Ethyl 3-(2-eth­oxy-2-oxoeth­oxy)-6-(tri­fluoro­meth­yl)furo[3,2-c]quinoline-2-carboxyl­ate

Garudachari, B.; Islor, A.M.; Vijesh, A.M.; Gerber, T.; Hosten, E.; Betz, R.

doi:10.1107/S1600536812046843

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages o3389-o3390

doi:10.1107/S1600536812046843

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Ethyl 3-(2-ethoxy-2-oxoethoxy)-6-(trifluoromethyl)furo[3,2-c]quinoline-2-carboxylate

B. Garudachari,^a Arun M. Islor,^a A. M. Vijesh,^b Thomas Gerber,^c Eric Hosten ^c and Richard Betz ^c ^*

^aNational Institute of Technology-Karnataka, Department of Chemistry, Medicinal Chemistry Laboratory, Surathkal, Mangalore 575 025, India, ^bGITAM University, Department of Engineering Chemistry, GIT, Rushikonda, Visakhapatnam, A.P. 530 045, India, and ^cNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
^*Correspondence e-mail: richard.betz@webmail.co.za

(Received 31 October 2012; accepted 14 November 2012; online 24 November 2012)

In the title compound, C₁₉H₁₆F₃NO₆, a quinoline derivative featuring an annealated furan substituent, the mean planes of the carboxy substituents are at an angle of 74.3 (2)°. In the crystal, C—H⋯O contacts result in undulating chains along [110]. C—H⋯F contacts also occur. The shortest centroid–centroid distance between rings is 3.3376 (7) Å, involving two furan rings of neighbouring molecules.

Related literature

For background to the pharmacological activity of heterocyclic compounds, see: Isloor et al. (2000 , 2009 ); Caprio et al. (2000 ); Kaur et al. (2010 ); Chou et al. (2010 ); Chen et al. (2004 ); Garudachari et al. (2012 ); Shingalapur et al. (2009 ). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ); Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₉H₁₆F₃NO₆
M_r = 411.33
Triclinic, $[P \overline 1]$
a = 8.9167 (3) Å
b = 8.9223 (3) Å
c = 13.4125 (5) Å
α = 102.895 (1)°
β = 97.098 (2)°
γ = 116.035 (1)°
V = 904.22 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 200 K
0.56 × 0.38 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.918, T_max = 0.980
19743 measured reflections
4499 independent reflections
4019 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.096
S = 1.04
4499 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O3ⁱ	0.95	2.44	3.2556 (13)	144
C13—H13B⋯F1ⁱⁱ	0.99	2.46	3.2829 (12)	141
Symmetry codes: (i) -x, -y, -z; (ii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2010 ); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; 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 Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812046843/fj2605sup1.cif

Supporting information file. DOI: 10.1107/S1600536812046843/fj2605Isup2.cdx

Structure factors: contains datablock I. DOI: 10.1107/S1600536812046843/fj2605Isup3.hkl

Supporting information file. DOI: 10.1107/S1600536812046843/fj2605Isup4.cml

checkCIF report

Comment top

Heterocyclic compounds play an important role in our ongoing interest in developing new antimicrobial agents (Isloor et al., 2000; Isloor et al., 2009). The quinoline nucleus is one of the most important and widely exploited heterocyclic ring systems for the development of bioactive molecules (Caprio et al., 2000). Members of this family have a wide range of applications in pharmacology as antimalarial (Kaur et al., 2010), antitumor (Chou et al., 2010), anticancer (Chen et al., 2004), antimicrobial (Garudachari et al., 2012) and antiviral (Shingalapur et al., 2009) agents. In view of the promising biological and pharmaceutical activity, the title compound was synthesized to study its crystal structure.

The aromatic scaffold is essentially flat. The least-squares plane defined by all the non-hydrogen atoms (r.m.s. of all fitted atoms = 0.0175 Å) features the carbon atom bearing the trifluoromethyl group as the atom deviating most from this common plane by 0.029 (1) Å. The least-squares planes defined by the respective atoms of the phenyl moiety and the furane moiety intersect at an angle of 2.26 (6) ° while they enclose angles of 0.76 (5) ° and 1.51 (6) ° with the least-squares plane defined by the atoms of the central heterocycle. The fluorine atoms of the trifluoromethyl group adopt a staggered conformation with respect to the nitrogen atom. The two carboxy substituents bonded to the furane system are orientated nearly perpendicular to each other with the least-squares planes defined by their respective atoms enclosing an angle of 74.3 (2) °. (Fig. 1).

In the crystal, C–H···O and C–H···F contacts are apparent whose range invariably falls by more than 0.2 Å below the sum of van-der-Waals radii of the atoms participating. While the former contacts are supported by the hydrogen atom in ortho position to the trifluoromethyl group as the donor and one of the double bonded oxygen atoms as the acceptor, the C–H···F contacts stem from one of the hydrogen atoms of a methylene group. Metrical parameters as well as information about the symmetry of these contacts are summarized in Table 1. In total, the molecules are connected to undulated chains along [1 1 0]. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for these contacts is R²₂(22)R²₂(24) on the unary level. The shortest intercentroid distance between two aromatic systems was measured at 3.3376 (7) Å and is apparent between two furane moieties in neighbouring molecules (Fig. 2).

Related literature top

For background to the pharmacological activity of heterocyclic compounds, see: Isloor et al. (2000, 2009); Caprio et al. (2000); Kaur et al. (2010); Chou et al. (2010); Chen et al. (2004); Garudachari et al. (2012); Shingalapur et al. (2009). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental top

To a suspension of ethyl 4-hydroxy-8-(trifluoromethyl)quinoline-3-carboxylate (1.0 g, 0.0035 mol) and potassium carbonate (1.06 g, 0.0077 mol) in dimethylformamide (10 ml) ethyl 4-chloroacetoacetate (0.943 g, 0.0077 mol) was added. The mixture was allowed to stir at 80 °C for 2 h and was then quenched by the slow addition of water (25 ml). The precipitated solids were collected by filtration and recrystallized from ethanol, yield: 1.20 g (83.33%).

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); 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 Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level).
	Fig. 2. Intermolecular contacts, viewed along [0 1 0]. For clarity, only the C–H···F contacts are depicted. Symmetry operator: ⁱ -x + 1, -y + 1, -z.

Ethyl 3-(2-ethoxy-2-oxoethoxy)-6-(trifluoromethyl)furo[3,2-c]quinoline- 2-carboxylate top

Crystal data top

C₁₉H₁₆F₃NO₆	Z = 2
M_r = 411.33	F(000) = 424
Triclinic, P1	D_x = 1.511 Mg m⁻³
Hall symbol: -P 1	Melting point = 400–398 K
a = 8.9167 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9223 (3) Å	Cell parameters from 9936 reflections
c = 13.4125 (5) Å	θ = 2.7–28.5°
α = 102.895 (1)°	µ = 0.13 mm⁻¹
β = 97.098 (2)°	T = 200 K
γ = 116.035 (1)°	Block, colourless
V = 904.22 (5) Å³	0.56 × 0.38 × 0.15 mm

Data collection top

Bruker APEXII CCD diffractometer	4499 independent reflections
Radiation source: fine-focus sealed tube	4019 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
ϕ and ω scans	θ_max = 28.5°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
T_min = 0.918, T_max = 0.980	k = −10→11
19743 measured reflections	l = −17→17

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0475P)² + 0.2384P] where P = (F_o² + 2F_c²)/3
4499 reflections	(Δ/σ)_max < 0.001
264 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₉H₁₆F₃NO₆	γ = 116.035 (1)°
M_r = 411.33	V = 904.22 (5) Å³
Triclinic, P1	Z = 2
a = 8.9167 (3) Å	Mo Kα radiation
b = 8.9223 (3) Å	µ = 0.13 mm⁻¹
c = 13.4125 (5) Å	T = 200 K
α = 102.895 (1)°	0.56 × 0.38 × 0.15 mm
β = 97.098 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4499 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4019 reflections with I > 2σ(I)
T_min = 0.918, T_max = 0.980	R_int = 0.014
19743 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.04	Δρ_max = 0.33 e Å⁻³
4499 reflections	Δρ_min = −0.21 e Å⁻³
264 parameters

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

	x	y	z	U_iso*/U_eq
F1	0.11127 (9)	−0.15513 (9)	−0.26381 (6)	0.04187 (17)
F2	−0.02108 (11)	−0.07488 (11)	−0.36753 (6)	0.04779 (19)
F3	−0.14712 (10)	−0.33572 (10)	−0.35590 (6)	0.0530 (2)
O1	−0.01551 (9)	0.36022 (10)	0.09774 (6)	0.02896 (16)
O2	0.39515 (10)	0.69558 (10)	0.08994 (6)	0.03272 (17)
O3	0.52925 (10)	0.64136 (10)	0.26519 (6)	0.03546 (18)
O4	0.61251 (10)	0.91813 (10)	0.36366 (6)	0.03402 (17)
O5	0.21017 (12)	0.77916 (13)	0.29209 (8)	0.0532 (3)
O6	−0.03854 (11)	0.53320 (11)	0.26364 (6)	0.03750 (19)
N1	0.14170 (11)	0.17822 (11)	−0.15495 (7)	0.02913 (18)
C1	−0.01414 (12)	0.06686 (13)	−0.14013 (8)	0.0267 (2)
C2	−0.08456 (13)	0.11463 (13)	−0.05685 (8)	0.0274 (2)
C3	−0.24555 (14)	−0.00514 (15)	−0.04615 (9)	0.0329 (2)
H3	−0.2910	0.0290	0.0098	0.040*
C4	−0.33531 (14)	−0.17029 (15)	−0.11687 (10)	0.0375 (2)
H4	−0.4439	−0.2511	−0.1102	0.045*
C5	−0.26790 (14)	−0.22145 (14)	−0.19950 (9)	0.0352 (2)
H5	−0.3314	−0.3369	−0.2480	0.042*
C6	−0.11170 (13)	−0.10699 (13)	−0.21111 (8)	0.0300 (2)
C7	−0.04134 (15)	−0.16644 (14)	−0.29876 (9)	0.0355 (2)
C8	0.23213 (13)	0.33840 (13)	−0.08870 (8)	0.0278 (2)
H8	0.3388	0.4156	−0.0994	0.033*
C9	0.17610 (12)	0.39984 (13)	−0.00194 (7)	0.02619 (19)
C10	0.02059 (12)	0.28672 (13)	0.01161 (7)	0.02626 (19)
C11	0.12332 (13)	0.53029 (13)	0.14338 (8)	0.0285 (2)
C12	0.24320 (13)	0.55879 (13)	0.08426 (8)	0.0270 (2)
C13	0.48632 (14)	0.84001 (13)	0.18518 (8)	0.0311 (2)
H13A	0.4109	0.8901	0.2052	0.037*
H13B	0.5887	0.9326	0.1728	0.037*
C14	0.54340 (13)	0.78448 (13)	0.27476 (8)	0.0285 (2)
C15	0.67733 (15)	0.88722 (16)	0.45808 (9)	0.0390 (3)
H15A	0.7590	1.0013	0.5120	0.047*
H15B	0.7409	0.8220	0.4400	0.047*
C16	0.53376 (19)	0.7847 (2)	0.50341 (11)	0.0505 (3)
H16A	0.4600	0.6665	0.4534	0.076*
H16B	0.4650	0.8444	0.5162	0.076*
H16C	0.5826	0.7762	0.5702	0.076*
C17	0.10712 (14)	0.63031 (14)	0.24067 (9)	0.0321 (2)
C18	−0.06969 (18)	0.61382 (17)	0.35973 (10)	0.0453 (3)
H18A	−0.0846	0.7152	0.3533	0.054*
H18B	0.0287	0.6556	0.4209	0.054*
C19	−0.23018 (19)	0.47652 (19)	0.37435 (11)	0.0494 (3)
H19A	−0.3256	0.4339	0.3123	0.074*
H19B	−0.2579	0.5268	0.4376	0.074*
H19C	−0.2125	0.3787	0.3827	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0383 (4)	0.0366 (4)	0.0466 (4)	0.0170 (3)	0.0099 (3)	0.0082 (3)
F2	0.0582 (5)	0.0521 (4)	0.0312 (3)	0.0230 (4)	0.0127 (3)	0.0165 (3)
F3	0.0485 (4)	0.0340 (4)	0.0471 (4)	0.0056 (3)	0.0067 (3)	−0.0071 (3)
O1	0.0267 (3)	0.0310 (4)	0.0284 (3)	0.0128 (3)	0.0085 (3)	0.0095 (3)
O2	0.0293 (4)	0.0297 (4)	0.0281 (4)	0.0060 (3)	0.0072 (3)	0.0066 (3)
O3	0.0373 (4)	0.0289 (4)	0.0383 (4)	0.0147 (3)	0.0084 (3)	0.0102 (3)
O4	0.0367 (4)	0.0296 (4)	0.0287 (4)	0.0124 (3)	0.0053 (3)	0.0054 (3)
O5	0.0430 (5)	0.0424 (5)	0.0519 (5)	0.0087 (4)	0.0200 (4)	−0.0047 (4)
O6	0.0389 (4)	0.0354 (4)	0.0370 (4)	0.0163 (3)	0.0186 (3)	0.0079 (3)
N1	0.0281 (4)	0.0280 (4)	0.0265 (4)	0.0092 (3)	0.0070 (3)	0.0089 (3)
C1	0.0255 (4)	0.0264 (4)	0.0255 (4)	0.0095 (4)	0.0036 (4)	0.0110 (4)
C2	0.0252 (4)	0.0287 (5)	0.0271 (5)	0.0108 (4)	0.0044 (4)	0.0121 (4)
C3	0.0274 (5)	0.0362 (5)	0.0352 (5)	0.0123 (4)	0.0092 (4)	0.0168 (4)
C4	0.0270 (5)	0.0346 (5)	0.0442 (6)	0.0066 (4)	0.0076 (4)	0.0186 (5)
C5	0.0309 (5)	0.0275 (5)	0.0371 (5)	0.0071 (4)	0.0014 (4)	0.0109 (4)
C6	0.0295 (5)	0.0276 (5)	0.0278 (5)	0.0103 (4)	0.0021 (4)	0.0095 (4)
C7	0.0357 (5)	0.0278 (5)	0.0312 (5)	0.0084 (4)	0.0040 (4)	0.0050 (4)
C8	0.0253 (4)	0.0282 (5)	0.0263 (4)	0.0092 (4)	0.0072 (4)	0.0095 (4)
C9	0.0253 (4)	0.0273 (4)	0.0243 (4)	0.0112 (4)	0.0041 (3)	0.0093 (4)
C10	0.0255 (4)	0.0304 (5)	0.0242 (4)	0.0135 (4)	0.0062 (3)	0.0110 (4)
C11	0.0269 (5)	0.0289 (5)	0.0285 (5)	0.0128 (4)	0.0059 (4)	0.0088 (4)
C12	0.0261 (4)	0.0279 (5)	0.0258 (4)	0.0121 (4)	0.0049 (4)	0.0092 (4)
C13	0.0303 (5)	0.0251 (5)	0.0305 (5)	0.0086 (4)	0.0052 (4)	0.0068 (4)
C14	0.0237 (4)	0.0270 (5)	0.0302 (5)	0.0087 (4)	0.0082 (4)	0.0075 (4)
C15	0.0365 (6)	0.0431 (6)	0.0296 (5)	0.0149 (5)	0.0037 (4)	0.0088 (4)
C16	0.0531 (8)	0.0612 (8)	0.0414 (7)	0.0262 (7)	0.0187 (6)	0.0230 (6)
C17	0.0314 (5)	0.0347 (5)	0.0329 (5)	0.0178 (4)	0.0100 (4)	0.0100 (4)
C18	0.0492 (7)	0.0425 (6)	0.0410 (6)	0.0199 (6)	0.0236 (5)	0.0055 (5)
C19	0.0513 (7)	0.0509 (7)	0.0476 (7)	0.0230 (6)	0.0267 (6)	0.0139 (6)

Geometric parameters (Å, º) top

F1—C7	1.3350 (14)	C5—H5	0.9500
F2—C7	1.3412 (13)	C6—C7	1.5011 (16)
F3—C7	1.3462 (12)	C8—C9	1.4155 (14)
O1—C10	1.3444 (12)	C8—H8	0.9500
O1—C11	1.3996 (12)	C9—C10	1.3748 (13)
O2—C12	1.3463 (12)	C9—C12	1.4347 (14)
O2—C13	1.4291 (12)	C11—C12	1.3772 (14)
O3—C14	1.2019 (13)	C11—C17	1.4698 (14)
O4—C14	1.3275 (12)	C13—C14	1.5113 (15)
O4—C15	1.4591 (14)	C13—H13A	0.9900
O5—C17	1.2029 (14)	C13—H13B	0.9900
O6—C17	1.3277 (13)	C15—C16	1.5028 (18)
O6—C18	1.4511 (13)	C15—H15A	0.9900
N1—C8	1.3140 (13)	C15—H15B	0.9900
N1—C1	1.3791 (13)	C16—H16A	0.9800
C1—C2	1.4211 (14)	C16—H16B	0.9800
C1—C6	1.4215 (14)	C16—H16C	0.9800
C2—C10	1.4050 (14)	C18—C19	1.4915 (18)
C2—C3	1.4128 (14)	C18—H18A	0.9900
C3—C4	1.3655 (16)	C18—H18B	0.9900
C3—H3	0.9500	C19—H19A	0.9800
C4—C5	1.4063 (17)	C19—H19B	0.9800
C4—H4	0.9500	C19—H19C	0.9800
C5—C6	1.3722 (15)

C10—O1—C11	106.31 (8)	O1—C11—C17	113.88 (9)
C12—O2—C13	120.56 (8)	O2—C12—C11	134.90 (10)
C14—O4—C15	116.50 (9)	O2—C12—C9	118.69 (9)
C17—O6—C18	116.38 (9)	C11—C12—C9	106.39 (9)
C8—N1—C1	118.85 (9)	O2—C13—C14	111.56 (8)
N1—C1—C2	123.90 (9)	O2—C13—H13A	109.3
N1—C1—C6	119.02 (9)	C14—C13—H13A	109.3
C2—C1—C6	117.07 (9)	O2—C13—H13B	109.3
C10—C2—C3	124.76 (10)	C14—C13—H13B	109.3
C10—C2—C1	113.96 (9)	H13A—C13—H13B	108.0
C3—C2—C1	121.27 (9)	O3—C14—O4	126.09 (10)
C4—C3—C2	119.53 (10)	O3—C14—C13	124.44 (9)
C4—C3—H3	120.2	O4—C14—C13	109.47 (9)
C2—C3—H3	120.2	O4—C15—C16	111.75 (10)
C3—C4—C5	120.36 (10)	O4—C15—H15A	109.3
C3—C4—H4	119.8	C16—C15—H15A	109.3
C5—C4—H4	119.8	O4—C15—H15B	109.3
C6—C5—C4	120.94 (10)	C16—C15—H15B	109.3
C6—C5—H5	119.5	H15A—C15—H15B	107.9
C4—C5—H5	119.5	C15—C16—H16A	109.5
C5—C6—C1	120.81 (10)	C15—C16—H16B	109.5
C5—C6—C7	119.75 (10)	H16A—C16—H16B	109.5
C1—C6—C7	119.43 (9)	C15—C16—H16C	109.5
F1—C7—F2	106.89 (9)	H16A—C16—H16C	109.5
F1—C7—F3	105.90 (9)	H16B—C16—H16C	109.5
F2—C7—F3	106.11 (9)	O5—C17—O6	124.62 (10)
F1—C7—C6	112.95 (9)	O5—C17—C11	125.11 (10)
F2—C7—C6	112.93 (10)	O6—C17—C11	110.27 (9)
F3—C7—C6	111.55 (9)	O6—C18—C19	106.84 (10)
N1—C8—C9	122.26 (9)	O6—C18—H18A	110.4
N1—C8—H8	118.9	C19—C18—H18A	110.4
C9—C8—H8	118.9	O6—C18—H18B	110.4
C10—C9—C8	118.01 (9)	C19—C18—H18B	110.4
C10—C9—C12	105.74 (9)	H18A—C18—H18B	108.6
C8—C9—C12	136.23 (9)	C18—C19—H19A	109.5
O1—C10—C9	111.91 (9)	C18—C19—H19B	109.5
O1—C10—C2	125.07 (9)	H19A—C19—H19B	109.5
C9—C10—C2	123.01 (9)	C18—C19—H19C	109.5
C12—C11—O1	109.64 (9)	H19A—C19—H19C	109.5
C12—C11—C17	136.46 (10)	H19B—C19—H19C	109.5

C8—N1—C1—C2	0.10 (15)	C12—C9—C10—C2	−179.09 (9)
C8—N1—C1—C6	−179.49 (9)	C3—C2—C10—O1	1.34 (16)
N1—C1—C2—C10	−1.04 (14)	C1—C2—C10—O1	−177.96 (9)
C6—C1—C2—C10	178.55 (8)	C3—C2—C10—C9	−179.52 (9)
N1—C1—C2—C3	179.63 (9)	C1—C2—C10—C9	1.18 (14)
C6—C1—C2—C3	−0.77 (14)	C10—O1—C11—C12	0.00 (11)
C10—C2—C3—C4	−179.03 (10)	C10—O1—C11—C17	−179.01 (8)
C1—C2—C3—C4	0.21 (15)	C13—O2—C12—C11	16.43 (17)
C2—C3—C4—C5	0.33 (16)	C13—O2—C12—C9	−165.38 (9)
C3—C4—C5—C6	−0.28 (17)	O1—C11—C12—O2	178.43 (10)
C4—C5—C6—C1	−0.32 (16)	C17—C11—C12—O2	−2.9 (2)
C4—C5—C6—C7	178.76 (10)	O1—C11—C12—C9	0.08 (11)
N1—C1—C6—C5	−179.56 (9)	C17—C11—C12—C9	178.78 (12)
C2—C1—C6—C5	0.82 (15)	C10—C9—C12—O2	−178.80 (8)
N1—C1—C6—C7	1.35 (14)	C8—C9—C12—O2	2.89 (17)
C2—C1—C6—C7	−178.26 (9)	C10—C9—C12—C11	−0.14 (11)
C5—C6—C7—F1	−120.41 (11)	C8—C9—C12—C11	−178.44 (11)
C1—C6—C7—F1	58.69 (13)	C12—O2—C13—C14	64.30 (12)
C5—C6—C7—F2	118.14 (11)	C15—O4—C14—O3	0.15 (15)
C1—C6—C7—F2	−62.76 (13)	C15—O4—C14—C13	−178.99 (9)
C5—C6—C7—F3	−1.26 (15)	O2—C13—C14—O3	6.79 (14)
C1—C6—C7—F3	177.84 (9)	O2—C13—C14—O4	−174.05 (8)
C1—N1—C8—C9	0.79 (15)	C14—O4—C15—C16	−78.05 (13)
N1—C8—C9—C10	−0.65 (15)	C18—O6—C17—O5	−1.97 (18)
N1—C8—C9—C12	177.51 (10)	C18—O6—C17—C11	178.42 (10)
C11—O1—C10—C9	−0.10 (11)	C12—C11—C17—O5	2.2 (2)
C11—O1—C10—C2	179.13 (9)	O1—C11—C17—O5	−179.15 (11)
C8—C9—C10—O1	178.82 (8)	C12—C11—C17—O6	−178.20 (11)
C12—C9—C10—O1	0.15 (11)	O1—C11—C17—O6	0.45 (13)
C8—C9—C10—C2	−0.42 (14)	C17—O6—C18—C19	−174.85 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3ⁱ	0.95	2.44	3.2556 (13)	144
C13—H13B···F1ⁱⁱ	0.99	2.46	3.2829 (12)	141

Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₆F₃NO₆
M_r	411.33
Crystal system, space group	Triclinic, P1
Temperature (K)	200
a, b, c (Å)	8.9167 (3), 8.9223 (3), 13.4125 (5)
α, β, γ (°)	102.895 (1), 97.098 (2), 116.035 (1)
V (Å³)	904.22 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.56 × 0.38 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.918, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	19743, 4499, 4019
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.671

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.096, 1.04
No. of reflections	4499
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.21

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3ⁱ	0.95	2.44	3.2556 (13)	144
C13—H13B···F1ⁱⁱ	0.99	2.46	3.2829 (12)	141

Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y+1, −z.

Acknowledgements

AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India for a Young Scientist award.

References

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Volume 68| Part 12| December 2012| Pages o3389-o3390

doi:10.1107/S1600536812046843

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

Ethyl 3-(2-eth­­oxy-2-oxoeth­­oxy)-6-(tri­fluoro­meth­yl)furo[3,2-c]quinoline-2-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 3-(2-ethoxy-2-oxoethoxy)-6-(trifluoromethyl)furo[3,2-c]quinoline-2-carboxylate