4-Chloro-2,5-dimethyl-quinoline.

Mol-ecules of the title compound, C(11)H(10)ClN, are essentially planar (r.m.s. deviation for all non-H atoms = 0.009 Å) and are stacked along the a axis with the centroids of the benzene and pyridine rings alternately separated by 3.649 (1) and 3.778 (1) Å.

Related literature

For the biological activity of quinoline derivatives, see: Miyamoto et al. (1995 ▶); Milner et al. (2010 ▶); Li et al. (2008 ▶); Musiola et al. (2006 ▶); Muthumani et al. (2010 ▶). For related chloro­quinoline structures, see: Rizvi et al. (2008 ▶); Bureau et al. (1999 ▶); de Souza et al. (2010 ▶); Yathirajan et al. (2007 ▶).

Experimental

Crystal data

C11H10ClN

M = 190.66

Monoclinic,

a = 6.9534 (9) Å

b = 13.0762 (14) Å

c = 10.4306 (11) Å

β = 99.239 (8)°

V = 936.09 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 293 K

0.27 × 0.26 × 0.22 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.909, T max = 0.925

8798 measured reflections

2345 independent reflections

1502 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.147

S = 1.05

2345 reflections

120 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810025419/ci5114sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025419/ci5114Isup2.hkl

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

C11H10ClN	F(000) = 400
Mr = 190.66	Dx = 1.353 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2345 reflections
a = 6.9534 (9) Å	θ = 2.5–28.5°
b = 13.0762 (14) Å	µ = 0.35 mm−1
c = 10.4306 (11) Å	T = 293 K
β = 99.239 (8)°	Block, colourless
V = 936.09 (19) Å3	0.27 × 0.26 × 0.22 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	2345 independent reflections
Radiation source: fine-focus sealed tube	1502 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω and φ scans	θmax = 28.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→9
Tmin = 0.909, Tmax = 0.925	k = −17→12
8798 measured reflections	l = −13→10

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0468P)2 + 0.6973P] where P = (Fo2 + 2Fc2)/3
2345 reflections	(Δ/σ)max = 0.007
120 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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	0.27505 (13)	0.22264 (5)	0.06695 (7)	0.0680 (3)
N1	0.2186 (3)	−0.08447 (15)	−0.13203 (18)	0.0455 (5)
C5	0.2644 (3)	0.01002 (16)	0.0758 (2)	0.0372 (5)
C8	0.2282 (4)	0.09687 (19)	−0.1312 (2)	0.0461 (6)
H8	0.2218	0.1571	−0.1791	0.055*
C9	0.2550 (4)	0.10065 (17)	0.0003 (2)	0.0410 (5)
C1	0.2513 (4)	−0.17776 (18)	0.0632 (2)	0.0485 (6)
H1	0.2379	−0.2374	0.0140	0.058*
C6	0.2455 (3)	−0.08204 (17)	0.0005 (2)	0.0383 (5)
C3	0.2963 (4)	−0.0945 (2)	0.2683 (2)	0.0504 (6)
H3	0.3140	−0.1002	0.3583	0.060*
C10	0.1806 (5)	−0.0015 (2)	−0.3412 (2)	0.0622 (8)
H10A	0.1524	−0.0705	−0.3697	0.093*
H10B	0.2969	0.0213	−0.3712	0.093*
H10C	0.0738	0.0420	−0.3760	0.093*
C4	0.2913 (4)	0.00173 (18)	0.2147 (2)	0.0426 (5)
C7	0.2103 (4)	0.00246 (19)	−0.1951 (2)	0.0443 (6)
C11	0.3095 (5)	0.0919 (2)	0.3066 (2)	0.0629 (8)
H11A	0.3289	0.0677	0.3946	0.094*
H11B	0.1926	0.1321	0.2905	0.094*
H11C	0.4186	0.1332	0.2931	0.094*
C2	0.2761 (4)	−0.18365 (19)	0.1949 (2)	0.0529 (7)
H2	0.2796	−0.2470	0.2356	0.064*

	U11	U22	U33	U12	U13	U23
Cl1	0.1124 (7)	0.0347 (3)	0.0570 (4)	−0.0066 (4)	0.0141 (4)	−0.0037 (3)
N1	0.0560 (13)	0.0426 (11)	0.0382 (10)	0.0017 (9)	0.0092 (9)	−0.0031 (8)
C5	0.0383 (12)	0.0372 (11)	0.0365 (11)	0.0000 (10)	0.0076 (9)	−0.0003 (9)
C8	0.0556 (16)	0.0430 (13)	0.0403 (13)	−0.0010 (11)	0.0094 (11)	0.0077 (10)
C9	0.0480 (14)	0.0338 (11)	0.0417 (12)	−0.0024 (10)	0.0082 (10)	−0.0006 (9)
C1	0.0601 (17)	0.0341 (11)	0.0520 (14)	0.0037 (11)	0.0106 (12)	0.0004 (10)
C6	0.0406 (13)	0.0375 (11)	0.0370 (11)	0.0026 (9)	0.0068 (9)	−0.0004 (9)
C3	0.0599 (16)	0.0566 (15)	0.0349 (12)	0.0031 (13)	0.0086 (11)	0.0099 (11)
C10	0.077 (2)	0.0737 (19)	0.0356 (13)	−0.0033 (16)	0.0085 (13)	0.0012 (12)
C4	0.0484 (14)	0.0439 (12)	0.0360 (12)	−0.0023 (10)	0.0085 (10)	−0.0012 (9)
C7	0.0497 (15)	0.0483 (13)	0.0349 (12)	−0.0005 (11)	0.0070 (10)	0.0008 (10)
C11	0.094 (2)	0.0591 (16)	0.0353 (13)	−0.0126 (15)	0.0096 (13)	−0.0094 (12)
C2	0.0654 (18)	0.0398 (12)	0.0545 (15)	0.0082 (12)	0.0121 (13)	0.0137 (11)

Cl1—C9	1.737 (2)	C3—C4	1.374 (3)
N1—C7	1.310 (3)	C3—C2	1.390 (4)
N1—C6	1.366 (3)	C3—H3	0.93
C5—C9	1.419 (3)	C10—C7	1.506 (3)
C5—C6	1.432 (3)	C10—H10A	0.96
C5—C4	1.435 (3)	C10—H10B	0.96
C8—C9	1.356 (3)	C10—H10C	0.96
C8—C7	1.399 (3)	C4—C11	1.512 (3)
C8—H8	0.93	C11—H11A	0.96
C1—C2	1.358 (3)	C11—H11B	0.96
C1—C6	1.410 (3)	C11—H11C	0.96
C1—H1	0.93	C2—H2	0.93
C7—N1—C6	118.4 (2)	C7—C10—H10B	109.5
C9—C5—C6	114.0 (2)	H10A—C10—H10B	109.5
C9—C5—C4	127.6 (2)	C7—C10—H10C	109.5
C6—C5—C4	118.4 (2)	H10A—C10—H10C	109.5
C9—C8—C7	120.1 (2)	H10B—C10—H10C	109.5
C9—C8—H8	120.0	C3—C4—C5	118.0 (2)
C7—C8—H8	120.0	C3—C4—C11	117.5 (2)
C8—C9—C5	121.2 (2)	C5—C4—C11	124.4 (2)
C8—C9—Cl1	115.32 (18)	N1—C7—C8	122.2 (2)
C5—C9—Cl1	123.49 (18)	N1—C7—C10	117.8 (2)
C2—C1—C6	120.6 (2)	C8—C7—C10	120.0 (2)
C2—C1—H1	119.7	C4—C11—H11A	109.5
C6—C1—H1	119.7	C4—C11—H11B	109.5
N1—C6—C1	116.0 (2)	H11A—C11—H11B	109.5
N1—C6—C5	124.1 (2)	C4—C11—H11C	109.5
C1—C6—C5	119.9 (2)	H11A—C11—H11C	109.5
C4—C3—C2	123.4 (2)	H11B—C11—H11C	109.5
C4—C3—H3	118.3	C1—C2—C3	119.6 (2)
C2—C3—H3	118.3	C1—C2—H2	120.2
C7—C10—H10A	109.5	C3—C2—H2	120.2
C7—C8—C9—C5	−0.3 (4)	C4—C5—C6—C1	0.8 (3)
C7—C8—C9—Cl1	180.0 (2)	C2—C3—C4—C5	−0.2 (4)
C6—C5—C9—C8	0.7 (3)	C2—C3—C4—C11	178.3 (3)
C4—C5—C9—C8	−179.8 (2)	C9—C5—C4—C3	−179.9 (2)
C6—C5—C9—Cl1	−179.65 (18)	C6—C5—C4—C3	−0.4 (3)
C4—C5—C9—Cl1	−0.1 (4)	C9—C5—C4—C11	1.7 (4)
C7—N1—C6—C1	179.4 (2)	C6—C5—C4—C11	−178.8 (2)
C7—N1—C6—C5	0.4 (3)	C6—N1—C7—C8	0.1 (4)
C2—C1—C6—N1	−179.6 (2)	C6—N1—C7—C10	180.0 (2)
C2—C1—C6—C5	−0.5 (4)	C9—C8—C7—N1	−0.1 (4)
C9—C5—C6—N1	−0.7 (3)	C9—C8—C7—C10	−180.0 (2)
C4—C5—C6—N1	179.7 (2)	C6—C1—C2—C3	−0.1 (4)
C9—C5—C6—C1	−179.7 (2)	C4—C3—C2—C1	0.5 (4)