# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_300K
_database_code_depnum_ccdc_archive 'CCDC 2310296'
loop_
_audit_author_name
_audit_author_address
'Clara S. B. Gomes'
;LAQV REQUIMTE, FCT, Universidade NOVA de Lisboa
Portugal
;
_audit_update_record             
;
2023-11-25 deposited with the CCDC.	2024-04-26 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         'C22 H28 F2 Fe N4 O2, Cl O4'
_chemical_formula_sum            'C22 H28 Cl F2 Fe N4 O6'
_chemical_formula_weight         573.78

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'
F F 0.0171 0.0103 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.123(2)
_cell_length_b                   21.819(5)
_cell_length_c                   12.084(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.742(12)
_cell_angle_gamma                90
_cell_volume                     2592.8(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9688
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      25.66

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_F_000             1188
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.743
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30503
_diffrn_reflns_av_unetI/netI     0.0820
_diffrn_reflns_av_R_equivalents  0.1281
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.789
_diffrn_reflns_theta_max         25.146
_diffrn_reflns_theta_full        25.146
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4595
_reflns_number_gt                2647
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    Mercury
_computing_publication_material  'WinGX and enCIFer'
_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)+(0.0765P)²+0.2987P] 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         4595
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1547
_refine_ls_wR_factor_gt          0.1364
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 0.68127(5) 0.37665(3) 0.28392(5) 0.0475(2) Uani 1 1 d . . . . .
Cl1 Cl 0.71588(18) 0.40177(7) -0.12481(12) 0.0894(5) Uani 1 1 d . . . . .
O2 O 0.5364(3) 0.35101(13) 0.3484(3) 0.0625(8) Uani 1 1 d . . . . .
F1 F 1.1686(3) 0.23657(14) 0.7285(2) 0.0915(9) Uani 1 1 d . . . . .
F2 F 0.1325(3) 0.47060(15) 0.4928(3) 0.0976(11) Uani 1 1 d . . . . .
O1 O 0.8078(3) 0.38823(14) 0.4254(3) 0.0598(8) Uani 1 1 d . . . . .
N1 N 0.7606(3) 0.29043(15) 0.2756(3) 0.0482(9) Uani 1 1 d . . . . .
N3 N 0.6080(3) 0.46479(15) 0.2771(3) 0.0500(9) Uani 1 1 d . . . . .
N4 N 0.8189(3) 0.42323(17) 0.1971(3) 0.0502(10) Uani 1 1 d . . . . .
N2 N 0.5591(4) 0.34621(18) 0.1202(3) 0.0565(10) Uani 1 1 d . . . . .
C7 C 0.8500(4) 0.2633(2) 0.3541(4) 0.0508(11) Uani 1 1 d . . . . .
H7 H 0.874347 0.223545 0.339873 0.061 Uiso 1 1 calc R U . . .
C12 C 0.4439(4) 0.3825(2) 0.3845(4) 0.0521(11) Uani 1 1 d . . . . .
C18 C 0.5130(4) 0.4845(2) 0.3223(3) 0.0522(11) Uani 1 1 d . . . . .
H18 H 0.497686 0.526575 0.320959 0.063 Uiso 1 1 calc R U . . .
O3 O 0.7539(5) 0.3559(2) -0.0429(3) 0.1181(16) Uani 1 1 d . . . . .
C17 C 0.4285(4) 0.4465(2) 0.3751(3) 0.0481(11) Uani 1 1 d . . . . .
C6 C 0.9152(4) 0.2902(2) 0.4627(4) 0.0540(12) Uani 1 1 d . . . . .
C8 C 0.7044(5) 0.2567(2) 0.1689(4) 0.0642(13) Uani 1 1 d . . . . .
H8A H 0.706641 0.212876 0.183158 0.077 Uiso 1 1 calc R U . . .
H8B H 0.757061 0.265207 0.113261 0.077 Uiso 1 1 calc R U . . .
O4 O 0.6731(6) 0.4532(2) -0.0731(4) 0.146(2) Uani 1 1 d . . . . .
C1 C 0.8891(4) 0.3501(2) 0.4944(4) 0.0550(12) Uani 1 1 d . . . . .
C16 C 0.3246(4) 0.4763(2) 0.4136(4) 0.0602(12) Uani 1 1 d . . . . .
H16 H 0.314927 0.518608 0.408059 0.072 Uiso 1 1 calc R U . . .
C5 C 1.0070(5) 0.2529(2) 0.5407(4) 0.0687(14) Uani 1 1 d . . . . .
H5 H 1.024369 0.213224 0.519985 0.082 Uiso 1 1 calc R U . . .
C2 C 0.9525(5) 0.3705(2) 0.6045(4) 0.0686(14) Uani 1 1 d . . . . .
H2 H 0.935051 0.409700 0.627628 0.082 Uiso 1 1 calc R U . . .
C13 C 0.3505(4) 0.3498(2) 0.4337(4) 0.0647(13) Uani 1 1 d . . . . .
H13 H 0.357800 0.307377 0.440722 0.078 Uiso 1 1 calc R U . . .
C3 C 1.0413(6) 0.3322(3) 0.6787(5) 0.0876(19) Uani 1 1 d . . . . .
H3 H 1.081581 0.345896 0.751855 0.105 Uiso 1 1 calc R U . . .
C15 C 0.2391(5) 0.4421(3) 0.4589(4) 0.0688(14) Uani 1 1 d . . . . .
C20 C 0.8241(4) 0.4876(2) 0.2335(4) 0.0638(13) Uani 1 1 d . . . . .
H20A H 0.869428 0.512167 0.186672 0.077 Uiso 1 1 calc R U . . .
H20B H 0.874605 0.491127 0.312174 0.077 Uiso 1 1 calc R U . . .
C14 C 0.2503(5) 0.3795(3) 0.4706(4) 0.0710(14) Uani 1 1 d . . . . .
H14 H 0.190334 0.357723 0.503345 0.085 Uiso 1 1 calc R U . . .
C21 C 0.9570(4) 0.3949(2) 0.2169(4) 0.0648(13) Uani 1 1 d . . . . .
H21A H 0.947117 0.352457 0.192365 0.078 Uiso 1 1 calc R U . . .
H21B H 0.998249 0.395129 0.298063 0.078 Uiso 1 1 calc R U . . .
C19 C 0.6784(4) 0.5101(2) 0.2209(4) 0.0667(14) Uani 1 1 d . . . . .
H19A H 0.678404 0.549961 0.256512 0.080 Uiso 1 1 calc R U . . .
H19B H 0.632740 0.513807 0.140958 0.080 Uiso 1 1 calc R U . . .
C9 C 0.5600(4) 0.2782(2) 0.1259(4) 0.0689(14) Uani 1 1 d . . . . .
H9A H 0.521976 0.261290 0.050923 0.083 Uiso 1 1 calc R U . . .
H9B H 0.505071 0.264488 0.176840 0.083 Uiso 1 1 calc R U . . .
C4 C 1.0707(5) 0.2744(3) 0.6460(5) 0.0805(16) Uani 1 1 d . . . . .
C10 C 0.4198(4) 0.3735(3) 0.0871(4) 0.0738(14) Uani 1 1 d . . . . .
H10A H 0.372098 0.363615 0.145538 0.089 Uiso 1 1 calc R U . . .
H10B H 0.428540 0.417774 0.085423 0.089 Uiso 1 1 calc R U . . .
C22 C 1.0527(5) 0.4272(3) 0.1550(5) 0.0882(18) Uani 1 1 d . . . . .
H22A H 1.013430 0.426791 0.074425 0.132 Uiso 1 1 calc R U . . .
H22B H 1.138620 0.406302 0.170632 0.132 Uiso 1 1 calc R U . . .
H22C H 1.066239 0.468836 0.180952 0.132 Uiso 1 1 calc R U . . .
O5 O 0.6124(9) 0.3799(3) -0.2145(6) 0.215(4) Uani 1 1 d . . . . .
C11 C 0.3350(5) 0.3529(3) -0.0253(5) 0.0911(18) Uani 1 1 d . . . . .
H11A H 0.388181 0.354339 -0.081307 0.137 Uiso 1 1 calc R U . . .
H11B H 0.257594 0.379379 -0.048193 0.137 Uiso 1 1 calc R U . . .
H11C H 0.304675 0.311643 -0.018750 0.137 Uiso 1 1 calc R U . . .
O6 O 0.8254(9) 0.4136(3) -0.1687(7) 0.227(4) Uani 1 1 d . . . . .
H24 H 0.785(4) 0.4212(17) 0.127(3) 0.040(12) Uiso 1 1 d . . . . .
H23 H 0.606(4) 0.3553(17) 0.073(3) 0.042(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 1.893(3) . ?
Fe1 O2 1.901(3) . ?
Fe1 N1 2.057(3) . ?
Fe1 N3 2.056(3) . ?
Fe1 N2 2.173(4) . ?
Fe1 N4 2.184(3) . ?
Cl1 O6 1.362(6) . ?
Cl1 O3 1.396(4) . ?
Cl1 O5 1.400(6) . ?
Cl1 O4 1.402(4) . ?
O2 C12 1.317(5) . ?
F1 C4 1.479(6) . ?
F2 C15 1.389(5) . ?
O1 C1 1.319(5) . ?
N1 C7 1.289(5) . ?
N1 C8 1.477(5) . ?
N3 C18 1.287(5) . ?
N3 C19 1.475(5) . ?
N4 C20 1.468(6) . ?
N4 C21 1.495(5) . ?
N4 H24 0.84(4) . ?
N2 C9 1.485(6) . ?
N2 C10 1.496(6) . ?
N2 H23 0.84(4) . ?
C7 C6 1.445(6) . ?
C7 H7 0.9300 . ?
C12 C17 1.405(6) . ?
C12 C13 1.424(6) . ?
C18 C17 1.445(6) . ?
C18 H18 0.9300 . ?
C17 C16 1.407(6) . ?
C6 C1 1.405(6) . ?
C6 C5 1.413(6) . ?
C8 C9 1.506(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C1 C2 1.405(6) . ?
C16 C15 1.352(6) . ?
C16 H16 0.9300 . ?
C5 C4 1.366(7) . ?
C5 H5 0.9300 . ?
C2 C3 1.388(8) . ?
C2 H2 0.9300 . ?
C13 C14 1.366(6) . ?
C13 H13 0.9300 . ?
C3 C4 1.375(8) . ?
C3 H3 0.9300 . ?
C15 C14 1.375(7) . ?
C20 C19 1.528(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C14 H14 0.9300 . ?
C21 C22 1.531(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.494(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
O1 Fe1 O2 95.24(13) . . ?
O1 Fe1 N1 88.74(14) . . ?
O2 Fe1 N1 95.67(13) . . ?
O1 Fe1 N3 94.12(14) . . ?
O2 Fe1 N3 89.18(13) . . ?
N1 Fe1 N3 174.13(13) . . ?
O1 Fe1 N2 168.29(14) . . ?
O2 Fe1 N2 87.48(15) . . ?
N1 Fe1 N2 79.64(14) . . ?
N3 Fe1 N2 97.31(14) . . ?
O1 Fe1 N4 89.97(14) . . ?
O2 Fe1 N4 167.49(13) . . ?
N1 Fe1 N4 95.81(13) . . ?
N3 Fe1 N4 79.09(13) . . ?
N2 Fe1 N4 89.71(16) . . ?
O6 Cl1 O3 107.4(4) . . ?
O6 Cl1 O5 107.0(5) . . ?
O3 Cl1 O5 109.5(4) . . ?
O6 Cl1 O4 112.9(4) . . ?
O3 Cl1 O4 108.7(3) . . ?
O5 Cl1 O4 111.3(4) . . ?
C12 O2 Fe1 131.3(3) . . ?
C1 O1 Fe1 132.3(3) . . ?
C7 N1 C8 118.1(4) . . ?
C7 N1 Fe1 126.7(3) . . ?
C8 N1 Fe1 115.2(3) . . ?
C18 N3 C19 117.5(4) . . ?
C18 N3 Fe1 126.5(3) . . ?
C19 N3 Fe1 115.9(3) . . ?
C20 N4 C21 112.5(3) . . ?
C20 N4 Fe1 106.4(2) . . ?
C21 N4 Fe1 114.2(3) . . ?
C20 N4 H24 109(3) . . ?
C21 N4 H24 106(3) . . ?
Fe1 N4 H24 108(3) . . ?
C9 N2 C10 113.9(4) . . ?
C9 N2 Fe1 105.5(3) . . ?
C10 N2 Fe1 114.7(3) . . ?
C9 N2 H23 106(3) . . ?
C10 N2 H23 111(3) . . ?
Fe1 N2 H23 105(3) . . ?
N1 C7 C6 124.9(4) . . ?
N1 C7 H7 117.6 . . ?
C6 C7 H7 117.6 . . ?
O2 C12 C17 124.5(4) . . ?
O2 C12 C13 118.1(4) . . ?
C17 C12 C13 117.4(4) . . ?
N3 C18 C17 125.1(4) . . ?
N3 C18 H18 117.5 . . ?
C17 C18 H18 117.5 . . ?
C16 C17 C12 120.6(4) . . ?
C16 C17 C18 116.6(4) . . ?
C12 C17 C18 122.7(4) . . ?
C1 C6 C5 119.3(4) . . ?
C1 C6 C7 123.4(4) . . ?
C5 C6 C7 117.3(5) . . ?
N1 C8 C9 106.6(4) . . ?
N1 C8 H8A 110.4 . . ?
C9 C8 H8A 110.4 . . ?
N1 C8 H8B 110.4 . . ?
C9 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
O1 C1 C2 118.4(5) . . ?
O1 C1 C6 122.9(4) . . ?
C2 C1 C6 118.7(5) . . ?
C15 C16 C17 118.7(5) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C4 C5 C6 120.9(5) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C3 C2 C1 120.1(5) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C14 C13 C12 121.1(5) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C4 C3 C2 121.1(5) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C16 C15 C14 123.0(5) . . ?
C16 C15 F2 119.3(5) . . ?
C14 C15 F2 117.7(4) . . ?
N4 C20 C19 108.2(4) . . ?
N4 C20 H20A 110.1 . . ?
C19 C20 H20A 110.1 . . ?
N4 C20 H20B 110.1 . . ?
C19 C20 H20B 110.1 . . ?
H20A C20 H20B 108.4 . . ?
C13 C14 C15 119.2(4) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
N4 C21 C22 114.0(4) . . ?
N4 C21 H21A 108.7 . . ?
C22 C21 H21A 108.7 . . ?
N4 C21 H21B 108.7 . . ?
C22 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
N3 C19 C20 107.4(3) . . ?
N3 C19 H19A 110.2 . . ?
C20 C19 H19A 110.2 . . ?
N3 C19 H19B 110.2 . . ?
C20 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
N2 C9 C8 108.9(4) . . ?
N2 C9 H9A 109.9 . . ?
C8 C9 H9A 109.9 . . ?
N2 C9 H9B 109.9 . . ?
C8 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C5 C4 C3 119.8(6) . . ?
C5 C4 F1 121.9(6) . . ?
C3 C4 F1 118.3(5) . . ?
C11 C10 N2 115.1(4) . . ?
C11 C10 H10A 108.5 . . ?
N2 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
N2 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Fe1 O1 C1 83.7(3) . . . . ?
N1 Fe1 O1 C1 -11.9(3) . . . . ?
N3 Fe1 O1 C1 173.3(3) . . . . ?
N2 Fe1 O1 C1 -19.3(9) . . . . ?
N4 Fe1 O1 C1 -107.7(3) . . . . ?
C8 N1 C7 C6 179.5(4) . . . . ?
Fe1 N1 C7 C6 -2.3(5) . . . . ?
Fe1 O2 C12 C17 4.3(6) . . . . ?
Fe1 O2 C12 C13 -177.5(3) . . . . ?
C19 N3 C18 C17 176.4(4) . . . . ?
Fe1 N3 C18 C17 -8.0(6) . . . . ?
O2 C12 C17 C16 178.5(4) . . . . ?
C13 C12 C17 C16 0.3(6) . . . . ?
O2 C12 C17 C18 1.0(7) . . . . ?
C13 C12 C17 C18 -177.3(4) . . . . ?
N3 C18 C17 C16 -176.2(4) . . . . ?
N3 C18 C17 C12 1.4(7) . . . . ?
N1 C7 C6 C1 -0.9(6) . . . . ?
N1 C7 C6 C5 177.5(4) . . . . ?
C7 N1 C8 C9 148.0(4) . . . . ?
Fe1 N1 C8 C9 -30.3(4) . . . . ?
Fe1 O1 C1 C2 -167.8(3) . . . . ?
Fe1 O1 C1 C6 12.3(6) . . . . ?
C5 C6 C1 O1 178.0(4) . . . . ?
C7 C6 C1 O1 -3.6(6) . . . . ?
C5 C6 C1 C2 -1.8(6) . . . . ?
C7 C6 C1 C2 176.6(4) . . . . ?
C12 C17 C16 C15 -0.6(7) . . . . ?
C18 C17 C16 C15 177.1(4) . . . . ?
C1 C6 C5 C4 -0.1(6) . . . . ?
C7 C6 C5 C4 -178.6(4) . . . . ?
O1 C1 C2 C3 -178.5(4) . . . . ?
C6 C1 C2 C3 1.4(6) . . . . ?
O2 C12 C13 C14 -178.7(4) . . . . ?
C17 C12 C13 C14 -0.3(7) . . . . ?
C1 C2 C3 C4 1.1(7) . . . . ?
C17 C16 C15 C14 1.0(8) . . . . ?
C17 C16 C15 F2 -177.2(4) . . . . ?
C21 N4 C20 C19 -174.3(4) . . . . ?
Fe1 N4 C20 C19 -48.6(4) . . . . ?
C12 C13 C14 C15 0.7(7) . . . . ?
C16 C15 C14 C13 -1.0(8) . . . . ?
F2 C15 C14 C13 177.2(4) . . . . ?
C20 N4 C21 C22 -59.2(6) . . . . ?
Fe1 N4 C21 C22 179.4(4) . . . . ?
C18 N3 C19 C20 149.3(4) . . . . ?
Fe1 N3 C19 C20 -26.8(5) . . . . ?
N4 C20 C19 N3 49.9(5) . . . . ?
C10 N2 C9 C8 -175.5(4) . . . . ?
Fe1 N2 C9 C8 -48.8(4) . . . . ?
N1 C8 C9 N2 52.4(5) . . . . ?
C6 C5 C4 C3 2.6(7) . . . . ?
C6 C5 C4 F1 -179.2(4) . . . . ?
C2 C3 C4 C5 -3.1(8) . . . . ?
C2 C3 C4 F1 178.6(4) . . . . ?
C9 N2 C10 C11 -58.3(6) . . . . ?
Fe1 N2 C10 C11 -180.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C18 H18 O5 0.93 2.53 3.357(7) 149.0 3_665 yes
C8 H8A O5 0.97 2.66 3.516(8) 146.6 4_566 yes
C20 H20B F2 0.97 2.52 3.359(6) 145.0 3_666 yes
C10 H10A O2 0.97 2.63 3.137(6) 112.8 . yes
C18 H18 O5 0.93 2.53 3.357(7) 149.0 3_665 yes
C8 H8A O5 0.97 2.66 3.516(8) 146.6 4_566 yes
C20 H20B F2 0.97 2.52 3.359(6) 145.0 3_666 yes
C10 H10A O2 0.97 2.63 3.137(6) 112.8 . yes

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_300K
_database_code_depnum_ccdc_archive 'CCDC 2310298'
loop_
_audit_author_name
_audit_author_address
'Clara S. B. Gomes'
;LAQV REQUIMTE, FCT, Universidade NOVA de Lisboa
Portugal
;
_audit_update_record             
;
2023-11-25 deposited with the CCDC.	2024-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H28 Cl3 Fe N4 O6'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            black
_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         606.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration ?

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

_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.
;

_cell_length_a                   9.9911(10)
_cell_length_b                   23.030(2)
_cell_length_c                   12.0882(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.748(4)
_cell_angle_gamma                90
_cell_volume                     2701.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9422
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      28.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_F_000             1252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.898
_shelx_estimated_absorpt_T_min   0.715
_shelx_estimated_absorpt_T_max   0.774
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_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            136496
_diffrn_reflns_av_unetI/netI     0.1653
_diffrn_reflns_av_R_equivalents  0.2596
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.477
_diffrn_reflns_theta_max         28.290
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6714
_reflns_number_gt                4323
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0920P)²] 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         6714
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1431
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1553
_refine_ls_wR_factor_gt          0.1458
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.72027(4) 0.62621(2) 0.74867(3) 0.03382(13) Uani 1 1 d . . . . .
Cl1 Cl 0.17029(10) 0.51663(4) 0.99833(8) 0.0647(3) Uani 1 1 d . . . . .
Cl3 Cl 0.75081(13) 0.60594(5) 0.33857(7) 0.0749(3) Uani 1 1 d . . . . .
Cl2 Cl 1.22737(12) 0.76657(5) 1.21052(8) 0.0762(3) Uani 1 1 d . . . . .
O2 O 0.8498(2) 0.61627(9) 0.89104(15) 0.0433(5) Uani 1 1 d . . . . .
O1 O 0.5699(2) 0.64742(9) 0.81308(17) 0.0450(5) Uani 1 1 d . . . . .
N3 N 0.8058(2) 0.70911(10) 0.74162(17) 0.0350(5) Uani 1 1 d . . . . .
N4 N 0.5991(3) 0.65825(12) 0.5828(2) 0.0433(6) Uani 1 1 d . . . . .
N2 N 0.8632(2) 0.58110(11) 0.6613(2) 0.0404(5) Uani 1 1 d . . . . .
C18 C 0.8960(3) 0.73382(13) 0.8198(2) 0.0361(6) Uani 1 1 d . . . . .
H18 H 0.923026 0.771136 0.805175 0.043 Uiso 1 1 calc R U . . .
N1 N 0.6410(3) 0.54167(11) 0.73270(19) 0.0407(5) Uani 1 1 d . . . . .
C12 C 0.9288(3) 0.65250(12) 0.9617(2) 0.0356(6) Uani 1 1 d . . . . .
C17 C 0.9601(3) 0.70869(12) 0.9294(2) 0.0349(6) Uani 1 1 d . . . . .
C5 C 0.3723(3) 0.52564(14) 0.8870(2) 0.0427(7) Uani 1 1 d . . . . .
H5 H 0.363099 0.485645 0.877477 0.051 Uiso 1 1 calc R U . . .
C2 C 0.4004(3) 0.64440(14) 0.9181(2) 0.0436(7) Uani 1 1 d . . . . .
H2 H 0.408422 0.684337 0.929133 0.052 Uiso 1 1 calc R U . . .
C1 C 0.4843(3) 0.61624(12) 0.8563(2) 0.0362(6) Uani 1 1 d . . . . .
C3 C 0.3066(3) 0.61404(15) 0.9627(2) 0.0474(7) Uani 1 1 d . . . . .
H3 H 0.253202 0.633338 1.004452 0.057 Uiso 1 1 calc R U . . .
C16 C 1.0533(3) 0.74368(14) 1.0076(2) 0.0430(6) Uani 1 1 d . . . . .
H16 H 1.075331 0.780595 0.986199 0.052 Uiso 1 1 calc R U . . .
C14 C 1.0746(3) 0.66941(14) 1.1499(2) 0.0468(7) Uani 1 1 d . . . . .
H14 H 1.110726 0.657011 1.224269 0.056 Uiso 1 1 calc R U . . .
O5 O 0.7017(4) 0.56206(15) 0.4004(2) 0.1067(13) Uani 1 1 d . . . . .
C15 C 1.1114(3) 0.72357(15) 1.1147(2) 0.0476(7) Uani 1 1 d . . . . .
C6 C 0.4689(3) 0.55582(12) 0.8413(2) 0.0368(6) Uani 1 1 d . . . . .
C13 C 0.9850(3) 0.63437(13) 1.0749(2) 0.0418(7) Uani 1 1 d . . . . .
H13 H 0.961031 0.598297 1.098884 0.050 Uiso 1 1 calc R U . . .
C4 C 0.2920(3) 0.55484(14) 0.9453(2) 0.0429(7) Uani 1 1 d . . . . .
C7 C 0.5493(3) 0.52189(13) 0.7797(2) 0.0414(6) Uani 1 1 d . . . . .
H7 H 0.532405 0.482158 0.773927 0.050 Uiso 1 1 calc R U . . .
C9 C 0.8604(4) 0.51898(15) 0.6933(3) 0.0533(8) Uani 1 1 d . . . . .
H9A H 0.907355 0.513793 0.772661 0.064 Uiso 1 1 calc R U . . .
H9B H 0.907229 0.495713 0.647147 0.064 Uiso 1 1 calc R U . . .
C19 C 0.7494(3) 0.74146(15) 0.6363(2) 0.0495(8) Uani 1 1 d . . . . .
H19A H 0.802998 0.733569 0.580805 0.059 Uiso 1 1 calc R U . . .
H19B H 0.752880 0.782837 0.651713 0.059 Uiso 1 1 calc R U . . .
C21 C 0.4576(4) 0.63385(18) 0.5504(3) 0.0597(9) Uani 1 1 d . . . . .
H21A H 0.411029 0.642759 0.610178 0.072 Uiso 1 1 calc R U . . .
H21B H 0.464118 0.591929 0.545965 0.072 Uiso 1 1 calc R U . . .
C20 C 0.6024(4) 0.72237(15) 0.5909(3) 0.0534(8) Uani 1 1 d . . . . .
H20A H 0.546213 0.735304 0.641486 0.064 Uiso 1 1 calc R U . . .
H20B H 0.565799 0.739290 0.516392 0.064 Uiso 1 1 calc R U . . .
C10 C 1.0053(3) 0.60554(17) 0.6853(3) 0.0551(8) Uani 1 1 d . . . . .
H10A H 1.046043 0.602359 0.766347 0.066 Uiso 1 1 calc R U . . .
H10B H 0.999377 0.646508 0.666122 0.066 Uiso 1 1 calc R U . . .
C8 C 0.7134(4) 0.50014(16) 0.6743(3) 0.0603(9) Uani 1 1 d . . . . .
H8A H 0.670341 0.499424 0.593480 0.072 Uiso 1 1 calc R U . . .
H8B H 0.708670 0.461388 0.704660 0.072 Uiso 1 1 calc R U . . .
O6 O 0.6545(7) 0.6169(2) 0.2388(4) 0.168(2) Uani 1 1 d . . . . .
C11 C 1.0998(4) 0.5763(2) 0.6213(4) 0.0779(12) Uani 1 1 d . . . . .
H11A H 1.188861 0.594416 0.641160 0.117 Uiso 1 1 calc R U . . .
H11B H 1.108561 0.535939 0.641220 0.117 Uiso 1 1 calc R U . . .
H11C H 1.061828 0.580152 0.540851 0.117 Uiso 1 1 calc R U . . .
O4 O 0.8692(6) 0.5866(3) 0.3063(5) 0.176(2) Uani 1 1 d . . . . .
C22 C 0.3704(5) 0.6561(2) 0.4381(3) 0.0828(13) Uani 1 1 d . . . . .
H22A H 0.280917 0.638404 0.423427 0.124 Uiso 1 1 calc R U . . .
H22B H 0.360889 0.697526 0.442146 0.124 Uiso 1 1 calc R U . . .
H22C H 0.414061 0.646616 0.377832 0.124 Uiso 1 1 calc R U . . .
O3 O 0.7818(6) 0.65387(17) 0.4089(3) 0.1439(19) Uani 1 1 d . . . . .
H24 H 0.644(4) 0.6518(16) 0.527(3) 0.059(10) Uiso 1 1 d . . . . .
H23 H 0.824(3) 0.5816(14) 0.588(3) 0.042(8) 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 1.905(2) . ?
Fe1 O1 1.913(2) . ?
Fe1 N1 2.094(2) . ?
Fe1 N3 2.102(2) . ?
Fe1 N4 2.209(2) . ?
Fe1 N2 2.225(2) . ?
Cl1 C4 1.742(3) . ?
Cl3 O6 1.375(4) . ?
Cl3 O3 1.383(3) . ?
Cl3 O4 1.403(5) . ?
Cl3 O5 1.413(3) . ?
Cl2 C15 1.740(3) . ?
O2 C12 1.315(3) . ?
O1 C1 1.316(3) . ?
N3 C18 1.274(3) . ?
N3 C19 1.467(3) . ?
N4 C20 1.480(4) . ?
N4 C21 1.485(4) . ?
N4 H24 0.91(3) . ?
N2 C9 1.484(4) . ?
N2 C10 1.490(4) . ?
N2 H23 0.88(3) . ?
C18 C17 1.449(4) . ?
C18 H18 0.9300 . ?
N1 C7 1.272(4) . ?
N1 C8 1.475(4) . ?
C12 C17 1.408(4) . ?
C12 C13 1.413(4) . ?
C17 C16 1.411(4) . ?
C5 C4 1.364(4) . ?
C5 C6 1.405(4) . ?
C5 H5 0.9300 . ?
C2 C3 1.377(4) . ?
C2 C1 1.407(4) . ?
C2 H2 0.9300 . ?
C1 C6 1.407(4) . ?
C3 C4 1.382(5) . ?
C3 H3 0.9300 . ?
C16 C15 1.367(4) . ?
C16 H16 0.9300 . ?
C14 C13 1.375(4) . ?
C14 C15 1.396(5) . ?
C14 H14 0.9300 . ?
C6 C7 1.447(4) . ?
C13 H13 0.9300 . ?
C7 H7 0.9300 . ?
C9 C8 1.497(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C19 C20 1.506(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C21 C22 1.518(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C10 C11 1.513(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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 O1 95.37(9) . . ?
O2 Fe1 N1 97.60(9) . . ?
O1 Fe1 N1 87.62(9) . . ?
O2 Fe1 N3 87.15(8) . . ?
O1 Fe1 N3 98.69(9) . . ?
N1 Fe1 N3 171.75(8) . . ?
O2 Fe1 N4 165.55(9) . . ?
O1 Fe1 N4 88.30(9) . . ?
N1 Fe1 N4 96.51(10) . . ?
N3 Fe1 N4 78.48(9) . . ?
O2 Fe1 N2 89.87(9) . . ?
O1 Fe1 N2 165.30(9) . . ?
N1 Fe1 N2 78.07(9) . . ?
N3 Fe1 N2 95.27(9) . . ?
N4 Fe1 N2 90.01(9) . . ?
O6 Cl3 O3 113.6(3) . . ?
O6 Cl3 O4 106.0(4) . . ?
O3 Cl3 O4 110.1(4) . . ?
O6 Cl3 O5 109.6(3) . . ?
O3 Cl3 O5 107.5(2) . . ?
O4 Cl3 O5 110.0(3) . . ?
C12 O2 Fe1 133.20(18) . . ?
C1 O1 Fe1 132.05(19) . . ?
C18 N3 C19 118.3(2) . . ?
C18 N3 Fe1 126.76(18) . . ?
C19 N3 Fe1 114.86(18) . . ?
C20 N4 C21 113.6(3) . . ?
C20 N4 Fe1 105.90(18) . . ?
C21 N4 Fe1 113.3(2) . . ?
C20 N4 H24 102(2) . . ?
C21 N4 H24 111(2) . . ?
Fe1 N4 H24 111(2) . . ?
C9 N2 C10 112.9(3) . . ?
C9 N2 Fe1 105.85(16) . . ?
C10 N2 Fe1 114.87(19) . . ?
C9 N2 H23 104(2) . . ?
C10 N2 H23 111(2) . . ?
Fe1 N2 H23 107(2) . . ?
N3 C18 C17 125.5(3) . . ?
N3 C18 H18 117.3 . . ?
C17 C18 H18 117.3 . . ?
C7 N1 C8 117.9(3) . . ?
C7 N1 Fe1 126.08(19) . . ?
C8 N1 Fe1 115.44(19) . . ?
O2 C12 C17 122.8(2) . . ?
O2 C12 C13 118.7(3) . . ?
C17 C12 C13 118.5(3) . . ?
C12 C17 C16 119.6(2) . . ?
C12 C17 C18 122.8(2) . . ?
C16 C17 C18 117.5(3) . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
O1 C1 C2 119.0(3) . . ?
O1 C1 C6 123.3(2) . . ?
C2 C1 C6 117.6(3) . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C15 C16 C17 120.3(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 Cl2 120.2(3) . . ?
C14 C15 Cl2 119.2(2) . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 C7 116.9(3) . . ?
C1 C6 C7 122.9(2) . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 Cl1 119.3(2) . . ?
C3 C4 Cl1 120.0(2) . . ?
N1 C7 C6 125.7(3) . . ?
N1 C7 H7 117.2 . . ?
C6 C7 H7 117.2 . . ?
N2 C9 C8 108.5(3) . . ?
N2 C9 H9A 110.0 . . ?
C8 C9 H9A 110.0 . . ?
N2 C9 H9B 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
N3 C19 C20 108.0(2) . . ?
N3 C19 H19A 110.1 . . ?
C20 C19 H19A 110.1 . . ?
N3 C19 H19B 110.1 . . ?
C20 C19 H19B 110.1 . . ?
H19A C19 H19B 108.4 . . ?
N4 C21 C22 114.6(3) . . ?
N4 C21 H21A 108.6 . . ?
C22 C21 H21A 108.6 . . ?
N4 C21 H21B 108.6 . . ?
C22 C21 H21B 108.6 . . ?
H21A C21 H21B 107.6 . . ?
N4 C20 C19 108.7(3) . . ?
N4 C20 H20A 110.0 . . ?
C19 C20 H20A 110.0 . . ?
N4 C20 H20B 110.0 . . ?
C19 C20 H20B 110.0 . . ?
H20A C20 H20B 108.3 . . ?
N2 C10 C11 114.5(3) . . ?
N2 C10 H10A 108.6 . . ?
C11 C10 H10A 108.6 . . ?
N2 C10 H10B 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
N1 C8 C9 108.3(3) . . ?
N1 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
N1 C8 H8B 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C19 N3 C18 C17 178.7(3) . . . . ?
Fe1 N3 C18 C17 1.4(4) . . . . ?
Fe1 O2 C12 C17 -17.6(4) . . . . ?
Fe1 O2 C12 C13 162.4(2) . . . . ?
O2 C12 C17 C16 -175.6(3) . . . . ?
C13 C12 C17 C16 4.3(4) . . . . ?
O2 C12 C17 C18 7.0(4) . . . . ?
C13 C12 C17 C18 -173.0(2) . . . . ?
N3 C18 C17 C12 0.4(4) . . . . ?
N3 C18 C17 C16 -177.0(3) . . . . ?
Fe1 O1 C1 C2 167.5(2) . . . . ?
Fe1 O1 C1 C6 -14.4(4) . . . . ?
C3 C2 C1 O1 178.4(3) . . . . ?
C3 C2 C1 C6 0.1(4) . . . . ?
C1 C2 C3 C4 -1.1(5) . . . . ?
C12 C17 C16 C15 -1.0(4) . . . . ?
C18 C17 C16 C15 176.5(3) . . . . ?
C17 C16 C15 C14 -3.0(4) . . . . ?
C17 C16 C15 Cl2 179.5(2) . . . . ?
C13 C14 C15 C16 3.6(5) . . . . ?
C13 C14 C15 Cl2 -178.9(2) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C4 C5 C6 C7 -179.4(3) . . . . ?
O1 C1 C6 C5 -178.0(3) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
O1 C1 C6 C7 2.0(4) . . . . ?
C2 C1 C6 C7 -179.8(3) . . . . ?
C15 C14 C13 C12 -0.1(5) . . . . ?
O2 C12 C13 C14 176.2(3) . . . . ?
C17 C12 C13 C14 -3.8(4) . . . . ?
C6 C5 C4 C3 -1.6(4) . . . . ?
C6 C5 C4 Cl1 178.5(2) . . . . ?
C2 C3 C4 C5 1.9(5) . . . . ?
C2 C3 C4 Cl1 -178.3(2) . . . . ?
C8 N1 C7 C6 179.5(3) . . . . ?
Fe1 N1 C7 C6 8.6(4) . . . . ?
C5 C6 C7 N1 -180.0(3) . . . . ?
C1 C6 C7 N1 -0.1(5) . . . . ?
C10 N2 C9 C8 175.6(3) . . . . ?
Fe1 N2 C9 C8 49.2(3) . . . . ?
C18 N3 C19 C20 -148.1(3) . . . . ?
Fe1 N3 C19 C20 29.6(3) . . . . ?
C20 N4 C21 C22 57.7(4) . . . . ?
Fe1 N4 C21 C22 178.5(3) . . . . ?
C21 N4 C20 C19 173.9(2) . . . . ?
Fe1 N4 C20 C19 49.0(3) . . . . ?
N3 C19 C20 N4 -52.4(3) . . . . ?
C9 N2 C10 C11 61.2(4) . . . . ?
Fe1 N2 C10 C11 -177.3(3) . . . . ?
C7 N1 C8 C9 -143.5(3) . . . . ?
Fe1 N1 C8 C9 28.4(4) . . . . ?
N2 C9 C8 N1 -51.6(4) . . . . ?

_refine_diff_density_max         0.843
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.190

####################################################################### 
# 
# 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_110K
_database_code_depnum_ccdc_archive 'CCDC 2310299'
loop_
_audit_author_name
_audit_author_address
'Clara S. B. Gomes'
;LAQV REQUIMTE, FCT, Universidade NOVA de Lisboa
Portugal
;
_audit_update_record             
;
2023-11-25 deposited with the CCDC.	2024-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C22 H28 Cl2 Fe N4 O2, Cl O4'
_chemical_formula_sum            'C22 H28 Cl3 Fe N4 O6'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_diffrn_ambient_temperature      110(2)
_chemical_formula_weight         606.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration ?

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

_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.
;

_cell_length_a                   9.8405(5)
_cell_length_b                   22.8166(9)
_cell_length_c                   11.9228(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.146(2)
_cell_angle_gamma                90
_cell_volume                     2595.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    53569
_cell_measurement_theta_min      3.002
_cell_measurement_theta_max      25.701
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_F_000             1252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.935
_shelx_estimated_absorpt_T_min   0.850
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53569
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.1102
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.002
_diffrn_reflns_theta_max         25.701
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4923
_reflns_number_gt                3749
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    Mercury
_computing_publication_material  'WinGX and enCIFer'
_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)+(0.0305P)²+1.6328P] 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         4923
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0746
_refine_ls_wR_factor_gt          0.0687
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 0.69926(3) 0.37436(2) 0.74090(3) 0.01156(9) Uani 1 1 d . . . . .
Cl2 Cl 0.15897(6) 0.46955(3) 1.01208(6) 0.02367(16) Uani 1 1 d . . . . .
Cl3 Cl 0.74413(7) 0.40578(3) 0.34288(6) 0.02492(16) Uani 1 1 d . . . . .
Cl1 Cl 1.19583(7) 0.24237(3) 1.22056(6) 0.03153(18) Uani 1 1 d . . . . .
O2 O 0.55720(16) 0.34421(6) 0.80464(14) 0.0142(4) Uani 1 1 d . . . . .
O1 O 0.81262(16) 0.39094(6) 0.88699(14) 0.0145(4) Uani 1 1 d . . . . .
N3 N 0.63254(19) 0.45429(8) 0.73990(17) 0.0127(4) Uani 1 1 d . . . . .
N1 N 0.77004(19) 0.29560(8) 0.73929(16) 0.0124(4) Uani 1 1 d . . . . .
N4 N 0.8463(2) 0.41152(8) 0.66684(19) 0.0140(4) Uani 1 1 d . . . . .
N2 N 0.5777(2) 0.35241(9) 0.58186(19) 0.0155(5) Uani 1 1 d . . . . .
O3 O 0.7802(2) 0.35484(8) 0.41574(17) 0.0375(5) Uani 1 1 d . . . . .
O4 O 0.6805(2) 0.44741(9) 0.40581(17) 0.0408(5) Uani 1 1 d . . . . .
O6 O 0.6482(2) 0.39073(9) 0.23727(18) 0.0463(6) Uani 1 1 d . . . . .
O5 O 0.8680(2) 0.43024(10) 0.3205(2) 0.0517(6) Uani 1 1 d . . . . .
C12 C 0.4759(2) 0.37511(10) 0.8556(2) 0.0125(5) Uani 1 1 d . . . . .
C13 C 0.3896(2) 0.34434(10) 0.9144(2) 0.0147(5) Uani 1 1 d . . . . .
H13 H 0.397101 0.302880 0.920094 0.018 Uiso 1 1 calc R U . . .
C1 C 0.8862(2) 0.35303(10) 0.9610(2) 0.0132(5) Uani 1 1 d . . . . .
C17 C 0.4635(2) 0.43698(10) 0.8514(2) 0.0129(5) Uani 1 1 d . . . . .
C18 C 0.5427(2) 0.47326(10) 0.7924(2) 0.0141(5) Uani 1 1 d . . . . .
H18 H 0.527336 0.514360 0.792399 0.017 Uiso 1 1 calc R U . . .
C14 C 0.2952(2) 0.37247(11) 0.9633(2) 0.0169(5) Uani 1 1 d . . . . .
H14 H 0.238307 0.350665 1.002154 0.020 Uiso 1 1 calc R U . . .
C6 C 0.9190(2) 0.29542(10) 0.9319(2) 0.0134(5) Uani 1 1 d . . . . .
C16 C 0.3659(2) 0.46500(10) 0.9014(2) 0.0149(5) Uani 1 1 d . . . . .
H16 H 0.357299 0.506464 0.897410 0.018 Uiso 1 1 calc R U . . .
C15 C 0.2833(2) 0.43348(10) 0.9556(2) 0.0147(5) Uani 1 1 d . . . . .
C7 C 0.8581(2) 0.26958(10) 0.8214(2) 0.0142(5) Uani 1 1 d . . . . .
H7 H 0.884579 0.230643 0.808174 0.017 Uiso 1 1 calc R U . . .
C20 C 0.8537(2) 0.47469(10) 0.6984(2) 0.0186(6) Uani 1 1 d . . . . .
H20A H 0.901927 0.497005 0.648226 0.022 Uiso 1 1 calc R U . . .
H20B H 0.906205 0.479945 0.779865 0.022 Uiso 1 1 calc R U . . .
C19 C 0.7049(3) 0.49596(10) 0.6816(2) 0.0194(6) Uani 1 1 d . . . . .
H19A H 0.703766 0.535561 0.715298 0.023 Uiso 1 1 calc R U . . .
H19B H 0.657997 0.497928 0.598171 0.023 Uiso 1 1 calc R U . . .
C9 C 0.5697(3) 0.28746(10) 0.5792(2) 0.0189(6) Uani 1 1 d . . . . .
H9A H 0.534595 0.273520 0.498694 0.023 Uiso 1 1 calc R U . . .
H9B H 0.505093 0.273569 0.625436 0.023 Uiso 1 1 calc R U . . .
C2 C 0.9383(2) 0.37161(11) 1.0765(2) 0.0169(5) Uani 1 1 d . . . . .
H2 H 0.909637 0.408408 1.100133 0.020 Uiso 1 1 calc R U . . .
C3 C 1.0293(2) 0.33752(10) 1.1550(2) 0.0186(6) Uani 1 1 d . . . . .
H3 H 1.064178 0.350964 1.232098 0.022 Uiso 1 1 calc R U . . .
C5 C 1.0145(2) 0.26155(10) 1.0136(2) 0.0181(6) Uani 1 1 d . . . . .
H5 H 1.040079 0.223559 0.993351 0.022 Uiso 1 1 calc R U . . .
C8 C 0.7155(3) 0.26439(11) 0.6294(2) 0.0191(6) Uani 1 1 d . . . . .
H8A H 0.712796 0.221655 0.643121 0.023 Uiso 1 1 calc R U . . .
H8B H 0.776001 0.271751 0.575642 0.023 Uiso 1 1 calc R U . . .
C4 C 1.0707(3) 0.28320(11) 1.1221(2) 0.0209(6) Uani 1 1 d . . . . .
C10 C 0.4363(2) 0.38029(11) 0.5512(2) 0.0226(6) Uani 1 1 d . . . . .
H10A H 0.448113 0.423189 0.545617 0.027 Uiso 1 1 calc R U . . .
H10B H 0.389622 0.372977 0.614647 0.027 Uiso 1 1 calc R U . . .
C21 C 0.9870(2) 0.38373(11) 0.6941(2) 0.0190(6) Uani 1 1 d . . . . .
H21A H 0.976650 0.342108 0.670079 0.023 Uiso 1 1 calc R U . . .
H21B H 1.025921 0.384672 0.778923 0.023 Uiso 1 1 calc R U . . .
C22 C 1.0902(3) 0.41287(12) 0.6361(3) 0.0277(7) Uani 1 1 d . . . . .
H22A H 1.050932 0.413672 0.552231 0.042 Uiso 1 1 calc R U . . .
H22B H 1.178188 0.390740 0.653516 0.042 Uiso 1 1 calc R U . . .
H22C H 1.108116 0.453043 0.664983 0.042 Uiso 1 1 calc R U . . .
C11 C 0.3411(3) 0.35855(12) 0.4385(2) 0.0276(7) Uani 1 1 d . . . . .
H11A H 0.390408 0.361354 0.376513 0.041 Uiso 1 1 calc R U . . .
H11B H 0.256163 0.382675 0.418775 0.041 Uiso 1 1 calc R U . . .
H11C H 0.315368 0.317638 0.447462 0.041 Uiso 1 1 calc R U . . .
H2B H 0.616(2) 0.3611(10) 0.530(2) 0.009(7) Uiso 1 1 d . . . . .
H4B H 0.816(3) 0.4097(11) 0.590(2) 0.021(7) 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 1.8632(16) . ?
Fe1 O2 1.8773(16) . ?
Fe1 N1 1.9291(19) . ?
Fe1 N3 1.9374(18) . ?
Fe1 N2 2.042(2) . ?
Fe1 N4 2.053(2) . ?
Cl2 C15 1.741(2) . ?
Cl3 O6 1.419(2) . ?
Cl3 O5 1.424(2) . ?
Cl3 O3 1.4423(19) . ?
Cl3 O4 1.4445(19) . ?
Cl1 C4 1.748(2) . ?
O2 C12 1.321(3) . ?
O1 C1 1.318(3) . ?
N3 C18 1.277(3) . ?
N3 C19 1.461(3) . ?
N1 C7 1.283(3) . ?
N1 C8 1.472(3) . ?
N4 C21 1.485(3) . ?
N4 C20 1.487(3) . ?
N4 H4B 0.89(3) . ?
N2 C9 1.484(3) . ?
N2 C10 1.492(3) . ?
N2 H2B 0.82(3) . ?
C12 C13 1.413(3) . ?
C12 C17 1.417(3) . ?
C13 C14 1.371(3) . ?
C13 H13 0.9500 . ?
C1 C2 1.412(3) . ?
C1 C6 1.417(3) . ?
C17 C16 1.402(3) . ?
C17 C18 1.434(3) . ?
C18 H18 0.9500 . ?
C14 C15 1.398(3) . ?
C14 H14 0.9500 . ?
C6 C5 1.408(3) . ?
C6 C7 1.434(3) . ?
C16 C15 1.361(3) . ?
C16 H16 0.9500 . ?
C7 H7 0.9500 . ?
C20 C19 1.510(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C9 C8 1.508(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C2 C3 1.369(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(4) . ?
C3 H3 0.9500 . ?
C5 C4 1.368(4) . ?
C5 H5 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 C11 1.521(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C21 C22 1.515(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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 O2 91.77(7) . . ?
O1 Fe1 N1 93.63(7) . . ?
O2 Fe1 N1 88.23(7) . . ?
O1 Fe1 N3 86.51(7) . . ?
O2 Fe1 N3 93.59(7) . . ?
N1 Fe1 N3 178.17(8) . . ?
O1 Fe1 N2 177.48(7) . . ?
O2 Fe1 N2 87.75(8) . . ?
N1 Fe1 N2 83.88(8) . . ?
N3 Fe1 N2 95.99(8) . . ?
O1 Fe1 N4 89.68(8) . . ?
O2 Fe1 N4 176.41(7) . . ?
N1 Fe1 N4 94.96(8) . . ?
N3 Fe1 N4 83.22(8) . . ?
N2 Fe1 N4 90.94(9) . . ?
O6 Cl3 O5 110.02(14) . . ?
O6 Cl3 O3 110.61(13) . . ?
O5 Cl3 O3 109.45(14) . . ?
O6 Cl3 O4 109.97(13) . . ?
O5 Cl3 O4 109.83(14) . . ?
O3 Cl3 O4 106.92(12) . . ?
C12 O2 Fe1 125.85(14) . . ?
C1 O1 Fe1 126.69(14) . . ?
C18 N3 C19 119.2(2) . . ?
C18 N3 Fe1 126.16(16) . . ?
C19 N3 Fe1 114.32(15) . . ?
C7 N1 C8 119.11(19) . . ?
C7 N1 Fe1 126.96(16) . . ?
C8 N1 Fe1 113.92(14) . . ?
C21 N4 C20 111.89(19) . . ?
C21 N4 Fe1 116.53(15) . . ?
C20 N4 Fe1 106.74(15) . . ?
C21 N4 H4B 105.4(17) . . ?
C20 N4 H4B 106.7(17) . . ?
Fe1 N4 H4B 109.2(17) . . ?
C9 N2 C10 112.30(19) . . ?
C9 N2 Fe1 106.29(15) . . ?
C10 N2 Fe1 115.00(16) . . ?
C9 N2 H2B 105.0(17) . . ?
C10 N2 H2B 106.4(17) . . ?
Fe1 N2 H2B 111.5(17) . . ?
O2 C12 C13 117.9(2) . . ?
O2 C12 C17 124.9(2) . . ?
C13 C12 C17 117.1(2) . . ?
C14 C13 C12 122.0(2) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
O1 C1 C2 117.7(2) . . ?
O1 C1 C6 124.4(2) . . ?
C2 C1 C6 117.8(2) . . ?
C16 C17 C12 120.1(2) . . ?
C16 C17 C18 117.2(2) . . ?
C12 C17 C18 122.7(2) . . ?
N3 C18 C17 124.7(2) . . ?
N3 C18 H18 117.6 . . ?
C17 C18 H18 117.6 . . ?
C13 C14 C15 119.5(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 C7 117.9(2) . . ?
C1 C6 C7 122.5(2) . . ?
C15 C16 C17 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 Cl2 119.44(18) . . ?
C14 C15 Cl2 120.06(18) . . ?
N1 C7 C6 124.3(2) . . ?
N1 C7 H7 117.9 . . ?
C6 C7 H7 117.9 . . ?
N4 C20 C19 106.97(19) . . ?
N4 C20 H20A 110.3 . . ?
C19 C20 H20A 110.3 . . ?
N4 C20 H20B 110.3 . . ?
C19 C20 H20B 110.3 . . ?
H20A C20 H20B 108.6 . . ?
N3 C19 C20 107.31(19) . . ?
N3 C19 H19A 110.3 . . ?
C20 C19 H19A 110.3 . . ?
N3 C19 H19B 110.3 . . ?
C20 C19 H19B 110.3 . . ?
H19A C19 H19B 108.5 . . ?
N2 C9 C8 107.47(19) . . ?
N2 C9 H9A 110.2 . . ?
C8 C9 H9A 110.2 . . ?
N2 C9 H9B 110.2 . . ?
C8 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C3 C2 C1 121.1(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
N1 C8 C9 106.78(19) . . ?
N1 C8 H8A 110.4 . . ?
C9 C8 H8A 110.4 . . ?
N1 C8 H8B 110.4 . . ?
C9 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 Cl1 119.9(2) . . ?
C3 C4 Cl1 119.47(19) . . ?
N2 C10 C11 114.4(2) . . ?
N2 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
N2 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
N4 C21 C22 113.9(2) . . ?
N4 C21 H21A 108.8 . . ?
C22 C21 H21A 108.8 . . ?
N4 C21 H21B 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Fe1 O2 C12 70.89(17) . . . . ?
N1 Fe1 O2 C12 164.47(18) . . . . ?
N3 Fe1 O2 C12 -15.72(18) . . . . ?
N2 Fe1 O2 C12 -111.59(18) . . . . ?
O2 Fe1 O1 C1 76.40(18) . . . . ?
N1 Fe1 O1 C1 -11.94(19) . . . . ?
N3 Fe1 O1 C1 169.89(19) . . . . ?
N4 Fe1 O1 C1 -106.89(18) . . . . ?
Fe1 O2 C12 C13 -170.33(15) . . . . ?
Fe1 O2 C12 C17 12.9(3) . . . . ?
O2 C12 C13 C14 -175.7(2) . . . . ?
C17 C12 C13 C14 1.4(3) . . . . ?
Fe1 O1 C1 C2 -165.28(16) . . . . ?
Fe1 O1 C1 C6 16.2(3) . . . . ?
O2 C12 C17 C16 175.1(2) . . . . ?
C13 C12 C17 C16 -1.7(3) . . . . ?
O2 C12 C17 C18 -1.8(4) . . . . ?
C13 C12 C17 C18 -178.6(2) . . . . ?
C19 N3 C18 C17 179.1(2) . . . . ?
Fe1 N3 C18 C17 -7.3(3) . . . . ?
C16 C17 C18 N3 -178.0(2) . . . . ?
C12 C17 C18 N3 -1.0(4) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
O1 C1 C6 C5 171.0(2) . . . . ?
C2 C1 C6 C5 -7.5(3) . . . . ?
O1 C1 C6 C7 -9.2(4) . . . . ?
C2 C1 C6 C7 172.3(2) . . . . ?
C12 C17 C16 C15 0.8(3) . . . . ?
C18 C17 C16 C15 177.8(2) . . . . ?
C17 C16 C15 C14 0.6(4) . . . . ?
C17 C16 C15 Cl2 -177.67(18) . . . . ?
C13 C14 C15 C16 -0.9(4) . . . . ?
C13 C14 C15 Cl2 177.34(18) . . . . ?
C8 N1 C7 C6 179.7(2) . . . . ?
Fe1 N1 C7 C6 0.8(3) . . . . ?
C5 C6 C7 N1 -179.8(2) . . . . ?
C1 C6 C7 N1 0.4(4) . . . . ?
C21 N4 C20 C19 -172.7(2) . . . . ?
Fe1 N4 C20 C19 -44.1(2) . . . . ?
C18 N3 C19 C20 142.9(2) . . . . ?
Fe1 N3 C19 C20 -31.4(2) . . . . ?
N4 C20 C19 N3 49.2(3) . . . . ?
C10 N2 C9 C8 -171.2(2) . . . . ?
Fe1 N2 C9 C8 -44.6(2) . . . . ?
O1 C1 C2 C3 -172.0(2) . . . . ?
C6 C1 C2 C3 6.6(3) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C1 C6 C5 C4 2.8(3) . . . . ?
C7 C6 C5 C4 -177.0(2) . . . . ?
C7 N1 C8 C9 149.8(2) . . . . ?
Fe1 N1 C8 C9 -31.1(2) . . . . ?
N2 C9 C8 N1 49.4(3) . . . . ?
C6 C5 C4 C3 3.2(4) . . . . ?
C6 C5 C4 Cl1 -176.83(18) . . . . ?
C2 C3 C4 C5 -4.2(4) . . . . ?
C2 C3 C4 Cl1 175.79(19) . . . . ?
C9 N2 C10 C11 -52.0(3) . . . . ?
Fe1 N2 C10 C11 -173.70(18) . . . . ?
C20 N4 C21 C22 -57.3(3) . . . . ?
Fe1 N4 C21 C22 179.52(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C20 H20B Cl2 0.99 2.94 3.710(3) 134.9 3_667 yes
C19 H19B O4 0.99 2.62 3.422(3) 137.7 . yes
C10 H10B O2 0.99 2.54 3.077(3) 113.8 . yes
C21 H21A Cl1 0.99 2.85 3.505(2) 124.7 4_565 yes
N2 H2B O3 0.82(3) 2.36(3) 3.135(3) 157(2) . yes
N2 H2B O4 0.82(3) 2.64(3) 3.342(3) 145(2) . yes
N4 H4B Cl3 0.89(3) 2.86(3) 3.748(2) 175(2) . yes
N4 H4B O3 0.89(3) 2.38(3) 3.179(3) 150(2) . yes
N4 H4B O4 0.89(3) 2.43(3) 3.246(3) 152(2) . yes
C20 H20B Cl2 0.99 2.94 3.710(3) 134.9 3_667 yes
C19 H19B O4 0.99 2.62 3.422(3) 137.7 . yes
C10 H10B O2 0.99 2.54 3.077(3) 113.8 . yes
C21 H21A Cl1 0.99 2.85 3.505(2) 124.7 4_565 yes
N2 H2B O3 0.82(3) 2.36(3) 3.135(3) 157(2) . yes
N2 H2B O4 0.82(3) 2.64(3) 3.342(3) 145(2) . yes
N4 H4B Cl3 0.89(3) 2.86(3) 3.748(2) 175(2) . yes
N4 H4B O3 0.89(3) 2.38(3) 3.179(3) 150(2) . yes
N4 H4B O4 0.89(3) 2.43(3) 3.246(3) 152(2) . yes

_refine_diff_density_max         0.306
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.070


# start Validation Reply Form
_vrf_RINTA01_2_300K              
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: Crystals were of low quality and showed poor diffracting
power. This led to low quality data and a high Rint, despite several attempts
on different crystals were performed. All the results are in agreement with
the remaining analytical data.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_110K
_database_code_depnum_ccdc_archive 'CCDC 2310297'
loop_
_audit_author_name
_audit_author_address
'Clara S. B. Gomes'
;LAQV REQUIMTE, FCT, Universidade NOVA de Lisboa
Portugal
;
_audit_update_record             
;
2023-11-25 deposited with the CCDC.	2024-04-26 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         'C22 H28 F2 Fe N4 O2, Cl O4'
_chemical_formula_sum            'C22 H28 Cl F2 Fe N4 O6'
_chemical_formula_weight         573.78

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'
F F 0.0171 0.0103 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.8076(5)
_cell_length_b                   21.5134(10)
_cell_length_c                   12.1084(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.487(2)
_cell_angle_gamma                90
_cell_volume                     2473.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9699
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_F_000             1188
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.779
_shelx_estimated_absorpt_T_min   0.860
_shelx_estimated_absorpt_T_max   0.886
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36275
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_av_R_equivalents  0.0799
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.861
_diffrn_reflns_theta_max         25.072
_diffrn_reflns_theta_full        25.072
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4389
_reflns_number_gt                3416
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    Mercury
_computing_publication_material  'WinGX and enCIFer'
_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)+(0.0452P)²+1.7498P] 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         4389
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.32464(4) 0.62282(2) 0.72839(3) 0.01558(12) Uani 1 1 d . . . . .
Cl1 Cl 0.27611(9) 0.59432(3) 1.12276(6) 0.0353(2) Uani 1 1 d . . . . .
F2 F -0.15449(18) 0.75559(7) 0.26627(14) 0.0304(4) Uani 1 1 d . . . . .
F1 F 0.85849(17) 0.53759(8) 0.48943(15) 0.0340(4) Uani 1 1 d . . . . .
O1 O 0.46689(18) 0.65574(8) 0.66791(16) 0.0200(4) Uani 1 1 d . . . . .
O2 O 0.20832(18) 0.60430(8) 0.58483(15) 0.0181(4) Uani 1 1 d . . . . .
O5 O 0.2405(2) 0.64280(9) 1.03928(18) 0.0346(5) Uani 1 1 d . . . . .
N3 N 0.2523(2) 0.70605(10) 0.72913(19) 0.0168(5) Uani 1 1 d . . . . .
N1 N 0.3928(2) 0.53877(10) 0.72827(18) 0.0169(5) Uani 1 1 d . . . . .
N2 N 0.1798(2) 0.58274(10) 0.8018(2) 0.0176(5) Uani 1 1 d . . . . .
N4 N 0.4461(2) 0.64640(11) 0.8857(2) 0.0193(5) Uani 1 1 d . . . . .
C1 C 0.5555(3) 0.62423(12) 0.6234(2) 0.0163(6) Uani 1 1 d . . . . .
O4 O 0.3298(3) 0.54296(11) 1.0701(2) 0.0597(8) Uani 1 1 d . . . . .
C18 C 0.1643(3) 0.73340(12) 0.6474(2) 0.0189(6) Uani 1 1 d . . . . .
H18 H 0.139515 0.774131 0.659269 0.023 Uiso 1 1 calc R U . . .
C7 C 0.4859(3) 0.51931(12) 0.6783(2) 0.0180(6) Uani 1 1 d . . . . .
H7 H 0.500835 0.476664 0.676782 0.022 Uiso 1 1 calc R U . . .
C6 C 0.5679(3) 0.55860(12) 0.6249(2) 0.0161(6) Uani 1 1 d . . . . .
C5 C 0.6699(3) 0.52996(13) 0.5783(2) 0.0200(6) Uani 1 1 d . . . . .
H5 H 0.678821 0.486916 0.579485 0.024 Uiso 1 1 calc R U . . .
C17 C 0.1010(3) 0.70552(12) 0.5387(2) 0.0180(6) Uani 1 1 d . . . . .
C2 C 0.6478(3) 0.65852(13) 0.5740(2) 0.0230(6) Uani 1 1 d . . . . .
H2 H 0.642046 0.701669 0.572639 0.028 Uiso 1 1 calc R U . . .
C3 C 0.7458(3) 0.62997(14) 0.5279(2) 0.0250(7) Uani 1 1 d . . . . .
H3 H 0.804865 0.653337 0.494866 0.030 Uiso 1 1 calc R U . . .
C4 C 0.7552(3) 0.56562(13) 0.5314(2) 0.0234(6) Uani 1 1 d . . . . .
C12 C 0.1305(3) 0.64384(12) 0.5121(2) 0.0185(6) Uani 1 1 d . . . . .
C19 C 0.3083(3) 0.73996(13) 0.8364(2) 0.0233(6) Uani 1 1 d . . . . .
H19A H 0.249248 0.732977 0.888650 0.028 Uiso 1 1 calc R U . . .
H19B H 0.310951 0.784223 0.821853 0.028 Uiso 1 1 calc R U . . .
C16 C 0.0076(3) 0.74202(13) 0.4567(2) 0.0228(6) Uani 1 1 d . . . . .
H16 H -0.013608 0.782376 0.474267 0.027 Uiso 1 1 calc R U . . .
C14 C -0.0204(3) 0.65812(13) 0.3212(3) 0.0262(7) Uani 1 1 d . . . . .
H14 H -0.059727 0.642940 0.248211 0.031 Uiso 1 1 calc R U . . .
C10 C 0.0384(3) 0.61288(13) 0.7772(3) 0.0220(6) Uani 1 1 d . . . . .
H10A H -0.001756 0.612514 0.695417 0.026 Uiso 1 1 calc R U . . .
H10B H 0.050277 0.655966 0.801304 0.026 Uiso 1 1 calc R U . . .
O3 O 0.3798(4) 0.61650(12) 1.2184(2) 0.0840(12) Uani 1 1 d . . . . .
C8 C 0.3206(3) 0.49334(12) 0.7843(3) 0.0222(6) Uani 1 1 d . . . . .
H8A H 0.366965 0.490441 0.864850 0.027 Uiso 1 1 calc R U . . .
H8B H 0.321398 0.452596 0.750124 0.027 Uiso 1 1 calc R U . . .
C9 C 0.1711(3) 0.51604(12) 0.7680(2) 0.0209(6) Uani 1 1 d . . . . .
H9A H 0.119260 0.511500 0.688916 0.025 Uiso 1 1 calc R U . . .
H9B H 0.123418 0.492312 0.815276 0.025 Uiso 1 1 calc R U . . .
C15 C -0.0515(3) 0.71789(14) 0.3513(3) 0.0270(7) Uani 1 1 d . . . . .
C20 C 0.4545(3) 0.71577(12) 0.8867(3) 0.0242(7) Uani 1 1 d . . . . .
H20A H 0.517859 0.729719 0.841772 0.029 Uiso 1 1 calc R U . . .
H20B H 0.489423 0.730816 0.964117 0.029 Uiso 1 1 calc R U . . .
C13 C 0.0694(3) 0.62177(13) 0.4010(2) 0.0222(6) Uani 1 1 d . . . . .
H13 H 0.090334 0.581762 0.381251 0.027 Uiso 1 1 calc R U . . .
C21 C 0.5879(3) 0.61644(13) 0.9192(2) 0.0245(6) Uani 1 1 d . . . . .
H21A H 0.636177 0.624003 0.859680 0.029 Uiso 1 1 calc R U . . .
H21B H 0.575438 0.571878 0.924009 0.029 Uiso 1 1 calc R U . . .
C11 C -0.0643(3) 0.58237(14) 0.8348(3) 0.0302(7) Uani 1 1 d . . . . .
H11A H -0.086884 0.541491 0.803807 0.045 Uiso 1 1 calc R U . . .
H11B H -0.148667 0.606848 0.821793 0.045 Uiso 1 1 calc R U . . .
H11C H -0.022604 0.579402 0.915239 0.045 Uiso 1 1 calc R U . . .
O6 O 0.1532(4) 0.57702(15) 1.1557(3) 0.0965(13) Uani 1 1 d . . . . .
C22 C 0.6797(3) 0.63905(14) 1.0311(3) 0.0310(7) Uani 1 1 d . . . . .
H22A H 0.709551 0.680871 1.022387 0.047 Uiso 1 1 calc R U . . .
H22B H 0.760765 0.612631 1.053965 0.047 Uiso 1 1 calc R U . . .
H22C H 0.627280 0.638058 1.088261 0.047 Uiso 1 1 calc R U . . .
H4 H 0.405(3) 0.6378(13) 0.938(2) 0.016(7) Uiso 1 1 d . . . . .
H2B H 0.207(3) 0.5843(12) 0.871(3) 0.013(8) 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 1.8681(18) . ?
Fe1 O1 1.8697(18) . ?
Fe1 N3 1.927(2) . ?
Fe1 N1 1.928(2) . ?
Fe1 N4 2.042(2) . ?
Fe1 N2 2.045(2) . ?
Cl1 O6 1.411(3) . ?
Cl1 O3 1.419(3) . ?
Cl1 O5 1.434(2) . ?
Cl1 O4 1.440(2) . ?
F2 C15 1.489(3) . ?
F1 C4 1.380(3) . ?
O1 C1 1.319(3) . ?
O2 C12 1.321(3) . ?
N3 C18 1.282(3) . ?
N3 C19 1.471(3) . ?
N1 C7 1.285(3) . ?
N1 C8 1.469(3) . ?
N2 C9 1.489(3) . ?
N2 C10 1.492(3) . ?
N2 H2B 0.81(3) . ?
N4 C21 1.494(3) . ?
N4 C20 1.494(3) . ?
N4 H4 0.86(3) . ?
C1 C2 1.412(4) . ?
C1 C6 1.417(4) . ?
C18 C17 1.439(4) . ?
C18 H18 0.9300 . ?
C7 C6 1.428(4) . ?
C7 H7 0.9300 . ?
C6 C5 1.408(4) . ?
C5 C4 1.360(4) . ?
C5 H5 0.9300 . ?
C17 C16 1.409(4) . ?
C17 C12 1.412(4) . ?
C2 C3 1.371(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(4) . ?
C3 H3 0.9300 . ?
C12 C13 1.411(4) . ?
C19 C20 1.503(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C16 C15 1.365(4) . ?
C16 H16 0.9300 . ?
C14 C13 1.377(4) . ?
C14 C15 1.391(4) . ?
C14 H14 0.9300 . ?
C10 C11 1.511(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C8 C9 1.511(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C13 H13 0.9300 . ?
C21 C22 1.508(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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 O1 93.33(8) . . ?
O2 Fe1 N3 93.59(8) . . ?
O1 Fe1 N3 87.79(8) . . ?
O2 Fe1 N1 86.01(8) . . ?
O1 Fe1 N1 93.56(8) . . ?
N3 Fe1 N1 178.61(9) . . ?
O2 Fe1 N4 177.43(8) . . ?
O1 Fe1 N4 87.30(9) . . ?
N3 Fe1 N4 83.93(9) . . ?
N1 Fe1 N4 96.45(9) . . ?
O2 Fe1 N2 89.17(9) . . ?
O1 Fe1 N2 175.86(9) . . ?
N3 Fe1 N2 95.35(9) . . ?
N1 Fe1 N2 83.31(9) . . ?
N4 Fe1 N2 90.35(10) . . ?
O6 Cl1 O3 110.3(2) . . ?
O6 Cl1 O5 108.46(19) . . ?
O3 Cl1 O5 109.22(16) . . ?
O6 Cl1 O4 110.85(19) . . ?
O3 Cl1 O4 110.67(17) . . ?
O5 Cl1 O4 107.30(14) . . ?
C1 O1 Fe1 126.71(16) . . ?
C12 O2 Fe1 126.83(17) . . ?
C18 N3 C19 119.0(2) . . ?
C18 N3 Fe1 126.92(19) . . ?
C19 N3 Fe1 114.11(16) . . ?
C7 N1 C8 118.8(2) . . ?
C7 N1 Fe1 126.39(18) . . ?
C8 N1 Fe1 114.61(16) . . ?
C9 N2 C10 112.2(2) . . ?
C9 N2 Fe1 106.59(16) . . ?
C10 N2 Fe1 116.25(17) . . ?
C9 N2 H2B 107.7(19) . . ?
C10 N2 H2B 103.7(19) . . ?
Fe1 N2 H2B 110.2(19) . . ?
C21 N4 C20 112.5(2) . . ?
C21 N4 Fe1 115.61(18) . . ?
C20 N4 Fe1 105.87(17) . . ?
C21 N4 H4 106.5(19) . . ?
C20 N4 H4 104.2(18) . . ?
Fe1 N4 H4 111.6(19) . . ?
O1 C1 C2 117.6(2) . . ?
O1 C1 C6 124.8(2) . . ?
C2 C1 C6 117.6(2) . . ?
N3 C18 C17 124.6(2) . . ?
N3 C18 H18 117.7 . . ?
C17 C18 H18 117.7 . . ?
N1 C7 C6 124.6(2) . . ?
N1 C7 H7 117.7 . . ?
C6 C7 H7 117.7 . . ?
C5 C6 C1 119.9(2) . . ?
C5 C6 C7 117.4(2) . . ?
C1 C6 C7 122.6(2) . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C16 C17 C12 119.8(3) . . ?
C16 C17 C18 117.9(2) . . ?
C12 C17 C18 122.3(2) . . ?
C3 C2 C1 121.8(3) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 118.9(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 F1 119.5(2) . . ?
C5 C4 C3 122.2(3) . . ?
F1 C4 C3 118.3(2) . . ?
O2 C12 C13 117.1(2) . . ?
O2 C12 C17 124.8(2) . . ?
C13 C12 C17 118.1(3) . . ?
N3 C19 C20 107.0(2) . . ?
N3 C19 H19A 110.3 . . ?
C20 C19 H19A 110.3 . . ?
N3 C19 H19B 110.3 . . ?
C20 C19 H19B 110.3 . . ?
H19A C19 H19B 108.6 . . ?
C15 C16 C17 119.7(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C13 C14 C15 119.0(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
N2 C10 C11 114.4(2) . . ?
N2 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
N2 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
N1 C8 C9 106.8(2) . . ?
N1 C8 H8A 110.4 . . ?
C9 C8 H8A 110.4 . . ?
N1 C8 H8B 110.4 . . ?
C9 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
N2 C9 C8 106.8(2) . . ?
N2 C9 H9A 110.4 . . ?
C8 C9 H9A 110.4 . . ?
N2 C9 H9B 110.4 . . ?
C8 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
C16 C15 C14 121.8(3) . . ?
C16 C15 F2 119.7(3) . . ?
C14 C15 F2 118.5(2) . . ?
N4 C20 C19 107.3(2) . . ?
N4 C20 H20A 110.3 . . ?
C19 C20 H20A 110.3 . . ?
N4 C20 H20B 110.3 . . ?
C19 C20 H20B 110.3 . . ?
H20A C20 H20B 108.5 . . ?
C14 C13 C12 121.5(3) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
N4 C21 C22 114.3(2) . . ?
N4 C21 H21A 108.7 . . ?
C22 C21 H21A 108.7 . . ?
N4 C21 H21B 108.7 . . ?
C22 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Fe1 O1 C1 -74.5(2) . . . . ?
N3 Fe1 O1 C1 -168.0(2) . . . . ?
N1 Fe1 O1 C1 11.7(2) . . . . ?
N4 Fe1 O1 C1 108.0(2) . . . . ?
O1 Fe1 O2 C12 -77.2(2) . . . . ?
N3 Fe1 O2 C12 10.7(2) . . . . ?
N1 Fe1 O2 C12 -170.6(2) . . . . ?
N2 Fe1 O2 C12 106.1(2) . . . . ?
Fe1 O1 C1 C2 174.98(18) . . . . ?
Fe1 O1 C1 C6 -7.3(4) . . . . ?
C19 N3 C18 C17 -179.6(2) . . . . ?
Fe1 N3 C18 C17 1.0(4) . . . . ?
C8 N1 C7 C6 -177.2(2) . . . . ?
Fe1 N1 C7 C6 7.9(4) . . . . ?
O1 C1 C6 C5 -177.7(2) . . . . ?
C2 C1 C6 C5 0.0(4) . . . . ?
O1 C1 C6 C7 -1.4(4) . . . . ?
C2 C1 C6 C7 176.4(2) . . . . ?
N1 C7 C6 C5 177.3(2) . . . . ?
N1 C7 C6 C1 0.9(4) . . . . ?
C1 C6 C5 C4 -0.4(4) . . . . ?
C7 C6 C5 C4 -176.9(2) . . . . ?
N3 C18 C17 C16 -179.0(2) . . . . ?
N3 C18 C17 C12 0.5(4) . . . . ?
O1 C1 C2 C3 178.5(2) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C6 C5 C4 F1 177.7(2) . . . . ?
C6 C5 C4 C3 0.1(4) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C2 C3 C4 F1 -177.1(2) . . . . ?
Fe1 O2 C12 C13 169.53(17) . . . . ?
Fe1 O2 C12 C17 -12.5(4) . . . . ?
C16 C17 C12 O2 -175.1(2) . . . . ?
C18 C17 C12 O2 5.5(4) . . . . ?
C16 C17 C12 C13 2.9(4) . . . . ?
C18 C17 C12 C13 -176.5(2) . . . . ?
C18 N3 C19 C20 -149.3(2) . . . . ?
Fe1 N3 C19 C20 30.2(3) . . . . ?
C12 C17 C16 C15 -1.3(4) . . . . ?
C18 C17 C16 C15 178.2(2) . . . . ?
C9 N2 C10 C11 58.0(3) . . . . ?
Fe1 N2 C10 C11 -179.0(2) . . . . ?
C7 N1 C8 C9 -144.8(2) . . . . ?
Fe1 N1 C8 C9 30.7(3) . . . . ?
C10 N2 C9 C8 173.5(2) . . . . ?
Fe1 N2 C9 C8 45.2(2) . . . . ?
N1 C8 C9 N2 -49.2(3) . . . . ?
C17 C16 C15 C14 -1.1(4) . . . . ?
C17 C16 C15 F2 177.6(2) . . . . ?
C13 C14 C15 C16 1.9(4) . . . . ?
C13 C14 C15 F2 -176.9(2) . . . . ?
C21 N4 C20 C19 172.3(2) . . . . ?
Fe1 N4 C20 C19 45.2(2) . . . . ?
N3 C19 C20 N4 -49.2(3) . . . . ?
C15 C14 C13 C12 -0.1(4) . . . . ?
O2 C12 C13 C14 175.9(2) . . . . ?
C17 C12 C13 C14 -2.2(4) . . . . ?
C20 N4 C21 C22 53.1(3) . . . . ?
Fe1 N4 C21 C22 174.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C18 H18 O5 0.93 2.65 3.140(3) 113.8 4_575
C7 H7 O3 0.93 2.50 3.319(4) 146.8 3_667
C19 H19B O3 0.97 2.65 3.545(4) 154.1 4_575
C9 H9A F1 0.97 2.46 3.268(3) 140.3 3_666
C21 H21A O1 0.97 2.59 3.094(3) 112.8 .
C21 H21B O4 0.97 2.63 3.518(4) 151.6 3_667
N4 H4 Cl1 0.86(3) 2.98(3) 3.830(3) 174(2) .
N4 H4 O5 0.86(3) 2.26(3) 3.067(3) 158(3) .
N2 H2B Cl1 0.81(3) 2.96(3) 3.772(3) 174(2) .
N2 H2B O5 0.81(3) 2.35(3) 3.072(3) 149(2) .
N2 H2B O4 0.81(3) 2.57(3) 3.326(3) 155(2) .

_refine_diff_density_max         0.607
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.073

