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

Xu, W.; Zhu, D.-S.; Song, X.-D.; An, Z.

doi:10.1107/S1600536809036939

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page m1223

doi:10.1107/S1600536809036939

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

Wen Xu,^a Da-Sheng Zhu,^a Xiao-Dan Song ^b and Zhe An ^b ^*

^aSecond Hospital, Jilin University, Changchun 130041, People's Republic of China, and ^bSchool of Pharmaceutical Science, Harbin Medical University, Harbin, 150086, People's Republic of China
^*Correspondence e-mail: anzhe6409@sina.com

(Received 22 August 2009; accepted 12 September 2009; online 19 September 2009)

The title compound, {[Zn(C₁₄H₁₆N₅O₃)₂]·2H₂O}_n or [Zn(ppa)₂]·2H₂O}_n, where ppa = 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)-pyrido(2,3-d)-pyrimidine-6-carboxylate, was synthesized under hydrothermal conditions. The Zn^II atom (site symmetry $[\overline{1}]$ ) exhibits a distorted trans-ZnN₂O₄ octahedral geometry defined by two monodentate N-bonded and two bidentate O,O-bonded ppa monoanions. The extended two-dimensional structure arising from this connectivity is a square grid and the disordered uncoordinated water molecules occupy cavities within the grid. An N—H⋯O hydrogen bond occurs.

Related literature

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

Experimental

Crystal data

[Zn(C₁₄H₁₆N₅O₃)₂]·2H₂O
M_r = 704.05
Monoclinic, P 2₁ /c
a = 6.1146 (12) Å
b = 21.424 (4) Å
c = 12.577 (3) Å
β = 101.10 (3)°
V = 1616.9 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.82 mm⁻¹
T = 295 K
0.36 × 0.28 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (CrystalStructure; Rigaku/MSC, 2002 ) T_min = 0.756, T_max = 0.866
15697 measured reflections
3684 independent reflections
2570 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.210
S = 1.06
3684 reflections
228 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.83 e Å⁻³
Δρ_min = −0.83 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O1	2.031 (3)
Zn1—O3	2.107 (2)
Zn1—N5ⁱ	2.275 (3)
Symmetry code: (i) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5N⋯O2ⁱⁱ	0.91 (5)	2.28 (5)	3.168 (5)	166 (4)
Symmetry code: (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809036939/hb5062sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809036939/hb5062Isup2.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 complex of the ppa anion has been reported (Huang et al., 2008); the title zinc(II) complex is reported here (Fig. 1).

The zinc(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 (Fig. 2). The disordered, uncoordinated, water molecules occupy the cavities.

Related literature top

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

Experimental top

A mixture of Zn(CH₃COO)₂.2H₂O (0.055 g, 0.25 mmol), Hppa (0.15 g, 0.5 mmol), sodium hydroxide (0.04 g, 1 mmol) and water (12 ml) was stirred for 30 min in air. The mixture was then transferred to a 23 ml Teflon-lined hydrothermal bomb. The bomb was kept at 433 K for 72 h under autogenous pressure. Upon cooling, colourless prisms of (I) were obtained from the reaction mixture.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku , 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of (I) extended to show the zinc coordination sphere showing the 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]zinc(II)] dihydrate] top

Crystal data top

[Zn(C₁₄H₁₆N₅O₃)₂]·2H₂O	Z = 2
M_r = 704.05	F(000) = 728
Monoclinic, P2₁/c	D_x = 1.442 Mg m⁻³
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 6.1146 (12) Å	µ = 0.82 mm⁻¹
b = 21.424 (4) Å	T = 295 K
c = 12.577 (3) Å	Prism, colorless
β = 101.10 (3)°	0.36 × 0.28 × 0.18 mm
V = 1616.9 (6) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	3684 independent reflections
Radiation source: fine-focus sealed tube	2570 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Detector resolution: 10.000 pixels mm^-1	θ_max = 27.5°, θ_min = 3.3°
ω scans	h = −7→7
Absorption correction: multi-scan (CrystalStructure; Rigaku/MSC, 2002)	k = −27→25
T_min = 0.756, T_max = 0.866	l = −16→16
15697 measured reflections

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.210	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.1254P)² + 1.7801P] where P = (F_o² + 2F_c²)/3
3684 reflections	(Δ/σ)_max < 0.001
228 parameters	Δρ_max = 0.83 e Å⁻³
1 restraint	Δρ_min = −0.83 e Å⁻³

Crystal data top

[Zn(C₁₄H₁₆N₅O₃)₂]·2H₂O	V = 1616.9 (6) Å³
M_r = 704.05	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.1146 (12) Å	µ = 0.82 mm⁻¹
b = 21.424 (4) Å	T = 295 K
c = 12.577 (3) Å	0.36 × 0.28 × 0.18 mm
β = 101.10 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3684 independent reflections
Absorption correction: multi-scan (CrystalStructure; Rigaku/MSC, 2002)	2570 reflections with I > 2σ(I)
T_min = 0.756, T_max = 0.866	R_int = 0.045
15697 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	1 restraint
wR(F²) = 0.210	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.83 e Å⁻³
3684 reflections	Δρ_min = −0.83 e Å⁻³
228 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	−0.045 (3)	−0.0632 (10)	−0.0746 (11)	0.187 (8)	0.50
O2W	0.340 (5)	0.0205 (10)	−0.0364 (12)	0.251 (14)	0.50
Zn1	0.5000	0.0000	0.5000	0.0265 (2)
O1	0.6981 (4)	−0.00325 (10)	0.3877 (2)	0.0271 (6)
O2	0.8573 (7)	0.01818 (18)	0.2500 (3)	0.0616 (11)
O3	0.3495 (5)	0.07935 (11)	0.4179 (2)	0.0317 (6)
N1	0.4916 (7)	0.17173 (17)	0.1532 (3)	0.0481 (10)
N2	0.2252 (6)	0.24690 (15)	0.1677 (3)	0.0386 (8)
N3	−0.0127 (6)	0.23572 (16)	0.2988 (3)	0.0436 (9)
N4	−0.0227 (6)	0.32384 (15)	0.1907 (3)	0.0349 (8)
N5	−0.2450 (5)	0.43908 (14)	0.1084 (2)	0.0273 (7)
H5N	−0.154 (8)	0.466 (2)	0.152 (4)	0.065 (16)*
C1	0.7147 (7)	0.02891 (17)	0.3064 (3)	0.0316 (8)
C2	0.5658 (7)	0.08450 (17)	0.2772 (3)	0.0317 (8)
C3	0.3947 (6)	0.10453 (16)	0.3346 (3)	0.0271 (7)
C4	0.2744 (7)	0.15974 (16)	0.2910 (3)	0.0303 (8)
C5	0.0937 (8)	0.18359 (19)	0.3318 (3)	0.0398 (10)
H5	0.0454	0.1610	0.3861	0.048*
C6	0.0671 (7)	0.26762 (18)	0.2197 (3)	0.0327 (8)
C7	0.3246 (7)	0.19340 (18)	0.2034 (3)	0.0360 (9)
C8	0.6010 (8)	0.1189 (2)	0.1902 (4)	0.0457 (11)
H8	0.7096	0.1047	0.1535	0.055*
C9	0.5540 (11)	0.2051 (3)	0.0585 (5)	0.0665 (16)
H9B	0.5306	0.2496	0.0653	0.080*
H9A	0.7107	0.1983	0.0582	0.080*
C10	0.4247 (16)	0.1834 (5)	−0.0401 (7)	0.116 (3)
H10C	0.4566	0.1401	−0.0496	0.174*
H10B	0.4605	0.2071	−0.0993	0.174*
H10A	0.2693	0.1883	−0.0385	0.174*
C11	−0.1608 (8)	0.3572 (2)	0.2553 (4)	0.0475 (11)
H11B	−0.0673	0.3839	0.3077	0.057*
H11A	−0.2346	0.3275	0.2947	0.057*
C12	−0.3356 (7)	0.3970 (2)	0.1813 (4)	0.0398 (10)
H12B	−0.4429	0.3694	0.1379	0.048*
H12A	−0.4150	0.4218	0.2262	0.048*
C13	−0.1090 (6)	0.40176 (17)	0.0469 (3)	0.0317 (8)
H13A	−0.0405	0.4295	0.0018	0.038*
H13B	−0.2057	0.3734	−0.0006	0.038*
C14	0.0708 (7)	0.36460 (18)	0.1185 (4)	0.0369 (9)
H14B	0.1500	0.3397	0.0737	0.044*
H14A	0.1768	0.3929	0.1610	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1W	0.209 (18)	0.28 (2)	0.094 (9)	−0.004 (16)	0.091 (11)	0.013 (12)
O2W	0.47 (4)	0.202 (17)	0.077 (9)	0.11 (2)	0.049 (16)	−0.057 (12)
Zn1	0.0317 (4)	0.0194 (3)	0.0294 (3)	0.0006 (2)	0.0079 (2)	0.0028 (2)
O1	0.0276 (13)	0.0218 (12)	0.0333 (14)	0.0019 (9)	0.0089 (10)	0.0029 (10)
O2	0.073 (3)	0.062 (2)	0.060 (2)	0.040 (2)	0.0387 (19)	0.0275 (18)
O3	0.0378 (15)	0.0223 (12)	0.0368 (14)	0.0092 (10)	0.0116 (11)	0.0121 (11)
N1	0.065 (3)	0.0398 (19)	0.046 (2)	0.0223 (18)	0.0265 (19)	0.0195 (17)
N2	0.051 (2)	0.0282 (16)	0.0400 (18)	0.0135 (15)	0.0160 (16)	0.0124 (14)
N3	0.044 (2)	0.0361 (18)	0.055 (2)	0.0166 (16)	0.0219 (17)	0.0231 (17)
N4	0.0390 (19)	0.0283 (16)	0.0415 (18)	0.0096 (14)	0.0177 (15)	0.0119 (14)
N5	0.0265 (16)	0.0219 (14)	0.0324 (15)	0.0064 (12)	0.0028 (12)	0.0034 (13)
C1	0.037 (2)	0.0274 (18)	0.0316 (18)	0.0046 (15)	0.0112 (16)	−0.0002 (16)
C2	0.038 (2)	0.0238 (17)	0.0354 (19)	0.0070 (15)	0.0110 (16)	0.0035 (15)
C3	0.0283 (18)	0.0219 (16)	0.0302 (17)	0.0007 (13)	0.0032 (14)	0.0013 (14)
C4	0.036 (2)	0.0242 (17)	0.0318 (18)	0.0021 (15)	0.0087 (15)	0.0055 (15)
C5	0.048 (3)	0.033 (2)	0.043 (2)	0.0088 (18)	0.0188 (19)	0.0174 (18)
C6	0.033 (2)	0.0273 (18)	0.0380 (19)	0.0046 (15)	0.0078 (16)	0.0077 (16)
C7	0.044 (2)	0.0323 (19)	0.0347 (19)	0.0092 (17)	0.0137 (17)	0.0067 (17)
C8	0.060 (3)	0.037 (2)	0.046 (2)	0.018 (2)	0.026 (2)	0.0107 (19)
C9	0.083 (4)	0.063 (3)	0.062 (3)	0.030 (3)	0.038 (3)	0.024 (3)
C10	0.117 (7)	0.144 (9)	0.090 (5)	0.031 (6)	0.028 (5)	0.024 (6)
C11	0.055 (3)	0.045 (2)	0.047 (2)	0.025 (2)	0.021 (2)	0.020 (2)
C12	0.040 (2)	0.036 (2)	0.047 (2)	0.0157 (17)	0.0179 (18)	0.0161 (19)
C13	0.035 (2)	0.0247 (17)	0.0366 (19)	0.0101 (15)	0.0094 (16)	0.0081 (15)
C14	0.033 (2)	0.0293 (18)	0.051 (2)	0.0043 (16)	0.0147 (17)	0.0119 (18)

Geometric parameters (Å, º) top

Zn1—O1	2.031 (3)	C2—C8	1.370 (6)
Zn1—O1ⁱ	2.031 (3)	C2—C3	1.446 (5)
Zn1—O3ⁱ	2.107 (2)	C3—C4	1.444 (5)
Zn1—O3	2.107 (2)	C4—C7	1.399 (5)
Zn1—N5ⁱⁱ	2.275 (3)	C4—C5	1.401 (6)
Zn1—N5ⁱⁱⁱ	2.275 (3)	C5—H5	0.9300
O1—C1	1.253 (5)	C8—H8	0.9300
O2—C1	1.247 (5)	C9—C10	1.415 (11)
O3—C3	1.256 (4)	C9—H9B	0.9700
N1—C8	1.351 (5)	C9—H9A	0.9700
N1—C7	1.381 (5)	C10—H10C	0.9600
N1—C9	1.500 (6)	C10—H10B	0.9600
N2—C7	1.334 (5)	C10—H10A	0.9600
N2—C6	1.343 (5)	C11—C12	1.534 (5)
N3—C5	1.319 (5)	C11—H11B	0.9700
N3—C6	1.373 (5)	C11—H11A	0.9700
N4—C6	1.345 (5)	C12—H12B	0.9700
N4—C14	1.454 (5)	C12—H12A	0.9700
N4—C11	1.466 (5)	C13—C14	1.508 (5)
N5—C12	1.468 (5)	C13—H13A	0.9700
N5—C13	1.475 (5)	C13—H13B	0.9700
N5—Zn1^iv	2.275 (3)	C14—H14B	0.9700
N5—H5N	0.900 (10)	C14—H14A	0.9700
C1—C2	1.501 (5)

O1—Zn1—O1ⁱ	180.0	N2—C6—N4	117.3 (3)
O1—Zn1—O3ⁱ	92.90 (10)	N2—C6—N3	125.3 (4)
O1ⁱ—Zn1—O3ⁱ	87.10 (10)	N4—C6—N3	117.3 (4)
O1—Zn1—O3	87.10 (10)	N2—C7—N1	117.6 (3)
O1ⁱ—Zn1—O3	92.90 (10)	N2—C7—C4	123.6 (4)
O3ⁱ—Zn1—O3	180.0	N1—C7—C4	118.7 (3)
O1—Zn1—N5ⁱⁱ	89.74 (11)	N1—C8—C2	125.6 (4)
O1ⁱ—Zn1—N5ⁱⁱ	90.26 (11)	N1—C8—H8	117.2
O3ⁱ—Zn1—N5ⁱⁱ	90.86 (11)	C2—C8—H8	117.2
O3—Zn1—N5ⁱⁱ	89.14 (11)	C10—C9—N1	110.8 (7)
O1—Zn1—N5ⁱⁱⁱ	90.26 (11)	C10—C9—H9B	109.5
O1ⁱ—Zn1—N5ⁱⁱⁱ	89.74 (11)	N1—C9—H9B	109.5
O3ⁱ—Zn1—N5ⁱⁱⁱ	89.14 (11)	C10—C9—H9A	109.5
O3—Zn1—N5ⁱⁱⁱ	90.86 (11)	N1—C9—H9A	109.5
N5ⁱⁱ—Zn1—N5ⁱⁱⁱ	180.0	H9B—C9—H9A	108.1
C1—O1—Zn1	134.5 (2)	C9—C10—H10C	109.5
C3—O3—Zn1	127.6 (2)	C9—C10—H10B	109.5
C8—N1—C7	119.0 (3)	H10C—C10—H10B	109.5
C8—N1—C9	119.2 (4)	C9—C10—H10A	109.5
C7—N1—C9	121.8 (4)	H10C—C10—H10A	109.5
C7—N2—C6	116.3 (3)	H10B—C10—H10A	109.5
C5—N3—C6	115.3 (4)	N4—C11—C12	110.0 (3)
C6—N4—C14	121.2 (3)	N4—C11—H11B	109.7
C6—N4—C11	122.4 (3)	C12—C11—H11B	109.7
C14—N4—C11	113.0 (3)	N4—C11—H11A	109.7
C12—N5—C13	108.3 (3)	C12—C11—H11A	109.7
C12—N5—Zn1^iv	115.4 (2)	H11B—C11—H11A	108.2
C13—N5—Zn1^iv	112.8 (2)	N5—C12—C11	114.7 (3)
C12—N5—H5N	106 (4)	N5—C12—H12B	108.6
C13—N5—H5N	108 (4)	C11—C12—H12B	108.6
Zn1^iv—N5—H5N	106 (4)	N5—C12—H12A	108.6
O2—C1—O1	122.6 (4)	C11—C12—H12A	108.6
O2—C1—C2	117.7 (3)	H12B—C12—H12A	107.6
O1—C1—C2	119.7 (3)	N5—C13—C14	113.1 (3)
C8—C2—C3	118.6 (3)	N5—C13—H13A	109.0
C8—C2—C1	116.2 (3)	C14—C13—H13A	109.0
C3—C2—C1	125.2 (3)	N5—C13—H13B	109.0
O3—C3—C4	119.4 (3)	C14—C13—H13B	109.0
O3—C3—C2	125.8 (3)	H13A—C13—H13B	107.8
C4—C3—C2	114.7 (3)	N4—C14—C13	111.2 (3)
C7—C4—C5	114.1 (3)	N4—C14—H14B	109.4
C7—C4—C3	123.2 (4)	C13—C14—H14B	109.4
C5—C4—C3	122.6 (3)	N4—C14—H14A	109.4
N3—C5—C4	124.7 (4)	C13—C14—H14A	109.4
N3—C5—H5	117.6	H14B—C14—H14A	108.0
C4—C5—H5	117.6

O1ⁱ—Zn1—O1—C1	−50 (2)	C11—N4—C6—N2	−167.0 (4)
O3ⁱ—Zn1—O1—C1	179.5 (4)	C14—N4—C6—N3	171.7 (4)
O3—Zn1—O1—C1	−0.5 (4)	C11—N4—C6—N3	14.0 (6)
N5ⁱⁱ—Zn1—O1—C1	88.7 (4)	C5—N3—C6—N2	7.0 (7)
N5ⁱⁱⁱ—Zn1—O1—C1	−91.3 (4)	C5—N3—C6—N4	−174.0 (4)
O1—Zn1—O3—C3	0.4 (3)	C6—N2—C7—N1	−178.5 (4)
O1ⁱ—Zn1—O3—C3	−179.6 (3)	C6—N2—C7—C4	−1.0 (6)
O3ⁱ—Zn1—O3—C3	65 (100)	C8—N1—C7—N2	177.5 (4)
N5ⁱⁱ—Zn1—O3—C3	−89.4 (3)	C9—N1—C7—N2	−2.7 (7)
N5ⁱⁱⁱ—Zn1—O3—C3	90.6 (3)	C8—N1—C7—C4	−0.1 (7)
Zn1—O1—C1—O2	178.2 (3)	C9—N1—C7—C4	179.7 (5)
Zn1—O1—C1—C2	1.0 (6)	C5—C4—C7—N2	6.2 (6)
O2—C1—C2—C8	−0.1 (6)	C3—C4—C7—N2	−174.9 (4)
O1—C1—C2—C8	177.1 (4)	C5—C4—C7—N1	−176.3 (4)
O2—C1—C2—C3	−178.8 (4)	C3—C4—C7—N1	2.5 (6)
O1—C1—C2—C3	−1.6 (6)	C7—N1—C8—C2	−1.9 (8)
Zn1—O3—C3—C4	−179.0 (2)	C9—N1—C8—C2	178.3 (5)
Zn1—O3—C3—C2	−1.1 (5)	C3—C2—C8—N1	1.4 (7)
C8—C2—C3—O3	−177.0 (4)	C1—C2—C8—N1	−177.4 (4)
C1—C2—C3—O3	1.7 (6)	C8—N1—C9—C10	90.7 (7)
C8—C2—C3—C4	1.0 (6)	C7—N1—C9—C10	−89.1 (7)
C1—C2—C3—C4	179.7 (4)	C6—N4—C11—C12	−148.9 (4)
O3—C3—C4—C7	175.2 (4)	C14—N4—C11—C12	51.8 (5)
C2—C3—C4—C7	−2.9 (6)	C13—N5—C12—C11	53.7 (5)
O3—C3—C4—C5	−6.0 (6)	Zn1^iv—N5—C12—C11	−178.8 (3)
C2—C3—C4—C5	175.9 (4)	N4—C11—C12—N5	−52.7 (5)
C6—N3—C5—C4	−0.8 (7)	C12—N5—C13—C14	−55.0 (4)
C7—C4—C5—N3	−5.2 (7)	Zn1^iv—N5—C13—C14	176.0 (2)
C3—C4—C5—N3	175.9 (4)	C6—N4—C14—C13	145.9 (4)
C7—N2—C6—N4	174.8 (4)	C11—N4—C14—C13	−54.5 (5)
C7—N2—C6—N3	−6.2 (7)	N5—C13—C14—N4	56.5 (5)
C14—N4—C6—N2	−9.3 (6)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, y−1/2, −z+1/2; (iii) x+1, −y+1/2, z+1/2; (iv) −x, 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	0.91 (5)	2.28 (5)	3.168 (5)	166 (4)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₁₄H₁₆N₅O₃)₂]·2H₂O
M_r	704.05
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	6.1146 (12), 21.424 (4), 12.577 (3)
β (°)	101.10 (3)
V (Å³)	1616.9 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.82
Crystal size (mm)	0.36 × 0.28 × 0.18

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (CrystalStructure; Rigaku/MSC, 2002)
T_min, T_max	0.756, 0.866
No. of measured, independent and observed [I > 2σ(I)] reflections	15697, 3684, 2570
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.210, 1.06
No. of reflections	3684
No. of parameters	228
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)	0.83, −0.83

Computer programs: RAPID-AUTO (Rigaku, 1998), RAPID-AUTO (Rigaku , 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976).

Selected bond lengths (Å) top

Zn1—O1	2.031 (3)	Zn1—N5ⁱ	2.275 (3)
Zn1—O3	2.107 (2)

Symmetry code: (i) x+1, −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	0.91 (5)	2.28 (5)	3.168 (5)	166 (4)

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

Acknowledgements

The authors thank the Innovation Science Foundation of Harbin Medical University for financial support (grant No. 060041).

References

Huang, J., Hu, W.-P. & An, Z. (2008). Acta Cryst. E64, m547. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Mizuki, Y., Fujiwara, I. & Yamaguchi, T. (1996). J. Antimicrob. Chemother. 37 Suppl. A, 41–45. CrossRef Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. 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

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