9-(4-Fluoro­phen­yl)-3,3,6,6-tetra­methyl-10-p-tolyl-1,2,3,4,5,6,7,8,9,10-deca­hydroacridine-1,8-dione

Tang, Z.; Liu, C.; Wu, S.; Hao, W.

doi:10.1107/S1600536808027256

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1844

doi:10.1107/S1600536808027256

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9-(4-Fluorophenyl)-3,3,6,6-tetramethyl-10-p-tolyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione

Ziqiang Tang,^a ^* Changning Liu,^a Shanshan Wu ^b and Wenjuan Hao ^b

^aSchool of Chemistry and Chemical Engineering, Xuzhou Institute of Technology, Xuzhou 221006, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, People's Republic of China
^*Correspondence e-mail: laotu2001@263.net

(Received 20 August 2008; accepted 24 August 2008; online 30 August 2008)

The title compound, C₃₀H₃₂FNO₂, was synthesized by the reaction of dimedone with 4-fluorobenzaldehyde and p-toluidine in water. The dihydropyridine and both of the cyclohexenone rings are not planar and have flattened boat conformations. The dihedral angle between the planar aromatic rings is 15.33 (3)°. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For general background, see: Wysocka-Skrzela & Ledochowski (1976 ); Nasim & Brychcy (1979 ); Thull & Testa, (1994 ); Reil et al. (1994 ); Mandi et al. (1994 ). For related literature, see: Tu et al. (2004 ). For ring puckering parameters, see: Cremer & Pople (1975 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₃₀H₃₂FNO₂
M_r = 457.58
Monoclinic, P 2₁ /n
a = 15.1533 (15) Å
b = 10.9643 (12) Å
c = 16.1053 (15) Å
β = 102.317 (2)°
V = 2614.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.37 × 0.25 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.972, T_max = 0.984
13238 measured reflections
4605 independent reflections
2277 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.152
S = 1.02
4605 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O1ⁱ	0.93	2.45	3.336 (3)	159
Symmetry code: (i) -x+2, -y+1, -z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027256/hk2514sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027256/hk2514Isup2.hkl

checkCIF report

Comment top

Acridine derivatives containing 1,4-dihydropyridine unit belong to a special class of compounds not only because of their interesting chemical and physical properties but also due to their immense utility in pharmaceutical and dye industry, and they are well known atherapeutic agents (Wysocka-Skrzela & Ledochowski, 1976; Nasim & Brychcy, 1979; Thull & Testa, 1994; Reil et al., 1994; Mandi et al., 1994). We have reported the synthesis of N-hydroxylacridine derivatives, previously, (Tu et al., 2004) and we report herein the structure of the title compound.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are generally within normal ranges. Rings D (C14-C19) and E (C21-C26) are, of course, planar and they are oriented at a dihedral angle of D/E = 15.33 (3)°. Rings A (C1-C6), B (N1/C1/C6-C8/C13) and C (C8-C13) are not planar, having total puckering amplitudes, Q_T, of 0.475 (3), 0.201 (2) and 0.448 (3) Å, respectively, and flattened boat conformations [ϕ = -56.70 (3)°, θ = 120.78 (3)°; ϕ = 172.92 (2)°, θ = 76.41 (3)° and ϕ = 170.16 (3)°, θ = 54.52 (3)°, respectively] (Cremer & Pople, 1975).

In the crystal structure, intermolecular C-H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For general background, see: Wysocka-Skrzela & Ledochowski (1976); Nasim & Brychcy (1979); Thull & Testa, (1994); Reil et al. (1994); Mandi et al. (1994). For related literature, see: Tu et al. (2004). For ring puckering parameters, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by the reaction of dimedone (2 mmol) with 4-fluorobenzaldehyde (1 mmol) and p-toluidine in water (1 mmol) at 413 K under microwave irradiation (maximum power 140 W, initial power 120 W) for 12 min (yield; 89%). Single crystals suitable for X-ray analysis were obtained from an ethanol solution by slow evaporation.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

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 the title compound. Hydrogen bonds are shown as dashed lines.

9-(4-Fluorophenyl)-3,3,6,6-tetramethyl-10-p-tolyl-1,2,3,4,5,6,7,8,9,10- decahydroacridine-1,8-dione top

Crystal data top

C₃₀H₃₂FNO₂	F(000) = 976
M_r = 457.58	D_x = 1.163 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 540–541 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 15.1533 (15) Å	Cell parameters from 2294 reflections
b = 10.9643 (12) Å	θ = 2.3–2.3°
c = 16.1053 (15) Å	µ = 0.08 mm⁻¹
β = 102.317 (2)°	T = 298 K
V = 2614.2 (5) Å³	Block, pale yellow
Z = 4	0.37 × 0.25 × 0.21 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4605 independent reflections
Radiation source: fine-focus sealed tube	2277 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→18
T_min = 0.972, T_max = 0.984	k = −13→12
13238 measured reflections	l = −13→19

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) = 0.152	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0429P)² + 1.7217P] where P = (F_o² + 2F_c²)/3
4605 reflections	(Δ/σ)_max < 0.001
307 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₃₀H₃₂FNO₂	V = 2614.2 (5) Å³
M_r = 457.58	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.1533 (15) Å	µ = 0.08 mm⁻¹
b = 10.9643 (12) Å	T = 298 K
c = 16.1053 (15) Å	0.37 × 0.25 × 0.21 mm
β = 102.317 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4605 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2277 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.984	R_int = 0.045
13238 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.02	Δρ_max = 0.18 e Å⁻³
4605 reflections	Δρ_min = −0.21 e Å⁻³
307 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	0.73692 (17)	−0.0186 (2)	0.21288 (18)	0.1213 (10)
N1	0.99513 (16)	0.5507 (2)	0.20652 (15)	0.0415 (6)
O1	0.89407 (16)	0.3144 (2)	−0.03980 (14)	0.0634 (7)
O2	1.13495 (16)	0.1657 (2)	0.20291 (16)	0.0695 (7)
C1	0.93912 (19)	0.5309 (2)	0.12692 (19)	0.0389 (7)
C2	0.8806 (2)	0.6360 (3)	0.08813 (19)	0.0485 (8)
H2A	0.9169	0.6920	0.0628	0.058*
H2B	0.8599	0.6794	0.1329	0.058*
C3	0.7985 (2)	0.5977 (3)	0.0204 (2)	0.0507 (8)
C4	0.8317 (2)	0.5133 (3)	−0.0417 (2)	0.0545 (9)
H4A	0.7797	0.4807	−0.0814	0.065*
H4B	0.8668	0.5606	−0.0740	0.065*
C5	0.8883 (2)	0.4090 (3)	0.00008 (19)	0.0442 (8)
C6	0.93853 (19)	0.4227 (2)	0.08715 (18)	0.0372 (7)
C7	0.98875 (19)	0.3129 (2)	0.12966 (18)	0.0393 (7)
H7	1.0187	0.2735	0.0885	0.047*
C8	1.06046 (19)	0.3524 (2)	0.20419 (19)	0.0398 (7)
C9	1.1334 (2)	0.2666 (3)	0.2352 (2)	0.0504 (8)
C10	1.2098 (2)	0.3074 (3)	0.3049 (2)	0.0711 (11)
H10A	1.2559	0.3447	0.2797	0.085*
H10B	1.2364	0.2364	0.3366	0.085*
C11	1.1820 (3)	0.3972 (3)	0.3660 (2)	0.0678 (11)
C12	1.1319 (2)	0.5027 (3)	0.3152 (2)	0.0572 (9)
H12A	1.1037	0.5516	0.3525	0.069*
H12B	1.1753	0.5540	0.2954	0.069*
C13	1.06083 (19)	0.4636 (2)	0.24020 (18)	0.0405 (7)
C14	0.9980 (2)	0.6695 (2)	0.24664 (19)	0.0405 (7)
C15	1.0480 (2)	0.7618 (3)	0.2215 (2)	0.0456 (8)
H15	1.0790	0.7485	0.1783	0.055*
C16	1.0518 (2)	0.8741 (3)	0.2606 (2)	0.0485 (8)
H16	1.0857	0.9363	0.2435	0.058*
C17	1.0058 (2)	0.8960 (3)	0.3249 (2)	0.0498 (8)
C18	0.9566 (2)	0.8024 (3)	0.3491 (2)	0.0584 (9)
H18	0.9258	0.8153	0.3925	0.070*
C19	0.9519 (2)	0.6893 (3)	0.3101 (2)	0.0530 (9)
H19	0.9177	0.6271	0.3268	0.064*
C20	1.0093 (3)	1.0207 (3)	0.3652 (2)	0.0731 (11)
H20A	0.9604	1.0696	0.3347	0.110*
H20B	1.0657	1.0591	0.3633	0.110*
H20C	1.0038	1.0126	0.4232	0.110*
C21	0.9223 (2)	0.2213 (2)	0.15367 (18)	0.0410 (7)
C22	0.9213 (2)	0.1009 (3)	0.1283 (2)	0.0535 (9)
H22	0.9627	0.0739	0.0973	0.064*
C23	0.8588 (3)	0.0196 (3)	0.1489 (2)	0.0692 (11)
H23	0.8580	−0.0616	0.1321	0.083*
C24	0.7990 (3)	0.0615 (4)	0.1941 (3)	0.0720 (11)
C25	0.7985 (3)	0.1776 (4)	0.2209 (3)	0.0757 (12)
H25	0.7572	0.2030	0.2525	0.091*
C26	0.8606 (2)	0.2581 (3)	0.2007 (2)	0.0563 (9)
H26	0.8609	0.3386	0.2191	0.068*
C27	0.7548 (3)	0.7116 (3)	−0.0263 (2)	0.0761 (12)
H27A	0.7360	0.7657	0.0135	0.114*
H27B	0.7033	0.6881	−0.0691	0.114*
H27C	0.7978	0.7524	−0.0526	0.114*
C28	0.7295 (2)	0.5314 (3)	0.0606 (2)	0.0696 (11)
H28A	0.7564	0.4592	0.0889	0.104*
H28B	0.6781	0.5093	0.0172	0.104*
H28C	0.7105	0.5842	0.1011	0.104*
C29	1.2664 (3)	0.4479 (3)	0.4266 (3)	0.1137 (19)
H29A	1.2483	0.4989	0.4684	0.171*
H29B	1.3013	0.4948	0.3948	0.171*
H29C	1.3022	0.3815	0.4544	0.171*
C30	1.1203 (4)	0.3354 (4)	0.4167 (3)	0.1026 (16)
H30A	1.0663	0.3081	0.3787	0.154*
H30B	1.1048	0.3925	0.4565	0.154*
H30C	1.1510	0.2668	0.4469	0.154*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0961 (19)	0.1090 (19)	0.155 (2)	−0.0497 (16)	0.0192 (17)	0.0503 (18)
N1	0.0426 (15)	0.0312 (13)	0.0459 (16)	0.0000 (11)	−0.0012 (12)	−0.0048 (11)
O1	0.0785 (18)	0.0585 (15)	0.0505 (15)	−0.0079 (13)	0.0076 (12)	−0.0145 (12)
O2	0.0646 (17)	0.0463 (14)	0.0919 (19)	0.0124 (12)	0.0039 (14)	−0.0141 (13)
C1	0.0361 (17)	0.0409 (17)	0.0382 (19)	−0.0049 (14)	0.0043 (14)	0.0037 (14)
C2	0.049 (2)	0.0423 (17)	0.051 (2)	0.0021 (15)	0.0023 (16)	−0.0008 (15)
C3	0.046 (2)	0.053 (2)	0.050 (2)	−0.0016 (17)	0.0020 (16)	0.0043 (16)
C4	0.057 (2)	0.062 (2)	0.041 (2)	−0.0095 (18)	0.0010 (16)	0.0063 (17)
C5	0.046 (2)	0.0477 (19)	0.0393 (19)	−0.0125 (16)	0.0105 (15)	−0.0029 (16)
C6	0.0376 (17)	0.0364 (16)	0.0368 (18)	−0.0066 (14)	0.0062 (14)	−0.0008 (13)
C7	0.0415 (18)	0.0359 (16)	0.0404 (18)	−0.0031 (14)	0.0087 (14)	−0.0067 (14)
C8	0.0363 (18)	0.0353 (16)	0.047 (2)	−0.0025 (14)	0.0062 (15)	−0.0010 (14)
C9	0.046 (2)	0.0369 (18)	0.065 (2)	−0.0009 (15)	0.0051 (17)	−0.0025 (16)
C10	0.061 (2)	0.050 (2)	0.089 (3)	0.0101 (19)	−0.015 (2)	−0.001 (2)
C11	0.081 (3)	0.046 (2)	0.062 (2)	0.004 (2)	−0.018 (2)	0.0009 (19)
C12	0.060 (2)	0.0403 (18)	0.061 (2)	−0.0004 (16)	−0.0105 (18)	−0.0054 (16)
C13	0.0396 (18)	0.0340 (16)	0.044 (2)	−0.0022 (14)	0.0012 (15)	−0.0003 (14)
C14	0.0408 (19)	0.0330 (16)	0.044 (2)	0.0009 (14)	0.0016 (15)	−0.0054 (14)
C15	0.0439 (19)	0.0419 (18)	0.050 (2)	−0.0034 (15)	0.0084 (15)	−0.0062 (15)
C16	0.049 (2)	0.0406 (18)	0.054 (2)	−0.0056 (15)	0.0059 (17)	0.0000 (15)
C17	0.052 (2)	0.0434 (19)	0.048 (2)	0.0073 (16)	−0.0028 (17)	−0.0074 (16)
C18	0.064 (2)	0.058 (2)	0.056 (2)	0.0031 (19)	0.0190 (18)	−0.0095 (18)
C19	0.057 (2)	0.0455 (19)	0.058 (2)	−0.0042 (17)	0.0164 (18)	−0.0023 (16)
C20	0.086 (3)	0.053 (2)	0.072 (3)	0.011 (2)	−0.001 (2)	−0.0208 (19)
C21	0.0423 (19)	0.0354 (16)	0.0423 (19)	−0.0061 (14)	0.0023 (15)	−0.0013 (14)
C22	0.061 (2)	0.0388 (18)	0.056 (2)	−0.0052 (17)	0.0011 (17)	−0.0027 (16)
C23	0.079 (3)	0.040 (2)	0.074 (3)	−0.018 (2)	−0.016 (2)	0.0088 (18)
C24	0.056 (3)	0.068 (3)	0.087 (3)	−0.020 (2)	0.004 (2)	0.030 (2)
C25	0.065 (3)	0.074 (3)	0.094 (3)	−0.002 (2)	0.030 (2)	0.022 (2)
C26	0.059 (2)	0.050 (2)	0.065 (2)	−0.0017 (17)	0.0231 (19)	0.0075 (17)
C27	0.070 (3)	0.070 (2)	0.076 (3)	0.012 (2)	−0.012 (2)	0.011 (2)
C28	0.047 (2)	0.091 (3)	0.069 (3)	−0.006 (2)	0.0102 (19)	0.002 (2)
C29	0.120 (4)	0.060 (3)	0.116 (4)	0.016 (3)	−0.074 (3)	−0.015 (3)
C30	0.169 (5)	0.073 (3)	0.060 (3)	−0.002 (3)	0.011 (3)	0.004 (2)

Geometric parameters (Å, º) top

F1—C24	1.367 (4)	C14—C15	1.376 (4)
N1—C1	1.395 (4)	C15—C16	1.379 (4)
N1—C13	1.403 (3)	C15—H15	0.9300
N1—C14	1.450 (3)	C16—C17	1.386 (4)
O1—C5	1.233 (3)	C16—H16	0.9300
O2—C9	1.225 (3)	C17—C18	1.373 (4)
C1—C6	1.347 (4)	C17—C20	1.510 (4)
C1—C2	1.506 (4)	C18—C19	1.386 (4)
C2—C3	1.528 (4)	C18—H18	0.9300
C2—H2A	0.9700	C19—H19	0.9300
C2—H2B	0.9700	C20—H20A	0.9600
C3—C4	1.524 (4)	C20—H20B	0.9600
C3—C28	1.527 (4)	C20—H20C	0.9600
C3—C27	1.534 (4)	C21—C22	1.381 (4)
C4—C5	1.499 (4)	C21—C26	1.384 (4)
C4—H4A	0.9700	C22—C23	1.391 (4)
C4—H4B	0.9700	C22—H22	0.9300
C5—C6	1.454 (4)	C23—C24	1.358 (5)
C6—C7	1.509 (4)	C23—H23	0.9300
C7—C8	1.501 (4)	C24—C25	1.344 (5)
C7—C21	1.528 (4)	C25—C26	1.378 (4)
C7—H7	0.9800	C25—H25	0.9300
C8—C13	1.349 (4)	C26—H26	0.9300
C8—C9	1.457 (4)	C27—H27A	0.9600
C9—C10	1.498 (4)	C27—H27B	0.9600
C10—C11	1.514 (5)	C27—H27C	0.9600
C10—H10A	0.9700	C28—H28A	0.9600
C10—H10B	0.9700	C28—H28B	0.9600
C11—C12	1.523 (4)	C28—H28C	0.9600
C11—C30	1.525 (5)	C29—H29A	0.9600
C11—C29	1.538 (5)	C29—H29B	0.9600
C12—C13	1.499 (4)	C29—H29C	0.9600
C12—H12A	0.9700	C30—H30A	0.9600
C12—H12B	0.9700	C30—H30B	0.9600
C14—C19	1.373 (4)	C30—H30C	0.9600

C1—N1—C13	119.5 (2)	C15—C14—N1	119.7 (3)
C1—N1—C14	120.3 (2)	C14—C15—C16	119.6 (3)
C13—N1—C14	119.2 (2)	C14—C15—H15	120.2
C6—C1—N1	121.0 (3)	C16—C15—H15	120.2
C6—C1—C2	122.2 (3)	C15—C16—C17	121.1 (3)
N1—C1—C2	116.8 (2)	C15—C16—H16	119.4
C1—C2—C3	113.8 (2)	C17—C16—H16	119.4
C1—C2—H2A	108.8	C18—C17—C16	118.2 (3)
C3—C2—H2A	108.8	C18—C17—C20	121.7 (3)
C1—C2—H2B	108.8	C16—C17—C20	120.1 (3)
C3—C2—H2B	108.8	C17—C18—C19	121.2 (3)
H2A—C2—H2B	107.7	C17—C18—H18	119.4
C4—C3—C28	109.9 (3)	C19—C18—H18	119.4
C4—C3—C2	107.7 (3)	C14—C19—C18	119.6 (3)
C28—C3—C2	110.8 (3)	C14—C19—H19	120.2
C4—C3—C27	109.9 (3)	C18—C19—H19	120.2
C28—C3—C27	109.4 (3)	C17—C20—H20A	109.5
C2—C3—C27	109.1 (3)	C17—C20—H20B	109.5
C5—C4—C3	114.0 (3)	H20A—C20—H20B	109.5
C5—C4—H4A	108.8	C17—C20—H20C	109.5
C3—C4—H4A	108.8	H20A—C20—H20C	109.5
C5—C4—H4B	108.8	H20B—C20—H20C	109.5
C3—C4—H4B	108.8	C22—C21—C26	118.3 (3)
H4A—C4—H4B	107.7	C22—C21—C7	121.3 (3)
O1—C5—C6	120.6 (3)	C26—C21—C7	120.4 (3)
O1—C5—C4	120.4 (3)	C21—C22—C23	120.5 (3)
C6—C5—C4	119.0 (3)	C21—C22—H22	119.7
C1—C6—C5	119.9 (3)	C23—C22—H22	119.7
C1—C6—C7	122.4 (3)	C24—C23—C22	118.5 (3)
C5—C6—C7	117.7 (2)	C24—C23—H23	120.8
C8—C7—C6	109.9 (2)	C22—C23—H23	120.8
C8—C7—C21	113.0 (2)	C25—C24—C23	122.8 (3)
C6—C7—C21	110.1 (2)	C25—C24—F1	119.1 (4)
C8—C7—H7	107.9	C23—C24—F1	118.1 (4)
C6—C7—H7	107.9	C24—C25—C26	118.7 (4)
C21—C7—H7	107.9	C24—C25—H25	120.6
C13—C8—C9	120.2 (3)	C26—C25—H25	120.6
C13—C8—C7	122.7 (3)	C25—C26—C21	121.2 (3)
C9—C8—C7	117.0 (2)	C25—C26—H26	119.4
O2—C9—C8	121.3 (3)	C21—C26—H26	119.4
O2—C9—C10	120.4 (3)	C3—C27—H27A	109.5
C8—C9—C10	118.2 (3)	C3—C27—H27B	109.5
C9—C10—C11	113.7 (3)	H27A—C27—H27B	109.5
C9—C10—H10A	108.8	C3—C27—H27C	109.5
C11—C10—H10A	108.8	H27A—C27—H27C	109.5
C9—C10—H10B	108.8	H27B—C27—H27C	109.5
C11—C10—H10B	108.8	C3—C28—H28A	109.5
H10A—C10—H10B	107.7	C3—C28—H28B	109.5
C10—C11—C12	108.8 (3)	H28A—C28—H28B	109.5
C10—C11—C30	110.3 (3)	C3—C28—H28C	109.5
C12—C11—C30	109.5 (3)	H28A—C28—H28C	109.5
C10—C11—C29	109.7 (3)	H28B—C28—H28C	109.5
C12—C11—C29	108.6 (3)	C11—C29—H29A	109.5
C30—C11—C29	110.0 (4)	C11—C29—H29B	109.5
C13—C12—C11	113.9 (3)	H29A—C29—H29B	109.5
C13—C12—H12A	108.8	C11—C29—H29C	109.5
C11—C12—H12A	108.8	H29A—C29—H29C	109.5
C13—C12—H12B	108.8	H29B—C29—H29C	109.5
C11—C12—H12B	108.8	C11—C30—H30A	109.5
H12A—C12—H12B	107.7	C11—C30—H30B	109.5
C8—C13—N1	120.7 (3)	H30A—C30—H30B	109.5
C8—C13—C12	122.8 (3)	C11—C30—H30C	109.5
N1—C13—C12	116.4 (2)	H30A—C30—H30C	109.5
C19—C14—C15	120.2 (3)	H30B—C30—H30C	109.5
C19—C14—N1	120.1 (3)

C13—N1—C1—C6	9.2 (4)	C30—C11—C12—C13	−73.3 (4)
C14—N1—C1—C6	177.1 (3)	C29—C11—C12—C13	166.6 (3)
C13—N1—C1—C2	−170.4 (3)	C9—C8—C13—N1	174.7 (3)
C14—N1—C1—C2	−2.5 (4)	C7—C8—C13—N1	−2.9 (4)
C6—C1—C2—C3	21.9 (4)	C9—C8—C13—C12	−3.1 (5)
N1—C1—C2—C3	−158.5 (3)	C7—C8—C13—C12	179.4 (3)
C1—C2—C3—C4	−49.8 (3)	C1—N1—C13—C8	−11.6 (4)
C1—C2—C3—C28	70.4 (4)	C14—N1—C13—C8	−179.6 (3)
C1—C2—C3—C27	−169.1 (3)	C1—N1—C13—C12	166.3 (3)
C28—C3—C4—C5	−68.6 (3)	C14—N1—C13—C12	−1.7 (4)
C2—C3—C4—C5	52.1 (3)	C11—C12—C13—C8	−20.7 (5)
C27—C3—C4—C5	170.8 (3)	C11—C12—C13—N1	161.5 (3)
C3—C4—C5—O1	155.5 (3)	C1—N1—C14—C19	101.5 (3)
C3—C4—C5—C6	−26.6 (4)	C13—N1—C14—C19	−90.5 (3)
N1—C1—C6—C5	−172.3 (2)	C1—N1—C14—C15	−79.2 (4)
C2—C1—C6—C5	7.2 (4)	C13—N1—C14—C15	88.8 (3)
N1—C1—C6—C7	7.6 (4)	C19—C14—C15—C16	0.3 (5)
C2—C1—C6—C7	−172.8 (3)	N1—C14—C15—C16	−179.0 (3)
O1—C5—C6—C1	173.0 (3)	C14—C15—C16—C17	−0.2 (5)
C4—C5—C6—C1	−4.9 (4)	C15—C16—C17—C18	0.3 (5)
O1—C5—C6—C7	−6.9 (4)	C15—C16—C17—C20	−178.5 (3)
C4—C5—C6—C7	175.2 (3)	C16—C17—C18—C19	−0.6 (5)
C1—C6—C7—C8	−19.6 (4)	C20—C17—C18—C19	178.3 (3)
C5—C6—C7—C8	160.3 (2)	C15—C14—C19—C18	−0.5 (5)
C1—C6—C7—C21	105.5 (3)	N1—C14—C19—C18	178.8 (3)
C5—C6—C7—C21	−74.6 (3)	C17—C18—C19—C14	0.7 (5)
C6—C7—C8—C13	17.3 (4)	C8—C7—C21—C22	−110.1 (3)
C21—C7—C8—C13	−106.2 (3)	C6—C7—C21—C22	126.5 (3)
C6—C7—C8—C9	−160.4 (2)	C8—C7—C21—C26	70.8 (4)
C21—C7—C8—C9	76.2 (3)	C6—C7—C21—C26	−52.6 (4)
C13—C8—C9—O2	−179.3 (3)	C26—C21—C22—C23	0.8 (5)
C7—C8—C9—O2	−1.5 (4)	C7—C21—C22—C23	−178.3 (3)
C13—C8—C9—C10	−2.6 (5)	C21—C22—C23—C24	0.2 (5)
C7—C8—C9—C10	175.1 (3)	C22—C23—C24—C25	−1.1 (6)
O2—C9—C10—C11	−151.3 (3)	C22—C23—C24—F1	179.0 (3)
C8—C9—C10—C11	32.0 (4)	C23—C24—C25—C26	1.0 (6)
C9—C10—C11—C12	−53.0 (4)	F1—C24—C25—C26	−179.2 (3)
C9—C10—C11—C30	67.1 (4)	C24—C25—C26—C21	0.1 (6)
C9—C10—C11—C29	−171.6 (3)	C22—C21—C26—C25	−1.0 (5)
C10—C11—C12—C13	47.2 (4)	C7—C21—C26—C25	178.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1ⁱ	0.93	2.45	3.336 (3)	159

Symmetry code: (i) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₃₀H₃₂FNO₂
M_r	457.58
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	15.1533 (15), 10.9643 (12), 16.1053 (15)
β (°)	102.317 (2)
V (Å³)	2614.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.37 × 0.25 × 0.21

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.972, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	13238, 4605, 2277
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.152, 1.02
No. of reflections	4605
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.21

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1ⁱ	0.93	2.45	3.336 (3)	159.00

Symmetry code: (i) −x+2, −y+1, −z.

Acknowledgements

We thank the Foundation of Xuzhou Institute of Technology (grant No. XKY2007241) for financial support.

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 (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Mandi, Y., Regely, K., Ocsovszky, I., Barbe, J., Galy, J. P. & Molnar, J. (1994). Anticancer Res. 14, 2633–2636. CAS PubMed Web of Science Google Scholar
Nasim, A. & Brychcy, T. (1979). Mutat. Res. 65, 261–288. CrossRef CAS PubMed Web of Science Google Scholar
Reil, E., Scoll, M., Masson, K. & Oettmeier, W. (1994). Biochem. Soc. Trans. 22, s62. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thull, U. & Testa, B. (1994). Biochem. Pharmacol. 47, 2307–2310. CrossRef CAS PubMed Web of Science Google Scholar
Tu, S. J., Miao, C. B., Gao, Y., Fang, F., Zhuang, Q. Y., Feng, Y. J. & Shi, D. Q. (2004). Synlett, 2, 255–258. Web of Science CSD CrossRef Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

9-(4-Fluoro­phen­yl)-3,3,6,6-tetra­methyl-10-p-tolyl-1,2,3,4,5,6,7,8,9,10-deca­hydroacridine-1,8-dione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

9-(4-Fluorophenyl)-3,3,6,6-tetramethyl-10-p-tolyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione