# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_K1_3
_database_code_depnum_ccdc_archive 'CCDC 1048055'
_audit_update_record             
;
2015-02-06 deposited with the CCDC.
2018-04-19 downloaded from the CCDC.
;

_audit_creation_method           'manual edited SHELXL-2014/6.cif file'

_chemical_compound_source        'synthetical product'

_chemical_name_systematic        
; chloro-bis[2-(1-methyl-1H-pyrazol-3-yl)phenolato-N,O]-iron(III)
;
_chemical_name_common            
; chloro-bis[2-(1-methyl-1H-pyrazol-3-yl)phenolato-N,O]-iron(III)
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 Cl Fe N4 O2'
_chemical_formula_sum            'C20 H18 Cl Fe N4 O2'
_chemical_formula_weight         437.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.1475(6)
_cell_length_b                   11.7295(5)
_cell_length_c                   11.9893(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.0920(10)
_cell_angle_gamma                90
_cell_volume                     1891.18(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9360
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      30.84

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_F_000             900
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.963
_shelx_estimated_absorpt_T_min   0.761
_shelx_estimated_absorpt_T_max   0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.503
_exptl_absorpt_correction_T_max  0.647
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25391
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5517
_reflns_number_gt                5072
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     ?
_reflns_Friedel_fraction_full    ?

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'modified ORTEP (Johnson, 1965)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'

_refine_special_details          
;
 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.
 
 The non-hydrogen atoms were refined with anisotropic displacement parameters
 without any constraints.
 
 The H atoms of the pyrazole and of the phenyl rings were put at the external
 bisectors of the C-C-X angles at C-H distance of 0.95 Å and one common
 isotropic displacement parameter was refined for the H atoms of the same ring
 (AFIX 43 of SHELXL).

 The H atoms of the methyl groups were refined with common isotropic
 displacement parameters for the H atoms of the same group and idealized
 geometries with tetrahedral angles, enabling rotation around the N-C bond,
 and C-H distances of 0.98 Å (AFIX 137 of SHELXL).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²+0.9593P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5517
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0747
_refine_ls_wR_factor_gt          0.0722
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.77735(2) 0.55501(2) 0.70607(2) 0.01235(5) Uani 1 1 d . . . . .
Cl1 Cl 0.72546(2) 0.41150(3) 0.80000(2) 0.02012(7) Uani 1 1 d . . . . .
N11 N 0.85421(7) 0.67700(8) 0.94957(8) 0.01517(18) Uani 1 1 d . . . . .
N12 N 0.87794(7) 0.62388(8) 0.86125(8) 0.01338(17) Uani 1 1 d . . . . .
C13 C 0.97851(8) 0.61794(9) 0.89581(9) 0.01309(19) Uani 1 1 d . . . . .
C14 C 1.01745(8) 0.66832(10) 1.00720(10) 0.0163(2) Uani 1 1 d . . . . .
H14 H 1.0855 0.6760 1.0519 0.020(3) Uiso 1 1 calc R U . . .
C15 C 0.93626(8) 0.70419(10) 1.03768(10) 0.0173(2) Uani 1 1 d . . . . .
H15 H 0.9379 0.7416 1.1085 0.020(3) Uiso 1 1 calc R U . . .
C16 C 0.75201(8) 0.69482(11) 0.94719(11) 0.0198(2) Uani 1 1 d . . . . .
H161 H 0.7511 0.7247 1.0232 0.032(3) Uiso 1 1 calc R U . . .
H162 H 0.7160 0.6222 0.9315 0.032(3) Uiso 1 1 calc R U . . .
H163 H 0.7199 0.7496 0.8853 0.032(3) Uiso 1 1 calc R U . . .
O21 O 0.88912(6) 0.53409(8) 0.65754(7) 0.01879(17) Uani 1 1 d . . . . .
C21 C 0.98655(8) 0.52117(10) 0.71195(10) 0.0155(2) Uani 1 1 d . . . . .
C22 C 1.03350(8) 0.56288(9) 0.82570(10) 0.01380(19) Uani 1 1 d . . . . .
C23 C 1.13681(8) 0.54837(10) 0.87441(11) 0.0179(2) Uani 1 1 d . . . . .
H23 H 1.1692 0.5762 0.9512 0.027(2) Uiso 1 1 calc R U . . .
C24 C 1.19239(9) 0.49458(11) 0.81322(12) 0.0220(2) Uani 1 1 d . . . . .
H24 H 1.2623 0.4868 0.8473 0.027(2) Uiso 1 1 calc R U . . .
C25 C 1.14523(9) 0.45189(11) 0.70132(13) 0.0241(3) Uani 1 1 d . . . . .
H25 H 1.1829 0.4141 0.6592 0.027(2) Uiso 1 1 calc R U . . .
C26 C 1.04358(9) 0.46455(11) 0.65159(11) 0.0219(2) Uani 1 1 d . . . . .
H26 H 1.0118 0.4346 0.5755 0.027(2) Uiso 1 1 calc R U . . .
N31 N 0.69446(7) 0.40994(8) 0.47714(9) 0.01712(18) Uani 1 1 d . . . . .
N32 N 0.68544(7) 0.50646(8) 0.53563(8) 0.01477(17) Uani 1 1 d . . . . .
C33 C 0.60284(8) 0.55965(9) 0.46720(9) 0.01301(19) Uani 1 1 d . . . . .
C34 C 0.56001(9) 0.49510(10) 0.36514(10) 0.0168(2) Uani 1 1 d . . . . .
H34 H 0.5017 0.5125 0.3024 0.022(3) Uiso 1 1 calc R U . . .
C35 C 0.62061(9) 0.40119(10) 0.37543(10) 0.0183(2) Uani 1 1 d . . . . .
H35 H 0.6117 0.3409 0.3202 0.022(3) Uiso 1 1 calc R U . . .
C36 C 0.77441(10) 0.32892(11) 0.52433(13) 0.0271(3) Uani 1 1 d . . . . .
H361 H 0.7629 0.2609 0.4744 0.038(3) Uiso 1 1 calc R U . . .
H362 H 0.7764 0.3073 0.6040 0.038(3) Uiso 1 1 calc R U . . .
H363 H 0.8379 0.3638 0.5265 0.038(3) Uiso 1 1 calc R U . . .
O41 O 0.69939(6) 0.68574(7) 0.68197(7) 0.01620(16) Uani 1 1 d . . . . .
C41 C 0.61393(8) 0.72262(9) 0.60701(9) 0.01328(19) Uani 1 1 d . . . . .
C42 C 0.56624(8) 0.66676(9) 0.50050(9) 0.01331(19) Uani 1 1 d . . . . .
C43 C 0.47963(8) 0.71564(10) 0.42429(10) 0.0183(2) Uani 1 1 d . . . . .
H43 H 0.4476 0.6797 0.3513 0.026(2) Uiso 1 1 calc R U . . .
C44 C 0.43979(9) 0.81505(11) 0.45297(11) 0.0220(2) Uani 1 1 d . . . . .
H44 H 0.3813 0.8470 0.3999 0.026(2) Uiso 1 1 calc R U . . .
C45 C 0.48574(9) 0.86801(10) 0.55991(11) 0.0200(2) Uani 1 1 d . . . . .
H45 H 0.4578 0.9352 0.5809 0.026(2) Uiso 1 1 calc R U . . .
C46 C 0.57229(8) 0.82268(10) 0.63570(10) 0.0163(2) Uani 1 1 d . . . . .
H46 H 0.6039 0.8598 0.7081 0.026(2) Uiso 1 1 calc R U . . .


_geom_special_details            
;
 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.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 O21 1.8630(8) . yes
Fe1 O41 1.8583(8) . yes
Fe1 N12 2.1201(9) . yes
Fe1 N32 2.1309(9) . yes
Fe1 Cl1 2.2703(3) . yes
N11 C15 1.3430(14) . yes
N11 N12 1.3575(13) . yes
N11 C16 1.4523(14) . yes
N12 C13 1.3545(13) . yes
C13 C14 1.4069(15) . yes
C13 C22 1.4611(15) . ?
C14 C15 1.3750(16) . yes
C14 H14 0.95 . ?
C15 H15 0.95 . ?
C16 H161 0.98 . ?
C16 H162 0.98 . ?
C16 H163 0.98 . ?
O21 C21 1.3379(13) . yes
C21 C22 1.4063(15) . ?
C21 C26 1.4066(16) . ?
C22 C23 1.4057(15) . ?
C23 C24 1.3830(17) . ?
C23 H23 0.95 . ?
C24 C25 1.3928(19) . ?
C24 H24 0.95 . ?
C25 C26 1.3831(17) . ?
C25 H25 0.95 . ?
C26 H26 0.95 . ?
N31 C35 1.3408(15) . yes
N31 N32 1.3584(13) . yes
N31 C36 1.4509(16) . yes
N32 C33 1.3537(14) . yes
C33 C34 1.4062(15) . yes
C33 C42 1.4609(15) . ?
C34 C35 1.3776(17) . yes
C34 H34 0.95 . ?
C35 H35 0.95 . ?
C36 H361 0.98 . ?
C36 H362 0.98 . ?
C36 H363 0.98 . ?
O41 C41 1.3349(12) . yes
C41 C46 1.4030(15) . ?
C41 C42 1.4071(15) . ?
C42 C43 1.4033(15) . ?
C43 C44 1.3842(17) . ?
C43 H43 0.95 . ?
C44 C45 1.3909(18) . ?
C44 H44 0.95 . ?
C45 C46 1.3845(16) . ?
C45 H45 0.95 . ?
C46 H46 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N12 Fe1 N32 170.68(4) . . yes
O41 Fe1 O21 125.49(4) . . yes
O21 Fe1 Cl1 119.59(3) . . yes
O41 Fe1 Cl1 114.91(3) . . yes
O41 Fe1 N12 91.51(4) . . yes
O21 Fe1 N12 85.45(4) . . yes
O41 Fe1 N32 85.15(4) . . yes
O21 Fe1 N32 89.41(4) . . yes
N12 Fe1 Cl1 94.56(3) . . yes
N32 Fe1 Cl1 94.73(3) . . yes
C15 N11 N12 111.08(9) . . yes
C15 N11 C16 126.39(10) . . yes
N12 N11 C16 122.46(9) . . yes
C13 N12 N11 106.01(9) . . yes
C13 N12 Fe1 127.15(7) . . yes
N11 N12 Fe1 126.73(7) . . yes
N12 C13 C14 109.46(9) . . ?
N12 C13 C22 122.90(10) . . ?
C14 C13 C22 127.61(10) . . ?
C15 C14 C13 105.52(10) . . ?
C15 C14 H14 127.2 . . ?
C13 C14 H14 127.2 . . ?
N11 C15 C14 107.92(10) . . ?
N11 C15 H15 126.0 . . ?
C14 C15 H15 126.0 . . ?
N11 C16 H161 109.5 . . ?
N11 C16 H162 109.5 . . ?
H161 C16 H162 109.5 . . ?
N11 C16 H163 109.5 . . ?
H161 C16 H163 109.5 . . ?
H162 C16 H163 109.5 . . ?
C21 O21 Fe1 135.11(8) . . yes
O21 C21 C22 122.56(10) . . ?
O21 C21 C26 118.12(10) . . ?
C22 C21 C26 119.31(10) . . ?
C23 C22 C21 118.54(10) . . ?
C23 C22 C13 119.03(10) . . ?
C21 C22 C13 122.42(10) . . ?
C24 C23 C22 121.60(11) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C23 C24 C25 119.59(11) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 119.96(11) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C21 120.98(12) . . ?
C25 C26 H26 119.5 . . ?
C21 C26 H26 119.5 . . ?
C35 N31 N32 111.21(10) . . yes
C35 N31 C36 126.68(10) . . yes
N32 N31 C36 122.10(10) . . yes
C33 N32 N31 105.85(9) . . yes
C33 N32 Fe1 127.79(7) . . yes
N31 N32 Fe1 126.20(7) . . yes
N32 C33 C34 109.68(10) . . ?
N32 C33 C42 122.91(10) . . ?
C34 C33 C42 127.40(10) . . ?
C35 C34 C33 105.34(10) . . ?
C35 C34 H34 127.3 . . ?
C33 C34 H34 127.3 . . ?
N31 C35 C34 107.92(10) . . ?
N31 C35 H35 126.0 . . ?
C34 C35 H35 126.0 . . ?
N31 C36 H361 109.5 . . ?
N31 C36 H362 109.5 . . ?
H361 C36 H362 109.5 . . ?
N31 C36 H363 109.5 . . ?
H361 C36 H363 109.5 . . ?
H362 C36 H363 109.5 . . ?
C41 O41 Fe1 137.89(7) . . yes
O41 C41 C46 117.87(10) . . ?
O41 C41 C42 122.61(10) . . ?
C46 C41 C42 119.51(10) . . ?
C43 C42 C41 118.44(10) . . ?
C43 C42 C33 119.03(10) . . ?
C41 C42 C33 122.53(9) . . ?
C44 C43 C42 121.53(11) . . ?
C44 C43 H43 119.2 . . ?
C42 C43 H43 119.2 . . ?
C43 C44 C45 119.70(11) . . ?
C43 C44 H44 120.2 . . ?
C45 C44 H44 120.2 . . ?
C46 C45 C44 119.89(11) . . ?
C46 C45 H45 120.1 . . ?
C44 C45 H45 120.1 . . ?
C45 C46 C41 120.89(11) . . ?
C45 C46 H46 119.6 . . ?
C41 C46 H46 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 N12 Fe1 176.40(8) . . . . yes
C16 N11 N12 Fe1 -0.76(15) . . . . yes
Fe1 N12 C13 C14 -176.49(7) . . . . yes
Fe1 N12 C13 C22 1.60(15) . . . . yes
C15 N11 N12 C13 -0.04(12) . . . . yes
C16 N11 N12 C13 -177.20(10) . . . . yes
N11 N12 C13 C14 -0.07(12) . . . . yes
N11 N12 C13 C22 178.01(10) . . . . ?
N12 C13 C14 C15 0.15(13) . . . . yes
C22 C13 C14 C15 -177.82(11) . . . . ?
C16 N11 C15 C14 177.15(11) . . . . ?
C13 C14 C15 N11 -0.16(13) . . . . yes
C14 C15 N11 N12 0.13(13) . . . . yes
O41 Fe1 O21 C21 113.58(11) . . . . ?
N12 Fe1 O21 C21 24.98(11) . . . . ?
N32 Fe1 O21 C21 -162.80(11) . . . . ?
Cl1 Fe1 O21 C21 -67.69(12) . . . . ?
Fe1 O21 C21 C22 -25.02(18) . . . . yes
Fe1 O21 C21 C26 155.66(10) . . . . yes
O21 C21 C22 C23 -178.06(11) . . . . ?
C26 C21 C22 C23 1.25(17) . . . . ?
O21 C21 C22 C13 3.53(17) . . . . ?
C26 C21 C22 C13 -177.16(11) . . . . ?
N12 C13 C22 C23 -172.33(10) . . . . ?
C14 C13 C22 C23 5.39(17) . . . . ?
N12 C13 C22 C21 6.07(17) . . . . ?
C14 C13 C22 C21 -176.21(11) . . . . ?
C21 C22 C23 C24 0.06(17) . . . . ?
C13 C22 C23 C24 178.52(11) . . . . ?
C22 C23 C24 C25 -1.05(19) . . . . ?
C23 C24 C25 C26 0.7(2) . . . . ?
C24 C25 C26 C21 0.6(2) . . . . ?
O21 C21 C26 C25 177.74(12) . . . . ?
C22 C21 C26 C25 -1.60(19) . . . . ?
C36 N31 N32 C33 -179.09(11) . . . . ?
C35 N31 N32 Fe1 175.59(8) . . . . yes
C36 N31 N32 Fe1 -3.35(16) . . . . yes
Fe1 N32 C33 C34 -175.51(8) . . . . yes
N31 N32 C33 C42 178.92(10) . . . . ?
Fe1 N32 C33 C42 3.27(15) . . . . yes
C35 N31 N32 C33 -0.16(13) . . . . yes
N31 N32 C33 C34 0.15(12) . . . . yes
N32 C33 C34 C35 -0.09(13) . . . . yes
C42 C33 C34 C35 -178.79(11) . . . . ?
C36 N31 C35 C34 178.98(12) . . . . ?
C33 C34 C35 N31 -0.01(13) . . . . yes
C34 C35 N31 N32 0.10(14) . . . . yes
O21 Fe1 O41 C41 98.52(11) . . . . ?
N12 Fe1 O41 C41 -175.99(11) . . . . ?
N32 Fe1 O41 C41 12.72(11) . . . . ?
Cl1 Fe1 O41 C41 -80.26(11) . . . . ?
Fe1 O41 C41 C42 -13.71(17) . . . . yes
Fe1 O41 C41 C46 167.81(8) . . . . yes
O41 C41 C42 C43 -176.38(10) . . . . ?
C46 C41 C42 C43 2.07(16) . . . . ?
O41 C41 C42 C33 4.30(16) . . . . ?
C46 C41 C42 C33 -177.24(10) . . . . ?
N32 C33 C42 C43 -179.71(10) . . . . ?
C34 C33 C42 C43 -1.16(17) . . . . ?
N32 C33 C42 C41 -0.40(16) . . . . ?
C34 C33 C42 C41 178.15(11) . . . . ?
C41 C42 C43 C44 -1.43(17) . . . . ?
C33 C42 C43 C44 177.91(11) . . . . ?
C42 C43 C44 C45 -0.41(19) . . . . ?
C43 C44 C45 C46 1.59(19) . . . . ?
C44 C45 C46 C41 -0.93(18) . . . . ?
O41 C41 C46 C45 177.60(10) . . . . ?
C42 C41 C46 C45 -0.93(17) . . . . ?

_refine_diff_density_max         0.543
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.061

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_BSK8_3
_database_code_depnum_ccdc_archive 'CCDC 1048056'
_audit_update_record             
;
2015-02-06 deposited with the CCDC.
2018-04-19 downloaded from the CCDC.
;

_audit_creation_method           'manual edited SHELXL-2014/6.cif file'

_chemical_compound_source        'synthetical product'

_chemical_name_systematic        
; (m2-oxo)-bis(bis(2-(1-methyl-1H-pyrazol-3-yl)phenolato-N,O)-iron(III))
;
_chemical_name_common            
; (m2-oxo)-bis(bis(2-(1-methyl-1H-pyrazol-3-yl)phenolato-N,O)-iron(III))
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H36 Fe2 N8 O5'
_chemical_formula_sum            'C40 H36 Fe2 N8 O5'
_chemical_formula_weight         820.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   18.4514(10)
_cell_length_b                   19.5777(11)
_cell_length_c                   20.1490(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7278.5(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8833
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      30.60

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_F_000             3392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.855
_shelx_estimated_absorpt_T_min   0.796
_shelx_estimated_absorpt_T_max   0.868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.762
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31306
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10603
_reflns_number_gt                7956
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     ?
_reflns_Friedel_fraction_full    ?

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'modified ORTEP (Johnson, 1965)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'

_refine_special_details          
;
 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.
 
 The non-hydrogen atoms were refined with anisotropic displacement parameters
 without any constraints.
 
 The H atoms of the phenyl rings as well as those of the pyrazole rings were
 put at the external bisectors of the C-C-C angles at C-H distances of 0.95 Å
 and common isotropic displacement parameters were refined for the H atoms of
 the same ring (AFIX 43 of SHELXL).
 
 The H atoms of the methyl groups were refined with common isotropic
 displacement parameters for the H atoms of the same group and idealized
 geometries with tetrahedral angles, enabling rotation around the N-C bond,
 and C-H distances of 0.98 Å (AFIX 137 of SHELXL).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²+2.5747P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         10603
_refine_ls_number_parameters     512
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0910
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.50418(5) 0.73977(6) 0.62499(5) 0.0190(2) Uani 1 1 d . . . . .
Fe1 Fe 0.43991(2) 0.74184(2) 0.55848(2) 0.01231(6) Uani 1 1 d . . . . .
C11 C 0.38224(10) 0.86549(9) 0.66413(9) 0.0273(4) Uani 1 1 d . . . . .
H111 H 0.3616 0.9009 0.6929 0.059(5) Uiso 1 1 calc R U . . .
H112 H 0.3849 0.8826 0.6185 0.059(5) Uiso 1 1 calc R U . . .
H113 H 0.4310 0.8537 0.6796 0.059(5) Uiso 1 1 calc R U . . .
N11 N 0.33623(7) 0.80473(7) 0.66618(7) 0.0205(3) Uani 1 1 d . . . . .
N12 N 0.34831(7) 0.75153(6) 0.62400(7) 0.0164(3) Uani 1 1 d . . . . .
C13 C 0.30010(8) 0.70264(8) 0.64120(7) 0.0156(3) Uani 1 1 d . . . . .
C14 C 0.25752(9) 0.72576(9) 0.69487(8) 0.0211(3) Uani 1 1 d . . . . .
H14 H 0.2198 0.7016 0.7169 0.029(4) Uiso 1 1 calc R U . . .
C15 C 0.28197(9) 0.79033(10) 0.70856(9) 0.0239(4) Uani 1 1 d . . . . .
H15 H 0.2638 0.8198 0.7421 0.029(4) Uiso 1 1 calc R U . . .
O21 O 0.39297(6) 0.66025(6) 0.52931(6) 0.0189(2) Uani 1 1 d . . . . .
C21 C 0.34058(8) 0.61977(8) 0.55173(8) 0.0161(3) Uani 1 1 d . . . . .
C22 C 0.29481(8) 0.63713(8) 0.60584(8) 0.0164(3) Uani 1 1 d . . . . .
C23 C 0.24089(9) 0.59040(9) 0.62530(9) 0.0254(4) Uani 1 1 d . . . . .
H23 H 0.2108 0.6012 0.6621 0.031(3) Uiso 1 1 calc R U . . .
C24 C 0.23036(10) 0.52917(10) 0.59237(11) 0.0326(4) Uani 1 1 d . . . . .
H24 H 0.1935 0.4985 0.6064 0.031(3) Uiso 1 1 calc R U . . .
C25 C 0.27418(10) 0.51289(9) 0.53860(10) 0.0283(4) Uani 1 1 d . . . . .
H25 H 0.2669 0.4712 0.5155 0.031(3) Uiso 1 1 calc R U . . .
C26 C 0.32844(9) 0.55724(8) 0.51854(9) 0.0209(3) Uani 1 1 d . . . . .
H26 H 0.3581 0.5454 0.4817 0.031(3) Uiso 1 1 calc R U . . .
C31 C 0.55884(9) 0.61767(8) 0.51693(9) 0.0220(3) Uani 1 1 d . . . . .
H311 H 0.5963 0.5846 0.5046 0.032(3) Uiso 1 1 calc R U . . .
H312 H 0.5109 0.5980 0.5085 0.032(3) Uiso 1 1 calc R U . . .
H313 H 0.5634 0.6289 0.5641 0.032(3) Uiso 1 1 calc R U . . .
N31 N 0.56761(7) 0.67941(7) 0.47757(7) 0.0175(3) Uani 1 1 d . . . . .
N32 N 0.52071(7) 0.73296(6) 0.48385(6) 0.0149(2) Uani 1 1 d . . . . .
C33 C 0.54438(8) 0.78173(8) 0.44169(7) 0.0152(3) Uani 1 1 d . . . . .
C34 C 0.60642(9) 0.75795(9) 0.40797(9) 0.0219(3) Uani 1 1 d . . . . .
H34 H 0.6339 0.7817 0.3754 0.032(4) Uiso 1 1 calc R U . . .
C35 C 0.61891(9) 0.69339(9) 0.43200(9) 0.0223(3) Uani 1 1 d . . . . .
H35 H 0.6571 0.6638 0.4188 0.032(4) Uiso 1 1 calc R U . . .
O41 O 0.41784(6) 0.82722(6) 0.51864(6) 0.0191(2) Uani 1 1 d . . . . .
C41 C 0.44982(8) 0.86885(8) 0.47506(8) 0.0157(3) Uani 1 1 d . . . . .
C42 C 0.50949(8) 0.84885(8) 0.43534(8) 0.0164(3) Uani 1 1 d . . . . .
C43 C 0.53687(9) 0.89570(9) 0.38867(9) 0.0233(4) Uani 1 1 d . . . . .
H43 H 0.5761 0.8824 0.3610 0.032(3) Uiso 1 1 calc R U . . .
C44 C 0.50818(10) 0.96082(10) 0.38201(9) 0.0293(4) Uani 1 1 d . . . . .
H44 H 0.5275 0.9916 0.3501 0.032(3) Uiso 1 1 calc R U . . .
C45 C 0.45095(10) 0.98062(9) 0.42235(9) 0.0268(4) Uani 1 1 d . . . . .
H45 H 0.4315 1.0254 0.4185 0.032(3) Uiso 1 1 calc R U . . .
C46 C 0.42209(9) 0.93543(8) 0.46818(9) 0.0208(3) Uani 1 1 d . . . . .
H46 H 0.3829 0.9496 0.4955 0.032(3) Uiso 1 1 calc R U . . .
Fe2 Fe 0.56860(2) 0.73764(2) 0.69134(2) 0.01206(6) Uani 1 1 d . . . . .
C51 C 0.43521(9) 0.62854(8) 0.73963(9) 0.0205(3) Uani 1 1 d . . . . .
H511 H 0.3946 0.6002 0.7547 0.033(3) Uiso 1 1 calc R U . . .
H512 H 0.4808 0.6042 0.7473 0.033(3) Uiso 1 1 calc R U . . .
H513 H 0.4299 0.6381 0.6921 0.033(3) Uiso 1 1 calc R U . . .
N51 N 0.43562(7) 0.69253(7) 0.77640(7) 0.0173(3) Uani 1 1 d . . . . .
N52 N 0.48753(7) 0.74100(6) 0.76634(6) 0.0147(2) Uani 1 1 d . . . . .
C53 C 0.47030(8) 0.79377(8) 0.80698(8) 0.0170(3) Uani 1 1 d . . . . .
C54 C 0.40745(9) 0.77744(9) 0.84353(8) 0.0229(3) Uani 1 1 d . . . . .
H54 H 0.3836 0.8050 0.8756 0.030(4) Uiso 1 1 calc R U . . .
C55 C 0.38796(9) 0.71302(9) 0.82275(8) 0.0229(4) Uani 1 1 d . . . . .
H55 H 0.3477 0.6874 0.8385 0.030(4) Uiso 1 1 calc R U . . .
O61 O 0.60445(6) 0.81878(6) 0.73124(6) 0.0208(2) Uani 1 1 d . . . . .
C61 C 0.57897(9) 0.86523(8) 0.77411(8) 0.0184(3) Uani 1 1 d . . . . .
C62 C 0.51381(9) 0.85634(8) 0.81021(8) 0.0188(3) Uani 1 1 d . . . . .
C63 C 0.49153(10) 0.90885(9) 0.85346(9) 0.0276(4) Uani 1 1 d . . . . .
H63 H 0.4472 0.9040 0.8770 0.038(3) Uiso 1 1 calc R U . . .
C64 C 0.53267(12) 0.96736(9) 0.86248(10) 0.0340(5) Uani 1 1 d . . . . .
H64 H 0.5164 1.0022 0.8917 0.038(3) Uiso 1 1 calc R U . . .
C65 C 0.59745(12) 0.97468(9) 0.82876(10) 0.0315(4) Uani 1 1 d . . . . .
H65 H 0.6265 1.0141 0.8359 0.038(3) Uiso 1 1 calc R U . . .
C66 C 0.62018(10) 0.92467(8) 0.78448(9) 0.0248(4) Uani 1 1 d . . . . .
H66 H 0.6643 0.9307 0.7609 0.038(3) Uiso 1 1 calc R U . . .
C71 C 0.63748(10) 0.85101(8) 0.57996(9) 0.0247(4) Uani 1 1 d . . . . .
H711 H 0.6596 0.8822 0.5477 0.035(3) Uiso 1 1 calc R U . . .
H712 H 0.6372 0.8725 0.6239 0.035(3) Uiso 1 1 calc R U . . .
H713 H 0.5876 0.8408 0.5664 0.035(3) Uiso 1 1 calc R U . . .
N71 N 0.67922(7) 0.78777(7) 0.58268(7) 0.0206(3) Uani 1 1 d . . . . .
N72 N 0.66098(7) 0.73686(6) 0.62566(7) 0.0161(3) Uani 1 1 d . . . . .
C73 C 0.70703(8) 0.68490(8) 0.61251(8) 0.0168(3) Uani 1 1 d . . . . .
C74 C 0.75459(9) 0.70398(10) 0.56089(8) 0.0242(4) Uani 1 1 d . . . . .
H74 H 0.7923 0.6773 0.5420 0.035(4) Uiso 1 1 calc R U . . .
C75 C 0.73483(9) 0.76915(10) 0.54373(9) 0.0264(4) Uani 1 1 d . . . . .
H75 H 0.7567 0.7963 0.5102 0.035(4) Uiso 1 1 calc R U . . .
O81 O 0.60473(6) 0.65116(6) 0.72006(6) 0.0199(2) Uani 1 1 d . . . . .
C81 C 0.64892(8) 0.60390(8) 0.69513(8) 0.0170(3) Uani 1 1 d . . . . .
C82 C 0.70202(8) 0.61857(8) 0.64633(8) 0.0181(3) Uani 1 1 d . . . . .
C83 C 0.74980(10) 0.56649(10) 0.62693(9) 0.0306(4) Uani 1 1 d . . . . .
H83 H 0.7871 0.5766 0.5959 0.042(3) Uiso 1 1 calc R U . . .
C84 C 0.74407(13) 0.50132(11) 0.65168(11) 0.0460(6) Uani 1 1 d . . . . .
H84 H 0.7772 0.4669 0.6379 0.042(3) Uiso 1 1 calc R U . . .
C85 C 0.68974(13) 0.48603(10) 0.69678(10) 0.0401(5) Uani 1 1 d . . . . .
H85 H 0.6843 0.4406 0.7125 0.042(3) Uiso 1 1 calc R U . . .
C86 C 0.64334(10) 0.53675(9) 0.71905(9) 0.0262(4) Uani 1 1 d . . . . .
H86 H 0.6072 0.5259 0.7510 0.042(3) Uiso 1 1 calc R U . . .


_geom_special_details            
;
 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.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 Fe1 1.7898(11) . yes
O1 Fe2 1.7893(11) . yes
Fe1 O21 1.9098(11) . yes
Fe1 O41 1.8986(11) . yes
Fe1 N12 2.1531(13) . yes
Fe1 N32 2.1246(13) . yes
C11 N11 1.462(2) . ?
C11 H111 0.98 . ?
C11 H112 0.98 . ?
C11 H113 0.98 . ?
N11 C15 1.346(2) . yes
N11 N12 1.3625(18) . yes
N12 C13 1.3519(19) . yes
C13 C14 1.411(2) . yes
C13 C22 1.470(2) . ?
C14 C15 1.370(3) . yes
C14 H14 0.95 . ?
C15 H15 0.95 . ?
O21 C21 1.3291(18) . yes
C21 C26 1.413(2) . ?
C21 C22 1.420(2) . ?
C22 C23 1.407(2) . ?
C23 C24 1.384(3) . ?
C23 H23 0.95 . ?
C24 C25 1.389(3) . ?
C24 H24 0.95 . ?
C25 C26 1.385(2) . ?
C25 H25 0.95 . ?
C26 H26 0.95 . ?
C31 N31 1.455(2) . ?
C31 H311 0.98 . ?
C31 H312 0.98 . ?
C31 H313 0.98 . ?
N31 C35 1.347(2) . yes
N31 N32 1.3653(17) . yes
N32 C33 1.351(2) . yes
C33 C34 1.410(2) . yes
C33 C42 1.469(2) . ?
C34 C35 1.373(2) . yes
C34 H34 0.95 . ?
C35 H35 0.95 . ?
O41 C41 1.3354(18) . yes
C41 C46 1.407(2) . ?
C41 C42 1.416(2) . ?
C42 C43 1.407(2) . ?
C43 C44 1.387(3) . ?
C43 H43 0.95 . ?
C44 C45 1.388(3) . ?
C44 H44 0.95 . ?
C45 C46 1.385(2) . ?
C45 H45 0.95 . ?
C46 H46 0.95 . ?
Fe2 O61 1.8993(11) . yes
Fe2 O81 1.9094(11) . yes
Fe2 N52 2.1273(13) . yes
Fe2 N72 2.1580(13) . yes
C51 N51 1.456(2) . ?
C51 H511 0.98 . ?
C51 H512 0.98 . ?
C51 H513 0.98 . ?
N51 C55 1.344(2) . yes
N51 N52 1.3635(17) . yes
N52 C53 1.356(2) . yes
C53 C54 1.411(2) . yes
C53 C62 1.466(2) . ?
C54 C55 1.377(2) . yes
C54 H54 0.95 . ?
C55 H55 0.95 . ?
O61 C61 1.3394(19) . yes
C61 C66 1.406(2) . ?
C61 C62 1.416(2) . ?
C62 C63 1.409(2) . ?
C63 C64 1.386(3) . ?
C63 H63 0.95 . ?
C64 C65 1.383(3) . ?
C64 H64 0.95 . ?
C65 C66 1.389(3) . ?
C65 H65 0.95 . ?
C66 H66 0.95 . ?
C71 N71 1.459(2) . ?
C71 H711 0.98 . ?
C71 H712 0.98 . ?
C71 H713 0.98 . ?
N71 C75 1.342(2) . yes
N71 N72 1.3626(18) . yes
N72 C73 1.352(2) . yes
C73 C74 1.411(2) . yes
C73 C82 1.470(2) . ?
C74 C75 1.371(3) . yes
C74 H74 0.95 . ?
C75 H75 0.95 . ?
O81 C81 1.3316(18) . yes
C81 C86 1.404(2) . ?
C81 C82 1.417(2) . ?
C82 C83 1.403(2) . ?
C83 C84 1.374(3) . ?
C83 H83 0.95 . ?
C84 C85 1.386(3) . ?
C84 H84 0.95 . ?
C85 C86 1.386(2) . ?
C85 H85 0.95 . ?
C86 H86 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Fe2 O1 Fe1 179.86(9) . . yes
N32 Fe1 N12 172.76(5) . . yes
O1 Fe1 O41 118.60(5) . . yes
O1 Fe1 O21 120.79(5) . . yes
O41 Fe1 O21 120.59(5) . . yes
O1 Fe1 N32 93.62(5) . . yes
O41 Fe1 N32 85.60(5) . . yes
O21 Fe1 N32 91.83(5) . . yes
O1 Fe1 N12 93.62(5) . . yes
O41 Fe1 N12 90.76(5) . . yes
O21 Fe1 N12 84.63(5) . . yes
N11 C11 H111 109.5 . . ?
N11 C11 H112 109.5 . . ?
H111 C11 H112 109.5 . . ?
N11 C11 H113 109.5 . . ?
H111 C11 H113 109.5 . . ?
H112 C11 H113 109.5 . . ?
C15 N11 N12 110.94(14) . . yes
C15 N11 C11 128.34(15) . . yes
N12 N11 C11 120.62(13) . . yes
C13 N12 N11 105.89(13) . . yes
C13 N12 Fe1 127.68(10) . . yes
N11 N12 Fe1 125.32(10) . . yes
N12 C13 C14 109.61(14) . . ?
N12 C13 C22 122.48(14) . . ?
C14 C13 C22 127.89(15) . . ?
C15 C14 C13 105.48(15) . . ?
C15 C14 H14 127.3 . . ?
C13 C14 H14 127.3 . . ?
N11 C15 C14 108.08(15) . . ?
N11 C15 H15 126.0 . . ?
C14 C15 H15 126.0 . . ?
C21 O21 Fe1 136.38(10) . . yes
O21 C21 C26 118.10(14) . . ?
O21 C21 C22 123.42(14) . . ?
C26 C21 C22 118.45(14) . . ?
C23 C22 C21 118.60(15) . . ?
C23 C22 C13 118.61(15) . . ?
C21 C22 C13 122.77(14) . . ?
C24 C23 C22 121.92(17) . . ?
C24 C23 H23 119.0 . . ?
C22 C23 H23 119.0 . . ?
C23 C24 C25 119.41(16) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C26 C25 C24 120.30(17) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C21 121.30(16) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
N31 C31 H311 109.5 . . ?
N31 C31 H312 109.5 . . ?
H311 C31 H312 109.5 . . ?
N31 C31 H313 109.5 . . ?
H311 C31 H313 109.5 . . ?
H312 C31 H313 109.5 . . ?
C35 N31 N32 110.65(13) . . yes
C35 N31 C31 128.22(14) . . yes
N32 N31 C31 121.13(13) . . yes
C33 N32 N31 106.24(12) . . yes
C33 N32 Fe1 127.90(10) . . yes
N31 N32 Fe1 124.97(10) . . yes
N32 C33 C34 109.40(14) . . ?
N32 C33 C42 123.06(14) . . ?
C34 C33 C42 127.53(15) . . ?
C35 C34 C33 105.69(15) . . ?
C35 C34 H34 127.2 . . ?
C33 C34 H34 127.2 . . ?
N31 C35 C34 108.03(14) . . ?
N31 C35 H35 126.0 . . ?
C34 C35 H35 126.0 . . ?
C41 O41 Fe1 136.10(10) . . yes
O41 C41 C46 118.00(14) . . ?
O41 C41 C42 123.12(14) . . ?
C46 C41 C42 118.88(14) . . ?
C43 C42 C41 118.45(15) . . ?
C43 C42 C33 118.94(14) . . ?
C41 C42 C33 122.60(14) . . ?
C44 C43 C42 121.78(16) . . ?
C44 C43 H43 119.1 . . ?
C42 C43 H43 119.1 . . ?
C43 C44 C45 119.37(16) . . ?
C43 C44 H44 120.3 . . ?
C45 C44 H44 120.3 . . ?
C46 C45 C44 120.30(16) . . ?
C46 C45 H45 119.9 . . ?
C44 C45 H45 119.9 . . ?
C45 C46 C41 121.17(16) . . ?
C45 C46 H46 119.4 . . ?
C41 C46 H46 119.4 . . ?
N52 Fe2 N72 172.41(5) . . yes
O1 Fe2 O61 121.88(5) . . yes
O1 Fe2 O81 118.62(5) . . yes
O61 Fe2 O81 119.45(5) . . yes
O1 Fe2 N52 93.61(5) . . yes
O61 Fe2 N52 85.31(5) . . yes
O81 Fe2 N52 93.30(5) . . yes
O1 Fe2 N72 93.82(5) . . yes
O61 Fe2 N72 89.45(5) . . yes
O81 Fe2 N72 84.48(5) . . yes
N51 C51 H511 109.5 . . ?
N51 C51 H512 109.5 . . ?
H511 C51 H512 109.5 . . ?
N51 C51 H513 109.5 . . ?
H511 C51 H513 109.5 . . ?
H512 C51 H513 109.5 . . ?
C55 N51 N52 110.81(14) . . yes
C55 N51 C51 127.38(14) . . yes
N52 N51 C51 121.80(13) . . yes
C53 N52 N51 106.00(12) . . yes
C53 N52 Fe2 128.13(11) . . yes
N51 N52 Fe2 125.31(10) . . yes
N52 C53 C54 109.60(14) . . ?
N52 C53 C62 122.34(14) . . ?
C54 C53 C62 128.05(15) . . ?
C55 C54 C53 105.27(14) . . ?
C55 C54 H54 127.4 . . ?
C53 C54 H54 127.4 . . ?
N51 C55 C54 108.30(15) . . ?
N51 C55 H55 125.9 . . ?
C54 C55 H55 125.9 . . ?
C61 O61 Fe2 135.93(10) . . yes
O61 C61 C66 117.91(15) . . ?
O61 C61 C62 123.09(14) . . ?
C66 C61 C62 118.99(15) . . ?
C63 C62 C61 118.41(16) . . ?
C63 C62 C53 118.51(16) . . ?
C61 C62 C53 123.01(14) . . ?
C64 C63 C62 121.63(18) . . ?
C64 C63 H63 119.2 . . ?
C62 C63 H63 119.2 . . ?
C65 C64 C63 119.65(17) . . ?
C65 C64 H64 120.2 . . ?
C63 C64 H64 120.2 . . ?
C64 C65 C66 120.23(17) . . ?
C64 C65 H65 119.9 . . ?
C66 C65 H65 119.9 . . ?
C65 C66 C61 121.04(18) . . ?
C65 C66 H66 119.5 . . ?
C61 C66 H66 119.5 . . ?
N71 C71 H711 109.5 . . ?
N71 C71 H712 109.5 . . ?
H711 C71 H712 109.5 . . ?
N71 C71 H713 109.5 . . ?
H711 C71 H713 109.5 . . ?
H712 C71 H713 109.5 . . ?
C75 N71 N72 111.21(14) . . yes
C75 N71 C71 127.73(15) . . yes
N72 N71 C71 120.95(14) . . yes
C73 N72 N71 105.71(13) . . yes
C73 N72 Fe2 128.47(10) . . yes
N71 N72 Fe2 125.42(10) . . yes
N72 C73 C74 109.65(15) . . ?
N72 C73 C82 122.32(13) . . ?
C74 C73 C82 127.94(15) . . ?
C75 C74 C73 105.47(15) . . ?
C75 C74 H74 127.3 . . ?
C73 C74 H74 127.3 . . ?
N71 C75 C74 107.97(15) . . ?
N71 C75 H75 126.0 . . ?
C74 C75 H75 126.0 . . ?
C81 O81 Fe2 135.69(10) . . yes
O81 C81 C86 118.44(15) . . ?
O81 C81 C82 122.97(14) . . ?
C86 C81 C82 118.59(15) . . ?
C83 C82 C81 118.71(16) . . ?
C83 C82 C73 118.25(15) . . ?
C81 C82 C73 122.97(14) . . ?
C84 C83 C82 121.69(18) . . ?
C84 C83 H83 119.2 . . ?
C82 C83 H83 119.2 . . ?
C83 C84 C85 119.61(17) . . ?
C83 C84 H84 120.2 . . ?
C85 C84 H84 120.2 . . ?
C86 C85 C84 120.30(18) . . ?
C86 C85 H85 119.9 . . ?
C84 C85 H85 119.9 . . ?
C85 C86 C81 120.97(17) . . ?
C85 C86 H86 119.5 . . ?
C81 C86 H86 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 N12 C13 -0.28(18) . . . . ?
C11 N11 N12 C13 176.33(15) . . . . ?
C15 N11 N12 Fe1 -169.00(11) . . . . yes
C11 N11 N12 Fe1 7.6(2) . . . . yes
N11 N12 C13 C14 -0.07(17) . . . . ?
Fe1 N12 C13 C14 168.30(11) . . . . yes
N11 N12 C13 C22 178.54(13) . . . . ?
Fe1 N12 C13 C22 -13.1(2) . . . . yes
N12 C13 C14 C15 0.37(18) . . . . ?
C22 C13 C14 C15 -178.13(15) . . . . ?
N12 N11 C15 C14 0.53(19) . . . . ?
C11 N11 C15 C14 -175.76(16) . . . . ?
C13 C14 C15 N11 -0.54(19) . . . . ?
Fe1 O21 C21 C22 10.9(2) . . . . yes
Fe1 O21 C21 C26 -171.16(11) . . . . yes
O21 C21 C22 C23 179.82(15) . . . . ?
C26 C21 C22 C23 1.9(2) . . . . ?
O21 C21 C22 C13 1.5(2) . . . . ?
C26 C21 C22 C13 -176.36(14) . . . . ?
N12 C13 C22 C23 -177.26(15) . . . . ?
C14 C13 C22 C23 1.1(2) . . . . ?
N12 C13 C22 C21 1.0(2) . . . . ?
C14 C13 C22 C21 179.36(15) . . . . ?
C21 C22 C23 C24 -1.5(3) . . . . ?
C13 C22 C23 C24 176.88(16) . . . . ?
C22 C23 C24 C25 0.2(3) . . . . ?
C23 C24 C25 C26 0.7(3) . . . . ?
C24 C25 C26 C21 -0.2(3) . . . . ?
O21 C21 C26 C25 -179.16(15) . . . . ?
C22 C21 C26 C25 -1.2(2) . . . . ?
C35 N31 N32 C33 -0.90(17) . . . . ?
C31 N31 N32 C33 179.14(13) . . . . ?
C35 N31 N32 Fe1 -170.80(11) . . . . yes
C31 N31 N32 Fe1 9.24(19) . . . . yes
N31 N32 C33 C34 0.75(17) . . . . ?
Fe1 N32 C33 C34 170.25(11) . . . . yes
N31 N32 C33 C42 -177.95(13) . . . . ?
Fe1 N32 C33 C42 -8.5(2) . . . . yes
N32 C33 C34 C35 -0.34(18) . . . . ?
C42 C33 C34 C35 178.29(15) . . . . ?
N32 N31 C35 C34 0.70(19) . . . . ?
C31 N31 C35 C34 -179.34(15) . . . . ?
C33 C34 C35 N31 -0.21(19) . . . . ?
O1 Fe1 O41 C41 77.53(15) . . . . ?
O21 Fe1 O41 C41 -103.73(15) . . . . ?
N32 Fe1 O41 C41 -14.20(15) . . . . ?
N12 Fe1 O41 C41 172.06(15) . . . . ?
Fe1 O41 C41 C42 13.4(2) . . . . yes
Fe1 O41 C41 C46 -167.18(12) . . . . yes
O41 C41 C42 C43 176.95(14) . . . . ?
C46 C41 C42 C43 -2.4(2) . . . . ?
O41 C41 C42 C33 -4.0(2) . . . . ?
C46 C41 C42 C33 176.66(14) . . . . ?
N32 C33 C42 C43 -178.25(15) . . . . ?
C34 C33 C42 C43 3.3(2) . . . . ?
N32 C33 C42 C41 2.7(2) . . . . ?
C34 C33 C42 C41 -175.79(16) . . . . ?
C41 C42 C43 C44 1.6(2) . . . . ?
C33 C42 C43 C44 -177.48(16) . . . . ?
C42 C43 C44 C45 0.0(3) . . . . ?
C43 C44 C45 C46 -0.9(3) . . . . ?
C44 C45 C46 C41 0.1(3) . . . . ?
O41 C41 C46 C45 -177.78(15) . . . . ?
C42 C41 C46 C45 1.6(2) . . . . ?
C55 N51 N52 C53 -1.28(17) . . . . ?
C51 N51 N52 C53 178.38(14) . . . . ?
C55 N51 N52 Fe2 -173.29(11) . . . . yes
C51 N51 N52 Fe2 6.4(2) . . . . yes
N51 N52 C53 C54 0.91(17) . . . . ?
Fe2 N52 C53 C54 172.62(11) . . . . yes
N51 N52 C53 C62 -179.85(14) . . . . ?
Fe2 N52 C53 C62 -8.1(2) . . . . yes
N52 C53 C54 C55 -0.23(18) . . . . ?
C62 C53 C54 C55 -179.42(15) . . . . ?
N52 N51 C55 C54 1.16(19) . . . . ?
C51 N51 C55 C54 -178.47(15) . . . . ?
C53 C54 C55 N51 -0.55(19) . . . . ?
O1 Fe2 O61 C61 75.62(16) . . . . ?
O81 Fe2 O61 C61 -106.87(15) . . . . ?
N52 Fe2 O61 C61 -15.72(15) . . . . ?
N72 Fe2 O61 C61 169.78(15) . . . . ?
Fe2 O61 C61 C62 10.3(2) . . . . yes
Fe2 O61 C61 C66 -171.22(12) . . . . yes
O61 C61 C62 C63 -179.25(15) . . . . ?
C66 C61 C62 C63 2.3(2) . . . . ?
O61 C61 C62 C53 3.7(2) . . . . ?
C66 C61 C62 C53 -174.80(15) . . . . ?
N52 C53 C62 C63 179.46(15) . . . . ?
C54 C53 C62 C63 -1.4(3) . . . . ?
N52 C53 C62 C61 -3.5(2) . . . . ?
C54 C53 C62 C61 175.64(16) . . . . ?
C61 C62 C63 C64 -1.7(3) . . . . ?
C53 C62 C63 C64 175.47(16) . . . . ?
C62 C63 C64 C65 -0.4(3) . . . . ?
C63 C64 C65 C66 2.0(3) . . . . ?
C64 C65 C66 C61 -1.4(3) . . . . ?
O61 C61 C66 C65 -179.31(15) . . . . ?
C62 C61 C66 C65 -0.8(2) . . . . ?
C75 N71 N72 C73 -0.14(18) . . . . ?
C71 N71 N72 C73 176.22(14) . . . . ?
C75 N71 N72 Fe2 -173.37(11) . . . . yes
C71 N71 N72 Fe2 3.0(2) . . . . yes
N71 N72 C73 C74 0.22(17) . . . . ?
Fe2 N72 C73 C74 173.18(11) . . . . yes
N71 N72 C73 C82 -176.48(14) . . . . ?
Fe2 N72 C73 C82 -3.5(2) . . . . yes
N72 C73 C74 C75 -0.22(18) . . . . ?
C82 C73 C74 C75 176.25(16) . . . . ?
N72 N71 C75 C74 0.01(19) . . . . ?
C71 N71 C75 C74 -176.05(16) . . . . ?
C73 C74 C75 N71 0.13(19) . . . . ?
Fe2 O81 C81 C82 23.4(2) . . . . yes
Fe2 O81 C81 C86 -157.61(13) . . . . yes
O81 C81 C82 C83 175.06(16) . . . . ?
C86 C81 C82 C83 -3.9(2) . . . . ?
O81 C81 C82 C73 -8.2(2) . . . . ?
C86 C81 C82 C73 172.82(15) . . . . ?
N72 C73 C82 C83 176.71(16) . . . . ?
C74 C73 C82 C83 0.6(3) . . . . ?
N72 C73 C82 C81 -0.1(2) . . . . ?
C74 C73 C82 C81 -176.12(16) . . . . ?
C81 C82 C83 C84 3.1(3) . . . . ?
C73 C82 C83 C84 -173.79(19) . . . . ?
C82 C83 C84 C85 0.3(3) . . . . ?
C83 C84 C85 C86 -2.8(4) . . . . ?
C84 C85 C86 C81 1.9(3) . . . . ?
O81 C81 C86 C85 -177.52(18) . . . . ?
C82 C81 C86 C85 1.5(3) . . . . ?

_refine_diff_density_max         0.416
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.065

_shelxl_version_number           2014/6

