7-Amino-4-hy-droxy-4-trifluoro-methyl-3,4-dihydro-quinolin-2(1H)-one.

The title compound, C(10)H(9)F(3)N(2)O(2), was prepared by the reaction of m-phenyl-enediamine and ethyl 4,4,4-trifluoro-acetoacetate. In the crystal, inter-molecular C-H⋯ F, N-H⋯F, O-H⋯N and N-H⋯O inter-actions contribute to the crystal packing.

Related literature

For general background to quinolino­nes, see: Chilin et al. (1991 ▶); Oeveren et al. (2006 ▶). For related structures, see: Oeveren et al. (2007 ▶). For ring conformation analysis, see Cremer & Pople (1975 ▶).

Experimental

Crystal data

C10H9F3N2O2

M = 246.19

Monoclinic,

a = 8.6770 (9) Å

b = 10.0816 (11) Å

c = 11.6293 (12) Å

β = 95.747 (2)°

V = 1012.20 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.15 mm−1

T = 296 K

0.20 × 0.18 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.971, T max = 0.978

6400 measured reflections

2283 independent reflections

2021 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.112

S = 1.06

2283 reflections

170 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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 datablock(s) I, global. DOI: 10.1107/S1600536811035471/mw2019sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035471/mw2019Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035471/mw2019Isup3.cml

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

C10H9F3N2O2	F(000) = 504
Mr = 246.19	Dx = 1.616 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4544 reflections
a = 8.6770 (9) Å	θ = 2.4–30.4°
b = 10.0816 (11) Å	µ = 0.15 mm−1
c = 11.6293 (12) Å	T = 296 K
β = 95.747 (2)°	Prism, yellow
V = 1012.20 (18) Å3	0.20 × 0.18 × 0.15 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2283 independent reflections
Radiation source: fine-focus sealed tube	2021 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→10
Tmin = 0.971, Tmax = 0.978	k = −12→8
6400 measured reflections	l = −15→15

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0568P)2 + 0.3518P] where P = (Fo2 + 2Fc2)/3
2283 reflections	(Δ/σ)max < 0.001
170 parameters	Δρmax = 0.33 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 > 2sigma(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	0.12400 (17)	0.21289 (16)	0.23013 (12)	0.0372 (3)
C2	0.19252 (14)	0.08079 (13)	0.27561 (10)	0.0268 (3)
C3	0.35833 (14)	0.10123 (13)	0.32715 (10)	0.0258 (3)
C4	0.39150 (15)	0.15288 (14)	0.43763 (11)	0.0313 (3)
H4	0.3104	0.1748	0.4807	0.038*
C5	0.54182 (16)	0.17229 (14)	0.48484 (11)	0.0316 (3)
H5	0.5613	0.2075	0.5588	0.038*
C6	0.66507 (14)	0.13917 (13)	0.42169 (11)	0.0272 (3)
C7	0.63442 (14)	0.08873 (14)	0.31075 (10)	0.0280 (3)
H7	0.7158	0.0669	0.2679	0.034*
C8	0.48175 (14)	0.07080 (13)	0.26335 (10)	0.0254 (3)
C9	0.31363 (15)	−0.01002 (14)	0.09840 (11)	0.0292 (3)
C10	0.18645 (15)	−0.02086 (15)	0.17766 (12)	0.0340 (3)
H10A	0.1903	−0.1089	0.2114	0.041*
H10B	0.0875	−0.0122	0.1314	0.041*
F1	0.13125 (13)	0.30710 (10)	0.31014 (9)	0.0552 (3)
F2	0.19747 (15)	0.25830 (12)	0.14294 (10)	0.0652 (4)
F3	−0.02624 (11)	0.20090 (12)	0.19086 (9)	0.0572 (3)
N1	0.81794 (14)	0.15133 (14)	0.47467 (11)	0.0333 (3)
N2	0.45399 (13)	0.02567 (12)	0.14878 (9)	0.0309 (3)
O1	0.09075 (11)	0.04442 (11)	0.35806 (8)	0.0334 (3)
O2	0.29139 (12)	−0.03941 (11)	−0.00459 (8)	0.0377 (3)
H1B	0.532 (2)	0.026 (2)	0.1011 (16)	0.048 (5)*
H1A	0.893 (3)	0.136 (2)	0.4276 (17)	0.053 (5)*
H2A	0.833 (2)	0.225 (2)	0.5140 (17)	0.049 (5)*
H1C	0.129 (2)	−0.013 (2)	0.4017 (17)	0.052 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0338 (7)	0.0466 (8)	0.0327 (7)	0.0068 (6)	0.0103 (6)	0.0097 (6)
C2	0.0231 (6)	0.0364 (7)	0.0223 (5)	0.0016 (5)	0.0089 (4)	0.0026 (5)
C3	0.0233 (6)	0.0314 (6)	0.0238 (6)	0.0016 (5)	0.0075 (4)	−0.0006 (5)
C4	0.0293 (6)	0.0400 (7)	0.0261 (6)	0.0047 (5)	0.0104 (5)	−0.0051 (5)
C5	0.0336 (7)	0.0381 (7)	0.0236 (6)	0.0006 (5)	0.0056 (5)	−0.0068 (5)
C6	0.0257 (6)	0.0291 (6)	0.0270 (6)	−0.0004 (5)	0.0041 (5)	0.0017 (5)
C7	0.0247 (6)	0.0346 (7)	0.0263 (6)	0.0008 (5)	0.0098 (5)	−0.0016 (5)
C8	0.0266 (6)	0.0287 (6)	0.0220 (6)	0.0002 (5)	0.0082 (4)	−0.0017 (5)
C9	0.0301 (6)	0.0326 (7)	0.0259 (6)	−0.0018 (5)	0.0078 (5)	−0.0039 (5)
C10	0.0277 (6)	0.0437 (8)	0.0316 (7)	−0.0082 (5)	0.0086 (5)	−0.0051 (6)
F1	0.0573 (6)	0.0454 (6)	0.0630 (7)	0.0190 (5)	0.0057 (5)	−0.0057 (5)
F2	0.0781 (8)	0.0630 (7)	0.0605 (7)	0.0136 (6)	0.0360 (6)	0.0336 (6)
F3	0.0394 (5)	0.0721 (7)	0.0575 (6)	0.0128 (5)	−0.0082 (4)	0.0183 (5)
N1	0.0269 (6)	0.0430 (7)	0.0301 (6)	−0.0026 (5)	0.0028 (5)	−0.0002 (5)
N2	0.0270 (5)	0.0439 (7)	0.0235 (5)	−0.0030 (5)	0.0103 (4)	−0.0072 (5)
O1	0.0246 (5)	0.0497 (6)	0.0278 (5)	0.0051 (4)	0.0116 (4)	0.0112 (4)
O2	0.0361 (5)	0.0519 (6)	0.0257 (5)	−0.0045 (4)	0.0057 (4)	−0.0085 (4)

C1—F1	1.3267 (19)	C6—N1	1.4109 (17)
C1—F2	1.3318 (17)	C7—C8	1.3947 (17)
C1—F3	1.3429 (18)	C7—H7	0.9300
C1—C2	1.531 (2)	C8—N2	1.4057 (16)
C2—O1	1.4153 (14)	C9—O2	1.2301 (16)
C2—C3	1.5162 (17)	C9—N2	1.3465 (17)
C2—C10	1.5292 (18)	C9—C10	1.5110 (17)
C3—C4	1.3896 (17)	C10—H10A	0.9700
C3—C8	1.3966 (16)	C10—H10B	0.9700
C4—C5	1.3776 (19)	N1—H1A	0.91 (2)
C4—H4	0.9300	N1—H2A	0.87 (2)
C5—C6	1.3970 (17)	N2—H1B	0.92 (2)
C5—H5	0.9300	O1—H1C	0.82 (2)
C6—C7	1.3875 (18)
F1—C1—F2	107.17 (14)	C5—C6—N1	119.03 (12)
F1—C1—F3	106.21 (12)	C6—C7—C8	120.07 (11)
F2—C1—F3	107.12 (12)	C6—C7—H7	120.0
F1—C1—C2	113.02 (12)	C8—C7—H7	120.0
F2—C1—C2	111.29 (12)	C7—C8—C3	120.67 (11)
F3—C1—C2	111.68 (13)	C7—C8—N2	118.84 (10)
O1—C2—C3	113.53 (10)	C3—C8—N2	120.46 (11)
O1—C2—C10	110.72 (11)	O2—C9—N2	122.34 (12)
C3—C2—C10	110.25 (10)	O2—C9—C10	121.57 (12)
O1—C2—C1	102.26 (10)	N2—C9—C10	115.97 (11)
C3—C2—C1	109.79 (11)	C9—C10—C2	115.66 (11)
C10—C2—C1	110.02 (11)	C9—C10—H10A	108.4
C4—C3—C8	118.34 (12)	C2—C10—H10A	108.4
C4—C3—C2	121.13 (11)	C9—C10—H10B	108.4
C8—C3—C2	120.52 (11)	C2—C10—H10B	108.4
C5—C4—C3	121.46 (11)	H10A—C10—H10B	107.4
C5—C4—H4	119.3	C6—N1—H1A	115.2 (13)
C3—C4—H4	119.3	C6—N1—H2A	112.7 (13)
C4—C5—C6	120.04 (12)	H1A—N1—H2A	112.4 (18)
C4—C5—H5	120.0	C9—N2—C8	124.10 (11)
C6—C5—H5	120.0	C9—N2—H1B	115.3 (12)
C7—C6—C5	119.40 (11)	C8—N2—H1B	120.3 (12)
C7—C6—N1	121.48 (11)	C2—O1—H1C	111.2 (14)
F1—C1—C2—O1	64.75 (14)	C4—C5—C6—N1	−175.69 (13)
F2—C1—C2—O1	−174.61 (13)	C5—C6—C7—C8	−0.3 (2)
F3—C1—C2—O1	−54.94 (14)	N1—C6—C7—C8	176.28 (12)
F1—C1—C2—C3	−56.07 (14)	C6—C7—C8—C3	−1.0 (2)
F2—C1—C2—C3	64.58 (15)	C6—C7—C8—N2	176.92 (12)
F3—C1—C2—C3	−175.76 (11)	C4—C3—C8—C7	1.62 (19)
F1—C1—C2—C10	−177.58 (11)	C2—C3—C8—C7	−179.61 (12)
F2—C1—C2—C10	−56.93 (16)	C4—C3—C8—N2	−176.26 (12)
F3—C1—C2—C10	62.73 (14)	C2—C3—C8—N2	2.50 (19)
O1—C2—C3—C4	−34.07 (17)	O2—C9—C10—C2	−147.86 (14)
C10—C2—C3—C4	−158.94 (12)	N2—C9—C10—C2	36.06 (18)
C1—C2—C3—C4	79.68 (15)	O1—C2—C10—C9	−167.21 (11)
O1—C2—C3—C8	147.20 (12)	C3—C2—C10—C9	−40.75 (16)
C10—C2—C3—C8	22.32 (16)	C1—C2—C10—C9	80.49 (15)
C1—C2—C3—C8	−99.05 (14)	O2—C9—N2—C8	174.33 (13)
C8—C3—C4—C5	−0.9 (2)	C10—C9—N2—C8	−9.6 (2)
C2—C3—C4—C5	−179.71 (13)	C7—C8—N2—C9	171.88 (13)
C3—C4—C5—C6	−0.4 (2)	C3—C8—N2—C9	−10.2 (2)
C4—C5—C6—C7	1.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.91 (2)	2.17 (2)	3.0409 (16)	160.0 (18)
N2—H1B···O2ii	0.92 (2)	1.99 (2)	2.9075 (15)	175.3 (18)
O1—H1C···N1iii	0.82 (2)	2.02 (2)	2.8280 (16)	168 (2)
N1—H2A···F3iv	0.87 (2)	2.41 (2)	3.1124 (16)	138.5 (17)
C4—H4···F2v	0.93	2.31	3.1846 (16)	156.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.91 (2)	2.17 (2)	3.0409 (16)	160.0 (18)
N2—H1B⋯O2ii	0.92 (2)	1.99 (2)	2.9075 (15)	175.3 (18)
O1—H1C⋯N1iii	0.82 (2)	2.02 (2)	2.8280 (16)	168 (2)
N1—H2A⋯F3iv	0.87 (2)	2.41 (2)	3.1124 (16)	138.5 (17)
C4—H4⋯F2v	0.93	2.31	3.1846 (16)	156

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .