# Supplementary Information (SI) for RSC Sustainability.
# This journal is © The Royal Society of Chemistry 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_20231011b
_database_code_depnum_ccdc_archive 'CCDC 2307070'
loop_
_audit_author_name
_audit_author_address
'congcong zhang '
;SDAU
China
;
_audit_update_record             
;
2023-11-10 deposited with the CCDC.	2024-10-14 downloaded from the CCDC.
;
_audit_creation_date             2023-10-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H28 Br2 N4 Ni'
_chemical_formula_sum            'C20 H28 Br2 N4 Ni'
_chemical_formula_weight         542.99
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1N1Ni1Br1
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'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   9.1561(3)
_cell_length_b                   9.1561(3)
_cell_length_c                   23.8743(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2001.48(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2066
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      27.5990
_cell_measurement_theta_min      3.5680
_shelx_estimated_absorpt_T_max   0.522
_shelx_estimated_absorpt_T_min   0.436
_exptl_absorpt_coefficient_mu    4.975
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.802
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            5584
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.713
_diffrn_reflns_theta_min         3.413
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     41.00  92.00   1.00    3.00    --   12.76 178.00 150.00   51
  2  ω     44.00  99.00   1.00    3.00    --   12.76-178.00 -30.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0125975000
_diffrn_orient_matrix_UB_12      -0.0763265000
_diffrn_orient_matrix_UB_13      0.0018256000
_diffrn_orient_matrix_UB_21      -0.0641166000
_diffrn_orient_matrix_UB_22      0.0078742000
_diffrn_orient_matrix_UB_23      -0.0163744000
_diffrn_orient_matrix_UB_31      0.0415558000
_diffrn_orient_matrix_UB_32      -0.0108662000
_diffrn_orient_matrix_UB_33      -0.0247232000
_diffrn_oxdiff_digest_frames     
;
01f95212ef8b1a6cb2877c7af4ea265ee900114aa03
;
_diffrn_oxdiff_digest_hkl        
;
01a3d0d04d1b6b16ad1ca8efbb1844053c6f95
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.577
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.789
_reflns_number_gt                2215
_reflns_number_total             2427
_reflns_odcompleteness_completeness 99.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.110
_refine_ls_abs_structure_details 
;
 Flack x determined using 732 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.013(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2427
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0067P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0662
_refine_ls_wR_factor_ref         0.0685
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.52512(5) 0.29464(5) 0.45380(2) 0.01299(14) Uani 1 1 d . . . . .
C1 C 0.6221(5) 0.4221(5) 0.61786(18) 0.0106(10) Uani 1 1 d . . . . .
H1 H 0.5233 0.4414 0.6275 0.013 Uiso 1 1 calc R . . . .
C2 C 0.7149(6) 0.3652(5) 0.6582(2) 0.0134(11) Uani 1 1 d . . . . .
H2 H 0.6786 0.3438 0.6945 0.016 Uiso 1 1 calc R . . . .
C3 C 0.8591(5) 0.3396(5) 0.6458(2) 0.0123(10) Uani 1 1 d . . . . .
H3 H 0.9236 0.3009 0.6732 0.015 Uiso 1 1 calc R . . . .
C4 C 0.9086(5) 0.3719(5) 0.5918(2) 0.0122(11) Uani 1 1 d . . . . .
H4 H 1.0084 0.3589 0.5821 0.015 Uiso 1 1 calc R . . . .
C5 C 0.8096(5) 0.4228(5) 0.55309(18) 0.0075(9) Uani 1 1 d . . . . .
C6 C 0.8522(5) 0.4502(5) 0.49329(19) 0.0102(10) Uani 1 1 d . . . . .
H6A H 0.9585 0.4688 0.4910 0.012 Uiso 1 1 calc R . . . .
H6B H 0.8296 0.3631 0.4703 0.012 Uiso 1 1 calc R . . . .
C7 C 0.7816(5) 0.5802(5) 0.40943(17) 0.0112(10) Uani 1 1 d . . . . .
H7A H 0.7275 0.4970 0.3940 0.017 Uiso 1 1 calc GR . . . .
H7B H 0.8844 0.5733 0.3983 0.017 Uiso 1 1 calc GR . . . .
H7C H 0.7400 0.6714 0.3950 0.017 Uiso 1 1 calc GR . . . .
C8 C 0.8312(5) 0.7143(5) 0.4984(2) 0.0093(10) Uani 1 1 d . . . . .
H8 H 0.8574 0.6879 0.5378 0.011 Uiso 1 1 calc R . . . .
C9 C 0.9701(5) 0.7718(5) 0.47057(19) 0.0102(10) Uani 1 1 d . . . . .
H9A H 1.0464 0.6953 0.4717 0.012 Uiso 1 1 calc R . . . .
H9B H 0.9496 0.7945 0.4308 0.012 Uiso 1 1 calc R . . . .
C10 C 1.0257(5) 0.9076(5) 0.4997(2) 0.0119(10) Uani 1 1 d . . . . .
H10A H 1.1132 0.9446 0.4799 0.014 Uiso 1 1 calc R . . . .
H10B H 1.0543 0.8833 0.5385 0.014 Uiso 1 1 calc R . . . .
N1 N 0.6682(4) 0.4509(4) 0.56542(14) 0.0086(8) Uani 1 1 d . . . . .
N2 N 0.7707(4) 0.5786(4) 0.47140(15) 0.0075(8) Uani 1 1 d . . . . .
Ni1 Ni 0.54904(7) 0.54904(7) 0.5000 0.0077(2) Uani 1 2 d S T P . .


_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 2.5866(7) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(7) . ?
C1 N1 1.347(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.374(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(6) . ?
C5 C6 1.501(6) . ?
C5 N1 1.352(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 N2 1.487(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 N2 1.483(5) . ?
C8 C8 1.516(9) 7_556 ?
C8 H8 1.0000 . ?
C8 C9 1.528(6) . ?
C8 N2 1.505(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.513(6) . ?
C10 C10 1.530(9) 7_556 ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N1 Ni1 2.107(4) . ?
N2 Ni1 2.158(4) . ?
Ni1 Br1 2.5866(7) 7_556 ?
Ni1 N1 2.107(4) 7_556 ?
Ni1 N2 2.158(4) 7_556 ?

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
C2 C1 H1 119.1 . . ?
N1 C1 H1 119.1 . . ?
N1 C1 C2 121.8(4) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.3(5) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.3(5) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.5(4) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C6 121.6(4) . . ?
N1 C5 C4 123.3(4) . . ?
N1 C5 C6 115.1(4) . . ?
C5 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C6 C5 109.6(4) . . ?
N2 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
C8 C8 H8 107.0 7_556 . ?
C8 C8 C9 111.5(3) 7_556 . ?
C9 C8 H8 107.0 . . ?
N2 C8 C8 110.2(3) . 7_556 ?
N2 C8 H8 107.0 . . ?
N2 C8 C9 113.9(4) . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 111.4(4) . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C9 C10 C10 110.4(3) . 7_556 ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C10 C10 H10A 109.6 7_556 . ?
C10 C10 H10B 109.6 7_556 . ?
H10A C10 H10B 108.1 . . ?
C1 N1 C5 117.7(4) . . ?
C1 N1 Ni1 127.6(3) . . ?
C5 N1 Ni1 114.6(3) . . ?
C6 N2 C8 108.5(3) . . ?
C6 N2 Ni1 105.2(3) . . ?
C7 N2 C6 109.0(3) . . ?
C7 N2 C8 113.2(4) . . ?
C7 N2 Ni1 112.3(3) . . ?
C8 N2 Ni1 108.3(3) . . ?
Br1 Ni1 Br1 91.68(3) . 7_556 ?
N1 Ni1 Br1 88.62(10) 7_556 7_556 ?
N1 Ni1 Br1 96.56(10) 7_556 . ?
N1 Ni1 Br1 88.61(10) . . ?
N1 Ni1 Br1 96.55(10) . 7_556 ?
N1 Ni1 N1 172.6(2) . 7_556 ?
N1 Ni1 N2 78.52(14) . . ?
N1 Ni1 N2 78.52(14) 7_556 7_556 ?
N1 Ni1 N2 95.84(14) . 7_556 ?
N1 Ni1 N2 95.84(14) 7_556 . ?
N2 Ni1 Br1 93.30(10) 7_556 7_556 ?
N2 Ni1 Br1 172.90(10) 7_556 . ?
N2 Ni1 Br1 93.30(9) . . ?
N2 Ni1 Br1 172.90(10) . 7_556 ?
N2 Ni1 N2 82.20(19) . 7_556 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.110
_oxdiff_exptl_absorpt_empirical_full_min 0.863
