Crystal structure of cis-1-(2-methyl-1,2,3,4-tetra-hydro-quinolin-4-yl)azepan-2-one.

In the title compound, C16H22N2O, the azepan-2-one ring adopts a chair conformation, while the 1,2,3,4-tetra-hydro-pyridine ring adopts a half-chair conformation. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming supra-molecular chains propagated along [10-1], with weak C-H⋯O inter-actions occurring between the chains.

Related literature

For applications of tetra­hydro­quinolines, see: Konishi et al. (1990 ▶).

Experimental

Crystal data

C16H22N2O

M = 258.36

Monoclinic,

a = 9.1640 (17) Å

b = 13.1687 (18) Å

c = 11.988 (2) Å

β = 96.825 (11)°

V = 1436.4 (4) Å3

Z = 4

Cu Kα radiation

μ = 0.59 mm−1

T = 296 K

0.23 × 0.22 × 0.21 mm

Data collection

Bruker X8 Proteum diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.874, T max = 0.884

7903 measured reflections

2343 independent reflections

2106 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.139

S = 1.06

2343 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: Mercury.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814017826/xu5808sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814017826/xu5808Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814017826/xu5808Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814017826/xu5808fig1.tif

A view of the title mol­ecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

a . DOI: 10.1107/S1600536814017826/xu5808fig2.tif

A viewed along the a axis of the crystal packing of the title compound.

CCDC reference: 1017682

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

C16H22N2O	F(000) = 560
Mr = 258.36	Dx = 1.195 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 2343 reflections
a = 9.1640 (17) Å	θ = 6.7–64.8°
b = 13.1687 (18) Å	µ = 0.59 mm−1
c = 11.988 (2) Å	T = 296 K
β = 96.825 (11)°	Block, colorless
V = 1436.4 (4) Å3	0.23 × 0.22 × 0.21 mm
Z = 4

Bruker X8 Proteum diffractometer	2343 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	2106 reflections with I > 2σ(I)
Helios multilayer optics monochromator	Rint = 0.028
Detector resolution: 18.4 pixels mm-1	θmax = 64.8°, θmin = 6.7°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −15→4
Tmin = 0.874, Tmax = 0.884	l = −14→13
7903 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0671P)2 + 0.4283P] where P = (Fo2 + 2Fc2)/3
2343 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O19	0.20029 (15)	0.75502 (10)	0.32245 (11)	0.0661 (5)
N1	0.53573 (16)	0.85016 (11)	−0.01036 (12)	0.0538 (5)
N12	0.28345 (14)	0.90157 (10)	0.25474 (10)	0.0438 (4)
C2	0.60480 (18)	0.82217 (14)	0.10008 (15)	0.0511 (6)
C3	0.52791 (17)	0.87701 (14)	0.18769 (14)	0.0497 (5)
C4	0.36664 (17)	0.84597 (12)	0.17675 (13)	0.0421 (5)
C5	0.29631 (17)	0.85491 (12)	0.05626 (13)	0.0439 (5)
C6	0.1450 (2)	0.86076 (16)	0.03030 (16)	0.0593 (6)
C7	0.0790 (2)	0.86425 (19)	−0.07861 (17)	0.0718 (8)
C8	0.1649 (3)	0.86264 (17)	−0.16454 (16)	0.0700 (7)
C9	0.3153 (2)	0.85678 (14)	−0.14226 (15)	0.0605 (7)
C10	0.38380 (19)	0.85289 (12)	−0.03180 (14)	0.0459 (5)
C11	0.7676 (2)	0.84612 (19)	0.1097 (2)	0.0743 (8)
C13	0.28372 (19)	1.01269 (13)	0.25122 (14)	0.0514 (6)
C14	0.3621 (2)	1.06237 (15)	0.35552 (17)	0.0640 (7)
C15	0.2718 (3)	1.06735 (17)	0.45383 (18)	0.0770 (8)
C16	0.2169 (3)	0.96542 (17)	0.49058 (17)	0.0720 (8)
C17	0.1190 (2)	0.90829 (16)	0.40028 (17)	0.0627 (7)
C18	0.20364 (18)	0.84820 (14)	0.32180 (13)	0.0486 (6)
H1	0.58880	0.86510	−0.06260	0.0640*
H2	0.59290	0.74890	0.10990	0.0610*
H3A	0.53550	0.94980	0.17750	0.0600*
H3B	0.57490	0.86010	0.26220	0.0600*
H4	0.36380	0.77400	0.19710	0.0510*
H6	0.08640	0.86240	0.08850	0.0710*
H7	−0.02280	0.86770	−0.09380	0.0860*
H8	0.12120	0.86550	−0.23860	0.0840*
H9	0.37220	0.85540	−0.20150	0.0730*
H11A	0.81160	0.80920	0.05330	0.1120*
H11B	0.81330	0.82670	0.18280	0.1120*
H11C	0.78080	0.91760	0.09920	0.1120*
H13A	0.18280	1.03640	0.24060	0.0620*
H13B	0.33020	1.03440	0.18670	0.0620*
H14A	0.38960	1.13080	0.33670	0.0770*
H14B	0.45190	1.02500	0.37870	0.0770*
H15A	0.33110	1.09830	0.51720	0.0920*
H15B	0.18770	1.11120	0.43340	0.0920*
H16A	0.16270	0.97610	0.55430	0.0860*
H16B	0.30120	0.92320	0.51580	0.0860*
H17A	0.05640	0.86230	0.43620	0.0750*
H17B	0.05600	0.95660	0.35650	0.0750*

	U11	U22	U33	U12	U13	U23
O19	0.0806 (9)	0.0577 (9)	0.0692 (9)	−0.0120 (7)	0.0477 (7)	−0.0006 (6)
N1	0.0525 (8)	0.0624 (9)	0.0526 (8)	0.0030 (7)	0.0321 (7)	0.0032 (7)
N12	0.0447 (7)	0.0501 (8)	0.0406 (7)	0.0023 (6)	0.0221 (6)	0.0023 (6)
C2	0.0446 (9)	0.0534 (10)	0.0599 (10)	0.0014 (7)	0.0254 (8)	0.0009 (8)
C3	0.0411 (8)	0.0607 (10)	0.0501 (9)	−0.0022 (7)	0.0173 (7)	−0.0045 (8)
C4	0.0419 (8)	0.0472 (9)	0.0412 (8)	−0.0003 (7)	0.0212 (6)	0.0003 (7)
C5	0.0441 (9)	0.0469 (9)	0.0436 (9)	−0.0039 (7)	0.0179 (7)	−0.0008 (7)
C6	0.0468 (10)	0.0805 (13)	0.0529 (10)	−0.0060 (9)	0.0161 (8)	0.0002 (9)
C7	0.0567 (11)	0.0964 (16)	0.0609 (12)	−0.0073 (11)	0.0017 (9)	0.0001 (11)
C8	0.0819 (14)	0.0791 (14)	0.0470 (10)	−0.0082 (11)	0.0000 (10)	−0.0047 (9)
C9	0.0812 (14)	0.0618 (11)	0.0424 (9)	−0.0068 (9)	0.0238 (9)	−0.0057 (8)
C10	0.0555 (9)	0.0415 (9)	0.0448 (9)	−0.0023 (7)	0.0227 (7)	−0.0012 (7)
C11	0.0451 (10)	0.0932 (16)	0.0900 (15)	0.0016 (10)	0.0301 (10)	−0.0044 (12)
C13	0.0576 (10)	0.0523 (10)	0.0480 (9)	0.0097 (8)	0.0219 (8)	0.0091 (7)
C14	0.0803 (13)	0.0496 (11)	0.0641 (12)	0.0029 (9)	0.0170 (10)	−0.0019 (9)
C15	0.1127 (18)	0.0636 (13)	0.0579 (12)	0.0138 (12)	0.0233 (12)	−0.0091 (10)
C16	0.0985 (16)	0.0738 (14)	0.0498 (11)	0.0185 (12)	0.0348 (10)	−0.0001 (9)
C17	0.0607 (11)	0.0735 (13)	0.0616 (11)	0.0111 (9)	0.0388 (9)	0.0080 (10)
C18	0.0454 (9)	0.0591 (11)	0.0454 (9)	0.0002 (7)	0.0225 (7)	0.0031 (7)

O19—C18	1.228 (2)	C2—H2	0.9800
N1—C2	1.446 (2)	C3—H3A	0.9700
N1—C10	1.386 (2)	C3—H3B	0.9700
N12—C4	1.470 (2)	C4—H4	0.9800
N12—C13	1.464 (2)	C6—H6	0.9300
N12—C18	1.347 (2)	C7—H7	0.9300
N1—H1	0.8600	C8—H8	0.9300
C2—C11	1.516 (3)	C9—H9	0.9300
C2—C3	1.516 (2)	C11—H11A	0.9600
C3—C4	1.524 (2)	C11—H11B	0.9600
C4—C5	1.515 (2)	C11—H11C	0.9600
C5—C6	1.387 (2)	C13—H13A	0.9700
C5—C10	1.400 (2)	C13—H13B	0.9700
C6—C7	1.373 (3)	C14—H14A	0.9700
C7—C8	1.369 (3)	C14—H14B	0.9700
C8—C9	1.375 (3)	C15—H15A	0.9700
C9—C10	1.397 (2)	C15—H15B	0.9700
C13—C14	1.515 (3)	C16—H16A	0.9700
C14—C15	1.520 (3)	C16—H16B	0.9700
C15—C16	1.517 (3)	C17—H17A	0.9700
C16—C17	1.521 (3)	C17—H17B	0.9700
C17—C18	1.512 (3)
C2—N1—C10	119.82 (14)	C5—C4—H4	107.00
C4—N12—C13	118.48 (12)	C5—C6—H6	119.00
C4—N12—C18	118.62 (13)	C7—C6—H6	119.00
C13—N12—C18	122.79 (14)	C6—C7—H7	120.00
C2—N1—H1	120.00	C8—C7—H7	120.00
C10—N1—H1	120.00	C7—C8—H8	120.00
C3—C2—C11	112.49 (16)	C9—C8—H8	120.00
N1—C2—C3	108.91 (14)	C8—C9—H9	120.00
N1—C2—C11	109.66 (16)	C10—C9—H9	120.00
C2—C3—C4	109.79 (14)	C2—C11—H11A	109.00
N12—C4—C5	111.95 (13)	C2—C11—H11B	109.00
C3—C4—C5	111.08 (13)	C2—C11—H11C	109.00
N12—C4—C3	112.50 (13)	H11A—C11—H11B	110.00
C6—C5—C10	118.62 (15)	H11A—C11—H11C	110.00
C4—C5—C6	121.27 (15)	H11B—C11—H11C	109.00
C4—C5—C10	120.05 (14)	N12—C13—H13A	109.00
C5—C6—C7	122.08 (17)	N12—C13—H13B	109.00
C6—C7—C8	119.17 (19)	C14—C13—H13A	109.00
C7—C8—C9	120.51 (18)	C14—C13—H13B	109.00
C8—C9—C10	120.89 (17)	H13A—C13—H13B	108.00
N1—C10—C5	120.90 (15)	C13—C14—H14A	109.00
N1—C10—C9	120.33 (16)	C13—C14—H14B	109.00
C5—C10—C9	118.75 (16)	C15—C14—H14A	109.00
N12—C13—C14	114.22 (14)	C15—C14—H14B	109.00
C13—C14—C15	114.23 (16)	H14A—C14—H14B	108.00
C14—C15—C16	114.64 (18)	C14—C15—H15A	109.00
C15—C16—C17	114.77 (18)	C14—C15—H15B	109.00
C16—C17—C18	113.52 (17)	C16—C15—H15A	109.00
N12—C18—C17	116.96 (16)	C16—C15—H15B	109.00
O19—C18—N12	122.76 (16)	H15A—C15—H15B	108.00
O19—C18—C17	120.27 (16)	C15—C16—H16A	109.00
N1—C2—H2	109.00	C15—C16—H16B	109.00
C3—C2—H2	109.00	C17—C16—H16A	109.00
C11—C2—H2	109.00	C17—C16—H16B	109.00
C2—C3—H3A	110.00	H16A—C16—H16B	108.00
C2—C3—H3B	110.00	C16—C17—H17A	109.00
C4—C3—H3A	110.00	C16—C17—H17B	109.00
C4—C3—H3B	110.00	C18—C17—H17A	109.00
H3A—C3—H3B	108.00	C18—C17—H17B	109.00
N12—C4—H4	107.00	H17A—C17—H17B	108.00
C3—C4—H4	107.00
C10—N1—C2—C3	−44.6 (2)	C3—C4—C5—C6	−160.41 (16)
C10—N1—C2—C11	−168.08 (16)	C3—C4—C5—C10	22.4 (2)
C2—N1—C10—C5	16.6 (2)	C4—C5—C6—C7	−176.99 (19)
C2—N1—C10—C9	−165.36 (16)	C10—C5—C6—C7	0.2 (3)
C13—N12—C4—C3	56.10 (18)	C4—C5—C10—N1	−4.7 (2)
C13—N12—C4—C5	−69.81 (17)	C4—C5—C10—C9	177.21 (15)
C18—N12—C4—C3	−127.62 (15)	C6—C5—C10—N1	178.05 (16)
C18—N12—C4—C5	106.48 (16)	C6—C5—C10—C9	0.0 (2)
C4—N12—C13—C14	−113.04 (16)	C5—C6—C7—C8	−0.5 (3)
C18—N12—C13—C14	70.8 (2)	C6—C7—C8—C9	0.5 (3)
C4—N12—C18—O19	1.8 (2)	C7—C8—C9—C10	−0.3 (3)
C4—N12—C18—C17	−179.65 (14)	C8—C9—C10—N1	−178.00 (17)
C13—N12—C18—O19	177.93 (15)	C8—C9—C10—C5	0.1 (3)
C13—N12—C18—C17	−3.5 (2)	N12—C13—C14—C15	−79.6 (2)
N1—C2—C3—C4	60.77 (18)	C13—C14—C15—C16	56.7 (3)
C11—C2—C3—C4	−177.44 (16)	C14—C15—C16—C17	−59.5 (3)
C2—C3—C4—N12	−176.30 (13)	C15—C16—C17—C18	83.3 (2)
C2—C3—C4—C5	−49.92 (18)	C16—C17—C18—O19	112.4 (2)
N12—C4—C5—C6	−33.7 (2)	C16—C17—C18—N12	−66.2 (2)
N12—C4—C5—C10	149.10 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O19i	0.86	2.40	2.988 (2)	126
C14—H14A···O19ii	0.97	2.57	3.320 (2)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O19i	0.86	2.40	2.988 (2)	126
C14—H14A⋯O19ii	0.97	2.57	3.320 (2)	134

Symmetry codes: (i) ; (ii) .