4-[2-(Benzyl-amino)-phen-yl]-2,6-dimethyl-quinoline N-oxide.

The title compound, C(24)H(22)N(2)O, was obtained in a two-step procedure from the corresponding 4-(2-iodo-phen-yl)quinoline. The quinoline system is approximately planar [maximum deviation from the least-squares plane = 0.021 (2) Å]. The planes of the quinoline system and the phenyl ring subtend a dihedral angle of 78.08 (8)°. In the crystal, pairs of mol-ecules are connected via a center of symmetry and linked by a pair of angular N-H⋯O hydrogen bond. These dimers form columns oriented along the c axis.

Related literature

For aminations of iodo­lium salts, see: Letessier et al. (2011 ▶), Letessier & Detert (2012 ▶). For quinoline N-oxides, see: Moreno-Fuquen et al. (2007 ▶); Ivashevskaja et al. (2002 ▶); Fahl­quist et al. (2006 ▶). For heteroanalogous carbazoles, see: Dassonneville et al. (2010 ▶, 2011 ▶); Nissen & Detert (2011 ▶). For Buchwald-Hartwig amination, see: Hartwig (1999 ▶); Muci & Buchwald (2002 ▶). For twist of o-substituted biaryls, see: Miao et al. (2009 ▶); Moschel et al. (2011 ▶).

Experimental

Crystal data

C24H22N2O

M = 354.44

Monoclinic,

a = 10.1656 (3) Å

b = 14.1135 (5) Å

c = 12.9372 (4) Å

β = 91.547 (3)°

V = 1855.46 (11) Å3

Z = 4

Cu Kα radiation

μ = 0.61 mm−1

T = 193 K

0.26 × 0.18 × 0.18 mm

Data collection

Stoe IPDS 2T diffractometer

18005 measured reflections

3120 independent reflections

2803 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.154

S = 1.10

3120 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Data collection: X-AREA (Stoe & Cie, 2011) ▶; cell refinement: X-AREA ▶; data reduction: X-RED (Stoe & Cie, 2011) ▶; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812011002/bt5844sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011002/bt5844Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011002/bt5844Isup3.cml

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

C24H22N2O	F(000) = 752
Mr = 354.44	Dx = 1.269 Mg m−3
Monoclinic, P21/n	Melting point: 449 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54178 Å
a = 10.1656 (3) Å	Cell parameters from 27155 reflections
b = 14.1135 (5) Å	θ = 3.1–68.2°
c = 12.9372 (4) Å	µ = 0.61 mm−1
β = 91.547 (3)°	T = 193 K
V = 1855.46 (11) Å3	Needle, yellow
Z = 4	0.26 × 0.18 × 0.18 mm

Stoe IPDS 2T diffractometer	2803 reflections with I > 2σ(I)
Radiation source: Incoatec microSource Cu	Rint = 0.034
X-ray mirror monochromator	θmax = 66.5°, θmin = 4.6°
Detector resolution: 6.67 pixels mm-1	h = −12→12
rotation method scans	k = −16→16
18005 measured reflections	l = −13→13
3120 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.099P)2 + 0.2406P] where P = (Fo2 + 2Fc2)/3
3120 reflections	(Δ/σ)max < 0.001
246 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Experimental. 1H-NMR (400 MHz, CDCl3): δ = 8.71 (d, 3J = 8.9 Hz, 1 H), 7.59 (dd, 3J = 8.9 Hz, 4 J = 1.7 Hz, 1 H), 7.43 (s, 1 H), 7.36 - 7.16 (m, 7 H), 7.11 (dd, 3 J = 7.4 Hz, 4J = 1.5 Hz, 1 H), 6.84 (t, 3J = 7.4 Hz, 1 H), 6.75 (d, 3J = 8.2 Hz, 1 H), 4.30 (s, 2 H, CH2), 2.71 (s, 3 H, CH3), 2.47 (s, 3 H, CH3).13C-NMR (75 MHz, CDCl3): δ = 145.6, 144.0, 140.4, 139.7, 137.0, 133.4, 131.8, 130.3, 129.4, 128.3 (2 C), 128.0, 126.7 (2 C), 126.5, 125.5, 125.1, 121.8, 119.4, 115.7, 110.4, 45.9, 21.0, 18.2.IR (ATR) ν = 3324, 3016, 2910, 2857, 1597, 1573, 1520, 1410, 1385, 1319, 1300, 1237, 1201, 1162, 1105, 982, 925, 872, 823, 795, 738, 699 cm-1.ESI-MS: 355.2 (M+H)+

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
C1	0.71651 (14)	0.61537 (10)	0.20685 (11)	0.0467 (4)
C2	0.77995 (15)	0.65594 (11)	0.12222 (12)	0.0519 (4)
H2	0.7410	0.7089	0.0880	0.062*
C3	0.89744 (16)	0.62050 (12)	0.08793 (13)	0.0561 (4)
H3	0.9384	0.6496	0.0309	0.067*
C4	0.95605 (15)	0.54320 (12)	0.13561 (13)	0.0570 (4)
H4	1.0372	0.5190	0.1122	0.068*
C5	0.89426 (14)	0.50159 (11)	0.21827 (13)	0.0520 (4)
H5	0.9344	0.4485	0.2513	0.062*
C6	0.77536 (14)	0.53505 (10)	0.25443 (11)	0.0461 (4)
N7	0.60350 (13)	0.65335 (9)	0.24471 (10)	0.0533 (4)
H7	0.5685	0.6237	0.3051	0.064*
C8	0.53902 (15)	0.73596 (11)	0.20054 (12)	0.0533 (4)
H8A	0.6068	0.7844	0.1866	0.064*
H8B	0.4795	0.7627	0.2524	0.064*
C9	0.46014 (14)	0.71777 (10)	0.10157 (12)	0.0507 (4)
C10	0.46398 (16)	0.78089 (11)	0.01988 (13)	0.0572 (4)
H10	0.5201	0.8346	0.0249	0.069*
C11	0.38731 (18)	0.76708 (12)	−0.06926 (14)	0.0637 (5)
H11	0.3914	0.8110	−0.1247	0.076*
C12	0.30522 (17)	0.68959 (13)	−0.07725 (15)	0.0640 (5)
H12	0.2516	0.6805	−0.1377	0.077*
C13	0.30119 (17)	0.62530 (13)	0.00294 (16)	0.0660 (5)
H13	0.2456	0.5713	−0.0028	0.079*
C14	0.37786 (16)	0.63914 (12)	0.09166 (14)	0.0608 (4)
H14	0.3744	0.5945	0.1465	0.073*
C15	0.71631 (14)	0.48715 (10)	0.34537 (12)	0.0474 (4)
C15A	0.59375 (14)	0.43752 (10)	0.33858 (12)	0.0491 (4)
C16	0.51672 (14)	0.43056 (10)	0.24628 (13)	0.0520 (4)
H16	0.5461	0.4613	0.1858	0.062*
C17	0.40017 (15)	0.38053 (11)	0.24148 (15)	0.0596 (4)
C18	0.35773 (17)	0.33600 (13)	0.33235 (18)	0.0695 (5)
H18	0.2770	0.3020	0.3302	0.083*
C19	0.42868 (17)	0.34010 (12)	0.42324 (17)	0.0670 (5)
H19	0.3978	0.3092	0.4832	0.080*
C19A	0.54775 (15)	0.39039 (11)	0.42727 (13)	0.0549 (4)
N20	0.62225 (14)	0.39157 (10)	0.51958 (11)	0.0584 (4)
C21	0.73692 (17)	0.43875 (11)	0.52665 (13)	0.0567 (4)
C22	0.78247 (16)	0.48609 (11)	0.43914 (12)	0.0529 (4)
H22	0.8636	0.5192	0.4452	0.063*
C23	0.31976 (18)	0.37395 (14)	0.14289 (18)	0.0732 (5)
H23A	0.2438	0.4165	0.1465	0.110*
H23B	0.2890	0.3087	0.1330	0.110*
H23C	0.3739	0.3924	0.0846	0.110*
O24	0.57999 (13)	0.34483 (10)	0.59927 (10)	0.0755 (4)
C25	0.8079 (2)	0.43775 (15)	0.62843 (14)	0.0725 (5)
H25A	0.8872	0.4770	0.6248	0.109*
H25B	0.8328	0.3726	0.6462	0.109*
H25C	0.7505	0.4631	0.6815	0.109*

	U11	U22	U33	U12	U13	U23
C1	0.0483 (8)	0.0467 (8)	0.0453 (8)	−0.0049 (6)	0.0027 (6)	−0.0022 (6)
C2	0.0552 (8)	0.0504 (8)	0.0504 (9)	−0.0038 (6)	0.0054 (6)	0.0039 (6)
C3	0.0553 (9)	0.0606 (9)	0.0529 (9)	−0.0096 (7)	0.0093 (7)	0.0038 (7)
C4	0.0469 (8)	0.0643 (10)	0.0603 (10)	−0.0025 (7)	0.0106 (7)	0.0007 (7)
C5	0.0482 (8)	0.0514 (8)	0.0565 (9)	−0.0014 (6)	0.0029 (7)	0.0016 (6)
C6	0.0469 (7)	0.0450 (7)	0.0464 (8)	−0.0060 (6)	0.0025 (6)	−0.0020 (6)
N7	0.0584 (8)	0.0509 (7)	0.0513 (8)	0.0061 (5)	0.0123 (6)	0.0076 (5)
C8	0.0588 (9)	0.0458 (8)	0.0557 (9)	0.0033 (6)	0.0101 (7)	0.0010 (6)
C9	0.0492 (8)	0.0465 (8)	0.0569 (9)	0.0076 (6)	0.0108 (6)	0.0007 (6)
C10	0.0603 (9)	0.0472 (8)	0.0641 (10)	0.0020 (7)	0.0032 (7)	0.0051 (7)
C11	0.0701 (10)	0.0568 (9)	0.0638 (11)	0.0095 (8)	−0.0024 (8)	0.0065 (8)
C12	0.0578 (9)	0.0650 (10)	0.0688 (11)	0.0128 (8)	−0.0036 (8)	−0.0081 (8)
C13	0.0590 (10)	0.0599 (10)	0.0792 (12)	−0.0035 (7)	0.0018 (8)	−0.0045 (8)
C14	0.0603 (9)	0.0541 (9)	0.0683 (11)	−0.0014 (7)	0.0103 (8)	0.0060 (8)
C15	0.0491 (8)	0.0420 (7)	0.0513 (9)	0.0026 (6)	0.0068 (6)	0.0002 (6)
C15A	0.0494 (8)	0.0400 (7)	0.0584 (9)	0.0041 (6)	0.0122 (6)	0.0014 (6)
C16	0.0507 (8)	0.0435 (8)	0.0621 (10)	0.0006 (6)	0.0084 (7)	−0.0015 (6)
C17	0.0486 (8)	0.0467 (8)	0.0838 (12)	0.0007 (6)	0.0078 (8)	−0.0028 (7)
C18	0.0492 (9)	0.0546 (9)	0.1052 (16)	−0.0036 (7)	0.0162 (9)	0.0077 (9)
C19	0.0559 (9)	0.0568 (10)	0.0895 (13)	0.0044 (7)	0.0254 (9)	0.0170 (8)
C19A	0.0535 (8)	0.0469 (8)	0.0651 (11)	0.0093 (6)	0.0174 (7)	0.0074 (7)
N20	0.0649 (8)	0.0536 (8)	0.0578 (9)	0.0140 (6)	0.0227 (6)	0.0111 (6)
C21	0.0651 (9)	0.0525 (8)	0.0530 (10)	0.0118 (7)	0.0120 (7)	0.0027 (7)
C22	0.0574 (8)	0.0491 (8)	0.0523 (9)	0.0026 (6)	0.0052 (7)	0.0007 (6)
C23	0.0560 (10)	0.0622 (10)	0.1011 (15)	−0.0063 (8)	−0.0062 (9)	−0.0083 (9)
O24	0.0814 (8)	0.0774 (9)	0.0694 (9)	0.0177 (6)	0.0337 (7)	0.0280 (6)
C25	0.0907 (13)	0.0757 (12)	0.0512 (10)	0.0172 (10)	0.0075 (9)	0.0057 (8)

C1—N7	1.370 (2)	C13—H13	0.9500
C1—C2	1.407 (2)	C14—H14	0.9500
C1—C6	1.415 (2)	C15—C22	1.371 (2)
C2—C3	1.379 (2)	C15—C15A	1.430 (2)
C2—H2	0.9500	C15A—C16	1.414 (2)
C3—C4	1.381 (2)	C15A—C19A	1.417 (2)
C3—H3	0.9500	C16—C17	1.379 (2)
C4—C5	1.385 (2)	C16—H16	0.9500
C4—H4	0.9500	C17—C18	1.411 (3)
C5—C6	1.390 (2)	C17—C23	1.499 (3)
C5—H5	0.9500	C18—C19	1.364 (3)
C6—C15	1.497 (2)	C18—H18	0.9500
N7—C8	1.448 (2)	C19—C19A	1.403 (2)
N7—H7	0.9629	C19—H19	0.9500
C8—C9	1.514 (2)	C19A—N20	1.397 (2)
C8—H8A	0.9900	N20—O24	1.3064 (17)
C8—H8B	0.9900	N20—C21	1.343 (2)
C9—C10	1.384 (2)	C21—C22	1.404 (2)
C9—C14	1.393 (2)	C21—C25	1.484 (3)
C10—C11	1.388 (2)	C22—H22	0.9500
C10—H10	0.9500	C23—H23A	0.9800
C11—C12	1.378 (3)	C23—H23B	0.9800
C11—H11	0.9500	C23—H23C	0.9800
C12—C13	1.380 (3)	C25—H25A	0.9800
C12—H12	0.9500	C25—H25B	0.9800
C13—C14	1.384 (3)	C25—H25C	0.9800
N7—C1—C2	121.68 (14)	C9—C14—H14	119.6
N7—C1—C6	120.44 (13)	C22—C15—C15A	117.05 (14)
C2—C1—C6	117.85 (13)	C22—C15—C6	120.19 (13)
C3—C2—C1	121.45 (15)	C15A—C15—C6	122.70 (14)
C3—C2—H2	119.3	C16—C15A—C19A	117.66 (14)
C1—C2—H2	119.3	C16—C15A—C15	123.22 (14)
C2—C3—C4	120.66 (15)	C19A—C15A—C15	119.10 (15)
C2—C3—H3	119.7	C17—C16—C15A	121.95 (15)
C4—C3—H3	119.7	C17—C16—H16	119.0
C3—C4—C5	118.73 (15)	C15A—C16—H16	119.0
C3—C4—H4	120.6	C16—C17—C18	118.18 (17)
C5—C4—H4	120.6	C16—C17—C23	121.20 (16)
C4—C5—C6	122.15 (15)	C18—C17—C23	120.62 (15)
C4—C5—H5	118.9	C19—C18—C17	122.21 (16)
C6—C5—H5	118.9	C19—C18—H18	118.9
C5—C6—C1	119.14 (13)	C17—C18—H18	118.9
C5—C6—C15	118.80 (13)	C18—C19—C19A	119.28 (17)
C1—C6—C15	122.01 (13)	C18—C19—H19	120.4
C1—N7—C8	123.31 (13)	C19A—C19—H19	120.4
C1—N7—H7	116.8	N20—C19A—C19	119.02 (15)
C8—N7—H7	119.8	N20—C19A—C15A	120.24 (14)
N7—C8—C9	114.90 (13)	C19—C19A—C15A	120.72 (17)
N7—C8—H8A	108.5	O24—N20—C21	119.97 (15)
C9—C8—H8A	108.5	O24—N20—C19A	119.11 (14)
N7—C8—H8B	108.5	C21—N20—C19A	120.91 (13)
C9—C8—H8B	108.5	N20—C21—C22	119.03 (15)
H8A—C8—H8B	107.5	N20—C21—C25	117.11 (15)
C10—C9—C14	118.15 (15)	C22—C21—C25	123.85 (16)
C10—C9—C8	120.76 (14)	C15—C22—C21	123.65 (15)
C14—C9—C8	121.04 (14)	C15—C22—H22	118.2
C9—C10—C11	121.16 (16)	C21—C22—H22	118.2
C9—C10—H10	119.4	C17—C23—H23A	109.5
C11—C10—H10	119.4	C17—C23—H23B	109.5
C12—C11—C10	119.94 (16)	H23A—C23—H23B	109.5
C12—C11—H11	120.0	C17—C23—H23C	109.5
C10—C11—H11	120.0	H23A—C23—H23C	109.5
C11—C12—C13	119.73 (16)	H23B—C23—H23C	109.5
C11—C12—H12	120.1	C21—C25—H25A	109.5
C13—C12—H12	120.1	C21—C25—H25B	109.5
C12—C13—C14	120.23 (16)	H25A—C25—H25B	109.5
C12—C13—H13	119.9	C21—C25—H25C	109.5
C14—C13—H13	119.9	H25A—C25—H25C	109.5
C13—C14—C9	120.79 (16)	H25B—C25—H25C	109.5
C13—C14—H14	119.6
N7—C1—C2—C3	176.45 (14)	C6—C15—C15A—C16	−1.0 (2)
C6—C1—C2—C3	−1.6 (2)	C22—C15—C15A—C19A	−0.2 (2)
C1—C2—C3—C4	0.5 (2)	C6—C15—C15A—C19A	177.09 (13)
C2—C3—C4—C5	0.3 (2)	C19A—C15A—C16—C17	0.5 (2)
C3—C4—C5—C6	0.1 (2)	C15—C15A—C16—C17	178.62 (14)
C4—C5—C6—C1	−1.3 (2)	C15A—C16—C17—C18	0.4 (2)
C4—C5—C6—C15	−178.91 (14)	C15A—C16—C17—C23	179.98 (14)
N7—C1—C6—C5	−176.09 (14)	C16—C17—C18—C19	−0.8 (3)
C2—C1—C6—C5	2.0 (2)	C23—C17—C18—C19	179.66 (16)
N7—C1—C6—C15	1.4 (2)	C17—C18—C19—C19A	0.2 (3)
C2—C1—C6—C15	179.53 (13)	C18—C19—C19A—N20	−177.79 (14)
C2—C1—N7—C8	1.3 (2)	C18—C19—C19A—C15A	0.7 (2)
C6—C1—N7—C8	179.29 (13)	C16—C15A—C19A—N20	177.44 (12)
C1—N7—C8—C9	77.05 (18)	C15—C15A—C19A—N20	−0.8 (2)
N7—C8—C9—C10	−138.41 (15)	C16—C15A—C19A—C19	−1.1 (2)
N7—C8—C9—C14	44.11 (19)	C15—C15A—C19A—C19	−179.29 (14)
C14—C9—C10—C11	0.6 (2)	C19—C19A—N20—O24	0.9 (2)
C8—C9—C10—C11	−176.96 (14)	C15A—C19A—N20—O24	−177.63 (13)
C9—C10—C11—C12	0.2 (2)	C19—C19A—N20—C21	179.90 (15)
C10—C11—C12—C13	−1.0 (3)	C15A—C19A—N20—C21	1.4 (2)
C11—C12—C13—C14	0.9 (3)	O24—N20—C21—C22	178.06 (13)
C12—C13—C14—C9	−0.0 (3)	C19A—N20—C21—C22	−0.9 (2)
C10—C9—C14—C13	−0.7 (2)	O24—N20—C21—C25	−2.3 (2)
C8—C9—C14—C13	176.86 (15)	C19A—N20—C21—C25	178.73 (13)
C5—C6—C15—C22	61.76 (19)	C15A—C15—C22—C21	0.6 (2)
C1—C6—C15—C22	−115.76 (16)	C6—C15—C22—C21	−176.72 (14)
C5—C6—C15—C15A	−115.43 (16)	N20—C21—C22—C15	−0.1 (2)
C1—C6—C15—C15A	67.05 (19)	C25—C21—C22—C15	−179.72 (15)
C22—C15—C15A—C16	−178.31 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O24i	0.96	2.03	2.7852 (17)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯O24i	0.96	2.03	2.7852 (17)	134

Symmetry code: (i) .