Aqua­(di-2-pyridyl­amine-κ2N2,N2′)(pyridine-2,6-dicarboxyl­ato-κ3O2,N,O6)zinc monohydrate

Durkaya, F.; Dege, N.; Demirtaş, G.; Uçar, I.

doi:10.1107/S1600536811015571

metal-organic compounds

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Volume 67| Part 6| June 2011| Page m687

doi:10.1107/S1600536811015571

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Aqua(di-2-pyridylamine-κ²N²,N^2′)(pyridine-2,6-dicarboxylato-κ³O²,N,O⁶)zinc monohydrate

Figen Durkaya,^a ^* Necmi Dege,^b Güneş Demirtaş ^b and Ibrahim Uçar ^b

^aDepartment of Elementary Education, Elementary Science Education, Faculty of Education, Kırıkkale University, 71450 Yahşihan/Kırıkkale, Turkey, and ^bDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: durankayafigen@gmail.com

(Received 8 April 2011; accepted 25 April 2011; online 7 May 2011)

In the title compound, [Zn(C₇H₃NO₄)(C₁₀H₉N₃)(H₂O)]·H₂O, the Zn^II atom has a distorted octahedral coordination geometry. One of the water molecules is coordinated with the Zn^II ion and this molecule forms an O—H⋯O interaction with the lattice water molecule. The pyridine-2,6-dicarboxylate ligand is almost planar (r.m.s. deviation = 0.0242 Å). In the crystal, C—H⋯O, C—H⋯N, O—H⋯O and N—H⋯O hydrogen bonds are present.

Related literature

For the biological activity of 2,6-pyridinedicarboxylic acid, see: Chung et al. (1971 ); Tang et al. (1968 ). For the crystal structures of pyridine-2,6-dicarboxylate derivatives, see: Uçar et al. (2007a ,b ); Uçar et al. (2009 ); Cui et al. (2011 ). For C—H⋯O interactions, see: Desiraju & Steiner (1999 ).

Experimental

Crystal data

[Zn(C₇H₃NO₄)(C₁₀H₉N₃)(H₂O)]·H₂O
M_r = 437.71
Triclinic, $[P \overline 1]$
a = 6.8349 (5) Å
b = 11.1246 (8) Å
c = 12.1910 (9) Å
α = 96.109 (6)°
β = 96.404 (6)°
γ = 107.381 (6)°
V = 869.51 (11) Å³
Z = 2
Mo Kα radiation
μ = 1.46 mm⁻¹
T = 296 K
0.44 × 0.27 × 0.13 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.598, T_max = 0.833
7786 measured reflections
3398 independent reflections
3093 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.071
S = 1.05
3398 reflections
315 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯N4	0.93 (3)	2.59 (3)	3.189 (3)	123 (2)
O5—H5B⋯O6	0.82 (4)	1.95 (4)	2.750 (3)	166 (4)
N2—H5⋯O3ⁱ	0.75 (3)	2.08 (3)	2.823 (2)	172 (3)
O6—H6B⋯O1ⁱⁱ	0.86 (2)	2.05 (2)	2.832 (3)	151 (2)
O5—H5A⋯O2ⁱⁱⁱ	0.83 (4)	1.97 (4)	2.804 (3)	176 (3)
C2—H2⋯O2ⁱⁱ	0.94 (3)	2.56 (3)	3.432 (3)	155 (2)
C3—H3⋯O4^iv	0.86 (3)	2.41 (3)	3.117 (3)	140 (2)
C15—H15⋯O2^v	0.88 (3)	2.57 (3)	3.309 (3)	142 (2)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -z; (iii) x+1, y, z; (iv) x, y+1, z; (v) -x, -y, -z.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015571/zj2009sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015571/zj2009Isup2.hkl

checkCIF report

Comment top

The large amount of the 2,6-pyridinedicarboxylic acid (dipicolinic acid, DPA) is contain by bacterial spores and may be related to heat resistance of bacterial spores (Chung et al., 1971; Tang et al., 1968).

In the Figure 1 is shown that the pyridine-2,6-dicarboxylato ligand has connected to Zn^II ion through the carboxyl group and ring nitrogen. The metal atom has also connected to 2,2-dipyridylamine ligand thought two ring nitrogens. Thus, the Zn(II) atom has a distorted octahedral coordination geometry by two N atoms from the dipyridylamine ligand, one N atom and two O atoms from the pyridine-2,6-dicarboxylato ligand and one O atom from aqua ligand.

The a lot of crystal structures with pyridine-2,6-dicarboxylato ligand were reported in literature ( Uçar et al., 2007a; Uçar et al., 2007b; Uçar et al., 2009; Cui et al., 2011) and our crystal structre is very similar with the crystal structure reported by Uçar et al., (2007a). The Zn1—N1, Zn1—N3 and Zn1—N4 bond distances are 2.1318 (18) Å, 2.0327 (17) Å and 2.0269 (16) Å, respectively, while the Zn1—O1, Zn1—O3 and Zn1—O5 bond distances are 2.1947 (15) Å, 2.1755 (14) Å and 2.3148 (19) Å, respectively. In the crystal structure, the O3—C11—O4 and O1—C17—O2 bond angle for carboxylate groups are 126.5 (2)° and 126.4 (2)°, respectively. The some geometrical parameter were found as N1—Zn1—N3=89.01 (7)°, O3—Zn1—O1=152.19 (6)°, O1—Zn1—N4=75.75 (6)° and O3—Zn1—N4=76.80 (6)°.

The crystal structure contains intra and inter hydrogen bonds. The d parameter for C—H···O hydrogen bonds had separated a wide range and had different shapes for different donor atoms (Desiraju & Steiner, 1999). The d parameters of our crystal structure for H2···O2, H3···O4 and H15···O2 are 2.56 (3) Å, 2.41 (3) Å and 2.57 (3) Å, respectively. The D parameters for C—H···N interactions had given somewhat longer than C—H···O interactions (Desiraju & Steiner, 1999). The geometric parameters for C10—H10···N4 and C15—H15···O2 interactions are 0.93 (3) Å, 2.59 (3) Å, 3.189 (3) Å, 123 (2)° and 0.88 (3) Å, 2.57 (3) Å, 3.309 (3) Å, 142 (2)°, respectively. The d parameters for these interactions are 2.59 (3) Å and 2.57 (3) Å as well as d value for C10—H10···N4 is longer than d value for C15—H15···O2, but the D value is bigger for this interaction, due to the angle belong to C15—H15···O2 interaction is bigger than other interaction. The O5—H5B···O6 hydrogen bond is between the water molecules and the geometric parameters belong to this hydrogen bond are 0.82 (4) Å, 1.95 (4) Å, 2.750 (3) Å and 166 (4)°, respectively. The other hydrogen bonds have been given in Table 1.

Related literature top

For the biological activity of 2,6-pyridinedicarboxylic acid, see: Chung et al. (1971); Tang et al. (1968). For the crystal structures of pyridine-2,6-dicarboxylate derivatives, see: Uçar et al. (2007a,b); Uçar et al. (2009); Cui et al. (2011). For C—H···O interactions, see: Desiraju & Steiner (1999).

Experimental top

To ethanol/water (30ml, ca. 1:1, v/v) containing ZnCl₂.4H₂O (1mmol) and disodium dipicolinate (1mmol), 2,2-dipyridylamine (1mmol) was added slowly with continuous stirring. The resulting solutions were refluxed for 1h and then filtered. The blue filtrates were allowed about 2 weeks at room temperature, and then the colorless crystals of title complex suitable for X-ray diffraction analyses were collected.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing the atomic numbering scheme. Displacement ellipsoid are drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title compound in the unit cell. The hydrogen bonds were shown dashed lines.

Aqua(di-2-pyridylamine-κ²N²,N^2')(pyridine-2,6- dicarboxylato-κ³O²,N,O⁶)zinc monohydrate top

Crystal data top

[Zn(C₇H₃NO₄)(C₁₀H₉N₃)(H₂O)]·H₂O	Z = 2
M_r = 437.71	F(000) = 448
Triclinic, P1	D_x = 1.672 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8349 (5) Å	Cell parameters from 18443 reflections
b = 11.1246 (8) Å	θ = 2.4–27.4°
c = 12.1910 (9) Å	µ = 1.46 mm⁻¹
α = 96.109 (6)°	T = 296 K
β = 96.404 (6)°	Prism, colorless
γ = 107.381 (6)°	0.44 × 0.27 × 0.13 mm
V = 869.51 (11) Å³

Data collection top

Stoe IPDS 2 diffractometer	3398 independent reflections
Radiation source: fine-focus sealed tube	3093 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
w–scan rotation	θ_max = 26.0°, θ_min = 2.4°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −8→8
T_min = 0.598, T_max = 0.833	k = −13→13
7786 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.071	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0354P)² + 0.4854P] where P = (F_o² + 2F_c²)/3
3398 reflections	(Δ/σ)_max = 0.001
315 parameters	Δρ_max = 0.36 e Å⁻³
3 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

[Zn(C₇H₃NO₄)(C₁₀H₉N₃)(H₂O)]·H₂O	γ = 107.381 (6)°
M_r = 437.71	V = 869.51 (11) Å³
Triclinic, P1	Z = 2
a = 6.8349 (5) Å	Mo Kα radiation
b = 11.1246 (8) Å	µ = 1.46 mm⁻¹
c = 12.1910 (9) Å	T = 296 K
α = 96.109 (6)°	0.44 × 0.27 × 0.13 mm
β = 96.404 (6)°

Data collection top

Stoe IPDS 2 diffractometer	3398 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	3093 reflections with I > 2σ(I)
T_min = 0.598, T_max = 0.833	R_int = 0.019
7786 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	3 restraints
wR(F²) = 0.071	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.36 e Å⁻³
3398 reflections	Δρ_min = −0.51 e Å⁻³
315 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.8321 (4)	0.6257 (2)	0.2034 (2)	0.0405 (5)
C2	0.9281 (4)	0.7536 (2)	0.2147 (2)	0.0457 (5)
C3	1.0007 (4)	0.8203 (2)	0.3211 (2)	0.0448 (5)
C4	0.9665 (3)	0.7576 (2)	0.4108 (2)	0.0384 (5)
C5	0.8625 (3)	0.62585 (18)	0.39379 (17)	0.0305 (4)
C6	0.7053 (3)	0.45086 (19)	0.50443 (17)	0.0301 (4)
C7	0.6890 (3)	0.4313 (2)	0.61532 (19)	0.0371 (5)
C8	0.5781 (4)	0.3143 (2)	0.6365 (2)	0.0428 (5)
C9	0.4779 (4)	0.2187 (2)	0.5475 (2)	0.0457 (5)
C10	0.4947 (4)	0.2455 (2)	0.4423 (2)	0.0421 (5)
C11	0.8865 (3)	0.1646 (2)	0.28574 (18)	0.0373 (5)
C12	0.6742 (3)	0.10009 (19)	0.21539 (17)	0.0318 (4)
C13	0.5899 (4)	−0.0290 (2)	0.1784 (2)	0.0404 (5)
C14	0.3928 (4)	−0.0736 (2)	0.1172 (2)	0.0451 (6)
C15	0.2853 (3)	0.0102 (2)	0.0934 (2)	0.0400 (5)
C16	0.3784 (3)	0.13814 (19)	0.13253 (16)	0.0315 (4)
C17	0.2853 (3)	0.2443 (2)	0.11450 (17)	0.0353 (4)
N1	0.6108 (3)	0.35941 (16)	0.41824 (15)	0.0340 (4)
N2	0.8254 (3)	0.56958 (17)	0.48748 (16)	0.0328 (4)
N3	0.8026 (3)	0.55946 (16)	0.29092 (14)	0.0319 (4)
N4	0.5679 (3)	0.17928 (15)	0.19219 (14)	0.0301 (3)
O1	0.4027 (2)	0.35555 (15)	0.15426 (14)	0.0452 (4)
O2	0.1071 (2)	0.21538 (16)	0.06327 (14)	0.0456 (4)
O3	0.9333 (2)	0.28411 (14)	0.31253 (12)	0.0360 (3)
O4	0.9925 (3)	0.09778 (17)	0.31240 (19)	0.0629 (6)
O5	0.8755 (3)	0.38070 (19)	0.10477 (16)	0.0480 (4)
O6	0.7196 (4)	0.4353 (2)	−0.0951 (2)	0.0736 (6)
Zn1	0.69556 (4)	0.36631 (2)	0.25541 (2)	0.03462 (9)
H6A	0.598 (3)	0.411 (2)	−0.062 (2)	0.052*
H6B	0.727 (4)	0.5068 (19)	−0.118 (2)	0.052*
H1	0.788 (4)	0.577 (3)	0.131 (2)	0.046 (7)*
H2	0.937 (4)	0.790 (3)	0.149 (2)	0.054 (8)*
H3	1.064 (4)	0.901 (3)	0.331 (2)	0.051 (8)*
H4	1.005 (4)	0.797 (2)	0.483 (2)	0.039 (6)*
H5	0.881 (4)	0.612 (2)	0.540 (2)	0.032 (6)*
H5A	0.941 (5)	0.329 (3)	0.094 (3)	0.060 (9)*
H5B	0.818 (6)	0.384 (3)	0.043 (3)	0.077 (11)*
H7	0.754 (4)	0.499 (3)	0.672 (2)	0.045 (7)*
H8	0.567 (4)	0.299 (3)	0.709 (2)	0.046 (7)*
H9	0.391 (5)	0.139 (3)	0.558 (2)	0.059 (8)*
H10	0.427 (4)	0.185 (3)	0.380 (2)	0.047 (7)*
H13	0.661 (4)	−0.083 (3)	0.195 (2)	0.052 (8)*
H14	0.336 (4)	−0.159 (3)	0.092 (2)	0.053 (8)*
H15	0.160 (5)	−0.016 (3)	0.055 (2)	0.058 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0449 (12)	0.0410 (12)	0.0389 (12)	0.0179 (10)	0.0067 (9)	0.0071 (10)
C2	0.0487 (13)	0.0418 (13)	0.0538 (14)	0.0191 (11)	0.0142 (11)	0.0175 (11)
C3	0.0397 (12)	0.0277 (11)	0.0670 (16)	0.0088 (9)	0.0094 (11)	0.0105 (11)
C4	0.0347 (11)	0.0291 (10)	0.0480 (13)	0.0097 (8)	−0.0003 (9)	−0.0016 (9)
C5	0.0232 (9)	0.0277 (10)	0.0405 (11)	0.0108 (7)	−0.0005 (8)	0.0015 (8)
C6	0.0235 (9)	0.0304 (10)	0.0367 (10)	0.0116 (8)	−0.0002 (8)	0.0020 (8)
C7	0.0329 (10)	0.0413 (12)	0.0373 (11)	0.0142 (9)	0.0016 (9)	0.0032 (9)
C8	0.0398 (12)	0.0497 (14)	0.0442 (13)	0.0184 (10)	0.0102 (10)	0.0136 (11)
C9	0.0403 (12)	0.0372 (12)	0.0614 (15)	0.0101 (10)	0.0162 (11)	0.0119 (11)
C10	0.0381 (12)	0.0329 (11)	0.0493 (13)	0.0046 (9)	0.0074 (10)	−0.0011 (10)
C11	0.0351 (11)	0.0342 (11)	0.0404 (11)	0.0128 (9)	−0.0054 (9)	0.0014 (9)
C12	0.0320 (10)	0.0295 (10)	0.0327 (10)	0.0106 (8)	0.0003 (8)	0.0011 (8)
C13	0.0405 (12)	0.0298 (11)	0.0490 (13)	0.0121 (9)	0.0000 (10)	0.0024 (9)
C14	0.0428 (12)	0.0269 (11)	0.0560 (14)	0.0028 (9)	0.0006 (11)	−0.0049 (10)
C15	0.0304 (11)	0.0361 (11)	0.0440 (12)	0.0029 (9)	−0.0040 (9)	−0.0027 (9)
C16	0.0277 (9)	0.0326 (10)	0.0299 (10)	0.0064 (8)	−0.0008 (8)	0.0002 (8)
C17	0.0310 (10)	0.0376 (11)	0.0344 (10)	0.0106 (9)	−0.0033 (8)	0.0009 (9)
N1	0.0306 (8)	0.0285 (8)	0.0397 (9)	0.0070 (7)	0.0025 (7)	0.0006 (7)
N2	0.0327 (9)	0.0276 (9)	0.0322 (9)	0.0067 (7)	−0.0051 (7)	−0.0022 (7)
N3	0.0318 (8)	0.0286 (8)	0.0350 (9)	0.0106 (7)	0.0016 (7)	0.0031 (7)
N4	0.0294 (8)	0.0277 (8)	0.0300 (8)	0.0078 (7)	−0.0021 (6)	−0.0001 (7)
O1	0.0388 (8)	0.0328 (8)	0.0579 (10)	0.0125 (7)	−0.0144 (7)	−0.0006 (7)
O2	0.0343 (8)	0.0477 (9)	0.0491 (9)	0.0145 (7)	−0.0125 (7)	−0.0026 (7)
O3	0.0324 (7)	0.0308 (7)	0.0396 (8)	0.0092 (6)	−0.0078 (6)	−0.0010 (6)
O4	0.0539 (11)	0.0424 (10)	0.0875 (14)	0.0246 (8)	−0.0250 (10)	−0.0019 (9)
O5	0.0541 (10)	0.0532 (11)	0.0450 (10)	0.0274 (9)	0.0081 (8)	0.0114 (8)
O6	0.0919 (17)	0.0610 (13)	0.0670 (14)	0.0290 (12)	−0.0116 (12)	0.0154 (11)
Zn1	0.03612 (14)	0.02497 (13)	0.03752 (15)	0.00839 (9)	−0.00719 (10)	−0.00130 (9)

Geometric parameters (Å, º) top

C1—N3	1.360 (3)	C11—C12	1.525 (3)
C1—C2	1.362 (3)	C12—N4	1.332 (3)
C1—H1	0.95 (3)	C12—C13	1.381 (3)
C2—C3	1.382 (4)	C13—C14	1.384 (3)
C2—H2	0.94 (3)	C13—H13	0.90 (3)
C3—C4	1.363 (4)	C14—C15	1.383 (3)
C3—H3	0.86 (3)	C14—H14	0.91 (3)
C4—C5	1.406 (3)	C15—C16	1.380 (3)
C4—H4	0.92 (3)	C15—H15	0.88 (3)
C5—N3	1.339 (3)	C16—N4	1.334 (2)
C5—N2	1.372 (3)	C16—C17	1.523 (3)
C6—N1	1.336 (3)	C17—O2	1.237 (2)
C6—N2	1.382 (3)	C17—O1	1.266 (3)
C6—C7	1.403 (3)	N1—Zn1	2.1318 (18)
C7—C8	1.364 (3)	N2—H5	0.75 (3)
C7—H7	0.93 (3)	N3—Zn1	2.0327 (17)
C8—C9	1.389 (4)	N4—Zn1	2.0269 (16)
C8—H8	0.93 (3)	O1—Zn1	2.1947 (15)
C9—C10	1.357 (4)	O3—Zn1	2.1755 (14)
C9—H9	0.94 (3)	O5—Zn1	2.3148 (19)
C10—N1	1.361 (3)	O5—H5A	0.83 (4)
C10—H10	0.93 (3)	O5—H5B	0.82 (4)
C11—O4	1.226 (3)	O6—H6A	0.944 (16)
C11—O3	1.268 (3)	O6—H6B	0.860 (17)

N3—C1—C2	123.8 (2)	C16—C15—C14	118.5 (2)
N3—C1—H1	116.2 (16)	C16—C15—H15	120 (2)
C2—C1—H1	119.9 (16)	C14—C15—H15	121.7 (19)
C1—C2—C3	118.3 (2)	N4—C16—C15	120.37 (19)
C1—C2—H2	116.5 (18)	N4—C16—C17	113.52 (17)
C3—C2—H2	125.2 (18)	C15—C16—C17	126.11 (18)
C4—C3—C2	119.4 (2)	O2—C17—O1	126.4 (2)
C4—C3—H3	120.3 (19)	O2—C17—C16	118.48 (19)
C2—C3—H3	120.4 (19)	O1—C17—C16	115.11 (17)
C3—C4—C5	119.7 (2)	C6—N1—C10	117.04 (19)
C3—C4—H4	123.9 (16)	C6—N1—Zn1	122.80 (14)
C5—C4—H4	116.5 (16)	C10—N1—Zn1	118.08 (15)
N3—C5—N2	122.07 (18)	C5—N2—C6	133.38 (18)
N3—C5—C4	121.2 (2)	C5—N2—H5	113.4 (19)
N2—C5—C4	116.70 (19)	C6—N2—H5	113.2 (19)
N1—C6—N2	120.82 (19)	C5—N3—C1	117.46 (18)
N1—C6—C7	122.11 (19)	C5—N3—Zn1	125.03 (14)
N2—C6—C7	117.06 (18)	C1—N3—Zn1	117.26 (15)
C8—C7—C6	119.2 (2)	C12—N4—C16	121.92 (17)
C8—C7—H7	122.3 (16)	C12—N4—Zn1	118.39 (13)
C6—C7—H7	118.4 (16)	C16—N4—Zn1	119.64 (14)
C7—C8—C9	119.1 (2)	C17—O1—Zn1	115.49 (13)
C7—C8—H8	120.6 (17)	C11—O3—Zn1	115.28 (12)
C9—C8—H8	120.2 (17)	Zn1—O5—H5A	117 (2)
C10—C9—C8	118.5 (2)	Zn1—O5—H5B	120 (3)
C10—C9—H9	119.6 (18)	H5A—O5—H5B	106 (3)
C8—C9—H9	121.8 (18)	H6A—O6—H6B	107 (2)
C9—C10—N1	123.9 (2)	N4—Zn1—N3	169.48 (7)
C9—C10—H10	121.3 (17)	N4—Zn1—N1	98.90 (7)
N1—C10—H10	114.8 (17)	N3—Zn1—N1	89.01 (7)
O4—C11—O3	126.5 (2)	N4—Zn1—O3	76.80 (6)
O4—C11—C12	118.25 (19)	N3—Zn1—O3	110.79 (6)
O3—C11—C12	115.21 (18)	N1—Zn1—O3	86.62 (6)
N4—C12—C13	120.53 (18)	N4—Zn1—O1	75.75 (6)
N4—C12—C11	114.27 (17)	N3—Zn1—O1	95.92 (6)
C13—C12—C11	125.19 (19)	N1—Zn1—O1	101.92 (7)
C12—C13—C14	118.4 (2)	O3—Zn1—O1	152.19 (6)
C12—C13—H13	120.5 (18)	N4—Zn1—O5	85.73 (7)
C14—C13—H13	121.1 (18)	N3—Zn1—O5	88.44 (7)
C15—C14—C13	120.2 (2)	N1—Zn1—O5	164.45 (7)
C15—C14—H14	120.7 (18)	O3—Zn1—O5	79.96 (7)
C13—C14—H14	119.1 (18)	O1—Zn1—O5	93.61 (7)

N3—C1—C2—C3	0.3 (4)	C15—C16—N4—Zn1	−176.87 (16)
C1—C2—C3—C4	−2.7 (4)	C17—C16—N4—Zn1	3.2 (2)
C2—C3—C4—C5	1.4 (3)	O2—C17—O1—Zn1	173.65 (19)
C3—C4—C5—N3	2.5 (3)	C16—C17—O1—Zn1	−6.8 (2)
C3—C4—C5—N2	−177.3 (2)	O4—C11—O3—Zn1	−176.9 (2)
N1—C6—C7—C8	1.9 (3)	C12—C11—O3—Zn1	1.7 (2)
N2—C6—C7—C8	−177.71 (19)	C12—N4—Zn1—N3	139.2 (3)
C6—C7—C8—C9	−2.3 (3)	C16—N4—Zn1—N3	−43.2 (4)
C7—C8—C9—C10	0.2 (4)	C12—N4—Zn1—N1	−82.39 (16)
C8—C9—C10—N1	2.5 (4)	C16—N4—Zn1—N1	95.14 (16)
O4—C11—C12—N4	178.7 (2)	C12—N4—Zn1—O3	1.98 (15)
O3—C11—C12—N4	0.0 (3)	C16—N4—Zn1—O3	179.51 (16)
O4—C11—C12—C13	−0.1 (4)	C12—N4—Zn1—O1	177.47 (17)
O3—C11—C12—C13	−178.9 (2)	C16—N4—Zn1—O1	−4.99 (15)
N4—C12—C13—C14	−0.2 (3)	C12—N4—Zn1—O5	82.65 (16)
C11—C12—C13—C14	178.5 (2)	C16—N4—Zn1—O5	−99.81 (16)
C12—C13—C14—C15	0.5 (4)	C5—N3—Zn1—N4	162.2 (3)
C13—C14—C15—C16	−0.3 (4)	C1—N3—Zn1—N4	−23.7 (5)
C14—C15—C16—N4	−0.2 (3)	C5—N3—Zn1—N1	23.17 (16)
C14—C15—C16—C17	179.7 (2)	C1—N3—Zn1—N1	−162.73 (16)
N4—C16—C17—O2	−177.65 (19)	C5—N3—Zn1—O3	−62.84 (17)
C15—C16—C17—O2	2.4 (3)	C1—N3—Zn1—O3	111.27 (16)
N4—C16—C17—O1	2.7 (3)	C5—N3—Zn1—O1	125.05 (16)
C15—C16—C17—O1	−177.2 (2)	C1—N3—Zn1—O1	−60.85 (16)
N2—C6—N1—C10	−179.72 (19)	C5—N3—Zn1—O5	−141.49 (16)
C7—C6—N1—C10	0.7 (3)	C1—N3—Zn1—O5	32.62 (16)
N2—C6—N1—Zn1	17.0 (3)	C6—N1—Zn1—N4	160.71 (15)
C7—C6—N1—Zn1	−162.58 (15)	C10—N1—Zn1—N4	−2.40 (17)
C9—C10—N1—C6	−3.0 (3)	C6—N1—Zn1—N3	−26.25 (16)
C9—C10—N1—Zn1	161.11 (19)	C10—N1—Zn1—N3	170.64 (17)
N3—C5—N2—C6	−10.9 (3)	C6—N1—Zn1—O3	84.64 (16)
C4—C5—N2—C6	168.9 (2)	C10—N1—Zn1—O3	−78.47 (16)
N1—C6—N2—C5	6.7 (3)	C6—N1—Zn1—O1	−122.10 (16)
C7—C6—N2—C5	−173.7 (2)	C10—N1—Zn1—O1	74.79 (17)
N2—C5—N3—C1	174.93 (19)	C6—N1—Zn1—O5	54.4 (3)
C4—C5—N3—C1	−4.8 (3)	C10—N1—Zn1—O5	−108.8 (3)
N2—C5—N3—Zn1	−11.0 (3)	C11—O3—Zn1—N4	−1.98 (15)
C4—C5—N3—Zn1	169.25 (15)	C11—O3—Zn1—N3	−174.37 (15)
C2—C1—N3—C5	3.6 (3)	C11—O3—Zn1—N1	97.98 (16)
C2—C1—N3—Zn1	−171.01 (19)	C11—O3—Zn1—O1	−11.4 (2)
C13—C12—N4—C16	−0.4 (3)	C11—O3—Zn1—O5	−89.92 (16)
C11—C12—N4—C16	−179.23 (18)	C17—O1—Zn1—N4	6.50 (16)
C13—C12—N4—Zn1	177.11 (17)	C17—O1—Zn1—N3	179.98 (17)
C11—C12—N4—Zn1	−1.8 (2)	C17—O1—Zn1—N1	−89.78 (17)
C15—C16—N4—C12	0.6 (3)	C17—O1—Zn1—O3	15.9 (3)
C17—C16—N4—C12	−179.36 (18)	C17—O1—Zn1—O5	91.17 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···N4	0.93 (3)	2.59 (3)	3.189 (3)	123 (2)
O5—H5B···O6	0.82 (4)	1.95 (4)	2.750 (3)	166 (4)
N2—H5···O3ⁱ	0.75 (3)	2.08 (3)	2.823 (2)	172 (3)
O6—H6B···O1ⁱⁱ	0.86 (2)	2.05 (2)	2.832 (3)	151 (2)
O5—H5A···O2ⁱⁱⁱ	0.83 (4)	1.97 (4)	2.804 (3)	176 (3)
C2—H2···O2ⁱⁱ	0.94 (3)	2.56 (3)	3.432 (3)	155 (2)
C3—H3···O4^iv	0.86 (3)	2.41 (3)	3.117 (3)	140 (2)
C15—H15···O2^v	0.88 (3)	2.57 (3)	3.309 (3)	142 (2)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₇H₃NO₄)(C₁₀H₉N₃)(H₂O)]·H₂O
M_r	437.71
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.8349 (5), 11.1246 (8), 12.1910 (9)
α, β, γ (°)	96.109 (6), 96.404 (6), 107.381 (6)
V (Å³)	869.51 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.46
Crystal size (mm)	0.44 × 0.27 × 0.13

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.598, 0.833
No. of measured, independent and observed [I > 2σ(I)] reflections	7786, 3398, 3093
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.071, 1.05
No. of reflections	3398
No. of parameters	315
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.51

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···N4	0.93 (3)	2.59 (3)	3.189 (3)	123 (2)
O5—H5B···O6	0.82 (4)	1.95 (4)	2.750 (3)	166 (4)
N2—H5···O3ⁱ	0.75 (3)	2.08 (3)	2.823 (2)	172 (3)
O6—H6B···O1ⁱⁱ	0.860 (17)	2.05 (2)	2.832 (3)	151 (2)
O5—H5A···O2ⁱⁱⁱ	0.83 (4)	1.97 (4)	2.804 (3)	176 (3)
C2—H2···O2ⁱⁱ	0.94 (3)	2.56 (3)	3.432 (3)	155 (2)
C3—H3···O4^iv	0.86 (3)	2.41 (3)	3.117 (3)	140 (2)
C15—H15···O2^v	0.88 (3)	2.57 (3)	3.309 (3)	142 (2)

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

Acknowledgements

The authors thank the Ondokuz Mayis University Research Fund for financial support.

References

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