# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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 2190025'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University of Rennes 
France
;
_audit_update_record             
;
2022-10-05 deposited with the CCDC.	2022-10-07 downloaded from the CCDC.
;

_audit_creation_date             2022-03-07T16:04:52-00:00
_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            'C10 H10 S6 Se2'
_chemical_formula_moiety         'C10 H10 S6 Se2'
_chemical_formula_weight         480.46

#----------------------------------------------------------------------------#
#                   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                   15.7509(18)
_cell_length_b                   13.2011(13)
_cell_length_c                   15.8501(16)
_cell_angle_alpha                90
_cell_angle_beta                 105.818(3)
_cell_angle_gamma                90
_cell_volume                     3170.9(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5873
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      27.46
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    2.013
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1872

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

_exptl_absorpt_coefficient_mu    5.433
_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  0.332
_exptl_absorpt_correction_T_max  0.897

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.2645  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
# Ratio of Min/Max transmission:               0.3547                          #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   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      -0.008498
_diffrn_orient_matrix_ub_12      0.0702
_diffrn_orient_matrix_ub_13      -0.024572
_diffrn_orient_matrix_ub_21      0.062125
_diffrn_orient_matrix_ub_22      0.000185
_diffrn_orient_matrix_ub_23      -0.00444
_diffrn_orient_matrix_ub_31      -0.020558
_diffrn_orient_matrix_ub_32      -0.028462
_diffrn_orient_matrix_ub_33      -0.060634
_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.079
_diffrn_reflns_av_unetI/netI     0.1284
_diffrn_reflns_number            17029
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.046
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.968
_reflns_Friedel_coverage         0
_reflns_number_total             7042
_reflns_number_gt                4212
_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_solution    'SHELXT-2014 (Sheldrick, 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_secondary   difmap
_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)+(0.0484P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7042
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1344
_refine_ls_R_factor_gt           0.059
_refine_ls_wR_factor_ref         0.1322
_refine_ls_wR_factor_gt          0.1072
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.346
_refine_diff_density_min         -1.996
_refine_diff_density_rms         0.199

#----------------------------------------------------------------------------#
#                   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'
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 0.7350(4) 0.4894(5) 0.6103(4) 0.0202(16) Uani 1 1 d . . . . .
C2 C 0.6894(4) 0.5437(4) 0.6545(4) 0.0182(16) Uani 1 1 d . . . . .
C3 C 0.6080(4) 0.5702(4) 0.4904(4) 0.0172(15) Uani 1 1 d . . . . .
C4 C 0.5502(4) 0.5994(4) 0.4141(4) 0.0159(15) Uani 1 1 d . . . . .
C5 C 0.4324(4) 0.6990(5) 0.2998(4) 0.0206(16) Uani 1 1 d . . . . .
C6 C 0.4739(4) 0.6448(5) 0.2531(4) 0.0202(16) Uani 1 1 d . . . . .
C7 C 0.8178(5) 0.2930(6) 0.6046(5) 0.049(3) Uani 1 1 d . . . . .
H7A H 0.7609 0.2664 0.6087 0.073 Uiso 1 1 calc R U . . .
H7B H 0.8646 0.2445 0.631 0.073 Uiso 1 1 calc R U . . .
H7C H 0.8157 0.3034 0.5429 0.073 Uiso 1 1 calc R U . . .
C8 C 0.6532(7) 0.6735(7) 0.7904(5) 0.074(4) Uani 1 1 d . . . . .
H8A H 0.6594 0.7247 0.7476 0.111 Uiso 1 1 calc R U . . .
H8B H 0.6755 0.7009 0.8498 0.111 Uiso 1 1 calc R U . . .
H8C H 0.5908 0.6555 0.7798 0.111 Uiso 1 1 calc R U . . .
C9 C 0.3062(4) 0.7457(5) 0.1502(4) 0.0246(17) Uani 1 1 d . . . . .
H9A H 0.2798 0.6776 0.1502 0.03 Uiso 1 1 calc R U . . .
H9B H 0.259 0.7922 0.1183 0.03 Uiso 1 1 calc R U . . .
C10 C 0.3779(5) 0.7406(5) 0.1023(5) 0.0315(19) Uani 1 1 d . . . . .
H10A H 0.4086 0.8068 0.1088 0.038 Uiso 1 1 calc R U . . .
H10B H 0.3494 0.7303 0.0391 0.038 Uiso 1 1 calc R U . . .
C11 C 0.8196(4) 0.0117(4) 0.6853(4) 0.0145(14) Uani 1 1 d . . . . .
C12 C 0.7557(4) 0.0124(4) 0.6093(4) 0.0202(15) Uani 1 1 d . . . . .
C13 C 0.8966(4) 0.0571(5) 0.5661(4) 0.0176(15) Uani 1 1 d . . . . .
C14 C 0.9499(4) 0.1017(5) 0.5242(4) 0.0166(15) Uani 1 1 d . . . . .
C15 C 1.0028(4) 0.2068(5) 0.4115(4) 0.0194(16) Uani 1 1 d . . . . .
C16 C 1.0658(4) 0.2159(5) 0.4875(4) 0.0226(17) Uani 1 1 d . . . . .
C17 C 0.6057(5) -0.1016(5) 0.5056(4) 0.0313(19) Uani 1 1 d . . . . .
H17A H 0.6174 -0.0712 0.4534 0.047 Uiso 1 1 calc R U . . .
H17B H 0.5434 -0.1209 0.4924 0.047 Uiso 1 1 calc R U . . .
H17C H 0.6428 -0.1618 0.5228 0.047 Uiso 1 1 calc R U . . .
C18 C 0.9175(5) -0.0229(8) 0.8705(5) 0.071(3) Uani 1 1 d . . . . .
H18A H 0.952 -0.0709 0.846 0.107 Uiso 1 1 calc R U . . .
H18B H 0.9167 -0.0452 0.9292 0.107 Uiso 1 1 calc R U . . .
H18C H 0.9445 0.0445 0.8742 0.107 Uiso 1 1 calc R U . . .
C19 C 1.1079(5) 0.2961(6) 0.3159(5) 0.039(2) Uani 1 1 d . . . . .
H19A H 1.1204 0.273 0.2611 0.047 Uiso 1 1 calc R U . . .
H19B H 1.1128 0.3709 0.3176 0.047 Uiso 1 1 calc R U . . .
C20 C 1.1788(4) 0.2539(5) 0.3924(4) 0.0264(18) Uani 1 1 d . . . . .
H20A H 1.2369 0.2796 0.3894 0.032 Uiso 1 1 calc R U . . .
H20B H 1.1796 0.1792 0.3873 0.032 Uiso 1 1 calc R U . . .
S1 S 0.69789(11) 0.48905(12) 0.49534(11) 0.0224(4) Uani 1 1 d . . . . .
S2 S 0.59696(11) 0.60985(13) 0.59216(10) 0.0228(4) Uani 1 1 d . . . . .
S3 S 0.46042(11) 0.67895(13) 0.41334(10) 0.0229(4) Uani 1 1 d . . . . .
S4 S 0.55556(12) 0.55943(13) 0.31039(10) 0.0254(4) Uani 1 1 d . . . . .
S5 S 0.34808(13) 0.78872(14) 0.26145(12) 0.0352(5) Uani 1 1 d . . . . .
S6 S 0.45836(13) 0.64300(16) 0.13935(11) 0.0392(6) Uani 1 1 d . . . . .
S7 S 0.92812(11) 0.02555(12) 0.67750(10) 0.0195(4) Uani 1 1 d . . . . .
S8 S 0.78589(11) 0.02700(13) 0.51209(11) 0.0215(4) Uani 1 1 d . . . . .
S9 S 0.91761(11) 0.12019(12) 0.41020(10) 0.0201(4) Uani 1 1 d . . . . .
S10 S 1.05854(11) 0.14102(13) 0.57575(10) 0.0204(4) Uani 1 1 d . . . . .
S11 S 0.99588(13) 0.26300(15) 0.31060(12) 0.0372(6) Uani 1 1 d . . . . .
S12 S 1.16298(13) 0.28686(15) 0.49722(12) 0.0356(5) Uani 1 1 d . . . . .
Se1 Se 0.84147(5) 0.41947(5) 0.66600(5) 0.0335(2) Uani 1 1 d . . . . .
Se2 Se 0.71980(5) 0.55466(6) 0.77834(4) 0.0304(2) Uani 1 1 d . . . . .
Se3 Se 0.79908(5) -0.01702(6) 0.79614(5) 0.0330(2) Uani 1 1 d . . . . .
Se4 Se 0.63306(5) -0.00350(6) 0.60142(5) 0.0306(2) 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 1.340(9) . ?
C1 S1 1.755(6) . ?
C1 Se1 1.907(6) . ?
C2 S2 1.753(6) . ?
C2 Se2 1.895(6) . ?
C3 C4 1.356(7) . ?
C3 S2 1.749(7) . ?
C3 S1 1.760(7) . ?
C4 S4 1.750(6) . ?
C4 S3 1.759(6) . ?
C5 C6 1.323(9) . ?
C5 S3 1.753(6) . ?
C5 S5 1.759(6) . ?
C6 S6 1.753(6) . ?
C6 S4 1.764(6) . ?
C7 Se1 1.917(7) . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 Se2 1.926(8) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 C10 1.524(10) . ?
C9 S5 1.798(6) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 S6 1.791(7) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C12 1.343(8) . ?
C11 S7 1.757(7) . ?
C11 Se3 1.909(6) . ?
C12 S8 1.743(7) . ?
C12 Se4 1.913(6) . ?
C13 C14 1.340(9) . ?
C13 S7 1.750(6) . ?
C13 S8 1.765(6) . ?
C14 S9 1.756(6) . ?
C14 S10 1.762(6) . ?
C15 C16 1.340(8) . ?
C15 S11 1.740(6) . ?
C15 S9 1.759(7) . ?
C16 S10 1.742(7) . ?
C16 S12 1.765(7) . ?
C17 Se4 1.953(6) . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 Se3 1.918(7) . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C19 C20 1.513(8) . ?
C19 S11 1.798(7) . ?
C19 H19A 0.99 . ?
C19 H19B 0.99 . ?
C20 S12 1.799(7) . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?

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 118.0(4) . . ?
C2 C1 Se1 123.1(5) . . ?
S1 C1 Se1 118.8(4) . . ?
C1 C2 S2 117.0(5) . . ?
C1 C2 Se2 124.2(4) . . ?
S2 C2 Se2 118.8(4) . . ?
C4 C3 S2 121.8(5) . . ?
C4 C3 S1 123.3(5) . . ?
S2 C3 S1 115.0(3) . . ?
C3 C4 S4 124.0(5) . . ?
C3 C4 S3 121.2(5) . . ?
S4 C4 S3 114.7(3) . . ?
C6 C5 S3 117.9(5) . . ?
C6 C5 S5 127.8(5) . . ?
S3 C5 S5 114.3(4) . . ?
C5 C6 S6 129.1(5) . . ?
C5 C6 S4 117.4(5) . . ?
S6 C6 S4 113.5(4) . . ?
Se1 C7 H7A 109.5 . . ?
Se1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
Se1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
Se2 C8 H8A 109.5 . . ?
Se2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
Se2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 S5 112.2(5) . . ?
C10 C9 H9A 109.2 . . ?
S5 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
S5 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 S6 115.0(5) . . ?
C9 C10 H10A 108.5 . . ?
S6 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
S6 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C12 C11 S7 116.2(5) . . ?
C12 C11 Se3 123.6(5) . . ?
S7 C11 Se3 119.8(3) . . ?
C11 C12 S8 118.4(5) . . ?
C11 C12 Se4 123.7(5) . . ?
S8 C12 Se4 117.9(3) . . ?
C14 C13 S7 124.1(5) . . ?
C14 C13 S8 121.9(5) . . ?
S7 C13 S8 114.0(4) . . ?
C13 C14 S9 121.8(5) . . ?
C13 C14 S10 124.1(5) . . ?
S9 C14 S10 114.1(4) . . ?
C16 C15 S11 129.3(5) . . ?
C16 C15 S9 116.4(5) . . ?
S11 C15 S9 114.2(3) . . ?
C15 C16 S10 118.4(5) . . ?
C15 C16 S12 122.6(5) . . ?
S10 C16 S12 118.4(3) . . ?
Se4 C17 H17A 109.5 . . ?
Se4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
Se4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Se3 C18 H18A 109.5 . . ?
Se3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
Se3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 S11 116.7(5) . . ?
C20 C19 H19A 108.1 . . ?
S11 C19 H19A 108.1 . . ?
C20 C19 H19B 108.1 . . ?
S11 C19 H19B 108.1 . . ?
H19A C19 H19B 107.3 . . ?
C19 C20 S12 113.2(5) . . ?
C19 C20 H20A 108.9 . . ?
S12 C20 H20A 108.9 . . ?
C19 C20 H20B 108.9 . . ?
S12 C20 H20B 108.9 . . ?
H20A C20 H20B 107.8 . . ?
C1 S1 C3 94.6(3) . . ?
C3 S2 C2 95.4(3) . . ?
C5 S3 C4 94.3(3) . . ?
C4 S4 C6 94.3(3) . . ?
C5 S5 C9 99.6(3) . . ?
C6 S6 C10 102.4(3) . . ?
C13 S7 C11 94.7(3) . . ?
C12 S8 C13 93.9(3) . . ?
C14 S9 C15 94.1(3) . . ?
C16 S10 C14 93.6(3) . . ?
C15 S11 C19 104.2(3) . . ?
C16 S12 C20 97.2(3) . . ?
C1 Se1 C7 99.3(3) . . ?
C2 Se2 C8 100.0(3) . . ?
C11 Se3 C18 101.1(3) . . ?
C12 Se4 C17 97.3(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
S1 C1 C2 S2 -0.3(7) . . . . ?
Se1 C1 C2 S2 175.9(3) . . . . ?
S1 C1 C2 Se2 -179.3(3) . . . . ?
Se1 C1 C2 Se2 -3.1(8) . . . . ?
S2 C3 C4 S4 -178.0(3) . . . . ?
S1 C3 C4 S4 1.0(8) . . . . ?
S2 C3 C4 S3 -0.1(8) . . . . ?
S1 C3 C4 S3 178.9(3) . . . . ?
S3 C5 C6 S6 177.2(4) . . . . ?
S5 C5 C6 S6 -0.8(11) . . . . ?
S3 C5 C6 S4 -1.5(8) . . . . ?
S5 C5 C6 S4 -179.4(4) . . . . ?
S5 C9 C10 S6 69.6(6) . . . . ?
S7 C11 C12 S8 -0.1(7) . . . . ?
Se3 C11 C12 S8 -173.5(3) . . . . ?
S7 C11 C12 Se4 179.1(3) . . . . ?
Se3 C11 C12 Se4 5.7(8) . . . . ?
S7 C13 C14 S9 173.7(3) . . . . ?
S8 C13 C14 S9 -7.5(8) . . . . ?
S7 C13 C14 S10 -3.1(9) . . . . ?
S8 C13 C14 S10 175.7(3) . . . . ?
S11 C15 C16 S10 -174.6(4) . . . . ?
S9 C15 C16 S10 1.0(8) . . . . ?
S11 C15 C16 S12 -3.7(10) . . . . ?
S9 C15 C16 S12 171.9(4) . . . . ?
S11 C19 C20 S12 -56.3(7) . . . . ?
C2 C1 S1 C3 0.4(6) . . . . ?
Se1 C1 S1 C3 -176.0(4) . . . . ?
C4 C3 S1 C1 -179.4(6) . . . . ?
S2 C3 S1 C1 -0.4(4) . . . . ?
C4 C3 S2 C2 179.3(5) . . . . ?
S1 C3 S2 C2 0.2(4) . . . . ?
C1 C2 S2 C3 0.0(6) . . . . ?
Se2 C2 S2 C3 179.0(4) . . . . ?
C6 C5 S3 C4 8.0(6) . . . . ?
S5 C5 S3 C4 -173.8(4) . . . . ?
C3 C4 S3 C5 170.2(6) . . . . ?
S4 C4 S3 C5 -11.7(4) . . . . ?
C3 C4 S4 C6 -170.8(6) . . . . ?
S3 C4 S4 C6 11.1(4) . . . . ?
C5 C6 S4 C4 -5.9(6) . . . . ?
S6 C6 S4 C4 175.2(4) . . . . ?
C6 C5 S5 C9 23.2(7) . . . . ?
S3 C5 S5 C9 -154.8(4) . . . . ?
C10 C9 S5 C5 -55.8(5) . . . . ?
C5 C6 S6 C10 4.4(8) . . . . ?
S4 C6 S6 C10 -176.9(4) . . . . ?
C9 C10 S6 C6 -38.8(6) . . . . ?
C14 C13 S7 C11 162.7(6) . . . . ?
S8 C13 S7 C11 -16.2(4) . . . . ?
C12 C11 S7 C13 10.0(5) . . . . ?
Se3 C11 S7 C13 -176.4(4) . . . . ?
C11 C12 S8 C13 -9.7(5) . . . . ?
Se4 C12 S8 C13 171.1(4) . . . . ?
C14 C13 S8 C12 -162.8(6) . . . . ?
S7 C13 S8 C12 16.1(4) . . . . ?
C13 C14 S9 C15 165.4(6) . . . . ?
S10 C14 S9 C15 -17.5(4) . . . . ?
C16 C15 S9 C14 10.1(6) . . . . ?
S11 C15 S9 C14 -173.6(4) . . . . ?
C15 C16 S10 C14 -11.4(6) . . . . ?
S12 C16 S10 C14 177.3(4) . . . . ?
C13 C14 S10 C16 -165.1(6) . . . . ?
S9 C14 S10 C16 17.9(4) . . . . ?
C16 C15 S11 C19 21.8(8) . . . . ?
S9 C15 S11 C19 -153.9(4) . . . . ?
C20 C19 S11 C15 10.4(7) . . . . ?
C15 C16 S12 C20 -37.5(6) . . . . ?
S10 C16 S12 C20 133.5(4) . . . . ?
C19 C20 S12 C16 66.9(5) . . . . ?
C1 C2 Se2 C8 161.9(6) . . . . ?
S2 C2 Se2 C8 -17.0(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 2190024'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University of Rennes 
France
;
_audit_update_record             
;
2022-10-05 deposited with the CCDC.	2022-10-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT341_shelx               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0162 Ang.
RESPONSE: The cristal is a twinned cristal of moderate quality this could explain this alert 
;
# Added during the CSD deposition process: Wednesday 05 October 2022 09:00 AM
# end Validation Reply Form


_audit_creation_date             2022-10-04T09:46:38-00:00
_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            'C10 H12 Br S4 Se2'
_chemical_formula_moiety         'C10 H12 S4 Se2, Br'
_chemical_formula_weight         498.27

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   6.9069(11)
_cell_length_b                   11.1580(15)
_cell_length_c                   19.166(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.399(6)
_cell_angle_gamma                90
_cell_volume                     1475.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3908
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      27.42
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    2.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             956

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

_exptl_absorpt_coefficient_mu    8.259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1
;
_exptl_absorpt_correction_T_min  0.616
_exptl_absorpt_correction_T_max  0.781

#----------------------------------------------------------------------------#
#                   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      0.096279
_diffrn_orient_matrix_ub_12      -0.048333
_diffrn_orient_matrix_ub_13      0.028449
_diffrn_orient_matrix_ub_21      -0.088538
_diffrn_orient_matrix_ub_22      0.000607
_diffrn_orient_matrix_ub_23      0.039968
_diffrn_orient_matrix_ub_31      -0.062372
_diffrn_orient_matrix_ub_32      -0.07547
_diffrn_orient_matrix_ub_33      -0.017898
_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  0.066
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_number            3568
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.112
_diffrn_reflns_theta_max         27.554
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.99
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.99
_reflns_Friedel_coverage         0
_reflns_number_total             3568
_reflns_number_gt                3277
_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_solution    'SHELXT-2014 (Sheldrick, 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_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+66.9018P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3568
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0682
_refine_ls_wR_factor_ref         0.1733
_refine_ls_wR_factor_gt          0.1703
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.359
_refine_diff_density_min         -1.951
_refine_diff_density_rms         0.29

#----------------------------------------------------------------------------#
#                   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'
Br Br -0.2901 2.4595 '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 0.243(2) 0.5211(11) 0.5183(6) 0.015(2) Uani 1 1 d . . . . .
C2 C 0.265(2) 0.4243(10) 0.3983(6) 0.013(2) Uani 1 1 d . . . . .
C3 C 0.267(2) 0.3301(10) 0.4458(6) 0.014(2) Uani 1 1 d . . . . .
C4 C 0.234(3) 0.5713(12) 0.2746(7) 0.029(3) Uani 1 1 d . . . . .
H4A H 0.1163 0.6037 0.2943 0.043 Uiso 1 1 calc R U . . .
H4B H 0.225 0.5789 0.2236 0.043 Uiso 1 1 calc R U . . .
H4C H 0.347 0.616 0.2931 0.043 Uiso 1 1 calc R U . . .
C5 C 0.247(3) 0.0976(11) 0.5098(6) 0.024(3) Uani 1 1 d . . . . .
H5A H 0.3679 0.107 0.538 0.036 Uiso 1 1 calc R U . . .
H5B H 0.2172 0.0122 0.5045 0.036 Uiso 1 1 calc R U . . .
H5C H 0.1415 0.1377 0.5331 0.036 Uiso 1 1 calc R U . . .
C6 C 0.246(2) 0.6065(9) 0.5722(6) 0.013(2) Uani 1 1 d . . . . .
C7 C 0.240(2) 0.7070(10) 0.6935(6) 0.015(2) Uani 1 1 d . . . . .
C8 C 0.223(2) 0.7972(11) 0.6463(6) 0.018(3) Uani 1 1 d . . . . .
C9 C 0.245(2) 0.7141(10) 0.7723(6) 0.018(2) Uani 1 1 d . . . . .
H9A H 0.2739 0.7966 0.787 0.027 Uiso 1 1 calc R U . . .
H9B H 0.3467 0.6605 0.7916 0.027 Uiso 1 1 calc R U . . .
H9C H 0.1197 0.6898 0.7895 0.027 Uiso 1 1 calc R U . . .
C10 C 0.229(2) 0.9293(11) 0.6616(6) 0.020(3) Uani 1 1 d . . . . .
H10A H 0.2599 0.942 0.7114 0.03 Uiso 1 1 calc R U . . .
H10B H 0.1019 0.9647 0.6493 0.03 Uiso 1 1 calc R U . . .
H10C H 0.3278 0.9674 0.6339 0.03 Uiso 1 1 calc R U . . .
Br1 Br 0.2432(3) 0.37439(11) 0.12655(6) 0.0236(3) Uani 1 1 d . . . . .
S1 S 0.2533(5) 0.5676(2) 0.43159(15) 0.0144(6) Uani 1 1 d . . . . .
S2 S 0.2680(6) 0.3708(2) 0.53223(15) 0.0160(6) Uani 1 1 d . . . . .
S3 S 0.2446(5) 0.5621(2) 0.65830(14) 0.0141(6) Uani 1 1 d . . . . .
S4 S 0.2299(5) 0.7581(2) 0.55858(14) 0.0143(6) Uani 1 1 d . . . . .
Se1 Se 0.2617(2) 0.40145(10) 0.30010(6) 0.0154(3) Uani 1 1 d . . . . .
Se2 Se 0.2770(2) 0.16863(10) 0.41869(6) 0.0142(3) 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 C6 1.406(16) . ?
C1 S2 1.706(12) . ?
C1 S1 1.745(12) . ?
C2 C3 1.390(16) . ?
C2 S1 1.724(11) . ?
C2 Se1 1.899(11) . ?
C3 S2 1.718(11) . ?
C3 Se2 1.877(11) . ?
C4 Se1 1.964(13) . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C5 Se2 1.937(12) . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 S4 1.715(11) . ?
C6 S3 1.723(11) . ?
C7 C8 1.354(16) . ?
C7 C9 1.512(15) . ?
C7 S3 1.753(11) . ?
C8 C10 1.503(16) . ?
C8 S4 1.740(12) . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 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
C6 C1 S2 123.6(9) . . ?
C6 C1 S1 119.9(9) . . ?
S2 C1 S1 115.7(7) . . ?
C3 C2 S1 117.3(8) . . ?
C3 C2 Se1 123.1(8) . . ?
S1 C2 Se1 119.5(6) . . ?
C2 C3 S2 115.5(8) . . ?
C2 C3 Se2 123.0(8) . . ?
S2 C3 Se2 121.4(7) . . ?
Se1 C4 H4A 109.5 . . ?
Se1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
Se1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Se2 C5 H5A 109.5 . . ?
Se2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
Se2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C6 S4 123.9(9) . . ?
C1 C6 S3 120.6(8) . . ?
S4 C6 S3 115.3(6) . . ?
C8 C7 C9 128.8(11) . . ?
C8 C7 S3 115.5(9) . . ?
C9 C7 S3 115.6(8) . . ?
C7 C8 C10 126.8(11) . . ?
C7 C8 S4 117.0(9) . . ?
C10 C8 S4 115.6(9) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 S1 C1 94.6(6) . . ?
C1 S2 C3 96.4(6) . . ?
C6 S3 C7 96.0(5) . . ?
C6 S4 C8 96.0(5) . . ?
C2 Se1 C4 96.5(5) . . ?
C3 Se2 C5 97.9(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
S1 C2 C3 S2 -2.7(15) . . . . ?
Se1 C2 C3 S2 -179.7(7) . . . . ?
S1 C2 C3 Se2 179.6(8) . . . . ?
Se1 C2 C3 Se2 2.5(18) . . . . ?
S2 C1 C6 S4 177.6(8) . . . . ?
S1 C1 C6 S4 8.4(18) . . . . ?
S2 C1 C6 S3 -8.6(18) . . . . ?
S1 C1 C6 S3 -177.8(8) . . . . ?
C9 C7 C8 C10 7(3) . . . . ?
S3 C7 C8 C10 -175.6(13) . . . . ?
C9 C7 C8 S4 177.7(12) . . . . ?
S3 C7 C8 S4 -5.2(18) . . . . ?
C3 C2 S1 C1 -1.4(13) . . . . ?
Se1 C2 S1 C1 175.7(8) . . . . ?
C6 C1 S1 C2 175.2(12) . . . . ?
S2 C1 S1 C2 5.1(10) . . . . ?
C6 C1 S2 C3 -176.0(13) . . . . ?
S1 C1 S2 C3 -6.3(10) . . . . ?
C2 C3 S2 C1 5.3(12) . . . . ?
Se2 C3 S2 C1 -176.8(9) . . . . ?
C1 C6 S3 C7 -177.6(12) . . . . ?
S4 C6 S3 C7 -3.3(9) . . . . ?
C8 C7 S3 C6 5.0(14) . . . . ?
C9 C7 S3 C6 -177.4(12) . . . . ?
C1 C6 S4 C8 175.2(13) . . . . ?
S3 C6 S4 C8 1.1(10) . . . . ?
C7 C8 S4 C6 2.5(14) . . . . ?
C10 C8 S4 C6 174.0(12) . . . . ?
C3 C2 Se1 C4 174.8(12) . . . . ?
S1 C2 Se1 C4 -2.2(10) . . . . ?
C2 C3 Se2 C5 -174.2(13) . . . . ?
S2 C3 Se2 C5 8.1(11) . . . . ?

####################################################################### 
# 
# 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 2190022'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University of Rennes 
France
;
_audit_update_record             
;
2022-10-05 deposited with the CCDC.	2022-10-07 downloaded from the CCDC.
;

_audit_creation_date             2022-09-16T08:41:30-00:00
_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            'C10 H12 S4 Se2'
_chemical_formula_moiety         'C10 H12 S4 Se2'
_chemical_formula_weight         418.36

#----------------------------------------------------------------------------#
#                   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                   16.179(9)
_cell_length_b                   8.230(5)
_cell_length_c                   11.342(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.59(3)
_cell_angle_gamma                90
_cell_volume                     1500.2(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3025
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      26.78
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.852
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816

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

_exptl_absorpt_coefficient_mu    5.458
_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  0.279
_exptl_absorpt_correction_T_max  0.897

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.4582  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
# Ratio of Min/Max transmission:               0.6145                          #
#------------------------------------------------------------------------------# 

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

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      -0.085089
_diffrn_orient_matrix_ub_12      -0.011264
_diffrn_orient_matrix_ub_13      0.00978
_diffrn_orient_matrix_ub_21      -0.02457
_diffrn_orient_matrix_ub_22      0.0105
_diffrn_orient_matrix_ub_23      -0.061128
_diffrn_orient_matrix_ub_31      0.005812
_diffrn_orient_matrix_ub_32      -0.120523
_diffrn_orient_matrix_ub_33      -0.00624
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_number            10468
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.781
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.984
_reflns_Friedel_coverage         0
_reflns_number_total             3410
_reflns_number_gt                2161
_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_solution    'SHELXT-2014 (Sheldrick, 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_secondary   difmap
_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)+(0.0574P)²+11.1312P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3410
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1271
_refine_ls_R_factor_gt           0.0736
_refine_ls_wR_factor_ref         0.1854
_refine_ls_wR_factor_gt          0.1559
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.369
_refine_diff_density_min         -1.429
_refine_diff_density_rms         0.144

#----------------------------------------------------------------------------#
#                   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'
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 0.3248(5) 0.3775(9) 0.3170(7) 0.0371(17) Uani 1 1 d . . . . .
C2 C 0.1740(4) 0.4112(10) 0.3556(7) 0.0384(18) Uani 1 1 d . . . . .
C3 C 0.1838(5) 0.5186(10) 0.2722(7) 0.0420(19) Uani 1 1 d . . . . .
C4 C 0.1042(9) 0.264(2) 0.5561(15) 0.139(7) Uani 1 1 d . . . . .
H4A H 0.1147 0.1568 0.5275 0.208 Uiso 1 1 calc R U . . .
H4B H 0.06 0.2589 0.6057 0.208 Uiso 1 1 calc R U . . .
H4C H 0.1536 0.3048 0.6012 0.208 Uiso 1 1 calc R U . . .
C5 C 0.1363(9) 0.8522(15) 0.3060(15) 0.116(5) Uani 1 1 d . . . . .
H5A H 0.1548 0.8161 0.3851 0.174 Uiso 1 1 calc R U . . .
H5B H 0.0907 0.9264 0.3079 0.174 Uiso 1 1 calc R U . . .
H5C H 0.1812 0.906 0.2735 0.174 Uiso 1 1 calc R U . . .
C6 C 0.4080(5) 0.3610(9) 0.3442(6) 0.0357(17) Uani 1 1 d . . . . .
C7 C 0.5676(5) 0.4065(9) 0.3651(7) 0.0356(17) Uani 1 1 d . . . . .
C8 C 0.5572(4) 0.2993(9) 0.4490(7) 0.0347(17) Uani 1 1 d . . . . .
C9 C 0.6481(5) 0.4805(10) 0.3412(8) 0.046(2) Uani 1 1 d . . . . .
H9A H 0.6477 0.5945 0.359 0.069 Uiso 1 1 calc R U . . .
H9B H 0.6555 0.4657 0.2591 0.069 Uiso 1 1 calc R U . . .
H9C H 0.693 0.4291 0.39 0.069 Uiso 1 1 calc R U . . .
C10 C 0.6208(5) 0.2251(11) 0.5373(7) 0.047(2) Uani 1 1 d . . . . .
H10A H 0.6747 0.2679 0.5266 0.07 Uiso 1 1 calc R U . . .
H10B H 0.6209 0.1094 0.5265 0.07 Uiso 1 1 calc R U . . .
H10C H 0.6081 0.25 0.6159 0.07 Uiso 1 1 calc R U . . .
S1 S 0.25311(12) 0.2683(3) 0.39147(19) 0.0439(5) Uani 1 1 d . . . . .
S2 S 0.27757(13) 0.5090(3) 0.20741(19) 0.0477(5) Uani 1 1 d . . . . .
S3 S 0.47949(12) 0.4677(3) 0.26932(17) 0.0407(5) Uani 1 1 d . . . . .
S4 S 0.45366(12) 0.2310(2) 0.45519(18) 0.0390(5) Uani 1 1 d . . . . .
Se1 Se 0.07349(6) 0.40109(15) 0.42777(10) 0.0662(4) Uani 1 1 d . . . . .
Se2 Se 0.10064(7) 0.66795(14) 0.20858(10) 0.0682(4) 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 C6 1.352(11) . ?
C1 S2 1.756(8) . ?
C1 S1 1.759(8) . ?
C2 C3 1.317(11) . ?
C2 S1 1.752(8) . ?
C2 Se1 1.904(7) . ?
C3 S2 1.761(8) . ?
C3 Se2 1.903(8) . ?
C4 Se1 1.865(14) . ?
C4 H4A 0.96 . ?
C4 H4B 0.96 . ?
C4 H4C 0.96 . ?
C5 Se2 1.925(13) . ?
C5 H5A 0.96 . ?
C5 H5B 0.96 . ?
C5 H5C 0.96 . ?
C6 S3 1.749(7) . ?
C6 S4 1.749(8) . ?
C7 C8 1.322(10) . ?
C7 C9 1.491(10) . ?
C7 S3 1.764(8) . ?
C8 C10 1.483(11) . ?
C8 S4 1.775(7) . ?
C9 H9A 0.96 . ?
C9 H9B 0.96 . ?
C9 H9C 0.96 . ?
C10 H10A 0.96 . ?
C10 H10B 0.96 . ?
C10 H10C 0.96 . ?

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
C6 C1 S2 124.4(6) . . ?
C6 C1 S1 122.2(6) . . ?
S2 C1 S1 113.4(4) . . ?
C3 C2 S1 118.1(6) . . ?
C3 C2 Se1 121.2(6) . . ?
S1 C2 Se1 120.5(5) . . ?
C2 C3 S2 116.8(6) . . ?
C2 C3 Se2 124.5(6) . . ?
S2 C3 Se2 118.4(5) . . ?
Se1 C4 H4A 109.5 . . ?
Se1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
Se1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Se2 C5 H5A 109.5 . . ?
Se2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
Se2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C6 S3 122.3(6) . . ?
C1 C6 S4 123.6(6) . . ?
S3 C6 S4 114.1(4) . . ?
C8 C7 C9 126.2(7) . . ?
C8 C7 S3 118.2(6) . . ?
C9 C7 S3 115.6(6) . . ?
C7 C8 C10 128.6(7) . . ?
C7 C8 S4 116.0(6) . . ?
C10 C8 S4 115.4(6) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 S1 C1 92.9(4) . . ?
C1 S2 C3 93.3(4) . . ?
C6 S3 C7 95.2(4) . . ?
C6 S4 C8 95.8(4) . . ?
C4 Se1 C2 101.4(4) . . ?
C3 Se2 C5 98.0(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
S1 C2 C3 S2 -1.3(9) . . . . ?
Se1 C2 C3 S2 -177.0(4) . . . . ?
S1 C2 C3 Se2 172.9(4) . . . . ?
Se1 C2 C3 Se2 -2.8(10) . . . . ?
S2 C1 C6 S3 -1.5(10) . . . . ?
S1 C1 C6 S3 179.3(4) . . . . ?
S2 C1 C6 S4 179.1(4) . . . . ?
S1 C1 C6 S4 0.0(10) . . . . ?
C9 C7 C8 C10 -1.0(13) . . . . ?
S3 C7 C8 C10 177.8(6) . . . . ?
C9 C7 C8 S4 -179.4(6) . . . . ?
S3 C7 C8 S4 -0.5(8) . . . . ?
C3 C2 S1 C1 14.6(7) . . . . ?
Se1 C2 S1 C1 -169.7(5) . . . . ?
C6 C1 S1 C2 156.5(7) . . . . ?
S2 C1 S1 C2 -22.7(5) . . . . ?
C6 C1 S2 C3 -157.0(7) . . . . ?
S1 C1 S2 C3 22.3(5) . . . . ?
C2 C3 S2 C1 -12.8(7) . . . . ?
Se2 C3 S2 C1 172.7(5) . . . . ?
C1 C6 S3 C7 172.2(7) . . . . ?
S4 C6 S3 C7 -8.4(5) . . . . ?
C8 C7 S3 C6 5.4(6) . . . . ?
C9 C7 S3 C6 -175.6(6) . . . . ?
C1 C6 S4 C8 -172.4(7) . . . . ?
S3 C6 S4 C8 8.2(5) . . . . ?
C7 C8 S4 C6 -4.7(6) . . . . ?
C10 C8 S4 C6 176.7(6) . . . . ?

####################################################################### 
# 
# 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 2190023'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University of Rennes 
France
;
_audit_update_record             
;
2022-10-05 deposited with the CCDC.	2022-10-07 downloaded from the CCDC.
;

_audit_creation_date             2022-10-03T13:43:29-00:00
_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 H20 Br2 S12 Se4'
_chemical_formula_moiety         'C10 H10 S6 Se2, Br'
_chemical_formula_weight         1120.74

#----------------------------------------------------------------------------#
#                   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                   5.8409(4)
_cell_length_b                   17.6599(12)
_cell_length_c                   16.2327(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.323(2)
_cell_angle_gamma                90
_cell_volume                     1671.58(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9966
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      26.64
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    2.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1076

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

_exptl_absorpt_coefficient_mu    7.546
_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  0.703
_exptl_absorpt_correction_T_max  0.797


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

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      0.128582
_diffrn_orient_matrix_ub_12      0.036128
_diffrn_orient_matrix_ub_13      0.013488
_diffrn_orient_matrix_ub_21      0.112338
_diffrn_orient_matrix_ub_22      -0.042648
_diffrn_orient_matrix_ub_23      -0.001387
_diffrn_orient_matrix_ub_31      0.01603
_diffrn_orient_matrix_ub_32      0.009077
_diffrn_orient_matrix_ub_33      -0.0602
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_number            40223
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.766
_diffrn_reflns_theta_max         27.546
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_coverage         0
_reflns_number_total             3849
_reflns_number_gt                2962
_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_solution    'SHELXT-2014 (Sheldrick, 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_secondary   difmap
_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)+(0.0372P)²+2.3719P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3849
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0854
_refine_ls_wR_factor_gt          0.0759
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.131

#----------------------------------------------------------------------------#
#                   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'
Br Br -0.2901 2.4595 '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 0.1380(6) 0.5133(2) 0.2328(2) 0.0337(8) Uani 1 1 d . . . . .
C2 C -0.1881(6) 0.5783(2) 0.3053(2) 0.0315(8) Uani 1 1 d . . . . .
C3 C -0.1935(6) 0.6088(2) 0.2276(2) 0.0322(8) Uani 1 1 d . . . . .
C4 C -0.2591(7) 0.5566(3) 0.4792(2) 0.0463(11) Uani 1 1 d . . . . .
H4A H -0.2558 0.5031 0.4691 0.069 Uiso 1 1 calc R U . . .
H4B H -0.3461 0.5666 0.5264 0.069 Uiso 1 1 calc R U . . .
H4C H -0.1053 0.5749 0.4894 0.069 Uiso 1 1 calc R U . . .
C5 C -0.2871(9) 0.7042(3) 0.0853(3) 0.0644(15) Uani 1 1 d . . . . .
H5A H -0.1344 0.7238 0.0942 0.097 Uiso 1 1 calc R U . . .
H5B H -0.3819 0.7412 0.0565 0.097 Uiso 1 1 calc R U . . .
H5C H -0.2833 0.6588 0.0529 0.097 Uiso 1 1 calc R U . . .
C6 C 0.3232(6) 0.4690(2) 0.2136(2) 0.0321(8) Uani 1 1 d . . . . .
C7 C 0.6519(6) 0.4060(2) 0.1407(2) 0.0311(8) Uani 1 1 d . . . . .
C8 C 0.6632(6) 0.3766(2) 0.2177(2) 0.0293(8) Uani 1 1 d . . . . .
C9 C 0.9938(8) 0.3078(3) 0.0924(3) 0.0490(11) Uani 1 1 d . . . . .
H9A H 1.0174 0.2764 0.0446 0.059 Uiso 1 1 calc R U . . .
H9B H 1.1432 0.3246 0.1144 0.059 Uiso 1 1 calc R U . . .
C10 C 0.8863(8) 0.2604(2) 0.1564(3) 0.0457(10) Uani 1 1 d . . . . .
H10A H 0.9776 0.2151 0.1658 0.055 Uiso 1 1 calc R U . . .
H10B H 0.735 0.2449 0.1351 0.055 Uiso 1 1 calc R U . . .
S1 S 0.02058(17) 0.51082(6) 0.32813(6) 0.0368(2) Uani 1 1 d . . . . .
S2 S 0.00847(17) 0.57541(6) 0.16310(6) 0.0375(2) Uani 1 1 d . . . . .
S3 S 0.43274(17) 0.47075(6) 0.11704(6) 0.0368(2) Uani 1 1 d . . . . .
S4 S 0.45856(16) 0.40809(6) 0.28406(6) 0.0350(2) Uani 1 1 d . . . . .
S5 S 0.8277(2) 0.38968(8) 0.05947(7) 0.0524(3) Uani 1 1 d . . . . .
S6 S 0.85977(17) 0.30796(6) 0.25383(6) 0.0382(2) Uani 1 1 d . . . . .
Se1 Se -0.40017(6) 0.60752(2) 0.38376(2) 0.03907(12) Uani 1 1 d . . . . .
Se2 Se -0.41158(7) 0.68177(3) 0.19063(3) 0.04450(13) Uani 1 1 d . . . . .
Br1 Br 0.74466(8) 0.33659(3) 0.45750(3) 0.05074(14) 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 C6 1.386(5) . ?
C1 S2 1.719(4) . ?
C1 S1 1.729(4) . ?
C2 C3 1.371(5) . ?
C2 S1 1.730(4) . ?
C2 Se1 1.898(4) . ?
C3 S2 1.725(4) . ?
C3 Se2 1.886(4) . ?
C4 Se1 1.933(4) . ?
C4 H4A 0.96 . ?
C4 H4B 0.96 . ?
C4 H4C 0.96 . ?
C5 Se2 1.938(5) . ?
C5 H5A 0.96 . ?
C5 H5B 0.96 . ?
C5 H5C 0.96 . ?
C6 S4 1.727(4) . ?
C6 S3 1.728(4) . ?
C7 C8 1.351(5) . ?
C7 S5 1.742(4) . ?
C7 S3 1.743(4) . ?
C8 S4 1.746(4) . ?
C8 S6 1.747(4) . ?
C9 C10 1.499(6) . ?
C9 S5 1.805(5) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 S6 1.805(4) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?

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
C6 C1 S2 122.2(3) . . ?
C6 C1 S1 122.8(3) . . ?
S2 C1 S1 115.0(2) . . ?
C3 C2 S1 116.5(3) . . ?
C3 C2 Se1 122.0(3) . . ?
S1 C2 Se1 121.5(2) . . ?
C2 C3 S2 116.4(3) . . ?
C2 C3 Se2 122.7(3) . . ?
S2 C3 Se2 120.9(2) . . ?
Se1 C4 H4A 109.5 . . ?
Se1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
Se1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Se2 C5 H5A 109.5 . . ?
Se2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
Se2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C6 S4 122.5(3) . . ?
C1 C6 S3 121.9(3) . . ?
S4 C6 S3 115.6(2) . . ?
C8 C7 S5 129.6(3) . . ?
C8 C7 S3 116.9(3) . . ?
S5 C7 S3 113.5(2) . . ?
C7 C8 S4 116.7(3) . . ?
C7 C8 S6 124.9(3) . . ?
S4 C8 S6 118.3(2) . . ?
C10 C9 S5 114.4(3) . . ?
C10 C9 H9A 108.7 . . ?
S5 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
S5 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 S6 114.1(3) . . ?
C9 C10 H10A 108.7 . . ?
S6 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
S6 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C1 S1 C2 95.86(18) . . ?
C1 S2 C3 96.25(18) . . ?
C6 S3 C7 95.36(17) . . ?
C6 S4 C8 95.37(17) . . ?
C7 S5 C9 103.8(2) . . ?
C8 S6 C10 96.69(19) . . ?
C2 Se1 C4 98.42(17) . . ?
C3 Se2 C5 98.03(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C2 C3 S2 0.1(4) . . . . ?
Se1 C2 C3 S2 -179.17(19) . . . . ?
S1 C2 C3 Se2 178.89(19) . . . . ?
Se1 C2 C3 Se2 -0.4(5) . . . . ?
S2 C1 C6 S4 178.4(2) . . . . ?
S1 C1 C6 S4 -1.4(5) . . . . ?
S2 C1 C6 S3 -1.9(5) . . . . ?
S1 C1 C6 S3 178.3(2) . . . . ?
S5 C7 C8 S4 178.6(2) . . . . ?
S3 C7 C8 S4 -0.7(4) . . . . ?
S5 C7 C8 S6 -3.5(6) . . . . ?
S3 C7 C8 S6 177.1(2) . . . . ?
S5 C9 C10 S6 -64.8(4) . . . . ?
C6 C1 S1 C2 179.5(3) . . . . ?
S2 C1 S1 C2 -0.3(3) . . . . ?
C3 C2 S1 C1 0.1(3) . . . . ?
Se1 C2 S1 C1 179.4(2) . . . . ?
C6 C1 S2 C3 -179.5(3) . . . . ?
S1 C1 S2 C3 0.3(3) . . . . ?
C2 C3 S2 C1 -0.3(3) . . . . ?
Se2 C3 S2 C1 -179.1(2) . . . . ?
C1 C6 S3 C7 178.7(3) . . . . ?
S4 C6 S3 C7 -1.6(3) . . . . ?
C8 C7 S3 C6 1.4(3) . . . . ?
S5 C7 S3 C6 -178.1(2) . . . . ?
C1 C6 S4 C8 -179.0(3) . . . . ?
S3 C6 S4 C8 1.3(3) . . . . ?
C7 C8 S4 C6 -0.4(3) . . . . ?
S6 C8 S4 C6 -178.3(2) . . . . ?
C8 C7 S5 C9 12.6(4) . . . . ?
S3 C7 S5 C9 -168.1(2) . . . . ?
C10 C9 S5 C7 22.1(4) . . . . ?
C7 C8 S6 C10 -31.2(4) . . . . ?
S4 C8 S6 C10 146.6(2) . . . . ?
C9 C10 S6 C8 65.7(3) . . . . ?
C3 C2 Se1 C4 -170.9(3) . . . . ?
S1 C2 Se1 C4 9.8(3) . . . . ?
C2 C3 Se2 C5 173.5(3) . . . . ?
S2 C3 Se2 C5 -7.8(3) . . . . ?

