Poly[bis-[8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxyl-ato]cadmium].

The title layered coordination polymer, [Cd(C(14)H(16)N(5)O(3))(2)](n) or [Cd(ppa)(2)](n), where ppa is 8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxyl-ate, was syn-thesized under hydro-thermal conditions. The Cd(II) atom (site symmetry 2) exhibits a distorted cis-CdN(2)O(4) octa-hedral geometry defined by two N-monodentate and two O,O'-bidentate ppa monoanions. The extended two-dimensional structure resulting from the bridging ppa species is a grid lying parallel to (001). An N-H⋯O hydrogen bond helps to establish the crystal packing.

Related literature

For the manganese(II), zinc(II), cobalt(II) and nickel(II) complexes of the ppa anion, see: Huang et al. (2008 ▶); Xu et al. (2009 ▶); Qi et al. (2009 ▶); An & Zhu (2010 ▶). For background on the medicinal uses of pipemidic acid, see: Mizuki et al. (1996 ▶).

Experimental

Crystal data

[Cd(C14H16N5O3)2]

M = 717.04

Monoclinic,

a = 23.565 (3) Å

b = 7.4989 (10) Å

c = 18.719 (3) Å

β = 124.133 (2)°

V = 2738.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.86 mm−1

T = 295 K

0.26 × 0.21 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.801, T max = 0.870

9547 measured reflections

3341 independent reflections

2733 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.082

S = 1.03

3341 reflections

209 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.55 e Å−3

Δρmin = −0.52 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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 I, global. DOI: 10.1107/S1600536810043291/hb5694sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043291/hb5694Isup2.hkl

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

[Cd(C14H16N5O3)2]	F(000) = 1464
Mr = 717.04	Dx = 1.739 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2029 reflections
a = 23.565 (3) Å	θ = 2.6–25.2°
b = 7.4989 (10) Å	µ = 0.86 mm−1
c = 18.719 (3) Å	T = 295 K
β = 124.133 (2)°	Prism, colorless
V = 2738.0 (6) Å3	0.26 × 0.21 × 0.16 mm
Z = 4

Bruker SMART CCD diffractometer	3341 independent reflections
Radiation source: fine-focus sealed tube	2733 reflections with I > 2σ(I)
graphite	Rint = 0.042
ω scans	θmax = 28.1°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −31→31
Tmin = 0.801, Tmax = 0.870	k = −9→9
9547 measured reflections	l = −24→17

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0343P)2 + 1.6146P] where P = (Fo2 + 2Fc2)/3
3341 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.55 e Å−3
1 restraint	Δρmin = −0.52 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
Cd1	0.0000	0.98587 (4)	0.2500	0.02310 (10)
O1	0.08374 (10)	0.5183 (3)	0.41826 (15)	0.0332 (5)
O2	0.04106 (10)	0.7822 (3)	0.35767 (15)	0.0344 (5)
O3	0.11120 (10)	0.9456 (3)	0.28957 (14)	0.0317 (5)
N1	0.26146 (11)	0.5764 (3)	0.43559 (15)	0.0219 (5)
N2	0.33353 (11)	0.7134 (3)	0.40468 (15)	0.0216 (5)
N3	0.29069 (12)	0.9516 (3)	0.29966 (17)	0.0262 (5)
N4	0.40508 (11)	0.8712 (3)	0.38073 (16)	0.0235 (5)
N5	0.49005 (11)	0.7117 (3)	0.33262 (16)	0.0220 (5)
C1	0.08550 (13)	0.6605 (4)	0.38550 (18)	0.0222 (6)
C2	0.14781 (13)	0.6884 (3)	0.38139 (18)	0.0201 (6)
C3	0.15495 (13)	0.8283 (3)	0.33412 (18)	0.0204 (6)
C4	0.21915 (13)	0.8271 (3)	0.34077 (18)	0.0192 (6)
C5	0.23209 (14)	0.9413 (4)	0.29215 (19)	0.0246 (6)
H5A	0.1966	1.0149	0.2518	0.030*
C6	0.34189 (14)	0.8435 (3)	0.36193 (18)	0.0208 (6)
C7	0.27239 (13)	0.7084 (3)	0.39339 (18)	0.0197 (6)
C8	0.20076 (14)	0.5712 (4)	0.42765 (19)	0.0227 (6)
H8A	0.1945	0.4798	0.4562	0.027*
C9	0.31463 (14)	0.4398 (4)	0.48763 (19)	0.0266 (6)
H9A	0.3068	0.3881	0.5289	0.032*
H9B	0.3594	0.4961	0.5197	0.032*
C10	0.3138 (2)	0.2948 (4)	0.4318 (2)	0.0468 (9)
H10A	0.2691	0.2417	0.3985	0.070*
H10B	0.3471	0.2055	0.4676	0.070*
H10C	0.3248	0.3444	0.3937	0.070*
C11	0.46394 (14)	0.7639 (4)	0.4430 (2)	0.0263 (6)
H11A	0.4543	0.7030	0.4808	0.032*
H11B	0.5034	0.8405	0.4781	0.032*
C12	0.47967 (14)	0.6281 (4)	0.39627 (19)	0.0248 (6)
H12A	0.5207	0.5626	0.4383	0.030*
H12B	0.4421	0.5436	0.3667	0.030*
C13	0.41713 (15)	0.9697 (4)	0.3225 (2)	0.0257 (6)
H13A	0.4554	1.0511	0.3553	0.031*
H13B	0.3768	1.0385	0.2815	0.031*
C14	0.43293 (15)	0.8350 (4)	0.2749 (2)	0.0270 (7)
H14A	0.3920	0.7653	0.2366	0.032*
H14B	0.4443	0.8992	0.2395	0.032*
H5N	0.5260 (10)	0.785 (3)	0.3622 (16)	0.021 (8)*

	U11	U22	U33	U12	U13	U23
Cd1	0.01777 (14)	0.02430 (17)	0.02992 (18)	0.000	0.01502 (13)	0.000
O1	0.0289 (11)	0.0292 (12)	0.0461 (14)	−0.0023 (9)	0.0239 (11)	0.0077 (10)
O2	0.0284 (12)	0.0353 (12)	0.0484 (15)	0.0102 (9)	0.0270 (11)	0.0151 (11)
O3	0.0223 (11)	0.0349 (12)	0.0430 (14)	0.0074 (9)	0.0213 (10)	0.0144 (10)
N1	0.0186 (11)	0.0210 (12)	0.0262 (14)	0.0015 (9)	0.0126 (11)	0.0024 (10)
N2	0.0175 (11)	0.0250 (12)	0.0251 (14)	−0.0003 (9)	0.0137 (11)	0.0014 (10)
N3	0.0244 (12)	0.0286 (13)	0.0311 (14)	0.0043 (10)	0.0189 (12)	0.0075 (11)
N4	0.0194 (12)	0.0262 (13)	0.0304 (14)	0.0025 (9)	0.0175 (11)	0.0051 (11)
N5	0.0171 (12)	0.0224 (12)	0.0289 (14)	−0.0009 (9)	0.0144 (11)	−0.0003 (10)
C1	0.0170 (13)	0.0259 (15)	0.0244 (16)	−0.0054 (11)	0.0121 (13)	−0.0030 (12)
C2	0.0199 (13)	0.0201 (13)	0.0233 (15)	−0.0036 (10)	0.0140 (12)	−0.0015 (11)
C3	0.0175 (13)	0.0207 (14)	0.0230 (15)	−0.0011 (11)	0.0113 (12)	−0.0032 (11)
C4	0.0189 (13)	0.0195 (13)	0.0207 (15)	−0.0002 (10)	0.0121 (12)	0.0010 (11)
C5	0.0213 (14)	0.0248 (14)	0.0285 (17)	0.0028 (11)	0.0144 (13)	0.0036 (12)
C6	0.0212 (14)	0.0188 (13)	0.0257 (16)	0.0005 (11)	0.0152 (13)	−0.0016 (11)
C7	0.0185 (13)	0.0200 (14)	0.0207 (15)	−0.0021 (10)	0.0111 (12)	−0.0020 (11)
C8	0.0245 (14)	0.0205 (14)	0.0267 (16)	−0.0036 (11)	0.0166 (13)	−0.0010 (12)
C9	0.0225 (14)	0.0253 (15)	0.0282 (17)	0.0057 (11)	0.0119 (14)	0.0093 (12)
C10	0.059 (2)	0.0329 (19)	0.044 (2)	0.0184 (17)	0.026 (2)	0.0076 (16)
C11	0.0204 (14)	0.0343 (16)	0.0253 (16)	0.0028 (12)	0.0135 (13)	0.0041 (13)
C12	0.0209 (14)	0.0265 (15)	0.0285 (17)	0.0016 (11)	0.0148 (13)	0.0045 (13)
C13	0.0255 (14)	0.0221 (14)	0.0377 (18)	0.0026 (11)	0.0227 (14)	0.0076 (13)
C14	0.0287 (15)	0.0270 (15)	0.0326 (18)	0.0045 (12)	0.0216 (15)	0.0075 (13)

Cd1—O2i	2.268 (2)	C2—C8	1.366 (4)
Cd1—O2	2.268 (2)	C2—C3	1.442 (4)
Cd1—O3i	2.3084 (19)	C3—C4	1.447 (3)
Cd1—O3	2.3084 (19)	C4—C7	1.396 (4)
Cd1—N5ii	2.392 (2)	C4—C5	1.402 (4)
Cd1—N5iii	2.392 (2)	C5—H5A	0.9300
O1—C1	1.243 (3)	C8—H8A	0.9300
O2—C1	1.260 (3)	C9—C10	1.501 (4)
O3—C3	1.252 (3)	C9—H9A	0.9700
N1—C8	1.353 (3)	C9—H9B	0.9700
N1—C7	1.378 (3)	C10—H10A	0.9600
N1—C9	1.483 (3)	C10—H10B	0.9600
N2—C7	1.334 (3)	C10—H10C	0.9600
N2—C6	1.344 (3)	C11—C12	1.518 (4)
N3—C5	1.309 (3)	C11—H11A	0.9700
N3—C6	1.376 (3)	C11—H11B	0.9700
N4—C6	1.340 (3)	C12—H12A	0.9700
N4—C11	1.454 (4)	C12—H12B	0.9700
N4—C13	1.470 (3)	C13—C14	1.524 (4)
N5—C12	1.483 (3)	C13—H13A	0.9700
N5—C14	1.484 (3)	C13—H13B	0.9700
N5—Cd1iv	2.392 (2)	C14—H14A	0.9700
N5—H5N	0.893 (10)	C14—H14B	0.9700
C1—C2	1.527 (3)
O2i—Cd1—O2	95.31 (12)	N4—C6—N2	117.9 (2)
O2i—Cd1—O3i	77.61 (7)	N4—C6—N3	116.6 (2)
O2—Cd1—O3i	92.21 (7)	N2—C6—N3	125.4 (2)
O2i—Cd1—O3	92.21 (7)	N2—C7—N1	117.5 (2)
O2—Cd1—O3	77.61 (7)	N2—C7—C4	123.8 (2)
O3i—Cd1—O3	164.98 (10)	N1—C7—C4	118.6 (2)
O2i—Cd1—N5ii	92.86 (8)	N1—C8—C2	125.8 (3)
O2—Cd1—N5ii	154.65 (8)	N1—C8—H8A	117.1
O3i—Cd1—N5ii	112.99 (8)	C2—C8—H8A	117.1
O3—Cd1—N5ii	78.14 (7)	N1—C9—C10	111.6 (3)
O2i—Cd1—N5iii	154.65 (8)	N1—C9—H9A	109.3
O2—Cd1—N5iii	92.86 (8)	C10—C9—H9A	109.3
O3i—Cd1—N5iii	78.14 (7)	N1—C9—H9B	109.3
O3—Cd1—N5iii	112.99 (8)	C10—C9—H9B	109.3
N5ii—Cd1—N5iii	89.87 (11)	H9A—C9—H9B	108.0
C1—O2—Cd1	134.12 (18)	C9—C10—H10A	109.5
C3—O3—Cd1	131.89 (17)	C9—C10—H10B	109.5
C8—N1—C7	119.0 (2)	H10A—C10—H10B	109.5
C8—N1—C9	120.2 (2)	C9—C10—H10C	109.5
C7—N1—C9	120.8 (2)	H10A—C10—H10C	109.5
C7—N2—C6	115.6 (2)	H10B—C10—H10C	109.5
C5—N3—C6	115.3 (2)	N4—C11—C12	110.0 (2)
C6—N4—C11	123.0 (2)	N4—C11—H11A	109.7
C6—N4—C13	122.1 (2)	C12—C11—H11A	109.7
C11—N4—C13	112.2 (2)	N4—C11—H11B	109.7
C12—N5—C14	110.9 (2)	C12—C11—H11B	109.7
C12—N5—Cd1iv	109.91 (16)	H11A—C11—H11B	108.2
C14—N5—Cd1iv	110.40 (17)	N5—C12—C11	112.5 (2)
C12—N5—H5N	106.7 (19)	N5—C12—H12A	109.1
C14—N5—H5N	103.1 (19)	C11—C12—H12A	109.1
Cd1iv—N5—H5N	115.7 (18)	N5—C12—H12B	109.1
O1—C1—O2	125.1 (2)	C11—C12—H12B	109.1
O1—C1—C2	116.2 (2)	H12A—C12—H12B	107.8
O2—C1—C2	118.7 (2)	N4—C13—C14	108.2 (2)
C8—C2—C3	118.5 (2)	N4—C13—H13A	110.1
C8—C2—C1	116.2 (2)	C14—C13—H13A	110.1
C3—C2—C1	125.2 (2)	N4—C13—H13B	110.1
O3—C3—C2	125.7 (2)	C14—C13—H13B	110.1
O3—C3—C4	119.5 (2)	H13A—C13—H13B	108.4
C2—C3—C4	114.8 (2)	N5—C14—C13	114.0 (2)
C7—C4—C5	114.2 (2)	N5—C14—H14A	108.7
C7—C4—C3	123.2 (2)	C13—C14—H14A	108.7
C5—C4—C3	122.6 (2)	N5—C14—H14B	108.7
N3—C5—C4	124.5 (3)	C13—C14—H14B	108.7
N3—C5—H5A	117.7	H14A—C14—H14B	107.6
C4—C5—H5A	117.7
O2i—Cd1—O2—C1	61.3 (3)	C13—N4—C6—N3	−18.1 (4)
O3i—Cd1—O2—C1	139.0 (3)	C7—N2—C6—N4	170.3 (2)
O3—Cd1—O2—C1	−29.8 (3)	C7—N2—C6—N3	−9.9 (4)
N5ii—Cd1—O2—C1	−47.0 (4)	C5—N3—C6—N4	−169.7 (3)
N5iii—Cd1—O2—C1	−142.7 (3)	C5—N3—C6—N2	10.6 (4)
O2i—Cd1—O3—C3	−80.2 (3)	C6—N2—C7—N1	179.6 (2)
O2—Cd1—O3—C3	14.7 (3)	C6—N2—C7—C4	0.4 (4)
O3i—Cd1—O3—C3	−33.5 (3)	C8—N1—C7—N2	177.9 (2)
N5ii—Cd1—O3—C3	−172.7 (3)	C9—N1—C7—N2	−3.2 (4)
N5iii—Cd1—O3—C3	102.6 (3)	C8—N1—C7—C4	−2.9 (4)
Cd1—O2—C1—O1	−148.5 (2)	C9—N1—C7—C4	176.0 (2)
Cd1—O2—C1—C2	33.1 (4)	C5—C4—C7—N2	7.0 (4)
O1—C1—C2—C8	−11.5 (4)	C3—C4—C7—N2	−175.3 (3)
O2—C1—C2—C8	167.1 (3)	C5—C4—C7—N1	−172.2 (2)
O1—C1—C2—C3	169.4 (3)	C3—C4—C7—N1	5.5 (4)
O2—C1—C2—C3	−12.0 (4)	C7—N1—C8—C2	−0.8 (4)
Cd1—O3—C3—C2	−6.4 (4)	C9—N1—C8—C2	−179.7 (3)
Cd1—O3—C3—C4	173.52 (18)	C3—C2—C8—N1	2.0 (4)
C8—C2—C3—O3	−179.5 (3)	C1—C2—C8—N1	−177.2 (3)
C1—C2—C3—O3	−0.4 (5)	C8—N1—C9—C10	98.4 (3)
C8—C2—C3—C4	0.6 (4)	C7—N1—C9—C10	−80.4 (3)
C1—C2—C3—C4	179.6 (2)	C6—N4—C11—C12	101.2 (3)
O3—C3—C4—C7	175.7 (3)	C13—N4—C11—C12	−60.4 (3)
C2—C3—C4—C7	−4.3 (4)	C14—N5—C12—C11	−50.3 (3)
O3—C3—C4—C5	−6.7 (4)	Cd1iv—N5—C12—C11	−172.71 (18)
C2—C3—C4—C5	173.2 (3)	N4—C11—C12—N5	55.3 (3)
C6—N3—C5—C4	−1.7 (4)	C6—N4—C13—C14	−102.7 (3)
C7—C4—C5—N3	−6.3 (4)	C11—N4—C13—C14	59.0 (3)
C3—C4—C5—N3	176.0 (3)	C12—N5—C14—C13	50.8 (3)
C11—N4—C6—N2	1.9 (4)	Cd1iv—N5—C14—C13	172.90 (17)
C13—N4—C6—N2	161.7 (2)	N4—C13—C14—N5	−54.3 (3)
C11—N4—C6—N3	−177.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···O1v	0.89 (1)	2.10 (1)	2.959 (3)	161 (3)

Table 1

Selected bond lengths (Å)

Cd1—O2	2.268 (2)
Cd1—O3	2.3084 (19)
Cd1—N5i	2.392 (2)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5N⋯O1ii	0.89 (1)	2.10 (1)	2.959 (3)	161 (3)

Symmetry code: (ii) .