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
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.002 Å
- R factor = 0.044
- wR factor = 0.117
- Data-to-parameter ratio = 19.2
checkCIF/PLATON results
No syntax errors found
Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.693 0.975 Tmin(prime) and Tmax expected: 0.963 1.000 RR(prime) = 0.738 Please check that your absorption correction is appropriate. PLAT049_ALERT_1_B Calculated Density less than 1.0 gcm-3 ......... 0.99 PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.71
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
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) |