organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

(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

(Received 8 February 2013; accepted 14 February 2013; online 20 February 2013)

In the title compound, C25H29FO4, each cyclo­hexenone ring has an envelope conformation 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[Cha, J. H., Kim, Y. H., Min, S.-J., Cho, Y. S. & Lee, J. K. (2011). Acta Cryst. E67, o3153.], 2012[Cha, J. H., Cho, Y. S., Lee, J. K., Park, J. & Sato, H. (2012). Acta Cryst. E68, o2510.]).

[Scheme 1]

Experimental

Crystal data
  • C25H29FO4

  • Mr = 412.50

  • Monoclinic, C 2/c

  • a = 26.1146 (13) Å

  • b = 9.6961 (4) Å

  • c = 20.5638 (9) Å

  • β = 121.5921 (15)°

  • V = 4435.3 (4) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Rigaku, 1995[Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.771, Tmax = 0.991

  • 21193 measured reflections

  • 5070 independent reflections

  • 3370 reflections with F2 > 2σ(F2)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.158

  • S = 1.09

  • 5070 reflections

  • 281 parameters

  • H-atom parameters constrained

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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+{\script{1\over 2}}].

Data collection: RAPID-AUTO (Rigaku, 2006[Rigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: Il Milione (Burla et al., 2007[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.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); software used to prepare material for publication: CrystalStructure.

Supporting information


Comment top

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.

Related literature top

For the crystal structures of related xanthenes derivatives, see: Cha et al. (2011, 2012).

Experimental top

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 column chromatography to afford the title compound as a colorless solid in yield 82%. Recrystallization from ethanol gave crystals suitable for X-ray analysis.

Refinement top

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).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2006); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atomic numbering and 50% probability displacement ellipsoid.
(E)-2,2'-[3-(4-Fluorophenyl)prop-2-ene-1,1-diyl]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one) top
Crystal data top
C25H29FO4F(000) = 1760.00
Mr = 412.50Dx = 1.235 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71075 Å
Hall symbol: -C 2ycCell parameters from 14685 reflections
a = 26.1146 (13) Åθ = 3.2–27.5°
b = 9.6961 (4) ŵ = 0.09 mm1
c = 20.5638 (9) ÅT = 296 K
β = 121.5921 (15)°Block, colourless
V = 4435.3 (4) Å30.30 × 0.20 × 0.10 mm
Z = 8
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3370 reflections with F2 > 2σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.026
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
h = 3333
Tmin = 0.771, Tmax = 0.991k = 1012
21193 measured reflectionsl = 2626
5070 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158H-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 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.26 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C25H29FO4V = 4435.3 (4) Å3
Mr = 412.50Z = 8
Monoclinic, C2/cMo Kα radiation
a = 26.1146 (13) ŵ = 0.09 mm1
b = 9.6961 (4) ÅT = 296 K
c = 20.5638 (9) Å0.30 × 0.20 × 0.10 mm
β = 121.5921 (15)°
Data collection top
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 = 0.991Rint = 0.026
21193 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.158H-atom parameters constrained
S = 1.09Δρmax = 0.38 e Å3
5070 reflectionsΔρmin = 0.26 e Å3
281 parameters
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 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).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.38293 (7)0.14318 (15)0.00934 (8)0.0871 (5)
O10.46981 (5)0.59709 (12)0.36061 (8)0.0510 (4)
O20.28907 (6)0.81844 (13)0.29527 (8)0.0559 (4)
O30.26165 (6)0.60434 (13)0.35157 (8)0.0541 (4)
O40.43779 (6)0.37861 (13)0.40222 (8)0.0528 (4)
C10.33939 (7)0.55677 (16)0.29460 (9)0.0374 (4)
C20.30171 (7)0.50860 (17)0.38325 (9)0.0410 (4)
C30.34468 (7)0.48284 (16)0.36326 (9)0.0374 (4)
C40.37305 (7)0.69315 (16)0.31271 (9)0.0394 (4)
C50.37392 (7)0.39250 (16)0.14693 (9)0.0397 (4)
C60.39243 (8)0.30729 (19)0.47009 (10)0.0478 (4)
C70.30055 (9)0.42833 (19)0.44439 (10)0.0490 (5)
C80.37200 (8)0.48601 (18)0.20228 (10)0.0435 (4)
C90.41934 (8)0.40838 (19)0.13113 (10)0.0468 (4)
C100.34759 (7)0.45888 (17)0.24304 (9)0.0401 (4)
C110.39165 (7)0.39240 (17)0.40863 (9)0.0412 (4)
C130.33133 (8)0.28989 (19)0.10782 (10)0.0492 (5)
C140.37988 (9)0.22567 (19)0.04230 (11)0.0533 (5)
C150.34225 (8)0.81682 (18)0.30644 (10)0.0449 (4)
C160.42251 (9)0.3253 (2)0.07889 (11)0.0541 (5)
C170.33405 (10)0.2057 (2)0.05524 (11)0.0567 (5)
C180.33098 (8)0.28697 (18)0.46091 (10)0.0467 (4)
C190.43444 (8)0.70204 (17)0.34034 (10)0.0446 (4)
C200.37073 (9)0.95534 (18)0.31481 (12)0.0566 (5)
C210.42333 (9)0.95511 (18)0.30305 (12)0.0533 (5)
C220.46479 (9)0.83836 (19)0.34999 (13)0.0596 (5)
C230.34063 (11)0.2288 (3)0.53606 (12)0.0654 (6)
C240.29292 (10)0.1860 (2)0.39620 (12)0.0598 (5)
C250.39917 (12)0.9295 (3)0.21754 (13)0.0734 (7)
C260.45606 (12)1.0926 (2)0.32438 (16)0.0802 (7)
H10.29690.58340.26400.0448*
H1A0.45450.53160.36950.0612*
H30.27300.66240.33290.0649*
H6A0.41900.35110.51900.0574*
H6B0.40920.21740.47110.0574*
H7A0.25900.41540.42980.0588*
H7B0.32020.48220.49100.0588*
H80.3906 (8)0.5785 (19)0.2057 (10)0.046 (5)*
H90.44820.47660.15640.0562*
H100.3290 (9)0.3665 (19)0.2366 (11)0.049 (5)*
H130.30040.27760.11710.0590*
H160.45310.33700.06880.0649*
H170.30540.13730.02940.0681*
H20A0.38440.99060.36550.0679*
H20B0.34041.01830.27830.0679*
H22A0.49500.82730.33650.0716*
H22B0.48540.86410.40350.0716*
H23A0.30300.22750.53390.0785*
H23B0.36870.28600.57780.0785*
H23C0.35620.13670.54350.0785*
H24A0.28820.22020.34950.0717*
H24B0.25410.17640.39040.0717*
H24C0.31250.09780.40800.0717*
H25A0.43210.92780.20930.0880*
H25B0.37191.00210.18770.0880*
H25C0.37850.84260.20250.0880*
H26A0.48551.09290.30980.0962*
H26B0.47571.10620.37850.0962*
H26C0.42771.16570.29830.0962*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.1116 (12)0.0874 (9)0.0818 (10)0.0026 (8)0.0642 (10)0.0334 (8)
O10.0345 (7)0.0479 (7)0.0673 (9)0.0074 (5)0.0243 (6)0.0042 (6)
O20.0429 (8)0.0621 (8)0.0646 (9)0.0186 (6)0.0295 (7)0.0060 (7)
O30.0441 (8)0.0627 (8)0.0656 (9)0.0137 (6)0.0357 (7)0.0085 (7)
O40.0414 (7)0.0620 (8)0.0626 (8)0.0166 (6)0.0325 (7)0.0123 (7)
C10.0297 (8)0.0471 (9)0.0356 (8)0.0065 (7)0.0173 (7)0.0019 (7)
C20.0348 (9)0.0497 (9)0.0396 (9)0.0011 (7)0.0203 (8)0.0048 (7)
C30.0312 (8)0.0470 (9)0.0341 (8)0.0038 (7)0.0171 (7)0.0012 (7)
C40.0359 (9)0.0440 (9)0.0370 (8)0.0066 (7)0.0183 (7)0.0001 (7)
C50.0425 (9)0.0425 (9)0.0376 (8)0.0010 (7)0.0233 (8)0.0030 (7)
C60.0443 (10)0.0582 (11)0.0366 (9)0.0051 (8)0.0182 (8)0.0064 (8)
C70.0500 (11)0.0617 (11)0.0465 (10)0.0002 (9)0.0330 (9)0.0037 (9)
C80.0456 (10)0.0447 (9)0.0456 (9)0.0018 (8)0.0276 (8)0.0010 (8)
C90.0423 (10)0.0523 (10)0.0505 (10)0.0049 (8)0.0276 (9)0.0040 (8)
C100.0388 (9)0.0448 (9)0.0378 (9)0.0026 (7)0.0208 (8)0.0008 (7)
C110.0345 (9)0.0502 (9)0.0381 (9)0.0016 (7)0.0184 (7)0.0021 (7)
C130.0482 (11)0.0565 (10)0.0516 (10)0.0086 (8)0.0322 (9)0.0017 (8)
C140.0636 (12)0.0534 (10)0.0486 (10)0.0056 (9)0.0334 (10)0.0074 (9)
C150.0422 (10)0.0504 (10)0.0409 (9)0.0109 (8)0.0208 (8)0.0018 (8)
C160.0505 (11)0.0637 (12)0.0612 (12)0.0023 (9)0.0383 (10)0.0039 (10)
C170.0617 (13)0.0527 (11)0.0549 (11)0.0141 (9)0.0301 (10)0.0109 (9)
C180.0495 (11)0.0544 (10)0.0400 (9)0.0027 (8)0.0260 (9)0.0006 (8)
C190.0395 (9)0.0458 (9)0.0466 (10)0.0051 (7)0.0213 (8)0.0018 (8)
C200.0600 (13)0.0452 (10)0.0633 (12)0.0092 (9)0.0314 (11)0.0039 (9)
C210.0591 (12)0.0418 (9)0.0634 (12)0.0028 (8)0.0350 (10)0.0007 (9)
C220.0457 (11)0.0515 (11)0.0734 (14)0.0025 (9)0.0254 (11)0.0042 (10)
C230.0763 (15)0.0750 (14)0.0540 (12)0.0025 (11)0.0405 (12)0.0084 (10)
C240.0588 (13)0.0620 (12)0.0555 (12)0.0088 (10)0.0279 (10)0.0063 (10)
C250.0962 (19)0.0677 (13)0.0680 (14)0.0037 (13)0.0512 (14)0.0025 (11)
C260.0828 (18)0.0496 (12)0.106 (2)0.0079 (11)0.0482 (16)0.0115 (13)
Geometric parameters (Å, º) top
F1—C141.365 (3)C21—C261.519 (3)
O1—C191.288 (2)O1—H1A0.820
O2—C151.284 (3)O3—H30.820
O3—C21.291 (2)C1—H10.980
O4—C111.286 (3)C6—H6A0.970
C1—C31.524 (3)C6—H6B0.970
C1—C41.522 (3)C7—H7A0.970
C1—C101.519 (3)C7—H7B0.970
C2—C31.405 (4)C8—H81.01 (2)
C2—C71.492 (3)C9—H90.930
C3—C111.395 (2)C10—H100.993 (19)
C4—C151.412 (3)C13—H130.930
C4—C191.395 (3)C16—H160.930
C5—C81.476 (3)C17—H170.930
C5—C91.393 (4)C20—H20A0.970
C5—C131.392 (3)C20—H20B0.970
C6—C111.501 (3)C22—H22A0.970
C6—C181.527 (4)C22—H22B0.970
C7—C181.531 (3)C23—H23A0.960
C8—C101.318 (4)C23—H23B0.960
C9—C161.379 (4)C23—H23C0.960
C13—C171.386 (4)C24—H24A0.960
C14—C161.364 (3)C24—H24B0.960
C14—C171.369 (4)C24—H24C0.960
C15—C201.501 (3)C25—H25A0.960
C18—C231.537 (4)C25—H25B0.960
C18—C241.527 (3)C25—H25C0.960
C19—C221.500 (3)C26—H26A0.960
C20—C211.514 (4)C26—H26B0.960
C21—C221.513 (3)C26—H26C0.960
C21—C251.546 (4)
O1···O42.582 (2)H25A···H26C2.9839
O1···C12.958 (2)H25B···H26A2.8412
O1···C33.478 (3)H25B···H26B3.5526
O1···C83.094 (2)H25B···H26C2.5181
O1···C103.1214 (18)H25C···H26A3.4790
O1···C113.345 (3)H25C···H26C3.5627
O2···O32.652 (3)F1···H3i3.5443
O2···C12.861 (3)F1···H20Ai2.8996
O2···C23.432 (3)F1···H23Cxi3.1345
O2···C33.539 (2)F1···H24Cxi2.9076
O2···C193.586 (3)F1···H26Bviii3.2540
O3···C12.863 (3)O1···H6Aii2.6989
O3···C43.504 (3)O1···H9iii2.6183
O3···C113.599 (3)O1···H16iii3.0762
O3···C153.403 (3)O2···H1v3.2037
O4···C12.9201 (19)O2···H10v2.84 (3)
O4···C23.594 (3)O2···H24Av2.7478
O4···C43.505 (2)O2···H24Cix3.4056
O4···C102.9649 (19)O3···H10v3.295 (18)
O4···C193.368 (3)O3···H13v2.6374
C2···C43.407 (3)O3···H20Bvii2.7334
C2···C62.860 (3)O3···H25Bvii3.2933
C2···C243.158 (3)O4···H16iii2.6202
C3···C153.432 (3)O4···H26Bvi2.9496
C3···C182.919 (3)O4···H26Cvi2.8821
C3···C193.375 (3)C1···H24Av3.4711
C3···C243.396 (3)C1···H24Bv3.4705
C4···C83.021 (3)C2···H20Bvii3.4491
C4···C113.410 (3)C5···H7Bi3.0013
C4···C212.913 (3)C5···H23Bi3.3995
C4···C253.308 (4)C5···H26Cvi3.4528
C5···C142.761 (3)C6···H22Bii3.3179
C7···C112.856 (4)C7···H23Axii3.3259
C8···C193.203 (3)C8···H23Bi3.3493
C9···C172.760 (3)C8···H24Bv3.3632
C10···C113.038 (3)C8···H26Cvi3.5574
C10···C133.059 (3)C9···H1Aiii3.5108
C10···C193.155 (3)C9···H6Ai3.2768
C11···C243.167 (4)C9···H7Bi2.8835
C13···C162.761 (4)C9···H23Bi3.1961
C15···C222.843 (4)C10···H24Bv3.3756
C15···C253.097 (5)C10···H26Cvi3.3555
C19···C202.857 (3)C13···H7Bi3.1625
C19···C253.107 (3)C13···H17xiii3.2645
F1···O2i3.4600 (19)C13···H25Bvi3.1280
F1···C15i3.378 (3)C13···H26Cvi3.5780
F1···C20i3.589 (4)C14···H7Bi3.1374
O1···C6ii3.5777 (18)C14···H23Cxi3.5700
O1···C9iii3.353 (3)C14···H26Aviii3.4741
O1···C16iii3.569 (3)C14···H26Bviii3.4324
O2···F1iv3.4600 (19)C15···H24Av3.3645
O2···C10v3.502 (3)C16···H1Aiii3.4456
O2···C24v3.592 (3)C16···H6Ai3.3549
O3···C13v3.458 (3)C16···H7Bi2.9717
O4···C16iii3.499 (3)C16···H26Aviii3.2142
O4···C26vi3.358 (4)C16···H26Bviii3.1474
C6···O1ii3.5777 (18)C17···H7Bi3.2451
C9···O1iii3.353 (3)C17···H13xiii3.4469
C10···O2vii3.502 (3)C17···H17xiii3.4602
C13···O3vii3.458 (3)C17···H23Cxi3.4005
C15···F1iv3.378 (3)C17···H25Bvi3.0778
C16···O1iii3.569 (3)C18···H23Axii3.5590
C16···O4iii3.499 (3)C19···H6Aii3.4183
C16···C26viii3.535 (3)C20···H24Cix3.3082
C20···F1iv3.589 (4)C22···H6Aii3.3583
C23···C25iv3.556 (4)C22···H6Bii3.4608
C24···O2vii3.592 (3)C22···H25Aiii3.5958
C25···C23i3.556 (4)C23···H7Axii3.3374
C26···O4ix3.358 (4)C23···H8iv3.55 (2)
C26···C16x3.535 (3)C23···H23Axii3.2657
F1···H162.5265C23···H25Aiv3.4340
F1···H172.5341C23···H25Biv3.5689
O1···H82.749 (17)C23···H25Civ3.1025
O1···H22A2.4503C24···H1vii3.0411
O1···H22B2.6959C24···H20Avi3.3570
O2···H12.4058C24···H23Axii3.5806
O2···H31.8447C25···H23Ai3.5987
O2···H20A2.7014C25···H23Bi3.2955
O2···H20B2.4821C25···H23Ci3.2059
O3···H12.4234C26···H16x3.2570
O3···H7A2.4622H1···O2vii3.2037
O3···H7B2.7150H1···C24v3.0411
O4···H1A1.7755H1···H20Bvii3.2784
O4···H6A2.7041H1···H24Av2.5911
O4···H6B2.4732H1···H24Bv2.8692
O4···H103.090 (16)H1···H24Cv3.1795
C1···H1A2.5724H1A···C9iii3.5108
C1···H32.4700H1A···C16iii3.4456
C1···H82.78 (3)H1A···H6Aii3.0874
C2···H12.4971H1A···H9iii2.9050
C2···H6A3.2475H1A···H16iii2.7913
C2···H24A2.8580H3···F1iv3.5443
C2···H24B3.4831H3···H10v3.0122
C3···H1A2.8426H3···H13v2.8370
C3···H32.3869H3···H20Bvii2.9758
C3···H6A3.0234H3···H24Av3.2648
C3···H6B3.2346H6A···O1ii2.6989
C3···H7A3.2415H6A···C9iv3.2768
C3···H7B3.0127H6A···C16iv3.3549
C3···H102.67 (3)H6A···C19ii3.4183
C3···H24A2.8821H6A···C22ii3.3583
C4···H1A2.3956H6A···H1Aii3.0874
C4···H32.8668H6A···H9iv3.0169
C4···H82.71 (3)H6A···H16iv3.1682
C4···H103.452 (18)H6A···H22Aii3.1425
C4···H20A3.0406H6A···H22Bii2.9929
C4···H20B3.2454H6B···C22ii3.4608
C4···H22A3.2316H6B···H20Avi2.9153
C4···H22B3.0167H6B···H22Aii3.4254
C4···H25C2.7559H6B···H22Bii2.7239
C5···H102.66 (3)H6B···H26Bvi3.3576
C5···H163.2585H7A···C23xii3.3374
C5···H173.2614H7A···H17v3.1063
C6···H7A3.3010H7A···H23Axii2.5240
C6···H7B2.7340H7A···H23Cxii3.3690
C6···H23A3.3140H7A···H25Bvii3.0946
C6···H23B2.6019H7A···H25Cvii3.2487
C6···H23C2.7206H7B···C5iv3.0013
C6···H24A2.6832H7B···C9iv2.8835
C6···H24B3.3376H7B···C13iv3.1625
C6···H24C2.7056H7B···C14iv3.1374
C7···H33.0328H7B···C16iv2.9717
C7···H6A2.7402H7B···C17iv3.2451
C7···H6B3.3008H7B···H9iv3.3151
C7···H23A2.6568H7B···H16iv3.4437
C7···H23B2.7355H7B···H17v3.4281
C7···H23C3.3399H8···C23i3.55 (2)
C7···H24A2.7057H8···H23Ai3.5752
C7···H24B2.6945H8···H23Bi2.7186
C7···H24C3.3429H8···H24Bv3.3563
C8···H12.9917H9···O1iii2.6183
C8···H1A2.9829H9···H1Aiii2.9050
C8···H92.6130H9···H6Ai3.0169
C8···H132.6860H9···H7Bi3.3151
C8···H25C3.4618H9···H9iii3.3508
C9···H82.62 (3)H9···H23Bi2.9511
C9···H133.2248H10···O2vii2.84 (3)
C10···H1A2.7289H10···O3vii3.295 (18)
C10···H132.8230H10···H3vii3.0122
C11···H13.2688H10···H20Bvi3.4585
C11···H1A2.5590H10···H26Cvi2.9353
C11···H7B3.2294H13···O3vii2.6374
C11···H103.03 (2)H13···C17xiii3.4469
C11···H24A2.8507H13···H3vii2.8370
C11···H24C3.5218H13···H17xiii2.9453
C13···H83.319 (18)H13···H25Bvi3.1443
C13···H93.2243H16···O1iii3.0762
C13···H102.78 (3)H16···O4iii2.6202
C14···H93.1969H16···C26viii3.2570
C14···H133.2053H16···H1Aiii2.7913
C15···H12.4902H16···H6Ai3.1682
C15···H32.6145H16···H7Bi3.4437
C15···H22B3.2173H16···H26Aviii3.1956
C15···H25B3.4305H16···H26Bviii2.7439
C15···H25C2.7652H16···H26Cviii3.3177
C16···H173.2322H17···C13xiii3.2645
C17···H163.2321H17···C17xiii3.4602
C19···H13.2823H17···H7Avii3.1063
C19···H82.663 (19)H17···H7Bvii3.4281
C19···H20A3.2423H17···H13xiii2.9453
C19···H25A3.4469H17···H17xiii3.3099
C19···H25C2.7731H17···H23Axi3.5394
C20···H22A3.2797H17···H23Cxi2.9151
C20···H22B2.7119H17···H24Cxi3.4557
C20···H25A3.3149H17···H25Bvi3.0675
C20···H25B2.6686H20A···F1iv2.8996
C20···H25C2.6571H20A···C24ix3.3570
C20···H26A3.3304H20A···H6Bix2.9153
C20···H26B2.7584H20A···H24Aix3.2422
C20···H26C2.6485H20A···H24Cix2.6614
C22···H1A3.0318H20B···O3v2.7334
C22···H83.590 (18)H20B···C2v3.4491
C22···H20A2.7190H20B···H1v3.2784
C22···H20B3.2793H20B···H3v2.9758
C22···H25A2.6944H20B···H10ix3.4585
C22···H25B3.3258H20B···H24Aix3.1516
C22···H25C2.6684H20B···H24Cix3.2052
C22···H26A2.7448H22A···H6Aii3.1425
C22···H26B2.6447H22A···H6Bii3.4254
C22···H26C3.3257H22A···H23Bii3.2262
C23···H6A2.5432H22A···H23Cii3.3559
C23···H6B2.7395H22A···H25Aiii2.7089
C23···H7A2.7768H22B···C6ii3.3179
C23···H7B2.5806H22B···H6Aii2.9929
C23···H24A3.3302H22B···H6Bii2.7239
C23···H24B2.6919H23A···C7xii3.3259
C23···H24C2.6575H23A···C18xii3.5590
C24···H6A3.3266H23A···C23xii3.2657
C24···H6B2.6039H23A···C24xii3.5806
C24···H7A2.6170H23A···C25iv3.5987
C24···H7B3.3328H23A···H7Axii2.5240
C24···H23A2.7323H23A···H8iv3.5752
C24···H23B3.3254H23A···H17xiv3.5394
C24···H23C2.6241H23A···H23Axii2.3987
C25···H83.411 (19)H23A···H24Bxii2.8208
C25···H20A3.3152H23A···H25Biv3.4980
C25···H20B2.5823H23A···H25Civ3.0346
C25···H22A2.6105H23B···C5iv3.3995
C25···H22B3.3273H23B···C8iv3.3493
C25···H26A2.5899H23B···C9iv3.1961
C25···H26B3.3102H23B···C25iv3.2955
C25···H26C2.6949H23B···H8iv2.7186
C26···H20A2.6190H23B···H9iv2.9511
C26···H20B2.7469H23B···H22Aii3.2262
C26···H22A2.7291H23B···H25Aiv3.1085
C26···H22B2.6149H23B···H25Biv3.5664
C26···H25A2.6442H23B···H25Civ2.7403
C26···H25B2.6512H23C···F1xiv3.1345
C26···H25C3.3080H23C···C14xiv3.5700
H1···H1A3.5404H23C···C17xiv3.4005
H1···H31.9773H23C···C25iv3.2059
H1···H83.2400H23C···H7Axii3.3690
H1···H102.4367H23C···H17xiv2.9151
H1A···H82.9071H23C···H22Aii3.3559
H1A···H103.3743H23C···H25Aiv2.9786
H1A···H22A3.2484H23C···H25Biv3.0829
H1A···H22B3.3076H23C···H25Civ3.0132
H3···H7A3.2561H24A···O2vii2.7478
H3···H7B3.3091H24A···C1vii3.4711
H6A···H7B2.6557H24A···C15vii3.3645
H6A···H23A3.4169H24A···H1vii2.5911
H6A···H23B2.2912H24A···H3vii3.2648
H6A···H23C2.8504H24A···H20Avi3.2422
H6A···H24A3.5984H24A···H20Bvi3.1516
H6A···H24C3.5100H24B···C1vii3.4705
H6B···H23B2.9667H24B···C8vii3.3632
H6B···H23C2.6258H24B···C10vii3.3756
H6B···H24A2.8206H24B···H1vii2.8692
H6B···H24B3.5017H24B···H8vii3.3563
H6B···H24C2.4427H24B···H23Axii2.8208
H7A···H23A2.5778H24B···H25Cvii3.3627
H7A···H23B3.1479H24C···F1xiv2.9076
H7A···H24A2.8632H24C···O2vi3.4056
H7A···H24B2.4360H24C···C20vi3.3082
H7A···H24C3.5057H24C···H1vii3.1795
H7B···H23A2.7369H24C···H17xiv3.4557
H7B···H23B2.4577H24C···H20Avi2.6614
H7B···H23C3.4938H24C···H20Bvi3.2052
H7B···H24B3.5089H25A···C22iii3.5958
H8···H92.4215H25A···C23i3.4340
H8···H102.88 (4)H25A···H22Aiii2.7089
H8···H133.5893H25A···H23Bi3.1085
H8···H22A3.5787H25A···H23Ci2.9786
H8···H25A3.5445H25A···H25Aiii3.0256
H8···H25C2.5769H25A···H26Aiii2.8698
H9···H162.3086H25B···O3v3.2933
H10···H132.3260H25B···C13ix3.1280
H10···H24A3.3387H25B···C17ix3.0778
H13···H172.3178H25B···C23i3.5689
H20A···H22B2.6301H25B···H7Av3.0946
H20A···H25B3.4985H25B···H13ix3.1443
H20A···H25C3.5747H25B···H17ix3.0675
H20A···H26A3.5269H25B···H23Ai3.4980
H20A···H26B2.5201H25B···H23Bi3.5664
H20A···H26C2.7765H25B···H23Ci3.0829
H20B···H25A3.4755H25C···C23i3.1025
H20B···H25B2.4038H25C···H7Av3.2487
H20B···H25C2.8185H25C···H23Ai3.0346
H20B···H26A3.5677H25C···H23Bi2.7403
H20B···H26B3.1360H25C···H23Ci3.0132
H20B···H26C2.5353H25C···H24Bv3.3627
H22A···H25A2.4463H26A···C14x3.4741
H22A···H25B3.5021H26A···C16x3.2142
H22A···H25C2.8446H26A···H16x3.1956
H22A···H26A2.6175H26A···H25Aiii2.8698
H22A···H26B2.9612H26A···H26Aiii2.9284
H22B···H25A3.5263H26B···F1x3.2540
H22B···H25C3.5821H26B···O4ix2.9496
H22B···H26A2.9391H26B···C14x3.4324
H22B···H26B2.3881H26B···C16x3.1474
H22B···H26C3.4761H26B···H6Bix3.3576
H23A···H24B2.5761H26B···H16x2.7439
H23A···H24C3.0027H26C···O4ix2.8821
H23B···H24B3.5851H26C···C5ix3.4528
H23B···H24C3.5078H26C···C8ix3.5574
H23C···H24A3.5058H26C···C10ix3.3555
H23C···H24B2.8935H26C···C13ix3.5780
H23C···H24C2.4234H26C···H10ix2.9353
H25A···H26A2.3988H26C···H16x3.3177
H25A···H26B3.4989
C3—C1—C4114.93 (13)C11—C6—H6B108.604
C3—C1—C10112.04 (14)C18—C6—H6A108.596
C4—C1—C10116.04 (18)C18—C6—H6B108.601
O3—C2—C3122.72 (19)H6A—C6—H6B107.561
O3—C2—C7115.6 (2)C2—C7—H7A108.609
C3—C2—C7121.71 (15)C2—C7—H7B108.601
C1—C3—C2119.27 (14)C18—C7—H7A108.608
C1—C3—C11122.46 (19)C18—C7—H7B108.602
C2—C3—C11118.26 (18)H7A—C7—H7B107.579
C1—C4—C15119.16 (16)C5—C8—H8113.0 (15)
C1—C4—C19123.12 (15)C10—C8—H8120.8 (15)
C15—C4—C19117.58 (15)C5—C9—H9119.245
C8—C5—C9119.27 (15)C16—C9—H9119.224
C8—C5—C13123.0 (2)C1—C10—H10114.8 (16)
C9—C5—C13117.69 (19)C8—C10—H10117.3 (15)
C11—C6—C18114.65 (14)C5—C13—H13119.337
C2—C7—C18114.6 (2)C17—C13—H13119.338
C5—C8—C10126.20 (17)C9—C16—H16120.715
C5—C9—C16121.53 (17)C14—C16—H16120.700
C1—C10—C8127.65 (16)C13—C17—H17120.792
O4—C11—C3122.67 (19)C14—C17—H17120.814
O4—C11—C6115.41 (15)C15—C20—H20A108.602
C3—C11—C6121.9 (2)C15—C20—H20B108.605
C5—C13—C17121.3 (3)C21—C20—H20A108.614
F1—C14—C16118.7 (3)C21—C20—H20B108.604
F1—C14—C17118.79 (17)H20A—C20—H20B107.564
C16—C14—C17122.5 (3)C19—C22—H22A108.521
O2—C15—C4122.55 (17)C19—C22—H22B108.501
O2—C15—C20115.74 (17)C21—C22—H22A108.517
C4—C15—C20121.69 (19)C21—C22—H22B108.512
C9—C16—C14118.6 (3)H22A—C22—H22B107.534
C13—C17—C14118.39 (19)C18—C23—H23A109.468
C6—C18—C7107.56 (17)C18—C23—H23B109.479
C6—C18—C23108.35 (15)C18—C23—H23C109.468
C6—C18—C24110.6 (2)H23A—C23—H23B109.472
C7—C18—C23110.1 (2)H23A—C23—H23C109.462
C7—C18—C24110.84 (13)H23B—C23—H23C109.478
C23—C18—C24109.27 (18)C18—C24—H24A109.473
O1—C19—C4124.01 (16)C18—C24—H24B109.467
O1—C19—C22114.44 (17)C18—C24—H24C109.473
C4—C19—C22121.55 (16)H24A—C24—H24B109.461
C15—C20—C21114.63 (18)H24A—C24—H24C109.482
C20—C21—C22107.8 (2)H24B—C24—H24C109.472
C20—C21—C25108.55 (18)C21—C25—H25A109.474
C20—C21—C26111.9 (2)C21—C25—H25B109.462
C22—C21—C25109.5 (2)C21—C25—H25C109.465
C22—C21—C26111.47 (16)H25A—C25—H25B109.488
C25—C21—C26107.6 (3)H25A—C25—H25C109.479
C19—C22—C21115.02 (16)H25B—C25—H25C109.459
C19—O1—H1A109.456C21—C26—H26A109.470
C2—O3—H3109.461C21—C26—H26B109.469
C3—C1—H1104.006C21—C26—H26C109.472
C4—C1—H1104.005H26A—C26—H26B109.472
C10—C1—H1104.004H26A—C26—H26C109.471
C11—C6—H6A108.608H26B—C26—H26C109.473
C3—C1—C4—C1593.59 (17)C8—C5—C13—C17178.82 (13)
C3—C1—C4—C1982.0 (3)C13—C5—C8—C1026.9 (3)
C4—C1—C3—C291.11 (17)C9—C5—C13—C170.4 (3)
C4—C1—C3—C1187.27 (19)C13—C5—C9—C160.3 (3)
C3—C1—C10—C8146.85 (13)C11—C6—C18—C747.8 (2)
C10—C1—C3—C2133.63 (14)C11—C6—C18—C23166.88 (14)
C10—C1—C3—C1148.00 (18)C11—C6—C18—C2473.35 (18)
C4—C1—C10—C812.11 (19)C18—C6—C11—O4160.81 (14)
C10—C1—C4—C15132.97 (15)C18—C6—C11—C320.9 (3)
C10—C1—C4—C1951.4 (2)C2—C7—C18—C648.65 (17)
O3—C2—C3—C18.3 (2)C2—C7—C18—C23166.54 (12)
O3—C2—C3—C11170.12 (12)C2—C7—C18—C2472.4 (2)
O3—C2—C7—C18158.96 (13)C5—C8—C10—C1173.56 (12)
C3—C2—C7—C1822.5 (2)C5—C9—C16—C140.0 (3)
C7—C2—C3—C1173.21 (12)C5—C13—C17—C140.1 (3)
C7—C2—C3—C118.3 (2)F1—C14—C16—C9179.91 (14)
C1—C3—C11—O49.4 (3)F1—C14—C17—C13179.96 (14)
C1—C3—C11—C6172.44 (12)C16—C14—C17—C130.3 (3)
C2—C3—C11—O4169.00 (13)C17—C14—C16—C90.3 (3)
C2—C3—C11—C69.2 (2)O2—C15—C20—C21161.68 (15)
C1—C4—C15—O28.9 (3)C4—C15—C20—C2120.0 (3)
C1—C4—C15—C20172.97 (15)O1—C19—C22—C21159.85 (19)
C1—C4—C19—O17.4 (4)C4—C19—C22—C2121.1 (4)
C1—C4—C19—C22173.69 (16)C15—C20—C21—C2248.2 (2)
C15—C4—C19—O1168.26 (18)C15—C20—C21—C2570.38 (18)
C15—C4—C19—C2210.7 (3)C15—C20—C21—C26171.05 (14)
C19—C4—C15—O2166.96 (17)C20—C21—C22—C1948.9 (3)
C19—C4—C15—C2011.2 (3)C25—C21—C22—C1969.0 (3)
C8—C5—C9—C16178.84 (13)C26—C21—C22—C19172.0 (3)
C9—C5—C8—C10154.65 (15)
Symmetry codes: (i) x, y+1, z1/2; (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, y1, z; (vii) x+1/2, y1/2, z+1/2; (viii) x+1, y1, z+1/2; (ix) x, y+1, z; (x) x+1, y+1, z+1/2; (xi) x, y, z1/2; (xii) x+1/2, y+1/2, z+1; (xiii) x+1/2, y+1/2, z; (xiv) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O40.821.782.582 (2)168
O3—H3···O20.821.852.652 (3)168
C9—H9···O1iii0.932.623.353 (3)136
C16—H16···O4iii0.932.623.499 (3)158
Symmetry code: (iii) x+1, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC25H29FO4
Mr412.50
Crystal system, space groupMonoclinic, C2/c
Temperature (K)296
a, b, c (Å)26.1146 (13), 9.6961 (4), 20.5638 (9)
β (°) 121.5921 (15)
V3)4435.3 (4)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Rigaku, 1995)
Tmin, Tmax0.771, 0.991
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
21193, 5070, 3370
Rint0.026
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.158, 1.09
No. of reflections5070
No. of parameters281
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.26

Computer programs: RAPID-AUTO (Rigaku, 2006), Il Milione (Burla et al., 2007), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O40.821.782.582 (2)168
O3—H3···O20.821.852.652 (3)168
C9—H9···O1i0.932.623.353 (3)136
C16—H16···O4i0.932.623.499 (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

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