# Supplementary Information (SI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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. 
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data_BTCB24_S_Ag_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2261474'
loop_
_audit_author_name
_audit_author_address
'Barbara Tirloni'
;Universidade Federal de Santa Maria
Brazil
;
_audit_update_record             
;
2023-05-08 deposited with the CCDC.	2025-06-05 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Br2 N4 Ni O2 Se'
_chemical_formula_sum            'C20 H16 Br2 N4 Ni O2 Se'
_chemical_formula_weight         641.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.1811 1.6452 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3147 0.7232 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se 0.2367 1.4831 '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                   14.0502(5)
_cell_length_b                   10.1635(3)
_cell_length_c                   15.1056(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.4760(10)
_cell_angle_gamma                90
_cell_volume                     2150.49(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9978
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      22.66
_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.982
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.045
_exptl_absorpt_coefficient_mu    3.374
_shelx_estimated_absorpt_T_min   0.633
_shelx_estimated_absorpt_T_max   0.863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6363
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_process_details   
; SADABS (version 2014/5; Bruker, 2014) was used to perform the
multi-scan absorption correction.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.56086
_diffrn_radiation_type           AgK\a
_diffrn_source                   'microfocus X ray tube'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            77378
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.657
_diffrn_reflns_theta_max         23.639
_diffrn_reflns_theta_full        19.665
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6551
_reflns_number_gt                4921
_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       'APEX3 v2015.5-2 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond (version 3.2i)'
_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)+(0.0216P)²+2.4209P] 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         6551
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0719
_refine_ls_wR_factor_gt          0.0648
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
SE1 Se 0.21301(2) 0.71923(3) 0.48122(2) 0.03733(7) Uani 1 1 d . . . . .
O1 O 0.27951(14) 0.6701(2) 0.40138(14) 0.0421(5) Uani 1 1 d . . . . .
BR1 Br 0.10353(2) 0.46999(3) 0.43190(2) 0.04089(8) Uani 1 1 d . . . . .
NI1 Ni 0.24836(2) 0.48662(3) 0.33958(2) 0.02953(8) Uani 1 1 d . . . . .
C1 C 0.3239(2) 0.3468(3) 0.51089(19) 0.0427(7) Uani 1 1 d . . . . .
H1 H 0.261200 0.349315 0.526424 0.051 Uiso 1 1 calc R U . . .
N1 N 0.34345(15) 0.3928(2) 0.43149(14) 0.0323(5) Uani 1 1 d . . . . .
C2 C 0.3935(2) 0.2957(3) 0.5707(2) 0.0461(7) Uani 1 1 d . . . . .
H2 H 0.377620 0.263210 0.625226 0.055 Uiso 1 1 calc R U . . .
N2 N 0.37415(16) 0.4983(2) 0.27662(15) 0.0325(5) Uani 1 1 d . . . . .
BR2 Br 0.25190(3) 0.96983(4) 0.47321(2) 0.06172(11) Uani 1 1 d . . . . .
O2 O 0.26863(16) 0.6790(3) 0.57546(14) 0.0529(6) Uani 1 1 d . . . . .
C3 C 0.4862(2) 0.2933(3) 0.5488(2) 0.0448(7) Uani 1 1 d . . . . .
H3 H 0.534353 0.261359 0.588857 0.054 Uiso 1 1 calc R U . . .
N3 N 0.20580(16) 0.3182(2) 0.26864(15) 0.0333(5) Uani 1 1 d . . . . .
C4 C 0.5072(2) 0.3389(3) 0.4668(2) 0.0390(6) Uani 1 1 d . . . . .
H4 H 0.569611 0.336998 0.450276 0.047 Uiso 1 1 calc R U . . .
N4 N 0.15818(16) 0.5653(2) 0.23804(15) 0.0358(5) Uani 1 1 d . . . . .
C5 C 0.43413(18) 0.3877(3) 0.40903(17) 0.0302(5) Uani 1 1 d . . . . .
C9 C 0.4666(3) 0.5382(3) 0.1537(2) 0.0502(8) Uani 1 1 d . . . . .
H9 H 0.470506 0.572338 0.096944 0.060 Uiso 1 1 calc R U . . .
C8 C 0.5442(2) 0.4768(3) 0.1973(2) 0.0496(8) Uani 1 1 d . . . . .
H8 H 0.601127 0.468806 0.170226 0.060 Uiso 1 1 calc R U . . .
C7 C 0.5365(2) 0.4273(3) 0.2814(2) 0.0436(7) Uani 1 1 d . . . . .
H7 H 0.588341 0.386465 0.312073 0.052 Uiso 1 1 calc R U . . .
C6 C 0.45032(18) 0.4392(3) 0.31960(18) 0.0310(5) Uani 1 1 d . . . . .
C10 C 0.3830(2) 0.5481(3) 0.19542(19) 0.0419(7) Uani 1 1 d . . . . .
H10 H 0.331003 0.590844 0.166308 0.050 Uiso 1 1 calc R U . . .
C11 C 0.2366(2) 0.1967(3) 0.2851(2) 0.0433(7) Uani 1 1 d . . . . .
H11 H 0.282165 0.182891 0.332233 0.052 Uiso 1 1 calc R U . . .
C12 C 0.2037(3) 0.0890(3) 0.2350(2) 0.0502(8) Uani 1 1 d . . . . .
H12 H 0.227069 0.005062 0.247970 0.060 Uiso 1 1 calc R U . . .
C13 C 0.1360(3) 0.1092(4) 0.1661(2) 0.0518(8) Uani 1 1 d . . . . .
H13 H 0.112564 0.038901 0.131554 0.062 Uiso 1 1 calc R U . . .
C14 C 0.1033(2) 0.2346(3) 0.1486(2) 0.0481(8) Uani 1 1 d . . . . .
H14 H 0.057605 0.249720 0.101744 0.058 Uiso 1 1 calc R U . . .
C15 C 0.1384(2) 0.3384(3) 0.20079(17) 0.0351(6) Uani 1 1 d . . . . .
C16 C 0.10731(19) 0.4762(3) 0.18834(17) 0.0359(6) Uani 1 1 d . . . . .
C17 C 0.0294(2) 0.5133(4) 0.1317(2) 0.0508(8) Uani 1 1 d . . . . .
H17 H -0.005841 0.450233 0.098709 0.061 Uiso 1 1 calc R U . . .
C18 C 0.0048(2) 0.6440(4) 0.1248(2) 0.0575(9) Uani 1 1 d . . . . .
H18 H -0.047204 0.670467 0.087064 0.069 Uiso 1 1 calc R U . . .
C19 C 0.0581(3) 0.7353(4) 0.1743(2) 0.0550(9) Uani 1 1 d . . . . .
H19 H 0.043081 0.824292 0.170130 0.066 Uiso 1 1 calc R U . . .
C20 C 0.1340(2) 0.6925(3) 0.2301(2) 0.0454(7) Uani 1 1 d . . . . .
H20 H 0.169824 0.754321 0.263653 0.054 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
SE1 O2 1.622(2) . ?
SE1 O1 1.659(2) . ?
SE1 BR2 2.6097(5) . ?
O1 NI1 2.116(2) . ?
BR1 NI1 2.5606(4) . ?
NI1 N4 2.072(2) . ?
NI1 N2 2.075(2) . ?
NI1 N1 2.081(2) . ?
NI1 N3 2.082(2) . ?
C1 N1 1.336(4) . ?
C1 C2 1.380(4) . ?
C1 H1 0.9300 . ?
N1 C5 1.345(3) . ?
C2 C3 1.369(5) . ?
C2 H2 0.9300 . ?
N2 C10 1.342(4) . ?
N2 C6 1.349(3) . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
N3 C11 1.326(4) . ?
N3 C15 1.356(3) . ?
C4 C5 1.386(4) . ?
C4 H4 0.9300 . ?
N4 C20 1.339(4) . ?
N4 C16 1.346(4) . ?
C5 C6 1.483(4) . ?
C9 C8 1.378(5) . ?
C9 C10 1.380(4) . ?
C9 H9 0.9300 . ?
C8 C7 1.379(5) . ?
C8 H8 0.9300 . ?
C7 C6 1.386(4) . ?
C7 H7 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.389(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.474(4) . ?
C16 C17 1.388(4) . ?
C17 C18 1.375(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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
O2 SE1 O1 107.58(11) . . ?
O2 SE1 BR2 101.46(9) . . ?
O1 SE1 BR2 97.35(8) . . ?
SE1 O1 NI1 118.49(11) . . ?
N4 NI1 N2 97.59(9) . . ?
N4 NI1 N1 173.77(9) . . ?
N2 NI1 N1 78.85(9) . . ?
N4 NI1 N3 78.57(9) . . ?
N2 NI1 N3 91.82(9) . . ?
N1 NI1 N3 96.34(9) . . ?
N4 NI1 O1 94.57(9) . . ?
N2 NI1 O1 89.86(8) . . ?
N1 NI1 O1 90.55(9) . . ?
N3 NI1 O1 173.10(9) . . ?
N4 NI1 BR1 87.85(7) . . ?
N2 NI1 BR1 174.27(6) . . ?
N1 NI1 BR1 95.89(6) . . ?
N3 NI1 BR1 91.00(6) . . ?
O1 NI1 BR1 87.92(6) . . ?
N1 C1 C2 122.4(3) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 N1 C5 118.6(2) . . ?
C1 N1 NI1 126.39(19) . . ?
C5 N1 NI1 114.89(18) . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C10 N2 C6 118.8(2) . . ?
C10 N2 NI1 125.7(2) . . ?
C6 N2 NI1 115.22(18) . . ?
C2 C3 C4 119.1(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C11 N3 C15 118.8(2) . . ?
C11 N3 NI1 126.35(19) . . ?
C15 N3 NI1 114.84(19) . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C20 N4 C16 118.7(3) . . ?
C20 N4 NI1 125.1(2) . . ?
C16 N4 NI1 114.87(19) . . ?
N1 C5 C4 121.7(3) . . ?
N1 C5 C6 115.6(2) . . ?
C4 C5 C6 122.7(2) . . ?
C8 C9 C10 119.0(3) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C9 C8 C7 119.3(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C7 C6 119.0(3) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
N2 C6 C7 121.6(3) . . ?
N2 C6 C5 115.0(2) . . ?
C7 C6 C5 123.3(3) . . ?
N2 C10 C9 122.2(3) . . ?
N2 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
N3 C11 C12 122.8(3) . . ?
N3 C11 H11 118.6 . . ?
C12 C11 H11 118.6 . . ?
C13 C12 C11 118.6(3) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C14 119.2(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
N3 C15 C14 120.8(3) . . ?
N3 C15 C16 115.0(2) . . ?
C14 C15 C16 124.2(3) . . ?
N4 C16 C17 121.4(3) . . ?
N4 C16 C15 115.4(2) . . ?
C17 C16 C15 123.2(3) . . ?
C18 C17 C16 119.4(3) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 119.2(3) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C18 C19 C20 118.9(3) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
N4 C20 C19 122.5(3) . . ?
N4 C20 H20 118.7 . . ?
C19 C20 H20 118.7 . . ?

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
O2 SE1 O1 NI1 96.14(14) . . . . ?
BR2 SE1 O1 NI1 -159.32(10) . . . . ?
C2 C1 N1 C5 0.7(5) . . . . ?
C2 C1 N1 NI1 -174.4(2) . . . . ?
N1 C1 C2 C3 0.9(5) . . . . ?
C1 C2 C3 C4 -1.7(5) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C1 N1 C5 C4 -1.4(4) . . . . ?
NI1 N1 C5 C4 174.2(2) . . . . ?
C1 N1 C5 C6 179.4(2) . . . . ?
NI1 N1 C5 C6 -5.0(3) . . . . ?
C3 C4 C5 N1 0.7(4) . . . . ?
C3 C4 C5 C6 179.8(3) . . . . ?
C10 C9 C8 C7 -0.2(5) . . . . ?
C9 C8 C7 C6 0.8(5) . . . . ?
C10 N2 C6 C7 -0.9(4) . . . . ?
NI1 N2 C6 C7 173.3(2) . . . . ?
C10 N2 C6 C5 179.7(2) . . . . ?
NI1 N2 C6 C5 -6.1(3) . . . . ?
C8 C7 C6 N2 -0.2(4) . . . . ?
C8 C7 C6 C5 179.1(3) . . . . ?
N1 C5 C6 N2 7.4(3) . . . . ?
C4 C5 C6 N2 -171.8(3) . . . . ?
N1 C5 C6 C7 -172.0(3) . . . . ?
C4 C5 C6 C7 8.8(4) . . . . ?
C6 N2 C10 C9 1.6(4) . . . . ?
NI1 N2 C10 C9 -172.0(2) . . . . ?
C8 C9 C10 N2 -1.0(5) . . . . ?
C15 N3 C11 C12 0.9(5) . . . . ?
NI1 N3 C11 C12 179.3(2) . . . . ?
N3 C11 C12 C13 -0.5(5) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
C12 C13 C14 C15 -0.4(5) . . . . ?
C11 N3 C15 C14 -1.1(4) . . . . ?
NI1 N3 C15 C14 -179.6(2) . . . . ?
C11 N3 C15 C16 179.0(3) . . . . ?
NI1 N3 C15 C16 0.5(3) . . . . ?
C13 C14 C15 N3 0.8(5) . . . . ?
C13 C14 C15 C16 -179.3(3) . . . . ?
C20 N4 C16 C17 -1.9(4) . . . . ?
NI1 N4 C16 C17 165.3(2) . . . . ?
C20 N4 C16 C15 180.0(3) . . . . ?
NI1 N4 C16 C15 -12.8(3) . . . . ?
N3 C15 C16 N4 8.2(4) . . . . ?
C14 C15 C16 N4 -171.8(3) . . . . ?
N3 C15 C16 C17 -169.9(3) . . . . ?
C14 C15 C16 C17 10.1(5) . . . . ?
N4 C16 C17 C18 1.4(5) . . . . ?
C15 C16 C17 C18 179.3(3) . . . . ?
C16 C17 C18 C19 0.0(5) . . . . ?
C17 C18 C19 C20 -0.7(5) . . . . ?
C16 N4 C20 C19 1.2(5) . . . . ?
NI1 N4 C20 C19 -164.7(3) . . . . ?
C18 C19 C20 N4 0.1(5) . . . . ?

_refine_diff_density_max         0.598
_refine_diff_density_min         -0.834
_refine_diff_density_rms         0.090



####################################################################### 
# 
# 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_BTCB16_S2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2261478'
loop_
_audit_author_name
_audit_author_address
'Barbara Tirloni'
;Universidade Federal de Santa Maria
Brazil
;
_audit_update_record             
;
2023-05-08 deposited with the CCDC.	2025-06-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 Cl N2 Ni0.50 O Se0.50'
_chemical_formula_sum            'C10 H8 Cl N2 Ni0.50 O Se0.50'
_chemical_formula_weight         276.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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'
Cl Cl 0.0998 0.0984 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3147 0.7232 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se 0.2367 1.4831 '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                   13.8108(7)
_cell_length_b                   10.0814(5)
_cell_length_c                   14.8966(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.417(2)
_cell_angle_gamma                90
_cell_volume                     2067.93(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    8438
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      23.02
_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.041
_exptl_absorpt_coefficient_mu    1.571
_shelx_estimated_absorpt_T_min   0.784
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6917
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_process_details   
; SADABS (version 2014/5; Bruker, 2014) was used to perform the
multi-scan absorption correction.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.56086
_diffrn_radiation_type           AgK\a
_diffrn_source                   'microfocus X ray tube'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            63586
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_av_R_equivalents  0.1289
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.164
_diffrn_reflns_theta_max         23.670
_diffrn_reflns_theta_full        19.665
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6340
_reflns_number_gt                4136
_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       'APEX3 v2015.5-2 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond (version 3.2i)'
_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)+(0.0264P)²+1.9411P] 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         6340
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.0865
_refine_ls_wR_factor_gt          0.0743
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
SE1 Se 0.79185(2) 0.72082(3) 0.52250(2) 0.03373(9) Uani 1 1 d . . . . .
O1 O 0.72452(15) 0.6707(2) 0.60331(15) 0.0394(5) Uani 1 1 d . . . . .
CL1 Cl 0.89283(5) 0.47027(9) 0.56970(5) 0.03773(19) Uani 1 1 d . . . . .
C1 C 0.8758(2) 0.6871(3) 0.7757(2) 0.0405(8) Uani 1 1 d . . . . .
H1 H 0.839728 0.750545 0.742502 0.049 Uiso 1 1 calc R U . . .
N1 N 0.85126(17) 0.5595(3) 0.76549(16) 0.0315(6) Uani 1 1 d . . . . .
NI1 Ni 0.75806(3) 0.48280(4) 0.66226(2) 0.02681(10) Uani 1 1 d . . . . .
C3 C 1.0060(3) 0.6350(4) 0.8825(2) 0.0489(10) Uani 1 1 d . . . . .
H3 H 1.059039 0.660226 0.920995 0.059 Uiso 1 1 calc R U . . .
CL3 Cl 0.75088(8) 0.95426(10) 0.53027(7) 0.0568(3) Uani 1 1 d . . . . .
N3 N 0.65991(17) 0.3914(3) 0.56972(16) 0.0296(5) Uani 1 1 d . . . . .
N2 N 0.80101(17) 0.3106(2) 0.73188(16) 0.0294(5) Uani 1 1 d . . . . .
O2 O 0.73595(17) 0.6804(3) 0.42699(15) 0.0474(6) Uani 1 1 d . . . . .
C2 C 0.9529(2) 0.7284(4) 0.8338(2) 0.0468(9) Uani 1 1 d . . . . .
H2 H 0.968309 0.817935 0.839581 0.056 Uiso 1 1 calc R U . . .
C4 C 0.9805(2) 0.5034(4) 0.8741(2) 0.0442(9) Uani 1 1 d . . . . .
H4 H 1.015667 0.438927 0.907291 0.053 Uiso 1 1 calc R U . . .
N4 N 0.63064(18) 0.4939(2) 0.72788(16) 0.0293(5) Uani 1 1 d . . . . .
C5 C 0.9015(2) 0.4678(3) 0.81553(19) 0.0323(7) Uani 1 1 d . . . . .
C9 C 0.8005(3) 0.0788(4) 0.7650(2) 0.0453(9) Uani 1 1 d . . . . .
H9 H 0.775892 -0.005216 0.751157 0.054 Uiso 1 1 calc R U . . .
C8 C 0.8685(3) 0.0977(4) 0.8361(2) 0.0473(9) Uani 1 1 d . . . . .
H8 H 0.890626 0.026246 0.871440 0.057 Uiso 1 1 calc R U . . .
C7 C 0.9033(2) 0.2230(4) 0.8543(2) 0.0409(8) Uani 1 1 d . . . . .
H7 H 0.949666 0.236894 0.901982 0.049 Uiso 1 1 calc R U . . .
C6 C 0.8690(2) 0.3292(3) 0.80141(19) 0.0299(7) Uani 1 1 d . . . . .
C10 C 0.7695(2) 0.1883(3) 0.7142(2) 0.0391(8) Uani 1 1 d . . . . .
H10 H 0.724297 0.175418 0.665430 0.047 Uiso 1 1 calc R U . . .
C11 C 0.6786(2) 0.3471(4) 0.4886(2) 0.0414(8) Uani 1 1 d . . . . .
H11 H 0.742307 0.348816 0.472555 0.050 Uiso 1 1 calc R U . . .
C12 C 0.6070(3) 0.2987(4) 0.4274(2) 0.0436(8) Uani 1 1 d . . . . .
H12 H 0.622656 0.267960 0.371450 0.052 Uiso 1 1 calc R U . . .
C13 C 0.5132(3) 0.2963(3) 0.4497(2) 0.0421(8) Uani 1 1 d . . . . .
H13 H 0.463856 0.265621 0.408977 0.051 Uiso 1 1 calc R U . . .
C14 C 0.4925(2) 0.3405(3) 0.5341(2) 0.0357(7) Uani 1 1 d . . . . .
H14 H 0.429093 0.339056 0.551135 0.043 Uiso 1 1 calc R U . . .
C15 C 0.5675(2) 0.3867(3) 0.59292(19) 0.0275(6) Uani 1 1 d . . . . .
C16 C 0.5524(2) 0.4370(3) 0.6839(2) 0.0297(6) Uani 1 1 d . . . . .
C17 C 0.4646(2) 0.4269(3) 0.7229(2) 0.0405(8) Uani 1 1 d . . . . .
H17 H 0.411146 0.387574 0.691641 0.049 Uiso 1 1 calc R U . . .
C18 C 0.4577(3) 0.4760(4) 0.8089(3) 0.0473(9) Uani 1 1 d . . . . .
H18 H 0.399977 0.468557 0.836802 0.057 Uiso 1 1 calc R U . . .
C19 C 0.5372(3) 0.5360(4) 0.8525(2) 0.0470(9) Uani 1 1 d . . . . .
H19 H 0.533613 0.571186 0.909902 0.056 Uiso 1 1 calc R U . . .
C20 C 0.6224(2) 0.5434(3) 0.8105(2) 0.0391(8) Uani 1 1 d . . . . .
H20 H 0.676007 0.584249 0.840319 0.047 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
SE1 O2 1.618(2) . ?
SE1 O1 1.656(2) . ?
SE1 CL3 2.4253(10) . ?
O1 NI1 2.124(2) . ?
CL1 NI1 2.4035(8) . ?
C1 N1 1.336(4) . ?
C1 C2 1.383(5) . ?
C1 H1 0.9300 . ?
N1 C5 1.346(4) . ?
N1 NI1 2.077(2) . ?
NI1 N3 2.074(2) . ?
NI1 N4 2.081(2) . ?
NI1 N2 2.085(2) . ?
C3 C2 1.367(5) . ?
C3 C4 1.376(5) . ?
C3 H3 0.9300 . ?
N3 C11 1.332(4) . ?
N3 C15 1.348(4) . ?
N2 C10 1.327(4) . ?
N2 C6 1.357(4) . ?
C2 H2 0.9300 . ?
C4 C5 1.390(4) . ?
C4 H4 0.9300 . ?
N4 C20 1.341(4) . ?
N4 C16 1.348(4) . ?
C5 C6 1.478(4) . ?
C9 C8 1.373(5) . ?
C9 C10 1.387(5) . ?
C9 H9 0.9300 . ?
C8 C7 1.371(5) . ?
C8 H8 0.9300 . ?
C7 C6 1.390(4) . ?
C7 H7 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.382(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.362(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.477(4) . ?
C16 C17 1.388(4) . ?
C17 C18 1.385(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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
O2 SE1 O1 107.82(12) . . ?
O2 SE1 CL3 100.89(10) . . ?
O1 SE1 CL3 96.63(8) . . ?
SE1 O1 NI1 117.14(12) . . ?
N1 C1 C2 122.5(3) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C1 N1 C5 118.8(3) . . ?
C1 N1 NI1 125.5(2) . . ?
C5 N1 NI1 114.7(2) . . ?
N3 NI1 N1 173.59(10) . . ?
N3 NI1 N4 78.63(10) . . ?
N1 NI1 N4 97.50(10) . . ?
N3 NI1 N2 96.14(10) . . ?
N1 NI1 N2 78.76(10) . . ?
N4 NI1 N2 91.68(10) . . ?
N3 NI1 O1 90.63(9) . . ?
N1 NI1 O1 94.43(10) . . ?
N4 NI1 O1 88.92(9) . . ?
N2 NI1 O1 173.19(9) . . ?
N3 NI1 CL1 95.21(7) . . ?
N1 NI1 CL1 88.92(7) . . ?
N4 NI1 CL1 173.04(7) . . ?
N2 NI1 CL1 92.20(7) . . ?
O1 NI1 CL1 87.91(6) . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C11 N3 C15 118.3(3) . . ?
C11 N3 NI1 126.2(2) . . ?
C15 N3 NI1 115.34(19) . . ?
C10 N2 C6 118.5(3) . . ?
C10 N2 NI1 126.8(2) . . ?
C6 N2 NI1 114.8(2) . . ?
C3 C2 C1 118.7(4) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C3 C4 C5 119.2(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C20 N4 C16 118.9(3) . . ?
C20 N4 NI1 125.9(2) . . ?
C16 N4 NI1 115.11(19) . . ?
N1 C5 C4 121.1(3) . . ?
N1 C5 C6 115.6(3) . . ?
C4 C5 C6 123.2(3) . . ?
C8 C9 C10 118.3(3) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C7 C8 C9 119.2(3) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C7 C6 119.9(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
N2 C6 C7 120.8(3) . . ?
N2 C6 C5 115.1(3) . . ?
C7 C6 C5 124.1(3) . . ?
N2 C10 C9 123.3(3) . . ?
N2 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
N3 C11 C12 122.6(3) . . ?
N3 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
C13 C12 C11 119.4(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 118.9(3) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C13 C14 C15 119.1(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
N3 C15 C14 121.8(3) . . ?
N3 C15 C16 115.3(2) . . ?
C14 C15 C16 122.9(3) . . ?
N4 C16 C17 121.5(3) . . ?
N4 C16 C15 115.3(2) . . ?
C17 C16 C15 123.3(3) . . ?
C18 C17 C16 119.0(3) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C19 C18 C17 119.1(3) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 119.3(3) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
N4 C20 C19 122.2(3) . . ?
N4 C20 H20 118.9 . . ?
C19 C20 H20 118.9 . . ?

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
O2 SE1 O1 NI1 95.00(15) . . . . ?
CL3 SE1 O1 NI1 -161.29(11) . . . . ?
C2 C1 N1 C5 2.0(5) . . . . ?
C2 C1 N1 NI1 -166.0(2) . . . . ?
C4 C3 C2 C1 -1.4(5) . . . . ?
N1 C1 C2 C3 0.1(5) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C1 N1 C5 C4 -2.8(4) . . . . ?
NI1 N1 C5 C4 166.4(2) . . . . ?
C1 N1 C5 C6 179.1(3) . . . . ?
NI1 N1 C5 C6 -11.6(3) . . . . ?
C3 C4 C5 N1 1.6(5) . . . . ?
C3 C4 C5 C6 179.5(3) . . . . ?
C10 C9 C8 C7 -0.1(5) . . . . ?
C9 C8 C7 C6 0.5(5) . . . . ?
C10 N2 C6 C7 -1.5(4) . . . . ?
NI1 N2 C6 C7 179.1(2) . . . . ?
C10 N2 C6 C5 179.0(3) . . . . ?
NI1 N2 C6 C5 -0.4(3) . . . . ?
C8 C7 C6 N2 0.3(5) . . . . ?
C8 C7 C6 C5 179.8(3) . . . . ?
N1 C5 C6 N2 8.0(4) . . . . ?
C4 C5 C6 N2 -170.0(3) . . . . ?
N1 C5 C6 C7 -171.5(3) . . . . ?
C4 C5 C6 C7 10.4(5) . . . . ?
C6 N2 C10 C9 1.9(5) . . . . ?
NI1 N2 C10 C9 -178.8(3) . . . . ?
C8 C9 C10 N2 -1.1(5) . . . . ?
C15 N3 C11 C12 0.9(5) . . . . ?
NI1 N3 C11 C12 -173.6(3) . . . . ?
N3 C11 C12 C13 0.4(6) . . . . ?
C11 C12 C13 C14 -1.2(5) . . . . ?
C12 C13 C14 C15 0.6(5) . . . . ?
C11 N3 C15 C14 -1.5(4) . . . . ?
NI1 N3 C15 C14 173.6(2) . . . . ?
C11 N3 C15 C16 179.8(3) . . . . ?
NI1 N3 C15 C16 -5.0(3) . . . . ?
C13 C14 C15 N3 0.8(5) . . . . ?
C13 C14 C15 C16 179.4(3) . . . . ?
C20 N4 C16 C17 -1.2(4) . . . . ?
NI1 N4 C16 C17 174.5(2) . . . . ?
C20 N4 C16 C15 179.2(3) . . . . ?
NI1 N4 C16 C15 -5.2(3) . . . . ?
N3 C15 C16 N4 6.8(4) . . . . ?
C14 C15 C16 N4 -171.8(3) . . . . ?
N3 C15 C16 C17 -172.8(3) . . . . ?
C14 C15 C16 C17 8.5(5) . . . . ?
N4 C16 C17 C18 -0.1(5) . . . . ?
C15 C16 C17 C18 179.4(3) . . . . ?
C16 C17 C18 C19 1.4(5) . . . . ?
C17 C18 C19 C20 -1.3(5) . . . . ?
C16 N4 C20 C19 1.3(5) . . . . ?
NI1 N4 C20 C19 -173.8(3) . . . . ?
C18 C19 C20 N4 -0.1(5) . . . . ?

_refine_diff_density_max         0.410
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.095



####################################################################### 
# 
# 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_BTCB24_S_B_Ag_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2261475'
loop_
_audit_author_name
_audit_author_address
'Barbara Tirloni'
;Universidade Federal de Santa Maria
Brazil
;
_audit_update_record             
;
2023-05-08 deposited with the CCDC.	2025-06-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H32 Br4 N8 Ni2 O4 Se2'
_chemical_formula_sum            'C48 H32 Br4 N8 Ni2 O4 Se2'
_chemical_formula_weight         1379.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.1811 1.6452 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3147 0.7232 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se 0.2367 1.4831 '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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.5766(4)
_cell_length_b                   16.8520(6)
_cell_length_c                   26.1453(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4660.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9796
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      22.03

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.967
_exptl_crystal_F_000             2688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.068
_exptl_absorpt_coefficient_mu    3.120
_shelx_estimated_absorpt_T_min   0.547
_shelx_estimated_absorpt_T_max   0.816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6349
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_process_details   
; SADABS (version 2014/5; Bruker, 2014) was used to perform the
multi-scan absorption correction.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.56086
_diffrn_radiation_type           AgK\a
_diffrn_source                   'microfocus X ray tube'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            139739
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0810
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.004
_diffrn_reflns_theta_max         23.643
_diffrn_reflns_theta_full        19.665
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7125
_reflns_number_gt                5217
_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_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond (version 3.2i)'
_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)+(0.0188P)²+4.9782P] 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         7125
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0682
_refine_ls_wR_factor_gt          0.0607
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
SE1 Se 0.32641(3) 0.20445(2) 0.35878(2) 0.04193(7) Uani 1 1 d . . . . .
C1 C 0.8148(3) 0.18337(16) 0.31301(11) 0.0444(6) Uani 1 1 d . . . . .
H1 H 0.793749 0.208985 0.282687 0.053 Uiso 1 1 calc R U . . .
N1 N 0.6187(2) 0.23884(12) 0.43914(8) 0.0353(5) Uani 1 1 d . . . . .
NI1 Ni 0.60740(3) 0.28457(2) 0.36511(2) 0.03102(7) Uani 1 1 d . . . . .
O1 O 0.47734(17) 0.19577(10) 0.34377(8) 0.0442(4) Uani 1 1 d . . . . .
O2 O 0.2490(3) 0.1720(2) 0.31024(10) 0.0892(9) Uani 1 1 d . . . . .
BR2 Br 0.42967(2) 0.38329(2) 0.38146(2) 0.04034(7) Uani 1 1 d . . . . .
N2 N 0.7505(2) 0.20099(11) 0.35504(8) 0.0339(4) Uani 1 1 d . . . . .
C2 C 0.9130(3) 0.12792(18) 0.31241(13) 0.0544(8) Uani 1 1 d . . . . .
H2 H 0.957256 0.118124 0.282340 0.065 Uiso 1 1 calc R U . . .
C3 C 0.9435(3) 0.08818(17) 0.35621(12) 0.0499(7) Uani 1 1 d . . . . .
H3 H 1.009305 0.051550 0.356292 0.060 Uiso 1 1 calc R U . . .
N3 N 0.6227(2) 0.32866(12) 0.29145(8) 0.0362(5) Uani 1 1 d . . . . .
N4 N 0.7415(2) 0.37410(12) 0.37697(8) 0.0363(5) Uani 1 1 d . . . . .
C4 C 0.8747(2) 0.10315(15) 0.40114(11) 0.0387(6) Uani 1 1 d . . . . .
C7 C 0.7287(2) 0.13876(15) 0.48913(10) 0.0381(6) Uani 1 1 d . . . . .
C6 C 0.8235(3) 0.07781(16) 0.48981(11) 0.0448(7) Uani 1 1 d . . . . .
H6 H 0.836431 0.048785 0.519614 0.054 Uiso 1 1 calc R U . . .
C5 C 0.8941(3) 0.06174(16) 0.44822(12) 0.0467(7) Uani 1 1 d . . . . .
H5 H 0.956634 0.023043 0.450162 0.056 Uiso 1 1 calc R U . . .
C9 C 0.5695(3) 0.21993(19) 0.52764(11) 0.0518(7) Uani 1 1 d . . . . .
H9 H 0.522030 0.235408 0.555868 0.062 Uiso 1 1 calc R U . . .
C8 C 0.6559(3) 0.16027(18) 0.53186(11) 0.0489(7) Uani 1 1 d . . . . .
H8 H 0.666620 0.133982 0.562841 0.059 Uiso 1 1 calc R U . . .
C10 C 0.5529(3) 0.25771(17) 0.48040(11) 0.0471(7) Uani 1 1 d . . . . .
H10 H 0.492901 0.297871 0.477928 0.057 Uiso 1 1 calc R U . . .
C11 C 0.7070(2) 0.17997(14) 0.44327(9) 0.0323(5) Uani 1 1 d . . . . .
C12 C 0.7792(2) 0.16115(13) 0.39864(10) 0.0318(5) Uani 1 1 d . . . . .
C13 C 0.5618(3) 0.30573(18) 0.24967(11) 0.0474(7) Uani 1 1 d . . . . .
H13 H 0.507641 0.262349 0.251671 0.057 Uiso 1 1 calc R U . . .
C14 C 0.5759(3) 0.3444(2) 0.20271(12) 0.0571(8) Uani 1 1 d . . . . .
H14 H 0.531820 0.326665 0.174128 0.069 Uiso 1 1 calc R U . . .
C15 C 0.6549(3) 0.4082(2) 0.19901(12) 0.0601(9) Uani 1 1 d . . . . .
H15 H 0.664581 0.434312 0.167909 0.072 Uiso 1 1 calc R U . . .
C16 C 0.7209(3) 0.43419(18) 0.24212(12) 0.0503(7) Uani 1 1 d . . . . .
C17 C 0.8052(4) 0.5009(2) 0.24266(16) 0.0691(11) Uani 1 1 d . . . . .
H17 H 0.818972 0.529017 0.212583 0.083 Uiso 1 1 calc R U . . .
C18 C 0.8648(4) 0.52359(19) 0.28578(17) 0.0683(11) Uani 1 1 d . . . . .
H18 H 0.918290 0.567364 0.284973 0.082 Uiso 1 1 calc R U . . .
C19 C 0.8473(3) 0.48168(16) 0.33266(13) 0.0496(7) Uani 1 1 d . . . . .
C20 C 0.9074(3) 0.50243(19) 0.37822(16) 0.0609(9) Uani 1 1 d . . . . .
H20 H 0.962323 0.545506 0.379121 0.073 Uiso 1 1 calc R U . . .
C21 C 0.8853(3) 0.4592(2) 0.42150(15) 0.0597(9) Uani 1 1 d . . . . .
H21 H 0.926292 0.471990 0.451874 0.072 Uiso 1 1 calc R U . . .
C22 C 0.8004(3) 0.39548(17) 0.41976(12) 0.0473(7) Uani 1 1 d . . . . .
H22 H 0.784684 0.367090 0.449593 0.057 Uiso 1 1 calc R U . . .
C23 C 0.7648(2) 0.41631(14) 0.33399(11) 0.0376(6) Uani 1 1 d . . . . .
C24 C 0.7013(2) 0.39238(14) 0.28822(10) 0.0370(6) Uani 1 1 d . . . . .
BR1A Br 0.2900(4) 0.0850(3) 0.4194(3) 0.0678(10) Uani 0.48(2) 1 d . . P A 1
BR1B Br 0.3053(6) 0.1013(6) 0.4309(3) 0.0834(10) Uani 0.52(2) 1 d . . P A 2


_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
SE1 O2 1.606(3) . ?
SE1 O1 1.6504(18) . ?
SE1 BR1B 2.574(4) . ?
SE1 BR1A 2.590(4) . ?
C1 N2 1.326(3) . ?
C1 C2 1.397(4) . ?
C1 H1 0.9300 . ?
N1 C10 1.323(3) . ?
N1 C11 1.367(3) . ?
N1 NI1 2.087(2) . ?
NI1 N3 2.071(2) . ?
NI1 N2 2.084(2) . ?
NI1 N4 2.094(2) . ?
NI1 O1 2.1078(18) . ?
NI1 BR2 2.5464(4) . ?
N2 C12 1.357(3) . ?
C2 C3 1.365(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.405(4) . ?
C3 H3 0.9300 . ?
N3 C13 1.326(4) . ?
N3 C24 1.361(3) . ?
N4 C22 1.330(3) . ?
N4 C23 1.353(3) . ?
C4 C12 1.407(3) . ?
C4 C5 1.430(4) . ?
C7 C8 1.404(4) . ?
C7 C11 1.405(3) . ?
C7 C6 1.435(4) . ?
C6 C5 1.347(4) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C9 C8 1.363(4) . ?
C9 C10 1.401(4) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.430(3) . ?
C13 C14 1.398(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.365(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.397(5) . ?
C15 H15 0.9300 . ?
C16 C24 1.412(4) . ?
C16 C17 1.434(5) . ?
C17 C18 1.347(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.427(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.395(5) . ?
C19 C23 1.405(4) . ?
C20 C21 1.366(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.400(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.431(4) . ?

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
O2 SE1 O1 105.94(13) . . ?
O2 SE1 BR1B 107.7(3) . . ?
O1 SE1 BR1B 101.43(13) . . ?
O2 SE1 BR1A 98.2(2) . . ?
O1 SE1 BR1A 102.71(10) . . ?
N2 C1 C2 122.7(3) . . ?
N2 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C10 N1 C11 118.0(2) . . ?
C10 N1 NI1 129.61(18) . . ?
C11 N1 NI1 112.37(16) . . ?
N3 NI1 N2 93.92(8) . . ?
N3 NI1 N1 172.22(8) . . ?
N2 NI1 N1 79.98(8) . . ?
N3 NI1 N4 80.00(8) . . ?
N2 NI1 N4 90.78(8) . . ?
N1 NI1 N4 95.16(8) . . ?
N3 NI1 O1 93.41(8) . . ?
N2 NI1 O1 87.75(8) . . ?
N1 NI1 O1 91.19(8) . . ?
N4 NI1 O1 173.14(8) . . ?
N3 NI1 BR2 88.81(6) . . ?
N2 NI1 BR2 177.21(6) . . ?
N1 NI1 BR2 97.35(6) . . ?
N4 NI1 BR2 90.26(6) . . ?
O1 NI1 BR2 91.52(5) . . ?
SE1 O1 NI1 120.35(10) . . ?
C1 N2 C12 118.1(2) . . ?
C1 N2 NI1 128.96(18) . . ?
C12 N2 NI1 112.97(16) . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C13 N3 C24 118.4(2) . . ?
C13 N3 NI1 128.6(2) . . ?
C24 N3 NI1 112.87(17) . . ?
C22 N4 C23 118.1(2) . . ?
C22 N4 NI1 129.57(19) . . ?
C23 N4 NI1 112.28(17) . . ?
C3 C4 C12 117.2(2) . . ?
C3 C4 C5 123.9(2) . . ?
C12 C4 C5 118.8(2) . . ?
C8 C7 C11 117.5(2) . . ?
C8 C7 C6 123.9(3) . . ?
C11 C7 C6 118.6(2) . . ?
C5 C6 C7 121.4(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C8 C9 C10 119.4(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C9 C8 C7 119.6(3) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
N1 C10 C9 123.0(3) . . ?
N1 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
N1 C11 C7 122.6(2) . . ?
N1 C11 C12 117.5(2) . . ?
C7 C11 C12 120.0(2) . . ?
N2 C12 C4 122.9(2) . . ?
N2 C12 C11 117.2(2) . . ?
C4 C12 C11 120.0(2) . . ?
N3 C13 C14 122.4(3) . . ?
N3 C13 H13 118.8 . . ?
C14 C13 H13 118.8 . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C24 117.3(3) . . ?
C15 C16 C17 124.4(3) . . ?
C24 C16 C17 118.3(3) . . ?
C18 C17 C16 121.4(3) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 121.2(3) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C20 C19 C23 117.3(3) . . ?
C20 C19 C18 123.4(3) . . ?
C23 C19 C18 119.3(3) . . ?
C21 C20 C19 119.7(3) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 119.5(3) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
N4 C22 C21 122.4(3) . . ?
N4 C22 H22 118.8 . . ?
C21 C22 H22 118.8 . . ?
N4 C23 C19 123.1(3) . . ?
N4 C23 C24 117.5(2) . . ?
C19 C23 C24 119.5(3) . . ?
N3 C24 C16 122.5(3) . . ?
N3 C24 C23 117.2(2) . . ?
C16 C24 C23 120.3(3) . . ?

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
O2 SE1 O1 NI1 141.01(15) . . . . ?
BR1Bb SE1 O1 NI1 -106.6(3) . . . . ?
BR1Aa SE1 O1 NI1 -116.5(2) . . . . ?
C2 C1 N2 C12 -2.3(4) . . . . ?
C2 C1 N2 NI1 177.0(2) . . . . ?
N2 C1 C2 C3 1.6(5) . . . . ?
C1 C2 C3 C4 0.7(5) . . . . ?
C2 C3 C4 C12 -2.0(4) . . . . ?
C2 C3 C4 C5 176.4(3) . . . . ?
C8 C7 C6 C5 -177.3(3) . . . . ?
C11 C7 C6 C5 2.4(4) . . . . ?
C7 C6 C5 C4 -2.0(4) . . . . ?
C3 C4 C5 C6 -178.8(3) . . . . ?
C12 C4 C5 C6 -0.5(4) . . . . ?
C10 C9 C8 C7 1.3(5) . . . . ?
C11 C7 C8 C9 -0.8(4) . . . . ?
C6 C7 C8 C9 178.9(3) . . . . ?
C11 N1 C10 C9 -0.3(4) . . . . ?
NI1 N1 C10 C9 178.4(2) . . . . ?
C8 C9 C10 N1 -0.8(5) . . . . ?
C10 N1 C11 C7 0.8(4) . . . . ?
NI1 N1 C11 C7 -178.11(19) . . . . ?
C10 N1 C11 C12 -178.9(2) . . . . ?
NI1 N1 C11 C12 2.2(3) . . . . ?
C8 C7 C11 N1 -0.2(4) . . . . ?
C6 C7 C11 N1 180.0(2) . . . . ?
C8 C7 C11 C12 179.4(2) . . . . ?
C6 C7 C11 C12 -0.4(4) . . . . ?
C1 N2 C12 C4 0.9(4) . . . . ?
NI1 N2 C12 C4 -178.60(19) . . . . ?
C1 N2 C12 C11 -178.8(2) . . . . ?
NI1 N2 C12 C11 1.7(3) . . . . ?
C3 C4 C12 N2 1.3(4) . . . . ?
C5 C4 C12 N2 -177.2(2) . . . . ?
C3 C4 C12 C11 -179.1(2) . . . . ?
C5 C4 C12 C11 2.5(4) . . . . ?
N1 C11 C12 N2 -2.7(3) . . . . ?
C7 C11 C12 N2 177.6(2) . . . . ?
N1 C11 C12 C4 177.6(2) . . . . ?
C7 C11 C12 C4 -2.1(4) . . . . ?
C24 N3 C13 C14 0.3(4) . . . . ?
NI1 N3 C13 C14 176.0(2) . . . . ?
N3 C13 C14 C15 -0.1(5) . . . . ?
C13 C14 C15 C16 0.2(5) . . . . ?
C14 C15 C16 C24 -0.5(4) . . . . ?
C14 C15 C16 C17 -179.4(3) . . . . ?
C15 C16 C17 C18 179.0(3) . . . . ?
C24 C16 C17 C18 0.1(5) . . . . ?
C16 C17 C18 C19 0.6(5) . . . . ?
C17 C18 C19 C20 179.5(3) . . . . ?
C17 C18 C19 C23 -1.0(5) . . . . ?
C23 C19 C20 C21 0.4(4) . . . . ?
C18 C19 C20 C21 179.9(3) . . . . ?
C19 C20 C21 C22 -1.3(5) . . . . ?
C23 N4 C22 C21 -0.4(4) . . . . ?
NI1 N4 C22 C21 -177.7(2) . . . . ?
C20 C21 C22 N4 1.3(5) . . . . ?
C22 N4 C23 C19 -0.5(4) . . . . ?
NI1 N4 C23 C19 177.3(2) . . . . ?
C22 N4 C23 C24 179.7(2) . . . . ?
NI1 N4 C23 C24 -2.6(3) . . . . ?
C20 C19 C23 N4 0.5(4) . . . . ?
C18 C19 C23 N4 -179.0(3) . . . . ?
C20 C19 C23 C24 -179.7(2) . . . . ?
C18 C19 C23 C24 0.8(4) . . . . ?
C13 N3 C24 C16 -0.6(4) . . . . ?
NI1 N3 C24 C16 -176.9(2) . . . . ?
C13 N3 C24 C23 179.4(2) . . . . ?
NI1 N3 C24 C23 3.1(3) . . . . ?
C15 C16 C24 N3 0.7(4) . . . . ?
C17 C16 C24 N3 179.7(3) . . . . ?
C15 C16 C24 C23 -179.3(2) . . . . ?
C17 C16 C24 C23 -0.3(4) . . . . ?
N4 C23 C24 N3 -0.3(3) . . . . ?
C19 C23 C24 N3 179.9(2) . . . . ?
N4 C23 C24 C16 179.7(2) . . . . ?
C19 C23 C24 C16 -0.2(4) . . . . ?

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.078



