# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2013664'
loop_
_audit_author_name
_audit_author_address
'Shouvik Chattopadhyay'
;Jadavpur University, kolkata
India
;
_audit_update_record             
;
2020-07-02 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H36 Cl Fe N6 O4 Se2'
_chemical_formula_weight         745.83

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'
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'
Se Se -0.0929 2.2259 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   24.0615(8)
_cell_length_b                   14.0088(8)
_cell_length_c                   10.0527(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.996(4)
_cell_angle_gamma                90
_cell_volume                     3326.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    900
_cell_measurement_theta_min      2.06
_cell_measurement_theta_max      22.58

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_F_000             1508
_exptl_transmission_factor_min   0.665
_exptl_transmission_factor_max   0.857
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.761
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER SMART APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20491
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.690
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_full        25.048
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2913
_reflns_number_gt                2412
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1260P)²+18.7922P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2913
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0651
_refine_ls_wR_factor_ref         0.2214
_refine_ls_wR_factor_gt          0.2095
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_refine_ls_shift/su_max          0.042
_refine_ls_shift/su_mean         0.009

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
Cl1 Cl 0.500000 0.7624(3) 0.750000 0.0957(14) Uani 1 2 d S T P . .
Fe1 Fe 0.750000 0.750000 0.500000 0.0263(3) Uani 1 2 d S . P . .
Se1 Se 0.88585(4) 0.85971(6) 0.90407(8) 0.0625(4) Uani 1 1 d . . . . .
O2 O 0.81251(16) 0.6638(3) 0.4821(4) 0.0328(9) Uani 1 1 d . . . . .
O1 O 0.88314(19) 0.5693(3) 0.3594(5) 0.0451(11) Uani 1 1 d . . . . .
N1 N 0.72684(19) 0.6520(3) 0.6396(5) 0.0287(10) Uani 1 1 d . . . . .
N3 N 0.8031(2) 0.8214(4) 0.6624(5) 0.0360(11) Uani 1 1 d . . . . .
N2 N 0.5824(2) 0.7442(4) 0.5469(6) 0.0454(14) Uani 1 1 d . . . . .
H2A H 0.563665 0.763180 0.610438 0.054 Uiso 1 1 calc R U . . .
H2B H 0.613497 0.779866 0.554568 0.054 Uiso 1 1 calc R U . . .
C7 C 0.8124(2) 0.5690(4) 0.4898(5) 0.0287(12) Uani 1 1 d . . . . .
C8 C 0.7427(2) 0.5645(4) 0.6454(6) 0.0329(13) Uani 1 1 d . . . . .
H8 H 0.729399 0.526243 0.708214 0.040 Uiso 1 1 calc R U . . .
C2 C 0.8492(2) 0.5155(4) 0.4252(6) 0.0325(13) Uani 1 1 d . . . . .
C6 C 0.7790(2) 0.5187(4) 0.5651(6) 0.0323(12) Uani 1 1 d . . . . .
C13 C 0.8344(3) 0.8347(4) 0.7539(8) 0.0400(15) Uani 1 1 d . . . . .
C9 C 0.6910(3) 0.6817(5) 0.7368(6) 0.0368(13) Uani 1 1 d . . . . .
H9A H 0.684801 0.750030 0.729326 0.044 Uiso 1 1 calc R U . . .
H9B H 0.710850 0.668206 0.828181 0.044 Uiso 1 1 calc R U . . .
C10 C 0.6338(3) 0.6313(5) 0.7132(7) 0.0478(17) Uani 1 1 d . . . . .
H10A H 0.640091 0.563665 0.730595 0.057 Uiso 1 1 calc R U . . .
H10B H 0.612124 0.655331 0.777971 0.057 Uiso 1 1 calc R U . . .
C5 C 0.7817(3) 0.4176(4) 0.5732(7) 0.0437(15) Uani 1 1 d . . . . .
H5 H 0.759724 0.384759 0.624950 0.052 Uiso 1 1 calc R U . . .
C3 C 0.8506(3) 0.4177(5) 0.4326(7) 0.0444(15) Uani 1 1 d . . . . .
H3A H 0.874945 0.383874 0.388268 0.053 Uiso 1 1 calc R U . . .
C11 C 0.5993(3) 0.6436(5) 0.5724(8) 0.0472(17) Uani 1 1 d . . . . .
H11A H 0.6220(12) 0.6226(13) 0.505(4) 0.057 Uiso 1 1 calc R U . . .
H11B H 0.5649(19) 0.603(2) 0.5617(11) 0.057 Uiso 1 1 calc R U . . .
C4 C 0.8163(3) 0.3689(5) 0.5053(8) 0.0488(17) Uani 1 1 d . . . . .
H4 H 0.817019 0.302571 0.507719 0.059 Uiso 1 1 calc R U . . .
C1 C 0.9207(3) 0.5196(6) 0.2900(9) 0.060(2) Uani 1 1 d . . . . .
H1A H 0.944565 0.478127 0.352219 0.090 Uiso 1 1 calc R U . . .
H1B H 0.943655 0.564681 0.252979 0.090 Uiso 1 1 calc R U . . .
H1C H 0.899130 0.482366 0.217951 0.090 Uiso 1 1 calc R U . . .
C12 C 0.5473(4) 0.7609(8) 0.4149(9) 0.075(3) Uani 1 1 d . . . . .
H12A H 0.569641 0.753130 0.346018 0.113 Uiso 1 1 calc R U . . .
H12B H 0.532431 0.824626 0.411182 0.113 Uiso 1 1 calc R U . . .
H12C H 0.516622 0.715977 0.400044 0.113 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 O2 1.963(4) 7_666 ?
Fe1 O2 1.963(4) . ?
Fe1 N1 2.113(4) . ?
Fe1 N1 2.113(4) 7_666 ?
Fe1 N3 2.122(6) . ?
Fe1 N3 2.122(6) 7_666 ?
Se1 C13 1.794(8) . ?
O2 C7 1.331(7) . ?
O1 C2 1.371(7) . ?
O1 C1 1.425(7) . ?
N1 C8 1.281(7) . ?
N1 C9 1.482(7) . ?
N3 C13 1.088(9) . ?
N2 C12 1.450(11) . ?
N2 C11 1.475(8) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
C7 C6 1.396(8) . ?
C7 C2 1.410(8) . ?
C8 C6 1.448(8) . ?
C8 H8 0.9300 . ?
C2 C3 1.372(8) . ?
C6 C5 1.419(8) . ?
C9 C10 1.522(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.508(11) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C5 C4 1.358(9) . ?
C5 H5 0.9300 . ?
C3 C4 1.383(9) . ?
C3 H3A 0.9300 . ?
C11 H11A 1.00(5) . ?
C11 H11B 1.00(5) . ?
C4 H4 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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 O2 180.0 7_666 . ?
O2 Fe1 N1 92.02(16) 7_666 . ?
O2 Fe1 N1 87.98(16) . . ?
O2 Fe1 N1 87.98(16) 7_666 7_666 ?
O2 Fe1 N1 92.02(16) . 7_666 ?
N1 Fe1 N1 180.0 . 7_666 ?
O2 Fe1 N3 89.95(18) 7_666 . ?
O2 Fe1 N3 90.05(18) . . ?
N1 Fe1 N3 89.54(19) . . ?
N1 Fe1 N3 90.46(19) 7_666 . ?
O2 Fe1 N3 90.05(18) 7_666 7_666 ?
O2 Fe1 N3 89.95(18) . 7_666 ?
N1 Fe1 N3 90.45(19) . 7_666 ?
N1 Fe1 N3 89.55(19) 7_666 7_666 ?
N3 Fe1 N3 180.0 . 7_666 ?
C7 O2 Fe1 126.7(3) . . ?
C2 O1 C1 117.3(5) . . ?
C8 N1 C9 116.4(5) . . ?
C8 N1 Fe1 122.6(4) . . ?
C9 N1 Fe1 121.1(4) . . ?
C13 N3 Fe1 161.6(5) . . ?
C12 N2 C11 113.9(7) . . ?
C12 N2 H2A 108.8 . . ?
C11 N2 H2A 108.8 . . ?
C12 N2 H2B 108.8 . . ?
C11 N2 H2B 108.8 . . ?
H2A N2 H2B 107.7 . . ?
O2 C7 C6 122.9(5) . . ?
O2 C7 C2 119.7(5) . . ?
C6 C7 C2 117.3(5) . . ?
N1 C8 C6 127.2(5) . . ?
N1 C8 H8 116.4 . . ?
C6 C8 H8 116.4 . . ?
O1 C2 C3 124.4(5) . . ?
O1 C2 C7 114.5(5) . . ?
C3 C2 C7 121.1(5) . . ?
C7 C6 C5 120.7(5) . . ?
C7 C6 C8 123.3(5) . . ?
C5 C6 C8 115.8(5) . . ?
N3 C13 Se1 178.5(6) . . ?
N1 C9 C10 112.9(5) . . ?
N1 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
N1 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 114.4(5) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C4 C5 C6 119.8(6) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C2 C3 C4 120.7(6) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
N2 C11 C10 110.9(6) . . ?
N2 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C5 C4 C3 120.2(6) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         3.149
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.171

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2013665'
loop_
_audit_author_name
_audit_author_address
'Shouvik Chattopadhyay'
;Jadavpur University, kolkata
India
;
_audit_update_record             
;
2020-07-02 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H34 Cl Fe N4 O6'
_chemical_formula_weight         565.85

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'
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'
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'
S S 0.1246 0.1234 '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                   9.866(9)
_cell_length_b                   10.754(9)
_cell_length_c                   13.600(12)
_cell_angle_alpha                96.95(2)
_cell_angle_beta                 108.18(2)
_cell_angle_gamma                109.27(2)
_cell_volume                     1253.2(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    900
_cell_measurement_theta_min      2.06
_cell_measurement_theta_max      25.87

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BLACK
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_F_000             594
_exptl_transmission_factor_min   0.669
_exptl_transmission_factor_max   0.875
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.756
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8 QUEST area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8064
_diffrn_reflns_av_unetI/netI     0.1240
_diffrn_reflns_av_R_equivalents  0.0825
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.072
_diffrn_reflns_theta_max         24.895
_diffrn_reflns_theta_full        24.895
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measured_fraction_theta_full 0.917
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_Laue_measured_fraction_full 0.917
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.917
_reflns_number_total             4000
_reflns_number_gt                2323
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1592P)²+7.7791P] 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         4000
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1737
_refine_ls_R_factor_gt           0.1045
_refine_ls_wR_factor_ref         0.3419
_refine_ls_wR_factor_gt          0.2757
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.43209(14) 0.74328(14) 0.22597(11) 0.0462(5) Uani 1 1 d . . . . .
O1 O 0.2493(7) 0.6594(7) 0.2494(6) 0.0507(18) Uani 1 1 d . . . . .
O5 O 0.0101(7) 0.4951(7) 0.2723(6) 0.0557(19) Uani 1 1 d . . . . .
N1 N 0.4609(9) 0.9214(8) 0.2959(7) 0.049(2) Uani 1 1 d . . . . .
N3 N 0.2966(9) 0.7449(9) 0.0779(7) 0.043(2) Uani 1 1 d . . . . .
C24 C 0.8210(14) 0.7944(14) 0.6642(10) 0.083(4) Uani 1 1 d . . . . .
H24A H 0.849477 0.887111 0.699945 0.125 Uiso 1 1 calc R U . . .
H24B H 0.764091 0.734551 0.697333 0.125 Uiso 1 1 calc R U . . .
H24C H 0.912739 0.778405 0.669174 0.125 Uiso 1 1 calc R U . . .
O2 O 0.5594(7) 0.7385(6) 0.3583(5) 0.0476(17) Uani 1 1 d . . . . .
C6 C 0.2639(11) 0.8486(11) 0.3692(8) 0.050(3) Uani 1 1 d . . . . .
N2 N 0.6280(8) 0.8432(8) 0.2000(7) 0.043(2) Uani 1 1 d . . . . .
N4 N 0.4029(8) 0.5676(8) 0.1561(6) 0.046(2) Uani 1 1 d . . . . .
C11 C 0.2004(10) 0.7141(11) 0.3157(8) 0.050(3) Uani 1 1 d . . . . .
C7 C 0.1985(13) 0.8949(13) 0.4378(9) 0.062(3) Uani 1 1 d . . . . .
H7 H 0.241090 0.986204 0.473971 0.074 Uiso 1 1 calc R U . . .
C8 C 0.0755(12) 0.8078(13) 0.4512(9) 0.064(3) Uani 1 1 d . . . . .
H8 H 0.034810 0.840259 0.496965 0.077 Uiso 1 1 calc R U . . .
C9 C 0.0085(12) 0.6723(12) 0.3990(8) 0.058(3) Uani 1 1 d . . . . .
H9 H -0.075646 0.613345 0.409858 0.069 Uiso 1 1 calc R U . . .
C10 C 0.0686(10) 0.6242(11) 0.3291(8) 0.050(3) Uani 1 1 d . . . . .
C12 C -0.1227(14) 0.4009(13) 0.2831(11) 0.080(4) Uani 1 1 d . . . . .
H12A H -0.152652 0.312555 0.238430 0.121 Uiso 1 1 calc R U . . .
H12B H -0.097936 0.395959 0.356289 0.121 Uiso 1 1 calc R U . . .
H12C H -0.206567 0.430818 0.262005 0.121 Uiso 1 1 calc R U . . .
C5 C 0.3906(11) 0.9485(11) 0.3552(9) 0.053(3) Uani 1 1 d . . . . .
H5 H 0.423685 1.038653 0.391598 0.064 Uiso 1 1 calc R U . . .
C4 C 0.5817(11) 1.0292(10) 0.2829(9) 0.053(3) Uani 1 1 d . . . . .
H4A H 0.625210 1.108119 0.342764 0.063 Uiso 1 1 calc R U . . .
H4B H 0.540327 1.055393 0.217805 0.063 Uiso 1 1 calc R U . . .
C3 C 0.7080(11) 0.9773(11) 0.2774(9) 0.059(3) Uani 1 1 d . . . . .
H3A H 0.780607 1.039843 0.254170 0.071 Uiso 1 1 calc R U . . .
H3B H 0.764512 0.969063 0.347148 0.071 Uiso 1 1 calc R U . . .
C2 C 0.7351(11) 0.7724(12) 0.2078(10) 0.063(3) Uani 1 1 d . . . . .
H2A H 0.676896 0.682179 0.159921 0.075 Uiso 1 1 calc R U . . .
H2B H 0.769543 0.760918 0.279895 0.075 Uiso 1 1 calc R U . . .
C1 C 0.8762(12) 0.8383(13) 0.1829(10) 0.064(3) Uani 1 1 d . . . . .
H1A H 0.919040 0.935511 0.214187 0.077 Uiso 1 1 calc R U . . .
H1B H 0.953652 0.803487 0.215767 0.077 Uiso 1 1 calc R U . . .
O3 O 0.8457(13) 0.8160(13) 0.0749(9) 0.105(4) Uani 1 1 d . . . . .
H3O H 0.829515 0.879827 0.053665 0.158 Uiso 1 1 calc R U . . .
C15 C 0.2083(12) 0.5964(11) 0.0178(8) 0.057(3) Uani 1 1 d . . . . .
H15A H 0.126350 0.553448 0.042523 0.068 Uiso 1 1 calc R U . . .
H15B H 0.162477 0.588055 -0.058210 0.068 Uiso 1 1 calc R U . . .
C16 C 0.3217(12) 0.5319(12) 0.0394(8) 0.060(3) Uani 1 1 d . . . . .
H16A H 0.269314 0.433981 0.012034 0.072 Uiso 1 1 calc R U . . .
H16B H 0.394652 0.565266 0.005255 0.072 Uiso 1 1 calc R U . . .
C17 C 0.4391(11) 0.4768(11) 0.2029(9) 0.055(3) Uani 1 1 d . . . . .
H17 H 0.405555 0.389745 0.160370 0.066 Uiso 1 1 calc R U . . .
C18 C 0.5249(11) 0.5015(11) 0.3124(9) 0.050(3) Uani 1 1 d . . . . .
C23 C 0.5827(10) 0.6302(10) 0.3839(9) 0.046(2) Uani 1 1 d . . . . .
C22 C 0.6756(11) 0.6447(11) 0.4916(9) 0.052(3) Uani 1 1 d . . . . .
O6 O 0.7276(8) 0.7696(8) 0.5556(6) 0.064(2) Uani 1 1 d . . . . .
C21 C 0.7028(12) 0.5350(13) 0.5240(10) 0.062(3) Uani 1 1 d . . . . .
H21 H 0.762463 0.545707 0.595012 0.074 Uiso 1 1 calc R U . . .
C20 C 0.6429(13) 0.4107(12) 0.4528(10) 0.061(3) Uani 1 1 d . . . . .
H20 H 0.660394 0.337633 0.476276 0.074 Uiso 1 1 calc R U . . .
C19 C 0.5589(12) 0.3936(12) 0.3492(10) 0.061(3) Uani 1 1 d . . . . .
H19 H 0.522814 0.309839 0.301277 0.073 Uiso 1 1 calc R U . . .
C14 C 0.1913(12) 0.8164(12) 0.0738(9) 0.059(3) Uani 1 1 d . . . . .
H14A H 0.252632 0.909402 0.116071 0.070 Uiso 1 1 calc R U . . .
H14B H 0.121207 0.773613 0.107569 0.070 Uiso 1 1 calc R U . . .
C13 C 0.0960(14) 0.8202(16) -0.0354(10) 0.079(4) Uani 1 1 d . . . . .
H13A H 0.020870 0.728936 -0.074174 0.095 Uiso 1 1 calc R U . . .
H13B H 0.039324 0.876876 -0.027824 0.095 Uiso 1 1 calc R U . . .
O4 O 0.1851(12) 0.8702(12) -0.0949(8) 0.097(3) Uani 1 1 d . . . . .
H4O H 0.270365 0.926817 -0.054562 0.145 Uiso 1 1 calc R U . . .
Cl1 Cl 0.5414(4) 0.8311(4) -0.0555(3) 0.0785(10) Uani 1 1 d . . . . .
H2 H 0.604(9) 0.865(8) 0.143(6) 0.02(2) Uiso 1 1 d . . . . .
H3 H 0.356(13) 0.735(12) 0.059(9) 0.06(4) 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 O2 1.864(7) . ?
Fe1 O1 1.877(7) . ?
Fe1 N4 1.895(8) . ?
Fe1 N1 1.920(9) . ?
Fe1 N2 2.040(8) . ?
Fe1 N3 2.046(8) . ?
O1 C11 1.311(12) . ?
O5 C10 1.339(12) . ?
O5 C12 1.430(13) . ?
N1 C5 1.282(14) . ?
N1 C4 1.437(13) . ?
N3 C14 1.475(13) . ?
N3 C15 1.516(13) . ?
C24 O6 1.413(13) . ?
O2 C23 1.325(11) . ?
C6 C11 1.370(14) . ?
C6 C7 1.418(15) . ?
C6 C5 1.436(15) . ?
N2 C3 1.474(13) . ?
N2 C2 1.480(14) . ?
N4 C17 1.313(13) . ?
N4 C16 1.471(13) . ?
C11 C10 1.421(14) . ?
C7 C8 1.346(16) . ?
C8 C9 1.374(16) . ?
C9 C10 1.399(15) . ?
C4 C3 1.542(16) . ?
C2 C1 1.501(15) . ?
C1 O3 1.377(15) . ?
C15 C16 1.475(15) . ?
C17 C18 1.405(15) . ?
C18 C23 1.412(14) . ?
C18 C19 1.415(15) . ?
C23 C22 1.422(14) . ?
C22 O6 1.345(13) . ?
C22 C21 1.386(15) . ?
C21 C20 1.372(17) . ?
C20 C19 1.347(15) . ?
C14 C13 1.503(15) . ?
C13 O4 1.398(15) . ?

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 93.5(3) . . ?
O2 Fe1 N4 94.2(3) . . ?
O1 Fe1 N4 87.2(3) . . ?
O2 Fe1 N1 86.2(3) . . ?
O1 Fe1 N1 92.8(3) . . ?
N4 Fe1 N1 179.6(4) . . ?
O2 Fe1 N2 87.9(3) . . ?
O1 Fe1 N2 177.0(3) . . ?
N4 Fe1 N2 95.3(4) . . ?
N1 Fe1 N2 84.6(4) . . ?
O2 Fe1 N3 177.7(4) . . ?
O1 Fe1 N3 87.8(3) . . ?
N4 Fe1 N3 84.1(4) . . ?
N1 Fe1 N3 95.5(4) . . ?
N2 Fe1 N3 90.8(4) . . ?
C11 O1 Fe1 126.5(6) . . ?
C10 O5 C12 117.9(9) . . ?
C5 N1 C4 120.2(9) . . ?
C5 N1 Fe1 126.2(8) . . ?
C4 N1 Fe1 113.5(7) . . ?
C14 N3 C15 111.5(8) . . ?
C14 N3 Fe1 117.1(7) . . ?
C15 N3 Fe1 105.1(6) . . ?
C23 O2 Fe1 126.0(6) . . ?
C11 C6 C7 119.5(10) . . ?
C11 C6 C5 123.0(10) . . ?
C7 C6 C5 117.4(10) . . ?
C3 N2 C2 110.2(8) . . ?
C3 N2 Fe1 107.0(6) . . ?
C2 N2 Fe1 115.6(6) . . ?
C17 N4 C16 119.7(9) . . ?
C17 N4 Fe1 126.0(7) . . ?
C16 N4 Fe1 114.1(7) . . ?
O1 C11 C6 125.2(9) . . ?
O1 C11 C10 115.7(9) . . ?
C6 C11 C10 119.1(10) . . ?
C8 C7 C6 120.6(11) . . ?
C7 C8 C9 121.6(11) . . ?
C8 C9 C10 119.0(11) . . ?
O5 C10 C9 124.0(9) . . ?
O5 C10 C11 115.9(9) . . ?
C9 C10 C11 120.1(10) . . ?
N1 C5 C6 124.2(10) . . ?
N1 C4 C3 108.1(9) . . ?
N2 C3 C4 106.7(8) . . ?
N2 C2 C1 117.4(10) . . ?
O3 C1 C2 113.1(10) . . ?
C16 C15 N3 106.5(8) . . ?
N4 C16 C15 106.9(9) . . ?
N4 C17 C18 124.8(10) . . ?
C17 C18 C23 122.3(10) . . ?
C17 C18 C19 117.6(10) . . ?
C23 C18 C19 120.0(10) . . ?
O2 C23 C18 125.3(9) . . ?
O2 C23 C22 117.7(9) . . ?
C18 C23 C22 117.0(9) . . ?
O6 C22 C21 125.2(10) . . ?
O6 C22 C23 114.2(9) . . ?
C21 C22 C23 120.6(10) . . ?
C22 O6 C24 118.6(9) . . ?
C20 C21 C22 120.8(11) . . ?
C19 C20 C21 120.6(11) . . ?
C20 C19 C18 120.9(11) . . ?
N3 C14 C13 116.4(10) . . ?
O4 C13 C14 113.0(10) . . ?

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
O2 Fe1 O1 C11 71.6(8) . . . . ?
N4 Fe1 O1 C11 165.6(8) . . . . ?
N1 Fe1 O1 C11 -14.7(8) . . . . ?
N3 Fe1 O1 C11 -110.2(8) . . . . ?
O1 Fe1 O2 C23 76.6(8) . . . . ?
N4 Fe1 O2 C23 -10.9(8) . . . . ?
N1 Fe1 O2 C23 169.1(8) . . . . ?
N2 Fe1 O2 C23 -106.1(8) . . . . ?
O2 Fe1 N4 C17 12.7(9) . . . . ?
O1 Fe1 N4 C17 -80.7(8) . . . . ?
N2 Fe1 N4 C17 100.9(9) . . . . ?
N3 Fe1 N4 C17 -168.8(9) . . . . ?
O2 Fe1 N4 C16 -171.9(7) . . . . ?
O1 Fe1 N4 C16 94.7(7) . . . . ?
N2 Fe1 N4 C16 -83.7(7) . . . . ?
N3 Fe1 N4 C16 6.6(7) . . . . ?
Fe1 O1 C11 C6 9.3(15) . . . . ?
Fe1 O1 C11 C10 -172.2(6) . . . . ?
C7 C6 C11 O1 179.3(10) . . . . ?
C5 C6 C11 O1 2.6(16) . . . . ?
C7 C6 C11 C10 0.9(15) . . . . ?
C5 C6 C11 C10 -175.8(9) . . . . ?
C11 C6 C7 C8 0.3(17) . . . . ?
C5 C6 C7 C8 177.3(10) . . . . ?
C6 C7 C8 C9 -0.4(18) . . . . ?
C7 C8 C9 C10 -0.8(17) . . . . ?
C12 O5 C10 C9 0.4(15) . . . . ?
C12 O5 C10 C11 -179.9(10) . . . . ?
C8 C9 C10 O5 -178.3(9) . . . . ?
C8 C9 C10 C11 2.1(16) . . . . ?
O1 C11 C10 O5 -0.3(13) . . . . ?
C6 C11 C10 O5 178.3(9) . . . . ?
O1 C11 C10 C9 179.3(9) . . . . ?
C6 C11 C10 C9 -2.1(15) . . . . ?
C4 N1 C5 C6 177.0(9) . . . . ?
Fe1 N1 C5 C6 -7.7(14) . . . . ?
C11 C6 C5 N1 -3.3(16) . . . . ?
C7 C6 C5 N1 179.9(10) . . . . ?
C5 N1 C4 C3 143.1(9) . . . . ?
Fe1 N1 C4 C3 -32.8(9) . . . . ?
C2 N2 C3 C4 -167.2(9) . . . . ?
Fe1 N2 C3 C4 -40.8(10) . . . . ?
N1 C4 C3 N2 48.3(11) . . . . ?
C3 N2 C2 C1 -62.1(13) . . . . ?
Fe1 N2 C2 C1 176.5(8) . . . . ?
N2 C2 C1 O3 -80.0(14) . . . . ?
C14 N3 C15 C16 -172.6(9) . . . . ?
Fe1 N3 C15 C16 -44.9(10) . . . . ?
C17 N4 C16 C15 141.5(10) . . . . ?
Fe1 N4 C16 C15 -34.2(11) . . . . ?
N3 C15 C16 N4 51.3(11) . . . . ?
C16 N4 C17 C18 175.8(10) . . . . ?
Fe1 N4 C17 C18 -9.0(15) . . . . ?
N4 C17 C18 C23 -0.6(17) . . . . ?
N4 C17 C18 C19 -177.6(10) . . . . ?
Fe1 O2 C23 C18 5.6(13) . . . . ?
Fe1 O2 C23 C22 -175.5(7) . . . . ?
C17 C18 C23 O2 2.5(16) . . . . ?
C19 C18 C23 O2 179.5(9) . . . . ?
C17 C18 C23 C22 -176.4(9) . . . . ?
C19 C18 C23 C22 0.6(14) . . . . ?
O2 C23 C22 O6 0.7(13) . . . . ?
C18 C23 C22 O6 179.7(9) . . . . ?
O2 C23 C22 C21 179.1(10) . . . . ?
C18 C23 C22 C21 -1.9(15) . . . . ?
C21 C22 O6 C24 1.7(16) . . . . ?
C23 C22 O6 C24 180.0(10) . . . . ?
O6 C22 C21 C20 179.2(10) . . . . ?
C23 C22 C21 C20 1.0(17) . . . . ?
C22 C21 C20 C19 1.4(18) . . . . ?
C21 C20 C19 C18 -2.8(17) . . . . ?
C17 C18 C19 C20 178.9(10) . . . . ?
C23 C18 C19 C20 1.7(16) . . . . ?
C15 N3 C14 C13 -60.7(13) . . . . ?
Fe1 N3 C14 C13 178.3(8) . . . . ?
N3 C14 C13 O4 -53.2(16) . . . . ?

_refine_diff_density_max         1.072
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.128

