# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_mil37
_database_code_depnum_ccdc_archive 'CCDC 1996849'
loop_
_audit_author_name
_audit_author_address
'Kamil Ivshin'
;Arbuzov Institute of Organic and Physical Chemistry
Russia
;
_audit_update_record             
;
2020-11-05 deposited with the CCDC.	2020-12-08 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         ' C14 H20 Fe N O2 P, H2 O'
_chemical_formula_sum            'C14 H22 Fe N O3 P'
_chemical_formula_weight         339.14

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'
P P 0.1023 0.0942 '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                   16.210(8)
_cell_length_b                   7.525(4)
_cell_length_c                   12.606(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.855(6)
_cell_angle_gamma                90
_cell_volume                     1523.3(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1128
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      19.63

_exptl_crystal_description       prizm
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.052
_exptl_absorpt_coefficient_mu    1.101
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7765
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS Smart Apex'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13163
_diffrn_reflns_av_unetI/netI     0.1041
_diffrn_reflns_av_R_equivalents  0.0922
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.537
_diffrn_reflns_theta_max         28.325
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3732
_reflns_number_gt                1762
_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 APEX3'
_computing_cell_refinement       'APEX3 v2018.7-2'
_computing_data_reduction        'SAINT NT v6.0 (Bruker AXS, 2003)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury 2020.1'
_computing_publication_material  'enCIFer 2020.1'
_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)+(0.0647P)²] 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         3732
_refine_ls_number_parameters     200
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.1418
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1678
_refine_ls_wR_factor_gt          0.1306
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.096
_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 0.14062(4) 0.40689(9) 0.67108(5) 0.0441(3) Uani 1 1 d . . . . .
P1 P 0.32778(7) 0.38401(18) 0.56771(10) 0.0430(3) Uani 1 1 d . . . . .
O2 O 0.40370(19) 0.4861(5) 0.6097(3) 0.0619(10) Uani 1 1 d . . . . .
O1 O 0.3123(2) 0.3462(5) 0.4520(3) 0.0638(10) Uani 1 1 d . . . . .
N13 N 0.3781(2) 0.6689(5) 0.7833(3) 0.0477(10) Uani 1 1 d . . . . .
H13 H 0.393(3) 0.619(6) 0.722(4) 0.051(15) Uiso 1 1 d . . . . .
O1W O 0.5382(3) 0.7181(6) 0.6312(4) 0.0729(11) Uani 1 1 d D . . . .
H1WA H 0.581(3) 0.684(9) 0.605(5) 0.11(3) Uiso 1 1 d D . . . .
H1WB H 0.500(3) 0.645(6) 0.608(5) 0.10(3) Uiso 1 1 d D . . . .
C10 C 0.2368(3) 0.5754(5) 0.7126(4) 0.0382(11) Uani 1 1 d . . . . .
C11 C 0.3036(3) 0.5630(6) 0.8076(4) 0.0443(12) Uani 1 1 d . . . . .
H11 H 0.320724 0.438250 0.815462 0.053 Uiso 1 1 calc R U . . .
C6 C 0.2415(3) 0.4999(6) 0.6087(4) 0.0392(11) Uani 1 1 d . . . . .
C7 C 0.1666(3) 0.5464(6) 0.5421(4) 0.0498(13) Uani 1 1 d . . . . .
H7 H 0.152263 0.514953 0.470587 0.060 Uiso 1 1 calc R U . . .
C9 C 0.1605(3) 0.6673(6) 0.7069(4) 0.0540(13) Uani 1 1 d . . . . .
H9 H 0.141846 0.729830 0.762651 0.065 Uiso 1 1 calc R U . . .
C8 C 0.1178(3) 0.6485(7) 0.6037(5) 0.0610(15) Uani 1 1 d . . . . .
H8 H 0.065650 0.695693 0.579491 0.073 Uiso 1 1 calc R U . . .
C15 C 0.4500(3) 0.6567(8) 0.8688(4) 0.0729(18) Uani 1 1 d . . . . .
H15A H 0.439166 0.726423 0.929222 0.109 Uiso 1 1 calc R U . . .
H15B H 0.498890 0.700930 0.842528 0.109 Uiso 1 1 calc R U . . .
H15C H 0.458501 0.534969 0.890233 0.109 Uiso 1 1 calc R U . . .
C12 C 0.2751(4) 0.6204(8) 0.9115(4) 0.0737(18) Uani 1 1 d . . . . .
H12A H 0.319335 0.602261 0.969395 0.111 Uiso 1 1 calc R U . . .
H12B H 0.227513 0.551525 0.923820 0.111 Uiso 1 1 calc R U . . .
H12C H 0.260436 0.744076 0.907378 0.111 Uiso 1 1 calc R U . . .
C14 C 0.3592(4) 0.8553(6) 0.7508(5) 0.0721(17) Uani 1 1 d . . . . .
H14A H 0.315939 0.857178 0.690738 0.108 Uiso 1 1 calc R U . . .
H14B H 0.408394 0.910341 0.731224 0.108 Uiso 1 1 calc R U . . .
H14C H 0.341201 0.919062 0.809484 0.108 Uiso 1 1 calc R U . . .
C4 C 0.0765(4) 0.3069(9) 0.7823(6) 0.092(2) Uani 1 1 d D U . . .
H4 H 0.063586 0.369424 0.841452 0.111 Uiso 1 1 calc R U . . .
C2 C 0.0702(5) 0.1942(9) 0.6180(6) 0.087(2) Uani 1 1 d . U . . .
H2 H 0.051087 0.166396 0.546942 0.105 Uiso 1 1 calc R U . . .
C3 C 0.0300(4) 0.2940(10) 0.6824(6) 0.090(2) Uani 1 1 d D U . . .
H3 H -0.021709 0.346897 0.662740 0.109 Uiso 1 1 calc R U . . .
C5 C 0.1475(4) 0.2048(8) 0.7746(5) 0.0826(18) Uani 1 1 d D U . . .
H5 H 0.190653 0.184344 0.829793 0.099 Uiso 1 1 calc R U . . .
C1 C 0.1432(4) 0.1405(8) 0.6737(6) 0.084(2) Uani 1 1 d . U . . .
H1A H 0.183471 0.071450 0.647332 0.101 Uiso 1 1 calc R U . . .
H1 H 0.332(2) 0.235(5) 0.620(3) 0.039(11) 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 C5 1.997(5) . ?
Fe1 C4 2.002(6) . ?
Fe1 C1 2.006(6) . ?
Fe1 C3 2.007(6) . ?
Fe1 C8 2.019(5) . ?
Fe1 C10 2.023(4) . ?
Fe1 C2 2.027(6) . ?
Fe1 C9 2.027(5) . ?
Fe1 C7 2.027(5) . ?
Fe1 C6 2.034(4) . ?
P1 O1 1.473(4) . ?
P1 O2 1.485(3) . ?
P1 C6 1.783(4) . ?
P1 H1 1.30(4) . ?
N13 C15 1.478(6) . ?
N13 C14 1.481(6) . ?
N13 C11 1.512(6) . ?
N13 H13 0.92(5) . ?
O1W H1WA 0.848(10) . ?
O1W H1WB 0.848(10) . ?
C10 C9 1.410(6) . ?
C10 C6 1.439(6) . ?
C10 C11 1.504(6) . ?
C11 C12 1.510(6) . ?
C11 H11 0.9800 . ?
C6 C7 1.424(6) . ?
C7 C8 1.409(7) . ?
C7 H7 0.9300 . ?
C9 C8 1.395(7) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C4 C3 1.380(8) . ?
C4 C5 1.398(8) . ?
C4 H4 0.9300 . ?
C2 C3 1.339(8) . ?
C2 C1 1.354(8) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C5 C1 1.353(8) . ?
C5 H5 0.9300 . ?
C1 H1A 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
C5 Fe1 C4 40.9(2) . . ?
C5 Fe1 C1 39.5(2) . . ?
C4 Fe1 C1 67.9(3) . . ?
C5 Fe1 C3 66.5(3) . . ?
C4 Fe1 C3 40.3(2) . . ?
C1 Fe1 C3 66.0(3) . . ?
C5 Fe1 C8 162.0(3) . . ?
C4 Fe1 C8 123.4(3) . . ?
C1 Fe1 C8 155.4(3) . . ?
C3 Fe1 C8 107.3(3) . . ?
C5 Fe1 C10 109.7(2) . . ?
C4 Fe1 C10 120.7(3) . . ?
C1 Fe1 C10 127.5(2) . . ?
C3 Fe1 C10 155.8(3) . . ?
C8 Fe1 C10 68.6(2) . . ?
C5 Fe1 C2 66.0(3) . . ?
C4 Fe1 C2 67.1(3) . . ?
C1 Fe1 C2 39.2(2) . . ?
C3 Fe1 C2 38.8(2) . . ?
C8 Fe1 C2 120.7(3) . . ?
C10 Fe1 C2 163.9(3) . . ?
C5 Fe1 C9 126.7(3) . . ?
C4 Fe1 C9 106.8(3) . . ?
C1 Fe1 C9 163.8(3) . . ?
C3 Fe1 C9 120.7(3) . . ?
C8 Fe1 C9 40.3(2) . . ?
C10 Fe1 C9 40.75(18) . . ?
C2 Fe1 C9 154.5(3) . . ?
C5 Fe1 C7 156.8(3) . . ?
C4 Fe1 C7 160.1(3) . . ?
C1 Fe1 C7 121.6(3) . . ?
C3 Fe1 C7 124.2(2) . . ?
C8 Fe1 C7 40.7(2) . . ?
C10 Fe1 C7 69.26(19) . . ?
C2 Fe1 C7 108.3(3) . . ?
C9 Fe1 C7 68.5(2) . . ?
C5 Fe1 C6 122.6(2) . . ?
C4 Fe1 C6 157.2(3) . . ?
C1 Fe1 C6 109.5(2) . . ?
C3 Fe1 C6 161.3(3) . . ?
C8 Fe1 C6 68.78(19) . . ?
C10 Fe1 C6 41.55(17) . . ?
C2 Fe1 C6 126.2(3) . . ?
C9 Fe1 C6 68.98(19) . . ?
C7 Fe1 C6 41.05(17) . . ?
O1 P1 O2 118.3(2) . . ?
O1 P1 C6 110.3(2) . . ?
O2 P1 C6 106.7(2) . . ?
O1 P1 H1 109.1(16) . . ?
O2 P1 H1 106.4(16) . . ?
C6 P1 H1 105.2(16) . . ?
C15 N13 C14 111.9(4) . . ?
C15 N13 C11 113.0(4) . . ?
C14 N13 C11 114.5(4) . . ?
C15 N13 H13 108(3) . . ?
C14 N13 H13 103(3) . . ?
C11 N13 H13 105(3) . . ?
H1WA O1W H1WB 105(6) . . ?
C9 C10 C6 107.6(4) . . ?
C9 C10 C11 127.0(4) . . ?
C6 C10 C11 125.3(4) . . ?
C9 C10 Fe1 69.8(3) . . ?
C6 C10 Fe1 69.6(3) . . ?
C11 C10 Fe1 127.8(3) . . ?
C10 C11 C12 113.6(4) . . ?
C10 C11 N13 108.3(4) . . ?
C12 C11 N13 111.8(4) . . ?
C10 C11 H11 107.6 . . ?
C12 C11 H11 107.6 . . ?
N13 C11 H11 107.6 . . ?
C7 C6 C10 107.0(4) . . ?
C7 C6 P1 126.1(4) . . ?
C10 C6 P1 126.7(3) . . ?
C7 C6 Fe1 69.2(3) . . ?
C10 C6 Fe1 68.8(2) . . ?
P1 C6 Fe1 130.4(2) . . ?
C8 C7 C6 107.8(5) . . ?
C8 C7 Fe1 69.3(3) . . ?
C6 C7 Fe1 69.7(3) . . ?
C8 C7 H7 126.1 . . ?
C6 C7 H7 126.1 . . ?
Fe1 C7 H7 126.5 . . ?
C8 C9 C10 108.5(4) . . ?
C8 C9 Fe1 69.5(3) . . ?
C10 C9 Fe1 69.5(3) . . ?
C8 C9 H9 125.7 . . ?
C10 C9 H9 125.7 . . ?
Fe1 C9 H9 126.8 . . ?
C9 C8 C7 109.0(4) . . ?
C9 C8 Fe1 70.1(3) . . ?
C7 C8 Fe1 69.9(3) . . ?
C9 C8 H8 125.5 . . ?
C7 C8 H8 125.5 . . ?
Fe1 C8 H8 126.0 . . ?
N13 C15 H15A 109.5 . . ?
N13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N13 C14 H14A 109.5 . . ?
N13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C4 C5 104.5(6) . . ?
C3 C4 Fe1 70.1(4) . . ?
C5 C4 Fe1 69.3(3) . . ?
C3 C4 H4 127.7 . . ?
C5 C4 H4 127.7 . . ?
Fe1 C4 H4 124.5 . . ?
C3 C2 C1 108.4(7) . . ?
C3 C2 Fe1 69.8(4) . . ?
C1 C2 Fe1 69.5(4) . . ?
C3 C2 H2 125.8 . . ?
C1 C2 H2 125.8 . . ?
Fe1 C2 H2 126.4 . . ?
C2 C3 C4 110.0(7) . . ?
C2 C3 Fe1 71.4(4) . . ?
C4 C3 Fe1 69.7(4) . . ?
C2 C3 H3 125.0 . . ?
C4 C3 H3 125.0 . . ?
Fe1 C3 H3 125.5 . . ?
C1 C5 C4 109.0(6) . . ?
C1 C5 Fe1 70.6(4) . . ?
C4 C5 Fe1 69.7(3) . . ?
C1 C5 H5 125.5 . . ?
C4 C5 H5 125.5 . . ?
Fe1 C5 H5 125.7 . . ?
C5 C1 C2 108.0(7) . . ?
C5 C1 Fe1 69.9(4) . . ?
C2 C1 Fe1 71.2(4) . . ?
C5 C1 H1A 126.0 . . ?
C2 C1 H1A 126.0 . . ?
Fe1 C1 H1A 124.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C10 C11 C12 14.7(7) . . . . ?
C6 C10 C11 C12 -168.0(4) . . . . ?
Fe1 C10 C11 C12 -77.4(5) . . . . ?
C9 C10 C11 N13 -110.2(5) . . . . ?
C6 C10 C11 N13 67.2(5) . . . . ?
Fe1 C10 C11 N13 157.8(3) . . . . ?
C15 N13 C11 C10 -176.3(4) . . . . ?
C14 N13 C11 C10 54.0(5) . . . . ?
C15 N13 C11 C12 57.8(6) . . . . ?
C14 N13 C11 C12 -72.0(6) . . . . ?
C9 C10 C6 C7 -0.8(5) . . . . ?
C11 C10 C6 C7 -178.5(4) . . . . ?
Fe1 C10 C6 C7 58.9(3) . . . . ?
C9 C10 C6 P1 175.0(3) . . . . ?
C11 C10 C6 P1 -2.7(7) . . . . ?
Fe1 C10 C6 P1 -125.3(4) . . . . ?
C9 C10 C6 Fe1 -59.7(3) . . . . ?
C11 C10 C6 Fe1 122.6(4) . . . . ?
O1 P1 C6 C7 1.8(5) . . . . ?
O2 P1 C6 C7 131.5(4) . . . . ?
O1 P1 C6 C10 -173.2(4) . . . . ?
O2 P1 C6 C10 -43.6(4) . . . . ?
O1 P1 C6 Fe1 94.3(3) . . . . ?
O2 P1 C6 Fe1 -136.0(3) . . . . ?
C10 C6 C7 C8 0.4(5) . . . . ?
P1 C6 C7 C8 -175.5(4) . . . . ?
Fe1 C6 C7 C8 59.0(3) . . . . ?
C10 C6 C7 Fe1 -58.7(3) . . . . ?
P1 C6 C7 Fe1 125.5(4) . . . . ?
C6 C10 C9 C8 0.9(5) . . . . ?
C11 C10 C9 C8 178.6(4) . . . . ?
Fe1 C10 C9 C8 -58.7(4) . . . . ?
C6 C10 C9 Fe1 59.6(3) . . . . ?
C11 C10 C9 Fe1 -122.7(4) . . . . ?
C10 C9 C8 C7 -0.6(6) . . . . ?
Fe1 C9 C8 C7 -59.3(4) . . . . ?
C10 C9 C8 Fe1 58.7(3) . . . . ?
C6 C7 C8 C9 0.1(6) . . . . ?
Fe1 C7 C8 C9 59.4(4) . . . . ?
C6 C7 C8 Fe1 -59.3(3) . . . . ?
C1 C2 C3 C4 -0.1(8) . . . . ?
Fe1 C2 C3 C4 -59.2(5) . . . . ?
C1 C2 C3 Fe1 59.0(5) . . . . ?
C5 C4 C3 C2 -1.0(8) . . . . ?
Fe1 C4 C3 C2 60.2(5) . . . . ?
C5 C4 C3 Fe1 -61.2(4) . . . . ?
C3 C4 C5 C1 1.8(7) . . . . ?
Fe1 C4 C5 C1 -59.9(5) . . . . ?
C3 C4 C5 Fe1 61.7(4) . . . . ?
C4 C5 C1 C2 -1.9(8) . . . . ?
Fe1 C5 C1 C2 -61.3(5) . . . . ?
C4 C5 C1 Fe1 59.4(4) . . . . ?
C3 C2 C1 C5 1.3(8) . . . . ?
Fe1 C2 C1 C5 60.5(5) . . . . ?
C3 C2 C1 Fe1 -59.2(5) . . . . ?

_refine_diff_density_max         0.745
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.091

####################################################################### 
# 
# 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_i4mmm_a
_database_code_depnum_ccdc_archive 'CCDC 2021806'
loop_
_audit_author_name
_audit_author_address
'Volodymyr Bon'
;Technische Universitaet Dresden
Germany
;
_audit_update_record             
;
2020-08-06 deposited with the CCDC.	2020-12-08 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT043_i4mmm_a             
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..      86.92 Check 
RESPONSE: Not all atoms of the framework structure could be located from
the difference Fourier map because of disorder
;
_vrf_PLAT051_i4mmm_a             
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      46.95 %     
RESPONSE: Difference in the calculated and reported coefficients is 
explained by the missing disordered atoms
;
_vrf_PLAT307_i4mmm_a             
;
PROBLEM: Isolated Metal Atom found in Structure (Unusual)        Fe1 Check 
RESPONSE: The disordered atoms of the ferrocene moeity could not be located
because of the low occupancy of the corresponding parts. 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        Ni2(bpy)2L2
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H54 Fe2 N6 Ni O4 P2'
_chemical_formula_weight         1011.32

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'
P P 0.1023 0.0942 '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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           139
_space_group_name_H-M_alt        'I 4/m m m'
_space_group_name_Hall           '-I 4 2'

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

_cell_length_a                   11.3027(7)
_cell_length_b                   11.3027(7)
_cell_length_c                   17.8993(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2286.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    385
_cell_measurement_theta_min      8.5
_cell_measurement_theta_max      23.2

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_F_000             1052
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.155
_shelx_estimated_absorpt_T_min   0.785
_shelx_estimated_absorpt_T_max   0.864
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'long-focus X-ray tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            28780
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.131
_diffrn_reflns_theta_max         26.400
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             711
_reflns_number_gt                655
_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    '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)+(0.1999P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         711
_refine_ls_number_parameters     44
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1235
_refine_ls_R_factor_gt           0.1200
_refine_ls_wR_factor_ref         0.3158
_refine_ls_wR_factor_gt          0.3040
_refine_ls_goodness_of_fit_ref   1.537
_refine_ls_restrained_S_all      1.536
_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
Ni1 Ni 0.500000 0.500000 0.500000 0.0591(9) Uani 1 16 d S T P A .
O1 O 0.500000 0.500000 0.3854(4) 0.0692(18) Uani 1 8 d DS T P . .
N1 N 0.500000 0.6870(5) 0.500000 0.0644(15) Uani 1 4 d S T P . .
C1 C 0.4435(12) 0.7484(9) 0.5510(6) 0.101(4) Uani 0.5 1 d . . P A -1
H1 H 0.402157 0.707348 0.587658 0.121 Uiso 0.5 1 calc R U P A -1
C2 C 0.4421(13) 0.8701(9) 0.5533(6) 0.101(3) Uani 0.5 1 d . . P A -1
H2 H 0.401544 0.908665 0.591364 0.121 Uiso 0.5 1 calc R U P A -1
C3 C 0.500000 0.9346(7) 0.500000 0.0684(18) Uani 1 4 d S T P . .
P1 P 0.4587(8) 0.4587(8) 0.3126(4) 0.097(4) Uani 0.15 2 d DS T P . .
Fe1 Fe 0.3638(14) 0.500000 0.1683(6) 0.518(15) Uani 0.5 2 d S T P . .


_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
Ni1 O1 2.052(8) . ?
Ni1 O1 2.052(8) 17_666 ?
Ni1 N1 2.114(6) . ?
Ni1 N1 2.114(6) 19_566 ?
Ni1 N1 2.114(6) 17_666 ?
Ni1 N1 2.114(6) 3_655 ?
O1 P1 1.460(10) 4_565 ?
O1 P1 1.460(10) 3_655 ?
O1 P1 1.460(10) 2_665 ?
O1 P1 1.460(10) . ?
N1 C1 1.312(9) . ?
C1 C2 1.376(13) . ?
C1 H1 0.9300 . ?
C2 C3 1.368(10) . ?
C2 H2 0.9300 . ?
C3 C3 1.478(15) 17_676 ?
P1 P1 0.933(18) 4_565 ?
P1 P1 0.933(18) 3_655 ?
P1 P1 1.32(3) 2_665 ?
P1 Fe1 2.836(13) . ?
P1 Fe1 2.836(13) 3_655 ?
Fe1 Fe1 2.18(2) 4_565 ?
Fe1 Fe1 2.18(2) 3_655 ?

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 Ni1 O1 180.0 . 17_666 ?
O1 Ni1 N1 90.000(1) . . ?
O1 Ni1 N1 90.000(1) 17_666 . ?
O1 Ni1 N1 90.000(1) . 19_566 ?
O1 Ni1 N1 90.000(1) 17_666 19_566 ?
N1 Ni1 N1 90.000(2) . 19_566 ?
O1 Ni1 N1 90.000(1) . 17_666 ?
O1 Ni1 N1 90.000(1) 17_666 17_666 ?
N1 Ni1 N1 180.0 . 17_666 ?
N1 Ni1 N1 90.000(1) 19_566 17_666 ?
O1 Ni1 N1 90.000(1) . 3_655 ?
O1 Ni1 N1 90.000(1) 17_666 3_655 ?
N1 Ni1 N1 90.000(1) . 3_655 ?
N1 Ni1 N1 180.0 19_566 3_655 ?
N1 Ni1 N1 90.000(2) 17_666 3_655 ?
P1 O1 P1 53.7(11) 4_565 3_655 ?
P1 O1 P1 37.3(7) 4_565 2_665 ?
P1 O1 P1 37.3(7) 3_655 2_665 ?
P1 O1 P1 37.3(7) 4_565 . ?
P1 O1 P1 37.3(7) 3_655 . ?
P1 O1 P1 53.7(11) 2_665 . ?
P1 O1 Ni1 153.1(5) 4_565 . ?
P1 O1 Ni1 153.1(5) 3_655 . ?
P1 O1 Ni1 153.1(5) 2_665 . ?
P1 O1 Ni1 153.1(5) . . ?
C1 N1 Ni1 121.9(5) . . ?
N1 C1 C2 123.7(8) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C3 C2 C1 120.4(8) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C3 122.2(5) . 17_676 ?
P1 P1 P1 90.000(5) 4_565 3_655 ?
P1 P1 P1 45.000(1) 4_565 2_665 ?
P1 P1 P1 45.0 3_655 2_665 ?
P1 P1 O1 71.4(4) 4_565 . ?
P1 P1 O1 71.4(4) 3_655 . ?
P1 P1 O1 63.1(5) 2_665 . ?
P1 P1 Fe1 80.53(19) 4_565 . ?
P1 P1 Fe1 112.2(4) 3_655 . ?
P1 P1 Fe1 98.7(4) 2_665 . ?
O1 P1 Fe1 151.8(5) . . ?
P1 P1 Fe1 112.2(4) 4_565 3_655 ?
P1 P1 Fe1 80.53(18) 3_655 3_655 ?
P1 P1 Fe1 98.7(4) 2_665 3_655 ?
O1 P1 Fe1 151.8(5) . 3_655 ?
Fe1 P1 Fe1 45.1(5) . 3_655 ?
Fe1 Fe1 Fe1 90.001(2) 4_565 3_655 ?
Fe1 Fe1 P1 81.3(4) 4_565 . ?
Fe1 Fe1 P1 67.4(2) 3_655 . ?
Fe1 Fe1 P1 67.4(2) 4_565 4_565 ?
Fe1 Fe1 P1 81.3(4) 3_655 4_565 ?
P1 Fe1 P1 18.9(4) . 4_565 ?

_refine_diff_density_max         1.060
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.191

