# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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_f
_database_code_depnum_ccdc_archive 'CCDC 2261269'
loop_
_audit_author_name
_audit_author_address
'Paula Brandao'
;Department of Chemistry CICECO Aveiro Institute of Materials Portugal
Portugal
;
_audit_update_record             
;
2023-05-07 deposited with the CCDC.	2024-04-29 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            'C30 H24 Br4 N2 Ni O2'
_chemical_formula_weight         822.86

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           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   14.0430(13)
_cell_length_b                   10.9134(10)
_cell_length_c                   10.1076(10)
_cell_angle_alpha                90
_cell_angle_beta                 116.942(3)
_cell_angle_gamma                90
_cell_volume                     1380.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    604
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      25.14

_exptl_crystal_description       Block
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.979
_exptl_crystal_F_000             804
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    6.522
_shelx_estimated_absorpt_T_min   0.355
_shelx_estimated_absorpt_T_max   0.696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4182
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'photon 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10699
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.476
_diffrn_reflns_theta_max         27.120
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             2948
_reflns_number_gt                2697
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_max     0.947
_reflns_Friedel_fraction_full    0.950

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al 2008)'
_computing_publication_material  'SHELXL-2016/4 (Sheldrick, 2016)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0529P)²+5.4860P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.14(2)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2948
_refine_ls_number_parameters     183
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
Br1 Br 0.16932(7) 0.77473(7) 0.11489(9) 0.0249(2) Uani 1 1 d . . . . .
Br2 Br -0.04911(7) 0.41765(8) 0.28311(10) 0.0302(3) Uani 1 1 d . . . . .
Ni1 Ni 0.500000 0.62208(13) 0.500000 0.0200(3) Uani 1 2 d S T P . .
O1 O 0.3573(5) 0.6775(5) 0.3845(7) 0.0227(13) Uani 1 1 d . . . . .
N1 N 0.4603(6) 0.5238(6) 0.6367(8) 0.0193(14) Uani 1 1 d . . . . .
C1 C 0.2699(7) 0.6234(7) 0.3694(9) 0.0199(16) Uani 1 1 d . . . . .
C2 C 0.1706(7) 0.6535(7) 0.2548(9) 0.0197(17) Uani 1 1 d . . . . .
C3 C 0.0756(7) 0.6000(8) 0.2274(9) 0.0233(18) Uani 1 1 d . . . . .
H3 H 0.010154 0.625683 0.147515 0.028 Uiso 1 1 calc R U . . .
C4 C 0.0795(7) 0.5039(8) 0.3246(10) 0.0220(17) Uani 1 1 d . . . . .
C5 C 0.1720(7) 0.4708(8) 0.4404(10) 0.0235(18) Uani 1 1 d . . . . .
H5 H 0.172595 0.407479 0.505246 0.028 Uiso 1 1 calc R U . . .
C6 C 0.2677(7) 0.5294(7) 0.4656(9) 0.0180(16) Uani 1 1 d . . . . .
C7 C 0.3640(7) 0.4912(8) 0.5965(9) 0.0207(17) Uani 1 1 d . . . . .
H7 H 0.353444 0.434568 0.660011 0.025 Uiso 1 1 calc R U . . .
C8 C 0.5390(8) 0.4825(8) 0.7868(10) 0.0237(18) Uani 1 1 d . . . . .
H8 H 0.494(7) 0.423(9) 0.830(9) 0.01(2) Uiso 1 1 d . . . . .
C9 C 0.5825(8) 0.5924(9) 0.8892(10) 0.028(2) Uani 1 1 d . . . . .
H9A H 0.626906 0.641961 0.857769 0.042 Uiso 1 1 calc R U . . .
H9B H 0.625799 0.564062 0.991206 0.042 Uiso 1 1 calc R U . . .
H9C H 0.523015 0.642147 0.884624 0.042 Uiso 1 1 calc R U . . .
C10 C 0.6250(7) 0.4038(8) 0.7780(9) 0.0215(17) Uani 1 1 d . . . . .
C11 C 0.7342(7) 0.4230(8) 0.8642(9) 0.0223(16) Uani 1 1 d . . . . .
H11 H 0.758216 0.491511 0.928988 0.027 Uiso 1 1 calc R U . . .
C12 C 0.8082(8) 0.3427(9) 0.8561(10) 0.029(2) Uani 1 1 d . . . . .
H12 H 0.882285 0.355600 0.917671 0.035 Uiso 1 1 calc R U . . .
C13 C 0.7754(9) 0.2449(9) 0.7598(11) 0.036(2) Uani 1 1 d . . . . .
H13 H 0.826602 0.191770 0.753018 0.043 Uiso 1 1 calc R U . . .
C14 C 0.6688(10) 0.2244(9) 0.6740(13) 0.038(2) Uani 1 1 d . . . . .
H14 H 0.646555 0.157551 0.606434 0.046 Uiso 1 1 calc R U . . .
C15 C 0.5912(8) 0.3004(8) 0.6839(10) 0.029(2) Uani 1 1 d . . . . .
H15 H 0.517353 0.282420 0.628145 0.035 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 C2 1.931(8) . ?
Br2 C4 1.907(8) . ?
Ni1 O1 1.903(6) . ?
Ni1 O1 1.903(6) 2_656 ?
Ni1 N1 2.017(7) 2_656 ?
Ni1 N1 2.017(7) . ?
O1 C1 1.307(10) . ?
N1 C7 1.274(12) . ?
N1 C8 1.485(11) . ?
C1 C2 1.390(12) . ?
C1 C6 1.424(11) . ?
C2 C3 1.365(13) . ?
C3 C4 1.420(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.346(13) . ?
C5 C6 1.403(12) . ?
C5 H5 0.9500 . ?
C6 C7 1.460(12) . ?
C7 H7 0.9500 . ?
C8 C10 1.518(12) . ?
C8 C9 1.520(13) . ?
C8 H8 1.12(9) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.394(13) . ?
C10 C15 1.412(13) . ?
C11 C12 1.389(13) . ?
C11 H11 0.9500 . ?
C12 C13 1.376(14) . ?
C12 H12 0.9500 . ?
C13 C14 1.366(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.408(15) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

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 143.0(4) . 2_656 ?
O1 Ni1 N1 106.8(3) . 2_656 ?
O1 Ni1 N1 92.8(3) 2_656 2_656 ?
O1 Ni1 N1 92.8(3) . . ?
O1 Ni1 N1 106.8(3) 2_656 . ?
N1 Ni1 N1 115.8(4) 2_656 . ?
C1 O1 Ni1 126.9(5) . . ?
C7 N1 C8 115.6(7) . . ?
C7 N1 Ni1 120.8(6) . . ?
C8 N1 Ni1 123.6(6) . . ?
O1 C1 C2 121.7(8) . . ?
O1 C1 C6 123.7(8) . . ?
C2 C1 C6 114.5(8) . . ?
C3 C2 C1 126.0(8) . . ?
C3 C2 Br1 117.5(6) . . ?
C1 C2 Br1 116.4(6) . . ?
C2 C3 C4 116.6(8) . . ?
C2 C3 H3 121.7 . . ?
C4 C3 H3 121.7 . . ?
C5 C4 C3 121.3(8) . . ?
C5 C4 Br2 120.2(7) . . ?
C3 C4 Br2 118.4(7) . . ?
C4 C5 C6 120.2(8) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 121.3(8) . . ?
C5 C6 C7 116.9(7) . . ?
C1 C6 C7 121.8(8) . . ?
N1 C7 C6 128.6(8) . . ?
N1 C7 H7 115.7 . . ?
C6 C7 H7 115.7 . . ?
N1 C8 C10 110.8(7) . . ?
N1 C8 C9 109.9(7) . . ?
C10 C8 C9 113.7(8) . . ?
N1 C8 H8 106(5) . . ?
C10 C8 H8 108(5) . . ?
C9 C8 H8 108(4) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 118.7(8) . . ?
C11 C10 C8 123.9(8) . . ?
C15 C10 C8 117.3(8) . . ?
C12 C11 C10 120.6(8) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 120.7(10) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 119.7(10) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 121.2(10) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C10 118.9(9) . . ?
C14 C15 H15 120.5 . . ?
C10 C15 H15 120.5 . . ?

_refine_diff_density_max         1.470
_refine_diff_density_min         -0.838
_refine_diff_density_rms         0.145

