# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2036444'
loop_
_audit_author_name
_audit_author_address
'Shouvik Chattopadhyay'
;Jadavpur University, kolkata
India
;
_audit_update_record             
;
2020-10-10 deposited with the CCDC.	2021-01-26 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         ?
_chemical_formula_sum            'C20 H20 Cl3 Fe N4 O2'
_chemical_formula_weight         510.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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                   13.642(2)
_cell_length_b                   12.843(2)
_cell_length_c                   13.658(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.055(5)
_cell_angle_gamma                90
_cell_volume                     2287.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    900
_cell_measurement_theta_min      2.696
_cell_measurement_theta_max      27.534

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            GREEN
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_F_000             1044
_exptl_transmission_factor_min   0.534
_exptl_transmission_factor_max   0.743
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    1.033
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8 QUEST AREA DETECTOR'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            76272
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.969
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_full        25.242
_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             5222
_reflns_number_gt                4818
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0808P)²+1.1094P] 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         5222
_refine_ls_number_parameters     264
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1390
_refine_ls_wR_factor_gt          0.1266
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 0.80176(2) 0.52944(2) 0.40846(2) 0.04242(13) Uani 1 1 d . . . . .
C1 C 0.60292(16) 0.64351(17) 0.32336(16) 0.0429(4) Uani 1 1 d . . . . .
C2 C 0.53817(18) 0.6942(2) 0.23764(17) 0.0520(5) Uani 1 1 d . . . . .
H2 H 0.554969 0.693930 0.176391 0.062 Uiso 1 1 calc R U . . .
C3 C 0.45013(18) 0.7446(2) 0.24201(19) 0.0543(5) Uani 1 1 d . . . . .
H3 H 0.407850 0.776783 0.183918 0.065 Uiso 1 1 calc R U . . .
C4 C 0.42505(18) 0.74701(19) 0.33269(19) 0.0515(5) Uani 1 1 d . . . . .
C5 C 0.48519(18) 0.69783(19) 0.41837(18) 0.0498(5) Uani 1 1 d . . . . .
H5 H 0.467301 0.699918 0.479015 0.060 Uiso 1 1 calc R U . . .
C6 C 0.57375(16) 0.64431(18) 0.41467(16) 0.0430(4) Uani 1 1 d . . . . .
C7 C 0.62952(17) 0.58869(19) 0.50554(16) 0.0468(5) Uani 1 1 d . . . . .
H7 H 0.605485 0.593810 0.562425 0.056 Uiso 1 1 calc R U . . .
C8 C 0.7495(2) 0.4761(2) 0.61231(18) 0.0551(6) Uani 1 1 d . . . . .
H8A H 0.712486 0.411172 0.609779 0.066 Uiso 1 1 calc R U . . .
H8B H 0.740091 0.517695 0.668171 0.066 Uiso 1 1 calc R U . . .
C9 C 0.86235(19) 0.4543(2) 0.62973(19) 0.0568(6) Uani 1 1 d . . . . .
H9A H 0.901710 0.517345 0.652056 0.068 Uiso 1 1 calc R U . . .
H9B H 0.885515 0.402081 0.682805 0.068 Uiso 1 1 calc R U . . .
C10 C 0.8429(2) 0.3087(2) 0.5060(2) 0.0616(6) Uani 1 1 d . . . . .
H10A H 0.831701 0.274317 0.565031 0.074 Uiso 1 1 calc R U . . .
H10B H 0.895489 0.270552 0.486326 0.074 Uiso 1 1 calc R U . . .
C11 C 0.7438(2) 0.3075(2) 0.4179(2) 0.0621(6) Uani 1 1 d . . . . .
H11A H 0.730735 0.238368 0.388233 0.075 Uiso 1 1 calc R U . . .
H11B H 0.686227 0.328176 0.441464 0.075 Uiso 1 1 calc R U . . .
C12 C 0.76010(19) 0.3515(2) 0.2542(2) 0.0554(5) Uani 1 1 d . . . . .
H12 H 0.735054 0.285350 0.232709 0.067 Uiso 1 1 calc R U . . .
C13 C 0.79751(18) 0.41411(19) 0.18477(19) 0.0510(5) Uani 1 1 d . . . . .
C14 C 0.7818(2) 0.3786(2) 0.0844(2) 0.0641(7) Uani 1 1 d . . . . .
H14 H 0.741164 0.320229 0.061377 0.077 Uiso 1 1 calc R U . . .
C15 C 0.8260(3) 0.4295(3) 0.0202(2) 0.0698(7) Uani 1 1 d . . . . .
C16 C 0.8882(2) 0.5156(2) 0.0529(2) 0.0619(6) Uani 1 1 d . . . . .
H16 H 0.918135 0.549154 0.008510 0.074 Uiso 1 1 calc R U . . .
C17 C 0.90532(18) 0.5510(2) 0.15149(19) 0.0525(5) Uani 1 1 d . . . . .
H17 H 0.946851 0.609052 0.173054 0.063 Uiso 1 1 calc R U . . .
C18 C 0.86155(16) 0.50167(19) 0.22052(17) 0.0455(4) Uani 1 1 d . . . . .
C19 C 0.4813(5) 0.3875(7) 0.2209(5) 0.1490(13) Uani 1 1 d . . . . .
C20 C 0.4927(5) 0.4358(6) 0.1298(5) 0.1490(13) Uani 1 1 d . . . . .
H20A H 0.550757 0.481754 0.147794 0.224 Uiso 1 1 calc R U . . .
H20B H 0.431965 0.474788 0.096752 0.224 Uiso 1 1 calc R U . . .
H20C H 0.503036 0.383080 0.083933 0.224 Uiso 1 1 calc R U . . .
Cl1 Cl 0.31276(6) 0.81063(7) 0.33507(6) 0.0760(2) Uani 1 1 d . . . . .
Cl2 Cl 0.80801(11) 0.38179(11) -0.10365(7) 0.1160(4) Uani 1 1 d . . . . .
Cl3 Cl 0.90164(5) 0.66744(5) 0.49634(5) 0.05737(17) Uani 1 1 d . . . . .
O1 O 0.68654(12) 0.59842(14) 0.31545(12) 0.0514(4) Uani 1 1 d . . . . .
O2 O 0.88431(13) 0.53590(13) 0.31501(13) 0.0496(4) Uani 1 1 d . . . . .
N1 N 0.70945(14) 0.53276(15) 0.51455(14) 0.0448(4) Uani 1 1 d . . . . .
N2 N 0.87846(15) 0.41698(17) 0.53397(17) 0.0534(5) Uani 1 1 d D . . . .
N3 N 0.75932(15) 0.38136(16) 0.34334(16) 0.0519(4) Uani 1 1 d . . . . .
N4 N 0.4809(4) 0.3467(5) 0.2915(4) 0.1490(13) Uani 1 1 d . . . . .
H2A H 0.9425(15) 0.417(3) 0.540(3) 0.073(9) Uiso 1 1 d 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 1.9232(16) . ?
Fe1 O2 1.9358(16) . ?
Fe1 N3 2.107(2) . ?
Fe1 N1 2.1812(19) . ?
Fe1 N2 2.251(2) . ?
Fe1 Cl3 2.3407(7) . ?
C1 O1 1.312(3) . ?
C1 C2 1.403(3) . ?
C1 C6 1.416(3) . ?
C2 C3 1.381(3) . ?
C3 C4 1.379(3) . ?
C4 C5 1.371(3) . ?
C4 Cl1 1.745(2) . ?
C5 C6 1.404(3) . ?
C6 C7 1.441(3) . ?
C7 N1 1.281(3) . ?
C8 N1 1.477(3) . ?
C8 C9 1.514(3) . ?
C9 N2 1.469(3) . ?
C10 N2 1.485(3) . ?
C10 C11 1.523(4) . ?
C11 N3 1.452(3) . ?
C12 N3 1.280(3) . ?
C12 C13 1.446(4) . ?
C13 C14 1.400(4) . ?
C13 C18 1.420(3) . ?
C14 C15 1.368(4) . ?
C15 C16 1.386(5) . ?
C15 Cl2 1.747(3) . ?
C16 C17 1.375(4) . ?
C17 C18 1.406(3) . ?
C18 O2 1.312(3) . ?
C19 N4 1.099(8) . ?
C19 C20 1.440(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 O2 93.76(7) . . ?
O1 Fe1 N3 93.83(8) . . ?
O2 Fe1 N3 84.34(7) . . ?
O1 Fe1 N1 84.87(7) . . ?
O2 Fe1 N1 176.41(7) . . ?
N3 Fe1 N1 99.05(7) . . ?
O1 Fe1 N2 154.95(7) . . ?
O2 Fe1 N2 107.41(8) . . ?
N3 Fe1 N2 75.59(8) . . ?
N1 Fe1 N2 74.73(7) . . ?
O1 Fe1 Cl3 103.29(6) . . ?
O2 Fe1 Cl3 86.67(5) . . ?
N3 Fe1 Cl3 161.14(6) . . ?
N1 Fe1 Cl3 90.42(5) . . ?
N2 Fe1 Cl3 91.42(6) . . ?
O1 C1 C2 119.08(19) . . ?
O1 C1 C6 123.48(19) . . ?
C2 C1 C6 117.4(2) . . ?
C3 C2 C1 121.6(2) . . ?
C4 C3 C2 119.8(2) . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 Cl1 120.59(19) . . ?
C3 C4 Cl1 118.55(18) . . ?
C4 C5 C6 120.1(2) . . ?
C5 C6 C1 120.16(19) . . ?
C5 C6 C7 117.03(19) . . ?
C1 C6 C7 122.78(19) . . ?
N1 C7 C6 125.5(2) . . ?
N1 C8 C9 108.8(2) . . ?
N2 C9 C8 109.4(2) . . ?
N2 C10 C11 111.1(2) . . ?
N3 C11 C10 105.6(2) . . ?
N3 C12 C13 124.1(2) . . ?
C14 C13 C18 119.8(2) . . ?
C14 C13 C12 118.6(2) . . ?
C18 C13 C12 121.0(2) . . ?
C15 C14 C13 120.1(3) . . ?
C14 C15 C16 121.2(3) . . ?
C14 C15 Cl2 119.3(2) . . ?
C16 C15 Cl2 119.4(2) . . ?
C17 C16 C15 119.5(3) . . ?
C16 C17 C18 121.6(2) . . ?
O2 C18 C17 119.0(2) . . ?
O2 C18 C13 123.2(2) . . ?
C17 C18 C13 117.8(2) . . ?
N4 C19 C20 173.7(9) . . ?
C1 O1 Fe1 135.32(13) . . ?
C18 O2 Fe1 128.24(15) . . ?
C7 N1 C8 116.18(19) . . ?
C7 N1 Fe1 126.03(15) . . ?
C8 N1 Fe1 117.29(14) . . ?
C9 N2 C10 114.3(2) . . ?
C9 N2 Fe1 108.13(15) . . ?
C10 N2 Fe1 111.16(17) . . ?
C12 N3 C11 121.0(2) . . ?
C12 N3 Fe1 126.47(17) . . ?
C11 N3 Fe1 111.86(17) . . ?

_refine_diff_density_max         0.749
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.108



####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2036445'
loop_
_audit_author_name
_audit_author_address
'Shouvik Chattopadhyay'
;Jadavpur University, kolkata
India
;
_audit_update_record             
;
2020-10-10 deposited with the CCDC.	2021-01-26 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         ?
_chemical_formula_sum            'C18 H17 Br2 Fe N6 O2'
_chemical_formula_weight         565.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   12.7967(10)
_cell_length_b                   9.4429(7)
_cell_length_c                   17.7657(14)
_cell_angle_alpha                90
_cell_angle_beta                 108.017(3)
_cell_angle_gamma                90
_cell_volume                     2041.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    900
_cell_measurement_theta_min      2.346
_cell_measurement_theta_max      26.517

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            GREEN
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.838
_exptl_crystal_F_000             1116
_exptl_transmission_factor_min   0.075
_exptl_transmission_factor_max   0.392
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    4.681
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8 QUEST AREA DETECTOR'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27652
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.346
_diffrn_reflns_theta_max         26.517
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4215
_reflns_number_gt                3407
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0323P)²+2.9702P] 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         4215
_refine_ls_number_parameters     266
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0890
_refine_ls_wR_factor_gt          0.0820
_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 0.22022(4) 0.53838(5) 0.55701(3) 0.03265(12) Uani 1 1 d . . . . .
C1 C 0.1235(2) 0.4814(3) 0.68347(18) 0.0327(7) Uani 1 1 d . . . . .
C2 C 0.0977(3) 0.3748(4) 0.7293(2) 0.0406(8) Uani 1 1 d . . . . .
H2 H 0.086832 0.282866 0.709582 0.049 Uiso 1 1 calc R U . . .
C3 C 0.0878(3) 0.4026(4) 0.8028(2) 0.0436(8) Uani 1 1 d . . . . .
H3 H 0.069525 0.330142 0.831950 0.052 Uiso 1 1 calc R U . . .
C4 C 0.1053(3) 0.5390(4) 0.83359(19) 0.0410(8) Uani 1 1 d . . . . .
C5 C 0.1328(3) 0.6464(4) 0.7918(2) 0.0401(8) Uani 1 1 d . . . . .
H5 H 0.145283 0.736952 0.813280 0.048 Uiso 1 1 calc R U . . .
C6 C 0.1420(2) 0.6197(3) 0.71615(19) 0.0353(7) Uani 1 1 d . . . . .
C7 C 0.1545(3) 0.7393(3) 0.6686(2) 0.0384(7) Uani 1 1 d . . . . .
H7 H 0.146632 0.829728 0.686827 0.046 Uiso 1 1 calc R U . . .
C8 C 0.1617(3) 0.8487(4) 0.5501(2) 0.0433(8) Uani 1 1 d . . . . .
H8A H 0.231658 0.876780 0.544219 0.052 Uiso 1 1 calc R U . . .
H8B H 0.130870 0.928619 0.570258 0.052 Uiso 1 1 calc R U . . .
C9 C 0.0834(3) 0.7992(4) 0.4712(2) 0.0455(8) Uani 1 1 d . . . . .
H9A H 0.008936 0.797357 0.474148 0.055 Uiso 1 1 calc R U . . .
H9B H 0.085531 0.865293 0.429931 0.055 Uiso 1 1 calc R U . . .
C10 C 0.1739(3) 0.6553(4) 0.3926(2) 0.0489(9) Uani 1 1 d . . . . .
H10A H 0.136227 0.714843 0.347957 0.059 Uiso 1 1 calc R U . . .
H10B H 0.176169 0.559616 0.373224 0.059 Uiso 1 1 calc R U . . .
C11 C 0.2892(3) 0.7089(4) 0.4300(2) 0.0468(9) Uani 1 1 d . . . . .
H11A H 0.334002 0.686123 0.396460 0.056 Uiso 1 1 calc R U . . .
H11B H 0.288287 0.811043 0.435655 0.056 Uiso 1 1 calc R U . . .
C12 C 0.4405(3) 0.6439(4) 0.5367(2) 0.0399(8) Uani 1 1 d . . . . .
H12 H 0.479730 0.679627 0.504776 0.048 Uiso 1 1 calc R U . . .
C13 C 0.5032(3) 0.5948(3) 0.6142(2) 0.0364(7) Uani 1 1 d . . . . .
C14 C 0.6169(3) 0.6226(4) 0.6397(2) 0.0447(8) Uani 1 1 d . . . . .
H14 H 0.649062 0.666163 0.605441 0.054 Uiso 1 1 calc R U . . .
C15 C 0.6803(3) 0.5864(4) 0.7141(2) 0.0451(9) Uani 1 1 d . . . . .
C16 C 0.6338(3) 0.5195(4) 0.7652(2) 0.0493(9) Uani 1 1 d . . . . .
H16 H 0.677775 0.493272 0.815528 0.059 Uiso 1 1 calc R U . . .
C17 C 0.5231(3) 0.4917(4) 0.7421(2) 0.0465(9) Uani 1 1 d . . . . .
H17 H 0.493081 0.447337 0.777366 0.056 Uiso 1 1 calc R U . . .
C18 C 0.4538(3) 0.5286(3) 0.6662(2) 0.0371(7) Uani 1 1 d . . . . .
Br1 Br 0.08517(4) 0.57332(5) 0.93386(2) 0.06057(14) Uani 1 1 d . . . . .
Br2 Br 0.83234(3) 0.63072(6) 0.74913(3) 0.07131(17) Uani 1 1 d . . . . .
O2 O 0.34827(18) 0.5022(3) 0.64760(14) 0.0422(6) Uani 1 1 d . . . . .
O1 O 0.12412(18) 0.4512(2) 0.61099(13) 0.0362(5) Uani 1 1 d . . . . .
N1 N 0.1757(2) 0.7281(3) 0.60326(16) 0.0343(6) Uani 1 1 d . . . . .
N2 N 0.1139(2) 0.6565(3) 0.45126(17) 0.0407(7) Uani 1 1 d D . . . .
N3 N 0.3362(2) 0.6430(3) 0.50799(16) 0.0376(6) Uani 1 1 d . . . . .
N4 N 0.2157(3) 0.3714(3) 0.4879(2) 0.0598(9) Uani 1 1 d . . . . .
N5 N 0.1631(3) 0.2694(3) 0.46291(19) 0.0501(8) Uani 1 1 d . . . . .
N6 N 0.1178(4) 0.1676(5) 0.4378(3) 0.0934(15) Uani 1 1 d . . . . .
H2A H 0.056(2) 0.607(4) 0.434(2) 0.067(14) Uiso 1 1 d 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 1.939(2) . ?
Fe1 O1 1.959(2) . ?
Fe1 N4 1.988(3) . ?
Fe1 N1 2.121(3) . ?
Fe1 N3 2.177(3) . ?
Fe1 N2 2.246(3) . ?
C1 O1 1.321(4) . ?
C1 C2 1.397(5) . ?
C1 C6 1.419(5) . ?
C2 C3 1.377(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(5) . ?
C4 Br1 1.905(3) . ?
C5 C6 1.408(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.448(5) . ?
C7 N1 1.275(4) . ?
C7 H7 0.9300 . ?
C8 N1 1.454(4) . ?
C8 C9 1.522(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N2 1.476(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.474(5) . ?
C10 C11 1.506(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N3 1.467(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N3 1.272(4) . ?
C12 C13 1.438(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.408(4) . ?
C13 C18 1.416(5) . ?
C14 C15 1.364(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(6) . ?
C15 Br2 1.897(3) . ?
C16 C17 1.373(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.410(5) . ?
C17 H17 0.9300 . ?
C18 O2 1.311(4) . ?
N2 H2A 0.848(19) . ?
N4 N5 1.180(4) . ?
N5 N6 1.140(5) . ?

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 90.98(9) . . ?
O2 Fe1 N4 103.23(14) . . ?
O1 Fe1 N4 93.80(12) . . ?
O2 Fe1 N1 94.97(10) . . ?
O1 Fe1 N1 83.14(10) . . ?
N4 Fe1 N1 161.61(14) . . ?
O2 Fe1 N3 84.62(10) . . ?
O1 Fe1 N3 174.54(10) . . ?
N4 Fe1 N3 90.36(12) . . ?
N1 Fe1 N3 94.00(10) . . ?
O2 Fe1 N2 156.84(10) . . ?
O1 Fe1 N2 107.98(10) . . ?
N4 Fe1 N2 89.01(14) . . ?
N1 Fe1 N2 74.85(11) . . ?
N3 Fe1 N2 75.60(11) . . ?
O1 C1 C2 119.1(3) . . ?
O1 C1 C6 123.1(3) . . ?
C2 C1 C6 117.7(3) . . ?
C3 C2 C1 121.6(3) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 Br1 121.0(3) . . ?
C3 C4 Br1 118.2(3) . . ?
C4 C5 C6 119.9(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 C7 118.3(3) . . ?
C1 C6 C7 120.9(3) . . ?
N1 C7 C6 124.0(3) . . ?
N1 C7 H7 118.0 . . ?
C6 C7 H7 118.0 . . ?
N1 C8 C9 105.7(3) . . ?
N1 C8 H8A 110.6 . . ?
C9 C8 H8A 110.6 . . ?
N1 C8 H8B 110.6 . . ?
C9 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
N2 C9 C8 110.7(3) . . ?
N2 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N2 C10 C11 109.8(3) . . ?
N2 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
N2 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
N3 C11 C10 109.5(3) . . ?
N3 C11 H11A 109.8 . . ?
C10 C11 H11A 109.8 . . ?
N3 C11 H11B 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
N3 C12 C13 126.0(3) . . ?
N3 C12 H12 117.0 . . ?
C13 C12 H12 117.0 . . ?
C14 C13 C18 119.8(3) . . ?
C14 C13 C12 117.6(3) . . ?
C18 C13 C12 122.4(3) . . ?
C15 C14 C13 120.8(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 120.2(3) . . ?
C14 C15 Br2 120.3(3) . . ?
C16 C15 Br2 119.4(3) . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 121.7(4) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
O2 C18 C17 119.2(3) . . ?
O2 C18 C13 123.6(3) . . ?
C17 C18 C13 117.2(3) . . ?
C18 O2 Fe1 135.7(2) . . ?
C1 O1 Fe1 125.48(19) . . ?
C7 N1 C8 120.6(3) . . ?
C7 N1 Fe1 125.5(2) . . ?
C8 N1 Fe1 113.8(2) . . ?
C10 N2 C9 114.3(3) . . ?
C10 N2 Fe1 105.9(2) . . ?
C9 N2 Fe1 112.9(2) . . ?
C10 N2 H2A 110(3) . . ?
C9 N2 H2A 108(3) . . ?
Fe1 N2 H2A 105(3) . . ?
C12 N3 C11 116.7(3) . . ?
C12 N3 Fe1 127.0(2) . . ?
C11 N3 Fe1 116.0(2) . . ?
N5 N4 Fe1 141.6(3) . . ?
N6 N5 N4 175.9(4) . . ?

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 C1 C2 C3 -175.1(3) . . . . ?
C6 C1 C2 C3 1.4(5) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C2 C3 C4 Br1 177.6(3) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
Br1 C4 C5 C6 -177.0(2) . . . . ?
C4 C5 C6 C1 -0.3(5) . . . . ?
C4 C5 C6 C7 170.7(3) . . . . ?
O1 C1 C6 C5 175.6(3) . . . . ?
C2 C1 C6 C5 -0.8(4) . . . . ?
O1 C1 C6 C7 4.8(5) . . . . ?
C2 C1 C6 C7 -171.6(3) . . . . ?
C5 C6 C7 N1 172.0(3) . . . . ?
C1 C6 C7 N1 -17.1(5) . . . . ?
N1 C8 C9 N2 -44.5(4) . . . . ?
N2 C10 C11 N3 45.1(4) . . . . ?
N3 C12 C13 C14 -171.2(3) . . . . ?
N3 C12 C13 C18 4.7(6) . . . . ?
C18 C13 C14 C15 0.1(5) . . . . ?
C12 C13 C14 C15 176.2(3) . . . . ?
C13 C14 C15 C16 1.1(6) . . . . ?
C13 C14 C15 Br2 -177.7(3) . . . . ?
C14 C15 C16 C17 -1.4(6) . . . . ?
Br2 C15 C16 C17 177.4(3) . . . . ?
C15 C16 C17 C18 0.5(6) . . . . ?
C16 C17 C18 O2 -178.7(3) . . . . ?
C16 C17 C18 C13 0.6(5) . . . . ?
C14 C13 C18 O2 178.3(3) . . . . ?
C12 C13 C18 O2 2.4(5) . . . . ?
C14 C13 C18 C17 -0.9(5) . . . . ?
C12 C13 C18 C17 -176.8(3) . . . . ?
C17 C18 O2 Fe1 176.3(3) . . . . ?
C13 C18 O2 Fe1 -2.9(5) . . . . ?
C2 C1 O1 Fe1 -148.0(2) . . . . ?
C6 C1 O1 Fe1 35.7(4) . . . . ?
C6 C7 N1 C8 165.5(3) . . . . ?
C6 C7 N1 Fe1 -9.4(5) . . . . ?
C9 C8 N1 C7 -123.8(3) . . . . ?
C9 C8 N1 Fe1 51.7(3) . . . . ?
C11 C10 N2 C9 72.6(4) . . . . ?
C11 C10 N2 Fe1 -52.4(3) . . . . ?
C8 C9 N2 C10 -101.5(3) . . . . ?
C8 C9 N2 Fe1 19.7(3) . . . . ?
C13 C12 N3 C11 175.3(3) . . . . ?
C13 C12 N3 Fe1 -10.5(5) . . . . ?
C10 C11 N3 C12 160.1(3) . . . . ?
C10 C11 N3 Fe1 -14.8(4) . . . . ?

_refine_diff_density_max         1.357
_refine_diff_density_min         -1.165
_refine_diff_density_rms         0.073



