# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_ni2
_database_code_depnum_ccdc_archive 'CCDC 1535923'
_audit_update_record             
;
2017-03-03 deposited with the CCDC.
2017-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H31 N Ni P, C F3 O3 S'
_chemical_formula_sum            'C26 H31 F3 N Ni O3 P S'
_chemical_formula_weight         584.26

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.4721(16)
_cell_length_b                   17.5103(17)
_cell_length_c                   18.5492(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5350.2(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9973
_cell_measurement_theta_min      2.733
_cell_measurement_theta_max      30.243

_exptl_crystal_description       block
_exptl_crystal_colour            yellow-orange
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2432
_exptl_absorpt_coefficient_mu    0.912
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Apex Duo'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            82719
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         30.38
_reflns_number_total             8069
_reflns_number_gt                6345
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART v5.625'
_computing_cell_refinement       'Bruker SAINT v8.34A'
_computing_data_reduction        'Bruker SAINT v8.34A'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0625P)²+0.7159P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8069
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.1051
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni 0.409634(11) 0.080046(11) 0.651646(10) 0.01853(6) Uani 1 1 d . . .
P P 0.34775(2) 0.01432(2) 0.73385(2) 0.01723(9) Uani 1 1 d . . .
N N 0.30603(8) 0.10843(7) 0.60973(7) 0.0179(2) Uani 1 1 d . . .
S S 0.01015(3) 0.23741(3) 0.58847(3) 0.03225(11) Uani 1 1 d . . .
F1 F -0.08397(11) 0.33954(9) 0.64892(7) 0.0671(5) Uani 1 1 d . . .
O1 O -0.05956(8) 0.21118(9) 0.54910(8) 0.0423(4) Uani 1 1 d . . .
C1 C 0.39704(9) -0.02863(9) 0.81116(8) 0.0200(3) Uani 1 1 d . . .
F2 F 0.02133(8) 0.31063(8) 0.71154(6) 0.0520(3) Uani 1 1 d . . .
O2 O 0.05935(10) 0.17840(10) 0.61983(10) 0.0566(5) Uani 1 1 d . . .
C2 C 0.45149(10) 0.01584(10) 0.85070(8) 0.0254(3) Uani 1 1 d . . .
H2B H 0.4602 0.0678 0.8381 0.030 Uiso 1 1 calc R . .
F3 F -0.07900(8) 0.23390(9) 0.70527(8) 0.0568(4) Uani 1 1 d . . .
O3 O 0.05409(12) 0.29784(12) 0.55440(8) 0.0629(5) Uani 1 1 d . . .
C3 C 0.49295(10) -0.01614(12) 0.90856(9) 0.0310(4) Uani 1 1 d . . .
H3B H 0.5301 0.0140 0.9354 0.037 Uiso 1 1 calc R . .
C4 C 0.48029(11) -0.09203(12) 0.92739(9) 0.0320(4) Uani 1 1 d . . .
H4A H 0.5093 -0.1138 0.9666 0.038 Uiso 1 1 calc R . .
C5 C 0.42559(11) -0.13565(10) 0.88910(9) 0.0286(4) Uani 1 1 d . . .
H5A H 0.4164 -0.1873 0.9025 0.034 Uiso 1 1 calc R . .
C6 C 0.38364(10) -0.10452(9) 0.83092(9) 0.0235(3) Uani 1 1 d . . .
H6A H 0.3460 -0.1349 0.8047 0.028 Uiso 1 1 calc R . .
C7 C 0.27848(9) -0.05665(9) 0.69830(8) 0.0200(3) Uani 1 1 d . . .
C8 C 0.30871(11) -0.10605(9) 0.64578(9) 0.0250(3) Uani 1 1 d . . .
H8A H 0.3644 -0.1040 0.6327 0.030 Uiso 1 1 calc R . .
C9 C 0.25743(13) -0.15825(10) 0.61250(11) 0.0346(4) Uani 1 1 d . . .
H9A H 0.2780 -0.1917 0.5766 0.042 Uiso 1 1 calc R . .
C10 C 0.17641(13) -0.16151(11) 0.63165(11) 0.0383(4) Uani 1 1 d . . .
H10A H 0.1414 -0.1970 0.6085 0.046 Uiso 1 1 calc R . .
C11 C 0.14610(11) -0.11341(11) 0.68428(11) 0.0348(4) Uani 1 1 d . . .
H11A H 0.0904 -0.1162 0.6974 0.042 Uiso 1 1 calc R . .
C12 C 0.19683(10) -0.06087(10) 0.71806(9) 0.0274(3) Uani 1 1 d . . .
H12A H 0.1760 -0.0280 0.7544 0.033 Uiso 1 1 calc R . .
C13 C 0.28629(9) 0.09166(8) 0.77010(8) 0.0195(3) Uani 1 1 d . . .
C14 C 0.26623(12) 0.10650(11) 0.84838(8) 0.0286(4) Uani 1 1 d . . .
H14A H 0.3159 0.1064 0.8784 0.034 Uiso 1 1 calc R . .
H14B H 0.2280 0.0677 0.8672 0.034 Uiso 1 1 calc R . .
C15 C 0.22685(12) 0.18607(11) 0.84709(9) 0.0300(4) Uani 1 1 d . . .
H15A H 0.2656 0.2251 0.8646 0.036 Uiso 1 1 calc R . .
H15B H 0.1781 0.1871 0.8782 0.036 Uiso 1 1 calc R . .
C16 C 0.20351(11) 0.20178(10) 0.76820(9) 0.0299(4) Uani 1 1 d . . .
H16A H 0.1446 0.1944 0.7605 0.036 Uiso 1 1 calc R . .
H16B H 0.2184 0.2544 0.7539 0.036 Uiso 1 1 calc R . .
C17 C 0.25216(9) 0.14377(9) 0.72672(8) 0.0201(3) Uani 1 1 d . . .
C18 C 0.24902(9) 0.13854(9) 0.64791(8) 0.0204(3) Uani 1 1 d . . .
H18A H 0.2027 0.1583 0.6238 0.025 Uiso 1 1 calc R . .
C19 C 0.28731(9) 0.09306(9) 0.53075(8) 0.0207(3) Uani 1 1 d . . .
C20 C 0.21081(10) 0.04388(10) 0.52563(9) 0.0275(3) Uani 1 1 d . . .
H20A H 0.2196 -0.0043 0.5513 0.041 Uiso 1 1 calc R . .
H20B H 0.1988 0.0332 0.4749 0.041 Uiso 1 1 calc R . .
H20C H 0.1650 0.0712 0.5474 0.041 Uiso 1 1 calc R . .
C21 C 0.27497(12) 0.16878(10) 0.49112(9) 0.0295(4) Uani 1 1 d . . .
H21A H 0.3244 0.1996 0.4949 0.044 Uiso 1 1 calc R . .
H21B H 0.2295 0.1965 0.5129 0.044 Uiso 1 1 calc R . .
H21C H 0.2631 0.1587 0.4402 0.044 Uiso 1 1 calc R . .
C22 C 0.35892(11) 0.04992(12) 0.49844(9) 0.0321(4) Uani 1 1 d . . .
H22A H 0.3664 0.0016 0.5242 0.048 Uiso 1 1 calc R . .
H22B H 0.4082 0.0809 0.5029 0.048 Uiso 1 1 calc R . .
H22C H 0.3482 0.0395 0.4474 0.048 Uiso 1 1 calc R . .
C23 C 0.48038(12) 0.16768(12) 0.61059(11) 0.0386(5) Uani 1 1 d . . .
H23A H 0.4690 0.1841 0.5605 0.046 Uiso 1 1 calc R . .
H23B H 0.4936 0.2102 0.6437 0.046 Uiso 1 1 calc R . .
C24 C 0.52281(12) 0.10235(15) 0.61901(13) 0.0447(5) Uani 1 1 d . . .
H24A H 0.5440 0.0758 0.5752 0.054 Uiso 1 1 calc R . .
C25 C 0.52257(10) 0.06290(14) 0.68519(11) 0.0396(5) Uani 1 1 d . . .
H25A H 0.5401 0.0920 0.7282 0.048 Uiso 1 1 calc R . .
H25B H 0.5425 0.0096 0.6844 0.048 Uiso 1 1 calc R . .
C26 C -0.03463(12) 0.28283(11) 0.66699(10) 0.0332(4) 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
Ni N 1.9400(13) . ?
Ni C25 1.9845(18) . ?
Ni C24 1.9986(19) . ?
Ni C23 2.0719(18) . ?
Ni P 2.1653(4) . ?
P C7 1.8114(16) . ?
P C1 1.8114(15) . ?
P C13 1.8196(15) . ?
N C18 1.2890(19) . ?
N C19 1.5212(19) . ?
S O3 1.4293(17) . ?
S O1 1.4362(14) . ?
S O2 1.4361(17) . ?
S C26 1.816(2) . ?
F1 C26 1.326(2) . ?
C1 C6 1.396(2) . ?
C1 C2 1.396(2) . ?
F2 C26 1.330(2) . ?
C2 C3 1.390(2) . ?
F3 C26 1.331(2) . ?
C3 C4 1.390(3) . ?
C4 C5 1.378(3) . ?
C5 C6 1.392(2) . ?
C7 C8 1.395(2) . ?
C7 C12 1.396(2) . ?
C8 C9 1.389(2) . ?
C9 C10 1.382(3) . ?
C10 C11 1.383(3) . ?
C11 C12 1.392(2) . ?
C13 C17 1.340(2) . ?
C13 C14 1.512(2) . ?
C14 C15 1.537(3) . ?
C15 C16 1.538(2) . ?
C16 C17 1.505(2) . ?
C17 C18 1.466(2) . ?
C19 C22 1.523(2) . ?
C19 C20 1.529(2) . ?
C19 C21 1.530(2) . ?
C23 C24 1.350(3) . ?
C24 C25 1.409(3) . ?

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
N Ni C25 171.50(7) . . ?
N Ni C24 130.47(8) . . ?
C25 Ni C24 41.42(9) . . ?
N Ni C23 99.08(7) . . ?
C25 Ni C23 72.54(9) . . ?
C24 Ni C23 38.67(9) . . ?
N Ni P 90.24(4) . . ?
C25 Ni P 98.05(6) . . ?
C24 Ni P 139.14(7) . . ?
C23 Ni P 156.53(6) . . ?
C7 P C1 106.60(7) . . ?
C7 P C13 107.14(7) . . ?
C1 P C13 105.42(7) . . ?
C7 P Ni 113.88(5) . . ?
C1 P Ni 124.55(5) . . ?
C13 P Ni 97.27(5) . . ?
C18 N C19 116.98(12) . . ?
C18 N Ni 121.71(11) . . ?
C19 N Ni 121.26(10) . . ?
O3 S O1 114.63(10) . . ?
O3 S O2 115.21(12) . . ?
O1 S O2 115.28(10) . . ?
O3 S C26 103.65(10) . . ?
O1 S C26 102.89(8) . . ?
O2 S C26 102.68(10) . . ?
C6 C1 C2 119.64(14) . . ?
C6 C1 P 122.15(12) . . ?
C2 C1 P 118.19(12) . . ?
C3 C2 C1 119.78(16) . . ?
C4 C3 C2 120.38(17) . . ?
C5 C4 C3 119.89(16) . . ?
C4 C5 C6 120.46(17) . . ?
C5 C6 C1 119.84(16) . . ?
C8 C7 C12 119.64(15) . . ?
C8 C7 P 117.06(12) . . ?
C12 C7 P 123.20(13) . . ?
C9 C8 C7 120.09(17) . . ?
C10 C9 C8 120.01(18) . . ?
C9 C10 C11 120.33(17) . . ?
C10 C11 C12 120.25(18) . . ?
C11 C12 C7 119.68(17) . . ?
C17 C13 C14 111.59(14) . . ?
C17 C13 P 121.22(12) . . ?
C14 C13 P 127.19(12) . . ?
C13 C14 C15 103.48(14) . . ?
C14 C15 C16 106.41(13) . . ?
C17 C16 C15 103.45(14) . . ?
C13 C17 C18 124.82(14) . . ?
C13 C17 C16 112.08(14) . . ?
C18 C17 C16 122.22(14) . . ?
N C18 C17 123.21(14) . . ?
N C19 C22 108.04(12) . . ?
N C19 C20 109.05(13) . . ?
C22 C19 C20 109.53(14) . . ?
N C19 C21 109.67(13) . . ?
C22 C19 C21 110.10(14) . . ?
C20 C19 C21 110.41(13) . . ?
C24 C23 Ni 67.73(12) . . ?
C23 C24 C25 121.0(2) . . ?
C23 C24 Ni 73.60(12) . . ?
C25 C24 Ni 68.75(11) . . ?
C24 C25 Ni 69.83(11) . . ?
F1 C26 F2 107.91(17) . . ?
F1 C26 F3 106.28(17) . . ?
F2 C26 F3 106.53(16) . . ?
F1 C26 S 111.98(13) . . ?
F2 C26 S 112.15(14) . . ?
F3 C26 S 111.65(14) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.38
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.032
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.076
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pentane, THF'
_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
