# Electronic Supplementary Material (ESI) for ChemComm.
# 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_sz318benzene
_database_code_depnum_ccdc_archive 'CCDC 1580329'
_audit_update_record             
;
2017-10-16 deposited with the CCDC.
2017-11-21 downloaded from the CCDC.
;

_audit_creation_date             2017-10-11T11:10:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C24  H39 Ni P'
_chemical_formula_sum            'C24 H39 Ni P'
_chemical_formula_weight         417.23
_chemical_compound_source        synthesized

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.8511(11)
_cell_length_b                   22.745(2)
_cell_length_c                   9.8693(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.166(2)
_cell_angle_gamma                90
_cell_volume                     2209.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    9470
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      34.66
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction'
_exptl_absorpt_correction_T_min  0.7834
_exptl_absorpt_correction_T_max  0.8625
_shelx_estimated_absorpt_T_min   0.75
_shelx_estimated_absorpt_T_max   0.825

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_number            72724
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.005
_diffrn_reflns_theta_max         34.999
_diffrn_reflns_theta_full        34.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             9693
_reflns_number_gt                8107
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0276P)²+0.3753P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         9693
_refine_ls_number_parameters     291
_refine_ls_number_restraints     12
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0666
_refine_ls_wR_factor_gt          0.0624
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.052

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.74325(2) 0.20377(2) 0.70595(2) 0.01834(4) Uani 0.9498(8) 1 d . . P A 1
P1 P 0.81298(5) 0.12496(2) 0.61847(8) 0.01486(8) Uani 0.9498(8) 1 d . . P A 1
C1 C 0.82481(15) 0.28047(6) 0.80009(16) 0.0319(3) Uani 0.9498(8) 1 d . . P A 1
H1 H 0.915812 0.292018 0.82137 0.038 Uiso 0.9498(8) 1 calc R U P A 1
C2 C 0.75202(16) 0.24844(6) 0.89449(14) 0.0330(3) Uani 0.9498(8) 1 d . . P A 1
H2 H 0.793862 0.238245 0.979567 0.04 Uiso 0.9498(8) 1 calc R U P A 1
C3 C 0.61719(16) 0.23133(6) 0.86362(18) 0.0363(3) Uani 0.9498(8) 1 d . . P A 1
H3 H 0.567926 0.209822 0.928039 0.044 Uiso 0.9498(8) 1 calc R U P A 1
C4 C 0.55565(15) 0.24595(7) 0.7383(2) 0.0377(3) Uani 0.9498(8) 1 d . . P A 1
H4 H 0.464747 0.234181 0.717299 0.045 Uiso 0.9498(8) 1 calc R U P A 1
C5 C 0.62821(16) 0.27810(6) 0.64308(17) 0.0367(3) Uani 0.9498(8) 1 d . . P A 1
H5 H 0.586171 0.288066 0.55795 0.044 Uiso 0.9498(8) 1 calc R U P A 1
C6 C 0.76334(17) 0.29555(5) 0.67381(18) 0.0327(3) Uani 0.9498(8) 1 d . . P A 1
H6 H 0.812457 0.317332 0.609735 0.039 Uiso 0.9498(8) 1 calc R U P A 1
C7 C 0.82281(10) 0.12952(4) 0.43138(10) 0.01773(17) Uani 1 1 d D . . A 1
H7 H 0.889501 0.161539 0.413986 0.021 Uiso 1 1 calc R U . A 1
C8 C 0.87360(12) 0.07543(5) 0.35504(12) 0.0242(2) Uani 1 1 d D . . A 1
H8A H 0.96145 0.062278 0.396636 0.029 Uiso 1 1 calc R U . A 1
H8B H 0.807496 0.04291 0.36253 0.029 Uiso 1 1 calc R U . A 1
C9 C 0.89158(12) 0.09000(6) 0.20542(12) 0.0282(2) Uani 1 1 d D . . A 1
H9A H 0.963009 0.12032 0.197893 0.034 Uiso 1 1 calc R U . A 1
H9B H 0.921548 0.054344 0.157408 0.034 Uiso 1 1 calc R U . A 1
C10 C 0.75958(13) 0.11242(6) 0.13853(12) 0.0304(2) Uani 1 1 d D . . A 1
H10A H 0.692142 0.080137 0.134425 0.036 Uiso 1 1 calc R U . A 1
H10B H 0.776495 0.124735 0.044443 0.036 Uiso 1 1 calc R U . A 1
C11 C 0.70147(12) 0.16439(6) 0.21611(12) 0.0295(2) Uani 1 1 d D . . A 1
H11A H 0.761929 0.198828 0.207227 0.035 Uiso 1 1 calc R U . A 1
H11B H 0.61131 0.174843 0.175362 0.035 Uiso 1 1 calc R U . A 1
C12 C 0.68699(11) 0.15039(5) 0.36650(11) 0.0245(2) Uani 1 1 d D . . A 1
H12A H 0.617562 0.119363 0.376295 0.029 Uiso 1 1 calc R U . A 1
H12B H 0.656057 0.185957 0.414223 0.029 Uiso 1 1 calc R U . A 1
C13 C 0.98988(9) 0.10279(5) 0.67373(11) 0.01881(18) Uani 1 1 d . . . A 1
H13 H 1.007602 0.062209 0.639628 0.023 Uiso 1 1 calc R U . A 1
C14 C 1.09542(10) 0.14498(5) 0.61624(12) 0.0251(2) Uani 1 1 d . . . A 1
H14A H 1.091946 0.142277 0.516051 0.03 Uiso 1 1 calc R U . A 1
H14B H 1.072731 0.185855 0.641357 0.03 Uiso 1 1 calc R U . A 1
C15 C 1.23962(11) 0.13032(6) 0.67047(13) 0.0307(3) Uani 1 1 d . . . A 1
H15A H 1.265166 0.090631 0.639081 0.037 Uiso 1 1 calc R U . A 1
H15B H 1.30452 0.158902 0.633759 0.037 Uiso 1 1 calc R U . A 1
C16 C 1.24904(12) 0.13218(6) 0.82410(14) 0.0331(3) Uani 1 1 d . . . A 1
H16A H 1.230151 0.17258 0.855616 0.04 Uiso 1 1 calc R U . A 1
H16B H 1.342166 0.121449 0.856288 0.04 Uiso 1 1 calc R U . A 1
C17 C 1.14714(12) 0.08954(6) 0.88332(13) 0.0302(2) Uani 1 1 d . . . A 1
H17A H 1.150771 0.092978 0.983384 0.036 Uiso 1 1 calc R U . A 1
H17B H 1.172135 0.048748 0.859687 0.036 Uiso 1 1 calc R U . A 1
C18 C 1.00202(11) 0.10235(5) 0.82890(11) 0.0246(2) Uani 1 1 d . . . A 1
H18A H 0.939925 0.072156 0.863758 0.03 Uiso 1 1 calc R U . A 1
H18B H 0.972903 0.141028 0.863465 0.03 Uiso 1 1 calc R U . A 1
C19 C 0.70692(12) 0.05746(6) 0.64245(15) 0.0173(2) Uani 0.9498(8) 1 d . . P A 1
H19 H 0.641477 0.055596 0.562598 0.021 Uiso 0.9498(8) 1 calc R U P A 1
C20 C 0.78222(11) -0.00192(5) 0.64688(13) 0.0226(2) Uani 0.9498(8) 1 d . . P A
1
H20A H 0.831045 -0.007057 0.561826 0.027 Uiso 0.9498(8) 1 calc R U P A 1
H20B H 0.850511 -0.001623 0.72309 0.027 Uiso 0.9498(8) 1 calc R U P A 1
C21 C 0.6853(2) -0.05386(6) 0.66425(18) 0.0291(4) Uani 0.9498(8) 1 d . . P A 1
H21A H 0.622538 -0.05665 0.583798 0.035 Uiso 0.9498(8) 1 calc R U P A 1
H21B H 0.738331 -0.090808 0.670723 0.035 Uiso 0.9498(8) 1 calc R U P A 1
C22 C 0.60370(12) -0.04664(5) 0.79098(13) 0.0271(2) Uani 0.9498(8) 1 d . . P A
1
H22A H 0.66585 -0.046964 0.872184 0.033 Uiso 0.9498(8) 1 calc R U P A 1
H22B H 0.53977 -0.079968 0.798299 0.033 Uiso 0.9498(8) 1 calc R U P A 1
C23 C 0.52467(19) 0.01089(7) 0.7855(2) 0.0278(3) Uani 0.9498(8) 1 d . . P A 1
H23A H 0.47468 0.015565 0.870025 0.033 Uiso 0.9498(8) 1 calc R U P A 1
H23B H 0.45736 0.009813 0.708504 0.033 Uiso 0.9498(8) 1 calc R U P A 1
C24 C 0.62018(12) 0.06355(5) 0.76891(13) 0.0252(2) Uani 0.9498(8) 1 d . . P A 1
H24A H 0.681073 0.066946 0.850653 0.03 Uiso 0.9498(8) 1 calc R U P A 1
H24B H 0.565613 0.100027 0.761253 0.03 Uiso 0.9498(8) 1 calc R U P A 1
NI1B Ni 0.7107(4) 0.0373(2) 0.6807(5) 0.0322(11) Uani 0.0502(8) 1 d . . P A 2
C1B C 0.7482(19) -0.0423(11) 0.787(2) 0.058(8) Uiso 0.0502(8) 1 d G . P A 2
H1B H 0.830084 -0.058112 0.826118 0.069 Uiso 0.0502(8) 1 calc R U P A 2
C2B C 0.666(2) -0.0070(10) 0.8648(17) 0.037(6) Uiso 0.0502(8) 1 d G . P A 2
H2B H 0.691714 0.001316 0.956581 0.045 Uiso 0.0502(8) 1 calc R U P A 2
C3B C 0.546(2) 0.0161(10) 0.808(2) 0.027(10) Uiso 0.0502(8) 1 d G . P A 2
H3B H 0.49006 0.040204 0.861071 0.032 Uiso 0.0502(8) 1 calc R U P A 2
C4B C 0.5086(18) 0.0039(10) 0.674(2) 0.043(7) Uiso 0.0502(8) 1 d G . P A 2
H4B H 0.426775 0.019665 0.635098 0.052 Uiso 0.0502(8) 1 calc R U P A 2
C5B C 0.591(2) -0.0314(10) 0.5964(17) 0.040(6) Uiso 0.0502(8) 1 d G . P A 2
H5B H 0.565143 -0.039763 0.504634 0.048 Uiso 0.0502(8) 1 calc R U P A 2
C6B C 0.711(2) -0.0545(11) 0.653(2) 0.033(12) Uiso 0.0502(8) 1 d G . P A 2
H6B H 0.766798 -0.078652 0.600141 0.04 Uiso 0.0502(8) 1 calc R U P A 2
P1B P 0.8211(19) 0.1101(7) 0.6262(18) 0.043(4) Uani 0.0502(8) 1 d . . P A 2
C19B C 0.778(3) 0.1741(10) 0.686(3) 0.043(6) Uiso 0.0502(8) 1 d D . P A 2
H19B H 0.828955 0.174041 0.776112 0.051 Uiso 0.0502(8) 1 calc R U P A 2
C20B C 0.819(3) 0.2347(10) 0.630(3) 0.049(7) Uiso 0.0502(8) 1 d D . P A 2
H20C H 0.768839 0.241214 0.542378 0.059 Uiso 0.0502(8) 1 calc R U P A 2
H20D H 0.917315 0.233727 0.611013 0.059 Uiso 0.0502(8) 1 calc R U P A 2
C21B C 0.792(2) 0.2874(10) 0.725(3) 0.028(5) Uiso 0.0502(8) 1 d D . P A 2
H21C H 0.831199 0.279657 0.817351 0.033 Uiso 0.0502(8) 1 calc R U P A 2
H21D H 0.833816 0.323747 0.690007 0.033 Uiso 0.0502(8) 1 calc R U P A 2
C22B C 0.636(2) 0.2939(11) 0.728(4) 0.049(8) Uiso 0.0502(8) 1 d D . P A 2
H22C H 0.611145 0.329128 0.780123 0.059 Uiso 0.0502(8) 1 calc R U P A 2
H22D H 0.596057 0.297243 0.63469 0.059 Uiso 0.0502(8) 1 calc R U P A 2
C23B C 0.587(3) 0.2384(9) 0.796(3) 0.025(5) Uiso 0.0502(8) 1 d D . P A 2
H23C H 0.621132 0.238567 0.891674 0.03 Uiso 0.0502(8) 1 calc R U P A 2
H23D H 0.486734 0.239289 0.79603 0.03 Uiso 0.0502(8) 1 calc R U P A 2
C24B C 0.631(3) 0.1815(11) 0.731(4) 0.060(9) Uiso 0.0502(8) 1 d D . P A 2
H24C H 0.569969 0.174931 0.650279 0.072 Uiso 0.0502(8) 1 calc R U P A 2
H24D H 0.612472 0.149366 0.795804 0.072 Uiso 0.0502(8) 1 calc R U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C5 2.1152(13) . ?
NI1 P1 2.1154(6) . ?
NI1 C4 2.1171(13) . ?
NI1 C2 2.1190(13) . ?
NI1 C1 2.1204(13) . ?
NI1 C3 2.1220(13) . ?
NI1 C6 2.1220(13) . ?
P1 C7 1.8556(13) . ?
P1 C13 1.8753(11) . ?
P1 C19 1.8771(15) . ?
C1 C2 1.401(2) . ?
C1 C6 1.407(2) . ?
C1 H1 0.95 . ?
C2 C3 1.406(2) . ?
C2 H2 0.95 . ?
C3 C4 1.397(2) . ?
C3 H3 0.95 . ?
C4 C5 1.407(2) . ?
C4 H4 0.95 . ?
C5 C6 1.411(2) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.5362(14) . ?
C7 C12 1.5364(14) . ?
C7 H7 1 . ?
C8 C9 1.5302(16) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C10 1.5237(18) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.5311(18) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C12 1.5300(16) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 C18 1.5316(15) . ?
C13 C14 1.5389(14) . ?
C13 H13 1 . ?
C14 C15 1.5355(16) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C15 C16 1.5162(19) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 C17 1.5279(19) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 C18 1.5359(15) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
C19 C20 1.5406(16) . ?
C19 C24 1.5452(17) . ?
C19 H19 1 . ?
C20 C21 1.533(2) . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?
C21 C22 1.521(2) . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
C22 C23 1.5225(19) . ?
C22 H22A 0.99 . ?
C22 H22B 0.99 . ?
C23 C24 1.536(2) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
NI1B P1B 2.064(17) . ?
NI1B C6B 2.11(2) . ?
NI1B C5B 2.11(2) . ?
NI1B C1B 2.12(2) . ?
NI1B C4B 2.13(2) . ?
NI1B C2B 2.14(2) . ?
NI1B C3B 2.14(2) . ?
C1B C2B 1.39 . ?
C1B C6B 1.39 . ?
C1B H1B 0.95 . ?
C2B C3B 1.39 . ?
C2B H2B 0.95 . ?
C3B C4B 1.39 . ?
C3B H3B 0.95 . ?
C4B C5B 1.39 . ?
C4B H4B 0.95 . ?
C5B C6B 1.39 . ?
C5B H5B 0.95 . ?
C6B H6B 0.95 . ?
P1B C19B 1.63(3) . ?
C19B C24B 1.544(18) . ?
C19B C20B 1.547(18) . ?
C19B H19B 1 . ?
C20B C21B 1.554(18) . ?
C20B H20C 0.99 . ?
C20B H20D 0.99 . ?
C21B C22B 1.547(18) . ?
C21B H21C 0.99 . ?
C21B H21D 0.99 . ?
C22B C23B 1.518(18) . ?
C22B H22C 0.99 . ?
C22B H22D 0.99 . ?
C23B C24B 1.512(18) . ?
C23B H23C 0.99 . ?
C23B H23D 0.99 . ?
C24B H24C 0.99 . ?
C24B H24D 0.99 . ?

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 NI1 P1 137.41(5) . . ?
C5 NI1 C4 38.82(7) . . ?
P1 NI1 C4 138.10(5) . . ?
C5 NI1 C2 82.99(6) . . ?
P1 NI1 C2 139.60(4) . . ?
C4 NI1 C2 69.95(7) . . ?
C5 NI1 C1 70.18(6) . . ?
P1 NI1 C1 138.81(4) . . ?
C4 NI1 C1 83.08(6) . . ?
C2 NI1 C1 38.60(6) . . ?
C5 NI1 C3 69.94(7) . . ?
P1 NI1 C3 139.26(4) . . ?
C4 NI1 C3 38.49(7) . . ?
C2 NI1 C3 38.73(6) . . ?
C1 NI1 C3 70.01(6) . . ?
C5 NI1 C6 38.90(6) . . ?
P1 NI1 C6 137.65(5) . . ?
C4 NI1 C6 70.33(6) . . ?
C2 NI1 C6 70.04(6) . . ?
C1 NI1 C6 38.75(6) . . ?
C3 NI1 C6 83.07(6) . . ?
C7 P1 C13 102.80(5) . . ?
C7 P1 C19 102.79(6) . . ?
C13 P1 C19 105.01(6) . . ?
C7 P1 NI1 112.87(4) . . ?
C13 P1 NI1 114.94(5) . . ?
C19 P1 NI1 116.79(5) . . ?
C2 C1 C6 120.11(13) . . ?
C2 C1 NI1 70.65(7) . . ?
C6 C1 NI1 70.69(7) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
NI1 C1 H1 131.5 . . ?
C1 C2 C3 120.18(14) . . ?
C1 C2 NI1 70.75(8) . . ?
C3 C2 NI1 70.75(8) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
NI1 C2 H2 131.4 . . ?
C4 C3 C2 120.04(13) . . ?
C4 C3 NI1 70.57(8) . . ?
C2 C3 NI1 70.52(7) . . ?
C4 C3 H3 120 . . ?
C2 C3 H3 120 . . ?
NI1 C3 H3 131.8 . . ?
C3 C4 C5 120.04(14) . . ?
C3 C4 NI1 70.94(8) . . ?
C5 C4 NI1 70.52(8) . . ?
C3 C4 H4 120 . . ?
C5 C4 H4 120 . . ?
NI1 C4 H4 131.3 . . ?
C4 C5 C6 120.12(14) . . ?
C4 C5 NI1 70.66(8) . . ?
C6 C5 NI1 70.81(8) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
NI1 C5 H5 131.4 . . ?
C1 C6 C5 119.51(13) . . ?
C1 C6 NI1 70.56(8) . . ?
C5 C6 NI1 70.29(7) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
NI1 C6 H6 131.7 . . ?
C8 C7 C12 109.73(9) . . ?
C8 C7 P1 118.26(8) . . ?
C12 C7 P1 110.77(7) . . ?
C8 C7 H7 105.7 . . ?
C12 C7 H7 105.7 . . ?
P1 C7 H7 105.7 . . ?
C9 C8 C7 110.58(9) . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C8 111.26(9) . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108 . . ?
C9 C10 C11 111.76(10) . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C10 112.01(11) . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C7 110.91(9) . . ?
C11 C12 H12A 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 108 . . ?
C18 C13 C14 110.14(9) . . ?
C18 C13 P1 109.22(7) . . ?
C14 C13 P1 111.01(7) . . ?
C18 C13 H13 108.8 . . ?
C14 C13 H13 108.8 . . ?
P1 C13 H13 108.8 . . ?
C15 C14 C13 111.42(10) . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108 . . ?
C16 C15 C14 111.30(10) . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108 . . ?
C15 C16 C17 110.40(10) . . ?
C15 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C16 C17 C18 111.23(10) . . ?
C16 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108 . . ?
C13 C18 C17 112.79(9) . . ?
C13 C18 H18A 109 . . ?
C17 C18 H18A 109 . . ?
C13 C18 H18B 109 . . ?
C17 C18 H18B 109 . . ?
H18A C18 H18B 107.8 . . ?
C20 C19 C24 109.63(11) . . ?
C20 C19 P1 116.79(8) . . ?
C24 C19 P1 110.85(9) . . ?
C20 C19 H19 106.3 . . ?
C24 C19 H19 106.3 . . ?
P1 C19 H19 106.3 . . ?
C21 C20 C19 112.19(11) . . ?
C21 C20 H20A 109.2 . . ?
C19 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
C19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C22 C21 C20 111.07(11) . . ?
C22 C21 H21A 109.4 . . ?
C20 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C20 C21 H21B 109.4 . . ?
H21A C21 H21B 108 . . ?
C21 C22 C23 110.45(11) . . ?
C21 C22 H22A 109.6 . . ?
C23 C22 H22A 109.6 . . ?
C21 C22 H22B 109.6 . . ?
C23 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
C22 C23 C24 111.06(12) . . ?
C22 C23 H23A 109.4 . . ?
C24 C23 H23A 109.4 . . ?
C22 C23 H23B 109.4 . . ?
C24 C23 H23B 109.4 . . ?
H23A C23 H23B 108 . . ?
C23 C24 C19 112.10(11) . . ?
C23 C24 H24A 109.2 . . ?
C19 C24 H24A 109.2 . . ?
C23 C24 H24B 109.2 . . ?
C19 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
P1B NI1B C6B 139.4(8) . . ?
P1B NI1B C5B 141.6(8) . . ?
C6B NI1B C5B 38.5(4) . . ?
P1B NI1B C1B 137.0(8) . . ?
C6B NI1B C1B 38.4(4) . . ?
C5B NI1B C1B 69.3(6) . . ?
P1B NI1B C4B 141.2(8) . . ?
C6B NI1B C4B 69.3(5) . . ?
C5B NI1B C4B 38.3(3) . . ?
C1B NI1B C4B 81.7(5) . . ?
P1B NI1B C2B 136.7(7) . . ?
C6B NI1B C2B 69.1(6) . . ?
C5B NI1B C2B 81.7(5) . . ?
C1B NI1B C2B 38.1(4) . . ?
C4B NI1B C2B 68.7(5) . . ?
P1B NI1B C3B 138.7(8) . . ?
C6B NI1B C3B 81.7(5) . . ?
C5B NI1B C3B 68.9(5) . . ?
C1B NI1B C3B 68.8(5) . . ?
C4B NI1B C3B 38.0(4) . . ?
C2B NI1B C3B 37.9(4) . . ?
C2B C1B C6B 120 . . ?
C2B C1B NI1B 71.7(8) . . ?
C6B C1B NI1B 70.3(7) . . ?
C2B C1B H1B 120 . . ?
C6B C1B H1B 120 . . ?
NI1B C1B H1B 130.7 . . ?
C1B C2B C3B 120 . . ?
C1B C2B NI1B 70.3(9) . . ?
C3B C2B NI1B 71.2(8) . . ?
C1B C2B H2B 120 . . ?
C3B C2B H2B 120 . . ?
NI1B C2B H2B 131.3 . . ?
C4B C3B C2B 120 . . ?
C4B C3B NI1B 70.5(7) . . ?
C2B C3B NI1B 70.9(7) . . ?
C4B C3B H3B 120 . . ?
C2B C3B H3B 120 . . ?
NI1B C3B H3B 131.4 . . ?
C3B C4B C5B 120 . . ?
C3B C4B NI1B 71.5(7) . . ?
C5B C4B NI1B 70.2(8) . . ?
C3B C4B H4B 120 . . ?
C5B C4B H4B 120 . . ?
NI1B C4B H4B 131 . . ?
C6B C5B C4B 120 . . ?
C6B C5B NI1B 70.6(8) . . ?
C4B C5B NI1B 71.6(8) . . ?
C6B C5B H5B 120 . . ?
C4B C5B H5B 120 . . ?
NI1B C5B H5B 130.4 . . ?
C5B C6B C1B 120 . . ?
C5B C6B NI1B 70.9(7) . . ?
C1B C6B NI1B 71.3(7) . . ?
C5B C6B H6B 120 . . ?
C1B C6B H6B 120 . . ?
NI1B C6B H6B 130.3 . . ?
C19B P1B NI1B 118.2(13) . . ?
C24B C19B C20B 105.6(17) . . ?
C24B C19B P1B 117.4(18) . . ?
C20B C19B P1B 125.9(19) . . ?
C24B C19B H19B 101.1 . . ?
C20B C19B H19B 101.1 . . ?
P1B C19B H19B 101.1 . . ?
C19B C20B C21B 114.5(19) . . ?
C19B C20B H20C 108.6 . . ?
C21B C20B H20C 108.6 . . ?
C19B C20B H20D 108.6 . . ?
C21B C20B H20D 108.6 . . ?
H20C C20B H20D 107.6 . . ?
C22B C21B C20B 106.1(19) . . ?
C22B C21B H21C 110.5 . . ?
C20B C21B H21C 110.5 . . ?
C22B C21B H21D 110.5 . . ?
C20B C21B H21D 110.5 . . ?
H21C C21B H21D 108.7 . . ?
C23B C22B C21B 105.2(17) . . ?
C23B C22B H22C 110.7 . . ?
C21B C22B H22C 110.7 . . ?
C23B C22B H22D 110.7 . . ?
C21B C22B H22D 110.7 . . ?
H22C C22B H22D 108.8 . . ?
C24B C23B C22B 115(2) . . ?
C24B C23B H23C 108.5 . . ?
C22B C23B H23C 108.5 . . ?
C24B C23B H23D 108.5 . . ?
C22B C23B H23D 108.5 . . ?
H23C C23B H23D 107.5 . . ?
C23B C24B C19B 119.8(19) . . ?
C23B C24B H24C 107.4 . . ?
C19B C24B H24C 107.4 . . ?
C23B C24B H24D 107.4 . . ?
C19B C24B H24D 107.4 . . ?
H24C C24B H24D 106.9 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1580333'
_audit_update_record             
;
2017-10-16 deposited with the CCDC.
2017-11-21 downloaded from the CCDC.
;

_audit_creation_date             2016-10-12T07:19:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C27  H45  Ni P'
_chemical_formula_sum            'C27 H45 Ni P'
_chemical_formula_weight         459.31
_chemical_compound_source        synthesized

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.7379(14)
_cell_length_b                   9.3650(11)
_cell_length_c                   21.990(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.542(2)
_cell_angle_gamma                90
_cell_volume                     2539.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9935
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      29.94
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS - Bruker AXS  - Version 2012/1'
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.89

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_unetI/netI     0.038
_diffrn_reflns_number            6405
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.897
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        27.499
_diffrn_measured_fraction_theta_full 0.94
_diffrn_measured_fraction_theta_max 0.94
_diffrn_reflns_Laue_measured_fraction_full 0.94
_diffrn_reflns_Laue_measured_fraction_max 0.94
_diffrn_reflns_point_group_measured_fraction_full 0.94
_diffrn_reflns_point_group_measured_fraction_max 0.94
_reflns_Friedel_coverage         0
_reflns_number_total             6405
_reflns_number_gt                5207
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   iterative
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refined as a 2-component twin.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0057P)²+13.4060P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6405
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1453
_refine_ls_wR_factor_gt          0.1351
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.144
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.077



#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.76771(6) 0.98793(7) 0.06698(3) 0.02568(17) Uani 1 1 d . . . . .
P1 P 0.78465(11) 0.77866(12) 0.10273(6) 0.0183(3) Uani 1 1 d . . . . .
C1 C 0.8668(5) 1.1747(6) 0.0693(3) 0.0352(14) Uani 1 1 d . . . . .
C2 C 0.8327(6) 1.1228(6) 0.0075(3) 0.0444(17) Uani 1 1 d . . . . .
H2 H 0.885229 1.105161 -0.015509 0.053 Uiso 1 1 calc R U . . .
C3 C 0.7228(6) 1.0964(6) -0.0210(3) 0.0478(18) Uani 1 1 d . . . . .
C4 C 0.6448(5) 1.1216(6) 0.0132(3) 0.0426(16) Uani 1 1 d . . . . .
H4 H 0.570348 1.103948 -0.005848 0.051 Uiso 1 1 calc R U . . .
C5 C 0.6764(5) 1.1732(6) 0.0759(3) 0.0352(14) Uani 1 1 d . . . . .
C6 C 0.7873(5) 1.2002(5) 0.1029(3) 0.0305(12) Uani 1 1 d . . . . .
H6 H 0.809053 1.236419 0.14451 0.037 Uiso 1 1 calc R U . . .
C7 C 0.9835(5) 1.2083(7) 0.0980(3) 0.0519(18) Uani 1 1 d . . . . .
H7A H 1.029394 1.140542 0.08244 0.078 Uiso 1 1 calc R U . . .
H7B H 0.998393 1.200692 0.143792 0.078 Uiso 1 1 calc R U . . .
H7C H 0.999315 1.305596 0.086481 0.078 Uiso 1 1 calc R U . . .
C8 C 0.6886(7) 1.0433(8) -0.0885(3) 0.079(3) Uani 1 1 d . . . . .
H8A H 0.615421 1.002883 -0.096743 0.118 Uiso 1 1 calc R U . . .
H8B H 0.739411 0.969747 -0.094954 0.118 Uiso 1 1 calc R U . . .
H8C H 0.688918 1.123219 -0.117224 0.118 Uiso 1 1 calc R U . . .
C9 C 0.5938(5) 1.2025(6) 0.1126(3) 0.0485(17) Uani 1 1 d . . . . .
H9A H 0.629117 1.199974 0.157622 0.073 Uiso 1 1 calc R U . . .
H9B H 0.536828 1.129666 0.102703 0.073 Uiso 1 1 calc R U . . .
H9C H 0.561723 1.296967 0.101323 0.073 Uiso 1 1 calc R U . . .
C10 C 0.6857(4) 0.7320(5) 0.1496(2) 0.0210(10) Uani 1 1 d . . . . .
H10 H 0.612213 0.736377 0.119855 0.025 Uiso 1 1 calc R U . . .
C11 C 0.6864(4) 0.8455(6) 0.1998(2) 0.0302(12) Uani 1 1 d . . . . .
H11A H 0.757401 0.844007 0.231194 0.036 Uiso 1 1 calc R U . . .
H11B H 0.676889 0.941041 0.179979 0.036 Uiso 1 1 calc R U . . .
C12 C 0.5965(5) 0.8193(7) 0.2327(3) 0.0373(14) Uani 1 1 d . . . . .
H12A H 0.525346 0.82955 0.201986 0.045 Uiso 1 1 calc R U . . .
H12B H 0.600848 0.892207 0.265861 0.045 Uiso 1 1 calc R U . . .
C13 C 0.6045(5) 0.6714(7) 0.2621(3) 0.0423(16) Uani 1 1 d . . . . .
H13A H 0.671551 0.66477 0.296424 0.051 Uiso 1 1 calc R U . . .
H13B H 0.54186 0.655596 0.280339 0.051 Uiso 1 1 calc R U . . .
C14 C 0.6058(5) 0.5568(6) 0.2133(3) 0.0392(15) Uani 1 1 d . . . . .
H14A H 0.534725 0.555237 0.182035 0.047 Uiso 1 1 calc R U . . .
H14B H 0.617031 0.462351 0.234107 0.047 Uiso 1 1 calc R U . . .
C15 C 0.6953(4) 0.5833(5) 0.1797(2) 0.0275(12) Uani 1 1 d . . . . .
H15A H 0.690918 0.509986 0.146662 0.033 Uiso 1 1 calc R U . . .
H15B H 0.766879 0.574037 0.210109 0.033 Uiso 1 1 calc R U . . .
C16 C 0.7634(4) 0.6313(5) 0.0442(2) 0.0197(10) Uani 1 1 d . . . . .
H16 H 0.782111 0.538824 0.067016 0.024 Uiso 1 1 calc R U . . .
C17 C 0.6448(4) 0.6254(5) 0.0064(2) 0.0253(11) Uani 1 1 d . . . . .
H17A H 0.624141 0.71866 -0.014394 0.03 Uiso 1 1 calc R U . . .
H17B H 0.597864 0.608006 0.035317 0.03 Uiso 1 1 calc R U . . .
C18 C 0.6263(4) 0.5074(6) -0.0434(2) 0.0288(11) Uani 1 1 d . . . . .
H18A H 0.639582 0.413231 -0.022401 0.035 Uiso 1 1 calc R U . . .
H18B H 0.549865 0.509911 -0.068291 0.035 Uiso 1 1 calc R U . . .
C19 C 0.6999(5) 0.5246(6) -0.0867(2) 0.0369(14) Uani 1 1 d . . . . .
H19A H 0.680919 0.613488 -0.111441 0.044 Uiso 1 1 calc R U . . .
H19B H 0.689371 0.443413 -0.116463 0.044 Uiso 1 1 calc R U . . .
C20 C 0.8190(4) 0.5309(6) -0.0498(3) 0.0374(15) Uani 1 1 d . . . . .
H20A H 0.840241 0.438407 -0.028459 0.045 Uiso 1 1 calc R U . . .
H20B H 0.865388 0.547794 -0.079057 0.045 Uiso 1 1 calc R U . . .
C21 C 0.8363(4) 0.6501(6) -0.0011(2) 0.0287(12) Uani 1 1 d . . . . .
H21A H 0.820491 0.743238 -0.02283 0.034 Uiso 1 1 calc R U . . .
H21B H 0.913213 0.650735 0.023046 0.034 Uiso 1 1 calc R U . . .
C22 C 0.9182(4) 0.7343(5) 0.1589(2) 0.0215(10) Uani 1 1 d . . . . .
H22 H 0.908237 0.752604 0.201899 0.026 Uiso 1 1 calc R U . . .
C23 C 0.9590(4) 0.5805(5) 0.1596(2) 0.0268(11) Uani 1 1 d . . . . .
H23A H 0.972183 0.557422 0.118236 0.032 Uiso 1 1 calc R U . . .
H23B H 0.902769 0.514482 0.166934 0.032 Uiso 1 1 calc R U . . .
C24 C 1.0640(4) 0.5590(6) 0.2110(3) 0.0387(14) Uani 1 1 d . . . . .
H24A H 1.04883 0.571466 0.25268 0.046 Uiso 1 1 calc R U . . .
H24B H 1.090624 0.460429 0.208572 0.046 Uiso 1 1 calc R U . . .
C25 C 1.1512(4) 0.6644(6) 0.2043(3) 0.0407(15) Uani 1 1 d . . . . .
H25A H 1.215597 0.652715 0.240082 0.049 Uiso 1 1 calc R U . . .
H25B H 1.173482 0.643309 0.165183 0.049 Uiso 1 1 calc R U . . .
C26 C 1.1114(4) 0.8172(6) 0.2023(3) 0.0360(14) Uani 1 1 d . . . . .
H26A H 1.168096 0.882094 0.194669 0.043 Uiso 1 1 calc R U . . .
H26B H 1.098191 0.842296 0.243514 0.043 Uiso 1 1 calc R U . . .
C27 C 1.0068(4) 0.8379(6) 0.1507(3) 0.0303(12) Uani 1 1 d . . . . .
H27A H 1.021764 0.822066 0.109153 0.036 Uiso 1 1 calc R U . . .
H27B H 0.980952 0.937289 0.151951 0.036 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 P1 2.1025(13) . ?
NI1 C4 2.118(6) . ?
NI1 C5 2.124(5) . ?
NI1 C2 2.129(6) . ?
NI1 C6 2.131(5) . ?
NI1 C3 2.133(6) . ?
NI1 C1 2.150(5) . ?
P1 C16 1.860(5) . ?
P1 C10 1.870(5) . ?
P1 C22 1.880(5) . ?
C1 C2 1.405(8) . ?
C1 C6 1.416(8) . ?
C1 C7 1.495(8) . ?
C2 C3 1.405(9) . ?
C2 H2 0.95 . ?
C3 C4 1.409(9) . ?
C3 C8 1.521(8) . ?
C4 C5 1.420(8) . ?
C4 H4 0.95 . ?
C5 C6 1.411(8) . ?
C5 C9 1.504(8) . ?
C6 H6 0.95 . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 C11 1.530(7) . ?
C10 C15 1.533(7) . ?
C10 H10 1 . ?
C11 C12 1.520(7) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 C13 1.521(8) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 C14 1.520(8) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 C15 1.527(6) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 C17 1.531(6) . ?
C16 C21 1.533(6) . ?
C16 H16 1 . ?
C17 C18 1.533(7) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 C19 1.504(7) . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
C19 C20 1.531(7) . ?
C19 H19A 0.99 . ?
C19 H19B 0.99 . ?
C20 C21 1.524(7) . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
C22 C23 1.530(6) . ?
C22 C27 1.533(6) . ?
C22 H22 1 . ?
C23 C24 1.531(7) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C24 C25 1.521(8) . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
C25 C26 1.515(8) . ?
C25 H25A 0.99 . ?
C25 H25B 0.99 . ?
C26 C27 1.531(7) . ?
C26 H26A 0.99 . ?
C26 H26B 0.99 . ?
C27 H27A 0.99 . ?
C27 H27B 0.99 . ?

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
P1 NI1 C4 138.74(17) . . ?
P1 NI1 C5 137.22(17) . . ?
C4 NI1 C5 39.1(2) . . ?
P1 NI1 C2 139.77(18) . . ?
C4 NI1 C2 69.7(3) . . ?
C5 NI1 C2 83.0(2) . . ?
P1 NI1 C6 137.72(15) . . ?
C4 NI1 C6 69.9(2) . . ?
C5 NI1 C6 38.7(2) . . ?
C2 NI1 C6 69.3(2) . . ?
P1 NI1 C3 139.65(17) . . ?
C4 NI1 C3 38.7(2) . . ?
C5 NI1 C3 70.5(2) . . ?
C2 NI1 C3 38.5(2) . . ?
C6 NI1 C3 82.6(2) . . ?
P1 NI1 C1 138.15(18) . . ?
C4 NI1 C1 83.1(2) . . ?
C5 NI1 C1 70.4(2) . . ?
C2 NI1 C1 38.3(2) . . ?
C6 NI1 C1 38.6(2) . . ?
C3 NI1 C1 69.9(2) . . ?
C16 P1 C10 102.0(2) . . ?
C16 P1 C22 104.0(2) . . ?
C10 P1 C22 102.1(2) . . ?
C16 P1 NI1 116.68(16) . . ?
C10 P1 NI1 113.82(16) . . ?
C22 P1 NI1 116.26(16) . . ?
C2 C1 C6 118.3(6) . . ?
C2 C1 C7 121.0(6) . . ?
C6 C1 C7 120.7(6) . . ?
C2 C1 NI1 70.0(3) . . ?
C6 C1 NI1 69.9(3) . . ?
C7 C1 NI1 134.2(4) . . ?
C3 C2 C1 121.7(6) . . ?
C3 C2 NI1 70.9(3) . . ?
C1 C2 NI1 71.7(3) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
NI1 C2 H2 131.2 . . ?
C2 C3 C4 119.3(6) . . ?
C2 C3 C8 120.2(7) . . ?
C4 C3 C8 120.5(7) . . ?
C2 C3 NI1 70.6(3) . . ?
C4 C3 NI1 70.1(3) . . ?
C8 C3 NI1 132.5(4) . . ?
C3 C4 C5 120.6(6) . . ?
C3 C4 NI1 71.2(4) . . ?
C5 C4 NI1 70.7(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
NI1 C4 H4 131.2 . . ?
C6 C5 C4 118.7(6) . . ?
C6 C5 C9 120.2(6) . . ?
C4 C5 C9 121.1(6) . . ?
C6 C5 NI1 70.9(3) . . ?
C4 C5 NI1 70.2(3) . . ?
C9 C5 NI1 132.2(4) . . ?
C5 C6 C1 121.4(5) . . ?
C5 C6 NI1 70.4(3) . . ?
C1 C6 NI1 71.4(3) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
NI1 C6 H6 131.9 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 109.6(4) . . ?
C11 C10 P1 110.7(3) . . ?
C15 C10 P1 117.2(3) . . ?
C11 C10 H10 106.2 . . ?
C15 C10 H10 106.2 . . ?
P1 C10 H10 106.2 . . ?
C12 C11 C10 111.3(4) . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108 . . ?
C11 C12 C13 111.8(5) . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 110.8(4) . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 C15 111.7(5) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 C10 111.5(4) . . ?
C14 C15 H15A 109.3 . . ?
C10 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C10 C15 H15B 109.3 . . ?
H15A C15 H15B 108 . . ?
C17 C16 C21 109.2(4) . . ?
C17 C16 P1 110.8(3) . . ?
C21 C16 P1 111.0(3) . . ?
C17 C16 H16 108.6 . . ?
C21 C16 H16 108.6 . . ?
P1 C16 H16 108.6 . . ?
C16 C17 C18 111.6(4) . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108 . . ?
C19 C18 C17 111.5(4) . . ?
C19 C18 H18A 109.3 . . ?
C17 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C17 C18 H18B 109.3 . . ?
H18A C18 H18B 108 . . ?
C18 C19 C20 111.1(4) . . ?
C18 C19 H19A 109.4 . . ?
C20 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
C20 C19 H19B 109.4 . . ?
H19A C19 H19B 108 . . ?
C21 C20 C19 110.5(5) . . ?
C21 C20 H20A 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C20 C21 C16 111.5(4) . . ?
C20 C21 H21A 109.3 . . ?
C16 C21 H21A 109.3 . . ?
C20 C21 H21B 109.3 . . ?
C16 C21 H21B 109.3 . . ?
H21A C21 H21B 108 . . ?
C23 C22 C27 109.8(4) . . ?
C23 C22 P1 117.7(3) . . ?
C27 C22 P1 110.7(3) . . ?
C23 C22 H22 105.9 . . ?
C27 C22 H22 105.9 . . ?
P1 C22 H22 105.9 . . ?
C22 C23 C24 111.3(4) . . ?
C22 C23 H23A 109.4 . . ?
C24 C23 H23A 109.4 . . ?
C22 C23 H23B 109.4 . . ?
C24 C23 H23B 109.4 . . ?
H23A C23 H23B 108 . . ?
C25 C24 C23 111.5(5) . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24A 109.3 . . ?
C25 C24 H24B 109.3 . . ?
C23 C24 H24B 109.3 . . ?
H24A C24 H24B 108 . . ?
C26 C25 C24 111.6(4) . . ?
C26 C25 H25A 109.3 . . ?
C24 C25 H25A 109.3 . . ?
C26 C25 H25B 109.3 . . ?
C24 C25 H25B 109.3 . . ?
H25A C25 H25B 108 . . ?
C25 C26 C27 111.3(4) . . ?
C25 C26 H26A 109.4 . . ?
C27 C26 H26A 109.4 . . ?
C25 C26 H26B 109.4 . . ?
C27 C26 H26B 109.4 . . ?
H26A C26 H26B 108 . . ?
C26 C27 C22 111.2(4) . . ?
C26 C27 H27A 109.4 . . ?
C22 C27 H27A 109.4 . . ?
C26 C27 H27B 109.4 . . ?
C22 C27 H27B 109.4 . . ?
H27A C27 H27B 108 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1580330'
_audit_update_record             
;
2017-10-16 deposited with the CCDC.
2017-11-21 downloaded from the CCDC.
;

_audit_creation_date             2016-08-03T15:14:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C25  H41 Ni O P'
_chemical_formula_sum            'C25 H41 Ni O P'
_chemical_formula_weight         447.26
_chemical_compound_source        synthesized

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6352(5)
_cell_length_b                   9.7092(6)
_cell_length_c                   15.6942(10)
_cell_angle_alpha                97.5800(10)
_cell_angle_beta                 99.4610(10)
_cell_angle_gamma                115.0380(10)
_cell_volume                     1145.68(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    135(2)
_cell_measurement_reflns_used    55092
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      32.64
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             484

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   twinabs
_exptl_absorpt_correction_T_min  0.765321
_exptl_absorpt_correction_T_max  0.862329

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      135(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_number            32139
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.923
_diffrn_reflns_theta_max         32.636
_diffrn_reflns_theta_full        32.5
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             32139
_reflns_number_gt                25298
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   iterative
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refined as a 3-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+1.5095P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         32139
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0638
_refine_ls_wR_factor_ref         0.1095
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.153
_refine_diff_density_min         -0.781
_refine_diff_density_rms         0.145

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.22460(4) 0.43077(3) 0.35600(2) 0.01251(7) Uani 1 1 d . . . . .
P1 P 0.30220(7) 0.34455(6) 0.24968(4) 0.01076(11) Uani 1 1 d . . . . .
O1 O -0.1399(2) 0.1901(2) 0.39557(13) 0.0237(4) Uani 1 1 d . . . . .
C1 C 0.0049(3) 0.3335(3) 0.41534(16) 0.0167(4) Uani 1 1 d . . . . .
C2 C 0.1637(3) 0.3758(3) 0.47761(15) 0.0166(4) Uani 1 1 d . . . . .
H2 H 0.177105 0.302303 0.508614 0.02 Uiso 1 1 calc R U . . .
C3 C 0.3030(3) 0.5284(3) 0.49372(15) 0.0180(4) Uani 1 1 d . . . . .
H3 H 0.410377 0.5573 0.535701 0.022 Uiso 1 1 calc R U . . .
C4 C 0.2838(3) 0.6377(3) 0.44805(16) 0.0190(5) Uani 1 1 d . . . . .
H4 H 0.376514 0.740975 0.460153 0.023 Uiso 1 1 calc R U . . .
C5 C 0.1261(3) 0.5928(3) 0.38426(17) 0.0194(5) Uani 1 1 d . . . . .
H5 H 0.113356 0.665511 0.35239 0.023 Uiso 1 1 calc R U . . .
C6 C -0.0128(3) 0.4407(3) 0.36736(16) 0.0187(5) Uani 1 1 d . . . . .
H6 H -0.118309 0.410568 0.323625 0.022 Uiso 1 1 calc R U . . .
C7 C -0.1235(4) 0.0763(3) 0.4392(2) 0.0293(6) Uani 1 1 d . . . . .
H7A H -0.025808 0.058499 0.425454 0.044 Uiso 1 1 calc R U . . .
H7B H -0.233194 -0.02149 0.418807 0.044 Uiso 1 1 calc R U . . .
H7C H -0.099989 0.113226 0.503341 0.044 Uiso 1 1 calc R U . . .
C8 C 0.4804(3) 0.4948(2) 0.21145(14) 0.0123(4) Uani 1 1 d . . . . .
H8 H 0.430762 0.56363 0.189749 0.015 Uiso 1 1 calc R U . . .
C9 C 0.6393(3) 0.6004(3) 0.28940(15) 0.0153(4) Uani 1 1 d . . . . .
H9A H 0.598748 0.644339 0.336546 0.018 Uiso 1 1 calc R U . . .
H9B H 0.692315 0.537282 0.314282 0.018 Uiso 1 1 calc R U . . .
C10 C 0.7796(3) 0.7342(3) 0.26113(17) 0.0202(5) Uani 1 1 d . . . . .
H10A H 0.732077 0.806273 0.244683 0.024 Uiso 1 1 calc R U . . .
H10B H 0.88389 0.793454 0.311829 0.024 Uiso 1 1 calc R U . . .
C11 C 0.8361(3) 0.6751(3) 0.18282(18) 0.0227(5) Uani 1 1 d . . . . .
H11A H 0.919638 0.764976 0.163694 0.027 Uiso 1 1 calc R U . . .
H11B H 0.897376 0.613805 0.201344 0.027 Uiso 1 1 calc R U . . .
C12 C 0.6773(3) 0.5735(3) 0.10558(17) 0.0232(5) Uani 1 1 d . . . . .
H12A H 0.716145 0.532677 0.056499 0.028 Uiso 1 1 calc R U . . .
H12B H 0.621885 0.637051 0.083633 0.028 Uiso 1 1 calc R U . . .
C13 C 0.5421(3) 0.4369(3) 0.13452(16) 0.0182(5) Uani 1 1 d . . . . .
H13A H 0.439244 0.373013 0.083701 0.022 Uiso 1 1 calc R U . . .
H13B H 0.595596 0.369959 0.152983 0.022 Uiso 1 1 calc R U . . .
C14 C 0.1225(3) 0.2461(3) 0.14581(14) 0.0132(4) Uani 1 1 d . . . . .
H14 H 0.166307 0.200194 0.100282 0.016 Uiso 1 1 calc R U . . .
C15 C -0.0375(3) 0.1138(3) 0.16381(16) 0.0166(4) Uani 1 1 d . . . . .
H15A H -0.002555 0.036372 0.183917 0.02 Uiso 1 1 calc R U . . .
H15B H -0.076352 0.157107 0.21203 0.02 Uiso 1 1 calc R U . . .
C16 C -0.1914(3) 0.0323(3) 0.08120(17) 0.0205(5) Uani 1 1 d . . . . .
H16A H -0.15616 -0.018132 0.034276 0.025 Uiso 1 1 calc R U . . .
H16B H -0.292974 -0.049858 0.095824 0.025 Uiso 1 1 calc R U . . .
C17 C -0.2455(3) 0.1494(3) 0.04734(17) 0.0227(5) Uani 1 1 d . . . . .
H17A H -0.341771 0.095779 -0.007359 0.027 Uiso 1 1 calc R U . . .
H17B H -0.290221 0.193293 0.092388 0.027 Uiso 1 1 calc R U . . .
C18 C -0.0899(3) 0.2807(3) 0.02788(17) 0.0239(5) Uani 1 1 d . . . . .
H18A H -0.12646 0.358053 0.008981 0.029 Uiso 1 1 calc R U . . .
H18B H -0.053431 0.237846 -0.021542 0.029 Uiso 1 1 calc R U . . .
C19 C 0.0673(3) 0.3623(3) 0.10930(16) 0.0182(5) Uani 1 1 d . . . . .
H19A H 0.035369 0.416363 0.156171 0.022 Uiso 1 1 calc R U . . .
H19B H 0.168251 0.441854 0.092883 0.022 Uiso 1 1 calc R U . . .
C20 C 0.3857(3) 0.1977(2) 0.26677(14) 0.0122(4) Uani 1 1 d . . . . .
H20 H 0.515805 0.259644 0.292172 0.015 Uiso 1 1 calc R U . . .
C21 C 0.3127(3) 0.1119(3) 0.33782(15) 0.0150(4) Uani 1 1 d . . . . .
H21A H 0.332323 0.189323 0.391431 0.018 Uiso 1 1 calc R U . . .
H21B H 0.184023 0.045274 0.315261 0.018 Uiso 1 1 calc R U . . .
C22 C 0.4013(3) 0.0104(3) 0.36265(16) 0.0182(4) Uani 1 1 d . . . . .
H22A H 0.527933 0.078208 0.390986 0.022 Uiso 1 1 calc R U . . .
H22B H 0.347023 -0.046959 0.406125 0.022 Uiso 1 1 calc R U . . .
C23 C 0.3828(3) -0.1061(3) 0.28129(17) 0.0205(5) Uani 1 1 d . . . . .
H23A H 0.448207 -0.164727 0.2988 0.025 Uiso 1 1 calc R U . . .
H23B H 0.257036 -0.181776 0.256843 0.025 Uiso 1 1 calc R U . . .
C24 C 0.4545(3) -0.0220(3) 0.21055(16) 0.0187(5) Uani 1 1 d . . . . .
H24A H 0.436016 -0.099678 0.157302 0.022 Uiso 1 1 calc R U . . .
H24B H 0.582921 0.04603 0.233111 0.022 Uiso 1 1 calc R U . . .
C25 C 0.3627(3) 0.0771(3) 0.18509(15) 0.0152(4) Uani 1 1 d . . . . .
H25A H 0.235544 0.008168 0.158812 0.018 Uiso 1 1 calc R U . . .
H25B H 0.413156 0.131916 0.139937 0.018 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 P1 2.0996(6) . ?
NI1 C3 2.113(2) . ?
NI1 C5 2.113(2) . ?
NI1 C4 2.123(2) . ?
NI1 C6 2.128(2) . ?
NI1 C2 2.137(2) . ?
NI1 C1 2.157(2) . ?
P1 C14 1.866(2) . ?
P1 C8 1.868(2) . ?
P1 C20 1.880(2) . ?
O1 C1 1.373(3) . ?
O1 C7 1.418(3) . ?
C1 C6 1.406(3) . ?
C1 C2 1.407(3) . ?
C2 C3 1.414(3) . ?
C2 H2 0.95 . ?
C3 C4 1.406(3) . ?
C3 H3 0.95 . ?
C4 C5 1.407(3) . ?
C4 H4 0.95 . ?
C5 C6 1.408(3) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 C13 1.531(3) . ?
C8 C9 1.535(3) . ?
C8 H8 1 . ?
C9 C10 1.533(3) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.525(3) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C12 1.522(4) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 C13 1.533(3) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 C15 1.536(3) . ?
C14 C19 1.537(3) . ?
C14 H14 1 . ?
C15 C16 1.532(3) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 C17 1.523(4) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 C18 1.521(4) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 C19 1.535(3) . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
C19 H19A 0.99 . ?
C19 H19B 0.99 . ?
C20 C21 1.538(3) . ?
C20 C25 1.542(3) . ?
C20 H20 1 . ?
C21 C22 1.533(3) . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
C22 C23 1.528(3) . ?
C22 H22A 0.99 . ?
C22 H22B 0.99 . ?
C23 C24 1.523(3) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C24 C25 1.535(3) . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
C25 H25A 0.99 . ?
C25 H25B 0.99 . ?

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
P1 NI1 C3 143.82(7) . . ?
P1 NI1 C5 137.30(7) . . ?
C3 NI1 C5 70.19(9) . . ?
P1 NI1 C4 142.91(7) . . ?
C3 NI1 C4 38.79(9) . . ?
C5 NI1 C4 38.81(9) . . ?
P1 NI1 C6 133.00(7) . . ?
C3 NI1 C6 83.08(9) . . ?
C5 NI1 C6 38.78(9) . . ?
C4 NI1 C6 70.18(10) . . ?
P1 NI1 C2 139.03(7) . . ?
C3 NI1 C2 38.86(9) . . ?
C5 NI1 C2 82.97(9) . . ?
C4 NI1 C2 70.17(9) . . ?
C6 NI1 C2 69.76(9) . . ?
P1 NI1 C1 134.37(7) . . ?
C3 NI1 C1 69.61(9) . . ?
C5 NI1 C1 69.52(9) . . ?
C4 NI1 C1 82.46(9) . . ?
C6 NI1 C1 38.30(9) . . ?
C2 NI1 C1 38.26(9) . . ?
C14 P1 C8 102.03(10) . . ?
C14 P1 C20 104.02(10) . . ?
C8 P1 C20 103.33(10) . . ?
C14 P1 NI1 113.55(7) . . ?
C8 P1 NI1 115.44(7) . . ?
C20 P1 NI1 116.70(7) . . ?
C1 O1 C7 116.7(2) . . ?
O1 C1 C6 115.2(2) . . ?
O1 C1 C2 124.6(2) . . ?
C6 C1 C2 120.2(2) . . ?
O1 C1 NI1 132.69(17) . . ?
C6 C1 NI1 69.71(13) . . ?
C2 C1 NI1 70.09(13) . . ?
C1 C2 C3 119.5(2) . . ?
C1 C2 NI1 71.66(13) . . ?
C3 C2 NI1 69.65(13) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
NI1 C2 H2 131.1 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 NI1 71.00(14) . . ?
C2 C3 NI1 71.48(13) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
NI1 C3 H3 130.4 . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 NI1 70.22(13) . . ?
C5 C4 NI1 70.22(14) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
NI1 C4 H4 132.1 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 NI1 70.98(14) . . ?
C6 C5 NI1 71.17(13) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
NI1 C5 H5 130.8 . . ?
C1 C6 C5 119.8(2) . . ?
C1 C6 NI1 71.99(13) . . ?
C5 C6 NI1 70.05(13) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
NI1 C6 H6 130.5 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 110.09(18) . . ?
C13 C8 P1 117.19(15) . . ?
C9 C8 P1 111.05(15) . . ?
C13 C8 H8 105.9 . . ?
C9 C8 H8 105.9 . . ?
P1 C8 H8 105.9 . . ?
C10 C9 C8 111.92(19) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 111.9(2) . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C10 110.9(2) . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C13 110.5(2) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C8 C13 C12 111.30(19) . . ?
C8 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C8 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108 . . ?
C15 C14 C19 109.74(18) . . ?
C15 C14 P1 109.78(15) . . ?
C19 C14 P1 111.26(15) . . ?
C15 C14 H14 108.7 . . ?
C19 C14 H14 108.7 . . ?
P1 C14 H14 108.7 . . ?
C16 C15 C14 111.92(19) . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C15 110.5(2) . . ?
C17 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C18 C17 C16 110.7(2) . . ?
C18 C17 H17A 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 C19 111.7(2) . . ?
C17 C18 H18A 109.3 . . ?
C19 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
C19 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 C14 111.8(2) . . ?
C18 C19 H19A 109.3 . . ?
C14 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
C14 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
C21 C20 C25 109.11(17) . . ?
C21 C20 P1 111.08(15) . . ?
C25 C20 P1 118.46(15) . . ?
C21 C20 H20 105.8 . . ?
C25 C20 H20 105.8 . . ?
P1 C20 H20 105.8 . . ?
C22 C21 C20 111.57(18) . . ?
C22 C21 H21A 109.3 . . ?
C20 C21 H21A 109.3 . . ?
C22 C21 H21B 109.3 . . ?
C20 C21 H21B 109.3 . . ?
H21A C21 H21B 108 . . ?
C23 C22 C21 111.49(19) . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 108 . . ?
C24 C23 C22 110.61(19) . . ?
C24 C23 H23A 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 108.1 . . ?
C23 C24 C25 111.1(2) . . ?
C23 C24 H24A 109.4 . . ?
C25 C24 H24A 109.4 . . ?
C23 C24 H24B 109.4 . . ?
C25 C24 H24B 109.4 . . ?
H24A C24 H24B 108 . . ?
C24 C25 C20 110.99(18) . . ?
C24 C25 H25A 109.4 . . ?
C20 C25 H25A 109.4 . . ?
C24 C25 H25B 109.4 . . ?
C20 C25 H25B 109.4 . . ?
H25A C25 H25B 108 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1580331'
_audit_update_record             
;
2017-10-16 deposited with the CCDC.
2017-11-21 downloaded from the CCDC.
;

_audit_creation_date             2017-05-21T23:12:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C26  H37  F6 Ni P'
_chemical_formula_sum            'C26 H37 F6 Ni P'
_chemical_formula_weight         553.23
_chemical_compound_source        synthesized

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.921(4)
_cell_length_b                   9.399(2)
_cell_length_c                   32.999(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.990(4)
_cell_angle_gamma                90
_cell_volume                     5169(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    8896
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      25.94
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2320

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction'
_exptl_absorpt_correction_T_min  0.8093
_exptl_absorpt_correction_T_max  0.8622

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_number            47466
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         30
_diffrn_reflns_theta_full        30
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             7542
_reflns_number_gt                5118
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   iterative
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0310P)²+4.9895P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7542
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.0866
_refine_ls_wR_factor_gt          0.076
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.074

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.38730(2) 0.48758(2) 0.13498(2) 0.01831(7) Uani 1 1 d . . . . .
P1 P 0.36866(3) 0.71260(5) 0.13465(2) 0.01601(11) Uani 1 1 d . . . . .
F1 F 0.59652(10) 0.23308(19) 0.18922(7) 0.0872(7) Uani 1 1 d . . . . .
F2 F 0.56345(10) 0.4228(2) 0.21712(4) 0.0686(5) Uani 1 1 d . . . . .
F3 F 0.60762(8) 0.43347(18) 0.16095(4) 0.0505(4) Uani 1 1 d . . . . .
F4 F 0.42312(9) 0.37754(15) 0.03075(4) 0.0463(4) Uani 1 1 d . . . . .
F5 F 0.29745(9) 0.35670(17) 0.03084(4) 0.0533(4) Uani 1 1 d . . . . .
F6 F 0.37170(10) 0.17165(14) 0.03477(4) 0.0509(4) Uani 1 1 d . . . . .
C1 C 0.47702(12) 0.3417(2) 0.15836(6) 0.0232(4) Uani 1 1 d . . . . .
C2 C 0.46302(12) 0.3354(2) 0.11491(6) 0.0227(4) Uani 1 1 d . . . . .
H2 H 0.506382 0.344384 0.10025 0.027 Uiso 1 1 calc R U . . .
C3 C 0.38424(12) 0.31581(19) 0.09356(6) 0.0221(4) Uani 1 1 d . . . . .
C4 C 0.32018(13) 0.3009(2) 0.11543(7) 0.0252(4) Uani 1 1 d . . . . .
H4 H 0.267022 0.287847 0.100985 0.03 Uiso 1 1 calc R U . . .
C5 C 0.33505(13) 0.3053(2) 0.15849(7) 0.0281(5) Uani 1 1 d . . . . .
H5 H 0.291803 0.294146 0.173127 0.034 Uiso 1 1 calc R U . . .
C6 C 0.41253(13) 0.3260(2) 0.18013(6) 0.0267(5) Uani 1 1 d . . . . .
H6 H 0.421991 0.329539 0.209345 0.032 Uiso 1 1 calc R U . . .
C7 C 0.56024(14) 0.3583(3) 0.18100(7) 0.0350(5) Uani 1 1 d . . . . .
C8 C 0.36894(14) 0.3066(2) 0.04768(7) 0.0307(5) Uani 1 1 d . . . . .
C9 C 0.26955(11) 0.77546(19) 0.10627(6) 0.0198(4) Uani 1 1 d . . . . .
H9 H 0.233097 0.779747 0.127068 0.024 Uiso 1 1 calc R U . . .
C10 C 0.26745(12) 0.9246(2) 0.08694(6) 0.0228(4) Uani 1 1 d . . . . .
H10A H 0.287892 0.99502 0.108548 0.027 Uiso 1 1 calc R U . . .
H10B H 0.30318 0.926494 0.066155 0.027 Uiso 1 1 calc R U . . .
C11 C 0.18283(13) 0.9662(2) 0.06659(6) 0.0281(5) Uani 1 1 d . . . . .
H11A H 0.148505 0.974833 0.087899 0.034 Uiso 1 1 calc R U . . .
H11B H 0.184365 1.060194 0.053198 0.034 Uiso 1 1 calc R U . . .
C12 C 0.14669(13) 0.8580(2) 0.03488(7) 0.0318(5) Uani 1 1 d . . . . .
H12A H 0.177229 0.857736 0.011861 0.038 Uiso 1 1 calc R U . . .
H12B H 0.090628 0.885269 0.023688 0.038 Uiso 1 1 calc R U . . .
C13 C 0.14780(12) 0.7095(2) 0.05322(7) 0.0308(5) Uani 1 1 d . . . . .
H13A H 0.127934 0.640366 0.031174 0.037 Uiso 1 1 calc R U . . .
H13B H 0.11131 0.706511 0.073631 0.037 Uiso 1 1 calc R U . . .
C14 C 0.23233(12) 0.6671(2) 0.07408(6) 0.0244(4) Uani 1 1 d . . . . .
H14A H 0.230063 0.573201 0.087453 0.029 Uiso 1 1 calc R U . . .
H14B H 0.266947 0.657497 0.052933 0.029 Uiso 1 1 calc R U . . .
C15 C 0.44350(11) 0.82005(19) 0.11282(6) 0.0179(4) Uani 1 1 d . . . . .
H15 H 0.424925 0.921211 0.110819 0.021 Uiso 1 1 calc R U . . .
C16 C 0.44785(12) 0.7667(2) 0.06931(6) 0.0256(5) Uani 1 1 d . . . . .
H16A H 0.463063 0.664907 0.070588 0.031 Uiso 1 1 calc R U . . .
H16B H 0.394231 0.775236 0.051852 0.031 Uiso 1 1 calc R U . . .
C17 C 0.50875(12) 0.8511(2) 0.04984(6) 0.0275(5) Uani 1 1 d . . . . .
H17A H 0.511455 0.811713 0.022291 0.033 Uiso 1 1 calc R U . . .
H17B H 0.491286 0.951535 0.046364 0.033 Uiso 1 1 calc R U . . .
C18 C 0.59093(12) 0.8442(2) 0.07652(7) 0.0292(5) Uani 1 1 d . . . . .
H18A H 0.628932 0.903173 0.064107 0.035 Uiso 1 1 calc R U . . .
H18B H 0.610525 0.744766 0.077806 0.035 Uiso 1 1 calc R U . . .
C19 C 0.58828(13) 0.8970(3) 0.11975(7) 0.0316(5) Uani 1 1 d . . . . .
H19A H 0.574492 0.999481 0.118684 0.038 Uiso 1 1 calc R U . . .
H19B H 0.642052 0.886206 0.136915 0.038 Uiso 1 1 calc R U . . .
C20 C 0.52655(12) 0.8151(2) 0.13968(6) 0.0276(5) Uani 1 1 d . . . . .
H20A H 0.543888 0.714809 0.143945 0.033 Uiso 1 1 calc R U . . .
H20B H 0.523819 0.857013 0.166922 0.033 Uiso 1 1 calc R U . . .
C21 C 0.37339(12) 0.7852(2) 0.18754(6) 0.0206(4) Uani 1 1 d . . . . .
H21 H 0.429685 0.769454 0.202052 0.025 Uiso 1 1 calc R U . . .
C22 C 0.35722(13) 0.9442(2) 0.19095(6) 0.0255(5) Uani 1 1 d . . . . .
H22A H 0.301943 0.965708 0.176898 0.031 Uiso 1 1 calc R U . . .
H22B H 0.394893 0.998484 0.177007 0.031 Uiso 1 1 calc R U . . .
C23 C 0.36721(14) 0.9909(2) 0.23609(6) 0.0308(5) Uani 1 1 d . . . . .
H23A H 0.423875 0.978216 0.249401 0.037 Uiso 1 1 calc R U . . .
H23B H 0.353841 1.093147 0.237368 0.037 Uiso 1 1 calc R U . . .
C24 C 0.31371(14) 0.9057(2) 0.25921(6) 0.0312(5) Uani 1 1 d . . . . .
H24A H 0.256818 0.92554 0.247589 0.037 Uiso 1 1 calc R U . . .
H24B H 0.323332 0.935171 0.288455 0.037 Uiso 1 1 calc R U . . .
C25 C 0.32976(14) 0.7473(2) 0.25639(6) 0.0303(5) Uani 1 1 d . . . . .
H25A H 0.292174 0.693836 0.270588 0.036 Uiso 1 1 calc R U . . .
H25B H 0.38508 0.726205 0.270438 0.036 Uiso 1 1 calc R U . . .
C26 C 0.31950(13) 0.6986(2) 0.21139(6) 0.0249(4) Uani 1 1 d . . . . .
H26A H 0.262725 0.710123 0.198149 0.03 Uiso 1 1 calc R U . . .
H26B H 0.333361 0.596433 0.210442 0.03 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C1 2.0911(19) . ?
NI1 C2 2.1022(19) . ?
NI1 C3 2.1102(19) . ?
NI1 C6 2.118(2) . ?
NI1 C4 2.129(2) . ?
NI1 C5 2.134(2) . ?
NI1 P1 2.1381(7) . ?
P1 C15 1.8600(18) . ?
P1 C21 1.8626(19) . ?
P1 C9 1.869(2) . ?
F1 C7 1.333(3) . ?
F2 C7 1.330(3) . ?
F3 C7 1.328(3) . ?
F4 C8 1.333(3) . ?
F5 C8 1.327(3) . ?
F6 C8 1.341(2) . ?
C1 C2 1.413(3) . ?
C1 C6 1.414(3) . ?
C1 C7 1.483(3) . ?
C2 C3 1.408(3) . ?
C2 H2 0.95 . ?
C3 C4 1.410(3) . ?
C3 C8 1.493(3) . ?
C4 C5 1.400(3) . ?
C4 H4 0.95 . ?
C5 C6 1.393(3) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C9 C14 1.527(3) . ?
C9 C10 1.538(3) . ?
C9 H9 1 . ?
C10 C11 1.523(3) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C12 1.510(3) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 C13 1.520(3) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 C14 1.529(3) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C15 C20 1.527(3) . ?
C15 C16 1.534(3) . ?
C15 H15 1 . ?
C16 C17 1.527(3) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 C18 1.513(3) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 C19 1.519(3) . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
C19 C20 1.534(3) . ?
C19 H19A 0.99 . ?
C19 H19B 0.99 . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?
C21 C22 1.527(3) . ?
C21 C26 1.537(3) . ?
C21 H21 1 . ?
C22 C23 1.534(3) . ?
C22 H22A 0.99 . ?
C22 H22B 0.99 . ?
C23 C24 1.510(3) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C24 C25 1.519(3) . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
C25 C26 1.535(3) . ?
C25 H25A 0.99 . ?
C25 H25B 0.99 . ?
C26 H26A 0.99 . ?
C26 H26B 0.99 . ?

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
C1 NI1 C2 39.39(7) . . ?
C1 NI1 C3 70.86(8) . . ?
C2 NI1 C3 39.04(8) . . ?
C1 NI1 C6 39.26(8) . . ?
C2 NI1 C6 71.00(8) . . ?
C3 NI1 C6 83.48(8) . . ?
C1 NI1 C4 83.48(8) . . ?
C2 NI1 C4 70.50(8) . . ?
C3 NI1 C4 38.85(7) . . ?
C6 NI1 C4 69.76(8) . . ?
C1 NI1 C5 70.11(8) . . ?
C2 NI1 C5 83.23(8) . . ?
C3 NI1 C5 69.90(8) . . ?
C6 NI1 C5 38.25(8) . . ?
C4 NI1 C5 38.34(8) . . ?
C1 NI1 P1 138.36(6) . . ?
C2 NI1 P1 140.24(6) . . ?
C3 NI1 P1 140.05(5) . . ?
C6 NI1 P1 136.40(6) . . ?
C4 NI1 P1 138.02(6) . . ?
C5 NI1 P1 136.52(6) . . ?
C15 P1 C21 104.05(8) . . ?
C15 P1 C9 104.25(9) . . ?
C21 P1 C9 104.05(9) . . ?
C15 P1 NI1 115.42(6) . . ?
C21 P1 NI1 112.03(6) . . ?
C9 P1 NI1 115.72(6) . . ?
C2 C1 C6 120.18(19) . . ?
C2 C1 C7 119.52(18) . . ?
C6 C1 C7 120.24(18) . . ?
C2 C1 NI1 70.73(11) . . ?
C6 C1 NI1 71.41(11) . . ?
C7 C1 NI1 133.00(15) . . ?
C3 C2 C1 119.39(18) . . ?
C3 C2 NI1 70.78(11) . . ?
C1 C2 NI1 69.88(11) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
NI1 C2 H2 131.8 . . ?
C2 C3 C4 120.15(18) . . ?
C2 C3 C8 119.84(18) . . ?
C4 C3 C8 119.98(19) . . ?
C2 C3 NI1 70.17(11) . . ?
C4 C3 NI1 71.28(11) . . ?
C8 C3 NI1 132.97(14) . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 NI1 71.05(12) . . ?
C3 C4 NI1 69.87(11) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
NI1 C4 H4 131.9 . . ?
C6 C5 C4 120.79(19) . . ?
C6 C5 NI1 70.26(11) . . ?
C4 C5 NI1 70.60(11) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
NI1 C5 H5 132.7 . . ?
C5 C6 C1 119.62(19) . . ?
C5 C6 NI1 71.49(12) . . ?
C1 C6 NI1 69.33(11) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
NI1 C6 H6 131.8 . . ?
F3 C7 F2 105.6(2) . . ?
F3 C7 F1 105.9(2) . . ?
F2 C7 F1 105.9(2) . . ?
F3 C7 C1 114.03(18) . . ?
F2 C7 C1 112.76(19) . . ?
F1 C7 C1 111.9(2) . . ?
F5 C8 F4 106.85(18) . . ?
F5 C8 F6 106.39(18) . . ?
F4 C8 F6 106.00(18) . . ?
F5 C8 C3 112.90(18) . . ?
F4 C8 C3 112.64(18) . . ?
F6 C8 C3 111.58(18) . . ?
C14 C9 C10 110.05(16) . . ?
C14 C9 P1 111.32(13) . . ?
C10 C9 P1 116.75(14) . . ?
C14 C9 H9 106 . . ?
C10 C9 H9 106 . . ?
P1 C9 H9 106 . . ?
C11 C10 C9 111.65(17) . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108 . . ?
C12 C11 C10 111.68(17) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 111.51(18) . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108 . . ?
C12 C13 C14 111.42(17) . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108 . . ?
C9 C14 C13 112.31(17) . . ?
C9 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
C9 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
C20 C15 C16 110.16(16) . . ?
C20 C15 P1 112.24(13) . . ?
C16 C15 P1 109.36(13) . . ?
C20 C15 H15 108.3 . . ?
C16 C15 H15 108.3 . . ?
P1 C15 H15 108.3 . . ?
C17 C16 C15 111.67(16) . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C18 C17 C16 110.62(17) . . ?
C18 C17 H17A 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 C19 111.02(17) . . ?
C17 C18 H18A 109.4 . . ?
C19 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
C19 C18 H18B 109.4 . . ?
H18A C18 H18B 108 . . ?
C18 C19 C20 111.81(18) . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
C15 C20 C19 111.25(17) . . ?
C15 C20 H20A 109.4 . . ?
C19 C20 H20A 109.4 . . ?
C15 C20 H20B 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108 . . ?
C22 C21 C26 110.54(16) . . ?
C22 C21 P1 116.62(13) . . ?
C26 C21 P1 110.67(13) . . ?
C22 C21 H21 106.1 . . ?
C26 C21 H21 106.1 . . ?
P1 C21 H21 106.1 . . ?
C21 C22 C23 111.13(16) . . ?
C21 C22 H22A 109.4 . . ?
C23 C22 H22A 109.4 . . ?
C21 C22 H22B 109.4 . . ?
C23 C22 H22B 109.4 . . ?
H22A C22 H22B 108 . . ?
C24 C23 C22 111.35(17) . . ?
C24 C23 H23A 109.4 . . ?
C22 C23 H23A 109.4 . . ?
C24 C23 H23B 109.4 . . ?
C22 C23 H23B 109.4 . . ?
H23A C23 H23B 108 . . ?
C23 C24 C25 111.05(17) . . ?
C23 C24 H24A 109.4 . . ?
C25 C24 H24A 109.4 . . ?
C23 C24 H24B 109.4 . . ?
C25 C24 H24B 109.4 . . ?
H24A C24 H24B 108 . . ?
C24 C25 C26 111.13(17) . . ?
C24 C25 H25A 109.4 . . ?
C26 C25 H25A 109.4 . . ?
C24 C25 H25B 109.4 . . ?
C26 C25 H25B 109.4 . . ?
H25A C25 H25B 108 . . ?
C25 C26 C21 111.09(17) . . ?
C25 C26 H26A 109.4 . . ?
C21 C26 H26A 109.4 . . ?
C25 C26 H26B 109.4 . . ?
C21 C26 H26B 109.4 . . ?
H26A C26 H26B 108 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1580334'
_audit_update_record             
;
2017-10-16 deposited with the CCDC.
2017-11-21 downloaded from the CCDC.
;

_audit_creation_date             2016-05-16T13:41:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C25  H41  Ni P'
_chemical_formula_sum            'C25 H41 Ni P'
_chemical_formula_weight         431.26
_chemical_compound_source        synthesized

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6764(6)
_cell_length_b                   9.5709(7)
_cell_length_c                   15.6496(11)
_cell_angle_alpha                96.519(2)
_cell_angle_beta                 99.003(2)
_cell_angle_gamma                115.531(2)
_cell_volume                     1134.08(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    105(2)
_cell_measurement_reflns_used    9826
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      35.63
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             468

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS-2014/5'
_exptl_absorpt_correction_T_min  0.764
_exptl_absorpt_correction_T_max  0.802

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      105(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_number            56664
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.922
_diffrn_reflns_theta_max         34.999
_diffrn_reflns_theta_full        34.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             9957
_reflns_number_gt                7992
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   iterative
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0258P)²+0.5408P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         9957
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0719
_refine_ls_wR_factor_gt          0.0655
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.49
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.079

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.28725(2) 0.58762(2) 0.14254(2) 0.01033(4) Uani 1 1 d . . . . .
P1 P 0.21031(3) 0.66657(3) 0.25117(2) 0.00845(5) Uani 1 1 d . . . . .
C1 C 0.47978(15) 0.70688(14) 0.07131(7) 0.01481(19) Uani 1 1 d . . . . .
C2 C 0.31120(15) 0.63962(13) 0.01518(7) 0.01387(19) Uani 1 1 d . . . . .
H2 H 0.2766 0.704 -0.0169 0.017 Uiso 1 1 calc R U . . .
C3 C 0.19281(15) 0.47873(14) 0.00564(7) 0.0154(2) Uani 1 1 d . . . . .
H3 H 0.0797 0.4353 -0.0326 0.018 Uiso 1 1 calc R U . . .
C4 C 0.24270(17) 0.38251(14) 0.05293(8) 0.0181(2) Uani 1 1 d . . . . .
H4 H 0.1631 0.2742 0.0472 0.022 Uiso 1 1 calc R U . . .
C5 C 0.41149(17) 0.44774(15) 0.10892(8) 0.0191(2) Uani 1 1 d . . . . .
H5 H 0.4461 0.3831 0.1407 0.023 Uiso 1 1 calc R U . . .
C6 C 0.52877(15) 0.60851(15) 0.11781(8) 0.0178(2) Uani 1 1 d . . . . .
H6 H 0.6424 0.6516 0.1555 0.021 Uiso 1 1 calc R U . . .
C7 C 0.60405(17) 0.87887(15) 0.07987(9) 0.0233(2) Uani 1 1 d . . . . .
H7A H 0.6713 0.8905 0.0341 0.035 Uiso 1 1 calc R U . . .
H7B H 0.6846 0.9193 0.1383 0.035 Uiso 1 1 calc R U . . .
H7C H 0.5371 0.9388 0.0729 0.035 Uiso 1 1 calc R U . . .
C8 C 0.02951(13) 0.51416(12) 0.28997(7) 0.01007(17) Uani 1 1 d . . . . .
H8 H 0.0754 0.4417 0.3113 0.012 Uiso 1 1 calc R U . . .
C9 C -0.12771(14) 0.41241(13) 0.21228(7) 0.01303(18) Uani 1 1 d . . . . .
H9A H -0.177 0.4795 0.188 0.016 Uiso 1 1 calc R U . . .
H9B H -0.0876 0.3687 0.1649 0.016 Uiso 1 1 calc R U . . .
C10 C -0.27094(15) 0.27637(13) 0.24048(8) 0.0168(2) Uani 1 1 d . . . . .
H10A H -0.3734 0.2183 0.1899 0.02 Uiso 1 1 calc R U . . .
H10B H -0.2263 0.2018 0.2576 0.02 Uiso 1 1 calc R U . . .
C11 C -0.32847(16) 0.33630(14) 0.31799(8) 0.0195(2) Uani 1 1 d . . . . .
H11A H -0.4155 0.2452 0.337 0.023 Uiso 1 1 calc R U . . .
H11B H -0.3852 0.4015 0.2991 0.023 Uiso 1 1 calc R U . . .
C12 C -0.17156(16) 0.43488(14) 0.39542(8) 0.0188(2) Uani 1 1 d . . . . .
H12A H -0.1209 0.3674 0.4177 0.023 Uiso 1 1 calc R U . . .
H12B H -0.2107 0.4763 0.444 0.023 Uiso 1 1 calc R U . . .
C13 C -0.03149(15) 0.57282(13) 0.36687(7) 0.01416(19) Uani 1 1 d . . . . .
H13A H 0.0702 0.6338 0.4175 0.017 Uiso 1 1 calc R U . . .
H13B H -0.0799 0.6443 0.3487 0.017 Uiso 1 1 calc R U . . .
C14 C 0.38705(13) 0.76156(12) 0.35437(7) 0.01059(17) Uani 1 1 d . . . . .
H14 H 0.3439 0.8083 0.3997 0.013 Uiso 1 1 calc R U . . .
C15 C 0.43663(14) 0.64085(13) 0.39088(7) 0.01474(19) Uani 1 1 d . . . . .
H15A H 0.4689 0.5867 0.3443 0.018 Uiso 1 1 calc R U . . .
H15B H 0.3337 0.56 0.4071 0.018 Uiso 1 1 calc R U . . .
C16 C 0.59063(15) 0.71929(15) 0.47222(8) 0.0190(2) Uani 1 1 d . . . . .
H16A H 0.5538 0.7624 0.5212 0.023 Uiso 1 1 calc R U . . .
H16B H 0.6236 0.6389 0.4914 0.023 Uiso 1 1 calc R U . . .
C17 C 0.74944(15) 0.85233(14) 0.45240(8) 0.0178(2) Uani 1 1 d . . . . .
H17A H 0.8438 0.9046 0.5069 0.021 Uiso 1 1 calc R U . . .
H17B H 0.7943 0.8078 0.4078 0.021 Uiso 1 1 calc R U . . .
C18 C 0.70047(15) 0.97370(14) 0.41778(8) 0.0161(2) Uani 1 1 d . . . . .
H18A H 0.8036 1.0566 0.4029 0.019 Uiso 1 1 calc R U . . .
H18B H 0.6652 1.0249 0.4642 0.019 Uiso 1 1 calc R U . . .
C19 C 0.54952(14) 0.89454(13) 0.33568(7) 0.01378(19) Uani 1 1 d . . . . .
H19A H 0.5883 0.8504 0.2879 0.017 Uiso 1 1 calc R U . . .
H19B H 0.518 0.9748 0.315 0.017 Uiso 1 1 calc R U . . .
C20 C 0.12952(13) 0.81732(12) 0.23474(7) 0.01016(17) Uani 1 1 d . . . . .
H20 H -0.0005 0.7555 0.2121 0.012 Uiso 1 1 calc R U . . .
C21 C 0.15762(14) 0.94079(12) 0.31534(7) 0.01271(18) Uani 1 1 d . . . . .
H21A H 0.11 0.8864 0.3624 0.015 Uiso 1 1 calc R U . . .
H21B H 0.2849 1.0101 0.3387 0.015 Uiso 1 1 calc R U . . .
C22 C 0.06662(16) 1.04146(14) 0.29047(8) 0.0165(2) Uani 1 1 d . . . . .
H22A H -0.0618 0.9733 0.2724 0.02 Uiso 1 1 calc R U . . .
H22B H 0.0908 1.1227 0.3428 0.02 Uiso 1 1 calc R U . . .
C23 C 0.12934(18) 1.12250(14) 0.21529(8) 0.0210(2) Uani 1 1 d . . . . .
H23A H 0.2543 1.2015 0.2359 0.025 Uiso 1 1 calc R U . . .
H23B H 0.0608 1.1788 0.1976 0.025 Uiso 1 1 calc R U . . .
C24 C 0.10814(18) 1.00215(15) 0.13566(8) 0.0203(2) Uani 1 1 d . . . . .
H24A H -0.0183 0.9322 0.1102 0.024 Uiso 1 1 calc R U . . .
H24B H 0.159 1.0585 0.0899 0.024 Uiso 1 1 calc R U . . .
C25 C 0.19830(15) 0.90196(13) 0.16109(7) 0.01433(19) Uani 1 1 d . . . . .
H25A H 0.3264 0.9706 0.1812 0.017 Uiso 1 1 calc R U . . .
H25B H 0.1776 0.8225 0.1086 0.017 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 P1 2.0988(3) . ?
Ni1 C6 2.1192(11) . ?
Ni1 C5 2.1195(11) . ?
Ni1 C4 2.1262(11) . ?
Ni1 C2 2.1283(11) . ?
Ni1 C3 2.1343(11) . ?
Ni1 C1 2.1364(11) . ?
P1 C14 1.8644(10) . ?
P1 C8 1.8665(10) . ?
P1 C20 1.8812(10) . ?
C1 C2 1.4084(16) . ?
C1 C6 1.4143(17) . ?
C1 C7 1.5049(17) . ?
C2 C3 1.4089(16) . ?
C2 H2 0.95 . ?
C3 C4 1.4076(16) . ?
C3 H3 0.95 . ?
C4 C5 1.4101(18) . ?
C4 H4 0.95 . ?
C5 C6 1.4070(18) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 C13 1.5316(14) . ?
C8 C9 1.5344(14) . ?
C8 H8 1 . ?
C9 C10 1.5302(15) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.5256(17) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C12 1.5260(17) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 C13 1.5298(15) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 C15 1.5322(15) . ?
C14 C19 1.5361(15) . ?
C14 H14 1 . ?
C15 C16 1.5347(15) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 C17 1.5255(17) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 C18 1.5231(17) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 C19 1.5287(15) . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
C19 H19A 0.99 . ?
C19 H19B 0.99 . ?
C20 C25 1.5334(14) . ?
C20 C21 1.5375(14) . ?
C20 H20 1 . ?
C21 C22 1.5322(15) . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
C22 C23 1.5251(16) . ?
C22 H22A 0.99 . ?
C22 H22B 0.99 . ?
C23 C24 1.5275(17) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C24 C25 1.5250(16) . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
C25 H25A 0.99 . ?
C25 H25B 0.99 . ?

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
P1 Ni1 C6 134.80(3) . . ?
P1 Ni1 C5 139.85(3) . . ?
C6 Ni1 C5 38.77(5) . . ?
P1 Ni1 C4 143.62(3) . . ?
C6 Ni1 C4 70.17(5) . . ?
C5 Ni1 C4 38.79(5) . . ?
P1 Ni1 C2 136.95(3) . . ?
C6 Ni1 C2 69.60(4) . . ?
C5 Ni1 C2 82.67(4) . . ?
C4 Ni1 C2 69.88(4) . . ?
P1 Ni1 C3 142.14(3) . . ?
C6 Ni1 C3 82.74(4) . . ?
C5 Ni1 C3 69.87(5) . . ?
C4 Ni1 C3 38.58(4) . . ?
C2 Ni1 C3 38.60(4) . . ?
P1 Ni1 C1 132.84(3) . . ?
C6 Ni1 C1 38.82(4) . . ?
C5 Ni1 C1 70.43(5) . . ?
C4 Ni1 C1 83.52(4) . . ?
C2 Ni1 C1 38.57(4) . . ?
C3 Ni1 C1 70.18(4) . . ?
C14 P1 C8 101.89(5) . . ?
C14 P1 C20 104.14(5) . . ?
C8 P1 C20 102.58(5) . . ?
C14 P1 Ni1 114.42(3) . . ?
C8 P1 Ni1 117.00(3) . . ?
C20 P1 Ni1 114.98(3) . . ?
C2 C1 C6 118.36(11) . . ?
C2 C1 C7 120.15(11) . . ?
C6 C1 C7 121.48(11) . . ?
C2 C1 Ni1 70.40(6) . . ?
C6 C1 Ni1 69.93(6) . . ?
C7 C1 Ni1 132.19(8) . . ?
C1 C2 C3 121.24(10) . . ?
C1 C2 Ni1 71.03(6) . . ?
C3 C2 Ni1 70.93(6) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
Ni1 C2 H2 131.6 . . ?
C4 C3 C2 119.80(11) . . ?
C4 C3 Ni1 70.40(6) . . ?
C2 C3 Ni1 70.47(6) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
Ni1 C3 H3 131.9 . . ?
C3 C4 C5 119.67(11) . . ?
C3 C4 Ni1 71.02(6) . . ?
C5 C4 Ni1 70.35(7) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
Ni1 C4 H4 131.2 . . ?
C6 C5 C4 120.05(11) . . ?
C6 C5 Ni1 70.60(7) . . ?
C4 C5 Ni1 70.86(6) . . ?
C6 C5 H5 120 . . ?
C4 C5 H5 120 . . ?
Ni1 C5 H5 131.3 . . ?
C5 C6 C1 120.88(11) . . ?
C5 C6 Ni1 70.63(7) . . ?
C1 C6 Ni1 71.25(6) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
Ni1 C6 H6 131.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 110.25(9) . . ?
C13 C8 P1 116.94(7) . . ?
C9 C8 P1 110.50(7) . . ?
C13 C8 H8 106.1 . . ?
C9 C8 H8 106.1 . . ?
P1 C8 H8 106.1 . . ?
C10 C9 C8 111.65(9) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108 . . ?
C11 C10 C9 111.53(9) . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108 . . ?
C10 C11 C12 110.76(10) . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C13 110.59(10) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C8 111.28(9) . . ?
C12 C13 H13A 109.4 . . ?
C8 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C8 C13 H13B 109.4 . . ?
H13A C13 H13B 108 . . ?
C15 C14 C19 109.68(9) . . ?
C15 C14 P1 111.23(7) . . ?
C19 C14 P1 109.67(7) . . ?
C15 C14 H14 108.7 . . ?
C19 C14 H14 108.7 . . ?
P1 C14 H14 108.7 . . ?
C14 C15 C16 111.82(9) . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C15 111.44(9) . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 108 . . ?
C18 C17 C16 110.68(10) . . ?
C18 C17 H17A 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 C19 110.51(9) . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C18 C19 C14 111.80(9) . . ?
C18 C19 H19A 109.3 . . ?
C14 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
C14 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
C25 C20 C21 109.20(8) . . ?
C25 C20 P1 110.94(7) . . ?
C21 C20 P1 118.75(7) . . ?
C25 C20 H20 105.7 . . ?
C21 C20 H20 105.7 . . ?
P1 C20 H20 105.7 . . ?
C22 C21 C20 110.92(9) . . ?
C22 C21 H21A 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 108 . . ?
C23 C22 C21 111.71(9) . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 107.9 . . ?
C22 C23 C24 110.94(10) . . ?
C22 C23 H23A 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 108 . . ?
C25 C24 C23 111.59(10) . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24A 109.3 . . ?
C25 C24 H24B 109.3 . . ?
C23 C24 H24B 109.3 . . ?
H24A C24 H24B 108 . . ?
C24 C25 C20 111.41(9) . . ?
C24 C25 H25A 109.3 . . ?
C20 C25 H25A 109.3 . . ?
C24 C25 H25B 109.3 . . ?
C20 C25 H25B 109.3 . . ?
H25A C25 H25B 108 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1580332'
_audit_update_record             
;
2017-10-16 deposited with the CCDC.
2017-11-21 downloaded from the CCDC.
;

_audit_creation_date             2016-10-11T13:52:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C25 H38  F3  Ni1 P1'
_chemical_formula_sum            'C25 H38 F3 Ni P'
_chemical_formula_weight         485.23
_chemical_compound_source        synthesized

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.8792(7)
_cell_length_b                   9.2062(6)
_cell_length_c                   22.9722(15)
_cell_angle_alpha                90
_cell_angle_beta                 104.1810(10)
_cell_angle_gamma                90
_cell_volume                     2435.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9863
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      32.42
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014'
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.87
_shelx_estimated_absorpt_T_min   0.834
_shelx_estimated_absorpt_T_max   0.87

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_number            58452
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.107
_diffrn_reflns_theta_max         32.499
_diffrn_reflns_theta_full        32.499
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             8797
_reflns_number_gt                6886
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²+0.9472P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         8797
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.036
_refine_ls_wR_factor_ref         0.0904
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.072

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Ni Ni 0.3393 1.1124 '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'

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 0.26816(2) 0.50814(2) 0.07270(2) 0.02341(5) Uani 1 1 d . . . . .
P1 P 0.28634(3) 0.29010(3) 0.10371(2) 0.01594(6) Uani 1 1 d . . . . .
C1 C 0.22407(13) 0.62375(15) -0.00763(7) 0.0295(3) Uani 1 1 d . . . . .
C2 C 0.34113(15) 0.65204(18) 0.01994(8) 0.0397(4) Uani 1 1 d . . . . .
H2 H 0.39969 0.638945 -0.001289 0.048 Uiso 1 1 calc R U . . .
C3 C 0.3695(2) 0.70056(19) 0.08019(10) 0.0552(6) Uani 1 1 d . . . . .
H3 H 0.447941 0.720915 0.099926 0.066 Uiso 1 1 calc R U . . .
C4 C 0.2814(2) 0.71870(17) 0.11093(9) 0.0569(6) Uani 1 1 d . . . . .
H4 H 0.30111 0.749483 0.15164 0.068 Uiso 1 1 calc R U . . .
C5 C 0.1659(2) 0.69210(18) 0.08239(9) 0.0498(5) Uani 1 1 d . . . . .
H5 H 0.107124 0.70625 0.103418 0.06 Uiso 1 1 calc R U . . .
C6 C 0.13615(15) 0.64484(17) 0.02314(8) 0.0378(4) Uani 1 1 d . . . . .
H6 H 0.057231 0.626866 0.003505 0.045 Uiso 1 1 calc R U . . .
C7 C 0.19012(17) 0.57958(19) -0.07182(8) 0.0404(4) Uani 1 1 d . . . . .
C8 C 0.17717(10) 0.23616(13) 0.14572(5) 0.0181(2) Uani 1 1 d . . . . .
H8 H 0.09921 0.246157 0.117099 0.022 Uiso 1 1 calc R U . . .
C9 C 0.18507(12) 0.08013(14) 0.16911(6) 0.0241(3) Uani 1 1 d . . . . .
H9A H 0.176699 0.012156 0.134925 0.029 Uiso 1 1 calc R U . . .
H9B H 0.262531 0.064261 0.196491 0.029 Uiso 1 1 calc R U . . .
C10 C 0.09144(14) 0.04738(18) 0.20251(7) 0.0329(3) Uani 1 1 d . . . . .
H10A H 0.013962 0.05412 0.174224 0.039 Uiso 1 1 calc R U . . .
H10B H 0.101501 -0.053018 0.218381 0.039 Uiso 1 1 calc R U . . .
C11 C 0.09784(15) 0.1531(2) 0.25407(7) 0.0369(3) Uani 1 1 d . . . . .
H11A H 0.172445 0.140069 0.28428 0.044 Uiso 1 1 calc R U . . .
H11B H 0.034124 0.132381 0.273711 0.044 Uiso 1 1 calc R U . . .
C12 C 0.08802(13) 0.30924(18) 0.23145(6) 0.0319(3) Uani 1 1 d . . . . .
H12A H 0.097593 0.37627 0.266021 0.038 Uiso 1 1 calc R U . . .
H12B H 0.009712 0.325035 0.20492 0.038 Uiso 1 1 calc R U . . .
C13 C 0.17951(12) 0.34371(15) 0.19692(6) 0.0271(3) Uani 1 1 d . . . . .
H13A H 0.257362 0.34171 0.225035 0.033 Uiso 1 1 calc R U . . .
H13B H 0.166126 0.443045 0.180147 0.033 Uiso 1 1 calc R U . . .
C14 C 0.26792(10) 0.15183(13) 0.04316(5) 0.0180(2) Uani 1 1 d . . . . .
H14 H 0.284625 0.053502 0.061767 0.022 Uiso 1 1 calc R U . . .
C15 C 0.35299(12) 0.18221(15) 0.00401(6) 0.0241(2) Uani 1 1 d . . . . .
H15A H 0.342261 0.283197 -0.011152 0.029 Uiso 1 1 calc R U . . .
H15B H 0.433575 0.172631 0.028719 0.029 Uiso 1 1 calc R U . . .
C16 C 0.33449(14) 0.07709(18) -0.04929(7) 0.0319(3) Uani 1 1 d . . . . .
H16A H 0.388271 0.1025 -0.074518 0.038 Uiso 1 1 calc R U . . .
H16B H 0.352656 -0.023043 -0.034182 0.038 Uiso 1 1 calc R U . . .
C17 C 0.21003(14) 0.08293(19) -0.08727(7) 0.0343(3) Uani 1 1 d . . . . .
H17A H 0.199673 0.010819 -0.120132 0.041 Uiso 1 1 calc R U . . .
H17B H 0.193854 0.18052 -0.105508 0.041 Uiso 1 1 calc R U . . .
C18 C 0.12507(13) 0.05058(17) -0.04873(6) 0.0299(3) Uani 1 1 d . . . . .
H18A H 0.136356 -0.050553 -0.033793 0.036 Uiso 1 1 calc R U . . .
H18B H 0.044551 0.059695 -0.07357 0.036 Uiso 1 1 calc R U . . .
C19 C 0.14270(11) 0.15467(14) 0.00452(6) 0.0224(2) Uani 1 1 d . . . . .
H19A H 0.089144 0.127754 0.029674 0.027 Uiso 1 1 calc R U . . .
H19B H 0.123183 0.254583 -0.010524 0.027 Uiso 1 1 calc R U . . .
C20 C 0.42642(10) 0.24177(13) 0.15796(5) 0.0192(2) Uani 1 1 d . . . . .
H20 H 0.412211 0.25384 0.198827 0.023 Uiso 1 1 calc R U . . .
C21 C 0.47055(12) 0.08560(14) 0.15581(6) 0.0252(3) Uani 1 1 d . . . . .
H21A H 0.408606 0.016546 0.15923 0.03 Uiso 1 1 calc R U . . .
H21B H 0.489544 0.068612 0.116741 0.03 Uiso 1 1 calc R U . . .
C22 C 0.57839(13) 0.05800(18) 0.20669(8) 0.0354(3) Uani 1 1 d . . . . .
H22A H 0.557215 0.064743 0.245691 0.043 Uiso 1 1 calc R U . . .
H22B H 0.607305 -0.041546 0.202903 0.043 Uiso 1 1 calc R U . . .
C23 C 0.67437(13) 0.16678(19) 0.20566(8) 0.0368(3) Uani 1 1 d . . . . .
H23A H 0.739883 0.150968 0.241131 0.044 Uiso 1 1 calc R U . . .
H23B H 0.703241 0.150768 0.169232 0.044 Uiso 1 1 calc R U . . .
C24 C 0.63144(12) 0.32203(18) 0.20602(7) 0.0321(3) Uani 1 1 d . . . . .
H24A H 0.693847 0.389605 0.201895 0.038 Uiso 1 1 calc R U . . .
H24B H 0.612745 0.342084 0.244946 0.038 Uiso 1 1 calc R U . . .
C25 C 0.52366(11) 0.34906(15) 0.15504(6) 0.0251(3) Uani 1 1 d . . . . .
H25A H 0.544174 0.338647 0.115994 0.03 Uiso 1 1 calc R U . . .
H25B H 0.49586 0.449592 0.157833 0.03 Uiso 1 1 calc R U . . .
F1 F 0.17079(13) 0.69518(13) -0.10876(5) 0.0622(3) Uani 1 1 d . . . . .
F2 F 0.09309(12) 0.50045(14) -0.08613(6) 0.0650(4) Uani 1 1 d . . . . .
F3 F 0.27146(14) 0.50084(13) -0.08877(6) 0.0629(4) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C1 2.0831(14) . ?
NI1 C6 2.1130(15) . ?
NI1 C4 2.1180(17) . ?
NI1 C2 2.1190(16) . ?
NI1 P1 2.1232(4) . ?
NI1 C3 2.1248(17) . ?
NI1 C5 2.1276(17) . ?
P1 C14 1.8585(12) . ?
P1 C8 1.8636(12) . ?
P1 C20 1.8718(12) . ?
C1 C2 1.404(2) . ?
C1 C6 1.411(2) . ?
C1 C7 1.487(2) . ?
C2 C3 1.414(3) . ?
C2 H2 0.95 . ?
C3 C4 1.409(3) . ?
C3 H3 0.95 . ?
C4 C5 1.390(3) . ?
C4 H4 0.95 . ?
C5 C6 1.390(3) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 F2 1.335(2) . ?
C7 F3 1.340(2) . ?
C7 F1 1.3453(18) . ?
C8 C9 1.5284(18) . ?
C8 C13 1.5325(17) . ?
C8 H8 1 . ?
C9 C10 1.5279(19) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.520(2) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C12 1.523(2) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 C13 1.528(2) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 C15 1.5342(17) . ?
C14 C19 1.5343(17) . ?
C14 H14 1 . ?
C15 C16 1.5336(19) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 C17 1.523(2) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 C18 1.526(2) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 C19 1.5275(18) . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
C19 H19A 0.99 . ?
C19 H19B 0.99 . ?
C20 C25 1.5337(18) . ?
C20 C21 1.5353(18) . ?
C20 H20 1 . ?
C21 C22 1.529(2) . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
C22 C23 1.522(2) . ?
C22 H22A 0.99 . ?
C22 H22B 0.99 . ?
C23 C24 1.518(2) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C24 C25 1.5291(19) . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
C25 H25A 0.99 . ?
C25 H25B 0.99 . ?

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
C1 NI1 C6 39.28(6) . . ?
C1 NI1 C4 82.92(7) . . ?
C6 NI1 C4 69.40(8) . . ?
C1 NI1 C2 39.03(6) . . ?
C6 NI1 C2 70.91(7) . . ?
C4 NI1 C2 70.48(8) . . ?
C1 NI1 P1 139.74(4) . . ?
C6 NI1 P1 138.15(5) . . ?
C4 NI1 P1 137.32(5) . . ?
C2 NI1 P1 139.53(5) . . ?
C1 NI1 C3 70.14(7) . . ?
C6 NI1 C3 82.99(7) . . ?
C4 NI1 C3 38.78(9) . . ?
C2 NI1 C3 38.93(8) . . ?
P1 NI1 C3 138.77(6) . . ?
C1 NI1 C5 70.11(7) . . ?
C6 NI1 C5 38.26(7) . . ?
C4 NI1 C5 38.21(9) . . ?
C2 NI1 C5 83.47(8) . . ?
P1 NI1 C5 136.99(6) . . ?
C3 NI1 C5 69.80(9) . . ?
C14 P1 C8 103.64(5) . . ?
C14 P1 C20 104.95(5) . . ?
C8 P1 C20 102.11(5) . . ?
C14 P1 NI1 114.38(4) . . ?
C8 P1 NI1 113.52(4) . . ?
C20 P1 NI1 116.67(4) . . ?
C2 C1 C6 121.43(16) . . ?
C2 C1 C7 119.74(15) . . ?
C6 C1 C7 118.71(15) . . ?
C2 C1 NI1 71.87(9) . . ?
C6 C1 NI1 71.50(9) . . ?
C7 C1 NI1 133.40(11) . . ?
C1 C2 C3 118.17(18) . . ?
C1 C2 NI1 69.11(8) . . ?
C3 C2 NI1 70.75(10) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
NI1 C2 H2 131.9 . . ?
C4 C3 C2 120.00(18) . . ?
C4 C3 NI1 70.35(10) . . ?
C2 C3 NI1 70.32(9) . . ?
C4 C3 H3 120 . . ?
C2 C3 H3 120 . . ?
NI1 C3 H3 132.3 . . ?
C5 C4 C3 120.76(18) . . ?
C5 C4 NI1 71.27(10) . . ?
C3 C4 NI1 70.87(10) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
NI1 C4 H4 131 . . ?
C6 C5 C4 120.12(19) . . ?
C6 C5 NI1 70.30(9) . . ?
C4 C5 NI1 70.52(11) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
NI1 C5 H5 132.2 . . ?
C5 C6 C1 119.49(17) . . ?
C5 C6 NI1 71.44(10) . . ?
C1 C6 NI1 69.22(8) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
NI1 C6 H6 131.9 . . ?
F2 C7 F3 105.90(16) . . ?
F2 C7 F1 105.83(15) . . ?
F3 C7 F1 105.57(14) . . ?
F2 C7 C1 113.67(14) . . ?
F3 C7 C1 113.36(15) . . ?
F1 C7 C1 111.85(15) . . ?
C9 C8 C13 110.44(10) . . ?
C9 C8 P1 116.23(8) . . ?
C13 C8 P1 109.95(9) . . ?
C9 C8 H8 106.6 . . ?
C13 C8 H8 106.6 . . ?
P1 C8 H8 106.6 . . ?
C10 C9 C8 111.87(12) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 111.17(12) . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108 . . ?
C10 C11 C12 110.69(12) . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C13 111.61(12) . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108 . . ?
C12 C13 C8 112.51(11) . . ?
C12 C13 H13A 109.1 . . ?
C8 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
C8 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C19 110.02(10) . . ?
C15 C14 P1 109.89(8) . . ?
C19 C14 P1 109.94(8) . . ?
C15 C14 H14 109 . . ?
C19 C14 H14 109 . . ?
P1 C14 H14 109 . . ?
C16 C15 C14 111.52(11) . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108 . . ?
C17 C16 C15 111.37(12) . . ?
C17 C16 H16A 109.4 . . ?
C15 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108 . . ?
C16 C17 C18 110.36(12) . . ?
C16 C17 H17A 109.6 . . ?
C18 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
C18 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 C19 111.21(12) . . ?
C17 C18 H18A 109.4 . . ?
C19 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
C19 C18 H18B 109.4 . . ?
H18A C18 H18B 108 . . ?
C18 C19 C14 112.08(11) . . ?
C18 C19 H19A 109.2 . . ?
C14 C19 H19A 109.2 . . ?
C18 C19 H19B 109.2 . . ?
C14 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C25 C20 C21 109.57(10) . . ?
C25 C20 P1 111.96(9) . . ?
C21 C20 P1 117.13(9) . . ?
C25 C20 H20 105.8 . . ?
C21 C20 H20 105.8 . . ?
P1 C20 H20 105.8 . . ?
C22 C21 C20 111.09(12) . . ?
C22 C21 H21A 109.4 . . ?
C20 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C20 C21 H21B 109.4 . . ?
H21A C21 H21B 108 . . ?
C23 C22 C21 111.67(13) . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 107.9 . . ?
C24 C23 C22 111.43(13) . . ?
C24 C23 H23A 109.3 . . ?
C22 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
C22 C23 H23B 109.3 . . ?
H23A C23 H23B 108 . . ?
C23 C24 C25 111.61(12) . . ?
C23 C24 H24A 109.3 . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24B 109.3 . . ?
C25 C24 H24B 109.3 . . ?
H24A C24 H24B 108 . . ?
C24 C25 C20 111.10(11) . . ?
C24 C25 H25A 109.4 . . ?
C20 C25 H25A 109.4 . . ?
C24 C25 H25B 109.4 . . ?
C20 C25 H25B 109.4 . . ?
H25A C25 H25B 108 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
