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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): m316.
Published online 2008 January 9. doi:  10.1107/S1600536807068675
PMCID: PMC2960207

Acrylato[tris­(1-methyl­benzimidazol-2-ylmeth­yl)amine]zinc(II) perchlorate–dimethyl­formamide–methanol (1/1/1.5) at 153 (2) K

Abstract

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 C 3 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 crystal structure, 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 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m316-scheme1.jpg

Experimental

Crystal data

  • [Zn(C3H3O2)(C27H27N7)](ClO4)·C3H7NO·1.5CH4O
  • M r = 806.61
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m316-efi1.jpg
  • a = 11.3766 (4) Å
  • b = 13.9606 (4) Å
  • c = 14.4355 (5) Å
  • α = 108.579 (1)°
  • β = 111.011 (1)°
  • γ = 100.075 (1)°
  • V = 1917.33 (11) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.77 mm−1
  • T = 153 (2) K
  • 0.59 × 0.56 × 0.40 mm

Data collection

  • Rigaku R-AXIS SPIDER diffractometer
  • Absorption correction: multi-scan (Higashi; 1995 [triangle]) T min = 0.659, T max = 0.748
  • 18907 measured reflections
  • 8711 independent reflections
  • 7735 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.144
  • S = 1.05
  • 8711 reflections
  • 523 parameters
  • 28 restraints
  • H-atom parameters constrained
  • Δρmax = 1.29 e Å−3
  • Δρmin = −0.73 e Å−3

Data collection: RAPID-AUTO (Rigaku/MSC 2004 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Bruker, 1997 [triangle]) and PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807068675/lh2580sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068675/lh2580Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

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.

Experimental

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)

Refinement

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).

Figures

Fig. 1.
The molecular structure of the cation of the title compound. Hydrogen atoms have been omitted and the displacement ellipsoids are shown at the 30% probability level. The disorder is not shown.
Fig. 2.
The Packing of the title compound. H atoms are omitted for clarity. The donor-acceptor distances of hydrogen bonds are shown as dashed lines. The disorder is not shown.

Crystal data

[Zn(C3H3O2)(C27H27N7)](ClO4)·C3H7NO·1.5CH4OZ = 2
Mr = 806.61F000 = 842
Triclinic, P1Dx = 1.397 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 11.3766 (4) ÅCell parameters from 16325 reflections
b = 13.9606 (4) Åθ = 3.0–27.5º
c = 14.4355 (5) ŵ = 0.77 mm1
α = 108.579 (1)ºT = 153 (2) K
β = 111.011 (1)ºBlock, colorless
γ = 100.075 (1)º0.59 × 0.56 × 0.40 mm
V = 1917.33 (11) Å3

Data collection

Rigaku R-axis SPIDER diffractometer8711 independent reflections
Radiation source: Rotating Anode7735 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.024
T = 153(2) Kθmax = 27.5º
ω scansθmin = 3.0º
Absorption correction: multi-scan(Higashi; 1995)h = −14→14
Tmin = 0.659, Tmax = 0.748k = −18→17
18907 measured reflectionsl = −18→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.144  w = 1/[σ2(Fo2) + (0.088P)2 + 1.5221P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
8711 reflectionsΔρmax = 1.29 e Å3
523 parametersΔρmin = −0.73 e Å3
28 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

xyzUiso*/UeqOcc. (<1)
Zn0.35354 (2)0.15960 (2)0.32037 (2)0.02210 (10)
N10.43780 (19)0.29536 (15)0.46350 (16)0.0226 (4)
N20.4269 (2)0.41504 (16)0.60253 (17)0.0259 (4)
N30.16855 (19)0.14640 (15)0.21459 (15)0.0230 (4)
N4−0.05296 (19)0.08379 (15)0.14418 (16)0.0249 (4)
N50.3625 (2)0.02424 (16)0.34902 (16)0.0250 (4)
N60.3172 (2)−0.08938 (17)0.42042 (17)0.0288 (4)
N70.21188 (19)0.14020 (15)0.41159 (16)0.0233 (4)
C10.2265 (2)0.24986 (19)0.4776 (2)0.0262 (5)
H1A0.21020.25240.54110.031*
H1B0.16090.27510.43350.031*
C20.3647 (2)0.31989 (18)0.51553 (19)0.0235 (4)
C30.3742 (3)0.4680 (2)0.6758 (2)0.0363 (6)
H3A0.27680.44430.63690.054*
H3B0.40980.54560.70100.054*
H3C0.40070.44960.73870.054*
C40.5506 (2)0.45659 (19)0.6080 (2)0.0258 (5)
C50.6552 (3)0.5515 (2)0.6807 (2)0.0337 (5)
H5A0.65030.60260.74000.040*
C60.7666 (3)0.5675 (2)0.6621 (2)0.0371 (6)
H6A0.84050.63090.71030.045*
C70.7735 (3)0.4929 (2)0.5744 (2)0.0357 (6)
H7A0.85160.50720.56410.043*
C80.6690 (2)0.3983 (2)0.5020 (2)0.0282 (5)
H8A0.67400.34750.44260.034*
C90.5564 (2)0.38108 (18)0.52022 (19)0.0238 (4)
C100.0769 (2)0.07969 (19)0.32346 (19)0.0254 (5)
H10A0.01040.09980.34800.030*
H10B0.06030.00210.30280.030*
C110.0646 (2)0.10465 (17)0.22763 (19)0.0230 (4)
C12−0.1853 (2)0.0394 (2)0.1352 (2)0.0323 (5)
H12A−0.1830−0.01240.16780.048*
H12B−0.25020.00360.05810.048*
H12C−0.21110.09730.17350.048*
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−0.20280.0845−0.05870.036*
C15−0.0471 (3)0.1523 (2)−0.0823 (2)0.0338 (5)
H15A−0.10050.1523−0.15010.041*
C160.0931 (3)0.1928 (2)−0.0383 (2)0.0335 (5)
H16A0.13180.2195−0.07720.040*
C170.1751 (3)0.19458 (19)0.06038 (19)0.0279 (5)
H17A0.26930.22170.08970.033*
C180.1145 (2)0.15516 (18)0.11509 (18)0.0241 (4)
C190.2620 (2)0.0809 (2)0.4757 (2)0.0274 (5)
H19A0.18950.04090.48520.033*
H19B0.33400.13070.54870.033*
C200.3142 (2)0.0051 (2)0.41521 (19)0.0259 (5)
C210.2753 (3)−0.1350 (2)0.4862 (2)0.0375 (6)
H21A0.2256−0.09410.51590.056*
H21B0.3540−0.13190.54620.056*
H21C0.2182−0.20970.44050.056*
C220.3701 (2)−0.1366 (2)0.3518 (2)0.0290 (5)
C230.3908 (3)−0.2346 (2)0.3233 (2)0.0381 (6)
H23A0.3668−0.28420.35100.046*
C240.4480 (3)−0.2564 (2)0.2530 (2)0.0438 (7)
H24A0.4641−0.32270.23190.053*
C250.4830 (3)−0.1842 (2)0.2118 (2)0.0417 (7)
H25A0.5244−0.20150.16500.050*
C260.4583 (3)−0.0871 (2)0.2381 (2)0.0332 (5)
H26A0.4804−0.03850.20870.040*
C270.4004 (2)−0.06388 (19)0.30861 (19)0.0266 (5)
C280.4818 (2)0.1641 (2)0.18395 (19)0.0314 (5)
O10.4880 (2)0.21199 (19)0.27462 (17)0.0352 (6)0.836 (5)
O20.4042 (2)0.06708 (18)0.12040 (18)0.0360 (6)0.836 (5)
C290.5724 (3)0.2162 (3)0.1495 (3)0.0322 (7)0.836 (5)
H290.63600.28430.20080.039*0.836 (5)
C300.5724 (4)0.1770 (3)0.0555 (3)0.0584 (9)
H30A0.51040.10920.00190.070*0.836 (5)
H30B0.63440.21610.04000.070*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)
H29'0.51870.04890.07450.084*0.164 (5)
H30C0.58090.25070.07780.070*0.164 (5)
H30D0.59830.14360.00110.070*0.164 (5)
O9−0.3164 (15)−0.4481 (12)−0.0180 (13)0.097 (4)0.25
H9A−0.3562−0.4937−0.08410.145*0.25
C35−0.404 (3)−0.498 (2)0.020 (2)0.108 (6)0.25
H35A−0.3769−0.45340.09660.161*0.25
H35B−0.3972−0.56910.01210.161*0.25
H35C−0.4964−0.5054−0.02420.161*0.25
O9'−0.4896 (14)−0.5339 (13)−0.0429 (14)0.098 (4)0.25
H9'A−0.5219−0.5595−0.11200.147*0.25
C35'−0.3528 (2)−0.45924 (15)0.00898 (18)0.108 (6)0.25
H35D−0.3532−0.3997−0.01300.161*0.25
H35E−0.2961−0.4968−0.01400.161*0.25
H35F−0.3180−0.43160.08840.161*0.25
O71.1335 (2)0.55543 (15)0.72271 (18)0.0648 (7)
N101.0423 (2)0.51106 (15)0.82520 (18)0.0563 (7)
C310.9669 (2)0.42510 (15)0.84068 (18)0.100 (2)
H31A0.94860.35580.78330.150*
H31B0.88270.43570.83680.150*
H31C1.01950.42680.91220.150*
C321.0725 (5)0.6191 (3)0.8999 (4)0.0653 (10)
H32A1.12060.66900.88060.098*
H32B1.12810.62910.97430.098*
H32C0.98950.63280.89550.098*
C331.0770 (4)0.4894 (3)0.7448 (3)0.0534 (8)
H33A1.05630.41620.70030.064*
O8−0.0521 (2)0.28742 (17)0.33417 (18)0.0412 (5)
H8O−0.07670.33510.31690.062*
C34−0.1037 (4)0.2828 (4)0.4076 (4)0.0650 (11)
H34A−0.07330.23370.43880.097*
H34B−0.20130.25720.36930.097*
H34C−0.07280.35430.46610.097*
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)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn0.02388 (15)0.02273 (15)0.02353 (15)0.00978 (10)0.01317 (11)0.01000 (11)
N10.0230 (9)0.0219 (9)0.0252 (9)0.0086 (7)0.0122 (8)0.0103 (8)
N20.0308 (10)0.0231 (10)0.0286 (10)0.0124 (8)0.0160 (8)0.0113 (8)
N30.0266 (9)0.0198 (9)0.0219 (9)0.0067 (7)0.0115 (8)0.0076 (7)
N40.0239 (9)0.0212 (9)0.0255 (9)0.0068 (7)0.0087 (8)0.0076 (8)
N50.0283 (10)0.0239 (9)0.0265 (9)0.0112 (8)0.0136 (8)0.0117 (8)
N60.0297 (10)0.0309 (11)0.0319 (10)0.0132 (8)0.0130 (9)0.0192 (9)
N70.0231 (9)0.0233 (9)0.0239 (9)0.0083 (7)0.0110 (8)0.0094 (8)
C10.0280 (11)0.0257 (11)0.0296 (11)0.0105 (9)0.0179 (10)0.0101 (9)
C20.0253 (11)0.0244 (11)0.0248 (10)0.0111 (9)0.0127 (9)0.0114 (9)
C30.0470 (15)0.0295 (13)0.0374 (14)0.0153 (11)0.0273 (13)0.0086 (11)
C40.0283 (11)0.0226 (11)0.0312 (12)0.0109 (9)0.0137 (10)0.0151 (9)
C50.0409 (14)0.0198 (11)0.0373 (13)0.0093 (10)0.0159 (12)0.0102 (10)
C60.0340 (13)0.0223 (12)0.0452 (15)0.0015 (10)0.0127 (12)0.0120 (11)
C70.0305 (13)0.0283 (13)0.0507 (16)0.0069 (10)0.0186 (12)0.0201 (12)
C80.0277 (11)0.0246 (11)0.0380 (13)0.0109 (9)0.0165 (10)0.0163 (10)
C90.0249 (11)0.0217 (11)0.0297 (11)0.0107 (8)0.0115 (9)0.0158 (9)
C100.0232 (11)0.0256 (11)0.0281 (11)0.0068 (9)0.0118 (9)0.0123 (9)
C110.0246 (11)0.0177 (10)0.0249 (10)0.0073 (8)0.0105 (9)0.0070 (8)
C120.0242 (11)0.0331 (13)0.0358 (13)0.0075 (9)0.0120 (10)0.0125 (11)
C130.0282 (11)0.0161 (10)0.0258 (11)0.0067 (8)0.0106 (9)0.0054 (8)
C140.0316 (12)0.0240 (11)0.0268 (11)0.0098 (9)0.0072 (10)0.0066 (9)
C150.0433 (14)0.0298 (13)0.0242 (11)0.0138 (11)0.0109 (11)0.0098 (10)
C160.0443 (15)0.0304 (13)0.0280 (12)0.0122 (11)0.0178 (11)0.0127 (10)
C170.0338 (12)0.0235 (11)0.0245 (11)0.0090 (9)0.0127 (10)0.0084 (9)
C180.0288 (11)0.0188 (10)0.0218 (10)0.0086 (8)0.0096 (9)0.0062 (8)
C190.0314 (12)0.0311 (12)0.0270 (11)0.0139 (10)0.0164 (10)0.0151 (10)
C200.0243 (11)0.0298 (12)0.0258 (11)0.0112 (9)0.0092 (9)0.0152 (9)
C210.0387 (14)0.0441 (15)0.0445 (15)0.0166 (12)0.0200 (12)0.0328 (13)
C220.0271 (12)0.0303 (12)0.0280 (12)0.0129 (9)0.0072 (10)0.0143 (10)
C230.0460 (15)0.0334 (14)0.0358 (14)0.0202 (12)0.0112 (12)0.0195 (11)
C240.0578 (18)0.0359 (15)0.0364 (14)0.0306 (14)0.0127 (14)0.0147 (12)
C250.0546 (18)0.0435 (16)0.0324 (13)0.0323 (14)0.0191 (13)0.0140 (12)
C260.0417 (14)0.0348 (14)0.0301 (12)0.0221 (11)0.0176 (11)0.0149 (11)
C270.0268 (11)0.0266 (11)0.0253 (11)0.0128 (9)0.0081 (9)0.0113 (9)
C280.0234 (11)0.0411 (15)0.0286 (12)0.0079 (10)0.0108 (10)0.0153 (11)
O10.0306 (11)0.0413 (14)0.0298 (11)0.0043 (9)0.0180 (9)0.0088 (10)
O20.0367 (12)0.0289 (11)0.0314 (12)0.0018 (9)0.0102 (10)0.0095 (9)
C290.0296 (15)0.0387 (17)0.0360 (16)0.0113 (13)0.0201 (13)0.0182 (14)
C300.060 (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)
O90.106 (6)0.085 (6)0.089 (6)0.002 (4)0.036 (4)0.048 (5)
C350.105 (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)
O70.0665 (16)0.0675 (17)0.101 (2)0.0383 (14)0.0541 (16)0.0547 (17)
N100.0695 (19)0.0356 (14)0.0688 (19)0.0159 (13)0.0407 (17)0.0167 (13)
C310.152 (5)0.049 (2)0.122 (4)0.015 (3)0.102 (4)0.024 (3)
C320.078 (3)0.0409 (19)0.069 (2)0.0217 (18)0.034 (2)0.0109 (17)
C330.062 (2)0.0419 (17)0.068 (2)0.0253 (15)0.0372 (19)0.0233 (16)
O80.0394 (11)0.0405 (11)0.0539 (12)0.0173 (9)0.0283 (10)0.0206 (10)
C340.069 (2)0.093 (3)0.080 (3)0.052 (2)0.055 (2)0.052 (2)
Cl0.0412 (4)0.0373 (3)0.0420 (4)0.0115 (3)0.0224 (3)0.0240 (3)
O30.0457 (14)0.100 (2)0.134 (3)0.0352 (15)0.0412 (17)0.092 (2)
O40.092 (2)0.0420 (14)0.0653 (17)−0.0064 (13)0.0423 (16)0.0146 (12)
O50.0525 (14)0.0726 (17)0.0428 (12)0.0167 (12)0.0285 (11)0.0151 (12)
O60.0566 (13)0.0657 (15)0.0430 (11)0.0255 (11)0.0333 (11)0.0290 (11)

Geometric parameters (Å, °)

Zn—O11.988 (2)C19—C201.495 (3)
Zn—O1'2.021 (7)C19—H19A0.9900
Zn—N32.0433 (19)C19—H19B0.9900
Zn—N12.0564 (19)C21—H21A0.9800
Zn—N52.071 (2)C21—H21B0.9800
Zn—N72.4497 (19)C21—H21C0.9800
N1—C21.326 (3)C22—C231.386 (4)
N1—C91.393 (3)C22—C271.405 (3)
N2—C21.347 (3)C23—C241.376 (4)
N2—C41.389 (3)C23—H23A0.9500
N2—C31.462 (3)C24—C251.392 (5)
N3—C111.328 (3)C24—H24A0.9500
N3—C181.400 (3)C25—C261.394 (4)
N4—C111.345 (3)C25—H25A0.9500
N4—C131.385 (3)C26—C271.386 (4)
N4—C121.466 (3)C26—H26A0.9500
N5—C201.332 (3)C28—O11.235 (3)
N5—C271.396 (3)C28—O21.290 (3)
N6—C201.351 (3)C28—C291.474 (4)
N6—C221.388 (3)C29—C301.292 (5)
N6—C211.463 (3)C29—H290.9500
N7—C191.464 (3)C30—H30A0.9500
N7—C11.465 (3)C30—H30B0.9500
N7—C101.466 (3)C29'—H29'0.9500
C1—C21.493 (3)O9—C351.473 (15)
C1—H1A0.9900O9—H9A0.8500
C1—H1B0.9900C35—H35A0.9800
C3—H3A0.9800C35—H35B0.9800
C3—H3B0.9800C35—H35C0.9800
C3—H3C0.9800O9'—O9'i1.42 (3)
C4—C51.393 (3)O9'—C35'1.473 (15)
C4—C91.398 (3)O9'—H9'A0.8500
C5—C61.382 (4)C35'—H9A1.2583
C5—H5A0.9500C35'—H35D0.9800
C6—C71.398 (4)C35'—H35E0.9800
C6—H6A0.9500C35'—H35F0.9800
C7—C81.389 (4)O7—C331.221 (4)
C7—H7A0.9500N10—C331.320 (4)
C8—C91.393 (3)N10—C321.439 (4)
C8—H8A0.9500N10—C311.4743
C10—C111.497 (3)C31—H31A0.9800
C10—H10A0.9900C31—H31B0.9800
C10—H10B0.9900C31—H31C0.9800
C12—H12A0.9800C32—H32A0.9800
C12—H12B0.9800C32—H32B0.9800
C12—H12C0.9800C32—H32C0.9800
C13—C141.391 (3)C33—H33A0.9500
C13—C181.406 (3)O8—C341.396 (4)
C14—C151.383 (4)O8—H8O0.8399
C14—H14A0.9500C34—H34A0.9800
C15—C161.413 (4)C34—H34B0.9800
C15—H15A0.9500C34—H34C0.9800
C16—C171.385 (4)Cl—O31.417 (3)
C16—H16A0.9500Cl—O41.426 (2)
C17—C181.391 (3)Cl—O61.440 (2)
C17—H17A0.9500Cl—O51.441 (2)
O1—Zn—O1'40.2 (3)C16—C17—H17A121.2
O1—Zn—N3109.73 (9)C18—C17—H17A121.2
O1'—Zn—N399.7 (4)C17—C18—N3131.3 (2)
O1—Zn—N191.83 (8)C17—C18—C13120.4 (2)
O1'—Zn—N1129.8 (3)N3—C18—C13108.3 (2)
N3—Zn—N1113.36 (7)N7—C19—C20107.57 (19)
O1—Zn—N5114.45 (9)N7—C19—H19A110.2
O1'—Zn—N585.6 (2)C20—C19—H19A110.2
N3—Zn—N5113.95 (8)N7—C19—H19B110.2
N1—Zn—N5111.62 (8)C20—C19—H19B110.2
O1—Zn—N7165.85 (8)H19A—C19—H19B108.5
O1'—Zn—N7153.8 (2)N5—C20—N6112.6 (2)
N3—Zn—N774.52 (7)N5—C20—C19122.9 (2)
N1—Zn—N774.26 (7)N6—C20—C19124.6 (2)
N5—Zn—N774.16 (7)N6—C21—H21A109.5
C2—N1—C9105.68 (19)N6—C21—H21B109.5
C2—N1—Zn118.50 (15)H21A—C21—H21B109.5
C9—N1—Zn135.45 (16)N6—C21—H21C109.5
C2—N2—C4107.03 (19)H21A—C21—H21C109.5
C2—N2—C3127.3 (2)H21B—C21—H21C109.5
C4—N2—C3125.6 (2)C23—C22—N6131.5 (2)
C11—N3—C18105.37 (19)C23—C22—C27122.5 (3)
C11—N3—Zn118.12 (15)N6—C22—C27105.9 (2)
C18—N3—Zn135.63 (16)C24—C23—C22116.6 (3)
C11—N4—C13107.08 (19)C24—C23—H23A121.7
C11—N4—C12126.3 (2)C22—C23—H23A121.7
C13—N4—C12126.6 (2)C23—C24—C25122.0 (3)
C20—N5—C27105.7 (2)C23—C24—H24A119.0
C20—N5—Zn118.67 (16)C25—C24—H24A119.0
C27—N5—Zn135.45 (16)C24—C25—C26121.2 (3)
C20—N6—C22107.2 (2)C24—C25—H25A119.4
C20—N6—C21127.6 (2)C26—C25—H25A119.4
C22—N6—C21125.2 (2)C27—C26—C25117.5 (3)
C19—N7—C1113.95 (19)C27—C26—H26A121.2
C19—N7—C10112.14 (19)C25—C26—H26A121.2
C1—N7—C10113.24 (18)C26—C27—N5131.4 (2)
C19—N7—Zn106.35 (13)C26—C27—C22120.0 (2)
C1—N7—Zn104.88 (13)N5—C27—C22108.6 (2)
C10—N7—Zn105.36 (13)O1—C28—O2122.3 (2)
N7—C1—C2108.60 (18)O1—C28—C29119.2 (2)
N7—C1—H1A110.0O2—C28—C29118.3 (2)
C2—C1—H1A110.0C28—O1—Zn122.54 (18)
N7—C1—H1B110.0C30—C29—C28125.5 (3)
C2—C1—H1B110.0C30—C29—H29117.3
H1A—C1—H1B108.4C28—C29—H29117.3
N1—C2—N2112.7 (2)C29—C30—H30A120.0
N1—C2—C1122.6 (2)C29—C30—H30B120.0
N2—C2—C1124.7 (2)H30A—C30—H30B120.0
N2—C3—H3A109.5C35—O9—H9A96.7
N2—C3—H3B109.5O9—C35—H35A109.5
H3A—C3—H3B109.5O9—C35—H35B109.5
N2—C3—H3C109.5H35A—C35—H35B109.5
H3A—C3—H3C109.5O9—C35—H35C109.5
H3B—C3—H3C109.5H35A—C35—H35C109.5
N2—C4—C5131.8 (2)H35B—C35—H35C109.5
N2—C4—C9105.9 (2)O9'i—O9'—C35'88.2 (14)
C5—C4—C9122.3 (2)O9'i—O9'—H9'A139.6
C6—C5—C4116.5 (2)C35'—O9'—H9'A111.3
C6—C5—H5A121.8O9'—C35'—H9A86.6
C4—C5—H5A121.8O9'—C35'—H35D109.5
C5—C6—C7121.8 (2)H9A—C35'—H35D74.3
C5—C6—H6A119.1O9'—C35'—H35E109.5
C7—C6—H6A119.1H9A—C35'—H35E52.4
C8—C7—C6121.6 (2)H35D—C35'—H35E109.5
C8—C7—H7A119.2O9'—C35'—H35F109.5
C6—C7—H7A119.2H9A—C35'—H35F160.1
C7—C8—C9117.1 (2)H35D—C35'—H35F109.5
C7—C8—H8A121.4H35E—C35'—H35F109.5
C9—C8—H8A121.4C33—N10—C32121.9 (3)
C8—C9—N1130.6 (2)C33—N10—C31121.23 (17)
C8—C9—C4120.7 (2)C32—N10—C31116.8 (2)
N1—C9—C4108.7 (2)N10—C31—H31A109.5
N7—C10—C11108.52 (18)N10—C31—H31B109.5
N7—C10—H10A110.0H31A—C31—H31B109.5
C11—C10—H10A110.0N10—C31—H31C109.5
N7—C10—H10B110.0H31A—C31—H31C109.5
C11—C10—H10B110.0H31B—C31—H31C109.5
H10A—C10—H10B108.4N10—C32—H32A109.5
N3—C11—N4113.1 (2)N10—C32—H32B109.5
N3—C11—C10123.4 (2)H32A—C32—H32B109.5
N4—C11—C10123.4 (2)N10—C32—H32C109.5
N4—C12—H12A109.5H32A—C32—H32C109.5
N4—C12—H12B109.5H32B—C32—H32C109.5
H12A—C12—H12B109.5O7—C33—N10125.6 (3)
N4—C12—H12C109.5O7—C33—H33A117.2
H12A—C12—H12C109.5N10—C33—H33A117.2
H12B—C12—H12C109.5C34—O8—H8O102.5
N4—C13—C14131.4 (2)O8—C34—H34A109.5
N4—C13—C18106.1 (2)O8—C34—H34B109.5
C14—C13—C18122.5 (2)H34A—C34—H34B109.5
C15—C14—C13116.5 (2)O8—C34—H34C109.5
C15—C14—H14A121.7H34A—C34—H34C109.5
C13—C14—H14A121.7H34B—C34—H34C109.5
C14—C15—C16121.6 (2)O3—Cl—O4110.16 (19)
C14—C15—H15A119.2O3—Cl—O6109.73 (16)
C16—C15—H15A119.2O4—Cl—O6111.24 (17)
C17—C16—C15121.3 (2)O3—Cl—O5108.9 (2)
C17—C16—H16A119.3O4—Cl—O5108.55 (16)
C15—C16—H16A119.3O6—Cl—O5108.25 (14)
C16—C17—C18117.6 (2)

Symmetry codes: (i) −x−1, −y−1, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O8—H8O···O7ii0.841.932.768 (3)180

Symmetry codes: (ii) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2580).

References

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  • Bruker (1997). SHELXTL Bruker AXS Inc., Madison, Wisconsin, USA.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2004). RAPID-AUTO Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Youngme, S., Phatchimkun, J., Sukangpanya, U., Pakawatchai, C., Chaichit, N., Kongsaeree, P., Krzystek, J. & Murphy, B. (2007). Polyhedron, 26, 871–882.

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