# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_f1
_database_code_depnum_ccdc_archive 'CCDC 2494093'
loop_
_audit_author_name
_audit_author_address
'Paula Brandao'
;CICECO, Universidade de Aveiro
Portugal
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-04-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H28 Br2 N4 Ni O2'
_chemical_formula_weight         599.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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      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                   9.7151(18)
_cell_length_b                   12.546(3)
_cell_length_c                   10.899(2)
_cell_angle_alpha                90
_cell_angle_beta                 116.138(6)
_cell_angle_gamma                90
_cell_volume                     1192.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    820
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      25.00

_exptl_crystal_description       Block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_F_000             604
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    4.190
_shelx_estimated_absorpt_T_min   0.366
_shelx_estimated_absorpt_T_max   0.730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5438
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29616
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0946
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.640
_diffrn_reflns_theta_max         28.303
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             2890
_reflns_number_gt                2512
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0518P)²+1.3262P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2890
_refine_ls_number_parameters     143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1225
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
Ni1 Ni 0.500000 0.500000 0.500000 0.02647(15) Uani 1 2 d S . P . .
Br1 Br -0.32021(4) 0.49654(3) 0.01036(4) 0.05941(17) Uani 1 1 d . . . . .
O1 O 0.3480(2) 0.59467(13) 0.35037(17) 0.0341(4) Uani 1 1 d . . . . .
N1 N 0.3904(2) 0.37218(15) 0.3773(2) 0.0324(4) Uani 1 1 d . . . . .
N2 N 0.6360(3) 0.49412(16) 0.3831(2) 0.0368(5) Uani 1 1 d . . . . .
C1 C 0.2062(3) 0.57058(19) 0.2757(2) 0.0305(5) Uani 1 1 d . . . . .
C2 C 0.0941(3) 0.6528(2) 0.2221(3) 0.0392(5) Uani 1 1 d . . . . .
H2 H 0.125250 0.723450 0.240701 0.047 Uiso 1 1 calc R U . . .
C3 C -0.0586(3) 0.6310(2) 0.1439(3) 0.0440(6) Uani 1 1 d . . . . .
H3 H -0.129055 0.686565 0.111687 0.053 Uiso 1 1 calc R U . . .
C4 C -0.1080(3) 0.5263(3) 0.1128(3) 0.0407(6) Uani 1 1 d . . . . .
C5 C -0.0048(3) 0.4439(2) 0.1576(3) 0.0377(5) Uani 1 1 d . . . . .
H5 H -0.038715 0.374368 0.132926 0.045 Uiso 1 1 calc R U . . .
C6 C 0.1512(3) 0.4633(2) 0.2401(2) 0.0328(5) Uani 1 1 d . . . . .
C7 C 0.2544(3) 0.37278(19) 0.2804(3) 0.0359(5) Uani 1 1 d . . . . .
H7A H 0.200148 0.315794 0.300776 0.043 Uiso 1 1 calc R U . . .
H7B H 0.263691 0.350943 0.199023 0.043 Uiso 1 1 calc R U . . .
C8 C 0.4857(3) 0.27798(19) 0.3899(3) 0.0415(6) Uani 1 1 d . . . . .
H8A H 0.420804 0.216726 0.348476 0.050 Uiso 1 1 calc R U . . .
H8B H 0.549246 0.262236 0.485560 0.050 Uiso 1 1 calc R U . . .
C9 C 0.5863(4) 0.3003(2) 0.3183(3) 0.0521(7) Uani 1 1 d . . . . .
H9A H 0.520512 0.318408 0.223839 0.062 Uiso 1 1 calc R U . . .
H9B H 0.640233 0.235221 0.318207 0.062 Uiso 1 1 calc R U . . .
C10 C 0.7037(4) 0.3887(2) 0.3803(3) 0.0470(7) Uani 1 1 d . . . . .
H10A H 0.773809 0.368901 0.473025 0.056 Uiso 1 1 calc R U . . .
H10B H 0.762801 0.394969 0.328470 0.056 Uiso 1 1 calc R U . . .
C11 C 0.7494(4) 0.5791(3) 0.4107(3) 0.0491(7) Uani 1 1 d . . . . .
H11A H 0.834171 0.567722 0.498608 0.074 Uiso 1 1 calc R U . . .
H11B H 0.702927 0.646782 0.409970 0.074 Uiso 1 1 calc R U . . .
H11C H 0.785361 0.578481 0.341563 0.074 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
Ni1 O1 2.0321(17) . ?
Ni1 O1 2.0321(17) 3_666 ?
Ni1 N1 2.059(2) 3_666 ?
Ni1 N1 2.059(2) . ?
Ni1 N2 2.204(2) 3_666 ?
Ni1 N2 2.204(2) . ?
Br1 C4 1.899(3) . ?
O1 C1 1.289(3) . ?
N1 C7 1.278(3) . ?
N1 C8 1.470(3) . ?
N2 C11 1.466(4) . ?
N2 C10 1.483(3) . ?
C1 C2 1.425(3) . ?
C1 C6 1.437(3) . ?
C2 C3 1.374(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(4) . ?
C5 C6 1.401(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.449(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.521(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.519(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
O1 Ni1 O1 180.00(8) . 3_666 ?
O1 Ni1 N1 92.92(7) . 3_666 ?
O1 Ni1 N1 87.08(7) 3_666 3_666 ?
O1 Ni1 N1 87.08(7) . . ?
O1 Ni1 N1 92.92(7) 3_666 . ?
N1 Ni1 N1 180.00(12) 3_666 . ?
O1 Ni1 N2 92.04(8) . 3_666 ?
O1 Ni1 N2 87.96(8) 3_666 3_666 ?
N1 Ni1 N2 82.44(8) 3_666 3_666 ?
N1 Ni1 N2 97.56(8) . 3_666 ?
O1 Ni1 N2 87.96(8) . . ?
O1 Ni1 N2 92.04(8) 3_666 . ?
N1 Ni1 N2 97.56(8) 3_666 . ?
N1 Ni1 N2 82.44(8) . . ?
N2 Ni1 N2 180.0 3_666 . ?
C1 O1 Ni1 124.48(15) . . ?
C7 N1 C8 117.5(2) . . ?
C7 N1 Ni1 125.65(16) . . ?
C8 N1 Ni1 116.21(16) . . ?
C11 N2 C10 110.7(2) . . ?
C11 N2 Ni1 116.40(17) . . ?
C10 N2 Ni1 115.20(16) . . ?
O1 C1 C2 120.0(2) . . ?
O1 C1 C6 123.8(2) . . ?
C2 C1 C6 116.1(2) . . ?
C3 C2 C1 122.2(3) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 Br1 119.7(2) . . ?
C3 C4 Br1 119.9(2) . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 C7 117.8(2) . . ?
C1 C6 C7 121.8(2) . . ?
N1 C7 C6 125.5(2) . . ?
N1 C7 H7A 105.9 . . ?
C6 C7 H7A 105.9 . . ?
N1 C7 H7B 105.9 . . ?
C6 C7 H7B 105.9 . . ?
H7A C7 H7B 106.3 . . ?
N1 C8 C9 109.0(2) . . ?
N1 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
N1 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C8 C9 C10 115.6(2) . . ?
C8 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
C10 C9 H9B 108.4 . . ?
H9A C9 H9B 107.4 . . ?
N2 C10 C9 114.1(2) . . ?
N2 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
N2 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_refine_diff_density_max         0.985
_refine_diff_density_min         -0.946
_refine_diff_density_rms         0.073

