# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

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

data_Y524
_database_code_depnum_ccdc_archive 'CCDC 2063244'
loop_
_audit_author_name
_audit_author_address
Roisnel
;Institut des sciences chimiques de Rennes
France
;
_audit_update_record             
;
2021-02-16 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;


#----------------------------------------------------------------------------#
#                              CHEMICAL_INFORMATION                          #
#----------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H10 N2 S4 Se'
_chemical_formula_sum            'C10 H10 N2 S4 Se'
_chemical_formula_weight         365.40
_chemical_compound_source        'synthesis as described'

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


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
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                   8.7866(11)
_cell_length_b                   12.3894(9)
_cell_length_c                   12.6125(12)
_cell_angle_alpha                90
_cell_angle_beta                 94.728(5)
_cell_angle_gamma                90
_cell_volume                     1368.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    295
_cell_measurement_reflns_used    7652
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      27.42
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.130
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             728
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    3.332
_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  0.354
_exptl_absorpt_correction_T_max  0.648

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

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_reflns_av_r_equivalents  0.0438
_diffrn_reflns_av_uneti/neti     0.0449
_diffrn_reflns_number            11626
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.181
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             3133
_reflns_number_gt                2490
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2014)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2016)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0448P)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         3133
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0876
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.688
_refine_diff_density_rms         0.070

#...............................................................................
# .RES SHELXL file: job.res
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file .............................................
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                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 0.0000 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'
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 0.0634(3) 0.6597(2) 0.4206(2) 0.0362(5) Uani 1 1 d . . . . .
N2 N 0.0770(2) 0.57054(16) 0.35970(16) 0.0362(5) Uani 1 1 d . . . . .
C3 C -0.0037(3) 0.5555(2) 0.2534(2) 0.0473(7) Uani 1 1 d . . . . .
H3A H -0.0943 0.6033 0.2461 0.057 Uiso 1 1 calc R U . . .
H3B H -0.0396 0.4800 0.2459 0.057 Uiso 1 1 calc R U . . .
C4 C 0.0977(5) 0.5806(3) 0.1671(2) 0.0684(10) Uani 1 1 d . . . . .
H4A H 0.1343 0.6551 0.1750 0.103 Uiso 1 1 calc R U . . .
H4B H 0.0403 0.5720 0.0977 0.103 Uiso 1 1 calc R U . . .
H4C H 0.1851 0.5312 0.1722 0.103 Uiso 1 1 calc R U . . .
C5 C 0.1753(3) 0.49373(19) 0.40615(19) 0.0331(5) Uani 1 1 d . . . . .
C6 C 0.2409(3) 0.51978(17) 0.50409(19) 0.0316(5) Uani 1 1 d . . . . .
C7 C 0.3433(3) 0.43926(18) 0.54829(19) 0.0318(5) Uani 1 1 d . . . . .
C8 C 0.3575(3) 0.35397(17) 0.4821(2) 0.0331(5) Uani 1 1 d . . . . .
N9 N 0.4458(2) 0.27006(15) 0.52442(16) 0.0332(5) Uani 1 1 d . . . . .
C10 C 0.4745(3) 0.1722(2) 0.4634(2) 0.0408(6) Uani 1 1 d . . . . .
H10A H 0.5719 0.1392 0.4921 0.049 Uiso 1 1 calc R U . . .
H10B H 0.4846 0.1919 0.3883 0.049 Uiso 1 1 calc R U . . .
C11 C 0.3475(4) 0.0911(2) 0.4685(3) 0.0574(8) Uani 1 1 d . . . . .
H11A H 0.3431 0.0667 0.5420 0.086 Uiso 1 1 calc R U . . .
H11B H 0.3667 0.0292 0.4231 0.086 Uiso 1 1 calc R U . . .
H11C H 0.2501 0.1248 0.4436 0.086 Uiso 1 1 calc R U . . .
C12 C 0.5022(3) 0.28626(19) 0.6267(2) 0.0346(5) Uani 1 1 d . . . . .
S1 S -0.04389(10) 0.76771(6) 0.39251(6) 0.0533(2) Uani 1 1 d . . . . .
S2 S 0.17828(8) 0.64636(5) 0.54040(5) 0.03596(16) Uani 1 1 d . . . . .
S3 S 0.44563(8) 0.41431(5) 0.66916(5) 0.03686(16) Uani 1 1 d . . . . .
S4 S 0.61127(9) 0.20257(6) 0.70222(6) 0.0516(2) Uani 1 1 d . . . . .
Se1 Se 0.23840(3) 0.36111(2) 0.35210(2) 0.03885(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 N2 1.356(3) . ?
C1 S1 1.658(3) . ?
C1 S2 1.755(3) . ?
N2 C5 1.383(3) . ?
N2 C3 1.476(3) . ?
C3 C4 1.494(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.358(4) . ?
C5 Se1 1.880(2) . ?
C6 C7 1.425(3) . ?
C6 S2 1.736(2) . ?
C7 C8 1.358(3) . ?
C7 S3 1.733(2) . ?
C8 N9 1.378(3) . ?
C8 Se1 1.873(3) . ?
N9 C12 1.359(3) . ?
N9 C10 1.469(3) . ?
C10 C11 1.506(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 S4 1.658(3) . ?
C12 S3 1.759(2) . ?

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 S1 127.7(2) . . ?
N2 C1 S2 109.84(18) . . ?
S1 C1 S2 122.46(16) . . ?
C1 N2 C5 113.7(2) . . ?
C1 N2 C3 124.0(2) . . ?
C5 N2 C3 122.3(2) . . ?
N2 C3 C4 111.4(3) . . ?
N2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
N2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N2 115.2(2) . . ?
C6 C5 Se1 114.95(18) . . ?
N2 C5 Se1 129.82(19) . . ?
C5 C6 C7 113.3(2) . . ?
C5 C6 S2 109.55(18) . . ?
C7 C6 S2 137.11(19) . . ?
C8 C7 C6 113.0(2) . . ?
C8 C7 S3 109.53(18) . . ?
C6 C7 S3 137.21(18) . . ?
C7 C8 N9 115.2(2) . . ?
C7 C8 Se1 115.34(18) . . ?
N9 C8 Se1 129.08(17) . . ?
C12 N9 C8 113.9(2) . . ?
C12 N9 C10 123.7(2) . . ?
C8 N9 C10 122.4(2) . . ?
N9 C10 C11 111.6(2) . . ?
N9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
N9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N9 C12 S4 126.96(19) . . ?
N9 C12 S3 109.39(18) . . ?
S4 C12 S3 123.63(15) . . ?
C6 S2 C1 91.75(12) . . ?
C7 S3 C12 91.86(12) . . ?
C8 Se1 C5 83.33(10) . . ?

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 N2 C5 -179.5(2) . . . . ?
S2 C1 N2 C5 -0.1(3) . . . . ?
S1 C1 N2 C3 1.0(4) . . . . ?
S2 C1 N2 C3 -179.6(2) . . . . ?
C1 N2 C3 C4 99.2(3) . . . . ?
C5 N2 C3 C4 -80.3(3) . . . . ?
C1 N2 C5 C6 0.3(3) . . . . ?
C3 N2 C5 C6 179.8(2) . . . . ?
C1 N2 C5 Se1 -176.95(19) . . . . ?
C3 N2 C5 Se1 2.6(4) . . . . ?
N2 C5 C6 C7 -179.0(2) . . . . ?
Se1 C5 C6 C7 -1.4(3) . . . . ?
N2 C5 C6 S2 -0.3(3) . . . . ?
Se1 C5 C6 S2 177.32(12) . . . . ?
C5 C6 C7 C8 1.6(3) . . . . ?
S2 C6 C7 C8 -176.6(2) . . . . ?
C5 C6 C7 S3 -172.0(2) . . . . ?
S2 C6 C7 S3 9.8(5) . . . . ?
C6 C7 C8 N9 -175.1(2) . . . . ?
S3 C7 C8 N9 0.3(3) . . . . ?
C6 C7 C8 Se1 -1.1(3) . . . . ?
S3 C7 C8 Se1 174.27(12) . . . . ?
C7 C8 N9 C12 1.0(3) . . . . ?
Se1 C8 N9 C12 -171.94(19) . . . . ?
C7 C8 N9 C10 -179.3(2) . . . . ?
Se1 C8 N9 C10 7.7(4) . . . . ?
C12 N9 C10 C11 95.0(3) . . . . ?
C8 N9 C10 C11 -84.6(3) . . . . ?
C8 N9 C12 S4 179.63(19) . . . . ?
C10 N9 C12 S4 0.0(4) . . . . ?
C8 N9 C12 S3 -1.8(3) . . . . ?
C10 N9 C12 S3 178.54(18) . . . . ?
C5 C6 S2 C1 0.2(2) . . . . ?
C7 C6 S2 C1 178.5(3) . . . . ?
N2 C1 S2 C6 -0.1(2) . . . . ?
S1 C1 S2 C6 179.36(18) . . . . ?
C8 C7 S3 C12 -1.1(2) . . . . ?
C6 C7 S3 C12 172.7(3) . . . . ?
N9 C12 S3 C7 1.7(2) . . . . ?
S4 C12 S3 C7 -179.73(18) . . . . ?
C7 C8 Se1 C5 0.3(2) . . . . ?
N9 C8 Se1 C5 173.3(2) . . . . ?
C6 C5 Se1 C8 0.6(2) . . . . ?
N2 C5 Se1 C8 177.8(3) . . . . ?

#----------------------------------------------------------------------------#
#===END OF CIF FILE FOR Y524                                                 #
#----------------------------------------------------------------------------#
####################################################################### 
# 
# 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_compound7
_database_code_depnum_ccdc_archive 'CCDC 2063245'
loop_
_audit_author_name
_audit_author_address
Roisnel
;Institut des sciences chimiques de Rennes
France
;
_audit_update_record             
;
2021-02-16 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of diffraction experiment: 01 juillet 2020                              #
#------------------------------------------------------------------------------#


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H10 N2 S4 Se2'
_chemical_formula_sum            'C10 H10 N2 S4 Se2'
_chemical_formula_weight         444.36
_chemical_compound_source        'synthesis as described'

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


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.9196(7)
_cell_length_b                   8.7472(7)
_cell_length_c                   20.8069(19)
_cell_angle_alpha                90
_cell_angle_beta                 99.984(3)
_cell_angle_gamma                90
_cell_volume                     1419.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      2.5317
_cell_measurement_theta_max      27.5619
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0249491
_diffrn_orient_matrix_UB_21      0.1214802
_diffrn_orient_matrix_UB_31      0.0325291
_diffrn_orient_matrix_UB_12      0.0506747
_diffrn_orient_matrix_UB_22      -0.0360899
_diffrn_orient_matrix_UB_32      0.0959118
_diffrn_orient_matrix_UB_13      0.0437004
_diffrn_orient_matrix_UB_23      0.0055754
_diffrn_orient_matrix_UB_33      -0.0209910


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

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.055
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.079
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             864
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    5.779
_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  0.479
_exptl_absorpt_correction_T_max  0.728

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

# Software                   : BIS V6.2.1/2016-03-01                           #
# Number of scans            :        3                                        #
# Total number of frames [*] :      478                                        #
# Total length of scans  [*] :   239.00 (deg.)                                 #
# Rotation speed         [*] :    16.00 sec./deg.                              #
# Total exposition time  [*] :      1 h   3.7 min.                             #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
# Measurement mode           : shutterless mode                                #
#                                                                              #
#    Scan  Time(s)  Width  DX (mm)  Frames  Theta  Omega    Phi    Chi   T(K)  #
#..............................................................................#
#                                                                              #
#  1 Omega     8.0   0.50     34.0     176   0.63 269.42 213.02  27.31 150.00  #
#  2 Phi       8.0   0.50     34.0     302   0.27 270.94 344.52  23.00 149.99  #
#  3 Fast      2.0   1.00     34.0     180   0.00 360.00   0.00  54.74 150.00  #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0355
_diffrn_reflns_av_r_equivalents  0.0396
_diffrn_reflns_number            13819
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.532
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             3262
_reflns_number_gt                2975
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'

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

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0216P)²+1.3917P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3262
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0579
_refine_ls_wR_factor_gt          0.0558
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.759
_refine_diff_density_rms         0.095

#------------------------------------------------------------------------------#
#               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 0.0000 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'
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
Se1 Se 0.13578(3) 0.52492(3) 0.58292(2) 0.01644(7) Uani 1 1 d . . . . .
Se2 Se 0.16607(3) 0.78950(3) 0.56528(2) 0.01899(7) Uani 1 1 d . . . . .
S1 S 0.57938(8) 0.35689(7) 0.81434(3) 0.01777(13) Uani 1 1 d . . . . .
S2 S 0.64590(7) 0.56155(6) 0.70691(3) 0.01376(12) Uani 1 1 d . . . . .
S3 S 0.69560(7) 0.67429(6) 0.54759(3) 0.01419(12) Uani 1 1 d . . . . .
S4 S 0.71197(8) 0.84786(6) 0.42450(3) 0.01859(13) Uani 1 1 d . . . . .
C1 C 0.5132(3) 0.4419(2) 0.74256(10) 0.0121(4) Uani 1 1 d . . . . .
N2 N 0.3558(2) 0.4345(2) 0.70398(9) 0.0124(4) Uani 1 1 d . . . . .
C3 C 0.2144(3) 0.3460(2) 0.72337(11) 0.0148(4) Uani 1 1 d . . . . .
H3A H 0.262787 0.260779 0.752090 0.018 Uiso 1 1 calc R U . . .
H3B H 0.143730 0.301311 0.683946 0.018 Uiso 1 1 calc R U . . .
C4 C 0.1019(3) 0.4427(3) 0.75865(12) 0.0199(5) Uani 1 1 d . . . . .
H4A H 0.170277 0.483530 0.798761 0.030 Uiso 1 1 calc R U . . .
H4B H 0.008484 0.379909 0.769654 0.030 Uiso 1 1 calc R U . . .
H4C H 0.053962 0.527417 0.730470 0.030 Uiso 1 1 calc R U . . .
C5 C 0.3412(3) 0.5172(2) 0.64639(10) 0.0131(4) Uani 1 1 d . . . . .
C6 C 0.4862(3) 0.5913(3) 0.63886(10) 0.0124(4) Uani 1 1 d . . . . .
C7 C 0.5099(3) 0.6781(2) 0.58115(10) 0.0123(4) Uani 1 1 d . . . . .
C8 C 0.3863(3) 0.7595(2) 0.54273(11) 0.0130(4) Uani 1 1 d . . . . .
N9 N 0.4387(2) 0.8180(2) 0.48685(9) 0.0127(4) Uani 1 1 d . . . . .
C10 C 0.6039(3) 0.7872(2) 0.48201(11) 0.0132(4) Uani 1 1 d . . . . .
C11 C 0.3199(3) 0.8919(3) 0.43324(11) 0.0171(5) Uani 1 1 d . . . . .
H11A H 0.383035 0.967537 0.411109 0.020 Uiso 1 1 calc R U . . .
H11B H 0.228956 0.946611 0.451197 0.020 Uiso 1 1 calc R U . . .
C12 C 0.2391(4) 0.7722(3) 0.38431(13) 0.0308(7) Uani 1 1 d . . . . .
H12A H 0.329224 0.719289 0.366121 0.046 Uiso 1 1 calc R U . . .
H12B H 0.160278 0.822142 0.349034 0.046 Uiso 1 1 calc R U . . .
H12C H 0.175768 0.698010 0.406259 0.046 Uiso 1 1 calc R U . . .



#------------------------------------------------------------------------------#
#                              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
Se1 C5 1.910(2) . ?
Se1 Se2 2.3620(4) . ?
Se2 C8 1.901(2) . ?
S1 C1 1.669(2) . ?
S2 C1 1.738(2) . ?
S2 C6 1.747(2) . ?
S3 C7 1.734(2) . ?
S3 C10 1.738(2) . ?
S4 C10 1.674(2) . ?
C1 N2 1.362(3) . ?
N2 C5 1.387(3) . ?
N2 C3 1.474(3) . ?
C3 C4 1.508(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.351(3) . ?
C6 C7 1.460(3) . ?
C7 C8 1.354(3) . ?
C8 N9 1.397(3) . ?
N9 C10 1.357(3) . ?
N9 C11 1.478(3) . ?
C11 C12 1.522(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C5 Se1 Se2 92.57(7) . . ?
C8 Se2 Se1 91.46(7) . . ?
C1 S2 C6 91.67(11) . . ?
C7 S3 C10 92.13(11) . . ?
N2 C1 S1 128.26(17) . . ?
N2 C1 S2 109.66(15) . . ?
S1 C1 S2 122.07(13) . . ?
C1 N2 C5 114.54(19) . . ?
C1 N2 C3 121.65(18) . . ?
C5 N2 C3 123.81(19) . . ?
N2 C3 C4 112.32(18) . . ?
N2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
N2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N2 113.9(2) . . ?
C6 C5 Se1 122.81(17) . . ?
N2 C5 Se1 123.33(17) . . ?
C5 C6 C7 125.3(2) . . ?
C5 C6 S2 110.19(16) . . ?
C7 C6 S2 124.45(17) . . ?
C8 C7 C6 125.2(2) . . ?
C8 C7 S3 110.45(16) . . ?
C6 C7 S3 124.07(17) . . ?
C7 C8 N9 113.3(2) . . ?
C7 C8 Se2 121.82(17) . . ?
N9 C8 Se2 124.92(16) . . ?
C10 N9 C8 114.74(18) . . ?
C10 N9 C11 121.81(19) . . ?
C8 N9 C11 123.1(2) . . ?
N9 C10 S4 127.55(17) . . ?
N9 C10 S3 109.37(16) . . ?
S4 C10 S3 123.07(14) . . ?
N9 C11 C12 110.04(19) . . ?
N9 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
N9 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C6 S2 C1 N2 -2.41(16) . . . . ?
C6 S2 C1 S1 178.75(15) . . . . ?
S1 C1 N2 C5 -179.27(17) . . . . ?
S2 C1 N2 C5 2.0(2) . . . . ?
S1 C1 N2 C3 1.3(3) . . . . ?
S2 C1 N2 C3 -177.48(16) . . . . ?
C1 N2 C3 C4 93.2(2) . . . . ?
C5 N2 C3 C4 -86.2(3) . . . . ?
C1 N2 C5 C6 -0.2(3) . . . . ?
C3 N2 C5 C6 179.2(2) . . . . ?
C1 N2 C5 Se1 179.29(15) . . . . ?
C3 N2 C5 Se1 -1.3(3) . . . . ?
N2 C5 C6 C7 175.7(2) . . . . ?
Se1 C5 C6 C7 -3.8(3) . . . . ?
N2 C5 C6 S2 -1.6(2) . . . . ?
Se1 C5 C6 S2 178.85(11) . . . . ?
C1 S2 C6 C5 2.31(18) . . . . ?
C1 S2 C6 C7 -175.09(19) . . . . ?
C5 C6 C7 C8 33.8(4) . . . . ?
S2 C6 C7 C8 -149.2(2) . . . . ?
C5 C6 C7 S3 -139.1(2) . . . . ?
S2 C6 C7 S3 37.9(3) . . . . ?
C10 S3 C7 C8 1.05(18) . . . . ?
C10 S3 C7 C6 174.84(19) . . . . ?
C6 C7 C8 N9 -173.5(2) . . . . ?
S3 C7 C8 N9 0.2(2) . . . . ?
C6 C7 C8 Se2 7.1(3) . . . . ?
S3 C7 C8 Se2 -179.21(11) . . . . ?
C7 C8 N9 C10 -1.9(3) . . . . ?
Se2 C8 N9 C10 177.52(16) . . . . ?
C7 C8 N9 C11 171.3(2) . . . . ?
Se2 C8 N9 C11 -9.3(3) . . . . ?
C8 N9 C10 S4 -175.96(17) . . . . ?
C11 N9 C10 S4 10.8(3) . . . . ?
C8 N9 C10 S3 2.6(2) . . . . ?
C11 N9 C10 S3 -170.65(16) . . . . ?
C7 S3 C10 N9 -2.06(17) . . . . ?
C7 S3 C10 S4 176.58(15) . . . . ?
C10 N9 C11 C12 85.1(3) . . . . ?
C8 N9 C11 C12 -87.6(3) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


