9-(7-Fluoro-4-oxo-4H-chromen-3-yl)-3,3,6,6-tetra­methyl-2,3,4,5,6,7,8,9-octa­hydro-1H-xanthene-1,8-dione

Asad, M.; Oo, C.-W.; Osman, H.; Fun, H.-K.; Arshad, S.

doi:10.1107/S1600536811051749

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o38

doi:10.1107/S1600536811051749

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9-(7-Fluoro-4-oxo-4H-chromen-3-yl)-3,3,6,6-tetramethyl-2,3,4,5,6,7,8,9-octahydro-1H-xanthene-1,8-dione

Mohammad Asad,^a Chuan-Wei Oo,^a ‡ Hasnah Osman,^a Hoong-Kun Fun ^b ^*§ and Suhana Arshad ^b

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 25 November 2011; accepted 1 December 2011; online 7 December 2011)

In the title compound, C₂₆H₂₅FO₅, the terminal cyclohexane rings of the xanthene ring system adopt half-boat conformations. The 4H-chromene ring make a dihedral angle of 87.94 (5)° with the xanthene ring system and its carbonyl O atom lies above the xanthene O atom. In the crystal, molecules are linked into ribbons propagating along the a-axis direction by C—H⋯O hydrogen bonds. Aromatic π–π stacking interactions [centroid–centroid distance = 3.7367 (12) Å] also occur.

Related literature

For a related structure and background to the properties and applications of xanthene derivatives, see: Mehdi et al. (2011 ). For ring conformations, see: Cremer & Pople (1975 ). For reference bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₆H₂₅FO₅
M_r = 436.46
Monoclinic, P 2₁ /c
a = 6.9475 (8) Å
b = 18.596 (2) Å
c = 17.559 (2) Å
β = 93.658 (2)°
V = 2264.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.51 × 0.38 × 0.24 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.954, T_max = 0.978
21143 measured reflections
6574 independent reflections
4315 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.150
S = 1.03
6574 reflections
293 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15B⋯O4ⁱ	0.97	2.44	3.3487 (19)	156
C18—H18A⋯O5ⁱ	0.97	2.45	3.3821 (19)	162
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811051749/hb6535sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811051749/hb6535Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811051749/hb6535Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of xanthene derivatives (Mehdi et al., 2011), we now describe the synthesis and structure of the title compound, (I).

In the molecular structure, (Fig. 1), the terminal cyclohexane rings (C11–C16 & C17–C22) of the xanthene ring system adopt half boat conformations with puckering parameters Q= 0.4688 (18) Å, Θ= 124.2 (2)°, ϕ= 348.2 (3)° and Q= 0.4638 (17) Å, Θ= 54.8 (2)°, ϕ= 129.1 (2)° (Cremer & Pople, 1975), respectively. The 4H-chromene ring (O1/C1–C9) is approximately perpendicular to the xanthene ring system (O2/C10–C22) with dihedral angle of 87.94 (5)°. Bond lengths (Allen et al., 1987) and angles are within normal ranges and comparable to a related structure (Mehdi et al., 2011).

The crystal packing is shown in Fig. 2. The molecules are linked into ribbons along the a axis via intermolecular C15—H15B···O4 and C18—H18A···O5 hydrogen bonds (Table 1). π–π interactions of Cg1···Cg1 = 3.7367 (12) Å [Cg1 is the centroid of the benzene ring (C2–C7); symmetry code: -x, 1 - y, 2 - z] further stabilized the structure.

Related literature top

For a related structure and background to the properties and applications of xanthene derivatives, see: Mehdi et al. (2011). For ring conformations, see: Cremer & Pople (1975). For reference bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of 7-fluoro-3-formylchromone (2.60 mmol, 0.50 g) and dimedone (5.20 mmol, 0.73 g) in 30 ml methanol was stirred at room temperature overnight. The reaction progress was monitored by TLC. After the reaction was completed, the precipitate obtained was filtered, washed with methanol and dried. The isolated product was further purified by recrystallization from chloroform-methanol (1:1 v/v) to give the pure title compounds as colorless blocks in 92% yield.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

9-(7-Fluoro-4-oxo-4H-chromen-3-yl)-3,3,6,6-tetramethyl- 2,3,4,5,6,7,8,9-octahydro-1H-xanthene-1,8-dione top

Crystal data top

C₂₆H₂₅FO₅	F(000) = 920
M_r = 436.46	D_x = 1.281 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5340 reflections
a = 6.9475 (8) Å	θ = 2.5–29.3°
b = 18.596 (2) Å	µ = 0.09 mm⁻¹
c = 17.559 (2) Å	T = 296 K
β = 93.658 (2)°	Block, colourless
V = 2264.0 (5) Å³	0.51 × 0.38 × 0.24 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	6574 independent reflections
Radiation source: fine-focus sealed tube	4315 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 30.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
T_min = 0.954, T_max = 0.978	k = −24→26
21143 measured reflections	l = −24→24

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0621P)² + 0.5163P] where P = (F_o² + 2F_c²)/3
6574 reflections	(Δ/σ)_max = 0.001
293 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₆H₂₅FO₅	V = 2264.0 (5) Å³
M_r = 436.46	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.9475 (8) Å	µ = 0.09 mm⁻¹
b = 18.596 (2) Å	T = 296 K
c = 17.559 (2) Å	0.51 × 0.38 × 0.24 mm
β = 93.658 (2)°

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	6574 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4315 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.978	R_int = 0.034
21143 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
6574 reflections	Δρ_min = −0.22 e Å⁻³
293 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
F1	0.0382 (3)	0.36000 (10)	1.08974 (8)	0.1100 (6)
O1	−0.25037 (17)	0.46251 (7)	0.86767 (7)	0.0562 (3)
O2	0.29558 (13)	0.54942 (6)	0.61824 (6)	0.0400 (2)
O3	0.26966 (16)	0.48699 (8)	0.77520 (7)	0.0599 (4)
O4	−0.21687 (16)	0.66244 (8)	0.73490 (8)	0.0624 (4)
O5	−0.25611 (16)	0.40218 (7)	0.62320 (8)	0.0626 (4)
C1	−0.2364 (2)	0.48941 (9)	0.79629 (10)	0.0467 (4)
H1A	−0.3502	0.5028	0.7692	0.056*
C2	−0.0864 (3)	0.43986 (9)	0.90721 (10)	0.0491 (4)
C3	−0.1071 (3)	0.41034 (11)	0.97924 (11)	0.0654 (5)
H3A	−0.2278	0.4060	0.9988	0.079*
C4	0.0547 (4)	0.38826 (12)	1.01969 (12)	0.0713 (6)
C5	0.2370 (4)	0.39369 (13)	0.99353 (12)	0.0735 (6)
H5A	0.3447	0.3783	1.0233	0.088*
C6	0.2552 (3)	0.42249 (11)	0.92207 (11)	0.0612 (5)
H6A	0.3768	0.4260	0.9031	0.073*
C7	0.0939 (2)	0.44652 (9)	0.87767 (9)	0.0462 (4)
C8	0.1115 (2)	0.47825 (9)	0.80182 (9)	0.0438 (4)
C9	−0.0704 (2)	0.49818 (9)	0.76172 (9)	0.0402 (3)
C10	−0.07496 (19)	0.52939 (8)	0.68162 (8)	0.0384 (3)
H10A	−0.2097	0.5382	0.6642	0.046*
C11	0.03248 (19)	0.59992 (8)	0.68064 (8)	0.0379 (3)
C12	−0.0564 (2)	0.66493 (9)	0.71072 (9)	0.0444 (4)
C13	0.0533 (2)	0.73440 (10)	0.70679 (12)	0.0560 (4)
H13A	0.0127	0.7664	0.7464	0.067*
H13B	0.0203	0.7571	0.6579	0.067*
C14	0.2729 (2)	0.72520 (9)	0.71637 (10)	0.0455 (4)
C15	0.3311 (2)	0.67069 (9)	0.65689 (9)	0.0426 (3)
H15A	0.3234	0.6934	0.6071	0.051*
H15B	0.4642	0.6566	0.6685	0.051*
C16	0.20817 (19)	0.60537 (8)	0.65378 (8)	0.0368 (3)
C17	0.18772 (19)	0.48912 (8)	0.60097 (8)	0.0354 (3)
C18	0.2912 (2)	0.43901 (8)	0.55154 (9)	0.0406 (3)
H18A	0.4275	0.4393	0.5674	0.049*
H18B	0.2773	0.4558	0.4992	0.049*
C19	0.2145 (2)	0.36198 (9)	0.55528 (9)	0.0423 (3)
C20	−0.0053 (2)	0.36473 (9)	0.54550 (10)	0.0474 (4)
H20A	−0.0428	0.3803	0.4940	0.057*
H20B	−0.0557	0.3166	0.5517	0.057*
C21	−0.0958 (2)	0.41424 (9)	0.60100 (9)	0.0420 (3)
C22	0.01150 (19)	0.47845 (8)	0.62625 (8)	0.0367 (3)
C23	0.3742 (3)	0.79644 (10)	0.70260 (13)	0.0630 (5)
H23A	0.3381	0.8132	0.6520	0.094*
H23B	0.5113	0.7895	0.7080	0.094*
H23C	0.3369	0.8313	0.7392	0.094*
C24	0.3312 (3)	0.69813 (11)	0.79693 (10)	0.0565 (5)
H24A	0.4685	0.6916	0.8022	0.085*
H24B	0.2684	0.6531	0.8054	0.085*
H24C	0.2934	0.7327	0.8337	0.085*
C25	0.2778 (3)	0.32836 (10)	0.63219 (11)	0.0555 (4)
H25A	0.2259	0.2806	0.6348	0.083*
H25B	0.2313	0.3571	0.6726	0.083*
H25C	0.4161	0.3262	0.6375	0.083*
C26	0.2962 (3)	0.31780 (11)	0.49147 (12)	0.0645 (5)
H26A	0.2458	0.2698	0.4925	0.097*
H26B	0.4343	0.3163	0.4987	0.097*
H26C	0.2600	0.3396	0.4431	0.097*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.1401 (15)	0.1261 (13)	0.0658 (8)	0.0020 (11)	0.0231 (9)	0.0400 (8)
O1	0.0411 (6)	0.0750 (8)	0.0545 (7)	−0.0079 (6)	0.0193 (5)	0.0016 (6)
O2	0.0267 (5)	0.0454 (6)	0.0489 (6)	−0.0015 (4)	0.0099 (4)	−0.0043 (5)
O3	0.0291 (5)	0.0953 (10)	0.0562 (7)	0.0035 (6)	0.0084 (5)	0.0158 (7)
O4	0.0302 (6)	0.0743 (9)	0.0838 (9)	0.0068 (5)	0.0124 (6)	−0.0161 (7)
O5	0.0307 (6)	0.0703 (9)	0.0874 (10)	−0.0117 (5)	0.0089 (6)	−0.0105 (7)
C1	0.0328 (7)	0.0583 (10)	0.0502 (9)	−0.0036 (7)	0.0112 (6)	−0.0029 (7)
C2	0.0518 (9)	0.0494 (9)	0.0476 (9)	−0.0067 (7)	0.0141 (7)	−0.0031 (7)
C3	0.0758 (13)	0.0663 (13)	0.0569 (11)	−0.0111 (10)	0.0256 (10)	0.0029 (9)
C4	0.0988 (17)	0.0660 (13)	0.0505 (11)	−0.0014 (12)	0.0167 (11)	0.0118 (9)
C5	0.0844 (15)	0.0763 (15)	0.0595 (12)	0.0116 (12)	0.0021 (11)	0.0148 (10)
C6	0.0567 (11)	0.0704 (13)	0.0569 (11)	0.0086 (9)	0.0069 (8)	0.0093 (9)
C7	0.0450 (8)	0.0495 (9)	0.0449 (8)	−0.0012 (7)	0.0085 (7)	−0.0006 (7)
C8	0.0337 (7)	0.0547 (9)	0.0437 (8)	0.0001 (6)	0.0067 (6)	0.0002 (7)
C9	0.0281 (6)	0.0493 (9)	0.0441 (8)	−0.0018 (6)	0.0086 (6)	−0.0037 (7)
C10	0.0198 (6)	0.0507 (9)	0.0448 (8)	0.0012 (5)	0.0042 (5)	−0.0020 (6)
C11	0.0256 (6)	0.0478 (8)	0.0403 (7)	0.0026 (6)	0.0022 (5)	−0.0018 (6)
C12	0.0278 (7)	0.0563 (10)	0.0487 (9)	0.0072 (6)	−0.0007 (6)	−0.0057 (7)
C13	0.0418 (9)	0.0516 (10)	0.0745 (12)	0.0079 (7)	0.0023 (8)	−0.0099 (9)
C14	0.0379 (8)	0.0469 (9)	0.0517 (9)	−0.0029 (6)	0.0044 (6)	−0.0069 (7)
C15	0.0324 (7)	0.0503 (9)	0.0456 (8)	−0.0048 (6)	0.0070 (6)	−0.0011 (7)
C16	0.0278 (6)	0.0450 (8)	0.0377 (7)	0.0022 (6)	0.0028 (5)	−0.0009 (6)
C17	0.0280 (6)	0.0414 (8)	0.0367 (7)	0.0003 (5)	0.0019 (5)	0.0020 (6)
C18	0.0342 (7)	0.0466 (8)	0.0418 (8)	0.0029 (6)	0.0088 (6)	0.0014 (6)
C19	0.0376 (7)	0.0465 (9)	0.0430 (8)	0.0029 (6)	0.0054 (6)	0.0001 (7)
C20	0.0415 (8)	0.0520 (10)	0.0479 (9)	−0.0032 (7)	−0.0034 (7)	−0.0050 (7)
C21	0.0281 (7)	0.0509 (9)	0.0461 (8)	0.0004 (6)	−0.0031 (6)	0.0030 (7)
C22	0.0250 (6)	0.0462 (8)	0.0388 (7)	0.0018 (5)	0.0009 (5)	0.0010 (6)
C23	0.0614 (12)	0.0505 (11)	0.0772 (13)	−0.0082 (8)	0.0057 (10)	−0.0060 (9)
C24	0.0476 (10)	0.0734 (12)	0.0486 (9)	−0.0106 (8)	0.0038 (7)	−0.0075 (9)
C25	0.0487 (9)	0.0567 (11)	0.0611 (11)	0.0096 (8)	0.0034 (8)	0.0174 (9)
C26	0.0683 (12)	0.0607 (12)	0.0662 (12)	0.0054 (9)	0.0177 (10)	−0.0122 (9)

Geometric parameters (Å, º) top

F1—C4	1.349 (2)	C14—C23	1.527 (2)
O1—C1	1.359 (2)	C14—C15	1.528 (2)
O1—C2	1.363 (2)	C14—C24	1.532 (2)
O2—C17	1.3719 (18)	C15—C16	1.484 (2)
O2—C16	1.3744 (17)	C15—H15A	0.9700
O3—C8	1.2317 (18)	C15—H15B	0.9700
O4—C12	1.2192 (18)	C17—C22	1.3433 (18)
O5—C21	1.2243 (18)	C17—C18	1.489 (2)
C1—C9	1.3470 (19)	C18—C19	1.531 (2)
C1—H1A	0.9300	C18—H18A	0.9700
C2—C7	1.391 (2)	C18—H18B	0.9700
C2—C3	1.395 (3)	C19—C20	1.526 (2)
C3—C4	1.354 (3)	C19—C25	1.527 (2)
C3—H3A	0.9300	C19—C26	1.528 (2)
C4—C5	1.378 (3)	C20—C21	1.507 (2)
C5—C6	1.378 (3)	C20—H20A	0.9700
C5—H5A	0.9300	C20—H20B	0.9700
C6—C7	1.397 (3)	C21—C22	1.461 (2)
C6—H6A	0.9300	C23—H23A	0.9600
C7—C8	1.469 (2)	C23—H23B	0.9600
C8—C9	1.455 (2)	C23—H23C	0.9600
C9—C10	1.520 (2)	C24—H24A	0.9600
C10—C22	1.509 (2)	C24—H24B	0.9600
C10—C11	1.510 (2)	C24—H24C	0.9600
C10—H10A	0.9800	C25—H25A	0.9600
C11—C16	1.3402 (18)	C25—H25B	0.9600
C11—C12	1.471 (2)	C25—H25C	0.9600
C12—C13	1.503 (3)	C26—H26A	0.9600
C13—C14	1.534 (2)	C26—H26B	0.9600
C13—H13A	0.9700	C26—H26C	0.9600
C13—H13B	0.9700

C1—O1—C2	118.51 (12)	C14—C15—H15B	109.0
C17—O2—C16	117.92 (10)	H15A—C15—H15B	107.8
C9—C1—O1	125.01 (16)	C11—C16—O2	122.77 (14)
C9—C1—H1A	117.5	C11—C16—C15	125.73 (14)
O1—C1—H1A	117.5	O2—C16—C15	111.49 (11)
O1—C2—C7	121.73 (15)	C22—C17—O2	122.97 (13)
O1—C2—C3	116.91 (16)	C22—C17—C18	125.75 (14)
C7—C2—C3	121.36 (18)	O2—C17—C18	111.29 (11)
C4—C3—C2	117.71 (19)	C17—C18—C19	112.21 (12)
C4—C3—H3A	121.1	C17—C18—H18A	109.2
C2—C3—H3A	121.1	C19—C18—H18A	109.2
F1—C4—C3	118.7 (2)	C17—C18—H18B	109.2
F1—C4—C5	117.8 (2)	C19—C18—H18B	109.2
C3—C4—C5	123.53 (19)	H18A—C18—H18B	107.9
C6—C5—C4	118.2 (2)	C20—C19—C25	110.06 (13)
C6—C5—H5A	120.9	C20—C19—C26	110.59 (15)
C4—C5—H5A	120.9	C25—C19—C26	109.19 (15)
C5—C6—C7	121.02 (19)	C20—C19—C18	108.20 (13)
C5—C6—H6A	119.5	C25—C19—C18	109.84 (14)
C7—C6—H6A	119.5	C26—C19—C18	108.95 (13)
C2—C7—C6	118.21 (16)	C21—C20—C19	113.78 (13)
C2—C7—C8	120.19 (15)	C21—C20—H20A	108.8
C6—C7—C8	121.60 (15)	C19—C20—H20A	108.8
O3—C8—C9	123.44 (15)	C21—C20—H20B	108.8
O3—C8—C7	121.67 (15)	C19—C20—H20B	108.8
C9—C8—C7	114.89 (13)	H20A—C20—H20B	107.7
C1—C9—C8	119.57 (15)	O5—C21—C22	120.65 (14)
C1—C9—C10	119.69 (14)	O5—C21—C20	121.30 (15)
C8—C9—C10	120.73 (12)	C22—C21—C20	118.03 (13)
C22—C10—C11	108.70 (11)	C17—C22—C21	118.57 (13)
C22—C10—C9	111.76 (13)	C17—C22—C10	121.92 (13)
C11—C10—C9	111.17 (13)	C21—C22—C10	119.48 (12)
C22—C10—H10A	108.4	C14—C23—H23A	109.5
C11—C10—H10A	108.4	C14—C23—H23B	109.5
C9—C10—H10A	108.4	H23A—C23—H23B	109.5
C16—C11—C12	118.48 (14)	C14—C23—H23C	109.5
C16—C11—C10	122.12 (13)	H23A—C23—H23C	109.5
C12—C11—C10	119.40 (12)	H23B—C23—H23C	109.5
O4—C12—C11	120.52 (15)	C14—C24—H24A	109.5
O4—C12—C13	121.74 (15)	C14—C24—H24B	109.5
C11—C12—C13	117.66 (13)	H24A—C24—H24B	109.5
C12—C13—C14	113.74 (14)	C14—C24—H24C	109.5
C12—C13—H13A	108.8	H24A—C24—H24C	109.5
C14—C13—H13A	108.8	H24B—C24—H24C	109.5
C12—C13—H13B	108.8	C19—C25—H25A	109.5
C14—C13—H13B	108.8	C19—C25—H25B	109.5
H13A—C13—H13B	107.7	H25A—C25—H25B	109.5
C23—C14—C15	108.81 (14)	C19—C25—H25C	109.5
C23—C14—C24	109.51 (15)	H25A—C25—H25C	109.5
C15—C14—C24	110.32 (14)	H25B—C25—H25C	109.5
C23—C14—C13	110.57 (15)	C19—C26—H26A	109.5
C15—C14—C13	107.69 (13)	C19—C26—H26B	109.5
C24—C14—C13	109.92 (14)	H26A—C26—H26B	109.5
C16—C15—C14	113.03 (12)	C19—C26—H26C	109.5
C16—C15—H15A	109.0	H26A—C26—H26C	109.5
C14—C15—H15A	109.0	H26B—C26—H26C	109.5
C16—C15—H15B	109.0

C2—O1—C1—C9	−2.6 (3)	C11—C12—C13—C14	−33.4 (2)
C1—O1—C2—C7	2.8 (2)	C12—C13—C14—C23	173.48 (16)
C1—O1—C2—C3	−177.91 (16)	C12—C13—C14—C15	54.7 (2)
O1—C2—C3—C4	−179.30 (18)	C12—C13—C14—C24	−65.50 (19)
C7—C2—C3—C4	0.0 (3)	C23—C14—C15—C16	−166.89 (15)
C2—C3—C4—F1	179.54 (19)	C24—C14—C15—C16	72.95 (17)
C2—C3—C4—C5	0.2 (3)	C13—C14—C15—C16	−47.01 (19)
F1—C4—C5—C6	−180.0 (2)	C12—C11—C16—O2	−173.90 (13)
C3—C4—C5—C6	−0.7 (4)	C10—C11—C16—O2	6.7 (2)
C4—C5—C6—C7	0.9 (3)	C12—C11—C16—C15	5.1 (2)
O1—C2—C7—C6	179.51 (17)	C10—C11—C16—C15	−174.23 (14)
C3—C2—C7—C6	0.3 (3)	C17—O2—C16—C11	8.7 (2)
O1—C2—C7—C8	−0.4 (3)	C17—O2—C16—C15	−170.42 (12)
C3—C2—C7—C8	−179.60 (17)	C14—C15—C16—C11	19.2 (2)
C5—C6—C7—C2	−0.7 (3)	C14—C15—C16—O2	−161.68 (13)
C5—C6—C7—C8	179.15 (19)	C16—O2—C17—C22	−9.4 (2)
C2—C7—C8—O3	177.60 (17)	C16—O2—C17—C18	170.45 (12)
C6—C7—C8—O3	−2.2 (3)	C22—C17—C18—C19	−21.3 (2)
C2—C7—C8—C9	−2.3 (2)	O2—C17—C18—C19	158.87 (12)
C6—C7—C8—C9	177.86 (17)	C17—C18—C19—C20	47.87 (17)
O1—C1—C9—C8	−0.2 (3)	C17—C18—C19—C25	−72.29 (16)
O1—C1—C9—C10	−179.64 (15)	C17—C18—C19—C26	168.15 (14)
O3—C8—C9—C1	−177.33 (17)	C25—C19—C20—C21	65.87 (19)
C7—C8—C9—C1	2.6 (2)	C26—C19—C20—C21	−173.42 (15)
O3—C8—C9—C10	2.1 (3)	C18—C19—C20—C21	−54.16 (18)
C7—C8—C9—C10	−178.01 (14)	C19—C20—C21—O5	−149.34 (16)
C1—C9—C10—C22	−121.20 (15)	C19—C20—C21—C22	32.2 (2)
C8—C9—C10—C22	59.36 (18)	O2—C17—C22—C21	176.60 (13)
C1—C9—C10—C11	117.14 (16)	C18—C17—C22—C21	−3.2 (2)
C8—C9—C10—C11	−62.29 (18)	O2—C17—C22—C10	−5.4 (2)
C22—C10—C11—C16	−18.99 (19)	C18—C17—C22—C10	174.73 (14)
C9—C10—C11—C16	104.44 (16)	O5—C21—C22—C17	179.38 (15)
C22—C10—C11—C12	161.65 (13)	C20—C21—C22—C17	−2.2 (2)
C9—C10—C11—C12	−74.93 (16)	O5—C21—C22—C10	1.4 (2)
C16—C11—C12—O4	179.18 (16)	C20—C21—C22—C10	179.80 (13)
C10—C11—C12—O4	−1.4 (2)	C11—C10—C22—C17	18.33 (19)
C16—C11—C12—C13	2.2 (2)	C9—C10—C22—C17	−104.74 (16)
C10—C11—C12—C13	−178.44 (15)	C11—C10—C22—C21	−163.73 (13)
O4—C12—C13—C14	149.58 (17)	C9—C10—C22—C21	73.20 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···O4ⁱ	0.97	2.44	3.3487 (19)	156
C18—H18A···O5ⁱ	0.97	2.45	3.3821 (19)	162

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₅FO₅
M_r	436.46
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	6.9475 (8), 18.596 (2), 17.559 (2)
β (°)	93.658 (2)
V (Å³)	2264.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.51 × 0.38 × 0.24

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.954, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	21143, 6574, 4315
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.150, 1.03
No. of reflections	6574
No. of parameters	293
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.22

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···O4ⁱ	0.97	2.44	3.3487 (19)	156
C18—H18A···O5ⁱ	0.97	2.45	3.3821 (19)	162

Symmetry code: (i) x+1, y, z.

Footnotes

‡Additional correspondence author, e-mail: oocw@usm.my.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grants (1001/PFIZIK/811160) and (203/PKIMIA/6711179). SA thanks the Malaysian Government and USM for the Academic Staff Training Scheme (ASTS) award. MA also thanks Universiti Sains Malaysia for the award of a post-doctoral fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Mehdi, S. H., Sulaiman, O., Ghalib, R. M., Yeap, C. S. & Fun, H.-K. (2011). Acta Cryst. E67, o1719–o1720. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

9-(7-Fluoro-4-oxo-4H-chromen-3-yl)-3,3,6,6-tetra­methyl-2,3,4,5,6,7,8,9-octa­hydro-1H-xanthene-1,8-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

9-(7-Fluoro-4-oxo-4H-chromen-3-yl)-3,3,6,6-tetramethyl-2,3,4,5,6,7,8,9-octahydro-1H-xanthene-1,8-dione