# 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 2020

####################################################################### 
# 
# 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 2040289'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;Universite Rennes
France
;
_audit_update_record             
;
2020-11-17 deposited with the CCDC.	2020-11-24 downloaded from the CCDC.
;

_audit_creation_date             2020-11-17T10:36:36-00:00
_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_moiety         'C12  H12  N2  Se2'
_chemical_formula_sum            'C12 H12 N2 Se2'
_chemical_formula_weight         342.16

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

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

_cell_length_a                   7.5686(4)
_cell_length_b                   21.7486(11)
_cell_length_c                   8.2075(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.783(2)
_cell_angle_gamma                90
_cell_volume                     1300.07(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9981
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      27.49
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664

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

_exptl_absorpt_coefficient_mu    5.663
_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  0.447
_exptl_absorpt_correction_T_max  0.753

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.3987  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------#


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

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      0.086963
_diffrn_orient_matrix_ub_12      -0.031777
_diffrn_orient_matrix_ub_13      -0.020606
_diffrn_orient_matrix_ub_21      -0.099284
_diffrn_orient_matrix_ub_22      -0.016936
_diffrn_orient_matrix_ub_23      -0.096099
_diffrn_orient_matrix_ub_31      0.037842
_diffrn_orient_matrix_ub_32      0.028593
_diffrn_orient_matrix_ub_33      -0.07982
_diffrn_measurement_device_type  'D8 VENTURE 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  0.0572
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_number            20013
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.579
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             2993
_reflns_number_gt                2631
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_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_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)+(0.0235P)²+1.4716P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2993
_refine_ls_number_parameters     185
_refine_ls_number_restraints     59
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.027
_refine_ls_wR_factor_ref         0.066
_refine_ls_wR_factor_gt          0.0637
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.5
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.086

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


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5385(3) 0.13114(10) 0.1889(3) 0.0170(4) Uani 1 1 d . . . . .
C2 C 0.4276(3) 0.13235(10) 0.0196(3) 0.0174(4) Uani 1 1 d . . . . .
C3 C 0.4905(3) 0.16378(12) -0.1020(3) 0.0228(5) Uani 1 1 d . . . . .
H3 H 0.417 0.1643 -0.2161 0.027 Uiso 1 1 calc R U . . .
C4 C 0.6571(4) 0.19419(12) -0.0608(3) 0.0253(5) Uani 1 1 d . . . . .
H4 H 0.6972 0.2153 -0.1456 0.03 Uiso 1 1 calc R U . . .
C5 C 0.7655(4) 0.19362(13) 0.1057(3) 0.0264(5) Uani 1 1 d . . . . .
H5 H 0.8801 0.2145 0.1356 0.032 Uiso 1 1 calc R U . . .
C6 C 0.7054(3) 0.16246(11) 0.2275(3) 0.0218(5) Uani 1 1 d . . . . .
H6 H 0.7803 0.1624 0.3411 0.026 Uiso 1 1 calc R U . . .
C7 C 0.4773(3) 0.09876(10) 0.3269(3) 0.0177(4) Uani 1 1 d . . . . .
H7 H 0.4207 0.0589 0.2784 0.021 Uiso 1 1 calc R U . . .
C8 C 0.6271(4) 0.08339(12) 0.4877(3) 0.0273(5) Uani 1 1 d . . . . .
H8A H 0.7214 0.058 0.4589 0.041 Uiso 1 1 calc R U . . .
H8B H 0.5734 0.0607 0.5658 0.041 Uiso 1 1 calc R U . . .
H8C H 0.6828 0.1215 0.5417 0.041 Uiso 1 1 calc R U . . .
C9 C 0.4333(3) 0.21375(11) 0.4674(3) 0.0182(5) Uani 1 1 d . . . . .
N1 N 0.5323(3) 0.25353(10) 0.5188(3) 0.0260(5) Uani 1 1 d . . . . .
Se1 Se 0.27946(3) 0.14792(2) 0.38751(3) 0.01758(8) Uani 1 1 d . . . . .
Se2A Se 0.2957(3) 0.02175(17) -0.1317(9) 0.0441(8) Uani 0.598(15) 1 d D U P A 1
C10A C 0.2429(3) 0.10051(11) -0.0352(3) 0.0200(4) Uani 0.598(15) 1 d D U P A 1
H10A H 0.2032 0.0912 0.0688 0.024 Uiso 0.598(15) 1 calc R U P A 1
C11A C 0.0886(9) 0.1365(3) -0.1566(9) 0.0147(10) Uani 0.598(15) 1 d D U P A 1
H11A H 0.0729 0.1762 -0.1059 0.022 Uiso 0.598(15) 1 calc R U P A 1
H11B H -0.026 0.113 -0.1783 0.022 Uiso 0.598(15) 1 calc R U P A 1
H11C H 0.1199 0.1433 -0.2635 0.022 Uiso 0.598(15) 1 calc R U P A 1
C12A C 0.065(3) -0.0109(14) -0.212(5) 0.026(3) Uani 0.598(15) 1 d D U P A 1
N2A N -0.075(3) -0.0329(12) -0.260(3) 0.037(4) Uani 0.598(15) 1 d D U P A 1
Se2B Se 0.2923(5) 0.0330(2) -0.1873(8) 0.0361(6) Uani 0.402(15) 1 d D U P A 2
C10B C 0.2429(3) 0.10051(11) -0.0352(3) 0.0200(4) Uani 0.402(15) 1 d D U P A 2
H10B H 0.2249 0.0797 0.0678 0.024 Uiso 0.402(15) 1 calc R U P A 2
C11B C 0.0766(14) 0.1337(5) -0.1097(14) 0.0163(13) Uani 0.402(15) 1 d D U P A 2
H11D H 0.0604 0.166 -0.0318 0.025 Uiso 0.402(15) 1 calc R U P A 2
H11E H -0.028 0.1054 -0.1319 0.025 Uiso 0.402(15) 1 calc R U P A 2
H11F H 0.0839 0.1524 -0.2164 0.025 Uiso 0.402(15) 1 calc R U P A 2
C12B C 0.061(4) -0.001(2) -0.234(7) 0.024(4) Uani 0.402(15) 1 d D U P A 2
N2B N -0.081(4) -0.0231(18) -0.273(5) 0.032(4) Uani 0.402(15) 1 d D U P A 2



#----------------------------------------------------------------------------#
#                   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 1.394(3) . ?
C1 C2 1.415(3) . ?
C1 C7 1.509(3) . ?
C2 C3 1.396(3) . ?
C2 C10B 1.515(3) . ?
C2 C10A 1.515(3) . ?
C3 C4 1.382(4) . ?
C3 H3 0.95 . ?
C4 C5 1.389(4) . ?
C4 H4 0.95 . ?
C5 C6 1.383(4) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 C8 1.525(3) . ?
C7 Se1 2.010(2) . ?
C7 H7 1 . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 N1 1.147(3) . ?
C9 Se1 1.849(2) . ?
Se2A C12A 1.833(17) . ?
Se2A C10A 1.974(3) . ?
C10A C11A 1.528(6) . ?
C10A H10A 1 . ?
C11A H11A 0.98 . ?
C11A H11B 0.98 . ?
C11A H11C 0.98 . ?
C12A N2A 1.129(19) . ?
Se2B C12B 1.84(3) . ?
Se2B C10B 2.027(4) . ?
C10B C11B 1.436(10) . ?
C10B H10B 1 . ?
C11B H11D 0.98 . ?
C11B H11E 0.98 . ?
C11B H11F 0.98 . ?
C12B N2B 1.14(3) . ?

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 C2 118.3(2) . . ?
C6 C1 C7 120.1(2) . . ?
C2 C1 C7 121.6(2) . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 C10B 118.6(2) . . ?
C1 C2 C10B 122.4(2) . . ?
C3 C2 C10A 118.6(2) . . ?
C1 C2 C10A 122.4(2) . . ?
C4 C3 C2 121.7(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 119.5(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 122.1(2) . . ?
C5 C6 H6 119 . . ?
C1 C6 H6 119 . . ?
C1 C7 C8 116.4(2) . . ?
C1 C7 Se1 109.81(15) . . ?
C8 C7 Se1 109.33(16) . . ?
C1 C7 H7 107 . . ?
C8 C7 H7 107 . . ?
Se1 C7 H7 107 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 Se1 178.2(2) . . ?
C9 Se1 C7 93.45(10) . . ?
C12A Se2A C10A 101.7(13) . . ?
C2 C10A C11A 116.1(3) . . ?
C2 C10A Se2A 104.15(17) . . ?
C11A C10A Se2A 112.6(3) . . ?
C2 C10A H10A 107.9 . . ?
C11A C10A H10A 107.9 . . ?
Se2A C10A H10A 107.9 . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
N2A C12A Se2A 178(3) . . ?
C12B Se2B C10B 95(2) . . ?
C11B C10B C2 121.9(5) . . ?
C11B C10B Se2B 112.9(4) . . ?
C2 C10B Se2B 101.78(17) . . ?
C11B C10B H10B 106.4 . . ?
C2 C10B H10B 106.4 . . ?
Se2B C10B H10B 106.4 . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
N2B C12B Se2B 176(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.1(3) . . . . ?
C7 C1 C2 C3 179.1(2) . . . . ?
C6 C1 C2 C10B -179.2(2) . . . . ?
C7 C1 C2 C10B -1.2(3) . . . . ?
C6 C1 C2 C10A -179.2(2) . . . . ?
C7 C1 C2 C10A -1.2(3) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C10B C2 C3 C4 179.6(2) . . . . ?
C10A C2 C3 C4 179.6(2) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C2 C1 C6 C5 -0.8(4) . . . . ?
C7 C1 C6 C5 -178.9(2) . . . . ?
C6 C1 C7 C8 -20.3(3) . . . . ?
C2 C1 C7 C8 161.7(2) . . . . ?
C6 C1 C7 Se1 104.5(2) . . . . ?
C2 C1 C7 Se1 -73.5(2) . . . . ?
C3 C2 C10A C11A -42.8(4) . . . . ?
C1 C2 C10A C11A 137.4(4) . . . . ?
C3 C2 C10A Se2A 81.6(3) . . . . ?
C1 C2 C10A Se2A -98.2(3) . . . . ?
C3 C2 C10B C11B -59.9(6) . . . . ?
C1 C2 C10B C11B 120.3(6) . . . . ?
C3 C2 C10B Se2B 66.8(3) . . . . ?
C1 C2 C10B Se2B -113.0(3) . . . . ?

####################################################################### 
# 
# 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_anti-bipy
_database_code_depnum_ccdc_archive 'CCDC 2040292'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2020-10-23 deposited with the CCDC.	2020-11-24 downloaded from the CCDC.
;

_audit_creation_date             2019-04-02T10:16:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_sum            'C17 H16 N3 Se2'
_chemical_formula_moiety         'C12 H12 N2 Se2, 0.5(C10 H8 N2)'
_chemical_formula_weight         420.25

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

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

_cell_length_a                   7.1221(4)
_cell_length_b                   28.6165(13)
_cell_length_c                   8.6600(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.763(2)
_cell_angle_gamma                90
_cell_volume                     1698.62(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4127
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      25.58
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             828

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

_exptl_absorpt_coefficient_mu    4.353
_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  0.347
_exptl_absorpt_correction_T_max  0.457

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.4930  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   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      0.09031
_diffrn_orient_matrix_ub_12      0.021215
_diffrn_orient_matrix_ub_13      -0.037359
_diffrn_orient_matrix_ub_21      0.086862
_diffrn_orient_matrix_ub_22      0.001783
_diffrn_orient_matrix_ub_23      0.111996
_diffrn_orient_matrix_ub_31      0.074729
_diffrn_orient_matrix_ub_32      -0.027711
_diffrn_orient_matrix_ub_33      -0.021395
_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  0.0291
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_number            12513
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.828
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             3912
_reflns_number_gt                3041
_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    'SIR-2014 (Burla et al., 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     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_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)+(0.0253P)²+0.9563P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3912
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0717
_refine_ls_wR_factor_gt          0.067
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.642
_refine_diff_density_rms         0.071

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


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1125(4) 0.15984(9) 0.9420(3) 0.0306(6) Uani 1 1 d . . . . .
C2 C -0.2369(4) 0.16400(8) 0.7866(3) 0.0285(6) Uani 1 1 d . . . . .
C3 C -0.4069(4) 0.19026(10) 0.7634(4) 0.0390(7) Uani 1 1 d . . . . .
H3 H -0.4907 0.1929 0.6606 0.047 Uiso 1 1 calc R U . . .
C4 C -0.4536(5) 0.21245(11) 0.8892(4) 0.0482(8) Uani 1 1 d . . . . .
H4 H -0.5676 0.2299 0.871 0.058 Uiso 1 1 calc R U . . .
C5 C -0.3323(5) 0.20870(11) 1.0403(4) 0.0497(8) Uani 1 1 d . . . . .
H5 H -0.3628 0.2237 1.1256 0.06 Uiso 1 1 calc R U . . .
C6 C -0.1637(5) 0.18249(10) 1.0664(4) 0.0415(7) Uani 1 1 d . . . . .
H6 H -0.0824 0.1799 1.1701 0.05 Uiso 1 1 calc R U . . .
C7 C 0.0740(4) 0.13227(9) 0.9766(3) 0.0341(6) Uani 1 1 d . . . . .
H7 H 0.1321 0.1388 0.8884 0.041 Uiso 1 1 calc R U . . .
C8 C 0.2293(5) 0.14352(12) 1.1303(4) 0.0546(9) Uani 1 1 d . . . . .
H8A H 0.2558 0.1765 1.135 0.082 Uiso 1 1 calc R U . . .
H8B H 0.3465 0.1267 1.1325 0.082 Uiso 1 1 calc R U . . .
H8C H 0.184 0.1346 1.2208 0.082 Uiso 1 1 calc R U . . .
C9 C -0.1300(5) 0.06475(11) 1.1132(4) 0.0499(8) Uani 1 1 d . . . . .
C10 C -0.1949(4) 0.14020(9) 0.6435(3) 0.0324(6) Uani 1 1 d . . . . .
H10 H -0.1433 0.1092 0.68 0.039 Uiso 1 1 calc R U . . .
C11 C -0.3682(4) 0.13244(11) 0.4990(4) 0.0444(8) Uani 1 1 d . . . . .
H11A H -0.4681 0.1158 0.5313 0.067 Uiso 1 1 calc R U . . .
H11B H -0.3279 0.1146 0.4197 0.067 Uiso 1 1 calc R U . . .
H11C H -0.4183 0.1621 0.4543 0.067 Uiso 1 1 calc R U . . .
C12 C -0.1343(4) 0.22407(11) 0.4877(4) 0.0363(7) Uani 1 1 d . . . . .
C13 C 0.4003(6) 0.05161(15) 0.7768(5) 0.0743(12) Uani 1 1 d . . . . .
H13 H 0.4545 0.0598 0.8835 0.089 Uiso 1 1 calc R U . . .
C14 C 0.5126(5) 0.02576(14) 0.7014(4) 0.0608(10) Uani 1 1 d . . . . .
H14 H 0.6376 0.0166 0.7582 0.073 Uiso 1 1 calc R U . . .
C15 C 0.4415(4) 0.01343(10) 0.5435(4) 0.0364(7) Uani 1 1 d . . . . .
C16 C 0.2538(5) 0.02780(12) 0.4712(5) 0.0587(10) Uani 1 1 d . . . . .
H16 H 0.1955 0.0203 0.3644 0.07 Uiso 1 1 calc R U . . .
C17 C 0.1525(6) 0.05321(13) 0.5566(5) 0.0670(11) Uani 1 1 d . . . . .
H17 H 0.026 0.0623 0.5037 0.08 Uiso 1 1 calc R U . . .
N1 N -0.2253(6) 0.06381(12) 1.1975(5) 0.0811(11) Uani 1 1 d . . . . .
N2 N -0.2258(4) 0.25554(9) 0.4320(3) 0.0512(7) Uani 1 1 d . . . . .
N3 N 0.2210(4) 0.06551(11) 0.7072(4) 0.0636(9) Uani 1 1 d . . . . .
Se1 Se 0.01760(5) 0.06304(2) 0.96880(4) 0.04117(10) Uani 1 1 d . . . . .
Se2 Se 0.01672(4) 0.17379(2) 0.57525(4) 0.03932(10) Uani 1 1 d . . . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.389(4) . ?
C1 C2 1.401(4) . ?
C1 C7 1.503(4) . ?
C2 C3 1.392(4) . ?
C2 C10 1.514(4) . ?
C3 C4 1.378(4) . ?
C3 H3 0.93 . ?
C4 C5 1.363(4) . ?
C4 H4 0.93 . ?
C5 C6 1.381(4) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.516(4) . ?
C7 Se1 2.019(3) . ?
C7 H7 0.98 . ?
C8 H8A 0.96 . ?
C8 H8B 0.96 . ?
C8 H8C 0.96 . ?
C9 N1 1.124(4) . ?
C9 Se1 1.840(4) . ?
C10 C11 1.517(4) . ?
C10 Se2 2.007(3) . ?
C10 H10 0.98 . ?
C11 H11A 0.96 . ?
C11 H11B 0.96 . ?
C11 H11C 0.96 . ?
C12 N2 1.139(4) . ?
C12 Se2 1.832(3) . ?
C13 N3 1.317(5) . ?
C13 C14 1.377(5) . ?
C13 H13 0.93 . ?
C14 C15 1.369(4) . ?
C14 H14 0.93 . ?
C15 C16 1.376(4) . ?
C15 C15 1.482(5) 3_656 ?
C16 C17 1.374(5) . ?
C16 H16 0.93 . ?
C17 N3 1.310(5) . ?
C17 H17 0.93 . ?

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 C2 118.3(3) . . ?
C6 C1 C7 119.6(3) . . ?
C2 C1 C7 122.0(2) . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 C10 118.8(3) . . ?
C1 C2 C10 122.3(2) . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 121.8(3) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
C1 C7 C8 117.3(2) . . ?
C1 C7 Se1 110.56(18) . . ?
C8 C7 Se1 109.2(2) . . ?
C1 C7 H7 106.4 . . ?
C8 C7 H7 106.4 . . ?
Se1 C7 H7 106.4 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 Se1 176.4(3) . . ?
C2 C10 C11 116.4(2) . . ?
C2 C10 Se2 110.92(18) . . ?
C11 C10 Se2 109.56(19) . . ?
C2 C10 H10 106.5 . . ?
C11 C10 H10 106.5 . . ?
Se2 C10 H10 106.5 . . ?
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 . . ?
N2 C12 Se2 178.9(3) . . ?
N3 C13 C14 124.2(4) . . ?
N3 C13 H13 117.9 . . ?
C14 C13 H13 117.9 . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 115.3(3) . . ?
C14 C15 C15 122.3(3) . 3_656 ?
C16 C15 C15 122.3(4) . 3_656 ?
C17 C16 C15 120.0(3) . . ?
C17 C16 H16 120 . . ?
C15 C16 H16 120 . . ?
N3 C17 C16 124.8(3) . . ?
N3 C17 H17 117.6 . . ?
C16 C17 H17 117.6 . . ?
C17 N3 C13 115.3(3) . . ?
C9 Se1 C7 95.53(13) . . ?
C12 Se2 C10 95.43(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(4) . . . . ?
C7 C1 C2 C3 -179.7(2) . . . . ?
C6 C1 C2 C10 -179.3(3) . . . . ?
C7 C1 C2 C10 1.4(4) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C10 C2 C3 C4 179.6(3) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C1 0.5(5) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C7 C1 C6 C5 179.2(3) . . . . ?
C6 C1 C7 C8 -20.5(4) . . . . ?
C2 C1 C7 C8 158.8(3) . . . . ?
C6 C1 C7 Se1 105.6(3) . . . . ?
C2 C1 C7 Se1 -75.2(3) . . . . ?
C3 C2 C10 C11 -20.6(4) . . . . ?
C1 C2 C10 C11 158.3(3) . . . . ?
C3 C2 C10 Se2 105.6(2) . . . . ?
C1 C2 C10 Se2 -75.6(3) . . . . ?
N3 C13 C14 C15 1.1(7) . . . . ?
C13 C14 C15 C16 -1.3(5) . . . . ?
C13 C14 C15 C15 178.6(4) . . . 3_656 ?
C14 C15 C16 C17 0.8(5) . . . . ?
C15 C15 C16 C17 -179.1(4) 3_656 . . . ?
C15 C16 C17 N3 -0.1(7) . . . . ?
C16 C17 N3 C13 -0.2(6) . . . . ?
C14 C13 N3 C17 -0.3(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_syn-SeCN2
_database_code_depnum_ccdc_archive 'CCDC 2040290'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2020-10-23 deposited with the CCDC.	2020-11-24 downloaded from the CCDC.
;

_audit_creation_date             2020-06-22T10:36:30-00:00
_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            'C12 H12 N2 Se2'
_chemical_formula_moiety         'C12 H12 N2 Se2'
_chemical_formula_weight         342.16

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   8.5502(6)
_cell_length_b                   7.0090(4)
_cell_length_c                   22.6261(15)
_cell_angle_alpha                90
_cell_angle_beta                 90.121(3)
_cell_angle_gamma                90
_cell_volume                     1355.94(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5533
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      23.93
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664

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

_exptl_absorpt_coefficient_mu    5.429
_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  0.344
_exptl_absorpt_correction_T_max  0.897

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.4069  0.7456                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   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      0.109797
_diffrn_orient_matrix_ub_12      -0.008853
_diffrn_orient_matrix_ub_13      -0.014888
_diffrn_orient_matrix_ub_21      0.006826
_diffrn_orient_matrix_ub_22      -0.134223
_diffrn_orient_matrix_ub_23      0.014766
_diffrn_orient_matrix_ub_31      -0.039707
_diffrn_orient_matrix_ub_32      -0.047555
_diffrn_orient_matrix_ub_33      -0.038906
_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  0.0753
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_number            22207
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.548
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_reflns_Friedel_coverage         0
_reflns_number_total             3062
_reflns_number_gt                1862
_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    'SIR-97 (Altomare et al., 1999)'
_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     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0217P)²+2.6924P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3062
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1128
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.41
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.079

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


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3682(5) -0.0080(6) 0.35605(19) 0.0367(10) Uani 1 1 d . . . . .
C2 C 0.2409(5) -0.1143(6) 0.3774(2) 0.0381(11) Uani 1 1 d . . . . .
C3 C 0.0974(6) -0.1005(8) 0.3487(3) 0.0589(15) Uani 1 1 d . . . . .
H3 H 0.0134 -0.172 0.3625 0.071 Uiso 1 1 calc R U . . .
C4 C 0.0766(7) 0.0157(8) 0.3006(3) 0.0701(17) Uani 1 1 d . . . . .
H4 H -0.0207 0.024 0.2824 0.084 Uiso 1 1 calc R U . . .
C5 C 0.1993(7) 0.1187(8) 0.2799(2) 0.0595(15) Uani 1 1 d . . . . .
H5 H 0.1859 0.1978 0.2473 0.071 Uiso 1 1 calc R U . . .
C6 C 0.3424(6) 0.1067(7) 0.3067(2) 0.0460(12) Uani 1 1 d . . . . .
H6 H 0.4251 0.1773 0.2915 0.055 Uiso 1 1 calc R U . . .
C7 C 0.5281(6) -0.0178(7) 0.3831(2) 0.0434(11) Uani 1 1 d . . . . .
H7 H 0.5131 -0.0405 0.4254 0.052 Uiso 1 1 calc R U . . .
C8 C 0.6302(6) 0.1595(8) 0.3778(3) 0.0592(15) Uani 1 1 d . . . . .
H8A H 0.6515 0.1843 0.3368 0.089 Uiso 1 1 calc R U . . .
H8B H 0.7268 0.1392 0.3985 0.089 Uiso 1 1 calc R U . . .
H8C H 0.5765 0.2668 0.3946 0.089 Uiso 1 1 calc R U . . .
C9 C 0.6626(7) -0.1458(8) 0.2765(3) 0.0617(16) Uani 1 1 d . . . . .
C10 C 0.2547(6) -0.2427(7) 0.4308(2) 0.0458(11) Uani 1 1 d . . . . .
H10 H 0.3605 -0.2309 0.4471 0.055 Uiso 1 1 calc R U . . .
C11 C 0.1401(8) -0.2138(9) 0.4789(2) 0.0774(19) Uani 1 1 d . . . . .
H11A H 0.1578 -0.092 0.4971 0.116 Uiso 1 1 calc R U . . .
H11B H 0.1522 -0.3128 0.5079 0.116 Uiso 1 1 calc R U . . .
H11C H 0.0361 -0.2179 0.4629 0.116 Uiso 1 1 calc R U . . .
C12 C 0.2952(8) -0.6330(8) 0.4641(3) 0.0666(17) Uani 1 1 d . . . . .
N1 N 0.6710(7) -0.0788(8) 0.2307(3) 0.0822(17) Uani 1 1 d . . . . .
N2 N 0.3384(8) -0.7125(9) 0.5039(3) 0.097(2) Uani 1 1 d . . . . .
Se1 Se 0.64601(6) -0.24212(9) 0.35180(3) 0.0599(2) Uani 1 1 d . . . . .
Se2 Se 0.22842(9) -0.50492(9) 0.39764(3) 0.0745(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 C6 1.393(6) . ?
C1 C2 1.406(6) . ?
C1 C7 1.498(6) . ?
C2 C3 1.390(7) . ?
C2 C10 1.510(6) . ?
C3 C4 1.370(8) . ?
C3 H3 0.93 . ?
C4 C5 1.358(8) . ?
C4 H4 0.93 . ?
C5 C6 1.367(7) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.523(7) . ?
C7 Se1 1.998(5) . ?
C7 H7 0.98 . ?
C8 H8A 0.96 . ?
C8 H8B 0.96 . ?
C8 H8C 0.96 . ?
C9 N1 1.141(8) . ?
C9 Se1 1.838(7) . ?
C10 C11 1.480(7) . ?
C10 Se2 1.997(5) . ?
C10 H10 0.98 . ?
C11 H11A 0.96 . ?
C11 H11B 0.96 . ?
C11 H11C 0.96 . ?
C12 N2 1.120(7) . ?
C12 Se2 1.841(7) . ?

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 C2 117.4(4) . . ?
C6 C1 C7 119.8(4) . . ?
C2 C1 C7 122.8(4) . . ?
C3 C2 C1 119.0(4) . . ?
C3 C2 C10 118.9(4) . . ?
C1 C2 C10 122.1(4) . . ?
C4 C3 C2 121.7(5) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C5 C4 C3 119.4(5) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.4(5) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 122.1(5) . . ?
C5 C6 H6 119 . . ?
C1 C6 H6 119 . . ?
C1 C7 C8 116.9(4) . . ?
C1 C7 Se1 110.6(3) . . ?
C8 C7 Se1 108.9(3) . . ?
C1 C7 H7 106.6 . . ?
C8 C7 H7 106.6 . . ?
Se1 C7 H7 106.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 Se1 177.1(6) . . ?
C11 C10 C2 117.1(5) . . ?
C11 C10 Se2 109.1(4) . . ?
C2 C10 Se2 103.9(3) . . ?
C11 C10 H10 108.8 . . ?
C2 C10 H10 108.8 . . ?
Se2 C10 H10 108.8 . . ?
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 . . ?
N2 C12 Se2 178.5(6) . . ?
C9 Se1 C7 94.5(2) . . ?
C12 Se2 C10 96.2(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.1(7) . . . . ?
C7 C1 C2 C3 -178.3(5) . . . . ?
C6 C1 C2 C10 -179.7(4) . . . . ?
C7 C1 C2 C10 1.9(7) . . . . ?
C1 C2 C3 C4 -0.8(8) . . . . ?
C10 C2 C3 C4 179.0(5) . . . . ?
C2 C3 C4 C5 0.8(9) . . . . ?
C3 C4 C5 C6 0.0(9) . . . . ?
C4 C5 C6 C1 -0.7(8) . . . . ?
C2 C1 C6 C5 0.7(7) . . . . ?
C7 C1 C6 C5 179.1(5) . . . . ?
C6 C1 C7 C8 30.2(6) . . . . ?
C2 C1 C7 C8 -151.5(5) . . . . ?
C6 C1 C7 Se1 -95.3(4) . . . . ?
C2 C1 C7 Se1 83.1(5) . . . . ?
C3 C2 C10 C11 -52.9(7) . . . . ?
C1 C2 C10 C11 126.9(5) . . . . ?
C3 C2 C10 Se2 67.5(5) . . . . ?
C1 C2 C10 Se2 -112.8(4) . . . . ?

####################################################################### 
# 
# 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 2040296'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;Universite Rennes
France
;
_audit_update_record             
;
2020-11-17 deposited with the CCDC.	2020-11-24 downloaded from the CCDC.
;

_audit_creation_date             2020-11-17T09:26:30-00:00
_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_moiety         'C16 H22 Cl0.50 N2.50 Se2'
_chemical_formula_sum            'C16 H22 Cl0.50 N2.50 Se2'
_chemical_formula_weight         425

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

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

_cell_length_a                   9.0534(5)
_cell_length_b                   13.1176(6)
_cell_length_c                   16.4261(7)
_cell_angle_alpha                90
_cell_angle_beta                 112.672(2)
_cell_angle_gamma                90
_cell_volume                     1800.00(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2762
_cell_measurement_theta_min      2.4384
_cell_measurement_theta_max      22.9794
_cell_measurement_wavelength     0.71073


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

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848

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

_exptl_absorpt_coefficient_mu    4.179
_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  0.366
_exptl_absorpt_correction_T_max  0.959

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.552821  0.745553              #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------#

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

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_unetI/netI     0.1411
_diffrn_reflns_number            4121
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.688
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             4121
_reflns_number_gt                2069
_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    'SIR-92 (Altomare et al., 1994)'
_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_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)+(0.0756P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4121
_refine_ls_number_parameters     231
_refine_ls_number_restraints     12
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1583
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1591
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.133

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


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.9436(7) 0.1570(3) 0.7560(3) 0.0325(12) Uani 1 1 d . . . . .
C2 C 1.1101(7) 0.1548(4) 0.7959(3) 0.0336(12) Uani 1 1 d . . . . .
C3 C 1.1993(8) 0.2180(4) 0.7635(4) 0.0502(16) Uani 1 1 d . . . . .
H3 H 1.3105 0.2169 0.7901 0.06 Uiso 1 1 calc R U . . .
C4 C 1.1247(10) 0.2819(4) 0.6927(4) 0.0571(19) Uani 1 1 d . . . . .
H4 H 1.1862 0.3234 0.6722 0.069 Uiso 1 1 calc R U . . .
C5 C 0.9603(9) 0.2847(4) 0.6522(4) 0.0545(18) Uani 1 1 d . . . . .
H5 H 0.9099 0.3276 0.6044 0.065 Uiso 1 1 calc R U . . .
C6 C 0.8717(8) 0.2219(4) 0.6845(3) 0.0434(15) Uani 1 1 d . . . . .
H6 H 0.7606 0.2232 0.6574 0.052 Uiso 1 1 calc R U . . .
C7 C 0.8374(7) 0.0915(4) 0.7869(3) 0.0443(15) Uani 1 1 d . . . . .
H7 H 0.9033 0.0333 0.8176 0.053 Uiso 1 1 calc R U . . .
C8 C 0.6892(8) 0.0464(5) 0.7158(4) 0.0613(18) Uani 1 1 d . . . . .
H8A H 0.6175 0.1003 0.6854 0.092 Uiso 1 1 calc R U . . .
H8B H 0.6368 0.0016 0.7424 0.092 Uiso 1 1 calc R U . . .
H8C H 0.7198 0.0088 0.6746 0.092 Uiso 1 1 calc R U . . .
C9 C 0.6405(9) 0.2541(5) 0.7965(5) 0.0600(18) Uani 1 1 d . . . . .
C10 C 1.2002(7) 0.0836(4) 0.8712(3) 0.0401(14) Uani 1 1 d . . . . .
H10 H 1.1238 0.0302 0.8701 0.048 Uiso 1 1 calc R U . . .
C11 C 1.3428(8) 0.0286(5) 0.8650(4) 0.0602(18) Uani 1 1 d . . . . .
H11A H 1.3092 -0.009 0.8107 0.09 Uiso 1 1 calc R U . . .
H11B H 1.3867 -0.0175 0.9139 0.09 Uiso 1 1 calc R U . . .
H11C H 1.4228 0.0775 0.8666 0.09 Uiso 1 1 calc R U . . .
C12 C 1.4222(10) 0.2342(6) 0.9787(4) 0.067(2) Uani 1 1 d . . . . .
C13 C 0.9808(17) 0.4910(9) 1.0857(7) 0.054(4) Uani 0.5 1 d . . P A -1
H13A H 0.8713 0.4699 1.0724 0.065 Uiso 0.5 1 calc R U P A -1
H13B H 1.0488 0.4352 1.1177 0.065 Uiso 0.5 1 calc R U P A -1
C17A C 1.012(3) 0.5745(17) 1.1455(17) 0.043(5) Uani 0.5 1 d . U P A -1
H17A H 0.9932 0.554 1.1967 0.065 Uiso 0.5 1 calc R U P A -1
H17B H 1.1217 0.5954 1.1629 0.065 Uiso 0.5 1 calc R U P A -1
H17C H 0.9429 0.6304 1.1172 0.065 Uiso 0.5 1 calc R U P A -1
C15 C 1.1724(16) 0.5524(9) 1.0213(8) 0.056(3) Uani 0.5 1 d . . P A -1
H15A H 1.1821 0.5689 0.966 0.067 Uiso 0.5 1 calc R U P A -1
H15B H 1.1768 0.616 1.0524 0.067 Uiso 0.5 1 calc R U P A -1
C18A C 1.309(3) 0.4895(17) 1.074(2) 0.086(7) Uani 0.5 1 d . U P A -1
H18A H 1.4066 0.5257 1.084 0.129 Uiso 0.5 1 calc R U P A -1
H18B H 1.3025 0.4743 1.1298 0.129 Uiso 0.5 1 calc R U P A -1
H18C H 1.3078 0.4271 1.0433 0.129 Uiso 0.5 1 calc R U P A -1
C14 C 1.0159(15) 0.5920(8) 1.0454(6) 0.040(3) Uani 0.5 1 d . . P A -2
H14A H 0.9512 0.6421 1.0033 0.049 Uiso 0.5 1 calc R U P A -2
H14B H 1.1265 0.6134 1.0633 0.049 Uiso 0.5 1 calc R U P A -2
C16 C 1.1099(17) 0.4114(9) 1.0547(7) 0.056(3) Uani 0.5 1 d . . P A -2
H16A H 1.0837 0.3963 1.1054 0.067 Uiso 0.5 1 calc R U P A -2
H16B H 1.0901 0.3505 1.0185 0.067 Uiso 0.5 1 calc R U P A -2
C17B C 0.973(3) 0.5993(17) 1.1269(15) 0.039(5) Uani 0.5 1 d . U P A -2
H17D H 0.9915 0.6677 1.1495 0.059 Uiso 0.5 1 calc R U P A -2
H17E H 0.8628 0.5819 1.1109 0.059 Uiso 0.5 1 calc R U P A -2
H17F H 1.0393 0.5531 1.1713 0.059 Uiso 0.5 1 calc R U P A -2
C18B C 1.279(3) 0.439(2) 1.085(2) 0.099(9) Uani 0.5 1 d . U P A -2
H18D H 1.3431 0.3833 1.1178 0.149 Uiso 0.5 1 calc R U P A -2
H18E H 1.3052 0.4526 1.0345 0.149 Uiso 0.5 1 calc R U P A -2
H18F H 1.2989 0.4983 1.1213 0.149 Uiso 0.5 1 calc R U P A -2
N1 N 0.5569(9) 0.3131(5) 0.7498(5) 0.093(2) Uani 1 1 d . . . . .
N2 N 1.5228(10) 0.2849(6) 0.9776(4) 0.105(3) Uani 1 1 d . . . . .
N3 N 1 0.5 1 0.0396(16) Uani 1 2 d S . P . .
Cl1 Cl 1 0 1 0.0596(7) Uani 1 2 d S . P . .
Se1 Se 0.77372(8) 0.16239(4) 0.87611(4) 0.0506(2) Uani 1 1 d . . . . .
Se2 Se 1.26263(8) 0.15187(5) 0.98892(4) 0.0543(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 C6 1.392(7) . ?
C1 C2 1.393(8) . ?
C1 C7 1.516(7) . ?
C2 C3 1.397(7) . ?
C2 C10 1.513(7) . ?
C3 C4 1.381(8) . ?
C3 H3 0.93 . ?
C4 C5 1.377(9) . ?
C4 H4 0.93 . ?
C5 C6 1.390(8) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.518(7) . ?
C7 Se1 2.000(5) . ?
C7 H7 0.98 . ?
C8 H8A 0.96 . ?
C8 H8B 0.96 . ?
C8 H8C 0.96 . ?
C9 N1 1.145(8) . ?
C9 Se1 1.843(8) . ?
C10 C11 1.516(8) . ?
C10 Se2 2.005(5) . ?
C10 H10 0.98 . ?
C11 H11A 0.96 . ?
C11 H11B 0.96 . ?
C11 H11C 0.96 . ?
C12 N2 1.134(9) . ?
C12 Se2 1.862(9) . ?
C13 C17A 1.42(3) . ?
C13 N3 1.488(10) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C17A H17A 0.96 . ?
C17A H17B 0.96 . ?
C17A H17C 0.96 . ?
C15 C18A 1.46(3) . ?
C15 N3 1.616(13) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C18A H18A 0.96 . ?
C18A H18B 0.96 . ?
C18A H18C 0.96 . ?
C14 N3 1.397(10) . ?
C14 C17B 1.53(3) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C16 C18B 1.46(3) . ?
C16 N3 1.568(11) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C17B H17D 0.96 . ?
C17B H17E 0.96 . ?
C17B H17F 0.96 . ?
C18B H18D 0.96 . ?
C18B H18E 0.96 . ?
C18B H18F 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 C2 118.6(5) . . ?
C6 C1 C7 118.6(5) . . ?
C2 C1 C7 122.8(5) . . ?
C1 C2 C3 119.2(5) . . ?
C1 C2 C10 122.8(5) . . ?
C3 C2 C10 117.9(5) . . ?
C4 C3 C2 120.9(6) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 120.7(6) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 118.4(6) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 122.2(6) . . ?
C5 C6 H6 118.9 . . ?
C1 C6 H6 118.9 . . ?
C1 C7 C8 116.7(4) . . ?
C1 C7 Se1 112.4(3) . . ?
C8 C7 Se1 109.1(4) . . ?
C1 C7 H7 106 . . ?
C8 C7 H7 106 . . ?
Se1 C7 H7 106 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 Se1 177.2(7) . . ?
C2 C10 C11 116.3(5) . . ?
C2 C10 Se2 112.0(3) . . ?
C11 C10 Se2 110.3(4) . . ?
C2 C10 H10 105.8 . . ?
C11 C10 H10 105.8 . . ?
Se2 C10 H10 105.8 . . ?
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 . . ?
N2 C12 Se2 176.1(7) . . ?
C17A C13 N3 121.8(13) . . ?
C17A C13 H13A 106.9 . . ?
N3 C13 H13A 106.9 . . ?
C17A C13 H13B 106.9 . . ?
N3 C13 H13B 106.9 . . ?
H13A C13 H13B 106.7 . . ?
C13 C17A H17A 109.5 . . ?
C13 C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C13 C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C18A C15 N3 114.4(11) . . ?
C18A C15 H15A 108.6 . . ?
N3 C15 H15A 108.6 . . ?
C18A C15 H15B 108.6 . . ?
N3 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C15 C18A H18A 109.5 . . ?
C15 C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C15 C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
N3 C14 C17B 120.8(12) . . ?
N3 C14 H14A 107.1 . . ?
C17B C14 H14A 107.1 . . ?
N3 C14 H14B 107.1 . . ?
C17B C14 H14B 107.1 . . ?
H14A C14 H14B 106.8 . . ?
C18B C16 N3 111.2(14) . . ?
C18B C16 H16A 109.4 . . ?
N3 C16 H16A 109.4 . . ?
C18B C16 H16B 109.4 . . ?
N3 C16 H16B 109.4 . . ?
H16A C16 H16B 108 . . ?
C14 C17B H17D 109.5 . . ?
C14 C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C14 C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C16 C18B H18D 109.5 . . ?
C16 C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C16 C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C14 N3 C16 115.0(6) . . ?
C13 N3 C15 106.5(7) . . ?
C9 Se1 C7 94.5(3) . . ?
C12 Se2 C10 96.5(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
C6 C1 C2 C3 0.5(7) . . . . ?
C7 C1 C2 C3 -179.8(4) . . . . ?
C6 C1 C2 C10 -177.0(4) . . . . ?
C7 C1 C2 C10 2.7(7) . . . . ?
C1 C2 C3 C4 -0.2(8) . . . . ?
C10 C2 C3 C4 177.4(5) . . . . ?
C2 C3 C4 C5 -0.1(9) . . . . ?
C3 C4 C5 C6 0.1(8) . . . . ?
C4 C5 C6 C1 0.2(8) . . . . ?
C2 C1 C6 C5 -0.5(7) . . . . ?
C7 C1 C6 C5 179.8(5) . . . . ?
C6 C1 C7 C8 38.5(7) . . . . ?
C2 C1 C7 C8 -141.2(5) . . . . ?
C6 C1 C7 Se1 -88.5(5) . . . . ?
C2 C1 C7 Se1 91.7(5) . . . . ?
C1 C2 C10 C11 135.0(6) . . . . ?
C3 C2 C10 C11 -42.5(7) . . . . ?
C1 C2 C10 Se2 -96.9(5) . . . . ?
C3 C2 C10 Se2 85.6(5) . . . . ?
C17B C14 N3 C16 -63.1(15) . . . . ?
C17A C13 N3 C15 48.0(16) . . . . ?
C18B C16 N3 C14 -59.8(17) . . . . ?
C18A C15 N3 C13 66.9(16) . . . . ?

####################################################################### 
# 
# 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_anti-Br2
_database_code_depnum_ccdc_archive 'CCDC 2040291'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2020-10-23 deposited with the CCDC.	2020-11-24 downloaded from the CCDC.
;

_audit_creation_date             2018-10-12T16:10:39-00:00
_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 Br2'
_chemical_formula_moiety         'C10 H12 Br2'
_chemical_formula_weight         292.02

#----------------------------------------------------------------------------#
#                   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                   8.2203(8)
_cell_length_b                   14.6643(16)
_cell_length_c                   9.4380(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.312(3)
_cell_angle_gamma                90
_cell_volume                     1066.96(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7372
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      27.49
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.818
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568

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

_exptl_absorpt_coefficient_mu    7.544
_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  0.447
_exptl_absorpt_correction_T_max  0.860

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.5360  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------#

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

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      -0.00292
_diffrn_orient_matrix_ub_12      -0.060446
_diffrn_orient_matrix_ub_13      -0.049873
_diffrn_orient_matrix_ub_21      0.068855
_diffrn_orient_matrix_ub_22      0.026003
_diffrn_orient_matrix_ub_23      -0.059376
_diffrn_orient_matrix_ub_31      0.109895
_diffrn_orient_matrix_ub_32      -0.017899
_diffrn_orient_matrix_ub_33      0.082169
_diffrn_measurement_device_type  'D8 VENTURE 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     0.0273
_diffrn_reflns_number            19035
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.778
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             2439
_reflns_number_gt                1943
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0253P)²+0.0163P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2439
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.022
_refine_ls_wR_factor_ref         0.0513
_refine_ls_wR_factor_gt          0.0484
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.78
_refine_diff_density_rms         0.083

#----------------------------------------------------------------------------#
#                   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'

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
Br2 Br 0.36406(2) 0.10322(2) 0.53373(2) 0.02150(7) Uani 1 1 d . . . . .
Br1 Br 0.89259(2) 0.10357(2) 0.40962(2) 0.02059(7) Uani 1 1 d . . . . .
C4 C 0.6331(3) 0.40118(14) 0.5587(3) 0.0273(5) Uani 1 1 d . . . . .
H4 H 0.630374 0.456075 0.611335 0.033 Uiso 1 1 calc R U . . .
C3 C 0.6514(3) 0.40405(15) 0.4182(3) 0.0285(5) Uani 1 1 d . . . . .
H3 H 0.660526 0.461025 0.373596 0.034 Uiso 1 1 calc R U . . .
C6 C 0.62395(19) 0.23628(13) 0.54873(18) 0.0134(4) Uani 1 1 d . . . . .
C1 C 0.64367(19) 0.23902(13) 0.40570(19) 0.0140(4) Uani 1 1 d . . . . .
C5 C 0.6187(2) 0.31776(14) 0.6218(2) 0.0202(4) Uani 1 1 d . . . . .
H5 H 0.604896 0.316201 0.717574 0.024 Uiso 1 1 calc R U . . .
C9 C 0.6101(2) 0.14696(13) 0.6225(2) 0.0152(4) Uani 1 1 d . . . . .
H9 H 0.68667 0.101555 0.597371 0.018 Uiso 1 1 calc R U . . .
C10 C 0.6561(3) 0.14832(15) 0.7930(2) 0.0252(5) Uani 1 1 d . . . . .
H10A H 0.77594 0.169391 0.840891 0.038 Uiso 1 1 calc R U . . .
H10B H 0.644687 0.086715 0.828702 0.038 Uiso 1 1 calc R U . . .
H10C H 0.577516 0.189731 0.819423 0.038 Uiso 1 1 calc R U . . .
C2 C 0.6564(2) 0.32353(14) 0.3430(2) 0.0216(4) Uani 1 1 d . . . . .
H2 H 0.668794 0.326014 0.246689 0.026 Uiso 1 1 calc R U . . .
C8 C 0.6075(3) 0.16068(16) 0.1521(2) 0.0264(5) Uani 1 1 d . . . . .
H8A H 0.491609 0.187212 0.106082 0.04 Uiso 1 1 calc R U . . .
H8B H 0.609852 0.099974 0.109423 0.04 Uiso 1 1 calc R U . . .
H8C H 0.693113 0.199921 0.131353 0.04 Uiso 1 1 calc R U . . .
C7 C 0.6509(2) 0.15279(14) 0.3221(2) 0.0160(4) Uani 1 1 d . . . . .
H7 H 0.569912 0.107525 0.341221 0.019 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
Br2 C9 2.0068(16) . ?
Br1 C7 2.0028(17) . ?
C4 C5 1.383(3) . ?
C4 C3 1.387(3) . ?
C4 H4 0.95 . ?
C3 C2 1.385(3) . ?
C3 H3 0.95 . ?
C6 C5 1.387(3) . ?
C6 C1 1.415(2) . ?
C6 C9 1.506(3) . ?
C1 C2 1.393(3) . ?
C1 C7 1.502(3) . ?
C5 H5 0.95 . ?
C9 C10 1.520(3) . ?
C9 H9 1 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C2 H2 0.95 . ?
C8 C7 1.522(3) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C7 H7 1 . ?

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 C4 C3 119.5(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C6 C1 118.89(17) . . ?
C5 C6 C9 119.91(16) . . ?
C1 C6 C9 121.20(16) . . ?
C2 C1 C6 118.74(18) . . ?
C2 C1 C7 120.21(17) . . ?
C6 C1 C7 121.05(16) . . ?
C4 C5 C6 121.74(19) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C6 C9 C10 116.56(17) . . ?
C6 C9 Br2 108.17(11) . . ?
C10 C9 Br2 106.92(12) . . ?
C6 C9 H9 108.3 . . ?
C10 C9 H9 108.3 . . ?
Br2 C9 H9 108.3 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C2 C1 121.40(19) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 C7 C8 116.88(17) . . ?
C1 C7 Br1 107.52(11) . . ?
C8 C7 Br1 107.34(12) . . ?
C1 C7 H7 108.3 . . ?
C8 C7 H7 108.3 . . ?
Br1 C7 H7 108.3 . . ?

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
C5 C4 C3 C2 -0.5(3) . . . . ?
C5 C6 C1 C2 -0.3(2) . . . . ?
C9 C6 C1 C2 -179.79(14) . . . . ?
C5 C6 C1 C7 179.73(14) . . . . ?
C9 C6 C1 C7 0.2(2) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C1 C6 C5 C4 -0.3(3) . . . . ?
C9 C6 C5 C4 179.22(15) . . . . ?
C5 C6 C9 C10 -21.6(2) . . . . ?
C1 C6 C9 C10 157.94(16) . . . . ?
C5 C6 C9 Br2 98.85(16) . . . . ?
C1 C6 C9 Br2 -81.63(17) . . . . ?
C4 C3 C2 C1 -0.1(3) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C7 C1 C2 C3 -179.52(16) . . . . ?
C2 C1 C7 C8 -21.3(2) . . . . ?
C6 C1 C7 C8 158.69(16) . . . . ?
C2 C1 C7 Br1 99.38(16) . . . . ?
C6 C1 C7 Br1 -80.61(17) . . . . ?

####################################################################### 
# 
# 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_anti-Ph4PCl
_database_code_depnum_ccdc_archive 'CCDC 2040293'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2020-10-23 deposited with the CCDC.	2020-11-24 downloaded from the CCDC.
;

_audit_creation_date             2019-01-25T15:22:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_sum            'C38 H37 Cl N2 O0.50 P Se2'
_chemical_formula_moiety         'C24 H20 P, C12 H12 N2 Se2, 0.5(C4 H10 O), Cl'
_chemical_formula_weight         754.03

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

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

_cell_length_a                   9.2775(11)
_cell_length_b                   13.5469(16)
_cell_length_c                   14.3091(15)
_cell_angle_alpha                82.498(4)
_cell_angle_beta                 88.218(4)
_cell_angle_gamma                83.497(4)
_cell_volume                     1771.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9578
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      27.3
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             766

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

_exptl_absorpt_coefficient_mu    2.238
_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  0.744
_exptl_absorpt_correction_T_max  0.799

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.5673  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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      -0.088263
_diffrn_orient_matrix_ub_12      -0.0172
_diffrn_orient_matrix_ub_13      -0.029979
_diffrn_orient_matrix_ub_21      -0.035378
_diffrn_orient_matrix_ub_22      0.072843
_diffrn_orient_matrix_ub_23      -0.013678
_diffrn_orient_matrix_ub_31      0.052253
_diffrn_orient_matrix_ub_32      0.003126
_diffrn_orient_matrix_ub_33      -0.062324
_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  0.0375
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_number            43521
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.436
_diffrn_reflns_theta_max         27.544
_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             8141
_reflns_number_gt                5829
_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    'SIR-92 (Altomare et al., 1994)'
_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_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)+(0.0439P)²+1.9504P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         8141
_refine_ls_number_parameters     425
_refine_ls_number_restraints     2
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1222
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.148
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.652
_refine_diff_density_min         -0.951
_refine_diff_density_rms         0.087

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


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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 0.3063(4) 0.8639(2) 0.4453(2) 0.0399(7) Uani 1 1 d . . . . .
C2 C 0.4509(4) 0.8393(2) 0.4750(2) 0.0399(7) Uani 1 1 d . . . . .
C3 C 0.4820(4) 0.8491(3) 0.5675(3) 0.0546(9) Uani 1 1 d . . . . .
H3 H 0.5771 0.834 0.588 0.066 Uiso 1 1 calc R U . . .
C4 C 0.3745(5) 0.8810(3) 0.6302(3) 0.0633(11) Uani 1 1 d . . . . .
H4 H 0.3981 0.8874 0.6917 0.076 Uiso 1 1 calc R U . . .
C5 C 0.2348(5) 0.9027(3) 0.6015(3) 0.0623(11) Uani 1 1 d . . . . .
H5 H 0.1622 0.9229 0.6436 0.075 Uiso 1 1 calc R U . . .
C6 C 0.2011(4) 0.8948(3) 0.5096(3) 0.0525(9) Uani 1 1 d . . . . .
H6 H 0.1055 0.9104 0.4903 0.063 Uiso 1 1 calc R U . . .
C7 C 0.2635(4) 0.8548(3) 0.3458(2) 0.0431(8) Uani 1 1 d . . . . .
H7 H 0.3183 0.7934 0.3287 0.052 Uiso 1 1 calc R U . . .
C8 C 0.1051(4) 0.8446(3) 0.3319(3) 0.0610(10) Uani 1 1 d . . . . .
H8A H 0.0766 0.789 0.3743 0.091 Uiso 1 1 calc R U . . .
H8B H 0.091 0.8335 0.2681 0.091 Uiso 1 1 calc R U . . .
H8C H 0.0471 0.9049 0.3445 0.091 Uiso 1 1 calc R U . . .
C9 C 0.2065(4) 1.0665(3) 0.3075(3) 0.0545(9) Uani 1 1 d . . . . .
C10 C 0.5687(3) 0.8038(3) 0.4095(2) 0.0418(7) Uani 1 1 d . . . . .
H10 H 0.5503 0.8439 0.3481 0.05 Uiso 1 1 calc R U . . .
C11 C 0.7226(4) 0.8156(3) 0.4347(3) 0.0648(11) Uani 1 1 d . . . . .
H11A H 0.73 0.8844 0.4413 0.097 Uiso 1 1 calc R U . . .
H11B H 0.788 0.7953 0.3856 0.097 Uiso 1 1 calc R U . . .
H11C H 0.7473 0.7745 0.493 0.097 Uiso 1 1 calc R U . . .
C12 C 0.5746(4) 0.6112(3) 0.5175(3) 0.0546(9) Uani 1 1 d . . . . .
C13 C 1.0924(3) 0.2770(2) 0.0884(2) 0.0394(7) Uani 1 1 d . . . . .
C14 C 1.2016(4) 0.2066(3) 0.0634(3) 0.0566(10) Uani 1 1 d . . . . .
H14 H 1.1823 0.161 0.0234 0.068 Uiso 1 1 calc R U . . .
C15 C 1.3388(4) 0.2041(4) 0.0979(4) 0.0738(13) Uani 1 1 d . . . . .
H15 H 1.4132 0.1579 0.0802 0.089 Uiso 1 1 calc R U . . .
C16 C 1.3653(5) 0.2696(4) 0.1583(4) 0.0779(14) Uani 1 1 d . . . . .
H16 H 1.4578 0.2669 0.1824 0.094 Uiso 1 1 calc R U . . .
C17 C 1.2578(5) 0.3394(3) 0.1840(3) 0.0695(12) Uani 1 1 d . . . . .
H17 H 1.2776 0.3834 0.2255 0.083 Uiso 1 1 calc R U . . .
C18 C 1.1200(4) 0.3446(3) 0.1482(3) 0.0485(8) Uani 1 1 d . . . . .
H18 H 1.0471 0.3928 0.1641 0.058 Uiso 1 1 calc R U . . .
C19 C 0.9274(4) 0.3266(2) -0.0886(2) 0.0380(7) Uani 1 1 d . . . . .
C20 C 1.0620(4) 0.3352(3) -0.1326(3) 0.0558(10) Uani 1 1 d . . . . .
H20 H 1.1469 0.3166 -0.0988 0.067 Uiso 1 1 calc R U . . .
C21 C 1.0679(6) 0.3716(4) -0.2270(3) 0.0790(15) Uani 1 1 d . . . . .
H21 H 1.1574 0.3778 -0.257 0.095 Uiso 1 1 calc R U . . .
C22 C 0.9427(6) 0.3989(4) -0.2771(3) 0.0791(15) Uani 1 1 d . . . . .
H22 H 0.9479 0.4246 -0.3405 0.095 Uiso 1 1 calc R U . . .
C23 C 0.8099(5) 0.3884(3) -0.2344(3) 0.0621(11) Uani 1 1 d . . . . .
H23 H 0.7257 0.4057 -0.2692 0.075 Uiso 1 1 calc R U . . .
C24 C 0.8011(4) 0.3526(3) -0.1404(2) 0.0458(8) Uani 1 1 d . . . . .
H24 H 0.7111 0.3457 -0.1114 0.055 Uiso 1 1 calc R U . . .
C25 C 0.7915(3) 0.3692(2) 0.0912(2) 0.0377(7) Uani 1 1 d . . . . .
C26 C 0.7435(4) 0.4633(3) 0.0475(3) 0.0506(9) Uani 1 1 d . . . . .
H26 H 0.7748 0.4843 -0.0135 0.061 Uiso 1 1 calc R U . . .
C27 C 0.6482(5) 0.5268(3) 0.0949(4) 0.0670(12) Uani 1 1 d . . . . .
H27 H 0.6143 0.59 0.0652 0.08 Uiso 1 1 calc R U . . .
C28 C 0.6038(4) 0.4968(4) 0.1852(4) 0.0691(13) Uani 1 1 d . . . . .
H28 H 0.5401 0.5398 0.2166 0.083 Uiso 1 1 calc R U . . .
C29 C 0.6527(4) 0.4042(4) 0.2294(3) 0.0666(12) Uani 1 1 d . . . . .
H29 H 0.6232 0.3847 0.2911 0.08 Uiso 1 1 calc R U . . .
C30 C 0.7460(4) 0.3390(3) 0.1827(3) 0.0510(9) Uani 1 1 d . . . . .
H30 H 0.7779 0.2755 0.2126 0.061 Uiso 1 1 calc R U . . .
C31 C 0.8546(3) 0.1613(2) 0.0564(2) 0.0353(7) Uani 1 1 d . . . . .
C32 C 0.7523(4) 0.1358(3) -0.0018(3) 0.0481(8) Uani 1 1 d . . . . .
H32 H 0.7248 0.1783 -0.0562 0.058 Uiso 1 1 calc R U . . .
C33 C 0.6911(4) 0.0473(3) 0.0207(3) 0.0559(10) Uani 1 1 d . . . . .
H33 H 0.6222 0.0306 -0.0186 0.067 Uiso 1 1 calc R U . . .
C34 C 0.7310(5) -0.0163(3) 0.1008(3) 0.0553(10) Uani 1 1 d . . . . .
H34 H 0.689 -0.0756 0.116 0.066 Uiso 1 1 calc R U . . .
C35 C 0.8327(5) 0.0085(3) 0.1575(3) 0.0672(12) Uani 1 1 d . . . . .
H35 H 0.8597 -0.0343 0.2119 0.081 Uiso 1 1 calc R U . . .
C36 C 0.8965(5) 0.0963(3) 0.1359(3) 0.0585(10) Uani 1 1 d . . . . .
H36 H 0.9674 0.1114 0.1746 0.07 Uiso 1 1 calc R U . . .
C37A C 0.1111(12) 0.5520(9) 0.5322(8) 0.074(3) Uani 0.5 1 d D . P A 1
H37A H 0.177 0.5669 0.4796 0.089 Uiso 0.5 1 calc R U P A 1
H37B H 0.1658 0.5065 0.5797 0.089 Uiso 0.5 1 calc R U P A 1
C38A C 0.065(2) 0.6481(11) 0.5730(16) 0.082(4) Uani 0.5 1 d D . P A 1
H38A H 0.0123 0.695 0.5267 0.122 Uiso 0.5 1 calc R U P A 1
H38B H 0.1493 0.6758 0.5908 0.122 Uiso 0.5 1 calc R U P A 1
H38C H 0.0039 0.6345 0.6276 0.122 Uiso 0.5 1 calc R U P A 1
C37B C -0.0315(12) 0.5821(7) 0.5298(7) 0.079(3) Uani 0.5 1 d D . P A 2
H37C H -0.0991 0.5764 0.5828 0.095 Uiso 0.5 1 calc R U P A 2
H37D H -0.0735 0.6323 0.4806 0.095 Uiso 0.5 1 calc R U P A 2
C38B C 0.113(2) 0.6078(15) 0.5597(17) 0.113(8) Uani 0.5 1 d D . P A 2
H38D H 0.15 0.5592 0.6108 0.169 Uiso 0.5 1 calc R U P A 2
H38E H 0.1012 0.6731 0.5799 0.169 Uiso 0.5 1 calc R U P A 2
H38F H 0.1807 0.6074 0.5074 0.169 Uiso 0.5 1 calc R U P A 2
N1 N 0.1326(5) 1.1265(3) 0.3386(3) 0.0801(11) Uani 1 1 d . . . . .
N2 N 0.5884(5) 0.5769(3) 0.5941(3) 0.0764(11) Uani 1 1 d . . . . .
P1 P 0.91718(8) 0.28331(6) 0.03538(5) 0.03270(17) Uani 1 1 d . . . . .
Cl1 Cl 0.52052(10) 0.77265(7) 0.17539(6) 0.0486(2) Uani 1 1 d . . . . .
Se1 Se 0.32548(4) 0.96757(3) 0.25432(3) 0.05393(12) Uani 1 1 d . . . . .
Se2 Se 0.55318(4) 0.66098(3) 0.39110(3) 0.04750(11) Uani 1 1 d . . . . .
O1 O 0 0.5 0.5 0.0780(15) Uani 1 2 d DS . P . .



#----------------------------------------------------------------------------#
#                   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 1.388(5) . ?
C1 C2 1.410(5) . ?
C1 C7 1.513(5) . ?
C2 C3 1.390(5) . ?
C2 C10 1.496(5) . ?
C3 C4 1.391(6) . ?
C3 H3 0.93 . ?
C4 C5 1.361(6) . ?
C4 H4 0.93 . ?
C5 C6 1.382(6) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.513(5) . ?
C7 Se1 2.002(3) . ?
C7 H7 0.98 . ?
C8 H8A 0.96 . ?
C8 H8B 0.96 . ?
C8 H8C 0.96 . ?
C9 N1 1.130(5) . ?
C9 Se1 1.864(5) . ?
C10 C11 1.514(5) . ?
C10 Se2 2.008(3) . ?
C10 H10 0.98 . ?
C11 H11A 0.96 . ?
C11 H11B 0.96 . ?
C11 H11C 0.96 . ?
C12 N2 1.139(5) . ?
C12 Se2 1.854(4) . ?
C13 C18 1.381(5) . ?
C13 C14 1.383(5) . ?
C13 P1 1.803(3) . ?
C14 C15 1.375(6) . ?
C14 H14 0.93 . ?
C15 C16 1.362(7) . ?
C15 H15 0.93 . ?
C16 C17 1.371(7) . ?
C16 H16 0.93 . ?
C17 C18 1.383(5) . ?
C17 H17 0.93 . ?
C18 H18 0.93 . ?
C19 C20 1.391(5) . ?
C19 C24 1.392(5) . ?
C19 P1 1.797(3) . ?
C20 C21 1.378(5) . ?
C20 H20 0.93 . ?
C21 C22 1.373(7) . ?
C21 H21 0.93 . ?
C22 C23 1.371(6) . ?
C22 H22 0.93 . ?
C23 C24 1.372(5) . ?
C23 H23 0.93 . ?
C24 H24 0.93 . ?
C25 C26 1.377(5) . ?
C25 C30 1.389(5) . ?
C25 P1 1.796(3) . ?
C26 C27 1.387(5) . ?
C26 H26 0.93 . ?
C27 C28 1.367(7) . ?
C27 H27 0.93 . ?
C28 C29 1.365(7) . ?
C28 H28 0.93 . ?
C29 C30 1.385(5) . ?
C29 H29 0.93 . ?
C30 H30 0.93 . ?
C31 C36 1.382(5) . ?
C31 C32 1.383(5) . ?
C31 P1 1.799(3) . ?
C32 C33 1.380(5) . ?
C32 H32 0.93 . ?
C33 C34 1.374(6) . ?
C33 H33 0.93 . ?
C34 C35 1.361(6) . ?
C34 H34 0.93 . ?
C35 C36 1.383(6) . ?
C35 H35 0.93 . ?
C36 H36 0.93 . ?
C37A O1 1.431(11) . ?
C37A C38A 1.509(15) . ?
C37A H37A 0.97 . ?
C37A H37B 0.97 . ?
C38A H38A 0.96 . ?
C38A H38B 0.96 . ?
C38A H38C 0.96 . ?
C37B O1 1.244(9) . ?
C37B C38B 1.513(16) . ?
C37B H37C 0.97 . ?
C37B H37D 0.97 . ?
C38B H38D 0.96 . ?
C38B H38E 0.96 . ?
C38B H38F 0.96 . ?
O1 C37B 1.244(9) 2_566 ?
O1 C37A 1.431(12) 2_566 ?

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 C2 119.0(3) . . ?
C6 C1 C7 119.6(3) . . ?
C2 C1 C7 121.3(3) . . ?
C3 C2 C1 118.1(3) . . ?
C3 C2 C10 120.4(3) . . ?
C1 C2 C10 121.5(3) . . ?
C2 C3 C4 121.6(4) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 119.9(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 119.7(4) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 121.7(4) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
C8 C7 C1 116.1(3) . . ?
C8 C7 Se1 109.6(3) . . ?
C1 C7 Se1 111.2(2) . . ?
C8 C7 H7 106.4 . . ?
C1 C7 H7 106.4 . . ?
Se1 C7 H7 106.4 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 Se1 178.8(4) . . ?
C2 C10 C11 116.7(3) . . ?
C2 C10 Se2 110.2(2) . . ?
C11 C10 Se2 109.9(2) . . ?
C2 C10 H10 106.5 . . ?
C11 C10 H10 106.5 . . ?
Se2 C10 H10 106.5 . . ?
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 . . ?
N2 C12 Se2 177.3(4) . . ?
C18 C13 C14 120.4(3) . . ?
C18 C13 P1 121.0(3) . . ?
C14 C13 P1 118.4(3) . . ?
C15 C14 C13 119.8(4) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 119.7(4) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 121.1(4) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C18 120.0(4) . . ?
C16 C17 H17 120 . . ?
C18 C17 H17 120 . . ?
C13 C18 C17 118.9(4) . . ?
C13 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C20 C19 C24 119.9(3) . . ?
C20 C19 P1 119.8(3) . . ?
C24 C19 P1 120.2(2) . . ?
C21 C20 C19 119.2(4) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C22 C21 C20 120.5(4) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C21 120.5(4) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 120.1(4) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 119.8(3) . . ?
C23 C24 H24 120.1 . . ?
C19 C24 H24 120.1 . . ?
C26 C25 C30 119.8(3) . . ?
C26 C25 P1 122.5(3) . . ?
C30 C25 P1 117.8(3) . . ?
C25 C26 C27 119.7(4) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C28 C27 C26 120.3(4) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C29 C28 C27 120.3(4) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C29 C30 120.3(4) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C29 C30 C25 119.6(4) . . ?
C29 C30 H30 120.2 . . ?
C25 C30 H30 120.2 . . ?
C36 C31 C32 119.2(3) . . ?
C36 C31 P1 120.5(3) . . ?
C32 C31 P1 120.0(2) . . ?
C33 C32 C31 120.1(3) . . ?
C33 C32 H32 120 . . ?
C31 C32 H32 120 . . ?
C34 C33 C32 120.6(4) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C35 C34 C33 119.2(3) . . ?
C35 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?
C34 C35 C36 121.2(4) . . ?
C34 C35 H35 119.4 . . ?
C36 C35 H35 119.4 . . ?
C31 C36 C35 119.7(4) . . ?
C31 C36 H36 120.1 . . ?
C35 C36 H36 120.1 . . ?
O1 C37A C38A 117.8(12) . . ?
O1 C37A H37A 107.9 . . ?
C38A C37A H37A 107.9 . . ?
O1 C37A H37B 107.9 . . ?
C38A C37A H37B 107.9 . . ?
H37A C37A H37B 107.2 . . ?
C37A C38A H38A 109.5 . . ?
C37A C38A H38B 109.5 . . ?
H38A C38A H38B 109.5 . . ?
C37A C38A H38C 109.5 . . ?
H38A C38A H38C 109.5 . . ?
H38B C38A H38C 109.5 . . ?
O1 C37B C38B 103.2(11) . . ?
O1 C37B H37C 111.1 . . ?
C38B C37B H37C 111.1 . . ?
O1 C37B H37D 111.1 . . ?
C38B C37B H37D 111.1 . . ?
H37C C37B H37D 109.1 . . ?
C37B C38B H38D 109.5 . . ?
C37B C38B H38E 109.5 . . ?
H38D C38B H38E 109.5 . . ?
C37B C38B H38F 109.5 . . ?
H38D C38B H38F 109.5 . . ?
H38E C38B H38F 109.5 . . ?
C25 P1 C19 108.99(15) . . ?
C25 P1 C31 108.32(14) . . ?
C19 P1 C31 111.32(14) . . ?
C25 P1 C13 108.81(15) . . ?
C19 P1 C13 110.65(15) . . ?
C31 P1 C13 108.70(15) . . ?
C9 Se1 C7 94.52(16) . . ?
C12 Se2 C10 94.98(15) . . ?
C37B O1 C37B 180 . 2_566 ?
C37A O1 C37A 180 . 2_566 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.3(5) . . . . ?
C7 C1 C2 C3 -179.7(3) . . . . ?
C6 C1 C2 C10 178.9(3) . . . . ?
C7 C1 C2 C10 0.5(5) . . . . ?
C1 C2 C3 C4 0.8(5) . . . . ?
C10 C2 C3 C4 -179.4(3) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
C3 C4 C5 C6 -1.2(6) . . . . ?
C4 C5 C6 C1 0.7(6) . . . . ?
C2 C1 C6 C5 0.6(5) . . . . ?
C7 C1 C6 C5 179.0(3) . . . . ?
C6 C1 C7 C8 -20.7(5) . . . . ?
C2 C1 C7 C8 157.6(3) . . . . ?
C6 C1 C7 Se1 105.6(3) . . . . ?
C2 C1 C7 Se1 -76.1(3) . . . . ?
C3 C2 C10 C11 -21.5(5) . . . . ?
C1 C2 C10 C11 158.3(3) . . . . ?
C3 C2 C10 Se2 104.7(3) . . . . ?
C1 C2 C10 Se2 -75.5(3) . . . . ?
C18 C13 C14 C15 -0.4(6) . . . . ?
P1 C13 C14 C15 175.9(3) . . . . ?
C13 C14 C15 C16 1.5(7) . . . . ?
C14 C15 C16 C17 -1.2(8) . . . . ?
C15 C16 C17 C18 -0.3(7) . . . . ?
C14 C13 C18 C17 -1.1(6) . . . . ?
P1 C13 C18 C17 -177.3(3) . . . . ?
C16 C17 C18 C13 1.5(6) . . . . ?
C24 C19 C20 C21 1.4(6) . . . . ?
P1 C19 C20 C21 -177.9(3) . . . . ?
C19 C20 C21 C22 -0.2(7) . . . . ?
C20 C21 C22 C23 -1.2(8) . . . . ?
C21 C22 C23 C24 1.4(7) . . . . ?
C22 C23 C24 C19 -0.2(6) . . . . ?
C20 C19 C24 C23 -1.2(5) . . . . ?
P1 C19 C24 C23 178.1(3) . . . . ?
C30 C25 C26 C27 -1.0(5) . . . . ?
P1 C25 C26 C27 -179.0(3) . . . . ?
C25 C26 C27 C28 1.1(6) . . . . ?
C26 C27 C28 C29 -0.1(7) . . . . ?
C27 C28 C29 C30 -1.0(6) . . . . ?
C28 C29 C30 C25 1.1(6) . . . . ?
C26 C25 C30 C29 -0.1(5) . . . . ?
P1 C25 C30 C29 178.0(3) . . . . ?
C36 C31 C32 C33 1.4(5) . . . . ?
P1 C31 C32 C33 -172.1(3) . . . . ?
C31 C32 C33 C34 -0.1(6) . . . . ?
C32 C33 C34 C35 -0.5(6) . . . . ?
C33 C34 C35 C36 -0.2(7) . . . . ?
C32 C31 C36 C35 -2.0(6) . . . . ?
P1 C31 C36 C35 171.4(3) . . . . ?
C34 C35 C36 C31 1.4(7) . . . . ?
C26 C25 P1 C19 -14.7(3) . . . . ?
C30 C25 P1 C19 167.2(3) . . . . ?
C26 C25 P1 C31 -136.0(3) . . . . ?
C30 C25 P1 C31 46.0(3) . . . . ?
C26 C25 P1 C13 106.0(3) . . . . ?
C30 C25 P1 C13 -72.0(3) . . . . ?
C20 C19 P1 C25 129.4(3) . . . . ?
C24 C19 P1 C25 -49.9(3) . . . . ?
C20 C19 P1 C31 -111.2(3) . . . . ?
C24 C19 P1 C31 69.5(3) . . . . ?
C20 C19 P1 C13 9.8(3) . . . . ?
C24 C19 P1 C13 -169.5(3) . . . . ?
C36 C31 P1 C25 -88.8(3) . . . . ?
C32 C31 P1 C25 84.5(3) . . . . ?
C36 C31 P1 C19 151.4(3) . . . . ?
C32 C31 P1 C19 -35.3(3) . . . . ?
C36 C31 P1 C13 29.2(3) . . . . ?
C32 C31 P1 C13 -157.4(3) . . . . ?
C18 C13 P1 C25 -11.0(3) . . . . ?
C14 C13 P1 C25 172.7(3) . . . . ?
C18 C13 P1 C19 108.7(3) . . . . ?
C14 C13 P1 C19 -67.6(3) . . . . ?
C18 C13 P1 C31 -128.8(3) . . . . ?
C14 C13 P1 C31 55.0(3) . . . . ?

####################################################################### 
# 
# 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_anti-Ph4PBr
_database_code_depnum_ccdc_archive 'CCDC 2040294'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2020-10-23 deposited with the CCDC.	2020-11-24 downloaded from the CCDC.
;

_audit_creation_date             2019-01-24T10:45:24-00:00
_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            'C38 H37 Br N2 O0.50 P Se2'
_chemical_formula_moiety         'C24 H20 P, C12 H12 N2 Se2, 0.5(C4 H10 O), Br'
_chemical_formula_weight         798.49

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

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

_cell_length_a                   9.3752(5)
_cell_length_b                   13.5967(6)
_cell_length_c                   14.3500(7)
_cell_angle_alpha                82.051(2)
_cell_angle_beta                 87.549(2)
_cell_angle_gamma                83.173(2)
_cell_volume                     1798.15(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9872
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      26.51
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             802

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

_exptl_absorpt_coefficient_mu    3.242
_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  0.542
_exptl_absorpt_correction_T_max  0.656

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.5826  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   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      0.084898
_diffrn_orient_matrix_ub_12      0.002781
_diffrn_orient_matrix_ub_13      -0.044515
_diffrn_orient_matrix_ub_21      0.058514
_diffrn_orient_matrix_ub_22      -0.048919
_diffrn_orient_matrix_ub_23      0.04589
_diffrn_orient_matrix_ub_31      -0.03028
_diffrn_orient_matrix_ub_32      -0.05645
_diffrn_orient_matrix_ub_33      -0.029444
_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  0.0298
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_number            29306
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.584
_diffrn_reflns_theta_max         27.522
_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             8249
_reflns_number_gt                5578
_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    'SIR-92 (Altomare et al., 1994)'
_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     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_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)+(0.0259P)²+2.1769P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         8249
_refine_ls_number_parameters     425
_refine_ls_number_restraints     2
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.091
_refine_ls_wR_factor_gt          0.0732
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.898
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.071

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


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
Br Br -0.2901 2.4595 '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 0.6916(4) 0.1358(2) 0.0486(2) 0.0426(8) Uani 1 1 d . . . . .
C2 C 0.5483(3) 0.1606(2) 0.0219(2) 0.0401(7) Uani 1 1 d . . . . .
C3 C 0.5159(4) 0.1508(3) -0.0698(3) 0.0557(9) Uani 1 1 d . . . . .
H3 H 0.4215 0.1666 -0.0892 0.067 Uiso 1 1 calc R U . . .
C4 C 0.6207(5) 0.1180(3) -0.1329(3) 0.0647(11) Uani 1 1 d . . . . .
H4 H 0.5964 0.1106 -0.1935 0.078 Uiso 1 1 calc R U . . .
C5 C 0.7597(5) 0.0965(3) -0.1058(3) 0.0639(11) Uani 1 1 d . . . . .
H5 H 0.8308 0.0763 -0.1485 0.077 Uiso 1 1 calc R U . . .
C6 C 0.7950(4) 0.1047(3) -0.0157(3) 0.0531(9) Uani 1 1 d . . . . .
H6 H 0.89 0.0892 0.0024 0.064 Uiso 1 1 calc R U . . .
C7 C 0.7364(3) 0.1447(2) 0.1478(2) 0.0433(8) Uani 1 1 d . . . . .
H7 H 0.681 0.2054 0.1656 0.052 Uiso 1 1 calc R U . . .
C8 C 0.8931(4) 0.1569(3) 0.1590(3) 0.0637(11) Uani 1 1 d . . . . .
H8A H 0.9521 0.0981 0.1442 0.096 Uiso 1 1 calc R U . . .
H8B H 0.9083 0.1662 0.2228 0.096 Uiso 1 1 calc R U . . .
H8C H 0.9182 0.214 0.1172 0.096 Uiso 1 1 calc R U . . .
C9 C 0.7974(4) -0.0661(3) 0.1867(3) 0.0564(9) Uani 1 1 d . . . . .
C10 C 0.4330(3) 0.1967(2) 0.0885(2) 0.0436(8) Uani 1 1 d . . . . .
H10 H 0.4524 0.1567 0.1498 0.052 Uiso 1 1 calc R U . . .
C11 C 0.2797(4) 0.1851(3) 0.0664(3) 0.0673(11) Uani 1 1 d . . . . .
H11A H 0.2527 0.2276 0.0093 0.101 Uiso 1 1 calc R U . . .
H11B H 0.2166 0.2036 0.1171 0.101 Uiso 1 1 calc R U . . .
H11C H 0.2728 0.1168 0.0588 0.101 Uiso 1 1 calc R U . . .
C12 C 0.4254(4) 0.3896(3) -0.0205(3) 0.0564(10) Uani 1 1 d . . . . .
C13 C 0.8677(3) 0.1596(2) 0.5585(2) 0.0366(7) Uani 1 1 d . . . . .
C14 C 0.7628(4) 0.1350(3) 0.5044(3) 0.0587(10) Uani 1 1 d . . . . .
H14 H 0.73 0.179 0.4522 0.07 Uiso 1 1 calc R U . . .
C15 C 0.7060(5) 0.0454(3) 0.5274(3) 0.0679(11) Uani 1 1 d . . . . .
H15 H 0.6356 0.0292 0.4903 0.082 Uiso 1 1 calc R U . . .
C16 C 0.7520(5) -0.0193(3) 0.6036(3) 0.0657(11) Uani 1 1 d . . . . .
H16 H 0.712 -0.0789 0.6197 0.079 Uiso 1 1 calc R U . . .
C17 C 0.8564(6) 0.0037(3) 0.6558(3) 0.0858(15) Uani 1 1 d . . . . .
H17 H 0.8898 -0.0414 0.7071 0.103 Uiso 1 1 calc R U . . .
C18 C 0.9150(5) 0.0933(3) 0.6345(3) 0.0699(12) Uani 1 1 d . . . . .
H18 H 0.9862 0.1083 0.6717 0.084 Uiso 1 1 calc R U . . .
C19 C 1.0977(3) 0.2787(2) 0.5885(2) 0.0395(7) Uani 1 1 d . . . . .
C20 C 1.2099(4) 0.2096(3) 0.5639(3) 0.0574(10) Uani 1 1 d . . . . .
H20 H 1.1945 0.1646 0.5231 0.069 Uiso 1 1 calc R U . . .
C21 C 1.3430(4) 0.2084(4) 0.6001(3) 0.0736(12) Uani 1 1 d . . . . .
H21 H 1.4183 0.1627 0.5833 0.088 Uiso 1 1 calc R U . . .
C22 C 1.3660(5) 0.2733(4) 0.6603(4) 0.0794(14) Uani 1 1 d . . . . .
H22 H 1.457 0.2717 0.6843 0.095 Uiso 1 1 calc R U . . .
C23 C 1.2565(5) 0.3412(3) 0.6860(3) 0.0704(12) Uani 1 1 d . . . . .
H23 H 1.2731 0.3845 0.7281 0.085 Uiso 1 1 calc R U . . .
C24 C 1.1210(4) 0.3454(3) 0.6494(2) 0.0509(9) Uani 1 1 d . . . . .
H24 H 1.0469 0.3924 0.6655 0.061 Uiso 1 1 calc R U . . .
C25 C 0.7974(3) 0.3649(2) 0.5935(2) 0.0387(7) Uani 1 1 d . . . . .
C26 C 0.7525(4) 0.3336(3) 0.6856(2) 0.0511(9) Uani 1 1 d . . . . .
H26 H 0.787 0.2706 0.7153 0.061 Uiso 1 1 calc R U . . .
C27 C 0.6572(4) 0.3958(3) 0.7325(3) 0.0631(11) Uani 1 1 d . . . . .
H27 H 0.6276 0.3748 0.794 0.076 Uiso 1 1 calc R U . . .
C28 C 0.6062(4) 0.4881(3) 0.6892(3) 0.0676(12) Uani 1 1 d . . . . .
H28 H 0.5418 0.5297 0.7214 0.081 Uiso 1 1 calc R U . . .
C29 C 0.6488(5) 0.5203(3) 0.5984(3) 0.0676(11) Uani 1 1 d . . . . .
H29 H 0.6125 0.5831 0.5692 0.081 Uiso 1 1 calc R U . . .
C30 C 0.7459(4) 0.4589(3) 0.5505(3) 0.0513(9) Uani 1 1 d . . . . .
H30 H 0.7763 0.4809 0.4894 0.062 Uiso 1 1 calc R U . . .
C31 C 0.9346(3) 0.3263(2) 0.4133(2) 0.0377(7) Uani 1 1 d . . . . .
C32 C 0.8087(4) 0.3506(3) 0.3627(2) 0.0470(8) Uani 1 1 d . . . . .
H32 H 0.72 0.3433 0.3928 0.056 Uiso 1 1 calc R U . . .
C33 C 0.8162(5) 0.3857(3) 0.2679(2) 0.0608(10) Uani 1 1 d . . . . .
H33 H 0.7324 0.4018 0.2339 0.073 Uiso 1 1 calc R U . . .
C34 C 0.9472(6) 0.3967(3) 0.2238(3) 0.0748(14) Uani 1 1 d . . . . .
H34 H 0.9518 0.4209 0.16 0.09 Uiso 1 1 calc R U . . .
C35 C 1.0708(5) 0.3723(4) 0.2730(3) 0.0753(13) Uani 1 1 d . . . . .
H35 H 1.159 0.3796 0.2422 0.09 Uiso 1 1 calc R U . . .
C36 C 1.0665(4) 0.3370(3) 0.3678(2) 0.0542(9) Uani 1 1 d . . . . .
H36 H 1.1511 0.3204 0.4009 0.065 Uiso 1 1 calc R U . . .
C37A C 0.8897(13) 0.4490(9) -0.0311(8) 0.082(4) Uani 0.5 1 d D . P A 1
H37A H 0.8342 0.495 -0.0774 0.098 Uiso 0.5 1 calc R U P A 1
H37B H 0.8256 0.4326 0.0222 0.098 Uiso 0.5 1 calc R U P A 1
C38A C 0.936(2) 0.3555(11) -0.0730(13) 0.080(5) Uani 0.5 1 d D . P A 1
H38A H 0.9948 0.3707 -0.1285 0.121 Uiso 0.5 1 calc R U P A 1
H38B H 0.8535 0.3269 -0.0892 0.121 Uiso 0.5 1 calc R U P A 1
H38C H 0.9913 0.3085 -0.0281 0.121 Uiso 0.5 1 calc R U P A 1
C37B C 1.0301(12) 0.4171(7) -0.0309(7) 0.086(3) Uani 0.5 1 d D . P A 2
H37C H 1.0677 0.3654 0.0182 0.103 Uiso 0.5 1 calc R U P A 2
H37D H 1.0997 0.4221 -0.0829 0.103 Uiso 0.5 1 calc R U P A 2
C38B C 0.889(2) 0.3963(14) -0.0628(18) 0.125(10) Uani 0.5 1 d D . P A 2
H38D H 0.8475 0.4529 -0.1044 0.188 Uiso 0.5 1 calc R U P A 2
H38E H 0.8255 0.384 -0.0092 0.188 Uiso 0.5 1 calc R U P A 2
H38F H 0.9024 0.3386 -0.0953 0.188 Uiso 0.5 1 calc R U P A 2
N1 N 0.8705(4) -0.1268(3) 0.1548(3) 0.0792(11) Uani 1 1 d . . . . .
N2 N 0.4104(4) 0.4243(3) -0.0970(3) 0.0788(11) Uani 1 1 d . . . . .
O1 O 1 0.5 0 0.0758(13) Uani 1 2 d DS . P . .
P1 P 0.92543(8) 0.28230(6) 0.53701(5) 0.03336(17) Uani 1 1 d . . . . .
Se1 Se 0.68042(4) 0.03142(3) 0.24118(3) 0.05390(11) Uani 1 1 d . . . . .
Se2 Se 0.44869(4) 0.33914(3) 0.10576(3) 0.04936(10) Uani 1 1 d . . . . .
Br1 Br 0.47958(4) 0.22692(3) 0.33071(2) 0.04998(10) Uani 1 1 d . . . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.379(5) . ?
C1 C2 1.402(5) . ?
C1 C7 1.526(5) . ?
C2 C3 1.391(5) . ?
C2 C10 1.497(5) . ?
C3 C4 1.384(5) . ?
C3 H3 0.93 . ?
C4 C5 1.363(6) . ?
C4 H4 0.93 . ?
C5 C6 1.371(5) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.515(5) . ?
C7 Se1 2.002(3) . ?
C7 H7 0.98 . ?
C8 H8A 0.96 . ?
C8 H8B 0.96 . ?
C8 H8C 0.96 . ?
C9 N1 1.142(5) . ?
C9 Se1 1.855(4) . ?
C10 C11 1.516(5) . ?
C10 Se2 2.009(3) . ?
C10 H10 0.98 . ?
C11 H11A 0.96 . ?
C11 H11B 0.96 . ?
C11 H11C 0.96 . ?
C12 N2 1.141(5) . ?
C12 Se2 1.858(4) . ?
C13 C18 1.369(5) . ?
C13 C14 1.378(5) . ?
C13 P1 1.797(3) . ?
C14 C15 1.380(5) . ?
C14 H14 0.93 . ?
C15 C16 1.357(6) . ?
C15 H15 0.93 . ?
C16 C17 1.348(6) . ?
C16 H16 0.93 . ?
C17 C18 1.385(6) . ?
C17 H17 0.93 . ?
C18 H18 0.93 . ?
C19 C24 1.384(5) . ?
C19 C20 1.392(5) . ?
C19 P1 1.797(3) . ?
C20 C21 1.370(5) . ?
C20 H20 0.93 . ?
C21 C22 1.358(6) . ?
C21 H21 0.93 . ?
C22 C23 1.370(6) . ?
C22 H22 0.93 . ?
C23 C24 1.387(5) . ?
C23 H23 0.93 . ?
C24 H24 0.93 . ?
C25 C30 1.381(5) . ?
C25 C26 1.394(4) . ?
C25 P1 1.791(3) . ?
C26 C27 1.376(5) . ?
C26 H26 0.93 . ?
C27 C28 1.363(6) . ?
C27 H27 0.93 . ?
C28 C29 1.373(6) . ?
C28 H28 0.93 . ?
C29 C30 1.387(5) . ?
C29 H29 0.93 . ?
C30 H30 0.93 . ?
C31 C36 1.387(4) . ?
C31 C32 1.394(4) . ?
C31 P1 1.794(3) . ?
C32 C33 1.380(5) . ?
C32 H32 0.93 . ?
C33 C34 1.372(6) . ?
C33 H33 0.93 . ?
C34 C35 1.366(6) . ?
C34 H34 0.93 . ?
C35 C36 1.379(5) . ?
C35 H35 0.93 . ?
C36 H36 0.93 . ?
C37A O1 1.431(12) . ?
C37A C38A 1.492(16) . ?
C37A H37A 0.97 . ?
C37A H37B 0.97 . ?
C38A H38A 0.96 . ?
C38A H38B 0.96 . ?
C38A H38C 0.96 . ?
C37B O1 1.265(10) . ?
C37B C38B 1.490(17) . ?
C37B H37C 0.97 . ?
C37B H37D 0.97 . ?
C38B H38D 0.96 . ?
C38B H38E 0.96 . ?
C38B H38F 0.96 . ?
O1 C37B 1.265(10) 2_765 ?
O1 C37A 1.431(12) 2_765 ?

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 C2 120.1(3) . . ?
C6 C1 C7 119.0(3) . . ?
C2 C1 C7 120.9(3) . . ?
C3 C2 C1 117.6(3) . . ?
C3 C2 C10 120.4(3) . . ?
C1 C2 C10 122.0(3) . . ?
C4 C3 C2 121.5(4) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 119.7(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.2(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.9(4) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C8 C7 C1 116.3(3) . . ?
C8 C7 Se1 109.5(2) . . ?
C1 C7 Se1 111.6(2) . . ?
C8 C7 H7 106.3 . . ?
C1 C7 H7 106.3 . . ?
Se1 C7 H7 106.3 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 Se1 178.7(4) . . ?
C2 C10 C11 116.8(3) . . ?
C2 C10 Se2 110.5(2) . . ?
C11 C10 Se2 109.9(2) . . ?
C2 C10 H10 106.3 . . ?
C11 C10 H10 106.3 . . ?
Se2 C10 H10 106.3 . . ?
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 . . ?
N2 C12 Se2 177.3(4) . . ?
C18 C13 C14 118.8(3) . . ?
C18 C13 P1 120.9(3) . . ?
C14 C13 P1 120.0(2) . . ?
C13 C14 C15 120.2(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 120.6(4) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 119.3(4) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 121.3(4) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C13 C18 C17 119.7(4) . . ?
C13 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C24 C19 C20 120.0(3) . . ?
C24 C19 P1 121.0(3) . . ?
C20 C19 P1 119.0(3) . . ?
C21 C20 C19 119.5(4) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C22 C21 C20 120.6(4) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 120.6(4) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C24 120.2(4) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C19 C24 C23 119.0(4) . . ?
C19 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C30 C25 C26 119.4(3) . . ?
C30 C25 P1 122.5(3) . . ?
C26 C25 P1 118.1(3) . . ?
C27 C26 C25 120.1(4) . . ?
C27 C26 H26 120 . . ?
C25 C26 H26 120 . . ?
C28 C27 C26 120.1(4) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C27 C28 C29 120.7(4) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 H28 119.6 . . ?
C28 C29 C30 119.9(4) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C25 C30 C29 119.9(4) . . ?
C25 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C36 C31 C32 119.7(3) . . ?
C36 C31 P1 120.3(3) . . ?
C32 C31 P1 120.0(2) . . ?
C33 C32 C31 119.8(3) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C34 C33 C32 120.0(4) . . ?
C34 C33 H33 120 . . ?
C32 C33 H33 120 . . ?
C35 C34 C33 120.4(4) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C34 C35 C36 120.8(4) . . ?
C34 C35 H35 119.6 . . ?
C36 C35 H35 119.6 . . ?
C35 C36 C31 119.3(4) . . ?
C35 C36 H36 120.3 . . ?
C31 C36 H36 120.3 . . ?
O1 C37A C38A 117.0(13) . . ?
O1 C37A H37A 108 . . ?
C38A C37A H37A 108 . . ?
O1 C37A H37B 108 . . ?
C38A C37A H37B 108 . . ?
H37A C37A H37B 107.3 . . ?
C37A C38A H38A 109.5 . . ?
C37A C38A H38B 109.5 . . ?
H38A C38A H38B 109.5 . . ?
C37A C38A H38C 109.5 . . ?
H38A C38A H38C 109.5 . . ?
H38B C38A H38C 109.5 . . ?
O1 C37B C38B 103.0(11) . . ?
O1 C37B H37C 111.2 . . ?
C38B C37B H37C 111.2 . . ?
O1 C37B H37D 111.2 . . ?
C38B C37B H37D 111.2 . . ?
H37C C37B H37D 109.1 . . ?
C37B C38B H38D 109.5 . . ?
C37B C38B H38E 109.5 . . ?
H38D C38B H38E 109.5 . . ?
C37B C38B H38F 109.5 . . ?
H38D C38B H38F 109.5 . . ?
H38E C38B H38F 109.5 . . ?
C37B O1 C37B 180 2_765 . ?
C37A O1 C37A 180.0(6) 2_765 . ?
C25 P1 C31 109.23(15) . . ?
C25 P1 C13 107.76(14) . . ?
C31 P1 C13 111.31(14) . . ?
C25 P1 C19 108.92(15) . . ?
C31 P1 C19 110.58(15) . . ?
C13 P1 C19 108.97(15) . . ?
C9 Se1 C7 94.66(15) . . ?
C12 Se2 C10 95.13(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.2(5) . . . . ?
C7 C1 C2 C3 179.8(3) . . . . ?
C6 C1 C2 C10 -178.7(3) . . . . ?
C7 C1 C2 C10 -0.1(4) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C10 C2 C3 C4 179.7(3) . . . . ?
C2 C3 C4 C5 -1.3(6) . . . . ?
C3 C4 C5 C6 1.8(6) . . . . ?
C4 C5 C6 C1 -0.8(6) . . . . ?
C2 C1 C6 C5 -0.8(5) . . . . ?
C7 C1 C6 C5 -179.4(3) . . . . ?
C6 C1 C7 C8 22.2(4) . . . . ?
C2 C1 C7 C8 -156.4(3) . . . . ?
C6 C1 C7 Se1 -104.4(3) . . . . ?
C2 C1 C7 Se1 77.0(3) . . . . ?
C3 C2 C10 C11 21.9(5) . . . . ?
C1 C2 C10 C11 -158.2(3) . . . . ?
C3 C2 C10 Se2 -104.7(3) . . . . ?
C1 C2 C10 Se2 75.2(3) . . . . ?
C18 C13 C14 C15 0.6(6) . . . . ?
P1 C13 C14 C15 -172.4(3) . . . . ?
C13 C14 C15 C16 0.3(7) . . . . ?
C14 C15 C16 C17 -1.5(7) . . . . ?
C15 C16 C17 C18 1.7(8) . . . . ?
C14 C13 C18 C17 -0.4(6) . . . . ?
P1 C13 C18 C17 172.5(4) . . . . ?
C16 C17 C18 C13 -0.7(8) . . . . ?
C24 C19 C20 C21 -0.2(6) . . . . ?
P1 C19 C20 C21 177.8(3) . . . . ?
C19 C20 C21 C22 0.6(7) . . . . ?
C20 C21 C22 C23 0.0(7) . . . . ?
C21 C22 C23 C24 -1.1(7) . . . . ?
C20 C19 C24 C23 -0.9(5) . . . . ?
P1 C19 C24 C23 -178.7(3) . . . . ?
C22 C23 C24 C19 1.5(6) . . . . ?
C30 C25 C26 C27 0.3(5) . . . . ?
P1 C25 C26 C27 178.3(3) . . . . ?
C25 C26 C27 C28 0.2(6) . . . . ?
C26 C27 C28 C29 0.0(6) . . . . ?
C27 C28 C29 C30 -0.7(6) . . . . ?
C26 C25 C30 C29 -1.0(5) . . . . ?
P1 C25 C30 C29 -178.8(3) . . . . ?
C28 C29 C30 C25 1.2(6) . . . . ?
C36 C31 C32 C33 -0.4(5) . . . . ?
P1 C31 C32 C33 179.2(3) . . . . ?
C31 C32 C33 C34 -0.1(6) . . . . ?
C32 C33 C34 C35 0.6(6) . . . . ?
C33 C34 C35 C36 -0.5(7) . . . . ?
C34 C35 C36 C31 -0.1(6) . . . . ?
C32 C31 C36 C35 0.5(5) . . . . ?
P1 C31 C36 C35 -179.1(3) . . . . ?
C30 C25 P1 C31 -15.0(3) . . . . ?
C26 C25 P1 C31 167.1(3) . . . . ?
C30 C25 P1 C13 -136.0(3) . . . . ?
C26 C25 P1 C13 46.1(3) . . . . ?
C30 C25 P1 C19 105.9(3) . . . . ?
C26 C25 P1 C19 -72.0(3) . . . . ?
C36 C31 P1 C25 130.0(3) . . . . ?
C32 C31 P1 C25 -49.5(3) . . . . ?
C36 C31 P1 C13 -111.1(3) . . . . ?
C32 C31 P1 C13 69.3(3) . . . . ?
C36 C31 P1 C19 10.2(3) . . . . ?
C32 C31 P1 C19 -169.4(3) . . . . ?
C18 C13 P1 C25 -91.8(3) . . . . ?
C14 C13 P1 C25 81.1(3) . . . . ?
C18 C13 P1 C31 148.5(3) . . . . ?
C14 C13 P1 C31 -38.6(3) . . . . ?
C18 C13 P1 C19 26.3(4) . . . . ?
C14 C13 P1 C19 -160.8(3) . . . . ?
C24 C19 P1 C25 -10.2(3) . . . . ?
C20 C19 P1 C25 171.9(3) . . . . ?
C24 C19 P1 C31 109.9(3) . . . . ?
C20 C19 P1 C31 -68.0(3) . . . . ?
C24 C19 P1 C13 -127.5(3) . . . . ?
C20 C19 P1 C13 54.6(3) . . . . ?

####################################################################### 
# 
# 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_anti-Ph4PI
_database_code_depnum_ccdc_archive 'CCDC 2040295'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2020-10-23 deposited with the CCDC.	2020-11-24 downloaded from the CCDC.
;

_audit_creation_date             2019-01-25T15:36:10-00:00
_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            'C36 H32 I N2 P Se2'
_chemical_formula_moiety         'C36 H32 I N2 P Se2'
_chemical_formula_weight         808.42
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.2747(2)
_cell_length_b                   10.6749(2)
_cell_length_c                   34.3002(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3395.94(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9913
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      26.76
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1592

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

_exptl_absorpt_coefficient_mu    3.161
_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  0.691
_exptl_absorpt_correction_T_max  0.777

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.5976  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------# 


#----------------------------------------------------------------------------#
#                   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      -0.088841
_diffrn_orient_matrix_ub_12      -0.03667
_diffrn_orient_matrix_ub_13      -0.011944
_diffrn_orient_matrix_ub_21      -0.041681
_diffrn_orient_matrix_ub_22      0.085899
_diffrn_orient_matrix_ub_23      -0.002876
_diffrn_orient_matrix_ub_31      0.044669
_diffrn_orient_matrix_ub_32      0.007222
_diffrn_orient_matrix_ub_33      -0.026439
_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  0.0247
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_number            24731
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.497
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_coverage         0.774
_reflns_number_total             7781
_reflns_number_gt                6512
_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    'SIR-92 (Altomare et al., 1994)'
_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     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refined as a 2-component inversion 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)+(0.0310P)²+1.2630P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7781
_refine_ls_number_parameters     382
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.07
_refine_ls_wR_factor_gt          0.0671
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_restrained_S_all      1.02
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.640(10)
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.058

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


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
I I -0.4742 1.8119 '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 0.5637(5) 0.5712(4) 0.55143(12) 0.0404(10) Uani 1 1 d . . . . .
C2 C 0.7033(5) 0.6241(4) 0.54853(12) 0.0368(10) Uani 1 1 d . . . . .
C3 C 0.7732(6) 0.6173(5) 0.51260(14) 0.0504(13) Uani 1 1 d . . . . .
H3 H 0.8638 0.6538 0.51 0.06 Uiso 1 1 calc R U . . .
C4 C 0.7129(7) 0.5587(5) 0.48102(14) 0.0616(15) Uani 1 1 d . . . . .
H4 H 0.7627 0.555 0.4575 0.074 Uiso 1 1 calc R U . . .
C5 C 0.5789(7) 0.5056(6) 0.48415(15) 0.0636(16) Uani 1 1 d . . . . .
H5 H 0.5378 0.4652 0.4629 0.076 Uiso 1 1 calc R U . . .
C6 C 0.5055(6) 0.5123(5) 0.51900(15) 0.0548(13) Uani 1 1 d . . . . .
H6 H 0.4144 0.4764 0.5208 0.066 Uiso 1 1 calc R U . . .
C7 C 0.4787(5) 0.5799(4) 0.58874(13) 0.0436(10) Uani 1 1 d . . . . .
H7 H 0.5119 0.6567 0.6016 0.052 Uiso 1 1 calc R U . . .
C8 C 0.3167(6) 0.5958(6) 0.58351(17) 0.0651(15) Uani 1 1 d . . . . .
H8A H 0.2982 0.6666 0.567 0.098 Uiso 1 1 calc R U . . .
H8B H 0.2724 0.6091 0.6085 0.098 Uiso 1 1 calc R U . . .
H8C H 0.2773 0.5217 0.5718 0.098 Uiso 1 1 calc R U . . .
C9 C 0.4536(6) 0.3114(6) 0.59481(16) 0.0559(13) Uani 1 1 d . . . . .
C10 C 0.7744(5) 0.6857(5) 0.58215(13) 0.0424(10) Uani 1 1 d . . . . .
H10 H 0.7566 0.6316 0.6047 0.051 Uiso 1 1 calc R U . . .
C11 C 0.9374(5) 0.7023(7) 0.57968(18) 0.0701(17) Uani 1 1 d . . . . .
H11A H 0.9816 0.6232 0.5737 0.105 Uiso 1 1 calc R U . . .
H11B H 0.9732 0.7324 0.6042 0.105 Uiso 1 1 calc R U . . .
H11C H 0.9601 0.7616 0.5596 0.105 Uiso 1 1 calc R U . . .
C12 C 0.6701(6) 0.9068(5) 0.54386(17) 0.0555(12) Uani 1 1 d . . . . .
C13 C 0.7951(4) 0.1891(4) 0.67936(10) 0.0326(9) Uani 1 1 d . . . . .
C14 C 0.7299(5) 0.0721(5) 0.67746(13) 0.0431(11) Uani 1 1 d . . . . .
H14 H 0.7773 0.0056 0.6655 0.052 Uiso 1 1 calc R U . . .
C15 C 0.5952(5) 0.0548(5) 0.69324(15) 0.0526(13) Uani 1 1 d . . . . .
H15 H 0.551 -0.0232 0.6916 0.063 Uiso 1 1 calc R U . . .
C16 C 0.5263(6) 0.1510(6) 0.71123(16) 0.0615(15) Uani 1 1 d . . . . .
H16 H 0.4356 0.1381 0.722 0.074 Uiso 1 1 calc R U . . .
C17 C 0.5894(6) 0.2674(6) 0.71360(16) 0.0588(14) Uani 1 1 d . . . . .
H17 H 0.5413 0.3325 0.726 0.071 Uiso 1 1 calc R U . . .
C18 C 0.7248(5) 0.2879(5) 0.69749(13) 0.0421(11) Uani 1 1 d . . . . .
H18 H 0.7675 0.3666 0.6988 0.05 Uiso 1 1 calc R U . . .
C19 C 1.0542(4) 0.3450(4) 0.67788(12) 0.0341(9) Uani 1 1 d . . . . .
C20 C 1.1576(5) 0.3262(4) 0.70675(14) 0.0499(12) Uani 1 1 d . . . . .
H20 H 1.1826 0.2455 0.7143 0.06 Uiso 1 1 calc R U . . .
C21 C 1.2225(6) 0.4278(5) 0.72392(17) 0.0617(15) Uani 1 1 d . . . . .
H21 H 1.2923 0.4156 0.743 0.074 Uiso 1 1 calc R U . . .
C22 C 1.1849(6) 0.5475(5) 0.71308(15) 0.0563(13) Uani 1 1 d . . . . .
H22 H 1.2311 0.6159 0.7243 0.068 Uiso 1 1 calc R U . . .
C23 C 1.0802(6) 0.5658(5) 0.68592(17) 0.0594(14) Uani 1 1 d . . . . .
H23 H 1.052 0.6468 0.6795 0.071 Uiso 1 1 calc R U . . .
C24 C 1.0160(6) 0.4656(4) 0.66787(14) 0.0501(12) Uani 1 1 d . . . . .
H24 H 0.9464 0.4791 0.6488 0.06 Uiso 1 1 calc R U . . .
C25 C 1.0741(4) 0.0767(4) 0.66191(12) 0.0330(9) Uani 1 1 d . . . . .
C26 C 1.1710(5) 0.0416(5) 0.63315(14) 0.0500(11) Uani 1 1 d . . . . .
H26 H 1.1749 0.086 0.6098 0.06 Uiso 1 1 calc R U . . .
C27 C 1.2614(6) -0.0586(5) 0.63907(17) 0.0605(15) Uani 1 1 d . . . . .
H27 H 1.3247 -0.0829 0.6194 0.073 Uiso 1 1 calc R U . . .
C28 C 1.2592(6) -0.1232(5) 0.67357(18) 0.0584(15) Uani 1 1 d . . . . .
H28 H 1.3225 -0.1895 0.6776 0.07 Uiso 1 1 calc R U . . .
C29 C 1.1649(7) -0.0901(5) 0.70153(16) 0.0615(14) Uani 1 1 d . . . . .
H29 H 1.162 -0.135 0.7248 0.074 Uiso 1 1 calc R U . . .
C30 C 1.0729(6) 0.0090(5) 0.69621(15) 0.0527(13) Uani 1 1 d . . . . .
H30 H 1.0089 0.0309 0.7159 0.063 Uiso 1 1 calc R U . . .
C31 C 0.9371(4) 0.2473(4) 0.60535(11) 0.0331(9) Uani 1 1 d . . . . .
C32 C 1.0452(5) 0.3060(5) 0.58451(13) 0.0501(12) Uani 1 1 d . . . . .
H32 H 1.1313 0.3278 0.5967 0.06 Uiso 1 1 calc R U . . .
C33 C 1.0241(7) 0.3322(5) 0.54544(14) 0.0619(14) Uani 1 1 d . . . . .
H33 H 1.0964 0.3719 0.5313 0.074 Uiso 1 1 calc R U . . .
C34 C 0.8990(7) 0.3007(5) 0.52769(14) 0.0587(14) Uani 1 1 d . . . . .
H34 H 0.8863 0.3184 0.5014 0.07 Uiso 1 1 calc R U . . .
C35 C 0.7911(6) 0.2428(5) 0.54803(14) 0.0553(14) Uani 1 1 d . . . . .
H35 H 0.7055 0.222 0.5355 0.066 Uiso 1 1 calc R U . . .
C36 C 0.8085(5) 0.2150(4) 0.58733(12) 0.0429(11) Uani 1 1 d . . . . .
H36 H 0.7354 0.1756 0.6013 0.052 Uiso 1 1 calc R U . . .
N1 N 0.4142(6) 0.2287(6) 0.57790(18) 0.0820(16) Uani 1 1 d . . . . .
N2 N 0.6549(7) 0.9420(5) 0.51276(16) 0.0854(16) Uani 1 1 d . . . . .
P1 P 0.96487(11) 0.21373(10) 0.65603(3) 0.0306(2) Uani 1 1 d . . . . .
Se1 Se 0.52250(6) 0.44202(6) 0.62570(2) 0.05613(15) Uani 1 1 d . . . . .
Se2 Se 0.68201(7) 0.85197(5) 0.59462(2) 0.06030(16) Uani 1 1 d . . . . .
I1 I 0.66287(5) 0.68490(4) 0.68799(2) 0.06624(13) 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 1.387(7) . ?
C1 C2 1.416(6) . ?
C1 C7 1.506(6) . ?
C2 C3 1.394(6) . ?
C2 C10 1.482(6) . ?
C3 C4 1.371(8) . ?
C3 H3 0.93 . ?
C4 C5 1.370(8) . ?
C4 H4 0.93 . ?
C5 C6 1.377(8) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.523(7) . ?
C7 Se1 1.985(4) . ?
C7 H7 0.98 . ?
C8 H8A 0.96 . ?
C8 H8B 0.96 . ?
C8 H8C 0.96 . ?
C9 N1 1.118(7) . ?
C9 Se1 1.864(7) . ?
C10 C11 1.525(7) . ?
C10 Se2 2.017(5) . ?
C10 H10 0.98 . ?
C11 H11A 0.96 . ?
C11 H11B 0.96 . ?
C11 H11C 0.96 . ?
C12 N2 1.140(7) . ?
C12 Se2 1.840(6) . ?
C13 C18 1.387(6) . ?
C13 C14 1.389(6) . ?
C13 P1 1.786(4) . ?
C14 C15 1.374(7) . ?
C14 H14 0.93 . ?
C15 C16 1.358(8) . ?
C15 H15 0.93 . ?
C16 C17 1.375(8) . ?
C16 H16 0.93 . ?
C17 C18 1.389(7) . ?
C17 H17 0.93 . ?
C18 H18 0.93 . ?
C19 C24 1.379(6) . ?
C19 C20 1.393(6) . ?
C19 P1 1.792(4) . ?
C20 C21 1.373(7) . ?
C20 H20 0.93 . ?
C21 C22 1.376(8) . ?
C21 H21 0.93 . ?
C22 C23 1.360(7) . ?
C22 H22 0.93 . ?
C23 C24 1.372(7) . ?
C23 H23 0.93 . ?
C24 H24 0.93 . ?
C25 C30 1.381(6) . ?
C25 C26 1.386(6) . ?
C25 P1 1.791(4) . ?
C26 C27 1.375(7) . ?
C26 H26 0.93 . ?
C27 C28 1.370(8) . ?
C27 H27 0.93 . ?
C28 C29 1.345(8) . ?
C28 H28 0.93 . ?
C29 C30 1.372(7) . ?
C29 H29 0.93 . ?
C30 H30 0.93 . ?
C31 C32 1.382(6) . ?
C31 C36 1.387(6) . ?
C31 P1 1.793(4) . ?
C32 C33 1.383(7) . ?
C32 H32 0.93 . ?
C33 C34 1.353(8) . ?
C33 H33 0.93 . ?
C34 C35 1.368(8) . ?
C34 H34 0.93 . ?
C35 C36 1.390(6) . ?
C35 H35 0.93 . ?
C36 H36 0.93 . ?

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 C2 118.7(4) . . ?
C6 C1 C7 120.4(4) . . ?
C2 C1 C7 120.9(4) . . ?
C3 C2 C1 117.8(4) . . ?
C3 C2 C10 120.3(4) . . ?
C1 C2 C10 121.9(4) . . ?
C4 C3 C2 122.2(5) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 119.8(5) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 119.7(5) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 121.8(5) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
C1 C7 C8 115.0(4) . . ?
C1 C7 Se1 113.0(3) . . ?
C8 C7 Se1 111.1(3) . . ?
C1 C7 H7 105.6 . . ?
C8 C7 H7 105.6 . . ?
Se1 C7 H7 105.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 Se1 176.2(6) . . ?
C2 C10 C11 116.7(4) . . ?
C2 C10 Se2 111.5(3) . . ?
C11 C10 Se2 109.3(4) . . ?
C2 C10 H10 106.2 . . ?
C11 C10 H10 106.2 . . ?
Se2 C10 H10 106.2 . . ?
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 . . ?
N2 C12 Se2 176.2(6) . . ?
C18 C13 C14 120.0(4) . . ?
C18 C13 P1 120.2(3) . . ?
C14 C13 P1 119.7(3) . . ?
C15 C14 C13 119.9(5) . . ?
C15 C14 H14 120 . . ?
C13 C14 H14 120 . . ?
C16 C15 C14 120.3(5) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 120.7(5) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C18 120.2(5) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 118.9(5) . . ?
C13 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C24 C19 C20 119.2(4) . . ?
C24 C19 P1 120.5(3) . . ?
C20 C19 P1 120.2(3) . . ?
C21 C20 C19 119.6(5) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.4(5) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 120.0(5) . . ?
C23 C22 H22 120 . . ?
C21 C22 H22 120 . . ?
C22 C23 C24 120.5(5) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C19 120.3(4) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?
C30 C25 C26 118.1(4) . . ?
C30 C25 P1 121.2(3) . . ?
C26 C25 P1 120.5(3) . . ?
C27 C26 C25 120.0(5) . . ?
C27 C26 H26 120 . . ?
C25 C26 H26 120 . . ?
C28 C27 C26 120.7(5) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C29 C28 C27 119.6(5) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C28 C29 C30 120.8(5) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C29 C30 C25 120.8(5) . . ?
C29 C30 H30 119.6 . . ?
C25 C30 H30 119.6 . . ?
C32 C31 C36 120.4(4) . . ?
C32 C31 P1 119.2(3) . . ?
C36 C31 P1 120.4(3) . . ?
C31 C32 C33 119.4(5) . . ?
C31 C32 H32 120.3 . . ?
C33 C32 H32 120.3 . . ?
C34 C33 C32 120.5(5) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C33 C34 C35 120.7(5) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 H34 119.6 . . ?
C34 C35 C36 120.4(5) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C31 C36 C35 118.6(4) . . ?
C31 C36 H36 120.7 . . ?
C35 C36 H36 120.7 . . ?
C13 P1 C25 109.2(2) . . ?
C13 P1 C19 109.62(19) . . ?
C25 P1 C19 109.26(19) . . ?
C13 P1 C31 109.69(18) . . ?
C25 P1 C31 110.69(19) . . ?
C19 P1 C31 108.4(2) . . ?
C9 Se1 C7 97.0(2) . . ?
C12 Se2 C10 96.0(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.9(6) . . . . ?
C7 C1 C2 C3 -177.3(4) . . . . ?
C6 C1 C2 C10 -178.4(4) . . . . ?
C7 C1 C2 C10 2.4(6) . . . . ?
C1 C2 C3 C4 -1.9(7) . . . . ?
C10 C2 C3 C4 178.5(5) . . . . ?
C2 C3 C4 C5 0.7(8) . . . . ?
C3 C4 C5 C6 0.5(9) . . . . ?
C4 C5 C6 C1 -0.3(9) . . . . ?
C2 C1 C6 C5 -0.9(8) . . . . ?
C7 C1 C6 C5 178.3(5) . . . . ?
C6 C1 C7 C8 -34.8(7) . . . . ?
C2 C1 C7 C8 144.4(5) . . . . ?
C6 C1 C7 Se1 94.2(5) . . . . ?
C2 C1 C7 Se1 -86.6(5) . . . . ?
C3 C2 C10 C11 -18.8(7) . . . . ?
C1 C2 C10 C11 161.6(5) . . . . ?
C3 C2 C10 Se2 107.8(4) . . . . ?
C1 C2 C10 Se2 -71.8(5) . . . . ?
C18 C13 C14 C15 0.6(6) . . . . ?
P1 C13 C14 C15 -175.9(4) . . . . ?
C13 C14 C15 C16 -1.0(7) . . . . ?
C14 C15 C16 C17 0.6(8) . . . . ?
C15 C16 C17 C18 0.1(8) . . . . ?
C14 C13 C18 C17 0.2(6) . . . . ?
P1 C13 C18 C17 176.7(4) . . . . ?
C16 C17 C18 C13 -0.5(7) . . . . ?
C24 C19 C20 C21 -1.8(7) . . . . ?
P1 C19 C20 C21 -178.3(4) . . . . ?
C19 C20 C21 C22 0.7(9) . . . . ?
C20 C21 C22 C23 1.7(9) . . . . ?
C21 C22 C23 C24 -3.0(9) . . . . ?
C22 C23 C24 C19 1.8(9) . . . . ?
C20 C19 C24 C23 0.6(8) . . . . ?
P1 C19 C24 C23 177.1(4) . . . . ?
C30 C25 C26 C27 0.6(7) . . . . ?
P1 C25 C26 C27 175.5(4) . . . . ?
C25 C26 C27 C28 -1.4(8) . . . . ?
C26 C27 C28 C29 1.8(9) . . . . ?
C27 C28 C29 C30 -1.3(9) . . . . ?
C28 C29 C30 C25 0.5(9) . . . . ?
C26 C25 C30 C29 -0.1(8) . . . . ?
P1 C25 C30 C29 -175.0(4) . . . . ?
C36 C31 C32 C33 -0.1(7) . . . . ?
P1 C31 C32 C33 -179.9(4) . . . . ?
C31 C32 C33 C34 -0.1(8) . . . . ?
C32 C33 C34 C35 0.3(9) . . . . ?
C33 C34 C35 C36 -0.3(8) . . . . ?
C32 C31 C36 C35 0.1(7) . . . . ?
P1 C31 C36 C35 179.9(4) . . . . ?
C34 C35 C36 C31 0.1(7) . . . . ?
C18 C13 P1 C25 145.3(3) . . . . ?
C14 C13 P1 C25 -38.2(4) . . . . ?
C18 C13 P1 C19 25.7(4) . . . . ?
C14 C13 P1 C19 -157.8(3) . . . . ?
C18 C13 P1 C31 -93.2(4) . . . . ?
C14 C13 P1 C31 83.3(4) . . . . ?
C30 C25 P1 C13 -38.0(4) . . . . ?
C26 C25 P1 C13 147.2(4) . . . . ?
C30 C25 P1 C19 81.8(4) . . . . ?
C26 C25 P1 C19 -92.9(4) . . . . ?
C30 C25 P1 C31 -158.8(4) . . . . ?
C26 C25 P1 C31 26.4(4) . . . . ?
C24 C19 P1 C13 -79.5(4) . . . . ?
C20 C19 P1 C13 96.9(4) . . . . ?
C24 C19 P1 C25 160.9(4) . . . . ?
C20 C19 P1 C25 -22.6(4) . . . . ?
C24 C19 P1 C31 40.2(4) . . . . ?
C20 C19 P1 C31 -143.3(4) . . . . ?
C32 C31 P1 C13 160.3(4) . . . . ?
C36 C31 P1 C13 -19.4(4) . . . . ?
C32 C31 P1 C25 -79.2(4) . . . . ?
C36 C31 P1 C25 101.1(4) . . . . ?
C32 C31 P1 C19 40.7(4) . . . . ?
C36 C31 P1 C19 -139.1(4) . . . . ?

