9-(3-Fluoro-phen-yl)-3,3,6,6-tetra-methyl-1,2,3,4,5,6,7,8,9,10-deca-hydro-acridine-1,8-dione.

In the title mol-ecule, C23H26FNO2, the central ring of the acridinedione system adopts a slight boat conformation and the four essentially planar atoms of this ring [maximum deviation = 0.019 (1) Å] form a dihedral angle of 89.98 (6)° with the benzene ring. The two outer rings of the acridinedione system adopt sofa conformations. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules, forming chains along [001].

Related literature

For applications of acridines, see: Murugan et al. (1998 ▶); Leon et al. (2008 ▶). Josephrajan et al. (2005 ▶); Srividya et al. (1998 ▶, 1996 ▶). For related structures, see: Balamurugan et al. (2009 ▶); Zhao & Teng (2008 ▶); Kant et al. (2013 ▶). For ring conformations, see: Duax & Norton (1975 ▶).

Experimental

Crystal data

C23H26FNO2

M = 367.45

Monoclinic,

a = 11.0505 (3) Å

b = 12.8264 (3) Å

c = 13.8548 (3) Å

β = 100.215 (2)°

V = 1932.63 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.897, T max = 1.000

30330 measured reflections

3789 independent reflections

2922 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.118

S = 1.03

3789 reflections

248 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812050556/lh5569sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050556/lh5569Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812050556/lh5569Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H26FNO2	F(000) = 784
Mr = 367.45	Dx = 1.263 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11314 reflections
a = 11.0505 (3) Å	θ = 3.5–29.1°
b = 12.8264 (3) Å	µ = 0.09 mm−1
c = 13.8548 (3) Å	T = 293 K
β = 100.215 (2)°	Block, yellow
V = 1932.63 (8) Å3	0.3 × 0.2 × 0.2 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3789 independent reflections
Radiation source: fine-focus sealed tube	2922 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.5°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −15→15
Tmin = 0.897, Tmax = 1.000	l = −17→17
30330 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0534P)2 + 0.5565P] where P = (Fo2 + 2Fc2)/3
3789 reflections	(Δ/σ)max = 0.002
248 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

	x	y	z	Uiso*/Ueq
F1	0.41296 (13)	0.61151 (11)	0.95736 (11)	0.0872 (5)
O1	0.37340 (11)	0.15628 (10)	1.02926 (8)	0.0458 (3)
O2	−0.05752 (11)	0.26403 (9)	0.87999 (9)	0.0447 (3)
C1	0.40151 (14)	0.17311 (12)	0.94855 (10)	0.0314 (3)
C2	0.52391 (14)	0.13764 (13)	0.92694 (11)	0.0350 (4)
H2A	0.5477	0.0743	0.9637	0.042*
H2B	0.5849	0.1905	0.9503	0.042*
C3	0.52646 (14)	0.11663 (12)	0.81853 (11)	0.0326 (4)
C4	0.47300 (15)	0.21159 (14)	0.75919 (11)	0.0369 (4)
H4A	0.5312	0.2687	0.7715	0.044*
H4B	0.4616	0.1949	0.6899	0.044*
C4A	0.35251 (14)	0.24594 (11)	0.78386 (11)	0.0299 (3)
C5	0.06856 (15)	0.34840 (14)	0.62736 (11)	0.0374 (4)
H5A	0.0487	0.2898	0.5831	0.045*
H5B	0.1117	0.3997	0.5947	0.045*
C5A	0.15152 (14)	0.31198 (12)	0.71821 (11)	0.0300 (3)
C6	−0.05098 (15)	0.39660 (14)	0.64830 (12)	0.0382 (4)
C7	−0.10509 (15)	0.32075 (15)	0.71400 (13)	0.0436 (4)
H7A	−0.1781	0.3519	0.7317	0.052*
H7B	−0.1303	0.2579	0.6769	0.052*
C8	−0.01831 (15)	0.29119 (12)	0.80649 (12)	0.0333 (4)
C8A	0.11243 (14)	0.29285 (11)	0.80350 (11)	0.0299 (3)
C9	0.20404 (14)	0.27571 (12)	0.89720 (11)	0.0311 (3)
H9	0.1689	0.2262	0.9385	0.037*
C9A	0.32076 (14)	0.23003 (12)	0.87301 (11)	0.0304 (3)
N10	0.27307 (11)	0.29683 (10)	0.71127 (9)	0.0329 (3)
H10	0.2999	0.3196	0.6606	0.039*
C11	0.65972 (16)	0.09985 (16)	0.80536 (13)	0.0476 (5)
H11A	0.6623	0.0897	0.7371	0.071*
H11B	0.6926	0.0395	0.8418	0.071*
H11C	0.7079	0.1599	0.8290	0.071*
C12	0.45147 (17)	0.01935 (14)	0.78447 (14)	0.0487 (5)
H12A	0.3677	0.0297	0.7923	0.073*
H12B	0.4853	−0.0394	0.8230	0.073*
H12C	0.4543	0.0065	0.7166	0.073*
C13	−0.02574 (19)	0.50270 (14)	0.69808 (15)	0.0511 (5)
H13A	−0.1012	0.5313	0.7116	0.077*
H13B	0.0084	0.5490	0.6555	0.077*
H13C	0.0315	0.4944	0.7584	0.077*
C14	−0.14131 (19)	0.41061 (19)	0.55164 (15)	0.0616 (6)
H14A	−0.1582	0.3441	0.5205	0.092*
H14B	−0.1059	0.4562	0.5092	0.092*
H14C	−0.2165	0.4404	0.5647	0.092*
C15	0.22599 (15)	0.37969 (12)	0.95166 (11)	0.0332 (4)
C16	0.1496 (2)	0.41131 (15)	1.01546 (14)	0.0534 (5)
H16	0.0891	0.3662	1.0294	0.064*
C17	0.1618 (2)	0.50844 (17)	1.05846 (16)	0.0634 (6)
H17	0.1094	0.5278	1.1010	0.076*
C18	0.2498 (2)	0.57702 (16)	1.03973 (14)	0.0558 (5)
H18	0.2580	0.6429	1.0682	0.067*
C19	0.32474 (18)	0.54449 (15)	0.97744 (14)	0.0503 (5)
C20	0.31554 (16)	0.44858 (14)	0.93376 (12)	0.0437 (4)
H20	0.3693	0.4298	0.8922	0.052*

	U11	U22	U33	U12	U13	U23
F1	0.0871 (10)	0.0698 (9)	0.1120 (11)	−0.0351 (8)	0.0372 (9)	−0.0326 (8)
O1	0.0544 (8)	0.0560 (8)	0.0294 (6)	0.0148 (6)	0.0140 (5)	0.0112 (5)
O2	0.0456 (7)	0.0442 (7)	0.0505 (7)	0.0011 (5)	0.0255 (6)	0.0061 (6)
C1	0.0385 (9)	0.0287 (8)	0.0280 (8)	0.0023 (6)	0.0083 (6)	0.0000 (6)
C2	0.0345 (9)	0.0362 (9)	0.0338 (8)	0.0049 (7)	0.0043 (7)	0.0029 (7)
C3	0.0305 (8)	0.0338 (9)	0.0339 (8)	0.0066 (7)	0.0069 (6)	−0.0026 (7)
C4	0.0370 (9)	0.0426 (10)	0.0343 (8)	0.0091 (7)	0.0154 (7)	0.0055 (7)
C4A	0.0342 (8)	0.0258 (8)	0.0315 (8)	0.0057 (6)	0.0110 (6)	0.0037 (6)
C5	0.0414 (9)	0.0411 (9)	0.0304 (8)	0.0066 (7)	0.0085 (7)	0.0025 (7)
C5A	0.0339 (8)	0.0260 (8)	0.0316 (8)	0.0054 (6)	0.0104 (6)	0.0010 (6)
C6	0.0336 (9)	0.0433 (10)	0.0376 (9)	0.0076 (7)	0.0064 (7)	0.0030 (7)
C7	0.0336 (9)	0.0462 (10)	0.0520 (10)	−0.0009 (8)	0.0100 (8)	−0.0008 (8)
C8	0.0381 (9)	0.0236 (8)	0.0412 (9)	0.0013 (6)	0.0149 (7)	−0.0021 (7)
C8A	0.0357 (8)	0.0242 (7)	0.0321 (8)	0.0051 (6)	0.0118 (6)	0.0021 (6)
C9	0.0367 (8)	0.0301 (8)	0.0299 (8)	0.0071 (6)	0.0153 (6)	0.0063 (6)
C9A	0.0366 (8)	0.0263 (8)	0.0304 (8)	0.0063 (6)	0.0118 (6)	0.0024 (6)
N10	0.0359 (7)	0.0377 (7)	0.0282 (6)	0.0085 (6)	0.0143 (5)	0.0087 (6)
C11	0.0371 (10)	0.0608 (12)	0.0459 (10)	0.0141 (8)	0.0097 (8)	−0.0022 (9)
C12	0.0481 (11)	0.0399 (10)	0.0565 (11)	0.0047 (8)	0.0044 (9)	−0.0111 (8)
C13	0.0585 (12)	0.0388 (10)	0.0592 (12)	0.0117 (9)	0.0189 (9)	0.0052 (9)
C14	0.0457 (11)	0.0861 (16)	0.0504 (11)	0.0153 (11)	0.0015 (9)	0.0114 (11)
C15	0.0390 (9)	0.0343 (9)	0.0273 (8)	0.0102 (7)	0.0087 (6)	0.0035 (6)
C16	0.0703 (13)	0.0418 (10)	0.0577 (12)	0.0033 (9)	0.0375 (10)	−0.0041 (9)
C17	0.0827 (16)	0.0515 (12)	0.0660 (13)	0.0086 (11)	0.0410 (12)	−0.0144 (10)
C18	0.0690 (13)	0.0433 (11)	0.0550 (12)	0.0076 (10)	0.0108 (10)	−0.0158 (9)
C19	0.0508 (11)	0.0471 (11)	0.0525 (11)	−0.0065 (9)	0.0080 (9)	−0.0068 (9)
C20	0.0439 (10)	0.0485 (11)	0.0414 (9)	0.0020 (8)	0.0145 (8)	−0.0071 (8)

F1—C19	1.365 (2)	C8—C8A	1.453 (2)
O1—C1	1.2317 (18)	C8A—C9	1.514 (2)
O2—C8	1.2257 (18)	C9—C9A	1.508 (2)
C1—C9A	1.447 (2)	C9—C15	1.530 (2)
C1—C2	1.507 (2)	C9—H9	0.9800
C2—C3	1.531 (2)	N10—H10	0.8600
C2—H2A	0.9700	C11—H11A	0.9600
C2—H2B	0.9700	C11—H11B	0.9600
C3—C12	1.526 (2)	C11—H11C	0.9600
C3—C4	1.528 (2)	C12—H12A	0.9600
C3—C11	1.531 (2)	C12—H12B	0.9600
C4—C4A	1.498 (2)	C12—H12C	0.9600
C4—H4A	0.9700	C13—H13A	0.9600
C4—H4B	0.9700	C13—H13B	0.9600
C4A—C9A	1.358 (2)	C13—H13C	0.9600
C4A—N10	1.3766 (19)	C14—H14A	0.9600
C5—C5A	1.495 (2)	C14—H14B	0.9600
C5—C6	1.532 (2)	C14—H14C	0.9600
C5—H5A	0.9700	C15—C20	1.382 (2)
C5—H5B	0.9700	C15—C16	1.387 (2)
C5A—C8A	1.351 (2)	C16—C17	1.377 (3)
C5A—N10	1.3772 (19)	C16—H16	0.9300
C6—C7	1.525 (2)	C17—C18	1.369 (3)
C6—C13	1.529 (3)	C17—H17	0.9300
C6—C14	1.532 (2)	C18—C19	1.363 (3)
C7—C8	1.506 (2)	C18—H18	0.9300
C7—H7A	0.9700	C19—C20	1.367 (3)
C7—H7B	0.9700	C20—H20	0.9300
O1—C1—C9A	121.51 (14)	C8A—C9—C15	108.64 (12)
O1—C1—C2	120.49 (14)	C9A—C9—H9	108.7
C9A—C1—C2	117.97 (13)	C8A—C9—H9	108.7
C1—C2—C3	114.93 (13)	C15—C9—H9	108.7
C1—C2—H2A	108.5	C4A—C9A—C1	120.54 (14)
C3—C2—H2A	108.5	C4A—C9A—C9	120.86 (13)
C1—C2—H2B	108.5	C1—C9A—C9	118.53 (12)
C3—C2—H2B	108.5	C4A—N10—C5A	121.29 (12)
H2A—C2—H2B	107.5	C4A—N10—H10	119.4
C12—C3—C4	110.39 (14)	C5A—N10—H10	119.4
C12—C3—C11	109.23 (14)	C3—C11—H11A	109.5
C4—C3—C11	109.64 (14)	C3—C11—H11B	109.5
C12—C3—C2	110.11 (14)	H11A—C11—H11B	109.5
C4—C3—C2	108.35 (12)	C3—C11—H11C	109.5
C11—C3—C2	109.09 (13)	H11A—C11—H11C	109.5
C4A—C4—C3	112.70 (12)	H11B—C11—H11C	109.5
C4A—C4—H4A	109.1	C3—C12—H12A	109.5
C3—C4—H4A	109.1	C3—C12—H12B	109.5
C4A—C4—H4B	109.1	H12A—C12—H12B	109.5
C3—C4—H4B	109.1	C3—C12—H12C	109.5
H4A—C4—H4B	107.8	H12A—C12—H12C	109.5
C9A—C4A—N10	120.11 (13)	H12B—C12—H12C	109.5
C9A—C4A—C4	123.13 (14)	C6—C13—H13A	109.5
N10—C4A—C4	116.75 (12)	C6—C13—H13B	109.5
C5A—C5—C6	112.79 (13)	H13A—C13—H13B	109.5
C5A—C5—H5A	109.0	C6—C13—H13C	109.5
C6—C5—H5A	109.0	H13A—C13—H13C	109.5
C5A—C5—H5B	109.0	H13B—C13—H13C	109.5
C6—C5—H5B	109.0	C6—C14—H14A	109.5
H5A—C5—H5B	107.8	C6—C14—H14B	109.5
C8A—C5A—N10	120.17 (14)	H14A—C14—H14B	109.5
C8A—C5A—C5	123.37 (14)	C6—C14—H14C	109.5
N10—C5A—C5	116.45 (12)	H14A—C14—H14C	109.5
C7—C6—C13	110.98 (14)	H14B—C14—H14C	109.5
C7—C6—C14	109.44 (15)	C20—C15—C16	117.63 (16)
C13—C6—C14	109.17 (16)	C20—C15—C9	121.66 (13)
C7—C6—C5	107.34 (14)	C16—C15—C9	120.53 (15)
C13—C6—C5	110.50 (14)	C17—C16—C15	121.07 (19)
C14—C6—C5	109.37 (14)	C17—C16—H16	119.5
C8—C7—C6	114.23 (14)	C15—C16—H16	119.5
C8—C7—H7A	108.7	C18—C17—C16	121.17 (18)
C6—C7—H7A	108.7	C18—C17—H17	119.4
C8—C7—H7B	108.7	C16—C17—H17	119.4
C6—C7—H7B	108.7	C19—C18—C17	117.04 (18)
H7A—C7—H7B	107.6	C19—C18—H18	121.5
O2—C8—C8A	121.84 (15)	C17—C18—H18	121.5
O2—C8—C7	120.85 (15)	C18—C19—F1	118.19 (17)
C8A—C8—C7	117.28 (13)	C18—C19—C20	123.36 (19)
C5A—C8A—C8	120.10 (14)	F1—C19—C20	118.45 (17)
C5A—C8A—C9	120.50 (14)	C19—C20—C15	119.71 (16)
C8—C8A—C9	119.38 (12)	C19—C20—H20	120.1
C9A—C9—C8A	109.52 (12)	C15—C20—H20	120.1
C9A—C9—C15	112.41 (13)
O1—C1—C2—C3	153.20 (15)	C8—C8A—C9—C15	−83.98 (16)
C9A—C1—C2—C3	−28.8 (2)	N10—C4A—C9A—C1	177.60 (14)
C1—C2—C3—C12	−69.81 (17)	C4—C4A—C9A—C1	−3.2 (2)
C1—C2—C3—C4	51.02 (18)	N10—C4A—C9A—C9	−5.5 (2)
C1—C2—C3—C11	170.33 (14)	C4—C4A—C9A—C9	173.74 (15)
C12—C3—C4—C4A	71.15 (17)	O1—C1—C9A—C4A	−178.70 (15)
C11—C3—C4—C4A	−168.46 (14)	C2—C1—C9A—C4A	3.3 (2)
C2—C3—C4—C4A	−49.50 (18)	O1—C1—C9A—C9	4.3 (2)
C3—C4—C4A—C9A	27.9 (2)	C2—C1—C9A—C9	−173.69 (14)
C3—C4—C4A—N10	−152.80 (14)	C8A—C9—C9A—C4A	25.2 (2)
C6—C5—C5A—C8A	19.5 (2)	C15—C9—C9A—C4A	−95.64 (17)
C6—C5—C5A—N10	−161.31 (14)	C8A—C9—C9A—C1	−157.80 (13)
C5A—C5—C6—C7	−49.58 (19)	C15—C9—C9A—C1	81.32 (17)
C5A—C5—C6—C13	71.57 (18)	C9A—C4A—N10—C5A	−14.6 (2)
C5A—C5—C6—C14	−168.23 (15)	C4—C4A—N10—C5A	166.08 (14)
C13—C6—C7—C8	−66.14 (19)	C8A—C5A—N10—C4A	11.1 (2)
C14—C6—C7—C8	173.31 (15)	C5—C5A—N10—C4A	−168.07 (14)
C5—C6—C7—C8	54.70 (19)	C9A—C9—C15—C20	33.0 (2)
C6—C7—C8—O2	153.47 (15)	C8A—C9—C15—C20	−88.35 (18)
C6—C7—C8—C8A	−28.6 (2)	C9A—C9—C15—C16	−152.02 (16)
N10—C5A—C8A—C8	−169.29 (14)	C8A—C9—C15—C16	86.61 (18)
C5—C5A—C8A—C8	9.8 (2)	C20—C15—C16—C17	0.7 (3)
N10—C5A—C8A—C9	12.3 (2)	C9—C15—C16—C17	−174.41 (18)
C5—C5A—C8A—C9	−168.58 (14)	C15—C16—C17—C18	0.0 (3)
O2—C8—C8A—C5A	172.64 (15)	C16—C17—C18—C19	−0.4 (3)
C7—C8—C8A—C5A	−5.3 (2)	C17—C18—C19—F1	179.82 (19)
O2—C8—C8A—C9	−8.9 (2)	C17—C18—C19—C20	0.2 (3)
C7—C8—C8A—C9	173.17 (14)	C18—C19—C20—C15	0.5 (3)
C5A—C8A—C9—C9A	−28.68 (19)	F1—C19—C20—C15	−179.10 (16)
C8—C8A—C9—C9A	152.89 (13)	C16—C15—C20—C19	−1.0 (3)
C5A—C8A—C9—C15	94.45 (16)	C9—C15—C20—C19	174.13 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10···O1i	0.86	2.14	2.990 (2)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H10⋯O1i	0.86	2.14	2.990 (2)	168

Symmetry code: (i) .