2-Amino-7,7-dimethyl-5-oxo-4-[3-(trifluoro-meth-yl)phen-yl]-1,4,5,6,7,8-hexa-hydro-quinoline-3-carbonitrile.

In the title mol-ecule, C19H18F3N3O, the dihydro-pyridine and cyclo-hexene rings both adopt sofa conformations. The five essentially planar atoms of the dihydro-pyridine ring [maximum deviation = 0.039 (2) Å] form a dihedral angle of 88.19 (8)° with the benzene ring. The F atoms of the trifluoro-methyl group were refined as disordered over two sets of sites in a 0.840 (3):0.160 (3) ratio. In the crystal, N-H⋯O and N-H⋯N hydrogen bonds link mol-ecules into a two-dimensional network parallel to (100).

Related literature

For applications of dihydro­pyridines, see: Mayler et al. (1989 ▶); Triggle et al.(1989 ▶); Leon et al. (2008 ▶). For related structures, see: Jiang et al. (2006 ▶); Tu et al. (2005 ▶). For ring conformations, see: Duax & Norton (1975 ▶).

Experimental

Crystal data

C19H18F3N3O

M = 361.36

Monoclinic,

a = 24.2434 (6) Å

b = 9.6030 (2) Å

c = 15.2426 (4) Å

β = 93.960 (2)°

V = 3540.15 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.11 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 = 0.896, T max = 1.000

42194 measured reflections

3469 independent reflections

2462 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.143

S = 1.03

3469 reflections

247 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.39 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812050684/lh5570sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050684/lh5570Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812050684/lh5570Isup3.cml

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

C19H18F3N3O	F(000) = 1504
Mr = 361.36	Dx = 1.356 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 14640 reflections
a = 24.2434 (6) Å	θ = 3.4–29.1°
b = 9.6030 (2) Å	µ = 0.11 mm−1
c = 15.2426 (4) Å	T = 293 K
β = 93.960 (2)°	Block, white
V = 3540.15 (15) Å3	0.3 × 0.2 × 0.2 mm
Z = 8

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3469 independent reflections
Radiation source: fine-focus sealed tube	2462 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.4°
ω scans	h = −29→29
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −11→11
Tmin = 0.896, Tmax = 1.000	l = −18→18
42194 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0559P)2 + 3.608P] where P = (Fo2 + 2Fc2)/3
3469 reflections	(Δ/σ)max = 0.021
247 parameters	Δρmax = 0.31 e Å−3
6 restraints	Δρmin = −0.39 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	Occ. (<1)
N1	0.08447 (8)	0.55967 (18)	1.03562 (11)	0.0401 (5)
H1	0.0954	0.5379	1.0887	0.048*
O1	0.07532 (8)	0.42797 (18)	0.73842 (10)	0.0563 (5)
C2	0.06002 (9)	0.6875 (2)	1.01957 (13)	0.0362 (5)
C3	0.04788 (9)	0.7283 (2)	0.93483 (13)	0.0354 (5)
C4	0.06809 (9)	0.6491 (2)	0.85675 (13)	0.0363 (5)
H4	0.0374	0.6442	0.8115	0.044*
C4A	0.08252 (9)	0.5025 (2)	0.88458 (13)	0.0350 (5)
C5	0.08524 (9)	0.3977 (2)	0.81668 (14)	0.0398 (5)
C6	0.09892 (10)	0.2509 (2)	0.84435 (15)	0.0456 (6)
H6A	0.1167	0.2045	0.7972	0.055*
H6B	0.0648	0.2016	0.8531	0.055*
C7	0.13683 (10)	0.2413 (2)	0.92868 (15)	0.0423 (5)
C8	0.10963 (10)	0.3241 (2)	0.99962 (14)	0.0432 (6)
H8A	0.0776	0.2732	1.0172	0.052*
H8B	0.1355	0.3325	1.0508	0.052*
C8A	0.09185 (9)	0.4663 (2)	0.96972 (13)	0.0356 (5)
C9	0.11521 (10)	0.7283 (2)	0.81799 (13)	0.0396 (5)
C10	0.16917 (10)	0.7220 (2)	0.85492 (14)	0.0430 (6)
H10	0.1778	0.6633	0.9024	0.052*
C11	0.21021 (11)	0.8024 (3)	0.82171 (16)	0.0512 (6)
C12	0.19821 (14)	0.8905 (3)	0.75167 (18)	0.0651 (8)
H12	0.2259	0.9441	0.7293	0.078*
C13	0.14494 (15)	0.8983 (3)	0.71519 (18)	0.0704 (9)
H13	0.1364	0.9585	0.6684	0.084*
C14	0.10400 (12)	0.8170 (3)	0.74772 (15)	0.0547 (7)
H14	0.0682	0.8221	0.7218	0.066*
C15	0.26709 (13)	0.7982 (4)	0.8633 (2)	0.0745 (9)
N16	0.04957 (9)	0.7592 (2)	1.09228 (12)	0.0525 (6)
H16A	0.0337	0.8392	1.0877	0.063*
H16B	0.0587	0.7251	1.1434	0.063*
C17	0.19316 (10)	0.3023 (3)	0.91246 (19)	0.0609 (7)
H17A	0.1884	0.3923	0.8855	0.091*
H17B	0.2119	0.2418	0.8742	0.091*
H17C	0.2147	0.3114	0.9674	0.091*
C18	0.14324 (13)	0.0896 (3)	0.95821 (18)	0.0643 (8)
H18A	0.1685	0.0845	1.0095	0.096*
H18B	0.1573	0.0354	0.9118	0.096*
H18C	0.1079	0.0535	0.9719	0.096*
C19	0.01978 (9)	0.8543 (2)	0.91716 (13)	0.0392 (5)
N20	−0.00412 (10)	0.9548 (2)	0.89909 (13)	0.0585 (6)
F1	0.27627 (11)	0.8904 (3)	0.92719 (19)	0.1116 (10)	0.840 (3)
F2	0.30660 (11)	0.8169 (6)	0.81017 (19)	0.168 (2)	0.840 (3)
F3	0.28039 (9)	0.6777 (3)	0.9066 (2)	0.1130 (11)	0.840 (3)
F1A	0.2709 (7)	0.782 (2)	0.9463 (6)	0.1116 (10)	0.160 (3)
F2A	0.2907 (6)	0.9202 (14)	0.8416 (11)	0.168 (2)	0.160 (3)
F3A	0.2932 (6)	0.7083 (15)	0.8168 (11)	0.1130 (11)	0.160 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0578 (12)	0.0371 (10)	0.0246 (9)	0.0141 (9)	−0.0029 (8)	−0.0001 (7)
O1	0.0772 (13)	0.0577 (11)	0.0325 (9)	0.0107 (9)	−0.0065 (8)	−0.0096 (7)
C2	0.0402 (12)	0.0354 (11)	0.0329 (11)	0.0057 (9)	0.0018 (9)	−0.0005 (9)
C3	0.0388 (12)	0.0346 (11)	0.0324 (11)	0.0072 (9)	−0.0001 (9)	−0.0006 (9)
C4	0.0385 (12)	0.0411 (12)	0.0284 (10)	0.0079 (10)	−0.0046 (9)	−0.0034 (9)
C4A	0.0347 (12)	0.0378 (12)	0.0321 (11)	0.0046 (9)	−0.0020 (9)	−0.0037 (9)
C5	0.0368 (12)	0.0460 (13)	0.0362 (12)	0.0014 (10)	−0.0010 (9)	−0.0059 (10)
C6	0.0522 (14)	0.0408 (13)	0.0438 (13)	0.0045 (11)	0.0032 (11)	−0.0109 (10)
C7	0.0482 (14)	0.0377 (12)	0.0412 (12)	0.0090 (10)	0.0053 (10)	−0.0007 (10)
C8	0.0546 (14)	0.0372 (12)	0.0379 (12)	0.0058 (11)	0.0049 (10)	0.0017 (10)
C8A	0.0365 (12)	0.0364 (11)	0.0336 (11)	0.0024 (9)	0.0008 (9)	−0.0038 (9)
C9	0.0510 (14)	0.0403 (12)	0.0276 (10)	0.0084 (10)	0.0041 (10)	−0.0023 (9)
C10	0.0489 (14)	0.0468 (13)	0.0337 (11)	0.0060 (11)	0.0049 (10)	−0.0001 (10)
C11	0.0534 (16)	0.0567 (15)	0.0450 (14)	0.0006 (12)	0.0157 (12)	−0.0084 (12)
C12	0.078 (2)	0.0660 (18)	0.0545 (16)	−0.0052 (16)	0.0301 (15)	0.0029 (14)
C13	0.096 (2)	0.072 (2)	0.0451 (16)	0.0086 (18)	0.0183 (16)	0.0219 (14)
C14	0.0634 (17)	0.0645 (17)	0.0356 (13)	0.0102 (14)	−0.0001 (12)	0.0101 (12)
C15	0.0557 (19)	0.104 (3)	0.0661 (19)	−0.0103 (18)	0.0188 (15)	−0.0020 (19)
N16	0.0822 (16)	0.0441 (11)	0.0312 (10)	0.0217 (11)	0.0048 (10)	0.0007 (9)
C17	0.0431 (15)	0.0735 (18)	0.0662 (17)	0.0134 (13)	0.0044 (12)	0.0091 (15)
C18	0.093 (2)	0.0416 (14)	0.0585 (16)	0.0215 (14)	0.0101 (15)	−0.0004 (12)
C19	0.0438 (13)	0.0441 (13)	0.0289 (11)	0.0057 (11)	−0.0034 (9)	−0.0044 (9)
N20	0.0766 (16)	0.0503 (12)	0.0466 (12)	0.0247 (12)	−0.0106 (11)	−0.0038 (10)
F1	0.1020 (19)	0.117 (2)	0.111 (2)	−0.0025 (18)	−0.0302 (15)	−0.0414 (19)
F2	0.0574 (17)	0.364 (6)	0.086 (2)	−0.026 (3)	0.0359 (14)	0.015 (3)
F3	0.0607 (15)	0.105 (2)	0.169 (3)	0.0148 (13)	−0.0228 (16)	0.017 (2)
F1A	0.1020 (19)	0.117 (2)	0.111 (2)	−0.0025 (18)	−0.0302 (15)	−0.0414 (19)
F2A	0.0574 (17)	0.364 (6)	0.086 (2)	−0.026 (3)	0.0359 (14)	0.015 (3)
F3A	0.0607 (15)	0.105 (2)	0.169 (3)	0.0148 (13)	−0.0228 (16)	0.017 (2)

N1—C8A	1.367 (3)	C10—C11	1.382 (3)
N1—C2	1.377 (3)	C10—H10	0.9300
N1—H1	0.8600	C11—C12	1.377 (4)
O1—C5	1.235 (3)	C11—C15	1.478 (4)
C2—N16	1.344 (3)	C12—C13	1.372 (4)
C2—C3	1.362 (3)	C12—H12	0.9300
C3—C19	1.406 (3)	C13—C14	1.381 (4)
C3—C4	1.522 (3)	C13—H13	0.9300
C4—C4A	1.504 (3)	C14—H14	0.9300
C4—C9	1.525 (3)	C15—F1A	1.272 (9)
C4—H4	0.9800	C15—F3A	1.308 (9)
C4A—C8A	1.348 (3)	C15—F2	1.309 (3)
C4A—C5	1.449 (3)	C15—F1	1.323 (4)
C5—C6	1.503 (3)	C15—F2A	1.355 (10)
C6—C7	1.530 (3)	C15—F3	1.360 (4)
C6—H6A	0.9700	N16—H16A	0.8600
C6—H6B	0.9700	N16—H16B	0.8600
C7—C17	1.522 (3)	C17—H17A	0.9600
C7—C8	1.528 (3)	C17—H17B	0.9600
C7—C18	1.529 (3)	C17—H17C	0.9600
C8—C8A	1.494 (3)	C18—H18A	0.9600
C8—H8A	0.9700	C18—H18B	0.9600
C8—H8B	0.9700	C18—H18C	0.9600
C9—C14	1.381 (3)	C19—N20	1.149 (3)
C9—C10	1.389 (3)
C8A—N1—C2	122.02 (17)	C11—C10—C9	120.6 (2)
C8A—N1—H1	119.0	C11—C10—H10	119.7
C2—N1—H1	119.0	C9—C10—H10	119.7
N16—C2—C3	126.42 (19)	C12—C11—C10	120.5 (3)
N16—C2—N1	114.42 (18)	C12—C11—C15	119.3 (3)
C3—C2—N1	119.14 (18)	C10—C11—C15	120.1 (2)
C2—C3—C19	119.98 (19)	C13—C12—C11	119.4 (3)
C2—C3—C4	122.51 (18)	C13—C12—H12	120.3
C19—C3—C4	117.28 (18)	C11—C12—H12	120.3
C4A—C4—C3	109.16 (17)	C12—C13—C14	120.2 (3)
C4A—C4—C9	114.22 (18)	C12—C13—H13	119.9
C3—C4—C9	110.12 (17)	C14—C13—H13	119.9
C4A—C4—H4	107.7	C9—C14—C13	121.3 (3)
C3—C4—H4	107.7	C9—C14—H14	119.4
C9—C4—H4	107.7	C13—C14—H14	119.4
C8A—C4A—C5	119.74 (19)	F1A—C15—F3A	116.9 (12)
C8A—C4A—C4	122.22 (18)	F1A—C15—F2	128.8 (8)
C5—C4A—C4	118.03 (18)	F2—C15—F1	105.7 (4)
O1—C5—C4A	120.7 (2)	F1A—C15—F2A	110.3 (11)
O1—C5—C6	121.1 (2)	F3A—C15—F2A	102.1 (10)
C4A—C5—C6	118.14 (19)	F2—C15—F3	104.9 (4)
C5—C6—C7	113.60 (18)	F1—C15—F3	101.0 (3)
C5—C6—H6A	108.8	F1A—C15—C11	115.6 (8)
C7—C6—H6A	108.8	F3A—C15—C11	104.8 (7)
C5—C6—H6B	108.8	F2—C15—C11	115.6 (3)
C7—C6—H6B	108.8	F1—C15—C11	113.7 (3)
H6A—C6—H6B	107.7	F2A—C15—C11	105.7 (8)
C17—C7—C8	110.5 (2)	F3—C15—C11	114.5 (3)
C17—C7—C18	109.9 (2)	C2—N16—H16A	120.0
C8—C7—C18	109.12 (19)	C2—N16—H16B	120.0
C17—C7—C6	109.5 (2)	H16A—N16—H16B	120.0
C8—C7—C6	107.43 (18)	C7—C17—H17A	109.5
C18—C7—C6	110.3 (2)	C7—C17—H17B	109.5
C8A—C8—C7	112.92 (18)	H17A—C17—H17B	109.5
C8A—C8—H8A	109.0	C7—C17—H17C	109.5
C7—C8—H8A	109.0	H17A—C17—H17C	109.5
C8A—C8—H8B	109.0	H17B—C17—H17C	109.5
C7—C8—H8B	109.0	C7—C18—H18A	109.5
H8A—C8—H8B	107.8	C7—C18—H18B	109.5
C4A—C8A—N1	121.11 (19)	H18A—C18—H18B	109.5
C4A—C8A—C8	123.73 (19)	C7—C18—H18C	109.5
N1—C8A—C8	115.15 (18)	H18A—C18—H18C	109.5
C14—C9—C10	118.1 (2)	H18B—C18—H18C	109.5
C14—C9—C4	119.7 (2)	N20—C19—C3	176.9 (2)
C10—C9—C4	122.06 (19)
C8A—N1—C2—N16	172.0 (2)	C2—N1—C8A—C4A	9.3 (3)
C8A—N1—C2—C3	−6.8 (3)	C2—N1—C8A—C8	−169.6 (2)
N16—C2—C3—C19	−2.7 (4)	C7—C8—C8A—C4A	21.7 (3)
N1—C2—C3—C19	176.0 (2)	C7—C8—C8A—N1	−159.39 (19)
N16—C2—C3—C4	171.7 (2)	C4A—C4—C9—C14	141.8 (2)
N1—C2—C3—C4	−9.7 (3)	C3—C4—C9—C14	−95.0 (2)
C2—C3—C4—C4A	21.0 (3)	C4A—C4—C9—C10	−42.8 (3)
C19—C3—C4—C4A	−164.59 (19)	C3—C4—C9—C10	80.4 (2)
C2—C3—C4—C9	−105.2 (2)	C14—C9—C10—C11	−0.2 (3)
C19—C3—C4—C9	69.3 (2)	C4—C9—C10—C11	−175.6 (2)
C3—C4—C4A—C8A	−18.5 (3)	C9—C10—C11—C12	0.3 (4)
C9—C4—C4A—C8A	105.2 (2)	C9—C10—C11—C15	178.0 (2)
C3—C4—C4A—C5	160.28 (18)	C10—C11—C12—C13	0.2 (4)
C9—C4—C4A—C5	−76.0 (2)	C15—C11—C12—C13	−177.5 (3)
C8A—C4A—C5—O1	178.0 (2)	C11—C12—C13—C14	−0.9 (4)
C4—C4A—C5—O1	−0.9 (3)	C10—C9—C14—C13	−0.5 (4)
C8A—C4A—C5—C6	−0.4 (3)	C4—C9—C14—C13	175.1 (2)
C4—C4A—C5—C6	−179.2 (2)	C12—C13—C14—C9	1.1 (4)
O1—C5—C6—C7	150.7 (2)	C12—C11—C15—F1A	143.6 (11)
C4A—C5—C6—C7	−31.0 (3)	C10—C11—C15—F1A	−34.2 (11)
C5—C6—C7—C17	−65.5 (3)	C12—C11—C15—F3A	−86.1 (9)
C5—C6—C7—C8	54.5 (3)	C10—C11—C15—F3A	96.1 (9)
C5—C6—C7—C18	173.4 (2)	C12—C11—C15—F2	−34.1 (5)
C17—C7—C8—C8A	70.0 (3)	C10—C11—C15—F2	148.1 (4)
C18—C7—C8—C8A	−169.0 (2)	C12—C11—C15—F1	88.4 (4)
C6—C7—C8—C8A	−49.4 (3)	C10—C11—C15—F1	−89.3 (4)
C5—C4A—C8A—N1	−173.7 (2)	C12—C11—C15—F2A	21.3 (8)
C4—C4A—C8A—N1	5.1 (3)	C10—C11—C15—F2A	−156.5 (8)
C5—C4A—C8A—C8	5.1 (3)	C12—C11—C15—F3	−156.2 (3)
C4—C4A—C8A—C8	−176.1 (2)	C10—C11—C15—F3	26.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.39	3.117 (2)	143
N16—H16A···N20ii	0.86	2.12	2.966 (3)	168
N16—H16B···O1i	0.86	2.08	2.897 (2)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.39	3.117 (2)	143
N16—H16A⋯N20ii	0.86	2.12	2.966 (3)	168
N16—H16B⋯O1i	0.86	2.08	2.897 (2)	158

Symmetry codes: (i) ; (ii) .