2,5-Dimethyl-3-[4-(trifluoro-meth-oxy)anilino]-cyclo-hex-2-enone.

In the title compound, C(15)H(16)F(3)NO(2), the dihedral angle between the benzene ring and the conjugated part of the cyclo-hexene ring is 60.00 (8)°. The non-conjugated part of the cyclohexene ring and the trifluoro-methyl group are both disordered over two sets of sites with occupancies of 0.835 (2) and 0.165 (2). In the crystal, mol-ecules are linked into chains along [010] by inter-molecular N-H⋯O hydrogen bonds. Weak inter-molecular C-H⋯O inter-actions also occur.

Related literature

For the anti­convulsant properties of enamino­nes, see: Alexander et al. (2010 ▶, 2011 ▶); Edafiogho et al. (1992 ▶); Eddington et al. (2003 ▶); North et al. (2011 ▶); Scott et al. (1993 ▶, 1995 ▶). For related structures see: Alexander et al. (2010 ▶, 2011 ▶); North et al. (2011 ▶); Scott et al. (2006a ▶,b ▶).

Experimental

Crystal data

C15H16F3NO2

M = 299.29

Monoclinic,

a = 6.10302 (11) Å

b = 8.39246 (16) Å

c = 28.2487 (5) Å

β = 93.6941 (16)°

V = 1443.88 (5) Å3

Z = 4

Cu Kα radiation

μ = 1.01 mm−1

T = 123 K

0.52 × 0.36 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.697, T max = 1.000

5270 measured reflections

2843 independent reflections

2624 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.138

S = 1.05

2843 reflections

219 parameters

48 restraints

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.50 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811004338/lh5206sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004338/lh5206Isup2.hkl

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

C15H16F3NO2	F(000) = 624
Mr = 299.29	Dx = 1.377 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 4019 reflections
a = 6.10302 (11) Å	θ = 4.7–74.0°
b = 8.39246 (16) Å	µ = 1.01 mm−1
c = 28.2487 (5) Å	T = 123 K
β = 93.6941 (16)°	Plate, colorless
V = 1443.88 (5) Å3	0.52 × 0.36 × 0.12 mm
Z = 4

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2843 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2624 reflections with I > 2σ(I)
graphite	Rint = 0.016
Detector resolution: 10.5081 pixels mm-1	θmax = 74.2°, θmin = 5.5°
ω scans	h = −4→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −9→10
Tmin = 0.697, Tmax = 1.000	l = −34→34
5270 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0709P)2 + 0.9652P] where P = (Fo2 + 2Fc2)/3
2843 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.65 e Å−3
48 restraints	Δρmin = −0.50 e Å−3

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	Occ. (<1)
C7A	0.7405 (3)	1.2972 (3)	0.48394 (6)	0.0462 (7)	0.835 (2)
F1A	0.7047 (3)	1.3585 (5)	0.52573 (7)	0.0656 (5)	0.835 (2)
F2A	0.6311 (4)	1.3805 (3)	0.45056 (7)	0.0799 (8)	0.835 (2)
F3A	0.9521 (3)	1.3054 (2)	0.47731 (6)	0.0656 (6)	0.835 (2)
C7B	0.6407 (12)	1.2885 (12)	0.4867 (3)	0.0462 (7)	0.165 (2)
F1B	0.4247 (12)	1.2958 (11)	0.4830 (3)	0.0656 (5)	0.165 (2)
F2B	0.7200 (17)	1.3625 (17)	0.4504 (4)	0.0799 (8)	0.165 (2)
F3B	0.7146 (16)	1.358 (3)	0.5264 (3)	0.0656 (6)	0.165 (2)
O1	0.6742 (2)	1.14194 (17)	0.48572 (4)	0.0373 (3)
O2	0.41421 (19)	0.38222 (15)	0.21250 (4)	0.0293 (3)
N1	0.6984 (2)	0.75651 (17)	0.32496 (5)	0.0257 (3)
H1	0.8076	0.7746	0.3068	0.031*
C1	0.6876 (3)	0.85474 (19)	0.36566 (6)	0.0240 (4)
C2	0.4982 (3)	0.9395 (2)	0.37426 (6)	0.0266 (4)
H2A	0.3718	0.9309	0.3530	0.032*
C3	0.4944 (3)	1.0364 (2)	0.41394 (6)	0.0284 (4)
H3A	0.3641	1.0916	0.4207	0.034*
C4	0.6822 (3)	1.0518 (2)	0.44349 (6)	0.0275 (4)
C5	0.8737 (3)	0.9724 (2)	0.43486 (6)	0.0319 (4)
H5A	1.0020	0.9859	0.4553	0.038*
C6	0.8753 (3)	0.8729 (2)	0.39589 (6)	0.0300 (4)
H6A	1.0054	0.8164	0.3897	0.036*
C8	0.5578 (3)	0.63770 (19)	0.31118 (6)	0.0223 (3)
C9A	0.3906 (7)	0.5897 (3)	0.34518 (15)	0.0240 (7)	0.835 (2)
H9AA	0.2592	0.6584	0.3402	0.029*	0.835 (2)
H9AB	0.4523	0.6060	0.3781	0.029*	0.835 (2)
C10A	0.3226 (3)	0.4141 (2)	0.33854 (7)	0.0262 (4)	0.835 (2)
H10A	0.4519	0.3455	0.3481	0.031*	0.835 (2)
C11A	0.1365 (5)	0.3730 (3)	0.37008 (10)	0.0351 (6)	0.835 (2)
H11A	0.0979	0.2603	0.3661	0.053*	0.835 (2)
H11B	0.0081	0.4390	0.3611	0.053*	0.835 (2)
H11C	0.1842	0.3934	0.4033	0.053*	0.835 (2)
C12A	0.2560 (7)	0.3828 (6)	0.28575 (9)	0.0241 (7)	0.835 (2)
H12A	0.2367	0.2667	0.2809	0.029*	0.835 (2)
H12B	0.1126	0.4345	0.2776	0.029*	0.835 (2)
C9B	0.412 (5)	0.555 (3)	0.3486 (10)	0.0240 (7)	0.165 (2)
H9BA	0.4955	0.4648	0.3638	0.029*	0.165 (2)
H9BB	0.3813	0.6322	0.3737	0.029*	0.165 (2)
C10B	0.2094 (17)	0.4962 (13)	0.3272 (4)	0.0262 (4)	0.165 (2)
H10B	0.1285	0.5830	0.3091	0.031*	0.165 (2)
C11B	0.065 (3)	0.4229 (19)	0.3647 (6)	0.0351 (6)	0.165 (2)
H11D	−0.0731	0.3842	0.3490	0.053*	0.165 (2)
H11E	0.0327	0.5043	0.3881	0.053*	0.165 (2)
H11F	0.1430	0.3340	0.3806	0.053*	0.165 (2)
C12B	0.275 (5)	0.380 (3)	0.2968 (7)	0.0241 (7)	0.165 (2)
H12C	0.1424	0.3247	0.2831	0.029*	0.165 (2)
H12D	0.3638	0.3009	0.3156	0.029*	0.165 (2)
C13	0.4186 (3)	0.4425 (2)	0.25288 (6)	0.0234 (3)
C14	0.5677 (3)	0.56830 (19)	0.26727 (5)	0.0221 (3)
C15	0.7221 (3)	0.6296 (2)	0.23177 (6)	0.0266 (4)
H15A	0.7160	0.7463	0.2309	0.040*
H15B	0.6782	0.5871	0.2003	0.040*
H15C	0.8722	0.5953	0.2411	0.040*

	U11	U22	U33	U12	U13	U23
C7A	0.067 (2)	0.0396 (13)	0.0315 (11)	0.0034 (14)	−0.0007 (13)	−0.0097 (10)
F1A	0.0878 (13)	0.0630 (11)	0.0457 (9)	0.0048 (10)	0.0030 (9)	−0.0356 (8)
F2A	0.133 (2)	0.0381 (10)	0.0634 (10)	0.0262 (13)	−0.0302 (13)	−0.0070 (8)
F3A	0.0776 (12)	0.0588 (11)	0.0630 (11)	−0.0308 (9)	0.0239 (9)	−0.0170 (9)
C7B	0.067 (2)	0.0396 (13)	0.0315 (11)	0.0034 (14)	−0.0007 (13)	−0.0097 (10)
F1B	0.0878 (13)	0.0630 (11)	0.0457 (9)	0.0048 (10)	0.0030 (9)	−0.0356 (8)
F2B	0.133 (2)	0.0381 (10)	0.0634 (10)	0.0262 (13)	−0.0302 (13)	−0.0070 (8)
F3B	0.0776 (12)	0.0588 (11)	0.0630 (11)	−0.0308 (9)	0.0239 (9)	−0.0170 (9)
O1	0.0491 (8)	0.0401 (8)	0.0232 (6)	−0.0027 (6)	0.0052 (5)	−0.0094 (5)
O2	0.0263 (6)	0.0351 (7)	0.0261 (6)	0.0009 (5)	−0.0013 (5)	−0.0081 (5)
N1	0.0273 (7)	0.0290 (7)	0.0215 (7)	−0.0044 (6)	0.0060 (5)	−0.0033 (6)
C1	0.0286 (8)	0.0242 (8)	0.0195 (7)	−0.0043 (6)	0.0033 (6)	0.0003 (6)
C2	0.0276 (8)	0.0274 (8)	0.0243 (8)	−0.0016 (7)	−0.0018 (6)	0.0003 (6)
C3	0.0291 (8)	0.0280 (8)	0.0286 (8)	0.0027 (7)	0.0039 (7)	−0.0010 (7)
C4	0.0350 (9)	0.0301 (9)	0.0177 (7)	−0.0026 (7)	0.0047 (6)	−0.0028 (6)
C5	0.0295 (9)	0.0416 (10)	0.0239 (8)	−0.0011 (8)	−0.0025 (6)	−0.0037 (7)
C6	0.0263 (8)	0.0366 (10)	0.0272 (9)	0.0019 (7)	0.0026 (6)	−0.0034 (7)
C8	0.0229 (7)	0.0214 (8)	0.0222 (8)	0.0019 (6)	−0.0002 (6)	0.0024 (6)
C9A	0.0312 (14)	0.0200 (19)	0.0214 (11)	−0.0004 (13)	0.0053 (10)	0.0006 (14)
C10A	0.0271 (10)	0.0247 (10)	0.0267 (10)	−0.0009 (7)	0.0015 (8)	0.0021 (8)
C11A	0.0386 (15)	0.0365 (15)	0.0309 (11)	−0.0095 (10)	0.0069 (11)	0.0020 (10)
C12A	0.0236 (12)	0.0291 (9)	0.0190 (18)	−0.0039 (8)	−0.0029 (13)	−0.0022 (15)
C9B	0.0312 (14)	0.0200 (19)	0.0214 (11)	−0.0004 (13)	0.0053 (10)	0.0006 (14)
C10B	0.0271 (10)	0.0247 (10)	0.0267 (10)	−0.0009 (7)	0.0015 (8)	0.0021 (8)
C11B	0.0386 (15)	0.0365 (15)	0.0309 (11)	−0.0095 (10)	0.0069 (11)	0.0020 (10)
C12B	0.0236 (12)	0.0291 (9)	0.0190 (18)	−0.0039 (8)	−0.0029 (13)	−0.0022 (15)
C13	0.0211 (7)	0.0247 (8)	0.0239 (8)	0.0058 (6)	−0.0020 (6)	−0.0013 (6)
C14	0.0222 (7)	0.0229 (8)	0.0210 (7)	0.0032 (6)	0.0003 (6)	0.0024 (6)
C15	0.0297 (8)	0.0272 (8)	0.0231 (8)	0.0004 (7)	0.0050 (6)	−0.0016 (6)

C7A—F3A	1.3189 (15)	C9A—H9AB	0.9900
C7A—F1A	1.3189 (14)	C10A—C11A	1.527 (3)
C7A—F2A	1.3195 (15)	C10A—C12A	1.543 (3)
C7A—O1	1.366 (3)	C10A—H10A	1.0000
C7B—O1	1.248 (10)	C11A—H11A	0.9800
C7B—F2B	1.3169 (16)	C11A—H11B	0.9800
C7B—F1B	1.3170 (16)	C11A—H11C	0.9800
C7B—F3B	1.3171 (16)	C12A—C13	1.489 (4)
O1—C4	1.416 (2)	C12A—H12A	0.9900
O2—C13	1.246 (2)	C12A—H12B	0.9900
N1—C8	1.356 (2)	C9B—C10B	1.43 (3)
N1—C1	1.420 (2)	C9B—H9BA	0.9900
N1—H1	0.8800	C9B—H9BB	0.9900
C1—C2	1.392 (2)	C10B—C12B	1.37 (3)
C1—C6	1.392 (2)	C10B—C11B	1.550 (18)
C2—C3	1.386 (2)	C10B—H10B	1.0000
C2—H2A	0.9500	C11B—H11D	0.9800
C3—C4	1.380 (2)	C11B—H11E	0.9800
C3—H3A	0.9500	C11B—H11F	0.9800
C4—C5	1.381 (3)	C12B—C13	1.65 (3)
C5—C6	1.382 (2)	C12B—H12C	0.9900
C5—H5A	0.9500	C12B—H12D	0.9900
C6—H6A	0.9500	C13—C14	1.436 (2)
C8—C14	1.375 (2)	C14—C15	1.510 (2)
C8—C9A	1.501 (5)	C15—H15A	0.9800
C8—C9B	1.59 (3)	C15—H15B	0.9800
C9A—C10A	1.539 (4)	C15—H15C	0.9800
C9A—H9AA	0.9900
F3A—C7A—F1A	109.09 (11)	C9A—C10A—C12A	109.5 (3)
F3A—C7A—F2A	109.02 (11)	C11A—C10A—H10A	108.4
F1A—C7A—F2A	109.13 (11)	C9A—C10A—H10A	108.4
F3A—C7A—O1	110.47 (16)	C12A—C10A—H10A	108.4
F1A—C7A—O1	105.8 (2)	C13—C12A—C10A	113.6 (3)
F2A—C7A—O1	113.21 (16)	C13—C12A—H12A	108.8
O1—C7B—F2B	112.3 (8)	C10A—C12A—H12A	108.8
O1—C7B—F1B	102.0 (7)	C13—C12A—H12B	108.8
F2B—C7B—F1B	109.45 (12)	C10A—C12A—H12B	108.8
O1—C7B—F3B	113.9 (10)	H12A—C12A—H12B	107.7
F2B—C7B—F3B	109.41 (13)	C10B—C9B—C8	112.0 (18)
F1B—C7B—F3B	109.45 (12)	C10B—C9B—H9BA	109.2
C7B—O1—C4	124.0 (4)	C8—C9B—H9BA	109.2
C7A—O1—C4	116.88 (13)	C10B—C9B—H9BB	109.2
C8—N1—C1	126.71 (14)	C8—C9B—H9BB	109.2
C8—N1—H1	116.6	H9BA—C9B—H9BB	107.9
C1—N1—H1	116.6	C12B—C10B—C9B	103.2 (17)
C2—C1—C6	119.79 (15)	C12B—C10B—C11B	110.3 (15)
C2—C1—N1	121.37 (15)	C9B—C10B—C11B	111.2 (14)
C6—C1—N1	118.73 (15)	C12B—C10B—H10B	110.6
C3—C2—C1	119.91 (15)	C9B—C10B—H10B	110.6
C3—C2—H2A	120.0	C11B—C10B—H10B	110.6
C1—C2—H2A	120.0	C10B—C11B—H11D	109.5
C4—C3—C2	119.17 (16)	C10B—C11B—H11E	109.5
C4—C3—H3A	120.4	H11D—C11B—H11E	109.5
C2—C3—H3A	120.4	C10B—C11B—H11F	109.5
C3—C4—C5	121.83 (16)	H11D—C11B—H11F	109.5
C3—C4—O1	119.18 (15)	H11E—C11B—H11F	109.5
C5—C4—O1	118.82 (16)	C10B—C12B—C13	116 (2)
C4—C5—C6	118.81 (16)	C10B—C12B—H12C	108.3
C4—C5—H5A	120.6	C13—C12B—H12C	108.3
C6—C5—H5A	120.6	C10B—C12B—H12D	108.3
C5—C6—C1	120.43 (16)	C13—C12B—H12D	108.3
C5—C6—H6A	119.8	H12C—C12B—H12D	107.4
C1—C6—H6A	119.8	O2—C13—C14	122.25 (15)
N1—C8—C14	120.43 (15)	O2—C13—C12A	117.27 (19)
N1—C8—C9A	117.2 (2)	C14—C13—C12A	120.44 (18)
C14—C8—C9A	122.3 (2)	O2—C13—C12B	125.3 (9)
N1—C8—C9B	120.2 (10)	C14—C13—C12B	112.2 (9)
C14—C8—C9B	118.3 (10)	C8—C14—C13	120.20 (15)
C8—C9A—C10A	111.6 (3)	C8—C14—C15	121.35 (15)
C8—C9A—H9AA	109.3	C13—C14—C15	118.29 (14)
C10A—C9A—H9AA	109.3	C14—C15—H15A	109.5
C8—C9A—H9AB	109.3	C14—C15—H15B	109.5
C10A—C9A—H9AB	109.3	H15A—C15—H15B	109.5
H9AA—C9A—H9AB	108.0	C14—C15—H15C	109.5
C11A—C10A—C9A	110.5 (2)	H15A—C15—H15C	109.5
C11A—C10A—C12A	111.5 (2)	H15B—C15—H15C	109.5
F2B—C7B—O1—C7A	51.0 (9)	C14—C8—C9A—C10A	29.3 (3)
F1B—C7B—O1—C7A	168.1 (11)	C9B—C8—C9A—C10A	−45 (6)
F3B—C7B—O1—C7A	−74.1 (10)	C8—C9A—C10A—C11A	−174.4 (2)
F2B—C7B—O1—C4	−32.0 (7)	C8—C9A—C10A—C12A	−51.3 (3)
F1B—C7B—O1—C4	85.1 (5)	C11A—C10A—C12A—C13	171.7 (3)
F3B—C7B—O1—C4	−157.1 (4)	C9A—C10A—C12A—C13	49.2 (4)
F3A—C7A—O1—C7B	−178.9 (9)	N1—C8—C9B—C10B	150.8 (11)
F1A—C7A—O1—C7B	63.1 (9)	C14—C8—C9B—C10B	−40.8 (17)
F2A—C7A—O1—C7B	−56.3 (9)	C9A—C8—C9B—C10B	72 (5)
F3A—C7A—O1—C4	−66.21 (18)	C8—C9B—C10B—C12B	64.6 (18)
F1A—C7A—O1—C4	175.85 (15)	C8—C9B—C10B—C11B	−177.2 (12)
F2A—C7A—O1—C4	56.4 (2)	C9B—C10B—C12B—C13	−64.6 (19)
C8—N1—C1—C2	−54.0 (2)	C11B—C10B—C12B—C13	176.6 (13)
C8—N1—C1—C6	129.73 (18)	C10A—C12A—C13—O2	158.8 (2)
C6—C1—C2—C3	−2.7 (3)	C10A—C12A—C13—C14	−23.4 (4)
N1—C1—C2—C3	−178.93 (15)	C10A—C12A—C13—C12B	16 (6)
C1—C2—C3—C4	2.4 (3)	C10B—C12B—C13—O2	−147.1 (11)
C2—C3—C4—C5	−0.5 (3)	C10B—C12B—C13—C14	37.9 (19)
C2—C3—C4—O1	−175.70 (15)	C10B—C12B—C13—C12A	−106 (7)
C7B—O1—C4—C3	−65.7 (5)	N1—C8—C14—C13	179.94 (14)
C7A—O1—C4—C3	−96.11 (19)	C9A—C8—C14—C13	−1.6 (3)
C7B—O1—C4—C5	119.0 (5)	C9B—C8—C14—C13	11.6 (10)
C7A—O1—C4—C5	88.5 (2)	N1—C8—C14—C15	−4.7 (2)
C3—C4—C5—C6	−1.1 (3)	C9A—C8—C14—C15	173.77 (17)
O1—C4—C5—C6	174.17 (16)	C9B—C8—C14—C15	−173.0 (10)
C4—C5—C6—C1	0.7 (3)	O2—C13—C14—C8	176.07 (15)
C2—C1—C6—C5	1.1 (3)	C12A—C13—C14—C8	−1.7 (3)
N1—C1—C6—C5	177.47 (16)	C12B—C13—C14—C8	−8.8 (10)
C1—N1—C8—C14	169.97 (15)	O2—C13—C14—C15	0.6 (2)
C1—N1—C8—C9A	−8.6 (3)	C12A—C13—C14—C15	−177.2 (2)
C1—N1—C8—C9B	−21.9 (10)	C12B—C13—C14—C15	175.7 (10)
N1—C8—C9A—C10A	−152.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.88	2.03	2.8538 (18)	156
C9A—H9AA···O2ii	0.99	2.58	3.428 (3)	144
C10B—H10B···O2ii	1.00	2.59	3.494 (11)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.88	2.03	2.8538 (18)	156
C9A—H9AA⋯O2ii	0.99	2.58	3.428 (3)	144
C10B—H10B⋯O2ii	1.00	2.59	3.494 (11)	150

Symmetry codes: (i) ; (ii) .