# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_S3
_database_code_depnum_ccdc_archive 'CCDC 1509670'
_audit_update_record             
;
2016-10-13 deposited with the CCDC.
2017-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H40 Cl4 Fe4 N8 O8, 2(O)'
_chemical_formula_sum            'C36 H40 Cl4 Fe4 N8 O10'
_chemical_formula_weight         1109.96

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'
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      tetragonal
_space_group_IT_number           114
_space_group_name_H-M_alt        'P -4 21 c'
_space_group_name_Hall           'P -4 2n'

_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, z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+1/2, z+1/2'

_cell_length_a                   11.0842(13)
_cell_length_b                   11.0842(13)
_cell_length_c                   18.299(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2248.2(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    20304
_cell_measurement_theta_min      2.14
_cell_measurement_theta_max      27.11

_exptl_crystal_description       Rhombic
_exptl_crystal_colour            Black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.565
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_T_max  0.799
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18840
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.148
_diffrn_reflns_theta_max         26.832
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2411
_reflns_number_gt                2076
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0816P)²+2.8397P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 853 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2411
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1505
_refine_ls_wR_factor_gt          0.1315
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.145
_refine_ls_shift/su_max          0.000
_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 -0.65468(9) -0.47109(9) -0.94192(5) 0.0362(3) Uani 1 1 d . . . . .
Cl1 Cl -0.7822(2) -0.2998(2) -0.95598(12) 0.0620(6) Uani 1 1 d . . . . .
O1 O -0.4815(4) -0.3786(4) -0.9473(2) 0.0361(10) Uani 1 1 d . . . . .
O2 O -0.7915(6) -0.5946(6) -0.9301(4) 0.0643(16) Uani 1 1 d . . . . .
H2B H -0.8547 -0.5654 -0.9452 0.096 Uiso 1 1 calc R U . . .
N1 N -0.6166(5) -0.4242(5) -0.8336(3) 0.0364(12) Uani 1 1 d . . . . .
C8 C -0.5385(6) -0.3354(6) -0.8269(4) 0.0383(13) Uani 1 1 d . . . . .
C1 C -0.6578(7) -0.4479(6) -0.7639(4) 0.0423(15) Uani 1 1 d . . . . .
N2 N -0.5258(6) -0.2987(5) -0.7574(3) 0.0413(13) Uani 1 1 d . . . . .
C6 C -0.6017(8) -0.3712(7) -0.7153(4) 0.0481(18) Uani 1 1 d . . . . .
C9 C -0.4712(7) -0.2895(7) -0.8919(4) 0.0416(15) Uani 1 1 d . . . . .
H9A H -0.5056 -0.2138 -0.9084 0.050 Uiso 1 1 calc R U . . .
H9B H -0.3871 -0.2763 -0.8796 0.050 Uiso 1 1 calc R U . . .
C7 C -0.4460(9) -0.2030(8) -0.7309(5) 0.062(2) Uani 1 1 d . . . . .
H7A H -0.3642 -0.2217 -0.7439 0.093 Uiso 1 1 calc R U . . .
H7B H -0.4527 -0.1969 -0.6787 0.093 Uiso 1 1 calc R U . . .
H7C H -0.4688 -0.1277 -0.7528 0.093 Uiso 1 1 calc R U . . .
C2 C -0.7401(8) -0.5345(8) -0.7402(5) 0.055(2) Uani 1 1 d . . . . .
H2A H -0.7788 -0.5864 -0.7725 0.066 Uiso 1 1 calc R U . . .
C5 C -0.6234(12) -0.3753(10) -0.6412(5) 0.077(3) Uani 1 1 d . . . . .
H5 H -0.5863 -0.3223 -0.6089 0.092 Uiso 1 1 calc R U . . .
C3 C -0.7608(11) -0.5387(10) -0.6660(6) 0.078(3) Uani 1 1 d . . . . .
H3 H -0.8154 -0.5947 -0.6475 0.093 Uiso 1 1 calc R U . . .
C4 C -0.7021(13) -0.4611(10) -0.6180(6) 0.087(4) Uani 1 1 d . . . . .
H4 H -0.7172 -0.4683 -0.5682 0.104 Uiso 1 1 calc R U . . .
O1W O -1.0000 -0.5000 -0.979(3) 0.35(2) Uani 1 2 d S T P . .


_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 O2 2.054(7) . ?
Fe1 O1 2.063(5) 4_453 ?
Fe1 N1 2.092(6) . ?
Fe1 O1 2.179(5) . ?
Fe1 O1 2.251(5) 2_445 ?
Fe1 Cl1 2.381(2) . ?
O1 C9 1.420(8) . ?
O1 Fe1 2.063(5) 3_543 ?
O1 Fe1 2.251(5) 2_445 ?
O2 H2B 0.8200 . ?
N1 C8 1.317(9) . ?
N1 C1 1.379(9) . ?
C8 N2 1.343(8) . ?
C8 C9 1.492(10) . ?
C1 C6 1.379(11) . ?
C1 C2 1.394(11) . ?
N2 C6 1.395(10) . ?
N2 C7 1.464(10) . ?
C6 C5 1.378(11) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C2 C3 1.378(13) . ?
C2 H2A 0.9300 . ?
C5 C4 1.359(17) . ?
C5 H5 0.9300 . ?
C3 C4 1.391(17) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?

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
O2 Fe1 O1 101.4(2) . 4_453 ?
O2 Fe1 N1 102.4(2) . . ?
O1 Fe1 N1 155.3(2) 4_453 . ?
O2 Fe1 O1 165.7(2) . . ?
O1 Fe1 O1 79.9(2) 4_453 . ?
N1 Fe1 O1 75.44(19) . . ?
O2 Fe1 O1 90.4(2) . 2_445 ?
O1 Fe1 O1 78.20(19) 4_453 2_445 ?
N1 Fe1 O1 95.19(19) . 2_445 ?
O1 Fe1 O1 75.86(19) . 2_445 ?
O2 Fe1 Cl1 96.00(18) . . ?
O1 Fe1 Cl1 92.55(14) 4_453 . ?
N1 Fe1 Cl1 91.38(17) . . ?
O1 Fe1 Cl1 98.21(15) . . ?
O1 Fe1 Cl1 169.69(13) 2_445 . ?
C9 O1 Fe1 125.0(4) . 3_543 ?
C9 O1 Fe1 111.4(4) . . ?
Fe1 O1 Fe1 100.26(19) 3_543 . ?
C9 O1 Fe1 115.4(4) . 2_445 ?
Fe1 O1 Fe1 97.94(19) 3_543 2_445 ?
Fe1 O1 Fe1 103.90(19) . 2_445 ?
Fe1 O2 H2B 109.5 . . ?
C8 N1 C1 105.9(6) . . ?
C8 N1 Fe1 114.0(4) . . ?
C1 N1 Fe1 139.6(5) . . ?
N1 C8 N2 112.5(6) . . ?
N1 C8 C9 120.6(6) . . ?
N2 C8 C9 126.8(6) . . ?
C6 C1 N1 109.3(7) . . ?
C6 C1 C2 121.3(7) . . ?
N1 C1 C2 129.5(7) . . ?
C8 N2 C6 106.6(6) . . ?
C8 N2 C7 126.6(7) . . ?
C6 N2 C7 126.8(7) . . ?
C5 C6 C1 122.4(9) . . ?
C5 C6 N2 131.9(9) . . ?
C1 C6 N2 105.7(6) . . ?
O1 C9 C8 107.0(6) . . ?
O1 C9 H9A 110.3 . . ?
C8 C9 H9A 110.3 . . ?
O1 C9 H9B 110.3 . . ?
C8 C9 H9B 110.3 . . ?
H9A C9 H9B 108.6 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C2 C1 116.1(9) . . ?
C3 C2 H2A 122.0 . . ?
C1 C2 H2A 122.0 . . ?
C4 C5 C6 116.3(10) . . ?
C4 C5 H5 121.9 . . ?
C6 C5 H5 121.9 . . ?
C2 C3 C4 121.5(10) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 122.4(9) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?

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
C1 N1 C8 N2 -0.3(8) . . . . ?
Fe1 N1 C8 N2 173.2(5) . . . . ?
C1 N1 C8 C9 177.3(7) . . . . ?
Fe1 N1 C8 C9 -9.2(8) . . . . ?
C8 N1 C1 C6 -0.2(8) . . . . ?
Fe1 N1 C1 C6 -171.1(5) . . . . ?
C8 N1 C1 C2 -178.9(8) . . . . ?
Fe1 N1 C1 C2 10.2(13) . . . . ?
N1 C8 N2 C6 0.7(8) . . . . ?
C9 C8 N2 C6 -176.7(7) . . . . ?
N1 C8 N2 C7 179.5(7) . . . . ?
C9 C8 N2 C7 2.1(12) . . . . ?
N1 C1 C6 C5 -178.9(8) . . . . ?
C2 C1 C6 C5 0.0(13) . . . . ?
N1 C1 C6 N2 0.7(8) . . . . ?
C2 C1 C6 N2 179.5(7) . . . . ?
C8 N2 C6 C5 178.6(10) . . . . ?
C7 N2 C6 C5 -0.1(15) . . . . ?
C8 N2 C6 C1 -0.8(8) . . . . ?
C7 N2 C6 C1 -179.6(7) . . . . ?
Fe1 O1 C9 C8 153.9(4) 3_543 . . . ?
Fe1 O1 C9 C8 33.4(7) . . . . ?
Fe1 O1 C9 C8 -84.8(6) 2_445 . . . ?
N1 C8 C9 O1 -16.9(9) . . . . ?
N2 C8 C9 O1 160.3(7) . . . . ?
C6 C1 C2 C3 -0.4(12) . . . . ?
N1 C1 C2 C3 178.2(8) . . . . ?
C1 C6 C5 C4 1.2(15) . . . . ?
N2 C6 C5 C4 -178.2(9) . . . . ?
C1 C2 C3 C4 -0.3(15) . . . . ?
C6 C5 C4 C3 -1.9(19) . . . . ?
C2 C3 C4 C5 1.5(19) . . . . ?

_refine_diff_density_max         0.610
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.115

####################################################################### 
# 
# 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_S2
_database_code_depnum_ccdc_archive 'CCDC 1509669'
_audit_update_record             
;
2016-10-13 deposited with the CCDC.
2017-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H40 Cl4 Fe4 N8 O8, 2(O)'
_chemical_formula_sum            'C36 H40 Cl4 Fe4 N8 O10'
_chemical_formula_weight         1109.96

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'
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      tetragonal
_space_group_IT_number           114
_space_group_name_H-M_alt        'P -4 21 c'
_space_group_name_Hall           'P -4 2n'

_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'
'y, -x, -z'
'-x, -y, z'
'-y, x, -z'
'x+1/2, -y+1/2, -z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'y+1/2, x+1/2, z+1/2'

_cell_length_a                   10.96009(19)
_cell_length_b                   10.96009(19)
_cell_length_c                   18.3921(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2209.32(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    31754
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      29.96

_exptl_crystal_description       Rhombic
_exptl_crystal_colour            Black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.593
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.731
_exptl_absorpt_correction_T_max  0.796
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30350
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.163
_diffrn_reflns_theta_max         29.958
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3142
_reflns_number_gt                2691
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.995

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0517P)²+3.2222P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.03(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3142
_refine_ls_number_parameters     144
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.102
_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 -0.65450(6) -0.47115(7) -0.94201(4) 0.02991(18) Uani 1 1 d . . . . .
Cl1 Cl -0.78259(15) -0.29867(16) -0.95610(9) 0.0525(4) Uani 1 1 d . . . . .
O1 O -0.4811(3) -0.3774(3) -0.94721(19) 0.0301(7) Uani 1 1 d . . . . .
O2 O -0.7914(5) -0.5930(5) -0.9307(3) 0.0573(12) Uani 1 1 d . . . . .
H2 H -0.7902 -0.6409 -0.9649 0.086 Uiso 1 1 calc R U . . .
C8 C -0.5390(5) -0.3344(5) -0.8273(3) 0.0316(9) Uani 1 1 d D . . . .
C1 C -0.6588(5) -0.4477(5) -0.7642(3) 0.0351(11) Uani 1 1 d . . . . .
N1 N -0.6171(4) -0.4240(4) -0.8338(2) 0.0303(8) Uani 1 1 d . . . . .
N2 N -0.5262(5) -0.2986(4) -0.7576(2) 0.0351(9) Uani 1 1 d . . . . .
C6 C -0.6018(6) -0.3705(5) -0.7152(3) 0.0407(13) Uani 1 1 d . . . . .
C9 C -0.4716(5) -0.2896(5) -0.8920(3) 0.0362(11) Uani 1 1 d D . . . .
H9A H -0.5061 -0.2128 -0.9084 0.043 Uiso 1 1 calc R U . . .
H9B H -0.3866 -0.2763 -0.8798 0.043 Uiso 1 1 calc R U . . .
C2 C -0.7415(6) -0.5353(6) -0.7407(4) 0.0481(14) Uani 1 1 d . . . . .
H2A H -0.7808 -0.5877 -0.7728 0.058 Uiso 1 1 calc R U . . .
C7 C -0.4466(7) -0.2033(6) -0.7311(4) 0.0529(16) Uani 1 1 d . . . . .
H7A H -0.3665 -0.2139 -0.7513 0.079 Uiso 1 1 calc R U . . .
H7B H -0.4421 -0.2073 -0.6791 0.079 Uiso 1 1 calc R U . . .
H7C H -0.4783 -0.1252 -0.7454 0.079 Uiso 1 1 calc R U . . .
C3 C -0.7618(9) -0.5394(8) -0.6662(5) 0.069(2) Uani 1 1 d . . . . .
H3 H -0.8165 -0.5964 -0.6478 0.083 Uiso 1 1 calc R U . . .
C4 C -0.7029(10) -0.4608(8) -0.6185(4) 0.075(3) Uani 1 1 d . . . . .
H4 H -0.7189 -0.4678 -0.5690 0.091 Uiso 1 1 calc R U . . .
C5 C -0.6239(9) -0.3752(7) -0.6408(4) 0.065(2) Uani 1 1 d . . . . .
H5 H -0.5861 -0.3221 -0.6084 0.077 Uiso 1 1 calc R U . . .
O1W O 0.0000 0.5000 0.023(2) 0.281(16) Uani 1 2 d S T P . .


_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 O2 2.019(5) . ?
Fe1 O1 2.070(4) 4_453 ?
Fe1 N1 2.097(4) . ?
Fe1 O1 2.162(3) . ?
Fe1 O1 2.230(4) 3_445 ?
Fe1 Cl1 2.3689(17) . ?
O1 C9 1.403(6) . ?
O1 Fe1 2.070(4) 2_543 ?
O1 Fe1 2.230(4) 3_445 ?
O2 H2 0.8200 . ?
C8 N1 1.308(7) . ?
C8 N2 1.347(6) . ?
C8 C9 1.485(7) . ?
C1 N1 1.384(7) . ?
C1 C6 1.385(8) . ?
C1 C2 1.389(9) . ?
N2 C6 1.384(8) . ?
N2 C7 1.446(7) . ?
C6 C5 1.391(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C2 C3 1.388(11) . ?
C2 H2A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C3 C4 1.390(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.341(13) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?

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
O2 Fe1 O1 101.1(2) . 4_453 ?
O2 Fe1 N1 102.13(19) . . ?
O1 Fe1 N1 156.09(16) 4_453 . ?
O2 Fe1 O1 166.33(17) . . ?
O1 Fe1 O1 80.38(16) 4_453 . ?
N1 Fe1 O1 75.71(15) . . ?
O2 Fe1 O1 90.44(16) . 3_445 ?
O1 Fe1 O1 78.80(15) 4_453 3_445 ?
N1 Fe1 O1 95.37(15) . 3_445 ?
O1 Fe1 O1 76.45(14) . 3_445 ?
O2 Fe1 Cl1 95.66(14) . . ?
O1 Fe1 Cl1 91.99(10) 4_453 . ?
N1 Fe1 Cl1 91.33(13) . . ?
O1 Fe1 Cl1 97.87(11) . . ?
O1 Fe1 Cl1 169.81(11) 3_445 . ?
C9 O1 Fe1 126.3(3) . 2_543 ?
C9 O1 Fe1 111.0(3) . . ?
Fe1 O1 Fe1 99.80(15) 2_543 . ?
C9 O1 Fe1 115.5(3) . 3_445 ?
Fe1 O1 Fe1 97.64(15) 2_543 3_445 ?
Fe1 O1 Fe1 103.32(14) . 3_445 ?
Fe1 O2 H2 109.5 . . ?
N1 C8 N2 111.9(5) . . ?
N1 C8 C9 120.0(4) . . ?
N2 C8 C9 127.9(5) . . ?
N1 C1 C6 109.8(5) . . ?
N1 C1 C2 129.3(6) . . ?
C6 C1 C2 120.9(5) . . ?
C8 N1 C1 105.8(4) . . ?
C8 N1 Fe1 113.6(3) . . ?
C1 N1 Fe1 140.1(4) . . ?
C8 N2 C6 107.9(5) . . ?
C8 N2 C7 126.4(5) . . ?
C6 N2 C7 125.7(5) . . ?
N2 C6 C1 104.6(5) . . ?
N2 C6 C5 132.8(7) . . ?
C1 C6 C5 122.6(7) . . ?
O1 C9 C8 108.5(4) . . ?
O1 C9 H9A 110.0 . . ?
C8 C9 H9A 110.0 . . ?
O1 C9 H9B 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
C3 C2 C1 115.7(7) . . ?
C3 C2 H2A 122.1 . . ?
C1 C2 H2A 122.1 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C3 C4 121.9(7) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 122.8(7) . . ?
C5 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
C4 C5 C6 116.0(8) . . ?
C4 C5 H5 122.0 . . ?
C6 C5 H5 122.0 . . ?

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
N2 C8 N1 C1 0.5(6) . . . . ?
C9 C8 N1 C1 177.0(5) . . . . ?
N2 C8 N1 Fe1 173.9(3) . . . . ?
C9 C8 N1 Fe1 -9.6(6) . . . . ?
C6 C1 N1 C8 -0.9(6) . . . . ?
C2 C1 N1 C8 -179.0(6) . . . . ?
C6 C1 N1 Fe1 -171.4(4) . . . . ?
C2 C1 N1 Fe1 10.5(10) . . . . ?
N1 C8 N2 C6 0.0(6) . . . . ?
C9 C8 N2 C6 -176.1(5) . . . . ?
N1 C8 N2 C7 179.3(5) . . . . ?
C9 C8 N2 C7 3.1(9) . . . . ?
C8 N2 C6 C1 -0.6(6) . . . . ?
C7 N2 C6 C1 -179.8(5) . . . . ?
C8 N2 C6 C5 178.9(7) . . . . ?
C7 N2 C6 C5 -0.4(11) . . . . ?
N1 C1 C6 N2 0.9(6) . . . . ?
C2 C1 C6 N2 179.2(5) . . . . ?
N1 C1 C6 C5 -178.6(6) . . . . ?
C2 C1 C6 C5 -0.3(9) . . . . ?
Fe1 O1 C9 C8 153.5(3) 2_543 . . . ?
Fe1 O1 C9 C8 32.9(5) . . . . ?
Fe1 O1 C9 C8 -84.3(5) 3_445 . . . ?
N1 C8 C9 O1 -16.3(7) . . . . ?
N2 C8 C9 O1 159.6(5) . . . . ?
N1 C1 C2 C3 177.8(6) . . . . ?
C6 C1 C2 C3 -0.2(9) . . . . ?
C1 C2 C3 C4 0.0(11) . . . . ?
C2 C3 C4 C5 0.7(15) . . . . ?
C3 C4 C5 C6 -1.2(14) . . . . ?
N2 C6 C5 C4 -178.4(7) . . . . ?
C1 C6 C5 C4 1.0(11) . . . . ?

_refine_diff_density_max         0.626
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.098

####################################################################### 
# 
# 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_S1
_database_code_depnum_ccdc_archive 'CCDC 1509668'
_audit_update_record             
;
2016-10-13 deposited with the CCDC.
2017-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H52 Cl4 Fe4 N8 O8'
_chemical_formula_sum            'C40 H52 Cl4 Fe4 N8 O8'
_chemical_formula_weight         1138.09

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'
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      tetragonal
_space_group_IT_number           114
_space_group_name_H-M_alt        'P -4 21 c'
_space_group_name_Hall           'P -4 2n'

_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'
'y, -x, -z'
'-x, -y, z'
'-y, x, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+1/2, z+1/2'

_cell_length_a                   11.148(2)
_cell_length_b                   11.148(2)
_cell_length_c                   19.893(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2472.3(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    39130
_cell_measurement_theta_min      2.047
_cell_measurement_theta_max      31.069

_exptl_crystal_description       Rhombic
_exptl_crystal_colour            'Light Yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.422
_shelx_estimated_absorpt_T_min   0.718
_shelx_estimated_absorpt_T_max   0.815
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.718
_exptl_absorpt_correction_T_max  0.815
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37744
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.1078
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.047
_diffrn_reflns_theta_max         31.069
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3821
_reflns_number_gt                3548
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_max     0.947
_reflns_Friedel_fraction_full    1.000

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.1870P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1458 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3821
_refine_ls_number_parameters     151
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0819
_refine_ls_wR_factor_gt          0.0800
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.070
_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 -0.64819(3) -0.48147(3) -0.94571(2) 0.03190(10) Uani 1 1 d . . . . .
Cl1 Cl -0.81857(6) -0.61265(7) -0.93594(4) 0.05189(18) Uani 1 1 d . . . . .
O1 O -0.48465(15) -0.37502(14) -0.94917(8) 0.0326(3) Uani 1 1 d . . . . .
N1 N -0.62110(19) -0.4267(2) -0.84368(11) 0.0370(4) Uani 1 1 d . . . . .
C8 C -0.5463(2) -0.3355(2) -0.83849(12) 0.0356(5) Uani 1 1 d D . . . .
O1M O -0.7550(2) -0.3197(3) -0.95925(14) 0.0623(6) Uani 1 1 d D . . . .
N2 N -0.5351(2) -0.2967(2) -0.77373(12) 0.0405(4) Uani 1 1 d . . . . .
C1 C -0.6606(2) -0.4517(2) -0.77907(12) 0.0381(5) Uani 1 1 d . . . . .
C7 C -0.4599(3) -0.2008(3) -0.74942(16) 0.0539(7) Uani 1 1 d . . . . .
H7A H -0.3909 -0.2340 -0.7274 0.081 Uiso 1 1 calc R U . . .
H7B H -0.5043 -0.1525 -0.7181 0.081 Uiso 1 1 calc R U . . .
H7C H -0.4345 -0.1520 -0.7866 0.081 Uiso 1 1 calc R U . . .
C6 C -0.6074(3) -0.3700(3) -0.73473(13) 0.0414(5) Uani 1 1 d . . . . .
C1M C -0.8736(4) -0.2979(5) -0.9467(3) 0.0917(16) Uani 1 1 d . . . . .
H1MA H -0.9216 -0.3346 -0.9811 0.138 Uiso 1 1 calc R U . . .
H1MB H -0.8876 -0.2129 -0.9465 0.138 Uiso 1 1 calc R U . . .
H1MC H -0.8949 -0.3309 -0.9037 0.138 Uiso 1 1 calc R U . . .
C9 C -0.4803(2) -0.2876(2) -0.89835(12) 0.0386(5) Uani 1 1 d D . . . .
H9A H -0.5175 -0.2140 -0.9138 0.046 Uiso 1 1 calc R U . . .
H9B H -0.3977 -0.2705 -0.8865 0.046 Uiso 1 1 calc R U . . .
C2 C -0.7372(3) -0.5408(3) -0.75600(15) 0.0488(7) Uani 1 1 d . . . . .
H2 H -0.7733 -0.5950 -0.7852 0.059 Uiso 1 1 calc R U . . .
C5 C -0.6288(3) -0.3741(3) -0.66599(15) 0.0575(8) Uani 1 1 d . . . . .
H5 H -0.5940 -0.3194 -0.6366 0.069 Uiso 1 1 calc R U . . .
C3 C -0.7571(3) -0.5453(4) -0.68724(18) 0.0633(9) Uani 1 1 d . . . . .
H3 H -0.8069 -0.6046 -0.6699 0.076 Uiso 1 1 calc R U . . .
C4 C -0.7046(4) -0.4634(4) -0.64363(16) 0.0696(11) Uani 1 1 d . . . . .
H4 H -0.7211 -0.4690 -0.5979 0.084 Uiso 1 1 calc R U . . .
H1M H -0.733(4) -0.278(4) -0.9880(18) 0.079(15) Uiso 1 1 d D . . . .


_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 O1 2.1073(16) 4_453 ?
Fe1 N1 2.141(2) . ?
Fe1 O1 2.1764(17) . ?
Fe1 O1M 2.178(2) . ?
Fe1 O1 2.1810(17) 3_445 ?
Fe1 Cl1 2.4051(8) . ?
O1 C9 1.405(3) . ?
O1 Fe1 2.1074(16) 2_543 ?
O1 Fe1 2.1811(18) 3_445 ?
N1 C8 1.319(3) . ?
N1 C1 1.387(3) . ?
C8 N2 1.365(3) . ?
C8 C9 1.498(3) . ?
O1M C1M 1.367(4) . ?
O1M H1M 0.77(2) . ?
N2 C6 1.385(4) . ?
N2 C7 1.442(4) . ?
C1 C2 1.388(4) . ?
C1 C6 1.400(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C6 C5 1.389(4) . ?
C1M H1MA 0.9600 . ?
C1M H1MB 0.9600 . ?
C1M H1MC 0.9600 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C2 C3 1.387(4) . ?
C2 H2 0.9300 . ?
C5 C4 1.380(6) . ?
C5 H5 0.9300 . ?
C3 C4 1.388(6) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?

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
O1 Fe1 N1 158.16(8) 4_453 . ?
O1 Fe1 O1 82.81(7) 4_453 . ?
N1 Fe1 O1 75.90(7) . . ?
O1 Fe1 O1M 87.61(9) 4_453 . ?
N1 Fe1 O1M 87.62(10) . . ?
O1 Fe1 O1M 90.16(9) . . ?
O1 Fe1 O1 82.70(7) 4_453 3_445 ?
N1 Fe1 O1 98.24(7) . 3_445 ?
O1 Fe1 O1 80.22(7) . 3_445 ?
O1M Fe1 O1 167.10(8) . 3_445 ?
O1 Fe1 Cl1 99.61(5) 4_453 . ?
N1 Fe1 Cl1 102.01(6) . . ?
O1 Fe1 Cl1 174.67(5) . . ?
O1M Fe1 Cl1 94.67(8) . . ?
O1 Fe1 Cl1 95.33(5) 3_445 . ?
C9 O1 Fe1 128.93(15) . 2_543 ?
C9 O1 Fe1 112.59(14) . . ?
Fe1 O1 Fe1 96.46(6) 2_543 . ?
C9 O1 Fe1 117.56(15) . 3_445 ?
Fe1 O1 Fe1 96.32(7) 2_543 3_445 ?
Fe1 O1 Fe1 99.66(7) . 3_445 ?
C8 N1 C1 106.4(2) . . ?
C8 N1 Fe1 112.53(17) . . ?
C1 N1 Fe1 140.95(18) . . ?
N1 C8 N2 112.1(2) . . ?
N1 C8 C9 121.5(2) . . ?
N2 C8 C9 126.3(2) . . ?
C1M O1M Fe1 130.8(3) . . ?
C1M O1M H1M 109(3) . . ?
Fe1 O1M H1M 114(3) . . ?
C8 N2 C6 106.7(2) . . ?
C8 N2 C7 127.2(3) . . ?
C6 N2 C7 126.0(2) . . ?
N1 C1 C2 130.2(2) . . ?
N1 C1 C6 108.6(2) . . ?
C2 C1 C6 121.2(2) . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C6 C5 132.1(3) . . ?
N2 C6 C1 106.1(2) . . ?
C5 C6 C1 121.7(3) . . ?
O1M C1M H1MA 109.5 . . ?
O1M C1M H1MB 109.5 . . ?
H1MA C1M H1MB 109.5 . . ?
O1M C1M H1MC 109.5 . . ?
H1MA C1M H1MC 109.5 . . ?
H1MB C1M H1MC 109.5 . . ?
O1 C9 C8 107.9(2) . . ?
O1 C9 H9A 110.1 . . ?
C8 C9 H9A 110.1 . . ?
O1 C9 H9B 110.1 . . ?
C8 C9 H9B 110.1 . . ?
H9A C9 H9B 108.4 . . ?
C3 C2 C1 116.8(3) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
C4 C5 C6 116.5(3) . . ?
C4 C5 H5 121.8 . . ?
C6 C5 H5 121.8 . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 122.1(3) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?

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
C1 N1 C8 N2 -1.0(3) . . . . ?
Fe1 N1 C8 N2 176.35(17) . . . . ?
C1 N1 C8 C9 176.7(2) . . . . ?
Fe1 N1 C8 C9 -6.0(3) . . . . ?
N1 C8 N2 C6 0.8(3) . . . . ?
C9 C8 N2 C6 -176.8(3) . . . . ?
N1 C8 N2 C7 178.8(3) . . . . ?
C9 C8 N2 C7 1.2(5) . . . . ?
C8 N1 C1 C2 -177.9(3) . . . . ?
Fe1 N1 C1 C2 6.1(5) . . . . ?
C8 N1 C1 C6 0.8(3) . . . . ?
Fe1 N1 C1 C6 -175.3(2) . . . . ?
C8 N2 C6 C5 178.3(3) . . . . ?
C7 N2 C6 C5 0.3(5) . . . . ?
C8 N2 C6 C1 -0.2(3) . . . . ?
C7 N2 C6 C1 -178.3(3) . . . . ?
N1 C1 C6 N2 -0.3(3) . . . . ?
C2 C1 C6 N2 178.5(3) . . . . ?
N1 C1 C6 C5 -179.1(3) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
Fe1 O1 C9 C8 150.99(16) 2_543 . . . ?
Fe1 O1 C9 C8 31.5(2) . . . . ?
Fe1 O1 C9 C8 -83.5(2) 3_445 . . . ?
N1 C8 C9 O1 -17.4(3) . . . . ?
N2 C8 C9 O1 159.9(2) . . . . ?
N1 C1 C2 C3 178.0(3) . . . . ?
C6 C1 C2 C3 -0.5(5) . . . . ?
N2 C6 C5 C4 -177.8(4) . . . . ?
C1 C6 C5 C4 0.5(5) . . . . ?
C1 C2 C3 C4 1.0(6) . . . . ?
C6 C5 C4 C3 0.0(7) . . . . ?
C2 C3 C4 C5 -0.7(7) . . . . ?

_refine_diff_density_max         0.609
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.074

