6-[4-Chloro-2-(trifluoro-meth-yl)phen-yl]-3-fluoro-2-methyl-pyridine.

In the title compound, C13H8ClF4N, the dihedral angle between the benzene and pyridine rings is 59.8 (3)°. In the crystal, mol-ecules are stacked in columns along the b axis through weak C-H⋯π inter-actions.

Related literature

For the biological activity of pyridine derivatives, see: Patrick & Kinsmar (1996 ▶); Hishmat et al. (1990 ▶); Doshi et al. (1999 ▶); Bhatt et al. (2001 ▶).

Experimental

Crystal data

C13H8ClF4N

M = 289.65

Monoclinic,

a = 13.1813 (7) Å

b = 4.5837 (3) Å

c = 20.4448 (11) Å

β = 92.441 (3)°

V = 1234.14 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 293 K

0.2 × 0.18 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

11077 measured reflections

3033 independent reflections

2116 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.129

S = 1.01

3033 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812046211/is5209sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046211/is5209Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046211/is5209Isup3.cml

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

C13H8ClF4N	Prism
Mr = 289.65	Dx = 1.559 Mg m−3
Monoclinic, P21/n	Melting point: 408 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 13.1813 (7) Å	Cell parameters from 2116 reflections
b = 4.5837 (3) Å	θ = 1.8–26.8°
c = 20.4448 (11) Å	µ = 0.34 mm−1
β = 92.441 (3)°	T = 293 K
V = 1234.14 (12) Å3	Prism, colourless
Z = 4	0.2 × 0.18 × 0.16 mm
F(000) = 584

Bruker APEXII CCD area-detector diffractometer	2116 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 28.3°, θmin = 1.8°
Detector resolution: 1.20 pixels mm-1	h = −17→17
multi–scan	k = −5→6
11077 measured reflections	l = −27→27
3033 independent reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0549P)2 + 0.4806P] where P = (Fo2 + 2Fc2)/3
3033 reflections	(Δ/σ)max = 0.001
173 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.30 e Å−3
0 constraints

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.

	x	y	z	Uiso*/Ueq
Cl1	0.83131 (5)	0.3848 (2)	0.03175 (3)	0.0883 (3)
F1	1.12038 (13)	1.0835 (4)	0.09837 (7)	0.0978 (6)
F2	1.18924 (9)	0.8102 (3)	0.17220 (10)	0.0964 (5)
F3	1.11540 (11)	1.2001 (3)	0.19839 (7)	0.0781 (4)
F4	1.09214 (11)	1.1818 (4)	0.46328 (6)	0.0853 (5)
N1	0.93981 (11)	1.0496 (3)	0.31763 (7)	0.0451 (3)
C1	0.87112 (13)	0.6135 (5)	0.21835 (9)	0.0528 (5)
H1	0.8368	0.5883	0.2568	0.063*
C2	0.83018 (14)	0.4976 (5)	0.16091 (9)	0.0589 (5)
H2	0.7693	0.395	0.1605	0.071*
C3	0.88083 (15)	0.5361 (5)	0.10418 (9)	0.0565 (5)
C4	0.96922 (14)	0.6939 (5)	0.10389 (9)	0.0552 (5)
H4	1.0015	0.7239	0.0649	0.066*
C5	1.01029 (13)	0.8085 (4)	0.16185 (9)	0.0472 (4)
C6	0.96206 (12)	0.7668 (4)	0.22062 (9)	0.0445 (4)
C7	1.10812 (16)	0.9742 (5)	0.15823 (11)	0.0609 (5)
C8	1.00181 (13)	0.8725 (4)	0.28603 (9)	0.0453 (4)
C9	1.09464 (14)	0.7800 (5)	0.31331 (11)	0.0587 (5)
H9	1.1349	0.6502	0.291	0.07*
C10	1.12574 (16)	0.8841 (5)	0.37399 (11)	0.0638 (6)
H10	1.1876	0.8282	0.3937	0.077*
C11	1.06333 (16)	1.0706 (5)	0.40409 (10)	0.0571 (5)
C12	0.96959 (14)	1.1523 (4)	0.37664 (9)	0.0485 (4)
C13	0.90004 (18)	1.3525 (5)	0.41073 (10)	0.0642 (6)
H13A	0.8421	1.3959	0.3823	0.096*
H13B	0.9352	1.5301	0.422	0.096*
H13C	0.8779	1.2605	0.4498	0.096*

	U11	U22	U33	U12	U13	U23
Cl1	0.0773 (4)	0.1319 (7)	0.0551 (3)	−0.0171 (4)	−0.0033 (3)	−0.0247 (4)
F1	0.1080 (12)	0.1124 (13)	0.0752 (9)	−0.0472 (10)	0.0308 (8)	0.0014 (9)
F2	0.0459 (7)	0.0725 (10)	0.1719 (16)	−0.0025 (6)	0.0166 (8)	−0.0082 (10)
F3	0.0911 (9)	0.0542 (8)	0.0897 (10)	−0.0197 (7)	0.0125 (7)	−0.0126 (7)
F4	0.0926 (10)	0.0965 (11)	0.0645 (8)	0.0001 (8)	−0.0251 (7)	−0.0226 (8)
N1	0.0467 (8)	0.0453 (8)	0.0433 (7)	0.0016 (6)	0.0034 (6)	0.0002 (6)
C1	0.0444 (9)	0.0704 (13)	0.0438 (9)	−0.0028 (9)	0.0057 (7)	0.0011 (9)
C2	0.0436 (9)	0.0797 (15)	0.0535 (11)	−0.0116 (10)	0.0012 (8)	−0.0005 (10)
C3	0.0505 (10)	0.0717 (14)	0.0471 (10)	0.0010 (10)	0.0000 (8)	−0.0079 (10)
C4	0.0539 (10)	0.0649 (13)	0.0477 (10)	0.0011 (9)	0.0122 (8)	−0.0030 (9)
C5	0.0432 (9)	0.0463 (10)	0.0526 (10)	0.0013 (8)	0.0078 (7)	−0.0038 (8)
C6	0.0410 (8)	0.0463 (10)	0.0464 (9)	0.0061 (7)	0.0032 (7)	−0.0021 (8)
C7	0.0592 (12)	0.0535 (12)	0.0710 (13)	−0.0077 (10)	0.0164 (10)	−0.0069 (11)
C8	0.0431 (9)	0.0460 (10)	0.0470 (9)	0.0014 (7)	0.0024 (7)	−0.0006 (8)
C9	0.0483 (10)	0.0615 (13)	0.0656 (12)	0.0120 (9)	−0.0042 (9)	−0.0081 (10)
C10	0.0507 (11)	0.0709 (15)	0.0684 (13)	0.0043 (10)	−0.0145 (9)	−0.0026 (11)
C11	0.0626 (12)	0.0567 (12)	0.0508 (10)	−0.0059 (10)	−0.0099 (9)	−0.0062 (9)
C12	0.0557 (10)	0.0437 (10)	0.0460 (9)	−0.0040 (8)	0.0030 (8)	0.0001 (8)
C13	0.0785 (14)	0.0619 (14)	0.0526 (11)	0.0043 (11)	0.0078 (10)	−0.0098 (10)

Cl1—C3	1.737 (2)	C5—C7	1.501 (3)
F1—C7	1.339 (3)	C6—C1	1.388 (3)
F2—C7	1.328 (3)	C6—C5	1.396 (2)
F3—C7	1.322 (2)	C8—C9	1.389 (2)
F4—C11	1.353 (2)	C8—C6	1.496 (2)
N1—C8	1.338 (2)	C9—C10	1.375 (3)
N1—C12	1.338 (2)	C9—H9	0.93
C1—C2	1.378 (3)	C10—H10	0.93
C1—H1	0.93	C11—C10	1.352 (3)
C2—H2	0.93	C11—C12	1.387 (3)
C3—C2	1.374 (3)	C12—C13	1.491 (3)
C4—C3	1.372 (3)	C13—H13A	0.96
C4—H4	0.93	C13—H13B	0.96
C5—C4	1.385 (3)	C13—H13C	0.96
C8—N1—C12	119.16 (15)	F2—C7—C5	112.85 (18)
C2—C1—C6	121.99 (17)	F1—C7—C5	111.83 (18)
C2—C1—H1	119	N1—C8—C9	122.48 (17)
C6—C1—H1	119	N1—C8—C6	115.49 (15)
C3—C2—C1	118.89 (18)	C9—C8—C6	121.94 (17)
C3—C2—H2	120.6	C10—C9—C8	118.67 (19)
C1—C2—H2	120.6	C10—C9—H9	120.7
C4—C3—C2	120.98 (18)	C8—C9—H9	120.7
C4—C3—Cl1	119.69 (15)	C11—C10—C9	117.78 (18)
C2—C3—Cl1	119.33 (16)	C11—C10—H10	121.1
C3—C4—C5	119.83 (17)	C9—C10—H10	121.1
C3—C4—H4	120.1	F4—C11—C10	119.50 (18)
C5—C4—H4	120.1	F4—C11—C12	118.13 (19)
C4—C5—C6	120.57 (17)	C10—C11—C12	122.36 (18)
C4—C5—C7	117.07 (17)	N1—C12—C11	119.46 (18)
C6—C5—C7	122.37 (17)	N1—C12—C13	118.39 (17)
C1—C6—C5	117.69 (17)	C11—C12—C13	122.15 (18)
C1—C6—C8	117.57 (16)	C12—C13—H13A	109.5
C5—C6—C8	124.74 (16)	C12—C13—H13B	109.5
F3—C7—F2	105.85 (18)	H13A—C13—H13B	109.5
F3—C7—F1	105.45 (18)	C12—C13—H13C	109.5
F2—C7—F1	106.32 (18)	H13A—C13—H13C	109.5
F3—C7—C5	113.91 (17)	H13B—C13—H13C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···Cg1i	0.96	2.83	3.606 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C8–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13B⋯Cg1i	0.96	2.83	3.606 (2)	138

Symmetry code: (i) .