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

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

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809036939/hb5062sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809036939/hb5062Isup2.hkl Contains datablock I

CCDC reference: 750555

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.006 Å
H-atom completeness 89%
Disorder in solvent or counterion
R factor = 0.057
wR factor = 0.210
Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.28 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.58 Ratio
PLAT430_ALERT_2_B Short Inter D...A Contact  O1W    ..  O2      ..       2.84 Ang.
PLAT731_ALERT_1_B Bond    Calc     0.91(5), Rep   0.900(10) ......       5.00 su-Ra
              N5   -H5N     1.555   1.555

Alert level C
CHEMW01_ALERT_1_C  The difference between the given and expected weight for
            compound is greater 1 mass unit. Check that all hydrogen
            atoms have been taken into account.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.31
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C9     -   C10    ...       1.41 Ang.
PLAT430_ALERT_2_C Short Inter D...A Contact  O2     ..  O2W     ..       2.85 Ang.
PLAT041_ALERT_1_C Calc. and Reported SumFormula    Strings  Differ          ?
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ          ?
PLAT194_ALERT_1_C Missing _cell_measurement_reflns_used datum ....          ?
PLAT195_ALERT_1_C Missing _cell_measurement_theta_max   datum ....          ?
PLAT196_ALERT_1_C Missing _cell_measurement_theta_min   datum ....          ?
PLAT234_ALERT_4_C Large Hirshfeld Difference C9     --  C10     ..       0.16 Ang.

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C28 H36 N10 O8 Zn1
            Atom count from the _atom_site data:  C28 H32 N10 O8 Zn1
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    2
           From the CIF: _chemical_formula_sum  C28 H36 N10 O8 Zn
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         56.00     56.00    0.00
           H         72.00     64.00    8.00
           N         20.00     20.00    0.00
           O         16.00     16.00    0.00
           Zn         2.00      2.00    0.00
PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large..       0.13
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1
PLAT302_ALERT_4_G Note: Anion/Solvent Disorder ...................      50.00 Perc.
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            O1  -ZN1 -O1  -C1    -50.00  2.00   3.656   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          8
            O3  -ZN1 -O3  -C3      7.00  0.00   3.656   1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   8 ALERT level G = General alerts; check

   9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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.