# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_fe3
_database_code_depnum_ccdc_archive 'CCDC 1903068'
loop_
_audit_author_name
_audit_author_address
'Vladimir Lazarenko'
;NRC Kurchatov institute
Russia
;
_audit_update_record             
;
2019-03-13 deposited with the CCDC.	2019-05-21 downloaded from the CCDC.
;
_audit_creation_date             2019-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 Fe N6 O4, 3(H2 O)'
_chemical_formula_sum            'C16 H21 Fe N6 O7'
_chemical_formula_weight         465.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0050 0.0020 '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 0.3560 1.0610 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0090 0.0040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0150 0.0080 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.587(4)
_cell_length_b                   12.556(3)
_cell_length_c                   9.0534(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.77(3)
_cell_angle_gamma                90
_cell_volume                     1994.8(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    700
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      2.25
_cell_measurement_theta_min      30.8
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.877
_exptl_absorpt_coefficient_mu    1.128
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scala (Evans, 2006)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             964
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            21114
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        28.782
_diffrn_reflns_theta_max         30.853
_diffrn_reflns_theta_min         2.252
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       /f
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.80246
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3812
_reflns_number_total             4319
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.885
_refine_diff_density_min         -0.915
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       0.031(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4319
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0631
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1205P)²+1.0317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1678
_refine_ls_wR_factor_ref         0.1751
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 H5A-O5
 0.84 with sigma of 0.02
 H5B-O5
 0.84 with sigma of 0.02
 H6C_$3-O6_$3
 0.84 with sigma of 0.02
 H6D_$3-O6_$3
 0.84 with sigma of 0.02
 H6C-O6
 0.84 with sigma of 0.02
 H6D-O6
 0.84 with sigma of 0.02
 H7A-O7
 0.84 with sigma of 0.02
 H7B-O7
 0.84 with sigma of 0.02
 N6-H6B \\sim N6-H6A
 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
  C14(H14)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.27752(2) 0.49225(3) 0.67012(4) 0.0248(2) Uani 1 1 d . . . . .
O1 O 0.18658(14) 0.48657(16) 0.5473(2) 0.0317(5) Uani 1 1 d . . . . .
O2 O 0.22909(13) 0.50570(15) 0.8553(3) 0.0290(5) Uani 1 1 d . . . . .
O3 O 0.37239(12) 0.44653(15) 0.7940(2) 0.0290(4) Uani 1 1 d . . . . .
O4 O 0.35239(13) 0.53865(16) 0.5092(2) 0.0306(5) Uani 1 1 d . . . . .
N1 N 0.28392(14) 0.66182(19) 0.6811(2) 0.0258(5) Uani 1 1 d . . . . .
N2 N 0.33366(15) 0.7068(2) 0.5870(3) 0.0274(5) Uani 1 1 d . . . . .
H2 H 0.336(2) 0.771(3) 0.582(4) 0.033 Uiso 1 1 d R . . . .
N3 N 0.41705(17) 0.6747(2) 0.4084(3) 0.0329(6) Uani 1 1 d . . . . .
H3A H 0.439(2) 0.630(3) 0.361(4) 0.040 Uiso 1 1 d R . . . .
H3B H 0.429(2) 0.738(3) 0.407(4) 0.040 Uiso 1 1 d R . . . .
N4 N 0.29335(14) 0.33110(19) 0.6131(2) 0.0260(5) Uani 1 1 d . . . . .
N5 N 0.35719(15) 0.28151(18) 0.6825(3) 0.0291(5) Uani 1 1 d . . . . .
N6 N 0.46265(16) 0.3192(2) 0.8396(3) 0.0336(6) Uani 1 1 d D . . . .
H6A H 0.472(2) 0.251(2) 0.841(4) 0.040 Uiso 1 1 d DR . . . .
H6B H 0.477(2) 0.354(3) 0.920(4) 0.040 Uiso 1 1 d DR . . . .
C1 C 0.15343(17) 0.4154(2) 0.4568(3) 0.0276(6) Uani 1 1 d . . . . .
C2 C 0.08432(18) 0.4419(2) 0.3777(3) 0.0311(6) Uani 1 1 d . . . . .
H2A H 0.061647 0.509353 0.393278 0.037 Uiso 1 1 calc R . . . .
C3 C 0.04902(18) 0.3715(2) 0.2780(3) 0.0315(6) Uani 1 1 d . . . . .
H3 H 0.003038 0.391569 0.224294 0.038 Uiso 1 1 calc R . . . .
C4 C 0.08033(18) 0.2709(2) 0.2554(3) 0.0318(6) Uani 1 1 d . . . . .
H4 H 0.056429 0.223204 0.185314 0.038 Uiso 1 1 calc R . . . .
C5 C 0.14619(18) 0.2416(2) 0.3360(3) 0.0306(6) Uani 1 1 d . . . . .
H5 H 0.166346 0.172282 0.323189 0.037 Uiso 1 1 calc R . . . .
C6 C 0.18446(17) 0.3120(2) 0.4369(3) 0.0266(6) Uani 1 1 d . . . . .
C7 C 0.25259(17) 0.2750(2) 0.5183(3) 0.0279(6) Uani 1 1 d . . . . .
H7 H 0.268653 0.204083 0.500865 0.034 Uiso 1 1 calc R . . . .
C8 C 0.18140(17) 0.5801(2) 0.8983(3) 0.0271(6) Uani 1 1 d . . . . .
C9 C 0.12720(19) 0.5526(3) 0.9986(3) 0.0325(6) Uani 1 1 d . . . . .
H9 H 0.123041 0.480882 1.030315 0.039 Uiso 1 1 calc R . . . .
C10 C 0.07945(19) 0.6302(3) 1.0519(3) 0.0348(7) Uani 1 1 d . . . . .
H10 H 0.041931 0.610431 1.117614 0.042 Uiso 1 1 calc R . . . .
C11 C 0.08601(19) 0.7366(3) 1.0100(3) 0.0349(7) Uani 1 1 d . . . . .
H11 H 0.054007 0.789291 1.048753 0.042 Uiso 1 1 calc R . . . .
C12 C 0.13932(18) 0.7647(2) 0.9120(3) 0.0313(6) Uani 1 1 d . . . . .
H12 H 0.144034 0.837176 0.883907 0.038 Uiso 1 1 calc R . . . .
C13 C 0.18678(17) 0.6878(2) 0.8530(3) 0.0281(6) Uani 1 1 d . . . . .
C14 C 0.24080(17) 0.7249(2) 0.7505(3) 0.0274(6) Uani 1 1 d . . . . .
H14 H 0.244640 0.799324 0.733683 0.033 Uiso 1 1 calc R . . . .
C15 C 0.36805(17) 0.6373(2) 0.5009(3) 0.0261(6) Uani 1 1 d . . . . .
C16 C 0.39488(17) 0.3501(2) 0.7717(3) 0.0277(6) Uani 1 1 d . . . . .
O5 O 0.33862(15) 0.92207(17) 0.5745(2) 0.0369(5) Uani 1 1 d D . . . .
H5A H 0.360(2) 0.969(3) 0.633(4) 0.055 Uiso 1 1 d DR . . . .
H5B H 0.314(2) 0.954(3) 0.502(4) 0.055 Uiso 1 1 d DR . . . .
O6 O 0.39430(14) 0.07825(16) 0.7655(2) 0.0334(5) Uani 1 1 d D . . . .
H6C H 0.373(2) 0.137(2) 0.736(4) 0.050 Uiso 1 1 d DR . . . .
H6D H 0.375(2) 0.059(3) 0.844(3) 0.050 Uiso 1 1 d DR . . . .
O7 O 0.52858(14) 0.11251(18) 0.6334(3) 0.0360(5) Uani 1 1 d D . . . .
H7A H 0.4931(19) 0.096(4) 0.689(4) 0.054 Uiso 1 1 d DR . . . .
H7B H 0.559(2) 0.060(3) 0.651(5) 0.054 Uiso 1 1 d DR . . . .


_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 1.889(2) . ?
Fe1 O2 1.937(2) . ?
Fe1 O3 2.031(2) . ?
Fe1 O4 2.109(2) . ?
Fe1 N1 2.134(2) . ?
Fe1 N4 2.111(2) . ?
O1 C1 1.322(3) . ?
O2 C8 1.331(3) . ?
O3 C16 1.294(3) . ?
O4 C15 1.272(3) . ?
N1 N2 1.381(3) . ?
N1 C14 1.288(4) . ?
N2 H2 0.81(4) . ?
N2 C15 1.340(4) . ?
N3 H3A 0.82(4) . ?
N3 H3B 0.82(4) . ?
N3 C15 1.327(4) . ?
N4 N5 1.397(3) . ?
N4 C7 1.291(4) . ?
N5 C16 1.327(4) . ?
N6 H6A 0.87(3) . ?
N6 H6B 0.87(3) . ?
N6 C16 1.361(4) . ?
C1 C2 1.409(4) . ?
C1 C6 1.424(4) . ?
C2 H2A 0.9500 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.410(4) . ?
C6 C7 1.442(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.402(4) . ?
C8 C13 1.417(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.393(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.396(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.405(4) . ?
C13 C14 1.448(4) . ?
C14 H14 0.9500 . ?
O5 H5A 0.864(19) . ?
O5 H5B 0.858(19) . ?
O6 H6C 0.854(14) . ?
O6 H6D 0.845(14) . ?
O7 H7A 0.854(19) . ?
O7 H7B 0.857(19) . ?

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 96.28(10) . . ?
O1 Fe1 O3 161.39(8) . . ?
O1 Fe1 O4 98.43(10) . . ?
O1 Fe1 N1 96.04(9) . . ?
O1 Fe1 N4 86.55(9) . . ?
O2 Fe1 O3 86.49(9) . . ?
O2 Fe1 O4 154.67(9) . . ?
O2 Fe1 N1 84.12(8) . . ?
O2 Fe1 N4 111.59(9) . . ?
O3 Fe1 O4 86.10(9) . . ?
O3 Fe1 N1 102.56(9) . . ?
O3 Fe1 N4 75.38(9) . . ?
O4 Fe1 N1 73.94(8) . . ?
O4 Fe1 N4 89.84(9) . . ?
N4 Fe1 N1 163.78(9) . . ?
C1 O1 Fe1 135.43(19) . . ?
C8 O2 Fe1 129.48(18) . . ?
C16 O3 Fe1 115.26(18) . . ?
C15 O4 Fe1 117.18(18) . . ?
N2 N1 Fe1 114.37(17) . . ?
C14 N1 Fe1 127.24(19) . . ?
C14 N1 N2 117.8(2) . . ?
N1 N2 H2 118(3) . . ?
C15 N2 N1 114.9(2) . . ?
C15 N2 H2 127(3) . . ?
H3A N3 H3B 122(4) . . ?
C15 N3 H3A 116(3) . . ?
C15 N3 H3B 122(3) . . ?
N5 N4 Fe1 115.59(17) . . ?
C7 N4 Fe1 127.6(2) . . ?
C7 N4 N5 116.8(2) . . ?
C16 N5 N4 109.8(2) . . ?
H6A N6 H6B 115(4) . . ?
C16 N6 H6A 117(3) . . ?
C16 N6 H6B 116(3) . . ?
O1 C1 C2 119.0(3) . . ?
O1 C1 C6 122.5(3) . . ?
C2 C1 C6 118.5(3) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 H2A 119.5 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.7(3) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C7 122.8(3) . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 C7 118.3(3) . . ?
N4 C7 C6 124.8(3) . . ?
N4 C7 H7 117.6 . . ?
C6 C7 H7 117.6 . . ?
O2 C8 C9 119.0(3) . . ?
O2 C8 C13 122.0(3) . . ?
C9 C8 C13 118.9(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(3) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C8 C13 C14 123.4(3) . . ?
C12 C13 C8 119.6(3) . . ?
C12 C13 C14 117.0(3) . . ?
N1 C14 C13 123.1(3) . . ?
N1 C14 H14 118.4 . . ?
C13 C14 H14 118.4 . . ?
O4 C15 N2 119.5(3) . . ?
O4 C15 N3 122.3(3) . . ?
N3 C15 N2 118.3(3) . . ?
O3 C16 N5 123.8(3) . . ?
O3 C16 N6 117.6(3) . . ?
N5 C16 N6 118.5(3) . . ?
H5A O5 H5B 109(4) . . ?
H6C O6 H6D 108(4) . . ?
H7A O7 H7B 100(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O5 0.81(4) 1.90(4) 2.707(3) 179(4) . yes
N3 H3B O7 0.82(4) 2.07(4) 2.871(4) 168(4) 3_666 yes
N6 H6B O7 0.87(3) 2.12(3) 2.957(4) 161(4) 4_566 yes
O5 H5A O6 0.864(19) 1.89(2) 2.752(3) 173(5) 1_565 yes
O5 H5B O2 0.858(19) 2.00(2) 2.823(3) 160(4) 4_575 yes
O6 H6C N5 0.854(14) 1.899(18) 2.727(3) 163(4) . yes
O7 H7A O6 0.854(19) 1.92(2) 2.751(3) 162(4) . yes
O7 H7B O3 0.857(19) 1.91(2) 2.767(3) 175(4) 2_646 yes

_olex2_submission_special_instructions 'No special instructions were received'
