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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page m1492
https://doi.org/10.1107/S1600536810043291

Poly[bis­­[8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-di­hydro­pyrido[2,3-d]pyrimidine-6-carboxyl­ato]cadmium]

Jun Gao,a Jing Gao,b Bo Peic and Jing Huangd*

aSchool of Physical Education and Sports Science, Harbin Normal University, Harbin 150025, People's Republic of China, bDepartment of Pharmacy, Mudanjiang Medical University, Mudanjiang 157011, People's Republic of China, cSchool of Chemistry and Chemical Engineering, Harbin Normal University, Harbin 150025, People's Republic of China, and dSchool of Pharmaceutical Science, Harbin Medical University, Harbin 150086, People's Republic of China
*Correspondence e-mail: hj_hmd@sina.com

(Received 20 October 2010; accepted 23 October 2010; online 31 October 2010)

The title layered coordination polymer, [Cd(C14H16N5O3)2]n or [Cd(ppa)2]n, where ppa is 8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydro­pyrido[2,3-d]pyrimidine-6-carboxyl­ate, was syn­thesized under hydro­thermal conditions. The CdII atom (site symmetry 2) exhibits a distorted cis-CdN2O4 octa­hedral 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[Huang, J., Hu, W.-P. & An, Z. (2008). Acta Cryst. E64, m547.]); Xu et al. (2009[Xu, W., Zhu, D.-S., Song, X.-D. & An, Z. (2009). Acta Cryst. E65, m1223.]); Qi et al. (2009[Qi, X., Shao, M. & Li, C.-X. (2009). Acta Cryst. E65, m1334.]); An & Zhu (2010[An, Z. & Zhu, L. (2010). Acta Cryst. E66, m123.]). For background on the medicinal uses of pipemidic acid, see: Mizuki et al. (1996[Mizuki, Y., Fujiwara, I. & Yamaguchi, T. (1996). J. Antimicrob. Chemother. 37 Suppl. A, 41-45.]).

[Scheme 1]

Experimental

Crystal data

  • [Cd(C14H16N5O3)2]

  • Mr = 717.04

  • Monoclinic, C 2/c

  • 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[Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.801, Tmax = 0.870

  • 9547 measured reflections

  • 3341 independent reflections

  • 2733 reflections with I > 2σ(I)

  • Rint = 0.042
Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 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

Table 1
Selected bond lengths (Å)

Cd1—O2 2.268 (2)
Cd1—O3 2.3084 (19)
Cd1—N5i 2.392 (2)
Symmetry code: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

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) [x+{\script{1\over 2}}, y+{\script{1\over 2}}, z].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810043291/hb5694sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810043291/hb5694Isup2.hkl

checkCIF report


Comment top

Pipemidic acid (Hppa, C14H16N5O3, 8-Ethyl-5,8-dihydro-5-oxo-2- (1-piperazinyl)-pyrido(2,3 - d)-pyrimidine-6-carboxylic acid) is member of a class of quinolones used to treat infections (Mizuki et al., 1996). Manganese(II),zinc(II), cobalt(II) and nickel(II) derivatives of ppa have been reported (Huang et al. 2008; Xu et al.2009; Qi et al. 2009; An & Zhu, 2010) The title cadmium(II) complex is reported here(Fig. 1).

The cadmium(II) atom is coordinated by four oxygen atoms and two N atoms from four ppa ligands (two monodentate-N and two O,O-bidentate) to form a square grid propagating in (Fig. 2).

Related literature top

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 top

A mixture of Cd(CH3COO)2.2H2O (0.13 g, 0.5 mmol), Hppa (0.15 g, 0.5 mmol), sodium hydroxide(0.04 g,1 mmol) and water (15 ml) was stirred for 30 min in air. The mixture was then transferred to a 25 ml Teflon-lined hydrothermal bomb. The bomb was kept at 433 K for 72 h under autogenous pressure. Upon cooling, colorless prisms of the title compound were obtained from the reaction mixture.

Refinement top

The carbon-bound H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) = 1.2Ueq(C). The H on Nitrogen atoms were located in a difference Fourier map, and were refined with a distance restraint of N—H = 0.86 (1) /%A and with Uiso(H) = 1.2Ueq(N).

Structure description top

Pipemidic acid (Hppa, C14H16N5O3, 8-Ethyl-5,8-dihydro-5-oxo-2- (1-piperazinyl)-pyrido(2,3 - d)-pyrimidine-6-carboxylic acid) is member of a class of quinolones used to treat infections (Mizuki et al., 1996). Manganese(II),zinc(II), cobalt(II) and nickel(II) derivatives of ppa have been reported (Huang et al. 2008; Xu et al.2009; Qi et al. 2009; An & Zhu, 2010) The title cadmium(II) complex is reported here(Fig. 1).

The cadmium(II) atom is coordinated by four oxygen atoms and two N atoms from four ppa ligands (two monodentate-N and two O,O-bidentate) to form a square grid propagating in (Fig. 2).

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).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound extended to show the cadmium coordination, showing the showing 50% displacement ellipsoids.
[Figure 2] Fig. 2. A view of part of a two-dimensional polymeric sheet in (I) showing the square-grid connectivity (H atoms omitted for clarity).
Poly[bis[8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydropyrido[2,3- d]pyrimidine-6-carboxylato]cadmium(II)] top
Crystal data top
[Cd(C14H16N5O3)2]F(000) = 1464
Mr = 717.04Dx = 1.739 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2029 reflections
a = 23.565 (3) Åθ = 2.6–25.2°
b = 7.4989 (10) ŵ = 0.86 mm−1
c = 18.719 (3) ÅT = 295 K
β = 124.133 (2)°Prism, colorless
V = 2738.0 (6) Å30.26 × 0.21 × 0.16 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer		3341 independent reflections
Radiation source: fine-focus sealed tube2733 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ω scansθmax = 28.1°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −31→31
Tmin = 0.801, Tmax = 0.870k = −9→9
9547 measured reflectionsl = −24→17
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H 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 parametersΔρmax = 0.55 e Å−3
1 restraintΔρmin = −0.52 e Å−3
Crystal data top
[Cd(C14H16N5O3)2]V = 2738.0 (6) Å3
Mr = 717.04Z = 4
Monoclinic, C2/cMo Kα radiation
a = 23.565 (3) ŵ = 0.86 mm−1
b = 7.4989 (10) ÅT = 295 K
c = 18.719 (3) Å0.26 × 0.21 × 0.16 mm
β = 124.133 (2)°
Data collection top
Bruker SMART CCD
diffractometer		3341 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		2733 reflections with I > 2σ(I)
Tmin = 0.801, Tmax = 0.870Rint = 0.042
9547 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0381 restraint
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.55 e Å−3
3341 reflectionsΔρmin = −0.52 e Å−3
209 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cd10.00000.98587 (4)0.25000.02310 (10)
O10.08374 (10)0.5183 (3)0.41826 (15)0.0332 (5)
O20.04106 (10)0.7822 (3)0.35767 (15)0.0344 (5)
O30.11120 (10)0.9456 (3)0.28957 (14)0.0317 (5)
N10.26146 (11)0.5764 (3)0.43559 (15)0.0219 (5)
N20.33353 (11)0.7134 (3)0.40468 (15)0.0216 (5)
N30.29069 (12)0.9516 (3)0.29966 (17)0.0262 (5)
N40.40508 (11)0.8712 (3)0.38073 (16)0.0235 (5)
N50.49005 (11)0.7117 (3)0.33262 (16)0.0220 (5)
C10.08550 (13)0.6605 (4)0.38550 (18)0.0222 (6)
C20.14781 (13)0.6884 (3)0.38139 (18)0.0201 (6)
C30.15495 (13)0.8283 (3)0.33412 (18)0.0204 (6)
C40.21915 (13)0.8271 (3)0.34077 (18)0.0192 (6)
C50.23209 (14)0.9413 (4)0.29215 (19)0.0246 (6)
H5A0.19661.01490.25180.030*
C60.34189 (14)0.8435 (3)0.36193 (18)0.0208 (6)
C70.27239 (13)0.7084 (3)0.39339 (18)0.0197 (6)
C80.20076 (14)0.5712 (4)0.42765 (19)0.0227 (6)
H8A0.19450.47980.45620.027*
C90.31463 (14)0.4398 (4)0.48763 (19)0.0266 (6)
H9A0.30680.38810.52890.032*
H9B0.35940.49610.51970.032*
C100.3138 (2)0.2948 (4)0.4318 (2)0.0468 (9)
H10A0.26910.24170.39850.070*
H10B0.34710.20550.46760.070*
H10C0.32480.34440.39370.070*
C110.46394 (14)0.7639 (4)0.4430 (2)0.0263 (6)
H11A0.45430.70300.48080.032*
H11B0.50340.84050.47810.032*
C120.47967 (14)0.6281 (4)0.39627 (19)0.0248 (6)
H12A0.52070.56260.43830.030*
H12B0.44210.54360.36670.030*
C130.41713 (15)0.9697 (4)0.3225 (2)0.0257 (6)
H13A0.45541.05110.35530.031*
H13B0.37681.03850.28150.031*
C140.43293 (15)0.8350 (4)0.2749 (2)0.0270 (7)
H14A0.39200.76530.23660.032*
H14B0.44430.89920.23950.032*
H5N0.5260 (10)0.785 (3)0.3622 (16)0.021 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.01777 (14)0.02430 (17)0.02992 (18)0.0000.01502 (13)0.000
O10.0289 (11)0.0292 (12)0.0461 (14)−0.0023 (9)0.0239 (11)0.0077 (10)
O20.0284 (12)0.0353 (12)0.0484 (15)0.0102 (9)0.0270 (11)0.0151 (11)
O30.0223 (11)0.0349 (12)0.0430 (14)0.0074 (9)0.0213 (10)0.0144 (10)
N10.0186 (11)0.0210 (12)0.0262 (14)0.0015 (9)0.0126 (11)0.0024 (10)
N20.0175 (11)0.0250 (12)0.0251 (14)−0.0003 (9)0.0137 (11)0.0014 (10)
N30.0244 (12)0.0286 (13)0.0311 (14)0.0043 (10)0.0189 (12)0.0075 (11)
N40.0194 (12)0.0262 (13)0.0304 (14)0.0025 (9)0.0175 (11)0.0051 (11)
N50.0171 (12)0.0224 (12)0.0289 (14)−0.0009 (9)0.0144 (11)−0.0003 (10)
C10.0170 (13)0.0259 (15)0.0244 (16)−0.0054 (11)0.0121 (13)−0.0030 (12)
C20.0199 (13)0.0201 (13)0.0233 (15)−0.0036 (10)0.0140 (12)−0.0015 (11)
C30.0175 (13)0.0207 (14)0.0230 (15)−0.0011 (11)0.0113 (12)−0.0032 (11)
C40.0189 (13)0.0195 (13)0.0207 (15)−0.0002 (10)0.0121 (12)0.0010 (11)
C50.0213 (14)0.0248 (14)0.0285 (17)0.0028 (11)0.0144 (13)0.0036 (12)
C60.0212 (14)0.0188 (13)0.0257 (16)0.0005 (11)0.0152 (13)−0.0016 (11)
C70.0185 (13)0.0200 (14)0.0207 (15)−0.0021 (10)0.0111 (12)−0.0020 (11)
C80.0245 (14)0.0205 (14)0.0267 (16)−0.0036 (11)0.0166 (13)−0.0010 (12)
C90.0225 (14)0.0253 (15)0.0282 (17)0.0057 (11)0.0119 (14)0.0093 (12)
C100.059 (2)0.0329 (19)0.044 (2)0.0184 (17)0.026 (2)0.0076 (16)
C110.0204 (14)0.0343 (16)0.0253 (16)0.0028 (12)0.0135 (13)0.0041 (13)
C120.0209 (14)0.0265 (15)0.0285 (17)0.0016 (11)0.0148 (13)0.0045 (13)
C130.0255 (14)0.0221 (14)0.0377 (18)0.0026 (11)0.0227 (14)0.0076 (13)
C140.0287 (15)0.0270 (15)0.0326 (18)0.0045 (12)0.0216 (15)0.0075 (13)
Geometric parameters (Å, º) top
Cd1—O2i2.268 (2)C2—C81.366 (4)
Cd1—O22.268 (2)C2—C31.442 (4)
Cd1—O3i2.3084 (19)C3—C41.447 (3)
Cd1—O32.3084 (19)C4—C71.396 (4)
Cd1—N5ii2.392 (2)C4—C51.402 (4)
Cd1—N5iii2.392 (2)C5—H5A0.9300
O1—C11.243 (3)C8—H8A0.9300
O2—C11.260 (3)C9—C101.501 (4)
O3—C31.252 (3)C9—H9A0.9700
N1—C81.353 (3)C9—H9B0.9700
N1—C71.378 (3)C10—H10A0.9600
N1—C91.483 (3)C10—H10B0.9600
N2—C71.334 (3)C10—H10C0.9600
N2—C61.344 (3)C11—C121.518 (4)
N3—C51.309 (3)C11—H11A0.9700
N3—C61.376 (3)C11—H11B0.9700
N4—C61.340 (3)C12—H12A0.9700
N4—C111.454 (4)C12—H12B0.9700
N4—C131.470 (3)C13—C141.524 (4)
N5—C121.483 (3)C13—H13A0.9700
N5—C141.484 (3)C13—H13B0.9700
N5—Cd1iv2.392 (2)C14—H14A0.9700
N5—H5N0.893 (10)C14—H14B0.9700
C1—C21.527 (3)
O2i—Cd1—O295.31 (12)N4—C6—N2117.9 (2)
O2i—Cd1—O3i77.61 (7)N4—C6—N3116.6 (2)
O2—Cd1—O3i92.21 (7)N2—C6—N3125.4 (2)
O2i—Cd1—O392.21 (7)N2—C7—N1117.5 (2)
O2—Cd1—O377.61 (7)N2—C7—C4123.8 (2)
O3i—Cd1—O3164.98 (10)N1—C7—C4118.6 (2)
O2i—Cd1—N5ii92.86 (8)N1—C8—C2125.8 (3)
O2—Cd1—N5ii154.65 (8)N1—C8—H8A117.1
O3i—Cd1—N5ii112.99 (8)C2—C8—H8A117.1
O3—Cd1—N5ii78.14 (7)N1—C9—C10111.6 (3)
O2i—Cd1—N5iii154.65 (8)N1—C9—H9A109.3
O2—Cd1—N5iii92.86 (8)C10—C9—H9A109.3
O3i—Cd1—N5iii78.14 (7)N1—C9—H9B109.3
O3—Cd1—N5iii112.99 (8)C10—C9—H9B109.3
N5ii—Cd1—N5iii89.87 (11)H9A—C9—H9B108.0
C1—O2—Cd1134.12 (18)C9—C10—H10A109.5
C3—O3—Cd1131.89 (17)C9—C10—H10B109.5
C8—N1—C7119.0 (2)H10A—C10—H10B109.5
C8—N1—C9120.2 (2)C9—C10—H10C109.5
C7—N1—C9120.8 (2)H10A—C10—H10C109.5
C7—N2—C6115.6 (2)H10B—C10—H10C109.5
C5—N3—C6115.3 (2)N4—C11—C12110.0 (2)
C6—N4—C11123.0 (2)N4—C11—H11A109.7
C6—N4—C13122.1 (2)C12—C11—H11A109.7
C11—N4—C13112.2 (2)N4—C11—H11B109.7
C12—N5—C14110.9 (2)C12—C11—H11B109.7
C12—N5—Cd1iv109.91 (16)H11A—C11—H11B108.2
C14—N5—Cd1iv110.40 (17)N5—C12—C11112.5 (2)
C12—N5—H5N106.7 (19)N5—C12—H12A109.1
C14—N5—H5N103.1 (19)C11—C12—H12A109.1
Cd1iv—N5—H5N115.7 (18)N5—C12—H12B109.1
O1—C1—O2125.1 (2)C11—C12—H12B109.1
O1—C1—C2116.2 (2)H12A—C12—H12B107.8
O2—C1—C2118.7 (2)N4—C13—C14108.2 (2)
C8—C2—C3118.5 (2)N4—C13—H13A110.1
C8—C2—C1116.2 (2)C14—C13—H13A110.1
C3—C2—C1125.2 (2)N4—C13—H13B110.1
O3—C3—C2125.7 (2)C14—C13—H13B110.1
O3—C3—C4119.5 (2)H13A—C13—H13B108.4
C2—C3—C4114.8 (2)N5—C14—C13114.0 (2)
C7—C4—C5114.2 (2)N5—C14—H14A108.7
C7—C4—C3123.2 (2)C13—C14—H14A108.7
C5—C4—C3122.6 (2)N5—C14—H14B108.7
N3—C5—C4124.5 (3)C13—C14—H14B108.7
N3—C5—H5A117.7H14A—C14—H14B107.6
C4—C5—H5A117.7
O2i—Cd1—O2—C161.3 (3)C13—N4—C6—N3−18.1 (4)
O3i—Cd1—O2—C1139.0 (3)C7—N2—C6—N4170.3 (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—N210.6 (4)
O2i—Cd1—O3—C3−80.2 (3)C6—N2—C7—N1179.6 (2)
O2—Cd1—O3—C314.7 (3)C6—N2—C7—C40.4 (4)
O3i—Cd1—O3—C3−33.5 (3)C8—N1—C7—N2177.9 (2)
N5ii—Cd1—O3—C3−172.7 (3)C9—N1—C7—N2−3.2 (4)
N5iii—Cd1—O3—C3102.6 (3)C8—N1—C7—C4−2.9 (4)
Cd1—O2—C1—O1−148.5 (2)C9—N1—C7—C4176.0 (2)
Cd1—O2—C1—C233.1 (4)C5—C4—C7—N27.0 (4)
O1—C1—C2—C8−11.5 (4)C3—C4—C7—N2−175.3 (3)
O2—C1—C2—C8167.1 (3)C5—C4—C7—N1−172.2 (2)
O1—C1—C2—C3169.4 (3)C3—C4—C7—N15.5 (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—C4173.52 (18)C3—C2—C8—N12.0 (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—C1098.4 (3)
C8—C2—C3—C40.6 (4)C7—N1—C9—C10−80.4 (3)
C1—C2—C3—C4179.6 (2)C6—N4—C11—C12101.2 (3)
O3—C3—C4—C7175.7 (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—C5173.2 (3)N4—C11—C12—N555.3 (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—C1459.0 (3)
C3—C4—C5—N3176.0 (3)C12—N5—C14—C1350.8 (3)
C11—N4—C6—N21.9 (4)Cd1iv—N5—C14—C13172.90 (17)
C13—N4—C6—N2161.7 (2)N4—C13—C14—N5−54.3 (3)
C11—N4—C6—N3−177.9 (3)
Symmetry codes: (i) −x, y, −z+1/2; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x−1/2, y+1/2, z; (iv) x+1/2, y−1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5N···O1v0.89 (1)2.10 (1)2.959 (3)161 (3)
Symmetry code: (v) x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula[Cd(C14H16N5O3)2]
Mr717.04
Crystal system, space groupMonoclinic, C2/c
Temperature (K)295
a, b, c (Å)23.565 (3), 7.4989 (10), 18.719 (3)
β (°) 124.133 (2)
V (Å3)2738.0 (6)
Z4
Radiation typeMo Kα
µ (mm−1)0.86
Crystal size (mm)0.26 × 0.21 × 0.16
Data collection
DiffractometerBruker SMART CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.801, 0.870
No. of measured, independent and
observed [I > 2σ(I)] reflections		9547, 3341, 2733
Rint0.042
(sin θ/λ)max (Å−1)0.663
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.082, 1.03
No. of reflections3341
No. of parameters209
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.55, −0.52

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Cd1—O22.268 (2)Cd1—N5i2.392 (2)
Cd1—O32.3084 (19)
Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5N···O1ii0.893 (10)2.101 (13)2.959 (3)161 (3)
Symmetry code: (ii) x+1/2, y+1/2, z.
 

Acknowledgements

The authors thank the Scientific Research Fund of Heilongjiang Provincial Education Department (grant No. 11551281).

References

First citationAn, Z. & Zhu, L. (2010). Acta Cryst. E66, m123.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationBruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationHuang, J., Hu, W.-P. & An, Z. (2008). Acta Cryst. E64, m547.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationMizuki, Y., Fujiwara, I. & Yamaguchi, T. (1996). J. Antimicrob. Chemother. 37 Suppl. A, 41–45.  CrossRef Google Scholar
 First citationQi, X., Shao, M. & Li, C.-X. (2009). Acta Cryst. E65, m1334.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationXu, W., Zhu, D.-S., Song, X.-D. & An, Z. (2009). Acta Cryst. E65, m1223.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page m1492
https://doi.org/10.1107/S1600536810043291
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