# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 1557622'
_audit_update_record             
;
2017-06-21 deposited with the CCDC.
2017-07-07 downloaded from the CCDC.
;

_audit_creation_date             2017-02-21T16:35:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_sum            'C20 H16 N4 Se2'
_chemical_formula_moiety         'C10 H8 N2 Se2, C10 H8 N2'
_chemical_formula_weight         470.29

#----------------------------------------------------------------------------#
#                   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                   5.3962(4)
_cell_length_b                   7.7356(6)
_cell_length_c                   11.7477(9)
_cell_angle_alpha                99.421(3)
_cell_angle_beta                 94.558(2)
_cell_angle_gamma                104.661(2)
_cell_volume                     464.25(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4292
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      25.79
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.06

_exptl_crystal_density_diffrn    1.682
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             232

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

_exptl_absorpt_coefficient_mu    3.993
_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  0.259
_exptl_absorpt_correction_T_max  0.787

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.4390  0.7461             #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------#


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

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_source                   'Enraf Nonius FR590'
_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      0.005248
_diffrn_orient_matrix_ub_12      -0.091718
_diffrn_orient_matrix_ub_13      0.050414
_diffrn_orient_matrix_ub_21      0.061161
_diffrn_orient_matrix_ub_22      0.100261
_diffrn_orient_matrix_ub_23      0.06967
_diffrn_orient_matrix_ub_31      -0.183094
_diffrn_orient_matrix_ub_32      -0.007987
_diffrn_orient_matrix_ub_33      0.013095
_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  0.052
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_number            12290
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.773
_diffrn_reflns_theta_max         30.551
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             2832
_reflns_number_gt                2161
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    '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)+(0.0273P)²+0.2465P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2832
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0746
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_restrained_S_all      1.06
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.088

#----------------------------------------------------------------------------#
#                   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 0.1896(5) 1.0418(4) 0.9294(2) 0.0325(5) Uani 1 1 d . . . . .
H1 H 0.3183 1.0714 0.8822 0.039 Uiso 1 1 calc R U . . .
C2 C 0.1055(5) 0.8638(3) 0.9465(2) 0.0277(5) Uani 1 1 d . . . . .
C3 C -0.0852(5) 0.8248(4) 1.0185(2) 0.0334(6) Uani 1 1 d . . . . .
H3 H -0.1433 0.7069 1.0318 0.04 Uiso 1 1 calc R U . . .
C4 C 0.2178(5) 0.7205(4) 0.8884(2) 0.0328(5) Uani 1 1 d . . . . .
H4A H 0.212 0.6292 0.9365 0.039 Uiso 1 1 calc R U . . .
H4B H 0.3976 0.7749 0.8816 0.039 Uiso 1 1 calc R U . . .
C5 C -0.2554(6) 0.4717(4) 0.7880(3) 0.0417(7) Uani 1 1 d . . . . .
C6 C 0.4968(6) 0.7462(5) 0.5463(3) 0.0572(9) Uani 1 1 d . . . . .
H6 H 0.3629 0.646 0.51 0.069 Uiso 1 1 calc R U . . .
C7 C 0.6924(6) 0.8106(5) 0.4830(3) 0.0543(9) Uani 1 1 d . . . . .
H7 H 0.69 0.7525 0.4069 0.065 Uiso 1 1 calc R U . . .
C8 C 0.8919(5) 0.9613(4) 0.5326(2) 0.0328(6) Uani 1 1 d . . . . .
C9 C 0.8841(6) 1.0369(4) 0.6472(2) 0.0427(7) Uani 1 1 d . . . . .
H9 H 1.0141 1.1379 0.6857 0.051 Uiso 1 1 calc R U . . .
C10 C 0.6811(6) 0.9603(4) 0.7032(3) 0.0467(7) Uani 1 1 d . . . . .
H10 H 0.6804 1.0129 0.7802 0.056 Uiso 1 1 calc R U . . .
N1 N -0.4344(6) 0.3936(4) 0.8211(3) 0.0635(8) Uani 1 1 d . . . . .
N2 N 0.4874(4) 0.8178(4) 0.6555(2) 0.0445(6) Uani 1 1 d . . . . .
Se1 Se 0.03277(5) 0.60064(4) 0.73157(2) 0.03822(11) Uani 1 1 d . . . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.378(4) 2_577 ?
C1 C2 1.390(3) . ?
C1 H1 0.93 . ?
C2 C3 1.390(3) . ?
C2 C4 1.490(4) . ?
C3 C1 1.378(4) 2_577 ?
C3 H3 0.93 . ?
C4 Se1 1.982(2) . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C5 N1 1.136(4) . ?
C5 Se1 1.856(3) . ?
C6 N2 1.321(4) . ?
C6 C7 1.377(4) . ?
C6 H6 0.93 . ?
C7 C8 1.378(4) . ?
C7 H7 0.93 . ?
C8 C9 1.385(4) . ?
C8 C8 1.498(5) 2_776 ?
C9 C10 1.377(4) . ?
C9 H9 0.93 . ?
C10 N2 1.321(4) . ?
C10 H10 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
C3 C1 C2 121.0(2) 2_577 . ?
C3 C1 H1 119.5 2_577 . ?
C2 C1 H1 119.5 . . ?
C1 C2 C3 118.0(2) . . ?
C1 C2 C4 120.4(2) . . ?
C3 C2 C4 121.6(2) . . ?
C1 C3 C2 121.0(2) 2_577 . ?
C1 C3 H3 119.5 2_577 . ?
C2 C3 H3 119.5 . . ?
C2 C4 Se1 112.67(17) . . ?
C2 C4 H4A 109.1 . . ?
Se1 C4 H4A 109.1 . . ?
C2 C4 H4B 109.1 . . ?
Se1 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
N1 C5 Se1 178.8(3) . . ?
N2 C6 C7 124.1(3) . . ?
N2 C6 H6 117.9 . . ?
C7 C6 H6 117.9 . . ?
C6 C7 C8 119.9(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C8 C9 116.3(2) . . ?
C7 C8 C8 122.2(3) . 2_776 ?
C9 C8 C8 121.4(3) . 2_776 ?
C10 C9 C8 119.1(3) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
N2 C10 C9 124.8(3) . . ?
N2 C10 H10 117.6 . . ?
C9 C10 H10 117.6 . . ?
C10 N2 C6 115.7(3) . . ?
C5 Se1 C4 94.13(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
C3 C1 C2 C3 -0.6(4) 2_577 . . . ?
C3 C1 C2 C4 179.2(2) 2_577 . . . ?
C1 C2 C3 C1 0.6(4) . . . 2_577 ?
C4 C2 C3 C1 -179.2(2) . . . 2_577 ?
C1 C2 C4 Se1 -88.3(3) . . . . ?
C3 C2 C4 Se1 91.5(3) . . . . ?
N2 C6 C7 C8 -1.4(6) . . . . ?
C6 C7 C8 C9 1.6(5) . . . . ?
C6 C7 C8 C8 -179.3(3) . . . 2_776 ?
C7 C8 C9 C10 -0.7(4) . . . . ?
C8 C8 C9 C10 -179.9(3) 2_776 . . . ?
C8 C9 C10 N2 -0.4(5) . . . . ?
C9 C10 N2 C6 0.6(5) . . . . ?
C7 C6 N2 C10 0.3(5) . . . . ?


# END of CIF
_chemical_name_systematic        
"1,4-bis(selenocyanatomethyl)benzene, 4,4'-bipyridine"
####################################################################### 
# 
# 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 1557621'
_audit_update_record             
;
2017-06-21 deposited with the CCDC.
2017-07-07 downloaded from the CCDC.
;

_audit_creation_date             2017-02-17T09:48:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_sum            'C20 H16 N4 Se2'
_chemical_formula_moiety         'C10 H8 N2 Se2, C10 H8 N2'
_chemical_formula_weight         470.29

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   5.1880(5)
_cell_length_b                   14.9962(13)
_cell_length_c                   25.101(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.613(3)
_cell_angle_gamma                90
_cell_volume                     1950.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4890
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      30.04
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04

_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928

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

_exptl_absorpt_coefficient_mu    3.801
_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  0.701
_exptl_absorpt_correction_T_max  0.859

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.5765  0.7461                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------#

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

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      298(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      -0.089557
_diffrn_orient_matrix_ub_12      -0.050387
_diffrn_orient_matrix_ub_13      0.01757
_diffrn_orient_matrix_ub_21      0.167438
_diffrn_orient_matrix_ub_22      -0.018886
_diffrn_orient_matrix_ub_23      0.017848
_diffrn_orient_matrix_ub_31      -0.034286
_diffrn_orient_matrix_ub_32      0.039385
_diffrn_orient_matrix_ub_33      0.031036
_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  0.0378
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_number            20665
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.716
_diffrn_reflns_theta_max         30.579
_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             3010
_reflns_number_gt                2147
_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)+(0.0378P)²+1.5502P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3010
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.037
_refine_ls_wR_factor_ref         0.0877
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_restrained_S_all      1.03
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.062

#----------------------------------------------------------------------------#
#                   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 1 0.2888(2) 0.75 0.0373(6) Uani 1 2 d S T P . .
H1 H 1 0.2268 0.75 0.045 Uiso 1 2 calc R U P . .
C2 C 0.8360(4) 0.33385(15) 0.78285(8) 0.0395(5) Uani 1 1 d . . . . .
C3 C 0.8392(6) 0.42643(18) 0.78251(10) 0.0582(7) Uani 1 1 d . . . . .
H3 H 0.7317 0.4579 0.8044 0.07 Uiso 1 1 calc R U . . .
C4 C 1 0.4718(3) 0.75 0.0698(12) Uani 1 2 d S T P . .
H4 H 1 0.5338 0.75 0.084 Uiso 1 2 calc R U P . .
C5 C 0.6606(5) 0.28417(18) 0.81765(9) 0.0445(5) Uani 1 1 d . . . . .
H5A H 0.6116 0.2283 0.8005 0.053 Uiso 1 1 calc R U . . .
H5B H 0.5048 0.3188 0.8216 0.053 Uiso 1 1 calc R U . . .
C6 C 1.0525(5) 0.17682(18) 0.86296(10) 0.0529(6) Uani 1 1 d . . . . .
C7 C 0.4032(7) 0.3597(3) 0.97423(12) 0.0808(10) Uani 1 1 d . . . . .
H7 H 0.4919 0.3115 0.9895 0.097 Uiso 1 1 calc R U . . .
C8 C 0.2295(6) 0.4040(3) 1.00472(11) 0.0800(11) Uani 1 1 d . . . . .
H8 H 0.2045 0.3852 1.0394 0.096 Uiso 1 1 calc R U . . .
C9 C 0.0942(4) 0.47501(17) 0.98439(9) 0.0451(5) Uani 1 1 d . . . . .
C10 C 0.1386(6) 0.49713(19) 0.93209(12) 0.0654(8) Uani 1 1 d . . . . .
H10 H 0.0494 0.5441 0.9155 0.079 Uiso 1 1 calc R U . . .
C11 C 0.3165(6) 0.4488(2) 0.90480(12) 0.0709(9) Uani 1 1 d . . . . .
H11 H 0.3433 0.465 0.8697 0.085 Uiso 1 1 calc R U . . .
N1 N 1.1971(5) 0.12765(18) 0.84769(11) 0.0748(7) Uani 1 1 d . . . . .
N2 N 0.4512(4) 0.38127(16) 0.92495(9) 0.0581(6) Uani 1 1 d . . . . .
Se1 Se 0.82071(5) 0.25880(2) 0.88924(2) 0.04785(11) Uani 1 1 d . . . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.387(3) . ?
C1 C2 1.387(3) 2_756 ?
C1 H1 0.93 . ?
C2 C3 1.389(3) . ?
C2 C5 1.490(3) . ?
C3 C4 1.373(3) . ?
C3 H3 0.93 . ?
C4 C3 1.373(3) 2_756 ?
C4 H4 0.93 . ?
C5 Se1 1.982(2) . ?
C5 H5A 0.97 . ?
C5 H5B 0.97 . ?
C6 N1 1.131(3) . ?
C6 Se1 1.861(3) . ?
C7 N2 1.313(4) . ?
C7 C8 1.379(4) . ?
C7 H7 0.93 . ?
C8 C9 1.362(4) . ?
C8 H8 0.93 . ?
C9 C10 1.383(3) . ?
C9 C9 1.484(4) 5_567 ?
C10 C11 1.380(4) . ?
C10 H10 0.93 . ?
C11 N2 1.318(4) . ?
C11 H11 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
C2 C1 C2 121.7(3) . 2_756 ?
C2 C1 H1 119.1 . . ?
C2 C1 H1 119.1 2_756 . ?
C1 C2 C3 118.4(2) . . ?
C1 C2 C5 120.9(2) . . ?
C3 C2 C5 120.8(2) . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C3 120.7(4) 2_756 . ?
C3 C4 H4 119.7 2_756 . ?
C3 C4 H4 119.7 . . ?
C2 C5 Se1 112.68(16) . . ?
C2 C5 H5A 109.1 . . ?
Se1 C5 H5A 109.1 . . ?
C2 C5 H5B 109.1 . . ?
Se1 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
N1 C6 Se1 178.6(3) . . ?
N2 C7 C8 124.1(3) . . ?
N2 C7 H7 117.9 . . ?
C8 C7 H7 117.9 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 116.0(2) . . ?
C8 C9 C9 122.5(3) . 5_567 ?
C10 C9 C9 121.5(3) . 5_567 ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N2 C11 C10 124.6(3) . . ?
N2 C11 H11 117.7 . . ?
C10 C11 H11 117.7 . . ?
C7 N2 C11 115.5(2) . . ?
C6 Se1 C5 93.24(11) . . ?

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
C2 C1 C2 C3 -0.25(17) 2_756 . . . ?
C2 C1 C2 C5 179.7(2) 2_756 . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C5 C2 C3 C4 -179.5(2) . . . . ?
C2 C3 C4 C3 -0.25(18) . . . 2_756 ?
C1 C2 C5 Se1 90.3(2) . . . . ?
C3 C2 C5 Se1 -89.7(3) . . . . ?
N2 C7 C8 C9 0.0(6) . . . . ?
C7 C8 C9 C10 1.5(5) . . . . ?
C7 C8 C9 C9 -179.8(3) . . . 5_567 ?
C8 C9 C10 C11 -1.5(4) . . . . ?
C9 C9 C10 C11 179.8(3) 5_567 . . . ?
C9 C10 C11 N2 0.2(5) . . . . ?
C8 C7 N2 C11 -1.4(5) . . . . ?
C10 C11 N2 C7 1.3(5) . . . . ?


# END of CIF
_chemical_name_systematic        
"1,3-bis(selenocyanatomethyl)benzene, 4,4'-bipyridine"
####################################################################### 
# 
# 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 1557620'
_audit_update_record             
;
2017-06-21 deposited with the CCDC.
2017-07-07 downloaded from the CCDC.
;

_audit_creation_date             2017-03-27T15:16:06-00:00
_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 H8 N2 Se2'
_chemical_formula_moiety         'C10 H8 N2 Se2'
_chemical_formula_weight         314.10

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C c'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_Int_Tables_number      9
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   5.9696(7)
_cell_length_b                   36.720(4)
_cell_length_c                   10.2124(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.401(6)
_cell_angle_gamma                90
_cell_volume                     2228.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1633
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.36
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.872
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200

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

_exptl_absorpt_coefficient_mu    6.597
_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  0.854
_exptl_absorpt_correction_T_max  0.936

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.4929  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      0.026569
_diffrn_orient_matrix_ub_12      0.01309
_diffrn_orient_matrix_ub_13      0.085925
_diffrn_orient_matrix_ub_21      0.068386
_diffrn_orient_matrix_ub_22      -0.022542
_diffrn_orient_matrix_ub_23      0.041643
_diffrn_orient_matrix_ub_31      0.151426
_diffrn_orient_matrix_ub_32      0.007884
_diffrn_orient_matrix_ub_33      -0.023596
_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  0.0507
_diffrn_reflns_av_unetI/netI     0.1176
_diffrn_reflns_number            7542
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.109
_diffrn_reflns_theta_max         27.686
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.792
_diffrn_reflns_point_group_measured_fraction_max 0.737
_reflns_Friedel_fraction_full    0.589
_reflns_Friedel_fraction_max     0.5
_reflns_Friedel_coverage         0.51
_reflns_number_total             3849
_reflns_number_gt                2328
_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)+(0.0328P)²+3.2674P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3849
_refine_ls_number_parameters     253
_refine_ls_number_restraints     8
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1
_refine_ls_wR_factor_gt          0.087
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 639 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.401(16)
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.125

#----------------------------------------------------------------------------#
#                   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 0.629(2) 0.1573(4) -0.1574(13) 0.037(3) Uani 1 1 d . . . . .
C2 C 0.624(2) 0.1899(4) -0.2302(13) 0.042(4) Uani 1 1 d . . . . .
H2 H 0.5144 0.2072 -0.2173 0.05 Uiso 1 1 calc R U . . .
C3 C 0.777(2) 0.1971(3) -0.3197(12) 0.033(3) Uani 1 1 d . . . . .
C4 C 0.939(2) 0.1711(4) -0.3345(13) 0.040(4) Uani 1 1 d . . . . .
H4 H 1.0467 0.1759 -0.3924 0.048 Uiso 1 1 calc R U . . .
C5 C 0.951(2) 0.1388(4) -0.2691(13) 0.045(4) Uani 1 1 d . . . . .
H5 H 1.0596 0.1215 -0.2848 0.054 Uiso 1 1 calc R U . . .
C6 C 0.795(2) 0.1322(3) -0.1770(12) 0.033(3) Uani 1 1 d . . . . .
H6 H 0.803 0.1107 -0.1287 0.039 Uiso 1 1 calc R U . . .
C7 C 0.465(2) 0.1503(4) -0.0585(14) 0.059(4) Uani 1 1 d . . . . .
H7A H 0.4502 0.1242 -0.0474 0.07 Uiso 1 1 calc R U . . .
H7B H 0.3186 0.1596 -0.0924 0.07 Uiso 1 1 calc R U . . .
C8 C 0.778(2) 0.2321(4) -0.3885(14) 0.049(4) Uani 1 1 d . . . . .
H8A H 0.9271 0.2428 -0.3728 0.059 Uiso 1 1 calc R U . . .
H8B H 0.673 0.2484 -0.3515 0.059 Uiso 1 1 calc R U . . .
C9 C 0.858(3) 0.1743(4) 0.1075(14) 0.046(4) Uani 1 1 d . . . . .
C10 C 0.391(3) 0.2277(4) -0.5694(16) 0.053(4) Uani 1 1 d . . . . .
C11 C 0.029(2) 0.0813(5) 0.3919(14) 0.061(4) Uani 1 1 d . U . . .
C12 C 0.144(2) 0.0540(4) 0.4685(14) 0.037(3) Uani 1 1 d . . . . .
H12 H 0.0845 0.0306 0.4712 0.045 Uiso 1 1 calc R U . . .
C13 C 0.348(2) 0.0625(4) 0.5407(12) 0.035(3) Uani 1 1 d . . . . .
C14 C 0.433(2) 0.0973(4) 0.5338(14) 0.043(4) Uani 1 1 d . . . . .
H14 H 0.5703 0.1032 0.5797 0.051 Uiso 1 1 calc R U . . .
C15 C 0.319(3) 0.1221(4) 0.4619(15) 0.056(5) Uani 1 1 d . . . . .
H15 H 0.3792 0.1455 0.4617 0.067 Uiso 1 1 calc R U . . .
C16 C 0.122(4) 0.1163(4) 0.3883(16) 0.067(5) Uani 1 1 d . . . . .
H16 H 0.051 0.1347 0.3375 0.08 Uiso 1 1 calc R U . . .
C17 C -0.187(2) 0.0707(5) 0.3128(13) 0.066(4) Uani 1 1 d . U . . .
H17A H -0.2946 0.0905 0.3171 0.079 Uiso 1 1 calc R U . . .
H17B H -0.2492 0.0495 0.3531 0.079 Uiso 1 1 calc R U . . .
C18 C 0.472(2) 0.0328(4) 0.6204(13) 0.050(4) Uani 1 1 d . . . . .
H18A H 0.6287 0.0329 0.6015 0.06 Uiso 1 1 calc R U . . .
H18B H 0.4087 0.0095 0.5925 0.06 Uiso 1 1 calc R U . . .
C19 C 0.152(3) 0.0611(4) 0.1345(14) 0.049(4) Uani 1 1 d . . . . .
C20 C 0.147(3) 0.0368(4) 0.8052(15) 0.045(4) Uani 1 1 d . . . . .
N1 N 1.045(4) 0.1760(4) 0.1026(19) 0.071(4) Uani 1 1 d . . . . .
N2 N 0.204(4) 0.2255(4) -0.573(2) 0.078(5) Uani 1 1 d . . . . .
N3 N 0.347(4) 0.0623(4) 0.125(2) 0.077(5) Uani 1 1 d . . . . .
N4 N -0.036(4) 0.0368(4) 0.801(2) 0.062(4) Uani 1 1 d . . . . .
Se1 Se 0.5505(2) 0.17277(4) 0.11724(14) 0.0440(4) Uani 1 1 d . . . . .
Se2 Se 0.6983(2) 0.22856(4) -0.58072(15) 0.0487(4) Uani 1 1 d . . . . .
Se3 Se -0.1564(2) 0.05974(4) 0.12627(13) 0.0452(4) Uani 1 1 d . . . . .
Se4 Se 0.4606(2) 0.03771(4) 0.81153(13) 0.0437(4) Uani 1 1 d . . . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.383(18) . ?
C1 C2 1.407(18) . ?
C1 C7 1.493(18) . ?
C2 C3 1.375(17) . ?
C2 H2 0.93 . ?
C3 C4 1.380(17) . ?
C3 C8 1.467(17) . ?
C4 C5 1.358(17) . ?
C4 H4 0.93 . ?
C5 C6 1.408(18) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 Se1 1.997(14) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 Se2 1.981(14) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 N1 1.12(3) . ?
C9 Se1 1.851(16) . ?
C10 N2 1.11(3) . ?
C10 Se2 1.851(18) . ?
C11 C16 1.40(2) . ?
C11 C12 1.41(2) . ?
C11 C17 1.506(19) . ?
C12 C13 1.402(19) . ?
C12 H12 0.93 . ?
C13 C14 1.377(17) . ?
C13 C18 1.513(18) . ?
C14 C15 1.32(2) . ?
C14 H14 0.93 . ?
C15 C16 1.35(2) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?
C17 Se3 1.973(14) . ?
C17 H17A 0.97 . ?
C17 H17B 0.97 . ?
C18 Se4 1.968(14) . ?
C18 H18A 0.97 . ?
C18 H18B 0.97 . ?
C19 N3 1.18(3) . ?
C19 Se3 1.834(16) . ?
C20 N4 1.09(3) . ?
C20 Se4 1.867(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.0(12) . . ?
C6 C1 C7 120.4(14) . . ?
C2 C1 C7 121.6(13) . . ?
C3 C2 C1 122.2(13) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C2 C3 C4 117.2(13) . . ?
C2 C3 C8 121.3(13) . . ?
C4 C3 C8 121.2(12) . . ?
C5 C4 C3 123.7(13) . . ?
C5 C4 H4 118.2 . . ?
C3 C4 H4 118.2 . . ?
C4 C5 C6 118.1(13) . . ?
C4 C5 H5 121 . . ?
C6 C5 H5 121 . . ?
C1 C6 C5 120.8(13) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C1 C7 Se1 114.1(10) . . ?
C1 C7 H7A 108.7 . . ?
Se1 C7 H7A 108.7 . . ?
C1 C7 H7B 108.7 . . ?
Se1 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C3 C8 Se2 113.9(9) . . ?
C3 C8 H8A 108.8 . . ?
Se2 C8 H8A 108.8 . . ?
C3 C8 H8B 108.8 . . ?
Se2 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
N1 C9 Se1 178.4(16) . . ?
N2 C10 Se2 174(2) . . ?
C16 C11 C12 119.4(15) . . ?
C16 C11 C17 122.9(17) . . ?
C12 C11 C17 117.6(17) . . ?
C13 C12 C11 119.2(15) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 119.2(14) . . ?
C14 C13 C18 122.2(13) . . ?
C12 C13 C18 118.6(13) . . ?
C15 C14 C13 119.7(15) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 125.1(17) . . ?
C14 C15 H15 117.4 . . ?
C16 C15 H15 117.4 . . ?
C15 C16 C11 117.3(15) . . ?
C15 C16 H16 121.4 . . ?
C11 C16 H16 121.4 . . ?
C11 C17 Se3 114.6(10) . . ?
C11 C17 H17A 108.6 . . ?
Se3 C17 H17A 108.6 . . ?
C11 C17 H17B 108.6 . . ?
Se3 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C13 C18 Se4 114.0(9) . . ?
C13 C18 H18A 108.8 . . ?
Se4 C18 H18A 108.8 . . ?
C13 C18 H18B 108.8 . . ?
Se4 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
N3 C19 Se3 172.7(17) . . ?
N4 C20 Se4 178.8(15) . . ?
C9 Se1 C7 97.8(6) . . ?
C10 Se2 C8 95.0(6) . . ?
C19 Se3 C17 97.8(6) . . ?
C20 Se4 C18 95.4(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 0.7(19) . . . . ?
C7 C1 C2 C3 178.7(13) . . . . ?
C1 C2 C3 C4 -1(2) . . . . ?
C1 C2 C3 C8 -176.1(12) . . . . ?
C2 C3 C4 C5 2(2) . . . . ?
C8 C3 C4 C5 177.2(13) . . . . ?
C3 C4 C5 C6 -3(2) . . . . ?
C2 C1 C6 C5 -1.4(19) . . . . ?
C7 C1 C6 C5 -179.3(13) . . . . ?
C4 C5 C6 C1 2(2) . . . . ?
C6 C1 C7 Se1 95.3(14) . . . . ?
C2 C1 C7 Se1 -82.7(15) . . . . ?
C2 C3 C8 Se2 -114.4(12) . . . . ?
C4 C3 C8 Se2 70.8(15) . . . . ?
C16 C11 C12 C13 1(2) . . . . ?
C17 C11 C12 C13 178.3(12) . . . . ?
C11 C12 C13 C14 -0.7(19) . . . . ?
C11 C12 C13 C18 -178.8(12) . . . . ?
C12 C13 C14 C15 1(2) . . . . ?
C18 C13 C14 C15 179.4(13) . . . . ?
C13 C14 C15 C16 -2(2) . . . . ?
C14 C15 C16 C11 2(2) . . . . ?
C12 C11 C16 C15 -1(2) . . . . ?
C17 C11 C16 C15 -178.7(13) . . . . ?
C16 C11 C17 Se3 79.6(17) . . . . ?
C12 C11 C17 Se3 -98.0(15) . . . . ?
C14 C13 C18 Se4 74.8(15) . . . . ?
C12 C13 C18 Se4 -107.1(13) . . . . ?


# END of CIF
_chemical_name_systematic        1,3-bis(selenocyanatomethyl)benzene
