# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_ah56c
_database_code_depnum_ccdc_archive 'CCDC 2247957'
loop_
_audit_author_name
_audit_author_address
'Alexandre N. Sobolev'
;Centre for Microscopy Characterisation and Analysis The University of Western Australia
Australia
;
_audit_update_record             
;
2023-03-11 deposited with the CCDC.	2023-05-18 downloaded from the CCDC.
;

#==============================================================================

# 6. CRYSTALLOGRAPHY

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 N4 Se2, 2(C H Cl3)'
_chemical_formula_sum            'C24 H22 Cl6 N4 Se2'
_chemical_formula_weight         737.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.2960(2)
_cell_length_b                   19.9813(5)
_cell_length_c                   9.9038(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.675(2)
_cell_angle_gamma                90
_cell_volume                     1402.88(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7544
_cell_measurement_theta_min      2.338
_cell_measurement_theta_max      30.379
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0287597
_diffrn_orient_matrix_UB_12      -0.0273946
_diffrn_orient_matrix_UB_13      0.0356457
_diffrn_orient_matrix_UB_21      0.0006900
_diffrn_orient_matrix_UB_22      -0.0210927
_diffrn_orient_matrix_UB_23      -0.0574797
_diffrn_orient_matrix_UB_31      0.0958203
_diffrn_orient_matrix_UB_32      -0.0080595
_diffrn_orient_matrix_UB_33      0.0292916

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.172
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.044
_exptl_absorpt_coefficient_mu    3.230
_shelx_estimated_absorpt_T_min   0.607
_shelx_estimated_absorpt_T_max   0.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92245
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4738
_diffrn_reflns_number            29526
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.349
_diffrn_reflns_theta_max         32.685
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4884
_reflns_number_gt                3620
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2015/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4884
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.0936
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.29811(3) 0.47870(2) 0.17117(2) 0.02191(8) Uani 1 1 d . . . . .
C1 C 0.5099(3) 0.43977(11) 0.2817(2) 0.0160(4) Uani 1 1 d . . . . .
N2 N 0.5164(2) 0.38466(9) 0.36275(17) 0.0160(4) Uani 1 1 d . . . . .
C2 C 0.3555(3) 0.34246(11) 0.3674(2) 0.0183(4) Uani 1 1 d . . . . .
H2A H 0.390710 0.295135 0.357989 0.022 Uiso 1 1 calc R U . . .
H2B H 0.250744 0.353412 0.286883 0.022 Uiso 1 1 calc R U . . .
C3 C 0.7013(3) 0.37153(12) 0.4328(2) 0.0221(5) Uani 1 1 d . . . . .
H3 H 0.743031 0.335926 0.496142 0.026 Uiso 1 1 calc R U . . .
C4 C 0.8093(3) 0.41825(12) 0.3944(2) 0.0224(5) Uani 1 1 d . . . . .
H4 H 0.942363 0.422059 0.425596 0.027 Uiso 1 1 calc R U . . .
N5 N 0.6917(2) 0.46042(10) 0.30032(18) 0.0169(4) Uani 1 1 d . . . . .
C5 C 0.7550(3) 0.51721(11) 0.2313(2) 0.0195(4) Uani 1 1 d . . . . .
H5A H 0.667317 0.523365 0.139245 0.023 Uiso 1 1 calc R U . . .
H5B H 0.881066 0.506895 0.215598 0.023 Uiso 1 1 calc R U . . .
C21 C 0.2866(3) 0.34990(11) 0.4989(2) 0.0161(4) Uani 1 1 d . . . . .
C22 C 0.3076(3) 0.41025(11) 0.5724(2) 0.0158(4) Uani 1 1 d . . . . .
H22 H 0.373324 0.446321 0.542756 0.019 Uiso 1 1 calc R U . . .
C23 C 0.2332(3) 0.41808(12) 0.6886(2) 0.0181(4) Uani 1 1 d . . . . .
C24 C 0.1403(3) 0.36389(12) 0.7327(2) 0.0212(5) Uani 1 1 d . . . . .
H24 H 0.091046 0.368206 0.812853 0.025 Uiso 1 1 calc R U . . .
C25 C 0.1198(3) 0.30395(12) 0.6600(2) 0.0220(5) Uani 1 1 d . . . . .
H25 H 0.055890 0.267545 0.690189 0.026 Uiso 1 1 calc R U . . .
C26 C 0.1923(3) 0.29696(12) 0.5433(2) 0.0190(4) Uani 1 1 d . . . . .
H26 H 0.177458 0.255873 0.493684 0.023 Uiso 1 1 calc R U . . .
C10 C 0.3176(3) 0.64501(12) 0.0505(2) 0.0194(4) Uani 1 1 d . . . . .
H10 H 0.390359 0.603986 0.088270 0.023 Uiso 1 1 calc R U . . .
Cl11 Cl 0.09027(7) 0.62039(3) -0.04254(6) 0.02237(12) Uani 1 1 d . . . . .
Cl12 Cl 0.43858(9) 0.68642(3) -0.05927(6) 0.03004(15) Uani 1 1 d . . . . .
Cl13 Cl 0.30423(9) 0.69755(4) 0.19075(6) 0.03047(15) 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 C1 1.841(2) . ?
C1 N2 1.357(3) . ?
C1 N5 1.359(3) . ?
N2 C3 1.388(3) . ?
N2 C2 1.455(3) . ?
C2 C21 1.510(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.334(3) . ?
C3 H3 0.9500 . ?
C4 N5 1.391(3) . ?
C4 H4 0.9500 . ?
N5 C5 1.455(3) . ?
C5 C23 1.509(3) 3_666 ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C21 C26 1.389(3) . ?
C21 C22 1.398(3) . ?
C22 C23 1.392(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.401(3) . ?
C24 C25 1.387(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.386(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C10 Cl12 1.760(2) . ?
C10 Cl13 1.762(2) . ?
C10 Cl11 1.766(2) . ?
C10 H10 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N5 105.62(18) . . ?
N2 C1 Se1 126.98(16) . . ?
N5 C1 Se1 127.39(17) . . ?
C1 N2 C3 110.06(18) . . ?
C1 N2 C2 124.99(17) . . ?
C3 N2 C2 124.79(19) . . ?
N2 C2 C21 113.95(17) . . ?
N2 C2 H2A 108.8 . . ?
C21 C2 H2A 108.8 . . ?
N2 C2 H2B 108.8 . . ?
C21 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 N2 107.2(2) . . ?
C4 C3 H3 126.4 . . ?
N2 C3 H3 126.4 . . ?
C3 C4 N5 107.6(2) . . ?
C3 C4 H4 126.2 . . ?
N5 C4 H4 126.2 . . ?
C1 N5 C4 109.55(19) . . ?
C1 N5 C5 125.52(19) . . ?
C4 N5 C5 124.93(19) . . ?
N5 C5 C23 113.97(18) . 3_666 ?
N5 C5 H5A 108.8 . . ?
C23 C5 H5A 108.8 3_666 . ?
N5 C5 H5B 108.8 . . ?
C23 C5 H5B 108.8 3_666 . ?
H5A C5 H5B 107.7 . . ?
C26 C21 C22 119.57(19) . . ?
C26 C21 C2 119.3(2) . . ?
C22 C21 C2 121.07(19) . . ?
C23 C22 C21 120.8(2) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 118.8(2) . . ?
C22 C23 C5 123.1(2) . 3_666 ?
C24 C23 C5 118.06(19) . 3_666 ?
C25 C24 C23 120.4(2) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C24 120.3(2) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C21 120.2(2) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?
Cl12 C10 Cl13 109.64(12) . . ?
Cl12 C10 Cl11 110.79(12) . . ?
Cl13 C10 Cl11 110.92(12) . . ?
Cl12 C10 H10 108.5 . . ?
Cl13 C10 H10 108.5 . . ?
Cl11 C10 H10 108.5 . . ?

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
N5 C1 N2 C3 0.7(2) . . . . ?
Se1 C1 N2 C3 -178.73(16) . . . . ?
N5 C1 N2 C2 -174.87(18) . . . . ?
Se1 C1 N2 C2 5.7(3) . . . . ?
C1 N2 C2 C21 -107.5(2) . . . . ?
C3 N2 C2 C21 77.6(3) . . . . ?
C1 N2 C3 C4 -0.4(3) . . . . ?
C2 N2 C3 C4 175.18(19) . . . . ?
N2 C3 C4 N5 -0.1(3) . . . . ?
N2 C1 N5 C4 -0.7(2) . . . . ?
Se1 C1 N5 C4 178.68(16) . . . . ?
N2 C1 N5 C5 178.40(19) . . . . ?
Se1 C1 N5 C5 -2.2(3) . . . . ?
C3 C4 N5 C1 0.5(3) . . . . ?
C3 C4 N5 C5 -178.6(2) . . . . ?
C1 N5 C5 C23 92.1(2) . . . 3_666 ?
C4 N5 C5 C23 -88.9(3) . . . 3_666 ?
N2 C2 C21 C26 -154.05(19) . . . . ?
N2 C2 C21 C22 29.3(3) . . . . ?
C26 C21 C22 C23 -0.7(3) . . . . ?
C2 C21 C22 C23 175.93(19) . . . . ?
C21 C22 C23 C24 1.4(3) . . . . ?
C21 C22 C23 C5 -177.6(2) . . . 3_666 ?
C22 C23 C24 C25 -1.2(3) . . . . ?
C5 C23 C24 C25 177.8(2) 3_666 . . . ?
C23 C24 C25 C26 0.4(3) . . . . ?
C24 C25 C26 C21 0.3(3) . . . . ?
C22 C21 C26 C25 -0.1(3) . . . . ?
C2 C21 C26 C25 -176.83(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2B Se1 0.99 2.81 3.313(2) 112.3 . yes
C5 H5A Se1 0.99 3.14 3.913(2) 135.7 3_665 yes
C10 H10 Se1 1.00 2.77 3.546(2) 135.1 . yes

_refine_diff_density_max         0.559
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.107



####################################################################### 
# 
# 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_ah58c
_database_code_depnum_ccdc_archive 'CCDC 2247960'
loop_
_audit_author_name
_audit_author_address
'Alexandre N. Sobolev'
;Centre for Microscopy Characterisation and Analysis The University of Western Australia
Australia
;
_audit_update_record             
;
2023-03-11 deposited with the CCDC.	2023-05-18 downloaded from the CCDC.
;

#==============================================================================

# 6. CRYSTALLOGRAPHY

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H32 N4 Se2'
_chemical_formula_sum            'C28 H32 N4 Se2'
_chemical_formula_weight         582.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           57
_space_group_name_H-M_alt        'P b c m'
_space_group_name_Hall           '-P 2c 2b'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y-1/2, z'

_cell_length_a                   11.533(2)
_cell_length_b                   12.4756(13)
_cell_length_c                   17.2625(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2483.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1010
_cell_measurement_theta_min      3.827
_cell_measurement_theta_max      65.72

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    3.902
_shelx_estimated_absorpt_T_min   0.557
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.65825
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_detector_area_resol_mean 10.4738
_diffrn_reflns_number            11654
_diffrn_reflns_av_unetI/netI     0.1392
_diffrn_reflns_av_R_equivalents  0.1747
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.832
_diffrn_reflns_theta_max         67.361
_diffrn_reflns_theta_full        67.361
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2302
_reflns_number_gt                1112
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2015/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'X-Seed v. 4.0 (Barbour,m2001)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0890P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00023(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2302
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1498
_refine_ls_R_factor_gt           0.0738
_refine_ls_wR_factor_ref         0.2411
_refine_ls_wR_factor_gt          0.1780
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.70941(11) 0.47015(8) 0.05919(5) 0.0526(5) Uani 1 1 d . . . . .
N1 N 0.7160(8) 0.2468(6) 0.1018(4) 0.048(2) Uani 1 1 d . . . . .
C2 C 0.6500(11) 0.3373(7) 0.0878(5) 0.048(3) Uani 1 1 d . . . . .
N3 N 0.5389(8) 0.3117(6) 0.1025(4) 0.047(2) Uani 1 1 d . . . . .
C4 C 0.5320(12) 0.2045(8) 0.1229(5) 0.055(3) Uani 1 1 d . . . . .
H4 H 0.463095 0.165773 0.134087 0.066 Uiso 1 1 calc R U . . .
C5 C 0.6402(11) 0.1653(7) 0.1239(5) 0.047(3) Uani 1 1 d . . . . .
H5 H 0.661549 0.094125 0.137307 0.056 Uiso 1 1 calc R U . . .
C10 C 0.8419(10) 0.2401(8) 0.1052(5) 0.051(3) Uani 1 1 d . . . . .
H10A H 0.875510 0.313010 0.101891 0.061 Uiso 1 1 calc R U . . .
H10B H 0.870830 0.198018 0.060549 0.061 Uiso 1 1 calc R U . . .
C11 C 0.8535(14) 0.2376(11) 0.250000 0.049(4) Uani 1 2 d S T P . .
C12 C 0.8796(10) 0.1874(8) 0.1798(5) 0.051(3) Uani 1 1 d . . . . .
C13 C 0.9335(10) 0.0867(8) 0.1795(5) 0.050(3) Uani 1 1 d . . . . .
C14 C 0.9587(17) 0.0392(12) 0.250000 0.061(4) Uani 1 2 d S T P . .
H14 H 0.994907 -0.029175 0.250000 0.074 Uiso 1 2 calc R U P . .
C110 C 0.7940(16) 0.3451(11) 0.250000 0.056(4) Uani 1 2 d S T P . .
H11A H 0.782018 0.368855 0.196481 0.085 Uiso 0.5 1 calc R U P . .
H11B H 0.718821 0.338962 0.276136 0.085 Uiso 0.5 1 calc R U P . .
H11C H 0.842336 0.397386 0.277383 0.085 Uiso 0.5 1 calc R U P . .
C130 C 0.9597(11) 0.0288(9) 0.1050(5) 0.060(3) Uani 1 1 d . . . . .
H13A H 1.015239 0.070692 0.074540 0.090 Uiso 1 1 calc R U . . .
H13B H 0.887950 0.019640 0.075291 0.090 Uiso 1 1 calc R U . . .
H13C H 0.992905 -0.041691 0.116673 0.090 Uiso 1 1 calc R U . . .
C30 C 0.4398(10) 0.3851(8) 0.1048(5) 0.052(3) Uani 1 1 d . . . . .
H30A H 0.388334 0.371117 0.059975 0.063 Uiso 1 1 calc R U . . .
H30B H 0.467472 0.460035 0.101259 0.063 Uiso 1 1 calc R U . . .
C31 C 0.4233(16) 0.4034(11) 0.250000 0.056(4) Uani 1 2 d S T P . .
C32 C 0.3726(11) 0.3696(8) 0.1796(5) 0.051(3) Uani 1 1 d . . . . .
C33 C 0.2690(12) 0.3115(8) 0.1798(5) 0.058(3) Uani 1 1 d . . . . .
C34 C 0.2164(16) 0.2845(12) 0.250000 0.058(4) Uani 1 2 d S T P . .
H34 H 0.144334 0.247659 0.250000 0.070 Uiso 1 2 calc R U P . .
C310 C 0.5284(14) 0.4772(10) 0.250000 0.049(4) Uani 1 2 d S T P . .
H31A H 0.551608 0.492199 0.303518 0.073 Uiso 0.5 1 calc R U P . .
H31B H 0.592529 0.442417 0.222571 0.073 Uiso 0.5 1 calc R U P . .
H31C H 0.508585 0.544539 0.223911 0.073 Uiso 0.5 1 calc R U P . .
C330 C 0.2109(11) 0.2716(9) 0.1055(5) 0.058(3) Uani 1 1 d . . . . .
H33A H 0.197382 0.332388 0.070603 0.087 Uiso 1 1 calc R U . . .
H33B H 0.136660 0.237759 0.118263 0.087 Uiso 1 1 calc R U . . .
H33C H 0.261389 0.219304 0.079898 0.087 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C2 1.861(10) . ?
N1 C2 1.382(13) . ?
N1 C5 1.394(13) . ?
N1 C10 1.456(14) . ?
C2 N3 1.344(14) . ?
N3 C4 1.386(12) . ?
N3 C30 1.465(13) . ?
C4 C5 1.340(15) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C10 C12 1.511(14) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.397(12) 6_556 ?
C11 C12 1.397(12) . ?
C11 C110 1.51(2) . ?
C12 C13 1.402(14) . ?
C13 C14 1.385(12) . ?
C13 C130 1.505(13) . ?
C14 H14 0.9500 . ?
C110 H11A 0.9800 . ?
C110 H11B 0.9800 . ?
C110 H11C 0.9800 . ?
C110 H11A 0.9800 6_556 ?
C110 H11B 0.9799 6_556 ?
C110 H11C 0.9800 6_556 ?
C130 H13A 0.9800 . ?
C130 H13B 0.9800 . ?
C130 H13C 0.9800 . ?
C30 C32 1.519(14) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.412(13) . ?
C31 C32 1.412(13) 6_556 ?
C31 C310 1.52(2) . ?
C32 C33 1.398(17) . ?
C33 C34 1.396(14) . ?
C33 C330 1.531(14) . ?
C34 H34 0.9500 . ?
C310 H31A 0.9800 . ?
C310 H31B 0.9800 . ?
C310 H31C 0.9800 . ?
C310 H31A 0.9801 6_556 ?
C310 H31B 0.9800 6_556 ?
C310 H31C 0.9800 6_556 ?
C330 H33A 0.9800 . ?
C330 H33B 0.9800 . ?
C330 H33C 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
C2 N1 C5 107.3(9) . . ?
C2 N1 C10 127.1(9) . . ?
C5 N1 C10 124.9(9) . . ?
N3 C2 N1 107.4(8) . . ?
N3 C2 Se1 127.7(7) . . ?
N1 C2 Se1 124.8(9) . . ?
C2 N3 C4 109.3(9) . . ?
C2 N3 C30 126.9(8) . . ?
C4 N3 C30 123.5(10) . . ?
C5 C4 N3 107.6(11) . . ?
C5 C4 H4 126.2 . . ?
N3 C4 H4 126.2 . . ?
C4 C5 N1 108.3(9) . . ?
C4 C5 H5 125.9 . . ?
N1 C5 H5 125.9 . . ?
N1 C10 C12 110.2(8) . . ?
N1 C10 H10A 109.6 . . ?
C12 C10 H10A 109.6 . . ?
N1 C10 H10B 109.6 . . ?
C12 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 C12 120.3(13) 6_556 . ?
C12 C11 C110 119.8(7) 6_556 . ?
C12 C11 C110 119.8(7) . . ?
C11 C12 C13 120.1(9) . . ?
C11 C12 C10 118.9(10) . . ?
C13 C12 C10 120.9(8) . . ?
C14 C13 C12 118.2(9) . . ?
C14 C13 C130 120.2(10) . . ?
C12 C13 C130 121.5(9) . . ?
C13 C14 C13 123.1(13) . 6_556 ?
C13 C14 H14 118.5 . . ?
C13 C14 H14 118.5 6_556 . ?
C11 C110 H11A 109.5 . . ?
C11 C110 H11B 109.5 . . ?
H11A C110 H11B 109.5 . . ?
C11 C110 H11C 109.5 . . ?
H11A C110 H11C 109.5 . . ?
H11B C110 H11C 109.5 . . ?
C11 C110 H11A 109.471(13) . 6_556 ?
H11A C110 H11A 141.0 . 6_556 ?
H11B C110 H11A 57.7 . 6_556 ?
H11C C110 H11A 54.8 . 6_556 ?
C11 C110 H11B 109.5(8) . 6_556 ?
H11A C110 H11B 57.7 . 6_556 ?
H11B C110 H11B 54.8 . 6_556 ?
H11C C110 H11B 141.0 . 6_556 ?
H11A C110 H11B 109.5 6_556 6_556 ?
C11 C110 H11C 109.5(8) . 6_556 ?
H11A C110 H11C 54.8 . 6_556 ?
H11B C110 H11C 141.0 . 6_556 ?
H11C C110 H11C 57.7 . 6_556 ?
H11A C110 H11C 109.5 6_556 6_556 ?
H11B C110 H11C 109.5 6_556 6_556 ?
C13 C130 H13A 109.5 . . ?
C13 C130 H13B 109.5 . . ?
H13A C130 H13B 109.5 . . ?
C13 C130 H13C 109.5 . . ?
H13A C130 H13C 109.5 . . ?
H13B C130 H13C 109.5 . . ?
N3 C30 C32 110.0(8) . . ?
N3 C30 H30A 109.7 . . ?
C32 C30 H30A 109.7 . . ?
N3 C30 H30B 109.7 . . ?
C32 C30 H30B 109.7 . . ?
H30A C30 H30B 108.2 . . ?
C32 C31 C32 118.6(15) . 6_556 ?
C32 C31 C310 120.7(7) . . ?
C32 C31 C310 120.7(7) 6_556 . ?
C33 C32 C31 120.4(10) . . ?
C33 C32 C30 120.2(8) . . ?
C31 C32 C30 118.9(11) . . ?
C34 C33 C32 119.9(10) . . ?
C34 C33 C330 117.3(12) . . ?
C32 C33 C330 122.7(9) . . ?
C33 C34 C33 120.4(17) 6_556 . ?
C33 C34 H34 119.8 6_556 . ?
C33 C34 H34 119.8 . . ?
C31 C310 H31A 109.5 . . ?
C31 C310 H31B 109.5 . . ?
H31A C310 H31B 109.5 . . ?
C31 C310 H31C 109.5 . . ?
H31A C310 H31C 109.5 . . ?
H31B C310 H31C 109.5 . . ?
C31 C310 H31A 109.473(12) . 6_556 ?
H31A C310 H31A 141.0 . 6_556 ?
H31B C310 H31A 54.7 . 6_556 ?
H31C C310 H31A 57.8 . 6_556 ?
C31 C310 H31B 109.5(7) . 6_556 ?
H31A C310 H31B 54.7 . 6_556 ?
H31B C310 H31B 57.8 . 6_556 ?
H31C C310 H31B 141.0 . 6_556 ?
H31A C310 H31B 109.5 6_556 6_556 ?
C31 C310 H31C 109.5(7) . 6_556 ?
H31A C310 H31C 57.8 . 6_556 ?
H31B C310 H31C 141.0 . 6_556 ?
H31C C310 H31C 54.7 . 6_556 ?
H31A C310 H31C 109.5 6_556 6_556 ?
H31B C310 H31C 109.5 6_556 6_556 ?
C33 C330 H33A 109.5 . . ?
C33 C330 H33B 109.5 . . ?
H33A C330 H33B 109.5 . . ?
C33 C330 H33C 109.5 . . ?
H33A C330 H33C 109.5 . . ?
H33B C330 H33C 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
C5 N1 C2 N3 1.2(9) . . . . ?
C10 N1 C2 N3 -170.0(8) . . . . ?
C5 N1 C2 Se1 178.2(6) . . . . ?
C10 N1 C2 Se1 7.0(12) . . . . ?
N1 C2 N3 C4 -2.3(10) . . . . ?
Se1 C2 N3 C4 -179.2(6) . . . . ?
N1 C2 N3 C30 172.0(8) . . . . ?
Se1 C2 N3 C30 -4.9(13) . . . . ?
C2 N3 C4 C5 2.6(10) . . . . ?
C30 N3 C4 C5 -172.0(8) . . . . ?
N3 C4 C5 N1 -1.8(10) . . . . ?
C2 N1 C5 C4 0.4(9) . . . . ?
C10 N1 C5 C4 171.8(8) . . . . ?
C2 N1 C10 C12 127.4(9) . . . . ?
C5 N1 C10 C12 -42.4(12) . . . . ?
C12 C11 C12 C13 -1(2) 6_556 . . . ?
C110 C11 C12 C13 -179.1(13) . . . . ?
C12 C11 C12 C10 175.4(9) 6_556 . . . ?
C110 C11 C12 C10 -3(2) . . . . ?
N1 C10 C12 C11 -62.9(14) . . . . ?
N1 C10 C12 C13 113.1(11) . . . . ?
C11 C12 C13 C14 0.4(19) . . . . ?
C10 C12 C13 C14 -175.5(13) . . . . ?
C11 C12 C13 C130 178.1(12) . . . . ?
C10 C12 C13 C130 2.2(17) . . . . ?
C12 C13 C14 C13 0(3) . . . 6_556 ?
C130 C13 C14 C13 -177.9(11) . . . 6_556 ?
C2 N3 C30 C32 -128.8(9) . . . . ?
C4 N3 C30 C32 44.8(12) . . . . ?
C32 C31 C32 C33 5(2) 6_556 . . . ?
C310 C31 C32 C33 -173.0(11) . . . . ?
C32 C31 C32 C30 -167.1(9) 6_556 . . . ?
C310 C31 C32 C30 14.5(19) . . . . ?
N3 C30 C32 C33 -102.2(11) . . . . ?
N3 C30 C32 C31 70.3(13) . . . . ?
C31 C32 C33 C34 -1.4(18) . . . . ?
C30 C32 C33 C34 170.9(11) . . . . ?
C31 C32 C33 C330 -179.3(11) . . . . ?
C30 C32 C33 C330 -6.9(16) . . . . ?
C32 C33 C34 C33 -3(2) . . . 6_556 ?
C330 C33 C34 C33 175.4(9) . . . 6_556 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C30 H30A Se1 0.99 3.07 3.773(9) 129.0 5_665 yes
C30 H30B Se1 0.99 2.89 3.379(12) 111.6 . yes
C10 H10A Se1 0.99 2.84 3.347(10) 112.6 . yes

_refine_diff_density_max         1.024
_refine_diff_density_min         -1.013
_refine_diff_density_rms         0.128



####################################################################### 
# 
# 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_ah60c_180504_ndl
_database_code_depnum_ccdc_archive 'CCDC 2247958'
loop_
_audit_author_name
_audit_author_address
'Alexandre N. Sobolev'
;Centre for Microscopy Characterisation and Analysis The University of Western Australia
Australia
;
_audit_update_record             
;
2023-03-11 deposited with the CCDC.	2023-05-18 downloaded from the CCDC.
;

#==============================================================================

# 6. CRYSTALLOGRAPHY

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_weight         498.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.1187(2)
_cell_length_b                   14.2693(6)
_cell_length_c                   19.7393(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.384(4)
_cell_angle_gamma                90
_cell_volume                     1983.67(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2240
_cell_measurement_theta_min      3.822
_cell_measurement_theta_max      66.686
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0193699
_diffrn_orient_matrix_UB_12      0.0462104
_diffrn_orient_matrix_UB_13      0.0712331
_diffrn_orient_matrix_UB_21      -0.0450193
_diffrn_orient_matrix_UB_22      -0.0945228
_diffrn_orient_matrix_UB_23      0.0317087
_diffrn_orient_matrix_UB_31      0.2132089
_diffrn_orient_matrix_UB_32      -0.0241312
_diffrn_orient_matrix_UB_33      0.0120015
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    4.776
_shelx_estimated_absorpt_T_min   0.315
_shelx_estimated_absorpt_T_max   0.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87535
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_detector_area_resol_mean 10.4738
_diffrn_reflns_number            17396
_diffrn_reflns_av_unetI/netI     0.0857
_diffrn_reflns_av_R_equivalents  0.1204
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.837
_diffrn_reflns_theta_max         67.155
_diffrn_reflns_theta_full        67.155
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3530
_reflns_number_gt                2449
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2015/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'X-Seed v. 4.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0650P)²+11.7500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3530
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1651
_refine_ls_wR_factor_gt          0.1342
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 1.01022(10) 0.08942(6) 0.30589(4) 0.0253(2) Uani 1 1 d . . . . .
Se2 Se 0.37913(10) 0.26566(6) -0.02953(4) 0.0281(2) Uani 1 1 d . . . . .
C1 C 0.9097(11) -0.0540(5) 0.1686(4) 0.0253(16) Uani 1 1 d . . . . .
H1A H 0.884572 -0.119258 0.152802 0.030 Uiso 1 1 calc R U . . .
H1B H 1.036013 -0.051615 0.197190 0.030 Uiso 1 1 calc R U . . .
C2 C 0.8228(10) 0.2198(5) -0.0524(4) 0.0237(15) Uani 1 1 d . . . . .
H2A H 0.937084 0.227649 -0.074986 0.028 Uiso 1 1 calc R U . . .
H2B H 0.716646 0.199931 -0.087534 0.028 Uiso 1 1 calc R U . . .
C3 C 0.5005(10) 0.4352(5) 0.0843(4) 0.0260(16) Uani 1 1 d . . . . .
H3A H 0.369787 0.435009 0.058934 0.031 Uiso 1 1 calc R U . . .
H3B H 0.530507 0.499950 0.100449 0.031 Uiso 1 1 calc R U . . .
C4 C 0.5589(10) 0.1568(5) 0.3019(4) 0.0240(15) Uani 1 1 d . . . . .
H4A H 0.660260 0.170493 0.340598 0.029 Uiso 1 1 calc R U . . .
H4B H 0.438445 0.147399 0.320544 0.029 Uiso 1 1 calc R U . . .
C11 C 0.7838(9) 0.0453(5) 0.2580(4) 0.0204(14) Uani 1 1 d . . . . .
N12 N 0.7605(8) -0.0217(4) 0.2084(3) 0.0219(13) Uani 1 1 d . . . . .
C13 C 0.5702(10) -0.0370(5) 0.1876(4) 0.0250(16) Uani 1 1 d . . . . .
H13 H 0.517438 -0.081066 0.154047 0.030 Uiso 1 1 calc R U . . .
C14 C 0.4718(10) 0.0207(6) 0.2228(4) 0.0283(17) Uani 1 1 d . . . . .
H14 H 0.337573 0.025645 0.218919 0.034 Uiso 1 1 calc R U . . .
N15 N 0.6064(8) 0.0723(4) 0.2663(3) 0.0228(13) Uani 1 1 d . . . . .
C21 C 0.6039(10) 0.3280(5) -0.0019(4) 0.0228(15) Uani 1 1 d . . . . .
N22 N 0.6322(8) 0.4069(4) 0.0388(3) 0.0227(13) Uani 1 1 d . . . . .
C23 C 0.8205(10) 0.4337(5) 0.0430(4) 0.0224(15) Uani 1 1 d . . . . .
H23 H 0.878276 0.484890 0.068867 0.027 Uiso 1 1 calc R U . . .
C24 C 0.9070(10) 0.3756(5) 0.0047(4) 0.0234(15) Uani 1 1 d . . . . .
H24 H 1.035880 0.379345 -0.002395 0.028 Uiso 1 1 calc R U . . .
N25 N 0.7760(8) 0.3084(4) -0.0231(3) 0.0214(13) Uani 1 1 d . . . . .
C111 C 0.9034(10) 0.0118(5) 0.1078(4) 0.0258(16) Uani 1 1 d . . . . .
C112 C 1.0085(10) 0.0945(5) 0.1133(4) 0.0253(16) Uani 1 1 d . . . . .
H112 H 1.097483 0.105413 0.153261 0.030 Uiso 1 1 calc R U . . .
C113 C 0.9863(10) 0.1606(5) 0.0623(4) 0.0241(15) Uani 1 1 d . . . . .
H113 H 1.056959 0.217266 0.067693 0.029 Uiso 1 1 calc R U . . .
C114 C 0.8598(10) 0.1446(5) 0.0024(4) 0.0218(15) Uani 1 1 d . . . . .
C115 C 0.7581(10) 0.0613(5) -0.0049(4) 0.0251(16) Uani 1 1 d . . . . .
H115 H 0.671723 0.050087 -0.045507 0.030 Uiso 1 1 calc R U . . .
C116 C 0.7816(10) -0.0062(5) 0.0471(4) 0.0255(16) Uani 1 1 d . . . . .
H116 H 0.715050 -0.064031 0.041136 0.031 Uiso 1 1 calc R U . . .
C121 C 0.5105(11) 0.3698(5) 0.1458(4) 0.0241(16) Uani 1 1 d . . . . .
C122 C 0.6882(10) 0.3456(5) 0.1824(4) 0.0244(16) Uani 1 1 d . . . . .
H122 H 0.800296 0.374324 0.171295 0.029 Uiso 1 1 calc R U . . .
C123 C 0.6999(10) 0.2808(5) 0.2339(4) 0.0237(16) Uani 1 1 d . . . . .
H123 H 0.820984 0.264600 0.257995 0.028 Uiso 1 1 calc R U . . .
C124 C 0.5388(10) 0.2380(5) 0.2518(4) 0.0237(15) Uani 1 1 d . . . . .
C125 C 0.3626(10) 0.2650(5) 0.2183(4) 0.0255(16) Uani 1 1 d . . . . .
H125 H 0.250487 0.239299 0.231656 0.031 Uiso 1 1 calc R U . . .
C126 C 0.3493(10) 0.3297(5) 0.1650(4) 0.0255(16) Uani 1 1 d . . . . .
H126 H 0.227911 0.346546 0.141573 0.031 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C11 1.855(7) . ?
Se2 C21 1.842(7) . ?
C1 N12 1.484(9) . ?
C1 C111 1.520(10) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N25 1.449(9) . ?
C2 C114 1.518(10) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N22 1.447(9) . ?
C3 C121 1.526(10) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N15 1.460(9) . ?
C4 C124 1.516(10) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C11 N15 1.353(9) . ?
C11 N12 1.362(9) . ?
N12 C13 1.374(9) . ?
C13 C14 1.338(11) . ?
C13 H13 0.9500 . ?
C14 N15 1.399(10) . ?
C14 H14 0.9500 . ?
C21 N25 1.380(9) . ?
C21 N22 1.380(9) . ?
N22 C23 1.385(9) . ?
C23 C24 1.331(11) . ?
C23 H23 0.9500 . ?
C24 N25 1.393(9) . ?
C24 H24 0.9500 . ?
C111 C112 1.393(11) . ?
C111 C116 1.396(11) . ?
C112 C113 1.372(11) . ?
C112 H112 0.9500 . ?
C113 C114 1.396(10) . ?
C113 H113 0.9500 . ?
C114 C115 1.388(11) . ?
C115 C116 1.400(11) . ?
C115 H115 0.9500 . ?
C116 H116 0.9500 . ?
C121 C126 1.383(11) . ?
C121 C122 1.405(10) . ?
C122 C123 1.369(10) . ?
C122 H122 0.9500 . ?
C123 C124 1.390(11) . ?
C123 H123 0.9500 . ?
C124 C125 1.385(10) . ?
C125 C126 1.391(11) . ?
C125 H125 0.9500 . ?
C126 H126 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
N12 C1 C111 106.6(6) . . ?
N12 C1 H1A 110.4 . . ?
C111 C1 H1A 110.4 . . ?
N12 C1 H1B 110.4 . . ?
C111 C1 H1B 110.4 . . ?
H1A C1 H1B 108.6 . . ?
N25 C2 C114 111.0(6) . . ?
N25 C2 H2A 109.4 . . ?
C114 C2 H2A 109.4 . . ?
N25 C2 H2B 109.4 . . ?
C114 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N22 C3 C121 111.3(6) . . ?
N22 C3 H3A 109.4 . . ?
C121 C3 H3A 109.4 . . ?
N22 C3 H3B 109.4 . . ?
C121 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
N15 C4 C124 108.8(6) . . ?
N15 C4 H4A 109.9 . . ?
C124 C4 H4A 109.9 . . ?
N15 C4 H4B 109.9 . . ?
C124 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
N15 C11 N12 105.6(6) . . ?
N15 C11 Se1 126.8(5) . . ?
N12 C11 Se1 127.6(5) . . ?
C11 N12 C13 109.7(6) . . ?
C11 N12 C1 125.3(6) . . ?
C13 N12 C1 122.9(6) . . ?
C14 C13 N12 108.4(7) . . ?
C14 C13 H13 125.8 . . ?
N12 C13 H13 125.8 . . ?
C13 C14 N15 106.2(6) . . ?
C13 C14 H14 126.9 . . ?
N15 C14 H14 126.9 . . ?
C11 N15 C14 110.1(6) . . ?
C11 N15 C4 125.4(6) . . ?
C14 N15 C4 123.0(6) . . ?
N25 C21 N22 106.3(6) . . ?
N25 C21 Se2 125.7(5) . . ?
N22 C21 Se2 127.8(5) . . ?
C21 N22 C23 108.5(6) . . ?
C21 N22 C3 122.4(6) . . ?
C23 N22 C3 126.5(6) . . ?
C24 C23 N22 108.5(6) . . ?
C24 C23 H23 125.7 . . ?
N22 C23 H23 125.7 . . ?
C23 C24 N25 108.3(6) . . ?
C23 C24 H24 125.9 . . ?
N25 C24 H24 125.9 . . ?
C21 N25 C24 108.3(6) . . ?
C21 N25 C2 124.3(6) . . ?
C24 N25 C2 125.3(6) . . ?
C112 C111 C116 118.8(7) . . ?
C112 C111 C1 120.5(7) . . ?
C116 C111 C1 120.5(7) . . ?
C113 C112 C111 121.5(7) . . ?
C113 C112 H112 119.3 . . ?
C111 C112 H112 119.3 . . ?
C112 C113 C114 120.0(7) . . ?
C112 C113 H113 120.0 . . ?
C114 C113 H113 120.0 . . ?
C115 C114 C113 119.3(7) . . ?
C115 C114 C2 119.8(6) . . ?
C113 C114 C2 120.7(7) . . ?
C114 C115 C116 120.6(7) . . ?
C114 C115 H115 119.7 . . ?
C116 C115 H115 119.7 . . ?
C111 C116 C115 119.7(7) . . ?
C111 C116 H116 120.2 . . ?
C115 C116 H116 120.2 . . ?
C126 C121 C122 118.6(7) . . ?
C126 C121 C3 121.8(7) . . ?
C122 C121 C3 119.5(7) . . ?
C123 C122 C121 120.0(7) . . ?
C123 C122 H122 120.0 . . ?
C121 C122 H122 120.0 . . ?
C122 C123 C124 121.5(6) . . ?
C122 C123 H123 119.2 . . ?
C124 C123 H123 119.2 . . ?
C125 C124 C123 118.7(7) . . ?
C125 C124 C4 121.2(7) . . ?
C123 C124 C4 119.9(6) . . ?
C124 C125 C126 120.2(7) . . ?
C124 C125 H125 119.9 . . ?
C126 C125 H125 119.9 . . ?
C121 C126 C125 120.9(7) . . ?
C121 C126 H126 119.6 . . ?
C125 C126 H126 119.6 . . ?

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
N15 C11 N12 C13 -1.4(8) . . . . ?
Se1 C11 N12 C13 177.6(5) . . . . ?
N15 C11 N12 C1 162.6(6) . . . . ?
Se1 C11 N12 C1 -18.4(10) . . . . ?
C111 C1 N12 C11 -86.9(8) . . . . ?
C111 C1 N12 C13 75.1(8) . . . . ?
C11 N12 C13 C14 1.0(8) . . . . ?
C1 N12 C13 C14 -163.4(6) . . . . ?
N12 C13 C14 N15 -0.2(8) . . . . ?
N12 C11 N15 C14 1.3(8) . . . . ?
Se1 C11 N15 C14 -177.7(5) . . . . ?
N12 C11 N15 C4 -165.0(6) . . . . ?
Se1 C11 N15 C4 16.0(10) . . . . ?
C13 C14 N15 C11 -0.7(8) . . . . ?
C13 C14 N15 C4 165.9(6) . . . . ?
C124 C4 N15 C11 86.6(8) . . . . ?
C124 C4 N15 C14 -78.0(8) . . . . ?
N25 C21 N22 C23 -1.0(8) . . . . ?
Se2 C21 N22 C23 -176.1(5) . . . . ?
N25 C21 N22 C3 -164.0(6) . . . . ?
Se2 C21 N22 C3 20.9(10) . . . . ?
C121 C3 N22 C21 71.9(8) . . . . ?
C121 C3 N22 C23 -87.9(9) . . . . ?
C21 N22 C23 C24 1.8(8) . . . . ?
C3 N22 C23 C24 163.9(7) . . . . ?
N22 C23 C24 N25 -1.8(8) . . . . ?
N22 C21 N25 C24 -0.1(8) . . . . ?
Se2 C21 N25 C24 175.1(5) . . . . ?
N22 C21 N25 C2 164.1(6) . . . . ?
Se2 C21 N25 C2 -20.6(10) . . . . ?
C23 C24 N25 C21 1.2(8) . . . . ?
C23 C24 N25 C2 -162.8(6) . . . . ?
C114 C2 N25 C21 -74.5(8) . . . . ?
C114 C2 N25 C24 87.1(8) . . . . ?
N12 C1 C111 C112 87.8(8) . . . . ?
N12 C1 C111 C116 -87.5(8) . . . . ?
C116 C111 C112 C113 3.9(11) . . . . ?
C1 C111 C112 C113 -171.4(7) . . . . ?
C111 C112 C113 C114 -1.7(11) . . . . ?
C112 C113 C114 C115 -0.3(11) . . . . ?
C112 C113 C114 C2 175.6(6) . . . . ?
N25 C2 C114 C115 124.9(7) . . . . ?
N25 C2 C114 C113 -50.9(9) . . . . ?
C113 C114 C115 C116 0.0(10) . . . . ?
C2 C114 C115 C116 -175.9(6) . . . . ?
C112 C111 C116 C115 -4.2(11) . . . . ?
C1 C111 C116 C115 171.2(7) . . . . ?
C114 C115 C116 C111 2.3(11) . . . . ?
N22 C3 C121 C126 -129.3(7) . . . . ?
N22 C3 C121 C122 47.7(9) . . . . ?
C126 C121 C122 C123 2.7(11) . . . . ?
C3 C121 C122 C123 -174.4(7) . . . . ?
C121 C122 C123 C124 -0.5(11) . . . . ?
C122 C123 C124 C125 -2.6(11) . . . . ?
C122 C123 C124 C4 171.2(7) . . . . ?
N15 C4 C124 C125 96.3(8) . . . . ?
N15 C4 C124 C123 -77.4(8) . . . . ?
C123 C124 C125 C126 3.7(11) . . . . ?
C4 C124 C125 C126 -170.1(7) . . . . ?
C122 C121 C126 C125 -1.6(11) . . . . ?
C3 C121 C126 C125 175.4(7) . . . . ?
C124 C125 C126 C121 -1.6(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H4B Se1 0.99 3.13 4.034(7) 152.4 1_455 yes
C23 H23 Se1 0.95 2.90 3.773(7) 153.9 2_755 yes
C24 H24 Se2 0.95 3.04 3.857(7) 144.4 1_655 yes

_refine_diff_density_max         1.171
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.161



####################################################################### 
# 
# 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_ah60c_180504
_database_code_depnum_ccdc_archive 'CCDC 2247961'
loop_
_audit_author_name
_audit_author_address
'Alexandre N. Sobolev'
;Centre for Microscopy Characterisation and Analysis The University of Western Australia
Australia
;
_audit_update_record             
;
2023-03-11 deposited with the CCDC.	2023-05-18 downloaded from the CCDC.
;

#==============================================================================

# 6. CRYSTALLOGRAPHY

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 N4 Se2'
_chemical_formula_sum            'C22 H20 N4 Se2'
_chemical_formula_weight         498.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1890(4)
_cell_length_b                   12.1051(4)
_cell_length_c                   9.9941(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.539(5)
_cell_angle_gamma                90
_cell_volume                     1011.27(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2641
_cell_measurement_theta_min      2.499
_cell_measurement_theta_max      30.907
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0032215
_diffrn_orient_matrix_UB_12      0.0580678
_diffrn_orient_matrix_UB_13      0.0080776
_diffrn_orient_matrix_UB_21      0.0846456
_diffrn_orient_matrix_UB_22      0.0018122
_diffrn_orient_matrix_UB_23      0.0367922
_diffrn_orient_matrix_UB_31      0.0049018
_diffrn_orient_matrix_UB_32      0.0078631
_diffrn_orient_matrix_UB_33      -0.0683125

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.034
_exptl_absorpt_coefficient_mu    3.671
_shelx_estimated_absorpt_T_min   0.527
_shelx_estimated_absorpt_T_max   0.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75572
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur-S'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0009
_diffrn_reflns_number            10805
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.802
_diffrn_reflns_theta_max         32.288
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3329
_reflns_number_gt                2408
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2015/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'X-Seed v. 4.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²+0.5700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3329
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1255
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.70245(4) 0.49134(3) 0.91147(3) 0.02151(12) Uani 1 1 d . . . . .
C1 C 0.6972(4) 0.3732(3) 0.7923(3) 0.0198(6) Uani 1 1 d . . . . .
N2 N 0.8075(3) 0.3484(2) 0.7391(3) 0.0207(5) Uani 1 1 d . . . . .
C2 C 0.9315(4) 0.4246(3) 0.7384(4) 0.0227(6) Uani 1 1 d . . . . .
H2A H 1.019088 0.382302 0.729294 0.027 Uiso 1 1 calc R U . . .
H2B H 0.976766 0.466210 0.832173 0.027 Uiso 1 1 calc R U . . .
C3 C 0.7653(4) 0.2513(3) 0.6575(3) 0.0232(7) Uani 1 1 d . . . . .
H3 H 0.822407 0.216696 0.608574 0.028 Uiso 1 1 calc R U . . .
C4 C 0.6281(4) 0.2157(3) 0.6610(3) 0.0221(6) Uani 1 1 d . . . . .
H4 H 0.570076 0.151299 0.614476 0.026 Uiso 1 1 calc R U . . .
N5 N 0.5871(3) 0.2899(2) 0.7445(3) 0.0196(5) Uani 1 1 d . . . . .
C5 C 0.4315(4) 0.2899(3) 0.7541(3) 0.0222(6) Uani 1 1 d . . . . .
H5A H 0.443352 0.322390 0.848985 0.027 Uiso 1 1 calc R U . . .
H5B H 0.392378 0.213166 0.749173 0.027 Uiso 1 1 calc R U . . .
C21 C 0.8600(4) 0.5045(3) 0.6108(4) 0.0206(6) Uani 1 1 d . . . . .
C22 C 0.8341(4) 0.6145(3) 0.6343(4) 0.0230(7) Uani 1 1 d . . . . .
H22 H 0.874719 0.642606 0.731808 0.028 Uiso 1 1 calc R U . . .
C23 C 0.7487(4) 0.6841(3) 0.5159(3) 0.0222(6) Uani 1 1 d . . . . .
H23 H 0.732415 0.759326 0.533149 0.027 Uiso 1 1 calc R U . . .
C24 C 0.6873(4) 0.6432(3) 0.3720(3) 0.0202(6) Uani 1 1 d . . . . .
C25 C 0.7228(4) 0.5353(3) 0.3489(4) 0.0241(7) Uani 1 1 d . . . . .
H25 H 0.687777 0.508111 0.251309 0.029 Uiso 1 1 calc R U . . .
C26 C 0.8092(4) 0.4667(3) 0.4669(4) 0.0230(6) Uani 1 1 d . . . . .
H26 H 0.833725 0.393461 0.449160 0.028 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C1 1.849(3) . ?
C1 N2 1.359(4) . ?
C1 N5 1.366(4) . ?
N2 C3 1.391(4) . ?
N2 C2 1.468(4) . ?
C2 C21 1.516(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.347(5) . ?
C3 H3 0.9500 . ?
C4 N5 1.380(4) . ?
C4 H4 0.9500 . ?
N5 C5 1.472(4) . ?
C5 C24 1.514(4) 3_666 ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C21 C22 1.389(4) . ?
C21 C26 1.392(5) . ?
C22 C23 1.399(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.399(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.388(5) . ?
C25 C26 1.390(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N5 105.3(3) . . ?
N2 C1 Se1 126.8(2) . . ?
N5 C1 Se1 127.8(2) . . ?
C1 N2 C3 110.1(3) . . ?
C1 N2 C2 124.7(3) . . ?
C3 N2 C2 123.8(3) . . ?
N2 C2 C21 109.8(3) . . ?
N2 C2 H2A 109.7 . . ?
C21 C2 H2A 109.7 . . ?
N2 C2 H2B 109.7 . . ?
C21 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C4 C3 N2 106.9(3) . . ?
C4 C3 H3 126.5 . . ?
N2 C3 H3 126.5 . . ?
C3 C4 N5 107.5(3) . . ?
C3 C4 H4 126.2 . . ?
N5 C4 H4 126.2 . . ?
C1 N5 C4 110.1(3) . . ?
C1 N5 C5 125.1(3) . . ?
C4 N5 C5 123.8(3) . . ?
N5 C5 C24 109.3(2) . 3_666 ?
N5 C5 H5A 109.8 . . ?
C24 C5 H5A 109.8 3_666 . ?
N5 C5 H5B 109.8 . . ?
C24 C5 H5B 109.8 3_666 . ?
H5A C5 H5B 108.3 . . ?
C22 C21 C26 118.8(3) . . ?
C22 C21 C2 120.9(3) . . ?
C26 C21 C2 120.2(3) . . ?
C21 C22 C23 120.6(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C24 120.1(3) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 118.8(3) . . ?
C25 C24 C5 120.2(3) . 3_666 ?
C23 C24 C5 120.6(3) . 3_666 ?
C24 C25 C26 120.8(3) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C25 C26 C21 120.6(3) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?

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
N5 C1 N2 C3 0.7(3) . . . . ?
Se1 C1 N2 C3 178.1(2) . . . . ?
N5 C1 N2 C2 167.8(3) . . . . ?
Se1 C1 N2 C2 -14.9(4) . . . . ?
C1 N2 C2 C21 -79.8(4) . . . . ?
C3 N2 C2 C21 85.5(3) . . . . ?
C1 N2 C3 C4 -0.3(3) . . . . ?
C2 N2 C3 C4 -167.4(3) . . . . ?
N2 C3 C4 N5 -0.3(3) . . . . ?
N2 C1 N5 C4 -0.9(3) . . . . ?
Se1 C1 N5 C4 -178.2(2) . . . . ?
N2 C1 N5 C5 -169.4(3) . . . . ?
Se1 C1 N5 C5 13.3(4) . . . . ?
C3 C4 N5 C1 0.8(3) . . . . ?
C3 C4 N5 C5 169.5(3) . . . . ?
C1 N5 C5 C24 81.0(3) . . . 3_666 ?
C4 N5 C5 C24 -86.0(3) . . . 3_666 ?
N2 C2 C21 C22 107.3(3) . . . . ?
N2 C2 C21 C26 -68.4(4) . . . . ?
C26 C21 C22 C23 4.4(5) . . . . ?
C2 C21 C22 C23 -171.3(3) . . . . ?
C21 C22 C23 C24 0.5(5) . . . . ?
C22 C23 C24 C25 -4.8(5) . . . . ?
C22 C23 C24 C5 168.1(3) . . . 3_666 ?
C23 C24 C25 C26 4.1(5) . . . . ?
C5 C24 C25 C26 -168.7(3) 3_666 . . . ?
C24 C25 C26 C21 0.8(5) . . . . ?
C22 C21 C26 C25 -5.1(5) . . . . ?
C2 C21 C26 C25 170.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2B Se1 0.99 3.04 3.849(3) 139.7 3_767 yes
C3 H3 Se1 0.95 3.10 3.718(3) 123.9 4_565 yes
C4 H4 Se1 0.95 3.09 3.912(3) 145.7 2_646 yes
C5 H5B Se1 0.99 3.06 3.953(3) 150.1 2_646 yes

_refine_diff_density_max         0.946
_refine_diff_density_min         -1.254
_refine_diff_density_rms         0.141



####################################################################### 
# 
# 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_ah54c
_database_code_depnum_ccdc_archive 'CCDC 2247962'
loop_
_audit_author_name
_audit_author_address
'Alexandre N. Sobolev'
;Centre for Microscopy Characterisation and Analysis The University of Western Australia
Australia
;
_audit_update_record             
;
2023-03-11 deposited with the CCDC.	2023-05-18 downloaded from the CCDC.
;

#==============================================================================

# 6. CRYSTALLOGRAPHY

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_weight         498.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   17.8415(4)
_cell_length_b                   10.5984(3)
_cell_length_c                   20.8127(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.348(2)
_cell_angle_gamma                90
_cell_volume                     3871.49(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3510
_cell_measurement_theta_min      4.322
_cell_measurement_theta_max      66.78
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0476920
_diffrn_orient_matrix_UB_12      0.0245211
_diffrn_orient_matrix_UB_13      -0.0682413
_diffrn_orient_matrix_UB_21      0.0493479
_diffrn_orient_matrix_UB_22      0.1162556
_diffrn_orient_matrix_UB_23      -0.0077451
_diffrn_orient_matrix_UB_31      0.0546423
_diffrn_orient_matrix_UB_32      -0.0836807
_diffrn_orient_matrix_UB_33      -0.0308787
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_F_000             1984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.092
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.013
_exptl_absorpt_coefficient_mu    4.894
_shelx_estimated_absorpt_T_min   0.662
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91795
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_detector_area_resol_mean 10.4738
_diffrn_reflns_number            19568
_diffrn_reflns_av_unetI/netI     0.0840
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.599
_diffrn_reflns_theta_max         67.249
_diffrn_reflns_theta_full        67.249
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             6875
_reflns_number_gt                4508
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2015/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0425P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6875
_refine_ls_number_parameters     505
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se11 Se 0.59360(4) 1.06313(6) 0.10415(3) 0.02824(17) Uani 1 1 d . . . . .
Se12 Se 0.77442(3) 0.84850(6) 0.14830(3) 0.02352(16) Uani 1 1 d . . . . .
C11 C 0.4736(3) 0.8204(6) 0.0833(3) 0.0258(13) Uani 1 1 d . . . . .
H11A H 0.503475 0.855828 0.051855 0.031 Uiso 1 1 calc R U . . .
H11B H 0.420162 0.848741 0.070148 0.031 Uiso 1 1 calc R U . . .
C12 C 0.6474(3) 1.0257(6) 0.2644(3) 0.0200(11) Uani 1 1 d . . . . .
H12A H 0.635209 1.116884 0.263923 0.024 Uiso 1 1 calc R U . . .
H12B H 0.690706 1.014160 0.241175 0.024 Uiso 1 1 calc R U . . .
C13 C 0.7736(3) 0.8317(6) 0.3070(3) 0.0218(12) Uani 1 1 d . . . . .
H13A H 0.796914 0.896605 0.282591 0.026 Uiso 1 1 calc R U . . .
H13B H 0.815109 0.779169 0.331412 0.026 Uiso 1 1 calc R U . . .
C14 C 0.6221(3) 0.6719(6) 0.1004(3) 0.0227(12) Uani 1 1 d . . . . .
H14A H 0.657301 0.622177 0.078689 0.027 Uiso 1 1 calc R U . . .
H14B H 0.617359 0.757138 0.080636 0.027 Uiso 1 1 calc R U . . .
N111 N 0.5042(3) 0.8688(5) 0.1493(2) 0.0200(10) Uani 1 1 d . . . . .
C112 C 0.5602(3) 0.9554(6) 0.1630(3) 0.0205(12) Uani 1 1 d . . . . .
N113 N 0.5807(3) 0.9564(5) 0.2290(2) 0.0212(10) Uani 1 1 d . . . . .
C114 C 0.5333(3) 0.8763(6) 0.2561(3) 0.0211(12) Uani 1 1 d . . . . .
H114 H 0.534143 0.862768 0.301358 0.025 Uiso 1 1 calc R U . . .
C115 C 0.4857(3) 0.8213(6) 0.2065(3) 0.0242(12) Uani 1 1 d . . . . .
H115 H 0.446995 0.761566 0.209952 0.029 Uiso 1 1 calc R U . . .
C121 C 0.6711(3) 0.9829(6) 0.3345(3) 0.0202(12) Uani 1 1 d . . . . .
C122 C 0.7307(3) 0.8954(5) 0.3547(3) 0.0176(11) Uani 1 1 d . . . . .
C123 C 0.7499(3) 0.8662(6) 0.4206(3) 0.0229(12) Uani 1 1 d . . . . .
H123 H 0.790893 0.809576 0.434509 0.028 Uiso 1 1 calc R U . . .
C124 C 0.7117(3) 0.9166(6) 0.4666(3) 0.0230(12) Uani 1 1 d . . . . .
H124 H 0.726449 0.895121 0.511397 0.028 Uiso 1 1 calc R U . . .
C125 C 0.6516(3) 0.9987(6) 0.4470(3) 0.0254(13) Uani 1 1 d . . . . .
H125 H 0.623269 1.031498 0.477715 0.030 Uiso 1 1 calc R U . . .
C126 C 0.6336(3) 1.0322(6) 0.3815(3) 0.0213(12) Uani 1 1 d . . . . .
H126 H 0.593803 1.091369 0.368458 0.026 Uiso 1 1 calc R U . . .
N131 N 0.7221(2) 0.7520(5) 0.2608(2) 0.0182(9) Uani 1 1 d . . . . .
C132 C 0.7147(3) 0.7602(6) 0.1952(3) 0.0194(12) Uani 1 1 d . . . . .
N133 N 0.6540(2) 0.6826(5) 0.1710(2) 0.0183(10) Uani 1 1 d . . . . .
C134 C 0.6296(3) 0.6242(6) 0.2224(3) 0.0210(12) Uani 1 1 d . . . . .
H134 H 0.589833 0.563558 0.218866 0.025 Uiso 1 1 calc R U . . .
C135 C 0.6709(3) 0.6665(5) 0.2782(3) 0.0201(11) Uani 1 1 d . . . . .
H135 H 0.666050 0.642491 0.321251 0.024 Uiso 1 1 calc R U . . .
C141 C 0.5447(3) 0.6089(6) 0.0892(2) 0.0189(11) Uani 1 1 d . . . . .
C142 C 0.4764(3) 0.6772(6) 0.0806(3) 0.0221(12) Uani 1 1 d . . . . .
C143 C 0.4076(3) 0.6109(7) 0.0689(3) 0.0270(14) Uani 1 1 d . . . . .
H143 H 0.360973 0.656316 0.062776 0.032 Uiso 1 1 calc R U . . .
C144 C 0.4059(3) 0.4819(7) 0.0662(3) 0.0278(14) Uani 1 1 d . . . . .
H144 H 0.358468 0.438851 0.058348 0.033 Uiso 1 1 calc R U . . .
C145 C 0.4737(4) 0.4136(6) 0.0749(3) 0.0277(14) Uani 1 1 d . . . . .
H145 H 0.473046 0.324011 0.073157 0.033 Uiso 1 1 calc R U . . .
C146 C 0.5419(3) 0.4790(6) 0.0860(3) 0.0237(12) Uani 1 1 d . . . . .
H146 H 0.588326 0.432937 0.091554 0.028 Uiso 1 1 calc R U . . .
Se21 Se 0.40700(4) 0.07317(6) 0.38991(3) 0.02587(16) Uani 1 1 d . . . . .
Se22 Se 0.22471(3) 0.28116(6) 0.35886(3) 0.02350(16) Uani 1 1 d . . . . .
C21 C 0.3509(3) 0.1050(6) 0.2304(3) 0.0209(12) Uani 1 1 d . . . . .
H21A H 0.309689 0.109504 0.256453 0.025 Uiso 1 1 calc R U . . .
H21B H 0.365721 0.015418 0.227872 0.025 Uiso 1 1 calc R U . . .
C22 C 0.5296(3) 0.3106(6) 0.4085(3) 0.0215(12) Uani 1 1 d . . . . .
H22A H 0.583845 0.284939 0.417860 0.026 Uiso 1 1 calc R U . . .
H22B H 0.503514 0.268879 0.440897 0.026 Uiso 1 1 calc R U . . .
C23 C 0.3791(3) 0.4521(6) 0.4036(3) 0.0228(12) Uani 1 1 d . . . . .
H23A H 0.385309 0.365806 0.421981 0.027 Uiso 1 1 calc R U . . .
H23B H 0.344523 0.499026 0.427311 0.027 Uiso 1 1 calc R U . . .
C24 C 0.2230(3) 0.2998(6) 0.1992(3) 0.0221(12) Uani 1 1 d . . . . .
H24A H 0.179326 0.351899 0.178094 0.027 Uiso 1 1 calc R U . . .
H24B H 0.202775 0.231325 0.223561 0.027 Uiso 1 1 calc R U . . .
N211 N 0.4173(2) 0.1780(5) 0.2639(2) 0.0178(9) Uani 1 1 d . . . . .
C212 C 0.4392(3) 0.1785(6) 0.3299(3) 0.0217(12) Uani 1 1 d . . . . .
N213 N 0.4953(2) 0.2673(5) 0.3427(2) 0.0201(10) Uani 1 1 d . . . . .
C214 C 0.5126(3) 0.3121(6) 0.2845(3) 0.0211(12) Uani 1 1 d . . . . .
H214 H 0.551362 0.371216 0.280004 0.025 Uiso 1 1 calc R U . . .
C215 C 0.4645(3) 0.2563(6) 0.2357(3) 0.0245(13) Uani 1 1 d . . . . .
H215 H 0.463131 0.268317 0.190259 0.029 Uiso 1 1 calc R U . . .
C221 C 0.5246(3) 0.4518(6) 0.4163(3) 0.0186(11) Uani 1 1 d . . . . .
C222 C 0.4555(3) 0.5168(6) 0.4137(3) 0.0212(12) Uani 1 1 d . . . . .
C223 C 0.4570(4) 0.6478(6) 0.4212(3) 0.0258(13) Uani 1 1 d . . . . .
H223 H 0.410360 0.692314 0.418809 0.031 Uiso 1 1 calc R U . . .
C224 C 0.5250(4) 0.7146(6) 0.4319(3) 0.0291(14) Uani 1 1 d . . . . .
H224 H 0.524636 0.803796 0.436408 0.035 Uiso 1 1 calc R U . . .
C225 C 0.5930(4) 0.6512(7) 0.4361(3) 0.0311(14) Uani 1 1 d . . . . .
H225 H 0.639913 0.695778 0.444448 0.037 Uiso 1 1 calc R U . . .
C226 C 0.5921(3) 0.5197(7) 0.4277(3) 0.0267(13) Uani 1 1 d . . . . .
H226 H 0.639044 0.476103 0.429976 0.032 Uiso 1 1 calc R U . . .
N231 N 0.3447(3) 0.4448(5) 0.3341(2) 0.0199(10) Uani 1 1 d . . . . .
C232 C 0.2848(3) 0.3695(6) 0.3109(3) 0.0207(12) Uani 1 1 d . . . . .
N233 N 0.2745(2) 0.3777(5) 0.2447(2) 0.0188(10) Uani 1 1 d . . . . .
C234 C 0.3257(3) 0.4634(6) 0.2271(3) 0.0227(12) Uani 1 1 d . . . . .
H234 H 0.329290 0.488290 0.183910 0.027 Uiso 1 1 calc R U . . .
C235 C 0.3695(3) 0.5050(6) 0.2826(3) 0.0220(12) Uani 1 1 d . . . . .
H235 H 0.409845 0.564434 0.285896 0.026 Uiso 1 1 calc R U . . .
C241 C 0.2610(3) 0.2431(6) 0.1475(3) 0.0206(12) Uani 1 1 d . . . . .
C242 C 0.3208(3) 0.1539(5) 0.1615(3) 0.0188(11) Uani 1 1 d . . . . .
C243 C 0.3518(3) 0.1039(6) 0.1104(3) 0.0257(13) Uani 1 1 d . . . . .
H243 H 0.392215 0.044617 0.119562 0.031 Uiso 1 1 calc R U . . .
C244 C 0.3242(4) 0.1394(6) 0.0455(3) 0.0275(13) Uani 1 1 d . . . . .
H244 H 0.345884 0.103922 0.011109 0.033 Uiso 1 1 calc R U . . .
C245 C 0.2657(3) 0.2257(6) 0.0316(3) 0.0244(13) Uani 1 1 d . . . . .
H245 H 0.245965 0.249086 -0.012214 0.029 Uiso 1 1 calc R U . . .
C246 C 0.2365(3) 0.2774(6) 0.0827(3) 0.0221(12) Uani 1 1 d . . . . .
H246 H 0.197741 0.339565 0.073129 0.027 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se11 C112 1.850(6) . ?
Se12 C132 1.827(6) . ?
C11 N111 1.475(7) . ?
C11 C142 1.520(9) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N113 1.476(7) . ?
C12 C121 1.513(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N131 1.471(7) . ?
C13 C122 1.516(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N133 1.482(7) . ?
C14 C141 1.514(8) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N111 C112 1.349(8) . ?
N111 C115 1.385(8) . ?
C112 N113 1.357(7) . ?
N113 C114 1.388(8) . ?
C114 C115 1.346(8) . ?
C114 H114 0.9500 . ?
C115 H115 0.9500 . ?
C121 C126 1.384(8) . ?
C121 C122 1.416(8) . ?
C122 C123 1.388(8) . ?
C123 C124 1.379(8) . ?
C123 H123 0.9500 . ?
C124 C125 1.383(9) . ?
C124 H124 0.9500 . ?
C125 C126 1.389(8) . ?
C125 H125 0.9500 . ?
C126 H126 0.9500 . ?
N131 C132 1.352(7) . ?
N131 C135 1.380(8) . ?
C132 N133 1.381(7) . ?
N133 C134 1.372(7) . ?
C134 C135 1.337(8) . ?
C134 H134 0.9500 . ?
C135 H135 0.9500 . ?
C141 C146 1.379(9) . ?
C141 C142 1.400(8) . ?
C142 C143 1.397(8) . ?
C143 C144 1.368(10) . ?
C143 H143 0.9500 . ?
C144 C145 1.392(10) . ?
C144 H144 0.9500 . ?
C145 C146 1.384(9) . ?
C145 H145 0.9500 . ?
C146 H146 0.9500 . ?
Se21 C212 1.843(6) . ?
Se22 C232 1.847(6) . ?
C21 N211 1.480(7) . ?
C21 C242 1.528(8) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 N213 1.471(7) . ?
C22 C221 1.510(8) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 N231 1.468(7) . ?
C23 C222 1.506(8) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 N233 1.454(7) . ?
C24 C241 1.498(8) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
N211 C212 1.359(7) . ?
N211 C215 1.386(8) . ?
C212 N213 1.364(8) . ?
N213 C214 1.386(7) . ?
C214 C215 1.344(8) . ?
C214 H214 0.9500 . ?
C215 H215 0.9500 . ?
C221 C226 1.386(8) . ?
C221 C222 1.406(8) . ?
C222 C223 1.397(9) . ?
C223 C224 1.388(9) . ?
C223 H223 0.9500 . ?
C224 C225 1.376(10) . ?
C224 H224 0.9500 . ?
C225 C226 1.404(10) . ?
C225 H225 0.9500 . ?
C226 H226 0.9500 . ?
N231 C232 1.351(8) . ?
N231 C235 1.386(7) . ?
C232 N233 1.359(7) . ?
N233 C234 1.383(8) . ?
C234 C235 1.348(8) . ?
C234 H234 0.9500 . ?
C235 H235 0.9500 . ?
C241 C246 1.389(8) . ?
C241 C242 1.416(8) . ?
C242 C243 1.388(8) . ?
C243 C244 1.404(9) . ?
C243 H243 0.9500 . ?
C244 C245 1.379(9) . ?
C244 H244 0.9500 . ?
C245 C246 1.379(8) . ?
C245 H245 0.9500 . ?
C246 H246 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
N111 C11 C142 111.9(5) . . ?
N111 C11 H11A 109.2 . . ?
C142 C11 H11A 109.2 . . ?
N111 C11 H11B 109.2 . . ?
C142 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N113 C12 C121 113.1(5) . . ?
N113 C12 H12A 109.0 . . ?
C121 C12 H12A 109.0 . . ?
N113 C12 H12B 109.0 . . ?
C121 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
N131 C13 C122 110.7(4) . . ?
N131 C13 H13A 109.5 . . ?
C122 C13 H13A 109.5 . . ?
N131 C13 H13B 109.5 . . ?
C122 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
N133 C14 C141 111.3(4) . . ?
N133 C14 H14A 109.4 . . ?
C141 C14 H14A 109.4 . . ?
N133 C14 H14B 109.4 . . ?
C141 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C112 N111 C115 110.2(5) . . ?
C112 N111 C11 124.8(5) . . ?
C115 N111 C11 124.6(5) . . ?
N111 C112 N113 106.0(5) . . ?
N111 C112 Se11 126.4(4) . . ?
N113 C112 Se11 127.3(4) . . ?
C112 N113 C114 109.4(5) . . ?
C112 N113 C12 123.7(5) . . ?
C114 N113 C12 126.7(4) . . ?
C115 C114 N113 107.4(5) . . ?
C115 C114 H114 126.3 . . ?
N113 C114 H114 126.3 . . ?
C114 C115 N111 106.7(5) . . ?
C114 C115 H115 126.6 . . ?
N111 C115 H115 126.6 . . ?
C126 C121 C122 118.0(5) . . ?
C126 C121 C12 118.8(5) . . ?
C122 C121 C12 123.2(5) . . ?
C123 C122 C121 118.6(5) . . ?
C123 C122 C13 118.9(5) . . ?
C121 C122 C13 122.5(5) . . ?
C124 C123 C122 122.3(5) . . ?
C124 C123 H123 118.8 . . ?
C122 C123 H123 118.8 . . ?
C123 C124 C125 119.5(5) . . ?
C123 C124 H124 120.3 . . ?
C125 C124 H124 120.3 . . ?
C124 C125 C126 118.7(5) . . ?
C124 C125 H125 120.6 . . ?
C126 C125 H125 120.6 . . ?
C121 C126 C125 122.8(6) . . ?
C121 C126 H126 118.6 . . ?
C125 C126 H126 118.6 . . ?
C132 N131 C135 111.0(5) . . ?
C132 N131 C13 124.0(5) . . ?
C135 N131 C13 124.8(4) . . ?
N131 C132 N133 104.9(5) . . ?
N131 C132 Se12 127.8(4) . . ?
N133 C132 Se12 127.2(4) . . ?
C134 N133 C132 108.8(4) . . ?
C134 N133 C14 128.3(5) . . ?
C132 N133 C14 122.9(5) . . ?
C135 C134 N133 108.9(5) . . ?
C135 C134 H134 125.6 . . ?
N133 C134 H134 125.6 . . ?
C134 C135 N131 106.3(5) . . ?
C134 C135 H135 126.9 . . ?
N131 C135 H135 126.9 . . ?
C146 C141 C142 119.1(5) . . ?
C146 C141 C14 118.1(5) . . ?
C142 C141 C14 122.7(6) . . ?
C143 C142 C141 118.6(6) . . ?
C143 C142 C11 118.4(5) . . ?
C141 C142 C11 123.0(5) . . ?
C144 C143 C142 121.4(6) . . ?
C144 C143 H143 119.3 . . ?
C142 C143 H143 119.3 . . ?
C143 C144 C145 120.1(6) . . ?
C143 C144 H144 119.9 . . ?
C145 C144 H144 119.9 . . ?
C146 C145 C144 118.6(6) . . ?
C146 C145 H145 120.7 . . ?
C144 C145 H145 120.7 . . ?
C141 C146 C145 122.0(6) . . ?
C141 C146 H146 119.0 . . ?
C145 C146 H146 119.0 . . ?
N211 C21 C242 112.4(4) . . ?
N211 C21 H21A 109.1 . . ?
C242 C21 H21A 109.1 . . ?
N211 C21 H21B 109.1 . . ?
C242 C21 H21B 109.1 . . ?
H21A C21 H21B 107.9 . . ?
N213 C22 C221 112.7(5) . . ?
N213 C22 H22A 109.0 . . ?
C221 C22 H22A 109.0 . . ?
N213 C22 H22B 109.0 . . ?
C221 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
N231 C23 C222 111.7(5) . . ?
N231 C23 H23A 109.3 . . ?
C222 C23 H23A 109.3 . . ?
N231 C23 H23B 109.3 . . ?
C222 C23 H23B 109.3 . . ?
H23A C23 H23B 107.9 . . ?
N233 C24 C241 112.4(4) . . ?
N233 C24 H24A 109.1 . . ?
C241 C24 H24A 109.1 . . ?
N233 C24 H24B 109.1 . . ?
C241 C24 H24B 109.1 . . ?
H24A C24 H24B 107.9 . . ?
C212 N211 C215 109.8(5) . . ?
C212 N211 C21 122.6(4) . . ?
C215 N211 C21 127.6(4) . . ?
N211 C212 N213 105.6(5) . . ?
N211 C212 Se21 127.9(4) . . ?
N213 C212 Se21 126.3(4) . . ?
C212 N213 C214 109.7(4) . . ?
C212 N213 C22 124.5(5) . . ?
C214 N213 C22 125.9(5) . . ?
C215 C214 N213 107.3(5) . . ?
C215 C214 H214 126.4 . . ?
N213 C214 H214 126.4 . . ?
C214 C215 N211 107.3(5) . . ?
C214 C215 H215 126.3 . . ?
N211 C215 H215 126.3 . . ?
C226 C221 C222 118.8(6) . . ?
C226 C221 C22 117.8(5) . . ?
C222 C221 C22 123.4(5) . . ?
C223 C222 C221 118.9(5) . . ?
C223 C222 C23 117.9(5) . . ?
C221 C222 C23 123.3(6) . . ?
C224 C223 C222 121.6(6) . . ?
C224 C223 H223 119.2 . . ?
C222 C223 H223 119.2 . . ?
C225 C224 C223 119.8(6) . . ?
C225 C224 H224 120.1 . . ?
C223 C224 H224 120.1 . . ?
C224 C225 C226 119.2(6) . . ?
C224 C225 H225 120.4 . . ?
C226 C225 H225 120.4 . . ?
C221 C226 C225 121.7(6) . . ?
C221 C226 H226 119.1 . . ?
C225 C226 H226 119.1 . . ?
C232 N231 C235 109.7(5) . . ?
C232 N231 C23 123.2(5) . . ?
C235 N231 C23 127.0(5) . . ?
N231 C232 N233 106.2(5) . . ?
N231 C232 Se22 127.2(4) . . ?
N233 C232 Se22 126.5(4) . . ?
C232 N233 C234 109.6(5) . . ?
C232 N233 C24 125.4(5) . . ?
C234 N233 C24 124.8(5) . . ?
C235 C234 N233 107.2(5) . . ?
C235 C234 H234 126.4 . . ?
N233 C234 H234 126.4 . . ?
C234 C235 N231 107.2(5) . . ?
C234 C235 H235 126.4 . . ?
N231 C235 H235 126.4 . . ?
C246 C241 C242 118.0(5) . . ?
C246 C241 C24 119.2(5) . . ?
C242 C241 C24 122.8(5) . . ?
C243 C242 C241 119.0(5) . . ?
C243 C242 C21 117.9(5) . . ?
C241 C242 C21 123.0(5) . . ?
C242 C243 C244 121.1(6) . . ?
C242 C243 H243 119.4 . . ?
C244 C243 H243 119.4 . . ?
C245 C244 C243 120.0(5) . . ?
C245 C244 H244 120.0 . . ?
C243 C244 H244 120.0 . . ?
C246 C245 C244 118.6(5) . . ?
C246 C245 H245 120.7 . . ?
C244 C245 H245 120.7 . . ?
C245 C246 C241 123.2(5) . . ?
C245 C246 H246 118.4 . . ?
C241 C246 H246 118.4 . . ?

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
C142 C11 N111 C112 125.9(6) . . . . ?
C142 C11 N111 C115 -46.4(7) . . . . ?
C115 N111 C112 N113 4.1(6) . . . . ?
C11 N111 C112 N113 -169.1(5) . . . . ?
C115 N111 C112 Se11 -169.5(4) . . . . ?
C11 N111 C112 Se11 17.3(8) . . . . ?
N111 C112 N113 C114 -4.3(6) . . . . ?
Se11 C112 N113 C114 169.3(4) . . . . ?
N111 C112 N113 C12 171.4(5) . . . . ?
Se11 C112 N113 C12 -15.0(8) . . . . ?
C121 C12 N113 C112 -163.5(5) . . . . ?
C121 C12 N113 C114 11.4(8) . . . . ?
C112 N113 C114 C115 2.9(6) . . . . ?
C12 N113 C114 C115 -172.7(5) . . . . ?
N113 C114 C115 N111 -0.3(6) . . . . ?
C112 N111 C115 C114 -2.4(7) . . . . ?
C11 N111 C115 C114 170.9(5) . . . . ?
N113 C12 C121 C126 -83.0(7) . . . . ?
N113 C12 C121 C122 97.6(6) . . . . ?
C126 C121 C122 C123 -1.8(8) . . . . ?
C12 C121 C122 C123 177.5(5) . . . . ?
C126 C121 C122 C13 177.6(5) . . . . ?
C12 C121 C122 C13 -3.1(8) . . . . ?
N131 C13 C122 C123 116.2(6) . . . . ?
N131 C13 C122 C121 -63.2(7) . . . . ?
C121 C122 C123 C124 1.9(9) . . . . ?
C13 C122 C123 C124 -177.5(5) . . . . ?
C122 C123 C124 C125 0.4(9) . . . . ?
C123 C124 C125 C126 -2.7(9) . . . . ?
C122 C121 C126 C125 -0.4(9) . . . . ?
C12 C121 C126 C125 -179.8(5) . . . . ?
C124 C125 C126 C121 2.7(9) . . . . ?
C122 C13 N131 C132 126.9(5) . . . . ?
C122 C13 N131 C135 -47.8(7) . . . . ?
C135 N131 C132 N133 3.5(6) . . . . ?
C13 N131 C132 N133 -171.9(5) . . . . ?
C135 N131 C132 Se12 -174.0(4) . . . . ?
C13 N131 C132 Se12 10.7(8) . . . . ?
N131 C132 N133 C134 -3.7(6) . . . . ?
Se12 C132 N133 C134 173.8(4) . . . . ?
N131 C132 N133 C14 174.8(5) . . . . ?
Se12 C132 N133 C14 -7.7(8) . . . . ?
C141 C14 N133 C134 13.2(8) . . . . ?
C141 C14 N133 C132 -165.0(5) . . . . ?
C132 N133 C134 C135 2.6(6) . . . . ?
C14 N133 C134 C135 -175.8(5) . . . . ?
N133 C134 C135 N131 -0.4(6) . . . . ?
C132 N131 C135 C134 -2.0(6) . . . . ?
C13 N131 C135 C134 173.3(5) . . . . ?
N133 C14 C141 C146 -87.1(6) . . . . ?
N133 C14 C141 C142 94.5(6) . . . . ?
C146 C141 C142 C143 0.0(7) . . . . ?
C14 C141 C142 C143 178.4(5) . . . . ?
C146 C141 C142 C11 -180.0(5) . . . . ?
C14 C141 C142 C11 -1.6(8) . . . . ?
N111 C11 C142 C143 113.6(6) . . . . ?
N111 C11 C142 C141 -66.4(7) . . . . ?
C141 C142 C143 C144 0.3(8) . . . . ?
C11 C142 C143 C144 -179.7(5) . . . . ?
C142 C143 C144 C145 -0.2(8) . . . . ?
C143 C144 C145 C146 -0.2(8) . . . . ?
C142 C141 C146 C145 -0.4(8) . . . . ?
C14 C141 C146 C145 -178.9(5) . . . . ?
C144 C145 C146 C141 0.5(8) . . . . ?
C242 C21 N211 C212 159.7(5) . . . . ?
C242 C21 N211 C215 -18.6(8) . . . . ?
C215 N211 C212 N213 6.0(6) . . . . ?
C21 N211 C212 N213 -172.5(5) . . . . ?
C215 N211 C212 Se21 -169.2(4) . . . . ?
C21 N211 C212 Se21 12.3(8) . . . . ?
N211 C212 N213 C214 -5.8(6) . . . . ?
Se21 C212 N213 C214 169.6(4) . . . . ?
N211 C212 N213 C22 172.5(5) . . . . ?
Se21 C212 N213 C22 -12.2(8) . . . . ?
C221 C22 N213 C212 -124.5(6) . . . . ?
C221 C22 N213 C214 53.4(7) . . . . ?
C212 N213 C214 C215 3.4(7) . . . . ?
C22 N213 C214 C215 -174.8(5) . . . . ?
N213 C214 C215 N211 0.4(6) . . . . ?
C212 N211 C215 C214 -4.1(7) . . . . ?
C21 N211 C215 C214 174.3(5) . . . . ?
N213 C22 C221 C226 -115.1(5) . . . . ?
N213 C22 C221 C222 66.2(7) . . . . ?
C226 C221 C222 C223 1.6(8) . . . . ?
C22 C221 C222 C223 -179.7(5) . . . . ?
C226 C221 C222 C23 -178.1(5) . . . . ?
C22 C221 C222 C23 0.6(8) . . . . ?
N231 C23 C222 C223 89.0(6) . . . . ?
N231 C23 C222 C221 -91.3(7) . . . . ?
C221 C222 C223 C224 -0.9(8) . . . . ?
C23 C222 C223 C224 178.7(5) . . . . ?
C222 C223 C224 C225 -0.6(8) . . . . ?
C223 C224 C225 C226 1.5(9) . . . . ?
C222 C221 C226 C225 -0.7(8) . . . . ?
C22 C221 C226 C225 -179.5(5) . . . . ?
C224 C225 C226 C221 -0.9(9) . . . . ?
C222 C23 N231 C232 165.8(5) . . . . ?
C222 C23 N231 C235 -10.1(8) . . . . ?
C235 N231 C232 N233 3.0(6) . . . . ?
C23 N231 C232 N233 -173.5(5) . . . . ?
C235 N231 C232 Se22 -173.4(4) . . . . ?
C23 N231 C232 Se22 10.1(8) . . . . ?
N231 C232 N233 C234 -3.1(6) . . . . ?
Se22 C232 N233 C234 173.3(4) . . . . ?
N231 C232 N233 C24 171.4(5) . . . . ?
Se22 C232 N233 C24 -12.2(8) . . . . ?
C241 C24 N233 C232 -130.1(6) . . . . ?
C241 C24 N233 C234 43.6(7) . . . . ?
C232 N233 C234 C235 2.1(7) . . . . ?
C24 N233 C234 C235 -172.5(5) . . . . ?
N233 C234 C235 N231 -0.3(6) . . . . ?
C232 N231 C235 C234 -1.7(6) . . . . ?
C23 N231 C235 C234 174.6(5) . . . . ?
N233 C24 C241 C246 -115.7(6) . . . . ?
N233 C24 C241 C242 65.1(7) . . . . ?
C246 C241 C242 C243 -0.7(8) . . . . ?
C24 C241 C242 C243 178.5(5) . . . . ?
C246 C241 C242 C21 -177.8(5) . . . . ?
C24 C241 C242 C21 1.5(8) . . . . ?
N211 C21 C242 C243 89.1(6) . . . . ?
N211 C21 C242 C241 -93.8(6) . . . . ?
C241 C242 C243 C244 -0.6(9) . . . . ?
C21 C242 C243 C244 176.6(5) . . . . ?
C242 C243 C244 C245 0.3(9) . . . . ?
C243 C244 C245 C246 1.3(9) . . . . ?
C244 C245 C246 C241 -2.7(9) . . . . ?
C242 C241 C246 C245 2.4(9) . . . . ?
C24 C241 C246 C245 -176.9(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C11 H11A Se11 0.99 2.82 3.326(6) 112.2 . yes
C12 H12B Se12 0.99 3.18 4.058(6) 149.2 . yes
C13 H13A Se12 0.99 2.80 3.311(6) 112.8 . yes
C13 H13B Se11 0.99 2.98 3.944(6) 163.5 2_645 yes
C115 H115 Se22 0.95 3.15 3.781(6) 125.7 2 yes
C22 H22A Se12 0.99 3.16 3.907(6) 133.3 2_645 yes
C22 H22B Se21 0.99 2.78 3.312(6) 114.1 . yes
C24 H24A Se21 0.99 3.02 3.957(6) 159.4 2 yes
C24 H24B Se22 0.99 2.82 3.324(6) 112.1 . yes

_refine_diff_density_max         1.506
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.135



####################################################################### 
# 
# 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_ah60c_180425
_database_code_depnum_ccdc_archive 'CCDC 2247959'
loop_
_audit_author_name
_audit_author_address
'Alexandre N. Sobolev'
;Centre for Microscopy Characterisation and Analysis The University of Western Australia
Australia
;
_audit_update_record             
;
2023-03-11 deposited with the CCDC.	2023-05-18 downloaded from the CCDC.
;

#==============================================================================

# 6. CRYSTALLOGRAPHY

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_weight         498.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   12.3930(8)
_cell_length_b                   18.8028(13)
_cell_length_c                   8.6492(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2015.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2354
_cell_measurement_theta_min      6.221
_cell_measurement_theta_max      66.157
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0218759653
_diffrn_orient_matrix_UB_12      -0.0806960242
_diffrn_orient_matrix_UB_13      -0.0023331614
_diffrn_orient_matrix_UB_21      0.1206358550
_diffrn_orient_matrix_UB_22      -0.0139300046
_diffrn_orient_matrix_UB_23      -0.0303434422
_diffrn_orient_matrix_UB_31      0.0205907793
_diffrn_orient_matrix_UB_32      -0.0035658641
_diffrn_orient_matrix_UB_33      0.1754053942
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.024
_exptl_absorpt_coefficient_mu    4.700
_shelx_estimated_absorpt_T_min   0.358
_shelx_estimated_absorpt_T_max   0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.69526
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_detector_area_resol_mean 10.4738
_diffrn_reflns_number            17634
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_av_R_equivalents  0.1109
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.630
_diffrn_reflns_theta_max         67.135
_diffrn_reflns_theta_full        67.135
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1856
_reflns_number_gt                1149
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2015/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'X-Seed v. 4.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1250P)²+3.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1856
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0721
_refine_ls_wR_factor_ref         0.2157
_refine_ls_wR_factor_gt          0.1832
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.90184(7) 0.57167(4) 0.48886(9) 0.0495(4) Uani 1 1 d . . . . .
C1 C 0.7527(6) 0.5780(4) 0.5153(8) 0.0447(17) Uani 1 1 d . . . . .
N2 N 0.6784(5) 0.5775(3) 0.4031(7) 0.0505(17) Uani 1 1 d . . . . .
C3 C 0.5783(6) 0.5756(4) 0.4762(9) 0.0485(19) Uani 1 1 d . . . . .
H3 H 0.510588 0.574767 0.424643 0.058 Uiso 1 1 calc R U . . .
C4 C 0.5909(7) 0.5752(4) 0.6233(11) 0.057(2) Uani 1 1 d . . . . .
H4 H 0.535127 0.573710 0.698501 0.068 Uiso 1 1 calc R U . . .
N5 N 0.7002(6) 0.5772(3) 0.6525(7) 0.0495(15) Uani 1 1 d . . . . .
C2 C 0.6977(8) 0.5946(4) 0.2438(9) 0.054(2) Uani 1 1 d . . . . .
H2A H 0.641077 0.572897 0.178348 0.064 Uiso 1 1 calc R U . . .
H2B H 0.768418 0.575329 0.211233 0.064 Uiso 1 1 calc R U . . .
C21 C 0.6967(7) 0.6752(4) 0.2234(8) 0.0483(19) Uani 1 1 d . . . . .
C22 C 0.7918(8) 0.7117(5) 0.2152(8) 0.059(2) Uani 1 1 d . . . . .
H22 H 0.858131 0.686500 0.209549 0.071 Uiso 1 1 calc R U . . .
C23 C 0.6002(8) 0.7133(5) 0.2268(10) 0.063(2) Uani 1 1 d . . . . .
H23 H 0.533559 0.688418 0.229065 0.076 Uiso 1 1 calc R U . . .
C5 C 0.7479(7) 0.5958(4) 0.8007(9) 0.0503(19) Uani 1 1 d . . . . .
H5A H 0.822020 0.576380 0.807309 0.060 Uiso 1 1 calc R U . . .
H5B H 0.704664 0.575032 0.885654 0.060 Uiso 1 1 calc R U . . .
C51 C 0.7508(7) 0.6751(4) 0.8160(8) 0.049(2) Uani 1 1 d . . . . .
C52 C 0.8453(7) 0.7135(4) 0.7939(8) 0.055(2) Uani 1 1 d . . . . .
H52 H 0.911207 0.688735 0.778481 0.066 Uiso 1 1 calc R U . . .
C53 C 0.6573(7) 0.7129(5) 0.8461(8) 0.054(2) Uani 1 1 d . . . . .
H53 H 0.592270 0.687927 0.866969 0.065 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C1 1.867(8) . ?
C1 N2 1.337(10) . ?
C1 N5 1.353(9) . ?
N2 C3 1.393(10) . ?
N2 C2 1.435(11) . ?
C3 C4 1.282(11) . ?
C3 H3 0.9500 . ?
C4 N5 1.378(10) . ?
C4 H4 0.9500 . ?
N5 C5 1.454(10) . ?
C2 C21 1.525(11) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C21 C22 1.366(13) . ?
C21 C23 1.394(13) . ?
C22 C22 1.440(19) 7_575 ?
C22 H22 0.9500 . ?
C23 C23 1.379(18) 7_575 ?
C23 H23 0.9500 . ?
C5 C51 1.498(11) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C51 C53 1.383(12) . ?
C51 C52 1.388(12) . ?
C52 C52 1.373(17) 7_575 ?
C52 H52 0.9500 . ?
C53 C53 1.397(17) 7_575 ?
C53 H53 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N5 107.8(7) . . ?
N2 C1 Se1 126.3(6) . . ?
N5 C1 Se1 125.6(6) . . ?
C1 N2 C3 106.5(6) . . ?
C1 N2 C2 125.5(7) . . ?
C3 N2 C2 126.1(7) . . ?
C4 C3 N2 110.0(7) . . ?
C4 C3 H3 125.0 . . ?
N2 C3 H3 125.0 . . ?
C3 C4 N5 107.6(8) . . ?
C3 C4 H4 126.2 . . ?
N5 C4 H4 126.2 . . ?
C1 N5 C4 108.1(7) . . ?
C1 N5 C5 125.1(7) . . ?
C4 N5 C5 124.6(7) . . ?
N2 C2 C21 109.5(6) . . ?
N2 C2 H2A 109.8 . . ?
C21 C2 H2A 109.8 . . ?
N2 C2 H2B 109.8 . . ?
C21 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
C22 C21 C23 118.9(8) . . ?
C22 C21 C2 119.9(9) . . ?
C23 C21 C2 121.0(8) . . ?
C21 C22 C22 120.2(5) . 7_575 ?
C21 C22 H22 119.9 . . ?
C22 C22 H22 119.9 7_575 . ?
C23 C23 C21 120.9(5) 7_575 . ?
C23 C23 H23 119.5 7_575 . ?
C21 C23 H23 119.5 . . ?
N5 C5 C51 109.1(7) . . ?
N5 C5 H5A 109.9 . . ?
C51 C5 H5A 109.9 . . ?
N5 C5 H5B 109.9 . . ?
C51 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
C53 C51 C52 117.7(8) . . ?
C53 C51 C5 120.5(8) . . ?
C52 C51 C5 121.7(8) . . ?
C52 C52 C51 121.3(5) 7_575 . ?
C52 C52 H52 119.3 7_575 . ?
C51 C52 H52 119.3 . . ?
C51 C53 C53 120.9(5) . 7_575 ?
C51 C53 H53 119.6 . . ?
C53 C53 H53 119.6 7_575 . ?

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
N5 C1 N2 C3 -0.5(7) . . . . ?
Se1 C1 N2 C3 173.8(5) . . . . ?
N5 C1 N2 C2 164.4(7) . . . . ?
Se1 C1 N2 C2 -21.3(10) . . . . ?
C1 N2 C3 C4 0.1(9) . . . . ?
C2 N2 C3 C4 -164.8(7) . . . . ?
N2 C3 C4 N5 0.4(10) . . . . ?
N2 C1 N5 C4 0.8(8) . . . . ?
Se1 C1 N5 C4 -173.6(6) . . . . ?
N2 C1 N5 C5 -163.1(7) . . . . ?
Se1 C1 N5 C5 22.6(10) . . . . ?
C3 C4 N5 C1 -0.7(9) . . . . ?
C3 C4 N5 C5 163.3(7) . . . . ?
C1 N2 C2 C21 -81.6(10) . . . . ?
C3 N2 C2 C21 80.5(10) . . . . ?
N2 C2 C21 C22 99.9(9) . . . . ?
N2 C2 C21 C23 -74.3(10) . . . . ?
C23 C21 C22 C22 2.0(9) . . . 7_575 ?
C2 C21 C22 C22 -172.3(5) . . . 7_575 ?
C22 C21 C23 C23 -2.0(9) . . . 7_575 ?
C2 C21 C23 C23 172.2(5) . . . 7_575 ?
C1 N5 C5 C51 80.1(10) . . . . ?
C4 N5 C5 C51 -81.2(10) . . . . ?
N5 C5 C51 C53 74.5(9) . . . . ?
N5 C5 C51 C52 -102.5(9) . . . . ?
C53 C51 C52 C52 -3.3(8) . . . 7_575 ?
C5 C51 C52 C52 173.8(5) . . . 7_575 ?
C52 C51 C53 C53 3.2(8) . . . 7_575 ?
C5 C51 C53 C53 -173.9(5) . . . 7_575 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H4 Se1 0.95 3.17 4.093(9) 164.6 6_557 yes

_refine_diff_density_max         1.496
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.190



