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In the title mol­ecule, C18H13F3N2O, the mean planes of the quinolin-4-yl and phenylethanone groups are twisted, with a dihedral angle of 57.4 (1)°. In the crystal structure, inter­molecular N—H...O hydrogen bonds link the mol­ecules into zigzag chains running in the direction [011].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035544/cv2279sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035544/cv2279Isup2.hkl
Contains datablock I

CCDC reference: 657842

Key indicators

  • Single-crystal X-ray study
  • T = 203 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.029
  • wR factor = 0.076
  • Data-to-parameter ratio = 8.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.78 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C18 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C18 H13 F3 N2 O
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.778 Tmax scaled 0.778 Tmin scaled 0.707 REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 87.78 From the CIF: _reflns_number_total 1777 Count of symmetry unique reflns 1785 Completeness (_total/calc) 99.55% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

In recent years fluorinated compounds find much importance in the pharmaceutical field. Fluorinated compounds in general, fluorinated heterocycles in particular, are those focused on much in modern-day medicinal chemistry. Incorporation of a fluorine atom instead of hydrogen one can alter the course of the reaction as well as its biological activities. Further introduction of a fluorine atom as the CF3 group provides a more lipophilically and pharmacologically interesting compound compared to their non fluorinated analogues. The trifluoromethyl substituted compounds have been reported to possess biological activities as herbicides, fungicides and inhibitors for platelet aggregation. Quinolines are known to researchers for many years because a large number of natural products contain these heterocycles. They are found in numerous commericial products, including pharmaceuticals, fragrances and dyes. Quinoline alkaloids such as quinine, chloroquin, mefloquine and amodiaquine are used as efficient drugs for the treatment of malaria. Several quinoline derivatives have been evaluated in vitro against several parasites and HTLV-1 transformed cells. Prompted by the varied biological activities, the crystal structure of the title compound, C18H13F3N2O, (I), is here reported.

In (I) (Fig. 1), the mean planes of the quinolin-4-yl and phenyl-ethanone groups are twisted with a dihedral angle of 57.4 (1)°. In the crystal, intermolecular hydrogen bond interactions occur between N2–H2B and C5–H5A both to the same O1 (Table 1), which link the molecules into zigzag chains running in direction [011] (Fig. 2).

Related literature top

For related structures, see: Lynch & McClenaghan (2001); Yathirajan et al. (2007). For related literature, see: Kucukguzel et al. (2000); Jung et al. (2002); Franck et al. (2004).

Experimental top

A mixture of 4-chloro-8-(trifluoromethyl)quinoline (2.31 g, 0.01 mol), 1-(4-aminophenyl)ethanone, (1.35 g, 0.01 mol) and anhydrous potassium carbonate (2.76 g 0.02 mol) in 30 ml of dimethyl formamide (DMF) was heated over water bath for 6 h. The resulting mixture was filtered and the solution was concentrated on water bath to get the title compound. The crystals were obtained from acetone by slow evapoaration (M.p. 509 K). Elemental analysis found: C: 65.36; H: 3.94; N: 8.41%. C18H13F3N2O requires C, 65.45, H, 3.97, N, 8.48%

Refinement top

Atom H2B was located on a difference map, but placed in idealized position, N—H = 0.87 Å. C-bound H atoms were geometrically positioned, C—H = 0.94–0.97 Å. All H-atoms were refined as riding, with Uiso(H) = 1.2–1.5 Ueq of the parent atom. In the absence of any significant anomalous scatters in the molecule, 1777 Friedel pairs were merged before the final refinement.

Structure description top

In recent years fluorinated compounds find much importance in the pharmaceutical field. Fluorinated compounds in general, fluorinated heterocycles in particular, are those focused on much in modern-day medicinal chemistry. Incorporation of a fluorine atom instead of hydrogen one can alter the course of the reaction as well as its biological activities. Further introduction of a fluorine atom as the CF3 group provides a more lipophilically and pharmacologically interesting compound compared to their non fluorinated analogues. The trifluoromethyl substituted compounds have been reported to possess biological activities as herbicides, fungicides and inhibitors for platelet aggregation. Quinolines are known to researchers for many years because a large number of natural products contain these heterocycles. They are found in numerous commericial products, including pharmaceuticals, fragrances and dyes. Quinoline alkaloids such as quinine, chloroquin, mefloquine and amodiaquine are used as efficient drugs for the treatment of malaria. Several quinoline derivatives have been evaluated in vitro against several parasites and HTLV-1 transformed cells. Prompted by the varied biological activities, the crystal structure of the title compound, C18H13F3N2O, (I), is here reported.

In (I) (Fig. 1), the mean planes of the quinolin-4-yl and phenyl-ethanone groups are twisted with a dihedral angle of 57.4 (1)°. In the crystal, intermolecular hydrogen bond interactions occur between N2–H2B and C5–H5A both to the same O1 (Table 1), which link the molecules into zigzag chains running in direction [011] (Fig. 2).

For related structures, see: Lynch & McClenaghan (2001); Yathirajan et al. (2007). For related literature, see: Kucukguzel et al. (2000); Jung et al. (2002); Franck et al. (2004).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Molecular structure of C18H13F3N2O, (I), showing atom labeling and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of C18H13F3N2O viewed down the b axis. Dashed lines indicate N–H···O and C–H···O hydrogen bonds.
1-(4-{[8-(Trifluoromethyl)quinolin-4-yl]amino}phenyl)ethanone top
Crystal data top
C18H13F3N2ODx = 1.460 Mg m3
Mr = 330.30Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pna21Cell parameters from 5931 reflections
a = 24.4690 (6) Åθ = 4.7–32.5°
b = 4.5342 (2) ŵ = 1.00 mm1
c = 13.5408 (3) ÅT = 203 K
V = 1502.32 (8) Å3Chunk, pale yellow
Z = 40.46 × 0.37 × 0.25 mm
F(000) = 680
Data collection top
Oxford Diffraction Gemini R
diffractometer
1777 independent reflections
Radiation source: fine-focus sealed tube1657 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
Detector resolution: 10.5081 pixels mm-1θmax = 87.8°, θmin = 10.3°
φ and ω scansh = 3123
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
k = 55
Tmin = 0.909, Tmax = 1.000l = 1717
8038 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H-atom parameters constrained
S = 1.18 w = 1/[σ2(Fo2) + (0.0428P)2 + 0.1154P]
where P = (Fo2 + 2Fc2)/3
1777 reflections(Δ/σ)max = 0.010
218 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.14 e Å3
Crystal data top
C18H13F3N2OV = 1502.32 (8) Å3
Mr = 330.30Z = 4
Orthorhombic, Pna21Cu Kα radiation
a = 24.4690 (6) ŵ = 1.00 mm1
b = 4.5342 (2) ÅT = 203 K
c = 13.5408 (3) Å0.46 × 0.37 × 0.25 mm
Data collection top
Oxford Diffraction Gemini R
diffractometer
1777 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
1657 reflections with I > 2σ(I)
Tmin = 0.909, Tmax = 1.000Rint = 0.017
8038 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.076H-atom parameters constrained
S = 1.18Δρmax = 0.16 e Å3
1777 reflectionsΔρmin = 0.14 e Å3
218 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
xyzUiso*/Ueq
F10.12637 (5)0.0249 (3)0.31930 (11)0.0505 (3)
F20.13325 (5)0.3655 (3)0.23050 (13)0.0542 (4)
F30.14003 (5)0.0597 (3)0.16310 (11)0.0522 (4)
O10.30621 (6)0.7599 (4)0.62756 (11)0.0519 (4)
N10.03926 (6)0.4026 (4)0.35402 (12)0.0316 (3)
N20.13031 (6)0.4360 (4)0.29863 (11)0.0368 (4)
H2B0.14080.36920.24140.044*
C10.00518 (8)0.5549 (5)0.40932 (15)0.0331 (4)
H1A0.02030.66160.46220.040*
C20.05134 (8)0.5721 (4)0.39652 (14)0.0321 (4)
H2A0.07270.68600.43980.038*
C30.07551 (7)0.4197 (4)0.31947 (13)0.0284 (4)
C40.04056 (7)0.2480 (4)0.25738 (12)0.0259 (3)
C50.06027 (8)0.0777 (4)0.17722 (14)0.0323 (4)
H5A0.09800.07190.16430.039*
C60.02561 (9)0.0770 (5)0.11878 (15)0.0375 (5)
H6A0.03950.18820.06580.045*
C70.03120 (8)0.0723 (5)0.13691 (15)0.0356 (4)
H7A0.05490.17960.09580.043*
C80.05185 (8)0.0878 (4)0.21401 (14)0.0306 (4)
C90.01659 (7)0.2505 (4)0.27749 (13)0.0266 (3)
C100.11244 (8)0.0927 (4)0.23199 (18)0.0373 (4)
C110.17126 (7)0.5504 (5)0.36096 (13)0.0316 (4)
C120.21175 (7)0.7282 (5)0.32065 (14)0.0357 (4)
H12A0.21030.77960.25350.043*
C130.25430 (8)0.8302 (5)0.37915 (14)0.0348 (4)
H13A0.28150.95050.35140.042*
C140.25686 (7)0.7552 (5)0.47883 (15)0.0314 (4)
C150.21584 (7)0.5776 (5)0.51915 (13)0.0363 (4)
H15A0.21710.52750.58650.044*
C160.17363 (8)0.4753 (5)0.46115 (14)0.0371 (5)
H16A0.14640.35490.48890.045*
C170.30242 (7)0.8529 (5)0.54293 (15)0.0367 (4)
C180.34396 (9)1.0632 (6)0.50333 (19)0.0498 (6)
H18A0.37091.10500.55400.075*
H18B0.32611.24500.48380.075*
H18C0.36190.97620.44650.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0364 (6)0.0521 (8)0.0630 (8)0.0090 (6)0.0096 (6)0.0003 (7)
F20.0363 (6)0.0363 (6)0.0902 (10)0.0073 (5)0.0131 (7)0.0046 (8)
F30.0365 (6)0.0493 (7)0.0707 (9)0.0057 (6)0.0151 (6)0.0126 (7)
O10.0369 (7)0.0842 (13)0.0346 (7)0.0088 (8)0.0094 (6)0.0041 (8)
N10.0266 (7)0.0337 (8)0.0346 (8)0.0006 (7)0.0037 (6)0.0004 (7)
N20.0250 (7)0.0607 (12)0.0246 (8)0.0036 (7)0.0007 (6)0.0070 (8)
C10.0324 (8)0.0370 (11)0.0301 (8)0.0016 (8)0.0053 (8)0.0037 (8)
C20.0318 (8)0.0368 (10)0.0276 (8)0.0053 (8)0.0001 (7)0.0035 (8)
C30.0258 (8)0.0363 (10)0.0232 (7)0.0007 (7)0.0005 (7)0.0040 (8)
C40.0274 (7)0.0279 (8)0.0223 (7)0.0012 (7)0.0000 (6)0.0042 (7)
C50.0296 (8)0.0367 (10)0.0305 (9)0.0037 (8)0.0017 (7)0.0007 (8)
C60.0414 (10)0.0376 (11)0.0334 (9)0.0051 (9)0.0007 (8)0.0077 (9)
C70.0377 (9)0.0329 (10)0.0363 (10)0.0010 (8)0.0079 (8)0.0048 (8)
C80.0302 (8)0.0265 (9)0.0353 (9)0.0006 (7)0.0043 (7)0.0042 (8)
C90.0280 (7)0.0249 (8)0.0269 (8)0.0007 (7)0.0014 (7)0.0044 (7)
C100.0299 (9)0.0296 (9)0.0524 (12)0.0012 (8)0.0052 (9)0.0014 (10)
C110.0226 (8)0.0461 (11)0.0259 (8)0.0003 (8)0.0007 (7)0.0017 (8)
C120.0301 (8)0.0528 (12)0.0243 (8)0.0030 (9)0.0002 (7)0.0027 (8)
C130.0286 (8)0.0432 (11)0.0326 (9)0.0044 (8)0.0027 (7)0.0018 (8)
C140.0235 (7)0.0407 (10)0.0299 (8)0.0020 (8)0.0010 (7)0.0044 (8)
C150.0292 (9)0.0555 (13)0.0241 (8)0.0024 (9)0.0008 (7)0.0027 (8)
C160.0284 (9)0.0527 (13)0.0303 (10)0.0077 (9)0.0006 (7)0.0050 (9)
C170.0272 (8)0.0476 (11)0.0352 (10)0.0037 (8)0.0010 (8)0.0107 (9)
C180.0384 (10)0.0592 (15)0.0518 (13)0.0143 (11)0.0038 (10)0.0103 (11)
Geometric parameters (Å, º) top
F1—C101.341 (3)C7—C81.368 (3)
F2—C101.338 (2)C7—H7A0.9400
F3—C101.343 (2)C8—C91.424 (3)
O1—C171.225 (3)C8—C101.502 (3)
N1—C11.316 (3)C11—C121.389 (3)
N1—C91.363 (2)C11—C161.400 (3)
N2—C31.372 (2)C12—C131.388 (3)
N2—C111.409 (2)C12—H12A0.9400
N2—H2B0.8700C13—C141.393 (3)
C1—C21.396 (3)C13—H13A0.9400
C1—H1A0.9400C14—C151.398 (3)
C2—C31.384 (3)C14—C171.480 (3)
C2—H2A0.9400C15—C161.378 (3)
C3—C41.430 (2)C15—H15A0.9400
C4—C51.417 (3)C16—H16A0.9400
C4—C91.425 (2)C17—C181.493 (3)
C5—C61.356 (3)C18—H18A0.9700
C5—H5A0.9400C18—H18B0.9700
C6—C71.412 (3)C18—H18C0.9700
C6—H6A0.9400
C1—N1—C9116.11 (15)F2—C10—F3105.89 (16)
C3—N2—C11126.27 (15)F1—C10—F3106.28 (15)
C3—N2—H2B116.9F2—C10—C8112.74 (16)
C11—N2—H2B116.9F1—C10—C8112.83 (17)
N1—C1—C2125.90 (18)F3—C10—C8112.08 (18)
N1—C1—H1A117.0C12—C11—C16119.50 (18)
C2—C1—H1A117.0C12—C11—N2119.05 (16)
C3—C2—C1119.27 (17)C16—C11—N2121.36 (18)
C3—C2—H2A120.4C13—C12—C11120.28 (17)
C1—C2—H2A120.4C13—C12—H12A119.9
N2—C3—C2123.06 (17)C11—C12—H12A119.9
N2—C3—C4119.53 (16)C12—C13—C14120.37 (19)
C2—C3—C4117.36 (16)C12—C13—H13A119.8
C5—C4—C9119.01 (15)C14—C13—H13A119.8
C5—C4—C3122.93 (15)C13—C14—C15119.11 (18)
C9—C4—C3118.06 (15)C13—C14—C17121.93 (18)
C6—C5—C4121.08 (17)C15—C14—C17118.95 (18)
C6—C5—H5A119.5C16—C15—C14120.64 (17)
C4—C5—H5A119.5C16—C15—H15A119.7
C5—C6—C7120.45 (19)C14—C15—H15A119.7
C5—C6—H6A119.8C15—C16—C11120.10 (18)
C7—C6—H6A119.8C15—C16—H16A120.0
C8—C7—C6120.29 (18)C11—C16—H16A120.0
C8—C7—H7A119.9O1—C17—C14120.18 (19)
C6—C7—H7A119.9O1—C17—C18120.28 (19)
C7—C8—C9120.77 (17)C14—C17—C18119.54 (19)
C7—C8—C10119.72 (17)C17—C18—H18A109.5
C9—C8—C10119.51 (18)C17—C18—H18B109.5
N1—C9—C4123.29 (16)H18A—C18—H18B109.5
N1—C9—C8118.32 (16)C17—C18—H18C109.5
C4—C9—C8118.38 (16)H18A—C18—H18C109.5
F2—C10—F1106.50 (18)H18B—C18—H18C109.5
C9—N1—C1—C20.3 (3)C7—C8—C9—C41.5 (3)
N1—C1—C2—C30.2 (3)C10—C8—C9—C4178.49 (16)
C11—N2—C3—C214.5 (3)C7—C8—C10—F2122.3 (2)
C11—N2—C3—C4168.10 (19)C9—C8—C10—F257.6 (3)
C1—C2—C3—N2176.70 (19)C7—C8—C10—F1117.0 (2)
C1—C2—C3—C40.8 (3)C9—C8—C10—F163.1 (2)
N2—C3—C4—C53.6 (3)C7—C8—C10—F32.9 (3)
C2—C3—C4—C5178.81 (18)C9—C8—C10—F3177.01 (16)
N2—C3—C4—C9176.21 (17)C3—N2—C11—C12137.8 (2)
C2—C3—C4—C91.4 (2)C3—N2—C11—C1645.8 (3)
C9—C4—C5—C61.3 (3)C16—C11—C12—C130.1 (3)
C3—C4—C5—C6178.56 (19)N2—C11—C12—C13176.3 (2)
C4—C5—C6—C70.2 (3)C11—C12—C13—C140.0 (3)
C5—C6—C7—C80.3 (3)C12—C13—C14—C150.4 (3)
C6—C7—C8—C90.4 (3)C12—C13—C14—C17178.27 (19)
C6—C7—C8—C10179.56 (19)C13—C14—C15—C160.6 (3)
C1—N1—C9—C40.9 (3)C17—C14—C15—C16178.1 (2)
C1—N1—C9—C8178.53 (18)C14—C15—C16—C110.4 (3)
C5—C4—C9—N1178.66 (18)C12—C11—C16—C150.1 (3)
C3—C4—C9—N11.5 (2)N2—C11—C16—C15176.5 (2)
C5—C4—C9—C81.9 (2)C13—C14—C17—O1172.9 (2)
C3—C4—C9—C8177.96 (17)C15—C14—C17—O15.8 (3)
C7—C8—C9—N1179.05 (18)C13—C14—C17—C186.5 (3)
C10—C8—C9—N11.0 (3)C15—C14—C17—C18174.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O1i0.872.082.901 (2)158
C5—H5A···O1i0.942.543.436 (2)159
Symmetry code: (i) x1/2, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC18H13F3N2O
Mr330.30
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)203
a, b, c (Å)24.4690 (6), 4.5342 (2), 13.5408 (3)
V3)1502.32 (8)
Z4
Radiation typeCu Kα
µ (mm1)1.00
Crystal size (mm)0.46 × 0.37 × 0.25
Data collection
DiffractometerOxford Diffraction Gemini R
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.909, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
8038, 1777, 1657
Rint0.017
(sin θ/λ)max1)0.648
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.076, 1.18
No. of reflections1777
No. of parameters218
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.14

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis PRO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O1i0.872.082.901 (2)158.2
C5—H5A···O1i0.942.543.436 (2)158.8
Symmetry code: (i) x1/2, y+1/2, z1/2.
 

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