The title compound, C
26H
30O
7, crystallizes with three independent molecules in the asymmetric unit. The crystal structure is stabilized by intra- and intermolecular C—H
O hydrogen-bonding interactions.
Supporting information
CCDC reference: 630222
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- R factor = 0.045
- wR factor = 0.112
- Data-to-parameter ratio = 7.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for O7 - C26 .. 11.78 su
PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for O7
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.29
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.89 Ratio
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.79 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.52 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for O7 - C23 .. 5.67 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C25
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C26
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C27
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C62
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 25.01
From the CIF: _reflns_number_total 6625
Count of symmetry unique reflns 6628
Completeness (_total/calc) 99.95%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C30 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C31 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C32 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C35 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C39 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C40 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C41 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C43 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C56 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C57 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C58 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C61 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C65 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C66 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C67 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C69 = . S
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
12 ALERT level C = Check and explain
27 ALERT level G = General alerts; check
27 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
10 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.
Crystal data top
C26H30O7 | F(000) = 2904 |
Mr = 454.50 | Dx = 1.326 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2806 reflections |
a = 12.531 (2) Å | θ = 2.1–26.1° |
b = 23.041 (5) Å | µ = 0.10 mm−1 |
c = 23.649 (5) Å | T = 293 K |
V = 6828 (2) Å3 | Block, colourless |
Z = 12 | 0.30 × 0.25 × 0.20 mm |
Data collection top
Bruker SMART APEX area-detector diffractometer | 6625 independent reflections |
Radiation source: fine-focus sealed tube | 3328 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.098 |
φ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→13 |
Tmin = 0.972, Tmax = 0.981 | k = −27→26 |
34845 measured reflections | l = −28→23 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0501P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.84 | (Δ/σ)max < 0.001 |
6625 reflections | Δρmax = 0.20 e Å−3 |
909 parameters | Δρmin = −0.21 e Å−3 |
3402 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00153 (17) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.0005 (3) | 0.19056 (16) | 0.96013 (14) | 0.0771 (10) | |
O2 | −0.0878 (3) | 0.2288 (2) | 0.88883 (17) | 0.1064 (14) | |
O3 | 0.3613 (3) | 0.01825 (17) | 0.98026 (17) | 0.0873 (12) | |
O4 | 0.6046 (3) | 0.12341 (17) | 0.99122 (15) | 0.0886 (11) | |
O5 | 0.7003 (3) | 0.05236 (19) | 0.90189 (19) | 0.0978 (12) | |
O6 | 0.6939 (4) | −0.0168 (2) | 0.9663 (3) | 0.160 (2) | |
O7 | 0.7697 (4) | 0.1650 (3) | 0.7502 (3) | 0.159 (2) | |
O8 | 0.4192 (3) | 0.31591 (15) | 0.44019 (13) | 0.0654 (9) | |
O9 | 0.2742 (4) | 0.3495 (3) | 0.40004 (19) | 0.176 (3) | |
O10 | 0.6543 (2) | 0.39193 (15) | 0.65123 (13) | 0.0671 (9) | |
O11 | 0.5451 (2) | 0.26971 (14) | 0.75424 (12) | 0.0608 (8) | |
O12 | 0.5205 (2) | 0.36795 (15) | 0.83072 (12) | 0.0672 (9) | |
O13 | 0.6954 (3) | 0.36627 (16) | 0.83349 (14) | 0.0752 (10) | |
O14 | 0.1894 (3) | 0.4059 (2) | 0.88228 (17) | 0.1028 (14) | |
O15 | 1.0580 (2) | 0.32458 (13) | 0.67204 (13) | 0.0571 (8) | |
O16 | 1.0940 (3) | 0.24572 (15) | 0.72103 (16) | 0.0814 (11) | |
O17 | 0.7828 (3) | 0.54047 (14) | 0.65897 (13) | 0.0632 (9) | |
O18 | 0.8853 (2) | 0.61457 (13) | 0.79796 (12) | 0.0565 (8) | |
O19 | 0.6579 (3) | 0.63751 (13) | 0.81367 (14) | 0.0621 (9) | |
O20 | 0.6659 (3) | 0.68626 (14) | 0.73355 (14) | 0.0714 (10) | |
O21 | 0.5427 (4) | 0.55180 (18) | 0.97283 (18) | 0.0990 (13) | |
C1 | −0.0031 (5) | 0.2098 (2) | 0.9062 (2) | 0.0729 (15) | |
C2 | 0.0935 (5) | 0.2128 (2) | 0.8730 (2) | 0.0715 (14) | |
H2 | 0.0853 | 0.2220 | 0.8350 | 0.086* | |
C3 | 0.1915 (4) | 0.2039 (2) | 0.8905 (2) | 0.0657 (14) | |
H3 | 0.2445 | 0.2136 | 0.8647 | 0.079* | |
C4 | 0.2311 (4) | 0.1804 (2) | 0.94636 (19) | 0.0619 (12) | |
C5 | 0.3469 (4) | 0.1600 (2) | 0.93362 (19) | 0.0596 (12) | |
H5 | 0.3398 | 0.1357 | 0.8998 | 0.072* | |
C6 | 0.4041 (4) | 0.1199 (2) | 0.9777 (2) | 0.0630 (13) | |
C7 | 0.3316 (5) | 0.0675 (3) | 0.9849 (2) | 0.0748 (15) | |
C8 | 0.2168 (4) | 0.0818 (2) | 0.9994 (2) | 0.0784 (15) | |
H8A | 0.2142 | 0.0977 | 1.0373 | 0.094* | |
H8B | 0.1754 | 0.0463 | 0.9992 | 0.094* | |
C9 | 0.1645 (4) | 0.1257 (2) | 0.9582 (2) | 0.0617 (13) | |
H9 | 0.1612 | 0.1053 | 0.9219 | 0.074* | |
C10 | 0.0456 (4) | 0.1339 (3) | 0.9760 (2) | 0.0720 (15) | |
C11 | 0.4277 (4) | 0.2064 (2) | 0.9166 (2) | 0.0692 (14) | |
H11A | 0.3914 | 0.2374 | 0.8966 | 0.083* | |
H11B | 0.4599 | 0.2228 | 0.9503 | 0.083* | |
C12 | 0.5144 (4) | 0.1809 (2) | 0.8790 (2) | 0.0712 (14) | |
H12A | 0.5786 | 0.2041 | 0.8829 | 0.085* | |
H12B | 0.4915 | 0.1832 | 0.8399 | 0.085* | |
C13 | 0.5414 (4) | 0.1168 (2) | 0.8932 (2) | 0.0656 (13) | |
C14 | 0.5159 (4) | 0.1055 (2) | 0.9547 (2) | 0.0655 (13) | |
C15 | 0.5847 (5) | 0.0633 (3) | 0.9837 (3) | 0.0897 (17) | |
H15 | 0.5530 | 0.0427 | 1.0159 | 0.108* | |
C16 | 0.6643 (5) | 0.0309 (3) | 0.9503 (3) | 0.1013 (19) | |
C17 | 0.6642 (4) | 0.1102 (3) | 0.8842 (2) | 0.0799 (15) | |
H17 | 0.7004 | 0.1391 | 0.9078 | 0.096* | |
C18 | 0.2245 (5) | 0.2295 (2) | 0.9918 (2) | 0.0814 (16) | |
H18A | 0.1562 | 0.2481 | 0.9895 | 0.122* | |
H18B | 0.2798 | 0.2575 | 0.9849 | 0.122* | |
H18C | 0.2336 | 0.2130 | 1.0287 | 0.122* | |
C19 | 0.4154 (5) | 0.1472 (3) | 1.0374 (2) | 0.0943 (18) | |
H19A | 0.3460 | 0.1513 | 1.0542 | 0.141* | |
H19B | 0.4483 | 0.1847 | 1.0342 | 0.141* | |
H19C | 0.4587 | 0.1226 | 1.0607 | 0.141* | |
C20 | −0.0228 (4) | 0.0873 (3) | 0.9470 (2) | 0.0894 (18) | |
H20A | −0.0966 | 0.0935 | 0.9561 | 0.134* | |
H20B | −0.0012 | 0.0496 | 0.9598 | 0.134* | |
H20C | −0.0134 | 0.0898 | 0.9067 | 0.134* | |
C21 | 0.0251 (5) | 0.1334 (3) | 1.0391 (2) | 0.099 (2) | |
H21A | 0.0707 | 0.1612 | 1.0573 | 0.148* | |
H21B | 0.0397 | 0.0954 | 1.0539 | 0.148* | |
H21C | −0.0481 | 0.1432 | 1.0463 | 0.148* | |
C22 | 0.4837 (4) | 0.0731 (2) | 0.8551 (2) | 0.0780 (15) | |
H22A | 0.5160 | 0.0355 | 0.8592 | 0.117* | |
H22B | 0.4890 | 0.0854 | 0.8164 | 0.117* | |
H22C | 0.4098 | 0.0709 | 0.8658 | 0.117* | |
C23 | 0.7465 (5) | 0.1681 (4) | 0.8054 (3) | 0.122 (2) | |
H23 | 0.7596 | 0.2005 | 0.8277 | 0.147* | |
C24 | 0.7013 (4) | 0.1179 (3) | 0.8251 (3) | 0.0934 (17) | |
C25 | 0.7005 (6) | 0.0824 (4) | 0.7772 (4) | 0.130 (2) | |
H25 | 0.6739 | 0.0447 | 0.7776 | 0.156* | |
C26 | 0.7382 (5) | 0.1052 (4) | 0.7342 (3) | 0.126 (2) | |
H26 | 0.7453 | 0.0881 | 0.6988 | 0.151* | |
C27 | 0.3194 (5) | 0.3381 (3) | 0.4438 (2) | 0.0799 (16) | |
C28 | 0.2658 (4) | 0.3408 (2) | 0.4965 (2) | 0.0644 (13) | |
H28 | 0.1966 | 0.3553 | 0.4961 | 0.077* | |
C29 | 0.3040 (4) | 0.3248 (2) | 0.5460 (2) | 0.0604 (13) | |
H29 | 0.2555 | 0.3263 | 0.5757 | 0.073* | |
C30 | 0.4157 (3) | 0.30432 (19) | 0.56203 (17) | 0.0431 (10) | |
C31 | 0.4236 (3) | 0.31523 (18) | 0.62623 (16) | 0.0421 (10) | |
H31 | 0.4062 | 0.3565 | 0.6304 | 0.051* | |
C32 | 0.5348 (3) | 0.30931 (19) | 0.65448 (18) | 0.0470 (11) | |
C33 | 0.6032 (3) | 0.3545 (2) | 0.62557 (19) | 0.0519 (11) | |
C34 | 0.6060 (3) | 0.3510 (2) | 0.56217 (18) | 0.0619 (13) | |
H34A | 0.6468 | 0.3170 | 0.5514 | 0.074* | |
H34B | 0.6435 | 0.3848 | 0.5478 | 0.074* | |
C35 | 0.4957 (3) | 0.3477 (2) | 0.53325 (17) | 0.0504 (11) | |
H35 | 0.4641 | 0.3861 | 0.5397 | 0.060* | |
C36 | 0.5097 (3) | 0.3442 (2) | 0.46792 (18) | 0.0521 (12) | |
C37 | 0.3438 (3) | 0.28453 (19) | 0.66513 (17) | 0.0499 (11) | |
H37A | 0.2775 | 0.2775 | 0.6451 | 0.060* | |
H37B | 0.3725 | 0.2475 | 0.6773 | 0.060* | |
C38 | 0.3237 (3) | 0.3232 (2) | 0.71606 (18) | 0.0528 (12) | |
H38A | 0.2918 | 0.3000 | 0.7458 | 0.063* | |
H38B | 0.2725 | 0.3529 | 0.7055 | 0.063* | |
C39 | 0.4249 (3) | 0.35334 (19) | 0.73993 (16) | 0.0427 (10) | |
C40 | 0.5219 (3) | 0.3196 (2) | 0.71899 (17) | 0.0461 (11) | |
C41 | 0.6156 (4) | 0.3181 (2) | 0.75609 (19) | 0.0534 (12) | |
H41 | 0.6848 | 0.3130 | 0.7374 | 0.064* | |
C42 | 0.6160 (4) | 0.3521 (2) | 0.8096 (2) | 0.0568 (12) | |
C43 | 0.4216 (3) | 0.3474 (2) | 0.80498 (18) | 0.0601 (12) | |
H43 | 0.4120 | 0.3063 | 0.8146 | 0.072* | |
C44 | 0.4265 (4) | 0.23985 (19) | 0.54478 (19) | 0.0621 (13) | |
H44A | 0.5006 | 0.2294 | 0.5437 | 0.093* | |
H44B | 0.3954 | 0.2342 | 0.5081 | 0.093* | |
H44C | 0.3901 | 0.2160 | 0.5719 | 0.093* | |
C45 | 0.5888 (4) | 0.2496 (2) | 0.6462 (2) | 0.0690 (14) | |
H45A | 0.6134 | 0.2462 | 0.6079 | 0.104* | |
H45B | 0.5383 | 0.2193 | 0.6540 | 0.104* | |
H45C | 0.6483 | 0.2462 | 0.6715 | 0.104* | |
C46 | 0.5184 (4) | 0.4047 (2) | 0.44315 (19) | 0.0679 (14) | |
H46A | 0.5299 | 0.4021 | 0.4031 | 0.102* | |
H46B | 0.5773 | 0.4247 | 0.4603 | 0.102* | |
H46C | 0.4536 | 0.4257 | 0.4503 | 0.102* | |
C47 | 0.6014 (4) | 0.3068 (2) | 0.4475 (2) | 0.0720 (15) | |
H47A | 0.5968 | 0.2691 | 0.4646 | 0.108* | |
H47B | 0.6679 | 0.3246 | 0.4577 | 0.108* | |
H47C | 0.5977 | 0.3029 | 0.4071 | 0.108* | |
C48 | 0.4320 (3) | 0.41737 (19) | 0.72268 (18) | 0.0547 (12) | |
H48A | 0.4918 | 0.4351 | 0.7412 | 0.082* | |
H48B | 0.3676 | 0.4370 | 0.7336 | 0.082* | |
H48C | 0.4409 | 0.4201 | 0.6825 | 0.082* | |
C49 | 0.2446 (4) | 0.3627 (3) | 0.8563 (2) | 0.0817 (16) | |
H49 | 0.2214 | 0.3244 | 0.8539 | 0.098* | |
C50 | 0.3366 (4) | 0.3824 (3) | 0.8347 (2) | 0.0649 (13) | |
C51 | 0.3383 (5) | 0.4419 (3) | 0.8501 (2) | 0.0889 (17) | |
H51 | 0.3923 | 0.4684 | 0.8423 | 0.107* | |
C52 | 0.2492 (5) | 0.4526 (3) | 0.8775 (3) | 0.099 (2) | |
H52 | 0.2305 | 0.4888 | 0.8917 | 0.119* | |
C53 | 1.0377 (4) | 0.2884 (2) | 0.7158 (2) | 0.0599 (13) | |
C54 | 0.9604 (3) | 0.3050 (2) | 0.7579 (2) | 0.0580 (12) | |
H54 | 0.9267 | 0.2750 | 0.7773 | 0.070* | |
C55 | 0.9324 (3) | 0.3587 (2) | 0.7719 (2) | 0.0541 (12) | |
H55 | 0.8885 | 0.3628 | 0.8034 | 0.065* | |
C56 | 0.9650 (3) | 0.41435 (18) | 0.74172 (16) | 0.0422 (10) | |
C57 | 0.8975 (3) | 0.46329 (17) | 0.76889 (16) | 0.0419 (10) | |
H57 | 0.8238 | 0.4497 | 0.7649 | 0.050* | |
C58 | 0.8977 (3) | 0.52331 (19) | 0.73865 (18) | 0.0470 (11) | |
C59 | 0.8537 (4) | 0.5126 (2) | 0.67990 (18) | 0.0485 (11) | |
C60 | 0.9098 (4) | 0.4645 (2) | 0.64788 (18) | 0.0573 (12) | |
H60A | 0.9801 | 0.4781 | 0.6370 | 0.069* | |
H60B | 0.8703 | 0.4568 | 0.6134 | 0.069* | |
C61 | 0.9224 (3) | 0.40707 (18) | 0.68051 (16) | 0.0473 (11) | |
H61 | 0.8492 | 0.3930 | 0.6854 | 0.057* | |
C62 | 0.9773 (4) | 0.3598 (2) | 0.6432 (2) | 0.0663 (14) | |
C63 | 0.9098 (3) | 0.47394 (19) | 0.83268 (17) | 0.0512 (11) | |
H63A | 0.9680 | 0.5008 | 0.8395 | 0.061* | |
H63B | 0.9260 | 0.4377 | 0.8517 | 0.061* | |
C64 | 0.8051 (3) | 0.49936 (18) | 0.85607 (17) | 0.0487 (11) | |
H64A | 0.8206 | 0.5198 | 0.8910 | 0.058* | |
H64B | 0.7572 | 0.4676 | 0.8651 | 0.058* | |
C65 | 0.7467 (3) | 0.54172 (19) | 0.81513 (17) | 0.0451 (11) | |
C66 | 0.8290 (3) | 0.56534 (18) | 0.77308 (17) | 0.0428 (10) | |
C67 | 0.8109 (4) | 0.62455 (19) | 0.7527 (2) | 0.0546 (12) | |
H67 | 0.8421 | 0.6340 | 0.7158 | 0.066* | |
C68 | 0.7079 (4) | 0.6526 (2) | 0.7658 (2) | 0.0562 (12) | |
C69 | 0.7048 (4) | 0.59314 (19) | 0.85058 (19) | 0.0530 (11) | |
H69 | 0.7649 | 0.6104 | 0.8710 | 0.064* | |
C70 | 1.0864 (3) | 0.4243 (2) | 0.74710 (18) | 0.0555 (12) | |
H70A | 1.1002 | 0.4504 | 0.7778 | 0.083* | |
H70B | 1.1132 | 0.4406 | 0.7126 | 0.083* | |
H70C | 1.1212 | 0.3879 | 0.7542 | 0.083* | |
C71 | 1.0095 (3) | 0.5512 (2) | 0.7308 (2) | 0.0661 (14) | |
H71A | 1.0502 | 0.5287 | 0.7044 | 0.099* | |
H71B | 1.0459 | 0.5523 | 0.7665 | 0.099* | |
H71C | 1.0014 | 0.5900 | 0.7166 | 0.099* | |
C72 | 0.8912 (4) | 0.3167 (3) | 0.6220 (2) | 0.106 (2) | |
H72A | 0.9240 | 0.2877 | 0.5987 | 0.158* | |
H72B | 0.8386 | 0.3373 | 0.6004 | 0.158* | |
H72C | 0.8575 | 0.2985 | 0.6538 | 0.158* | |
C73 | 1.0421 (5) | 0.3831 (3) | 0.5953 (2) | 0.117 (2) | |
H73A | 1.0943 | 0.4098 | 0.6097 | 0.176* | |
H73B | 0.9961 | 0.4028 | 0.5691 | 0.176* | |
H73C | 1.0775 | 0.3517 | 0.5764 | 0.176* | |
C74 | 0.6530 (3) | 0.51264 (19) | 0.78365 (18) | 0.0497 (12) | |
H74A | 0.6107 | 0.5419 | 0.7653 | 0.075* | |
H74B | 0.6095 | 0.4918 | 0.8102 | 0.075* | |
H74C | 0.6804 | 0.4862 | 0.7558 | 0.075* | |
C75 | 0.6365 (5) | 0.5636 (2) | 0.9463 (2) | 0.0790 (15) | |
H75 | 0.7033 | 0.5615 | 0.9634 | 0.095* | |
C76 | 0.6196 (4) | 0.5787 (2) | 0.8920 (2) | 0.0615 (13) | |
C77 | 0.5086 (5) | 0.5787 (2) | 0.8843 (2) | 0.0813 (16) | |
H77 | 0.4722 | 0.5885 | 0.8514 | 0.098* | |
C78 | 0.4639 (5) | 0.5616 (3) | 0.9342 (3) | 0.0936 (18) | |
H78 | 0.3911 | 0.5572 | 0.9408 | 0.112* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.100 (3) | 0.076 (3) | 0.055 (2) | 0.023 (2) | 0.011 (2) | −0.0080 (19) |
O2 | 0.092 (3) | 0.132 (4) | 0.095 (3) | 0.037 (3) | 0.000 (3) | 0.011 (3) |
O3 | 0.089 (3) | 0.057 (3) | 0.116 (3) | 0.001 (2) | −0.004 (2) | 0.022 (2) |
O4 | 0.095 (2) | 0.092 (3) | 0.079 (2) | −0.017 (2) | −0.042 (2) | 0.025 (2) |
O5 | 0.075 (2) | 0.092 (3) | 0.126 (3) | 0.004 (2) | −0.015 (2) | 0.031 (3) |
O6 | 0.124 (4) | 0.114 (4) | 0.243 (6) | 0.031 (3) | 0.018 (4) | 0.084 (4) |
O7 | 0.109 (3) | 0.222 (5) | 0.148 (4) | 0.025 (4) | 0.010 (3) | 0.063 (5) |
O8 | 0.062 (2) | 0.079 (2) | 0.0552 (19) | −0.0176 (19) | 0.0025 (17) | −0.0162 (18) |
O9 | 0.091 (3) | 0.367 (8) | 0.071 (3) | 0.005 (4) | −0.010 (3) | 0.036 (4) |
O10 | 0.060 (2) | 0.082 (3) | 0.058 (2) | −0.0236 (19) | −0.0018 (18) | −0.0019 (19) |
O11 | 0.0573 (19) | 0.058 (2) | 0.067 (2) | 0.0022 (16) | −0.0087 (16) | 0.0162 (17) |
O12 | 0.0510 (19) | 0.105 (3) | 0.0461 (18) | 0.0046 (19) | −0.0066 (16) | 0.0026 (18) |
O13 | 0.0494 (19) | 0.103 (3) | 0.073 (2) | −0.002 (2) | −0.0116 (19) | −0.003 (2) |
O14 | 0.078 (3) | 0.155 (4) | 0.075 (3) | 0.024 (3) | 0.027 (2) | 0.012 (3) |
O15 | 0.0478 (18) | 0.062 (2) | 0.061 (2) | 0.0190 (16) | −0.0004 (16) | −0.0035 (17) |
O16 | 0.077 (2) | 0.054 (2) | 0.113 (3) | 0.024 (2) | 0.016 (2) | 0.004 (2) |
O17 | 0.069 (2) | 0.062 (2) | 0.059 (2) | 0.0175 (19) | −0.0102 (18) | 0.0066 (17) |
O18 | 0.0636 (18) | 0.0418 (18) | 0.064 (2) | −0.0074 (16) | −0.0082 (17) | −0.0061 (15) |
O19 | 0.081 (2) | 0.0405 (19) | 0.065 (2) | 0.0153 (17) | 0.0073 (19) | −0.0030 (16) |
O20 | 0.099 (3) | 0.052 (2) | 0.063 (2) | 0.022 (2) | −0.011 (2) | 0.0011 (18) |
O21 | 0.110 (3) | 0.095 (3) | 0.093 (3) | 0.004 (3) | 0.034 (3) | −0.005 (2) |
C1 | 0.090 (4) | 0.061 (3) | 0.067 (3) | 0.016 (3) | −0.001 (3) | −0.012 (3) |
C2 | 0.089 (4) | 0.071 (3) | 0.055 (3) | 0.022 (3) | 0.001 (3) | 0.001 (3) |
C3 | 0.080 (3) | 0.061 (3) | 0.056 (3) | 0.011 (3) | 0.002 (3) | 0.009 (2) |
C4 | 0.086 (3) | 0.050 (3) | 0.049 (3) | 0.001 (3) | −0.002 (3) | 0.001 (2) |
C5 | 0.081 (3) | 0.049 (3) | 0.048 (3) | −0.002 (3) | −0.010 (2) | 0.007 (2) |
C6 | 0.079 (3) | 0.057 (3) | 0.053 (3) | −0.003 (3) | −0.012 (2) | 0.010 (2) |
C7 | 0.090 (4) | 0.063 (3) | 0.071 (3) | 0.004 (3) | −0.008 (3) | 0.021 (3) |
C8 | 0.088 (3) | 0.068 (3) | 0.080 (3) | 0.003 (3) | 0.005 (3) | 0.017 (3) |
C9 | 0.081 (3) | 0.056 (3) | 0.048 (3) | 0.004 (3) | 0.001 (3) | −0.002 (2) |
C10 | 0.090 (3) | 0.078 (4) | 0.048 (3) | 0.011 (3) | 0.008 (3) | 0.004 (3) |
C11 | 0.083 (3) | 0.056 (3) | 0.068 (3) | −0.005 (3) | −0.020 (3) | 0.008 (2) |
C12 | 0.075 (3) | 0.068 (3) | 0.071 (3) | −0.007 (3) | −0.014 (3) | 0.018 (3) |
C13 | 0.071 (3) | 0.059 (3) | 0.067 (3) | −0.003 (3) | −0.021 (3) | 0.008 (2) |
C14 | 0.073 (3) | 0.057 (3) | 0.067 (3) | −0.014 (3) | −0.028 (3) | 0.019 (2) |
C15 | 0.080 (3) | 0.085 (4) | 0.105 (4) | 0.004 (3) | −0.018 (3) | 0.044 (3) |
C16 | 0.086 (4) | 0.087 (4) | 0.130 (5) | 0.011 (4) | −0.019 (4) | 0.041 (4) |
C17 | 0.067 (3) | 0.083 (3) | 0.090 (3) | −0.004 (3) | −0.017 (3) | 0.026 (3) |
C18 | 0.111 (4) | 0.066 (4) | 0.067 (3) | 0.004 (3) | −0.005 (3) | −0.017 (3) |
C19 | 0.131 (5) | 0.094 (4) | 0.057 (3) | 0.002 (4) | −0.029 (3) | 0.003 (3) |
C20 | 0.090 (4) | 0.084 (4) | 0.093 (4) | 0.000 (4) | 0.004 (4) | −0.009 (4) |
C21 | 0.124 (5) | 0.119 (5) | 0.053 (3) | 0.015 (4) | 0.025 (3) | 0.011 (3) |
C22 | 0.065 (3) | 0.082 (4) | 0.087 (4) | −0.006 (3) | −0.012 (3) | −0.020 (3) |
C23 | 0.107 (4) | 0.147 (5) | 0.113 (4) | 0.004 (4) | 0.003 (4) | 0.031 (4) |
C24 | 0.058 (3) | 0.122 (5) | 0.100 (4) | −0.011 (3) | −0.013 (3) | 0.011 (4) |
C25 | 0.095 (4) | 0.164 (6) | 0.132 (5) | −0.032 (4) | 0.003 (4) | 0.000 (5) |
C26 | 0.077 (4) | 0.204 (7) | 0.098 (5) | −0.021 (5) | 0.000 (4) | −0.008 (5) |
C27 | 0.070 (3) | 0.116 (4) | 0.054 (3) | −0.015 (3) | −0.012 (3) | 0.004 (3) |
C28 | 0.051 (3) | 0.090 (4) | 0.053 (3) | 0.005 (3) | 0.000 (3) | 0.003 (3) |
C29 | 0.049 (3) | 0.080 (3) | 0.053 (3) | −0.003 (3) | 0.003 (2) | −0.003 (3) |
C30 | 0.039 (2) | 0.049 (3) | 0.042 (2) | −0.008 (2) | 0.001 (2) | −0.002 (2) |
C31 | 0.040 (2) | 0.041 (2) | 0.045 (2) | 0.001 (2) | 0.003 (2) | 0.002 (2) |
C32 | 0.038 (2) | 0.050 (3) | 0.053 (3) | −0.006 (2) | 0.000 (2) | 0.002 (2) |
C33 | 0.039 (2) | 0.067 (3) | 0.050 (3) | −0.003 (2) | 0.000 (2) | 0.000 (2) |
C34 | 0.048 (3) | 0.083 (3) | 0.055 (3) | −0.016 (3) | 0.005 (2) | 0.002 (3) |
C35 | 0.050 (2) | 0.054 (3) | 0.047 (2) | −0.010 (2) | 0.004 (2) | −0.002 (2) |
C36 | 0.050 (3) | 0.063 (3) | 0.043 (2) | −0.009 (2) | 0.002 (2) | −0.007 (2) |
C37 | 0.049 (2) | 0.054 (3) | 0.047 (3) | −0.011 (2) | 0.002 (2) | 0.001 (2) |
C38 | 0.041 (2) | 0.065 (3) | 0.052 (3) | −0.004 (2) | 0.002 (2) | 0.005 (2) |
C39 | 0.034 (2) | 0.053 (3) | 0.042 (2) | 0.002 (2) | 0.0011 (19) | 0.007 (2) |
C40 | 0.039 (2) | 0.055 (3) | 0.044 (2) | −0.002 (2) | −0.004 (2) | 0.013 (2) |
C41 | 0.045 (2) | 0.061 (3) | 0.054 (3) | −0.001 (2) | 0.000 (2) | 0.001 (2) |
C42 | 0.050 (3) | 0.072 (3) | 0.049 (3) | 0.001 (3) | −0.002 (3) | 0.016 (2) |
C43 | 0.044 (2) | 0.090 (3) | 0.046 (3) | −0.007 (2) | −0.003 (2) | 0.011 (2) |
C44 | 0.073 (3) | 0.050 (3) | 0.063 (3) | −0.007 (3) | 0.003 (3) | −0.007 (2) |
C45 | 0.064 (3) | 0.065 (3) | 0.078 (3) | 0.024 (3) | −0.009 (3) | −0.007 (3) |
C46 | 0.078 (3) | 0.073 (4) | 0.053 (3) | −0.014 (3) | 0.002 (3) | 0.007 (3) |
C47 | 0.065 (3) | 0.087 (4) | 0.064 (3) | 0.008 (3) | 0.024 (3) | −0.020 (3) |
C48 | 0.060 (3) | 0.052 (3) | 0.052 (3) | −0.005 (2) | −0.001 (2) | −0.002 (2) |
C49 | 0.071 (3) | 0.102 (4) | 0.073 (3) | 0.008 (3) | 0.012 (3) | 0.019 (3) |
C50 | 0.046 (3) | 0.103 (4) | 0.045 (3) | 0.000 (3) | 0.003 (2) | 0.008 (3) |
C51 | 0.075 (3) | 0.119 (4) | 0.072 (3) | −0.009 (3) | 0.015 (3) | −0.025 (3) |
C52 | 0.091 (4) | 0.135 (5) | 0.070 (4) | 0.014 (4) | 0.007 (4) | −0.033 (4) |
C53 | 0.052 (3) | 0.052 (3) | 0.075 (3) | 0.003 (3) | 0.000 (3) | −0.009 (3) |
C54 | 0.055 (3) | 0.050 (3) | 0.070 (3) | 0.008 (2) | 0.007 (3) | −0.001 (2) |
C55 | 0.049 (2) | 0.053 (3) | 0.060 (3) | 0.011 (2) | 0.008 (2) | 0.000 (2) |
C56 | 0.045 (2) | 0.045 (2) | 0.037 (2) | 0.008 (2) | 0.001 (2) | 0.000 (2) |
C57 | 0.042 (2) | 0.047 (2) | 0.037 (2) | 0.003 (2) | −0.0050 (19) | −0.0012 (19) |
C58 | 0.049 (2) | 0.047 (3) | 0.046 (2) | 0.002 (2) | −0.005 (2) | 0.000 (2) |
C59 | 0.053 (3) | 0.047 (3) | 0.045 (3) | 0.003 (2) | −0.002 (2) | 0.005 (2) |
C60 | 0.062 (3) | 0.065 (3) | 0.045 (3) | 0.015 (3) | 0.001 (2) | 0.003 (2) |
C61 | 0.048 (2) | 0.049 (3) | 0.046 (2) | 0.011 (2) | −0.002 (2) | −0.005 (2) |
C62 | 0.063 (3) | 0.082 (3) | 0.054 (3) | 0.033 (3) | −0.004 (3) | −0.017 (3) |
C63 | 0.061 (3) | 0.053 (3) | 0.040 (2) | 0.003 (2) | −0.004 (2) | 0.002 (2) |
C64 | 0.067 (3) | 0.041 (3) | 0.039 (2) | 0.008 (2) | −0.001 (2) | −0.007 (2) |
C65 | 0.053 (2) | 0.039 (2) | 0.043 (2) | 0.005 (2) | −0.003 (2) | −0.004 (2) |
C66 | 0.050 (2) | 0.036 (2) | 0.042 (2) | −0.004 (2) | −0.010 (2) | −0.002 (2) |
C67 | 0.068 (3) | 0.040 (3) | 0.055 (3) | −0.001 (2) | 0.001 (2) | 0.001 (2) |
C68 | 0.079 (3) | 0.040 (3) | 0.050 (3) | 0.006 (3) | −0.008 (3) | −0.012 (2) |
C69 | 0.069 (3) | 0.038 (3) | 0.051 (3) | 0.006 (2) | −0.003 (2) | −0.011 (2) |
C70 | 0.040 (3) | 0.066 (3) | 0.060 (3) | 0.010 (2) | −0.003 (2) | −0.002 (2) |
C71 | 0.054 (3) | 0.059 (3) | 0.086 (4) | −0.006 (3) | 0.008 (3) | 0.000 (3) |
C72 | 0.088 (4) | 0.112 (5) | 0.117 (5) | 0.043 (4) | −0.043 (4) | −0.070 (4) |
C73 | 0.139 (5) | 0.149 (6) | 0.063 (4) | 0.092 (5) | 0.040 (4) | 0.029 (4) |
C74 | 0.048 (3) | 0.047 (3) | 0.054 (3) | 0.005 (2) | 0.001 (2) | −0.011 (2) |
C75 | 0.083 (4) | 0.080 (4) | 0.074 (4) | 0.004 (3) | 0.026 (3) | −0.009 (3) |
C76 | 0.075 (3) | 0.053 (3) | 0.056 (3) | 0.005 (3) | 0.011 (3) | −0.009 (2) |
C77 | 0.082 (4) | 0.080 (4) | 0.082 (4) | 0.013 (3) | 0.013 (3) | −0.012 (3) |
C78 | 0.083 (4) | 0.095 (4) | 0.103 (4) | 0.005 (4) | 0.033 (4) | −0.028 (4) |
Geometric parameters (Å, º) top
O1—C1 | 1.352 (6) | C32—C45 | 1.546 (6) |
O1—C10 | 1.471 (6) | C32—C40 | 1.552 (6) |
O2—C1 | 1.219 (6) | C33—C34 | 1.502 (6) |
O3—C7 | 1.198 (6) | C34—C35 | 1.544 (6) |
O4—C15 | 1.420 (7) | C34—H34A | 0.9700 |
O4—C14 | 1.466 (5) | C34—H34B | 0.9700 |
O5—C16 | 1.325 (7) | C35—C36 | 1.557 (6) |
O5—C17 | 1.468 (6) | C35—H35 | 0.9800 |
O6—C16 | 1.222 (7) | C36—C47 | 1.515 (6) |
O7—C23 | 1.339 (8) | C36—C46 | 1.517 (6) |
O7—C26 | 1.482 (9) | C37—C38 | 1.520 (6) |
O8—C27 | 1.353 (6) | C37—H37A | 0.9700 |
O8—C36 | 1.463 (5) | C37—H37B | 0.9700 |
O9—C27 | 1.210 (6) | C38—C39 | 1.551 (5) |
O10—C33 | 1.233 (5) | C38—H38A | 0.9700 |
O11—C41 | 1.423 (5) | C38—H38B | 0.9700 |
O11—C40 | 1.449 (5) | C39—C40 | 1.526 (5) |
O12—C42 | 1.347 (5) | C39—C48 | 1.533 (6) |
O12—C43 | 1.460 (5) | C39—C43 | 1.545 (5) |
O13—C42 | 1.190 (5) | C40—C41 | 1.466 (6) |
O14—C52 | 1.317 (7) | C41—C42 | 1.488 (6) |
O14—C49 | 1.358 (6) | C41—H41 | 0.9800 |
O15—C53 | 1.353 (6) | C43—C50 | 1.510 (7) |
O15—C62 | 1.465 (5) | C43—H43 | 0.9800 |
O16—C53 | 1.216 (5) | C44—H44A | 0.9600 |
O17—C59 | 1.203 (5) | C44—H44B | 0.9600 |
O18—C67 | 1.438 (5) | C44—H44C | 0.9600 |
O18—C66 | 1.460 (5) | C45—H45A | 0.9600 |
O19—C68 | 1.339 (5) | C45—H45B | 0.9600 |
O19—C69 | 1.467 (5) | C45—H45C | 0.9600 |
O20—C68 | 1.209 (5) | C46—H46A | 0.9600 |
O21—C75 | 1.360 (6) | C46—H46B | 0.9600 |
O21—C78 | 1.364 (7) | C46—H46C | 0.9600 |
C1—C2 | 1.444 (7) | C47—H47A | 0.9600 |
C2—C3 | 1.312 (6) | C47—H47B | 0.9600 |
C2—H2 | 0.9300 | C47—H47C | 0.9600 |
C3—C4 | 1.512 (6) | C48—H48A | 0.9600 |
C3—H3 | 0.9300 | C48—H48B | 0.9600 |
C4—C9 | 1.538 (6) | C48—H48C | 0.9600 |
C4—C5 | 1.554 (7) | C49—C50 | 1.340 (6) |
C4—C18 | 1.562 (6) | C49—H49 | 0.9300 |
C5—C11 | 1.527 (6) | C50—C51 | 1.420 (7) |
C5—C6 | 1.566 (6) | C51—C52 | 1.314 (7) |
C5—H5 | 0.9800 | C51—H51 | 0.9300 |
C6—C7 | 1.521 (7) | C52—H52 | 0.9300 |
C6—C14 | 1.539 (7) | C53—C54 | 1.441 (6) |
C6—C19 | 1.554 (7) | C54—C55 | 1.329 (6) |
C7—C8 | 1.516 (7) | C54—H54 | 0.9300 |
C8—C9 | 1.548 (6) | C55—C56 | 1.523 (6) |
C8—H8A | 0.9700 | C55—H55 | 0.9300 |
C8—H8B | 0.9700 | C56—C70 | 1.543 (6) |
C9—C10 | 1.560 (7) | C56—C57 | 1.549 (5) |
C9—H9 | 0.9800 | C56—C61 | 1.552 (5) |
C10—C21 | 1.514 (6) | C57—C63 | 1.536 (5) |
C10—C20 | 1.537 (7) | C57—C58 | 1.557 (6) |
C11—C12 | 1.523 (6) | C57—H57 | 0.9800 |
C11—H11A | 0.9700 | C58—C59 | 1.515 (6) |
C11—H11B | 0.9700 | C58—C66 | 1.531 (6) |
C12—C13 | 1.551 (7) | C58—C71 | 1.552 (6) |
C12—H12A | 0.9700 | C59—C60 | 1.515 (6) |
C12—H12B | 0.9700 | C60—C61 | 1.539 (6) |
C13—C14 | 1.510 (7) | C60—H60A | 0.9700 |
C13—C22 | 1.534 (6) | C60—H60B | 0.9700 |
C13—C17 | 1.562 (7) | C61—C62 | 1.562 (6) |
C14—C15 | 1.471 (7) | C61—H61 | 0.9800 |
C15—C16 | 1.475 (9) | C62—C73 | 1.493 (7) |
C15—H15 | 0.9800 | C62—C72 | 1.549 (7) |
C17—C24 | 1.482 (8) | C63—C64 | 1.539 (6) |
C17—H17 | 0.9800 | C63—H63A | 0.9700 |
C18—H18A | 0.9600 | C63—H63B | 0.9700 |
C18—H18B | 0.9600 | C64—C65 | 1.557 (6) |
C18—H18C | 0.9600 | C64—H64A | 0.9700 |
C19—H19A | 0.9600 | C64—H64B | 0.9700 |
C19—H19B | 0.9600 | C65—C66 | 1.532 (6) |
C19—H19C | 0.9600 | C65—C69 | 1.544 (5) |
C20—H20A | 0.9600 | C65—C74 | 1.544 (6) |
C20—H20B | 0.9600 | C66—C67 | 1.465 (6) |
C20—H20C | 0.9600 | C67—C68 | 1.476 (6) |
C21—H21A | 0.9600 | C67—H67 | 0.9800 |
C21—H21B | 0.9600 | C69—C76 | 1.486 (6) |
C21—H21C | 0.9600 | C69—H69 | 0.9800 |
C22—H22A | 0.9600 | C70—H70A | 0.9600 |
C22—H22B | 0.9600 | C70—H70B | 0.9600 |
C22—H22C | 0.9600 | C70—H70C | 0.9600 |
C23—C24 | 1.369 (9) | C71—H71A | 0.9600 |
C23—H23 | 0.9300 | C71—H71B | 0.9600 |
C24—C25 | 1.398 (9) | C71—H71C | 0.9600 |
C25—C26 | 1.237 (9) | C72—H72A | 0.9600 |
C25—H25 | 0.9300 | C72—H72B | 0.9600 |
C26—H26 | 0.9300 | C72—H72C | 0.9600 |
C27—C28 | 1.418 (7) | C73—H73A | 0.9600 |
C28—C29 | 1.316 (6) | C73—H73B | 0.9600 |
C28—H28 | 0.9300 | C73—H73C | 0.9600 |
C29—C30 | 1.525 (6) | C74—H74A | 0.9600 |
C29—H29 | 0.9300 | C74—H74B | 0.9600 |
C30—C31 | 1.542 (5) | C74—H74C | 0.9600 |
C30—C44 | 1.546 (6) | C75—C76 | 1.347 (7) |
C30—C35 | 1.571 (6) | C75—H75 | 0.9300 |
C31—C37 | 1.532 (5) | C76—C77 | 1.404 (7) |
C31—C32 | 1.551 (5) | C77—C78 | 1.363 (7) |
C31—H31 | 0.9800 | C77—H77 | 0.9300 |
C32—C33 | 1.513 (6) | C78—H78 | 0.9300 |
| | | |
C1—O1—C10 | 123.0 (4) | H38A—C38—H38B | 107.6 |
C15—O4—C14 | 61.2 (3) | C40—C39—C48 | 111.0 (3) |
C16—O5—C17 | 118.7 (5) | C40—C39—C43 | 107.4 (3) |
C23—O7—C26 | 103.9 (7) | C48—C39—C43 | 110.6 (4) |
C27—O8—C36 | 121.3 (4) | C40—C39—C38 | 107.7 (3) |
C41—O11—C40 | 61.4 (3) | C48—C39—C38 | 112.4 (3) |
C42—O12—C43 | 120.7 (4) | C43—C39—C38 | 107.5 (3) |
C52—O14—C49 | 105.7 (5) | O11—C40—C41 | 58.4 (3) |
C53—O15—C62 | 124.6 (4) | O11—C40—C39 | 112.2 (3) |
C67—O18—C66 | 60.7 (3) | C41—C40—C39 | 117.1 (4) |
C68—O19—C69 | 119.8 (4) | O11—C40—C32 | 115.1 (4) |
C75—O21—C78 | 106.5 (5) | C41—C40—C32 | 120.1 (4) |
O2—C1—O1 | 117.7 (5) | C39—C40—C32 | 118.7 (3) |
O2—C1—C2 | 122.0 (5) | O11—C41—C40 | 60.2 (3) |
O1—C1—C2 | 120.0 (5) | O11—C41—C42 | 116.2 (4) |
C3—C2—C1 | 127.3 (5) | C40—C41—C42 | 120.0 (4) |
C3—C2—H2 | 116.3 | O11—C41—H41 | 116.2 |
C1—C2—H2 | 116.3 | C40—C41—H41 | 116.2 |
C2—C3—C4 | 129.7 (5) | C42—C41—H41 | 116.2 |
C2—C3—H3 | 115.2 | O13—C42—O12 | 119.4 (5) |
C4—C3—H3 | 115.2 | O13—C42—C41 | 123.5 (5) |
C3—C4—C9 | 106.0 (4) | O12—C42—C41 | 117.1 (4) |
C3—C4—C5 | 104.2 (4) | O12—C43—C50 | 103.4 (4) |
C9—C4—C5 | 107.1 (4) | O12—C43—C39 | 111.3 (3) |
C3—C4—C18 | 108.8 (4) | C50—C43—C39 | 115.8 (4) |
C9—C4—C18 | 116.1 (4) | O12—C43—H43 | 108.7 |
C5—C4—C18 | 113.7 (4) | C50—C43—H43 | 108.7 |
C11—C5—C4 | 117.3 (4) | C39—C43—H43 | 108.7 |
C11—C5—C6 | 106.5 (4) | C30—C44—H44A | 109.5 |
C4—C5—C6 | 118.5 (4) | C30—C44—H44B | 109.5 |
C11—C5—H5 | 104.3 | H44A—C44—H44B | 109.5 |
C4—C5—H5 | 104.3 | C30—C44—H44C | 109.5 |
C6—C5—H5 | 104.3 | H44A—C44—H44C | 109.5 |
C7—C6—C14 | 114.4 (4) | H44B—C44—H44C | 109.5 |
C7—C6—C19 | 105.9 (4) | C32—C45—H45A | 109.5 |
C14—C6—C19 | 109.0 (4) | C32—C45—H45B | 109.5 |
C7—C6—C5 | 105.7 (4) | H45A—C45—H45B | 109.5 |
C14—C6—C5 | 108.0 (4) | C32—C45—H45C | 109.5 |
C19—C6—C5 | 114.0 (4) | H45A—C45—H45C | 109.5 |
O3—C7—C8 | 121.5 (5) | H45B—C45—H45C | 109.5 |
O3—C7—C6 | 123.8 (5) | C36—C46—H46A | 109.5 |
C8—C7—C6 | 114.7 (5) | C36—C46—H46B | 109.5 |
C7—C8—C9 | 113.7 (4) | H46A—C46—H46B | 109.5 |
C7—C8—H8A | 108.8 | C36—C46—H46C | 109.5 |
C9—C8—H8A | 108.8 | H46A—C46—H46C | 109.5 |
C7—C8—H8B | 108.8 | H46B—C46—H46C | 109.5 |
C9—C8—H8B | 108.8 | C36—C47—H47A | 109.5 |
H8A—C8—H8B | 107.7 | C36—C47—H47B | 109.5 |
C4—C9—C8 | 114.8 (4) | H47A—C47—H47B | 109.5 |
C4—C9—C10 | 117.9 (4) | C36—C47—H47C | 109.5 |
C8—C9—C10 | 108.3 (4) | H47A—C47—H47C | 109.5 |
C4—C9—H9 | 104.8 | H47B—C47—H47C | 109.5 |
C8—C9—H9 | 104.8 | C39—C48—H48A | 109.5 |
C10—C9—H9 | 104.8 | C39—C48—H48B | 109.5 |
O1—C10—C21 | 101.2 (4) | H48A—C48—H48B | 109.5 |
O1—C10—C20 | 106.9 (4) | C39—C48—H48C | 109.5 |
C21—C10—C20 | 109.9 (5) | H48A—C48—H48C | 109.5 |
O1—C10—C9 | 114.0 (4) | H48B—C48—H48C | 109.5 |
C21—C10—C9 | 115.3 (5) | C50—C49—O14 | 111.2 (6) |
C20—C10—C9 | 109.1 (4) | C50—C49—H49 | 124.4 |
C12—C11—C5 | 110.9 (4) | O14—C49—H49 | 124.4 |
C12—C11—H11A | 109.5 | C49—C50—C51 | 104.0 (5) |
C5—C11—H11A | 109.5 | C49—C50—C43 | 127.1 (6) |
C12—C11—H11B | 109.5 | C51—C50—C43 | 128.7 (5) |
C5—C11—H11B | 109.5 | C52—C51—C50 | 107.1 (6) |
H11A—C11—H11B | 108.1 | C52—C51—H51 | 126.4 |
C11—C12—C13 | 113.4 (4) | C50—C51—H51 | 126.4 |
C11—C12—H12A | 108.9 | C51—C52—O14 | 111.9 (7) |
C13—C12—H12A | 108.9 | C51—C52—H52 | 124.1 |
C11—C12—H12B | 108.9 | O14—C52—H52 | 124.1 |
C13—C12—H12B | 108.9 | O16—C53—O15 | 117.9 (5) |
H12A—C12—H12B | 107.7 | O16—C53—C54 | 122.3 (5) |
C14—C13—C22 | 110.7 (4) | O15—C53—C54 | 119.4 (5) |
C14—C13—C12 | 109.1 (4) | C55—C54—C53 | 126.7 (5) |
C22—C13—C12 | 113.3 (4) | C55—C54—H54 | 116.7 |
C14—C13—C17 | 108.9 (4) | C53—C54—H54 | 116.7 |
C22—C13—C17 | 108.6 (5) | C54—C55—C56 | 126.6 (4) |
C12—C13—C17 | 106.1 (4) | C54—C55—H55 | 116.7 |
O4—C14—C15 | 57.8 (3) | C56—C55—H55 | 116.7 |
O4—C14—C13 | 111.0 (4) | C55—C56—C70 | 110.5 (3) |
C15—C14—C13 | 116.1 (5) | C55—C56—C57 | 105.8 (3) |
O4—C14—C6 | 114.9 (4) | C70—C56—C57 | 113.4 (4) |
C15—C14—C6 | 120.7 (5) | C55—C56—C61 | 104.7 (3) |
C13—C14—C6 | 119.7 (4) | C70—C56—C61 | 115.6 (3) |
O4—C15—C14 | 61.0 (3) | C57—C56—C61 | 106.1 (3) |
O4—C15—C16 | 116.1 (5) | C63—C57—C56 | 118.0 (3) |
C14—C15—C16 | 118.7 (6) | C63—C57—C58 | 108.0 (3) |
O4—C15—H15 | 116.5 | C56—C57—C58 | 117.1 (3) |
C14—C15—H15 | 116.5 | C63—C57—H57 | 104.0 |
C16—C15—H15 | 116.5 | C56—C57—H57 | 104.0 |
O6—C16—O5 | 120.0 (8) | C58—C57—H57 | 104.0 |
O6—C16—C15 | 119.6 (7) | C59—C58—C66 | 112.7 (3) |
O5—C16—C15 | 120.3 (6) | C59—C58—C71 | 106.6 (4) |
O5—C17—C24 | 106.3 (5) | C66—C58—C71 | 108.0 (4) |
O5—C17—C13 | 110.6 (4) | C59—C58—C57 | 106.0 (3) |
C24—C17—C13 | 115.3 (4) | C66—C58—C57 | 108.5 (3) |
O5—C17—H17 | 108.1 | C71—C58—C57 | 115.2 (4) |
C24—C17—H17 | 108.1 | O17—C59—C60 | 121.9 (4) |
C13—C17—H17 | 108.1 | O17—C59—C58 | 124.0 (4) |
C4—C18—H18A | 109.5 | C60—C59—C58 | 114.1 (4) |
C4—C18—H18B | 109.5 | C59—C60—C61 | 115.2 (4) |
H18A—C18—H18B | 109.5 | C59—C60—H60A | 108.5 |
C4—C18—H18C | 109.5 | C61—C60—H60A | 108.5 |
H18A—C18—H18C | 109.5 | C59—C60—H60B | 108.5 |
H18B—C18—H18C | 109.5 | C61—C60—H60B | 108.5 |
C6—C19—H19A | 109.5 | H60A—C60—H60B | 107.5 |
C6—C19—H19B | 109.5 | C60—C61—C56 | 114.2 (3) |
H19A—C19—H19B | 109.5 | C60—C61—C62 | 111.2 (3) |
C6—C19—H19C | 109.5 | C56—C61—C62 | 116.8 (3) |
H19A—C19—H19C | 109.5 | C60—C61—H61 | 104.3 |
H19B—C19—H19C | 109.5 | C56—C61—H61 | 104.3 |
C10—C20—H20A | 109.5 | C62—C61—H61 | 104.3 |
C10—C20—H20B | 109.5 | O15—C62—C73 | 100.2 (4) |
H20A—C20—H20B | 109.5 | O15—C62—C72 | 106.1 (4) |
C10—C20—H20C | 109.5 | C73—C62—C72 | 111.4 (5) |
H20A—C20—H20C | 109.5 | O15—C62—C61 | 115.3 (4) |
H20B—C20—H20C | 109.5 | C73—C62—C61 | 114.6 (5) |
C10—C21—H21A | 109.5 | C72—C62—C61 | 108.8 (4) |
C10—C21—H21B | 109.5 | C57—C63—C64 | 109.2 (3) |
H21A—C21—H21B | 109.5 | C57—C63—H63A | 109.8 |
C10—C21—H21C | 109.5 | C64—C63—H63A | 109.8 |
H21A—C21—H21C | 109.5 | C57—C63—H63B | 109.8 |
H21B—C21—H21C | 109.5 | C64—C63—H63B | 109.8 |
C13—C22—H22A | 109.5 | H63A—C63—H63B | 108.3 |
C13—C22—H22B | 109.5 | C63—C64—C65 | 114.5 (4) |
H22A—C22—H22B | 109.5 | C63—C64—H64A | 108.6 |
C13—C22—H22C | 109.5 | C65—C64—H64A | 108.6 |
H22A—C22—H22C | 109.5 | C63—C64—H64B | 108.6 |
H22B—C22—H22C | 109.5 | C65—C64—H64B | 108.6 |
O7—C23—C24 | 112.1 (8) | H64A—C64—H64B | 107.6 |
O7—C23—H23 | 123.9 | C66—C65—C69 | 108.0 (4) |
C24—C23—H23 | 123.9 | C66—C65—C74 | 110.7 (3) |
C23—C24—C25 | 102.8 (7) | C69—C65—C74 | 109.6 (3) |
C23—C24—C17 | 123.5 (7) | C66—C65—C64 | 108.1 (3) |
C25—C24—C17 | 133.7 (7) | C69—C65—C64 | 107.7 (3) |
C26—C25—C24 | 114.5 (9) | C74—C65—C64 | 112.7 (4) |
C26—C25—H25 | 122.8 | O18—C66—C67 | 58.9 (3) |
C24—C25—H25 | 122.8 | O18—C66—C58 | 115.7 (3) |
C25—C26—O7 | 106.7 (8) | C67—C66—C58 | 120.1 (4) |
C25—C26—H26 | 126.7 | O18—C66—C65 | 109.8 (3) |
O7—C26—H26 | 126.7 | C67—C66—C65 | 116.1 (4) |
O9—C27—O8 | 117.5 (5) | C58—C66—C65 | 119.9 (4) |
O9—C27—C28 | 121.4 (6) | O18—C67—C66 | 60.4 (3) |
O8—C27—C28 | 120.7 (5) | O18—C67—C68 | 118.7 (4) |
C29—C28—C27 | 126.6 (5) | C66—C67—C68 | 118.2 (4) |
C29—C28—H28 | 116.7 | O18—C67—H67 | 116.0 |
C27—C28—H28 | 116.7 | C66—C67—H67 | 116.0 |
C28—C29—C30 | 129.9 (4) | C68—C67—H67 | 116.0 |
C28—C29—H29 | 115.1 | O20—C68—O19 | 119.7 (5) |
C30—C29—H29 | 115.1 | O20—C68—C67 | 121.9 (5) |
C29—C30—C31 | 104.6 (3) | O19—C68—C67 | 118.2 (5) |
C29—C30—C44 | 108.2 (4) | O19—C69—C76 | 105.1 (4) |
C31—C30—C44 | 114.2 (4) | O19—C69—C65 | 110.4 (3) |
C29—C30—C35 | 106.3 (3) | C76—C69—C65 | 115.6 (4) |
C31—C30—C35 | 106.4 (3) | O19—C69—H69 | 108.5 |
C44—C30—C35 | 116.2 (4) | C76—C69—H69 | 108.5 |
C37—C31—C30 | 118.3 (3) | C65—C69—H69 | 108.5 |
C37—C31—C32 | 106.7 (3) | C56—C70—H70A | 109.5 |
C30—C31—C32 | 117.8 (3) | C56—C70—H70B | 109.5 |
C37—C31—H31 | 104.0 | H70A—C70—H70B | 109.5 |
C30—C31—H31 | 104.0 | C56—C70—H70C | 109.5 |
C32—C31—H31 | 104.0 | H70A—C70—H70C | 109.5 |
C33—C32—C45 | 107.9 (4) | H70B—C70—H70C | 109.5 |
C33—C32—C31 | 104.7 (3) | C58—C71—H71A | 109.5 |
C45—C32—C31 | 114.6 (4) | C58—C71—H71B | 109.5 |
C33—C32—C40 | 113.5 (4) | H71A—C71—H71B | 109.5 |
C45—C32—C40 | 107.8 (4) | C58—C71—H71C | 109.5 |
C31—C32—C40 | 108.5 (3) | H71A—C71—H71C | 109.5 |
O10—C33—C34 | 121.1 (4) | H71B—C71—H71C | 109.5 |
O10—C33—C32 | 123.6 (4) | C62—C72—H72A | 109.5 |
C34—C33—C32 | 115.3 (4) | C62—C72—H72B | 109.5 |
C33—C34—C35 | 115.1 (4) | H72A—C72—H72B | 109.5 |
C33—C34—H34A | 108.5 | C62—C72—H72C | 109.5 |
C35—C34—H34A | 108.5 | H72A—C72—H72C | 109.5 |
C33—C34—H34B | 108.5 | H72B—C72—H72C | 109.5 |
C35—C34—H34B | 108.5 | C62—C73—H73A | 109.5 |
H34A—C34—H34B | 107.5 | C62—C73—H73B | 109.5 |
C34—C35—C36 | 109.9 (3) | H73A—C73—H73B | 109.5 |
C34—C35—C30 | 114.2 (3) | C62—C73—H73C | 109.5 |
C36—C35—C30 | 117.9 (4) | H73A—C73—H73C | 109.5 |
C34—C35—H35 | 104.4 | H73B—C73—H73C | 109.5 |
C36—C35—H35 | 104.4 | C65—C74—H74A | 109.5 |
C30—C35—H35 | 104.4 | C65—C74—H74B | 109.5 |
O8—C36—C47 | 101.1 (4) | H74A—C74—H74B | 109.5 |
O8—C36—C46 | 107.0 (4) | C65—C74—H74C | 109.5 |
C47—C36—C46 | 110.2 (4) | H74A—C74—H74C | 109.5 |
O8—C36—C35 | 112.4 (3) | H74B—C74—H74C | 109.5 |
C47—C36—C35 | 115.6 (4) | C76—C75—O21 | 110.8 (5) |
C46—C36—C35 | 110.0 (4) | C76—C75—H75 | 124.6 |
C38—C37—C31 | 108.2 (4) | O21—C75—H75 | 124.6 |
C38—C37—H37A | 110.1 | C75—C76—C77 | 106.2 (5) |
C31—C37—H37A | 110.1 | C75—C76—C69 | 125.0 (5) |
C38—C37—H37B | 110.1 | C77—C76—C69 | 128.8 (5) |
C31—C37—H37B | 110.1 | C78—C77—C76 | 107.2 (6) |
H37A—C37—H37B | 108.4 | C78—C77—H77 | 126.4 |
C37—C38—C39 | 114.6 (3) | C76—C77—H77 | 126.4 |
C37—C38—H38A | 108.6 | C77—C78—O21 | 109.2 (5) |
C39—C38—H38A | 108.6 | C77—C78—H78 | 125.4 |
C37—C38—H38B | 108.6 | O21—C78—H78 | 125.4 |
C39—C38—H38B | 108.6 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18A···O1 | 0.96 | 2.46 | 3.041 (7) | 119 |
C22—H22A···O5 | 0.96 | 2.55 | 2.970 (6) | 107 |
C44—H44B···O8 | 0.96 | 2.49 | 3.033 (6) | 116 |
C55—H55···O13 | 0.93 | 2.52 | 3.312 (5) | 143 |
C61—H61···O10 | 0.97 | 2.57 | 3.448 (4) | 149 |
C64—H64B···O13 | 0.97 | 2.57 | 3.403 (6) | 144 |
C70—H70C···O15 | 0.96 | 2.56 | 2.925 (5) | 103 |
C74—H74A···O19 | 0.96 | 2.55 | 2.964 (5) | 106 |
C9—H9···O17i | 0.98 | 2.53 | 3.460 (6) | 159 |
C22—H22C···O17i | 0.96 | 2.58 | 3.439 (6) | 149 |
C23—H23···O2ii | 0.93 | 2.48 | 3.188 (8) | 133 |
C37—H37B···O19i | 0.97 | 2.57 | 3.424 (5) | 147 |
C37—H37B···O20i | 0.97 | 2.58 | 3.299 (5) | 131 |
C72—H72A···O8iii | 0.96 | 2.56 | 3.409 (7) | 148 |
C73—H73B···O21iv | 0.96 | 2.55 | 3.430 (7) | 152 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x+1, y, z; (iii) x+1/2, −y+1/2, −z+1; (iv) −x+3/2, −y+1, z−1/2. |
Puckering parameters (Å, °) for seven- and six-membered rings. top | q2 | q3 | φ2 | φ3 | Q | θ2 |
Molecule 1 | | | | | | |
ring A | 0.821 (4) | 0.273 (4) | -20.1 (3) | 75.6 (10) | 0.866 (4) | 71.6 (3) |
ring B | 0.053 (4) | 0.528 (4) | 103 (5) | | 0.503 (4) | 5.8 (4) |
ring C | 0.755 (5) | -0.102 (5) | -159.5 (3) | | 0.764 (5) | 97.7 (4) |
ring D | 0.495 (6) | -0.190 (6) | 97.4 (6) | | 0.530 (6) | 111.0 (7) |
Molecule 2 | | | | | | |
ring A | 0.816 (4) | 0.301 (5) | -16.2 (4) | 70.8 (8) | 0.870 (4) | 69.8 (3) |
ring B | 0.100 (4) | 0.527 (4) | 87 (3) | | 0.536 (4) | 10.7 (4) |
ring C | 0.778 (5) | -0.108 (4) | -152.0 (3) | | 0.786 (5) | 97.9 (3) |
ring D | 0.480 (5) | -0.200 (4) | 96.6 (6) | | 0.520 (5) | 112.7 (5) |
Molecule 3 | | | | | | |
ring A | 0.901 (4) | 0.240 (4) | -36.3 (3) | 78.2 (10) | 0.932 (4) | 75.1 (2) |
ring B | 0.085 (4) | 0.536 (4) | 76 (3) | | 0.542 (4) | 9.0 (4) |
ring C | 0.757 (4) | -0.099 (4) | -154.7 (3) | | 0.763 (4) | 97.5 (3) |
ring D | 0.537 (4) | -0.166 (4) | 95.7 (4) | | 0.562 (4) | 107.2 (4) |