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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2280515'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;Universty Rennes
France
;
_audit_update_record             
;
2023-08-29 deposited with the CCDC.	2023-08-30 downloaded from the CCDC.
;

_audit_creation_date             2022-02-18T13:30:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C12 H12 N2 Se2'
_chemical_formula_moiety         'C12 H12 N2 Se2'
_chemical_formula_weight         342.16

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.0460(12)
_cell_length_b                   8.3234(5)
_cell_length_c                   18.3738(12)
_cell_angle_alpha                90
_cell_angle_beta                 118.457(3)
_cell_angle_gamma                90
_cell_volume                     2426.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5093
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.36
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.873
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    6.068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.422
_exptl_absorpt_correction_T_max  0.545

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.3571  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
# Ratio of Min/Max transmission:               0.4789                          #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 CCD-LDI-APEX2
_diffrn_detector_area_resol_mean 8.33
_diffrn_orient_matrix_ub_11      -0.053946
_diffrn_orient_matrix_ub_12      0.024999
_diffrn_orient_matrix_ub_13      -0.051015
_diffrn_orient_matrix_ub_21      0.032507
_diffrn_orient_matrix_ub_22      0.033109
_diffrn_orient_matrix_ub_23      -0.028937
_diffrn_orient_matrix_ub_31      -0.002415
_diffrn_orient_matrix_ub_32      -0.112753
_diffrn_orient_matrix_ub_33      -0.019808
_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_number            16796
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.522
_diffrn_reflns_theta_max         27.453
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_reflns_Friedel_coverage         0
_reflns_number_total             5489
_reflns_number_gt                3820
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0257P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5489
_refine_ls_number_parameters     297
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0669
_refine_ls_wR_factor_gt          0.0609
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      0.977
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.121

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
C1 C 0.2344(2) 0.1888(4) 0.43885(19) 0.0175(8) Uani 1 1 d . . . . .
C2 C 0.1686(2) 0.2163(4) 0.45669(19) 0.0164(8) Uani 1 1 d . . . . .
C3 C 0.1729(2) 0.1575(4) 0.53047(18) 0.0153(7) Uani 1 1 d . . . . .
C4 C 0.2451(2) 0.0718(4) 0.58538(19) 0.0162(8) Uani 1 1 d . . . . .
C5 C 0.3123(2) 0.0501(4) 0.56861(19) 0.0162(8) Uani 1 1 d . . . . .
C6 C 0.3079(2) 0.1074(4) 0.4941(2) 0.0166(8) Uani 1 1 d . . . . .
C7 C 0.1401(2) 0.1441(4) 0.2653(2) 0.0198(8) Uani 1 1 d . . . . .
C8 C -0.0048(2) 0.1837(4) 0.3467(2) 0.0220(8) Uani 1 1 d . . . . .
C9 C 0.1014(2) 0.1828(4) 0.5502(2) 0.0233(8) Uani 1 1 d . . . . .
H9A H 0.066 0.2719 0.5169 0.035 Uiso 1 1 calc R U . . .
H9B H 0.1244 0.2082 0.6091 0.035 Uiso 1 1 calc R U . . .
H9C H 0.0674 0.0846 0.5373 0.035 Uiso 1 1 calc R U . . .
C10 C 0.2520(2) 0.0011(4) 0.66437(19) 0.0228(8) Uani 1 1 d . . . . .
H10A H 0.2696 -0.1115 0.6692 0.034 Uiso 1 1 calc R U . . .
H10B H 0.1971 0.0073 0.663 0.034 Uiso 1 1 calc R U . . .
H10C H 0.2937 0.0617 0.712 0.034 Uiso 1 1 calc R U . . .
C11 C 0.3909(2) -0.0367(4) 0.6298(2) 0.0260(9) Uani 1 1 d . . . . .
H11A H 0.3976 -0.0243 0.6857 0.039 Uiso 1 1 calc R U . . .
H11B H 0.44 0.0089 0.628 0.039 Uiso 1 1 calc R U . . .
H11C H 0.386 -0.1511 0.6155 0.039 Uiso 1 1 calc R U . . .
C12 C 0.3801(2) 0.0752(4) 0.4758(2) 0.0284(9) Uani 1 1 d . . . . .
H12A H 0.3667 0.1206 0.4217 0.043 Uiso 1 1 calc R U . . .
H12B H 0.3886 -0.0409 0.4753 0.043 Uiso 1 1 calc R U . . .
H12C H 0.4316 0.1252 0.5187 0.043 Uiso 1 1 calc R U . . .
C13 C 0.3341(2) 0.5296(4) 0.55903(19) 0.0160(8) Uani 1 1 d . . . . .
C14 C 0.2737(2) 0.5426(4) 0.58581(19) 0.0158(8) Uani 1 1 d . . . . .
C15 C 0.1975(2) 0.6226(4) 0.5386(2) 0.0172(8) Uani 1 1 d . . . . .
C16 C 0.1827(2) 0.6907(4) 0.4622(2) 0.0183(8) Uani 1 1 d . . . . .
C17 C 0.2433(2) 0.6755(4) 0.43533(19) 0.0173(8) Uani 1 1 d . . . . .
C18 C 0.3193(2) 0.5937(4) 0.48285(19) 0.0151(7) Uani 1 1 d . . . . .
C19 C 0.5096(2) 0.5854(4) 0.6443(2) 0.0242(9) Uani 1 1 d . . . . .
C20 C 0.3602(2) 0.5848(4) 0.7588(2) 0.0225(8) Uani 1 1 d . . . . .
C21 C 0.1309(2) 0.6403(4) 0.5659(2) 0.0303(9) Uani 1 1 d . . . . .
H21A H 0.1527 0.5985 0.6223 0.045 Uiso 1 1 calc R U . . .
H21B H 0.0805 0.5797 0.5283 0.045 Uiso 1 1 calc R U . . .
H21C H 0.1164 0.754 0.5648 0.045 Uiso 1 1 calc R U . . .
C22 C 0.1009(2) 0.7776(4) 0.4093(2) 0.0316(10) Uani 1 1 d . . . . .
H22A H 0.1094 0.8935 0.419 0.047 Uiso 1 1 calc R U . . .
H22B H 0.058 0.7409 0.4238 0.047 Uiso 1 1 calc R U . . .
H22C H 0.0822 0.7548 0.3508 0.047 Uiso 1 1 calc R U . . .
C23 C 0.2267(2) 0.7507(4) 0.3544(2) 0.0279(9) Uani 1 1 d . . . . .
H23A H 0.2805 0.7746 0.3556 0.042 Uiso 1 1 calc R U . . .
H23B H 0.1947 0.8504 0.3459 0.042 Uiso 1 1 calc R U . . .
H23C H 0.1942 0.676 0.3089 0.042 Uiso 1 1 calc R U . . .
C24 C 0.3824(2) 0.5748(4) 0.4517(2) 0.0268(9) Uani 1 1 d . . . . .
H24A H 0.4208 0.6671 0.4694 0.04 Uiso 1 1 calc R U . . .
H24B H 0.3527 0.5691 0.3911 0.04 Uiso 1 1 calc R U . . .
H24C H 0.4148 0.4759 0.4742 0.04 Uiso 1 1 calc R U . . .
N1 N 0.0869(2) 0.0627(4) 0.22026(17) 0.0286(8) Uani 1 1 d . . . . .
N2 N -0.0546(2) 0.0848(4) 0.32449(19) 0.0335(8) Uani 1 1 d . . . . .
N3 N 0.5564(2) 0.6879(4) 0.65660(19) 0.0367(9) Uani 1 1 d . . . . .
N4 N 0.4022(2) 0.6817(4) 0.80363(19) 0.0369(9) Uani 1 1 d . . . . .
Se1 Se 0.22796(3) 0.27276(5) 0.33686(2) 0.02757(11) Uani 1 1 d . . . . .
Se2 Se 0.07345(2) 0.34803(4) 0.38220(2) 0.02180(10) Uani 1 1 d . . . . .
Se3 Se 0.43770(2) 0.41485(4) 0.62785(2) 0.02502(10) Uani 1 1 d . . . . .
Se4 Se 0.29285(2) 0.42956(4) 0.68586(2) 0.02636(11) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.394(5) . ?
C1 C6 1.403(5) . ?
C1 Se1 1.951(3) . ?
C2 C3 1.408(4) . ?
C2 Se2 1.945(3) . ?
C3 C4 1.403(4) . ?
C3 C9 1.513(4) . ?
C4 C5 1.399(5) . ?
C4 C10 1.515(4) . ?
C5 C6 1.417(4) . ?
C5 C11 1.509(4) . ?
C6 C12 1.515(5) . ?
C7 N1 1.144(4) . ?
C7 Se1 1.845(4) . ?
C8 N2 1.142(4) . ?
C8 Se2 1.847(4) . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 C14 1.398(4) . ?
C13 C18 1.399(4) . ?
C13 Se3 1.937(3) . ?
C14 C15 1.397(4) . ?
C14 Se4 1.944(3) . ?
C15 C16 1.418(4) . ?
C15 C21 1.513(5) . ?
C16 C17 1.402(5) . ?
C16 C22 1.510(5) . ?
C17 C18 1.402(4) . ?
C17 C23 1.507(4) . ?
C18 C24 1.508(4) . ?
C19 N3 1.145(4) . ?
C19 Se3 1.848(4) . ?
C20 N4 1.144(4) . ?
C20 Se4 1.842(4) . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?
C24 H24A 0.98 . ?
C24 H24B 0.98 . ?
C24 H24C 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.9(3) . . ?
C2 C1 Se1 120.0(2) . . ?
C6 C1 Se1 118.1(3) . . ?
C1 C2 C3 120.4(3) . . ?
C1 C2 Se2 119.5(2) . . ?
C3 C2 Se2 120.0(3) . . ?
C4 C3 C2 118.4(3) . . ?
C4 C3 C9 120.3(3) . . ?
C2 C3 C9 121.3(3) . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 C10 118.4(3) . . ?
C3 C4 C10 120.7(3) . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 C11 120.2(3) . . ?
C6 C5 C11 118.8(3) . . ?
C1 C6 C5 117.4(3) . . ?
C1 C6 C12 122.8(3) . . ?
C5 C6 C12 119.8(3) . . ?
N1 C7 Se1 178.4(3) . . ?
N2 C8 Se2 178.3(3) . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 120.9(3) . . ?
C14 C13 Se3 118.7(2) . . ?
C18 C13 Se3 120.4(3) . . ?
C15 C14 C13 121.4(3) . . ?
C15 C14 Se4 119.8(3) . . ?
C13 C14 Se4 118.6(2) . . ?
C14 C15 C16 118.0(3) . . ?
C14 C15 C21 122.9(3) . . ?
C16 C15 C21 119.0(3) . . ?
C17 C16 C15 120.1(3) . . ?
C17 C16 C22 120.3(3) . . ?
C15 C16 C22 119.6(3) . . ?
C18 C17 C16 121.3(3) . . ?
C18 C17 C23 119.4(3) . . ?
C16 C17 C23 119.2(3) . . ?
C13 C18 C17 118.2(3) . . ?
C13 C18 C24 121.4(3) . . ?
C17 C18 C24 120.4(3) . . ?
N3 C19 Se3 177.6(3) . . ?
N4 C20 Se4 179.4(3) . . ?
C15 C21 H21A 109.5 . . ?
C15 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C15 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C17 C23 H23A 109.5 . . ?
C17 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C17 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C18 C24 H24A 109.5 . . ?
C18 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C18 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C7 Se1 C1 96.57(14) . . ?
C8 Se2 C2 95.78(14) . . ?
C19 Se3 C13 96.40(14) . . ?
C20 Se4 C14 96.15(13) . . ?

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
C6 C1 C2 C3 -2.2(5) . . . . ?
Se1 C1 C2 C3 -179.4(2) . . . . ?
C6 C1 C2 Se2 174.0(2) . . . . ?
Se1 C1 C2 Se2 -3.2(4) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
Se2 C2 C3 C4 -175.8(2) . . . . ?
C1 C2 C3 C9 -178.6(3) . . . . ?
Se2 C2 C3 C9 5.1(4) . . . . ?
C2 C3 C4 C5 2.1(4) . . . . ?
C9 C3 C4 C5 -178.8(3) . . . . ?
C2 C3 C4 C10 -178.0(3) . . . . ?
C9 C3 C4 C10 1.0(4) . . . . ?
C3 C4 C5 C6 -2.9(5) . . . . ?
C10 C4 C5 C6 177.2(3) . . . . ?
C3 C4 C5 C11 177.6(3) . . . . ?
C10 C4 C5 C11 -2.2(4) . . . . ?
C2 C1 C6 C5 1.5(5) . . . . ?
Se1 C1 C6 C5 178.7(2) . . . . ?
C2 C1 C6 C12 179.7(3) . . . . ?
Se1 C1 C6 C12 -3.1(4) . . . . ?
C4 C5 C6 C1 1.1(4) . . . . ?
C11 C5 C6 C1 -179.4(3) . . . . ?
C4 C5 C6 C12 -177.2(3) . . . . ?
C11 C5 C6 C12 2.3(4) . . . . ?
C18 C13 C14 C15 -1.5(5) . . . . ?
Se3 C13 C14 C15 -179.4(2) . . . . ?
C18 C13 C14 Se4 172.9(2) . . . . ?
Se3 C13 C14 Se4 -5.1(3) . . . . ?
C13 C14 C15 C16 0.1(5) . . . . ?
Se4 C14 C15 C16 -174.2(2) . . . . ?
C13 C14 C15 C21 -179.5(3) . . . . ?
Se4 C14 C15 C21 6.2(4) . . . . ?
C14 C15 C16 C17 0.7(5) . . . . ?
C21 C15 C16 C17 -179.7(3) . . . . ?
C14 C15 C16 C22 179.7(3) . . . . ?
C21 C15 C16 C22 -0.6(5) . . . . ?
C15 C16 C17 C18 -0.2(5) . . . . ?
C22 C16 C17 C18 -179.2(3) . . . . ?
C15 C16 C17 C23 -179.2(3) . . . . ?
C22 C16 C17 C23 1.7(5) . . . . ?
C14 C13 C18 C17 1.9(5) . . . . ?
Se3 C13 C18 C17 179.9(2) . . . . ?
C14 C13 C18 C24 -177.5(3) . . . . ?
Se3 C13 C18 C24 0.5(4) . . . . ?
C16 C17 C18 C13 -1.1(5) . . . . ?
C23 C17 C18 C13 177.9(3) . . . . ?
C16 C17 C18 C24 178.3(3) . . . . ?
C23 C17 C18 C24 -2.7(5) . . . . ?

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2280516'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;Universty Rennes
France
;
_audit_update_record             
;
2023-08-29 deposited with the CCDC.	2023-08-30 downloaded from the CCDC.
;

_audit_creation_date             2021-11-29T16:07:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C8 H4 N2 Se2'
_chemical_formula_moiety         'C8 H4 N2 Se2'
_chemical_formula_weight         286.05

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_Int_Tables_number      62
loop_
_symmetry_equiv_pos_as_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                   11.563(6)
_cell_length_b                   17.139(8)
_cell_length_c                   4.8436(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     959.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    894
_cell_measurement_theta_min      3.52
_cell_measurement_theta_max      24.6
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.979
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    7.648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.582
_exptl_absorpt_correction_T_max  0.858

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.3714  0.7455                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------# 
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector                 CCD-LDI-APEX2
_diffrn_orient_matrix_ub_11      -0.063412
_diffrn_orient_matrix_ub_12      -0.039673
_diffrn_orient_matrix_ub_13      0.00171
_diffrn_orient_matrix_ub_21      -0.058812
_diffrn_orient_matrix_ub_22      0.042775
_diffrn_orient_matrix_ub_23      -0.002105
_diffrn_orient_matrix_ub_31      0.000075
_diffrn_orient_matrix_ub_32      -0.000765
_diffrn_orient_matrix_ub_33      -0.20644
_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0792
_diffrn_reflns_av_unetI/netI     0.0805
_diffrn_reflns_number            5309
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.524
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_reflns_Friedel_coverage         0
_reflns_number_total             1132
_reflns_number_gt                672
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1224P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1132
_refine_ls_number_parameters     58
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0688
_refine_ls_wR_factor_ref         0.2156
_refine_ls_wR_factor_gt          0.1798
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.056
_refine_diff_density_min         -1.424
_refine_diff_density_rms         0.24

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
C1 C 0.4706(7) 0.6804(4) 0.8553(17) 0.0441(19) Uani 1 1 d . . . . .
C2 C 0.4280(8) 0.75 0.744(2) 0.045(3) Uani 1 2 d S T P . .
H2 H 0.3737 0.75 0.6028 0.054 Uiso 1 2 calc R U P . .
C3 C 0.5956(11) 0.75 1.155(3) 0.067(4) Uani 1 2 d S T P . .
H3 H 0.6531 0.75 1.2896 0.081 Uiso 1 2 calc R U P . .
C4 C 0.5543(7) 0.6806(5) 1.059(2) 0.055(2) Uani 1 1 d . . . . .
H4 H 0.5821 0.6338 1.1302 0.066 Uiso 1 1 calc R U . . .
C5 C 0.2768(7) 0.5801(4) 0.854(2) 0.051(2) Uani 1 1 d . . . . .
N1 N 0.1865(6) 0.5769(4) 0.947(2) 0.070(2) Uani 1 1 d . . . . .
Se1 Se 0.42284(8) 0.58108(5) 0.6964(3) 0.0609(5) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C4 1.382(12) . ?
C1 C2 1.397(10) . ?
C1 Se1 1.949(8) . ?
C2 C1 1.397(10) 7_575 ?
C2 H2 0.93 . ?
C3 C4 1.363(11) 7_575 ?
C3 C4 1.363(11) . ?
C3 H3 0.93 . ?
C4 H4 0.93 . ?
C5 N1 1.138(11) . ?
C5 Se1 1.855(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C1 C2 121.3(8) . . ?
C4 C1 Se1 118.9(7) . . ?
C2 C1 Se1 119.6(7) . . ?
C1 C2 C1 117.1(11) 7_575 . ?
C1 C2 H2 121.4 7_575 . ?
C1 C2 H2 121.4 . . ?
C4 C3 C4 121.4(12) 7_575 . ?
C4 C3 H3 119.3 7_575 . ?
C4 C3 H3 119.3 . . ?
C3 C4 C1 119.4(9) . . ?
C3 C4 H4 120.3 . . ?
C1 C4 H4 120.3 . . ?
N1 C5 Se1 177.5(8) . . ?
C5 Se1 C1 95.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C1 C2 C1 -2.2(15) . . . 7_575 ?
Se1 C1 C2 C1 -176.2(5) . . . 7_575 ?
C4 C3 C4 C1 1(2) 7_575 . . . ?
C2 C1 C4 C3 0.4(15) . . . . ?
Se1 C1 C4 C3 174.4(9) . . . . ?

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2280518'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;Universty Rennes
France
;
_audit_update_record             
;
2023-08-29 deposited with the CCDC.	2023-08-30 downloaded from the CCDC.
;

_audit_creation_date             2023-01-17T17:17:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C8 H4 N2 Se2'
_chemical_formula_moiety         'C8 H4 N2 Se2'
_chemical_formula_weight         286.05

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1170(12)
_cell_length_b                   4.0552(5)
_cell_length_c                   11.8113(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.910(5)
_cell_angle_gamma                90
_cell_volume                     434.36(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3122
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.44
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    2.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             268

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    8.451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.608
_exptl_absorpt_correction_T_max  0.776

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.5288  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
# Ratio of Min/Max transmission:               0.7092                          #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      0.07731
_diffrn_orient_matrix_ub_12      0.167751
_diffrn_orient_matrix_ub_13      0.02425
_diffrn_orient_matrix_ub_21      0.075039
_diffrn_orient_matrix_ub_22      -0.13529
_diffrn_orient_matrix_ub_23      -0.035161
_diffrn_orient_matrix_ub_31      -0.0235
_diffrn_orient_matrix_ub_32      0.119864
_diffrn_orient_matrix_ub_33      -0.073625
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_number            4064
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.934
_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.966
_reflns_Friedel_coverage         0
_reflns_number_total             958
_reflns_number_gt                850
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0119P)²+0.3115P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         958
_refine_ls_number_parameters     55
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0184
_refine_ls_wR_factor_ref         0.0435
_refine_ls_wR_factor_gt          0.0422
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.084

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
C1 C 0.4686(2) 0.3229(5) 0.39920(16) 0.0176(4) Uani 1 1 d . . . . .
H1 H 0.4467 0.2023 0.3306 0.021 Uiso 1 1 calc R U . . .
C2 C 0.35738(18) 0.3974(4) 0.46758(15) 0.0146(3) Uani 1 1 d . . . . .
C3 C 0.3878(2) 0.5734(5) 0.56770(15) 0.0171(4) Uani 1 1 d . . . . .
H3 H 0.3111 0.6231 0.6136 0.021 Uiso 1 1 calc R U . . .
C4 C 0.15213(19) 0.3519(5) 0.27709(16) 0.0174(3) Uani 1 1 d . . . . .
N1 N 0.14594(17) 0.4140(5) 0.18167(13) 0.0251(4) Uani 1 1 d . . . . .
Se1 Se 0.15770(2) 0.24408(4) 0.42941(2) 0.01652(9) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C3 1.392(3) 3_666 ?
C1 C2 1.393(2) . ?
C1 H1 0.95 . ?
C2 C3 1.384(2) . ?
C2 Se1 1.9327(17) . ?
C3 C1 1.392(3) 3_666 ?
C3 H3 0.95 . ?
C4 N1 1.150(2) . ?
C4 Se1 1.8471(19) . ?

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
C3 C1 C2 119.42(17) 3_666 . ?
C3 C1 H1 120.3 3_666 . ?
C2 C1 H1 120.3 . . ?
C3 C2 C1 120.87(16) . . ?
C3 C2 Se1 117.79(12) . . ?
C1 C2 Se1 121.29(13) . . ?
C2 C3 C1 119.72(16) . 3_666 ?
C2 C3 H3 120.1 . . ?
C1 C3 H3 120.1 3_666 . ?
N1 C4 Se1 178.38(18) . . ?
C4 Se1 C2 94.69(8) . . ?

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
C3 C1 C2 C3 0.1(3) 3_666 . . . ?
C3 C1 C2 Se1 -177.34(13) 3_666 . . . ?
C1 C2 C3 C1 -0.1(3) . . . 3_666 ?
Se1 C2 C3 C1 177.43(14) . . . 3_666 ?

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2280517'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;Universty Rennes
France
;
_audit_update_record             
;
2023-08-29 deposited with the CCDC.	2023-08-30 downloaded from the CCDC.
;

_audit_creation_date             2021-12-20T13:37:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C6 H2 N2 S Se2'
_chemical_formula_moiety         'C6 H2 N2 S Se2'
_chemical_formula_weight         292.08

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_Int_Tables_number      62
loop_
_symmetry_equiv_pos_as_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                   11.2833(19)
_cell_length_b                   18.088(3)
_cell_length_c                   4.0560(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     827.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5799
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.58
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    2.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    9.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.585
_exptl_absorpt_correction_T_max  0.695

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.3875  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
# Ratio of Min/Max transmission:               0.5197                          #
#------------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 CMOS-PHOTON70
_diffrn_orient_matrix_ub_11      -0.180993
_diffrn_orient_matrix_ub_12      -0.03354
_diffrn_orient_matrix_ub_13      -0.031169
_diffrn_orient_matrix_ub_21      0.151089
_diffrn_orient_matrix_ub_22      -0.001034
_diffrn_orient_matrix_ub_23      -0.043683
_diffrn_orient_matrix_ub_31      0.0721
_diffrn_orient_matrix_ub_32      -0.082029
_diffrn_orient_matrix_ub_33      0.013295
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_number            6457
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.611
_diffrn_reflns_theta_max         27.579
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             990
_reflns_number_gt                935
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0217P)²+0.4785P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         990
_refine_ls_number_parameters     52
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0194
_refine_ls_R_factor_gt           0.0182
_refine_ls_wR_factor_ref         0.0453
_refine_ls_wR_factor_gt          0.0449
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.097

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
S S 0.1246 0.1234 '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'

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
C1 C 0.54891(16) 0.68223(9) 0.3161(4) 0.0164(3) Uani 1 1 d . . . . .
C2 C 0.45498(15) 0.71068(9) 0.4807(4) 0.0189(3) Uani 1 1 d . . . . .
H2 H 0.3958 0.6814 0.5844 0.023 Uiso 1 1 calc R U . . .
C3 C 0.72846(16) 0.57890(8) 0.4115(4) 0.0194(3) Uani 1 1 d . . . . .
N1 N 0.82257(14) 0.57616(8) 0.5166(5) 0.0262(4) Uani 1 1 d . . . . .
S1 S 0.63837(6) 0.75 0.15172(16) 0.01875(14) Uani 1 2 d S T P . .
Se1 Se 0.57720(2) 0.58028(2) 0.23117(4) 0.01791(9) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.354(2) . ?
C1 S1 1.7222(18) . ?
C1 Se1 1.9029(17) . ?
C2 C2 1.422(3) 7_575 ?
C2 H2 0.95 . ?
C3 N1 1.145(2) . ?
C3 Se1 1.8571(19) . ?
S1 C1 1.7222(18) 7_575 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 S1 112.28(13) . . ?
C2 C1 Se1 126.07(13) . . ?
S1 C1 Se1 121.42(10) . . ?
C1 C2 C2 112.33(10) . 7_575 ?
C1 C2 H2 123.8 . . ?
C2 C2 H2 123.8 7_575 . ?
N1 C3 Se1 177.83(16) . . ?
C1 S1 C1 90.75(12) . 7_575 ?
C3 Se1 C1 95.50(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
S1 C1 C2 C2 -0.93(13) . . . 7_575 ?
Se1 C1 C2 C2 -175.48(9) . . . 7_575 ?
C2 C1 S1 C1 1.23(18) . . . 7_575 ?
Se1 C1 S1 C1 176.06(4) . . . 7_575 ?

####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2280519'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;Universty Rennes
France
;
_audit_update_record             
;
2023-08-29 deposited with the CCDC.	2023-08-30 downloaded from the CCDC.
;

_audit_creation_date             2023-08-29T13:07:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C34 H23 N7 Se4'
_chemical_formula_moiety         'C6 H5 N, C12 H10 N2, 2(C8 H4 N2 Se2)'
_chemical_formula_weight         845.43

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4494(15)
_cell_length_b                   9.201(2)
_cell_length_c                   12.306(3)
_cell_angle_alpha                74.580(8)
_cell_angle_beta                 89.306(7)
_cell_angle_gamma                88.669(7)
_cell_volume                     812.9(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9930
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      27.45
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.55
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.652
_exptl_absorpt_correction_T_max  0.872

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.4258  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
# Ratio of Min/Max transmission:               0.5711                          #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 CMOS-PHOTON70
_diffrn_orient_matrix_ub_11      -0.024956
_diffrn_orient_matrix_ub_12      -0.054494
_diffrn_orient_matrix_ub_13      0.080356
_diffrn_orient_matrix_ub_21      0.052549
_diffrn_orient_matrix_ub_22      -0.094857
_diffrn_orient_matrix_ub_23      -0.013264
_diffrn_orient_matrix_ub_31      0.121023
_diffrn_orient_matrix_ub_32      0.027354
_diffrn_orient_matrix_ub_33      0.021753
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_number            16229
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.475
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.875
_diffrn_measured_fraction_theta_max 0.887
_diffrn_reflns_Laue_measured_fraction_full 0.875
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_point_group_measured_fraction_full 0.875
_diffrn_reflns_point_group_measured_fraction_max 0.887
_reflns_Friedel_coverage         0
_reflns_number_total             3325
_reflns_number_gt                2964
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0356P)²+0.4149P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3325
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.032
_refine_ls_wR_factor_ref         0.0783
_refine_ls_wR_factor_gt          0.0759
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.136
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.58
_refine_diff_density_rms         0.112

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
C1 C 0.5011(3) 0.0847(2) 0.16000(16) 0.0185(4) Uani 1 1 d . . . . .
C2 C 0.6711(3) 0.0909(2) 0.11138(15) 0.0189(4) Uani 1 1 d . . . . .
H2 H 0.727316 0.003453 0.098016 0.023 Uiso 1 1 calc R U . . .
C3 C 0.7566(3) 0.2286(2) 0.08289(17) 0.0202(4) Uani 1 1 d . . . . .
C4 C 0.6761(3) 0.3583(2) 0.09951(18) 0.0243(4) Uani 1 1 d . . . . .
H4 H 0.736942 0.451389 0.079404 0.029 Uiso 1 1 calc R U . . .
C5 C 0.5049(3) 0.3496(2) 0.14607(18) 0.0241(4) Uani 1 1 d . . . . .
H5 H 0.446942 0.438165 0.156282 0.029 Uiso 1 1 calc R U . . .
C6 C 0.4171(3) 0.2128(2) 0.17801(17) 0.0209(4) Uani 1 1 d . . . . .
H6 H 0.301169 0.207013 0.211712 0.025 Uiso 1 1 calc R U . . .
C7 C 0.5354(3) -0.2161(2) 0.15290(19) 0.0249(4) Uani 1 1 d . . . . .
C8 C 0.9402(3) 0.3701(3) -0.11153(19) 0.0286(5) Uani 1 1 d . . . . .
C9A C 0.957(2) 0.8841(10) 0.3215(12) 0.0236(14) Uani 0.518(3) 1 d . . P A 1
H9A H 1.008456 0.804366 0.295056 0.028 Uiso 0.518(3) 1 calc R U P A 1
C10A C 0.8025(8) 0.8594(6) 0.3838(5) 0.0226(9) Uani 0.518(3) 1 d . . P A 1
H10A H 0.749576 0.762891 0.400951 0.027 Uiso 0.518(3) 1 calc R U P A 1
C11A C 0.7220(7) 0.9739(6) 0.4223(4) 0.0173(7) Uani 0.518(3) 1 d . . P A 1
C12A C 0.8089(8) 1.1108(6) 0.3986(5) 0.0224(9) Uani 0.518(3) 1 d . . P A 1
H12A H 0.761402 1.192123 0.424763 0.027 Uiso 0.518(3) 1 calc R U P A 1
C13A C 0.9660(16) 1.1263(12) 0.3360(11) 0.0238(13) Uani 0.518(3) 1 d . . P A 1
H13A H 1.026024 1.21962 0.320143 0.029 Uiso 0.518(3) 1 calc R U P A 1
N3A N 1.037(2) 1.0153(18) 0.2970(17) 0.019(2) Uani 0.518(3) 1 d . . P A 1
C14A C 0.5517(6) 0.9476(5) 0.4858(3) 0.0234(6) Uani 0.518(3) 1 d . . P A 1
H14A H 0.511712 0.846681 0.508769 0.028 Uiso 0.518(3) 1 calc R U P A 1
C9B C 0.945(2) 0.9254(12) 0.3257(13) 0.0236(14) Uani 0.482(3) 1 d . . P A 2
H9B H 0.977574 0.840497 0.299049 0.028 Uiso 0.482(3) 1 calc R U P A 2
C10B C 0.7827(9) 0.9162(8) 0.3906(5) 0.0226(9) Uani 0.482(3) 1 d . . P A 2
H10B H 0.711928 0.828341 0.407552 0.027 Uiso 0.482(3) 1 calc R U P A 2
C11B C 0.7336(7) 1.0410(6) 0.4276(4) 0.0173(7) Uani 0.482(3) 1 d . . P A 2
C12B C 0.8484(9) 1.1645(6) 0.4029(5) 0.0224(9) Uani 0.482(3) 1 d . . P A 2
H12B H 0.821493 1.249932 0.430166 0.027 Uiso 0.482(3) 1 calc R U P A 2
C13B C 1.0016(19) 1.1605(14) 0.3383(13) 0.0238(13) Uani 0.482(3) 1 d . . P A 2
H13B H 1.073946 1.24748 0.320885 0.029 Uiso 0.482(3) 1 calc R U P A 2
N3B N 1.056(3) 1.046(2) 0.299(2) 0.024(3) Uani 0.482(3) 1 d . . P A 2
C14B C 0.5665(6) 1.0488(5) 0.4918(4) 0.0234(6) Uani 0.482(3) 1 d . . P A 2
H14B H 0.552726 1.131113 0.524426 0.028 Uiso 0.482(3) 1 calc R U P A 2
C16 C 0.6305(10) 0.4981(5) 0.3896(4) 0.0310(10) Uani 0.5 1 d . . P B 3
H16 H 0.679222 0.489718 0.319802 0.037 Uiso 0.5 1 calc R U P B 3
C15 C 0.4439(14) 0.5072(8) 0.4042(6) 0.0367(16) Uani 0.5 1 d . . P B 3
H15 H 0.369117 0.503739 0.342959 0.044 Uiso 0.5 1 calc R U P B 3
C17 C 0.7442(8) 0.5015(5) 0.4780(4) 0.0254(9) Uani 0.5 1 d . . P B 3
C18 C 0.6600(10) 0.5135(6) 0.5789(4) 0.0301(11) Uani 0.5 1 d . . P B 3
H18 H 0.729996 0.5157 0.642469 0.036 Uiso 0.5 1 calc R U P B 3
C19 C 0.4759(13) 0.5220(8) 0.5841(6) 0.0347(14) Uani 0.5 1 d . . P B 3
H19 H 0.422229 0.529498 0.652928 0.042 Uiso 0.5 1 calc R U P B 3
C20 C 0.9474(6) 0.4935(4) 0.4607(3) 0.0242(8) Uani 0.5 1 d . . P B 3
H20 H 0.995451 0.479161 0.392397 0.029 Uiso 0.5 1 calc R U P B 3
N4 N 0.3664(8) 0.5204(5) 0.4984(5) 0.0401(11) Uani 0.5 1 d . . P B 3
N1 N 0.6403(3) -0.2894(2) 0.1213(2) 0.0333(5) Uani 1 1 d . . . . .
N2 N 0.9039(4) 0.4581(3) -0.1936(2) 0.0547(7) Uani 1 1 d . . . . .
Se1 Se 0.36648(3) -0.09960(2) 0.20470(2) 0.02282(9) Uani 1 1 d . . . . .
Se2 Se 0.99760(3) 0.23328(2) 0.02240(2) 0.02520(10) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.390(3) . ?
C1 C6 1.390(3) . ?
C1 Se1 1.937(2) . ?
C2 C3 1.389(3) . ?
C2 H2 0.95 . ?
C3 C4 1.385(3) . ?
C3 Se2 1.932(2) . ?
C4 C5 1.387(3) . ?
C4 H4 0.95 . ?
C5 C6 1.392(3) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 N1 1.151(3) . ?
C7 Se1 1.849(2) . ?
C8 N2 1.144(3) . ?
C8 Se2 1.837(2) . ?
C9A N3A 1.318(17) . ?
C9A C10A 1.364(17) . ?
C9A H9A 0.95 . ?
C10A C11A 1.387(6) . ?
C10A H10A 0.95 . ?
C11A C12A 1.389(6) . ?
C11A C14A 1.473(7) . ?
C12A C13A 1.382(14) . ?
C12A H12A 0.95 . ?
C13A N3A 1.334(19) . ?
C13A H13A 0.95 . ?
C14A C14A 1.335(9) 2_676 ?
C14A H14A 0.95 . ?
C9B N3B 1.37(2) . ?
C9B C10B 1.431(18) . ?
C9B H9B 0.95 . ?
C10B C11B 1.383(7) . ?
C10B H10B 0.95 . ?
C11B C12B 1.403(7) . ?
C11B C14B 1.478(7) . ?
C12B C13B 1.389(16) . ?
C12B H12B 0.95 . ?
C13B N3B 1.33(2) . ?
C13B H13B 0.95 . ?
C14B C14B 1.330(9) 2_676 ?
C14B H14B 0.95 . ?
C16 C17 1.393(7) . ?
C16 C15 1.403(10) . ?
C16 H16 0.95 . ?
C16 H19 0.758(9) 2_666 ?
C15 N4 1.322(10) . ?
C15 H15 0.95 . ?
C15 H19 1.302(10) 2_666 ?
C17 C18 1.414(7) . ?
C17 C20 1.529(7) . ?
C18 C19 1.374(9) . ?
C18 H18 0.95 . ?
C19 N4 1.345(9) . ?
C19 H19 0.95 . ?
C20 C20 1.283(8) 2_766 ?
C20 H20 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.17(18) . . ?
C2 C1 Se1 122.69(14) . . ?
C6 C1 Se1 116.14(15) . . ?
C3 C2 C1 118.11(18) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C4 C3 C2 122.03(19) . . ?
C4 C3 Se2 120.36(15) . . ?
C2 C3 Se2 117.58(15) . . ?
C3 C4 C5 118.70(19) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C6 120.78(19) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 119.18(19) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N1 C7 Se1 179.5(2) . . ?
N2 C8 Se2 178.3(2) . . ?
N3A C9A C10A 121.9(10) . . ?
N3A C9A H9A 119 . . ?
C10A C9A H9A 119 . . ?
C9A C10A C11A 120.6(6) . . ?
C9A C10A H10A 119.7 . . ?
C11A C10A H10A 119.7 . . ?
C10A C11A C12A 117.2(5) . . ?
C10A C11A C14A 120.1(5) . . ?
C12A C11A C14A 122.7(5) . . ?
C13A C12A C11A 118.6(6) . . ?
C13A C12A H12A 120.7 . . ?
C11A C12A H12A 120.7 . . ?
N3A C13A C12A 122.6(9) . . ?
N3A C13A H13A 118.7 . . ?
C12A C13A H13A 118.7 . . ?
C9A N3A C13A 119.0(13) . . ?
C14A C14A C11A 126.1(5) 2_676 . ?
C14A C14A H14A 117 2_676 . ?
C11A C14A H14A 117 . . ?
N3B C9B C10B 125.6(12) . . ?
N3B C9B H9B 117.2 . . ?
C10B C9B H9B 117.2 . . ?
C11B C10B C9B 117.0(7) . . ?
C11B C10B H10B 121.5 . . ?
C9B C10B H10B 121.5 . . ?
C10B C11B C12B 118.2(5) . . ?
C10B C11B C14B 122.7(5) . . ?
C12B C11B C14B 119.1(5) . . ?
C13B C12B C11B 119.4(6) . . ?
C13B C12B H12B 120.3 . . ?
C11B C12B H12B 120.3 . . ?
N3B C13B C12B 125.7(10) . . ?
N3B C13B H13B 117.1 . . ?
C12B C13B H13B 117.1 . . ?
C13B N3B C9B 114.0(17) . . ?
C14B C14B C11B 126.0(6) 2_676 . ?
C14B C14B H14B 117 2_676 . ?
C11B C14B H14B 117 . . ?
C17 C16 C15 119.7(6) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
N4 C15 C16 123.6(7) . . ?
N4 C15 H15 118.2 . . ?
C16 C15 H15 118.2 . . ?
C16 C17 C18 116.3(6) . . ?
C16 C17 C20 119.3(5) . . ?
C18 C17 C20 124.4(5) . . ?
C19 C18 C17 119.3(6) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
N4 C19 C18 124.4(7) . . ?
N4 C19 H19 117.8 . . ?
C18 C19 H19 117.8 . . ?
C20 C20 C17 119.5(6) 2_766 . ?
C20 C20 H20 120.3 2_766 . ?
C17 C20 H20 120.3 . . ?
C15 N4 C19 116.7(6) . . ?
C7 Se1 C1 95.22(9) . . ?
C8 Se2 C3 94.29(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.1(3) . . . . ?
Se1 C1 C2 C3 -179.70(14) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C1 C2 C3 Se2 176.97(14) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
Se2 C3 C4 C5 -178.19(15) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
Se1 C1 C6 C5 -178.90(16) . . . . ?
C4 C5 C6 C1 -1.7(3) . . . . ?
N3A C9A C10A C11A 1(2) . . . . ?
C9A C10A C11A C12A -2.5(10) . . . . ?
C9A C10A C11A C14A 177.7(8) . . . . ?
C10A C11A C12A C13A 1.8(10) . . . . ?
C14A C11A C12A C13A -178.4(8) . . . . ?
C11A C12A C13A N3A 0.5(19) . . . . ?
C10A C9A N3A C13A 1(3) . . . . ?
C12A C13A N3A C9A -2(3) . . . . ?
C10A C11A C14A C14A -170.3(6) . . . 2_676 ?
C12A C11A C14A C14A 9.9(8) . . . 2_676 ?
N3B C9B C10B C11B 1(2) . . . . ?
C9B C10B C11B C12B -2.4(10) . . . . ?
C9B C10B C11B C14B 177.8(8) . . . . ?
C10B C11B C12B C13B 3.0(11) . . . . ?
C14B C11B C12B C13B -177.2(9) . . . . ?
C11B C12B C13B N3B -2(2) . . . . ?
C12B C13B N3B C9B 1(3) . . . . ?
C10B C9B N3B C13B 0(3) . . . . ?
C10B C11B C14B C14B -10.0(9) . . . 2_676 ?
C12B C11B C14B C14B 170.1(6) . . . 2_676 ?
C17 C16 C15 N4 0.6(9) . . . . ?
C15 C16 C17 C18 0.3(7) . . . . ?
C15 C16 C17 C20 -179.2(5) . . . . ?
C16 C17 C18 C19 -0.4(7) . . . . ?
C20 C17 C18 C19 179.1(5) . . . . ?
C17 C18 C19 N4 -0.3(9) . . . . ?
C16 C17 C20 C20 175.5(5) . . . 2_766 ?
C18 C17 C20 C20 -4.0(8) . . . 2_766 ?
C16 C15 N4 C19 -1.3(10) . . . . ?
C18 C19 N4 C15 1.2(10) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2280520'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;Universty Rennes
France
;
_audit_update_record             
;
2023-08-29 deposited with the CCDC.	2023-08-30 downloaded from the CCDC.
;

_audit_creation_date             2021-12-20T15:33:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C20 H14 N4 Se2'
_chemical_formula_moiety         'C12 H10 N2, C8 H4 N2 Se2'
_chemical_formula_weight         468.27

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.8342(15)
_cell_length_b                   14.079(3)
_cell_length_c                   7.6447(14)
_cell_angle_alpha                90
_cell_angle_beta                 110.592(7)
_cell_angle_gamma                90
_cell_volume                     890.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8383
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.5
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_T_max  0.779

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.6228  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
# Ratio of Min/Max transmission:               0.8353                          #
#------------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 CMOS-PHOTON70
_diffrn_orient_matrix_ub_11      0.05059
_diffrn_orient_matrix_ub_12      0.065905
_diffrn_orient_matrix_ub_13      0.025498
_diffrn_orient_matrix_ub_21      0.130249
_diffrn_orient_matrix_ub_22      -0.025516
_diffrn_orient_matrix_ub_23      0.034414
_diffrn_orient_matrix_ub_31      -0.001509
_diffrn_orient_matrix_ub_32      0.007095
_diffrn_orient_matrix_ub_33      -0.113083
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.026
_diffrn_reflns_number            8351
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.463
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.983
_reflns_Friedel_coverage         0
_reflns_number_total             2014
_reflns_number_gt                1906
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0230P)²+0.4592P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2014
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.021
_refine_ls_R_factor_gt           0.0194
_refine_ls_wR_factor_ref         0.0507
_refine_ls_wR_factor_gt          0.0498
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.52
_refine_diff_density_rms         0.077

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
C1 C 0.08922(19) 0.50373(10) 0.3829(2) 0.0127(3) Uani 1 1 d . . . . .
C2 C -0.01345(17) 0.57869(10) 0.38347(19) 0.0136(3) Uani 1 1 d . . . . .
H2 H -0.0222 0.632 0.3043 0.016 Uiso 1 1 calc R U . . .
C3 C 0.10311(17) 0.42508(10) 0.49926(19) 0.0136(3) Uani 1 1 d . . . . .
H3 H 0.1737 0.3743 0.4982 0.016 Uiso 1 1 calc R U . . .
C4 C 0.16519(18) 0.38577(11) 0.1356(2) 0.0167(3) Uani 1 1 d . . . . .
C5 C 0.4480(2) 0.69516(11) 0.4948(2) 0.0194(3) Uani 1 1 d . . . . .
H5 H 0.5033 0.6388 0.5505 0.023 Uiso 1 1 calc R U . . .
C6 C 0.52361(18) 0.78189(11) 0.5543(2) 0.0178(3) Uani 1 1 d . . . . .
H6 H 0.6277 0.784 0.649 0.021 Uiso 1 1 calc R U . . .
C7 C 0.44619(18) 0.86582(11) 0.4746(2) 0.0141(3) Uani 1 1 d . . . . .
C8 C 0.29272(18) 0.85727(11) 0.3370(2) 0.0170(3) Uani 1 1 d . . . . .
H8 H 0.2345 0.9123 0.2787 0.02 Uiso 1 1 calc R U . . .
C9 C 0.22652(19) 0.76803(12) 0.2866(2) 0.0185(3) Uani 1 1 d . . . . .
H9 H 0.1222 0.7638 0.1927 0.022 Uiso 1 1 calc R U . . .
C10 C 0.52677(18) 0.95777(12) 0.5370(2) 0.0161(3) Uani 1 1 d . . . . .
H10 H 0.6262 0.9566 0.6397 0.019 Uiso 1 1 calc R U . . .
N1 N 0.14084(18) 0.30961(10) 0.0793(2) 0.0244(3) Uani 1 1 d . . . . .
N2 N 0.30090(16) 0.68693(10) 0.36253(18) 0.0181(3) Uani 1 1 d . . . . .
Se1 Se 0.21653(2) 0.51121(2) 0.22306(2) 0.01388(7) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.393(2) . ?
C1 C3 1.399(2) . ?
C1 Se1 1.9326(16) . ?
C2 C3 1.391(2) 3_566 ?
C2 H2 0.95 . ?
C3 C2 1.391(2) 3_566 ?
C3 H3 0.95 . ?
C4 N1 1.147(2) . ?
C4 Se1 1.8863(16) . ?
C5 N2 1.342(2) . ?
C5 C6 1.389(2) . ?
C5 H5 0.95 . ?
C6 C7 1.394(2) . ?
C6 H6 0.95 . ?
C7 C8 1.399(2) . ?
C7 C10 1.474(2) . ?
C8 C9 1.382(2) . ?
C8 H8 0.95 . ?
C9 N2 1.343(2) . ?
C9 H9 0.95 . ?
C10 C10 1.330(3) 3_676 ?
C10 H10 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C3 120.62(14) . . ?
C2 C1 Se1 119.03(11) . . ?
C3 C1 Se1 120.33(11) . . ?
C3 C2 C1 119.50(14) 3_566 . ?
C3 C2 H2 120.2 3_566 . ?
C1 C2 H2 120.2 . . ?
C2 C3 C1 119.87(14) 3_566 . ?
C2 C3 H3 120.1 3_566 . ?
C1 C3 H3 120.1 . . ?
N1 C4 Se1 176.37(15) . . ?
N2 C5 C6 123.32(15) . . ?
N2 C5 H5 118.3 . . ?
C6 C5 H5 118.3 . . ?
C5 C6 C7 119.77(14) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C8 116.92(14) . . ?
C6 C7 C10 119.77(13) . . ?
C8 C7 C10 123.31(14) . . ?
C9 C8 C7 119.41(14) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
N2 C9 C8 123.89(14) . . ?
N2 C9 H9 118.1 . . ?
C8 C9 H9 118.1 . . ?
C10 C10 C7 126.06(18) 3_676 . ?
C10 C10 H10 117 3_676 . ?
C7 C10 H10 117 . . ?
C5 N2 C9 116.69(14) . . ?
C4 Se1 C1 92.99(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
C3 C1 C2 C3 -0.2(2) . . . 3_566 ?
Se1 C1 C2 C3 -178.69(10) . . . 3_566 ?
C2 C1 C3 C2 0.2(2) . . . 3_566 ?
Se1 C1 C3 C2 178.67(10) . . . 3_566 ?
N2 C5 C6 C7 -0.3(3) . . . . ?
C5 C6 C7 C8 0.4(2) . . . . ?
C5 C6 C7 C10 -179.65(15) . . . . ?
C6 C7 C8 C9 -0.3(2) . . . . ?
C10 C7 C8 C9 179.77(15) . . . . ?
C7 C8 C9 N2 0.1(3) . . . . ?
C6 C7 C10 C10 174.1(2) . . . 3_676 ?
C8 C7 C10 C10 -6.0(3) . . . 3_676 ?
C6 C5 N2 C9 0.1(2) . . . . ?
C8 C9 N2 C5 0.0(2) . . . . ?

