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Acta Cryst. (2007). E63, m1741    [ doi:10.1107/S1600536807024087 ]

Iodido[tris(1-methylbenzimidazol-2-ylmethyl)amine]zinc(II) perchlorate dimethylformamide hemisolvate

H.-L. Wu, B. Qi, W.-B. Lv, P. Liu and J.-G. Liu

Abstract top

In the cation of the title compound, [ZnI(C27H27N7)]ClO4·0.5C3H7NO, the ZnII ion is chelated by a tris(1-methylbenzimidazol-2-ylmethyl)amine (Mentb) ligand with an I atom completing the coordination. The five-coordinate N4I ligand set may be best described as trigonal-bipyramidal, with approximate C3 molecular site symmetry.

Comment top

The asymmetric unit of the title compound, (Fig. 1), consists of a [Zn(Mentb)(I)] cation, a perchlorate anion and half a DMF molecule. The perchlorate anions is disordered and the DMF solvent is half occupancy. The ZnII ion is five-coordinate with a N4I ligand set. The Mentb ligand acts as a tetradentate N-donor, and an iodide completes the coordination. The coordination geometry of the ZnII may be best described as trigonal-bipyramidal, with approximate C3 molecular site symmetry. This geometry is assumed by the ZnII to relieve the steric crowding. The equatorial plane is occupied by three N atoms of three benzimidazolyl groups, while the ZnII atom protrudes towards I and is 0.563 (5) Å from the plane of atoms N2/N4/N6. The axial sites are occupyied by N1 and I1, with Zn1—N1 2.442 (5) Å, Zn1—I1 2.6148 (10) Å and N1—Zn1—I1 is 179.50 (13)°. The three benzimidazole ring arms of the Mentb ligand form a cone-shaped cavity. The angles N2—Zn1—N6, N2—Zn1—N4 and N4—Zn1—N6 are 115.2 (2), 110.7 (2) and 112.9 (2) °, respectively. The N1—Zn1—N2 74.6 (2), N1—Zn1—N4 73.9 (2) and N1—Zn1—N6, 74.2 (2)° angles, which are all ca 16 ° less than the ideal value of 90°, are imposed by the geometry of the Mentb ligand. The bond angles and distance in the three benzimidazole groups are equal within experimental error. In the crystal structure, there are weak π···π stacking interactions with a centroid···centroid distance of 3.542 (6)Å bewteen inversion related molecules (see Fig. 2). Some references related to the title compound are Pandey et al. (1992), Addison et al. (1981) & Wu et al., (2006).

Related literature top

For related literature see: Pandey et al., 1992; Addison et al., 1981; Wu et al., 2006; Athimoolam et al. (2005); Cox et al. (2003); Mohamed et al. (2003); Spek (2003); Stähler et al. (2001).

Experimental top

To a stired solution of tris(N-methylbenzimidazol-2-ylmethyl)amine (0.0899 g, 0.2 mmol) in hot MeOH (10 ml) was added Zn(ClO4)2.6(H2O) (0.0745 g, 0.2 mmol), followed by a solution of sodium iodide (0.0301 g, 0.2 mmol) in MeOH (5 ml). A colorless crystalline product formed rapidly. The precipitate was filtered off, washed with MeOH and absolute Et2O, and dried in vacuo. The dried precipitate was dissolved in DMF to form a colorless solution that was allowed to evaporate at room temperature. Colorless crystals suitable for X-ray diffraction studies were obtained after one week. Yield, 0.101 g (65%). (found: C, 44.32; H, 3.77; N,13.58; Zn, 8.23. Calcd. for C28.5 H30.5 Cl I N7.5 0O4.50 Zn: C, 44.01; H, 3.95; N, 13.51; Cu, 8.41%)

Refinement top

H atoms were placed in calculated positions, with C—H distances ranging from 0.93 to 0.97 Å, and treated as riding, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms. The Atoms O2/O3/O4 of the perchlorate anion are disordered over two sites with refined occupancies 0.562 (17):0.438 (17). The highest peak of 1.18 e A°-3 is 3.72Å from H27B. The SQUEEZE option in PLATON (Spek, 2003) indicated there was a solvent cavity of volume 599 Å3 containing approximately 90 electrons (possibly additional disordered DMF). In the final cycles of refinement, this contribution to the electron density was removed from the observed data. The density, the F(000) value, the molecular weight and the formula are given without taking into account the results obtained with the SQUEEZE option PLATON (Spek, 2003). Similar treatments of disordered solvent molecules were carried out by Stähler et al. (2001), Cox et al. (2003), Mohamed et al. (2003) and Athimoolam et al. (2005).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1996); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probabilty level. The major component of disorder is shown with open bonds.
[Figure 2] Fig. 2. Partial packing plot of title compound. H atoms are omitted for clarity.
Iodido[tris(1-methylbenzimidazol-2-ylmethyl)amine]zinc(II) perchlorate dimethylformamide hemisolvate top
Crystal data top
[ZnI(C27H27N7)]ClO4·0.5C3H7NOZ = 2
Mr = 777.82F(000) = 780
Triclinic, P1Dx = 1.229 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.743 (2) ÅCell parameters from 3637 reflections
b = 14.399 (3) Åθ = 2.2–23.8°
c = 14.554 (3) ŵ = 1.42 mm−1
α = 97.562 (2)°T = 298 K
β = 112.766 (2)°Block, colourless
γ = 114.420 (2)°0.50 × 0.42 × 0.39 mm
V = 2102.7 (7) Å3
Data collection top
Bruker SMART CCD
diffractometer		7231 independent reflections
Radiation source: fine-focus sealed tube4303 reflections with I > 2σ(I)
graphiteRint = 0.020
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −15→11
Tmin = 0.537, Tmax = 0.608k = −17→16
10873 measured reflectionsl = −17→15
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)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.245H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.1343P)2 + 1.7701P]
where P = (Fo2 + 2Fc2)/3
7231 reflections(Δ/σ)max < 0.001
443 parametersΔρmax = 1.18 e Å−3
251 restraintsΔρmin = −0.56 e Å−3
Crystal data top
[ZnI(C27H27N7)]ClO4·0.5C3H7NOγ = 114.420 (2)°
Mr = 777.82V = 2102.7 (7) Å3
Triclinic, P1Z = 2
a = 12.743 (2) ÅMo Kα radiation
b = 14.399 (3) ŵ = 1.42 mm−1
c = 14.554 (3) ÅT = 298 K
α = 97.562 (2)°0.50 × 0.42 × 0.39 mm
β = 112.766 (2)°
Data collection top
Bruker SMART CCD
diffractometer		7231 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		4303 reflections with I > 2σ(I)
Tmin = 0.537, Tmax = 0.608Rint = 0.020
10873 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.069H-atom parameters constrained
wR(F2) = 0.245Δρmax = 1.18 e Å−3
S = 1.09Δρmin = −0.56 e Å−3
7231 reflectionsAbsolute structure: ?
443 parametersFlack parameter: ?
251 restraintsRogers parameter: ?
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
xyzUiso*/UeqOcc. (<1)
Zn10.17757 (8)0.33681 (6)0.18237 (6)0.0481 (3)
I10.01595 (6)0.30635 (5)0.25900 (5)0.0818 (3)
Cl10.3784 (3)0.2727 (2)0.8325 (2)0.0851 (7)
N10.3298 (5)0.3651 (4)0.1122 (4)0.0413 (12)
N20.1770 (6)0.1913 (5)0.1515 (5)0.0513 (14)
N30.2031 (7)0.0727 (5)0.0621 (6)0.0651 (18)
N40.0976 (6)0.3644 (5)0.0429 (5)0.0544 (15)
N50.1150 (8)0.4303 (5)−0.0832 (5)0.0645 (18)
N60.3567 (6)0.4701 (5)0.2979 (5)0.0512 (14)
N70.5753 (6)0.5621 (5)0.3815 (5)0.0620 (17)
N80.605 (3)0.132 (2)0.163 (2)0.185 (8)0.50
O10.4358 (8)0.2947 (6)0.7669 (6)0.112 (2)
O20.2766 (19)0.1658 (11)0.7939 (17)0.129 (6)0.438 (17)
O30.4796 (17)0.293 (2)0.9358 (12)0.121 (5)0.438 (17)
O40.338 (2)0.3502 (16)0.8425 (17)0.111 (5)0.438 (17)
O2'0.344 (2)0.1694 (10)0.8390 (15)0.126 (5)0.562 (17)
O3'0.4773 (15)0.3486 (14)0.9443 (9)0.127 (5)0.562 (17)
O4'0.2711 (15)0.2913 (17)0.8095 (13)0.114 (4)0.562 (17)
O50.539 (2)0.2270 (18)0.2079 (14)0.150 (6)0.50
C10.2863 (9)0.2584 (6)0.0460 (7)0.065 (2)
H1A0.36140.25610.04630.077*
H1B0.22410.2435−0.02660.077*
C20.3133 (8)0.4366 (6)0.0547 (7)0.062 (2)
H2A0.33920.42940.00080.074*
H2B0.36980.51140.10300.074*
C30.4577 (8)0.4139 (7)0.2062 (7)0.065 (2)
H3A0.52630.45820.19120.078*
H3B0.47350.35720.22580.078*
C40.2216 (7)0.1737 (6)0.0867 (6)0.0548 (18)
C50.1431 (8)0.0209 (6)0.1158 (7)0.064 (2)
C60.1256 (7)0.0941 (6)0.1728 (6)0.058 (2)
C70.0668 (9)0.0654 (7)0.2332 (7)0.071 (2)
H70.05300.11320.26990.085*
C80.0284 (10)−0.0386 (8)0.2375 (8)0.086 (3)
H8−0.0109−0.06110.27870.104*
C90.0480 (12)−0.1097 (8)0.1807 (10)0.098 (4)
H90.0194−0.17920.18460.118*
C100.1049 (10)−0.0841 (7)0.1219 (10)0.090 (3)
H100.1190−0.13240.08640.108*
C110.2406 (11)0.0263 (8)−0.0060 (8)0.088 (3)
H11A0.32640.03610.03650.133*
H11B0.24320.0621−0.05700.133*
H11C0.1772−0.0500−0.04250.133*
C120.1750 (8)0.4097 (6)0.0041 (6)0.0538 (18)
C13−0.0117 (11)0.3958 (7)−0.1021 (7)0.074 (3)
C14−0.0247 (8)0.3530 (6)−0.0231 (6)0.060 (2)
C15−0.1424 (9)0.3112 (7)−0.0193 (7)0.070 (2)
H15−0.15160.28390.03330.084*
C16−0.2467 (11)0.3130 (9)−0.1009 (9)0.095 (3)
H16−0.32760.2856−0.10210.114*
C17−0.2336 (13)0.3533 (10)−0.1780 (9)0.095 (3)
H17−0.30590.3514−0.23080.114*
C18−0.1203 (13)0.3951 (9)−0.1793 (8)0.092 (3)
H18−0.11290.4240−0.23140.111*
C190.1741 (12)0.4828 (9)−0.1429 (8)0.094 (3)
H19A0.14490.5325−0.16210.141*
H19B0.14800.4287−0.20600.141*
H19C0.26860.5219−0.10000.141*
C200.4631 (8)0.4824 (6)0.2959 (6)0.0554 (18)
C210.5376 (9)0.6073 (7)0.4445 (6)0.062 (2)
C220.4016 (8)0.5502 (6)0.3924 (6)0.0543 (18)
C230.3320 (9)0.5747 (7)0.4340 (6)0.062 (2)
H230.24020.53670.39950.075*
C240.4090 (12)0.6613 (8)0.5328 (8)0.083 (3)
H240.36600.68070.56370.100*
C250.5447 (12)0.7178 (9)0.5846 (8)0.092 (3)
H250.59170.77460.64900.110*
C260.6109 (11)0.6908 (8)0.5418 (7)0.085 (3)
H260.70270.72750.57700.102*
C270.7098 (9)0.5979 (9)0.4038 (9)0.091 (3)
H27A0.73840.65560.37690.136*
H27B0.71320.53810.37000.136*
H27C0.76670.62360.47910.136*
C280.564 (4)0.158 (3)0.226 (2)0.198 (9)0.50
H280.55610.12700.27660.238*0.50
C290.630 (4)0.044 (3)0.183 (3)0.207 (10)0.50
H29A0.72330.07040.21470.310*0.50
H29B0.5847−0.01510.11690.310*0.50
H29C0.59880.01800.22990.310*0.50
C300.607 (4)0.150 (3)0.066 (3)0.205 (10)0.50
H30A0.60910.21730.06400.308*0.50
H30B0.52900.09130.00420.308*0.50
H30C0.68380.15370.06590.308*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0486 (5)0.0468 (5)0.0512 (5)0.0267 (4)0.0244 (4)0.0156 (4)
I10.0762 (5)0.0963 (5)0.0871 (5)0.0451 (4)0.0503 (4)0.0340 (4)
Cl10.0785 (15)0.0850 (16)0.1106 (19)0.0383 (13)0.0627 (15)0.0453 (14)
N10.040 (3)0.032 (3)0.040 (3)0.015 (2)0.013 (2)0.008 (2)
N20.051 (3)0.049 (3)0.056 (4)0.030 (3)0.024 (3)0.017 (3)
N30.059 (4)0.052 (4)0.075 (5)0.032 (3)0.026 (4)0.004 (3)
N40.059 (4)0.050 (4)0.053 (4)0.032 (3)0.023 (3)0.016 (3)
N50.086 (5)0.058 (4)0.064 (4)0.044 (4)0.039 (4)0.028 (3)
N60.052 (4)0.048 (3)0.052 (4)0.028 (3)0.022 (3)0.019 (3)
N70.050 (4)0.064 (4)0.056 (4)0.025 (3)0.015 (3)0.024 (3)
N80.165 (12)0.217 (15)0.128 (11)0.135 (11)0.018 (10)−0.026 (12)
O10.104 (4)0.131 (5)0.117 (5)0.051 (4)0.076 (4)0.048 (4)
O20.103 (7)0.116 (7)0.136 (8)0.037 (7)0.047 (7)0.046 (7)
O30.104 (7)0.127 (8)0.122 (7)0.042 (7)0.058 (6)0.065 (7)
O40.107 (7)0.109 (7)0.124 (7)0.054 (6)0.065 (6)0.039 (6)
O2'0.120 (7)0.107 (6)0.134 (7)0.049 (6)0.050 (6)0.061 (6)
O3'0.110 (6)0.113 (7)0.124 (7)0.025 (6)0.059 (6)0.044 (6)
O4'0.101 (7)0.121 (7)0.125 (7)0.059 (6)0.056 (6)0.041 (6)
O50.162 (11)0.178 (13)0.104 (9)0.143 (10)0.014 (9)−0.002 (9)
C10.073 (5)0.063 (5)0.072 (5)0.041 (5)0.043 (5)0.020 (4)
C20.073 (5)0.053 (4)0.069 (5)0.032 (4)0.043 (5)0.026 (4)
C30.054 (5)0.068 (5)0.079 (6)0.032 (4)0.038 (4)0.026 (4)
C40.049 (4)0.052 (4)0.063 (5)0.029 (4)0.025 (4)0.016 (4)
C50.049 (4)0.044 (4)0.072 (5)0.019 (4)0.014 (4)0.005 (4)
C60.046 (4)0.044 (4)0.058 (5)0.018 (4)0.009 (4)0.013 (4)
C70.074 (6)0.055 (5)0.064 (5)0.024 (4)0.027 (5)0.017 (4)
C80.075 (6)0.060 (6)0.087 (7)0.015 (5)0.025 (5)0.030 (5)
C90.107 (9)0.045 (5)0.113 (9)0.027 (6)0.039 (7)0.031 (6)
C100.081 (7)0.050 (6)0.119 (9)0.034 (5)0.033 (7)0.024 (6)
C110.092 (7)0.077 (6)0.091 (7)0.050 (6)0.040 (6)0.002 (5)
C120.072 (5)0.042 (4)0.052 (4)0.032 (4)0.031 (4)0.016 (3)
C130.105 (8)0.055 (5)0.058 (5)0.052 (5)0.025 (5)0.019 (4)
C140.069 (5)0.045 (4)0.058 (5)0.036 (4)0.019 (4)0.008 (4)
C150.066 (5)0.066 (5)0.080 (6)0.043 (5)0.028 (5)0.019 (4)
C160.082 (7)0.083 (7)0.102 (8)0.056 (6)0.018 (6)0.016 (6)
C170.100 (8)0.110 (9)0.093 (8)0.080 (8)0.031 (7)0.045 (7)
C180.121 (9)0.096 (8)0.070 (6)0.081 (8)0.027 (6)0.027 (5)
C190.122 (9)0.102 (8)0.085 (7)0.066 (7)0.056 (7)0.059 (6)
C200.052 (4)0.053 (4)0.066 (5)0.031 (4)0.027 (4)0.028 (4)
C210.070 (6)0.060 (5)0.049 (5)0.034 (5)0.020 (4)0.025 (4)
C220.065 (5)0.053 (4)0.046 (4)0.035 (4)0.021 (4)0.023 (3)
C230.069 (5)0.065 (5)0.048 (4)0.038 (4)0.022 (4)0.016 (4)
C240.117 (9)0.082 (7)0.064 (6)0.058 (7)0.046 (6)0.030 (5)
C250.100 (8)0.090 (7)0.050 (5)0.045 (7)0.013 (6)0.010 (5)
C260.076 (6)0.082 (7)0.056 (6)0.031 (6)0.006 (5)0.023 (5)
C270.056 (5)0.104 (8)0.093 (7)0.036 (5)0.022 (5)0.041 (6)
C280.176 (12)0.224 (15)0.124 (11)0.121 (12)0.018 (11)−0.030 (12)
C290.186 (13)0.214 (16)0.143 (13)0.125 (13)0.012 (12)−0.012 (13)
C300.180 (13)0.219 (16)0.133 (12)0.108 (13)0.014 (13)−0.002 (13)
Geometric parameters (Å, °) top
Zn1—N42.064 (6)C6—C71.362 (12)
Zn1—N62.069 (6)C7—C81.388 (12)
Zn1—N22.080 (6)C7—H70.9300
Zn1—N12.442 (5)C8—C91.393 (16)
Zn1—I12.6148 (10)C8—H80.9300
Cl1—O21.387 (11)C9—C101.318 (16)
Cl1—O2'1.394 (10)C9—H90.9300
Cl1—O11.406 (6)C10—H100.9300
Cl1—O4'1.423 (10)C11—H11A0.9600
Cl1—O41.426 (12)C11—H11B0.9600
Cl1—O31.442 (12)C11—H11C0.9600
Cl1—O3'1.495 (11)C13—C181.400 (14)
N1—C21.440 (9)C13—C141.407 (12)
N1—C11.445 (9)C14—C151.393 (12)
N1—C31.448 (9)C15—C161.412 (13)
N2—C41.322 (9)C15—H150.9300
N2—C61.414 (9)C16—C171.364 (16)
N3—C41.347 (9)C16—H160.9300
N3—C51.377 (11)C17—C181.323 (16)
N3—C111.455 (11)C17—H170.9300
N4—C121.308 (10)C18—H180.9300
N4—C141.403 (10)C19—H19A0.9600
N5—C121.350 (10)C19—H19B0.9600
N5—C131.374 (12)C19—H19C0.9600
N5—C191.450 (11)C21—C221.377 (11)
N6—C201.306 (10)C21—C261.387 (13)
N6—C221.405 (9)C22—C231.377 (11)
N7—C201.343 (10)C23—C241.417 (12)
N7—C211.392 (11)C23—H230.9300
N7—C271.450 (11)C24—C251.374 (15)
N8—C281.298 (19)C24—H240.9300
N8—C291.473 (19)C25—C261.365 (15)
N8—C301.474 (19)C25—H250.9300
O5—C281.197 (19)C26—H260.9300
C1—C41.501 (11)C27—H27A0.9600
C1—H1A0.9700C27—H27B0.9600
C1—H1B0.9700C27—H27C0.9600
C2—C121.468 (11)C28—H280.9300
C2—H2A0.9700C29—H29A0.9600
C2—H2B0.9700C29—H29B0.9600
C3—C201.490 (11)C29—H29C0.9600
C3—H3A0.9700C30—H30A0.9600
C3—H3B0.9700C30—H30B0.9600
C5—C61.398 (11)C30—H30C0.9600
C5—C101.411 (12)
N4—Zn1—N6112.9 (2)C6—C7—H7121.6
N4—Zn1—N2110.7 (2)C8—C7—H7121.6
N6—Zn1—N2115.2 (2)C7—C8—C9120.8 (10)
N4—Zn1—N173.9 (2)C7—C8—H8119.6
N6—Zn1—N174.2 (2)C9—C8—H8119.6
N2—Zn1—N174.6 (2)C10—C9—C8123.7 (9)
N4—Zn1—I1106.57 (19)C10—C9—H9118.2
N6—Zn1—I1105.53 (17)C8—C9—H9118.2
N2—Zn1—I1105.19 (17)C9—C10—C5116.2 (10)
N1—Zn1—I1179.50 (13)C9—C10—H10121.9
O2—Cl1—O2'34.7 (9)C5—C10—H10121.9
O2—Cl1—O1112.7 (9)N3—C11—H11A109.5
O2'—Cl1—O1112.6 (8)N3—C11—H11B109.5
O2—Cl1—O4'81.0 (10)H11A—C11—H11B109.5
O2'—Cl1—O4'110.6 (9)N3—C11—H11C109.5
O1—Cl1—O4'115.5 (7)H11A—C11—H11C109.5
O2—Cl1—O4113.4 (10)H11B—C11—H11C109.5
O2'—Cl1—O4138.0 (10)N4—C12—N5113.1 (7)
O1—Cl1—O4105.5 (8)N4—C12—C2121.8 (7)
O4'—Cl1—O432.9 (8)N5—C12—C2125.1 (7)
O2—Cl1—O3108.3 (10)N5—C13—C18134.0 (10)
O2'—Cl1—O376.0 (10)N5—C13—C14107.0 (7)
O1—Cl1—O3108.1 (9)C18—C13—C14119.0 (11)
O4'—Cl1—O3127.4 (11)C15—C14—N4131.5 (8)
O4—Cl1—O3108.6 (10)C15—C14—C13121.6 (8)
O2—Cl1—O3'130.3 (10)N4—C14—C13106.9 (8)
O2'—Cl1—O3'104.4 (8)C14—C15—C16115.4 (10)
O1—Cl1—O3'109.7 (7)C14—C15—H15122.3
O4'—Cl1—O3'103.1 (9)C16—C15—H15122.3
O4—Cl1—O3'77.8 (10)C17—C16—C15122.6 (11)
O3—Cl1—O3'31.9 (10)C17—C16—H16118.7
C2—N1—C1114.2 (6)C15—C16—H16118.7
C2—N1—C3114.5 (6)C18—C17—C16121.4 (10)
C1—N1—C3113.6 (6)C18—C17—H17119.3
C2—N1—Zn1103.2 (4)C16—C17—H17119.3
C1—N1—Zn1105.8 (4)C17—C18—C13120.0 (11)
C3—N1—Zn1103.9 (4)C17—C18—H18120.0
C4—N2—C6106.1 (6)C13—C18—H18120.0
C4—N2—Zn1117.3 (5)N5—C19—H19A109.5
C6—N2—Zn1136.1 (5)N5—C19—H19B109.5
C4—N3—C5106.7 (7)H19A—C19—H19B109.5
C4—N3—C11127.5 (8)N5—C19—H19C109.5
C5—N3—C11125.8 (7)H19A—C19—H19C109.5
C12—N4—C14106.4 (7)H19B—C19—H19C109.5
C12—N4—Zn1118.0 (5)N6—C20—N7113.4 (7)
C14—N4—Zn1135.4 (6)N6—C20—C3122.3 (7)
C12—N5—C13106.6 (7)N7—C20—C3124.3 (7)
C12—N5—C19126.8 (8)C22—C21—C26121.8 (9)
C13—N5—C19126.5 (8)C22—C21—N7106.5 (7)
C20—N6—C22105.5 (6)C26—C21—N7131.7 (9)
C20—N6—Zn1117.7 (5)C21—C22—C23121.3 (7)
C22—N6—Zn1136.2 (5)C21—C22—N6108.3 (7)
C20—N7—C21106.3 (7)C23—C22—N6130.4 (7)
C20—N7—C27127.6 (8)C22—C23—C24115.9 (9)
C21—N7—C27126.1 (8)C22—C23—H23122.0
C28—N8—C29108 (3)C24—C23—H23122.0
C28—N8—C30138 (3)C25—C24—C23122.5 (10)
C29—N8—C30113 (3)C25—C24—H24118.7
N1—C1—C4110.0 (6)C23—C24—H24118.7
N1—C1—H1A109.7C26—C25—C24120.2 (10)
C4—C1—H1A109.7C26—C25—H25119.9
N1—C1—H1B109.7C24—C25—H25119.9
C4—C1—H1B109.7C25—C26—C21118.3 (10)
H1A—C1—H1B108.2C25—C26—H26120.8
N1—C2—C12110.2 (6)C21—C26—H26120.8
N1—C2—H2A109.6N7—C27—H27A109.5
C12—C2—H2A109.6N7—C27—H27B109.5
N1—C2—H2B109.6H27A—C27—H27B109.5
C12—C2—H2B109.6N7—C27—H27C109.5
H2A—C2—H2B108.1H27A—C27—H27C109.5
N1—C3—C20110.3 (6)H27B—C27—H27C109.5
N1—C3—H3A109.6O5—C28—N8109 (3)
C20—C3—H3A109.6O5—C28—H28125.4
N1—C3—H3B109.6N8—C28—H28125.4
C20—C3—H3B109.6N8—C29—H29A109.5
H3A—C3—H3B108.1N8—C29—H29B109.5
N2—C4—N3112.8 (7)H29A—C29—H29B109.5
N2—C4—C1123.0 (7)N8—C29—H29C109.5
N3—C4—C1124.2 (7)H29A—C29—H29C109.5
N3—C5—C6107.7 (7)H29B—C29—H29C109.5
N3—C5—C10131.2 (9)N8—C30—H30A109.5
C6—C5—C10121.1 (10)N8—C30—H30B109.5
C7—C6—C5121.3 (8)H30A—C30—H30B109.5
C7—C6—N2131.9 (8)N8—C30—H30C109.5
C5—C6—N2106.7 (7)H30A—C30—H30C109.5
C6—C7—C8116.8 (9)H30B—C30—H30C109.5
Acknowledgements top

The authors acknowledge the financial support of Lanzhou Jiaotong University and a grant from the Qing Lan Talent Engineering Funds. A grant from the Middle-Young Age Science Foundation of Gansu Province (grant No. 3YS061-A25–023) is also acknowledged.

references
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