organic compounds
Ethyl 4-oxo-8-trifluoromethyl-1,4-dihydroquinoline-3-carboxylate
aNational Institute of Technology-Karnataka, Department of Chemistry, Organic Chemistry Laboratory, Surathkal, Mangalore 575 025, India, bNational Institute of Technology-Karnataka, Department of Physics, Surathkal, Mangalore 575 025, 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
The 13H10F3NO3, contains two independent molecules with similar conformations. In the crystal, N—H⋯O hydrogen bonds link alternating independent molecules into chains in [-110]. In the chain, the quinoline planes of the independent molecules are almost perpendicular to each other, forming a dihedral angle of 89.8 (1)°. π–π interactions between the aromatic rings of quinoline bicycles related by inversion centres [for two independent centrosymmetric dimers, the shortest centroid–centroid distances are 3.495 (1) and 3.603 (1) Å] link the hydrogen-bonded chains into layers parallel to (110). Weak C—H⋯F and C—H⋯O interactions further consolidate the crystal packing.
of the title compound, CRelated literature
For background information about the pharmacological properties of quinoline derivatives, see: Holla et al. (2006); Bekhit et al. (2004); Kaur et al. (2010); Isloor et al. (2009); Vijesh et al. (2011). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995). For the synthesis of the title compound, see: Thomas et al. (2011).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2010); cell 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
10.1107/S1600536812045321/cv5354sup1.cif
contains datablocks I, global. DOI:Supporting information file. DOI: 10.1107/S1600536812045321/cv5354Isup2.cdx
Structure factors: contains datablock I. DOI: 10.1107/S1600536812045321/cv5354Isup3.hkl
Supporting information file. DOI: 10.1107/S1600536812045321/cv5354Isup4.cml
Diethyl({[3-(trifluoromethyl)phenyl]amino}methylene)malonate (10.0 g, 0.030 mol) and Dowtherm (100 ml) were heated to 250 °C for 5 h. The reaction mixture was then cooled to 25 °C and stirred in n-hexane (150 ml) for 10 min. The solid product obtained was filtered, dried and recrystallized from ethanol, yield: 8.0 g (93.0%) (Thomas et al., 2011).
C-bound H atoms were placed in calculated positions (C–H 0.95 Å for aromatic and vinylic carbon atoms and C–H 0.99 Å for methylene groups) and were included in the
in the riding model approximation, with U(H) set to 1.2Ueq(C). The H atoms of the methyl groups were allowed to rotate with a fixed angle around the C–C bond to best fit the experimental electron density (HFIX 137 in the SHELX program suite (Sheldrick, 2008)), with U(H) set to 1.5Ueq(C). Both nitrogen-bound H atoms were located on a difference Fourier map and refined freely.Data collection: APEX2 (Bruker, 2010); cell
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).Fig. 1. Two independent molecules of the title compound, with atom labels and anisotropic displacement ellipsoids drawn at the 50% probability level. | |
Fig. 2. A portion of the crystal packing viewed down the c axis. Dashed lines denote classical N–H···O hydrogen bonds. Symmetry codes: (i) -x, -y + 1, -z + 1; (ii) -x + 1, -y, -z + 1. |
C13H10F3NO3 | Z = 4 |
Mr = 285.22 | F(000) = 584 |
Triclinic, P1 | Dx = 1.577 Mg m−3 |
Hall symbol: -P 1 | Melting point = 570–568 K |
a = 9.8248 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.0222 (3) Å | Cell parameters from 9882 reflections |
c = 12.3450 (4) Å | θ = 2.5–28.3° |
α = 72.934 (1)° | µ = 0.14 mm−1 |
β = 74.167 (1)° | T = 200 K |
γ = 74.059 (1)° | Platelet, colourless |
V = 1201.67 (6) Å3 | 0.53 × 0.38 × 0.32 mm |
Bruker APEXII CCD diffractometer | 5963 independent reflections |
Radiation source: fine-focus sealed tube | 5051 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
ϕ and ω scans | θmax = 28.3°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −13→13 |
Tmin = 0.928, Tmax = 0.956 | k = −14→14 |
21419 measured reflections | l = −16→16 |
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) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0593P)2 + 0.3846P] where P = (Fo2 + 2Fc2)/3 |
5963 reflections | (Δ/σ)max < 0.001 |
371 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C13H10F3NO3 | γ = 74.059 (1)° |
Mr = 285.22 | V = 1201.67 (6) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.8248 (3) Å | Mo Kα radiation |
b = 11.0222 (3) Å | µ = 0.14 mm−1 |
c = 12.3450 (4) Å | T = 200 K |
α = 72.934 (1)° | 0.53 × 0.38 × 0.32 mm |
β = 74.167 (1)° |
Bruker APEXII CCD diffractometer | 5963 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 5051 reflections with I > 2σ(I) |
Tmin = 0.928, Tmax = 0.956 | Rint = 0.016 |
21419 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.39 e Å−3 |
5963 reflections | Δρmin = −0.23 e Å−3 |
371 parameters |
x | y | z | Uiso*/Ueq | ||
F11 | 0.33975 (9) | 0.25175 (8) | 0.03791 (8) | 0.0439 (2) | |
F12 | 0.44442 (10) | 0.35929 (10) | 0.09612 (10) | 0.0568 (3) | |
F13 | 0.47655 (10) | 0.37218 (10) | −0.08575 (9) | 0.0631 (3) | |
F21 | 0.16132 (9) | 0.25934 (8) | 0.55061 (8) | 0.0470 (2) | |
F22 | 0.05981 (10) | 0.16771 (11) | 0.71858 (8) | 0.0581 (3) | |
F23 | 0.01521 (11) | 0.13966 (11) | 0.56807 (11) | 0.0657 (3) | |
O11 | −0.20937 (11) | 0.70312 (9) | 0.17938 (8) | 0.0405 (2) | |
O12 | −0.33287 (11) | 0.58234 (11) | 0.40381 (10) | 0.0474 (3) | |
O13 | −0.19356 (10) | 0.39636 (9) | 0.48120 (8) | 0.0360 (2) | |
O21 | 0.71392 (13) | −0.18698 (10) | 0.68194 (9) | 0.0488 (3) | |
O22 | 0.83982 (11) | −0.07326 (11) | 0.79574 (11) | 0.0533 (3) | |
O23 | 0.69974 (11) | 0.11050 (11) | 0.84210 (9) | 0.0445 (2) | |
N1 | 0.12165 (11) | 0.38724 (9) | 0.19918 (9) | 0.0270 (2) | |
H1 | 0.190 (2) | 0.3151 (18) | 0.2098 (16) | 0.046 (5)* | |
N2 | 0.38130 (11) | 0.12577 (10) | 0.69417 (9) | 0.0276 (2) | |
H2 | 0.3130 (19) | 0.1915 (17) | 0.7026 (15) | 0.039 (4)* | |
C101 | 0.13071 (12) | 0.48491 (11) | 0.09948 (10) | 0.0248 (2) | |
C102 | 0.25053 (13) | 0.47904 (12) | 0.00530 (11) | 0.0291 (2) | |
C103 | 0.25240 (14) | 0.57880 (13) | −0.09286 (11) | 0.0341 (3) | |
H103 | 0.3331 | 0.5743 | −0.1560 | 0.041* | |
C104 | 0.13755 (15) | 0.68645 (13) | −0.10101 (11) | 0.0345 (3) | |
H104 | 0.1399 | 0.7543 | −0.1695 | 0.041* | |
C105 | 0.02133 (14) | 0.69401 (11) | −0.00978 (11) | 0.0307 (2) | |
H105 | −0.0566 | 0.7675 | −0.0154 | 0.037* | |
C106 | 0.01622 (12) | 0.59419 (11) | 0.09183 (10) | 0.0251 (2) | |
C107 | 0.37692 (14) | 0.36615 (14) | 0.01239 (12) | 0.0372 (3) | |
C108 | −0.11013 (12) | 0.60598 (11) | 0.18858 (10) | 0.0269 (2) | |
C109 | −0.10586 (12) | 0.49925 (11) | 0.28998 (10) | 0.0255 (2) | |
C110 | 0.00998 (12) | 0.39563 (11) | 0.28906 (10) | 0.0261 (2) | |
H110 | 0.0107 | 0.3260 | 0.3562 | 0.031* | |
C111 | −0.22344 (12) | 0.50028 (11) | 0.39440 (10) | 0.0281 (2) | |
C112 | −0.29520 (15) | 0.38902 (15) | 0.59208 (11) | 0.0383 (3) | |
H11A | −0.2959 | 0.2970 | 0.6318 | 0.046* | |
H11B | −0.3939 | 0.4329 | 0.5794 | 0.046* | |
C113 | −0.25346 (18) | 0.45247 (16) | 0.66662 (13) | 0.0459 (3) | |
H11C | −0.1546 | 0.4106 | 0.6770 | 0.069* | |
H11D | −0.3202 | 0.4435 | 0.7423 | 0.069* | |
H11E | −0.2583 | 0.5448 | 0.6292 | 0.069* | |
C201 | 0.36760 (13) | 0.02791 (11) | 0.65228 (10) | 0.0278 (2) | |
C202 | 0.24340 (14) | 0.03303 (13) | 0.61281 (11) | 0.0333 (3) | |
C203 | 0.23449 (18) | −0.07003 (15) | 0.57567 (13) | 0.0445 (3) | |
H203 | 0.1504 | −0.0669 | 0.5502 | 0.053* | |
C204 | 0.3472 (2) | −0.17898 (15) | 0.57496 (14) | 0.0498 (4) | |
H204 | 0.3396 | −0.2497 | 0.5494 | 0.060* | |
C205 | 0.46903 (18) | −0.18417 (13) | 0.61103 (12) | 0.0423 (3) | |
H205 | 0.5461 | −0.2582 | 0.6093 | 0.051* | |
C206 | 0.48144 (14) | −0.08153 (11) | 0.65054 (10) | 0.0309 (3) | |
C207 | 0.12056 (14) | 0.14904 (15) | 0.61157 (12) | 0.0390 (3) | |
C208 | 0.61343 (14) | −0.09151 (12) | 0.69029 (10) | 0.0322 (3) | |
C209 | 0.61215 (13) | 0.01330 (12) | 0.73845 (10) | 0.0295 (2) | |
C210 | 0.49545 (13) | 0.11609 (11) | 0.73754 (10) | 0.0277 (2) | |
H210 | 0.4959 | 0.1844 | 0.7697 | 0.033* | |
C211 | 0.73085 (13) | 0.00904 (13) | 0.79296 (11) | 0.0341 (3) | |
C212 | 0.79490 (17) | 0.11036 (17) | 0.91340 (13) | 0.0465 (4) | |
H21A | 0.8003 | 0.2007 | 0.9067 | 0.056* | |
H21B | 0.8936 | 0.0623 | 0.8857 | 0.056* | |
C213 | 0.74080 (19) | 0.04817 (17) | 1.03738 (13) | 0.0484 (4) | |
H21C | 0.6426 | 0.0950 | 1.0643 | 0.073* | |
H21D | 0.8048 | 0.0511 | 1.0846 | 0.073* | |
H21E | 0.7395 | −0.0424 | 1.0444 | 0.073* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F11 | 0.0417 (4) | 0.0334 (4) | 0.0518 (5) | −0.0007 (3) | −0.0053 (4) | −0.0137 (4) |
F12 | 0.0366 (4) | 0.0627 (6) | 0.0764 (7) | 0.0050 (4) | −0.0282 (5) | −0.0237 (5) |
F13 | 0.0424 (5) | 0.0589 (6) | 0.0598 (6) | 0.0010 (4) | 0.0196 (4) | −0.0110 (5) |
F21 | 0.0428 (5) | 0.0386 (4) | 0.0502 (5) | −0.0027 (3) | −0.0098 (4) | −0.0021 (4) |
F22 | 0.0385 (5) | 0.0789 (7) | 0.0411 (5) | 0.0022 (4) | 0.0011 (4) | −0.0130 (5) |
F23 | 0.0512 (6) | 0.0676 (7) | 0.0894 (8) | −0.0103 (5) | −0.0422 (6) | −0.0120 (6) |
O11 | 0.0428 (5) | 0.0338 (5) | 0.0311 (5) | 0.0145 (4) | −0.0083 (4) | −0.0078 (4) |
O12 | 0.0306 (5) | 0.0467 (6) | 0.0462 (6) | 0.0050 (4) | 0.0015 (4) | −0.0042 (5) |
O13 | 0.0353 (5) | 0.0409 (5) | 0.0252 (4) | −0.0031 (4) | −0.0036 (3) | −0.0049 (4) |
O21 | 0.0574 (6) | 0.0394 (5) | 0.0384 (5) | 0.0243 (5) | −0.0201 (5) | −0.0154 (4) |
O22 | 0.0336 (5) | 0.0522 (6) | 0.0669 (8) | 0.0066 (5) | −0.0198 (5) | −0.0091 (5) |
O23 | 0.0421 (5) | 0.0527 (6) | 0.0424 (6) | −0.0029 (4) | −0.0195 (4) | −0.0136 (5) |
N1 | 0.0258 (5) | 0.0247 (5) | 0.0271 (5) | 0.0029 (4) | −0.0081 (4) | −0.0061 (4) |
N2 | 0.0264 (5) | 0.0251 (5) | 0.0278 (5) | 0.0028 (4) | −0.0066 (4) | −0.0078 (4) |
C101 | 0.0260 (5) | 0.0251 (5) | 0.0254 (5) | −0.0036 (4) | −0.0083 (4) | −0.0082 (4) |
C102 | 0.0270 (5) | 0.0310 (6) | 0.0305 (6) | −0.0051 (4) | −0.0058 (4) | −0.0101 (5) |
C103 | 0.0346 (6) | 0.0402 (7) | 0.0286 (6) | −0.0128 (5) | −0.0019 (5) | −0.0094 (5) |
C104 | 0.0448 (7) | 0.0322 (6) | 0.0274 (6) | −0.0126 (5) | −0.0099 (5) | −0.0020 (5) |
C105 | 0.0381 (6) | 0.0250 (5) | 0.0299 (6) | −0.0034 (4) | −0.0130 (5) | −0.0055 (4) |
C106 | 0.0283 (5) | 0.0241 (5) | 0.0243 (5) | −0.0021 (4) | −0.0094 (4) | −0.0076 (4) |
C107 | 0.0269 (6) | 0.0407 (7) | 0.0392 (7) | −0.0036 (5) | −0.0005 (5) | −0.0118 (6) |
C108 | 0.0285 (5) | 0.0263 (5) | 0.0258 (5) | 0.0023 (4) | −0.0099 (4) | −0.0094 (4) |
C109 | 0.0253 (5) | 0.0264 (5) | 0.0251 (5) | −0.0016 (4) | −0.0079 (4) | −0.0079 (4) |
C110 | 0.0274 (5) | 0.0252 (5) | 0.0248 (5) | −0.0017 (4) | −0.0090 (4) | −0.0050 (4) |
C111 | 0.0260 (5) | 0.0299 (5) | 0.0291 (6) | −0.0049 (4) | −0.0063 (4) | −0.0086 (4) |
C112 | 0.0366 (7) | 0.0491 (8) | 0.0279 (6) | −0.0163 (6) | −0.0004 (5) | −0.0061 (5) |
C113 | 0.0509 (8) | 0.0551 (9) | 0.0326 (7) | −0.0138 (7) | −0.0049 (6) | −0.0128 (6) |
C201 | 0.0341 (6) | 0.0260 (5) | 0.0197 (5) | −0.0044 (4) | −0.0050 (4) | −0.0026 (4) |
C202 | 0.0383 (6) | 0.0350 (6) | 0.0250 (6) | −0.0102 (5) | −0.0082 (5) | −0.0010 (5) |
C203 | 0.0595 (9) | 0.0459 (8) | 0.0352 (7) | −0.0221 (7) | −0.0159 (6) | −0.0045 (6) |
C204 | 0.0807 (12) | 0.0363 (7) | 0.0400 (8) | −0.0201 (7) | −0.0168 (8) | −0.0093 (6) |
C205 | 0.0650 (9) | 0.0265 (6) | 0.0319 (6) | −0.0031 (6) | −0.0107 (6) | −0.0074 (5) |
C206 | 0.0424 (7) | 0.0249 (5) | 0.0202 (5) | −0.0009 (5) | −0.0062 (5) | −0.0038 (4) |
C207 | 0.0313 (6) | 0.0496 (8) | 0.0348 (7) | −0.0095 (6) | −0.0103 (5) | −0.0042 (6) |
C208 | 0.0381 (6) | 0.0282 (6) | 0.0200 (5) | 0.0072 (5) | −0.0064 (4) | −0.0032 (4) |
C209 | 0.0283 (5) | 0.0296 (6) | 0.0233 (5) | 0.0018 (4) | −0.0053 (4) | −0.0029 (4) |
C210 | 0.0279 (5) | 0.0269 (5) | 0.0247 (5) | −0.0012 (4) | −0.0046 (4) | −0.0057 (4) |
C211 | 0.0295 (6) | 0.0372 (6) | 0.0282 (6) | −0.0037 (5) | −0.0066 (5) | 0.0010 (5) |
C212 | 0.0445 (8) | 0.0630 (9) | 0.0355 (7) | −0.0223 (7) | −0.0154 (6) | −0.0003 (6) |
C213 | 0.0564 (9) | 0.0523 (9) | 0.0335 (7) | −0.0136 (7) | −0.0072 (6) | −0.0055 (6) |
F11—C107 | 1.3341 (16) | C108—C109 | 1.4457 (16) |
F12—C107 | 1.3470 (17) | C109—C110 | 1.3735 (15) |
F13—C107 | 1.3310 (16) | C109—C111 | 1.4782 (16) |
F21—C207 | 1.3307 (17) | C110—H110 | 0.9500 |
F22—C207 | 1.3437 (17) | C112—C113 | 1.498 (2) |
F23—C207 | 1.3285 (16) | C112—H11A | 0.9900 |
O11—C108 | 1.2351 (14) | C112—H11B | 0.9900 |
O12—C111 | 1.2029 (15) | C113—H11C | 0.9800 |
O13—C111 | 1.3464 (15) | C113—H11D | 0.9800 |
O13—C112 | 1.4529 (15) | C113—H11E | 0.9800 |
O21—C208 | 1.2370 (15) | C201—C206 | 1.4027 (16) |
O22—C211 | 1.1994 (16) | C201—C202 | 1.4141 (17) |
O23—C211 | 1.3495 (18) | C202—C203 | 1.375 (2) |
O23—C212 | 1.4479 (17) | C202—C207 | 1.4976 (19) |
N1—C110 | 1.3355 (15) | C203—C204 | 1.393 (2) |
N1—C101 | 1.3773 (15) | C203—H203 | 0.9500 |
N1—H1 | 0.892 (19) | C204—C205 | 1.368 (2) |
N2—C210 | 1.3358 (15) | C204—H204 | 0.9500 |
N2—C201 | 1.3763 (15) | C205—C206 | 1.4017 (18) |
N2—H2 | 0.851 (18) | C205—H205 | 0.9500 |
C101—C106 | 1.4043 (15) | C206—C208 | 1.4737 (18) |
C101—C102 | 1.4132 (16) | C208—C209 | 1.4420 (18) |
C102—C103 | 1.3765 (18) | C209—C210 | 1.3727 (15) |
C102—C107 | 1.4981 (17) | C209—C211 | 1.4815 (17) |
C103—C104 | 1.3956 (19) | C210—H210 | 0.9500 |
C103—H103 | 0.9500 | C212—C213 | 1.495 (2) |
C104—C105 | 1.3712 (18) | C212—H21A | 0.9900 |
C104—H104 | 0.9500 | C212—H21B | 0.9900 |
C105—C106 | 1.4044 (16) | C213—H21C | 0.9800 |
C105—H105 | 0.9500 | C213—H21D | 0.9800 |
C106—C108 | 1.4757 (16) | C213—H21E | 0.9800 |
C111—O13—C112 | 117.59 (10) | H11C—C113—H11D | 109.5 |
C211—O23—C212 | 117.55 (12) | C112—C113—H11E | 109.5 |
C110—N1—C101 | 121.95 (10) | H11C—C113—H11E | 109.5 |
C110—N1—H1 | 114.9 (12) | H11D—C113—H11E | 109.5 |
C101—N1—H1 | 123.2 (12) | N2—C201—C206 | 118.05 (11) |
C210—N2—C201 | 121.93 (10) | N2—C201—C202 | 122.66 (11) |
C210—N2—H2 | 115.4 (11) | C206—C201—C202 | 119.28 (11) |
C201—N2—H2 | 122.2 (11) | C203—C202—C201 | 119.74 (13) |
N1—C101—C106 | 118.41 (10) | C203—C202—C207 | 119.36 (13) |
N1—C101—C102 | 122.48 (10) | C201—C202—C207 | 120.90 (11) |
C106—C101—C102 | 119.12 (10) | C202—C203—C204 | 120.80 (14) |
C103—C102—C101 | 119.82 (11) | C202—C203—H203 | 119.6 |
C103—C102—C107 | 119.71 (11) | C204—C203—H203 | 119.6 |
C101—C102—C107 | 120.46 (11) | C205—C204—C203 | 120.02 (13) |
C102—C103—C104 | 121.00 (12) | C205—C204—H204 | 120.0 |
C102—C103—H103 | 119.5 | C203—C204—H204 | 120.0 |
C104—C103—H103 | 119.5 | C204—C205—C206 | 120.81 (13) |
C105—C104—C103 | 119.78 (11) | C204—C205—H205 | 119.6 |
C105—C104—H104 | 120.1 | C206—C205—H205 | 119.6 |
C103—C104—H104 | 120.1 | C205—C206—C201 | 119.33 (13) |
C104—C105—C106 | 120.70 (11) | C205—C206—C208 | 119.22 (12) |
C104—C105—H105 | 119.7 | C201—C206—C208 | 121.44 (11) |
C106—C105—H105 | 119.7 | F23—C207—F21 | 106.70 (11) |
C101—C106—C105 | 119.58 (11) | F23—C207—F22 | 106.69 (12) |
C101—C106—C108 | 121.19 (10) | F21—C207—F22 | 105.13 (12) |
C105—C106—C108 | 119.22 (10) | F23—C207—C202 | 112.96 (13) |
F13—C107—F11 | 106.66 (11) | F21—C207—C202 | 113.00 (11) |
F13—C107—F12 | 106.61 (11) | F22—C207—C202 | 111.81 (11) |
F11—C107—F12 | 105.45 (12) | O21—C208—C209 | 125.29 (13) |
F13—C107—C102 | 112.78 (12) | O21—C208—C206 | 119.16 (12) |
F11—C107—C102 | 113.23 (10) | C209—C208—C206 | 115.54 (10) |
F12—C107—C102 | 111.58 (11) | C210—C209—C208 | 118.91 (11) |
O11—C108—C109 | 124.72 (11) | C210—C209—C211 | 119.79 (11) |
O11—C108—C106 | 119.80 (11) | C208—C209—C211 | 121.25 (11) |
C109—C108—C106 | 115.48 (10) | N2—C210—C209 | 123.90 (11) |
C110—C109—C108 | 119.21 (10) | N2—C210—H210 | 118.0 |
C110—C109—C111 | 119.66 (10) | C209—C210—H210 | 118.0 |
C108—C109—C111 | 121.13 (10) | O22—C211—O23 | 123.44 (13) |
N1—C110—C109 | 123.71 (10) | O22—C211—C209 | 125.73 (13) |
N1—C110—H110 | 118.1 | O23—C211—C209 | 110.82 (10) |
C109—C110—H110 | 118.1 | O23—C212—C213 | 110.57 (12) |
O12—C111—O13 | 122.73 (11) | O23—C212—H21A | 109.5 |
O12—C111—C109 | 125.78 (11) | C213—C212—H21A | 109.5 |
O13—C111—C109 | 111.49 (10) | O23—C212—H21B | 109.5 |
O13—C112—C113 | 110.26 (11) | C213—C212—H21B | 109.5 |
O13—C112—H11A | 109.6 | H21A—C212—H21B | 108.1 |
C113—C112—H11A | 109.6 | C212—C213—H21C | 109.5 |
O13—C112—H11B | 109.6 | C212—C213—H21D | 109.5 |
C113—C112—H11B | 109.6 | H21C—C213—H21D | 109.5 |
H11A—C112—H11B | 108.1 | C212—C213—H21E | 109.5 |
C112—C113—H11C | 109.5 | H21C—C213—H21E | 109.5 |
C112—C113—H11D | 109.5 | H21D—C213—H21E | 109.5 |
C110—N1—C101—C106 | −2.05 (16) | C210—N2—C201—C206 | −3.23 (17) |
C110—N1—C101—C102 | 177.88 (10) | C210—N2—C201—C202 | 175.92 (11) |
N1—C101—C102—C103 | 178.98 (11) | N2—C201—C202—C203 | −177.79 (12) |
C106—C101—C102—C103 | −1.09 (17) | C206—C201—C202—C203 | 1.35 (18) |
N1—C101—C102—C107 | −2.20 (17) | N2—C201—C202—C207 | 1.81 (18) |
C106—C101—C102—C107 | 177.73 (11) | C206—C201—C202—C207 | −179.05 (11) |
C101—C102—C103—C104 | 0.15 (18) | C201—C202—C203—C204 | −0.8 (2) |
C107—C102—C103—C104 | −178.67 (12) | C207—C202—C203—C204 | 179.55 (13) |
C102—C103—C104—C105 | 0.53 (19) | C202—C203—C204—C205 | −0.3 (2) |
C103—C104—C105—C106 | −0.26 (19) | C203—C204—C205—C206 | 0.9 (2) |
N1—C101—C106—C105 | −178.71 (10) | C204—C205—C206—C201 | −0.4 (2) |
C102—C101—C106—C105 | 1.35 (16) | C204—C205—C206—C208 | 179.11 (13) |
N1—C101—C106—C108 | 0.99 (16) | N2—C201—C206—C205 | 178.44 (11) |
C102—C101—C106—C108 | −178.94 (10) | C202—C201—C206—C205 | −0.74 (18) |
C104—C105—C106—C101 | −0.69 (17) | N2—C201—C206—C208 | −1.05 (17) |
C104—C105—C106—C108 | 179.60 (11) | C202—C201—C206—C208 | 179.77 (11) |
C103—C102—C107—F13 | −4.70 (18) | C203—C202—C207—F23 | −2.68 (18) |
C101—C102—C107—F13 | 176.48 (11) | C201—C202—C207—F23 | 177.71 (12) |
C103—C102—C107—F11 | −125.94 (13) | C203—C202—C207—F21 | −123.94 (14) |
C101—C102—C107—F11 | 55.24 (16) | C201—C202—C207—F21 | 56.46 (16) |
C103—C102—C107—F12 | 115.27 (14) | C203—C202—C207—F22 | 117.68 (14) |
C101—C102—C107—F12 | −63.55 (15) | C201—C202—C207—F22 | −61.92 (16) |
C101—C106—C108—O11 | −179.90 (11) | C205—C206—C208—O21 | 3.99 (18) |
C105—C106—C108—O11 | −0.19 (17) | C201—C206—C208—O21 | −176.53 (12) |
C101—C106—C108—C109 | 0.70 (16) | C205—C206—C208—C209 | −175.03 (11) |
C105—C106—C108—C109 | −179.60 (10) | C201—C206—C208—C209 | 4.46 (17) |
O11—C108—C109—C110 | 179.19 (12) | O21—C208—C209—C210 | 177.19 (12) |
C106—C108—C109—C110 | −1.43 (15) | C206—C208—C209—C210 | −3.86 (16) |
O11—C108—C109—C111 | −1.12 (18) | O21—C208—C209—C211 | −5.5 (2) |
C106—C108—C109—C111 | 178.25 (10) | C206—C208—C209—C211 | 173.49 (11) |
C101—N1—C110—C109 | 1.34 (17) | C201—N2—C210—C209 | 3.95 (18) |
C108—C109—C110—N1 | 0.50 (17) | C208—C209—C210—N2 | −0.11 (18) |
C111—C109—C110—N1 | −179.19 (10) | C211—C209—C210—N2 | −177.50 (11) |
C112—O13—C111—O12 | −3.68 (18) | C212—O23—C211—O22 | −7.8 (2) |
C112—O13—C111—C109 | 175.91 (10) | C212—O23—C211—C209 | 171.24 (11) |
C110—C109—C111—O12 | −176.54 (12) | C210—C209—C211—O22 | −177.47 (13) |
C108—C109—C111—O12 | 3.78 (19) | C208—C209—C211—O22 | 5.2 (2) |
C110—C109—C111—O13 | 3.89 (15) | C210—C209—C211—O23 | 3.55 (16) |
C108—C109—C111—O13 | −175.80 (10) | C208—C209—C211—O23 | −173.77 (11) |
C111—O13—C112—C113 | −90.46 (14) | C211—O23—C212—C213 | −91.90 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O21i | 0.892 (19) | 1.875 (19) | 2.6588 (13) | 145.5 (16) |
N2—H2···O11ii | 0.851 (18) | 2.011 (17) | 2.7178 (13) | 139.9 (16) |
N2—H2···O12ii | 0.851 (18) | 2.487 (17) | 3.0380 (15) | 123.2 (14) |
C212—H21B···F22iii | 0.99 | 2.46 | 3.0909 (18) | 121 |
C204—H204···O13iv | 0.95 | 2.60 | 3.4691 (18) | 153 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+1, −z+1; (iii) x+1, y, z; (iv) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C13H10F3NO3 |
Mr | 285.22 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 200 |
a, b, c (Å) | 9.8248 (3), 11.0222 (3), 12.3450 (4) |
α, β, γ (°) | 72.934 (1), 74.167 (1), 74.059 (1) |
V (Å3) | 1201.67 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.14 |
Crystal size (mm) | 0.53 × 0.38 × 0.32 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.928, 0.956 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21419, 5963, 5051 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.116, 1.04 |
No. of reflections | 5963 |
No. of parameters | 371 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.39, −0.23 |
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).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O21i | 0.892 (19) | 1.875 (19) | 2.6588 (13) | 145.5 (16) |
N2—H2···O11ii | 0.851 (18) | 2.011 (17) | 2.7178 (13) | 139.9 (16) |
N2—H2···O12ii | 0.851 (18) | 2.487 (17) | 3.0380 (15) | 123.2 (14) |
C212—H21B···F22iii | 0.99 | 2.46 | 3.0909 (18) | 120.8 |
C204—H204···O13iv | 0.95 | 2.60 | 3.4691 (18) | 152.9 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+1, −z+1; (iii) x+1, y, z; (iv) −x, −y, −z+1. |
Acknowledgements
AMI thanks the Board for Research in Nuclear Sciences, Department of Atomic Energy, Government of India, for the Young Scientist award.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Quinoline derivatives constitute an important class of compounds that are widely found in plants. A number of synthetic analogues have been developed over the years. Some of them exhibit remarkable effects such as antimicrobial, anti-inflammatory and antimalarial (Holla et al., 2006; Bekhit et al., 2004; Kaur et al., 2010). This follows a broader trend that shows nitrogen-containing heterocycles to be among pharmaceutically active and interesting compounds (Isloor et al., 2009; Vijesh et al., 2011) which justifies our continuing efforts in designing novel heterocyclic molecules of biological importance and study their respective molecular and crystal structure.
The title compound is a derivative of 1,4-dihydroquinoline and does not adopt its aromatic tautomeric form as a quinoline derivative. There are two independent molecules in the asymmetric unit (Fig. 1).
In the crystal, classical N—H···O hydrogen bonds (Table 1) link the alternating independent molecules into chains in [-110] (Fig. 2). In the chain, the quinoline planes of independent molecules are almost perpendicular to each other forming a dihedral angle of 89.8 (1)°. The π–π interactions between the aromatic rings of the quinoline bicycles related by inversion centres [for two independent centrosymmetric dimers the shortest intercentroid distances are 3.495 (1) and 3.603 (1) Å, respectively] link hydrogen-bonded chains into layers parallel to the (110) plane. Weak intermolecular C–H···F contacts are observed next to intermolecular C–H···O contacts (Table 1). In every case, the range of these contacts falls by more than 0.1 Å below the sum of van-der-Waals radii of the atoms participating in them. While the C–H···O contacts stem from one of the hydrogen atoms on the phenyl moiety bearing the trifluoromethyl substituent and apply the ethereal oxygen atom as acceptor, the classical hydrogen bonds invariably have double bonded oxygen atoms as acceptors. These hydrogen bonds intermittently connect the two different molecules present in the asymmetric unit into chains along [-110] and show bifurcation between the two double bonded oxygen atoms in one case. In total, these contacts connect the molecules to planes parallel to ab. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for the classical hydrogen bonds is DDD on the unary level (taking into account the bifurcation). The descriptor for the C–H···O contacts is D while a C11(11) descriptor is found for the C–H···F contacts on the same level.