7'-Amino-1'H-spiro-[cyclo-heptane-1,2'-pyrimido[4,5-d]pyrimidin]-4'(3'H)-one.

The title compound, C(12)H(17)N(5)O, was obtained by cyclo-condensation of 2,4-diamino-pyrimidine-5-carbonitrile with cyclo-hepta-none. The tetra-hydro-pyrimidine ring has a dis-torted boat conformation and the cyclo-heptane ring adopts a chair conformation. In the crystal, molecules are linked via N-H⋯O and N-H⋯N hydrogen bonds generating a three-dimensional network.

Related literature

For medicinal and biological properties of 2,3-dihydro­pyrimido[4,5-d]pyrimidin-4(1H)-one derivatives, see: Gebauer et al. (2003 ▶); McDermott et al. (2006 ▶). For a related structure, see: Shi et al. (2010 ▶).

Experimental

Crystal data

C12H17N5O

M = 247.31

Monoclinic,

a = 10.798 (3) Å

b = 10.365 (3) Å

c = 11.341 (3) Å

β = 110.287 (4)°

V = 1190.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 153 K

0.39 × 0.35 × 0.26 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

9163 measured reflections

3450 independent reflections

3237 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.129

S = 1.00

3450 reflections

180 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2009 ▶); 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: CrystalStructure (Rigaku/MSC, 2009 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812031492/cv5317sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031492/cv5317Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031492/cv5317Isup3.cml

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

C12H17N5O	F(000) = 528
Mr = 247.31	Dx = 1.380 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.798 (3) Å	Cell parameters from 4105 reflections
b = 10.365 (3) Å	θ = 2.0–30.0°
c = 11.341 (3) Å	µ = 0.09 mm−1
β = 110.287 (4)°	T = 153 K
V = 1190.5 (6) Å3	Block, colourless
Z = 4	0.39 × 0.35 × 0.26 mm

Rigaku AFC10/Saturn724+ diffractometer	3237 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.036
Graphite monochromator	θmax = 30.0°, θmin = 2.2°
Detector resolution: 28.5714 pixels mm-1	h = −15→15
phi and ω scans	k = −14→10
9163 measured reflections	l = −9→15
3450 independent reflections

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)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.129	w = 1/[σ2(Fo2) + (0.0495P)2 + 0.960P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
3450 reflections	Δρmax = 0.35 e Å−3
180 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0058 (19)

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	0.50270 (10)	0.09029 (10)	0.36576 (9)	0.0190 (2)
N1	0.59501 (11)	0.15243 (11)	0.56975 (10)	0.0168 (2)
N2	0.76803 (11)	0.30528 (12)	0.63161 (10)	0.0180 (2)
N3	0.83812 (11)	0.40875 (11)	0.48490 (10)	0.0175 (2)
N4	0.71560 (11)	0.38221 (12)	0.26293 (10)	0.0190 (2)
N5	0.90263 (12)	0.50418 (13)	0.33343 (12)	0.0217 (3)
C1	0.55839 (13)	0.36082 (13)	0.65798 (12)	0.0190 (3)
H1A	0.6087	0.4380	0.6996	0.023*
H1B	0.5115	0.3832	0.5687	0.023*
C2	0.45569 (14)	0.33082 (16)	0.71849 (13)	0.0235 (3)
H2A	0.4361	0.2372	0.7106	0.028*
H2B	0.3730	0.3774	0.6723	0.028*
C3	0.50040 (16)	0.36863 (18)	0.85753 (14)	0.0302 (4)
H3A	0.5270	0.4605	0.8652	0.036*
H3B	0.4239	0.3608	0.8861	0.036*
C4	0.61375 (15)	0.29004 (18)	0.94541 (13)	0.0281 (3)
H4A	0.5803	0.2028	0.9536	0.034*
H4B	0.6421	0.3307	1.0296	0.034*
C5	0.73471 (14)	0.27534 (16)	0.90615 (12)	0.0235 (3)
H5A	0.8085	0.2403	0.9779	0.028*
H5B	0.7615	0.3617	0.8862	0.028*
C6	0.71173 (14)	0.18714 (14)	0.79249 (12)	0.0198 (3)
H6A	0.6495	0.1182	0.7958	0.024*
H6B	0.7966	0.1452	0.8002	0.024*
C7	0.65745 (12)	0.25199 (13)	0.66346 (11)	0.0150 (2)
C8	0.57409 (12)	0.16677 (13)	0.44658 (12)	0.0153 (2)
C9	0.64680 (12)	0.27115 (13)	0.41465 (12)	0.0158 (2)
C10	0.75182 (12)	0.33111 (13)	0.51061 (12)	0.0154 (2)
C11	0.81680 (12)	0.42899 (13)	0.36179 (12)	0.0167 (3)
C12	0.63510 (13)	0.30267 (13)	0.29228 (12)	0.0177 (3)
H12	0.5650	0.2648	0.2256	0.021*
H2N	0.8326 (19)	0.3443 (19)	0.6896 (18)	0.026 (5)*
H0A	0.9754 (19)	0.5290 (18)	0.3921 (18)	0.023 (4)*
H0B	0.893 (2)	0.514 (2)	0.257 (2)	0.033 (5)*
H1N	0.557 (2)	0.087 (2)	0.593 (2)	0.035 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0220 (5)	0.0204 (5)	0.0161 (4)	−0.0067 (4)	0.0087 (4)	−0.0042 (3)
N1	0.0218 (5)	0.0164 (5)	0.0142 (5)	−0.0044 (4)	0.0089 (4)	−0.0008 (4)
N2	0.0165 (5)	0.0254 (6)	0.0122 (5)	−0.0068 (4)	0.0050 (4)	−0.0011 (4)
N3	0.0180 (5)	0.0208 (6)	0.0151 (5)	−0.0047 (4)	0.0075 (4)	−0.0006 (4)
N4	0.0220 (5)	0.0207 (6)	0.0147 (5)	−0.0036 (4)	0.0066 (4)	0.0003 (4)
N5	0.0217 (6)	0.0278 (6)	0.0166 (5)	−0.0085 (5)	0.0077 (4)	0.0009 (5)
C1	0.0207 (6)	0.0194 (6)	0.0166 (6)	0.0011 (5)	0.0062 (5)	−0.0008 (5)
C2	0.0193 (6)	0.0331 (8)	0.0189 (6)	0.0024 (5)	0.0076 (5)	−0.0015 (5)
C3	0.0295 (7)	0.0423 (10)	0.0217 (7)	0.0034 (7)	0.0127 (6)	−0.0065 (6)
C4	0.0288 (7)	0.0405 (9)	0.0162 (6)	−0.0032 (6)	0.0091 (5)	−0.0045 (6)
C5	0.0209 (6)	0.0346 (8)	0.0129 (6)	−0.0037 (5)	0.0033 (5)	0.0000 (5)
C6	0.0217 (6)	0.0234 (7)	0.0151 (6)	0.0022 (5)	0.0074 (5)	0.0044 (5)
C7	0.0157 (5)	0.0180 (6)	0.0121 (5)	−0.0026 (4)	0.0057 (4)	−0.0007 (4)
C8	0.0158 (5)	0.0166 (6)	0.0151 (5)	−0.0011 (4)	0.0073 (4)	−0.0017 (4)
C9	0.0173 (5)	0.0171 (6)	0.0137 (5)	−0.0029 (4)	0.0064 (4)	−0.0009 (4)
C10	0.0162 (5)	0.0171 (6)	0.0140 (5)	−0.0006 (4)	0.0065 (4)	−0.0001 (4)
C11	0.0181 (6)	0.0174 (6)	0.0163 (6)	−0.0011 (4)	0.0080 (5)	0.0004 (4)
C12	0.0190 (6)	0.0196 (6)	0.0142 (5)	−0.0026 (5)	0.0054 (4)	−0.0012 (4)

O1—C8	1.2541 (16)	C2—H2A	0.9900
N1—C8	1.3437 (17)	C2—H2B	0.9900
N1—C7	1.4670 (16)	C3—C4	1.520 (2)
N1—H1N	0.88 (2)	C3—H3A	0.9900
N2—C10	1.3488 (17)	C3—H3B	0.9900
N2—C7	1.4698 (16)	C4—C5	1.527 (2)
N2—H2N	0.87 (2)	C4—H4A	0.9900
N3—C10	1.3376 (16)	C4—H4B	0.9900
N3—C11	1.3505 (17)	C5—C6	1.529 (2)
N4—C12	1.3215 (17)	C5—H5A	0.9900
N4—C11	1.3552 (17)	C5—H5B	0.9900
N5—C11	1.3328 (17)	C6—C7	1.5304 (18)
N5—H0A	0.87 (2)	C6—H6A	0.9900
N5—H0B	0.84 (2)	C6—H6B	0.9900
C1—C2	1.525 (2)	C8—C9	1.4543 (18)
C1—C7	1.5408 (19)	C9—C12	1.3883 (18)
C1—H1A	0.9900	C9—C10	1.4144 (17)
C1—H1B	0.9900	C12—H12	0.9500
C2—C3	1.531 (2)
C8—N1—C7	123.01 (11)	H4A—C4—H4B	107.4
C8—N1—H1N	118.1 (14)	C4—C5—C6	113.60 (12)
C7—N1—H1N	118.0 (14)	C4—C5—H5A	108.8
C10—N2—C7	119.65 (10)	C6—C5—H5A	108.8
C10—N2—H2N	117.5 (13)	C4—C5—H5B	108.8
C7—N2—H2N	119.5 (13)	C6—C5—H5B	108.8
C10—N3—C11	115.90 (11)	H5A—C5—H5B	107.7
C12—N4—C11	115.27 (11)	C5—C6—C7	116.11 (12)
C11—N5—H0A	120.4 (12)	C5—C6—H6A	108.3
C11—N5—H0B	118.1 (14)	C7—C6—H6A	108.3
H0A—N5—H0B	120.3 (19)	C5—C6—H6B	108.3
C2—C1—C7	115.82 (12)	C7—C6—H6B	108.3
C2—C1—H1A	108.3	H6A—C6—H6B	107.4
C7—C1—H1A	108.3	N1—C7—N2	107.14 (10)
C2—C1—H1B	108.3	N1—C7—C6	108.14 (11)
C7—C1—H1B	108.3	N2—C7—C6	109.00 (10)
H1A—C1—H1B	107.4	N1—C7—C1	110.33 (10)
C1—C2—C3	113.10 (12)	N2—C7—C1	109.07 (11)
C1—C2—H2A	109.0	C6—C7—C1	112.98 (11)
C3—C2—H2A	109.0	O1—C8—N1	121.95 (12)
C1—C2—H2B	109.0	O1—C8—C9	122.43 (12)
C3—C2—H2B	109.0	N1—C8—C9	115.49 (11)
H2A—C2—H2B	107.8	C12—C9—C10	115.88 (12)
C4—C3—C2	115.65 (13)	C12—C9—C8	123.65 (11)
C4—C3—H3A	108.4	C10—C9—C8	119.55 (11)
C2—C3—H3A	108.4	N3—C10—N2	119.12 (11)
C4—C3—H3B	108.4	N3—C10—C9	122.00 (12)
C2—C3—H3B	108.4	N2—C10—C9	118.83 (12)
H3A—C3—H3B	107.4	N5—C11—N3	117.18 (12)
C3—C4—C5	115.99 (13)	N5—C11—N4	115.99 (12)
C3—C4—H4A	108.3	N3—C11—N4	126.82 (12)
C5—C4—H4A	108.3	N4—C12—C9	123.97 (12)
C3—C4—H4B	108.3	N4—C12—H12	118.0
C5—C4—H4B	108.3	C9—C12—H12	118.0
C7—C1—C2—C3	90.57 (16)	O1—C8—C9—C12	5.9 (2)
C1—C2—C3—C4	−67.94 (19)	N1—C8—C9—C12	−178.21 (12)
C2—C3—C4—C5	50.1 (2)	O1—C8—C9—C10	−162.74 (13)
C3—C4—C5—C6	−71.13 (19)	N1—C8—C9—C10	13.19 (18)
C4—C5—C6—C7	88.34 (16)	C11—N3—C10—N2	179.16 (12)
C8—N1—C7—N2	−41.57 (16)	C11—N3—C10—C9	1.64 (19)
C8—N1—C7—C6	−158.93 (12)	C7—N2—C10—N3	162.87 (12)
C8—N1—C7—C1	77.05 (15)	C7—N2—C10—C9	−19.52 (19)
C10—N2—C7—N1	42.90 (16)	C12—C9—C10—N3	−2.94 (19)
C10—N2—C7—C6	159.69 (12)	C8—C9—C10—N3	166.53 (12)
C10—N2—C7—C1	−76.53 (15)	C12—C9—C10—N2	179.53 (12)
C5—C6—C7—N1	−158.50 (11)	C8—C9—C10—N2	−11.01 (19)
C5—C6—C7—N2	85.34 (14)	C10—N3—C11—N5	−178.86 (12)
C5—C6—C7—C1	−36.09 (16)	C10—N3—C11—N4	2.2 (2)
C2—C1—C7—N1	76.85 (14)	C12—N4—C11—N5	176.75 (13)
C2—C1—C7—N2	−165.72 (11)	C12—N4—C11—N3	−4.3 (2)
C2—C1—C7—C6	−44.33 (15)	C11—N4—C12—C9	2.6 (2)
C7—N1—C8—O1	−168.59 (12)	C10—C9—C12—N4	0.7 (2)
C7—N1—C8—C9	15.46 (18)	C8—C9—C12—N4	−168.33 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.88 (2)	2.05 (2)	2.9176 (16)	167 (2)
N2—H2N···O1ii	0.87 (2)	2.30 (2)	3.1587 (16)	168.3 (17)
N5—H0B···O1iii	0.84 (2)	2.22 (2)	2.9234 (17)	141.4 (19)
N5—H0A···N3iv	0.87 (2)	2.11 (2)	2.9826 (18)	172.5 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.88 (2)	2.05 (2)	2.9176 (16)	167 (2)
N2—H2N⋯O1ii	0.87 (2)	2.30 (2)	3.1587 (16)	168.3 (17)
N5—H0B⋯O1iii	0.84 (2)	2.22 (2)	2.9234 (17)	141.4 (19)
N5—H0A⋯N3iv	0.87 (2)	2.11 (2)	2.9826 (18)	172.5 (17)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .