# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2036380'
loop_
_audit_author_name
_audit_author_address
'Shouvik Chattopadhyay'
;Jadavpur University, kolkata
India
;
_audit_update_record             
;
2020-10-09 deposited with the CCDC.	2020-12-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 Fe N5 O S2'
_chemical_formula_weight         392.30

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'
S S 0.1246 0.1234 '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'

_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                   11.6962(10)
_cell_length_b                   12.7639(10)
_cell_length_c                   12.7562(10)
_cell_angle_alpha                90
_cell_angle_beta                 112.592(2)
_cell_angle_gamma                90
_cell_volume                     1758.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    900
_cell_measurement_theta_min      2.06
_cell_measurement_theta_max      25.27

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_F_000             812
_exptl_transmission_factor_min   0.690
_exptl_transmission_factor_max   0.800
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    1.105
_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            24912
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.353
_diffrn_reflns_theta_max         27.155
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3891
_reflns_number_gt                3167
_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-2018/1 (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)+(0.0571P)²+0.4412P] 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         3891
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.133
_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 0.35774(3) 0.61294(2) 0.74105(3) 0.04433(13) Uani 1 1 d . . . . .
S1 S 0.56532(8) 0.28615(6) 0.86786(7) 0.0720(2) Uani 1 1 d . . . . .
S2 S 0.12820(8) 0.46323(8) 0.94187(7) 0.0792(3) Uani 1 1 d . . . . .
O1 O 0.25695(17) 0.55979(15) 0.59992(15) 0.0582(5) Uani 1 1 d . . . . .
N3 N 0.47980(18) 0.66597(14) 0.66273(18) 0.0485(5) Uani 1 1 d . . . . .
N2 N 0.4850(2) 0.70942(16) 0.8742(2) 0.0535(5) Uani 1 1 d . . . . .
N1 N 0.2598(3) 0.76065(19) 0.7137(2) 0.0564(6) Uani 1 1 d . . . . .
N4 N 0.4691(2) 0.48479(17) 0.8106(2) 0.0617(6) Uani 1 1 d . . . . .
N5 N 0.2508(2) 0.56865(19) 0.8271(2) 0.0625(6) Uani 1 1 d . . . . .
C12 C 0.2676(2) 0.54906(17) 0.5009(2) 0.0466(5) Uani 1 1 d . . . . .
C11 C 0.1762(3) 0.4905(2) 0.4179(2) 0.0572(6) Uani 1 1 d . . . . .
H17 H 0.113977 0.459242 0.435503 0.069 Uiso 1 1 calc R U . . .
C10 C 0.1760(3) 0.4782(2) 0.3110(2) 0.0695(8) Uani 1 1 d . . . . .
H1 H 0.114258 0.438831 0.257074 0.083 Uiso 1 1 calc R U . . .
C9 C 0.2666(4) 0.5237(3) 0.2844(3) 0.0798(10) Uani 1 1 d . . . . .
H16 H 0.266482 0.516175 0.211858 0.096 Uiso 1 1 calc R U . . .
C8 C 0.3579(3) 0.5808(3) 0.3646(3) 0.0700(8) Uani 1 1 d . . . . .
H8 H 0.419462 0.610474 0.344828 0.084 Uiso 1 1 calc R U . . .
C7 C 0.3627(2) 0.59642(19) 0.4750(2) 0.0503(6) Uani 1 1 d . . . . .
C5 C 0.4643(2) 0.65864(18) 0.5565(2) 0.0522(6) Uani 1 1 d . . . . .
C4 C 0.5868(3) 0.7255(2) 0.7402(3) 0.0646(7) Uani 1 1 d . . . . .
H12 H 0.573039 0.799871 0.724897 0.077 Uiso 1 1 calc R U . . .
H11 H 0.660725 0.705705 0.727803 0.077 Uiso 1 1 calc R U . . .
C3 C 0.6051(3) 0.7034(2) 0.8623(3) 0.0675(8) Uani 1 1 d . . . . .
H10 H 0.640522 0.634126 0.883939 0.081 Uiso 1 1 calc R U . . .
H9 H 0.661935 0.754186 0.912068 0.081 Uiso 1 1 calc R U . . .
C2 C 0.4386(3) 0.8180(2) 0.8713(3) 0.0608(7) Uani 1 1 d . . . . .
H3 H 0.467191 0.861644 0.824061 0.073 Uiso 1 1 calc R U . . .
H6 H 0.469557 0.847217 0.947339 0.073 Uiso 1 1 calc R U . . .
C1 C 0.2993(3) 0.8155(2) 0.8239(2) 0.0611(7) Uani 1 1 d . . . . .
H5 H 0.269923 0.778399 0.875106 0.073 Uiso 1 1 calc R U . . .
H4 H 0.266189 0.886095 0.813528 0.073 Uiso 1 1 calc R U . . .
C6 C 0.5510(3) 0.7157(3) 0.5131(3) 0.0815(10) Uani 1 1 d . . . . .
H15 H 0.576063 0.780834 0.553052 0.122 Uiso 1 1 calc R U . . .
H13 H 0.509042 0.729357 0.433366 0.122 Uiso 1 1 calc R U . . .
H14 H 0.622634 0.673192 0.525320 0.122 Uiso 1 1 calc R U . . .
C13 C 0.5088(2) 0.4033(2) 0.8353(2) 0.0508(6) Uani 1 1 d . . . . .
C14 C 0.1999(2) 0.5248(2) 0.8752(2) 0.0504(6) Uani 1 1 d . . . . .
H2 H 0.493(3) 0.683(2) 0.933(3) 0.062(9) Uiso 1 1 d . . . . .
H1N H 0.279(3) 0.804(2) 0.661(3) 0.062(8) Uiso 1 1 d . . . . .
H2N H 0.192(3) 0.745(3) 0.686(3) 0.066(10) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 O1 1.8602(17) . ?
Fe1 N5 2.035(2) . ?
Fe1 N4 2.067(2) . ?
Fe1 N3 2.143(2) . ?
Fe1 N2 2.162(2) . ?
Fe1 N1 2.164(2) . ?
S1 C13 1.623(3) . ?
S2 C14 1.610(3) . ?
O1 C12 1.323(3) . ?
N3 C5 1.300(3) . ?
N3 C4 1.474(3) . ?
N2 C3 1.472(4) . ?
N2 C2 1.484(3) . ?
N2 H2 0.80(3) . ?
N1 C1 1.476(4) . ?
N1 H1N 0.96(3) . ?
N1 H2N 0.76(3) . ?
N4 C13 1.133(3) . ?
N5 C14 1.152(3) . ?
C12 C11 1.398(4) . ?
C12 C7 1.413(4) . ?
C11 C10 1.371(4) . ?
C11 H17 0.9300 . ?
C10 C9 1.362(5) . ?
C10 H1 0.9300 . ?
C9 C8 1.370(5) . ?
C9 H16 0.9300 . ?
C8 C7 1.402(4) . ?
C8 H8 0.9300 . ?
C7 C5 1.475(4) . ?
C5 C6 1.515(4) . ?
C4 C3 1.515(4) . ?
C4 H12 0.9700 . ?
C4 H11 0.9700 . ?
C3 H10 0.9700 . ?
C3 H9 0.9700 . ?
C2 C1 1.505(4) . ?
C2 H3 0.9700 . ?
C2 H6 0.9700 . ?
C1 H5 0.9700 . ?
C1 H4 0.9700 . ?
C6 H15 0.9600 . ?
C6 H13 0.9600 . ?
C6 H14 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Fe1 N5 97.37(9) . . ?
O1 Fe1 N4 100.79(9) . . ?
N5 Fe1 N4 88.03(10) . . ?
O1 Fe1 N3 87.25(8) . . ?
N5 Fe1 N3 175.36(9) . . ?
N4 Fe1 N3 91.54(8) . . ?
O1 Fe1 N2 163.16(9) . . ?
N5 Fe1 N2 96.59(10) . . ?
N4 Fe1 N2 89.05(9) . . ?
N3 Fe1 N2 78.78(9) . . ?
O1 Fe1 N1 93.57(9) . . ?
N5 Fe1 N1 86.11(11) . . ?
N4 Fe1 N1 165.08(10) . . ?
N3 Fe1 N1 93.19(9) . . ?
N2 Fe1 N1 78.02(9) . . ?
C12 O1 Fe1 134.81(16) . . ?
C5 N3 C4 118.6(2) . . ?
C5 N3 Fe1 127.78(18) . . ?
C4 N3 Fe1 113.37(17) . . ?
C3 N2 C2 113.7(2) . . ?
C3 N2 Fe1 106.58(17) . . ?
C2 N2 Fe1 112.18(17) . . ?
C3 N2 H2 108(2) . . ?
C2 N2 H2 109(2) . . ?
Fe1 N2 H2 107(2) . . ?
C1 N1 Fe1 107.86(17) . . ?
C1 N1 H1N 108.9(18) . . ?
Fe1 N1 H1N 111.1(18) . . ?
C1 N1 H2N 117(2) . . ?
Fe1 N1 H2N 104(3) . . ?
H1N N1 H2N 108(3) . . ?
C13 N4 Fe1 165.7(2) . . ?
C14 N5 Fe1 166.7(2) . . ?
O1 C12 C11 117.0(2) . . ?
O1 C12 C7 123.4(2) . . ?
C11 C12 C7 119.6(2) . . ?
C10 C11 C12 121.6(3) . . ?
C10 C11 H17 119.2 . . ?
C12 C11 H17 119.2 . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 H1 120.2 . . ?
C11 C10 H1 120.2 . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 H16 120.0 . . ?
C8 C9 H16 120.0 . . ?
C9 C8 C7 123.0(3) . . ?
C9 C8 H8 118.5 . . ?
C7 C8 H8 118.5 . . ?
C8 C7 C12 116.3(3) . . ?
C8 C7 C5 119.7(3) . . ?
C12 C7 C5 124.0(2) . . ?
N3 C5 C7 121.7(2) . . ?
N3 C5 C6 120.1(3) . . ?
C7 C5 C6 118.2(3) . . ?
N3 C4 C3 110.0(2) . . ?
N3 C4 H12 109.7 . . ?
C3 C4 H12 109.7 . . ?
N3 C4 H11 109.7 . . ?
C3 C4 H11 109.7 . . ?
H12 C4 H11 108.2 . . ?
N2 C3 C4 109.4(2) . . ?
N2 C3 H10 109.8 . . ?
C4 C3 H10 109.8 . . ?
N2 C3 H9 109.8 . . ?
C4 C3 H9 109.8 . . ?
H10 C3 H9 108.2 . . ?
N2 C2 C1 108.6(2) . . ?
N2 C2 H3 110.0 . . ?
C1 C2 H3 110.0 . . ?
N2 C2 H6 110.0 . . ?
C1 C2 H6 110.0 . . ?
H3 C2 H6 108.3 . . ?
N1 C1 C2 106.7(2) . . ?
N1 C1 H5 110.4 . . ?
C2 C1 H5 110.4 . . ?
N1 C1 H4 110.4 . . ?
C2 C1 H4 110.4 . . ?
H5 C1 H4 108.6 . . ?
C5 C6 H15 109.5 . . ?
C5 C6 H13 109.5 . . ?
H15 C6 H13 109.5 . . ?
C5 C6 H14 109.5 . . ?
H15 C6 H14 109.5 . . ?
H13 C6 H14 109.5 . . ?
N4 C13 S1 178.7(3) . . ?
N5 C14 S2 179.7(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
N5 Fe1 O1 C12 -172.9(2) . . . . ?
N4 Fe1 O1 C12 -83.5(2) . . . . ?
N3 Fe1 O1 C12 7.6(2) . . . . ?
N2 Fe1 O1 C12 41.4(5) . . . . ?
N1 Fe1 O1 C12 100.6(2) . . . . ?
Fe1 O1 C12 C11 171.05(18) . . . . ?
Fe1 O1 C12 C7 -11.3(4) . . . . ?
O1 C12 C11 C10 177.4(2) . . . . ?
C7 C12 C11 C10 -0.3(4) . . . . ?
C12 C11 C10 C9 0.0(4) . . . . ?
C11 C10 C9 C8 0.6(5) . . . . ?
C10 C9 C8 C7 -0.8(5) . . . . ?
C9 C8 C7 C12 0.4(4) . . . . ?
C9 C8 C7 C5 179.8(3) . . . . ?
O1 C12 C7 C8 -177.5(2) . . . . ?
C11 C12 C7 C8 0.1(3) . . . . ?
O1 C12 C7 C5 3.2(4) . . . . ?
C11 C12 C7 C5 -179.2(2) . . . . ?
C4 N3 C5 C7 177.2(2) . . . . ?
Fe1 N3 C5 C7 -9.0(3) . . . . ?
C4 N3 C5 C6 -3.5(3) . . . . ?
Fe1 N3 C5 C6 170.35(19) . . . . ?
C8 C7 C5 N3 -172.7(2) . . . . ?
C12 C7 C5 N3 6.7(4) . . . . ?
C8 C7 C5 C6 8.0(4) . . . . ?
C12 C7 C5 C6 -172.7(2) . . . . ?
C5 N3 C4 C3 -166.7(2) . . . . ?
Fe1 N3 C4 C3 18.6(3) . . . . ?
C2 N2 C3 C4 -73.9(3) . . . . ?
Fe1 N2 C3 C4 50.2(2) . . . . ?
N3 C4 C3 N2 -46.0(3) . . . . ?
C3 N2 C2 C1 150.9(2) . . . . ?
Fe1 N2 C2 C1 29.9(3) . . . . ?
Fe1 N1 C1 C2 52.2(3) . . . . ?
N2 C2 C1 N1 -54.1(3) . . . . ?

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.116

####################################################################### 
# 
# 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 2036381'
loop_
_audit_author_name
_audit_author_address
'Shouvik Chattopadhyay'
;Jadavpur University, kolkata
India
;
_audit_update_record             
;
2020-10-09 deposited with the CCDC.	2020-12-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H20 Cl Fe N6 O'
_chemical_formula_weight         367.65

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'
Nb Nb -2.0727 0.6215 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   11.143(3)
_cell_length_b                   13.276(3)
_cell_length_c                   11.981(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.225(6)
_cell_angle_gamma                90
_cell_volume                     1683.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    900
_cell_measurement_theta_min      2.06
_cell_measurement_theta_max      22.57

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             764
_exptl_transmission_factor_min   0.689
_exptl_transmission_factor_max   0.808
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    1.064
_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            16196
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.180
_diffrn_reflns_theta_max         24.987
_diffrn_reflns_theta_full        24.987
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2923
_reflns_number_gt                2234
_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-2018/1 (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)+(0.1171P)²+4.1855P] 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         2923
_refine_ls_number_parameters     213
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0787
_refine_ls_wR_factor_ref         0.2336
_refine_ls_wR_factor_gt          0.2050
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.5278(3) 0.5995(3) 0.1823(2) 0.1031(9) Uani 0.806(4) 1 d . . P A 1
Cl1A Cl 0.4808(11) 0.7197(10) 0.2075(9) 0.1031(9) Uani 0.194(4) 1 d . . P A 2
Fe1 Fe 0.64764(8) 0.44981(6) 0.23481(7) 0.0564(4) Uani 1 1 d . . . . .
N4 N 0.7544(6) 0.4894(5) 0.1279(5) 0.0744(15) Uani 1 1 d . . . . .
N2 N 0.5064(5) 0.3613(4) 0.1057(4) 0.0653(14) Uani 1 1 d . . . . .
H2 H 0.489492 0.394348 0.029230 0.078 Uiso 1 1 calc R U . . .
N3 N 0.5377(4) 0.3886(3) 0.3389(4) 0.0553(11) Uani 1 1 d . . . . .
O1 O 0.7572(5) 0.4973(3) 0.3770(3) 0.0734(13) Uani 1 1 d . . . . .
N5 N 0.7957(5) 0.5661(4) 0.1252(4) 0.0618(13) Uani 1 1 d . . . . .
N6 N 0.8430(6) 0.6453(5) 0.1183(5) 0.0826(17) Uani 1 1 d . . . . .
C2 C 0.5511(8) 0.2567(5) 0.0950(6) 0.083(2) Uani 1 1 d . . . . .
H2A H 0.512996 0.232309 0.015407 0.100 Uiso 1 1 calc R U . . .
H2B H 0.526383 0.212117 0.148073 0.100 Uiso 1 1 calc R U . . .
C1 C 0.6939(9) 0.2573(5) 0.1251(7) 0.085(2) Uani 1 1 d . . . . .
H1A H 0.725833 0.189079 0.128172 0.102 Uiso 1 1 calc R U . . .
H1B H 0.718935 0.294588 0.066269 0.102 Uiso 1 1 calc R U . . .
N1 N 0.7443(8) 0.3064(4) 0.2413(6) 0.0734(16) Uani 1 1 d D . . . .
C3 C 0.3904(6) 0.3653(5) 0.1387(6) 0.0741(18) Uani 1 1 d . . . . .
H3A H 0.328988 0.318260 0.091099 0.089 Uiso 1 1 calc R U . . .
H3B H 0.354496 0.432474 0.124530 0.089 Uiso 1 1 calc R U . . .
C4 C 0.4196(6) 0.3389(5) 0.2676(6) 0.0702(17) Uani 1 1 d . . . . .
H4A H 0.350254 0.360175 0.294765 0.084 Uiso 1 1 calc R U . . .
H4B H 0.428508 0.266440 0.277397 0.084 Uiso 1 1 calc R U . . .
C5 C 0.5678(6) 0.3807(4) 0.4520(5) 0.0559(13) Uani 1 1 d . . . . .
C6 C 0.4849(7) 0.3262(5) 0.5098(6) 0.0791(19) Uani 1 1 d . . . . .
H6A H 0.401413 0.319524 0.455002 0.119 Uiso 1 1 calc R U . . .
H6B H 0.480980 0.363597 0.577119 0.119 Uiso 1 1 calc R U . . .
H6C H 0.519212 0.260494 0.534130 0.119 Uiso 1 1 calc R U . . .
C7 C 0.6872(6) 0.4251(4) 0.5308(5) 0.0547(13) Uani 1 1 d . . . . .
C13 C 0.7727(6) 0.4814(4) 0.4891(5) 0.0571(14) Uani 1 1 d . . . . .
C12 C 0.8790(6) 0.5232(5) 0.5718(6) 0.0664(16) Uani 1 1 d . . . . .
H12 H 0.934577 0.561040 0.544914 0.080 Uiso 1 1 calc R U . . .
C11 C 0.9047(7) 0.5111(5) 0.6895(5) 0.0698(17) Uani 1 1 d . . . . .
H11 H 0.976470 0.540582 0.741027 0.084 Uiso 1 1 calc R U . . .
C9 C 0.8236(7) 0.4545(5) 0.7336(6) 0.0660(16) Uani 1 1 d . . . . .
C10 C 0.8513(8) 0.4410(6) 0.8643(6) 0.087(2) Uani 1 1 d . . . . .
H10A H 0.785265 0.401845 0.878842 0.130 Uiso 1 1 calc R U . . .
H10B H 0.855631 0.505741 0.900990 0.130 Uiso 1 1 calc R U . . .
H10C H 0.930536 0.406739 0.896182 0.130 Uiso 1 1 calc R U . . .
C8 C 0.7178(6) 0.4139(4) 0.6531(5) 0.0617(14) Uani 1 1 d . . . . .
H8 H 0.663150 0.376498 0.681609 0.074 Uiso 1 1 calc R U . . .
H2N H 0.720(9) 0.275(6) 0.298(6) 0.12(3) Uiso 1 1 d D . . . .
H1N H 0.812(6) 0.313(5) 0.253(5) 0.044(19) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 Fe1 2.367(3) . ?
Fe1 O1 1.868(4) . ?
Fe1 N4 2.071(6) . ?
Fe1 N3 2.161(5) . ?
Fe1 N2 2.174(5) . ?
Fe1 N1 2.177(6) . ?
N4 N5 1.122(7) . ?
N2 C3 1.466(9) . ?
N2 C2 1.494(8) . ?
N2 H2 0.9800 . ?
N3 C5 1.295(7) . ?
N3 C4 1.481(8) . ?
O1 C13 1.317(7) . ?
N5 N6 1.191(8) . ?
C2 C1 1.518(12) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1 N1 1.480(9) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
N1 H2N 0.91(2) . ?
N1 H1N 0.73(6) . ?
C3 C4 1.516(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C7 1.490(8) . ?
C5 C6 1.503(8) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.404(8) . ?
C7 C13 1.419(8) . ?
C13 C12 1.400(8) . ?
C12 C11 1.358(9) . ?
C12 H12 0.9300 . ?
C11 C9 1.400(10) . ?
C11 H11 0.9300 . ?
C9 C8 1.379(9) . ?
C9 C10 1.509(9) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C8 H8 0.9300 . ?

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 N4 98.1(2) . . ?
O1 Fe1 N3 85.85(18) . . ?
N4 Fe1 N3 172.5(2) . . ?
O1 Fe1 N2 162.25(19) . . ?
N4 Fe1 N2 97.2(2) . . ?
N3 Fe1 N2 78.02(19) . . ?
O1 Fe1 N1 95.0(2) . . ?
N4 Fe1 N1 82.6(3) . . ?
N3 Fe1 N1 90.8(2) . . ?
N2 Fe1 N1 78.0(2) . . ?
O1 Fe1 Cl1 96.45(17) . . ?
N4 Fe1 Cl1 90.47(19) . . ?
N3 Fe1 Cl1 95.41(14) . . ?
N2 Fe1 Cl1 92.43(15) . . ?
N1 Fe1 Cl1 167.30(19) . . ?
N5 N4 Fe1 124.6(5) . . ?
C3 N2 C2 113.8(6) . . ?
C3 N2 Fe1 106.9(4) . . ?
C2 N2 Fe1 112.1(4) . . ?
C3 N2 H2 107.9 . . ?
C2 N2 H2 107.9 . . ?
Fe1 N2 H2 107.9 . . ?
C5 N3 C4 117.4(5) . . ?
C5 N3 Fe1 128.8(4) . . ?
C4 N3 Fe1 113.4(4) . . ?
C13 O1 Fe1 135.7(4) . . ?
N4 N5 N6 176.3(7) . . ?
N2 C2 C1 109.1(6) . . ?
N2 C2 H2A 109.9 . . ?
C1 C2 H2A 109.9 . . ?
N2 C2 H2B 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
N1 C1 C2 106.7(6) . . ?
N1 C1 H1A 110.4 . . ?
C2 C1 H1A 110.4 . . ?
N1 C1 H1B 110.4 . . ?
C2 C1 H1B 110.4 . . ?
H1A C1 H1B 108.6 . . ?
C1 N1 Fe1 108.3(4) . . ?
C1 N1 H2N 113(6) . . ?
Fe1 N1 H2N 99(6) . . ?
C1 N1 H1N 108(5) . . ?
Fe1 N1 H1N 111(5) . . ?
H2N N1 H1N 117(8) . . ?
N2 C3 C4 109.8(5) . . ?
N2 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
N2 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
N3 C4 C3 110.7(5) . . ?
N3 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
N3 C5 C7 121.3(5) . . ?
N3 C5 C6 121.7(5) . . ?
C7 C5 C6 117.0(5) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C13 116.9(5) . . ?
C8 C7 C5 119.8(5) . . ?
C13 C7 C5 123.3(5) . . ?
O1 C13 C12 118.0(6) . . ?
O1 C13 C7 123.7(5) . . ?
C12 C13 C7 118.2(5) . . ?
C11 C12 C13 123.0(6) . . ?
C11 C12 H12 118.5 . . ?
C13 C12 H12 118.5 . . ?
C12 C11 C9 120.3(6) . . ?
C12 C11 H11 119.9 . . ?
C9 C11 H11 119.9 . . ?
C8 C9 C11 117.2(6) . . ?
C8 C9 C10 122.2(7) . . ?
C11 C9 C10 120.6(6) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C8 C7 124.4(6) . . ?
C9 C8 H8 117.8 . . ?
C7 C8 H8 117.8 . . ?

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
N4 Fe1 O1 C13 -161.1(6) . . . . ?
N3 Fe1 O1 C13 12.5(6) . . . . ?
N2 Fe1 O1 C13 -12.1(12) . . . . ?
N1 Fe1 O1 C13 -78.0(7) . . . . ?
Cl1 Fe1 O1 C13 107.5(6) . . . . ?
C3 N2 C2 C1 -150.3(6) . . . . ?
Fe1 N2 C2 C1 -28.8(7) . . . . ?
N2 C2 C1 N1 52.9(7) . . . . ?
C2 C1 N1 Fe1 -51.7(7) . . . . ?
C2 N2 C3 C4 74.1(7) . . . . ?
Fe1 N2 C3 C4 -50.3(6) . . . . ?
C5 N3 C4 C3 173.4(5) . . . . ?
Fe1 N3 C4 C3 -13.7(7) . . . . ?
N2 C3 C4 N3 42.7(7) . . . . ?
C4 N3 C5 C7 177.8(5) . . . . ?
Fe1 N3 C5 C7 6.2(8) . . . . ?
C4 N3 C5 C6 -1.9(8) . . . . ?
Fe1 N3 C5 C6 -173.5(5) . . . . ?
N3 C5 C7 C8 -179.1(5) . . . . ?
C6 C5 C7 C8 0.6(8) . . . . ?
N3 C5 C7 C13 2.4(9) . . . . ?
C6 C5 C7 C13 -177.9(6) . . . . ?
Fe1 O1 C13 C12 171.8(5) . . . . ?
Fe1 O1 C13 C7 -8.8(10) . . . . ?
C8 C7 C13 O1 179.2(5) . . . . ?
C5 C7 C13 O1 -2.2(9) . . . . ?
C8 C7 C13 C12 -1.4(8) . . . . ?
C5 C7 C13 C12 177.2(5) . . . . ?
O1 C13 C12 C11 -179.6(6) . . . . ?
C7 C13 C12 C11 1.0(10) . . . . ?
C13 C12 C11 C9 0.2(10) . . . . ?
C12 C11 C9 C8 -0.9(9) . . . . ?
C12 C11 C9 C10 -179.8(6) . . . . ?
C11 C9 C8 C7 0.4(9) . . . . ?
C10 C9 C8 C7 179.3(6) . . . . ?
C13 C7 C8 C9 0.7(9) . . . . ?
C5 C7 C8 C9 -177.9(5) . . . . ?

_refine_diff_density_max         1.503
_refine_diff_density_min         -0.972
_refine_diff_density_rms         0.104

