Crystal structure of bis­(1-ethyl-1H-imidazole-κN³)(5,10,15,20-tetra­phenyl­porphyrinato-κ⁴N)iron(II) tetra­hydro­furan monosolvate

The title iron(II)–porphyrin complex possesses inversion symmetry with the metal atom located on a center of symmetry. The iron(II) atom is coordinated in a symmetric octa­hedral geometry by four pyrrole N atoms of the porphyrin ligand in the equatorial plane and two N atoms of 1-ethyl­imidazole ligands in the axial sites. The dihedral angle between the 1-ethyl­imidazole plane and the plane of the closest Fe—N_p vector is 24.5(?)°.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in solvent or counterion
• R factor = 0.058
• wR factor = 0.167
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.28 Report
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         10 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          5 Note
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          1 Check
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.63A   From C29B            1.55 eA-3
PLAT977_ALERT_2_C Check Negative Difference Density on H30A             -0.39 eA-3

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          5 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         10 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT164_ALERT_4_G Nr. of Refined C-H H-Atoms in Heavy-Atom Struct.          2 Note
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          3 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT300_ALERT_4_G Atom Site Occupancy of O1B        Constrained at       0.15 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C28B       Constrained at       0.15 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C29B       Constrained at       0.15 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C30B       Constrained at       0.15 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C31B       Constrained at       0.15 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H28C       Constrained at       0.15 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H28D       Constrained at       0.15 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H29C       Constrained at       0.15 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H29D       Constrained at       0.15 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H30C       Constrained at       0.15 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H30D       Constrained at       0.15 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H31C       Constrained at       0.15 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H31D       Constrained at       0.15 Check
PLAT300_ALERT_4_G Atom Site Occupancy of O1A        Constrained at       0.35 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C28A       Constrained at       0.35 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C29A       Constrained at       0.35 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C30A       Constrained at       0.35 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C31A       Constrained at       0.35 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H28A       Constrained at       0.35 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H28B       Constrained at       0.35 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H29A       Constrained at       0.35 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H29B       Constrained at       0.35 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H30A       Constrained at       0.35 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H30B       Constrained at       0.35 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H31A       Constrained at       0.35 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H31B       Constrained at       0.35 Check
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  3  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd  2          3.90 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ...... Resd  3          4.55 Check
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O1A            109.1 Degree
PLAT794_ALERT_5_G Tentative Bond Valency for Fe1       (III)     .       3.70 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        113 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          6 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          5 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         14 Info

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 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
  34 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SHELXL2014 (Sheldrick, 2015b); data reduction: SAINT-Plus (Bruker, 2014) and XPREP (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: XP (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: XCIF (Sheldrick, 2008) and enCIFer (Allen et al., 2004).

Bis(1-ethyl-1H-imidazole-κN³)(5,10,15,20-tetraphenylporphyrinato-κ⁴N)iron(II) tetrahydrofuran monosolvate

Crystal data

[Fe(C44H28N4)(C5H8N2)2]·C4H8O	Z = 1
Mr = 932.92	F(000) = 490
Triclinic, P1	Dx = 1.235 Mg m^−3
a = 9.2962 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7051 (4) Å	Cell parameters from 9016 reflections
c = 13.4920 (5) Å	θ = 2.4–26.4°
α = 79.809 (1)°	µ = 0.35 mm^−1
β = 76.034 (1)°	T = 100 K
γ = 75.933 (1)°	Block, purple
V = 1253.90 (8) Å^3	0.26 × 0.17 × 0.08 mm

Data collection

Bruker D8 QUEST System diffractometer	4542 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
φ and ω scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −11→11
Tmin = 0.931, Tmax = 0.972	k = −13→13
19292 measured reflections	l = −16→16
5147 independent reflections

Refinement

Refinement on F^2	113 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.167	w = 1/[σ^2(Fo^2) + (0.0784P)^2 + 2.6414P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
5147 reflections	Δρmax = 1.53 e Å^−3
386 parameters	Δρmin = −0.46 e Å^−3

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	Occ. (<1)
Fe1	0.0000	0.5000	0.5000	0.00924 (16)
N3	0.1978 (2)	0.5561 (2)	0.45844 (17)	0.0121 (4)
N4	0.3804 (2)	0.6544 (2)	0.45874 (17)	0.0138 (5)
N1	0.0234 (2)	0.4581 (2)	0.35771 (16)	0.0118 (4)
N2	0.1056 (2)	0.3198 (2)	0.54207 (16)	0.0108 (4)
C1	−0.1057 (3)	0.6676 (3)	0.2771 (2)	0.0130 (5)
C2	−0.0246 (3)	0.5395 (3)	0.2750 (2)	0.0141 (5)
C3	0.0205 (3)	0.4727 (3)	0.1849 (2)	0.0205 (6)
H3	0.0037	0.5084	0.1180	0.025*
C4	0.0910 (3)	0.3506 (3)	0.2132 (2)	0.0196 (6)
H4	0.1318	0.2835	0.1704	0.024*
C5	0.0927 (3)	0.3410 (3)	0.3208 (2)	0.0137 (5)
C6	0.1548 (3)	0.2286 (2)	0.3780 (2)	0.0127 (5)
C7	0.1616 (3)	0.2208 (2)	0.4811 (2)	0.0120 (5)
C8	0.2351 (3)	0.1062 (3)	0.5377 (2)	0.0147 (5)
H8	0.2822	0.0254	0.5126	0.018*
C9	0.2248 (3)	0.1346 (3)	0.6327 (2)	0.0144 (5)
H9	0.2643	0.0783	0.6871	0.017*
C10	0.1421 (3)	0.2673 (2)	0.6363 (2)	0.0114 (5)
C11	0.2390 (3)	0.6380 (3)	0.5032 (2)	0.0152 (5)
H11	0.1767	0.6800	0.5598	0.018*
C12	0.3189 (3)	0.5190 (3)	0.3805 (2)	0.0168 (5)
H12	0.3230	0.4604	0.3340	0.020*
C13	0.4321 (3)	0.5794 (3)	0.3804 (2)	0.0183 (6)
H13	0.5283	0.5710	0.3346	0.022*
C14	0.4615 (3)	0.7433 (3)	0.4831 (2)	0.0193 (6)
H14A	0.454 (4)	0.818 (3)	0.431 (3)	0.021 (8)*
H14B	0.570 (4)	0.701 (3)	0.468 (3)	0.024 (9)*
C15	0.4039 (3)	0.7774 (3)	0.5914 (2)	0.0204 (6)
H15A	0.2967	0.8210	0.6004	0.031*
H15B	0.4627	0.8354	0.6041	0.031*
H15C	0.4148	0.6980	0.6403	0.031*
C16	−0.1574 (3)	0.7373 (3)	0.1816 (2)	0.0153 (5)
C17	−0.1145 (4)	0.8526 (3)	0.1325 (2)	0.0235 (6)
H17	−0.0500	0.8880	0.1596	0.028*
C18	−0.1651 (4)	0.9162 (3)	0.0440 (2)	0.0304 (7)
H18	−0.1365	0.9956	0.0122	0.037*
C19	−0.2562 (4)	0.8655 (3)	0.0023 (2)	0.0307 (8)
H19	−0.2888	0.9087	−0.0588	0.037*
C20	−0.2998 (4)	0.7512 (3)	0.0498 (2)	0.0265 (7)
H20	−0.3630	0.7159	0.0214	0.032*
C21	−0.2516 (3)	0.6879 (3)	0.1388 (2)	0.0194 (6)
H21	−0.2830	0.6098	0.1711	0.023*
C22	0.2182 (3)	0.1072 (3)	0.3273 (2)	0.0138 (5)
C23	0.3640 (3)	0.0857 (3)	0.2667 (2)	0.0156 (5)
H23	0.4234	0.1495	0.2557	0.019*
C24	0.4230 (3)	−0.0285 (3)	0.2222 (2)	0.0195 (6)
H24	0.5230	−0.0426	0.1815	0.023*
C25	0.3368 (3)	−0.1223 (3)	0.2370 (2)	0.0210 (6)
H25	0.3771	−0.1998	0.2059	0.025*
C26	0.1915 (4)	−0.1018 (3)	0.2975 (2)	0.0230 (6)
H26	0.1324	−0.1659	0.3084	0.028*
C27	0.1325 (3)	0.0123 (3)	0.3422 (2)	0.0201 (6)
H27	0.0329	0.0259	0.3834	0.024*
O1A	0.6922 (6)	0.1716 (5)	0.1646 (4)	0.0128 (6)	0.35
C29A	0.8416 (9)	0.3157 (7)	0.0625 (5)	0.0124 (7)	0.35
H29A	0.9472	0.3111	0.0233	0.015*	0.35
H29B	0.8013	0.4026	0.0856	0.015*	0.35
C28A	0.8331 (9)	0.2105 (7)	0.1517 (5)	0.0127 (7)	0.35
H28A	0.9189	0.1358	0.1379	0.015*	0.35
H28B	0.8380	0.2429	0.2148	0.015*	0.35
C30A	0.7387 (8)	0.2857 (7)	−0.0043 (5)	0.0122 (7)	0.35
H30A	0.6901	0.3657	−0.0431	0.015*	0.35
H30B	0.7972	0.2230	−0.0528	0.015*	0.35
C31A	0.6257 (9)	0.2286 (7)	0.0775 (5)	0.0128 (7)	0.35
H31A	0.5353	0.2970	0.0981	0.015*	0.35
H31B	0.5932	0.1616	0.0511	0.015*	0.35
O1B	0.5583 (12)	0.4284 (11)	−0.0007 (7)	0.0124 (7)	0.15
C28B	0.5266 (16)	0.4209 (16)	0.1079 (8)	0.0118 (8)	0.15
H28C	0.4395	0.3790	0.1392	0.014*	0.15
H28D	0.5040	0.5083	0.1299	0.014*	0.15
C29B	0.6701 (15)	0.3396 (16)	0.1373 (10)	0.0126 (6)	0.15
H29C	0.6608	0.2484	0.1609	0.015*	0.15
H29D	0.6966	0.3747	0.1921	0.015*	0.15
C30B	0.7903 (17)	0.3508 (18)	0.0340 (10)	0.0125 (7)	0.15
H30C	0.8286	0.4317	0.0238	0.015*	0.15
H30D	0.8767	0.2754	0.0320	0.015*	0.15
C31B	0.6999 (14)	0.3523 (16)	−0.0446 (11)	0.0125 (7)	0.15
H31C	0.7441	0.3940	−0.1130	0.015*	0.15
H31D	0.6909	0.2638	−0.0506	0.015*	0.15

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0091 (3)	0.0097 (3)	0.0089 (3)	−0.00137 (18)	−0.00237 (19)	−0.00117 (18)
N3	0.0125 (11)	0.0108 (10)	0.0129 (10)	−0.0014 (8)	−0.0040 (8)	−0.0004 (8)
N4	0.0117 (10)	0.0141 (11)	0.0160 (11)	−0.0036 (8)	−0.0033 (9)	−0.0013 (9)
N1	0.0110 (10)	0.0118 (10)	0.0120 (10)	−0.0012 (8)	−0.0024 (8)	−0.0013 (8)
N2	0.0109 (10)	0.0112 (10)	0.0107 (10)	−0.0032 (8)	−0.0024 (8)	−0.0011 (8)
C1	0.0125 (12)	0.0152 (12)	0.0113 (12)	−0.0038 (10)	−0.0036 (10)	0.0006 (10)
C2	0.0138 (12)	0.0172 (13)	0.0111 (12)	−0.0024 (10)	−0.0029 (10)	−0.0021 (10)
C3	0.0249 (15)	0.0221 (14)	0.0118 (13)	0.0036 (11)	−0.0059 (11)	−0.0041 (11)
C4	0.0225 (14)	0.0213 (14)	0.0126 (13)	0.0034 (11)	−0.0040 (11)	−0.0061 (11)
C5	0.0117 (12)	0.0162 (13)	0.0130 (12)	−0.0015 (10)	−0.0020 (10)	−0.0043 (10)
C6	0.0111 (12)	0.0122 (12)	0.0152 (12)	−0.0017 (9)	−0.0020 (10)	−0.0041 (10)
C7	0.0101 (12)	0.0105 (12)	0.0156 (12)	−0.0031 (9)	−0.0022 (10)	−0.0018 (10)
C8	0.0168 (13)	0.0104 (12)	0.0176 (13)	−0.0032 (10)	−0.0052 (10)	−0.0014 (10)
C9	0.0167 (13)	0.0115 (12)	0.0158 (13)	−0.0037 (10)	−0.0061 (10)	0.0009 (10)
C10	0.0106 (12)	0.0115 (12)	0.0129 (12)	−0.0039 (9)	−0.0040 (9)	0.0003 (9)
C11	0.0138 (12)	0.0177 (13)	0.0150 (12)	−0.0043 (10)	−0.0031 (10)	−0.0031 (10)
C12	0.0148 (13)	0.0157 (13)	0.0183 (13)	−0.0028 (10)	0.0000 (11)	−0.0038 (10)
C13	0.0141 (13)	0.0183 (13)	0.0207 (14)	−0.0034 (10)	0.0011 (11)	−0.0043 (11)
C14	0.0171 (14)	0.0199 (14)	0.0242 (15)	−0.0095 (11)	−0.0066 (11)	−0.0003 (12)
C15	0.0233 (15)	0.0176 (13)	0.0236 (15)	−0.0058 (11)	−0.0102 (12)	−0.0018 (11)
C16	0.0144 (13)	0.0176 (13)	0.0110 (12)	0.0020 (10)	−0.0027 (10)	−0.0012 (10)
C17	0.0253 (15)	0.0252 (15)	0.0183 (14)	−0.0060 (12)	−0.0050 (12)	0.0027 (12)
C18	0.0369 (18)	0.0284 (17)	0.0189 (15)	−0.0022 (14)	−0.0047 (13)	0.0075 (12)
C19	0.0352 (18)	0.0357 (18)	0.0130 (14)	0.0101 (14)	−0.0093 (13)	0.0001 (12)
C20	0.0250 (16)	0.0354 (18)	0.0175 (14)	0.0070 (13)	−0.0088 (12)	−0.0117 (13)
C21	0.0199 (14)	0.0203 (14)	0.0162 (13)	0.0026 (11)	−0.0042 (11)	−0.0066 (11)
C22	0.0162 (13)	0.0135 (12)	0.0126 (12)	−0.0002 (10)	−0.0070 (10)	−0.0022 (10)
C23	0.0158 (13)	0.0179 (13)	0.0144 (13)	−0.0022 (10)	−0.0049 (10)	−0.0046 (10)
C24	0.0199 (14)	0.0220 (14)	0.0145 (13)	0.0048 (11)	−0.0053 (11)	−0.0073 (11)
C25	0.0300 (16)	0.0152 (13)	0.0182 (14)	0.0046 (11)	−0.0121 (12)	−0.0064 (11)
C26	0.0298 (16)	0.0153 (14)	0.0279 (16)	−0.0061 (12)	−0.0111 (13)	−0.0038 (12)
C27	0.0175 (14)	0.0193 (14)	0.0242 (14)	−0.0042 (11)	−0.0048 (11)	−0.0038 (11)
O1A	0.0166 (15)	0.0189 (15)	0.0051 (13)	−0.0094 (12)	−0.0044 (12)	0.0030 (11)
C29A	0.0171 (15)	0.0180 (15)	0.0047 (13)	−0.0091 (12)	−0.0046 (12)	0.0024 (12)
C28A	0.0169 (15)	0.0187 (15)	0.0049 (14)	−0.0093 (12)	−0.0043 (12)	0.0028 (12)
C30A	0.0174 (15)	0.0176 (15)	0.0042 (13)	−0.0090 (12)	−0.0048 (12)	0.0025 (12)
C31A	0.0170 (15)	0.0185 (15)	0.0050 (13)	−0.0088 (12)	−0.0045 (12)	0.0030 (12)
O1B	0.0180 (16)	0.0178 (16)	0.0042 (14)	−0.0089 (13)	−0.0050 (13)	0.0023 (13)
C28B	0.0168 (16)	0.0179 (16)	0.0039 (15)	−0.0093 (14)	−0.0051 (13)	0.0024 (13)
C29B	0.0170 (15)	0.0185 (15)	0.0048 (13)	−0.0092 (12)	−0.0047 (12)	0.0030 (11)
C30B	0.0174 (15)	0.0181 (15)	0.0045 (14)	−0.0090 (13)	−0.0046 (12)	0.0025 (12)
C31B	0.0177 (16)	0.0182 (16)	0.0044 (15)	−0.0090 (13)	−0.0048 (13)	0.0022 (13)

Geometric parameters (Å, º)

Fe1—N2	1.992 (2)	C18—C19	1.375 (5)
Fe1—N2^i	1.992 (2)	C18—H18	0.9500
Fe1—N3	1.994 (2)	C19—C20	1.382 (5)
Fe1—N3^i	1.994 (2)	C19—H19	0.9500
Fe1—N1^i	1.998 (2)	C20—C21	1.388 (4)
Fe1—N1	1.998 (2)	C20—H20	0.9500
N3—C11	1.320 (3)	C21—H21	0.9500
N3—C12	1.375 (3)	C22—C23	1.392 (4)
N4—C11	1.346 (3)	C22—C27	1.396 (4)
N4—C13	1.364 (4)	C23—C24	1.389 (4)
N4—C14	1.471 (3)	C23—H23	0.9500
N1—C5	1.381 (3)	C24—C25	1.390 (4)
N1—C2	1.383 (3)	C24—H24	0.9500
N2—C7	1.379 (3)	C25—C26	1.388 (4)
N2—C10	1.382 (3)	C25—H25	0.9500
C1—C10^i	1.396 (4)	C26—C27	1.390 (4)
C1—C2	1.397 (4)	C26—H26	0.9500
C1—C16	1.494 (3)	C27—H27	0.9500
C2—C3	1.442 (4)	O1A—C28A	1.431 (9)
C3—C4	1.346 (4)	O1A—C31A	1.432 (8)
C3—H3	0.9500	C29A—C28A	1.497 (10)
C4—C5	1.440 (4)	C29A—C30A	1.580 (10)
C4—H4	0.9500	C29A—H29A	0.9900
C5—C6	1.388 (4)	C29A—H29B	0.9900
C6—C7	1.395 (4)	C28A—H28A	0.9900
C6—C22	1.502 (3)	C28A—H28B	0.9900
C7—C8	1.438 (4)	C30A—C31A	1.486 (10)
C8—C9	1.346 (4)	C30A—H30A	0.9900
C8—H8	0.9500	C30A—H30B	0.9900
C9—C10	1.444 (4)	C31A—H31A	0.9900
C9—H9	0.9500	C31A—H31B	0.9900
C10—C1^i	1.396 (4)	O1B—C28B	1.415 (9)
C11—H11	0.9500	O1B—C31B	1.421 (9)
C12—C13	1.363 (4)	O1B—O1B^ii	1.65 (2)
C12—H12	0.9500	C28B—C29B	1.505 (10)
C13—H13	0.9500	C28B—H28C	0.9900
C14—C15	1.507 (4)	C28B—H28D	0.9900
C14—H14A	0.97 (4)	C29B—C30B	1.568 (9)
C14—H14B	0.99 (4)	C29B—H29C	0.9900
C15—H15A	0.9800	C29B—H29D	0.9900
C15—H15B	0.9800	C30B—C31B	1.499 (9)
C15—H15C	0.9800	C30B—H30C	0.9900
C16—C17	1.394 (4)	C30B—H30D	0.9900
C16—C21	1.398 (4)	C31B—H31C	0.9900
C17—C18	1.392 (4)	C31B—H31D	0.9900
C17—H17	0.9500
N2—Fe1—N2^i	180.0	C16—C17—H17	119.7
N2—Fe1—N3	90.27 (9)	C19—C18—C17	120.7 (3)
N2^i—Fe1—N3	89.72 (9)	C19—C18—H18	119.6
N2—Fe1—N3^i	89.73 (9)	C17—C18—H18	119.6
N2^i—Fe1—N3^i	90.28 (9)	C18—C19—C20	119.5 (3)
N3—Fe1—N3^i	180.0	C18—C19—H19	120.3
N2—Fe1—N1^i	89.51 (9)	C20—C19—H19	120.3
N2^i—Fe1—N1^i	90.49 (9)	C19—C20—C21	120.2 (3)
N3—Fe1—N1^i	89.95 (9)	C19—C20—H20	119.9
N3^i—Fe1—N1^i	90.05 (9)	C21—C20—H20	119.9
N2—Fe1—N1	90.49 (9)	C20—C21—C16	121.0 (3)
N2^i—Fe1—N1	89.51 (9)	C20—C21—H21	119.5
N3—Fe1—N1	90.05 (9)	C16—C21—H21	119.5
N3^i—Fe1—N1	89.95 (9)	C23—C22—C27	118.9 (2)
N1^i—Fe1—N1	180.0	C23—C22—C6	120.9 (2)
C11—N3—C12	105.6 (2)	C27—C22—C6	120.2 (2)
C11—N3—Fe1	125.62 (19)	C24—C23—C22	120.4 (3)
C12—N3—Fe1	128.74 (18)	C24—C23—H23	119.8
C11—N4—C13	107.0 (2)	C22—C23—H23	119.8
C11—N4—C14	127.4 (2)	C23—C24—C25	120.4 (3)
C13—N4—C14	125.5 (2)	C23—C24—H24	119.8
C5—N1—C2	105.2 (2)	C25—C24—H24	119.8
C5—N1—Fe1	127.09 (17)	C26—C25—C24	119.6 (3)
C2—N1—Fe1	127.71 (18)	C26—C25—H25	120.2
C7—N2—C10	105.1 (2)	C24—C25—H25	120.2
C7—N2—Fe1	126.70 (17)	C25—C26—C27	120.0 (3)
C10—N2—Fe1	128.22 (17)	C25—C26—H26	120.0
C10^i—C1—C2	123.5 (2)	C27—C26—H26	120.0
C10^i—C1—C16	118.7 (2)	C26—C27—C22	120.7 (3)
C2—C1—C16	117.8 (2)	C26—C27—H27	119.7
N1—C2—C1	125.7 (2)	C22—C27—H27	119.7
N1—C2—C3	110.1 (2)	C28A—O1A—C31A	109.1 (5)
C1—C2—C3	124.3 (2)	C28A—C29A—C30A	102.9 (6)
C4—C3—C2	107.3 (2)	C28A—C29A—H29A	111.2
C4—C3—H3	126.3	C30A—C29A—H29A	111.2
C2—C3—H3	126.3	C28A—C29A—H29B	111.2
C3—C4—C5	107.0 (2)	C30A—C29A—H29B	111.2
C3—C4—H4	126.5	H29A—C29A—H29B	109.1
C5—C4—H4	126.5	O1A—C28A—C29A	107.4 (6)
N1—C5—C6	125.6 (2)	O1A—C28A—H28A	110.2
N1—C5—C4	110.4 (2)	C29A—C28A—H28A	110.2
C6—C5—C4	124.0 (2)	O1A—C28A—H28B	110.2
C5—C6—C7	123.9 (2)	C29A—C28A—H28B	110.2
C5—C6—C22	118.7 (2)	H28A—C28A—H28B	108.5
C7—C6—C22	117.3 (2)	C31A—C30A—C29A	100.8 (5)
N2—C7—C6	126.2 (2)	C31A—C30A—H30A	111.6
N2—C7—C8	110.5 (2)	C29A—C30A—H30A	111.6
C6—C7—C8	123.3 (2)	C31A—C30A—H30B	111.6
C9—C8—C7	107.3 (2)	C29A—C30A—H30B	111.6
C9—C8—H8	126.4	H30A—C30A—H30B	109.4
C7—C8—H8	126.4	O1A—C31A—C30A	109.3 (6)
C8—C9—C10	106.9 (2)	O1A—C31A—H31A	109.8
C8—C9—H9	126.6	C30A—C31A—H31A	109.8
C10—C9—H9	126.6	O1A—C31A—H31B	109.8
N2—C10—C1^i	125.3 (2)	C30A—C31A—H31B	109.8
N2—C10—C9	110.3 (2)	H31A—C31A—H31B	108.3
C1^i—C10—C9	124.3 (2)	C28B—O1B—C31B	115.1 (11)
N3—C11—N4	111.6 (2)	C28B—O1B—O1B^ii	86.3 (9)
N3—C11—H11	124.2	C31B—O1B—O1B^ii	147.8 (13)
N4—C11—H11	124.2	O1B—C28B—C29B	103.8 (11)
C13—C12—N3	109.2 (2)	O1B—C28B—H28C	111.0
C13—C12—H12	125.4	C29B—C28B—H28C	111.0
N3—C12—H12	125.4	O1B—C28B—H28D	111.0
C12—C13—N4	106.6 (2)	C29B—C28B—H28D	111.0
C12—C13—H13	126.7	H28C—C28B—H28D	109.0
N4—C13—H13	126.7	C28B—C29B—C30B	102.7 (11)
N4—C14—C15	112.8 (2)	C28B—C29B—H29C	111.2
N4—C14—H14A	106 (2)	C30B—C29B—H29C	111.2
C15—C14—H14A	113 (2)	C28B—C29B—H29D	111.2
N4—C14—H14B	106 (2)	C30B—C29B—H29D	111.2
C15—C14—H14B	114 (2)	H29C—C29B—H29D	109.1
H14A—C14—H14B	104 (3)	C31B—C30B—C29B	102.1 (11)
C14—C15—H15A	109.5	C31B—C30B—H30C	111.4
C14—C15—H15B	109.5	C29B—C30B—H30C	111.4
H15A—C15—H15B	109.5	C31B—C30B—H30D	111.4
C14—C15—H15C	109.5	C29B—C30B—H30D	111.4
H15A—C15—H15C	109.5	H30C—C30B—H30D	109.2
H15B—C15—H15C	109.5	O1B—C31B—C30B	100.4 (11)
C17—C16—C21	117.9 (3)	O1B—C31B—H31C	111.7
C17—C16—C1	121.7 (3)	C30B—C31B—H31C	111.7
C21—C16—C1	120.4 (2)	O1B—C31B—H31D	111.7
C18—C17—C16	120.6 (3)	C30B—C31B—H31D	111.7
C18—C17—H17	119.7	H31C—C31B—H31D	109.5
C5—N1—C2—C1	177.7 (3)	Fe1—N3—C12—C13	−178.97 (19)
Fe1—N1—C2—C1	−2.8 (4)	N3—C12—C13—N4	−0.1 (3)
C5—N1—C2—C3	−2.0 (3)	C11—N4—C13—C12	−0.3 (3)
Fe1—N1—C2—C3	177.45 (19)	C14—N4—C13—C12	−176.0 (2)
C10^i—C1—C2—N1	3.6 (4)	C11—N4—C14—C15	24.6 (4)
C16—C1—C2—N1	−175.7 (2)	C13—N4—C14—C15	−160.6 (3)
C10^i—C1—C2—C3	−176.7 (3)	C10^i—C1—C16—C17	59.0 (4)
C16—C1—C2—C3	4.0 (4)	C2—C1—C16—C17	−121.7 (3)
N1—C2—C3—C4	2.0 (3)	C10^i—C1—C16—C21	−120.9 (3)
C1—C2—C3—C4	−177.8 (3)	C2—C1—C16—C21	58.4 (4)
C2—C3—C4—C5	−1.0 (3)	C21—C16—C17—C18	0.4 (4)
C2—N1—C5—C6	−178.1 (3)	C1—C16—C17—C18	−179.5 (3)
Fe1—N1—C5—C6	2.4 (4)	C16—C17—C18—C19	−1.2 (5)
C2—N1—C5—C4	1.4 (3)	C17—C18—C19—C20	1.1 (5)
Fe1—N1—C5—C4	−178.10 (18)	C18—C19—C20—C21	−0.2 (5)
C3—C4—C5—N1	−0.2 (3)	C19—C20—C21—C16	−0.6 (4)
C3—C4—C5—C6	179.3 (3)	C17—C16—C21—C20	0.5 (4)
N1—C5—C6—C7	−3.2 (4)	C1—C16—C21—C20	−179.6 (3)
C4—C5—C6—C7	177.4 (3)	C5—C6—C22—C23	82.2 (3)
N1—C5—C6—C22	176.5 (2)	C7—C6—C22—C23	−98.0 (3)
C4—C5—C6—C22	−2.8 (4)	C5—C6—C22—C27	−99.3 (3)
C10—N2—C7—C6	−178.6 (2)	C7—C6—C22—C27	80.5 (3)
Fe1—N2—C7—C6	0.0 (4)	C27—C22—C23—C24	−0.2 (4)
C10—N2—C7—C8	−0.7 (3)	C6—C22—C23—C24	178.3 (2)
Fe1—N2—C7—C8	177.96 (17)	C22—C23—C24—C25	0.5 (4)
C5—C6—C7—N2	1.9 (4)	C23—C24—C25—C26	−0.7 (4)
C22—C6—C7—N2	−177.8 (2)	C24—C25—C26—C27	0.5 (4)
C5—C6—C7—C8	−175.8 (2)	C25—C26—C27—C22	−0.2 (4)
C22—C6—C7—C8	4.5 (4)	C23—C22—C27—C26	0.0 (4)
N2—C7—C8—C9	−0.2 (3)	C6—C22—C27—C26	−178.5 (3)
C6—C7—C8—C9	177.8 (2)	C31A—O1A—C28A—C29A	10.8 (8)
C7—C8—C9—C10	0.9 (3)	C30A—C29A—C28A—O1A	−26.6 (8)
C7—N2—C10—C1^i	−179.2 (2)	C28A—C29A—C30A—C31A	31.6 (7)
Fe1—N2—C10—C1^i	2.3 (4)	C28A—O1A—C31A—C30A	11.1 (8)
C7—N2—C10—C9	1.2 (3)	C29A—C30A—C31A—O1A	−26.5 (8)
Fe1—N2—C10—C9	−177.34 (17)	C31B—O1B—C28B—C29B	5.3 (17)
C8—C9—C10—N2	−1.4 (3)	O1B^ii—O1B—C28B—C29B	−149.7 (13)
C8—C9—C10—C1^i	179.0 (2)	O1B—C28B—C29B—C30B	19.5 (16)
C12—N3—C11—N4	−0.5 (3)	C28B—C29B—C30B—C31B	−36.3 (16)
Fe1—N3—C11—N4	178.81 (17)	C28B—O1B—C31B—C30B	−28.6 (17)
C13—N4—C11—N3	0.5 (3)	O1B^ii—O1B—C31B—C30B	99 (2)
C14—N4—C11—N3	176.1 (2)	C29B—C30B—C31B—O1B	38.1 (16)
C11—N3—C12—C13	0.4 (3)

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

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the N2/C7–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···Cg^iii	0.99 (4)	2.69 (4)	3.437 (3)	133 (2)

Symmetry code: (iii) −x+1, −y+1, −z+1.