# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 2035917'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2020-10-07 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;
_audit_creation_date             2020-10-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 Cl5 Fe N3 O2'
_chemical_formula_sum            'C19 H17 Cl5 Fe N3 O2'
_chemical_formula_weight         552.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.3482(3)
_cell_length_b                   9.4215(2)
_cell_length_c                   25.8019(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.432(2)
_cell_angle_gamma                90
_cell_volume                     2265.68(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18316
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.76
_cell_measurement_theta_min      3.44
_shelx_estimated_absorpt_T_max   0.353
_shelx_estimated_absorpt_T_min   0.243
_exptl_absorpt_coefficient_mu    10.954
_exptl_absorpt_correction_T_max  0.0746
_exptl_absorpt_correction_T_min  0.0206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1116
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            24267
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         72.022
_diffrn_reflns_theta_min         3.436
_diffrn_ambient_temperature      293
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari with Xenocs Genix3D Cu HF'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3197
_reflns_number_total             4377
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction        
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.84, Darmstadt 2018
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4377
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0518P)²+0.9283P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1053
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C13(H13), C15(H15), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.57871(5) 0.70410(5) 0.38262(2) 0.03632(14) Uani 1 1 d . . . . .
Cl1 Cl 0.67790(10) 0.51094(10) 0.34100(4) 0.0563(2) Uani 1 1 d . . . . .
Cl2 Cl 0.15502(10) 0.43126(10) 0.38637(3) 0.0546(2) Uani 1 1 d . . . . .
Cl3 Cl -0.07059(10) 0.64727(12) 0.20598(4) 0.0623(3) Uani 1 1 d . . . . .
Cl4 Cl 0.25845(12) 1.05954(11) 0.41379(4) 0.0721(3) Uani 1 1 d . . . . .
Cl5 Cl 0.14437(12) 0.81337(11) 0.59298(5) 0.0735(3) Uani 1 1 d . . . . .
O1 O 0.3899(2) 0.6259(2) 0.37351(8) 0.0448(6) Uani 1 1 d . . . . .
O2 O 0.5079(2) 0.8706(2) 0.41949(8) 0.0416(5) Uani 1 1 d . . . . .
N1 N 0.5359(3) 0.8214(3) 0.31419(11) 0.0453(7) Uani 1 1 d . . . . .
N2 N 0.7810(3) 0.8191(3) 0.37989(11) 0.0452(7) Uani 1 1 d . . . . .
H2 H 0.771315 0.906023 0.400206 0.054 Uiso 1 1 calc R U . . .
N3 N 0.6571(3) 0.6439(3) 0.45808(10) 0.0374(6) Uani 1 1 d . . . . .
C1 C 0.2928(3) 0.6309(3) 0.33419(12) 0.0365(7) Uani 1 1 d . . . . .
C2 C 0.1700(3) 0.5447(3) 0.33443(12) 0.0362(7) Uani 1 1 d . . . . .
C3 C 0.0604(3) 0.5488(4) 0.29565(12) 0.0415(8) Uani 1 1 d . . . . .
H3 H -0.019428 0.490473 0.297246 0.050 Uiso 1 1 calc R U . . .
C4 C 0.0704(3) 0.6407(4) 0.25426(13) 0.0417(8) Uani 1 1 d . . . . .
C5 C 0.1882(4) 0.7247(4) 0.25108(13) 0.0434(8) Uani 1 1 d . . . . .
H5 H 0.194130 0.784540 0.222660 0.052 Uiso 1 1 calc R U . . .
C6 C 0.3011(3) 0.7215(3) 0.29062(12) 0.0388(7) Uani 1 1 d . . . . .
C7 C 0.4220(4) 0.8144(4) 0.28391(14) 0.0472(8) Uani 1 1 d . . . . .
H7 H 0.415813 0.873869 0.255050 0.057 Uiso 1 1 calc R U . . .
C8 C 0.6480(4) 0.9253(4) 0.30472(16) 0.0614(11) Uani 1 1 d . . . . .
H8A H 0.629821 1.013968 0.322169 0.074 Uiso 1 1 calc R U . . .
H8B H 0.648858 0.943881 0.267769 0.074 Uiso 1 1 calc R U . . .
C9 C 0.7906(4) 0.8645(5) 0.32550(15) 0.0603(10) Uani 1 1 d . . . . .
H9A H 0.815173 0.784069 0.304492 0.072 Uiso 1 1 calc R U . . .
H9B H 0.865061 0.935701 0.323827 0.072 Uiso 1 1 calc R U . . .
C10 C 0.9153(4) 0.7497(4) 0.40114(16) 0.0567(10) Uani 1 1 d . . . . .
H10A H 0.994040 0.816093 0.399238 0.068 Uiso 1 1 calc R U . . .
H10B H 0.934410 0.668911 0.379400 0.068 Uiso 1 1 calc R U . . .
C11 C 0.9120(4) 0.6993(4) 0.45687(15) 0.0509(9) Uani 1 1 d . . . . .
H11A H 0.892165 0.780252 0.478400 0.061 Uiso 1 1 calc R U . . .
H11B H 1.006691 0.664309 0.468532 0.061 Uiso 1 1 calc R U . . .
C12 C 0.8024(3) 0.5832(3) 0.46584(13) 0.0425(8) Uani 1 1 d . . . . .
H12A H 0.812652 0.505672 0.441641 0.051 Uiso 1 1 calc R U . . .
H12B H 0.818487 0.546212 0.500893 0.051 Uiso 1 1 calc R U . . .
C13 C 0.5884(3) 0.6675(3) 0.49829(12) 0.0376(7) Uani 1 1 d . . . . .
H13 H 0.623703 0.627173 0.529600 0.045 Uiso 1 1 calc R U . . .
C14 C 0.4592(3) 0.7530(3) 0.49832(12) 0.0361(7) Uani 1 1 d . . . . .
C15 C 0.3756(4) 0.7436(4) 0.54055(14) 0.0445(8) Uani 1 1 d . . . . .
H15 H 0.401265 0.681789 0.567800 0.053 Uiso 1 1 calc R U . . .
C16 C 0.2546(4) 0.8264(4) 0.54165(15) 0.0488(9) Uani 1 1 d . . . . .
C17 C 0.2187(4) 0.9223(4) 0.50250(16) 0.0506(9) Uani 1 1 d . . . . .
H17 H 0.136199 0.977015 0.503547 0.061 Uiso 1 1 calc R U . . .
C18 C 0.3033(4) 0.9373(3) 0.46235(14) 0.0455(8) Uani 1 1 d . . . . .
C19 C 0.4277(3) 0.8532(3) 0.45767(13) 0.0373(7) Uani 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 Cl1 2.3407(10) . ?
Fe1 O1 1.911(2) . ?
Fe1 O2 1.975(2) . ?
Fe1 N1 2.095(3) . ?
Fe1 N2 2.185(3) . ?
Fe1 N3 2.104(3) . ?
Cl2 C2 1.728(3) . ?
Cl3 C4 1.743(3) . ?
Cl4 C18 1.730(4) . ?
Cl5 C16 1.744(4) . ?
O1 C1 1.309(4) . ?
O2 C19 1.293(4) . ?
N1 C7 1.272(4) . ?
N1 C8 1.468(4) . ?
N2 H2 0.9800 . ?
N2 C9 1.476(5) . ?
N2 C10 1.483(4) . ?
N3 C12 1.474(4) . ?
N3 C13 1.281(4) . ?
C1 C2 1.406(4) . ?
C1 C6 1.418(4) . ?
C2 C3 1.377(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(5) . ?
C4 C5 1.364(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.410(4) . ?
C6 C7 1.451(5) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.510(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.517(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.529(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13 0.9300 . ?
C13 C14 1.452(4) . ?
C14 C15 1.392(4) . ?
C14 C19 1.425(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.376(5) . ?
C16 C17 1.377(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.358(5) . ?
C18 C19 1.420(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Fe1 Cl1 92.23(8) . . ?
O1 Fe1 O2 91.40(10) . . ?
O1 Fe1 N1 89.15(10) . . ?
O1 Fe1 N2 168.76(10) . . ?
O1 Fe1 N3 105.20(10) . . ?
O2 Fe1 Cl1 176.24(7) . . ?
O2 Fe1 N1 86.42(10) . . ?
O2 Fe1 N2 86.83(10) . . ?
O2 Fe1 N3 82.76(9) . . ?
N1 Fe1 Cl1 94.60(9) . . ?
N1 Fe1 N2 79.67(11) . . ?
N1 Fe1 N3 162.17(11) . . ?
N2 Fe1 Cl1 89.79(8) . . ?
N3 Fe1 Cl1 95.34(7) . . ?
N3 Fe1 N2 85.60(10) . . ?
C1 O1 Fe1 131.3(2) . . ?
C19 O2 Fe1 120.1(2) . . ?
C7 N1 Fe1 125.9(2) . . ?
C7 N1 C8 120.4(3) . . ?
C8 N1 Fe1 113.5(2) . . ?
Fe1 N2 H2 106.3 . . ?
C9 N2 Fe1 106.9(2) . . ?
C9 N2 H2 106.3 . . ?
C9 N2 C10 111.6(3) . . ?
C10 N2 Fe1 118.6(2) . . ?
C10 N2 H2 106.3 . . ?
C12 N3 Fe1 118.8(2) . . ?
C13 N3 Fe1 122.8(2) . . ?
C13 N3 C12 118.2(3) . . ?
O1 C1 C2 119.5(3) . . ?
O1 C1 C6 124.0(3) . . ?
C2 C1 C6 116.5(3) . . ?
C1 C2 Cl2 118.4(2) . . ?
C3 C2 Cl2 118.7(2) . . ?
C3 C2 C1 122.8(3) . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 Cl3 118.8(3) . . ?
C5 C4 Cl3 120.4(3) . . ?
C5 C4 C3 120.8(3) . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 123.3(3) . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 C7 116.5(3) . . ?
N1 C7 C6 125.5(3) . . ?
N1 C7 H7 117.3 . . ?
C6 C7 H7 117.3 . . ?
N1 C8 H8A 110.1 . . ?
N1 C8 H8B 110.1 . . ?
N1 C8 C9 108.0(3) . . ?
H8A C8 H8B 108.4 . . ?
C9 C8 H8A 110.1 . . ?
C9 C8 H8B 110.1 . . ?
N2 C9 C8 109.3(3) . . ?
N2 C9 H9A 109.8 . . ?
N2 C9 H9B 109.8 . . ?
C8 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
N2 C10 H10A 108.7 . . ?
N2 C10 H10B 108.7 . . ?
N2 C10 C11 114.2(3) . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C10 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
C10 C11 C12 115.5(3) . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
N3 C12 C11 108.9(3) . . ?
N3 C12 H12A 109.9 . . ?
N3 C12 H12B 109.9 . . ?
C11 C12 H12A 109.9 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
N3 C13 H13 117.8 . . ?
N3 C13 C14 124.5(3) . . ?
C14 C13 H13 117.8 . . ?
C15 C14 C13 118.8(3) . . ?
C15 C14 C19 121.5(3) . . ?
C19 C14 C13 119.4(3) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.5(3) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 Cl5 120.7(3) . . ?
C15 C16 C17 120.7(3) . . ?
C17 C16 Cl5 118.6(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 Cl4 119.9(3) . . ?
C17 C18 C19 122.4(3) . . ?
C19 C18 Cl4 117.7(3) . . ?
O2 C19 C14 123.1(3) . . ?
O2 C19 C18 121.4(3) . . ?
C18 C19 C14 115.5(3) . . ?

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
Fe1 O1 C1 C2 169.8(2) . . . . ?
Fe1 O1 C1 C6 -11.6(5) . . . . ?
Fe1 O2 C19 C14 46.0(4) . . . . ?
Fe1 O2 C19 C18 -135.9(3) . . . . ?
Fe1 N1 C7 C6 -1.2(5) . . . . ?
Fe1 N1 C8 C9 33.3(4) . . . . ?
Fe1 N2 C9 C8 45.0(3) . . . . ?
Fe1 N2 C10 C11 -54.6(4) . . . . ?
Fe1 N3 C12 C11 68.9(3) . . . . ?
Fe1 N3 C13 C14 -8.1(4) . . . . ?
Cl2 C2 C3 C4 179.1(2) . . . . ?
Cl3 C4 C5 C6 178.8(3) . . . . ?
Cl4 C18 C19 O2 2.4(4) . . . . ?
Cl4 C18 C19 C14 -179.3(2) . . . . ?
Cl5 C16 C17 C18 178.8(3) . . . . ?
O1 C1 C2 Cl2 -1.7(4) . . . . ?
O1 C1 C2 C3 177.0(3) . . . . ?
O1 C1 C6 C5 -177.0(3) . . . . ?
O1 C1 C6 C7 2.8(5) . . . . ?
N1 C8 C9 N2 -52.2(4) . . . . ?
N2 C10 C11 C12 63.8(4) . . . . ?
N3 C13 C14 C15 164.7(3) . . . . ?
N3 C13 C14 C19 -20.8(5) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C1 C6 C7 N1 3.4(6) . . . . ?
C2 C1 C6 C5 1.7(5) . . . . ?
C2 C1 C6 C7 -178.5(3) . . . . ?
C2 C3 C4 Cl3 -178.9(2) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C3 C4 C5 C6 -1.3(5) . . . . ?
C4 C5 C6 C1 -0.2(5) . . . . ?
C4 C5 C6 C7 180.0(3) . . . . ?
C5 C6 C7 N1 -176.7(3) . . . . ?
C6 C1 C2 Cl2 179.5(2) . . . . ?
C6 C1 C2 C3 -1.8(5) . . . . ?
C7 N1 C8 C9 -150.7(3) . . . . ?
C8 N1 C7 C6 -176.8(3) . . . . ?
C9 N2 C10 C11 -179.5(3) . . . . ?
C10 N2 C9 C8 176.2(3) . . . . ?
C10 C11 C12 N3 -69.2(4) . . . . ?
C12 N3 C13 C14 166.5(3) . . . . ?
C13 N3 C12 C11 -106.0(3) . . . . ?
C13 C14 C15 C16 178.5(3) . . . . ?
C13 C14 C19 O2 1.4(5) . . . . ?
C13 C14 C19 C18 -176.8(3) . . . . ?
C14 C15 C16 Cl5 178.0(3) . . . . ?
C14 C15 C16 C17 -2.6(5) . . . . ?
C15 C14 C19 O2 175.8(3) . . . . ?
C15 C14 C19 C18 -2.4(4) . . . . ?
C15 C16 C17 C18 -0.6(5) . . . . ?
C16 C17 C18 Cl4 -179.2(3) . . . . ?
C16 C17 C18 C19 2.3(5) . . . . ?
C17 C18 C19 O2 -179.0(3) . . . . ?
C17 C18 C19 C14 -0.8(5) . . . . ?
C19 C14 C15 C16 4.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_1d_HS
_database_code_depnum_ccdc_archive 'CCDC 2035919'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2020-10-07 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;
_audit_creation_date             2020-10-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 Cl4 Fe N4 O2 Se'
_chemical_formula_sum            'C20 H17 Cl4 Fe N4 O2 Se'
_chemical_formula_weight         621.99
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.4121(3)
_cell_length_b                   23.8983(6)
_cell_length_c                   12.1650(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.571(3)
_cell_angle_gamma                90
_cell_volume                     2344.02(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    44029
_cell_measurement_temperature    200
_cell_measurement_theta_max      72.24
_cell_measurement_theta_min      3.70
_shelx_estimated_absorpt_T_max   0.659
_shelx_estimated_absorpt_T_min   0.163
_exptl_absorpt_coefficient_mu    11.360
_exptl_absorpt_correction_T_max  0.1929
_exptl_absorpt_correction_T_min  0.0328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1236
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            43322
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         5.301
_diffrn_ambient_temperature      200
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari with Xenocs Genix3D Cu HF'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3373
_reflns_number_total             4109
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction        
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.84, Darmstadt 2018
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         2.159
_refine_diff_density_min         -0.697
_refine_diff_density_rms         0.247
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0906
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1711P)²+6.6127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2388
_refine_ls_wR_factor_ref         0.2605
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C13(H13), C15(H15), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Se1 Se 0.36513(13) 0.66786(4) 0.32233(8) 0.0626(4) Uani 1 1 d . . . . .
Fe1 Fe 0.46796(14) 0.60353(5) 0.71398(10) 0.0431(4) Uani 1 1 d . . . . .
Cl1 Cl -0.0492(2) 0.57083(8) 0.44954(18) 0.0561(5) Uani 1 1 d . . . . .
Cl2 Cl -0.2697(3) 0.77808(10) 0.5020(2) 0.0719(7) Uani 1 1 d . . . . .
Cl3 Cl 0.2240(2) 0.57366(8) 1.01059(17) 0.0522(5) Uani 1 1 d . . . . .
Cl4 Cl 0.1174(3) 0.35788(8) 0.8861(2) 0.0632(6) Uani 1 1 d . . . . .
O1 O 0.2353(6) 0.6029(2) 0.6347(5) 0.0480(12) Uani 1 1 d . . . . .
O2 O 0.4358(6) 0.5733(2) 0.8556(4) 0.0454(12) Uani 1 1 d . . . . .
N1 N 0.4401(8) 0.6845(3) 0.7701(5) 0.0462(14) Uani 1 1 d . . . . .
N2 N 0.7259(8) 0.6255(3) 0.8016(6) 0.0500(15) Uani 1 1 d . . . . .
H2 H 0.752388 0.608246 0.879617 0.060 Uiso 1 1 calc R U . . .
N3 N 0.5604(8) 0.5241(3) 0.6935(5) 0.0491(15) Uani 1 1 d . . . . .
N4 N 0.5078(9) 0.6324(3) 0.5616(6) 0.0540(16) Uani 1 1 d . . . . .
C1 C 0.1328(9) 0.6449(3) 0.6018(6) 0.0428(16) Uani 1 1 d . . . . .
C2 C -0.0168(9) 0.6366(3) 0.5136(6) 0.0433(16) Uani 1 1 d . . . . .
C3 C -0.1397(10) 0.6761(3) 0.4801(7) 0.0487(17) Uani 1 1 d . . . . .
H3 H -0.238856 0.668973 0.420663 0.058 Uiso 1 1 calc R U . . .
C4 C -0.1110(10) 0.7276(3) 0.5386(7) 0.0500(18) Uani 1 1 d . . . . .
C5 C 0.0331(10) 0.7397(3) 0.6179(7) 0.0483(17) Uani 1 1 d . . . . .
H5 H 0.050053 0.775857 0.651802 0.058 Uiso 1 1 calc R U . . .
C6 C 0.1595(9) 0.6986(3) 0.6508(6) 0.0436(16) Uani 1 1 d . . . . .
C7 C 0.3100(10) 0.7154(3) 0.7352(7) 0.0480(17) Uani 1 1 d . . . . .
H7 H 0.313477 0.751719 0.767366 0.058 Uiso 1 1 calc R U . . .
C8 C 0.5890(10) 0.7058(3) 0.8552(7) 0.0541(19) Uani 1 1 d . . . . .
H8A H 0.595048 0.691051 0.932348 0.065 Uiso 1 1 calc R U . . .
H8B H 0.586227 0.747183 0.858019 0.065 Uiso 1 1 calc R U . . .
C9 C 0.7357(10) 0.6865(4) 0.8186(7) 0.0542(19) Uani 1 1 d . . . . .
H9A H 0.736602 0.705286 0.746283 0.065 Uiso 1 1 calc R U . . .
H9B H 0.839509 0.696241 0.878070 0.065 Uiso 1 1 calc R U . . .
C10 C 0.8534(11) 0.6051(4) 0.7485(8) 0.059(2) Uani 1 1 d . . . . .
H10A H 0.963746 0.616491 0.798089 0.071 Uiso 1 1 calc R U . . .
H10B H 0.836177 0.624222 0.673790 0.071 Uiso 1 1 calc R U . . .
C11 C 0.8559(10) 0.5433(4) 0.7290(7) 0.060(2) Uani 1 1 d . . . . .
H11A H 0.872361 0.524132 0.803501 0.073 Uiso 1 1 calc R U . . .
H11B H 0.952573 0.534430 0.701032 0.073 Uiso 1 1 calc R U . . .
C12 C 0.7004(10) 0.5196(4) 0.6440(7) 0.0543(19) Uani 1 1 d . . . . .
H12A H 0.675442 0.540732 0.571085 0.065 Uiso 1 1 calc R U . . .
H12B H 0.718728 0.479935 0.627706 0.065 Uiso 1 1 calc R U . . .
C13 C 0.5102(10) 0.4796(3) 0.7302(7) 0.0499(18) Uani 1 1 d . . . . .
H13 H 0.551659 0.445029 0.711304 0.060 Uiso 1 1 calc R U . . .
C14 C 0.3926(10) 0.4774(3) 0.7999(7) 0.0483(17) Uani 1 1 d . . . . .
C15 C 0.3227(10) 0.4258(3) 0.8116(6) 0.0493(18) Uani 1 1 d . . . . .
H15 H 0.348989 0.393829 0.773742 0.059 Uiso 1 1 calc R U . . .
C16 C 0.2158(10) 0.4210(3) 0.8776(7) 0.0491(17) Uani 1 1 d . . . . .
C17 C 0.1867(9) 0.4672(3) 0.9385(6) 0.0463(17) Uani 1 1 d . . . . .
H17 H 0.113738 0.463889 0.985058 0.056 Uiso 1 1 calc R U . . .
C18 C 0.2610(9) 0.5166(3) 0.9321(6) 0.0433(16) Uani 1 1 d . . . . .
C19 C 0.3671(9) 0.5254(3) 0.8610(6) 0.0414(15) Uani 1 1 d . . . . .
C20 C 0.4532(10) 0.6465(3) 0.4705(8) 0.0506(18) Uani 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
Se1 C20 1.815(9) . ?
Fe1 O1 1.919(5) . ?
Fe1 O2 1.956(5) . ?
Fe1 N1 2.086(7) . ?
Fe1 N2 2.190(6) . ?
Fe1 N3 2.094(6) . ?
Fe1 N4 2.092(6) . ?
Cl1 C2 1.741(7) . ?
Cl2 C4 1.759(7) . ?
Cl3 C18 1.743(7) . ?
Cl4 C16 1.739(8) . ?
O1 C1 1.309(9) . ?
O2 C19 1.293(9) . ?
N1 C7 1.288(10) . ?
N1 C8 1.470(10) . ?
N2 H2 1.0000 . ?
N2 C9 1.472(11) . ?
N2 C10 1.483(11) . ?
N3 C12 1.471(10) . ?
N3 C13 1.271(10) . ?
N4 C20 1.124(10) . ?
C1 C2 1.416(11) . ?
C1 C6 1.407(10) . ?
C2 C3 1.373(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.409(11) . ?
C4 C5 1.348(12) . ?
C5 H5 0.9500 . ?
C5 C6 1.419(10) . ?
C6 C7 1.440(11) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.500(12) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.497(14) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.526(13) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13 0.9500 . ?
C13 C14 1.477(11) . ?
C14 C15 1.391(11) . ?
C14 C19 1.416(11) . ?
C15 H15 0.9500 . ?
C15 C16 1.371(12) . ?
C16 C17 1.388(11) . ?
C17 H17 0.9500 . ?
C17 C18 1.349(11) . ?
C18 C19 1.424(11) . ?

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 93.6(2) . . ?
O1 Fe1 N1 88.7(2) . . ?
O1 Fe1 N2 166.6(2) . . ?
O1 Fe1 N3 107.1(2) . . ?
O1 Fe1 N4 87.4(3) . . ?
O2 Fe1 N1 89.9(2) . . ?
O2 Fe1 N2 91.5(2) . . ?
O2 Fe1 N3 85.4(2) . . ?
O2 Fe1 N4 177.4(3) . . ?
N1 Fe1 N2 78.9(3) . . ?
N1 Fe1 N3 163.7(3) . . ?
N1 Fe1 N4 92.6(3) . . ?
N3 Fe1 N2 85.7(3) . . ?
N4 Fe1 N2 88.0(3) . . ?
N4 Fe1 N3 92.0(3) . . ?
C1 O1 Fe1 129.5(5) . . ?
C19 O2 Fe1 123.2(4) . . ?
C7 N1 Fe1 126.0(5) . . ?
C7 N1 C8 120.4(7) . . ?
C8 N1 Fe1 113.6(5) . . ?
Fe1 N2 H2 106.6 . . ?
C9 N2 Fe1 108.3(5) . . ?
C9 N2 H2 106.6 . . ?
C9 N2 C10 111.5(6) . . ?
C10 N2 Fe1 116.7(5) . . ?
C10 N2 H2 106.6 . . ?
C12 N3 Fe1 118.8(5) . . ?
C13 N3 Fe1 123.0(5) . . ?
C13 N3 C12 117.9(7) . . ?
C20 N4 Fe1 148.1(7) . . ?
O1 C1 C2 119.4(6) . . ?
O1 C1 C6 123.9(7) . . ?
C6 C1 C2 116.7(7) . . ?
C1 C2 Cl1 117.2(5) . . ?
C3 C2 Cl1 118.6(6) . . ?
C3 C2 C1 124.1(7) . . ?
C2 C3 H3 121.8 . . ?
C2 C3 C4 116.4(7) . . ?
C4 C3 H3 121.8 . . ?
C3 C4 Cl2 117.6(6) . . ?
C5 C4 Cl2 119.8(6) . . ?
C5 C4 C3 122.6(7) . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.2(7) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.7(7) . . ?
C1 C6 C7 123.9(7) . . ?
C5 C6 C7 116.4(7) . . ?
N1 C7 C6 124.6(7) . . ?
N1 C7 H7 117.7 . . ?
C6 C7 H7 117.7 . . ?
N1 C8 H8A 110.3 . . ?
N1 C8 H8B 110.3 . . ?
N1 C8 C9 107.0(6) . . ?
H8A C8 H8B 108.6 . . ?
C9 C8 H8A 110.3 . . ?
C9 C8 H8B 110.3 . . ?
N2 C9 C8 109.2(6) . . ?
N2 C9 H9A 109.8 . . ?
N2 C9 H9B 109.8 . . ?
C8 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
N2 C10 H10A 108.3 . . ?
N2 C10 H10B 108.3 . . ?
N2 C10 C11 115.9(7) . . ?
H10A C10 H10B 107.4 . . ?
C11 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
C10 C11 H11A 108.5 . . ?
C10 C11 H11B 108.5 . . ?
C10 C11 C12 115.2(7) . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
N3 C12 C11 109.1(7) . . ?
N3 C12 H12A 109.9 . . ?
N3 C12 H12B 109.9 . . ?
C11 C12 H12A 109.9 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
N3 C13 H13 117.4 . . ?
N3 C13 C14 125.2(7) . . ?
C14 C13 H13 117.4 . . ?
C15 C14 C13 117.5(7) . . ?
C15 C14 C19 122.2(7) . . ?
C19 C14 C13 119.9(7) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(7) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 Cl4 120.6(6) . . ?
C15 C16 C17 119.5(7) . . ?
C17 C16 Cl4 119.9(6) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.6(7) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 Cl3 119.7(6) . . ?
C17 C18 C19 123.0(7) . . ?
C19 C18 Cl3 117.3(5) . . ?
O2 C19 C14 123.6(7) . . ?
O2 C19 C18 121.9(6) . . ?
C14 C19 C18 114.4(7) . . ?
N4 C20 Se1 178.9(7) . . ?

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
Fe1 O1 C1 C2 159.2(5) . . . . ?
Fe1 O1 C1 C6 -22.3(10) . . . . ?
Fe1 O2 C19 C14 38.3(9) . . . . ?
Fe1 O2 C19 C18 -143.0(6) . . . . ?
Fe1 N1 C7 C6 0.4(10) . . . . ?
Fe1 N1 C8 C9 39.3(8) . . . . ?
Fe1 N2 C9 C8 41.6(7) . . . . ?
Fe1 N2 C10 C11 -55.7(9) . . . . ?
Fe1 N3 C12 C11 68.8(7) . . . . ?
Fe1 N3 C13 C14 -5.4(12) . . . . ?
Cl1 C2 C3 C4 176.8(6) . . . . ?
Cl2 C4 C5 C6 177.8(6) . . . . ?
Cl3 C18 C19 O2 1.0(9) . . . . ?
Cl3 C18 C19 C14 179.7(5) . . . . ?
Cl4 C16 C17 C18 -179.4(6) . . . . ?
O1 C1 C2 Cl1 -3.0(9) . . . . ?
O1 C1 C2 C3 173.6(7) . . . . ?
O1 C1 C6 C5 -173.2(7) . . . . ?
O1 C1 C6 C7 6.2(11) . . . . ?
N1 C8 C9 N2 -53.2(8) . . . . ?
N2 C10 C11 C12 64.0(10) . . . . ?
N3 C13 C14 C15 166.1(8) . . . . ?
N3 C13 C14 C19 -20.0(12) . . . . ?
C1 C2 C3 C4 0.3(11) . . . . ?
C1 C6 C7 N1 4.5(12) . . . . ?
C2 C1 C6 C5 5.4(10) . . . . ?
C2 C1 C6 C7 -175.2(7) . . . . ?
C2 C3 C4 Cl2 -177.4(6) . . . . ?
C2 C3 C4 C5 4.4(11) . . . . ?
C3 C4 C5 C6 -4.0(12) . . . . ?
C4 C5 C6 C1 -1.1(11) . . . . ?
C4 C5 C6 C7 179.4(7) . . . . ?
C5 C6 C7 N1 -176.1(7) . . . . ?
C6 C1 C2 Cl1 178.4(5) . . . . ?
C6 C1 C2 C3 -5.1(11) . . . . ?
C7 N1 C8 C9 -139.3(7) . . . . ?
C8 N1 C7 C6 178.9(7) . . . . ?
C9 N2 C10 C11 179.1(7) . . . . ?
C10 N2 C9 C8 171.4(7) . . . . ?
C10 C11 C12 N3 -67.7(9) . . . . ?
C12 N3 C13 C14 168.7(7) . . . . ?
C13 N3 C12 C11 -105.7(9) . . . . ?
C13 C14 C15 C16 178.4(7) . . . . ?
C13 C14 C19 O2 3.5(11) . . . . ?
C13 C14 C19 C18 -175.2(7) . . . . ?
C14 C15 C16 Cl4 176.0(6) . . . . ?
C14 C15 C16 C17 -4.2(12) . . . . ?
C15 C14 C19 O2 177.1(7) . . . . ?
C15 C14 C19 C18 -1.7(11) . . . . ?
C15 C16 C17 C18 0.8(12) . . . . ?
C16 C17 C18 Cl3 -179.3(6) . . . . ?
C16 C17 C18 C19 2.3(11) . . . . ?
C17 C18 C19 O2 179.4(7) . . . . ?
C17 C18 C19 C14 -1.8(10) . . . . ?
C19 C14 C15 C16 4.7(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_1d_LS
_database_code_depnum_ccdc_archive 'CCDC 2035918'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2020-10-07 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;
_audit_creation_date             2020-10-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 Cl4 Fe N4 O2 Se'
_chemical_formula_sum            'C20 H17 Cl4 Fe N4 O2 Se'
_chemical_formula_weight         621.99
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.3908(2)
_cell_length_b                   22.2708(6)
_cell_length_c                   12.6870(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.222(2)
_cell_angle_gamma                90
_cell_volume                     2307.97(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    36882
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      71.96
_cell_measurement_theta_min      3.97
_shelx_estimated_absorpt_T_max   0.655
_shelx_estimated_absorpt_T_min   0.338
_exptl_absorpt_coefficient_mu    11.537
_exptl_absorpt_correction_T_max  0.3597
_exptl_absorpt_correction_T_min  0.0746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1236
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0801
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            35730
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.596
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         5.349
_diffrn_ambient_temperature      100
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari with Xenocs Genix3D Cu HF'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3360
_reflns_number_total             4057
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction        
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.84, Darmstadt 2018
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.499
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.197
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4057
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0670
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1308P)²+4.7807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1716
_refine_ls_wR_factor_ref         0.1880
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C13(H13), C15(H15), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Se1 Se 0.47822(9) 0.69518(3) 0.40650(6) 0.0415(3) Uani 1 1 d . . . . .
Fe1 Fe 0.51222(10) 0.59134(4) 0.73910(7) 0.0236(3) Uani 1 1 d . . . . .
Cl1 Cl 0.00286(17) 0.57490(6) 0.49381(11) 0.0311(3) Uani 1 1 d . . . . .
Cl2 Cl -0.1482(2) 0.80153(7) 0.58137(15) 0.0467(4) Uani 1 1 d . . . . .
Cl3 Cl 0.25841(16) 0.55312(6) 1.01875(11) 0.0290(3) Uani 1 1 d . . . . .
Cl4 Cl 0.01117(18) 0.34826(7) 0.82232(13) 0.0383(4) Uani 1 1 d . . . . .
O1 O 0.2897(5) 0.59276(16) 0.6642(3) 0.0257(8) Uani 1 1 d . . . . .
O2 O 0.4599(4) 0.55373(16) 0.8604(3) 0.0255(8) Uani 1 1 d . . . . .
N1 N 0.5000(5) 0.6662(2) 0.8132(4) 0.0247(10) Uani 1 1 d . . . . .
N2 N 0.7488(6) 0.5921(2) 0.8177(4) 0.0274(10) Uani 1 1 d . . . . .
H2 H 0.758732 0.564219 0.880566 0.033 Uiso 1 1 calc R U . . .
N3 N 0.5402(6) 0.5121(2) 0.6774(4) 0.0267(10) Uani 1 1 d . . . . .
N4 N 0.5624(6) 0.6342(2) 0.6163(4) 0.0309(11) Uani 1 1 d . . . . .
C1 C 0.2008(7) 0.6414(2) 0.6487(4) 0.0255(12) Uani 1 1 d . . . . .
C2 C 0.0534(7) 0.6406(2) 0.5667(5) 0.0254(11) Uani 1 1 d . . . . .
C3 C -0.0534(7) 0.6887(3) 0.5463(5) 0.0296(12) Uani 1 1 d . . . . .
H3 H -0.151906 0.686063 0.491869 0.035 Uiso 1 1 calc R U . . .
C4 C -0.0142(8) 0.7409(3) 0.6067(5) 0.0326(13) Uani 1 1 d . . . . .
C5 C 0.1282(7) 0.7451(2) 0.6844(5) 0.0308(13) Uani 1 1 d . . . . .
H5 H 0.154205 0.781502 0.723593 0.037 Uiso 1 1 calc R U . . .
C6 C 0.2373(7) 0.6958(2) 0.7073(5) 0.0258(12) Uani 1 1 d . . . . .
C7 C 0.3824(7) 0.7040(2) 0.7919(5) 0.0269(12) Uani 1 1 d . . . . .
H7 H 0.391274 0.739473 0.834305 0.032 Uiso 1 1 calc R U . . .
C8 C 0.6427(7) 0.6763(3) 0.9024(5) 0.0311(13) Uani 1 1 d . . . . .
H8A H 0.630679 0.654165 0.967836 0.037 Uiso 1 1 calc R U . . .
H8B H 0.655076 0.719551 0.920063 0.037 Uiso 1 1 calc R U . . .
C9 C 0.7894(7) 0.6535(3) 0.8642(5) 0.0322(13) Uani 1 1 d . . . . .
H9A H 0.814519 0.680751 0.808572 0.039 Uiso 1 1 calc R U . . .
H9B H 0.886324 0.651633 0.925667 0.039 Uiso 1 1 calc R U . . .
C10 C 0.8706(7) 0.5719(3) 0.7572(5) 0.0313(13) Uani 1 1 d . . . . .
H10A H 0.980613 0.572344 0.806599 0.038 Uiso 1 1 calc R U . . .
H10B H 0.871903 0.600857 0.698110 0.038 Uiso 1 1 calc R U . . .
C11 C 0.8376(7) 0.5096(3) 0.7089(5) 0.0318(13) Uani 1 1 d . . . . .
H11A H 0.835722 0.480841 0.768030 0.038 Uiso 1 1 calc R U . . .
H11B H 0.929229 0.498149 0.675821 0.038 Uiso 1 1 calc R U . . .
C12 C 0.6784(7) 0.5039(3) 0.6239(5) 0.0296(12) Uani 1 1 d . . . . .
H12A H 0.673609 0.534731 0.567065 0.036 Uiso 1 1 calc R U . . .
H12B H 0.671700 0.463812 0.589457 0.036 Uiso 1 1 calc R U . . .
C13 C 0.4628(7) 0.4653(3) 0.6945(4) 0.0273(12) Uani 1 1 d . . . . .
H13 H 0.479334 0.429343 0.658143 0.033 Uiso 1 1 calc R U . . .
C14 C 0.3504(7) 0.4636(2) 0.7665(4) 0.0266(12) Uani 1 1 d . . . . .
C15 C 0.2481(7) 0.4129(2) 0.7608(5) 0.0271(12) Uani 1 1 d . . . . .
H15 H 0.248691 0.382519 0.708364 0.033 Uiso 1 1 calc R U . . .
C16 C 0.1471(7) 0.4080(2) 0.8320(5) 0.0275(12) Uani 1 1 d . . . . .
C17 C 0.1500(7) 0.4514(2) 0.9119(5) 0.0272(12) Uani 1 1 d . . . . .
H17 H 0.079374 0.448026 0.960459 0.033 Uiso 1 1 calc R U . . .
C18 C 0.2567(7) 0.4990(2) 0.9195(5) 0.0241(11) Uani 1 1 d . . . . .
C19 C 0.3592(6) 0.5076(2) 0.8469(4) 0.0240(11) Uani 1 1 d . . . . .
C20 C 0.5292(7) 0.6586(3) 0.5364(5) 0.0321(13) Uani 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
Se1 C20 1.800(6) . ?
Fe1 O1 1.892(4) . ?
Fe1 O2 1.890(4) . ?
Fe1 N1 1.927(4) . ?
Fe1 N2 2.008(5) . ?
Fe1 N3 1.966(5) . ?
Fe1 N4 1.954(5) . ?
Cl1 C2 1.731(6) . ?
Cl2 C4 1.740(6) . ?
Cl3 C18 1.740(5) . ?
Cl4 C16 1.739(5) . ?
O1 C1 1.304(7) . ?
O2 C19 1.315(7) . ?
N1 C7 1.278(8) . ?
N1 C8 1.465(7) . ?
N2 H2 1.0000 . ?
N2 C9 1.496(7) . ?
N2 C10 1.482(7) . ?
N3 C12 1.483(7) . ?
N3 C13 1.273(8) . ?
N4 C20 1.128(8) . ?
C1 C2 1.422(8) . ?
C1 C6 1.418(8) . ?
C2 C3 1.382(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(9) . ?
C4 C5 1.367(9) . ?
C5 H5 0.9500 . ?
C5 C6 1.417(8) . ?
C6 C7 1.439(8) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.510(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.516(9) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.518(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13 0.9500 . ?
C13 C14 1.456(8) . ?
C14 C15 1.409(8) . ?
C14 C19 1.405(8) . ?
C15 H15 0.9500 . ?
C15 C16 1.377(9) . ?
C16 C17 1.396(8) . ?
C17 H17 0.9500 . ?
C17 C18 1.378(8) . ?
C18 C19 1.410(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Fe1 N1 94.25(18) . . ?
O1 Fe1 N2 178.48(18) . . ?
O1 Fe1 N3 90.51(18) . . ?
O1 Fe1 N4 87.65(19) . . ?
O2 Fe1 O1 91.73(17) . . ?
O2 Fe1 N1 86.43(18) . . ?
O2 Fe1 N2 89.26(18) . . ?
O2 Fe1 N3 89.86(18) . . ?
O2 Fe1 N4 177.0(2) . . ?
N1 Fe1 N2 84.7(2) . . ?
N1 Fe1 N3 174.0(2) . . ?
N1 Fe1 N4 90.7(2) . . ?
N3 Fe1 N2 90.6(2) . . ?
N4 Fe1 N2 91.3(2) . . ?
N4 Fe1 N3 93.1(2) . . ?
C1 O1 Fe1 123.7(3) . . ?
C19 O2 Fe1 120.1(3) . . ?
C7 N1 Fe1 126.2(4) . . ?
C7 N1 C8 121.2(5) . . ?
C8 N1 Fe1 112.6(4) . . ?
Fe1 N2 H2 106.4 . . ?
C9 N2 Fe1 108.3(3) . . ?
C9 N2 H2 106.4 . . ?
C10 N2 Fe1 117.4(4) . . ?
C10 N2 H2 106.4 . . ?
C10 N2 C9 111.1(5) . . ?
C12 N3 Fe1 118.0(4) . . ?
C13 N3 Fe1 123.7(4) . . ?
C13 N3 C12 117.4(5) . . ?
C20 N4 Fe1 154.0(5) . . ?
O1 C1 C2 118.2(5) . . ?
O1 C1 C6 125.6(5) . . ?
C6 C1 C2 116.2(5) . . ?
C1 C2 Cl1 117.8(4) . . ?
C3 C2 Cl1 119.0(4) . . ?
C3 C2 C1 123.1(5) . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.9(6) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 Cl2 119.1(5) . . ?
C5 C4 Cl2 120.1(5) . . ?
C5 C4 C3 120.8(5) . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.7(5) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C7 123.0(5) . . ?
C5 C6 C1 120.2(5) . . ?
C5 C6 C7 116.8(5) . . ?
N1 C7 C6 123.7(5) . . ?
N1 C7 H7 118.2 . . ?
C6 C7 H7 118.2 . . ?
N1 C8 H8A 110.4 . . ?
N1 C8 H8B 110.4 . . ?
N1 C8 C9 106.5(5) . . ?
H8A C8 H8B 108.6 . . ?
C9 C8 H8A 110.4 . . ?
C9 C8 H8B 110.4 . . ?
N2 C9 C8 107.7(5) . . ?
N2 C9 H9A 110.2 . . ?
N2 C9 H9B 110.2 . . ?
C8 C9 H9A 110.2 . . ?
C8 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
N2 C10 H10A 108.8 . . ?
N2 C10 H10B 108.8 . . ?
N2 C10 C11 113.8(5) . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C10 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
C10 C11 C12 114.5(5) . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
N3 C12 C11 108.5(4) . . ?
N3 C12 H12A 110.0 . . ?
N3 C12 H12B 110.0 . . ?
C11 C12 H12A 110.0 . . ?
C11 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
N3 C13 H13 118.1 . . ?
N3 C13 C14 123.9(5) . . ?
C14 C13 H13 118.1 . . ?
C15 C14 C13 117.6(5) . . ?
C19 C14 C13 120.2(5) . . ?
C19 C14 C15 121.8(5) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.2(5) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 Cl4 120.4(5) . . ?
C15 C16 C17 120.7(5) . . ?
C17 C16 Cl4 118.8(4) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 C16 119.1(5) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 Cl3 118.8(4) . . ?
C17 C18 C19 122.9(5) . . ?
C19 C18 Cl3 118.2(4) . . ?
O2 C19 C14 124.4(5) . . ?
O2 C19 C18 119.4(5) . . ?
C14 C19 C18 116.1(5) . . ?
N4 C20 Se1 177.9(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 O1 C1 C2 162.2(4) . . . . ?
Fe1 O1 C1 C6 -18.1(7) . . . . ?
Fe1 O2 C19 C14 35.4(7) . . . . ?
Fe1 O2 C19 C18 -147.6(4) . . . . ?
Fe1 N1 C7 C6 0.3(8) . . . . ?
Fe1 N1 C8 C9 38.4(5) . . . . ?
Fe1 N2 C9 C8 37.3(5) . . . . ?
Fe1 N2 C10 C11 -55.2(6) . . . . ?
Fe1 N3 C12 C11 65.9(5) . . . . ?
Fe1 N3 C13 C14 -3.5(8) . . . . ?
Cl1 C2 C3 C4 178.5(4) . . . . ?
Cl2 C4 C5 C6 179.0(4) . . . . ?
Cl3 C18 C19 O2 4.4(7) . . . . ?
Cl3 C18 C19 C14 -178.4(4) . . . . ?
Cl4 C16 C17 C18 -179.6(4) . . . . ?
O1 Fe1 O2 C19 46.2(4) . . . . ?
O1 C1 C2 Cl1 0.2(7) . . . . ?
O1 C1 C2 C3 177.3(5) . . . . ?
O1 C1 C6 C5 -178.4(5) . . . . ?
O1 C1 C6 C7 1.0(9) . . . . ?
O2 Fe1 O1 C1 106.9(4) . . . . ?
N1 Fe1 O1 C1 20.4(4) . . . . ?
N1 Fe1 O2 C19 140.4(4) . . . . ?
N1 C8 C9 N2 -48.6(6) . . . . ?
N2 Fe1 O2 C19 -134.9(4) . . . . ?
N2 C10 C11 C12 63.4(7) . . . . ?
N3 Fe1 O1 C1 -163.2(4) . . . . ?
N3 Fe1 O2 C19 -44.3(4) . . . . ?
N3 C13 C14 C15 167.0(5) . . . . ?
N3 C13 C14 C19 -20.3(8) . . . . ?
N4 Fe1 O1 C1 -70.2(4) . . . . ?
C1 C2 C3 C4 1.4(8) . . . . ?
C1 C6 C7 N1 8.6(9) . . . . ?
C2 C1 C6 C5 1.3(8) . . . . ?
C2 C1 C6 C7 -179.3(5) . . . . ?
C2 C3 C4 Cl2 -180.0(4) . . . . ?
C2 C3 C4 C5 0.6(9) . . . . ?
C3 C4 C5 C6 -1.7(9) . . . . ?
C4 C5 C6 C1 0.7(9) . . . . ?
C4 C5 C6 C7 -178.8(5) . . . . ?
C5 C6 C7 N1 -171.9(5) . . . . ?
C6 C1 C2 Cl1 -179.5(4) . . . . ?
C6 C1 C2 C3 -2.3(8) . . . . ?
C7 N1 C8 C9 -142.8(5) . . . . ?
C8 N1 C7 C6 -178.3(5) . . . . ?
C9 N2 C10 C11 179.3(5) . . . . ?
C10 N2 C9 C8 167.7(5) . . . . ?
C10 C11 C12 N3 -66.8(6) . . . . ?
C12 N3 C13 C14 165.6(5) . . . . ?
C13 N3 C12 C11 -103.9(6) . . . . ?
C13 C14 C15 C16 176.2(5) . . . . ?
C13 C14 C19 O2 3.1(8) . . . . ?
C13 C14 C19 C18 -174.0(5) . . . . ?
C14 C15 C16 Cl4 176.5(4) . . . . ?
C14 C15 C16 C17 -2.5(8) . . . . ?
C15 C14 C19 O2 175.5(5) . . . . ?
C15 C14 C19 C18 -1.6(8) . . . . ?
C15 C16 C17 C18 -0.6(8) . . . . ?
C16 C17 C18 Cl3 179.5(4) . . . . ?
C16 C17 C18 C19 2.8(8) . . . . ?
C17 C18 C19 O2 -178.9(5) . . . . ?
C17 C18 C19 C14 -1.7(8) . . . . ?
C19 C14 C15 C16 3.6(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       'Magnetic properties'
