# 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 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1812311'
_audit_update_record             
;
2018-11-22 deposited with the CCDC.
2018-11-27 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         'H12 Ni O6, 2(C9 H15 F N Ni O8 P2), 4(H2 O)'
_chemical_formula_sum            'C18 H50 F2 N2 Ni3 O26 P4'
_chemical_formula_weight         1048.61

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'
F F 0.0171 0.0103 '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'
Ni Ni 0.3393 1.1124 '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                   19.126(2)
_cell_length_b                   6.2821(6)
_cell_length_c                   15.7341(18)
_cell_angle_alpha                90
_cell_angle_beta                 106.417(4)
_cell_angle_gamma                90
_cell_volume                     1813.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1960
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      25.13

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.920
_exptl_crystal_F_000             1084
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.828
_shelx_estimated_absorpt_T_min   0.679
_shelx_estimated_absorpt_T_max   0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6716
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10322
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.971
_diffrn_reflns_theta_max         25.329
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3312
_reflns_number_gt                2126
_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       'SMART (Bruker AXS, 2000)'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    water
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEPII(Johnson,1976)andPLUTON(Spek,1990)
_computing_publication_material  'SHELXL97(Sheldrick, 1997)'
_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)+(0.0344P)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         3312
_refine_ls_number_parameters     295
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.0929
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.035
_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
C1 C 0.4271(3) 0.5933(11) 0.8125(4) 0.0384(17) Uani 1 1 d . . . . .
C2 C 0.4509(3) 0.7534(10) 0.8724(4) 0.0370(16) Uani 1 1 d . . . . .
H2 H 0.4215 0.8704 0.8740 0.044 Uiso 1 1 calc R U . . .
C3 C 0.5198(3) 0.7361(8) 0.9305(4) 0.0272(14) Uani 1 1 d . . . . .
H3 H 0.5366 0.8441 0.9716 0.033 Uiso 1 1 calc R U . . .
C4 C 0.5647(3) 0.5644(8) 0.9298(3) 0.0162(12) Uani 1 1 d . . . . .
C5 C 0.5368(3) 0.4026(8) 0.8682(4) 0.0259(13) Uani 1 1 d . . . . .
H5 H 0.5652 0.2832 0.8667 0.031 Uiso 1 1 calc R U . . .
C6 C 0.4680(3) 0.4176(10) 0.8099(4) 0.0389(16) Uani 1 1 d . . . . .
H6 H 0.4498 0.3093 0.7693 0.047 Uiso 1 1 calc R U . . .
C7 C 0.6402(2) 0.5418(7) 0.9932(3) 0.0136(11) Uani 1 1 d . . . . .
H7A H 0.6410 0.6156 1.0477 0.016 Uiso 1 1 calc R U . . .
H7B H 0.6488 0.3921 1.0076 0.016 Uiso 1 1 calc R U . . .
C8 C 0.7018(3) 0.8624(6) 0.9555(3) 0.0110(11) Uani 1 1 d . . . . .
H8A H 0.6527 0.9145 0.9481 0.013 Uiso 1 1 calc R U . . .
H8B H 0.7166 0.9052 0.9039 0.013 Uiso 1 1 calc R U . . .
C9 C 0.7021(2) 0.5301(7) 0.8740(3) 0.0105(10) Uani 1 1 d . . . . .
H9A H 0.6645 0.5981 0.8273 0.013 Uiso 1 1 calc R U . . .
H9B H 0.6905 0.3798 0.8739 0.013 Uiso 1 1 calc R U . . .
F1 F 0.35933(18) 0.6075(7) 0.7543(2) 0.0628(12) Uani 1 1 d . . . . .
H1A H 0.741(3) 1.014(10) 1.172(2) 0.075 Uiso 1 1 d D U . . .
H10A H 0.993(3) 0.661(8) 0.643(4) 0.075 Uiso 1 1 d D U . . .
H11A H 0.879(4) 0.303(6) 0.438(5) 0.075 Uiso 1 1 d D U . . .
H12A H 0.8892(19) 0.321(11) 0.778(5) 0.075 Uiso 1 1 d D U . . .
H13A H 0.958(3) 0.842(10) 0.804(3) 0.075 Uiso 1 1 d D U . . .
H10B H 0.9262(15) 0.595(11) 0.606(5) 0.075 Uiso 1 1 d D U . . .
H11B H 0.862(3) 0.495(9) 0.406(4) 0.075 Uiso 1 1 d D U . . .
H12B H 0.940(4) 0.458(4) 0.776(5) 0.075 Uiso 1 1 d D U . . .
H13B H 0.888(2) 0.791(11) 0.779(4) 0.075 Uiso 1 1 d D U . . .
H7C H 0.772(4) 0.583(8) 1.201(3) 0.075 Uiso 1 1 d D U . . .
H8C H 0.919(4) 0.538(7) 1.164(3) 0.075 Uiso 1 1 d D U . . .
H9C H 1.058(3) 0.125(10) 0.542(5) 0.075 Uiso 1 1 d D U . . .
H7D H 0.766(4) 0.383(6) 1.190(4) 0.075 Uiso 1 1 d D U . . .
H8D H 0.914(4) 0.326(6) 1.153(4) 0.075 Uiso 1 1 d D U . . .
H9D H 0.997(3) 0.111(9) 0.558(5) 0.075 Uiso 1 1 d D U . . .
N1 N 0.7019(2) 0.6242(5) 0.9610(2) 0.0085(9) Uani 1 1 d . . . . .
Ni1 Ni 0.80495(3) 0.51295(9) 1.05102(4) 0.01181(17) Uani 1 1 d . . . . .
Ni2 Ni 1.0000 0.5000 0.5000 0.0114(2) Uani 1 2 d S . P . .
O1 O 0.71748(19) 0.9810(6) 1.1219(2) 0.0214(8) Uani 1 1 d D . . . .
O2 O 0.82710(17) 0.8311(4) 1.0801(2) 0.0136(8) Uani 1 1 d . . . . .
O3 O 0.77942(19) 1.2016(5) 1.0301(2) 0.0189(8) Uani 1 1 d . . . . .
O4 O 0.84509(17) 0.5048(5) 0.93984(18) 0.0131(7) Uani 1 1 d . . . . .
O5 O 0.80062(18) 0.7871(5) 0.8227(2) 0.0158(8) Uani 1 1 d . . . . .
O6 O 0.78838(18) 0.4016(5) 0.7778(2) 0.0153(8) Uani 1 1 d . . . . .
O7 O 0.7665(2) 0.4934(5) 1.1634(2) 0.0204(8) Uani 1 1 d D . . . .
O8 O 0.9108(2) 0.4408(5) 1.1271(2) 0.0175(8) Uani 1 1 d D . . . .
O9 O 1.0231(2) 0.1964(5) 0.5438(3) 0.0232(9) Uani 1 1 d D . . . .
O10 O 0.96925(19) 0.5654(5) 0.6121(2) 0.0166(8) Uani 1 1 d D . . . .
O11 O 0.8955(2) 0.4191(5) 0.4312(2) 0.0198(8) Uani 1 1 d D . . . .
O12 O 0.9299(2) 0.3334(6) 0.7702(3) 0.0251(9) Uani 1 1 d D . . . .
O13 O 0.9271(2) 0.7863(6) 0.7634(3) 0.0238(9) Uani 1 1 d D . . . .
P1 P 0.76232(6) 0.98074(18) 1.05313(8) 0.0105(3) Uani 1 1 d . . . . .
P2 P 0.78950(7) 0.56178(18) 0.85120(8) 0.0113(3) Uani 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
C1 C6 1.360(9) . ?
C1 F1 1.363(6) . ?
C1 C2 1.364(8) . ?
C2 C3 1.380(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.401(7) . ?
C4 C7 1.511(6) . ?
C5 C6 1.379(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.503(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.498(5) . ?
C8 P1 1.802(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.492(5) . ?
C9 P2 1.817(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
N1 Ni1 2.190(4) . ?
Ni1 O3 2.020(3) 1_545 ?
Ni1 O2 2.067(3) . ?
Ni1 O8 2.090(4) . ?
Ni1 O4 2.100(3) . ?
Ni1 O7 2.101(3) . ?
Ni2 O9 2.034(3) 3_766 ?
Ni2 O9 2.034(3) . ?
Ni2 O11 2.050(4) 3_766 ?
Ni2 O11 2.050(4) . ?
Ni2 O10 2.052(4) 3_766 ?
Ni2 O10 2.052(4) . ?
O1 P1 1.559(4) . ?
O1 H1A 0.81(2) . ?
O2 P1 1.517(3) . ?
O3 P1 1.493(3) . ?
O3 Ni1 2.020(3) 1_565 ?
O4 P2 1.538(3) . ?
O5 P2 1.518(3) . ?
O6 P2 1.527(3) . ?
O7 H7C 0.81(2) . ?
O7 H7D 0.81(2) . ?
O8 H8C 0.82(2) . ?
O8 H8D 0.82(2) . ?
O9 H9C 0.82(2) . ?
O9 H9D 0.81(2) . ?
O10 H10A 0.82(2) . ?
O10 H10B 0.82(2) . ?
O11 H11A 0.81(2) . ?
O11 H11B 0.80(2) . ?
O12 H12A 0.82(2) . ?
O12 H12B 0.81(2) . ?
O13 H13A 0.82(2) . ?
O13 H13B 0.84(2) . ?

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
C6 C1 F1 118.5(6) . . ?
C6 C1 C2 122.5(6) . . ?
F1 C1 C2 118.9(6) . . ?
C1 C2 C3 117.9(6) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C2 C3 C4 122.4(5) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C5 117.1(5) . . ?
C3 C4 C7 123.2(5) . . ?
C5 C4 C7 119.6(4) . . ?
C6 C5 C4 121.1(5) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C1 C6 C5 118.9(6) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
N1 C7 C4 116.1(4) . . ?
N1 C7 H7A 108.3 . . ?
C4 C7 H7A 108.3 . . ?
N1 C7 H7B 108.3 . . ?
C4 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
N1 C8 P1 111.9(3) . . ?
N1 C8 H8A 109.2 . . ?
P1 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
P1 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N1 C9 P2 112.2(3) . . ?
N1 C9 H9A 109.2 . . ?
P2 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
P2 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C9 N1 C8 110.0(3) . . ?
C9 N1 C7 112.2(3) . . ?
C8 N1 C7 112.0(3) . . ?
C9 N1 Ni1 103.4(3) . . ?
C8 N1 Ni1 110.0(3) . . ?
C7 N1 Ni1 108.7(3) . . ?
O3 Ni1 O2 175.59(14) 1_545 . ?
O3 Ni1 O8 91.93(13) 1_545 . ?
O2 Ni1 O8 88.75(12) . . ?
O3 Ni1 O4 88.22(13) 1_545 . ?
O2 Ni1 O4 96.16(12) . . ?
O8 Ni1 O4 87.05(13) . . ?
O3 Ni1 O7 87.41(14) 1_545 . ?
O2 Ni1 O7 88.22(13) . . ?
O8 Ni1 O7 91.03(14) . . ?
O4 Ni1 O7 175.17(13) . . ?
O3 Ni1 N1 94.12(13) 1_545 . ?
O2 Ni1 N1 85.70(12) . . ?
O8 Ni1 N1 171.18(14) . . ?
O4 Ni1 N1 86.74(13) . . ?
O7 Ni1 N1 95.64(14) . . ?
O9 Ni2 O9 180.00(6) 3_766 . ?
O9 Ni2 O11 91.89(15) 3_766 3_766 ?
O9 Ni2 O11 88.11(15) . 3_766 ?
O9 Ni2 O11 88.11(15) 3_766 . ?
O9 Ni2 O11 91.89(15) . . ?
O11 Ni2 O11 180.0 3_766 . ?
O9 Ni2 O10 89.09(15) 3_766 3_766 ?
O9 Ni2 O10 90.91(15) . 3_766 ?
O11 Ni2 O10 91.74(15) 3_766 3_766 ?
O11 Ni2 O10 88.26(15) . 3_766 ?
O9 Ni2 O10 90.91(15) 3_766 . ?
O9 Ni2 O10 89.09(15) . . ?
O11 Ni2 O10 88.26(15) 3_766 . ?
O11 Ni2 O10 91.73(15) . . ?
O10 Ni2 O10 180.0 3_766 . ?
P1 O1 H1A 114(5) . . ?
P1 O2 Ni1 115.92(17) . . ?
P1 O3 Ni1 156.8(2) . 1_565 ?
P2 O4 Ni1 115.33(18) . . ?
Ni1 O7 H7C 126(5) . . ?
Ni1 O7 H7D 122(5) . . ?
H7C O7 H7D 104(7) . . ?
Ni1 O8 H8C 101(5) . . ?
Ni1 O8 H8D 114(5) . . ?
H8C O8 H8D 109(6) . . ?
Ni2 O9 H9C 127(5) . . ?
Ni2 O9 H9D 128(5) . . ?
H9C O9 H9D 104(7) . . ?
Ni2 O10 H10A 114(5) . . ?
Ni2 O10 H10B 117(5) . . ?
H10A O10 H10B 106(6) . . ?
Ni2 O11 H11A 120(5) . . ?
Ni2 O11 H11B 129(5) . . ?
H11A O11 H11B 109(7) . . ?
H12A O12 H12B 106(7) . . ?
H13A O13 H13B 105(7) . . ?
O3 P1 O2 115.20(19) . . ?
O3 P1 O1 111.6(2) . . ?
O2 P1 O1 111.9(2) . . ?
O3 P1 C8 107.96(19) . . ?
O2 P1 C8 105.04(19) . . ?
O1 P1 C8 104.2(2) . . ?
O5 P2 O6 111.39(19) . . ?
O5 P2 O4 111.47(18) . . ?
O6 P2 O4 112.99(18) . . ?
O5 P2 C9 111.9(2) . . ?
O6 P2 C9 105.08(19) . . ?
O4 P2 C9 103.55(19) . . ?

_refine_diff_density_max         0.467
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.114



