# 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_mil15
_database_code_depnum_ccdc_archive 'CCDC 1946867'
loop_
_audit_author_name
_audit_author_address
'Zilya Yamaleeva'
;Arbuzov Institute of Organic and Physical Chemistry,  FRC Kazan Scientific Center of RAS
Russia
;
_audit_update_record             
;
2019-08-13 deposited with the CCDC.	2019-10-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H14 Co Fe O6 P2, 2(H2 O)'
_chemical_formula_sum            'C10 H18 Co Fe O8 P2'
_chemical_formula_weight         442.96

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'
Co Co 0.3494 0.9721 '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'
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                   10.0734(6)
_cell_length_b                   5.3953(3)
_cell_length_c                   13.2485(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.316(3)
_cell_angle_gamma                90
_cell_volume                     710.55(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3657
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      32.69

_exptl_crystal_description       prizm
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.070
_exptl_crystal_F_000             450
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.153
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.087
_exptl_absorpt_coefficient_mu    2.451
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6694
_exptl_absorpt_correction_T_max  0.7468
_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10412
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.049
_diffrn_reflns_theta_max         27.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1718
_reflns_number_gt                1416
_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       'APEX3 v2018.1-0'
_computing_data_reduction        'SAINT NT v6.0 (Bruker AXS, 2003)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Mercury CSD 4.1.0'
_computing_publication_material  'enCIFer Version 1.7.1'
_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)+(0.0318P)²+0.6887P] 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         1718
_refine_ls_number_parameters     123
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0761
_refine_ls_wR_factor_gt          0.0718
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.095
_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
Co1 Co 0.500000 0.000000 0.500000 0.01157(12) Uani 1 2 d S . P . .
Fe1 Fe 0.000000 0.500000 0.500000 0.01155(12) Uani 1 2 d S . P . .
P1 P 0.33498(6) 0.48538(10) 0.54169(4) 0.01192(14) Uani 1 1 d . . . . .
O1 O 0.43638(15) 0.6883(3) 0.57484(12) 0.0151(3) Uani 1 1 d . . . . .
O2 O 0.37817(16) 0.2237(3) 0.57264(12) 0.0155(3) Uani 1 1 d . . . . .
O3 O 0.34222(18) -0.0430(3) 0.36576(14) 0.0208(4) Uani 1 1 d D . . . .
H3A H 0.347(3) -0.151(4) 0.3300(18) 0.045(11) Uiso 1 1 d D . . . .
H3B H 0.339(3) 0.065(3) 0.3288(17) 0.030(9) Uiso 1 1 d D . . . .
O1W O 0.6397(2) 0.5243(4) 0.73045(17) 0.0326(5) Uani 1 1 d . . . . .
H1WA H 0.578(4) 0.561(7) 0.698(3) 0.044(12) Uiso 1 1 d . . . . .
H1WB H 0.628(4) 0.554(7) 0.786(3) 0.058(13) Uiso 1 1 d . . . . .
C5 C 0.1833(2) 0.5522(4) 0.58902(16) 0.0132(4) Uani 1 1 d . . . . .
C4 C 0.1121(2) 0.7815(4) 0.57319(17) 0.0160(4) Uani 1 1 d . . . . .
H4 H 0.140930 0.922310 0.542503 0.019 Uiso 1 1 calc R U . . .
C1 C 0.1032(2) 0.3881(4) 0.63917(17) 0.0143(4) Uani 1 1 d . . . . .
H1A H 0.125317 0.226036 0.659122 0.017 Uiso 1 1 calc R U . . .
C2 C -0.0155(2) 0.5150(4) 0.65314(17) 0.0175(5) Uani 1 1 d . . . . .
H2 H -0.084826 0.450645 0.683752 0.021 Uiso 1 1 calc R U . . .
C3 C -0.0104(2) 0.7575(5) 0.61237(17) 0.0184(5) Uani 1 1 d . . . . .
H3 H -0.075826 0.879322 0.611484 0.022 Uiso 1 1 calc R U . . .
H1 H 0.306(3) 0.496(4) 0.438(2) 0.014(7) 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
Co1 O2 2.0666(15) 3_656 ?
Co1 O2 2.0666(15) . ?
Co1 O1 2.1041(15) 3_666 ?
Co1 O1 2.1041(15) 1_545 ?
Co1 O3 2.1972(18) . ?
Co1 O3 2.1972(18) 3_656 ?
Fe1 C4 2.041(2) . ?
Fe1 C4 2.041(2) 3_566 ?
Fe1 C5 2.043(2) 3_566 ?
Fe1 C5 2.043(2) . ?
Fe1 C3 2.051(2) . ?
Fe1 C3 2.051(2) 3_566 ?
Fe1 C1 2.055(2) . ?
Fe1 C1 2.055(2) 3_566 ?
Fe1 C2 2.061(2) 3_566 ?
Fe1 C2 2.061(2) . ?
P1 O1 1.5132(16) . ?
P1 O2 1.5144(16) . ?
P1 C5 1.780(2) . ?
P1 H1 1.36(3) . ?
O3 H3A 0.7599(10) . ?
O3 H3B 0.7599(10) . ?
O1W H1WA 0.72(4) . ?
O1W H1WB 0.78(4) . ?
C5 C4 1.429(3) . ?
C5 C1 1.432(3) . ?
C4 C3 1.419(3) . ?
C4 H4 0.9300 . ?
C1 C2 1.416(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.419(3) . ?
C2 H2 0.9300 . ?
C3 H3 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
O2 Co1 O2 180.00(9) 3_656 . ?
O2 Co1 O1 89.89(6) 3_656 3_666 ?
O2 Co1 O1 90.11(6) . 3_666 ?
O2 Co1 O1 90.11(6) 3_656 1_545 ?
O2 Co1 O1 89.89(6) . 1_545 ?
O1 Co1 O1 180.0 3_666 1_545 ?
O2 Co1 O3 88.15(7) 3_656 . ?
O2 Co1 O3 91.85(7) . . ?
O1 Co1 O3 86.48(6) 3_666 . ?
O1 Co1 O3 93.52(6) 1_545 . ?
O2 Co1 O3 91.85(7) 3_656 3_656 ?
O2 Co1 O3 88.15(7) . 3_656 ?
O1 Co1 O3 93.53(6) 3_666 3_656 ?
O1 Co1 O3 86.47(6) 1_545 3_656 ?
O3 Co1 O3 180.0 . 3_656 ?
C4 Fe1 C4 180.0 . 3_566 ?
C4 Fe1 C5 139.05(9) . 3_566 ?
C4 Fe1 C5 40.95(9) 3_566 3_566 ?
C4 Fe1 C5 40.95(9) . . ?
C4 Fe1 C5 139.05(9) 3_566 . ?
C5 Fe1 C5 180.0 3_566 . ?
C4 Fe1 C3 40.58(9) . . ?
C4 Fe1 C3 139.42(9) 3_566 . ?
C5 Fe1 C3 111.40(9) 3_566 . ?
C5 Fe1 C3 68.60(9) . . ?
C4 Fe1 C3 139.42(9) . 3_566 ?
C4 Fe1 C3 40.58(9) 3_566 3_566 ?
C5 Fe1 C3 68.60(9) 3_566 3_566 ?
C5 Fe1 C3 111.40(9) . 3_566 ?
C3 Fe1 C3 180.0 . 3_566 ?
C4 Fe1 C1 68.41(9) . . ?
C4 Fe1 C1 111.59(9) 3_566 . ?
C5 Fe1 C1 139.11(9) 3_566 . ?
C5 Fe1 C1 40.89(9) . . ?
C3 Fe1 C1 68.01(9) . . ?
C3 Fe1 C1 111.99(9) 3_566 . ?
C4 Fe1 C1 111.59(9) . 3_566 ?
C4 Fe1 C1 68.41(9) 3_566 3_566 ?
C5 Fe1 C1 40.89(9) 3_566 3_566 ?
C5 Fe1 C1 139.11(9) . 3_566 ?
C3 Fe1 C1 111.99(9) . 3_566 ?
C3 Fe1 C1 68.01(9) 3_566 3_566 ?
C1 Fe1 C1 180.0 . 3_566 ?
C4 Fe1 C2 111.88(9) . 3_566 ?
C4 Fe1 C2 68.12(9) 3_566 3_566 ?
C5 Fe1 C2 68.39(9) 3_566 3_566 ?
C5 Fe1 C2 111.61(9) . 3_566 ?
C3 Fe1 C2 139.62(9) . 3_566 ?
C3 Fe1 C2 40.38(9) 3_566 3_566 ?
C1 Fe1 C2 139.78(9) . 3_566 ?
C1 Fe1 C2 40.23(9) 3_566 3_566 ?
C4 Fe1 C2 68.12(9) . . ?
C4 Fe1 C2 111.88(9) 3_566 . ?
C5 Fe1 C2 111.61(9) 3_566 . ?
C5 Fe1 C2 68.39(9) . . ?
C3 Fe1 C2 40.38(9) . . ?
C3 Fe1 C2 139.62(9) 3_566 . ?
C1 Fe1 C2 40.23(9) . . ?
C1 Fe1 C2 139.77(9) 3_566 . ?
C2 Fe1 C2 180.00(12) 3_566 . ?
O1 P1 O2 116.44(9) . . ?
O1 P1 C5 109.19(10) . . ?
O2 P1 C5 108.59(10) . . ?
O1 P1 H1 106.9(10) . . ?
O2 P1 H1 108.6(9) . . ?
C5 P1 H1 106.8(11) . . ?
P1 O1 Co1 133.18(10) . 1_565 ?
P1 O2 Co1 125.77(9) . . ?
Co1 O3 H3A 118(3) . . ?
Co1 O3 H3B 113(2) . . ?
H3A O3 H3B 101(3) . . ?
H1WA O1W H1WB 105(4) . . ?
C4 C5 C1 107.23(19) . . ?
C4 C5 P1 124.27(17) . . ?
C1 C5 P1 128.22(17) . . ?
C4 C5 Fe1 69.45(12) . . ?
C1 C5 Fe1 70.00(12) . . ?
P1 C5 Fe1 121.05(11) . . ?
C3 C4 C5 108.2(2) . . ?
C3 C4 Fe1 70.07(13) . . ?
C5 C4 Fe1 69.60(13) . . ?
C3 C4 H4 125.9 . . ?
C5 C4 H4 125.9 . . ?
Fe1 C4 H4 126.0 . . ?
C2 C1 C5 108.2(2) . . ?
C2 C1 Fe1 70.12(13) . . ?
C5 C1 Fe1 69.11(12) . . ?
C2 C1 H1A 125.9 . . ?
C5 C1 H1A 125.9 . . ?
Fe1 C1 H1A 126.5 . . ?
C1 C2 C3 108.2(2) . . ?
C1 C2 Fe1 69.65(13) . . ?
C3 C2 Fe1 69.42(13) . . ?
C1 C2 H2 125.9 . . ?
C3 C2 H2 125.9 . . ?
Fe1 C2 H2 126.6 . . ?
C2 C3 C4 108.1(2) . . ?
C2 C3 Fe1 70.20(13) . . ?
C4 C3 Fe1 69.34(13) . . ?
C2 C3 H3 125.9 . . ?
C4 C3 H3 125.9 . . ?
Fe1 C3 H3 126.1 . . ?

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
O2 P1 O1 Co1 136.29(12) . . . 1_565 ?
C5 P1 O1 Co1 -100.34(14) . . . 1_565 ?
O1 P1 O2 Co1 -79.98(13) . . . . ?
C5 P1 O2 Co1 156.33(11) . . . . ?
O1 P1 C5 C4 53.0(2) . . . . ?
O2 P1 C5 C4 -179.09(18) . . . . ?
O1 P1 C5 C1 -133.8(2) . . . . ?
O2 P1 C5 C1 -5.9(2) . . . . ?
O1 P1 C5 Fe1 138.09(12) . . . . ?
O2 P1 C5 Fe1 -93.99(14) . . . . ?
C1 C5 C4 C3 -0.4(2) . . . . ?
P1 C5 C4 C3 173.94(16) . . . . ?
Fe1 C5 C4 C3 59.65(15) . . . . ?
C1 C5 C4 Fe1 -60.09(15) . . . . ?
P1 C5 C4 Fe1 114.28(17) . . . . ?
C4 C5 C1 C2 0.3(2) . . . . ?
P1 C5 C1 C2 -173.74(17) . . . . ?
Fe1 C5 C1 C2 -59.41(15) . . . . ?
C4 C5 C1 Fe1 59.74(15) . . . . ?
P1 C5 C1 Fe1 -114.34(18) . . . . ?
C5 C1 C2 C3 -0.1(3) . . . . ?
Fe1 C1 C2 C3 -58.89(15) . . . . ?
C5 C1 C2 Fe1 58.77(15) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
Fe1 C2 C3 C4 -59.19(15) . . . . ?
C1 C2 C3 Fe1 59.03(15) . . . . ?
C5 C4 C3 C2 0.4(3) . . . . ?
Fe1 C4 C3 C2 59.73(16) . . . . ?
C5 C4 C3 Fe1 -59.36(15) . . . . ?

_refine_diff_density_max         0.485
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.087

