Crystal structure of {4-[10,15,20-tris­(4-meth­oxy­phen­yl)porphyrin-5-yl]benzyl 2-diazo­acetato}­zinc(II)

The structure of a zinc porphyrin bearing a diazo ester group at the periphery of the porphyrin ring leads to a coordination polymer featuring ZnN₄O square pyramids.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.051
• wR factor = 0.139
• Data-to-parameter ratio = 21.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          2 Check

Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z > Si, NonCentro ....     Please Do !
PLAT220_ALERT_2_C NonSolvent Resd 1  C   Ueq(max) / Ueq(min) Range        4.8 Ratio
PLAT220_ALERT_2_C NonSolvent Resd 1  N   Ueq(max) / Ueq(min) Range        4.1 Ratio
PLAT222_ALERT_3_C NonSolvent Resd 1  H   Uiso(max)/Uiso(min) Range        5.9 Ratio
PLAT242_ALERT_2_C Low    MainMol Ueq as Compared to Neighbors of        O47 Check
PLAT242_ALERT_2_C Low    MainMol Ueq as Compared to Neighbors of        C44 Check
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00786 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         10 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          1 Info
PLAT606_ALERT_4_G VERY LARGE Solvent Accessible VOID(S) in Structure        ! Info
PLAT794_ALERT_5_G Tentative Bond Valency for Zn1       (II)      .       1.88 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         14 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   9 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

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

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Computing details

Data collection: SAINT (Bruker, 2014); cell refinement: APEX3 (Bruker, 2015); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: SXGRAPH (Farrugia, 1999), Mercury (Macrae et al., 2008); software used to prepare material for publication: CRYSCALC (Roisnel, local program, 2019).

{4-[10,15,20-Tris(4-methoxyphenyl)porphyrin-5-yl]benzyl 2-diazoacetato}zinc(II)

Crystal data

[Zn(C50H36N6O5)]	F(000) = 896
Mr = 866.22	Dx = 1.089 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.8054 (8) Å	Cell parameters from 9886 reflections
b = 19.3938 (14) Å	θ = 2.5–27.4°
c = 12.7467 (10) Å	µ = 0.51 mm^−1
β = 98.523 (3)°	T = 150 K
V = 2641.7 (3) Å^3	Prism, red
Z = 2	0.32 × 0.30 × 0.10 mm

Data collection

D8 VENTURE Bruker AXS diffractometer	12068 independent reflections
Radiation source: Incoatec microfocus sealed tube	9931 reflections with I > 2σ(I)
Multilayer monochromator	Rint = 0.047
Detector resolution: 10.4167 pixels mm^-1	θmax = 27.5°, θmin = 2.1°
rotation images scans	h = −14→13
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −24→25
Tmin = 0.704, Tmax = 0.950	l = −16→16
28170 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.139	w = 1/[σ^2(Fo^2) + (0.0738P)^2 + 1.1085P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.024
12068 reflections	Δρmax = 0.43 e Å^−3
563 parameters	Δρmin = −0.42 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.033 (15)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
Zn1	0.00556 (5)	0.70060 (3)	0.62458 (4)	0.02718 (14)
N1	0.0900 (4)	0.7458 (2)	0.5081 (3)	0.0273 (9)
N2	−0.1436 (4)	0.6737 (2)	0.5139 (3)	0.0279 (9)
N3	−0.0613 (4)	0.6355 (2)	0.7323 (3)	0.0280 (9)
N4	0.1702 (3)	0.7083 (3)	0.7288 (3)	0.0264 (8)
C1	0.0353 (4)	0.7599 (3)	0.4074 (4)	0.0258 (10)
C2	−0.0846 (5)	0.7376 (3)	0.3602 (4)	0.0284 (10)
C3	−0.1656 (4)	0.6983 (3)	0.4102 (3)	0.0282 (9)
C4	−0.2887 (5)	0.6744 (3)	0.3615 (4)	0.0294 (10)
H4	−0.327042	0.683287	0.290868	0.035*
C5	−0.3383 (5)	0.6375 (3)	0.4341 (4)	0.0341 (12)
H5	−0.417616	0.615398	0.425012	0.041*
C6	−0.2463 (5)	0.6384 (3)	0.5294 (4)	0.0267 (10)
C7	−0.2652 (5)	0.6058 (2)	0.6254 (4)	0.0257 (10)
C8	−0.1758 (5)	0.6049 (3)	0.7185 (4)	0.0304 (11)
C9	−0.1968 (6)	0.5711 (3)	0.8157 (4)	0.0401 (13)
H9	−0.269308	0.546393	0.827774	0.048*
C10	−0.0913 (5)	0.5821 (3)	0.8860 (4)	0.0331 (12)
H10	−0.075922	0.565878	0.957105	0.040*
C11	−0.0068 (5)	0.6227 (3)	0.8337 (4)	0.0281 (10)
C12	0.1111 (5)	0.6462 (3)	0.8823 (4)	0.0309 (11)
C13	0.1928 (5)	0.6856 (2)	0.8307 (4)	0.0281 (11)
C14	0.3165 (5)	0.7062 (3)	0.8786 (4)	0.0345 (10)
H14	0.355695	0.696032	0.948623	0.041*
C15	0.3662 (5)	0.7428 (3)	0.8045 (4)	0.0327 (11)
H15	0.446606	0.763638	0.813239	0.039*
C16	0.2751 (4)	0.7442 (3)	0.7105 (4)	0.0266 (10)
C17	0.2948 (5)	0.7755 (2)	0.6138 (4)	0.0262 (10)
C18	0.2070 (5)	0.7756 (2)	0.5209 (4)	0.0263 (10)
C19	0.2248 (5)	0.8106 (3)	0.4230 (4)	0.0325 (11)
H19	0.296284	0.836265	0.410923	0.039*
C20	0.1203 (6)	0.7995 (3)	0.3528 (4)	0.0408 (13)
H20	0.105179	0.814796	0.281241	0.049*
C21	−0.1269 (5)	0.7562 (3)	0.2450 (4)	0.0305 (11)
C22	−0.1727 (9)	0.8212 (4)	0.2161 (5)	0.061 (2)
H22	−0.177863	0.854917	0.269352	0.073*
C23	−0.2109 (9)	0.8379 (4)	0.1107 (6)	0.067 (2)
H23	−0.236839	0.883653	0.092358	0.080*
C24	−0.2119 (6)	0.7893 (3)	0.0320 (4)	0.0434 (14)
C25	−0.1649 (6)	0.7242 (3)	0.0607 (5)	0.0475 (16)
H25	−0.162430	0.689600	0.008378	0.057*
C26	−0.1217 (5)	0.7103 (3)	0.1663 (4)	0.0395 (13)
H26	−0.086674	0.666223	0.184301	0.047*
O27	−0.2603 (5)	0.8092 (3)	−0.0664 (3)	0.0585 (13)
C28	−0.2763 (7)	0.7571 (4)	−0.1445 (5)	0.0555 (18)
H28A	−0.320784	0.717971	−0.118881	0.083*
H28B	−0.194202	0.741805	−0.159425	0.083*
H28C	−0.324992	0.775327	−0.209602	0.083*
C31	0.1521 (5)	0.6269 (3)	0.9941 (4)	0.0298 (10)
C32	0.1745 (6)	0.5584 (3)	1.0261 (5)	0.0419 (13)
H32	0.160518	0.522090	0.975640	0.050*
C33	0.2178 (6)	0.5436 (3)	1.1330 (4)	0.0380 (12)
H33	0.231397	0.496819	1.153829	0.046*
C34	0.2405 (6)	0.5930 (3)	1.2067 (5)	0.0424 (14)
C35	0.2166 (6)	0.6622 (3)	1.1777 (4)	0.0397 (13)
H35	0.229459	0.697573	1.229692	0.048*
C36	0.1744 (5)	0.6783 (3)	1.0732 (4)	0.0363 (12)
H36	0.159940	0.725241	1.053906	0.044*
O37	0.2872 (4)	0.5733 (2)	1.3082 (3)	0.0470 (10)
C38	0.3071 (7)	0.6249 (3)	1.3886 (5)	0.0478 (15)
H38A	0.363013	0.660543	1.367831	0.072*
H38B	0.345083	0.603894	1.455623	0.072*
H38C	0.226739	0.645802	1.397698	0.072*
C41	−0.3889 (5)	0.5724 (2)	0.6304 (4)	0.0260 (10)
C42	−0.4812 (6)	0.6063 (3)	0.6729 (5)	0.0387 (13)
H42	−0.465968	0.652103	0.697849	0.046*
C43	−0.5957 (6)	0.5764 (3)	0.6808 (6)	0.0464 (15)
H43	−0.658937	0.602078	0.707695	0.056*
C44	−0.6171 (5)	0.5084 (3)	0.6488 (5)	0.0353 (12)
C45	−0.5207 (7)	0.4725 (3)	0.6066 (5)	0.0497 (16)
H45	−0.532431	0.425747	0.585217	0.060*
C46	−0.4128 (6)	0.5049 (3)	0.5969 (6)	0.0454 (15)
H46	−0.350744	0.480710	0.566033	0.054*
O47	−0.7270 (4)	0.4728 (2)	0.6512 (5)	0.0628 (14)
C48	−0.8253 (10)	0.5098 (5)	0.6903 (13)	0.123 (5)
H48A	−0.827708	0.557236	0.663782	0.184*
H48B	−0.809986	0.510177	0.768063	0.184*
H48C	−0.905543	0.487177	0.665944	0.184*
C54	0.6527 (5)	0.8721 (3)	0.6153 (4)	0.0297 (11)
C55	0.5618 (5)	0.9019 (3)	0.6678 (5)	0.0357 (12)
H55	0.579464	0.944167	0.704745	0.043*
C56	0.4463 (6)	0.8711 (3)	0.6671 (5)	0.0385 (13)
H56	0.386237	0.892012	0.704379	0.046*
C51	0.4173 (5)	0.8096 (3)	0.6121 (4)	0.0271 (10)
C52	0.5070 (5)	0.7809 (2)	0.5572 (4)	0.0256 (10)
H52	0.488255	0.739651	0.517825	0.031*
C53	0.6239 (5)	0.8117 (3)	0.5589 (4)	0.0306 (11)
H53	0.684042	0.791255	0.521289	0.037*
O58	0.8581 (4)	0.89908 (19)	0.7153 (3)	0.0390 (9)
C59	0.9262 (5)	0.8416 (3)	0.7264 (5)	0.0342 (12)
C57	0.7751 (5)	0.9070 (3)	0.6121 (4)	0.0326 (11)
H57A	0.816041	0.886703	0.554810	0.039*
H57B	0.760818	0.956611	0.596421	0.039*
O60	0.9171 (4)	0.7974 (2)	0.6583 (3)	0.0410 (9)
C61	1.0062 (7)	0.8346 (3)	0.8270 (6)	0.0530 (18)
H61	1.059875	0.795791	0.839911	0.064*
N62	1.0053 (7)	0.8808 (4)	0.8992 (6)	0.076 (2)
N63	1.0095 (9)	0.9222 (5)	0.9599 (7)	0.109 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0255 (2)	0.0322 (3)	0.0238 (2)	−0.0034 (3)	0.00351 (18)	0.0022 (3)
N1	0.022 (2)	0.033 (2)	0.027 (2)	−0.0035 (17)	0.0065 (17)	0.0021 (17)
N2	0.031 (2)	0.033 (2)	0.019 (2)	−0.0007 (17)	0.0022 (17)	−0.0004 (16)
N3	0.027 (2)	0.031 (2)	0.024 (2)	−0.0103 (17)	0.0004 (17)	0.0036 (17)
N4	0.0224 (17)	0.031 (2)	0.0257 (18)	0.0005 (19)	0.0030 (14)	0.0083 (19)
C1	0.020 (2)	0.036 (3)	0.022 (2)	0.0022 (19)	0.0038 (18)	0.0054 (19)
C2	0.028 (2)	0.032 (2)	0.025 (2)	0.000 (2)	0.0030 (19)	0.001 (2)
C3	0.029 (2)	0.034 (2)	0.020 (2)	0.004 (3)	−0.0003 (16)	0.000 (2)
C4	0.025 (2)	0.039 (2)	0.023 (2)	−0.004 (2)	−0.0003 (19)	−0.001 (2)
C5	0.029 (3)	0.045 (3)	0.028 (3)	−0.001 (2)	0.005 (2)	−0.005 (2)
C6	0.029 (3)	0.031 (2)	0.021 (2)	0.000 (2)	0.0030 (19)	−0.0022 (18)
C7	0.029 (3)	0.027 (2)	0.023 (2)	−0.0018 (19)	0.0078 (19)	−0.0022 (18)
C8	0.036 (3)	0.034 (3)	0.022 (2)	−0.006 (2)	0.004 (2)	0.0011 (19)
C9	0.038 (3)	0.055 (3)	0.027 (3)	−0.016 (3)	0.002 (2)	0.008 (2)
C10	0.028 (3)	0.048 (3)	0.023 (3)	−0.011 (2)	0.001 (2)	0.010 (2)
C11	0.028 (3)	0.030 (2)	0.026 (2)	−0.005 (2)	0.004 (2)	0.0047 (19)
C12	0.029 (3)	0.038 (3)	0.024 (2)	0.001 (2)	−0.002 (2)	0.006 (2)
C13	0.025 (2)	0.032 (3)	0.028 (2)	−0.0006 (18)	0.0061 (19)	0.0038 (17)
C14	0.031 (2)	0.042 (3)	0.030 (2)	−0.004 (3)	0.0008 (18)	0.004 (3)
C15	0.026 (3)	0.042 (3)	0.029 (3)	−0.008 (2)	0.001 (2)	0.004 (2)
C16	0.020 (2)	0.032 (2)	0.029 (2)	−0.0027 (19)	0.0053 (19)	0.0004 (19)
C17	0.026 (2)	0.024 (2)	0.029 (3)	−0.0067 (18)	0.003 (2)	−0.0015 (18)
C18	0.026 (2)	0.031 (2)	0.022 (2)	−0.0014 (19)	0.0065 (19)	0.0029 (18)
C19	0.031 (3)	0.041 (3)	0.025 (3)	−0.010 (2)	0.003 (2)	0.005 (2)
C20	0.049 (3)	0.051 (3)	0.023 (3)	0.002 (3)	0.008 (2)	0.012 (2)
C21	0.028 (3)	0.039 (3)	0.025 (3)	0.000 (2)	0.005 (2)	0.006 (2)
C22	0.103 (6)	0.042 (3)	0.036 (3)	0.013 (4)	0.006 (4)	0.006 (3)
C23	0.102 (7)	0.043 (4)	0.049 (4)	0.018 (4)	−0.006 (4)	0.005 (3)
C24	0.046 (3)	0.060 (4)	0.025 (3)	0.005 (3)	0.010 (2)	0.019 (3)
C25	0.051 (4)	0.062 (4)	0.029 (3)	0.014 (3)	0.006 (3)	0.001 (2)
C26	0.044 (3)	0.038 (3)	0.035 (3)	0.017 (3)	−0.001 (2)	0.004 (2)
O27	0.065 (3)	0.079 (3)	0.029 (2)	0.018 (3)	0.002 (2)	0.012 (2)
C28	0.058 (4)	0.080 (5)	0.025 (3)	−0.002 (4)	−0.004 (3)	0.017 (3)
C31	0.028 (3)	0.034 (2)	0.027 (3)	−0.004 (2)	0.002 (2)	−0.001 (2)
C32	0.049 (3)	0.041 (3)	0.032 (3)	−0.002 (3)	−0.003 (3)	0.008 (2)
C33	0.052 (3)	0.033 (3)	0.029 (3)	−0.005 (2)	0.002 (2)	0.007 (2)
C34	0.040 (3)	0.054 (4)	0.030 (3)	−0.007 (3)	−0.003 (2)	0.009 (3)
C35	0.039 (3)	0.055 (3)	0.024 (3)	−0.008 (3)	0.001 (2)	−0.003 (2)
C36	0.037 (3)	0.042 (3)	0.029 (3)	0.001 (2)	0.000 (2)	0.006 (2)
O37	0.057 (3)	0.046 (2)	0.035 (2)	0.000 (2)	−0.002 (2)	0.0109 (18)
C38	0.048 (4)	0.048 (3)	0.043 (4)	−0.002 (3)	−0.009 (3)	−0.002 (3)
C41	0.030 (3)	0.027 (2)	0.021 (2)	−0.004 (2)	0.0042 (19)	−0.0008 (18)
C42	0.041 (3)	0.029 (3)	0.050 (4)	−0.008 (2)	0.017 (3)	−0.004 (2)
C43	0.032 (3)	0.039 (3)	0.072 (5)	−0.004 (2)	0.018 (3)	−0.004 (3)
C44	0.034 (3)	0.026 (2)	0.045 (3)	−0.013 (2)	0.005 (2)	0.004 (2)
C45	0.059 (4)	0.037 (3)	0.056 (4)	−0.017 (3)	0.018 (3)	−0.016 (3)
C46	0.037 (3)	0.042 (3)	0.059 (4)	−0.005 (3)	0.015 (3)	−0.019 (3)
O47	0.038 (2)	0.047 (2)	0.108 (4)	−0.015 (2)	0.025 (3)	−0.004 (3)
C48	0.079 (7)	0.052 (5)	0.259 (17)	−0.015 (5)	0.096 (9)	−0.032 (7)
C54	0.030 (3)	0.023 (2)	0.036 (3)	0.003 (2)	0.006 (2)	0.008 (2)
C55	0.036 (3)	0.033 (3)	0.039 (3)	−0.006 (2)	0.011 (2)	−0.013 (2)
C56	0.043 (3)	0.031 (3)	0.044 (3)	−0.003 (2)	0.015 (3)	−0.014 (2)
C51	0.024 (2)	0.034 (2)	0.022 (2)	−0.002 (2)	0.0009 (19)	−0.0019 (19)
C52	0.024 (2)	0.028 (2)	0.024 (2)	−0.0025 (19)	0.0008 (19)	−0.0022 (18)
C53	0.031 (3)	0.030 (2)	0.031 (3)	0.001 (2)	0.006 (2)	0.007 (2)
O58	0.041 (2)	0.0315 (19)	0.043 (2)	−0.0015 (16)	0.0017 (18)	−0.0020 (16)
C59	0.028 (3)	0.027 (2)	0.050 (3)	−0.003 (2)	0.015 (2)	−0.007 (2)
C57	0.026 (3)	0.032 (2)	0.040 (3)	−0.004 (2)	0.005 (2)	0.001 (2)
O60	0.044 (2)	0.037 (2)	0.042 (2)	0.0002 (17)	0.0075 (18)	−0.0055 (17)
C61	0.055 (4)	0.033 (3)	0.063 (4)	0.002 (3)	−0.017 (3)	−0.014 (3)
N62	0.079 (5)	0.080 (5)	0.066 (4)	0.030 (4)	0.001 (4)	−0.014 (4)
N63	0.109 (7)	0.118 (7)	0.089 (6)	0.034 (6)	−0.021 (5)	−0.066 (6)

Geometric parameters (Å, º)

Zn1—N2	2.046 (4)	C26—H26	0.9500
Zn1—N1	2.051 (4)	O27—C28	1.411 (9)
Zn1—N4	2.062 (4)	C28—H28A	0.9800
Zn1—N3	2.073 (4)	C28—H28B	0.9800
Zn1—O60^i	2.179 (4)	C28—H28C	0.9800
N1—C1	1.359 (6)	C31—C32	1.401 (8)
N1—C18	1.378 (6)	C31—C36	1.413 (8)
N2—C6	1.343 (7)	C32—C33	1.403 (8)
N2—C3	1.392 (6)	C32—H32	0.9500
N3—C8	1.359 (7)	C33—C34	1.340 (8)
N3—C11	1.360 (7)	C33—H33	0.9500
N4—C13	1.359 (6)	C34—O37	1.371 (7)
N4—C16	1.379 (6)	C34—C35	1.405 (9)
C1—C2	1.413 (7)	C35—C36	1.378 (8)
C1—C20	1.452 (7)	C35—H35	0.9500
C2—C3	1.385 (7)	C36—H36	0.9500
C2—C21	1.517 (7)	O37—C38	1.426 (8)
C3—C4	1.457 (7)	C38—H38A	0.9800
C4—C5	1.342 (8)	C38—H38B	0.9800
C4—H4	0.9500	C38—H38C	0.9800
C5—C6	1.451 (7)	C41—C42	1.372 (8)
C5—H5	0.9500	C41—C46	1.389 (8)
C6—C7	1.419 (7)	C42—C43	1.383 (8)
C7—C8	1.415 (7)	C42—H42	0.9500
C7—C41	1.495 (7)	C43—C44	1.390 (8)
C8—C9	1.449 (7)	C43—H43	0.9500
C9—C10	1.358 (8)	C44—O47	1.377 (7)
C9—H9	0.9500	C44—C45	1.423 (9)
C10—C11	1.443 (7)	C45—C46	1.345 (9)
C10—H10	0.9500	C45—H45	0.9500
C11—C12	1.407 (7)	C46—H46	0.9500
C12—C13	1.403 (7)	O47—C48	1.431 (10)
C12—C31	1.476 (7)	C48—H48A	0.9800
C13—C14	1.441 (7)	C48—H48B	0.9800
C14—C15	1.354 (7)	C48—H48C	0.9800
C14—H14	0.9500	C54—C53	1.384 (7)
C15—C16	1.434 (7)	C54—C55	1.394 (8)
C15—H15	0.9500	C54—C57	1.492 (7)
C16—C17	1.418 (7)	C55—C56	1.381 (8)
C17—C18	1.404 (7)	C55—H55	0.9500
C17—C51	1.483 (7)	C56—C51	1.397 (7)
C18—C19	1.458 (7)	C56—H56	0.9500
C19—C20	1.350 (8)	C51—C52	1.393 (7)
C19—H19	0.9500	C52—C53	1.395 (7)
C20—H20	0.9500	C52—H52	0.9500
C21—C26	1.347 (8)	C53—H53	0.9500
C21—C22	1.384 (8)	O58—C59	1.332 (6)
C22—C23	1.384 (10)	O58—C57	1.486 (7)
C22—H22	0.9500	C59—O60	1.213 (6)
C23—C24	1.374 (10)	C59—C61	1.443 (9)
C23—H23	0.9500	C57—H57A	0.9900
C24—O27	1.342 (7)	C57—H57B	0.9900
C24—C25	1.389 (9)	C61—N62	1.285 (10)
C25—C26	1.385 (8)	C61—H61	0.9500
C25—H25	0.9500	N62—N63	1.112 (10)
N2—Zn1—N1	89.95 (17)	C26—C25—H25	120.3
N2—Zn1—N4	168.25 (18)	C24—C25—H25	120.3
N1—Zn1—N4	90.10 (16)	C21—C26—C25	123.3 (5)
N2—Zn1—N3	89.15 (16)	C21—C26—H26	118.3
N1—Zn1—N3	167.43 (17)	C25—C26—H26	118.3
N4—Zn1—N3	88.25 (16)	C24—O27—C28	116.4 (5)
N2—Zn1—O60^i	91.84 (16)	O27—C28—H28A	109.5
N1—Zn1—O60^i	91.71 (16)	O27—C28—H28B	109.5
N4—Zn1—O60^i	99.90 (17)	H28A—C28—H28B	109.5
N3—Zn1—O60^i	100.85 (17)	O27—C28—H28C	109.5
C1—N1—C18	106.9 (4)	H28A—C28—H28C	109.5
C1—N1—Zn1	126.3 (3)	H28B—C28—H28C	109.5
C18—N1—Zn1	126.3 (3)	C32—C31—C36	117.2 (5)
C6—N2—C3	106.6 (4)	C32—C31—C12	122.4 (5)
C6—N2—Zn1	127.7 (3)	C36—C31—C12	120.4 (5)
C3—N2—Zn1	125.0 (3)	C31—C32—C33	119.7 (5)
C8—N3—C11	107.5 (4)	C31—C32—H32	120.2
C8—N3—Zn1	125.4 (3)	C33—C32—H32	120.2
C11—N3—Zn1	126.5 (3)	C34—C33—C32	122.3 (5)
C13—N4—C16	106.8 (4)	C34—C33—H33	118.8
C13—N4—Zn1	127.5 (3)	C32—C33—H33	118.8
C16—N4—Zn1	125.5 (3)	C33—C34—O37	117.8 (5)
N1—C1—C2	125.7 (4)	C33—C34—C35	119.4 (5)
N1—C1—C20	110.0 (4)	O37—C34—C35	122.8 (6)
C2—C1—C20	124.3 (5)	C36—C35—C34	119.5 (5)
C3—C2—C1	125.1 (5)	C36—C35—H35	120.2
C3—C2—C21	117.1 (4)	C34—C35—H35	120.2
C1—C2—C21	117.7 (4)	C35—C36—C31	121.8 (5)
C2—C3—N2	126.5 (4)	C35—C36—H36	119.1
C2—C3—C4	125.4 (4)	C31—C36—H36	119.1
N2—C3—C4	108.2 (4)	C34—O37—C38	118.5 (5)
C5—C4—C3	108.0 (5)	O37—C38—H38A	109.5
C5—C4—H4	126.0	O37—C38—H38B	109.5
C3—C4—H4	126.0	H38A—C38—H38B	109.5
C4—C5—C6	106.1 (5)	O37—C38—H38C	109.5
C4—C5—H5	127.0	H38A—C38—H38C	109.5
C6—C5—H5	127.0	H38B—C38—H38C	109.5
N2—C6—C7	125.6 (4)	C42—C41—C46	117.4 (5)
N2—C6—C5	111.2 (4)	C42—C41—C7	121.1 (4)
C7—C6—C5	123.3 (5)	C46—C41—C7	121.5 (5)
C8—C7—C6	124.2 (5)	C41—C42—C43	122.6 (5)
C8—C7—C41	117.6 (4)	C41—C42—H42	118.7
C6—C7—C41	118.2 (4)	C43—C42—H42	118.7
N3—C8—C7	126.8 (4)	C42—C43—C44	119.2 (6)
N3—C8—C9	110.0 (5)	C42—C43—H43	120.4
C7—C8—C9	123.3 (5)	C44—C43—H43	120.4
C10—C9—C8	105.7 (5)	O47—C44—C43	125.1 (6)
C10—C9—H9	127.2	O47—C44—C45	116.5 (5)
C8—C9—H9	127.2	C43—C44—C45	118.4 (5)
C9—C10—C11	107.9 (5)	C46—C45—C44	120.0 (5)
C9—C10—H10	126.1	C46—C45—H45	120.0
C11—C10—H10	126.1	C44—C45—H45	120.0
N3—C11—C12	126.6 (4)	C45—C46—C41	122.4 (6)
N3—C11—C10	108.9 (4)	C45—C46—H46	118.8
C12—C11—C10	124.5 (5)	C41—C46—H46	118.8
C13—C12—C11	124.2 (5)	C44—O47—C48	116.4 (6)
C13—C12—C31	118.1 (5)	O47—C48—H48A	109.5
C11—C12—C31	117.8 (5)	O47—C48—H48B	109.5
N4—C13—C12	126.0 (5)	H48A—C48—H48B	109.5
N4—C13—C14	109.8 (4)	O47—C48—H48C	109.5
C12—C13—C14	124.2 (5)	H48A—C48—H48C	109.5
C15—C14—C13	106.8 (4)	H48B—C48—H48C	109.5
C15—C14—H14	126.6	C53—C54—C55	118.7 (5)
C13—C14—H14	126.6	C53—C54—C57	120.1 (5)
C14—C15—C16	107.4 (5)	C55—C54—C57	121.0 (5)
C14—C15—H15	126.3	C56—C55—C54	121.2 (5)
C16—C15—H15	126.3	C56—C55—H55	119.4
N4—C16—C17	126.6 (4)	C54—C55—H55	119.4
N4—C16—C15	109.2 (4)	C55—C56—C51	120.5 (5)
C17—C16—C15	124.2 (4)	C55—C56—H56	119.7
C18—C17—C16	124.4 (4)	C51—C56—H56	119.7
C18—C17—C51	118.7 (4)	C52—C51—C56	118.2 (5)
C16—C17—C51	117.0 (4)	C52—C51—C17	121.3 (4)
N1—C18—C17	126.4 (4)	C56—C51—C17	120.5 (5)
N1—C18—C19	109.2 (4)	C51—C52—C53	121.1 (5)
C17—C18—C19	124.4 (5)	C51—C52—H52	119.4
C20—C19—C18	106.8 (5)	C53—C52—H52	119.4
C20—C19—H19	126.6	C54—C53—C52	120.3 (5)
C18—C19—H19	126.6	C54—C53—H53	119.9
C19—C20—C1	107.0 (5)	C52—C53—H53	119.9
C19—C20—H20	126.5	C59—O58—C57	115.6 (4)
C1—C20—H20	126.5	O60—C59—O58	122.0 (5)
C26—C21—C22	117.1 (5)	O60—C59—C61	123.0 (5)
C26—C21—C2	121.6 (5)	O58—C59—C61	114.9 (5)
C22—C21—C2	121.3 (5)	O58—C57—C54	110.5 (4)
C23—C22—C21	120.9 (6)	O58—C57—H57A	109.6
C23—C22—H22	119.5	C54—C57—H57A	109.6
C21—C22—H22	119.5	O58—C57—H57B	109.6
C24—C23—C22	121.2 (6)	C54—C57—H57B	109.6
C24—C23—H23	119.4	H57A—C57—H57B	108.1
C22—C23—H23	119.4	C59—O60—Zn1^ii	139.3 (4)
O27—C24—C23	116.5 (6)	N62—C61—C59	120.3 (6)
O27—C24—C25	125.7 (6)	N62—C61—H61	119.9
C23—C24—C25	117.8 (5)	C59—C61—H61	119.9
C26—C25—C24	119.4 (6)	N63—N62—C61	176.5 (11)
C18—N1—C1—C2	178.4 (5)	C51—C17—C18—C19	−3.6 (7)
Zn1—N1—C1—C2	−9.3 (7)	N1—C18—C19—C20	−1.7 (6)
C18—N1—C1—C20	0.7 (6)	C17—C18—C19—C20	−179.4 (5)
Zn1—N1—C1—C20	173.0 (4)	C18—C19—C20—C1	2.0 (6)
N1—C1—C2—C3	0.9 (8)	N1—C1—C20—C19	−1.8 (6)
C20—C1—C2—C3	178.3 (5)	C2—C1—C20—C19	−179.5 (5)
N1—C1—C2—C21	−177.4 (5)	C3—C2—C21—C26	−77.8 (7)
C20—C1—C2—C21	0.0 (8)	C1—C2—C21—C26	100.6 (6)
C1—C2—C3—N2	−0.6 (9)	C3—C2—C21—C22	102.3 (7)
C21—C2—C3—N2	177.7 (5)	C1—C2—C21—C22	−79.3 (8)
C1—C2—C3—C4	−179.2 (5)	C26—C21—C22—C23	−0.1 (12)
C21—C2—C3—C4	−0.9 (8)	C2—C21—C22—C23	179.9 (7)
C6—N2—C3—C2	179.9 (5)	C21—C22—C23—C24	4.0 (14)
Zn1—N2—C3—C2	8.7 (8)	C22—C23—C24—O27	174.6 (8)
C6—N2—C3—C4	−1.2 (6)	C22—C23—C24—C25	−4.5 (12)
Zn1—N2—C3—C4	−172.5 (3)	O27—C24—C25—C26	−177.7 (6)
C2—C3—C4—C5	179.5 (5)	C23—C24—C25—C26	1.3 (10)
N2—C3—C4—C5	0.6 (6)	C22—C21—C26—C25	−3.2 (10)
C3—C4—C5—C6	0.2 (6)	C2—C21—C26—C25	176.9 (6)
C3—N2—C6—C7	−178.5 (5)	C24—C25—C26—C21	2.6 (10)
Zn1—N2—C6—C7	−7.5 (7)	C23—C24—O27—C28	−172.0 (7)
C3—N2—C6—C5	1.4 (6)	C25—C24—O27—C28	7.0 (10)
Zn1—N2—C6—C5	172.4 (3)	C13—C12—C31—C32	−114.4 (6)
C4—C5—C6—N2	−1.0 (6)	C11—C12—C31—C32	64.5 (7)
C4—C5—C6—C7	178.9 (5)	C13—C12—C31—C36	63.4 (7)
N2—C6—C7—C8	−1.3 (8)	C11—C12—C31—C36	−117.7 (6)
C5—C6—C7—C8	178.8 (5)	C36—C31—C32—C33	−0.2 (8)
N2—C6—C7—C41	176.3 (5)	C12—C31—C32—C33	177.7 (5)
C5—C6—C7—C41	−3.6 (7)	C31—C32—C33—C34	−0.9 (10)
C11—N3—C8—C7	179.2 (5)	C32—C33—C34—O37	−177.5 (6)
Zn1—N3—C8—C7	6.9 (8)	C32—C33—C34—C35	2.2 (10)
C11—N3—C8—C9	0.3 (6)	C33—C34—C35—C36	−2.3 (9)
Zn1—N3—C8—C9	−171.9 (4)	O37—C34—C35—C36	177.4 (6)
C6—C7—C8—N3	1.5 (8)	C34—C35—C36—C31	1.2 (9)
C41—C7—C8—N3	−176.1 (5)	C32—C31—C36—C35	0.1 (8)
C6—C7—C8—C9	−179.8 (5)	C12—C31—C36—C35	−177.9 (5)
C41—C7—C8—C9	2.6 (8)	C33—C34—O37—C38	−177.4 (6)
N3—C8—C9—C10	−0.6 (7)	C35—C34—O37—C38	2.9 (9)
C7—C8—C9—C10	−179.5 (5)	C8—C7—C41—C42	81.1 (7)
C8—C9—C10—C11	0.6 (7)	C6—C7—C41—C42	−96.7 (6)
C8—N3—C11—C12	−178.4 (5)	C8—C7—C41—C46	−95.9 (6)
Zn1—N3—C11—C12	−6.3 (8)	C6—C7—C41—C46	86.3 (7)
C8—N3—C11—C10	0.1 (6)	C46—C41—C42—C43	−1.5 (9)
Zn1—N3—C11—C10	172.2 (4)	C7—C41—C42—C43	−178.6 (6)
C9—C10—C11—N3	−0.5 (7)	C41—C42—C43—C44	2.8 (11)
C9—C10—C11—C12	178.0 (5)	C42—C43—C44—O47	−179.2 (6)
N3—C11—C12—C13	−1.9 (9)	C42—C43—C44—C45	−1.5 (10)
C10—C11—C12—C13	179.9 (5)	O47—C44—C45—C46	176.9 (7)
N3—C11—C12—C31	179.4 (5)	C43—C44—C45—C46	−1.0 (10)
C10—C11—C12—C31	1.1 (8)	C44—C45—C46—C41	2.4 (11)
C16—N4—C13—C12	−179.4 (5)	C42—C41—C46—C45	−1.2 (10)
Zn1—N4—C13—C12	6.5 (8)	C7—C41—C46—C45	175.9 (6)
C16—N4—C13—C14	−1.2 (6)	C43—C44—O47—C48	−0.2 (12)
Zn1—N4—C13—C14	−175.3 (4)	C45—C44—O47—C48	−177.9 (9)
C11—C12—C13—N4	1.8 (8)	C53—C54—C55—C56	2.2 (9)
C31—C12—C13—N4	−179.5 (5)	C57—C54—C55—C56	177.2 (5)
C11—C12—C13—C14	−176.1 (5)	C54—C55—C56—C51	−1.0 (9)
C31—C12—C13—C14	2.6 (8)	C55—C56—C51—C52	−0.8 (9)
N4—C13—C14—C15	1.3 (7)	C55—C56—C51—C17	178.2 (5)
C12—C13—C14—C15	179.5 (5)	C18—C17—C51—C52	−71.5 (6)
C13—C14—C15—C16	−0.9 (6)	C16—C17—C51—C52	108.0 (6)
C13—N4—C16—C17	178.1 (5)	C18—C17—C51—C56	109.5 (6)
Zn1—N4—C16—C17	−7.6 (8)	C16—C17—C51—C56	−71.0 (7)
C13—N4—C16—C15	0.7 (6)	C56—C51—C52—C53	1.5 (8)
Zn1—N4—C16—C15	174.9 (4)	C17—C51—C52—C53	−177.6 (5)
C14—C15—C16—N4	0.2 (6)	C55—C54—C53—C52	−1.5 (8)
C14—C15—C16—C17	−177.4 (5)	C57—C54—C53—C52	−176.6 (5)
N4—C16—C17—C18	1.4 (8)	C51—C52—C53—C54	−0.3 (8)
C15—C16—C17—C18	178.5 (5)	C57—O58—C59—O60	−2.9 (7)
N4—C16—C17—C51	−178.1 (5)	C57—O58—C59—C61	180.0 (5)
C15—C16—C17—C51	−1.0 (7)	C59—O58—C57—C54	86.2 (5)
C1—N1—C18—C17	178.2 (5)	C53—C54—C57—O58	−108.5 (5)
Zn1—N1—C18—C17	6.0 (7)	C55—C54—C57—O58	76.6 (6)
C1—N1—C18—C19	0.5 (6)	O58—C59—O60—Zn1^ii	174.5 (4)
Zn1—N1—C18—C19	−171.7 (3)	C61—C59—O60—Zn1^ii	−8.5 (9)
C16—C17—C18—N1	−0.4 (8)	O60—C59—C61—N62	−174.9 (7)
C51—C17—C18—N1	179.1 (5)	O58—C59—C61—N62	2.2 (10)
C16—C17—C18—C19	176.9 (5)

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