Spiro-[cyclo-pentane-1,2'(1'H)-pyrido[2,3-d]pyrimidin]-4'(3'H)-one.

The title compound, C(11)H(13)N(2)O, was obtained by cyclo-condensation of 2-amino-pyridine-3-carbonitrile with cyclo-penta-none. The mol-ecule is built up from two fused six-membered rings and one five-membered ring linked through a spiro C atom. Both the pyrimidine and the cyclo-pentane rings adopt envelope conformations. In the crystal structure, mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds.

Related literature

Many compounds containing the pyrido[2,3-d]pyrimidine scaffold show pharmacological properties such as anti­tumor (Gangjee et al., 1996 ▶), analgesic (Cordeu et al., 2007 ▶) and anti­bacterial (Robins & Hitchings, 1958 ▶) activities. 2-Substituted 2,3-dihydro­pyrido[2,3-d]pyrimidin-4(1H)-one derivatives can be obtained by a Friedlander quinoline condensation, see: Li et al. (2008 ▶). For a related structure, see: Zhang et al. (2008 ▶). For our previous work, see: Li et al. (2009 ▶); Ma et al. (2006 ▶).

Experimental

Crystal data

C11H13N3O

M = 203.24

Orthorhombic,

a = 10.400 (1) Å

b = 12.1650 (15) Å

c = 15.370 (2) Å

V = 1944.6 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 113 K

0.32 × 0.30 × 0.28 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (Crystal Clear-SM Expert; Rigaku/MSC, 2009 ▶) T min = 0.971, T max = 0.974

21571 measured reflections

2314 independent reflections

2168 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.103

S = 1.05

2314 reflections

144 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.20 e Å−3

Data collection: Crystal Clear-SM Expert (Rigaku/MSC, 2009 ▶); cell refinement: Crystal Clear-SM Expert; data reduction: Crystal Clear-SM Expert; 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 datablocks global, I. DOI: 10.1107/S1600536810027479/lx2156sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027479/lx2156Isup2.hkl

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

C11H13N3O	F(000) = 864
Mr = 203.24	Dx = 1.388 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9441 reflections
a = 10.400 (1) Å	θ = 1.3–35.6°
b = 12.1650 (15) Å	µ = 0.09 mm−1
c = 15.370 (2) Å	T = 113 K
V = 1944.6 (4) Å3	Block, colorless
Z = 8	0.32 × 0.30 × 0.28 mm

Rigaku Saturn724 CCD diffractometer	2314 independent reflections
Radiation source: rotating anode	2168 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.037
Detector resolution: 14.222 pixels mm-1	θmax = 27.9°, θmin = 2.7°
ω scans	h = −13→13
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku/MSC, 2009)	k = −16→15
Tmin = 0.971, Tmax = 0.974	l = −20→20
21571 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)] = 0.040	Hydrogen site location: difference Fourier map
wR(F2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0569P)2 + 0.6834P] where P = (Fo2 + 2Fc2)/3
2314 reflections	(Δ/σ)max < 0.001
144 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.20 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	0.59391 (7)	0.42006 (6)	0.57792 (5)	0.01563 (19)
N1	0.94264 (9)	0.63850 (8)	0.68372 (6)	0.0171 (2)
N2	0.80796 (9)	0.69549 (8)	0.57226 (6)	0.0155 (2)
N3	0.64694 (9)	0.58137 (7)	0.51402 (6)	0.0146 (2)
C1	0.84778 (10)	0.61467 (9)	0.62723 (7)	0.0137 (2)
C2	0.78414 (10)	0.51204 (9)	0.62574 (7)	0.0137 (2)
C3	0.82323 (11)	0.43170 (9)	0.68436 (7)	0.0164 (2)
H3	0.7818	0.3621	0.6855	0.020*
C4	0.92347 (11)	0.45420 (9)	0.74123 (7)	0.0185 (2)
H4	0.9539	0.4001	0.7808	0.022*
C5	0.97766 (11)	0.55837 (9)	0.73836 (7)	0.0184 (2)
H5	1.0449	0.5740	0.7783	0.022*
C6	0.66943 (10)	0.49939 (9)	0.57020 (7)	0.0130 (2)
C7	0.74197 (10)	0.66576 (8)	0.49201 (7)	0.0134 (2)
C8	0.83702 (11)	0.62728 (9)	0.42121 (7)	0.0168 (2)
H8A	0.9065	0.5818	0.4465	0.020*
H8B	0.7924	0.5845	0.3755	0.020*
C9	0.88986 (11)	0.73498 (9)	0.38493 (7)	0.0193 (2)
H9A	0.9265	0.7242	0.3261	0.023*
H9B	0.9571	0.7656	0.4235	0.023*
C10	0.77185 (12)	0.81065 (10)	0.38176 (8)	0.0231 (3)
H10A	0.7316	0.8083	0.3234	0.028*
H10B	0.7969	0.8875	0.3947	0.028*
C11	0.67779 (10)	0.76755 (9)	0.45118 (7)	0.0160 (2)
H11A	0.5946	0.7474	0.4242	0.019*
H11B	0.6620	0.8244	0.4960	0.019*
H1	0.8471 (15)	0.7598 (14)	0.5750 (10)	0.030 (4)*
H2	0.5769 (16)	0.5770 (12)	0.4815 (10)	0.024 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0148 (4)	0.0129 (4)	0.0193 (4)	−0.0014 (3)	0.0001 (3)	0.0009 (3)
N1	0.0166 (4)	0.0201 (5)	0.0147 (4)	−0.0014 (4)	−0.0011 (3)	−0.0010 (4)
N2	0.0177 (5)	0.0121 (5)	0.0166 (4)	−0.0029 (4)	−0.0033 (4)	0.0003 (3)
N3	0.0123 (4)	0.0140 (4)	0.0175 (4)	−0.0023 (3)	−0.0029 (4)	0.0020 (3)
C1	0.0134 (5)	0.0147 (5)	0.0131 (5)	0.0007 (4)	0.0024 (4)	−0.0013 (4)
C2	0.0135 (5)	0.0146 (5)	0.0130 (5)	0.0008 (4)	0.0008 (4)	−0.0010 (4)
C3	0.0185 (5)	0.0146 (5)	0.0161 (5)	0.0016 (4)	0.0010 (4)	−0.0001 (4)
C4	0.0201 (5)	0.0205 (5)	0.0147 (5)	0.0049 (4)	−0.0008 (4)	0.0019 (4)
C5	0.0162 (5)	0.0249 (6)	0.0142 (5)	0.0009 (4)	−0.0018 (4)	−0.0007 (4)
C6	0.0130 (5)	0.0121 (5)	0.0139 (5)	0.0016 (4)	0.0021 (4)	−0.0016 (4)
C7	0.0129 (5)	0.0122 (5)	0.0152 (5)	−0.0014 (4)	−0.0008 (4)	0.0011 (4)
C8	0.0179 (5)	0.0153 (5)	0.0171 (5)	0.0017 (4)	0.0006 (4)	0.0003 (4)
C9	0.0182 (5)	0.0191 (6)	0.0206 (5)	0.0000 (4)	0.0036 (4)	0.0028 (4)
C10	0.0252 (6)	0.0196 (6)	0.0246 (6)	0.0040 (5)	0.0057 (5)	0.0082 (5)
C11	0.0147 (5)	0.0138 (5)	0.0195 (5)	0.0010 (4)	−0.0011 (4)	0.0030 (4)

O1—C6	1.2500 (13)	C4—H4	0.9500
N1—C5	1.3372 (14)	C5—H5	0.9500
N1—C1	1.3458 (14)	C7—C11	1.5404 (14)
N2—C1	1.3609 (14)	C7—C8	1.5428 (15)
N2—C7	1.4571 (13)	C8—C9	1.5262 (16)
N2—H1	0.882 (17)	C8—H8A	0.9900
N3—C6	1.3397 (14)	C8—H8B	0.9900
N3—C7	1.4646 (13)	C9—C10	1.5349 (16)
N3—H2	0.885 (16)	C9—H9A	0.9900
C1—C2	1.4132 (15)	C9—H9B	0.9900
C2—C3	1.3900 (15)	C10—C11	1.5397 (15)
C2—C6	1.4750 (14)	C10—H10A	0.9900
C3—C4	1.3878 (16)	C10—H10B	0.9900
C3—H3	0.9500	C11—H11A	0.9900
C4—C5	1.3876 (16)	C11—H11B	0.9900
C5—N1—C1	116.60 (10)	N2—C7—C8	111.75 (9)
C1—N2—C7	119.32 (9)	N3—C7—C8	112.50 (9)
C1—N2—H1	118.1 (10)	C11—C7—C8	103.55 (8)
C7—N2—H1	118.5 (10)	C9—C8—C7	103.17 (9)
C6—N3—C7	123.56 (9)	C9—C8—H8A	111.1
C6—N3—H2	117.6 (9)	C7—C8—H8A	111.1
C7—N3—H2	117.8 (9)	C9—C8—H8B	111.1
N1—C1—N2	117.90 (10)	C7—C8—H8B	111.1
N1—C1—C2	122.96 (10)	H8A—C8—H8B	109.1
N2—C1—C2	119.05 (10)	C8—C9—C10	103.80 (9)
C3—C2—C1	118.28 (10)	C8—C9—H9A	111.0
C3—C2—C6	122.57 (10)	C10—C9—H9A	111.0
C1—C2—C6	118.70 (9)	C8—C9—H9B	111.0
C4—C3—C2	119.29 (10)	C10—C9—H9B	111.0
C4—C3—H3	120.4	H9A—C9—H9B	109.0
C2—C3—H3	120.4	C9—C10—C11	106.36 (9)
C5—C4—C3	117.72 (10)	C9—C10—H10A	110.5
C5—C4—H4	121.1	C11—C10—H10A	110.5
C3—C4—H4	121.1	C9—C10—H10B	110.5
N1—C5—C4	125.11 (10)	C11—C10—H10B	110.5
N1—C5—H5	117.4	H10A—C10—H10B	108.6
C4—C5—H5	117.4	C10—C11—C7	106.30 (9)
O1—C6—N3	121.75 (10)	C10—C11—H11A	110.5
O1—C6—C2	122.26 (10)	C7—C11—H11A	110.5
N3—C6—C2	115.89 (9)	C10—C11—H11B	110.5
N2—C7—N3	107.23 (8)	C7—C11—H11B	110.5
N2—C7—C11	110.45 (9)	H11A—C11—H11B	108.7
N3—C7—C11	111.42 (9)
C5—N1—C1—N2	178.43 (10)	C3—C2—C6—N3	−177.04 (10)
C5—N1—C1—C2	1.72 (16)	C1—C2—C6—N3	10.81 (14)
C7—N2—C1—N1	158.25 (10)	C1—N2—C7—N3	44.94 (13)
C7—N2—C1—C2	−24.91 (15)	C1—N2—C7—C11	166.52 (9)
N1—C1—C2—C3	−1.20 (16)	C1—N2—C7—C8	−78.77 (12)
N2—C1—C2—C3	−177.86 (10)	C6—N3—C7—N2	−40.32 (13)
N1—C1—C2—C6	171.29 (10)	C6—N3—C7—C11	−161.29 (10)
N2—C1—C2—C6	−5.38 (15)	C6—N3—C7—C8	82.94 (12)
C1—C2—C3—C4	−0.71 (16)	N2—C7—C8—C9	−79.95 (10)
C6—C2—C3—C4	−172.89 (10)	N3—C7—C8—C9	159.36 (9)
C2—C3—C4—C5	1.92 (16)	C11—C7—C8—C9	38.94 (10)
C1—N1—C5—C4	−0.39 (17)	C7—C8—C9—C10	−39.83 (11)
C3—C4—C5—N1	−1.43 (17)	C8—C9—C10—C11	25.43 (12)
C7—N3—C6—O1	−169.27 (9)	C9—C10—C11—C7	−1.25 (12)
C7—N3—C6—C2	14.28 (15)	N2—C7—C11—C10	96.69 (10)
C3—C2—C6—O1	6.53 (16)	N3—C7—C11—C10	−144.24 (9)
C1—C2—C6—O1	−165.62 (10)	C8—C7—C11—C10	−23.09 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O1i	0.88 (2)	2.05 (2)	2.918 (1)	170 (2)
N3—H2···O1ii	0.89 (2)	2.00 (2)	2.876 (1)	172 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯O1i	0.88 (2)	2.05 (2)	2.918 (1)	170 (2)
N3—H2⋯O1ii	0.89 (2)	2.00 (2)	2.876 (1)	172 (1)

Symmetry codes: (i) ; (ii) .