2-(2-p-Tolyl-benzo[g]quinolin-3-yl)ethanol.

In the title compound, C(22)H(19)NO, the pyridine ring and the adjacent naphthalene ring system are nearly coplanar, making a dihedral angle of 3.3 (1)°, while the pyridine and benzene rings are perpendicular to each other, with a dihedral angle of 89.9 (1)°. The crystal packing is stabilized by inter-molecular O-H⋯N hydrogen bonds and C-H⋯π inter-actions.

Related literature

For the biological activity of quinoline derivatives, see: Faber et al. (1984 ▶); Johnson et al. (1989 ▶); Nesterova et al. (1995 ▶); Yamada et al. (1992 ▶).

Experimental

Crystal data

C22H19NO

M = 313.38

Triclinic,

a = 7.2044 (4) Å

b = 10.1704 (4) Å

c = 12.1194 (3) Å

α = 108.125 (3)°

β = 98.115 (4)°

γ = 99.370 (5)°

V = 815.08 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.49 × 0.21 × 0.07 mm

Data collection

Bruker APEXII area-detector diffractometer

10164 measured reflections

2879 independent reflections

2232 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.127

S = 1.03

2879 reflections

222 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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 datablock(s) global, I. DOI: 10.1107/S1600536811038736/hg5076sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038736/hg5076Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811038736/hg5076Isup3.cml

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

C22H19NO	Z = 2
Mr = 313.38	F(000) = 332
Triclinic, P1	Dx = 1.277 Mg m−3
Hall symbol: -P 1	Melting point = 486–487 K
a = 7.2044 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1704 (4) Å	Cell parameters from 3017 reflections
c = 12.1194 (3) Å	θ = 2.9–26.5°
α = 108.125 (3)°	µ = 0.08 mm−1
β = 98.115 (4)°	T = 296 K
γ = 99.370 (5)°	Sheet, yellow
V = 815.08 (6) Å3	0.49 × 0.21 × 0.07 mm

Bruker APEXII area-detector diffractometer	2232 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
graphite	θmax = 25.0°, θmin = 1.8°
phi and ω scans	h = −8→8
10164 measured reflections	k = −12→12
2879 independent reflections	l = −14→14

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0628P)2 + 0.1533P] where P = (Fo2 + 2Fc2)/3
2879 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.16 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
O1	0.94638 (19)	0.74485 (14)	0.16847 (12)	0.0671 (4)
N1	0.34813 (18)	0.89390 (13)	0.23730 (12)	0.0473 (3)
C4	0.5880 (2)	1.05942 (15)	0.19621 (13)	0.0428 (4)
C5	0.3959 (2)	0.99592 (15)	0.18921 (13)	0.0442 (4)
C1	0.4871 (2)	0.84951 (15)	0.29047 (13)	0.0445 (4)
C3	0.7299 (2)	1.00948 (15)	0.25305 (14)	0.0462 (4)
H3A	0.8585	1.0487	0.2594	0.055*
C13	0.6286 (2)	1.16905 (15)	0.14470 (13)	0.0442 (4)
C6	0.2436 (2)	1.03711 (17)	0.12868 (15)	0.0532 (4)
H6A	0.1167	0.9958	0.1250	0.064*
C2	0.6844 (2)	0.90436 (15)	0.29965 (13)	0.0452 (4)
C8	0.4736 (2)	1.20451 (15)	0.08298 (13)	0.0478 (4)
C16	0.4202 (2)	0.73826 (16)	0.34132 (14)	0.0454 (4)
C9	0.5119 (3)	1.30789 (17)	0.03012 (15)	0.0580 (5)
H9A	0.4103	1.3303	−0.0115	0.070*
C7	0.2812 (2)	1.13509 (17)	0.07688 (15)	0.0552 (4)
H7A	0.1795	1.1583	0.0360	0.066*
C19	0.2814 (2)	0.52892 (18)	0.43403 (17)	0.0545 (4)
C14	0.8416 (2)	0.84739 (17)	0.35334 (15)	0.0537 (4)
H14A	0.9579	0.9215	0.3842	0.064*
H14B	0.8043	0.8229	0.4195	0.064*
C18	0.3153 (2)	0.49386 (18)	0.32095 (16)	0.0594 (5)
H18A	0.2917	0.3987	0.2741	0.071*
C17	0.3831 (3)	0.59584 (17)	0.27504 (15)	0.0561 (4)
H17A	0.4043	0.5683	0.1980	0.067*
C12	0.8149 (2)	1.24194 (17)	0.15198 (16)	0.0557 (4)
H12A	0.9188	1.2210	0.1929	0.067*
C11	0.8479 (3)	1.34320 (18)	0.10038 (17)	0.0647 (5)
H11A	0.9730	1.3902	0.1066	0.078*
C15	0.8844 (2)	0.71879 (18)	0.26679 (17)	0.0583 (5)
H15A	0.9832	0.6864	0.3079	0.070*
H15B	0.7695	0.6433	0.2384	0.070*
C21	0.3886 (3)	0.77368 (18)	0.45560 (16)	0.0628 (5)
H21A	0.4142	0.8686	0.5032	0.075*
C22	0.2070 (3)	0.4166 (2)	0.4833 (2)	0.0769 (6)
H22A	0.2832	0.3461	0.4697	0.115*
H22B	0.0756	0.3728	0.4446	0.115*
H22C	0.2147	0.4591	0.5669	0.115*
C10	0.6947 (3)	1.37576 (18)	0.03868 (16)	0.0641 (5)
H10A	0.7174	1.4442	0.0032	0.077*
C20	0.3197 (3)	0.6706 (2)	0.50019 (17)	0.0655 (5)
H20A	0.2985	0.6978	0.5772	0.079*
H1	1.074 (4)	0.793 (3)	0.196 (2)	0.111 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0505 (8)	0.0835 (9)	0.0729 (9)	0.0124 (6)	0.0160 (6)	0.0342 (7)
N1	0.0446 (7)	0.0461 (7)	0.0529 (8)	0.0092 (6)	0.0146 (6)	0.0176 (6)
C4	0.0459 (9)	0.0390 (7)	0.0424 (8)	0.0093 (6)	0.0116 (7)	0.0115 (6)
C5	0.0462 (9)	0.0418 (8)	0.0442 (9)	0.0108 (6)	0.0123 (7)	0.0122 (7)
C1	0.0457 (9)	0.0433 (8)	0.0445 (9)	0.0090 (7)	0.0133 (7)	0.0138 (7)
C3	0.0420 (8)	0.0455 (8)	0.0515 (9)	0.0058 (6)	0.0109 (7)	0.0185 (7)
C13	0.0518 (9)	0.0387 (8)	0.0414 (9)	0.0114 (7)	0.0109 (7)	0.0112 (6)
C6	0.0435 (9)	0.0544 (9)	0.0620 (11)	0.0125 (7)	0.0105 (8)	0.0196 (8)
C2	0.0467 (9)	0.0437 (8)	0.0458 (9)	0.0087 (7)	0.0107 (7)	0.0161 (7)
C8	0.0593 (10)	0.0411 (8)	0.0414 (9)	0.0149 (7)	0.0098 (7)	0.0101 (7)
C16	0.0404 (8)	0.0477 (8)	0.0503 (9)	0.0072 (6)	0.0123 (7)	0.0199 (7)
C9	0.0745 (12)	0.0502 (9)	0.0514 (10)	0.0205 (9)	0.0074 (9)	0.0196 (8)
C7	0.0532 (10)	0.0549 (9)	0.0581 (10)	0.0199 (8)	0.0059 (8)	0.0184 (8)
C19	0.0383 (8)	0.0633 (10)	0.0714 (12)	0.0083 (7)	0.0124 (8)	0.0373 (9)
C14	0.0480 (9)	0.0580 (10)	0.0600 (11)	0.0053 (7)	0.0062 (8)	0.0322 (8)
C18	0.0601 (11)	0.0470 (9)	0.0667 (12)	0.0011 (8)	0.0105 (9)	0.0200 (8)
C17	0.0647 (11)	0.0514 (9)	0.0492 (10)	0.0049 (8)	0.0133 (8)	0.0162 (8)
C12	0.0542 (10)	0.0522 (9)	0.0649 (11)	0.0081 (7)	0.0108 (8)	0.0283 (8)
C11	0.0668 (12)	0.0573 (10)	0.0725 (12)	0.0023 (9)	0.0126 (10)	0.0322 (9)
C15	0.0444 (9)	0.0620 (10)	0.0790 (12)	0.0120 (8)	0.0151 (9)	0.0373 (9)
C21	0.0784 (12)	0.0499 (9)	0.0585 (11)	0.0069 (8)	0.0286 (9)	0.0136 (8)
C22	0.0576 (11)	0.0869 (14)	0.1071 (17)	0.0101 (10)	0.0221 (11)	0.0628 (13)
C10	0.0861 (14)	0.0502 (9)	0.0610 (11)	0.0119 (9)	0.0129 (10)	0.0284 (9)
C20	0.0731 (12)	0.0716 (12)	0.0567 (11)	0.0087 (9)	0.0272 (9)	0.0264 (9)

O1—C15	1.413 (2)	C7—H7A	0.9300
O1—H1	0.93 (3)	C19—C18	1.372 (3)
N1—C1	1.3294 (19)	C19—C20	1.373 (3)
N1—C5	1.3606 (19)	C19—C22	1.505 (2)
C4—C3	1.402 (2)	C14—C15	1.508 (2)
C4—C5	1.407 (2)	C14—H14A	0.9700
C4—C13	1.448 (2)	C14—H14B	0.9700
C5—C6	1.426 (2)	C18—C17	1.377 (2)
C1—C2	1.415 (2)	C18—H18A	0.9300
C1—C16	1.494 (2)	C17—H17A	0.9300
C3—C2	1.372 (2)	C12—C11	1.368 (2)
C3—H3A	0.9300	C12—H12A	0.9300
C13—C12	1.400 (2)	C11—C10	1.388 (3)
C13—C8	1.414 (2)	C11—H11A	0.9300
C6—C7	1.345 (2)	C15—H15A	0.9700
C6—H6A	0.9300	C15—H15B	0.9700
C2—C14	1.511 (2)	C21—C20	1.377 (2)
C8—C9	1.402 (2)	C21—H21A	0.9300
C8—C7	1.430 (2)	C22—H22A	0.9600
C16—C17	1.380 (2)	C22—H22B	0.9600
C16—C21	1.380 (2)	C22—H22C	0.9600
C9—C10	1.357 (3)	C10—H10A	0.9300
C9—H9A	0.9300	C20—H20A	0.9300
C15—O1—H1	105.8 (15)	C15—C14—H14A	108.9
C1—N1—C5	119.18 (13)	C2—C14—H14A	108.9
C3—C4—C5	116.48 (14)	C15—C14—H14B	108.9
C3—C4—C13	123.98 (14)	C2—C14—H14B	108.9
C5—C4—C13	119.54 (14)	H14A—C14—H14B	107.7
N1—C5—C4	122.42 (14)	C19—C18—C17	121.72 (16)
N1—C5—C6	117.78 (14)	C19—C18—H18A	119.1
C4—C5—C6	119.79 (14)	C17—C18—H18A	119.1
N1—C1—C2	122.65 (14)	C18—C17—C16	121.16 (16)
N1—C1—C16	115.17 (13)	C18—C17—H17A	119.4
C2—C1—C16	122.17 (14)	C16—C17—H17A	119.4
C2—C3—C4	121.90 (14)	C11—C12—C13	121.65 (17)
C2—C3—H3A	119.1	C11—C12—H12A	119.2
C4—C3—H3A	119.0	C13—C12—H12A	119.2
C12—C13—C8	117.79 (14)	C12—C11—C10	120.04 (18)
C12—C13—C4	123.31 (14)	C12—C11—H11A	120.0
C8—C13—C4	118.90 (14)	C10—C11—H11A	120.0
C7—C6—C5	120.72 (15)	O1—C15—C14	113.27 (14)
C7—C6—H6A	119.6	O1—C15—H15A	108.9
C5—C6—H6A	119.6	C14—C15—H15A	108.9
C3—C2—C1	117.33 (14)	O1—C15—H15B	108.9
C3—C2—C14	120.10 (14)	C14—C15—H15B	108.9
C1—C2—C14	122.52 (13)	H15A—C15—H15B	107.7
C9—C8—C13	119.27 (15)	C20—C21—C16	121.03 (16)
C9—C8—C7	121.50 (15)	C20—C21—H21A	119.5
C13—C8—C7	119.23 (14)	C16—C21—H21A	119.5
C17—C16—C21	117.21 (15)	C19—C22—H22A	109.5
C17—C16—C1	121.38 (14)	C19—C22—H22B	109.5
C21—C16—C1	121.40 (14)	H22A—C22—H22B	109.5
C10—C9—C8	121.18 (16)	C19—C22—H22C	109.5
C10—C9—H9A	119.4	H22A—C22—H22C	109.5
C8—C9—H9A	119.4	H22B—C22—H22C	109.5
C6—C7—C8	121.74 (15)	C9—C10—C11	120.07 (16)
C6—C7—H7A	119.1	C9—C10—H10A	120.0
C8—C7—H7A	119.1	C11—C10—H10A	120.0
C18—C19—C20	117.08 (15)	C19—C20—C21	121.80 (17)
C18—C19—C22	121.27 (17)	C19—C20—H20A	119.1
C20—C19—C22	121.65 (17)	C21—C20—H20A	119.1
C15—C14—C2	113.54 (14)
C1—N1—C5—C4	−1.7 (2)	C2—C1—C16—C17	−90.9 (2)
C1—N1—C5—C6	177.53 (13)	N1—C1—C16—C21	−88.66 (19)
C3—C4—C5—N1	1.6 (2)	C2—C1—C16—C21	90.7 (2)
C13—C4—C5—N1	−179.01 (13)	C13—C8—C9—C10	−1.0 (2)
C3—C4—C5—C6	−177.56 (13)	C7—C8—C9—C10	178.41 (15)
C13—C4—C5—C6	1.8 (2)	C5—C6—C7—C8	−1.8 (3)
C5—N1—C1—C2	0.2 (2)	C9—C8—C7—C6	−179.16 (15)
C5—N1—C1—C16	179.51 (12)	C13—C8—C7—C6	0.2 (2)
C5—C4—C3—C2	−0.1 (2)	C3—C2—C14—C15	−92.86 (18)
C13—C4—C3—C2	−179.40 (13)	C1—C2—C14—C15	84.48 (19)
C3—C4—C13—C12	−3.5 (2)	C20—C19—C18—C17	−0.5 (3)
C5—C4—C13—C12	177.21 (14)	C22—C19—C18—C17	179.92 (16)
C3—C4—C13—C8	176.03 (13)	C19—C18—C17—C16	0.1 (3)
C5—C4—C13—C8	−3.3 (2)	C21—C16—C17—C18	0.7 (3)
N1—C5—C6—C7	−178.50 (14)	C1—C16—C17—C18	−177.77 (15)
C4—C5—C6—C7	0.7 (2)	C8—C13—C12—C11	−0.7 (2)
C4—C3—C2—C1	−1.3 (2)	C4—C13—C12—C11	178.83 (15)
C4—C3—C2—C14	176.17 (14)	C13—C12—C11—C10	−0.1 (3)
N1—C1—C2—C3	1.3 (2)	C2—C14—C15—O1	60.50 (18)
C16—C1—C2—C3	−177.99 (13)	C17—C16—C21—C20	−1.1 (3)
N1—C1—C2—C14	−176.11 (14)	C1—C16—C21—C20	177.39 (17)
C16—C1—C2—C14	4.6 (2)	C8—C9—C10—C11	0.1 (3)
C12—C13—C8—C9	1.2 (2)	C12—C11—C10—C9	0.4 (3)
C4—C13—C8—C9	−178.32 (13)	C18—C19—C20—C21	0.1 (3)
C12—C13—C8—C7	−178.16 (14)	C22—C19—C20—C21	179.70 (17)
C4—C13—C8—C7	2.3 (2)	C16—C21—C20—C19	0.7 (3)
N1—C1—C16—C17	89.77 (18)

Cg is the centroid of the N1,C1–C5 pyridine ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.93 (3)	1.98 (3)	2.9110 (18)	174 (2)
C21—H21A···Cgii	0.93	2.97	3.7358 (19)	140.

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N1,C1–C5 pyridine ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.93 (3)	1.98 (3)	2.9110 (18)	174 (2)
C21—H21A⋯Cgii	0.93	2.97	3.7358 (19)	140

Symmetry codes: (i) ; (ii) .