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

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ISSN: 2056-9890

Salicylato[tris­­(N-methyl­benzimidazol-2-ylmeth­yl)amine]zinc(II) perchlorate di­methyl­formamide sesquisolvate

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

(Received 19 October 2007; accepted 1 December 2007; online 6 December 2007)

In the title complex, [Zn(C7H5O3)(C27H27N7)]ClO4·1.5C3H7NO, the ZnII atom is five-coordinated by four N atoms from a tris­(N-methyl­benzimidazol-2-ylmeth­yl)amine ligand and one O atom from a salicylate ligand in a distorted trigonal-bipyramidal geometry (τ parameter = 0.84), with approximate mol­ecular C3 symmetry. One dimethyl­formamide mol­ecule lies on a general position and is disordered over two coplanar orientations with equal occupancy. A second dimethyl­formamide mol­ecule is disordered about a twofold rotation axis.

Related literature

For related literature, see: Addison et al. (1984[Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349-1356.]); Youngme et al. (2007[Youngme, S., Phatchimkun, J., Sukangpanya, U., Pakawatchai, C., Chaichit, N., Kongsaeree, P., Krzystek, J. & Murphy, B. (2007). Polyhedron, 26, 871-882.]).

[Scheme 1]

Experimental

Crystal data
  • [Zn(C7H5O3)(C27H27N7)]ClO4·1.5C3H7NO

  • Mr = 861.13

  • Monoclinic, C 2/c

  • a = 27.7110 (7) Å

  • b = 11.4499 (3) Å

  • c = 25.1395 (6) Å

  • β = 102.829 (1)°

  • V = 7777.3 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.77 mm−1

  • T = 153 (2) K

  • 0.78 × 0.59 × 0.52 mm

Data collection
  • Rigaku R-AXIS SPIDER diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.568, Tmax = 0.670

  • 37173 measured reflections

  • 8884 independent reflections

  • 7743 reflections with I > 2σ(I)

  • Rint = 0.024

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.142

  • S = 1.06

  • 8884 reflections

  • 544 parameters

  • 6 restraints

  • H-atom parameters constrained

  • Δρmax = 1.25 e Å−3

  • Δρmin = −0.89 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H3⋯O2 0.84 1.82 2.556 (3) 146

Data collection: RAPID-AUTO (Rigaku, 2004[Rigaku (2004). RAPID-AUTO. Version 3.0. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: SHELXTL (Bruker, 1997[Bruker (1997). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The asymmetric unit of the title compound consists of a discrete [Zn(Mentb)(salicylate)]+ cation (Mentb = tris(N-methylbenzimidazol-2-ylmethyl)amine) (Fig. 1), a perchlorate anion and 1.5 DMF molecules. The ZnII atom is five-coordinated with a N4O ligand set. The Mentb ligand acts as a tetradentate N-donor, and an O atom from the carboxylate group of the salicylate ligand completes the coordination. The geometry is best described as distorted trigonal bipyramidal (τ = 0.84, where β = O1—Zn—N7, α = N5—Zn—N1; Addison et al., 1984). The equatorial plane is occupied by three N atoms of three benzimidazolyl groups, while the ZnII atom is displaced towards O1 and is 0.560 (2) Å from the plane of atoms N1/N3/N5. The axial positions are occupyied by N7 and O1, with Zn—N7 = 2.434 (2) Å, Zn—O1 = 1.9974 (18) Å and O1—Zn—N7 = 165.76 (7) °. 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 113.00 (8), 115.30 (7) and 110.38 (8) °, respectively. The angles N7—Zn—N1 = 73.11 (7), N7—Zn—N3 = 74.69 (8) and N7—Zn—N5 = 74.93 (7) ° are all ca 16° less than the ideal value of 90°. This is imposed by the geometry of the Mentb ligand. The distance between ZnII and O2 is 3.136 (2) °, so O2 is not coordinated.

Related literature top

For related literature, see: Addison et al. (1984); 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)2.6H2O (0.0745 g, 0.2 mmol), followed by a solution of Na(salicylate) (0.0320 g, 0.2 mmol) in MeOH (5 ml). A colourless 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 give a colourless solution that was allowed to evaporate at room temperature. Colourless crystals suitable for X-ray analysis were obtained after two weeks. Yield 0.085 g (49%). Elemental analysis found: C 53.74, H 5.01, N 13.66; calculated: C 53.70, H 4.97, N 13.83.

Refinement top

All H atoms associated with the cation were visible in difference Fourier maps but were placed geometrically with C—H distances in the range 0.95–0.98 Å and O—H = 0.82 Å. They were allowed to ride during subsequent refinement with Uiso(H) = 1.2 or 1.5 Ueq(C/O). The DMF molecule on the general position is refined in two coplanar orientations, each with 50% site occupancy. The DMF molecule lying on the twofold rotation axis is modelled as one molecule with 50% site occupancy, with bond distances tightly restrained (C40—O9 = 1.200 (5), C40—N9 = 1.320 (5), N9—C37/C38 = 1.420 (5) Å) and the whole molecule restrained to be planar. The atoms of this molecule are refined with isotropic displacement parameters. The largest peak in the residual electron density (1.25 e Å-3) is associated with the perchlorate anion.

Structure description top

The asymmetric unit of the title compound consists of a discrete [Zn(Mentb)(salicylate)]+ cation (Mentb = tris(N-methylbenzimidazol-2-ylmethyl)amine) (Fig. 1), a perchlorate anion and 1.5 DMF molecules. The ZnII atom is five-coordinated with a N4O ligand set. The Mentb ligand acts as a tetradentate N-donor, and an O atom from the carboxylate group of the salicylate ligand completes the coordination. The geometry is best described as distorted trigonal bipyramidal (τ = 0.84, where β = O1—Zn—N7, α = N5—Zn—N1; Addison et al., 1984). The equatorial plane is occupied by three N atoms of three benzimidazolyl groups, while the ZnII atom is displaced towards O1 and is 0.560 (2) Å from the plane of atoms N1/N3/N5. The axial positions are occupyied by N7 and O1, with Zn—N7 = 2.434 (2) Å, Zn—O1 = 1.9974 (18) Å and O1—Zn—N7 = 165.76 (7) °. 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 113.00 (8), 115.30 (7) and 110.38 (8) °, respectively. The angles N7—Zn—N1 = 73.11 (7), N7—Zn—N3 = 74.69 (8) and N7—Zn—N5 = 74.93 (7) ° are all ca 16° less than the ideal value of 90°. This is imposed by the geometry of the Mentb ligand. The distance between ZnII and O2 is 3.136 (2) °, so O2 is not coordinated.

For related literature, see: Addison et al. (1984); Youngme et al. (2007).

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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures top
[Figure 1] Fig. 1. The [C34H32N7O3Zn]+ cation with displacement ellipsoids drawn at the 50% probability level. H atoms are omitted.
[Figure 2] Fig. 2. Packing diagram. H atoms are omitted for clarity.
Salicylato[tris(N-methylbenzimidazol-2-ylmethyl)amine]zinc(II) perchlorate dimethylformamide sesquisolvate top
Crystal data top
[Zn(C7H5O3)(C27H27N7)]ClO4·1.5C3H7NOF(000) = 3584
Mr = 861.13Dx = 1.471 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 30068 reflections
a = 27.7110 (7) Åθ = 3.0–27.5°
b = 11.4499 (3) ŵ = 0.77 mm1
c = 25.1395 (6) ÅT = 153 K
β = 102.829 (1)°Block, colourless
V = 7777.3 (3) Å30.78 × 0.59 × 0.52 mm
Z = 8
Data collection top
Rigaku R-AXIS Spider
diffractometer
8884 independent reflections
Radiation source: Rotating Anode7743 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: empirical (using intensity measurements)
(ABSCOR; Higashi, 1995)
h = 3534
Tmin = 0.568, Tmax = 0.670k = 1414
37173 measured reflectionsl = 3232
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0822P)2 + 15.4526P]
where P = (Fo2 + 2Fc2)/3
8884 reflections(Δ/σ)max = 0.002
544 parametersΔρmax = 1.25 e Å3
6 restraintsΔρmin = 0.89 e Å3
Crystal data top
[Zn(C7H5O3)(C27H27N7)]ClO4·1.5C3H7NOV = 7777.3 (3) Å3
Mr = 861.13Z = 8
Monoclinic, C2/cMo Kα radiation
a = 27.7110 (7) ŵ = 0.77 mm1
b = 11.4499 (3) ÅT = 153 K
c = 25.1395 (6) Å0.78 × 0.59 × 0.52 mm
β = 102.829 (1)°
Data collection top
Rigaku R-AXIS Spider
diffractometer
8884 independent reflections
Absorption correction: empirical (using intensity measurements)
(ABSCOR; Higashi, 1995)
7743 reflections with I > 2σ(I)
Tmin = 0.568, Tmax = 0.670Rint = 0.024
37173 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0476 restraints
wR(F2) = 0.142H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0822P)2 + 15.4526P]
where P = (Fo2 + 2Fc2)/3
8884 reflectionsΔρmax = 1.25 e Å3
544 parametersΔρmin = 0.89 e Å3
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)
Zn0.642944 (9)0.84620 (2)0.589173 (10)0.02240 (10)
O10.68899 (7)0.98268 (15)0.60013 (8)0.0327 (4)
O20.63215 (7)1.11523 (17)0.60677 (8)0.0335 (4)
O30.65424 (8)1.33229 (17)0.61367 (10)0.0452 (5)
H30.63561.27370.60800.068*
N10.69813 (7)0.73107 (17)0.57875 (7)0.0241 (4)
N20.72204 (8)0.58518 (18)0.53190 (8)0.0277 (4)
N30.61492 (7)0.80785 (19)0.65594 (8)0.0274 (4)
N40.58855 (8)0.6825 (2)0.71070 (9)0.0326 (5)
N50.58658 (7)0.87034 (17)0.52174 (8)0.0246 (4)
N60.51398 (7)0.81871 (19)0.46920 (8)0.0283 (4)
N70.60436 (7)0.65516 (17)0.57040 (8)0.0265 (4)
C10.63200 (9)0.5940 (2)0.53531 (10)0.0296 (5)
H1A0.61670.60930.49650.036*
H1B0.63130.50880.54170.036*
C20.68426 (9)0.6371 (2)0.54853 (9)0.0258 (5)
C30.71939 (11)0.4822 (2)0.49674 (11)0.0370 (6)
H3A0.68630.47720.47280.056*
H3B0.72580.41180.51940.056*
H3C0.74420.48890.47460.056*
C40.76425 (9)0.6482 (2)0.55369 (10)0.0278 (5)
C50.81354 (10)0.6319 (2)0.55133 (11)0.0358 (6)
H5A0.82340.56970.53110.043*
C60.84742 (10)0.7109 (3)0.57999 (12)0.0390 (6)
H6A0.88140.70260.57950.047*
C70.83287 (9)0.8028 (3)0.60969 (11)0.0343 (5)
H7A0.85720.85540.62880.041*
C80.78364 (9)0.8186 (2)0.61178 (10)0.0286 (5)
H8A0.77380.88090.63200.034*
C90.74914 (8)0.7397 (2)0.58307 (9)0.0246 (4)
C100.60888 (10)0.6025 (2)0.62449 (10)0.0320 (5)
H10A0.64150.56380.63620.038*
H10B0.58270.54310.62330.038*
C110.60377 (9)0.6977 (2)0.66370 (10)0.0286 (5)
C120.57507 (12)0.5739 (3)0.73413 (13)0.0446 (7)
H12A0.57090.51180.70660.067*
H12B0.54390.58480.74590.067*
H12C0.60130.55200.76560.067*
C130.59040 (9)0.7902 (3)0.73574 (10)0.0337 (5)
C140.57910 (12)0.8243 (3)0.78500 (12)0.0449 (7)
H14A0.56730.77020.80780.054*
C150.58600 (15)0.9400 (3)0.79865 (13)0.0559 (9)
H15A0.57920.96660.83200.067*
C160.60278 (15)1.0198 (3)0.76492 (13)0.0548 (9)
H16A0.60731.09900.77610.066*
C170.61307 (12)0.9863 (3)0.71506 (11)0.0412 (6)
H17A0.62381.04120.69180.049*
C180.60686 (9)0.8693 (2)0.70125 (10)0.0311 (5)
C190.55290 (9)0.6784 (2)0.54270 (10)0.0292 (5)
H19A0.53210.68650.56990.035*
H19B0.53980.61290.51800.035*
C200.55155 (8)0.7890 (2)0.51075 (9)0.0255 (4)
C210.47023 (9)0.7481 (3)0.44612 (11)0.0361 (6)
H21A0.46230.69800.47460.054*
H21B0.47700.69950.41650.054*
H21C0.44210.79970.43180.054*
C220.52469 (9)0.9281 (2)0.45136 (10)0.0287 (5)
C230.49815 (10)1.0003 (3)0.41024 (10)0.0357 (6)
H23A0.46680.97820.38870.043*
C240.51999 (11)1.1051 (3)0.40270 (10)0.0386 (6)
H24A0.50321.15690.37520.046*
C250.56648 (11)1.1380 (2)0.43449 (11)0.0361 (6)
H25A0.58061.21050.42750.043*
C260.59215 (10)1.0664 (2)0.47582 (10)0.0303 (5)
H26A0.62341.08890.49750.036*
C270.57034 (9)0.9600 (2)0.48429 (9)0.0266 (5)
C280.67578 (9)1.0869 (2)0.60680 (9)0.0274 (5)
C290.71459 (9)1.1799 (2)0.61504 (9)0.0270 (5)
C300.76458 (10)1.1524 (2)0.62053 (11)0.0344 (6)
H30A0.77391.07290.61860.041*
C310.80082 (11)1.2376 (3)0.62864 (12)0.0419 (6)
H31A0.83451.21730.63150.050*
C320.78700 (12)1.3540 (3)0.63254 (12)0.0423 (7)
H32A0.81161.41330.63850.051*
C330.73832 (11)1.3838 (2)0.62789 (11)0.0377 (6)
H33A0.72951.46330.63090.045*
C340.70162 (10)1.2980 (2)0.61868 (10)0.0318 (5)
O80.69099 (12)0.5249 (3)0.73406 (12)0.0713 (8)0.50
N80.71843 (9)0.3398 (2)0.75385 (10)0.0411 (6)0.50
C350.6706 (3)0.2884 (8)0.7451 (3)0.063 (2)0.50
H35A0.64530.34970.73670.095*0.50
H35B0.66710.24660.77810.095*0.50
H35C0.66620.23360.71450.095*0.50
C360.7606 (4)0.2671 (9)0.7667 (3)0.065 (2)0.50
H36A0.79060.31500.77140.098*0.50
H36B0.75980.21120.73700.098*0.50
H36C0.76070.22470.80060.098*0.50
C370.7223 (3)0.4587 (6)0.7472 (3)0.0459 (14)0.50
H37A0.75490.48940.75440.055*0.50
O8A0.69099 (12)0.5249 (3)0.73406 (12)0.0713 (8)0.50
N8A0.71843 (9)0.3398 (2)0.75385 (10)0.0411 (6)0.50
C35A0.7024 (3)0.2147 (6)0.7536 (3)0.0605 (19)0.50
H35D0.66620.21050.74330.091*0.50
H35E0.71400.18120.79000.091*0.50
H35F0.71640.17060.72720.091*0.50
C36A0.7705 (3)0.3607 (11)0.7684 (3)0.070 (3)0.50
H36D0.77680.44470.76730.106*0.50
H36E0.78660.32040.74260.106*0.50
H36F0.78390.33110.80530.106*0.50
C37A0.6847 (2)0.4201 (6)0.7380 (2)0.0434 (13)0.50
H37B0.65140.39370.72840.052*0.50
Cl0.55496 (2)0.47015 (6)0.39812 (3)0.04424 (18)
O40.55287 (14)0.5918 (3)0.3936 (3)0.138 (2)
O50.54976 (15)0.4453 (4)0.45323 (14)0.1082 (15)
O60.51871 (11)0.4007 (3)0.36312 (11)0.0824 (10)
O70.60198 (10)0.4316 (3)0.39497 (16)0.0792 (9)
O90.5677 (4)0.3054 (9)0.7066 (4)0.129 (3)*0.50
N90.50000.2510 (5)0.75000.1004 (19)*
C380.4819 (6)0.2026 (13)0.6968 (3)0.137 (5)*0.50
H38A0.50540.21860.67490.205*0.50
H38B0.47770.11970.69930.205*0.50
H38C0.45070.23790.68030.205*0.50
C390.4779 (5)0.2491 (11)0.7952 (4)0.130 (5)*0.50
H39A0.49900.28850.82530.195*0.50
H39B0.44640.28770.78620.195*0.50
H39C0.47340.16950.80520.195*0.50
C400.5431 (2)0.2957 (8)0.7421 (5)0.105 (4)*0.50
H40A0.56060.33240.77510.127*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.02145 (15)0.02387 (15)0.02202 (15)0.00371 (9)0.00515 (10)0.00118 (9)
O10.0295 (9)0.0263 (8)0.0419 (10)0.0001 (7)0.0071 (7)0.0061 (7)
O20.0291 (9)0.0330 (9)0.0372 (9)0.0053 (7)0.0047 (7)0.0021 (8)
O30.0413 (11)0.0296 (10)0.0596 (13)0.0084 (8)0.0002 (10)0.0013 (9)
N10.0234 (9)0.0259 (9)0.0233 (9)0.0055 (7)0.0059 (7)0.0002 (7)
N20.0313 (10)0.0286 (10)0.0245 (9)0.0082 (8)0.0092 (8)0.0014 (8)
N30.0259 (10)0.0322 (10)0.0249 (9)0.0029 (8)0.0071 (8)0.0002 (8)
N40.0295 (11)0.0393 (12)0.0298 (10)0.0036 (9)0.0087 (9)0.0072 (9)
N50.0241 (9)0.0265 (9)0.0238 (9)0.0054 (7)0.0069 (7)0.0002 (7)
N60.0216 (9)0.0347 (11)0.0277 (10)0.0056 (8)0.0032 (8)0.0040 (8)
N70.0255 (10)0.0257 (10)0.0283 (10)0.0046 (7)0.0062 (8)0.0007 (7)
C10.0283 (12)0.0286 (12)0.0307 (12)0.0046 (9)0.0038 (9)0.0057 (9)
C20.0293 (12)0.0257 (11)0.0224 (10)0.0088 (9)0.0058 (9)0.0014 (8)
C30.0478 (15)0.0342 (13)0.0303 (12)0.0124 (11)0.0112 (11)0.0058 (10)
C40.0315 (12)0.0307 (12)0.0235 (11)0.0070 (9)0.0114 (9)0.0040 (9)
C50.0347 (13)0.0404 (14)0.0376 (14)0.0125 (11)0.0196 (11)0.0055 (11)
C60.0271 (12)0.0509 (16)0.0432 (14)0.0072 (11)0.0167 (11)0.0094 (12)
C70.0264 (12)0.0414 (14)0.0367 (13)0.0004 (10)0.0101 (10)0.0069 (11)
C80.0287 (12)0.0316 (12)0.0265 (11)0.0024 (9)0.0085 (9)0.0055 (9)
C90.0247 (11)0.0287 (11)0.0220 (10)0.0065 (9)0.0085 (8)0.0070 (8)
C100.0351 (13)0.0272 (12)0.0337 (12)0.0050 (10)0.0076 (10)0.0048 (10)
C110.0233 (11)0.0351 (13)0.0263 (11)0.0049 (9)0.0035 (9)0.0048 (9)
C120.0470 (16)0.0453 (16)0.0446 (15)0.0019 (13)0.0168 (13)0.0162 (13)
C130.0287 (12)0.0442 (15)0.0292 (12)0.0026 (10)0.0088 (10)0.0030 (11)
C140.0477 (17)0.0611 (19)0.0303 (13)0.0009 (14)0.0182 (12)0.0038 (13)
C150.078 (2)0.061 (2)0.0372 (15)0.0008 (18)0.0312 (16)0.0073 (14)
C160.080 (2)0.0500 (18)0.0432 (16)0.0056 (17)0.0333 (17)0.0124 (14)
C170.0524 (17)0.0439 (15)0.0329 (13)0.0032 (13)0.0213 (12)0.0076 (11)
C180.0295 (12)0.0409 (14)0.0242 (11)0.0034 (10)0.0089 (10)0.0004 (10)
C190.0245 (11)0.0278 (11)0.0344 (12)0.0011 (9)0.0043 (9)0.0017 (9)
C200.0213 (10)0.0299 (11)0.0252 (10)0.0049 (9)0.0051 (8)0.0041 (9)
C210.0233 (11)0.0436 (15)0.0374 (13)0.0034 (10)0.0019 (10)0.0084 (11)
C220.0273 (11)0.0330 (12)0.0263 (11)0.0114 (9)0.0069 (9)0.0020 (9)
C230.0326 (13)0.0488 (15)0.0253 (11)0.0171 (11)0.0052 (10)0.0004 (11)
C240.0450 (15)0.0448 (15)0.0281 (12)0.0227 (12)0.0126 (11)0.0065 (11)
C250.0495 (16)0.0327 (13)0.0304 (12)0.0126 (11)0.0182 (12)0.0036 (10)
C260.0347 (12)0.0297 (12)0.0288 (11)0.0073 (10)0.0119 (10)0.0005 (9)
C270.0291 (11)0.0291 (11)0.0236 (10)0.0105 (9)0.0101 (9)0.0005 (9)
C280.0301 (12)0.0296 (12)0.0213 (10)0.0027 (9)0.0035 (9)0.0012 (9)
C290.0325 (12)0.0282 (11)0.0194 (10)0.0005 (9)0.0041 (9)0.0031 (8)
C300.0364 (14)0.0335 (13)0.0347 (13)0.0007 (10)0.0107 (11)0.0085 (10)
C310.0359 (14)0.0460 (16)0.0461 (15)0.0059 (12)0.0142 (12)0.0104 (13)
C320.0512 (17)0.0389 (15)0.0367 (14)0.0137 (12)0.0094 (13)0.0042 (11)
C330.0508 (16)0.0274 (12)0.0321 (13)0.0027 (11)0.0032 (12)0.0007 (10)
C340.0415 (14)0.0282 (12)0.0226 (11)0.0032 (10)0.0007 (10)0.0022 (9)
O80.082 (2)0.0578 (17)0.0711 (18)0.0077 (15)0.0106 (15)0.0054 (14)
N80.0391 (13)0.0522 (15)0.0294 (11)0.0040 (10)0.0025 (10)0.0025 (10)
C350.072 (5)0.068 (5)0.049 (4)0.033 (4)0.012 (3)0.014 (3)
C360.082 (6)0.074 (5)0.036 (3)0.031 (5)0.008 (3)0.004 (4)
C370.051 (4)0.041 (3)0.040 (3)0.005 (3)0.000 (3)0.000 (2)
O8A0.082 (2)0.0578 (17)0.0711 (18)0.0077 (15)0.0106 (15)0.0054 (14)
N8A0.0391 (13)0.0522 (15)0.0294 (11)0.0040 (10)0.0025 (10)0.0025 (10)
C35A0.097 (6)0.048 (4)0.037 (3)0.012 (4)0.016 (3)0.004 (3)
C36A0.030 (3)0.139 (9)0.039 (4)0.010 (4)0.002 (3)0.009 (5)
C37A0.033 (3)0.054 (4)0.040 (3)0.002 (3)0.003 (2)0.007 (3)
Cl0.0316 (3)0.0346 (3)0.0695 (5)0.0046 (2)0.0177 (3)0.0068 (3)
O40.079 (2)0.0514 (19)0.297 (7)0.0192 (16)0.071 (3)0.042 (3)
O50.115 (3)0.149 (3)0.073 (2)0.080 (3)0.0485 (19)0.056 (2)
O60.0594 (17)0.125 (3)0.0562 (16)0.0395 (18)0.0005 (13)0.0057 (17)
O70.0457 (14)0.0543 (15)0.146 (3)0.0046 (11)0.0397 (17)0.0089 (17)
Geometric parameters (Å, º) top
Zn—O11.9974 (18)C21—H21C0.980
Zn—N32.047 (2)C22—C271.398 (3)
Zn—N52.0528 (19)C22—C231.398 (3)
Zn—N12.0791 (18)C23—C241.376 (4)
Zn—N72.434 (2)C23—H23A0.950
O1—C281.270 (3)C24—C251.408 (4)
O2—C281.252 (3)C24—H24A0.950
O3—C341.349 (3)C25—C261.389 (4)
O3—H30.840C25—H25A0.950
N1—C21.323 (3)C26—C271.397 (4)
N1—C91.397 (3)C26—H26A0.950
N2—C21.349 (3)C28—C291.495 (3)
N2—C41.380 (3)C29—C301.397 (4)
N2—C31.465 (3)C29—C341.407 (3)
N3—C111.323 (3)C30—C311.383 (4)
N3—C181.399 (3)C30—H30A0.950
N4—C111.351 (3)C31—C321.397 (4)
N4—C131.381 (4)C31—H31A0.950
N4—C121.460 (4)C32—C331.371 (4)
N5—C201.329 (3)C32—H32A0.950
N5—C271.398 (3)C33—C341.396 (4)
N6—C201.344 (3)C33—H33A0.950
N6—C221.384 (3)O8—C371.144 (7)
N6—C211.465 (3)N8—C371.378 (7)
N7—C191.466 (3)N8—C361.412 (8)
N7—C101.467 (3)N8—C351.423 (7)
N7—C11.468 (3)C35—H35A0.980
C1—C21.496 (3)C35—H35B0.980
C1—H1A0.990C35—H35C0.980
C1—H1B0.990C36—H36A0.980
C3—H3A0.980C36—H36B0.980
C3—H3B0.980C36—H36C0.980
C3—H3C0.980C37—H37A0.950
C4—C51.393 (4)C35A—H35D0.980
C4—C91.399 (3)C35A—H35E0.980
C5—C61.386 (4)C35A—H35F0.980
C5—H5A0.950C36A—H36D0.980
C6—C71.400 (4)C36A—H36E0.980
C6—H6A0.950C36A—H36F0.980
C7—C81.389 (3)C37A—H37B0.950
C7—H7A0.950Cl—O71.394 (3)
C8—C91.394 (3)Cl—O41.398 (3)
C8—H8A0.950Cl—O61.423 (3)
C10—C111.498 (4)Cl—O51.453 (3)
C10—H10A0.990O9—C401.242 (5)
C10—H10B0.990O9—C39i1.410 (14)
C12—H12A0.980N9—C401.355 (5)
C12—H12B0.980N9—C40i1.355 (5)
C12—H12C0.980N9—C391.407 (5)
C13—C181.398 (4)N9—C39i1.407 (5)
C13—C141.399 (4)N9—C38i1.431 (5)
C14—C151.371 (5)N9—C381.431 (5)
C14—H14A0.950C38—C39i1.210 (17)
C15—C161.394 (5)C38—H38A0.960
C15—H15A0.950C38—H38B0.960
C16—C171.399 (4)C38—H38C0.960
C16—H16A0.950C39—C40i1.123 (15)
C17—C181.385 (4)C39—C38i1.210 (17)
C17—H17A0.950C39—O9i1.410 (14)
C19—C201.495 (3)C39—H39A0.960
C19—H19A0.990C39—H39B0.960
C19—H19B0.990C39—H39C0.960
C21—H21A0.980C40—C39i1.123 (15)
C21—H21B0.980C40—H40A0.960
O1—Zn—N3113.68 (8)N5—C20—N6112.8 (2)
O1—Zn—N5110.75 (8)N5—C20—C19123.5 (2)
N3—Zn—N5110.38 (8)N6—C20—C19123.7 (2)
O1—Zn—N192.77 (8)N6—C21—H21A109.5
N3—Zn—N1113.00 (8)N6—C21—H21B109.5
N5—Zn—N1115.30 (7)H21A—C21—H21B109.5
O1—Zn—N7165.76 (7)N6—C21—H21C109.5
N3—Zn—N774.69 (8)H21A—C21—H21C109.5
N5—Zn—N774.93 (7)H21B—C21—H21C109.5
N1—Zn—N773.11 (7)N6—C22—C27106.0 (2)
C28—O1—Zn123.99 (16)N6—C22—C23131.2 (2)
C34—O3—H3109.5C27—C22—C23122.8 (3)
C2—N1—C9105.19 (19)C24—C23—C22116.3 (3)
C2—N1—Zn117.37 (15)C24—C23—H23A121.9
C9—N1—Zn134.83 (16)C22—C23—H23A121.9
C2—N2—C4107.1 (2)C23—C24—C25122.0 (2)
C2—N2—C3127.1 (2)C23—C24—H24A119.0
C4—N2—C3125.8 (2)C25—C24—H24A119.0
C11—N3—C18106.0 (2)C26—C25—C24121.3 (3)
C11—N3—Zn117.96 (17)C26—C25—H25A119.4
C18—N3—Zn135.89 (18)C24—C25—H25A119.4
C11—N4—C13107.3 (2)C25—C26—C27117.5 (3)
C11—N4—C12128.3 (2)C25—C26—H26A121.3
C13—N4—C12124.4 (2)C27—C26—H26A121.3
C20—N5—C27105.27 (19)C26—C27—N5131.1 (2)
C20—N5—Zn117.65 (16)C26—C27—C22120.2 (2)
C27—N5—Zn136.64 (17)N5—C27—C22108.7 (2)
C20—N6—C22107.2 (2)O2—C28—O1123.4 (2)
C20—N6—C21126.7 (2)O2—C28—C29118.7 (2)
C22—N6—C21126.1 (2)O1—C28—C29117.9 (2)
C19—N7—C10112.9 (2)C30—C29—C34118.2 (2)
C19—N7—C1112.55 (19)C30—C29—C28121.3 (2)
C10—N7—C1114.34 (19)C34—C29—C28120.5 (2)
C19—N7—Zn105.54 (14)C31—C30—C29121.8 (3)
C10—N7—Zn104.26 (15)C31—C30—H30A119.1
C1—N7—Zn106.25 (15)C29—C30—H30A119.1
N7—C1—C2108.51 (19)C30—C31—C32118.9 (3)
N7—C1—H1A110.0C30—C31—H31A120.6
C2—C1—H1A110.0C32—C31—H31A120.6
N7—C1—H1B110.0C33—C32—C31120.8 (3)
C2—C1—H1B110.0C33—C32—H32A119.6
H1A—C1—H1B108.4C31—C32—H32A119.6
N1—C2—N2113.0 (2)C32—C33—C34120.4 (3)
N1—C2—C1122.6 (2)C32—C33—H33A119.8
N2—C2—C1124.4 (2)C34—C33—H33A119.8
N2—C3—H3A109.5O3—C34—C33117.9 (2)
N2—C3—H3B109.5O3—C34—C29122.1 (2)
H3A—C3—H3B109.5C33—C34—C29120.0 (3)
N2—C3—H3C109.5C37—N8—C36121.8 (6)
H3A—C3—H3C109.5C37—N8—C35118.9 (5)
H3B—C3—H3C109.5C36—N8—C35119.2 (7)
N2—C4—C5131.8 (2)N8—C35—H35A109.5
N2—C4—C9105.9 (2)N8—C35—H35B109.5
C5—C4—C9122.3 (2)H35A—C35—H35B109.5
C6—C5—C4116.6 (2)N8—C35—H35C109.5
C6—C5—H5A121.7H35A—C35—H35C109.5
C4—C5—H5A121.7H35B—C35—H35C109.5
C5—C6—C7121.7 (2)N8—C36—H36A109.5
C5—C6—H6A119.1N8—C36—H36B109.5
C7—C6—H6A119.1H36A—C36—H36B109.5
C8—C7—C6121.3 (3)N8—C36—H36C109.5
C8—C7—H7A119.3H36A—C36—H36C109.5
C6—C7—H7A119.3H36B—C36—H36C109.5
C7—C8—C9117.5 (2)O8—C37—N8128.0 (6)
C7—C8—H8A121.2O8—C37—H37A116.0
C9—C8—H8A121.2N8—C37—H37A116.0
C8—C9—N1130.7 (2)H35D—C35A—H35E109.5
C8—C9—C4120.5 (2)H35D—C35A—H35F109.5
N1—C9—C4108.8 (2)H35E—C35A—H35F109.5
N7—C10—C11108.0 (2)H36D—C36A—H36E109.5
N7—C10—H10A110.1H36D—C36A—H36F109.5
C11—C10—H10A110.1H36E—C36A—H36F109.5
N7—C10—H10B110.1O7—Cl—O4109.5 (2)
C11—C10—H10B110.1O7—Cl—O6109.2 (2)
H10A—C10—H10B108.4O4—Cl—O6119.8 (3)
N3—C11—N4112.3 (2)O7—Cl—O5106.5 (3)
N3—C11—C10122.5 (2)O4—Cl—O5105.2 (3)
N4—C11—C10125.1 (2)O6—Cl—O5105.92 (18)
N4—C12—H12A109.5C40—N9—C40i135.6 (8)
N4—C12—H12B109.5C40—N9—C39133.0 (8)
H12A—C12—H12B109.5C40i—N9—C39i133.0 (8)
N4—C12—H12C109.5C39—N9—C39i178.3 (10)
H12A—C12—H12C109.5C40—N9—C38i98.4 (8)
H12B—C12—H12C109.5C40i—N9—C38i98.4 (9)
N4—C13—C18106.3 (2)C39i—N9—C38i128.7 (8)
N4—C13—C14131.3 (3)C40—N9—C3898.4 (9)
C18—C13—C14122.4 (3)C40i—N9—C3898.4 (8)
C15—C14—C13116.4 (3)C39—N9—C38128.7 (9)
C15—C14—H14A121.8N9—C38—H38A108.7
C13—C14—H14A121.8C39i—C38—H38B123.0
C14—C15—C16121.8 (3)N9—C38—H38B110.1
C14—C15—H15A119.1H38A—C38—H38B109.5
C16—C15—H15A119.1N9—C38—H38C109.6
C15—C16—C17121.8 (3)H38A—C38—H38C109.5
C15—C16—H16A119.1H38B—C38—H38C109.5
C17—C16—H16A119.1C40i—C39—C38i129.4 (7)
C18—C17—C16116.8 (3)N9—C39—O9i121.0 (8)
C18—C17—H17A121.6C40i—C39—H39A123.2
C16—C17—H17A121.6N9—C39—H39A109.3
C17—C18—C13120.7 (2)O9i—C39—H39A101.3
C17—C18—N3131.1 (2)N9—C39—H39B109.8
C13—C18—N3108.2 (2)H39A—C39—H39B109.5
N7—C19—C20108.35 (19)N9—C39—H39C109.3
N7—C19—H19A110.0O9i—C39—H39C105.9
C20—C19—H19A110.0H39A—C39—H39C109.5
N7—C19—H19B110.0H39B—C39—H39C109.5
C20—C19—H19B110.0O9—C40—H40A109.3
H19A—C19—H19B108.4N9—C40—H40A109.3
N3—Zn—O1—C2866.4 (2)C18—C13—C14—C151.3 (5)
N5—Zn—O1—C2858.6 (2)C13—C14—C15—C160.8 (5)
N1—Zn—O1—C28176.99 (19)C14—C15—C16—C170.6 (6)
N7—Zn—O1—C28169.8 (2)C15—C16—C17—C181.4 (5)
O1—Zn—N1—C2152.64 (17)C16—C17—C18—C130.8 (4)
N3—Zn—N1—C290.15 (18)C16—C17—C18—N3178.3 (3)
N5—Zn—N1—C238.11 (19)N4—C13—C18—C17179.6 (2)
N7—Zn—N1—C225.52 (16)C14—C13—C18—C170.5 (4)
O1—Zn—N1—C95.9 (2)N4—C13—C18—N30.3 (3)
N3—Zn—N1—C9111.3 (2)C14—C13—C18—N3179.8 (2)
N5—Zn—N1—C9120.4 (2)C11—N3—C18—C17179.1 (3)
N7—Zn—N1—C9176.0 (2)Zn—N3—C18—C174.5 (4)
O1—Zn—N3—C11149.92 (17)C11—N3—C18—C130.1 (3)
N5—Zn—N3—C1184.94 (19)Zn—N3—C18—C13174.65 (18)
N1—Zn—N3—C1145.8 (2)C10—N7—C19—C20144.3 (2)
N7—Zn—N3—C1117.85 (17)C1—N7—C19—C2084.4 (2)
O1—Zn—N3—C1824.1 (3)Zn—N7—C19—C2031.1 (2)
N5—Zn—N3—C18101.0 (2)C27—N5—C20—N60.0 (3)
N1—Zn—N3—C18128.2 (2)Zn—N5—C20—N6173.71 (15)
N7—Zn—N3—C18168.1 (2)C27—N5—C20—C19177.7 (2)
O1—Zn—N5—C20176.78 (16)Zn—N5—C20—C194.0 (3)
N3—Zn—N5—C2049.99 (18)C22—N6—C20—N50.3 (3)
N1—Zn—N5—C2079.56 (18)C21—N6—C20—N5178.6 (2)
N7—Zn—N5—C2016.95 (16)C22—N6—C20—C19177.4 (2)
O1—Zn—N5—C275.7 (2)C21—N6—C20—C193.7 (4)
N3—Zn—N5—C27121.1 (2)N7—C19—C20—N522.1 (3)
N1—Zn—N5—C27109.3 (2)N7—C19—C20—N6160.4 (2)
N7—Zn—N5—C27172.0 (2)C20—N6—C22—C270.4 (2)
O1—Zn—N7—C19142.5 (3)C21—N6—C22—C27178.5 (2)
N3—Zn—N7—C1989.58 (16)C20—N6—C22—C23178.8 (3)
N5—Zn—N7—C1927.02 (15)C21—N6—C22—C232.3 (4)
N1—Zn—N7—C19150.00 (16)N6—C22—C23—C24179.5 (2)
O1—Zn—N7—C1098.4 (3)C27—C22—C23—C241.5 (4)
N3—Zn—N7—C1029.58 (14)C22—C23—C24—C250.1 (4)
N5—Zn—N7—C10146.17 (16)C23—C24—C25—C261.1 (4)
N1—Zn—N7—C1090.85 (15)C24—C25—C26—C270.6 (4)
O1—Zn—N7—C122.8 (4)C25—C26—C27—N5179.7 (2)
N3—Zn—N7—C1150.71 (16)C25—C26—C27—C220.8 (3)
N5—Zn—N7—C192.70 (15)C20—N5—C27—C26178.8 (2)
N1—Zn—N7—C130.28 (14)Zn—N5—C27—C269.4 (4)
C19—N7—C1—C2144.8 (2)C20—N5—C27—C220.2 (2)
C10—N7—C1—C284.7 (2)Zn—N5—C27—C22171.64 (17)
Zn—N7—C1—C229.7 (2)N6—C22—C27—C26178.8 (2)
C9—N1—C2—N21.2 (3)C23—C22—C27—C262.0 (4)
Zn—N1—C2—N2163.16 (15)N6—C22—C27—N50.3 (2)
C9—N1—C2—C1178.1 (2)C23—C22—C27—N5178.9 (2)
Zn—N1—C2—C117.5 (3)Zn—O1—C28—O20.6 (3)
C4—N2—C2—N11.3 (3)Zn—O1—C28—C29179.46 (15)
C3—N2—C2—N1178.0 (2)O2—C28—C29—C30174.0 (2)
C4—N2—C2—C1178.0 (2)O1—C28—C29—C306.1 (3)
C3—N2—C2—C12.7 (4)O2—C28—C29—C344.6 (3)
N7—C1—C2—N112.4 (3)O1—C28—C29—C34175.4 (2)
N7—C1—C2—N2166.8 (2)C34—C29—C30—C310.8 (4)
C2—N2—C4—C5177.6 (3)C28—C29—C30—C31179.4 (2)
C3—N2—C4—C53.1 (4)C29—C30—C31—C321.3 (4)
C2—N2—C4—C90.8 (2)C30—C31—C32—C330.6 (5)
C3—N2—C4—C9178.5 (2)C31—C32—C33—C340.5 (4)
N2—C4—C5—C6177.8 (3)C32—C33—C34—O3179.1 (3)
C9—C4—C5—C60.4 (4)C32—C33—C34—C291.1 (4)
C4—C5—C6—C70.2 (4)C30—C29—C34—O3179.8 (2)
C5—C6—C7—C80.1 (4)C28—C29—C34—O31.6 (4)
C6—C7—C8—C90.1 (4)C30—C29—C34—C330.4 (4)
C7—C8—C9—N1177.9 (2)C28—C29—C34—C33178.2 (2)
C7—C8—C9—C40.3 (3)C36—N8—C37—O8175.5 (6)
C2—N1—C9—C8177.1 (2)C35—N8—C37—O81.6 (9)
Zn—N1—C9—C822.6 (4)C40—N9—C38—C39i1.7 (11)
C2—N1—C9—C40.7 (2)C40i—N9—C38—C39i140.4 (12)
Zn—N1—C9—C4159.61 (17)C39—N9—C38—C39i178.1 (11)
N2—C4—C9—C8178.1 (2)C38i—N9—C38—C39i108.9 (11)
C5—C4—C9—C80.5 (4)C40—N9—C39—C40i118.3 (10)
N2—C4—C9—N10.0 (2)C38i—N9—C39—C40i177.7 (14)
C5—C4—C9—N1178.5 (2)C38—N9—C39—C40i62.0 (10)
C19—N7—C10—C1179.2 (2)C40—N9—C39—C38i59.4 (16)
C1—N7—C10—C11150.4 (2)C40i—N9—C39—C38i177.7 (14)
Zn—N7—C10—C1134.8 (2)C38—N9—C39—C38i120.2 (16)
C18—N3—C11—N40.5 (3)C40—N9—C39—O9i117.0 (14)
Zn—N3—C11—N4176.18 (15)C40i—N9—C39—O9i1.3 (7)
C18—N3—C11—C10178.3 (2)C38i—N9—C39—O9i176 (2)
Zn—N3—C11—C102.7 (3)C38—N9—C39—O9i63.4 (14)
C13—N4—C11—N30.7 (3)C39i—O9—C40—N92.0 (11)
C12—N4—C11—N3177.4 (2)C40i—N9—C40—C39i113.0 (9)
C13—N4—C11—C10178.1 (2)C39—N9—C40—C39i178.0 (11)
C12—N4—C11—C101.4 (4)C38i—N9—C40—C39i135.8 (10)
N7—C10—C11—N326.1 (3)C38—N9—C40—C39i1.8 (11)
N7—C10—C11—N4155.3 (2)C40i—N9—C40—O9110.9 (7)
C11—N4—C13—C180.5 (3)C39—N9—C40—O9179.9 (3)
C12—N4—C13—C18177.4 (2)C39i—N9—C40—O92.1 (11)
C11—N4—C13—C14179.5 (3)C38i—N9—C40—O9137.9 (11)
C12—N4—C13—C142.7 (5)C38—N9—C40—O90.3 (4)
N4—C13—C14—C15178.8 (3)
Symmetry code: (i) x+1, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.841.822.556 (3)146

Experimental details

Crystal data
Chemical formula[Zn(C7H5O3)(C27H27N7)]ClO4·1.5C3H7NO
Mr861.13
Crystal system, space groupMonoclinic, C2/c
Temperature (K)153
a, b, c (Å)27.7110 (7), 11.4499 (3), 25.1395 (6)
β (°) 102.829 (1)
V3)7777.3 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.77
Crystal size (mm)0.78 × 0.59 × 0.52
Data collection
DiffractometerRigaku R-AXIS Spider
Absorption correctionEmpirical (using intensity measurements)
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.568, 0.670
No. of measured, independent and
observed [I > 2σ(I)] reflections
37173, 8884, 7743
Rint0.024
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.142, 1.06
No. of reflections8884
No. of parameters544
No. of restraints6
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0822P)2 + 15.4526P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)1.25, 0.89

Computer programs: RAPID-AUTO (Rigaku, 2004), RAPID-AUTO (Rigaku, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.841.822.556 (3)145.9
 

Acknowledgements

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

References

First citationAddison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349–1356.  CSD CrossRef Web of Science Google Scholar
First citationBruker (1997). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku (2004). RAPID-AUTO. Version 3.0. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
First citationYoungme, S., Phatchimkun, J., Sukangpanya, U., Pakawatchai, C., Chaichit, N., Kongsaeree, P., Krzystek, J. & Murphy, B. (2007). Polyhedron, 26, 871–882.  Web of Science CSD CrossRef CAS Google Scholar

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