Ethyl 3-(2-eth-oxy-2-oxoeth-oxy)-6-(tri-fluoro-meth-yl)furo[3,2-c]quinoline-2-carboxyl-ate.

In the title compound, C19H16F3NO6, a quinoline derivative featuring an annealated furan substituent, the mean planes of the carb-oxy 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 mol-ecules.

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 = 411.33

Triclinic,

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[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.096

S = 1.04

4499 reflections

264 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.21 e Å−3

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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046843/fj2605sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046843/fj2605Isup2.cdx

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046843/fj2605Isup4.cml

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

C19H16F3NO6	Z = 2
Mr = 411.33	F(000) = 424
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0475P)2 + 0.2384P] where P = (Fo2 + 2Fc2)/3
4499 reflections	(Δ/σ)max < 0.001
264 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .