9-(4-Methoxy­phen­yl)-3,3,6,6-tetra­methyl-3,4,6,7-tetra­hydro-2H-xanthene-1,8(5H,9H)-dione

Odabaşoğlu, M.; Kaya, M.; Yıldırır, Y.; Büyükgüngör, O.

doi:10.1107/S160053680800603X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o681

doi:10.1107/S160053680800603X

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9-(4-Methoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7-tetrahydro-2H-xanthene-1,8(5H,9H)-dione

Mustafa Odabaşoğlu,^a Muharrem Kaya,^b Yılmaz Yıldırır ^c and Orhan Büyükgüngör ^d ^*

^aDepartment of Chemistry, Faculty of Arts & Science, Ondokuz Mayıs University, TR-55139 Kurupelit Samsun, Turkey, ^bDepartment of Chemistry, Faculty of Arts & Science, Dumlupınar University, Kütahya, Turkey, ^cDepartment of Chemistry, Faculty of Arts & Science, Gazi University, Ankara, Turkey, and ^dDepartment of Physics, Faculty of Arts & Science, Ondokuz Mayıs University, TR-55139 Kurupelit Samsun, Turkey
^*Correspondence e-mail: orhanb@omu.edu.tr

(Received 29 February 2008; accepted 4 March 2008; online 7 March 2008)

In the molecule of the title compound, C₂₄H₂₈O₄, 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 molecules, generating centrosymmetric R₂²(12), R₄⁴(28) and R₂²(16) ring motifs and forming a three-dimensional network.

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_r = 380.46
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.108
S = 1.04
4035 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O4ⁱ	0.97	2.57	3.364 (2)	139
C15—H15C⋯O3ⁱⁱ	0.96	2.58	3.506 (2)	161
C22—H22⋯O1ⁱⁱⁱ	0.93	2.42	3.343 (2)	171
Symmetry codes: (i) x, y-1, z; (ii) -x, -y+1, -z+1; (iii) -x, -y+2, -z.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680800603X/hk2429sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680800603X/hk2429Isup2.hkl

checkCIF report

Comment top

Xanthenes are an important class of organic compounds that find use as dyes, fluorescent materials for visualization of biomolecules and in laser technologies, due to their useful spectroscopic properties (Menchen et al., 2003; Banerjee & Mukherjee, 1981). Oxidation of these compounds can be converted to the corresponding xanthylium salts, which are also effective as dyes and fluorescent materials (Nogradi, 2003; Kamel & Shoeb, 1964). Xanthenes have also received considerable attention from many pharmaceuticals and organic chemists, actually because of the broad spectrum of their biological and pharmaceutical properties such as agricultural bactericide effects (Hideo, 1981), photodynamic therapy, anti-inflammatory activities (Poupelin et al., 1978) and antiviral effects (Lambert et al., 1997). In view of the importance of the title compound, (I), we report herein its crystal structure.

In the molecule of (I), (Fig. 1), rings A (C1—C6), B (C1/C6/O2/C13/C14/C17) and C (C9—C14) are not planar, having total puckering amplitudes, Q_T, of 0.463 (3), 0.194 (3) and 0.459 (2) Å, respectively. They adopt envelope [ϕ = -2.43 (2)° and θ = 121.76 (3)°], boat [ϕ = 139.80 (3)° and θ = 88.77 (3)°] and envelope [ϕ = 176.89 (4)° and θ = 56.53 (3)°] conformations (Cremer & Pople, 1975). In rings A and C, atoms C4 and C12 displaced by -0.645 (3) and -0.641 (4) Å from the plane of the other ring atoms, respectively. Ring D (C18—C23) is, of course, planar.

In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 1) link the molecules, generating centrosymmetric R₂²(12), R₄⁴(28) (Fig. 2) and R₂²(16) (Fig. 3) ring motifs (Bernstein et al., 1995; Etter, 1990), to form a three-dimensional network, in which they may be effective in the stabilization of the structure.

Related literature top

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 top

The syntheses of 2,2'-[(4-methoxyphenyl)methylene]bis(5,5-dimethylcyclohexane- 1,3-dione), (II), was achieved according to the procedure described in the literature (Horning & Horning, 1946). A mixture of (II) (5 mmol) and acetic acid (20 ml) was refluxed for 2 h. The reaction mixture was concentrated under reduced pressure and poured into crushed ice. The solid obtained was filtered off, dried and crystallized from EtOH-H₂O (8:2) (yield: 92%, m.p. 515–517 K).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); 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).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A partial packing diagram of (I), showing the formation of R₂²(12) and R₄⁴(28) ring motifs. Hydrogen bonds are shown as dashed lines [symmetry codes: (i) x, 2 - y, z; (ii) -x, 1 - y, 1 - z]. H atoms not involved in hydrogen bondings have been omitted for clarity.
	Fig. 3. A packing diagram of (I). Hydrogen bonds are shown as dashed lines [symmetry codes: (i) -x, 1 - y, 1 - z; (ii) x + 1, y, z; (iii) x + 1, y + 1, z; (iv) -x, 2 - y, 1 - z; (v) x, y, z + 1]. H atoms not involved in hydrogen bondings have been omitted for clarity.

9-(4-Methoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7-tetrahydro-2H-xanthene- 1,8(5H,9H)-dione top

Crystal data top

C₂₄H₂₈O₄	Z = 2
M_r = 380.46	F(000) = 408
Triclinic, P1	D_x = 1.232 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.346 (5) Å	Cell parameters from 17059 reflections
b = 10.314 (5) Å	θ = 1.8–28.0°
c = 11.733 (5) Å	µ = 0.08 mm⁻¹
α = 71.089 (5)°	T = 296 K
β = 84.253 (5)°	Prism, colorless
γ = 73.386 (5)°	0.66 × 0.54 × 0.41 mm
V = 1025.2 (9) Å³

Data collection top

Stoe IPDSII diffractometer	4035 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3450 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.033
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 2.2°
ω–scan rotation method	h = −11→11
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→12
T_min = 0.947, T_max = 0.975	l = −14→14
17059 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0512P)² + 0.165P] where P = (F_o² + 2F_c²)/3
4035 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₄H₂₈O₄	γ = 73.386 (5)°
M_r = 380.46	V = 1025.2 (9) Å³
Triclinic, P1	Z = 2
a = 9.346 (5) Å	Mo Kα radiation
b = 10.314 (5) Å	µ = 0.08 mm⁻¹
c = 11.733 (5) Å	T = 296 K
α = 71.089 (5)°	0.66 × 0.54 × 0.41 mm
β = 84.253 (5)°

Data collection top

Stoe IPDSII diffractometer	4035 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	3450 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.975	R_int = 0.033
17059 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.04	Δρ_max = 0.16 e Å⁻³
4035 reflections	Δρ_min = −0.17 e Å⁻³
253 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 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.32183 (13)	0.81707 (14)	−0.08171 (10)	0.0796 (4)
O2	0.55478 (9)	0.45682 (9)	0.26047 (8)	0.0459 (2)
O3	0.03418 (11)	0.52647 (13)	0.26037 (11)	0.0718 (3)
O4	0.02323 (12)	1.09853 (11)	0.34873 (10)	0.0672 (3)
C1	0.42493 (13)	0.64720 (13)	0.09685 (11)	0.0431 (3)
C2	0.43421 (15)	0.74638 (14)	−0.02413 (12)	0.0509 (3)
C3	0.58637 (16)	0.75273 (16)	−0.07685 (12)	0.0551 (3)
H3A	0.5799	0.8491	−0.1285	0.066*
H3B	0.6149	0.6909	−0.1271	0.066*
C4	0.70957 (15)	0.70997 (14)	0.01517 (12)	0.0471 (3)
C5	0.70551 (13)	0.56537 (13)	0.10549 (12)	0.0452 (3)
H5A	0.7443	0.4921	0.0669	0.054*
H5B	0.7699	0.5444	0.1727	0.054*
C6	0.55218 (13)	0.56175 (12)	0.15160 (11)	0.0407 (3)
C7	0.68441 (19)	0.82180 (16)	0.07936 (15)	0.0632 (4)
H7A	0.7614	0.7933	0.1378	0.076*
H7B	0.5888	0.8309	0.1191	0.076*
H7C	0.6872	0.9116	0.0215	0.076*
C8	0.86223 (17)	0.69525 (18)	−0.04741 (15)	0.0649 (4)
H8A	0.8782	0.6252	−0.0882	0.078*
H8B	0.9388	0.6662	0.0115	0.078*
H8C	0.8656	0.7851	−0.1048	0.078*
C9	0.28957 (13)	0.50728 (13)	0.25682 (12)	0.0436 (3)
C10	0.15563 (14)	0.46043 (16)	0.30671 (13)	0.0532 (3)
C11	0.17414 (17)	0.32686 (18)	0.41176 (15)	0.0659 (4)
H11A	0.1844	0.2477	0.3813	0.079*
H11B	0.0839	0.3353	0.4606	0.079*
C12	0.30751 (16)	0.29219 (16)	0.49231 (13)	0.0558 (3)
C13	0.44636 (15)	0.29653 (14)	0.41151 (13)	0.0516 (3)
H13A	0.5285	0.2921	0.4583	0.062*
H13B	0.4743	0.2136	0.3838	0.062*
C14	0.42175 (13)	0.42701 (13)	0.30557 (11)	0.0422 (3)
C15	0.2821 (2)	0.4017 (2)	0.55902 (16)	0.0745 (5)
H15A	0.2686	0.4950	0.5017	0.089*
H15B	0.3672	0.3802	0.6082	0.089*
H15C	0.1946	0.3988	0.6091	0.089*
C16	0.3294 (2)	0.1439 (2)	0.58349 (18)	0.0846 (6)
H16A	0.4154	0.1220	0.6317	0.102*
H16B	0.3438	0.0751	0.5416	0.102*
H16C	0.2426	0.1413	0.6345	0.102*
C17	0.27361 (13)	0.64451 (13)	0.15483 (12)	0.0452 (3)
H17	0.2064	0.6470	0.0947	0.054*
C18	0.20586 (13)	0.77091 (13)	0.20118 (12)	0.0443 (3)
C19	0.27809 (16)	0.79386 (16)	0.28732 (15)	0.0641 (4)
H19	0.3717	0.7338	0.3138	0.077*
C20	0.21497 (18)	0.90297 (17)	0.33441 (15)	0.0662 (4)
H20	0.2659	0.9163	0.3920	0.079*
C21	0.07566 (15)	0.99328 (13)	0.29641 (12)	0.0486 (3)
C22	0.00317 (14)	0.97443 (13)	0.20907 (13)	0.0490 (3)
H22	−0.0896	1.0355	0.1815	0.059*
C23	0.06918 (13)	0.86400 (14)	0.16245 (12)	0.0473 (3)
H23	0.0197	0.8523	0.1031	0.057*
C24	−0.12136 (18)	1.19079 (18)	0.31659 (19)	0.0738 (5)
H24A	−0.1932	1.1363	0.3366	0.089*
H24B	−0.1240	1.2395	0.2315	0.089*
H24C	−0.1448	1.2590	0.3598	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0601 (7)	0.0888 (8)	0.0657 (7)	−0.0011 (6)	−0.0250 (5)	−0.0010 (6)
O2	0.0324 (4)	0.0461 (5)	0.0500 (5)	−0.0061 (3)	−0.0027 (3)	−0.0058 (4)
O3	0.0375 (5)	0.0919 (8)	0.0881 (8)	−0.0172 (5)	−0.0057 (5)	−0.0291 (7)
O4	0.0681 (7)	0.0516 (6)	0.0810 (7)	0.0021 (5)	−0.0087 (5)	−0.0331 (5)
C1	0.0391 (6)	0.0435 (6)	0.0477 (7)	−0.0058 (5)	−0.0068 (5)	−0.0183 (5)
C2	0.0514 (7)	0.0497 (7)	0.0486 (7)	−0.0032 (6)	−0.0126 (6)	−0.0166 (6)
C3	0.0613 (8)	0.0545 (8)	0.0429 (7)	−0.0093 (6)	−0.0030 (6)	−0.0111 (6)
C4	0.0473 (7)	0.0454 (7)	0.0463 (7)	−0.0117 (5)	0.0010 (5)	−0.0123 (5)
C5	0.0368 (6)	0.0444 (7)	0.0490 (7)	−0.0054 (5)	−0.0006 (5)	−0.0120 (5)
C6	0.0385 (6)	0.0386 (6)	0.0441 (6)	−0.0068 (5)	−0.0025 (5)	−0.0141 (5)
C7	0.0657 (9)	0.0573 (9)	0.0751 (10)	−0.0215 (7)	0.0006 (7)	−0.0278 (7)
C8	0.0572 (9)	0.0680 (10)	0.0608 (9)	−0.0195 (7)	0.0102 (7)	−0.0090 (7)
C9	0.0363 (6)	0.0461 (7)	0.0539 (7)	−0.0085 (5)	−0.0008 (5)	−0.0248 (6)
C10	0.0391 (7)	0.0654 (8)	0.0660 (9)	−0.0161 (6)	0.0009 (6)	−0.0332 (7)
C11	0.0534 (9)	0.0766 (10)	0.0753 (10)	−0.0318 (8)	0.0059 (7)	−0.0232 (8)
C12	0.0480 (7)	0.0623 (8)	0.0571 (8)	−0.0193 (6)	0.0078 (6)	−0.0171 (7)
C13	0.0450 (7)	0.0470 (7)	0.0575 (8)	−0.0089 (6)	0.0049 (6)	−0.0138 (6)
C14	0.0357 (6)	0.0432 (6)	0.0507 (7)	−0.0095 (5)	0.0026 (5)	−0.0203 (5)
C15	0.0671 (10)	0.0969 (13)	0.0628 (10)	−0.0153 (9)	0.0069 (8)	−0.0372 (9)
C16	0.0777 (12)	0.0837 (12)	0.0802 (12)	−0.0335 (10)	0.0134 (9)	−0.0029 (10)
C17	0.0341 (6)	0.0495 (7)	0.0537 (7)	−0.0034 (5)	−0.0102 (5)	−0.0222 (6)
C18	0.0347 (6)	0.0447 (7)	0.0520 (7)	−0.0040 (5)	−0.0077 (5)	−0.0168 (5)
C19	0.0501 (8)	0.0606 (9)	0.0794 (10)	0.0128 (6)	−0.0310 (7)	−0.0339 (8)
C20	0.0646 (9)	0.0612 (9)	0.0744 (10)	0.0057 (7)	−0.0304 (8)	−0.0341 (8)
C21	0.0481 (7)	0.0390 (6)	0.0544 (7)	−0.0054 (5)	−0.0017 (6)	−0.0140 (5)
C22	0.0335 (6)	0.0427 (7)	0.0641 (8)	−0.0013 (5)	−0.0076 (5)	−0.0134 (6)
C23	0.0358 (6)	0.0490 (7)	0.0563 (7)	−0.0060 (5)	−0.0113 (5)	−0.0167 (6)
C24	0.0550 (9)	0.0597 (9)	0.1074 (14)	−0.0030 (7)	0.0101 (9)	−0.0406 (9)

Geometric parameters (Å, º) top

C1—C6	1.3380 (17)	C12—C16	1.527 (2)
C1—C2	1.4676 (19)	C12—C13	1.531 (2)
C1—C17	1.5103 (19)	C13—C14	1.4849 (19)
C2—O1	1.2149 (17)	C13—H13A	0.9700
C2—C3	1.503 (2)	C13—H13B	0.9700
C3—C4	1.528 (2)	C14—O2	1.3790 (16)
C3—H3A	0.9700	C15—H15A	0.9600
C3—H3B	0.9700	C15—H15B	0.9600
C4—C7	1.525 (2)	C15—H15C	0.9600
C4—C8	1.529 (2)	C16—H16A	0.9600
C4—C5	1.5325 (18)	C16—H16B	0.9600
C5—C6	1.4866 (18)	C16—H16C	0.9600
C5—H5A	0.9700	C17—C18	1.5214 (17)
C5—H5B	0.9700	C17—H17	0.9800
C6—O2	1.3779 (15)	C18—C23	1.3756 (17)
C7—H7A	0.9600	C18—C19	1.3843 (19)
C7—H7B	0.9600	C19—C20	1.370 (2)
C7—H7C	0.9600	C19—H19	0.9300
C8—H8A	0.9600	C20—C21	1.384 (2)
C8—H8B	0.9600	C20—H20	0.9300
C8—H8C	0.9600	C21—O4	1.3649 (16)
C9—C14	1.3373 (18)	C21—C22	1.3749 (19)
C9—C10	1.4693 (19)	C22—C23	1.3826 (19)
C9—C17	1.5083 (19)	C22—H22	0.9300
C10—O3	1.2205 (17)	C23—H23	0.9300
C10—C11	1.501 (2)	C24—O4	1.4170 (19)
C11—C12	1.529 (2)	C24—H24A	0.9600
C11—H11A	0.9700	C24—H24B	0.9600
C11—H11B	0.9700	C24—H24C	0.9600
C12—C15	1.525 (2)

C6—C1—C2	118.25 (12)	C16—C12—C13	109.43 (13)
C6—C1—C17	122.42 (12)	C11—C12—C13	107.83 (13)
C2—C1—C17	119.33 (11)	C14—C13—C12	112.37 (11)
O1—C2—C1	120.64 (14)	C14—C13—H13A	109.1
O1—C2—C3	121.08 (13)	C12—C13—H13A	109.1
C1—C2—C3	118.22 (11)	C14—C13—H13B	109.1
C2—C3—C4	115.16 (12)	C12—C13—H13B	109.1
C2—C3—H3A	108.5	H13A—C13—H13B	107.9
C4—C3—H3A	108.5	C9—C14—O2	122.76 (12)
C2—C3—H3B	108.5	C9—C14—C13	125.86 (12)
C4—C3—H3B	108.5	O2—C14—C13	111.38 (10)
H3A—C3—H3B	107.5	C12—C15—H15A	109.5
C7—C4—C3	110.09 (12)	C12—C15—H15B	109.5
C7—C4—C8	109.28 (12)	H15A—C15—H15B	109.5
C3—C4—C8	110.25 (12)	C12—C15—H15C	109.5
C7—C4—C5	110.58 (12)	H15A—C15—H15C	109.5
C3—C4—C5	107.82 (11)	H15B—C15—H15C	109.5
C8—C4—C5	108.82 (11)	C12—C16—H16A	109.5
C6—C5—C4	112.35 (10)	C12—C16—H16B	109.5
C6—C5—H5A	109.1	H16A—C16—H16B	109.5
C4—C5—H5A	109.1	C12—C16—H16C	109.5
C6—C5—H5B	109.1	H16A—C16—H16C	109.5
C4—C5—H5B	109.1	H16B—C16—H16C	109.5
H5A—C5—H5B	107.9	C9—C17—C1	108.73 (10)
C1—C6—O2	122.58 (11)	C9—C17—C18	110.10 (11)
C1—C6—C5	125.87 (12)	C1—C17—C18	112.24 (10)
O2—C6—C5	111.55 (10)	C9—C17—H17	108.6
C4—C7—H7A	109.5	C1—C17—H17	108.6
C4—C7—H7B	109.5	C18—C17—H17	108.6
H7A—C7—H7B	109.5	C23—C18—C19	117.39 (12)
C4—C7—H7C	109.5	C23—C18—C17	121.70 (11)
H7A—C7—H7C	109.5	C19—C18—C17	120.88 (11)
H7B—C7—H7C	109.5	C20—C19—C18	121.55 (12)
C4—C8—H8A	109.5	C20—C19—H19	119.2
C4—C8—H8B	109.5	C18—C19—H19	119.2
H8A—C8—H8B	109.5	C19—C20—C21	120.15 (13)
C4—C8—H8C	109.5	C19—C20—H20	119.9
H8A—C8—H8C	109.5	C21—C20—H20	119.9
H8B—C8—H8C	109.5	O4—C21—C22	125.20 (12)
C14—C9—C10	118.31 (13)	O4—C21—C20	115.43 (12)
C14—C9—C17	122.32 (11)	C22—C21—C20	119.34 (12)
C10—C9—C17	119.36 (11)	C21—C22—C23	119.53 (12)
O3—C10—C9	120.22 (14)	C21—C22—H22	120.2
O3—C10—C11	121.56 (13)	C23—C22—H22	120.2
C9—C10—C11	118.17 (12)	C18—C23—C22	122.01 (12)
C10—C11—C12	115.00 (12)	C18—C23—H23	119.0
C10—C11—H11A	108.5	C22—C23—H23	119.0
C12—C11—H11A	108.5	O4—C24—H24A	109.5
C10—C11—H11B	108.5	O4—C24—H24B	109.5
C12—C11—H11B	108.5	H24A—C24—H24B	109.5
H11A—C11—H11B	107.5	O4—C24—H24C	109.5
C15—C12—C16	109.43 (15)	H24A—C24—H24C	109.5
C15—C12—C11	110.00 (13)	H24B—C24—H24C	109.5
C16—C12—C11	110.23 (14)	C6—O2—C14	117.94 (9)
C15—C12—C13	109.89 (13)	C21—O4—C24	117.83 (12)

C6—C1—C2—O1	173.50 (13)	C10—C9—C14—C13	−3.52 (19)
C17—C1—C2—O1	−6.3 (2)	C17—C9—C14—C13	175.26 (12)
C6—C1—C2—C3	−3.61 (18)	C12—C13—C14—C9	−23.36 (19)
C17—C1—C2—C3	176.58 (11)	C12—C13—C14—O2	157.27 (11)
O1—C2—C3—C4	156.50 (14)	C14—C9—C17—C1	17.55 (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—C8	170.04 (12)	C10—C9—C17—C18	72.98 (14)
C2—C3—C4—C5	51.38 (15)	C6—C1—C17—C9	−17.61 (16)
C7—C4—C5—C6	72.00 (14)	C2—C1—C17—C9	162.18 (11)
C3—C4—C5—C6	−48.39 (14)	C6—C1—C17—C18	104.44 (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—O2	5.52 (18)	C1—C17—C18—C23	122.23 (13)
C2—C1—C6—C5	5.41 (19)	C9—C17—C18—C19	61.45 (17)
C17—C1—C6—C5	−174.79 (11)	C1—C17—C18—C19	−59.82 (17)
C4—C5—C6—C1	22.49 (18)	C23—C18—C19—C20	1.4 (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—C21	0.2 (3)
C17—C9—C10—O3	5.29 (19)	C19—C20—C21—O4	−179.83 (16)
C14—C9—C10—C11	1.51 (18)	C19—C20—C21—C22	−1.5 (2)
C17—C9—C10—C11	−177.32 (12)	O4—C21—C22—C23	179.39 (13)
O3—C10—C11—C12	−154.88 (14)	C20—C21—C22—C23	1.3 (2)
C9—C10—C11—C12	27.76 (19)	C19—C18—C23—C22	−1.7 (2)
C10—C11—C12—C15	68.08 (18)	C17—C18—C23—C22	176.34 (13)
C10—C11—C12—C16	−171.16 (14)	C21—C22—C23—C18	0.3 (2)
C10—C11—C12—C13	−51.75 (17)	C1—C6—O2—C14	9.04 (17)
C15—C12—C13—C14	−71.43 (16)	C5—C6—O2—C14	−170.69 (10)
C16—C12—C13—C14	168.39 (13)	C9—C14—O2—C6	−9.10 (17)
C11—C12—C13—C14	48.47 (16)	C13—C14—O2—C6	170.29 (10)
C10—C9—C14—O2	175.78 (11)	C22—C21—O4—C24	4.2 (2)
C17—C9—C14—O2	−5.43 (18)	C20—C21—O4—C24	−177.63 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O4ⁱ	0.97	2.57	3.364 (2)	139
C15—H15C···O3ⁱⁱ	0.96	2.58	3.506 (2)	161
C22—H22···O1ⁱⁱⁱ	0.93	2.42	3.343 (2)	171

Symmetry codes: (i) x, y−1, z; (ii) −x, −y+1, −z+1; (iii) −x, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₈O₄
M_r	380.46
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.346 (5), 10.314 (5), 11.733 (5)
α, β, γ (°)	71.089 (5), 84.253 (5), 73.386 (5)
V (Å³)	1025.2 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.66 × 0.54 × 0.41

Data collection
Diffractometer	Stoe IPDSII diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.947, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	17059, 4035, 3450
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.109, 1.04
No. of reflections	4035
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.17

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O4ⁱ	0.97	2.57	3.364 (2)	139.2
C15—H15C···O3ⁱⁱ	0.96	2.58	3.506 (2)	160.9
C22—H22···O1ⁱⁱⁱ	0.93	2.42	3.343 (2)	171.0

Symmetry codes: (i) x, y−1, z; (ii) −x, −y+1, −z+1; (iii) −x, −y+2, −z.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant F.279 of the University Research Fund).

References

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Poupelin, J. P., Saint-Rut, G., Foussard-Blanpin, O., Narcisse, G., Uchida- Ernouf, G. & Lacroix, R. (1978). Eur. J. Med. Chem. 13, 67–71. CAS Google Scholar
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Volume 64| Part 4| April 2008| Page o681

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

9-(4-Meth­oxy­phen­yl)-3,3,6,6-tetra­methyl-3,4,6,7-tetra­hydro-2H-xanthene-1,8(5H,9H)-dione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

9-(4-Methoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7-tetrahydro-2H-xanthene-1,8(5H,9H)-dione