Literature DB >> 21202073

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

Mustafa Odabaşoğlu, Muharrem Kaya, Yılmaz Yıldırır, Orhan Büyükgüngör.   

Abstract

In the mol-ecule of the title compound, C(24)H(28)O(4), the three six-membered rings of the xanthene system are not planar, having envelope, boat and envelope conformations. In the crystal structure, C-H⋯O hydrogen bonds link the mol-ecules, generating centrosymmetric R(2) (2)(12), R(4) (4)(28) and R(2) (2)(16) ring motifs and forming a three-dimensional network.

Entities:  

Year:  2008        PMID： 21202073      PMCID： PMC2960936          DOI： 10.1107/S160053680800603X

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For general background, see: Menchen et al. (2003 ▶); Banerjee & Mukherjee (1981 ▶); Nogradi (2003 ▶); Kamel & Shoeb (1964 ▶); Hideo (1981 ▶); Poupelin et al. (1978 ▶); Lambert et al. (1997 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For ring motif details, see: Bernstein et al. (1995 ▶); Etter (1990 ▶). For related literature, see: Horning & Horning (1946 ▶).

Experimental

Crystal data

C24H28O4 M = 380.46 Triclinic, a = 9.346 (5) Å b = 10.314 (5) Å c = 11.733 (5) Å α = 71.089 (5)° β = 84.253 (5)° γ = 73.386 (5)° V = 1025.2 (9) Å3 Z = 2 Mo Kα radiation μ = 0.08 mm−1 T = 296 K 0.66 × 0.54 × 0.41 mm

Data collection

Stoe IPDSII diffractometer Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.947, T max = 0.975 17059 measured reflections 4035 independent reflections 3450 reflections with I > 2σ(I) R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.108 S = 1.04 4035 reflections 253 parameters H-atom parameters constrained Δρmax = 0.16 e Å−3 Δρmin = −0.17 e Å−3 Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680800603X/hk2429sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680800603X/hk2429Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C24H28O4Z = 2
Mr = 380.46F000 = 408
Triclinic, P1Dx = 1.232 Mg m−3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 9.346 (5) ÅCell parameters from 17059 reflections
b = 10.314 (5) Åθ = 1.8–28.0º
c = 11.733 (5) ŵ = 0.08 mm−1
α = 71.089 (5)ºT = 296 K
β = 84.253 (5)ºPrism, colorless
γ = 73.386 (5)º0.66 × 0.54 × 0.41 mm
V = 1025.2 (9) Å3
Stoe IPDSII diffractometer4035 independent reflections
Monochromator: plane graphite3450 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1Rint = 0.033
T = 296 Kθmax = 26.0º
ω–scan rotation methodθmin = 2.2º
Absorption correction: integration(X-RED32; Stoe & Cie, 2002)h = −11→11
Tmin = 0.947, Tmax = 0.975k = −12→12
17059 measured reflectionsl = −14→14
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.109  w = 1/[σ2(Fo2) + (0.0512P)2 + 0.165P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
4035 reflectionsΔρmax = 0.16 e Å−3
253 parametersΔρmin = −0.17 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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 of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/Ueq
O10.32183 (13)0.81707 (14)−0.08171 (10)0.0796 (4)
O20.55478 (9)0.45682 (9)0.26047 (8)0.0459 (2)
O30.03418 (11)0.52647 (13)0.26037 (11)0.0718 (3)
O40.02323 (12)1.09853 (11)0.34873 (10)0.0672 (3)
C10.42493 (13)0.64720 (13)0.09685 (11)0.0431 (3)
C20.43421 (15)0.74638 (14)−0.02413 (12)0.0509 (3)
C30.58637 (16)0.75273 (16)−0.07685 (12)0.0551 (3)
H3A0.57990.8491−0.12850.066*
H3B0.61490.6909−0.12710.066*
C40.70957 (15)0.70997 (14)0.01517 (12)0.0471 (3)
C50.70551 (13)0.56537 (13)0.10549 (12)0.0452 (3)
H5A0.74430.49210.06690.054*
H5B0.76990.54440.17270.054*
C60.55218 (13)0.56175 (12)0.15160 (11)0.0407 (3)
C70.68441 (19)0.82180 (16)0.07936 (15)0.0632 (4)
H7A0.76140.79330.13780.076*
H7B0.58880.83090.11910.076*
H7C0.68720.91160.02150.076*
C80.86223 (17)0.69525 (18)−0.04741 (15)0.0649 (4)
H8A0.87820.6252−0.08820.078*
H8B0.93880.66620.01150.078*
H8C0.86560.7851−0.10480.078*
C90.28957 (13)0.50728 (13)0.25682 (12)0.0436 (3)
C100.15563 (14)0.46043 (16)0.30671 (13)0.0532 (3)
C110.17414 (17)0.32686 (18)0.41176 (15)0.0659 (4)
H11A0.18440.24770.38130.079*
H11B0.08390.33530.46060.079*
C120.30751 (16)0.29219 (16)0.49231 (13)0.0558 (3)
C130.44636 (15)0.29653 (14)0.41151 (13)0.0516 (3)
H13A0.52850.29210.45830.062*
H13B0.47430.21360.38380.062*
C140.42175 (13)0.42701 (13)0.30557 (11)0.0422 (3)
C150.2821 (2)0.4017 (2)0.55902 (16)0.0745 (5)
H15A0.26860.49500.50170.089*
H15B0.36720.38020.60820.089*
H15C0.19460.39880.60910.089*
C160.3294 (2)0.1439 (2)0.58349 (18)0.0846 (6)
H16A0.41540.12200.63170.102*
H16B0.34380.07510.54160.102*
H16C0.24260.14130.63450.102*
C170.27361 (13)0.64451 (13)0.15483 (12)0.0452 (3)
H170.20640.64700.09470.054*
C180.20586 (13)0.77091 (13)0.20118 (12)0.0443 (3)
C190.27809 (16)0.79386 (16)0.28732 (15)0.0641 (4)
H190.37170.73380.31380.077*
C200.21497 (18)0.90297 (17)0.33441 (15)0.0662 (4)
H200.26590.91630.39200.079*
C210.07566 (15)0.99328 (13)0.29641 (12)0.0486 (3)
C220.00317 (14)0.97443 (13)0.20907 (13)0.0490 (3)
H22−0.08961.03550.18150.059*
C230.06918 (13)0.86400 (14)0.16245 (12)0.0473 (3)
H230.01970.85230.10310.057*
C24−0.12136 (18)1.19079 (18)0.31659 (19)0.0738 (5)
H24A−0.19321.13630.33660.089*
H24B−0.12401.23950.23150.089*
H24C−0.14481.25900.35980.089*
U11U22U33U12U13U23
O10.0601 (7)0.0888 (8)0.0657 (7)−0.0011 (6)−0.0250 (5)−0.0010 (6)
O20.0324 (4)0.0461 (5)0.0500 (5)−0.0061 (3)−0.0027 (3)−0.0058 (4)
O30.0375 (5)0.0919 (8)0.0881 (8)−0.0172 (5)−0.0057 (5)−0.0291 (7)
O40.0681 (7)0.0516 (6)0.0810 (7)0.0021 (5)−0.0087 (5)−0.0331 (5)
C10.0391 (6)0.0435 (6)0.0477 (7)−0.0058 (5)−0.0068 (5)−0.0183 (5)
C20.0514 (7)0.0497 (7)0.0486 (7)−0.0032 (6)−0.0126 (6)−0.0166 (6)
C30.0613 (8)0.0545 (8)0.0429 (7)−0.0093 (6)−0.0030 (6)−0.0111 (6)
C40.0473 (7)0.0454 (7)0.0463 (7)−0.0117 (5)0.0010 (5)−0.0123 (5)
C50.0368 (6)0.0444 (7)0.0490 (7)−0.0054 (5)−0.0006 (5)−0.0120 (5)
C60.0385 (6)0.0386 (6)0.0441 (6)−0.0068 (5)−0.0025 (5)−0.0141 (5)
C70.0657 (9)0.0573 (9)0.0751 (10)−0.0215 (7)0.0006 (7)−0.0278 (7)
C80.0572 (9)0.0680 (10)0.0608 (9)−0.0195 (7)0.0102 (7)−0.0090 (7)
C90.0363 (6)0.0461 (7)0.0539 (7)−0.0085 (5)−0.0008 (5)−0.0248 (6)
C100.0391 (7)0.0654 (8)0.0660 (9)−0.0161 (6)0.0009 (6)−0.0332 (7)
C110.0534 (9)0.0766 (10)0.0753 (10)−0.0318 (8)0.0059 (7)−0.0232 (8)
C120.0480 (7)0.0623 (8)0.0571 (8)−0.0193 (6)0.0078 (6)−0.0171 (7)
C130.0450 (7)0.0470 (7)0.0575 (8)−0.0089 (6)0.0049 (6)−0.0138 (6)
C140.0357 (6)0.0432 (6)0.0507 (7)−0.0095 (5)0.0026 (5)−0.0203 (5)
C150.0671 (10)0.0969 (13)0.0628 (10)−0.0153 (9)0.0069 (8)−0.0372 (9)
C160.0777 (12)0.0837 (12)0.0802 (12)−0.0335 (10)0.0134 (9)−0.0029 (10)
C170.0341 (6)0.0495 (7)0.0537 (7)−0.0034 (5)−0.0102 (5)−0.0222 (6)
C180.0347 (6)0.0447 (7)0.0520 (7)−0.0040 (5)−0.0077 (5)−0.0168 (5)
C190.0501 (8)0.0606 (9)0.0794 (10)0.0128 (6)−0.0310 (7)−0.0339 (8)
C200.0646 (9)0.0612 (9)0.0744 (10)0.0057 (7)−0.0304 (8)−0.0341 (8)
C210.0481 (7)0.0390 (6)0.0544 (7)−0.0054 (5)−0.0017 (6)−0.0140 (5)
C220.0335 (6)0.0427 (7)0.0641 (8)−0.0013 (5)−0.0076 (5)−0.0134 (6)
C230.0358 (6)0.0490 (7)0.0563 (7)−0.0060 (5)−0.0113 (5)−0.0167 (6)
C240.0550 (9)0.0597 (9)0.1074 (14)−0.0030 (7)0.0101 (9)−0.0406 (9)
C1—C61.3380 (17)C12—C161.527 (2)
C1—C21.4676 (19)C12—C131.531 (2)
C1—C171.5103 (19)C13—C141.4849 (19)
C2—O11.2149 (17)C13—H13A0.9700
C2—C31.503 (2)C13—H13B0.9700
C3—C41.528 (2)C14—O21.3790 (16)
C3—H3A0.9700C15—H15A0.9600
C3—H3B0.9700C15—H15B0.9600
C4—C71.525 (2)C15—H15C0.9600
C4—C81.529 (2)C16—H16A0.9600
C4—C51.5325 (18)C16—H16B0.9600
C5—C61.4866 (18)C16—H16C0.9600
C5—H5A0.9700C17—C181.5214 (17)
C5—H5B0.9700C17—H170.9800
C6—O21.3779 (15)C18—C231.3756 (17)
C7—H7A0.9600C18—C191.3843 (19)
C7—H7B0.9600C19—C201.370 (2)
C7—H7C0.9600C19—H190.9300
C8—H8A0.9600C20—C211.384 (2)
C8—H8B0.9600C20—H200.9300
C8—H8C0.9600C21—O41.3649 (16)
C9—C141.3373 (18)C21—C221.3749 (19)
C9—C101.4693 (19)C22—C231.3826 (19)
C9—C171.5083 (19)C22—H220.9300
C10—O31.2205 (17)C23—H230.9300
C10—C111.501 (2)C24—O41.4170 (19)
C11—C121.529 (2)C24—H24A0.9600
C11—H11A0.9700C24—H24B0.9600
C11—H11B0.9700C24—H24C0.9600
C12—C151.525 (2)
C6—C1—C2118.25 (12)C16—C12—C13109.43 (13)
C6—C1—C17122.42 (12)C11—C12—C13107.83 (13)
C2—C1—C17119.33 (11)C14—C13—C12112.37 (11)
O1—C2—C1120.64 (14)C14—C13—H13A109.1
O1—C2—C3121.08 (13)C12—C13—H13A109.1
C1—C2—C3118.22 (11)C14—C13—H13B109.1
C2—C3—C4115.16 (12)C12—C13—H13B109.1
C2—C3—H3A108.5H13A—C13—H13B107.9
C4—C3—H3A108.5C9—C14—O2122.76 (12)
C2—C3—H3B108.5C9—C14—C13125.86 (12)
C4—C3—H3B108.5O2—C14—C13111.38 (10)
H3A—C3—H3B107.5C12—C15—H15A109.5
C7—C4—C3110.09 (12)C12—C15—H15B109.5
C7—C4—C8109.28 (12)H15A—C15—H15B109.5
C3—C4—C8110.25 (12)C12—C15—H15C109.5
C7—C4—C5110.58 (12)H15A—C15—H15C109.5
C3—C4—C5107.82 (11)H15B—C15—H15C109.5
C8—C4—C5108.82 (11)C12—C16—H16A109.5
C6—C5—C4112.35 (10)C12—C16—H16B109.5
C6—C5—H5A109.1H16A—C16—H16B109.5
C4—C5—H5A109.1C12—C16—H16C109.5
C6—C5—H5B109.1H16A—C16—H16C109.5
C4—C5—H5B109.1H16B—C16—H16C109.5
H5A—C5—H5B107.9C9—C17—C1108.73 (10)
C1—C6—O2122.58 (11)C9—C17—C18110.10 (11)
C1—C6—C5125.87 (12)C1—C17—C18112.24 (10)
O2—C6—C5111.55 (10)C9—C17—H17108.6
C4—C7—H7A109.5C1—C17—H17108.6
C4—C7—H7B109.5C18—C17—H17108.6
H7A—C7—H7B109.5C23—C18—C19117.39 (12)
C4—C7—H7C109.5C23—C18—C17121.70 (11)
H7A—C7—H7C109.5C19—C18—C17120.88 (11)
H7B—C7—H7C109.5C20—C19—C18121.55 (12)
C4—C8—H8A109.5C20—C19—H19119.2
C4—C8—H8B109.5C18—C19—H19119.2
H8A—C8—H8B109.5C19—C20—C21120.15 (13)
C4—C8—H8C109.5C19—C20—H20119.9
H8A—C8—H8C109.5C21—C20—H20119.9
H8B—C8—H8C109.5O4—C21—C22125.20 (12)
C14—C9—C10118.31 (13)O4—C21—C20115.43 (12)
C14—C9—C17122.32 (11)C22—C21—C20119.34 (12)
C10—C9—C17119.36 (11)C21—C22—C23119.53 (12)
O3—C10—C9120.22 (14)C21—C22—H22120.2
O3—C10—C11121.56 (13)C23—C22—H22120.2
C9—C10—C11118.17 (12)C18—C23—C22122.01 (12)
C10—C11—C12115.00 (12)C18—C23—H23119.0
C10—C11—H11A108.5C22—C23—H23119.0
C12—C11—H11A108.5O4—C24—H24A109.5
C10—C11—H11B108.5O4—C24—H24B109.5
C12—C11—H11B108.5H24A—C24—H24B109.5
H11A—C11—H11B107.5O4—C24—H24C109.5
C15—C12—C16109.43 (15)H24A—C24—H24C109.5
C15—C12—C11110.00 (13)H24B—C24—H24C109.5
C16—C12—C11110.23 (14)C6—O2—C14117.94 (9)
C15—C12—C13109.89 (13)C21—O4—C24117.83 (12)
C6—C1—C2—O1173.50 (13)C10—C9—C14—C13−3.52 (19)
C17—C1—C2—O1−6.3 (2)C17—C9—C14—C13175.26 (12)
C6—C1—C2—C3−3.61 (18)C12—C13—C14—C9−23.36 (19)
C17—C1—C2—C3176.58 (11)C12—C13—C14—O2157.27 (11)
O1—C2—C3—C4156.50 (14)C14—C9—C17—C117.55 (16)
C1—C2—C3—C4−26.40 (18)C10—C9—C17—C1−163.68 (10)
C2—C3—C4—C7−69.32 (16)C14—C9—C17—C18−105.79 (13)
C2—C3—C4—C8170.04 (12)C10—C9—C17—C1872.98 (14)
C2—C3—C4—C551.38 (15)C6—C1—C17—C9−17.61 (16)
C7—C4—C5—C672.00 (14)C2—C1—C17—C9162.18 (11)
C3—C4—C5—C6−48.39 (14)C6—C1—C17—C18104.44 (14)
C8—C4—C5—C6−167.96 (12)C2—C1—C17—C18−75.76 (14)
C2—C1—C6—O2−174.28 (11)C9—C17—C18—C23−116.51 (13)
C17—C1—C6—O25.52 (18)C1—C17—C18—C23122.23 (13)
C2—C1—C6—C55.41 (19)C9—C17—C18—C1961.45 (17)
C17—C1—C6—C5−174.79 (11)C1—C17—C18—C19−59.82 (17)
C4—C5—C6—C122.49 (18)C23—C18—C19—C201.4 (2)
C4—C5—C6—O2−157.79 (10)C17—C18—C19—C20−176.62 (16)
C14—C9—C10—O3−175.89 (13)C18—C19—C20—C210.2 (3)
C17—C9—C10—O35.29 (19)C19—C20—C21—O4−179.83 (16)
C14—C9—C10—C111.51 (18)C19—C20—C21—C22−1.5 (2)
C17—C9—C10—C11−177.32 (12)O4—C21—C22—C23179.39 (13)
O3—C10—C11—C12−154.88 (14)C20—C21—C22—C231.3 (2)
C9—C10—C11—C1227.76 (19)C19—C18—C23—C22−1.7 (2)
C10—C11—C12—C1568.08 (18)C17—C18—C23—C22176.34 (13)
C10—C11—C12—C16−171.16 (14)C21—C22—C23—C180.3 (2)
C10—C11—C12—C13−51.75 (17)C1—C6—O2—C149.04 (17)
C15—C12—C13—C14−71.43 (16)C5—C6—O2—C14−170.69 (10)
C16—C12—C13—C14168.39 (13)C9—C14—O2—C6−9.10 (17)
C11—C12—C13—C1448.47 (16)C13—C14—O2—C6170.29 (10)
C10—C9—C14—O2175.78 (11)C22—C21—O4—C244.2 (2)
C17—C9—C14—O2−5.43 (18)C20—C21—O4—C24−177.63 (15)
D—H···AD—HH···AD···AD—H···A
C11—H11A···O4i0.972.573.364 (2)139
C15—H15C···O3ii0.962.583.506 (2)161
C22—H22···O1iii0.932.423.343 (2)171
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C11—H11A⋯O4i0.972.573.364 (2)139
C15—H15C⋯O3ii0.962.583.506 (2)161
C22—H22⋯O1iii0.932.423.343 (2)171

Symmetry codes: (i) ; (ii) ; (iii) .

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3.  Chemical aspects of santalin as a histological stain.

Authors:  A Banerjee; A K Mukherjee
Journal:  Stain Technol       Date:  1981-03
  3 in total
  7 in total

1.  Dimethyl-ammonium 5,5-dimethyl-3-oxo-2-(3,3,6,6-tetra-methyl-1,8-dioxo-2,3,4,5,6,7,8,9-octa-hydro-1H-xanthen-9-yl)cyclo-hex-1-enolate 9-(2-hydr-oxy-4,4-dimethyl-6-oxocyclo-hex-1-en-yl)-3,3,6,6-tetra-methyl-3,4,5,6,7,9-hexa-hydro-1H-xanthene-1,8(2H)-dione n-hexane hemisolvate monohydrate.

Authors:  Noorhafizah Hasanudin; Aisyah Saad Abdul Rahim; Salizawati Muhamad Salhimi; Jia Hao Goh; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-01-30

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

Authors:  Hao Shi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-11-17

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

Authors:  Hoong-Kun Fun; Wan-Sin Loh; K Rajesh; V Vijayakumar; S Sarveswari
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-07-02

4.  2,2'-[(3-Bromo-4-hy-droxy-5-meth-oxy-phen-yl)methyl-idene]bis-(3-hy-droxy-5,5-dimethyl-cyclo-hex-2-en-1-one).

Authors:  V Sughanya; N Sureshbabu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-09-08

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

Authors:  N Sureshbabu; V Sughanya
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-01-23

6.  2,2'-[(4-Eth-oxy-phen-yl)methyl-ene]bis-(3-hy-droxy-5,5-dimethyl-cyclo-hex-2-en-1-one).

Authors:  N Sureshbabu; V Sughanya
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-08-04

7.  9-(4-Hy-droxy-3,5-dimeth-oxy-phen-yl)-3,3,6,6-tetra-methyl-3,4,5,6,7,9-hexa-hydro-1H-xanthene-1,8(2H)-dione.

Authors:  V Sughanya; N Sureshbabu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-03-14
  7 in total

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