Poly[[bis­[μ2-8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydro­pyrido[2,3-d]pyrimidine-6-carboxyl­ato]cobalt(II)] dihydrate]

Qi, X.; Shao, M.; Li, C.-X.

doi:10.1107/S1600536809040185

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page m1334

https://doi.org/10.1107/S1600536809040185

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Poly[[bis[μ₂-8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylato]cobalt(II)] dihydrate]

Xu Qi,^a Ming Shao ^a ^* and Chen-Xin Li ^b

^aThe First Affiliated Hospital, Harbin Medical University, Harbin 150001, People's Republic of China, and ^bThe Department of Health Care Services, Harbin Medical University, Harbin 150086, People's Republic of China
^*Correspondence e-mail: shaom_hmu@126.com

(Received 29 September 2009; accepted 2 October 2009; online 10 October 2009)

The title compound, {[Co(C₁₄H₁₆N₅O₃)₂]·2H₂O}_n or [Co(ppa)₂]·2H₂O}_n, where ppa denotes the 8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate anion, was synthesized under hydrothermal conditions. The Co^II atom (site symmetry $[\overline{1}]$ ) exhibits a distorted trans-CoN₂O₄ octahedral geometry defined by two monodentate N-bonded and two bidentate O,O′-bonded ppa anions. The extended two-dimensional structure is a square grid, which is consolidated by N—H⋯O hydrogen bonds. The disordered uncoordinated water molecules occupy cavities within the grid.

Related literature

For the manganese and zinc complexes of the ppa anion, see: Huang et al. (2008 ); Xu et al. (2009 ). For background to the medicinal uses of pipemidic acid, see: Mizuki et al. (1996 ).

Experimental

Crystal data

[Co(C₁₄H₁₆N₅O₃)₂]·2H₂O
M_r = 699.58
Monoclinic, P 2₁ /c
a = 6.1093 (3) Å
b = 21.3690 (11) Å
c = 12.5944 (6) Å
β = 101.254 (1)°
V = 1612.58 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.60 mm⁻¹
T = 295 K
0.32 × 0.26 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.832, T_max = 0.900
9807 measured reflections
3894 independent reflections
3327 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.181
S = 1.12
3894 reflections
227 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.77 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—O3	2.022 (2)
Co1—O1	2.0829 (18)
Co1—N5ⁱ	2.265 (2)
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5N⋯O2ⁱⁱ	0.900 (10)	2.278 (14)	3.156 (4)	165 (3)
Symmetry code: (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809040185/hb5124sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809040185/hb5124Isup2.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). The manganese and cobalt complexes of the ppa anion have been reported (Huang et al., 2008; Xu et al. 2009). The title cobalt(II) complex is reported here(Fig. 1).

The cobalt(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). The disordered, uncoordinated, water molecules occupy the cavities.

Related literature top

For the manganese and zinc complexe of the ppa anion, see: Huang et al. (2008); Xu et al. (2009). For background to the medicinal uses of pipemidic acid, see: Mizuki et al. (1996).

Experimental top

A mixture of Co(CH₃COO)₂.4H₂O (0.25 mmol), Hppa (0.5 mmol), sodium hydroxide (1 mmol) and water (12 ml) was stirred for 40 min in air. The mixture was then transferred to a 23 ml Teflon-lined hydrothermal bomb. The bomb was kept at 433 K for 96 h under autogenous pressure. Upon cooling, pink prisms of (I) were obtained from the reaction mixture.

Structure description top

For the manganese and zinc complexe of the ppa anion, see: Huang et al. (2008); Xu et al. (2009). For background to the medicinal uses of pipemidic acid, see: Mizuki et al. (1996).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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

	Fig. 1. The asymmetric unit of (I) expanded to show the metal coordination and polymeric connectivity showing 50% displacement ellipsoids (water molecule O atoms have been omitted for clarity).
	Fig. 2. A view of part of a two-dimensional polymeric sheet in (I) showing the square-grid connectivity (H atoms and water molecule O atoms omitted for clarity).

Poly[[bis[µ₂-8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8- dihydropyrido[2,3-d]pyrimidine-6-carboxylato]cobalt(II)] dihydrate] top

Crystal data top

[Co(C₁₄H₁₆N₅O₃)₂]·2H₂O	F(000) = 722
M_r = 699.58	D_x = 1.433 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4362 reflections
a = 6.1093 (3) Å	θ = 2.5–28.2°
b = 21.3690 (11) Å	µ = 0.60 mm⁻¹
c = 12.5944 (6) Å	T = 295 K
β = 101.254 (1)°	Prism, pink
V = 1612.58 (14) Å³	0.32 × 0.26 × 0.18 mm
Z = 2

Data collection top

Bruker SMART CCD diffractometer	3894 independent reflections
Radiation source: fine-focus sealed tube	3327 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω scans	θ_max = 28.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→6
T_min = 0.832, T_max = 0.900	k = −27→28
9807 measured reflections	l = −15→15

Refinement top

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.181	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ²(F_o²) + (0.0899P)² + 1.3252P] where P = (F_o² + 2F_c²)/3
3894 reflections	(Δ/σ)_max = 0.003
227 parameters	Δρ_max = 0.77 e Å⁻³
1 restraint	Δρ_min = −0.46 e Å⁻³

Crystal data top

[Co(C₁₄H₁₆N₅O₃)₂]·2H₂O	V = 1612.58 (14) Å³
M_r = 699.58	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.1093 (3) Å	µ = 0.60 mm⁻¹
b = 21.3690 (11) Å	T = 295 K
c = 12.5944 (6) Å	0.32 × 0.26 × 0.18 mm
β = 101.254 (1)°

Data collection top

Bruker SMART CCD diffractometer	3894 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3327 reflections with I > 2σ(I)
T_min = 0.832, T_max = 0.900	R_int = 0.029
9807 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	1 restraint
wR(F²) = 0.181	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.77 e Å⁻³
3894 reflections	Δρ_min = −0.46 e Å⁻³
227 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1W	0.669 (4)	0.5177 (8)	0.5335 (9)	0.255 (11)	0.50
O2W	−0.024 (4)	0.5581 (10)	0.4291 (11)	0.254 (10)	0.50
Co1	0.5000	0.5000	0.0000	0.02469 (18)
O1	0.6496 (3)	0.57810 (9)	0.08289 (16)	0.0324 (4)
O2	0.1437 (5)	0.51651 (14)	0.2499 (2)	0.0626 (8)
N1	0.5101 (5)	0.67072 (13)	0.3478 (2)	0.0487 (7)
N2	0.7758 (5)	0.74617 (12)	0.3332 (2)	0.0390 (6)
N3	1.0138 (5)	0.73519 (13)	0.2023 (2)	0.0437 (7)
N4	1.0250 (4)	0.82327 (11)	0.3106 (2)	0.0362 (6)
C1	0.2840 (5)	0.52788 (13)	0.1939 (2)	0.0328 (6)
C2	0.4347 (5)	0.58348 (13)	0.2241 (2)	0.0330 (6)
C3	0.6059 (4)	0.60347 (12)	0.1662 (2)	0.0275 (5)
C4	0.7269 (5)	0.65898 (13)	0.2104 (2)	0.0318 (6)
C5	0.9081 (5)	0.68298 (14)	0.1695 (3)	0.0398 (7)
H5	0.9566	0.6603	0.1155	0.048*
C6	0.9339 (5)	0.76685 (13)	0.2815 (2)	0.0334 (6)
C7	0.6763 (5)	0.69244 (13)	0.2976 (3)	0.0364 (6)
C8	0.3996 (6)	0.61779 (15)	0.3104 (3)	0.0452 (8)
H8	0.2905	0.6036	0.3467	0.054*
C9	0.4470 (8)	0.7043 (2)	0.4423 (4)	0.0646 (12)
H9A	0.4693	0.7489	0.4351	0.078*
H9B	0.2902	0.6972	0.4425	0.078*
C10	0.5781 (12)	0.6828 (4)	0.5417 (5)	0.118 (2)
H10A	0.5474	0.6393	0.5513	0.177*
H10B	0.5417	0.7065	0.6006	0.177*
H10C	0.7335	0.6880	0.5401	0.177*
C11	1.1614 (6)	0.85706 (17)	0.2461 (3)	0.0478 (8)
H11A	1.0667	0.8839	0.1943	0.057*
H11B	1.2345	0.8274	0.2062	0.057*
C12	1.3372 (5)	0.89675 (15)	0.3196 (3)	0.0400 (7)
H12A	1.4448	0.8690	0.3630	0.048*
H12B	1.4162	0.9216	0.2747	0.048*
C13	1.1106 (5)	0.90153 (13)	0.4537 (2)	0.0330 (6)
H13A	1.0424	0.9293	0.4989	0.040*
H13B	1.2078	0.8731	0.5011	0.040*
C14	0.9295 (5)	0.86418 (14)	0.3823 (3)	0.0353 (6)
H14A	0.8505	0.8392	0.4270	0.042*
H14B	0.8233	0.8925	0.3395	0.042*
N5	1.2458 (4)	0.93890 (10)	0.39246 (19)	0.0286 (5)
O3	0.3027 (3)	0.49641 (8)	0.11147 (17)	0.0295 (4)
H5N	1.155 (5)	0.9660 (14)	0.350 (2)	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1W	0.52 (4)	0.180 (13)	0.073 (8)	−0.084 (17)	0.063 (13)	0.045 (8)
O2W	0.35 (2)	0.33 (2)	0.122 (10)	−0.09 (2)	0.147 (13)	−0.030 (13)
Co1	0.0276 (3)	0.0158 (3)	0.0304 (3)	−0.00028 (17)	0.0050 (2)	−0.00242 (17)
O1	0.0350 (10)	0.0243 (9)	0.0395 (11)	−0.0065 (8)	0.0113 (8)	−0.0089 (8)
O2	0.0732 (18)	0.0635 (16)	0.0631 (17)	−0.0401 (15)	0.0429 (15)	−0.0297 (14)
N1	0.0630 (18)	0.0404 (15)	0.0494 (16)	−0.0222 (14)	0.0271 (14)	−0.0189 (12)
N2	0.0494 (15)	0.0296 (12)	0.0413 (14)	−0.0138 (11)	0.0167 (11)	−0.0129 (10)
N3	0.0454 (15)	0.0348 (14)	0.0556 (16)	−0.0152 (12)	0.0221 (13)	−0.0200 (12)
N4	0.0390 (13)	0.0268 (12)	0.0462 (14)	−0.0093 (10)	0.0169 (11)	−0.0132 (10)
C1	0.0354 (14)	0.0250 (13)	0.0379 (15)	−0.0061 (11)	0.0068 (12)	−0.0030 (11)
C2	0.0409 (15)	0.0244 (13)	0.0343 (14)	−0.0074 (11)	0.0091 (12)	−0.0035 (10)
C3	0.0309 (13)	0.0192 (12)	0.0314 (13)	−0.0023 (10)	0.0034 (10)	−0.0024 (10)
C4	0.0354 (14)	0.0241 (12)	0.0365 (14)	−0.0064 (11)	0.0082 (11)	−0.0064 (11)
C5	0.0434 (16)	0.0300 (14)	0.0498 (18)	−0.0102 (12)	0.0186 (14)	−0.0180 (13)
C6	0.0338 (14)	0.0248 (13)	0.0427 (16)	−0.0058 (11)	0.0097 (12)	−0.0087 (11)
C7	0.0449 (16)	0.0269 (13)	0.0397 (15)	−0.0099 (12)	0.0139 (13)	−0.0087 (11)
C8	0.057 (2)	0.0352 (16)	0.0486 (18)	−0.0198 (15)	0.0238 (16)	−0.0107 (14)
C9	0.080 (3)	0.058 (2)	0.065 (3)	−0.030 (2)	0.035 (2)	−0.025 (2)
C10	0.121 (5)	0.155 (7)	0.082 (4)	−0.025 (5)	0.028 (4)	−0.020 (4)
C11	0.055 (2)	0.0429 (18)	0.0501 (19)	−0.0253 (15)	0.0221 (16)	−0.0187 (15)
C12	0.0370 (15)	0.0326 (15)	0.0537 (18)	−0.0113 (12)	0.0167 (13)	−0.0110 (13)
C13	0.0334 (14)	0.0266 (13)	0.0402 (15)	−0.0067 (11)	0.0104 (12)	−0.0072 (11)
C14	0.0290 (13)	0.0276 (13)	0.0507 (17)	−0.0062 (11)	0.0114 (12)	−0.0119 (12)
N5	0.0283 (11)	0.0208 (10)	0.0362 (12)	−0.0017 (8)	0.0053 (9)	−0.0010 (9)
O3	0.0337 (10)	0.0199 (9)	0.0353 (11)	−0.0035 (7)	0.0072 (8)	−0.0029 (7)

Geometric parameters (Å, º) top

Co1—O3ⁱ	2.022 (2)	C4—C5	1.405 (4)
Co1—O3	2.022 (2)	C5—H5	0.9300
Co1—O1ⁱ	2.0829 (18)	C8—H8	0.9300
Co1—O1	2.0829 (18)	C9—C10	1.425 (9)
Co1—N5ⁱⁱ	2.265 (2)	C9—H9A	0.9700
Co1—N5ⁱⁱⁱ	2.265 (2)	C9—H9B	0.9700
O1—C3	1.255 (3)	C10—H10A	0.9600
O2—C1	1.235 (4)	C10—H10B	0.9600
N1—C8	1.354 (4)	C10—H10C	0.9600
N1—C7	1.376 (4)	C11—C12	1.530 (4)
N1—C9	1.503 (5)	C11—H11A	0.9700
N2—C7	1.335 (4)	C11—H11B	0.9700
N2—C6	1.341 (4)	C12—N5	1.471 (4)
N3—C5	1.315 (4)	C12—H12A	0.9700
N3—C6	1.371 (4)	C12—H12B	0.9700
N4—C6	1.348 (3)	C13—N5	1.471 (3)
N4—C14	1.459 (3)	C13—C14	1.510 (4)
N4—C11	1.462 (4)	C13—H13A	0.9700
C1—O3	1.261 (3)	C13—H13B	0.9700
C1—C2	1.506 (4)	C14—H14A	0.9700
C2—C8	1.362 (4)	C14—H14B	0.9700
C2—C3	1.451 (4)	N5—Co1^iv	2.265 (2)
C3—C4	1.450 (4)	N5—H5N	0.900 (10)
C4—C7	1.396 (4)

O3ⁱ—Co1—O3	180.0	N1—C8—H8	117.2
O3ⁱ—Co1—O1ⁱ	86.86 (7)	C2—C8—H8	117.2
O3—Co1—O1ⁱ	93.14 (7)	C10—C9—N1	110.8 (5)
O3ⁱ—Co1—O1	93.14 (7)	C10—C9—H9A	109.5
O3—Co1—O1	86.86 (7)	N1—C9—H9A	109.5
O1ⁱ—Co1—O1	180.0	C10—C9—H9B	109.5
O3ⁱ—Co1—N5ⁱⁱ	90.28 (8)	N1—C9—H9B	109.5
O3—Co1—N5ⁱⁱ	89.72 (8)	H9A—C9—H9B	108.1
O1ⁱ—Co1—N5ⁱⁱ	91.18 (8)	C9—C10—H10A	109.5
O1—Co1—N5ⁱⁱ	88.82 (8)	C9—C10—H10B	109.5
O3ⁱ—Co1—N5ⁱⁱⁱ	89.72 (8)	H10A—C10—H10B	109.5
O3—Co1—N5ⁱⁱⁱ	90.28 (8)	C9—C10—H10C	109.5
O1ⁱ—Co1—N5ⁱⁱⁱ	88.82 (8)	H10A—C10—H10C	109.5
O1—Co1—N5ⁱⁱⁱ	91.18 (8)	H10B—C10—H10C	109.5
N5ⁱⁱ—Co1—N5ⁱⁱⁱ	180.0	N4—C11—C12	110.3 (3)
C3—O1—Co1	128.37 (17)	N4—C11—H11A	109.6
C8—N1—C7	119.0 (3)	C12—C11—H11A	109.6
C8—N1—C9	119.1 (3)	N4—C11—H11B	109.6
C7—N1—C9	121.9 (3)	C12—C11—H11B	109.6
C7—N2—C6	116.4 (2)	H11A—C11—H11B	108.1
C5—N3—C6	115.1 (3)	N5—C12—C11	114.2 (3)
C6—N4—C14	120.7 (2)	N5—C12—H12A	108.7
C6—N4—C11	122.7 (2)	C11—C12—H12A	108.7
C14—N4—C11	112.8 (2)	N5—C12—H12B	108.7
O2—C1—O3	123.3 (3)	C11—C12—H12B	108.7
O2—C1—C2	118.0 (3)	H12A—C12—H12B	107.6
O3—C1—C2	118.6 (2)	N5—C13—C14	113.3 (2)
C8—C2—C3	118.9 (3)	N5—C13—H13A	108.9
C8—C2—C1	116.3 (3)	C14—C13—H13A	108.9
C3—C2—C1	124.8 (2)	N5—C13—H13B	108.9
O1—C3—C4	119.9 (2)	C14—C13—H13B	108.9
O1—C3—C2	125.8 (2)	H13A—C13—H13B	107.7
C4—C3—C2	114.3 (2)	N4—C14—C13	110.5 (2)
C7—C4—C5	114.4 (2)	N4—C14—H14A	109.5
C7—C4—C3	123.1 (3)	C13—C14—H14A	109.5
C5—C4—C3	122.5 (3)	N4—C14—H14B	109.5
N3—C5—C4	124.7 (3)	C13—C14—H14B	109.5
N3—C5—H5	117.7	H14A—C14—H14B	108.1
C4—C5—H5	117.7	C13—N5—C12	108.4 (2)
N2—C6—N4	117.5 (2)	C13—N5—Co1^iv	112.89 (17)
N2—C6—N3	125.7 (3)	C12—N5—Co1^iv	115.23 (17)
N4—C6—N3	116.9 (3)	C13—N5—H5N	108 (2)
N2—C7—N1	117.7 (3)	C12—N5—H5N	107 (2)
N2—C7—C4	123.3 (3)	Co1^iv—N5—H5N	105 (2)
N1—C7—C4	119.0 (3)	C1—O3—Co1	135.54 (18)
N1—C8—C2	125.6 (3)

O3ⁱ—Co1—O1—C3	−179.8 (2)	C8—N1—C7—N2	177.2 (3)
O3—Co1—O1—C3	0.2 (2)	C9—N1—C7—N2	−2.4 (5)
N5ⁱⁱ—Co1—O1—C3	−89.6 (2)	C8—N1—C7—C4	−0.5 (5)
N5ⁱⁱⁱ—Co1—O1—C3	90.4 (2)	C9—N1—C7—C4	179.9 (4)
O2—C1—C2—C8	−1.4 (5)	C5—C4—C7—N2	6.3 (5)
O3—C1—C2—C8	176.6 (3)	C3—C4—C7—N2	−174.7 (3)
O2—C1—C2—C3	−179.3 (3)	C5—C4—C7—N1	−176.2 (3)
O3—C1—C2—C3	−1.3 (4)	C3—C4—C7—N1	2.8 (5)
Co1—O1—C3—C4	−178.49 (19)	C7—N1—C8—C2	−1.4 (6)
Co1—O1—C3—C2	−0.6 (4)	C9—N1—C8—C2	178.2 (4)
C8—C2—C3—O1	−176.7 (3)	C3—C2—C8—N1	0.9 (6)
C1—C2—C3—O1	1.2 (5)	C1—C2—C8—N1	−177.2 (3)
C8—C2—C3—C4	1.3 (4)	C8—N1—C9—C10	91.4 (5)
C1—C2—C3—C4	179.2 (3)	C7—N1—C9—C10	−89.0 (5)
O1—C3—C4—C7	175.0 (3)	C6—N4—C11—C12	−149.0 (3)
C2—C3—C4—C7	−3.1 (4)	C14—N4—C11—C12	52.8 (4)
O1—C3—C4—C5	−6.0 (4)	N4—C11—C12—N5	−53.2 (4)
C2—C3—C4—C5	175.8 (3)	C6—N4—C14—C13	146.4 (3)
C6—N3—C5—C4	−0.5 (5)	C11—N4—C14—C13	−54.9 (4)
C7—C4—C5—N3	−5.4 (5)	N5—C13—C14—N4	56.7 (3)
C3—C4—C5—N3	175.5 (3)	C14—C13—N5—C12	−55.3 (3)
C7—N2—C6—N4	175.2 (3)	C14—C13—N5—Co1^iv	175.84 (18)
C7—N2—C6—N3	−5.8 (5)	C11—C12—N5—C13	53.7 (4)
C14—N4—C6—N2	−9.8 (4)	C11—C12—N5—Co1^iv	−178.7 (2)
C11—N4—C6—N2	−166.4 (3)	O2—C1—O3—Co1	178.9 (3)
C14—N4—C6—N3	171.1 (3)	C2—C1—O3—Co1	1.0 (4)
C11—N4—C6—N3	14.5 (5)	O1ⁱ—Co1—O3—C1	179.6 (3)
C5—N3—C6—N2	6.6 (5)	O1—Co1—O3—C1	−0.4 (3)
C5—N3—C6—N4	−174.4 (3)	N5ⁱⁱ—Co1—O3—C1	88.4 (3)
C6—N2—C7—N1	−178.7 (3)	N5ⁱⁱⁱ—Co1—O3—C1	−91.6 (3)
C6—N2—C7—C4	−1.1 (5)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, y−1/2, −z+1/2; (iii) x−1, −y+3/2, z−1/2; (iv) −x+2, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···O2^v	0.90 (1)	2.28 (1)	3.156 (4)	165 (3)

Symmetry code: (v) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Co(C₁₄H₁₆N₅O₃)₂]·2H₂O
M_r	699.58
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	6.1093 (3), 21.3690 (11), 12.5944 (6)
β (°)	101.254 (1)
V (Å³)	1612.58 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.60
Crystal size (mm)	0.32 × 0.26 × 0.18

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.832, 0.900
No. of measured, independent and observed [I > 2σ(I)] reflections	9807, 3894, 3327
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.181, 1.12
No. of reflections	3894
No. of parameters	227
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.77, −0.46

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Co1—O3	2.022 (2)	Co1—N5ⁱ	2.265 (2)
Co1—O1	2.0829 (18)

Symmetry code: (i) −x+2, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···O2ⁱⁱ	0.900 (10)	2.278 (14)	3.156 (4)	165 (3)

Symmetry code: (ii) −x+1, y+1/2, −z+1/2.

Acknowledgements

The authors acknowledge financial support from the Foundation for Youth of Heilongjiang Province (grant No. QC07C97).

References

Bruker (1998). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Huang, J., Hu, W.-P. & An, Z. (2008). Acta Cryst. E64, m547. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mizuki, Y., Fujiwara, I. & Yamaguchi, T. (1996). J. Antimicrob. Chemother. 37 (Suppl. A), 41-45. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, W., Zhu, D.-S., Song, X.-D. & An, Z. (2009). Acta Cryst. E65, m1223. Web of Science CSD CrossRef IUCr Journals Google Scholar

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