Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806013936/ob2014sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806013936/ob2014Isup2.hkl |
CCDC reference: 608467
Data collection: APEX2 (Bruker Nonius, 2004); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C7H16O | Z = 8 |
Mr = 116.20 | F(000) = 528 |
Triclinic, P1 | Dx = 0.992 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.5552 (10) Å | Cell parameters from 5406 reflections |
b = 11.2140 (9) Å | θ = 2.2–25.7° |
c = 14.1681 (13) Å | µ = 0.06 mm−1 |
α = 88.682 (3)° | T = 150 K |
β = 72.512 (3)° | Cylinder, colourless |
γ = 76.904 (4)° | 0.60 × 0.20 (radius) mm |
V = 1556.1 (2) Å3 |
Bruker–Nonius X8APEX-II CCD diffractometer | 5870 independent reflections |
Radiation source: fine-focus sealed tube | 4402 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
ω and φ scans | θmax = 25.8°, θmin = 3.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003); ratio of minimum to maximum apparent transmission: 0.711045 | h = −12→12 |
Tmin = 0.693, Tmax = 0.975 | k = −13→13 |
35248 measured reflections | l = −17→16 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0499P)2 + 0.3995P] where P = (Fo2 + 2Fc2)/3 |
5870 reflections | (Δ/σ)max < 0.001 |
305 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Experimental. Grown in situ in 0.4 mm o.d. capillary at 258 K. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.40289 (12) | 0.90260 (9) | 0.77740 (7) | 0.0315 (2) | |
H1 | 0.488 (2) | 0.8898 (17) | 0.7602 (14) | 0.053 (6)* | |
C1 | 0.34684 (14) | 0.99578 (13) | 0.85685 (11) | 0.0298 (3) | |
C11 | 0.19371 (14) | 1.02633 (14) | 0.87228 (11) | 0.0334 (3) | |
H11A | 0.1773 | 1.0547 | 0.8094 | 0.040* | |
H11B | 0.1602 | 0.9503 | 0.8877 | 0.040* | |
C12 | 0.11041 (17) | 1.12344 (17) | 0.95413 (14) | 0.0504 (5) | |
H12A | 0.0135 | 1.1369 | 0.9594 | 0.076* | |
H12B | 0.1401 | 1.2002 | 0.9385 | 0.076* | |
H12C | 0.1241 | 1.0957 | 1.0172 | 0.076* | |
C13 | 0.38380 (17) | 0.94505 (16) | 0.94897 (12) | 0.0428 (4) | |
H13A | 0.4845 | 0.9206 | 0.9317 | 0.051* | |
H13B | 0.3518 | 1.0122 | 1.0007 | 0.051* | |
C14 | 0.3269 (2) | 0.83686 (17) | 0.99320 (13) | 0.0529 (5) | |
H14A | 0.3563 | 0.8127 | 1.0516 | 0.079* | |
H14B | 0.3606 | 0.7680 | 0.9440 | 0.079* | |
H14C | 0.2270 | 0.8599 | 1.0126 | 0.079* | |
C15 | 0.41021 (17) | 1.10562 (14) | 0.82482 (14) | 0.0461 (4) | |
H15A | 0.3728 | 1.1689 | 0.8798 | 0.055* | |
H15B | 0.5098 | 1.0790 | 0.8139 | 0.055* | |
C16 | 0.38705 (19) | 1.16378 (16) | 0.73209 (16) | 0.0631 (6) | |
H16A | 0.4306 | 1.2334 | 0.7178 | 0.095* | |
H16B | 0.2888 | 1.1924 | 0.7422 | 0.095* | |
H16C | 0.4268 | 1.1032 | 0.6762 | 0.095* | |
O2 | 0.38796 (10) | 0.65997 (10) | 0.76864 (7) | 0.0297 (2) | |
H2 | 0.3789 (18) | 0.7372 (18) | 0.7787 (13) | 0.052 (5)* | |
C2 | 0.29072 (13) | 0.64111 (12) | 0.72043 (10) | 0.0253 (3) | |
C21 | 0.34258 (15) | 0.50924 (13) | 0.67860 (12) | 0.0331 (3) | |
H21A | 0.3451 | 0.4544 | 0.7341 | 0.040* | |
H21B | 0.4374 | 0.4991 | 0.6346 | 0.040* | |
C22 | 0.25841 (17) | 0.46803 (15) | 0.62060 (12) | 0.0396 (4) | |
H22A | 0.2990 | 0.3825 | 0.5966 | 0.059* | |
H22B | 0.2573 | 0.5199 | 0.5641 | 0.059* | |
H22C | 0.1648 | 0.4751 | 0.6638 | 0.059* | |
C23 | 0.15020 (15) | 0.66230 (14) | 0.79861 (11) | 0.0322 (3) | |
H23A | 0.1239 | 0.7485 | 0.8245 | 0.039* | |
H23B | 0.0828 | 0.6511 | 0.7657 | 0.039* | |
C24 | 0.14012 (19) | 0.57976 (17) | 0.88572 (12) | 0.0484 (4) | |
H24A | 0.0470 | 0.6006 | 0.9314 | 0.073* | |
H24B | 0.2044 | 0.5914 | 0.9203 | 0.073* | |
H24C | 0.1625 | 0.4940 | 0.8616 | 0.073* | |
C25 | 0.28532 (15) | 0.73408 (14) | 0.64017 (11) | 0.0318 (3) | |
H25A | 0.2180 | 0.7209 | 0.6080 | 0.038* | |
H25B | 0.2520 | 0.8175 | 0.6723 | 0.038* | |
C26 | 0.42064 (18) | 0.72830 (18) | 0.56046 (12) | 0.0469 (4) | |
H26A | 0.4080 | 0.7906 | 0.5124 | 0.070* | |
H26B | 0.4535 | 0.6469 | 0.5266 | 0.070* | |
H26C | 0.4877 | 0.7437 | 0.5910 | 0.070* | |
O3 | 0.66917 (11) | 0.58633 (9) | 0.72772 (7) | 0.0311 (2) | |
H3 | 0.581 (2) | 0.5997 (17) | 0.7388 (14) | 0.053 (6)* | |
C3 | 0.71170 (14) | 0.48503 (12) | 0.78489 (10) | 0.0265 (3) | |
C31 | 0.66539 (15) | 0.37452 (13) | 0.75734 (11) | 0.0321 (3) | |
H31A | 0.6916 | 0.3056 | 0.7978 | 0.039* | |
H31B | 0.5645 | 0.3956 | 0.7751 | 0.039* | |
C32 | 0.72343 (18) | 0.33130 (15) | 0.64872 (12) | 0.0417 (4) | |
H32A | 0.6879 | 0.2610 | 0.6378 | 0.063* | |
H32B | 0.8232 | 0.3070 | 0.6306 | 0.063* | |
H32C | 0.6965 | 0.3980 | 0.6077 | 0.063* | |
C33 | 0.86688 (14) | 0.46344 (13) | 0.75528 (11) | 0.0307 (3) | |
H33A | 0.9041 | 0.4479 | 0.6826 | 0.037* | |
H33B | 0.8906 | 0.5392 | 0.7718 | 0.037* | |
C34 | 0.93606 (16) | 0.35711 (15) | 0.80487 (13) | 0.0437 (4) | |
H34A | 1.0350 | 0.3494 | 0.7819 | 0.066* | |
H34B | 0.9154 | 0.2810 | 0.7877 | 0.066* | |
H34C | 0.9022 | 0.3726 | 0.8769 | 0.066* | |
C35 | 0.64336 (16) | 0.51971 (14) | 0.89532 (11) | 0.0362 (4) | |
H35A | 0.5432 | 0.5391 | 0.9082 | 0.043* | |
H35B | 0.6671 | 0.4473 | 0.9333 | 0.043* | |
C36 | 0.6810 (2) | 0.62704 (17) | 0.93451 (13) | 0.0518 (5) | |
H36A | 0.6319 | 0.6423 | 1.0053 | 0.078* | |
H36B | 0.6560 | 0.7001 | 0.8988 | 0.078* | |
H36C | 0.7795 | 0.6081 | 0.9247 | 0.078* | |
O4 | 0.68743 (11) | 0.82986 (10) | 0.70223 (8) | 0.0378 (3) | |
H4 | 0.7007 (18) | 0.7555 (18) | 0.7003 (13) | 0.047 (5)* | |
C4 | 0.78629 (14) | 0.87387 (12) | 0.62269 (11) | 0.0292 (3) | |
C41 | 0.92051 (14) | 0.77709 (12) | 0.59159 (11) | 0.0301 (3) | |
H41A | 0.9924 | 0.8160 | 0.5502 | 0.036* | |
H41B | 0.9458 | 0.7505 | 0.6519 | 0.036* | |
C42 | 0.92080 (17) | 0.66394 (14) | 0.53459 (12) | 0.0396 (4) | |
H42A | 1.0110 | 0.6078 | 0.5188 | 0.059* | |
H42B | 0.8998 | 0.6882 | 0.4731 | 0.059* | |
H42C | 0.8518 | 0.6229 | 0.5751 | 0.059* | |
C43 | 0.72389 (16) | 0.90298 (15) | 0.53814 (13) | 0.0425 (4) | |
H43A | 0.6372 | 0.9655 | 0.5631 | 0.051* | |
H43B | 0.7014 | 0.8279 | 0.5188 | 0.051* | |
C44 | 0.8139 (2) | 0.94965 (18) | 0.44555 (14) | 0.0573 (5) | |
H44A | 0.7659 | 0.9651 | 0.3955 | 0.086* | |
H44B | 0.8994 | 0.8878 | 0.4189 | 0.086* | |
H44C | 0.8342 | 1.0259 | 0.4629 | 0.086* | |
C45 | 0.80438 (17) | 0.99005 (14) | 0.66552 (13) | 0.0424 (4) | |
H45A | 0.8663 | 1.0269 | 0.6122 | 0.051* | |
H45B | 0.7147 | 1.0492 | 0.6864 | 0.051* | |
C46 | 0.8607 (2) | 0.97319 (19) | 0.75291 (14) | 0.0628 (6) | |
H46A | 0.8679 | 1.0527 | 0.7753 | 0.094* | |
H46B | 0.9513 | 0.9174 | 0.7327 | 0.094* | |
H46C | 0.7994 | 0.9386 | 0.8071 | 0.094* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0303 (6) | 0.0278 (5) | 0.0322 (6) | −0.0060 (4) | −0.0034 (5) | −0.0066 (4) |
C1 | 0.0257 (8) | 0.0273 (7) | 0.0327 (8) | −0.0057 (6) | −0.0029 (6) | −0.0092 (6) |
C11 | 0.0265 (8) | 0.0367 (8) | 0.0351 (8) | −0.0081 (6) | −0.0062 (6) | 0.0022 (7) |
C12 | 0.0323 (9) | 0.0503 (10) | 0.0532 (11) | 0.0023 (8) | 0.0014 (8) | −0.0036 (9) |
C13 | 0.0316 (9) | 0.0560 (10) | 0.0388 (9) | −0.0024 (7) | −0.0123 (7) | −0.0141 (8) |
C14 | 0.0586 (12) | 0.0625 (12) | 0.0329 (9) | −0.0048 (9) | −0.0140 (8) | 0.0081 (8) |
C15 | 0.0339 (9) | 0.0324 (9) | 0.0615 (11) | −0.0121 (7) | 0.0057 (8) | −0.0159 (8) |
C16 | 0.0469 (11) | 0.0330 (9) | 0.0889 (15) | −0.0095 (8) | 0.0091 (10) | 0.0136 (9) |
O2 | 0.0303 (6) | 0.0266 (6) | 0.0365 (6) | −0.0073 (4) | −0.0155 (5) | −0.0004 (4) |
C2 | 0.0221 (7) | 0.0272 (7) | 0.0283 (7) | −0.0067 (6) | −0.0092 (6) | 0.0002 (6) |
C21 | 0.0305 (8) | 0.0300 (8) | 0.0392 (8) | −0.0061 (6) | −0.0113 (7) | −0.0039 (7) |
C22 | 0.0408 (9) | 0.0403 (9) | 0.0402 (9) | −0.0140 (7) | −0.0119 (7) | −0.0067 (7) |
C23 | 0.0293 (8) | 0.0365 (8) | 0.0312 (8) | −0.0106 (6) | −0.0074 (6) | 0.0003 (6) |
C24 | 0.0531 (11) | 0.0619 (11) | 0.0336 (9) | −0.0272 (9) | −0.0084 (8) | 0.0094 (8) |
C25 | 0.0321 (8) | 0.0344 (8) | 0.0316 (8) | −0.0114 (6) | −0.0113 (6) | 0.0052 (6) |
C26 | 0.0466 (10) | 0.0655 (11) | 0.0328 (9) | −0.0287 (9) | −0.0071 (8) | 0.0088 (8) |
O3 | 0.0265 (6) | 0.0279 (5) | 0.0344 (6) | −0.0045 (4) | −0.0046 (5) | 0.0107 (4) |
C3 | 0.0245 (7) | 0.0266 (7) | 0.0252 (7) | −0.0050 (6) | −0.0039 (6) | 0.0073 (6) |
C31 | 0.0306 (8) | 0.0309 (8) | 0.0356 (8) | −0.0100 (6) | −0.0099 (7) | 0.0114 (6) |
C32 | 0.0524 (10) | 0.0349 (8) | 0.0397 (9) | −0.0107 (7) | −0.0162 (8) | 0.0016 (7) |
C33 | 0.0256 (8) | 0.0328 (8) | 0.0307 (8) | −0.0063 (6) | −0.0044 (6) | 0.0037 (6) |
C34 | 0.0319 (9) | 0.0479 (10) | 0.0489 (10) | −0.0026 (7) | −0.0140 (8) | 0.0098 (8) |
C35 | 0.0311 (8) | 0.0421 (9) | 0.0282 (8) | −0.0041 (7) | −0.0019 (6) | 0.0037 (7) |
C36 | 0.0572 (12) | 0.0521 (11) | 0.0401 (10) | −0.0042 (9) | −0.0112 (8) | −0.0102 (8) |
O4 | 0.0337 (6) | 0.0272 (6) | 0.0410 (6) | −0.0097 (5) | 0.0077 (5) | 0.0038 (5) |
C4 | 0.0233 (7) | 0.0255 (7) | 0.0328 (8) | −0.0071 (6) | 0.0010 (6) | 0.0051 (6) |
C41 | 0.0267 (8) | 0.0292 (7) | 0.0293 (7) | −0.0037 (6) | −0.0030 (6) | 0.0014 (6) |
C42 | 0.0426 (9) | 0.0313 (8) | 0.0345 (8) | −0.0083 (7) | 0.0037 (7) | −0.0012 (7) |
C43 | 0.0307 (9) | 0.0434 (9) | 0.0524 (10) | −0.0089 (7) | −0.0120 (8) | 0.0162 (8) |
C44 | 0.0568 (12) | 0.0668 (12) | 0.0525 (11) | −0.0205 (10) | −0.0204 (9) | 0.0312 (10) |
C45 | 0.0359 (9) | 0.0276 (8) | 0.0511 (10) | −0.0082 (7) | 0.0063 (8) | −0.0041 (7) |
C46 | 0.0765 (14) | 0.0613 (12) | 0.0489 (11) | −0.0292 (11) | −0.0046 (10) | −0.0210 (10) |
O1—C1 | 1.4431 (17) | O3—C3 | 1.4468 (16) |
O1—H1 | 0.84 (2) | O3—H3 | 0.87 (2) |
C1—C11 | 1.523 (2) | C3—C33 | 1.5262 (19) |
C1—C15 | 1.528 (2) | C3—C31 | 1.529 (2) |
C1—C13 | 1.533 (2) | C3—C35 | 1.530 (2) |
C11—C12 | 1.522 (2) | C31—C32 | 1.520 (2) |
C11—H11A | 0.990 | C31—H31A | 0.990 |
C11—H11B | 0.990 | C31—H31B | 0.990 |
C12—H12A | 0.980 | C32—H32A | 0.980 |
C12—H12B | 0.980 | C32—H32B | 0.980 |
C12—H12C | 0.980 | C32—H32C | 0.980 |
C13—C14 | 1.515 (3) | C33—C34 | 1.524 (2) |
C13—H13A | 0.990 | C33—H33A | 0.990 |
C13—H13B | 0.990 | C33—H33B | 0.990 |
C14—H14A | 0.980 | C34—H34A | 0.980 |
C14—H14B | 0.980 | C34—H34B | 0.980 |
C14—H14C | 0.980 | C34—H34C | 0.980 |
C15—C16 | 1.514 (3) | C35—C36 | 1.515 (2) |
C15—H15A | 0.990 | C35—H35A | 0.990 |
C15—H15B | 0.990 | C35—H35B | 0.990 |
C16—H16A | 0.980 | C36—H36A | 0.980 |
C16—H16B | 0.980 | C36—H36B | 0.980 |
C16—H16C | 0.980 | C36—H36C | 0.980 |
O2—C2 | 1.4460 (16) | O4—C4 | 1.4503 (16) |
O2—H2 | 0.86 (2) | O4—H4 | 0.81 (2) |
C2—C21 | 1.5220 (19) | C4—C45 | 1.523 (2) |
C2—C25 | 1.5300 (19) | C4—C41 | 1.5262 (19) |
C2—C23 | 1.5324 (19) | C4—C43 | 1.528 (2) |
C21—C22 | 1.523 (2) | C41—C42 | 1.519 (2) |
C21—H21A | 0.990 | C41—H41A | 0.990 |
C21—H21B | 0.990 | C41—H41B | 0.990 |
C22—H22A | 0.980 | C42—H42A | 0.980 |
C22—H22B | 0.980 | C42—H42B | 0.980 |
C22—H22C | 0.980 | C42—H42C | 0.980 |
C23—C24 | 1.518 (2) | C43—C44 | 1.531 (2) |
C23—H23A | 0.990 | C43—H43A | 0.990 |
C23—H23B | 0.990 | C43—H43B | 0.990 |
C24—H24A | 0.980 | C44—H44A | 0.980 |
C24—H24B | 0.980 | C44—H44B | 0.980 |
C24—H24C | 0.980 | C44—H44C | 0.980 |
C25—C26 | 1.520 (2) | C45—C46 | 1.518 (3) |
C25—H25A | 0.990 | C45—H45A | 0.990 |
C25—H25B | 0.990 | C45—H45B | 0.990 |
C26—H26A | 0.980 | C46—H46A | 0.980 |
C26—H26B | 0.980 | C46—H46B | 0.980 |
C26—H26C | 0.980 | C46—H46C | 0.980 |
C1—O1—H1 | 108.7 (13) | C3—O3—H3 | 109.1 (12) |
O1—C1—C11 | 104.77 (11) | O3—C3—C33 | 105.04 (10) |
O1—C1—C15 | 108.55 (12) | O3—C3—C31 | 108.10 (11) |
C11—C1—C15 | 112.51 (13) | C33—C3—C31 | 112.32 (12) |
O1—C1—C13 | 109.24 (12) | O3—C3—C35 | 109.22 (11) |
C11—C1—C13 | 112.74 (12) | C33—C3—C35 | 112.66 (12) |
C15—C1—C13 | 108.86 (13) | C31—C3—C35 | 109.31 (11) |
C12—C11—C1 | 114.86 (13) | C32—C31—C3 | 115.09 (12) |
C12—C11—H11A | 108.6 | C32—C31—H31A | 108.5 |
C1—C11—H11A | 108.6 | C3—C31—H31A | 108.5 |
C12—C11—H11B | 108.6 | C32—C31—H31B | 108.5 |
C1—C11—H11B | 108.6 | C3—C31—H31B | 108.5 |
H11A—C11—H11B | 107.5 | H31A—C31—H31B | 107.5 |
C11—C12—H12A | 109.5 | C31—C32—H32A | 109.5 |
C11—C12—H12B | 109.5 | C31—C32—H32B | 109.5 |
H12A—C12—H12B | 109.5 | H32A—C32—H32B | 109.5 |
C11—C12—H12C | 109.5 | C31—C32—H32C | 109.5 |
H12A—C12—H12C | 109.5 | H32A—C32—H32C | 109.5 |
H12B—C12—H12C | 109.5 | H32B—C32—H32C | 109.5 |
C14—C13—C1 | 116.52 (13) | C34—C33—C3 | 114.61 (12) |
C14—C13—H13A | 108.2 | C34—C33—H33A | 108.6 |
C1—C13—H13A | 108.2 | C3—C33—H33A | 108.6 |
C14—C13—H13B | 108.2 | C34—C33—H33B | 108.6 |
C1—C13—H13B | 108.2 | C3—C33—H33B | 108.6 |
H13A—C13—H13B | 107.3 | H33A—C33—H33B | 107.6 |
C13—C14—H14A | 109.5 | C33—C34—H34A | 109.5 |
C13—C14—H14B | 109.5 | C33—C34—H34B | 109.5 |
H14A—C14—H14B | 109.5 | H34A—C34—H34B | 109.5 |
C13—C14—H14C | 109.5 | C33—C34—H34C | 109.5 |
H14A—C14—H14C | 109.5 | H34A—C34—H34C | 109.5 |
H14B—C14—H14C | 109.5 | H34B—C34—H34C | 109.5 |
C16—C15—C1 | 115.38 (15) | C36—C35—C3 | 115.64 (13) |
C16—C15—H15A | 108.4 | C36—C35—H35A | 108.4 |
C1—C15—H15A | 108.4 | C3—C35—H35A | 108.4 |
C16—C15—H15B | 108.4 | C36—C35—H35B | 108.4 |
C1—C15—H15B | 108.4 | C3—C35—H35B | 108.4 |
H15A—C15—H15B | 107.5 | H35A—C35—H35B | 107.4 |
C15—C16—H16A | 109.5 | C35—C36—H36A | 109.5 |
C15—C16—H16B | 109.5 | C35—C36—H36B | 109.5 |
H16A—C16—H16B | 109.5 | H36A—C36—H36B | 109.5 |
C15—C16—H16C | 109.5 | C35—C36—H36C | 109.5 |
H16A—C16—H16C | 109.5 | H36A—C36—H36C | 109.5 |
H16B—C16—H16C | 109.5 | H36B—C36—H36C | 109.5 |
C2—O2—H2 | 109.7 (12) | C4—O4—H4 | 112.5 (13) |
O2—C2—C21 | 105.01 (11) | O4—C4—C45 | 105.39 (11) |
O2—C2—C25 | 109.17 (11) | O4—C4—C41 | 109.70 (11) |
C21—C2—C25 | 112.82 (12) | C45—C4—C41 | 111.04 (12) |
O2—C2—C23 | 108.01 (11) | O4—C4—C43 | 107.13 (12) |
C21—C2—C23 | 112.38 (12) | C45—C4—C43 | 110.84 (12) |
C25—C2—C23 | 109.24 (11) | C41—C4—C43 | 112.41 (12) |
C2—C21—C22 | 115.05 (12) | C42—C41—C4 | 116.06 (13) |
C2—C21—H21A | 108.5 | C42—C41—H41A | 108.3 |
C22—C21—H21A | 108.5 | C4—C41—H41A | 108.3 |
C2—C21—H21B | 108.5 | C42—C41—H41B | 108.3 |
C22—C21—H21B | 108.5 | C4—C41—H41B | 108.3 |
H21A—C21—H21B | 107.5 | H41A—C41—H41B | 107.4 |
C21—C22—H22A | 109.5 | C41—C42—H42A | 109.5 |
C21—C22—H22B | 109.5 | C41—C42—H42B | 109.5 |
H22A—C22—H22B | 109.5 | H42A—C42—H42B | 109.5 |
C21—C22—H22C | 109.5 | C41—C42—H42C | 109.5 |
H22A—C22—H22C | 109.5 | H42A—C42—H42C | 109.5 |
H22B—C22—H22C | 109.5 | H42B—C42—H42C | 109.5 |
C24—C23—C2 | 115.67 (13) | C4—C43—C44 | 115.36 (13) |
C24—C23—H23A | 108.4 | C4—C43—H43A | 108.4 |
C2—C23—H23A | 108.4 | C44—C43—H43A | 108.4 |
C24—C23—H23B | 108.4 | C4—C43—H43B | 108.4 |
C2—C23—H23B | 108.4 | C44—C43—H43B | 108.4 |
H23A—C23—H23B | 107.4 | H43A—C43—H43B | 107.5 |
C23—C24—H24A | 109.5 | C43—C44—H44A | 109.5 |
C23—C24—H24B | 109.5 | C43—C44—H44B | 109.5 |
H24A—C24—H24B | 109.5 | H44A—C44—H44B | 109.5 |
C23—C24—H24C | 109.5 | C43—C44—H44C | 109.5 |
H24A—C24—H24C | 109.5 | H44A—C44—H44C | 109.5 |
H24B—C24—H24C | 109.5 | H44B—C44—H44C | 109.5 |
C26—C25—C2 | 114.90 (13) | C46—C45—C4 | 115.63 (14) |
C26—C25—H25A | 108.5 | C46—C45—H45A | 108.4 |
C2—C25—H25A | 108.5 | C4—C45—H45A | 108.4 |
C26—C25—H25B | 108.5 | C46—C45—H45B | 108.4 |
C2—C25—H25B | 108.5 | C4—C45—H45B | 108.4 |
H25A—C25—H25B | 107.5 | H45A—C45—H45B | 107.4 |
C25—C26—H26A | 109.5 | C45—C46—H46A | 109.5 |
C25—C26—H26B | 109.5 | C45—C46—H46B | 109.5 |
H26A—C26—H26B | 109.5 | H46A—C46—H46B | 109.5 |
C25—C26—H26C | 109.5 | C45—C46—H46C | 109.5 |
H26A—C26—H26C | 109.5 | H46A—C46—H46C | 109.5 |
H26B—C26—H26C | 109.5 | H46B—C46—H46C | 109.5 |
O1—C1—C11—C12 | 179.62 (12) | O3—C3—C31—C32 | 60.06 (16) |
C15—C1—C11—C12 | −62.65 (18) | C33—C3—C31—C32 | −55.35 (16) |
C13—C1—C11—C12 | 60.93 (17) | C35—C3—C31—C32 | 178.84 (13) |
O1—C1—C13—C14 | −62.97 (17) | O3—C3—C33—C34 | −178.48 (12) |
C11—C1—C13—C14 | 53.08 (18) | C31—C3—C33—C34 | −61.23 (17) |
C15—C1—C13—C14 | 178.65 (14) | C35—C3—C33—C34 | 62.74 (17) |
O1—C1—C15—C16 | 59.15 (17) | O3—C3—C35—C36 | −62.85 (17) |
C11—C1—C15—C16 | −56.33 (18) | C33—C3—C35—C36 | 53.46 (17) |
C13—C1—C15—C16 | 177.96 (13) | C31—C3—C35—C36 | 179.07 (13) |
O2—C2—C21—C22 | −178.14 (12) | O4—C4—C41—C42 | 72.21 (16) |
C25—C2—C21—C22 | −59.35 (17) | C45—C4—C41—C42 | −171.70 (12) |
C23—C2—C21—C22 | 64.69 (17) | C43—C4—C41—C42 | −46.88 (16) |
O2—C2—C23—C24 | −59.26 (16) | O4—C4—C43—C44 | −179.22 (14) |
C21—C2—C23—C24 | 56.11 (17) | C45—C4—C43—C44 | 66.29 (18) |
C25—C2—C23—C24 | −177.89 (13) | C41—C4—C43—C44 | −58.64 (18) |
O2—C2—C25—C26 | 58.77 (16) | O4—C4—C45—C46 | 62.17 (17) |
C21—C2—C25—C26 | −57.57 (17) | C41—C4—C45—C46 | −56.55 (18) |
C23—C2—C25—C26 | 176.67 (13) | C43—C4—C45—C46 | 177.75 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O4 | 0.84 (2) | 1.98 (2) | 2.7977 (16) | 167.7 (18) |
O2—H2···O1 | 0.86 (2) | 1.93 (2) | 2.7686 (14) | 165.8 (17) |
O3—H3···O2 | 0.87 (2) | 1.92 (2) | 2.7759 (15) | 169.4 (18) |
O4—H4···O3 | 0.81 (2) | 2.01 (2) | 2.7888 (15) | 160.5 (18) |