1-Methyl-3-(3-oxocyclo-hex-1-en-yl)azepan-2-one.

The title compound, C(13)H(19)NO(2), is a inter-mediate in the synthesis of the opioid analgesic meptazinol. In the crystal structure, a weak inter-molecular C-H⋯O inter-action occurs.

Related literature

For related literature, see: Bradley et al. (1980 ▶); Hoskin & Hanks (1991 ▶).

Experimental

Crystal data

C13H19NO2

M = 221.29

Monoclinic,

a = 9.450 (4) Å

b = 10.665 (3) Å

c = 11.963 (4) Å

β = 95.33 (3)°

V = 1200.5 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 294 (2) K

0.46 × 0.44 × 0.40 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

2361 measured reflections

2198 independent reflections

1235 reflections with I > 2σ(I)

R int = 0.005

3 standard reflections every 150 reflections intensity decay: 0.7%

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.163

S = 1.06

2198 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.25 e Å−3

Data collection: DIFRAC (Gabe & White, 1993 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802895X/hb2790sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802895X/hb2790Isup2.hkl

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

C13H19NO2	F(000) = 480
Mr = 221.29	Dx = 1.224 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 20 reflections
a = 9.450 (4) Å	θ = 4.2–7.3°
b = 10.665 (3) Å	µ = 0.08 mm−1
c = 11.963 (4) Å	T = 294 K
β = 95.33 (3)°	Block, colourless
V = 1200.5 (7) Å3	0.46 × 0.44 × 0.40 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.005
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 2.2°
graphite	h = −11→11
ω/2θ scans	k = 0→12
2361 measured reflections	l = −4→14
2198 independent reflections	3 standard reflections every 150 reflections
1235 reflections with I > 2σ(I)	intensity decay: 0.7%

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0788P)2 + 0.1025P] where P = (Fo2 + 2Fc2)/3
2198 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.25 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
O1	0.95711 (19)	0.09365 (17)	0.84861 (15)	0.0577 (5)
O2	0.5608 (2)	0.4437 (2)	0.8362 (2)	0.0810 (7)
N1	0.8874 (2)	−0.0883 (2)	0.76476 (17)	0.0513 (6)
C1	0.8668 (3)	0.0106 (2)	0.83106 (19)	0.0419 (6)
C2	0.7256 (2)	0.0187 (2)	0.88309 (18)	0.0426 (6)
H2	0.6495	0.0047	0.8230	0.051*
C3	0.7118 (3)	−0.0828 (2)	0.9732 (2)	0.0539 (7)
H3A	0.8030	−0.0930	1.0165	0.065*
H3B	0.6442	−0.0546	1.0240	0.065*
C4	0.6637 (3)	−0.2092 (3)	0.9246 (2)	0.0638 (8)
H4A	0.6529	−0.2664	0.9862	0.077*
H4B	0.5709	−0.1989	0.8837	0.077*
C5	0.7628 (3)	−0.2687 (3)	0.8468 (2)	0.0659 (8)
H5A	0.8541	−0.2834	0.8887	0.079*
H5B	0.7243	−0.3495	0.8224	0.079*
C6	0.7860 (3)	−0.1915 (3)	0.7444 (2)	0.0608 (8)
H6A	0.8194	−0.2463	0.6877	0.073*
H6B	0.6954	−0.1571	0.7142	0.073*
C7	1.0154 (3)	−0.0913 (3)	0.7053 (2)	0.0669 (9)
H7A	0.9931	−0.0626	0.6297	0.100*
H7B	1.0509	−0.1756	0.7043	0.100*
H7C	1.0863	−0.0377	0.7428	0.100*
C8	0.7091 (2)	0.1503 (2)	0.9263 (2)	0.0435 (6)
C9	0.6343 (3)	0.2358 (2)	0.8651 (2)	0.0477 (7)
H9	0.5871	0.2107	0.7971	0.057*
C10	0.6223 (3)	0.3659 (3)	0.8985 (2)	0.0553 (7)
C11	0.6880 (3)	0.4006 (3)	1.0140 (3)	0.0702 (9)
H11A	0.7247	0.4854	1.0115	0.084*
H11B	0.6142	0.4004	1.0652	0.084*
C12	0.8034 (4)	0.3173 (3)	1.0592 (3)	0.0766 (10)
H12A	0.8193	0.3316	1.1395	0.092*
H12B	0.8895	0.3418	1.0266	0.092*
C13	0.7821 (3)	0.1819 (3)	1.0404 (2)	0.0631 (8)
H13A	0.7258	0.1490	1.0975	0.076*
H13B	0.8738	0.1404	1.0490	0.076*

	U11	U22	U33	U12	U13	U23
O1	0.0533 (11)	0.0494 (12)	0.0708 (12)	−0.0065 (9)	0.0074 (9)	−0.0010 (9)
O2	0.0766 (15)	0.0520 (14)	0.1098 (18)	0.0121 (11)	−0.0160 (13)	0.0039 (12)
N1	0.0595 (14)	0.0449 (14)	0.0509 (12)	0.0038 (11)	0.0122 (10)	−0.0052 (11)
C1	0.0468 (14)	0.0371 (14)	0.0404 (13)	0.0028 (12)	−0.0037 (11)	0.0059 (12)
C2	0.0436 (14)	0.0423 (16)	0.0398 (12)	0.0036 (11)	−0.0066 (10)	−0.0034 (12)
C3	0.0548 (16)	0.0517 (18)	0.0549 (16)	−0.0035 (13)	0.0043 (13)	0.0060 (13)
C4	0.0605 (17)	0.0525 (18)	0.0776 (19)	−0.0097 (15)	0.0017 (15)	0.0109 (16)
C5	0.0652 (18)	0.0398 (16)	0.091 (2)	−0.0055 (14)	−0.0008 (17)	−0.0046 (16)
C6	0.0668 (18)	0.0487 (17)	0.0656 (17)	0.0024 (14)	−0.0002 (14)	−0.0200 (15)
C7	0.080 (2)	0.061 (2)	0.0636 (17)	0.0157 (16)	0.0262 (16)	0.0046 (15)
C8	0.0421 (13)	0.0441 (16)	0.0440 (13)	0.0013 (12)	0.0018 (11)	−0.0048 (12)
C9	0.0455 (14)	0.0474 (16)	0.0487 (14)	0.0036 (13)	−0.0042 (11)	−0.0061 (13)
C10	0.0407 (14)	0.0518 (18)	0.0734 (19)	0.0042 (14)	0.0057 (13)	−0.0026 (16)
C11	0.075 (2)	0.0511 (19)	0.084 (2)	0.0028 (16)	0.0042 (17)	−0.0231 (17)
C12	0.097 (3)	0.067 (2)	0.0618 (19)	−0.0014 (19)	−0.0136 (17)	−0.0134 (17)
C13	0.0736 (19)	0.062 (2)	0.0505 (16)	0.0072 (16)	−0.0119 (14)	−0.0152 (14)

O1—C1	1.234 (3)	C6—H6A	0.9700
O2—C10	1.225 (3)	C6—H6B	0.9700
N1—C1	1.344 (3)	C7—H7A	0.9600
N1—C7	1.459 (3)	C7—H7B	0.9600
N1—C6	1.465 (3)	C7—H7C	0.9600
C1—C2	1.527 (3)	C8—C9	1.330 (3)
C2—C8	1.509 (3)	C8—C13	1.509 (3)
C2—C3	1.542 (3)	C9—C10	1.452 (4)
C2—H2	0.9800	C9—H9	0.9300
C3—C4	1.520 (4)	C10—C11	1.507 (4)
C3—H3A	0.9700	C11—C12	1.470 (4)
C3—H3B	0.9700	C11—H11A	0.9700
C4—C5	1.520 (4)	C11—H11B	0.9700
C4—H4A	0.9700	C12—C13	1.473 (4)
C4—H4B	0.9700	C12—H12A	0.9700
C5—C6	1.509 (4)	C12—H12B	0.9700
C5—H5A	0.9700	C13—H13A	0.9700
C5—H5B	0.9700	C13—H13B	0.9700
C1—N1—C7	118.5 (2)	H6A—C6—H6B	107.6
C1—N1—C6	124.0 (2)	N1—C7—H7A	109.5
C7—N1—C6	117.5 (2)	N1—C7—H7B	109.5
O1—C1—N1	121.8 (2)	H7A—C7—H7B	109.5
O1—C1—C2	120.4 (2)	N1—C7—H7C	109.5
N1—C1—C2	117.7 (2)	H7A—C7—H7C	109.5
C8—C2—C1	108.3 (2)	H7B—C7—H7C	109.5
C8—C2—C3	113.3 (2)	C9—C8—C2	121.0 (2)
C1—C2—C3	112.3 (2)	C9—C8—C13	121.3 (2)
C8—C2—H2	107.6	C2—C8—C13	117.6 (2)
C1—C2—H2	107.6	C8—C9—C10	123.7 (2)
C3—C2—H2	107.6	C8—C9—H9	118.1
C4—C3—C2	113.4 (2)	C10—C9—H9	118.1
C4—C3—H3A	108.9	O2—C10—C9	121.7 (3)
C2—C3—H3A	108.9	O2—C10—C11	121.5 (3)
C4—C3—H3B	108.9	C9—C10—C11	116.8 (2)
C2—C3—H3B	108.9	C12—C11—C10	114.6 (2)
H3A—C3—H3B	107.7	C12—C11—H11A	108.6
C5—C4—C3	115.1 (2)	C10—C11—H11A	108.6
C5—C4—H4A	108.5	C12—C11—H11B	108.6
C3—C4—H4A	108.5	C10—C11—H11B	108.6
C5—C4—H4B	108.5	H11A—C11—H11B	107.6
C3—C4—H4B	108.5	C11—C12—C13	116.7 (3)
H4A—C4—H4B	107.5	C11—C12—H12A	108.1
C6—C5—C4	114.4 (2)	C13—C12—H12A	108.1
C6—C5—H5A	108.7	C11—C12—H12B	108.1
C4—C5—H5A	108.7	C13—C12—H12B	108.1
C6—C5—H5B	108.7	H12A—C12—H12B	107.3
C4—C5—H5B	108.7	C12—C13—C8	113.6 (2)
H5A—C5—H5B	107.6	C12—C13—H13A	108.8
N1—C6—C5	114.6 (2)	C8—C13—H13A	108.8
N1—C6—H6A	108.6	C12—C13—H13B	108.8
C5—C6—H6A	108.6	C8—C13—H13B	108.8
N1—C6—H6B	108.6	H13A—C13—H13B	107.7
C5—C6—H6B	108.6
C7—N1—C1—O1	−5.0 (3)	C1—C2—C8—C9	96.5 (3)
C6—N1—C1—O1	177.8 (2)	C3—C2—C8—C9	−138.2 (2)
C7—N1—C1—C2	173.9 (2)	C1—C2—C8—C13	−82.6 (3)
C6—N1—C1—C2	−3.4 (3)	C3—C2—C8—C13	42.6 (3)
O1—C1—C2—C8	14.2 (3)	C2—C8—C9—C10	−175.7 (2)
N1—C1—C2—C8	−164.7 (2)	C13—C8—C9—C10	3.4 (4)
O1—C1—C2—C3	−111.7 (3)	C8—C9—C10—O2	174.7 (3)
N1—C1—C2—C3	69.4 (3)	C8—C9—C10—C11	−5.8 (4)
C8—C2—C3—C4	154.6 (2)	O2—C10—C11—C12	−156.1 (3)
C1—C2—C3—C4	−82.2 (3)	C9—C10—C11—C12	24.4 (4)
C2—C3—C4—C5	61.1 (3)	C10—C11—C12—C13	−41.6 (4)
C3—C4—C5—C6	−60.1 (3)	C11—C12—C13—C8	38.6 (4)
C1—N1—C6—C5	−64.5 (3)	C9—C8—C13—C12	−19.4 (4)
C7—N1—C6—C5	118.2 (3)	C2—C8—C13—C12	159.8 (3)
C4—C5—C6—N1	79.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O1i	0.96	2.54	3.436 (4)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯O1i	0.96	2.54	3.436 (4)	155

Symmetry code: (i) .