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Acta Cryst. (2007). E63, m2582    [ doi:10.1107/S1600536807045953 ]

[5,10,15,20-Tetrakis(4-tert-butylphenyl)porphyrinato-[kappa]4N]zinc(II) toluene solvate

R. Slota, G. Mele, K. Ejsmont, A. A. Domanski and R. del Sole

Abstract top

The structure of the title compound, [Zn(C60H60N4)]·C7H8, represents a typical clathrate containing a host molecule of [5,10,15,20-tetrakis(4-tert-butylphenyl)porphyrinato]zinc(II) and a toluene guest molecule. The Zn atom occupies an inversion center and exhibits ideal square-planar coordination, while the porphyrin group remains perfectly flat. The toluene molecule lies on an inversion center and is disordered.

Comment top

Physicochemical properties of metallo-porphyrins depend on the complexed metal and the kind of peripherally and/or axially fixed substituents. These factors influence the electronic density distribution within the core of the macrocycle, thus determining both its stability and reactivity (Berezin, 1981). Therefore, structural details are essential in learning the basic chemistry of such compounds featuring unique properties, e.g. photocatalytic activity (Mele et al., 2007). 5,10,15,20-Tetrakis(4-tert-butylphenyl)porphyrinato zinc(II) (ZnPp), when crystallized from a toluene solution yielded a typical lattice clathrate with ZnPp (host) to toluene (guest) 1:1 stoichiometry. The structure of the title tert-butylphenyl meso-substituted ZnPp derivative has been solved and reported for the first time in this work.

The crystal lattice consists of discrete centrosymmetrical molecules of ZnPp (Fig. 1) and disordered molecules of toluene, located at the inversion centre. This is a typical case of toluene disorder exhibiting two discrete positions; one molecule is staggered 180° with respect to the other one. The zinc atom is found in a plane defined by the four pyrrole-nitrogen atoms and the N—Zn—N bond angles are ca 90°, showing ideal square-planar coordination. The macrocycle itself shows no apparent distortion and one may consider it as "perfectly flat". The meso substituted benzene rings are not perpendicular to the plane of the macrocycle, yielding dihedral angles of 78.44 (7)° and 79.17 (7)°. The geometry of the porphyrin core proved typical as for the family of similar zinc porphyrins substituted in their meso position by four identical phenyl derivatives (Allen, 2002). The unit cell packing of the title compound is shown in Fig. 2.

Related literature top

For related literature, see: Berezin (1981); Mele et al. (2003, 2007); Allen (2002).

Experimental top

5,10,15,20-tetrakis(4-tert-butylphenyl)porphyrinato zinc(II) was synthesized according to a typical procedure (Mele et al., 2003), applying ZnCl2 as the metal source. Pure monocrystals for X-ray diffraction measurements were obtained by multiple re-crystallization from toluene (reagent grade) at room temperature, yielding the final product in the form of a toluene solvate.

Refinement top

The hydrogen atoms were included in the refinement at geometrically idealized positions with C—H distances 0.96 Å for methyl and toluene solvate and 0.93 Å for the rest of the hydrogen atoms and Ueq = 1.5 and 1.2 times Ueq of the parent atoms, respectively. The toluene solvate was lying about inversion centers and was disordered.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% displacement ellipsoids and arbitrary spheres for the H atoms. Symmetry code: (i) −x + 1, −y + 1, −z + 1.
[Figure 2] Fig. 2. The packing diagram of the title compound.
[5,10,15,20-Tetrakis(4-tert-butylphenyl)porphyrinato-κ4N]zinc(II) toluene solvate top
Crystal data top
[Zn(C60H60N4)]·C7H8F000 = 1056
Mr = 994.64Dx = 1.277 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4533 reflections
a = 16.0277 (16) Åθ = 3.2–25.0º
b = 9.5884 (14) ŵ = 0.52 mm−1
c = 16.8714 (16) ÅT = 85.0 (1) K
β = 93.892 (8)ºPlate, colourless
V = 2586.8 (5) Å30.25 × 0.20 × 0.10 mm
Z = 2
Data collection top
Oxford Diffraction Xcalibur
diffractometer		4533 independent reflections
Radiation source: Enhanced (Mo) X-ray Source3375 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.060
Detector resolution: 1024x1024 with blocks 2x2 pixels mm-1θmax = 25.0º
T = 85.0(1) Kθmin = 3.2º
ω scansh = −18→19
Absorption correction: nonek = −7→11
14020 measured reflectionsl = −20→19
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 not refined
wR(F2) = 0.122  w = 1/[σ2(Fo2) + (0.0778P)2 + 0.1154P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
4533 reflectionsΔρmax = 0.42 e Å−3
341 parametersΔρmin = −0.37 e Å−3
93 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Zn(C60H60N4)]·C7H8V = 2586.8 (5) Å3
Mr = 994.64Z = 2
Monoclinic, P21/nMo Kα
a = 16.0277 (16) ŵ = 0.52 mm−1
b = 9.5884 (14) ÅT = 85.0 (1) K
c = 16.8714 (16) Å0.25 × 0.20 × 0.10 mm
β = 93.892 (8)º
Data collection top
Oxford Diffraction Xcalibur
diffractometer		4533 independent reflections
Absorption correction: none3375 reflections with I > 2σ(I)
14020 measured reflectionsRint = 0.060
Refinement top
R[F2 > 2σ(F2)] = 0.04693 restraints
wR(F2) = 0.122H-atom parameters not refined
S = 1.05Δρmax = 0.42 e Å−3
4533 reflectionsΔρmin = −0.37 e Å−3
341 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 > 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)
Zn10.50000.50000.50000.01341 (15)
N10.62401 (12)0.5020 (2)0.47623 (12)0.0138 (4)
N20.46708 (13)0.5079 (2)0.38213 (12)0.0140 (5)
C10.69152 (15)0.5006 (3)0.53100 (15)0.0132 (5)
C20.76805 (15)0.5049 (3)0.49013 (15)0.0141 (5)
H2A0.82220.50450.51360.017*
C30.74594 (15)0.5094 (3)0.41128 (16)0.0155 (5)
H3A0.78210.51310.37040.019*
C40.65585 (15)0.5073 (3)0.40256 (15)0.0132 (5)
C50.60800 (15)0.5118 (2)0.32961 (15)0.0134 (5)
C60.52031 (15)0.5115 (2)0.32132 (15)0.0134 (5)
C70.47170 (16)0.5157 (3)0.24613 (15)0.0150 (5)
H7A0.49240.51880.19600.018*
C80.39000 (16)0.5143 (3)0.26257 (15)0.0158 (6)
H8A0.34420.51670.22570.019*
C90.38730 (15)0.5085 (2)0.34701 (15)0.0126 (5)
C100.31249 (15)0.5036 (3)0.38640 (15)0.0132 (5)
C110.65151 (15)0.5163 (3)0.25357 (15)0.0144 (5)
C120.68218 (15)0.3966 (3)0.21983 (16)0.0185 (6)
H12A0.68490.31430.24900.022*
C130.70888 (16)0.3972 (3)0.14360 (16)0.0179 (6)
H13A0.72900.31500.12260.021*
C140.70640 (15)0.5172 (3)0.09771 (15)0.0161 (6)
C150.68138 (16)0.6404 (3)0.13437 (15)0.0187 (6)
H15A0.68320.72440.10700.022*
C160.65410 (16)0.6393 (3)0.21022 (16)0.0199 (6)
H16A0.63720.72230.23270.024*
C170.23273 (15)0.5053 (3)0.33498 (14)0.0136 (5)
C180.20367 (16)0.3871 (3)0.29459 (16)0.0194 (6)
H18A0.23180.30300.30310.023*
C190.13317 (16)0.3916 (3)0.24153 (16)0.0200 (6)
H19A0.11560.31080.21490.024*
C200.08848 (15)0.5146 (3)0.22766 (15)0.0152 (5)
C210.11813 (16)0.6330 (3)0.26884 (16)0.0202 (6)
H21A0.09000.71720.26070.024*
C220.18838 (16)0.6282 (3)0.32149 (16)0.0202 (6)
H22A0.20610.70890.34820.024*
C230.72525 (16)0.5201 (3)0.00997 (15)0.0169 (6)
C240.74775 (18)0.3764 (3)−0.02088 (17)0.0249 (7)
H24A0.79670.34230.00890.037*
H24B0.75870.3831−0.07600.037*
H24C0.70200.3134−0.01490.037*
C250.79766 (17)0.6211 (3)−0.00308 (16)0.0224 (6)
H25A0.84720.58980.02680.034*
H25B0.78330.71280.01430.034*
H25C0.80770.6238−0.05850.034*
C260.64640 (17)0.5725 (3)−0.03894 (16)0.0245 (7)
H26A0.60060.5103−0.03160.037*
H26B0.65720.5755−0.09420.037*
H26C0.63240.6643−0.02140.037*
C270.01147 (16)0.5261 (3)0.16840 (16)0.0183 (6)
C28−0.01266 (18)0.3852 (3)0.13143 (17)0.0258 (7)
H28A−0.02570.32110.17250.039*
H28B0.03320.34940.10380.039*
H28C−0.06070.39640.09480.039*
C290.03216 (18)0.6284 (3)0.10215 (17)0.0253 (7)
H29A−0.01530.63680.06460.038*
H29B0.07920.59390.07570.038*
H29C0.04550.71800.12490.038*
C30−0.06321 (17)0.5829 (4)0.21073 (18)0.0303 (7)
H30A−0.07650.51970.25220.045*
H30B−0.11070.59210.17320.045*
H30C−0.04920.67250.23330.045*
C310.9921 (2)0.5396 (5)0.4346 (2)0.0522 (10)
H310.99350.52120.37880.063*
C320.9924 (4)0.5772 (9)0.5186 (4)0.0404 (15)0.50
C330.9924 (4)0.5879 (8)0.5862 (4)0.0391 (16)0.50
H330.99300.60220.64260.047*0.50
C340.9744 (2)0.7095 (5)0.5393 (3)0.0689 (12)
H34A0.97730.71630.59620.103*0.50
H34B1.01410.77240.51860.103*0.50
H34C0.91910.73340.51840.103*0.50
H340.96320.80160.55820.083*0.50
C350.9769 (4)0.6616 (10)0.4494 (5)0.0597 (19)0.50
H350.96670.72770.40720.072*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0123 (2)0.0152 (2)0.0127 (2)0.00000 (17)0.00079 (15)0.00060 (18)
N10.0152 (11)0.0134 (11)0.0128 (11)0.0002 (9)−0.0001 (8)0.0003 (9)
N20.0113 (10)0.0149 (11)0.0159 (11)0.0009 (9)0.0011 (8)0.0009 (9)
C10.0151 (12)0.0092 (12)0.0153 (13)−0.0010 (10)0.0014 (10)0.0022 (11)
C20.0100 (12)0.0140 (13)0.0181 (13)−0.0007 (10)−0.0005 (10)0.0005 (11)
C30.0141 (12)0.0137 (13)0.0190 (14)0.0005 (11)0.0046 (10)0.0003 (11)
C40.0133 (12)0.0111 (12)0.0154 (13)0.0003 (10)0.0022 (10)0.0001 (11)
C50.0163 (13)0.0078 (12)0.0162 (13)0.0002 (10)0.0002 (10)−0.0003 (11)
C60.0173 (13)0.0092 (12)0.0136 (13)−0.0015 (10)0.0010 (10)−0.0011 (11)
C70.0177 (13)0.0161 (13)0.0113 (13)−0.0021 (11)0.0020 (10)0.0008 (11)
C80.0156 (13)0.0174 (14)0.0137 (13)0.0019 (11)−0.0037 (10)−0.0011 (11)
C90.0158 (13)0.0070 (12)0.0146 (13)0.0000 (10)−0.0019 (10)−0.0015 (11)
C100.0149 (12)0.0089 (12)0.0156 (13)−0.0005 (10)−0.0007 (10)−0.0013 (11)
C110.0109 (12)0.0188 (14)0.0130 (13)−0.0024 (10)−0.0018 (9)−0.0014 (11)
C120.0156 (13)0.0185 (14)0.0214 (15)0.0052 (11)0.0018 (11)0.0049 (12)
C130.0185 (14)0.0154 (14)0.0202 (14)0.0033 (11)0.0046 (11)0.0001 (11)
C140.0106 (12)0.0207 (14)0.0167 (13)−0.0010 (11)−0.0019 (10)−0.0012 (12)
C150.0217 (14)0.0147 (14)0.0199 (15)−0.0017 (11)0.0032 (11)0.0016 (12)
C160.0210 (14)0.0164 (14)0.0226 (15)−0.0022 (11)0.0039 (11)−0.0037 (12)
C170.0130 (12)0.0160 (13)0.0120 (12)−0.0005 (11)0.0035 (10)0.0011 (11)
C180.0208 (14)0.0144 (14)0.0223 (15)0.0036 (11)−0.0041 (11)−0.0003 (12)
C190.0227 (15)0.0151 (14)0.0213 (15)−0.0020 (11)−0.0049 (11)−0.0040 (12)
C200.0125 (12)0.0185 (14)0.0146 (13)−0.0016 (11)0.0002 (10)0.0022 (11)
C210.0200 (14)0.0153 (14)0.0248 (15)0.0043 (11)−0.0033 (11)0.0039 (12)
C220.0169 (14)0.0165 (14)0.0266 (16)−0.0017 (11)−0.0037 (11)−0.0030 (12)
C230.0163 (13)0.0180 (14)0.0163 (14)0.0013 (11)0.0011 (10)0.0007 (11)
C240.0306 (16)0.0256 (16)0.0192 (15)0.0001 (13)0.0067 (12)−0.0024 (13)
C250.0220 (15)0.0262 (16)0.0196 (15)−0.0001 (12)0.0054 (11)0.0011 (13)
C260.0236 (15)0.0333 (17)0.0160 (15)0.0008 (13)−0.0016 (11)−0.0021 (13)
C270.0147 (13)0.0233 (15)0.0165 (14)0.0010 (11)−0.0023 (10)−0.0013 (11)
C280.0249 (15)0.0256 (16)0.0253 (16)−0.0056 (12)−0.0094 (12)0.0000 (13)
C290.0240 (15)0.0263 (16)0.0245 (16)−0.0014 (13)−0.0048 (12)0.0062 (13)
C300.0159 (15)0.048 (2)0.0259 (17)0.0046 (14)−0.0048 (12)−0.0033 (15)
C310.0228 (18)0.096 (3)0.038 (2)−0.014 (2)−0.0018 (15)0.016 (2)
C320.013 (3)0.072 (4)0.035 (3)−0.013 (3)0.002 (3)−0.001 (3)
C330.022 (3)0.062 (4)0.033 (3)−0.012 (3)0.001 (3)−0.001 (3)
C340.0255 (19)0.086 (3)0.095 (3)−0.011 (2)0.003 (2)0.004 (2)
C350.031 (4)0.071 (4)0.075 (4)−0.017 (4)−0.011 (3)0.044 (4)
Geometric parameters (Å, °) top
Zn1—N22.024 (2)C21—H21A0.9300
Zn1—N12.054 (2)C22—H22A0.9300
N1—C11.374 (3)C23—C241.525 (4)
N1—C41.376 (3)C23—C251.539 (4)
N1—N22.882 (3)C23—C261.546 (4)
N2—C91.372 (3)C24—H24A0.9600
N2—C61.379 (3)C24—H24B0.9600
C1—C10i1.400 (4)C24—H24C0.9600
C1—C21.448 (3)C25—H25A0.9600
C2—C31.354 (4)C25—H25B0.9600
C2—H2A0.9300C25—H25C0.9600
C3—C41.442 (3)C26—H26A0.9600
C3—H3A0.9300C26—H26B0.9600
C4—C51.406 (4)C26—H26C0.9600
C5—C61.403 (4)C27—C281.527 (4)
C5—C111.502 (3)C27—C301.535 (4)
C6—C71.444 (3)C27—C291.540 (4)
C7—C81.357 (4)C28—H28A0.9600
C7—H7A0.9300C28—H28B0.9600
C8—C91.429 (3)C28—H28C0.9600
C8—H8A0.9300C29—H29A0.9600
C9—C101.411 (3)C29—H29B0.9600
C10—C1i1.400 (4)C29—H29C0.9600
C10—C171.496 (3)C30—H30A0.9600
C11—C121.386 (4)C30—H30B0.9600
C11—C161.390 (4)C30—H30C0.9600
C12—C131.383 (4)C31—C351.224 (10)
C12—H12A0.9300C31—C33ii1.300 (9)
C13—C141.386 (4)C31—C32ii1.383 (9)
C13—H13A0.9300C31—C321.461 (8)
C14—C151.404 (4)C31—H310.9601
C14—C231.531 (4)C32—C331.146 (9)
C15—C161.380 (4)C32—C341.352 (9)
C15—H15A0.9300C32—C31ii1.383 (9)
C16—H16A0.9300C32—C351.427 (11)
C17—C181.386 (4)C33—C31ii1.300 (9)
C17—C221.387 (4)C33—C341.428 (9)
C18—C191.394 (4)C33—H330.9600
C18—H18A0.9300C34—C351.588 (11)
C19—C201.392 (4)C34—H34A0.9600
C19—H19A0.9300C34—H34B0.9600
C20—C211.397 (4)C34—H34C0.9600
C20—C271.539 (3)C34—H340.9600
C21—C221.387 (4)C35—H350.9599
N2—Zn1—N2i180C23—C25—H25A109.5
N2—Zn1—N1i90.06 (8)C23—C25—H25B109.5
N2i—Zn1—N1i89.94 (8)H25A—C25—H25B109.5
N2—Zn1—N189.94 (8)C23—C25—H25C109.5
N2i—Zn1—N190.06 (8)H25A—C25—H25C109.5
N1i—Zn1—N1180.000 (1)H25B—C25—H25C109.5
C1—N1—C4106.52 (19)C23—C26—H26A109.5
C1—N1—Zn1126.63 (16)C23—C26—H26B109.5
C4—N1—Zn1126.84 (16)H26A—C26—H26B109.5
C1—N1—N2171.20 (17)C23—C26—H26C109.5
C4—N1—N282.24 (14)H26A—C26—H26C109.5
C9—N2—C6106.5 (2)H26B—C26—H26C109.5
C9—N2—Zn1126.69 (17)C28—C27—C30108.7 (2)
C6—N2—Zn1126.79 (17)C28—C27—C29109.1 (2)
C9—N2—N1172.12 (17)C30—C27—C29109.0 (2)
C6—N2—N181.34 (14)C28—C27—C20111.8 (2)
Zn1—N2—N145.45 (6)C30—C27—C20109.9 (2)
C6—N2—N1iii134.36 (14)C29—C27—C20108.3 (2)
Zn1—N2—N1iii96.26 (6)C27—C28—H28A109.5
N1—N2—N1iii139.30 (6)C27—C28—H28B109.5
N1—C1—C10i125.6 (2)H28A—C28—H28B109.5
N1—C1—C2109.5 (2)C27—C28—H28C109.5
C10i—C1—C2124.9 (2)H28A—C28—H28C109.5
C3—C2—C1107.2 (2)H28B—C28—H28C109.5
C3—C2—H2A126.4C27—C29—H29A109.5
C1—C2—H2A126.4C27—C29—H29B109.5
C2—C3—C4107.1 (2)H29A—C29—H29B109.5
C2—C3—H3A126.5C27—C29—H29C109.5
C4—C3—H3A126.5H29A—C29—H29C109.5
N1—C4—C5125.3 (2)H29B—C29—H29C109.5
N1—C4—C3109.8 (2)C27—C30—H30A109.5
C5—C4—C3124.9 (2)C27—C30—H30B109.5
C6—C5—C4124.8 (2)H30A—C30—H30B109.5
C6—C5—C11115.8 (2)C27—C30—H30C109.5
C4—C5—C11119.4 (2)H30A—C30—H30C109.5
N2—C6—C5126.3 (2)H30B—C30—H30C109.5
N2—C6—C7109.3 (2)C35—C31—C33ii176.1 (6)
C5—C6—C7124.4 (2)C35—C31—C32ii133.5 (6)
C8—C7—C6106.9 (2)C33ii—C31—C32ii50.5 (4)
C8—C7—H7A126.5C35—C31—C3263.5 (6)
C6—C7—H7A126.5C33ii—C31—C32120.4 (6)
C7—C8—C9107.4 (2)C32ii—C31—C3270.0 (6)
C7—C8—H8A126.3C35—C31—H31113.2
C9—C8—H8A126.3C33ii—C31—H3162.9
N2—C9—C10126.4 (2)C32ii—C31—H31113.3
N2—C9—C8109.9 (2)C32—C31—H31175.9
C10—C9—C8123.7 (2)C33—C32—C3469.1 (6)
C1i—C10—C9124.6 (2)C33—C32—C31ii61.0 (6)
C1i—C10—C17118.8 (2)C34—C32—C31ii130.2 (6)
C9—C10—C17116.5 (2)C33—C32—C35138.8 (9)
C12—C11—C16117.6 (2)C34—C32—C3569.6 (6)
C12—C11—C5121.7 (2)C31ii—C32—C35160.0 (8)
C16—C11—C5120.4 (2)C33—C32—C31170.8 (9)
C11—C12—C13121.3 (2)C34—C32—C31119.7 (6)
C11—C12—H12A119.4C31ii—C32—C31110.0 (6)
C13—C12—H12A119.4C35—C32—C3150.1 (5)
C12—C13—C14121.6 (2)C33—C32—C32ii118.2 (9)
C12—C13—H13A119.2C34—C32—C32ii172.0 (8)
C14—C13—H13A119.2C31ii—C32—C32ii57.2 (5)
C13—C14—C15116.8 (2)C35—C32—C32ii102.9 (8)
C13—C14—C23123.7 (2)C31—C32—C32ii52.7 (4)
C15—C14—C23119.4 (2)C32—C33—C31ii68.5 (6)
C16—C15—C14121.3 (2)C32—C33—C3462.2 (6)
C16—C15—H15A119.3C31ii—C33—C34130.7 (6)
C14—C15—H15A119.3C32—C33—H33176.9
C15—C16—C11121.1 (2)C31ii—C33—H33114.4
C15—C16—H16A119.4C34—C33—H33114.8
C11—C16—H16A119.4C32—C33—H34A103.4
C18—C17—C22117.5 (2)C31ii—C33—H34A171.9
C18—C17—C10121.4 (2)H33—C33—H34A73.7
C22—C17—C10120.9 (2)C32—C34—C3348.6 (4)
C17—C18—C19121.4 (2)C32—C34—C3557.4 (5)
C17—C18—H18A119.3C33—C34—C35106.0 (5)
C19—C18—H18A119.3C32—C34—H34A109.0
C20—C19—C18121.3 (2)C33—C34—H34A60.5
C20—C19—H19A119.3C35—C34—H34A166.4
C18—C19—H19A119.3C32—C34—H34B109.7
C19—C20—C21116.8 (2)C33—C34—H34B127.0
C19—C20—C27123.4 (2)C35—C34—H34B76.9
C21—C20—C27119.7 (2)H34A—C34—H34B109.5
C22—C21—C20121.7 (2)C32—C34—H34C109.7
C22—C21—H21A119.1C33—C34—H34C123.1
C20—C21—H21A119.1C35—C34—H34C78.4
C17—C22—C21121.2 (2)H34A—C34—H34C109.5
C17—C22—H22A119.4H34B—C34—H34C109.5
C21—C22—H22A119.4C32—C34—H34175.5
C24—C23—C14112.4 (2)C33—C34—H34127.0
C24—C23—C25108.8 (2)C35—C34—H34126.9
C14—C23—C25110.5 (2)H34A—C34—H3466.6
C24—C23—C26108.4 (2)H34B—C34—H3471.8
C14—C23—C26108.3 (2)H34C—C34—H3473.3
C25—C23—C26108.4 (2)C31—C35—C3266.4 (5)
C23—C24—H24A109.5C31—C35—C34119.3 (6)
C23—C24—H24B109.5C32—C35—C3452.9 (5)
H24A—C24—H24B109.5C31—C35—H35120.4
C23—C24—H24C109.5C32—C35—H35173.1
H24A—C24—H24C109.5C34—C35—H35120.3
H24B—C24—H24C109.5
N2—Zn1—N1—C1178.9 (2)C12—C13—C14—C23−172.5 (2)
N2i—Zn1—N1—C1−1.1 (2)C13—C14—C15—C16−5.1 (4)
N2—Zn1—N1—C40.1 (2)C23—C14—C15—C16172.1 (2)
N2i—Zn1—N1—C4−179.9 (2)C14—C15—C16—C110.9 (4)
N2i—Zn1—N1—N2180.0C12—C11—C16—C153.9 (4)
N1i—Zn1—N2—C9−0.8 (2)C5—C11—C16—C15−169.3 (2)
N1—Zn1—N2—C9179.2 (2)C1i—C10—C17—C18−103.8 (3)
N1i—Zn1—N2—C6−179.6 (2)C9—C10—C17—C1877.2 (3)
N1—Zn1—N2—C60.4 (2)C1i—C10—C17—C2281.0 (3)
N1i—Zn1—N2—N1180.0C9—C10—C17—C22−98.0 (3)
N1i—Zn1—N2—N1iii−15.84 (6)C22—C17—C18—C190.8 (4)
N1—Zn1—N2—N1iii164.16 (6)C10—C17—C18—C19−174.5 (2)
C4—N1—N2—C60.37 (18)C17—C18—C19—C20−0.8 (4)
Zn1—N1—N2—C6−179.72 (16)C18—C19—C20—C210.5 (4)
C4—N1—N2—Zn1−179.92 (16)C18—C19—C20—C27178.6 (2)
C4—N1—N2—N1iii155.51 (13)C19—C20—C21—C22−0.4 (4)
Zn1—N1—N2—N1iii−24.58 (8)C27—C20—C21—C22−178.6 (2)
C4—N1—C1—C10i179.6 (2)C18—C17—C22—C21−0.7 (4)
Zn1—N1—C1—C10i0.6 (4)C10—C17—C22—C21174.7 (2)
C4—N1—C1—C2−0.2 (3)C20—C21—C22—C170.5 (4)
Zn1—N1—C1—C2−179.16 (16)C13—C14—C23—C24−0.5 (3)
N1—C1—C2—C30.3 (3)C15—C14—C23—C24−177.5 (2)
C10i—C1—C2—C3−179.5 (2)C13—C14—C23—C25−122.2 (3)
C1—C2—C3—C4−0.3 (3)C15—C14—C23—C2560.8 (3)
C1—N1—C4—C5−179.3 (2)C13—C14—C23—C26119.2 (3)
Zn1—N1—C4—C5−0.3 (4)C15—C14—C23—C26−57.8 (3)
N2—N1—C4—C5−0.2 (2)C19—C20—C27—C283.7 (4)
C1—N1—C4—C30.0 (3)C21—C20—C27—C28−178.3 (2)
Zn1—N1—C4—C3178.98 (15)C19—C20—C27—C30124.5 (3)
N2—N1—C4—C3179.06 (19)C21—C20—C27—C30−57.5 (3)
C2—C3—C4—N10.2 (3)C19—C20—C27—C29−116.6 (3)
C2—C3—C4—C5179.4 (2)C21—C20—C27—C2961.4 (3)
N1—C4—C5—C60.0 (4)C35—C31—C32—C341.4 (6)
C3—C4—C5—C6−179.2 (2)C33ii—C31—C32—C34−178.6 (5)
N1—C4—C5—C11−179.5 (2)C32ii—C31—C32—C34−176.6 (8)
C3—C4—C5—C111.3 (4)C35—C31—C32—C31ii178.1 (6)
C9—N2—C6—C5−179.8 (2)C33ii—C31—C32—C31ii−2.0 (6)
Zn1—N2—C6—C5−0.7 (4)C32ii—C31—C32—C31ii0.0
N1—N2—C6—C5−0.5 (2)C33ii—C31—C32—C35180.0 (6)
N1iii—N2—C6—C5−157.91 (17)C32ii—C31—C32—C35−178.1 (6)
C9—N2—C6—C70.5 (3)C35—C31—C32—C32ii178.1 (6)
Zn1—N2—C6—C7179.57 (16)C33ii—C31—C32—C32ii−2.0 (6)
N1—N2—C6—C7179.82 (19)C34—C32—C33—C31ii178.7 (4)
N1iii—N2—C6—C722.4 (3)C35—C32—C33—C31ii176.6 (9)
C4—C5—C6—N20.6 (4)C32ii—C32—C33—C31ii2.1 (6)
C11—C5—C6—N2−179.9 (2)C31ii—C32—C33—C34−178.7 (4)
C4—C5—C6—C7−179.8 (2)C35—C32—C33—C34−2.0 (8)
C11—C5—C6—C7−0.3 (4)C32ii—C32—C33—C34−176.6 (8)
N2—C6—C7—C8−0.1 (3)C31ii—C32—C34—C331.5 (5)
C5—C6—C7—C8−179.8 (2)C35—C32—C34—C33178.6 (6)
C6—C7—C8—C9−0.3 (3)C31—C32—C34—C33177.4 (7)
C6—N2—C9—C10179.0 (2)C33—C32—C34—C35−178.6 (6)
Zn1—N2—C9—C100.0 (3)C31ii—C32—C34—C35−177.0 (8)
N1iii—N2—C9—C1027.91 (17)C31—C32—C34—C35−1.2 (5)
C6—N2—C9—C8−0.7 (3)C31ii—C33—C34—C32−1.6 (6)
Zn1—N2—C9—C8−179.78 (16)C32—C33—C34—C351.3 (5)
N1iii—N2—C9—C8−151.8 (3)C31ii—C33—C34—C35−0.4 (8)
C7—C8—C9—N20.7 (3)C32ii—C31—C35—C322.5 (8)
C7—C8—C9—C10−179.1 (2)C32ii—C31—C35—C341.3 (10)
N2—C9—C10—C1i1.0 (4)C32—C31—C35—C34−1.2 (5)
C8—C9—C10—C1i−179.3 (2)C33—C32—C35—C31−176.6 (9)
N2—C9—C10—C17−180.0 (2)C34—C32—C35—C31−178.7 (5)
C8—C9—C10—C17−0.3 (4)C31ii—C32—C35—C31−5.3 (17)
C6—C5—C11—C12−98.2 (3)C32ii—C32—C35—C31−1.6 (5)
C4—C5—C11—C1281.3 (3)C33—C32—C35—C342.0 (8)
C6—C5—C11—C1674.7 (3)C31ii—C32—C35—C34173.3 (17)
C4—C5—C11—C16−105.8 (3)C31—C32—C35—C34178.7 (5)
C16—C11—C12—C13−4.5 (4)C32ii—C32—C35—C34177.1 (7)
C5—C11—C12—C13168.6 (2)C32—C34—C35—C311.4 (5)
C11—C12—C13—C140.2 (4)C33—C34—C35—C310.3 (7)
C12—C13—C14—C154.6 (4)C33—C34—C35—C32−1.1 (5)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1; (iii) −x−1, −y, −z+1.
Table 1
Selected geometric parameters (Å, °) top
Zn1—N22.024 (2)Zn1—N12.054 (2)
N2—Zn1—N2i180N2—Zn1—N189.94 (8)
N2—Zn1—N1i90.06 (8)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Acknowledgements top

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references
References top

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Berezin, B. D. (1981). Coordination Compounds of Porphyrins and Phthalocyanines, pp. 5–42. New York: Willey and Sons.

Mele, G., Del Sole, R., Vasapollo, G., Garcia-López, E., Palmisano, L., Li, J., Słota, R. & Dyrda, G. (2007). Res. Chem. Intermed. pp. 433–438.

Mele, G., Del Sole, R., Vasapollo, G., Garcia-López, E., Palmisano, L. & Schiavello, M. (2003). J. Catal. 217, 334–342.

Oxford Diffraction (2002). CrysAlis CCD. Version 1.171. Oxford Diffraction, Wrocław, Poland.

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Sheldrick, G. M. (1990). SHELXTL. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.