catena-Poly[[[aqua­(pyrazine-2-carboxamide-κ2N1,O)zinc]-μ-pyrazine-2-carboxamide-κ3N1,O:N4] dinitrate]

Shirvan, S.A.; Haydari Dezfuli, S.

doi:10.1107/S1600536812016017

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages m627-m628

doi:10.1107/S1600536812016017

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catena-Poly[[[aqua(pyrazine-2-carboxamide-κ²N¹,O)zinc]-μ-pyrazine-2-carboxamide-κ³N¹,O:N⁴] dinitrate]

Sadif A. Shirvan ^a ^* and Sara Haydari Dezfuli ^a

^aDepartment of Chemistry, Omidieh Branch, Islamic Azad University, Omidieh, Iran
^*Correspondence e-mail: sadif.shirvan1@gmail.com

(Received 31 March 2012; accepted 12 April 2012; online 18 April 2012)

In the crystal of the title compound, {[Zn(C₅H₅N₃O)₂(H₂O)](NO₃)₂}_n, the Zn^II cation is N,O-chelated by two pyrazine-2-carboxamide (PCA) ligands and is further coordinated by one water molecule and by one pyrazine-N atom from an adjacent PCA ligand in a distorted ZnN₃O₃ octahedral geometry. One of the two independent PCA ligands bridges two Zn^II cations, forming a zigzag polymeric chain running along the c axis. In the crystal, the NO₃⁻ anions link to the chain via O—H⋯O and N—H⋯O hydrogen bonding. Weak intermolecular C—H⋯O interactions also occur.

Related literature

For related structures, see: Shirvan & Haydari Dezfuli (2012 ); Abu-Youssef et al. (2006 ); Azhdari Tehrani et al. (2010 ); Goher & Mautner (2000 ); Kristiansson (2002 ); Mir Mohammad Sadegh et al. (2010 ); Munakata et al. (1997 ); Pacigova et al. (2008 ).

Experimental

Crystal data

[Zn(C₅H₅N₃O)₂(H₂O)](NO₃)₂
M_r = 453.67
Monoclinic, P 2₁ /c
a = 10.4889 (11) Å
b = 15.7477 (16) Å
c = 9.9332 (10) Å
β = 97.664 (8)°
V = 1626.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.58 mm⁻¹
T = 298 K
0.23 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.070, T_max = 0.240
9288 measured reflections
3192 independent reflections
2088 reflections with I > 2σ(I)
R_int = 0.123

Refinement

R[F² > 2σ(F²)] = 0.076
wR(F²) = 0.103
S = 1.06
3192 reflections
261 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O1	2.064 (3)
Zn1—O2	2.073 (3)
Zn1—O3	2.042 (6)
Zn1—N1	2.180 (5)
Zn1—N4	2.193 (5)
Zn1—N5ⁱ	2.179 (5)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3B⋯O8ⁱⁱ	0.76 (7)	2.05 (7)	2.810 (8)	177 (7)
O3—H3C⋯O4	0.75 (6)	2.06 (7)	2.781 (8)	162 (9)
N3—H3D⋯O3ⁱⁱ	0.86	2.50	3.193 (8)	138
N3—H3D⋯O5ⁱⁱ	0.86	2.42	3.163 (8)	144
N3—H3E⋯O7	0.86	2.08	2.937 (8)	172
N6—H6B⋯O4ⁱⁱⁱ	0.86	2.07	2.913 (7)	166
N6—H6C⋯O5^iv	0.86	2.41	3.231 (8)	161
C1—H1⋯O8^v	0.93	2.39	3.292 (8)	162
C3—H3⋯O7	0.93	2.31	3.227 (8)	169
C6—H6⋯O6^vi	0.93	2.60	3.295 (8)	132
C7—H7⋯O5^vi	0.93	2.49	3.362 (8)	156
C8—H8⋯O4ⁱⁱⁱ	0.93	2.39	3.298 (7)	167
Symmetry codes: (ii) -x+1, -y+1, -z+1; (iii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) -x+2, -y+1, -z+1; (v) x+1, y, z; (vi) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812016017/xu5508sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812016017/xu5508Isup2.hkl

checkCIF report

Comment top

In a recent paper, we reported the synthesis and crystal structure of [ZnBr₂(pzc)₂] (Shirvan & Haydari Dezfuli, 2012), where pzc is the pyrazine-2-carboxamide. Pyrazine-2-carboxamide is a good ligand, and a few complexes with pzc have been prepared, such as that of mercury (Azhdari Tehrani et al., 2010; Mir Mohammad Sadegh et al., 2010) and vanadium (Pacigova et al., 2008), manganese (Abu-Youssef et al., 2006) and copper (Kristiansson, 2002; Munakata et al., 1997; Goher & Mautner, 2000). Here, we report the synthesis and structure of the title compound.

The asymmetric unit of the title compound, (Fig. 1), contains one Zn^II cation, two pyrazine-2-carboxamide ligands, one water molecule and two NO₃^- counter-ions. The Zn^II atom is six-coordinated in a distorted octahedral configuration by two N and two O atoms from two pyrazine-2-carboxamide ligands and one O atom from one water molecule. The sixth coordination site is occupied by N atom from one bridging pyrazine-2-carboxamide ligand. The Zn—O and Zn—N bond lengths and angles are collected in Table 1.

In the crystal structure, intra and intermolecular O—H···O, N—H···O and C—H···O hydrogen bonds (Table 2, Fig. 2) may stabilize the structure.

Related literature top

For related structures, see: Shirvan & Haydari Dezfuli (2012); Abu-Youssef et al. (2006); Azhdari Tehrani et al. (2010); Goher & Mautner (2000); Kristiansson (2002); Mir Mohammad Sadegh et al. (2010); Munakata et al. (1997); Pacigova et al. (2008).

Experimental top

A solution of pyrazine-2-carboxamide (0.25 g, 2.0 mmol) in methanol (10 ml) was added to a solution of Zn(NO₃)₂.4H₂O (0.26 g, 1.0 mmol) in methanol (10 ml) and the resulting colorless solution was stirred for 15 min at room temperature. This solution was left to evaporate slowly at room temperature. After one week, colorless block crystals of the title compound were isolated (yield 0.36 g, 79.3%).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (b) x,3/2 - y,1/2 + z].
	Fig. 2. Unit-cell packing diagram for title molecule. Hydrogen bonds are shown as dashed lines.

catena-Poly[[[aqua(pyrazine-2-carboxamide- κ²N¹,O)zinc]-µ-pyrazine-2-carboxamide- κ³N¹,O:N⁴] dinitrate] top

Crystal data top

[Zn(C₅H₅N₃O)₂(H₂O)](NO₃)₂	F(000) = 920
M_r = 453.67	D_x = 1.853 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9288 reflections
a = 10.4889 (11) Å	θ = 2.4–26.0°
b = 15.7477 (16) Å	µ = 1.58 mm⁻¹
c = 9.9332 (10) Å	T = 298 K
β = 97.664 (8)°	Block, colorless
V = 1626.1 (3) Å³	0.23 × 0.12 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII CCD area detector diffractometer	3192 independent reflections
Radiation source: fine-focus sealed tube	2088 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.123
ω scans	θ_max = 26.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
T_min = 0.070, T_max = 0.240	k = −19→19
9288 measured reflections	l = −12→11

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0237P)²] where P = (F_o² + 2F_c²)/3
3192 reflections	(Δ/σ)_max = 0.006
261 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

[Zn(C₅H₅N₃O)₂(H₂O)](NO₃)₂	V = 1626.1 (3) Å³
M_r = 453.67	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.4889 (11) Å	µ = 1.58 mm⁻¹
b = 15.7477 (16) Å	T = 298 K
c = 9.9332 (10) Å	0.23 × 0.12 × 0.10 mm
β = 97.664 (8)°

Data collection top

Bruker APEXII CCD area detector diffractometer	3192 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2088 reflections with I > 2σ(I)
T_min = 0.070, T_max = 0.240	R_int = 0.123
9288 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.076	0 restraints
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.46 e Å⁻³
3192 reflections	Δρ_min = −0.52 e Å⁻³
261 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
C1	0.7871 (6)	0.4587 (4)	0.1320 (7)	0.0329 (15)
H1	0.8748	0.4701	0.1417	0.039*
C2	0.7334 (6)	0.4048 (5)	0.0291 (7)	0.0445 (17)
H2	0.7859	0.3819	−0.0300	0.053*
C3	0.5393 (6)	0.4184 (4)	0.1012 (7)	0.0387 (16)
H3	0.4526	0.4043	0.0946	0.046*
C4	0.5906 (5)	0.4738 (3)	0.2038 (6)	0.0210 (12)
C5	0.5169 (5)	0.5161 (3)	0.3017 (6)	0.0237 (13)
C6	0.6418 (5)	0.7234 (4)	0.1580 (7)	0.0248 (14)
H6	0.5624	0.7048	0.1782	0.030*
C7	0.6463 (5)	0.7868 (4)	0.0610 (7)	0.0292 (15)
H7	0.5699	0.8084	0.0154	0.035*
C8	0.8651 (5)	0.7831 (3)	0.0990 (6)	0.0240 (14)
H8	0.9445	0.8033	0.0814	0.029*
C9	0.8615 (5)	0.7189 (3)	0.1932 (6)	0.0189 (12)
C10	0.9758 (5)	0.6759 (3)	0.2712 (6)	0.0207 (13)
N1	0.7158 (4)	0.4940 (3)	0.2159 (5)	0.0246 (12)
N2	0.6089 (5)	0.3848 (4)	0.0128 (6)	0.0483 (16)
N3	0.3939 (5)	0.5002 (3)	0.3014 (6)	0.0366 (14)
H3D	0.3515	0.5264	0.3571	0.044*
H3E	0.3558	0.4637	0.2454	0.044*
N4	0.7479 (4)	0.6893 (3)	0.2219 (5)	0.0228 (12)
N5	0.7584 (4)	0.8170 (3)	0.0325 (5)	0.0225 (11)
N6	1.0915 (4)	0.7048 (3)	0.2613 (5)	0.0317 (13)
H6C	1.1576	0.6814	0.3071	0.038*
H6B	1.1012	0.7472	0.2090	0.038*
N7	0.7146 (5)	0.3192 (3)	0.4190 (7)	0.0350 (13)
N8	0.1273 (5)	0.4024 (4)	0.1241 (6)	0.0361 (13)
O1	0.5749 (3)	0.5684 (2)	0.3812 (4)	0.0300 (11)
O2	0.9561 (3)	0.6152 (2)	0.3448 (4)	0.0252 (9)
O3	0.8371 (5)	0.5012 (4)	0.5193 (6)	0.0397 (13)
H3C	0.850 (7)	0.456 (4)	0.503 (8)	0.04 (3)*
H3B	0.853 (6)	0.510 (4)	0.595 (7)	0.03 (2)*
O4	0.8335 (4)	0.3362 (3)	0.4190 (5)	0.0437 (12)
O5	0.6640 (5)	0.3426 (4)	0.5181 (7)	0.080 (2)
O6	0.6571 (5)	0.2815 (4)	0.3235 (6)	0.0633 (16)
O7	0.2393 (5)	0.3816 (3)	0.1188 (7)	0.0622 (15)
O8	0.1027 (5)	0.4586 (4)	0.2039 (6)	0.0669 (17)
O9	0.0400 (5)	0.3687 (4)	0.0522 (8)	0.098 (3)
Zn1	0.76855 (6)	0.58798 (4)	0.37477 (7)	0.02037 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.021 (3)	0.037 (3)	0.042 (4)	0.001 (3)	0.007 (3)	−0.005 (3)
C2	0.044 (4)	0.049 (4)	0.041 (4)	0.003 (4)	0.008 (3)	−0.020 (4)
C3	0.030 (3)	0.048 (4)	0.038 (4)	−0.012 (3)	0.004 (3)	−0.020 (4)
C4	0.020 (3)	0.028 (3)	0.015 (3)	−0.003 (2)	0.000 (2)	−0.001 (3)
C5	0.023 (3)	0.023 (3)	0.025 (4)	−0.003 (2)	−0.001 (3)	0.005 (3)
C6	0.018 (3)	0.025 (3)	0.033 (4)	−0.004 (2)	0.007 (3)	0.006 (3)
C7	0.013 (3)	0.035 (4)	0.039 (4)	0.001 (2)	0.001 (3)	0.003 (3)
C8	0.021 (3)	0.019 (3)	0.033 (4)	0.001 (2)	0.007 (3)	−0.001 (3)
C9	0.017 (3)	0.020 (3)	0.018 (3)	−0.002 (2)	0.001 (2)	−0.001 (2)
C10	0.022 (3)	0.021 (3)	0.020 (3)	0.003 (2)	0.004 (2)	−0.004 (3)
N1	0.021 (2)	0.030 (3)	0.023 (3)	−0.001 (2)	0.003 (2)	0.003 (2)
N2	0.038 (3)	0.060 (4)	0.046 (4)	−0.004 (3)	0.003 (3)	−0.021 (3)
N3	0.023 (3)	0.052 (3)	0.035 (4)	−0.004 (2)	0.009 (2)	−0.011 (3)
N4	0.020 (2)	0.020 (3)	0.029 (3)	0.000 (2)	0.006 (2)	0.003 (2)
N5	0.022 (2)	0.024 (2)	0.021 (3)	0.005 (2)	0.004 (2)	−0.002 (2)
N6	0.015 (2)	0.039 (3)	0.041 (4)	0.001 (2)	0.003 (2)	0.017 (3)
N7	0.027 (3)	0.025 (3)	0.053 (4)	0.002 (2)	0.004 (3)	−0.004 (3)
N8	0.030 (3)	0.035 (3)	0.042 (4)	0.003 (3)	0.002 (3)	0.001 (3)
O1	0.022 (2)	0.034 (3)	0.035 (3)	−0.0099 (18)	0.0051 (19)	−0.017 (2)
O2	0.020 (2)	0.025 (2)	0.031 (3)	0.0002 (16)	0.0029 (18)	0.0098 (18)
O3	0.053 (3)	0.034 (3)	0.030 (4)	0.009 (3)	0.000 (3)	0.005 (3)
O4	0.024 (2)	0.052 (3)	0.056 (4)	0.001 (2)	0.007 (2)	−0.017 (3)
O5	0.063 (4)	0.087 (4)	0.103 (5)	−0.015 (3)	0.057 (4)	−0.041 (4)
O6	0.045 (3)	0.077 (4)	0.063 (4)	−0.022 (3)	−0.009 (3)	−0.006 (3)
O7	0.028 (3)	0.065 (3)	0.094 (4)	−0.006 (3)	0.010 (3)	−0.022 (3)
O8	0.052 (3)	0.088 (4)	0.056 (4)	0.018 (3)	−0.009 (3)	−0.039 (3)
O9	0.026 (3)	0.135 (6)	0.127 (6)	0.003 (3)	−0.007 (3)	−0.092 (5)
Zn1	0.0182 (3)	0.0208 (3)	0.0216 (3)	−0.0026 (3)	0.0009 (2)	−0.0004 (4)

Geometric parameters (Å, º) top

Zn1—O1	2.064 (3)	N4—C9	1.345 (7)
Zn1—O2	2.073 (3)	N4—C6	1.320 (7)
Zn1—O3	2.042 (6)	N5—C8	1.333 (7)
Zn1—N1	2.180 (5)	N5—C7	1.333 (7)
Zn1—N4	2.193 (5)	N6—C10	1.312 (7)
Zn1—N5ⁱ	2.179 (5)	N3—H3E	0.8600
O1—C5	1.243 (6)	N3—H3D	0.8600
O2—C10	1.237 (6)	N6—H6B	0.8600
O3—H3B	0.76 (7)	N6—H6C	0.8600
O3—H3C	0.75 (6)	C1—C2	1.389 (10)
O4—N7	1.276 (7)	C3—C4	1.394 (9)
O5—N7	1.235 (9)	C4—C5	1.479 (8)
O6—N7	1.210 (9)	C6—C7	1.393 (9)
O7—N8	1.227 (8)	C8—C9	1.382 (7)
O8—N8	1.238 (9)	C9—C10	1.500 (8)
O9—N8	1.207 (9)	C1—H1	0.9300
N1—C4	1.341 (7)	C2—H2	0.9300
N1—C1	1.315 (8)	C3—H3	0.9300
N2—C2	1.332 (8)	C6—H6	0.9300
N2—C3	1.325 (9)	C7—H7	0.9300
N3—C5	1.314 (7)	C8—H8	0.9300

Zn1···H3Dⁱⁱ	3.5800	N4···C10	2.385 (7)
O1···O3	3.092 (6)	N4···N5ⁱ	3.074 (7)
O1···N1	2.627 (6)	N5···N4^viii	3.074 (7)
O1···N4	3.192 (6)	N5···O3^viii	2.987 (8)
O1···C4	2.330 (7)	N5···O1^viii	2.907 (6)
O1···O5ⁱⁱ	3.148 (7)	N5···N4	2.766 (7)
O1···N5ⁱ	2.907 (6)	N5···O2^viii	3.154 (6)
O1···C7ⁱ	2.932 (7)	N6···O6^ix	3.117 (7)
O2···C9	2.350 (6)	N6···O4^ix	2.913 (7)
O2···O3	2.892 (7)	N6···O4ⁱⁱⁱ	3.233 (7)
O2···N4	2.629 (6)	N6···O5ⁱⁱⁱ	3.231 (8)
O2···C8ⁱ	3.240 (7)	N7···C4	3.383 (8)
O2···O3ⁱⁱⁱ	3.018 (7)	N7···O3	3.243 (8)
O2···O4ⁱⁱⁱ	3.095 (6)	N8···C8^v	3.323 (8)
O2···N5ⁱ	3.154 (6)	N8···C9^v	3.406 (8)
O3···N1	3.113 (8)	N2···H6^vii	2.8100
O3···O5	3.087 (8)	N3···H3Bⁱⁱ	2.92 (6)
O3···N5ⁱ	2.987 (8)	N3···H3	2.6900
O3···O2ⁱⁱⁱ	3.018 (7)	N5···H3B^viii	2.94 (6)
O3···O1	3.092 (6)	N6···H8	2.6900
O3···O2	2.892 (7)	N7···H6Cⁱⁱⁱ	2.8700
O3···O4	2.781 (8)	N7···H3C	2.65 (7)
O3···O8ⁱⁱ	2.810 (8)	N7···H6B^iv	2.7000
O3···N7	3.243 (8)	N8···H1^vi	2.8800
O3···N3ⁱⁱ	3.193 (8)	N8···H3E	2.7100
O4···O3	2.781 (8)	C1···O9^x	3.199 (9)
O4···C8^iv	3.298 (7)	C1···O8^x	3.292 (8)
O4···N6ⁱⁱⁱ	3.233 (7)	C2···O9^x	3.244 (8)
O4···O2ⁱⁱⁱ	3.095 (6)	C3···O6	3.213 (9)
O4···N6^iv	2.913 (7)	C3···O7	3.227 (8)
O5···C7^v	3.362 (8)	C3···C4^vii	3.580 (9)
O5···N6ⁱⁱⁱ	3.231 (8)	C3···C3^vii	3.299 (9)
O5···N3ⁱⁱ	3.163 (8)	C4···C3^vii	3.580 (9)
O5···O1ⁱⁱ	3.148 (7)	C4···O6	3.294 (8)
O5···O3	3.087 (8)	C4···N7	3.383 (8)
O6···N6^iv	3.117 (7)	C6···N2^vii	3.392 (8)
O6···C4	3.294 (8)	C6···O6^xi	3.295 (8)
O6···C3	3.213 (9)	C7···O5^xi	3.362 (8)
O6···C6^v	3.295 (8)	C8···N8^xi	3.323 (8)
O7···C3	3.227 (8)	C8···O9^vii	3.059 (8)
O7···N3	2.937 (8)	C8···O8^xi	3.378 (8)
O8···C8^v	3.378 (8)	C8···O4^ix	3.298 (7)
O8···C1^vi	3.292 (8)	C9···N8^xi	3.406 (8)
O8···N3	3.148 (8)	C9···O9^vii	3.096 (9)
O8···O3ⁱⁱ	2.810 (8)	C10···O9^vii	3.271 (10)
O9···C9^vii	3.096 (9)	C3···H3E	2.6500
O9···C2^vi	3.244 (8)	C8···H6B	2.6300
O9···C8^vii	3.059 (8)	H1···O8^x	2.3900
O9···C1^vi	3.199 (9)	H1···O9^x	2.6000
O9···C10^vii	3.271 (10)	H1···N8^x	2.8800
O1···H7ⁱ	2.3600	H2···O9^x	2.6900
O2···H3Cⁱⁱⁱ	2.62 (7)	H3···N3	2.6900
O2···H3Bⁱⁱⁱ	2.82 (6)	H3···H3E	2.1300
O2···H8ⁱ	2.6900	H3···O7	2.3100
O3···H3Dⁱⁱ	2.5000	H3B···O2ⁱⁱⁱ	2.82 (6)
O4···H3C	2.06 (7)	H3B···H3Dⁱⁱ	2.3300
O4···H6Cⁱⁱⁱ	2.7200	H3B···O8ⁱⁱ	2.05 (7)
O4···H6B^iv	2.0700	H3B···N3ⁱⁱ	2.92 (6)
O4···H8^iv	2.3900	H3C···O5	2.66 (7)
O5···H3C	2.66 (7)	H3C···O4	2.06 (7)
O5···H6Cⁱⁱⁱ	2.4100	H3C···N7	2.65 (7)
O5···H7^v	2.4900	H3C···O2ⁱⁱⁱ	2.62 (7)
O5···H3Dⁱⁱ	2.4200	H3D···Zn1ⁱⁱ	3.5800
O6···H6^v	2.6000	H3D···H3Bⁱⁱ	2.3300
O6···H6B^iv	2.6500	H3D···O3ⁱⁱ	2.5000
O7···H3	2.3100	H3D···O5ⁱⁱ	2.4200
O7···H3E	2.0800	H3E···O7	2.0800
O8···H3E	2.6300	H3E···O8	2.6300
O8···H1^vi	2.3900	H3E···N8	2.7100
O8···H3Bⁱⁱ	2.05 (7)	H3E···C3	2.6500
O9···H2^vi	2.6900	H3E···H3	2.1300
O9···H1^vi	2.6000	H6···N2^vii	2.8100
N1···C5	2.382 (7)	H6···O6^xi	2.6000
N1···O1	2.627 (6)	H6B···O6^ix	2.6500
N1···N2	2.772 (8)	H6B···O4^ix	2.0700
N1···N4	3.094 (7)	H6B···N7^ix	2.7000
N1···O3	3.113 (8)	H6B···H8	2.1300
N2···N1	2.772 (8)	H6B···C8	2.6300
N2···C6^vii	3.392 (8)	H6C···O5ⁱⁱⁱ	2.4100
N3···O5ⁱⁱ	3.163 (8)	H6C···O4ⁱⁱⁱ	2.7200
N3···O7	2.937 (8)	H6C···N7ⁱⁱⁱ	2.8700
N3···O3ⁱⁱ	3.193 (8)	H7···O5^xi	2.4900
N3···O8	3.148 (8)	H7···O1^viii	2.3600
N4···N1	3.094 (7)	H8···O4^ix	2.3900
N4···O1	3.192 (6)	H8···O2^viii	2.6900
N4···O2	2.629 (6)	H8···N6	2.6900
N4···N5	2.766 (7)	H8···H6B	2.1300

O1—Zn1—O2	172.71 (15)	O4—N7—O5	117.5 (6)
O1—Zn1—O3	97.70 (18)	O4—N7—O6	119.2 (6)
O1—Zn1—N1	76.42 (15)	O5—N7—O6	123.3 (6)
O1—Zn1—N4	97.09 (15)	O8—N8—O9	119.1 (6)
O1—Zn1—N5ⁱ	86.43 (15)	O7—N8—O8	120.0 (6)
O2—Zn1—O3	89.28 (18)	O7—N8—O9	120.8 (6)
O2—Zn1—N1	100.98 (15)	N1—C1—C2	121.0 (6)
O2—Zn1—N4	76.01 (15)	N2—C2—C1	121.9 (6)
O2—Zn1—N5ⁱ	95.71 (15)	N2—C3—C4	122.8 (6)
O3—Zn1—N1	94.9 (2)	C3—C4—C5	125.3 (5)
O3—Zn1—N4	165.13 (19)	N1—C4—C5	115.2 (5)
O3—Zn1—N5ⁱ	90.0 (2)	N1—C4—C3	119.5 (5)
N1—Zn1—N4	90.03 (18)	O1—C5—C4	117.5 (5)
N1—Zn1—N5ⁱ	162.62 (16)	O1—C5—N3	121.7 (5)
N4—Zn1—N5ⁱ	89.34 (18)	N3—C5—C4	120.8 (5)
Zn1—O1—C5	118.7 (3)	N4—C6—C7	121.4 (5)
Zn1—O2—C10	118.8 (3)	N5—C7—C6	121.0 (5)
H3B—O3—H3C	112 (8)	N5—C8—C9	122.1 (5)
Zn1—O3—H3C	123 (6)	C8—C9—C10	126.0 (5)
Zn1—O3—H3B	126 (5)	N4—C9—C10	113.8 (5)
C1—N1—C4	118.4 (5)	N4—C9—C8	120.2 (5)
Zn1—N1—C4	112.1 (4)	O2—C10—C9	118.0 (5)
Zn1—N1—C1	129.4 (4)	N6—C10—C9	119.2 (5)
C2—N2—C3	116.3 (6)	O2—C10—N6	122.8 (5)
Zn1—N4—C6	128.9 (4)	C2—C1—H1	120.00
Zn1—N4—C9	113.0 (3)	N1—C1—H1	119.00
C6—N4—C9	118.1 (5)	N2—C2—H2	119.00
Zn1^viii—N5—C8	120.9 (4)	C1—C2—H2	119.00
C7—N5—C8	117.3 (5)	N2—C3—H3	119.00
Zn1^viii—N5—C7	121.8 (4)	C4—C3—H3	119.00
C5—N3—H3E	120.00	C7—C6—H6	119.00
H3D—N3—H3E	120.00	N4—C6—H6	119.00
C5—N3—H3D	120.00	N5—C7—H7	120.00
C10—N6—H6B	120.00	C6—C7—H7	119.00
C10—N6—H6C	120.00	C9—C8—H8	119.00
H6B—N6—H6C	120.00	N5—C8—H8	119.00

O3—Zn1—O1—C5	−92.4 (4)	Zn1—O2—C10—N6	170.5 (4)
N1—Zn1—O1—C5	0.9 (4)	Zn1—O2—C10—C9	−8.1 (6)
N4—Zn1—O1—C5	89.2 (4)	Zn1—N1—C4—C5	−2.1 (6)
N5ⁱ—Zn1—O1—C5	178.1 (4)	C1—N1—C4—C3	−1.8 (8)
O3—Zn1—O2—C10	−171.7 (4)	C4—N1—C1—C2	3.0 (9)
N1—Zn1—O2—C10	93.4 (4)	Zn1—N1—C4—C3	176.1 (4)
N4—Zn1—O2—C10	6.2 (4)	Zn1—N1—C1—C2	−174.5 (5)
N5ⁱ—Zn1—O2—C10	−81.7 (4)	C1—N1—C4—C5	−180.0 (5)
O1—Zn1—N1—C1	178.4 (6)	C2—N2—C3—C4	1.9 (10)
O2—Zn1—N1—C1	5.4 (6)	C3—N2—C2—C1	−0.8 (10)
O3—Zn1—N1—C1	−84.9 (5)	Zn1—N4—C9—C8	−179.9 (4)
N4—Zn1—N1—C1	81.1 (5)	Zn1—N4—C6—C7	−178.8 (5)
O1—Zn1—N1—C4	0.8 (4)	C6—N4—C9—C10	−180.0 (5)
O2—Zn1—N1—C4	−172.3 (4)	Zn1—N4—C9—C10	0.3 (6)
O3—Zn1—N1—C4	97.5 (4)	C6—N4—C9—C8	−0.1 (8)
N4—Zn1—N1—C4	−96.5 (4)	C9—N4—C6—C7	1.6 (9)
O1—Zn1—N4—C6	−0.4 (5)	C8—N5—C7—C6	1.0 (9)
O2—Zn1—N4—C6	177.3 (6)	Zn1^viii—N5—C7—C6	177.2 (5)
N1—Zn1—N4—C6	76.0 (5)	Zn1^viii—N5—C8—C9	−175.8 (4)
N5ⁱ—Zn1—N4—C6	−86.7 (5)	C7—N5—C8—C9	0.4 (8)
O1—Zn1—N4—C9	179.3 (4)	N1—C1—C2—N2	−1.7 (11)
O2—Zn1—N4—C9	−3.0 (4)	N2—C3—C4—C5	177.3 (6)
N1—Zn1—N4—C9	−104.3 (4)	N2—C3—C4—N1	−0.7 (9)
N5ⁱ—Zn1—N4—C9	93.0 (4)	N1—C4—C5—N3	−178.8 (5)
O1^viii—Zn1^viii—N5—C7	14.9 (5)	N1—C4—C5—O1	3.0 (7)
O2^viii—Zn1^viii—N5—C7	−158.1 (5)	C3—C4—C5—N3	3.2 (9)
O3^viii—Zn1^viii—N5—C7	112.6 (5)	C3—C4—C5—O1	−175.1 (5)
N4^viii—Zn1^viii—N5—C7	−82.2 (5)	N4—C6—C7—N5	−2.1 (10)
O1^viii—Zn1^viii—N5—C8	−169.1 (4)	N5—C8—C9—N4	−0.9 (8)
O2^viii—Zn1^viii—N5—C8	17.9 (4)	N5—C8—C9—C10	178.9 (5)
O3^viii—Zn1^viii—N5—C8	−71.4 (4)	N4—C9—C10—O2	5.0 (7)
N4^viii—Zn1^viii—N5—C8	93.8 (4)	C8—C9—C10—N6	6.5 (8)
Zn1—O1—C5—N3	179.4 (4)	N4—C9—C10—N6	−173.6 (5)
Zn1—O1—C5—C4	−2.3 (6)	C8—C9—C10—O2	−174.9 (5)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+1, −z+1; (iv) −x+2, y−1/2, −z+1/2; (v) −x+1, y−1/2, −z+1/2; (vi) x−1, y, z; (vii) −x+1, −y+1, −z; (viii) x, −y+3/2, z−1/2; (ix) −x+2, y+1/2, −z+1/2; (x) x+1, y, z; (xi) −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
O3—H3B···O8ⁱⁱ	0.76 (7)	2.05 (7)	2.810 (8)	177 (7)
O3—H3C···O4	0.75 (6)	2.06 (7)	2.781 (8)	162 (9)
N3—H3D···O3ⁱⁱ	0.86	2.50	3.193 (8)	138
N3—H3D···O5ⁱⁱ	0.86	2.42	3.163 (8)	144
N3—H3E···O7	0.86	2.08	2.937 (8)	172
N6—H6B···O4^ix	0.86	2.07	2.913 (7)	166
N6—H6C···O5ⁱⁱⁱ	0.86	2.41	3.231 (8)	161
C1—H1···O8^x	0.93	2.39	3.292 (8)	162
C3—H3···O7	0.93	2.31	3.227 (8)	169
C6—H6···O6^xi	0.93	2.60	3.295 (8)	132
C7—H7···O5^xi	0.93	2.49	3.362 (8)	156
C8—H8···O4^ix	0.93	2.39	3.298 (7)	167

Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+1, −z+1; (ix) −x+2, y+1/2, −z+1/2; (x) x+1, y, z; (xi) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Zn(C₅H₅N₃O)₂(H₂O)](NO₃)₂
M_r	453.67
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.4889 (11), 15.7477 (16), 9.9332 (10)
β (°)	97.664 (8)
V (Å³)	1626.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.58
Crystal size (mm)	0.23 × 0.12 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.070, 0.240
No. of measured, independent and observed [I > 2σ(I)] reflections	9288, 3192, 2088
R_int	0.123
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.076, 0.103, 1.06
No. of reflections	3192
No. of parameters	261
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.52

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Zn1—O1	2.064 (3)	Zn1—N1	2.180 (5)
Zn1—O2	2.073 (3)	Zn1—N4	2.193 (5)
Zn1—O3	2.042 (6)	Zn1—N5ⁱ	2.179 (5)

Symmetry code: (i) x, −y+3/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O8ⁱⁱ	0.76 (7)	2.05 (7)	2.810 (8)	177 (7)
O3—H3C···O4	0.75 (6)	2.06 (7)	2.781 (8)	162 (9)
N3—H3D···O3ⁱⁱ	0.86	2.5000	3.193 (8)	138
N3—H3D···O5ⁱⁱ	0.86	2.4200	3.163 (8)	144
N3—H3E···O7	0.86	2.0800	2.937 (8)	172
N6—H6B···O4ⁱⁱⁱ	0.86	2.0700	2.913 (7)	166
N6—H6C···O5^iv	0.86	2.4100	3.231 (8)	161
C1—H1···O8^v	0.93	2.3900	3.292 (8)	162
C3—H3···O7	0.93	2.3100	3.227 (8)	169
C6—H6···O6^vi	0.93	2.6000	3.295 (8)	132
C7—H7···O5^vi	0.93	2.4900	3.362 (8)	156
C8—H8···O4ⁱⁱⁱ	0.93	2.3900	3.298 (7)	167

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

Acknowledgements

We are grateful to the Islamic Azad University, Omidieh Branch for financial support.

References

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