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The chemistry of transition-metal com­plexes with unusually high coordination numbers has been of inter­est because of their application in catalytic and biological systems. Deprotonation of the ionogenic tetra­dentate ligand 6,6′-bis­(1H-tetra­zol-5-yl)-2,2′-bi­pyridine [H2bipy(ttr)2] in the presence of iron(III) and tetra-n-butyl­ammonium bromide, [n-Bu4N]Br, in solution resulted in the synthesis of a rare octa­coordinated anionic mononuclear com­plex, tetra-n-butyl­ammonium bis­[6,6′-bis­(tetra­zol-1-id-5-yl)-2,2′-bi­pyridine]­iron(III) methanol hemisolvate dihydrate, (C16H36N)[Fe(C12H6N10)2]·0.5CH3OH·2H2O or [n-Bu4N][Fe{bipy(ttr)2}2]·0.5CH3OH·2H2O (1), which has been structurally characterized by elemental analysis, powder X-ray diffraction (PXRD) and single-crystal X-ray diffraction. In 1, the coordination sphere of the iron(III) ion is a distorted bis-disphenoid dodeca­hedron, in which the eight coordination positions are occupied by eight N atoms from two independent tetra­dentate [bipy(ttr)2]2− anionic ligands, therefore forming the anionic [Fe{bipy(ttr)2}2] unit, with the negative charge balanced by a free [n-Bu4N]+ cation. An investigation of the mag­netic properties of 1 revealed a gradual incom­plete spin-crossover behaviour below 150 K.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620010451/lf3118sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620010451/lf3118Isup2.hkl
Contains datablock I

CCDC reference: 2000679

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b).

Tetra-n-butylammonium bis[6,6'-bis(tetrazol-1-id-5-yl)-2,2'-bipyridine]iron(III) methanol hemisolvate dihydrate top
Crystal data top
(C16H36N)[Fe(C12H6N10)2]·0.5CH4O·2H2OZ = 2
Mr = 930.80F(000) = 980
Triclinic, P1Dx = 1.297 Mg m3
a = 12.5006 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.7609 (10) ÅCell parameters from 4871 reflections
c = 15.0775 (16) Åθ = 3.0–29.0°
α = 84.538 (8)°µ = 0.38 mm1
β = 86.265 (7)°T = 293 K
γ = 85.919 (7)°Block, dark-brown
V = 2384.0 (4) Å30.23 × 0.19 × 0.11 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
6081 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
φ and ω scansθmax = 25.0°, θmin = 3.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 1314
Tmin = 0.613, Tmax = 1.000k = 1115
15117 measured reflectionsl = 1717
8320 independent reflections
Refinement top
Refinement on F27 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.069H-atom parameters constrained
wR(F2) = 0.191 w = 1/[σ2(Fo2) + (0.0894P)2 + 2.2058P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
8320 reflectionsΔρmax = 0.91 e Å3
600 parametersΔρmin = 0.56 e Å3
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.

Refinement. Single crystal of complex 1with suitable dimensions for X-ray diffraction analyses was mounted on a glass rod, and the crystal data was collected on a Bruker APEX2 CCD diffractometer with a Mo Kα sealed tube (λ = 0.71073 Å) at room temperature, using the ω scan mode. The structure was solved by the direct method and expanded employing Fourier difference technique with the SHELXTL-2018/3 program package (Sheldrick, 2015). All the non-hydrogen atoms were refined anisotropically with anisotropic displacement coefficients.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Fe10.40486 (4)0.73515 (4)0.23744 (3)0.02966 (18)
O10.8768 (3)0.4745 (3)0.0921 (2)0.0743 (11)
H1O10.8566720.5344940.1098290.089*
H2O10.8652520.4769140.0369990.089*
O20.0744 (3)0.3622 (3)0.1204 (3)0.0793 (12)
H1O20.1259500.4027550.1145400.095*
H2O20.0161100.4007550.1178200.095*
O30.0494 (6)0.1942 (5)1.0249 (6)0.069 (2)0.5
H30.0022210.1932921.0652570.104*0.5
N10.5134 (2)0.7571 (3)0.10729 (19)0.0329 (7)
N20.5527 (2)0.6399 (3)0.2523 (2)0.0337 (7)
N30.3269 (3)0.8512 (3)0.1293 (2)0.0360 (8)
N40.2505 (3)0.7926 (3)0.2896 (2)0.0397 (8)
N50.1951 (3)0.7784 (3)0.3689 (2)0.0523 (10)
N60.1041 (3)0.8345 (4)0.3639 (3)0.0638 (12)
N70.0974 (3)0.8884 (4)0.2818 (3)0.0594 (11)
N80.5927 (3)0.5737 (3)0.3195 (2)0.0393 (8)
N90.6874 (3)0.5359 (3)0.2934 (2)0.0450 (9)
N100.7130 (3)0.5754 (3)0.2088 (2)0.0409 (8)
N110.4779 (2)0.8796 (3)0.25647 (19)0.0336 (7)
N120.5086 (3)0.9617 (3)0.2005 (2)0.0442 (9)
N130.5487 (3)1.0287 (3)0.2482 (2)0.0473 (9)
N140.5456 (3)0.9920 (3)0.3353 (2)0.0416 (8)
N150.4346 (2)0.7405 (3)0.38862 (19)0.0315 (7)
N160.3474 (2)0.5879 (3)0.32724 (19)0.0314 (7)
N170.3387 (3)0.6284 (3)0.1558 (2)0.0384 (8)
N180.3214 (3)0.6341 (3)0.0680 (2)0.0493 (10)
N190.2693 (3)0.5515 (3)0.0551 (2)0.0551 (10)
N200.2521 (3)0.4907 (3)0.1324 (2)0.0473 (9)
N210.8869 (3)0.1925 (3)0.3105 (2)0.0493 (9)
C10.3007 (3)0.5146 (3)0.2876 (3)0.0355 (9)
C20.4795 (3)0.8240 (3)0.4127 (2)0.0339 (9)
C30.6095 (3)0.7033 (3)0.1033 (2)0.0341 (9)
C40.2282 (3)0.8954 (3)0.1489 (3)0.0409 (10)
C50.6285 (3)0.6380 (3)0.1865 (2)0.0340 (9)
C60.3760 (3)0.8756 (3)0.0495 (3)0.0383 (10)
C70.5021 (3)0.8340 (4)0.5006 (3)0.0440 (10)
H70.5319610.8938570.5162820.053*
C80.6796 (3)0.7114 (4)0.0285 (3)0.0473 (11)
H80.7457230.6730650.0269030.057*
C90.5021 (3)0.9011 (3)0.3374 (2)0.0345 (9)
C100.2955 (3)0.5406 (3)0.1920 (3)0.0382 (9)
C110.3584 (3)0.5744 (3)0.4150 (3)0.0362 (9)
C120.4323 (3)0.6655 (4)0.5393 (3)0.0433 (10)
H120.4165320.6101150.5817280.052*
C130.4092 (3)0.6617 (3)0.4504 (2)0.0350 (9)
C140.4830 (3)0.8221 (3)0.0366 (2)0.0360 (9)
C150.5492 (4)0.8341 (4)0.0396 (3)0.0454 (11)
H150.5276490.8793760.0880880.054*
C160.1885 (3)0.8607 (4)0.2387 (3)0.0437 (10)
C170.3233 (4)0.4866 (4)0.4666 (3)0.0468 (11)
H170.3323270.4780600.5277000.056*
C180.2635 (4)0.4250 (4)0.3354 (3)0.0535 (12)
H180.2314360.3748500.3070480.064*
C190.3276 (4)0.9450 (4)0.0144 (3)0.0496 (11)
H190.3620730.9605170.0702000.059*
C200.6479 (4)0.7786 (4)0.0436 (3)0.0531 (12)
H200.6931690.7864530.0948830.064*
C210.4786 (4)0.7522 (4)0.5634 (3)0.0520 (12)
H210.4940800.7556120.6225410.062*
C220.1766 (4)0.9661 (4)0.0882 (3)0.0563 (12)
H220.1086390.9966710.1024810.068*
C230.2750 (4)0.4122 (4)0.4258 (3)0.0573 (13)
H230.2500680.3530550.4594820.069*
C240.2277 (4)0.9903 (4)0.0064 (3)0.0628 (14)
H240.1942091.0378590.0352870.075*
C250.8226 (3)0.2276 (4)0.2296 (3)0.0484 (11)
H25A0.8565010.2866390.1965540.058*
H25B0.8275240.1703700.1912340.058*
C260.7063 (3)0.2597 (4)0.2475 (3)0.0476 (11)
H26A0.6998640.3142710.2884740.057*
H26B0.6699170.1995710.2757920.057*
C270.8841 (4)0.2799 (5)0.3723 (3)0.0595 (13)
H27A0.9243590.2546130.4238360.071*
H27B0.8101910.2952440.3934810.071*
C281.0010 (3)0.1668 (4)0.2753 (3)0.0555 (12)
H28A1.0001860.1076410.2394790.067*
H28B1.0233090.2266580.2357080.067*
C290.6520 (4)0.3006 (5)0.1628 (3)0.0607 (14)
H29A0.6947040.3539940.1305610.073*
H29B0.6508550.2430040.1253250.073*
C300.8424 (4)0.0966 (5)0.3640 (4)0.0675 (16)
H30A0.8887450.0752970.4125820.081*
H30B0.7722590.1176920.3903730.081*
C310.9293 (4)0.3816 (4)0.3303 (4)0.0651 (14)
H31A0.9988030.3649770.3006430.078*
H31B0.8820630.4133350.2851490.078*
C320.5394 (4)0.3469 (5)0.1776 (4)0.0754 (17)
H32A0.4951770.2936000.2063120.113*
H32B0.5115550.3728710.1212710.113*
H32C0.5393240.4039310.2148370.113*
C330.9420 (5)0.4607 (6)0.3962 (5)0.096 (2)
H33A0.9931190.4310500.4389710.115*
H33B0.8735650.4741740.4285920.115*
C340.9801 (7)0.5638 (6)0.3520 (6)0.119 (3)
H34A1.0501940.5517400.3232910.179*
H34B0.9835730.6126430.3962110.179*
H34C0.9308990.5926040.3083100.179*
C351.1950 (4)0.1345 (5)0.2937 (5)0.085 (2)
H35A1.1958150.0844020.2490300.102*
H35B1.2079350.2029990.2627640.102*
C361.0844 (4)0.1404 (5)0.3415 (4)0.0703 (15)
H36A1.0714730.0731500.3748310.084*
H36B1.0806730.1939050.3833990.084*
C370.8311 (4)0.0024 (4)0.3141 (4)0.0731 (16)
H37A0.8984540.0141930.2810620.088*
H37B0.7763270.0193010.2713630.088*
C380.8012 (5)0.0935 (6)0.3755 (5)0.098 (2)
H38A0.8585720.1132270.4154480.118*
H38B0.7368470.0750910.4117300.118*
C391.2833 (5)0.1027 (8)0.3534 (6)0.130 (3)
H39A1.2862770.1543100.3953620.196*
H39B1.3502600.0977290.3185790.196*
H39C1.2706990.0353520.3850300.196*
C400.7817 (7)0.1871 (6)0.3260 (8)0.142 (4)
H40A0.7292780.1666000.2827270.213*
H40B0.7556560.2426630.3674970.213*
H40C0.8476610.2116510.2962020.213*
C410.0065 (15)0.2379 (14)0.9386 (11)0.168 (8)0.5
H41A0.0692710.2291700.9402300.251*0.5
H41B0.0420520.2012930.8910820.251*0.5
H41C0.0189190.3116100.9285960.251*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0352 (3)0.0246 (3)0.0297 (3)0.0012 (2)0.0034 (2)0.0045 (2)
O10.067 (2)0.090 (3)0.069 (2)0.010 (2)0.0059 (18)0.030 (2)
O20.067 (2)0.060 (3)0.111 (3)0.0179 (19)0.002 (2)0.007 (2)
O30.073 (4)0.020 (3)0.113 (6)0.024 (3)0.012 (4)0.019 (4)
N10.0435 (18)0.0249 (18)0.0315 (16)0.0065 (14)0.0065 (13)0.0025 (14)
N20.0347 (16)0.035 (2)0.0308 (16)0.0029 (14)0.0029 (13)0.0004 (14)
N30.0448 (19)0.0267 (19)0.0380 (18)0.0004 (15)0.0080 (14)0.0088 (15)
N40.0384 (18)0.036 (2)0.0442 (19)0.0012 (15)0.0019 (15)0.0044 (16)
N50.044 (2)0.056 (3)0.053 (2)0.0053 (19)0.0113 (17)0.0008 (19)
N60.050 (2)0.067 (3)0.069 (3)0.009 (2)0.017 (2)0.004 (2)
N70.044 (2)0.058 (3)0.073 (3)0.0083 (19)0.0047 (19)0.003 (2)
N80.0447 (19)0.040 (2)0.0316 (17)0.0062 (16)0.0012 (14)0.0003 (15)
N90.051 (2)0.044 (2)0.0373 (19)0.0098 (17)0.0034 (16)0.0010 (17)
N100.0360 (18)0.045 (2)0.0394 (19)0.0105 (16)0.0005 (14)0.0056 (17)
N110.0391 (17)0.0312 (19)0.0309 (16)0.0037 (14)0.0039 (13)0.0019 (14)
N120.061 (2)0.030 (2)0.0422 (19)0.0105 (17)0.0078 (16)0.0026 (16)
N130.063 (2)0.031 (2)0.050 (2)0.0104 (18)0.0089 (17)0.0032 (17)
N140.050 (2)0.033 (2)0.044 (2)0.0061 (16)0.0068 (16)0.0084 (16)
N150.0329 (16)0.0305 (19)0.0307 (16)0.0013 (14)0.0011 (13)0.0039 (14)
N160.0366 (16)0.0267 (18)0.0317 (16)0.0029 (14)0.0017 (13)0.0082 (14)
N170.0471 (19)0.034 (2)0.0358 (18)0.0073 (16)0.0087 (14)0.0036 (15)
N180.071 (2)0.044 (2)0.0368 (19)0.0136 (19)0.0109 (17)0.0083 (17)
N190.076 (3)0.047 (3)0.046 (2)0.014 (2)0.0137 (19)0.0135 (19)
N200.057 (2)0.041 (2)0.047 (2)0.0121 (18)0.0066 (17)0.0124 (18)
N210.0410 (19)0.052 (3)0.055 (2)0.0033 (17)0.0032 (16)0.0104 (19)
C10.034 (2)0.032 (2)0.041 (2)0.0025 (17)0.0005 (16)0.0072 (18)
C20.0342 (19)0.035 (2)0.033 (2)0.0006 (17)0.0030 (15)0.0067 (17)
C30.039 (2)0.033 (2)0.0305 (19)0.0056 (18)0.0023 (16)0.0039 (17)
C40.048 (2)0.030 (2)0.046 (2)0.0005 (19)0.0084 (19)0.0078 (19)
C50.038 (2)0.033 (2)0.032 (2)0.0040 (17)0.0018 (16)0.0053 (17)
C60.057 (2)0.025 (2)0.034 (2)0.0067 (19)0.0107 (18)0.0009 (17)
C70.049 (2)0.049 (3)0.036 (2)0.005 (2)0.0057 (18)0.011 (2)
C80.047 (2)0.051 (3)0.042 (2)0.002 (2)0.0056 (19)0.002 (2)
C90.036 (2)0.034 (2)0.035 (2)0.0012 (17)0.0063 (16)0.0056 (18)
C100.040 (2)0.034 (2)0.042 (2)0.0049 (18)0.0035 (17)0.0088 (19)
C110.036 (2)0.036 (2)0.035 (2)0.0007 (17)0.0028 (16)0.0017 (18)
C120.049 (2)0.048 (3)0.030 (2)0.000 (2)0.0014 (17)0.0009 (19)
C130.036 (2)0.038 (2)0.0295 (19)0.0044 (17)0.0014 (15)0.0005 (18)
C140.049 (2)0.032 (2)0.028 (2)0.0080 (18)0.0067 (17)0.0012 (17)
C150.064 (3)0.039 (3)0.033 (2)0.009 (2)0.0019 (19)0.0039 (19)
C160.041 (2)0.034 (3)0.057 (3)0.0005 (19)0.005 (2)0.008 (2)
C170.059 (3)0.038 (3)0.041 (2)0.004 (2)0.003 (2)0.001 (2)
C180.066 (3)0.036 (3)0.060 (3)0.017 (2)0.003 (2)0.000 (2)
C190.064 (3)0.040 (3)0.042 (2)0.005 (2)0.009 (2)0.004 (2)
C200.061 (3)0.059 (3)0.038 (2)0.010 (2)0.008 (2)0.003 (2)
C210.060 (3)0.070 (4)0.028 (2)0.010 (2)0.0050 (19)0.006 (2)
C220.056 (3)0.045 (3)0.067 (3)0.015 (2)0.016 (2)0.003 (2)
C230.078 (3)0.038 (3)0.055 (3)0.018 (2)0.001 (2)0.008 (2)
C240.082 (4)0.049 (3)0.056 (3)0.012 (3)0.022 (3)0.007 (2)
C250.051 (2)0.050 (3)0.046 (2)0.008 (2)0.0021 (19)0.013 (2)
C260.052 (3)0.042 (3)0.049 (3)0.004 (2)0.003 (2)0.008 (2)
C270.043 (2)0.076 (4)0.060 (3)0.012 (2)0.006 (2)0.024 (3)
C280.045 (2)0.046 (3)0.076 (3)0.004 (2)0.009 (2)0.020 (3)
C290.067 (3)0.066 (4)0.053 (3)0.011 (3)0.013 (2)0.008 (3)
C300.043 (3)0.083 (4)0.071 (3)0.000 (3)0.002 (2)0.016 (3)
C310.065 (3)0.053 (3)0.082 (4)0.015 (3)0.016 (3)0.032 (3)
C320.075 (4)0.077 (4)0.079 (4)0.005 (3)0.033 (3)0.020 (3)
C330.086 (4)0.100 (6)0.113 (5)0.010 (4)0.026 (4)0.062 (5)
C340.123 (6)0.063 (5)0.185 (8)0.004 (4)0.057 (6)0.050 (5)
C350.051 (3)0.071 (4)0.141 (6)0.003 (3)0.007 (3)0.046 (4)
C360.051 (3)0.063 (4)0.098 (4)0.013 (3)0.007 (3)0.026 (3)
C370.051 (3)0.048 (3)0.118 (5)0.002 (2)0.007 (3)0.004 (3)
C380.054 (3)0.077 (5)0.155 (7)0.001 (3)0.009 (4)0.032 (5)
C390.063 (4)0.137 (8)0.200 (9)0.025 (4)0.032 (5)0.065 (7)
C400.107 (6)0.047 (5)0.265 (12)0.011 (4)0.033 (7)0.004 (6)
C410.164 (13)0.155 (14)0.217 (15)0.103 (11)0.017 (11)0.113 (12)
Geometric parameters (Å, º) top
Fe1—N42.143 (3)C15—C201.379 (7)
Fe1—N22.151 (3)C15—H150.9300
Fe1—N172.161 (3)C17—C231.373 (6)
Fe1—N112.166 (3)C17—H170.9300
Fe1—N32.312 (3)C18—C231.373 (6)
Fe1—N12.318 (3)C18—H180.9300
Fe1—N162.337 (3)C19—C241.368 (7)
Fe1—N152.341 (3)C19—H190.9300
O1—H1O10.8501C20—H200.9300
O1—H2O10.8500C21—H210.9300
O2—H1O20.8500C22—C241.370 (7)
O2—H2O20.8500C22—H220.9300
O3—C411.484 (15)C23—H230.9300
O3—H30.8200C24—H240.9300
N1—C31.341 (5)C25—C261.497 (6)
N1—C141.345 (5)C25—H25A0.9700
N2—C51.326 (5)C25—H25B0.9700
N2—N81.355 (4)C26—C291.516 (6)
N3—C61.335 (5)C26—H26A0.9700
N3—C41.346 (5)C26—H26B0.9700
N4—C161.341 (5)C27—C311.519 (8)
N4—N51.345 (5)C27—H27A0.9700
N5—N61.303 (5)C27—H27B0.9700
N6—N71.362 (6)C28—C361.490 (7)
N7—C161.317 (6)C28—H28A0.9700
N8—N91.297 (5)C28—H28B0.9700
N9—N101.353 (5)C29—C321.498 (8)
N10—C51.321 (5)C29—H29A0.9700
N11—C91.334 (5)C29—H29B0.9700
N11—N121.342 (4)C30—C371.497 (8)
N12—N131.314 (5)C30—H30A0.9700
N13—N141.351 (5)C30—H30B0.9700
N14—C91.312 (5)C31—C331.505 (8)
N15—C21.330 (5)C31—H31A0.9700
N15—C131.345 (5)C31—H31B0.9700
N16—C111.332 (5)C32—H32A0.9600
N16—C11.343 (5)C32—H32B0.9600
N17—C101.333 (5)C32—H32C0.9600
N17—N181.349 (4)C33—C341.512 (10)
N18—N191.315 (5)C33—H33A0.9700
N19—N201.352 (5)C33—H33B0.9700
N20—C101.316 (5)C34—H34A0.9600
N21—C281.513 (6)C34—H34B0.9600
N21—C271.517 (6)C34—H34C0.9600
N21—C301.519 (6)C35—C391.481 (9)
N21—C251.519 (5)C35—C361.517 (7)
C1—C181.385 (6)C35—H35A0.9700
C1—C101.452 (5)C35—H35B0.9700
C2—C71.392 (5)C36—H36A0.9700
C2—C91.457 (5)C36—H36B0.9700
C3—C81.383 (6)C37—C381.517 (8)
C3—C51.462 (5)C37—H37A0.9700
C4—C221.380 (6)C37—H37B0.9700
C4—C161.452 (6)C38—C401.510 (12)
C6—C191.385 (6)C38—H38A0.9700
C6—C141.467 (6)C38—H38B0.9700
C7—C211.376 (6)C39—H39A0.9600
C7—H70.9300C39—H39B0.9600
C8—C201.380 (6)C39—H39C0.9600
C8—H80.9300C40—H40A0.9600
C11—C171.384 (6)C40—H40B0.9600
C11—C131.479 (6)C40—H40C0.9600
C12—C211.372 (6)C41—H41A0.9600
C12—C131.396 (5)C41—H41B0.9600
C12—H120.9300C41—H41C0.9600
C14—C151.374 (6)
N4—Fe1—N2150.92 (12)C23—C18—C1118.3 (4)
N4—Fe1—N1793.73 (13)C23—C18—H18120.8
N2—Fe1—N1793.74 (13)C1—C18—H18120.8
N4—Fe1—N1192.76 (13)C24—C19—C6118.4 (4)
N2—Fe1—N1193.34 (12)C24—C19—H19120.8
N17—Fe1—N11152.73 (12)C6—C19—H19120.8
N4—Fe1—N371.40 (12)C15—C20—C8120.0 (4)
N2—Fe1—N3137.68 (12)C15—C20—H20120.0
N17—Fe1—N378.35 (12)C8—C20—H20120.0
N11—Fe1—N378.71 (11)C12—C21—C7120.4 (4)
N4—Fe1—N1138.59 (12)C12—C21—H21119.8
N2—Fe1—N170.48 (11)C7—C21—H21119.8
N17—Fe1—N178.68 (11)C24—C22—C4118.5 (5)
N11—Fe1—N178.96 (11)C24—C22—H22120.8
N3—Fe1—N167.20 (12)C4—C22—H22120.8
N4—Fe1—N1677.99 (12)C17—C23—C18120.1 (4)
N2—Fe1—N1678.17 (11)C17—C23—H23119.9
N17—Fe1—N1670.38 (11)C18—C23—H23119.9
N11—Fe1—N16136.89 (11)C19—C24—C22120.6 (4)
N3—Fe1—N16134.17 (11)C19—C24—H24119.7
N1—Fe1—N16133.88 (11)C22—C24—H24119.7
N4—Fe1—N1578.12 (11)C26—C25—N21116.6 (4)
N2—Fe1—N1577.30 (11)C26—C25—H25A108.1
N17—Fe1—N15137.06 (11)N21—C25—H25A108.1
N11—Fe1—N1570.21 (11)C26—C25—H25B108.1
N3—Fe1—N15134.86 (12)N21—C25—H25B108.1
N1—Fe1—N15133.47 (10)H25A—C25—H25B107.3
N16—Fe1—N1566.68 (10)C25—C26—C29112.2 (4)
H1O1—O1—H2O1107.7C25—C26—H26A109.2
H1O2—O2—H2O2107.7C29—C26—H26A109.2
C41—O3—H3111.3C25—C26—H26B109.2
C3—N1—C14119.6 (3)C29—C26—H26B109.2
C3—N1—Fe1118.5 (2)H26A—C26—H26B107.9
C14—N1—Fe1122.0 (3)N21—C27—C31114.7 (4)
C5—N2—N8104.9 (3)N21—C27—H27A108.6
C5—N2—Fe1121.3 (2)C31—C27—H27A108.6
N8—N2—Fe1133.8 (2)N21—C27—H27B108.6
C6—N3—C4119.6 (3)C31—C27—H27B108.6
C6—N3—Fe1122.6 (3)H27A—C27—H27B107.6
C4—N3—Fe1117.8 (3)C36—C28—N21117.8 (4)
C16—N4—N5105.6 (3)C36—C28—H28A107.9
C16—N4—Fe1120.0 (3)N21—C28—H28A107.9
N5—N4—Fe1134.4 (3)C36—C28—H28B107.9
N6—N5—N4108.1 (4)N21—C28—H28B107.9
N5—N6—N7110.6 (4)H28A—C28—H28B107.2
C16—N7—N6104.0 (4)C32—C29—C26114.6 (4)
N9—N8—N2108.6 (3)C32—C29—H29A108.6
N8—N9—N10110.1 (3)C26—C29—H29A108.6
C5—N10—N9104.3 (3)C32—C29—H29B108.6
C9—N11—N12105.7 (3)C26—C29—H29B108.6
C9—N11—Fe1121.0 (2)H29A—C29—H29B107.6
N12—N11—Fe1133.3 (2)C37—C30—N21116.6 (5)
N13—N12—N11107.7 (3)C37—C30—H30A108.1
N12—N13—N14110.5 (3)N21—C30—H30A108.1
C9—N14—N13104.2 (3)C37—C30—H30B108.1
C2—N15—C13119.8 (3)N21—C30—H30B108.1
C2—N15—Fe1118.1 (2)H30A—C30—H30B107.3
C13—N15—Fe1122.1 (2)C33—C31—C27113.6 (5)
C11—N16—C1119.3 (3)C33—C31—H31A108.8
C11—N16—Fe1123.0 (2)C27—C31—H31A108.8
C1—N16—Fe1117.7 (2)C33—C31—H31B108.8
C10—N17—N18105.8 (3)C27—C31—H31B108.8
C10—N17—Fe1121.2 (3)H31A—C31—H31B107.7
N18—N17—Fe1132.7 (3)C29—C32—H32A109.5
N19—N18—N17107.2 (3)C29—C32—H32B109.5
N18—N19—N20110.9 (3)H32A—C32—H32B109.5
C10—N20—N19104.0 (3)C29—C32—H32C109.5
C28—N21—C27110.3 (3)H32A—C32—H32C109.5
C28—N21—C30110.3 (4)H32B—C32—H32C109.5
C27—N21—C30107.5 (4)C31—C33—C34112.6 (6)
C28—N21—C25106.4 (3)C31—C33—H33A109.1
C27—N21—C25110.6 (4)C34—C33—H33A109.1
C30—N21—C25111.7 (3)C31—C33—H33B109.1
N16—C1—C18121.8 (4)C34—C33—H33B109.1
N16—C1—C10112.5 (3)H33A—C33—H33B107.8
C18—C1—C10125.7 (4)C33—C34—H34A109.5
N15—C2—C7122.6 (4)C33—C34—H34B109.5
N15—C2—C9112.4 (3)H34A—C34—H34B109.5
C7—C2—C9124.9 (4)C33—C34—H34C109.5
N1—C3—C8122.5 (4)H34A—C34—H34C109.5
N1—C3—C5111.5 (3)H34B—C34—H34C109.5
C8—C3—C5126.0 (4)C39—C35—C36113.9 (6)
N3—C4—C22121.4 (4)C39—C35—H35A108.8
N3—C4—C16111.7 (4)C36—C35—H35A108.8
C22—C4—C16126.9 (4)C39—C35—H35B108.8
N10—C5—N2112.1 (3)C36—C35—H35B108.8
N10—C5—C3129.6 (4)H35A—C35—H35B107.7
N2—C5—C3118.3 (3)C28—C36—C35109.8 (5)
N3—C6—C19121.6 (4)C28—C36—H36A109.7
N3—C6—C14114.2 (3)C35—C36—H36A109.7
C19—C6—C14124.3 (4)C28—C36—H36B109.7
C21—C7—C2117.6 (4)C35—C36—H36B109.7
C21—C7—H7121.2H36A—C36—H36B108.2
C2—C7—H7121.2C30—C37—C38112.3 (6)
C20—C8—C3117.5 (4)C30—C37—H37A109.1
C20—C8—H8121.2C38—C37—H37A109.1
C3—C8—H8121.2C30—C37—H37B109.1
N14—C9—N11112.0 (3)C38—C37—H37B109.1
N14—C9—C2129.8 (3)H37A—C37—H37B107.9
N11—C9—C2118.2 (3)C40—C38—C37113.1 (7)
N20—C10—N17112.0 (3)C40—C38—H38A109.0
N20—C10—C1129.8 (4)C37—C38—H38A109.0
N17—C10—C1118.2 (3)C40—C38—H38B109.0
N16—C11—C17121.8 (4)C37—C38—H38B109.0
N16—C11—C13113.8 (3)H38A—C38—H38B107.8
C17—C11—C13124.3 (4)C35—C39—H39A109.5
C21—C12—C13119.1 (4)C35—C39—H39B109.5
C21—C12—H12120.4H39A—C39—H39B109.5
C13—C12—H12120.4C35—C39—H39C109.5
N15—C13—C12120.5 (4)H39A—C39—H39C109.5
N15—C13—C11114.3 (3)H39B—C39—H39C109.5
C12—C13—C11125.2 (4)C38—C40—H40A109.5
N1—C14—C15120.7 (4)C38—C40—H40B109.5
N1—C14—C6114.1 (3)H40A—C40—H40B109.5
C15—C14—C6125.2 (4)C38—C40—H40C109.5
C14—C15—C20119.6 (4)H40A—C40—H40C109.5
C14—C15—H15120.2H40B—C40—H40C109.5
C20—C15—H15120.2O3—C41—H41A109.5
N7—C16—N4111.7 (4)O3—C41—H41B109.5
N7—C16—C4129.2 (4)H41A—C41—H41B109.5
N4—C16—C4119.0 (4)O3—C41—H41C109.5
C23—C17—C11118.6 (4)H41A—C41—H41C109.5
C23—C17—H17120.7H41B—C41—H41C109.5
C11—C17—H17120.7
C16—N4—N5—N61.0 (5)C1—N16—C11—C170.2 (6)
Fe1—N4—N5—N6179.1 (3)Fe1—N16—C11—C17179.8 (3)
N4—N5—N6—N70.9 (5)C1—N16—C11—C13179.0 (3)
N5—N6—N7—C160.4 (6)Fe1—N16—C11—C130.6 (5)
C5—N2—N8—N90.2 (4)C2—N15—C13—C121.7 (6)
Fe1—N2—N8—N9179.8 (3)Fe1—N15—C13—C12177.3 (3)
N2—N8—N9—N100.0 (5)C2—N15—C13—C11179.1 (3)
N8—N9—N10—C50.2 (4)Fe1—N15—C13—C111.9 (4)
C9—N11—N12—N130.3 (4)C21—C12—C13—N151.7 (6)
Fe1—N11—N12—N13180.0 (3)C21—C12—C13—C11179.2 (4)
N11—N12—N13—N140.3 (5)N16—C11—C13—N150.8 (5)
N12—N13—N14—C90.1 (5)C17—C11—C13—N15178.4 (4)
C10—N17—N18—N190.2 (5)N16—C11—C13—C12178.3 (4)
Fe1—N17—N18—N19173.9 (3)C17—C11—C13—C122.5 (7)
N17—N18—N19—N200.3 (5)C3—N1—C14—C150.1 (5)
N18—N19—N20—C100.3 (5)Fe1—N1—C14—C15179.6 (3)
C11—N16—C1—C180.0 (6)C3—N1—C14—C6179.7 (3)
Fe1—N16—C1—C18179.6 (3)Fe1—N1—C14—C60.6 (4)
C11—N16—C1—C10179.6 (3)N3—C6—C14—N10.2 (5)
Fe1—N16—C1—C100.8 (4)C19—C6—C14—N1179.2 (4)
C13—N15—C2—C70.0 (6)N3—C6—C14—C15180.0 (4)
Fe1—N15—C2—C7179.0 (3)C19—C6—C14—C150.6 (7)
C13—N15—C2—C9179.6 (3)N1—C14—C15—C200.2 (6)
Fe1—N15—C2—C90.6 (4)C6—C14—C15—C20179.6 (4)
C14—N1—C3—C80.3 (6)N6—N7—C16—N40.2 (5)
Fe1—N1—C3—C8180.0 (3)N6—N7—C16—C4178.1 (4)
C14—N1—C3—C5179.4 (3)N5—N4—C16—N70.8 (5)
Fe1—N1—C3—C50.3 (4)Fe1—N4—C16—N7179.2 (3)
C6—N3—C4—C220.4 (6)N5—N4—C16—C4177.8 (4)
Fe1—N3—C4—C22179.4 (3)Fe1—N4—C16—C40.7 (5)
C6—N3—C4—C16179.2 (3)N3—C4—C16—N7178.2 (4)
Fe1—N3—C4—C160.6 (4)C22—C4—C16—N70.5 (8)
N9—N10—C5—N20.3 (4)N3—C4—C16—N40.0 (5)
N9—N10—C5—C3179.4 (4)C22—C4—C16—N4178.7 (4)
N8—N2—C5—N100.3 (4)N16—C11—C17—C230.7 (7)
Fe1—N2—C5—N10179.7 (3)C13—C11—C17—C23178.5 (4)
N8—N2—C5—C3179.5 (3)N16—C1—C18—C230.1 (7)
Fe1—N2—C5—C30.5 (5)C10—C1—C18—C23179.7 (4)
N1—C3—C5—N10179.1 (4)N3—C6—C19—C241.1 (7)
C8—C3—C5—N100.6 (7)C14—C6—C19—C24179.5 (4)
N1—C3—C5—N20.1 (5)C14—C15—C20—C80.1 (7)
C8—C3—C5—N2179.6 (4)C3—C8—C20—C150.4 (7)
C4—N3—C6—C190.5 (6)C13—C12—C21—C70.1 (7)
Fe1—N3—C6—C19179.7 (3)C2—C7—C21—C121.4 (7)
C4—N3—C6—C14179.9 (3)N3—C4—C22—C240.5 (7)
Fe1—N3—C6—C140.3 (4)C16—C4—C22—C24179.2 (4)
N15—C2—C7—C211.5 (6)C11—C17—C23—C180.8 (8)
C9—C2—C7—C21178.0 (4)C1—C18—C23—C170.6 (8)
N1—C3—C8—C200.5 (6)C6—C19—C24—C220.9 (8)
C5—C3—C8—C20179.1 (4)C4—C22—C24—C190.1 (8)
N13—N14—C9—N110.1 (5)C28—N21—C25—C26178.9 (4)
N13—N14—C9—C2178.9 (4)C27—N21—C25—C2659.0 (5)
N12—N11—C9—N140.3 (5)C30—N21—C25—C2660.6 (5)
Fe1—N11—C9—N14180.0 (3)N21—C25—C26—C29175.9 (4)
N12—N11—C9—C2178.8 (3)C28—N21—C27—C3157.9 (5)
Fe1—N11—C9—C20.9 (5)C30—N21—C27—C31178.2 (4)
N15—C2—C9—N14179.9 (4)C25—N21—C27—C3159.6 (5)
C7—C2—C9—N140.3 (7)C27—N21—C28—C3653.9 (6)
N15—C2—C9—N111.0 (5)C30—N21—C28—C3664.7 (6)
C7—C2—C9—N11178.6 (4)C25—N21—C28—C36173.9 (4)
N19—N20—C10—N170.2 (5)C25—C26—C29—C32172.5 (4)
N19—N20—C10—C1178.8 (4)C28—N21—C30—C3763.5 (5)
N18—N17—C10—N200.0 (5)C27—N21—C30—C37176.2 (4)
Fe1—N17—C10—N20174.9 (3)C25—N21—C30—C3754.7 (6)
N18—N17—C10—C1179.1 (4)N21—C27—C31—C33170.7 (4)
Fe1—N17—C10—C14.2 (5)C27—C31—C33—C34176.2 (5)
N16—C1—C10—N20176.9 (4)N21—C28—C36—C35170.9 (4)
C18—C1—C10—N203.5 (8)C39—C35—C36—C28176.7 (6)
N16—C1—C10—N172.0 (5)N21—C30—C37—C38171.9 (4)
C18—C1—C10—N17177.6 (4)C30—C37—C38—C40175.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C37—H37A···N7i0.972.703.558 (7)148
C28—H28B···O2ii0.972.423.385 (6)172
C19—H19···N12iii0.932.633.528 (6)163
C17—H17···N9iv0.932.683.597 (5)168
C17—H17···N8iv0.932.553.456 (5)163
C15—H15···N12iii0.932.553.458 (5)165
C12—H12···N8iv0.932.663.572 (5)166
O2—H2O2···O1v0.851.962.802 (5)169
O2—H1O2···N200.852.042.878 (5)166
O1—H2O1···N19vi0.852.323.021 (5)140
O1—H1O1···N100.852.322.921 (5)128
O1—H1O1···N100.852.322.921 (5)128
O1—H2O1···N19vi0.852.323.021 (5)140
O2—H1O2···N200.852.042.878 (5)166
O2—H2O2···O1v0.851.962.802 (5)169
C12—H12···N8iv0.932.663.572 (5)166
C15—H15···N12iii0.932.553.458 (5)165
C17—H17···N8iv0.932.553.456 (5)163
C17—H17···N9iv0.932.683.597 (5)168
C19—H19···N12iii0.932.633.528 (6)163
C28—H28B···O2ii0.972.423.385 (6)172
C37—H37A···N7i0.972.703.558 (7)148
O1—H1O1···N100.852.322.921 (5)128
O1—H2O1···N19vi0.852.323.021 (5)140
O2—H1O2···N200.852.042.878 (5)166
O2—H2O2···O1v0.851.962.802 (5)169
C12—H12···N8iv0.932.663.572 (5)166
C15—H15···N12iii0.932.553.458 (5)165
C17—H17···N8iv0.932.553.456 (5)163
C17—H17···N9iv0.932.683.597 (5)168
C19—H19···N12iii0.932.633.528 (6)163
C28—H28B···O2ii0.972.423.385 (6)172
C37—H37A···N7i0.972.703.558 (7)148
O1—H1O1···N100.852.322.921 (5)128
O1—H2O1···N19vi0.852.323.021 (5)140
O2—H1O2···N200.852.042.878 (5)166
O2—H2O2···O1v0.851.962.802 (5)169
C12—H12···N8iv0.932.663.572 (5)166
C15—H15···N12iii0.932.553.458 (5)165
C17—H17···N8iv0.932.553.456 (5)163
C17—H17···N9iv0.932.683.597 (5)168
C19—H19···N12iii0.932.633.528 (6)163
C28—H28B···O2ii0.972.423.385 (6)172
C37—H37A···N7i0.972.703.558 (7)148
O1—H1O1···N100.852.322.921 (5)128
O1—H2O1···N19vi0.852.323.021 (5)140
O2—H1O2···N200.852.042.878 (5)166
O2—H2O2···O1v0.851.962.802 (5)169
C12—H12···N8iv0.932.663.572 (5)166
C15—H15···N12iii0.932.553.458 (5)165
C17—H17···N8iv0.932.553.456 (5)163
C17—H17···N9iv0.932.683.597 (5)168
C19—H19···N12iii0.932.633.528 (6)163
C28—H28B···O2ii0.972.423.385 (6)172
C37—H37A···N7i0.972.703.558 (7)148
Symmetry codes: (i) x+1, y1, z; (ii) x+1, y, z; (iii) x+1, y+2, z; (iv) x+1, y+1, z+1; (v) x1, y, z; (vi) x+1, y+1, z.
 

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