1-[4-(2-Amino-anilino)phen-yl]-2,2,2-trifluoro-ethanone.

In the title compound, C(14)H(11)F(3)N(2)O, the two aromatic rings are oriented at a dihedral angle of 70.84 (8)°. The crystal structure displays inter-molecular N-H⋯O and N-H⋯F inter-actions.

Related literature

For 2,2,2-trifluoroacetophenones as intermediates for further Buchwald–Hartwig coupling, see: Colard et al. (1994 ▶); Schenck et al. (2004 ▶).

Experimental

Crystal data

C14H11F3N2O

M = 280.25

Orthorhombic,

a = 13.0385 (13) Å

b = 8.7129 (7) Å

c = 22.424 (2) Å

V = 2547.4 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 173 K

0.4 × 0.3 × 0.2 mm

Data collection

Bruker SMART APEXII diffractometer

21134 measured reflections

3033 independent reflections

2498 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.127

S = 1.06

3033 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810008937/bt5212sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008937/bt5212Isup2.hkl

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

C14H11F3N2O	F(000) = 1152
Mr = 280.25	Dx = 1.461 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7908 reflections
a = 13.0385 (13) Å	θ = 2.4–27.7°
b = 8.7129 (7) Å	µ = 0.12 mm−1
c = 22.424 (2) Å	T = 173 K
V = 2547.4 (4) Å3	Block, brown
Z = 8	0.4 × 0.3 × 0.2 mm

Bruker SMART APEXII diffractometer	2498 reflections with I > 2σ(I)
Radiation source: sealed Tube	Rint = 0.026
graphite	θmax = 27.9°, θmin = 1.8°
CCD scan	h = −17→17
21134 measured reflections	k = −11→8
3033 independent reflections	l = −29→29

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0601P)2 + 1.4118P] where P = (Fo2 + 2Fc2)/3
3033 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.67 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.18780 (11)	0.80106 (18)	0.63368 (7)	0.0277 (3)
C2	0.19637 (13)	0.7530 (2)	0.69312 (7)	0.0330 (4)
C3	0.11693 (16)	0.7953 (2)	0.73256 (8)	0.0479 (5)
H3	0.1203	0.7641	0.7731	0.057*
C4	0.03490 (16)	0.8806 (3)	0.71344 (11)	0.0580 (6)
H4	−0.0181	0.9060	0.7408	0.070*
C5	0.02813 (15)	0.9299 (3)	0.65535 (11)	0.0546 (6)
H5	−0.0282	0.9908	0.6427	0.065*
C6	0.10447 (13)	0.8895 (2)	0.61572 (8)	0.0381 (4)
H6	0.1000	0.9226	0.5754	0.046*
N7	0.27946 (14)	0.6728 (2)	0.71200 (7)	0.0486 (4)
H7A	0.3249	0.6275	0.6871	0.073*
H7B	0.2675	0.6308	0.7483	0.073*
N8	0.26108 (10)	0.75201 (16)	0.59059 (5)	0.0291 (3)
H8	0.2297	0.6912	0.5600	0.035*
C9	0.35838 (11)	0.80793 (18)	0.58519 (6)	0.0255 (3)
C10	0.39963 (12)	0.91396 (18)	0.62580 (6)	0.0271 (3)
H10	0.3594	0.9488	0.6584	0.033*
C11	0.49855 (12)	0.96782 (18)	0.61856 (6)	0.0272 (3)
H11	0.5256	1.0394	0.6464	0.033*
C12	0.55966 (11)	0.91856 (17)	0.57084 (6)	0.0253 (3)
C13	0.51717 (12)	0.81270 (19)	0.53022 (6)	0.0284 (3)
H13	0.5571	0.7789	0.4973	0.034*
C14	0.41990 (12)	0.75778 (19)	0.53712 (6)	0.0288 (3)
H14	0.3934	0.6854	0.5094	0.035*
C15	0.66340 (11)	0.97035 (18)	0.55983 (6)	0.0266 (3)
O16	0.71615 (9)	0.93617 (15)	0.51702 (5)	0.0362 (3)
C17	0.71528 (12)	1.0765 (2)	0.60606 (7)	0.0322 (3)
F18	0.81079 (8)	1.10979 (14)	0.59054 (5)	0.0480 (3)
F19	0.72009 (9)	1.00909 (14)	0.65988 (4)	0.0457 (3)
F20	0.66562 (9)	1.20895 (13)	0.61292 (6)	0.0490 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0266 (7)	0.0279 (8)	0.0286 (7)	−0.0045 (6)	0.0007 (5)	−0.0050 (6)
C2	0.0395 (9)	0.0301 (8)	0.0294 (7)	−0.0087 (7)	0.0016 (6)	−0.0028 (6)
C3	0.0580 (12)	0.0506 (12)	0.0350 (9)	−0.0185 (9)	0.0134 (8)	−0.0102 (8)
C4	0.0368 (10)	0.0683 (15)	0.0690 (14)	−0.0087 (10)	0.0175 (9)	−0.0283 (12)
C5	0.0323 (9)	0.0582 (13)	0.0731 (15)	0.0060 (9)	−0.0043 (9)	−0.0257 (11)
C6	0.0323 (8)	0.0357 (9)	0.0461 (9)	−0.0009 (7)	−0.0083 (7)	−0.0099 (7)
N7	0.0645 (11)	0.0484 (10)	0.0328 (7)	0.0107 (8)	−0.0015 (7)	0.0043 (7)
N8	0.0285 (6)	0.0334 (7)	0.0254 (6)	−0.0031 (5)	−0.0012 (5)	−0.0067 (5)
C9	0.0268 (7)	0.0262 (7)	0.0235 (6)	0.0018 (6)	−0.0019 (5)	0.0023 (5)
C10	0.0291 (7)	0.0277 (8)	0.0246 (6)	0.0013 (6)	0.0031 (5)	−0.0041 (6)
C11	0.0300 (7)	0.0265 (8)	0.0252 (7)	−0.0009 (6)	0.0008 (5)	−0.0049 (6)
C12	0.0270 (7)	0.0265 (8)	0.0225 (6)	0.0027 (6)	0.0004 (5)	0.0005 (5)
C13	0.0315 (7)	0.0329 (8)	0.0208 (6)	0.0051 (6)	0.0011 (5)	−0.0029 (6)
C14	0.0334 (7)	0.0309 (8)	0.0221 (6)	0.0005 (6)	−0.0032 (6)	−0.0047 (6)
C15	0.0277 (7)	0.0272 (8)	0.0250 (7)	0.0041 (6)	0.0003 (5)	0.0019 (6)
O16	0.0313 (6)	0.0471 (7)	0.0302 (6)	0.0038 (5)	0.0073 (4)	−0.0043 (5)
C17	0.0301 (8)	0.0333 (9)	0.0331 (8)	−0.0041 (6)	0.0044 (6)	−0.0016 (6)
F18	0.0326 (5)	0.0561 (7)	0.0552 (7)	−0.0143 (5)	0.0085 (5)	−0.0073 (5)
F19	0.0530 (7)	0.0552 (7)	0.0289 (5)	−0.0147 (5)	−0.0056 (4)	−0.0012 (4)
F20	0.0485 (6)	0.0319 (6)	0.0667 (7)	−0.0023 (5)	0.0089 (5)	−0.0128 (5)

C1—C6	1.391 (2)	C9—C10	1.404 (2)
C1—C2	1.402 (2)	C9—C14	1.413 (2)
C1—N8	1.4244 (19)	C10—C11	1.382 (2)
C2—N7	1.357 (2)	C10—H10	0.9500
C2—C3	1.411 (2)	C11—C12	1.402 (2)
C3—C4	1.371 (3)	C11—H11	0.9500
C3—H3	0.9500	C12—C13	1.410 (2)
C4—C5	1.374 (4)	C12—C15	1.447 (2)
C4—H4	0.9500	C13—C14	1.364 (2)
C5—C6	1.380 (3)	C13—H13	0.9500
C5—H5	0.9500	C14—H14	0.9500
C6—H6	0.9500	C15—O16	1.2180 (18)
N7—H7A	0.9044	C15—C17	1.545 (2)
N7—H7B	0.9069	C17—F18	1.3251 (18)
N8—C9	1.364 (2)	C17—F20	1.332 (2)
N8—H8	0.9582	C17—F19	1.3437 (19)
C6—C1—C2	120.18 (15)	C10—C9—C14	118.74 (14)
C6—C1—N8	119.58 (15)	C11—C10—C9	120.30 (13)
C2—C1—N8	120.13 (14)	C11—C10—H10	119.8
N7—C2—C1	120.94 (15)	C9—C10—H10	119.8
N7—C2—C3	121.67 (16)	C10—C11—C12	121.08 (14)
C1—C2—C3	117.36 (17)	C10—C11—H11	119.5
C4—C3—C2	121.20 (19)	C12—C11—H11	119.5
C4—C3—H3	119.4	C11—C12—C13	118.05 (14)
C2—C3—H3	119.4	C11—C12—C15	124.48 (14)
C3—C4—C5	121.06 (18)	C13—C12—C15	117.46 (13)
C3—C4—H4	119.5	C14—C13—C12	121.44 (13)
C5—C4—H4	119.5	C14—C13—H13	119.3
C4—C5—C6	119.0 (2)	C12—C13—H13	119.3
C4—C5—H5	120.5	C13—C14—C9	120.38 (14)
C6—C5—H5	120.5	C13—C14—H14	119.8
C5—C6—C1	121.21 (18)	C9—C14—H14	119.8
C5—C6—H6	119.4	O16—C15—C12	125.88 (14)
C1—C6—H6	119.4	O16—C15—C17	115.33 (14)
C2—N7—H7A	123.8	C12—C15—C17	118.78 (13)
C2—N7—H7B	110.6	F18—C17—F20	107.33 (14)
H7A—N7—H7B	119.4	F18—C17—F19	106.72 (14)
C9—N8—C1	125.23 (12)	F20—C17—F19	107.33 (13)
C9—N8—H8	122.1	F18—C17—C15	111.47 (13)
C1—N8—H8	111.3	F20—C17—C15	112.54 (13)
N8—C9—C10	122.24 (13)	F19—C17—C15	111.16 (13)
N8—C9—C14	119.02 (13)
C6—C1—C2—N7	−176.94 (16)	C10—C11—C12—C13	0.2 (2)
N8—C1—C2—N7	6.8 (2)	C10—C11—C12—C15	179.43 (14)
C6—C1—C2—C3	1.2 (2)	C11—C12—C13—C14	−0.7 (2)
N8—C1—C2—C3	−175.01 (15)	C15—C12—C13—C14	−179.98 (14)
N7—C2—C3—C4	177.89 (19)	C12—C13—C14—C9	0.9 (2)
C1—C2—C3—C4	−0.3 (3)	N8—C9—C14—C13	179.40 (14)
C2—C3—C4—C5	−1.1 (3)	C10—C9—C14—C13	−0.5 (2)
C3—C4—C5—C6	1.4 (3)	C11—C12—C15—O16	−175.65 (16)
C4—C5—C6—C1	−0.4 (3)	C13—C12—C15—O16	3.6 (2)
C2—C1—C6—C5	−0.9 (3)	C11—C12—C15—C17	5.5 (2)
N8—C1—C6—C5	175.34 (17)	C13—C12—C15—C17	−175.33 (14)
C6—C1—N8—C9	107.87 (18)	O16—C15—C17—F18	−1.0 (2)
C2—C1—N8—C9	−75.9 (2)	C12—C15—C17—F18	178.04 (14)
C1—N8—C9—C10	5.3 (2)	O16—C15—C17—F20	119.68 (16)
C1—N8—C9—C14	−174.67 (15)	C12—C15—C17—F20	−61.32 (19)
N8—C9—C10—C11	−179.88 (14)	O16—C15—C17—F19	−119.90 (15)
C14—C9—C10—C11	0.1 (2)	C12—C15—C17—F19	59.11 (19)
C9—C10—C11—C12	0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7B···F19i	0.91	2.32	3.2077 (19)	166
N8—H8···O16ii	0.96	2.06	2.9757 (17)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7B⋯F19i	0.91	2.32	3.2077 (19)	166
N8—H8⋯O16ii	0.96	2.06	2.9757 (17)	159

Symmetry codes: (i) ; (ii) .