6-Methyl-2,4-diphenyl-quinoline.

The mol-ecules of the title compound, C(22)H(17)N, are linked by weak inter-actions, among which the most prominent are C-H⋯π inter-actions. The dihedral angles between the phenyl rings and the quinoline ring system are 43.3 (3) and 21.4 (3)°. The title product resulted from a three-component reaction of benzaldehyde, 1-ethynylbenzene and p-toluidine via C-H activation of 1-ethynylbenzene catalyzed by CuI in the ionic liquid 1-butyl-3-methyl-imidazolium hexa-fluoro-phosphate.

Related literature

For related literature, see: Allen et al. (1987 ▶); Park & Alper (2005 ▶); Shi et al. (2004 ▶); Skraup (1880 ▶).

Experimental

Crystal data

C22H17N

M = 295.37

Orthorhombic,

a = 7.766 (1) Å

b = 9.851 (1) Å

c = 20.756 (2) Å

V = 1588.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 294 (2) K

0.41 × 0.35 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.971, T max = 0.979

8562 measured reflections

1720 independent reflections

1302 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.120

S = 1.04

1720 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 1998 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808015651/fb2095sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015651/fb2095Isup2.hkl

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

C22H17N	F000 = 624
Mr = 295.37	Dx = 1.235 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P2ac2ab	Cell parameters from 803 reflections
a = 7.766 (1) Å	θ = 2.3–24.5º
b = 9.851 (1) Å	µ = 0.07 mm−1
c = 20.756 (2) Å	T = 294 (2) K
V = 1588.0 (3) Å3	Block, colourless
Z = 4	0.41 × 0.35 × 0.30 mm

Bruker SMART CCD area-detector diffractometer	1720 independent reflections
Radiation source: fine-focus sealed tube	1302 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.052
T = 294(2) K	θmax = 25.5º
ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −8→9
Tmin = 0.971, Tmax = 0.979	k = −11→11
8562 measured reflections	l = −25→22

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0684P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
1720 reflections	Δρmax = 0.17 e Å−3
210 parameters	Δρmin = −0.14 e Å−3
67 constraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.009 (2)

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
N1	0.8369 (3)	0.4866 (3)	0.14992 (11)	0.0493 (6)
C1	0.6966 (4)	0.5970 (3)	0.34443 (12)	0.0453 (7)
C2	0.7800 (4)	0.5422 (3)	0.39763 (13)	0.0538 (8)
H2	0.8605	0.4733	0.3920	0.065*
C3	0.7440 (5)	0.5893 (4)	0.45891 (14)	0.0640 (9)
H3	0.7997	0.5513	0.4942	0.077*
C4	0.6258 (5)	0.6926 (4)	0.46804 (14)	0.0678 (10)
H4	0.6016	0.7238	0.5093	0.081*
C5	0.5439 (5)	0.7489 (3)	0.41549 (13)	0.0621 (9)
H5	0.4649	0.8188	0.4214	0.074*
C6	0.5788 (4)	0.7021 (3)	0.35440 (13)	0.0493 (7)
H6	0.5232	0.7409	0.3193	0.059*
C7	0.8147 (4)	0.7190 (3)	0.11564 (12)	0.0448 (7)
C8	0.9118 (4)	0.6959 (3)	0.06060 (13)	0.0562 (8)
H8	0.9718	0.6147	0.0562	0.067*
C9	0.9206 (5)	0.7918 (3)	0.01228 (14)	0.0647 (9)
H9	0.9870	0.7750	−0.0242	0.078*
C10	0.8318 (5)	0.9124 (3)	0.01757 (15)	0.0638 (9)
H10	0.8375	0.9767	−0.0152	0.077*
C11	0.7347 (4)	0.9371 (3)	0.07175 (14)	0.0592 (9)
H11	0.6745	1.0182	0.0758	0.071*
C12	0.7268 (4)	0.8410 (3)	0.12009 (13)	0.0524 (8)
H12	0.6608	0.8586	0.1565	0.063*
C13	0.7370 (3)	0.5530 (3)	0.27752 (13)	0.0434 (7)
C14	0.7596 (3)	0.4139 (3)	0.25973 (13)	0.0448 (7)
C15	0.7277 (4)	0.3018 (3)	0.30025 (13)	0.0492 (7)
H15	0.6855	0.3175	0.3415	0.059*
C16	0.7564 (4)	0.1704 (3)	0.28110 (15)	0.0522 (8)
C17	0.8282 (4)	0.1481 (3)	0.22001 (14)	0.0559 (8)
H17	0.8570	0.0602	0.2077	0.067*
C18	0.8566 (4)	0.2523 (3)	0.17834 (14)	0.0545 (8)
H18	0.9014	0.2342	0.1377	0.065*
C19	0.8189 (4)	0.3880 (3)	0.19587 (13)	0.0454 (7)
C20	0.8015 (4)	0.6132 (3)	0.16636 (13)	0.0447 (7)
C21	0.7571 (4)	0.6497 (3)	0.23033 (12)	0.0472 (7)
H21	0.7413	0.7407	0.2406	0.057*
C22	0.7120 (5)	0.0522 (3)	0.32401 (16)	0.0677 (10)
H22A	0.6644	0.0853	0.3637	0.102*
H22B	0.8141	0.0007	0.3329	0.102*
H22C	0.6291	−0.0046	0.3028	0.102*

	U11	U22	U33	U12	U13	U23
N1	0.0537 (14)	0.0477 (15)	0.0465 (14)	0.0033 (13)	0.0026 (11)	−0.0044 (11)
C1	0.0542 (16)	0.0405 (15)	0.0412 (15)	−0.0047 (14)	−0.0011 (13)	−0.0024 (13)
C2	0.0665 (19)	0.0507 (18)	0.0444 (16)	−0.0062 (16)	−0.0071 (14)	−0.0017 (13)
C3	0.086 (2)	0.062 (2)	0.0436 (16)	−0.012 (2)	−0.0136 (16)	−0.0016 (16)
C4	0.094 (3)	0.068 (2)	0.0423 (17)	−0.014 (2)	0.0028 (17)	−0.0100 (16)
C5	0.076 (2)	0.0515 (19)	0.0586 (18)	−0.0029 (18)	0.0090 (17)	−0.0136 (17)
C6	0.0576 (17)	0.0474 (17)	0.0429 (15)	−0.0015 (16)	0.0037 (13)	−0.0029 (14)
C7	0.0497 (16)	0.0444 (17)	0.0404 (14)	0.0003 (14)	−0.0010 (13)	−0.0034 (13)
C8	0.0662 (19)	0.0513 (19)	0.0512 (17)	0.0081 (17)	0.0083 (15)	−0.0005 (15)
C9	0.084 (2)	0.064 (2)	0.0465 (17)	0.002 (2)	0.0151 (16)	0.0002 (17)
C10	0.092 (2)	0.052 (2)	0.0480 (18)	−0.004 (2)	−0.0054 (18)	0.0059 (16)
C11	0.075 (2)	0.0471 (18)	0.0557 (18)	0.0086 (18)	−0.0039 (16)	0.0001 (15)
C12	0.0601 (17)	0.0519 (18)	0.0451 (15)	0.0038 (16)	0.0013 (14)	−0.0036 (15)
C13	0.0448 (16)	0.0426 (16)	0.0428 (14)	−0.0009 (14)	−0.0007 (13)	−0.0007 (13)
C14	0.0447 (16)	0.0441 (16)	0.0455 (15)	0.0025 (14)	−0.0010 (12)	−0.0017 (13)
C15	0.0521 (17)	0.0498 (18)	0.0458 (15)	−0.0017 (15)	−0.0033 (13)	0.0019 (13)
C16	0.0533 (18)	0.0454 (18)	0.0579 (17)	0.0014 (15)	−0.0086 (15)	0.0009 (15)
C17	0.0617 (18)	0.0445 (18)	0.0616 (19)	0.0077 (16)	−0.0076 (16)	−0.0066 (16)
C18	0.0588 (18)	0.0524 (19)	0.0522 (18)	0.0091 (17)	0.0026 (14)	−0.0061 (17)
C19	0.0471 (15)	0.0438 (17)	0.0453 (15)	0.0023 (14)	0.0005 (13)	−0.0021 (13)
C20	0.0452 (15)	0.0453 (17)	0.0437 (15)	−0.0013 (14)	−0.0009 (12)	−0.0006 (13)
C21	0.0549 (17)	0.0417 (16)	0.0451 (15)	0.0032 (14)	0.0004 (14)	−0.0040 (14)
C22	0.079 (2)	0.0488 (19)	0.076 (2)	−0.0005 (18)	−0.0066 (19)	0.0077 (18)

N1—C20	1.322 (4)	C10—H10	0.9300
N1—C19	1.369 (3)	C11—C12	1.381 (4)
C1—C2	1.390 (4)	C11—H11	0.9300
C1—C6	1.396 (4)	C12—H12	0.9300
C1—C13	1.489 (4)	C13—C21	1.375 (4)
C2—C3	1.383 (4)	C13—C14	1.430 (4)
C2—H2	0.9300	C14—C15	1.410 (4)
C3—C4	1.384 (5)	C14—C19	1.426 (3)
C3—H3	0.9300	C15—C16	1.373 (4)
C4—C5	1.379 (4)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.403 (4)
C5—C6	1.376 (3)	C16—C22	1.506 (4)
C5—H5	0.9300	C17—C18	1.361 (4)
C6—H6	0.9300	C17—H17	0.9300
C7—C12	1.385 (4)	C18—C19	1.416 (4)
C7—C8	1.388 (4)	C18—H18	0.9300
C7—C20	1.485 (4)	C20—C21	1.418 (4)
C8—C9	1.380 (4)	C21—H21	0.9300
C8—H8	0.9300	C22—H22A	0.9600
C9—C10	1.378 (5)	C22—H22B	0.9600
C9—H9	0.9300	C22—H22C	0.9600
C10—C11	1.376 (4)
C20—N1—C19	118.0 (2)	C11—C12—H12	119.2
C2—C1—C6	118.4 (3)	C7—C12—H12	119.2
C2—C1—C13	122.0 (3)	C21—C13—C14	117.8 (2)
C6—C1—C13	119.5 (2)	C21—C13—C1	119.1 (3)
C3—C2—C1	120.4 (3)	C14—C13—C1	123.1 (2)
C3—C2—H2	119.8	C15—C14—C19	118.1 (3)
C1—C2—H2	119.8	C15—C14—C13	125.1 (2)
C2—C3—C4	120.5 (3)	C19—C14—C13	116.8 (3)
C2—C3—H3	119.8	C16—C15—C14	122.5 (3)
C4—C3—H3	119.8	C16—C15—H15	118.8
C5—C4—C3	119.6 (3)	C14—C15—H15	118.8
C5—C4—H4	120.2	C15—C16—C17	118.3 (3)
C3—C4—H4	120.2	C15—C16—C22	121.4 (3)
C6—C5—C4	120.2 (3)	C17—C16—C22	120.3 (3)
C6—C5—H5	119.9	C18—C17—C16	121.4 (3)
C4—C5—H5	119.9	C18—C17—H17	119.3
C5—C6—C1	120.9 (3)	C16—C17—H17	119.3
C5—C6—H6	119.5	C17—C18—C19	121.0 (3)
C1—C6—H6	119.5	C17—C18—H18	119.5
C12—C7—C8	117.7 (3)	C19—C18—H18	119.5
C12—C7—C20	121.8 (2)	N1—C19—C18	118.0 (2)
C8—C7—C20	120.4 (3)	N1—C19—C14	123.6 (3)
C9—C8—C7	120.9 (3)	C18—C19—C14	118.3 (3)
C9—C8—H8	119.6	N1—C20—C21	122.1 (3)
C7—C8—H8	119.6	N1—C20—C7	117.7 (2)
C10—C9—C8	120.5 (3)	C21—C20—C7	120.2 (3)
C10—C9—H9	119.7	C13—C21—C20	121.3 (3)
C8—C9—H9	119.7	C13—C21—H21	119.4
C11—C10—C9	119.4 (3)	C20—C21—H21	119.4
C11—C10—H10	120.3	C16—C22—H22A	109.5
C9—C10—H10	120.3	C16—C22—H22B	109.5
C10—C11—C12	119.8 (3)	H22A—C22—H22B	109.5
C10—C11—H11	120.1	C16—C22—H22C	109.5
C12—C11—H11	120.1	H22A—C22—H22C	109.5
C11—C12—C7	121.6 (3)	H22B—C22—H22C	109.5
C6—C1—C2—C3	1.2 (4)	C13—C14—C15—C16	−178.1 (3)
C13—C1—C2—C3	177.5 (3)	C14—C15—C16—C17	3.2 (4)
C1—C2—C3—C4	−0.6 (5)	C14—C15—C16—C22	−176.6 (3)
C2—C3—C4—C5	−0.2 (5)	C15—C16—C17—C18	−5.1 (5)
C3—C4—C5—C6	0.4 (5)	C22—C16—C17—C18	174.6 (3)
C4—C5—C6—C1	0.2 (5)	C16—C17—C18—C19	1.8 (5)
C2—C1—C6—C5	−1.0 (4)	C20—N1—C19—C18	179.9 (3)
C13—C1—C6—C5	−177.3 (3)	C20—N1—C19—C14	1.8 (4)
C12—C7—C8—C9	0.3 (4)	C17—C18—C19—N1	−174.7 (3)
C20—C7—C8—C9	178.0 (3)	C17—C18—C19—C14	3.5 (5)
C7—C8—C9—C10	−0.5 (5)	C15—C14—C19—N1	172.8 (3)
C8—C9—C10—C11	0.4 (5)	C13—C14—C19—N1	−7.1 (4)
C9—C10—C11—C12	−0.1 (5)	C15—C14—C19—C18	−5.3 (4)
C10—C11—C12—C7	0.0 (5)	C13—C14—C19—C18	174.8 (3)
C8—C7—C12—C11	−0.1 (4)	C19—N1—C20—C21	4.1 (4)
C20—C7—C12—C11	−177.7 (3)	C19—N1—C20—C7	−177.7 (2)
C2—C1—C13—C21	−135.1 (3)	C12—C7—C20—N1	157.1 (3)
C6—C1—C13—C21	41.1 (4)	C8—C7—C20—N1	−20.5 (4)
C2—C1—C13—C14	43.6 (4)	C12—C7—C20—C21	−24.7 (4)
C6—C1—C13—C14	−140.2 (3)	C8—C7—C20—C21	157.8 (3)
C21—C13—C14—C15	−173.5 (3)	C14—C13—C21—C20	−1.0 (4)
C1—C13—C14—C15	7.8 (4)	C1—C13—C21—C20	177.8 (2)
C21—C13—C14—C19	6.3 (4)	N1—C20—C21—C13	−4.6 (4)
C1—C13—C14—C19	−172.4 (3)	C7—C20—C21—C13	177.2 (3)
C19—C14—C15—C16	2.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg3i	0.93	2.75	3.551 (3)	145
C11—H11···Cg2i	0.93	2.92	3.726 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C1–C6 and C14–C19 rings, respectively .

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cg3i	0.93	2.75	3.551 (3)	145
C11—H11⋯Cg2i	0.93	2.92	3.726 (3)	146

Symmetry code: (i) .