# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_mcbc160801
_database_code_depnum_ccdc_archive 'CCDC 1867496'
_audit_update_record             
;
2018-09-13 deposited with the CCDC.
2018-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H31 Br N2 Ni S'
_chemical_formula_sum            'C23 H31 Br N2 Ni S'
_chemical_formula_weight         506.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5279(3)
_cell_length_b                   12.2430(4)
_cell_length_c                   12.4761(4)
_cell_angle_alpha                105.1400(10)
_cell_angle_beta                 111.7710(10)
_cell_angle_gamma                105.4150(10)
_cell_volume                     1193.08(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9536
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      32.00

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    2.586
_shelx_estimated_absorpt_T_min   0.424
_shelx_estimated_absorpt_T_max   0.511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6724
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38832
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.884
_diffrn_reflns_theta_max         32.016
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8196
_reflns_number_gt                6747
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0412P)²+1.2454P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8196
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0937
_refine_ls_wR_factor_gt          0.0849
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5378(2) 0.72264(15) 0.69044(16) 0.0202(3) Uani 1 1 d . . . . .
C2 C 0.7400(2) 0.65257(17) 0.71060(19) 0.0269(3) Uani 1 1 d . . . . .
H2 H 0.7937 0.5975 0.7075 0.032 Uiso 1 1 calc R U . . .
C3 C 0.8107(2) 0.77642(18) 0.75091(19) 0.0284(4) Uani 1 1 d . . . . .
H3 H 0.9241 0.8257 0.7818 0.034 Uiso 1 1 calc R U . . .
C4 C 0.4522(2) 0.49498(15) 0.62497(17) 0.0243(3) Uani 1 1 d . . . . .
H4A H 0.4850 0.4370 0.5781 0.029 Uiso 1 1 calc R U . . .
H4B H 0.3433 0.4875 0.5652 0.029 Uiso 1 1 calc R U . . .
C5 C 0.4368(3) 0.45933(19) 0.7286(2) 0.0358(4) Uani 1 1 d . . . . .
H5A H 0.4114 0.5195 0.7803 0.043 Uiso 1 1 calc R U . . .
H5B H 0.5409 0.4570 0.7840 0.043 Uiso 1 1 calc R U . . .
C6 C 0.2439(3) 0.2740(3) 0.7766(3) 0.0498(7) Uani 1 1 d . . . . .
C7 C 0.1895(6) 0.3640(4) 0.8408(4) 0.0885(14) Uani 1 1 d . . . . .
H7A H 0.0895 0.3632 0.7779 0.133 Uiso 1 1 calc R U . . .
H7B H 0.2776 0.4474 0.8828 0.133 Uiso 1 1 calc R U . . .
H7C H 0.1661 0.3399 0.9033 0.133 Uiso 1 1 calc R U . . .
C8 C 0.1018(5) 0.1446(3) 0.7063(4) 0.0753(11) Uani 1 1 d . . . . .
H8A H 0.0733 0.1194 0.7665 0.113 Uiso 1 1 calc R U . . .
H8B H 0.1363 0.0853 0.6649 0.113 Uiso 1 1 calc R U . . .
H8C H 0.0051 0.1468 0.6428 0.113 Uiso 1 1 calc R U . . .
C9 C 0.4010(8) 0.2924(6) 0.8922(6) 0.0671(19) Uani 0.6 1 d . . P A 1
H9A H 0.4888 0.3733 0.9209 0.101 Uiso 0.6 1 calc R U P A 1
H9B H 0.4381 0.2270 0.8680 0.101 Uiso 0.6 1 calc R U P A 1
H9C H 0.3750 0.2886 0.9605 0.101 Uiso 0.6 1 calc R U P A 1
C9B C 0.3878(12) 0.2346(10) 0.8254(10) 0.0671(19) Uani 0.4 1 d . . P A 2
H9D H 0.4927 0.3077 0.8715 0.101 Uiso 0.4 1 calc R U P A 2
H9E H 0.3868 0.1763 0.7540 0.101 Uiso 0.4 1 calc R U P A 2
H9F H 0.3755 0.1946 0.8819 0.101 Uiso 0.4 1 calc R U P A 2
C10 C 0.7168(2) 0.94777(15) 0.78325(17) 0.0218(3) Uani 1 1 d . . . . .
C11 C 0.7021(2) 1.00616(16) 0.69966(18) 0.0257(3) Uani 1 1 d . . . . .
C12 C 0.7374(3) 1.13228(18) 0.7479(2) 0.0312(4) Uani 1 1 d . . . . .
H12 H 0.7273 1.1743 0.6931 0.037 Uiso 1 1 calc R U . . .
C13 C 0.7870(3) 1.19812(17) 0.8739(2) 0.0316(4) Uani 1 1 d . . . . .
C14 C 0.8006(3) 1.13657(17) 0.9540(2) 0.0299(4) Uani 1 1 d . . . . .
H14 H 0.8337 1.1811 1.0402 0.036 Uiso 1 1 calc R U . . .
C15 C 0.7666(2) 1.01051(16) 0.91030(17) 0.0244(3) Uani 1 1 d . . . . .
C16 C 0.6568(3) 0.9371(2) 0.56471(19) 0.0363(5) Uani 1 1 d . . . . .
H16A H 0.7392 0.9043 0.5618 0.054 Uiso 1 1 calc R U . . .
H16B H 0.6539 0.9934 0.5215 0.054 Uiso 1 1 calc R U . . .
H16C H 0.5478 0.8687 0.5228 0.054 Uiso 1 1 calc R U . . .
C17 C 0.8306(4) 1.3358(2) 0.9247(3) 0.0497(6) Uani 1 1 d . . . . .
H17A H 0.7943 1.3573 0.9882 0.075 Uiso 1 1 calc R U . . .
H17B H 0.7753 1.3582 0.8555 0.075 Uiso 1 1 calc R U . . .
H17C H 0.9505 1.3810 0.9631 0.075 Uiso 1 1 calc R U . . .
C18 C 0.7869(3) 0.9456(2) 0.9988(2) 0.0343(4) Uani 1 1 d . . . . .
H18A H 0.7010 0.8611 0.9545 0.051 Uiso 1 1 calc R U . . .
H18B H 0.7768 0.9907 1.0711 0.051 Uiso 1 1 calc R U . . .
H18C H 0.8960 0.9427 1.0283 0.051 Uiso 1 1 calc R U . . .
C19 C 0.1745(4) 0.6656(3) 0.7267(3) 0.0535(7) Uani 1 1 d . . . . .
H19 H 0.1370 0.5880 0.7318 0.064 Uiso 1 1 calc R U . . .
C20 C 0.3242(4) 0.7662(4) 0.8113(3) 0.0657(10) Uani 1 1 d . . . . .
H20 H 0.4122 0.7665 0.8800 0.079 Uiso 1 1 calc R U . . .
C21 C 0.3236(4) 0.8693(3) 0.7777(4) 0.0715(11) Uani 1 1 d . . . . .
H21 H 0.4061 0.9515 0.8231 0.086 Uiso 1 1 calc R U . . .
C22 C 0.1803(4) 0.8261(3) 0.6669(4) 0.0613(8) Uani 1 1 d . . . . .
H22 H 0.1465 0.8727 0.6201 0.074 Uiso 1 1 calc R U . . .
C23 C 0.0922(3) 0.6998(3) 0.6352(3) 0.0503(6) Uani 1 1 d . . . . .
H23 H -0.0094 0.6466 0.5610 0.060 Uiso 1 1 calc R U . . .
N1 N 0.57380(19) 0.62126(13) 0.67448(14) 0.0216(3) Uani 1 1 d . . . . .
N2 N 0.68603(19) 0.81831(13) 0.73872(15) 0.0223(3) Uani 1 1 d . . . . .
S1 S 0.27008(11) 0.30796(6) 0.65042(7) 0.0578(2) Uani 1 1 d . . . . .
Ni1 Ni 0.32654(3) 0.72384(2) 0.64276(2) 0.02320(6) Uani 1 1 d . . . . .
Br1 Br 0.24064(3) 0.64664(2) 0.42698(2) 0.02990(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.359(2) . ?
C1 N2 1.360(2) . ?
C1 Ni1 1.8805(18) . ?
C2 C3 1.347(3) . ?
C2 N1 1.384(2) . ?
C2 H2 0.9500 . ?
C3 N2 1.389(2) . ?
C3 H3 0.9500 . ?
C4 N1 1.460(2) . ?
C4 C5 1.511(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 S1 1.803(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.508(5) . ?
C6 C8 1.537(4) . ?
C6 C9B 1.539(11) . ?
C6 C9 1.556(6) . ?
C6 S1 1.814(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9B H9D 0.9800 . ?
C9B H9E 0.9800 . ?
C9B H9F 0.9800 . ?
C10 C15 1.393(2) . ?
C10 C11 1.397(2) . ?
C10 N2 1.442(2) . ?
C11 C12 1.396(3) . ?
C11 C16 1.503(3) . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(3) . ?
C13 C17 1.513(3) . ?
C14 C15 1.396(3) . ?
C14 H14 0.9500 . ?
C15 C18 1.506(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C23 1.361(4) . ?
C19 C20 1.392(5) . ?
C19 Ni1 2.161(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.430(6) . ?
C20 Ni1 2.040(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.375(5) . ?
C21 Ni1 2.122(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.413(5) . ?
C22 Ni1 2.155(2) . ?
C22 H22 0.9500 . ?
C23 Ni1 2.136(2) . ?
C23 H23 0.9500 . ?
Ni1 Br1 2.3314(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 103.95(15) . . ?
N1 C1 Ni1 126.53(13) . . ?
N2 C1 Ni1 129.35(12) . . ?
C3 C2 N1 106.55(16) . . ?
C3 C2 H2 126.7 . . ?
N1 C2 H2 126.7 . . ?
C2 C3 N2 106.80(17) . . ?
C2 C3 H3 126.6 . . ?
N2 C3 H3 126.6 . . ?
N1 C4 C5 111.96(15) . . ?
N1 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
N1 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 S1 105.94(14) . . ?
C4 C5 H5A 110.5 . . ?
S1 C5 H5A 110.5 . . ?
C4 C5 H5B 110.5 . . ?
S1 C5 H5B 110.5 . . ?
H5A C5 H5B 108.7 . . ?
C7 C6 C8 108.9(3) . . ?
C7 C6 C9B 133.1(5) . . ?
C8 C6 C9B 98.0(4) . . ?
C7 C6 C9 100.0(4) . . ?
C8 C6 C9 116.8(3) . . ?
C7 C6 S1 110.5(2) . . ?
C8 C6 S1 103.0(2) . . ?
C9B C6 S1 99.5(4) . . ?
C9 C6 S1 117.6(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C9B H9D 109.5 . . ?
C6 C9B H9E 109.5 . . ?
H9D C9B H9E 109.5 . . ?
C6 C9B H9F 109.5 . . ?
H9D C9B H9F 109.5 . . ?
H9E C9B H9F 109.5 . . ?
C15 C10 C11 122.75(16) . . ?
C15 C10 N2 117.89(15) . . ?
C11 C10 N2 119.31(15) . . ?
C12 C11 C10 117.20(17) . . ?
C12 C11 C16 121.41(18) . . ?
C10 C11 C16 121.35(16) . . ?
C13 C12 C11 121.82(18) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C14 119.13(17) . . ?
C12 C13 C17 120.6(2) . . ?
C14 C13 C17 120.2(2) . . ?
C13 C14 C15 121.22(18) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C10 C15 C14 117.87(17) . . ?
C10 C15 C18 121.35(16) . . ?
C14 C15 C18 120.77(17) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C23 C19 C20 106.8(3) . . ?
C23 C19 Ni1 70.52(15) . . ?
C20 C19 Ni1 66.04(15) . . ?
C23 C19 H19 126.6 . . ?
C20 C19 H19 126.6 . . ?
Ni1 C19 H19 128.3 . . ?
C19 C20 C21 108.7(3) . . ?
C19 C20 Ni1 75.41(16) . . ?
C21 C20 Ni1 73.01(17) . . ?
C19 C20 H20 125.7 . . ?
C21 C20 H20 125.6 . . ?
Ni1 C20 H20 117.8 . . ?
C22 C21 C20 106.5(3) . . ?
C22 C21 Ni1 72.54(16) . . ?
C20 C21 Ni1 66.85(14) . . ?
C22 C21 H21 126.7 . . ?
C20 C21 H21 126.7 . . ?
Ni1 C21 H21 125.4 . . ?
C21 C22 C23 107.6(3) . . ?
C21 C22 Ni1 69.98(15) . . ?
C23 C22 Ni1 70.04(14) . . ?
C21 C22 H22 126.2 . . ?
C23 C22 H22 126.2 . . ?
Ni1 C22 H22 125.4 . . ?
C19 C23 C22 109.9(3) . . ?
C19 C23 Ni1 72.54(15) . . ?
C22 C23 Ni1 71.50(15) . . ?
C19 C23 H23 125.1 . . ?
C22 C23 H23 125.1 . . ?
Ni1 C23 H23 122.5 . . ?
C1 N1 C2 111.57(15) . . ?
C1 N1 C4 124.21(15) . . ?
C2 N1 C4 124.22(15) . . ?
C1 N2 C3 111.13(15) . . ?
C1 N2 C10 125.64(15) . . ?
C3 N2 C10 123.00(15) . . ?
C5 S1 C6 104.65(13) . . ?
C1 Ni1 C20 100.76(10) . . ?
C1 Ni1 C21 112.93(11) . . ?
C20 Ni1 C21 40.13(16) . . ?
C1 Ni1 C23 160.60(10) . . ?
C20 Ni1 C23 63.86(12) . . ?
C21 Ni1 C23 63.80(12) . . ?
C1 Ni1 C22 147.83(12) . . ?
C20 Ni1 C22 64.74(14) . . ?
C21 Ni1 C22 37.49(14) . . ?
C23 Ni1 C22 38.46(12) . . ?
C1 Ni1 C19 123.68(10) . . ?
C20 Ni1 C19 38.55(14) . . ?
C21 Ni1 C19 64.74(13) . . ?
C23 Ni1 C19 36.93(12) . . ?
C22 Ni1 C19 63.50(12) . . ?
C1 Ni1 Br1 95.31(5) . . ?
C20 Ni1 Br1 162.08(10) . . ?
C21 Ni1 Br1 137.75(13) . . ?
C23 Ni1 Br1 98.70(8) . . ?
C22 Ni1 Br1 104.73(10) . . ?
C19 Ni1 Br1 124.45(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 0.1(2) . . . . ?
N1 C4 C5 S1 174.87(14) . . . . ?
C15 C10 C11 C12 -1.0(3) . . . . ?
N2 C10 C11 C12 -178.32(17) . . . . ?
C15 C10 C11 C16 176.68(19) . . . . ?
N2 C10 C11 C16 -0.7(3) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C16 C11 C12 C13 -176.9(2) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C11 C12 C13 C17 177.7(2) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C17 C13 C14 C15 -177.7(2) . . . . ?
C11 C10 C15 C14 0.9(3) . . . . ?
N2 C10 C15 C14 178.35(17) . . . . ?
C11 C10 C15 C18 -177.83(19) . . . . ?
N2 C10 C15 C18 -0.4(3) . . . . ?
C13 C14 C15 C10 -0.7(3) . . . . ?
C13 C14 C15 C18 178.1(2) . . . . ?
C23 C19 C20 C21 7.0(3) . . . . ?
Ni1 C19 C20 C21 65.99(18) . . . . ?
C23 C19 C20 Ni1 -58.98(19) . . . . ?
C19 C20 C21 C22 -5.4(3) . . . . ?
Ni1 C20 C21 C22 62.1(2) . . . . ?
C19 C20 C21 Ni1 -67.58(18) . . . . ?
C20 C21 C22 C23 1.7(3) . . . . ?
Ni1 C21 C22 C23 60.20(19) . . . . ?
C20 C21 C22 Ni1 -58.45(17) . . . . ?
C20 C19 C23 C22 -6.0(3) . . . . ?
Ni1 C19 C23 C22 -62.13(18) . . . . ?
C20 C19 C23 Ni1 56.17(17) . . . . ?
C21 C22 C23 C19 2.6(3) . . . . ?
Ni1 C22 C23 C19 62.78(18) . . . . ?
C21 C22 C23 Ni1 -60.16(19) . . . . ?
N2 C1 N1 C2 -0.63(19) . . . . ?
Ni1 C1 N1 C2 174.97(13) . . . . ?
N2 C1 N1 C4 179.58(15) . . . . ?
Ni1 C1 N1 C4 -4.8(2) . . . . ?
C3 C2 N1 C1 0.4(2) . . . . ?
C3 C2 N1 C4 -179.85(17) . . . . ?
C5 C4 N1 C1 -90.5(2) . . . . ?
C5 C4 N1 C2 89.7(2) . . . . ?
N1 C1 N2 C3 0.67(19) . . . . ?
Ni1 C1 N2 C3 -174.75(14) . . . . ?
N1 C1 N2 C10 -173.89(15) . . . . ?
Ni1 C1 N2 C10 10.7(3) . . . . ?
C2 C3 N2 C1 -0.5(2) . . . . ?
C2 C3 N2 C10 174.25(17) . . . . ?
C15 C10 N2 C1 91.3(2) . . . . ?
C11 C10 N2 C1 -91.2(2) . . . . ?
C15 C10 N2 C3 -82.7(2) . . . . ?
C11 C10 N2 C3 94.8(2) . . . . ?
C4 C5 S1 C6 -175.39(16) . . . . ?
C7 C6 S1 C5 64.0(3) . . . . ?
C8 C6 S1 C5 -179.8(2) . . . . ?
C9B C6 S1 C5 -79.2(4) . . . . ?
C9 C6 S1 C5 -49.8(4) . . . . ?
N1 C1 Ni1 C20 99.95(19) . . . . ?
N2 C1 Ni1 C20 -85.6(2) . . . . ?
N1 C1 Ni1 C21 140.08(19) . . . . ?
N2 C1 Ni1 C21 -45.5(2) . . . . ?
N1 C1 Ni1 C23 64.1(3) . . . . ?
N2 C1 Ni1 C23 -121.5(3) . . . . ?
N1 C1 Ni1 C22 159.1(2) . . . . ?
N2 C1 Ni1 C22 -26.5(3) . . . . ?
N1 C1 Ni1 C19 66.04(19) . . . . ?
N2 C1 Ni1 C19 -119.49(18) . . . . ?
N1 C1 Ni1 Br1 -72.09(15) . . . . ?
N2 C1 Ni1 Br1 102.38(15) . . . . ?

_refine_diff_density_max         1.711
_refine_diff_density_min         -1.821
_refine_diff_density_rms         0.078

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene/n-hexane'
####################################################################### 
# 
# 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_mcfu170809
_database_code_depnum_ccdc_archive 'CCDC 1867503'
_audit_update_record             
;
2018-09-13 deposited with the CCDC.
2018-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H27 N2 Ni S, F6 P'
_chemical_formula_sum            'C21 H27 F6 N2 Ni P S'
_chemical_formula_weight         543.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.2425(2)
_cell_length_b                   15.5464(4)
_cell_length_c                   16.5839(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.4090(10)
_cell_angle_gamma                90
_cell_volume                     2372.29(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9973
_cell_measurement_theta_min      3.91
_cell_measurement_theta_max      66.61

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    3.178
_shelx_estimated_absorpt_T_min   0.598
_shelx_estimated_absorpt_T_max   0.785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6494
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_source                   'Cu-ImuS microfocus tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23312
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.905
_diffrn_reflns_theta_max         66.698
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             4166
_reflns_number_gt                3634
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0700P)²+5.3540P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4166
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1510
_refine_ls_wR_factor_gt          0.1446
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5410(3) 0.5655(2) 0.14022(18) 0.0281(7) Uani 1 1 d . . . . .
C2 C 0.4803(4) 0.4369(2) 0.0846(2) 0.0388(8) Uani 1 1 d . . . . .
H2 H 0.4233 0.3912 0.0605 0.047 Uiso 1 1 calc R U . . .
C3 C 0.6240(4) 0.4367(2) 0.1034(2) 0.0371(8) Uani 1 1 d . . . . .
H3 H 0.6889 0.3908 0.0952 0.044 Uiso 1 1 calc R U . . .
C4 C 0.2797(4) 0.5452(3) 0.0968(2) 0.0426(9) Uani 1 1 d . . . . .
H4A H 0.2202 0.5029 0.0636 0.051 Uiso 1 1 calc R U . . .
H4B H 0.2740 0.6009 0.0678 0.051 Uiso 1 1 calc R U . . .
C5 C 0.2197(4) 0.5554(3) 0.1780(3) 0.0528(11) Uani 1 1 d . . . . .
H5A H 0.2317 0.5007 0.2084 0.063 Uiso 1 1 calc R U . . .
H5B H 0.1144 0.5682 0.1693 0.063 Uiso 1 1 calc R U . . .
C6 C 0.3559(4) 0.5915(2) 0.3387(2) 0.0400(8) Uani 1 1 d . . . . .
C7 C 0.2127(5) 0.5711(3) 0.3731(3) 0.0599(12) Uani 1 1 d . . . . .
H7A H 0.1607 0.5268 0.3399 0.090 Uiso 1 1 calc R U . . .
H7B H 0.1531 0.6233 0.3728 0.090 Uiso 1 1 calc R U . . .
H7C H 0.2321 0.5501 0.4288 0.090 Uiso 1 1 calc R U . . .
C8 C 0.4476(5) 0.5111(3) 0.3334(3) 0.0537(11) Uani 1 1 d . . . . .
H8A H 0.4746 0.4887 0.3879 0.081 Uiso 1 1 calc R U . . .
H8B H 0.5357 0.5252 0.3075 0.081 Uiso 1 1 calc R U . . .
H8C H 0.3916 0.4675 0.3011 0.081 Uiso 1 1 calc R U . . .
C9 C 0.4403(6) 0.6607(3) 0.3883(3) 0.0683(14) Uani 1 1 d . . . . .
H9A H 0.4654 0.6398 0.4435 0.103 Uiso 1 1 calc R U . . .
H9B H 0.3804 0.7126 0.3898 0.103 Uiso 1 1 calc R U . . .
H9C H 0.5295 0.6744 0.3633 0.103 Uiso 1 1 calc R U . . .
C10 C 0.8098(3) 0.5383(2) 0.1698(2) 0.0338(8) Uani 1 1 d . . . . .
H10A H 0.8201 0.6016 0.1728 0.041 Uiso 1 1 calc R U . . .
H10B H 0.8792 0.5163 0.1328 0.041 Uiso 1 1 calc R U . . .
C11 C 0.8466(3) 0.5004(2) 0.2532(2) 0.0325(7) Uani 1 1 d . . . . .
C12 C 0.8290(4) 0.5493(3) 0.3216(2) 0.0392(8) Uani 1 1 d . . . . .
H12 H 0.7979 0.6074 0.3159 0.047 Uiso 1 1 calc R U . . .
C13 C 0.8564(4) 0.5136(3) 0.3983(2) 0.0478(10) Uani 1 1 d . . . . .
H13 H 0.8433 0.5473 0.4448 0.057 Uiso 1 1 calc R U . . .
C14 C 0.9027(4) 0.4297(3) 0.4071(2) 0.0483(10) Uani 1 1 d . . . . .
H14 H 0.9205 0.4052 0.4596 0.058 Uiso 1 1 calc R U . . .
C15 C 0.9232(4) 0.3812(3) 0.3392(3) 0.0480(10) Uani 1 1 d . . . . .
H15 H 0.9567 0.3236 0.3451 0.058 Uiso 1 1 calc R U . . .
C16 C 0.8948(4) 0.4166(2) 0.2625(2) 0.0394(8) Uani 1 1 d . . . . .
H16 H 0.9087 0.3829 0.2160 0.047 Uiso 1 1 calc R U . . .
C17 C 0.4796(6) 0.8067(3) 0.2040(3) 0.0555(12) Uani 1 1 d . . . . .
H17 H 0.4107 0.8249 0.2395 0.067 Uiso 1 1 calc R U . . .
C18 C 0.6254(6) 0.7845(3) 0.2270(3) 0.0694(16) Uani 1 1 d . . . . .
H18 H 0.6750 0.7890 0.2797 0.083 Uiso 1 1 calc R U . . .
C19 C 0.6823(5) 0.7548(3) 0.1577(4) 0.0681(16) Uani 1 1 d . . . . .
H19 H 0.7775 0.7327 0.1547 0.082 Uiso 1 1 calc R U . . .
C20 C 0.5740(6) 0.7633(3) 0.0924(3) 0.0561(12) Uani 1 1 d . . . . .
H20 H 0.5841 0.7477 0.0378 0.067 Uiso 1 1 calc R U . . .
C21 C 0.4535(5) 0.7974(3) 0.1199(3) 0.0506(10) Uani 1 1 d . . . . .
H21 H 0.3665 0.8123 0.0879 0.061 Uiso 1 1 calc R U . . .
N1 N 0.4307(3) 0.51612(19) 0.10684(17) 0.0335(6) Uani 1 1 d . . . . .
N2 N 0.6605(3) 0.51630(18) 0.13717(16) 0.0292(6) Uani 1 1 d . . . . .
F1 F 0.8161(4) 0.6500(3) 0.0034(3) 0.0703(11) Uani 0.7 1 d . . P A 1
F2 F 1.0315(6) 0.6957(4) 0.0552(4) 0.0910(10) Uani 0.7 1 d . . P A 1
F3 F 1.1060(6) 0.7128(4) -0.0661(4) 0.0910(10) Uani 0.7 1 d . . P A 1
F4 F 0.8755(7) 0.6678(4) -0.1209(3) 0.1024(19) Uani 0.7 1 d . . P A 1
F1B F 0.7966(11) 0.6754(7) -0.0526(7) 0.0703(11) Uani 0.3 1 d . . P A 2
F2B F 0.9728(15) 0.6719(9) 0.0593(10) 0.0910(10) Uani 0.3 1 d . . P A 2
F3B F 1.1256(14) 0.7306(9) -0.0190(9) 0.0910(10) Uani 0.3 1 d . . P A 2
F4B F 0.9673(15) 0.7302(11) -0.1293(6) 0.1024(19) Uani 0.3 1 d . . P A 2
F5 F 1.0163(3) 0.5942(2) -0.0430(2) 0.0927(11) Uani 1 1 d . . . . .
F6 F 0.9028(4) 0.7835(2) -0.0247(3) 0.1057(13) Uani 1 1 d . . . . .
P1 P 0.95724(11) 0.68914(7) -0.03622(7) 0.0461(3) Uani 1 1 d . . . . .
S1 S 0.31080(9) 0.64137(6) 0.23786(6) 0.0370(2) Uani 1 1 d . . . . .
Ni1 Ni 0.50385(6) 0.67687(4) 0.17927(3) 0.0306(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.349(4) . ?
C1 N1 1.353(4) . ?
C1 Ni1 1.891(3) . ?
C2 C3 1.336(5) . ?
C2 N1 1.376(5) . ?
C2 H2 0.9500 . ?
C3 N2 1.387(4) . ?
C3 H3 0.9500 . ?
C4 N1 1.461(5) . ?
C4 C5 1.513(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 S1 1.823(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C8 1.518(6) . ?
C6 C7 1.523(5) . ?
C6 C9 1.523(6) . ?
C6 S1 1.855(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 N2 1.474(4) . ?
C10 C11 1.512(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.381(5) . ?
C11 C12 1.388(5) . ?
C12 C13 1.389(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C21 1.401(7) . ?
C17 C18 1.408(7) . ?
C17 Ni1 2.076(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(8) . ?
C18 Ni1 2.126(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.410(7) . ?
C19 Ni1 2.105(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.350(6) . ?
C20 Ni1 2.117(4) . ?
C20 H20 0.9500 . ?
C21 Ni1 2.147(4) . ?
C21 H21 0.9500 . ?
F1 P1 1.633(4) . ?
F2 P1 1.607(6) . ?
F3 P1 1.550(5) . ?
F4 P1 1.565(5) . ?
F1B P1 1.500(10) . ?
F2B P1 1.599(16) . ?
F3B P1 1.683(13) . ?
F4B P1 1.681(12) . ?
F5 P1 1.581(3) . ?
F6 P1 1.568(3) . ?
S1 Ni1 2.1815(10) . ?

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
N2 C1 N1 104.5(3) . . ?
N2 C1 Ni1 135.1(2) . . ?
N1 C1 Ni1 120.4(2) . . ?
C3 C2 N1 106.8(3) . . ?
C3 C2 H2 126.6 . . ?
N1 C2 H2 126.6 . . ?
C2 C3 N2 106.9(3) . . ?
C2 C3 H3 126.5 . . ?
N2 C3 H3 126.5 . . ?
N1 C4 C5 110.9(3) . . ?
N1 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 S1 111.9(3) . . ?
C4 C5 H5A 109.2 . . ?
S1 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
S1 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C8 C6 C7 111.1(4) . . ?
C8 C6 C9 110.7(4) . . ?
C7 C6 C9 111.4(4) . . ?
C8 C6 S1 111.7(3) . . ?
C7 C6 S1 107.2(3) . . ?
C9 C6 S1 104.6(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 111.6(3) . . ?
N2 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C16 C11 C12 119.2(3) . . ?
C16 C11 C10 120.8(3) . . ?
C12 C11 C10 120.0(3) . . ?
C11 C12 C13 120.3(4) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.7(4) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120.2(4) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 120.4(4) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C21 C17 C18 108.3(4) . . ?
C21 C17 Ni1 73.4(2) . . ?
C18 C17 Ni1 72.4(3) . . ?
C21 C17 H17 125.8 . . ?
C18 C17 H17 125.8 . . ?
Ni1 C17 H17 120.2 . . ?
C19 C18 C17 106.6(4) . . ?
C19 C18 Ni1 70.0(3) . . ?
C17 C18 Ni1 68.5(2) . . ?
C19 C18 H18 126.7 . . ?
C17 C18 H18 126.7 . . ?
Ni1 C18 H18 126.3 . . ?
C18 C19 C20 107.9(4) . . ?
C18 C19 Ni1 71.7(3) . . ?
C20 C19 Ni1 71.0(2) . . ?
C18 C19 H19 126.0 . . ?
C20 C19 H19 126.0 . . ?
Ni1 C19 H19 123.0 . . ?
C21 C20 C19 109.0(4) . . ?
C21 C20 Ni1 72.7(2) . . ?
C19 C20 Ni1 70.0(2) . . ?
C21 C20 H20 125.5 . . ?
C19 C20 H20 125.5 . . ?
Ni1 C20 H20 123.3 . . ?
C20 C21 C17 107.9(4) . . ?
C20 C21 Ni1 70.3(2) . . ?
C17 C21 Ni1 67.9(2) . . ?
C20 C21 H21 126.0 . . ?
C17 C21 H21 126.0 . . ?
Ni1 C21 H21 127.2 . . ?
C1 N1 C2 111.1(3) . . ?
C1 N1 C4 123.1(3) . . ?
C2 N1 C4 125.8(3) . . ?
C1 N2 C3 110.7(3) . . ?
C1 N2 C10 126.6(3) . . ?
C3 N2 C10 122.6(3) . . ?
F3 P1 F4 97.5(3) . . ?
F1B P1 F6 80.3(4) . . ?
F3 P1 F6 97.0(3) . . ?
F4 P1 F6 100.0(3) . . ?
F1B P1 F5 101.3(4) . . ?
F3 P1 F5 82.9(3) . . ?
F4 P1 F5 83.0(3) . . ?
F6 P1 F5 176.9(2) . . ?
F1B P1 F2B 98.6(6) . . ?
F6 P1 F2B 92.1(6) . . ?
F5 P1 F2B 85.2(6) . . ?
F3 P1 F2 88.5(3) . . ?
F4 P1 F2 170.5(3) . . ?
F6 P1 F2 86.5(3) . . ?
F5 P1 F2 90.4(3) . . ?
F3 P1 F1 169.8(3) . . ?
F4 P1 F1 86.9(3) . . ?
F6 P1 F1 91.3(2) . . ?
F5 P1 F1 88.6(2) . . ?
F2 P1 F1 86.0(3) . . ?
F1B P1 F4B 91.6(7) . . ?
F6 P1 F4B 78.6(5) . . ?
F5 P1 F4B 103.8(5) . . ?
F2B P1 F4B 164.9(7) . . ?
F1B P1 F3B 165.7(6) . . ?
F6 P1 F3B 85.6(5) . . ?
F5 P1 F3B 92.8(5) . . ?
F2B P1 F3B 84.3(7) . . ?
F4B P1 F3B 83.1(7) . . ?
C5 S1 C6 103.8(2) . . ?
C5 S1 Ni1 107.35(14) . . ?
C6 S1 Ni1 112.56(12) . . ?
C1 Ni1 C17 169.80(16) . . ?
C1 Ni1 C19 107.34(18) . . ?
C17 Ni1 C19 64.84(19) . . ?
C1 Ni1 C20 105.71(16) . . ?
C17 Ni1 C20 64.09(17) . . ?
C19 Ni1 C20 39.0(2) . . ?
C1 Ni1 C18 137.8(2) . . ?
C17 Ni1 C18 39.1(2) . . ?
C19 Ni1 C18 38.3(2) . . ?
C20 Ni1 C18 64.47(19) . . ?
C1 Ni1 C21 132.85(16) . . ?
C17 Ni1 C21 38.71(18) . . ?
C19 Ni1 C21 63.82(18) . . ?
C20 Ni1 C21 36.92(17) . . ?
C18 Ni1 C21 64.41(18) . . ?
C1 Ni1 S1 95.94(10) . . ?
C17 Ni1 S1 92.86(13) . . ?
C19 Ni1 S1 155.32(18) . . ?
C20 Ni1 S1 141.24(14) . . ?
C18 Ni1 S1 117.30(19) . . ?
C21 Ni1 S1 105.91(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 0.1(4) . . . . ?
N1 C4 C5 S1 65.8(4) . . . . ?
N2 C10 C11 C16 83.9(4) . . . . ?
N2 C10 C11 C12 -94.6(4) . . . . ?
C16 C11 C12 C13 -1.4(5) . . . . ?
C10 C11 C12 C13 177.1(3) . . . . ?
C11 C12 C13 C14 0.6(6) . . . . ?
C12 C13 C14 C15 0.7(6) . . . . ?
C13 C14 C15 C16 -1.1(6) . . . . ?
C12 C11 C16 C15 1.0(5) . . . . ?
C10 C11 C16 C15 -177.5(3) . . . . ?
C14 C15 C16 C11 0.3(6) . . . . ?
C21 C17 C18 C19 -5.1(5) . . . . ?
Ni1 C17 C18 C19 60.0(3) . . . . ?
C21 C17 C18 Ni1 -65.0(3) . . . . ?
C17 C18 C19 C20 3.1(5) . . . . ?
Ni1 C18 C19 C20 62.1(3) . . . . ?
C17 C18 C19 Ni1 -59.0(3) . . . . ?
C18 C19 C20 C21 0.1(5) . . . . ?
Ni1 C19 C20 C21 62.7(3) . . . . ?
C18 C19 C20 Ni1 -62.6(3) . . . . ?
C19 C20 C21 C17 -3.3(5) . . . . ?
Ni1 C20 C21 C17 57.7(3) . . . . ?
C19 C20 C21 Ni1 -61.0(3) . . . . ?
C18 C17 C21 C20 5.2(5) . . . . ?
Ni1 C17 C21 C20 -59.2(3) . . . . ?
C18 C17 C21 Ni1 64.4(3) . . . . ?
N2 C1 N1 C2 1.0(4) . . . . ?
Ni1 C1 N1 C2 -178.2(2) . . . . ?
N2 C1 N1 C4 -179.1(3) . . . . ?
Ni1 C1 N1 C4 1.7(4) . . . . ?
C3 C2 N1 C1 -0.7(4) . . . . ?
C3 C2 N1 C4 179.4(3) . . . . ?
C5 C4 N1 C1 -68.0(5) . . . . ?
C5 C4 N1 C2 111.9(4) . . . . ?
N1 C1 N2 C3 -0.9(4) . . . . ?
Ni1 C1 N2 C3 178.1(3) . . . . ?
N1 C1 N2 C10 -176.6(3) . . . . ?
Ni1 C1 N2 C10 2.5(5) . . . . ?
C2 C3 N2 C1 0.6(4) . . . . ?
C2 C3 N2 C10 176.4(3) . . . . ?
C11 C10 N2 C1 96.3(4) . . . . ?
C11 C10 N2 C3 -78.9(4) . . . . ?
C4 C5 S1 C6 -131.8(3) . . . . ?
C4 C5 S1 Ni1 -12.4(4) . . . . ?
C8 C6 S1 C5 56.9(3) . . . . ?
C7 C6 S1 C5 -65.0(3) . . . . ?
C9 C6 S1 C5 176.7(3) . . . . ?
C8 C6 S1 Ni1 -58.8(3) . . . . ?
C7 C6 S1 Ni1 179.3(2) . . . . ?
C9 C6 S1 Ni1 60.9(3) . . . . ?
N2 C1 Ni1 C17 74.3(11) . . . . ?
N1 C1 Ni1 C17 -106.8(10) . . . . ?
N2 C1 Ni1 C19 35.5(4) . . . . ?
N1 C1 Ni1 C19 -145.6(3) . . . . ?
N2 C1 Ni1 C20 76.3(4) . . . . ?
N1 C1 Ni1 C20 -104.8(3) . . . . ?
N2 C1 Ni1 C18 7.1(5) . . . . ?
N1 C1 Ni1 C18 -173.9(3) . . . . ?
N2 C1 Ni1 C21 105.6(4) . . . . ?
N1 C1 Ni1 C21 -75.5(3) . . . . ?
N2 C1 Ni1 S1 -136.2(3) . . . . ?
N1 C1 Ni1 S1 42.7(3) . . . . ?

_refine_diff_density_max         1.106
_refine_diff_density_min         -0.910
_refine_diff_density_rms         0.079

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: THF / n-pentane'
####################################################################### 
# 
# 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_mcfu170413
_database_code_depnum_ccdc_archive 'CCDC 1867502'
_audit_update_record             
;
2018-09-13 deposited with the CCDC.
2018-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H31 N2 Ni S, F6 P'
_chemical_formula_sum            'C23 H31 F6 N2 Ni P S'
_chemical_formula_weight         571.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.2564(3)
_cell_length_b                   15.4610(4)
_cell_length_c                   27.1428(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5143.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9912
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      29.97

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             2368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.956
_shelx_estimated_absorpt_T_min   0.796
_shelx_estimated_absorpt_T_max   0.847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6508
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50260
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.239
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7498
_reflns_number_gt                5579
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0298P)²+4.6493P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7498
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.31390(15) 0.86466(12) 0.62896(6) 0.0233(4) Uani 1 1 d . . . . .
C2 C 0.19253(18) 0.77621(14) 0.66621(8) 0.0332(5) Uani 1 1 d . . . . .
H2 H 0.1633 0.7337 0.6878 0.040 Uiso 1 1 calc R U . . .
C3 C 0.13676(17) 0.82400(14) 0.63352(8) 0.0329(5) Uani 1 1 d . . . . .
H3 H 0.0606 0.8213 0.6272 0.039 Uiso 1 1 calc R U . . .
C4 C 0.39328(18) 0.75863(13) 0.68665(7) 0.0311(4) Uani 1 1 d . . . . .
H4A H 0.4469 0.7410 0.6613 0.037 Uiso 1 1 calc R U . . .
H4B H 0.3672 0.7056 0.7034 0.037 Uiso 1 1 calc R U . . .
C5 C 0.4496(2) 0.81593(13) 0.72404(7) 0.0342(5) Uani 1 1 d . . . . .
H5A H 0.5137 0.7848 0.7375 0.041 Uiso 1 1 calc R U . . .
H5B H 0.3989 0.8271 0.7517 0.041 Uiso 1 1 calc R U . . .
C6 C 0.41851(16) 0.99726(13) 0.73773(7) 0.0270(4) Uani 1 1 d . . . . .
C7 C 0.29563(18) 0.98444(18) 0.73585(8) 0.0406(5) Uani 1 1 d . . . . .
H7A H 0.2771 0.9276 0.7495 0.061 Uiso 1 1 calc R U . . .
H7B H 0.2708 0.9878 0.7016 0.061 Uiso 1 1 calc R U . . .
H7C H 0.2598 1.0297 0.7553 0.061 Uiso 1 1 calc R U . . .
C8 C 0.4518(2) 1.08485(15) 0.71737(9) 0.0456(6) Uani 1 1 d . . . . .
H8A H 0.4217 1.1307 0.7383 0.068 Uiso 1 1 calc R U . . .
H8B H 0.4237 1.0912 0.6838 0.068 Uiso 1 1 calc R U . . .
H8C H 0.5316 1.0892 0.7169 0.068 Uiso 1 1 calc R U . . .
C9 C 0.4604(2) 0.98725(16) 0.79022(8) 0.0393(5) Uani 1 1 d . . . . .
H9A H 0.4289 1.0327 0.8110 0.059 Uiso 1 1 calc R U . . .
H9B H 0.5401 0.9922 0.7904 0.059 Uiso 1 1 calc R U . . .
H9C H 0.4391 0.9304 0.8030 0.059 Uiso 1 1 calc R U . . .
C10 C 0.18845(15) 0.92453(13) 0.56527(7) 0.0247(4) Uani 1 1 d . . . . .
C11 C 0.18756(17) 0.87656(15) 0.52183(7) 0.0315(4) Uani 1 1 d . . . . .
C12 C 0.16545(18) 0.91991(17) 0.47778(8) 0.0373(5) Uani 1 1 d . . . . .
H12 H 0.1656 0.8884 0.4477 0.045 Uiso 1 1 calc R U . . .
C13 C 0.14332(16) 1.00761(16) 0.47686(8) 0.0337(5) Uani 1 1 d . . . . .
C14 C 0.14464(16) 1.05271(15) 0.52088(8) 0.0326(4) Uani 1 1 d . . . . .
H14 H 0.1297 1.1130 0.5204 0.039 Uiso 1 1 calc R U . . .
C15 C 0.16709(16) 1.01299(13) 0.56582(7) 0.0278(4) Uani 1 1 d . . . . .
C16 C 0.2111(2) 0.78052(16) 0.52150(9) 0.0490(6) Uani 1 1 d . . . . .
H16A H 0.2726 0.7682 0.5435 0.074 Uiso 1 1 calc R U . . .
H16B H 0.2295 0.7622 0.4879 0.074 Uiso 1 1 calc R U . . .
H16C H 0.1465 0.7489 0.5329 0.074 Uiso 1 1 calc R U . . .
C17 C 0.11657(19) 1.0527(2) 0.42903(9) 0.0480(6) Uani 1 1 d . . . . .
H17A H 0.1363 1.0152 0.4013 0.072 Uiso 1 1 calc R U . . .
H17B H 0.1578 1.1069 0.4269 0.072 Uiso 1 1 calc R U . . .
H17C H 0.0382 1.0653 0.4278 0.072 Uiso 1 1 calc R U . . .
C18 C 0.1692(2) 1.06524(15) 0.61238(8) 0.0417(5) Uani 1 1 d . . . . .
H18A H 0.1298 1.0342 0.6383 0.063 Uiso 1 1 calc R U . . .
H18B H 0.1343 1.1213 0.6066 0.063 Uiso 1 1 calc R U . . .
H18C H 0.2450 1.0743 0.6226 0.063 Uiso 1 1 calc R U . . .
C19 C 0.4775(2) 0.9073(2) 0.54647(8) 0.0538(8) Uani 1 1 d . . . . .
H19 H 0.4387 0.8656 0.5277 0.065 Uiso 1 1 calc R U . . .
C20 C 0.4451(2) 0.9949(2) 0.55475(10) 0.0583(9) Uani 1 1 d . . . . .
H20 H 0.3823 1.0224 0.5415 0.070 Uiso 1 1 calc R U . . .
C21 C 0.5208(2) 1.03168(19) 0.58511(10) 0.0540(7) Uani 1 1 d . . . . .
H21 H 0.5208 1.0898 0.5965 0.065 Uiso 1 1 calc R U . . .
C22 C 0.5982(2) 0.9685(2) 0.59634(9) 0.0472(6) Uani 1 1 d . . . . .
H22 H 0.6575 0.9761 0.6185 0.057 Uiso 1 1 calc R U . . .
C23 C 0.5764(2) 0.89374(19) 0.57084(9) 0.0486(6) Uani 1 1 d . . . . .
H23 H 0.6199 0.8429 0.5700 0.058 Uiso 1 1 calc R U . . .
N1 N 0.30098(14) 0.80077(10) 0.66252(6) 0.0262(3) Uani 1 1 d . . . . .
N2 N 0.21193(13) 0.87841(11) 0.61057(6) 0.0242(3) Uani 1 1 d . . . . .
F1 F 0.75117(18) 0.82299(10) 0.66606(7) 0.0756(6) Uani 1 1 d . . . . .
F2 F 0.63785(13) 0.70895(15) 0.65464(9) 0.0862(6) Uani 1 1 d . . . . .
F3 F 0.77950(16) 0.62069(10) 0.65566(7) 0.0676(5) Uani 1 1 d . . . . .
F4 F 0.89279(12) 0.73454(12) 0.66714(7) 0.0645(5) Uani 1 1 d . . . . .
F5 F 0.75309(17) 0.71190(13) 0.71857(5) 0.0724(5) Uani 1 1 d . . . . .
F6 F 0.77757(18) 0.73212(13) 0.60299(6) 0.0757(6) Uani 1 1 d . . . . .
P1 P 0.76499(5) 0.72189(4) 0.66042(2) 0.03014(12) Uani 1 1 d . . . . .
S1 S 0.49447(4) 0.91872(3) 0.69876(2) 0.02459(10) Uani 1 1 d . . . . .
Ni1 Ni 0.44726(2) 0.92181(2) 0.62064(2) 0.02341(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.353(2) . ?
C1 N2 1.362(2) . ?
C1 Ni1 1.8717(19) . ?
C2 C3 1.342(3) . ?
C2 N1 1.386(3) . ?
C2 H2 0.9500 . ?
C3 N2 1.394(2) . ?
C3 H3 0.9500 . ?
C4 N1 1.461(3) . ?
C4 C5 1.514(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 S1 1.816(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C8 1.519(3) . ?
C6 C7 1.520(3) . ?
C6 C9 1.522(3) . ?
C6 S1 1.860(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.393(3) . ?
C10 C11 1.393(3) . ?
C10 N2 1.450(2) . ?
C11 C12 1.397(3) . ?
C11 C16 1.513(3) . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(3) . ?
C13 C17 1.510(3) . ?
C14 C15 1.393(3) . ?
C14 H14 0.9500 . ?
C15 C18 1.500(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C23 1.397(4) . ?
C19 C20 1.429(4) . ?
C19 Ni1 2.059(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.366(4) . ?
C20 Ni1 2.116(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.395(4) . ?
C21 Ni1 2.151(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.373(4) . ?
C22 Ni1 2.093(2) . ?
C22 H22 0.9500 . ?
C23 Ni1 2.126(2) . ?
C23 H23 0.9500 . ?
F1 P1 1.5798(16) . ?
F2 P1 1.5788(17) . ?
F3 P1 1.5799(16) . ?
F4 P1 1.5892(16) . ?
F5 P1 1.5926(16) . ?
F6 P1 1.5744(16) . ?
S1 Ni1 2.1984(5) . ?

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
N1 C1 N2 104.67(16) . . ?
N1 C1 Ni1 121.87(14) . . ?
N2 C1 Ni1 133.09(14) . . ?
C3 C2 N1 106.85(18) . . ?
C3 C2 H2 126.6 . . ?
N1 C2 H2 126.6 . . ?
C2 C3 N2 106.92(18) . . ?
C2 C3 H3 126.5 . . ?
N2 C3 H3 126.5 . . ?
N1 C4 C5 113.13(17) . . ?
N1 C4 H4A 109.0 . . ?
C5 C4 H4A 109.0 . . ?
N1 C4 H4B 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C4 C5 S1 113.38(14) . . ?
C4 C5 H5A 108.9 . . ?
S1 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
S1 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C8 C6 C7 111.7(2) . . ?
C8 C6 C9 109.91(19) . . ?
C7 C6 C9 110.62(18) . . ?
C8 C6 S1 103.92(14) . . ?
C7 C6 S1 113.06(15) . . ?
C9 C6 S1 107.29(14) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 122.04(18) . . ?
C15 C10 N2 120.75(17) . . ?
C11 C10 N2 117.21(18) . . ?
C10 C11 C12 118.1(2) . . ?
C10 C11 C16 121.75(19) . . ?
C12 C11 C16 120.2(2) . . ?
C13 C12 C11 121.6(2) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 118.4(2) . . ?
C12 C13 C17 120.7(2) . . ?
C14 C13 C17 120.8(2) . . ?
C13 C14 C15 122.4(2) . . ?
C13 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C10 C15 C14 117.43(19) . . ?
C10 C15 C18 122.32(19) . . ?
C14 C15 C18 120.2(2) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C23 C19 C20 108.0(2) . . ?
C23 C19 Ni1 73.12(13) . . ?
C20 C19 Ni1 72.12(14) . . ?
C23 C19 H19 126.0 . . ?
C20 C19 H19 126.0 . . ?
Ni1 C19 H19 120.6 . . ?
C21 C20 C19 107.5(2) . . ?
C21 C20 Ni1 72.76(15) . . ?
C19 C20 Ni1 67.88(13) . . ?
C21 C20 H20 126.3 . . ?
C19 C20 H20 126.3 . . ?
Ni1 C20 H20 124.7 . . ?
C20 C21 C22 107.6(3) . . ?
C20 C21 Ni1 69.91(15) . . ?
C22 C21 Ni1 68.54(14) . . ?
C20 C21 H21 126.2 . . ?
C22 C21 H21 126.2 . . ?
Ni1 C21 H21 126.9 . . ?
C23 C22 C21 110.3(2) . . ?
C23 C22 Ni1 72.34(14) . . ?
C21 C22 Ni1 73.10(15) . . ?
C23 C22 H22 124.8 . . ?
C21 C22 H22 124.8 . . ?
Ni1 C22 H22 121.3 . . ?
C22 C23 C19 106.3(3) . . ?
C22 C23 Ni1 69.68(14) . . ?
C19 C23 Ni1 67.94(13) . . ?
C22 C23 H23 126.8 . . ?
C19 C23 H23 126.8 . . ?
Ni1 C23 H23 127.1 . . ?
C1 N1 C2 111.16(17) . . ?
C1 N1 C4 122.48(17) . . ?
C2 N1 C4 126.02(17) . . ?
C1 N2 C3 110.38(17) . . ?
C1 N2 C10 124.71(15) . . ?
C3 N2 C10 122.98(16) . . ?
F6 P1 F2 90.63(12) . . ?
F6 P1 F1 90.40(11) . . ?
F2 P1 F1 91.67(12) . . ?
F6 P1 F3 90.43(10) . . ?
F2 P1 F3 88.71(11) . . ?
F1 P1 F3 179.08(11) . . ?
F6 P1 F4 90.27(10) . . ?
F2 P1 F4 179.09(12) . . ?
F1 P1 F4 88.44(11) . . ?
F3 P1 F4 91.16(10) . . ?
F6 P1 F5 179.57(12) . . ?
F2 P1 F5 89.76(11) . . ?
F1 P1 F5 89.43(11) . . ?
F3 P1 F5 89.73(10) . . ?
F4 P1 F5 89.33(10) . . ?
C5 S1 C6 101.82(10) . . ?
C5 S1 Ni1 107.68(7) . . ?
C6 S1 Ni1 113.74(6) . . ?
C1 Ni1 C19 102.94(9) . . ?
C1 Ni1 C22 166.63(9) . . ?
C19 Ni1 C22 64.53(10) . . ?
C1 Ni1 C20 110.06(10) . . ?
C19 Ni1 C20 40.00(12) . . ?
C22 Ni1 C20 63.94(10) . . ?
C1 Ni1 C23 129.08(10) . . ?
C19 Ni1 C23 38.94(11) . . ?
C22 Ni1 C23 37.98(11) . . ?
C20 Ni1 C23 65.23(10) . . ?
C1 Ni1 C21 142.45(11) . . ?
C19 Ni1 C21 64.67(11) . . ?
C22 Ni1 C21 38.36(11) . . ?
C20 Ni1 C21 37.33(12) . . ?
C23 Ni1 C21 64.16(11) . . ?
C1 Ni1 S1 95.93(6) . . ?
C19 Ni1 S1 153.26(9) . . ?
C22 Ni1 S1 94.52(7) . . ?
C20 Ni1 S1 146.14(10) . . ?
C23 Ni1 S1 114.38(8) . . ?
C21 Ni1 S1 109.83(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 -0.8(2) . . . . ?
N1 C4 C5 S1 -55.2(2) . . . . ?
C15 C10 C11 C12 0.7(3) . . . . ?
N2 C10 C11 C12 -179.79(18) . . . . ?
C15 C10 C11 C16 179.8(2) . . . . ?
N2 C10 C11 C16 -0.6(3) . . . . ?
C10 C11 C12 C13 -1.0(3) . . . . ?
C16 C11 C12 C13 179.8(2) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C11 C12 C13 C17 -178.3(2) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C17 C13 C14 C15 178.86(19) . . . . ?
C11 C10 C15 C14 -0.1(3) . . . . ?
N2 C10 C15 C14 -179.66(17) . . . . ?
C11 C10 C15 C18 -179.2(2) . . . . ?
N2 C10 C15 C18 1.2(3) . . . . ?
C13 C14 C15 C10 -0.1(3) . . . . ?
C13 C14 C15 C18 179.0(2) . . . . ?
C23 C19 C20 C21 -2.4(3) . . . . ?
Ni1 C19 C20 C21 62.40(17) . . . . ?
C23 C19 C20 Ni1 -64.80(16) . . . . ?
C19 C20 C21 C22 -0.9(3) . . . . ?
Ni1 C20 C21 C22 58.36(17) . . . . ?
C19 C20 C21 Ni1 -59.27(16) . . . . ?
C20 C21 C22 C23 4.0(3) . . . . ?
Ni1 C21 C22 C23 63.22(17) . . . . ?
C20 C21 C22 Ni1 -59.22(17) . . . . ?
C21 C22 C23 C19 -5.4(3) . . . . ?
Ni1 C22 C23 C19 58.27(16) . . . . ?
C21 C22 C23 Ni1 -63.70(17) . . . . ?
C20 C19 C23 C22 4.7(3) . . . . ?
Ni1 C19 C23 C22 -59.39(17) . . . . ?
C20 C19 C23 Ni1 64.14(16) . . . . ?
N2 C1 N1 C2 -1.6(2) . . . . ?
Ni1 C1 N1 C2 172.36(14) . . . . ?
N2 C1 N1 C4 172.12(16) . . . . ?
Ni1 C1 N1 C4 -14.0(2) . . . . ?
C3 C2 N1 C1 1.5(2) . . . . ?
C3 C2 N1 C4 -171.88(18) . . . . ?
C5 C4 N1 C1 72.0(2) . . . . ?
C5 C4 N1 C2 -115.3(2) . . . . ?
N1 C1 N2 C3 1.0(2) . . . . ?
Ni1 C1 N2 C3 -171.90(15) . . . . ?
N1 C1 N2 C10 -163.48(17) . . . . ?
Ni1 C1 N2 C10 23.6(3) . . . . ?
C2 C3 N2 C1 -0.1(2) . . . . ?
C2 C3 N2 C10 164.69(18) . . . . ?
C15 C10 N2 C1 -92.5(2) . . . . ?
C11 C10 N2 C1 88.0(2) . . . . ?
C15 C10 N2 C3 104.9(2) . . . . ?
C11 C10 N2 C3 -74.7(2) . . . . ?
C4 C5 S1 C6 120.33(17) . . . . ?
C4 C5 S1 Ni1 0.44(19) . . . . ?
C8 C6 S1 C5 -179.04(15) . . . . ?
C7 C6 S1 C5 -57.68(18) . . . . ?
C9 C6 S1 C5 64.56(17) . . . . ?
C8 C6 S1 Ni1 -63.51(16) . . . . ?
C7 C6 S1 Ni1 57.86(17) . . . . ?
C9 C6 S1 Ni1 -179.91(13) . . . . ?
N1 C1 Ni1 C19 125.58(17) . . . . ?
N2 C1 Ni1 C19 -62.5(2) . . . . ?
N1 C1 Ni1 C22 105.9(4) . . . . ?
N2 C1 Ni1 C22 -82.2(5) . . . . ?
N1 C1 Ni1 C20 166.74(17) . . . . ?
N2 C1 Ni1 C20 -21.3(2) . . . . ?
N1 C1 Ni1 C23 92.89(18) . . . . ?
N2 C1 Ni1 C23 -95.2(2) . . . . ?
N1 C1 Ni1 C21 -169.34(16) . . . . ?
N2 C1 Ni1 C21 2.6(3) . . . . ?
N1 C1 Ni1 S1 -35.34(15) . . . . ?
N2 C1 Ni1 S1 136.59(18) . . . . ?

_refine_diff_density_max         0.481
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.062

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/n-pentane'
_chemical_properties_physical    Air-sensitive
####################################################################### 
# 
# 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_mcfu160617
_database_code_depnum_ccdc_archive 'CCDC 1867501'
_audit_update_record             
;
2018-09-13 deposited with the CCDC.
2018-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H23 Br N2 Ni S'
_chemical_formula_sum            'C23 H23 Br N2 Ni S'
_chemical_formula_weight         498.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.561(4)
_cell_length_b                   15.486(6)
_cell_length_c                   16.237(5)
_cell_angle_alpha                90
_cell_angle_beta                 113.976(17)
_cell_angle_gamma                90
_cell_volume                     2196.6(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9428
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      29.53

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.808
_shelx_estimated_absorpt_T_min   0.365
_shelx_estimated_absorpt_T_max   0.604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5732
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30977
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.901
_diffrn_reflns_theta_max         30.308
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             6301
_reflns_number_gt                4277
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0369P)²+2.5910P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6301
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0454(3) 0.88997(17) 0.86375(18) 0.0392(6) Uani 1 1 d . . . . .
C2 C -0.0930(4) 1.01267(19) 0.8252(2) 0.0512(7) Uani 1 1 d . . . . .
H2 H -0.1756 1.0521 0.8113 0.061 Uiso 1 1 calc R U . . .
C3 C 0.0456(4) 1.02991(18) 0.8280(2) 0.0518(7) Uani 1 1 d . . . . .
H3 H 0.0802 1.0841 0.8162 0.062 Uiso 1 1 calc R U . . .
C4 C -0.2174(3) 0.8834(2) 0.8599(2) 0.0500(7) Uani 1 1 d . . . . .
H4A H -0.2109 0.8203 0.8526 0.060 Uiso 1 1 calc R U . . .
H4B H -0.3167 0.9038 0.8141 0.060 Uiso 1 1 calc R U . . .
C5 C -0.2081(4) 0.9028(2) 0.9525(2) 0.0559(8) Uani 1 1 d . . . . .
H5A H -0.2117 0.9661 0.9597 0.067 Uiso 1 1 calc R U . . .
H5B H -0.1086 0.8819 0.9976 0.067 Uiso 1 1 calc R U . . .
C6 C -0.2902(3) 0.7526(2) 1.0238(2) 0.0503(7) Uani 1 1 d . . . . .
C7 C -0.1574(4) 0.7142(2) 1.0272(2) 0.0620(9) Uani 1 1 d . . . . .
H7 H -0.0960 0.7426 1.0019 0.074 Uiso 1 1 calc R U . . .
C8 C -0.1146(5) 0.6343(3) 1.0676(3) 0.0779(12) Uani 1 1 d . . . . .
H8 H -0.0236 0.6078 1.0698 0.093 Uiso 1 1 calc R U . . .
C9 C -0.2006(6) 0.5933(3) 1.1041(3) 0.0866(14) Uani 1 1 d . . . . .
H9 H -0.1701 0.5384 1.1317 0.104 Uiso 1 1 calc R U . . .
C10 C -0.3320(6) 0.6313(3) 1.1013(3) 0.0857(13) Uani 1 1 d . . . . .
H10 H -0.3920 0.6026 1.1273 0.103 Uiso 1 1 calc R U . . .
C11 C -0.3779(4) 0.7106(3) 1.0610(3) 0.0680(9) Uani 1 1 d . . . . .
H11 H -0.4696 0.7363 1.0588 0.082 Uiso 1 1 calc R U . . .
C12 C 0.2928(3) 0.9473(2) 0.8697(2) 0.0538(7) Uani 1 1 d . . . . .
H12A H 0.3225 0.8857 0.8784 0.065 Uiso 1 1 calc R U . . .
H12B H 0.3536 0.9780 0.9265 0.065 Uiso 1 1 calc R U . . .
C13 C 0.3315(3) 0.9832(2) 0.7962(2) 0.0518(7) Uani 1 1 d . . . . .
C14 C 0.4168(4) 1.0568(2) 0.8094(3) 0.0637(9) Uani 1 1 d . . . . .
H14 H 0.4502 1.0861 0.8655 0.076 Uiso 1 1 calc R U . . .
C15 C 0.4549(5) 1.0889(3) 0.7423(3) 0.0819(12) Uani 1 1 d . . . . .
H15 H 0.5157 1.1395 0.7527 0.098 Uiso 1 1 calc R U . . .
C16 C 0.4062(5) 1.0487(4) 0.6617(3) 0.0981(17) Uani 1 1 d . . . . .
H16 H 0.4288 1.0722 0.6144 0.118 Uiso 1 1 calc R U . . .
C17 C 0.3247(6) 0.9745(5) 0.6488(3) 0.116(2) Uani 1 1 d . . . . .
H17 H 0.2932 0.9450 0.5929 0.139 Uiso 1 1 calc R U . . .
C18 C 0.2874(5) 0.9418(3) 0.7152(3) 0.0894(14) Uani 1 1 d . . . . .
H18 H 0.2302 0.8898 0.7050 0.107 Uiso 1 1 calc R U . . .
C19 C -0.0314(6) 0.6720(3) 0.8347(5) 0.0951(17) Uani 1 1 d . . . . .
H19 H -0.1327 0.6624 0.8298 0.114 Uiso 1 1 calc R U . . .
C20 C 0.0924(10) 0.6409(2) 0.8954(3) 0.103(2) Uani 1 1 d . . . . .
H20 H 0.0968 0.6076 0.9455 0.124 Uiso 1 1 calc R U . . .
C21 C 0.2142(6) 0.6618(4) 0.8784(6) 0.126(3) Uani 1 1 d . . . . .
H21 H 0.3170 0.6450 0.9133 0.151 Uiso 1 1 calc R U . . .
C22 C 0.1662(12) 0.7103(4) 0.8042(6) 0.142(3) Uani 1 1 d . . . . .
H22 H 0.2261 0.7327 0.7746 0.170 Uiso 1 1 calc R U . . .
C23 C 0.0097(10) 0.7210(3) 0.7792(3) 0.117(3) Uani 1 1 d . . . . .
H23 H -0.0565 0.7564 0.7315 0.140 Uiso 1 1 calc R U . . .
N1 N -0.0928(3) 0.92620(14) 0.84635(16) 0.0425(5) Uani 1 1 d . . . . .
N2 N 0.1290(3) 0.95485(14) 0.85126(16) 0.0445(5) Uani 1 1 d . . . . .
S1 S -0.36037(10) 0.85367(7) 0.97466(7) 0.0685(3) Uani 1 1 d . . . . .
Ni1 Ni 0.11071(4) 0.77726(2) 0.89928(2) 0.04201(10) Uani 1 1 d . . . . .
Br1 Br 0.23112(4) 0.80913(2) 1.05104(2) 0.06357(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.349(4) . ?
C1 N1 1.356(3) . ?
C1 Ni1 1.864(3) . ?
C2 C3 1.334(5) . ?
C2 N1 1.382(4) . ?
C2 H2 0.9500 . ?
C3 N2 1.373(4) . ?
C3 H3 0.9500 . ?
C4 N1 1.455(4) . ?
C4 C5 1.500(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 S1 1.804(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C11 1.378(5) . ?
C6 C7 1.383(5) . ?
C6 S1 1.761(3) . ?
C7 C8 1.383(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.351(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.370(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(6) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 N2 1.475(4) . ?
C12 C13 1.492(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.367(5) . ?
C13 C18 1.368(5) . ?
C14 C15 1.374(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.349(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.356(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.363(7) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.287(7) . ?
C19 C23 1.353(9) . ?
C19 Ni1 2.109(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.342(9) . ?
C20 Ni1 2.118(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.333(10) . ?
C21 Ni1 2.136(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.392(10) . ?
C22 Ni1 2.100(4) . ?
C22 H22 0.9500 . ?
C23 Ni1 1.992(4) . ?
C23 H23 0.9500 . ?
Ni1 Br1 2.3099(9) . ?

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
N2 C1 N1 104.3(2) . . ?
N2 C1 Ni1 126.8(2) . . ?
N1 C1 Ni1 128.8(2) . . ?
C3 C2 N1 106.5(3) . . ?
C3 C2 H2 126.7 . . ?
N1 C2 H2 126.7 . . ?
C2 C3 N2 107.3(3) . . ?
C2 C3 H3 126.3 . . ?
N2 C3 H3 126.3 . . ?
N1 C4 C5 110.0(3) . . ?
N1 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
N1 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C4 C5 S1 113.1(2) . . ?
C4 C5 H5A 109.0 . . ?
S1 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
S1 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C11 C6 C7 119.4(3) . . ?
C11 C6 S1 115.5(3) . . ?
C7 C6 S1 125.1(3) . . ?
C8 C7 C6 119.6(4) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C9 C8 C7 120.9(4) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 119.8(4) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C11 120.6(4) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C6 119.7(4) . . ?
C10 C11 H11 120.1 . . ?
C6 C11 H11 120.1 . . ?
N2 C12 C13 113.4(2) . . ?
N2 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
N2 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C18 118.1(4) . . ?
C14 C13 C12 120.8(3) . . ?
C18 C13 C12 121.0(3) . . ?
C13 C14 C15 120.7(4) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 120.3(4) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.3(4) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 120.8(5) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C13 120.6(4) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C20 C19 C23 107.1(5) . . ?
C20 C19 Ni1 72.7(3) . . ?
C23 C19 Ni1 66.1(3) . . ?
C20 C19 H19 126.4 . . ?
C23 C19 H19 126.4 . . ?
Ni1 C19 H19 126.3 . . ?
C19 C20 C21 110.9(6) . . ?
C19 C20 Ni1 71.9(3) . . ?
C21 C20 Ni1 72.3(3) . . ?
C19 C20 H20 124.5 . . ?
C21 C20 H20 124.5 . . ?
Ni1 C20 H20 122.8 . . ?
C22 C21 C20 108.2(6) . . ?
C22 C21 Ni1 70.2(3) . . ?
C20 C21 Ni1 70.9(3) . . ?
C22 C21 H21 125.9 . . ?
C20 C21 H21 125.9 . . ?
Ni1 C21 H21 124.6 . . ?
C21 C22 C23 105.4(5) . . ?
C21 C22 Ni1 73.1(3) . . ?
C23 C22 Ni1 66.0(3) . . ?
C21 C22 H22 127.3 . . ?
C23 C22 H22 127.3 . . ?
Ni1 C22 H22 125.1 . . ?
C19 C23 C22 108.0(5) . . ?
C19 C23 Ni1 75.5(3) . . ?
C22 C23 Ni1 74.4(3) . . ?
C19 C23 H23 126.0 . . ?
C22 C23 H23 126.0 . . ?
Ni1 C23 H23 116.2 . . ?
C1 N1 C2 110.8(3) . . ?
C1 N1 C4 124.7(2) . . ?
C2 N1 C4 124.1(2) . . ?
C1 N2 C3 111.0(2) . . ?
C1 N2 C12 123.8(2) . . ?
C3 N2 C12 124.9(3) . . ?
C6 S1 C5 106.00(16) . . ?
C1 Ni1 C23 97.97(15) . . ?
C1 Ni1 C22 112.8(3) . . ?
C23 Ni1 C22 39.7(3) . . ?
C1 Ni1 C19 120.2(2) . . ?
C23 Ni1 C19 38.4(3) . . ?
C22 Ni1 C19 63.7(2) . . ?
C1 Ni1 C20 155.6(2) . . ?
C23 Ni1 C20 62.2(2) . . ?
C22 Ni1 C20 61.8(2) . . ?
C19 Ni1 C20 35.5(2) . . ?
C1 Ni1 C21 148.5(3) . . ?
C23 Ni1 C21 63.2(2) . . ?
C22 Ni1 C21 36.7(3) . . ?
C19 Ni1 C21 61.4(2) . . ?
C20 Ni1 C21 36.8(3) . . ?
C1 Ni1 Br1 95.11(8) . . ?
C23 Ni1 Br1 166.27(16) . . ?
C22 Ni1 Br1 136.5(3) . . ?
C19 Ni1 Br1 129.6(2) . . ?
C20 Ni1 Br1 104.13(14) . . ?
C21 Ni1 Br1 106.6(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 -0.4(4) . . . . ?
N1 C4 C5 S1 179.0(2) . . . . ?
C11 C6 C7 C8 0.1(5) . . . . ?
S1 C6 C7 C8 -179.8(3) . . . . ?
C6 C7 C8 C9 -0.2(6) . . . . ?
C7 C8 C9 C10 0.0(7) . . . . ?
C8 C9 C10 C11 0.4(7) . . . . ?
C9 C10 C11 C6 -0.5(6) . . . . ?
C7 C6 C11 C10 0.3(6) . . . . ?
S1 C6 C11 C10 -179.8(3) . . . . ?
N2 C12 C13 C14 110.8(3) . . . . ?
N2 C12 C13 C18 -71.5(4) . . . . ?
C18 C13 C14 C15 1.0(6) . . . . ?
C12 C13 C14 C15 178.8(3) . . . . ?
C13 C14 C15 C16 1.1(7) . . . . ?
C14 C15 C16 C17 -2.7(8) . . . . ?
C15 C16 C17 C18 2.1(9) . . . . ?
C16 C17 C18 C13 0.0(9) . . . . ?
C14 C13 C18 C17 -1.5(7) . . . . ?
C12 C13 C18 C17 -179.3(4) . . . . ?
C23 C19 C20 C21 -4.8(5) . . . . ?
Ni1 C19 C20 C21 -62.2(4) . . . . ?
C23 C19 C20 Ni1 57.3(3) . . . . ?
C19 C20 C21 C22 1.3(6) . . . . ?
Ni1 C20 C21 C22 -60.5(3) . . . . ?
C19 C20 C21 Ni1 61.9(3) . . . . ?
C20 C21 C22 C23 2.6(5) . . . . ?
Ni1 C21 C22 C23 -58.3(3) . . . . ?
C20 C21 C22 Ni1 61.0(4) . . . . ?
C20 C19 C23 C22 6.4(5) . . . . ?
Ni1 C19 C23 C22 67.9(3) . . . . ?
C20 C19 C23 Ni1 -61.5(3) . . . . ?
C21 C22 C23 C19 -5.5(5) . . . . ?
Ni1 C22 C23 C19 -68.6(3) . . . . ?
C21 C22 C23 Ni1 63.1(4) . . . . ?
N2 C1 N1 C2 -1.2(3) . . . . ?
Ni1 C1 N1 C2 177.7(2) . . . . ?
N2 C1 N1 C4 -173.4(3) . . . . ?
Ni1 C1 N1 C4 5.4(4) . . . . ?
C3 C2 N1 C1 1.0(3) . . . . ?
C3 C2 N1 C4 173.3(3) . . . . ?
C5 C4 N1 C1 91.8(3) . . . . ?
C5 C4 N1 C2 -79.5(3) . . . . ?
N1 C1 N2 C3 0.9(3) . . . . ?
Ni1 C1 N2 C3 -178.0(2) . . . . ?
N1 C1 N2 C12 175.0(3) . . . . ?
Ni1 C1 N2 C12 -3.9(4) . . . . ?
C2 C3 N2 C1 -0.3(4) . . . . ?
C2 C3 N2 C12 -174.3(3) . . . . ?
C13 C12 N2 C1 134.1(3) . . . . ?
C13 C12 N2 C3 -52.6(4) . . . . ?
C11 C6 S1 C5 168.8(3) . . . . ?
C7 C6 S1 C5 -11.2(3) . . . . ?
C4 C5 S1 C6 91.7(3) . . . . ?
N2 C1 Ni1 C23 -102.9(4) . . . . ?
N1 C1 Ni1 C23 78.5(4) . . . . ?
N2 C1 Ni1 C22 -64.6(4) . . . . ?
N1 C1 Ni1 C22 116.9(4) . . . . ?
N2 C1 Ni1 C19 -136.4(3) . . . . ?
N1 C1 Ni1 C19 45.0(3) . . . . ?
N2 C1 Ni1 C20 -136.4(5) . . . . ?
N1 C1 Ni1 C20 45.0(6) . . . . ?
N2 C1 Ni1 C21 -52.8(4) . . . . ?
N1 C1 Ni1 C21 128.6(4) . . . . ?
N2 C1 Ni1 Br1 81.3(2) . . . . ?
N1 C1 Ni1 Br1 -97.3(2) . . . . ?

_refine_diff_density_max         0.588
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.065

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: thf / n-hexane'
