# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_compound(1)
_database_code_depnum_ccdc_archive 'CCDC 2253225'
_audit_update_record             
;
2023-03-31 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'Manganese-organic Compound'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 Mn0.50 N4 O3'
_chemical_formula_weight         351.81

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'
Mn Mn 0.3368 0.7283 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.9293(7)
_cell_length_b                   8.5740(7)
_cell_length_c                   11.9825(10)
_cell_angle_alpha                81.591(2)
_cell_angle_beta                 88.173(2)
_cell_angle_gamma                89.232(2)
_cell_volume                     805.44(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3523
_cell_measurement_theta_min      2.401
_cell_measurement_theta_max      27.074

_exptl_crystal_description       Parallelogram-shaped
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             365
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.020
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.011
_exptl_absorpt_coefficient_mu    0.470
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26234
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.401
_diffrn_reflns_theta_max         27.074
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3523
_reflns_number_gt                3013
_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       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1999) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'
_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)+(0.0002P)²+1.3986P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3523
_refine_ls_number_parameters     287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_ref         0.1152
_refine_ls_wR_factor_gt          0.1100
_refine_ls_goodness_of_fit_ref   1.225
_refine_ls_restrained_S_all      1.225
_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
Mn1 Mn 0.500000 0.500000 0.500000 0.02009(18) Uani 1 2 d S . P . .
O3 O 0.5900(4) 0.3359(3) 0.6467(2) 0.0326(6) Uani 1 1 d . . . . .
O1 O 0.2493(3) 0.4192(3) 0.5483(2) 0.0351(6) Uani 1 1 d . . . . .
N1 N 0.5188(4) 0.3064(3) 0.3865(2) 0.0272(6) Uani 1 1 d . . . . .
O2 O 0.2745(3) 0.2740(3) 0.7164(2) 0.0506(8) Uani 1 1 d . . . . .
N3 N 0.7675(4) 0.4739(4) 0.8115(3) 0.0418(8) Uani 1 1 d . . . . .
N2 N 0.5188(4) 0.0544(4) 0.0370(2) 0.0392(8) Uani 1 1 d . . . . .
C3 C 0.0071(4) 0.1288(4) 0.5607(3) 0.0285(8) Uani 1 1 d . . . . .
C8 C 0.4958(5) 0.1044(4) 0.2259(3) 0.0294(8) Uani 1 1 d . . . . .
N4 N 0.9856(5) 0.9467(4) 0.9616(3) 0.0556(10) Uani 1 1 d . . . . .
C7 C 0.5946(5) 0.2381(4) 0.2055(3) 0.0334(9) Uani 1 1 d . . . . .
C4 C -0.0843(5) 0.1374(4) 0.4640(3) 0.0350(9) Uani 1 1 d . . . . .
C1 C 0.1931(4) 0.3252(4) 0.6313(3) 0.0311(8) Uani 1 1 d . . . . .
C6 C 0.6010(5) 0.3349(4) 0.2867(3) 0.0315(8) Uani 1 1 d . . . . .
C5 C 0.0921(5) -0.0108(4) 0.5958(3) 0.0348(9) Uani 1 1 d . . . . .
C10 C 0.4315(5) 0.1730(4) 0.4073(3) 0.0337(8) Uani 1 1 d . . . . .
C11 C 0.4719(5) 0.0054(4) 0.1371(3) 0.0340(9) Uani 1 1 d . . . . .
C2 C 0.0132(5) 0.2674(5) 0.6259(4) 0.0369(9) Uani 1 1 d . . . . .
C9 C 0.4162(5) 0.0689(4) 0.3305(3) 0.0337(8) Uani 1 1 d . . . . .
C14 C 0.8622(5) 0.7033(4) 0.9403(3) 0.0363(9) Uani 1 1 d . . . . .
C15 C 0.9124(6) 0.7107(5) 0.8285(4) 0.0452(10) Uani 1 1 d . . . . .
C16 C 0.8620(6) 0.5955(5) 0.7680(4) 0.0481(11) Uani 1 1 d . . . . .
C12 C 0.7220(6) 0.4655(5) 0.9195(4) 0.0503(11) Uani 1 1 d . . . . .
C17 C 0.9063(5) 0.8263(5) 1.0075(3) 0.0420(10) Uani 1 1 d . . . . .
C13 C 0.7654(6) 0.5765(5) 0.9866(3) 0.0473(11) Uani 1 1 d . . . . .
H3B H 0.639(5) 0.370(4) 0.694(3) 0.035(12) Uiso 1 1 d . . . . .
H3A H 0.491(6) 0.311(5) 0.679(4) 0.061(15) Uiso 1 1 d . . . . .
H5 H 0.153(4) -0.017(4) 0.661(3) 0.034(10) Uiso 1 1 d . . . . .
H2A H -0.053(5) 0.350(4) 0.590(3) 0.036(11) Uiso 1 1 d . . . . .
H4 H -0.142(5) 0.225(5) 0.437(3) 0.050(12) Uiso 1 1 d . . . . .
H2B H -0.036(5) 0.235(5) 0.703(4) 0.064(14) Uiso 1 1 d . . . . .
H16 H 0.891(5) 0.602(4) 0.691(3) 0.048(12) Uiso 1 1 d . . . . .
H15 H 0.971(5) 0.791(5) 0.792(3) 0.057(13) Uiso 1 1 d . . . . .
H13 H 0.729(5) 0.568(5) 1.061(4) 0.063(14) Uiso 1 1 d . . . . .
H12 H 0.654(5) 0.382(5) 0.952(4) 0.063(14) Uiso 1 1 d . . . . .
H6 H 0.668(4) 0.425(4) 0.274(3) 0.033(10) Uiso 1 1 d . . . . .
H9 H 0.354(5) -0.019(4) 0.350(3) 0.038(11) Uiso 1 1 d . . . . .
H10 H 0.379(4) 0.153(4) 0.480(3) 0.038(10) Uiso 1 1 d . . . . .
H7 H 0.653(5) 0.267(4) 0.136(3) 0.048(12) Uiso 1 1 d . . . . .
H17 H 0.874(5) 0.812(4) 1.082(3) 0.038(11) Uiso 1 1 d . . . . .
H11 H 0.418(5) -0.091(5) 0.158(3) 0.049(12) Uiso 1 1 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
Mn1 O1 2.148(2) 2_666 ?
Mn1 O1 2.148(2) . ?
Mn1 O3 2.215(3) . ?
Mn1 O3 2.215(3) 2_666 ?
Mn1 N1 2.295(3) 2_666 ?
Mn1 N1 2.295(3) . ?
O3 H3B 0.79(4) . ?
O3 H3A 0.88(5) . ?
O1 C1 1.259(4) . ?
N1 C10 1.333(4) . ?
N1 C6 1.336(4) . ?
O2 C1 1.246(4) . ?
N3 C12 1.324(5) . ?
N3 C16 1.325(5) . ?
N2 C11 1.258(4) . ?
N2 N2 1.418(5) 2_655 ?
C3 C4 1.379(5) . ?
C3 C5 1.383(5) . ?
C3 C2 1.517(5) . ?
C8 C9 1.380(5) . ?
C8 C7 1.385(5) . ?
C8 C11 1.473(4) . ?
N4 C17 1.262(5) . ?
N4 N4 1.414(6) 2_777 ?
C7 C6 1.371(5) . ?
C7 H7 0.94(4) . ?
C4 C5 1.388(5) 2_556 ?
C4 H4 0.89(4) . ?
C1 C2 1.523(5) . ?
C6 H6 0.94(3) . ?
C5 H5 0.93(4) . ?
C10 C9 1.382(5) . ?
C10 H10 0.95(4) . ?
C11 H11 0.94(4) . ?
C2 H2A 0.93(4) . ?
C2 H2B 1.00(4) . ?
C9 H9 0.91(4) . ?
C14 C13 1.378(5) . ?
C14 C15 1.378(5) . ?
C14 C17 1.470(5) . ?
C15 C16 1.379(5) . ?
C15 H15 0.89(4) . ?
C16 H16 0.94(4) . ?
C12 C13 1.386(6) . ?
C12 H12 0.93(4) . ?
C17 H17 0.91(4) . ?
C13 H13 0.92(4) . ?

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 Mn1 O1 180.0 2_666 . ?
O1 Mn1 O3 92.51(10) 2_666 . ?
O1 Mn1 O3 87.49(10) . . ?
O1 Mn1 O3 87.49(10) 2_666 2_666 ?
O1 Mn1 O3 92.51(10) . 2_666 ?
O3 Mn1 O3 180.0 . 2_666 ?
O1 Mn1 N1 87.72(9) 2_666 2_666 ?
O1 Mn1 N1 92.28(9) . 2_666 ?
O3 Mn1 N1 88.48(10) . 2_666 ?
O3 Mn1 N1 91.52(10) 2_666 2_666 ?
O1 Mn1 N1 92.28(9) 2_666 . ?
O1 Mn1 N1 87.73(9) . . ?
O3 Mn1 N1 91.52(10) . . ?
O3 Mn1 N1 88.48(10) 2_666 . ?
N1 Mn1 N1 180.0 2_666 . ?
Mn1 O3 H3B 119(3) . . ?
Mn1 O3 H3A 98(3) . . ?
H3B O3 H3A 104(4) . . ?
C1 O1 Mn1 131.9(2) . . ?
C10 N1 C6 116.7(3) . . ?
C10 N1 Mn1 123.1(2) . . ?
C6 N1 Mn1 119.5(2) . . ?
C12 N3 C16 116.6(3) . . ?
C11 N2 N2 111.8(4) . 2_655 ?
C4 C3 C5 117.5(3) . . ?
C4 C3 C2 121.0(3) . . ?
C5 C3 C2 121.5(3) . . ?
C9 C8 C7 118.2(3) . . ?
C9 C8 C11 120.8(3) . . ?
C7 C8 C11 120.9(3) . . ?
C17 N4 N4 112.1(4) . 2_777 ?
C6 C7 C8 119.0(3) . . ?
C6 C7 H7 119(2) . . ?
C8 C7 H7 122(2) . . ?
C3 C4 C5 121.5(4) . 2_556 ?
C3 C4 H4 121(3) . . ?
C5 C4 H4 117(3) 2_556 . ?
O2 C1 O1 124.9(3) . . ?
O2 C1 C2 117.7(3) . . ?
O1 C1 C2 117.3(3) . . ?
N1 C6 C7 123.6(3) . . ?
N1 C6 H6 117(2) . . ?
C7 C6 H6 120(2) . . ?
C3 C5 C4 121.0(3) . 2_556 ?
C3 C5 H5 118(2) . . ?
C4 C5 H5 121(2) 2_556 . ?
N1 C10 C9 123.9(3) . . ?
N1 C10 H10 115(2) . . ?
C9 C10 H10 121(2) . . ?
N2 C11 C8 119.8(3) . . ?
N2 C11 H11 122(2) . . ?
C8 C11 H11 118(2) . . ?
C3 C2 C1 111.2(3) . . ?
C3 C2 H2A 109(2) . . ?
C1 C2 H2A 109(2) . . ?
C3 C2 H2B 109(3) . . ?
C1 C2 H2B 111(3) . . ?
H2A C2 H2B 108(3) . . ?
C8 C9 C10 118.4(3) . . ?
C8 C9 H9 122(2) . . ?
C10 C9 H9 119(2) . . ?
C13 C14 C15 117.2(4) . . ?
C13 C14 C17 120.9(3) . . ?
C15 C14 C17 121.9(4) . . ?
C14 C15 C16 119.6(4) . . ?
C14 C15 H15 123(3) . . ?
C16 C15 H15 118(3) . . ?
N3 C16 C15 123.6(4) . . ?
N3 C16 H16 116(2) . . ?
C15 C16 H16 120(2) . . ?
N3 C12 C13 123.8(4) . . ?
N3 C12 H12 118(3) . . ?
C13 C12 H12 118(3) . . ?
N4 C17 C14 119.9(4) . . ?
N4 C17 H17 122(2) . . ?
C14 C17 H17 118(2) . . ?
C14 C13 C12 119.2(4) . . ?
C14 C13 H13 120(3) . . ?
C12 C13 H13 121(3) . . ?

_refine_diff_density_max         0.445
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_compound(2)
_database_code_depnum_ccdc_archive 'CCDC 2253226'
_audit_update_record             
;
2023-03-31 deposited with the CCDC.	2023-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'Iron-organic Compound'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 Fe0.50 N4 O3'
_chemical_formula_weight         352.26

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.9266(8)
_cell_length_b                   8.5888(8)
_cell_length_c                   11.8991(11)
_cell_angle_alpha                82.016(3)
_cell_angle_beta                 87.908(3)
_cell_angle_gamma                89.364(3)
_cell_volume                     801.69(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3540
_cell_measurement_theta_min      1.729
_cell_measurement_theta_max      27.251

_exptl_crystal_description       Parallelogram-shaped
_exptl_crystal_colour            Violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_F_000             366
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.530
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27067
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.729
_diffrn_reflns_theta_max         27.251
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3540
_reflns_number_gt                2930
_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       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1999) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'
_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)+(0.0247P)²+0.9152P] 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_number_reflns         3540
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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 0.500000 0.500000 0.500000 0.02502(15) Uani 1 2 d S . P . .
O3 O 0.5912(3) 0.3369(2) 0.64123(17) 0.0338(5) Uani 1 1 d . . . . .
O1 O 0.2533(2) 0.4238(2) 0.54712(16) 0.0347(5) Uani 1 1 d . . . . .
O2 O 0.2777(3) 0.2714(3) 0.71283(18) 0.0492(6) Uani 1 1 d . . . . .
N1 N 0.5193(3) 0.3126(2) 0.38830(17) 0.0285(5) Uani 1 1 d . . . . .
N3 N 0.7666(3) 0.4754(3) 0.8081(2) 0.0431(6) Uani 1 1 d . . . . .
N2 N 0.5184(3) 0.0549(3) 0.03672(19) 0.0414(6) Uani 1 1 d . . . . .
C9 C 0.0082(3) 0.1309(3) 0.5592(2) 0.0291(6) Uani 1 1 d . . . . .
C4 C 0.5932(4) 0.2421(3) 0.2057(2) 0.0354(7) Uani 1 1 d . . . . .
H4 H 0.652441 0.266231 0.136657 0.043 Uiso 1 1 calc R U . . .
C3 C 0.4973(4) 0.1068(3) 0.2271(2) 0.0318(6) Uani 1 1 d . . . . .
C5 C 0.6004(4) 0.3404(3) 0.2871(2) 0.0343(6) Uani 1 1 d . . . . .
H5 H 0.664944 0.431034 0.271009 0.041 Uiso 1 1 calc R U . . .
C11 C -0.0852(3) 0.1363(3) 0.4629(2) 0.0357(6) Uani 1 1 d . . . . .
H11 H -0.143629 0.227875 0.436572 0.043 Uiso 1 1 calc R U . . .
C7 C 0.1960(3) 0.3271(3) 0.6290(2) 0.0322(6) Uani 1 1 d . . . . .
N4 N 0.9855(4) 0.9470(3) 0.9610(2) 0.0569(8) Uani 1 1 d . . . . .
C10 C 0.0933(4) -0.0074(3) 0.5952(2) 0.0364(7) Uani 1 1 d . . . . .
H10 H 0.157233 -0.014151 0.659659 0.044 Uiso 1 1 calc R U . . .
C1 C 0.4344(4) 0.1778(3) 0.4108(2) 0.0329(6) Uani 1 1 d . . . . .
H1 H 0.382316 0.153330 0.482312 0.039 Uiso 1 1 calc R U . . .
C8 C 0.0152(4) 0.2720(4) 0.6226(3) 0.0367(7) Uani 1 1 d . . . . .
C6 C 0.4731(4) 0.0073(4) 0.1381(2) 0.0382(7) Uani 1 1 d . . . . .
C2 C 0.4195(4) 0.0724(3) 0.3336(2) 0.0360(7) Uani 1 1 d . . . . .
H2 H 0.358368 -0.019763 0.353018 0.043 Uiso 1 1 calc R U . . .
C14 C 0.8622(4) 0.7036(3) 0.9387(2) 0.0364(7) Uani 1 1 d . . . . .
C15 C 0.9115(4) 0.7121(4) 0.8258(3) 0.0474(8) Uani 1 1 d . . . . .
H15 H 0.978517 0.794608 0.791195 0.057 Uiso 1 1 calc R U . . .
C16 C 0.8602(4) 0.5970(4) 0.7646(3) 0.0473(8) Uani 1 1 d . . . . .
H16 H 0.893513 0.605409 0.688201 0.057 Uiso 1 1 calc R U . . .
C17 C 0.9063(4) 0.8271(4) 1.0073(3) 0.0426(7) Uani 1 1 d . . . . .
C12 C 0.7214(5) 0.4666(4) 0.9172(3) 0.0528(9) Uani 1 1 d . . . . .
H12 H 0.656572 0.381464 0.949818 0.063 Uiso 1 1 calc R U . . .
C13 C 0.7653(4) 0.5772(4) 0.9855(3) 0.0486(8) Uani 1 1 d . . . . .
H13 H 0.729931 0.566166 1.061586 0.058 Uiso 1 1 calc R U . . .
H8A H -0.032(4) 0.245(4) 0.694(3) 0.043(9) Uiso 1 1 d . . . . .
H8B H -0.050(4) 0.353(4) 0.585(3) 0.042(9) Uiso 1 1 d . . . . .
H17 H 0.871(4) 0.813(4) 1.084(3) 0.046(9) Uiso 1 1 d . . . . .
H6 H 0.421(4) -0.085(4) 0.160(2) 0.038(8) Uiso 1 1 d . . . . .
H3A H 0.500(5) 0.313(4) 0.673(3) 0.063(12) Uiso 1 1 d . . . . .
H3B H 0.642(5) 0.371(4) 0.687(3) 0.062(12) Uiso 1 1 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 2.1005(18) . ?
Fe1 O1 2.1005(18) 2_666 ?
Fe1 O3 2.172(2) 2_666 ?
Fe1 O3 2.173(2) . ?
Fe1 N1 2.226(2) 2_666 ?
Fe1 N1 2.226(2) . ?
O3 H3A 0.82(4) . ?
O3 H3B 0.78(4) . ?
O1 C7 1.264(3) . ?
O2 C7 1.245(3) . ?
N1 C1 1.335(3) . ?
N1 C5 1.336(3) . ?
N3 C16 1.323(4) . ?
N3 C12 1.326(4) . ?
N2 C6 1.260(4) . ?
N2 N2 1.412(4) 2_655 ?
C9 C10 1.382(4) . ?
C9 C11 1.382(4) . ?
C9 C8 1.517(4) . ?
C4 C5 1.374(3) . ?
C4 C3 1.384(4) . ?
C4 H4 0.9300 . ?
C3 C2 1.385(4) . ?
C3 C6 1.469(3) . ?
C5 H5 0.9300 . ?
C11 C10 1.387(4) 2_556 ?
C11 H11 0.9300 . ?
C7 C8 1.522(4) . ?
N4 C17 1.261(4) . ?
N4 N4 1.415(5) 2_777 ?
C10 H10 0.9300 . ?
C1 C2 1.385(3) . ?
C1 H1 0.9300 . ?
C8 H8A 0.91(3) . ?
C8 H8B 0.94(3) . ?
C6 H6 0.90(3) . ?
C2 H2 0.9300 . ?
C14 C13 1.378(4) . ?
C14 C15 1.378(4) . ?
C14 C17 1.477(4) . ?
C15 C16 1.380(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17 0.94(3) . ?
C12 C13 1.388(4) . ?
C12 H12 0.9300 . ?
C13 H13 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 O1 180.0 . 2_666 ?
O1 Fe1 O3 91.31(8) . 2_666 ?
O1 Fe1 O3 88.69(8) 2_666 2_666 ?
O1 Fe1 O3 88.69(8) . . ?
O1 Fe1 O3 91.31(8) 2_666 . ?
O3 Fe1 O3 180.00(9) 2_666 . ?
O1 Fe1 N1 91.67(7) . 2_666 ?
O1 Fe1 N1 88.33(7) 2_666 2_666 ?
O3 Fe1 N1 90.32(8) 2_666 2_666 ?
O3 Fe1 N1 89.68(8) . 2_666 ?
O1 Fe1 N1 88.33(7) . . ?
O1 Fe1 N1 91.67(7) 2_666 . ?
O3 Fe1 N1 89.68(8) 2_666 . ?
O3 Fe1 N1 90.32(8) . . ?
N1 Fe1 N1 180.0 2_666 . ?
Fe1 O3 H3A 98(3) . . ?
Fe1 O3 H3B 118(3) . . ?
H3A O3 H3B 105(4) . . ?
C7 O1 Fe1 131.76(19) . . ?
C1 N1 C5 116.8(2) . . ?
C1 N1 Fe1 122.61(17) . . ?
C5 N1 Fe1 120.05(17) . . ?
C16 N3 C12 116.6(3) . . ?
C6 N2 N2 112.1(3) . 2_655 ?
C10 C9 C11 117.5(2) . . ?
C10 C9 C8 121.8(3) . . ?
C11 C9 C8 120.7(3) . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C3 C2 117.6(2) . . ?
C4 C3 C6 121.0(3) . . ?
C2 C3 C6 121.3(3) . . ?
N1 C5 C4 123.4(2) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
C9 C11 C10 121.1(3) . 2_556 ?
C9 C11 H11 119.5 . . ?
C10 C11 H11 119.5 2_556 . ?
O2 C7 O1 124.8(2) . . ?
O2 C7 C8 117.9(3) . . ?
O1 C7 C8 117.3(3) . . ?
C17 N4 N4 111.7(3) . 2_777 ?
C9 C10 C11 121.4(3) . 2_556 ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 2_556 . ?
N1 C1 C2 123.6(2) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C9 C8 C7 111.1(2) . . ?
C9 C8 H8A 108.5(19) . . ?
C7 C8 H8A 110.6(19) . . ?
C9 C8 H8B 108.5(19) . . ?
C7 C8 H8B 109.7(19) . . ?
H8A C8 H8B 108(3) . . ?
N2 C6 C3 120.2(3) . . ?
N2 C6 H6 123.0(19) . . ?
C3 C6 H6 116.7(19) . . ?
C1 C2 C3 118.8(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C13 C14 C15 117.6(3) . . ?
C13 C14 C17 120.6(3) . . ?
C15 C14 C17 121.8(3) . . ?
C14 C15 C16 119.3(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
N3 C16 C15 123.9(3) . . ?
N3 C16 H16 118.1 . . ?
C15 C16 H16 118.1 . . ?
N4 C17 C14 119.6(3) . . ?
N4 C17 H17 122.7(19) . . ?
C14 C17 H17 117.7(19) . . ?
N3 C12 C13 123.8(3) . . ?
N3 C12 H12 118.1 . . ?
C13 C12 H12 118.1 . . ?
C14 C13 C12 118.8(3) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?

_refine_diff_density_max         0.290
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.062

