9-(2,4-Di-fluoro-phen-yl)-3,3,6,6-tetra-methyl-3,4,5,6,7,9-hexa-hydro-2H-xanthene-1,8-dione.

In the title compound, C23H24F2O3, the central pyran ring has a flat-boat conformation, whereas the two fused cyclo-hexenone rings adopt envelope conformations, with the C atom bearing the dimethyl substituent being the flap atom in each case. The pyran ring mean plane and the di-fluoro-phenyl ring are almost normal to each other, making a dihedral angle of 87.55 (4)°. In the crystal, mol-ecules are linked by pairs of C-H⋯O hydrogen bonds, forming inversion dimers with an R 2 (2)(8) ring motif. The F atom at position 2 on the di-fluoro-phenyl ring is disordered over the 2- and 6-positions, and has a refined occupancy ratio of 0.932 (3):0.068 (3).

Related literature

For the synthesis of xanthenes, see: Vanag & Stankevich (1960 ▶); Hilderbrand & Weissleder (2007 ▶). For their pharmaceutical properties, see: Jonathan et al. (1988 ▶); Lambert et al. (1997 ▶); Poupelin et al. (1978 ▶); Hideo (1981 ▶); Selvanayagam et al. (1996 ▶). For related structures, see: Sughanya & Sureshbabu (2012 ▶); Sureshbabu & Sughanya (2013 ▶). For ring conformation analysis, see: Cremer & Pople (1975 ▶). For hydrogen-bonding graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C23H24F2O3

M = 386.42

Triclinic,

a = 9.6810 (4) Å

b = 10.4290 (4) Å

c = 11.8840 (5) Å

α = 69.288 (2)°

β = 74.895 (2)°

γ = 63.406 (2)°

V = 996.03 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.972, T max = 0.981

23107 measured reflections

6738 independent reflections

4248 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.147

S = 1.03

6738 reflections

267 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814002761/su2696sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002761/su2696Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814002761/su2696Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C23H24F2O3	Z = 2
Mr = 386.42	F(000) = 408
Triclinic, P1	Dx = 1.288 Mg m−3
a = 9.6810 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.4290 (4) Å	Cell parameters from 8029 reflections
c = 11.8840 (5) Å	θ = 2.8–30.5°
α = 69.288 (2)°	µ = 0.10 mm−1
β = 74.895 (2)°	T = 293 K
γ = 63.406 (2)°	Block, colourless
V = 996.03 (7) Å3	0.30 × 0.20 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	6738 independent reflections
Radiation source: fine-focus sealed tube	4248 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω and φ scan	θmax = 31.9°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→14
Tmin = 0.972, Tmax = 0.981	k = −10→15
23107 measured reflections	l = −17→17

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H-atom parameters constrained
wR(F2) = 0.147	w = 1/[σ2(Fo2) + (0.0674P)2 + 0.1104P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
6738 reflections	Δρmax = 0.24 e Å−3
267 parameters	Δρmin = −0.18 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq	Occ. (<1)
F1	0.58177 (9)	0.33825 (10)	0.21213 (9)	0.0634 (3)	0.932 (3)
F1'	1.0560 (15)	0.0461 (17)	0.3554 (14)	0.078 (5)	0.068 (3)
F2	0.72300 (13)	0.44738 (12)	0.50286 (9)	0.0828 (3)
O1	0.84119 (12)	−0.15460 (12)	0.39286 (9)	0.0627 (3)
O2	0.65242 (9)	0.17594 (9)	0.02533 (7)	0.0434 (2)
O3	1.11867 (11)	0.17515 (13)	0.07618 (10)	0.0686 (3)
C1	0.74840 (14)	−0.10446 (13)	0.32037 (11)	0.0420 (3)
C2	0.63396 (15)	−0.17246 (15)	0.33580 (11)	0.0473 (3)
H2A	0.6041	−0.2087	0.4218	0.057*
H2B	0.6856	−0.2578	0.3029	0.057*
C3	0.48605 (14)	−0.06656 (14)	0.27502 (11)	0.0435 (3)
C4	0.53389 (14)	0.00773 (14)	0.14367 (11)	0.0430 (3)
H4A	0.5750	−0.0643	0.0971	0.052*
H4B	0.4424	0.0891	0.1094	0.052*
C5	0.65262 (13)	0.06655 (12)	0.13208 (10)	0.0373 (2)
C6	0.75128 (12)	0.01894 (12)	0.21271 (10)	0.0371 (2)
C7	0.86725 (12)	0.08662 (13)	0.19491 (10)	0.0381 (2)
H7	0.9692	0.0051	0.2097	0.046*
C8	0.87933 (12)	0.17859 (13)	0.06498 (10)	0.0380 (2)
C9	1.01106 (13)	0.22456 (14)	0.01719 (12)	0.0465 (3)
C10	1.01073 (15)	0.32985 (16)	−0.10760 (13)	0.0549 (3)
H10A	1.0736	0.2719	−0.1646	0.066*
H10B	1.0605	0.3935	−0.1099	0.066*
C11	0.85044 (15)	0.42923 (14)	−0.15076 (12)	0.0476 (3)
C12	0.76661 (16)	0.32723 (14)	−0.13191 (11)	0.0467 (3)
H12A	0.6587	0.3880	−0.1454	0.056*
H12B	0.8143	0.2703	−0.1911	0.056*
C13	0.77272 (13)	0.22295 (13)	−0.00826 (10)	0.0386 (2)
C14	0.38365 (17)	0.05031 (19)	0.34291 (15)	0.0644 (4)
H14A	0.4406	0.1052	0.3437	0.097*
H14B	0.3532	0.0020	0.4246	0.097*
H14C	0.2925	0.1174	0.3032	0.097*
C15	0.39565 (18)	−0.15434 (18)	0.27371 (14)	0.0616 (4)
H15A	0.3623	−0.1999	0.3555	0.092*
H15B	0.4616	−0.2302	0.2333	0.092*
H15C	0.3064	−0.0880	0.2316	0.092*
C16	0.75801 (18)	0.54296 (16)	−0.07819 (15)	0.0622 (4)
H16A	0.6554	0.6002	−0.1024	0.093*
H16B	0.8098	0.6083	−0.0931	0.093*
H16C	0.7506	0.4920	0.0066	0.093*
C17	0.8681 (2)	0.51037 (19)	−0.28546 (14)	0.0716 (4)
H17A	0.7671	0.5682	−0.3125	0.107*
H17B	0.9287	0.4387	−0.3308	0.107*
H17C	0.9196	0.5752	−0.2976	0.107*
C18	0.82627 (12)	0.18056 (13)	0.28097 (10)	0.0375 (2)
C19	0.92946 (14)	0.15185 (14)	0.35771 (11)	0.0431 (3)
H19	1.0239	0.0699	0.3589	0.052*	0.932 (3)
C20	0.89720 (16)	0.24020 (16)	0.43221 (12)	0.0514 (3)
H20	0.9683	0.2190	0.4825	0.062*
C21	0.75792 (18)	0.35938 (16)	0.42986 (12)	0.0528 (3)
C22	0.64974 (16)	0.39404 (15)	0.35770 (13)	0.0540 (3)
H22	0.5549	0.4753	0.3580	0.065*
C23	0.68774 (14)	0.30316 (14)	0.28486 (11)	0.0454 (3)
H23	0.6157	0.3255	0.2350	0.054*	0.068 (3)

	U11	U22	U33	U12	U13	U23
F1	0.0438 (5)	0.0656 (6)	0.0797 (7)	0.0015 (4)	−0.0322 (4)	−0.0315 (5)
F1'	0.058 (8)	0.079 (10)	0.093 (11)	−0.011 (7)	−0.035 (7)	−0.023 (8)
F2	0.1159 (8)	0.0833 (7)	0.0739 (6)	−0.0448 (6)	−0.0094 (6)	−0.0435 (5)
O1	0.0698 (6)	0.0637 (6)	0.0568 (6)	−0.0285 (5)	−0.0337 (5)	0.0026 (5)
O2	0.0467 (4)	0.0482 (5)	0.0423 (4)	−0.0277 (4)	−0.0157 (4)	−0.0010 (4)
O3	0.0419 (5)	0.0823 (7)	0.0837 (7)	−0.0312 (5)	−0.0171 (5)	−0.0095 (6)
C1	0.0434 (6)	0.0413 (6)	0.0406 (6)	−0.0136 (5)	−0.0113 (5)	−0.0101 (5)
C2	0.0513 (7)	0.0478 (7)	0.0417 (6)	−0.0244 (6)	−0.0080 (5)	−0.0031 (5)
C3	0.0430 (6)	0.0481 (7)	0.0434 (6)	−0.0237 (5)	−0.0058 (5)	−0.0090 (5)
C4	0.0473 (6)	0.0493 (7)	0.0423 (6)	−0.0274 (5)	−0.0126 (5)	−0.0076 (5)
C5	0.0407 (6)	0.0386 (6)	0.0369 (6)	−0.0189 (5)	−0.0086 (4)	−0.0081 (5)
C6	0.0359 (5)	0.0389 (6)	0.0401 (6)	−0.0151 (5)	−0.0085 (4)	−0.0116 (5)
C7	0.0308 (5)	0.0386 (6)	0.0460 (6)	−0.0105 (4)	−0.0119 (4)	−0.0121 (5)
C8	0.0329 (5)	0.0390 (6)	0.0450 (6)	−0.0139 (4)	−0.0050 (4)	−0.0149 (5)
C9	0.0343 (5)	0.0485 (7)	0.0593 (8)	−0.0164 (5)	−0.0029 (5)	−0.0197 (6)
C10	0.0447 (7)	0.0595 (8)	0.0625 (8)	−0.0281 (6)	0.0038 (6)	−0.0163 (7)
C11	0.0523 (7)	0.0446 (7)	0.0515 (7)	−0.0272 (6)	−0.0044 (6)	−0.0101 (6)
C12	0.0575 (7)	0.0482 (7)	0.0432 (7)	−0.0290 (6)	−0.0103 (5)	−0.0086 (5)
C13	0.0394 (6)	0.0396 (6)	0.0425 (6)	−0.0192 (5)	−0.0056 (5)	−0.0124 (5)
C14	0.0524 (8)	0.0734 (10)	0.0679 (9)	−0.0223 (7)	0.0030 (7)	−0.0303 (8)
C15	0.0641 (9)	0.0684 (9)	0.0636 (9)	−0.0449 (8)	−0.0104 (7)	−0.0041 (7)
C16	0.0664 (9)	0.0459 (7)	0.0798 (10)	−0.0208 (7)	−0.0154 (8)	−0.0208 (7)
C17	0.0896 (12)	0.0714 (10)	0.0602 (9)	−0.0517 (10)	−0.0078 (8)	0.0005 (8)
C18	0.0352 (5)	0.0392 (6)	0.0417 (6)	−0.0159 (5)	−0.0115 (4)	−0.0085 (5)
C19	0.0396 (6)	0.0474 (7)	0.0462 (6)	−0.0201 (5)	−0.0148 (5)	−0.0065 (5)
C20	0.0622 (8)	0.0639 (8)	0.0438 (7)	−0.0379 (7)	−0.0165 (6)	−0.0080 (6)
C21	0.0731 (9)	0.0549 (8)	0.0443 (7)	−0.0352 (7)	−0.0045 (6)	−0.0180 (6)
C22	0.0556 (8)	0.0455 (7)	0.0578 (8)	−0.0127 (6)	−0.0085 (6)	−0.0191 (6)
C23	0.0411 (6)	0.0476 (7)	0.0489 (7)	−0.0130 (5)	−0.0157 (5)	−0.0136 (5)

F1—C23	1.3549 (13)	C11—C16	1.5239 (19)
F1'—C19	1.230 (14)	C11—C17	1.5287 (19)
F2—C21	1.3571 (15)	C11—C12	1.5330 (16)
O1—C1	1.2193 (14)	C12—C13	1.4843 (17)
O2—C5	1.3735 (13)	C12—H12A	0.9700
O2—C13	1.3736 (13)	C12—H12B	0.9700
O3—C9	1.2193 (15)	C14—H14A	0.9600
C1—C6	1.4638 (16)	C14—H14B	0.9600
C1—C2	1.5065 (17)	C14—H14C	0.9600
C2—C3	1.5332 (17)	C15—H15A	0.9600
C2—H2A	0.9700	C15—H15B	0.9600
C2—H2B	0.9700	C15—H15C	0.9600
C3—C14	1.522 (2)	C16—H16A	0.9600
C3—C15	1.5292 (17)	C16—H16B	0.9600
C3—C4	1.5299 (17)	C16—H16C	0.9600
C4—C5	1.4851 (15)	C17—H17A	0.9600
C4—H4A	0.9700	C17—H17B	0.9600
C4—H4B	0.9700	C17—H17C	0.9600
C5—C6	1.3389 (14)	C18—C23	1.3819 (17)
C6—C7	1.5112 (14)	C18—C19	1.3904 (14)
C7—C8	1.5089 (16)	C19—C20	1.3804 (18)
C7—C18	1.5207 (16)	C19—H19	0.9300
C7—H7	0.9800	C20—C21	1.363 (2)
C8—C13	1.3388 (15)	C20—H20	0.9300
C8—C9	1.4684 (15)	C21—C22	1.3685 (19)
C9—C10	1.5009 (19)	C22—C23	1.3730 (18)
C10—C11	1.5310 (19)	C22—H22	0.9300
C10—H10A	0.9700	C23—H23	0.9300
C10—H10B	0.9700
C5—O2—C13	118.21 (8)	C11—C12—H12A	109.2
O1—C1—C6	120.42 (11)	C13—C12—H12B	109.2
O1—C1—C2	121.07 (11)	C11—C12—H12B	109.2
C6—C1—C2	118.44 (9)	H12A—C12—H12B	107.9
C1—C2—C3	114.85 (10)	C8—C13—O2	122.43 (10)
C1—C2—H2A	108.6	C8—C13—C12	125.78 (10)
C3—C2—H2A	108.6	O2—C13—C12	111.79 (9)
C1—C2—H2B	108.6	C3—C14—H14A	109.5
C3—C2—H2B	108.6	C3—C14—H14B	109.5
H2A—C2—H2B	107.5	H14A—C14—H14B	109.5
C14—C3—C15	109.58 (11)	C3—C14—H14C	109.5
C14—C3—C4	110.53 (11)	H14A—C14—H14C	109.5
C15—C3—C4	108.14 (10)	H14B—C14—H14C	109.5
C14—C3—C2	110.07 (11)	C3—C15—H15A	109.5
C15—C3—C2	110.10 (11)	C3—C15—H15B	109.5
C4—C3—C2	108.39 (10)	H15A—C15—H15B	109.5
C5—C4—C3	113.01 (9)	C3—C15—H15C	109.5
C5—C4—H4A	109.0	H15A—C15—H15C	109.5
C3—C4—H4A	109.0	H15B—C15—H15C	109.5
C5—C4—H4B	109.0	C11—C16—H16A	109.5
C3—C4—H4B	109.0	C11—C16—H16B	109.5
H4A—C4—H4B	107.8	H16A—C16—H16B	109.5
C6—C5—O2	123.04 (9)	C11—C16—H16C	109.5
C6—C5—C4	125.44 (10)	H16A—C16—H16C	109.5
O2—C5—C4	111.51 (9)	H16B—C16—H16C	109.5
C5—C6—C1	118.82 (10)	C11—C17—H17A	109.5
C5—C6—C7	122.11 (10)	C11—C17—H17B	109.5
C1—C6—C7	119.06 (9)	H17A—C17—H17B	109.5
C8—C7—C6	108.90 (9)	C11—C17—H17C	109.5
C8—C7—C18	110.47 (9)	H17A—C17—H17C	109.5
C6—C7—C18	113.06 (9)	H17B—C17—H17C	109.5
C8—C7—H7	108.1	C23—C18—C19	115.53 (11)
C6—C7—H7	108.1	C23—C18—C7	122.63 (9)
C18—C7—H7	108.1	C19—C18—C7	121.79 (10)
C13—C8—C9	118.38 (11)	F1'—C19—C20	119.4 (6)
C13—C8—C7	122.62 (10)	F1'—C19—C18	118.0 (7)
C9—C8—C7	118.98 (10)	C20—C19—C18	122.57 (12)
O3—C9—C8	120.69 (12)	C20—C19—H19	118.7
O3—C9—C10	121.52 (11)	C18—C19—H19	118.7
C8—C9—C10	117.76 (10)	C21—C20—C19	117.98 (11)
C9—C10—C11	115.71 (10)	C21—C20—H20	121.0
C9—C10—H10A	108.4	C19—C20—H20	121.0
C11—C10—H10A	108.4	F2—C21—C20	119.12 (12)
C9—C10—H10B	108.4	F2—C21—C22	118.00 (13)
C11—C10—H10B	108.4	C20—C21—C22	122.88 (12)
H10A—C10—H10B	107.4	C21—C22—C23	116.87 (12)
C16—C11—C17	109.55 (12)	C21—C22—H22	121.6
C16—C11—C10	110.27 (11)	C23—C22—H22	121.6
C17—C11—C10	110.20 (12)	F1—C23—C22	117.04 (11)
C16—C11—C12	110.34 (11)	F1—C23—C18	118.79 (11)
C17—C11—C12	109.15 (11)	C22—C23—C18	124.17 (11)
C10—C11—C12	107.29 (10)	C22—C23—H23	117.9
C13—C12—C11	112.16 (10)	C18—C23—H23	117.9
C13—C12—H12A	109.2
O1—C1—C2—C3	155.46 (12)	C9—C10—C11—C16	68.74 (15)
C6—C1—C2—C3	−27.60 (16)	C9—C10—C11—C17	−170.19 (12)
C1—C2—C3—C14	−70.82 (14)	C9—C10—C11—C12	−51.47 (15)
C1—C2—C3—C15	168.27 (11)	C16—C11—C12—C13	−70.88 (14)
C1—C2—C3—C4	50.17 (14)	C17—C11—C12—C13	168.68 (12)
C14—C3—C4—C5	73.46 (13)	C10—C11—C12—C13	49.28 (14)
C15—C3—C4—C5	−166.59 (11)	C9—C8—C13—O2	174.81 (10)
C2—C3—C4—C5	−47.24 (14)	C7—C8—C13—O2	−6.63 (17)
C13—O2—C5—C6	9.76 (16)	C9—C8—C13—C12	−5.94 (18)
C13—O2—C5—C4	−168.91 (10)	C7—C8—C13—C12	172.62 (11)
C3—C4—C5—C6	23.38 (17)	C5—O2—C13—C8	−7.66 (16)
C3—C4—C5—O2	−157.99 (10)	C5—O2—C13—C12	173.00 (10)
O2—C5—C6—C1	−176.36 (10)	C11—C12—C13—C8	−23.44 (18)
C4—C5—C6—C1	2.12 (18)	C11—C12—C13—O2	155.88 (10)
O2—C5—C6—C7	2.50 (18)	C8—C7—C18—C23	63.24 (14)
C4—C5—C6—C7	−179.02 (11)	C6—C7—C18—C23	−59.07 (15)
O1—C1—C6—C5	176.86 (12)	C8—C7—C18—C19	−114.03 (11)
C2—C1—C6—C5	−0.10 (17)	C6—C7—C18—C19	123.66 (11)
O1—C1—C6—C7	−2.04 (17)	C23—C18—C19—F1'	−178.2 (9)
C2—C1—C6—C7	−179.00 (10)	C7—C18—C19—F1'	−0.8 (9)
C5—C6—C7—C8	−14.60 (15)	C23—C18—C19—C20	−0.60 (18)
C1—C6—C7—C8	164.25 (10)	C7—C18—C19—C20	176.85 (11)
C5—C6—C7—C18	108.58 (12)	F1'—C19—C20—C21	177.9 (9)
C1—C6—C7—C18	−72.56 (13)	C18—C19—C20—C21	0.34 (19)
C6—C7—C8—C13	16.67 (15)	C19—C20—C21—F2	179.57 (11)
C18—C7—C8—C13	−108.05 (12)	C19—C20—C21—C22	0.3 (2)
C6—C7—C8—C9	−164.77 (10)	F2—C21—C22—C23	−179.89 (12)
C18—C7—C8—C9	70.50 (12)	C20—C21—C22—C23	−0.6 (2)
C13—C8—C9—O3	−172.78 (12)	C21—C22—C23—F1	−179.17 (12)
C7—C8—C9—O3	8.60 (18)	C21—C22—C23—C18	0.3 (2)
C13—C8—C9—C10	5.27 (17)	C19—C18—C23—F1	179.75 (11)
C7—C8—C9—C10	−173.35 (11)	C7—C18—C23—F1	2.32 (18)
O3—C9—C10—C11	−156.79 (13)	C19—C18—C23—C22	0.26 (19)
C8—C9—C10—C11	25.18 (17)	C7—C18—C23—C22	−177.17 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O1i	0.93	2.38	3.3075 (15)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O1i	0.93	2.38	3.3075 (15)	177

Symmetry code: (i) .