Issue contents cross.png
Download PDF of article cross.png
Download CIF cross.png
3D view cross.png
Navigation cross.png
Highlighting cross.png
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation cross.png
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
Text
cross.png
share
Previous article cross.png
Next article cross.png
Previous article cross.png
Issue contents cross.png
Download PDF of article cross.png
Download CIF cross.png
3D view cross.png
Navigation cross.png
Highlighting cross.png
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation cross.png
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
Text
cross.png
share
Next article cross.png

metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 6| Part 5| May 2021|
https://doi.org/10.1107/S2414314621005319

Bis(1-methyl­imidazole)[meso-α,α,α,α-tetra­kis(o-nicotinamido­phen­yl)porphinato]iron(II)–1-methyl­imidazole–tetra­hydro­furan (1/1/1.5)

crossmark logo
Yingying Fana and Jianfeng Lia*

aCollege of Materials Science and Optoelectronic Technology, CAS Center for Excellence in Topological Quantum Computation & Center of Materials Science and Optoelectronics Engineering, University of Chinese Academy of Sciences, Yanqi Lake, Huairou District, Beijing, 101408, People's Republic of China
*Correspondence e-mail: jfli@ucas.ac.cn

Edited by S. Bernès, Benemérita Universidad Autónoma de Puebla, México (Received 11 March 2021; accepted 19 May 2021; online 25 May 2021)

In the title compound, [FeII(C68H44N12O4)(C4H6N2)2]·C4H6N2·1.5C4H8O, the central FeII ion is coordinated by four pyrrole N atoms of the porphyrin core and two N atoms of the 1-methyl­imidazole ligands in the axial sites. One 1-methyl­imidazole and one and a half tetra­hydro­furan solvent mol­ecules are also present in the asymmetric unit. The complex exhibits a near planar porphyrin core conformation, in which the iron centre is slightly displaced towards the hindered porphyrin side (0.01 Å). The average Fe—Np (Np refers to the pyrrole nitro­gen atoms in the porphyrin) bond length is 1.990 (9) Å, and the axial Fe—NIm (NIm refers to the imidazole nitro­gen atoms) bond lengths are 1.993 (3) and 2.004 (3) Å. The dihedral angle between the two coordinated 1-methyl­imidazole planes is 56.6 (2)°. The dihedral angles between the 1-methyl­imidazole planes and the planes of the closest Fe—Np vector are 16.8 (2) and 39.8 (2)°. N—H⋯N and N—H⋯O inter­actions are observed in the crystal structure.

CCDC reference: 2068473

Similar articles
3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Heme a is an important redox site of cytochrome c oxidases (CcO) (Pitcher & Watmough, 2004[Pitcher, R. S. & Watmough, N. J. (2004). Biochim. Biophys. Acta, 1655, 388-399.]), and bis­(imidazole)–iron(II) porphyrin complexes are used to understand the relationship between its structure and function (Walker, 2004[Walker, F. A. (2004). Chem. Rev. 104, 589-616.]). The picket-fence species with bis­(imidazole)-ligated groups is one of the effective models to study the effect of axial ligand orientation. Crystal structures of bis­(imidazole)-ligated iron(II) picket-fence porphyrinates, e.g. [Fe(TpivPP)(1-RIm)2] (TpivPP = α,α,α,α-tetra­kis­(o-pivalamido­phen­yl)porphyrin; 1-RIm = 1-methyl-, 1-ethyl-, or 1-vinyl­imidazole; Li et al., 2008[Li, J., Nair, S. M., Noll, B. C., Schulz, C. E. & Scheidt, W. R. (2008). Inorg. Chem. 47, 3841-3850.]), [Fe(TImPP)(1-RIm)2] (TImPP = α,α,α,α-o-(1-methyl­imid­azole-5-carboxyl­amino­phen­yl)porphyrin; 1-RIm = 1-methyl- or 1-ethyl­imidazole; Yao et al., 2017[Yao, Z., Schulz, C. E., Zhan, N. & Li, J. (2017). Inorg. Chem. 56, 12615-12624.]) and [Fe(MbenTpivPP)(1-MeIm)2] (MbenTpivPP = meso-mono[α-o-(benzene­carb­ox­amido)­phen­yl]tris­[α,α,α-o-(pivalamido­phen­yl)]porphyrin; 1-MeIm = 1-methyl­imidazole; He et al., 2015[He, B., Schulz, C. E. & Li, J. (2015). Dalton Trans. 44, 13651-13661.]) have been determined. Herein, the crystal structure of a new iron(II) porphyrin solvated complex, [Fe(C68H44N12O4)(C4H6N2)2]·C4H6N2·1.5C4H8O is reported.

The asymmetric unit of the title compound (Fig. 1[link]) contains one bis­(1-methyl­imidazole)[meso-α,α,α,α-tetra­kis­(o-nicotin­am­ido­phen­yl)porphinato]iron(II), one 1-methyl­imidazole and one and a half tetra­hydro­furan lattice solvate mol­ecules. Additional qu­anti­tative information on the structure is given in Fig. 2[link], which displays the detailed displacement of each porphyrin core atom (in units of 0.01 Å) from the 24-atom mean plane. Averaged values of the chemically unique bond lengths (Å) and angles (°) are also shown. The title compound has a near planar porphyrin core conformation, in which the iron centre is slightly displaced towards the hindered porphyrin side (0.01 Å). The dihedral angles formed by the 1-MeIm axial ligand planes and the closest Fe—Np vector are 16.8 (2) and 39.8 (2)°. The dihedral angle between the two coordinated imidazole planes is 56.6 (2)°, showing a relative perpendicular orientation. Fig. 2[link] also shows that the average Np—Fe—Np angle is ideal at 90.01 (9)°, and the axial Fe—NIm bond lengths are 1.993 (3) and 2.004 (3) Å. The average Fe—Np distance of 1.990 (9) Å is a typical value for low-spin ferrous porphyrin derivatives (Scheidt & Reed, 1981[Scheidt, W. R. & Reed, C. A. (1981). Chem. Rev. 81, 543-555.]).

[Figure 1]
Figure 1
The mol­ecular entities in the title compound, with displacement ellipsoids drawn at the 25% probability level. The 1-methyl­imidazole and tetra­hydro­furan solvent mol­ecules are omitted for clarity.
[Figure 2]
Figure 2
A formal diagram of the porphyrinato core of the title compound. Averaged values of the chemically unique bond distances (in Å) and angles (°) are shown. The numbers in parentheses are the e.s.d.'s calculated on the assumption that the averaged values were all drawn from the same population. The perpendicular displacements (in units of 0.01 Å) of the porphyrin core atoms from the 24-atom mean plane are also displayed. Positive values of the displacement are towards the hindered porphyrin side. The dashed line indicates the imidazole on the less hindered porphyrin side and the circles represent the positions of the methyl groups on the axial ligands.

Several intra- and inter-mol­ecular inter­actions are found in the title compound. As can be seen in Table 1[link] and Fig. 3[link], the distance between N8 and N9, and the N8—H8⋯N9 angle are 3.018 (5) Å and 156°, respectively, in agreement with reported values of 2.6 < N⋯N′ < 3.2 Å and 131.5 < N—H⋯N′ < 179.7° (Prasad & Govil, 1980[Prasad, N. & Govil, G. (1980). Proc. Indian Acad. Sci. Chem. Sci. 89, 253-262.]; Aldilla et al., 2017[Aldilla, V. R., Bhadbhade, M., Bhattacharyya, S., Kumar, N., Rich, A. M. & Marjo, C. E. (2017). CrystEngComm, 19, 4749-4758.]; Leigh et al., 2013[Leigh, D. A., Robertson, C. C., Slawin, A. M. Z. & Thomson, P. I. T. (2013). J. Am. Chem. Soc. 135, 9939-9943.]). The distance between N6 and O4, and the N6—H6⋯O4 angle are 2.948 (4) Å and 145°, respectively, consistent with the N—H⋯O inter­action of 2.7 < N⋯O < 3.05 Å and N—H⋯O > 130° (Bertolasi et al., 1995[Bertolasi, V., Gilli, P., Ferretti, V. & Gilli, G. (1995). Acta Cryst. B51, 1004-1015.]; Malinovskii et al., 2001[Malinovskii, S. T., Simonov, Y. A. & Ganin, É. V. (2001). Crystallogr. Rep. 46, 419-424.]). The packing structure (Fig. 4[link]) shows that lattice solvent is placed in the voids left by the main mol­ecules in the crystal.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N6—H6⋯O4i 0.88 2.18 2.948 (4) 145
N8—H8⋯N9 0.88 2.19 3.018 (5) 156
Symmetry code: (i) x, y+1, z.
[Figure 3]
Figure 3
N—H⋯O and N—H⋯N inter­actions in the crystal structure of the title compound (see Table 1[link]).
[Figure 4]
Figure 4
A view of the mol­ecular packing of the title compound. Hydrogen atoms are omitted for clarity.

Synthesis and crystallization

General information. All reactions and manipulations were carried out under argon using a double-manifold vacuum line and Schlenk wares. Tetra­hydro­furan (THF) was distilled from Na/benzo­phenone under N2. Hexanes were distilled over sodium/potassium alloy under N2. Solvents were degassed by repeated freeze–pump–thaw cycles. 1-MeIm was distilled under argon before use. Precursors H2TPyPP, [Fe(TPyPP)]Cl, and [Fe(TPyPP)]OH were prepared following literature methods (Gunter et al., 1984[Gunter, M. J., McLaughlin, G. M., Berry, K. J., Murray, K. S., Irving, M. & Clark, P. E. (1984). Inorg. Chem. 23, 283-300.]; TPyPP is o-nicotinamido­phen­yl), with slight modifications.

Synthesis of the title compound. [Fe(TPyPP)]OH (10 mg, 8.6 × 10−3 mmol) and 1-MeIm (0.14 ml, 1.7 × 10 −3 mol) were dissolved in 3 ml of THF. The mixture was stirred for 15 min and transferred into glass tubes (8 mm × 10 cm), which were layered with hexa­nes. Several days later, X-ray quality black block-shaped crystals were collected.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The atoms of THF mol­ecules (O5, C77, C78, C79, C80 and O6, C81, C82, C83, C84) exhibited unusual thermal motions and were thus restrained using the RIGU, ISOR and DFIX commands (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]). The O6⋯C84 THF mol­ecule was refined with a fixed occupancy of 1/2. Seven outlier reflections were omitted in the last cycles of refinement.

Table 2
Experimental details

Crystal data
Chemical formula [Fe(C68H44N12O4)(C4H6N2)2]·C4H6N2·1.5C4H8O
Mr 1503.48
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 100
a, b, c (Å) 13.0880 (18), 13.8413 (18), 22.771 (3)
α, β, γ (°) 75.588 (5), 76.138 (4), 74.316 (4)
V (Å3) 3780.3 (9)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.27
Crystal size (mm) 0.55 × 0.16 × 0.07
 
Data collection
Diffractometer Bruker D8 QUEST System
Absorption correction Multi-scan (SADABS; Bruker, 2016[Bruker (2016). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.950, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections 67154, 16109, 11563
Rint 0.069
(sin θ/λ)max (Å−1) 0.634
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.070, 0.219, 1.03
No. of reflections 16109
No. of parameters 1022
No. of restraints 131
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 1.82, −0.80
Computer programs: APEX2 and SAINT (Bruker, 2013[Bruker (2013). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT2014/6 (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014/6 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), Mercury (Macrae et al., 2020[Macrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M. & Wood, P. A. (2020). J. Appl. Cryst. 53, 226-235.]) and enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]).

Structural data

CCDC reference: 2068473

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314621005319/bh4061sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621005319/bh4061Isup2.hkl

checkCIF report


Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT2014/6 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/6 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: enCIFer (Allen et al., 2004).

Bis(1-methylimidazole)[meso-α,α,α,α-tetrakis(o-\ nicotinamidophenyl)porphinato]iron(II)–1-methylimidazole–tetrahydrofuran (1/1/1.5) top
Crystal data top
[Fe(C68H44N12O4)(C4H6N2)2]·C4H6N2·1.5C4H8OZ = 2
Mr = 1503.48F(000) = 1572
Triclinic, P1Dx = 1.321 Mg m−3
a = 13.0880 (18) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.8413 (18) ÅCell parameters from 9990 reflections
c = 22.771 (3) Åθ = 2.3–26.6°
α = 75.588 (5)°µ = 0.27 mm−1
β = 76.138 (4)°T = 100 K
γ = 74.316 (4)°Block, black
V = 3780.3 (9) Å30.55 × 0.16 × 0.07 mm
Data collection top
Bruker D8 QUEST System
diffractometer		11563 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.069
φ and ω scansθmax = 26.8°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)		h = −16→16
Tmin = 0.950, Tmax = 0.981k = −17→17
67154 measured reflectionsl = −28→28
16109 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.070 w = 1/[σ2(Fo2) + (0.1118P)2 + 7.2076P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.219(Δ/σ)max = 0.001
S = 1.03Δρmax = 1.82 e Å−3
16109 reflectionsΔρmin = −0.80 e Å−3
1022 parametersExtinction correction: SHELXL2016/6 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
131 restraintsExtinction coefficient: 0.0029 (8)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Fe10.58466 (3)0.34410 (3)0.29656 (2)0.01633 (14)
O10.7193 (3)0.5115 (3)−0.03486 (13)0.0573 (9)
O20.9173 (2)0.5353 (2)0.37668 (12)0.0344 (6)
O30.8951 (2)0.0304 (2)0.35901 (12)0.0347 (6)
O40.7501 (2)−0.1694 (2)0.21998 (13)0.0394 (7)
N10.5234 (2)0.3438 (2)0.22501 (12)0.0194 (5)
N20.5694 (2)0.4958 (2)0.27220 (12)0.0187 (5)
N30.6423 (2)0.34404 (19)0.36965 (12)0.0166 (5)
N40.6033 (2)0.19258 (19)0.31977 (12)0.0177 (5)
N50.6301 (3)0.4986 (2)0.06434 (14)0.0350 (7)
H50.6354180.4611770.1013510.042*
N60.8048 (2)0.6503 (2)0.31729 (13)0.0238 (6)
H60.7951260.6820200.2797570.029*
N70.8873 (2)0.0955 (2)0.44292 (13)0.0242 (6)
H70.9175950.1309640.4581310.029*
N80.7052 (2)0.0007 (2)0.17919 (13)0.0262 (6)
H80.7288990.0574600.1652270.031*
N90.7835 (3)0.1828 (3)0.09547 (17)0.0411 (8)
N101.0454 (3)0.5801 (4)0.16177 (17)0.0543 (10)
N111.1474 (3)0.1740 (3)0.26412 (18)0.0489 (9)
N121.0272 (4)0.0024 (4)0.1888 (2)0.0707 (14)
N130.7336 (2)0.3273 (2)0.24526 (12)0.0219 (6)
N140.8756 (3)0.3565 (3)0.17385 (17)0.0467 (9)
N150.4359 (2)0.3608 (2)0.34675 (12)0.0185 (5)
N160.2869 (2)0.4160 (2)0.40966 (13)0.0266 (6)
C10.5042 (3)0.2616 (2)0.20833 (14)0.0205 (6)
C20.4499 (3)0.2975 (3)0.15633 (16)0.0265 (7)
H20.4274680.2563550.1363040.032*
C30.4368 (3)0.3998 (3)0.14125 (16)0.0276 (7)
H30.4024770.4444950.1091280.033*
C40.4847 (3)0.4285 (2)0.18296 (15)0.0229 (7)
C50.4974 (3)0.5279 (3)0.17715 (14)0.0230 (7)
C60.5386 (3)0.5577 (2)0.21915 (15)0.0225 (7)
C70.5532 (3)0.6593 (3)0.21309 (16)0.0291 (8)
H7A0.5408340.7149700.1795300.035*
C80.5878 (3)0.6607 (3)0.26386 (16)0.0281 (7)
H8A0.6022510.7179020.2736500.034*
C90.5987 (3)0.5586 (2)0.30055 (14)0.0196 (6)
C100.6347 (2)0.5280 (2)0.35650 (14)0.0188 (6)
C110.6556 (2)0.4266 (2)0.38797 (14)0.0182 (6)
C120.6964 (3)0.3938 (2)0.44465 (15)0.0215 (7)
H120.7137140.4362960.4660680.026*
C130.7057 (3)0.2925 (2)0.46181 (15)0.0210 (6)
H130.7295310.2496900.4978410.025*
C140.6722 (2)0.2609 (2)0.41477 (14)0.0174 (6)
C150.6697 (2)0.1605 (2)0.41657 (14)0.0167 (6)
C160.6398 (2)0.1296 (2)0.37062 (14)0.0178 (6)
C170.6468 (3)0.0238 (2)0.37023 (15)0.0223 (7)
H170.670880−0.0339830.4002840.027*
C180.6127 (3)0.0226 (2)0.31940 (15)0.0223 (7)
H180.608180−0.0360830.3065600.027*
C190.5842 (2)0.1280 (2)0.28786 (14)0.0189 (6)
C200.5373 (2)0.1593 (2)0.23558 (15)0.0199 (6)
C210.4763 (3)0.6027 (3)0.11916 (15)0.0260 (7)
C220.3913 (3)0.6880 (3)0.11910 (17)0.0315 (8)
H220.3433590.6981500.1567340.038*
C230.3747 (4)0.7590 (3)0.06523 (19)0.0412 (10)
H230.3162590.8172990.0659790.049*
C240.4445 (4)0.7437 (3)0.01048 (19)0.0432 (10)
H240.4332200.791659−0.0265800.052*
C250.5305 (4)0.6594 (3)0.00883 (18)0.0400 (10)
H250.5785840.650280−0.0289290.048*
C260.5459 (3)0.5882 (3)0.06286 (16)0.0310 (8)
C270.7031 (3)0.4618 (3)0.01773 (16)0.0351 (9)
C280.7651 (3)0.3536 (3)0.03375 (17)0.0331 (8)
C290.7316 (3)0.2810 (3)0.08406 (17)0.0327 (8)
H290.6676790.3027070.1121300.039*
C300.8741 (4)0.1540 (4)0.0558 (2)0.0518 (12)
H300.9121810.0844870.0630070.062*
C310.9149 (4)0.2203 (4)0.0050 (2)0.0603 (14)
H310.9800640.196685−0.0216510.072*
C320.8601 (4)0.3211 (4)−0.00666 (19)0.0463 (11)
H320.8865140.367822−0.0415890.056*
C330.6418 (3)0.6083 (2)0.38832 (14)0.0190 (6)
C340.5649 (3)0.6259 (3)0.44132 (15)0.0234 (7)
H340.5110340.5869480.4556650.028*
C350.5653 (3)0.6987 (3)0.47335 (16)0.0276 (7)
H350.5128160.7085960.5094800.033*
C360.6418 (3)0.7564 (3)0.45278 (17)0.0295 (8)
H360.6422180.8067270.4744670.035*
C370.7181 (3)0.7412 (3)0.40050 (17)0.0271 (7)
H370.7703270.7820010.3859060.033*
C380.7195 (3)0.6666 (2)0.36884 (15)0.0212 (7)
C390.9001 (3)0.5861 (3)0.32628 (16)0.0248 (7)
C400.9877 (3)0.5806 (3)0.27001 (16)0.0290 (8)
C410.9675 (3)0.5903 (4)0.21235 (19)0.0412 (10)
H410.8943410.6050870.2075760.049*
C421.1475 (4)0.5602 (4)0.1702 (2)0.0503 (12)
H421.2038900.5530550.1354160.060*
C431.1749 (3)0.5496 (3)0.2261 (2)0.0433 (10)
H431.2486050.5353370.2296570.052*
C441.0942 (3)0.5598 (3)0.27734 (19)0.0345 (8)
H441.1112310.5528250.3166830.041*
C450.6993 (3)0.0804 (2)0.47120 (15)0.0194 (6)
C460.6203 (3)0.0351 (3)0.51272 (16)0.0249 (7)
H460.5479630.0563040.5060110.030*
C470.6446 (3)−0.0399 (3)0.56352 (17)0.0301 (8)
H470.589642−0.0702650.5909950.036*
C480.7502 (3)−0.0705 (3)0.57402 (17)0.0337 (8)
H480.767784−0.1216520.6088460.040*
C490.8292 (3)−0.0259 (3)0.53334 (17)0.0295 (8)
H490.901284−0.0468030.5403920.035*
C500.8047 (3)0.0487 (2)0.48251 (15)0.0220 (7)
C510.9211 (3)0.0880 (3)0.38313 (16)0.0271 (7)
C520.9964 (3)0.1547 (3)0.34652 (16)0.0281 (7)
C530.9861 (3)0.2524 (3)0.35526 (19)0.0372 (9)
H530.9307510.2797640.3861330.045*
C541.0574 (4)0.3092 (3)0.3185 (2)0.0468 (11)
H541.0523420.3764910.3236150.056*
C551.1358 (4)0.2677 (4)0.2743 (2)0.0497 (11)
H551.1849560.3077130.2495150.060*
C561.0774 (3)0.1195 (3)0.3000 (2)0.0394 (9)
H561.0834880.0529720.2933500.047*
C570.5139 (3)0.0806 (3)0.20926 (15)0.0227 (7)
C580.4059 (3)0.0830 (3)0.20982 (18)0.0323 (8)
H580.3501840.1319340.2286570.039*
C590.3788 (4)0.0159 (3)0.1837 (2)0.0454 (11)
H590.3050900.0196620.1840080.054*
C600.4582 (4)−0.0563 (3)0.1571 (2)0.0491 (12)
H600.439354−0.1025090.1390850.059*
C610.5651 (3)−0.0620 (3)0.1565 (2)0.0395 (9)
H610.619824−0.1123710.1382690.047*
C620.5932 (3)0.0056 (3)0.18252 (16)0.0261 (7)
C630.7756 (3)−0.0872 (3)0.19658 (16)0.0278 (7)
C640.8912 (3)−0.0806 (3)0.18496 (17)0.0305 (8)
C650.9233 (4)−0.0037 (4)0.1989 (3)0.0552 (13)
H650.8694740.0478610.2165600.066*
C661.1009 (4)−0.0725 (5)0.1643 (3)0.0619 (14)
H661.175063−0.0714130.1580300.074*
C671.0758 (4)−0.1478 (5)0.1485 (3)0.0658 (15)
H671.131010−0.1972430.1298460.079*
C680.9698 (4)−0.1544 (4)0.1591 (2)0.0540 (12)
H680.951208−0.2090120.1487680.065*
C690.8132 (3)0.2408 (3)0.2457 (2)0.0403 (10)
H690.8087800.1768300.2725550.048*
C700.7735 (3)0.3964 (3)0.2004 (2)0.0417 (10)
H700.7354390.4649500.1883770.050*
C710.9001 (3)0.2596 (4)0.20197 (19)0.0398 (10)
H710.9663790.2119190.1931410.048*
C720.9429 (5)0.4088 (5)0.1217 (3)0.0746 (18)
H72A1.0090030.4105230.1341060.112*
H72B0.9031720.4789480.1084130.112*
H72C0.9617260.3721370.0875570.112*
C730.3874 (3)0.4273 (3)0.38259 (16)0.0276 (7)
H730.4193270.4772040.3886360.033*
C740.2703 (3)0.3381 (3)0.39007 (19)0.0349 (9)
H740.2066250.3121650.4012080.042*
C750.3623 (3)0.3042 (3)0.35137 (19)0.0345 (9)
H750.3738140.2494360.3306180.041*
C760.2109 (3)0.4733 (3)0.4539 (2)0.0395 (10)
H76A0.2185050.4365760.4958920.059*
H76B0.1370790.4808150.4481950.059*
H76C0.2260700.5412110.4472380.059*
O50.2857 (6)0.6768 (6)0.3207 (3)0.156 (3)
C770.3330 (7)0.8184 (6)0.3382 (4)0.127 (3)
H77A0.4056750.8255300.3148170.152*
H77B0.3119780.8578990.3716260.152*
C780.3289 (5)0.7083 (6)0.3629 (3)0.089 (2)
H78A0.4022030.6660840.3664240.107*
H78B0.2823350.7005120.4042580.107*
C790.2486 (7)0.8521 (7)0.2954 (4)0.114 (3)
H79A0.1748220.8741220.3185320.137*
H79B0.2654530.9086340.2609500.137*
C800.2597 (6)0.7592 (7)0.2731 (4)0.118 (3)
H80A0.1912630.7587520.2619460.141*
H80B0.3175190.7551710.2360830.141*
O60.8138 (5)0.8462 (5)0.0574 (3)0.0590 (17)0.5
C810.7780 (13)0.9096 (11)0.0030 (6)0.106 (4)0.5
H81A0.8331780.946314−0.0234550.127*0.5
H81B0.7093780.9595250.0128890.127*0.5
C820.7627 (19)0.8267 (13)−0.0271 (10)0.151 (6)0.5
H82A0.6853740.839013−0.0291430.181*0.5
H82B0.8039460.833595−0.0698770.181*0.5
C830.7993 (14)0.7171 (13)0.0077 (7)0.116 (5)0.5
H83A0.7471060.6744270.0121480.139*0.5
H83B0.8721000.682948−0.0113470.139*0.5
C840.7989 (10)0.7451 (8)0.0686 (6)0.077 (3)0.5
H84A0.7292970.7400920.0968770.093*0.5
H84B0.8575360.6966970.0884290.093*0.5
N170.0059 (3)0.7796 (3)0.40172 (16)0.0375 (8)
N180.0525 (3)0.7857 (3)0.48807 (17)0.0389 (8)
C850.0185 (3)0.6969 (3)0.4962 (2)0.0410 (9)
H850.0155280.6462190.5329830.049*
C860.0447 (4)0.8320 (3)0.4308 (2)0.0440 (10)
H860.0643410.8954360.4119550.053*
C87−0.0108 (3)0.6926 (3)0.4428 (2)0.0406 (9)
H87−0.0373610.6396110.4360740.049*
C88−0.0119 (4)0.8112 (4)0.3383 (2)0.0458 (10)
H88A0.0122330.8749040.3191610.069*
H88B−0.0889570.8223190.3380550.069*
H88C0.0291660.7576430.3151630.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0180 (2)0.0162 (2)0.0160 (2)−0.00469 (17)−0.00201 (17)−0.00551 (16)
O10.056 (2)0.069 (2)0.0226 (15)0.0063 (17)0.0020 (13)0.0037 (14)
O20.0355 (14)0.0349 (14)0.0275 (14)−0.0039 (11)−0.0031 (11)−0.0037 (11)
O30.0314 (14)0.0386 (15)0.0373 (15)−0.0101 (12)−0.0031 (11)−0.0139 (12)
O40.0412 (16)0.0273 (14)0.0465 (17)−0.0083 (12)−0.0096 (13)0.0002 (12)
N10.0220 (13)0.0189 (13)0.0168 (13)−0.0050 (11)−0.0011 (10)−0.0049 (10)
N20.0203 (13)0.0206 (13)0.0164 (13)−0.0064 (11)−0.0020 (10)−0.0053 (10)
N30.0159 (12)0.0136 (12)0.0200 (13)−0.0032 (10)−0.0023 (10)−0.0041 (10)
N40.0173 (12)0.0185 (13)0.0187 (13)−0.0037 (10)−0.0034 (10)−0.0067 (10)
N50.048 (2)0.0327 (17)0.0169 (14)−0.0007 (15)−0.0039 (13)−0.0024 (12)
N60.0261 (15)0.0251 (14)0.0198 (14)−0.0081 (12)0.0010 (11)−0.0061 (11)
N70.0206 (14)0.0259 (15)0.0279 (15)−0.0064 (11)−0.0076 (11)−0.0047 (12)
N80.0301 (15)0.0219 (14)0.0279 (15)−0.0057 (12)−0.0035 (12)−0.0095 (12)
N90.0373 (19)0.0370 (19)0.044 (2)−0.0062 (15)0.0024 (15)−0.0121 (16)
N100.048 (2)0.080 (3)0.0317 (19)−0.013 (2)0.0092 (16)−0.0215 (19)
N110.0282 (18)0.061 (3)0.051 (2)−0.0142 (17)0.0067 (16)−0.0089 (19)
N120.052 (3)0.093 (4)0.088 (3)−0.024 (2)−0.010 (2)−0.050 (3)
N130.0223 (14)0.0247 (14)0.0199 (13)−0.0063 (11)−0.0009 (11)−0.0082 (11)
N140.0368 (19)0.057 (2)0.046 (2)−0.0167 (17)0.0125 (16)−0.0212 (18)
N150.0214 (13)0.0184 (13)0.0162 (13)−0.0035 (10)−0.0049 (10)−0.0039 (10)
N160.0201 (14)0.0323 (16)0.0285 (15)−0.0046 (12)0.0004 (12)−0.0140 (13)
C10.0203 (15)0.0234 (16)0.0201 (16)−0.0045 (13)−0.0038 (12)−0.0085 (13)
C20.0308 (18)0.0295 (18)0.0227 (17)−0.0059 (14)−0.0079 (14)−0.0098 (14)
C30.0357 (19)0.0287 (18)0.0206 (17)−0.0046 (15)−0.0111 (14)−0.0063 (14)
C40.0277 (17)0.0220 (16)0.0187 (15)−0.0021 (13)−0.0054 (13)−0.0063 (13)
C50.0273 (17)0.0231 (16)0.0166 (15)−0.0024 (13)−0.0036 (13)−0.0041 (12)
C60.0273 (17)0.0200 (16)0.0190 (15)−0.0052 (13)−0.0008 (13)−0.0054 (12)
C70.043 (2)0.0224 (17)0.0224 (17)−0.0102 (15)−0.0090 (15)0.0013 (13)
C80.039 (2)0.0216 (17)0.0270 (18)−0.0108 (15)−0.0099 (15)−0.0026 (14)
C90.0229 (16)0.0168 (15)0.0198 (15)−0.0055 (12)−0.0026 (12)−0.0051 (12)
C100.0198 (15)0.0201 (15)0.0184 (15)−0.0070 (12)−0.0003 (12)−0.0075 (12)
C110.0160 (14)0.0192 (15)0.0212 (15)−0.0052 (12)−0.0013 (12)−0.0082 (12)
C120.0224 (16)0.0213 (16)0.0248 (16)−0.0057 (13)−0.0066 (13)−0.0087 (13)
C130.0234 (16)0.0228 (16)0.0190 (15)−0.0042 (13)−0.0084 (12)−0.0050 (12)
C140.0143 (14)0.0182 (15)0.0210 (15)−0.0045 (12)−0.0028 (12)−0.0059 (12)
C150.0131 (14)0.0178 (15)0.0200 (15)−0.0040 (11)−0.0028 (11)−0.0047 (12)
C160.0169 (14)0.0174 (15)0.0190 (15)−0.0037 (12)−0.0021 (12)−0.0049 (12)
C170.0254 (17)0.0179 (15)0.0244 (16)−0.0050 (13)−0.0059 (13)−0.0045 (12)
C180.0262 (17)0.0173 (15)0.0245 (17)−0.0046 (13)−0.0047 (13)−0.0068 (13)
C190.0187 (15)0.0176 (15)0.0224 (16)−0.0060 (12)−0.0020 (12)−0.0072 (12)
C200.0179 (15)0.0224 (16)0.0218 (16)−0.0063 (12)−0.0009 (12)−0.0094 (13)
C210.0359 (19)0.0244 (17)0.0192 (16)−0.0068 (15)−0.0089 (14)−0.0031 (13)
C220.038 (2)0.0289 (19)0.0282 (19)−0.0054 (16)−0.0089 (16)−0.0062 (15)
C230.050 (3)0.031 (2)0.040 (2)−0.0009 (18)−0.0170 (19)−0.0036 (17)
C240.059 (3)0.041 (2)0.028 (2)−0.007 (2)−0.0197 (19)0.0025 (17)
C250.057 (3)0.037 (2)0.0214 (18)−0.0043 (19)−0.0091 (17)−0.0032 (16)
C260.040 (2)0.0295 (19)0.0235 (18)−0.0046 (16)−0.0102 (15)−0.0053 (14)
C270.035 (2)0.047 (2)0.0195 (18)−0.0057 (17)−0.0052 (15)−0.0032 (16)
C280.0316 (19)0.043 (2)0.0243 (18)−0.0055 (17)−0.0026 (15)−0.0110 (16)
C290.0290 (19)0.036 (2)0.032 (2)−0.0069 (16)0.0004 (15)−0.0109 (16)
C300.049 (3)0.043 (3)0.051 (3)0.004 (2)0.000 (2)−0.011 (2)
C310.048 (3)0.063 (3)0.045 (3)0.011 (2)0.013 (2)−0.011 (2)
C320.040 (2)0.056 (3)0.031 (2)−0.003 (2)0.0031 (18)−0.0045 (19)
C330.0214 (15)0.0158 (14)0.0212 (16)−0.0038 (12)−0.0069 (12)−0.0041 (12)
C340.0232 (16)0.0224 (16)0.0249 (17)−0.0083 (13)−0.0003 (13)−0.0056 (13)
C350.0278 (18)0.0290 (18)0.0246 (17)−0.0047 (14)0.0038 (14)−0.0129 (14)
C360.035 (2)0.0229 (17)0.0340 (19)−0.0062 (15)−0.0021 (15)−0.0166 (15)
C370.0279 (18)0.0213 (17)0.0357 (19)−0.0131 (14)0.0000 (15)−0.0092 (14)
C380.0251 (16)0.0180 (15)0.0202 (16)−0.0059 (13)−0.0008 (13)−0.0052 (12)
C390.0284 (18)0.0213 (16)0.0263 (18)−0.0085 (14)0.0001 (14)−0.0089 (14)
C400.0317 (19)0.0251 (17)0.0274 (18)−0.0087 (15)0.0070 (15)−0.0094 (14)
C410.033 (2)0.056 (3)0.033 (2)−0.0119 (19)0.0047 (17)−0.0149 (19)
C420.040 (2)0.062 (3)0.042 (2)−0.011 (2)0.0138 (19)−0.019 (2)
C430.032 (2)0.044 (2)0.051 (3)−0.0132 (18)0.0075 (18)−0.013 (2)
C440.032 (2)0.033 (2)0.038 (2)−0.0111 (16)0.0014 (16)−0.0095 (16)
C450.0214 (15)0.0160 (15)0.0233 (16)−0.0031 (12)−0.0068 (13)−0.0071 (12)
C460.0234 (16)0.0246 (17)0.0280 (18)−0.0060 (13)−0.0053 (14)−0.0064 (14)
C470.0317 (19)0.0297 (19)0.0283 (18)−0.0110 (15)−0.0055 (15)−0.0002 (15)
C480.039 (2)0.0307 (19)0.0286 (19)−0.0079 (16)−0.0127 (16)0.0057 (15)
C490.0234 (17)0.0313 (19)0.0326 (19)−0.0005 (14)−0.0137 (15)−0.0020 (15)
C500.0222 (16)0.0215 (16)0.0241 (16)−0.0033 (13)−0.0067 (13)−0.0072 (13)
C510.0187 (16)0.0289 (18)0.0311 (19)0.0008 (14)−0.0064 (14)−0.0058 (15)
C520.0217 (17)0.0317 (19)0.0294 (18)−0.0045 (14)−0.0076 (14)−0.0021 (15)
C530.034 (2)0.032 (2)0.039 (2)−0.0035 (16)−0.0032 (17)−0.0026 (17)
C540.046 (3)0.033 (2)0.057 (3)−0.0117 (19)−0.008 (2)−0.001 (2)
C550.037 (2)0.052 (3)0.057 (3)−0.020 (2)−0.006 (2)0.004 (2)
C560.028 (2)0.043 (2)0.046 (2)−0.0094 (17)0.0012 (17)−0.0118 (19)
C570.0264 (17)0.0235 (16)0.0219 (16)−0.0067 (13)−0.0072 (13)−0.0074 (13)
C580.0279 (19)0.0314 (19)0.043 (2)−0.0070 (15)−0.0106 (16)−0.0135 (17)
C590.038 (2)0.043 (2)0.069 (3)−0.0109 (19)−0.023 (2)−0.022 (2)
C600.054 (3)0.040 (2)0.072 (3)−0.012 (2)−0.028 (2)−0.027 (2)
C610.045 (2)0.032 (2)0.049 (2)−0.0039 (17)−0.0126 (19)−0.0224 (18)
C620.0293 (18)0.0236 (17)0.0278 (18)−0.0047 (14)−0.0076 (14)−0.0085 (14)
C630.0326 (19)0.0271 (18)0.0237 (17)−0.0046 (15)−0.0040 (14)−0.0082 (14)
C640.0304 (19)0.0310 (19)0.0308 (19)−0.0038 (15)−0.0060 (15)−0.0106 (15)
C650.040 (2)0.064 (3)0.072 (3)−0.011 (2)−0.006 (2)−0.039 (3)
C660.030 (2)0.082 (4)0.080 (4)−0.012 (2)−0.009 (2)−0.029 (3)
C670.031 (2)0.077 (4)0.089 (4)−0.008 (2)0.011 (2)−0.043 (3)
C680.042 (3)0.053 (3)0.070 (3)−0.013 (2)0.002 (2)−0.025 (2)
C690.028 (2)0.037 (2)0.048 (2)0.0004 (17)0.0011 (17)−0.0123 (18)
C700.040 (2)0.039 (2)0.043 (2)−0.0125 (18)0.0078 (18)−0.0118 (18)
C710.0188 (18)0.055 (3)0.043 (2)−0.0009 (17)0.0038 (16)−0.022 (2)
C720.067 (4)0.088 (4)0.070 (4)−0.040 (3)0.025 (3)−0.028 (3)
C730.0258 (17)0.0298 (18)0.0315 (19)−0.0096 (14)0.0007 (14)−0.0155 (15)
C740.0251 (18)0.042 (2)0.044 (2)−0.0172 (16)0.0057 (16)−0.0208 (18)
C750.0289 (19)0.039 (2)0.043 (2)−0.0168 (16)0.0044 (16)−0.0226 (18)
C760.0265 (19)0.050 (2)0.044 (2)−0.0068 (17)0.0064 (17)−0.028 (2)
O50.155 (5)0.196 (6)0.125 (5)−0.039 (5)−0.060 (4)−0.013 (4)
C770.108 (5)0.143 (6)0.083 (5)−0.013 (5)0.008 (4)0.021 (4)
C780.065 (4)0.115 (5)0.089 (4)−0.018 (3)−0.033 (3)−0.006 (4)
C790.137 (6)0.137 (5)0.086 (5)−0.092 (5)−0.049 (4)0.042 (4)
C800.072 (4)0.155 (6)0.084 (4)0.024 (4)−0.009 (3)−0.008 (4)
O60.050 (4)0.061 (4)0.053 (4)0.002 (3)0.003 (3)−0.015 (3)
C810.098 (8)0.118 (7)0.087 (7)−0.027 (6)−0.021 (6)0.013 (5)
C820.158 (11)0.185 (9)0.138 (9)−0.064 (8)−0.062 (8)−0.021 (7)
C830.101 (8)0.146 (8)0.134 (8)−0.060 (7)−0.031 (7)−0.044 (6)
C840.064 (6)0.074 (5)0.085 (6)−0.015 (5)0.006 (5)−0.019 (5)
N170.0352 (18)0.0389 (19)0.0436 (19)−0.0110 (15)−0.0109 (15)−0.0113 (15)
N180.0371 (18)0.0350 (18)0.051 (2)−0.0074 (15)−0.0163 (16)−0.0121 (16)
C850.037 (2)0.040 (2)0.050 (3)−0.0112 (18)−0.0079 (19)−0.0130 (19)
C860.047 (2)0.033 (2)0.061 (3)−0.0095 (18)−0.027 (2)−0.009 (2)
C870.045 (2)0.037 (2)0.046 (2)−0.0164 (18)−0.0099 (19)−0.0099 (18)
C880.051 (3)0.051 (3)0.043 (2)−0.021 (2)−0.010 (2)−0.011 (2)
Geometric parameters (Å, º) top
Fe1—N11.982 (3)C35—H350.9500
Fe1—N31.985 (3)C36—C371.379 (5)
Fe1—N41.993 (3)C36—H360.9500
Fe1—N151.993 (3)C37—C381.393 (5)
Fe1—N22.001 (3)C37—H370.9500
Fe1—N132.004 (3)C39—C401.503 (5)
O1—C271.225 (5)C40—C411.368 (6)
O2—C391.224 (4)C40—C441.387 (5)
O3—C511.228 (4)C41—H410.9500
O4—C631.228 (4)C42—C431.366 (7)
N1—C41.379 (4)C42—H420.9500
N1—C11.384 (4)C43—C441.381 (5)
N2—C61.374 (4)C43—H430.9500
N2—C91.377 (4)C44—H440.9500
N3—C111.375 (4)C45—C461.394 (5)
N3—C141.376 (4)C45—C501.396 (4)
N4—C161.366 (4)C46—C471.385 (5)
N4—C191.386 (4)C46—H460.9500
N5—C271.348 (5)C47—C481.392 (5)
N5—C261.419 (5)C47—H470.9500
N5—H50.8800C48—C491.382 (5)
N6—C391.349 (4)C48—H480.9500
N6—C381.429 (4)C49—C501.383 (5)
N6—H60.8800C49—H490.9500
N7—C511.348 (5)C51—C521.494 (5)
N7—C501.422 (4)C52—C531.382 (5)
N7—H70.8800C52—C561.386 (5)
N8—C631.348 (5)C53—C541.373 (6)
N8—C621.433 (5)C53—H530.9500
N8—H80.8800C54—C551.367 (7)
N9—C291.336 (5)C54—H540.9500
N9—C301.338 (5)C55—H550.9500
N10—C421.339 (6)C56—H560.9500
N10—C411.352 (5)C57—C621.398 (5)
N11—C561.336 (5)C57—C581.402 (5)
N11—C551.336 (6)C58—C591.377 (5)
N12—C661.344 (7)C58—H580.9500
N12—C651.345 (6)C59—C601.372 (6)
N13—C701.328 (5)C59—H590.9500
N13—C691.358 (5)C60—C611.377 (6)
N14—C711.323 (6)C60—H600.9500
N14—C701.355 (5)C61—C621.389 (5)
N14—C721.458 (6)C61—H610.9500
N15—C731.314 (4)C63—C641.497 (5)
N15—C751.368 (4)C64—C651.372 (6)
N16—C731.345 (4)C64—C681.374 (6)
N16—C741.349 (5)C65—H650.9500
N16—C761.457 (4)C66—C671.323 (7)
C1—C201.392 (5)C66—H660.9500
C1—C21.439 (5)C67—C681.373 (7)
C2—C31.344 (5)C67—H670.9500
C2—H20.9500C68—H680.9500
C3—C41.436 (5)C69—C711.357 (6)
C3—H30.9500C69—H690.9500
C4—C51.400 (5)C70—H700.9500
C5—C61.392 (5)C71—H710.9500
C5—C211.494 (4)C72—H72A0.9800
C6—C71.439 (5)C72—H72B0.9800
C7—C81.344 (5)C72—H72C0.9800
C7—H7A0.9500C73—H730.9500
C8—C91.441 (5)C74—C751.356 (5)
C8—H8A0.9500C74—H740.9500
C9—C101.391 (4)C75—H750.9500
C10—C111.395 (4)C76—H76A0.9800
C10—C331.502 (4)C76—H76B0.9800
C11—C121.437 (4)C76—H76C0.9800
C12—C131.339 (5)O5—C801.394 (7)
C12—H120.9500O5—C781.427 (7)
C13—C141.446 (4)C77—C781.498 (8)
C13—H130.9500C77—C791.548 (8)
C14—C151.389 (4)C77—H77A0.9900
C15—C161.393 (4)C77—H77B0.9900
C15—C451.497 (4)C78—H78A0.9900
C16—C171.444 (4)C78—H78B0.9900
C17—C181.341 (5)C79—C801.457 (8)
C17—H170.9500C79—H79A0.9900
C18—C191.447 (4)C79—H79B0.9900
C18—H180.9500C80—H80A0.9900
C19—C201.390 (5)C80—H80B0.9900
C20—C571.494 (4)O6—C841.417 (8)
C21—C221.386 (5)O6—C811.428 (9)
C21—C261.408 (5)C81—C821.552 (10)
C22—C231.389 (5)C81—H81A0.9900
C22—H220.9500C81—H81B0.9900
C23—C241.384 (6)C82—C831.533 (10)
C23—H230.9500C82—H82A0.9900
C24—C251.387 (6)C82—H82B0.9900
C24—H240.9500C83—C841.528 (9)
C25—C261.390 (5)C83—H83A0.9900
C25—H250.9500C83—H83B0.9900
C27—C281.500 (6)C84—H84A0.9900
C28—C291.392 (5)C84—H84B0.9900
C28—C321.397 (5)N17—C861.350 (5)
C29—H290.9500N17—C871.363 (5)
C30—C311.382 (7)N17—C881.456 (5)
C30—H300.9500N18—C861.317 (6)
C31—C321.377 (7)N18—C851.373 (5)
C31—H310.9500C85—C871.377 (6)
C32—H320.9500C85—H850.9500
C33—C381.390 (4)C86—H860.9500
C33—C341.400 (4)C87—H870.9500
C34—C351.385 (5)C88—H88A0.9800
C34—H340.9500C88—H88B0.9800
C35—C361.372 (5)C88—H88C0.9800
N1—Fe1—N3178.48 (11)N10—C42—H42118.2
N1—Fe1—N489.13 (11)C43—C42—H42118.2
N3—Fe1—N490.55 (10)C42—C43—C44119.2 (4)
N1—Fe1—N1588.61 (11)C42—C43—H43120.4
N3—Fe1—N1589.91 (10)C44—C43—H43120.4
N4—Fe1—N1589.74 (10)C43—C44—C40118.5 (4)
N1—Fe1—N290.97 (11)C43—C44—H44120.8
N3—Fe1—N289.38 (10)C40—C44—H44120.8
N4—Fe1—N2178.69 (11)C46—C45—C50118.0 (3)
N15—Fe1—N291.57 (11)C46—C45—C15119.9 (3)
N1—Fe1—N1390.73 (11)C50—C45—C15122.1 (3)
N3—Fe1—N1390.75 (11)C47—C46—C45121.6 (3)
N4—Fe1—N1390.23 (11)C47—C46—H46119.2
N15—Fe1—N13179.34 (11)C45—C46—H46119.2
N2—Fe1—N1388.47 (11)C46—C47—C48119.5 (3)
C4—N1—C1105.3 (3)C46—C47—H47120.2
C4—N1—Fe1126.2 (2)C48—C47—H47120.2
C1—N1—Fe1128.4 (2)C49—C48—C47119.4 (3)
C6—N2—C9105.1 (3)C49—C48—H48120.3
C6—N2—Fe1126.5 (2)C47—C48—H48120.3
C9—N2—Fe1128.0 (2)C48—C49—C50121.0 (3)
C11—N3—C14105.2 (2)C48—C49—H49119.5
C11—N3—Fe1127.9 (2)C50—C49—H49119.5
C14—N3—Fe1126.8 (2)C49—C50—C45120.5 (3)
C16—N4—C19105.0 (3)C49—C50—N7119.4 (3)
C16—N4—Fe1127.0 (2)C45—C50—N7120.1 (3)
C19—N4—Fe1128.0 (2)O3—C51—N7124.2 (3)
C27—N5—C26129.9 (3)O3—C51—C52120.6 (3)
C27—N5—H5115.1N7—C51—C52115.2 (3)
C26—N5—H5115.1C53—C52—C56118.1 (4)
C39—N6—C38119.9 (3)C53—C52—C51122.7 (3)
C39—N6—H6120.1C56—C52—C51119.1 (3)
C38—N6—H6120.1C54—C53—C52118.7 (4)
C51—N7—C50122.9 (3)C54—C53—H53120.6
C51—N7—H7118.5C52—C53—H53120.6
C50—N7—H7118.5C55—C54—C53119.1 (4)
C63—N8—C62122.7 (3)C55—C54—H54120.4
C63—N8—H8118.7C53—C54—H54120.4
C62—N8—H8118.7N11—C55—C54123.8 (4)
C29—N9—C30117.0 (4)N11—C55—H55118.1
C42—N10—C41116.4 (4)C54—C55—H55118.1
C56—N11—C55116.6 (4)N11—C56—C52123.6 (4)
C66—N12—C65116.5 (4)N11—C56—H56118.2
C70—N13—C69104.7 (3)C52—C56—H56118.2
C70—N13—Fe1127.5 (3)C62—C57—C58117.4 (3)
C69—N13—Fe1127.7 (3)C62—C57—C20124.2 (3)
C71—N14—C70106.9 (3)C58—C57—C20118.4 (3)
C71—N14—C72126.6 (4)C59—C58—C57121.5 (4)
C70—N14—C72126.4 (5)C59—C58—H58119.3
C73—N15—C75105.1 (3)C57—C58—H58119.3
C73—N15—Fe1128.0 (2)C60—C59—C58120.0 (4)
C75—N15—Fe1126.9 (2)C60—C59—H59120.0
C73—N16—C74107.1 (3)C58—C59—H59120.0
C73—N16—C76127.1 (3)C59—C60—C61120.2 (4)
C74—N16—C76125.8 (3)C59—C60—H60119.9
N1—C1—C20125.2 (3)C61—C60—H60119.9
N1—C1—C2109.7 (3)C60—C61—C62120.2 (4)
C20—C1—C2125.0 (3)C60—C61—H61119.9
C3—C2—C1107.6 (3)C62—C61—H61119.9
C3—C2—H2126.2C61—C62—C57120.7 (3)
C1—C2—H2126.2C61—C62—N8119.1 (3)
C2—C3—C4106.9 (3)C57—C62—N8120.1 (3)
C2—C3—H3126.5O4—C63—N8124.0 (3)
C4—C3—H3126.5O4—C63—C64120.1 (3)
N1—C4—C5125.9 (3)N8—C63—C64115.8 (3)
N1—C4—C3110.5 (3)C65—C64—C68117.8 (4)
C5—C4—C3123.4 (3)C65—C64—C63123.1 (3)
C6—C5—C4123.8 (3)C68—C64—C63119.1 (4)
C6—C5—C21118.4 (3)N12—C65—C64123.3 (4)
C4—C5—C21117.5 (3)N12—C65—H65118.3
N2—C6—C5125.4 (3)C64—C65—H65118.3
N2—C6—C7110.4 (3)C67—C66—N12123.5 (5)
C5—C6—C7124.1 (3)C67—C66—H66118.3
C8—C7—C6107.1 (3)N12—C66—H66118.3
C8—C7—H7A126.5C66—C67—C68120.0 (5)
C6—C7—H7A126.5C66—C67—H67120.0
C7—C8—C9106.8 (3)C68—C67—H67120.0
C7—C8—H8A126.6C67—C68—C64118.8 (5)
C9—C8—H8A126.6C67—C68—H68120.6
N2—C9—C10125.0 (3)C64—C68—H68120.6
N2—C9—C8110.5 (3)C71—C69—N13109.7 (4)
C10—C9—C8124.5 (3)C71—C69—H69125.2
C9—C10—C11123.5 (3)N13—C69—H69125.2
C9—C10—C33119.1 (3)N13—C70—N14111.1 (4)
C11—C10—C33117.2 (3)N13—C70—H70124.4
N3—C11—C10125.9 (3)N14—C70—H70124.4
N3—C11—C12110.2 (3)N14—C71—C69107.5 (3)
C10—C11—C12123.9 (3)N14—C71—H71126.2
C13—C12—C11107.6 (3)C69—C71—H71126.2
C13—C12—H12126.2N14—C72—H72A109.5
C11—C12—H12126.2N14—C72—H72B109.5
C12—C13—C14106.6 (3)H72A—C72—H72B109.5
C12—C13—H13126.7N14—C72—H72C109.5
C14—C13—H13126.7H72A—C72—H72C109.5
N3—C14—C15125.9 (3)H72B—C72—H72C109.5
N3—C14—C13110.4 (3)N15—C73—N16111.7 (3)
C15—C14—C13123.8 (3)N15—C73—H73124.2
C14—C15—C16123.8 (3)N16—C73—H73124.2
C14—C15—C45118.7 (3)N16—C74—C75106.5 (3)
C16—C15—C45117.5 (3)N16—C74—H74126.7
N4—C16—C15125.8 (3)C75—C74—H74126.7
N4—C16—C17110.9 (3)C74—C75—N15109.7 (3)
C15—C16—C17123.3 (3)C74—C75—H75125.2
C18—C17—C16107.0 (3)N15—C75—H75125.2
C18—C17—H17126.5N16—C76—H76A109.5
C16—C17—H17126.5N16—C76—H76B109.5
C17—C18—C19106.8 (3)H76A—C76—H76B109.5
C17—C18—H18126.6N16—C76—H76C109.5
C19—C18—H18126.6H76A—C76—H76C109.5
N4—C19—C20125.4 (3)H76B—C76—H76C109.5
N4—C19—C18110.2 (3)C80—O5—C78109.7 (7)
C20—C19—C18124.3 (3)C78—C77—C79101.3 (7)
C19—C20—C1123.3 (3)C78—C77—H77A111.5
C19—C20—C57119.0 (3)C79—C77—H77A111.5
C1—C20—C57117.6 (3)C78—C77—H77B111.5
C22—C21—C26118.5 (3)C79—C77—H77B111.5
C22—C21—C5121.9 (3)H77A—C77—H77B109.3
C26—C21—C5119.5 (3)O5—C78—C77107.3 (7)
C21—C22—C23121.5 (4)O5—C78—H78A110.3
C21—C22—H22119.3C77—C78—H78A110.3
C23—C22—H22119.3O5—C78—H78B110.3
C24—C23—C22119.0 (4)C77—C78—H78B110.3
C24—C23—H23120.5H78A—C78—H78B108.5
C22—C23—H23120.5C80—C79—C77102.5 (8)
C23—C24—C25121.1 (4)C80—C79—H79A111.3
C23—C24—H24119.5C77—C79—H79A111.3
C25—C24—H24119.5C80—C79—H79B111.3
C24—C25—C26119.5 (4)C77—C79—H79B111.3
C24—C25—H25120.3H79A—C79—H79B109.2
C26—C25—H25120.3O5—C80—C79107.1 (7)
C25—C26—C21120.4 (3)O5—C80—H80A110.3
C25—C26—N5122.6 (3)C79—C80—H80A110.3
C21—C26—N5117.0 (3)O5—C80—H80B110.3
O1—C27—N5123.6 (4)C79—C80—H80B110.3
O1—C27—C28120.6 (4)H80A—C80—H80B108.5
N5—C27—C28115.7 (3)C84—O6—C81113.4 (10)
C29—C28—C32117.3 (4)O6—C81—C8299.7 (11)
C29—C28—C27124.8 (3)O6—C81—H81A111.8
C32—C28—C27117.8 (4)C82—C81—H81A111.8
N9—C29—C28124.3 (4)O6—C81—H81B111.8
N9—C29—H29117.9C82—C81—H81B111.8
C28—C29—H29117.9H81A—C81—H81B109.6
N9—C30—C31123.2 (4)C83—C82—C81113.6 (13)
N9—C30—H30118.4C83—C82—H82A108.9
C31—C30—H30118.4C81—C82—H82A108.9
C32—C31—C30119.3 (4)C83—C82—H82B108.9
C32—C31—H31120.4C81—C82—H82B108.9
C30—C31—H31120.4H82A—C82—H82B107.7
C31—C32—C28118.9 (4)C84—C83—C8296.6 (13)
C31—C32—H32120.6C84—C83—H83A112.4
C28—C32—H32120.6C82—C83—H83A112.4
C38—C33—C34117.5 (3)C84—C83—H83B112.4
C38—C33—C10124.6 (3)C82—C83—H83B112.4
C34—C33—C10117.9 (3)H83A—C83—H83B110.0
C35—C34—C33121.7 (3)O6—C84—C83109.7 (10)
C35—C34—H34119.1O6—C84—H84A109.7
C33—C34—H34119.1C83—C84—H84A109.7
C36—C35—C34119.8 (3)O6—C84—H84B109.7
C36—C35—H35120.1C83—C84—H84B109.7
C34—C35—H35120.1H84A—C84—H84B108.2
C35—C36—C37119.7 (3)C86—N17—C87106.5 (4)
C35—C36—H36120.1C86—N17—C88125.6 (4)
C37—C36—H36120.1C87—N17—C88127.9 (3)
C36—C37—C38120.7 (3)C86—N18—C85104.8 (3)
C36—C37—H37119.6N18—C85—C87109.6 (4)
C38—C37—H37119.6N18—C85—H85125.2
C33—C38—C37120.5 (3)C87—C85—H85125.2
C33—C38—N6121.5 (3)N18—C86—N17112.7 (4)
C37—C38—N6117.9 (3)N18—C86—H86123.6
O2—C39—N6123.6 (3)N17—C86—H86123.6
O2—C39—C40120.5 (3)N17—C87—C85106.3 (4)
N6—C39—C40115.9 (3)N17—C87—H87126.9
C41—C40—C44118.5 (3)C85—C87—H87126.9
C41—C40—C39123.0 (3)N17—C88—H88A109.5
C44—C40—C39118.5 (3)N17—C88—H88B109.5
N10—C41—C40123.8 (4)H88A—C88—H88B109.5
N10—C41—H41118.1N17—C88—H88C109.5
C40—C41—H41118.1H88A—C88—H88C109.5
N10—C42—C43123.7 (4)H88B—C88—H88C109.5
C4—N1—C1—C20175.1 (3)C34—C35—C36—C37−0.3 (6)
Fe1—N1—C1—C20−8.4 (5)C35—C36—C37—C38−1.0 (6)
C4—N1—C1—C2−1.7 (4)C34—C33—C38—C37−1.5 (5)
Fe1—N1—C1—C2174.8 (2)C10—C33—C38—C37178.4 (3)
N1—C1—C2—C30.4 (4)C34—C33—C38—N6176.5 (3)
C20—C1—C2—C3−176.5 (3)C10—C33—C38—N6−3.6 (5)
C1—C2—C3—C41.1 (4)C36—C37—C38—C332.0 (5)
C1—N1—C4—C5−172.4 (3)C36—C37—C38—N6−176.1 (3)
Fe1—N1—C4—C511.0 (5)C39—N6—C38—C33−92.4 (4)
C1—N1—C4—C32.4 (4)C39—N6—C38—C3785.7 (4)
Fe1—N1—C4—C3−174.2 (2)C38—N6—C39—O24.1 (5)
C2—C3—C4—N1−2.3 (4)C38—N6—C39—C40−175.1 (3)
C2—C3—C4—C5172.7 (3)O2—C39—C40—C41146.9 (4)
N1—C4—C5—C6−9.3 (5)N6—C39—C40—C41−33.8 (5)
C3—C4—C5—C6176.5 (3)O2—C39—C40—C44−29.8 (5)
N1—C4—C5—C21164.0 (3)N6—C39—C40—C44149.4 (3)
C3—C4—C5—C21−10.1 (5)C42—N10—C41—C40−0.5 (7)
C9—N2—C6—C5−176.7 (3)C44—C40—C41—N100.5 (6)
Fe1—N2—C6—C59.9 (5)C39—C40—C41—N10−176.3 (4)
C9—N2—C6—C72.5 (4)C41—N10—C42—C430.3 (7)
Fe1—N2—C6—C7−170.9 (2)N10—C42—C43—C44−0.1 (7)
C4—C5—C6—N2−1.8 (5)C42—C43—C44—C400.0 (6)
C21—C5—C6—N2−175.1 (3)C41—C40—C44—C43−0.2 (6)
C4—C5—C6—C7179.1 (3)C39—C40—C44—C43176.7 (3)
C21—C5—C6—C75.8 (5)C14—C15—C45—C46110.8 (3)
N2—C6—C7—C8−3.0 (4)C16—C15—C45—C46−68.4 (4)
C5—C6—C7—C8176.2 (3)C14—C15—C45—C50−69.1 (4)
C6—C7—C8—C92.2 (4)C16—C15—C45—C50111.7 (3)
C6—N2—C9—C10179.4 (3)C50—C45—C46—C47−0.7 (5)
Fe1—N2—C9—C10−7.3 (5)C15—C45—C46—C47179.4 (3)
C6—N2—C9—C8−1.2 (4)C45—C46—C47—C480.7 (5)
Fe1—N2—C9—C8172.1 (2)C46—C47—C48—C49−0.4 (6)
C7—C8—C9—N2−0.7 (4)C47—C48—C49—C500.1 (6)
C7—C8—C9—C10178.8 (3)C48—C49—C50—C45−0.1 (5)
N2—C9—C10—C116.5 (5)C48—C49—C50—N7177.7 (3)
C8—C9—C10—C11−172.8 (3)C46—C45—C50—C490.4 (5)
N2—C9—C10—C33−167.5 (3)C15—C45—C50—C49−179.7 (3)
C8—C9—C10—C3313.2 (5)C46—C45—C50—N7−177.4 (3)
C14—N3—C11—C10−179.7 (3)C15—C45—C50—N72.5 (5)
Fe1—N3—C11—C10−2.8 (4)C51—N7—C50—C49117.2 (4)
C14—N3—C11—C121.1 (3)C51—N7—C50—C45−64.9 (4)
Fe1—N3—C11—C12178.1 (2)C50—N7—C51—O3−9.8 (5)
C9—C10—C11—N3−1.3 (5)C50—N7—C51—C52171.3 (3)
C33—C10—C11—N3172.8 (3)O3—C51—C52—C53143.9 (4)
C9—C10—C11—C12177.7 (3)N7—C51—C52—C53−37.0 (5)
C33—C10—C11—C12−8.2 (4)O3—C51—C52—C56−33.3 (5)
N3—C11—C12—C13−1.4 (4)N7—C51—C52—C56145.7 (3)
C10—C11—C12—C13179.4 (3)C56—C52—C53—C54−1.2 (6)
C11—C12—C13—C141.1 (4)C51—C52—C53—C54−178.4 (4)
C11—N3—C14—C15178.5 (3)C52—C53—C54—C550.3 (7)
Fe1—N3—C14—C151.5 (4)C56—N11—C55—C54−0.3 (7)
C11—N3—C14—C13−0.5 (3)C53—C54—C55—N110.6 (7)
Fe1—N3—C14—C13−177.4 (2)C55—N11—C56—C52−0.7 (7)
C12—C13—C14—N3−0.4 (4)C53—C52—C56—N111.5 (6)
C12—C13—C14—C15−179.4 (3)C51—C52—C56—N11178.8 (4)
N3—C14—C15—C162.6 (5)C19—C20—C57—C62−66.4 (4)
C13—C14—C15—C16−178.5 (3)C1—C20—C57—C62117.7 (4)
N3—C14—C15—C45−176.5 (3)C19—C20—C57—C58115.2 (4)
C13—C14—C15—C452.3 (4)C1—C20—C57—C58−60.7 (4)
C19—N4—C16—C15179.9 (3)C62—C57—C58—C59−1.7 (6)
Fe1—N4—C16—C150.9 (4)C20—C57—C58—C59176.8 (4)
C19—N4—C16—C171.6 (3)C57—C58—C59—C601.0 (7)
Fe1—N4—C16—C17−177.5 (2)C58—C59—C60—C610.0 (8)
C14—C15—C16—N4−3.9 (5)C59—C60—C61—C62−0.3 (7)
C45—C15—C16—N4175.3 (3)C60—C61—C62—C57−0.4 (6)
C14—C15—C16—C17174.2 (3)C60—C61—C62—N8−177.6 (4)
C45—C15—C16—C17−6.6 (4)C58—C57—C62—C611.3 (5)
N4—C16—C17—C18−1.0 (4)C20—C57—C62—C61−177.0 (3)
C15—C16—C17—C18−179.4 (3)C58—C57—C62—N8178.5 (3)
C16—C17—C18—C19−0.1 (4)C20—C57—C62—N80.1 (5)
C16—N4—C19—C20174.1 (3)C63—N8—C62—C61−51.0 (5)
Fe1—N4—C19—C20−6.9 (4)C63—N8—C62—C57131.8 (4)
C16—N4—C19—C18−1.6 (3)C62—N8—C63—O4−4.4 (5)
Fe1—N4—C19—C18177.4 (2)C62—N8—C63—C64174.8 (3)
C17—C18—C19—N41.1 (4)O4—C63—C64—C65−135.2 (5)
C17—C18—C19—C20−174.7 (3)N8—C63—C64—C6545.6 (5)
N4—C19—C20—C10.6 (5)O4—C63—C64—C6844.9 (6)
C18—C19—C20—C1175.7 (3)N8—C63—C64—C68−134.3 (4)
N4—C19—C20—C57−175.1 (3)C66—N12—C65—C64−0.6 (9)
C18—C19—C20—C570.0 (5)C68—C64—C65—N12−0.4 (8)
N1—C1—C20—C197.3 (5)C63—C64—C65—N12179.7 (5)
C2—C1—C20—C19−176.4 (3)C65—N12—C66—C672.1 (10)
N1—C1—C20—C57−177.0 (3)N12—C66—C67—C68−2.5 (10)
C2—C1—C20—C57−0.6 (5)C66—C67—C68—C641.4 (9)
C6—C5—C21—C22−72.0 (5)C65—C64—C68—C670.0 (8)
C4—C5—C21—C22114.3 (4)C63—C64—C68—C67179.9 (5)
C6—C5—C21—C26106.3 (4)C70—N13—C69—C711.0 (5)
C4—C5—C21—C26−67.4 (4)Fe1—N13—C69—C71176.8 (3)
C26—C21—C22—C23−0.7 (6)C69—N13—C70—N14−1.2 (5)
C5—C21—C22—C23177.7 (4)Fe1—N13—C70—N14−177.0 (3)
C21—C22—C23—C240.3 (6)C71—N14—C70—N131.0 (5)
C22—C23—C24—C25−0.5 (7)C72—N14—C70—N13177.5 (4)
C23—C24—C25—C261.1 (7)C70—N14—C71—C69−0.3 (5)
C24—C25—C26—C21−1.5 (6)C72—N14—C71—C69−176.8 (5)
C24—C25—C26—N5178.0 (4)N13—C69—C71—N14−0.4 (5)
C22—C21—C26—C251.3 (6)C75—N15—C73—N160.0 (4)
C5—C21—C26—C25−177.1 (4)Fe1—N15—C73—N16−179.7 (2)
C22—C21—C26—N5−178.2 (3)C74—N16—C73—N150.0 (4)
C5—C21—C26—N53.4 (5)C76—N16—C73—N15177.6 (3)
C27—N5—C26—C25−4.4 (7)C73—N16—C74—C750.1 (5)
C27—N5—C26—C21175.1 (4)C76—N16—C74—C75−177.6 (4)
C26—N5—C27—O112.7 (7)N16—C74—C75—N15−0.1 (5)
C26—N5—C27—C28−166.9 (4)C73—N15—C75—C740.1 (4)
O1—C27—C28—C29−158.4 (4)Fe1—N15—C75—C74179.8 (3)
N5—C27—C28—C2921.3 (6)C80—O5—C78—C77−1.9 (9)
O1—C27—C28—C3217.6 (6)C79—C77—C78—O521.6 (9)
N5—C27—C28—C32−162.8 (4)C78—C77—C79—C80−32.8 (8)
C30—N9—C29—C280.8 (6)C78—O5—C80—C79−20.6 (10)
C32—C28—C29—N9−1.0 (6)C77—C79—C80—O533.4 (9)
C27—C28—C29—N9175.0 (4)C84—O6—C81—C82−12.7 (16)
C29—N9—C30—C310.2 (7)O6—C81—C82—C83−5 (2)
N9—C30—C31—C32−0.8 (9)C81—C82—C83—C8418 (2)
C30—C31—C32—C280.6 (8)C81—O6—C84—C8326.4 (15)
C29—C28—C32—C310.3 (7)C82—C83—C84—O6−25.4 (16)
C27—C28—C32—C31−176.0 (4)C86—N18—C85—C87−0.8 (5)
C9—C10—C33—C38−72.8 (4)C85—N18—C86—N171.1 (5)
C11—C10—C33—C38112.8 (4)C87—N17—C86—N18−1.1 (5)
C9—C10—C33—C34107.1 (3)C88—N17—C86—N18180.0 (4)
C11—C10—C33—C34−67.3 (4)C86—N17—C87—C850.5 (5)
C38—C33—C34—C350.1 (5)C88—N17—C87—C85179.5 (4)
C10—C33—C34—C35−179.8 (3)N18—C85—C87—N170.2 (5)
C33—C34—C35—C360.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N6—H6···O4i0.882.182.948 (4)145
N8—H8···N90.882.193.018 (5)156
Symmetry code: (i) x, y+1, z.
 

Funding information

Funding for this research was provided by: National Natural Science Foundation of China (grant No. 21771176 to JL; grant No. 21977093 to JL); Strategic Priority Research Program of Chinese Academy of Sciences (grant No. XDB28000000).

References

First citationAldilla, V. R., Bhadbhade, M., Bhattacharyya, S., Kumar, N., Rich, A. M. & Marjo, C. E. (2017). CrystEngComm, 19, 4749–4758.  Web of Science CSD CrossRef CAS Google Scholar
 First citationAllen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335–338.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationBertolasi, V., Gilli, P., Ferretti, V. & Gilli, G. (1995). Acta Cryst. B51, 1004–1015.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationBruker (2013). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBruker (2016). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationGunter, M. J., McLaughlin, G. M., Berry, K. J., Murray, K. S., Irving, M. & Clark, P. E. (1984). Inorg. Chem. 23, 283–300.  CSD CrossRef CAS Google Scholar
 First citationHe, B., Schulz, C. E. & Li, J. (2015). Dalton Trans. 44, 13651–13661.  CSD CrossRef CAS PubMed Google Scholar
 First citationLeigh, D. A., Robertson, C. C., Slawin, A. M. Z. & Thomson, P. I. T. (2013). J. Am. Chem. Soc. 135, 9939–9943.  Web of Science CSD CrossRef CAS PubMed Google Scholar
 First citationLi, J., Nair, S. M., Noll, B. C., Schulz, C. E. & Scheidt, W. R. (2008). Inorg. Chem. 47, 3841–3850.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationMacrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M. & Wood, P. A. (2020). J. Appl. Cryst. 53, 226–235.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationMalinovskii, S. T., Simonov, Y. A. & Ganin, É. V. (2001). Crystallogr. Rep. 46, 419–424.  CrossRef Google Scholar
 First citationPitcher, R. S. & Watmough, N. J. (2004). Biochim. Biophys. Acta, 1655, 388–399.  CrossRef PubMed CAS Google Scholar
 First citationPrasad, N. & Govil, G. (1980). Proc. Indian Acad. Sci. Chem. Sci. 89, 253–262.  CAS Google Scholar
 First citationScheidt, W. R. & Reed, C. A. (1981). Chem. Rev. 81, 543–555.  CrossRef CAS Web of Science Google Scholar
 First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationWalker, F. A. (2004). Chem. Rev. 104, 589–616.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationYao, Z., Schulz, C. E., Zhan, N. & Li, J. (2017). Inorg. Chem. 56, 12615–12624.  CSD CrossRef CAS PubMed Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 6| Part 5| May 2021|
https://doi.org/10.1107/S2414314621005319
Follow IUCr Journals
Sign up for e-alerts
E-alerts
Follow IUCr on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS