8-Methyl-2-oxo-4-(thio-phen-2-yl)-1,2,5,6,7,8-hexa-hydro-quinoline-3-carbonitrile.

In the title compound, C(15)H(14)N(2)OS, the pyridinone ring in the fused-ring system is nearly planar (r.m.s. deviation = 0.011 Å) and the cyclo-hexene ring has a twisted half-boat conformation with the methyl-ene C atom adjacent to the methine C atom deviating by 0.592 (7) Å from the plane defined by the remaining five atoms (r.m.s. deviation = 0.108 Å). The thienyl ring is disordered over two almost coplanar positions of opposite orientation in a 0.649 (4):0.351 (4) ratio, and forms dihedral angles of 51.4 (3) (major component) and 54.2 (3)°, respectively, with the pyridinone ring. In the crystal, inversion-related mol-ecules associate via an eight-membered {⋯HNCO}(2) synthon and these are linked into a linear supra-molecular chain along the a axis by weak π-π inter-actions that occur between centrosymmetrically related pyridinone rings [centroid-centroid distance = 3.889 (2) Å].

Related literature

For background to the cardiotonic and anti-inflammatory properties of this class of compounds, see: Behit & Baraka (2005 ▶); Girgis et al. (2007 ▶). For a related structure, see: Asiri et al. (2011 ▶).

Experimental

Crystal data

C15H14N2OS

M = 270.34

Triclinic,

a = 7.6443 (3) Å

b = 9.6909 (5) Å

c = 9.9852 (5) Å

α = 67.003 (5)°

β = 80.869 (4)°

γ = 76.108 (4)°

V = 659.26 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 100 K

0.30 × 0.20 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.798, T max = 1.000

9707 measured reflections

3041 independent reflections

2356 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.088

wR(F 2) = 0.230

S = 1.07

3041 reflections

185 parameters

33 restraints

H-atom parameters constrained

Δρmax = 1.02 e Å−3

Δρmin = −0.78 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681202836X/xu5572sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202836X/xu5572Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202836X/xu5572Isup3.cml

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

C15H14N2OS	Z = 2
Mr = 270.34	F(000) = 284
Triclinic, P1	Dx = 1.362 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6443 (3) Å	Cell parameters from 3729 reflections
b = 9.6909 (5) Å	θ = 2.3–27.5°
c = 9.9852 (5) Å	µ = 0.24 mm−1
α = 67.003 (5)°	T = 100 K
β = 80.869 (4)°	Plate, yellow
γ = 76.108 (4)°	0.30 × 0.20 × 0.05 mm
V = 659.26 (5) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	3041 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2356 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.031
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.3°
ω scan	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −12→12
Tmin = 0.798, Tmax = 1.000	l = −12→12
9707 measured 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)] = 0.088	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.230	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0899P)2 + 1.5187P] where P = (Fo2 + 2Fc2)/3
3041 reflections	(Δ/σ)max = 0.001
185 parameters	Δρmax = 1.02 e Å−3
33 restraints	Δρmin = −0.78 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	Occ. (<1)
O1	0.8432 (4)	0.6552 (5)	0.4105 (4)	0.0607 (13)
N1	0.7871 (4)	0.4615 (4)	0.6240 (4)	0.0359 (9)
H1n	0.8984	0.4118	0.6160	0.043*
N2	0.4540 (5)	0.9325 (4)	0.3270 (4)	0.0359 (9)
C1	0.9207 (6)	0.2563 (6)	0.9181 (5)	0.0405 (11)
H1A	1.0051	0.3102	0.8423	0.061*
H1B	0.9847	0.1546	0.9765	0.061*
H1C	0.8702	0.3144	0.9813	0.061*
C2	0.7691 (5)	0.2402 (5)	0.8473 (4)	0.0303 (9)
H2	0.8246	0.1755	0.7884	0.036*
C3	0.6307 (6)	0.1585 (5)	0.9600 (5)	0.0337 (10)
H3A	0.5668	0.1120	0.9147	0.040*
H3B	0.6941	0.0752	1.0422	0.040*
C4	0.4947 (6)	0.2674 (5)	1.0173 (5)	0.0361 (10)
H4A	0.5584	0.3154	1.0611	0.043*
H4B	0.4121	0.2101	1.0945	0.043*
C5	0.3854 (5)	0.3914 (5)	0.8953 (4)	0.0300 (9)
H5A	0.3015	0.3458	0.8667	0.036*
H5B	0.3120	0.4703	0.9318	0.036*
C6	0.5042 (5)	0.4659 (4)	0.7629 (4)	0.0219 (7)
C7	0.6793 (5)	0.3935 (4)	0.7432 (4)	0.0244 (8)
C8	0.7363 (5)	0.6006 (5)	0.5159 (5)	0.0367 (11)
C9	0.5537 (5)	0.6763 (4)	0.5364 (4)	0.0252 (8)
C10	0.4413 (5)	0.6133 (4)	0.6569 (4)	0.0204 (7)
C11	0.4972 (5)	0.8193 (5)	0.4214 (4)	0.0258 (8)
C12	0.2592 (5)	0.7030 (4)	0.6738 (4)	0.0311 (9)
S1	0.0646 (2)	0.6528 (2)	0.7033 (2)	0.0426 (7)	0.649 (4)
S1'	0.2014 (7)	0.8647 (5)	0.6683 (4)	0.043*	0.351 (4)
C13	0.260 (2)	0.8772 (14)	0.6570 (7)	0.069 (4)	0.649 (4)
H13	0.3559	0.9306	0.6399	0.082*	0.649 (4)
C13'	0.079 (2)	0.627 (2)	0.6905 (12)	0.069*	0.351 (4)
H13'	0.0714	0.5285	0.6971	0.082*	0.351 (4)
C14	0.0544 (12)	0.9255 (9)	0.6783 (8)	0.0461 (18)	0.649 (4)
H14	0.0031	1.0261	0.6752	0.055*	0.649 (4)
C14'	−0.072 (2)	0.7647 (18)	0.6921 (14)	0.046*	0.351 (4)
H14'	−0.1961	0.7600	0.6992	0.055*	0.351 (4)
C15	−0.0505 (11)	0.8293 (9)	0.7006 (7)	0.0432 (18)	0.649 (4)
H15	−0.1783	0.8545	0.7141	0.052*	0.649 (4)
C15'	−0.0217 (15)	0.8881 (17)	0.6833 (11)	0.043*	0.351 (4)
H15'	−0.1023	0.9788	0.6852	0.052*	0.351 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0203 (15)	0.071 (3)	0.0354 (18)	0.0116 (15)	0.0094 (13)	0.0234 (17)
N1	0.0157 (15)	0.041 (2)	0.0255 (18)	0.0083 (14)	0.0040 (13)	0.0050 (15)
N2	0.0270 (18)	0.035 (2)	0.0275 (18)	0.0013 (15)	−0.0005 (14)	0.0029 (15)
C1	0.026 (2)	0.045 (3)	0.031 (2)	−0.0043 (18)	−0.0045 (17)	0.0055 (19)
C2	0.026 (2)	0.027 (2)	0.025 (2)	0.0028 (15)	−0.0006 (15)	−0.0016 (16)
C3	0.031 (2)	0.0230 (19)	0.032 (2)	−0.0038 (16)	−0.0018 (17)	0.0049 (16)
C4	0.030 (2)	0.034 (2)	0.025 (2)	−0.0049 (17)	0.0056 (16)	0.0047 (17)
C5	0.0189 (18)	0.030 (2)	0.029 (2)	−0.0054 (15)	0.0050 (15)	0.0000 (16)
C6	0.0180 (17)	0.0239 (18)	0.0205 (17)	−0.0050 (13)	−0.0003 (13)	−0.0046 (14)
C7	0.0197 (17)	0.0267 (19)	0.0202 (17)	−0.0022 (14)	0.0012 (13)	−0.0039 (15)
C8	0.0157 (18)	0.045 (2)	0.024 (2)	0.0044 (16)	0.0023 (14)	0.0071 (18)
C9	0.0174 (17)	0.0285 (19)	0.0209 (18)	−0.0013 (14)	−0.0021 (13)	−0.0013 (15)
C10	0.0151 (16)	0.0236 (17)	0.0213 (17)	−0.0047 (13)	−0.0007 (13)	−0.0067 (14)
C11	0.0164 (17)	0.031 (2)	0.0221 (18)	−0.0023 (14)	0.0006 (13)	−0.0034 (16)
C12	0.0238 (19)	0.035 (2)	0.0189 (18)	0.0049 (16)	0.0027 (14)	−0.0018 (16)
S1	0.0090 (7)	0.0483 (10)	0.0447 (10)	−0.0033 (6)	−0.0002 (5)	0.0084 (7)
C13	0.069 (4)	0.069 (4)	0.068 (4)	−0.0132 (15)	−0.0044 (13)	−0.0250 (18)
C14	0.046 (2)	0.045 (2)	0.043 (2)	−0.0018 (12)	0.0006 (12)	−0.0171 (13)
C15	0.040 (2)	0.042 (2)	0.041 (2)	−0.0030 (12)	0.0010 (12)	−0.0128 (13)

O1—C8	1.246 (5)	C6—C10	1.429 (5)
N1—C7	1.366 (5)	C8—C9	1.436 (5)
N1—C8	1.371 (5)	C9—C10	1.381 (5)
N1—H1n	0.8800	C9—C11	1.433 (5)
N2—C11	1.148 (5)	C10—C12	1.477 (5)
C1—C2	1.516 (6)	C12—S1'	1.503 (5)
C1—H1A	0.9800	C12—S1	1.622 (4)
C1—H1B	0.9800	C12—C13	1.632 (13)
C1—H1C	0.9800	C12—C13'	1.668 (17)
C2—C7	1.513 (5)	S1—C15	1.717 (8)
C2—C3	1.530 (5)	S1'—C15'	1.656 (11)
C2—H2	1.0000	C13—C14	1.537 (15)
C3—C4	1.510 (6)	C13—H13	0.9500
C3—H3A	0.9900	C13'—C14'	1.541 (18)
C3—H3B	0.9900	C13'—H13'	0.9500
C4—C5	1.524 (6)	C14—C15	1.304 (12)
C4—H4A	0.9900	C14—H14	0.9500
C4—H4B	0.9900	C14'—C15'	1.309 (15)
C5—C6	1.511 (5)	C14'—H14'	0.9500
C5—H5A	0.9900	C15—H15	0.9500
C5—H5B	0.9900	C15'—H15'	0.9500
C6—C7	1.377 (5)
C7—N1—C8	125.4 (3)	O1—C8—N1	121.6 (4)
C7—N1—H1n	117.3	O1—C8—C9	124.0 (4)
C8—N1—H1n	117.3	N1—C8—C9	114.4 (3)
C2—C1—H1A	109.5	C10—C9—C11	123.1 (3)
C2—C1—H1B	109.5	C10—C9—C8	122.1 (3)
H1A—C1—H1B	109.5	C11—C9—C8	114.9 (3)
C2—C1—H1C	109.5	C9—C10—C6	119.8 (3)
H1A—C1—H1C	109.5	C9—C10—C12	118.5 (3)
H1B—C1—H1C	109.5	C6—C10—C12	121.7 (3)
C7—C2—C1	111.3 (4)	N2—C11—C9	178.5 (4)
C7—C2—C3	111.3 (3)	C10—C12—S1'	130.3 (4)
C1—C2—C3	112.2 (4)	C10—C12—S1	129.1 (3)
C7—C2—H2	107.3	S1'—C12—S1	100.5 (3)
C1—C2—H2	107.3	C10—C12—C13	113.3 (6)
C3—C2—H2	107.3	S1—C12—C13	117.5 (6)
C4—C3—C2	111.4 (3)	C10—C12—C13'	119.2 (8)
C4—C3—H3A	109.4	S1'—C12—C13'	110.3 (8)
C2—C3—H3A	109.4	C13—C12—C13'	127.1 (11)
C4—C3—H3B	109.4	C12—S1—C15	92.6 (4)
C2—C3—H3B	109.4	C12—S1'—C15'	102.2 (6)
H3A—C3—H3B	108.0	C14—C13—C12	95.8 (9)
C3—C4—C5	110.8 (4)	C14—C13—H13	132.1
C3—C4—H4A	109.5	C12—C13—H13	132.1
C5—C4—H4A	109.5	C14'—C13'—C12	99.6 (13)
C3—C4—H4B	109.5	C14'—C13'—H13'	130.2
C5—C4—H4B	109.5	C12—C13'—H13'	130.2
H4A—C4—H4B	108.1	C15—C14—C13	120.5 (8)
C6—C5—C4	112.3 (3)	C15—C14—H14	119.8
C6—C5—H5A	109.2	C13—C14—H14	119.8
C4—C5—H5A	109.2	C15'—C14'—C13'	117.0 (15)
C6—C5—H5B	109.2	C15'—C14'—H14'	121.5
C4—C5—H5B	109.2	C13'—C14'—H14'	121.5
H5A—C5—H5B	107.9	C14—C15—S1	113.6 (6)
C7—C6—C10	118.1 (3)	C14—C15—H15	123.2
C7—C6—C5	120.2 (3)	S1—C15—H15	123.2
C10—C6—C5	121.7 (3)	C14'—C15'—S1'	110.9 (12)
N1—C7—C6	120.2 (3)	C14'—C15'—H15'	124.6
N1—C7—C2	114.9 (3)	S1'—C15'—H15'	124.6
C6—C7—C2	124.9 (3)
C7—C2—C3—C4	−42.7 (5)	C9—C10—C12—S1'	−51.3 (6)
C1—C2—C3—C4	82.7 (5)	C6—C10—C12—S1'	127.3 (4)
C2—C3—C4—C5	62.8 (5)	C9—C10—C12—S1	128.4 (4)
C3—C4—C5—C6	−49.6 (5)	C6—C10—C12—S1	−52.9 (5)
C4—C5—C6—C7	19.3 (6)	C9—C10—C12—C13	−50.5 (4)
C4—C5—C6—C10	−159.4 (4)	C6—C10—C12—C13	128.2 (4)
C8—N1—C7—C6	−0.6 (7)	C9—C10—C12—C13'	123.6 (5)
C8—N1—C7—C2	−179.4 (4)	C6—C10—C12—C13'	−57.7 (5)
C10—C6—C7—N1	−0.8 (6)	C10—C12—S1—C15	−178.7 (4)
C5—C6—C7—N1	−179.5 (4)	S1'—C12—S1—C15	1.1 (3)
C10—C6—C7—C2	177.8 (4)	C13—C12—S1—C15	0.15 (17)
C5—C6—C7—C2	−1.0 (6)	C13'—C12—S1—C15	−155 (3)
C1—C2—C7—N1	65.3 (5)	C10—C12—S1'—C15'	175.7 (5)
C3—C2—C7—N1	−168.7 (4)	S1—C12—S1'—C15'	−4.1 (4)
C1—C2—C7—C6	−113.3 (5)	C13—C12—S1'—C15'	173.1 (11)
C3—C2—C7—C6	12.6 (6)	C13'—C12—S1'—C15'	0.42 (19)
C7—N1—C8—O1	179.8 (5)	C10—C12—C13—C14	178.9 (4)
C7—N1—C8—C9	0.7 (7)	S1'—C12—C13—C14	−3.2 (10)
O1—C8—C9—C10	−178.3 (5)	S1—C12—C13—C14	−0.1 (2)
N1—C8—C9—C10	0.8 (7)	C13'—C12—C13—C14	5.4 (5)
O1—C8—C9—C11	3.1 (7)	C10—C12—C13'—C14'	−175.7 (4)
N1—C8—C9—C11	−177.9 (4)	S1'—C12—C13'—C14'	0.2 (2)
C11—C9—C10—C6	176.3 (4)	S1—C12—C13'—C14'	25 (3)
C8—C9—C10—C6	−2.2 (6)	C13—C12—C13'—C14'	−2.5 (5)
C11—C9—C10—C12	−5.0 (6)	C12—C13—C14—C15	0.0 (4)
C8—C9—C10—C12	176.4 (4)	C12—C13'—C14'—C15'	−1.0 (5)
C7—C6—C10—C9	2.2 (5)	C13—C14—C15—S1	0.1 (6)
C5—C6—C10—C9	−179.1 (4)	C12—S1—C15—C14	−0.2 (4)
C7—C6—C10—C12	−176.4 (4)	C13'—C14'—C15'—S1'	1.3 (6)
C5—C6—C10—C12	2.3 (6)	C12—S1'—C15'—C14'	−1.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1i	0.88	1.94	2.801 (4)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O1i	0.88	1.94	2.801 (4)	168

Symmetry code: (i) .