6-Chloro-2-cyclo-propyl-4-(trifluoro-meth-yl)quinoline.

In the title compound, C(13)H(9)ClF(3)N, the quinoline ring system makes a dihedral angle of 88.8 (2)° with the cyclo-propyl ring.

Related literature

For general background to quinolines see: Kayser & Novak (1987 ▶); Rudin et al. (1984 ▶); Mao et al. (2009 ▶); Bermudez et al. (2004 ▶); Jayaprakash et al. (2006 ▶); Andries et al. (2005 ▶). For related structures, see: Skörska et al. (2005 ▶); Devarajegowda et al. (2010 ▶); Li et al. (2005 ▶).

Experimental

Crystal data

C13H9ClF3N

M = 271.66

Monoclinic,

a = 13.8482 (19) Å

b = 5.0534 (8) Å

c = 18.048 (3) Å

β = 107.503 (17)°

V = 1204.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 293 K

0.22 × 0.15 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010 ▶) T min = 0.942, T max = 0.961

11631 measured reflections

2105 independent reflections

946 reflections with I > 2σ(I)

R int = 0.092

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.081

S = 0.78

2105 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1993) ▶; software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811003746/wn2420sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003746/wn2420Isup2.hkl

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

C13H9ClF3N	F(000) = 552
Mr = 271.66	Dx = 1.498 Mg m−3
Monoclinic, P21/c	Melting point: 335 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.8482 (19) Å	Cell parameters from 2105 reflections
b = 5.0534 (8) Å	θ = 2.4–25.0°
c = 18.048 (3) Å	µ = 0.33 mm−1
β = 107.503 (17)°	T = 293 K
V = 1204.5 (3) Å3	Plate, colourless
Z = 4	0.22 × 0.15 × 0.12 mm

Oxford Diffraction Xcalibur diffractometer	2105 independent reflections
Radiation source: Enhance (Mo) X-ray Source	946 reflections with I > 2σ(I)
graphite	Rint = 0.092
Detector resolution: 16.0839 pixels mm-1	θmax = 25.0°, θmin = 2.4°
ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010)	k = −6→6
Tmin = 0.942, Tmax = 0.961	l = −21→21
11631 measured reflections

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) = 0.081	w = 1/[σ2(Fo2) + (0.0334P)2] where P = (Fo2 + 2Fc2)/3
S = 0.78	(Δ/σ)max = 0.004
2105 reflections	Δρmax = 0.13 e Å−3
164 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0045 (8)

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05–01–2010 CrysAlis171. NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
Cl1	0.24504 (7)	−0.53695 (16)	0.14138 (5)	0.0724 (3)
F1	0.53230 (12)	0.2294 (4)	0.43406 (12)	0.1017 (8)
F2	0.49335 (13)	0.1618 (4)	0.31203 (13)	0.0964 (7)
F3	0.49773 (12)	−0.1595 (4)	0.38888 (11)	0.0896 (7)
N9	0.15811 (17)	0.2481 (4)	0.35357 (14)	0.0463 (6)
C1	0.1215 (2)	0.4767 (6)	0.49521 (17)	0.0629 (9)
H1A	0.0846	0.3137	0.4779	0.076*
H1B	0.1300	0.5228	0.5490	0.076*
C2	0.2051 (2)	0.5449 (6)	0.46255 (18)	0.0612 (9)
H2	0.2623	0.6398	0.4980	0.073*
C3	0.1078 (2)	0.6908 (6)	0.43962 (19)	0.0695 (10)
H3A	0.1077	0.8701	0.4588	0.083*
H3B	0.0624	0.6610	0.3878	0.083*
C4	0.2319 (2)	0.3623 (5)	0.40752 (17)	0.0486 (8)
C5	0.3343 (2)	0.3113 (6)	0.41542 (17)	0.0542 (9)
H5	0.3843	0.3978	0.4540	0.065*
C6	0.3612 (2)	0.1390 (6)	0.36802 (17)	0.0463 (8)
C7	0.2855 (2)	0.0029 (5)	0.30968 (16)	0.0401 (7)
C8	0.1844 (2)	0.0691 (5)	0.30551 (16)	0.0405 (7)
C10	0.4703 (3)	0.0937 (8)	0.3759 (2)	0.0678 (10)
C11	0.3025 (2)	−0.1850 (5)	0.25749 (16)	0.0452 (8)
H11	0.3683	−0.2290	0.2591	0.054*
C12	0.2229 (2)	−0.3017 (5)	0.20490 (16)	0.0456 (8)
C13	0.1232 (2)	−0.2394 (6)	0.19959 (16)	0.0489 (8)
H13	0.0699	−0.3229	0.1630	0.059*
C14	0.1044 (2)	−0.0553 (6)	0.24840 (16)	0.0464 (8)
H14	0.0378	−0.0105	0.2442	0.056*

	U11	U22	U33	U12	U13	U23
Cl1	0.0857 (7)	0.0722 (6)	0.0640 (6)	−0.0003 (5)	0.0296 (5)	−0.0188 (5)
F1	0.0448 (12)	0.1346 (18)	0.1136 (18)	−0.0181 (12)	0.0057 (12)	−0.0505 (15)
F2	0.0542 (13)	0.148 (2)	0.1014 (19)	−0.0123 (12)	0.0445 (12)	0.0029 (14)
F3	0.0516 (12)	0.0939 (15)	0.1143 (18)	0.0143 (11)	0.0113 (11)	−0.0095 (13)
N9	0.0436 (15)	0.0528 (16)	0.0448 (16)	−0.0020 (14)	0.0165 (13)	−0.0026 (14)
C1	0.085 (3)	0.058 (2)	0.057 (2)	0.0067 (19)	0.0374 (19)	−0.0017 (19)
C2	0.049 (2)	0.071 (2)	0.066 (2)	−0.0092 (19)	0.0205 (19)	−0.024 (2)
C3	0.095 (3)	0.051 (2)	0.068 (3)	0.011 (2)	0.032 (2)	0.0001 (19)
C4	0.044 (2)	0.055 (2)	0.051 (2)	−0.0035 (17)	0.0208 (18)	−0.0058 (17)
C5	0.044 (2)	0.063 (2)	0.054 (2)	−0.0126 (17)	0.0135 (17)	−0.0157 (17)
C6	0.037 (2)	0.055 (2)	0.049 (2)	0.0002 (16)	0.0153 (17)	−0.0012 (16)
C7	0.036 (2)	0.0463 (19)	0.0404 (18)	−0.0017 (15)	0.0158 (15)	0.0033 (16)
C8	0.044 (2)	0.0452 (18)	0.0351 (18)	−0.0051 (16)	0.0169 (16)	0.0028 (15)
C10	0.051 (3)	0.078 (3)	0.077 (3)	−0.003 (2)	0.023 (2)	−0.013 (2)
C11	0.0381 (19)	0.0523 (19)	0.049 (2)	0.0010 (16)	0.0191 (17)	0.0017 (17)
C12	0.053 (2)	0.0478 (19)	0.0413 (19)	−0.0054 (17)	0.0221 (17)	−0.0045 (15)
C13	0.045 (2)	0.055 (2)	0.046 (2)	−0.0110 (17)	0.0128 (17)	−0.0012 (17)
C14	0.0364 (18)	0.056 (2)	0.048 (2)	−0.0007 (16)	0.0144 (17)	−0.0033 (17)

Cl1—C12	1.741 (3)	C4—C5	1.406 (4)
F1—C10	1.329 (3)	C5—C6	1.349 (3)
F2—C10	1.330 (4)	C5—H5	0.9300
F3—C10	1.335 (3)	C6—C7	1.420 (3)
N9—C4	1.314 (3)	C6—C10	1.492 (4)
N9—C8	1.376 (3)	C7—C11	1.406 (3)
C1—C3	1.449 (4)	C7—C8	1.419 (3)
C1—C2	1.490 (4)	C8—C14	1.413 (3)
C1—H1A	0.9700	C11—C12	1.354 (3)
C1—H1B	0.9700	C11—H11	0.9300
C2—C3	1.481 (4)	C12—C13	1.392 (3)
C2—C4	1.482 (4)	C13—C14	1.359 (3)
C2—H2	0.9800	C13—H13	0.9300
C3—H3A	0.9700	C14—H14	0.9300
C3—H3B	0.9700
C4—N9—C8	117.5 (3)	C5—C6—C10	120.2 (3)
C3—C1—C2	60.5 (2)	C7—C6—C10	119.8 (3)
C3—C1—H1A	117.7	C11—C7—C8	119.0 (3)
C2—C1—H1A	117.7	C11—C7—C6	126.1 (3)
C3—C1—H1B	117.7	C8—C7—C6	114.9 (3)
C2—C1—H1B	117.7	N9—C8—C14	117.0 (3)
H1A—C1—H1B	114.8	N9—C8—C7	124.4 (3)
C3—C2—C4	120.8 (3)	C14—C8—C7	118.6 (3)
C3—C2—C1	58.35 (19)	F1—C10—F2	106.5 (3)
C4—C2—C1	120.1 (3)	F1—C10—F3	105.9 (3)
C3—C2—H2	115.3	F2—C10—F3	105.7 (3)
C4—C2—H2	115.3	F1—C10—C6	113.0 (3)
C1—C2—H2	115.3	F2—C10—C6	112.2 (3)
C1—C3—C2	61.12 (19)	F3—C10—C6	113.0 (3)
C1—C3—H3A	117.7	C12—C11—C7	119.9 (3)
C2—C3—H3A	117.7	C12—C11—H11	120.0
C1—C3—H3B	117.7	C7—C11—H11	120.0
C2—C3—H3B	117.7	C11—C12—C13	122.1 (3)
H3A—C3—H3B	114.8	C11—C12—Cl1	119.5 (2)
N9—C4—C5	122.0 (3)	C13—C12—Cl1	118.5 (2)
N9—C4—C2	118.4 (3)	C14—C13—C12	119.3 (3)
C5—C4—C2	119.6 (3)	C14—C13—H13	120.3
C6—C5—C4	121.1 (3)	C12—C13—H13	120.3
C6—C5—H5	119.4	C13—C14—C8	121.1 (3)
C4—C5—H5	119.4	C13—C14—H14	119.5
C5—C6—C7	120.0 (3)	C8—C14—H14	119.5
C3—C1—C2—C4	−109.7 (3)	C6—C7—C8—N9	−0.6 (4)
C4—C2—C3—C1	108.6 (3)	C11—C7—C8—C14	−0.5 (4)
C8—N9—C4—C5	1.6 (4)	C6—C7—C8—C14	179.3 (2)
C8—N9—C4—C2	−176.8 (2)	C5—C6—C10—F1	2.5 (5)
C3—C2—C4—N9	−27.5 (4)	C7—C6—C10—F1	−178.5 (3)
C1—C2—C4—N9	41.4 (4)	C5—C6—C10—F2	−118.0 (3)
C3—C2—C4—C5	154.1 (3)	C7—C6—C10—F2	61.0 (4)
C1—C2—C4—C5	−137.1 (3)	C5—C6—C10—F3	122.6 (3)
N9—C4—C5—C6	−0.8 (5)	C7—C6—C10—F3	−58.3 (4)
C2—C4—C5—C6	177.6 (3)	C8—C7—C11—C12	−0.7 (4)
C4—C5—C6—C7	−0.9 (4)	C6—C7—C11—C12	179.5 (3)
C4—C5—C6—C10	178.2 (3)	C7—C11—C12—C13	0.9 (4)
C5—C6—C7—C11	−178.7 (3)	C7—C11—C12—Cl1	−179.23 (19)
C10—C6—C7—C11	2.2 (4)	C11—C12—C13—C14	0.2 (4)
C5—C6—C7—C8	1.5 (4)	Cl1—C12—C13—C14	−179.7 (2)
C10—C6—C7—C8	−177.6 (3)	C12—C13—C14—C8	−1.5 (4)
C4—N9—C8—C14	179.1 (2)	N9—C8—C14—C13	−178.4 (2)
C4—N9—C8—C7	−0.9 (4)	C7—C8—C14—C13	1.6 (4)
C11—C7—C8—N9	179.5 (2)