Ethyl 1-(2,4-dichloro­benz­yl)-4-oxo-7-trifluoro­meth­yl-1,4-dihydro­quinoline-3-carboxyl­ate

Fun, H.-K.; Ooi, C.W.; Garudachari, B.; Isloor, A.M.; Hegde, G.

doi:10.1107/S1600536812001249

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o435-o436

doi:10.1107/S1600536812001249

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Ethyl 1-(2,4-dichlorobenzyl)-4-oxo-7-trifluoromethyl-1,4-dihydroquinoline-3-carboxylate

Hoong-Kun Fun,^a ^*‡ Chin Wei Ooi,^a B. Garudachari,^b Arun M. Isloor ^b and Gurumurthy Hegde ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India, and ^cFaculty of Industrial Science and Technology, Universiti Malaysia Pahang, Lebuhraya Tun Razak, 26300 Gambang Kuantan, Pahang Darul Makmur, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 5 January 2012; accepted 11 January 2012; online 18 January 2012)

In the title compound, C₂₀H₁₄Cl₂F₃NO₃, 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 carboxylate group. In the crystal, pairs of weak C—H⋯O and C—H⋯F hydrogen bonds link molecules into centrosymmetric dimers. The crystal structure is further stabilized by weak π–π [centroid–centroid distance = 3.624 (2) Å] interactions.

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_r = 444.22
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.056
wR(F²) = 0.179
S = 1.04
5071 reflections
288 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.34 e Å⁻³

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) -x+1, -y+1, -z.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812001249/lh5400sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812001249/lh5400Isup3.cml

checkCIF report

Comment top

The quinoline moiety is of great importance to chemists as well as biologists as it is one of the key building elements for many naturally occurring compounds. Members of this family have wide range of applications as pharmaceuticals as antimalarial (Kaur et al., 2010), anti-tuberculosis (Eswaran et al., 2010), antitumor (Chou et al., 2010), anticancer (Chen et al., 2004) and antiviral (Shingalapur et al., 2009) agents. Some of the present day drugs such as chloroquine, mefloquine, tafenoquine and primaquine contain quinoline as the basic unit in their structures. In view of the biological importance, we have synthesized the title compound to study its crystal structure.

In the molecular structure (Fig. 1), the trifluromethyl group is disordered over two sets of sites in a ratio of 0.784 (10):0.216 (10). The quinoline ring (N1/C1–C9) is essentially planar with a maximum deviation of 0.058 (2) Å at atom N1. The quinoline ring makes dihedral angles of 89.23 (11) and 8.13 (17)°, respectively with the chloro-substituted benzene ring (C11–C16) and the carboxylate group (O1/O2/C17–C19). The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to a related structure (Fun et al., 2011).

In the crystal (Fig. 2), intermolecular C16—H16A···O3ⁱ and C18—H18A···F2ⁱ hydrogen bonds (Table 1) link molecules to form dimers. The crystal is further stabilized by weak π–π interactions between the quinoline (N1/C1–C9) and the benzene ring (C4–C9) [centroid-to-centroid (-x, 1 - y, -z); distance = 3.624 (2) Å].

Related literature top

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 top

A mixture of ethyl 4-hydroxy-7-(trifluoromethyl)quinoline-3-carboxylate (0.10 g, 0.00035 mol), potassium carbonate (0.053 g, 0.00038 mol) and 1-(bromomethyl)-2,4-dichlorobenzene (0.091 g, 0.00038 mol) in dimethylformamide (5 ml) was stirred at 353K for 3 h. After completion of the reaction, the reaction mixture was poured into ice-cold water. The solid product obtained was filtered, washed with water and recrystallized using ethanol. Yield: 0.150 g, 96.77%. M. p.: 428–429 K.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. Both disorder components are shown.
	Fig. 2. The crystal packing of the title compound. The dashed lines represent the hydrogen bonds. Only the major disordered component is shown.

Ethyl 1-(2,4-dichlorobenzyl)-4-oxo-7-trifluoromethyl-1,4-dihydroquinoline-3- carboxylate top

Crystal data top

C₂₀H₁₄Cl₂F₃NO₃	Z = 2
M_r = 444.22	F(000) = 452
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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 = 1.04	w = 1/[σ²(F_o²) + (0.0711P)² + 0.3522P] where P = (F_o² + 2F_c²)/3
5071 reflections	(Δ/σ)_max < 0.001
288 parameters	Δρ_max = 0.35 e Å⁻³
7 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₂₀H₁₄Cl₂F₃NO₃	γ = 67.488 (4)°
M_r = 444.22	V = 963.3 (5) Å³
Triclinic, P1	Z = 2
a = 8.090 (2) Å	Mo Kα radiation
b = 9.547 (3) Å	µ = 0.39 mm⁻¹
c = 14.047 (4) Å	T = 296 K
α = 77.299 (6)°	0.43 × 0.18 × 0.07 mm
β = 76.198 (5)°

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	5071 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2759 reflections with I > 2σ(I)
T_min = 0.852, T_max = 0.972	R_int = 0.027
13916 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	7 restraints
wR(F²) = 0.179	H-atom parameters constrained
S = 1.04	Δρ_max = 0.35 e Å⁻³
5071 reflections	Δρ_min = −0.34 e Å⁻³
288 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₄Cl₂F₃NO₃
M_r	444.22
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.090 (2), 9.547 (3), 14.047 (4)
α, β, γ (°)	77.299 (6), 76.198 (5), 67.488 (4)
V (Å³)	963.3 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.43 × 0.18 × 0.07

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.852, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	13916, 5071, 2759
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.683

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.179, 1.04
No. of reflections	5071
No. of parameters	288
No. of restraints	7
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.34

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O3ⁱ	0.9300	2.5200	3.292 (5)	141.00
C18—H18A···F2ⁱ	0.9700	2.5000	3.355 (7)	147.00

Symmetry code: (i) −x+1, −y+1, −z.

Footnotes

‡Visiting Professor, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and CWO thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). CWO also thanks the Malaysian Government and USM for the award of the post of research assistant under the Research University Grant (1001/PFIZIK/811151). AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India for the Young Scientist award.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Volume 68| Part 2| February 2012| Pages o435-o436

doi:10.1107/S1600536812001249

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 1-(2,4-di­chloro­benz­yl)-4-oxo-7-tri­fluoro­meth­yl-1,4-di­hydro­quinoline-3-carboxyl­ate

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Experimental

Crystal data

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organic compounds

Ethyl 1-(2,4-dichlorobenzyl)-4-oxo-7-trifluoromethyl-1,4-dihydroquinoline-3-carboxylate