metal-organic compounds
Acrylato[tris(1-methylbenzimidazol-2-ylmethyl)amine]zinc(II) perchlorate–dimethylformamide–methanol (1/1/1.5) at 153 (2) K
aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
*Correspondence e-mail: wuhuilu@163.com
In the title complex, [Zn(C3H3O2)(C27H27N7)](ClO4)·C3H7NO·1.5CH4O, the ZnII ion is five-coordinated by four N atoms from a tris(1-methylbenzimidazol-2-ylmethyl)amine (Mentb) ligand and one O atom from an acrylate ligand in a distorted trigonal–bipyramidal geometry with approximate molecular C3 symmetry. The atoms of the acrylate ligand are disordered over two sites, with approximate occupancies of 0.84 and 0.16. In addition, a methanol solvent molecule is disordered over two sites with equal occupancies. In the the full-occupancy methanol is linked to a dimethylformamide molecule by an intermolecular O—H⋯O hydrogen bond.
Related literature
For related literature, see: Youngme et al. (2007). For bond-length data, see: Allen et al. (1987).
Experimental
Crystal data
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Refinement
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Data collection: RAPID-AUTO (Rigaku/MSC 2004); cell RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Bruker, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536807068675/lh2580sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536807068675/lh2580Isup2.hkl
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 (H2O)6 (0.0745 g, 0.2 mmol), followed by a solution of Na(acrylate) (0.0188 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 two weeks. Yield, 0.092 g (57%). (found: C, 51.20; H, 5.08; N,13.76. Calcd. for C34.50H43ClN8O8.50Zn: C, 51.37; H, 5.37; N, 13.89)
The atoms of the acrylate ligand are disordered over two sites with refined occupancies of 0.836 (5) and 0.164 (5) for the minimum and maximum components, respectively. The 0.5 occupancy methanol molecule is disordered over two sites with equal occupancies. All H atoms were found in difference electron maps and were subsequently refined in a riding-model approximation with C—H distances ranging from 0.95 to 0.99 Å and O—H distance 0.84 Å and Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(Cmethyl or O).
Data collection: RAPID-AUTO (Rigaku/MSC 2004); cell
RAPID-AUTO (Rigaku/MSC 2004); data reduction: RAPID-AUTO (Rigaku/MSC 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 1997).[Zn(C3H3O2)(C27H27N7)](ClO4)·C3H7NO·1.5CH4O | Z = 2 |
Mr = 806.61 | F(000) = 842 |
Triclinic, P1 | Dx = 1.397 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.3766 (4) Å | Cell parameters from 16325 reflections |
b = 13.9606 (4) Å | θ = 3.0–27.5° |
c = 14.4355 (5) Å | µ = 0.77 mm−1 |
α = 108.579 (1)° | T = 153 K |
β = 111.011 (1)° | Block, colorless |
γ = 100.075 (1)° | 0.59 × 0.56 × 0.40 mm |
V = 1917.33 (11) Å3 |
Rigaku R-axis SPIDER diffractometer | 8711 independent reflections |
Radiation source: Rotating Anode | 7735 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (Higashi; 1995) | h = −14→14 |
Tmin = 0.659, Tmax = 0.748 | k = −18→17 |
18907 measured reflections | l = −18→18 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.088P)2 + 1.5221P] where P = (Fo2 + 2Fc2)/3 |
8711 reflections | (Δ/σ)max = 0.001 |
523 parameters | Δρmax = 1.29 e Å−3 |
28 restraints | Δρmin = −0.74 e Å−3 |
[Zn(C3H3O2)(C27H27N7)](ClO4)·C3H7NO·1.5CH4O | γ = 100.075 (1)° |
Mr = 806.61 | V = 1917.33 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 11.3766 (4) Å | Mo Kα radiation |
b = 13.9606 (4) Å | µ = 0.77 mm−1 |
c = 14.4355 (5) Å | T = 153 K |
α = 108.579 (1)° | 0.59 × 0.56 × 0.40 mm |
β = 111.011 (1)° |
Rigaku R-axis SPIDER diffractometer | 8711 independent reflections |
Absorption correction: multi-scan (Higashi; 1995) | 7735 reflections with I > 2σ(I) |
Tmin = 0.659, Tmax = 0.748 | Rint = 0.024 |
18907 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 28 restraints |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 1.05 | Δρmax = 1.29 e Å−3 |
8711 reflections | Δρmin = −0.74 e Å−3 |
523 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn | 0.35354 (2) | 0.15960 (2) | 0.32037 (2) | 0.02210 (10) | |
N1 | 0.43780 (19) | 0.29536 (15) | 0.46350 (16) | 0.0226 (4) | |
N2 | 0.4269 (2) | 0.41504 (16) | 0.60253 (17) | 0.0259 (4) | |
N3 | 0.16855 (19) | 0.14640 (15) | 0.21459 (15) | 0.0230 (4) | |
N4 | −0.05296 (19) | 0.08379 (15) | 0.14418 (16) | 0.0249 (4) | |
N5 | 0.3625 (2) | 0.02424 (16) | 0.34902 (16) | 0.0250 (4) | |
N6 | 0.3172 (2) | −0.08938 (17) | 0.42042 (17) | 0.0288 (4) | |
N7 | 0.21188 (19) | 0.14020 (15) | 0.41159 (16) | 0.0233 (4) | |
C1 | 0.2265 (2) | 0.24986 (19) | 0.4776 (2) | 0.0262 (5) | |
H1A | 0.2102 | 0.2524 | 0.5411 | 0.031* | |
H1B | 0.1609 | 0.2751 | 0.4335 | 0.031* | |
C2 | 0.3647 (2) | 0.31989 (18) | 0.51553 (19) | 0.0235 (4) | |
C3 | 0.3742 (3) | 0.4680 (2) | 0.6758 (2) | 0.0363 (6) | |
H3A | 0.2768 | 0.4443 | 0.6369 | 0.054* | |
H3B | 0.4098 | 0.5456 | 0.7010 | 0.054* | |
H3C | 0.4007 | 0.4496 | 0.7387 | 0.054* | |
C4 | 0.5506 (2) | 0.45659 (19) | 0.6080 (2) | 0.0258 (5) | |
C5 | 0.6552 (3) | 0.5515 (2) | 0.6807 (2) | 0.0337 (5) | |
H5A | 0.6503 | 0.6026 | 0.7400 | 0.040* | |
C6 | 0.7666 (3) | 0.5675 (2) | 0.6621 (2) | 0.0371 (6) | |
H6A | 0.8405 | 0.6309 | 0.7103 | 0.045* | |
C7 | 0.7735 (3) | 0.4929 (2) | 0.5744 (2) | 0.0357 (6) | |
H7A | 0.8516 | 0.5072 | 0.5641 | 0.043* | |
C8 | 0.6690 (2) | 0.3983 (2) | 0.5020 (2) | 0.0282 (5) | |
H8A | 0.6740 | 0.3475 | 0.4426 | 0.034* | |
C9 | 0.5564 (2) | 0.38108 (18) | 0.52022 (19) | 0.0238 (4) | |
C10 | 0.0769 (2) | 0.07969 (19) | 0.32346 (19) | 0.0254 (5) | |
H10A | 0.0104 | 0.0998 | 0.3480 | 0.030* | |
H10B | 0.0603 | 0.0021 | 0.3028 | 0.030* | |
C11 | 0.0646 (2) | 0.10465 (17) | 0.22763 (19) | 0.0230 (4) | |
C12 | −0.1853 (2) | 0.0394 (2) | 0.1352 (2) | 0.0323 (5) | |
H12A | −0.1830 | −0.0124 | 0.1678 | 0.048* | |
H12B | −0.2502 | 0.0036 | 0.0581 | 0.048* | |
H12C | −0.2111 | 0.0973 | 0.1735 | 0.048* | |
C13 | −0.0252 (2) | 0.11589 (17) | 0.07074 (19) | 0.0248 (4) | |
C14 | −0.1086 (3) | 0.1126 (2) | −0.0289 (2) | 0.0303 (5) | |
H14A | −0.2028 | 0.0845 | −0.0587 | 0.036* | |
C15 | −0.0471 (3) | 0.1523 (2) | −0.0823 (2) | 0.0338 (5) | |
H15A | −0.1005 | 0.1523 | −0.1501 | 0.041* | |
C16 | 0.0931 (3) | 0.1928 (2) | −0.0383 (2) | 0.0335 (5) | |
H16A | 0.1318 | 0.2195 | −0.0772 | 0.040* | |
C17 | 0.1751 (3) | 0.19458 (19) | 0.06038 (19) | 0.0279 (5) | |
H17A | 0.2693 | 0.2217 | 0.0897 | 0.033* | |
C18 | 0.1145 (2) | 0.15516 (18) | 0.11509 (18) | 0.0241 (4) | |
C19 | 0.2620 (2) | 0.0809 (2) | 0.4757 (2) | 0.0274 (5) | |
H19A | 0.1895 | 0.0409 | 0.4852 | 0.033* | |
H19B | 0.3340 | 0.1307 | 0.5487 | 0.033* | |
C20 | 0.3142 (2) | 0.0051 (2) | 0.41521 (19) | 0.0259 (5) | |
C21 | 0.2753 (3) | −0.1350 (2) | 0.4862 (2) | 0.0375 (6) | |
H21A | 0.2256 | −0.0941 | 0.5159 | 0.056* | |
H21B | 0.3540 | −0.1319 | 0.5462 | 0.056* | |
H21C | 0.2182 | −0.2097 | 0.4405 | 0.056* | |
C22 | 0.3701 (2) | −0.1366 (2) | 0.3518 (2) | 0.0290 (5) | |
C23 | 0.3908 (3) | −0.2346 (2) | 0.3233 (2) | 0.0381 (6) | |
H23A | 0.3668 | −0.2842 | 0.3510 | 0.046* | |
C24 | 0.4480 (3) | −0.2564 (2) | 0.2530 (2) | 0.0438 (7) | |
H24A | 0.4641 | −0.3227 | 0.2319 | 0.053* | |
C25 | 0.4830 (3) | −0.1842 (2) | 0.2118 (2) | 0.0417 (7) | |
H25A | 0.5244 | −0.2015 | 0.1650 | 0.050* | |
C26 | 0.4583 (3) | −0.0871 (2) | 0.2381 (2) | 0.0332 (5) | |
H26A | 0.4804 | −0.0385 | 0.2087 | 0.040* | |
C27 | 0.4004 (2) | −0.06388 (19) | 0.30861 (19) | 0.0266 (5) | |
C28 | 0.4818 (2) | 0.1641 (2) | 0.18395 (19) | 0.0314 (5) | |
O1 | 0.4880 (2) | 0.21199 (19) | 0.27462 (17) | 0.0352 (6) | 0.836 (5) |
O2 | 0.4042 (2) | 0.06708 (18) | 0.12040 (18) | 0.0360 (6) | 0.836 (5) |
C29 | 0.5724 (3) | 0.2162 (3) | 0.1495 (3) | 0.0322 (7) | 0.836 (5) |
H29 | 0.6360 | 0.2843 | 0.2008 | 0.039* | 0.836 (5) |
C30 | 0.5724 (4) | 0.1770 (3) | 0.0555 (3) | 0.0584 (9) | |
H30A | 0.5104 | 0.1092 | 0.0019 | 0.070* | 0.836 (5) |
H30B | 0.6344 | 0.2161 | 0.0400 | 0.070* | 0.836 (5) |
O1' | 0.4269 (12) | 0.1035 (7) | 0.2132 (10) | 0.052 (4) | 0.164 (5) |
O2' | 0.4857 (14) | 0.2630 (5) | 0.2149 (10) | 0.061 (5) | 0.164 (5) |
C29' | 0.5255 (19) | 0.1223 (7) | 0.0992 (12) | 0.070 (9) | 0.164 (5) |
H29' | 0.5187 | 0.0489 | 0.0745 | 0.084* | 0.164 (5) |
H30C | 0.5809 | 0.2507 | 0.0778 | 0.070* | 0.164 (5) |
H30D | 0.5983 | 0.1436 | 0.0011 | 0.070* | 0.164 (5) |
O9 | −0.3164 (15) | −0.4481 (12) | −0.0180 (13) | 0.097 (4) | 0.25 |
H9A | −0.3562 | −0.4937 | −0.0841 | 0.145* | 0.25 |
C35 | −0.404 (3) | −0.498 (2) | 0.020 (2) | 0.108 (6) | 0.25 |
H35A | −0.3769 | −0.4534 | 0.0966 | 0.161* | 0.25 |
H35B | −0.3972 | −0.5691 | 0.0121 | 0.161* | 0.25 |
H35C | −0.4964 | −0.5054 | −0.0242 | 0.161* | 0.25 |
O9' | −0.4896 (14) | −0.5339 (13) | −0.0429 (14) | 0.098 (4) | 0.25 |
H9'A | −0.5219 | −0.5595 | −0.1120 | 0.147* | 0.25 |
C35' | −0.3528 (2) | −0.45924 (15) | 0.00898 (18) | 0.108 (6) | 0.25 |
H35D | −0.3532 | −0.3997 | −0.0130 | 0.161* | 0.25 |
H35E | −0.2961 | −0.4968 | −0.0140 | 0.161* | 0.25 |
H35F | −0.3180 | −0.4316 | 0.0884 | 0.161* | 0.25 |
O7 | 1.1335 (2) | 0.55543 (15) | 0.72271 (18) | 0.0648 (7) | |
N10 | 1.0423 (2) | 0.51106 (15) | 0.82520 (18) | 0.0563 (7) | |
C31 | 0.9669 (2) | 0.42510 (15) | 0.84068 (18) | 0.100 (2) | |
H31A | 0.9486 | 0.3558 | 0.7833 | 0.150* | |
H31B | 0.8827 | 0.4357 | 0.8368 | 0.150* | |
H31C | 1.0195 | 0.4268 | 0.9122 | 0.150* | |
C32 | 1.0725 (5) | 0.6191 (3) | 0.8999 (4) | 0.0653 (10) | |
H32A | 1.1206 | 0.6690 | 0.8806 | 0.098* | |
H32B | 1.1281 | 0.6291 | 0.9743 | 0.098* | |
H32C | 0.9895 | 0.6328 | 0.8955 | 0.098* | |
C33 | 1.0770 (4) | 0.4894 (3) | 0.7448 (3) | 0.0534 (8) | |
H33A | 1.0563 | 0.4162 | 0.7003 | 0.064* | |
O8 | −0.0521 (2) | 0.28742 (17) | 0.33417 (18) | 0.0412 (5) | |
H8O | −0.0767 | 0.3351 | 0.3169 | 0.062* | |
C34 | −0.1037 (4) | 0.2828 (4) | 0.4076 (4) | 0.0650 (11) | |
H34A | −0.0733 | 0.2337 | 0.4388 | 0.097* | |
H34B | −0.2013 | 0.2572 | 0.3693 | 0.097* | |
H34C | −0.0728 | 0.3543 | 0.4661 | 0.097* | |
Cl | −0.10330 (7) | −0.17834 (5) | 0.32322 (6) | 0.03704 (16) | |
O3 | −0.1742 (3) | −0.1134 (3) | 0.2867 (3) | 0.0787 (10) | |
O4 | −0.1929 (3) | −0.2823 (2) | 0.2867 (2) | 0.0705 (8) | |
O5 | −0.0381 (2) | −0.1306 (2) | 0.44072 (19) | 0.0566 (6) | |
O6 | −0.0026 (2) | −0.1836 (2) | 0.28517 (18) | 0.0489 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn | 0.02388 (15) | 0.02273 (15) | 0.02353 (15) | 0.00978 (10) | 0.01317 (11) | 0.01000 (11) |
N1 | 0.0230 (9) | 0.0219 (9) | 0.0252 (9) | 0.0086 (7) | 0.0122 (8) | 0.0103 (8) |
N2 | 0.0308 (10) | 0.0231 (10) | 0.0286 (10) | 0.0124 (8) | 0.0160 (8) | 0.0113 (8) |
N3 | 0.0266 (9) | 0.0198 (9) | 0.0219 (9) | 0.0067 (7) | 0.0115 (8) | 0.0076 (7) |
N4 | 0.0239 (9) | 0.0212 (9) | 0.0255 (9) | 0.0068 (7) | 0.0087 (8) | 0.0076 (8) |
N5 | 0.0283 (10) | 0.0239 (9) | 0.0265 (9) | 0.0112 (8) | 0.0136 (8) | 0.0117 (8) |
N6 | 0.0297 (10) | 0.0309 (11) | 0.0319 (10) | 0.0132 (8) | 0.0130 (9) | 0.0192 (9) |
N7 | 0.0231 (9) | 0.0233 (9) | 0.0239 (9) | 0.0083 (7) | 0.0110 (8) | 0.0094 (8) |
C1 | 0.0280 (11) | 0.0257 (11) | 0.0296 (11) | 0.0105 (9) | 0.0179 (10) | 0.0101 (9) |
C2 | 0.0253 (11) | 0.0244 (11) | 0.0248 (10) | 0.0111 (9) | 0.0127 (9) | 0.0114 (9) |
C3 | 0.0470 (15) | 0.0295 (13) | 0.0374 (14) | 0.0153 (11) | 0.0273 (13) | 0.0086 (11) |
C4 | 0.0283 (11) | 0.0226 (11) | 0.0312 (12) | 0.0109 (9) | 0.0137 (10) | 0.0151 (9) |
C5 | 0.0409 (14) | 0.0198 (11) | 0.0373 (13) | 0.0093 (10) | 0.0159 (12) | 0.0102 (10) |
C6 | 0.0340 (13) | 0.0223 (12) | 0.0452 (15) | 0.0015 (10) | 0.0127 (12) | 0.0120 (11) |
C7 | 0.0305 (13) | 0.0283 (13) | 0.0507 (16) | 0.0069 (10) | 0.0186 (12) | 0.0201 (12) |
C8 | 0.0277 (11) | 0.0246 (11) | 0.0380 (13) | 0.0109 (9) | 0.0165 (10) | 0.0163 (10) |
C9 | 0.0249 (11) | 0.0217 (11) | 0.0297 (11) | 0.0107 (8) | 0.0115 (9) | 0.0158 (9) |
C10 | 0.0232 (11) | 0.0256 (11) | 0.0281 (11) | 0.0068 (9) | 0.0118 (9) | 0.0123 (9) |
C11 | 0.0246 (11) | 0.0177 (10) | 0.0249 (10) | 0.0073 (8) | 0.0105 (9) | 0.0070 (8) |
C12 | 0.0242 (11) | 0.0331 (13) | 0.0358 (13) | 0.0075 (9) | 0.0120 (10) | 0.0125 (11) |
C13 | 0.0282 (11) | 0.0161 (10) | 0.0258 (11) | 0.0067 (8) | 0.0106 (9) | 0.0054 (8) |
C14 | 0.0316 (12) | 0.0240 (11) | 0.0268 (11) | 0.0098 (9) | 0.0072 (10) | 0.0066 (9) |
C15 | 0.0433 (14) | 0.0298 (13) | 0.0242 (11) | 0.0138 (11) | 0.0109 (11) | 0.0098 (10) |
C16 | 0.0443 (15) | 0.0304 (13) | 0.0280 (12) | 0.0122 (11) | 0.0178 (11) | 0.0127 (10) |
C17 | 0.0338 (12) | 0.0235 (11) | 0.0245 (11) | 0.0090 (9) | 0.0127 (10) | 0.0084 (9) |
C18 | 0.0288 (11) | 0.0188 (10) | 0.0218 (10) | 0.0086 (8) | 0.0096 (9) | 0.0062 (8) |
C19 | 0.0314 (12) | 0.0311 (12) | 0.0270 (11) | 0.0139 (10) | 0.0164 (10) | 0.0151 (10) |
C20 | 0.0243 (11) | 0.0298 (12) | 0.0258 (11) | 0.0112 (9) | 0.0092 (9) | 0.0152 (9) |
C21 | 0.0387 (14) | 0.0441 (15) | 0.0445 (15) | 0.0166 (12) | 0.0200 (12) | 0.0328 (13) |
C22 | 0.0271 (12) | 0.0303 (12) | 0.0280 (12) | 0.0129 (9) | 0.0072 (10) | 0.0143 (10) |
C23 | 0.0460 (15) | 0.0334 (14) | 0.0358 (14) | 0.0202 (12) | 0.0112 (12) | 0.0195 (11) |
C24 | 0.0578 (18) | 0.0359 (15) | 0.0364 (14) | 0.0306 (14) | 0.0127 (14) | 0.0147 (12) |
C25 | 0.0546 (18) | 0.0435 (16) | 0.0324 (13) | 0.0323 (14) | 0.0191 (13) | 0.0140 (12) |
C26 | 0.0417 (14) | 0.0348 (14) | 0.0301 (12) | 0.0221 (11) | 0.0176 (11) | 0.0149 (11) |
C27 | 0.0268 (11) | 0.0266 (11) | 0.0253 (11) | 0.0128 (9) | 0.0081 (9) | 0.0113 (9) |
C28 | 0.0234 (11) | 0.0411 (15) | 0.0286 (12) | 0.0079 (10) | 0.0108 (10) | 0.0153 (11) |
O1 | 0.0306 (11) | 0.0413 (14) | 0.0298 (11) | 0.0043 (9) | 0.0180 (9) | 0.0088 (10) |
O2 | 0.0367 (12) | 0.0289 (11) | 0.0314 (12) | 0.0018 (9) | 0.0102 (10) | 0.0095 (9) |
C29 | 0.0296 (15) | 0.0387 (17) | 0.0360 (16) | 0.0113 (13) | 0.0201 (13) | 0.0182 (14) |
C30 | 0.060 (2) | 0.085 (3) | 0.054 (2) | 0.0269 (19) | 0.0396 (18) | 0.040 (2) |
C28' | 0.0234 (11) | 0.0411 (15) | 0.0286 (12) | 0.0079 (10) | 0.0108 (10) | 0.0153 (11) |
O1' | 0.051 (8) | 0.093 (12) | 0.061 (9) | 0.044 (8) | 0.047 (7) | 0.057 (9) |
O2' | 0.046 (8) | 0.079 (12) | 0.044 (8) | −0.008 (7) | 0.017 (7) | 0.026 (8) |
C29' | 0.044 (12) | 0.14 (3) | 0.070 (16) | 0.049 (15) | 0.035 (12) | 0.079 (19) |
C30' | 0.060 (2) | 0.085 (3) | 0.054 (2) | 0.0269 (19) | 0.0396 (18) | 0.040 (2) |
O9 | 0.106 (6) | 0.085 (6) | 0.089 (6) | 0.002 (4) | 0.036 (4) | 0.048 (5) |
C35 | 0.105 (7) | 0.116 (8) | 0.096 (7) | 0.020 (5) | 0.058 (5) | 0.030 (5) |
O9' | 0.083 (6) | 0.114 (6) | 0.095 (6) | 0.038 (4) | 0.039 (4) | 0.039 (4) |
C35' | 0.105 (7) | 0.116 (8) | 0.096 (7) | 0.020 (5) | 0.058 (5) | 0.030 (5) |
O7 | 0.0665 (16) | 0.0675 (17) | 0.101 (2) | 0.0383 (14) | 0.0541 (16) | 0.0547 (17) |
N10 | 0.0695 (19) | 0.0356 (14) | 0.0688 (19) | 0.0159 (13) | 0.0407 (17) | 0.0167 (13) |
C31 | 0.152 (5) | 0.049 (2) | 0.122 (4) | 0.015 (3) | 0.102 (4) | 0.024 (3) |
C32 | 0.078 (3) | 0.0409 (19) | 0.069 (2) | 0.0217 (18) | 0.034 (2) | 0.0109 (17) |
C33 | 0.062 (2) | 0.0419 (17) | 0.068 (2) | 0.0253 (15) | 0.0372 (19) | 0.0233 (16) |
O8 | 0.0394 (11) | 0.0405 (11) | 0.0539 (12) | 0.0173 (9) | 0.0283 (10) | 0.0206 (10) |
C34 | 0.069 (2) | 0.093 (3) | 0.080 (3) | 0.052 (2) | 0.055 (2) | 0.052 (2) |
Cl | 0.0412 (4) | 0.0373 (3) | 0.0420 (4) | 0.0115 (3) | 0.0224 (3) | 0.0240 (3) |
O3 | 0.0457 (14) | 0.100 (2) | 0.134 (3) | 0.0352 (15) | 0.0412 (17) | 0.092 (2) |
O4 | 0.092 (2) | 0.0420 (14) | 0.0653 (17) | −0.0064 (13) | 0.0423 (16) | 0.0146 (12) |
O5 | 0.0525 (14) | 0.0726 (17) | 0.0428 (12) | 0.0167 (12) | 0.0285 (11) | 0.0151 (12) |
O6 | 0.0566 (13) | 0.0657 (15) | 0.0430 (11) | 0.0255 (11) | 0.0333 (11) | 0.0290 (11) |
Zn—O1 | 1.988 (2) | C19—C20 | 1.495 (3) |
Zn—O1' | 2.021 (7) | C19—H19A | 0.9900 |
Zn—N3 | 2.0433 (19) | C19—H19B | 0.9900 |
Zn—N1 | 2.0564 (19) | C21—H21A | 0.9800 |
Zn—N5 | 2.071 (2) | C21—H21B | 0.9800 |
Zn—N7 | 2.4497 (19) | C21—H21C | 0.9800 |
N1—C2 | 1.326 (3) | C22—C23 | 1.386 (4) |
N1—C9 | 1.393 (3) | C22—C27 | 1.405 (3) |
N2—C2 | 1.347 (3) | C23—C24 | 1.376 (4) |
N2—C4 | 1.389 (3) | C23—H23A | 0.9500 |
N2—C3 | 1.462 (3) | C24—C25 | 1.392 (5) |
N3—C11 | 1.328 (3) | C24—H24A | 0.9500 |
N3—C18 | 1.400 (3) | C25—C26 | 1.394 (4) |
N4—C11 | 1.345 (3) | C25—H25A | 0.9500 |
N4—C13 | 1.385 (3) | C26—C27 | 1.386 (4) |
N4—C12 | 1.466 (3) | C26—H26A | 0.9500 |
N5—C20 | 1.332 (3) | C28—O1 | 1.235 (3) |
N5—C27 | 1.396 (3) | C28—O2 | 1.290 (3) |
N6—C20 | 1.351 (3) | C28—C29 | 1.474 (4) |
N6—C22 | 1.388 (3) | C29—C30 | 1.292 (5) |
N6—C21 | 1.463 (3) | C29—H29 | 0.9500 |
N7—C19 | 1.464 (3) | C30—H30A | 0.9500 |
N7—C1 | 1.465 (3) | C30—H30B | 0.9500 |
N7—C10 | 1.466 (3) | C29'—H29' | 0.9500 |
C1—C2 | 1.493 (3) | O9—C35 | 1.473 (15) |
C1—H1A | 0.9900 | O9—H9A | 0.8500 |
C1—H1B | 0.9900 | C35—H35A | 0.9800 |
C3—H3A | 0.9800 | C35—H35B | 0.9800 |
C3—H3B | 0.9800 | C35—H35C | 0.9800 |
C3—H3C | 0.9800 | O9'—O9'i | 1.42 (3) |
C4—C5 | 1.393 (3) | O9'—C35' | 1.473 (15) |
C4—C9 | 1.398 (3) | O9'—H9'A | 0.8500 |
C5—C6 | 1.382 (4) | C35'—H9A | 1.2583 |
C5—H5A | 0.9500 | C35'—H35D | 0.9800 |
C6—C7 | 1.398 (4) | C35'—H35E | 0.9800 |
C6—H6A | 0.9500 | C35'—H35F | 0.9800 |
C7—C8 | 1.389 (4) | O7—C33 | 1.221 (4) |
C7—H7A | 0.9500 | N10—C33 | 1.320 (4) |
C8—C9 | 1.393 (3) | N10—C32 | 1.439 (4) |
C8—H8A | 0.9500 | N10—C31 | 1.4743 |
C10—C11 | 1.497 (3) | C31—H31A | 0.9800 |
C10—H10A | 0.9900 | C31—H31B | 0.9800 |
C10—H10B | 0.9900 | C31—H31C | 0.9800 |
C12—H12A | 0.9800 | C32—H32A | 0.9800 |
C12—H12B | 0.9800 | C32—H32B | 0.9800 |
C12—H12C | 0.9800 | C32—H32C | 0.9800 |
C13—C14 | 1.391 (3) | C33—H33A | 0.9500 |
C13—C18 | 1.406 (3) | O8—C34 | 1.396 (4) |
C14—C15 | 1.383 (4) | O8—H8O | 0.8399 |
C14—H14A | 0.9500 | C34—H34A | 0.9800 |
C15—C16 | 1.413 (4) | C34—H34B | 0.9800 |
C15—H15A | 0.9500 | C34—H34C | 0.9800 |
C16—C17 | 1.385 (4) | Cl—O3 | 1.417 (3) |
C16—H16A | 0.9500 | Cl—O4 | 1.426 (2) |
C17—C18 | 1.391 (3) | Cl—O6 | 1.440 (2) |
C17—H17A | 0.9500 | Cl—O5 | 1.441 (2) |
O1—Zn—O1' | 40.2 (3) | C16—C17—H17A | 121.2 |
O1—Zn—N3 | 109.73 (9) | C18—C17—H17A | 121.2 |
O1'—Zn—N3 | 99.7 (4) | C17—C18—N3 | 131.3 (2) |
O1—Zn—N1 | 91.83 (8) | C17—C18—C13 | 120.4 (2) |
O1'—Zn—N1 | 129.8 (3) | N3—C18—C13 | 108.3 (2) |
N3—Zn—N1 | 113.36 (7) | N7—C19—C20 | 107.57 (19) |
O1—Zn—N5 | 114.45 (9) | N7—C19—H19A | 110.2 |
O1'—Zn—N5 | 85.6 (2) | C20—C19—H19A | 110.2 |
N3—Zn—N5 | 113.95 (8) | N7—C19—H19B | 110.2 |
N1—Zn—N5 | 111.62 (8) | C20—C19—H19B | 110.2 |
O1—Zn—N7 | 165.85 (8) | H19A—C19—H19B | 108.5 |
O1'—Zn—N7 | 153.8 (2) | N5—C20—N6 | 112.6 (2) |
N3—Zn—N7 | 74.52 (7) | N5—C20—C19 | 122.9 (2) |
N1—Zn—N7 | 74.26 (7) | N6—C20—C19 | 124.6 (2) |
N5—Zn—N7 | 74.16 (7) | N6—C21—H21A | 109.5 |
C2—N1—C9 | 105.68 (19) | N6—C21—H21B | 109.5 |
C2—N1—Zn | 118.50 (15) | H21A—C21—H21B | 109.5 |
C9—N1—Zn | 135.45 (16) | N6—C21—H21C | 109.5 |
C2—N2—C4 | 107.03 (19) | H21A—C21—H21C | 109.5 |
C2—N2—C3 | 127.3 (2) | H21B—C21—H21C | 109.5 |
C4—N2—C3 | 125.6 (2) | C23—C22—N6 | 131.5 (2) |
C11—N3—C18 | 105.37 (19) | C23—C22—C27 | 122.5 (3) |
C11—N3—Zn | 118.12 (15) | N6—C22—C27 | 105.9 (2) |
C18—N3—Zn | 135.63 (16) | C24—C23—C22 | 116.6 (3) |
C11—N4—C13 | 107.08 (19) | C24—C23—H23A | 121.7 |
C11—N4—C12 | 126.3 (2) | C22—C23—H23A | 121.7 |
C13—N4—C12 | 126.6 (2) | C23—C24—C25 | 122.0 (3) |
C20—N5—C27 | 105.7 (2) | C23—C24—H24A | 119.0 |
C20—N5—Zn | 118.67 (16) | C25—C24—H24A | 119.0 |
C27—N5—Zn | 135.45 (16) | C24—C25—C26 | 121.2 (3) |
C20—N6—C22 | 107.2 (2) | C24—C25—H25A | 119.4 |
C20—N6—C21 | 127.6 (2) | C26—C25—H25A | 119.4 |
C22—N6—C21 | 125.2 (2) | C27—C26—C25 | 117.5 (3) |
C19—N7—C1 | 113.95 (19) | C27—C26—H26A | 121.2 |
C19—N7—C10 | 112.14 (19) | C25—C26—H26A | 121.2 |
C1—N7—C10 | 113.24 (18) | C26—C27—N5 | 131.4 (2) |
C19—N7—Zn | 106.35 (13) | C26—C27—C22 | 120.0 (2) |
C1—N7—Zn | 104.88 (13) | N5—C27—C22 | 108.6 (2) |
C10—N7—Zn | 105.36 (13) | O1—C28—O2 | 122.3 (2) |
N7—C1—C2 | 108.60 (18) | O1—C28—C29 | 119.2 (2) |
N7—C1—H1A | 110.0 | O2—C28—C29 | 118.3 (2) |
C2—C1—H1A | 110.0 | C28—O1—Zn | 122.54 (18) |
N7—C1—H1B | 110.0 | C30—C29—C28 | 125.5 (3) |
C2—C1—H1B | 110.0 | C30—C29—H29 | 117.3 |
H1A—C1—H1B | 108.4 | C28—C29—H29 | 117.3 |
N1—C2—N2 | 112.7 (2) | C29—C30—H30A | 120.0 |
N1—C2—C1 | 122.6 (2) | C29—C30—H30B | 120.0 |
N2—C2—C1 | 124.7 (2) | H30A—C30—H30B | 120.0 |
N2—C3—H3A | 109.5 | C35—O9—H9A | 96.7 |
N2—C3—H3B | 109.5 | O9—C35—H35A | 109.5 |
H3A—C3—H3B | 109.5 | O9—C35—H35B | 109.5 |
N2—C3—H3C | 109.5 | H35A—C35—H35B | 109.5 |
H3A—C3—H3C | 109.5 | O9—C35—H35C | 109.5 |
H3B—C3—H3C | 109.5 | H35A—C35—H35C | 109.5 |
N2—C4—C5 | 131.8 (2) | H35B—C35—H35C | 109.5 |
N2—C4—C9 | 105.9 (2) | O9'i—O9'—C35' | 88.2 (14) |
C5—C4—C9 | 122.3 (2) | O9'i—O9'—H9'A | 139.6 |
C6—C5—C4 | 116.5 (2) | C35'—O9'—H9'A | 111.3 |
C6—C5—H5A | 121.8 | O9'—C35'—H9A | 86.6 |
C4—C5—H5A | 121.8 | O9'—C35'—H35D | 109.5 |
C5—C6—C7 | 121.8 (2) | H9A—C35'—H35D | 74.3 |
C5—C6—H6A | 119.1 | O9'—C35'—H35E | 109.5 |
C7—C6—H6A | 119.1 | H9A—C35'—H35E | 52.4 |
C8—C7—C6 | 121.6 (2) | H35D—C35'—H35E | 109.5 |
C8—C7—H7A | 119.2 | O9'—C35'—H35F | 109.5 |
C6—C7—H7A | 119.2 | H9A—C35'—H35F | 160.1 |
C7—C8—C9 | 117.1 (2) | H35D—C35'—H35F | 109.5 |
C7—C8—H8A | 121.4 | H35E—C35'—H35F | 109.5 |
C9—C8—H8A | 121.4 | C33—N10—C32 | 121.9 (3) |
C8—C9—N1 | 130.6 (2) | C33—N10—C31 | 121.23 (17) |
C8—C9—C4 | 120.7 (2) | C32—N10—C31 | 116.8 (2) |
N1—C9—C4 | 108.7 (2) | N10—C31—H31A | 109.5 |
N7—C10—C11 | 108.52 (18) | N10—C31—H31B | 109.5 |
N7—C10—H10A | 110.0 | H31A—C31—H31B | 109.5 |
C11—C10—H10A | 110.0 | N10—C31—H31C | 109.5 |
N7—C10—H10B | 110.0 | H31A—C31—H31C | 109.5 |
C11—C10—H10B | 110.0 | H31B—C31—H31C | 109.5 |
H10A—C10—H10B | 108.4 | N10—C32—H32A | 109.5 |
N3—C11—N4 | 113.1 (2) | N10—C32—H32B | 109.5 |
N3—C11—C10 | 123.4 (2) | H32A—C32—H32B | 109.5 |
N4—C11—C10 | 123.4 (2) | N10—C32—H32C | 109.5 |
N4—C12—H12A | 109.5 | H32A—C32—H32C | 109.5 |
N4—C12—H12B | 109.5 | H32B—C32—H32C | 109.5 |
H12A—C12—H12B | 109.5 | O7—C33—N10 | 125.6 (3) |
N4—C12—H12C | 109.5 | O7—C33—H33A | 117.2 |
H12A—C12—H12C | 109.5 | N10—C33—H33A | 117.2 |
H12B—C12—H12C | 109.5 | C34—O8—H8O | 102.5 |
N4—C13—C14 | 131.4 (2) | O8—C34—H34A | 109.5 |
N4—C13—C18 | 106.1 (2) | O8—C34—H34B | 109.5 |
C14—C13—C18 | 122.5 (2) | H34A—C34—H34B | 109.5 |
C15—C14—C13 | 116.5 (2) | O8—C34—H34C | 109.5 |
C15—C14—H14A | 121.7 | H34A—C34—H34C | 109.5 |
C13—C14—H14A | 121.7 | H34B—C34—H34C | 109.5 |
C14—C15—C16 | 121.6 (2) | O3—Cl—O4 | 110.16 (19) |
C14—C15—H15A | 119.2 | O3—Cl—O6 | 109.73 (16) |
C16—C15—H15A | 119.2 | O4—Cl—O6 | 111.24 (17) |
C17—C16—C15 | 121.3 (2) | O3—Cl—O5 | 108.9 (2) |
C17—C16—H16A | 119.3 | O4—Cl—O5 | 108.55 (16) |
C15—C16—H16A | 119.3 | O6—Cl—O5 | 108.25 (14) |
C16—C17—C18 | 117.6 (2) |
Symmetry code: (i) −x−1, −y−1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O8—H8O···O7ii | 0.84 | 1.93 | 2.768 (3) | 180 |
Symmetry code: (ii) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C3H3O2)(C27H27N7)](ClO4)·C3H7NO·1.5CH4O |
Mr | 806.61 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 153 |
a, b, c (Å) | 11.3766 (4), 13.9606 (4), 14.4355 (5) |
α, β, γ (°) | 108.579 (1), 111.011 (1), 100.075 (1) |
V (Å3) | 1917.33 (11) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.77 |
Crystal size (mm) | 0.59 × 0.56 × 0.40 |
Data collection | |
Diffractometer | Rigaku R-axis SPIDER diffractometer |
Absorption correction | Multi-scan (Higashi; 1995) |
Tmin, Tmax | 0.659, 0.748 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18907, 8711, 7735 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.144, 1.05 |
No. of reflections | 8711 |
No. of parameters | 523 |
No. of restraints | 28 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.29, −0.74 |
Computer programs: RAPID-AUTO (Rigaku/MSC 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003), SHELXTL (Bruker, 1997).
Zn—O1 | 1.988 (2) | Zn—N5 | 2.071 (2) |
Zn—N3 | 2.0433 (19) | Zn—N7 | 2.4497 (19) |
Zn—N1 | 2.0564 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O8—H8O···O7i | 0.84 | 1.93 | 2.768 (3) | 179.9 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Acknowledgements
The authors acknowledge the financial support and grant from the Qing Lan Talent Engineering Funds (QL-05–03 A) by Lanzhou Jiaotong University. A grant from the Middle-Young Age Science Foundation of Gansu Province (grant No. 3YS061-A25–023,24) is also acknowledged.
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (1997). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). RAPID-AUTO. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Youngme, 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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The asymmetric unit of the title compound consists of a discrete [Zn(Mentb)(acrylate)] cation (Fig. 1), a perchlorate anion, a DMF molecule and 1.5 molecules of methanol. The zinc ion is five-coordinated with a N4O ligand set. The Mentb ligand acts as a tetradentate N-donor, and an O atom of a carboxylate group of the acrylate ligand completes the coordination. The coordination geometry of the ZnII may be best described as distorted trigonal bipyramid (τ = 0.85), with approximate site symmetry C3. The parameter τ is defined as (β - α)/60 [where β = O1—Zn—N7, α = O1—Zn—N5] and its value varies from 0 (in regular square-based pyramidal) to 1 (in regular trigonal bipyramidal) [Youngme et al., 2007]. This geometry is assumed by the ZnII ion to relieve the steric crowding. The equatorial plane is occupied by three N atoms of three benzimidazolyl groups, while the ZnII ion protrudes towards O1 by 0.558 (8) Å from the plane of atoms N1/N3/N5. The axial positions are occupyied by N7 and O1. The three benzimidazole ring arms of the Mentb ligand form a cone-shaped cavity. The distance between ZnII and O2 is 3.068 (2) Å, so O2 is not considered coordinated. The distances within the ligands are normal [Allen et al., 1987]. The crystal structure is stabilized by weak intermolecular O—H···O hydrogen bonds and weak π···π stacking interactions with Cg1···Cg2i = 3.465 (2)Å [symmetry code: (i) 1 - x, 1 - y, 1 - z] and a perpendicular distance of 3.437 Å, where Cg1 and Cg2 are the centroids defined by atoms C4—C9 and N1/C2/N2/C4/C9 respectively.