1-Phenyl-2-trifluoro­methyl-4-quinolone

Hossaini Sadr, M.; Usachev, B.I.; Shan, G.; Ng, S.W.

doi:10.1107/S1600536807062939

organic compounds

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Volume 64| Part 1| January 2008| Page o180

https://doi.org/10.1107/S1600536807062939

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1-Phenyl-2-trifluoromethyl-4-quinolone

Moayad Hossaini Sadr,^a Boris I. Usachev,^b Gao Shan ^c and Seik Weng Ng ^d ^*

^aDepartment of Chemistry, Azarbaijan University of Tarbiat Moallem, Tabriz, Iran, ^bDepartment of Chemistry, Ural State University, Lenina Prospekt 51, 620083 Ekaterinburg, Russian Federation, ^cSchool of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 22 November 2007; accepted 24 November 2007; online 6 December 2007)

In the title molecule, C₁₆H₁₀F₃NO, the N-bound phenyl ring is oriented nearly orthogonal to the quinolinyl ring in order to avoid steric clashes with the trifluoromethyl substituent [dihedral angle 89.7 (1)°].

Related literature

For synthesis, see: Sosnovskikh et al. (2005 ); Usachev & Sosnovskikh (2004 ).

Experimental

Crystal data

C₁₆H₁₀F₃NO
M_r = 289.25
Monoclinic, P 2₁ /c
a = 8.7403 (5) Å
b = 17.574 (1) Å
c = 8.7559 (6) Å
β = 103.931 (2)°
V = 1305.4 (1) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 295 (2) K
0.35 × 0.25 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.843, T_max = 0.982
20310 measured reflections
2970 independent reflections
1882 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.147
S = 1.14
2970 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: RAPID-AUTO (Rigaku Corporation, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807062939/tk2227sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062939/tk2227Isup2.hkl

checkCIF report

Comment top

Compound (I) was isolated during an attempted reaction of the corresponding thione with CuCl₂ in THF solution, see Experimental. The N-bound aromatic ring in (I) occupies a position orthogonal to the quinolinyl ring so as to avoid steric clashes with the adjacent CF₃ group, Fig. 1.

Related literature top

For synthesis, see: Sosnovskikh et al. (2005); Usachev & Sosnovskikh (2004).

Experimental top

The synthesis of (I) has been described by Usachev & Sosnovskikh (2004); also see Sosnovskikh et al. (2005). In the present study, (I) was obtained as a side-product when the thione was recrystallized from THF in the presence of copper(II) chloride.

Structure description top

For synthesis, see: Sosnovskikh et al. (2005); Usachev & Sosnovskikh (2004).

Computing details top

Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO (Rigaku Corporation, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

Fig. 1. Molecular structure of (I) showing displacement ellipsoids at the 50% probability level and H atoms as spheres of arbitrary radius.

1-Phenyl-2-trifluoromethyl-4-quinolone top

Crystal data top

C₁₆H₁₀F₃NO	F(000) = 592
M_r = 289.25	D_x = 1.472 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12413 reflections
a = 8.7403 (5) Å	θ = 3.2–27.5°
b = 17.574 (1) Å	µ = 0.12 mm⁻¹
c = 8.7559 (6) Å	T = 295 K
β = 103.931 (2)°	Prism, yellow
V = 1305.4 (1) Å³	0.35 × 0.25 × 0.15 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	2970 independent reflections
Radiation source: fine-focus sealed tube	1882 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 10.000 pixels mm^-1	θ_max = 27.4°, θ_min = 3.2°
ω scans	h = −11→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −22→22
T_min = 0.843, T_max = 0.982	l = −11→11
20310 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.147	w = 1/[σ²(F_o²) + (0.0722P)² + 0.1288P] where P = (F_o² + 2F_c²)/3
S = 1.14	(Δ/σ)_max = 0.001
2970 reflections	Δρ_max = 0.22 e Å⁻³
191 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.005 (3)

Crystal data top

C₁₆H₁₀F₃NO	V = 1305.4 (1) Å³
M_r = 289.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.7403 (5) Å	µ = 0.12 mm⁻¹
b = 17.574 (1) Å	T = 295 K
c = 8.7559 (6) Å	0.35 × 0.25 × 0.15 mm
β = 103.931 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2970 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1882 reflections with I > 2σ(I)
T_min = 0.843, T_max = 0.982	R_int = 0.030
20310 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.147	H-atom parameters constrained
S = 1.14	Δρ_max = 0.22 e Å⁻³
2970 reflections	Δρ_min = −0.23 e Å⁻³
191 parameters

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

	x	y	z	U_iso*/U_eq
F1	0.43638 (17)	0.24350 (8)	0.2257 (2)	0.1064 (6)
F2	0.43881 (16)	0.34786 (9)	0.10584 (14)	0.0941 (5)
F3	0.65236 (14)	0.30060 (9)	0.23970 (17)	0.0969 (5)
O1	0.72788 (16)	0.43177 (9)	0.73522 (17)	0.0794 (5)
N1	0.33546 (14)	0.36764 (7)	0.39971 (15)	0.0456 (3)
C1	0.6081 (2)	0.41335 (10)	0.6337 (2)	0.0560 (5)
C2	0.4482 (2)	0.42888 (9)	0.65010 (19)	0.0496 (4)
C3	0.4245 (2)	0.46671 (12)	0.7840 (2)	0.0660 (5)
H3	0.5114	0.4821	0.8618	0.079*
C4	0.2772 (3)	0.48118 (13)	0.8018 (2)	0.0768 (6)
H4	0.2639	0.5067	0.8907	0.092*
C5	0.1465 (3)	0.45791 (13)	0.6873 (2)	0.0721 (6)
H5	0.0458	0.4676	0.7004	0.086*
C6	0.1646 (2)	0.42053 (11)	0.5544 (2)	0.0590 (5)
H6	0.0764	0.4051	0.4781	0.071*
C7	0.31618 (19)	0.40578 (9)	0.53450 (18)	0.0461 (4)
C8	0.19504 (17)	0.34533 (9)	0.28127 (19)	0.0460 (4)
C9	0.1299 (2)	0.39618 (11)	0.1639 (2)	0.0557 (4)
H9	0.1768	0.4433	0.1582	0.067*
C10	−0.0070 (2)	0.37585 (13)	0.0544 (2)	0.0655 (5)
H10	−0.0520	0.4092	−0.0264	0.079*
C11	−0.0764 (2)	0.30637 (14)	0.0650 (2)	0.0701 (6)
H11	−0.1682	0.2931	−0.0086	0.084*
C12	−0.0110 (2)	0.25642 (13)	0.1837 (3)	0.0691 (6)
H12	−0.0589	0.2097	0.1904	0.083*
C13	0.1267 (2)	0.27569 (11)	0.2936 (2)	0.0575 (5)
H13	0.1719	0.2422	0.3741	0.069*
C14	0.61571 (19)	0.37504 (10)	0.4918 (2)	0.0547 (4)
H14	0.7140	0.3646	0.4733	0.066*
C15	0.48470 (18)	0.35353 (9)	0.3836 (2)	0.0472 (4)
C16	0.5026 (2)	0.31135 (12)	0.2388 (2)	0.0626 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.1113 (11)	0.0740 (9)	0.1504 (14)	−0.0158 (7)	0.0641 (10)	−0.0509 (9)
F2	0.0938 (10)	0.1323 (13)	0.0570 (8)	0.0227 (8)	0.0197 (7)	−0.0097 (7)
F3	0.0547 (7)	0.1408 (13)	0.1002 (10)	0.0159 (7)	0.0283 (6)	−0.0278 (9)
O1	0.0612 (8)	0.0894 (10)	0.0712 (10)	−0.0143 (7)	−0.0163 (7)	−0.0032 (8)
N1	0.0397 (7)	0.0496 (7)	0.0446 (8)	0.0023 (5)	0.0043 (5)	−0.0038 (6)
C1	0.0524 (10)	0.0504 (9)	0.0553 (10)	−0.0051 (7)	−0.0062 (8)	0.0093 (8)
C2	0.0587 (10)	0.0425 (8)	0.0412 (8)	−0.0009 (7)	−0.0004 (7)	0.0039 (7)
C3	0.0828 (14)	0.0647 (12)	0.0432 (10)	−0.0016 (9)	0.0010 (9)	−0.0027 (9)
C4	0.1019 (16)	0.0793 (14)	0.0482 (11)	0.0114 (12)	0.0165 (11)	−0.0099 (10)
C5	0.0777 (13)	0.0850 (14)	0.0563 (12)	0.0204 (11)	0.0217 (10)	−0.0009 (10)
C6	0.0551 (10)	0.0703 (12)	0.0495 (10)	0.0102 (8)	0.0088 (8)	−0.0035 (9)
C7	0.0514 (9)	0.0436 (8)	0.0405 (8)	0.0058 (6)	0.0054 (7)	0.0028 (7)
C8	0.0382 (8)	0.0549 (9)	0.0427 (9)	0.0013 (6)	0.0056 (6)	−0.0053 (7)
C9	0.0509 (9)	0.0630 (11)	0.0500 (10)	0.0054 (7)	0.0057 (7)	−0.0019 (8)
C10	0.0516 (10)	0.0912 (15)	0.0481 (10)	0.0131 (10)	0.0013 (8)	−0.0037 (10)
C11	0.0439 (9)	0.1105 (18)	0.0526 (11)	−0.0076 (10)	0.0052 (8)	−0.0243 (11)
C12	0.0532 (10)	0.0841 (14)	0.0708 (13)	−0.0185 (9)	0.0163 (9)	−0.0180 (11)
C13	0.0509 (9)	0.0637 (11)	0.0569 (10)	−0.0061 (8)	0.0111 (8)	−0.0016 (8)
C14	0.0406 (9)	0.0570 (10)	0.0621 (11)	0.0011 (7)	0.0039 (7)	0.0049 (8)
C15	0.0428 (8)	0.0460 (9)	0.0510 (10)	0.0028 (6)	0.0081 (7)	0.0027 (7)
C16	0.0502 (10)	0.0700 (12)	0.0682 (12)	0.0045 (9)	0.0157 (8)	−0.0098 (10)

Geometric parameters (Å, º) top

F1—C16	1.318 (2)	C6—C7	1.402 (2)
F2—C16	1.328 (2)	C6—H6	0.9300
F3—C16	1.321 (2)	C8—C9	1.377 (2)
O1—C1	1.2421 (19)	C8—C13	1.377 (2)
N1—C15	1.368 (2)	C9—C10	1.389 (2)
N1—C7	1.402 (2)	C9—H9	0.9300
N1—C8	1.4569 (19)	C10—C11	1.376 (3)
C1—C14	1.429 (3)	C10—H10	0.9300
C1—C2	1.464 (3)	C11—C12	1.375 (3)
C2—C7	1.400 (2)	C11—H11	0.9300
C2—C3	1.405 (3)	C12—C13	1.390 (3)
C3—C4	1.358 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.388 (3)	C14—C15	1.353 (2)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.378 (3)	C15—C16	1.509 (3)
C5—H5	0.9300

C15—N1—C7	118.97 (13)	C8—C9—C10	118.76 (19)
C15—N1—C8	122.58 (13)	C8—C9—H9	120.6
C7—N1—C8	118.45 (12)	C10—C9—H9	120.6
O1—C1—C14	122.49 (18)	C11—C10—C9	120.14 (19)
O1—C1—C2	122.78 (18)	C11—C10—H10	119.9
C14—C1—C2	114.73 (14)	C9—C10—H10	119.9
C7—C2—C3	118.62 (17)	C10—C11—C12	120.51 (17)
C7—C2—C1	121.02 (16)	C10—C11—H11	119.7
C3—C2—C1	120.36 (16)	C12—C11—H11	119.7
C4—C3—C2	121.24 (18)	C11—C12—C13	120.06 (19)
C4—C3—H3	119.4	C11—C12—H12	120.0
C2—C3—H3	119.4	C13—C12—H12	120.0
C3—C4—C5	120.03 (19)	C8—C13—C12	118.78 (18)
C3—C4—H4	120.0	C8—C13—H13	120.6
C5—C4—H4	120.0	C12—C13—H13	120.6
C6—C5—C4	120.56 (19)	C15—C14—C1	122.15 (16)
C6—C5—H5	119.7	C15—C14—H14	118.9
C4—C5—H5	119.7	C1—C14—H14	118.9
C5—C6—C7	119.82 (18)	C14—C15—N1	122.97 (16)
C5—C6—H6	120.1	C14—C15—C16	118.99 (15)
C7—C6—H6	120.1	N1—C15—C16	118.04 (14)
C2—C7—N1	120.14 (15)	F1—C16—F3	106.56 (16)
C2—C7—C6	119.74 (15)	F1—C16—F2	106.15 (17)
N1—C7—C6	120.13 (14)	F3—C16—F2	106.31 (17)
C9—C8—C13	121.74 (16)	F1—C16—C15	112.65 (16)
C9—C8—N1	118.85 (15)	F3—C16—C15	111.59 (15)
C13—C8—N1	119.34 (15)	F2—C16—C15	113.10 (16)

O1—C1—C2—C7	−178.65 (16)	C13—C8—C9—C10	−0.9 (3)
C14—C1—C2—C7	1.2 (2)	N1—C8—C9—C10	−177.78 (15)
O1—C1—C2—C3	0.6 (3)	C8—C9—C10—C11	0.7 (3)
C14—C1—C2—C3	−179.60 (16)	C9—C10—C11—C12	−0.1 (3)
C7—C2—C3—C4	−0.3 (3)	C10—C11—C12—C13	−0.4 (3)
C1—C2—C3—C4	−179.56 (19)	C9—C8—C13—C12	0.5 (3)
C2—C3—C4—C5	0.6 (3)	N1—C8—C13—C12	177.32 (16)
C3—C4—C5—C6	−0.5 (3)	C11—C12—C13—C8	0.2 (3)
C4—C5—C6—C7	0.1 (3)	O1—C1—C14—C15	178.37 (17)
C3—C2—C7—N1	−179.75 (15)	C2—C1—C14—C15	−1.4 (2)
C1—C2—C7—N1	−0.5 (2)	C1—C14—C15—N1	1.1 (3)
C3—C2—C7—C6	−0.1 (3)	C1—C14—C15—C16	−178.30 (16)
C1—C2—C7—C6	179.14 (15)	C7—N1—C15—C14	−0.3 (2)
C15—N1—C7—C2	0.0 (2)	C8—N1—C15—C14	178.98 (15)
C8—N1—C7—C2	−179.28 (14)	C7—N1—C15—C16	179.08 (15)
C15—N1—C7—C6	−179.62 (15)	C8—N1—C15—C16	−1.6 (2)
C8—N1—C7—C6	1.1 (2)	C14—C15—C16—F1	120.25 (19)
C5—C6—C7—C2	0.2 (3)	N1—C15—C16—F1	−59.1 (2)
C5—C6—C7—N1	179.87 (17)	C14—C15—C16—F3	0.4 (3)
C15—N1—C8—C9	−91.06 (19)	N1—C15—C16—F3	−178.97 (16)
C7—N1—C8—C9	88.22 (19)	C14—C15—C16—F2	−119.37 (18)
C15—N1—C8—C13	92.0 (2)	N1—C15—C16—F2	61.2 (2)
C7—N1—C8—C13	−88.73 (19)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₀F₃NO
M_r	289.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	8.7403 (5), 17.574 (1), 8.7559 (6)
β (°)	103.931 (2)
V (Å³)	1305.4 (1)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.35 × 0.25 × 0.15

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.843, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	20310, 2970, 1882
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.147, 1.14
No. of reflections	2970
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.23

Computer programs: RAPID-AUTO (Rigaku Corporation, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Acknowledgements

The authors thank the Research Office of Azarbaijan University of Tarbiat Moallem, Heilongjiang Province Natural Science Foundation (grant No. B200501), the Scientific Fund for Remarkable Teachers of Heilongjiang Province (grant No. 1054 G036), Heilongjiang University, and the University of Malaya for supporting this work.

References

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Rigaku Corporation (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
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Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany. Google Scholar
Sosnovskikh, V. Ya., Usachev, B. I., Sevenard, D. V. & Roeschenthaler, G.-V. (2005). J. Fluorine Chem. 126, 779–784. Web of Science CrossRef CAS Google Scholar
Usachev, B. I. & Sosnovskikh, V. Ya. (2004). J. Fluorine Chem. 125, 1393–1395. Web of Science CrossRef CAS Google Scholar
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