4-Chloro-6-methyl-N-(4-methyl-phen-yl)quinolin-2-amine.

In the title compound C(17)H(15)ClN(2), the dihedral angle between the quinoline ring system and the phenyl ring is 50.18 (6)°. In the crystal, mol-ecules are linked into chains running along the c axis by N-H⋯N hydrogen bonds.

Related literature

For the biological activity of quinoline derivatives, see: Lunniss et al. (2009 ▶); Kemnitzer et al. (2008 ▶); Woodrow et al. (2009 ▶). For a related structure, see: Cheng et al. (2005 ▶). For the synthesis, see: Manoj et al. (2011 ▶).

Experimental

Crystal data

C17H15ClN2

M = 282.76

Monoclinic,

a = 15.1445 (13) Å

b = 11.4337 (10) Å

c = 8.4764 (7) Å

β = 92.344 (4)°

V = 1466.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.22 × 0.21 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

13649 measured reflections

3669 independent reflections

2508 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.125

S = 1.03

3669 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAIn class="Chemical">NT; 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: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811002327/bt5456sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002327/bt5456Isup2.hkl

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

C17H15ClN2	F(000) = 592
Mr = 282.76	Dx = 1.281 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3683 reflections
a = 15.1445 (13) Å	θ = 1.3–28.4°
b = 11.4337 (10) Å	µ = 0.25 mm−1
c = 8.4764 (7) Å	T = 293 K
β = 92.344 (4)°	Block, yellow
V = 1466.5 (2) Å3	0.22 × 0.21 × 0.20 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	2508 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
graphite	θmax = 28.4°, θmin = 1.4°
ω and φ scans	h = −17→20
13649 measured reflections	k = −13→15
3669 independent reflections	l = −11→11

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.052P)2 + 0.3324P] where P = (Fo2 + 2Fc2)/3
3669 reflections	(Δ/σ)max = 0.001
183 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.88432 (3)	0.45826 (5)	0.04769 (5)	0.07158 (19)
C4	0.83107 (10)	0.48222 (13)	−0.26320 (17)	0.0457 (4)
N1	0.70049 (9)	0.37817 (12)	−0.37362 (14)	0.0493 (3)
C5	0.77053 (10)	0.45280 (13)	−0.38898 (17)	0.0452 (3)
C6	0.78424 (12)	0.50298 (17)	−0.53791 (19)	0.0571 (4)
H6	0.7459	0.4847	−0.6228	0.068*
C3	0.90078 (11)	0.55972 (15)	−0.2897 (2)	0.0537 (4)
H3	0.9400	0.5786	−0.2063	0.064*
C8	0.81569 (11)	0.42723 (14)	−0.11597 (17)	0.0490 (4)
C9	0.74846 (12)	0.35319 (15)	−0.10002 (19)	0.0545 (4)
H9	0.7394	0.3172	−0.0036	0.065*
N2	0.62355 (11)	0.25326 (14)	−0.21237 (17)	0.0660 (4)
H2	0.6281	0.2093	−0.1301	0.079*
C7	0.85260 (12)	0.57759 (16)	−0.5596 (2)	0.0610 (5)
H7	0.8599	0.6092	−0.6593	0.073*
C2	0.91267 (12)	0.60825 (16)	−0.4350 (2)	0.0578 (4)
C11	0.54756 (13)	0.23837 (16)	−0.3114 (2)	0.0585 (4)
C10	0.69089 (11)	0.33048 (14)	−0.23354 (19)	0.0509 (4)
C16	0.50425 (12)	0.33144 (16)	−0.3851 (2)	0.0633 (5)
H16	0.5279	0.4063	−0.3755	0.076*
C14	0.38882 (13)	0.2042 (2)	−0.4889 (2)	0.0721 (6)
C15	0.42658 (13)	0.31429 (18)	−0.4723 (2)	0.0691 (5)
H15	0.3988	0.3780	−0.5213	0.083*
C12	0.51110 (15)	0.12859 (18)	−0.3286 (2)	0.0754 (6)
H12	0.5393	0.0646	−0.2812	0.091*
C1	0.98772 (14)	0.69163 (19)	−0.4625 (3)	0.0794 (6)
H1A	0.9647	0.7693	−0.4775	0.119*
H1B	1.0178	0.6680	−0.5549	0.119*
H1C	1.0284	0.6907	−0.3727	0.119*
C17	0.30336 (15)	0.1871 (2)	−0.5837 (3)	0.1002 (8)
H17A	0.3034	0.1115	−0.6330	0.150*
H17B	0.2977	0.2465	−0.6635	0.150*
H17C	0.2546	0.1923	−0.5152	0.150*
C13	0.43288 (16)	0.1126 (2)	−0.4157 (3)	0.0818 (7)
H13	0.4093	0.0377	−0.4251	0.098*

	U11	U22	U33	U12	U13	U23
Cl1	0.0732 (3)	0.0915 (4)	0.0487 (3)	0.0072 (3)	−0.0138 (2)	0.0015 (2)
C4	0.0506 (8)	0.0431 (8)	0.0435 (8)	0.0052 (7)	0.0014 (6)	−0.0006 (6)
N1	0.0576 (8)	0.0490 (7)	0.0415 (7)	−0.0057 (6)	0.0054 (6)	−0.0029 (6)
C5	0.0513 (8)	0.0439 (8)	0.0406 (7)	−0.0002 (7)	0.0037 (6)	−0.0011 (6)
C6	0.0644 (10)	0.0655 (11)	0.0411 (8)	−0.0082 (9)	−0.0010 (7)	0.0034 (8)
C3	0.0536 (9)	0.0528 (10)	0.0542 (9)	−0.0011 (8)	−0.0037 (7)	−0.0015 (8)
C8	0.0565 (9)	0.0508 (9)	0.0395 (8)	0.0090 (8)	−0.0011 (7)	−0.0007 (7)
C9	0.0697 (11)	0.0531 (10)	0.0410 (8)	0.0055 (9)	0.0069 (7)	0.0060 (7)
N2	0.0813 (10)	0.0610 (9)	0.0561 (9)	−0.0195 (8)	0.0079 (8)	0.0082 (7)
C7	0.0694 (11)	0.0659 (12)	0.0483 (9)	−0.0085 (9)	0.0076 (8)	0.0112 (8)
C2	0.0571 (9)	0.0523 (10)	0.0641 (11)	−0.0037 (8)	0.0049 (8)	0.0028 (8)
C11	0.0720 (11)	0.0512 (10)	0.0540 (9)	−0.0145 (9)	0.0211 (8)	−0.0070 (8)
C10	0.0622 (10)	0.0443 (9)	0.0469 (9)	−0.0012 (8)	0.0106 (7)	−0.0016 (7)
C16	0.0644 (11)	0.0509 (11)	0.0759 (12)	−0.0124 (9)	0.0198 (9)	−0.0141 (9)
C14	0.0716 (12)	0.0801 (14)	0.0660 (12)	−0.0248 (11)	0.0220 (10)	−0.0215 (11)
C15	0.0644 (11)	0.0662 (13)	0.0780 (13)	−0.0061 (9)	0.0198 (10)	−0.0078 (10)
C12	0.0959 (15)	0.0530 (11)	0.0781 (13)	−0.0185 (11)	0.0119 (11)	−0.0002 (10)
C1	0.0747 (13)	0.0750 (14)	0.0886 (15)	−0.0199 (11)	0.0065 (11)	0.0112 (11)
C17	0.0856 (16)	0.121 (2)	0.0946 (17)	−0.0340 (15)	0.0107 (13)	−0.0253 (16)
C13	0.0992 (17)	0.0598 (13)	0.0876 (15)	−0.0334 (12)	0.0173 (13)	−0.0139 (11)

Cl1—C8	1.7356 (16)	C2—C1	1.509 (3)
C4—C3	1.403 (2)	C11—C12	1.377 (3)
C4—C5	1.418 (2)	C11—C16	1.385 (3)
C4—C8	1.425 (2)	C16—C15	1.378 (3)
N1—C10	1.320 (2)	C16—H16	0.9300
N1—C5	1.3716 (19)	C14—C13	1.376 (3)
C5—C6	1.410 (2)	C14—C15	1.387 (3)
C6—C7	1.360 (2)	C14—C17	1.508 (3)
C6—H6	0.9300	C15—H15	0.9300
C3—C2	1.369 (2)	C12—C13	1.382 (3)
C3—H3	0.9300	C12—H12	0.9300
C8—C9	1.335 (2)	C1—H1A	0.9600
C9—C10	1.424 (2)	C1—H1B	0.9600
C9—H9	0.9300	C1—H1C	0.9600
N2—C10	1.366 (2)	C17—H17A	0.9600
N2—C11	1.407 (2)	C17—H17B	0.9600
N2—H2	0.8600	C17—H17C	0.9600
C7—C2	1.410 (2)	C13—H13	0.9300
C7—H7	0.9300
C3—C4—C5	119.79 (14)	N1—C10—N2	119.69 (15)
C3—C4—C8	124.74 (14)	N1—C10—C9	123.58 (15)
C5—C4—C8	115.47 (14)	N2—C10—C9	116.71 (15)
C10—N1—C5	117.16 (13)	C15—C16—C11	120.72 (17)
N1—C5—C6	118.75 (14)	C15—C16—H16	119.6
N1—C5—C4	123.71 (13)	C11—C16—H16	119.6
C6—C5—C4	117.54 (14)	C13—C14—C15	117.0 (2)
C7—C6—C5	121.16 (15)	C13—C14—C17	122.1 (2)
C7—C6—H6	119.4	C15—C14—C17	120.8 (2)
C5—C6—H6	119.4	C16—C15—C14	121.5 (2)
C2—C3—C4	121.83 (15)	C16—C15—H15	119.2
C2—C3—H3	119.1	C14—C15—H15	119.2
C4—C3—H3	119.1	C11—C12—C13	120.5 (2)
C9—C8—C4	121.40 (14)	C11—C12—H12	119.7
C9—C8—Cl1	118.87 (12)	C13—C12—H12	119.7
C4—C8—Cl1	119.72 (13)	C2—C1—H1A	109.5
C8—C9—C10	118.67 (14)	C2—C1—H1B	109.5
C8—C9—H9	120.7	H1A—C1—H1B	109.5
C10—C9—H9	120.7	C2—C1—H1C	109.5
C10—N2—C11	126.62 (15)	H1A—C1—H1C	109.5
C10—N2—H2	116.7	H1B—C1—H1C	109.5
C11—N2—H2	116.7	C14—C17—H17A	109.5
C6—C7—C2	121.75 (16)	C14—C17—H17B	109.5
C6—C7—H7	119.1	H17A—C17—H17B	109.5
C2—C7—H7	119.1	C14—C17—H17C	109.5
C3—C2—C7	117.93 (16)	H17A—C17—H17C	109.5
C3—C2—C1	121.50 (17)	H17B—C17—H17C	109.5
C7—C2—C1	120.56 (17)	C14—C13—C12	121.99 (19)
C12—C11—C16	118.19 (19)	C14—C13—H13	119.0
C12—C11—N2	119.22 (19)	C12—C13—H13	119.0
C16—C11—N2	122.46 (16)
C10—N1—C5—C6	178.35 (15)	C6—C7—C2—C1	−179.77 (18)
C10—N1—C5—C4	−1.1 (2)	C10—N2—C11—C12	146.26 (19)
C3—C4—C5—N1	−179.84 (14)	C10—N2—C11—C16	−38.0 (3)
C8—C4—C5—N1	0.9 (2)	C5—N1—C10—N2	−178.42 (15)
C3—C4—C5—C6	0.7 (2)	C5—N1—C10—C9	0.4 (2)
C8—C4—C5—C6	−178.59 (15)	C11—N2—C10—N1	−17.5 (3)
N1—C5—C6—C7	179.95 (16)	C11—N2—C10—C9	163.54 (16)
C4—C5—C6—C7	−0.5 (3)	C8—C9—C10—N1	0.4 (3)
C5—C4—C3—C2	−0.2 (3)	C8—C9—C10—N2	179.33 (15)
C8—C4—C3—C2	178.95 (16)	C12—C11—C16—C15	0.3 (3)
C3—C4—C8—C9	−179.17 (16)	N2—C11—C16—C15	−175.44 (16)
C5—C4—C8—C9	0.0 (2)	C11—C16—C15—C14	0.4 (3)
C3—C4—C8—Cl1	1.9 (2)	C13—C14—C15—C16	−0.7 (3)
C5—C4—C8—Cl1	−178.91 (11)	C17—C14—C15—C16	179.50 (18)
C4—C8—C9—C10	−0.7 (2)	C16—C11—C12—C13	−0.7 (3)
Cl1—C8—C9—C10	178.30 (12)	N2—C11—C12—C13	175.21 (18)
C5—C6—C7—C2	0.0 (3)	C15—C14—C13—C12	0.3 (3)
C4—C3—C2—C7	−0.4 (3)	C17—C14—C13—C12	−179.9 (2)
C4—C3—C2—C1	179.92 (17)	C11—C12—C13—C14	0.4 (3)
C6—C7—C2—C3	0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1i	0.86	2.59	3.404 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1i	0.86	2.59	3.404 (2)	157

Symmetry code: (i) .