5,7-Dibromo-3-trifluoro-methyl-3,4-dihydro-acridin-1(2H)-one.

In the title compound, C(14)H(8)Br(2)F(3)NO, the mol-ecule is disordered across an approximate non-crystallographic mirror plane, which is in the plane of the fused ring system [The tetrahedral C atom bearing the trifluormethyl substituent is disordered with site occupancy factors of 0.80 (2) and 0.20 (2)]. In the crystal, a one-dimensional stacking of mol-ecules involves inter-actions between the pyridine ring and symmetry-related Br and O atoms of adjacent mol-ecules. The stacking distance between the mean planes of adjacent mol-ecules is 3.395 (4) Å.

Related literature

For the anti­cancer activity of the title compound, see: Fadeyi et al. (2008 ▶). For fluorinated acridones, see: Fadeyi et al. (2008 ▶); Mayur et al. (2009 ▶); Svyatkina et al. (1988 ▶). For a related structure, see: Martinez et al. (1995 ▶).

Experimental

Crystal data

C14H8Br2F3NO

M = 423.03

Triclinic,

a = 5.3303 (10) Å

b = 10.926 (2) Å

c = 12.354 (2) Å

α = 83.349 (6)°

β = 85.741 (6)°

γ = 85.051 (6)°

V = 710.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 5.74 mm−1

T = 293 K

0.21 × 0.13 × 0.06 mm

Data collection

Rigaku XtaLAB mini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 1999 ▶; Pflugrath, 1999 ▶) T min = 0.379, T max = 0.725

4444 measured reflections

3153 independent reflections

2188 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.134

S = 0.97

3153 reflections

217 parameters

34 restraints

H-atom parameters constrained

Δρmax = 0.80 e Å−3

Δρmin = −0.67 e Å−3

Data collection: CrystalClear (Rigaku, 1999 ▶; Pflugrath, 1999 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) as included in WinGX (Farrugia, 1999 ▶); software used to prepare material for publication: WinGX and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811027516/pk2334sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027516/pk2334Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811027516/pk2334Isup3.cml

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

C14H8Br2F3NO	Z = 2
Mr = 423.03	F(000) = 408
Triclinic, P1	Dx = 1.977 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3303 (10) Å	Cell parameters from 3749 reflections
b = 10.926 (2) Å	θ = 3.3–27.6°
c = 12.354 (2) Å	µ = 5.74 mm−1
α = 83.349 (6)°	T = 293 K
β = 85.741 (6)°	Prism, colorless
γ = 85.051 (6)°	0.21 × 0.13 × 0.06 mm
V = 710.5 (2) Å3

Rigaku XtaLAB mini diffractometer	2188 reflections with I > 2σ(I)
graphite	Rint = 0.050
ω scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (CrystalClear; Rigaku, 1999; Pflugrath, 1999)	h = −3→6
Tmin = 0.379, Tmax = 0.725	k = −14→14
4444 measured reflections	l = −15→15
3153 independent 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0643P)2] where P = (Fo2 + 2Fc2)/3
3153 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.80 e Å−3
34 restraints	Δρmin = −0.67 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
Br1	−0.08381 (9)	0.38272 (5)	0.91649 (4)	0.05150 (19)
Br2	0.25701 (14)	0.07810 (5)	0.58890 (5)	0.0731 (2)
N1	0.3349 (7)	0.5389 (3)	0.8099 (3)	0.0420 (9)
O1	1.0453 (7)	0.6599 (4)	0.5769 (3)	0.0583 (10)
C1	0.8841 (9)	0.6822 (5)	0.6495 (4)	0.0455 (11)
C2	0.875 (2)	0.7995 (11)	0.7024 (11)	0.051 (3)	0.796 (6)
H2A	0.7635	0.8621	0.6642	0.061*	0.796 (6)
H2B	1.0423	0.8292	0.6969	0.061*	0.796 (6)
C3	0.7812 (11)	0.7788 (5)	0.8223 (5)	0.0418 (14)	0.796 (6)
H3	0.8977	0.7168	0.8602	0.05*	0.796 (6)
C11	0.770 (2)	0.8972 (8)	0.8778 (9)	0.056 (2)	0.796 (6)
F1	0.6920 (9)	0.8785 (4)	0.9826 (3)	0.0747 (14)	0.796 (6)
F2	1.0046 (8)	0.9352 (4)	0.8774 (4)	0.0779 (15)	0.796 (6)
F3	0.6313 (10)	0.9893 (4)	0.8297 (4)	0.0829 (18)	0.796 (6)
C4	0.519 (3)	0.7294 (10)	0.8318 (9)	0.048 (3)	0.796 (6)
H4A	0.4667	0.7103	0.9084	0.058*	0.796 (6)
H4B	0.3987	0.7933	0.8007	0.058*	0.796 (6)
C2'	0.897 (9)	0.779 (5)	0.718 (5)	0.051 (3)	0.204 (6)
H2'1	0.9643	0.8496	0.6739	0.061*	0.204 (6)
H2'2	1.0123	0.7504	0.7741	0.061*	0.204 (6)
C3'	0.641 (4)	0.8190 (18)	0.7713 (17)	0.044 (5)*	0.204 (6)
H3'	0.5204	0.8398	0.7148	0.053*	0.204 (6)
C11'	0.661 (4)	0.933 (2)	0.831 (2)	0.058 (7)*	0.204 (6)
F1'	0.442 (3)	0.9642 (17)	0.8836 (14)	0.084 (6)*	0.204 (6)
F2'	0.828 (6)	0.897 (3)	0.910 (2)	0.095 (12)*	0.204 (6)
F3'	0.754 (4)	1.0247 (17)	0.7699 (17)	0.093 (7)*	0.204 (6)
C4'	0.546 (13)	0.714 (4)	0.853 (5)	0.048 (3)	0.204 (6)
H4'1	0.3875	0.7386	0.8911	0.058*	0.204 (6)
H4'2	0.6692	0.6838	0.9059	0.058*	0.204 (6)
C4A	0.5120 (8)	0.6143 (4)	0.7741 (4)	0.0421 (11)
C5	0.1374 (9)	0.3514 (4)	0.7950 (4)	0.0426 (10)
C6	0.1224 (9)	0.2471 (4)	0.7460 (4)	0.0489 (12)
H6	0.0023	0.1921	0.7718	0.059*
C7	0.2894 (10)	0.2233 (4)	0.6562 (4)	0.0506 (12)
C8	0.4680 (10)	0.3008 (4)	0.6163 (4)	0.0498 (12)
H8	0.5753	0.2832	0.5563	0.06*
C8A	0.4892 (9)	0.4080 (4)	0.6668 (3)	0.0410 (10)
C9	0.6745 (9)	0.4917 (4)	0.6312 (4)	0.0436 (11)
H9	0.7869	0.4772	0.5719	0.052*
C9A	0.6878 (9)	0.5944 (4)	0.6845 (3)	0.0410 (10)
C10A	0.3249 (8)	0.4357 (4)	0.7576 (4)	0.0408 (10)

	U11	U22	U33	U12	U13	U23
Br1	0.0544 (3)	0.0519 (3)	0.0473 (3)	−0.0081 (2)	0.0128 (2)	−0.0092 (2)
Br2	0.1173 (6)	0.0430 (3)	0.0626 (4)	−0.0170 (3)	0.0078 (3)	−0.0210 (3)
N1	0.042 (2)	0.043 (2)	0.042 (2)	−0.0072 (18)	0.0037 (17)	−0.0121 (17)
O1	0.058 (2)	0.060 (2)	0.056 (2)	−0.0144 (18)	0.0230 (18)	−0.0146 (18)
C1	0.043 (2)	0.044 (3)	0.048 (3)	−0.002 (2)	0.002 (2)	−0.005 (2)
C2	0.053 (4)	0.047 (5)	0.053 (5)	−0.008 (3)	0.011 (4)	−0.011 (4)
C3	0.048 (3)	0.034 (3)	0.044 (3)	−0.009 (3)	0.007 (3)	−0.010 (2)
C11	0.057 (5)	0.044 (4)	0.069 (5)	−0.007 (3)	0.007 (5)	−0.018 (4)
F1	0.104 (3)	0.064 (3)	0.061 (2)	−0.014 (2)	0.013 (2)	−0.035 (2)
F2	0.070 (3)	0.073 (3)	0.099 (3)	−0.021 (2)	0.009 (2)	−0.046 (3)
F3	0.107 (4)	0.046 (3)	0.097 (4)	0.017 (3)	−0.016 (3)	−0.026 (3)
C4	0.042 (4)	0.060 (4)	0.049 (6)	−0.009 (4)	0.005 (4)	−0.026 (4)
C2'	0.053 (4)	0.047 (5)	0.053 (5)	−0.008 (3)	0.011 (4)	−0.011 (4)
C4'	0.042 (4)	0.060 (4)	0.049 (6)	−0.009 (4)	0.005 (4)	−0.026 (4)
C4A	0.042 (2)	0.042 (3)	0.043 (2)	−0.003 (2)	−0.001 (2)	−0.013 (2)
C5	0.046 (2)	0.045 (3)	0.037 (2)	−0.002 (2)	−0.0009 (19)	−0.008 (2)
C6	0.058 (3)	0.042 (3)	0.046 (3)	−0.009 (2)	0.002 (2)	−0.001 (2)
C7	0.072 (3)	0.034 (3)	0.047 (3)	−0.002 (2)	0.000 (2)	−0.011 (2)
C8	0.061 (3)	0.046 (3)	0.042 (3)	−0.001 (2)	0.006 (2)	−0.011 (2)
C8A	0.050 (3)	0.042 (3)	0.032 (2)	−0.003 (2)	0.0028 (19)	−0.0085 (19)
C9	0.048 (3)	0.044 (3)	0.036 (2)	0.002 (2)	0.011 (2)	−0.007 (2)
C9A	0.045 (2)	0.040 (3)	0.038 (2)	−0.002 (2)	0.001 (2)	−0.009 (2)
C10A	0.045 (3)	0.038 (2)	0.038 (2)	0.000 (2)	0.001 (2)	−0.0072 (19)

Br1—C5	1.884 (4)	C2'—H2'2	0.97
Br2—C7	1.901 (5)	C3'—C4'	1.54 (2)
N1—C4A	1.325 (6)	C3'—C11'	1.538 (19)
N1—C10A	1.369 (5)	C3'—H3'	0.98
O1—C1	1.226 (5)	C11'—F3'	1.29 (2)
C1—C2'	1.43 (5)	C11'—F1'	1.33 (2)
C1—C9A	1.487 (7)	C11'—F2'	1.37 (2)
C1—C2	1.499 (13)	C4'—C4A	1.57 (6)
C2—C3	1.526 (11)	C4'—H4'1	0.97
C2—H2A	0.97	C4'—H4'2	0.97
C2—H2B	0.97	C4A—C9A	1.420 (6)
C3—C11	1.527 (9)	C5—C6	1.361 (6)
C3—C4	1.535 (13)	C5—C10A	1.433 (6)
C3—H3	0.98	C6—C7	1.403 (6)
C11—F3	1.307 (12)	C6—H6	0.93
C11—F1	1.327 (11)	C7—C8	1.356 (7)
C11—F2	1.353 (11)	C8—C8A	1.406 (6)
C4—C4A	1.519 (13)	C8—H8	0.93
C4—H4A	0.97	C8A—C9	1.415 (7)
C4—H4B	0.97	C8A—C10A	1.416 (6)
C2'—C3'	1.52 (2)	C9—C9A	1.375 (6)
C2'—H2'1	0.97	C9—H9	0.93
C4A—N1—C10A	117.5 (4)	F3'—C11'—F1'	113 (2)
O1—C1—C2'	123.2 (16)	F3'—C11'—F2'	106 (2)
O1—C1—C9A	120.2 (5)	F1'—C11'—F2'	106 (2)
C2'—C1—C9A	115.7 (16)	F3'—C11'—C3'	113.6 (19)
O1—C1—C2	121.1 (5)	F1'—C11'—C3'	110.7 (17)
C9A—C1—C2	118.6 (5)	F2'—C11'—C3'	106 (2)
C1—C2—C3	111.0 (8)	C3'—C4'—C4A	101 (3)
C1—C2—H2A	109.4	C3'—C4'—H4'1	111.6
C3—C2—H2A	109.4	C4A—C4'—H4'1	111.6
C1—C2—H2B	109.4	C3'—C4'—H4'2	111.6
C3—C2—H2B	109.4	C4A—C4'—H4'2	111.6
H2A—C2—H2B	108	H4'1—C4'—H4'2	109.4
C2—C3—C11	112.0 (7)	N1—C4A—C9A	123.6 (4)
C2—C3—C4	109.8 (8)	N1—C4A—C4	116.9 (5)
C11—C3—C4	109.5 (6)	C9A—C4A—C4	119.5 (5)
C2—C3—H3	108.5	N1—C4A—C4'	113.6 (13)
C11—C3—H3	108.5	C9A—C4A—C4'	121.7 (16)
C4—C3—H3	108.5	C6—C5—C10A	120.9 (4)
F3—C11—F1	109.6 (7)	C6—C5—Br1	119.7 (4)
F3—C11—F2	106.5 (7)	C10A—C5—Br1	119.4 (3)
F1—C11—F2	104.9 (10)	C5—C6—C7	119.6 (5)
F3—C11—C3	113.9 (9)	C5—C6—H6	120.2
F1—C11—C3	111.9 (6)	C7—C6—H6	120.2
F2—C11—C3	109.5 (6)	C8—C7—C6	122.1 (4)
C4A—C4—C3	112.7 (8)	C8—C7—Br2	119.9 (4)
C4A—C4—H4A	109.1	C6—C7—Br2	118.0 (4)
C3—C4—H4A	109.1	C7—C8—C8A	119.2 (4)
C4A—C4—H4B	109.1	C7—C8—H8	120.4
C3—C4—H4B	109.1	C8A—C8—H8	120.4
H4A—C4—H4B	107.8	C8—C8A—C9	122.4 (4)
C1—C2'—C3'	113 (4)	C8—C8A—C10A	120.6 (4)
C1—C2'—H2'1	109	C9—C8A—C10A	117.0 (4)
C3'—C2'—H2'1	109	C9A—C9—C8A	119.8 (4)
C1—C2'—H2'2	109	C9A—C9—H9	120.1
C3'—C2'—H2'2	109	C8A—C9—H9	120.1
H2'1—C2'—H2'2	107.8	C9—C9A—C4A	118.7 (4)
C2'—C3'—C4'	110 (2)	C9—C9A—C1	120.6 (4)
C2'—C3'—C11'	110 (2)	C4A—C9A—C1	120.7 (4)
C4'—C3'—C11'	109 (2)	N1—C10A—C8A	123.4 (4)
C2'—C3'—H3'	108.9	N1—C10A—C5	119.0 (4)
C4'—C3'—H3'	108.9	C8A—C10A—C5	117.6 (4)
C11'—C3'—H3'	108.9
O1—C1—C2—C3	−147.1 (7)	C10A—C5—C6—C7	−1.3 (7)
C2'—C1—C2—C3	−43 (9)	Br1—C5—C6—C7	−179.3 (4)
C9A—C1—C2—C3	34.9 (12)	C5—C6—C7—C8	0.3 (8)
C1—C2—C3—C11	−179.8 (8)	C5—C6—C7—Br2	−178.9 (4)
C1—C2—C3—C4	−58.0 (11)	C6—C7—C8—C8A	0.6 (8)
C2—C3—C11—F3	56.1 (10)	Br2—C7—C8—C8A	179.8 (4)
C4—C3—C11—F3	−65.8 (9)	C7—C8—C8A—C9	178.6 (5)
C2—C3—C11—F1	−178.9 (10)	C7—C8—C8A—C10A	−0.6 (7)
C4—C3—C11—F1	59.1 (11)	C8—C8A—C9—C9A	−179.3 (4)
C2—C3—C11—F2	−63.0 (11)	C10A—C8A—C9—C9A	−0.2 (7)
C4—C3—C11—F2	175.0 (8)	C8A—C9—C9A—C4A	−0.5 (7)
C2—C3—C4—C4A	54.2 (10)	C8A—C9—C9A—C1	178.9 (4)
C11—C3—C4—C4A	177.5 (7)	N1—C4A—C9A—C9	0.2 (7)
O1—C1—C2'—C3'	159 (2)	C4—C4A—C9A—C9	−178.2 (7)
C9A—C1—C2'—C3'	−32 (5)	C4'—C4A—C9A—C9	168 (3)
C2—C1—C2'—C3'	76 (10)	N1—C4A—C9A—C1	−179.1 (4)
C1—C2'—C3'—C4'	66 (5)	C4—C4A—C9A—C1	2.5 (9)
C1—C2'—C3'—C11'	−173 (3)	C4'—C4A—C9A—C1	−12 (3)
C2'—C3'—C11'—F3'	55 (4)	O1—C1—C9A—C9	−4.2 (7)
C4'—C3'—C11'—F3'	176 (3)	C2'—C1—C9A—C9	−174 (3)
C2'—C3'—C11'—F1'	−176 (3)	C2—C1—C9A—C9	173.8 (7)
C4'—C3'—C11'—F1'	−55 (4)	O1—C1—C9A—C4A	175.2 (4)
C2'—C3'—C11'—F2'	−61 (4)	C2'—C1—C9A—C4A	6(3)
C4'—C3'—C11'—F2'	60 (4)	C2—C1—C9A—C4A	−6.8 (9)
C2'—C3'—C4'—C4A	−64 (5)	C4A—N1—C10A—C8A	−1.5 (7)
C11'—C3'—C4'—C4A	174 (3)	C4A—N1—C10A—C5	179.4 (4)
C10A—N1—C4A—C9A	0.7 (7)	C8—C8A—C10A—N1	−179.6 (4)
C10A—N1—C4A—C4	179.2 (7)	C9—C8A—C10A—N1	1.2 (7)
C10A—N1—C4A—C4'	−168 (3)	C8—C8A—C10A—C5	−0.4 (7)
C3—C4—C4A—N1	154.8 (6)	C9—C8A—C10A—C5	−179.6 (4)
C3—C4—C4A—C9A	−26.7 (11)	C6—C5—C10A—N1	−179.4 (4)
C3—C4—C4A—C4'	77 (10)	Br1—C5—C10A—N1	−1.5 (6)
C3'—C4'—C4A—N1	−152 (2)	C6—C5—C10A—C8A	1.4 (7)
C3'—C4'—C4A—C9A	40 (5)	Br1—C5—C10A—C8A	179.3 (3)
C3'—C4'—C4A—C4	−43 (7)