6'-Methyl-1',2',3',4'-tetra-hydro-spiro-cyclo-hexane-2'-quinazolin-4'-one.

The title compound, C(14)H(18)N(2)O, was synthesized by the reaction of cyclo-hexa-none and 2-amino-5-methyl-benzonitrile. In the mol-ecule, the cyclo-hexane ring displays a chair conformation, whereas the 1,3-diaza-cyclo-hexane moiety of the bicyclic system has a sofa conformation with the spiro C atom displaced by 0.603 (2) Å from the rest of the atoms of the 1,3-diaza-cyclo-hexane ring [planar within 0.052 (2) Å]. Mol-ecules are linked into centrosymmetric dimers via N-H⋯O hydrogen bonds.

Related literature

For medicinal and biological properties of dihydro­quinazolin-4(3H)-one derivatives, see: Jackson et al. (2007 ▶); Shi et al. (2003 ▶, 2004 ▶).

Experimental

Crystal data

C14H18N2O

M = 230.30

Monoclinic,

a = 9.4077 (19) Å

b = 11.853 (2) Å

c = 11.067 (2) Å

β = 106.44 (3)°

V = 1183.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 113 K

0.28 × 0.24 × 0.20 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.977, T max = 0.984

14356 measured reflections

2810 independent reflections

2346 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.09

2810 reflections

163 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); 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/S1600536809014111/ya2085sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014111/ya2085Isup2.hkl

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

C14H18N2O	F(000) = 496
Mr = 230.30	Dx = 1.292 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3810 reflections
a = 9.4077 (19) Å	θ = 1.7–27.9°
b = 11.853 (2) Å	µ = 0.08 mm−1
c = 11.067 (2) Å	T = 113 K
β = 106.44 (3)°	Cube, colorless
V = 1183.6 (4) Å3	0.28 × 0.24 × 0.20 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	2810 independent reflections
Radiation source: rotating anode	2346 reflections with I > 2σ(I)
confocal	Rint = 0.034
Detector resolution: 7.31 pixels mm-1	θmax = 27.9°, θmin = 2.5°
ω and φ scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −15→15
Tmin = 0.977, Tmax = 0.984	l = −14→14
14356 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0601P)2 + 0.2329P] where P = (Fo2 + 2Fc2)/3
2810 reflections	(Δ/σ)max = 0.003
163 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.26 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	0.01942 (8)	0.42294 (7)	0.36579 (7)	0.0182 (2)
N1	0.32706 (11)	0.24403 (8)	0.61566 (9)	0.0167 (2)
N2	0.16255 (10)	0.39739 (8)	0.56703 (8)	0.0144 (2)
C1	0.31997 (12)	0.22860 (9)	0.49040 (10)	0.0153 (2)
C2	0.39770 (12)	0.14331 (9)	0.44884 (11)	0.0191 (2)
H2	0.4588	0.0928	0.5078	0.023*
C3	0.38557 (12)	0.13253 (9)	0.32154 (11)	0.0197 (2)
H3	0.4379	0.0736	0.2946	0.024*
C4	0.29853 (12)	0.20585 (9)	0.23162 (10)	0.0180 (2)
C5	0.21867 (12)	0.28808 (9)	0.27333 (10)	0.0163 (2)
H5	0.1573	0.3381	0.2139	0.020*
C6	0.22636 (11)	0.29905 (9)	0.40055 (10)	0.0143 (2)
C7	0.12913 (11)	0.37917 (9)	0.44220 (10)	0.0141 (2)
C8	0.29082 (14)	0.19553 (11)	0.09415 (11)	0.0268 (3)
H8A	0.2017	0.2339	0.0431	0.040*
H8B	0.2869	0.1156	0.0707	0.040*
H8C	0.3789	0.2304	0.0793	0.040*
C9	0.30268 (11)	0.35816 (9)	0.65516 (9)	0.0142 (2)
C10	0.28781 (13)	0.35125 (9)	0.78910 (10)	0.0176 (2)
H10A	0.1961	0.3095	0.7872	0.021*
H10B	0.3726	0.3080	0.8423	0.021*
C11	0.28289 (12)	0.46671 (10)	0.84905 (10)	0.0192 (2)
H11A	0.2840	0.4566	0.9381	0.023*
H11B	0.1895	0.5055	0.8046	0.023*
C12	0.41467 (13)	0.53975 (10)	0.84304 (10)	0.0215 (3)
H12A	0.4071	0.6148	0.8799	0.026*
H12B	0.5081	0.5040	0.8927	0.026*
C13	0.41659 (13)	0.55324 (10)	0.70664 (10)	0.0204 (3)
H13A	0.5013	0.6013	0.7029	0.024*
H13B	0.3242	0.5906	0.6574	0.024*
C14	0.43013 (12)	0.43771 (9)	0.64986 (10)	0.0169 (2)
H14A	0.5257	0.4030	0.6963	0.020*
H14B	0.4303	0.4474	0.5610	0.020*
H2A	0.1067 (16)	0.4493 (13)	0.5919 (13)	0.027 (4)*
H1	0.3942 (18)	0.2055 (13)	0.6744 (14)	0.031 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0160 (4)	0.0208 (4)	0.0164 (4)	0.0053 (3)	0.0024 (3)	0.0005 (3)
N1	0.0198 (5)	0.0136 (5)	0.0159 (5)	0.0048 (4)	0.0040 (4)	0.0011 (3)
N2	0.0131 (4)	0.0143 (4)	0.0157 (4)	0.0030 (3)	0.0039 (3)	−0.0006 (3)
C1	0.0143 (5)	0.0135 (5)	0.0181 (5)	−0.0014 (4)	0.0048 (4)	−0.0013 (4)
C2	0.0187 (5)	0.0154 (5)	0.0226 (6)	0.0040 (4)	0.0045 (4)	−0.0011 (4)
C3	0.0175 (5)	0.0178 (5)	0.0247 (6)	0.0007 (4)	0.0073 (4)	−0.0065 (4)
C4	0.0153 (5)	0.0199 (6)	0.0192 (5)	−0.0034 (4)	0.0058 (4)	−0.0052 (4)
C5	0.0135 (5)	0.0171 (5)	0.0176 (5)	−0.0014 (4)	0.0034 (4)	−0.0018 (4)
C6	0.0124 (5)	0.0126 (5)	0.0178 (5)	−0.0014 (4)	0.0042 (4)	−0.0015 (4)
C7	0.0124 (5)	0.0128 (5)	0.0172 (5)	−0.0012 (4)	0.0045 (4)	0.0005 (4)
C8	0.0291 (6)	0.0327 (7)	0.0198 (6)	0.0046 (5)	0.0090 (5)	−0.0052 (5)
C9	0.0140 (5)	0.0135 (5)	0.0142 (5)	0.0020 (4)	0.0027 (4)	−0.0001 (4)
C10	0.0207 (5)	0.0178 (5)	0.0148 (5)	0.0019 (4)	0.0056 (4)	0.0020 (4)
C11	0.0196 (5)	0.0226 (6)	0.0144 (5)	0.0036 (4)	0.0031 (4)	−0.0017 (4)
C12	0.0196 (6)	0.0231 (6)	0.0186 (5)	0.0002 (5)	0.0004 (4)	−0.0059 (4)
C13	0.0196 (5)	0.0175 (6)	0.0224 (6)	−0.0032 (4)	0.0033 (4)	−0.0012 (4)
C14	0.0140 (5)	0.0183 (5)	0.0180 (5)	−0.0009 (4)	0.0042 (4)	−0.0003 (4)

O1—C7	1.2472 (13)	C8—H8B	0.9800
N1—C1	1.3810 (14)	C8—H8C	0.9800
N1—C9	1.4596 (14)	C9—C10	1.5299 (14)
N1—H1	0.893 (16)	C9—C14	1.5394 (15)
N2—C7	1.3446 (13)	C10—C11	1.5273 (16)
N2—C9	1.4757 (14)	C10—H10A	0.9900
N2—H2A	0.901 (16)	C10—H10B	0.9900
C1—C2	1.3995 (15)	C11—C12	1.5289 (16)
C1—C6	1.4022 (15)	C11—H11A	0.9900
C2—C3	1.3867 (15)	C11—H11B	0.9900
C2—H2	0.9500	C12—C13	1.5232 (16)
C3—C4	1.3982 (17)	C12—H12A	0.9900
C3—H3	0.9500	C12—H12B	0.9900
C4—C5	1.3870 (15)	C13—C14	1.5269 (15)
C4—C8	1.5074 (15)	C13—H13A	0.9900
C5—C6	1.3953 (14)	C13—H13B	0.9900
C5—H5	0.9500	C14—H14A	0.9900
C6—C7	1.4797 (14)	C14—H14B	0.9900
C8—H8A	0.9800
C1—N1—C9	117.15 (9)	N2—C9—C10	110.35 (9)
C1—N1—H1	119.1 (10)	N1—C9—C14	111.48 (9)
C9—N1—H1	113.2 (10)	N2—C9—C14	109.97 (8)
C7—N2—C9	122.26 (9)	C10—C9—C14	110.82 (9)
C7—N2—H2A	115.9 (9)	C11—C10—C9	113.28 (9)
C9—N2—H2A	120.1 (9)	C11—C10—H10A	108.9
N1—C1—C2	122.97 (10)	C9—C10—H10A	108.9
N1—C1—C6	118.37 (10)	C11—C10—H10B	108.9
C2—C1—C6	118.61 (10)	C9—C10—H10B	108.9
C3—C2—C1	120.00 (10)	H10A—C10—H10B	107.7
C3—C2—H2	120.0	C10—C11—C12	111.34 (9)
C1—C2—H2	120.0	C10—C11—H11A	109.4
C2—C3—C4	121.94 (10)	C12—C11—H11A	109.4
C2—C3—H3	119.0	C10—C11—H11B	109.4
C4—C3—H3	119.0	C12—C11—H11B	109.4
C5—C4—C3	117.59 (10)	H11A—C11—H11B	108.0
C5—C4—C8	121.13 (10)	C13—C12—C11	109.86 (9)
C3—C4—C8	121.28 (10)	C13—C12—H12A	109.7
C4—C5—C6	121.54 (10)	C11—C12—H12A	109.7
C4—C5—H5	119.2	C13—C12—H12B	109.7
C6—C5—H5	119.2	C11—C12—H12B	109.7
C5—C6—C1	120.19 (10)	H12A—C12—H12B	108.2
C5—C6—C7	120.94 (9)	C12—C13—C14	109.84 (9)
C1—C6—C7	118.74 (9)	C12—C13—H13A	109.7
O1—C7—N2	122.54 (10)	C14—C13—H13A	109.7
O1—C7—C6	121.44 (9)	C12—C13—H13B	109.7
N2—C7—C6	115.95 (9)	C14—C13—H13B	109.7
C4—C8—H8A	109.5	H13A—C13—H13B	108.2
C4—C8—H8B	109.5	C13—C14—C9	112.16 (9)
H8A—C8—H8B	109.5	C13—C14—H14A	109.2
C4—C8—H8C	109.5	C9—C14—H14A	109.2
H8A—C8—H8C	109.5	C13—C14—H14B	109.2
H8B—C8—H8C	109.5	C9—C14—H14B	109.2
N1—C9—N2	106.31 (8)	H14A—C14—H14B	107.9
N1—C9—C10	107.80 (8)
C9—N1—C1—C2	152.24 (10)	C5—C6—C7—N2	−168.95 (9)
C9—N1—C1—C6	−30.19 (14)	C1—C6—C7—N2	15.21 (14)
N1—C1—C2—C3	179.98 (10)	C1—N1—C9—N2	51.63 (12)
C6—C1—C2—C3	2.41 (16)	C1—N1—C9—C10	169.95 (9)
C1—C2—C3—C4	0.84 (17)	C1—N1—C9—C14	−68.21 (12)
C2—C3—C4—C5	−2.60 (16)	C7—N2—C9—N1	−42.79 (13)
C2—C3—C4—C8	177.80 (11)	C7—N2—C9—C10	−159.42 (9)
C3—C4—C5—C6	1.10 (16)	C7—N2—C9—C14	78.03 (12)
C8—C4—C5—C6	−179.30 (10)	N1—C9—C10—C11	172.15 (9)
C4—C5—C6—C1	2.13 (16)	N2—C9—C10—C11	−72.16 (11)
C4—C5—C6—C7	−173.64 (10)	C14—C9—C10—C11	49.90 (12)
N1—C1—C6—C5	178.45 (9)	C9—C10—C11—C12	−53.09 (12)
C2—C1—C6—C5	−3.87 (16)	C10—C11—C12—C13	57.52 (12)
N1—C1—C6—C7	−5.69 (15)	C11—C12—C13—C14	−60.01 (12)
C2—C1—C6—C7	171.99 (9)	C12—C13—C14—C9	58.30 (12)
C9—N2—C7—O1	−171.57 (10)	N1—C9—C14—C13	−172.67 (8)
C9—N2—C7—C6	11.38 (14)	N2—C9—C14—C13	69.67 (11)
C5—C6—C7—O1	13.96 (15)	C10—C9—C14—C13	−52.60 (11)
C1—C6—C7—O1	−161.87 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1i	0.901 (16)	2.058 (16)	2.9563 (13)	174.5 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1i	0.901 (16)	2.058 (16)	2.9563 (13)	174.5 (13)

Symmetry code: (i) .