# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_K0960_0m_4_a
_database_code_depnum_ccdc_archive 'CCDC 2195892'
loop_
_audit_author_name
_audit_author_address
'Somayeh Norouziyanlakvan'
;University of Ottawa
Canada
;
_audit_update_record             
;
2022-08-09 deposited with the CCDC.	2022-11-07 downloaded from the CCDC.
;
#===============================================================================
# 5. CHEMICAL DATA

_chemical_name_systematic        
; 
;

_chemical_formula_sum            'C21 H19 Br2 N3 Ni'
_chemical_formula_moiety         ?
_chemical_formula_weight         531.92
#=============================================================
# 6. CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   15.9809(5)
_cell_length_b                   8.5994(3)
_cell_length_c                   15.5441(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.9980(10)
_cell_angle_gamma                90
_cell_volume                     2081.43(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    7181
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      30.50

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_min          0.21
_exptl_crystal_size_mid          0.252
_exptl_crystal_size_max          0.409

_exptl_crystal_density_diffrn    1.697
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    4.782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.582612
_exptl_absorpt_correction_T_max  0.745209
_exptl_absorpt_process_details   SADABS

#=============================================================================
# 7. EXPERIMENTAL DATA

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       'ω and φ scans'
_diffrn_ambient_temperature      203(2)
_diffrn_reflns_number            1913
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.616
_diffrn_reflns_theta_max         25.390
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999


#==========================================================================
# 8. REFINEMENT DATA

_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.
;

_reflns_number_total             1913
_reflns_number_gt                1747
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_special_details          none

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details none
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         1913
_refine_ls_number_parameters     126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0650
_refine_ls_wR_factor_gt          0.0616
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0309P)²+3.2499P] where P=(Fo²+2Fc²)/3'

#---------------------------------------------------------


#========================================================== 
# 9. General computing 

_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_cell_refinement       'Bruker SAINT'
_computing_structure_solution    
; 
 SHELXT 2014/5 (Sheldrick, 2014)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_shelx_SHELXL_version_number     2018/3

#===================================================================
# 10.  ATOMIC COORDINATES AND THERMAL PARAMETERS

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================
# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

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
Br1 Br 0.61529(2) 0.74239(4) 0.36020(2) 0.03857(11) Uani 1 1 d . . . . .
Ni1 Ni 0.500000 0.63613(5) 0.250000 0.02412(13) Uani 1 2 d S T P . .
N1 N 0.500000 0.4097(3) 0.250000 0.0255(6) Uani 1 2 d S T P . .
N2 N 0.41830(15) 0.5853(3) 0.33606(16) 0.0270(5) Uani 1 1 d . . . . .
C1 C 0.500000 0.0941(5) 0.250000 0.0537(13) Uani 1 2 d S T P . .
H1 H 0.500000 -0.015242 0.250000 0.064 Uiso 1 2 calc R U P . .
C2 C 0.4508(3) 0.1733(4) 0.2982(3) 0.0450(8) Uani 1 1 d . . . . .
H2 H 0.417076 0.119345 0.330689 0.054 Uiso 1 1 calc R U . . .
C3 C 0.4526(2) 0.3347(3) 0.2976(3) 0.0290(6) Uani 1 1 d . . . . .
C4 C 0.40491(19) 0.4404(3) 0.3455(2) 0.0290(6) Uani 1 1 d . . . . .
C5 C 0.3472(2) 0.3738(4) 0.3992(3) 0.0455(8) Uani 1 1 d . . . . .
H5A H 0.373230 0.281059 0.429347 0.068 Uiso 1 1 calc R U . . .
H5B H 0.292340 0.347138 0.360824 0.068 Uiso 1 1 calc R U . . .
H5C H 0.338329 0.449803 0.442423 0.068 Uiso 1 1 calc R U . . .
C6 C 0.3756(2) 0.7021(3) 0.3765(2) 0.0298(6) Uani 1 1 d . . . . .
C7 C 0.2916(3) 0.7401(5) 0.3412(3) 0.0553(14) Uani 1 1 d . . . . .
H7 H 0.259785 0.684265 0.292801 0.066 Uiso 1 1 calc R U . . .
C8 C 0.2540(3) 0.8612(6) 0.3774(3) 0.0617(12) Uani 1 1 d . . . . .
H8 H 0.196540 0.887680 0.352784 0.074 Uiso 1 1 calc R U . . .
C9 C 0.2990(3) 0.9430(4) 0.4484(3) 0.0471(8) Uani 1 1 d . . . . .
H9 H 0.272675 1.024724 0.472678 0.057 Uiso 1 1 calc R U . . .
C10 C 0.3824(3) 0.9043(5) 0.4835(3) 0.0525(10) Uani 1 1 d . . . . .
H10 H 0.413697 0.959273 0.532521 0.063 Uiso 1 1 calc R U . . .
C11 C 0.4216(3) 0.7844(5) 0.4473(3) 0.0462(9) Uani 1 1 d . . . . .
H11 H 0.479405 0.759540 0.471158 0.055 Uiso 1 1 calc R U . . .


_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
Br1 Ni1 2.3967(3) . ?
Ni1 N1 1.947(3) . ?
Ni1 N2 2.114(2) . ?
Ni1 N2 2.114(2) 2_655 ?
N1 C3 1.338(3) . ?
N1 C3 1.338(3) 2_655 ?
N2 C4 1.278(4) . ?
N2 C6 1.436(3) . ?
C1 C2 1.382(4) 2_655 ?
C1 C2 1.382(4) . ?
C1 H1 0.9400 . ?
C2 C3 1.388(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.489(4) . ?
C4 C5 1.491(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C6 C7 1.370(6) . ?
C6 C11 1.374(6) . ?
C7 C8 1.383(5) . ?
C7 H7 0.9400 . ?
C8 C9 1.369(6) . ?
C8 H8 0.9400 . ?
C9 C10 1.363(6) . ?
C9 H9 0.9400 . ?
C10 C11 1.390(5) . ?
C10 H10 0.9400 . ?
C11 H11 0.9400 . ?

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 Ni1 N2 78.07(6) . . ?
N1 Ni1 N2 78.07(6) . 2_655 ?
N2 Ni1 N2 156.15(12) . 2_655 ?
N1 Ni1 Br1 112.412(13) . . ?
N2 Ni1 Br1 96.40(7) . . ?
N2 Ni1 Br1 92.64(7) 2_655 . ?
N1 Ni1 Br1 112.411(13) . 2_655 ?
N2 Ni1 Br1 92.64(7) . 2_655 ?
N2 Ni1 Br1 96.40(7) 2_655 2_655 ?
Br1 Ni1 Br1 135.18(3) . 2_655 ?
C3 N1 C3 122.3(3) . 2_655 ?
C3 N1 Ni1 118.83(16) . . ?
C3 N1 Ni1 118.84(16) 2_655 . ?
C4 N2 C6 121.5(2) . . ?
C4 N2 Ni1 114.67(18) . . ?
C6 N2 Ni1 123.65(17) . . ?
C2 C1 C2 120.9(4) 2_655 . ?
C2 C1 H1 119.6 2_655 . ?
C2 C1 H1 119.6 . . ?
C1 C2 C3 118.3(3) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
N1 C3 C2 120.1(3) . . ?
N1 C3 C4 113.5(2) . . ?
C2 C3 C4 126.4(3) . . ?
N2 C4 C3 114.8(2) . . ?
N2 C4 C5 125.4(3) . . ?
C3 C4 C5 119.8(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C11 119.8(3) . . ?
C7 C6 N2 120.7(3) . . ?
C11 C6 N2 119.3(3) . . ?
C6 C7 C8 119.5(4) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 121.2(4) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C10 C9 C8 119.0(3) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 120.6(4) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C6 C11 C10 119.9(4) . . ?
C6 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?

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
C2 C1 C2 C3 -0.5(2) 2_655 . . . ?
C3 N1 C3 C2 -0.5(2) 2_655 . . . ?
Ni1 N1 C3 C2 179.5(2) . . . . ?
C3 N1 C3 C4 180.0(4) 2_655 . . . ?
Ni1 N1 C3 C4 0.0(4) . . . . ?
C1 C2 C3 N1 1.0(4) . . . . ?
C1 C2 C3 C4 -179.6(5) . . . . ?
C6 N2 C4 C3 178.6(3) . . . . ?
Ni1 N2 C4 C3 2.8(4) . . . . ?
C6 N2 C4 C5 -1.5(5) . . . . ?
Ni1 N2 C4 C5 -177.3(3) . . . . ?
N1 C3 C4 N2 -1.9(5) . . . . ?
C2 C3 C4 N2 178.6(3) . . . . ?
N1 C3 C4 C5 178.1(3) . . . . ?
C2 C3 C4 C5 -1.3(5) . . . . ?
C4 N2 C6 C7 -77.1(4) . . . . ?
Ni1 N2 C6 C7 98.3(3) . . . . ?
C4 N2 C6 C11 107.8(4) . . . . ?
Ni1 N2 C6 C11 -76.8(4) . . . . ?
C11 C6 C7 C8 0.0(7) . . . . ?
N2 C6 C7 C8 -175.0(4) . . . . ?
C6 C7 C8 C9 -0.6(7) . . . . ?
C7 C8 C9 C10 0.3(7) . . . . ?
C8 C9 C10 C11 0.5(6) . . . . ?
C7 C6 C11 C10 0.8(7) . . . . ?
N2 C6 C11 C10 175.9(3) . . . . ?
C9 C10 C11 C6 -1.1(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5B Br1 0.97 2.97 3.790(4) 143.3 3_445 yes
C11 H11 Br1 0.94 3.07 3.665(4) 123.1 . yes

_refine_diff_density_max         0.481
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.069

