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The crystal structure of solvated [Mn(TPP)(NO3)] (TPP = 5,10,15,20-tetra­phenyl­porphyrinato, C44H28N4), [Mn(C44H28N4O3)(NO3)]·0.5C6H14·0.5C6H6, has been determined in the space group Pccn. The MnIII atom has a distorted square-pyramidal environment, being coordinated by four pyrrole N atoms of the porphyrin ligand in the basal plane and an O atom of the nitrato ligand in the apical site. The MnIII atom is displaced out of the porphyrin plane by 0.22 (4) Å with the average Mn—Np distance being 2.011 (6) Å (where Np is a porphyrin N atom). The Mn—O bond length is 2.1246 (18) Å. Two kinds of inter­molecular C—H...O hydrogen bonds exist in the crystal structure, with the apical nitrato ligands inter­acting with solvent mol­ecules and adjacent mol­ecules, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314622003868/wm4162sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314622003868/wm4162Isup3.hkl
Contains datablock I

CCDC reference: 2165166

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in solvent or counterion
  • R factor = 0.050
  • wR factor = 0.148
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C SHFSU01_ALERT_2_C The absolute value of parameter shift to su ratio > 0.05 Absolute value of the parameter shift to su ratio given 0.097 Additional refinement cycles may be required. PLAT080_ALERT_2_C Maximum Shift/Error ............................ 0.10 Why ? PLAT220_ALERT_2_C NonSolvent Resd 1 C Ueq(max)/Ueq(min) Range 3.6 Ratio PLAT331_ALERT_2_C Small Aver Phenyl C-C Dist C4S --C9S . 1.36 Ang. PLAT332_ALERT_2_C Large Phenyl C-C Range C4S -C9S . 0.16 Ang. PLAT715_ALERT_1_C D-H Unknown or Inconsistent Label .......... 4S Check PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ... -0.227 Report PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 8 Report PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 6 Note
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 2 Note PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large 10.12 Why ? PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 1 Report PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report PLAT300_ALERT_4_G Atom Site Occupancy of C4S Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of C5S Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of C6S Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of C7S Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of C8S Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of C9S Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H4S Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H5S Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H6S Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H7S Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H8S Constrained at 0.5 Check PLAT300_ALERT_4_G Atom Site Occupancy of H9S Constrained at 0.5 Check PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd 3 ) 100% Note PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 35 Note PLAT789_ALERT_4_G Atoms with Negative _atom_site_disorder_group # 12 Check PLAT794_ALERT_5_G Tentative Bond Valency for Mn1 (III) . 2.87 Info PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 37 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 4 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 8 Note PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File 1 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 13 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 9 ALERT level C = Check. Ensure it is not caused by an omission or oversight 25 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 18 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Nitrato(5,10,15,20-tetraphenylporphinato)manganese(III)–benzene–n-hexane (2/1/1) top
Crystal data top
[Mn(C44H28N4O3)(NO3)]·0.5C6H14·0.5C6H6Dx = 1.384 Mg m3
Mr = 811.79Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PccnCell parameters from 9845 reflections
a = 20.1021 (10) Åθ = 2.5–26.7°
b = 21.5505 (9) ŵ = 0.39 mm1
c = 17.9807 (9) ÅT = 100 K
V = 7789.4 (6) Å3Block, black
Z = 80.33 × 0.29 × 0.12 mm
F(000) = 3376
Data collection top
Bruker APEXII CCD
diffractometer
6163 reflections with I > 2σ(I)
φ and ω scansRint = 0.058
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
θmax = 26.7°, θmin = 2.3°
Tmin = 0.763, Tmax = 0.865h = 2523
58775 measured reflectionsk = 2724
8270 independent reflectionsl = 2221
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.148 w = 1/[σ2(Fo2) + (0.0686P)2 + 10.1161P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.097
8270 reflectionsΔρmax = 0.80 e Å3
560 parametersΔρmin = 0.48 e Å3
37 restraints
Special details top

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)
Mn10.42182 (2)0.50321 (2)0.38016 (2)0.01235 (11)
O10.42711 (8)0.52498 (8)0.26507 (10)0.0206 (4)
O20.41592 (10)0.58633 (9)0.17166 (11)0.0311 (5)
O30.42351 (12)0.62345 (10)0.28275 (12)0.0416 (6)
N10.49166 (9)0.43691 (8)0.36975 (11)0.0144 (4)
N20.35071 (9)0.43777 (8)0.36889 (11)0.0148 (4)
N30.35138 (9)0.56361 (9)0.41173 (11)0.0151 (4)
N40.49211 (9)0.56102 (8)0.41874 (11)0.0147 (4)
N50.42152 (11)0.57920 (11)0.23960 (13)0.0259 (5)
C10.42051 (11)0.28091 (11)0.31319 (15)0.0183 (5)
C20.44918 (13)0.23571 (11)0.35761 (16)0.0259 (6)
H20.4679630.2470130.4041590.031*
C30.45086 (14)0.17416 (12)0.33504 (18)0.0304 (6)
H30.4705780.1436100.3661080.036*
C40.42397 (14)0.15745 (12)0.26773 (19)0.0341 (7)
H40.4256150.1153940.2519820.041*
C50.39436 (16)0.20192 (13)0.22261 (18)0.0369 (7)
H50.3755090.1902710.1762180.044*
C60.39240 (14)0.26347 (12)0.24550 (16)0.0298 (6)
H60.3717940.2938050.2148580.036*
C70.17559 (12)0.50079 (10)0.38931 (13)0.0158 (5)
C80.14138 (12)0.47327 (11)0.44853 (15)0.0198 (5)
H80.1655230.4565730.4893060.024*
C90.07229 (12)0.47019 (12)0.44807 (16)0.0243 (6)
H90.0493400.4513400.4883580.029*
C100.03678 (13)0.49480 (12)0.38843 (15)0.0244 (6)
H100.0104190.4927040.3878560.029*
C110.07056 (13)0.52232 (13)0.33002 (16)0.0256 (6)
H110.0463530.5392090.2894020.031*
C120.13958 (12)0.52542 (11)0.33034 (15)0.0217 (5)
H120.1622740.5444800.2900160.026*
C130.42453 (11)0.72160 (11)0.45726 (15)0.0189 (5)
C140.45003 (16)0.75859 (13)0.4016 (2)0.0404 (8)
H140.4665600.7402720.3572130.048*
C150.45157 (18)0.82290 (14)0.4103 (2)0.0527 (10)
H150.4689770.8480520.3715150.063*
C160.42877 (14)0.84987 (13)0.4729 (2)0.0398 (8)
H160.4294180.8937610.4778000.048*
C170.40443 (17)0.81338 (14)0.5299 (2)0.0430 (9)
H170.3896090.8321240.5747260.052*
C180.40157 (16)0.74907 (13)0.52169 (17)0.0338 (7)
H180.3838010.7241570.5604870.041*
C190.66708 (12)0.50305 (10)0.38165 (13)0.0154 (5)
C200.70957 (12)0.45885 (11)0.41236 (14)0.0198 (5)
H200.6919670.4265730.4424830.024*
C210.77752 (13)0.46181 (13)0.39912 (15)0.0256 (6)
H210.8060870.4312610.4198720.031*
C220.80410 (13)0.50902 (13)0.35582 (16)0.0271 (6)
H220.8506470.5108650.3469560.032*
C230.76238 (13)0.55324 (13)0.32574 (15)0.0277 (6)
H230.7803810.5858430.2964270.033*
C240.69414 (13)0.55040 (12)0.33805 (15)0.0226 (5)
H240.6657770.5808210.3166930.027*
C(A10.55989 (11)0.44641 (10)0.36743 (13)0.0146 (5)
C(A20.48166 (12)0.37726 (10)0.34335 (13)0.0157 (5)
C(A30.35993 (12)0.37606 (10)0.35121 (14)0.0169 (5)
C(A40.28251 (12)0.44579 (10)0.37543 (13)0.0159 (5)
C(A50.28327 (12)0.55656 (11)0.40428 (14)0.0174 (5)
C(A60.36142 (12)0.62527 (10)0.43015 (14)0.0173 (5)
C(A70.48260 (12)0.62090 (10)0.44399 (13)0.0162 (5)
C(A80.56024 (11)0.55124 (10)0.42006 (13)0.0150 (5)
C(B10.59185 (12)0.39247 (11)0.33697 (14)0.0194 (5)
H(B10.6381680.3875140.3283210.023*
C(B20.54403 (12)0.35015 (11)0.32289 (14)0.0191 (5)
H(B20.5505610.3097480.3030400.023*
C(B30.29657 (12)0.34533 (11)0.34796 (15)0.0216 (5)
H(B30.2893100.3026520.3375010.026*
C(B40.24941 (12)0.38788 (11)0.36239 (15)0.0213 (5)
H(B40.2027620.3808780.3637120.026*
C(B50.25083 (13)0.61474 (11)0.41847 (15)0.0230 (6)
H(B50.2042570.6222000.4177280.028*
C(B60.29864 (12)0.65671 (11)0.43303 (16)0.0230 (6)
H(B60.2919820.6994960.4433610.028*
C(B70.54509 (12)0.64704 (11)0.46568 (14)0.0182 (5)
H(B70.5519680.6872120.4860430.022*
C(B80.59258 (12)0.60410 (11)0.45188 (14)0.0176 (5)
H(B80.6388330.6082550.4615250.021*
C(M10.42063 (12)0.34755 (10)0.33679 (13)0.0162 (5)
C(M20.25010 (12)0.50150 (10)0.38919 (13)0.0153 (5)
C(M30.42232 (11)0.65274 (10)0.44520 (14)0.0168 (5)
C(M40.59319 (12)0.49958 (10)0.39124 (13)0.0145 (5)
C1S0.28678 (18)0.23978 (17)0.4985 (2)0.0488 (9)
H1SA0.3152640.2763550.5082790.059*
H1SB0.2983930.2235350.4486470.059*
C2S0.30152 (18)0.18932 (17)0.5575 (2)0.0509 (9)
H2SA0.2890870.2049760.6073360.061*
H2SB0.2742820.1520720.5469550.061*
C3S0.37423 (19)0.17186 (17)0.5572 (2)0.0571 (10)
H3SA0.3875120.1597870.5067610.086*
H3SB0.3815070.1369960.5912020.086*
H3SC0.4008950.2074610.5733410.086*
C4S0.3238 (4)0.7350 (3)0.2525 (4)0.0454 (15)0.5
H4S0.3635430.7183010.2729520.054*0.5
C5S0.2861 (11)0.7015 (10)0.2020 (13)0.069 (6)0.5
H5S0.2993100.6603020.1905090.083*0.5
C6S0.2325 (5)0.7245 (4)0.1690 (6)0.077 (3)0.5
H6S0.2102170.7019100.1311130.093*0.5
C7S0.2079 (11)0.7868 (11)0.1930 (17)0.075 (6)0.5
H7S0.1678380.8039040.1739350.090*0.5
C8S0.2462 (4)0.8181 (4)0.2438 (5)0.0518 (19)0.5
H8S0.2330130.8583910.2592700.062*0.5
C9S0.3018 (3)0.7930 (3)0.2721 (4)0.0414 (15)0.5
H9S0.3268620.8162920.3070850.050*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.01075 (19)0.00928 (18)0.0170 (2)0.00011 (12)0.00051 (13)0.00002 (13)
O10.0168 (9)0.0267 (9)0.0183 (9)0.0015 (7)0.0016 (7)0.0008 (7)
O20.0329 (11)0.0353 (11)0.0252 (11)0.0007 (8)0.0020 (8)0.0095 (9)
O30.0610 (15)0.0309 (11)0.0328 (12)0.0039 (10)0.0025 (10)0.0002 (9)
N10.0149 (10)0.0101 (9)0.0181 (10)0.0004 (7)0.0014 (8)0.0002 (8)
N20.0134 (10)0.0104 (9)0.0206 (11)0.0001 (7)0.0007 (8)0.0002 (8)
N30.0117 (9)0.0115 (9)0.0220 (11)0.0004 (7)0.0000 (8)0.0009 (8)
N40.0149 (10)0.0100 (9)0.0191 (11)0.0013 (7)0.0001 (8)0.0005 (8)
N50.0201 (11)0.0309 (12)0.0268 (13)0.0047 (9)0.0010 (9)0.0002 (10)
C10.0126 (11)0.0137 (11)0.0286 (14)0.0017 (9)0.0024 (10)0.0036 (10)
C20.0255 (14)0.0180 (12)0.0342 (15)0.0028 (10)0.0041 (12)0.0024 (11)
C30.0262 (14)0.0138 (12)0.0511 (19)0.0033 (10)0.0036 (13)0.0017 (12)
C40.0252 (14)0.0164 (13)0.061 (2)0.0002 (11)0.0031 (14)0.0159 (13)
C50.0428 (18)0.0290 (15)0.0390 (18)0.0024 (13)0.0086 (14)0.0149 (13)
C60.0345 (15)0.0233 (14)0.0317 (16)0.0017 (11)0.0060 (13)0.0038 (11)
C70.0138 (11)0.0128 (11)0.0209 (12)0.0001 (8)0.0010 (9)0.0044 (9)
C80.0176 (12)0.0173 (12)0.0247 (13)0.0006 (9)0.0012 (10)0.0000 (10)
C90.0196 (13)0.0219 (13)0.0313 (15)0.0043 (10)0.0077 (11)0.0043 (11)
C100.0120 (12)0.0269 (14)0.0343 (16)0.0011 (10)0.0009 (10)0.0107 (11)
C110.0172 (13)0.0303 (14)0.0293 (15)0.0033 (10)0.0036 (11)0.0083 (12)
C120.0183 (13)0.0225 (12)0.0243 (14)0.0032 (10)0.0001 (10)0.0005 (10)
C130.0128 (11)0.0130 (11)0.0309 (14)0.0013 (9)0.0068 (10)0.0024 (10)
C140.0412 (18)0.0175 (14)0.062 (2)0.0008 (12)0.0178 (16)0.0018 (14)
C150.044 (2)0.0170 (14)0.097 (3)0.0012 (13)0.024 (2)0.0097 (17)
C160.0225 (14)0.0127 (12)0.084 (3)0.0005 (11)0.0136 (15)0.0049 (15)
C170.052 (2)0.0296 (16)0.048 (2)0.0194 (14)0.0259 (16)0.0189 (15)
C180.0496 (18)0.0196 (13)0.0321 (16)0.0122 (12)0.0080 (14)0.0017 (12)
C190.0130 (11)0.0159 (11)0.0173 (12)0.0024 (9)0.0003 (9)0.0027 (9)
C200.0194 (13)0.0184 (12)0.0216 (13)0.0013 (9)0.0010 (10)0.0002 (10)
C210.0183 (13)0.0278 (14)0.0308 (15)0.0066 (10)0.0019 (11)0.0055 (11)
C220.0155 (13)0.0340 (15)0.0317 (15)0.0039 (10)0.0045 (11)0.0089 (12)
C230.0241 (14)0.0313 (14)0.0276 (14)0.0080 (11)0.0063 (11)0.0013 (12)
C240.0212 (13)0.0217 (13)0.0249 (14)0.0017 (10)0.0010 (10)0.0026 (10)
C(A10.0141 (11)0.0130 (11)0.0167 (12)0.0011 (8)0.0011 (9)0.0022 (9)
C(A20.0184 (12)0.0117 (10)0.0171 (12)0.0026 (9)0.0004 (9)0.0006 (9)
C(A30.0170 (12)0.0122 (11)0.0214 (13)0.0010 (9)0.0021 (10)0.0002 (9)
C(A40.0148 (11)0.0143 (11)0.0185 (12)0.0012 (9)0.0007 (9)0.0010 (9)
C(A50.0150 (12)0.0139 (11)0.0232 (13)0.0020 (9)0.0011 (10)0.0011 (9)
C(A60.0165 (12)0.0126 (11)0.0227 (13)0.0011 (9)0.0008 (10)0.0011 (9)
C(A70.0167 (12)0.0127 (11)0.0191 (12)0.0001 (9)0.0012 (9)0.0002 (9)
C(A80.0132 (11)0.0139 (11)0.0180 (12)0.0005 (8)0.0014 (9)0.0016 (9)
C(B10.0176 (12)0.0161 (11)0.0245 (14)0.0023 (9)0.0023 (10)0.0003 (10)
C(B20.0182 (12)0.0133 (11)0.0258 (13)0.0031 (9)0.0009 (10)0.0029 (10)
C(B30.0175 (12)0.0138 (11)0.0336 (15)0.0041 (9)0.0002 (11)0.0024 (10)
C(B40.0149 (12)0.0170 (11)0.0320 (15)0.0030 (9)0.0005 (10)0.0003 (10)
C(B50.0147 (12)0.0158 (11)0.0386 (16)0.0022 (9)0.0011 (11)0.0022 (11)
C(B60.0162 (12)0.0141 (11)0.0386 (16)0.0024 (9)0.0017 (11)0.0025 (11)
C(B70.0192 (12)0.0131 (11)0.0224 (13)0.0021 (9)0.0011 (10)0.0018 (9)
C(B80.0156 (12)0.0170 (11)0.0202 (13)0.0011 (9)0.0021 (9)0.0007 (9)
C(M10.0179 (12)0.0112 (10)0.0196 (13)0.0007 (9)0.0016 (9)0.0001 (9)
C(M20.0135 (11)0.0149 (11)0.0175 (12)0.0002 (9)0.0002 (9)0.0025 (9)
C(M30.0173 (12)0.0114 (10)0.0215 (13)0.0006 (9)0.0012 (10)0.0003 (9)
C(M40.0119 (11)0.0145 (11)0.0170 (12)0.0007 (8)0.0007 (8)0.0019 (9)
C1S0.059 (2)0.0438 (19)0.043 (2)0.0006 (17)0.0063 (17)0.0030 (16)
C2S0.049 (2)0.046 (2)0.057 (2)0.0065 (16)0.0016 (18)0.0077 (17)
C3S0.060 (2)0.045 (2)0.067 (3)0.0008 (18)0.001 (2)0.0046 (18)
C4S0.050 (4)0.048 (4)0.038 (4)0.001 (3)0.003 (3)0.004 (3)
C5S0.074 (10)0.046 (7)0.087 (12)0.001 (6)0.014 (9)0.015 (8)
C6S0.068 (6)0.060 (5)0.104 (8)0.016 (4)0.024 (5)0.012 (5)
C7S0.046 (7)0.077 (9)0.103 (11)0.010 (6)0.043 (7)0.015 (8)
C8S0.044 (4)0.053 (4)0.059 (5)0.001 (3)0.006 (4)0.011 (4)
C9S0.042 (3)0.044 (3)0.038 (4)0.004 (3)0.006 (3)0.001 (3)
Geometric parameters (Å, º) top
Mn1—O12.1246 (18)C21—H210.9500
Mn1—N12.0119 (19)C21—C221.388 (4)
Mn1—N22.0184 (19)C22—H220.9500
Mn1—N32.0052 (19)C22—C231.380 (4)
Mn1—N42.0074 (19)C23—H230.9500
O1—N51.260 (3)C23—C241.391 (4)
O2—N51.236 (3)C24—H240.9500
O3—N51.230 (3)C(A1—C(B11.437 (3)
N1—C(A11.387 (3)C(A1—C(M41.394 (3)
N1—C(A21.385 (3)C(A2—C(B21.431 (3)
N2—C(A31.380 (3)C(A2—C(M11.389 (3)
N2—C(A41.387 (3)C(A3—C(B31.437 (3)
N3—C(A51.384 (3)C(A3—C(M11.391 (3)
N3—C(A61.384 (3)C(A4—C(B41.434 (3)
N4—C(A71.381 (3)C(A4—C(M21.388 (3)
N4—C(A81.386 (3)C(A5—C(B51.436 (3)
C1—C21.385 (4)C(A5—C(M21.388 (3)
C1—C61.394 (4)C(A6—C(B61.433 (3)
C1—C(M11.497 (3)C(A6—C(M31.386 (3)
C2—H20.9500C(A7—C(B71.431 (3)
C2—C31.388 (3)C(A7—C(M31.393 (3)
C3—H30.9500C(A8—C(B81.431 (3)
C3—C41.374 (4)C(A8—C(M41.395 (3)
C4—H40.9500C(B1—H(B10.9500
C4—C51.390 (4)C(B1—C(B21.349 (3)
C5—H50.9500C(B2—H(B20.9500
C5—C61.389 (4)C(B3—H(B30.9500
C6—H60.9500C(B3—C(B41.344 (3)
C7—C81.399 (3)C(B4—H(B40.9500
C7—C121.389 (3)C(B5—H(B50.9500
C7—C(M21.498 (3)C(B5—C(B61.346 (3)
C8—H80.9500C(B6—H(B60.9500
C8—C91.391 (3)C(B7—H(B70.9500
C9—H90.9500C(B7—C(B81.353 (3)
C9—C101.393 (4)C(B8—H(B80.9500
C10—H100.9500C1S—C1Si1.543 (7)
C10—C111.384 (4)C1S—H1SA0.9900
C11—H110.9500C1S—H1SB0.9900
C11—C121.389 (4)C1S—C2S1.548 (5)
C12—H120.9500C2S—H2SA0.9900
C13—C141.379 (4)C2S—H2SB0.9900
C13—C181.380 (4)C2S—C3S1.509 (5)
C13—C(M31.500 (3)C3S—H3SA0.9800
C14—H140.9500C3S—H3SB0.9800
C14—C151.395 (4)C3S—H3SC0.9800
C15—H150.9500C4S—H4S0.9500
C15—C161.347 (5)C4S—C5S1.38 (2)
C16—H160.9500C4S—C9S1.372 (9)
C16—C171.381 (5)C5S—H5S0.9500
C17—H170.9500C5S—C6S1.33 (2)
C17—C181.395 (4)C6S—H6S0.9500
C18—H180.9500C6S—C7S1.49 (3)
C19—C201.393 (3)C7S—H7S0.9500
C19—C241.397 (3)C7S—C8S1.37 (2)
C19—C(M41.497 (3)C8S—H8S0.9500
C20—H200.9500C8S—C9S1.342 (10)
C20—C211.388 (4)C9S—H9S0.9500
N1—Mn1—O191.79 (7)C23—C24—H24119.8
N1—Mn1—N289.34 (8)N1—C(A1—C(B1109.5 (2)
N2—Mn1—O195.27 (7)N1—C(A1—C(M4125.9 (2)
N3—Mn1—O199.66 (7)C(M4—C(A1—C(B1124.6 (2)
N3—Mn1—N1168.53 (8)N1—C(A2—C(B2109.9 (2)
N3—Mn1—N288.96 (8)N1—C(A2—C(M1125.8 (2)
N3—Mn1—N489.79 (8)C(M1—C(A2—C(B2124.3 (2)
N4—Mn1—O199.46 (7)N2—C(A3—C(B3109.5 (2)
N4—Mn1—N188.95 (8)N2—C(A3—C(M1125.9 (2)
N4—Mn1—N2165.21 (8)C(M1—C(A3—C(B3124.5 (2)
N5—O1—Mn1123.66 (15)N2—C(A4—C(B4109.7 (2)
C(A1—N1—Mn1126.01 (15)N2—C(A4—C(M2125.9 (2)
C(A2—N1—Mn1126.15 (15)C(M2—C(A4—C(B4124.3 (2)
C(A2—N1—C(A1105.67 (18)N3—C(A5—C(B5109.7 (2)
C(A3—N2—Mn1126.98 (16)N3—C(A5—C(M2126.0 (2)
C(A3—N2—C(A4105.81 (19)C(M2—C(A5—C(B5124.3 (2)
C(A4—N2—Mn1127.19 (15)N3—C(A6—C(B6109.5 (2)
C(A5—N3—Mn1126.86 (16)N3—C(A6—C(M3125.8 (2)
C(A6—N3—Mn1126.00 (15)C(M3—C(A6—C(B6124.6 (2)
C(A6—N3—C(A5105.82 (18)N4—C(A7—C(B7109.6 (2)
C(A7—N4—Mn1126.58 (15)N4—C(A7—C(M3125.9 (2)
C(A7—N4—C(A8105.85 (18)C(M3—C(A7—C(B7124.4 (2)
C(A8—N4—Mn1127.38 (15)N4—C(A8—C(B8109.6 (2)
O2—N5—O1118.8 (2)N4—C(A8—C(M4125.7 (2)
O3—N5—O1119.1 (2)C(M4—C(A8—C(B8124.6 (2)
O3—N5—O2122.0 (2)C(A1—C(B1—H(B1126.3
C2—C1—C6118.9 (2)C(B2—C(B1—C(A1107.5 (2)
C2—C1—C(M1120.7 (2)C(B2—C(B1—H(B1126.3
C6—C1—C(M1120.5 (2)C(A2—C(B2—H(B2126.3
C1—C2—H2119.5C(B1—C(B2—C(A2107.4 (2)
C1—C2—C3120.9 (3)C(B1—C(B2—H(B2126.3
C3—C2—H2119.5C(A3—C(B3—H(B3126.2
C2—C3—H3120.0C(B4—C(B3—C(A3107.6 (2)
C4—C3—C2119.9 (3)C(B4—C(B3—H(B3126.2
C4—C3—H3120.0C(A4—C(B4—H(B4126.3
C3—C4—H4119.9C(B3—C(B4—C(A4107.3 (2)
C3—C4—C5120.1 (2)C(B3—C(B4—H(B4126.3
C5—C4—H4119.9C(A5—C(B5—H(B5126.4
C4—C5—H5120.1C(B6—C(B5—C(A5107.3 (2)
C6—C5—C4119.9 (3)C(B6—C(B5—H(B5126.4
C6—C5—H5120.1C(A6—C(B6—H(B6126.1
C1—C6—H6119.8C(B5—C(B6—C(A6107.7 (2)
C5—C6—C1120.3 (3)C(B5—C(B6—H(B6126.2
C5—C6—H6119.8C(A7—C(B7—H(B7126.3
C8—C7—C(M2119.8 (2)C(B8—C(B7—C(A7107.5 (2)
C12—C7—C8119.1 (2)C(B8—C(B7—H(B7126.3
C12—C7—C(M2121.1 (2)C(A8—C(B8—H(B8126.3
C7—C8—H8119.8C(B7—C(B8—C(A8107.3 (2)
C9—C8—C7120.4 (2)C(B7—C(B8—H(B8126.3
C9—C8—H8119.8C(A2—C(M1—C1117.9 (2)
C8—C9—H9120.1C(A2—C(M1—C(A3123.7 (2)
C8—C9—C10119.9 (2)C(A3—C(M1—C1118.4 (2)
C10—C9—H9120.1C(A4—C(M2—C7117.4 (2)
C9—C10—H10120.1C(A5—C(M2—C7119.3 (2)
C11—C10—C9119.7 (2)C(A5—C(M2—C(A4123.3 (2)
C11—C10—H10120.1C(A6—C(M3—C13118.5 (2)
C10—C11—H11119.8C(A6—C(M3—C(A7123.7 (2)
C10—C11—C12120.5 (3)C(A7—C(M3—C13117.6 (2)
C12—C11—H11119.8C(A1—C(M4—C19118.8 (2)
C7—C12—H12119.8C(A1—C(M4—C(A8122.8 (2)
C11—C12—C7120.3 (2)C(A8—C(M4—C19118.3 (2)
C11—C12—H12119.8C1Si—C1S—H1SA109.1
C14—C13—C18119.1 (2)C1Si—C1S—H1SB109.1
C14—C13—C(M3118.5 (2)C1Si—C1S—C2S112.6 (3)
C18—C13—C(M3122.4 (2)H1SA—C1S—H1SB107.8
C13—C14—H14120.0C2S—C1S—H1SA109.1
C13—C14—C15120.1 (3)C2S—C1S—H1SB109.1
C15—C14—H14120.0C1S—C2S—H2SA109.4
C14—C15—H15119.5C1S—C2S—H2SB109.4
C16—C15—C14121.0 (3)H2SA—C2S—H2SB108.0
C16—C15—H15119.5C3S—C2S—C1S111.0 (3)
C15—C16—H16120.2C3S—C2S—H2SA109.4
C15—C16—C17119.6 (3)C3S—C2S—H2SB109.4
C17—C16—H16120.2C2S—C3S—H3SA109.5
C16—C17—H17119.9C2S—C3S—H3SB109.5
C16—C17—C18120.1 (3)C2S—C3S—H3SC109.5
C18—C17—H17119.9H3SA—C3S—H3SB109.5
C13—C18—C17120.1 (3)H3SA—C3S—H3SC109.5
C13—C18—H18120.0H3SB—C3S—H3SC109.5
C17—C18—H18120.0C5S—C4S—H4S121.1
C20—C19—C24118.9 (2)C5S—C4S—C9S117.8 (11)
C20—C19—C(M4121.9 (2)C9S—C4S—H4S121.1
C24—C19—C(M4119.2 (2)C4S—C5S—H5S118.5
C19—C20—H20119.9C6S—C5S—C4S122.9 (16)
C21—C20—C19120.3 (2)C6S—C5S—H5S118.6
C21—C20—H20119.9C5S—C6S—H6S120.8
C20—C21—H21119.7C5S—C6S—C7S118.4 (12)
C22—C21—C20120.6 (2)C7S—C6S—H6S120.8
C22—C21—H21119.7C6S—C7S—H7S121.6
C21—C22—H22120.3C8S—C7S—C6S116.7 (14)
C23—C22—C21119.5 (2)C8S—C7S—H7S121.7
C23—C22—H22120.3C7S—C8S—H8S119.3
C22—C23—H23119.8C9S—C8S—C7S121.5 (11)
C22—C23—C24120.4 (2)C9S—C8S—H8S119.3
C24—C23—H23119.8C4S—C9S—H9S118.7
C19—C24—H24119.8C8S—C9S—C4S122.6 (7)
C23—C24—C19120.4 (2)C8S—C9S—H9S118.7
Mn1—O1—N5—O2169.95 (16)C18—C13—C(M3—C(A7110.9 (3)
Mn1—O1—N5—O311.9 (3)C19—C20—C21—C220.6 (4)
Mn1—N1—C(A1—C(B1162.14 (16)C20—C19—C24—C230.1 (4)
Mn1—N1—C(A1—C(M418.3 (3)C20—C19—C(M4—C(A157.4 (3)
Mn1—N1—C(A2—C(B2162.58 (16)C20—C19—C(M4—C(A8125.9 (2)
Mn1—N1—C(A2—C(M117.0 (3)C20—C21—C22—C230.1 (4)
Mn1—N2—C(A3—C(B3179.46 (17)C21—C22—C23—C240.6 (4)
Mn1—N2—C(A3—C(M10.9 (4)C22—C23—C24—C190.6 (4)
Mn1—N2—C(A4—C(B4179.21 (16)C24—C19—C20—C210.5 (4)
Mn1—N2—C(A4—C(M21.9 (4)C24—C19—C(M4—C(A1119.8 (2)
Mn1—N3—C(A5—C(B5167.60 (17)C24—C19—C(M4—C(A856.8 (3)
Mn1—N3—C(A5—C(M215.5 (4)C(A1—N1—C(A2—C(B21.3 (3)
Mn1—N3—C(A6—C(B6166.81 (17)C(A1—N1—C(A2—C(M1179.1 (2)
Mn1—N3—C(A6—C(M314.5 (4)C(A1—C(B1—C(B2—C(A20.8 (3)
Mn1—N4—C(A7—C(B7179.11 (16)C(A2—N1—C(A1—C(B11.8 (3)
Mn1—N4—C(A7—C(M32.0 (4)C(A2—N1—C(A1—C(M4177.7 (2)
Mn1—N4—C(A8—C(B8179.77 (16)C(A3—N2—C(A4—C(B40.7 (3)
Mn1—N4—C(A8—C(M43.1 (3)C(A3—N2—C(A4—C(M2176.7 (2)
N1—C(A1—C(B1—C(B21.6 (3)C(A3—C(B3—C(B4—C(A40.4 (3)
N1—C(A1—C(M4—C19177.4 (2)C(A4—N2—C(A3—C(B30.9 (3)
N1—C(A1—C(M4—C(A81.0 (4)C(A4—N2—C(A3—C(M1177.6 (2)
N1—C(A2—C(B2—C(B10.4 (3)C(A5—N3—C(A6—C(B60.8 (3)
N1—C(A2—C(M1—C1174.8 (2)C(A5—N3—C(A6—C(M3177.9 (2)
N1—C(A2—C(M1—C(A34.9 (4)C(A5—C(B5—C(B6—C(A61.5 (3)
N2—C(A3—C(B3—C(B40.9 (3)C(A6—N3—C(A5—C(B50.1 (3)
N2—C(A3—C(M1—C1175.7 (2)C(A6—N3—C(A5—C(M2177.1 (2)
N2—C(A3—C(M1—C(A24.6 (4)C(A7—N4—C(A8—C(B84.5 (3)
N2—C(A4—C(B4—C(B30.2 (3)C(A7—N4—C(A8—C(M4172.3 (2)
N2—C(A4—C(M2—C7176.1 (2)C(A7—C(B7—C(B8—C(A81.1 (3)
N2—C(A4—C(M2—C(A55.4 (4)C(A8—N4—C(A7—C(B73.7 (3)
N3—C(A5—C(B5—C(B61.1 (3)C(A8—N4—C(A7—C(M3173.4 (2)
N3—C(A5—C(M2—C7174.8 (2)C(B1—C(A1—C(M4—C193.1 (3)
N3—C(A5—C(M2—C(A43.7 (4)C(B1—C(A1—C(M4—C(A8179.5 (2)
N3—C(A6—C(B6—C(B51.5 (3)C(B2—C(A2—C(M1—C15.7 (4)
N3—C(A6—C(M3—C13174.4 (2)C(B2—C(A2—C(M1—C(A3174.6 (2)
N3—C(A6—C(M3—C(A70.3 (4)C(B3—C(A3—C(M1—C12.6 (4)
N4—C(A7—C(B7—C(B81.6 (3)C(B3—C(A3—C(M1—C(A2177.1 (2)
N4—C(A7—C(M3—C13165.7 (2)C(B4—C(A4—C(M2—C70.9 (4)
N4—C(A7—C(M3—C(A69.0 (4)C(B4—C(A4—C(M2—C(A5177.6 (2)
N4—C(A8—C(B8—C(B73.5 (3)C(B5—C(A5—C(M2—C71.7 (4)
N4—C(A8—C(M4—C19166.2 (2)C(B5—C(A5—C(M2—C(A4179.8 (2)
N4—C(A8—C(M4—C(A110.3 (4)C(B6—C(A6—C(M3—C137.1 (4)
C1—C2—C3—C40.2 (4)C(B6—C(A6—C(M3—C(A7178.2 (2)
C2—C1—C6—C51.2 (4)C(B7—C(A7—C(M3—C1311.0 (4)
C2—C1—C(M1—C(A264.2 (3)C(B7—C(A7—C(M3—C(A6174.2 (2)
C2—C1—C(M1—C(A3115.5 (3)C(B8—C(A8—C(M4—C1910.0 (4)
C2—C3—C4—C50.8 (5)C(B8—C(A8—C(M4—C(A1173.5 (2)
C3—C4—C5—C60.4 (5)C(M1—C1—C2—C3178.2 (2)
C4—C5—C6—C10.6 (5)C(M1—C1—C6—C5177.8 (3)
C6—C1—C2—C30.8 (4)C(M1—C(A2—C(B2—C(B1180.0 (2)
C6—C1—C(M1—C(A2114.8 (3)C(M1—C(A3—C(B3—C(B4177.7 (2)
C6—C1—C(M1—C(A365.5 (3)C(M2—C7—C8—C9177.6 (2)
C7—C8—C9—C100.2 (4)C(M2—C7—C12—C11177.6 (2)
C8—C7—C12—C110.5 (4)C(M2—C(A4—C(B4—C(B3177.2 (2)
C8—C7—C(M2—C(A472.7 (3)C(M2—C(A5—C(B5—C(B6178.1 (2)
C8—C7—C(M2—C(A5105.9 (3)C(M3—C13—C14—C15178.7 (3)
C8—C9—C10—C110.1 (4)C(M3—C13—C18—C17179.6 (3)
C9—C10—C11—C120.2 (4)C(M3—C(A6—C(B6—C(B5177.3 (3)
C10—C11—C12—C70.1 (4)C(M3—C(A7—C(B7—C(B8175.6 (2)
C12—C7—C8—C90.5 (3)C(M4—C19—C20—C21176.7 (2)
C12—C7—C(M2—C(A4105.3 (3)C(M4—C19—C24—C23177.4 (2)
C12—C7—C(M2—C(A576.1 (3)C(M4—C(A1—C(B1—C(B2177.9 (2)
C13—C14—C15—C160.4 (6)C(M4—C(A8—C(B8—C(B7173.2 (2)
C14—C13—C18—C170.1 (4)C1Si—C1S—C2S—C3S178.4 (3)
C14—C13—C(M3—C(A6105.4 (3)C4S—C5S—C6S—C7S6 (3)
C14—C13—C(M3—C(A769.6 (3)C5S—C4S—C9S—C8S0.6 (15)
C14—C15—C16—C171.0 (5)C5S—C6S—C7S—C8S5 (3)
C15—C16—C17—C182.0 (5)C6S—C7S—C8S—C9S2 (3)
C16—C17—C18—C131.5 (5)C7S—C8S—C9S—C4S0.2 (19)
C18—C13—C14—C150.8 (5)C9S—C4S—C5S—C6S4 (3)
C18—C13—C(M3—C(A674.1 (3)
Symmetry code: (i) x+1/2, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4S—H4S···O30.952.383.177 (8)141
C10—H10···O2ii0.952.503.182 (3)129
C17—H17···O2iii0.952.533.350 (4)145
C22—H22···O2iv0.952.493.085 (3)120
Symmetry codes: (ii) x1/2, y+1, z+1/2; (iii) x, y+3/2, z+1/2; (iv) x+1/2, y+1, z+1/2.
Selected structural parameters (Å) for related metalloporphyrin nitrato complexes top
Δ4 is the displacement of the metal atom from the mean plane of the four pyrrole nitrogen atoms and Δ24 is the displacement of the metal atom from the 24-atom mean plane.
ComplexΔ4Δ24M—ON—O1M—NpRef.
[Mn(TPP)(NO3)] (Pccn) benzene and n-hexane hemisolvate0.230.222.1246 (18)1.260 (3) 1.236 (3) 1.230 (3)2.011 (6)This work
[Mn(TPP)(NO3)] (P1) benzene disolvate0.210.202.101 (3)1.298 (4) 1.226 (5) 1.226 (5)2.007 (9)(Suslick & Watson, 1991)
[Fe(OEP)(NO3)] (P21/c)0.400.451.966 (2)1.301 (3) 1.199 (3) 1.212 (3)2.047 (6)(Wyllie et al., 2007)
[Fe(OEP)(NO3)] (P1)0.460.502.016 (3)1.206 (5) 1.198 (4) 1.208 (6)2.056 (1)(Ellison et al., 1996)
[Fe(4-Me-TTP)(NO3)]0.470.531.971 (3)1.262 (5) 1.252 (5) 1.221 (4)2.063 (13)(Bhuyan & Sarkar, 2013)
[Fe(TPP)(NO3)]0.540.632.121 (6) 2.19 (10)1.27 (10) 1.285 (21) 1.217 (3)2.085 (10)(Wyllie et al., 2007)
[Fe(TpivPP)(NO3)]0.420.492.123 (3) 2.226 (3)1.271 (4) 1.252 (4) 1.214 (3)2.070 (16)(Munro & Scheidt, 1998)
[Fe(4-OMe-TPP)(NO3)]0.550.622.169 (5) 2.169 (5)1.216 (5) 1.276 (8) 1.216 (5)2.05 (3)(Bhuyan & Sarkar, 2013)
 

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