2-p-Tolyl-2,3-di-hydro-quinolin-4(1H)-one.

In the title mol-ecule, C16H15NO, the tetra-hydro-pyridine ring is in a sofa conformation with the methine C atom forming the flap. The dihedral angle between the benzene rings is 80.85 (8)°. In the crystal, mol-ecules are arranged in alternating double layers parallel to (100) and are connected along [001] by N-H⋯O hydrogen bonds. In addition, weak C-H⋯π inter-actions are observed.

Related literature

For applications of quinolines, see: Hepworth (1984 ▶). For the synthesis and applications of similar compounds see: Donnelly & Farrell (1990a ▶,b ▶); Chandrasekhar et al. (2007 ▶); Kumar et al. (2004 ▶); Gordon (2001 ▶); Olivier-Bourbigou & Magna (2002 ▶); Tokes & Szilagyi (1987 ▶); Tokes & Litkei (1993 ▶); Benzerka et al. (2012 ▶, 2013 ▶); Hayour et al. (2011 ▶) Chelghoum et al. (2012 ▶). For related structures, see: Tokes et al. (1992 ▶); Benzerka et al. (2011 ▶); Bouraiou et al. (2011 ▶).

Experimental

Crystal data

C16H15NO

M = 237.29

Monoclinic,

a = 17.6363 (14) Å

b = 10.7968 (9) Å

c = 13.6308 (9) Å

β = 103.260 (3)°

V = 2526.3 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 150 K

0.52 × 0.33 × 0.27 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.873, T max = 0.979

6746 measured reflections

2875 independent reflections

2279 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.153

S = 1.05

2875 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.69 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and CRYSCAL (T. Roisnel, local program).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814001676/lh5684sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001676/lh5684Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001676/lh5684Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H15NO	F(000) = 1008
Mr = 237.29	Dx = 1.248 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2437 reflections
a = 17.6363 (14) Å	θ = 2.4–27.5°
b = 10.7968 (9) Å	µ = 0.08 mm−1
c = 13.6308 (9) Å	T = 150 K
β = 103.260 (3)°	Prism, colourless
V = 2526.3 (3) Å3	0.52 × 0.33 × 0.27 mm
Z = 8

Bruker APEXII diffractometer	2279 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −22→22
Tmin = 0.873, Tmax = 0.979	k = −14→10
6746 measured reflections	l = −17→10
2875 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0758P)2 + 2.2919P] where P = (Fo2 + 2Fc2)/3
2875 reflections	(Δ/σ)max = 0.001
167 parameters	Δρmax = 0.69 e Å−3
0 restraints	Δρmin = −0.28 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
C2	0.58114 (9)	0.12806 (16)	0.08077 (12)	0.0263 (4)
H2	0.5264	0.0972	0.0596	0.032*
C3	0.58821 (10)	0.24612 (15)	0.02362 (12)	0.0260 (4)
C4	0.52341 (10)	0.29679 (18)	−0.03934 (14)	0.0346 (4)
H4	0.4744	0.2568	−0.0469	0.042*
C5	0.52839 (11)	0.40454 (19)	−0.09163 (15)	0.0378 (4)
H5	0.4824	0.438	−0.1337	0.045*
C6	0.59864 (10)	0.46561 (16)	−0.08463 (12)	0.0273 (4)
C7	0.60403 (12)	0.58261 (18)	−0.14265 (15)	0.0402 (5)
H7A	0.6587	0.608	−0.1317	0.06*
H7B	0.574	0.6483	−0.1194	0.06*
H7C	0.5829	0.5677	−0.2147	0.06*
C8	0.66448 (9)	0.41410 (17)	−0.02209 (12)	0.0281 (4)
H8	0.7136	0.4532	−0.0161	0.034*
C9	0.65959 (10)	0.30599 (17)	0.03197 (12)	0.0295 (4)
H9	0.7052	0.2727	0.0749	0.035*
C10	0.60048 (10)	0.14901 (16)	0.19407 (11)	0.0284 (4)
H10A	0.6503	0.1948	0.2132	0.034*
H10B	0.5595	0.2018	0.2113	0.034*
C11	0.60719 (10)	0.03170 (16)	0.25526 (12)	0.0269 (4)
C13	0.63292 (9)	−0.07957 (16)	0.21014 (11)	0.0233 (3)
C14	0.64681 (10)	−0.19096 (17)	0.26412 (12)	0.0296 (4)
H14	0.6365	−0.1956	0.3294	0.035*
C15	0.67503 (10)	−0.29353 (17)	0.22452 (13)	0.0312 (4)
H15	0.6843	−0.3684	0.262	0.037*
C16	0.68997 (9)	−0.28610 (16)	0.12829 (13)	0.0287 (4)
H16	0.7099	−0.3564	0.1007	0.034*
C17	0.67624 (9)	−0.17860 (16)	0.07284 (12)	0.0253 (4)
H17	0.6868	−0.1755	0.0076	0.03*
C18	0.64660 (8)	−0.07303 (15)	0.11196 (11)	0.0206 (3)
N1	0.63337 (8)	0.03393 (13)	0.05626 (10)	0.0229 (3)
H1N	0.6284 (11)	0.0219 (18)	−0.0085 (16)	0.028*
O12	0.59607 (9)	0.03372 (13)	0.34096 (9)	0.0416 (4)

	U11	U22	U33	U12	U13	U23
C2	0.0283 (8)	0.0280 (9)	0.0236 (8)	−0.0016 (7)	0.0076 (6)	−0.0007 (6)
C3	0.0363 (9)	0.0234 (8)	0.0213 (7)	0.0002 (7)	0.0130 (6)	−0.0022 (6)
C4	0.0292 (8)	0.0348 (10)	0.0393 (10)	−0.0087 (7)	0.0068 (7)	0.0020 (8)
C5	0.0291 (9)	0.0382 (11)	0.0413 (10)	−0.0014 (8)	−0.0018 (7)	0.0088 (8)
C6	0.0341 (9)	0.0227 (8)	0.0257 (8)	−0.0020 (7)	0.0080 (6)	−0.0003 (6)
C7	0.0520 (11)	0.0280 (10)	0.0395 (10)	−0.0034 (8)	0.0084 (8)	0.0063 (8)
C8	0.0237 (7)	0.0313 (9)	0.0301 (8)	−0.0046 (7)	0.0075 (6)	−0.0040 (7)
C9	0.0291 (8)	0.0331 (10)	0.0252 (8)	0.0069 (7)	0.0042 (6)	0.0009 (7)
C10	0.0406 (9)	0.0267 (9)	0.0198 (7)	0.0029 (7)	0.0110 (7)	−0.0022 (6)
C11	0.0333 (8)	0.0314 (9)	0.0166 (7)	0.0006 (7)	0.0072 (6)	−0.0006 (6)
C13	0.0255 (7)	0.0265 (8)	0.0179 (7)	−0.0004 (6)	0.0054 (6)	−0.0005 (6)
C14	0.0353 (9)	0.0329 (10)	0.0210 (7)	0.0009 (7)	0.0074 (6)	0.0050 (7)
C15	0.0338 (9)	0.0278 (9)	0.0315 (9)	0.0023 (7)	0.0063 (7)	0.0063 (7)
C16	0.0277 (8)	0.0260 (9)	0.0339 (9)	0.0014 (7)	0.0098 (7)	−0.0027 (7)
C17	0.0265 (8)	0.0277 (9)	0.0238 (7)	−0.0021 (6)	0.0100 (6)	−0.0035 (6)
C18	0.0197 (7)	0.0236 (8)	0.0187 (7)	−0.0041 (6)	0.0047 (5)	−0.0022 (6)
N1	0.0313 (7)	0.0236 (7)	0.0159 (6)	−0.0003 (5)	0.0097 (5)	−0.0013 (5)
O12	0.0695 (10)	0.0406 (8)	0.0189 (6)	0.0102 (7)	0.0186 (6)	0.0020 (5)

C2—N1	1.461 (2)	C10—C11	1.506 (2)
C2—C3	1.514 (2)	C10—H10A	0.99
C2—C10	1.520 (2)	C10—H10B	0.99
C2—H2	1	C11—O12	1.228 (2)
C3—C4	1.376 (2)	C11—C13	1.468 (2)
C3—C9	1.396 (2)	C13—C14	1.402 (2)
C4—C5	1.378 (3)	C13—C18	1.415 (2)
C4—H4	0.95	C14—C15	1.374 (3)
C5—C6	1.387 (2)	C14—H14	0.95
C5—H5	0.95	C15—C16	1.398 (2)
C6—C8	1.389 (2)	C15—H15	0.95
C6—C7	1.505 (2)	C16—C17	1.376 (2)
C7—H7A	0.98	C16—H16	0.95
C7—H7B	0.98	C17—C18	1.409 (2)
C7—H7C	0.98	C17—H17	0.95
C8—C9	1.394 (2)	C18—N1	1.372 (2)
C8—H8	0.95	N1—H1N	0.88 (2)
C9—H9	0.95
N1—C2—C3	109.72 (13)	C11—C10—C2	114.09 (14)
N1—C2—C10	109.24 (13)	C11—C10—H10A	108.7
C3—C2—C10	111.82 (14)	C2—C10—H10A	108.7
N1—C2—H2	108.7	C11—C10—H10B	108.7
C3—C2—H2	108.7	C2—C10—H10B	108.7
C10—C2—H2	108.7	H10A—C10—H10B	107.6
C4—C3—C9	118.11 (15)	O12—C11—C13	123.04 (15)
C4—C3—C2	120.08 (15)	O12—C11—C10	120.15 (15)
C9—C3—C2	121.81 (15)	C13—C11—C10	116.66 (13)
C3—C4—C5	121.08 (16)	C14—C13—C18	119.47 (15)
C3—C4—H4	119.5	C14—C13—C11	121.05 (14)
C5—C4—H4	119.5	C18—C13—C11	119.45 (14)
C4—C5—C6	121.84 (16)	C15—C14—C13	121.38 (15)
C4—C5—H5	119.1	C15—C14—H14	119.3
C6—C5—H5	119.1	C13—C14—H14	119.3
C5—C6—C8	117.36 (16)	C14—C15—C16	119.03 (16)
C5—C6—C7	121.72 (16)	C14—C15—H15	120.5
C8—C6—C7	120.92 (16)	C16—C15—H15	120.5
C6—C7—H7A	109.5	C17—C16—C15	121.09 (16)
C6—C7—H7B	109.5	C17—C16—H16	119.5
H7A—C7—H7B	109.5	C15—C16—H16	119.5
C6—C7—H7C	109.5	C16—C17—C18	120.56 (14)
H7A—C7—H7C	109.5	C16—C17—H17	119.7
H7B—C7—H7C	109.5	C18—C17—H17	119.7
C6—C8—C9	121.02 (15)	N1—C18—C17	120.15 (13)
C6—C8—H8	119.5	N1—C18—C13	121.39 (14)
C9—C8—H8	119.5	C17—C18—C13	118.44 (14)
C8—C9—C3	120.57 (15)	C18—N1—C2	119.67 (12)
C8—C9—H9	119.7	C18—N1—H1N	113.4 (13)
C3—C9—H9	119.7	C2—N1—H1N	114.2 (13)
N1—C2—C3—C4	122.88 (17)	C10—C11—C13—C14	175.01 (15)
C10—C2—C3—C4	−115.76 (17)	O12—C11—C13—C18	−178.14 (16)
N1—C2—C3—C9	−56.54 (19)	C10—C11—C13—C18	−2.7 (2)
C10—C2—C3—C9	64.8 (2)	C18—C13—C14—C15	1.4 (2)
C9—C3—C4—C5	−0.9 (3)	C11—C13—C14—C15	−176.33 (15)
C2—C3—C4—C5	179.62 (17)	C13—C14—C15—C16	−0.1 (3)
C3—C4—C5—C6	1.0 (3)	C14—C15—C16—C17	−0.6 (3)
C4—C5—C6—C8	−0.3 (3)	C15—C16—C17—C18	0.0 (2)
C4—C5—C6—C7	179.37 (18)	C16—C17—C18—N1	179.75 (14)
C5—C6—C8—C9	−0.6 (3)	C16—C17—C18—C13	1.3 (2)
C7—C6—C8—C9	179.79 (16)	C14—C13—C18—N1	179.63 (14)
C6—C8—C9—C3	0.7 (3)	C11—C13—C18—N1	−2.6 (2)
C4—C3—C9—C8	0.1 (2)	C14—C13—C18—C17	−1.9 (2)
C2—C3—C9—C8	179.54 (15)	C11—C13—C18—C17	175.80 (14)
N1—C2—C10—C11	−48.91 (19)	C17—C18—N1—C2	160.66 (14)
C3—C2—C10—C11	−170.55 (14)	C13—C18—N1—C2	−20.9 (2)
C2—C10—C11—O12	−155.13 (16)	C3—C2—N1—C18	168.89 (13)
C2—C10—C11—C13	29.3 (2)	C10—C2—N1—C18	45.99 (19)
O12—C11—C13—C14	−0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O12i	0.88 (2)	2.09 (2)	2.9484 (17)	166.9 (18)
C4—H4···Cg1ii	0.95	2.70	3.546 (2)	149
C14—H14···Cg2iii	0.95	2.80	3.617 (2)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C13–C18 and C3–C9 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O12i	0.88 (2)	2.09 (2)	2.9484 (17)	166.9 (18)
C4—H4⋯Cg1ii	0.95	2.70	3.546 (2)	149
C14—H14⋯Cg2iii	0.95	2.80	3.617 (2)	144

Symmetry codes: (i) ; (ii) ; (iii) .