The title compound, (
E)-3-[2-(3,3,6a,10
b-tetramethyl-8-methyleneperhydronaphtho[2,1-
d][1,3]dioxin-7-yl)vinyl]furan-2(5
H)-one, C
23H
32O
4, an andrographolide analogue, was semi-synthesized from 14-deoxy-11,12-didehydroandrographolide. All the six-membered rings in the structure adopt chair conformations. The crystal structure is stabilized by C—H
O interactions, which form a two-dimensional network parallel to the
ab plane
Supporting information
CCDC reference: 298397
checkCIF/PLATON results
No syntax errors found
Datablock: I
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.825 0.984
Tmin(prime) and Tmax expected: 0.958 0.984
RR(prime) = 0.861
Please check that your absorption correction is appropriate.
ABSTY02_ALERT_1_C An _exptl_absorpt_correction_type has been given without
a literature citation. This should be contained in the
_exptl_absorpt_process_details field.
Absorption correction given as multi-scan
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.86
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 30.03
From the CIF: _reflns_number_total 3452
Count of symmetry unique reflns 3456
Completeness (_total/calc) 99.88%
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
0 ALERT level B = Potentially serious problem
3 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
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
1 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
Please specify the role of each of the co-authors
for your paper.
| Author Response: H.K. Fun and I.A. Razak are supervisors
of Jeannie B.-J. Teh whereas J. Stanslas is
supervisor of S. R. Sagineedu and N. H. Lajis in this collaborative
pulication. UPM is involved in the extraction and synthesis
of the title compound and USM is involved in the structure
determination. All parties are involved in writing up the
manuscript.
|
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
(
E)-3-[2-(3,3,6a,10
b-tetramethyl-8-methyleneperhydronaphtho[2,1-
d][1,3]dioxin- 7-yl)vinyl]furan-2(5
H)-one
top
Crystal data top
C23H32O4 | F(000) = 808 |
Mr = 372.49 | Dx = 1.184 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 7069 reflections |
a = 9.1528 (2) Å | θ = 1.9–30.0° |
b = 10.3440 (2) Å | µ = 0.08 mm−1 |
c = 22.0663 (4) Å | T = 297 K |
V = 2089.16 (7) Å3 | Rod, colourless |
Z = 4 | 0.54 × 0.21 × 0.21 mm |
Data collection top
Bruker SMART APEX2 CCD area-detector diffractometer | 3452 independent reflections |
Radiation source: fine-focus sealed tube | 2173 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 8.33 pixels mm-1 | θmax = 30.0°, θmin = 1.9° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −14→14 |
Tmin = 0.825, Tmax = 0.984 | l = −31→31 |
27503 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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0499P)2 + 0.0866P] where P = (Fo2 + 2Fc2)/3 |
3452 reflections | (Δ/σ)max = 0.001 |
248 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.13 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 | 0.13560 (16) | 1.07224 (14) | 0.06345 (6) | 0.0628 (4) | |
O2 | −0.10491 (16) | 1.04586 (15) | 0.02688 (6) | 0.0662 (4) | |
O3 | 0.58398 (17) | 0.17601 (16) | 0.20847 (7) | 0.0769 (5) | |
O4 | 0.55754 (19) | 0.3486 (2) | 0.26809 (9) | 0.0993 (6) | |
C1 | 0.0382 (3) | 1.0920 (2) | 0.01362 (9) | 0.0637 (6) | |
C2 | −0.1101 (2) | 0.9179 (2) | 0.05082 (9) | 0.0590 (5) | |
H2A | −0.0683 | 0.8579 | 0.0218 | 0.071* | |
H2B | −0.2109 | 0.8931 | 0.0579 | 0.071* | |
C3 | −0.02477 (19) | 0.9113 (2) | 0.11020 (8) | 0.0479 (5) | |
C4 | −0.02656 (19) | 0.77660 (19) | 0.14203 (8) | 0.0476 (5) | |
H4 | 0.0091 | 0.7943 | 0.1831 | 0.057* | |
C5 | −0.1809 (2) | 0.7225 (2) | 0.15176 (11) | 0.0645 (6) | |
H5A | −0.2449 | 0.7907 | 0.1662 | 0.077* | |
H5B | −0.2194 | 0.6907 | 0.1136 | 0.077* | |
C6 | −0.1767 (2) | 0.6129 (2) | 0.19793 (11) | 0.0731 (7) | |
H6A | −0.1541 | 0.6483 | 0.2375 | 0.088* | |
H6B | −0.2727 | 0.5733 | 0.2002 | 0.088* | |
C7 | −0.0660 (2) | 0.5109 (2) | 0.18241 (9) | 0.0611 (6) | |
C8 | 0.0846 (2) | 0.56338 (19) | 0.16858 (8) | 0.0490 (5) | |
H8 | 0.1181 | 0.6069 | 0.2055 | 0.059* | |
C9 | 0.07770 (19) | 0.66999 (19) | 0.11787 (7) | 0.0452 (4) | |
C10 | 0.22974 (19) | 0.7287 (2) | 0.10976 (8) | 0.0531 (5) | |
H10A | 0.2686 | 0.7521 | 0.1491 | 0.064* | |
H10B | 0.2942 | 0.6643 | 0.0922 | 0.064* | |
C11 | 0.2277 (2) | 0.8482 (2) | 0.06911 (9) | 0.0576 (5) | |
H11A | 0.3263 | 0.8809 | 0.0642 | 0.069* | |
H11B | 0.1905 | 0.8252 | 0.0294 | 0.069* | |
C12 | 0.1322 (2) | 0.9515 (2) | 0.09682 (8) | 0.0517 (5) | |
H12 | 0.1760 | 0.9708 | 0.1363 | 0.062* | |
C13 | 0.1914 (2) | 0.4572 (2) | 0.15645 (9) | 0.0544 (5) | |
H13 | 0.1839 | 0.4137 | 0.1197 | 0.065* | |
C14 | 0.2960 (2) | 0.4206 (2) | 0.19415 (8) | 0.0517 (5) | |
H14 | 0.3107 | 0.4707 | 0.2286 | 0.062* | |
C15 | 0.38948 (19) | 0.3085 (2) | 0.18619 (8) | 0.0487 (5) | |
C16 | 0.3841 (2) | 0.2107 (2) | 0.14811 (9) | 0.0576 (5) | |
H16 | 0.3126 | 0.1997 | 0.1186 | 0.069* | |
C17 | 0.5067 (2) | 0.1209 (2) | 0.15851 (11) | 0.0720 (6) | |
H17A | 0.4713 | 0.0351 | 0.1684 | 0.086* | |
H17B | 0.5688 | 0.1154 | 0.1230 | 0.086* | |
C18 | 0.5145 (2) | 0.2856 (2) | 0.22602 (11) | 0.0626 (6) | |
C19 | 0.0950 (3) | 1.0332 (3) | −0.04483 (9) | 0.0836 (8) | |
H19A | 0.0983 | 0.9408 | −0.0409 | 0.125* | |
H19B | 0.1914 | 1.0655 | −0.0529 | 0.125* | |
H19C | 0.0311 | 1.0561 | −0.0776 | 0.125* | |
C20 | 0.0237 (3) | 1.2375 (3) | 0.00872 (13) | 0.0881 (8) | |
H20A | −0.0170 | 1.2711 | 0.0456 | 0.132* | |
H20B | −0.0393 | 1.2586 | −0.0246 | 0.132* | |
H20C | 0.1184 | 1.2750 | 0.0021 | 0.132* | |
C21 | −0.0916 (3) | 1.0115 (2) | 0.15365 (10) | 0.0698 (6) | |
H21A | −0.0770 | 1.0968 | 0.1376 | 0.105* | |
H21B | −0.0452 | 1.0049 | 0.1925 | 0.105* | |
H21C | −0.1944 | 0.9953 | 0.1579 | 0.105* | |
C22 | 0.0279 (2) | 0.6070 (2) | 0.05805 (8) | 0.0568 (5) | |
H22A | 0.0128 | 0.6729 | 0.0280 | 0.085* | |
H22B | −0.0617 | 0.5609 | 0.0646 | 0.085* | |
H22C | 0.1017 | 0.5480 | 0.0442 | 0.085* | |
C23 | −0.0983 (3) | 0.3865 (3) | 0.18327 (13) | 0.0845 (8) | |
H23A | −0.1920 | 0.3597 | 0.1937 | 0.101* | |
H23B | −0.0274 | 0.3256 | 0.1734 | 0.101* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0777 (9) | 0.0520 (9) | 0.0589 (7) | −0.0050 (8) | −0.0153 (7) | 0.0082 (8) |
O2 | 0.0710 (9) | 0.0627 (10) | 0.0650 (8) | 0.0142 (9) | −0.0138 (7) | 0.0073 (8) |
O3 | 0.0659 (9) | 0.0713 (11) | 0.0935 (10) | 0.0222 (9) | −0.0172 (8) | 0.0030 (10) |
O4 | 0.0944 (12) | 0.1037 (15) | 0.0998 (12) | 0.0255 (12) | −0.0441 (11) | −0.0213 (12) |
C1 | 0.0788 (14) | 0.0597 (15) | 0.0525 (10) | 0.0114 (13) | −0.0078 (10) | 0.0076 (11) |
C2 | 0.0595 (11) | 0.0560 (14) | 0.0615 (11) | 0.0092 (12) | −0.0137 (9) | 0.0027 (11) |
C3 | 0.0532 (10) | 0.0468 (12) | 0.0436 (8) | 0.0086 (10) | −0.0037 (8) | −0.0042 (9) |
C4 | 0.0488 (9) | 0.0484 (12) | 0.0457 (9) | 0.0070 (10) | −0.0015 (8) | −0.0042 (9) |
C5 | 0.0505 (10) | 0.0598 (15) | 0.0833 (14) | 0.0113 (11) | 0.0113 (10) | 0.0011 (13) |
C6 | 0.0611 (12) | 0.0641 (15) | 0.0941 (15) | 0.0032 (13) | 0.0236 (12) | 0.0094 (14) |
C7 | 0.0638 (12) | 0.0563 (14) | 0.0633 (12) | 0.0009 (12) | 0.0030 (10) | 0.0064 (11) |
C8 | 0.0545 (10) | 0.0456 (12) | 0.0471 (9) | 0.0081 (10) | −0.0043 (8) | −0.0008 (9) |
C9 | 0.0443 (9) | 0.0473 (12) | 0.0441 (8) | 0.0057 (9) | −0.0041 (7) | −0.0038 (9) |
C10 | 0.0453 (9) | 0.0591 (13) | 0.0548 (10) | 0.0071 (10) | −0.0037 (8) | 0.0009 (11) |
C11 | 0.0490 (10) | 0.0628 (14) | 0.0609 (10) | 0.0020 (11) | 0.0027 (9) | 0.0062 (11) |
C12 | 0.0628 (11) | 0.0475 (12) | 0.0447 (9) | 0.0001 (11) | −0.0118 (8) | 0.0012 (9) |
C13 | 0.0616 (11) | 0.0513 (13) | 0.0503 (9) | 0.0096 (11) | −0.0041 (9) | −0.0034 (10) |
C14 | 0.0535 (10) | 0.0529 (13) | 0.0487 (9) | 0.0029 (11) | −0.0013 (8) | 0.0000 (10) |
C15 | 0.0453 (9) | 0.0513 (12) | 0.0497 (9) | 0.0009 (10) | 0.0021 (8) | 0.0102 (10) |
C16 | 0.0562 (11) | 0.0555 (13) | 0.0611 (11) | 0.0043 (12) | −0.0025 (9) | 0.0074 (12) |
C17 | 0.0744 (13) | 0.0588 (14) | 0.0827 (14) | 0.0143 (13) | −0.0075 (12) | 0.0036 (14) |
C18 | 0.0552 (11) | 0.0613 (15) | 0.0712 (13) | 0.0067 (13) | −0.0104 (11) | 0.0072 (13) |
C19 | 0.1032 (18) | 0.0931 (19) | 0.0545 (11) | 0.0179 (18) | −0.0018 (12) | 0.0086 (13) |
C20 | 0.122 (2) | 0.0637 (16) | 0.0787 (15) | 0.0091 (18) | −0.0170 (15) | 0.0151 (14) |
C21 | 0.0923 (16) | 0.0533 (14) | 0.0637 (12) | 0.0194 (14) | 0.0070 (12) | −0.0063 (11) |
C22 | 0.0665 (12) | 0.0518 (13) | 0.0520 (10) | 0.0102 (12) | −0.0092 (9) | −0.0079 (10) |
C23 | 0.0786 (16) | 0.0621 (16) | 0.1129 (19) | −0.0042 (15) | 0.0097 (15) | 0.0039 (16) |
Geometric parameters (Å, º) top
O1—C1 | 1.430 (2) | C10—C11 | 1.527 (3) |
O1—C12 | 1.450 (2) | C10—H10A | 0.97 |
O2—C1 | 1.424 (3) | C10—H10B | 0.97 |
O2—C2 | 1.426 (3) | C11—C12 | 1.510 (3) |
O3—C18 | 1.356 (3) | C11—H11A | 0.97 |
O3—C17 | 1.428 (3) | C11—H11B | 0.97 |
O4—C18 | 1.201 (3) | C12—H12 | 0.98 |
C1—C20 | 1.515 (4) | C13—C14 | 1.323 (3) |
C1—C19 | 1.518 (3) | C13—H13 | 0.93 |
C2—C3 | 1.527 (2) | C14—C15 | 1.452 (3) |
C2—H2A | 0.97 | C14—H14 | 0.93 |
C2—H2B | 0.97 | C15—C16 | 1.316 (3) |
C3—C12 | 1.525 (3) | C15—C18 | 1.462 (3) |
C3—C21 | 1.539 (3) | C16—C17 | 1.475 (3) |
C3—C4 | 1.560 (3) | C16—H16 | 0.93 |
C4—C5 | 1.535 (3) | C17—H17A | 0.97 |
C4—C9 | 1.553 (3) | C17—H17B | 0.97 |
C4—H4 | 0.98 | C19—H19A | 0.96 |
C5—C6 | 1.525 (3) | C19—H19B | 0.96 |
C5—H5A | 0.97 | C19—H19C | 0.96 |
C5—H5B | 0.97 | C20—H20A | 0.96 |
C6—C7 | 1.502 (3) | C20—H20B | 0.96 |
C6—H6A | 0.97 | C20—H20C | 0.96 |
C6—H6B | 0.97 | C21—H21A | 0.96 |
C7—C23 | 1.321 (3) | C21—H21B | 0.96 |
C7—C8 | 1.513 (3) | C21—H21C | 0.96 |
C8—C13 | 1.495 (3) | C22—H22A | 0.96 |
C8—C9 | 1.572 (3) | C22—H22B | 0.96 |
C8—H8 | 0.98 | C22—H22C | 0.96 |
C9—C10 | 1.529 (3) | C23—H23A | 0.93 |
C9—C22 | 1.541 (2) | C23—H23B | 0.93 |
| | | |
C1—O1—C12 | 120.01 (16) | C12—C11—C10 | 110.01 (15) |
C1—O2—C2 | 114.69 (16) | C12—C11—H11A | 109.7 |
C18—O3—C17 | 108.78 (17) | C10—C11—H11A | 109.7 |
O2—C1—O1 | 111.56 (16) | C12—C11—H11B | 109.7 |
O2—C1—C20 | 105.5 (2) | C10—C11—H11B | 109.7 |
O1—C1—C20 | 104.5 (2) | H11A—C11—H11B | 108.2 |
O2—C1—C19 | 110.8 (2) | O1—C12—C11 | 113.06 (15) |
O1—C1—C19 | 112.48 (18) | O1—C12—C3 | 110.69 (16) |
C20—C1—C19 | 111.6 (2) | C11—C12—C3 | 115.50 (17) |
O2—C2—C3 | 110.03 (17) | O1—C12—H12 | 105.6 |
O2—C2—H2A | 109.7 | C11—C12—H12 | 105.6 |
C3—C2—H2A | 109.7 | C3—C12—H12 | 105.6 |
O2—C2—H2B | 109.7 | C14—C13—C8 | 124.81 (18) |
C3—C2—H2B | 109.7 | C14—C13—H13 | 117.6 |
H2A—C2—H2B | 108.2 | C8—C13—H13 | 117.6 |
C12—C3—C2 | 107.67 (15) | C13—C14—C15 | 125.37 (18) |
C12—C3—C21 | 108.16 (18) | C13—C14—H14 | 117.3 |
C2—C3—C21 | 107.53 (16) | C15—C14—H14 | 117.3 |
C12—C3—C4 | 109.91 (15) | C16—C15—C14 | 132.00 (17) |
C2—C3—C4 | 114.89 (16) | C16—C15—C18 | 106.77 (19) |
C21—C3—C4 | 108.47 (15) | C14—C15—C18 | 121.20 (19) |
C5—C4—C9 | 110.79 (17) | C15—C16—C17 | 110.86 (18) |
C5—C4—C3 | 113.46 (15) | C15—C16—H16 | 124.6 |
C9—C4—C3 | 118.24 (15) | C17—C16—H16 | 124.6 |
C5—C4—H4 | 104.2 | O3—C17—C16 | 104.22 (18) |
C9—C4—H4 | 104.2 | O3—C17—H17A | 110.9 |
C3—C4—H4 | 104.2 | C16—C17—H17A | 110.9 |
C6—C5—C4 | 109.97 (17) | O3—C17—H17B | 110.9 |
C6—C5—H5A | 109.7 | C16—C17—H17B | 110.9 |
C4—C5—H5A | 109.7 | H17A—C17—H17B | 108.9 |
C6—C5—H5B | 109.7 | O4—C18—O3 | 121.4 (2) |
C4—C5—H5B | 109.7 | O4—C18—C15 | 129.3 (2) |
H5A—C5—H5B | 108.2 | O3—C18—C15 | 109.3 (2) |
C7—C6—C5 | 112.75 (18) | C1—C19—H19A | 109.5 |
C7—C6—H6A | 109.0 | C1—C19—H19B | 109.5 |
C5—C6—H6A | 109.0 | H19A—C19—H19B | 109.5 |
C7—C6—H6B | 109.0 | C1—C19—H19C | 109.5 |
C5—C6—H6B | 109.0 | H19A—C19—H19C | 109.5 |
H6A—C6—H6B | 107.8 | H19B—C19—H19C | 109.5 |
C23—C7—C6 | 122.0 (2) | C1—C20—H20A | 109.5 |
C23—C7—C8 | 123.8 (2) | C1—C20—H20B | 109.5 |
C6—C7—C8 | 114.14 (19) | H20A—C20—H20B | 109.5 |
C13—C8—C7 | 111.64 (17) | C1—C20—H20C | 109.5 |
C13—C8—C9 | 114.47 (15) | H20A—C20—H20C | 109.5 |
C7—C8—C9 | 111.01 (14) | H20B—C20—H20C | 109.5 |
C13—C8—H8 | 106.4 | C3—C21—H21A | 109.5 |
C7—C8—H8 | 106.4 | C3—C21—H21B | 109.5 |
C9—C8—H8 | 106.4 | H21A—C21—H21B | 109.5 |
C10—C9—C22 | 109.67 (15) | C3—C21—H21C | 109.5 |
C10—C9—C4 | 108.52 (15) | H21A—C21—H21C | 109.5 |
C22—C9—C4 | 114.38 (15) | H21B—C21—H21C | 109.5 |
C10—C9—C8 | 108.97 (14) | C9—C22—H22A | 109.5 |
C22—C9—C8 | 108.97 (16) | C9—C22—H22B | 109.5 |
C4—C9—C8 | 106.16 (14) | H22A—C22—H22B | 109.5 |
C11—C10—C9 | 112.26 (15) | C9—C22—H22C | 109.5 |
C11—C10—H10A | 109.2 | H22A—C22—H22C | 109.5 |
C9—C10—H10A | 109.2 | H22B—C22—H22C | 109.5 |
C11—C10—H10B | 109.2 | C7—C23—H23A | 120.0 |
C9—C10—H10B | 109.2 | C7—C23—H23B | 120.0 |
H10A—C10—H10B | 107.9 | H23A—C23—H23B | 120.0 |
| | | |
C2—O2—C1—O1 | −49.4 (2) | C13—C8—C9—C22 | 61.9 (2) |
C2—O2—C1—C20 | −162.33 (17) | C7—C8—C9—C22 | −65.6 (2) |
C2—O2—C1—C19 | 76.8 (2) | C13—C8—C9—C4 | −174.45 (15) |
C12—O1—C1—O2 | 42.2 (2) | C7—C8—C9—C4 | 58.06 (19) |
C12—O1—C1—C20 | 155.79 (19) | C22—C9—C10—C11 | 70.4 (2) |
C12—O1—C1—C19 | −83.0 (2) | C4—C9—C10—C11 | −55.19 (19) |
C1—O2—C2—C3 | 60.4 (2) | C8—C9—C10—C11 | −170.38 (15) |
O2—C2—C3—C12 | −59.1 (2) | C9—C10—C11—C12 | 60.9 (2) |
O2—C2—C3—C21 | 57.3 (2) | C1—O1—C12—C11 | 86.7 (2) |
O2—C2—C3—C4 | 178.12 (15) | C1—O1—C12—C3 | −44.6 (2) |
C12—C3—C4—C5 | −174.50 (17) | C10—C11—C12—O1 | 174.73 (15) |
C2—C3—C4—C5 | −52.9 (2) | C10—C11—C12—C3 | −56.3 (2) |
C21—C3—C4—C5 | 67.4 (2) | C2—C3—C12—O1 | 50.2 (2) |
C12—C3—C4—C9 | −42.3 (2) | C21—C3—C12—O1 | −65.74 (18) |
C2—C3—C4—C9 | 79.3 (2) | C4—C3—C12—O1 | 176.00 (13) |
C21—C3—C4—C9 | −160.32 (16) | C2—C3—C12—C11 | −79.9 (2) |
C9—C4—C5—C6 | 60.3 (2) | C21—C3—C12—C11 | 164.17 (17) |
C3—C4—C5—C6 | −163.94 (16) | C4—C3—C12—C11 | 45.9 (2) |
C4—C5—C6—C7 | −52.4 (3) | C7—C8—C13—C14 | −106.7 (2) |
C5—C6—C7—C23 | −132.1 (3) | C9—C8—C13—C14 | 126.2 (2) |
C5—C6—C7—C8 | 50.4 (3) | C8—C13—C14—C15 | 172.48 (18) |
C23—C7—C8—C13 | −0.3 (3) | C13—C14—C15—C16 | −10.6 (3) |
C6—C7—C8—C13 | 177.24 (17) | C13—C14—C15—C18 | 171.7 (2) |
C23—C7—C8—C9 | 128.7 (2) | C14—C15—C16—C17 | 179.8 (2) |
C6—C7—C8—C9 | −53.7 (2) | C18—C15—C16—C17 | −2.3 (2) |
C5—C4—C9—C10 | −179.34 (16) | C18—O3—C17—C16 | 0.4 (2) |
C3—C4—C9—C10 | 47.3 (2) | C15—C16—C17—O3 | 1.2 (2) |
C5—C4—C9—C22 | 57.9 (2) | C17—O3—C18—O4 | 178.8 (2) |
C3—C4—C9—C22 | −75.5 (2) | C17—O3—C18—C15 | −1.7 (2) |
C5—C4—C9—C8 | −62.33 (19) | C16—C15—C18—O4 | −178.1 (3) |
C3—C4—C9—C8 | 164.26 (14) | C14—C15—C18—O4 | 0.1 (3) |
C13—C8—C9—C10 | −57.7 (2) | C16—C15—C18—O3 | 2.5 (2) |
C7—C8—C9—C10 | 174.76 (17) | C14—C15—C18—O3 | −179.28 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16···O1i | 0.93 | 2.42 | 3.273 (2) | 153 |
C17—H17A···O4ii | 0.97 | 2.40 | 3.302 (3) | 155 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, y−1/2, −z+1/2. |