# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2254283'
loop_
_audit_author_name
_audit_author_address
'Alexey Kubasov'
;Kurnakov Institute of General and Inorganic Chemistry
Russia
;
_audit_update_record             
;
2023-04-05 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;
_audit_creation_date             2023-04-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H10 N3 Se, Cl'
_chemical_formula_sum            'C8 H10 Cl N3 Se'
_chemical_formula_weight         262.60
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   7.3227(9)
_cell_length_b                   8.9950(14)
_cell_length_c                   15.321(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.442(6)
_cell_angle_gamma                90
_cell_volume                     981.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4806
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      30.07
_cell_measurement_theta_min      2.86
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.294
_exptl_absorpt_coefficient_mu    4.053
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0599 before and 0.0410 after correction.
The Ratio of minimum to maximum transmission is 0.7869.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5237
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_min         2.264
_diffrn_ambient_temperature      120.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1849
_reflns_number_total             1935
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.241
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1935
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0265
_refine_ls_restrained_S_all      1.241
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+2.3209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0648
_refine_ls_wR_factor_ref         0.0689
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.8558(10)
 0.1442(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Se1 Se 0.71372(6) 0.46833(4) 0.45071(2) 0.01656(11) Uani 1 1 d . . . . .
N1 N 0.6188(5) 0.6210(4) 0.3733(2) 0.0204(7) Uani 1 1 d . . . . .
N2 N 0.7263(4) 0.7479(3) 0.5067(2) 0.0152(6) Uani 1 1 d . . . . .
N3 N 0.5787(5) 0.8812(4) 0.3723(2) 0.0202(7) Uani 1 1 d . . . . .
C1 C 0.7810(5) 0.6109(4) 0.5403(2) 0.0152(7) Uani 1 1 d . . . . .
C2 C 0.8672(5) 0.5946(4) 0.6312(2) 0.0183(8) Uani 1 1 d . . . . .
H2 H 0.905097 0.499135 0.655235 0.022 Uiso 1 1 calc R U . . .
C3 C 0.8966(6) 0.7179(5) 0.6854(3) 0.0217(9) Uani 1 1 d . . . . .
H3 H 0.957192 0.708791 0.747106 0.026 Uiso 1 1 calc R U . . .
C4 C 0.8369(6) 0.8570(4) 0.6491(3) 0.0222(8) Uani 1 1 d . . . . .
H4 H 0.857080 0.942449 0.686563 0.027 Uiso 1 1 calc R U . . .
C5 C 0.7501(6) 0.8717(4) 0.5608(3) 0.0198(8) Uani 1 1 d . . . . .
H5 H 0.706705 0.966110 0.536844 0.024 Uiso 1 1 calc R U . . .
C6 C 0.6414(6) 0.7479(4) 0.4124(2) 0.0185(8) Uani 1 1 d . . . . .
C7 C 0.7179(6) 0.9983(4) 0.3689(3) 0.0258(9) Uani 1 1 d . . . . .
H7A H 0.828691 0.983927 0.418137 0.039 Uiso 1 1 calc R U . . .
H7B H 0.662621 1.095961 0.374695 0.039 Uiso 1 1 calc R U . . .
H7C H 0.754780 0.992766 0.311417 0.039 Uiso 1 1 calc R U . . .
C8 C 0.4465(6) 0.8601(5) 0.2852(3) 0.0251(9) Uani 1 1 d . . . . .
H8A H 0.512504 0.815827 0.242758 0.038 Uiso 1 1 calc R U . . .
H8B H 0.393962 0.956410 0.262171 0.038 Uiso 1 1 calc R U . . .
H8C H 0.344829 0.793826 0.292455 0.038 Uiso 1 1 calc R U . . .
Cl1 Cl 0.88262(15) 0.24025(10) 0.57557(6) 0.0218(2) Uani 1 1 d . . . . .


_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 1.842(3) . ?
Se1 C1 1.860(4) . ?
N1 C6 1.282(5) . ?
N2 C1 1.360(5) . ?
N2 C5 1.374(5) . ?
N2 C6 1.434(5) . ?
N3 C6 1.376(5) . ?
N3 C7 1.475(5) . ?
N3 C8 1.468(5) . ?
C1 C2 1.396(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.372(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.361(6) . ?
C5 H5 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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 C1 87.53(15) . . ?
C6 N1 Se1 112.0(3) . . ?
C1 N2 C5 121.4(3) . . ?
C1 N2 C6 113.7(3) . . ?
C5 N2 C6 124.9(3) . . ?
C6 N3 C7 118.5(3) . . ?
C6 N3 C8 111.9(3) . . ?
C8 N3 C7 112.0(3) . . ?
N2 C1 Se1 109.9(3) . . ?
N2 C1 C2 119.9(3) . . ?
C2 C1 Se1 130.1(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.3(4) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.5(4) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.9(4) . . ?
C5 C4 H4 119.6 . . ?
N2 C5 H5 120.5 . . ?
C4 C5 N2 119.0(4) . . ?
C4 C5 H5 120.5 . . ?
N1 C6 N2 116.7(3) . . ?
N1 C6 N3 125.1(3) . . ?
N3 C6 N2 118.1(3) . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
Se1 N1 C6 N2 -2.4(5) . . . . ?
Se1 N1 C6 N3 -177.6(3) . . . . ?
Se1 C1 C2 C3 -177.6(3) . . . . ?
N1 Se1 C1 N2 1.3(3) . . . . ?
N1 Se1 C1 C2 178.7(4) . . . . ?
N2 C1 C2 C3 -0.4(6) . . . . ?
C1 Se1 N1 C6 0.6(3) . . . . ?
C1 N2 C5 C4 2.5(6) . . . . ?
C1 N2 C6 N1 3.5(5) . . . . ?
C1 N2 C6 N3 179.0(3) . . . . ?
C1 C2 C3 C4 1.1(6) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C3 C4 C5 N2 -1.8(6) . . . . ?
C5 N2 C1 Se1 176.2(3) . . . . ?
C5 N2 C1 C2 -1.5(5) . . . . ?
C5 N2 C6 N1 -175.5(4) . . . . ?
C5 N2 C6 N3 0.1(6) . . . . ?
C6 N2 C1 Se1 -2.8(4) . . . . ?
C6 N2 C1 C2 179.5(3) . . . . ?
C6 N2 C5 C4 -178.5(4) . . . . ?
C7 N3 C6 N1 -120.0(4) . . . . ?
C7 N3 C6 N2 64.9(5) . . . . ?
C8 N3 C6 N1 12.7(6) . . . . ?
C8 N3 C6 N2 -162.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8558(10)
2 0.1442(10)

####################################################################### 
# 
# 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_mo_21kub116_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2254287'
loop_
_audit_author_name
_audit_author_address
'Alexey Kubasov'
;Kurnakov Institute of General and Inorganic Chemistry
Russia
;
_audit_update_record             
;
2023-04-05 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;
_audit_creation_date             2023-04-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H8 N5 Se, Cl, H2 O'
_chemical_formula_sum            'C7 H10 Cl N5 O Se'
_chemical_formula_weight         294.61
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   7.8986(15)
_cell_length_b                   14.662(4)
_cell_length_c                   9.851(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.161(15)
_cell_angle_gamma                90
_cell_volume                     1063.9(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7990
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      33.092
_cell_measurement_theta_min      2.615
_shelx_estimated_absorpt_T_max   0.315
_shelx_estimated_absorpt_T_min   0.211
_exptl_absorpt_coefficient_mu    3.762
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.3370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1109 before and 0.0463 after correction.
The Ratio of minimum to maximum transmission is 0.4514.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.839
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7772
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.152
_diffrn_reflns_theta_min         2.616
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3434
_reflns_number_total             3987
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.549
_refine_diff_density_min         -1.657
_refine_diff_density_rms         0.162
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         3987
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.053
_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)+(0.0513P)²+0.9974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1063
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.c X=CH2 refined with riding coordinates:
 N4(H4A,H4B), N5(H5A,H5B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Se1 Se 0.10411(3) 0.50327(2) 0.21453(2) 0.00945(7) Uani 1 1 d . . . . .
N1 N 0.0679(2) 0.58136(12) 0.34736(19) 0.0111(3) Uani 1 1 d . . . . .
N2 N 0.2694(2) 0.47708(12) 0.4984(2) 0.0096(3) Uani 1 1 d . . . . .
N3 N 0.1808(3) 0.59901(12) 0.60808(19) 0.0112(3) Uani 1 1 d . . . . .
N4 N 0.1307(3) 0.71710(13) 0.7382(2) 0.0161(4) Uani 1 1 d . . . . .
H4A H 0.077672 0.768711 0.745288 0.019 Uiso 1 1 calc R U . . .
H4B H 0.208750 0.691467 0.816639 0.019 Uiso 1 1 calc R U . . .
N5 N -0.0257(3) 0.71764(14) 0.4910(2) 0.0152(4) Uani 1 1 d . . . . .
H5A H -0.052216 0.692775 0.404435 0.018 Uiso 1 1 calc R U . . .
H5B H -0.077557 0.769171 0.500314 0.018 Uiso 1 1 calc R U . . .
C1 C 0.2633(3) 0.43843(13) 0.3711(2) 0.0093(3) Uani 1 1 d . . . . .
C2 C 0.3673(3) 0.36076(14) 0.3740(2) 0.0121(4) Uani 1 1 d . . . . .
H2 H 0.365092 0.333065 0.286194 0.015 Uiso 1 1 calc R U . . .
C3 C 0.4729(3) 0.32540(15) 0.5069(2) 0.0135(4) Uani 1 1 d . . . . .
H3 H 0.546270 0.273365 0.510920 0.016 Uiso 1 1 calc R U . . .
C4 C 0.4736(3) 0.36526(14) 0.6366(2) 0.0139(4) Uani 1 1 d . . . . .
H4 H 0.544518 0.339290 0.727770 0.017 Uiso 1 1 calc R U . . .
C5 C 0.3720(3) 0.44154(14) 0.6313(2) 0.0111(3) Uani 1 1 d . . . . .
H5 H 0.372620 0.469487 0.718474 0.013 Uiso 1 1 calc R U . . .
C6 C 0.1617(3) 0.55906(13) 0.4815(2) 0.0103(3) Uani 1 1 d . . . . .
C7 C 0.0926(3) 0.67739(14) 0.6074(2) 0.0111(3) Uani 1 1 d . . . . .
Cl1 Cl 0.74833(7) 0.60358(3) 0.99889(6) 0.01365(11) Uani 1 1 d . . . . .
O1 O 0.3495(2) 0.61533(11) 0.99675(19) 0.0171(3) Uani 1 1 d G . . . .
H1A H 0.306768 0.560148 0.989972 0.026 Uiso 1 1 d G U . . .
H1B H 0.456529 0.608728 0.991744 0.026 Uiso 1 1 d G 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 1.8370(18) . ?
Se1 C1 1.861(2) . ?
N1 C6 1.302(3) . ?
N2 C1 1.362(3) . ?
N2 C5 1.370(3) . ?
N2 C6 1.447(3) . ?
N3 C6 1.336(3) . ?
N3 C7 1.343(3) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N4 C7 1.345(3) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C7 1.328(3) . ?
C1 C2 1.398(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.374(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.403(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.366(3) . ?
C5 H5 0.9500 . ?
O1 H1A 0.8698 . ?
O1 H1B 0.8698 . ?

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 C1 87.74(9) . . ?
C6 N1 Se1 112.86(14) . . ?
C1 N2 C5 122.28(18) . . ?
C1 N2 C6 114.54(17) . . ?
C5 N2 C6 123.17(17) . . ?
C6 N3 C7 119.16(18) . . ?
H4A N4 H4B 120.0 . . ?
C7 N4 H4A 120.0 . . ?
C7 N4 H4B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C7 N5 H5A 120.0 . . ?
C7 N5 H5B 120.0 . . ?
N2 C1 Se1 109.84(14) . . ?
N2 C1 C2 119.64(18) . . ?
C2 C1 Se1 130.51(15) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.50(19) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
N2 C5 H5 120.5 . . ?
C4 C5 N2 118.99(19) . . ?
C4 C5 H5 120.5 . . ?
N1 C6 N2 114.93(17) . . ?
N1 C6 N3 131.93(19) . . ?
N3 C6 N2 113.12(18) . . ?
N3 C7 N4 115.44(19) . . ?
N5 C7 N3 125.90(19) . . ?
N5 C7 N4 118.7(2) . . ?
H1A O1 H1B 104.5 . . ?

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
Se1 N1 C6 N2 -1.7(2) . . . . ?
Se1 N1 C6 N3 176.58(19) . . . . ?
Se1 C1 C2 C3 -178.91(17) . . . . ?
N1 Se1 C1 N2 1.70(15) . . . . ?
N1 Se1 C1 C2 -179.1(2) . . . . ?
N2 C1 C2 C3 0.2(3) . . . . ?
C1 Se1 N1 C6 0.05(16) . . . . ?
C1 N2 C5 C4 0.8(3) . . . . ?
C1 N2 C6 N1 3.2(3) . . . . ?
C1 N2 C6 N3 -175.41(18) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C3 C4 C5 N2 0.7(3) . . . . ?
C5 N2 C1 Se1 178.05(16) . . . . ?
C5 N2 C1 C2 -1.3(3) . . . . ?
C5 N2 C6 N1 -177.84(19) . . . . ?
C5 N2 C6 N3 3.5(3) . . . . ?
C6 N2 C1 Se1 -3.0(2) . . . . ?
C6 N2 C1 C2 177.67(18) . . . . ?
C6 N2 C5 C4 -178.08(19) . . . . ?
C6 N3 C7 N4 -174.67(19) . . . . ?
C6 N3 C7 N5 5.2(3) . . . . ?
C7 N3 C6 N1 -0.4(3) . . . . ?
C7 N3 C6 N2 177.91(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_21kub154_0m_b
_database_code_depnum_ccdc_archive 'CCDC 2254284'
loop_
_audit_author_name
_audit_author_address
'Alexey Kubasov'
;Kurnakov Institute of General and Inorganic Chemistry
Russia
;
_audit_update_record             
;
2023-04-05 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;
_audit_creation_date             2023-04-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H12 N3 O Se, Cl'
_chemical_formula_sum            'C13 H12 Cl N3 O Se'
_chemical_formula_weight         340.67
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   6.9994(10)
_cell_length_b                   8.8877(10)
_cell_length_c                   20.694(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1287.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5981
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      32.508
_cell_measurement_theta_min      2.497
_shelx_estimated_absorpt_T_max   0.912
_shelx_estimated_absorpt_T_min   0.256
_exptl_absorpt_coefficient_mu    3.118
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.4486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1479 before and 0.0651 after correction.
The Ratio of minimum to maximum transmission is 0.6010.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            6508
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.996
_diffrn_reflns_theta_min         2.494
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.951
_reflns_Friedel_fraction_max     0.941
_reflns_number_gt                3287
_reflns_number_total             3641
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details 
;
 Flack x determined using 1237 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.147(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3641
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.015
_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)+(0.0353P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0858
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C3(H3A), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Se1 Se 0.49454(6) 0.64240(4) 0.46874(2) 0.01393(10) Uani 1 1 d . . . . .
O1 O 0.5686(4) -0.0507(3) 0.73525(14) 0.0176(6) Uani 1 1 d . . . . .
N2 N 0.5717(4) 0.3909(3) 0.40534(15) 0.0109(6) Uani 1 1 d . . . . .
N1 N 0.5116(6) 0.4619(3) 0.51177(15) 0.0148(6) Uani 1 1 d . . . . .
N3 N 0.5687(5) 0.2057(4) 0.48865(16) 0.0136(6) Uani 1 1 d . . . . .
H3 H 0.581688 0.140180 0.457088 0.016 Uiso 1 1 calc R U . . .
C1 C 0.5419(5) 0.5394(4) 0.39179(18) 0.0119(7) Uani 1 1 d . . . . .
C2 C 0.5558(5) 0.5918(4) 0.32846(18) 0.0131(7) Uani 1 1 d . . . . .
H2 H 0.531239 0.694521 0.318866 0.016 Uiso 1 1 calc R U . . .
C3 C 0.6053(6) 0.4936(5) 0.2802(2) 0.0152(8) Uani 1 1 d . . . . .
H3A H 0.613823 0.527523 0.236731 0.018 Uiso 1 1 calc R U . . .
C4 C 0.6434(5) 0.3417(4) 0.29554(19) 0.0148(8) Uani 1 1 d . . . . .
H4 H 0.681157 0.273534 0.262545 0.018 Uiso 1 1 calc R U . . .
C5 C 0.6262(5) 0.2929(5) 0.35767(19) 0.0137(7) Uani 1 1 d . . . . .
H5 H 0.651913 0.190690 0.367964 0.016 Uiso 1 1 calc R U . . .
C6 C 0.5481(5) 0.3534(4) 0.47262(17) 0.0119(7) Uani 1 1 d . . . . .
C7 C 0.5704(5) 0.1509(4) 0.55301(19) 0.0129(7) Uani 1 1 d . . . . .
C8 C 0.6311(5) 0.2347(4) 0.60614(19) 0.0130(7) Uani 1 1 d . . . . .
H8 H 0.672289 0.335645 0.600295 0.016 Uiso 1 1 calc R U . . .
C9 C 0.6319(5) 0.1714(4) 0.66784(19) 0.0131(7) Uani 1 1 d . . . . .
H9 H 0.669575 0.229869 0.704086 0.016 Uiso 1 1 calc R U . . .
C10 C 0.5770(6) 0.0214(4) 0.67605(19) 0.0135(7) Uani 1 1 d . . . . .
C11 C 0.5212(5) -0.0637(4) 0.62273(18) 0.0156(7) Uani 1 1 d . . . . .
H11 H 0.485924 -0.166164 0.628107 0.019 Uiso 1 1 calc R U . . .
C12 C 0.5172(6) 0.0007(4) 0.56227(18) 0.0145(7) Uani 1 1 d . . . . .
H12 H 0.477721 -0.057767 0.526232 0.017 Uiso 1 1 calc R U . . .
C13 C 0.5938(6) 0.0399(5) 0.79169(19) 0.0210(9) Uani 1 1 d . . . . .
H13A H 0.508665 0.127278 0.789503 0.031 Uiso 1 1 calc R U . . .
H13B H 0.726728 0.074200 0.794062 0.031 Uiso 1 1 calc R U . . .
H13C H 0.563436 -0.019627 0.830203 0.031 Uiso 1 1 calc R U . . .
Cl02 Cl 0.45565(13) 0.93062(10) 0.39041(4) 0.0162(2) Uani 1 1 d . . . . .


_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 1.839(3) . ?
Se1 C1 1.866(4) . ?
O1 C10 1.384(4) . ?
O1 C13 1.430(5) . ?
N2 C1 1.365(4) . ?
N2 C5 1.370(5) . ?
N2 C6 1.441(5) . ?
N1 C6 1.285(5) . ?
N3 H3 0.8800 . ?
N3 C6 1.361(5) . ?
N3 C7 1.418(5) . ?
C1 C2 1.394(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.371(5) . ?
C3 H3A 0.9500 . ?
C3 C4 1.413(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.362(5) . ?
C5 H5 0.9500 . ?
C7 C8 1.394(5) . ?
C7 C12 1.399(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.396(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.398(5) . ?
C10 C11 1.393(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.376(5) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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 C1 88.48(15) . . ?
C10 O1 C13 117.2(3) . . ?
C1 N2 C5 120.6(3) . . ?
C1 N2 C6 113.8(3) . . ?
C5 N2 C6 125.5(3) . . ?
C6 N1 Se1 111.2(3) . . ?
C6 N3 H3 117.9 . . ?
C6 N3 C7 124.1(3) . . ?
C7 N3 H3 117.9 . . ?
N2 C1 Se1 109.0(3) . . ?
N2 C1 C2 120.4(3) . . ?
C2 C1 Se1 130.6(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.3(4) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C2 C3 C4 119.5(4) . . ?
C4 C3 H3A 120.3 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4 120.0 . . ?
N2 C5 H5 119.9 . . ?
C4 C5 N2 120.1(4) . . ?
C4 C5 H5 119.9 . . ?
N1 C6 N2 117.3(3) . . ?
N1 C6 N3 126.2(3) . . ?
N3 C6 N2 116.5(3) . . ?
C8 C7 N3 124.0(3) . . ?
C8 C7 C12 118.9(4) . . ?
C12 C7 N3 117.0(4) . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.5(3) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.7(4) . . ?
C10 C9 H9 120.2 . . ?
O1 C10 C9 124.1(4) . . ?
O1 C10 C11 116.0(3) . . ?
C11 C10 C9 119.9(4) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 121.1(4) . . ?
C11 C12 H12 119.5 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
Se1 N1 C6 N2 1.1(4) . . . . ?
Se1 N1 C6 N3 -179.6(3) . . . . ?
Se1 C1 C2 C3 175.5(3) . . . . ?
O1 C10 C11 C12 177.3(3) . . . . ?
N2 C1 C2 C3 -1.9(5) . . . . ?
N1 Se1 C1 N2 -2.3(3) . . . . ?
N1 Se1 C1 C2 -180.0(4) . . . . ?
N3 C7 C8 C9 -178.7(3) . . . . ?
N3 C7 C12 C11 177.7(4) . . . . ?
C1 Se1 N1 C6 0.7(3) . . . . ?
C1 N2 C5 C4 -2.7(6) . . . . ?
C1 N2 C6 N1 -3.1(5) . . . . ?
C1 N2 C6 N3 177.5(3) . . . . ?
C1 C2 C3 C4 -0.7(6) . . . . ?
C2 C3 C4 C5 1.7(6) . . . . ?
C3 C4 C5 N2 0.0(6) . . . . ?
C5 N2 C1 Se1 -174.2(3) . . . . ?
C5 N2 C1 C2 3.7(5) . . . . ?
C5 N2 C6 N1 174.4(4) . . . . ?
C5 N2 C6 N3 -5.0(5) . . . . ?
C6 N2 C1 Se1 3.4(4) . . . . ?
C6 N2 C1 C2 -178.7(3) . . . . ?
C6 N2 C5 C4 179.9(3) . . . . ?
C6 N3 C7 C8 -28.2(6) . . . . ?
C6 N3 C7 C12 155.4(4) . . . . ?
C7 N3 C6 N2 173.0(3) . . . . ?
C7 N3 C6 N1 -6.3(6) . . . . ?
C7 C8 C9 C10 2.0(6) . . . . ?
C8 C7 C12 C11 1.1(6) . . . . ?
C8 C9 C10 O1 -178.4(3) . . . . ?
C8 C9 C10 C11 -0.2(6) . . . . ?
C9 C10 C11 C12 -1.1(6) . . . . ?
C10 C11 C12 C7 0.7(6) . . . . ?
C12 C7 C8 C9 -2.4(6) . . . . ?
C13 O1 C10 C9 8.4(5) . . . . ?
C13 O1 C10 C11 -169.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_21kub201_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2254286'
loop_
_audit_author_name
_audit_author_address
'Alexey Kubasov'
;Kurnakov Institute of General and Inorganic Chemistry
Russia
;
_audit_update_record             
;
2023-04-05 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;
_audit_creation_date             2023-04-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H12 N3 O Se, Cl, H2 O'
_chemical_formula_sum            'C10 H14 Cl N3 O2 Se'
_chemical_formula_weight         322.65
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   5.3306(7)
_cell_length_b                   14.043(4)
_cell_length_c                   16.798(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.025(4)
_cell_angle_gamma                90
_cell_volume                     1255.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3634
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.108
_cell_measurement_theta_min      2.836
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.250
_exptl_absorpt_coefficient_mu    3.197
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.4566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1243 before and 0.0345 after correction.
The Ratio of minimum to maximum transmission is 0.5773.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6030
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         1.891
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2262
_reflns_number_total             2763
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2763
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0286
_refine_ls_restrained_S_all      1.025
_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)+(0.0223P)²+0.8152P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0576
_refine_ls_wR_factor_ref         0.0609
_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 O(H,H) groups
2.a Free rotating group:
 O2(H2A,H2B)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Se1 Se 0.42519(4) 0.49684(2) 0.38295(2) 0.01067(7) Uani 1 1 d . . . . .
O1 O 1.2146(3) 0.83290(12) 0.52439(10) 0.0159(4) Uani 1 1 d . . . . .
N1 N 0.6512(4) 0.56809(15) 0.44626(12) 0.0121(4) Uani 1 1 d . . . . .
N2 N 0.7631(4) 0.61029(14) 0.31901(12) 0.0092(4) Uani 1 1 d . . . . .
N3 N 0.9732(4) 0.68393(14) 0.43321(12) 0.0111(4) Uani 1 1 d . . . . .
C1 C 0.5673(4) 0.55266(17) 0.29415(15) 0.0108(5) Uani 1 1 d . . . . .
C2 C 0.5099(5) 0.54058(18) 0.21248(15) 0.0133(5) Uani 1 1 d . . . . .
H2 H 0.369933 0.503259 0.194080 0.016 Uiso 1 1 calc R U . . .
C3 C 0.6613(5) 0.58411(18) 0.15959(15) 0.0139(5) Uani 1 1 d . . . . .
H3 H 0.621352 0.578917 0.103974 0.017 Uiso 1 1 calc R U . . .
C4 C 0.8741(5) 0.63616(17) 0.18660(15) 0.0138(5) Uani 1 1 d . . . . .
H4 H 0.983500 0.662249 0.149449 0.017 Uiso 1 1 calc R U . . .
C5 C 0.9230(5) 0.64912(17) 0.26650(15) 0.0125(5) Uani 1 1 d . . . . .
H5 H 1.065845 0.684536 0.285440 0.015 Uiso 1 1 calc R U . . .
C6 C 0.7919(4) 0.61960(17) 0.40436(14) 0.0098(5) Uani 1 1 d . . . . .
C7 C 1.0452(4) 0.67043(18) 0.51892(14) 0.0120(5) Uani 1 1 d . . . . .
H7A H 1.089859 0.603001 0.529418 0.014 Uiso 1 1 calc R U . . .
H7B H 0.902835 0.687412 0.551703 0.014 Uiso 1 1 calc R U . . .
C8 C 1.2688(5) 0.73404(18) 0.54025(16) 0.0150(5) Uani 1 1 d . . . . .
H8A H 1.318217 0.726115 0.597505 0.018 Uiso 1 1 calc R U . . .
H8B H 1.412459 0.714077 0.509152 0.018 Uiso 1 1 calc R U . . .
C9 C 1.1413(5) 0.84559(18) 0.44159(15) 0.0167(6) Uani 1 1 d . . . . .
H9A H 1.281942 0.826979 0.408668 0.020 Uiso 1 1 calc R U . . .
H9B H 1.103452 0.913621 0.431209 0.020 Uiso 1 1 calc R U . . .
C10 C 0.9114(5) 0.78585(17) 0.41802(15) 0.0135(5) Uani 1 1 d . . . . .
H10A H 0.768354 0.805187 0.449657 0.016 Uiso 1 1 calc R U . . .
H10B H 0.863085 0.795486 0.360867 0.016 Uiso 1 1 calc R U . . .
Cl1 Cl 0.06122(11) 0.39790(4) 0.27747(4) 0.01299(13) Uani 1 1 d . . . . .
O2 O 0.4332(3) 0.78051(13) 0.26171(12) 0.0209(4) Uani 1 1 d G . . . .
H2A H 0.570322 0.805627 0.245189 0.031 Uiso 1 1 d G U . . .
H2B H 0.306964 0.818019 0.249672 0.031 Uiso 1 1 d G 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 1.857(2) . ?
Se1 C1 1.879(2) . ?
O1 C8 1.440(3) . ?
O1 C9 1.436(3) . ?
N1 C6 1.279(3) . ?
N2 C1 1.369(3) . ?
N2 C5 1.372(3) . ?
N2 C6 1.440(3) . ?
N3 C6 1.392(3) . ?
N3 C7 1.483(3) . ?
N3 C10 1.488(3) . ?
C1 C2 1.400(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.375(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.404(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.366(3) . ?
C5 H5 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.517(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.520(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
O2 H2A 0.8700 . ?
O2 H2B 0.8701 . ?

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 C1 87.33(10) . . ?
C9 O1 C8 109.91(19) . . ?
C6 N1 Se1 111.77(16) . . ?
C1 N2 C5 121.9(2) . . ?
C1 N2 C6 113.38(19) . . ?
C5 N2 C6 124.55(19) . . ?
C6 N3 C7 113.25(19) . . ?
C6 N3 C10 114.91(19) . . ?
C7 N3 C10 109.46(19) . . ?
N2 C1 Se1 109.72(17) . . ?
N2 C1 C2 119.6(2) . . ?
C2 C1 Se1 130.61(19) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.3(2) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.9(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.1 . . ?
N2 C5 H5 120.5 . . ?
C4 C5 N2 119.1(2) . . ?
C4 C5 H5 120.5 . . ?
N1 C6 N2 117.5(2) . . ?
N1 C6 N3 126.3(2) . . ?
N3 C6 N2 116.2(2) . . ?
N3 C7 H7A 110.0 . . ?
N3 C7 H7B 110.0 . . ?
N3 C7 C8 108.3(2) . . ?
H7A C7 H7B 108.4 . . ?
C8 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
O1 C8 C7 112.1(2) . . ?
O1 C8 H8A 109.2 . . ?
O1 C8 H8B 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
O1 C9 H9A 109.4 . . ?
O1 C9 H9B 109.4 . . ?
O1 C9 C10 111.0(2) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
N3 C10 C9 108.5(2) . . ?
N3 C10 H10A 110.0 . . ?
N3 C10 H10B 110.0 . . ?
C9 C10 H10A 110.0 . . ?
C9 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
H2A O2 H2B 109.4 . . ?

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
Se1 N1 C6 N2 -3.3(3) . . . . ?
Se1 N1 C6 N3 177.21(19) . . . . ?
Se1 C1 C2 C3 -173.92(19) . . . . ?
O1 C9 C10 N3 -59.7(3) . . . . ?
N1 Se1 C1 N2 3.12(17) . . . . ?
N1 Se1 C1 C2 -179.8(2) . . . . ?
N2 C1 C2 C3 2.9(3) . . . . ?
N3 C7 C8 O1 58.5(3) . . . . ?
C1 Se1 N1 C6 0.09(18) . . . . ?
C1 N2 C5 C4 5.3(3) . . . . ?
C1 N2 C6 N1 6.0(3) . . . . ?
C1 N2 C6 N3 -174.4(2) . . . . ?
C1 C2 C3 C4 2.6(4) . . . . ?
C2 C3 C4 C5 -4.3(4) . . . . ?
C3 C4 C5 N2 0.4(4) . . . . ?
C5 N2 C1 Se1 170.47(17) . . . . ?
C5 N2 C1 C2 -7.0(3) . . . . ?
C5 N2 C6 N1 -169.8(2) . . . . ?
C5 N2 C6 N3 9.8(3) . . . . ?
C6 N2 C1 Se1 -5.5(2) . . . . ?
C6 N2 C1 C2 177.1(2) . . . . ?
C6 N2 C5 C4 -179.3(2) . . . . ?
C6 N3 C7 C8 171.7(2) . . . . ?
C6 N3 C10 C9 -171.6(2) . . . . ?
C7 N3 C6 N1 16.2(3) . . . . ?
C7 N3 C6 N2 -163.32(19) . . . . ?
C7 N3 C10 C9 59.6(3) . . . . ?
C8 O1 C9 C10 58.8(3) . . . . ?
C9 O1 C8 C7 -58.6(3) . . . . ?
C10 N3 C6 N1 -110.7(3) . . . . ?
C10 N3 C6 N2 69.9(3) . . . . ?
C10 N3 C7 C8 -58.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 2254288'
loop_
_audit_author_name
_audit_author_address
'Alexey Kubasov'
;Kurnakov Institute of General and Inorganic Chemistry
Russia
;
_audit_update_record             
;
2023-04-05 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;
_audit_creation_date             2023-04-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H11 N4 Se, Cl'
_chemical_formula_sum            'C9 H11 Cl N4 Se'
_chemical_formula_weight         289.63
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_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      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   11.922(4)
_cell_length_b                   6.546(3)
_cell_length_c                   14.620(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.226(16)
_cell_angle_gamma                90
_cell_volume                     1083.7(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3470
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.973
_cell_measurement_theta_min      2.939
_shelx_estimated_absorpt_T_max   0.710
_shelx_estimated_absorpt_T_min   0.216
_exptl_absorpt_coefficient_mu    3.682
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.4174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1273 before and 0.0486 after correction.
The Ratio of minimum to maximum transmission is 0.5595.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.775
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6556
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.023
_diffrn_reflns_theta_min         2.934
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2532
_reflns_number_total             3107
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.739
_refine_diff_density_min         -1.074
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         3107
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.027
_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)+(0.0315P)²+1.3213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0888
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Se1 Se 0.64316(2) 0.77428(4) 0.71804(2) 0.01309(9) Uani 1 1 d . . . . .
N1 N 0.4903(2) 0.7366(4) 0.63592(17) 0.0151(5) Uani 1 1 d . . . . .
N2 N 0.5957(2) 0.7699(3) 0.52767(16) 0.0116(4) Uani 1 1 d . . . . .
N3 N 0.3900(2) 0.7205(3) 0.46493(16) 0.0127(4) Uani 1 1 d . . . . .
N4 N 0.1884(2) 0.6794(3) 0.40507(16) 0.0125(4) Uani 1 1 d . . . . .
C1 C 0.6908(2) 0.7917(4) 0.60804(19) 0.0115(5) Uani 1 1 d . . . . .
C2 C 0.8034(2) 0.8202(4) 0.5985(2) 0.0135(5) Uani 1 1 d . . . . .
H2 H 0.871251 0.832512 0.653623 0.016 Uiso 1 1 calc R U . . .
C3 C 0.8129(3) 0.8300(4) 0.5066(2) 0.0148(5) Uani 1 1 d . . . . .
H3 H 0.888109 0.851398 0.498586 0.018 Uiso 1 1 calc R U . . .
C4 C 0.7136(3) 0.8087(4) 0.4256(2) 0.0166(5) Uani 1 1 d . . . . .
H4 H 0.721424 0.816078 0.363030 0.020 Uiso 1 1 calc R U . . .
C5 C 0.6049(3) 0.7772(4) 0.43629(19) 0.0145(5) Uani 1 1 d . . . . .
H5 H 0.536988 0.760772 0.381531 0.017 Uiso 1 1 calc R U . . .
C6 C 0.4845(2) 0.7401(4) 0.5464(2) 0.0128(5) Uani 1 1 d . . . . .
C7 C 0.2858(2) 0.6995(4) 0.47797(19) 0.0134(5) Uani 1 1 d . . . . .
H7 H 0.281130 0.698803 0.541667 0.016 Uiso 1 1 calc R U . . .
C8 C 0.1869(3) 0.6861(4) 0.3043(2) 0.0181(6) Uani 1 1 d . . . . .
H8A H 0.148913 0.562322 0.270913 0.027 Uiso 1 1 calc R U . . .
H8B H 0.268038 0.693842 0.301949 0.027 Uiso 1 1 calc R U . . .
H8C H 0.142650 0.806452 0.272634 0.027 Uiso 1 1 calc R U . . .
C9 C 0.0728(2) 0.6629(5) 0.4200(2) 0.0179(5) Uani 1 1 d . . . . .
H9A H 0.023866 0.780313 0.390311 0.027 Uiso 1 1 calc R U . . .
H9B H 0.083184 0.661015 0.489212 0.027 Uiso 1 1 calc R U . . .
H9C H 0.033924 0.536507 0.390519 0.027 Uiso 1 1 calc R U . . .
Cl1 Cl 0.88564(6) 0.83298(10) 0.83825(5) 0.01664(14) Uani 1 1 d . . . . .


_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 1.859(2) . ?
Se1 C1 1.869(3) . ?
N1 C6 1.290(4) . ?
N2 C1 1.361(3) . ?
N2 C5 1.375(3) . ?
N2 C6 1.448(3) . ?
N3 C6 1.366(3) . ?
N3 C7 1.322(3) . ?
N4 C7 1.314(3) . ?
N4 C8 1.469(3) . ?
N4 C9 1.466(3) . ?
C1 C2 1.405(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.368(4) . ?
C5 H5 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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 C1 87.29(11) . . ?
C6 N1 Se1 112.58(19) . . ?
C1 N2 C5 122.5(2) . . ?
C1 N2 C6 114.6(2) . . ?
C5 N2 C6 123.0(2) . . ?
C7 N3 C6 116.1(2) . . ?
C7 N4 C8 122.8(2) . . ?
C7 N4 C9 121.3(2) . . ?
C9 N4 C8 115.8(2) . . ?
N2 C1 Se1 109.94(18) . . ?
N2 C1 C2 119.5(2) . . ?
C2 C1 Se1 130.6(2) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.9(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 120.0 . . ?
N2 C5 H5 120.6 . . ?
C4 C5 N2 118.8(3) . . ?
C4 C5 H5 120.6 . . ?
N1 C6 N2 115.6(2) . . ?
N1 C6 N3 130.6(3) . . ?
N3 C6 N2 113.8(2) . . ?
N3 C7 H7 119.2 . . ?
N4 C7 N3 121.7(2) . . ?
N4 C7 H7 119.2 . . ?
N4 C8 H8A 109.5 . . ?
N4 C8 H8B 109.5 . . ?
N4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
Se1 N1 C6 N2 0.6(3) . . . . ?
Se1 N1 C6 N3 -179.3(2) . . . . ?
Se1 C1 C2 C3 -179.2(2) . . . . ?
N1 Se1 C1 N2 0.12(18) . . . . ?
N1 Se1 C1 C2 -179.2(2) . . . . ?
N2 C1 C2 C3 1.5(4) . . . . ?
C1 Se1 N1 C6 -0.4(2) . . . . ?
C1 N2 C5 C4 -0.3(4) . . . . ?
C1 N2 C6 N1 -0.5(3) . . . . ?
C1 N2 C6 N3 179.4(2) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 N2 0.9(4) . . . . ?
C5 N2 C1 Se1 179.69(19) . . . . ?
C5 N2 C1 C2 -0.9(4) . . . . ?
C5 N2 C6 N1 180.0(2) . . . . ?
C5 N2 C6 N3 -0.1(3) . . . . ?
C6 N2 C1 Se1 0.2(3) . . . . ?
C6 N2 C1 C2 179.6(2) . . . . ?
C6 N2 C5 C4 179.1(2) . . . . ?
C6 N3 C7 N4 180.0(2) . . . . ?
C7 N3 C6 N1 1.9(4) . . . . ?
C7 N3 C6 N2 -177.9(2) . . . . ?
C8 N4 C7 N3 -2.3(4) . . . . ?
C9 N4 C7 N3 -177.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_21kub147_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2254289'
loop_
_audit_author_name
_audit_author_address
'Alexey Kubasov'
;Kurnakov Institute of General and Inorganic Chemistry
Russia
;
_audit_update_record             
;
2023-04-05 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_mo_21kub147_0m_a    
;
PROBLEM: Short Inter D...A Contact  Se1      ..O1       .       2.79 Ang.
RESPONSE: O-chalcogen bonding
;
# Added during the CSD deposition process: Wednesday 05 April 2023 04:28 PM
# end Validation Reply Form

_audit_creation_date             2023-04-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H10 N3 Se, Cl O4'
_chemical_formula_sum            'C8 H10 Cl N3 O4 Se'
_chemical_formula_weight         326.60
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8384(15)
_cell_length_b                   9.403(2)
_cell_length_c                   10.236(2)
_cell_angle_alpha                67.561(9)
_cell_angle_beta                 74.848(10)
_cell_angle_gamma                70.534(11)
_cell_volume                     566.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6093
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      33.846
_cell_measurement_theta_min      2.693
_shelx_estimated_absorpt_T_max   0.537
_shelx_estimated_absorpt_T_min   0.269
_exptl_absorpt_coefficient_mu    3.555
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.5047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0857 before and 0.0293 after correction.
The Ratio of minimum to maximum transmission is 0.6759.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.914
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5966
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         2.428
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3074
_reflns_number_total             3260
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0212
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0172P)²+0.2999P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0497
_refine_ls_wR_factor_ref         0.0504
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Se1 Se 0.35595(2) 0.88416(2) 0.45270(2) 0.01092(5) Uani 1 1 d . . . . .
N1 N 0.3460(2) 0.91513(15) 0.62084(13) 0.0127(2) Uani 1 1 d . . . . .
N2 N 0.08631(19) 0.78276(15) 0.68274(13) 0.0103(2) Uani 1 1 d . . . . .
N3 N 0.1663(2) 0.85787(15) 0.85907(13) 0.0127(2) Uani 1 1 d . . . . .
C1 C 0.1423(2) 0.78145(17) 0.54481(15) 0.0114(3) Uani 1 1 d . . . . .
C2 C 0.0334(2) 0.71783(18) 0.49187(16) 0.0132(3) Uani 1 1 d . . . . .
H2 H 0.072819 0.714752 0.396651 0.016 Uiso 1 1 calc R U . . .
C3 C -0.1320(2) 0.65979(18) 0.58054(17) 0.0145(3) Uani 1 1 d . . . . .
H3 H -0.206514 0.614832 0.546994 0.017 Uiso 1 1 calc R U . . .
C4 C -0.1908(2) 0.66702(18) 0.72113(16) 0.0142(3) Uani 1 1 d . . . . .
H4 H -0.305993 0.628032 0.781634 0.017 Uiso 1 1 calc R U . . .
C5 C -0.0830(2) 0.72975(18) 0.77042(16) 0.0132(3) Uani 1 1 d . . . . .
H5 H -0.124237 0.736798 0.864338 0.016 Uiso 1 1 calc R U . . .
C6 C 0.2104(2) 0.85324(17) 0.72128(15) 0.0114(3) Uani 1 1 d . . . . .
C7 C 0.2550(3) 0.9701(2) 0.87807(17) 0.0177(3) Uani 1 1 d . . . . .
H7A H 0.408345 0.930658 0.867214 0.027 Uiso 1 1 calc R U . . .
H7B H 0.200269 0.979471 0.973798 0.027 Uiso 1 1 calc R U . . .
H7C H 0.215584 1.074797 0.805878 0.027 Uiso 1 1 calc R U . . .
C8 C 0.1999(3) 0.70211(19) 0.97581(16) 0.0163(3) Uani 1 1 d . . . . .
H8A H 0.170671 0.623080 0.948258 0.024 Uiso 1 1 calc R U . . .
H8B H 0.105458 0.713989 1.063473 0.024 Uiso 1 1 calc R U . . .
H8C H 0.345808 0.666558 0.992672 0.024 Uiso 1 1 calc R U . . .
Cl1 Cl 0.58541(5) 0.64140(4) 0.21956(3) 0.01140(7) Uani 1 1 d . . . . .
O1 O 0.39990(18) 0.77183(14) 0.22757(12) 0.0182(2) Uani 1 1 d . . . . .
O2 O 0.73262(19) 0.63437(15) 0.30148(13) 0.0205(2) Uani 1 1 d . . . . .
O3 O 0.5248(2) 0.49383(15) 0.27510(15) 0.0244(3) Uani 1 1 d . . . . .
O4 O 0.6811(2) 0.66646(17) 0.07192(12) 0.0239(3) Uani 1 1 d . . . . .


_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 1.8328(13) . ?
Se1 C1 1.8661(16) . ?
N1 C6 1.2881(19) . ?
N2 C1 1.3666(18) . ?
N2 C5 1.3763(19) . ?
N2 C6 1.4370(19) . ?
N3 C6 1.3776(18) . ?
N3 C7 1.471(2) . ?
N3 C8 1.486(2) . ?
C1 C2 1.400(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.377(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.411(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.363(2) . ?
C5 H5 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
Cl1 O1 1.4511(12) . ?
Cl1 O2 1.4407(12) . ?
Cl1 O3 1.4416(13) . ?
Cl1 O4 1.4428(12) . ?

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 C1 88.03(6) . . ?
C6 N1 Se1 111.97(10) . . ?
C1 N2 C5 121.46(12) . . ?
C1 N2 C6 113.79(12) . . ?
C5 N2 C6 124.63(12) . . ?
C6 N3 C7 113.86(12) . . ?
C6 N3 C8 116.85(12) . . ?
C7 N3 C8 111.89(12) . . ?
N2 C1 Se1 109.37(10) . . ?
N2 C1 C2 120.10(14) . . ?
C2 C1 Se1 130.41(11) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.71(14) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.10(14) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.23(14) . . ?
C5 C4 H4 119.9 . . ?
N2 C5 H5 120.3 . . ?
C4 C5 N2 119.31(14) . . ?
C4 C5 H5 120.3 . . ?
N1 C6 N2 116.68(13) . . ?
N1 C6 N3 125.50(14) . . ?
N3 C6 N2 117.70(13) . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 Cl1 O1 110.03(7) . . ?
O2 Cl1 O3 109.84(8) . . ?
O2 Cl1 O4 109.67(8) . . ?
O3 Cl1 O1 109.17(8) . . ?
O3 Cl1 O4 109.09(8) . . ?
O4 Cl1 O1 109.02(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
Se1 N1 C6 N2 -3.79(17) . . . . ?
Se1 N1 C6 N3 -179.56(12) . . . . ?
Se1 C1 C2 C3 -174.38(12) . . . . ?
N1 Se1 C1 N2 0.86(10) . . . . ?
N1 Se1 C1 C2 176.72(15) . . . . ?
N2 C1 C2 C3 1.1(2) . . . . ?
C1 Se1 N1 C6 1.65(11) . . . . ?
C1 N2 C5 C4 3.4(2) . . . . ?
C1 N2 C6 N1 4.63(19) . . . . ?
C1 N2 C6 N3 -179.26(12) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C3 C4 C5 N2 -1.4(2) . . . . ?
C5 N2 C1 Se1 173.07(11) . . . . ?
C5 N2 C1 C2 -3.3(2) . . . . ?
C5 N2 C6 N1 -171.29(14) . . . . ?
C5 N2 C6 N3 4.8(2) . . . . ?
C6 N2 C1 Se1 -2.99(15) . . . . ?
C6 N2 C1 C2 -179.35(13) . . . . ?
C6 N2 C5 C4 179.01(14) . . . . ?
C7 N3 C6 N1 12.4(2) . . . . ?
C7 N3 C6 N2 -163.32(13) . . . . ?
C8 N3 C6 N1 -120.50(17) . . . . ?
C8 N3 C6 N2 63.77(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_21kub178_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2254285'
loop_
_audit_author_name
_audit_author_address
'Alexey Kubasov'
;Kurnakov Institute of General and Inorganic Chemistry
Russia
;
_audit_update_record             
;
2023-04-05 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;
_audit_creation_date             2023-04-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 N3 Se, Cl'
_chemical_formula_sum            'C16 H12 Cl N3 Se'
_chemical_formula_weight         360.70
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_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           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   7.811(4)
_cell_length_b                   7.811
_cell_length_c                   23.699(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1445.9(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8786
_cell_measurement_temperature    300.0
_cell_measurement_theta_max      30.580
_cell_measurement_theta_min      2.611
_shelx_estimated_absorpt_T_max   0.403
_shelx_estimated_absorpt_T_min   0.287
_exptl_absorpt_coefficient_mu    2.777
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.5204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0907 before and 0.0709 after correction.
The Ratio of minimum to maximum transmission is 0.6973.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12885
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.465
_diffrn_reflns_theta_min         2.608
_diffrn_ambient_temperature      300(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                3136
_reflns_number_total             3287
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.682
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 
;
 Flack x determined using 1420 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.040(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3287
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0363P)²+0.8187P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0866
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C3(H3A), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C12(H12),
 C13(H13), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Se1 Se 0.91807(6) 0.72805(7) 0.40735(2) 0.04203(15) Uani 1 1 d . . . . .
N1 N 0.8164(7) 0.7111(7) 0.4773(2) 0.0533(12) Uani 1 1 d . . . . .
N2 N 0.5979(5) 0.8276(5) 0.42334(17) 0.0366(9) Uani 1 1 d . . . . .
N3 N 0.5495(8) 0.7608(9) 0.5203(2) 0.0732(19) Uani 1 1 d . . . . .
H3 H 0.457447 0.820984 0.518850 0.088 Uiso 1 1 calc R U . . .
C1 C 0.7149(6) 0.8249(6) 0.3810(2) 0.0357(10) Uani 1 1 d . . . . .
C2 C 0.6721(7) 0.8875(7) 0.3281(2) 0.0433(11) Uani 1 1 d . . . . .
H2 H 0.753541 0.892927 0.299509 0.052 Uiso 1 1 calc R U . . .
C3 C 0.5079(8) 0.9413(7) 0.3188(2) 0.0471(12) Uani 1 1 d . . . . .
H3A H 0.476919 0.982788 0.283444 0.056 Uiso 1 1 calc R U . . .
C4 C 0.3856(7) 0.9342(7) 0.3622(2) 0.0435(12) Uani 1 1 d . . . . .
H4 H 0.273208 0.967579 0.355295 0.052 Uiso 1 1 calc R U . . .
C5 C 0.4322(6) 0.8784(7) 0.4141(2) 0.0428(11) Uani 1 1 d . . . . .
H5 H 0.352433 0.874586 0.443193 0.051 Uiso 1 1 calc R U . . .
C6 C 0.6615(8) 0.7627(8) 0.4762(2) 0.0486(13) Uani 1 1 d . . . . .
C7 C 0.5860(8) 0.6560(9) 0.5704(3) 0.0545(14) Uani 1 1 d . . . . .
C8 C 0.5359(8) 0.4940(8) 0.5742(3) 0.0543(14) Uani 1 1 d . . . . .
H8 H 0.477435 0.448116 0.543496 0.065 Uiso 1 1 calc R U . . .
C9 C 0.5640(9) 0.3858(8) 0.6209(3) 0.0550(14) Uani 1 1 d . . . . .
H9 H 0.527532 0.272480 0.621007 0.066 Uiso 1 1 calc R U . . .
C10 C 0.6500(8) 0.4576(8) 0.6674(3) 0.0581(15) Uani 1 1 d . . . . .
H10 H 0.674462 0.391772 0.699126 0.070 Uiso 1 1 calc R U . . .
C11 C 0.7000(6) 0.6381(7) 0.6649(2) 0.0404(10) Uani 1 1 d . . . . .
C12 C 0.7803(8) 0.7114(10) 0.7123(3) 0.0573(16) Uani 1 1 d . . . . .
H12 H 0.801309 0.644700 0.744092 0.069 Uiso 1 1 calc R U . . .
C13 C 0.8267(10) 0.8770(11) 0.7119(4) 0.0682(19) Uani 1 1 d . . . . .
H13 H 0.878520 0.926051 0.743343 0.082 Uiso 1 1 calc R U . . .
C14 C 0.7950(7) 0.9763(8) 0.6626(3) 0.0556(14) Uani 1 1 d . . . . .
H14 H 0.827219 1.090896 0.662887 0.067 Uiso 1 1 calc R U . . .
C15 C 0.7223(8) 0.9149(8) 0.6160(3) 0.0570(15) Uani 1 1 d . . . . .
H15 H 0.705068 0.984228 0.584630 0.068 Uiso 1 1 calc R U . . .
C16 C 0.6684(7) 0.7290(8) 0.6156(2) 0.0488(13) Uani 1 1 d . . . . .
Cl1 Cl 1.05696(18) 0.7257(2) 0.28829(6) 0.0518(3) Uani 1 1 d . . . . .


_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 1.843(5) . ?
Se1 C1 1.865(5) . ?
N1 C6 1.276(8) . ?
N2 C1 1.358(7) . ?
N2 C5 1.372(6) . ?
N2 C6 1.440(7) . ?
N3 H3 0.8600 . ?
N3 C6 1.363(8) . ?
N3 C7 1.469(8) . ?
C1 C2 1.387(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(8) . ?
C3 H3A 0.9300 . ?
C3 C4 1.405(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.355(8) . ?
C5 H5 0.9300 . ?
C7 C8 1.327(10) . ?
C7 C16 1.375(9) . ?
C8 H8 0.9300 . ?
C8 C9 1.411(9) . ?
C9 H9 0.9300 . ?
C9 C10 1.407(10) . ?
C10 H10 0.9300 . ?
C10 C11 1.464(8) . ?
C11 C12 1.409(9) . ?
C11 C16 1.388(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.344(11) . ?
C13 H13 0.9300 . ?
C13 C14 1.425(11) . ?
C14 H14 0.9300 . ?
C14 C15 1.330(10) . ?
C15 H15 0.9300 . ?
C15 C16 1.512(9) . ?

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 C1 87.9(2) . . ?
C6 N1 Se1 111.5(4) . . ?
C1 N2 C5 121.4(4) . . ?
C1 N2 C6 113.9(4) . . ?
C5 N2 C6 124.5(5) . . ?
C6 N3 H3 120.0 . . ?
C6 N3 C7 120.1(5) . . ?
C7 N3 H3 120.0 . . ?
N2 C1 Se1 109.4(3) . . ?
N2 C1 C2 120.0(5) . . ?
C2 C1 Se1 130.6(4) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.7(5) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3A 119.7 . . ?
C2 C3 C4 120.5(5) . . ?
C4 C3 H3A 119.7 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.6(5) . . ?
C5 C4 H4 120.2 . . ?
N2 C5 H5 120.3 . . ?
C4 C5 N2 119.5(5) . . ?
C4 C5 H5 120.3 . . ?
N1 C6 N2 117.1(5) . . ?
N1 C6 N3 126.1(5) . . ?
N3 C6 N2 116.7(5) . . ?
C8 C7 N3 121.9(7) . . ?
C8 C7 C16 118.7(6) . . ?
C16 C7 N3 119.3(7) . . ?
C7 C8 H8 117.3 . . ?
C7 C8 C9 125.3(6) . . ?
C9 C8 H8 117.3 . . ?
C8 C9 H9 121.6 . . ?
C10 C9 C8 116.8(6) . . ?
C10 C9 H9 121.6 . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.6(6) . . ?
C11 C10 H10 120.7 . . ?
C12 C11 C10 118.5(6) . . ?
C16 C11 C10 118.6(5) . . ?
C16 C11 C12 122.8(6) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(7) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.9(7) . . ?
C14 C13 H13 120.6 . . ?
C13 C14 H14 118.0 . . ?
C15 C14 C13 124.0(6) . . ?
C15 C14 H14 118.0 . . ?
C14 C15 H15 121.0 . . ?
C14 C15 C16 118.0(6) . . ?
C16 C15 H15 121.0 . . ?
C7 C16 C11 121.8(6) . . ?
C7 C16 C15 122.2(6) . . ?
C11 C16 C15 115.9(6) . . ?

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
Se1 N1 C6 N2 -1.9(8) . . . . ?
Se1 N1 C6 N3 177.4(6) . . . . ?
Se1 C1 C2 C3 175.3(4) . . . . ?
N1 Se1 C1 N2 -2.5(4) . . . . ?
N1 Se1 C1 C2 178.1(5) . . . . ?
N2 C1 C2 C3 -4.1(8) . . . . ?
N3 C7 C8 C9 -179.2(6) . . . . ?
N3 C7 C16 C11 177.4(5) . . . . ?
N3 C7 C16 C15 0.4(8) . . . . ?
C1 Se1 N1 C6 2.5(5) . . . . ?
C1 N2 C5 C4 -2.9(8) . . . . ?
C1 N2 C6 N1 -0.1(8) . . . . ?
C1 N2 C6 N3 -179.5(6) . . . . ?
C1 C2 C3 C4 0.5(8) . . . . ?
C2 C3 C4 C5 2.0(9) . . . . ?
C3 C4 C5 N2 -0.8(8) . . . . ?
C5 N2 C1 Se1 -174.1(4) . . . . ?
C5 N2 C1 C2 5.4(7) . . . . ?
C5 N2 C6 N1 175.9(5) . . . . ?
C5 N2 C6 N3 -3.4(9) . . . . ?
C6 N2 C1 Se1 2.1(5) . . . . ?
C6 N2 C1 C2 -178.4(5) . . . . ?
C6 N2 C5 C4 -178.6(5) . . . . ?
C6 N3 C7 C8 -89.0(9) . . . . ?
C6 N3 C7 C16 93.7(8) . . . . ?
C7 N3 C6 N1 -16.1(12) . . . . ?
C7 N3 C6 N2 163.2(6) . . . . ?
C7 C8 C9 C10 1.1(10) . . . . ?
C8 C7 C16 C11 -0.1(8) . . . . ?
C8 C7 C16 C15 -177.0(6) . . . . ?
C8 C9 C10 C11 1.5(9) . . . . ?
C9 C10 C11 C12 177.7(5) . . . . ?
C9 C10 C11 C16 -3.2(8) . . . . ?
C10 C11 C12 C13 -179.3(6) . . . . ?
C10 C11 C16 C7 2.5(8) . . . . ?
C10 C11 C16 C15 179.7(5) . . . . ?
C11 C12 C13 C14 -0.7(10) . . . . ?
C12 C11 C16 C7 -178.4(5) . . . . ?
C12 C11 C16 C15 -1.2(8) . . . . ?
C12 C13 C14 C15 -0.3(11) . . . . ?
C13 C14 C15 C16 0.6(10) . . . . ?
C14 C15 C16 C7 177.3(6) . . . . ?
C14 C15 C16 C11 0.2(8) . . . . ?
C16 C7 C8 C9 -1.8(10) . . . . ?
C16 C11 C12 C13 1.6(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_or-154_a
_database_code_depnum_ccdc_archive 'CCDC 2254290'
loop_
_audit_author_name
_audit_author_address
'Alexey Kubasov'
;Kurnakov Institute of General and Inorganic Chemistry
Russia
;
_audit_update_record             
;
2023-04-05 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;
_audit_creation_date             2023-04-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H10 N3 Se, C24 H20 B'
_chemical_formula_sum            'C32 H30 B N3 Se'
_chemical_formula_weight         546.36
_chemical_melting_point          ?
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'
B B 0.0013 0.0007 '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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   15.3881(6)
_cell_length_b                   9.8662(3)
_cell_length_c                   18.2499(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.5660(10)
_cell_angle_gamma                90
_cell_volume                     2669.11(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5731
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      29.870
_cell_measurement_theta_min      2.317
_shelx_estimated_absorpt_T_max   0.814
_shelx_estimated_absorpt_T_min   0.480
_exptl_absorpt_coefficient_mu    1.433
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0608 before and 0.0337 after correction.
The Ratio of minimum to maximum transmission is 0.8458.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13351
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.317
_diffrn_ambient_temperature      120.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4842
_reflns_number_total             6074
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.563
_refine_diff_density_min         -0.928
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         6074
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.049
_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)+(0.0617P)²+1.1729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1296
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23),
  C24(H24), C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Se1 Se 0.62653(2) 0.57031(3) 0.53310(2) 0.04778(14) Uani 1 1 d . . . . .
N1 N 0.58159(15) 0.4176(2) 0.47957(14) 0.0343(5) Uani 1 1 d . . . . .
N2 N 0.73398(13) 0.36496(19) 0.52682(11) 0.0213(4) Uani 1 1 d . . . . .
N3 N 0.63417(14) 0.2056(2) 0.44826(12) 0.0274(5) Uani 1 1 d . . . . .
C1 C 0.64457(15) 0.3307(2) 0.48194(13) 0.0232(5) Uani 1 1 d . . . . .
C2 C 0.74100(17) 0.4933(3) 0.55529(15) 0.0298(6) Uani 1 1 d . . . . .
C3 C 0.82290(17) 0.5404(3) 0.60049(15) 0.0309(6) Uani 1 1 d . . . . .
H3 H 0.829353 0.631358 0.618168 0.037 Uiso 1 1 calc R U . . .
C4 C 0.89418(16) 0.4522(3) 0.61894(14) 0.0261(5) Uani 1 1 d . . . . .
H4 H 0.950896 0.482215 0.649757 0.031 Uiso 1 1 calc R U . . .
C5 C 0.88431(15) 0.3187(3) 0.59295(13) 0.0244(5) Uani 1 1 d . . . . .
H5 H 0.933684 0.257603 0.607531 0.029 Uiso 1 1 calc R U . . .
C6 C 0.80415(15) 0.2754(2) 0.54671(13) 0.0218(5) Uani 1 1 d . . . . .
H6 H 0.797171 0.184695 0.528632 0.026 Uiso 1 1 calc R U . . .
C7 C 0.68009(19) 0.1874(3) 0.38711(15) 0.0325(6) Uani 1 1 d . . . . .
H7A H 0.642941 0.226712 0.339711 0.049 Uiso 1 1 calc R U . . .
H7B H 0.688839 0.090462 0.379659 0.049 Uiso 1 1 calc R U . . .
H7C H 0.738830 0.232887 0.401557 0.049 Uiso 1 1 calc R U . . .
C8 C 0.54119(18) 0.1545(3) 0.42754(18) 0.0403(7) Uani 1 1 d . . . . .
H8A H 0.516060 0.162423 0.471341 0.060 Uiso 1 1 calc R U . . .
H8B H 0.540820 0.059203 0.412359 0.060 Uiso 1 1 calc R U . . .
H8C H 0.504581 0.207865 0.385084 0.060 Uiso 1 1 calc R U . . .
C9 C 0.77143(15) 0.7685(2) 0.73899(13) 0.0188(4) Uani 1 1 d . . . . .
C10 C 0.85461(16) 0.7047(2) 0.77252(13) 0.0224(5) Uani 1 1 d . . . . .
H10 H 0.907919 0.758193 0.784569 0.027 Uiso 1 1 calc R U . . .
C11 C 0.86173(17) 0.5676(2) 0.78856(15) 0.0262(5) Uani 1 1 d . . . . .
H11 H 0.919131 0.529232 0.811811 0.031 Uiso 1 1 calc R U . . .
C12 C 0.78602(18) 0.4860(2) 0.77105(16) 0.0294(6) Uani 1 1 d . . . . .
H12 H 0.790793 0.391714 0.782060 0.035 Uiso 1 1 calc R U . . .
C13 C 0.70327(17) 0.5439(2) 0.73723(16) 0.0292(6) Uani 1 1 d . . . . .
H13 H 0.650672 0.488908 0.724202 0.035 Uiso 1 1 calc R U . . .
C14 C 0.69646(15) 0.6827(2) 0.72209(14) 0.0226(5) Uani 1 1 d . . . . .
H14 H 0.638655 0.720347 0.699430 0.027 Uiso 1 1 calc R U . . .
C15 C 0.83797(14) 1.0130(2) 0.78613(13) 0.0190(4) Uani 1 1 d . . . . .
C16 C 0.88099(16) 1.1341(2) 0.77595(14) 0.0237(5) Uani 1 1 d . . . . .
H16 H 0.873413 1.167073 0.725716 0.028 Uiso 1 1 calc R U . . .
C17 C 0.93420(17) 1.2079(2) 0.83627(15) 0.0278(5) Uani 1 1 d . . . . .
H17 H 0.962653 1.288871 0.826661 0.033 Uiso 1 1 calc R U . . .
C18 C 0.94605(17) 1.1637(2) 0.91073(15) 0.0297(6) Uani 1 1 d . . . . .
H18 H 0.982436 1.213700 0.952217 0.036 Uiso 1 1 calc R U . . .
C19 C 0.90379(17) 1.0456(3) 0.92308(15) 0.0273(5) Uani 1 1 d . . . . .
H19 H 0.910602 1.014405 0.973558 0.033 Uiso 1 1 calc R U . . .
C20 C 0.85144(16) 0.9724(2) 0.86217(14) 0.0235(5) Uani 1 1 d . . . . .
H20 H 0.823493 0.891247 0.872322 0.028 Uiso 1 1 calc R U . . .
C21 C 0.79350(15) 0.9332(2) 0.63498(13) 0.0192(4) Uani 1 1 d . . . . .
C22 C 0.72762(17) 0.8981(2) 0.56759(14) 0.0253(5) Uani 1 1 d . . . . .
H22 H 0.667428 0.882832 0.569816 0.030 Uiso 1 1 calc R U . . .
C23 C 0.7478(2) 0.8849(3) 0.49775(15) 0.0336(6) Uani 1 1 d . . . . .
H23 H 0.701783 0.859765 0.453731 0.040 Uiso 1 1 calc R U . . .
C24 C 0.8346(2) 0.9084(3) 0.49251(16) 0.0357(7) Uani 1 1 d . . . . .
H24 H 0.848550 0.900133 0.445074 0.043 Uiso 1 1 calc R U . . .
C25 C 0.90015(19) 0.9439(3) 0.55692(16) 0.0319(6) Uani 1 1 d . . . . .
H25 H 0.959766 0.961474 0.553849 0.038 Uiso 1 1 calc R U . . .
C26 C 0.87996(16) 0.9543(2) 0.62692(14) 0.0233(5) Uani 1 1 d . . . . .
H26 H 0.927044 0.976773 0.670734 0.028 Uiso 1 1 calc R U . . .
C27 C 0.67066(14) 1.0037(2) 0.71074(13) 0.0189(4) Uani 1 1 d . . . . .
C28 C 0.62001(15) 0.9748(2) 0.76221(14) 0.0233(5) Uani 1 1 d . . . . .
H28 H 0.640173 0.904885 0.798590 0.028 Uiso 1 1 calc R U . . .
C29 C 0.54113(16) 1.0447(3) 0.76217(16) 0.0291(6) Uani 1 1 d . . . . .
H29 H 0.508507 1.021552 0.797813 0.035 Uiso 1 1 calc R U . . .
C30 C 0.51033(16) 1.1481(3) 0.70999(16) 0.0314(6) Uani 1 1 d . . . . .
H30 H 0.456137 1.195006 0.709048 0.038 Uiso 1 1 calc R U . . .
C31 C 0.55973(17) 1.1818(2) 0.65931(15) 0.0285(5) Uani 1 1 d . . . . .
H31 H 0.540346 1.253980 0.624245 0.034 Uiso 1 1 calc R U . . .
C32 C 0.63829(16) 1.1095(2) 0.65981(15) 0.0247(5) Uani 1 1 d . . . . .
H32 H 0.670772 1.133358 0.624182 0.030 Uiso 1 1 calc R U . . .
B1 B 0.76822(16) 0.9302(2) 0.71726(15) 0.0171(5) Uani 1 1 d . . . . .


_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 1.827(2) . ?
Se1 C2 1.860(2) . ?
N1 C1 1.286(3) . ?
N2 C1 1.440(3) . ?
N2 C2 1.362(3) . ?
N2 C6 1.367(3) . ?
N3 C1 1.370(3) . ?
N3 C7 1.483(3) . ?
N3 C8 1.467(3) . ?
C2 C3 1.388(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.370(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.363(3) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.410(3) . ?
C9 C14 1.397(3) . ?
C9 B1 1.642(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.396(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.403(3) . ?
C15 C20 1.405(3) . ?
C15 B1 1.635(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.392(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.411(3) . ?
C21 C26 1.393(3) . ?
C21 B1 1.649(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.396(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.384(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.373(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.397(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.401(3) . ?
C27 C32 1.398(3) . ?
C27 B1 1.642(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.396(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.389(4) . ?
C30 H30 0.9500 . ?
C30 C31 1.386(4) . ?
C31 H31 0.9500 . ?
C31 C32 1.402(3) . ?
C32 H32 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
N1 Se1 C2 88.87(10) . . ?
C1 N1 Se1 110.97(17) . . ?
C2 N2 C1 113.63(19) . . ?
C2 N2 C6 121.6(2) . . ?
C6 N2 C1 124.46(19) . . ?
C1 N3 C7 115.1(2) . . ?
C1 N3 C8 114.4(2) . . ?
C8 N3 C7 113.1(2) . . ?
N1 C1 N2 117.3(2) . . ?
N1 C1 N3 126.1(2) . . ?
N3 C1 N2 116.45(19) . . ?
N2 C2 Se1 108.85(17) . . ?
N2 C2 C3 120.3(2) . . ?
C3 C2 Se1 130.44(19) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.2(2) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5 119.9 . . ?
N2 C6 H6 120.6 . . ?
C5 C6 N2 118.8(2) . . ?
C5 C6 H6 120.6 . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 B1 120.2(2) . . ?
C14 C9 C10 115.2(2) . . ?
C14 C9 B1 124.5(2) . . ?
C9 C10 H10 118.7 . . ?
C11 C10 C9 122.7(2) . . ?
C11 C10 H10 118.7 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.8(2) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 H14 118.8 . . ?
C13 C14 C9 122.5(2) . . ?
C13 C14 H14 118.8 . . ?
C16 C15 C20 115.1(2) . . ?
C16 C15 B1 124.0(2) . . ?
C20 C15 B1 120.60(19) . . ?
C15 C16 H16 118.6 . . ?
C17 C16 C15 122.7(2) . . ?
C17 C16 H16 118.6 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.3(2) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.7 . . ?
C19 C18 C17 118.6(2) . . ?
C19 C18 H18 120.7 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 H20 118.6 . . ?
C19 C20 C15 122.9(2) . . ?
C19 C20 H20 118.6 . . ?
C22 C21 B1 120.0(2) . . ?
C26 C21 C22 115.3(2) . . ?
C26 C21 B1 124.3(2) . . ?
C21 C22 H22 118.8 . . ?
C23 C22 C21 122.3(2) . . ?
C23 C22 H22 118.8 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.2(3) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 120.5 . . ?
C25 C24 C23 119.0(2) . . ?
C25 C24 H24 120.5 . . ?
C24 C25 H25 119.7 . . ?
C24 C25 C26 120.6(3) . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 122.6(2) . . ?
C21 C26 H26 118.7 . . ?
C25 C26 H26 118.7 . . ?
C28 C27 B1 121.6(2) . . ?
C32 C27 C28 115.7(2) . . ?
C32 C27 B1 122.25(19) . . ?
C27 C28 H28 118.7 . . ?
C29 C28 C27 122.6(2) . . ?
C29 C28 H28 118.7 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 120.0(2) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 120.4 . . ?
C31 C30 C29 119.1(2) . . ?
C31 C30 H30 120.4 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 120.0(2) . . ?
C32 C31 H31 120.0 . . ?
C27 C32 C31 122.5(2) . . ?
C27 C32 H32 118.7 . . ?
C31 C32 H32 118.7 . . ?
C9 B1 C21 103.77(17) . . ?
C9 B1 C27 114.47(18) . . ?
C15 B1 C9 109.19(18) . . ?
C15 B1 C21 115.11(18) . . ?
C15 B1 C27 103.53(17) . . ?
C27 B1 C21 111.13(18) . . ?

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
Se1 N1 C1 N2 2.6(3) . . . . ?
Se1 N1 C1 N3 179.7(2) . . . . ?
Se1 C2 C3 C4 167.7(2) . . . . ?
N1 Se1 C2 N2 -4.0(2) . . . . ?
N1 Se1 C2 C3 -176.2(3) . . . . ?
N2 C2 C3 C4 -3.7(4) . . . . ?
C1 N2 C2 Se1 6.1(3) . . . . ?
C1 N2 C2 C3 179.2(2) . . . . ?
C1 N2 C6 C5 -176.4(2) . . . . ?
C2 Se1 N1 C1 0.8(2) . . . . ?
C2 N2 C1 N1 -6.0(3) . . . . ?
C2 N2 C1 N3 176.6(2) . . . . ?
C2 N2 C6 C5 -3.5(3) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C3 C4 C5 C6 2.1(4) . . . . ?
C4 C5 C6 N2 -0.3(3) . . . . ?
C6 N2 C1 N1 167.3(2) . . . . ?
C6 N2 C1 N3 -10.0(3) . . . . ?
C6 N2 C2 Se1 -167.46(18) . . . . ?
C6 N2 C2 C3 5.6(4) . . . . ?
C7 N3 C1 N1 115.2(3) . . . . ?
C7 N3 C1 N2 -67.6(3) . . . . ?
C8 N3 C1 N1 -18.4(4) . . . . ?
C8 N3 C1 N2 158.7(2) . . . . ?
C9 C10 C11 C12 0.8(4) . . . . ?
C10 C9 C14 C13 0.0(3) . . . . ?
C10 C9 B1 C15 -41.8(3) . . . . ?
C10 C9 B1 C21 81.4(2) . . . . ?
C10 C9 B1 C27 -157.3(2) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C12 C13 C14 C9 0.9(4) . . . . ?
C14 C9 C10 C11 -0.8(3) . . . . ?
C14 C9 B1 C15 142.7(2) . . . . ?
C14 C9 B1 C21 -94.1(2) . . . . ?
C14 C9 B1 C27 27.2(3) . . . . ?
C15 C16 C17 C18 -0.8(4) . . . . ?
C16 C15 C20 C19 -0.4(3) . . . . ?
C16 C15 B1 C9 152.1(2) . . . . ?
C16 C15 B1 C21 35.9(3) . . . . ?
C16 C15 B1 C27 -85.6(2) . . . . ?
C16 C17 C18 C19 -0.1(4) . . . . ?
C17 C18 C19 C20 0.6(4) . . . . ?
C18 C19 C20 C15 -0.4(4) . . . . ?
C20 C15 C16 C17 1.0(3) . . . . ?
C20 C15 B1 C9 -34.5(3) . . . . ?
C20 C15 B1 C21 -150.7(2) . . . . ?
C20 C15 B1 C27 87.8(2) . . . . ?
C21 C22 C23 C24 -0.9(4) . . . . ?
C22 C21 C26 C25 1.0(3) . . . . ?
C22 C21 B1 C9 77.7(2) . . . . ?
C22 C21 B1 C15 -163.04(19) . . . . ?
C22 C21 B1 C27 -45.8(3) . . . . ?
C22 C23 C24 C25 0.4(4) . . . . ?
C23 C24 C25 C26 0.9(4) . . . . ?
C24 C25 C26 C21 -1.6(4) . . . . ?
C26 C21 C22 C23 0.2(3) . . . . ?
C26 C21 B1 C9 -95.0(2) . . . . ?
C26 C21 B1 C15 24.3(3) . . . . ?
C26 C21 B1 C27 141.6(2) . . . . ?
C27 C28 C29 C30 -0.4(4) . . . . ?
C28 C27 C32 C31 -0.6(3) . . . . ?
C28 C27 B1 C9 40.4(3) . . . . ?
C28 C27 B1 C15 -78.3(2) . . . . ?
C28 C27 B1 C21 157.6(2) . . . . ?
C28 C29 C30 C31 -1.1(4) . . . . ?
C29 C30 C31 C32 1.7(4) . . . . ?
C30 C31 C32 C27 -0.9(4) . . . . ?
C32 C27 C28 C29 1.3(3) . . . . ?
C32 C27 B1 C9 -147.3(2) . . . . ?
C32 C27 B1 C15 93.9(2) . . . . ?
C32 C27 B1 C21 -30.2(3) . . . . ?
B1 C9 C10 C11 -176.8(2) . . . . ?
B1 C9 C14 C13 175.7(2) . . . . ?
B1 C15 C16 C17 174.7(2) . . . . ?
B1 C15 C20 C19 -174.3(2) . . . . ?
B1 C21 C22 C23 -173.1(2) . . . . ?
B1 C21 C26 C25 174.0(2) . . . . ?
B1 C27 C28 C29 174.0(2) . . . . ?
B1 C27 C32 C31 -173.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
