Ethyl 1-(2,4-dichloro-benz-yl)-4-oxo-7-trifluoro-meth-yl-1,4-dihydro-quinoline-3-carboxyl-ate.

In the title compound, C(20)H(14)Cl(2)F(3)NO(3), the trifluromethyl group is disordered over two sets of sites in a 0.784 (10):0.216 (10) ratio. The quinoline ring system is essentially planar with a maximum deviation of 0.058 (2) Å for the N atom and forms dihedral angles of 89.23 (11) and 8.13 (17)°, respectively with the mean planes of the benzene ring and the carboxyl-ate group. In the crystal, pairs of weak C-H⋯O and C-H⋯F hydrogen bonds link mol-ecules into centrosymmetric dimers. The crystal structure is further stabilized by weak π-π [centroid-centroid distance = 3.624 (2) Å] inter-actions.

Related literature

For background to the properties and uses of quinoline derivatives, see: Kaur et al. (2010 ▶); Eswaran et al. (2010 ▶); Chou et al. (2010 ▶); Chen et al. (2004 ▶); Shingalapur et al. (2009 ▶). For a related structure, see: Fun et al. (2011 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C20H14Cl2F3NO3

M = 444.22

Triclinic,

a = 8.090 (2) Å

b = 9.547 (3) Å

c = 14.047 (4) Å

α = 77.299 (6)°

β = 76.198 (5)°

γ = 67.488 (4)°

V = 963.3 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.39 mm−1

T = 296 K

0.43 × 0.18 × 0.07 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.852, T max = 0.972

13916 measured reflections

5071 independent reflections

2759 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.179

S = 1.04

5071 reflections

288 parameters

7 restraints

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812001249/lh5400sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001249/lh5400Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812001249/lh5400Isup3.cml

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

C20H14Cl2F3NO3	Z = 2
Mr = 444.22	F(000) = 452
Triclinic, P1	Dx = 1.531 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.090 (2) Å	Cell parameters from 3077 reflections
b = 9.547 (3) Å	θ = 2.3–24.2°
c = 14.047 (4) Å	µ = 0.39 mm−1
α = 77.299 (6)°	T = 296 K
β = 76.198 (5)°	Block, colourless
γ = 67.488 (4)°	0.43 × 0.18 × 0.07 mm
V = 963.3 (5) Å3

Bruker APEX DUO CCD area-detector diffractometer	5071 independent reflections
Radiation source: fine-focus sealed tube	2759 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 29.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→11
Tmin = 0.852, Tmax = 0.972	k = −13→13
13916 measured reflections	l = −19→19

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0711P)2 + 0.3522P] where P = (Fo2 + 2Fc2)/3
5071 reflections	(Δ/σ)max < 0.001
288 parameters	Δρmax = 0.35 e Å−3
7 restraints	Δρmin = −0.34 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)
Cl1	−0.33323 (10)	0.73631 (10)	0.39029 (6)	0.0780 (3)
Cl2	0.24014 (16)	0.66624 (13)	0.54781 (7)	0.1052 (4)
C20	0.1448 (11)	0.0460 (8)	0.2381 (6)	0.0900 (15)	0.784 (10)
F1	0.0710 (8)	−0.0345 (4)	0.2048 (3)	0.1144 (17)	0.784 (10)
F2	0.2991 (6)	−0.0610 (5)	0.2577 (5)	0.137 (2)	0.784 (10)
F3	0.0375 (13)	0.0915 (6)	0.3154 (4)	0.197 (5)	0.784 (10)
C20A	0.134 (3)	0.055 (2)	0.2391 (13)	0.0638 (7)	0.216 (10)
F1A	0.207 (3)	−0.0777 (17)	0.2083 (14)	0.149 (7)	0.216 (10)
F2A	0.204 (2)	0.042 (2)	0.3172 (9)	0.103 (6)	0.216 (10)
F3A	−0.026 (2)	0.078 (2)	0.2781 (19)	0.149 (7)	0.216 (10)
O1	0.3593 (3)	0.7747 (2)	−0.19081 (13)	0.0747 (6)
O2	0.2188 (3)	0.9285 (2)	−0.07639 (15)	0.0818 (6)
O3	0.4032 (4)	0.4757 (3)	−0.14202 (17)	0.0992 (8)
N1	0.0638 (3)	0.5929 (2)	0.11707 (14)	0.0525 (5)
C1	0.1139 (3)	0.6989 (3)	0.04830 (18)	0.0538 (6)
H1A	0.0652	0.7997	0.0611	0.065*
C2	0.2309 (3)	0.6694 (3)	−0.03871 (18)	0.0519 (6)
C3	0.3065 (4)	0.5147 (3)	−0.0630 (2)	0.0614 (7)
C4	0.2558 (3)	0.4008 (3)	0.01455 (19)	0.0546 (6)
C5	0.3257 (4)	0.2471 (3)	−0.0008 (2)	0.0668 (7)
H5A	0.4018	0.2206	−0.0600	0.080*
C6	0.2850 (4)	0.1353 (3)	0.0693 (2)	0.0726 (8)
H6A	0.3294	0.0344	0.0570	0.087*
C7	0.1763 (4)	0.1747 (3)	0.1588 (2)	0.0638 (7)
C8	0.1019 (4)	0.3237 (3)	0.1768 (2)	0.0580 (6)
H8A	0.0275	0.3481	0.2369	0.070*
C9	0.1394 (3)	0.4388 (3)	0.10383 (18)	0.0506 (6)
C10	−0.0705 (3)	0.6443 (3)	0.20509 (18)	0.0570 (6)
H10A	−0.1461	0.5812	0.2247	0.068*
H10B	−0.1484	0.7490	0.1876	0.068*
C11	0.0122 (3)	0.6370 (3)	0.29170 (17)	0.0497 (6)
C12	−0.0999 (3)	0.6848 (3)	0.37876 (18)	0.0546 (6)
C13	−0.0312 (4)	0.6930 (3)	0.4573 (2)	0.0692 (8)
H13A	−0.1089	0.7262	0.5148	0.083*
C14	0.1529 (4)	0.6517 (3)	0.4499 (2)	0.0680 (8)
C15	0.2693 (4)	0.5999 (3)	0.3659 (2)	0.0651 (7)
H15A	0.3942	0.5695	0.3619	0.078*
C16	0.1983 (4)	0.5938 (3)	0.2878 (2)	0.0580 (6)
H16A	0.2769	0.5598	0.2307	0.070*
C17	0.2670 (3)	0.8046 (3)	−0.10207 (19)	0.0566 (6)
C18	0.3971 (5)	0.9011 (3)	−0.2582 (2)	0.0729 (8)
H18A	0.4611	0.9439	−0.2290	0.087*
H18B	0.2848	0.9811	−0.2730	0.087*
C19	0.5111 (6)	0.8397 (4)	−0.3499 (2)	0.1007 (13)
H19A	0.5278	0.9226	−0.3993	0.151*
H19B	0.4521	0.7878	−0.3740	0.151*
H19C	0.6271	0.7691	−0.3356	0.151*

	U11	U22	U33	U12	U13	U23
Cl1	0.0572 (4)	0.0910 (6)	0.0667 (5)	−0.0187 (4)	0.0125 (3)	−0.0118 (4)
Cl2	0.1179 (8)	0.1260 (8)	0.0906 (7)	−0.0464 (7)	−0.0256 (6)	−0.0378 (6)
C20	0.091 (4)	0.062 (3)	0.116 (4)	−0.028 (3)	−0.016 (3)	−0.010 (3)
F1	0.120 (4)	0.097 (2)	0.156 (3)	−0.073 (3)	−0.038 (2)	0.003 (2)
F2	0.099 (3)	0.099 (3)	0.207 (5)	−0.048 (2)	−0.072 (3)	0.069 (3)
F3	0.325 (11)	0.088 (3)	0.129 (4)	−0.094 (5)	0.092 (6)	−0.020 (3)
C20A	0.0626 (17)	0.0525 (15)	0.0778 (19)	−0.0208 (13)	−0.0151 (14)	−0.0079 (13)
F1A	0.096 (9)	0.116 (10)	0.226 (15)	−0.066 (7)	0.006 (8)	0.010 (9)
F2A	0.083 (9)	0.145 (15)	0.076 (8)	−0.057 (10)	−0.038 (7)	0.053 (8)
F3A	0.096 (9)	0.116 (10)	0.226 (15)	−0.066 (7)	0.006 (8)	0.010 (9)
O1	0.0975 (15)	0.0655 (12)	0.0540 (11)	−0.0334 (11)	0.0120 (10)	−0.0122 (9)
O2	0.1094 (17)	0.0645 (13)	0.0696 (13)	−0.0377 (12)	0.0106 (12)	−0.0200 (10)
O3	0.1143 (19)	0.0721 (14)	0.0803 (15)	−0.0225 (13)	0.0394 (13)	−0.0285 (12)
N1	0.0536 (12)	0.0498 (11)	0.0481 (11)	−0.0138 (9)	0.0006 (9)	−0.0124 (9)
C1	0.0558 (15)	0.0509 (14)	0.0526 (14)	−0.0154 (11)	−0.0049 (11)	−0.0139 (11)
C2	0.0520 (14)	0.0529 (14)	0.0486 (13)	−0.0178 (11)	−0.0027 (11)	−0.0103 (11)
C3	0.0539 (15)	0.0601 (16)	0.0569 (15)	−0.0089 (12)	0.0025 (12)	−0.0153 (12)
C4	0.0477 (13)	0.0523 (14)	0.0582 (15)	−0.0091 (11)	−0.0061 (11)	−0.0153 (11)
C5	0.0615 (17)	0.0576 (16)	0.0692 (18)	−0.0067 (13)	−0.0025 (13)	−0.0198 (14)
C6	0.0751 (19)	0.0515 (16)	0.087 (2)	−0.0132 (14)	−0.0137 (16)	−0.0176 (15)
C7	0.0626 (17)	0.0525 (15)	0.0778 (19)	−0.0208 (13)	−0.0151 (14)	−0.0079 (13)
C8	0.0548 (15)	0.0585 (16)	0.0601 (15)	−0.0212 (12)	−0.0063 (12)	−0.0087 (12)
C9	0.0476 (13)	0.0481 (13)	0.0553 (14)	−0.0139 (11)	−0.0070 (11)	−0.0131 (11)
C10	0.0511 (14)	0.0554 (14)	0.0551 (15)	−0.0129 (11)	0.0065 (11)	−0.0168 (12)
C11	0.0544 (14)	0.0411 (12)	0.0491 (13)	−0.0184 (10)	0.0034 (10)	−0.0076 (10)
C12	0.0558 (14)	0.0498 (14)	0.0491 (14)	−0.0196 (11)	0.0069 (11)	−0.0039 (11)
C13	0.078 (2)	0.0700 (18)	0.0518 (16)	−0.0258 (15)	0.0095 (14)	−0.0156 (13)
C14	0.081 (2)	0.0682 (18)	0.0591 (16)	−0.0310 (16)	−0.0091 (15)	−0.0132 (14)
C15	0.0621 (17)	0.0616 (17)	0.0757 (19)	−0.0261 (14)	−0.0078 (14)	−0.0140 (14)
C16	0.0562 (15)	0.0569 (15)	0.0578 (15)	−0.0208 (12)	0.0045 (12)	−0.0156 (12)
C17	0.0541 (15)	0.0618 (16)	0.0529 (14)	−0.0210 (12)	−0.0026 (11)	−0.0119 (12)
C18	0.084 (2)	0.0724 (19)	0.0620 (17)	−0.0388 (16)	0.0061 (15)	−0.0073 (14)
C19	0.137 (3)	0.100 (3)	0.064 (2)	−0.058 (3)	0.023 (2)	−0.0218 (18)

Cl1—C12	1.735 (3)	C5—H5A	0.9300
Cl2—C14	1.741 (3)	C6—C7	1.388 (4)
C20—F3	1.262 (8)	C6—H6A	0.9300
C20—F2	1.320 (7)	C7—C8	1.371 (4)
C20—F1	1.344 (8)	C8—C9	1.401 (4)
C20—C7	1.522 (8)	C8—H8A	0.9300
C20A—F3A	1.235 (16)	C10—C11	1.499 (4)
C20A—F1A	1.303 (16)	C10—H10A	0.9700
C20A—F2A	1.311 (16)	C10—H10B	0.9700
C20A—C7	1.494 (17)	C11—C12	1.387 (3)
O1—C17	1.320 (3)	C11—C16	1.391 (4)
O1—C18	1.445 (3)	C12—C13	1.377 (4)
O2—C17	1.204 (3)	C13—C14	1.371 (4)
O3—C3	1.236 (3)	C13—H13A	0.9300
N1—C1	1.349 (3)	C14—C15	1.376 (4)
N1—C9	1.396 (3)	C15—C16	1.375 (4)
N1—C10	1.472 (3)	C15—H15A	0.9300
C1—C2	1.365 (3)	C16—H16A	0.9300
C1—H1A	0.9300	C18—C19	1.485 (4)
C2—C3	1.450 (4)	C18—H18A	0.9700
C2—C17	1.484 (4)	C18—H18B	0.9700
C3—C4	1.465 (4)	C19—H19A	0.9600
C4—C5	1.401 (4)	C19—H19B	0.9600
C4—C9	1.402 (3)	C19—H19C	0.9600
C5—C6	1.367 (4)
F3—C20—F2	112.3 (8)	N1—C9—C8	121.8 (2)
F3—C20—F1	105.5 (6)	N1—C9—C4	118.2 (2)
F2—C20—F1	101.2 (6)	C8—C9—C4	120.1 (2)
F3—C20—C7	113.9 (6)	N1—C10—C11	113.9 (2)
F2—C20—C7	111.8 (6)	N1—C10—H10A	108.8
F1—C20—C7	111.2 (6)	C11—C10—H10A	108.8
F3A—C20A—F1A	110.4 (17)	N1—C10—H10B	108.8
F3A—C20A—F2A	99.9 (16)	C11—C10—H10B	108.8
F1A—C20A—F2A	106.3 (18)	H10A—C10—H10B	107.7
F3A—C20A—C7	118.3 (17)	C12—C11—C16	117.1 (2)
F1A—C20A—C7	109.6 (14)	C12—C11—C10	119.6 (2)
F2A—C20A—C7	111.4 (13)	C16—C11—C10	123.2 (2)
C17—O1—C18	116.3 (2)	C13—C12—C11	121.8 (3)
C1—N1—C9	120.0 (2)	C13—C12—Cl1	118.4 (2)
C1—N1—C10	118.3 (2)	C11—C12—Cl1	119.8 (2)
C9—N1—C10	121.7 (2)	C14—C13—C12	119.3 (3)
N1—C1—C2	124.9 (2)	C14—C13—H13A	120.3
N1—C1—H1A	117.6	C12—C13—H13A	120.3
C2—C1—H1A	117.6	C13—C14—C15	120.8 (3)
C1—C2—C3	119.4 (2)	C13—C14—Cl2	119.5 (2)
C1—C2—C17	115.1 (2)	C15—C14—Cl2	119.7 (3)
C3—C2—C17	125.5 (2)	C16—C15—C14	119.1 (3)
O3—C3—C2	125.5 (3)	C16—C15—H15A	120.4
O3—C3—C4	120.0 (2)	C14—C15—H15A	120.4
C2—C3—C4	114.5 (2)	C15—C16—C11	121.8 (2)
C5—C4—C9	118.3 (2)	C15—C16—H16A	119.1
C5—C4—C3	118.9 (2)	C11—C16—H16A	119.1
C9—C4—C3	122.8 (2)	O2—C17—O1	122.9 (2)
C6—C5—C4	121.6 (3)	O2—C17—C2	124.4 (2)
C6—C5—H5A	119.2	O1—C17—C2	112.6 (2)
C4—C5—H5A	119.2	O1—C18—C19	107.1 (3)
C5—C6—C7	119.0 (3)	O1—C18—H18A	110.3
C5—C6—H6A	120.5	C19—C18—H18A	110.3
C7—C6—H6A	120.5	O1—C18—H18B	110.3
C8—C7—C6	121.6 (3)	C19—C18—H18B	110.3
C8—C7—C20A	117.5 (8)	H18A—C18—H18B	108.6
C6—C7—C20A	120.9 (8)	C18—C19—H19A	109.5
C8—C7—C20	120.7 (4)	C18—C19—H19B	109.5
C6—C7—C20	117.7 (4)	H19A—C19—H19B	109.5
C7—C8—C9	119.3 (3)	C18—C19—H19C	109.5
C7—C8—H8A	120.4	H19A—C19—H19C	109.5
C9—C8—H8A	120.4	H19B—C19—H19C	109.5
C9—N1—C1—C2	3.1 (4)	C20A—C7—C8—C9	179.4 (8)
C10—N1—C1—C2	−177.2 (2)	C20—C7—C8—C9	177.5 (4)
N1—C1—C2—C3	1.6 (4)	C1—N1—C9—C8	174.9 (2)
N1—C1—C2—C17	−179.3 (2)	C10—N1—C9—C8	−4.8 (4)
C1—C2—C3—O3	174.7 (3)	C1—N1—C9—C4	−5.0 (4)
C17—C2—C3—O3	−4.3 (5)	C10—N1—C9—C4	175.2 (2)
C1—C2—C3—C4	−3.8 (4)	C7—C8—C9—N1	178.3 (2)
C17—C2—C3—C4	177.2 (2)	C7—C8—C9—C4	−1.7 (4)
O3—C3—C4—C5	3.0 (4)	C5—C4—C9—N1	−177.3 (2)
C2—C3—C4—C5	−178.4 (3)	C3—C4—C9—N1	2.6 (4)
O3—C3—C4—C9	−176.8 (3)	C5—C4—C9—C8	2.7 (4)
C2—C3—C4—C9	1.8 (4)	C3—C4—C9—C8	−177.4 (2)
C9—C4—C5—C6	−0.8 (4)	C1—N1—C10—C11	−93.1 (3)
C3—C4—C5—C6	179.3 (3)	C9—N1—C10—C11	86.7 (3)
C4—C5—C6—C7	−2.1 (5)	N1—C10—C11—C12	178.9 (2)
C5—C6—C7—C8	3.2 (5)	N1—C10—C11—C16	3.4 (3)
C5—C6—C7—C20A	−177.6 (8)	C16—C11—C12—C13	1.6 (4)
C5—C6—C7—C20	−175.6 (4)	C10—C11—C12—C13	−174.2 (2)
F3A—C20A—C7—C8	49 (2)	C16—C11—C12—Cl1	−178.55 (18)
F1A—C20A—C7—C8	176.8 (13)	C10—C11—C12—Cl1	5.6 (3)
F2A—C20A—C7—C8	−65.8 (19)	C11—C12—C13—C14	−0.6 (4)
F3A—C20A—C7—C6	−130.1 (17)	Cl1—C12—C13—C14	179.5 (2)
F1A—C20A—C7—C6	−2.5 (18)	C12—C13—C14—C15	−1.1 (4)
F2A—C20A—C7—C6	114.9 (15)	C12—C13—C14—Cl2	178.5 (2)
F3A—C20A—C7—C20	−159 (16)	C13—C14—C15—C16	1.7 (4)
F1A—C20A—C7—C20	−31 (14)	Cl2—C14—C15—C16	−177.9 (2)
F2A—C20A—C7—C20	86 (15)	C14—C15—C16—C11	−0.7 (4)
F3—C20—C7—C8	4.5 (8)	C12—C11—C16—C15	−0.9 (4)
F2—C20—C7—C8	−124.1 (6)	C10—C11—C16—C15	174.7 (2)
F1—C20—C7—C8	123.6 (6)	C18—O1—C17—O2	−1.4 (4)
F3—C20—C7—C6	−176.7 (6)	C18—O1—C17—C2	178.7 (2)
F2—C20—C7—C6	54.7 (8)	C1—C2—C17—O2	9.3 (4)
F1—C20—C7—C6	−57.6 (8)	C3—C2—C17—O2	−171.8 (3)
F3—C20—C7—C20A	−24 (14)	C1—C2—C17—O1	−170.9 (2)
F2—C20—C7—C20A	−153 (15)	C3—C2—C17—O1	8.1 (4)
F1—C20—C7—C20A	95 (15)	C17—O1—C18—C19	176.4 (3)
C6—C7—C8—C9	−1.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O3i	0.93	2.52	3.292 (5)	141
C18—H18A···F2i	0.97	2.50	3.355 (7)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O3i	0.93	2.52	3.292 (5)	141
C18—H18A⋯F2i	0.97	2.50	3.355 (7)	147

Symmetry code: (i) .