1-(3-Ethyl-phen-yl)-4,6-dimethyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile.

In the title compound, C(16)H(16)N(2)O, the essentially planar 1,2-dihydro-pyridine ring [maximum deviation = 0.021 (1) Å] makes a dihedral angle of 85.33 (8)° with the benzene ring. In the crystal, mol-ecules are linked into a chain along the b axis via C-H⋯O inter-actions.

Related literature

For the biological activities and applications of 2-pyridone derivatives, see: Abadi et al. (2009 ▶); Cheney et al. (2007 ▶); Aqui & Vonderheide (2008 ▶); Ambrosini et al. (1997 ▶); Murata et al. (2001 ▶); Ghorab et al. (2009 ▶, 2010 ▶); Al-Said et al. (2010 ▶). For related structures, see: Lynch & McClenaghan (2002 ▶); Elgemeie & Jones (2004 ▶).

Experimental

Crystal data

C16H16N2O

M = 252.31

Monoclinic,

a = 8.3834 (3) Å

b = 7.1852 (2) Å

c = 23.5264 (8) Å

β = 93.203 (3)°

V = 1414.93 (8) Å3

Z = 4

Cu Kα radiation

μ = 0.59 mm−1

T = 296 K

0.93 × 0.46 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.609, T max = 0.960

9742 measured reflections

2638 independent reflections

1938 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.161

S = 1.09

2638 reflections

170 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812019927/is5134sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019927/is5134Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812019927/is5134Isup3.cml

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

C16H16N2O	F(000) = 536
Mr = 252.31	Dx = 1.184 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 1728 reflections
a = 8.3834 (3) Å	θ = 3.8–62.6°
b = 7.1852 (2) Å	µ = 0.59 mm−1
c = 23.5264 (8) Å	T = 296 K
β = 93.203 (3)°	Plate, colorless
V = 1414.93 (8) Å3	0.93 × 0.46 × 0.07 mm
Z = 4

Bruker APEXII CCD diffractometer	2638 independent reflections
Radiation source: fine-focus sealed tube	1938 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 69.8°, θmin = 3.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.609, Tmax = 0.960	k = −6→8
9742 measured reflections	l = −28→28

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.161	w = 1/[σ2(Fo2) + (0.0972P)2 + 0.0312P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
2638 reflections	Δρmax = 0.30 e Å−3
170 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0026 (7)

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	0.51182 (17)	−0.19353 (15)	0.40553 (6)	0.0771 (4)
N1	0.43401 (15)	0.09675 (17)	0.37682 (6)	0.0565 (4)
N2	0.8174 (2)	−0.1541 (2)	0.51433 (8)	0.0818 (5)
C1	0.52879 (18)	−0.0253 (2)	0.41097 (7)	0.0567 (4)
C2	0.64093 (18)	0.0642 (2)	0.45059 (7)	0.0596 (3)
C3	0.65232 (18)	0.2536 (2)	0.45604 (7)	0.0574 (4)
C4	0.54774 (19)	0.3644 (2)	0.42144 (8)	0.0614 (4)
H4A	0.5523	0.4932	0.4250	0.074*
C5	0.44005 (19)	0.2869 (2)	0.38292 (7)	0.0580 (4)
C6	0.32547 (19)	0.0076 (2)	0.33530 (7)	0.0599 (4)
C7	0.1715 (2)	−0.0320 (2)	0.34863 (8)	0.0687 (5)
H7A	0.1361	0.0037	0.3838	0.082*
C8	0.0682 (2)	−0.1252 (3)	0.30994 (9)	0.0756 (5)
C9	0.1242 (3)	−0.1759 (3)	0.25855 (9)	0.0826 (6)
H9A	0.0571	−0.2395	0.2324	0.099*
C11	0.3787 (2)	−0.0421 (3)	0.28313 (8)	0.0763 (5)
H11A	0.4822	−0.0133	0.2739	0.092*
C12	−0.0998 (3)	−0.1725 (4)	0.32586 (12)	0.1040 (8)
H12A	−0.1475	−0.0635	0.3423	0.125*
H12B	−0.1637	−0.2053	0.2917	0.125*
C13	−0.1029 (3)	−0.3299 (4)	0.36728 (13)	0.1134 (9)
H13A	−0.2115	−0.3566	0.3754	0.170*
H13B	−0.0437	−0.2960	0.4018	0.170*
H13C	−0.0556	−0.4381	0.3512	0.170*
C14	0.73956 (19)	−0.0576 (2)	0.48568 (7)	0.0596 (3)
C15	0.7695 (2)	0.3428 (2)	0.49802 (9)	0.0739 (5)
H15A	0.8759	0.3053	0.4901	0.111*
H15B	0.7470	0.3047	0.5358	0.111*
H15C	0.7607	0.4757	0.4950	0.111*
C16	0.3267 (2)	0.4026 (3)	0.34699 (9)	0.0788 (6)
H16A	0.3524	0.5319	0.3524	0.118*
H16B	0.2196	0.3803	0.3578	0.118*
H16C	0.3350	0.3703	0.3077	0.118*
C10	0.2776 (3)	−0.1347 (3)	0.24493 (9)	0.0876 (6)
H10A	0.3129	−0.1697	0.2097	0.105*

	U11	U22	U33	U12	U13	U23
O1	0.0885 (9)	0.0349 (6)	0.1054 (10)	−0.0021 (5)	−0.0179 (7)	−0.0017 (5)
N1	0.0590 (7)	0.0398 (7)	0.0703 (8)	−0.0013 (5)	0.0004 (6)	0.0012 (5)
N2	0.0869 (11)	0.0633 (10)	0.0934 (12)	0.0139 (8)	−0.0113 (9)	0.0020 (7)
C1	0.0609 (8)	0.0358 (8)	0.0735 (10)	0.0006 (6)	0.0040 (7)	0.0010 (6)
C2	0.0608 (6)	0.0431 (6)	0.0747 (7)	0.0014 (5)	0.0019 (5)	−0.0009 (5)
C3	0.0564 (8)	0.0408 (8)	0.0754 (10)	−0.0031 (6)	0.0078 (7)	−0.0021 (6)
C4	0.0657 (9)	0.0343 (7)	0.0842 (11)	−0.0015 (6)	0.0040 (8)	−0.0001 (7)
C5	0.0611 (9)	0.0393 (8)	0.0740 (10)	0.0006 (6)	0.0066 (7)	0.0047 (6)
C6	0.0643 (9)	0.0441 (8)	0.0708 (10)	0.0003 (7)	−0.0015 (7)	0.0005 (6)
C7	0.0668 (9)	0.0638 (11)	0.0751 (11)	−0.0024 (8)	0.0006 (8)	−0.0010 (8)
C8	0.0698 (10)	0.0683 (11)	0.0872 (13)	−0.0069 (9)	−0.0094 (9)	0.0029 (9)
C9	0.0881 (14)	0.0756 (13)	0.0816 (13)	−0.0042 (9)	−0.0162 (11)	−0.0080 (9)
C11	0.0761 (11)	0.0758 (13)	0.0772 (12)	−0.0043 (9)	0.0074 (9)	−0.0066 (9)
C12	0.0726 (13)	0.117 (2)	0.120 (2)	−0.0191 (12)	−0.0096 (12)	−0.0005 (15)
C13	0.0886 (15)	0.143 (3)	0.1091 (19)	−0.0278 (15)	0.0121 (14)	−0.0044 (16)
C14	0.0608 (6)	0.0431 (6)	0.0747 (7)	0.0014 (5)	0.0019 (5)	−0.0009 (5)
C15	0.0712 (11)	0.0527 (10)	0.0963 (14)	−0.0067 (8)	−0.0075 (9)	−0.0088 (8)
C16	0.0884 (12)	0.0489 (10)	0.0970 (13)	0.0083 (8)	−0.0137 (10)	0.0082 (8)
C10	0.1033 (16)	0.0863 (14)	0.0730 (12)	0.0018 (12)	0.0032 (11)	−0.0142 (10)

O1—C1	1.2233 (18)	C8—C12	1.516 (3)
N1—C5	1.374 (2)	C9—C10	1.375 (3)
N1—C1	1.4050 (19)	C9—H9A	0.9300
N1—C6	1.447 (2)	C11—C10	1.373 (3)
N2—C14	1.145 (2)	C11—H11A	0.9300
C1—C2	1.438 (2)	C12—C13	1.494 (4)
C2—C3	1.369 (2)	C12—H12A	0.9700
C2—C14	1.434 (2)	C12—H12B	0.9700
C3—C4	1.409 (2)	C13—H13A	0.9600
C3—C15	1.498 (2)	C13—H13B	0.9600
C4—C5	1.362 (2)	C13—H13C	0.9600
C4—H4A	0.9300	C15—H15A	0.9600
C5—C16	1.490 (2)	C15—H15B	0.9600
C6—C7	1.375 (2)	C15—H15C	0.9600
C6—C11	1.377 (3)	C16—H16A	0.9600
C7—C8	1.393 (3)	C16—H16B	0.9600
C7—H7A	0.9300	C16—H16C	0.9600
C8—C9	1.371 (3)	C10—H10A	0.9300
C5—N1—C1	122.98 (13)	C10—C11—H11A	120.3
C5—N1—C6	121.91 (13)	C6—C11—H11A	120.3
C1—N1—C6	115.10 (12)	C13—C12—C8	112.4 (2)
O1—C1—N1	119.87 (14)	C13—C12—H12A	109.1
O1—C1—C2	125.29 (14)	C8—C12—H12A	109.1
N1—C1—C2	114.83 (13)	C13—C12—H12B	109.1
C3—C2—C14	121.17 (14)	C8—C12—H12B	109.1
C3—C2—C1	123.00 (14)	H12A—C12—H12B	107.9
C14—C2—C1	115.82 (13)	C12—C13—H13A	109.5
C2—C3—C4	117.99 (14)	C12—C13—H13B	109.5
C2—C3—C15	121.81 (15)	H13A—C13—H13B	109.5
C4—C3—C15	120.19 (14)	C12—C13—H13C	109.5
C5—C4—C3	121.42 (14)	H13A—C13—H13C	109.5
C5—C4—H4A	119.3	H13B—C13—H13C	109.5
C3—C4—H4A	119.3	N2—C14—C2	179.11 (19)
C4—C5—N1	119.66 (14)	C3—C15—H15A	109.5
C4—C5—C16	121.84 (15)	C3—C15—H15B	109.5
N1—C5—C16	118.50 (15)	H15A—C15—H15B	109.5
C7—C6—C11	120.32 (16)	C3—C15—H15C	109.5
C7—C6—N1	120.05 (16)	H15A—C15—H15C	109.5
C11—C6—N1	119.60 (15)	H15B—C15—H15C	109.5
C6—C7—C8	120.54 (18)	C5—C16—H16A	109.5
C6—C7—H7A	119.7	C5—C16—H16B	109.5
C8—C7—H7A	119.7	H16A—C16—H16B	109.5
C9—C8—C7	118.25 (18)	C5—C16—H16C	109.5
C9—C8—C12	121.81 (19)	H16A—C16—H16C	109.5
C7—C8—C12	119.9 (2)	H16B—C16—H16C	109.5
C8—C9—C10	121.29 (19)	C11—C10—C9	120.2 (2)
C8—C9—H9A	119.4	C11—C10—H10A	119.9
C10—C9—H9A	119.4	C9—C10—H10A	119.9
C10—C11—C6	119.37 (18)
C5—N1—C1—O1	176.08 (15)	C1—N1—C5—C16	−176.04 (16)
C6—N1—C1—O1	−2.4 (2)	C6—N1—C5—C16	2.3 (2)
C5—N1—C1—C2	−3.9 (2)	C5—N1—C6—C7	−85.9 (2)
C6—N1—C1—C2	177.62 (13)	C1—N1—C6—C7	92.63 (18)
O1—C1—C2—C3	−178.23 (16)	C5—N1—C6—C11	96.09 (19)
N1—C1—C2—C3	1.7 (2)	C1—N1—C6—C11	−85.41 (19)
O1—C1—C2—C14	0.4 (3)	C11—C6—C7—C8	0.9 (3)
N1—C1—C2—C14	−179.68 (14)	N1—C6—C7—C8	−177.12 (16)
C14—C2—C3—C4	−177.87 (15)	C6—C7—C8—C9	0.0 (3)
C1—C2—C3—C4	0.6 (2)	C6—C7—C8—C12	178.37 (19)
C14—C2—C3—C15	1.0 (3)	C7—C8—C9—C10	−0.7 (3)
C1—C2—C3—C15	179.52 (16)	C12—C8—C9—C10	−179.0 (2)
C2—C3—C4—C5	−1.1 (2)	C7—C6—C11—C10	−1.2 (3)
C15—C3—C4—C5	179.98 (16)	N1—C6—C11—C10	176.86 (17)
C3—C4—C5—N1	−0.9 (2)	C9—C8—C12—C13	104.2 (3)
C3—C4—C5—C16	178.71 (16)	C7—C8—C12—C13	−74.1 (3)
C1—N1—C5—C4	3.6 (2)	C6—C11—C10—C9	0.5 (3)
C6—N1—C5—C4	−178.01 (15)	C8—C9—C10—C11	0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O1i	0.93	2.32	3.2105 (18)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O1i	0.93	2.32	3.2105 (18)	161

Symmetry code: (i) .