metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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 ππ 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[Aghabozorg, H., Attar Gharamaleki, J., Parvizi, M. & Derikvand, Z. (2010b). Acta Cryst. E66, m83-m84.]). For the proton transfer of the carboxyl group, see: Aghabozorg et al. (2010a[Aghabozorg, H., Eshtiagh-Hosseini, H., Salimi, A. R. & Mirzaei, M. (2010a). J. Iran. Chem. Soc. 7, 289-300.]).

[Scheme 1]

Experimental

Crystal data
  • (C13H10N)2[Zn(C6H2N2O4)2]

  • Mr = 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[Sheldrick, G. M. (1998). SADABS. University of Göttingen, Germany.]) Tmin = 0.845, Tmax = 0.891

  • 15968 measured reflections

  • 2720 independent reflections

  • 2292 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.76 e Å−3

  • Δρmin = −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 DA 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[Bruker (1998). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 1998[Bruker (1998). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


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 ππ 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.

Refinement top

N-bonded H atom was located in a difference Fourier map and refined with a distance restraint. Other H atoms were placed in calculated positions and refined in a riding mode. Uiso(H) = 1.2 Ueq(C,N).

Structure description 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 ππ 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.

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
[Figure 1] 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
Mr = 758.00Dx = 1.663 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 600 reflections
a = 13.2256 (12) Åθ = 2.0–24.0°
b = 6.8141 (6) ŵ = 0.88 mm1
c = 17.9889 (16) ÅT = 120 K
β = 111.013 (2)°Prism, red
V = 1513.4 (2) Å30.27 × 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 tube2292 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω scansθmax = 25.2°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick 1998)
h = 1515
Tmin = 0.845, Tmax = 0.891k = 88
15968 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.14 w = 1/[σ2(Fo2) + (0.0644P)2 + 1.454P]
where P = (Fo2 + 2Fc2)/3
2720 reflections(Δ/σ)max = 0.001
244 parametersΔρmax = 0.76 e Å3
1 restraintΔρmin = 0.47 e Å3
Crystal data top
(C13H10N)2[Zn(C6H2N2O4)2]V = 1513.4 (2) Å3
Mr = 758.00Z = 2
Monoclinic, P21/cMo Kα radiation
a = 13.2256 (12) ŵ = 0.88 mm1
b = 6.8141 (6) ÅT = 120 K
c = 17.9889 (16) Å0.27 × 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)
Tmin = 0.845, Tmax = 0.891Rint = 0.032
15968 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0421 restraint
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.14Δρmax = 0.76 e Å3
2720 reflectionsΔρmin = 0.47 e Å3
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
xyzUiso*/Ueq
Zn11.00001.00000.50000.02299 (17)
N10.97579 (16)0.7741 (3)0.41650 (12)0.0181 (4)
N20.92414 (17)0.4493 (3)0.31697 (13)0.0235 (5)
N30.56207 (16)0.2835 (3)0.40993 (12)0.0188 (4)
O10.90033 (14)0.8249 (3)0.53444 (11)0.0225 (4)
O20.81853 (16)0.5307 (3)0.51045 (12)0.0275 (5)
O30.71207 (14)0.3430 (3)0.34784 (11)0.0231 (4)
O40.84996 (14)0.1517 (3)0.41985 (10)0.0219 (4)
C10.87279 (19)0.6642 (4)0.49636 (15)0.0183 (5)
C20.91244 (18)0.6323 (4)0.42725 (14)0.0166 (5)
C31.0143 (2)0.7552 (4)0.35783 (15)0.0213 (5)
H31.05910.85170.34990.026*
C40.9879 (2)0.5930 (4)0.30892 (15)0.0234 (6)
H41.01580.58330.26840.028*
C50.88694 (19)0.4691 (4)0.37672 (15)0.0174 (5)
C60.8114 (2)0.3068 (4)0.38376 (15)0.0197 (5)
C70.4615 (2)0.3287 (3)0.35817 (15)0.0173 (5)
C80.4441 (2)0.3677 (4)0.27753 (15)0.0216 (5)
H80.50160.36420.25930.026*
C90.3419 (2)0.4107 (4)0.22648 (16)0.0233 (6)
H90.33000.43480.17310.028*
C100.2537 (2)0.4193 (4)0.25332 (15)0.0233 (6)
H100.18500.45040.21760.028*
C110.2682 (2)0.3826 (4)0.33062 (16)0.0229 (6)
H110.20950.38820.34750.027*
C120.3732 (2)0.3354 (4)0.38588 (15)0.0187 (5)
C130.3932 (2)0.2948 (3)0.46547 (15)0.0183 (5)
H130.33660.30140.48460.022*
C140.4961 (2)0.2445 (4)0.51706 (15)0.0183 (5)
C150.5195 (2)0.1983 (4)0.59890 (15)0.0219 (6)
H150.46440.20360.61960.026*
C160.6211 (2)0.1467 (4)0.64685 (16)0.0239 (6)
H160.63580.11820.70030.029*
C170.7049 (2)0.1364 (4)0.61494 (16)0.0237 (6)
H170.77380.09770.64800.028*
C180.6877 (2)0.1814 (4)0.53774 (15)0.0210 (5)
H180.74410.17590.51840.025*
C190.5823 (2)0.2368 (3)0.48739 (14)0.0180 (5)
H3N0.6133 (15)0.292 (4)0.3912 (15)0.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0244 (3)0.0228 (3)0.0256 (3)0.00764 (17)0.0137 (2)0.00581 (17)
N10.0126 (10)0.0220 (11)0.0196 (10)0.0012 (8)0.0058 (8)0.0009 (9)
N20.0187 (11)0.0312 (12)0.0221 (11)0.0029 (9)0.0093 (9)0.0022 (9)
N30.0152 (11)0.0215 (11)0.0217 (11)0.0001 (8)0.0090 (9)0.0011 (9)
O10.0224 (9)0.0225 (9)0.0252 (10)0.0031 (7)0.0118 (8)0.0029 (7)
O20.0303 (11)0.0281 (10)0.0318 (11)0.0089 (8)0.0205 (9)0.0043 (8)
O30.0149 (9)0.0282 (10)0.0251 (10)0.0018 (7)0.0058 (8)0.0009 (8)
O40.0209 (9)0.0198 (9)0.0234 (9)0.0017 (7)0.0059 (8)0.0002 (7)
C10.0142 (12)0.0211 (13)0.0193 (13)0.0010 (10)0.0058 (10)0.0012 (10)
C20.0120 (11)0.0199 (12)0.0177 (12)0.0017 (9)0.0051 (10)0.0034 (10)
C30.0131 (12)0.0285 (13)0.0226 (13)0.0016 (10)0.0067 (10)0.0028 (11)
C40.0181 (13)0.0320 (15)0.0226 (13)0.0014 (11)0.0102 (11)0.0014 (11)
C50.0109 (11)0.0223 (12)0.0177 (12)0.0004 (9)0.0035 (10)0.0003 (10)
C60.0164 (12)0.0248 (13)0.0182 (12)0.0031 (10)0.0065 (10)0.0050 (10)
C70.0161 (12)0.0150 (11)0.0207 (13)0.0002 (9)0.0064 (10)0.0015 (9)
C80.0201 (13)0.0250 (13)0.0226 (13)0.0016 (10)0.0110 (11)0.0003 (11)
C90.0267 (14)0.0232 (13)0.0186 (13)0.0004 (11)0.0066 (11)0.0013 (10)
C100.0156 (13)0.0259 (13)0.0233 (14)0.0011 (10)0.0009 (11)0.0021 (11)
C110.0149 (12)0.0256 (13)0.0284 (14)0.0010 (10)0.0081 (11)0.0008 (11)
C120.0165 (12)0.0188 (12)0.0224 (13)0.0008 (9)0.0088 (11)0.0016 (10)
C130.0165 (12)0.0187 (12)0.0231 (13)0.0027 (10)0.0112 (10)0.0028 (10)
C140.0177 (12)0.0158 (12)0.0223 (13)0.0035 (9)0.0083 (10)0.0022 (10)
C150.0233 (13)0.0232 (13)0.0231 (13)0.0040 (11)0.0131 (11)0.0009 (10)
C160.0250 (14)0.0257 (13)0.0203 (13)0.0065 (11)0.0073 (11)0.0017 (10)
C170.0164 (13)0.0265 (13)0.0247 (14)0.0015 (10)0.0032 (11)0.0050 (11)
C180.0152 (12)0.0232 (13)0.0252 (14)0.0020 (10)0.0080 (11)0.0010 (10)
C190.0194 (13)0.0163 (11)0.0199 (12)0.0032 (10)0.0090 (10)0.0000 (10)
Geometric parameters (Å, º) top
Zn1—O12.0326 (17)C7—C81.410 (4)
Zn1—O1i2.0326 (17)C7—C121.425 (3)
Zn1—N1i2.093 (2)C8—C91.366 (4)
Zn1—N12.093 (2)C8—H80.9300
Zn1—O4ii2.2435 (17)C9—C101.414 (4)
Zn1—O4iii2.2435 (17)C9—H90.9300
N1—C31.332 (3)C10—C111.357 (4)
N1—C21.338 (3)C10—H100.9300
N2—C41.333 (4)C11—C121.425 (4)
N2—C51.340 (3)C11—H110.9300
N3—C71.358 (3)C12—C131.387 (4)
N3—C191.359 (3)C13—C141.388 (4)
N3—H3N0.86 (2)C13—H130.9300
O1—C11.273 (3)C14—C191.422 (3)
O2—C11.240 (3)C14—C151.427 (4)
O3—C61.263 (3)C15—C161.357 (4)
O4—C61.249 (3)C15—H150.9300
C1—C21.528 (3)C16—C171.422 (4)
C2—C51.399 (3)C16—H160.9300
C3—C41.377 (4)C17—C181.359 (4)
C3—H30.9300C17—H170.9300
C4—H40.9300C18—C191.414 (4)
C5—C61.526 (3)C18—H180.9300
O1—Zn1—O1i180.0O3—C6—C5114.1 (2)
O1—Zn1—N1i99.32 (7)N3—C7—C8120.4 (2)
O1i—Zn1—N1i80.68 (7)N3—C7—C12119.5 (2)
O1—Zn1—N180.68 (7)C8—C7—C12120.1 (2)
O1i—Zn1—N199.32 (7)C9—C8—C7119.3 (2)
N1i—Zn1—N1180.0C9—C8—H8120.4
O1—Zn1—O4ii86.88 (7)C7—C8—H8120.4
O1i—Zn1—O4ii93.12 (7)C8—C9—C10121.2 (2)
N1i—Zn1—O4ii89.71 (7)C8—C9—H9119.4
N1—Zn1—O4ii90.29 (7)C10—C9—H9119.4
O1—Zn1—O4iii93.12 (7)C11—C10—C9120.8 (2)
O1i—Zn1—O4iii86.88 (7)C11—C10—H10119.6
N1i—Zn1—O4iii90.29 (7)C9—C10—H10119.6
N1—Zn1—O4iii89.71 (7)C10—C11—C12120.1 (2)
O4ii—Zn1—O4iii180.000 (1)C10—C11—H11120.0
C3—N1—C2118.8 (2)C12—C11—H11120.0
C3—N1—Zn1129.49 (17)C13—C12—C11122.9 (2)
C2—N1—Zn1111.71 (16)C13—C12—C7118.5 (2)
C4—N2—C5116.2 (2)C11—C12—C7118.6 (2)
C7—N3—C19122.7 (2)C12—C13—C14121.2 (2)
C7—N3—H3N115.6 (19)C12—C13—H13119.4
C19—N3—H3N121.6 (19)C14—C13—H13119.4
C1—O1—Zn1115.63 (15)C13—C14—C19119.0 (2)
C6—O4—Zn1iv145.70 (16)C13—C14—C15122.8 (2)
O2—C1—O1126.6 (2)C19—C14—C15118.2 (2)
O2—C1—C2117.0 (2)C16—C15—C14120.8 (2)
O1—C1—C2116.4 (2)C16—C15—H15119.6
N1—C2—C5119.9 (2)C14—C15—H15119.6
N1—C2—C1115.5 (2)C15—C16—C17119.6 (2)
C5—C2—C1124.7 (2)C15—C16—H16120.2
N1—C3—C4120.1 (2)C17—C16—H16120.2
N1—C3—H3119.9C18—C17—C16122.1 (2)
C4—C3—H3119.9C18—C17—H17118.9
N2—C4—C3123.1 (2)C16—C17—H17118.9
N2—C4—H4118.5C17—C18—C19118.7 (2)
C3—C4—H4118.5C17—C18—H18120.6
N2—C5—C2121.9 (2)C19—C18—H18120.6
N2—C5—C6115.7 (2)N3—C19—C18120.4 (2)
C2—C5—C6122.3 (2)N3—C19—C14119.1 (2)
O4—C6—O3126.0 (2)C18—C19—C14120.5 (2)
O4—C6—C5119.9 (2)
O1—Zn1—N1—C3179.3 (2)N2—C5—C6—O483.9 (3)
O1i—Zn1—N1—C30.7 (2)C2—C5—C6—O498.6 (3)
O4ii—Zn1—N1—C392.5 (2)N2—C5—C6—O393.2 (3)
O4iii—Zn1—N1—C387.5 (2)C2—C5—C6—O384.3 (3)
O1—Zn1—N1—C21.26 (16)C19—N3—C7—C8177.2 (2)
O1i—Zn1—N1—C2178.74 (16)C19—N3—C7—C122.4 (4)
O4ii—Zn1—N1—C288.05 (16)N3—C7—C8—C9179.3 (2)
O4iii—Zn1—N1—C291.95 (16)C12—C7—C8—C90.4 (4)
N1i—Zn1—O1—C1177.15 (17)C7—C8—C9—C100.8 (4)
N1—Zn1—O1—C12.85 (17)C8—C9—C10—C110.8 (4)
O4ii—Zn1—O1—C193.66 (17)C9—C10—C11—C120.2 (4)
O4iii—Zn1—O1—C186.34 (17)C10—C11—C12—C13179.4 (2)
Zn1—O1—C1—O2175.2 (2)C10—C11—C12—C70.2 (4)
Zn1—O1—C1—C23.8 (3)N3—C7—C12—C130.1 (3)
C3—N1—C2—C50.7 (3)C8—C7—C12—C13179.5 (2)
Zn1—N1—C2—C5179.80 (17)N3—C7—C12—C11179.8 (2)
C3—N1—C2—C1179.3 (2)C8—C7—C12—C110.2 (3)
Zn1—N1—C2—C10.2 (2)C11—C12—C13—C14178.3 (2)
O2—C1—C2—N1176.4 (2)C7—C12—C13—C141.4 (4)
O1—C1—C2—N12.7 (3)C12—C13—C14—C190.7 (4)
O2—C1—C2—C53.6 (4)C12—C13—C14—C15178.8 (2)
O1—C1—C2—C5177.4 (2)C13—C14—C15—C16178.9 (2)
C2—N1—C3—C40.7 (4)C19—C14—C15—C160.6 (4)
Zn1—N1—C3—C4179.85 (18)C14—C15—C16—C170.7 (4)
C5—N2—C4—C30.7 (4)C15—C16—C17—C181.6 (4)
N1—C3—C4—N20.0 (4)C16—C17—C18—C191.2 (4)
C4—N2—C5—C20.7 (4)C7—N3—C19—C18176.9 (2)
C4—N2—C5—C6178.2 (2)C7—N3—C19—C143.1 (4)
N1—C2—C5—N20.1 (4)C17—C18—C19—N3179.8 (2)
C1—C2—C5—N2179.9 (2)C17—C18—C19—C140.2 (4)
N1—C2—C5—C6177.4 (2)C13—C14—C19—N31.6 (3)
C1—C2—C5—C62.6 (4)C15—C14—C19—N3178.9 (2)
Zn1iv—O4—C6—O3171.95 (18)C13—C14—C19—C18178.4 (2)
Zn1iv—O4—C6—C511.3 (4)C15—C14—C19—C181.1 (3)
Symmetry codes: (i) x+2, y+2, z+1; (ii) x, y+1, z; (iii) x+2, y+1, z+1; (iv) x, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O30.86 (2)1.78 (2)2.634 (3)172 (3)
C13—H13···O2v0.932.383.211 (4)149
C16—H16···O3vi0.932.493.377 (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]
Mr758.00
Crystal system, space groupMonoclinic, P21/c
Temperature (K)120
a, b, c (Å)13.2256 (12), 6.8141 (6), 17.9889 (16)
β (°) 111.013 (2)
V3)1513.4 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.88
Crystal size (mm)0.27 × 0.15 × 0.13
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick 1998)
Tmin, Tmax0.845, 0.891
No. of measured, independent and
observed [I > 2σ(I)] reflections
15968, 2720, 2292
Rint0.032
(sin θ/λ)max1)0.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.115, 1.14
No. of reflections2720
No. of parameters244
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.76, 0.47

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

Selected bond lengths (Å) top
Zn1—O12.0326 (17)Zn1—O4i2.2435 (17)
Zn1—N12.093 (2)
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O30.86 (2)1.78 (2)2.634 (3)172 (3)
C13—H13···O2ii0.932.383.211 (4)149
C16—H16···O3iii0.932.493.377 (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

First citationAghabozorg, H., Attar Gharamaleki, J., Parvizi, M. & Derikvand, Z. (2010b). Acta Cryst. E66, m83–m84.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationAghabozorg, H., Eshtiagh-Hosseini, H., Salimi, A. R. & Mirzaei, M. (2010a). J. Iran. Chem. Soc. 7, 289–300.  CrossRef CAS Google Scholar
First citationBruker (1998). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (1998). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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