organic compounds
9-(2,4-Difluorophenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione
aDepartment of Physics, Seethalakshmi Ramaswami College (Autonomous), Tiruchirappalli 620 002, India, bDepartment of Physics, K. Ramakrishnan College of Engineering, Samayapuram, Tiruchirappalli 621 112, India, cDepartment of Chemistry, Sri Krishna Engineering College, Panapakkam, Thambaram 601 301, India, dDepartment of Chemistry, Chemistry Wing DDE, Annamalai University, Annamalainagar 608 002, India, and eDepartment of Chemistry, S.K.P. Engineering College, Thiruvanamalai 606 611, India
*Correspondence e-mail: raghema2000@yahoo.co.in
In the title compound, C23H24F2O3, the central pyran ring has a flat-boat conformation, whereas the two fused cyclohexenone 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 difluorophenyl ring are almost normal to each other, making a dihedral angle of 87.55 (4)°. In the crystal, molecules are linked by pairs of C—H⋯O hydrogen bonds, forming inversion dimers with an R22(8) ring motif. The F atom at position 2 on the difluorophenyl ring is disordered over the 2- and 6-positions, and has a refined occupancy ratio of 0.932 (3):0.068 (3).
CCDC reference: 985439
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
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Data collection: APEX2 (Bruker, 2004); cell 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).
Supporting information
CCDC reference: 985439
10.1107/S1600536814002761/su2696sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814002761/su2696Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814002761/su2696Isup3.cml
5,5-dimethylcyclohexane-1,3-dione (1.15 g, 16 mmol) was treated with 2,4-difluorobenzaldehyde (0.6 g, 8 mmol) in ethanol (10 ml). The reaction mixture was heated for 5 min. After cooling to room temperature, a solid started to separate out. This solid was filtered, dried and then recrystallized from ethanol to yield colourless block-like crystals of the title compound [Yield 0.95 g; 80%].
Atom F1 on the difluorophenyl ring is slightly disordered, being attached to atoms C23 and C19 with a refined occupancy ratio of 0.932 (3):0.068 (3), for atoms F1:F1' and H19:H23. The H atoms were included in calculated positions and treated as riding atoms: C-H = 0.93, 0.98, 0.97 and 0.96 Å for CH(aromatic), CH, CH2 and CH3 H atoms, respectively, with Uiso(H) = 1.5Ueq(C-methyl) and = 1.2Ueq(C) for other H atoms.
Data collection: APEX2 (Bruker, 2004); cell
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).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 |
C23H24F2O3 | γ = 63.406 (2)° |
Mr = 386.42 | V = 996.03 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.6810 (4) Å | Mo Kα radiation |
b = 10.4290 (4) Å | µ = 0.10 mm−1 |
c = 11.8840 (5) Å | T = 293 K |
α = 69.288 (2)° | 0.30 × 0.20 × 0.20 mm |
β = 74.895 (2)° |
Bruker Kappa APEXII CCD diffractometer | 6738 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 4248 reflections with I > 2σ(I) |
Tmin = 0.972, Tmax = 0.981 | Rint = 0.026 |
23107 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.24 e Å−3 |
6738 reflections | Δρmin = −0.18 e Å−3 |
267 parameters |
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 |
Symmetry code: (i) −x+2, −y, −z+1. |
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) −x+2, −y, −z+1. |
Acknowledgements
SR thanks the University Grants Commission for financial support of this work (grant MRP– 4335/12). The authors are thankful to the SAIF, IIT Madras, for the data collection.
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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.
Xanthene is the parent compound of a number of naturally occurring substances and some synthetic dyes. Xanthene derivatives are used as dyes (Hilderbrand & Weissleder, 2007) and are used in medicine as they possess biological properties like antibacterial, antiviral and anti-inflammatory activities (Jonathan et al., 1988). Ehretianone, a quinonoid xanthene was reported to possess anti-snake venom activity (Selvanayagam et al., 1996; Lambert et al., 1997; Poupelin et al., 1978; Hideo, 1981). In view of the importance of the Xanthene derivatives we have synthesized the title compound and report herein on its crystal structure.
In the title molecule, Fig. 1, the pyran ring (O2/C5-C8/C13) has a flat boat conformation [Q = 0.1721 (13) Å, θ = 75.4 (4)° and φ = 186.9 (5)°] with a deviation for atoms O2 [0.1999 (12) Å] and C7 [0.0898 (9) Å] from the mean plane of the other four atoms. The two fused cyclohexenone rings adopt envelope conformations with puckering parameter (Cremer & Pople, 1975) Q = 0.4417 (15) Å, θ = 55.22 (19)° and φ = 116.4 (2)° for ring (C1-C6) and Q = 0.4715 (16) Å, θ = 59.08 (19)° and φ = 179.5 (2)° for ring (C8-C13). Atoms C3 and C11 are the flap atoms being situated out of the mean plane of the respective ring by 0.3118 (9) and 0.3324 (10) Å. The dihedral angle between the mean plane of the central pyran ring (O2/C5-C8/C13) and the difluorophenyl ring (C18-C23) is 87.55 (4)°.
In the crystal, molecules are linked by a pair of C-H···O hydrogen bonds (Fig. 2 and Table 1) forming inversion dimers with an R22(8) ring motif (Bernstein et al., 1995).