4-Methyl-1-phenyl-quinolin-2(1H)-one.

In the title compound, C(16)H(13)NO, the mol-ecules are connected three-dimensionally through non-classical C-H⋯O and C-H⋯π inter-actions of 3.272 (3), 3.380 (3) and 3.382 (4) Å. Classical hydrogen bonds are not observed. The dihedral angle between the benzyl and quinolin-2(1H)-one mean planes is 87.15 (7)°

Related literature

For related literature, see: Bondensgaard & Jacobsen (1999 ▶); Fürstenberg et al. (2006 ▶); Kovalska et al. (2006 ▶); Martínez & Chacón-García (2005 ▶); Perekalin & Lerner (1951 ▶); Rajnikant et al. (2002 ▶); Schenkel & Aeberli (1957 ▶); Shishkina et al. (2005 ▶); Staerk et al. (1997 ▶); Vasilev et al. (2005 ▶); Vincente et al. (2005 ▶); Zipper et al. (2004 ▶); Sheldrick & Morr (1981 ▶).

Experimental

Crystal data

C16H13NO

M = 235.27

Monoclinic,

a = 8.984 (2) Å

b = 14.194 (4) Å

c = 10.1785 (16) Å

β = 106.631 (15)°

V = 1243.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 290 (2) K

0.31 × 0.31 × 0.31 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

6212 measured reflections

2991 independent reflections

1351 reflections with I > 2σ(I)

R int = 0.053

3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.160

S = 0.97

2991 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); Mercury (Bruno et al., 2002 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807061727/pr2017sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061727/pr2017Isup2.hkl

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

C16H13NO	F000 = 496
Mr = 235.27	Dx = 1.256 Mg m−3
Monoclinic, P21/c	Melting point: not measured K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 8.984 (2) Å	Cell parameters from 22 reflections
b = 14.194 (4) Å	θ = 18.2–19.3º
c = 10.1785 (16) Å	µ = 0.08 mm−1
β = 106.631 (15)º	T = 290 (2) K
V = 1243.7 (5) Å3	Cubic, pale yellow
Z = 4	0.31 × 0.31 × 0.31 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.053
Radiation source: fine-focus sealed tube	θmax = 28.0º
Monochromator: graphite	θmin = 2.4º
T = 290(2) K	h = 0→11
non–profiled ω/2θ scans	k = −18→18
Absorption correction: none	l = −13→12
6212 measured reflections	3 standard reflections
2991 independent reflections	every 120 min
1351 reflections with I > 2σ(I)	intensity decay: none

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055	H-atom parameters constrained
wR(F2) = 0.160	w = 1/[σ2(Fo2) + (0.0699P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max < 0.001
2991 reflections	Δρmax = 0.15 e Å−3
164 parameters	Δρmin = −0.16 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.7036 (2)	0.45463 (12)	0.80663 (18)	0.0468 (5)
C1	0.5505 (2)	0.46557 (16)	0.8116 (2)	0.0443 (5)
C6	0.4822 (3)	0.39507 (15)	0.8725 (2)	0.0448 (5)
O1	0.9282 (2)	0.37000 (13)	0.8539 (2)	0.0763 (6)
C2	0.4652 (3)	0.54564 (16)	0.7571 (2)	0.0500 (6)
H2	0.5194	0.5981	0.7165	0.060*
C11	0.7750 (2)	0.52552 (15)	0.7433 (2)	0.0461 (6)
C5	0.3277 (3)	0.40691 (18)	0.8733 (2)	0.0535 (6)
H5	0.2882	0.3524	0.9123	0.064*
C4	0.2438 (3)	0.48561 (19)	0.8192 (2)	0.0580 (7)
H4	0.1196	0.4968	0.8047	0.070*
C10	0.7938 (3)	0.37699 (17)	0.8615 (3)	0.0554 (6)
C9	0.7218 (3)	0.30818 (17)	0.9274 (2)	0.0580 (7)
H9	0.7825	0.2518	0.9753	0.070*
C3	0.3150 (3)	0.55537 (17)	0.7623 (2)	0.0570 (6)
H3	0.2571	0.6117	0.7295	0.068*
C7	0.5753 (3)	0.31498 (16)	0.9346 (2)	0.0519 (6)
C8	0.5092 (3)	0.24147 (17)	1.0075 (3)	0.0711 (8)
H8B	0.4706	0.2655	1.0736	0.107*
H8C	0.5783	0.1853	1.0437	0.107*
H8A	0.4026	0.2090	0.9385	0.107*
C16	0.7687 (3)	0.51761 (18)	0.6074 (3)	0.0632 (7)
H16	0.7009	0.4576	0.5534	0.076*
C13	0.9139 (3)	0.67027 (18)	0.7559 (3)	0.0639 (7)
H13	0.9747	0.7274	0.8167	0.077*
C14	0.9077 (3)	0.66239 (19)	0.6202 (3)	0.0627 (7)
H14	0.9663	0.7190	0.5738	0.075*
C12	0.8477 (3)	0.60141 (18)	0.8181 (3)	0.0586 (7)
H12	0.8565	0.5980	0.8999	0.070*
C15	0.8372 (3)	0.5863 (2)	0.5463 (3)	0.0730 (8)
H15	0.8372	0.5753	0.4416	0.109 (10)*

	U11	U22	U33	U12	U13	U23
N1	0.0390 (10)	0.0453 (11)	0.0582 (12)	0.0007 (9)	0.0173 (9)	0.0040 (9)
C1	0.0376 (12)	0.0499 (13)	0.0448 (13)	−0.0019 (10)	0.0110 (10)	−0.0053 (11)
C6	0.0473 (13)	0.0437 (13)	0.0441 (12)	−0.0056 (11)	0.0144 (10)	−0.0078 (10)
O1	0.0509 (11)	0.0703 (12)	0.1140 (16)	0.0136 (9)	0.0336 (11)	0.0111 (11)
C2	0.0456 (13)	0.0505 (14)	0.0537 (14)	0.0008 (11)	0.0138 (11)	0.0035 (11)
C11	0.0373 (11)	0.0462 (14)	0.0563 (14)	−0.0004 (10)	0.0154 (11)	−0.0018 (11)
C5	0.0496 (14)	0.0584 (15)	0.0568 (15)	−0.0079 (12)	0.0222 (12)	−0.0046 (12)
C4	0.0417 (13)	0.0720 (17)	0.0621 (16)	0.0004 (13)	0.0179 (12)	−0.0039 (14)
C10	0.0476 (14)	0.0510 (14)	0.0680 (16)	0.0056 (12)	0.0173 (12)	−0.0013 (12)
C9	0.0574 (15)	0.0450 (14)	0.0702 (17)	0.0051 (12)	0.0162 (13)	0.0018 (12)
C3	0.0446 (14)	0.0624 (16)	0.0616 (15)	0.0084 (12)	0.0115 (12)	0.0027 (13)
C7	0.0576 (15)	0.0430 (14)	0.0558 (14)	−0.0060 (12)	0.0176 (12)	−0.0063 (11)
C8	0.085 (2)	0.0497 (15)	0.0871 (19)	−0.0027 (14)	0.0388 (17)	0.0077 (14)
C16	0.0760 (18)	0.0561 (15)	0.0619 (17)	−0.0119 (14)	0.0268 (14)	−0.0051 (13)
C13	0.0516 (15)	0.0549 (15)	0.0838 (19)	−0.0149 (12)	0.0171 (14)	−0.0095 (14)
C14	0.0551 (15)	0.0554 (16)	0.084 (2)	−0.0032 (13)	0.0309 (14)	0.0065 (14)
C12	0.0526 (14)	0.0634 (16)	0.0614 (15)	−0.0088 (13)	0.0187 (12)	−0.0081 (13)
C15	0.093 (2)	0.0674 (18)	0.0687 (18)	−0.0083 (17)	0.0392 (17)	−0.0007 (15)

N1—C10	1.387 (3)	C9—C7	1.342 (3)
N1—C1	1.400 (3)	C9—H9	1.0118
N1—C11	1.441 (3)	C3—H3	0.9603
C1—C2	1.394 (3)	C7—C8	1.499 (3)
C1—C6	1.407 (3)	C8—H8B	0.9069
C6—C5	1.401 (3)	C8—H8C	1.0133
C6—C7	1.445 (3)	C8—H8A	1.1127
O1—C10	1.236 (3)	C16—C15	1.391 (4)
C2—C3	1.373 (3)	C16—H16	1.0983
C2—H2	1.0382	C13—C14	1.371 (3)
C11—C12	1.372 (3)	C13—C12	1.387 (3)
C11—C16	1.372 (3)	C13—H13	1.0707
C5—C4	1.372 (3)	C14—C15	1.364 (4)
C5—H5	0.9818	C14—H14	1.1348
C4—C3	1.392 (3)	C12—H12	0.8147
C4—H4	1.0949	C15—H15	1.0773
C10—C9	1.439 (3)
C10—N1—C1	122.73 (19)	C2—C3—C4	121.2 (2)
C10—N1—C11	116.83 (18)	C2—C3—H3	120.7
C1—N1—C11	120.44 (18)	C4—C3—H3	118.0
C2—C1—N1	120.7 (2)	C9—C7—C6	119.1 (2)
C2—C1—C6	119.7 (2)	C9—C7—C8	120.7 (2)
N1—C1—C6	119.6 (2)	C6—C7—C8	120.2 (2)
C5—C6—C1	118.4 (2)	C7—C8—H8B	113.3
C5—C6—C7	122.8 (2)	C7—C8—H8C	116.1
C1—C6—C7	118.8 (2)	H8B—C8—H8C	110.5
C3—C2—C1	120.1 (2)	C7—C8—H8A	111.6
C3—C2—H2	121.5	H8B—C8—H8A	100.4
C1—C2—H2	118.4	H8C—C8—H8A	103.3
C12—C11—C16	120.0 (2)	C11—C16—C15	119.8 (2)
C12—C11—N1	120.1 (2)	C11—C16—H16	115.2
C16—C11—N1	119.9 (2)	C15—C16—H16	124.9
C4—C5—C6	121.8 (2)	C14—C13—C12	120.2 (2)
C4—C5—H5	125.7	C14—C13—H13	120.7
C6—C5—H5	112.4	C12—C13—H13	119.0
C5—C4—C3	118.8 (2)	C15—C14—C13	119.9 (2)
C5—C4—H4	126.5	C15—C14—H14	121.9
C3—C4—H4	114.3	C13—C14—H14	118.2
O1—C10—N1	120.5 (2)	C11—C12—C13	119.9 (2)
O1—C10—C9	123.6 (2)	C11—C12—H12	114.3
N1—C10—C9	116.0 (2)	C13—C12—H12	125.4
C7—C9—C10	123.7 (2)	C14—C15—C16	120.3 (3)
C7—C9—H9	115.6	C14—C15—H15	121.9
C10—C9—H9	120.6	C16—C15—H15	117.8
C10—N1—C1—C2	178.9 (2)	C11—N1—C10—C9	178.5 (2)
C11—N1—C1—C2	−0.8 (3)	O1—C10—C9—C7	−179.2 (2)
C10—N1—C1—C6	−1.0 (3)	N1—C10—C9—C7	1.6 (4)
C11—N1—C1—C6	179.3 (2)	C1—C2—C3—C4	−1.2 (4)
C2—C1—C6—C5	1.5 (3)	C5—C4—C3—C2	1.4 (4)
N1—C1—C6—C5	−178.6 (2)	C10—C9—C7—C6	0.5 (4)
C2—C1—C6—C7	−176.9 (2)	C10—C9—C7—C8	−178.7 (2)
N1—C1—C6—C7	3.0 (3)	C5—C6—C7—C9	178.9 (2)
N1—C1—C2—C3	179.8 (2)	C1—C6—C7—C9	−2.8 (3)
C6—C1—C2—C3	−0.3 (3)	C5—C6—C7—C8	−1.9 (3)
C10—N1—C11—C12	−93.2 (2)	C1—C6—C7—C8	176.4 (2)
C1—N1—C11—C12	86.6 (3)	C12—C11—C16—C15	0.5 (4)
C10—N1—C11—C16	87.5 (3)	N1—C11—C16—C15	179.7 (2)
C1—N1—C11—C16	−92.7 (3)	C12—C13—C14—C15	−0.4 (4)
C1—C6—C5—C4	−1.3 (3)	C16—C11—C12—C13	0.4 (4)
C7—C6—C5—C4	177.0 (2)	N1—C11—C12—C13	−178.9 (2)
C6—C5—C4—C3	−0.1 (4)	C14—C13—C12—C11	−0.4 (4)
C1—N1—C10—O1	179.5 (2)	C13—C14—C15—C16	1.3 (4)
C11—N1—C10—O1	−0.7 (3)	C11—C16—C15—C14	−1.3 (4)
C1—N1—C10—C9	−1.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1i	1.13	2.37	3.272 (3)	135
C4—H4···O1ii	1.09	2.63	3.380 (3)	125
C8—H8A···Cg1iii	1.11	2.73	3.382 (4)	165

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O1i	1.13	2.37	3.272 (3)	135
C4—H4⋯O1ii	1.09	2.63	3.380 (3)	125
C8—H8A⋯Cg1iii	1.11	2.73	3.382 (4)	165

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