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Acta Cryst. (2007). E63, m1812    [ doi:10.1107/S1600536807025263 ]

cis-Bis(dicyanamido)bis(4,4'-dimethyl-2,2'-bipyridyl)zinc(II) ethanol hemisolvate

X.-Z. Li, L.-N. Zhu, H. Qu, D.-D. Xu and D.-M. Kong

Abstract top

In the title compound, [Zn(C2N3)2(C12H12N2)2]·0.5C2H6O, the Zn atom is in a distorted octahedral environment formed by six N atoms from two 4,4'-dimethyl-2,2'-bipyridine (dmbpy) ligands and two dicyanamide ligands that are cis to one another. There are weak [pi]-[pi] interactions between the dmbpy ligands in adjacent molecules [with centroid-centroid distances of 4.175 (3) and 3.838 (3) Å]. One dicyanamide ligand is disordered over two positions with occupancies 0.64 (2):0.36 (2). The ethanol molecule has a half-occupancy.

Comment top

Polypyridine complexes of transition metals have received much attention in recent years on account of their photophysical properties (Yiting et al., 2001). Hydrogen bonds and π···π stacking interactions have also proven to play important roles in the control of molecular arrangement in the crystalline state and the properties of matter (Jones & Rao, 2001).

The crystal structure of (I) contains half an ethanol molecule for each zinc(II) complex. The Zn atom is coordinated by six N atoms from two chelating dmbpy ligands and two dca ligands that are cis to one another (Fig.1). The Zn—N bond distances range from 2.101 (4) to 2.226 (3) Å and the cis N—Zn—N angles range from 74.87 (13) to 96.25 (13) °, indicating a distorted octahedral coordinated geometry around Zn atom. The dmbpy ligands are planar (maximum deviation from the least-squares planes are 0.0499 (44) Å (for the ligand containing N1 and 0.0436 (50) Å for the ligand containing N3.

The dihedral angle between the two dmbpy ligands is 79.31 (7) °. in the two dca ligands, all the C—N triple bond distances less than 1.13 Å. As depicted in Fig. 2, the complexes are linked via weak π···π stacking interactions between parallel dmbpy ligands to generate a one-dimensional chain along the [100] direction. The center-to-center distance between the pyridyl ring containing atom N1 and that containing N2i atom (i = 1 − x, 1 − y, 1 − z) is 4.175 (3) Å and that between the rings containing atom N3 and atom N4ii (ii = − x, 1 − y, −z) is 3.838 (3) Å. The one-dimensional chains are parallel in the crystal structure of (I) and the ethanol resides in a vacancy between the main complexes.

Related literature top

For related literature, see: Jones & Rao (2001); Yiting et al. (2001).

Experimental top

An ethanol solution (20 ml) of dmbpy (36.8 mg, 0.2 mmol) was added to a mixed aqueous solution (10 ml) of the hexahydrate of zinc(II) perchlorate (37.2 mg, 0.1 mmol) and sodium dicyanamide (17.8 mg, 0.2 mmol) under continuous stirring. After 30 min, the reaction mixture was filtered. Colorless crystals of (I) suitable for X-ray diffraction analysis were obtained by slow evaporation of the filtrate at room temperature. Yield 67%. Spectroscopic analysis: IR (KBr, νcm−1): 3433, 2295, 2231, 2200,2170, 1616, 1562, 1485, 1354, 1120, 1016, 921, 837. (IR spectra were recorded on a BIO-RAD FTS 3000 infrared spectrophotometer). Analysis, required for C58H54N20OZn2: C 59.14, H 4.62, N 23.78%; found: C 59.32, H 4.39, N 23.85%.

Refinement top

The dca ligand containing atom N8 is disordered over two positions with refined site-occupancy factors of 0.64 (2) and 0.36 (2). All H atoms were located in a difference Fourier map and were refined using a riding model, with distances between 0.93–0.97 Å (CH) and an OH distance of 0.82 Å. Uiso(H) values were set to either 1.2Ueq or 1.5Ueq (CH3, OH) of the attached atom.

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: APEX2 or SAINT? (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker 2003); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. View of the assymmetric unit of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The molecular packing, viewed along c axis.
cis-Bis(4,4'-dimethyl-2,2'-bipyridyl)bis(dicyanamide)zinc(II) ethanol hemisolvate top
Crystal data top
[Zn(C2N3)2(C12H12N2)2]·0.5C2H6OF000 = 1220
Mr = 589.00Dx = 1.322 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5956 reflections
a = 15.694 (2) Åθ = 2.8–25.4º
b = 14.713 (2) ŵ = 0.87 mm−1
c = 13.8868 (19) ÅT = 294 (2) K
β = 112.674 (2)ºBlock, colourless
V = 2958.7 (7) Å30.24 × 0.20 × 0.16 mm
Z = 4
Data collection top
Bruker APEX II CCD area-detector
diffractometer		6059 independent reflections
Radiation source: fine-focus sealed tube4171 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.031
T = 294(2) Kθmax = 26.4º
φ and ω scansθmin = 1.4º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −19→9
Tmin = 0.772, Tmax = 0.870k = −18→17
16800 measured reflectionsl = −17→17
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)] = 0.057H-atom parameters constrained
wR(F2) = 0.206  w = 1/[σ2(Fo2) + (0.1227P)2 + 1.4831P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.003
6059 reflectionsΔρmax = 0.95 e Å−3
402 parametersΔρmin = −0.45 e Å−3
64 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Zn(C2N3)2(C12H12N2)2]·0.5C2H6OV = 2958.7 (7) Å3
Mr = 589.00Z = 4
Monoclinic, P21/cMo Kα
a = 15.694 (2) ŵ = 0.87 mm−1
b = 14.713 (2) ÅT = 294 (2) K
c = 13.8868 (19) Å0.24 × 0.20 × 0.16 mm
β = 112.674 (2)º
Data collection top
Bruker APEX II CCD area-detector
diffractometer		6059 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4171 reflections with I > 2σ(I)
Tmin = 0.772, Tmax = 0.870Rint = 0.031
16800 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05764 restraints
wR(F2) = 0.206H-atom parameters constrained
S = 1.08Δρmax = 0.95 e Å−3
6059 reflectionsΔρmin = −0.45 e Å−3
402 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(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)
Zn10.26488 (3)0.45836 (3)0.21113 (3)0.0488 (2)
N10.3197 (2)0.5743 (2)0.3162 (3)0.0502 (8)
N20.3189 (2)0.3995 (2)0.3645 (3)0.0510 (8)
N30.1999 (2)0.5370 (2)0.0733 (3)0.0481 (8)
N40.1283 (2)0.4973 (3)0.2124 (3)0.0524 (8)
N50.3916 (3)0.4500 (3)0.1909 (3)0.0656 (10)
N60.5474 (4)0.4465 (4)0.1965 (5)0.0952 (15)
N70.6198 (5)0.5372 (4)0.1048 (5)0.1123 (19)
N80.2159 (3)0.3333 (3)0.1376 (3)0.0706 (10)
C10.3184 (3)0.6601 (3)0.2883 (4)0.0604 (11)
H10.29110.67420.21760.073*
C20.3553 (3)0.7299 (3)0.3580 (4)0.0632 (11)
H20.35330.78940.33440.076*
C30.3950 (3)0.7109 (3)0.4623 (4)0.0613 (11)
C40.3968 (3)0.6203 (3)0.4924 (3)0.0599 (11)
H40.42330.60470.56270.072*
C50.3590 (3)0.5535 (3)0.4176 (3)0.0478 (9)
C60.3579 (3)0.4568 (3)0.4447 (3)0.0493 (9)
C70.3940 (3)0.4249 (3)0.5452 (3)0.0582 (10)
H70.42130.46540.59980.070*
C80.3906 (3)0.3331 (3)0.5671 (4)0.0639 (11)
C90.3523 (3)0.2761 (3)0.4843 (4)0.0664 (12)
H90.35040.21390.49520.080*
C100.3168 (3)0.3102 (3)0.3857 (4)0.0601 (11)
H100.29000.27020.33040.072*
C110.4351 (4)0.7839 (4)0.5419 (5)0.0880 (17)
H11A0.46430.82880.51490.132*
H11B0.48000.75780.60430.132*
H11C0.38680.81180.55780.132*
C120.4267 (4)0.3001 (4)0.6780 (4)0.0894 (17)
H12A0.38170.31170.70770.134*
H12B0.48300.33160.71770.134*
H12C0.43860.23600.67960.134*
C130.2371 (3)0.5524 (3)0.0024 (3)0.0574 (11)
H130.29180.52300.01030.069*
C140.1983 (4)0.6092 (3)−0.0804 (4)0.0670 (12)
H140.22610.6174−0.12800.080*
C150.1173 (4)0.6545 (3)−0.0936 (4)0.0666 (12)
C160.0785 (3)0.6362 (3)−0.0229 (4)0.0620 (11)
H160.02280.6635−0.03060.074*
C170.1205 (3)0.5779 (3)0.0597 (3)0.0470 (9)
C180.0799 (3)0.5560 (3)0.1380 (3)0.0476 (9)
C19−0.0018 (3)0.5927 (3)0.1341 (4)0.0567 (10)
H19−0.03410.63290.08070.068*
C20−0.0367 (3)0.5707 (3)0.2085 (4)0.0625 (11)
C210.0135 (4)0.5108 (4)0.2844 (4)0.0731 (13)
H21−0.00710.49380.33630.088*
C220.0943 (4)0.4759 (4)0.2837 (4)0.0676 (12)
H220.12710.43500.33590.081*
C230.0748 (5)0.7225 (4)−0.1791 (5)0.102 (2)
H23A0.01820.6984−0.22920.153*
H23B0.11670.7350−0.21270.153*
H23C0.06210.7776−0.15010.153*
C24−0.1243 (4)0.6141 (4)0.2073 (5)0.0829 (16)
H24A−0.16880.56720.20030.124*
H24B−0.14810.65500.14910.124*
H24C−0.11210.64700.27090.124*
C250.4622 (3)0.4524 (3)0.1893 (3)0.0533 (10)
C260.5817 (4)0.4974 (4)0.1456 (5)0.0753 (14)
C270.1844 (4)0.2722 (3)0.0877 (4)0.0698 (13)
N90.1507 (7)0.2111 (7)0.0119 (11)0.088 (3)0.64 (2)
C280.0769 (4)0.1747 (4)−0.0020 (5)0.0834 (16)0.64 (2)
N100.0048 (6)0.1397 (7)−0.0195 (11)0.105 (4)0.64 (2)
N9'0.1659 (9)0.1872 (10)0.0591 (15)0.070 (5)0.36 (2)
C28'0.0769 (4)0.1747 (4)−0.0020 (5)0.0834 (16)0.36 (2)
N10'0.0058 (8)0.1591 (13)−0.0634 (15)0.094 (6)0.36 (2)
C290.7949 (9)0.0355 (7)0.9106 (12)0.096 (4)0.50
H29A0.83880.02260.87970.144*0.50
H29B0.7404−0.00050.87720.144*0.50
H29C0.82160.02120.98370.144*0.50
C300.7712 (7)0.1294 (7)0.8976 (9)0.077 (3)0.50
H30A0.70520.13460.85780.092*0.50
H30B0.78420.15590.96580.092*0.50
O10.8149 (5)0.1774 (6)0.8501 (7)0.098 (2)0.50
H1A0.83070.14390.81280.147*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0478 (3)0.0516 (3)0.0448 (3)−0.0035 (2)0.0155 (2)−0.00216 (19)
N10.055 (2)0.0476 (18)0.0453 (18)−0.0068 (15)0.0164 (15)−0.0053 (15)
N20.0515 (19)0.0518 (19)0.0479 (18)−0.0030 (15)0.0170 (15)−0.0007 (15)
N30.0490 (19)0.0537 (19)0.0415 (17)−0.0028 (15)0.0173 (15)−0.0023 (14)
N40.0475 (19)0.062 (2)0.050 (2)−0.0020 (16)0.0210 (16)0.0010 (17)
N50.057 (2)0.078 (3)0.065 (2)0.0031 (19)0.0269 (19)0.0028 (19)
N60.0927 (17)0.0955 (18)0.0974 (18)0.0011 (10)0.0367 (11)0.0035 (10)
N70.111 (2)0.114 (2)0.114 (2)0.0007 (10)0.0455 (12)0.0008 (10)
N80.0700 (13)0.0688 (13)0.0706 (13)−0.0009 (9)0.0245 (9)−0.0025 (9)
C10.072 (3)0.053 (2)0.056 (2)−0.006 (2)0.023 (2)−0.002 (2)
C20.068 (3)0.051 (2)0.066 (3)−0.007 (2)0.022 (2)−0.004 (2)
C30.054 (3)0.056 (2)0.068 (3)−0.007 (2)0.017 (2)−0.014 (2)
C40.054 (2)0.066 (3)0.049 (2)0.000 (2)0.0090 (19)−0.007 (2)
C50.043 (2)0.053 (2)0.045 (2)−0.0018 (17)0.0147 (17)−0.0053 (17)
C60.044 (2)0.055 (2)0.049 (2)0.0001 (17)0.0187 (18)0.0022 (18)
C70.058 (3)0.066 (3)0.045 (2)−0.002 (2)0.0135 (19)0.002 (2)
C80.058 (3)0.073 (3)0.059 (3)0.002 (2)0.020 (2)0.013 (2)
C90.073 (3)0.053 (2)0.075 (3)0.004 (2)0.030 (3)0.012 (2)
C100.068 (3)0.050 (2)0.062 (3)−0.006 (2)0.025 (2)−0.001 (2)
C110.092 (4)0.071 (3)0.078 (4)−0.006 (3)0.007 (3)−0.028 (3)
C120.096 (4)0.095 (4)0.068 (3)0.006 (3)0.022 (3)0.030 (3)
C130.057 (3)0.070 (3)0.049 (2)0.001 (2)0.024 (2)−0.001 (2)
C140.084 (3)0.069 (3)0.057 (3)0.000 (3)0.037 (3)0.004 (2)
C150.081 (3)0.062 (3)0.054 (3)0.000 (2)0.024 (2)0.004 (2)
C160.066 (3)0.057 (3)0.063 (3)0.009 (2)0.026 (2)0.002 (2)
C170.050 (2)0.045 (2)0.047 (2)−0.0037 (17)0.0192 (17)−0.0072 (17)
C180.045 (2)0.048 (2)0.047 (2)−0.0049 (17)0.0153 (17)−0.0085 (17)
C190.054 (2)0.057 (2)0.060 (3)0.0001 (19)0.023 (2)−0.008 (2)
C200.053 (3)0.066 (3)0.074 (3)−0.007 (2)0.031 (2)−0.014 (2)
C210.065 (3)0.091 (4)0.077 (3)−0.005 (3)0.042 (3)0.008 (3)
C220.064 (3)0.082 (3)0.064 (3)−0.003 (2)0.032 (2)0.011 (2)
C230.125 (5)0.097 (4)0.084 (4)0.032 (4)0.040 (4)0.037 (3)
C240.063 (3)0.096 (4)0.102 (4)0.002 (3)0.045 (3)−0.011 (3)
C250.045 (2)0.056 (2)0.054 (2)0.0052 (18)0.0142 (19)0.0010 (18)
C260.061 (3)0.084 (4)0.092 (4)0.006 (3)0.041 (3)0.006 (3)
C270.067 (3)0.057 (3)0.079 (3)−0.010 (2)0.021 (3)−0.016 (2)
N90.089 (3)0.088 (3)0.088 (3)−0.0007 (10)0.0342 (16)−0.0016 (10)
C280.078 (4)0.084 (4)0.091 (4)−0.009 (3)0.035 (3)−0.024 (3)
N100.105 (4)0.105 (4)0.105 (4)−0.0011 (10)0.0398 (17)−0.0005 (10)
N9'0.070 (5)0.069 (5)0.071 (5)0.0000 (10)0.026 (2)0.0000 (10)
C28'0.078 (4)0.084 (4)0.091 (4)−0.009 (3)0.035 (3)−0.024 (3)
N10'0.094 (6)0.094 (6)0.094 (6)−0.0005 (10)0.036 (2)−0.0002 (10)
C290.069 (6)0.106 (7)0.119 (8)−0.011 (5)0.041 (6)0.008 (6)
C300.055 (5)0.095 (6)0.080 (6)−0.001 (5)0.026 (4)0.003 (5)
O10.071 (4)0.098 (5)0.107 (5)0.004 (4)0.014 (4)0.040 (4)
Geometric parameters (Å, °) top
Zn1—N82.101 (4)C12—H12A0.9600
Zn1—N52.117 (4)C12—H12B0.9600
Zn1—N32.130 (3)C12—H12C0.9600
Zn1—N22.148 (3)C13—C141.360 (6)
Zn1—N12.194 (3)C13—H130.9300
Zn1—N42.226 (3)C14—C151.384 (7)
N1—C11.319 (5)C14—H140.9300
N1—C51.336 (5)C15—C161.367 (6)
N2—C61.342 (5)C15—C231.498 (7)
N2—C101.349 (5)C16—C171.380 (6)
N3—C171.330 (5)C16—H160.9300
N3—C131.342 (5)C17—C181.492 (5)
N4—C221.331 (6)C18—C191.373 (6)
N4—C181.336 (5)C19—C201.382 (6)
N5—C251.118 (6)C19—H190.9300
N6—C261.281 (7)C20—C211.366 (7)
N6—C251.305 (7)C20—C241.510 (6)
N7—C261.132 (7)C21—C221.372 (7)
N8—C271.127 (6)C21—H210.9300
C1—C21.377 (6)C22—H220.9300
C1—H10.9300C23—H23A0.9600
C2—C31.367 (7)C23—H23B0.9600
C2—H20.9300C23—H23C0.9600
C3—C41.393 (6)C24—H24A0.9600
C3—C111.495 (6)C24—H24B0.9600
C4—C51.386 (6)C24—H24C0.9600
C4—H40.9300C27—N9'1.311 (14)
C5—C61.475 (5)C27—N91.329 (10)
C6—C71.371 (6)N9—C281.222 (10)
C7—C81.390 (6)C28—N101.181 (8)
C7—H70.9300C29—C301.425 (9)
C8—C91.361 (7)C29—H29A0.9600
C8—C121.503 (7)C29—H29B0.9600
C9—C101.360 (6)C29—H29C0.9600
C9—H90.9300C30—O11.324 (8)
C10—H100.9300C30—H30A0.9700
C11—H11A0.9600C30—H30B0.9700
C11—H11B0.9600O1—H1A0.8200
C11—H11C0.9600
N8—Zn1—N594.05 (16)C8—C12—H12B109.5
N8—Zn1—N394.59 (14)H12A—C12—H12B109.5
N5—Zn1—N393.49 (14)C8—C12—H12C109.5
N8—Zn1—N293.40 (14)H12A—C12—H12C109.5
N5—Zn1—N294.37 (14)H12B—C12—H12C109.5
N3—Zn1—N2168.36 (13)N3—C13—C14123.0 (4)
N8—Zn1—N1168.71 (14)N3—C13—H13118.5
N5—Zn1—N189.18 (14)C14—C13—H13118.5
N3—Zn1—N196.01 (13)C13—C14—C15119.8 (4)
N2—Zn1—N175.55 (12)C13—C14—H14120.1
N8—Zn1—N493.27 (15)C15—C14—H14120.1
N5—Zn1—N4166.71 (14)C16—C15—C14116.8 (4)
N3—Zn1—N474.87 (13)C16—C15—C23121.0 (5)
N2—Zn1—N496.25 (13)C14—C15—C23122.2 (5)
N1—Zn1—N485.78 (13)C15—C16—C17121.1 (4)
C1—N1—C5118.5 (4)C15—C16—H16119.5
C1—N1—Zn1126.2 (3)C17—C16—H16119.5
C5—N1—Zn1115.2 (3)N3—C17—C16121.4 (4)
C6—N2—C10118.1 (4)N3—C17—C18116.1 (4)
C6—N2—Zn1116.7 (3)C16—C17—C18122.5 (4)
C10—N2—Zn1125.2 (3)N4—C18—C19121.9 (4)
C17—N3—C13117.9 (4)N4—C18—C17115.4 (3)
C17—N3—Zn1118.1 (3)C19—C18—C17122.8 (4)
C13—N3—Zn1123.9 (3)C18—C19—C20120.7 (4)
C22—N4—C18117.2 (4)C18—C19—H19119.6
C22—N4—Zn1127.5 (3)C20—C19—H19119.6
C18—N4—Zn1114.9 (3)C21—C20—C19116.9 (4)
C25—N5—Zn1172.1 (4)C21—C20—C24122.2 (5)
C26—N6—C25123.7 (5)C19—C20—C24120.9 (5)
C27—N8—Zn1171.7 (4)C20—C21—C22119.7 (4)
N1—C1—C2123.6 (4)C20—C21—H21120.2
N1—C1—H1118.2C22—C21—H21120.2
C2—C1—H1118.2N4—C22—C21123.6 (5)
C3—C2—C1119.2 (4)N4—C22—H22118.2
C3—C2—H2120.4C21—C22—H22118.2
C1—C2—H2120.4C15—C23—H23A109.5
C2—C3—C4117.5 (4)C15—C23—H23B109.5
C2—C3—C11121.7 (5)H23A—C23—H23B109.5
C4—C3—C11120.7 (5)C15—C23—H23C109.5
C5—C4—C3120.0 (4)H23A—C23—H23C109.5
C5—C4—H4120.0H23B—C23—H23C109.5
C3—C4—H4120.0C20—C24—H24A108.7
N1—C5—C4121.2 (4)C20—C24—H24B109.4
N1—C5—C6116.3 (4)H24A—C24—H24B109.5
C4—C5—C6122.5 (4)C20—C24—H24C110.2
N2—C6—C7120.5 (4)H24A—C24—H24C109.5
N2—C6—C5116.2 (4)H24B—C24—H24C109.5
C7—C6—C5123.3 (4)N5—C25—N6172.4 (5)
C6—C7—C8121.3 (4)N7—C26—N6173.0 (7)
C6—C7—H7119.3N8—C27—N9'160.3 (10)
C8—C7—H7119.3N8—C27—N9166.7 (8)
C9—C8—C7117.1 (4)C28—N9—C27119.0 (8)
C9—C8—C12122.4 (5)N10—C28—N9177.5 (10)
C7—C8—C12120.4 (5)C30—C29—H29A109.5
C10—C9—C8119.9 (4)C30—C29—H29B109.5
C10—C9—H9120.0H29A—C29—H29B109.5
C8—C9—H9120.0C30—C29—H29C109.5
N2—C10—C9123.0 (4)H29A—C29—H29C109.5
N2—C10—H10118.5H29B—C29—H29C109.5
C9—C10—H10118.5O1—C30—C29114.8 (9)
C3—C11—H11A109.5O1—C30—H30A108.6
C3—C11—H11B109.5C29—C30—H30A108.6
H11A—C11—H11B109.5O1—C30—H30B108.6
C3—C11—H11C109.5C29—C30—H30B108.6
H11A—C11—H11C109.5H30A—C30—H30B107.5
H11B—C11—H11C109.5C30—O1—H1A109.6
C8—C12—H12A109.5
N8—Zn1—N1—C1−167.9 (7)C3—C4—C5—N1−0.7 (7)
N5—Zn1—N1—C185.3 (4)C3—C4—C5—C6−179.3 (4)
N3—Zn1—N1—C1−8.1 (4)C10—N2—C6—C7−0.4 (6)
N2—Zn1—N1—C1−180.0 (4)Zn1—N2—C6—C7179.9 (3)
N4—Zn1—N1—C1−82.4 (4)C10—N2—C6—C5179.6 (4)
N8—Zn1—N1—C513.2 (9)Zn1—N2—C6—C5−0.1 (5)
N5—Zn1—N1—C5−93.6 (3)N1—C5—C6—N21.1 (5)
N3—Zn1—N1—C5173.0 (3)C4—C5—C6—N2179.8 (4)
N2—Zn1—N1—C51.1 (3)N1—C5—C6—C7−178.9 (4)
N4—Zn1—N1—C598.7 (3)C4—C5—C6—C7−0.2 (7)
N8—Zn1—N2—C6−178.2 (3)N2—C6—C7—C8−0.6 (7)
N5—Zn1—N2—C687.5 (3)C5—C6—C7—C8179.4 (4)
N3—Zn1—N2—C6−44.8 (8)C6—C7—C8—C91.8 (7)
N1—Zn1—N2—C6−0.5 (3)C6—C7—C8—C12−177.2 (5)
N4—Zn1—N2—C6−84.5 (3)C7—C8—C9—C10−2.1 (7)
N8—Zn1—N2—C102.1 (4)C12—C8—C9—C10177.0 (5)
N5—Zn1—N2—C10−92.2 (4)C6—N2—C10—C90.1 (7)
N3—Zn1—N2—C10135.5 (6)Zn1—N2—C10—C9179.8 (3)
N1—Zn1—N2—C10179.8 (4)C8—C9—C10—N21.2 (7)
N4—Zn1—N2—C1095.8 (4)C17—N3—C13—C141.6 (6)
N8—Zn1—N3—C1799.3 (3)Zn1—N3—C13—C14−174.2 (3)
N5—Zn1—N3—C17−166.3 (3)N3—C13—C14—C150.6 (7)
N2—Zn1—N3—C17−33.9 (8)C13—C14—C15—C16−2.5 (7)
N1—Zn1—N3—C17−76.8 (3)C13—C14—C15—C23175.8 (5)
N4—Zn1—N3—C177.2 (3)C14—C15—C16—C172.4 (7)
N8—Zn1—N3—C13−85.0 (3)C23—C15—C16—C17−175.9 (5)
N5—Zn1—N3—C139.4 (3)C13—N3—C17—C16−1.7 (6)
N2—Zn1—N3—C13141.8 (6)Zn1—N3—C17—C16174.3 (3)
N1—Zn1—N3—C1398.9 (3)C13—N3—C17—C18177.7 (3)
N4—Zn1—N3—C13−177.1 (3)Zn1—N3—C17—C18−6.3 (4)
N8—Zn1—N4—C2285.9 (4)C15—C16—C17—N3−0.4 (7)
N5—Zn1—N4—C22−150.8 (6)C15—C16—C17—C18−179.7 (4)
N3—Zn1—N4—C22179.7 (4)C22—N4—C18—C19−0.3 (6)
N2—Zn1—N4—C22−7.9 (4)Zn1—N4—C18—C19−174.1 (3)
N1—Zn1—N4—C22−82.9 (4)C22—N4—C18—C17−179.9 (4)
N8—Zn1—N4—C18−101.0 (3)Zn1—N4—C18—C176.3 (4)
N5—Zn1—N4—C1822.3 (8)N3—C17—C18—N4−0.3 (5)
N3—Zn1—N4—C18−7.1 (3)C16—C17—C18—N4179.1 (4)
N2—Zn1—N4—C18165.2 (3)N3—C17—C18—C19−179.8 (4)
N1—Zn1—N4—C1890.3 (3)C16—C17—C18—C19−0.5 (6)
C5—N1—C1—C2−0.1 (7)N4—C18—C19—C200.7 (6)
Zn1—N1—C1—C2−179.0 (3)C17—C18—C19—C20−179.8 (4)
N1—C1—C2—C3−0.7 (8)C18—C19—C20—C21−0.5 (7)
C1—C2—C3—C40.8 (7)C18—C19—C20—C24177.3 (4)
C1—C2—C3—C11−179.2 (5)C19—C20—C21—C220.0 (8)
C2—C3—C4—C5−0.1 (7)C24—C20—C21—C22−177.7 (5)
C11—C3—C4—C5179.8 (5)C18—N4—C22—C21−0.2 (7)
C1—N1—C5—C40.8 (6)Zn1—N4—C22—C21172.8 (4)
Zn1—N1—C5—C4179.8 (3)C20—C21—C22—N40.4 (8)
C1—N1—C5—C6179.5 (4)N8—C27—N9—C28−134 (3)
Zn1—N1—C5—C6−1.5 (5)N9'—C27—N9—C2872.4 (17)
Acknowledgements top

The authors acknowledge the kind help of Dr Hai-Bin Song, financial support from the National Natural Science Foundation of China (Nos. 20675041), Tianjin University for Young Teachers, and instrument support from Tianjin University Experiment Centre.

references
References top

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