N-(2-Oxo-2,3,4,5,6,7-hexa-hydro-1H-azepin-3-yl)cyclo-hexa-necarboxamide.

In the title compound, C13H22N2O2, both the six-membered ring and the seven-membered lactam ring adopt chair conformations. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds between inversion-related lactam rings into centrosymmetric dimers with an R 2 (2)(8) graph-set motif. Further N-H⋯O hydrogen bonds link the molecules into [100] chains.

Related literature

For background information on 3-(acyl­amino)­azepan-2-ones, see: Fox et al. (2009 ▶); Grainger & Fox (2006 ▶). For a related crystal structure, see: Zhu et al. (2007 ▶).

Experimental

Crystal data

C13H22N2O2

M = 238.33

Triclinic,

a = 5.007 (1) Å

b = 11.642 (2) Å

c = 12.739 (3) Å

α = 63.66 (3)°

β = 82.69 (3)°

γ = 82.75 (3)°

V = 658.0 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.976, T max = 0.992

2700 measured reflections

2400 independent reflections

1581 reflections with I > 2σ(I)

R int = 0.073

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.177

S = 1.01

2400 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) Y, I. DOI: 10.1107/S1600536813031863/pk2501sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031863/pk2501Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813031863/pk2501Isup3.cml

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

C13H22N2O2	Z = 2
Mr = 238.33	F(000) = 260
Triclinic, P1	Dx = 1.203 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.007 (1) Å	Cell parameters from 25 reflections
b = 11.642 (2) Å	θ = 9–13°
c = 12.739 (3) Å	µ = 0.08 mm−1
α = 63.66 (3)°	T = 293 K
β = 82.69 (3)°	Block, colorless
γ = 82.75 (3)°	0.30 × 0.20 × 0.10 mm
V = 658.0 (2) Å3

Enraf–Nonius CAD-4 diffractometer	1581 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.073
Graphite monochromator	θmax = 25.4°, θmin = 1.8°
ω/2θ scans	h = 0→6
Absorption correction: ψ scan (North et al., 1968)	k = −13→14
Tmin = 0.976, Tmax = 0.992	l = −15→15
2700 measured reflections	3 standard reflections every 200 reflections
2400 independent reflections	intensity decay: 1%

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.095P)2] where P = (Fo2 + 2Fc2)/3
2400 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.21 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
N1	0.3592 (4)	0.2916 (2)	0.81058 (18)	0.0438 (6)
H1A	0.5252	0.3096	0.7936	0.053*
O1	−0.0132 (4)	0.2579 (2)	0.74942 (18)	0.0665 (7)
C1	0.4450 (6)	0.1452 (3)	0.6317 (3)	0.0548 (8)
H1B	0.5415	0.0899	0.7003	0.066*
H1C	0.2722	0.1110	0.6407	0.066*
O2	0.5524 (4)	0.42401 (18)	0.90229 (15)	0.0477 (5)
N2	0.2504 (4)	0.3723 (2)	1.05959 (17)	0.0430 (6)
H2A	0.3272	0.4210	1.0794	0.052*
C2	0.6071 (7)	0.1457 (3)	0.5219 (3)	0.0714 (10)
H2B	0.7850	0.1738	0.5161	0.086*
H2C	0.6295	0.0592	0.5276	0.086*
C3	0.4643 (7)	0.2349 (4)	0.4128 (3)	0.0727 (11)
H3A	0.5718	0.2357	0.3436	0.087*
H3B	0.2912	0.2037	0.4163	0.087*
C4	0.4213 (8)	0.3700 (3)	0.4037 (3)	0.0719 (10)
H4A	0.5951	0.4040	0.3930	0.086*
H4B	0.3228	0.4249	0.3357	0.086*
C5	0.2662 (6)	0.3715 (3)	0.5124 (2)	0.0508 (7)
H5A	0.0850	0.3471	0.5176	0.061*
H5B	0.2512	0.4582	0.5060	0.061*
C6	0.3986 (5)	0.2813 (2)	0.6235 (2)	0.0376 (6)
H6A	0.5742	0.3117	0.6210	0.045*
C7	0.2294 (5)	0.2772 (2)	0.7325 (2)	0.0408 (6)
C8	0.2270 (5)	0.2776 (2)	0.9237 (2)	0.0382 (6)
H8A	0.0359	0.3077	0.9136	0.046*
C9	0.3562 (5)	0.3637 (2)	0.9613 (2)	0.0353 (6)
C10	0.0196 (5)	0.3088 (3)	1.1375 (2)	0.0468 (7)
H10A	−0.1360	0.3313	1.0919	0.056*
H10B	−0.0225	0.3411	1.1964	0.056*
C11	0.0673 (7)	0.1631 (3)	1.1989 (2)	0.0549 (8)
H11A	0.2469	0.1405	1.2267	0.066*
H11B	−0.0617	0.1301	1.2670	0.066*
C12	0.0410 (6)	0.0989 (3)	1.1204 (2)	0.0534 (8)
H12A	−0.1396	0.1209	1.0937	0.064*
H12B	0.0611	0.0064	1.1667	0.064*
C13	0.2449 (6)	0.1356 (3)	1.0132 (2)	0.0479 (7)
H13A	0.2224	0.0839	0.9731	0.057*
H13B	0.4250	0.1130	1.0404	0.057*

	U11	U22	U33	U12	U13	U23
N1	0.0397 (12)	0.0635 (15)	0.0449 (12)	−0.0215 (10)	0.0136 (10)	−0.0387 (11)
O1	0.0423 (12)	0.1187 (19)	0.0656 (14)	−0.0274 (11)	0.0159 (10)	−0.0641 (14)
C1	0.0622 (18)	0.0482 (17)	0.0599 (18)	−0.0033 (14)	0.0042 (15)	−0.0314 (15)
O2	0.0554 (11)	0.0538 (11)	0.0469 (10)	−0.0262 (9)	0.0179 (9)	−0.0336 (9)
N2	0.0517 (13)	0.0472 (13)	0.0420 (12)	−0.0192 (10)	0.0138 (10)	−0.0306 (10)
C2	0.068 (2)	0.079 (2)	0.099 (3)	−0.0141 (18)	0.022 (2)	−0.071 (2)
C3	0.073 (2)	0.111 (3)	0.062 (2)	−0.033 (2)	0.0272 (18)	−0.065 (2)
C4	0.094 (3)	0.077 (2)	0.0431 (17)	−0.029 (2)	0.0159 (17)	−0.0247 (16)
C5	0.0596 (18)	0.0468 (16)	0.0490 (16)	−0.0079 (13)	0.0016 (14)	−0.0242 (13)
C6	0.0378 (13)	0.0428 (14)	0.0415 (14)	−0.0134 (11)	0.0080 (11)	−0.0270 (12)
C7	0.0373 (14)	0.0506 (16)	0.0474 (15)	−0.0141 (11)	0.0088 (12)	−0.0332 (13)
C8	0.0371 (13)	0.0455 (15)	0.0413 (14)	−0.0134 (11)	0.0101 (11)	−0.0281 (12)
C9	0.0370 (13)	0.0357 (13)	0.0369 (13)	−0.0098 (11)	0.0065 (11)	−0.0199 (11)
C10	0.0506 (16)	0.0488 (16)	0.0448 (15)	−0.0134 (12)	0.0154 (13)	−0.0263 (13)
C11	0.0694 (19)	0.0503 (17)	0.0468 (16)	−0.0218 (14)	0.0153 (15)	−0.0236 (14)
C12	0.0667 (18)	0.0439 (16)	0.0517 (17)	−0.0234 (14)	0.0096 (15)	−0.0215 (13)
C13	0.0565 (16)	0.0448 (16)	0.0565 (17)	−0.0137 (13)	0.0070 (14)	−0.0351 (14)

N1—C7	1.334 (3)	C4—H4B	0.9700
N1—C8	1.455 (3)	C5—C6	1.513 (4)
N1—H1A	0.8600	C5—H5A	0.9700
O1—C7	1.238 (3)	C5—H5B	0.9700
C1—C2	1.523 (4)	C6—C7	1.516 (3)
C1—C6	1.530 (3)	C6—H6A	0.9800
C1—H1B	0.9700	C8—C9	1.524 (3)
C1—H1C	0.9700	C8—C13	1.536 (4)
O2—C9	1.241 (3)	C8—H8A	0.9800
N2—C9	1.337 (3)	C10—C11	1.522 (4)
N2—C10	1.462 (3)	C10—H10A	0.9700
N2—H2A	0.8600	C10—H10B	0.9700
C2—C3	1.519 (5)	C11—C12	1.516 (4)
C2—H2B	0.9700	C11—H11A	0.9700
C2—H2C	0.9700	C11—H11B	0.9700
C3—C4	1.515 (5)	C12—C13	1.526 (4)
C3—H3A	0.9700	C12—H12A	0.9700
C3—H3B	0.9700	C12—H12B	0.9700
C4—C5	1.505 (4)	C13—H13A	0.9700
C4—H4A	0.9700	C13—H13B	0.9700
C7—N1—C8	121.7 (2)	C5—C6—H6A	108.5
C7—N1—H1A	119.2	C7—C6—H6A	108.5
C8—N1—H1A	119.2	C1—C6—H6A	108.5
C2—C1—C6	110.7 (2)	O1—C7—N1	122.0 (2)
C2—C1—H1B	109.5	O1—C7—C6	121.9 (2)
C6—C1—H1B	109.5	N1—C7—C6	116.1 (2)
C2—C1—H1C	109.5	N1—C8—C9	108.04 (19)
C6—C1—H1C	109.5	N1—C8—C13	110.16 (19)
H1B—C1—H1C	108.1	C9—C8—C13	113.2 (2)
C9—N2—C10	127.8 (2)	N1—C8—H8A	108.5
C9—N2—H2A	116.1	C9—C8—H8A	108.5
C10—N2—H2A	116.1	C13—C8—H8A	108.5
C3—C2—C1	110.5 (3)	O2—C9—N2	121.3 (2)
C3—C2—H2B	109.5	O2—C9—C8	121.0 (2)
C1—C2—H2B	109.5	N2—C9—C8	117.7 (2)
C3—C2—H2C	109.5	N2—C10—C11	113.6 (2)
C1—C2—H2C	109.5	N2—C10—H10A	108.8
H2B—C2—H2C	108.1	C11—C10—H10A	108.8
C4—C3—C2	110.5 (3)	N2—C10—H10B	108.8
C4—C3—H3A	109.6	C11—C10—H10B	108.8
C2—C3—H3A	109.6	H10A—C10—H10B	107.7
C4—C3—H3B	109.6	C12—C11—C10	113.2 (2)
C2—C3—H3B	109.6	C12—C11—H11A	108.9
H3A—C3—H3B	108.1	C10—C11—H11A	108.9
C5—C4—C3	111.0 (2)	C12—C11—H11B	108.9
C5—C4—H4A	109.4	C10—C11—H11B	108.9
C3—C4—H4A	109.4	H11A—C11—H11B	107.8
C5—C4—H4B	109.4	C11—C12—C13	114.7 (2)
C3—C4—H4B	109.4	C11—C12—H12A	108.6
H4A—C4—H4B	108.0	C13—C12—H12A	108.6
C4—C5—C6	112.5 (2)	C11—C12—H12B	108.6
C4—C5—H5A	109.1	C13—C12—H12B	108.6
C6—C5—H5A	109.1	H12A—C12—H12B	107.6
C4—C5—H5B	109.1	C12—C13—C8	116.1 (2)
C6—C5—H5B	109.1	C12—C13—H13A	108.3
H5A—C5—H5B	107.8	C8—C13—H13A	108.3
C5—C6—C7	111.7 (2)	C12—C13—H13B	108.3
C5—C6—C1	110.5 (2)	C8—C13—H13B	108.3
C7—C6—C1	109.0 (2)	H13A—C13—H13B	107.4
C6—C1—C2—C3	−57.4 (3)	C7—N1—C8—C9	−150.4 (2)
C1—C2—C3—C4	57.9 (3)	C7—N1—C8—C13	85.5 (3)
C2—C3—C4—C5	−56.5 (4)	C10—N2—C9—O2	179.3 (2)
C3—C4—C5—C6	55.4 (4)	C10—N2—C9—C8	−0.4 (4)
C4—C5—C6—C7	−176.0 (2)	N1—C8—C9—O2	−4.5 (3)
C4—C5—C6—C1	−54.5 (3)	C13—C8—C9—O2	117.8 (3)
C2—C1—C6—C5	55.1 (3)	N1—C8—C9—N2	175.3 (2)
C2—C1—C6—C7	178.2 (2)	C13—C8—C9—N2	−62.5 (3)
C8—N1—C7—O1	3.9 (4)	C9—N2—C10—C11	65.1 (3)
C8—N1—C7—C6	−174.2 (2)	N2—C10—C11—C12	−78.0 (3)
C5—C6—C7—O1	51.0 (3)	C10—C11—C12—C13	62.3 (3)
C1—C6—C7—O1	−71.4 (3)	C11—C12—C13—C8	−63.3 (3)
C5—C6—C7—N1	−131.0 (3)	N1—C8—C13—C12	−160.1 (2)
C1—C6—C7—N1	106.7 (3)	C9—C8—C13—C12	78.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.37	3.158 (3)	152
N2—H2A···O2ii	0.86	2.09	2.927 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.37	3.158 (3)	152
N2—H2A⋯O2ii	0.86	2.09	2.927 (3)	165

Symmetry codes: (i) ; (ii) .