Molecules in the title crystal structure, C
20H
24O
4, are linked into chains of
R44(8) rings along [010] and these chains are linked into sheets
via weak C—H
π(arene) interactions. These sheets are, in turn, linked
via weak C—H
π(arene) and C—H
O interactions into a three-dimensional network. The ethyl substituent is disordered over two sites with refined occupancies of 0.700 (5) and 0.300 (5).
Supporting information
CCDC reference: 608449
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.057
- wR factor = 0.118
- Data-to-parameter ratio = 17.1
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT432_ALERT_2_A Short Inter X...Y Contact C13B .. C13B .. 2.51 Ang.
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc.
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.33 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.76 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O1
PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13A .. CG1 .. 3.24 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13F .. CG1 .. 2.95 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14B .. CG1 .. 2.95 Ang.
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
3 ALERT type 3 Indicator that the structure quality may be low
3 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: ...
This is a colaboration between people belonging to different institutions:
- The synthesis and NMR ( 3 people )
- Diffraction ( 2 people )
- Writting of the paper (1 person)
|
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: SMART-NT (Bruker, 2001); cell refinement: SAINT-NT (Bruker, 2000); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-PC (Sheldrick, 1994); software used to prepare material for publication: PLATON (Spek, 2003) and Mercury (Bruno et al., 2002).
1-Ethyl-3-(4-hydroxy-3-methoxyphenyl)-6-methoxy-2-methylindan-5-ol
top
Crystal data top
C20H24O4 | Z = 2 |
Mr = 328.39 | F(000) = 352 |
Triclinic, P1 | Dx = 1.211 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.5124 (10) Å | Cell parameters from 6723 reflections |
b = 10.7915 (16) Å | θ = 2.0–28.1° |
c = 14.147 (2) Å | µ = 0.08 mm−1 |
α = 69.514 (2)° | T = 298 K |
β = 76.847 (3)° | Needle, colorless |
γ = 79.238 (3)° | 0.39 × 0.15 × 0.10 mm |
V = 900.7 (2) Å3 | |
Data collection top
Bruker SMART-NT CCD area-detector diffractometer | Rint = 0.045 |
φ and ω scans | θmax = 28.1°, θmin = 2.0° |
6723 measured reflections | h = −8→8 |
3926 independent reflections | k = −13→14 |
1834 reflections with I > 2σ(I) | l = −17→17 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 0.88 | w = 1/[σ2(Fo2) + (0.0333P)2] where P = (Fo2 + 2Fc2)/3 |
3926 reflections | (Δ/σ)max < 0.001 |
230 parameters | Δρmax = 0.19 e Å−3 |
18 restraints | Δρmin = −0.16 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs 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 | Occ. (<1) |
O1 | 0.3937 (3) | 1.08644 (16) | 0.31013 (14) | 0.0751 (8) | |
O2 | 0.0407 (2) | 0.97138 (14) | 0.36783 (12) | 0.0603 (7) | |
O3 | 0.1936 (3) | 0.31070 (17) | 0.51064 (13) | 0.0753 (8) | |
O4 | −0.0264 (2) | 0.20306 (15) | 0.42884 (12) | 0.0633 (7) | |
C1 | 0.5755 (5) | 1.1516 (3) | 0.2823 (3) | 0.135 (2) | |
C2 | 0.3992 (4) | 0.9831 (2) | 0.27496 (19) | 0.0501 (9) | |
C3 | 0.2102 (4) | 0.9251 (2) | 0.30602 (17) | 0.0470 (9) | |
C4 | 0.1906 (3) | 0.8196 (2) | 0.27752 (17) | 0.0470 (9) | |
C5 | 0.3608 (3) | 0.7706 (2) | 0.21675 (16) | 0.0405 (8) | |
C6 | 0.3757 (3) | 0.6582 (2) | 0.17493 (16) | 0.0447 (8) | |
C7 | 0.6188 (3) | 0.6248 (2) | 0.14741 (17) | 0.0463 (9) | |
C8 | 0.6805 (4) | 0.5488 (3) | 0.07072 (19) | 0.0712 (11) | |
C9 | 0.5676 (4) | 0.9339 (2) | 0.21480 (18) | 0.0521 (9) | |
C10 | 0.5486 (3) | 0.8264 (2) | 0.18617 (16) | 0.0425 (8) | |
C11 | 0.7100 (3) | 0.7582 (2) | 0.11956 (17) | 0.0490 (9) | |
C12 | 0.7373 (4) | 0.8434 (3) | 0.00601 (19) | 0.0732 (11) | |
C13A | 0.9397 (6) | 0.8166 (5) | −0.0608 (3) | 0.0905 (19) | 0.700 (5) |
C14 | 0.3252 (5) | 0.3572 (3) | 0.5549 (2) | 0.1032 (16) | |
C15 | 0.1856 (4) | 0.3735 (2) | 0.40886 (18) | 0.0487 (9) | |
C16 | 0.0675 (3) | 0.3154 (2) | 0.3696 (2) | 0.0475 (9) | |
C17 | 0.0474 (4) | 0.3689 (2) | 0.2690 (2) | 0.0544 (10) | |
C18 | 0.1447 (3) | 0.4805 (2) | 0.20653 (19) | 0.0509 (9) | |
C19 | 0.2628 (3) | 0.5401 (2) | 0.24361 (17) | 0.0405 (8) | |
C20 | 0.2806 (4) | 0.4846 (2) | 0.34687 (18) | 0.0504 (9) | |
C13B | 0.8665 (16) | 0.9462 (11) | −0.0193 (7) | 0.098 (5) | 0.300 (5) |
H1A | 0.68870 | 1.09160 | 0.31300 | 0.2030* | |
H1B | 0.54570 | 1.22760 | 0.30570 | 0.2030* | |
H2 | 0.07000 | 1.03580 | 0.37800 | 0.0900* | |
H4 | −0.00010 | 0.17980 | 0.48700 | 0.0950* | |
H4A | 0.06430 | 0.78130 | 0.29880 | 0.0560* | |
H6 | 0.31840 | 0.69390 | 0.11100 | 0.0540* | |
H7 | 0.66700 | 0.56580 | 0.21070 | 0.0560* | |
H8A | 0.63780 | 0.60390 | 0.00690 | 0.1070* | |
H1C | 0.61680 | 1.18020 | 0.20900 | 0.2030* | |
H8C | 0.83160 | 0.52520 | 0.05980 | 0.1070* | |
H9 | 0.69380 | 0.97240 | 0.19330 | 0.0630* | |
H11 | 0.84700 | 0.74020 | 0.14230 | 0.0590* | |
H12A | 0.62210 | 0.83200 | −0.02220 | 0.0880* | 0.700 (5) |
H12B | 0.72120 | 0.93610 | 0.00220 | 0.0880* | 0.700 (5) |
H13A | 0.94310 | 0.88080 | −0.12810 | 0.1360* | 0.700 (5) |
H13B | 0.95050 | 0.72870 | −0.06510 | 0.1360* | 0.700 (5) |
H13C | 1.05660 | 0.82280 | −0.03240 | 0.1360* | 0.700 (5) |
H14A | 0.46860 | 0.35130 | 0.51870 | 0.1540* | |
H14B | 0.32050 | 0.30360 | 0.62560 | 0.1540* | |
H14C | 0.27580 | 0.44830 | 0.55060 | 0.1540* | |
H17 | −0.03200 | 0.33040 | 0.24220 | 0.0650* | |
H18 | 0.12970 | 0.51570 | 0.13800 | 0.0610* | |
H20 | 0.35820 | 0.52360 | 0.37420 | 0.0600* | |
H8B | 0.61100 | 0.46950 | 0.09700 | 0.1070* | |
H12C | 0.79950 | 0.78610 | −0.03540 | 0.0880* | 0.300 (5) |
H12D | 0.59850 | 0.88270 | −0.01110 | 0.0880* | 0.300 (5) |
H13D | 0.99670 | 0.90990 | 0.00640 | 0.1470* | 0.300 (5) |
H13E | 0.79310 | 1.01280 | 0.01090 | 0.1470* | 0.300 (5) |
H13F | 0.89740 | 0.98580 | −0.09250 | 0.1470* | 0.300 (5) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0574 (12) | 0.0603 (12) | 0.1231 (17) | −0.0178 (9) | −0.0002 (11) | −0.0528 (12) |
O2 | 0.0583 (11) | 0.0504 (11) | 0.0767 (13) | −0.0108 (8) | 0.0040 (10) | −0.0338 (10) |
O3 | 0.1080 (15) | 0.0730 (13) | 0.0515 (12) | −0.0482 (11) | −0.0232 (11) | −0.0034 (10) |
O4 | 0.0733 (12) | 0.0534 (11) | 0.0697 (12) | −0.0260 (9) | −0.0077 (9) | −0.0214 (10) |
C1 | 0.069 (2) | 0.124 (3) | 0.263 (5) | −0.025 (2) | −0.007 (3) | −0.131 (3) |
C2 | 0.0488 (16) | 0.0356 (14) | 0.0686 (18) | −0.0070 (12) | −0.0082 (14) | −0.0202 (13) |
C3 | 0.0471 (15) | 0.0387 (15) | 0.0519 (16) | −0.0052 (12) | −0.0025 (13) | −0.0142 (12) |
C4 | 0.0445 (15) | 0.0424 (15) | 0.0539 (16) | −0.0124 (12) | −0.0043 (12) | −0.0143 (13) |
C5 | 0.0423 (14) | 0.0387 (14) | 0.0377 (14) | −0.0058 (11) | −0.0074 (11) | −0.0082 (11) |
C6 | 0.0497 (15) | 0.0454 (15) | 0.0400 (14) | −0.0066 (12) | −0.0087 (12) | −0.0139 (12) |
C7 | 0.0479 (15) | 0.0508 (15) | 0.0434 (15) | −0.0012 (12) | −0.0093 (12) | −0.0206 (12) |
C8 | 0.0591 (17) | 0.091 (2) | 0.077 (2) | −0.0074 (15) | −0.0053 (15) | −0.0484 (18) |
C9 | 0.0452 (15) | 0.0418 (15) | 0.0654 (18) | −0.0120 (12) | −0.0062 (13) | −0.0111 (14) |
C10 | 0.0457 (14) | 0.0373 (14) | 0.0397 (14) | −0.0040 (12) | −0.0085 (11) | −0.0062 (11) |
C11 | 0.0435 (14) | 0.0526 (16) | 0.0482 (16) | −0.0061 (12) | −0.0070 (12) | −0.0134 (13) |
C12 | 0.0698 (19) | 0.078 (2) | 0.0560 (19) | −0.0098 (17) | 0.0032 (15) | −0.0104 (16) |
C13A | 0.073 (3) | 0.100 (4) | 0.064 (3) | 0.004 (3) | 0.016 (2) | −0.009 (3) |
C14 | 0.146 (3) | 0.112 (3) | 0.062 (2) | −0.067 (2) | −0.049 (2) | 0.0048 (18) |
C15 | 0.0596 (16) | 0.0458 (15) | 0.0431 (16) | −0.0144 (13) | −0.0110 (13) | −0.0117 (13) |
C16 | 0.0476 (15) | 0.0405 (15) | 0.0596 (18) | −0.0122 (12) | −0.0039 (13) | −0.0224 (14) |
C17 | 0.0575 (17) | 0.0553 (17) | 0.0643 (19) | −0.0132 (13) | −0.0183 (14) | −0.0281 (15) |
C18 | 0.0559 (16) | 0.0519 (16) | 0.0521 (16) | −0.0061 (13) | −0.0145 (13) | −0.0225 (14) |
C19 | 0.0429 (14) | 0.0407 (14) | 0.0413 (14) | −0.0031 (11) | −0.0076 (11) | −0.0180 (12) |
C20 | 0.0597 (16) | 0.0511 (16) | 0.0503 (16) | −0.0167 (13) | −0.0143 (13) | −0.0204 (13) |
C13B | 0.109 (9) | 0.083 (9) | 0.074 (8) | −0.047 (7) | −0.002 (6) | 0.018 (6) |
Geometric parameters (Å, º) top
O1—C1 | 1.399 (4) | C19—C20 | 1.395 (3) |
O1—C2 | 1.363 (3) | C1—H1A | 0.9600 |
O2—C3 | 1.376 (3) | C1—H1B | 0.9600 |
O3—C14 | 1.415 (4) | C1—H1C | 0.9600 |
O3—C15 | 1.369 (3) | C4—H4A | 0.9300 |
O4—C16 | 1.371 (3) | C6—H6 | 0.9800 |
O2—H2 | 0.8200 | C7—H7 | 0.9800 |
O4—H4 | 0.8200 | C8—H8A | 0.9600 |
C2—C9 | 1.372 (4) | C8—H8B | 0.9600 |
C2—C3 | 1.396 (4) | C8—H8C | 0.9600 |
C3—C4 | 1.369 (3) | C9—H9 | 0.9300 |
C4—C5 | 1.383 (3) | C11—H11 | 0.9800 |
C5—C10 | 1.378 (3) | C12—H12A | 0.9700 |
C5—C6 | 1.504 (3) | C12—H12B | 0.9700 |
C6—C19 | 1.506 (3) | C12—H12C | 0.9700 |
C6—C7 | 1.547 (3) | C12—H12D | 0.9700 |
C7—C11 | 1.548 (3) | C13A—H13A | 0.9600 |
C7—C8 | 1.521 (4) | C13A—H13B | 0.9600 |
C9—C10 | 1.389 (3) | C13A—H13C | 0.9600 |
C10—C11 | 1.510 (3) | C13B—H13E | 0.9600 |
C11—C12 | 1.535 (3) | C13B—H13F | 0.9600 |
C12—C13A | 1.482 (5) | C13B—H13D | 0.9600 |
C12—C13B | 1.414 (12) | C14—H14C | 0.9600 |
C15—C20 | 1.372 (3) | C14—H14A | 0.9600 |
C15—C16 | 1.383 (3) | C14—H14B | 0.9600 |
C16—C17 | 1.363 (4) | C17—H17 | 0.9300 |
C17—C18 | 1.385 (3) | C18—H18 | 0.9300 |
C18—C19 | 1.373 (3) | C20—H20 | 0.9300 |
| | | |
O1···O2 | 2.645 (2) | H4···O3 | 2.2100 |
O1···O4i | 3.161 (2) | H4···C3ii | 2.8600 |
O1···C16i | 3.163 (3) | H4···H2iii | 2.4700 |
O1···C17i | 3.392 (3) | H4···O2ii | 2.1300 |
O2···O1 | 2.645 (2) | H4···H2ii | 2.4800 |
O2···O4i | 2.849 (2) | H4A···O3ii | 2.7900 |
O2···O4ii | 2.825 (2) | H4A···C19 | 2.9600 |
O3···O4 | 2.657 (2) | H6···H8A | 2.5100 |
O4···O2iii | 2.849 (2) | H6···H18 | 2.3500 |
O4···O3 | 2.657 (2) | H7···C17viii | 3.0100 |
O4···O1iii | 3.161 (2) | H7···C18viii | 3.0700 |
O4···O2ii | 2.825 (2) | H7···C20 | 2.8700 |
O1···H2 | 2.1900 | H8A···H6 | 2.5100 |
O2···H4ii | 2.1300 | H8A···H12A | 2.3400 |
O2···H1Aiv | 2.5600 | H8A···C12 | 2.7700 |
O3···H4Aii | 2.7900 | H8A···C13A | 3.0600 |
O3···H4 | 2.2100 | H8A···H13B | 2.4700 |
O4···H2iii | 2.1100 | H8A···H12C | 2.2400 |
C4···C20 | 3.371 (3) | H8B···C18 | 3.0800 |
C8···C13A | 3.360 (6) | H8B···C19 | 2.8900 |
C9···C13B | 3.410 (10) | H8C···H18viii | 2.4100 |
C13A···C8 | 3.360 (6) | H8C···C18viii | 3.0900 |
C13B···C13Bv | 2.510 (16) | H8C···H13B | 2.4200 |
C13B···C9 | 3.410 (10) | H8C···H8Cix | 2.5500 |
C16···O1iii | 3.163 (3) | H9···C1 | 2.5700 |
C17···O1iii | 3.392 (3) | H9···H1A | 2.4500 |
C20···C4 | 3.371 (3) | H9···H13E | 2.4100 |
C1···H9 | 2.5700 | H9···C13B | 3.0500 |
C3···H4ii | 2.8600 | H9···H1C | 2.2800 |
C3···H13Avi | 2.9000 | H11···H13D | 2.3100 |
C3···H13Fvi | 3.0400 | H11···H13C | 2.4800 |
C4···H20 | 3.1000 | H11···C18viii | 3.0700 |
C4···H13Fvi | 2.8200 | H12A···H8A | 2.3400 |
C5···H13Fvi | 3.0500 | H12A···C6 | 3.0500 |
C5···H20 | 2.8100 | H12A···C8 | 2.8600 |
C6···H12A | 3.0500 | H12B···C9 | 2.9400 |
C8···H12A | 2.8600 | H12C···C8 | 2.6300 |
C8···H13B | 2.7700 | H12C···H8A | 2.2400 |
C8···H12C | 2.6300 | H12D···H13Evi | 2.5900 |
C9···H13E | 2.8300 | H13A···C3vi | 2.9000 |
C9···H14Bvii | 2.8600 | H13B···H8A | 2.4700 |
C9···H12B | 2.9400 | H13B···C8 | 2.7700 |
C9···H1A | 2.8500 | H13B···H8C | 2.4200 |
C9···H1C | 2.7100 | H13C···H11 | 2.4800 |
C10···H14Bvii | 2.7900 | H13D···C13Bv | 2.0100 |
C10···H13E | 2.9400 | H13D···H13Dv | 1.9000 |
C12···H8A | 2.7700 | H13D···H13Fv | 2.2000 |
C13A···H8A | 3.0600 | H13D···H13Ev | 1.6600 |
C13B···H13Fv | 2.7800 | H13D···H11 | 2.3100 |
C13B···H13Ev | 2.3800 | H13E···C9 | 2.8300 |
C13B···H9 | 3.0500 | H13E···H12Dvi | 2.5900 |
C13B···H13Dv | 2.0100 | H13E···H13Dv | 1.6600 |
C14···H20 | 2.5500 | H13E···H13Fv | 2.5500 |
C15···H1Biii | 2.9600 | H13E···C10 | 2.9400 |
C16···H2iii | 2.9700 | H13E···H9 | 2.4100 |
C17···H7iv | 3.0100 | H13E···C13Bv | 2.3800 |
C18···H11iv | 3.0700 | H13F···C3vi | 3.0400 |
C18···H7iv | 3.0700 | H13F···C4vi | 2.8200 |
C18···H8B | 3.0800 | H13F···C5vi | 3.0500 |
C18···H8Civ | 3.0900 | H13F···H13Ev | 2.5500 |
C19···H8B | 2.8900 | H13F···C13Bv | 2.7800 |
C19···H4A | 2.9600 | H13F···H13Dv | 2.2000 |
C20···H7 | 2.8700 | H14A···C20 | 2.7800 |
C20···H14A | 2.7800 | H14A···H20 | 2.3800 |
C20···H14C | 2.7600 | H14B···C9vii | 2.8600 |
H1A···C9 | 2.8500 | H14B···C10vii | 2.7900 |
H1A···O2viii | 2.5600 | H14C···C20 | 2.7600 |
H1A···H9 | 2.4500 | H14C···H20 | 2.3000 |
H1B···C15i | 2.9600 | H18···H8Civ | 2.4100 |
H1C···H9 | 2.2800 | H18···H6 | 2.3500 |
H1C···C9 | 2.7100 | H20···C14 | 2.5500 |
H2···H4i | 2.4700 | H20···H14A | 2.3800 |
H2···H4ii | 2.4800 | H20···H14C | 2.3000 |
H2···O4i | 2.1100 | H20···C5 | 2.8100 |
H2···C16i | 2.9700 | H20···C4 | 3.1000 |
H2···O1 | 2.1900 | | |
| | | |
C1—O1—C2 | 118.0 (2) | C7—C6—H6 | 108.00 |
C14—O3—C15 | 117.5 (2) | C19—C6—H6 | 108.00 |
C3—O2—H2 | 109.00 | C6—C7—H7 | 107.00 |
C16—O4—H4 | 109.00 | C8—C7—H7 | 107.00 |
O1—C2—C9 | 126.7 (2) | C11—C7—H7 | 107.00 |
O1—C2—C3 | 113.8 (2) | C7—C8—H8A | 109.00 |
O3—C15—C20 | 126.0 (2) | C7—C8—H8B | 109.00 |
O3—C15—C16 | 113.9 (2) | C7—C8—H8C | 109.00 |
C3—C2—C9 | 119.6 (2) | H8A—C8—H8B | 109.00 |
C2—C3—C4 | 120.9 (2) | H8A—C8—H8C | 109.00 |
O2—C3—C2 | 120.5 (2) | H8B—C8—H8C | 110.00 |
O2—C3—C4 | 118.6 (2) | C2—C9—H9 | 120.00 |
C3—C4—C5 | 119.2 (2) | C10—C9—H9 | 120.00 |
C6—C5—C10 | 110.84 (18) | C7—C11—H11 | 109.00 |
C4—C5—C6 | 128.78 (19) | C10—C11—H11 | 109.00 |
C4—C5—C10 | 120.4 (2) | C12—C11—H11 | 109.00 |
C5—C6—C19 | 116.62 (18) | C11—C12—H12A | 108.00 |
C5—C6—C7 | 101.76 (17) | C11—C12—H12B | 108.00 |
C7—C6—C19 | 113.91 (18) | C11—C12—H12C | 109.00 |
C6—C7—C11 | 104.99 (17) | C11—C12—H12D | 109.00 |
C6—C7—C8 | 112.68 (19) | C13A—C12—H12A | 108.00 |
C8—C7—C11 | 118.24 (19) | C13A—C12—H12B | 108.00 |
C2—C9—C10 | 119.7 (2) | H12A—C12—H12B | 107.00 |
C5—C10—C11 | 111.05 (19) | C13B—C12—H12C | 109.00 |
C5—C10—C9 | 120.2 (2) | C13B—C12—H12D | 109.00 |
C9—C10—C11 | 128.7 (2) | H12C—C12—H12D | 108.00 |
C7—C11—C12 | 116.0 (2) | C12—C13A—H13A | 110.00 |
C7—C11—C10 | 101.30 (17) | C12—C13A—H13B | 109.00 |
C10—C11—C12 | 112.0 (2) | C12—C13A—H13C | 109.00 |
C11—C12—C13A | 117.3 (3) | H13A—C13A—H13B | 109.00 |
C11—C12—C13B | 113.5 (4) | H13A—C13A—H13C | 110.00 |
C16—C15—C20 | 120.1 (2) | H13B—C13A—H13C | 109.00 |
O4—C16—C17 | 118.9 (2) | H13D—C13B—H13E | 109.00 |
O4—C16—C15 | 121.6 (2) | H13D—C13B—H13F | 109.00 |
C15—C16—C17 | 119.5 (2) | H13E—C13B—H13F | 109.00 |
C16—C17—C18 | 120.3 (2) | C12—C13B—H13E | 109.00 |
C17—C18—C19 | 121.4 (2) | C12—C13B—H13F | 109.00 |
C6—C19—C18 | 121.5 (2) | C12—C13B—H13D | 110.00 |
C6—C19—C20 | 120.9 (2) | H14A—C14—H14B | 109.00 |
C18—C19—C20 | 117.6 (2) | H14A—C14—H14C | 109.00 |
C15—C20—C19 | 121.2 (2) | O3—C14—H14A | 110.00 |
O1—C1—H1A | 109.00 | O3—C14—H14B | 109.00 |
O1—C1—H1B | 109.00 | O3—C14—H14C | 109.00 |
O1—C1—H1C | 109.00 | H14B—C14—H14C | 109.00 |
H1A—C1—H1B | 110.00 | C18—C17—H17 | 120.00 |
H1A—C1—H1C | 109.00 | C16—C17—H17 | 120.00 |
H1B—C1—H1C | 110.00 | C17—C18—H18 | 119.00 |
C3—C4—H4A | 120.00 | C19—C18—H18 | 119.00 |
C5—C4—H4A | 120.00 | C19—C20—H20 | 119.00 |
C5—C6—H6 | 108.00 | C15—C20—H20 | 119.00 |
| | | |
C1—O1—C2—C3 | −179.5 (2) | C7—C6—C19—C20 | 72.5 (3) |
C1—O1—C2—C9 | 0.7 (4) | C19—C6—C7—C8 | 73.6 (2) |
C14—O3—C15—C16 | 175.0 (2) | C6—C7—C11—C10 | 30.2 (2) |
C14—O3—C15—C20 | −5.4 (4) | C8—C7—C11—C12 | 35.3 (3) |
O1—C2—C3—C4 | −179.6 (2) | C8—C7—C11—C10 | 156.8 (2) |
O1—C2—C9—C10 | 179.3 (2) | C6—C7—C11—C12 | −91.4 (2) |
C9—C2—C3—O2 | 178.9 (2) | C2—C9—C10—C5 | 0.9 (3) |
C9—C2—C3—C4 | 0.2 (4) | C2—C9—C10—C11 | 178.8 (2) |
O1—C2—C3—O2 | −0.9 (3) | C5—C10—C11—C7 | −19.4 (2) |
C3—C2—C9—C10 | −0.5 (4) | C5—C10—C11—C12 | 104.9 (2) |
C2—C3—C4—C5 | −0.3 (3) | C9—C10—C11—C7 | 162.5 (2) |
O2—C3—C4—C5 | −179.0 (2) | C9—C10—C11—C12 | −73.2 (3) |
C3—C4—C5—C6 | −179.0 (2) | C10—C11—C12—C13A | 157.0 (3) |
C3—C4—C5—C10 | 0.7 (3) | C7—C11—C12—C13A | −87.4 (3) |
C4—C5—C6—C19 | −37.0 (3) | O3—C15—C16—C17 | 180.0 (2) |
C4—C5—C6—C7 | −161.5 (2) | O3—C15—C16—O4 | −1.6 (3) |
C4—C5—C10—C11 | −179.26 (19) | O3—C15—C20—C19 | 179.7 (2) |
C6—C5—C10—C9 | 178.7 (2) | C20—C15—C16—O4 | 178.8 (2) |
C6—C5—C10—C11 | 0.5 (2) | C20—C15—C16—C17 | 0.4 (4) |
C10—C5—C6—C19 | 143.32 (19) | C16—C15—C20—C19 | −0.8 (4) |
C4—C5—C10—C9 | −1.0 (3) | C15—C16—C17—C18 | 0.1 (4) |
C10—C5—C6—C7 | 18.7 (2) | O4—C16—C17—C18 | −178.4 (2) |
C5—C6—C7—C8 | −160.05 (19) | C16—C17—C18—C19 | −0.1 (4) |
C5—C6—C7—C11 | −30.1 (2) | C17—C18—C19—C6 | 177.6 (2) |
C19—C6—C7—C11 | −156.42 (18) | C17—C18—C19—C20 | −0.3 (3) |
C5—C6—C19—C18 | 136.5 (2) | C6—C19—C20—C15 | −177.2 (2) |
C5—C6—C19—C20 | −45.6 (3) | C18—C19—C20—C15 | 0.8 (3) |
C7—C6—C19—C18 | −105.3 (2) | | |
Symmetry codes: (i) x, y+1, z; (ii) −x, −y+1, −z+1; (iii) x, y−1, z; (iv) x−1, y, z; (v) −x+2, −y+2, −z; (vi) −x+1, −y+2, −z; (vii) −x+1, −y+1, −z+1; (viii) x+1, y, z; (ix) −x+2, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1 | 0.82 | 2.19 | 2.645 (2) | 115 |
O2—H2···O4i | 0.82 | 2.11 | 2.849 (2) | 150 |
O4—H4···O3 | 0.82 | 2.21 | 2.657 (2) | 114 |
O4—H4···O2ii | 0.82 | 2.13 | 2.825 (2) | 143 |
C1—H1A···O2viii | 0.96 | 2.56 | 3.499 (4) | 167 |
C13A—H13A···Cg1vi | 0.96 | 3.24 | 3.999 (5) | 137 |
C13B—H13F···Cg1vi | 0.96 | 2.95 | 3.663 (10) | 132 |
C14—H14B···Cg1vii | 0.96 | 2.95 | 3.697 (3) | 137 |
Symmetry codes: (i) x, y+1, z; (ii) −x, −y+1, −z+1; (vi) −x+1, −y+2, −z; (vii) −x+1, −y+1, −z+1; (viii) x+1, y, z. |