2-(4-Chloro-phen-yl)-6-methyl-4-(3-methyl-phen-yl)quinoline.

In the title compound, C(23)H(18)ClN, the dihedral angles between the quinoline unit and the chloro-benzene and methyl-benzene rings are 2.57 (9) and 56.06 (9)°, respectively. The crystal structure is stabilized by π-π inter-actions [minimum ring centroid separation = 3.733 (2) Å].

Related literature

For quinolines, see: Michael (1997 ▶); Balasubramanian et al. (1996 ▶). For a related structure, see: Asiri et al. (2011 ▶).

Experimental

Crystal data

C23H18ClN

M = 343.83

Monoclinic,

a = 7.982 (3) Å

b = 17.921 (6) Å

c = 12.478 (4) Å

β = 92.581 (6)°

V = 1783.1 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 293 K

0.23 × 0.22 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur CCD diffractometer

16998 measured reflections

3392 independent reflections

2508 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.168

S = 1.04

3392 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812043954/zs2238sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043954/zs2238Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043954/zs2238Isup3.cml

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

C23H18ClN	F(000) = 720
Mr = 343.83	Dx = 1.281 Mg m−3
Monoclinic, P21/c	Melting point = 371–373 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.982 (3) Å	Cell parameters from 3392 reflections
b = 17.921 (6) Å	θ = 2.0–25.7°
c = 12.478 (4) Å	µ = 0.22 mm−1
β = 92.581 (6)°	T = 293 K
V = 1783.1 (11) Å3	Block, yellow
Z = 4	0.23 × 0.22 × 0.22 mm

Oxford Diffraction Xcalibur CCD diffractometer	2508 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
Graphite monochromator	θmax = 25.7°, θmin = 2.0°
Detector resolution: 16.0839 pixels mm-1	h = −9→9
ω scans	k = −21→21
16998 measured reflections	l = −15→15
3392 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0922P)2 + 0.5751P] P = (Fo2 + 2Fc2)/3
3392 reflections	(Δ/σ)max = 0.001
228 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.89231 (10)	1.22893 (5)	0.85463 (6)	0.0816 (3)
N1	1.2557 (2)	0.97450 (10)	0.55301 (13)	0.0406 (6)
C1	0.9786 (3)	1.17421 (15)	0.7563 (2)	0.0542 (8)
C2	0.9969 (4)	1.20263 (15)	0.6569 (2)	0.0640 (9)
C3	1.0682 (4)	1.15951 (14)	0.5796 (2)	0.0607 (9)
C4	1.1224 (3)	1.08789 (12)	0.60147 (17)	0.0404 (7)
C5	1.0989 (3)	1.06052 (14)	0.70260 (18)	0.0510 (8)
C6	1.0278 (3)	1.10238 (15)	0.7802 (2)	0.0590 (9)
C7	1.2017 (2)	1.04084 (11)	0.52008 (17)	0.0387 (6)
C8	1.2226 (3)	1.06583 (11)	0.41476 (17)	0.0411 (6)
C9	1.2984 (3)	1.02293 (11)	0.34173 (16)	0.0380 (6)
C10	1.3536 (2)	0.95017 (11)	0.37377 (16)	0.0369 (6)
C11	1.4245 (3)	0.89791 (11)	0.30488 (18)	0.0413 (7)
C12	1.4739 (3)	0.82860 (11)	0.33979 (19)	0.0451 (7)
C13	1.4533 (3)	0.81027 (12)	0.44755 (19)	0.0512 (8)
C14	1.3836 (3)	0.85844 (12)	0.51636 (19)	0.0486 (7)
C15	1.3289 (2)	0.92982 (11)	0.48076 (16)	0.0379 (6)
C16	1.3247 (3)	1.05256 (11)	0.23256 (16)	0.0417 (7)
C17	1.1911 (3)	1.08107 (13)	0.17090 (18)	0.0523 (8)
C18	1.2162 (4)	1.10960 (14)	0.0705 (2)	0.0630 (10)
C19	1.3729 (4)	1.11009 (13)	0.03096 (19)	0.0639 (9)
C20	1.5098 (4)	1.08379 (13)	0.0910 (2)	0.0555 (8)
C21	1.4827 (3)	1.05492 (11)	0.19201 (18)	0.0467 (7)
C22	1.6837 (4)	1.08762 (18)	0.0504 (3)	0.0827 (11)
C23	1.5477 (4)	0.77324 (13)	0.2648 (2)	0.0612 (9)
H2	0.96150	1.25100	0.64090	0.0770*
H3	1.07990	1.17910	0.51130	0.0730*
H5	1.13240	1.01200	0.71880	0.0610*
H6	1.01310	1.08260	0.84800	0.0710*
H8	1.18350	1.11290	0.39470	0.0490*
H11	1.43820	0.91080	0.23360	0.0500*
H13	1.48850	0.76370	0.47260	0.0610*
H14	1.37150	0.84460	0.58740	0.0580*
H17	1.08400	1.08090	0.19740	0.0630*
H18	1.12600	1.12860	0.02940	0.0750*
H19	1.38760	1.12850	−0.03770	0.0770*
H21	1.57340	1.03670	0.23350	0.0560*
H22A	1.75030	1.04790	0.08160	0.1240*
H22B	1.73340	1.13470	0.06980	0.1240*
H22C	1.67850	1.08260	−0.02630	0.1240*
H23A	1.47600	0.73030	0.25820	0.0920*
H23B	1.65660	0.75820	0.29280	0.0920*
H23C	1.55780	0.79580	0.19560	0.0920*

	U11	U22	U33	U12	U13	U23
Cl1	0.0855 (6)	0.0839 (6)	0.0764 (5)	0.0060 (4)	0.0149 (4)	−0.0363 (4)
N1	0.0447 (10)	0.0354 (9)	0.0415 (10)	−0.0025 (8)	0.0002 (8)	0.0039 (7)
C1	0.0449 (13)	0.0615 (16)	0.0562 (14)	−0.0035 (11)	0.0027 (11)	−0.0205 (12)
C2	0.0766 (18)	0.0471 (14)	0.0690 (17)	0.0126 (13)	0.0111 (14)	−0.0059 (13)
C3	0.0819 (19)	0.0481 (14)	0.0527 (14)	0.0151 (13)	0.0097 (13)	0.0048 (11)
C4	0.0347 (11)	0.0415 (12)	0.0448 (12)	−0.0022 (9)	−0.0009 (9)	−0.0023 (9)
C5	0.0576 (14)	0.0497 (13)	0.0457 (13)	0.0044 (11)	0.0039 (10)	0.0013 (10)
C6	0.0653 (16)	0.0642 (16)	0.0477 (13)	0.0006 (13)	0.0060 (12)	−0.0022 (11)
C7	0.0359 (11)	0.0364 (11)	0.0433 (11)	−0.0029 (8)	−0.0032 (9)	0.0012 (9)
C8	0.0463 (12)	0.0325 (10)	0.0441 (11)	0.0039 (9)	−0.0012 (9)	0.0032 (9)
C9	0.0396 (11)	0.0340 (10)	0.0401 (11)	−0.0022 (9)	−0.0026 (9)	0.0023 (8)
C10	0.0356 (11)	0.0307 (10)	0.0438 (11)	−0.0037 (8)	−0.0036 (8)	0.0026 (8)
C11	0.0454 (12)	0.0345 (11)	0.0440 (11)	−0.0031 (9)	0.0015 (9)	0.0000 (9)
C12	0.0448 (13)	0.0326 (11)	0.0576 (13)	−0.0005 (9)	−0.0018 (10)	−0.0033 (10)
C13	0.0620 (15)	0.0300 (11)	0.0612 (15)	0.0031 (10)	−0.0007 (12)	0.0081 (10)
C14	0.0601 (14)	0.0359 (11)	0.0496 (13)	−0.0009 (10)	−0.0005 (11)	0.0109 (9)
C15	0.0370 (11)	0.0322 (10)	0.0441 (11)	−0.0042 (8)	−0.0016 (9)	0.0030 (8)
C16	0.0567 (13)	0.0268 (10)	0.0415 (11)	0.0019 (9)	0.0021 (10)	0.0002 (8)
C17	0.0626 (16)	0.0441 (13)	0.0495 (13)	0.0051 (11)	−0.0037 (11)	0.0025 (10)
C18	0.089 (2)	0.0514 (15)	0.0472 (14)	0.0086 (13)	−0.0120 (14)	0.0055 (11)
C19	0.112 (2)	0.0409 (13)	0.0391 (12)	−0.0041 (14)	0.0070 (14)	0.0062 (10)
C20	0.0813 (18)	0.0334 (11)	0.0529 (14)	−0.0071 (11)	0.0155 (13)	−0.0022 (10)
C21	0.0614 (14)	0.0315 (11)	0.0476 (12)	0.0009 (10)	0.0061 (10)	0.0026 (9)
C22	0.102 (2)	0.0675 (18)	0.082 (2)	−0.0143 (17)	0.0404 (18)	0.0048 (16)
C23	0.0752 (18)	0.0396 (13)	0.0686 (17)	0.0096 (12)	0.0006 (14)	−0.0068 (11)

Cl1—C1	1.737 (3)	C17—C18	1.376 (3)
N1—C7	1.324 (3)	C18—C19	1.365 (4)
N1—C15	1.358 (3)	C19—C20	1.380 (4)
C1—C2	1.355 (4)	C20—C21	1.388 (3)
C1—C6	1.375 (4)	C20—C22	1.501 (5)
C2—C3	1.379 (4)	C2—H2	0.9300
C3—C4	1.378 (3)	C3—H3	0.9300
C4—C5	1.375 (3)	C5—H5	0.9300
C4—C7	1.484 (3)	C6—H6	0.9300
C5—C6	1.368 (3)	C8—H8	0.9300
C7—C8	1.405 (3)	C11—H11	0.9300
C8—C9	1.355 (3)	C13—H13	0.9300
C9—C10	1.428 (3)	C14—H14	0.9300
C9—C16	1.486 (3)	C17—H17	0.9300
C10—C11	1.407 (3)	C18—H18	0.9300
C10—C15	1.406 (3)	C19—H19	0.9300
C11—C12	1.368 (3)	C21—H21	0.9300
C12—C13	1.401 (3)	C22—H22A	0.9600
C12—C23	1.502 (3)	C22—H22B	0.9600
C13—C14	1.355 (3)	C22—H22C	0.9600
C14—C15	1.417 (3)	C23—H23A	0.9600
C16—C17	1.384 (3)	C23—H23B	0.9600
C16—C21	1.381 (3)	C23—H23C	0.9600
C7—N1—C15	117.87 (17)	C21—C20—C22	120.5 (3)
Cl1—C1—C2	119.8 (2)	C16—C21—C20	121.8 (2)
Cl1—C1—C6	119.60 (19)	C1—C2—H2	120.00
C2—C1—C6	120.6 (2)	C3—C2—H2	120.00
C1—C2—C3	119.7 (2)	C2—C3—H3	119.00
C2—C3—C4	121.3 (2)	C4—C3—H3	119.00
C3—C4—C5	117.4 (2)	C4—C5—H5	119.00
C3—C4—C7	122.3 (2)	C6—C5—H5	119.00
C5—C4—C7	120.4 (2)	C1—C6—H6	121.00
C4—C5—C6	122.2 (2)	C5—C6—H6	121.00
C1—C6—C5	118.9 (2)	C7—C8—H8	119.00
N1—C7—C4	116.17 (18)	C9—C8—H8	119.00
N1—C7—C8	121.72 (18)	C10—C11—H11	119.00
C4—C7—C8	122.09 (18)	C12—C11—H11	119.00
C7—C8—C9	121.55 (19)	C12—C13—H13	119.00
C8—C9—C10	118.12 (18)	C14—C13—H13	119.00
C8—C9—C16	119.97 (18)	C13—C14—H14	120.00
C10—C9—C16	121.91 (18)	C15—C14—H14	120.00
C9—C10—C11	124.36 (19)	C16—C17—H17	120.00
C9—C10—C15	116.61 (17)	C18—C17—H17	120.00
C11—C10—C15	119.00 (18)	C17—C18—H18	120.00
C10—C11—C12	121.9 (2)	C19—C18—H18	120.00
C11—C12—C13	118.3 (2)	C18—C19—H19	119.00
C11—C12—C23	121.1 (2)	C20—C19—H19	119.00
C13—C12—C23	120.61 (19)	C16—C21—H21	119.00
C12—C13—C14	121.9 (2)	C20—C21—H21	119.00
C13—C14—C15	120.4 (2)	C20—C22—H22A	109.00
N1—C15—C10	124.08 (18)	C20—C22—H22B	109.00
N1—C15—C14	117.40 (18)	C20—C22—H22C	109.00
C10—C15—C14	118.52 (18)	H22A—C22—H22B	110.00
C9—C16—C17	120.3 (2)	H22A—C22—H22C	109.00
C9—C16—C21	121.1 (2)	H22B—C22—H22C	109.00
C17—C16—C21	118.6 (2)	C12—C23—H23A	109.00
C16—C17—C18	120.2 (2)	C12—C23—H23B	109.00
C17—C18—C19	120.3 (3)	C12—C23—H23C	109.00
C18—C19—C20	121.2 (2)	H23A—C23—H23B	109.00
C19—C20—C21	117.9 (3)	H23A—C23—H23C	110.00
C19—C20—C22	121.5 (2)	H23B—C23—H23C	110.00
C15—N1—C7—C8	−1.7 (3)	C8—C9—C10—C11	175.9 (2)
C7—N1—C15—C14	−178.93 (18)	C10—C9—C16—C21	−54.9 (3)
C7—N1—C15—C10	1.2 (3)	C10—C9—C16—C17	127.5 (2)
C15—N1—C7—C4	179.95 (17)	C15—C10—C11—C12	−1.7 (3)
Cl1—C1—C6—C5	−178.59 (19)	C9—C10—C15—N1	0.6 (3)
Cl1—C1—C2—C3	178.8 (2)	C11—C10—C15—N1	−177.30 (18)
C6—C1—C2—C3	−1.1 (4)	C11—C10—C15—C14	2.8 (3)
C2—C1—C6—C5	1.4 (4)	C9—C10—C15—C14	−179.27 (19)
C1—C2—C3—C4	−0.4 (5)	C9—C10—C11—C12	−179.4 (2)
C2—C3—C4—C7	−179.1 (2)	C10—C11—C12—C23	179.4 (2)
C2—C3—C4—C5	1.5 (4)	C10—C11—C12—C13	−0.4 (3)
C3—C4—C7—N1	176.7 (2)	C23—C12—C13—C14	−178.5 (2)
C5—C4—C7—C8	177.7 (2)	C11—C12—C13—C14	1.3 (4)
C5—C4—C7—N1	−3.9 (3)	C12—C13—C14—C15	−0.1 (4)
C3—C4—C5—C6	−1.3 (4)	C13—C14—C15—C10	−2.0 (3)
C7—C4—C5—C6	179.3 (2)	C13—C14—C15—N1	178.1 (2)
C3—C4—C7—C8	−1.6 (3)	C9—C16—C17—C18	178.9 (2)
C4—C5—C6—C1	−0.1 (4)	C21—C16—C17—C18	1.3 (3)
N1—C7—C8—C9	0.3 (3)	C9—C16—C21—C20	−178.7 (2)
C4—C7—C8—C9	178.6 (2)	C17—C16—C21—C20	−1.1 (3)
C7—C8—C9—C10	1.5 (3)	C16—C17—C18—C19	−0.1 (4)
C7—C8—C9—C16	−177.4 (2)	C17—C18—C19—C20	−1.5 (4)
C8—C9—C10—C15	−1.9 (3)	C18—C19—C20—C21	1.7 (4)
C16—C9—C10—C11	−5.3 (3)	C18—C19—C20—C22	−176.9 (2)
C8—C9—C16—C17	−53.6 (3)	C19—C20—C21—C16	−0.4 (3)
C8—C9—C16—C21	123.9 (2)	C22—C20—C21—C16	178.2 (2)
C16—C9—C10—C15	176.97 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N1	0.93	2.43	2.764 (3)	101