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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 8| August 2012| Page m1072
https://doi.org/10.1107/S1600536812031443

Bis[2,6-bis­­(1-methyl-1H-benzimidazol-2-yl-κN3)pyridine-κN]zinc dipicrate methanol disolvate

Xuyang Fan,a Jingkun Yuan,a Ying Bai,a Jin Konga and Huilu Wua*

aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
*Correspondence e-mail: wuhuilu@163.com

(Received 11 June 2012; accepted 10 July 2012; online 14 July 2012)

In the title compound, [Zn(C21H17N5)2](C6H2N3O7)2·2CH3OH, the ZnII atom is coordinated by six N atoms from two tridentate 2,6-bis­(1-methyl-1H-benzimidazol-2-yl)pyridine ligands in a distorted octa­hedral environment. In the crystal, the picrate anions and methanol solvent mol­ecules are connected by O—H⋯O hydrogen bonds. Weak inter­molecular C—H⋯O hydrogen bonds are also observed.

Related literature

For the applications of benzimidazole derivatives, see: Horton et al. (2003[Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893-930.]); Wang et al. (1994[Wang, S. X., Yu, S. Y. & Luo, Q. H. (1994). Transition Met. Chem. 19, 205-208.]); Cowan (1998[Cowan, J. A. (1998). Chem. Rev. 98, 1067-1088.]); Liu et al. (2004[Liu, C. L., Wang, M., Zhang, T. L. & Sun, H. Z. (2004). Coord. Chem. Rev. 248, 147-168.], 2011[Liu, H. Y., Wu, H., Yang, J., Liu, Y. Y., Liu, B., Liu, Y. Y. & Ma, J. F. (2011). Cryst. Growth Des. 11, 2920-2927.]); Wright (1951[Wright, J. B. (1951). Chem. Rev. 48, 397-541.]). For a related crystal structure, see: Huang et al. (2010[Huang, X., Kou, F., Qi, B., Meng, X. & Wu, H. (2010). Acta Cryst. E66, m967.]).

[Scheme 1]

Experimental

Crystal data

  • [Zn(C21H17N5)2](C6H2N3O7)2·2CH4O

  • Mr = 1264.46

  • Triclinic, [P \overline 1]

  • a = 13.2007 (3) Å

  • b = 13.8024 (3) Å

  • c = 16.2009 (3) Å

  • α = 80.811 (1)°

  • β = 71.012 (1)°

  • γ = 88.538 (1)°

  • V = 2754.28 (10) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.54 mm−1

  • T = 153 K

  • 0.38 × 0.36 × 0.30 mm
Data collection

  • Bruker APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.816, Tmax = 0.852

  • 22669 measured reflections

  • 10148 independent reflections

  • 9024 reflections with I > 2σ(I)

  • Rint = 0.017
Refinement

  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.111

  • S = 1.07

  • 10148 reflections

  • 811 parameters

  • H-atom parameters constrained

  • Δρmax = 0.78 e Å−3

  • Δρmin = −0.51 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O15—H15⋯O1i 0.84 1.94 2.756 (4) 165
C31—H31A⋯O2i 0.95 2.53 3.204 (3) 128
C42—H42A⋯O1i 0.98 2.32 3.106 (3) 137
C55—H55C⋯O9ii 0.98 2.56 3.415 (7) 146
C11—H11A⋯O11iii 0.95 2.39 3.207 (3) 144
C10—H10A⋯O3iv 0.95 2.37 3.233 (3) 152
C4—H4A⋯O4v 0.95 2.50 3.333 (3) 146
C37—H37A⋯O11vi 0.95 2.49 3.314 (3) 146
C10—H10A⋯O10vii 0.95 2.57 3.133 (4) 118
C20—H20B⋯O14vii 0.98 2.42 2.949 (3) 113
Symmetry codes: (i) x, y, z+1; (ii) x, y+1, z; (iii) x+1, y+1, z-1; (iv) x+1, y, z; (v) -x, -y+1, -z+1; (vi) -x+1, -y, -z+2; (vii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812031443/lh5492sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812031443/lh5492Isup2.hkl

checkCIF report


Comment top

Benzimidazole and its derivatives have attracted considerable interests in recent years for their versatile properties in chemistry and pharmacology (Wang et al. 1994; Horton et al. 2003). As a part of the chemical structure of vitamin B12 (Wright 1951), benzimidazole scaffolds have shown wide application in medicine, fungicide, biochemical reagents and many other fields (Cowan 1998; Liu et al. 2004). Moreover, as a typical heterocyclic ligand, the large benzimidazole rings not only can provide potential supermolecule recognition sites for π···π stacking interactions, but also act as hydrogen bond acceptors and donors to assemble multiple coordination geometries (Liu et al. 2011). As part of our reasearch in this area we have already determined the crystal structure of bis[2,6-bis(1H-benzimidazol-2-yl)pyridine]nickel(II) dipicrate dimethylformamide disolvate (Huang et al., 2010) and the crystal structure of the title compound is presented herein.

The asymmetric unit of the title complex consists of a [ZnII(bmbp)2] cation (bmbp = 2,6-bis(N-methylbenzimidazol-2-yl)pyridine) (Fig. 1), two picrate anions and two methanol solvent molecules. The ZnII ion is coordinated by six N atoms from two two tridentate V-shaped ligands (bmbp) ligands in a distorted octacahedral enviroment. In the crystal, the picrate anions and solvent methanol molecules are connected by O—H···O hydrogen bonds. Weak intermolecular C—H···O hydrogen bonds are also observed (Fig. 2).

Related literature top

For the applications of benzimidazole derivatives, see: Horton et al. (2003); Wang et al. (1994); Cowan (1998); Liu et al. (2004, 2011); Wright (1951). For a related crystal structure, see: Huang et al. (2010).

Experimental top

To a stirred solution of 2,6-bis(N-ethylbenzimidazol-2-yl)pyridine (0.1697 g, 0.50 mmol) in hot MeOH (10 ml) was added Zn(picrate)2 (0.1304 g, 0.25 mmol) solution dissolved in MeOH (5 ml). A yellow crystalline product formed rapidly immediately. The sediment was filtered off, washed with MeOH and absolute Et2O, and dried in vacuo. The crude product was dissolved in mixed MeOH-DMF solution to form a pale yellow solution into which Et2O was allowed to diffuse at room temperature. Yellow crystals of it suitable for X-ray measurement were obtained after two weeks. (found: C, 53.45; H, 3.84; N, 17.55. Calcd. for C56 H46 N16 O16 Zn: C, 53.27; H, 3.67; N, 17.75)

Refinement top

All H atoms were found in difference electron maps and were subsequently included in a riding-model approximation with C—H distances ranging from 0.95 to 0.98 Å and Uiso(H) = 1.2 Ueq(C),Uiso(H) = 1.5Ueq(Cmethyl).

Structure description top

Benzimidazole and its derivatives have attracted considerable interests in recent years for their versatile properties in chemistry and pharmacology (Wang et al. 1994; Horton et al. 2003). As a part of the chemical structure of vitamin B12 (Wright 1951), benzimidazole scaffolds have shown wide application in medicine, fungicide, biochemical reagents and many other fields (Cowan 1998; Liu et al. 2004). Moreover, as a typical heterocyclic ligand, the large benzimidazole rings not only can provide potential supermolecule recognition sites for π···π stacking interactions, but also act as hydrogen bond acceptors and donors to assemble multiple coordination geometries (Liu et al. 2011). As part of our reasearch in this area we have already determined the crystal structure of bis[2,6-bis(1H-benzimidazol-2-yl)pyridine]nickel(II) dipicrate dimethylformamide disolvate (Huang et al., 2010) and the crystal structure of the title compound is presented herein.

The asymmetric unit of the title complex consists of a [ZnII(bmbp)2] cation (bmbp = 2,6-bis(N-methylbenzimidazol-2-yl)pyridine) (Fig. 1), two picrate anions and two methanol solvent molecules. The ZnII ion is coordinated by six N atoms from two two tridentate V-shaped ligands (bmbp) ligands in a distorted octacahedral enviroment. In the crystal, the picrate anions and solvent methanol molecules are connected by O—H···O hydrogen bonds. Weak intermolecular C—H···O hydrogen bonds are also observed (Fig. 2).

For the applications of benzimidazole derivatives, see: Horton et al. (2003); Wang et al. (1994); Cowan (1998); Liu et al. (2004, 2011); Wright (1951). For a related crystal structure, see: Huang et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the [ZnII(bmbp)2] cation. Displacement ellipsoids are drawn at the 30% probability level. H atoms and methanol solvate molecules have been omitted for clarity.
[Figure 2] Fig. 2. The crystal packing of the title compound. Intermolecular hydrogen bonds are shown as dashed lines.
Bis[2,6-bis(1-methyl-1H-benzimidazol-2-yl-κN3)pyridine- κN]zinc dipicrate methanol disolvate top
Crystal data top
[Zn(C21H17N5)2](C6H2N3O7)2·2CH4OZ = 2
Mr = 1264.46F(000) = 1304
Triclinic, P1Dx = 1.525 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 13.2007 (3) ÅCell parameters from 10153 reflections
b = 13.8024 (3) Åθ = 3.1–25.5°
c = 16.2009 (3) ŵ = 0.54 mm−1
α = 80.811 (1)°T = 153 K
β = 71.012 (1)°Block, yellow
γ = 88.538 (1)°0.38 × 0.36 × 0.30 mm
V = 2754.28 (10) Å3
Data collection top
Bruker APEXII area-detector
diffractometer		10148 independent reflections
Radiation source: fine-focus sealed tube9024 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
ω scansθmax = 25.5°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −15→15
Tmin = 0.816, Tmax = 0.852k = −16→16
22669 measured reflectionsl = −19→19
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.0558P)2 + 2.8031P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
10148 reflectionsΔρmax = 0.78 e Å−3
811 parametersΔρmin = −0.51 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0020 (4)
Crystal data top
[Zn(C21H17N5)2](C6H2N3O7)2·2CH4Oγ = 88.538 (1)°
Mr = 1264.46V = 2754.28 (10) Å3
Triclinic, P1Z = 2
a = 13.2007 (3) ÅMo Kα radiation
b = 13.8024 (3) ŵ = 0.54 mm−1
c = 16.2009 (3) ÅT = 153 K
α = 80.811 (1)°0.38 × 0.36 × 0.30 mm
β = 71.012 (1)°
Data collection top
Bruker APEXII area-detector
diffractometer		10148 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		9024 reflections with I > 2σ(I)
Tmin = 0.816, Tmax = 0.852Rint = 0.017
22669 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.111H-atom parameters constrained
S = 1.07Δρmax = 0.78 e Å−3
10148 reflectionsΔρmin = −0.51 e Å−3
811 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 > 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
xyzUiso*/Ueq
Zn0.699284 (19)0.754092 (17)0.578747 (15)0.01513 (9)
O10.28834 (17)0.53363 (17)−0.01056 (13)0.0503 (6)
O20.26536 (18)0.71973 (17)0.03078 (17)0.0626 (7)
O30.09610 (17)0.74158 (14)0.08634 (14)0.0466 (5)
O4−0.06207 (15)0.51349 (16)0.35968 (13)0.0431 (5)
O5−0.0202 (2)0.36062 (17)0.36496 (15)0.0604 (7)
O60.2169 (3)0.25914 (18)0.08881 (19)0.1090 (15)
O70.3604 (2)0.3520 (2)0.03785 (19)0.0708 (8)
O80.31607 (15)0.12803 (13)0.81934 (11)0.0343 (4)
O90.1328 (3)−0.0774 (3)0.8911 (2)0.0944 (11)
O100.0861 (3)0.0692 (2)0.8926 (3)0.1292 (18)
O110.19845 (16)−0.12180 (14)1.19446 (12)0.0403 (5)
O120.33643 (18)−0.04076 (16)1.19439 (13)0.0471 (5)
O130.53377 (15)0.18178 (15)0.94195 (13)0.0418 (5)
O140.4566 (3)0.2465 (2)0.85048 (19)0.0943 (12)
O150.2472 (3)0.6163 (3)0.8375 (2)0.1042 (12)
H150.26320.60130.88400.125*
O160.8403 (3)0.5680 (3)0.1703 (2)0.0917 (10)
H160.81690.51340.16650.110*
N10.61233 (14)0.67598 (13)0.51819 (11)0.0174 (4)
N20.58800 (15)0.65098 (13)0.39274 (11)0.0176 (4)
N30.84613 (14)0.82283 (13)0.57262 (11)0.0179 (4)
N41.01794 (14)0.86493 (13)0.49867 (12)0.0192 (4)
N50.80558 (14)0.75208 (12)0.44653 (11)0.0161 (4)
N60.63124 (14)0.89742 (13)0.54757 (11)0.0174 (4)
N70.58053 (15)1.03783 (13)0.59946 (12)0.0193 (4)
N80.69979 (14)0.62875 (13)0.67234 (11)0.0168 (4)
N90.60273 (15)0.53039 (14)0.79475 (12)0.0204 (4)
N100.59056 (14)0.78586 (13)0.70167 (12)0.0174 (4)
N110.17438 (18)0.68927 (17)0.07385 (14)0.0344 (5)
N12−0.01124 (18)0.44612 (18)0.32607 (15)0.0368 (5)
N130.2646 (3)0.33716 (19)0.07852 (16)0.0504 (7)
N140.1388 (2)0.0044 (2)0.90879 (16)0.0447 (6)
N150.27282 (17)−0.06106 (16)1.15817 (14)0.0315 (5)
N160.46173 (18)0.18250 (17)0.90974 (14)0.0367 (5)
C10.50998 (17)0.63813 (15)0.53891 (14)0.0170 (4)
C20.42797 (18)0.61677 (15)0.62057 (14)0.0203 (5)
H2A0.43920.62470.67420.024*
C30.33074 (19)0.58396 (16)0.61995 (15)0.0235 (5)
H3A0.27350.56980.67420.028*
C40.31384 (19)0.57089 (17)0.54111 (16)0.0257 (5)
H4A0.24530.54870.54350.031*
C50.39438 (19)0.58948 (16)0.46001 (15)0.0230 (5)
H5A0.38330.57980.40680.028*
C60.49255 (18)0.62310 (15)0.46096 (14)0.0185 (4)
C70.65650 (17)0.68154 (15)0.43119 (14)0.0169 (4)
C80.76679 (17)0.72233 (15)0.38747 (14)0.0176 (4)
C90.82556 (19)0.73526 (18)0.29843 (15)0.0252 (5)
H9A0.79840.71290.25700.030*
C100.92543 (19)0.78191 (18)0.27147 (15)0.0267 (5)
H10A0.96710.79230.21060.032*
C110.96532 (18)0.81369 (17)0.33225 (15)0.0227 (5)
H11A1.03360.84580.31400.027*
C120.90227 (17)0.79702 (15)0.42037 (14)0.0180 (4)
C130.92473 (17)0.82849 (15)0.49604 (14)0.0171 (4)
C140.99804 (18)0.88374 (16)0.58402 (14)0.0195 (4)
C151.06430 (19)0.92029 (17)0.62419 (16)0.0259 (5)
H15A1.13720.93860.59260.031*
C161.0183 (2)0.92849 (18)0.71214 (16)0.0279 (5)
H16A1.06090.95270.74210.034*
C170.9104 (2)0.90203 (18)0.75876 (16)0.0270 (5)
H17A0.88200.90840.81950.032*
C180.84469 (19)0.86709 (17)0.71870 (15)0.0239 (5)
H18A0.77140.85040.75020.029*
C190.89030 (17)0.85717 (16)0.62963 (14)0.0193 (4)
C200.6048 (2)0.64939 (18)0.29902 (14)0.0264 (5)
H20B0.62260.71600.26580.040*
H20A0.53920.62510.29240.040*
H20C0.66370.60600.27620.040*
C211.12344 (18)0.8786 (2)0.43008 (16)0.0292 (5)
H21A1.11910.92720.38020.044*
H21B1.14620.81600.40960.044*
H21C1.17550.90170.45450.044*
C220.65157 (16)0.97291 (15)0.47651 (14)0.0181 (4)
C230.69229 (17)0.97117 (17)0.38526 (14)0.0209 (5)
H23A0.71240.91150.36280.025*
C240.70186 (18)1.05972 (17)0.32951 (15)0.0243 (5)
H24A0.72771.06050.26740.029*
C250.6746 (2)1.14826 (18)0.36181 (16)0.0274 (5)
H25A0.68421.20780.32120.033*
C260.63384 (19)1.15113 (17)0.45178 (16)0.0253 (5)
H26A0.61541.21110.47400.030*
C270.62140 (17)1.06121 (16)0.50801 (14)0.0195 (4)
C280.58735 (17)0.93899 (16)0.61897 (14)0.0177 (4)
C290.55061 (17)0.87549 (16)0.70641 (14)0.0187 (4)
C300.47846 (19)0.89771 (17)0.78492 (15)0.0236 (5)
H30A0.45050.96160.78850.028*
C310.4488 (2)0.82381 (18)0.85764 (16)0.0279 (5)
H31A0.39950.83710.91190.033*
C320.49012 (19)0.73043 (18)0.85238 (15)0.0254 (5)
H32A0.46950.67950.90210.031*
C330.56265 (17)0.71397 (16)0.77206 (14)0.0190 (4)
C340.62009 (17)0.62350 (16)0.74933 (14)0.0180 (4)
C350.67656 (18)0.47211 (16)0.74403 (14)0.0196 (4)
C360.6950 (2)0.37193 (17)0.75803 (15)0.0249 (5)
H36A0.65400.32960.80990.030*
C370.7761 (2)0.33797 (17)0.69232 (16)0.0289 (5)
H37A0.79160.27010.69930.035*
C380.8371 (2)0.40011 (18)0.61503 (16)0.0273 (5)
H38A0.89240.37320.57150.033*
C390.81817 (18)0.49872 (17)0.60134 (14)0.0212 (5)
H39A0.85890.54050.54910.025*
C400.73637 (17)0.53509 (15)0.66761 (14)0.0175 (4)
C410.5416 (2)1.10995 (17)0.65917 (16)0.0267 (5)
H41A0.56831.09450.70950.040*
H41B0.46311.10770.68070.040*
H41C0.56751.17580.62730.040*
C420.5218 (2)0.49229 (19)0.87971 (16)0.0356 (6)
H42A0.45250.52110.88180.053*
H42B0.54330.50960.92810.053*
H42C0.51540.42070.88600.053*
C430.2241 (2)0.5146 (2)0.06625 (17)0.0326 (6)
C440.15790 (19)0.58601 (18)0.11362 (16)0.0276 (5)
C450.08051 (19)0.56413 (18)0.19506 (16)0.0264 (5)
H45A0.03810.61450.22180.032*
C460.06500 (19)0.46772 (19)0.23775 (16)0.0285 (5)
C470.1249 (2)0.3934 (2)0.19830 (17)0.0341 (6)
H47A0.11300.32710.22720.041*
C480.2016 (2)0.4171 (2)0.11696 (17)0.0356 (6)
C490.30545 (19)0.09229 (17)0.89718 (14)0.0229 (5)
C500.2194 (2)0.02170 (18)0.94949 (15)0.0264 (5)
C510.2092 (2)−0.02996 (17)1.03094 (16)0.0275 (5)
H51A0.1530−0.07771.05960.033*
C520.28341 (19)−0.01071 (17)1.07077 (15)0.0252 (5)
C530.36580 (19)0.05843 (18)1.02961 (15)0.0258 (5)
H53A0.41510.07121.05850.031*
C540.37602 (19)0.10873 (17)0.94652 (15)0.0245 (5)
C550.1576 (6)0.6855 (4)0.8528 (4)0.121 (2)
H55A0.09670.65590.90300.145*
H55B0.13590.69970.79980.145*
H55C0.18090.74660.86560.145*
C560.8505 (5)0.6345 (4)0.0916 (3)0.0966 (17)
H56A0.78050.64150.08270.116*
H56B0.90160.60950.04120.116*
H56C0.87640.69860.09640.116*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.01501 (14)0.01619 (14)0.01242 (13)−0.00262 (9)−0.00208 (9)−0.00181 (9)
O10.0440 (12)0.0594 (14)0.0294 (10)0.0121 (10)0.0103 (9)−0.0040 (10)
O20.0407 (13)0.0534 (14)0.0658 (15)−0.0173 (11)0.0128 (11)0.0094 (12)
O30.0482 (13)0.0319 (10)0.0438 (12)0.0051 (9)0.0047 (9)−0.0029 (9)
O40.0291 (10)0.0536 (13)0.0337 (10)−0.0006 (9)0.0064 (8)−0.0049 (9)
O50.0675 (16)0.0447 (13)0.0449 (13)−0.0072 (11)0.0056 (11)0.0132 (11)
O60.157 (3)0.0329 (14)0.0711 (19)0.0022 (17)0.051 (2)−0.0056 (13)
O70.0545 (16)0.0847 (19)0.0792 (18)0.0369 (14)−0.0203 (14)−0.0387 (15)
O80.0442 (11)0.0370 (10)0.0197 (9)−0.0088 (8)−0.0109 (8)0.0039 (8)
O90.117 (3)0.100 (2)0.091 (2)−0.023 (2)−0.055 (2)−0.0398 (19)
O100.126 (3)0.077 (2)0.229 (5)−0.032 (2)−0.148 (3)0.044 (3)
O110.0401 (11)0.0403 (11)0.0287 (9)−0.0055 (9)−0.0044 (8)0.0151 (8)
O120.0518 (13)0.0590 (13)0.0316 (10)−0.0074 (10)−0.0238 (10)0.0129 (9)
O130.0308 (10)0.0539 (12)0.0392 (11)−0.0127 (9)−0.0146 (9)0.0057 (9)
O140.109 (2)0.099 (2)0.0811 (19)−0.0802 (19)−0.0744 (18)0.0726 (17)
O150.139 (3)0.128 (3)0.0483 (17)0.005 (3)−0.0323 (19)−0.0185 (19)
O160.095 (2)0.107 (3)0.081 (2)0.011 (2)−0.0284 (18)−0.040 (2)
N10.0185 (9)0.0163 (9)0.0168 (9)−0.0022 (7)−0.0049 (7)−0.0025 (7)
N20.0213 (9)0.0164 (9)0.0161 (9)−0.0020 (7)−0.0073 (7)−0.0027 (7)
N30.0178 (9)0.0184 (9)0.0161 (9)−0.0032 (7)−0.0035 (7)−0.0019 (7)
N40.0143 (9)0.0208 (9)0.0208 (9)−0.0024 (7)−0.0029 (7)−0.0042 (7)
N50.0178 (9)0.0158 (8)0.0134 (8)−0.0008 (7)−0.0035 (7)−0.0016 (7)
N60.0172 (9)0.0176 (9)0.0156 (9)−0.0012 (7)−0.0034 (7)−0.0010 (7)
N70.0200 (9)0.0180 (9)0.0201 (9)0.0025 (7)−0.0063 (7)−0.0043 (7)
N80.0165 (9)0.0191 (9)0.0134 (8)−0.0018 (7)−0.0037 (7)−0.0009 (7)
N90.0215 (10)0.0209 (9)0.0148 (9)−0.0030 (7)−0.0020 (7)0.0011 (7)
N100.0146 (9)0.0197 (9)0.0177 (9)−0.0015 (7)−0.0046 (7)−0.0034 (7)
N110.0337 (13)0.0350 (12)0.0267 (11)−0.0066 (10)0.0010 (9)−0.0041 (9)
N120.0263 (11)0.0442 (14)0.0326 (12)−0.0065 (10)−0.0027 (9)0.0013 (11)
N130.075 (2)0.0405 (15)0.0276 (12)0.0190 (14)−0.0077 (13)−0.0047 (11)
N140.0501 (15)0.0502 (15)0.0335 (12)−0.0234 (13)−0.0204 (11)0.0123 (12)
N150.0323 (12)0.0335 (12)0.0225 (10)0.0014 (9)−0.0055 (9)0.0064 (9)
N160.0355 (13)0.0432 (13)0.0281 (11)−0.0151 (10)−0.0117 (10)0.0093 (10)
C10.0192 (11)0.0114 (9)0.0205 (10)0.0000 (8)−0.0072 (9)−0.0010 (8)
C20.0236 (11)0.0164 (10)0.0195 (11)−0.0010 (8)−0.0061 (9)−0.0002 (9)
C30.0220 (12)0.0216 (11)0.0234 (11)−0.0027 (9)−0.0043 (9)0.0005 (9)
C40.0199 (12)0.0246 (12)0.0318 (13)−0.0058 (9)−0.0084 (10)−0.0012 (10)
C50.0255 (12)0.0206 (11)0.0265 (12)−0.0023 (9)−0.0132 (10)−0.0037 (9)
C60.0216 (11)0.0143 (10)0.0194 (11)−0.0023 (8)−0.0073 (9)−0.0003 (8)
C70.0197 (11)0.0141 (10)0.0172 (10)−0.0009 (8)−0.0062 (8)−0.0031 (8)
C80.0201 (11)0.0150 (10)0.0168 (10)−0.0008 (8)−0.0046 (8)−0.0024 (8)
C90.0254 (12)0.0305 (12)0.0197 (11)−0.0014 (10)−0.0053 (9)−0.0079 (10)
C100.0250 (12)0.0346 (13)0.0139 (10)−0.0007 (10)0.0024 (9)−0.0034 (10)
C110.0189 (11)0.0250 (11)0.0198 (11)−0.0025 (9)−0.0011 (9)−0.0018 (9)
C120.0163 (10)0.0165 (10)0.0204 (11)0.0005 (8)−0.0048 (8)−0.0032 (8)
C130.0162 (10)0.0155 (10)0.0177 (10)−0.0024 (8)−0.0040 (8)−0.0003 (8)
C140.0193 (11)0.0175 (10)0.0215 (11)−0.0003 (8)−0.0061 (9)−0.0036 (9)
C150.0201 (12)0.0277 (12)0.0310 (13)−0.0036 (9)−0.0091 (10)−0.0057 (10)
C160.0286 (13)0.0313 (13)0.0296 (13)−0.0023 (10)−0.0151 (10)−0.0091 (10)
C170.0314 (13)0.0300 (13)0.0208 (11)−0.0006 (10)−0.0084 (10)−0.0077 (10)
C180.0228 (12)0.0262 (12)0.0209 (11)−0.0028 (9)−0.0043 (9)−0.0042 (9)
C190.0192 (11)0.0173 (10)0.0223 (11)−0.0014 (8)−0.0079 (9)−0.0025 (9)
C200.0349 (13)0.0292 (12)0.0163 (11)−0.0097 (10)−0.0113 (10)0.0006 (9)
C210.0169 (11)0.0396 (14)0.0276 (12)−0.0076 (10)0.0010 (9)−0.0113 (11)
C220.0131 (10)0.0177 (10)0.0237 (11)−0.0012 (8)−0.0072 (8)−0.0016 (9)
C230.0181 (11)0.0242 (11)0.0199 (11)0.0000 (9)−0.0055 (9)−0.0040 (9)
C240.0226 (12)0.0302 (12)0.0197 (11)0.0005 (9)−0.0080 (9)0.0002 (10)
C250.0280 (13)0.0240 (12)0.0286 (12)0.0016 (10)−0.0112 (10)0.0041 (10)
C260.0256 (12)0.0205 (11)0.0296 (12)0.0058 (9)−0.0100 (10)−0.0021 (10)
C270.0156 (10)0.0220 (11)0.0208 (11)0.0008 (8)−0.0062 (8)−0.0030 (9)
C280.0151 (10)0.0185 (10)0.0184 (10)−0.0001 (8)−0.0039 (8)−0.0025 (9)
C290.0170 (10)0.0195 (11)0.0208 (11)−0.0010 (8)−0.0071 (8)−0.0044 (9)
C300.0236 (12)0.0246 (12)0.0215 (11)0.0033 (9)−0.0046 (9)−0.0070 (9)
C310.0252 (12)0.0345 (13)0.0207 (11)0.0031 (10)−0.0019 (9)−0.0071 (10)
C320.0266 (12)0.0275 (12)0.0177 (11)0.0002 (10)−0.0026 (9)−0.0005 (9)
C330.0186 (11)0.0222 (11)0.0151 (10)−0.0023 (9)−0.0052 (8)−0.0002 (9)
C340.0185 (11)0.0197 (11)0.0155 (10)−0.0016 (8)−0.0058 (8)−0.0007 (8)
C350.0211 (11)0.0213 (11)0.0159 (10)−0.0026 (9)−0.0059 (8)−0.0013 (9)
C360.0336 (13)0.0199 (11)0.0197 (11)−0.0033 (9)−0.0088 (10)0.0018 (9)
C370.0393 (14)0.0194 (11)0.0281 (12)0.0022 (10)−0.0116 (11)−0.0028 (10)
C380.0300 (13)0.0258 (12)0.0251 (12)0.0062 (10)−0.0062 (10)−0.0073 (10)
C390.0211 (11)0.0240 (11)0.0165 (10)−0.0025 (9)−0.0041 (9)−0.0015 (9)
C400.0184 (11)0.0185 (10)0.0162 (10)−0.0022 (8)−0.0070 (8)−0.0018 (8)
C410.0337 (13)0.0208 (11)0.0269 (12)0.0074 (10)−0.0097 (10)−0.0091 (10)
C420.0394 (15)0.0295 (13)0.0200 (12)−0.0055 (11)0.0112 (11)0.0047 (10)
C430.0281 (13)0.0408 (15)0.0262 (13)0.0052 (11)−0.0049 (10)−0.0064 (11)
C440.0224 (12)0.0309 (13)0.0259 (12)−0.0024 (10)−0.0031 (10)−0.0039 (10)
C450.0192 (11)0.0319 (13)0.0261 (12)−0.0005 (10)−0.0041 (9)−0.0058 (10)
C460.0233 (12)0.0359 (14)0.0226 (12)−0.0042 (10)−0.0040 (10)−0.0004 (10)
C470.0419 (16)0.0318 (14)0.0295 (13)0.0014 (11)−0.0141 (12)−0.0024 (11)
C480.0416 (16)0.0386 (15)0.0281 (13)0.0126 (12)−0.0118 (12)−0.0103 (12)
C490.0267 (12)0.0218 (11)0.0168 (11)0.0013 (9)−0.0033 (9)−0.0011 (9)
C500.0296 (13)0.0258 (12)0.0228 (12)−0.0032 (10)−0.0083 (10)−0.0010 (10)
C510.0287 (13)0.0239 (12)0.0241 (12)−0.0036 (10)−0.0039 (10)0.0030 (10)
C520.0279 (12)0.0244 (12)0.0177 (11)0.0039 (10)−0.0041 (9)0.0051 (9)
C530.0243 (12)0.0302 (12)0.0226 (11)0.0028 (10)−0.0092 (9)−0.0002 (10)
C540.0247 (12)0.0238 (12)0.0208 (11)−0.0021 (9)−0.0043 (9)0.0026 (9)
C550.165 (6)0.100 (4)0.074 (3)0.034 (4)−0.017 (4)0.000 (3)
C560.119 (4)0.120 (4)0.049 (2)−0.042 (3)−0.019 (2)−0.020 (3)
Geometric parameters (Å, º) top
Zn—N82.1119 (17)C14—C151.393 (3)
Zn—N12.1392 (18)C14—C191.400 (3)
Zn—N102.1459 (18)C15—C161.377 (3)
Zn—N32.1462 (18)C15—H15A0.9500
Zn—N52.1493 (17)C16—C171.405 (3)
Zn—N62.2048 (18)C16—H16A0.9500
O1—C431.248 (3)C17—C181.376 (3)
O2—N111.222 (3)C17—H17A0.9500
O3—N111.226 (3)C18—C191.399 (3)
O4—N121.226 (3)C18—H18A0.9500
O5—N121.235 (3)C20—H20B0.9800
O6—N131.221 (4)C20—H20A0.9800
O7—N131.226 (4)C20—H20C0.9800
O8—C491.242 (3)C21—H21A0.9800
O9—N141.219 (4)C21—H21B0.9800
O10—N141.168 (4)C21—H21C0.9800
O11—N151.233 (3)C22—C271.395 (3)
O12—N151.230 (3)C22—C231.403 (3)
O13—N161.224 (3)C23—C241.381 (3)
O14—N161.214 (3)C23—H23A0.9500
O15—C551.484 (7)C24—C251.399 (3)
O15—H150.8400C24—H24A0.9500
O16—C561.417 (5)C25—C261.387 (3)
O16—H160.8400C25—H25A0.9500
N1—C71.329 (3)C26—C271.396 (3)
N1—C11.377 (3)C26—H26A0.9500
N2—C71.361 (3)C28—C291.479 (3)
N2—C61.393 (3)C29—C301.393 (3)
N2—C201.465 (3)C30—C311.385 (3)
N3—C131.326 (3)C30—H30A0.9500
N3—C191.386 (3)C31—C321.391 (3)
N4—C131.357 (3)C31—H31A0.9500
N4—C141.387 (3)C32—C331.391 (3)
N4—C211.466 (3)C32—H32A0.9500
N5—C121.341 (3)C33—C341.479 (3)
N5—C81.342 (3)C35—C361.393 (3)
N6—C281.327 (3)C35—C401.403 (3)
N6—C221.383 (3)C36—C371.375 (3)
N7—C281.358 (3)C36—H36A0.9500
N7—C271.388 (3)C37—C381.410 (3)
N7—C411.466 (3)C37—H37A0.9500
N8—C341.338 (3)C38—C391.373 (3)
N8—C401.373 (3)C38—H38A0.9500
N9—C341.360 (3)C39—C401.400 (3)
N9—C351.386 (3)C39—H39A0.9500
N9—C421.468 (3)C41—H41A0.9800
N10—C291.336 (3)C41—H41B0.9800
N10—C331.343 (3)C41—H41C0.9800
N11—C441.458 (3)C42—H42A0.9800
N12—C461.446 (3)C42—H42B0.9800
N13—C481.461 (4)C42—H42C0.9800
N14—C501.464 (3)C43—C481.443 (4)
N15—C521.438 (3)C43—C441.443 (4)
N16—C541.449 (3)C44—C451.374 (3)
C1—C61.402 (3)C45—C461.385 (4)
C1—C21.403 (3)C45—H45A0.9500
C2—C31.376 (3)C46—C471.388 (4)
C2—H2A0.9500C47—C481.371 (4)
C3—C41.405 (3)C47—H47A0.9500
C3—H3A0.9500C49—C541.453 (3)
C4—C51.386 (3)C49—C501.457 (3)
C4—H4A0.9500C50—C511.363 (3)
C5—C61.393 (3)C51—C521.388 (4)
C5—H5A0.9500C51—H51A0.9500
C7—C81.477 (3)C52—C531.384 (3)
C8—C91.382 (3)C53—C541.379 (3)
C9—C101.386 (3)C53—H53A0.9500
C9—H9A0.9500C55—H55A0.9800
C10—C111.388 (3)C55—H55B0.9800
C10—H10A0.9500C55—H55C0.9800
C11—C121.384 (3)C56—H56A0.9800
C11—H11A0.9500C56—H56B0.9800
C12—C131.481 (3)C56—H56C0.9800
N8—Zn—N191.75 (7)H20B—C20—H20C109.5
N8—Zn—N1075.08 (7)H20A—C20—H20C109.5
N1—Zn—N10108.41 (7)N4—C21—H21A109.5
N8—Zn—N398.26 (7)N4—C21—H21B109.5
N1—Zn—N3149.23 (7)H21A—C21—H21B109.5
N10—Zn—N3102.28 (7)N4—C21—H21C109.5
N8—Zn—N5115.86 (7)H21A—C21—H21C109.5
N1—Zn—N574.76 (7)H21B—C21—H21C109.5
N10—Zn—N5168.82 (7)N6—C22—C27109.00 (19)
N3—Zn—N574.69 (7)N6—C22—C23130.6 (2)
N8—Zn—N6148.73 (7)C27—C22—C23120.4 (2)
N1—Zn—N694.71 (7)C24—C23—C22117.2 (2)
N10—Zn—N673.85 (7)C24—C23—H23A121.4
N3—Zn—N691.64 (7)C22—C23—H23A121.4
N5—Zn—N695.34 (6)C23—C24—C25121.9 (2)
C55—O15—H15109.5C23—C24—H24A119.0
C56—O16—H16109.5C25—C24—H24A119.0
C7—N1—C1106.06 (18)C26—C25—C24121.5 (2)
C7—N1—Zn114.61 (14)C26—C25—H25A119.3
C1—N1—Zn137.37 (14)C24—C25—H25A119.3
C7—N2—C6106.22 (17)C25—C26—C27116.5 (2)
C7—N2—C20129.15 (19)C25—C26—H26A121.8
C6—N2—C20124.59 (18)C27—C26—H26A121.8
C13—N3—C19105.66 (18)N7—C27—C22106.33 (18)
C13—N3—Zn115.66 (14)N7—C27—C26131.3 (2)
C19—N3—Zn138.31 (14)C22—C27—C26122.4 (2)
C13—N4—C14106.48 (17)N6—C28—N7112.74 (18)
C13—N4—C21129.72 (19)N6—C28—C29118.63 (19)
C14—N4—C21123.71 (19)N7—C28—C29128.61 (19)
C12—N5—C8120.67 (18)N10—C29—C30121.0 (2)
C12—N5—Zn119.28 (14)N10—C29—C28111.03 (18)
C8—N5—Zn118.88 (14)C30—C29—C28127.8 (2)
C28—N6—C22105.66 (18)C31—C30—C29117.9 (2)
C28—N6—Zn112.19 (14)C31—C30—H30A121.0
C22—N6—Zn137.15 (14)C29—C30—H30A121.0
C28—N7—C27106.23 (18)C30—C31—C32120.9 (2)
C28—N7—C41129.40 (19)C30—C31—H31A119.5
C27—N7—C41124.34 (18)C32—C31—H31A119.5
C34—N8—C40106.14 (17)C33—C32—C31117.9 (2)
C34—N8—Zn114.64 (14)C33—C32—H32A121.1
C40—N8—Zn134.92 (14)C31—C32—H32A121.1
C34—N9—C35106.88 (17)N10—C33—C32120.8 (2)
C34—N9—C42129.5 (2)N10—C33—C34110.28 (18)
C35—N9—C42123.61 (19)C32—C33—C34128.9 (2)
C29—N10—C33121.41 (19)N8—C34—N9111.88 (19)
C29—N10—Zn119.74 (14)N8—C34—C33118.54 (18)
C33—N10—Zn118.83 (14)N9—C34—C33129.55 (19)
O2—N11—O3123.2 (2)N9—C35—C36131.6 (2)
O2—N11—C44118.6 (2)N9—C35—C40105.95 (18)
O3—N11—C44118.2 (2)C36—C35—C40122.4 (2)
O4—N12—O5123.0 (2)C37—C36—C35116.0 (2)
O4—N12—C46118.8 (2)C37—C36—H36A122.0
O5—N12—C46118.2 (2)C35—C36—H36A122.0
O6—N13—O7124.2 (3)C36—C37—C38122.4 (2)
O6—N13—C48116.9 (3)C36—C37—H37A118.8
O7—N13—C48118.9 (3)C38—C37—H37A118.8
O10—N14—O9123.3 (3)C39—C38—C37121.4 (2)
O10—N14—C50119.3 (3)C39—C38—H38A119.3
O9—N14—C50117.3 (3)C37—C38—H38A119.3
O12—N15—O11122.6 (2)C38—C39—C40117.2 (2)
O12—N15—C52119.1 (2)C38—C39—H39A121.4
O11—N15—C52118.2 (2)C40—C39—H39A121.4
O14—N16—O13121.9 (2)N8—C40—C39130.28 (19)
O14—N16—C54118.5 (2)N8—C40—C35109.16 (19)
O13—N16—C54119.5 (2)C39—C40—C35120.6 (2)
N1—C1—C6109.04 (18)N7—C41—H41A109.5
N1—C1—C2130.7 (2)N7—C41—H41B109.5
C6—C1—C2120.3 (2)H41A—C41—H41B109.5
C3—C2—C1117.4 (2)N7—C41—H41C109.5
C3—C2—H2A121.3H41A—C41—H41C109.5
C1—C2—H2A121.3H41B—C41—H41C109.5
C2—C3—C4121.7 (2)N9—C42—H42A109.5
C2—C3—H3A119.1N9—C42—H42B109.5
C4—C3—H3A119.1H42A—C42—H42B109.5
C5—C4—C3121.8 (2)N9—C42—H42C109.5
C5—C4—H4A119.1H42A—C42—H42C109.5
C3—C4—H4A119.1H42B—C42—H42C109.5
C4—C5—C6116.2 (2)O1—C43—C48124.1 (3)
C4—C5—H5A121.9O1—C43—C44124.5 (2)
C6—C5—H5A121.9C48—C43—C44111.3 (2)
N2—C6—C5131.3 (2)C45—C44—C43124.7 (2)
N2—C6—C1106.09 (18)C45—C44—N11116.8 (2)
C5—C6—C1122.6 (2)C43—C44—N11118.5 (2)
N1—C7—N2112.57 (18)C44—C45—C46119.2 (2)
N1—C7—C8119.42 (19)C44—C45—H45A120.4
N2—C7—C8127.94 (19)C46—C45—H45A120.4
N5—C8—C9121.4 (2)C45—C46—C47120.8 (2)
N5—C8—C7110.57 (18)C45—C46—N12118.9 (2)
C9—C8—C7128.0 (2)C47—C46—N12120.2 (2)
C8—C9—C10117.9 (2)C48—C47—C46118.9 (2)
C8—C9—H9A121.1C48—C47—H47A120.6
C10—C9—H9A121.1C46—C47—H47A120.6
C9—C10—C11120.9 (2)C47—C48—C43125.1 (2)
C9—C10—H10A119.6C47—C48—N13117.3 (2)
C11—C10—H10A119.6C43—C48—N13117.7 (2)
C12—C11—C10117.8 (2)O8—C49—C54126.8 (2)
C12—C11—H11A121.1O8—C49—C50122.0 (2)
C10—C11—H11A121.1C54—C49—C50111.14 (19)
N5—C12—C11121.4 (2)C51—C50—C49125.9 (2)
N5—C12—C13110.87 (18)C51—C50—N14118.1 (2)
C11—C12—C13127.7 (2)C49—C50—N14116.0 (2)
N3—C13—N4112.81 (19)C50—C51—C52118.0 (2)
N3—C13—C12118.74 (19)C50—C51—H51A121.0
N4—C13—C12128.44 (19)C52—C51—H51A121.0
N4—C14—C15131.5 (2)C53—C52—C51121.6 (2)
N4—C14—C19106.15 (19)C53—C52—N15118.8 (2)
C15—C14—C19122.4 (2)C51—C52—N15119.5 (2)
C16—C15—C14116.4 (2)C54—C53—C52119.7 (2)
C16—C15—H15A121.8C54—C53—H53A120.2
C14—C15—H15A121.8C52—C53—H53A120.2
C15—C16—C17121.9 (2)C53—C54—N16116.1 (2)
C15—C16—H16A119.1C53—C54—C49123.6 (2)
C17—C16—H16A119.1N16—C54—C49120.3 (2)
C18—C17—C16121.7 (2)O15—C55—H55A109.5
C18—C17—H17A119.2O15—C55—H55B109.5
C16—C17—H17A119.2H55A—C55—H55B109.5
C17—C18—C19117.3 (2)O15—C55—H55C109.5
C17—C18—H18A121.4H55A—C55—H55C109.5
C19—C18—H18A121.4H55B—C55—H55C109.5
N3—C19—C18130.7 (2)O16—C56—H56A109.5
N3—C19—C14108.90 (19)O16—C56—H56B109.5
C18—C19—C14120.4 (2)H56A—C56—H56B109.5
N2—C20—H20B109.5O16—C56—H56C109.5
N2—C20—H20A109.5H56A—C56—H56C109.5
H20B—C20—H20A109.5H56B—C56—H56C109.5
N2—C20—H20C109.5
N8—Zn—N1—C7−127.81 (15)N4—C14—C19—C18179.8 (2)
N10—Zn—N1—C7157.34 (14)C15—C14—C19—C180.3 (3)
N3—Zn—N1—C7−18.4 (2)C28—N6—C22—C271.8 (2)
N5—Zn—N1—C7−11.46 (14)Zn—N6—C22—C27−149.76 (17)
N6—Zn—N1—C782.81 (15)C28—N6—C22—C23−176.4 (2)
N8—Zn—N1—C170.9 (2)Zn—N6—C22—C2332.0 (4)
N10—Zn—N1—C1−3.9 (2)N6—C22—C23—C24178.7 (2)
N3—Zn—N1—C1−179.68 (17)C27—C22—C23—C240.7 (3)
N5—Zn—N1—C1−172.7 (2)C22—C23—C24—C251.3 (3)
N6—Zn—N1—C1−78.5 (2)C23—C24—C25—C26−1.7 (4)
N8—Zn—N3—C13113.86 (15)C24—C25—C26—C27−0.2 (4)
N1—Zn—N3—C136.2 (2)C28—N7—C27—C22−0.1 (2)
N10—Zn—N3—C13−169.71 (15)C41—N7—C27—C22178.5 (2)
N5—Zn—N3—C13−0.80 (15)C28—N7—C27—C26179.9 (2)
N6—Zn—N3—C13−95.89 (15)C41—N7—C27—C26−1.5 (4)
N8—Zn—N3—C19−58.0 (2)N6—C22—C27—N7−1.0 (2)
N1—Zn—N3—C19−165.68 (19)C23—C22—C27—N7177.38 (19)
N10—Zn—N3—C1918.4 (2)N6—C22—C27—C26179.0 (2)
N5—Zn—N3—C19−172.6 (2)C23—C22—C27—C26−2.6 (3)
N6—Zn—N3—C1992.3 (2)C25—C26—C27—N7−177.7 (2)
N8—Zn—N5—C12−96.80 (16)C25—C26—C27—C222.3 (3)
N1—Zn—N5—C12178.76 (17)C22—N6—C28—N7−1.9 (2)
N10—Zn—N5—C1270.7 (4)Zn—N6—C28—N7157.61 (14)
N3—Zn—N5—C12−4.93 (15)C22—N6—C28—C29176.65 (18)
N6—Zn—N5—C1285.32 (16)Zn—N6—C28—C29−23.8 (2)
N8—Zn—N5—C895.50 (16)C27—N7—C28—N61.3 (2)
N1—Zn—N5—C811.06 (15)C41—N7—C28—N6−177.2 (2)
N10—Zn—N5—C8−97.0 (4)C27—N7—C28—C29−177.1 (2)
N3—Zn—N5—C8−172.62 (17)C41—N7—C28—C294.4 (4)
N6—Zn—N5—C8−82.38 (16)C33—N10—C29—C300.1 (3)
N8—Zn—N6—C2824.7 (2)Zn—N10—C29—C30178.89 (16)
N1—Zn—N6—C28125.93 (15)C33—N10—C29—C28−175.87 (19)
N10—Zn—N6—C2818.11 (14)Zn—N10—C29—C282.9 (2)
N3—Zn—N6—C28−84.20 (15)N6—C28—C29—N1014.6 (3)
N5—Zn—N6—C28−158.97 (15)N7—C28—C29—N10−167.1 (2)
N8—Zn—N6—C22174.99 (18)N6—C28—C29—C30−161.0 (2)
N1—Zn—N6—C22−83.8 (2)N7—C28—C29—C3017.3 (4)
N10—Zn—N6—C22168.4 (2)N10—C29—C30—C31−0.5 (3)
N3—Zn—N6—C2266.1 (2)C28—C29—C30—C31174.7 (2)
N5—Zn—N6—C22−8.7 (2)C29—C30—C31—C320.2 (4)
N1—Zn—N8—C34−94.50 (15)C30—C31—C32—C330.5 (4)
N10—Zn—N8—C3414.09 (15)C29—N10—C33—C320.6 (3)
N3—Zn—N8—C34114.68 (15)Zn—N10—C33—C32−178.19 (17)
N5—Zn—N8—C34−168.39 (14)C29—N10—C33—C34−178.70 (19)
N6—Zn—N8—C347.5 (2)Zn—N10—C33—C342.5 (2)
N1—Zn—N8—C4058.3 (2)C31—C32—C33—N10−0.9 (3)
N10—Zn—N8—C40166.9 (2)C31—C32—C33—C34178.3 (2)
N3—Zn—N8—C40−92.5 (2)C40—N8—C34—N9−0.4 (2)
N5—Zn—N8—C40−15.6 (2)Zn—N8—C34—N9159.95 (14)
N6—Zn—N8—C40160.33 (17)C40—N8—C34—C33−178.56 (18)
N8—Zn—N10—C29172.27 (17)Zn—N8—C34—C33−18.3 (2)
N1—Zn—N10—C29−100.90 (16)C35—N9—C34—N80.5 (2)
N3—Zn—N10—C2976.87 (16)C42—N9—C34—N8−177.9 (2)
N5—Zn—N10—C293.9 (4)C35—N9—C34—C33178.4 (2)
N6—Zn—N10—C29−11.26 (15)C42—N9—C34—C330.1 (4)
N8—Zn—N10—C33−8.94 (15)N10—C33—C34—N810.4 (3)
N1—Zn—N10—C3377.89 (16)C32—C33—C34—N8−168.8 (2)
N3—Zn—N10—C33−104.34 (16)N10—C33—C34—N9−167.4 (2)
N5—Zn—N10—C33−177.3 (3)C32—C33—C34—N913.3 (4)
N6—Zn—N10—C33167.52 (17)C34—N9—C35—C36−179.9 (2)
C7—N1—C1—C6−1.4 (2)C42—N9—C35—C36−1.4 (4)
Zn—N1—C1—C6160.87 (16)C34—N9—C35—C40−0.4 (2)
C7—N1—C1—C2180.0 (2)C42—N9—C35—C40178.1 (2)
Zn—N1—C1—C2−17.7 (4)N9—C35—C36—C37179.6 (2)
N1—C1—C2—C3176.5 (2)C40—C35—C36—C370.2 (3)
C6—C1—C2—C3−1.9 (3)C35—C36—C37—C38−0.2 (4)
C1—C2—C3—C40.8 (3)C36—C37—C38—C39−0.1 (4)
C2—C3—C4—C50.6 (4)C37—C38—C39—C400.5 (4)
C3—C4—C5—C6−0.8 (3)C34—N8—C40—C39179.6 (2)
C7—N2—C6—C5177.5 (2)Zn—N8—C40—C3925.3 (4)
C20—N2—C6—C5−0.5 (4)C34—N8—C40—C350.1 (2)
C7—N2—C6—C1−0.5 (2)Zn—N8—C40—C35−154.28 (16)
C20—N2—C6—C1−178.50 (19)C38—C39—C40—N8180.0 (2)
C4—C5—C6—N2−178.1 (2)C38—C39—C40—C35−0.5 (3)
C4—C5—C6—C1−0.3 (3)N9—C35—C40—N80.2 (2)
N1—C1—C6—N21.2 (2)C36—C35—C40—N8179.7 (2)
C2—C1—C6—N2179.96 (19)N9—C35—C40—C39−179.41 (19)
N1—C1—C6—C5−177.0 (2)C36—C35—C40—C390.1 (3)
C2—C1—C6—C51.7 (3)O1—C43—C44—C45174.1 (3)
C1—N1—C7—N21.1 (2)C48—C43—C44—C45−2.3 (4)
Zn—N1—C7—N2−165.78 (14)O1—C43—C44—N11−6.9 (4)
C1—N1—C7—C8178.35 (18)C48—C43—C44—N11176.7 (2)
Zn—N1—C7—C811.4 (2)O2—N11—C44—C45143.9 (3)
C6—N2—C7—N1−0.4 (2)O3—N11—C44—C45−35.2 (3)
C20—N2—C7—N1177.5 (2)O2—N11—C44—C43−35.2 (4)
C6—N2—C7—C8−177.3 (2)O3—N11—C44—C43145.8 (3)
C20—N2—C7—C80.5 (4)C43—C44—C45—C462.0 (4)
C12—N5—C8—C91.2 (3)N11—C44—C45—C46−177.0 (2)
Zn—N5—C8—C9168.72 (17)C44—C45—C46—C47−1.5 (4)
C12—N5—C8—C7−175.97 (18)C44—C45—C46—N12175.7 (2)
Zn—N5—C8—C7−8.4 (2)O4—N12—C46—C452.0 (4)
N1—C7—C8—N5−2.2 (3)O5—N12—C46—C45−176.4 (3)
N2—C7—C8—N5174.6 (2)O4—N12—C46—C47179.1 (2)
N1—C7—C8—C9−179.1 (2)O5—N12—C46—C470.7 (4)
N2—C7—C8—C9−2.4 (4)C45—C46—C47—C481.4 (4)
N5—C8—C9—C10−1.3 (3)N12—C46—C47—C48−175.7 (2)
C7—C8—C9—C10175.3 (2)C46—C47—C48—C43−1.9 (4)
C8—C9—C10—C110.6 (4)C46—C47—C48—N13178.7 (3)
C9—C10—C11—C120.2 (4)O1—C43—C48—C47−174.2 (3)
C8—N5—C12—C11−0.4 (3)C44—C43—C48—C472.2 (4)
Zn—N5—C12—C11−167.86 (16)O1—C43—C48—N135.3 (4)
C8—N5—C12—C13176.40 (18)C44—C43—C48—N13−178.4 (2)
Zn—N5—C12—C138.9 (2)O6—N13—C48—C4739.2 (4)
C10—C11—C12—N5−0.3 (3)O7—N13—C48—C47−141.4 (3)
C10—C11—C12—C13−176.5 (2)O6—N13—C48—C43−140.3 (3)
C19—N3—C13—N4−0.3 (2)O7—N13—C48—C4339.1 (4)
Zn—N3—C13—N4−174.72 (14)O8—C49—C50—C51171.5 (2)
C19—N3—C13—C12−179.71 (18)C54—C49—C50—C51−5.4 (4)
Zn—N3—C13—C125.9 (2)O8—C49—C50—N14−7.1 (4)
C14—N4—C13—N30.4 (2)C54—C49—C50—N14175.9 (2)
C21—N4—C13—N3177.0 (2)O10—N14—C50—C51118.4 (4)
C14—N4—C13—C12179.7 (2)O9—N14—C50—C51−63.8 (4)
C21—N4—C13—C12−3.7 (4)O10—N14—C50—C49−62.8 (4)
N5—C12—C13—N3−9.7 (3)O9—N14—C50—C49115.0 (3)
C11—C12—C13—N3166.9 (2)C49—C50—C51—C523.8 (4)
N5—C12—C13—N4171.1 (2)N14—C50—C51—C52−177.6 (2)
C11—C12—C13—N4−12.4 (4)C50—C51—C52—C53−0.2 (4)
C13—N4—C14—C15179.2 (2)C50—C51—C52—N15177.6 (2)
C21—N4—C14—C152.3 (4)O12—N15—C52—C530.7 (4)
C13—N4—C14—C19−0.3 (2)O11—N15—C52—C53179.3 (2)
C21—N4—C14—C19−177.1 (2)O12—N15—C52—C51−177.2 (2)
N4—C14—C15—C16−178.9 (2)O11—N15—C52—C511.4 (3)
C19—C14—C15—C160.4 (3)C51—C52—C53—C54−1.0 (4)
C14—C15—C16—C17−0.4 (4)N15—C52—C53—C54−178.8 (2)
C15—C16—C17—C18−0.4 (4)C52—C53—C54—N16177.6 (2)
C16—C17—C18—C191.1 (4)C52—C53—C54—C49−1.3 (4)
C13—N3—C19—C18−179.5 (2)O14—N16—C54—C53−159.6 (3)
Zn—N3—C19—C18−7.2 (4)O13—N16—C54—C5316.6 (4)
C13—N3—C19—C140.2 (2)O14—N16—C54—C4919.3 (4)
Zn—N3—C19—C14172.53 (16)O13—N16—C54—C49−164.5 (2)
C17—C18—C19—N3178.6 (2)O8—C49—C54—C53−172.7 (2)
C17—C18—C19—C14−1.1 (3)C50—C49—C54—C534.1 (3)
N4—C14—C19—N30.1 (2)O8—C49—C54—N168.5 (4)
C15—C14—C19—N3−179.5 (2)C50—C49—C54—N16−174.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O15—H15···O1i0.841.942.756 (4)165
C31—H31A···O2i0.952.533.204 (3)128
C42—H42A···O1i0.982.323.106 (3)137
C55—H55C···O9ii0.982.563.415 (7)146
C11—H11A···O11iii0.952.393.207 (3)144
C10—H10A···O3iv0.952.373.233 (3)152
C4—H4A···O4v0.952.503.333 (3)146
C37—H37A···O11vi0.952.493.314 (3)146
C10—H10A···O10vii0.952.573.133 (4)118
C20—H20B···O14vii0.982.422.949 (3)113
Symmetry codes: (i) x, y, z+1; (ii) x, y+1, z; (iii) x+1, y+1, z−1; (iv) x+1, y, z; (v) −x, −y+1, −z+1; (vi) −x+1, −y, −z+2; (vii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula[Zn(C21H17N5)2](C6H2N3O7)2·2CH4O
Mr1264.46
Crystal system, space groupTriclinic, P1
Temperature (K)153
a, b, c (Å)13.2007 (3), 13.8024 (3), 16.2009 (3)
α, β, γ (°)80.811 (1), 71.012 (1), 88.538 (1)
V (Å3)2754.28 (10)
Z2
Radiation typeMo Kα
µ (mm−1)0.54
Crystal size (mm)0.38 × 0.36 × 0.30
Data collection
DiffractometerBruker APEXII area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.816, 0.852
No. of measured, independent and
observed [I > 2σ(I)] reflections		22669, 10148, 9024
Rint0.017
(sin θ/λ)max (Å−1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.111, 1.07
No. of reflections10148
No. of parameters811
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.78, −0.51

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O15—H15···O1i0.841.942.756 (4)165.3
C31—H31A···O2i0.952.533.204 (3)128.1
C42—H42A···O1i0.982.323.106 (3)136.6
C55—H55C···O9ii0.982.563.415 (7)146.0
C11—H11A···O11iii0.952.393.207 (3)143.8
C10—H10A···O3iv0.952.373.233 (3)151.6
C4—H4A···O4v0.952.503.333 (3)146.3
C37—H37A···O11vi0.952.493.314 (3)145.6
C10—H10A···O10vii0.952.573.133 (4)118.0
C20—H20B···O14vii0.982.422.949 (3)113.4
Symmetry codes: (i) x, y, z+1; (ii) x, y+1, z; (iii) x+1, y+1, z−1; (iv) x+1, y, z; (v) −x, −y+1, −z+1; (vi) −x+1, −y, −z+2; (vii) −x+1, −y+1, −z+1.
 

Acknowledgements

The authors acknowledge financial support and a grant from the `Qing Lan' Talent Engineering Funds of Lanzhou Jiaotong University. A grant from `Long Yuan Qing Nian' of Gansu Province is also acknowledged.

References

First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
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 First citationHuang, X., Kou, F., Qi, B., Meng, X. & Wu, H. (2010). Acta Cryst. E66, m967.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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 First citationLiu, H. Y., Wu, H., Yang, J., Liu, Y. Y., Liu, B., Liu, Y. Y. & Ma, J. F. (2011). Cryst. Growth Des. 11, 2920–2927.  Web of Science CSD CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (1996). 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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ISSN: 2056-9890
Volume 68| Part 8| August 2012| Page m1072
https://doi.org/10.1107/S1600536812031443
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