Download citation
Download citation
link to html
Studying the axial ligation behavior of metalloporphyrins with nitro­genous bases helps to better understand not only the biological function of heme-based protein systems, but also the catalytic properties of porphyrin-based reaction sites in other biomimetic synthetic support environments. Unlike iron porphyrin complexes, little is known about the axial ligation behavior of Mn porphyrins, particularly in the solid state with Mn in the +3 oxidation state. Here, we present the syntheses and crystal and mol­ecular structures of three new high-spin manganese(III) porphyrin complexes with the different amine-based axial ligands imidazole (im), piperidine (pip), and 1,4-di­aza­bicyclo­[2.2.2]octane (DABCO), namely bis­(imidazole)(5,10,15,20-tetra­phenyl­porphyrinato)mangan­ese(III) chloride chloro­form disolvate, [Mn(C44H28N4)(C3H4N2)2]Cl·2CHCl3 or [Mn(TPP)(im)2]Cl·2CHCl3 (TPP = 5,10,15,20-tetra­phenyl­porphyrin), (I), bis­(piperidine)(5,10,15,20-tetra­phenyl­porphyrinato)manganese(III) chloride, [Mn(C44H28N4)(C5H11N)2]Cl or [Mn(TPP)(pip)2]Cl, (II), and chlorido­(1,4-di­aza­bicyclo­[2.2.2]octa­ne)(5,10,15,20-tetra­phenyl­porphyrin)manganese(III)–1,4-di­aza­bicyclo­[2.2.2]octa­ne–toluene–water (4/4/4/1), [Mn(C44H28N4)Cl(C6H12N2)]·C6H12N2·C7H8·0.25H2O or [Mn(TPP)Cl(DABCO)]·(DABCO)·(toluene)·0.25H2O, (IV). A fourth complex, chlorido­(pyridine)(5,10,15,20-tetra­phenyl­porphryinato)manganese(III) pyridine disolvate, [Mn(C44H28N4)Cl(C5H5N)]·2C5H5N or [Mn(TPP)Cl(py)]·2(py), (III), acquired using different crystallization methods from published data, is also reported and compared to the previous structures.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619001232/jx3027sup1.cif
Contains datablocks I_Imidazole, II_Piperidine, III_Pyridine, IV_DABCO, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619001232/jx3027I_Imidazolesup2.hkl
Contains datablock I_Imidazole

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619001232/jx3027II_Piperidinesup3.hkl
Contains datablock II_Piperidine

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619001232/jx3027III_Pyridinesup4.hkl
Contains datablock III_Pyridine

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619001232/jx3027IV_DABCOsup5.hkl
Contains datablock IV_DABCO

CCDC references: 1860177; 1860175; 1860171; 1860170

Computing details top

For all structures, data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 (Bruker, 2006); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Bis(imidazole)(5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride chloroform disolvate (I_Imidazole) top
Crystal data top
[Mn(C44H28N4)(C3H4N2)2]Cl·2CHCl3Z = 2
Mr = 1077.99F(000) = 1100
Triclinic, P1Dx = 1.452 Mg m3
a = 11.3475 (2) ÅCu Kα radiation, λ = 1.54178 Å
b = 14.2479 (3) ÅCell parameters from 9842 reflections
c = 16.4138 (4) Åθ = 2.7–68.9°
α = 92.510 (1)°µ = 6.03 mm1
β = 99.529 (1)°T = 100 K
γ = 108.699 (1)°Block, black
V = 2465.63 (9) Å30.43 × 0.31 × 0.22 mm
Data collection top
Bruker SMART CCD APEXII area-detector
diffractometer
8162 independent reflections
Radiation source: fine-focus sealed tube7785 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
φ and ω scansθmax = 66.6°, θmin = 2.7°
Absorption correction: numerical
(SADABS; Krause et al., 2015)
h = 1313
Tmin = 0.168, Tmax = 0.447k = 1617
23350 measured reflectionsl = 1919
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)] = 0.043H-atom parameters constrained
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.0545P)2 + 3.7406P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
8162 reflectionsΔρmax = 1.24 e Å3
614 parametersΔρmin = 1.02 e Å3
0 restraintsExtinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00056 (9)
Special details top

Experimental. Crystal mounted on a Cryoloop using Paratone-N.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Mn10.61658 (3)0.75403 (3)0.23878 (2)0.01308 (11)
Cl10.71735 (6)0.26873 (4)0.20734 (4)0.02189 (15)
Cl50.84687 (7)0.31994 (5)0.47894 (4)0.03372 (17)
Cl70.81761 (11)0.50249 (6)0.42514 (5)0.0589 (3)
Cl60.99856 (10)0.42242 (10)0.36517 (6)0.0815 (4)
Cl31.04132 (11)0.87957 (8)0.74718 (8)0.0683 (3)
Cl20.85271 (9)0.69728 (7)0.76379 (9)0.0731 (4)
Cl41.03780 (13)0.81017 (12)0.90833 (7)0.0862 (4)
N20.49991 (18)0.75920 (14)0.13354 (12)0.0149 (4)
N40.73304 (19)0.75133 (15)0.34578 (12)0.0160 (4)
N30.76885 (18)0.81946 (15)0.18701 (12)0.0158 (4)
N70.62805 (19)0.90946 (15)0.28887 (13)0.0178 (4)
N10.46442 (19)0.68853 (15)0.28989 (12)0.0159 (4)
N50.6077 (2)0.60020 (15)0.18634 (13)0.0195 (4)
N60.6432 (2)0.45814 (16)0.17264 (14)0.0263 (5)
H60.67780.41160.18220.032*
N80.6573 (2)1.06948 (16)0.29042 (15)0.0272 (5)
H80.65971.12720.27240.033*
C260.6751 (2)0.89127 (18)0.02842 (15)0.0171 (5)
C60.5358 (2)0.79889 (17)0.06254 (14)0.0153 (5)
C150.6970 (2)0.72608 (18)0.42076 (15)0.0172 (5)
C30.3694 (2)0.71654 (17)0.11515 (15)0.0158 (5)
C160.5732 (2)0.68833 (17)0.43352 (15)0.0171 (5)
C170.4658 (2)0.66810 (17)0.37143 (15)0.0174 (5)
C10.3391 (2)0.65538 (18)0.25074 (15)0.0175 (5)
C70.6594 (2)0.84512 (17)0.05122 (14)0.0163 (5)
C80.7672 (2)0.85280 (18)0.10910 (15)0.0174 (5)
C120.8634 (2)0.79152 (18)0.36229 (15)0.0179 (5)
C40.3244 (2)0.72934 (18)0.03097 (15)0.0188 (5)
H40.23870.70570.00260.023*
C20.2928 (2)0.66728 (18)0.16903 (15)0.0174 (5)
C50.4258 (2)0.78106 (18)0.00095 (15)0.0169 (5)
H50.42440.80170.05530.020*
C470.6232 (3)0.98242 (19)0.24380 (17)0.0247 (6)
H470.59830.97430.18500.030*
C200.1524 (2)0.6255 (2)0.13778 (15)0.0219 (5)
C380.5535 (2)0.67505 (19)0.52093 (15)0.0194 (5)
C100.9728 (2)0.8942 (2)0.16775 (16)0.0227 (5)
H101.06280.91880.17810.027*
C110.8943 (2)0.84568 (18)0.22446 (15)0.0183 (5)
C180.3385 (2)0.62031 (18)0.38290 (15)0.0202 (5)
H180.31340.59880.43330.024*
C90.8951 (2)0.8985 (2)0.09725 (16)0.0221 (5)
H90.92020.92650.04880.027*
C440.6782 (3)0.54772 (19)0.21640 (16)0.0237 (6)
H440.74550.57030.26320.028*
C0120.9396 (2)0.83396 (19)0.30606 (15)0.0187 (5)
C321.0799 (2)0.8778 (2)0.33851 (15)0.0199 (5)
C390.5884 (3)0.6041 (2)0.56547 (16)0.0249 (6)
H390.62310.56060.53980.030*
C140.8084 (2)0.75014 (19)0.48440 (15)0.0213 (5)
H140.81050.74030.54140.026*
C331.1309 (3)0.9760 (2)0.37447 (17)0.0258 (6)
H331.07661.01400.37850.031*
C130.9095 (2)0.78917 (19)0.44854 (16)0.0215 (5)
H130.99590.81120.47560.026*
C480.6690 (3)0.9537 (2)0.36959 (17)0.0264 (6)
H480.68230.92000.41710.032*
C270.6559 (3)0.9819 (2)0.03807 (16)0.0237 (6)
H270.63731.01580.00670.028*
C310.7041 (3)0.8432 (2)0.09420 (16)0.0244 (6)
H310.71890.78170.08800.029*
C430.5016 (2)0.7374 (2)0.55957 (16)0.0225 (5)
H430.47450.78430.52910.027*
C250.0827 (3)0.6876 (2)0.11540 (17)0.0284 (6)
H250.12390.75760.12000.034*
C290.6900 (2)0.9744 (2)0.17855 (16)0.0251 (6)
H290.69341.00220.23000.030*
C300.7115 (3)0.8853 (2)0.16916 (16)0.0276 (6)
H300.73140.85240.21390.033*
C420.4893 (3)0.7313 (2)0.64198 (17)0.0290 (6)
H420.45610.77530.66830.035*
C351.3393 (3)0.9636 (2)0.39936 (16)0.0269 (6)
H351.42770.99290.42010.032*
C371.1602 (3)0.8230 (2)0.33359 (17)0.0265 (6)
H371.12670.75580.30930.032*
C190.2609 (2)0.61147 (19)0.30899 (16)0.0206 (5)
H190.17120.58180.29760.025*
C460.5239 (3)0.5405 (2)0.11954 (19)0.0322 (7)
H460.46060.55830.08450.039*
C410.5252 (3)0.6615 (2)0.68571 (17)0.0318 (7)
H410.51740.65780.74230.038*
C341.2593 (3)1.0187 (2)0.40433 (17)0.0290 (6)
H341.29301.08600.42830.035*
C280.6636 (3)1.0233 (2)0.11298 (17)0.0273 (6)
H280.65061.08550.11910.033*
C210.0906 (3)0.5233 (2)0.13120 (17)0.0309 (6)
H210.13760.48000.14590.037*
C400.5726 (3)0.5968 (2)0.64761 (17)0.0307 (6)
H400.59440.54720.67750.037*
C450.5449 (3)0.4526 (2)0.11112 (19)0.0314 (6)
H450.49980.39800.07030.038*
C361.2901 (3)0.8660 (2)0.36418 (18)0.0291 (6)
H361.34470.82810.36080.035*
C240.0477 (3)0.6475 (3)0.08616 (18)0.0371 (7)
H240.09520.69010.07050.045*
C490.6875 (3)1.0525 (2)0.37068 (18)0.0292 (6)
H490.71591.10030.41810.035*
C230.1075 (3)0.5459 (3)0.08009 (18)0.0407 (8)
H230.19620.51860.05980.049*
C220.0396 (3)0.4841 (3)0.10318 (19)0.0409 (8)
H220.08170.41430.10000.049*
C501.0095 (3)0.7741 (3)0.8023 (2)0.0419 (8)
H501.06760.73690.79170.050*
C510.8508 (3)0.3941 (2)0.39582 (19)0.0407 (8)
H510.78350.35520.34790.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0131 (2)0.0142 (2)0.01221 (19)0.00489 (15)0.00221 (14)0.00284 (15)
Cl10.0307 (3)0.0188 (3)0.0172 (3)0.0116 (2)0.0004 (2)0.0018 (2)
Cl50.0334 (4)0.0333 (4)0.0349 (4)0.0129 (3)0.0045 (3)0.0013 (3)
Cl70.0950 (7)0.0317 (4)0.0341 (4)0.0130 (4)0.0149 (4)0.0031 (3)
Cl60.0509 (6)0.1128 (9)0.0390 (5)0.0325 (6)0.0203 (4)0.0172 (5)
Cl30.0716 (7)0.0542 (6)0.0908 (8)0.0306 (5)0.0227 (6)0.0277 (6)
Cl20.0357 (5)0.0450 (5)0.1375 (11)0.0153 (4)0.0120 (6)0.0007 (6)
Cl40.0984 (9)0.1468 (12)0.0482 (6)0.0889 (9)0.0132 (6)0.0091 (7)
N20.0159 (10)0.0147 (9)0.0144 (9)0.0058 (8)0.0021 (8)0.0017 (8)
N40.0168 (10)0.0173 (10)0.0152 (10)0.0071 (8)0.0029 (8)0.0029 (8)
N30.0150 (10)0.0182 (10)0.0144 (10)0.0059 (8)0.0018 (8)0.0027 (8)
N70.0185 (10)0.0161 (10)0.0185 (10)0.0060 (8)0.0026 (8)0.0016 (8)
N10.0169 (10)0.0162 (10)0.0142 (10)0.0047 (8)0.0028 (8)0.0035 (8)
N50.0251 (11)0.0163 (10)0.0190 (10)0.0087 (9)0.0056 (9)0.0027 (8)
N60.0393 (14)0.0187 (11)0.0302 (12)0.0162 (10)0.0168 (10)0.0099 (10)
N80.0378 (14)0.0147 (10)0.0318 (13)0.0110 (10)0.0089 (10)0.0055 (9)
C260.0129 (11)0.0212 (12)0.0158 (12)0.0031 (10)0.0036 (9)0.0040 (10)
C60.0198 (12)0.0136 (11)0.0131 (11)0.0065 (10)0.0025 (9)0.0008 (9)
C150.0230 (13)0.0162 (11)0.0144 (11)0.0091 (10)0.0032 (10)0.0032 (9)
C30.0164 (12)0.0141 (11)0.0156 (11)0.0043 (10)0.0016 (9)0.0005 (9)
C160.0229 (13)0.0146 (11)0.0156 (12)0.0079 (10)0.0042 (10)0.0044 (9)
C170.0216 (13)0.0140 (11)0.0180 (12)0.0067 (10)0.0059 (10)0.0032 (10)
C10.0177 (12)0.0152 (11)0.0187 (12)0.0038 (10)0.0040 (10)0.0021 (10)
C70.0189 (12)0.0167 (11)0.0152 (11)0.0079 (10)0.0041 (9)0.0018 (10)
C80.0183 (12)0.0183 (12)0.0169 (12)0.0067 (10)0.0053 (10)0.0027 (10)
C120.0171 (12)0.0192 (12)0.0184 (12)0.0090 (10)0.0006 (9)0.0009 (10)
C40.0172 (12)0.0197 (12)0.0165 (12)0.0046 (10)0.0012 (10)0.0000 (10)
C20.0160 (12)0.0160 (11)0.0181 (12)0.0037 (10)0.0015 (9)0.0007 (10)
C50.0188 (12)0.0181 (12)0.0135 (11)0.0060 (10)0.0024 (9)0.0020 (9)
C470.0319 (15)0.0214 (13)0.0227 (13)0.0124 (12)0.0029 (11)0.0024 (11)
C200.0181 (13)0.0296 (14)0.0144 (11)0.0029 (11)0.0029 (10)0.0031 (10)
C380.0189 (12)0.0195 (12)0.0161 (12)0.0016 (10)0.0025 (10)0.0017 (10)
C100.0149 (12)0.0305 (14)0.0223 (13)0.0062 (11)0.0043 (10)0.0048 (11)
C110.0161 (12)0.0198 (12)0.0198 (12)0.0072 (10)0.0031 (10)0.0033 (10)
C180.0228 (13)0.0195 (12)0.0181 (12)0.0049 (10)0.0068 (10)0.0053 (10)
C90.0188 (13)0.0282 (14)0.0191 (12)0.0059 (11)0.0058 (10)0.0074 (11)
C440.0312 (15)0.0231 (13)0.0223 (13)0.0144 (12)0.0081 (11)0.0070 (11)
C0120.0165 (12)0.0205 (12)0.0198 (12)0.0083 (10)0.0014 (10)0.0004 (10)
C320.0165 (12)0.0282 (13)0.0147 (11)0.0073 (11)0.0014 (9)0.0059 (10)
C390.0305 (15)0.0213 (13)0.0194 (13)0.0057 (11)0.0007 (11)0.0021 (11)
C140.0254 (14)0.0253 (13)0.0145 (11)0.0107 (11)0.0022 (10)0.0052 (10)
C330.0241 (14)0.0278 (14)0.0265 (14)0.0107 (12)0.0037 (11)0.0016 (12)
C130.0192 (13)0.0260 (13)0.0191 (12)0.0097 (11)0.0017 (10)0.0030 (11)
C480.0362 (16)0.0228 (13)0.0200 (13)0.0102 (12)0.0037 (11)0.0015 (11)
C270.0285 (14)0.0239 (13)0.0210 (13)0.0095 (11)0.0089 (11)0.0043 (11)
C310.0300 (14)0.0248 (13)0.0217 (13)0.0112 (12)0.0089 (11)0.0039 (11)
C430.0199 (13)0.0248 (13)0.0210 (13)0.0051 (11)0.0038 (10)0.0024 (11)
C250.0193 (13)0.0368 (16)0.0267 (14)0.0073 (12)0.0027 (11)0.0010 (12)
C290.0183 (13)0.0351 (15)0.0191 (12)0.0039 (11)0.0039 (10)0.0102 (11)
C300.0291 (15)0.0363 (15)0.0180 (13)0.0101 (13)0.0080 (11)0.0013 (12)
C420.0261 (14)0.0341 (15)0.0238 (14)0.0050 (12)0.0080 (11)0.0023 (12)
C350.0179 (13)0.0376 (16)0.0202 (13)0.0036 (12)0.0002 (10)0.0082 (12)
C370.0209 (13)0.0284 (14)0.0301 (14)0.0096 (12)0.0018 (11)0.0024 (12)
C190.0173 (12)0.0212 (12)0.0211 (12)0.0027 (10)0.0044 (10)0.0036 (10)
C460.0344 (16)0.0275 (15)0.0333 (15)0.0154 (13)0.0048 (12)0.0068 (12)
C410.0325 (16)0.0366 (16)0.0178 (13)0.0017 (13)0.0079 (11)0.0016 (12)
C340.0276 (15)0.0297 (15)0.0239 (14)0.0036 (12)0.0016 (11)0.0009 (12)
C280.0306 (15)0.0265 (14)0.0274 (14)0.0108 (12)0.0080 (11)0.0116 (12)
C210.0278 (15)0.0310 (15)0.0241 (14)0.0016 (12)0.0003 (12)0.0056 (12)
C400.0392 (17)0.0252 (14)0.0212 (13)0.0032 (13)0.0012 (12)0.0081 (11)
C450.0356 (16)0.0219 (14)0.0363 (16)0.0097 (12)0.0075 (13)0.0043 (12)
C360.0189 (13)0.0373 (16)0.0334 (15)0.0131 (12)0.0026 (11)0.0082 (13)
C240.0200 (14)0.060 (2)0.0296 (15)0.0131 (14)0.0022 (12)0.0028 (15)
C490.0356 (16)0.0219 (13)0.0269 (14)0.0077 (12)0.0025 (12)0.0041 (11)
C230.0158 (14)0.069 (2)0.0236 (14)0.0042 (15)0.0020 (11)0.0035 (15)
C220.0320 (17)0.0433 (18)0.0269 (15)0.0121 (15)0.0022 (13)0.0070 (14)
C500.0363 (18)0.0446 (19)0.051 (2)0.0232 (15)0.0044 (15)0.0067 (16)
C510.0429 (19)0.0390 (17)0.0236 (14)0.0060 (15)0.0025 (13)0.0046 (13)
Geometric parameters (Å, º) top
Mn1—N22.015 (2)C10—C111.440 (4)
Mn1—N12.018 (2)C10—H100.9500
Mn1—N32.025 (2)C11—C0121.390 (4)
Mn1—N42.025 (2)C18—C191.351 (4)
Mn1—N72.284 (2)C18—H180.9500
Mn1—N52.285 (2)C9—H90.9500
Cl5—C511.759 (3)C44—H440.9500
Cl7—C511.769 (4)C012—C321.504 (3)
Cl6—C511.758 (3)C32—C371.386 (4)
Cl3—C501.756 (4)C32—C331.391 (4)
Cl2—C501.755 (4)C39—C401.393 (4)
Cl4—C501.740 (4)C39—H390.9500
N2—C61.382 (3)C14—C131.347 (4)
N2—C31.383 (3)C14—H140.9500
N4—C121.378 (3)C33—C341.380 (4)
N4—C151.386 (3)C33—H330.9500
N3—C111.376 (3)C13—H130.9500
N3—C81.383 (3)C48—C491.354 (4)
N7—C471.312 (3)C48—H480.9500
N7—C481.380 (3)C27—C281.391 (4)
N1—C11.378 (3)C27—H270.9500
N1—C171.381 (3)C31—C301.396 (4)
N5—C441.315 (3)C31—H310.9500
N5—C461.373 (4)C43—C421.386 (4)
N6—C441.343 (3)C43—H430.9500
N6—C451.354 (4)C25—C241.395 (4)
N6—H60.8800C25—H250.9500
N8—C471.336 (3)C29—C301.378 (4)
N8—C491.358 (4)C29—C281.382 (4)
N8—H80.8800C29—H290.9500
C26—C271.388 (4)C30—H300.9500
C26—C311.393 (4)C42—C411.378 (4)
C26—C71.500 (3)C42—H420.9500
C6—C71.393 (3)C35—C361.379 (4)
C6—C51.432 (3)C35—C341.387 (4)
C15—C161.390 (4)C35—H350.9500
C15—C141.435 (3)C37—C361.396 (4)
C3—C21.396 (3)C37—H370.9500
C3—C41.432 (3)C19—H190.9500
C16—C171.394 (4)C46—C451.354 (4)
C16—C381.499 (3)C46—H460.9500
C17—C181.434 (4)C41—C401.381 (4)
C1—C21.395 (4)C41—H410.9500
C1—C191.439 (3)C34—H340.9500
C7—C81.390 (3)C28—H280.9500
C8—C91.437 (4)C21—C221.390 (4)
C12—C0121.394 (4)C21—H210.9500
C12—C131.432 (3)C40—H400.9500
C4—C51.353 (4)C45—H450.9500
C4—H40.9500C36—H360.9500
C2—C201.500 (3)C24—C231.379 (5)
C5—H50.9500C24—H240.9500
C47—H470.9500C49—H490.9500
C20—C251.388 (4)C23—C221.371 (5)
C20—C211.390 (4)C23—H230.9500
C38—C391.393 (4)C22—H220.9500
C38—C431.395 (4)C50—H501.0000
C10—C91.350 (4)C51—H511.0000
N2—Mn1—N189.59 (8)N6—C44—H44124.3
N2—Mn1—N390.21 (8)C11—C012—C12124.7 (2)
N1—Mn1—N3179.75 (9)C11—C012—C32117.9 (2)
N2—Mn1—N4178.75 (8)C12—C012—C32117.2 (2)
N1—Mn1—N490.10 (8)C37—C32—C33119.0 (2)
N3—Mn1—N490.11 (8)C37—C32—C012121.8 (2)
N2—Mn1—N791.37 (8)C33—C32—C012119.3 (2)
N1—Mn1—N792.09 (8)C38—C39—C40120.0 (3)
N3—Mn1—N788.05 (8)C38—C39—H39120.0
N4—Mn1—N787.43 (8)C40—C39—H39120.0
N2—Mn1—N588.13 (8)C13—C14—C15107.5 (2)
N1—Mn1—N589.17 (8)C13—C14—H14126.2
N3—Mn1—N590.69 (8)C15—C14—H14126.2
N4—Mn1—N593.08 (8)C34—C33—C32120.8 (3)
N7—Mn1—N5178.65 (7)C34—C33—H33119.6
C6—N2—C3106.27 (19)C32—C33—H33119.6
C6—N2—Mn1126.44 (16)C14—C13—C12107.7 (2)
C3—N2—Mn1127.08 (16)C14—C13—H13126.2
C12—N4—C15106.4 (2)C12—C13—H13126.2
C12—N4—Mn1126.27 (16)C49—C48—N7109.6 (2)
C15—N4—Mn1126.29 (16)C49—C48—H48125.2
C11—N3—C8106.43 (19)N7—C48—H48125.2
C11—N3—Mn1126.75 (16)C26—C27—C28120.3 (2)
C8—N3—Mn1126.69 (16)C26—C27—H27119.8
C47—N7—C48104.9 (2)C28—C27—H27119.8
C47—N7—Mn1125.51 (17)C26—C31—C30120.0 (2)
C48—N7—Mn1128.14 (17)C26—C31—H31120.0
C1—N1—C17106.45 (19)C30—C31—H31120.0
C1—N1—Mn1127.05 (16)C42—C43—C38120.6 (3)
C17—N1—Mn1126.50 (16)C42—C43—H43119.7
C44—N5—C46105.1 (2)C38—C43—H43119.7
C44—N5—Mn1127.14 (18)C20—C25—C24120.2 (3)
C46—N5—Mn1127.67 (18)C20—C25—H25119.9
C44—N6—C45107.5 (2)C24—C25—H25119.9
C44—N6—H6126.3C30—C29—C28119.9 (2)
C45—N6—H6126.3C30—C29—H29120.0
C47—N8—C49107.4 (2)C28—C29—H29120.0
C47—N8—H8126.3C29—C30—C31120.3 (2)
C49—N8—H8126.3C29—C30—H30119.9
C27—C26—C31119.2 (2)C31—C30—H30119.9
C27—C26—C7119.5 (2)C41—C42—C43119.9 (3)
C31—C26—C7121.3 (2)C41—C42—H42120.0
N2—C6—C7126.3 (2)C43—C42—H42120.0
N2—C6—C5109.6 (2)C36—C35—C34119.8 (3)
C7—C6—C5124.0 (2)C36—C35—H35120.1
N4—C15—C16125.8 (2)C34—C35—H35120.1
N4—C15—C14109.0 (2)C32—C37—C36120.3 (3)
C16—C15—C14125.2 (2)C32—C37—H37119.8
N2—C3—C2125.9 (2)C36—C37—H37119.8
N2—C3—C4109.2 (2)C18—C19—C1107.3 (2)
C2—C3—C4124.9 (2)C18—C19—H19126.3
C15—C16—C17124.5 (2)C1—C19—H19126.3
C15—C16—C38117.7 (2)C45—C46—N5109.8 (3)
C17—C16—C38117.6 (2)C45—C46—H46125.1
N1—C17—C16126.1 (2)N5—C46—H46125.1
N1—C17—C18109.4 (2)C42—C41—C40120.3 (3)
C16—C17—C18124.5 (2)C42—C41—H41119.9
N1—C1—C2126.1 (2)C40—C41—H41119.9
N1—C1—C19109.3 (2)C33—C34—C35120.1 (3)
C2—C1—C19124.5 (2)C33—C34—H34120.0
C8—C7—C6124.4 (2)C35—C34—H34120.0
C8—C7—C26118.7 (2)C29—C28—C27120.3 (3)
C6—C7—C26116.9 (2)C29—C28—H28119.9
N3—C8—C7125.8 (2)C27—C28—H28119.9
N3—C8—C9109.4 (2)C20—C21—C22120.2 (3)
C7—C8—C9124.8 (2)C20—C21—H21119.9
N4—C12—C012126.1 (2)C22—C21—H21119.9
N4—C12—C13109.3 (2)C41—C40—C39120.1 (3)
C012—C12—C13124.4 (2)C41—C40—H40119.9
C5—C4—C3107.8 (2)C39—C40—H40119.9
C5—C4—H4126.1C46—C45—N6106.2 (2)
C3—C4—H4126.1C46—C45—H45126.9
C1—C2—C3123.8 (2)N6—C45—H45126.9
C1—C2—C20117.9 (2)C35—C36—C37120.1 (3)
C3—C2—C20118.3 (2)C35—C36—H36120.0
C4—C5—C6107.1 (2)C37—C36—H36120.0
C4—C5—H5126.4C23—C24—C25119.8 (3)
C6—C5—H5126.4C23—C24—H24120.1
N7—C47—N8111.9 (2)C25—C24—H24120.1
N7—C47—H47124.0C48—C49—N8106.2 (2)
N8—C47—H47124.0C48—C49—H49126.9
C25—C20—C21119.2 (3)N8—C49—H49126.9
C25—C20—C2120.9 (2)C22—C23—C24120.4 (3)
C21—C20—C2119.9 (3)C22—C23—H23119.8
C39—C38—C43119.0 (2)C24—C23—H23119.8
C39—C38—C16122.0 (2)C23—C22—C21120.2 (3)
C43—C38—C16119.0 (2)C23—C22—H22119.9
C9—C10—C11107.5 (2)C21—C22—H22119.9
C9—C10—H10126.3Cl4—C50—Cl2112.8 (2)
C11—C10—H10126.3Cl4—C50—Cl3110.1 (2)
N3—C11—C012125.9 (2)Cl2—C50—Cl3108.20 (18)
N3—C11—C10109.4 (2)Cl4—C50—H50108.5
C012—C11—C10124.6 (2)Cl2—C50—H50108.5
C19—C18—C17107.5 (2)Cl3—C50—H50108.5
C19—C18—H18126.3Cl6—C51—Cl5109.7 (2)
C17—C18—H18126.3Cl6—C51—Cl7112.12 (18)
C10—C9—C8107.3 (2)Cl5—C51—Cl7109.62 (17)
C10—C9—H9126.4Cl6—C51—H51108.4
C8—C9—H9126.4Cl5—C51—H51108.4
N5—C44—N6111.5 (2)Cl7—C51—H51108.4
N5—C44—H44124.3
Bis(piperidine)(5,10,15,20-tetraphenylporphyrinato)manganese(III) dichloride (II_Piperidine) top
Crystal data top
[Mn(C44H28N4)(C5H11N)2]ClZ = 1
Mr = 873.39F(000) = 475
Triclinic, P1Dx = 1.068 Mg m3
a = 10.5211 (1) ÅCu Kα radiation, λ = 1.54178 Å
b = 11.9123 (1) ÅCell parameters from 9895 reflections
c = 12.6355 (1) Åθ = 3.9–68.8°
α = 66.1342 (5)°µ = 3.04 mm1
β = 78.3107 (5)°T = 100 K
γ = 89.5778 (6)°Plate, green
V = 1413.24 (2) Å30.48 × 0.26 × 0.24 mm
Data collection top
Bruker SMART CCD APEXII area-detector
diffractometer
4750 independent reflections
Radiation source: fine-focus sealed tube4719 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 69.2°, θmin = 3.9°
Absorption correction: numerical
(SADABS; Krause et al., 2015)
h = 1212
Tmin = 0.406, Tmax = 0.572k = 1414
13568 measured reflectionsl = 1415
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0548P)2 + 1.6375P]
where P = (Fo2 + 2Fc2)/3
4750 reflections(Δ/σ)max < 0.001
286 parametersΔρmax = 0.70 e Å3
0 restraintsΔρmin = 1.00 e Å3
Special details top

Experimental. Crystal mounted on a Cryoloop using Paratone-N.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Mn10.00000.00000.00000.01474 (13)
N10.01241 (17)0.12201 (16)0.16365 (15)0.0169 (4)
N20.08899 (17)0.13330 (16)0.02570 (15)0.0171 (4)
C50.1288 (2)0.0124 (2)0.22581 (18)0.0179 (4)
N30.20868 (17)0.04247 (16)0.08114 (16)0.0193 (4)
H40.25230.03810.14330.023*
C40.0683 (2)0.09966 (19)0.24354 (18)0.0180 (4)
C90.1172 (2)0.25531 (19)0.05315 (18)0.0180 (4)
C10.0261 (2)0.24636 (19)0.21445 (18)0.0187 (4)
C20.0052 (2)0.3012 (2)0.32931 (19)0.0227 (5)
H20.01100.38560.38260.027*
C70.2035 (2)0.2348 (2)0.10181 (19)0.0198 (4)
H60.24800.25000.15370.024*
C30.0613 (2)0.2119 (2)0.34786 (19)0.0221 (5)
H30.09070.22110.41700.026*
C60.1391 (2)0.1199 (2)0.12281 (18)0.0178 (4)
C80.1894 (2)0.3177 (2)0.00536 (19)0.0208 (5)
H70.22160.40200.04230.025*
C110.1889 (2)0.01770 (19)0.32161 (18)0.0203 (5)
C120.3024 (2)0.0395 (2)0.3443 (2)0.0272 (5)
H120.34090.08440.30050.033*
C160.1336 (2)0.0817 (2)0.3880 (2)0.0245 (5)
H160.05570.12020.37380.029*
C130.3593 (2)0.0306 (3)0.4315 (2)0.0370 (7)
H130.43660.06980.44690.044*
C140.3044 (3)0.0345 (3)0.4954 (2)0.0378 (7)
H140.34460.04120.55370.045*
C150.1909 (3)0.0900 (2)0.4747 (2)0.0322 (6)
H150.15210.13380.51960.039*
C100.0841 (2)0.31042 (19)0.16334 (18)0.0183 (4)
C270.2056 (2)0.1249 (2)0.1419 (2)0.0278 (5)
H26A0.16040.20540.08390.033*
H26B0.15470.08920.20400.033*
C230.2936 (2)0.0884 (2)0.0057 (2)0.0271 (5)
H22A0.30050.02820.04030.033*
H22B0.25190.16680.07090.033*
C250.4250 (2)0.1950 (3)0.1089 (3)0.0349 (6)
H24A0.38880.27830.04960.042*
H24B0.51420.20150.14890.042*
C260.3409 (2)0.1459 (3)0.1992 (2)0.0339 (6)
H25A0.38310.06730.26370.041*
H25B0.33260.20540.23440.041*
C240.4303 (2)0.1098 (3)0.0472 (2)0.0319 (6)
H23A0.47890.14640.01660.038*
H23B0.47720.02990.10490.038*
C180.0443 (2)0.5239 (2)0.1815 (2)0.0227 (5)
H180.01760.48910.10820.027*
C170.1110 (2)0.44701 (19)0.22903 (18)0.0190 (4)
C220.2013 (2)0.4992 (2)0.33633 (19)0.0213 (5)
H220.24720.44770.36920.026*
C200.1581 (2)0.7025 (2)0.3484 (2)0.0244 (5)
H200.17380.78940.38930.029*
C210.2248 (2)0.6266 (2)0.3957 (2)0.0235 (5)
H210.28680.66170.46890.028*
C190.0682 (2)0.6506 (2)0.2410 (2)0.0252 (5)
H190.02280.70230.20820.030*
Cl10.62779 (10)0.79940 (7)0.31554 (8)0.0748 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0192 (2)0.0113 (2)0.0121 (2)0.00178 (18)0.00382 (18)0.00305 (18)
N10.0204 (9)0.0136 (8)0.0151 (8)0.0016 (7)0.0042 (7)0.0041 (7)
N20.0207 (9)0.0146 (9)0.0131 (8)0.0029 (7)0.0026 (7)0.0034 (7)
C50.0173 (10)0.0193 (11)0.0160 (10)0.0036 (8)0.0027 (8)0.0068 (8)
N30.0199 (9)0.0178 (9)0.0194 (9)0.0027 (7)0.0031 (7)0.0076 (7)
C40.0185 (10)0.0189 (11)0.0150 (10)0.0037 (8)0.0033 (8)0.0055 (8)
C90.0194 (10)0.0152 (10)0.0165 (10)0.0023 (8)0.0005 (8)0.0053 (8)
C10.0204 (10)0.0154 (10)0.0172 (10)0.0029 (8)0.0030 (8)0.0043 (8)
C20.0284 (12)0.0160 (11)0.0179 (10)0.0026 (9)0.0068 (9)0.0004 (9)
C70.0206 (10)0.0207 (11)0.0191 (10)0.0000 (9)0.0049 (9)0.0088 (9)
C30.0267 (11)0.0220 (11)0.0159 (10)0.0037 (9)0.0082 (9)0.0045 (9)
C60.0168 (10)0.0200 (11)0.0169 (10)0.0049 (8)0.0034 (8)0.0080 (9)
C80.0233 (11)0.0169 (11)0.0196 (10)0.0020 (9)0.0014 (9)0.0065 (9)
C110.0210 (10)0.0170 (10)0.0172 (10)0.0039 (9)0.0052 (9)0.0007 (8)
C120.0190 (11)0.0294 (13)0.0229 (11)0.0002 (10)0.0020 (9)0.0015 (10)
C160.0292 (12)0.0211 (11)0.0230 (11)0.0004 (10)0.0091 (10)0.0073 (9)
C130.0192 (11)0.0420 (15)0.0325 (13)0.0072 (11)0.0119 (10)0.0052 (12)
C140.0389 (15)0.0416 (15)0.0270 (13)0.0165 (12)0.0143 (12)0.0046 (11)
C150.0441 (15)0.0278 (13)0.0251 (12)0.0076 (11)0.0109 (11)0.0095 (10)
C100.0191 (10)0.0156 (10)0.0171 (10)0.0019 (8)0.0004 (8)0.0054 (8)
C270.0232 (11)0.0355 (13)0.0359 (13)0.0074 (10)0.0090 (10)0.0248 (11)
C230.0231 (11)0.0364 (14)0.0264 (12)0.0059 (10)0.0082 (10)0.0165 (11)
C250.0250 (12)0.0409 (15)0.0493 (16)0.0134 (11)0.0104 (12)0.0282 (13)
C260.0253 (12)0.0513 (16)0.0426 (15)0.0114 (11)0.0090 (11)0.0363 (13)
C240.0244 (12)0.0419 (15)0.0365 (14)0.0079 (11)0.0098 (11)0.0218 (12)
C180.0254 (11)0.0192 (11)0.0203 (11)0.0028 (9)0.0024 (9)0.0060 (9)
C170.0230 (11)0.0166 (11)0.0163 (10)0.0025 (9)0.0069 (9)0.0044 (9)
C220.0251 (11)0.0184 (11)0.0191 (10)0.0032 (9)0.0054 (9)0.0060 (9)
C200.0284 (12)0.0137 (10)0.0274 (12)0.0007 (9)0.0092 (10)0.0033 (9)
C210.0245 (11)0.0201 (11)0.0194 (11)0.0006 (9)0.0043 (9)0.0018 (9)
C190.0301 (12)0.0193 (11)0.0282 (12)0.0050 (10)0.0067 (10)0.0116 (10)
Cl10.0919 (7)0.0278 (4)0.0688 (6)0.0020 (4)0.0379 (5)0.0096 (4)
Geometric parameters (Å, º) top
Mn1—N2i2.0164 (17)C7—C81.352 (3)
Mn1—N22.0164 (17)C7—C61.432 (3)
Mn1—N12.0199 (17)C11—C161.391 (3)
Mn1—N1i2.0199 (17)C11—C121.393 (3)
Mn1—N3i2.3704 (17)C12—C131.395 (4)
Mn1—N32.3704 (17)C16—C151.389 (3)
N1—C41.377 (3)C13—C141.379 (4)
N1—C11.380 (3)C14—C151.380 (4)
N2—C91.381 (3)C10—C1i1.392 (3)
N2—C61.383 (3)C10—C171.495 (3)
C5—C61.393 (3)C27—C261.528 (3)
C5—C41.397 (3)C23—C241.523 (3)
C5—C111.497 (3)C25—C261.513 (4)
N3—C271.475 (3)C25—C241.516 (3)
N3—C231.485 (3)C18—C191.384 (3)
C4—C31.437 (3)C18—C171.400 (3)
C9—C101.395 (3)C17—C221.390 (3)
C9—C81.432 (3)C22—C211.391 (3)
C1—C10i1.392 (3)C20—C211.387 (3)
C1—C21.437 (3)C20—C191.388 (3)
C2—C31.343 (3)
N2i—Mn1—N2180.00 (11)N1—C1—C2109.10 (18)
N2i—Mn1—N190.22 (7)C10i—C1—C2124.7 (2)
N2—Mn1—N189.78 (7)C3—C2—C1107.84 (19)
N2i—Mn1—N1i89.78 (7)C8—C7—C6107.44 (19)
N2—Mn1—N1i90.22 (7)C2—C3—C4107.14 (19)
N1—Mn1—N1i180.00 (16)N2—C6—C5125.96 (19)
N2i—Mn1—N3i91.99 (6)N2—C6—C7109.31 (18)
N2—Mn1—N3i88.01 (6)C5—C6—C7124.72 (19)
N1—Mn1—N3i90.59 (7)C7—C8—C9107.55 (19)
N1i—Mn1—N3i89.41 (7)C16—C11—C12118.9 (2)
N2i—Mn1—N388.01 (6)C16—C11—C5120.6 (2)
N2—Mn1—N391.99 (6)C12—C11—C5120.5 (2)
N1—Mn1—N389.41 (7)C11—C12—C13119.8 (2)
N1i—Mn1—N390.59 (7)C15—C16—C11120.9 (2)
N3i—Mn1—N3180.00 (11)C14—C13—C12120.6 (2)
C4—N1—C1106.32 (17)C13—C14—C15120.0 (2)
C4—N1—Mn1126.99 (14)C14—C15—C16119.8 (2)
C1—N1—Mn1126.58 (14)C1i—C10—C9124.0 (2)
C9—N2—C6106.39 (17)C1i—C10—C17118.44 (19)
C9—N2—Mn1126.52 (14)C9—C10—C17117.53 (19)
C6—N2—Mn1127.03 (14)N3—C27—C26113.36 (19)
C6—C5—C4123.91 (19)N3—C23—C24113.92 (19)
C6—C5—C11117.60 (18)C26—C25—C24110.1 (2)
C4—C5—C11118.48 (18)C25—C26—C27111.0 (2)
C27—N3—C23110.07 (17)C25—C24—C23110.9 (2)
C27—N3—Mn1114.10 (13)C19—C18—C17120.1 (2)
C23—N3—Mn1113.57 (13)C22—C17—C18119.31 (19)
N1—C4—C5126.17 (19)C22—C17—C10121.30 (19)
N1—C4—C3109.57 (18)C18—C17—C10119.39 (19)
C5—C4—C3124.18 (19)C17—C22—C21120.2 (2)
N2—C9—C10126.23 (19)C21—C20—C19119.6 (2)
N2—C9—C8109.27 (18)C20—C21—C22120.3 (2)
C10—C9—C8124.49 (19)C18—C19—C20120.4 (2)
N1—C1—C10i126.20 (19)
Symmetry code: (i) x, y, z.
Chlorido(pyridine)(5,10,15,20-tetraphenylporphryinato)manganese(III) pyridine disolvate (III_Pyridine) top
Crystal data top
[Mn(C44H28N4)Cl(C5H5N)]·2C5H5NZ = 2
Mr = 940.39F(000) = 976
Triclinic, P1Dx = 1.345 Mg m3
a = 11.0499 (1) ÅCu Kα radiation, λ = 1.54178 Å
b = 12.1051 (1) ÅCell parameters from 9885 reflections
c = 18.5362 (2) Åθ = 2.4–68.6°
α = 90.177 (1)°µ = 3.22 mm1
β = 90.324 (1)°T = 100 K
γ = 110.537 (1)°Block, black
V = 2321.76 (4) Å30.30 × 0.26 × 0.24 mm
Data collection top
Bruker SMART CCD APEXII area-detector
diffractometer
7797 independent reflections
Radiation source: fine-focus sealed tube7543 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 68.7°, θmin = 2.4°
Absorption correction: numerical
(SADABS; Krause et al., 2015)
h = 1212
Tmin = 0.501, Tmax = 0.653k = 1414
21813 measured reflectionsl = 2120
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)] = 0.028H-atom parameters constrained
wR(F2) = 0.077 w = 1/[σ2(Fo2) + (0.038P)2 + 0.7188P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.002
7797 reflectionsΔρmax = 0.25 e Å3
614 parametersΔρmin = 0.31 e Å3
0 restraintsExtinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00110 (9)
Special details top

Experimental. Crystal mounted on a Cryoloop using Paratone-N.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Mn10.25000 (2)0.25259 (2)0.26425 (2)0.01129 (7)
Cl10.05275 (3)0.07601 (3)0.27497 (2)0.01823 (9)
N30.28699 (11)0.18844 (10)0.17020 (6)0.0131 (2)
N20.16611 (11)0.35000 (10)0.21006 (6)0.0138 (2)
N40.35308 (11)0.17105 (10)0.31700 (6)0.0129 (2)
N10.23015 (11)0.33306 (10)0.35623 (6)0.0136 (2)
N50.45322 (12)0.41540 (11)0.25495 (6)0.0170 (3)
N60.59232 (13)0.39758 (12)0.04010 (8)0.0276 (3)
C190.35666 (13)0.15735 (12)0.39042 (8)0.0135 (3)
C160.42241 (13)0.10803 (12)0.28697 (8)0.0134 (3)
C140.36984 (13)0.12807 (12)0.15901 (7)0.0136 (3)
C90.11901 (13)0.33012 (12)0.14042 (8)0.0148 (3)
C390.33748 (14)0.20485 (12)0.51979 (8)0.0154 (3)
C60.13100 (13)0.44033 (12)0.23724 (8)0.0151 (3)
C40.20063 (13)0.43432 (12)0.36279 (8)0.0148 (3)
C270.09681 (14)0.25070 (13)0.01496 (8)0.0152 (3)
C150.43798 (13)0.09316 (12)0.21294 (8)0.0136 (3)
C110.23185 (13)0.19582 (12)0.10456 (7)0.0139 (3)
C10.26374 (13)0.30786 (13)0.42388 (8)0.0146 (3)
C330.53214 (14)0.03633 (13)0.19083 (7)0.0150 (3)
C70.05806 (14)0.47601 (13)0.18378 (8)0.0178 (3)
H70.02280.53670.18880.021*
C170.46955 (14)0.05208 (13)0.34355 (8)0.0165 (3)
H170.52100.00420.33750.020*
C200.31388 (13)0.22013 (12)0.44175 (8)0.0145 (3)
C50.15543 (13)0.48713 (12)0.30716 (8)0.0152 (3)
C350.75424 (15)0.04324 (15)0.18735 (8)0.0233 (3)
H350.84270.08170.19980.028*
C280.00599 (15)0.14826 (13)0.01309 (8)0.0191 (3)
H280.03160.08250.01750.023*
N70.26832 (14)0.70063 (14)0.56772 (9)0.0359 (4)
C120.28312 (14)0.13959 (13)0.05048 (8)0.0161 (3)
H120.26010.13130.00080.019*
C80.04876 (14)0.40704 (13)0.12464 (8)0.0173 (3)
H80.00420.40930.08100.021*
C490.47837 (15)0.49069 (14)0.19981 (8)0.0207 (3)
H490.41530.47750.16260.025*
C400.23800 (15)0.14101 (13)0.56488 (8)0.0201 (3)
H400.15300.10580.54580.024*
C210.12741 (14)0.59728 (12)0.32143 (8)0.0157 (3)
C180.42704 (14)0.08038 (13)0.40676 (8)0.0163 (3)
H180.44100.05430.45330.020*
C30.21752 (14)0.47356 (13)0.43655 (8)0.0177 (3)
H30.20550.54200.45530.021*
C340.66264 (14)0.09132 (14)0.20836 (8)0.0196 (3)
H340.68940.16300.23520.024*
C130.37026 (14)0.10065 (13)0.08331 (8)0.0159 (3)
H130.42190.06240.06070.019*
C380.49484 (14)0.06955 (13)0.15206 (8)0.0176 (3)
H380.40630.10930.14050.021*
C20.25384 (14)0.39468 (13)0.47430 (8)0.0179 (3)
H20.26980.39640.52480.021*
C100.14712 (13)0.25626 (12)0.09031 (8)0.0143 (3)
C220.19665 (15)0.70084 (13)0.28517 (8)0.0189 (3)
H220.26370.70150.25310.023*
C320.14656 (14)0.34803 (13)0.03030 (8)0.0194 (3)
H320.20690.41950.01170.023*
C260.03019 (14)0.59893 (13)0.36883 (8)0.0197 (3)
H260.01700.52980.39470.024*
C230.16871 (16)0.80310 (13)0.29541 (9)0.0224 (3)
H230.21740.87330.27090.027*
C410.26093 (16)0.12787 (14)0.63777 (8)0.0231 (3)
H410.19230.08300.66800.028*
C310.10873 (15)0.34110 (14)0.10188 (8)0.0216 (3)
H310.14270.40800.13210.026*
C290.03044 (15)0.14082 (14)0.08518 (9)0.0229 (3)
H290.09110.06960.10390.027*
C420.38407 (16)0.18045 (14)0.66576 (8)0.0214 (3)
H420.40050.17140.71540.026*
C360.71595 (16)0.06108 (15)0.14808 (8)0.0232 (3)
H360.77820.09410.13340.028*
C370.58662 (16)0.11725 (14)0.13029 (8)0.0212 (3)
H370.56060.18860.10310.025*
C300.02151 (15)0.23702 (15)0.12989 (8)0.0222 (3)
H300.00240.23180.17940.027*
C250.00217 (15)0.70140 (14)0.37823 (9)0.0244 (3)
H250.06440.70160.41040.029*
C440.46069 (15)0.25817 (15)0.54889 (8)0.0235 (3)
H440.52960.30300.51880.028*
C240.07045 (16)0.80309 (14)0.34114 (9)0.0244 (4)
H240.04980.87240.34710.029*
C460.65926 (16)0.53058 (14)0.30564 (9)0.0250 (4)
H460.72060.54220.34360.030*
C560.12331 (16)0.75725 (15)0.64284 (9)0.0274 (4)
H560.07990.74960.68760.033*
C450.54398 (15)0.43615 (14)0.30688 (8)0.0219 (3)
H450.52810.38330.34640.026*
C470.68391 (16)0.60767 (14)0.24838 (9)0.0265 (4)
H470.76230.67350.24620.032*
C430.48364 (16)0.24635 (16)0.62149 (9)0.0271 (4)
H430.56800.28360.64100.032*
C570.10590 (16)0.83005 (15)0.58995 (9)0.0290 (4)
H570.04990.87330.59720.035*
C480.59169 (16)0.58689 (14)0.19408 (9)0.0267 (4)
H480.60600.63780.15360.032*
C540.68179 (17)0.35615 (16)0.06430 (10)0.0321 (4)
H540.69990.36170.11450.039*
C580.17241 (18)0.83840 (16)0.52590 (10)0.0335 (4)
H580.16440.88890.48850.040*
C500.57007 (16)0.38918 (14)0.03096 (9)0.0270 (4)
H500.50700.41830.04960.032*
C510.63330 (17)0.34079 (16)0.07861 (10)0.0318 (4)
H510.61490.33770.12870.038*
C550.20516 (16)0.69548 (15)0.62960 (10)0.0307 (4)
H550.21720.64640.66680.037*
C590.25042 (18)0.77214 (17)0.51750 (10)0.0361 (4)
H590.29440.77780.47300.043*
C530.74970 (17)0.30561 (17)0.02065 (12)0.0381 (5)
H530.81270.27750.04040.046*
C520.72378 (17)0.29689 (16)0.05232 (11)0.0377 (5)
H520.76750.26130.08380.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.01350 (12)0.01365 (13)0.00933 (13)0.00804 (9)0.00088 (8)0.00011 (8)
Cl10.01423 (17)0.01765 (18)0.0226 (2)0.00532 (13)0.00011 (13)0.00237 (13)
N30.0144 (6)0.0150 (6)0.0113 (6)0.0068 (5)0.0005 (5)0.0013 (4)
N20.0158 (6)0.0147 (6)0.0124 (6)0.0073 (5)0.0010 (5)0.0002 (4)
N40.0147 (6)0.0144 (6)0.0109 (6)0.0067 (5)0.0006 (5)0.0002 (4)
N10.0162 (6)0.0149 (6)0.0119 (6)0.0080 (5)0.0000 (5)0.0011 (4)
N50.0182 (6)0.0178 (6)0.0159 (7)0.0076 (5)0.0010 (5)0.0000 (5)
N60.0254 (7)0.0258 (7)0.0295 (8)0.0063 (6)0.0029 (6)0.0037 (6)
C190.0144 (7)0.0150 (7)0.0119 (7)0.0061 (6)0.0008 (5)0.0021 (5)
C160.0123 (6)0.0128 (7)0.0159 (7)0.0053 (5)0.0010 (5)0.0007 (5)
C140.0128 (7)0.0140 (7)0.0140 (7)0.0045 (5)0.0006 (5)0.0006 (5)
C90.0144 (7)0.0160 (7)0.0140 (8)0.0051 (6)0.0007 (5)0.0022 (5)
C390.0227 (7)0.0163 (7)0.0123 (7)0.0132 (6)0.0002 (6)0.0004 (5)
C60.0142 (7)0.0135 (7)0.0186 (8)0.0061 (6)0.0007 (6)0.0015 (5)
C40.0147 (7)0.0147 (7)0.0169 (8)0.0073 (6)0.0004 (5)0.0009 (5)
C270.0167 (7)0.0190 (7)0.0133 (7)0.0106 (6)0.0018 (6)0.0005 (5)
C150.0120 (7)0.0131 (7)0.0154 (7)0.0039 (5)0.0005 (5)0.0009 (5)
C110.0145 (7)0.0149 (7)0.0111 (7)0.0038 (6)0.0010 (5)0.0005 (5)
C10.0150 (7)0.0174 (7)0.0121 (7)0.0066 (6)0.0012 (5)0.0016 (5)
C330.0180 (7)0.0192 (7)0.0108 (7)0.0105 (6)0.0001 (5)0.0011 (5)
C70.0188 (7)0.0177 (7)0.0209 (8)0.0112 (6)0.0023 (6)0.0007 (6)
C170.0190 (7)0.0168 (7)0.0171 (8)0.0106 (6)0.0028 (6)0.0008 (6)
C200.0146 (7)0.0164 (7)0.0127 (7)0.0058 (6)0.0003 (5)0.0012 (5)
C50.0148 (7)0.0149 (7)0.0171 (8)0.0067 (6)0.0002 (5)0.0009 (5)
C350.0177 (7)0.0361 (9)0.0193 (8)0.0136 (7)0.0017 (6)0.0018 (6)
C280.0216 (7)0.0185 (8)0.0177 (8)0.0077 (6)0.0017 (6)0.0014 (6)
N70.0282 (8)0.0327 (9)0.0457 (10)0.0095 (7)0.0001 (7)0.0166 (7)
C120.0183 (7)0.0199 (8)0.0103 (7)0.0071 (6)0.0010 (6)0.0008 (5)
C80.0184 (7)0.0199 (8)0.0156 (8)0.0094 (6)0.0044 (6)0.0016 (6)
C490.0214 (8)0.0234 (8)0.0202 (8)0.0116 (6)0.0006 (6)0.0024 (6)
C400.0221 (8)0.0205 (8)0.0175 (8)0.0073 (6)0.0003 (6)0.0013 (6)
C210.0174 (7)0.0153 (7)0.0166 (8)0.0085 (6)0.0061 (6)0.0020 (5)
C180.0212 (7)0.0162 (7)0.0137 (7)0.0094 (6)0.0029 (6)0.0019 (5)
C30.0221 (7)0.0177 (8)0.0162 (8)0.0109 (6)0.0001 (6)0.0024 (6)
C340.0193 (8)0.0239 (8)0.0171 (8)0.0094 (6)0.0026 (6)0.0022 (6)
C130.0162 (7)0.0183 (7)0.0144 (7)0.0074 (6)0.0012 (6)0.0015 (5)
C380.0199 (7)0.0201 (8)0.0147 (8)0.0096 (6)0.0011 (6)0.0012 (6)
C20.0232 (8)0.0224 (8)0.0111 (7)0.0120 (6)0.0006 (6)0.0016 (6)
C100.0152 (7)0.0152 (7)0.0115 (7)0.0040 (6)0.0013 (5)0.0024 (5)
C220.0209 (7)0.0199 (8)0.0160 (8)0.0074 (6)0.0056 (6)0.0006 (6)
C320.0193 (7)0.0192 (8)0.0181 (8)0.0049 (6)0.0026 (6)0.0007 (6)
C260.0191 (7)0.0159 (7)0.0248 (8)0.0071 (6)0.0015 (6)0.0024 (6)
C230.0293 (8)0.0144 (7)0.0218 (8)0.0056 (6)0.0114 (6)0.0000 (6)
C410.0317 (9)0.0236 (8)0.0152 (8)0.0110 (7)0.0058 (6)0.0042 (6)
C310.0228 (8)0.0267 (8)0.0169 (8)0.0105 (7)0.0003 (6)0.0072 (6)
C290.0207 (8)0.0236 (8)0.0237 (9)0.0071 (6)0.0066 (6)0.0069 (6)
C420.0356 (9)0.0261 (8)0.0108 (7)0.0212 (7)0.0008 (6)0.0005 (6)
C360.0276 (8)0.0353 (9)0.0159 (8)0.0224 (7)0.0029 (6)0.0023 (6)
C370.0300 (8)0.0243 (8)0.0152 (8)0.0169 (7)0.0001 (6)0.0026 (6)
C300.0212 (8)0.0346 (9)0.0140 (8)0.0139 (7)0.0052 (6)0.0017 (6)
C250.0225 (8)0.0241 (8)0.0309 (9)0.0135 (7)0.0027 (7)0.0069 (7)
C440.0191 (8)0.0355 (9)0.0162 (8)0.0098 (7)0.0013 (6)0.0045 (6)
C240.0316 (9)0.0178 (8)0.0287 (9)0.0151 (7)0.0126 (7)0.0072 (6)
C460.0228 (8)0.0278 (9)0.0219 (9)0.0057 (7)0.0018 (6)0.0068 (6)
C560.0224 (8)0.0258 (9)0.0293 (9)0.0025 (7)0.0018 (7)0.0078 (7)
C450.0221 (8)0.0246 (8)0.0182 (8)0.0075 (7)0.0013 (6)0.0004 (6)
C470.0228 (8)0.0195 (8)0.0336 (10)0.0029 (7)0.0066 (7)0.0058 (7)
C430.0241 (8)0.0419 (10)0.0180 (9)0.0153 (7)0.0051 (6)0.0001 (7)
C570.0255 (9)0.0294 (9)0.0326 (10)0.0104 (7)0.0003 (7)0.0084 (7)
C480.0291 (9)0.0221 (8)0.0295 (9)0.0095 (7)0.0077 (7)0.0082 (7)
C540.0284 (9)0.0296 (9)0.0325 (10)0.0029 (8)0.0013 (7)0.0083 (7)
C580.0366 (10)0.0327 (10)0.0294 (10)0.0100 (8)0.0009 (8)0.0079 (7)
C500.0242 (8)0.0231 (9)0.0314 (10)0.0052 (7)0.0022 (7)0.0001 (7)
C510.0263 (9)0.0292 (9)0.0328 (10)0.0006 (7)0.0005 (7)0.0082 (7)
C550.0268 (9)0.0237 (9)0.0390 (11)0.0057 (7)0.0038 (7)0.0076 (7)
C590.0319 (10)0.0374 (11)0.0345 (11)0.0067 (8)0.0061 (8)0.0153 (8)
C530.0236 (9)0.0314 (10)0.0591 (13)0.0096 (8)0.0042 (8)0.0043 (9)
C520.0246 (9)0.0309 (10)0.0544 (13)0.0057 (8)0.0043 (8)0.0134 (9)
Geometric parameters (Å, º) top
Mn1—N42.0024 (12)C21—C221.395 (2)
Mn1—N22.0056 (12)C21—C261.397 (2)
Mn1—N32.0081 (12)C18—H180.9500
Mn1—N12.0119 (12)C3—C21.354 (2)
Mn1—N52.4203 (12)C3—H30.9500
Mn1—Cl12.4693 (4)C34—H340.9500
N3—C141.3732 (18)C13—H130.9500
N3—C111.3747 (19)C38—C371.392 (2)
N2—C61.3771 (18)C38—H380.9500
N2—C91.3776 (19)C2—H20.9500
N4—C191.3735 (18)C22—C231.390 (2)
N4—C161.3752 (18)C22—H220.9500
N1—C11.3709 (19)C32—C311.382 (2)
N1—C41.3798 (18)C32—H320.9500
N5—C491.336 (2)C26—C251.390 (2)
N5—C451.344 (2)C26—H260.9500
N6—C541.335 (2)C23—C241.381 (2)
N6—C501.339 (2)C23—H230.9500
C19—C201.400 (2)C41—C421.381 (2)
C19—C181.439 (2)C41—H410.9500
C16—C151.403 (2)C31—C301.387 (2)
C16—C171.441 (2)C31—H310.9500
C14—C151.401 (2)C29—C301.384 (2)
C14—C131.4413 (19)C29—H290.9500
C9—C101.397 (2)C42—C431.385 (2)
C9—C81.436 (2)C42—H420.9500
C39—C401.387 (2)C36—C371.387 (2)
C39—C441.391 (2)C36—H360.9500
C39—C201.492 (2)C37—H370.9500
C6—C51.399 (2)C30—H300.9500
C6—C71.434 (2)C25—C241.384 (2)
C4—C51.394 (2)C25—H250.9500
C4—C31.436 (2)C44—C431.385 (2)
C27—C281.390 (2)C44—H440.9500
C27—C321.397 (2)C24—H240.9500
C27—C101.493 (2)C46—C471.379 (2)
C15—C331.493 (2)C46—C451.382 (2)
C11—C101.400 (2)C46—H460.9500
C11—C121.4360 (19)C56—C571.377 (3)
C1—C201.399 (2)C56—C551.383 (2)
C1—C21.437 (2)C56—H560.9500
C33—C341.396 (2)C45—H450.9500
C33—C381.396 (2)C47—C481.386 (2)
C7—C81.357 (2)C47—H470.9500
C7—H70.9500C43—H430.9500
C17—C181.352 (2)C57—C581.385 (2)
C17—H170.9500C57—H570.9500
C5—C211.494 (2)C48—H480.9500
C35—C361.385 (2)C54—C531.382 (3)
C35—C341.390 (2)C54—H540.9500
C35—H350.9500C58—C591.377 (3)
C28—C291.387 (2)C58—H580.9500
C28—H280.9500C50—C511.376 (3)
N7—C591.333 (3)C50—H500.9500
N7—C551.336 (2)C51—C521.377 (3)
C12—C131.354 (2)C51—H510.9500
C12—H120.9500C55—H550.9500
C8—H80.9500C59—H590.9500
C49—C481.384 (2)C53—C521.381 (3)
C49—H490.9500C53—H530.9500
C40—C411.393 (2)C52—H520.9500
C40—H400.9500
N4—Mn1—N2173.35 (5)C2—C3—H3126.4
N4—Mn1—N390.21 (5)C4—C3—H3126.4
N2—Mn1—N389.54 (5)C35—C34—C33121.25 (14)
N4—Mn1—N190.24 (5)C35—C34—H34119.4
N2—Mn1—N189.27 (5)C33—C34—H34119.4
N3—Mn1—N1173.61 (5)C12—C13—C14107.10 (13)
N4—Mn1—N585.07 (4)C12—C13—H13126.4
N2—Mn1—N588.27 (4)C14—C13—H13126.4
N3—Mn1—N589.41 (4)C37—C38—C33120.44 (14)
N1—Mn1—N584.28 (4)C37—C38—H38119.8
N4—Mn1—Cl190.71 (3)C33—C38—H38119.8
N2—Mn1—Cl195.93 (3)C3—C2—C1107.32 (13)
N3—Mn1—Cl188.82 (3)C3—C2—H2126.3
N1—Mn1—Cl197.55 (3)C1—C2—H2126.3
N5—Mn1—Cl1175.42 (3)C9—C10—C11123.38 (13)
C14—N3—C11107.03 (11)C9—C10—C27119.06 (13)
C14—N3—Mn1127.07 (9)C11—C10—C27117.21 (12)
C11—N3—Mn1125.89 (9)C23—C22—C21120.75 (15)
C6—N2—C9106.58 (11)C23—C22—H22119.6
C6—N2—Mn1126.97 (9)C21—C22—H22119.6
C9—N2—Mn1126.07 (9)C31—C32—C27120.51 (14)
C19—N4—C16106.88 (11)C31—C32—H32119.7
C19—N4—Mn1125.96 (9)C27—C32—H32119.7
C16—N4—Mn1126.85 (9)C25—C26—C21120.27 (15)
C1—N1—C4106.58 (11)C25—C26—H26119.9
C1—N1—Mn1125.58 (9)C21—C26—H26119.9
C4—N1—Mn1127.11 (9)C24—C23—C22120.25 (15)
C49—N5—C45117.15 (13)C24—C23—H23119.9
C49—N5—Mn1121.86 (10)C22—C23—H23119.9
C45—N5—Mn1120.95 (10)C42—C41—C40119.59 (15)
C54—N6—C50116.48 (15)C42—C41—H41120.2
N4—C19—C20125.37 (13)C40—C41—H41120.2
N4—C19—C18109.31 (12)C32—C31—C30120.41 (14)
C20—C19—C18124.83 (13)C32—C31—H31119.8
N4—C16—C15125.87 (13)C30—C31—H31119.8
N4—C16—C17109.21 (12)C30—C29—C28120.05 (14)
C15—C16—C17124.79 (13)C30—C29—H29120.0
N3—C14—C15125.52 (12)C28—C29—H29120.0
N3—C14—C13109.16 (12)C41—C42—C43119.98 (14)
C15—C14—C13125.25 (13)C41—C42—H42120.0
N2—C9—C10125.25 (13)C43—C42—H42120.0
N2—C9—C8109.46 (12)C35—C36—C37119.95 (14)
C10—C9—C8124.94 (14)C35—C36—H36120.0
C40—C39—C44118.83 (14)C37—C36—H36120.0
C40—C39—C20121.35 (13)C36—C37—C38120.28 (14)
C44—C39—C20119.79 (13)C36—C37—H37119.9
N2—C6—C5126.20 (13)C38—C37—H37119.9
N2—C6—C7109.42 (12)C29—C30—C31119.56 (14)
C5—C6—C7124.29 (13)C29—C30—H30120.2
N1—C4—C5125.30 (13)C31—C30—H30120.2
N1—C4—C3109.42 (12)C24—C25—C26120.57 (15)
C5—C4—C3125.22 (13)C24—C25—H25119.7
C28—C27—C32118.52 (14)C26—C25—H25119.7
C28—C27—C10121.58 (13)C43—C44—C39120.45 (15)
C32—C27—C10119.80 (13)C43—C44—H44119.8
C14—C15—C16123.67 (13)C39—C44—H44119.8
C14—C15—C33118.51 (12)C23—C24—C25119.59 (14)
C16—C15—C33117.83 (12)C23—C24—H24120.2
N3—C11—C10126.26 (13)C25—C24—H24120.2
N3—C11—C12109.18 (12)C47—C46—C45118.98 (15)
C10—C11—C12124.37 (13)C47—C46—H46120.5
N1—C1—C20126.55 (13)C45—C46—H46120.5
N1—C1—C2109.51 (12)C57—C56—C55118.85 (16)
C20—C1—C2123.60 (14)C57—C56—H56120.6
C34—C33—C38118.41 (13)C55—C56—H56120.6
C34—C33—C15119.22 (13)N5—C45—C46123.24 (15)
C38—C33—C15122.36 (13)N5—C45—H45118.4
C8—C7—C6107.38 (13)C46—C45—H45118.4
C8—C7—H7126.3C46—C47—C48118.46 (15)
C6—C7—H7126.3C46—C47—H47120.8
C18—C17—C16107.28 (13)C48—C47—H47120.8
C18—C17—H17126.4C42—C43—C44120.23 (15)
C16—C17—H17126.4C42—C43—H43119.9
C1—C20—C19123.38 (14)C44—C43—H43119.9
C1—C20—C39117.16 (12)C56—C57—C58118.07 (17)
C19—C20—C39118.99 (13)C56—C57—H57121.0
C4—C5—C6123.12 (13)C58—C57—H57121.0
C4—C5—C21119.95 (13)C49—C48—C47118.84 (15)
C6—C5—C21116.91 (12)C49—C48—H48120.6
C36—C35—C34119.66 (15)C47—C48—H48120.6
C36—C35—H35120.2N6—C54—C53123.86 (17)
C34—C35—H35120.2N6—C54—H54118.1
C29—C28—C27120.88 (14)C53—C54—H54118.1
C29—C28—H28119.6C59—C58—C57118.74 (19)
C27—C28—H28119.6C59—C58—H58120.6
C59—N7—C55116.02 (16)C57—C58—H58120.6
C13—C12—C11107.45 (13)N6—C50—C51123.76 (17)
C13—C12—H12126.3N6—C50—H50118.1
C11—C12—H12126.3C51—C50—H50118.1
C7—C8—C9107.11 (13)C50—C51—C52118.78 (17)
C7—C8—H8126.4C50—C51—H51120.6
C9—C8—H8126.4C52—C51—H51120.6
N5—C49—C48123.33 (15)N7—C55—C56123.99 (18)
N5—C49—H49118.3N7—C55—H55118.0
C48—C49—H49118.3C56—C55—H55118.0
C39—C40—C41120.90 (14)N7—C59—C58124.31 (17)
C39—C40—H40119.6N7—C59—H59117.8
C41—C40—H40119.6C58—C59—H59117.8
C22—C21—C26118.55 (13)C52—C53—C54118.43 (18)
C22—C21—C5119.75 (13)C52—C53—H53120.8
C26—C21—C5121.67 (13)C54—C53—H53120.8
C17—C18—C19107.27 (13)C51—C52—C53118.67 (17)
C17—C18—H18126.4C51—C52—H52120.7
C19—C18—H18126.4C53—C52—H52120.7
C2—C3—C4107.15 (13)
(1,4-Diazabicyclo[2.2.2]octane)(5,10,15,20-tetraphenylporphyrin)manganese(III) chloride–1,4-diazabicyclo[2.2.2]octane–toluene–water (4/4/4/1) (IV_DABCO) top
Crystal data top
[Mn(C44H28N4)(C6H12N2)]Cl·C6H12N2·C7H8·0.25H2OZ = 2
Mr = 1023.58F(000) = 1076
Triclinic, P1Dx = 1.310 Mg m3
a = 11.4402 (2) ÅCu Kα radiation, λ = 1.54178 Å
b = 13.4019 (3) ÅCell parameters from 9495 reflections
c = 18.6407 (4) Åθ = 2.4–68.6°
α = 95.774 (1)°µ = 2.95 mm1
β = 92.199 (1)°T = 100 K
γ = 113.630 (1)°Block, black
V = 2595.35 (9) Å30.24 × 0.22 × 0.18 mm
Data collection top
Bruker SMART CCD APEXII area-detector
diffractometer
8538 independent reflections
Radiation source: fine-focus sealed tube6596 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
φ and ω scansθmax = 66.7°, θmin = 2.4°
Absorption correction: numerical
(SADABS; Krause et al., 2015)
h = 1313
Tmin = 0.540, Tmax = 0.737k = 1515
24215 measured reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0887P)2 + 3.2657P]
where P = (Fo2 + 2Fc2)/3
8538 reflections(Δ/σ)max = 0.001
668 parametersΔρmax = 1.30 e Å3
12 restraintsΔρmin = 0.68 e Å3
Special details top

Experimental. Crystal mounted on a Cryoloop using Paratone-N.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Mn10.51095 (5)0.78380 (4)0.74011 (3)0.02184 (17)
Cl10.71084 (8)0.84537 (7)0.68325 (5)0.0299 (2)
N10.5974 (3)0.8617 (2)0.83868 (15)0.0241 (6)
N40.5218 (3)0.6448 (2)0.76577 (15)0.0246 (6)
N30.4063 (3)0.7013 (2)0.64754 (15)0.0227 (6)
N20.4790 (3)0.9171 (2)0.72023 (15)0.0230 (6)
N50.2951 (3)0.7187 (2)0.80052 (15)0.0241 (6)
N60.0798 (3)0.6573 (3)0.86100 (16)0.0321 (7)
N70.0925 (4)0.0075 (4)0.8352 (2)0.0681 (13)
N80.0735 (3)0.1114 (3)0.7378 (2)0.0455 (9)
C10.6483 (3)0.8203 (3)0.89055 (18)0.0256 (8)
C20.7086 (4)0.9037 (3)0.95052 (19)0.0307 (9)
H20.7499840.8958590.9934470.037*
C30.6963 (4)0.9951 (3)0.93523 (19)0.0300 (8)
H30.7272191.0636120.9652520.036*
C40.6272 (3)0.9697 (3)0.86469 (18)0.0260 (8)
C50.5972 (3)1.0441 (3)0.82930 (18)0.0239 (8)
C60.5266 (3)1.0177 (3)0.76185 (18)0.0241 (8)
C70.4909 (3)1.0933 (3)0.72672 (19)0.0262 (8)
H70.5116091.1679800.7442520.031*
C80.4224 (3)1.0379 (3)0.66416 (18)0.0250 (8)
H80.3853641.0664860.6294860.030*
C90.4153 (3)0.9279 (3)0.65924 (18)0.0229 (8)
C100.3558 (3)0.8469 (3)0.60109 (18)0.0230 (8)
C110.3521 (3)0.7413 (3)0.59601 (18)0.0234 (8)
C120.2889 (3)0.6571 (3)0.53708 (19)0.0272 (8)
H120.2446930.6640150.4949650.033*
C130.3034 (3)0.5658 (3)0.55202 (19)0.0277 (8)
H130.2712690.4967460.5225370.033*
C140.3767 (3)0.5930 (3)0.62093 (18)0.0247 (8)
C150.4094 (3)0.5189 (3)0.65521 (19)0.0250 (8)
C160.4760 (3)0.5440 (3)0.72338 (18)0.0243 (8)
C170.5094 (3)0.4684 (3)0.75952 (19)0.0284 (8)
H170.4881910.3935900.7420740.034*
C180.5764 (4)0.5228 (3)0.82292 (19)0.0297 (8)
H180.6118200.4936680.8580120.036*
C190.5840 (3)0.6333 (3)0.82736 (18)0.0258 (8)
C200.6438 (3)0.7142 (3)0.88563 (18)0.0271 (8)
C210.6423 (4)1.1597 (3)0.8654 (2)0.0323 (9)
C220.7412 (4)1.2438 (3)0.8391 (3)0.0444 (11)
H220.7807181.2275630.7982610.053*
C230.7834 (5)1.3525 (4)0.8721 (4)0.0723 (19)
H230.8511221.4101540.8540170.087*
C240.7248 (6)1.3741 (5)0.9313 (3)0.0717 (16)
H240.7521981.4473550.9540560.086*
C250.6306 (6)1.2939 (5)0.9568 (3)0.0686 (15)
H250.5924201.3112100.9979020.082*
C260.5855 (5)1.1843 (4)0.9250 (2)0.0485 (12)
H260.5175251.1280690.9440190.058*
C270.2853 (3)0.8727 (3)0.54106 (18)0.0247 (8)
C280.3384 (4)0.8999 (3)0.47622 (19)0.0302 (8)
H280.4208250.9014190.4688820.036*
C290.2716 (4)0.9249 (3)0.4221 (2)0.0349 (9)
H290.3092950.9450090.3782890.042*
C300.1512 (4)0.9207 (3)0.4314 (2)0.0375 (10)
H300.1054890.9372240.3940890.045*
C310.0966 (4)0.8924 (3)0.4957 (2)0.0371 (10)
H310.0130960.8887720.5022240.044*
C320.1641 (4)0.8694 (3)0.5501 (2)0.0313 (9)
H320.1268610.8510680.5941990.038*
C330.3693 (3)0.4058 (3)0.61587 (19)0.0263 (8)
C340.4381 (4)0.3869 (3)0.5602 (2)0.0363 (9)
H340.5136570.4450910.5492280.044*
C350.3976 (4)0.2839 (3)0.5207 (2)0.0425 (11)
H350.4445610.2722770.4821700.051*
C360.2898 (4)0.1983 (3)0.5369 (2)0.0370 (9)
H360.2622770.1277970.5097110.044*
C370.2223 (4)0.2155 (3)0.5925 (2)0.0400 (10)
H370.1482370.1563930.6041020.048*
C380.2613 (4)0.3187 (3)0.6320 (2)0.0342 (9)
H380.2136690.3296730.6702910.041*
C390.7114 (4)0.6876 (3)0.94673 (19)0.0291 (8)
C400.6449 (4)0.6311 (4)1.0004 (2)0.0426 (11)
H400.5543490.6058480.9978930.051*
C410.7092 (4)0.6107 (4)1.0582 (2)0.0492 (12)
H410.6623380.5725611.0951140.059*
C420.8383 (4)0.6449 (3)1.0622 (2)0.0389 (10)
H420.8818570.6312671.1019110.047*
C430.9051 (5)0.6988 (5)1.0089 (3)0.0668 (17)
H430.9953690.7216981.0110940.080*
C440.8421 (4)0.7206 (5)0.9513 (2)0.0626 (16)
H440.8898960.7587510.9146310.075*
C450.2690 (4)0.6167 (3)0.8338 (2)0.0342 (9)
H45A0.3393400.6295380.8710470.041*
H45B0.2658160.5576310.7962850.041*
C460.1399 (4)0.5800 (3)0.8691 (2)0.0371 (9)
H46A0.0813250.5058500.8460320.045*
H46B0.1551550.5760240.9211720.045*
C470.1698 (4)0.7664 (3)0.8940 (2)0.0364 (9)
H47A0.1868250.7649780.9462690.044*
H47B0.1309940.8197220.8890450.044*
C480.2977 (4)0.8044 (3)0.8581 (2)0.0315 (9)
H48A0.3124700.8729440.8370380.038*
H48B0.3691750.8199310.8951320.038*
C490.1853 (3)0.6960 (4)0.7466 (2)0.0359 (9)
H49A0.1804230.6375170.7081030.043*
H49B0.1988610.7629540.7238480.043*
C500.0578 (4)0.6592 (4)0.7833 (2)0.0380 (10)
H50A0.0169020.7104240.7759240.046*
H50B0.0012530.5850780.7604610.046*
C510.0607 (5)0.0037 (4)0.7062 (3)0.0498 (12)
H51A0.1278140.0119430.6724370.060*
H51B0.0237540.0351630.6782190.060*
C520.0730 (6)0.0631 (5)0.7638 (3)0.0715 (16)
H52A0.0057300.1317300.7600450.086*
H52B0.1457290.0835790.7549760.086*
C530.2081 (5)0.0972 (6)0.8398 (3)0.0713 (18)
H53A0.2847770.0809470.8347640.086*
H53B0.2182790.1397600.8879740.086*
C540.1989 (4)0.1656 (4)0.7813 (3)0.0508 (12)
H54A0.2094160.2390330.8039370.061*
H54B0.2687230.1754490.7492330.061*
C550.0164 (5)0.0252 (6)0.8457 (3)0.0781 (19)
H55A0.0042170.0666680.8944710.094*
H55B0.0973270.0413750.8426330.094*
C560.0256 (5)0.0971 (4)0.7877 (3)0.0602 (14)
H56A0.1109910.0619710.7604470.072*
H56B0.0155500.1698210.8116070.072*
C570.1392 (4)0.4445 (4)0.3826 (2)0.0523 (12)
C580.0359 (4)0.4653 (3)0.4037 (2)0.0349 (9)
H580.0259310.4135100.4290010.042*
C590.0188 (5)0.5552 (5)0.3903 (3)0.0572 (13)
H590.0544860.5651230.4056110.069*
C600.1086 (5)0.6351 (4)0.3537 (3)0.0634 (15)
H600.0972460.6987030.3432300.076*
C610.2132 (6)0.6167 (6)0.3338 (3)0.089 (2)
H610.2777610.6706800.3111880.107*
C620.2276 (4)0.5205 (5)0.3458 (2)0.0543 (13)
H620.2981630.5077440.3286150.065*
C630.1530 (6)0.3430 (4)0.3959 (3)0.0683 (16)
H63A0.1225150.3227920.4429180.102*
H63B0.2433940.3551040.3957980.102*
H63C0.1023990.2836030.3576710.102*
O10.074 (2)0.3331 (16)0.7725 (9)0.094 (6)0.25
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0264 (3)0.0240 (3)0.0171 (3)0.0120 (3)0.0008 (2)0.0046 (2)
Cl10.0300 (5)0.0331 (5)0.0276 (4)0.0127 (4)0.0072 (4)0.0076 (4)
N10.0274 (15)0.0284 (17)0.0200 (14)0.0141 (14)0.0024 (12)0.0062 (13)
N40.0276 (15)0.0269 (17)0.0210 (14)0.0124 (14)0.0027 (13)0.0048 (13)
N30.0247 (15)0.0235 (16)0.0218 (14)0.0111 (13)0.0030 (12)0.0053 (13)
N20.0249 (15)0.0238 (16)0.0207 (14)0.0109 (13)0.0003 (12)0.0018 (13)
N50.0273 (15)0.0266 (16)0.0201 (14)0.0126 (14)0.0003 (12)0.0041 (13)
N60.0319 (17)0.0373 (19)0.0305 (16)0.0159 (15)0.0066 (14)0.0108 (15)
N70.071 (3)0.090 (4)0.051 (3)0.036 (3)0.005 (2)0.034 (3)
N80.045 (2)0.050 (2)0.045 (2)0.0221 (19)0.0035 (18)0.0084 (19)
C10.0297 (18)0.033 (2)0.0178 (16)0.0152 (17)0.0037 (15)0.0077 (16)
C20.040 (2)0.038 (2)0.0180 (17)0.0197 (19)0.0003 (16)0.0066 (17)
C30.038 (2)0.034 (2)0.0191 (17)0.0169 (18)0.0012 (16)0.0009 (17)
C40.0273 (18)0.031 (2)0.0207 (17)0.0129 (17)0.0016 (15)0.0009 (16)
C50.0257 (18)0.028 (2)0.0185 (16)0.0115 (16)0.0048 (15)0.0029 (16)
C60.0248 (18)0.028 (2)0.0226 (17)0.0131 (16)0.0056 (15)0.0040 (16)
C70.0306 (19)0.025 (2)0.0243 (18)0.0129 (17)0.0025 (16)0.0037 (16)
C80.0292 (18)0.025 (2)0.0227 (17)0.0124 (16)0.0015 (15)0.0058 (16)
C90.0238 (17)0.027 (2)0.0197 (16)0.0115 (16)0.0037 (15)0.0067 (16)
C100.0224 (17)0.027 (2)0.0187 (16)0.0079 (16)0.0045 (14)0.0080 (16)
C110.0229 (17)0.028 (2)0.0184 (16)0.0093 (16)0.0011 (14)0.0040 (16)
C120.0259 (18)0.030 (2)0.0228 (17)0.0081 (17)0.0004 (15)0.0053 (17)
C130.0269 (18)0.028 (2)0.0246 (18)0.0082 (17)0.0009 (16)0.0011 (17)
C140.0229 (17)0.027 (2)0.0232 (17)0.0087 (16)0.0032 (15)0.0049 (16)
C150.0230 (17)0.027 (2)0.0267 (18)0.0103 (16)0.0079 (15)0.0067 (16)
C160.0238 (17)0.027 (2)0.0240 (17)0.0114 (16)0.0056 (15)0.0069 (16)
C170.036 (2)0.028 (2)0.0275 (18)0.0174 (18)0.0100 (17)0.0095 (17)
C180.039 (2)0.033 (2)0.0260 (18)0.0219 (18)0.0031 (17)0.0106 (17)
C190.0275 (18)0.032 (2)0.0218 (17)0.0144 (17)0.0082 (15)0.0104 (17)
C200.0314 (19)0.034 (2)0.0194 (17)0.0153 (18)0.0048 (16)0.0094 (17)
C210.040 (2)0.033 (2)0.0268 (19)0.0199 (19)0.0111 (17)0.0028 (18)
C220.041 (2)0.033 (2)0.057 (3)0.014 (2)0.011 (2)0.000 (2)
C230.059 (3)0.036 (3)0.107 (5)0.007 (3)0.044 (3)0.014 (3)
C240.0757 (18)0.0698 (18)0.0716 (18)0.0327 (11)0.0008 (10)0.0074 (10)
C250.0731 (17)0.0694 (17)0.0666 (17)0.0331 (11)0.0027 (10)0.0064 (10)
C260.090 (4)0.051 (3)0.025 (2)0.052 (3)0.003 (2)0.004 (2)
C270.0288 (18)0.0205 (19)0.0240 (17)0.0096 (16)0.0023 (15)0.0019 (16)
C280.0307 (19)0.033 (2)0.0250 (18)0.0103 (18)0.0009 (16)0.0083 (17)
C290.041 (2)0.035 (2)0.0257 (19)0.0105 (19)0.0015 (17)0.0107 (18)
C300.041 (2)0.038 (2)0.034 (2)0.017 (2)0.0102 (19)0.0080 (19)
C310.032 (2)0.042 (2)0.038 (2)0.0176 (19)0.0053 (18)0.003 (2)
C320.031 (2)0.036 (2)0.0255 (18)0.0137 (18)0.0006 (16)0.0030 (18)
C330.0256 (18)0.027 (2)0.0278 (18)0.0113 (16)0.0015 (16)0.0066 (17)
C340.030 (2)0.029 (2)0.045 (2)0.0075 (18)0.0131 (19)0.001 (2)
C350.039 (2)0.033 (2)0.050 (3)0.011 (2)0.011 (2)0.006 (2)
C360.041 (2)0.025 (2)0.042 (2)0.0120 (19)0.002 (2)0.0022 (19)
C370.038 (2)0.029 (2)0.041 (2)0.0002 (19)0.003 (2)0.009 (2)
C380.032 (2)0.035 (2)0.034 (2)0.0101 (18)0.0090 (18)0.0103 (19)
C390.040 (2)0.035 (2)0.0206 (17)0.0227 (19)0.0026 (16)0.0054 (17)
C400.036 (2)0.048 (3)0.037 (2)0.007 (2)0.0026 (19)0.020 (2)
C410.052 (3)0.047 (3)0.034 (2)0.002 (2)0.003 (2)0.024 (2)
C420.056 (3)0.043 (3)0.0257 (19)0.029 (2)0.0085 (19)0.0041 (19)
C430.053 (3)0.129 (5)0.047 (3)0.061 (3)0.012 (2)0.034 (3)
C440.050 (3)0.128 (5)0.040 (2)0.057 (3)0.022 (2)0.048 (3)
C450.037 (2)0.036 (2)0.036 (2)0.0188 (19)0.0135 (18)0.0126 (19)
C460.038 (2)0.038 (2)0.038 (2)0.015 (2)0.0080 (19)0.015 (2)
C470.037 (2)0.041 (2)0.036 (2)0.019 (2)0.0116 (18)0.008 (2)
C480.030 (2)0.036 (2)0.0296 (19)0.0154 (18)0.0070 (17)0.0013 (18)
C490.0265 (19)0.051 (3)0.0261 (19)0.0109 (19)0.0001 (16)0.0090 (19)
C500.029 (2)0.053 (3)0.032 (2)0.014 (2)0.0057 (17)0.015 (2)
C510.050 (3)0.052 (3)0.052 (3)0.026 (2)0.006 (2)0.006 (2)
C520.095 (4)0.051 (3)0.079 (4)0.040 (3)0.010 (3)0.006 (3)
C530.040 (3)0.123 (5)0.036 (3)0.017 (3)0.005 (2)0.014 (3)
C540.037 (2)0.058 (3)0.055 (3)0.017 (2)0.006 (2)0.005 (3)
C550.054 (3)0.111 (5)0.057 (3)0.019 (3)0.027 (3)0.013 (4)
C560.057 (3)0.063 (3)0.072 (3)0.034 (3)0.022 (3)0.008 (3)
C570.045 (3)0.065 (3)0.039 (2)0.020 (3)0.009 (2)0.012 (2)
C580.028 (2)0.040 (2)0.031 (2)0.0102 (19)0.0005 (17)0.0047 (19)
C590.052 (3)0.065 (3)0.053 (3)0.026 (3)0.006 (2)0.003 (3)
C600.060 (3)0.050 (3)0.069 (4)0.013 (3)0.019 (3)0.009 (3)
C610.064 (4)0.104 (5)0.052 (3)0.018 (4)0.008 (3)0.032 (4)
C620.033 (2)0.079 (4)0.040 (3)0.011 (3)0.008 (2)0.007 (3)
C630.073 (4)0.053 (3)0.076 (4)0.032 (3)0.019 (3)0.025 (3)
O10.138 (16)0.107 (14)0.069 (10)0.077 (13)0.025 (11)0.023 (10)
Geometric parameters (Å, º) top
Mn1—N32.008 (3)C29—H290.9500
Mn1—N42.019 (3)C30—C311.388 (6)
Mn1—N12.023 (3)C30—H300.9500
Mn1—N22.027 (3)C31—C321.383 (5)
Mn1—Cl12.4255 (10)C31—H310.9500
N1—C41.376 (5)C32—H320.9500
N1—C11.381 (4)C33—C381.386 (5)
N4—C191.382 (4)C33—C341.389 (5)
N4—C161.382 (5)C34—C351.386 (6)
N3—C141.384 (5)C34—H340.9500
N3—C111.385 (4)C35—C361.375 (6)
N2—C61.373 (5)C35—H350.9500
N2—C91.378 (4)C36—C371.371 (6)
N5—C481.480 (5)C36—H360.9500
N5—C451.484 (5)C37—C381.388 (6)
N5—C491.488 (4)C37—H370.9500
N6—C471.464 (5)C38—H380.9500
N6—C501.465 (5)C39—C441.375 (6)
N6—C461.471 (5)C39—C401.379 (5)
N7—C521.421 (7)C40—C411.391 (6)
N7—C531.484 (7)C40—H400.9500
N7—C551.491 (7)C41—C421.356 (6)
N8—C511.451 (6)C41—H410.9500
N8—C561.459 (6)C42—C431.361 (7)
N8—C541.484 (6)C42—H420.9500
C1—C201.396 (5)C43—C441.389 (6)
C1—C21.430 (5)C43—H430.9500
C2—C31.345 (5)C44—H440.9500
C2—H20.9500C45—C461.554 (5)
C3—C41.444 (5)C45—H45A0.9900
C3—H30.9500C45—H45B0.9900
C4—C51.392 (5)C46—H46A0.9900
C5—C61.401 (5)C46—H46B0.9900
C5—C211.497 (5)C47—C481.547 (5)
C6—C71.438 (5)C47—H47A0.9900
C7—C81.347 (5)C47—H47B0.9900
C7—H70.9500C48—H48A0.9900
C8—C91.438 (5)C48—H48B0.9900
C8—H80.9500C49—C501.552 (5)
C9—C101.389 (5)C49—H49A0.9900
C10—C111.393 (5)C49—H49B0.9900
C10—C271.501 (5)C50—H50A0.9900
C11—C121.427 (5)C50—H50B0.9900
C12—C131.354 (5)C51—C521.502 (7)
C12—H120.9500C51—H51A0.9900
C13—C141.436 (5)C51—H51B0.9900
C13—H130.9500C52—H52A0.9900
C14—C151.393 (5)C52—H52B0.9900
C15—C161.394 (5)C53—C541.521 (7)
C15—C331.496 (5)C53—H53A0.9900
C16—C171.433 (5)C53—H53B0.9900
C17—C181.351 (5)C54—H54A0.9900
C17—H170.9500C54—H54B0.9900
C18—C191.442 (5)C55—C561.546 (8)
C18—H180.9500C55—H55A0.9900
C19—C201.391 (5)C55—H55B0.9900
C20—C391.503 (5)C56—H56A0.9900
C21—C261.385 (6)C56—H56B0.9900
C21—C221.386 (6)C57—C621.378 (7)
C22—C231.403 (7)C57—C581.381 (6)
C22—H220.9500C57—C631.475 (7)
C23—C241.378 (8)C58—C591.341 (7)
C23—H230.9500C58—H580.9500
C24—C251.325 (8)C59—C601.410 (7)
C24—H240.9500C59—H590.9500
C25—C261.404 (7)C60—C611.372 (9)
C25—H250.9500C60—H600.9500
C26—H260.9500C61—C621.401 (9)
C27—C321.387 (5)C61—H610.9500
C27—C281.389 (5)C62—H620.9500
C28—C291.390 (5)C63—H63A0.9800
C28—H280.9500C63—H63B0.9800
C29—C301.375 (6)C63—H63C0.9800
N3—Mn1—N489.89 (12)C38—C33—C15121.4 (3)
N3—Mn1—N1173.48 (11)C34—C33—C15120.1 (3)
N4—Mn1—N189.87 (12)C35—C34—C33120.6 (4)
N3—Mn1—N289.66 (11)C35—C34—H34119.7
N4—Mn1—N2172.80 (11)C33—C34—H34119.7
N1—Mn1—N289.76 (12)C36—C35—C34120.4 (4)
N3—Mn1—Cl193.35 (8)C36—C35—H35119.8
N4—Mn1—Cl194.32 (9)C34—C35—H35119.8
N1—Mn1—Cl193.17 (9)C37—C36—C35119.6 (4)
N2—Mn1—Cl192.88 (9)C37—C36—H36120.2
C4—N1—C1106.3 (3)C35—C36—H36120.2
C4—N1—Mn1126.7 (2)C36—C37—C38120.5 (4)
C1—N1—Mn1126.8 (2)C36—C37—H37119.8
C19—N4—C16106.1 (3)C38—C37—H37119.8
C19—N4—Mn1126.7 (2)C33—C38—C37120.5 (4)
C16—N4—Mn1127.0 (2)C33—C38—H38119.7
C14—N3—C11105.7 (3)C37—C38—H38119.7
C14—N3—Mn1126.9 (2)C44—C39—C40118.0 (4)
C11—N3—Mn1127.4 (2)C44—C39—C20120.8 (3)
C6—N2—C9106.4 (3)C40—C39—C20121.2 (3)
C6—N2—Mn1126.6 (2)C39—C40—C41120.6 (4)
C9—N2—Mn1126.8 (2)C39—C40—H40119.7
C48—N5—C45107.8 (3)C41—C40—H40119.7
C48—N5—C49108.1 (3)C42—C41—C40120.5 (4)
C45—N5—C49107.3 (3)C42—C41—H41119.8
C47—N6—C50109.0 (3)C40—C41—H41119.8
C47—N6—C46108.1 (3)C41—C42—C43119.6 (4)
C50—N6—C46107.3 (3)C41—C42—H42120.2
C52—N7—C53108.6 (4)C43—C42—H42120.2
C52—N7—C55107.3 (4)C42—C43—C44120.4 (4)
C53—N7—C55105.4 (5)C42—C43—H43119.8
C51—N8—C56108.4 (4)C44—C43—H43119.8
C51—N8—C54108.0 (4)C39—C44—C43120.8 (4)
C56—N8—C54107.1 (4)C39—C44—H44119.6
N1—C1—C20125.8 (3)C43—C44—H44119.6
N1—C1—C2109.5 (3)N5—C45—C46110.7 (3)
C20—C1—C2124.7 (3)N5—C45—H45A109.5
C3—C2—C1107.7 (3)C46—C45—H45A109.5
C3—C2—H2126.1N5—C45—H45B109.5
C1—C2—H2126.1C46—C45—H45B109.5
C2—C3—C4107.2 (3)H45A—C45—H45B108.1
C2—C3—H3126.4N6—C46—C45111.0 (3)
C4—C3—H3126.4N6—C46—H46A109.4
N1—C4—C5126.2 (3)C45—C46—H46A109.4
N1—C4—C3109.3 (3)N6—C46—H46B109.4
C5—C4—C3124.5 (3)C45—C46—H46B109.4
C4—C5—C6124.1 (3)H46A—C46—H46B108.0
C4—C5—C21118.3 (3)N6—C47—C48111.5 (3)
C6—C5—C21117.5 (3)N6—C47—H47A109.3
N2—C6—C5126.0 (3)C48—C47—H47A109.3
N2—C6—C7109.9 (3)N6—C47—H47B109.3
C5—C6—C7124.1 (3)C48—C47—H47B109.3
C8—C7—C6106.8 (3)H47A—C47—H47B108.0
C8—C7—H7126.6N5—C48—C47110.6 (3)
C6—C7—H7126.6N5—C48—H48A109.5
C7—C8—C9107.8 (3)C47—C48—H48A109.5
C7—C8—H8126.1N5—C48—H48B109.5
C9—C8—H8126.1C47—C48—H48B109.5
N2—C9—C10126.0 (3)H48A—C48—H48B108.1
N2—C9—C8109.1 (3)N5—C49—C50110.7 (3)
C10—C9—C8124.8 (3)N5—C49—H49A109.5
C9—C10—C11124.4 (3)C50—C49—H49A109.5
C9—C10—C27118.1 (3)N5—C49—H49B109.5
C11—C10—C27117.4 (3)C50—C49—H49B109.5
N3—C11—C10125.5 (3)H49A—C49—H49B108.1
N3—C11—C12109.8 (3)N6—C50—C49111.1 (3)
C10—C11—C12124.7 (3)N6—C50—H50A109.4
C13—C12—C11107.7 (3)C49—C50—H50A109.4
C13—C12—H12126.2N6—C50—H50B109.4
C11—C12—H12126.2C49—C50—H50B109.4
C12—C13—C14107.0 (3)H50A—C50—H50B108.0
C12—C13—H13126.5N8—C51—C52111.0 (4)
C14—C13—H13126.5N8—C51—H51A109.4
N3—C14—C15126.2 (3)C52—C51—H51A109.4
N3—C14—C13109.9 (3)N8—C51—H51B109.4
C15—C14—C13123.9 (3)C52—C51—H51B109.4
C14—C15—C16124.0 (3)H51A—C51—H51B108.0
C14—C15—C33117.3 (3)N7—C52—C51113.6 (4)
C16—C15—C33118.8 (3)N7—C52—H52A108.8
N4—C16—C15125.8 (3)C51—C52—H52A108.8
N4—C16—C17109.7 (3)N7—C52—H52B108.8
C15—C16—C17124.6 (3)C51—C52—H52B108.8
C18—C17—C16107.5 (3)H52A—C52—H52B107.7
C18—C17—H17126.2N7—C53—C54111.5 (4)
C16—C17—H17126.2N7—C53—H53A109.3
C17—C18—C19107.2 (3)C54—C53—H53A109.3
C17—C18—H18126.4N7—C53—H53B109.3
C19—C18—H18126.4C54—C53—H53B109.3
N4—C19—C20126.1 (3)H53A—C53—H53B108.0
N4—C19—C18109.5 (3)N8—C54—C53110.8 (4)
C20—C19—C18124.5 (3)N8—C54—H54A109.5
C19—C20—C1124.3 (3)C53—C54—H54A109.5
C19—C20—C39118.4 (3)N8—C54—H54B109.5
C1—C20—C39117.3 (3)C53—C54—H54B109.5
C26—C21—C22119.2 (4)H54A—C54—H54B108.1
C26—C21—C5120.6 (4)N7—C55—C56110.8 (4)
C22—C21—C5120.2 (4)N7—C55—H55A109.5
C21—C22—C23120.7 (5)C56—C55—H55A109.5
C21—C22—H22119.7N7—C55—H55B109.5
C23—C22—H22119.7C56—C55—H55B109.5
C24—C23—C22118.6 (6)H55A—C55—H55B108.1
C24—C23—H23120.7N8—C56—C55110.7 (4)
C22—C23—H23120.7N8—C56—H56A109.5
C25—C24—C23120.9 (6)C55—C56—H56A109.5
C25—C24—H24119.6N8—C56—H56B109.5
C23—C24—H24119.6C55—C56—H56B109.5
C24—C25—C26122.0 (6)H56A—C56—H56B108.1
C24—C25—H25119.0C62—C57—C58117.5 (5)
C26—C25—H25119.0C62—C57—C63120.6 (5)
C21—C26—C25118.6 (5)C58—C57—C63121.9 (5)
C21—C26—H26120.7C59—C58—C57123.1 (5)
C25—C26—H26120.7C59—C58—H58118.4
C32—C27—C28118.8 (3)C57—C58—H58118.4
C32—C27—C10119.6 (3)C58—C59—C60120.6 (5)
C28—C27—C10121.6 (3)C58—C59—H59119.7
C27—C28—C29120.3 (4)C60—C59—H59119.7
C27—C28—H28119.9C61—C60—C59116.9 (5)
C29—C28—H28119.9C61—C60—H60121.5
C30—C29—C28120.4 (4)C59—C60—H60121.5
C30—C29—H29119.8C60—C61—C62121.9 (5)
C28—C29—H29119.8C60—C61—H61119.1
C29—C30—C31119.8 (4)C62—C61—H61119.1
C29—C30—H30120.1C57—C62—C61119.9 (5)
C31—C30—H30120.1C57—C62—H62120.1
C32—C31—C30119.8 (4)C61—C62—H62120.1
C32—C31—H31120.1C57—C63—H63A109.5
C30—C31—H31120.1C57—C63—H63B109.5
C31—C32—C27120.9 (4)H63A—C63—H63B109.5
C31—C32—H32119.5C57—C63—H63C109.5
C27—C32—H32119.5H63A—C63—H63C109.5
C38—C33—C34118.4 (4)H63B—C63—H63C109.5
Comparison of bond lengths and angles for structures (I)–(IV) and associated literature top
(I)(II)(III)(IV)MnClTPP (Boucher, 1972)MnClTPP-Py (Kirner & Scheidt, 1975)
Porphyrin angles (°)
N1—Mn1—N3179.75 (9)173.58 (5)173.4 (1)166.9 (3)172.8 (2)
N2—Mn1—N4178.75 (8)173.32 (5)172.8 (1)161.7 (3)173.6 (2)
N1—Mn1—N1A180.00 (15)
N2—Mn1—N2A180.00 (11)
Ligand–Mn1–ligand angles (°)
N5—Mn1—N7178.65 (7)
N3—Mn1—N3A180.00 (11)
N5—Mn1—Cl1175.43 (3)179.41 (6)175.5 (1)
Ruffle angles (°)
C1C5—N1—C15C20—N4
C5C9—N2—C10C15—N35.64 (5)19.66 (3)1.63 (9)
C5C9—N2—C10—C11AC5A—N1A
C5C1—N1—C10—C10AC5A—N2A0.00 (4)
C20—C1C4—N1—C5C10—N2
C10C14—N3—C15C20—N46.79 (5)21.66 (4)0.42 (7)
C10A—C1C4—N1—C5C10-N2
C10—C1AC4A—N1A—C5AC10A-N2A0.00 (0)
`Swayback' angles (°)
C27—C10—Mn1
C39—C20—Mn11.64 (9)6.34 (7)3.0 (2)
C17—C10—Mn1
C17A—C10A—Mn10.00 (6)
C11—C5—Mn1
C11A—C5A—Mn10.00 (6)
C21—C5—Mn1
C33—C15—Mn16.27 (9)3.07 (8)1.78 (4)
Phenyl angles to porphyrin ring (°)
C21C2666.87 (7)60.40 (4)72.61 (8)54.259.8
C27C3288.75 (7)67.95 (3)80.6 (1)123.579.1
C33C3877.94 (7)61.72 (4)79.51 (8)49.769.1
C39C4464.48 (8)74.79 (3)80.29 (11)77.472
C11C1670.13 (7)
C17C2264.49 (6)
Mn1-to-ligand distances (Å)
Mn1—N12.018 (2)2.0199 (17)2.0124 (12)2.022 (3)1.999 (7)2.022 (4)
Mn1—N22.025 (2)2.0164 (17)2.0060 (12)2.026 (3)2.0212 (7)2.006 (4)
Mn1—N32.025 (2)2.3704 (17)2.0083 (12)2.007 (2)1.992 (7)2.010 (3)
Mn1—N42.015 (2)2.0025 (12)2.019 (3)2.022 (7)2.000 (4)
Mn1—N52.285 (2)2.4203 (12)2.612 (3)2.444 (4)
Mn1—N72.284 (2)
Mn1—Cl12.4693 (4)2.4253 (9)2.363 (3)2.467 (1)
Mn atom displacement from the N1/N2/N3/N4 plane (Å)-0.0075 (8)0.0000 (0)-0.0913 (5)-0.097 (1)0.270.145
Plane N1/N2/N3/N4/Mn1 versus Cl1 angle (°)93.77 (6)93.44 (14)4.7 (175.3)
Plane N1/N2/N3/N4/Mn1 versus N5 angle (°)86.73 (8)86.56 (18)
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds