# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_I
_database_code_depnum_ccdc_archive 'CCDC 1575157'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2018-01-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H40 Ni O2 P2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         489.25

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3584(7)
_cell_length_b                   11.8024(9)
_cell_length_c                   13.3916(11)
_cell_angle_alpha                99.952(2)
_cell_angle_beta                 95.864(2)
_cell_angle_gamma                104.444(2)
_cell_volume                     1245.36(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4941
_cell_measurement_theta_min      2.5460
_cell_measurement_theta_max      30.4451
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.160
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524

_exptl_absorpt_coefficient_mu    1.006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.86

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            47749
_diffrn_reflns_av_R_equivalents  0.1067
_diffrn_reflns_av_unetI/netI     0.0875
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         33.90
_diffrn_reflns_theta_full        33.90
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
;

_reflns_number_total             10021
_reflns_number_gt                7449
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1153
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.026
_refine_ls_number_reflns         10021
_refine_ls_number_parameters     327
_refine_ls_number_restraints     106
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²+0.2520P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.561
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
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'
S S 0.1246 0.1234 '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'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni1 0.52852(3) 0.22632(2) 0.26548(2) 0.00962(6) Uani d . . . 1.0 . .
C C1 0.3997(2) 0.23622(15) 0.14344(13) 0.0098(3) Uani d . . . 1.0 . .
C C2 0.2573(2) 0.14638(15) 0.09422(13) 0.0098(3) Uani d . . . 1.0 . .
C C3 0.1611(2) 0.15072(16) 0.00483(13) 0.0124(3) Uani d . . . 1.0 . .
H H3 0.0658 0.0868 -0.0265 0.015 Uiso calc U . R 1.0 . .
C C4 0.2083(2) 0.25146(16) -0.03749(13) 0.0133(3) Uani d . . . 1.0 . .
H H4 0.1432 0.2567 -0.098 0.016 Uiso calc U . R 1.0 . .
C C5 0.3493(2) 0.34468(16) 0.00717(13) 0.0139(3) Uani d . . . 1.0 . .
H H5 0.3817 0.4131 -0.0222 0.017 Uiso calc U . R 1.0 . .
C C6 0.4409(2) 0.33425(15) 0.09604(13) 0.0106(3) Uani d . . . 1.0 . .
C C7 0.8854(2) 0.39479(17) 0.20291(14) 0.0152(3) Uani d . . . 1.0 . .
C C8 0.8590(3) 0.26502(19) 0.14570(17) 0.0259(5) Uani d . . . 1.0 . .
H H8A 0.7648 0.244 0.0898 0.039 Uiso calc U . R 1.0 . .
H H8B 0.8351 0.211 0.1935 0.039 Uiso calc U . R 1.0 . .
H H8C 0.9604 0.2575 0.1174 0.039 Uiso calc U . R 1.0 . .
C C9 0.9369(3) 0.4785(2) 0.12878(17) 0.0267(5) Uani d . . . 1.0 . .
H H9A 0.953 0.5615 0.1638 0.04 Uiso calc U . R 1.0 . .
H H9B 0.8491 0.4582 0.0692 0.04 Uiso calc U . R 1.0 . .
H H9C 1.0416 0.4693 0.1061 0.04 Uiso calc U . R 1.0 . .
C C10 1.0250(2) 0.4240(2) 0.29476(16) 0.0224(4) Uani d . . . 1.0 . .
H H10A 1.1255 0.4072 0.2711 0.034 Uiso calc U . R 1.0 . .
H H10B 0.9886 0.3747 0.3444 0.034 Uiso calc U . R 1.0 . .
H H10C 1.0501 0.5087 0.3274 0.034 Uiso calc U . R 1.0 . .
C C11 0.6869(2) 0.53547(16) 0.33800(14) 0.0136(3) Uani d . . . 1.0 . .
C C12 0.7756(3) 0.65036(16) 0.30485(16) 0.0200(4) Uani d . . . 1.0 . .
H H12A 0.7591 0.7197 0.3502 0.03 Uiso calc U . R 1.0 . .
H H12B 0.7289 0.6478 0.2341 0.03 Uiso calc U . R 1.0 . .
H H12C 0.8954 0.6568 0.3091 0.03 Uiso calc U . R 1.0 . .
C C13 0.7688(3) 0.53437(18) 0.44548(14) 0.0238(4) Uani d . . . 1.0 . .
H H13A 0.8874 0.5391 0.4449 0.036 Uiso calc U . R 1.0 . .
H H13B 0.7133 0.4602 0.4658 0.036 Uiso calc U . R 1.0 . .
H H13C 0.758 0.603 0.4945 0.036 Uiso calc U . R 1.0 . .
C C14 0.5026(3) 0.53292(19) 0.34168(18) 0.0250(4) Uani d . . . 1.0 . .
H H14A 0.445 0.4599 0.3629 0.038 Uiso calc U . R 1.0 . .
H H14B 0.4489 0.5343 0.2735 0.038 Uiso calc U . R 1.0 . .
H H14C 0.4966 0.6029 0.391 0.038 Uiso calc U . R 1.0 . .
C C15 0.4019(2) -0.08424(16) 0.20648(14) 0.0150(3) Uani d U . D 1.0 . .
C C16 0.4831(9) -0.0645(7) 0.1085(5) 0.0209(11) Uani d U P D 0.65(2) A 1
H H16A 0.5766 0.0082 0.1257 0.031 Uiso calc U P R 0.65(2) A 1
H H16B 0.3995 -0.0561 0.0554 0.031 Uiso calc U P R 0.65(2) A 1
H H16C 0.5242 -0.1332 0.0829 0.031 Uiso calc U P R 0.65(2) A 1
C C17 0.2581(13) -0.1986(10) 0.1749(8) 0.0175(14) Uani d U P D 0.65(2) A 1
H H17A 0.3012 -0.2653 0.1465 0.026 Uiso calc U P R 0.65(2) A 1
H H17B 0.1747 -0.1881 0.1228 0.026 Uiso calc U P R 0.65(2) A 1
H H17C 0.2063 -0.2157 0.235 0.026 Uiso calc U P R 0.65(2) A 1
C C18 0.5330(10) -0.1001(7) 0.2858(6) 0.0248(12) Uani d U P D 0.65(2) A 1
H H18A 0.4837 -0.1151 0.3472 0.037 Uiso calc U P R 0.65(2) A 1
H H18B 0.6264 -0.0273 0.3041 0.037 Uiso calc U P R 0.65(2) A 1
H H18C 0.5738 -0.168 0.2574 0.037 Uiso calc U P R 0.65(2) A 1
C C16A 0.527(2) -0.0595(14) 0.1344(14) 0.030(3) Uani d U P D 0.35(2) A 2
H H16D 0.5412 -0.1352 0.0983 0.046 Uiso calc U P R 0.35(2) A 2
H H16E 0.6346 -0.0098 0.1736 0.046 Uiso calc U P R 0.35(2) A 2
H H16F 0.4871 -0.0172 0.0844 0.046 Uiso calc U P R 0.35(2) A 2
C C17A 0.251(2) -0.1902(17) 0.1583(15) 0.014(2) Uani d U P D 0.35(2) A 2
H H17D 0.1803 -0.1667 0.1069 0.021 Uiso calc U P R 0.35(2) A 2
H H17E 0.186 -0.2144 0.2117 0.021 Uiso calc U P R 0.35(2) A 2
H H17F 0.2893 -0.2572 0.1253 0.021 Uiso calc U P R 0.35(2) A 2
C C18A 0.490(2) -0.1136(13) 0.3049(9) 0.024(2) Uani d U P D 0.35(2) A 2
H H18D 0.5274 -0.1853 0.2853 0.036 Uiso calc U P R 0.35(2) A 2
H H18E 0.41 -0.1275 0.3534 0.036 Uiso calc U P R 0.35(2) A 2
H H18F 0.5859 -0.0461 0.3374 0.036 Uiso calc U P R 0.35(2) A 2
C C19 0.1874(2) 0.04590(16) 0.33786(13) 0.0140(3) Uani d U . D 1.0 . .
C C20 0.0113(6) -0.0349(4) 0.2886(4) 0.0196(8) Uani d U P D 0.700(10) B 1
H H20A -0.065 -0.0341 0.3395 0.029 Uiso calc U P R 0.700(10) B 1
H H20B 0.0174 -0.1168 0.265 0.029 Uiso calc U P R 0.700(10) B 1
H H20C -0.0301 -0.0048 0.2302 0.029 Uiso calc U P R 0.700(10) B 1
C C21 0.2495(5) -0.0057(5) 0.4283(3) 0.0264(10) Uani d U P D 0.700(10) B 1
H H21A 0.3645 0.0402 0.4575 0.04 Uiso calc U P R 0.700(10) B 1
H H21B 0.2461 -0.0895 0.4037 0.04 Uiso calc U P R 0.700(10) B 1
H H21C 0.1771 -0.0005 0.4812 0.04 Uiso calc U P R 0.700(10) B 1
C C22 0.1748(6) 0.1704(3) 0.3741(4) 0.0260(10) Uani d U P D 0.700(10) B 1
H H22A 0.1428 0.2029 0.3149 0.039 Uiso calc U P R 0.700(10) B 1
H H22B 0.2832 0.2209 0.4113 0.039 Uiso calc U P R 0.700(10) B 1
H H22C 0.0901 0.1687 0.4197 0.039 Uiso calc U P R 0.700(10) B 1
C C20A 0.0364(15) -0.0584(9) 0.3106(10) 0.027(2) Uani d U P D 0.300(10) B 2
H H20D 0.0652 -0.1292 0.3274 0.041 Uiso calc U P R 0.300(10) B 2
H H20E -0.0044 -0.0733 0.237 0.041 Uiso calc U P R 0.300(10) B 2
H H20F -0.051 -0.0413 0.3494 0.041 Uiso calc U P R 0.300(10) B 2
C C21A 0.2769(10) 0.0632(11) 0.4490(5) 0.022(2) Uani d U P D 0.300(10) B 2
H H21D 0.1959 0.0651 0.4969 0.033 Uiso calc U P R 0.300(10) B 2
H H21E 0.3656 0.1387 0.4662 0.033 Uiso calc U P R 0.300(10) B 2
H H21F 0.3259 -0.0032 0.4543 0.033 Uiso calc U P R 0.300(10) B 2
C C22A 0.1314(15) 0.1654(8) 0.3373(8) 0.0211(19) Uani d U P D 0.300(10) B 2
H H22D 0.0838 0.1656 0.2674 0.032 Uiso calc U P R 0.300(10) B 2
H H22E 0.2287 0.2348 0.3615 0.032 Uiso calc U P R 0.300(10) B 2
H H22F 0.0472 0.1691 0.3827 0.032 Uiso calc U P R 0.300(10) B 2
O O1 0.58357(16) 0.42531(11) 0.14077(10) 0.0136(2) Uani d . . . 1.0 . .
O O2 0.20959(16) 0.04693(11) 0.13840(9) 0.0124(2) Uani d . . . 1.0 . .
P P1 0.67974(6) 0.39738(4) 0.24442(3) 0.00949(9) Uani d . . . 1.0 . .
P P2 0.33828(6) 0.05581(4) 0.24416(3) 0.00908(9) Uani d . . . 1.0 . .
S S1 0.67720(7) 0.21620(5) 0.40744(4) 0.02669(13) Uani d . . . 1.0 . .
H H1S 0.6124 0.1143 0.4251 0.04 Uiso d U . R 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 C1 . 1.9009(17) ?
Ni1 P1 . 2.1794(5) ?
Ni1 P2 . 2.1845(5) ?
Ni1 S1 . 2.2006(6) ?
C1 C2 . 1.394(2) ?
C1 C6 . 1.400(2) ?
C2 C3 . 1.388(2) ?
C2 O2 . 1.393(2) ?
C3 C4 . 1.391(2) ?
C4 C5 . 1.392(2) ?
C5 C6 . 1.389(2) ?
C6 O1 . 1.389(2) ?
C7 C10 . 1.534(3) ?
C7 C9 . 1.537(3) ?
C7 C8 . 1.540(3) ?
C7 P1 . 1.8659(19) ?
C11 C13 . 1.533(3) ?
C11 C12 . 1.536(3) ?
C11 C14 . 1.539(3) ?
C11 P1 . 1.8603(18) ?
C15 C16A . 1.504(9) ?
C15 C18 . 1.516(6) ?
C15 C17 . 1.528(8) ?
C15 C17A . 1.530(12) ?
C15 C16 . 1.564(5) ?
C15 C18A . 1.575(9) ?
C15 P2 . 1.8639(18) ?
C19 C20A . 1.489(9) ?
C19 C22 . 1.499(4) ?
C19 C21 . 1.547(4) ?
C19 C20 . 1.547(5) ?
C19 C21A . 1.552(6) ?
C19 C22A . 1.594(8) ?
C19 P2 . 1.8652(18) ?
O1 P1 . 1.6564(13) ?
O2 P2 . 1.6599(13) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 Ni1 P1 . . 81.72(5) ?
C1 Ni1 P2 . . 81.83(5) ?
P1 Ni1 P2 . . 163.482(19) ?
C1 Ni1 S1 . . 179.52(5) ?
P1 Ni1 S1 . . 98.07(2) ?
P2 Ni1 S1 . . 98.39(2) ?
C2 C1 C6 . . 114.91(15) ?
C2 C1 Ni1 . . 122.59(12) ?
C6 C1 Ni1 . . 122.50(13) ?
C3 C2 O2 . . 118.62(15) ?
C3 C2 C1 . . 123.95(16) ?
O2 C2 C1 . . 117.43(14) ?
C2 C3 C4 . . 118.04(16) ?
C3 C4 C5 . . 121.29(16) ?
C6 C5 C4 . . 117.77(16) ?
O1 C6 C5 . . 118.66(15) ?
O1 C6 C1 . . 117.30(15) ?
C5 C6 C1 . . 124.03(16) ?
C10 C7 C9 . . 109.58(17) ?
C10 C7 C8 . . 109.08(16) ?
C9 C7 C8 . . 108.47(17) ?
C10 C7 P1 . . 111.79(13) ?
C9 C7 P1 . . 113.20(13) ?
C8 C7 P1 . . 104.50(13) ?
C13 C11 C12 . . 109.71(16) ?
C13 C11 C14 . . 108.60(17) ?
C12 C11 C14 . . 108.90(16) ?
C13 C11 P1 . . 111.52(13) ?
C12 C11 P1 . . 112.97(13) ?
C14 C11 P1 . . 104.92(13) ?
C18 C15 C17 . . 109.9(5) ?
C16A C15 C17A . . 112.4(9) ?
C18 C15 C16 . . 108.1(3) ?
C17 C15 C16 . . 107.0(5) ?
C16A C15 C18A . . 108.8(5) ?
C17A C15 C18A . . 108.4(7) ?
C16A C15 P2 . . 106.8(6) ?
C18 C15 P2 . . 113.3(3) ?
C17 C15 P2 . . 115.2(6) ?
C17A C15 P2 . . 111.4(10) ?
C16 C15 P2 . . 102.7(3) ?
C18A C15 P2 . . 109.0(5) ?
C22 C19 C21 . . 111.2(2) ?
C22 C19 C20 . . 108.5(3) ?
C21 C19 C20 . . 107.9(2) ?
C20A C19 C21A . . 112.8(5) ?
C20A C19 C22A . . 109.0(6) ?
C21A C19 C22A . . 104.1(4) ?
C20A C19 P2 . . 116.2(6) ?
C22 C19 P2 . . 106.5(2) ?
C21 C19 P2 . . 110.44(17) ?
C20 C19 P2 . . 112.3(2) ?
C21A C19 P2 . . 111.7(3) ?
C22A C19 P2 . . 101.6(4) ?
C6 O1 P1 . . 112.40(10) ?
C2 O2 P2 . . 112.39(11) ?
O1 P1 C11 . . 99.29(7) ?
O1 P1 C7 . . 100.17(8) ?
C11 P1 C7 . . 113.72(9) ?
O1 P1 Ni1 . . 106.05(5) ?
C11 P1 Ni1 . . 118.76(6) ?
C7 P1 Ni1 . . 115.11(6) ?
O2 P2 C15 . . 99.41(8) ?
O2 P2 C19 . . 99.73(7) ?
C15 P2 C19 . . 113.74(8) ?
O2 P2 Ni1 . . 105.76(5) ?
C15 P2 Ni1 . . 118.02(6) ?
C19 P2 Ni1 . . 116.23(6) ?

