[5,10,15,20-Tetra­kis(4-tert-butyl­phen­yl)­porphyrinato-κ4N]zinc(II) toluene solvate

Słota, R.; Mele, G.; Ejsmont, K.; Domański, A.A.; Sole, R. del

doi:10.1107/S1600536807045953

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[5,10,15,20-Tetrakis(4-tert-butylphenyl)porphyrinato-κ⁴N]zinc(II) toluene solvate

R. Słota, G. Mele, K. Ejsmont, A. A. Domański and R. del Sole

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045953/pv2028sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045953/pv2028Isup2.hkl Contains datablock I

CCDC reference: 299597

checkCIF report

Key indicators

Single-crystal X-ray study
T = 85 K
Mean (C-C) = 0.004 Å
Disorder in solvent or counterion
R factor = 0.046
wR factor = 0.122
Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT413_ALERT_2_B Short Inter XH3 .. XHn     H24C   ..  H34C    ..       2.08 Ang.

Alert level C
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C34
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      30.00 Perc.
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H26C   ..  H34B    ..       2.14 Ang.

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         93

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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.

Structure description top

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

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

	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.
	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)]·C₇H₈	F(000) = 1056
M_r = 994.64	D_x = 1.277 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4533 reflections
a = 16.0277 (16) Å	θ = 3.2–25.0°
b = 9.5884 (14) Å	µ = 0.52 mm⁻¹
c = 16.8714 (16) Å	T = 85 K
β = 93.892 (8)°	Plate, colourless
V = 2586.8 (5) Å³	0.25 × 0.20 × 0.10 mm
Z = 2

Data collection top

Oxford Diffraction Xcalibur diffractometer	3375 reflections with I > 2σ(I)
Radiation source: Enhanced (Mo) X-ray Source	R_int = 0.060
Graphite monochromator	θ_max = 25.0°, θ_min = 3.2°
Detector resolution: 1024x1024 with blocks 2x2 pixels mm^-1	h = −18→19
ω scans	k = −7→11
14020 measured reflections	l = −20→19
4533 independent reflections

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters not refined
S = 1.05	w = 1/[σ²(F_o²) + (0.0778P)² + 0.1154P] where P = (F_o² + 2F_c²)/3
4533 reflections	(Δ/σ)_max < 0.001
341 parameters	Δρ_max = 0.42 e Å⁻³
93 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Zn(C₆₀H₆₀N₄)]·C₇H₈	V = 2586.8 (5) Å³
M_r = 994.64	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 16.0277 (16) Å	µ = 0.52 mm⁻¹
b = 9.5884 (14) Å	T = 85 K
c = 16.8714 (16) Å	0.25 × 0.20 × 0.10 mm
β = 93.892 (8)°

Data collection top

Oxford Diffraction Xcalibur diffractometer	3375 reflections with I > 2σ(I)
14020 measured reflections	R_int = 0.060
4533 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	93 restraints
wR(F²) = 0.122	H-atom parameters not refined
S = 1.05	Δρ_max = 0.42 e Å⁻³
4533 reflections	Δρ_min = −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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Zn1	0.5000	0.5000	0.5000	0.01341 (15)
N1	0.62401 (12)	0.5020 (2)	0.47623 (12)	0.0138 (4)
N2	0.46708 (13)	0.5079 (2)	0.38213 (12)	0.0140 (5)
C1	0.69152 (15)	0.5006 (3)	0.53100 (15)	0.0132 (5)
C2	0.76805 (15)	0.5049 (3)	0.49013 (15)	0.0141 (5)
H2A	0.8222	0.5045	0.5136	0.017*
C3	0.74594 (15)	0.5094 (3)	0.41128 (16)	0.0155 (5)
H3A	0.7821	0.5131	0.3704	0.019*
C4	0.65585 (15)	0.5073 (3)	0.40256 (15)	0.0132 (5)
C5	0.60800 (15)	0.5118 (2)	0.32961 (15)	0.0134 (5)
C6	0.52031 (15)	0.5115 (2)	0.32132 (15)	0.0134 (5)
C7	0.47170 (16)	0.5157 (3)	0.24613 (15)	0.0150 (5)
H7A	0.4924	0.5188	0.1960	0.018*
C8	0.39000 (16)	0.5143 (3)	0.26257 (15)	0.0158 (6)
H8A	0.3442	0.5167	0.2257	0.019*
C9	0.38730 (15)	0.5085 (2)	0.34701 (15)	0.0126 (5)
C10	0.31249 (15)	0.5036 (3)	0.38640 (15)	0.0132 (5)
C11	0.65151 (15)	0.5163 (3)	0.25357 (15)	0.0144 (5)
C12	0.68218 (15)	0.3966 (3)	0.21983 (16)	0.0185 (6)
H12A	0.6849	0.3143	0.2490	0.022*
C13	0.70888 (16)	0.3972 (3)	0.14360 (16)	0.0179 (6)
H13A	0.7290	0.3150	0.1226	0.021*
C14	0.70640 (15)	0.5172 (3)	0.09771 (15)	0.0161 (6)
C15	0.68138 (16)	0.6404 (3)	0.13437 (15)	0.0187 (6)
H15A	0.6832	0.7244	0.1070	0.022*
C16	0.65410 (16)	0.6393 (3)	0.21022 (16)	0.0199 (6)
H16A	0.6372	0.7223	0.2327	0.024*
C17	0.23273 (15)	0.5053 (3)	0.33498 (14)	0.0136 (5)
C18	0.20367 (16)	0.3871 (3)	0.29459 (16)	0.0194 (6)
H18A	0.2318	0.3030	0.3031	0.023*
C19	0.13317 (16)	0.3916 (3)	0.24153 (16)	0.0200 (6)
H19A	0.1156	0.3108	0.2149	0.024*
C20	0.08848 (15)	0.5146 (3)	0.22766 (15)	0.0152 (5)
C21	0.11813 (16)	0.6330 (3)	0.26884 (16)	0.0202 (6)
H21A	0.0900	0.7172	0.2607	0.024*
C22	0.18838 (16)	0.6282 (3)	0.32149 (16)	0.0202 (6)
H22A	0.2061	0.7089	0.3482	0.024*
C23	0.72525 (16)	0.5201 (3)	0.00997 (15)	0.0169 (6)
C24	0.74775 (18)	0.3764 (3)	−0.02088 (17)	0.0249 (7)
H24A	0.7967	0.3423	0.0089	0.037*
H24B	0.7587	0.3831	−0.0760	0.037*
H24C	0.7020	0.3134	−0.0149	0.037*
C25	0.79766 (17)	0.6211 (3)	−0.00308 (16)	0.0224 (6)
H25A	0.8472	0.5898	0.0268	0.034*
H25B	0.7833	0.7128	0.0143	0.034*
H25C	0.8077	0.6238	−0.0585	0.034*
C26	0.64640 (17)	0.5725 (3)	−0.03894 (16)	0.0245 (7)
H26A	0.6006	0.5103	−0.0316	0.037*
H26B	0.6572	0.5755	−0.0942	0.037*
H26C	0.6324	0.6643	−0.0214	0.037*
C27	0.01147 (16)	0.5261 (3)	0.16840 (16)	0.0183 (6)
C28	−0.01266 (18)	0.3852 (3)	0.13143 (17)	0.0258 (7)
H28A	−0.0257	0.3211	0.1725	0.039*
H28B	0.0332	0.3494	0.1038	0.039*
H28C	−0.0607	0.3964	0.0948	0.039*
C29	0.03216 (18)	0.6284 (3)	0.10215 (17)	0.0253 (7)
H29A	−0.0153	0.6368	0.0646	0.038*
H29B	0.0792	0.5939	0.0757	0.038*
H29C	0.0455	0.7180	0.1249	0.038*
C30	−0.06321 (17)	0.5829 (4)	0.21073 (18)	0.0303 (7)
H30A	−0.0765	0.5197	0.2522	0.045*
H30B	−0.1107	0.5921	0.1732	0.045*
H30C	−0.0492	0.6725	0.2333	0.045*
C31	0.9921 (2)	0.5396 (5)	0.4346 (2)	0.0522 (10)
H31	0.9935	0.5212	0.3788	0.063*
C32	0.9924 (4)	0.5772 (9)	0.5186 (4)	0.0404 (15)	0.50
C33	0.9924 (4)	0.5879 (8)	0.5862 (4)	0.0391 (16)	0.50
H33	0.9930	0.6022	0.6426	0.047*	0.50
C34	0.9744 (2)	0.7095 (5)	0.5393 (3)	0.0689 (12)
H34A	0.9773	0.7163	0.5962	0.103*	0.50
H34B	1.0141	0.7724	0.5186	0.103*	0.50
H34C	0.9191	0.7334	0.5184	0.103*	0.50
H34	0.9632	0.8016	0.5582	0.083*	0.50
C35	0.9769 (4)	0.6616 (10)	0.4494 (5)	0.0597 (19)	0.50
H35	0.9667	0.7277	0.4072	0.072*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0123 (2)	0.0152 (2)	0.0127 (2)	0.00000 (17)	0.00079 (15)	0.00060 (18)
N1	0.0152 (11)	0.0134 (11)	0.0128 (11)	0.0002 (9)	−0.0001 (8)	0.0003 (9)
N2	0.0113 (10)	0.0149 (11)	0.0159 (11)	0.0009 (9)	0.0011 (8)	0.0009 (9)
C1	0.0151 (12)	0.0092 (12)	0.0153 (13)	−0.0010 (10)	0.0014 (10)	0.0022 (11)
C2	0.0100 (12)	0.0140 (13)	0.0181 (13)	−0.0007 (10)	−0.0005 (10)	0.0005 (11)
C3	0.0141 (12)	0.0137 (13)	0.0190 (14)	0.0005 (11)	0.0046 (10)	0.0003 (11)
C4	0.0133 (12)	0.0111 (12)	0.0154 (13)	0.0003 (10)	0.0022 (10)	0.0001 (11)
C5	0.0163 (13)	0.0078 (12)	0.0162 (13)	0.0002 (10)	0.0002 (10)	−0.0003 (11)
C6	0.0173 (13)	0.0092 (12)	0.0136 (13)	−0.0015 (10)	0.0010 (10)	−0.0011 (11)
C7	0.0177 (13)	0.0161 (13)	0.0113 (13)	−0.0021 (11)	0.0020 (10)	0.0008 (11)
C8	0.0156 (13)	0.0174 (14)	0.0137 (13)	0.0019 (11)	−0.0037 (10)	−0.0011 (11)
C9	0.0158 (13)	0.0070 (12)	0.0146 (13)	0.0000 (10)	−0.0019 (10)	−0.0015 (11)
C10	0.0149 (12)	0.0089 (12)	0.0156 (13)	−0.0005 (10)	−0.0007 (10)	−0.0013 (11)
C11	0.0109 (12)	0.0188 (14)	0.0130 (13)	−0.0024 (10)	−0.0018 (9)	−0.0014 (11)
C12	0.0156 (13)	0.0185 (14)	0.0214 (15)	0.0052 (11)	0.0018 (11)	0.0049 (12)
C13	0.0185 (14)	0.0154 (14)	0.0202 (14)	0.0033 (11)	0.0046 (11)	0.0001 (11)
C14	0.0106 (12)	0.0207 (14)	0.0167 (13)	−0.0010 (11)	−0.0019 (10)	−0.0012 (12)
C15	0.0217 (14)	0.0147 (14)	0.0199 (15)	−0.0017 (11)	0.0032 (11)	0.0016 (12)
C16	0.0210 (14)	0.0164 (14)	0.0226 (15)	−0.0022 (11)	0.0039 (11)	−0.0037 (12)
C17	0.0130 (12)	0.0160 (13)	0.0120 (12)	−0.0005 (11)	0.0035 (10)	0.0011 (11)
C18	0.0208 (14)	0.0144 (14)	0.0223 (15)	0.0036 (11)	−0.0041 (11)	−0.0003 (12)
C19	0.0227 (15)	0.0151 (14)	0.0213 (15)	−0.0020 (11)	−0.0049 (11)	−0.0040 (12)
C20	0.0125 (12)	0.0185 (14)	0.0146 (13)	−0.0016 (11)	0.0002 (10)	0.0022 (11)
C21	0.0200 (14)	0.0153 (14)	0.0248 (15)	0.0043 (11)	−0.0033 (11)	0.0039 (12)
C22	0.0169 (14)	0.0165 (14)	0.0266 (16)	−0.0017 (11)	−0.0037 (11)	−0.0030 (12)
C23	0.0163 (13)	0.0180 (14)	0.0163 (14)	0.0013 (11)	0.0011 (10)	0.0007 (11)
C24	0.0306 (16)	0.0256 (16)	0.0192 (15)	0.0001 (13)	0.0067 (12)	−0.0024 (13)
C25	0.0220 (15)	0.0262 (16)	0.0196 (15)	−0.0001 (12)	0.0054 (11)	0.0011 (13)
C26	0.0236 (15)	0.0333 (17)	0.0160 (15)	0.0008 (13)	−0.0016 (11)	−0.0021 (13)
C27	0.0147 (13)	0.0233 (15)	0.0165 (14)	0.0010 (11)	−0.0023 (10)	−0.0013 (11)
C28	0.0249 (15)	0.0256 (16)	0.0253 (16)	−0.0056 (12)	−0.0094 (12)	0.0000 (13)
C29	0.0240 (15)	0.0263 (16)	0.0245 (16)	−0.0014 (13)	−0.0048 (12)	0.0062 (13)
C30	0.0159 (15)	0.048 (2)	0.0259 (17)	0.0046 (14)	−0.0048 (12)	−0.0033 (15)
C31	0.0228 (18)	0.096 (3)	0.038 (2)	−0.014 (2)	−0.0018 (15)	0.016 (2)
C32	0.013 (3)	0.072 (4)	0.035 (3)	−0.013 (3)	0.002 (3)	−0.001 (3)
C33	0.022 (3)	0.062 (4)	0.033 (3)	−0.012 (3)	0.001 (3)	−0.001 (3)
C34	0.0255 (19)	0.086 (3)	0.095 (3)	−0.011 (2)	0.003 (2)	0.004 (2)
C35	0.031 (4)	0.071 (4)	0.075 (4)	−0.017 (4)	−0.011 (3)	0.044 (4)

Geometric parameters (Å, º) top

Zn1—N2	2.024 (2)	C21—H21A	0.9300
Zn1—N1	2.054 (2)	C22—H22A	0.9300
N1—C1	1.374 (3)	C23—C24	1.525 (4)
N1—C4	1.376 (3)	C23—C25	1.539 (4)
N1—N2	2.882 (3)	C23—C26	1.546 (4)
N2—C9	1.372 (3)	C24—H24A	0.9600
N2—C6	1.379 (3)	C24—H24B	0.9600
C1—C10ⁱ	1.400 (4)	C24—H24C	0.9600
C1—C2	1.448 (3)	C25—H25A	0.9600
C2—C3	1.354 (4)	C25—H25B	0.9600
C2—H2A	0.9300	C25—H25C	0.9600
C3—C4	1.442 (3)	C26—H26A	0.9600
C3—H3A	0.9300	C26—H26B	0.9600
C4—C5	1.406 (4)	C26—H26C	0.9600
C5—C6	1.403 (4)	C27—C28	1.527 (4)
C5—C11	1.502 (3)	C27—C30	1.535 (4)
C6—C7	1.444 (3)	C27—C29	1.540 (4)
C7—C8	1.357 (4)	C28—H28A	0.9600
C7—H7A	0.9300	C28—H28B	0.9600
C8—C9	1.429 (3)	C28—H28C	0.9600
C8—H8A	0.9300	C29—H29A	0.9600
C9—C10	1.411 (3)	C29—H29B	0.9600
C10—C1ⁱ	1.400 (4)	C29—H29C	0.9600
C10—C17	1.496 (3)	C30—H30A	0.9600
C11—C12	1.386 (4)	C30—H30B	0.9600
C11—C16	1.390 (4)	C30—H30C	0.9600
C12—C13	1.383 (4)	C31—C35	1.224 (10)
C12—H12A	0.9300	C31—C33ⁱⁱ	1.300 (9)
C13—C14	1.386 (4)	C31—C32ⁱⁱ	1.383 (9)
C13—H13A	0.9300	C31—C32	1.461 (8)
C14—C15	1.404 (4)	C31—H31	0.9601
C14—C23	1.531 (4)	C32—C33	1.146 (9)
C15—C16	1.380 (4)	C32—C34	1.352 (9)
C15—H15A	0.9300	C32—C31ⁱⁱ	1.383 (9)
C16—H16A	0.9300	C32—C35	1.427 (11)
C17—C18	1.386 (4)	C33—C31ⁱⁱ	1.300 (9)
C17—C22	1.387 (4)	C33—C34	1.428 (9)
C18—C19	1.394 (4)	C33—H33	0.9600
C18—H18A	0.9300	C34—C35	1.588 (11)
C19—C20	1.392 (4)	C34—H34A	0.9600
C19—H19A	0.9300	C34—H34B	0.9600
C20—C21	1.397 (4)	C34—H34C	0.9600
C20—C27	1.539 (3)	C34—H34	0.9600
C21—C22	1.387 (4)	C35—H35	0.9599

N2—Zn1—N2ⁱ	180	C23—C25—H25A	109.5
N2—Zn1—N1ⁱ	90.06 (8)	C23—C25—H25B	109.5
N2ⁱ—Zn1—N1ⁱ	89.94 (8)	H25A—C25—H25B	109.5
N2—Zn1—N1	89.94 (8)	C23—C25—H25C	109.5
N2ⁱ—Zn1—N1	90.06 (8)	H25A—C25—H25C	109.5
N1ⁱ—Zn1—N1	180.000 (1)	H25B—C25—H25C	109.5
C1—N1—C4	106.52 (19)	C23—C26—H26A	109.5
C1—N1—Zn1	126.63 (16)	C23—C26—H26B	109.5
C4—N1—Zn1	126.84 (16)	H26A—C26—H26B	109.5
C1—N1—N2	171.20 (17)	C23—C26—H26C	109.5
C4—N1—N2	82.24 (14)	H26A—C26—H26C	109.5
C9—N2—C6	106.5 (2)	H26B—C26—H26C	109.5
C9—N2—Zn1	126.69 (17)	C28—C27—C30	108.7 (2)
C6—N2—Zn1	126.79 (17)	C28—C27—C29	109.1 (2)
C9—N2—N1	172.12 (17)	C30—C27—C29	109.0 (2)
C6—N2—N1	81.34 (14)	C28—C27—C20	111.8 (2)
Zn1—N2—N1	45.45 (6)	C30—C27—C20	109.9 (2)
C6—N2—N1ⁱⁱⁱ	134.36 (14)	C29—C27—C20	108.3 (2)
Zn1—N2—N1ⁱⁱⁱ	96.26 (6)	C27—C28—H28A	109.5
N1—N2—N1ⁱⁱⁱ	139.30 (6)	C27—C28—H28B	109.5
N1—C1—C10ⁱ	125.6 (2)	H28A—C28—H28B	109.5
N1—C1—C2	109.5 (2)	C27—C28—H28C	109.5
C10ⁱ—C1—C2	124.9 (2)	H28A—C28—H28C	109.5
C3—C2—C1	107.2 (2)	H28B—C28—H28C	109.5
C3—C2—H2A	126.4	C27—C29—H29A	109.5
C1—C2—H2A	126.4	C27—C29—H29B	109.5
C2—C3—C4	107.1 (2)	H29A—C29—H29B	109.5
C2—C3—H3A	126.5	C27—C29—H29C	109.5
C4—C3—H3A	126.5	H29A—C29—H29C	109.5
N1—C4—C5	125.3 (2)	H29B—C29—H29C	109.5
N1—C4—C3	109.8 (2)	C27—C30—H30A	109.5
C5—C4—C3	124.9 (2)	C27—C30—H30B	109.5
C6—C5—C4	124.8 (2)	H30A—C30—H30B	109.5
C6—C5—C11	115.8 (2)	C27—C30—H30C	109.5
C4—C5—C11	119.4 (2)	H30A—C30—H30C	109.5
N2—C6—C5	126.3 (2)	H30B—C30—H30C	109.5
N2—C6—C7	109.3 (2)	C35—C31—C33ⁱⁱ	176.1 (6)
C5—C6—C7	124.4 (2)	C35—C31—C32ⁱⁱ	133.5 (6)
C8—C7—C6	106.9 (2)	C33ⁱⁱ—C31—C32ⁱⁱ	50.5 (4)
C8—C7—H7A	126.5	C35—C31—C32	63.5 (6)
C6—C7—H7A	126.5	C33ⁱⁱ—C31—C32	120.4 (6)
C7—C8—C9	107.4 (2)	C32ⁱⁱ—C31—C32	70.0 (6)
C7—C8—H8A	126.3	C35—C31—H31	113.2
C9—C8—H8A	126.3	C33ⁱⁱ—C31—H31	62.9
N2—C9—C10	126.4 (2)	C32ⁱⁱ—C31—H31	113.3
N2—C9—C8	109.9 (2)	C32—C31—H31	175.9
C10—C9—C8	123.7 (2)	C33—C32—C34	69.1 (6)
C1ⁱ—C10—C9	124.6 (2)	C33—C32—C31ⁱⁱ	61.0 (6)
C1ⁱ—C10—C17	118.8 (2)	C34—C32—C31ⁱⁱ	130.2 (6)
C9—C10—C17	116.5 (2)	C33—C32—C35	138.8 (9)
C12—C11—C16	117.6 (2)	C34—C32—C35	69.6 (6)
C12—C11—C5	121.7 (2)	C31ⁱⁱ—C32—C35	160.0 (8)
C16—C11—C5	120.4 (2)	C33—C32—C31	170.8 (9)
C11—C12—C13	121.3 (2)	C34—C32—C31	119.7 (6)
C11—C12—H12A	119.4	C31ⁱⁱ—C32—C31	110.0 (6)
C13—C12—H12A	119.4	C35—C32—C31	50.1 (5)
C12—C13—C14	121.6 (2)	C33—C32—C32ⁱⁱ	118.2 (9)
C12—C13—H13A	119.2	C34—C32—C32ⁱⁱ	172.0 (8)
C14—C13—H13A	119.2	C31ⁱⁱ—C32—C32ⁱⁱ	57.2 (5)
C13—C14—C15	116.8 (2)	C35—C32—C32ⁱⁱ	102.9 (8)
C13—C14—C23	123.7 (2)	C31—C32—C32ⁱⁱ	52.7 (4)
C15—C14—C23	119.4 (2)	C32—C33—C31ⁱⁱ	68.5 (6)
C16—C15—C14	121.3 (2)	C32—C33—C34	62.2 (6)
C16—C15—H15A	119.3	C31ⁱⁱ—C33—C34	130.7 (6)
C14—C15—H15A	119.3	C32—C33—H33	176.9
C15—C16—C11	121.1 (2)	C31ⁱⁱ—C33—H33	114.4
C15—C16—H16A	119.4	C34—C33—H33	114.8
C11—C16—H16A	119.4	C32—C33—H34A	103.4
C18—C17—C22	117.5 (2)	C31ⁱⁱ—C33—H34A	171.9
C18—C17—C10	121.4 (2)	H33—C33—H34A	73.7
C22—C17—C10	120.9 (2)	C32—C34—C33	48.6 (4)
C17—C18—C19	121.4 (2)	C32—C34—C35	57.4 (5)
C17—C18—H18A	119.3	C33—C34—C35	106.0 (5)
C19—C18—H18A	119.3	C32—C34—H34A	109.0
C20—C19—C18	121.3 (2)	C33—C34—H34A	60.5
C20—C19—H19A	119.3	C35—C34—H34A	166.4
C18—C19—H19A	119.3	C32—C34—H34B	109.7
C19—C20—C21	116.8 (2)	C33—C34—H34B	127.0
C19—C20—C27	123.4 (2)	C35—C34—H34B	76.9
C21—C20—C27	119.7 (2)	H34A—C34—H34B	109.5
C22—C21—C20	121.7 (2)	C32—C34—H34C	109.7
C22—C21—H21A	119.1	C33—C34—H34C	123.1
C20—C21—H21A	119.1	C35—C34—H34C	78.4
C17—C22—C21	121.2 (2)	H34A—C34—H34C	109.5
C17—C22—H22A	119.4	H34B—C34—H34C	109.5
C21—C22—H22A	119.4	C32—C34—H34	175.5
C24—C23—C14	112.4 (2)	C33—C34—H34	127.0
C24—C23—C25	108.8 (2)	C35—C34—H34	126.9
C14—C23—C25	110.5 (2)	H34A—C34—H34	66.6
C24—C23—C26	108.4 (2)	H34B—C34—H34	71.8
C14—C23—C26	108.3 (2)	H34C—C34—H34	73.3
C25—C23—C26	108.4 (2)	C31—C35—C32	66.4 (5)
C23—C24—H24A	109.5	C31—C35—C34	119.3 (6)
C23—C24—H24B	109.5	C32—C35—C34	52.9 (5)
H24A—C24—H24B	109.5	C31—C35—H35	120.4
C23—C24—H24C	109.5	C32—C35—H35	173.1
H24A—C24—H24C	109.5	C34—C35—H35	120.3
H24B—C24—H24C	109.5

N2—Zn1—N1—C1	178.9 (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—C4	0.1 (2)	C23—C14—C15—C16	172.1 (2)
N2ⁱ—Zn1—N1—C4	−179.9 (2)	C14—C15—C16—C11	0.9 (4)
N2ⁱ—Zn1—N1—N2	180.0	C12—C11—C16—C15	3.9 (4)
N1ⁱ—Zn1—N2—C9	−0.8 (2)	C5—C11—C16—C15	−169.3 (2)
N1—Zn1—N2—C9	179.2 (2)	C1ⁱ—C10—C17—C18	−103.8 (3)
N1ⁱ—Zn1—N2—C6	−179.6 (2)	C9—C10—C17—C18	77.2 (3)
N1—Zn1—N2—C6	0.4 (2)	C1ⁱ—C10—C17—C22	81.0 (3)
N1ⁱ—Zn1—N2—N1	180.0	C9—C10—C17—C22	−98.0 (3)
N1ⁱ—Zn1—N2—N1ⁱⁱⁱ	−15.84 (6)	C22—C17—C18—C19	0.8 (4)
N1—Zn1—N2—N1ⁱⁱⁱ	164.16 (6)	C10—C17—C18—C19	−174.5 (2)
C4—N1—N2—C6	0.37 (18)	C17—C18—C19—C20	−0.8 (4)
Zn1—N1—N2—C6	−179.72 (16)	C18—C19—C20—C21	0.5 (4)
C4—N1—N2—Zn1	−179.92 (16)	C18—C19—C20—C27	178.6 (2)
C4—N1—N2—N1ⁱⁱⁱ	155.51 (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—C10ⁱ	179.6 (2)	C18—C17—C22—C21	−0.7 (4)
Zn1—N1—C1—C10ⁱ	0.6 (4)	C10—C17—C22—C21	174.7 (2)
C4—N1—C1—C2	−0.2 (3)	C20—C21—C22—C17	0.5 (4)
Zn1—N1—C1—C2	−179.16 (16)	C13—C14—C23—C24	−0.5 (3)
N1—C1—C2—C3	0.3 (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—C25	60.8 (3)
C1—N1—C4—C5	−179.3 (2)	C13—C14—C23—C26	119.2 (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—C28	3.7 (4)
C1—N1—C4—C3	0.0 (3)	C21—C20—C27—C28	−178.3 (2)
Zn1—N1—C4—C3	178.98 (15)	C19—C20—C27—C30	124.5 (3)
N2—N1—C4—C3	179.06 (19)	C21—C20—C27—C30	−57.5 (3)
C2—C3—C4—N1	0.2 (3)	C19—C20—C27—C29	−116.6 (3)
C2—C3—C4—C5	179.4 (2)	C21—C20—C27—C29	61.4 (3)
N1—C4—C5—C6	0.0 (4)	C35—C31—C32—C34	1.4 (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—C11	1.3 (4)	C35—C31—C32—C31ⁱⁱ	178.1 (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—C31ⁱⁱ	0.0
N1—N2—C6—C5	−0.5 (2)	C33ⁱⁱ—C31—C32—C35	180.0 (6)
N1ⁱⁱⁱ—N2—C6—C5	−157.91 (17)	C32ⁱⁱ—C31—C32—C35	−178.1 (6)
C9—N2—C6—C7	0.5 (3)	C35—C31—C32—C32ⁱⁱ	178.1 (6)
Zn1—N2—C6—C7	179.57 (16)	C33ⁱⁱ—C31—C32—C32ⁱⁱ	−2.0 (6)
N1—N2—C6—C7	179.82 (19)	C34—C32—C33—C31ⁱⁱ	178.7 (4)
N1ⁱⁱⁱ—N2—C6—C7	22.4 (3)	C35—C32—C33—C31ⁱⁱ	176.6 (9)
C4—C5—C6—N2	0.6 (4)	C32ⁱⁱ—C32—C33—C31ⁱⁱ	2.1 (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—C33	1.5 (5)
C5—C6—C7—C8	−179.8 (2)	C35—C32—C34—C33	178.6 (6)
C6—C7—C8—C9	−0.3 (3)	C31—C32—C34—C33	177.4 (7)
C6—N2—C9—C10	179.0 (2)	C33—C32—C34—C35	−178.6 (6)
Zn1—N2—C9—C10	0.0 (3)	C31ⁱⁱ—C32—C34—C35	−177.0 (8)
N1ⁱⁱⁱ—N2—C9—C10	27.91 (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—C35	1.3 (5)
N1ⁱⁱⁱ—N2—C9—C8	−151.8 (3)	C31ⁱⁱ—C33—C34—C35	−0.4 (8)
C7—C8—C9—N2	0.7 (3)	C32ⁱⁱ—C31—C35—C32	2.5 (8)
C7—C8—C9—C10	−179.1 (2)	C32ⁱⁱ—C31—C35—C34	1.3 (10)
N2—C9—C10—C1ⁱ	1.0 (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—C12	81.3 (3)	C33—C32—C35—C34	2.0 (8)
C6—C5—C11—C16	74.7 (3)	C31ⁱⁱ—C32—C35—C34	173.3 (17)
C4—C5—C11—C16	−105.8 (3)	C31—C32—C35—C34	178.7 (5)
C16—C11—C12—C13	−4.5 (4)	C32ⁱⁱ—C32—C35—C34	177.1 (7)
C5—C11—C12—C13	168.6 (2)	C32—C34—C35—C31	1.4 (5)
C11—C12—C13—C14	0.2 (4)	C33—C34—C35—C31	0.3 (7)
C12—C13—C14—C15	4.6 (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.

Experimental details

Crystal data
Chemical formula	[Zn(C₆₀H₆₀N₄)]·C₇H₈
M_r	994.64
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	85
a, b, c (Å)	16.0277 (16), 9.5884 (14), 16.8714 (16)
β (°)	93.892 (8)
V (Å³)	2586.8 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.52
Crystal size (mm)	0.25 × 0.20 × 0.10

Data collection
Diffractometer	Oxford Diffraction Xcalibur
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14020, 4533, 3375
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.122, 1.05
No. of reflections	4533
No. of parameters	341
No. of restraints	93
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.37

Computer programs: CrysAlis CCD (Oxford Diffraction, 2002), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1990).

Selected geometric parameters (Å, º) top

Zn1—N2	2.024 (2)	Zn1—N1	2.054 (2)

N2—Zn1—N2ⁱ	180	N2—Zn1—N1	89.94 (8)
N2—Zn1—N1ⁱ	90.06 (8)

Symmetry code: (i) −x+1, −y+1, −z+1.

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