supplementary materials


ff2106 scheme

Acta Cryst. (2013). E69, o985    [ doi:10.1107/S1600536813014049 ]

(E)-9-(4-Fluorostyryl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione

J. K. Lee, S.-J. Min, Y. S. Cho, J. H. Cha and S. O. Won

Abstract top

In the title compound, C25H27FO3, each of the cyclohexenone rings adopts a half-chair conformation, whereas the six-membered pyran ring adopts a flattened boat conformation, with the O and methine C atoms deviating by 0.0769 (15) and 0.196 (2) Å, respectively, from the plane of the other four atoms (r.m.s. deviation = 0.004 Å). The C=C double bond adopts an E conformation. The dihedral angle between the benzene and pyran (all atoms) rings is 89.94 (10)°. In the crystal, weak C-H...O hydrogen bonds link the molecules into chains running parallel to the b axis.

Comment top

As part of our ongoing study of the substituent effect on the solid state structures of xanthene derivatives (Cha et al., 2012; Lee et al., 2012), we present here the crystal structure of the title compound (I) (Fig. 1).

The starting material, (E)-2.2-(3-(4-Fluorophenyl)prop-2-ene-1,1-diyl) bis(3-hydroxy-5,5-δimethylcyclohex-2-enone) was prepared according to the reported method (Cha et al., 2013). In (I) (Fig. 1), the bond lengths and angles are normal and correspond to those observed in related structures (Cha et al., 2013). The dihedral angle between the benzene ring (C16 - C21) system and the pyran ring (C1—C2—C7—O3—C8—C13) is 89.94 (10)°. The C14=C15 double bond has an E conformation. All two cyclohexenone rings in (Fig. 1) display half-chair conformation, whereas the pyran ring adopts a boat conformation.

In the crystal, weak intermolecular C—H···O hydrogen bonds link molecules into chains running parallel to the b axis.

Related literature top

For the crystal structures of xanthenes derivatives studied recently by our group, see: Cha et al. (2012, 2013); Lee et al. (2012).

Experimental top

To solution of (E)-2.2-(3-(4-Fluorophenyl)prop-2-ene-1,1-diyl)bis (3-hydroxy-5,5-dimethylcyclohex-2-enone) (1.25 mmol) was added methanol and catalytic amounts of sulfuric acid in under nitrogen atmosphere. After stirring for 4 h, the progress of reaction was monitored by TLC. The solvent was evaporated and the remaining residue dissolved in ethyl acetate. The mixture was neutralized with saturated sodium bicarbonate and the solution was extracted with ethyl acetate. The resulting residue solid was purified by recrystallization from ethanol and methylene chloride to afford yield 91%) colourless block type crystals suitable for X-ray analysis.

Refinement top

All hydrogen atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.98 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, 1995); data reduction: RAPID-AUTO (Rigaku, 1995); 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)-9-(4-Fluorostyryl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione top
Crystal data top
C25H27FO3F(000) = 840.00
Mr = 394.48Dx = 1.226 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybcCell parameters from 12751 reflections
a = 5.9367 (7) Åθ = 3.0–27.5°
b = 18.8521 (16) ŵ = 0.09 mm1
c = 19.3709 (16) ÅT = 296 K
β = 99.681 (3)°Chunk, colourless
V = 2137.1 (4) Å30.30 × 0.20 × 0.20 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2857 reflections with F2 > 2σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.037
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
h = 77
Tmin = 0.773, Tmax = 0.983k = 2424
20480 measured reflectionsl = 2225
4864 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0774P)2 + 0.3562P]
where P = (Fo2 + 2Fc2)/3
4864 reflections(Δ/σ)max < 0.001
274 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = 0.24 e Å3
Primary atom site location: structure-invariant direct methods
Crystal data top
C25H27FO3V = 2137.1 (4) Å3
Mr = 394.48Z = 4
Monoclinic, P21/cMo Kα radiation
a = 5.9367 (7) ŵ = 0.09 mm1
b = 18.8521 (16) ÅT = 296 K
c = 19.3709 (16) Å0.30 × 0.20 × 0.20 mm
β = 99.681 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4864 independent reflections
Absorption correction: multi-scan
(ABSCOR; Rigaku, 1995)
2857 reflections with F2 > 2σ(F2)
Tmin = 0.773, Tmax = 0.983Rint = 0.037
20480 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.169Δρmax = 0.42 e Å3
S = 1.09Δρmin = 0.24 e Å3
4864 reflectionsAbsolute structure: ?
274 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
F11.3085 (4)0.41875 (10)0.55088 (8)0.1071 (7)
O10.3415 (3)0.16938 (9)0.26856 (10)0.0755 (6)
O20.5001 (4)0.40605 (8)0.14354 (9)0.0743 (6)
O30.9010 (3)0.19315 (7)0.12327 (7)0.0508 (4)
C10.5863 (4)0.26673 (10)0.19791 (9)0.0457 (5)
C20.6201 (4)0.18746 (10)0.19814 (9)0.0427 (5)
C30.4790 (4)0.14307 (12)0.23554 (11)0.0541 (6)
C40.5029 (4)0.06354 (12)0.22949 (12)0.0591 (6)
C50.7461 (4)0.03924 (10)0.22594 (10)0.0451 (5)
C60.8316 (4)0.07994 (10)0.16669 (10)0.0484 (5)
C70.7745 (4)0.15633 (10)0.16515 (9)0.0424 (5)
C80.8474 (4)0.26351 (10)0.10936 (9)0.0449 (5)
C90.9782 (4)0.29226 (11)0.05617 (10)0.0517 (5)
C100.8696 (4)0.35891 (10)0.01931 (9)0.0469 (5)
C110.7974 (5)0.40786 (11)0.07479 (11)0.0592 (6)
C120.6512 (4)0.37327 (10)0.12129 (10)0.0512 (6)
C130.6981 (4)0.29901 (10)0.14075 (9)0.0445 (5)
C140.6839 (4)0.30007 (11)0.26838 (10)0.0487 (5)
C150.8830 (4)0.28526 (11)0.30532 (11)0.0501 (5)
C160.9898 (4)0.31916 (10)0.37108 (10)0.0454 (5)
C171.2137 (4)0.30241 (11)0.40059 (11)0.0542 (6)
C181.3216 (5)0.33576 (13)0.46122 (12)0.0635 (6)
C191.2036 (5)0.38498 (13)0.49183 (12)0.0671 (7)
C200.9810 (5)0.40299 (12)0.46566 (12)0.0638 (7)
C210.8770 (4)0.36963 (11)0.40537 (11)0.0539 (6)
C220.7571 (6)0.03946 (12)0.21348 (15)0.0782 (8)
C230.8977 (5)0.05692 (13)0.29641 (11)0.0641 (7)
C241.0446 (5)0.39614 (12)0.01757 (12)0.0632 (7)
C250.6614 (5)0.33915 (13)0.03464 (11)0.0621 (6)
H10.42210.27670.18760.0549*
H4A0.40230.04740.18770.0710*
H4B0.45330.04130.26950.0710*
H6A0.99610.07470.17200.0581*
H6B0.76520.05890.12220.0581*
H9A0.98850.25600.02130.0620*
H9B1.13230.30340.07900.0620*
H11A0.93390.42640.10380.0711*
H11B0.71440.44780.05130.0711*
H171.29250.26830.37940.0651*
H181.47160.32460.48040.0762*
H200.90330.43650.48790.0766*
H210.72660.38120.38690.0646*
H22A0.66990.05080.16850.0938*
H22B0.69510.06430.24930.0938*
H22C0.91330.05340.21480.0938*
H23A0.84030.03280.33350.0769*
H23B0.89580.10720.30430.0769*
H23C1.05150.04180.29540.0769*
H24A0.97760.43810.04050.0758*
H24B1.09080.36470.05160.0758*
H24C1.17560.40900.01630.0758*
H25A0.55170.31520.01180.0745*
H25B0.70740.30840.06930.0745*
H25C0.59400.38140.05680.0745*
H140.606 (5)0.3358 (14)0.2853 (13)0.080 (8)*
H150.976 (5)0.2514 (13)0.2866 (13)0.070 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.1157 (15)0.1169 (14)0.0759 (10)0.0103 (11)0.0212 (10)0.0327 (10)
O10.0723 (12)0.0670 (11)0.1011 (13)0.0029 (9)0.0546 (11)0.0011 (9)
O20.1033 (15)0.0543 (10)0.0726 (11)0.0236 (9)0.0359 (10)0.0042 (8)
O30.0574 (9)0.0486 (8)0.0522 (8)0.0101 (7)0.0257 (7)0.0112 (7)
C10.0488 (13)0.0489 (11)0.0410 (10)0.0065 (9)0.0121 (9)0.0005 (9)
C20.0447 (12)0.0447 (11)0.0398 (10)0.0003 (9)0.0109 (8)0.0013 (8)
C30.0488 (13)0.0572 (13)0.0605 (13)0.0001 (10)0.0210 (11)0.0010 (10)
C40.0537 (14)0.0595 (14)0.0660 (14)0.0074 (11)0.0149 (11)0.0005 (11)
C50.0478 (12)0.0414 (10)0.0488 (11)0.0023 (9)0.0157 (9)0.0013 (9)
C60.0528 (13)0.0471 (11)0.0486 (11)0.0026 (9)0.0183 (10)0.0003 (9)
C70.0451 (12)0.0461 (11)0.0380 (9)0.0001 (9)0.0128 (8)0.0019 (8)
C80.0515 (13)0.0440 (11)0.0394 (10)0.0016 (9)0.0084 (9)0.0041 (8)
C90.0548 (13)0.0534 (12)0.0495 (11)0.0022 (10)0.0162 (10)0.0080 (10)
C100.0560 (13)0.0445 (11)0.0399 (10)0.0030 (9)0.0073 (9)0.0033 (9)
C110.0814 (18)0.0426 (11)0.0550 (12)0.0065 (11)0.0153 (12)0.0009 (10)
C120.0691 (15)0.0439 (11)0.0413 (10)0.0030 (10)0.0112 (10)0.0063 (9)
C130.0527 (13)0.0450 (10)0.0364 (9)0.0026 (9)0.0100 (9)0.0000 (8)
C140.0591 (14)0.0477 (11)0.0412 (10)0.0116 (10)0.0143 (10)0.0020 (9)
C150.0520 (14)0.0481 (12)0.0519 (12)0.0063 (10)0.0133 (10)0.0070 (10)
C160.0503 (13)0.0432 (10)0.0444 (10)0.0008 (9)0.0124 (9)0.0033 (9)
C170.0538 (14)0.0541 (12)0.0558 (12)0.0031 (10)0.0121 (10)0.0050 (10)
C180.0553 (15)0.0706 (15)0.0611 (14)0.0025 (12)0.0000 (11)0.0090 (12)
C190.0787 (19)0.0662 (15)0.0524 (13)0.0144 (14)0.0006 (12)0.0048 (12)
C200.0752 (18)0.0623 (14)0.0541 (12)0.0026 (12)0.0113 (12)0.0123 (11)
C210.0537 (14)0.0561 (13)0.0521 (12)0.0046 (10)0.0098 (10)0.0038 (10)
C220.100 (3)0.0492 (13)0.0961 (19)0.0046 (13)0.0465 (17)0.0001 (13)
C230.0675 (17)0.0670 (15)0.0568 (13)0.0014 (12)0.0076 (12)0.0103 (12)
C240.0704 (17)0.0602 (14)0.0603 (13)0.0066 (12)0.0152 (12)0.0136 (11)
C250.0646 (16)0.0717 (15)0.0486 (12)0.0028 (12)0.0057 (11)0.0026 (11)
Geometric parameters (Å, º) top
F1—C191.365 (3)C19—C201.376 (4)
O1—C31.224 (3)C20—C211.378 (3)
O2—C121.226 (3)C1—H10.980
O3—C71.382 (3)C4—H4A0.970
O3—C81.380 (3)C4—H4B0.970
C1—C21.508 (3)C6—H6A0.970
C1—C131.511 (3)C6—H6B0.970
C1—C141.526 (3)C9—H9A0.970
C2—C31.460 (3)C9—H9B0.970
C2—C71.338 (3)C11—H11A0.970
C3—C41.512 (4)C11—H11B0.970
C4—C51.527 (4)C14—H140.91 (3)
C5—C61.536 (3)C15—H150.95 (3)
C5—C221.506 (3)C17—H170.930
C5—C231.540 (3)C18—H180.930
C6—C71.479 (3)C20—H200.930
C8—C91.492 (3)C21—H210.930
C8—C131.336 (3)C22—H22A0.960
C9—C101.533 (3)C22—H22B0.960
C10—C111.531 (3)C22—H22C0.960
C10—C241.527 (4)C23—H23A0.960
C10—C251.524 (3)C23—H23B0.960
C11—C121.501 (4)C23—H23C0.960
C12—C131.464 (3)C24—H24A0.960
C14—C151.305 (3)C24—H24B0.960
C15—C161.470 (3)C24—H24C0.960
C16—C171.392 (3)C25—H25A0.960
C16—C211.394 (3)C25—H25B0.960
C17—C181.390 (3)C25—H25C0.960
C18—C191.358 (4)
F1···C213.597 (3)C1···H9Bii3.3111
O1···C12.832 (3)C3···H6Aii3.1946
O1···C73.523 (3)C3···H23Cii3.5247
O1···C143.194 (3)C4···H6Aii3.0348
O2···C12.844 (3)C4···H23Cii3.1830
O2···C83.517 (3)C6···H4Aiv3.4001
O2···C143.185 (3)C6···H20xi3.5732
O3···C12.900 (3)C8···H1iv3.5015
C2···C52.919 (3)C8···H18v3.4780
C2···C82.759 (3)C9···H1iv3.3551
C2···C153.009 (3)C11···H23Avi3.4709
C2···C233.367 (3)C11···H23Cvi3.5698
C3···C62.918 (4)C11···H24Axii3.3105
C3···C143.222 (3)C12···H9Bii3.3236
C3···C233.036 (4)C12···H24Cii3.2611
C4···C72.809 (4)C13···H9Bii3.3720
C7···C132.755 (3)C14···H17ii3.4730
C7···C143.463 (3)C14···H22Biii3.3846
C7···C233.144 (3)C15···H22Cvi3.3203
C8···C112.806 (3)C15···H25Bix3.3106
C8···C143.451 (3)C16···H9Aix3.2382
C8···C253.162 (3)C16···H22Avi3.3468
C9···C122.918 (4)C16···H22Cvi3.0316
C10···C132.941 (3)C16···H25Bix3.2531
C12···C143.142 (3)C17···H9Aix3.0860
C12···C253.099 (3)C17···H21iv3.4376
C13···C153.203 (3)C17···H22Avi3.1996
C13···C253.452 (3)C17···H22Cvi3.5190
C14···C213.009 (3)C17···H24Bix3.3980
C16···C192.761 (3)C17···H25Ai3.2675
C17···C202.771 (4)C17···H25Bi3.5667
C18···C212.754 (4)C17···H14iv3.54 (3)
F1···C4i3.474 (3)C18···H9Aix3.0056
F1···C6i3.512 (3)C18···H21iv3.1224
F1···C7i3.535 (3)C18···H22Avi3.3064
O1···O3ii3.534 (3)C18···H25Ai3.1618
O1···C23ii3.494 (4)C19···H9Aix3.0437
O2···C22iii3.533 (4)C19···H20x3.4586
O3···O1iv3.534 (3)C19···H22Avi3.5298
C4···F1v3.474 (3)C20···H6Bix3.5580
C6···F1v3.512 (3)C20···H9Aix3.1827
C7···F1v3.535 (3)C20···H18ii3.4206
C16···C22vi3.588 (4)C20···H20x3.1976
C22···O2vii3.533 (4)C21···H9Aix3.2544
C22···C16viii3.588 (4)C21···H18ii3.1313
C23···O1iv3.494 (4)C21···H22Avi3.5814
F1···H182.5290C21···H22Cvi3.1694
F1···H202.5297C21···H25Bix3.5623
O1···H12.6521C22···H21vii3.5200
O1···H4A2.8387C22···H14vii3.19 (3)
O1···H4B2.5043C23···H4Biv3.4377
O1···H23B3.4520C23···H11Aviii3.1848
O1···H143.50 (3)C23···H24Aix3.1156
O2···H12.6498C23···H24Bix3.3204
O2···H11A2.8347C24···H11Bxii3.3831
O2···H11B2.4886C24···H23Axi3.2261
O2···H25A3.5198C24···H23Bxi3.4164
O2···H143.02 (3)C24···H24Axii3.3320
O3···H6A2.4523C24···H25Aiv3.3600
O3···H6B2.6557C24···H25Civ3.4827
O3···H9A2.4322C25···H17v3.2327
O3···H9B2.7096C25···H18v3.3155
O3···H153.31 (3)C25···H24Bii3.3827
C1···H152.65 (3)C25···H24Cii3.4616
C2···H4A2.9317H1···O3ii3.5083
C2···H4B3.3091H1···C8ii3.5015
C2···H6A3.1832H1···C9ii3.3551
C2···H6B3.0345H1···H9Bii2.5347
C2···H23B2.8394H1···H22Biii3.3533
C2···H143.27 (3)H1···H15ii3.5543
C2···H152.76 (3)H4A···F1v2.6922
C3···H12.6867H4A···C6ii3.4001
C3···H6B3.3883H4A···H6Aii2.4346
C3···H23A3.3393H4A···H21vii3.4827
C3···H23B2.6914H4A···H22Cii3.5817
C3···H153.59 (3)H4A···H23Cii3.1875
C4···H6A3.3095H4B···O2vii3.0419
C4···H6B2.7999H4B···C23ii3.4377
C4···H22A2.7237H4B···H6Aii3.0997
C4···H22B2.6671H4B···H23Cii2.5189
C4···H22C3.3330H6A···F1xi3.2287
C4···H23A2.6551H6A···O1iv3.0975
C4···H23B2.6606H6A···C3iv3.1946
C4···H23C3.3172H6A···C4iv3.0348
C6···H4A2.7173H6A···H4Aiv2.4346
C6···H4B3.3234H6A···H4Biv3.0997
C6···H22A2.6471H6A···H20xi3.5224
C6···H22B3.3240H6B···F1v2.8599
C6···H22C2.6962H6B···C20xi3.5580
C6···H23A3.3434H6B···H20xi2.8574
C6···H23B2.6773H9A···C16xi3.2382
C6···H23C2.7096H9A···C17xi3.0860
C7···H13.1660H9A···C18xi3.0056
C7···H4A3.1005H9A···C19xi3.0437
C7···H23B2.8257H9A···C20xi3.1827
C7···H23C3.5123H9A···C21xi3.2544
C7···H153.04 (3)H9A···H17xi3.5637
C8···H13.1658H9A···H18v3.3955
C8···H11A3.1173H9A···H18xi3.4535
C8···H25A2.8550H9B···O2iv3.0258
C8···H25B3.5231H9B···C1iv3.3111
C8···H153.40 (3)H9B···C12iv3.3236
C9···H11A2.7191H9B···C13iv3.3720
C9···H11B3.3179H9B···H1iv2.5347
C9···H24A3.3260H9B···H25Aiv3.2878
C9···H24B2.6728H11A···O2iv3.3418
C9···H24C2.6682H11A···C23vi3.1848
C9···H25A2.6849H11A···H22Bvi3.2970
C9···H25B2.6957H11A···H22Cvi3.4992
C9···H25C3.3375H11A···H23Avi2.5987
C11···H9A3.3094H11A···H23Cvi2.9148
C11···H9B2.7892H11A···H24Axii2.9207
C11···H24A2.6947H11B···C24xii3.3831
C11···H24B3.3354H11B···H11Bxiii3.5508
C11···H24C2.6797H11B···H23Avi3.5428
C11···H25A2.6776H11B···H23Cvi3.5355
C11···H25B3.3292H11B···H24Axii2.8542
C11···H25C2.6784H11B···H24Cii3.2402
C12···H12.7208H11B···H24Cxii3.1172
C12···H9B3.3688H17···O1iv2.8952
C12···H25A2.7712H17···C14iv3.4730
C12···H25C3.4135H17···C25i3.2327
C12···H143.31 (3)H17···H9Aix3.5637
C13···H9A3.2125H17···H21iv3.3260
C13···H9B3.0200H17···H22Avi3.5506
C13···H11A2.9274H17···H24Bix3.1705
C13···H11B3.3065H17···H25Ai2.8640
C13···H25A2.9519H17···H25Bi2.8858
C13···H143.02 (3)H17···H25Ci3.4576
C13···H153.15 (3)H17···H14iv3.0895
C14···H212.7346H18···O3i3.4484
C15···H13.2578H18···C8i3.4780
C15···H172.6261H18···C20iv3.4206
C15···H212.6687H18···C21iv3.1313
C15···H23B3.3580H18···C25i3.3155
C16···H183.2625H18···H9Aix3.4535
C16···H203.2668H18···H9Ai3.3955
C16···H142.60 (3)H18···H20iv3.3044
C17···H213.2216H18···H21iv2.7628
C17···H152.60 (3)H18···H25Ai2.6772
C18···H203.2365H18···H25Bi3.1027
C19···H173.2011H20···F1x3.0448
C19···H213.1964H20···O3ix3.5868
C20···H183.2361H20···C6ix3.5732
C21···H173.2251H20···C19x3.4586
C21···H142.67 (3)H20···C20x3.1976
C21···H153.33 (3)H20···H6Aix3.5224
C22···H4A2.6483H20···H6Bix2.8574
C22···H4B2.7210H20···H18ii3.3044
C22···H6A2.7709H20···H20x2.6610
C22···H6B2.5677H21···C17ii3.4376
C22···H23A2.6688H21···C18ii3.1224
C22···H23B3.3055H21···C22iii3.5200
C22···H23C2.6427H21···H4Aiii3.4827
C23···H4A3.3211H21···H17ii3.3260
C23···H4B2.6184H21···H18ii2.7628
C23···H6A2.5950H21···H22Aiii2.7368
C23···H6B3.3338H21···H22Biii3.4731
C23···H22A3.3113H21···H22Cvi3.3746
C23···H22B2.6714H22A···C16viii3.3468
C23···H22C2.6239H22A···C17viii3.1996
C24···H9A2.7833H22A···C18viii3.3064
C24···H9B2.5485H22A···C19viii3.5298
C24···H11A2.6092H22A···C21viii3.5814
C24···H11B2.7298H22A···H17viii3.5506
C24···H25A3.3190H22A···H21vii2.7368
C24···H25B2.6590H22A···H14vii2.9242
C24···H25C2.6697H22B···O2vii2.6029
C25···H9A2.5878H22B···C14vii3.3846
C25···H9B3.3230H22B···H1vii3.3533
C25···H11A3.3249H22B···H11Aviii3.2970
C25···H11B2.6250H22B···H21vii3.4731
C25···H24A2.6618H22B···H14vii2.6050
C25···H24B2.6684H22C···C15viii3.3203
C25···H24C3.3184H22C···C16viii3.0316
H1···H142.3060H22C···C17viii3.5190
H1···H153.5473H22C···C21viii3.1694
H4A···H6B2.6867H22C···H4Aiv3.5817
H4A···H22A2.5078H22C···H11Aviii3.4992
H4A···H22B2.8608H22C···H21viii3.3746
H4A···H22C3.5429H22C···H14viii3.5369
H4A···H23A3.5130H23A···O2vii3.2088
H4A···H23B3.5669H23A···C11viii3.4709
H4B···H22A3.0561H23A···C24ix3.2261
H4B···H22B2.5231H23A···H11Aviii2.5987
H4B···H22C3.5691H23A···H11Bviii3.5428
H4B···H23A2.4253H23A···H24Aix2.4997
H4B···H23B2.8818H23A···H24Bix3.1267
H4B···H23C3.5018H23A···H25Cix3.2102
H6A···H22A3.0515H23B···O1iv3.0772
H6A···H22C2.6270H23B···C24ix3.4164
H6A···H23A3.4987H23B···H24Aix3.0844
H6A···H23B2.7933H23B···H24Bix2.8856
H6A···H23C2.4373H23B···H25Bix3.2722
H6B···H22A2.3597H23B···H25Cix3.4810
H6B···H22B3.4599H23C···O1iv3.0534
H6B···H22C2.8171H23C···C3iv3.5247
H6B···H23B3.5981H23C···C4iv3.1830
H6B···H23C3.5109H23C···C11viii3.5698
H9A···H24B2.6192H23C···H4Aiv3.1875
H9A···H24C3.0991H23C···H4Biv2.5189
H9A···H25A2.7968H23C···H11Aviii2.9148
H9A···H25B2.4202H23C···H11Bviii3.5355
H9A···H25C3.4894H23C···H24Aix3.3030
H9B···H11A2.6795H23C···H24Bix3.4221
H9B···H24A3.4538H24A···C11xii3.3105
H9B···H24B2.7544H24A···C23xi3.1156
H9B···H24C2.3679H24A···C24xii3.3320
H9B···H25B3.4901H24A···H11Axii2.9207
H11A···H24A2.8602H24A···H11Bxii2.8542
H11A···H24B3.4971H24A···H23Axi2.4997
H11A···H24C2.4211H24A···H23Bxi3.0844
H11A···H25A3.5841H24A···H23Cxi3.3030
H11A···H25C3.5165H24A···H24Axii2.8015
H11B···H24A2.5642H24A···H24Cxii3.0825
H11B···H24B3.5944H24B···C17xi3.3980
H11B···H24C3.0192H24B···C23xi3.3204
H11B···H25A2.8774H24B···C25iv3.3827
H11B···H25B3.5111H24B···H17xi3.1705
H11B···H25C2.4423H24B···H23Axi3.1267
H17···H182.3213H24B···H23Bxi2.8856
H17···H152.3945H24B···H23Cxi3.4221
H20···H212.3081H24B···H25Aiv2.8715
H21···H142.1556H24B···H25Civ3.0227
H21···H153.5935H24C···O2iv2.8628
H22A···H23A3.5554H24C···C12iv3.2611
H22A···H23C3.5135H24C···C25iv3.4616
H22B···H23A2.5079H24C···H11Biv3.2402
H22B···H23B3.5474H24C···H11Bxii3.1172
H22B···H23C2.9393H24C···H24Axii3.0825
H22C···H23A2.9083H24C···H25Aiv2.9694
H22C···H23B3.4988H24C···H25Civ3.1036
H22C···H23C2.4290H25A···C17v3.2675
H23B···H152.7912H25A···C18v3.1618
H24A···H25A3.5416H25A···C24ii3.3600
H24A···H25B2.9248H25A···H9Bii3.2878
H24A···H25C2.4867H25A···H17v2.8640
H24B···H25A3.5415H25A···H18v2.6772
H24B···H25B2.4823H25A···H24Bii2.8715
H24B···H25C2.9505H25A···H24Cii2.9694
H24C···H25B3.5378H25B···O1xi3.5309
H24C···H25C3.5428H25B···C15xi3.3106
H14···H152.71 (4)H25B···C16xi3.2531
F1···H4Ai2.6922H25B···C17v3.5667
F1···H6Aix3.2287H25B···C21xi3.5623
F1···H6Bi2.8599H25B···H17v2.8858
F1···H20x3.0448H25B···H18v3.1027
O1···H6Aii3.0975H25B···H23Bxi3.2722
O1···H17ii2.8952H25C···O1xi3.5911
O1···H23Bii3.0772H25C···C24ii3.4827
O1···H23Cii3.0534H25C···H17v3.4576
O1···H25Bix3.5309H25C···H23Axi3.2102
O1···H25Cix3.5911H25C···H23Bxi3.4810
O1···H15ii2.74 (3)H25C···H24Bii3.0227
O2···H4Biii3.0419H25C···H24Cii3.1036
O2···H9Bii3.0258H14···C17ii3.54 (3)
O2···H11Aii3.3418H14···C22iii3.19 (3)
O2···H22Biii2.6029H14···H17ii3.0895
O2···H23Aiii3.2088H14···H22Aiii2.9242
O2···H24Cii2.8628H14···H22Biii2.6050
O3···H1iv3.5083H14···H22Cvi3.5369
O3···H18v3.4484H15···O1iv2.74 (3)
O3···H20xi3.5868H15···H1iv3.5543
C7—O3—C8117.86 (16)C5—C4—H4A108.816
C2—C1—C13109.06 (17)C5—C4—H4B108.809
C2—C1—C14112.04 (15)H4A—C4—H4B107.675
C13—C1—C14110.00 (17)C5—C6—H6A108.873
C1—C2—C3118.84 (18)C5—C6—H6B108.870
C1—C2—C7122.35 (18)C7—C6—H6A108.879
C3—C2—C7118.81 (18)C7—C6—H6B108.878
O1—C3—C2121.1 (2)H6A—C6—H6B107.714
O1—C3—C4121.5 (3)C8—C9—H9A108.964
C2—C3—C4117.4 (2)C8—C9—H9B108.967
C3—C4—C5113.74 (19)C10—C9—H9A108.960
C4—C5—C6108.50 (17)C10—C9—H9B108.949
C4—C5—C22111.7 (2)H9A—C9—H9B107.764
C4—C5—C23108.13 (18)C10—C11—H11A108.599
C6—C5—C22110.10 (19)C10—C11—H11B108.596
C6—C5—C23109.69 (17)C12—C11—H11A108.585
C22—C5—C23108.70 (18)C12—C11—H11B108.593
C5—C6—C7113.47 (18)H11A—C11—H11B107.567
O3—C7—C2122.94 (18)C1—C14—H14119.2 (16)
O3—C7—C6110.85 (17)C15—C14—H14115.5 (16)
C2—C7—C6126.20 (19)C14—C15—H15117.5 (14)
O3—C8—C9110.75 (17)C16—C15—H15115.4 (14)
O3—C8—C13122.79 (18)C16—C17—H17119.438
C9—C8—C13126.46 (18)C18—C17—H17119.442
C8—C9—C10113.10 (19)C17—C18—H18120.662
C9—C10—C11108.21 (16)C19—C18—H18120.663
C9—C10—C24109.18 (19)C19—C20—H20121.137
C9—C10—C25110.37 (17)C21—C20—H20121.142
C11—C10—C24110.12 (18)C16—C21—H21118.893
C11—C10—C25109.78 (19)C20—C21—H21118.900
C24—C10—C25109.18 (17)C5—C22—H22A109.474
C10—C11—C12114.68 (17)C5—C22—H22B109.466
O2—C12—C11121.55 (19)C5—C22—H22C109.466
O2—C12—C13120.7 (2)H22A—C22—H22B109.474
C11—C12—C13117.8 (2)H22A—C22—H22C109.478
C1—C13—C8122.58 (18)H22B—C22—H22C109.470
C1—C13—C12119.06 (18)C5—C23—H23A109.470
C8—C13—C12118.28 (19)C5—C23—H23B109.469
C1—C14—C15125.1 (2)C5—C23—H23C109.469
C14—C15—C16126.9 (2)H23A—C23—H23B109.474
C15—C16—C17120.00 (19)H23A—C23—H23C109.481
C15—C16—C21122.54 (19)H23B—C23—H23C109.464
C17—C16—C21117.45 (18)C10—C24—H24A109.469
C16—C17—C18121.1 (2)C10—C24—H24B109.475
C17—C18—C19118.7 (3)C10—C24—H24C109.473
F1—C19—C18119.2 (3)H24A—C24—H24B109.474
F1—C19—C20117.9 (3)H24A—C24—H24C109.474
C18—C19—C20122.8 (3)H24B—C24—H24C109.463
C19—C20—C21117.7 (3)C10—C25—H25A109.471
C16—C21—C20122.2 (2)C10—C25—H25B109.473
C2—C1—H1108.563C10—C25—H25C109.459
C13—C1—H1108.543H25A—C25—H25B109.473
C14—C1—H1108.553H25A—C25—H25C109.466
C3—C4—H4A108.819H25B—C25—H25C109.484
C3—C4—H4B108.810
C7—O3—C8—C9172.44 (13)O3—C8—C9—C10159.36 (13)
C7—O3—C8—C137.8 (3)O3—C8—C13—C14.2 (3)
C8—O3—C7—C27.0 (3)O3—C8—C13—C12179.08 (14)
C8—O3—C7—C6172.08 (13)C9—C8—C13—C1175.50 (15)
C2—C1—C13—C815.0 (3)C9—C8—C13—C121.2 (3)
C2—C1—C13—C12168.36 (14)C13—C8—C9—C1020.9 (3)
C13—C1—C2—C3164.10 (14)C8—C9—C10—C1144.1 (2)
C13—C1—C2—C715.7 (3)C8—C9—C10—C24163.94 (14)
C2—C1—C14—C1544.9 (3)C8—C9—C10—C2576.05 (19)
C14—C1—C2—C373.9 (2)C9—C10—C11—C1252.5 (3)
C14—C1—C2—C7106.30 (19)C24—C10—C11—C12171.74 (16)
C13—C1—C14—C1576.6 (3)C25—C10—C11—C1268.0 (2)
C14—C1—C13—C8108.27 (19)C10—C11—C12—O2145.70 (18)
C14—C1—C13—C1268.4 (2)C10—C11—C12—C1335.6 (3)
C1—C2—C3—O12.8 (3)O2—C12—C13—C110.2 (3)
C1—C2—C3—C4174.82 (14)O2—C12—C13—C8172.99 (17)
C1—C2—C7—O35.9 (3)C11—C12—C13—C1168.47 (15)
C1—C2—C7—C6175.25 (14)C11—C12—C13—C88.3 (3)
C3—C2—C7—O3173.98 (15)C1—C14—C15—C16175.85 (18)
C3—C2—C7—C64.9 (3)C14—C15—C16—C17173.4 (2)
C7—C2—C3—O1177.32 (16)C14—C15—C16—C215.1 (4)
C7—C2—C3—C45.0 (3)C15—C16—C17—C18177.44 (18)
O1—C3—C4—C5146.87 (19)C15—C16—C21—C20177.67 (18)
C2—C3—C4—C535.5 (3)C17—C16—C21—C200.9 (3)
C3—C4—C5—C653.4 (2)C21—C16—C17—C181.1 (3)
C3—C4—C5—C22174.90 (15)C16—C17—C18—C190.5 (4)
C3—C4—C5—C2365.5 (2)C17—C18—C19—F1179.2 (2)
C4—C5—C6—C743.3 (2)C17—C18—C19—C200.4 (4)
C22—C5—C6—C7165.83 (17)F1—C19—C20—C21178.92 (19)
C23—C5—C6—C774.6 (2)C18—C19—C20—C210.7 (4)
C5—C6—C7—O3165.12 (14)C19—C20—C21—C160.0 (4)
C5—C6—C7—C215.9 (3)
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x1, y, z; (iii) x+1, y+1/2, z+1/2; (iv) x+1, y, z; (v) x1, y+1/2, z1/2; (vi) x+2, y+1/2, z+1/2; (vii) x+1, y1/2, z+1/2; (viii) x+2, y1/2, z+1/2; (ix) x, y+1/2, z+1/2; (x) x+2, y+1, z+1; (xi) x, y+1/2, z1/2; (xii) x+2, y+1, z; (xiii) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22B···O2vii0.962.603.533 (4)163
Symmetry code: (vii) x+1, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22B···O2i0.9602.60293.533 (4)163.0
Symmetry code: (i) x+1, y1/2, z+1/2.
Acknowledgements top

Financial support from the Korea Institute of Science and Technology (KIST) is gratefully acknowledged.

references
References top

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.

Cha, J. H., Min, S.-J., Cho, Y. S., Lee, J. K. & Park, J. (2013). Acta Cryst. E69, o397.

Cha, J. H., Pae, A. N., Lee, J. K. & Cho, Y. S. (2012). Acta Cryst. E68, o454.

Lee, J. K., Min, S.-J., Cho, Y. S., Lee, K. S. & Cha, J. H. (2012). Acta Cryst. E68, o1947.

Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.

Rigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.

Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.