The title compound, 4-(3-furyl)-1,4,4a,5,6,6a,7,8α,9,10,11α,12-dodecahydro-4a,7,9,9-tetramethyl-2,10,13-trioxo-7,11-methano-2
H-cycloocta[
f][2]benzopyran-8-hydroxyacetic acid methyl ester (C
27H
32O
8), has for the first time been isolated from
Lansium domesticum, Correa. The six-membered rings adopt boat, chair, distorted sofa and half-chair conformations. The furan ring is planar. The furan substituent and hydroxyacetate group are attached equatorially to the swietenine skeleton. The crystal structure is stabilized by C—H
O interactions.
Supporting information
CCDC reference: 234924
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.050
- wR factor = 0.134
- Data-to-parameter ratio = 8.6
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.02 Ratio
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.47 Ratio
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.68 Ratio
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... O8
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT482_ALERT_4_C Small D-H..A Angle Rep for O6 .. O7 = 98.00 Deg.
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 26.00
From the CIF: _reflns_number_total 2744
Count of symmetry unique reflns 2751
Completeness (_total/calc) 99.75%
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
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 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
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
4-(3-Furyl)-1,4,4a,5,6,6a,7,8
α,9,10,11
α,12-dodecahydro-4a,7,9,9-
tetramethyl-2,10,13-trioxo-7,11-methano-2
H-cycloocta[
f][2]benzopyran-8- hydroxyl acetic acid methyl ester
top
Crystal data top
C27H32O8 | Dx = 1.312 Mg m−3 |
Mr = 484.53 | Melting point: 537-538 K K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5306 reflections |
a = 10.6293 (6) Å | θ = 2.7–26.0° |
b = 10.7405 (6) Å | µ = 0.10 mm−1 |
c = 21.4937 (13) Å | T = 293 K |
V = 2453.8 (2) Å3 | Block, colorless |
Z = 4 | 0.30 × 0.28 × 0.22 mm |
F(000) = 1032 | |
Data collection top
Siemens SMART CCD area detector diffractometer | 2744 independent reflections |
Radiation source: fine-focus sealed tube | 2249 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.0°, θmin = 2.7° |
ω scan | h = −12→13 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −13→11 |
Tmin = 0.972, Tmax = 0.979 | l = −19→26 |
13401 measured 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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0595P)2 + 0.8864P] where P = (Fo2 + 2Fc2)/3 |
2744 reflections | (Δ/σ)max < 0.001 |
320 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
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 | 0.7541 (3) | 0.6472 (3) | 1.06214 (12) | 0.0782 (10) | |
O2 | 0.7735 (4) | 0.2693 (3) | 0.96655 (14) | 0.0830 (11) | |
O3 | 0.3419 (2) | 0.3443 (2) | 0.79085 (11) | 0.0500 (6) | |
O4 | 0.2483 (3) | 0.2119 (3) | 0.85196 (14) | 0.0754 (9) | |
O5 | 0.4332 (4) | 0.5765 (4) | 0.62604 (14) | 0.0885 (11) | |
O6 | 0.9758 (3) | 0.6963 (4) | 0.8729 (2) | 0.1019 (13) | |
H6B | 1.0093 | 0.7359 | 0.8448 | 0.153* | |
O7 | 0.9975 (4) | 0.5815 (6) | 0.7662 (2) | 0.134 (2) | |
O8 | 0.8028 (4) | 0.5039 (3) | 0.76861 (13) | 0.0809 (11) | |
C1 | 0.7377 (4) | 0.5884 (4) | 1.01519 (17) | 0.0531 (9) | |
C2 | 0.7303 (4) | 0.6470 (3) | 0.95065 (16) | 0.0469 (9) | |
C3 | 0.7981 (3) | 0.5618 (3) | 0.90090 (15) | 0.0438 (8) | |
H3A | 0.7293 | 0.5191 | 0.8793 | 0.053* | |
C4 | 0.8781 (4) | 0.4544 (4) | 0.93042 (17) | 0.0557 (10) | |
C5 | 0.7845 (5) | 0.3800 (4) | 0.96961 (16) | 0.0566 (11) | |
C6 | 0.7049 (4) | 0.4537 (4) | 1.01569 (15) | 0.0554 (10) | |
H6A | 0.7182 | 0.4204 | 1.0576 | 0.066* | |
C7 | 0.5633 (4) | 0.4441 (4) | 0.99908 (17) | 0.0622 (11) | |
H7A | 0.5414 | 0.3573 | 0.9928 | 0.075* | |
H7B | 0.5137 | 0.4751 | 1.0336 | 0.075* | |
C8 | 0.5306 (3) | 0.5171 (3) | 0.94094 (15) | 0.0437 (8) | |
C9 | 0.5821 (3) | 0.6478 (3) | 0.93964 (15) | 0.0429 (8) | |
H9A | 0.5464 | 0.6891 | 0.9763 | 0.052* | |
C10 | 0.5366 (3) | 0.7240 (3) | 0.88395 (16) | 0.0452 (8) | |
H10A | 0.5988 | 0.7874 | 0.8746 | 0.054* | |
H10B | 0.4592 | 0.7661 | 0.8953 | 0.054* | |
C11 | 0.5133 (3) | 0.6467 (3) | 0.82536 (15) | 0.0396 (7) | |
H11A | 0.5923 | 0.6121 | 0.8109 | 0.047* | |
H11B | 0.4802 | 0.7000 | 0.7928 | 0.047* | |
C12 | 0.4203 (3) | 0.5408 (3) | 0.83784 (14) | 0.0363 (7) | |
C13 | 0.4566 (3) | 0.4704 (3) | 0.89614 (14) | 0.0394 (7) | |
C14 | 0.3990 (4) | 0.3408 (4) | 0.90081 (18) | 0.0565 (10) | |
H14A | 0.4668 | 0.2820 | 0.9079 | 0.068* | |
H14B | 0.3456 | 0.3390 | 0.9374 | 0.068* | |
C15 | 0.3238 (4) | 0.2949 (3) | 0.84732 (18) | 0.0500 (9) | |
C16 | 0.4305 (3) | 0.4468 (3) | 0.78374 (14) | 0.0396 (7) | |
H16A | 0.5159 | 0.4124 | 0.7836 | 0.048* | |
C17 | 0.4037 (4) | 0.4990 (3) | 0.72052 (16) | 0.0473 (9) | |
C18 | 0.2850 (5) | 0.5232 (4) | 0.69302 (19) | 0.0663 (12) | |
H18A | 0.2064 | 0.5092 | 0.7107 | 0.080* | |
C19 | 0.3085 (6) | 0.5699 (5) | 0.6369 (2) | 0.0833 (16) | |
H19A | 0.2469 | 0.5948 | 0.6088 | 0.100* | |
C20 | 0.4890 (5) | 0.5308 (5) | 0.67796 (18) | 0.0682 (12) | |
H20A | 0.5755 | 0.5227 | 0.6832 | 0.082* | |
C21 | 0.2856 (3) | 0.5902 (4) | 0.84450 (18) | 0.0484 (8) | |
H21A | 0.2820 | 0.6484 | 0.8783 | 0.073* | |
H21B | 0.2295 | 0.5220 | 0.8527 | 0.073* | |
H21C | 0.2610 | 0.6309 | 0.8067 | 0.073* | |
C22 | 0.7787 (4) | 0.7816 (4) | 0.9552 (2) | 0.0654 (12) | |
H22A | 0.8653 | 0.7811 | 0.9679 | 0.098* | |
H22B | 0.7296 | 0.8265 | 0.9853 | 0.098* | |
H22C | 0.7713 | 0.8213 | 0.9154 | 0.098* | |
C23 | 0.9862 (4) | 0.4987 (5) | 0.9740 (2) | 0.0781 (14) | |
H23A | 1.0238 | 0.4278 | 0.9939 | 0.117* | |
H23B | 0.9529 | 0.5538 | 1.0050 | 0.117* | |
H23C | 1.0487 | 0.5416 | 0.9499 | 0.117* | |
C24 | 0.9349 (5) | 0.3674 (5) | 0.8816 (2) | 0.0779 (14) | |
H24A | 0.9724 | 0.2970 | 0.9019 | 0.117* | |
H24B | 0.9980 | 0.4113 | 0.8584 | 0.117* | |
H24C | 0.8700 | 0.3394 | 0.8539 | 0.117* | |
C25 | 0.8644 (4) | 0.6379 (4) | 0.8499 (2) | 0.0628 (11) | |
H25A | 0.8066 | 0.7050 | 0.8382 | 0.075* | |
C26 | 0.8978 (5) | 0.5722 (6) | 0.7916 (2) | 0.0828 (15) | |
C27 | 0.8347 (8) | 0.4385 (7) | 0.7111 (3) | 0.126 (3) | |
H27A | 0.7589 | 0.4146 | 0.6900 | 0.189* | |
H27B | 0.8831 | 0.3655 | 0.7208 | 0.189* | |
H27C | 0.8832 | 0.4924 | 0.6848 | 0.189* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.113 (3) | 0.075 (2) | 0.0464 (15) | −0.012 (2) | −0.0217 (16) | −0.0166 (15) |
O2 | 0.143 (3) | 0.0467 (17) | 0.0596 (17) | −0.006 (2) | −0.017 (2) | 0.0008 (14) |
O3 | 0.0635 (15) | 0.0400 (13) | 0.0466 (13) | −0.0113 (12) | 0.0009 (12) | −0.0023 (11) |
O4 | 0.089 (2) | 0.0607 (18) | 0.0764 (19) | −0.0366 (18) | −0.0016 (17) | 0.0090 (16) |
O5 | 0.127 (3) | 0.091 (3) | 0.0480 (17) | −0.018 (3) | 0.004 (2) | 0.0183 (16) |
O6 | 0.0556 (18) | 0.112 (3) | 0.139 (3) | −0.024 (2) | −0.003 (2) | 0.037 (3) |
O7 | 0.089 (3) | 0.195 (5) | 0.117 (4) | 0.048 (3) | 0.061 (3) | 0.048 (3) |
O8 | 0.098 (3) | 0.098 (3) | 0.0461 (16) | 0.048 (2) | 0.0099 (16) | −0.0005 (16) |
C1 | 0.059 (2) | 0.057 (2) | 0.0426 (19) | −0.002 (2) | −0.0109 (18) | −0.0072 (17) |
C2 | 0.054 (2) | 0.0411 (19) | 0.0458 (19) | −0.0041 (18) | −0.0150 (16) | −0.0032 (15) |
C3 | 0.0421 (17) | 0.0463 (19) | 0.0429 (17) | 0.0025 (16) | −0.0068 (15) | 0.0044 (16) |
C4 | 0.065 (2) | 0.054 (2) | 0.048 (2) | 0.012 (2) | −0.0146 (18) | 0.0030 (18) |
C5 | 0.086 (3) | 0.049 (2) | 0.0344 (18) | 0.001 (2) | −0.030 (2) | 0.0034 (16) |
C6 | 0.081 (3) | 0.057 (2) | 0.0279 (15) | −0.008 (2) | −0.0158 (18) | 0.0084 (16) |
C7 | 0.081 (3) | 0.065 (3) | 0.0404 (19) | −0.019 (2) | −0.0024 (19) | 0.0118 (19) |
C8 | 0.0499 (19) | 0.047 (2) | 0.0346 (16) | −0.0040 (17) | 0.0062 (15) | 0.0041 (15) |
C9 | 0.0505 (19) | 0.0418 (19) | 0.0365 (16) | 0.0001 (17) | 0.0047 (15) | −0.0038 (14) |
C10 | 0.0454 (18) | 0.0337 (17) | 0.056 (2) | 0.0015 (16) | −0.0024 (17) | −0.0002 (15) |
C11 | 0.0408 (17) | 0.0360 (17) | 0.0420 (17) | −0.0016 (15) | −0.0029 (14) | 0.0082 (14) |
C12 | 0.0356 (15) | 0.0365 (16) | 0.0367 (15) | 0.0002 (14) | 0.0065 (13) | 0.0012 (14) |
C13 | 0.0423 (17) | 0.0381 (17) | 0.0377 (16) | −0.0034 (15) | 0.0076 (14) | 0.0008 (14) |
C14 | 0.070 (2) | 0.047 (2) | 0.052 (2) | −0.015 (2) | −0.0014 (19) | 0.0129 (18) |
C15 | 0.059 (2) | 0.0356 (18) | 0.056 (2) | −0.0054 (18) | 0.0034 (18) | 0.0012 (16) |
C16 | 0.0434 (17) | 0.0344 (17) | 0.0411 (16) | 0.0002 (15) | 0.0057 (15) | −0.0005 (14) |
C17 | 0.059 (2) | 0.042 (2) | 0.0408 (18) | −0.0022 (17) | 0.0023 (17) | −0.0030 (15) |
C18 | 0.073 (3) | 0.074 (3) | 0.052 (2) | 0.003 (3) | −0.010 (2) | 0.000 (2) |
C19 | 0.121 (5) | 0.072 (3) | 0.056 (3) | 0.007 (3) | −0.028 (3) | 0.004 (2) |
C20 | 0.085 (3) | 0.074 (3) | 0.046 (2) | −0.014 (3) | 0.006 (2) | 0.008 (2) |
C21 | 0.0409 (18) | 0.052 (2) | 0.052 (2) | 0.0024 (17) | 0.0013 (16) | −0.0086 (17) |
C22 | 0.070 (3) | 0.048 (2) | 0.078 (3) | −0.012 (2) | −0.023 (2) | −0.003 (2) |
C23 | 0.066 (3) | 0.085 (3) | 0.083 (3) | 0.008 (3) | −0.034 (2) | 0.007 (3) |
C24 | 0.089 (3) | 0.076 (3) | 0.069 (3) | 0.040 (3) | −0.007 (3) | 0.007 (2) |
C25 | 0.042 (2) | 0.073 (3) | 0.073 (3) | 0.007 (2) | 0.0048 (19) | 0.024 (2) |
C26 | 0.075 (3) | 0.102 (4) | 0.071 (3) | 0.031 (3) | 0.011 (3) | 0.024 (3) |
C27 | 0.174 (7) | 0.132 (6) | 0.072 (3) | 0.065 (6) | −0.001 (4) | −0.018 (4) |
Geometric parameters (Å, º) top
C11—C10 | 1.529 (5) | C24—C4 | 1.529 (6) |
C11—C12 | 1.531 (4) | C24—H24A | 0.96 |
C11—H11A | 0.97 | C24—H24B | 0.96 |
C11—H11B | 0.97 | C24—H24C | 0.96 |
C12—C13 | 1.513 (4) | C25—O6 | 1.428 (5) |
C12—C21 | 1.534 (5) | C25—C26 | 1.480 (7) |
C12—C16 | 1.543 (4) | C25—C3 | 1.539 (5) |
C13—C8 | 1.341 (5) | C25—H25A | 0.98 |
C13—C14 | 1.524 (5) | C26—O7 | 1.197 (6) |
C14—C15 | 1.484 (5) | C26—O8 | 1.342 (7) |
C14—H14A | 0.97 | C27—O8 | 1.462 (6) |
C14—H14B | 0.97 | C27—H27A | 0.96 |
C15—O4 | 1.204 (4) | C27—H27B | 0.96 |
C15—O3 | 1.338 (4) | C27—H27C | 0.96 |
C16—O3 | 1.457 (4) | O1—C1 | 1.203 (4) |
C16—C17 | 1.497 (5) | O2—C5 | 1.197 (5) |
C16—H16A | 0.98 | O6—H6B | 0.82 |
C17—C20 | 1.332 (6) | C1—C6 | 1.487 (6) |
C17—C18 | 1.417 (6) | C1—C2 | 1.526 (5) |
C18—C19 | 1.330 (6) | C2—C3 | 1.581 (5) |
C18—H18A | 0.93 | C2—C9 | 1.593 (5) |
C19—O5 | 1.347 (7) | C3—C4 | 1.568 (5) |
C19—H19A | 0.93 | C3—H3A | 0.98 |
C20—O5 | 1.356 (5) | C4—C5 | 1.529 (6) |
C20—H20A | 0.93 | C5—C6 | 1.524 (6) |
C21—H21A | 0.96 | C6—C7 | 1.551 (6) |
C21—H21B | 0.96 | C6—H6A | 0.98 |
C21—H21C | 0.96 | C7—C8 | 1.516 (5) |
C22—C2 | 1.537 (5) | C7—H7A | 0.97 |
C22—H22A | 0.96 | C7—H7B | 0.97 |
C22—H22B | 0.96 | C8—C9 | 1.507 (5) |
C22—H22C | 0.96 | C9—C10 | 1.528 (5) |
C23—C4 | 1.557 (6) | C9—H9A | 0.98 |
C23—H23A | 0.96 | C10—H10A | 0.97 |
C23—H23B | 0.96 | C10—H10B | 0.97 |
C23—H23C | 0.96 | | |
| | | |
C10—C11—C12 | 111.4 (3) | C26—C25—C3 | 117.4 (4) |
C10—C11—H11A | 109.4 | O6—C25—H25A | 106.6 |
C12—C11—H11A | 109.4 | C26—C25—H25A | 106.6 |
C10—C11—H11B | 109.4 | C3—C25—H25A | 106.6 |
C12—C11—H11B | 109.4 | O7—C26—O8 | 122.9 (6) |
H11A—C11—H11B | 108.0 | O7—C26—C25 | 124.0 (6) |
C13—C12—C11 | 110.6 (3) | O8—C26—C25 | 113.1 (4) |
C13—C12—C21 | 109.5 (3) | O8—C27—H27A | 109.5 |
C11—C12—C21 | 111.2 (3) | O8—C27—H27B | 109.5 |
C13—C12—C16 | 106.2 (3) | H27A—C27—H27B | 109.5 |
C11—C12—C16 | 107.9 (2) | O8—C27—H27C | 109.5 |
C21—C12—C16 | 111.3 (3) | H27A—C27—H27C | 109.5 |
C8—C13—C12 | 123.9 (3) | H27B—C27—H27C | 109.5 |
C8—C13—C14 | 122.0 (3) | C15—O3—C16 | 119.2 (3) |
C12—C13—C14 | 114.1 (3) | C19—O5—C20 | 105.6 (4) |
C15—C14—C13 | 117.9 (3) | C25—O6—H6B | 109.5 |
C15—C14—H14A | 107.8 | C26—O8—C27 | 113.6 (5) |
C13—C14—H14A | 107.8 | O1—C1—C6 | 122.6 (4) |
C15—C14—H14B | 107.8 | O1—C1—C2 | 123.6 (4) |
C13—C14—H14B | 107.8 | C6—C1—C2 | 113.3 (3) |
H14A—C14—H14B | 107.2 | C1—C2—C22 | 108.2 (3) |
O4—C15—O3 | 117.7 (3) | C1—C2—C3 | 110.6 (3) |
O4—C15—C14 | 122.7 (3) | C22—C2—C3 | 115.8 (3) |
O3—C15—C14 | 119.6 (3) | C1—C2—C9 | 100.8 (3) |
O3—C16—C17 | 104.7 (3) | C22—C2—C9 | 109.6 (3) |
O3—C16—C12 | 111.7 (2) | C3—C2—C9 | 110.7 (3) |
C17—C16—C12 | 115.2 (3) | C25—C3—C4 | 115.5 (3) |
O3—C16—H16A | 108.3 | C25—C3—C2 | 112.6 (3) |
C17—C16—H16A | 108.3 | C4—C3—C2 | 113.6 (3) |
C12—C16—H16A | 108.3 | C25—C3—H3A | 104.6 |
C20—C17—C18 | 105.8 (4) | C4—C3—H3A | 104.6 |
C20—C17—C16 | 126.1 (4) | C2—C3—H3A | 104.6 |
C18—C17—C16 | 128.1 (3) | C24—C4—C5 | 108.4 (4) |
C19—C18—C17 | 106.3 (5) | C24—C4—C23 | 107.9 (4) |
C19—C18—H18A | 126.9 | C5—C4—C23 | 108.0 (3) |
C17—C18—H18A | 126.9 | C24—C4—C3 | 112.7 (3) |
C18—C19—O5 | 111.2 (4) | C5—C4—C3 | 104.7 (3) |
C18—C19—H19A | 124.4 | C23—C4—C3 | 114.8 (3) |
O5—C19—H19A | 124.4 | O2—C5—C6 | 119.8 (4) |
C17—C20—O5 | 111.1 (4) | O2—C5—C4 | 123.5 (4) |
C17—C20—H20A | 124.4 | C6—C5—C4 | 116.6 (3) |
O5—C20—H20A | 124.4 | C1—C6—C5 | 111.7 (4) |
C12—C21—H21A | 109.5 | C1—C6—C7 | 106.9 (4) |
C12—C21—H21B | 109.5 | C5—C6—C7 | 110.8 (3) |
H21A—C21—H21B | 109.5 | C1—C6—H6A | 109.1 |
C12—C21—H21C | 109.5 | C5—C6—H6A | 109.1 |
H21A—C21—H21C | 109.5 | C7—C6—H6A | 109.1 |
H21B—C21—H21C | 109.5 | C8—C7—C6 | 112.2 (3) |
C2—C22—H22A | 109.5 | C8—C7—H7A | 109.2 |
C2—C22—H22B | 109.5 | C6—C7—H7A | 109.2 |
H22A—C22—H22B | 109.5 | C8—C7—H7B | 109.2 |
C2—C22—H22C | 109.5 | C6—C7—H7B | 109.2 |
H22A—C22—H22C | 109.5 | H7A—C7—H7B | 107.9 |
H22B—C22—H22C | 109.5 | C13—C8—C9 | 123.3 (3) |
C4—C23—H23A | 109.5 | C13—C8—C7 | 122.2 (3) |
C4—C23—H23B | 109.5 | C9—C8—C7 | 114.5 (3) |
H23A—C23—H23B | 109.5 | C8—C9—C10 | 113.5 (3) |
C4—C23—H23C | 109.5 | C8—C9—C2 | 110.6 (3) |
H23A—C23—H23C | 109.5 | C10—C9—C2 | 115.6 (3) |
H23B—C23—H23C | 109.5 | C8—C9—H9A | 105.4 |
C4—C24—H24A | 109.5 | C10—C9—H9A | 105.4 |
C4—C24—H24B | 109.5 | C2—C9—H9A | 105.4 |
H24A—C24—H24B | 109.5 | C9—C10—C11 | 113.9 (3) |
C4—C24—H24C | 109.5 | C9—C10—H10A | 108.8 |
H24A—C24—H24C | 109.5 | C11—C10—H10A | 108.8 |
H24B—C24—H24C | 109.5 | C9—C10—H10B | 108.8 |
O6—C25—C26 | 107.7 (4) | C11—C10—H10B | 108.8 |
O6—C25—C3 | 111.5 (3) | H10A—C10—H10B | 107.7 |
| | | |
C10—C11—C12—C13 | −48.3 (4) | C26—C25—C3—C2 | −162.2 (4) |
C10—C11—C12—C21 | 73.6 (4) | C1—C2—C3—C25 | −145.1 (3) |
C10—C11—C12—C16 | −164.1 (3) | C22—C2—C3—C25 | −21.5 (4) |
C11—C12—C13—C8 | 20.7 (4) | C9—C2—C3—C25 | 104.0 (3) |
C21—C12—C13—C8 | −102.2 (4) | C1—C2—C3—C4 | −11.5 (4) |
C16—C12—C13—C8 | 137.6 (3) | C22—C2—C3—C4 | 112.1 (4) |
C11—C12—C13—C14 | −160.6 (3) | C9—C2—C3—C4 | −122.4 (3) |
C21—C12—C13—C14 | 76.5 (4) | C25—C3—C4—C24 | −52.0 (5) |
C16—C12—C13—C14 | −43.7 (4) | C2—C3—C4—C24 | 175.8 (4) |
C8—C13—C14—C15 | −176.9 (3) | C25—C3—C4—C5 | −169.7 (3) |
C12—C13—C14—C15 | 4.4 (5) | C2—C3—C4—C5 | 58.1 (4) |
C13—C14—C15—O4 | −159.6 (4) | C25—C3—C4—C23 | 72.1 (5) |
C13—C14—C15—O3 | 22.4 (5) | C2—C3—C4—C23 | −60.1 (4) |
C13—C12—C16—O3 | 63.2 (3) | C24—C4—C5—O2 | 9.2 (5) |
C11—C12—C16—O3 | −178.2 (3) | C23—C4—C5—O2 | −107.5 (5) |
C21—C12—C16—O3 | −55.9 (4) | C3—C4—C5—O2 | 129.8 (4) |
C13—C12—C16—C17 | −177.5 (3) | C24—C4—C5—C6 | −172.4 (3) |
C11—C12—C16—C17 | −58.9 (4) | C23—C4—C5—C6 | 70.9 (4) |
C21—C12—C16—C17 | 63.5 (4) | C3—C4—C5—C6 | −51.8 (4) |
O3—C16—C17—C20 | −135.3 (4) | O1—C1—C6—C5 | −133.4 (4) |
C12—C16—C17—C20 | 101.6 (4) | C2—C1—C6—C5 | 54.6 (5) |
O3—C16—C17—C18 | 43.7 (5) | O1—C1—C6—C7 | 105.3 (5) |
C12—C16—C17—C18 | −79.4 (5) | C2—C1—C6—C7 | −66.8 (4) |
C20—C17—C18—C19 | −1.3 (5) | O2—C5—C6—C1 | 176.5 (4) |
C16—C17—C18—C19 | 179.5 (4) | C4—C5—C6—C1 | −2.0 (5) |
C17—C18—C19—O5 | 0.6 (6) | O2—C5—C6—C7 | −64.4 (5) |
C18—C17—C20—O5 | 1.6 (5) | C4—C5—C6—C7 | 117.1 (4) |
C16—C17—C20—O5 | −179.2 (3) | C1—C6—C7—C8 | 50.3 (4) |
O6—C25—C26—O7 | −8.0 (7) | C5—C6—C7—C8 | −71.6 (4) |
C3—C25—C26—O7 | −134.8 (5) | C12—C13—C8—C9 | 2.6 (5) |
O6—C25—C26—O8 | 174.2 (4) | C14—C13—C8—C9 | −175.9 (3) |
C3—C25—C26—O8 | 47.5 (5) | C12—C13—C8—C7 | 179.2 (3) |
O4—C15—O3—C16 | 178.7 (3) | C14—C13—C8—C7 | 0.6 (5) |
C14—C15—O3—C16 | −3.2 (5) | C6—C7—C8—C13 | 135.5 (4) |
C17—C16—O3—C15 | −166.1 (3) | C6—C7—C8—C9 | −47.7 (5) |
C12—C16—O3—C15 | −40.8 (4) | C13—C8—C9—C10 | 2.8 (5) |
C18—C19—O5—C20 | 0.4 (6) | C7—C8—C9—C10 | −173.9 (3) |
C17—C20—O5—C19 | −1.3 (6) | C13—C8—C9—C2 | −128.9 (4) |
O7—C26—O8—C27 | 2.3 (7) | C7—C8—C9—C2 | 54.3 (4) |
C25—C26—O8—C27 | −179.9 (4) | C1—C2—C9—C8 | −60.8 (3) |
O1—C1—C2—C22 | 13.6 (6) | C22—C2—C9—C8 | −174.7 (3) |
C6—C1—C2—C22 | −174.4 (4) | C3—C2—C9—C8 | 56.3 (4) |
O1—C1—C2—C3 | 141.5 (4) | C1—C2—C9—C10 | 168.6 (3) |
C6—C1—C2—C3 | −46.6 (4) | C22—C2—C9—C10 | 54.6 (4) |
O1—C1—C2—C9 | −101.4 (5) | C3—C2—C9—C10 | −74.3 (4) |
C6—C1—C2—C9 | 70.6 (4) | C8—C9—C10—C11 | −32.0 (4) |
O6—C25—C3—C4 | −59.7 (5) | C2—C9—C10—C11 | 97.3 (4) |
C26—C25—C3—C4 | 65.2 (5) | C12—C11—C10—C9 | 55.8 (4) |
O6—C25—C3—C2 | 73.0 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···O8 | 0.98 | 2.51 | 2.911 (4) | 104 |
C6—H6A···O4i | 0.98 | 2.43 | 3.387 (5) | 166 |
C10—H10B···O1ii | 0.97 | 2.54 | 3.503 (5) | 172 |
C14—H14A···O5iii | 0.97 | 2.56 | 3.402 (6) | 146 |
C14—H14B···O2iv | 0.97 | 2.49 | 3.362 (5) | 149 |
C19—H19A···O2v | 0.93 | 2.49 | 3.208 (6) | 135 |
C21—H21A···O1ii | 0.96 | 2.56 | 3.478 (5) | 161 |
C22—H22A···O6 | 0.96 | 2.53 | 2.891 (6) | 103 |
C23—H23C···O6 | 0.96 | 2.47 | 3.039 (6) | 118 |
O6—H6B···O7 | 0.82 | 2.37 | 2.614 (6) | 98 |
Symmetry codes: (i) x+1/2, −y+1/2, −z+2; (ii) x−1/2, −y+3/2, −z+2; (iii) −x+1, y−1/2, −z+3/2; (iv) x−1/2, −y+1/2, −z+2; (v) −x+1, y+1/2, −z+3/2. |