# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1014259'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2021-03-14 deposited with the CCDC.	2021-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H7 N2 Se, Cl'
_chemical_formula_sum            'C7 H7 Cl N2 Se'
_chemical_formula_weight         233.56

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.0750(4)
_cell_length_b                   9.3531(5)
_cell_length_c                   12.5898(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.1730(10)
_cell_angle_gamma                90
_cell_volume                     822.45(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6317
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      32.60

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.886
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    4.821
_shelx_estimated_absorpt_T_min   0.379
_shelx_estimated_absorpt_T_max   0.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.315
_exptl_absorpt_correction_T_max  0.722
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12580
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.725
_diffrn_reflns_theta_max         32.604
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3005
_reflns_number_gt                2688
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0294P)²+0.1894P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3005
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0232
_refine_ls_wR_factor_ref         0.0591
_refine_ls_wR_factor_gt          0.0572
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.20826(2) 0.44431(2) 0.41459(2) 0.01848(5) Uani 1 1 d . . . . .
Cl1 Cl 0.41177(5) 0.18071(4) 0.34852(3) 0.02341(8) Uani 1 1 d . . . . .
N1 N 0.10637(18) 0.61179(14) 0.45849(10) 0.0212(2) Uani 1 1 d . . . . .
N2 N 0.36590(17) 0.69710(13) 0.38842(9) 0.0179(2) Uani 1 1 d . . . . .
C1 C 0.2028(2) 0.72185(15) 0.43850(12) 0.0198(2) Uani 1 1 d . . . . .
C2 C 0.3952(2) 0.55663(14) 0.36642(11) 0.0183(2) Uani 1 1 d . . . . .
C3 C 0.5510(2) 0.51739(16) 0.31691(12) 0.0211(3) Uani 1 1 d . . . . .
H3 H 0.5724 0.4200 0.3011 0.025 Uiso 1 1 calc R U . . .
C4 C 0.6733(2) 0.62265(17) 0.29134(13) 0.0247(3) Uani 1 1 d . . . . .
H4 H 0.7802 0.5982 0.2579 0.030 Uiso 1 1 calc R U . . .
C5 C 0.6384(2) 0.76596(18) 0.31511(13) 0.0262(3) Uani 1 1 d . . . . .
H5 H 0.7222 0.8384 0.2974 0.031 Uiso 1 1 calc R U . . .
C6 C 0.4858(2) 0.80264(16) 0.36322(12) 0.0223(3) Uani 1 1 d . . . . .
H6 H 0.4629 0.8998 0.3791 0.027 Uiso 1 1 calc R U . . .
C7 C 0.1519(2) 0.87099(16) 0.46517(14) 0.0252(3) Uani 1 1 d . . . . .
H7A H 0.0336 0.8700 0.4964 0.038 Uiso 1 1 calc R U . . .
H7B H 0.1329 0.9290 0.3995 0.038 Uiso 1 1 calc R U . . .
H7C H 0.2557 0.9119 0.5171 0.038 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 N1 1.8455(13) . ?
Se1 C2 1.8646(14) . ?
N1 C1 1.2820(19) . ?
N2 C2 1.3654(18) . ?
N2 C6 1.3714(18) . ?
N2 C1 1.4192(18) . ?
C1 C7 1.492(2) . ?
C2 C3 1.399(2) . ?
C3 C4 1.382(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.404(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.363(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

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 Se1 C2 87.16(6) . . ?
C1 N1 Se1 112.16(10) . . ?
C2 N2 C6 121.74(12) . . ?
C2 N2 C1 114.05(12) . . ?
C6 N2 C1 124.21(12) . . ?
N1 C1 N2 116.88(13) . . ?
N1 C1 C7 123.46(14) . . ?
N2 C1 C7 119.66(13) . . ?
N2 C2 C3 119.92(13) . . ?
N2 C2 Se1 109.73(10) . . ?
C3 C2 Se1 130.34(11) . . ?
C4 C3 C2 118.94(14) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 119.49(14) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.93(14) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 N2 118.99(14) . . ?
C5 C6 H6 120.5 . . ?
N2 C6 H6 120.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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 Se1 N1 C1 -0.42(11) . . . . ?
Se1 N1 C1 N2 -0.30(17) . . . . ?
Se1 N1 C1 C7 179.76(12) . . . . ?
C2 N2 C1 N1 1.19(19) . . . . ?
C6 N2 C1 N1 -178.92(14) . . . . ?
C2 N2 C1 C7 -178.87(13) . . . . ?
C6 N2 C1 C7 1.0(2) . . . . ?
C6 N2 C2 C3 0.0(2) . . . . ?
C1 N2 C2 C3 179.92(13) . . . . ?
C6 N2 C2 Se1 178.68(11) . . . . ?
C1 N2 C2 Se1 -1.42(14) . . . . ?
N1 Se1 C2 N2 1.03(10) . . . . ?
N1 Se1 C2 C3 179.51(15) . . . . ?
N2 C2 C3 C4 0.2(2) . . . . ?
Se1 C2 C3 C4 -178.19(12) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C4 C5 C6 N2 0.0(2) . . . . ?
C2 N2 C6 C5 -0.1(2) . . . . ?
C1 N2 C6 C5 180.00(14) . . . . ?

_refine_diff_density_max         0.502
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.122

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1014261'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2021-03-14 deposited with the CCDC.	2021-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H7 N2 Se, Br'
_chemical_formula_sum            'C7 H7 Br N2 Se'
_chemical_formula_weight         278.02

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'
Se Se -0.0929 2.2259 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.1030(5)
_cell_length_b                   9.6595(7)
_cell_length_c                   12.7813(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.099(2)
_cell_angle_gamma                90
_cell_volume                     868.20(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3662
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      31.80

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.127
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    8.862
_shelx_estimated_absorpt_T_min   0.215
_shelx_estimated_absorpt_T_max   0.350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.128
_exptl_absorpt_correction_T_max  0.242
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13339
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.653
_diffrn_reflns_theta_max         32.603
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3178
_reflns_number_gt                2587
_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       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0338P)²+0.1402P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3178
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0755
_refine_ls_wR_factor_gt          0.0706
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.41656(4) 0.81687(3) 0.35389(2) 0.02647(7) Uani 1 1 d . . . . .
Se1 Se 0.20890(3) 0.54720(2) 0.41820(2) 0.02200(7) Uani 1 1 d . . . . .
N1 N 0.3563(3) 0.2998(2) 0.38690(17) 0.0225(4) Uani 1 1 d . . . . .
N2 N 0.1005(3) 0.3855(2) 0.45974(17) 0.0246(4) Uani 1 1 d . . . . .
C1 C 0.3906(4) 0.4365(3) 0.36728(19) 0.0222(4) Uani 1 1 d . . . . .
C2 C 0.5470(4) 0.4720(3) 0.3178(2) 0.0258(5) Uani 1 1 d . . . . .
H2 H 0.5733 0.5662 0.3041 0.031 Uiso 1 1 calc R U . . .
C3 C 0.6636(4) 0.3673(3) 0.2890(2) 0.0294(5) Uani 1 1 d . . . . .
H3 H 0.7706 0.3894 0.2552 0.035 Uiso 1 1 calc R U . . .
C4 C 0.6228(4) 0.2297(3) 0.3099(2) 0.0320(6) Uani 1 1 d . . . . .
H4 H 0.7023 0.1583 0.2896 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4707(4) 0.1961(3) 0.3589(2) 0.0280(5) Uani 1 1 d . . . . .
H5 H 0.4444 0.1022 0.3735 0.034 Uiso 1 1 calc R U . . .
C6 C 0.1923(3) 0.2777(3) 0.43692(19) 0.0227(4) Uani 1 1 d . . . . .
C7 C 0.1347(4) 0.1347(3) 0.4602(2) 0.0303(5) Uani 1 1 d . . . . .
H7A H 0.0181 0.1376 0.4931 0.046 Uiso 1 1 calc R U . . .
H7B H 0.2363 0.0905 0.5087 0.046 Uiso 1 1 calc R U . . .
H7C H 0.1115 0.0815 0.3944 0.046 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 N2 1.852(2) . ?
Se1 C1 1.862(2) . ?
N1 C5 1.369(3) . ?
N1 C1 1.372(3) . ?
N1 C6 1.422(3) . ?
N2 C6 1.284(3) . ?
C1 C2 1.396(3) . ?
C2 C3 1.389(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.363(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.483(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

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
N2 Se1 C1 87.29(10) . . ?
C5 N1 C1 122.0(2) . . ?
C5 N1 C6 124.1(2) . . ?
C1 N1 C6 113.9(2) . . ?
C6 N2 Se1 111.94(17) . . ?
N1 C1 C2 119.5(2) . . ?
N1 C1 Se1 109.82(17) . . ?
C2 C1 Se1 130.71(19) . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 N1 118.9(2) . . ?
C4 C5 H5 120.5 . . ?
N1 C5 H5 120.5 . . ?
N2 C6 N1 117.1(2) . . ?
N2 C6 C7 123.1(2) . . ?
N1 C6 C7 119.8(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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
C1 Se1 N2 C6 0.19(19) . . . . ?
C5 N1 C1 C2 -0.3(4) . . . . ?
C6 N1 C1 C2 -179.6(2) . . . . ?
C5 N1 C1 Se1 -179.03(19) . . . . ?
C6 N1 C1 Se1 1.7(3) . . . . ?
N2 Se1 C1 N1 -1.07(17) . . . . ?
N2 Se1 C1 C2 -179.6(3) . . . . ?
N1 C1 C2 C3 0.5(4) . . . . ?
Se1 C1 C2 C3 178.8(2) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 N1 0.6(4) . . . . ?
C1 N1 C5 C4 -0.2(4) . . . . ?
C6 N1 C5 C4 179.0(2) . . . . ?
Se1 N2 C6 N1 0.7(3) . . . . ?
Se1 N2 C6 C7 -179.2(2) . . . . ?
C5 N1 C6 N2 179.1(2) . . . . ?
C1 N1 C6 N2 -1.7(3) . . . . ?
C5 N1 C6 C7 -1.0(4) . . . . ?
C1 N1 C6 C7 178.3(2) . . . . ?

_refine_diff_density_max         0.863
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.125

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 2070444'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2021-03-14 deposited with the CCDC.	2021-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 Br N2 Se, Br'
_chemical_formula_sum            'C12 H8 Br2 N2 Se'
_chemical_formula_weight         418.96

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   29.431(2)
_cell_length_b                   7.1286(5)
_cell_length_c                   13.0733(9)
_cell_angle_alpha                90
_cell_angle_beta                 115.186(2)
_cell_angle_gamma                90
_cell_volume                     2482.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4536
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      31.09

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.242
_exptl_crystal_F_000             1584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    9.441
_shelx_estimated_absorpt_T_min   0.210
_shelx_estimated_absorpt_T_max   0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.112
_exptl_absorpt_correction_T_max  0.743
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27223
_diffrn_reflns_av_unetI/netI     0.0772
_diffrn_reflns_av_R_equivalents  0.1193
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.059
_diffrn_reflns_theta_max         32.612
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4533
_reflns_number_gt                3039
_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 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'

_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)+(0.0318P)²+1.7141P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4533
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.0962
_refine_ls_wR_factor_gt          0.0795
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
Br1 Br 0.77615(2) 0.50480(6) 1.17007(4) 0.02513(12) Uani 1 1 d . . . . .
Br2 Br 0.40928(2) 0.18946(6) 0.36162(3) 0.01808(10) Uani 1 1 d . . . . .
Se1 Se 0.49609(2) 0.27838(6) 0.59712(3) 0.01576(10) Uani 1 1 d . . . . .
N2 N 0.54828(14) 0.3240(5) 0.7353(3) 0.0173(7) Uani 1 1 d . . . . .
C3 C 0.59093(16) 0.3257(5) 0.7307(3) 0.0152(8) Uani 1 1 d . . . . .
N4 N 0.59063(14) 0.2901(4) 0.6224(3) 0.0147(7) Uani 1 1 d . . . . .
C5 C 0.54365(17) 0.2630(5) 0.5388(3) 0.0168(8) Uani 1 1 d . . . . .
C6 C 0.53744(17) 0.2285(6) 0.4287(3) 0.0183(8) Uani 1 1 d . . . . .
H6 H 0.5048 0.2150 0.3692 0.022 Uiso 1 1 calc R U . . .
C7 C 0.57889(18) 0.2142(6) 0.4073(4) 0.0214(9) Uani 1 1 d . . . . .
H7 H 0.5751 0.1913 0.3325 0.026 Uiso 1 1 calc R U . . .
C8 C 0.62716(17) 0.2335(6) 0.4958(3) 0.0178(8) Uani 1 1 d . . . . .
H8 H 0.6560 0.2206 0.4812 0.021 Uiso 1 1 calc R U . . .
C9 C 0.63253(16) 0.2705(5) 0.6022(3) 0.0173(8) Uani 1 1 d . . . . .
H9 H 0.6651 0.2827 0.6623 0.021 Uiso 1 1 calc R U . . .
C10 C 0.63836(16) 0.3607(5) 0.8330(3) 0.0159(8) Uani 1 1 d . . . . .
C11 C 0.67537(17) 0.4823(5) 0.8331(3) 0.0178(8) Uani 1 1 d . . . . .
H11 H 0.6720 0.5403 0.7648 0.021 Uiso 1 1 calc R U . . .
C12 C 0.71732(17) 0.5185(5) 0.9336(3) 0.0183(8) Uani 1 1 d . . . . .
H12 H 0.7433 0.5985 0.9341 0.022 Uiso 1 1 calc R U . . .
C13 C 0.72081(17) 0.4370(6) 1.0324(3) 0.0198(9) Uani 1 1 d . . . . .
C14 C 0.68436(17) 0.3175(6) 1.0344(3) 0.0190(9) Uani 1 1 d . . . . .
H14 H 0.6874 0.2634 1.1034 0.023 Uiso 1 1 calc R U . . .
C15 C 0.64301(16) 0.2778(6) 0.9333(3) 0.0181(8) Uani 1 1 d . . . . .
H15 H 0.6179 0.1937 0.9329 0.022 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 C13 1.905(4) . ?
Se1 N2 1.835(3) . ?
Se1 C5 1.860(4) . ?
N2 C3 1.282(6) . ?
C3 N4 1.435(5) . ?
C3 C10 1.487(6) . ?
N4 C5 1.363(5) . ?
N4 C9 1.374(5) . ?
C5 C6 1.393(6) . ?
C6 C7 1.367(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.406(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.357(6) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C15 1.391(6) . ?
C10 C11 1.392(6) . ?
C11 C12 1.392(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(6) . ?
C14 C15 1.393(6) . ?
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
N2 Se1 C5 87.31(17) . . ?
C3 N2 Se1 112.5(3) . . ?
N2 C3 N4 116.7(4) . . ?
N2 C3 C10 121.5(4) . . ?
N4 C3 C10 121.8(4) . . ?
C5 N4 C9 121.2(3) . . ?
C5 N4 C3 113.2(4) . . ?
C9 N4 C3 125.4(4) . . ?
N4 C5 C6 119.7(4) . . ?
N4 C5 Se1 110.3(3) . . ?
C6 C5 Se1 130.0(3) . . ?
C7 C6 C5 119.3(4) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C8 120.1(4) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 119.9(4) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 N4 119.6(4) . . ?
C8 C9 H9 120.2 . . ?
N4 C9 H9 120.2 . . ?
C15 C10 C11 120.1(4) . . ?
C15 C10 C3 117.0(4) . . ?
C11 C10 C3 122.7(4) . . ?
C10 C11 C12 119.7(4) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 119.2(4) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 121.9(4) . . ?
C14 C13 Br1 119.9(3) . . ?
C12 C13 Br1 118.1(3) . . ?
C13 C14 C15 118.8(4) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C10 C15 C14 120.2(4) . . ?
C10 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?

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
C5 Se1 N2 C3 0.3(3) . . . . ?
Se1 N2 C3 N4 -0.9(4) . . . . ?
Se1 N2 C3 C10 179.8(3) . . . . ?
N2 C3 N4 C5 1.2(5) . . . . ?
C10 C3 N4 C5 -179.4(3) . . . . ?
N2 C3 N4 C9 -174.2(4) . . . . ?
C10 C3 N4 C9 5.1(6) . . . . ?
C9 N4 C5 C6 -4.9(6) . . . . ?
C3 N4 C5 C6 179.5(3) . . . . ?
C9 N4 C5 Se1 174.7(3) . . . . ?
C3 N4 C5 Se1 -0.9(4) . . . . ?
N2 Se1 C5 N4 0.4(3) . . . . ?
N2 Se1 C5 C6 179.9(4) . . . . ?
N4 C5 C6 C7 2.8(6) . . . . ?
Se1 C5 C6 C7 -176.7(3) . . . . ?
C5 C6 C7 C8 0.3(6) . . . . ?
C6 C7 C8 C9 -1.5(6) . . . . ?
C7 C8 C9 N4 -0.4(6) . . . . ?
C5 N4 C9 C8 3.7(6) . . . . ?
C3 N4 C9 C8 178.8(4) . . . . ?
N2 C3 C10 C15 40.2(6) . . . . ?
N4 C3 C10 C15 -139.1(4) . . . . ?
N2 C3 C10 C11 -134.8(4) . . . . ?
N4 C3 C10 C11 45.9(6) . . . . ?
C15 C10 C11 C12 0.8(6) . . . . ?
C3 C10 C11 C12 175.6(4) . . . . ?
C10 C11 C12 C13 -1.8(6) . . . . ?
C11 C12 C13 C14 1.3(6) . . . . ?
C11 C12 C13 Br1 -175.3(3) . . . . ?
C12 C13 C14 C15 0.3(6) . . . . ?
Br1 C13 C14 C15 176.8(3) . . . . ?
C11 C10 C15 C14 0.7(6) . . . . ?
C3 C10 C15 C14 -174.3(4) . . . . ?
C13 C14 C15 C10 -1.3(6) . . . . ?

_refine_diff_density_max         0.873
_refine_diff_density_min         -1.227
_refine_diff_density_rms         0.209

_shelxl_version_number           2013-4



