10-(4-Fluorophenyl)-3,3,6,6,9-pentamethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione and 10-(4-fluorophenyl)-3,3,6,6-tetramethyl-9-­propyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione

10-(4-Fluoro­phenyl)-3,3,6,6,9-penta­methyl-3,4,6,7,9,10-hexa­hydro­acridine-1,8(2H,5H)-dione, C₂₄H₂₈FNO₂, (I), crystallizes with two crystallographically independent mol­ecules (which differ slightly in conformation), while 10-(4-fluoro­phenyl)-9-propyl-3,3,6,6-tetra­methyl-3,4,6,7,9,10-hexa­hydro­acridine-1,8(2H,5H)-dione, C₂₆H₃₂FNO₂, (II), crystallizes with one mol­ecule per asymmetric unit. In both structures, the central ring in the acridine moiety is in a sofa conformation, while the outer rings adopt intermediate half-chair/sofa conformations. The central pyridine ring is orthogonal to the substituted phenyl ring. In both structures, the packing of the crystal is stabilized by C—H...O intermolecular hydrogen bonds.

S1. Comment

Acridine and its derivatives exhibit a wide spectrum of biological activities, such as antibacterial (Acheson et al., 1956), mutagenic and antitumour (Talacki et al., 1974), and antiamoebic (Prasad Krishna et al., 1984). The potency of acridines as antiviral and antibacterial agents is due to their ability to bind DNA by intercalation (Neidle, 1979; Nandi et al., 1990). Substitutions at C9 and N10 make the central ring of acridine buckled along the C9···N10 direction, with a dihedral angle formed by the two halves ranging from 7 to 13°. These values are smaller than those found in the present work. This buckling was postulated as the cause of their biological properties by Glusker et al. (1972). In acridine-1,8-diones, the electron delocalization is along a stretch of nine non-H atoms (O1 ═ C1—C13═C14—N10—C11═C12—C8═O2) which facilitate the exhibition of fluorescence and laser activity (Selladurai et al., 1990). The effectiveness of this laser activity can be controlled by the substituents at the 9- and 10-positions of the acridine chromophore. The decahydroacridine-1,8-diones act as photo-sensitizers (Timpe et al., 1993). Acridinediones have also been found to act as laser dyes, acting at around 475–495 nm (Murugan et al., 1998). The present study of the title compounds, (I) and (II), is a part of a series of investigations on the crystal structures of acridinedione derivatives. \sch

Compound (I) has two molecules in the asymmetric unit, designated (Ia) and (Ib). Fig. 1 shows the molecular structure and the atom-labelling scheme for both (Ia) and (Ib). Compound (II) has one molecule per asymmetric unit and Fig. 2 shows the molecular structure and atom-labelling scheme for (II).

The bond lengths C═O and Csp²—F in both structures are comparable with the values found in the literature (Allen et al., 1987). The average C═O [1.224 (3) Å in (Ia), 1.233 (3) Å in (Ib) and 1.228 (3) Å in (II)] and N—C [1.417 (3) Å in (Ia), 1.418 (2) Å in (Ib) and 1.415 (3) Å in (II)] bond lengths agree well with the values in several related structures (Jeyakanthan et al., 2000; Gunasekaran et al., 1996; Britto-Arias et al., 1996). Selected geometric parameters are given in Tables 1 and 3.

The acridine moiety is folded about the line passing through atoms C9 and N10, and the dihedral angle between the two halves is 27.4 (1)° in (Ia), 18.8 (1)° in (Ib) and 21.5 (1)° in (II). These values compare well with those reported in similar acridine derivatives (Gunasekaran et al., 1996; Sivaraman et al., 1994, 1996). The dihedral angle between the outer rings A and C of the acridine moiety is 18.0 (1)° in (Ia), 9.1 (1)° in (Ib) and 15.0 (1)° in (II) and this shows considerable buckling of the acridine nucleus.

The phenyl ring D in both structures is orthogonal to the central ring B, forming a dihedral angle of 88.3 (1)° in (Ia), 87.1 (1)° in (Ib) and 87.5 (1)° in (II). The valence angles around the N atom in both structures sum to 359.8 (2)° in (Ia), 359.0 (2)° in (Ib) and 358.9 (2)° in (II), and these values are indicative of sp² hybridization of the nitrogen.

The C25A and C25B methyls in (I) and the C25 propyl in (II) are axial, as indicated by the angles formed by the C9—C25 and C9—H9 bonds with the plane through O1/C1/C13/C14/C11/C12/C8/O2 [C9A—C25A 88.1, C9A—H9A 21, C9B—C25B 77.6 and C9B—H9B 30° in (I), and C9—C25 79.7 and C9—H9 18° in (II)]. The deviation of atoms O1 and O2 from the mean planes passing through rings A and C are 0.144 (3) and 0.175 (2) Å in (Ia), 0.022 (2) and 0.098 (2) Å in (Ib) and 0.018 (2) and 0.101 (2) Å in (II), respectively.

The puckering amplitudes (Cremer & Pople, 1975) of the rings in the acridine moiety (Table 5) agree well with those of related structures (Gunasekaran et al., 1997; Jeyakanthan et al., 2000). The conformations of the rings of the acridine moiety in both structures are defined by the asymmetry parameters (Nardelli, 1983a), also given in Table 5.

In addition to the normal van der Waals interactions, the packing of the crystals in both structures is stabilized by C—H···O intermolecular hydrogen bonds. In (I), an intermolecular C—H···O hydrogen bond joins the molecules in a chain along the b direction. In (II), four C—H···O interactions occur with H···O distances less than the sum of the van der Waals radii (Bondi, 1964) (Table 4). In this structure, the acridine molecules are stacked in a head-to-head manner (Dauter et al., 1976) and are alternately parallel to each other. This type of stacking is also found in acridinedione (Sivaraman et al., 1996) and 9-amino acridine structures (Talacki et al., 1974).

S2. Experimental

The title compounds were synthesized as follows. A mixture of 2,2'-ethylidenebis(5,5-dimethylcyclohexane-1,3-dione) (2 g, 6.5 mmol) and 4-fluoroaniline (0.63 ml, 6.5 mmol) for compound (I), and a mixture of 2,2'-butylidenebis(5,5-dimethylcyclohexane-1,3-dione) (2 g, 6.0 mmol) and 4-fluoroaniline (0.60 ml, 6.0 mmol) for compound (II), were taken as starting materials. The reaction mixtures were refluxed in acetic acid (25 ml) for 7 h, after which time they were concentrated and poured onto ice. The yellow solids obtained were filtered and dried to afford the title compounds in yields of 1.8 g (72.3%) for (I) and 1.75 g (71.3%) for (II). The compounds were dissolved in a mixture of chloroform and methanol (2:1). Slow evaporation of the solvent at room temperature produced crystals of (I) and (II) suitable for X-ray analysis.

S3. Refinement

Please provide brief details of H-atom refinement.

Computing details

Data collection: SMART (Siemens, 1996) for (I); CAD-4 Software (Enraf-Nonius, 1989) for (II). Cell refinement: SAINT (Siemens, 1996) for (I); CAD-4 Software for (II). Data reduction: SAINT for (I); SDP (Frenz, 1985) for (II). For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1983b, 1995).

Figures

	Fig. 1. The molecular structure of the two independent molecules of (I) with the atom-labelling scheme and 30% probability displacement ellipsoids. H atoms are displayed as small spheres of arbitrary radii.
	Fig. 2. The molecular structure of (II) with the atom-labelling scheme and 30% probability displacement ellipsoids. H atoms are displayed as small spheres of arbitrary radii.

(I) 10-(4-Fluorophenyl)-3,3,6,6,9-pentamethyl-3,4,6,7,9,10-hexahydroacridine- 1,8(2H,5H)-dione

Crystal data

C24H28FNO2	F(000) = 1632
Mr = 381.47	Dx = 1.167 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.1481 (2) Å	Cell parameters from 8324 reflections
b = 17.3909 (1) Å	θ = 1.3–28.3°
c = 15.8023 (3) Å	µ = 0.08 mm^−1
β = 112.849 (1)°	T = 293 K
V = 4342.79 (10) Å^3	Block, pale yellow
Z = 8	0.48 × 0.38 × 0.28 mm

Data collection

Siemens SMART CCD area-detector diffractometer	10547 independent reflections
Radiation source: fine-focus sealed tube	4439 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
Detector resolution: 8.33 pixels mm^-1	θmax = 28.3°, θmin = 1.3°
ω scans	h = −22→22
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −23→20
Tmin = 0.963, Tmax = 0.978	l = −20→21
29750 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.188	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0504P)^2 + 0.0465P] where P = (Fo^2 + 2Fc^2)/3
10547 reflections	(Δ/σ)max = 0.001
505 parameters	Δρmax = 0.72 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F1A	0.13594 (12)	0.48518 (11)	0.62816 (10)	0.1049 (6)
O1A	−0.04953 (16)	0.19049 (14)	0.05127 (15)	0.1204 (9)
O2A	0.21222 (15)	0.32224 (12)	0.06847 (14)	0.1017 (8)
C1A	−0.0312 (2)	0.20976 (19)	0.1306 (2)	0.0937 (10)
C2A	−0.0707 (3)	0.1713 (2)	0.1906 (2)	0.1371 (17)
H2A1	−0.1256	0.1512	0.1511	0.164*
H2A2	−0.0356	0.1278	0.2212	0.164*
C3A	−0.0820 (2)	0.2205 (2)	0.2609 (2)	0.0919 (10)
C4A	−0.00306 (19)	0.26358 (17)	0.31629 (18)	0.0843 (9)
H4A1	0.0338	0.2300	0.3641	0.101*
H4A2	−0.0179	0.3068	0.3459	0.101*
C5A	0.25277 (15)	0.39325 (13)	0.33123 (15)	0.0542 (6)
H5A1	0.2864	0.3538	0.3728	0.065*
H5A2	0.2410	0.4329	0.3678	0.065*
C6A	0.30431 (15)	0.42835 (12)	0.28041 (15)	0.0508 (6)
C7A	0.30978 (17)	0.36812 (13)	0.21246 (17)	0.0638 (7)
H7A1	0.3400	0.3898	0.1774	0.077*
H7A2	0.3418	0.3243	0.2463	0.077*
C8A	0.22443 (19)	0.34141 (14)	0.14764 (18)	0.0669 (7)
C9A	0.06903 (19)	0.31306 (17)	0.11792 (17)	0.0757 (8)
H9A	0.0736	0.2776	0.0718	0.091*
N10A	0.10945 (12)	0.34586 (10)	0.30430 (12)	0.0529 (5)
C11A	0.17107 (15)	0.35877 (12)	0.26816 (15)	0.0489 (6)
C12A	0.15673 (16)	0.33728 (13)	0.18143 (15)	0.0580 (6)
C13A	0.02875 (17)	0.27178 (15)	0.17348 (17)	0.0693 (7)
C14A	0.04458 (16)	0.29298 (14)	0.26059 (16)	0.0615 (7)
C15A	−0.1479 (3)	0.2855 (3)	0.2019 (3)	0.171 (2)
H15A	−0.2001	0.2616	0.1634	0.257*
H15B	−0.1244	0.3127	0.1644	0.257*
H15C	−0.1584	0.3210	0.2428	0.257*
C16A	−0.1222 (2)	0.1842 (2)	0.3200 (2)	0.1227 (14)
H16A	−0.1725	0.1573	0.2819	0.184*
H16B	−0.1366	0.2233	0.3542	0.184*
H16C	−0.0832	0.1486	0.3617	0.184*
C17A	0.26336 (18)	0.50188 (13)	0.23096 (18)	0.0704 (7)
H17A	0.2607	0.5388	0.2749	0.106*
H17B	0.2072	0.4908	0.1877	0.106*
H17C	0.2963	0.5224	0.1991	0.106*
C18A	0.39378 (16)	0.44616 (14)	0.35001 (18)	0.0683 (7)
H18A	0.3909	0.4841	0.3928	0.102*
H18B	0.4274	0.4655	0.3183	0.102*
H18C	0.4191	0.4001	0.3825	0.102*
C19A	0.11745 (14)	0.38134 (13)	0.39024 (14)	0.0485 (5)
C20A	0.08155 (16)	0.45255 (13)	0.38764 (16)	0.0578 (6)
H20A	0.0527	0.4768	0.3317	0.069*
C21A	0.08855 (17)	0.48780 (15)	0.46870 (19)	0.0686 (7)
H21A	0.0649	0.5360	0.4682	0.082*
C22A	0.13082 (18)	0.45028 (17)	0.54920 (17)	0.0669 (7)
C23A	0.16696 (18)	0.38007 (17)	0.55324 (17)	0.0709 (7)
H23A	0.1956	0.3560	0.6094	0.085*
C24A	0.16023 (16)	0.34540 (14)	0.47259 (15)	0.0588 (6)
H24A	0.1847	0.2975	0.4738	0.071*
C25A	0.0171 (2)	0.3831 (2)	0.0690 (2)	0.1142 (12)
H25A	−0.0380	0.3667	0.0277	0.171*
H25B	0.0452	0.4087	0.0349	0.171*
H25C	0.0117	0.4178	0.1135	0.171*
F1B	0.27680 (11)	0.57834 (10)	0.45252 (9)	0.0968 (6)
O1B	0.41827 (13)	0.50994 (11)	1.11475 (11)	0.0866 (6)
O2B	0.57048 (15)	0.74826 (11)	1.09019 (11)	0.0950 (7)
C1B	0.38697 (17)	0.50616 (15)	1.03059 (17)	0.0636 (7)
C2B	0.34041 (19)	0.43501 (15)	0.98335 (17)	0.0740 (8)
H2B1	0.3127	0.4126	1.0206	0.089*
H2B2	0.3812	0.3979	0.9797	0.089*
C3B	0.27400 (18)	0.44897 (14)	0.88664 (17)	0.0667 (7)
C4B	0.31815 (16)	0.49122 (14)	0.83246 (15)	0.0623 (7)
H4B1	0.3558	0.4557	0.8196	0.075*
H4B2	0.2758	0.5078	0.7741	0.075*
C5B	0.47969 (16)	0.71803 (12)	0.80993 (15)	0.0569 (6)
H5B1	0.4333	0.7281	0.7517	0.068*
H5B2	0.5211	0.6870	0.7975	0.068*
C6B	0.52057 (17)	0.79446 (12)	0.85185 (15)	0.0592 (7)
C7B	0.58246 (18)	0.77902 (14)	0.94911 (15)	0.0678 (7)
H7B1	0.6288	0.7481	0.9471	0.081*
H7B2	0.6058	0.8275	0.9783	0.081*
C8B	0.54295 (18)	0.73831 (13)	1.00602 (15)	0.0650 (7)
C9B	0.43613 (17)	0.64231 (14)	1.01983 (15)	0.0601 (7)
H9B	0.4820	0.6291	1.0783	0.072*
N10B	0.38747 (12)	0.61528 (10)	0.82829 (11)	0.0480 (5)
C11B	0.44670 (15)	0.67302 (11)	0.87033 (14)	0.0467 (5)
C12B	0.47461 (16)	0.68423 (12)	0.96164 (14)	0.0526 (6)
C13B	0.39633 (15)	0.56911 (13)	0.97379 (14)	0.0528 (6)
C14B	0.36831 (14)	0.56006 (12)	0.88194 (14)	0.0479 (5)
C18B	0.5680 (2)	0.82851 (15)	0.79618 (17)	0.0864 (9)
H18D	0.5288	0.8382	0.7345	0.130*
H18E	0.6104	0.7929	0.7953	0.130*
H18F	0.5945	0.8759	0.8238	0.130*
C17B	0.4532 (2)	0.85122 (16)	0.8533 (2)	0.0985 (11)
H17D	0.4135	0.8602	0.7917	0.148*
H17E	0.4796	0.8989	0.8801	0.148*
H17F	0.4241	0.8303	0.8891	0.148*
C16B	0.2403 (2)	0.37132 (17)	0.84113 (19)	0.0974 (11)
H16D	0.2125	0.3452	0.8752	0.146*
H16E	0.2865	0.3405	0.8405	0.146*
H16F	0.2007	0.3796	0.7793	0.146*
C15B	0.20056 (19)	0.49684 (19)	0.8898 (2)	0.0939 (10)
H15D	0.1736	0.4697	0.9239	0.141*
H15E	0.1603	0.5057	0.8284	0.141*
H15F	0.2216	0.5452	0.9190	0.141*
C19B	0.35848 (14)	0.60444 (12)	0.72964 (13)	0.0444 (5)
C20B	0.28648 (15)	0.64148 (14)	0.67204 (15)	0.0587 (6)
H20B	0.2566	0.6727	0.6968	0.070*
C21B	0.25804 (16)	0.63282 (14)	0.57779 (15)	0.0632 (7)
H21B	0.2095	0.6578	0.5386	0.076*
C22B	0.30327 (17)	0.58668 (14)	0.54457 (14)	0.0590 (6)
C23B	0.37488 (17)	0.54952 (14)	0.59984 (16)	0.0617 (7)
H23B	0.4046	0.5187	0.5745	0.074*
C24B	0.40297 (15)	0.55817 (13)	0.69396 (15)	0.0541 (6)
H24B	0.4515	0.5329	0.7327	0.065*
C25B	0.3734 (2)	0.69308 (18)	1.0408 (2)	0.0953 (10)
H25D	0.4014	0.7391	1.0712	0.143*
H25E	0.3518	0.6657	1.0798	0.143*
H25F	0.3275	0.7064	0.9845	0.143*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1A	0.1169 (15)	0.1396 (15)	0.0615 (10)	−0.0050 (11)	0.0383 (10)	−0.0366 (10)
O1A	0.135 (2)	0.142 (2)	0.0807 (15)	−0.0678 (16)	0.0380 (15)	−0.0541 (14)
O2A	0.141 (2)	0.1099 (16)	0.0813 (14)	−0.0488 (14)	0.0735 (15)	−0.0463 (12)
C1A	0.099 (3)	0.106 (2)	0.070 (2)	−0.0447 (19)	0.0257 (18)	−0.0282 (18)
C2A	0.159 (4)	0.144 (3)	0.103 (3)	−0.099 (3)	0.045 (3)	−0.034 (3)
C3A	0.083 (2)	0.119 (3)	0.081 (2)	−0.056 (2)	0.0391 (19)	−0.031 (2)
C4A	0.088 (2)	0.098 (2)	0.0657 (18)	−0.0433 (17)	0.0293 (16)	−0.0102 (15)
C5A	0.0563 (16)	0.0584 (14)	0.0478 (13)	−0.0097 (11)	0.0201 (12)	−0.0057 (11)
C6A	0.0588 (16)	0.0428 (12)	0.0557 (14)	−0.0031 (10)	0.0277 (12)	−0.0013 (10)
C7A	0.077 (2)	0.0546 (15)	0.0741 (17)	0.0004 (12)	0.0444 (16)	−0.0023 (13)
C8A	0.099 (2)	0.0546 (15)	0.0617 (16)	−0.0160 (14)	0.0474 (16)	−0.0139 (13)
C9A	0.086 (2)	0.094 (2)	0.0487 (14)	−0.0264 (16)	0.0277 (15)	−0.0183 (14)
N10A	0.0590 (13)	0.0580 (12)	0.0439 (11)	−0.0181 (9)	0.0223 (10)	−0.0102 (9)
C11A	0.0584 (16)	0.0432 (12)	0.0460 (13)	−0.0073 (10)	0.0212 (12)	−0.0042 (10)
C12A	0.0715 (18)	0.0561 (14)	0.0473 (14)	−0.0129 (12)	0.0239 (13)	−0.0098 (11)
C13A	0.0723 (19)	0.0778 (18)	0.0526 (15)	−0.0292 (14)	0.0187 (14)	−0.0161 (13)
C14A	0.0632 (18)	0.0643 (15)	0.0547 (15)	−0.0226 (12)	0.0204 (13)	−0.0095 (12)
C15A	0.076 (3)	0.273 (6)	0.157 (4)	0.014 (3)	0.037 (3)	0.052 (4)
C16A	0.111 (3)	0.150 (3)	0.100 (3)	−0.074 (3)	0.033 (2)	0.000 (2)
C17A	0.088 (2)	0.0474 (14)	0.0771 (18)	−0.0021 (13)	0.0332 (16)	0.0060 (12)
C18A	0.0593 (18)	0.0695 (17)	0.0786 (18)	−0.0120 (13)	0.0294 (15)	0.0049 (13)
C19A	0.0488 (14)	0.0555 (14)	0.0430 (13)	−0.0156 (11)	0.0198 (11)	−0.0067 (11)
C20A	0.0604 (17)	0.0611 (16)	0.0510 (14)	−0.0033 (12)	0.0207 (12)	0.0011 (12)
C21A	0.070 (2)	0.0701 (17)	0.0712 (18)	−0.0016 (13)	0.0336 (15)	−0.0112 (15)
C22A	0.0676 (19)	0.092 (2)	0.0433 (15)	−0.0150 (15)	0.0241 (14)	−0.0197 (14)
C23A	0.075 (2)	0.089 (2)	0.0415 (14)	−0.0057 (15)	0.0147 (13)	−0.0001 (13)
C24A	0.0673 (18)	0.0616 (15)	0.0463 (14)	−0.0017 (12)	0.0208 (12)	0.0021 (12)
C25A	0.105 (3)	0.142 (3)	0.067 (2)	−0.016 (2)	0.0017 (19)	0.028 (2)
F1B	0.1103 (14)	0.1356 (15)	0.0318 (8)	0.0088 (10)	0.0137 (8)	−0.0114 (8)
O1B	0.1111 (17)	0.1052 (15)	0.0386 (10)	−0.0094 (12)	0.0237 (10)	0.0162 (10)
O2B	0.144 (2)	0.0862 (13)	0.0374 (10)	−0.0312 (12)	0.0164 (11)	−0.0117 (9)
C1B	0.0719 (19)	0.0762 (18)	0.0438 (14)	0.0047 (14)	0.0235 (13)	0.0115 (13)
C2B	0.092 (2)	0.0739 (18)	0.0566 (16)	−0.0041 (15)	0.0296 (15)	0.0171 (14)
C3B	0.078 (2)	0.0675 (17)	0.0534 (15)	−0.0088 (14)	0.0246 (14)	0.0093 (12)
C4B	0.0757 (19)	0.0657 (16)	0.0450 (14)	−0.0076 (13)	0.0229 (13)	0.0012 (12)
C5B	0.0747 (18)	0.0518 (14)	0.0410 (13)	−0.0033 (12)	0.0190 (12)	−0.0021 (11)
C6B	0.091 (2)	0.0393 (12)	0.0399 (12)	0.0007 (12)	0.0181 (13)	−0.0006 (10)
C7B	0.090 (2)	0.0517 (14)	0.0502 (15)	−0.0103 (13)	0.0148 (14)	−0.0018 (12)
C8B	0.094 (2)	0.0509 (14)	0.0365 (13)	0.0011 (13)	0.0106 (13)	−0.0034 (11)
C9B	0.0791 (19)	0.0675 (16)	0.0326 (12)	0.0049 (13)	0.0205 (12)	−0.0020 (11)
N10B	0.0597 (13)	0.0527 (11)	0.0295 (9)	−0.0005 (9)	0.0149 (9)	0.0008 (8)
C11B	0.0604 (16)	0.0431 (12)	0.0352 (11)	0.0092 (10)	0.0173 (11)	−0.0004 (9)
C12B	0.0720 (17)	0.0487 (13)	0.0334 (12)	0.0074 (11)	0.0163 (11)	−0.0011 (10)
C13B	0.0636 (17)	0.0578 (14)	0.0376 (12)	0.0067 (11)	0.0205 (11)	0.0050 (10)
C14B	0.0534 (15)	0.0531 (13)	0.0380 (12)	0.0053 (10)	0.0184 (11)	0.0037 (10)
C18B	0.133 (3)	0.0632 (17)	0.0612 (17)	−0.0259 (16)	0.0363 (18)	−0.0025 (13)
C17B	0.130 (3)	0.0608 (18)	0.098 (2)	0.0314 (17)	0.036 (2)	0.0069 (16)
C16B	0.122 (3)	0.085 (2)	0.076 (2)	−0.0336 (18)	0.0287 (19)	0.0098 (16)
C15B	0.072 (2)	0.115 (2)	0.098 (2)	−0.0006 (18)	0.0368 (19)	0.0146 (19)
C19B	0.0498 (14)	0.0487 (12)	0.0312 (11)	0.0006 (10)	0.0120 (10)	−0.0019 (9)
C20B	0.0589 (17)	0.0733 (16)	0.0422 (13)	0.0160 (12)	0.0177 (12)	−0.0002 (12)
C21B	0.0594 (17)	0.0784 (17)	0.0414 (13)	0.0129 (13)	0.0084 (12)	0.0072 (12)
C22B	0.0685 (18)	0.0746 (16)	0.0287 (12)	−0.0044 (13)	0.0133 (12)	−0.0066 (11)
C23B	0.0670 (18)	0.0733 (17)	0.0449 (14)	0.0083 (13)	0.0219 (13)	−0.0144 (12)
C24B	0.0575 (16)	0.0590 (14)	0.0410 (13)	0.0105 (11)	0.0139 (11)	−0.0033 (11)
C25B	0.119 (3)	0.103 (2)	0.079 (2)	0.0127 (19)	0.055 (2)	−0.0173 (17)

Geometric parameters (Å, º)

F1A—C22A	1.359 (3)	F1B—C22B	1.353 (2)
O1A—C1A	1.216 (3)	O1B—C1B	1.227 (3)
O2A—C8A	1.232 (3)	O2B—C8B	1.239 (2)
C1A—C13A	1.462 (4)	C1B—C13B	1.464 (3)
C1A—C2A	1.517 (4)	C1B—C2B	1.504 (4)
C2A—C3A	1.475 (4)	C2B—C3B	1.530 (3)
C2A—H2A1	0.9700	C2B—H2B1	0.9700
C2A—H2A2	0.9700	C2B—H2B2	0.9700
C3A—C4A	1.496 (4)	C3B—C15B	1.526 (4)
C3A—C16A	1.499 (4)	C3B—C4B	1.533 (3)
C3A—C15A	1.615 (6)	C3B—C16B	1.534 (4)
C4A—C14A	1.504 (3)	C4B—C14B	1.504 (3)
C4A—H4A1	0.9700	C4B—H4B1	0.9700
C4A—H4A2	0.9700	C4B—H4B2	0.9700
C5A—C11A	1.494 (3)	C5B—C11B	1.504 (3)
C5A—C6A	1.533 (3)	C5B—C6B	1.529 (3)
C5A—H5A1	0.9700	C5B—H5B1	0.9700
C5A—H5A2	0.9700	C5B—H5B2	0.9700
C6A—C17A	1.521 (3)	C6B—C7B	1.515 (3)
C6A—C7A	1.529 (3)	C6B—C17B	1.527 (4)
C6A—C18A	1.533 (3)	C6B—C18B	1.530 (3)
C7A—C8A	1.498 (4)	C7B—C8B	1.497 (3)
C7A—H7A1	0.9700	C7B—H7B1	0.9700
C7A—H7A2	0.9700	C7B—H7B2	0.9700
C8A—C12A	1.456 (3)	C8B—C12B	1.453 (3)
C9A—C13A	1.495 (3)	C9B—C13B	1.493 (3)
C9A—C12A	1.508 (3)	C9B—C12B	1.511 (3)
C9A—C25A	1.529 (4)	C9B—C25B	1.524 (4)
C9A—H9A	0.9800	C9B—H9B	0.9800
N10A—C11A	1.401 (3)	N10B—C11B	1.399 (3)
N10A—C14A	1.401 (3)	N10B—C14B	1.402 (2)
N10A—C19A	1.449 (3)	N10B—C19B	1.453 (2)
C11A—C12A	1.348 (3)	C11B—C12B	1.346 (3)
C13A—C14A	1.347 (3)	C13B—C14B	1.349 (3)
C15A—H15A	0.9600	C18B—H18D	0.9600
C15A—H15B	0.9600	C18B—H18E	0.9600
C15A—H15C	0.9600	C18B—H18F	0.9600
C16A—H16A	0.9600	C17B—H17D	0.9600
C16A—H16B	0.9600	C17B—H17E	0.9600
C16A—H16C	0.9600	C17B—H17F	0.9600
C17A—H17A	0.9600	C16B—H16D	0.9600
C17A—H17B	0.9600	C16B—H16E	0.9600
C17A—H17C	0.9600	C16B—H16F	0.9600
C18A—H18A	0.9600	C15B—H15D	0.9600
C18A—H18B	0.9600	C15B—H15E	0.9600
C18A—H18C	0.9600	C15B—H15F	0.9600
C19A—C24A	1.371 (3)	C19B—C24B	1.372 (3)
C19A—C20A	1.377 (3)	C19B—C20B	1.377 (3)
C20A—C21A	1.383 (3)	C20B—C21B	1.384 (3)
C20A—H20A	0.9300	C20B—H20B	0.9300
C21A—C22A	1.361 (4)	C21B—C22B	1.355 (3)
C21A—H21A	0.9300	C21B—H21B	0.9300
C22A—C23A	1.359 (4)	C22B—C23B	1.362 (3)
C23A—C24A	1.374 (3)	C23B—C24B	1.382 (3)
C23A—H23A	0.9300	C23B—H23B	0.9300
C24A—H24A	0.9300	C24B—H24B	0.9300
C25A—H25A	0.9600	C25B—H25D	0.9600
C25A—H25B	0.9600	C25B—H25E	0.9600
C25A—H25C	0.9600	C25B—H25F	0.9600
O1A—C1A—C13A	122.3 (3)	O1B—C1B—C13B	121.2 (2)
O1A—C1A—C2A	121.6 (3)	O1B—C1B—C2B	120.4 (2)
C13A—C1A—C2A	116.1 (2)	C13B—C1B—C2B	118.3 (2)
C3A—C2A—C1A	115.8 (3)	C1B—C2B—C3B	114.3 (2)
C3A—C2A—H2A1	108.3	C1B—C2B—H2B1	108.7
C1A—C2A—H2A1	108.3	C3B—C2B—H2B1	108.7
C3A—C2A—H2A2	108.3	C1B—C2B—H2B2	108.7
C1A—C2A—H2A2	108.3	C3B—C2B—H2B2	108.7
H2A1—C2A—H2A2	107.4	H2B1—C2B—H2B2	107.6
C2A—C3A—C4A	112.2 (3)	C15B—C3B—C2B	111.0 (2)
C2A—C3A—C16A	116.8 (3)	C15B—C3B—C4B	110.4 (2)
C4A—C3A—C16A	112.2 (2)	C2B—C3B—C4B	107.3 (2)
C2A—C3A—C15A	103.8 (3)	C15B—C3B—C16B	109.3 (3)
C4A—C3A—C15A	105.0 (3)	C2B—C3B—C16B	109.1 (2)
C16A—C3A—C15A	105.5 (3)	C4B—C3B—C16B	109.8 (2)
C3A—C4A—C14A	113.7 (2)	C14B—C4B—C3B	113.46 (19)
C3A—C4A—H4A1	108.8	C14B—C4B—H4B1	108.9
C14A—C4A—H4A1	108.8	C3B—C4B—H4B1	108.9
C3A—C4A—H4A2	108.8	C14B—C4B—H4B2	108.9
C14A—C4A—H4A2	108.8	C3B—C4B—H4B2	108.9
H4A1—C4A—H4A2	107.7	H4B1—C4B—H4B2	107.7
C11A—C5A—C6A	113.11 (18)	C11B—C5B—C6B	113.56 (17)
C11A—C5A—H5A1	109.0	C11B—C5B—H5B1	108.9
C6A—C5A—H5A1	109.0	C6B—C5B—H5B1	108.9
C11A—C5A—H5A2	109.0	C11B—C5B—H5B2	108.9
C6A—C5A—H5A2	109.0	C6B—C5B—H5B2	108.9
H5A1—C5A—H5A2	107.8	H5B1—C5B—H5B2	107.7
C17A—C6A—C7A	110.93 (19)	C7B—C6B—C17B	109.6 (2)
C17A—C6A—C18A	109.43 (19)	C7B—C6B—C5B	107.96 (18)
C7A—C6A—C18A	108.98 (19)	C17B—C6B—C5B	110.3 (2)
C17A—C6A—C5A	111.03 (19)	C7B—C6B—C18B	109.4 (2)
C7A—C6A—C5A	107.47 (17)	C17B—C6B—C18B	109.5 (2)
C18A—C6A—C5A	108.95 (18)	C5B—C6B—C18B	110.12 (18)
C8A—C7A—C6A	112.5 (2)	C8B—C7B—C6B	113.0 (2)
C8A—C7A—H7A1	109.1	C8B—C7B—H7B1	109.0
C6A—C7A—H7A1	109.1	C6B—C7B—H7B1	109.0
C8A—C7A—H7A2	109.1	C8B—C7B—H7B2	109.0
C6A—C7A—H7A2	109.1	C6B—C7B—H7B2	109.0
H7A1—C7A—H7A2	107.8	H7B1—C7B—H7B2	107.8
O2A—C8A—C12A	120.9 (3)	O2B—C8B—C12B	120.5 (2)
O2A—C8A—C7A	121.0 (2)	O2B—C8B—C7B	120.4 (2)
C12A—C8A—C7A	118.1 (2)	C12B—C8B—C7B	118.98 (19)
C13A—C9A—C12A	108.2 (2)	C13B—C9B—C12B	109.86 (17)
C13A—C9A—C25A	111.7 (3)	C13B—C9B—C25B	111.8 (2)
C12A—C9A—C25A	110.4 (2)	C12B—C9B—C25B	111.4 (2)
C13A—C9A—H9A	108.9	C13B—C9B—H9B	107.9
C12A—C9A—H9A	108.9	C12B—C9B—H9B	107.9
C25A—C9A—H9A	108.9	C25B—C9B—H9B	107.9
C11A—N10A—C14A	118.98 (18)	C11B—N10B—C14B	120.13 (16)
C11A—N10A—C19A	120.14 (17)	C11B—N10B—C19B	119.04 (17)
C14A—N10A—C19A	120.64 (17)	C14B—N10B—C19B	119.81 (17)
C12A—C11A—N10A	120.1 (2)	C12B—C11B—N10B	120.21 (19)
C12A—C11A—C5A	122.9 (2)	C12B—C11B—C5B	122.7 (2)
N10A—C11A—C5A	116.93 (18)	N10B—C11B—C5B	117.05 (17)
C11A—C12A—C8A	120.2 (2)	C11B—C12B—C8B	119.7 (2)
C11A—C12A—C9A	119.7 (2)	C11B—C12B—C9B	121.7 (2)
C8A—C12A—C9A	120.1 (2)	C8B—C12B—C9B	118.65 (19)
C14A—C13A—C1A	120.1 (2)	C14B—C13B—C1B	119.6 (2)
C14A—C13A—C9A	120.9 (2)	C14B—C13B—C9B	121.9 (2)
C1A—C13A—C9A	119.0 (2)	C1B—C13B—C9B	118.49 (19)
C13A—C14A—N10A	119.3 (2)	C13B—C14B—N10B	120.1 (2)
C13A—C14A—C4A	124.4 (2)	C13B—C14B—C4B	123.0 (2)
N10A—C14A—C4A	116.25 (19)	N10B—C14B—C4B	116.87 (17)
C3A—C15A—H15A	109.5	C6B—C18B—H18D	109.5
C3A—C15A—H15B	109.5	C6B—C18B—H18E	109.5
H15A—C15A—H15B	109.5	H18D—C18B—H18E	109.5
C3A—C15A—H15C	109.5	C6B—C18B—H18F	109.5
H15A—C15A—H15C	109.5	H18D—C18B—H18F	109.5
H15B—C15A—H15C	109.5	H18E—C18B—H18F	109.5
C3A—C16A—H16A	109.5	C6B—C17B—H17D	109.5
C3A—C16A—H16B	109.5	C6B—C17B—H17E	109.5
H16A—C16A—H16B	109.5	H17D—C17B—H17E	109.5
C3A—C16A—H16C	109.5	C6B—C17B—H17F	109.5
H16A—C16A—H16C	109.5	H17D—C17B—H17F	109.5
H16B—C16A—H16C	109.5	H17E—C17B—H17F	109.5
C6A—C17A—H17A	109.5	C3B—C16B—H16D	109.5
C6A—C17A—H17B	109.5	C3B—C16B—H16E	109.5
H17A—C17A—H17B	109.5	H16D—C16B—H16E	109.5
C6A—C17A—H17C	109.5	C3B—C16B—H16F	109.5
H17A—C17A—H17C	109.5	H16D—C16B—H16F	109.5
H17B—C17A—H17C	109.5	H16E—C16B—H16F	109.5
C6A—C18A—H18A	109.5	C3B—C15B—H15D	109.5
C6A—C18A—H18B	109.5	C3B—C15B—H15E	109.5
H18A—C18A—H18B	109.5	H15D—C15B—H15E	109.5
C6A—C18A—H18C	109.5	C3B—C15B—H15F	109.5
H18A—C18A—H18C	109.5	H15D—C15B—H15F	109.5
H18B—C18A—H18C	109.5	H15E—C15B—H15F	109.5
C24A—C19A—C20A	120.4 (2)	C24B—C19B—C20B	120.13 (19)
C24A—C19A—N10A	121.1 (2)	C24B—C19B—N10B	120.26 (19)
C20A—C19A—N10A	118.5 (2)	C20B—C19B—N10B	119.60 (19)
C19A—C20A—C21A	119.6 (2)	C19B—C20B—C21B	120.8 (2)
C19A—C20A—H20A	120.2	C19B—C20B—H20B	119.6
C21A—C20A—H20A	120.2	C21B—C20B—H20B	119.6
C22A—C21A—C20A	118.5 (2)	C22B—C21B—C20B	117.8 (2)
C22A—C21A—H21A	120.8	C22B—C21B—H21B	121.1
C20A—C21A—H21A	120.8	C20B—C21B—H21B	121.1
F1A—C22A—C23A	119.5 (3)	F1B—C22B—C21B	118.4 (2)
F1A—C22A—C21A	117.7 (3)	F1B—C22B—C23B	118.8 (2)
C23A—C22A—C21A	122.8 (2)	C21B—C22B—C23B	122.8 (2)
C22A—C23A—C24A	118.6 (2)	C22B—C23B—C24B	119.3 (2)
C22A—C23A—H23A	120.7	C22B—C23B—H23B	120.4
C24A—C23A—H23A	120.7	C24B—C23B—H23B	120.4
C19A—C24A—C23A	120.1 (2)	C19B—C24B—C23B	119.3 (2)
C19A—C24A—H24A	119.9	C19B—C24B—H24B	120.4
C23A—C24A—H24A	119.9	C23B—C24B—H24B	120.4
C9A—C25A—H25A	109.5	C9B—C25B—H25D	109.5
C9A—C25A—H25B	109.5	C9B—C25B—H25E	109.5
H25A—C25A—H25B	109.5	H25D—C25B—H25E	109.5
C9A—C25A—H25C	109.5	C9B—C25B—H25F	109.5
H25A—C25A—H25C	109.5	H25D—C25B—H25F	109.5
H25B—C25A—H25C	109.5	H25E—C25B—H25F	109.5
O1A—C1A—C2A—C3A	−148.3 (4)	O1B—C1B—C2B—C3B	154.3 (2)
C13A—C1A—C2A—C3A	30.8 (5)	C13B—C1B—C2B—C3B	−27.8 (3)
C1A—C2A—C3A—C4A	−49.5 (5)	C1B—C2B—C3B—C15B	−67.5 (3)
C1A—C2A—C3A—C16A	179.0 (3)	C1B—C2B—C3B—C4B	53.2 (3)
C1A—C2A—C3A—C15A	63.4 (4)	C1B—C2B—C3B—C16B	172.1 (2)
C2A—C3A—C4A—C14A	39.4 (4)	C15B—C3B—C4B—C14B	71.2 (3)
C16A—C3A—C4A—C14A	173.2 (3)	C2B—C3B—C4B—C14B	−49.9 (3)
C15A—C3A—C4A—C14A	−72.7 (3)	C16B—C3B—C4B—C14B	−168.3 (2)
C11A—C5A—C6A—C17A	71.5 (2)	C11B—C5B—C6B—C7B	49.1 (3)
C11A—C5A—C6A—C7A	−50.0 (3)	C11B—C5B—C6B—C17B	−70.6 (3)
C11A—C5A—C6A—C18A	−167.92 (19)	C11B—C5B—C6B—C18B	168.5 (2)
C17A—C6A—C7A—C8A	−65.3 (3)	C17B—C6B—C7B—C8B	65.7 (3)
C18A—C6A—C7A—C8A	174.19 (19)	C5B—C6B—C7B—C8B	−54.4 (3)
C5A—C6A—C7A—C8A	56.3 (3)	C18B—C6B—C7B—C8B	−174.2 (2)
C6A—C7A—C8A—O2A	147.7 (2)	C6B—C7B—C8B—O2B	−150.6 (2)
C6A—C7A—C8A—C12A	−33.5 (3)	C6B—C7B—C8B—C12B	32.3 (3)
C14A—N10A—C11A—C12A	17.3 (3)	C14B—N10B—C11B—C12B	−11.6 (3)
C19A—N10A—C11A—C12A	−168.4 (2)	C19B—N10B—C11B—C12B	−179.98 (19)
C14A—N10A—C11A—C5A	−159.9 (2)	C14B—N10B—C11B—C5B	165.59 (19)
C19A—N10A—C11A—C5A	14.4 (3)	C19B—N10B—C11B—C5B	−2.8 (3)
C6A—C5A—C11A—C12A	21.0 (3)	C6B—C5B—C11B—C12B	−21.4 (3)
C6A—C5A—C11A—N10A	−161.89 (19)	C6B—C5B—C11B—N10B	161.5 (2)
N10A—C11A—C12A—C8A	−172.0 (2)	N10B—C11B—C12B—C8B	173.1 (2)
C5A—C11A—C12A—C8A	5.0 (4)	C5B—C11B—C12B—C8B	−3.9 (3)
N10A—C11A—C12A—C9A	11.3 (3)	N10B—C11B—C12B—C9B	−7.4 (3)
C5A—C11A—C12A—C9A	−171.7 (2)	C5B—C11B—C12B—C9B	175.6 (2)
O2A—C8A—C12A—C11A	−179.7 (2)	O2B—C8B—C12B—C11B	−178.6 (2)
C7A—C8A—C12A—C11A	1.5 (3)	C7B—C8B—C12B—C11B	−1.6 (3)
O2A—C8A—C12A—C9A	−3.1 (4)	O2B—C8B—C12B—C9B	1.8 (4)
C7A—C8A—C12A—C9A	178.1 (2)	C7B—C8B—C12B—C9B	178.9 (2)
C13A—C9A—C12A—C11A	−35.1 (3)	C13B—C9B—C12B—C11B	24.4 (3)
C25A—C9A—C12A—C11A	87.3 (3)	C25B—C9B—C12B—C11B	−100.0 (3)
C13A—C9A—C12A—C8A	148.2 (2)	C13B—C9B—C12B—C8B	−156.1 (2)
C25A—C9A—C12A—C8A	−89.3 (3)	C25B—C9B—C12B—C8B	79.5 (3)
O1A—C1A—C13A—C14A	177.5 (3)	O1B—C1B—C13B—C14B	173.6 (2)
C2A—C1A—C13A—C14A	−1.6 (5)	C2B—C1B—C13B—C14B	−4.3 (4)
O1A—C1A—C13A—C9A	0.0 (5)	O1B—C1B—C13B—C9B	−7.1 (4)
C2A—C1A—C13A—C9A	−179.1 (3)	C2B—C1B—C13B—C9B	175.0 (2)
C12A—C9A—C13A—C14A	34.8 (4)	C12B—C9B—C13B—C14B	−25.6 (3)
C25A—C9A—C13A—C14A	−86.9 (3)	C25B—C9B—C13B—C14B	98.6 (3)
C12A—C9A—C13A—C1A	−147.8 (3)	C12B—C9B—C13B—C1B	155.1 (2)
C25A—C9A—C13A—C1A	90.6 (3)	C25B—C9B—C13B—C1B	−80.7 (3)
C1A—C13A—C14A—N10A	172.3 (3)	C1B—C13B—C14B—N10B	−171.0 (2)
C9A—C13A—C14A—N10A	−10.2 (4)	C9B—C13B—C14B—N10B	9.7 (3)
C1A—C13A—C14A—C4A	−7.6 (5)	C1B—C13B—C14B—C4B	7.4 (4)
C9A—C13A—C14A—C4A	169.8 (3)	C9B—C13B—C14B—C4B	−171.9 (2)
C11A—N10A—C14A—C13A	−18.0 (4)	C11B—N10B—C14B—C13B	10.5 (3)
C19A—N10A—C14A—C13A	167.7 (2)	C19B—N10B—C14B—C13B	178.8 (2)
C11A—N10A—C14A—C4A	162.0 (2)	C11B—N10B—C14B—C4B	−167.9 (2)
C19A—N10A—C14A—C4A	−12.3 (3)	C19B—N10B—C14B—C4B	0.4 (3)
C3A—C4A—C14A—C13A	−11.9 (5)	C3B—C4B—C14B—C13B	21.6 (3)
C3A—C4A—C14A—N10A	168.1 (3)	C3B—C4B—C14B—N10B	−160.0 (2)
C11A—N10A—C19A—C24A	−89.3 (3)	C11B—N10B—C19B—C24B	86.5 (3)
C14A—N10A—C19A—C24A	85.0 (3)	C14B—N10B—C19B—C24B	−81.9 (3)
C11A—N10A—C19A—C20A	90.3 (3)	C11B—N10B—C19B—C20B	−92.8 (3)
C14A—N10A—C19A—C20A	−95.5 (3)	C14B—N10B—C19B—C20B	98.7 (2)
C24A—C19A—C20A—C21A	−0.2 (4)	C24B—C19B—C20B—C21B	−0.1 (4)
N10A—C19A—C20A—C21A	−179.8 (2)	N10B—C19B—C20B—C21B	179.3 (2)
C19A—C20A—C21A—C22A	−0.3 (4)	C19B—C20B—C21B—C22B	0.2 (4)
C20A—C21A—C22A—F1A	−179.0 (2)	C20B—C21B—C22B—F1B	−179.2 (2)
C20A—C21A—C22A—C23A	0.6 (4)	C20B—C21B—C22B—C23B	−0.4 (4)
F1A—C22A—C23A—C24A	179.3 (2)	F1B—C22B—C23B—C24B	179.4 (2)
C21A—C22A—C23A—C24A	−0.3 (4)	C21B—C22B—C23B—C24B	0.6 (4)
C20A—C19A—C24A—C23A	0.5 (4)	C20B—C19B—C24B—C23B	0.3 (3)
N10A—C19A—C24A—C23A	−179.9 (2)	N10B—C19B—C24B—C23B	−179.1 (2)
C22A—C23A—C24A—C19A	−0.3 (4)	C22B—C23B—C24B—C19B	−0.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9A—H9A···O1A	0.98	2.51	2.850 (4)	100
C9A—H9A···O2A	0.98	2.52	2.856 (5)	100
C9B—H9B···O1B	0.98	2.51	2.828 (4)	98
C9B—H9B···O2B	0.98	2.53	2.819 (3)	97
C24A—H24A···O2A^i	0.93	2.50	3.247 (3)	138

Symmetry code: (i) x, −y+1/2, z+1/2.

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

Crystal data

C26H32FNO2	F(000) = 1760
Mr = 409.53	Dx = 1.184 Mg m^−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54180 Å
a = 27.454 (1) Å	Cell parameters from 25 reflections
b = 12.2738 (10) Å	θ = 12.5–18.0°
c = 16.2792 (10) Å	µ = 0.63 mm^−1
β = 123.118 (10)°	T = 293 K
V = 4594.4 (5) Å^3	Block, pale yellow
Z = 8	0.20 × 0.18 × 0.16 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.053
Radiation source: fine-focus sealed tube	θmax = 72.7°, θmin = 3.9°
Graphite monochromator	h = 0→34
ω/2θ scans	k = 0→15
4454 measured reflections	l = −20→16
4374 independent reflections	3 standard reflections every 200 reflections
3087 reflections with I > 2σ(I)	intensity decay: <1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.196	w = 1/[σ^2(Fo^2) + (0.0504P)^2 + 0.0465P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
4374 reflections	Δρmax = 0.17 e Å^−3
272 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00046 (13)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F1	0.00474 (8)	0.66354 (13)	0.14003 (19)	0.1566 (9)
O1	0.23797 (7)	0.02710 (13)	0.51580 (11)	0.0882 (5)
O2	0.25392 (7)	0.03973 (14)	0.23311 (11)	0.0843 (5)
C1	0.20570 (8)	0.10666 (16)	0.48565 (14)	0.0621 (5)
C2	0.19344 (9)	0.16913 (17)	0.55147 (14)	0.0658 (5)
H2A	0.2241	0.2223	0.5880	0.079*
H2B	0.1942	0.1193	0.5984	0.079*
C3	0.13527 (9)	0.22761 (16)	0.49688 (14)	0.0627 (5)
C4	0.13309 (9)	0.29930 (15)	0.41763 (14)	0.0613 (5)
H4A	0.0939	0.3273	0.3750	0.074*
H4B	0.1589	0.3610	0.4490	0.074*
C5	0.15461 (9)	0.32023 (15)	0.13792 (14)	0.0628 (5)
H5A	0.1801	0.3828	0.1673	0.075*
H5B	0.1150	0.3470	0.0981	0.075*
C6	0.16966 (9)	0.26095 (16)	0.07125 (14)	0.0637 (5)
C7	0.22652 (9)	0.20004 (19)	0.13549 (15)	0.0705 (5)
H7A	0.2350	0.1587	0.0940	0.085*
H7B	0.2576	0.2524	0.1720	0.085*
C8	0.22509 (8)	0.12410 (16)	0.20596 (14)	0.0624 (5)
C9	0.19083 (8)	0.08003 (14)	0.31875 (14)	0.0598 (5)
H9	0.2299	0.0485	0.3587	0.072*
N10	0.13451 (7)	0.28682 (11)	0.26690 (11)	0.0546 (4)
C11	0.16033 (7)	0.24963 (14)	0.21787 (12)	0.0533 (4)
C12	0.19015 (8)	0.15430 (14)	0.24492 (12)	0.0549 (4)
C13	0.18043 (8)	0.14522 (14)	0.38568 (13)	0.0549 (4)
C14	0.15026 (7)	0.23991 (14)	0.35640 (13)	0.0531 (4)
C15	0.08592 (10)	0.14393 (19)	0.45133 (18)	0.0790 (6)
H15A	0.0894	0.0980	0.4070	0.118*
H15B	0.0492	0.1811	0.4162	0.118*
H15C	0.0882	0.1002	0.5022	0.118*
C16	0.12988 (12)	0.3003 (2)	0.56749 (18)	0.0864 (7)
H16A	0.0929	0.3366	0.5327	0.130*
H16B	0.1605	0.3536	0.5953	0.130*
H16C	0.1329	0.2566	0.6190	0.130*
C17	0.12170 (10)	0.18051 (19)	0.00377 (15)	0.0780 (6)
H17A	0.1319	0.1444	−0.0371	0.117*
H17B	0.0858	0.2191	−0.0366	0.117*
H17C	0.1173	0.1275	0.0426	0.117*
C18	0.17534 (14)	0.3461 (2)	0.00786 (19)	0.0927 (8)
H18A	0.2052	0.3974	0.0495	0.139*
H18B	0.1390	0.3837	−0.0321	0.139*
H18C	0.1853	0.3104	−0.0335	0.139*
C19	0.10109 (8)	0.38656 (14)	0.23467 (13)	0.0546 (4)
C20	0.04193 (9)	0.38052 (17)	0.16834 (19)	0.0833 (7)
H20	0.0240	0.3132	0.1451	0.100*
C21	0.00942 (10)	0.4745 (2)	0.1365 (3)	0.1083 (10)
H21	−0.0306	0.4718	0.0917	0.130*
C22	0.03712 (11)	0.57131 (18)	0.1719 (2)	0.0931 (8)
C23	0.09522 (10)	0.57980 (15)	0.23732 (17)	0.0732 (6)
H23	0.1127	0.6476	0.2600	0.088*
C24	0.12802 (8)	0.48571 (14)	0.26964 (14)	0.0600 (5)
H24	0.1680	0.4893	0.3147	0.072*
C25	0.14722 (11)	−0.01493 (16)	0.27060 (18)	0.0757 (6)
H25A	0.1576	−0.0578	0.2323	0.091*
H25B	0.1512	−0.0616	0.3221	0.091*
C26	0.08473 (11)	0.01783 (19)	0.2055 (2)	0.0889 (7)
H26A	0.0797	0.0587	0.1503	0.107*
H26B	0.0749	0.0657	0.2418	0.107*
C27	0.04316 (16)	−0.0778 (3)	0.1670 (3)	0.1358 (13)
H27A	0.0040	−0.0516	0.1252	0.204*
H27B	0.0468	−0.1171	0.2210	0.204*
H27C	0.0522	−0.1251	0.1302	0.204*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.1171 (13)	0.0653 (10)	0.229 (2)	0.0436 (9)	0.0566 (14)	0.0379 (12)
O1	0.1021 (11)	0.0873 (11)	0.0796 (10)	0.0452 (9)	0.0524 (9)	0.0350 (9)
O2	0.0903 (10)	0.0870 (11)	0.0814 (10)	0.0338 (9)	0.0507 (8)	0.0091 (8)
C1	0.0611 (10)	0.0588 (10)	0.0640 (11)	0.0100 (8)	0.0326 (9)	0.0141 (9)
C2	0.0725 (11)	0.0663 (12)	0.0574 (10)	0.0040 (9)	0.0348 (9)	0.0078 (9)
C3	0.0753 (12)	0.0569 (10)	0.0652 (11)	0.0039 (9)	0.0443 (10)	0.0044 (9)
C4	0.0748 (11)	0.0481 (9)	0.0658 (11)	0.0064 (8)	0.0415 (10)	0.0033 (8)
C5	0.0821 (12)	0.0466 (9)	0.0607 (10)	−0.0030 (9)	0.0397 (9)	0.0020 (8)
C6	0.0796 (12)	0.0560 (10)	0.0552 (10)	−0.0081 (9)	0.0365 (9)	−0.0017 (8)
C7	0.0732 (12)	0.0778 (14)	0.0679 (12)	−0.0054 (10)	0.0432 (10)	−0.0060 (10)
C8	0.0605 (10)	0.0637 (11)	0.0578 (10)	0.0033 (9)	0.0289 (8)	−0.0047 (9)
C9	0.0671 (10)	0.0493 (9)	0.0652 (11)	0.0146 (8)	0.0375 (9)	0.0095 (8)
N10	0.0669 (8)	0.0413 (7)	0.0582 (8)	0.0097 (6)	0.0359 (7)	0.0076 (6)
C11	0.0582 (9)	0.0447 (8)	0.0535 (9)	−0.0025 (7)	0.0282 (8)	−0.0024 (7)
C12	0.0594 (9)	0.0483 (9)	0.0547 (9)	0.0030 (7)	0.0296 (8)	0.0001 (7)
C13	0.0592 (9)	0.0471 (9)	0.0585 (10)	0.0074 (7)	0.0322 (8)	0.0067 (7)
C14	0.0578 (9)	0.0448 (8)	0.0562 (9)	0.0024 (7)	0.0307 (8)	0.0054 (7)
C15	0.0758 (13)	0.0759 (14)	0.0966 (16)	0.0005 (11)	0.0543 (12)	0.0088 (12)
C16	0.1130 (18)	0.0837 (16)	0.0808 (15)	0.0173 (14)	0.0645 (14)	0.0047 (12)
C17	0.0829 (13)	0.0711 (13)	0.0606 (11)	−0.0057 (11)	0.0269 (10)	−0.0089 (10)
C18	0.133 (2)	0.0789 (16)	0.0850 (15)	−0.0073 (15)	0.0719 (16)	0.0074 (13)
C19	0.0603 (9)	0.0414 (9)	0.0598 (9)	0.0047 (7)	0.0313 (8)	0.0068 (7)
C20	0.0619 (11)	0.0513 (11)	0.1052 (16)	−0.0032 (9)	0.0253 (11)	0.0030 (11)
C21	0.0601 (12)	0.0714 (15)	0.143 (2)	0.0112 (11)	0.0227 (14)	0.0191 (16)
C22	0.0816 (15)	0.0511 (12)	0.125 (2)	0.0230 (11)	0.0423 (15)	0.0244 (13)
C23	0.0885 (14)	0.0399 (9)	0.0858 (14)	0.0019 (9)	0.0441 (12)	0.0048 (9)
C24	0.0631 (10)	0.0472 (9)	0.0636 (10)	0.0010 (8)	0.0307 (8)	0.0022 (8)
C25	0.1057 (16)	0.0433 (10)	0.0900 (15)	0.0019 (10)	0.0611 (14)	0.0009 (10)
C26	0.0950 (17)	0.0615 (13)	0.1085 (19)	−0.0149 (12)	0.0544 (15)	−0.0122 (13)
C27	0.130 (3)	0.096 (2)	0.196 (4)	−0.046 (2)	0.099 (3)	−0.048 (2)

Geometric parameters (Å, º)

F1—C22	1.355 (2)	C13—C14	1.354 (2)
O1—C1	1.227 (2)	C15—H15A	0.9600
O2—C8	1.230 (2)	C15—H15B	0.9600
C1—C13	1.456 (2)	C15—H15C	0.9600
C1—C2	1.498 (3)	C16—H16A	0.9600
C2—C3	1.518 (3)	C16—H16B	0.9600
C2—H2A	0.9700	C16—H16C	0.9600
C2—H2B	0.9700	C17—H17A	0.9600
C3—C16	1.525 (3)	C17—H17B	0.9600
C3—C15	1.530 (3)	C17—H17C	0.9600
C3—C4	1.536 (2)	C18—H18A	0.9600
C4—C14	1.503 (2)	C18—H18B	0.9600
C4—H4A	0.9700	C18—H18C	0.9600
C4—H4B	0.9700	C19—C24	1.375 (2)
C5—C11	1.499 (2)	C19—C20	1.376 (3)
C5—C6	1.539 (3)	C20—C21	1.375 (3)
C5—H5A	0.9700	C20—H20	0.9300
C5—H5B	0.9700	C21—C22	1.358 (3)
C6—C7	1.519 (3)	C21—H21	0.9300
C6—C17	1.528 (3)	C22—C23	1.354 (3)
C6—C18	1.536 (3)	C23—C24	1.380 (3)
C7—C8	1.496 (3)	C23—H23	0.9300
C7—H7A	0.9700	C24—H24	0.9300
C7—H7B	0.9700	C25—C26	1.497 (3)
C8—C12	1.457 (3)	C25—H25A	0.9700
C9—C13	1.499 (2)	C25—H25B	0.9700
C9—C12	1.501 (2)	C26—C27	1.513 (3)
C9—C25	1.543 (3)	C26—H26A	0.9700
C9—H9	0.9800	C26—H26B	0.9700
N10—C14	1.398 (2)	C27—H27A	0.9600
N10—C11	1.402 (2)	C27—H27B	0.9600
N10—C19	1.446 (2)	C27—H27C	0.9600
C11—C12	1.356 (2)
O1—C1—C13	120.36 (18)	N10—C14—C4	117.45 (14)
O1—C1—C2	121.10 (17)	C3—C15—H15A	109.5
C13—C1—C2	118.48 (16)	C3—C15—H15B	109.5
C1—C2—C3	113.51 (16)	H15A—C15—H15B	109.5
C1—C2—H2A	108.9	C3—C15—H15C	109.5
C3—C2—H2A	108.9	H15A—C15—H15C	109.5
C1—C2—H2B	108.9	H15B—C15—H15C	109.5
C3—C2—H2B	108.9	C3—C16—H16A	109.5
H2A—C2—H2B	107.7	C3—C16—H16B	109.5
C2—C3—C16	109.85 (18)	H16A—C16—H16B	109.5
C2—C3—C15	109.63 (17)	C3—C16—H16C	109.5
C16—C3—C15	109.45 (17)	H16A—C16—H16C	109.5
C2—C3—C4	107.98 (15)	H16B—C16—H16C	109.5
C16—C3—C4	108.82 (16)	C6—C17—H17A	109.5
C15—C3—C4	111.09 (17)	C6—C17—H17B	109.5
C14—C4—C3	113.38 (15)	H17A—C17—H17B	109.5
C14—C4—H4A	108.9	C6—C17—H17C	109.5
C3—C4—H4A	108.9	H17A—C17—H17C	109.5
C14—C4—H4B	108.9	H17B—C17—H17C	109.5
C3—C4—H4B	108.9	C6—C18—H18A	109.5
H4A—C4—H4B	107.7	C6—C18—H18B	109.5
C11—C5—C6	113.45 (15)	H18A—C18—H18B	109.5
C11—C5—H5A	108.9	C6—C18—H18C	109.5
C6—C5—H5A	108.9	H18A—C18—H18C	109.5
C11—C5—H5B	108.9	H18B—C18—H18C	109.5
C6—C5—H5B	108.9	C24—C19—C20	120.62 (17)
H5A—C5—H5B	107.7	C24—C19—N10	120.53 (16)
C7—C6—C17	109.57 (17)	C20—C19—N10	118.84 (16)
C7—C6—C18	110.77 (19)	C21—C20—C19	119.7 (2)
C17—C6—C18	108.70 (18)	C21—C20—H20	120.1
C7—C6—C5	108.55 (15)	C19—C20—H20	120.1
C17—C6—C5	110.75 (17)	C22—C21—C20	118.4 (2)
C18—C6—C5	108.49 (17)	C22—C21—H21	120.8
C8—C7—C6	112.80 (16)	C20—C21—H21	120.8
C8—C7—H7A	109.0	C23—C22—F1	118.8 (2)
C6—C7—H7A	109.0	C23—C22—C21	123.2 (2)
C8—C7—H7B	109.0	F1—C22—C21	118.1 (2)
C6—C7—H7B	109.0	C22—C23—C24	118.61 (19)
H7A—C7—H7B	107.8	C22—C23—H23	120.7
O2—C8—C12	120.33 (18)	C24—C23—H23	120.7
O2—C8—C7	121.29 (18)	C19—C24—C23	119.44 (18)
C12—C8—C7	118.34 (17)	C19—C24—H24	120.3
C13—C9—C12	109.51 (14)	C23—C24—H24	120.3
C13—C9—C25	111.65 (16)	C26—C25—C9	115.32 (17)
C12—C9—C25	112.68 (16)	C26—C25—H25A	108.4
C13—C9—H9	107.6	C9—C25—H25A	108.4
C12—C9—H9	107.6	C26—C25—H25B	108.4
C25—C9—H9	107.6	C9—C25—H25B	108.4
C14—N10—C11	119.65 (14)	H25A—C25—H25B	107.5
C14—N10—C19	120.07 (14)	C25—C26—C27	113.5 (2)
C11—N10—C19	119.14 (14)	C25—C26—H26A	108.9
C12—C11—N10	119.94 (16)	C27—C26—H26A	108.9
C12—C11—C5	122.63 (17)	C25—C26—H26B	108.9
N10—C11—C5	117.41 (15)	C27—C26—H26B	108.9
C11—C12—C8	120.14 (16)	H26A—C26—H26B	107.7
C11—C12—C9	121.70 (16)	C26—C27—H27A	109.5
C8—C12—C9	118.09 (15)	C26—C27—H27B	109.5
C14—C13—C1	119.95 (17)	H27A—C27—H27B	109.5
C14—C13—C9	121.65 (16)	C26—C27—H27C	109.5
C1—C13—C9	118.35 (15)	H27A—C27—H27C	109.5
C13—C14—N10	120.16 (16)	H27B—C27—H27C	109.5
C13—C14—C4	122.39 (16)
O1—C1—C2—C3	−153.64 (19)	C2—C1—C13—C14	4.8 (3)
C13—C1—C2—C3	29.0 (3)	O1—C1—C13—C9	5.0 (3)
C1—C2—C3—C16	−172.76 (17)	C2—C1—C13—C9	−177.60 (17)
C1—C2—C3—C15	66.9 (2)	C12—C9—C13—C14	26.8 (2)
C1—C2—C3—C4	−54.2 (2)	C25—C9—C13—C14	−98.7 (2)
C2—C3—C4—C14	48.9 (2)	C12—C9—C13—C1	−150.80 (16)
C16—C3—C4—C14	168.09 (17)	C25—C9—C13—C1	83.7 (2)
C15—C3—C4—C14	−71.4 (2)	C1—C13—C14—N10	169.03 (16)
C11—C5—C6—C7	−47.3 (2)	C9—C13—C14—N10	−8.5 (3)
C11—C5—C6—C17	73.1 (2)	C1—C13—C14—C4	−10.2 (3)
C11—C5—C6—C18	−167.72 (18)	C9—C13—C14—C4	172.34 (17)
C17—C6—C7—C8	−65.9 (2)	C11—N10—C14—C13	−13.8 (3)
C18—C6—C7—C8	174.17 (17)	C19—N10—C14—C13	178.52 (16)
C5—C6—C7—C8	55.2 (2)	C11—N10—C14—C4	165.39 (15)
C6—C7—C8—O2	149.49 (19)	C19—N10—C14—C4	−2.3 (2)
C6—C7—C8—C12	−32.7 (2)	C3—C4—C14—C13	−18.3 (3)
C14—N10—C11—C12	14.5 (3)	C3—C4—C14—N10	162.53 (16)
C19—N10—C11—C12	−177.74 (16)	C14—N10—C19—C24	81.4 (2)
C14—N10—C11—C5	−164.06 (16)	C11—N10—C19—C24	−86.3 (2)
C19—N10—C11—C5	3.7 (2)	C14—N10—C19—C20	−98.7 (2)
C6—C5—C11—C12	16.6 (3)	C11—N10—C19—C20	93.6 (2)
C6—C5—C11—N10	−164.88 (15)	C24—C19—C20—C21	0.2 (4)
N10—C11—C12—C8	−169.75 (16)	N10—C19—C20—C21	−179.7 (2)
C5—C11—C12—C8	8.7 (3)	C19—C20—C21—C22	0.1 (5)
N10—C11—C12—C9	7.1 (3)	C20—C21—C22—C23	−0.2 (5)
C5—C11—C12—C9	−174.39 (16)	C20—C21—C22—F1	179.9 (3)
O2—C8—C12—C11	177.26 (18)	F1—C22—C23—C24	180.0 (2)
C7—C8—C12—C11	−0.6 (3)	C21—C22—C23—C24	0.1 (4)
O2—C8—C12—C9	0.3 (3)	C20—C19—C24—C23	−0.3 (3)
C7—C8—C12—C9	−177.53 (16)	N10—C19—C24—C23	179.62 (17)
C13—C9—C12—C11	−26.0 (2)	C22—C23—C24—C19	0.2 (3)
C25—C9—C12—C11	98.9 (2)	C13—C9—C25—C26	62.7 (2)
C13—C9—C12—C8	150.88 (16)	C12—C9—C25—C26	−61.1 (2)
C25—C9—C12—C8	−84.2 (2)	C9—C25—C26—C27	−175.0 (2)
O1—C1—C13—C14	−172.58 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1	0.98	2.46	2.802 (2)	100
C9—H9···O2	0.98	2.47	2.798 (4)	99
C5—H5A···O2^i	0.97	2.53	3.494 (2)	171
C24—H24···O1^ii	0.93	2.56	3.423 (3)	155

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