catena-Poly[diacridinium [zinc(II)-di-μ-pyrazine-2,3-dicarboxyl­ato-κ3N1,O2:O3;O3:N1,O2]]

Eshtiagh-Hosseini, H.; Aghabozorg, H.; Mirzaei, M.

doi:10.1107/S1600536810025195

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m882

https://doi.org/10.1107/S1600536810025195

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catena-Poly[diacridinium [zinc(II)-di-μ-pyrazine-2,3-dicarboxylato-κ³N¹,O²:O³;O³:N¹,O²]]

Hossein Eshtiagh-Hosseini,^a ^* Hossein Aghabozorg ^b and Masoud Mirzaei ^a

^aDepartment of Chemistry, School of Sciences, Ferdowsi University of Mashhad, Mashhad, Iran, and ^bFaculty of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran
^*Correspondence e-mail: heshtiagh@ferdowsi.um.ac.ir

(Received 12 June 2010; accepted 27 June 2010; online 3 July 2010)

The crystal structure of the title compound, {(C₁₃H₁₀N)₂[Zn(C₆H₂N₂O₄)₂]}_n, consists of polymeric Zn complex anions and discrete acridinium cations. The Zn cation, located on an inversion center, is N,O-chelated by two pyrazine-2,3-dicarboxylate (pyzdc) anions in the basal plane, and is further coordinated by two carboxylate O atoms from adjacent pyzdc anions in the axial directions with a longer Zn—O bond distance, forming a distorted ZnN₂O₄ coordination geometry. The pyzdc anions bridge the Zn cations, forming polymeric chains running along the crystallographic b axis. The acridinium cations are linked to the complex chains via N—H⋯O and C—H⋯O hydrogen bonding. Significant π–π stacking between parallel acridinium ring systems is observed in the crystal structure, face-to-face distances being 3.311 (3) and 3.267 (4) Å.

Related literature

For the structure of a related Co(II) complex with pyzdc ligands, see: Aghabozorg et al. (2010b ). For the proton transfer of the carboxyl group, see: Aghabozorg et al. (2010a ).

Experimental

Crystal data

(C₁₃H₁₀N)₂[Zn(C₆H₂N₂O₄)₂]
M_r = 758.00
Monoclinic, P 2₁ /c
a = 13.2256 (12) Å
b = 6.8141 (6) Å
c = 17.9889 (16) Å
β = 111.013 (2)°
V = 1513.4 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.88 mm⁻¹
T = 120 K
0.27 × 0.15 × 0.13 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick 1998 ) T_min = 0.845, T_max = 0.891
15968 measured reflections
2720 independent reflections
2292 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.115
S = 1.14
2720 reflections
244 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O1	2.0326 (17)
Zn1—N1	2.093 (2)
Zn1—O4ⁱ	2.2435 (17)
Symmetry code: (i) x, y+1, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O3	0.86 (2)	1.78 (2)	2.634 (3)	172 (3)
C13—H13⋯O2ⁱⁱ	0.93	2.38	3.211 (4)	149
C16—H16⋯O3ⁱⁱⁱ	0.93	2.49	3.377 (3)	159
Symmetry codes: (ii) -x+1, -y+1, -z+1; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; 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: https://doi.org/10.1107/S1600536810025195/xu2784sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810025195/xu2784Isup2.hkl

checkCIF report

Comment top

H₂pyzdc has proved to be well suited for the construction of multidimensional frameworks due to the presence of two adjacent carboxylate groups (O donor atoms) as substituents on the N-heterocyclic pyrazine ring (N donor atoms). In this paper, we report the hydrothermal synthesis, crystal and molecular structure of a pyrazinecarboxylate-based Zn atom supramolecular coordination compound as a novel inorganic polymer, for the first time. The hydrothermal reaction between H₂pyzdc, acr, and zinc nitrate tetra-hydrate, resulted in the formation of {(C₁₃H₁₀N)₂[Zn(C₆H₂N₂O₄)₂]}_n. This inorganic polymeric compound consists of an anionic complex, [Zn(pyzdc)₂]^2–, counter-ions, (acrH)⁺ molecules. In the title inorganic polymeric compound, two COOH protons have been transferred to non-coordinated pyridine rings of acr moieties. The central Zn1 atom is six-coordinated by N1 and O1 atoms in the equatorial plane from two (pyzdc)^2– ligands and by two O4 atoms in the axial positions (Fig. 1). The coordination environment around the Zn atom may be considered as slightly distorted octahedral. The anionic complex lies on a crystallographic center of symmetry. The mean Zn–N and Zn–O bond lengths are 2.093 (2) and 2.138 (17) Å, respectively. In the structure of the title inorganic polymeric compound, (acrH)⁺ cations and [Zn(pyzdc)₂]^2- anions are linked together by classical N3–H3B···O3 and non-classical C13–H13···O2 and C16–H16···O3 hydrogen bonds. In the crystal structure of the title polymeric compound, the spaces between [Zn(pyzdc)₂]^2- fragments are filled with layers of (acrH)⁺ cations. Indeed, the arrangement of anionic layers to each other resulted in the making of suitable spaces for entering cationic parts. As a essential factor extensive π–π stacking interactions between parallel aromatic rings of the acridinium ions,(acrH)⁺, with face-to-face distances of 3.311 (3) and 3.267 (4) Å, caused to further stabilization of crystalline network.

It should be noted that most of the molecular structures consisting up dicarboxylate ligands incorporate water molecules of hydration which may lead to formation kind of (H₂O)_n clusters (Review article by Aghabozorg et al. 2010a). The used reaction conditions such as hydrothermal synthesis versus just normal synthesis in aqueous conditions play basic roles in this regard. Additionally, if water molecules are present, it may prevent polymerization because it will coordinate to the metal center and so, used dicarboxylate ligand can not play chelate role for connecting metal centers to each other. For example, herein, we have obtained an inorganic polymer because of applying hydrothermal condition. But, recently published work of our research group (Aghabozorg et al. 2010b) show that the reaction of cobalt(II) nitrate hexa-hydrate, acr, and H₂pyzdc in aqueous solution and routine condition resulted in the formation of (acrH)₂[Co(pyzdc)₂(H₂O)₂]. 6H₂O crystals as monomeric structure.

Related literature top

For structure of a related Co(II) complex with pyzdc ligands, see: Aghabozorg et al. (2010b). For the proton transfer of the carboxyl group, see: Aghabozorg et al. (2010a).

Experimental top

A mixture of H₂pyzdc (0.83 mmol, 140 mg), acridine (1.67 mmol, 300 mg), and Zn(NO₃)₂.4H₂O (0.27 mmol, 80 mg) in distilled water (12 ml) was placed in a Teflon-lined stainless steel vessel, heated to 423 K for 4 days, and then cooled to room temperature over 12 h. Red block crystals were obtained after five months by slow evaporation of solvent with a yield of approximate 55% based on Zn.

Structure description top

For structure of a related Co(II) complex with pyzdc ligands, see: Aghabozorg et al. (2010b). For the proton transfer of the carboxyl group, see: Aghabozorg et al. (2010a).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); 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. A part of the title polymeric compound, thermal ellipsoids are shown at the 50% probability level. Symmetry code: (i): 2-x, 2-y, 1-z; (ii): x, 1+y, z; (iii): 2-x, 1-y, 1-z.

catena-Poly[diacridinium [zinc(II)-di-µ-pyrazine-2,3-dicarboxylato- κ³N¹,O²:O³;O³:N¹,O²]] top

Crystal data top

(C₁₃H₁₀N)₂[Zn(C₆H₂N₂O₄)₂]	F(000) = 776
M_r = 758.00	D_x = 1.663 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 600 reflections
a = 13.2256 (12) Å	θ = 2.0–24.0°
b = 6.8141 (6) Å	µ = 0.88 mm⁻¹
c = 17.9889 (16) Å	T = 120 K
β = 111.013 (2)°	Prism, red
V = 1513.4 (2) Å³	0.27 × 0.15 × 0.13 mm
Z = 2

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2720 independent reflections
Radiation source: fine-focus sealed tube	2292 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scans	θ_max = 25.2°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick 1998)	h = −15→15
T_min = 0.845, T_max = 0.891	k = −8→8
15968 measured reflections	l = −21→21

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ²(F_o²) + (0.0644P)² + 1.454P] where P = (F_o² + 2F_c²)/3
2720 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.76 e Å⁻³
1 restraint	Δρ_min = −0.47 e Å⁻³

Crystal data top

(C₁₃H₁₀N)₂[Zn(C₆H₂N₂O₄)₂]	V = 1513.4 (2) Å³
M_r = 758.00	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.2256 (12) Å	µ = 0.88 mm⁻¹
b = 6.8141 (6) Å	T = 120 K
c = 17.9889 (16) Å	0.27 × 0.15 × 0.13 mm
β = 111.013 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2720 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick 1998)	2292 reflections with I > 2σ(I)
T_min = 0.845, T_max = 0.891	R_int = 0.032
15968 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	1 restraint
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	Δρ_max = 0.76 e Å⁻³
2720 reflections	Δρ_min = −0.47 e Å⁻³
244 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
Zn1	1.0000	1.0000	0.5000	0.02299 (17)
N1	0.97579 (16)	0.7741 (3)	0.41650 (12)	0.0181 (4)
N2	0.92414 (17)	0.4493 (3)	0.31697 (13)	0.0235 (5)
N3	0.56207 (16)	0.2835 (3)	0.40993 (12)	0.0188 (4)
O1	0.90033 (14)	0.8249 (3)	0.53444 (11)	0.0225 (4)
O2	0.81853 (16)	0.5307 (3)	0.51045 (12)	0.0275 (5)
O3	0.71207 (14)	0.3430 (3)	0.34784 (11)	0.0231 (4)
O4	0.84996 (14)	0.1517 (3)	0.41985 (10)	0.0219 (4)
C1	0.87279 (19)	0.6642 (4)	0.49636 (15)	0.0183 (5)
C2	0.91244 (18)	0.6323 (4)	0.42725 (14)	0.0166 (5)
C3	1.0143 (2)	0.7552 (4)	0.35783 (15)	0.0213 (5)
H3	1.0591	0.8517	0.3499	0.026*
C4	0.9879 (2)	0.5930 (4)	0.30892 (15)	0.0234 (6)
H4	1.0158	0.5833	0.2684	0.028*
C5	0.88694 (19)	0.4691 (4)	0.37672 (15)	0.0174 (5)
C6	0.8114 (2)	0.3068 (4)	0.38376 (15)	0.0197 (5)
C7	0.4615 (2)	0.3287 (3)	0.35817 (15)	0.0173 (5)
C8	0.4441 (2)	0.3677 (4)	0.27753 (15)	0.0216 (5)
H8	0.5016	0.3642	0.2593	0.026*
C9	0.3419 (2)	0.4107 (4)	0.22648 (16)	0.0233 (6)
H9	0.3300	0.4348	0.1731	0.028*
C10	0.2537 (2)	0.4193 (4)	0.25332 (15)	0.0233 (6)
H10	0.1850	0.4504	0.2176	0.028*
C11	0.2682 (2)	0.3826 (4)	0.33062 (16)	0.0229 (6)
H11	0.2095	0.3882	0.3475	0.027*
C12	0.3732 (2)	0.3354 (4)	0.38588 (15)	0.0187 (5)
C13	0.3932 (2)	0.2948 (3)	0.46547 (15)	0.0183 (5)
H13	0.3366	0.3014	0.4846	0.022*
C14	0.4961 (2)	0.2445 (4)	0.51706 (15)	0.0183 (5)
C15	0.5195 (2)	0.1983 (4)	0.59890 (15)	0.0219 (6)
H15	0.4644	0.2036	0.6196	0.026*
C16	0.6211 (2)	0.1467 (4)	0.64685 (16)	0.0239 (6)
H16	0.6358	0.1182	0.7003	0.029*
C17	0.7049 (2)	0.1364 (4)	0.61494 (16)	0.0237 (6)
H17	0.7738	0.0977	0.6480	0.028*
C18	0.6877 (2)	0.1814 (4)	0.53774 (15)	0.0210 (5)
H18	0.7441	0.1759	0.5184	0.025*
C19	0.5823 (2)	0.2368 (3)	0.48739 (14)	0.0180 (5)
H3N	0.6133 (15)	0.292 (4)	0.3912 (15)	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0244 (3)	0.0228 (3)	0.0256 (3)	−0.00764 (17)	0.0137 (2)	−0.00581 (17)
N1	0.0126 (10)	0.0220 (11)	0.0196 (10)	0.0012 (8)	0.0058 (8)	0.0009 (9)
N2	0.0187 (11)	0.0312 (12)	0.0221 (11)	−0.0029 (9)	0.0093 (9)	−0.0022 (9)
N3	0.0152 (11)	0.0215 (11)	0.0217 (11)	−0.0001 (8)	0.0090 (9)	0.0011 (9)
O1	0.0224 (9)	0.0225 (9)	0.0252 (10)	−0.0031 (7)	0.0118 (8)	−0.0029 (7)
O2	0.0303 (11)	0.0281 (10)	0.0318 (11)	−0.0089 (8)	0.0205 (9)	−0.0043 (8)
O3	0.0149 (9)	0.0282 (10)	0.0251 (10)	−0.0018 (7)	0.0058 (8)	0.0009 (8)
O4	0.0209 (9)	0.0198 (9)	0.0234 (9)	−0.0017 (7)	0.0059 (8)	−0.0002 (7)
C1	0.0142 (12)	0.0211 (13)	0.0193 (13)	0.0010 (10)	0.0058 (10)	0.0012 (10)
C2	0.0120 (11)	0.0199 (12)	0.0177 (12)	0.0017 (9)	0.0051 (10)	0.0034 (10)
C3	0.0131 (12)	0.0285 (13)	0.0226 (13)	−0.0016 (10)	0.0067 (10)	0.0028 (11)
C4	0.0181 (13)	0.0320 (15)	0.0226 (13)	0.0014 (11)	0.0102 (11)	−0.0014 (11)
C5	0.0109 (11)	0.0223 (12)	0.0177 (12)	0.0004 (9)	0.0035 (10)	0.0003 (10)
C6	0.0164 (12)	0.0248 (13)	0.0182 (12)	−0.0031 (10)	0.0065 (10)	−0.0050 (10)
C7	0.0161 (12)	0.0150 (11)	0.0207 (13)	−0.0002 (9)	0.0064 (10)	−0.0015 (9)
C8	0.0201 (13)	0.0250 (13)	0.0226 (13)	0.0016 (10)	0.0110 (11)	0.0003 (11)
C9	0.0267 (14)	0.0232 (13)	0.0186 (13)	0.0004 (11)	0.0066 (11)	−0.0013 (10)
C10	0.0156 (13)	0.0259 (13)	0.0233 (14)	0.0011 (10)	0.0009 (11)	0.0021 (11)
C11	0.0149 (12)	0.0256 (13)	0.0284 (14)	−0.0010 (10)	0.0081 (11)	0.0008 (11)
C12	0.0165 (12)	0.0188 (12)	0.0224 (13)	−0.0008 (9)	0.0088 (11)	−0.0016 (10)
C13	0.0165 (12)	0.0187 (12)	0.0231 (13)	−0.0027 (10)	0.0112 (10)	−0.0028 (10)
C14	0.0177 (12)	0.0158 (12)	0.0223 (13)	−0.0035 (9)	0.0083 (10)	−0.0022 (10)
C15	0.0233 (13)	0.0232 (13)	0.0231 (13)	−0.0040 (11)	0.0131 (11)	−0.0009 (10)
C16	0.0250 (14)	0.0257 (13)	0.0203 (13)	−0.0065 (11)	0.0073 (11)	0.0017 (10)
C17	0.0164 (13)	0.0265 (13)	0.0247 (14)	−0.0015 (10)	0.0032 (11)	0.0050 (11)
C18	0.0152 (12)	0.0232 (13)	0.0252 (14)	−0.0020 (10)	0.0080 (11)	0.0010 (10)
C19	0.0194 (13)	0.0163 (11)	0.0199 (12)	−0.0032 (10)	0.0090 (10)	0.0000 (10)

Geometric parameters (Å, º) top

Zn1—O1	2.0326 (17)	C7—C8	1.410 (4)
Zn1—O1ⁱ	2.0326 (17)	C7—C12	1.425 (3)
Zn1—N1ⁱ	2.093 (2)	C8—C9	1.366 (4)
Zn1—N1	2.093 (2)	C8—H8	0.9300
Zn1—O4ⁱⁱ	2.2435 (17)	C9—C10	1.414 (4)
Zn1—O4ⁱⁱⁱ	2.2435 (17)	C9—H9	0.9300
N1—C3	1.332 (3)	C10—C11	1.357 (4)
N1—C2	1.338 (3)	C10—H10	0.9300
N2—C4	1.333 (4)	C11—C12	1.425 (4)
N2—C5	1.340 (3)	C11—H11	0.9300
N3—C7	1.358 (3)	C12—C13	1.387 (4)
N3—C19	1.359 (3)	C13—C14	1.388 (4)
N3—H3N	0.86 (2)	C13—H13	0.9300
O1—C1	1.273 (3)	C14—C19	1.422 (3)
O2—C1	1.240 (3)	C14—C15	1.427 (4)
O3—C6	1.263 (3)	C15—C16	1.357 (4)
O4—C6	1.249 (3)	C15—H15	0.9300
C1—C2	1.528 (3)	C16—C17	1.422 (4)
C2—C5	1.399 (3)	C16—H16	0.9300
C3—C4	1.377 (4)	C17—C18	1.359 (4)
C3—H3	0.9300	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.414 (4)
C5—C6	1.526 (3)	C18—H18	0.9300

O1—Zn1—O1ⁱ	180.0	O3—C6—C5	114.1 (2)
O1—Zn1—N1ⁱ	99.32 (7)	N3—C7—C8	120.4 (2)
O1ⁱ—Zn1—N1ⁱ	80.68 (7)	N3—C7—C12	119.5 (2)
O1—Zn1—N1	80.68 (7)	C8—C7—C12	120.1 (2)
O1ⁱ—Zn1—N1	99.32 (7)	C9—C8—C7	119.3 (2)
N1ⁱ—Zn1—N1	180.0	C9—C8—H8	120.4
O1—Zn1—O4ⁱⁱ	86.88 (7)	C7—C8—H8	120.4
O1ⁱ—Zn1—O4ⁱⁱ	93.12 (7)	C8—C9—C10	121.2 (2)
N1ⁱ—Zn1—O4ⁱⁱ	89.71 (7)	C8—C9—H9	119.4
N1—Zn1—O4ⁱⁱ	90.29 (7)	C10—C9—H9	119.4
O1—Zn1—O4ⁱⁱⁱ	93.12 (7)	C11—C10—C9	120.8 (2)
O1ⁱ—Zn1—O4ⁱⁱⁱ	86.88 (7)	C11—C10—H10	119.6
N1ⁱ—Zn1—O4ⁱⁱⁱ	90.29 (7)	C9—C10—H10	119.6
N1—Zn1—O4ⁱⁱⁱ	89.71 (7)	C10—C11—C12	120.1 (2)
O4ⁱⁱ—Zn1—O4ⁱⁱⁱ	180.000 (1)	C10—C11—H11	120.0
C3—N1—C2	118.8 (2)	C12—C11—H11	120.0
C3—N1—Zn1	129.49 (17)	C13—C12—C11	122.9 (2)
C2—N1—Zn1	111.71 (16)	C13—C12—C7	118.5 (2)
C4—N2—C5	116.2 (2)	C11—C12—C7	118.6 (2)
C7—N3—C19	122.7 (2)	C12—C13—C14	121.2 (2)
C7—N3—H3N	115.6 (19)	C12—C13—H13	119.4
C19—N3—H3N	121.6 (19)	C14—C13—H13	119.4
C1—O1—Zn1	115.63 (15)	C13—C14—C19	119.0 (2)
C6—O4—Zn1^iv	145.70 (16)	C13—C14—C15	122.8 (2)
O2—C1—O1	126.6 (2)	C19—C14—C15	118.2 (2)
O2—C1—C2	117.0 (2)	C16—C15—C14	120.8 (2)
O1—C1—C2	116.4 (2)	C16—C15—H15	119.6
N1—C2—C5	119.9 (2)	C14—C15—H15	119.6
N1—C2—C1	115.5 (2)	C15—C16—C17	119.6 (2)
C5—C2—C1	124.7 (2)	C15—C16—H16	120.2
N1—C3—C4	120.1 (2)	C17—C16—H16	120.2
N1—C3—H3	119.9	C18—C17—C16	122.1 (2)
C4—C3—H3	119.9	C18—C17—H17	118.9
N2—C4—C3	123.1 (2)	C16—C17—H17	118.9
N2—C4—H4	118.5	C17—C18—C19	118.7 (2)
C3—C4—H4	118.5	C17—C18—H18	120.6
N2—C5—C2	121.9 (2)	C19—C18—H18	120.6
N2—C5—C6	115.7 (2)	N3—C19—C18	120.4 (2)
C2—C5—C6	122.3 (2)	N3—C19—C14	119.1 (2)
O4—C6—O3	126.0 (2)	C18—C19—C14	120.5 (2)
O4—C6—C5	119.9 (2)

O1—Zn1—N1—C3	179.3 (2)	N2—C5—C6—O4	83.9 (3)
O1ⁱ—Zn1—N1—C3	−0.7 (2)	C2—C5—C6—O4	−98.6 (3)
O4ⁱⁱ—Zn1—N1—C3	92.5 (2)	N2—C5—C6—O3	−93.2 (3)
O4ⁱⁱⁱ—Zn1—N1—C3	−87.5 (2)	C2—C5—C6—O3	84.3 (3)
O1—Zn1—N1—C2	−1.26 (16)	C19—N3—C7—C8	−177.2 (2)
O1ⁱ—Zn1—N1—C2	178.74 (16)	C19—N3—C7—C12	2.4 (4)
O4ⁱⁱ—Zn1—N1—C2	−88.05 (16)	N3—C7—C8—C9	179.3 (2)
O4ⁱⁱⁱ—Zn1—N1—C2	91.95 (16)	C12—C7—C8—C9	−0.4 (4)
N1ⁱ—Zn1—O1—C1	−177.15 (17)	C7—C8—C9—C10	0.8 (4)
N1—Zn1—O1—C1	2.85 (17)	C8—C9—C10—C11	−0.8 (4)
O4ⁱⁱ—Zn1—O1—C1	93.66 (17)	C9—C10—C11—C12	0.2 (4)
O4ⁱⁱⁱ—Zn1—O1—C1	−86.34 (17)	C10—C11—C12—C13	−179.4 (2)
Zn1—O1—C1—O2	175.2 (2)	C10—C11—C12—C7	0.2 (4)
Zn1—O1—C1—C2	−3.8 (3)	N3—C7—C12—C13	−0.1 (3)
C3—N1—C2—C5	−0.7 (3)	C8—C7—C12—C13	179.5 (2)
Zn1—N1—C2—C5	179.80 (17)	N3—C7—C12—C11	−179.8 (2)
C3—N1—C2—C1	179.3 (2)	C8—C7—C12—C11	−0.2 (3)
Zn1—N1—C2—C1	−0.2 (2)	C11—C12—C13—C14	178.3 (2)
O2—C1—C2—N1	−176.4 (2)	C7—C12—C13—C14	−1.4 (4)
O1—C1—C2—N1	2.7 (3)	C12—C13—C14—C19	0.7 (4)
O2—C1—C2—C5	3.6 (4)	C12—C13—C14—C15	−178.8 (2)
O1—C1—C2—C5	−177.4 (2)	C13—C14—C15—C16	178.9 (2)
C2—N1—C3—C4	0.7 (4)	C19—C14—C15—C16	−0.6 (4)
Zn1—N1—C3—C4	−179.85 (18)	C14—C15—C16—C17	−0.7 (4)
C5—N2—C4—C3	−0.7 (4)	C15—C16—C17—C18	1.6 (4)
N1—C3—C4—N2	0.0 (4)	C16—C17—C18—C19	−1.2 (4)
C4—N2—C5—C2	0.7 (4)	C7—N3—C19—C18	176.9 (2)
C4—N2—C5—C6	178.2 (2)	C7—N3—C19—C14	−3.1 (4)
N1—C2—C5—N2	−0.1 (4)	C17—C18—C19—N3	179.8 (2)
C1—C2—C5—N2	179.9 (2)	C17—C18—C19—C14	−0.2 (4)
N1—C2—C5—C6	−177.4 (2)	C13—C14—C19—N3	1.6 (3)
C1—C2—C5—C6	2.6 (4)	C15—C14—C19—N3	−178.9 (2)
Zn1^iv—O4—C6—O3	−171.95 (18)	C13—C14—C19—C18	−178.4 (2)
Zn1^iv—O4—C6—C5	11.3 (4)	C15—C14—C19—C18	1.1 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O3	0.86 (2)	1.78 (2)	2.634 (3)	172 (3)
C13—H13···O2^v	0.93	2.38	3.211 (4)	149
C16—H16···O3^vi	0.93	2.49	3.377 (3)	159

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

Experimental details

Crystal data
Chemical formula	(C₁₃H₁₀N)₂[Zn(C₆H₂N₂O₄)₂]
M_r	758.00
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	13.2256 (12), 6.8141 (6), 17.9889 (16)
β (°)	111.013 (2)
V (Å³)	1513.4 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.88
Crystal size (mm)	0.27 × 0.15 × 0.13

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick 1998)
T_min, T_max	0.845, 0.891
No. of measured, independent and observed [I > 2σ(I)] reflections	15968, 2720, 2292
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.115, 1.14
No. of reflections	2720
No. of parameters	244
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)	0.76, −0.47

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Zn1—O1	2.0326 (17)	Zn1—O4ⁱ	2.2435 (17)
Zn1—N1	2.093 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O3	0.86 (2)	1.78 (2)	2.634 (3)	172 (3)
C13—H13···O2ⁱⁱ	0.93	2.38	3.211 (4)	149
C16—H16···O3ⁱⁱⁱ	0.93	2.49	3.377 (3)	159

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

Acknowledgements

The Ferdowsi University of Mashhad is gratefully acknowledged for financial support.

References

Aghabozorg, H., Attar Gharamaleki, J., Parvizi, M. & Derikvand, Z. (2010b). Acta Cryst. E66, m83–m84. Web of Science CSD CrossRef IUCr Journals Google Scholar
Aghabozorg, H., Eshtiagh-Hosseini, H., Salimi, A. R. & Mirzaei, M. (2010a). J. Iran. Chem. Soc. 7, 289–300. CrossRef CAS Google Scholar
Bruker (1998). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1998). 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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