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Acta Cryst. (2007). E63, m3022    [ doi:10.1107/S1600536807058023 ]

(4-Hydroxycinnamato)[tris(N-methylbenzimidazol-2-ylmethyl)amine]zinc(II)] perchlorate-dimethylformamide-ethanol-methanol (2/2/2/1)

H. Wu, R. Yun, J. Ding and J. Yuan

Abstract top

In the title complex, [Zn(C9H7O3)(C27H27N7)]ClO4·C3H7NO·C2H6O·0.5CH4O, the ZnII ion is five-coordinated by four N atoms from a tris(N-methylbenzimidazol-2-ylmethyl)amine ligand and one O atom from a 4-hydroxycinnamate ligand in a distorted trigonal-bipyramidal geometry. The atoms of the ethanol and methanol solvent molecules are disordered over two sites with equal occupancy.

Comment top

The asymmetric unit of the title compound (Fig. 1) consists of a [Zn(Mentb)(4-hydroxycinnamate)] cation, a perchlorate anion, one molecule of DMF and ethanol, and a hemimethanol molecule. The zinc ion is five-coordinate with a N4O ligand set. The Mentb ligand acts as a tetradentate N-donor, and an O atom of carboxylate groups of the 4-hydroxycinnamate completes the coordination. The coordination geometry of the ZnII may be best described as distorted trigonal bipyramid (τ = 0.86). The parameter τ is defined as (β - α)/60 [where β = O1—Zn—N7, α = O1—Zn—N1] and its value varies from 0 (in regular square-based pyramidal) to 1 (in regular trigonal bipyramidal) (Youngme et al., 2007). The equatorial plane is occupied by three N atoms of three benzimidazolyl groups, while the ZnII atom protrudes towards O1 and is 0.561Å from the plane of atoms N1, N3 and N5. The axial positions are occupyied by N7 and O1, with Zn—N7 2.453 (2) Å, Zn—O1 1.974 (2)Å and O1—Zn—N7 167.13 (8)°. The three benzimidazole ring arms of the Mentb ligand form a cone-shaped cavity. The angles N3—Zn—N1, N5—Zn—N1 and N5—Zn—N3 are 110.28 (9), 114.28 (8) and 113.99 (9)°, respectively. The N7—Zn—N1 74.74 (9), N7—Zn—N3 74.15 (8) and N7—Zn—N5, 73.65 (8)° angles, which are all less than 90°. The distance between ZnII and O2 is 3.063 (2) Å, so O2 is not coordinated. The angles and distance in the Mentb and 4-hydroxycinnamate are normal (Allen et al., 1987). The rystal packing is stabilized by O—H···O hydrogen-bonding interactions (Fig. 2).

Related literature top

For related literature, see: Allen et al. (1987); Youngme et al. (2007).

Experimental top

To a stirred solution of tris(N-methylbenzimidazol-2-ylmethyl)amine (0.0899 g, 0.2 mmol) in hot MeOH (10 ml) was added Zn(ClO4)2 (H2O)6 (0.0745 g, 0.2 mmol), followed by a solution of Na(4-hydroxycinnamate) (0.0372 g, 0.2 mmol) in MeOH (5 ml). A colorless crystalline product formed rapidly. The precipitate was filtered off, washed with MeOH,EtOH and absolute Et2O, and dried in vacuo. The dried precipitate was dissolved in DMF to a colorless solution that was allowed to evaporate at room temperature. colorless crystals suitable for X-ray diffraction studies were obtained after two weeks. Yield, 0.135 g (74%). (found: C, 54.37; H, 5.22; N,12.36. Calcd. for C41.50H49ClN8O9.50Zn: C, 54.61; H, 5.41; N, 12.28)

Refinement top

The atoms of the ethanol and methanol solvate are disordered of two sites with equal occupancy. All H atoms were geometrically positioned and refined using a riding-model with C—H distances ranging from 0.95 to 0.99 Å and O—H = 0.84Å and Uiso(H) = 1.2 Ueq(C) or Uiso(H) = 1.5 Ueq(Cmethyl,O).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top
[Figure 1] Fig. 1. Crystal structure and atom numbering of the title compound.
[Figure 2] Fig. 2. The Packing diagram of the title compound. H bonds shown as dashed lines.
(4-Hydroxycinnamato)[tris(N-methylbenzimidazol-2-ylmethyl)amine]zinc(II)] perchlorate–dimethylformamide–ethanol–methanol (2/2/2/1) top
Crystal data top
[Zn(C9H7O3)(C27H27N7)]ClO4·C3H7NO·C2H6O·0.5CH4OF000 = 3816
Mr = 912.71Dx = 1.346 Mg m−3
Monoclinic, C2/cMo Kα radiation
λ = 0.71073 Å
a = 32.0342 (8) ÅCell parameters from 32283 reflections
b = 15.5594 (5) Åθ = 3.0–27.5º
c = 22.1536 (5) ŵ = 0.67 mm−1
β = 125.338 (10)ºT = 153 (2) K
V = 9007.6 (4) Å3Block, colorless
Z = 80.58 × 0.53 × 0.38 mm
Data collection top
Rigaku R-axis Spider
diffractometer		8367 independent reflections
Radiation source: Rotating Anode7232 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.026
T = 153(2) Kθmax = 25.5º
ω scansθmin = 3.1º
Absorption correction: multi-scan
(Higashi; 1995)		h = −38→38
Tmin = 0.698, Tmax = 0.786k = −18→18
36372 measured reflectionsl = −26→26
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)] = 0.046H-atom parameters constrained
wR(F2) = 0.155  w = 1/[σ2(Fo2) + (0.1005P)2 + 14.7697P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.002
8367 reflectionsΔρmax = 1.20 e Å−3
582 parametersΔρmin = −0.53 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Zn(C9H7O3)(C27H27N7)]ClO4·C3H7NO·C2H6O·0.5CH4OV = 9007.6 (4) Å3
Mr = 912.71Z = 8
Monoclinic, C2/cMo Kα
a = 32.0342 (8) ŵ = 0.67 mm−1
b = 15.5594 (5) ÅT = 153 (2) K
c = 22.1536 (5) Å0.58 × 0.53 × 0.38 mm
β = 125.338 (10)º
Data collection top
Rigaku R-axis Spider
diffractometer		8367 independent reflections
Absorption correction: multi-scan
(Higashi; 1995)		7232 reflections with I > 2σ(I)
Tmin = 0.698, Tmax = 0.786Rint = 0.026
36372 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.155  w = 1/[σ2(Fo2) + (0.1005P)2 + 14.7697P]
where P = (Fo2 + 2Fc2)/3
S = 1.04Δρmax = 1.20 e Å−3
8367 reflectionsΔρmin = −0.53 e Å−3
582 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 > 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*/UeqOcc. (<1)
Zn0.078081 (11)0.750336 (17)0.059720 (15)0.02571 (12)
Cl0.09422 (3)0.26335 (5)0.27601 (4)0.03521 (18)
O10.08765 (8)0.71180 (13)0.15189 (11)0.0406 (5)
O20.08059 (11)0.84273 (15)0.18386 (13)0.0596 (7)
O30.17586 (9)0.50549 (16)0.56220 (11)0.0470 (5)
H30.19290.46050.57060.056*
O40.14662 (10)0.2631 (2)0.33752 (16)0.0781 (10)
O50.06623 (10)0.20352 (16)0.28876 (13)0.0544 (6)
O60.07260 (12)0.34759 (16)0.26806 (15)0.0659 (7)
O70.08874 (10)0.24106 (15)0.20881 (13)0.0499 (6)
O80.22487 (11)0.35802 (17)0.58986 (15)0.0632 (7)
O90.0375 (3)0.8967 (4)0.2674 (4)0.0854 (19)0.50
H90.04190.89630.23360.128*0.50
O10−0.19155 (11)0.9252 (2)0.03371 (18)0.0792 (9)
H10−0.16360.90600.04430.095*
N10.01650 (8)0.82827 (15)−0.00654 (12)0.0326 (5)
N2−0.02600 (10)0.92314 (16)−0.09803 (14)0.0463 (7)
N30.14463 (8)0.81120 (14)0.08906 (11)0.0284 (5)
N40.20541 (9)0.83904 (16)0.07238 (14)0.0367 (5)
N50.07008 (8)0.62744 (14)0.01897 (11)0.0268 (4)
N60.04009 (8)0.53490 (14)−0.07408 (12)0.0297 (5)
N70.07240 (9)0.76521 (14)−0.05503 (12)0.0298 (5)
N80.25900 (11)0.34541 (19)0.71284 (16)0.0521 (7)
C10.04634 (11)0.84674 (18)−0.08750 (15)0.0369 (6)
H1A0.02600.8434−0.14210.044*
H1B0.07180.8934−0.07080.044*
C20.01215 (10)0.86516 (17)−0.06387 (14)0.0350 (6)
C3−0.04099 (17)0.9714 (2)−0.16462 (19)0.0703 (13)
H3A−0.01040.9946−0.15860.084*
H3B−0.06371.0187−0.17210.084*
H3C−0.05890.9331−0.20760.084*
C4−0.04866 (11)0.9244 (2)−0.06052 (18)0.0477 (8)
C5−0.08978 (14)0.9717 (2)−0.0720 (2)0.0691 (13)
H5−0.10701.0132−0.11040.083*
C6−0.10405 (13)0.9561 (3)−0.0264 (3)0.0762 (15)
H6−0.13190.9872−0.03300.091*
C7−0.07855 (14)0.8949 (3)0.0305 (3)0.0685 (13)
H7−0.08990.88520.06120.082*
C8−0.03720 (12)0.8481 (2)0.0431 (2)0.0489 (8)
H8−0.01990.80710.08190.059*
C9−0.02249 (10)0.86409 (19)−0.00359 (17)0.0397 (7)
C100.12566 (11)0.76483 (19)−0.03122 (16)0.0346 (6)
H10A0.12860.7967−0.06730.042*
H10B0.13720.7050−0.02840.042*
C110.15818 (10)0.80646 (17)0.04318 (14)0.0309 (5)
C120.23281 (13)0.8447 (2)0.0380 (2)0.0516 (8)
H12A0.21340.8145−0.00960.062*
H12B0.26660.81810.07050.062*
H12C0.23680.90520.02990.062*
C130.22484 (11)0.86450 (18)0.14409 (16)0.0378 (6)
C140.27295 (12)0.8962 (2)0.2012 (2)0.0519 (8)
H140.29930.90580.19450.062*
C150.27985 (13)0.9126 (2)0.26715 (19)0.0562 (9)
H150.31210.93330.30750.067*
C160.24137 (13)0.9001 (2)0.27703 (18)0.0531 (8)
H160.24760.91390.32340.064*
C170.19373 (12)0.8677 (2)0.22069 (16)0.0411 (7)
H170.16740.85920.22750.049*
C180.18653 (10)0.84843 (17)0.15427 (15)0.0326 (6)
C190.04282 (10)0.69104 (17)−0.10112 (14)0.0317 (6)
H19A0.05370.6753−0.13340.038*
H19B0.00590.7055−0.13290.038*
C200.05185 (9)0.61738 (16)−0.05163 (14)0.0275 (5)
C210.01773 (11)0.50181 (19)−0.14887 (15)0.0386 (6)
H21A0.00700.5500−0.18330.046*
H21B−0.01210.4660−0.16420.046*
H21C0.04320.4673−0.14900.046*
C220.05093 (9)0.48669 (17)−0.01402 (14)0.0299 (5)
C230.04592 (10)0.39947 (18)−0.00567 (17)0.0378 (6)
H230.03240.3605−0.04590.045*
C240.06148 (11)0.37225 (19)0.06356 (17)0.0388 (6)
H240.05930.31290.07150.047*
C250.08045 (10)0.42973 (19)0.12242 (16)0.0371 (6)
H250.09040.40860.16920.044*
C260.08518 (10)0.51715 (18)0.11426 (15)0.0325 (6)
H260.09820.55600.15450.039*
C270.07000 (9)0.54537 (17)0.04436 (14)0.0281 (5)
C280.08855 (12)0.76500 (19)0.19611 (17)0.0377 (6)
C290.10197 (13)0.7321 (2)0.26800 (18)0.0443 (7)
H290.10190.77160.30060.053*
C300.11405 (12)0.6513 (2)0.28966 (16)0.0410 (7)
H300.11300.61290.25550.049*
C310.12889 (11)0.6139 (2)0.36029 (16)0.0392 (6)
C320.14191 (12)0.5278 (2)0.37396 (17)0.0418 (7)
H320.13960.49380.33660.050*
C330.15824 (11)0.4897 (2)0.44118 (16)0.0405 (7)
H330.16770.43070.44970.049*
C340.16062 (11)0.5385 (2)0.49557 (15)0.0380 (6)
C350.14651 (12)0.6246 (2)0.48222 (16)0.0422 (7)
H350.14770.65800.51900.051*
C360.13084 (12)0.6615 (2)0.41574 (17)0.0424 (7)
H360.12120.72040.40720.051*
C370.30445 (16)0.3253 (3)0.7867 (2)0.0781 (13)
H37A0.33330.31340.78370.094*
H37B0.29770.27470.80610.094*
H37C0.31280.37440.81960.094*
C380.21247 (14)0.3648 (2)0.7068 (2)0.0561 (9)
H38A0.18430.37300.65460.067*
H38B0.21730.41740.73440.067*
H38C0.20430.31700.72720.067*
C390.26060 (14)0.3424 (2)0.6547 (2)0.0560 (9)
H390.29230.32660.66340.067*
C400.00000.8452 (6)0.25000.097 (2)
H40A−0.01100.85690.28230.150*0.50
H40B0.01170.78560.25660.150*0.50
H40C−0.02870.85460.19830.150*0.50
C41−0.1478 (3)1.0074 (5)0.1414 (4)0.063 (2)0.50
H41A−0.11410.97990.16840.076*0.50
H41B−0.15321.03330.17670.076*0.50
H41C−0.14951.05220.10890.076*0.50
C42−0.18727 (19)0.9434 (4)0.0970 (3)0.0335 (12)0.50
H42A−0.17890.89010.12640.040*0.50
H42B−0.22050.96510.08440.040*0.50
C41'−0.2317 (3)0.8500 (5)−0.0807 (4)0.0530 (18)0.50
H41D−0.24210.9042−0.10820.064*0.50
H41E−0.25740.8057−0.11070.064*0.50
H41F−0.19850.8321−0.06930.064*0.50
C42'−0.22735 (18)0.8618 (3)−0.0117 (3)0.0302 (11)0.50
H42C−0.26120.8779−0.02360.036*0.50
H42D−0.21710.80660.01550.036*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.02397 (19)0.02513 (19)0.02573 (19)−0.00064 (10)0.01306 (15)−0.00058 (10)
Cl0.0322 (4)0.0421 (4)0.0278 (3)−0.0025 (3)0.0153 (3)−0.0015 (3)
O10.0539 (12)0.0346 (11)0.0384 (11)0.0028 (9)0.0296 (10)0.0020 (9)
O20.0795 (17)0.0370 (13)0.0493 (13)0.0159 (12)0.0297 (13)0.0025 (10)
O30.0449 (12)0.0595 (15)0.0357 (11)−0.0006 (10)0.0227 (10)0.0042 (10)
O40.0324 (13)0.143 (3)0.0455 (15)−0.0061 (14)0.0147 (12)−0.0068 (15)
O50.0643 (15)0.0533 (15)0.0580 (14)−0.0133 (12)0.0425 (12)−0.0063 (11)
O60.097 (2)0.0418 (14)0.0601 (16)0.0092 (13)0.0463 (15)−0.0019 (11)
O70.0620 (15)0.0550 (15)0.0397 (13)0.0018 (11)0.0334 (12)−0.0026 (9)
O80.0632 (16)0.0553 (16)0.0582 (16)0.0020 (13)0.0276 (14)−0.0032 (12)
O90.117 (5)0.066 (4)0.118 (5)−0.008 (4)0.094 (5)−0.009 (4)
O100.0611 (17)0.089 (2)0.096 (2)−0.0030 (16)0.0507 (17)−0.0127 (17)
N10.0275 (11)0.0283 (12)0.0342 (12)0.0002 (9)0.0133 (9)−0.0037 (9)
N20.0421 (14)0.0289 (13)0.0353 (13)0.0103 (11)0.0036 (11)−0.0054 (10)
N30.0260 (10)0.0274 (11)0.0258 (11)−0.0033 (9)0.0115 (9)−0.0019 (8)
N40.0298 (12)0.0365 (13)0.0456 (14)−0.0049 (10)0.0227 (11)−0.0034 (10)
N50.0242 (10)0.0266 (11)0.0277 (11)−0.0011 (8)0.0138 (9)−0.0001 (8)
N60.0265 (11)0.0279 (11)0.0314 (11)−0.0013 (9)0.0149 (9)−0.0043 (9)
N70.0281 (11)0.0292 (11)0.0265 (11)−0.0023 (9)0.0126 (9)−0.0009 (8)
N80.0413 (15)0.0469 (16)0.0565 (17)−0.0029 (12)0.0217 (13)−0.0056 (13)
C10.0424 (16)0.0288 (14)0.0314 (14)−0.0004 (12)0.0168 (12)0.0032 (11)
C20.0318 (14)0.0232 (13)0.0304 (14)0.0003 (11)0.0066 (11)−0.0038 (10)
C30.085 (3)0.0337 (18)0.0385 (18)0.0203 (18)0.0048 (18)0.0020 (14)
C40.0305 (14)0.0344 (16)0.0473 (18)0.0033 (12)0.0047 (13)−0.0187 (13)
C50.0387 (18)0.047 (2)0.073 (3)0.0137 (16)0.0042 (18)−0.0307 (18)
C60.0307 (17)0.065 (3)0.097 (3)0.0073 (17)0.017 (2)−0.049 (2)
C70.045 (2)0.062 (2)0.106 (3)−0.0182 (19)0.048 (2)−0.050 (2)
C80.0380 (16)0.0386 (17)0.072 (2)−0.0078 (13)0.0332 (16)−0.0209 (15)
C90.0237 (13)0.0309 (15)0.0496 (17)−0.0008 (11)0.0125 (12)−0.0175 (12)
C100.0344 (15)0.0385 (15)0.0344 (15)−0.0066 (12)0.0219 (13)−0.0046 (11)
C110.0264 (12)0.0287 (13)0.0343 (14)−0.0010 (10)0.0157 (11)−0.0003 (10)
C120.0405 (17)0.062 (2)0.064 (2)−0.0087 (15)0.0372 (16)−0.0047 (16)
C130.0294 (14)0.0309 (14)0.0418 (16)−0.0038 (11)0.0141 (12)−0.0035 (12)
C140.0300 (15)0.049 (2)0.062 (2)−0.0117 (14)0.0186 (15)−0.0070 (16)
C150.0369 (17)0.054 (2)0.0478 (19)−0.0147 (15)0.0070 (14)−0.0144 (15)
C160.0488 (19)0.051 (2)0.0386 (17)−0.0127 (15)0.0131 (14)−0.0116 (14)
C170.0398 (16)0.0385 (16)0.0345 (15)−0.0076 (13)0.0155 (13)−0.0071 (12)
C180.0266 (13)0.0260 (13)0.0340 (14)−0.0036 (10)0.0110 (11)−0.0023 (10)
C190.0322 (13)0.0309 (14)0.0273 (13)−0.0048 (11)0.0145 (11)−0.0028 (10)
C200.0206 (11)0.0282 (13)0.0321 (13)−0.0014 (10)0.0144 (10)−0.0027 (10)
C210.0391 (15)0.0366 (16)0.0340 (15)−0.0045 (12)0.0177 (12)−0.0112 (12)
C220.0213 (12)0.0307 (14)0.0357 (14)−0.0012 (10)0.0154 (10)−0.0014 (10)
C230.0300 (14)0.0287 (14)0.0503 (17)−0.0034 (11)0.0208 (13)−0.0046 (12)
C240.0331 (14)0.0276 (14)0.0550 (18)−0.0002 (11)0.0251 (13)0.0057 (12)
C250.0324 (14)0.0346 (15)0.0441 (16)0.0035 (12)0.0220 (12)0.0095 (12)
C260.0272 (13)0.0322 (14)0.0371 (14)0.0016 (11)0.0180 (11)0.0025 (11)
C270.0204 (11)0.0268 (13)0.0343 (13)0.0000 (10)0.0142 (10)0.0017 (10)
C280.0375 (16)0.0370 (16)0.0394 (16)0.0037 (12)0.0227 (13)−0.0004 (12)
C290.0499 (18)0.0475 (18)0.0404 (17)0.0026 (14)0.0290 (15)−0.0028 (13)
C300.0473 (17)0.0427 (17)0.0394 (16)−0.0042 (13)0.0288 (14)−0.0061 (12)
C310.0408 (15)0.0434 (17)0.0385 (15)−0.0075 (13)0.0258 (13)−0.0043 (12)
C320.0463 (17)0.0444 (17)0.0403 (16)−0.0071 (13)0.0283 (14)−0.0057 (13)
C330.0405 (15)0.0425 (17)0.0427 (16)−0.0062 (13)0.0265 (13)−0.0002 (13)
C340.0311 (14)0.0500 (18)0.0331 (15)−0.0073 (12)0.0187 (12)−0.0005 (12)
C350.0434 (16)0.0506 (18)0.0377 (16)−0.0070 (14)0.0265 (13)−0.0069 (13)
C360.0441 (16)0.0423 (17)0.0445 (17)−0.0028 (13)0.0278 (14)−0.0037 (13)
C370.055 (2)0.100 (4)0.061 (2)0.003 (2)0.023 (2)−0.006 (2)
C380.054 (2)0.0449 (19)0.068 (2)−0.0019 (16)0.0347 (18)−0.0066 (16)
C390.050 (2)0.050 (2)0.066 (2)−0.0037 (16)0.0325 (19)−0.0086 (17)
C400.094 (5)0.111 (6)0.125 (6)0.0000.086 (5)0.000
C410.042 (4)0.078 (5)0.033 (3)0.011 (3)0.000 (3)−0.023 (3)
C420.025 (2)0.046 (3)0.018 (2)0.016 (2)0.006 (2)0.008 (2)
C41'0.040 (3)0.076 (5)0.051 (4)−0.020 (3)0.031 (3)−0.033 (3)
C42'0.015 (2)0.032 (3)0.041 (3)0.0020 (19)0.014 (2)−0.007 (2)
Geometric parameters (Å, °) top
Zn—O11.9745 (19)C13—C141.401 (4)
Zn—N12.041 (2)C14—C151.370 (5)
Zn—N32.064 (2)C14—H140.9500
Zn—N52.066 (2)C15—C161.385 (5)
Zn—N72.452 (2)C15—H150.9500
Cl—O41.424 (3)C16—C171.392 (4)
Cl—O51.429 (2)C16—H160.9500
Cl—O71.437 (2)C17—C181.384 (4)
Cl—O61.445 (3)C17—H170.9500
O1—C281.270 (4)C19—C201.494 (4)
O2—C281.233 (4)C19—H19A0.9900
O3—C341.359 (3)C19—H19B0.9900
O3—H30.8400C21—H21A0.9800
O8—C391.237 (4)C21—H21B0.9800
O9—C401.302 (8)C21—H21C0.9800
O9—H90.8400C22—C231.391 (4)
O10—C421.358 (6)C22—C271.402 (4)
O10—C42'1.402 (6)C23—C241.377 (4)
O10—H100.8400C23—H230.9500
N1—C21.325 (4)C24—C251.397 (4)
N1—C91.403 (4)C24—H240.9500
N2—C21.345 (4)C25—C261.392 (4)
N2—C41.384 (5)C25—H250.9500
N2—C31.467 (5)C26—C271.398 (4)
N3—C111.318 (3)C26—H260.9500
N3—C181.407 (3)C28—C291.480 (4)
N4—C111.354 (3)C29—C301.321 (5)
N4—C131.387 (4)C29—H290.9500
N4—C121.461 (4)C30—C311.467 (4)
N5—C201.325 (3)C30—H300.9500
N5—C271.396 (3)C31—C321.384 (5)
N6—C201.349 (3)C31—C361.404 (4)
N6—C221.385 (3)C32—C331.394 (4)
N6—C211.466 (3)C32—H320.9500
N7—C11.459 (4)C33—C341.389 (4)
N7—C101.466 (4)C33—H330.9500
N7—C191.467 (3)C34—C351.389 (5)
N8—C391.320 (5)C35—C361.378 (4)
N8—C381.449 (5)C35—H350.9500
N8—C371.462 (5)C36—H360.9500
C1—C21.490 (4)C37—H37A0.9800
C1—H1A0.9900C37—H37B0.9800
C1—H1B0.9900C37—H37C0.9800
C3—H3A0.9800C38—H38A0.9800
C3—H3B0.9800C38—H38B0.9800
C3—H3C0.9800C38—H38C0.9800
C4—C91.397 (5)C39—H390.9500
C4—C51.398 (5)C40—O9i1.302 (8)
C5—C61.350 (7)C40—H40A0.9801
C5—H50.9500C40—H40B0.9801
C6—C71.404 (7)C40—H40C0.9801
C6—H60.9500C41—C421.456 (9)
C7—C81.391 (5)C41—H41A0.9800
C7—H70.9500C41—H41B0.9800
C8—C91.385 (5)C41—H41C0.9800
C8—H80.9500C42—H42A0.9900
C10—C111.495 (4)C42—H42B0.9900
C10—H10A0.9900C41'—C42'1.462 (8)
C10—H10B0.9900C41'—H41D0.9800
C12—H12A0.9800C41'—H41E0.9800
C12—H12B0.9800C41'—H41F0.9800
C12—H12C0.9800C42'—H42C0.9900
C13—C181.393 (4)C42'—H42D0.9900
O1—Zn—N1115.56 (9)C13—C14—H14121.9
O1—Zn—N3107.42 (9)C14—C15—C16122.2 (3)
N1—Zn—N3110.27 (9)C14—C15—H15118.9
O1—Zn—N594.39 (8)C16—C15—H15118.9
N1—Zn—N5114.30 (8)C15—C16—C17121.6 (3)
N3—Zn—N5114.00 (8)C15—C16—H16119.2
O1—Zn—N7167.08 (8)C17—C16—H16119.2
N1—Zn—N774.75 (9)C18—C17—C16117.0 (3)
N3—Zn—N774.16 (8)C18—C17—H17121.5
N5—Zn—N773.64 (8)C16—C17—H17121.5
O4—Cl—O5109.65 (18)C17—C18—C13120.8 (3)
O4—Cl—O7111.16 (17)C17—C18—N3130.8 (3)
O5—Cl—O7109.44 (14)C13—C18—N3108.3 (2)
O4—Cl—O6109.59 (19)N7—C19—C20108.6 (2)
O5—Cl—O6107.67 (16)N7—C19—H19A110.0
O7—Cl—O6109.26 (15)C20—C19—H19A110.0
C28—O1—Zn121.4 (2)N7—C19—H19B110.0
C34—O3—H3109.5C20—C19—H19B110.0
C40—O9—H9109.5H19A—C19—H19B108.3
O9—C40—H40A109.4N5—C20—N6112.7 (2)
O9—C40—H40B109.5N5—C20—C19122.8 (2)
H40A—C40—H40B109.5N6—C20—C19124.4 (2)
O9—C40—H40C109.6N6—C21—H21A109.5
H40A—C40—H40C109.5N6—C21—H21B109.5
H40B—C40—H40C109.5H21A—C21—H21B109.5
C42—O10—C42'116.2 (4)N6—C21—H21C109.5
C42—O10—H10109.5H21A—C21—H21C109.5
C42'—O10—H10104.3H21B—C21—H21C109.5
C2—N1—C9105.6 (2)N6—C22—C23132.2 (2)
C2—N1—Zn117.95 (19)N6—C22—C27105.5 (2)
C9—N1—Zn135.9 (2)C23—C22—C27122.3 (3)
C2—N2—C4107.0 (3)C24—C23—C22116.9 (3)
C2—N2—C3124.8 (3)C24—C23—H23121.5
C4—N2—C3128.1 (3)C22—C23—H23121.5
C11—N3—C18105.7 (2)C23—C24—C25121.6 (3)
C11—N3—Zn118.18 (17)C23—C24—H24119.2
C18—N3—Zn135.24 (18)C25—C24—H24119.2
C11—N4—C13106.9 (2)C26—C25—C24121.7 (3)
C11—N4—C12128.0 (3)C26—C25—H25119.1
C13—N4—C12125.0 (3)C24—C25—H25119.1
C20—N5—C27105.4 (2)C25—C26—C27117.2 (3)
C20—N5—Zn118.93 (17)C25—C26—H26121.4
C27—N5—Zn134.36 (17)C27—C26—H26121.4
C20—N6—C22107.4 (2)N5—C27—C26130.8 (2)
C20—N6—C21126.9 (2)N5—C27—C22109.0 (2)
C22—N6—C21125.6 (2)C26—C27—C22120.3 (2)
C1—N7—C10113.3 (2)O2—C28—O1124.0 (3)
C1—N7—C19112.7 (2)O2—C28—C29118.0 (3)
C10—N7—C19113.3 (2)O1—C28—C29117.9 (3)
C1—N7—Zn105.75 (17)C30—C29—C28124.1 (3)
C10—N7—Zn104.69 (16)C30—C29—H29117.9
C19—N7—Zn106.14 (16)C28—C29—H29117.9
C39—N8—C38122.4 (3)C29—C30—C31127.6 (3)
C39—N8—C37120.6 (3)C29—C30—H30116.2
C38—N8—C37117.0 (3)C31—C30—H30116.2
N7—C1—C2108.7 (2)C32—C31—C36117.6 (3)
N7—C1—H1A109.9C32—C31—C30119.2 (3)
C2—C1—H1A109.9C36—C31—C30123.1 (3)
N7—C1—H1B109.9C31—C32—C33121.7 (3)
C2—C1—H1B109.9C31—C32—H32119.2
H1A—C1—H1B108.3C33—C32—H32119.2
N1—C2—N2112.8 (3)C34—C33—C32119.5 (3)
N1—C2—C1124.2 (2)C34—C33—H33120.2
N2—C2—C1123.0 (3)C32—C33—H33120.2
N2—C3—H3A109.5O3—C34—C33122.7 (3)
N2—C3—H3B109.5O3—C34—C35117.6 (3)
H3A—C3—H3B109.5C33—C34—C35119.6 (3)
N2—C3—H3C109.5C36—C35—C34120.2 (3)
H3A—C3—H3C109.5C36—C35—H35119.9
H3B—C3—H3C109.5C34—C35—H35119.9
N2—C4—C9106.5 (3)C35—C36—C31121.3 (3)
N2—C4—C5131.6 (4)C35—C36—H36119.4
C9—C4—C5121.9 (4)C31—C36—H36119.4
C6—C5—C4117.4 (4)N8—C37—H37A109.5
C6—C5—H5121.3N8—C37—H37B109.5
C4—C5—H5121.3H37A—C37—H37B109.5
C5—C6—C7121.4 (3)N8—C37—H37C109.5
C5—C6—H6119.3H37A—C37—H37C109.5
C7—C6—H6119.3H37B—C37—H37C109.5
C8—C7—C6121.9 (4)N8—C38—H38A109.5
C8—C7—H7119.1N8—C38—H38B109.5
C6—C7—H7119.1H38A—C38—H38B109.5
C9—C8—C7116.8 (4)N8—C38—H38C109.5
C9—C8—H8121.6H38A—C38—H38C109.5
C7—C8—H8121.6H38B—C38—H38C109.5
C8—C9—C4120.6 (3)O8—C39—N8126.4 (4)
C8—C9—N1131.3 (3)O8—C39—H39116.8
C4—C9—N1108.1 (3)N8—C39—H39116.8
N7—C10—C11108.6 (2)O9—C40—O9i104.1 (9)
N7—C10—H10A110.0O10—C42—C41111.7 (5)
C11—C10—H10A110.0O10—C42—H42A109.3
N7—C10—H10B110.0C41—C42—H42A109.3
C11—C10—H10B110.0O10—C42—H42B109.3
H10A—C10—H10B108.4C41—C42—H42B109.3
N3—C11—N4112.7 (2)H42A—C42—H42B107.9
N3—C11—C10123.0 (2)C42'—C41'—H41D109.5
N4—C11—C10124.2 (2)C42'—C41'—H41E109.5
N4—C12—H12A109.5H41D—C41'—H41E109.5
N4—C12—H12B109.5C42'—C41'—H41F109.5
H12A—C12—H12B109.5H41D—C41'—H41F109.5
N4—C12—H12C109.5H41E—C41'—H41F109.5
H12A—C12—H12C109.5O10—C42'—C41'112.5 (5)
H12B—C12—H12C109.5O10—C42'—H42C109.1
N4—C13—C18106.3 (2)C41'—C42'—H42C109.1
N4—C13—C14131.7 (3)O10—C42'—H42D109.1
C18—C13—C14122.0 (3)C41'—C42'—H42D109.1
C15—C14—C13116.3 (3)H42C—C42'—H42D107.8
C15—C14—H14121.9
N1—Zn—O1—C28−51.9 (3)C13—N4—C11—N32.1 (3)
N3—Zn—O1—C2871.7 (2)C12—N4—C11—N3−180.0 (3)
N5—Zn—O1—C28−171.5 (2)C13—N4—C11—C10−174.6 (3)
N7—Zn—O1—C28166.7 (3)C12—N4—C11—C103.4 (5)
O1—Zn—N1—C2171.17 (18)N7—C10—C11—N323.3 (4)
N3—Zn—N1—C249.1 (2)N7—C10—C11—N4−160.3 (3)
N5—Zn—N1—C2−80.8 (2)C11—N4—C13—C18−2.1 (3)
N7—Zn—N1—C2−17.14 (18)C12—N4—C13—C18179.8 (3)
O1—Zn—N1—C90.7 (3)C11—N4—C13—C14174.6 (3)
N3—Zn—N1—C9−121.3 (3)C12—N4—C13—C14−3.4 (5)
N5—Zn—N1—C9108.7 (3)N4—C13—C14—C15−177.9 (3)
N7—Zn—N1—C9172.4 (3)C18—C13—C14—C15−1.6 (5)
O1—Zn—N3—C11148.31 (19)C13—C14—C15—C16−1.0 (5)
N1—Zn—N3—C11−85.0 (2)C14—C15—C16—C171.8 (6)
N5—Zn—N3—C1145.2 (2)C15—C16—C17—C180.1 (5)
N7—Zn—N3—C11−18.31 (19)C16—C17—C18—C13−2.6 (4)
O1—Zn—N3—C18−19.2 (3)C16—C17—C18—N3176.2 (3)
N1—Zn—N3—C18107.5 (2)N4—C13—C18—C17−179.4 (3)
N5—Zn—N3—C18−122.3 (2)C14—C13—C18—C173.5 (5)
N7—Zn—N3—C18174.2 (3)N4—C13—C18—N31.5 (3)
O1—Zn—N5—C20165.98 (18)C14—C13—C18—N3−175.6 (3)
N1—Zn—N5—C2045.3 (2)C11—N3—C18—C17−179.2 (3)
N3—Zn—N5—C20−82.75 (19)Zn—N3—C18—C17−10.7 (5)
N7—Zn—N5—C20−18.98 (17)C11—N3—C18—C13−0.3 (3)
O1—Zn—N5—C271.3 (2)Zn—N3—C18—C13168.3 (2)
N1—Zn—N5—C27−119.3 (2)C1—N7—C19—C20−145.2 (2)
N3—Zn—N5—C27112.6 (2)C10—N7—C19—C2084.4 (3)
N7—Zn—N5—C27176.3 (2)Zn—N7—C19—C20−29.9 (2)
O1—Zn—N7—C1169.7 (3)C27—N5—C20—N6−0.3 (3)
N1—Zn—N7—C125.38 (17)Zn—N5—C20—N6−168.96 (16)
N3—Zn—N7—C1−91.39 (17)C27—N5—C20—C19176.5 (2)
N5—Zn—N7—C1147.02 (18)Zn—N5—C20—C197.8 (3)
O1—Zn—N7—C10−70.4 (4)C22—N6—C20—N50.5 (3)
N1—Zn—N7—C10145.32 (18)C21—N6—C20—N5178.0 (2)
N3—Zn—N7—C1028.54 (16)C22—N6—C20—C19−176.2 (2)
N5—Zn—N7—C10−93.05 (17)C21—N6—C20—C191.3 (4)
O1—Zn—N7—C1949.8 (4)N7—C19—C20—N518.8 (3)
N1—Zn—N7—C19−94.54 (17)N7—C19—C20—N6−164.8 (2)
N3—Zn—N7—C19148.68 (18)C20—N6—C22—C23179.4 (3)
N5—Zn—N7—C1927.09 (16)C21—N6—C22—C231.9 (4)
C10—N7—C1—C2−142.1 (2)C20—N6—C22—C27−0.6 (3)
C19—N7—C1—C287.5 (3)C21—N6—C22—C27−178.0 (2)
Zn—N7—C1—C2−28.0 (2)N6—C22—C23—C24178.9 (3)
C9—N1—C2—N20.9 (3)C27—C22—C23—C24−1.1 (4)
Zn—N1—C2—N2−172.19 (18)C22—C23—C24—C251.3 (4)
C9—N1—C2—C1179.5 (2)C23—C24—C25—C26−0.8 (4)
Zn—N1—C2—C16.4 (3)C24—C25—C26—C270.1 (4)
C4—N2—C2—N1−0.2 (3)C20—N5—C27—C26179.8 (3)
C3—N2—C2—N1−177.5 (3)Zn—N5—C27—C26−14.0 (4)
C4—N2—C2—C1−178.8 (2)C20—N5—C27—C22−0.1 (3)
C3—N2—C2—C13.9 (4)Zn—N5—C27—C22166.01 (18)
N7—C1—C2—N118.5 (4)C25—C26—C27—N5−179.9 (3)
N7—C1—C2—N2−163.1 (2)C25—C26—C27—C220.0 (4)
C2—N2—C4—C9−0.6 (3)N6—C22—C27—N50.4 (3)
C3—N2—C4—C9176.6 (3)C23—C22—C27—N5−179.6 (2)
C2—N2—C4—C5−179.6 (3)N6—C22—C27—C26−179.5 (2)
C3—N2—C4—C5−2.4 (5)C23—C22—C27—C260.5 (4)
N2—C4—C5—C6177.9 (3)Zn—O1—C28—O24.6 (4)
C9—C4—C5—C6−1.0 (5)Zn—O1—C28—C29−172.9 (2)
C4—C5—C6—C70.2 (5)O2—C28—C29—C30−176.3 (3)
C5—C6—C7—C80.6 (5)O1—C28—C29—C301.4 (5)
C6—C7—C8—C9−0.5 (5)C28—C29—C30—C31178.5 (3)
C7—C8—C9—C4−0.3 (4)C29—C30—C31—C32−177.9 (3)
C7—C8—C9—N1−179.3 (3)C29—C30—C31—C361.9 (5)
N2—C4—C9—C8−178.0 (3)C36—C31—C32—C33−2.3 (4)
C5—C4—C9—C81.1 (4)C30—C31—C32—C33177.4 (3)
N2—C4—C9—N11.2 (3)C31—C32—C33—C341.4 (5)
C5—C4—C9—N1−179.7 (3)C32—C33—C34—O3179.6 (3)
C2—N1—C9—C8177.8 (3)C32—C33—C34—C350.3 (4)
Zn—N1—C9—C8−11.0 (5)O3—C34—C35—C36179.8 (3)
C2—N1—C9—C4−1.3 (3)C33—C34—C35—C36−0.8 (4)
Zn—N1—C9—C4170.0 (2)C34—C35—C36—C31−0.2 (5)
C1—N7—C10—C1181.8 (3)C32—C31—C36—C351.8 (4)
C19—N7—C10—C11−148.2 (2)C30—C31—C36—C35−178.0 (3)
Zn—N7—C10—C11−32.9 (2)C38—N8—C39—O82.8 (6)
C18—N3—C11—N4−1.1 (3)C37—N8—C39—O8−179.9 (4)
Zn—N3—C11—N4−172.02 (18)C42'—O10—C42—C41177.7 (5)
C18—N3—C11—C10175.6 (2)C42—O10—C42'—C41'176.5 (5)
Zn—N3—C11—C104.7 (3)
Symmetry codes: (i) −x, y, −z+1/2.
Acknowledgements top

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

references
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Sheldrick, G. M. (1997b). SHELXTL. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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