Cyclo-hexa-nespiro-2'-[2',3',6',7'-tetra-hydro-1'H-cyclo-penta-[d]pyrimidin]-4'(5'H)-one.

The title compound, C(12)H(18)N(2)O, was synthesized by the reaction of cyclo-hexa-none and 2-amino-cyclo-pent-1-enecarbonitrile. In the mol-ecule of the title compound, the six-carbon ring displays a chair conformation, the six-membered 1,3-diaza ring and the cyclo-pentene ring both assume envelope conformations. Supra-molecular aggregation is achieved by N-H⋯O hydrogen bonds.

Related literature

For general background on the biological activity of pyrimidinones, see: Schramm et al. (1984 ▶); Wen et al. (2002 ▶); For related structures, see: Yu et al. (1992 ▶); Zhang, Li, Shi et al. (2008 ▶); Zhang, Li, Yang et al. (2008 ▶).

Experimental

Crystal data

C12H18N2O

M = 206.28

Monoclinic,

a = 10.294 (2) Å

b = 10.461 (2) Å

c = 10.659 (2) Å

β = 112.70 (3)°

V = 1059.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 113 K

0.24 × 0.20 × 0.08 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006 ▶) T min = 0.980, T max = 0.993

6976 measured reflections

1862 independent reflections

1632 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.103

S = 1.13

1862 reflections

144 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809005388/pk2145sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005388/pk2145Isup2.hkl

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

C12H18N2O	F(000) = 448
Mr = 206.28	Dx = 1.294 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3035 reflections
a = 10.294 (2) Å	θ = 2.8–27.8°
b = 10.461 (2) Å	µ = 0.08 mm−1
c = 10.659 (2) Å	T = 113 K
β = 112.70 (3)°	Plate, colorless
V = 1059.0 (4) Å3	0.24 × 0.20 × 0.08 mm
Z = 4

Rigaku Saturn diffractometer	1862 independent reflections
Radiation source: rotating anode	1632 reflections with I > 2σ(I)
confocal multilayer optics	Rint = 0.034
Detector resolution: 14.63 pixels mm-1	θmax = 25.0°, θmin = 2.8°
ω scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	k = −12→12
Tmin = 0.980, Tmax = 0.993	l = −12→12
6976 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.058P)2 + 0.1813P] where P = (Fo2 + 2Fc2)/3
1862 reflections	(Δ/σ)max < 0.001
144 parameters	Δρmax = 0.22 e Å−3
2 restraints	Δρmin = −0.22 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	−0.14346 (9)	0.42583 (8)	0.02403 (9)	0.0163 (2)
N1	0.08172 (11)	0.34945 (10)	0.09960 (11)	0.0152 (3)
N2	0.16234 (11)	0.18929 (10)	0.26816 (11)	0.0165 (3)
C1	−0.05332 (13)	0.34458 (11)	0.09213 (13)	0.0137 (3)
C2	−0.08039 (13)	0.24658 (11)	0.17362 (13)	0.0152 (3)
C3	−0.21300 (13)	0.22403 (12)	0.19860 (14)	0.0179 (3)
H3A	−0.2919	0.2044	0.1147	0.021*
H3B	−0.2364	0.2976	0.2412	0.021*
C4	−0.17249 (14)	0.10798 (13)	0.29541 (15)	0.0219 (3)
H4A	−0.2158	0.1143	0.3614	0.026*
H4B	−0.2031	0.0291	0.2447	0.026*
C5	−0.01109 (13)	0.11111 (13)	0.36688 (14)	0.0196 (3)
H5A	0.0185	0.1558	0.4531	0.023*
H5B	0.0282	0.0255	0.3820	0.023*
C6	0.03058 (13)	0.18298 (11)	0.26602 (13)	0.0152 (3)
C7	0.17877 (12)	0.24061 (11)	0.14698 (13)	0.0142 (3)
C8	0.14163 (13)	0.13822 (12)	0.03476 (14)	0.0165 (3)
H8A	0.0486	0.1045	0.0181	0.020*
H8B	0.1386	0.1776	−0.0487	0.020*
C9	0.24726 (14)	0.02825 (12)	0.07214 (14)	0.0206 (3)
H9A	0.2210	−0.0323	−0.0025	0.025*
H9B	0.2451	−0.0159	0.1513	0.025*
C10	0.39614 (13)	0.07713 (13)	0.10258 (15)	0.0212 (3)
H10A	0.4621	0.0064	0.1303	0.025*
H10B	0.4007	0.1147	0.0212	0.025*
C11	0.43647 (13)	0.17692 (13)	0.21547 (14)	0.0194 (3)
H11A	0.5287	0.2112	0.2298	0.023*
H11B	0.4422	0.1364	0.2993	0.023*
C12	0.32970 (12)	0.28661 (12)	0.18128 (14)	0.0171 (3)
H12A	0.3561	0.3445	0.2582	0.021*
H12B	0.3333	0.3340	0.1045	0.021*
H1	0.1032 (15)	0.4130 (12)	0.0541 (14)	0.025 (4)*
H2	0.2347 (13)	0.1526 (15)	0.3359 (14)	0.034 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0151 (5)	0.0148 (4)	0.0169 (5)	0.0014 (4)	0.0038 (4)	0.0029 (4)
N1	0.0145 (6)	0.0128 (5)	0.0185 (6)	−0.0001 (4)	0.0066 (5)	0.0035 (5)
N2	0.0131 (6)	0.0219 (6)	0.0142 (6)	0.0028 (4)	0.0050 (5)	0.0048 (5)
C1	0.0142 (6)	0.0128 (6)	0.0121 (7)	−0.0016 (5)	0.0030 (5)	−0.0031 (5)
C2	0.0147 (6)	0.0144 (6)	0.0171 (7)	−0.0002 (5)	0.0067 (5)	0.0001 (5)
C3	0.0161 (6)	0.0178 (6)	0.0211 (7)	−0.0003 (5)	0.0087 (5)	0.0006 (6)
C4	0.0209 (7)	0.0242 (7)	0.0239 (8)	−0.0002 (6)	0.0125 (6)	0.0058 (6)
C5	0.0210 (7)	0.0214 (7)	0.0188 (8)	0.0034 (6)	0.0105 (6)	0.0054 (6)
C6	0.0178 (7)	0.0140 (6)	0.0152 (7)	−0.0009 (5)	0.0080 (5)	−0.0017 (5)
C7	0.0134 (6)	0.0146 (6)	0.0144 (7)	0.0003 (5)	0.0052 (5)	0.0021 (5)
C8	0.0161 (7)	0.0167 (6)	0.0157 (7)	−0.0015 (5)	0.0052 (5)	−0.0003 (5)
C9	0.0243 (7)	0.0160 (6)	0.0214 (8)	0.0009 (5)	0.0087 (6)	−0.0021 (5)
C10	0.0208 (7)	0.0234 (7)	0.0219 (8)	0.0052 (6)	0.0110 (6)	0.0003 (6)
C11	0.0134 (6)	0.0256 (7)	0.0197 (7)	0.0017 (5)	0.0068 (5)	−0.0002 (6)
C12	0.0151 (7)	0.0182 (6)	0.0190 (7)	−0.0021 (5)	0.0076 (5)	−0.0026 (5)

O1—C1	1.2612 (15)	C5—H5B	0.9700
N1—C1	1.3623 (16)	C7—C12	1.5299 (17)
N1—C7	1.4698 (16)	C7—C8	1.5399 (18)
N1—H1	0.899 (9)	C8—C9	1.5265 (18)
N2—C6	1.3494 (17)	C8—H8A	0.9700
N2—C7	1.4676 (17)	C8—H8B	0.9700
N2—H2	0.899 (9)	C9—C10	1.5271 (19)
C1—C2	1.4387 (17)	C9—H9A	0.9700
C2—C6	1.3599 (18)	C9—H9B	0.9700
C2—C3	1.5068 (17)	C10—C11	1.5246 (19)
C3—C4	1.5429 (19)	C10—H10A	0.9700
C3—H3A	0.9700	C10—H10B	0.9700
C3—H3B	0.9700	C11—C12	1.5324 (18)
C4—C5	1.5380 (19)	C11—H11A	0.9700
C4—H4A	0.9700	C11—H11B	0.9700
C4—H4B	0.9700	C12—H12A	0.9700
C5—C6	1.5036 (18)	C12—H12B	0.9700
C5—H5A	0.9700
C1—N1—C7	122.29 (10)	N1—C7—C12	109.36 (10)
C1—N1—H1	117.0 (9)	N2—C7—C8	110.53 (10)
C7—N1—H1	118.8 (9)	N1—C7—C8	109.86 (10)
C6—N2—C7	117.35 (11)	C12—C7—C8	109.22 (10)
C6—N2—H2	120.6 (11)	C9—C8—C7	112.53 (11)
C7—N2—H2	121.4 (11)	C9—C8—H8A	109.1
O1—C1—N1	121.07 (11)	C7—C8—H8A	109.1
O1—C1—C2	123.83 (11)	C9—C8—H8B	109.1
N1—C1—C2	114.98 (11)	C7—C8—H8B	109.1
C6—C2—C1	118.79 (11)	H8A—C8—H8B	107.8
C6—C2—C3	111.14 (11)	C8—C9—C10	111.01 (11)
C1—C2—C3	128.16 (11)	C8—C9—H9A	109.4
C2—C3—C4	102.23 (10)	C10—C9—H9A	109.4
C2—C3—H3A	111.3	C8—C9—H9B	109.4
C4—C3—H3A	111.3	C10—C9—H9B	109.4
C2—C3—H3B	111.3	H9A—C9—H9B	108.0
C4—C3—H3B	111.3	C11—C10—C9	110.02 (11)
H3A—C3—H3B	109.2	C11—C10—H10A	109.7
C5—C4—C3	106.03 (10)	C9—C10—H10A	109.7
C5—C4—H4A	110.5	C11—C10—H10B	109.7
C3—C4—H4A	110.5	C9—C10—H10B	109.7
C5—C4—H4B	110.5	H10A—C10—H10B	108.2
C3—C4—H4B	110.5	C10—C11—C12	111.91 (11)
H4A—C4—H4B	108.7	C10—C11—H11A	109.2
C6—C5—C4	102.01 (11)	C12—C11—H11A	109.2
C6—C5—H5A	111.4	C10—C11—H11B	109.2
C4—C5—H5A	111.4	C12—C11—H11B	109.2
C6—C5—H5B	111.4	H11A—C11—H11B	107.9
C4—C5—H5B	111.4	C7—C12—C11	112.98 (10)
H5A—C5—H5B	109.2	C7—C12—H12A	109.0
N2—C6—C2	123.11 (12)	C11—C12—H12A	109.0
N2—C6—C5	125.07 (11)	C7—C12—H12B	109.0
C2—C6—C5	111.77 (11)	C11—C12—H12B	109.0
N2—C7—N1	106.97 (10)	H12A—C12—H12B	107.8
N2—C7—C12	110.86 (11)
C7—N1—C1—O1	−163.93 (11)	C4—C5—C6—C2	16.59 (14)
C7—N1—C1—C2	19.87 (17)	C6—N2—C7—N1	40.32 (14)
O1—C1—C2—C6	−165.34 (12)	C6—N2—C7—C12	159.48 (11)
N1—C1—C2—C6	10.73 (17)	C6—N2—C7—C8	−79.26 (13)
O1—C1—C2—C3	−2.6 (2)	C1—N1—C7—N2	−44.20 (15)
N1—C1—C2—C3	173.52 (12)	C1—N1—C7—C12	−164.32 (11)
C6—C2—C3—C4	−15.01 (14)	C1—N1—C7—C8	75.81 (14)
C1—C2—C3—C4	−178.87 (13)	N2—C7—C8—C9	−67.76 (13)
C2—C3—C4—C5	24.67 (14)	N1—C7—C8—C9	174.42 (10)
C3—C4—C5—C6	−25.13 (14)	C12—C7—C8—C9	54.46 (14)
C7—N2—C6—C2	−15.31 (18)	C7—C8—C9—C10	−57.49 (15)
C7—N2—C6—C5	167.51 (12)	C8—C9—C10—C11	56.57 (15)
C1—C2—C6—N2	−12.96 (19)	C9—C10—C11—C12	−55.28 (15)
C3—C2—C6—N2	−178.51 (11)	N2—C7—C12—C11	69.13 (14)
C1—C2—C6—C5	164.56 (11)	N1—C7—C12—C11	−173.17 (11)
C3—C2—C6—C5	−1.00 (15)	C8—C7—C12—C11	−52.91 (15)
C4—C5—C6—N2	−165.96 (12)	C10—C11—C12—C7	54.85 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.90 (1)	1.99 (1)	2.8832 (14)	170 (1)
N2—H2···O1ii	0.90 (1)	2.08 (1)	2.9458 (17)	161 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.899 (9)	1.993 (9)	2.8832 (14)	169.9 (14)
N2—H2⋯O1ii	0.899 (9)	2.080 (11)	2.9458 (17)	161.3 (15)

Symmetry codes: (i) ; (ii) .