10-(4-Chloro­phen­yl)-9-(4-fluoro­phen­yl)-3,3,6,6-tetra­methyl-3,4,6,7,9,10-hexa­hydro­acridine-1,8(2H,5H)-dione

Zhao, L.-L.; Teng, D.

doi:10.1107/S1600536808025695

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 9| September 2008| Pages o1772-o1773

doi:10.1107/S1600536808025695

Open

access

10-(4-Chlorophenyl)-9-(4-fluorophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione

Ling-Ling Zhao ^a ^* and Da Teng ^a

^aSchool of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, People's Republic of China
^*Correspondence e-mail: zllcpu@163.com

(Received 25 June 2008; accepted 9 August 2008; online 16 August 2008)

The title compound, C₂₉H₂₉ClFNO₂, was synthesized by the reaction of 4-fluorobenzaldehyde, 5,5-dimethylcyclohexane-1,3-dione and 3-(4-chlorophenylamino)-5,5-dimethylcyclohex-2-enone in an ionic liquid (1-butyl-3-methylimidazolium bromide). X-ray analysis reveals that the 1,4-dihydropyridine ring adopts a boat conformation, while each of the attached partially saturated six-membered rings adopts a half-chair conformation. The structure is stabilized by weak C—H⋯O and C—H⋯F hydrogen bonds. The molecule has approximate mirror symmetry; the largest deviation from this symmetry concerns the fluoro- and chlorophenyl rings.

Related literature

For related literature, see: Dzierzbicka et al. (2001 ); Hutchins et al. (2003 ); Kamal et al. (2004 ); Li et al. (2003 ); Petříček et al. (2000 ); Srivastava & Nizamuddin (2004 ); Wang et al. (2002 , 2003 ).

Experimental

Crystal data

C₂₉H₂₉ClFNO₂
M_r = 477.98
Monoclinic, P 2₁ /c
a = 12.0985 (12) Å
b = 10.9001 (10) Å
c = 19.4724 (18) Å
β = 101.231 (3)°
V = 2518.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 113 (2) K
0.32 × 0.20 × 0.18 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 1999 ) T_min = 0.943, T_max = 0.967
30908 measured reflections
6016 independent reflections
5436 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.137
S = 1.10
6016 reflections
312 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16C⋯O2ⁱ	0.98	2.45	3.359 (2)	153
C11—H11⋯O2ⁱⁱ	0.95	2.37	3.286 (2)	160
C10—H10⋯O1ⁱⁱⁱ	0.95	2.55	3.474 (2)	165
C16—H16A⋯O1^iv	0.98	2.59	3.528 (2)	159
C17—H17A⋯F1^v	0.98	2.45	3.373 (2)	157
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z; (iii) x, y+1, z; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025695/fb2102sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025695/fb2102Isup2.hkl

checkCIF report

Comment top

Acridine derivatives are well-known compounds because of their pharmacological profile as anticancer agents (Hutchins et al., 2003) and potential DNA-binding agents (Kamal et al., 2004). Acridine derivatives have also been reported to possess antitumor activity (Dzierzbicka et al., 2001) as well as fungicidal activity (Srivastava & Nizamuddin, 2004). Here we report the crystal structure of 10-(4-chlorophenyl)-9-(4-fluorophenyl)-3,4,6,7-tetrahydro-3,3,6,6- tetramethylacridine-1,8(2H,5H,9H,10H)-dione.

The X-ray crystal structure determination indicates that the central 1,4-dihydropyridine ring C1/C2···N1 is slightly distorted and adopts the boat conformation. The atoms C1, C2, C4 and C5 are coplanar, with C3 and N1 deviating from the plane by 0.286 (3) and 0.109 (2) Å, respectively. The similar distortions have been observed in the structures of 3,3,6,6-tetramethyl-9-(4-chlorophenyl)-10-(4-methylphenyl)- 1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione [0.192 (3) and 0.091 (3) Å for C13 and N, respectively; Wang et al., 2003) and 3,3,6,6-tetramethyl-9-(3,4-methylenedioxylphenyl)-1,2,3,4,5,6,7,8,9,10- decahydroacridine-1,8-dione [0.313 (7) and 0.107 (7) Å for C7 and N1, respectively; Li et al., 2003).

The two outer six-membered rings of the acridine group adopt half-chair conformations; the atoms C13 and C19 deviate from the mean planes defined by C1, C2, C14, C15, C12 and C4, C5, C18, C20, C21 by 0.657 (2) and 0.668 (2) Å, respectively. A similar conformation has been found in the structure of 7,7-dimethyl-2-amino-3-cyano-4-(3,4-methylenedioxylphenyl)-5-oxo-5,6,7,8- tetrahydro-4H-benzo-[b]-pyran (Wang et al., 2002).

The 4-fluorophenyl ring is nearly perpendicular to the plane defined by the atoms C1—C2—C4—C5, forming a dihedral angle of 87.9 (1)°. The molecule has an approximate mirror symmetry. For example, the atoms C14 and C20 of the acridine groups are deviated by about 0.25Å. (The calculation has been carried out with the help of JANA2000 (Petříček et al., 2000). The largest deviation from this symmetry concerns the fluoro- and the chlorophenyl rings whose planes contain 9.3 (1)°.

The weak hydrogen bonds of C—H···O and C—H···F are listed in Table 1. The weak intermolecular hydrogen bonds of C—H···O and C—H···F link the molecules (Fig. 2).

Related literature top

For related literature, see: Dzierzbicka et al. (2001); Hutchins et al. (2003); Kamal et al. (2004); Li et al. (2003); Petříček et al. (2000); Srivastava & Nizamuddin (2004); Wang et al. (2002, 2003).

Experimental top

The title compound was prepared by the reaction of 4-fluorobenzaldehyde (2 mmol, 0.248 g), 5,5-dimethyl-1,3-cyclohexanedione (2 mmol, 0.280 g) and 3-(4-chlorophenylamino)-5,5-dimethylcyclohex-2-enone (2 mmol, 0.498 g) in the ionic liquid of [Bmim]Br (1-butyl-3-methylimidazolium bromide) (10 ml) at 353 K. After the reaction had completed (monitored by TLC, about 6 h), the reactants were cooled to room temperature. The generated yellow solid was filtered off, and washed with small amount of water. The block crystals (about 0.2 mm in length, width and height respectively) suitable for X-ray diffraction were obtained by slow evaporation from ethanol solution. M.p. 583–585 K.

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear (Rigaku, 1999); data reduction: CrystalClear (Rigaku, 1999); 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: CrystalStructure (Rigaku/MSC, 2003).

Figures top

	Fig. 1. The title molecule with the displacement ellipsoids shown at the 50% probability level.
	Fig. 2. The molecular packing including the hydrogen-bonding network.

10-(4-Chlorophenyl)-9-(4-fluorophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10- hexahydroacridine-1,8(2H,5H)-dione top

Crystal data top

C₂₉H₂₉ClFNO₂	F(000) = 1008
M_r = 477.98	D_x = 1.260 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 583–585 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71070 Å
a = 12.0985 (12) Å	Cell parameters from 8097 reflections
b = 10.9001 (10) Å	θ = 1.7–27.9°
c = 19.4724 (18) Å	µ = 0.19 mm⁻¹
β = 101.231 (3)°	T = 113 K
V = 2518.7 (4) Å³	Block, yellow
Z = 4	0.32 × 0.20 × 0.18 mm

Data collection top

Rigaku Saturn diffractometer	6016 independent reflections
Radiation source: rotating anode	5436 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.040
Detector resolution: 14.63 pixels mm^-1	θ_max = 27.9°, θ_min = 1.7°
ω scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 1999)	k = −14→14
T_min = 0.943, T_max = 0.967	l = −25→25
30908 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.055	H-atom parameters constrained
wR(F²) = 0.137	w = 1/[σ²(F_o²) + (0.0579P)² + 1.0431P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
6016 reflections	Δρ_max = 0.42 e Å⁻³
312 parameters	Δρ_min = −0.45 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
112 constraints	Extinction coefficient: 0.0058 (9)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₉H₂₉ClFNO₂	V = 2518.7 (4) Å³
M_r = 477.98	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.0985 (12) Å	µ = 0.19 mm⁻¹
b = 10.9001 (10) Å	T = 113 K
c = 19.4724 (18) Å	0.32 × 0.20 × 0.18 mm
β = 101.231 (3)°

Data collection top

Rigaku Saturn diffractometer	6016 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 1999)	5436 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.967	R_int = 0.040
30908 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.10	Δρ_max = 0.42 e Å⁻³
6016 reflections	Δρ_min = −0.45 e Å⁻³
312 parameters

Special details top

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.

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
Cl1	0.86649 (5)	1.04288 (4)	0.25315 (3)	0.04213 (16)
F1	1.03322 (14)	0.02721 (16)	0.07820 (8)	0.0761 (5)
O1	0.56729 (11)	0.16766 (11)	0.17692 (7)	0.0326 (3)
O2	0.57270 (11)	0.31474 (12)	−0.06509 (7)	0.0330 (3)
N1	0.70646 (12)	0.56013 (12)	0.13279 (7)	0.0229 (3)
C1	0.67413 (13)	0.47215 (14)	0.17771 (8)	0.0219 (3)
C2	0.64094 (13)	0.35886 (15)	0.15353 (8)	0.0223 (3)
C3	0.64825 (14)	0.31701 (14)	0.08070 (9)	0.0231 (3)
H3	0.5793	0.2681	0.0614	0.028*
C4	0.65130 (13)	0.42790 (15)	0.03444 (9)	0.0231 (3)
C5	0.68642 (13)	0.53925 (14)	0.06063 (9)	0.0224 (3)
C6	0.74535 (14)	0.67913 (14)	0.16009 (8)	0.0228 (3)
C7	0.85853 (15)	0.69498 (17)	0.18908 (10)	0.0304 (4)
H7	0.9099	0.6289	0.1895	0.036*
C8	0.89647 (16)	0.80758 (18)	0.21746 (10)	0.0336 (4)
H8	0.9738	0.8194	0.2376	0.040*
C9	0.82031 (15)	0.90184 (16)	0.21587 (9)	0.0278 (4)
C10	0.70815 (15)	0.88861 (15)	0.18595 (9)	0.0269 (4)
H10	0.6576	0.9557	0.1844	0.032*
C11	0.67004 (14)	0.77543 (15)	0.15803 (9)	0.0244 (3)
H11	0.5927	0.7642	0.1376	0.029*
C12	0.67473 (15)	0.51183 (15)	0.25200 (9)	0.0263 (4)
H12A	0.6074	0.5631	0.2527	0.032*
H12B	0.7422	0.5631	0.2686	0.032*
C13	0.67515 (15)	0.40361 (15)	0.30251 (9)	0.0264 (4)
C14	0.58278 (15)	0.31382 (16)	0.26947 (9)	0.0274 (4)
H14A	0.5842	0.2417	0.3006	0.033*
H14B	0.5085	0.3541	0.2656	0.033*
C15	0.59618 (13)	0.27108 (15)	0.19831 (9)	0.0242 (3)
C16	0.65091 (19)	0.45153 (17)	0.37181 (10)	0.0365 (4)
H16A	0.5787	0.4952	0.3632	0.055*
H16B	0.7111	0.5077	0.3931	0.055*
H16C	0.6474	0.3825	0.4035	0.055*
C17	0.78922 (16)	0.33872 (18)	0.31572 (11)	0.0367 (4)
H17A	0.8487	0.3977	0.3342	0.055*
H17B	0.8031	0.3043	0.2717	0.055*
H17C	0.7890	0.2725	0.3497	0.055*
C18	0.70364 (15)	0.64547 (15)	0.01412 (9)	0.0263 (4)
H18A	0.7669	0.6965	0.0386	0.032*
H18B	0.6350	0.6970	0.0056	0.032*
C19	0.72913 (15)	0.60365 (16)	−0.05647 (9)	0.0276 (4)
C20	0.63778 (15)	0.51338 (17)	−0.08888 (9)	0.0293 (4)
H20A	0.5663	0.5589	−0.1036	0.035*
H20B	0.6584	0.4777	−0.1314	0.035*
C21	0.61825 (14)	0.41026 (16)	−0.04108 (9)	0.0264 (4)
C22	0.84573 (16)	0.54320 (18)	−0.04596 (10)	0.0338 (4)
H22A	0.8465	0.4697	−0.0168	0.051*
H22B	0.9029	0.6011	−0.0228	0.051*
H22C	0.8622	0.5201	−0.0916	0.051*
C23	0.72650 (17)	0.71613 (17)	−0.10400 (10)	0.0347 (4)
H23A	0.7434	0.6909	−0.1491	0.052*
H23B	0.7829	0.7758	−0.0818	0.052*
H23C	0.6515	0.7537	−0.1114	0.052*
C24	0.75157 (15)	0.23635 (15)	0.08100 (9)	0.0262 (4)
C25	0.85885 (16)	0.28331 (19)	0.10536 (10)	0.0350 (4)
H25	0.8671	0.3649	0.1227	0.042*
C26	0.95412 (18)	0.2128 (2)	0.10467 (11)	0.0443 (5)
H26	1.0274	0.2449	0.1214	0.053*
C27	0.9395 (2)	0.0961 (2)	0.07926 (11)	0.0480 (6)
C28	0.8360 (2)	0.0456 (2)	0.05529 (11)	0.0479 (6)
H28	0.8289	−0.0363	0.0382	0.057*
C29	0.74091 (18)	0.11699 (17)	0.05649 (10)	0.0357 (4)
H29	0.6680	0.0834	0.0403	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0539 (3)	0.0306 (3)	0.0401 (3)	−0.0193 (2)	0.0050 (2)	−0.00797 (19)
F1	0.0758 (10)	0.1001 (13)	0.0550 (9)	0.0666 (10)	0.0195 (8)	0.0108 (8)
O1	0.0356 (7)	0.0234 (6)	0.0404 (7)	−0.0077 (5)	0.0110 (6)	−0.0044 (5)
O2	0.0345 (7)	0.0322 (7)	0.0303 (7)	−0.0003 (5)	0.0012 (5)	−0.0087 (5)
N1	0.0274 (7)	0.0189 (6)	0.0234 (7)	−0.0022 (5)	0.0071 (5)	−0.0024 (5)
C1	0.0220 (8)	0.0207 (8)	0.0236 (8)	0.0005 (6)	0.0060 (6)	−0.0010 (6)
C2	0.0210 (8)	0.0212 (8)	0.0255 (8)	0.0014 (6)	0.0062 (6)	−0.0019 (6)
C3	0.0240 (8)	0.0199 (8)	0.0255 (8)	−0.0012 (6)	0.0051 (6)	−0.0040 (6)
C4	0.0214 (8)	0.0228 (8)	0.0249 (8)	0.0013 (6)	0.0042 (6)	−0.0019 (6)
C5	0.0215 (8)	0.0215 (8)	0.0248 (8)	0.0021 (6)	0.0058 (6)	−0.0007 (6)
C6	0.0272 (8)	0.0195 (8)	0.0225 (8)	−0.0033 (6)	0.0069 (6)	−0.0011 (6)
C7	0.0247 (9)	0.0297 (9)	0.0361 (10)	0.0017 (7)	0.0042 (7)	0.0027 (7)
C8	0.0251 (9)	0.0359 (10)	0.0374 (10)	−0.0087 (7)	0.0000 (7)	0.0017 (8)
C9	0.0338 (9)	0.0255 (8)	0.0242 (8)	−0.0101 (7)	0.0058 (7)	−0.0005 (7)
C10	0.0297 (9)	0.0215 (8)	0.0310 (9)	−0.0012 (7)	0.0093 (7)	−0.0027 (7)
C11	0.0231 (8)	0.0227 (8)	0.0281 (8)	−0.0023 (6)	0.0065 (6)	−0.0025 (6)
C12	0.0355 (9)	0.0201 (8)	0.0248 (8)	−0.0015 (7)	0.0097 (7)	−0.0032 (6)
C13	0.0335 (9)	0.0199 (8)	0.0253 (8)	−0.0007 (7)	0.0046 (7)	−0.0001 (6)
C14	0.0311 (9)	0.0244 (8)	0.0282 (9)	−0.0023 (7)	0.0091 (7)	0.0014 (7)
C15	0.0203 (8)	0.0207 (8)	0.0314 (9)	0.0002 (6)	0.0044 (6)	−0.0022 (6)
C16	0.0572 (13)	0.0263 (9)	0.0267 (9)	−0.0019 (8)	0.0100 (8)	0.0006 (7)
C17	0.0349 (10)	0.0314 (10)	0.0394 (11)	0.0016 (8)	−0.0038 (8)	−0.0039 (8)
C18	0.0303 (9)	0.0230 (8)	0.0268 (9)	0.0019 (7)	0.0084 (7)	0.0003 (7)
C19	0.0307 (9)	0.0282 (9)	0.0249 (8)	0.0044 (7)	0.0081 (7)	0.0028 (7)
C20	0.0307 (9)	0.0318 (9)	0.0243 (8)	0.0053 (7)	0.0028 (7)	0.0005 (7)
C21	0.0217 (8)	0.0286 (9)	0.0283 (9)	0.0059 (7)	0.0039 (6)	−0.0034 (7)
C22	0.0292 (9)	0.0388 (10)	0.0356 (10)	0.0058 (8)	0.0121 (8)	0.0053 (8)
C23	0.0415 (11)	0.0330 (10)	0.0309 (10)	0.0053 (8)	0.0106 (8)	0.0067 (8)
C24	0.0332 (9)	0.0248 (8)	0.0221 (8)	0.0069 (7)	0.0096 (7)	0.0026 (6)
C25	0.0299 (10)	0.0371 (10)	0.0395 (11)	0.0063 (8)	0.0107 (8)	0.0043 (8)
C26	0.0334 (11)	0.0602 (14)	0.0423 (12)	0.0169 (10)	0.0146 (9)	0.0142 (10)
C27	0.0546 (14)	0.0618 (15)	0.0310 (10)	0.0382 (12)	0.0168 (9)	0.0116 (10)
C28	0.0770 (17)	0.0372 (11)	0.0303 (11)	0.0299 (11)	0.0124 (10)	−0.0012 (8)
C29	0.0515 (12)	0.0278 (9)	0.0273 (9)	0.0104 (8)	0.0058 (8)	−0.0018 (7)

Geometric parameters (Å, º) top

Cl1—C9	1.7449 (18)	C14—H14A	0.9900
F1—C27	1.364 (2)	C14—H14B	0.9900
O1—C15	1.229 (2)	C16—H16A	0.9800
O2—C21	1.227 (2)	C16—H16B	0.9800
N1—C5	1.397 (2)	C16—H16C	0.9800
N1—C1	1.404 (2)	C17—H17A	0.9800
N1—C6	1.445 (2)	C17—H17B	0.9800
C1—C2	1.354 (2)	C17—H17C	0.9800
C1—C12	1.509 (2)	C18—C19	1.535 (2)
C2—C15	1.467 (2)	C18—H18A	0.9900
C2—C3	1.509 (2)	C18—H18B	0.9900
C3—C4	1.512 (2)	C19—C20	1.522 (3)
C3—C24	1.527 (2)	C19—C23	1.533 (2)
C3—H3	1.0000	C19—C22	1.534 (2)
C4—C5	1.353 (2)	C20—C21	1.507 (3)
C4—C21	1.460 (2)	C20—H20A	0.9900
C5—C18	1.509 (2)	C20—H20B	0.9900
C6—C11	1.385 (2)	C22—H22A	0.9800
C6—C7	1.387 (2)	C22—H22B	0.9800
C7—C8	1.387 (3)	C22—H22C	0.9800
C7—H7	0.9500	C23—H23A	0.9800
C8—C9	1.376 (3)	C23—H23B	0.9800
C8—H8	0.9500	C23—H23C	0.9800
C9—C10	1.376 (2)	C24—C29	1.383 (2)
C10—C11	1.390 (2)	C24—C25	1.390 (3)
C10—H10	0.9500	C25—C26	1.388 (3)
C11—H11	0.9500	C25—H25	0.9500
C12—C13	1.535 (2)	C26—C27	1.364 (3)
C12—H12A	0.9900	C26—H26	0.9500
C12—H12B	0.9900	C27—C28	1.364 (4)
C13—C17	1.527 (2)	C28—C29	1.393 (3)
C13—C16	1.528 (2)	C28—H28	0.9500
C13—C14	1.530 (2)	C29—H29	0.9500
C14—C15	1.500 (2)

C5—N1—C1	120.03 (13)	H16A—C16—H16B	109.5
C5—N1—C6	119.75 (13)	C13—C16—H16C	109.5
C1—N1—C6	119.62 (13)	H16A—C16—H16C	109.5
C2—C1—N1	120.39 (15)	H16B—C16—H16C	109.5
C2—C1—C12	122.73 (15)	C13—C17—H17A	109.5
N1—C1—C12	116.85 (13)	C13—C17—H17B	109.5
C1—C2—C15	120.44 (15)	H17A—C17—H17B	109.5
C1—C2—C3	122.33 (15)	C13—C17—H17C	109.5
C15—C2—C3	117.23 (14)	H17A—C17—H17C	109.5
C2—C3—C4	109.33 (13)	H17B—C17—H17C	109.5
C2—C3—C24	111.60 (13)	C5—C18—C19	112.63 (14)
C4—C3—C24	110.34 (13)	C5—C18—H18A	109.1
C2—C3—H3	108.5	C19—C18—H18A	109.1
C4—C3—H3	108.5	C5—C18—H18B	109.1
C24—C3—H3	108.5	C19—C18—H18B	109.1
C5—C4—C21	120.15 (15)	H18A—C18—H18B	107.8
C5—C4—C3	122.35 (15)	C20—C19—C23	109.80 (15)
C21—C4—C3	117.47 (14)	C20—C19—C22	110.63 (15)
C4—C5—N1	120.36 (15)	C23—C19—C22	109.55 (15)
C4—C5—C18	122.15 (15)	C20—C19—C18	107.87 (14)
N1—C5—C18	117.48 (14)	C23—C19—C18	108.60 (14)
C11—C6—C7	120.61 (15)	C22—C19—C18	110.36 (14)
C11—C6—N1	120.28 (14)	C21—C20—C19	114.50 (14)
C7—C6—N1	119.11 (15)	C21—C20—H20A	108.6
C6—C7—C8	119.77 (17)	C19—C20—H20A	108.6
C6—C7—H7	120.1	C21—C20—H20B	108.6
C8—C7—H7	120.1	C19—C20—H20B	108.6
C9—C8—C7	118.91 (16)	H20A—C20—H20B	107.6
C9—C8—H8	120.5	O2—C21—C4	120.67 (16)
C7—C8—H8	120.5	O2—C21—C20	120.69 (16)
C10—C9—C8	122.13 (16)	C4—C21—C20	118.61 (15)
C10—C9—Cl1	118.55 (14)	C19—C22—H22A	109.5
C8—C9—Cl1	119.32 (14)	C19—C22—H22B	109.5
C9—C10—C11	118.90 (16)	H22A—C22—H22B	109.5
C9—C10—H10	120.6	C19—C22—H22C	109.5
C11—C10—H10	120.6	H22A—C22—H22C	109.5
C6—C11—C10	119.66 (15)	H22B—C22—H22C	109.5
C6—C11—H11	120.2	C19—C23—H23A	109.5
C10—C11—H11	120.2	C19—C23—H23B	109.5
C1—C12—C13	113.13 (13)	H23A—C23—H23B	109.5
C1—C12—H12A	109.0	C19—C23—H23C	109.5
C13—C12—H12A	109.0	H23A—C23—H23C	109.5
C1—C12—H12B	109.0	H23B—C23—H23C	109.5
C13—C12—H12B	109.0	C29—C24—C25	118.83 (17)
H12A—C12—H12B	107.8	C29—C24—C3	121.26 (16)
C17—C13—C16	109.41 (15)	C25—C24—C3	119.90 (15)
C17—C13—C14	109.67 (14)	C26—C25—C24	121.0 (2)
C16—C13—C14	109.88 (15)	C26—C25—H25	119.5
C17—C13—C12	110.72 (15)	C24—C25—H25	119.5
C16—C13—C12	109.02 (14)	C27—C26—C25	118.1 (2)
C14—C13—C12	108.12 (14)	C27—C26—H26	121.0
C15—C14—C13	112.68 (14)	C25—C26—H26	121.0
C15—C14—H14A	109.1	F1—C27—C26	118.0 (2)
C13—C14—H14A	109.1	F1—C27—C28	118.9 (2)
C15—C14—H14B	109.1	C26—C27—C28	123.11 (19)
C13—C14—H14B	109.1	C27—C28—C29	118.3 (2)
H14A—C14—H14B	107.8	C27—C28—H28	120.8
O1—C15—C2	120.69 (16)	C29—C28—H28	120.8
O1—C15—C14	121.55 (15)	C24—C29—C28	120.6 (2)
C2—C15—C14	117.72 (14)	C24—C29—H29	119.7
C13—C16—H16A	109.5	C28—C29—H29	119.7
C13—C16—H16B	109.5

C5—N1—C1—C2	11.0 (2)	C1—C12—C13—C17	71.36 (18)
C6—N1—C1—C2	−177.87 (14)	C1—C12—C13—C16	−168.23 (15)
C5—N1—C1—C12	−166.96 (14)	C1—C12—C13—C14	−48.81 (19)
C6—N1—C1—C12	4.1 (2)	C17—C13—C14—C15	−64.45 (19)
N1—C1—C2—C15	−173.71 (14)	C16—C13—C14—C15	175.25 (14)
C12—C1—C2—C15	4.2 (2)	C12—C13—C14—C15	56.38 (19)
N1—C1—C2—C3	6.5 (2)	C1—C2—C15—O1	−179.08 (15)
C12—C1—C2—C3	−175.64 (15)	C3—C2—C15—O1	0.7 (2)
C1—C2—C3—C4	−22.1 (2)	C1—C2—C15—C14	3.3 (2)
C15—C2—C3—C4	158.08 (14)	C3—C2—C15—C14	−176.84 (14)
C1—C2—C3—C24	100.24 (18)	C13—C14—C15—O1	147.61 (16)
C15—C2—C3—C24	−79.58 (18)	C13—C14—C15—C2	−34.8 (2)
C2—C3—C4—C5	23.5 (2)	C4—C5—C18—C19	−25.5 (2)
C24—C3—C4—C5	−99.62 (18)	N1—C5—C18—C19	155.53 (14)
C2—C3—C4—C21	−158.60 (14)	C5—C18—C19—C20	52.13 (18)
C24—C3—C4—C21	78.30 (18)	C5—C18—C19—C23	171.08 (15)
C21—C4—C5—N1	173.05 (14)	C5—C18—C19—C22	−68.83 (19)
C3—C4—C5—N1	−9.1 (2)	C23—C19—C20—C21	−169.46 (14)
C21—C4—C5—C18	−5.9 (2)	C22—C19—C20—C21	69.51 (19)
C3—C4—C5—C18	171.93 (15)	C18—C19—C20—C21	−51.28 (19)
C1—N1—C5—C4	−9.7 (2)	C5—C4—C21—O2	−170.52 (16)
C6—N1—C5—C4	179.21 (15)	C3—C4—C21—O2	11.5 (2)
C1—N1—C5—C18	169.32 (14)	C5—C4—C21—C20	7.5 (2)
C6—N1—C5—C18	−1.8 (2)	C3—C4—C21—C20	−170.44 (14)
C5—N1—C6—C11	79.2 (2)	C19—C20—C21—O2	−159.05 (16)
C1—N1—C6—C11	−91.90 (19)	C19—C20—C21—C4	22.9 (2)
C5—N1—C6—C7	−101.61 (19)	C2—C3—C24—C29	120.14 (17)
C1—N1—C6—C7	87.3 (2)	C4—C3—C24—C29	−118.09 (17)
C11—C6—C7—C8	1.2 (3)	C2—C3—C24—C25	−60.7 (2)
N1—C6—C7—C8	−177.99 (16)	C4—C3—C24—C25	61.0 (2)
C6—C7—C8—C9	−0.3 (3)	C29—C24—C25—C26	0.6 (3)
C7—C8—C9—C10	−1.2 (3)	C3—C24—C25—C26	−178.51 (17)
C7—C8—C9—Cl1	178.58 (14)	C24—C25—C26—C27	0.1 (3)
C8—C9—C10—C11	1.7 (3)	C25—C26—C27—F1	179.58 (18)
Cl1—C9—C10—C11	−178.07 (13)	C25—C26—C27—C28	−0.7 (3)
C7—C6—C11—C10	−0.7 (3)	F1—C27—C28—C29	−179.85 (18)
N1—C6—C11—C10	178.50 (15)	C26—C27—C28—C29	0.4 (3)
C9—C10—C11—C6	−0.7 (3)	C25—C24—C29—C28	−0.9 (3)
C2—C1—C12—C13	20.1 (2)	C3—C24—C29—C28	178.23 (16)
N1—C1—C12—C13	−161.93 (14)	C27—C28—C29—C24	0.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16C···O2ⁱ	0.98	2.45	3.359 (2)	153
C11—H11···O2ⁱⁱ	0.95	2.37	3.286 (2)	160
C10—H10···O1ⁱⁱⁱ	0.95	2.55	3.474 (2)	165
C16—H16A···O1^iv	0.98	2.59	3.528 (2)	159
C17—H17A···F1^v	0.98	2.45	3.373 (2)	157

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

Experimental details

Crystal data
Chemical formula	C₂₉H₂₉ClFNO₂
M_r	477.98
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	12.0985 (12), 10.9001 (10), 19.4724 (18)
β (°)	101.231 (3)
V (Å³)	2518.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.32 × 0.20 × 0.18

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 1999)
T_min, T_max	0.943, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	30908, 6016, 5436
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.137, 1.10
No. of reflections	6016
No. of parameters	312
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.45

Computer programs: CrystalClear (Rigaku, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16C···O2ⁱ	0.98	2.45	3.359 (2)	153.3
C11—H11···O2ⁱⁱ	0.95	2.37	3.286 (2)	160.4
C10—H10···O1ⁱⁱⁱ	0.95	2.55	3.474 (2)	165.1
C16—H16A···O1^iv	0.98	2.59	3.528 (2)	159.3
C17—H17A···F1^v	0.98	2.45	3.373 (2)	157.1

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

Acknowledgements

The authors are grateful to the Natural Science Foundation of Xuzhou Normal University (grant Nos. 06AXL10 and 06PYL04) and to the Natural Science Foundation of the Education Committee of Jiangsu Province (grant No. 04KJB150139) for financial support.

References

Dzierzbicka, K., Kolodziejczyk, A. M., Wysocka-Skrzela, B., Mysliwski, A. & Sosnowska, D. (2001). J. Med. Chem. 44, 3606–3615. Web of Science CrossRef PubMed CAS Google Scholar
Hutchins, R. A., Crenshaw, J. M., Graves, D. E. & Denny, W. A. (2003). Biochemistry, 42, 13754–13761. Web of Science CrossRef PubMed CAS Google Scholar
Kamal, A., Srinivas, O., Ramulu, P., Ramesh, G. & Kumar, P. P. (2004). Bioorg. Med. Chem. Lett. 14, 4107–4111. Web of Science CrossRef PubMed CAS Google Scholar
Li, Y., Wang, X., Shi, D., Du, B. & Tu, S. (2003). Acta Cryst. E59, o1446–o1448. Web of Science CSD CrossRef IUCr Journals Google Scholar
Petříček, V., Dušek, M. & Palatinus, L. (2000). JANA2000. Institute of Physics, Czech Academy of Science, Czech Republic. Google Scholar
Rigaku (1999). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2003). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Srivastava, A. & Nizamuddin, C. (2004). Indian J. Heterocycl. Chem. 13, 261–264. CAS Google Scholar
Wang, X., Shi, D. & Tu, S. (2003). Acta Cryst. E59, o1139–o1140. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Wang, X. S., Shi, D. Q., Tu, S. J., Yao, C. S. & Wang, Y. C. (2002). Chin. J. Struct. Chem. 21, 146–149. CAS Google Scholar

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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 9| September 2008| Pages o1772-o1773

doi:10.1107/S1600536808025695

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

10-(4-Chloro­phen­yl)-9-(4-fluoro­phen­yl)-3,3,6,6-tetra­methyl-3,4,6,7,9,10-hexa­hydro­acridine-1,8(2H,5H)-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

10-(4-Chlorophenyl)-9-(4-fluorophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione