5,6,7,8-Tetra-hydro-quinolin-8-one.

In the quinoline fused-ring system of the title compound, C(9)H(9)NO, the pyridine ring is planar to within 0.011 (3) Å, while the partially saturated cyclo-hexene ring adopts a sofa conformation with an asymmetry parameter ΔC(s)(C6) = 1.5 (4)°. There are no classical hydrogen bonds in the crystal structure. Mol-ecules form mol-ecular layers parallel to (100) with a distance between the layers of a/2 = 3.468 Å.

Related literature

The title compound is an inter­mediate for the synthesis of polyheterocycles giving photoluminescence (Kelly & Lebedev, 2002 ▶) and a key substrate to synthesis of its 8-amino substituted derivatives with pharmacological activity (e.g. Gudmundsson et al., 2009) ▶. For our ongoing study on the synthesis and structure of condensed pyridine and quinoline derivatives, see: Lipińska (2005 ▶); Karczmarzyk et al. (2010 ▶). For the synthesis, see: Kelly & Lebedev (2002 ▶). For a related structure, see: OXHYQU (Cygler et al., 1981 ▶). For structure inter­pretation tools, see: Bruno et al. (2002 ▶); Spek (2009 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For bond-length data, see: Allen et al. (1987 ▶). For asymmetry parameters, see: Duax & Norton (1975 ▶).

Experimental

Crystal data

C9H9NO

M = 147.17

Orthorhombic,

a = 6.9393 (2) Å

b = 8.0885 (3) Å

c = 13.4710 (4) Å

V = 756.11 (4) Å3

Z = 4

Cu Kα radiation

μ = 0.68 mm−1

T = 293 K

0.60 × 0.16 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.878, T max = 1.000

5358 measured reflections

761 independent reflections

734 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.153

S = 1.14

761 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016175/jh2281sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016175/jh2281Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016175/jh2281Isup3.cml

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

C9H9NO	Dx = 1.293 Mg m−3
Mr = 147.17	Melting point = 369–371 K
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 40 reflections
a = 6.9393 (2) Å	θ = 7.2–34.8°
b = 8.0885 (3) Å	µ = 0.68 mm−1
c = 13.4710 (4) Å	T = 293 K
V = 756.11 (4) Å3	Needle, colourless
Z = 4	0.60 × 0.16 × 0.15 mm
F(000) = 312

Bruker SMART APEXII CCD diffractometer	761 independent reflections
Radiation source: fine-focus sealed tube	734 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω scans	θmax = 65.0°, θmin = 6.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.878, Tmax = 1.000	k = −9→7
5358 measured reflections	l = −15→15

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) = 0.153	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.1138P)2 + 0.0433P] where P = (Fo2 + 2Fc2)/3
761 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.0077 (5)	0.3562 (2)	0.54598 (13)	0.0827 (8)
N1	0.0144 (4)	0.0574 (3)	0.64019 (14)	0.0617 (6)
C2	0.0232 (4)	−0.0911 (4)	0.68161 (18)	0.0673 (7)
H2	0.0116	−0.0986	0.7502	0.101*
C3	0.0486 (5)	−0.2350 (4)	0.6282 (2)	0.0763 (9)
H3	0.0575	−0.3364	0.6604	0.114*
C4	0.0606 (6)	−0.2257 (3)	0.5270 (2)	0.0784 (10)
H4	0.0776	−0.3212	0.4896	0.118*
C5	0.0569 (7)	−0.0575 (4)	0.36824 (19)	0.0850 (12)
H51	0.1908	−0.0533	0.3478	0.128*
H52	−0.0010	−0.1544	0.3381	0.128*
C6	−0.0431 (6)	0.0917 (4)	0.3321 (2)	0.0899 (11)
H61	−0.1807	0.0782	0.3419	0.135*
H62	−0.0203	0.1031	0.2613	0.135*
C7	0.0218 (5)	0.2459 (3)	0.38350 (19)	0.0685 (8)
H71	−0.0596	0.3370	0.3626	0.103*
H72	0.1526	0.2708	0.3630	0.103*
C8	0.0157 (4)	0.2338 (3)	0.49507 (19)	0.0547 (6)
C9	0.0250 (3)	0.0646 (3)	0.54022 (17)	0.0498 (6)
C10	0.0472 (4)	−0.0740 (3)	0.48064 (18)	0.0593 (7)

	U11	U22	U33	U12	U13	U23
O1	0.1330 (18)	0.0423 (10)	0.0727 (12)	−0.0004 (12)	0.0010 (14)	−0.0078 (7)
N1	0.0823 (14)	0.0571 (12)	0.0455 (10)	0.0067 (12)	0.0018 (10)	−0.0021 (8)
C2	0.0834 (17)	0.0693 (15)	0.0491 (12)	0.0051 (16)	0.0046 (12)	0.0103 (11)
C3	0.099 (2)	0.0553 (16)	0.0748 (16)	0.0030 (15)	0.0054 (16)	0.0198 (12)
C4	0.121 (3)	0.0434 (15)	0.0710 (17)	0.0049 (16)	0.0102 (17)	−0.0019 (11)
C5	0.146 (3)	0.0603 (17)	0.0493 (14)	−0.0020 (19)	0.0052 (16)	−0.0100 (11)
C6	0.141 (3)	0.080 (2)	0.0489 (13)	−0.011 (2)	−0.0132 (16)	0.0019 (13)
C7	0.0942 (18)	0.0564 (14)	0.0549 (13)	−0.0025 (14)	−0.0030 (14)	0.0134 (11)
C8	0.0668 (13)	0.0410 (12)	0.0563 (12)	−0.0016 (11)	0.0007 (12)	−0.0020 (9)
C9	0.0616 (12)	0.0445 (12)	0.0434 (10)	−0.0013 (11)	0.0012 (10)	−0.0015 (8)
C10	0.0805 (16)	0.0462 (13)	0.0512 (13)	−0.0051 (13)	0.0066 (11)	−0.0042 (10)

O1—C8	1.205 (3)	C5—H51	0.9700
N1—C2	1.326 (3)	C5—H52	0.9700
N1—C9	1.350 (3)	C6—C7	1.497 (4)
C2—C3	1.380 (4)	C6—H61	0.9700
C2—H2	0.9300	C6—H62	0.9700
C3—C4	1.368 (4)	C7—C8	1.507 (3)
C3—H3	0.9300	C7—H71	0.9700
C4—C10	1.380 (4)	C7—H72	0.9700
C4—H4	0.9300	C8—C9	1.499 (3)
C5—C6	1.475 (5)	C9—C10	1.387 (3)
C5—C10	1.521 (3)
C2—N1—C9	117.2 (2)	C5—C6—H62	109.0
N1—C2—C3	123.4 (2)	C7—C6—H62	109.0
N1—C2—H2	118.3	H61—C6—H62	107.8
C3—C2—H2	118.3	C6—C7—C8	113.5 (2)
C4—C3—C2	118.7 (2)	C6—C7—H71	108.9
C4—C3—H3	120.6	C8—C7—H71	108.9
C2—C3—H3	120.6	C6—C7—H72	108.9
C3—C4—C10	119.7 (2)	C8—C7—H72	108.9
C3—C4—H4	120.1	H71—C7—H72	107.7
C10—C4—H4	120.1	O1—C8—C9	121.4 (2)
C6—C5—C10	112.3 (3)	O1—C8—C7	121.0 (2)
C6—C5—H51	109.1	C9—C8—C7	117.57 (19)
C10—C5—H51	109.1	N1—C9—C10	123.3 (2)
C6—C5—H52	109.1	N1—C9—C8	116.21 (19)
C10—C5—H52	109.1	C10—C9—C8	120.5 (2)
H51—C5—H52	107.9	C4—C10—C9	117.7 (2)
C5—C6—C7	112.8 (3)	C4—C10—C5	121.7 (2)
C5—C6—H61	109.0	C9—C10—C5	120.7 (2)
C7—C6—H61	109.0
C9—N1—C2—C3	2.2 (4)	O1—C8—C9—C10	−175.6 (3)
N1—C2—C3—C4	−1.8 (5)	C7—C8—C9—C10	2.9 (4)
C2—C3—C4—C10	0.1 (6)	C3—C4—C10—C9	1.0 (5)
C10—C5—C6—C7	52.3 (4)	C3—C4—C10—C5	−179.1 (4)
C5—C6—C7—C8	−51.6 (4)	N1—C9—C10—C4	−0.5 (4)
C6—C7—C8—O1	−158.0 (3)	C8—C9—C10—C4	178.1 (3)
C6—C7—C8—C9	23.5 (4)	N1—C9—C10—C5	179.6 (3)
C2—N1—C9—C10	−1.0 (4)	C8—C9—C10—C5	−1.8 (4)
C2—N1—C9—C8	−179.7 (2)	C6—C5—C10—C4	154.3 (3)
O1—C8—C9—N1	3.1 (4)	C6—C5—C10—C9	−25.9 (5)
C7—C8—C9—N1	−178.4 (3)