# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1895806'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2019-02-06 deposited with the CCDC.	2019-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 Cl4 Fe2 N3 O'
_chemical_formula_sum            'C17 H15 Cl4 Fe2 N3 O'
_chemical_formula_weight         530.82

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'
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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'


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

_cell_length_a                   7.7796(3)
_cell_length_b                   15.2532(6)
_cell_length_c                   17.3510(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.908(4)
_cell_angle_gamma                90
_cell_volume                     2054.15(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4800
_cell_measurement_theta_min      2.5494
_cell_measurement_theta_max      73.5668

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    16.225
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.36561
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.4 (release 09-12-2010 CrysAlis171 .NET)
(compiled Dec  9 2010,10:47:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Nova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            9063
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.862
_diffrn_reflns_theta_max         74.340
_diffrn_reflns_theta_full        70.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4080
_reflns_number_gt                3432
_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       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'

_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)+(0.0610P)²+0.9300P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4080
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1147
_refine_ls_wR_factor_gt          0.1066
_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 0.41649(7) 0.25406(3) 0.32673(3) 0.03786(15) Uani 1 1 d . . . . .
Cl1 Cl 0.13265(12) 0.24935(6) 0.32291(6) 0.0538(2) Uani 1 1 d . . . . .
N1 N 0.4637(4) 0.12442(17) 0.28018(15) 0.0416(6) Uani 1 1 d . . . . .
O1 O 0.5260(4) 0.23779(17) 0.41740(15) 0.0592(7) Uani 1 1 d . . . . .
C2 C 0.4265(5) 0.0483(2) 0.3133(2) 0.0465(8) Uani 1 1 d . . . . .
C21 C 0.3520(6) 0.0499(3) 0.3911(2) 0.0635(11) Uani 1 1 d . . . . .
H21A H 0.4377 0.0703 0.4294 0.095 Uiso 1 1 calc R U . . .
H21B H 0.3163 -0.0082 0.4043 0.095 Uiso 1 1 calc R U . . .
H21C H 0.2543 0.0885 0.3894 0.095 Uiso 1 1 calc R U . . .
C3 C 0.4569(5) -0.0307(2) 0.2767(2) 0.0552(9) Uani 1 1 d . . . . .
H3 H 0.4311 -0.0834 0.3003 0.066 Uiso 1 1 calc R U . . .
C4 C 0.5248(5) -0.0308(2) 0.2059(2) 0.0568(9) Uani 1 1 d . . . . .
H4 H 0.5440 -0.0834 0.1808 0.068 Uiso 1 1 calc R U . . .
C5 C 0.5641(5) 0.0476(2) 0.1724(2) 0.0529(8) Uani 1 1 d . . . . .
H5 H 0.6106 0.0486 0.1244 0.064 Uiso 1 1 calc R U . . .
C6 C 0.5338(4) 0.1245(2) 0.21051(19) 0.0418(7) Uani 1 1 d . . . . .
C7 C 0.5764(4) 0.2115(2) 0.18084(18) 0.0414(7) Uani 1 1 d . . . . .
N8 N 0.5348(3) 0.27857(17) 0.22524(15) 0.0384(6) Uani 1 1 d . . . . .
C9 C 0.5626(4) 0.3618(2) 0.20408(18) 0.0419(7) Uani 1 1 d . . . . .
C10 C 0.6359(5) 0.3797(3) 0.1353(2) 0.0551(9) Uani 1 1 d . . . . .
H10 H 0.6530 0.4373 0.1200 0.066 Uiso 1 1 calc R U . . .
C11 C 0.6829(5) 0.3108(3) 0.0900(2) 0.0601(10) Uani 1 1 d . . . . .
H11 H 0.7346 0.3217 0.0442 0.072 Uiso 1 1 calc R U . . .
C12 C 0.6538(5) 0.2263(3) 0.1124(2) 0.0551(9) Uani 1 1 d . . . . .
H12 H 0.6854 0.1795 0.0820 0.066 Uiso 1 1 calc R U . . .
C13 C 0.5077(4) 0.4285(2) 0.25866(18) 0.0408(7) Uani 1 1 d . . . . .
N14 N 0.4415(4) 0.39627(17) 0.32298(15) 0.0403(6) Uani 1 1 d . . . . .
C15 C 0.3909(4) 0.4513(2) 0.37742(19) 0.0450(7) Uani 1 1 d . . . . .
C151 C 0.3195(5) 0.4149(3) 0.4481(2) 0.0570(9) Uani 1 1 d . . . . .
H15A H 0.2172 0.3819 0.4339 0.085 Uiso 1 1 calc R U . . .
H15B H 0.2918 0.4621 0.4817 0.085 Uiso 1 1 calc R U . . .
H15C H 0.4034 0.3773 0.4743 0.085 Uiso 1 1 calc R U . . .
C16 C 0.4048(5) 0.5412(2) 0.3673(2) 0.0515(8) Uani 1 1 d . . . . .
H16 H 0.3692 0.5792 0.4050 0.062 Uiso 1 1 calc R U . . .
C17 C 0.4708(5) 0.5740(2) 0.3021(2) 0.0552(9) Uani 1 1 d . . . . .
H17 H 0.4795 0.6343 0.2952 0.066 Uiso 1 1 calc R U . . .
C18 C 0.5240(5) 0.5174(2) 0.2470(2) 0.0500(8) Uani 1 1 d . . . . .
H18 H 0.5703 0.5386 0.2027 0.060 Uiso 1 1 calc R U . . .
Fe2 Fe 0.71540(7) 0.23216(3) 0.47919(3) 0.04169(15) Uani 1 1 d . . . . .
Cl21 Cl 0.86091(14) 0.11214(6) 0.44989(6) 0.0663(3) Uani 1 1 d . . . . .
Cl22 Cl 0.85039(13) 0.36070(6) 0.46889(6) 0.0612(3) Uani 1 1 d . . . . .
Cl23 Cl 0.64651(13) 0.22165(6) 0.60096(4) 0.0536(2) 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 O1 1.755(2) . ?
Fe1 N8 2.076(3) . ?
Fe1 N1 2.177(3) . ?
Fe1 N14 2.179(3) . ?
Fe1 Cl1 2.2058(10) . ?
N1 C2 1.336(4) . ?
N1 C6 1.360(4) . ?
O1 Fe2 1.764(3) . ?
C2 C3 1.389(5) . ?
C2 C21 1.507(5) . ?
C3 C4 1.370(6) . ?
C4 C5 1.373(5) . ?
C5 C6 1.375(5) . ?
C6 C7 1.469(5) . ?
C7 N8 1.334(4) . ?
C7 C12 1.386(5) . ?
N8 C9 1.343(4) . ?
C9 C10 1.384(5) . ?
C9 C13 1.473(5) . ?
C10 C11 1.377(6) . ?
C11 C12 1.369(6) . ?
C13 N14 1.353(4) . ?
C13 C18 1.378(4) . ?
N14 C15 1.343(4) . ?
C15 C16 1.387(5) . ?
C15 C151 1.487(5) . ?
C16 C17 1.369(5) . ?
C17 C18 1.374(5) . ?
Fe2 Cl23 2.2207(9) . ?
Fe2 Cl21 2.2293(10) . ?
Fe2 Cl22 2.2371(10) . ?

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 N8 124.74(14) . . ?
O1 Fe1 N1 96.91(11) . . ?
N8 Fe1 N1 75.71(10) . . ?
O1 Fe1 N14 97.39(11) . . ?
N8 Fe1 N14 75.51(10) . . ?
N1 Fe1 N14 151.11(10) . . ?
O1 Fe1 Cl1 116.50(12) . . ?
N8 Fe1 Cl1 118.76(8) . . ?
N1 Fe1 Cl1 98.81(8) . . ?
N14 Fe1 Cl1 97.05(8) . . ?
C2 N1 C6 119.7(3) . . ?
C2 N1 Fe1 125.7(2) . . ?
C6 N1 Fe1 114.6(2) . . ?
Fe1 O1 Fe2 152.4(2) . . ?
N1 C2 C3 120.6(3) . . ?
N1 C2 C21 118.7(3) . . ?
C3 C2 C21 120.8(3) . . ?
C4 C3 C2 119.9(4) . . ?
C3 C4 C5 119.3(3) . . ?
C4 C5 C6 119.3(3) . . ?
N1 C6 C5 121.3(3) . . ?
N1 C6 C7 115.2(3) . . ?
C5 C6 C7 123.5(3) . . ?
N8 C7 C12 120.4(3) . . ?
N8 C7 C6 114.9(3) . . ?
C12 C7 C6 124.7(3) . . ?
C7 N8 C9 121.2(3) . . ?
C7 N8 Fe1 119.4(2) . . ?
C9 N8 Fe1 119.4(2) . . ?
N8 C9 C10 120.4(3) . . ?
N8 C9 C13 114.7(3) . . ?
C10 C9 C13 124.9(3) . . ?
C11 C10 C9 118.8(4) . . ?
C12 C11 C10 120.1(3) . . ?
C11 C12 C7 119.1(4) . . ?
N14 C13 C18 121.5(3) . . ?
N14 C13 C9 115.0(3) . . ?
C18 C13 C9 123.5(3) . . ?
C15 N14 C13 120.0(3) . . ?
C15 N14 Fe1 124.8(2) . . ?
C13 N14 Fe1 115.2(2) . . ?
N14 C15 C16 120.0(3) . . ?
N14 C15 C151 119.4(3) . . ?
C16 C15 C151 120.6(3) . . ?
C17 C16 C15 120.2(3) . . ?
C16 C17 C18 119.5(3) . . ?
C17 C18 C13 118.8(3) . . ?
O1 Fe2 Cl23 109.63(11) . . ?
O1 Fe2 Cl21 108.51(10) . . ?
Cl23 Fe2 Cl21 108.48(4) . . ?
O1 Fe2 Cl22 106.61(10) . . ?
Cl23 Fe2 Cl22 106.52(4) . . ?
Cl21 Fe2 Cl22 116.94(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
N8 Fe1 O1 Fe2 2.6(4) . . . . ?
N1 Fe1 O1 Fe2 79.9(4) . . . . ?
N14 Fe1 O1 Fe2 -74.9(4) . . . . ?
Cl1 Fe1 O1 Fe2 -176.6(3) . . . . ?
C6 N1 C2 C3 -0.8(5) . . . . ?
Fe1 N1 C2 C3 177.6(3) . . . . ?
C6 N1 C2 C21 178.9(3) . . . . ?
Fe1 N1 C2 C21 -2.7(5) . . . . ?
N1 C2 C3 C4 -0.3(6) . . . . ?
C21 C2 C3 C4 180.0(4) . . . . ?
C2 C3 C4 C5 0.8(6) . . . . ?
C3 C4 C5 C6 -0.2(6) . . . . ?
C2 N1 C6 C5 1.4(5) . . . . ?
Fe1 N1 C6 C5 -177.2(3) . . . . ?
C2 N1 C6 C7 -177.5(3) . . . . ?
Fe1 N1 C6 C7 3.9(4) . . . . ?
C4 C5 C6 N1 -0.9(5) . . . . ?
C4 C5 C6 C7 178.0(3) . . . . ?
N1 C6 C7 N8 -2.2(4) . . . . ?
C5 C6 C7 N8 178.9(3) . . . . ?
N1 C6 C7 C12 177.8(3) . . . . ?
C5 C6 C7 C12 -1.1(6) . . . . ?
C12 C7 N8 C9 1.6(5) . . . . ?
C6 C7 N8 C9 -178.3(3) . . . . ?
C12 C7 N8 Fe1 179.3(3) . . . . ?
C6 C7 N8 Fe1 -0.7(4) . . . . ?
C7 N8 C9 C10 -0.1(5) . . . . ?
Fe1 N8 C9 C10 -177.8(3) . . . . ?
C7 N8 C9 C13 179.2(3) . . . . ?
Fe1 N8 C9 C13 1.6(4) . . . . ?
N8 C9 C10 C11 -1.4(6) . . . . ?
C13 C9 C10 C11 179.3(4) . . . . ?
C9 C10 C11 C12 1.4(6) . . . . ?
C10 C11 C12 C7 0.1(6) . . . . ?
N8 C7 C12 C11 -1.6(6) . . . . ?
C6 C7 C12 C11 178.4(4) . . . . ?
N8 C9 C13 N14 1.6(4) . . . . ?
C10 C9 C13 N14 -179.0(3) . . . . ?
N8 C9 C13 C18 -179.5(3) . . . . ?
C10 C9 C13 C18 -0.2(5) . . . . ?
C18 C13 N14 C15 -0.3(5) . . . . ?
C9 C13 N14 C15 178.6(3) . . . . ?
C18 C13 N14 Fe1 177.2(3) . . . . ?
C9 C13 N14 Fe1 -3.9(3) . . . . ?
C13 N14 C15 C16 0.7(5) . . . . ?
Fe1 N14 C15 C16 -176.7(3) . . . . ?
C13 N14 C15 C151 -179.6(3) . . . . ?
Fe1 N14 C15 C151 3.1(5) . . . . ?
N14 C15 C16 C17 -0.3(5) . . . . ?
C151 C15 C16 C17 179.9(4) . . . . ?
C15 C16 C17 C18 -0.4(6) . . . . ?
C16 C17 C18 C13 0.7(6) . . . . ?
N14 C13 C18 C17 -0.3(5) . . . . ?
C9 C13 C18 C17 -179.1(3) . . . . ?
Fe1 O1 Fe2 Cl23 171.2(3) . . . . ?
Fe1 O1 Fe2 Cl21 -70.5(4) . . . . ?
Fe1 O1 Fe2 Cl22 56.2(4) . . . . ?


_refine_diff_density_max         0.581
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.068

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1895807'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2019-02-06 deposited with the CCDC.	2019-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C17 H15 Cl2 Fe N3), 2(Cl4 Fe), C7 H8'
_chemical_formula_sum            'C41 H38 Cl12 Fe4 N6'
_chemical_formula_weight         1263.57

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.31307(9)
_cell_length_b                   31.0196(3)
_cell_length_c                   9.76421(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.5938(10)
_cell_angle_gamma                90
_cell_volume                     2501.22(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(1)
_cell_measurement_reflns_used    13269
_cell_measurement_theta_min      2.8360
_cell_measurement_theta_max      75.7090

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_F_000             1268
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_rad          0.12
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    15.323
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.05176
_exptl_absorpt_correction_T_max  0.15168
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Spherical absorption correction
 using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      130(1)
__diffrn_ambient_environment     N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.5357
_diffrn_reflns_number            23499
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_av_R_equivalents  0.1200
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.849
_diffrn_reflns_theta_max         76.169
_diffrn_reflns_theta_full        67.500
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5159
_reflns_number_gt                4406
_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       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'

_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)+(0.0980P)²+15.2744P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5159
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0854
_refine_ls_wR_factor_ref         0.2202
_refine_ls_wR_factor_gt          0.2105
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.67014(10) 0.60401(3) 0.53314(9) 0.0328(3) Uani 1 1 d . . . . .
Cl1 Cl 0.7445(2) 0.57041(6) 0.35372(17) 0.0472(4) Uani 1 1 d . . . . .
Cl2 Cl 0.59132(19) 0.56907(5) 0.70746(18) 0.0468(4) Uani 1 1 d . . . . .
N1 N 0.4317(6) 0.62306(17) 0.4409(5) 0.0370(11) Uani 1 1 d . . . . .
C2 C 0.3130(8) 0.5959(2) 0.3905(7) 0.0452(15) Uani 1 1 d . . . . .
C21 C 0.3417(10) 0.5486(3) 0.3920(10) 0.059(2) Uani 1 1 d . . . . .
H21A H 0.4382 0.5422 0.3467 0.089 Uiso 1 1 calc R U . . .
H21B H 0.2477 0.5340 0.3429 0.089 Uiso 1 1 calc R U . . .
H21C H 0.3582 0.5384 0.4876 0.089 Uiso 1 1 calc R U . . .
C3 C 0.1615(8) 0.6125(3) 0.3358(7) 0.0520(18) Uani 1 1 d . . . . .
H3 H 0.0772 0.5933 0.3010 0.062 Uiso 1 1 calc R U . . .
C4 C 0.1354(9) 0.6557(3) 0.3325(8) 0.057(2) Uani 1 1 d . . . . .
H4 H 0.0334 0.6669 0.2951 0.069 Uiso 1 1 calc R U . . .
C5 C 0.2580(9) 0.6832(3) 0.3839(7) 0.0500(17) Uani 1 1 d . . . . .
H5 H 0.2417 0.7135 0.3821 0.060 Uiso 1 1 calc R U . . .
C6 C 0.4049(8) 0.6660(2) 0.4382(6) 0.0372(13) Uani 1 1 d . . . . .
C7 C 0.5427(8) 0.6928(2) 0.4950(6) 0.0385(13) Uani 1 1 d . . . . .
N8 N 0.6749(5) 0.67007(17) 0.5411(5) 0.0335(11) Uani 1 1 d . . . . .
C9 C 0.8127(8) 0.6898(2) 0.5928(6) 0.0378(13) Uani 1 1 d . . . . .
C10 C 0.8204(9) 0.7347(2) 0.5969(7) 0.0455(15) Uani 1 1 d . . . . .
H10 H 0.9183 0.7489 0.6306 0.055 Uiso 1 1 calc R U . . .
C11 C 0.6851(10) 0.7579(2) 0.5517(7) 0.0508(17) Uani 1 1 d . . . . .
H11 H 0.6882 0.7885 0.5558 0.061 Uiso 1 1 calc R U . . .
C12 C 0.5441(9) 0.7373(2) 0.5004(7) 0.0435(15) Uani 1 1 d . . . . .
H12 H 0.4497 0.7534 0.4694 0.052 Uiso 1 1 calc R U . . .
C13 C 0.9471(8) 0.6608(2) 0.6400(6) 0.0371(13) Uani 1 1 d . . . . .
N14 N 0.9116(6) 0.61830(17) 0.6279(5) 0.0354(11) Uani 1 1 d . . . . .
C15 C 1.0244(8) 0.5886(2) 0.6714(7) 0.0406(14) Uani 1 1 d . . . . .
C151 C 0.9853(8) 0.5417(2) 0.6597(8) 0.0455(15) Uani 1 1 d . . . . .
H15A H 0.9164 0.5336 0.7305 0.068 Uiso 1 1 calc R U . . .
H15B H 1.0858 0.5249 0.6726 0.068 Uiso 1 1 calc R U . . .
H15C H 0.9282 0.5357 0.5682 0.068 Uiso 1 1 calc R U . . .
C16 C 1.1803(8) 0.6020(3) 0.7298(7) 0.0487(17) Uani 1 1 d . . . . .
H16 H 1.2594 0.5812 0.7623 0.058 Uiso 1 1 calc R U . . .
C17 C 1.2162(8) 0.6447(3) 0.7392(7) 0.0508(17) Uani 1 1 d . . . . .
H17 H 1.3214 0.6539 0.7760 0.061 Uiso 1 1 calc R U . . .
C18 C 1.0998(9) 0.6746(2) 0.6952(7) 0.0477(16) Uani 1 1 d . . . . .
H18 H 1.1236 0.7045 0.7026 0.057 Uiso 1 1 calc R U . . .
Fe1A Fe 0.66342(11) 0.67035(3) 0.03104(9) 0.0348(3) Uani 1 1 d . . . . .
Cl1A Cl 0.4795(3) 0.62316(7) 0.0670(2) 0.0630(5) Uani 1 1 d . . . . .
Cl2A Cl 0.8936(2) 0.64554(6) -0.02302(18) 0.0508(4) Uani 1 1 d . . . . .
Cl3A Cl 0.5598(2) 0.71337(5) -0.13624(16) 0.0442(4) Uani 1 1 d . . . . .
Cl4A Cl 0.7289(2) 0.71011(5) 0.21634(16) 0.0450(4) Uani 1 1 d . . . . .
C1B C 0.8356(13) 0.4948(3) 1.0036(9) 0.069(2) Uani 1 1 d . . . . .
H1B H 0.7223 0.4916 1.0060 0.083 Uiso 0.5 1 calc R U P A 1
C11B C 0.670(2) 0.4918(6) 1.012(2) 0.071(5) Uani 0.5 1 d . . P B 2
H11A H 0.6513 0.4792 1.1006 0.106 Uiso 0.5 1 calc R U P B 2
H11B H 0.6199 0.4735 0.9368 0.106 Uiso 0.5 1 calc R U P B 2
H11C H 0.6216 0.5206 1.0032 0.106 Uiso 0.5 1 calc R U P B 2
C2B C 0.9085(14) 0.5346(3) 1.0315(9) 0.071(3) Uani 1 1 d . . . . .
H2B H 0.8446 0.5584 1.0536 0.085 Uiso 1 1 calc R U . . .
C3B C 1.0732(14) 0.5399(3) 1.0274(9) 0.072(3) Uani 1 1 d . . . . .
H3B H 1.1223 0.5673 1.0459 0.086 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 N8 2.051(5) . ?
Fe1 N14 2.157(5) . ?
Fe1 N1 2.163(5) . ?
Fe1 Cl2 2.1811(18) . ?
Fe1 Cl1 2.1878(18) . ?
N1 C2 1.347(9) . ?
N1 C6 1.350(8) . ?
C2 C3 1.407(10) . ?
C2 C21 1.487(11) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C3 C4 1.359(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.471(9) . ?
C7 N8 1.339(8) . ?
C7 C12 1.383(9) . ?
N8 C9 1.345(8) . ?
C9 C10 1.393(9) . ?
C9 C13 1.467(9) . ?
C10 C11 1.367(11) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(11) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 N14 1.354(8) . ?
C13 C18 1.388(9) . ?
N14 C15 1.347(8) . ?
C15 C16 1.417(9) . ?
C15 C151 1.493(9) . ?
C151 H15A 0.9800 . ?
C151 H15B 0.9800 . ?
C151 H15C 0.9800 . ?
C16 C17 1.360(11) . ?
C16 H16 0.9500 . ?
C17 C18 1.372(11) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
Fe1A Cl1A 2.174(2) . ?
Fe1A Cl2A 2.1828(19) . ?
Fe1A Cl4A 2.2056(18) . ?
Fe1A Cl3A 2.2064(18) . ?
C1B C3B 1.370(13) 3_767 ?
C1B C2B 1.389(14) . ?
C1B C11B 1.39(2) . ?
C1B H1B 0.9500 . ?
C11B H11A 0.9800 . ?
C11B H11B 0.9800 . ?
C11B H11C 0.9800 . ?
C2B C3B 1.384(15) . ?
C2B H2B 0.9500 . ?
C3B C1B 1.370(13) 3_767 ?
C3B H3B 0.9500 . ?

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
N8 Fe1 N14 76.44(19) . . ?
N8 Fe1 N1 75.9(2) . . ?
N14 Fe1 N1 152.3(2) . . ?
N8 Fe1 Cl2 118.24(15) . . ?
N14 Fe1 Cl2 96.63(15) . . ?
N1 Fe1 Cl2 96.75(15) . . ?
N8 Fe1 Cl1 120.02(15) . . ?
N14 Fe1 Cl1 96.12(14) . . ?
N1 Fe1 Cl1 97.26(15) . . ?
Cl2 Fe1 Cl1 121.74(8) . . ?
C2 N1 C6 119.8(6) . . ?
C2 N1 Fe1 125.4(5) . . ?
C6 N1 Fe1 114.8(4) . . ?
N1 C2 C3 119.8(7) . . ?
N1 C2 C21 120.2(6) . . ?
C3 C2 C21 120.0(7) . . ?
C2 C21 H21A 109.5 . . ?
C2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C4 C3 C2 120.2(7) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.5(7) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 118.9(7) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
N1 C6 C5 121.7(7) . . ?
N1 C6 C7 115.5(5) . . ?
C5 C6 C7 122.8(6) . . ?
N8 C7 C12 120.6(6) . . ?
N8 C7 C6 113.8(6) . . ?
C12 C7 C6 125.6(6) . . ?
C7 N8 C9 121.1(6) . . ?
C7 N8 Fe1 120.1(4) . . ?
C9 N8 Fe1 118.8(4) . . ?
N8 C9 C10 120.0(6) . . ?
N8 C9 C13 115.1(5) . . ?
C10 C9 C13 124.9(6) . . ?
C11 C10 C9 119.0(7) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 120.4(6) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 118.7(6) . . ?
C11 C12 H12 120.6 . . ?
C7 C12 H12 120.6 . . ?
N14 C13 C18 120.9(6) . . ?
N14 C13 C9 114.8(5) . . ?
C18 C13 C9 124.3(6) . . ?
C15 N14 C13 120.1(5) . . ?
C15 N14 Fe1 125.0(4) . . ?
C13 N14 Fe1 114.9(4) . . ?
N14 C15 C16 119.9(6) . . ?
N14 C15 C151 120.3(6) . . ?
C16 C15 C151 119.8(6) . . ?
C15 C151 H15A 109.5 . . ?
C15 C151 H15B 109.5 . . ?
H15A C151 H15B 109.5 . . ?
C15 C151 H15C 109.5 . . ?
H15A C151 H15C 109.5 . . ?
H15B C151 H15C 109.5 . . ?
C17 C16 C15 119.8(7) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 119.7(6) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C13 119.6(7) . . ?
C17 C18 H18 120.2 . . ?
C13 C18 H18 120.2 . . ?
Cl1A Fe1A Cl2A 117.01(9) . . ?
Cl1A Fe1A Cl4A 110.83(9) . . ?
Cl2A Fe1A Cl4A 104.77(7) . . ?
Cl1A Fe1A Cl3A 107.75(8) . . ?
Cl2A Fe1A Cl3A 108.23(8) . . ?
Cl4A Fe1A Cl3A 107.91(7) . . ?
C3B C1B C2B 120.1(10) 3_767 . ?
C3B C1B C11B 122.5(13) 3_767 . ?
C2B C1B C11B 117.4(12) . . ?
C3B C1B H1B 120.0 3_767 . ?
C2B C1B H1B 120.0 . . ?
C1B C11B H11A 109.5 . . ?
C1B C11B H11B 109.5 . . ?
H11A C11B H11B 109.5 . . ?
C1B C11B H11C 109.5 . . ?
H11A C11B H11C 109.5 . . ?
H11B C11B H11C 109.5 . . ?
C3B C2B C1B 120.8(9) . . ?
C3B C2B H2B 119.6 . . ?
C1B C2B H2B 119.6 . . ?
C1B C3B C2B 119.1(10) 3_767 . ?
C1B C3B H3B 120.5 3_767 . ?
C2B C3B H3B 120.5 . . ?

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
C6 N1 C2 C3 -0.3(10) . . . . ?
Fe1 N1 C2 C3 178.6(5) . . . . ?
C6 N1 C2 C21 179.5(7) . . . . ?
Fe1 N1 C2 C21 -1.7(9) . . . . ?
N1 C2 C3 C4 0.6(11) . . . . ?
C21 C2 C3 C4 -179.1(7) . . . . ?
C2 C3 C4 C5 -0.4(11) . . . . ?
C3 C4 C5 C6 -0.2(11) . . . . ?
C2 N1 C6 C5 -0.4(9) . . . . ?
Fe1 N1 C6 C5 -179.3(5) . . . . ?
C2 N1 C6 C7 -179.6(6) . . . . ?
Fe1 N1 C6 C7 1.4(7) . . . . ?
C4 C5 C6 N1 0.6(10) . . . . ?
C4 C5 C6 C7 179.8(6) . . . . ?
N1 C6 C7 N8 0.0(8) . . . . ?
C5 C6 C7 N8 -179.3(6) . . . . ?
N1 C6 C7 C12 178.7(6) . . . . ?
C5 C6 C7 C12 -0.6(10) . . . . ?
C12 C7 N8 C9 -0.6(9) . . . . ?
C6 C7 N8 C9 178.2(5) . . . . ?
C12 C7 N8 Fe1 179.7(4) . . . . ?
C6 C7 N8 Fe1 -1.6(7) . . . . ?
C7 N8 C9 C10 -1.0(9) . . . . ?
Fe1 N8 C9 C10 178.7(5) . . . . ?
C7 N8 C9 C13 179.7(5) . . . . ?
Fe1 N8 C9 C13 -0.6(7) . . . . ?
N8 C9 C10 C11 2.0(9) . . . . ?
C13 C9 C10 C11 -178.9(6) . . . . ?
C9 C10 C11 C12 -1.3(10) . . . . ?
C10 C11 C12 C7 -0.3(10) . . . . ?
N8 C7 C12 C11 1.3(9) . . . . ?
C6 C7 C12 C11 -177.4(6) . . . . ?
N8 C9 C13 N14 -1.6(8) . . . . ?
C10 C9 C13 N14 179.2(6) . . . . ?
N8 C9 C13 C18 179.3(6) . . . . ?
C10 C9 C13 C18 0.1(10) . . . . ?
C18 C13 N14 C15 0.9(9) . . . . ?
C9 C13 N14 C15 -178.2(5) . . . . ?
C18 C13 N14 Fe1 -178.0(5) . . . . ?
C9 C13 N14 Fe1 2.9(7) . . . . ?
C13 N14 C15 C16 0.0(9) . . . . ?
Fe1 N14 C15 C16 178.8(5) . . . . ?
C13 N14 C15 C151 179.3(6) . . . . ?
Fe1 N14 C15 C151 -1.9(9) . . . . ?
N14 C15 C16 C17 -1.3(10) . . . . ?
C151 C15 C16 C17 179.4(7) . . . . ?
C15 C16 C17 C18 1.7(11) . . . . ?
C16 C17 C18 C13 -0.8(11) . . . . ?
N14 C13 C18 C17 -0.5(10) . . . . ?
C9 C13 C18 C17 178.6(6) . . . . ?
C3B C1B C2B C3B 0.5(15) 3_767 . . . ?
C11B C1B C2B C3B 179.1(12) . . . . ?
C1B C2B C3B C1B -0.5(15) . . . 3_767 ?

_refine_diff_density_max         1.834
_refine_diff_density_min         -1.000
_refine_diff_density_rms         0.176

