B | −168.8 (3) | C02D—C01D—C11D—C12D | −168.5 (3) |
C16B—C11B—C12B—C13B | −56.0 (3) | C16D—C11D—C12D—C13D | −57.1 (3) |
C01B—C11B—C12B—C13B | 178.9 (2) | C01D—C11D—C12D—C13D | 177.6 (2) |
C11B—C12B—C13B—C14B | 57.5 (3) | C11D—C12D—C13D—C14D | 57.6 (3) |
C12B—C13B—C14B—C15B | −55.6 (3) | C12D—C13D—C14D—C15D | −56.0 (3) |
C13B—C14B—C15B—C16B | 53.7 (4) | C13D—C14D—C15D—C16D | 55.4 (4) |
C12B—C11B—C16B—C15B | 54.2 (3) | C12D—C11D—C16D—C15D | 56.4 (3) |
C01B—C11B—C16B—C15B | 179.5 (2) | C01D—C11D—C16D—C15D | −178.5 (2) |
C14B—C15B—C16B—C11B | −54.2 (3) | C14D—C15D—C16D—C11D | −56.4 (3) |
O01B—C01B—C02B—O02B | −65.2 (2) | O01D—C01D—C02D—O02D | −65.5 (3) |
C11B—C01B—C02B—O02B | 57.5 (3) | C11D—C01D—C02D—O02D | 56.5 (3) |
O01B—C01B—C02B—C21B | 61.7 (3) | O01D—C01D—C02D—C21D | 61.2 (3) |
C11B—C01B—C02B—C21B | −175.7 (2) | C11D—C01D—C02D—C21D | −176.8 (2) |
O02B—C02B—C21B—C22B | 49.2 (3) | O02D—C02D—C21D—C22D | 51.6 (3) |
C01B—C02B—C21B—C22B | −77.4 (3) | C01D—C02D—C21D—C22D | −74.8 (3) |
O02B—C02B—C21B—C26B | −74.8 (3) | O02D—C02D—C21D—C26D | −72.1 (3) |
C01B—C02B—C21B—C26B | 158.6 (3) | C01D—C02D—C21D—C26D | 161.5 (3) |
C26B—C21B—C22B—C23B | −53.9 (3) | C02D—C21D—C22D—C23D | −178.1 (2) |
C02B—C21B—C22B—C23B | −178.2 (2) | C26D—C21D—C22D—C23D | −54.2 (3) |
C21B—C22B—C23B—C24B | 56.5 (4) | C21D—C22D—C23D—C24D | 56.4 (3) |
C22B—C23B—C24B—C25B | −56.1 (4) | C22D—C23D—C24D—C25D | −56.0 (4) |
C23B—C24B—C25B—C26B | 54.9 (4) | C23D—C24D—C25D—C26D | 55.9 (3) |
C24B—C25B—C26B—C21B | −54.9 (3) | C24D—C25D—C26D—C21D | −56.4 (3) |
C22B—C21B—C26B—C25B | 53.3 (3) | C22D—C21D—C26D—C25D | 54.4 (3) |
C02B—C21B—C26B—C25B | −179.5 (2) | C02D—C21D—C26D—C25D | −177.8 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O01A—H01A···O02Ai | 0.90 (4) | 1.83 (4) | 2.724 (2) | 170 (4) |
O01B—H01B···O02Bii | 0.95 (3) | 1.72 (3) | 2.656 (3) | 169 (3) |
O01C—H01C···O02Ci | 0.93 (4) | 1.80 (4) | 2.730 (2) | 172 (3) |
O01D—H01D···O02Dii | 0.85 (3) | 1.81 (3) | 2.658 (3) | 174 (3) |
O02A—H02A···O01B | 1.05 (5) | 1.66 (5) | 2.682 (3) | 161 (4) |
O02B—H02B···O01A | 0.95 (4) | 1.87 (4) | 2.727 (3) | 149 (3) |
O02C—H02C···O01D | 0.97 (4) | 1.78 (4) | 2.698 (3) | 157 (3) |
O02D—H02D···O01C | 0.91 (5) | 1.88 (5) | 2.717 (3) | 152 (4) |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
(k98064) rac-1,2-dicyclohexylethane-1,2-diol
top
Crystal data top
C14H26O2 | Dx = 1.037 Mg m−3 |
Mr = 226.35 | Melting point: 147 C K |
Monoclinic, C12/c1 | Mo Kα radiation, λ = 0.71073 Å |
a = 23.153 (5) Å | Cell parameters from 13065 reflections |
b = 11.852 (3) Å | θ = 1.7–25.0° |
c = 10.926 (2) Å | µ = 0.07 mm−1 |
β = 104.64 (2)° | T = 295 K |
V = 2900.9 (11) Å3 | Laths. Largest faces are {100}; long direction is c., colourless |
Z = 8 | 0.31 × 0.22 × 0.13 mm |
F(000) = 1008 | |
Data collection top
Nonius Kappa-CCD diffractometer | 1942 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 25.0°, θmin = 2.6° |
Detector resolution: 18 pixels mm-1 | h = −26→27 |
ϕ and ω scans with 1.0° steps | k = −14→14 |
4869 measured reflections | l = −12→0 |
2529 independent reflections | |
Refinement top
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)] = 0.068 | Hydrogen site location: mixed |
wR(F2) = 0.208 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | w = 1/[σ2(Fo2) + (0.11P)2 + 0.59P] where P = (Fo2 + 2Fc2)/3 |
2529 reflections | (Δ/σ)max < 0.001 |
211 parameters | Δρmax = 0.14 e Å−3 |
64 restraints | Δρmin = −0.12 e Å−3 |
Crystal data top
C14H26O2 | V = 2900.9 (11) Å3 |
Mr = 226.35 | Z = 8 |
Monoclinic, C12/c1 | Mo Kα radiation |
a = 23.153 (5) Å | µ = 0.07 mm−1 |
b = 11.852 (3) Å | T = 295 K |
c = 10.926 (2) Å | 0.31 × 0.22 × 0.13 mm |
β = 104.64 (2)° | |
Data collection top
Nonius Kappa-CCD diffractometer | 1942 reflections with I > 2σ(I) |
4869 measured reflections | Rint = 0.023 |
2529 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.068 | 64 restraints |
wR(F2) = 0.208 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | Δρmax = 0.14 e Å−3 |
2529 reflections | Δρmin = −0.12 e Å−3 |
211 parameters | |
Special details top
Experimental. The crystal-to-detector distance was 25 mm. Each frame was measured for 240 s. The number of scan sets measured was 2; the total number of frames measured was 222. |
Refinement. The hydroxyl H atoms were located in difference maps. U values were 1.2 times the equivalent U values of the attached O atoms. The O—H distances were restrained (DFIX 0.84 (1)). All other H atoms were placed in calculated positions. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O01 | 0.00320 (8) | 0.86884 (15) | 0.13101 (14) | 0.0858 (6) | |
H91A | −0.009 (2) | 0.855 (4) | 0.196 (3) | 0.103* | 0.50 |
H91B | −0.002 (2) | 0.935 (2) | 0.104 (5) | 0.103* | 0.50 |
O02 | 0.00741 (7) | 0.90575 (16) | −0.12551 (14) | 0.0815 (6) | |
H92A | 0.012 (2) | 0.903 (4) | −0.199 (2) | 0.098* | 0.50 |
H92B | 0.023 (2) | 0.969 (2) | −0.121 (5) | 0.098* | 0.50 |
C01 | 0.00935 (8) | 0.78050 (16) | 0.04696 (15) | 0.0576 (5) | |
H01 | 0.0330 | 0.7203 | 0.0973 | 0.069* | |
C02 | 0.04468 (8) | 0.82661 (17) | −0.04236 (15) | 0.0580 (5) | |
H02 | 0.0528 | 0.7637 | −0.0938 | 0.070* | |
C11 | −0.05141 (8) | 0.73155 (17) | −0.01917 (16) | 0.0610 (5) | |
H11 | −0.0749 | 0.7922 | −0.0690 | 0.073* | |
C12 | −0.08477 (12) | 0.6922 (3) | 0.0772 (2) | 0.0940 (8) | |
H12A | −0.0608 | 0.6365 | 0.1325 | 0.113* | |
H12B | −0.0903 | 0.7559 | 0.1288 | 0.113* | |
C13 | −0.14533 (13) | 0.6413 (3) | 0.0146 (3) | 0.1127 (10) | |
H13A | −0.1639 | 0.6142 | 0.0794 | 0.135* | |
H13B | −0.1709 | 0.6990 | −0.0338 | 0.135* | |
C14 | −0.13966 (14) | 0.5461 (3) | −0.0707 (3) | 0.1199 (11) | |
H14A | −0.1790 | 0.5178 | −0.1123 | 0.144* | |
H14B | −0.1173 | 0.4851 | −0.0212 | 0.144* | |
C15 | −0.10837 (14) | 0.5841 (3) | −0.1686 (3) | 0.1252 (12) | |
H15A | −0.1332 | 0.6388 | −0.2241 | 0.150* | |
H15B | −0.1029 | 0.5199 | −0.2196 | 0.150* | |
C16 | −0.04750 (11) | 0.6372 (2) | −0.1086 (3) | 0.0918 (8) | |
H16A | −0.0209 | 0.5795 | −0.0631 | 0.110* | |
H16B | −0.0305 | 0.6660 | −0.1750 | 0.110* | |
C21A | 0.1061 (6) | 0.8740 (19) | 0.032 (2) | 0.067 (4) | 0.50 |
H21A | 0.0982 | 0.9249 | 0.0962 | 0.081* | 0.50 |
C22A | 0.1356 (6) | 0.9452 (12) | −0.0521 (12) | 0.097 (4) | 0.50 |
H22A | 0.1091 | 1.0065 | −0.0889 | 0.116* | 0.50 |
H22B | 0.1421 | 0.8989 | −0.1206 | 0.116* | 0.50 |
C23A | 0.1951 (7) | 0.9936 (13) | 0.0229 (16) | 0.120 (4) | 0.50 |
H23A | 0.2144 | 1.0328 | −0.0340 | 0.144* | 0.50 |
H23B | 0.1882 | 1.0476 | 0.0843 | 0.144* | 0.50 |
C24A | 0.2353 (6) | 0.9011 (18) | 0.0900 (19) | 0.124 (5) | 0.50 |
H24A | 0.2721 | 0.9341 | 0.1402 | 0.148* | 0.50 |
H24B | 0.2454 | 0.8517 | 0.0278 | 0.148* | 0.50 |
C25A | 0.2067 (9) | 0.8326 (18) | 0.175 (2) | 0.133 (5) | 0.50 |
H25A | 0.2003 | 0.8801 | 0.2428 | 0.160* | 0.50 |
H25B | 0.2334 | 0.7719 | 0.2131 | 0.160* | 0.50 |
C26A | 0.1468 (7) | 0.7828 (14) | 0.1012 (17) | 0.089 (3) | 0.50 |
H26A | 0.1538 | 0.7275 | 0.0411 | 0.107* | 0.50 |
H26B | 0.1278 | 0.7448 | 0.1593 | 0.107* | 0.50 |
C21B | 0.1027 (7) | 0.886 (2) | 0.017 (2) | 0.065 (3) | 0.50 |
H21B | 0.0934 | 0.9525 | 0.0608 | 0.078* | 0.50 |
C22B | 0.1337 (6) | 0.9262 (15) | −0.0836 (14) | 0.114 (5) | 0.50 |
H22C | 0.1070 | 0.9753 | −0.1432 | 0.137* | 0.50 |
H22D | 0.1431 | 0.8618 | −0.1299 | 0.137* | 0.50 |
C23B | 0.1913 (8) | 0.9902 (18) | −0.0215 (16) | 0.142 (7) | 0.50 |
H23C | 0.2103 | 1.0149 | −0.0866 | 0.171* | 0.50 |
H23D | 0.1814 | 1.0569 | 0.0205 | 0.171* | 0.50 |
C24B | 0.2340 (7) | 0.920 (2) | 0.072 (2) | 0.141 (7) | 0.50 |
H24C | 0.2686 | 0.9647 | 0.1125 | 0.169* | 0.50 |
H24D | 0.2475 | 0.8573 | 0.0290 | 0.169* | 0.50 |
C25B | 0.2046 (9) | 0.8745 (18) | 0.1719 (17) | 0.135 (7) | 0.50 |
H25C | 0.1970 | 0.9365 | 0.2236 | 0.162* | 0.50 |
H25D | 0.2316 | 0.8223 | 0.2264 | 0.162* | 0.50 |
C26B | 0.1460 (8) | 0.8143 (13) | 0.1121 (15) | 0.100 (5) | 0.50 |
H26C | 0.1545 | 0.7461 | 0.0709 | 0.120* | 0.50 |
H26D | 0.1272 | 0.7923 | 0.1784 | 0.120* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O01 | 0.1187 (13) | 0.0891 (12) | 0.0598 (9) | −0.0275 (10) | 0.0414 (9) | −0.0249 (8) |
O02 | 0.0808 (10) | 0.0954 (12) | 0.0679 (9) | −0.0045 (8) | 0.0178 (8) | 0.0356 (9) |
C01 | 0.0734 (12) | 0.0591 (11) | 0.0403 (8) | −0.0075 (9) | 0.0145 (8) | −0.0007 (7) |
C02 | 0.0689 (12) | 0.0632 (11) | 0.0423 (8) | −0.0045 (9) | 0.0147 (8) | 0.0011 (8) |
C11 | 0.0674 (12) | 0.0631 (12) | 0.0518 (9) | −0.0065 (9) | 0.0136 (8) | 0.0046 (8) |
C12 | 0.0974 (17) | 0.110 (2) | 0.0837 (15) | −0.0367 (15) | 0.0390 (13) | −0.0038 (14) |
C13 | 0.0945 (19) | 0.118 (2) | 0.134 (2) | −0.0335 (18) | 0.0450 (18) | 0.002 (2) |
C14 | 0.097 (2) | 0.110 (2) | 0.146 (3) | −0.0494 (18) | 0.0180 (18) | −0.005 (2) |
C15 | 0.112 (2) | 0.140 (3) | 0.116 (2) | −0.052 (2) | 0.0151 (18) | −0.053 (2) |
C16 | 0.0883 (16) | 0.0982 (18) | 0.0899 (15) | −0.0265 (14) | 0.0242 (13) | −0.0314 (14) |
C21A | 0.063 (5) | 0.080 (9) | 0.059 (6) | −0.016 (4) | 0.015 (4) | −0.004 (5) |
C22A | 0.078 (5) | 0.106 (5) | 0.097 (8) | −0.004 (4) | 0.005 (4) | 0.033 (5) |
C23A | 0.078 (5) | 0.127 (7) | 0.145 (12) | −0.036 (5) | 0.007 (6) | 0.038 (6) |
C24A | 0.067 (6) | 0.154 (10) | 0.133 (9) | −0.024 (6) | −0.006 (6) | 0.014 (8) |
C25A | 0.079 (6) | 0.150 (12) | 0.146 (9) | −0.022 (6) | −0.015 (5) | 0.045 (7) |
C26A | 0.062 (4) | 0.087 (7) | 0.108 (6) | −0.001 (4) | −0.001 (4) | 0.014 (4) |
C21B | 0.076 (6) | 0.065 (5) | 0.055 (5) | −0.004 (4) | 0.018 (4) | 0.012 (4) |
C22B | 0.087 (5) | 0.183 (10) | 0.081 (5) | −0.055 (5) | 0.036 (4) | 0.022 (5) |
C23B | 0.089 (7) | 0.205 (12) | 0.125 (10) | −0.051 (6) | 0.011 (6) | 0.069 (8) |
C24B | 0.076 (7) | 0.171 (13) | 0.178 (12) | −0.026 (8) | 0.035 (6) | 0.062 (10) |
C25B | 0.089 (7) | 0.184 (17) | 0.109 (7) | −0.049 (9) | −0.020 (5) | 0.067 (9) |
C26B | 0.088 (7) | 0.109 (10) | 0.096 (6) | −0.026 (6) | 0.010 (5) | 0.038 (7) |
Geometric parameters (Å, º) top
O01—C01 | 1.423 (2) | C12—H12B | 0.97 |
O02—C02 | 1.433 (2) | C13—H13A | 0.97 |
C01—C02 | 1.524 (2) | C13—H13B | 0.97 |
C01—C11 | 1.525 (3) | C14—H14A | 0.97 |
C11—C12 | 1.527 (3) | C14—H14B | 0.97 |
C11—C16 | 1.503 (3) | C15—H15A | 0.97 |
C12—C13 | 1.521 (3) | C15—H15B | 0.97 |
C13—C14 | 1.490 (4) | C16—H16A | 0.97 |
C14—C15 | 1.505 (4) | C16—H16B | 0.97 |
C15—C16 | 1.531 (3) | C21A—H21A | 0.98 |
C02—C21A | 1.553 (18) | C21B—H21B | 0.98 |
C21A—C22A | 1.526 (10) | C22A—H22A | 0.97 |
C21A—C26A | 1.507 (12) | C22A—H22B | 0.97 |
C22A—C23A | 1.526 (10) | C22B—H22C | 0.97 |
C23A—C24A | 1.503 (12) | C22B—H22D | 0.97 |
C24A—C25A | 1.509 (11) | C23A—H23A | 0.97 |
C25A—C26A | 1.535 (11) | C23A—H23B | 0.97 |
C02—C21B | 1.51 (2) | C23B—H23C | 0.97 |
C21B—C22B | 1.530 (12) | C23B—H23D | 0.97 |
C21B—C26B | 1.510 (10) | C24A—H24A | 0.97 |
C22B—C23B | 1.536 (11) | C24A—H24B | 0.97 |
C23B—C24B | 1.486 (11) | C24B—H24C | 0.97 |
C24B—C25B | 1.522 (12) | C24B—H24D | 0.97 |
C25B—C26B | 1.527 (10) | C25A—H25A | 0.97 |
O01—H91A | 0.84 (2) | C25A—H25B | 0.97 |
O01—H91B | 0.84 (2) | C25B—H25C | 0.97 |
O02—H92A | 0.83 (2) | C25B—H25D | 0.97 |
O02—H92B | 0.84 (2) | C26A—H26A | 0.97 |
C01—H01 | 0.98 | C26A—H26B | 0.97 |
C02—H02 | 0.98 | C26B—H26C | 0.97 |
C11—H11 | 0.98 | C26B—H26D | 0.97 |
C12—H12A | 0.97 | | |
| | | |
O01—C01—C02 | 107.86 (15) | C11—C16—H16B | 109.1 |
O01—C01—C11 | 110.78 (16) | C15—C16—H16A | 109.1 |
C02—C01—C11 | 114.41 (13) | C15—C16—H16B | 109.1 |
O02—C02—C01 | 107.81 (15) | C02—C21A—H21A | 106.5 |
O02—C02—C21A | 114.8 (7) | C22A—C21A—H21A | 106.5 |
O02—C02—C21B | 107.2 (7) | C26A—C21A—H21A | 106.5 |
C01—C02—C21A | 111.4 (7) | C02—C21B—H21B | 107.6 |
C01—C02—C21B | 117.3 (7) | C22B—C21B—H21B | 107.6 |
C01—C11—C12 | 110.88 (15) | C26B—C21B—H21B | 107.6 |
C01—C11—C16 | 113.03 (17) | C21A—C22A—H22A | 109.3 |
C12—C11—C16 | 110.20 (19) | C21A—C22A—H22B | 109.3 |
C11—C12—C13 | 112.4 (2) | C23A—C22A—H22A | 109.3 |
C12—C13—C14 | 111.4 (2) | C23A—C22A—H22B | 109.3 |
C13—C14—C15 | 110.6 (3) | C21B—C22B—H22C | 109.5 |
C14—C15—C16 | 112.0 (2) | C21B—C22B—H22D | 109.5 |
C11—C16—C15 | 112.6 (2) | C23B—C22B—H22C | 109.5 |
C02—C21A—C22A | 112.2 (12) | C23B—C22B—H22D | 109.5 |
C02—C21A—C26A | 112.2 (14) | C22A—C23A—H23A | 109.5 |
C22A—C21A—C26A | 112.4 (11) | C22A—C23A—H23B | 109.5 |
C21A—C22A—C23A | 111.5 (10) | C24A—C23A—H23A | 109.5 |
C22A—C23A—C24A | 110.6 (9) | C24A—C23A—H23B | 109.5 |
C23A—C24A—C25A | 112.3 (11) | C22B—C23B—H23C | 109.1 |
C24A—C25A—C26A | 111.2 (11) | C22B—C23B—H23D | 109.1 |
C21A—C26A—C25A | 110.9 (12) | C24B—C23B—H23C | 109.1 |
C02—C21B—C22B | 111.6 (15) | C24B—C23B—H23D | 109.1 |
C02—C21B—C26B | 113.5 (14) | C23A—C24A—H24A | 109.1 |
C22B—C21B—C26B | 108.8 (11) | C23A—C24A—H24B | 109.1 |
C21B—C22B—C23B | 110.5 (12) | C25A—C24A—H24A | 109.1 |
C22B—C23B—C24B | 112.3 (12) | C25A—C24A—H24B | 109.1 |
C23B—C24B—C25B | 110.6 (10) | C23B—C24B—H24C | 109.5 |
C24B—C25B—C26B | 111.6 (12) | C23B—C24B—H24D | 109.5 |
C21B—C26B—C25B | 113.4 (11) | C25B—C24B—H24C | 109.5 |
C01—O01—H91A | 121 (3) | C25B—C24B—H24D | 109.5 |
C01—O01—H91B | 119 (4) | C24A—C25A—H25A | 109.4 |
H91A—O01—H91B | 115 (5) | C24A—C25A—H25B | 109.4 |
C02—O02—H92A | 113 (4) | C26A—C25A—H25A | 109.4 |
C02—O02—H92B | 112 (4) | C26A—C25A—H25B | 109.4 |
H92A—O02—H92B | 86 (5) | C24B—C25B—H25C | 109.3 |
O01—C01—H01 | 107.8 | C24B—C25B—H25D | 109.3 |
C02—C01—H01 | 107.8 | C26B—C25B—H25C | 109.3 |
C11—C01—H01 | 107.9 | C26B—C25B—H25D | 109.3 |
O02—C02—H02 | 107.8 | C21A—C26A—H26A | 109.5 |
C01—C02—H02 | 107.8 | C21A—C26A—H26B | 109.5 |
C21A—C02—H02 | 106.9 | C25A—C26A—H26A | 109.5 |
C21B—C02—H02 | 108.6 | C25A—C26A—H26B | 109.5 |
C01—C11—H11 | 107.5 | C21B—C26B—H26C | 108.9 |
C12—C11—H11 | 107.5 | C21B—C26B—H26D | 108.9 |
C16—C11—H11 | 107.5 | C25B—C26B—H26C | 108.9 |
C11—C12—H12A | 109.1 | C25B—C26B—H26D | 108.9 |
C11—C12—H12B | 109.1 | H12A—C12—H12B | 107.9 |
C13—C12—H12A | 109.1 | H13A—C13—H13B | 108.0 |
C13—C12—H12B | 109.1 | H14A—C14—H14B | 108.1 |
C12—C13—H13A | 109.4 | H15A—C15—H15B | 107.9 |
C12—C13—H13B | 109.4 | H16A—C16—H16B | 107.8 |
C14—C13—H13A | 109.4 | H22A—C22A—H22B | 108.0 |
C14—C13—H13B | 109.4 | H22C—C22B—H22D | 108.1 |
C13—C14—H14A | 109.5 | H23A—C23A—H23B | 108.1 |
C13—C14—H14B | 109.5 | H23C—C23B—H23D | 107.9 |
C15—C14—H14A | 109.5 | H24A—C24A—H24B | 107.9 |
C15—C14—H14B | 109.5 | H24C—C24B—H24D | 108.1 |
C14—C15—H15A | 109.2 | H25A—C25A—H25B | 108.0 |
C14—C15—H15B | 109.2 | H25C—C25B—H25D | 108.0 |
C16—C15—H15A | 109.2 | H26A—C26A—H26B | 108.0 |
C16—C15—H15B | 109.2 | H26C—C26B—H26D | 107.7 |
C11—C16—H16A | 109.1 | | |
| | | |
O01—C01—C02—O02 | −70.08 (18) | C01—C02—C21A—C22A | −166.3 (11) |
C11—C01—C02—O02 | 53.7 (2) | C26A—C21A—C22A—C23A | −54 (2) |
O01—C01—C02—C21B | 50.9 (10) | C02—C21A—C22A—C23A | 178.5 (14) |
C11—C01—C02—C21B | 174.7 (10) | C21A—C22A—C23A—C24A | 54.3 (18) |
O01—C01—C02—C21A | 56.7 (9) | C22A—C23A—C24A—C25A | −56.2 (19) |
C11—C01—C02—C21A | −179.5 (9) | C23A—C24A—C25A—C26A | 56 (2) |
O01—C01—C11—C16 | −179.62 (18) | C22A—C21A—C26A—C25A | 53 (2) |
C02—C01—C11—C16 | 58.2 (2) | C02—C21A—C26A—C25A | −179.0 (16) |
O01—C01—C11—C12 | −55.3 (2) | C24A—C25A—C26A—C21A | −54 (2) |
C02—C01—C11—C12 | −177.49 (19) | O02—C02—C21B—C26B | 177.2 (13) |
C16—C11—C12—C13 | −53.3 (3) | C01—C02—C21B—C26B | 55.9 (19) |
C01—C11—C12—C13 | −179.2 (2) | C21A—C02—C21B—C26B | 12 (12) |
C11—C12—C13—C14 | 56.2 (4) | O02—C02—C21B—C22B | −59.4 (17) |
C12—C13—C14—C15 | −56.4 (4) | C01—C02—C21B—C22B | 179.3 (10) |
C13—C14—C15—C16 | 55.3 (4) | C21A—C02—C21B—C22B | 136 (15) |
C01—C11—C16—C15 | 176.7 (2) | C26B—C21B—C22B—C23B | −56 (2) |
C12—C11—C16—C15 | 52.0 (3) | C02—C21B—C22B—C23B | 177.7 (16) |
C14—C15—C16—C11 | −54.1 (4) | C21B—C22B—C23B—C24B | 59 (2) |
O02—C02—C21A—C26A | −171.0 (11) | C22B—C23B—C24B—C25B | −56 (2) |
C21B—C02—C21A—C26A | −155 (15) | C23B—C24B—C25B—C26B | 53 (2) |
C01—C02—C21A—C26A | 66.1 (16) | C02—C21B—C26B—C25B | −179.8 (17) |
O02—C02—C21A—C22A | −43.4 (18) | C22B—C21B—C26B—C25B | 55 (2) |
C21B—C02—C21A—C22A | −28 (13) | C24B—C25B—C26B—C21B | −54 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O01—H91A···O01i | 0.84 (2) | 1.87 (2) | 2.641 (3) | 152 (5) |
O01—H91B···O02ii | 0.84 (2) | 1.91 (3) | 2.682 (3) | 153 (6) |
O02—H92A···O02iii | 0.83 (2) | 1.86 (2) | 2.654 (3) | 160 (5) |
O02—H92B···O01ii | 0.84 (2) | 2.01 (4) | 2.682 (3) | 138 (5) |
Symmetry codes: (i) −x, y, −z+1/2; (ii) −x, −y+2, −z; (iii) −x, y, −z−1/2. |
(k00013) rac-1,2-dicyclohexylethane-1,2-diol
top
Crystal data top
C14H26O2 | Dx = 1.063 Mg m−3 |
Mr = 226.35 | Melting point: 147 C K |
Monoclinic, C12/c1 | Mo Kα radiation, λ = 0.71073 Å |
a = 23.161 (5) Å | Cell parameters from 9027 reflections |
b = 11.584 (3) Å | θ = 1.0–25.0° |
c = 10.973 (2) Å | µ = 0.07 mm−1 |
β = 106.10 (2)° | T = 173 K |
V = 2828.6 (11) Å3 | Laths. Largest faces are {100}; long direction is c., colourless |
Z = 8 | 0.56 × 0.55 × 0.10 mm |
F(000) = 1008 | |
Data collection top
Nonius Kappa-CCD diffractometer | 1911 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.021 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
Detector resolution: 18 pixels mm-1 | h = −27→27 |
ϕ and ω scans with 2.0° steps | k = −13→13 |
4693 measured reflections | l = −13→13 |
2489 independent reflections | |
Refinement top
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)] = 0.047 | Hydrogen site location: mixed |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.048P)2 + 1.16P] where P = (Fo2 + 2Fc2)/3 |
2489 reflections | (Δ/σ)max < 0.001 |
211 parameters | Δρmax = 0.15 e Å−3 |
64 restraints | Δρmin = −0.19 e Å−3 |
Crystal data top
C14H26O2 | V = 2828.6 (11) Å3 |
Mr = 226.35 | Z = 8 |
Monoclinic, C12/c1 | Mo Kα radiation |
a = 23.161 (5) Å | µ = 0.07 mm−1 |
b = 11.584 (3) Å | T = 173 K |
c = 10.973 (2) Å | 0.56 × 0.55 × 0.10 mm |
β = 106.10 (2)° | |
Data collection top
Nonius Kappa-CCD diffractometer | 1911 reflections with I > 2σ(I) |
4693 measured reflections | Rint = 0.021 |
2489 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.047 | 64 restraints |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.15 e Å−3 |
2489 reflections | Δρmin = −0.19 e Å−3 |
211 parameters | |
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 5; the total number of frames measured was 226. |
Refinement. The hydroxyl H atoms were located in difference maps. U values were 1.2 times the equivalent U values of the attached O atoms. The O—H distances were restrained (DFIX 0.86 (1)). All other H atoms were placed in calculated positions. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O01 | 0.00852 (5) | 0.86681 (10) | 0.13541 (10) | 0.0490 (3) | |
H91A | −0.0037 (15) | 0.850 (3) | 0.200 (2) | 0.059* | 0.50 |
H91B | −0.0080 (15) | 0.9299 (18) | 0.106 (3) | 0.059* | 0.50 |
O02 | 0.00541 (5) | 0.90468 (11) | −0.12722 (11) | 0.0531 (4) | |
H92A | 0.0080 (17) | 0.902 (3) | −0.2021 (15) | 0.064* | 0.50 |
H92B | −0.0029 (16) | 0.9757 (11) | −0.128 (4) | 0.064* | 0.50 |
C01 | 0.01143 (6) | 0.77787 (12) | 0.04737 (11) | 0.0314 (3) | |
H01 | 0.0351 | 0.7176 | 0.0977 | 0.038* | |
C02 | 0.04474 (6) | 0.82578 (12) | −0.04343 (12) | 0.0319 (4) | |
H02 | 0.0528 | 0.7629 | −0.0949 | 0.038* | |
C11 | −0.05120 (6) | 0.73106 (12) | −0.01791 (12) | 0.0316 (4) | |
H11 | −0.0756 | 0.7964 | −0.0655 | 0.038* | |
C12 | −0.08270 (7) | 0.68793 (15) | 0.07867 (14) | 0.0465 (4) | |
H12A | −0.0578 | 0.6271 | 0.1316 | 0.056* | |
H12B | −0.0863 | 0.7525 | 0.1352 | 0.056* | |
C13 | −0.14482 (7) | 0.63967 (15) | 0.01596 (16) | 0.0533 (5) | |
H13A | −0.1626 | 0.6098 | 0.0819 | 0.064* | |
H13B | −0.1710 | 0.7022 | −0.0302 | 0.064* | |
C14 | −0.14204 (8) | 0.54396 (16) | −0.07531 (19) | 0.0616 (5) | |
H14A | −0.1832 | 0.5169 | −0.1181 | 0.074* | |
H14B | −0.1191 | 0.4781 | −0.0281 | 0.074* | |
C15 | −0.11206 (7) | 0.58586 (17) | −0.17386 (17) | 0.0620 (5) | |
H15A | −0.1377 | 0.6453 | −0.2276 | 0.074* | |
H15B | −0.1083 | 0.5205 | −0.2293 | 0.074* | |
C16 | −0.04989 (7) | 0.63666 (14) | −0.11326 (15) | 0.0458 (4) | |
H16A | −0.0226 | 0.5743 | −0.0701 | 0.055* | |
H16B | −0.0336 | 0.6688 | −0.1806 | 0.055* | |
C21A | 0.1078 (5) | 0.8816 (11) | 0.0323 (13) | 0.030 (2) | 0.50 |
H21A | 0.1018 | 0.9336 | 0.1005 | 0.036* | 0.50 |
C22A | 0.1338 (5) | 0.9510 (9) | −0.0592 (9) | 0.041 (2) | 0.50 |
H22A | 0.1395 | 0.8995 | −0.1270 | 0.049* | 0.50 |
H22B | 0.1053 | 1.0126 | −0.0994 | 0.049* | 0.50 |
C23A | 0.1937 (6) | 1.0044 (10) | 0.0109 (10) | 0.0510 (19) | 0.50 |
H23A | 0.2101 | 1.0467 | −0.0503 | 0.061* | 0.50 |
H23B | 0.1871 | 1.0608 | 0.0736 | 0.061* | 0.50 |
C24A | 0.2385 (6) | 0.9167 (15) | 0.0780 (14) | 0.069 (4) | 0.50 |
H24A | 0.2739 | 0.9571 | 0.1329 | 0.083* | 0.50 |
H24B | 0.2522 | 0.8720 | 0.0143 | 0.083* | 0.50 |
C25A | 0.2141 (4) | 0.8324 (6) | 0.1597 (9) | 0.060 (2) | 0.50 |
H25A | 0.2424 | 0.7670 | 0.1847 | 0.072* | 0.50 |
H25B | 0.2119 | 0.8724 | 0.2380 | 0.072* | 0.50 |
C26A | 0.1520 (5) | 0.7857 (9) | 0.0913 (10) | 0.0431 (19) | 0.50 |
H26A | 0.1361 | 0.7417 | 0.1523 | 0.052* | 0.50 |
H26B | 0.1557 | 0.7318 | 0.0238 | 0.052* | 0.50 |
C21B | 0.1022 (5) | 0.8842 (11) | 0.0105 (12) | 0.033 (2) | 0.50 |
H21B | 0.0927 | 0.9545 | 0.0543 | 0.040* | 0.50 |
C22B | 0.1328 (5) | 0.9275 (10) | −0.0865 (10) | 0.053 (2) | 0.50 |
H22C | 0.1055 | 0.9814 | −0.1454 | 0.063* | 0.50 |
H22D | 0.1407 | 0.8614 | −0.1367 | 0.063* | 0.50 |
C23B | 0.1919 (6) | 0.9890 (11) | −0.0247 (10) | 0.067 (3) | 0.50 |
H23C | 0.2107 | 1.0141 | −0.0910 | 0.080* | 0.50 |
H23D | 0.1839 | 1.0585 | 0.0206 | 0.080* | 0.50 |
C24B | 0.2341 (6) | 0.9105 (15) | 0.0671 (15) | 0.067 (3) | 0.50 |
H24C | 0.2728 | 0.9502 | 0.1044 | 0.080* | 0.50 |
H24D | 0.2420 | 0.8403 | 0.0228 | 0.080* | 0.50 |
C25B | 0.2044 (4) | 0.8768 (6) | 0.1738 (9) | 0.060 (2) | 0.50 |
H25C | 0.2319 | 0.8268 | 0.2373 | 0.073* | 0.50 |
H25D | 0.1960 | 0.9471 | 0.2174 | 0.073* | 0.50 |
C26B | 0.1456 (5) | 0.8122 (9) | 0.1134 (10) | 0.049 (2) | 0.50 |
H26C | 0.1260 | 0.7923 | 0.1801 | 0.058* | 0.50 |
H26D | 0.1548 | 0.7393 | 0.0756 | 0.058* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O01 | 0.0599 (8) | 0.0552 (8) | 0.0392 (6) | −0.0180 (6) | 0.0258 (6) | −0.0202 (6) |
O02 | 0.0430 (7) | 0.0629 (8) | 0.0558 (7) | 0.0093 (6) | 0.0175 (6) | 0.0346 (7) |
C01 | 0.0393 (8) | 0.0312 (8) | 0.0230 (7) | −0.0036 (6) | 0.0076 (6) | −0.0011 (6) |
C02 | 0.0374 (9) | 0.0326 (8) | 0.0264 (7) | 0.0013 (7) | 0.0100 (6) | 0.0016 (6) |
C11 | 0.0348 (8) | 0.0316 (8) | 0.0276 (7) | −0.0028 (6) | 0.0073 (6) | 0.0030 (6) |
C12 | 0.0469 (10) | 0.0515 (10) | 0.0428 (8) | −0.0146 (8) | 0.0153 (7) | 0.0026 (8) |
C13 | 0.0448 (10) | 0.0553 (11) | 0.0617 (10) | −0.0144 (8) | 0.0177 (8) | 0.0067 (9) |
C14 | 0.0435 (10) | 0.0491 (11) | 0.0845 (13) | −0.0169 (9) | 0.0049 (9) | −0.0006 (10) |
C15 | 0.0492 (11) | 0.0657 (12) | 0.0648 (11) | −0.0138 (9) | 0.0053 (9) | −0.0281 (10) |
C16 | 0.0417 (9) | 0.0476 (10) | 0.0461 (9) | −0.0058 (7) | 0.0091 (7) | −0.0126 (7) |
C21A | 0.031 (3) | 0.038 (4) | 0.022 (3) | −0.017 (3) | 0.007 (3) | 0.000 (2) |
C22A | 0.041 (3) | 0.042 (3) | 0.040 (4) | 0.000 (2) | 0.012 (3) | 0.013 (3) |
C23A | 0.042 (3) | 0.051 (3) | 0.063 (5) | −0.017 (2) | 0.019 (3) | 0.004 (3) |
C24A | 0.037 (5) | 0.098 (10) | 0.062 (5) | −0.018 (5) | −0.002 (3) | 0.026 (5) |
C25A | 0.042 (3) | 0.067 (5) | 0.062 (3) | −0.011 (3) | −0.002 (2) | 0.017 (4) |
C26A | 0.037 (3) | 0.044 (4) | 0.045 (3) | −0.003 (2) | 0.007 (2) | 0.013 (3) |
C21B | 0.041 (4) | 0.034 (4) | 0.024 (4) | 0.006 (3) | 0.007 (2) | −0.001 (2) |
C22B | 0.041 (3) | 0.077 (6) | 0.045 (4) | −0.014 (3) | 0.019 (2) | 0.008 (3) |
C23B | 0.055 (4) | 0.077 (6) | 0.072 (6) | −0.014 (3) | 0.021 (4) | 0.018 (5) |
C24B | 0.035 (5) | 0.064 (7) | 0.096 (8) | −0.023 (4) | 0.010 (4) | 0.006 (5) |
C25B | 0.039 (3) | 0.067 (5) | 0.064 (3) | −0.009 (3) | −0.005 (2) | 0.020 (4) |
C26B | 0.037 (3) | 0.058 (5) | 0.048 (4) | −0.008 (3) | 0.008 (2) | 0.011 (3) |
Geometric parameters (Å, º) top
O01—C01 | 1.427 (2) | C12—H12B | 0.99 |
O02—C02 | 1.430 (2) | C13—H13A | 0.99 |
C01—C02 | 1.524 (2) | C13—H13B | 0.99 |
C01—C11 | 1.528 (2) | C14—H14A | 0.99 |
C11—C12 | 1.528 (2) | C14—H14B | 0.99 |
C11—C16 | 1.519 (2) | C15—H15A | 0.99 |
C12—C13 | 1.519 (2) | C15—H15B | 0.99 |
C13—C14 | 1.507 (2) | C16—H16A | 0.99 |
C14—C15 | 1.518 (3) | C16—H16B | 0.99 |
C15—C16 | 1.527 (2) | C21A—H21A | 1.00 |
C02—C21A | 1.602 (12) | C21B—H21B | 1.00 |
C02—C21B | 1.463 (13) | C22A—H22A | 0.99 |
C21A—C22A | 1.534 (9) | C22A—H22B | 0.99 |
C21A—C26A | 1.529 (10) | C22B—H22C | 0.99 |
C22A—C23A | 1.518 (9) | C22B—H22D | 0.99 |
C23A—C24A | 1.492 (10) | C23A—H23A | 0.99 |
C24A—C25A | 1.535 (10) | C23A—H23B | 0.99 |
C25A—C26A | 1.524 (9) | C23B—H23C | 0.99 |
C21B—C22B | 1.519 (10) | C23B—H23D | 0.99 |
C21B—C26B | 1.533 (9) | C24A—H24A | 0.99 |
C22B—C23B | 1.525 (10) | C24A—H24B | 0.99 |
C23B—C24B | 1.501 (10) | C24B—H24C | 0.99 |
C24B—C25B | 1.564 (11) | C24B—H24D | 0.99 |
C25B—C26B | 1.533 (9) | C25A—H25A | 0.99 |
O01—H91A | 0.85 (2) | C25A—H25B | 0.99 |
O01—H91B | 0.85 (2) | C25B—H25C | 0.99 |
O02—H92A | 0.84 (2) | C25B—H25D | 0.99 |
O02—H92B | 0.84 (2) | C26A—H26A | 0.99 |
C01—H01 | 0.96 | C26A—H26B | 0.99 |
C02—H02 | 0.97 | C26B—H26C | 0.99 |
C11—H11 | 1.00 | C26B—H26D | 0.99 |
C12—H12A | 0.99 | | |
| | | |
O01—C01—C02 | 107.89 (11) | C11—C16—H16B | 109.1 |
O01—C01—C11 | 110.90 (11) | C15—C16—H16A | 109.1 |
C02—C01—C11 | 114.18 (10) | C15—C16—H16B | 109.1 |
O02—C02—C01 | 107.79 (11) | C02—C21A—H21A | 109.6 |
O02—C02—C21A | 113.7 (4) | C22A—C21A—H21A | 109.6 |
O02—C02—C21B | 108.1 (4) | C26A—C21A—H21A | 109.6 |
C01—C02—C21A | 111.2 (4) | C02—C21B—H21B | 106.0 |
C01—C02—C21B | 118.2 (5) | C22B—C21B—H21B | 106.0 |
C01—C11—C12 | 111.40 (11) | C26B—C21B—H21B | 106.0 |
C01—C11—C16 | 112.36 (11) | C21A—C22A—H22A | 109.5 |
C12—C11—C16 | 110.30 (12) | C21A—C22A—H22B | 109.5 |
C11—C12—C13 | 112.38 (12) | C23A—C22A—H22A | 109.5 |
C12—C13—C14 | 111.23 (14) | C23A—C22A—H22B | 109.5 |
C13—C14—C15 | 110.51 (14) | C21B—C22B—H22C | 109.2 |
C14—C15—C16 | 112.05 (14) | C21B—C22B—H22D | 109.2 |
C11—C16—C15 | 112.38 (13) | C23B—C22B—H22C | 109.2 |
C02—C21A—C22A | 109.8 (9) | C23B—C22B—H22D | 109.2 |
C02—C21A—C26A | 109.5 (8) | C22A—C23A—H23A | 109.1 |
C22A—C21A—C26A | 108.6 (8) | C22A—C23A—H23B | 109.1 |
C21A—C22A—C23A | 110.6 (8) | C24A—C23A—H23A | 109.1 |
C22A—C23A—C24A | 112.6 (9) | C24A—C23A—H23B | 109.1 |
C23A—C24A—C25A | 113.7 (9) | C22B—C23B—H23C | 109.5 |
C24A—C25A—C26A | 112.9 (8) | C22B—C23B—H23D | 109.5 |
C21A—C26A—C25A | 112.3 (8) | C24B—C23B—H23C | 109.5 |
C02—C21B—C22B | 114.7 (10) | C24B—C23B—H23D | 109.5 |
C02—C21B—C26B | 112.6 (8) | C23A—C24A—H24A | 108.8 |
C22B—C21B—C26B | 110.9 (8) | C23A—C24A—H24B | 108.8 |
C21B—C22B—C23B | 112.3 (9) | C25A—C24A—H24A | 108.8 |
C22B—C23B—C24B | 110.7 (10) | C25A—C24A—H24B | 108.8 |
C23B—C24B—C25B | 108.3 (9) | C23B—C24B—H24C | 110.0 |
C24B—C25B—C26B | 108.7 (8) | C23B—C24B—H24D | 110.0 |
C21B—C26B—C25B | 112.1 (8) | C25B—C24B—H24C | 110.0 |
C01—O01—H91A | 119 (2) | C25B—C24B—H24D | 110.0 |
C01—O01—H91B | 118 (3) | C24A—C25A—H25A | 109.0 |
H91A—O01—H91B | 107 (3) | C24A—C25A—H25B | 109.0 |
C02—O02—H92A | 114 (2) | C26A—C25A—H25A | 109.0 |
C02—O02—H92B | 137 (3) | C26A—C25A—H25B | 109.0 |
H92A—O02—H92B | 95 (3) | C24B—C25B—H25C | 110.0 |
O01—C01—H01 | 105.1 | C24B—C25B—H25D | 110.0 |
C02—C01—H01 | 109.2 | C26B—C25B—H25C | 110.0 |
C11—C01—H01 | 109.1 | C26B—C25B—H25D | 110.0 |
O02—C02—H02 | 107.3 | C21A—C26A—H26A | 109.1 |
C01—C02—H02 | 108.7 | C21A—C26A—H26B | 109.1 |
C21A—C02—H02 | 108.0 | C25A—C26A—H26A | 109.1 |
C21B—C02—H02 | 106.4 | C25A—C26A—H26B | 109.1 |
C01—C11—H11 | 107.5 | C21B—C26B—H26C | 109.2 |
C12—C11—H11 | 107.5 | C21B—C26B—H26D | 109.2 |
C16—C11—H11 | 107.5 | C25B—C26B—H26C | 109.2 |
C11—C12—H12A | 109.1 | C25B—C26B—H26D | 109.2 |
C11—C12—H12B | 109.1 | H12A—C12—H12B | 107.9 |
C13—C12—H12A | 109.1 | H13A—C13—H13B | 108.0 |
C13—C12—H12B | 109.1 | H14A—C14—H14B | 108.1 |
C12—C13—H13A | 109.4 | H15A—C15—H15B | 107.9 |
C12—C13—H13B | 109.4 | H16A—C16—H16B | 107.9 |
C14—C13—H13A | 109.4 | H22A—C22A—H22B | 108.1 |
C14—C13—H13B | 109.4 | H22C—C22B—H22D | 107.9 |
C13—C14—H14A | 109.5 | H23A—C23A—H23B | 107.8 |
C13—C14—H14B | 109.5 | H23C—C23B—H23D | 108.1 |
C15—C14—H14A | 109.5 | H24A—C24A—H24B | 107.7 |
C15—C14—H14B | 109.5 | H24C—C24B—H24D | 108.4 |
C14—C15—H15A | 109.2 | H25A—C25A—H25B | 107.8 |
C14—C15—H15B | 109.2 | H25C—C25B—H25D | 108.3 |
C16—C15—H15A | 109.2 | H26A—C26A—H26B | 107.9 |
C16—C15—H15B | 109.2 | H26C—C26B—H26D | 107.9 |
C11—C16—H16A | 109.1 | | |
| | | |
O01—C01—C02—O02 | −73.24 (14) | C01—C02—C21A—C22A | −168.1 (7) |
C11—C01—C02—O02 | 50.53 (16) | C26A—C21A—C22A—C23A | −60.2 (12) |
O01—C01—C02—C21B | 49.5 (6) | C02—C21A—C22A—C23A | −179.9 (8) |
C11—C01—C02—C21B | 173.3 (5) | C21A—C22A—C23A—C24A | 57.2 (13) |
O01—C01—C02—C21A | 52.0 (5) | C22A—C23A—C24A—C25A | −49.4 (16) |
C11—C01—C02—C21A | 175.8 (5) | C23A—C24A—C25A—C26A | 45.8 (16) |
O01—C01—C11—C16 | 179.55 (11) | C24A—C25A—C26A—C21A | −50.3 (12) |
C02—C01—C11—C16 | 57.41 (16) | C22A—C21A—C26A—C25A | 57.3 (12) |
O01—C01—C11—C12 | −56.11 (16) | C02—C21A—C26A—C25A | 177.2 (8) |
C02—C01—C11—C12 | −178.25 (12) | O02—C02—C21B—C22B | −58.3 (10) |
C16—C11—C12—C13 | −53.85 (18) | C01—C02—C21B—C22B | 179.0 (7) |
C01—C11—C12—C13 | −179.34 (13) | O02—C02—C21B—C26B | 173.6 (7) |
C11—C12—C13—C14 | 56.57 (19) | C01—C02—C21B—C26B | 51.0 (10) |
C12—C13—C14—C15 | −56.27 (19) | C02—C21B—C22B—C23B | 179.2 (9) |
C13—C14—C15—C16 | 55.2 (2) | C26B—C21B—C22B—C23B | −51.9 (14) |
C12—C11—C16—C15 | 52.32 (18) | C21B—C22B—C23B—C24B | 57.9 (13) |
C01—C11—C16—C15 | 177.26 (13) | C22B—C23B—C24B—C25B | −61.7 (14) |
C14—C15—C16—C11 | −54.0 (2) | C23B—C24B—C25B—C26B | 61.4 (13) |
O02—C02—C21A—C26A | −165.4 (6) | C24B—C25B—C26B—C21B | −57.4 (10) |
C21B—C02—C21A—C26A | −125 (8) | C02—C21B—C26B—C25B | −177.2 (8) |
C01—C02—C21A—C26A | 72.7 (9) | C22B—C21B—C26B—C25B | 52.8 (12) |
O02—C02—C21A—C22A | −46.3 (10) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O01—H91A···O01i | 0.85 (2) | 1.85 (2) | 2.652 (2) | 155 (3) |
O01—H91B···O02ii | 0.85 (2) | 1.93 (2) | 2.665 (2) | 145 (3) |
O02—H92A···O02iii | 0.84 (2) | 1.81 (2) | 2.636 (2) | 166 (4) |
O02—H92B···O01ii | 0.84 (2) | 1.83 (2) | 2.665 (2) | 170 (4) |
Symmetry codes: (i) −x, y, −z+1/2; (ii) −x, −y+2, −z; (iii) −x, y, −z−1/2. |
Experimental details
| (k98005) | (k00009) | (k98064) | (k00013) |
Crystal data |
Chemical formula | C14H26O2 | C14H26O2 | C14H26O2 | C14H26O2 |
Mr | 226.35 | 226.35 | 226.35 | 226.35 |
Crystal system, space group | Monoclinic, P1211 | Monoclinic, P1211 | Monoclinic, C12/c1 | Monoclinic, C12/c1 |
Temperature (K) | 295 | 173 | 295 | 173 |
a, b, c (Å) | 5.540 (1), 41.653 (6), 12.025 (2) | 5.4816 (6), 41.262 (6), 11.954 (2) | 23.153 (5), 11.852 (3), 10.926 (2) | 23.161 (5), 11.584 (3), 10.973 (2) |
β (°) | 90.33 (1) | 90.39 (1) | 104.64 (2) | 106.10 (2) |
V (Å3) | 2774.8 (8) | 2703.7 (7) | 2900.9 (11) | 2828.6 (11) |
Z | 8 | 8 | 8 | 8 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.07 | 0.07 | 0.07 | 0.07 |
Crystal size (mm) | 0.50 × 0.32 × 0.25 | 0.44 × 0.20 × 0.16 | 0.31 × 0.22 × 0.13 | 0.56 × 0.55 × 0.10 |
|
Data collection |
Diffractometer | Nonius Kappa-CCD diffractometer | Nonius Kappa-CCD diffractometer | Nonius Kappa-CCD diffractometer | Nonius Kappa-CCD diffractometer |
Absorption correction | – | – | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9310, 4928, 3636 | 8305, 4720, 3750 | 4869, 2529, 1942 | 4693, 2489, 1911 |
Rint | 0.047 | 0.034 | 0.023 | 0.021 |
(sin θ/λ)max (Å−1) | 0.595 | 0.595 | 0.595 | 0.595 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.144, 1.09 | 0.042, 0.089, 1.03 | 0.068, 0.208, 1.13 | 0.047, 0.118, 1.06 |
No. of reflections | 4928 | 4720 | 2529 | 2489 |
No. of parameters | 610 | 609 | 211 | 211 |
No. of restraints | 1 | 1 | 64 | 64 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.11 | 0.12, −0.15 | 0.14, −0.12 | 0.15, −0.19 |
Hydrogen-bond geometry (Å, º) for (k98005) top
D—H···A | D—H | H···A | D···A | D—H···A |
O01A—H01A···O02Ai | 1.01 (8) | 1.76 (8) | 2.760 (4) | 174 (6) |
O01B—H01B···O02Bii | 0.73 (4) | 1.98 (5) | 2.704 (4) | 168 (4) |
O01C—H01C···O02Ci | 0.82 (5) | 1.95 (5) | 2.759 (4) | 167 (4) |
O01D—H01D···O02Dii | 0.83 (5) | 1.86 (5) | 2.682 (4) | 176 (5) |
O02A—H02A···O01B | 0.79 (6) | 1.95 (6) | 2.717 (5) | 163 (6) |
O02B—H02B···O01A | 0.81 (5) | 1.98 (5) | 2.746 (5) | 158 (4) |
O02C—H02C···O01D | 0.87 (6) | 1.90 (6) | 2.725 (5) | 158 (5) |
O02D—H02D···O01C | 0.72 (6) | 2.15 (6) | 2.731 (5) | 140 (6) |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
Hydrogen-bond geometry (Å, º) for (k00009) top
D—H···A | D—H | H···A | D···A | D—H···A |
O01A—H01A···O02Ai | 0.90 (4) | 1.83 (4) | 2.724 (2) | 170 (4) |
O01B—H01B···O02Bii | 0.95 (3) | 1.72 (3) | 2.656 (3) | 169 (3) |
O01C—H01C···O02Ci | 0.93 (4) | 1.80 (4) | 2.730 (2) | 172 (3) |
O01D—H01D···O02Dii | 0.85 (3) | 1.81 (3) | 2.658 (3) | 174 (3) |
O02A—H02A···O01B | 1.05 (5) | 1.66 (5) | 2.682 (3) | 161 (4) |
O02B—H02B···O01A | 0.95 (4) | 1.87 (4) | 2.727 (3) | 149 (3) |
O02C—H02C···O01D | 0.97 (4) | 1.78 (4) | 2.698 (3) | 157 (3) |
O02D—H02D···O01C | 0.91 (5) | 1.88 (5) | 2.717 (3) | 152 (4) |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
Hydrogen-bond geometry (Å, º) for (k98064) top
D—H···A | D—H | H···A | D···A | D—H···A |
O01—H91A···O01i | 0.84 (2) | 1.87 (2) | 2.641 (3) | 152 (5) |
O01—H91B···O02ii | 0.84 (2) | 1.91 (3) | 2.682 (3) | 153 (6) |
O02—H92A···O02iii | 0.83 (2) | 1.86 (2) | 2.654 (3) | 160 (5) |
O02—H92B···O01ii | 0.84 (2) | 2.01 (4) | 2.682 (3) | 138 (5) |
Symmetry codes: (i) −x, y, −z+1/2; (ii) −x, −y+2, −z; (iii) −x, y, −z−1/2. |
Hydrogen-bond geometry (Å, º) for (k00013) top
D—H···A | D—H | H···A | D···A | D—H···A |
O01—H91A···O01i | 0.85 (2) | 1.85 (2) | 2.652 (2) | 155 (3) |
O01—H91B···O02ii | 0.85 (2) | 1.93 (2) | 2.665 (2) | 145 (3) |
O02—H92A···O02iii | 0.84 (2) | 1.81 (2) | 2.636 (2) | 166 (4) |
O02—H92B···O01ii | 0.84 (2) | 1.83 (2) | 2.665 (2) | 170 (4) |
Symmetry codes: (i) −x, y, −z+1/2; (ii) −x, −y+2, −z; (iii) −x, y, −z−1/2. |