# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# 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 1922356'
loop_
_audit_author_name
_audit_author_address
'Ennio Zangrando'
;Department of Chemical and Pharmaceutical Sciences University of Trieste
Italy
;
_audit_update_record             
;
2019-06-11 deposited with the CCDC.	2020-03-25 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         'C32 H34 Cl2 Fe2 N6 O7, 2(Fe Cl4), 2(C2 H6 O)'
_chemical_formula_sum            'C36 H46 Cl10 Fe4 N6 O9'
_chemical_formula_weight         1284.69

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   13.612(3)
_cell_length_b                   13.537(2)
_cell_length_c                   14.409(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.931(6)
_cell_angle_gamma                90
_cell_volume                     2496.0(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2034
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      25.85

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_F_000             1300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.052
_exptl_absorpt_coefficient_mu    1.730
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18516
_diffrn_reflns_av_unetI/netI     0.0913
_diffrn_reflns_av_R_equivalents  0.1046
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.127
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             5264
_reflns_number_gt                4383
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0609P)²+35.8837P] 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         5264
_refine_ls_number_parameters     300
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0867
_refine_ls_wR_factor_ref         0.2273
_refine_ls_wR_factor_gt          0.2206
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.53953(8) 0.87697(7) 0.54568(7) 0.0147(3) Uani 1 1 d D . . . .
Cl1 Cl 0.41372(15) 0.77617(13) 0.44611(13) 0.0231(4) Uani 1 1 d . . . . .
N1 N 0.6523(5) 0.8756(4) 0.4743(4) 0.0157(12) Uani 1 1 d . . . . .
N2 N 0.4859(5) 0.8977(5) 0.6667(4) 0.0176(12) Uani 1 1 d . . . . .
N3 N 0.6769(4) 0.9348(4) 0.6609(4) 0.0134(11) Uani 1 1 d . . . . .
O1 O 0.8521(4) 0.9560(4) 0.6803(4) 0.0199(11) Uani 1 1 d . . . . .
O2 O 0.7210(4) 1.0156(4) 0.8104(4) 0.0191(11) Uani 1 1 d . . . . .
O3 O 0.6229(4) 0.7468(4) 0.6284(4) 0.0205(11) Uani 1 1 d D . . . .
H3 H 0.608(4) 0.6836(9) 0.623(3) 0.031 Uiso 1 1 d D U . . .
O4 O 0.5000 1.0000 0.5000 0.0157(14) Uani 1 2 d S . P . .
C1 C 0.6385(6) 0.8342(6) 0.3859(5) 0.0209(15) Uani 1 1 d . . . . .
H1 H 0.5820 0.7896 0.3591 0.025 Uiso 1 1 calc R U . . .
C2 C 0.7031(7) 0.8542(6) 0.3327(6) 0.0252(17) Uani 1 1 d . . . . .
H2 H 0.6912 0.8246 0.2700 0.030 Uiso 1 1 calc R U . . .
C3 C 0.7863(6) 0.9185(6) 0.3729(5) 0.0240(16) Uani 1 1 d . . . . .
H3A H 0.8311 0.9353 0.3372 0.029 Uiso 1 1 calc R U . . .
C4 C 0.8030(6) 0.9578(6) 0.4652(5) 0.0214(15) Uani 1 1 d . . . . .
H4 H 0.8609 1.0001 0.4947 0.026 Uiso 1 1 calc R U . . .
C5 C 0.7354(6) 0.9355(5) 0.5144(5) 0.0174(14) Uani 1 1 d . . . . .
C6 C 0.3984(6) 0.8561(6) 0.6769(6) 0.0224(15) Uani 1 1 d . . . . .
H6 H 0.3577 0.8113 0.6282 0.027 Uiso 1 1 calc R U . . .
C7 C 0.3686(6) 0.8782(6) 0.7560(6) 0.0247(16) Uani 1 1 d . . . . .
H7 H 0.3079 0.8484 0.7622 0.030 Uiso 1 1 calc R U . . .
C8 C 0.4268(7) 0.9441(6) 0.8271(6) 0.0268(17) Uani 1 1 d . . . . .
H8 H 0.4063 0.9600 0.8821 0.032 Uiso 1 1 calc R U . . .
C9 C 0.5146(7) 0.9861(6) 0.8173(6) 0.0242(16) Uani 1 1 d . . . . .
H9 H 0.5558 1.0315 0.8651 0.029 Uiso 1 1 calc R U . . .
C10 C 0.5421(6) 0.9607(5) 0.7354(5) 0.0179(14) Uani 1 1 d . . . . .
C11 C 0.6380(5) 1.0050(5) 0.7209(5) 0.0144(13) Uani 1 1 d . . . . .
H11 H 0.6204 1.0702 0.6865 0.017 Uiso 1 1 calc R U . . .
C12 C 0.7504(6) 0.9800(5) 0.6155(5) 0.0175(14) Uani 1 1 d . . . . .
H12 H 0.7409 1.0533 0.6103 0.021 Uiso 1 1 calc R U . . .
C13 C 0.6862(6) 0.7641(5) 0.7301(5) 0.0190(15) Uani 1 1 d D . . . .
H13A H 0.7376 0.7101 0.7541 0.023 Uiso 1 1 calc R U . . .
H13B H 0.6414 0.7659 0.7717 0.023 Uiso 1 1 calc R U . . .
C14 C 0.7421(6) 0.8616(5) 0.7365(5) 0.0161(14) Uani 1 1 d . . . . .
C15 C 0.8411(5) 0.8565(5) 0.7115(5) 0.0169(14) Uani 1 1 d . . . . .
H15A H 0.9016 0.8376 0.7699 0.020 Uiso 1 1 calc R U . . .
H15B H 0.8340 0.8086 0.6577 0.020 Uiso 1 1 calc R U . . .
C16 C 0.7606(6) 0.9171(5) 0.8372(5) 0.0168(14) Uani 1 1 d . . . . .
H16A H 0.7225 0.8839 0.8760 0.020 Uiso 1 1 calc R U . . .
H16B H 0.8359 0.9188 0.8770 0.020 Uiso 1 1 calc R U . . .
Fe2 Fe 0.53959(9) 0.74194(8) 0.02680(8) 0.0201(3) Uani 1 1 d . . . . .
Cl2 Cl 0.38702(15) 0.80644(14) 0.01195(14) 0.0243(4) Uani 1 1 d . . . . .
Cl3 Cl 0.66204(17) 0.85525(16) 0.05830(15) 0.0309(5) Uani 1 1 d . . . . .
Cl4 Cl 0.57843(16) 0.63944(15) 0.15260(14) 0.0283(4) Uani 1 1 d . . . . .
Cl5 Cl 0.53733(16) 0.66599(15) -0.10893(14) 0.0273(4) Uani 1 1 d . . . . .
C17 C 0.4252(6) 0.5628(6) 0.6245(6) 0.0271(17) Uani 1 1 d . . . . .
H17A H 0.3876 0.6111 0.5731 0.033 Uiso 1 1 calc R U . . .
H17B H 0.4065 0.5760 0.6840 0.033 Uiso 1 1 calc R U . . .
C18 C 0.3910(7) 0.4599(6) 0.5879(7) 0.0326(19) Uani 1 1 d . . . . .
H18A H 0.4197 0.4425 0.5362 0.049 Uiso 1 1 calc R U . . .
H18B H 0.3145 0.4571 0.5609 0.049 Uiso 1 1 calc R U . . .
H18C H 0.4166 0.4130 0.6428 0.049 Uiso 1 1 calc R U . . .
O5 O 0.5359(4) 0.5755(4) 0.6481(4) 0.0253(12) Uani 1 1 d . . . . .
H5A H 0.5680 0.5417 0.6983 0.038 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 O4 1.8041(10) . ?
Fe1 N1 2.119(6) . ?
Fe1 N2 2.125(6) . ?
Fe1 N3 2.180(6) . ?
Fe1 O3 2.212(5) . ?
Fe1 Cl1 2.276(2) . ?
N1 C1 1.345(9) . ?
N1 C5 1.352(9) . ?
N2 C10 1.333(10) . ?
N2 C6 1.370(10) . ?
N3 C11 1.496(8) . ?
N3 C12 1.500(9) . ?
N3 C14 1.516(9) . ?
O1 C12 1.418(9) . ?
O1 C15 1.445(8) . ?
O2 C11 1.403(8) . ?
O2 C16 1.441(8) . ?
O3 C13 1.443(9) . ?
O3 H3 0.877(10) . ?
O4 Fe1 1.8040(10) 3_676 ?
C1 C2 1.377(11) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(11) . ?
C3 H3A 0.9500 . ?
C4 C5 1.371(10) . ?
C4 H4 0.9500 . ?
C5 C12 1.525(9) . ?
C6 C7 1.368(11) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(12) . ?
C7 H7 0.9500 . ?
C8 C9 1.374(12) . ?
C8 H8 0.9500 . ?
C9 C10 1.397(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.515(10) . ?
C11 H11 1.0000 . ?
C12 H12 1.0000 . ?
C13 C14 1.510(10) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.510(10) . ?
C14 C16 1.577(9) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
Fe2 Cl2 2.195(2) . ?
Fe2 Cl3 2.196(2) . ?
Fe2 Cl4 2.199(2) . ?
Fe2 Cl5 2.200(2) . ?
C17 O5 1.439(9) . ?
C17 C18 1.506(12) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O5 H5A 0.8400 . ?

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
O4 Fe1 N1 90.38(16) . . ?
O4 Fe1 N2 91.97(17) . . ?
N1 Fe1 N2 155.1(2) . . ?
O4 Fe1 N3 91.03(16) . . ?
N1 Fe1 N3 78.3(2) . . ?
N2 Fe1 N3 76.9(2) . . ?
O4 Fe1 O3 165.14(15) . . ?
N1 Fe1 O3 86.0(2) . . ?
N2 Fe1 O3 85.4(2) . . ?
N3 Fe1 O3 74.1(2) . . ?
O4 Fe1 Cl1 104.88(7) . . ?
N1 Fe1 Cl1 101.70(17) . . ?
N2 Fe1 Cl1 101.60(18) . . ?
N3 Fe1 Cl1 164.08(17) . . ?
O3 Fe1 Cl1 89.97(14) . . ?
C1 N1 C5 118.7(6) . . ?
C1 N1 Fe1 124.9(5) . . ?
C5 N1 Fe1 115.3(4) . . ?
C10 N2 C6 118.9(6) . . ?
C10 N2 Fe1 115.0(5) . . ?
C6 N2 Fe1 126.0(5) . . ?
C11 N3 C12 114.4(5) . . ?
C11 N3 C14 103.7(5) . . ?
C12 N3 C14 105.4(5) . . ?
C11 N3 Fe1 106.7(4) . . ?
C12 N3 Fe1 109.9(4) . . ?
C14 N3 Fe1 116.9(4) . . ?
C12 O1 C15 103.7(5) . . ?
C11 O2 C16 105.2(5) . . ?
C13 O3 Fe1 115.9(4) . . ?
C13 O3 H3 106.5(18) . . ?
Fe1 O3 H3 132(2) . . ?
Fe1 O4 Fe1 180.0 3_676 . ?
N1 C1 C2 122.4(7) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 118.4(7) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 119.2(7) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C5 C4 C3 119.6(7) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 121.5(7) . . ?
N1 C5 C12 117.7(6) . . ?
C4 C5 C12 120.8(7) . . ?
C7 C6 N2 121.1(7) . . ?
C7 C6 H6 119.5 . . ?
N2 C6 H6 119.5 . . ?
C6 C7 C8 120.0(7) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 119.3(7) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 118.5(8) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
N2 C10 C9 122.3(7) . . ?
N2 C10 C11 117.0(6) . . ?
C9 C10 C11 120.7(7) . . ?
O2 C11 N3 105.3(5) . . ?
O2 C11 C10 112.0(5) . . ?
N3 C11 C10 108.6(5) . . ?
O2 C11 H11 110.3 . . ?
N3 C11 H11 110.3 . . ?
C10 C11 H11 110.3 . . ?
O1 C12 N3 105.4(5) . . ?
O1 C12 C5 108.8(6) . . ?
N3 C12 C5 111.4(6) . . ?
O1 C12 H12 110.4 . . ?
N3 C12 H12 110.4 . . ?
C5 C12 H12 110.4 . . ?
O3 C13 C14 108.5(5) . . ?
O3 C13 H13A 110.0 . . ?
C14 C13 H13A 110.0 . . ?
O3 C13 H13B 110.0 . . ?
C14 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
C15 C14 C13 114.7(6) . . ?
C15 C14 N3 102.1(5) . . ?
C13 C14 N3 111.6(6) . . ?
C15 C14 C16 111.5(6) . . ?
C13 C14 C16 113.1(6) . . ?
N3 C14 C16 102.7(5) . . ?
O1 C15 C14 103.1(5) . . ?
O1 C15 H15A 111.1 . . ?
C14 C15 H15A 111.1 . . ?
O1 C15 H15B 111.1 . . ?
C14 C15 H15B 111.1 . . ?
H15A C15 H15B 109.1 . . ?
O2 C16 C14 105.5(5) . . ?
O2 C16 H16A 110.6 . . ?
C14 C16 H16A 110.6 . . ?
O2 C16 H16B 110.6 . . ?
C14 C16 H16B 110.6 . . ?
H16A C16 H16B 108.8 . . ?
Cl2 Fe2 Cl3 111.63(9) . . ?
Cl2 Fe2 Cl4 106.55(8) . . ?
Cl3 Fe2 Cl4 108.55(9) . . ?
Cl2 Fe2 Cl5 111.91(9) . . ?
Cl3 Fe2 Cl5 106.85(9) . . ?
Cl4 Fe2 Cl5 111.37(9) . . ?
O5 C17 C18 111.5(7) . . ?
O5 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
O5 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 O5 H5A 109.5 . . ?

_refine_diff_density_max         1.740
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.197

####################################################################### 
# 
# 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 1989144'
loop_
_audit_author_name
_audit_author_address
'Ennio Zangrando'
;University of Trieste
Italy
;
_audit_update_record             
;
2020-03-09 deposited with the CCDC.	2020-03-25 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         'C32 H34 Cl2 Fe2 N6 O7, 2(Cl), 3(H2 O)'
_chemical_formula_sum            'C32 H40 Cl4 Fe2 N6 O10'
_chemical_formula_weight         922.20

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.8719(6)
_cell_length_b                   16.9617(8)
_cell_length_c                   9.4064(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.136(2)
_cell_angle_gamma                90
_cell_volume                     1851.81(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    4146
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      25.71

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_F_000             948
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.363
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    1.137
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20605
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_av_R_equivalents  0.0804
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.519
_diffrn_reflns_theta_max         26.388
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3781
_reflns_number_gt                3083
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_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)+(0.0332P)²+5.1614P] 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         3781
_refine_ls_number_parameters     259
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.1100
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.001

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
Fe Fe 0.40697(4) 0.41906(3) 0.51315(5) 0.01599(14) Uani 1 1 d . . . . .
Cl1 Cl 0.37827(8) 0.36745(5) 0.28452(9) 0.0238(2) Uani 1 1 d . . . . .
N1 N 0.5531(2) 0.35586(17) 0.6318(3) 0.0180(6) Uani 1 1 d . . . . .
N2 N 0.2594(2) 0.49412(18) 0.4989(3) 0.0209(6) Uani 1 1 d . . . . .
N3 N 0.3982(2) 0.44142(17) 0.7424(3) 0.0164(6) Uani 1 1 d . . . . .
O1 O 0.4946(2) 0.39142(15) 0.9665(2) 0.0214(5) Uani 1 1 d . . . . .
O2 O 0.3042(2) 0.51944(16) 0.8817(3) 0.0247(6) Uani 1 1 d . . . . .
O3 O 0.3011(2) 0.32541(15) 0.5689(3) 0.0206(6) Uani 1 1 d . . . . .
H3A H 0.261(4) 0.306(3) 0.511(5) 0.025 Uiso 1 1 d . U . . .
O4 O 0.500000 0.500000 0.500000 0.0212(8) Uani 1 2 d S . P . .
C1 C 0.6200(3) 0.3078(2) 0.5715(4) 0.0216(8) Uani 1 1 d . . . . .
H1 H 0.592734 0.291016 0.474049 0.026 Uiso 1 1 calc R U . . .
C2 C 0.7260(3) 0.2820(2) 0.6446(4) 0.0252(8) Uani 1 1 d . . . . .
H2 H 0.770741 0.247645 0.598906 0.030 Uiso 1 1 calc R U . . .
C3 C 0.7666(3) 0.3072(2) 0.7872(4) 0.0242(8) Uani 1 1 d . . . . .
H3 H 0.839780 0.290547 0.840546 0.029 Uiso 1 1 calc R U . . .
C4 C 0.6983(3) 0.3571(2) 0.8496(4) 0.0220(8) Uani 1 1 d . . . . .
H4 H 0.724237 0.375574 0.946290 0.026 Uiso 1 1 calc R U . . .
C5 C 0.5917(3) 0.3797(2) 0.7692(4) 0.0184(7) Uani 1 1 d . . . . .
C6 C 0.1772(3) 0.5059(2) 0.3784(4) 0.0255(8) Uani 1 1 d . . . . .
H6 H 0.180758 0.477147 0.292737 0.031 Uiso 1 1 calc R U . . .
C7 C 0.0884(3) 0.5582(2) 0.3754(5) 0.0310(9) Uani 1 1 d . . . . .
H7 H 0.031978 0.565900 0.288642 0.037 Uiso 1 1 calc R U . . .
C8 C 0.0820(3) 0.5996(3) 0.5000(5) 0.0330(10) Uani 1 1 d . . . . .
H8 H 0.021199 0.636070 0.499674 0.040 Uiso 1 1 calc R U . . .
C9 C 0.1652(3) 0.5875(2) 0.6255(5) 0.0278(8) Uani 1 1 d . . . . .
H9 H 0.161834 0.614667 0.712824 0.033 Uiso 1 1 calc R U . . .
C10 C 0.2537(3) 0.5346(2) 0.6204(4) 0.0210(8) Uani 1 1 d . . . . .
C11 C 0.3488(3) 0.5206(2) 0.7535(4) 0.0208(7) Uani 1 1 d . . . . .
H11 H 0.409827 0.561888 0.760595 0.025 Uiso 1 1 calc R U . . .
C12 C 0.5140(3) 0.4309(2) 0.8403(4) 0.0181(7) Uani 1 1 d . . . . .
H12 H 0.550787 0.483388 0.867177 0.022 Uiso 1 1 calc R U . . .
C13 C 0.2411(3) 0.3407(2) 0.6828(4) 0.0251(8) Uani 1 1 d . . . . .
H13A H 0.218026 0.290276 0.721484 0.030 Uiso 1 1 calc R U . . .
H13B H 0.170510 0.371584 0.644347 0.030 Uiso 1 1 calc R U . . .
C14 C 0.3193(3) 0.3865(2) 0.8034(4) 0.0198(7) Uani 1 1 d . . . . .
C15 C 0.4044(3) 0.3369(2) 0.9092(4) 0.0222(8) Uani 1 1 d . . . . .
H15A H 0.368715 0.315567 0.987282 0.027 Uiso 1 1 calc R U . . .
H15B H 0.433710 0.292591 0.858795 0.027 Uiso 1 1 calc R U . . .
C16 C 0.2515(3) 0.4432(2) 0.8845(4) 0.0252(8) Uani 1 1 d . . . . .
H16A H 0.169230 0.445137 0.834946 0.030 Uiso 1 1 calc R U . . .
H16B H 0.256750 0.425483 0.985996 0.030 Uiso 1 1 calc R U . . .
Cl2 Cl -0.00961(11) 0.17589(9) 0.62069(16) 0.0575(4) Uani 1 1 d . . . . .
O1W O 0.1241(3) 0.2497(2) 0.4069(3) 0.0498(9) Uani 1 1 d D . . . .
H12A H 0.081(4) 0.230(3) 0.455(5) 0.075 Uiso 1 1 d D U . . .
H11A H 0.086(4) 0.277(3) 0.342(5) 0.075 Uiso 1 1 d D U . . .
O2W O 0.000000 0.500000 0.000000 0.176(5) Uani 1 2 d DS U P . .
H20 H 0.065(7) 0.504(11) 0.057(16) 0.264 Uiso 1 1 d D 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
Fe O4 1.7825(5) . ?
Fe N1 2.143(3) . ?
Fe N2 2.147(3) . ?
Fe O3 2.158(3) . ?
Fe N3 2.214(3) . ?
Fe Cl1 2.2802(10) . ?
N1 C5 1.339(4) . ?
N1 C1 1.343(4) . ?
N2 C6 1.346(5) . ?
N2 C10 1.346(5) . ?
N3 C11 1.478(4) . ?
N3 C12 1.496(4) . ?
N3 C14 1.517(4) . ?
O1 C12 1.423(4) . ?
O1 C15 1.432(4) . ?
O2 C11 1.415(4) . ?
O2 C16 1.440(5) . ?
O3 C13 1.429(4) . ?
O3 H3A 0.72(4) . ?
C1 C2 1.373(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.394(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(5) . ?
C4 H4 0.9500 . ?
C5 C12 1.522(5) . ?
C6 C7 1.374(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.518(5) . ?
C11 H11 1.0000 . ?
C12 H12 1.0000 . ?
C13 C14 1.520(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.515(5) . ?
C14 C16 1.554(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
O1W H12A 0.824(19) . ?
O1W H11A 0.823(19) . ?
O2W H20 0.85(2) . ?
O2W H20 0.85(2) 3_565 ?

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
O4 Fe N1 88.61(8) . . ?
O4 Fe N2 92.78(8) . . ?
N1 Fe N2 152.86(11) . . ?
O4 Fe O3 170.07(7) . . ?
N1 Fe O3 87.39(11) . . ?
N2 Fe O3 86.69(11) . . ?
O4 Fe N3 95.31(8) . . ?
N1 Fe N3 77.12(11) . . ?
N2 Fe N3 75.77(11) . . ?
O3 Fe N3 74.94(10) . . ?
O4 Fe Cl1 101.66(3) . . ?
N1 Fe Cl1 104.09(8) . . ?
N2 Fe Cl1 102.16(9) . . ?
O3 Fe Cl1 88.13(7) . . ?
N3 Fe Cl1 163.00(8) . . ?
C5 N1 C1 118.5(3) . . ?
C5 N1 Fe 115.3(2) . . ?
C1 N1 Fe 124.7(2) . . ?
C6 N2 C10 118.9(3) . . ?
C6 N2 Fe 125.3(3) . . ?
C10 N2 Fe 115.8(2) . . ?
C11 N3 C12 113.1(3) . . ?
C11 N3 C14 104.3(3) . . ?
C12 N3 C14 104.8(3) . . ?
C11 N3 Fe 109.0(2) . . ?
C12 N3 Fe 110.7(2) . . ?
C14 N3 Fe 115.0(2) . . ?
C12 O1 C15 103.3(2) . . ?
C11 O2 C16 105.7(3) . . ?
C13 O3 Fe 117.2(2) . . ?
C13 O3 H3A 107(4) . . ?
Fe O3 H3A 119(4) . . ?
Fe O4 Fe 180.0 3_666 . ?
N1 C1 C2 122.9(3) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 C2 C3 118.6(3) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 118.7(3) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 122.1(3) . . ?
N1 C5 C12 118.7(3) . . ?
C4 C5 C12 119.2(3) . . ?
N2 C6 C7 122.0(4) . . ?
N2 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C6 C7 C8 119.3(4) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C7 C8 C9 119.4(4) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C8 C9 C10 118.3(4) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
N2 C10 C9 122.1(3) . . ?
N2 C10 C11 117.3(3) . . ?
C9 C10 C11 120.6(3) . . ?
O2 C11 N3 105.8(3) . . ?
O2 C11 C10 111.0(3) . . ?
N3 C11 C10 108.7(3) . . ?
O2 C11 H11 110.4 . . ?
N3 C11 H11 110.4 . . ?
C10 C11 H11 110.4 . . ?
O1 C12 N3 106.3(3) . . ?
O1 C12 C5 108.5(3) . . ?
N3 C12 C5 111.2(3) . . ?
O1 C12 H12 110.3 . . ?
N3 C12 H12 110.3 . . ?
C5 C12 H12 110.3 . . ?
O3 C13 C14 109.2(3) . . ?
O3 C13 H13A 109.8 . . ?
C14 C13 H13A 109.8 . . ?
O3 C13 H13B 109.8 . . ?
C14 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
C15 C14 N3 102.1(3) . . ?
C15 C14 C13 115.2(3) . . ?
N3 C14 C13 111.1(3) . . ?
C15 C14 C16 111.4(3) . . ?
N3 C14 C16 103.3(3) . . ?
C13 C14 C16 112.6(3) . . ?
O1 C15 C14 103.4(3) . . ?
O1 C15 H15A 111.1 . . ?
C14 C15 H15A 111.1 . . ?
O1 C15 H15B 111.1 . . ?
C14 C15 H15B 111.1 . . ?
H15A C15 H15B 109.1 . . ?
O2 C16 C14 106.0(3) . . ?
O2 C16 H16A 110.5 . . ?
C14 C16 H16A 110.5 . . ?
O2 C16 H16B 110.5 . . ?
C14 C16 H16B 110.5 . . ?
H16A C16 H16B 108.7 . . ?
H12A O1W H11A 109(3) . . ?
H20 O2W H20 180.00(2) . 3_565 ?

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
C5 N1 C1 C2 0.1(5) . . . . ?
Fe N1 C1 C2 165.4(3) . . . . ?
N1 C1 C2 C3 -0.6(6) . . . . ?
C1 C2 C3 C4 0.2(6) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C1 N1 C5 C4 0.8(5) . . . . ?
Fe N1 C5 C4 -165.9(3) . . . . ?
C1 N1 C5 C12 -177.2(3) . . . . ?
Fe N1 C5 C12 16.2(4) . . . . ?
C3 C4 C5 N1 -1.1(5) . . . . ?
C3 C4 C5 C12 176.8(3) . . . . ?
C10 N2 C6 C7 0.4(6) . . . . ?
Fe N2 C6 C7 -176.4(3) . . . . ?
N2 C6 C7 C8 -0.7(6) . . . . ?
C6 C7 C8 C9 -0.1(6) . . . . ?
C7 C8 C9 C10 1.0(6) . . . . ?
C6 N2 C10 C9 0.6(5) . . . . ?
Fe N2 C10 C9 177.7(3) . . . . ?
C6 N2 C10 C11 -179.1(3) . . . . ?
Fe N2 C10 C11 -2.1(4) . . . . ?
C8 C9 C10 N2 -1.3(6) . . . . ?
C8 C9 C10 C11 178.4(3) . . . . ?
C16 O2 C11 N3 -40.1(3) . . . . ?
C16 O2 C11 C10 77.7(3) . . . . ?
C12 N3 C11 O2 -78.8(3) . . . . ?
C14 N3 C11 O2 34.4(3) . . . . ?
Fe N3 C11 O2 157.7(2) . . . . ?
C12 N3 C11 C10 161.9(3) . . . . ?
C14 N3 C11 C10 -84.9(3) . . . . ?
Fe N3 C11 C10 38.4(3) . . . . ?
N2 C10 C11 O2 -141.1(3) . . . . ?
C9 C10 C11 O2 39.1(5) . . . . ?
N2 C10 C11 N3 -25.1(4) . . . . ?
C9 C10 C11 N3 155.1(3) . . . . ?
C15 O1 C12 N3 37.9(3) . . . . ?
C15 O1 C12 C5 -81.8(3) . . . . ?
C11 N3 C12 O1 98.0(3) . . . . ?
C14 N3 C12 O1 -14.9(3) . . . . ?
Fe N3 C12 O1 -139.4(2) . . . . ?
C11 N3 C12 C5 -144.1(3) . . . . ?
C14 N3 C12 C5 103.0(3) . . . . ?
Fe N3 C12 C5 -21.5(3) . . . . ?
N1 C5 C12 O1 121.0(3) . . . . ?
C4 C5 C12 O1 -57.0(4) . . . . ?
N1 C5 C12 N3 4.4(4) . . . . ?
C4 C5 C12 N3 -173.6(3) . . . . ?
Fe O3 C13 C14 -40.3(4) . . . . ?
C11 N3 C14 C15 -131.4(3) . . . . ?
C12 N3 C14 C15 -12.3(3) . . . . ?
Fe N3 C14 C15 109.4(2) . . . . ?
C11 N3 C14 C13 105.3(3) . . . . ?
C12 N3 C14 C13 -135.7(3) . . . . ?
Fe N3 C14 C13 -13.9(4) . . . . ?
C11 N3 C14 C16 -15.7(3) . . . . ?
C12 N3 C14 C16 103.4(3) . . . . ?
Fe N3 C14 C16 -134.9(2) . . . . ?
O3 C13 C14 C15 -82.1(4) . . . . ?
O3 C13 C14 N3 33.4(4) . . . . ?
O3 C13 C14 C16 148.7(3) . . . . ?
C12 O1 C15 C14 -45.8(3) . . . . ?
N3 C14 C15 O1 35.4(3) . . . . ?
C13 C14 C15 O1 155.9(3) . . . . ?
C16 C14 C15 O1 -74.3(3) . . . . ?
C11 O2 C16 C14 29.0(3) . . . . ?
C15 C14 C16 O2 101.5(3) . . . . ?
N3 C14 C16 O2 -7.4(3) . . . . ?
C13 C14 C16 O2 -127.4(3) . . . . ?

_refine_diff_density_max         0.838
_refine_diff_density_min         -0.713
_refine_diff_density_rms         0.092

