organic compounds
(E)-2,2′-[3-(4-Fluorophenyl)prop-2-ene-1,1-diyl]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one)
aAdvanced Analysis Center, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea, bCenter for Neuro-Medicine, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea, and cCorporated R&D Center, Duksan Hi-Metal Co. Ltd, Cheonan-si, 331-821, Republic of Korea
*Correspondence e-mail: j9601@kist.re.kr
In the title compound, C25H29FO4, each cyclohexenone ring has an with the dimethyl-substituted atom as the flap. The hydroxy and carbonyl groups form two intramolecular O—H⋯O hydrogen bonds, as is typical for xanthene derivatives. In the crystal, very weak C—H⋯O hydrogen bonds link molecules into dimers.
Related literature
For the crystal structures of related xanthenes derivatives, see: Cha et al. (2011, 2012).
Experimental
Crystal data
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Refinement
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Data collection: RAPID-AUTO (Rigaku, 2006); cell RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: Il Milione (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure.
Supporting information
10.1107/S1600536813004364/cv5387sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813004364/cv5387Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813004364/cv5387Isup3.cml
To solution of 5,5-Dimethyl-1,3-cyclohexanedione (4.61 mmol), 4-fluorocinnamaldehyde(1.84 mmol) and 4 Å MS was added catalytic amounts of L-proline in under nitrogen atmosphere. The anhydrous ethyl acetate (2 ml) was added to a reaction mixture and the solution was stirred at room temperature for 10 h. The progress of reaction was monitored by TLC. After completion of reaction, the reaction mixture was filtered through pad of celite to remove MS and evaporation of the solvent afforded a mixture. The mixture was purified by flash
to afford the title compound as a colorless solid in yield 82%. Recrystallization from ethanol gave crystals suitable for X-ray analysis.All hydrogen atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.97 Å and Uiso(H) = 1.2 or 1.5 Ueq(C).
Data collection: RAPID-AUTO (Rigaku, 2006); cell
RAPID-AUTO (Rigaku, 2006); data reduction: RAPID-AUTO (Rigaku, 2006); program(s) used to solve structure: Il Milione (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).Fig. 1. The molecular structure of (I) showing the atomic numbering and 50% probability displacement ellipsoid. |
C25H29FO4 | F(000) = 1760.00 |
Mr = 412.50 | Dx = 1.235 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -C 2yc | Cell parameters from 14685 reflections |
a = 26.1146 (13) Å | θ = 3.2–27.5° |
b = 9.6961 (4) Å | µ = 0.09 mm−1 |
c = 20.5638 (9) Å | T = 296 K |
β = 121.5921 (15)° | Block, colourless |
V = 4435.3 (4) Å3 | 0.30 × 0.20 × 0.10 mm |
Z = 8 |
Rigaku R-AXIS RAPID diffractometer | 3370 reflections with F2 > 2σ(F2) |
Detector resolution: 10.000 pixels mm-1 | Rint = 0.026 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995) | h = −33→33 |
Tmin = 0.771, Tmax = 0.991 | k = −10→12 |
21193 measured reflections | l = −26→26 |
5070 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0853P)2 + 0.9138P] where P = (Fo2 + 2Fc2)/3 |
5070 reflections | (Δ/σ)max < 0.001 |
281 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Primary atom site location: structure-invariant direct methods |
C25H29FO4 | V = 4435.3 (4) Å3 |
Mr = 412.50 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 26.1146 (13) Å | µ = 0.09 mm−1 |
b = 9.6961 (4) Å | T = 296 K |
c = 20.5638 (9) Å | 0.30 × 0.20 × 0.10 mm |
β = 121.5921 (15)° |
Rigaku R-AXIS RAPID diffractometer | 5070 independent reflections |
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995) | 3370 reflections with F2 > 2σ(F2) |
Tmin = 0.771, Tmax = 0.991 | Rint = 0.026 |
21193 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.38 e Å−3 |
5070 reflections | Δρmin = −0.26 e Å−3 |
281 parameters |
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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
F1 | 0.38293 (7) | 0.14318 (15) | −0.00934 (8) | 0.0871 (5) | |
O1 | 0.46981 (5) | 0.59709 (12) | 0.36061 (8) | 0.0510 (4) | |
O2 | 0.28907 (6) | 0.81844 (13) | 0.29527 (8) | 0.0559 (4) | |
O3 | 0.26165 (6) | 0.60434 (13) | 0.35157 (8) | 0.0541 (4) | |
O4 | 0.43779 (6) | 0.37861 (13) | 0.40222 (8) | 0.0528 (4) | |
C1 | 0.33939 (7) | 0.55677 (16) | 0.29460 (9) | 0.0374 (4) | |
C2 | 0.30171 (7) | 0.50860 (17) | 0.38325 (9) | 0.0410 (4) | |
C3 | 0.34468 (7) | 0.48284 (16) | 0.36326 (9) | 0.0374 (4) | |
C4 | 0.37305 (7) | 0.69315 (16) | 0.31271 (9) | 0.0394 (4) | |
C5 | 0.37392 (7) | 0.39250 (16) | 0.14693 (9) | 0.0397 (4) | |
C6 | 0.39243 (8) | 0.30729 (19) | 0.47009 (10) | 0.0478 (4) | |
C7 | 0.30055 (9) | 0.42833 (19) | 0.44439 (10) | 0.0490 (5) | |
C8 | 0.37200 (8) | 0.48601 (18) | 0.20228 (10) | 0.0435 (4) | |
C9 | 0.41934 (8) | 0.40838 (19) | 0.13113 (10) | 0.0468 (4) | |
C10 | 0.34759 (7) | 0.45888 (17) | 0.24304 (9) | 0.0401 (4) | |
C11 | 0.39165 (7) | 0.39240 (17) | 0.40863 (9) | 0.0412 (4) | |
C13 | 0.33133 (8) | 0.28989 (19) | 0.10782 (10) | 0.0492 (5) | |
C14 | 0.37988 (9) | 0.22567 (19) | 0.04230 (11) | 0.0533 (5) | |
C15 | 0.34225 (8) | 0.81682 (18) | 0.30644 (10) | 0.0449 (4) | |
C16 | 0.42251 (9) | 0.3253 (2) | 0.07889 (11) | 0.0541 (5) | |
C17 | 0.33405 (10) | 0.2057 (2) | 0.05524 (11) | 0.0567 (5) | |
C18 | 0.33098 (8) | 0.28697 (18) | 0.46091 (10) | 0.0467 (4) | |
C19 | 0.43444 (8) | 0.70204 (17) | 0.34034 (10) | 0.0446 (4) | |
C20 | 0.37073 (9) | 0.95534 (18) | 0.31481 (12) | 0.0566 (5) | |
C21 | 0.42333 (9) | 0.95511 (18) | 0.30305 (12) | 0.0533 (5) | |
C22 | 0.46479 (9) | 0.83836 (19) | 0.34999 (13) | 0.0596 (5) | |
C23 | 0.34063 (11) | 0.2288 (3) | 0.53606 (12) | 0.0654 (6) | |
C24 | 0.29292 (10) | 0.1860 (2) | 0.39620 (12) | 0.0598 (5) | |
C25 | 0.39917 (12) | 0.9295 (3) | 0.21754 (13) | 0.0734 (7) | |
C26 | 0.45606 (12) | 1.0926 (2) | 0.32438 (16) | 0.0802 (7) | |
H1 | 0.2969 | 0.5834 | 0.2640 | 0.0448* | |
H1A | 0.4545 | 0.5316 | 0.3695 | 0.0612* | |
H3 | 0.2730 | 0.6624 | 0.3329 | 0.0649* | |
H6A | 0.4190 | 0.3511 | 0.5190 | 0.0574* | |
H6B | 0.4092 | 0.2174 | 0.4711 | 0.0574* | |
H7A | 0.2590 | 0.4154 | 0.4298 | 0.0588* | |
H7B | 0.3202 | 0.4822 | 0.4910 | 0.0588* | |
H8 | 0.3906 (8) | 0.5785 (19) | 0.2057 (10) | 0.046 (5)* | |
H9 | 0.4482 | 0.4766 | 0.1564 | 0.0562* | |
H10 | 0.3290 (9) | 0.3665 (19) | 0.2366 (11) | 0.049 (5)* | |
H13 | 0.3004 | 0.2776 | 0.1171 | 0.0590* | |
H16 | 0.4531 | 0.3370 | 0.0688 | 0.0649* | |
H17 | 0.3054 | 0.1373 | 0.0294 | 0.0681* | |
H20A | 0.3844 | 0.9906 | 0.3655 | 0.0679* | |
H20B | 0.3404 | 1.0183 | 0.2783 | 0.0679* | |
H22A | 0.4950 | 0.8273 | 0.3365 | 0.0716* | |
H22B | 0.4854 | 0.8641 | 0.4035 | 0.0716* | |
H23A | 0.3030 | 0.2275 | 0.5339 | 0.0785* | |
H23B | 0.3687 | 0.2860 | 0.5778 | 0.0785* | |
H23C | 0.3562 | 0.1367 | 0.5435 | 0.0785* | |
H24A | 0.2882 | 0.2202 | 0.3495 | 0.0717* | |
H24B | 0.2541 | 0.1764 | 0.3904 | 0.0717* | |
H24C | 0.3125 | 0.0978 | 0.4080 | 0.0717* | |
H25A | 0.4321 | 0.9278 | 0.2093 | 0.0880* | |
H25B | 0.3719 | 1.0021 | 0.1877 | 0.0880* | |
H25C | 0.3785 | 0.8426 | 0.2025 | 0.0880* | |
H26A | 0.4855 | 1.0929 | 0.3098 | 0.0962* | |
H26B | 0.4757 | 1.1062 | 0.3785 | 0.0962* | |
H26C | 0.4277 | 1.1657 | 0.2983 | 0.0962* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.1116 (12) | 0.0874 (9) | 0.0818 (10) | −0.0026 (8) | 0.0642 (10) | −0.0334 (8) |
O1 | 0.0345 (7) | 0.0479 (7) | 0.0673 (9) | 0.0074 (5) | 0.0243 (6) | 0.0042 (6) |
O2 | 0.0429 (8) | 0.0621 (8) | 0.0646 (9) | 0.0186 (6) | 0.0295 (7) | 0.0060 (7) |
O3 | 0.0441 (8) | 0.0627 (8) | 0.0656 (9) | 0.0137 (6) | 0.0357 (7) | 0.0085 (7) |
O4 | 0.0414 (7) | 0.0620 (8) | 0.0626 (8) | 0.0166 (6) | 0.0325 (7) | 0.0123 (7) |
C1 | 0.0297 (8) | 0.0471 (9) | 0.0356 (8) | 0.0065 (7) | 0.0173 (7) | 0.0019 (7) |
C2 | 0.0348 (9) | 0.0497 (9) | 0.0396 (9) | 0.0011 (7) | 0.0203 (8) | −0.0048 (7) |
C3 | 0.0312 (8) | 0.0470 (9) | 0.0341 (8) | 0.0038 (7) | 0.0171 (7) | −0.0012 (7) |
C4 | 0.0359 (9) | 0.0440 (9) | 0.0370 (8) | 0.0066 (7) | 0.0183 (7) | 0.0001 (7) |
C5 | 0.0425 (9) | 0.0425 (9) | 0.0376 (8) | 0.0010 (7) | 0.0233 (8) | 0.0030 (7) |
C6 | 0.0443 (10) | 0.0582 (11) | 0.0366 (9) | 0.0051 (8) | 0.0182 (8) | 0.0064 (8) |
C7 | 0.0500 (11) | 0.0617 (11) | 0.0465 (10) | −0.0002 (9) | 0.0330 (9) | −0.0037 (9) |
C8 | 0.0456 (10) | 0.0447 (9) | 0.0456 (9) | −0.0018 (8) | 0.0276 (8) | −0.0010 (8) |
C9 | 0.0423 (10) | 0.0523 (10) | 0.0505 (10) | −0.0049 (8) | 0.0276 (9) | −0.0040 (8) |
C10 | 0.0388 (9) | 0.0448 (9) | 0.0378 (9) | 0.0026 (7) | 0.0208 (8) | 0.0008 (7) |
C11 | 0.0345 (9) | 0.0502 (9) | 0.0381 (9) | 0.0016 (7) | 0.0184 (7) | −0.0021 (7) |
C13 | 0.0482 (11) | 0.0565 (10) | 0.0516 (10) | −0.0086 (8) | 0.0322 (9) | −0.0017 (8) |
C14 | 0.0636 (12) | 0.0534 (10) | 0.0486 (10) | 0.0056 (9) | 0.0334 (10) | −0.0074 (9) |
C15 | 0.0422 (10) | 0.0504 (10) | 0.0409 (9) | 0.0109 (8) | 0.0208 (8) | 0.0018 (8) |
C16 | 0.0505 (11) | 0.0637 (12) | 0.0612 (12) | 0.0023 (9) | 0.0383 (10) | −0.0039 (10) |
C17 | 0.0617 (13) | 0.0527 (11) | 0.0549 (11) | −0.0141 (9) | 0.0301 (10) | −0.0109 (9) |
C18 | 0.0495 (11) | 0.0544 (10) | 0.0400 (9) | −0.0027 (8) | 0.0260 (9) | 0.0006 (8) |
C19 | 0.0395 (9) | 0.0458 (9) | 0.0466 (10) | 0.0051 (7) | 0.0213 (8) | −0.0018 (8) |
C20 | 0.0600 (13) | 0.0452 (10) | 0.0633 (12) | 0.0092 (9) | 0.0314 (11) | −0.0039 (9) |
C21 | 0.0591 (12) | 0.0418 (9) | 0.0634 (12) | 0.0028 (8) | 0.0350 (10) | −0.0007 (9) |
C22 | 0.0457 (11) | 0.0515 (11) | 0.0734 (14) | −0.0025 (9) | 0.0254 (11) | −0.0042 (10) |
C23 | 0.0763 (15) | 0.0750 (14) | 0.0540 (12) | −0.0025 (11) | 0.0405 (12) | 0.0084 (10) |
C24 | 0.0588 (13) | 0.0620 (12) | 0.0555 (12) | −0.0088 (10) | 0.0279 (10) | −0.0063 (10) |
C25 | 0.0962 (19) | 0.0677 (13) | 0.0680 (14) | −0.0037 (13) | 0.0512 (14) | 0.0025 (11) |
C26 | 0.0828 (18) | 0.0496 (12) | 0.106 (2) | −0.0079 (11) | 0.0482 (16) | −0.0115 (13) |
F1—C14 | 1.365 (3) | C21—C26 | 1.519 (3) |
O1—C19 | 1.288 (2) | O1—H1A | 0.820 |
O2—C15 | 1.284 (3) | O3—H3 | 0.820 |
O3—C2 | 1.291 (2) | C1—H1 | 0.980 |
O4—C11 | 1.286 (3) | C6—H6A | 0.970 |
C1—C3 | 1.524 (3) | C6—H6B | 0.970 |
C1—C4 | 1.522 (3) | C7—H7A | 0.970 |
C1—C10 | 1.519 (3) | C7—H7B | 0.970 |
C2—C3 | 1.405 (4) | C8—H8 | 1.01 (2) |
C2—C7 | 1.492 (3) | C9—H9 | 0.930 |
C3—C11 | 1.395 (2) | C10—H10 | 0.993 (19) |
C4—C15 | 1.412 (3) | C13—H13 | 0.930 |
C4—C19 | 1.395 (3) | C16—H16 | 0.930 |
C5—C8 | 1.476 (3) | C17—H17 | 0.930 |
C5—C9 | 1.393 (4) | C20—H20A | 0.970 |
C5—C13 | 1.392 (3) | C20—H20B | 0.970 |
C6—C11 | 1.501 (3) | C22—H22A | 0.970 |
C6—C18 | 1.527 (4) | C22—H22B | 0.970 |
C7—C18 | 1.531 (3) | C23—H23A | 0.960 |
C8—C10 | 1.318 (4) | C23—H23B | 0.960 |
C9—C16 | 1.379 (4) | C23—H23C | 0.960 |
C13—C17 | 1.386 (4) | C24—H24A | 0.960 |
C14—C16 | 1.364 (3) | C24—H24B | 0.960 |
C14—C17 | 1.369 (4) | C24—H24C | 0.960 |
C15—C20 | 1.501 (3) | C25—H25A | 0.960 |
C18—C23 | 1.537 (4) | C25—H25B | 0.960 |
C18—C24 | 1.527 (3) | C25—H25C | 0.960 |
C19—C22 | 1.500 (3) | C26—H26A | 0.960 |
C20—C21 | 1.514 (4) | C26—H26B | 0.960 |
C21—C22 | 1.513 (3) | C26—H26C | 0.960 |
C21—C25 | 1.546 (4) | ||
O1···O4 | 2.582 (2) | H25A···H26C | 2.9839 |
O1···C1 | 2.958 (2) | H25B···H26A | 2.8412 |
O1···C3 | 3.478 (3) | H25B···H26B | 3.5526 |
O1···C8 | 3.094 (2) | H25B···H26C | 2.5181 |
O1···C10 | 3.1214 (18) | H25C···H26A | 3.4790 |
O1···C11 | 3.345 (3) | H25C···H26C | 3.5627 |
O2···O3 | 2.652 (3) | F1···H3i | 3.5443 |
O2···C1 | 2.861 (3) | F1···H20Ai | 2.8996 |
O2···C2 | 3.432 (3) | F1···H23Cxi | 3.1345 |
O2···C3 | 3.539 (2) | F1···H24Cxi | 2.9076 |
O2···C19 | 3.586 (3) | F1···H26Bviii | 3.2540 |
O3···C1 | 2.863 (3) | O1···H6Aii | 2.6989 |
O3···C4 | 3.504 (3) | O1···H9iii | 2.6183 |
O3···C11 | 3.599 (3) | O1···H16iii | 3.0762 |
O3···C15 | 3.403 (3) | O2···H1v | 3.2037 |
O4···C1 | 2.9201 (19) | O2···H10v | 2.84 (3) |
O4···C2 | 3.594 (3) | O2···H24Av | 2.7478 |
O4···C4 | 3.505 (2) | O2···H24Cix | 3.4056 |
O4···C10 | 2.9649 (19) | O3···H10v | 3.295 (18) |
O4···C19 | 3.368 (3) | O3···H13v | 2.6374 |
C2···C4 | 3.407 (3) | O3···H20Bvii | 2.7334 |
C2···C6 | 2.860 (3) | O3···H25Bvii | 3.2933 |
C2···C24 | 3.158 (3) | O4···H16iii | 2.6202 |
C3···C15 | 3.432 (3) | O4···H26Bvi | 2.9496 |
C3···C18 | 2.919 (3) | O4···H26Cvi | 2.8821 |
C3···C19 | 3.375 (3) | C1···H24Av | 3.4711 |
C3···C24 | 3.396 (3) | C1···H24Bv | 3.4705 |
C4···C8 | 3.021 (3) | C2···H20Bvii | 3.4491 |
C4···C11 | 3.410 (3) | C5···H7Bi | 3.0013 |
C4···C21 | 2.913 (3) | C5···H23Bi | 3.3995 |
C4···C25 | 3.308 (4) | C5···H26Cvi | 3.4528 |
C5···C14 | 2.761 (3) | C6···H22Bii | 3.3179 |
C7···C11 | 2.856 (4) | C7···H23Axii | 3.3259 |
C8···C19 | 3.203 (3) | C8···H23Bi | 3.3493 |
C9···C17 | 2.760 (3) | C8···H24Bv | 3.3632 |
C10···C11 | 3.038 (3) | C8···H26Cvi | 3.5574 |
C10···C13 | 3.059 (3) | C9···H1Aiii | 3.5108 |
C10···C19 | 3.155 (3) | C9···H6Ai | 3.2768 |
C11···C24 | 3.167 (4) | C9···H7Bi | 2.8835 |
C13···C16 | 2.761 (4) | C9···H23Bi | 3.1961 |
C15···C22 | 2.843 (4) | C10···H24Bv | 3.3756 |
C15···C25 | 3.097 (5) | C10···H26Cvi | 3.3555 |
C19···C20 | 2.857 (3) | C13···H7Bi | 3.1625 |
C19···C25 | 3.107 (3) | C13···H17xiii | 3.2645 |
F1···O2i | 3.4600 (19) | C13···H25Bvi | 3.1280 |
F1···C15i | 3.378 (3) | C13···H26Cvi | 3.5780 |
F1···C20i | 3.589 (4) | C14···H7Bi | 3.1374 |
O1···C6ii | 3.5777 (18) | C14···H23Cxi | 3.5700 |
O1···C9iii | 3.353 (3) | C14···H26Aviii | 3.4741 |
O1···C16iii | 3.569 (3) | C14···H26Bviii | 3.4324 |
O2···F1iv | 3.4600 (19) | C15···H24Av | 3.3645 |
O2···C10v | 3.502 (3) | C16···H1Aiii | 3.4456 |
O2···C24v | 3.592 (3) | C16···H6Ai | 3.3549 |
O3···C13v | 3.458 (3) | C16···H7Bi | 2.9717 |
O4···C16iii | 3.499 (3) | C16···H26Aviii | 3.2142 |
O4···C26vi | 3.358 (4) | C16···H26Bviii | 3.1474 |
C6···O1ii | 3.5777 (18) | C17···H7Bi | 3.2451 |
C9···O1iii | 3.353 (3) | C17···H13xiii | 3.4469 |
C10···O2vii | 3.502 (3) | C17···H17xiii | 3.4602 |
C13···O3vii | 3.458 (3) | C17···H23Cxi | 3.4005 |
C15···F1iv | 3.378 (3) | C17···H25Bvi | 3.0778 |
C16···O1iii | 3.569 (3) | C18···H23Axii | 3.5590 |
C16···O4iii | 3.499 (3) | C19···H6Aii | 3.4183 |
C16···C26viii | 3.535 (3) | C20···H24Cix | 3.3082 |
C20···F1iv | 3.589 (4) | C22···H6Aii | 3.3583 |
C23···C25iv | 3.556 (4) | C22···H6Bii | 3.4608 |
C24···O2vii | 3.592 (3) | C22···H25Aiii | 3.5958 |
C25···C23i | 3.556 (4) | C23···H7Axii | 3.3374 |
C26···O4ix | 3.358 (4) | C23···H8iv | 3.55 (2) |
C26···C16x | 3.535 (3) | C23···H23Axii | 3.2657 |
F1···H16 | 2.5265 | C23···H25Aiv | 3.4340 |
F1···H17 | 2.5341 | C23···H25Biv | 3.5689 |
O1···H8 | 2.749 (17) | C23···H25Civ | 3.1025 |
O1···H22A | 2.4503 | C24···H1vii | 3.0411 |
O1···H22B | 2.6959 | C24···H20Avi | 3.3570 |
O2···H1 | 2.4058 | C24···H23Axii | 3.5806 |
O2···H3 | 1.8447 | C25···H23Ai | 3.5987 |
O2···H20A | 2.7014 | C25···H23Bi | 3.2955 |
O2···H20B | 2.4821 | C25···H23Ci | 3.2059 |
O3···H1 | 2.4234 | C26···H16x | 3.2570 |
O3···H7A | 2.4622 | H1···O2vii | 3.2037 |
O3···H7B | 2.7150 | H1···C24v | 3.0411 |
O4···H1A | 1.7755 | H1···H20Bvii | 3.2784 |
O4···H6A | 2.7041 | H1···H24Av | 2.5911 |
O4···H6B | 2.4732 | H1···H24Bv | 2.8692 |
O4···H10 | 3.090 (16) | H1···H24Cv | 3.1795 |
C1···H1A | 2.5724 | H1A···C9iii | 3.5108 |
C1···H3 | 2.4700 | H1A···C16iii | 3.4456 |
C1···H8 | 2.78 (3) | H1A···H6Aii | 3.0874 |
C2···H1 | 2.4971 | H1A···H9iii | 2.9050 |
C2···H6A | 3.2475 | H1A···H16iii | 2.7913 |
C2···H24A | 2.8580 | H3···F1iv | 3.5443 |
C2···H24B | 3.4831 | H3···H10v | 3.0122 |
C3···H1A | 2.8426 | H3···H13v | 2.8370 |
C3···H3 | 2.3869 | H3···H20Bvii | 2.9758 |
C3···H6A | 3.0234 | H3···H24Av | 3.2648 |
C3···H6B | 3.2346 | H6A···O1ii | 2.6989 |
C3···H7A | 3.2415 | H6A···C9iv | 3.2768 |
C3···H7B | 3.0127 | H6A···C16iv | 3.3549 |
C3···H10 | 2.67 (3) | H6A···C19ii | 3.4183 |
C3···H24A | 2.8821 | H6A···C22ii | 3.3583 |
C4···H1A | 2.3956 | H6A···H1Aii | 3.0874 |
C4···H3 | 2.8668 | H6A···H9iv | 3.0169 |
C4···H8 | 2.71 (3) | H6A···H16iv | 3.1682 |
C4···H10 | 3.452 (18) | H6A···H22Aii | 3.1425 |
C4···H20A | 3.0406 | H6A···H22Bii | 2.9929 |
C4···H20B | 3.2454 | H6B···C22ii | 3.4608 |
C4···H22A | 3.2316 | H6B···H20Avi | 2.9153 |
C4···H22B | 3.0167 | H6B···H22Aii | 3.4254 |
C4···H25C | 2.7559 | H6B···H22Bii | 2.7239 |
C5···H10 | 2.66 (3) | H6B···H26Bvi | 3.3576 |
C5···H16 | 3.2585 | H7A···C23xii | 3.3374 |
C5···H17 | 3.2614 | H7A···H17v | 3.1063 |
C6···H7A | 3.3010 | H7A···H23Axii | 2.5240 |
C6···H7B | 2.7340 | H7A···H23Cxii | 3.3690 |
C6···H23A | 3.3140 | H7A···H25Bvii | 3.0946 |
C6···H23B | 2.6019 | H7A···H25Cvii | 3.2487 |
C6···H23C | 2.7206 | H7B···C5iv | 3.0013 |
C6···H24A | 2.6832 | H7B···C9iv | 2.8835 |
C6···H24B | 3.3376 | H7B···C13iv | 3.1625 |
C6···H24C | 2.7056 | H7B···C14iv | 3.1374 |
C7···H3 | 3.0328 | H7B···C16iv | 2.9717 |
C7···H6A | 2.7402 | H7B···C17iv | 3.2451 |
C7···H6B | 3.3008 | H7B···H9iv | 3.3151 |
C7···H23A | 2.6568 | H7B···H16iv | 3.4437 |
C7···H23B | 2.7355 | H7B···H17v | 3.4281 |
C7···H23C | 3.3399 | H8···C23i | 3.55 (2) |
C7···H24A | 2.7057 | H8···H23Ai | 3.5752 |
C7···H24B | 2.6945 | H8···H23Bi | 2.7186 |
C7···H24C | 3.3429 | H8···H24Bv | 3.3563 |
C8···H1 | 2.9917 | H9···O1iii | 2.6183 |
C8···H1A | 2.9829 | H9···H1Aiii | 2.9050 |
C8···H9 | 2.6130 | H9···H6Ai | 3.0169 |
C8···H13 | 2.6860 | H9···H7Bi | 3.3151 |
C8···H25C | 3.4618 | H9···H9iii | 3.3508 |
C9···H8 | 2.62 (3) | H9···H23Bi | 2.9511 |
C9···H13 | 3.2248 | H10···O2vii | 2.84 (3) |
C10···H1A | 2.7289 | H10···O3vii | 3.295 (18) |
C10···H13 | 2.8230 | H10···H3vii | 3.0122 |
C11···H1 | 3.2688 | H10···H20Bvi | 3.4585 |
C11···H1A | 2.5590 | H10···H26Cvi | 2.9353 |
C11···H7B | 3.2294 | H13···O3vii | 2.6374 |
C11···H10 | 3.03 (2) | H13···C17xiii | 3.4469 |
C11···H24A | 2.8507 | H13···H3vii | 2.8370 |
C11···H24C | 3.5218 | H13···H17xiii | 2.9453 |
C13···H8 | 3.319 (18) | H13···H25Bvi | 3.1443 |
C13···H9 | 3.2243 | H16···O1iii | 3.0762 |
C13···H10 | 2.78 (3) | H16···O4iii | 2.6202 |
C14···H9 | 3.1969 | H16···C26viii | 3.2570 |
C14···H13 | 3.2053 | H16···H1Aiii | 2.7913 |
C15···H1 | 2.4902 | H16···H6Ai | 3.1682 |
C15···H3 | 2.6145 | H16···H7Bi | 3.4437 |
C15···H22B | 3.2173 | H16···H26Aviii | 3.1956 |
C15···H25B | 3.4305 | H16···H26Bviii | 2.7439 |
C15···H25C | 2.7652 | H16···H26Cviii | 3.3177 |
C16···H17 | 3.2322 | H17···C13xiii | 3.2645 |
C17···H16 | 3.2321 | H17···C17xiii | 3.4602 |
C19···H1 | 3.2823 | H17···H7Avii | 3.1063 |
C19···H8 | 2.663 (19) | H17···H7Bvii | 3.4281 |
C19···H20A | 3.2423 | H17···H13xiii | 2.9453 |
C19···H25A | 3.4469 | H17···H17xiii | 3.3099 |
C19···H25C | 2.7731 | H17···H23Axi | 3.5394 |
C20···H22A | 3.2797 | H17···H23Cxi | 2.9151 |
C20···H22B | 2.7119 | H17···H24Cxi | 3.4557 |
C20···H25A | 3.3149 | H17···H25Bvi | 3.0675 |
C20···H25B | 2.6686 | H20A···F1iv | 2.8996 |
C20···H25C | 2.6571 | H20A···C24ix | 3.3570 |
C20···H26A | 3.3304 | H20A···H6Bix | 2.9153 |
C20···H26B | 2.7584 | H20A···H24Aix | 3.2422 |
C20···H26C | 2.6485 | H20A···H24Cix | 2.6614 |
C22···H1A | 3.0318 | H20B···O3v | 2.7334 |
C22···H8 | 3.590 (18) | H20B···C2v | 3.4491 |
C22···H20A | 2.7190 | H20B···H1v | 3.2784 |
C22···H20B | 3.2793 | H20B···H3v | 2.9758 |
C22···H25A | 2.6944 | H20B···H10ix | 3.4585 |
C22···H25B | 3.3258 | H20B···H24Aix | 3.1516 |
C22···H25C | 2.6684 | H20B···H24Cix | 3.2052 |
C22···H26A | 2.7448 | H22A···H6Aii | 3.1425 |
C22···H26B | 2.6447 | H22A···H6Bii | 3.4254 |
C22···H26C | 3.3257 | H22A···H23Bii | 3.2262 |
C23···H6A | 2.5432 | H22A···H23Cii | 3.3559 |
C23···H6B | 2.7395 | H22A···H25Aiii | 2.7089 |
C23···H7A | 2.7768 | H22B···C6ii | 3.3179 |
C23···H7B | 2.5806 | H22B···H6Aii | 2.9929 |
C23···H24A | 3.3302 | H22B···H6Bii | 2.7239 |
C23···H24B | 2.6919 | H23A···C7xii | 3.3259 |
C23···H24C | 2.6575 | H23A···C18xii | 3.5590 |
C24···H6A | 3.3266 | H23A···C23xii | 3.2657 |
C24···H6B | 2.6039 | H23A···C24xii | 3.5806 |
C24···H7A | 2.6170 | H23A···C25iv | 3.5987 |
C24···H7B | 3.3328 | H23A···H7Axii | 2.5240 |
C24···H23A | 2.7323 | H23A···H8iv | 3.5752 |
C24···H23B | 3.3254 | H23A···H17xiv | 3.5394 |
C24···H23C | 2.6241 | H23A···H23Axii | 2.3987 |
C25···H8 | 3.411 (19) | H23A···H24Bxii | 2.8208 |
C25···H20A | 3.3152 | H23A···H25Biv | 3.4980 |
C25···H20B | 2.5823 | H23A···H25Civ | 3.0346 |
C25···H22A | 2.6105 | H23B···C5iv | 3.3995 |
C25···H22B | 3.3273 | H23B···C8iv | 3.3493 |
C25···H26A | 2.5899 | H23B···C9iv | 3.1961 |
C25···H26B | 3.3102 | H23B···C25iv | 3.2955 |
C25···H26C | 2.6949 | H23B···H8iv | 2.7186 |
C26···H20A | 2.6190 | H23B···H9iv | 2.9511 |
C26···H20B | 2.7469 | H23B···H22Aii | 3.2262 |
C26···H22A | 2.7291 | H23B···H25Aiv | 3.1085 |
C26···H22B | 2.6149 | H23B···H25Biv | 3.5664 |
C26···H25A | 2.6442 | H23B···H25Civ | 2.7403 |
C26···H25B | 2.6512 | H23C···F1xiv | 3.1345 |
C26···H25C | 3.3080 | H23C···C14xiv | 3.5700 |
H1···H1A | 3.5404 | H23C···C17xiv | 3.4005 |
H1···H3 | 1.9773 | H23C···C25iv | 3.2059 |
H1···H8 | 3.2400 | H23C···H7Axii | 3.3690 |
H1···H10 | 2.4367 | H23C···H17xiv | 2.9151 |
H1A···H8 | 2.9071 | H23C···H22Aii | 3.3559 |
H1A···H10 | 3.3743 | H23C···H25Aiv | 2.9786 |
H1A···H22A | 3.2484 | H23C···H25Biv | 3.0829 |
H1A···H22B | 3.3076 | H23C···H25Civ | 3.0132 |
H3···H7A | 3.2561 | H24A···O2vii | 2.7478 |
H3···H7B | 3.3091 | H24A···C1vii | 3.4711 |
H6A···H7B | 2.6557 | H24A···C15vii | 3.3645 |
H6A···H23A | 3.4169 | H24A···H1vii | 2.5911 |
H6A···H23B | 2.2912 | H24A···H3vii | 3.2648 |
H6A···H23C | 2.8504 | H24A···H20Avi | 3.2422 |
H6A···H24A | 3.5984 | H24A···H20Bvi | 3.1516 |
H6A···H24C | 3.5100 | H24B···C1vii | 3.4705 |
H6B···H23B | 2.9667 | H24B···C8vii | 3.3632 |
H6B···H23C | 2.6258 | H24B···C10vii | 3.3756 |
H6B···H24A | 2.8206 | H24B···H1vii | 2.8692 |
H6B···H24B | 3.5017 | H24B···H8vii | 3.3563 |
H6B···H24C | 2.4427 | H24B···H23Axii | 2.8208 |
H7A···H23A | 2.5778 | H24B···H25Cvii | 3.3627 |
H7A···H23B | 3.1479 | H24C···F1xiv | 2.9076 |
H7A···H24A | 2.8632 | H24C···O2vi | 3.4056 |
H7A···H24B | 2.4360 | H24C···C20vi | 3.3082 |
H7A···H24C | 3.5057 | H24C···H1vii | 3.1795 |
H7B···H23A | 2.7369 | H24C···H17xiv | 3.4557 |
H7B···H23B | 2.4577 | H24C···H20Avi | 2.6614 |
H7B···H23C | 3.4938 | H24C···H20Bvi | 3.2052 |
H7B···H24B | 3.5089 | H25A···C22iii | 3.5958 |
H8···H9 | 2.4215 | H25A···C23i | 3.4340 |
H8···H10 | 2.88 (4) | H25A···H22Aiii | 2.7089 |
H8···H13 | 3.5893 | H25A···H23Bi | 3.1085 |
H8···H22A | 3.5787 | H25A···H23Ci | 2.9786 |
H8···H25A | 3.5445 | H25A···H25Aiii | 3.0256 |
H8···H25C | 2.5769 | H25A···H26Aiii | 2.8698 |
H9···H16 | 2.3086 | H25B···O3v | 3.2933 |
H10···H13 | 2.3260 | H25B···C13ix | 3.1280 |
H10···H24A | 3.3387 | H25B···C17ix | 3.0778 |
H13···H17 | 2.3178 | H25B···C23i | 3.5689 |
H20A···H22B | 2.6301 | H25B···H7Av | 3.0946 |
H20A···H25B | 3.4985 | H25B···H13ix | 3.1443 |
H20A···H25C | 3.5747 | H25B···H17ix | 3.0675 |
H20A···H26A | 3.5269 | H25B···H23Ai | 3.4980 |
H20A···H26B | 2.5201 | H25B···H23Bi | 3.5664 |
H20A···H26C | 2.7765 | H25B···H23Ci | 3.0829 |
H20B···H25A | 3.4755 | H25C···C23i | 3.1025 |
H20B···H25B | 2.4038 | H25C···H7Av | 3.2487 |
H20B···H25C | 2.8185 | H25C···H23Ai | 3.0346 |
H20B···H26A | 3.5677 | H25C···H23Bi | 2.7403 |
H20B···H26B | 3.1360 | H25C···H23Ci | 3.0132 |
H20B···H26C | 2.5353 | H25C···H24Bv | 3.3627 |
H22A···H25A | 2.4463 | H26A···C14x | 3.4741 |
H22A···H25B | 3.5021 | H26A···C16x | 3.2142 |
H22A···H25C | 2.8446 | H26A···H16x | 3.1956 |
H22A···H26A | 2.6175 | H26A···H25Aiii | 2.8698 |
H22A···H26B | 2.9612 | H26A···H26Aiii | 2.9284 |
H22B···H25A | 3.5263 | H26B···F1x | 3.2540 |
H22B···H25C | 3.5821 | H26B···O4ix | 2.9496 |
H22B···H26A | 2.9391 | H26B···C14x | 3.4324 |
H22B···H26B | 2.3881 | H26B···C16x | 3.1474 |
H22B···H26C | 3.4761 | H26B···H6Bix | 3.3576 |
H23A···H24B | 2.5761 | H26B···H16x | 2.7439 |
H23A···H24C | 3.0027 | H26C···O4ix | 2.8821 |
H23B···H24B | 3.5851 | H26C···C5ix | 3.4528 |
H23B···H24C | 3.5078 | H26C···C8ix | 3.5574 |
H23C···H24A | 3.5058 | H26C···C10ix | 3.3555 |
H23C···H24B | 2.8935 | H26C···C13ix | 3.5780 |
H23C···H24C | 2.4234 | H26C···H10ix | 2.9353 |
H25A···H26A | 2.3988 | H26C···H16x | 3.3177 |
H25A···H26B | 3.4989 | ||
C3—C1—C4 | 114.93 (13) | C11—C6—H6B | 108.604 |
C3—C1—C10 | 112.04 (14) | C18—C6—H6A | 108.596 |
C4—C1—C10 | 116.04 (18) | C18—C6—H6B | 108.601 |
O3—C2—C3 | 122.72 (19) | H6A—C6—H6B | 107.561 |
O3—C2—C7 | 115.6 (2) | C2—C7—H7A | 108.609 |
C3—C2—C7 | 121.71 (15) | C2—C7—H7B | 108.601 |
C1—C3—C2 | 119.27 (14) | C18—C7—H7A | 108.608 |
C1—C3—C11 | 122.46 (19) | C18—C7—H7B | 108.602 |
C2—C3—C11 | 118.26 (18) | H7A—C7—H7B | 107.579 |
C1—C4—C15 | 119.16 (16) | C5—C8—H8 | 113.0 (15) |
C1—C4—C19 | 123.12 (15) | C10—C8—H8 | 120.8 (15) |
C15—C4—C19 | 117.58 (15) | C5—C9—H9 | 119.245 |
C8—C5—C9 | 119.27 (15) | C16—C9—H9 | 119.224 |
C8—C5—C13 | 123.0 (2) | C1—C10—H10 | 114.8 (16) |
C9—C5—C13 | 117.69 (19) | C8—C10—H10 | 117.3 (15) |
C11—C6—C18 | 114.65 (14) | C5—C13—H13 | 119.337 |
C2—C7—C18 | 114.6 (2) | C17—C13—H13 | 119.338 |
C5—C8—C10 | 126.20 (17) | C9—C16—H16 | 120.715 |
C5—C9—C16 | 121.53 (17) | C14—C16—H16 | 120.700 |
C1—C10—C8 | 127.65 (16) | C13—C17—H17 | 120.792 |
O4—C11—C3 | 122.67 (19) | C14—C17—H17 | 120.814 |
O4—C11—C6 | 115.41 (15) | C15—C20—H20A | 108.602 |
C3—C11—C6 | 121.9 (2) | C15—C20—H20B | 108.605 |
C5—C13—C17 | 121.3 (3) | C21—C20—H20A | 108.614 |
F1—C14—C16 | 118.7 (3) | C21—C20—H20B | 108.604 |
F1—C14—C17 | 118.79 (17) | H20A—C20—H20B | 107.564 |
C16—C14—C17 | 122.5 (3) | C19—C22—H22A | 108.521 |
O2—C15—C4 | 122.55 (17) | C19—C22—H22B | 108.501 |
O2—C15—C20 | 115.74 (17) | C21—C22—H22A | 108.517 |
C4—C15—C20 | 121.69 (19) | C21—C22—H22B | 108.512 |
C9—C16—C14 | 118.6 (3) | H22A—C22—H22B | 107.534 |
C13—C17—C14 | 118.39 (19) | C18—C23—H23A | 109.468 |
C6—C18—C7 | 107.56 (17) | C18—C23—H23B | 109.479 |
C6—C18—C23 | 108.35 (15) | C18—C23—H23C | 109.468 |
C6—C18—C24 | 110.6 (2) | H23A—C23—H23B | 109.472 |
C7—C18—C23 | 110.1 (2) | H23A—C23—H23C | 109.462 |
C7—C18—C24 | 110.84 (13) | H23B—C23—H23C | 109.478 |
C23—C18—C24 | 109.27 (18) | C18—C24—H24A | 109.473 |
O1—C19—C4 | 124.01 (16) | C18—C24—H24B | 109.467 |
O1—C19—C22 | 114.44 (17) | C18—C24—H24C | 109.473 |
C4—C19—C22 | 121.55 (16) | H24A—C24—H24B | 109.461 |
C15—C20—C21 | 114.63 (18) | H24A—C24—H24C | 109.482 |
C20—C21—C22 | 107.8 (2) | H24B—C24—H24C | 109.472 |
C20—C21—C25 | 108.55 (18) | C21—C25—H25A | 109.474 |
C20—C21—C26 | 111.9 (2) | C21—C25—H25B | 109.462 |
C22—C21—C25 | 109.5 (2) | C21—C25—H25C | 109.465 |
C22—C21—C26 | 111.47 (16) | H25A—C25—H25B | 109.488 |
C25—C21—C26 | 107.6 (3) | H25A—C25—H25C | 109.479 |
C19—C22—C21 | 115.02 (16) | H25B—C25—H25C | 109.459 |
C19—O1—H1A | 109.456 | C21—C26—H26A | 109.470 |
C2—O3—H3 | 109.461 | C21—C26—H26B | 109.469 |
C3—C1—H1 | 104.006 | C21—C26—H26C | 109.472 |
C4—C1—H1 | 104.005 | H26A—C26—H26B | 109.472 |
C10—C1—H1 | 104.004 | H26A—C26—H26C | 109.471 |
C11—C6—H6A | 108.608 | H26B—C26—H26C | 109.473 |
C3—C1—C4—C15 | −93.59 (17) | C8—C5—C13—C17 | 178.82 (13) |
C3—C1—C4—C19 | 82.0 (3) | C13—C5—C8—C10 | 26.9 (3) |
C4—C1—C3—C2 | 91.11 (17) | C9—C5—C13—C17 | 0.4 (3) |
C4—C1—C3—C11 | −87.27 (19) | C13—C5—C9—C16 | −0.3 (3) |
C3—C1—C10—C8 | −146.85 (13) | C11—C6—C18—C7 | −47.8 (2) |
C10—C1—C3—C2 | −133.63 (14) | C11—C6—C18—C23 | −166.88 (14) |
C10—C1—C3—C11 | 48.00 (18) | C11—C6—C18—C24 | 73.35 (18) |
C4—C1—C10—C8 | −12.11 (19) | C18—C6—C11—O4 | −160.81 (14) |
C10—C1—C4—C15 | 132.97 (15) | C18—C6—C11—C3 | 20.9 (3) |
C10—C1—C4—C19 | −51.4 (2) | C2—C7—C18—C6 | 48.65 (17) |
O3—C2—C3—C1 | −8.3 (2) | C2—C7—C18—C23 | 166.54 (12) |
O3—C2—C3—C11 | 170.12 (12) | C2—C7—C18—C24 | −72.4 (2) |
O3—C2—C7—C18 | 158.96 (13) | C5—C8—C10—C1 | −173.56 (12) |
C3—C2—C7—C18 | −22.5 (2) | C5—C9—C16—C14 | −0.0 (3) |
C7—C2—C3—C1 | 173.21 (12) | C5—C13—C17—C14 | −0.1 (3) |
C7—C2—C3—C11 | −8.3 (2) | F1—C14—C16—C9 | −179.91 (14) |
C1—C3—C11—O4 | 9.4 (3) | F1—C14—C17—C13 | 179.96 (14) |
C1—C3—C11—C6 | −172.44 (12) | C16—C14—C17—C13 | −0.3 (3) |
C2—C3—C11—O4 | −169.00 (13) | C17—C14—C16—C9 | 0.3 (3) |
C2—C3—C11—C6 | 9.2 (2) | O2—C15—C20—C21 | −161.68 (15) |
C1—C4—C15—O2 | 8.9 (3) | C4—C15—C20—C21 | 20.0 (3) |
C1—C4—C15—C20 | −172.97 (15) | O1—C19—C22—C21 | 159.85 (19) |
C1—C4—C19—O1 | −7.4 (4) | C4—C19—C22—C21 | −21.1 (4) |
C1—C4—C19—C22 | 173.69 (16) | C15—C20—C21—C22 | −48.2 (2) |
C15—C4—C19—O1 | 168.26 (18) | C15—C20—C21—C25 | 70.38 (18) |
C15—C4—C19—C22 | −10.7 (3) | C15—C20—C21—C26 | −171.05 (14) |
C19—C4—C15—O2 | −166.96 (17) | C20—C21—C22—C19 | 48.9 (3) |
C19—C4—C15—C20 | 11.2 (3) | C25—C21—C22—C19 | −69.0 (3) |
C8—C5—C9—C16 | −178.84 (13) | C26—C21—C22—C19 | 172.0 (3) |
C9—C5—C8—C10 | −154.65 (15) |
Symmetry codes: (i) x, −y+1, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1, y, −z+1/2; (iv) x, −y+1, z+1/2; (v) −x+1/2, y+1/2, −z+1/2; (vi) x, y−1, z; (vii) −x+1/2, y−1/2, −z+1/2; (viii) −x+1, y−1, −z+1/2; (ix) x, y+1, z; (x) −x+1, y+1, −z+1/2; (xi) x, −y, z−1/2; (xii) −x+1/2, −y+1/2, −z+1; (xiii) −x+1/2, −y+1/2, −z; (xiv) x, −y, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O4 | 0.82 | 1.78 | 2.582 (2) | 168 |
O3—H3···O2 | 0.82 | 1.85 | 2.652 (3) | 168 |
C9—H9···O1iii | 0.93 | 2.62 | 3.353 (3) | 136 |
C16—H16···O4iii | 0.93 | 2.62 | 3.499 (3) | 158 |
Symmetry code: (iii) −x+1, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C25H29FO4 |
Mr | 412.50 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 296 |
a, b, c (Å) | 26.1146 (13), 9.6961 (4), 20.5638 (9) |
β (°) | 121.5921 (15) |
V (Å3) | 4435.3 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Rigaku, 1995) |
Tmin, Tmax | 0.771, 0.991 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 21193, 5070, 3370 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.158, 1.09 |
No. of reflections | 5070 |
No. of parameters | 281 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.38, −0.26 |
Computer programs: RAPID-AUTO (Rigaku, 2006), Il Milione (Burla et al., 2007), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O4 | 0.82 | 1.78 | 2.582 (2) | 168 |
O3—H3···O2 | 0.82 | 1.85 | 2.652 (3) | 168 |
C9—H9···O1i | 0.93 | 2.62 | 3.353 (3) | 136 |
C16—H16···O4i | 0.93 | 2.62 | 3.499 (3) | 158 |
Symmetry code: (i) −x+1, y, −z+1/2. |
Acknowledgements
Fiancial support from the Korea Institute of Science and Technology (KIST) is gratefully acknowledged.
References
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609–613. Web of Science CrossRef CAS IUCr Journals Google Scholar
Cha, J. H., Cho, Y. S., Lee, J. K., Park, J. & Sato, H. (2012). Acta Cryst. E68, o2510. CSD CrossRef IUCr Journals Google Scholar
Cha, J. H., Kim, Y. H., Min, S.-J., Cho, Y. S. & Lee, J. K. (2011). Acta Cryst. E67, o3153. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
As a part of our ongoing study of the substituent effect on the solide state structures of two cyclohexenone ring derivatives (Cha et al., 2011, 2012), we present here the title compound (I).
In (I) (Fig. 1), the bond lengths and angles are normal and correspond to those observed in related structures (Cha et al., 2011, 2012). Two cyclohexenone rings show an envelope conformation. The dihedral angle between the cyclohexenone mean planes is 41.08 (75)° while the dihedral angles between the benzene ring and the two cyclohexenone mean planes are 53.97 (75)° and 79.79 (14)°, respectively. In the crystal, weak intermolecular C—H···O hydrogen bonds (Table 1) link molecules into centrosymmetric dimers.