6',7'-Dimeth-oxy-1',2'-dihydro-spiro-[cyclo-hexane-1,2'-quinazolin]-4'(3'H)-one.

In the title compound, C(15)H(20)N(2)O(3), prepared from the reaction of 2-amino-4,5-dimeth-oxy-benzonitrile and cyclo-hexa-none, the six-membered diaza ring assumes an envelope conformation. In the crystal, inversion dimers are formed by pairs of N-H⋯O hydrogen bonds. Futher N-H⋯O hydrogen bonds link the dimers into a two-dimensional structure parallel to (001).

Related literature

For further information on the title compound, see: Chen et al. (2007 ▶). For related structures, see: Zhang et al. (2008 ▶). For the biological activity of related compounds, see: Hour et al. (2000 ▶).

Experimental

Crystal data

C15H20N2O3

M = 276.33

Monoclinic,

a = 11.667 (2) Å

b = 9.6376 (19) Å

c = 12.307 (3) Å

β = 101.02 (3)°

V = 1358.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 113 K

0.14 × 0.12 × 0.10 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2004 ▶) T min = 0.987, T max = 0.991

16366 measured reflections

3224 independent reflections

2759 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.09

3224 reflections

192 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku, 2004 ▶); 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: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811048732/bg2428sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048732/bg2428Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048732/bg2428Isup4.cdx

Supplementary material file. DOI: 10.1107/S1600536811048732/bg2428Isup4.cml

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

C15H20N2O3	F(000) = 592
Mr = 276.33	Dx = 1.351 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3746 reflections
a = 11.667 (2) Å	θ = 1.8–27.9°
b = 9.6376 (19) Å	µ = 0.10 mm−1
c = 12.307 (3) Å	T = 113 K
β = 101.02 (3)°	Prism, colourless
V = 1358.3 (5) Å3	0.14 × 0.12 × 0.10 mm
Z = 4

Rigaku Saturn diffractometer	3224 independent reflections
Radiation source: rotating anode	2759 reflections with I > 2σ(I)
confocal	Rint = 0.031
ω scans	θmax = 27.9°, θmin = 1.8°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2004)	h = −15→14
Tmin = 0.987, Tmax = 0.991	k = −12→12
16366 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0565P)2 + 0.1742P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
3224 reflections	Δρmax = 0.33 e Å−3
192 parameters	Δρmin = −0.18 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.073 (6)

Experimental. Mp. 251–252°C. IR (KBr, cm-1): 3290, 3220, 2930, 2838, 1651, 1619, 1507; 1H NMR (400 MHz, DMSO-d6) δH: 1.23–1.78 (10H, m, C5H10), 3.66(3H, s, OCH3), 3.74(3H, s, OCH3), 6.34 (1H, s, NH), 6.54 (1H, s, ArH), 7.07 (1H, s, ArH), 7.68 (1H, s, NH); 13 C NMR (100 MHz, DMSO-d6) δC: 21.1 (2 C), 24.8, 37.0 (2 C), 55.4, 56.0, 68.2, 99.2, 106.0, 110.0, 141.1, 142.6, 153.9, 163.4; MS (ESI): m/z (%) = 277.2 (100) [M+H]+; Anal. Calcd. for C15H20N2O3: C 65.20, H 7.30, N 10.14; found C 64.98, H 7.80, N 9.52.

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	−0.16045 (6)	0.43728 (8)	0.80668 (6)	0.0203 (2)
O2	−0.06468 (6)	0.26156 (8)	0.95294 (6)	0.0205 (2)
O3	0.37247 (6)	0.40011 (8)	1.03202 (6)	0.0200 (2)
N1	0.21715 (7)	0.61646 (9)	0.76365 (7)	0.0153 (2)
N2	0.38438 (7)	0.54041 (10)	0.88635 (7)	0.0158 (2)
C1	0.14797 (9)	0.52723 (11)	0.81032 (8)	0.0134 (2)
C2	0.02567 (9)	0.52808 (11)	0.77773 (8)	0.0145 (2)
H2A	−0.0099	0.5871	0.7215	0.017*
C3	−0.04157 (9)	0.44150 (11)	0.82915 (8)	0.0151 (2)
C4	0.01161 (9)	0.34735 (11)	0.91200 (8)	0.0152 (2)
C5	0.13085 (9)	0.34881 (11)	0.94579 (8)	0.0153 (2)
H5	0.1660	0.2894	1.0020	0.018*
C6	0.20027 (9)	0.43927 (11)	0.89624 (8)	0.0142 (2)
C7	−0.22059 (9)	0.54426 (13)	0.73899 (10)	0.0226 (3)
H7A	−0.1917	0.6330	0.7673	0.034*
H7B	−0.3026	0.5382	0.7394	0.034*
H7C	−0.2080	0.5337	0.6646	0.034*
C8	−0.01742 (10)	0.18413 (12)	1.04951 (9)	0.0199 (2)
H8A	0.0375	0.1175	1.0321	0.030*
H8B	−0.0793	0.1368	1.0756	0.030*
H8C	0.0214	0.2459	1.1059	0.030*
C9	0.32557 (9)	0.45515 (11)	0.94320 (8)	0.0152 (2)
C10	0.33946 (9)	0.57909 (11)	0.77095 (8)	0.0134 (2)
C11	0.40780 (9)	0.70426 (11)	0.74216 (8)	0.0152 (2)
H11A	0.4907	0.6843	0.7621	0.018*
H11B	0.3916	0.7831	0.7859	0.018*
C12	0.37805 (9)	0.74296 (11)	0.61959 (9)	0.0170 (2)
H12A	0.2979	0.7751	0.6015	0.020*
H12B	0.4283	0.8182	0.6051	0.020*
C13	0.39356 (10)	0.61926 (13)	0.54656 (9)	0.0222 (3)
H13A	0.4756	0.5946	0.5580	0.027*
H13B	0.3685	0.6448	0.4694	0.027*
C14	0.32319 (10)	0.49419 (12)	0.57250 (9)	0.0207 (3)
H14A	0.2405	0.5153	0.5532	0.025*
H14B	0.3387	0.4156	0.5282	0.025*
C15	0.35496 (9)	0.45662 (11)	0.69493 (9)	0.0164 (2)
H15A	0.4356	0.4258	0.7118	0.020*
H15B	0.3062	0.3801	0.7098	0.020*
H1	0.1830 (11)	0.6677 (13)	0.7058 (9)	0.029 (4)*
H2	0.4604 (8)	0.5564 (14)	0.9151 (11)	0.032 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0111 (4)	0.0221 (4)	0.0265 (4)	−0.0010 (3)	0.0004 (3)	0.0047 (3)
O2	0.0161 (4)	0.0231 (4)	0.0215 (4)	−0.0058 (3)	0.0013 (3)	0.0065 (3)
O3	0.0163 (4)	0.0240 (4)	0.0179 (4)	−0.0021 (3)	−0.0015 (3)	0.0081 (3)
N1	0.0115 (4)	0.0175 (5)	0.0169 (4)	0.0020 (3)	0.0028 (3)	0.0055 (4)
N2	0.0115 (4)	0.0201 (5)	0.0145 (4)	−0.0026 (4)	−0.0007 (3)	0.0032 (4)
C1	0.0146 (5)	0.0130 (5)	0.0130 (5)	−0.0005 (4)	0.0036 (4)	−0.0014 (4)
C2	0.0158 (5)	0.0141 (5)	0.0129 (5)	0.0015 (4)	0.0015 (4)	0.0000 (4)
C3	0.0116 (5)	0.0165 (5)	0.0163 (5)	−0.0009 (4)	0.0007 (4)	−0.0036 (4)
C4	0.0162 (5)	0.0141 (5)	0.0158 (5)	−0.0035 (4)	0.0041 (4)	−0.0013 (4)
C5	0.0171 (5)	0.0147 (5)	0.0136 (5)	−0.0001 (4)	0.0016 (4)	0.0011 (4)
C6	0.0131 (5)	0.0147 (5)	0.0141 (5)	−0.0003 (4)	0.0013 (4)	−0.0005 (4)
C7	0.0140 (5)	0.0258 (6)	0.0260 (6)	0.0026 (4)	−0.0012 (4)	0.0029 (5)
C8	0.0219 (6)	0.0187 (5)	0.0185 (5)	−0.0053 (4)	0.0029 (4)	0.0029 (4)
C9	0.0149 (5)	0.0148 (5)	0.0157 (5)	−0.0007 (4)	0.0019 (4)	0.0003 (4)
C10	0.0108 (5)	0.0156 (5)	0.0134 (5)	0.0002 (4)	0.0011 (4)	0.0024 (4)
C11	0.0139 (5)	0.0152 (5)	0.0167 (5)	−0.0022 (4)	0.0030 (4)	0.0003 (4)
C12	0.0173 (5)	0.0172 (5)	0.0172 (5)	−0.0012 (4)	0.0047 (4)	0.0029 (4)
C13	0.0266 (6)	0.0246 (6)	0.0173 (5)	−0.0009 (5)	0.0089 (5)	0.0000 (4)
C14	0.0243 (6)	0.0207 (6)	0.0173 (5)	−0.0013 (5)	0.0049 (4)	−0.0036 (4)
C15	0.0162 (5)	0.0138 (5)	0.0195 (5)	0.0009 (4)	0.0038 (4)	0.0002 (4)

O1—C3	1.3619 (12)	C7—H7B	0.9600
O1—C7	1.4233 (13)	C7—H7C	0.9600
O2—C4	1.3789 (12)	C8—H8A	0.9600
O2—C8	1.4223 (13)	C8—H8B	0.9600
O3—C9	1.2438 (13)	C8—H8C	0.9600
N1—C1	1.3777 (13)	C10—C11	1.5246 (14)
N1—C10	1.4577 (13)	C10—C15	1.5381 (14)
N1—H1	0.895 (8)	C11—C12	1.5280 (14)
N2—C9	1.3487 (14)	C11—H11A	0.9700
N2—C10	1.4650 (13)	C11—H11B	0.9700
N2—H2	0.903 (9)	C12—C13	1.5246 (16)
C1—C6	1.4009 (14)	C12—H12A	0.9700
C1—C2	1.4064 (14)	C12—H12B	0.9700
C2—C3	1.3791 (15)	C13—C14	1.5261 (16)
C2—H2A	0.9300	C13—H13A	0.9700
C3—C4	1.4164 (15)	C13—H13B	0.9700
C4—C5	1.3737 (15)	C14—C15	1.5250 (15)
C5—C6	1.4060 (14)	C14—H14A	0.9700
C5—H5	0.9300	C14—H14B	0.9700
C6—C9	1.4735 (14)	C15—H15A	0.9700
C7—H7A	0.9600	C15—H15B	0.9700
C3—O1—C7	117.79 (9)	O3—C9—C6	122.49 (10)
C4—O2—C8	116.47 (8)	N2—C9—C6	115.13 (9)
C1—N1—C10	117.69 (8)	N1—C10—N2	106.68 (8)
C1—N1—H1	118.0 (9)	N1—C10—C11	109.84 (8)
C10—N1—H1	117.8 (9)	N2—C10—C11	108.70 (8)
C9—N2—C10	122.33 (9)	N1—C10—C15	112.31 (9)
C9—N2—H2	117.4 (9)	N2—C10—C15	109.43 (8)
C10—N2—H2	118.6 (9)	C11—C10—C15	109.77 (8)
N1—C1—C6	119.15 (9)	C10—C11—C12	113.10 (8)
N1—C1—C2	121.38 (9)	C10—C11—H11A	109.0
C6—C1—C2	119.37 (9)	C12—C11—H11A	109.0
C3—C2—C1	120.05 (10)	C10—C11—H11B	109.0
C3—C2—H2A	120.0	C12—C11—H11B	109.0
C1—C2—H2A	120.0	H11A—C11—H11B	107.8
O1—C3—C2	124.84 (10)	C13—C12—C11	111.16 (9)
O1—C3—C4	114.59 (9)	C13—C12—H12A	109.4
C2—C3—C4	120.57 (9)	C11—C12—H12A	109.4
C5—C4—O2	125.64 (9)	C13—C12—H12B	109.4
C5—C4—C3	119.36 (10)	C11—C12—H12B	109.4
O2—C4—C3	115.00 (9)	H12A—C12—H12B	108.0
C4—C5—C6	120.60 (10)	C12—C13—C14	111.41 (9)
C4—C5—H5	119.7	C12—C13—H13A	109.3
C6—C5—H5	119.7	C14—C13—H13A	109.3
C1—C6—C5	119.92 (9)	C12—C13—H13B	109.3
C1—C6—C9	119.31 (9)	C14—C13—H13B	109.3
C5—C6—C9	120.32 (9)	H13A—C13—H13B	108.0
O1—C7—H7A	109.5	C15—C14—C13	110.82 (9)
O1—C7—H7B	109.5	C15—C14—H14A	109.5
H7A—C7—H7B	109.5	C13—C14—H14A	109.5
O1—C7—H7C	109.5	C15—C14—H14B	109.5
H7A—C7—H7C	109.5	C13—C14—H14B	109.5
H7B—C7—H7C	109.5	H14A—C14—H14B	108.1
O2—C8—H8A	109.5	C14—C15—C10	112.59 (9)
O2—C8—H8B	109.5	C14—C15—H15A	109.1
H8A—C8—H8B	109.5	C10—C15—H15A	109.1
O2—C8—H8C	109.5	C14—C15—H15B	109.1
H8A—C8—H8C	109.5	C10—C15—H15B	109.1
H8B—C8—H8C	109.5	H15A—C15—H15B	107.8
O3—C9—N2	122.27 (9)
C10—N1—C1—C6	24.75 (14)	C10—N2—C9—O3	165.20 (10)
C10—N1—C1—C2	−158.81 (9)	C10—N2—C9—C6	−18.58 (14)
N1—C1—C2—C3	−177.33 (9)	C1—C6—C9—O3	165.95 (10)
C6—C1—C2—C3	−0.90 (15)	C5—C6—C9—O3	−6.30 (16)
C7—O1—C3—C2	−10.82 (15)	C1—C6—C9—N2	−10.26 (14)
C7—O1—C3—C4	169.32 (9)	C5—C6—C9—N2	177.49 (9)
C1—C2—C3—O1	177.71 (9)	C1—N1—C10—N2	−48.06 (12)
C1—C2—C3—C4	−2.43 (15)	C1—N1—C10—C11	−165.70 (9)
C8—O2—C4—C5	10.36 (15)	C1—N1—C10—C15	71.83 (11)
C8—O2—C4—C3	−168.79 (9)	C9—N2—C10—N1	46.21 (13)
O1—C3—C4—C5	−176.12 (9)	C9—N2—C10—C11	164.60 (9)
C2—C3—C4—C5	4.01 (15)	C9—N2—C10—C15	−75.52 (12)
O1—C3—C4—O2	3.09 (13)	N1—C10—C11—C12	−70.47 (11)
C2—C3—C4—O2	−176.78 (9)	N2—C10—C11—C12	173.15 (8)
O2—C4—C5—C6	178.66 (9)	C15—C10—C11—C12	53.49 (11)
C3—C4—C5—C6	−2.21 (15)	C10—C11—C12—C13	−54.58 (12)
N1—C1—C6—C5	179.18 (9)	C11—C12—C13—C14	54.73 (12)
C2—C1—C6—C5	2.67 (15)	C12—C13—C14—C15	−55.51 (12)
N1—C1—C6—C9	6.90 (14)	C13—C14—C15—C10	55.82 (12)
C2—C1—C6—C9	−169.61 (9)	N1—C10—C15—C14	68.32 (11)
C4—C5—C6—C1	−1.10 (15)	N2—C10—C15—C14	−173.39 (8)
C4—C5—C6—C9	171.11 (9)	C11—C10—C15—C14	−54.19 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3i	0.90 (1)	1.98 (1)	2.8801 (13)	176.(1)
N1—H1···O2ii	0.90 (1)	2.35 (1)	3.2267 (14)	168.(1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3i	0.90 (1)	1.98 (1)	2.8801 (13)	176 (1)
N1—H1⋯O2ii	0.90 (1)	2.35 (1)	3.2267 (14)	168 (1)

Symmetry codes: (i) ; (ii) .