# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_Se
_database_code_depnum_ccdc_archive 'CCDC 1512478'
_audit_update_record             
;
2017-06-19 deposited with the CCDC.
2017-06-20 downloaded from the CCDC.
;
# Shelxl code: rb16081
_audit_creation_date             2016-10-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            'Grey selenium'
_chemical_name_systematic        Selenium
_chemical_formula_moiety         Se
_chemical_formula_sum            Se
_chemical_formula_weight         78.96
_chemical_absolute_configuration unk
_chemical_melting_point          494
_chemical_oxdiff_formula         Se
_chemical_oxdiff_usercomment     
'Clumps of black needles from "3x sublimed 5tBu Se diradical" sealed tube'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           152
_space_group_name_H-M_alt        'P 31 2 1'
_space_group_name_Hall           'P 31 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'y, x, -z'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'

_cell_length_a                   4.3125(3)
_cell_length_b                   4.3125(3)
_cell_length_c                   4.9711(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     80.064(11)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    757
_cell_measurement_temperature    99.99(14)
_cell_measurement_theta_max      75.6520
_cell_measurement_theta_min      11.8060
_exptl_absorpt_coefficient_mu    39.344
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Black
_exptl_crystal_density_diffrn    4.913
_exptl_crystal_description       Needle
_exptl_crystal_F_000             102
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_diffrn_reflns_av_R_equivalents  0.0911
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            1066
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.668
_diffrn_reflns_theta_min         11.913
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200/300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -1.00  74.00   0.50    0.50    --    4.52  19.00  90.00  150
  2  ω      1.00  71.00   0.50    0.50    --    4.52  38.00-180.00  140
  3  ω     36.00 175.00   0.50    0.91    --  105.46   0.00  90.00  278
  4  ω     97.00 174.00   0.50    0.91    --  105.46  15.00-180.00  154
  5  ω     41.00 110.00   0.50    0.91    --  105.46 -45.00 -90.00  138
  6  ω      1.00  71.00   0.50    0.50    --    4.52  38.00-120.00  140
  7  ω     -1.00  74.00   0.50    0.50    --    4.52  19.00   0.00  150
  8  ω     37.00 109.00   0.50    0.91    --  105.46 -94.00-180.00  144
  9  ω     43.00 119.00   0.50    0.91    --  105.46 -61.00   0.00  152
 10  ω     37.00 109.00   0.50    0.91    --  105.46 -30.00-150.00  144
 11  ω     92.00 168.00   0.50    0.91    --  105.46  61.00 -90.00  152
 12  ω    -45.00  14.00   0.50    0.50    --   -4.52 106.00  40.00  118
 13  ω    -28.00  28.00   0.50    0.50    --    4.52  92.00 144.00  112
 14  ω     97.00 174.00   0.50    0.91    --  105.46  15.00-120.00  154
 15  ω     40.00 122.00   0.50    0.91    --  105.46-125.00  90.00  164
 16  ω    101.00 170.00   0.50    0.91    --  105.46  45.00 120.00  138
 17  ω    102.00 174.00   0.50    0.91    --  105.46  30.00 -60.00  144
 18  ω    -68.00   7.00   0.50    0.50    --   -4.52 -57.00-150.00  150
 19  ω      1.00  71.00   0.50    0.50    --    4.52  36.00  19.00  140
 20  ω     92.00 168.00   0.50    0.91    --  105.46  61.00 -30.00  152
 21  ω     82.00 170.00   0.50    0.91    --  105.46  77.00-150.00  176
 22  ω     97.00 174.00   0.50    0.91    --  105.46  15.00  30.00  154
 23  ω     43.00 119.00   0.50    0.91    --  105.46 -61.00-180.00  152
 24  ω    -25.00  29.00   0.50    0.50    --    4.52 -79.00 -79.00  108
 25  ω    -62.00   8.00   0.50    0.50    --    4.52 -38.00 -60.00  140
 26  ω     82.00 170.00   0.50    0.91    --  105.46  77.00 150.00  176
 27  ω    102.00 174.00   0.50    0.91    --  105.46  30.00  90.00  144
 28  ω     92.00 168.00   0.50    0.91    --  105.46  61.00-120.00  152
 29  ω     40.00 122.00   0.50    0.91    --  105.46-125.00-150.00  164
 30  ω    -64.00  10.00   0.50    0.50    --    4.52 -19.00 120.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Pilatus 200/300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0956512000
_diffrn_orient_matrix_UB_12      0.3951188000
_diffrn_orient_matrix_UB_13      -0.0125151000
_diffrn_orient_matrix_UB_21      -0.1614171000
_diffrn_orient_matrix_UB_22      -0.0611764000
_diffrn_orient_matrix_UB_23      -0.2847260000
_diffrn_orient_matrix_UB_31      -0.3670447000
_diffrn_orient_matrix_UB_32      -0.1018102000
_diffrn_orient_matrix_UB_33      0.1220775000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.481
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                120
_reflns_number_total             120
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.423
_refine_diff_density_min         -1.183
_refine_diff_density_rms         0.365
_refine_ls_abs_structure_Flack   .
_refine_ls_extinction_coef       0.018(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.381
_refine_ls_hydrogen_treatment    .
_refine_ls_matrix_type           full
_refine_ls_number_parameters     7
_refine_ls_number_reflns         120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.381
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0711P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1090
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   .
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 1.0000 0.2287(3) 0.6667 0.0156(9) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 Se1 2.3801(15) 2_645 ?
Se1 Se1 2.3801(15) 3_764 ?

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
Se1 Se1 Se1 103.12(5) 2_645 3_764 ?

# start Validation Reply Form
_vrf_PLAT031_4                   
;
PROBLEM: Refined Extinction Parameter within Range ......      1.800 Sigma 
RESPONSE: Refinement of the extinction parameter was found to be necessary to
achieve convergence. This may be a consequence of the high absorption of using
Cu radiation with Se. However, use of a Mo microsource was unsucessful and it
was found necessary to turn to Cu to solve the structure. Note that the crystal
is a very thin needle, so that the absorption path for many reflections through
the crystal is indeed very short.
;
# end Validation Reply Form 

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.982
_oxdiff_exptl_absorpt_empirical_full_min 0.611
_exptl_crystal_recrystallization_method Sublimation
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1512475'
_audit_update_record             
;
2017-06-19 deposited with the CCDC.
2017-06-20 downloaded from the CCDC.
;
# Shelx code: rb16045
_audit_creation_date             2016-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        
4-[3-(trifluoromethyl)phenyl]-3H-1,2,3,5-Dithiadiazol-3-yl
_chemical_formula_moiety         'C8 H4 F3 N2 S2'
_chemical_formula_sum            'C8 H4 F3 N2 S2'
_chemical_formula_weight         249.25
_chemical_melting_point          415
_chemical_oxdiff_formula         'C8 H4 F3 N2 S2'
_chemical_oxdiff_usercomment     'From a mp capillary labelled m-CF3 dimer'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.12511(16)
_cell_length_b                   16.8803(4)
_cell_length_c                   24.7194(5)
_cell_angle_alpha                108.455(2)
_cell_angle_beta                 91.6884(17)
_cell_angle_gamma                98.597(2)
_cell_volume                     2779.16(12)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    19598
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      77.3510
_cell_measurement_theta_min      5.4110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.398
_exptl_absorpt_correction_T_max  0.857
_exptl_absorpt_correction_T_min  0.625
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic violet'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1500
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 1 0.0581
0 -1 -1 0.0841
-1 1 0 0.1015
1 -1 0 0.1015
2 -2 -5 0.1029
1 1 5 0.0870
0 1 -1 0.0313
0 -1 1 0.0313

_exptl_crystal_preparation       'Previously published.'
_exptl_crystal_recrystallization_method Sublimation
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.063
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0004 1.0001 0.9935 -0.0895 -0.0986 0.0151
0.0004 -1.0001 -0.9935 0.0895 0.0986 -0.0151
-0.9997 0.9997 -0.0020 -0.0696 -0.0383 -0.2101
0.9997 -0.9997 0.0020 0.0696 0.0383 0.2101
2.0001 -2.0001 -4.9868 0.1303 0.4037 0.3849
0.9985 1.0010 4.9835 -0.1040 -0.3551 0.2614
-0.0001 0.9999 -1.0028 -0.0931 0.0322 0.0010
0.0001 -0.9999 1.0028 0.0931 -0.0322 -0.0010

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            51041
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         77.626
_diffrn_reflns_theta_min         3.783
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200/300K'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -33.00   0.50    0.75    --  -38.50 -19.00 150.00  150
  2  ω    -50.00  25.00   0.50    0.75    --  -38.50  57.00  30.00  150
  3  ω    -44.00  31.00   0.50    0.75    --  -38.50  19.00 -60.00  150
  4  ω    -44.00  31.00   0.50    0.75    --  -38.50  19.00   0.00  150
  5  ω     23.00 100.00   0.50    0.75    --   48.81-125.00 150.00  154
  6  ω     93.00 169.00   0.50    2.99    --  106.38  61.00-180.00  152
  7  ω     41.00 122.00   0.50    2.99    --  106.38-125.00 120.00  162
  8  ω     38.00 115.00   0.50    2.99    --  106.38 -15.00-120.00  154
  9  ω     42.00 111.00   0.50    2.99    --  106.38 -45.00  60.00  138
 10  ω     42.00 130.00   0.50    2.99    --  106.38 -77.00 -60.00  176
 11  ω     38.00 110.00   0.50    2.99    --  106.38 -30.00-180.00  144
 12  ω     38.00 110.00   0.50    2.99    --  106.38 -30.00   0.00  144
 13  ω     38.00 110.00   0.50    2.99    --  106.38 -30.00 -60.00  144
 14  ω     38.00 109.00   0.50    2.99    --  106.38 -94.00-150.00  142
 15  ω     38.00 109.00   0.50    2.99    --  106.38 -94.00 -60.00  142
 16  ω     38.00 109.00   0.50    2.99    --  106.38 -94.00-180.00  142
 17  ω     38.00 115.00   0.50    2.99    --  106.38 -15.00  90.00  154
 18  ω    102.00 171.00   0.50    2.99    --  106.38  45.00 120.00  138
 19  ω     38.00 115.00   0.50    2.99    --  106.38 -15.00 150.00  154
 20  ω     25.00 113.00   0.50    0.75    --   48.81  77.00 -60.00  176
 21  ω     25.00 113.00   0.50    0.75    --   48.81  77.00  30.00  176
 22  ω     25.00 113.00   0.50    0.75    --   48.81  77.00 120.00  176
 23  ω     25.00 113.00   0.50    0.75    --   48.81  77.00-120.00  176
 24  ω     83.00 171.00   0.50    2.99    --  106.38  77.00 -90.00  176
 25  ω    103.00 175.00   0.50    2.99    --  106.38  30.00-120.00  144
 26  ω     98.00 175.00   0.50    2.99    --  106.38  15.00   0.00  154
 27  ω     83.00 171.00   0.50    2.99    --  106.38  77.00   0.00  176
 28  ω     98.00 175.00   0.50    2.99    --  106.38  15.00 -60.00  154
 29  ω     93.00 169.00   0.50    2.99    --  106.38  61.00  90.00  152
 30  ω     93.00 169.00   0.50    2.99    --  106.38  61.00 150.00  152
 31  ω     83.00 171.00   0.50    2.99    --  106.38  77.00  30.00  176
 32  ω     83.00 171.00   0.50    2.99    --  106.38  77.00 -60.00  176
 33  ω     83.00 171.00   0.50    2.99    --  106.38  77.00-120.00  176
 34  ω     83.00 171.00   0.50    2.99    --  106.38  77.00 120.00  176
 35  ω     83.00 171.00   0.50    2.99    --  106.38  77.00  60.00  176
 36  ω     37.00 112.00   0.50    0.75    --   48.81  57.00   0.00  150
 37  ω     25.00 113.00   0.50    0.75    --   48.81  77.00  90.00  176
 38  ω     25.00 113.00   0.50    0.75    --   48.81  77.00-180.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Pilatus 200/300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0216779000
_diffrn_orient_matrix_UB_12      -0.0912923000
_diffrn_orient_matrix_UB_13      0.0018015000
_diffrn_orient_matrix_UB_21      0.0049648000
_diffrn_orient_matrix_UB_22      -0.0335195000
_diffrn_orient_matrix_UB_23      -0.0655143000
_diffrn_orient_matrix_UB_31      0.2182790000
_diffrn_orient_matrix_UB_32      0.0081254000
_diffrn_orient_matrix_UB_33      0.0070935000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9705
_reflns_number_total             11371
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.927
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     811
_refine_ls_number_reflns         11371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0650
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0605P)²+13.7823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1609
_refine_ls_wR_factor_ref         0.1678
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C14(H14), C15(H15), C51(H51), C53(H53), C54(H54),
 C55(H55), C41(H41), C43(H43), C44(H44), C45(H45), C22(H22), C24(H24), C25(H25),
  C26(H26), C61(H61), C63(H63), C64(H64), C65(H65), C31(H31), C33(H33),
 C34(H34), C35(H35)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
S1 S 1.08841(16) 0.25097(7) 1.05961(4) 0.0257(2) Uani 1 1 d . . . . .
S2 S 1.04979(16) 0.12754(7) 1.00191(4) 0.0249(2) Uani 1 1 d . . . . .
F10 F 1.0651(5) 0.52496(18) 0.85605(13) 0.0411(7) Uani 1 1 d . . . . .
F11 F 1.1474(4) 0.53462(17) 0.94236(12) 0.0379(7) Uani 1 1 d . . . . .
F12 F 0.8524(4) 0.51824(17) 0.91469(13) 0.0389(7) Uani 1 1 d . . . . .
N1 N 1.0643(6) 0.2939(2) 1.01026(15) 0.0256(8) Uani 1 1 d . . . . .
N2 N 1.0208(5) 0.1565(2) 0.94482(15) 0.0240(7) Uani 1 1 d . . . . .
C1 C 1.0336(6) 0.2405(3) 0.95735(18) 0.0233(8) Uani 1 1 d . . . . .
C10 C 1.0143(6) 0.2766(3) 0.91019(17) 0.0212(8) Uani 1 1 d . . . . .
C11 C 1.0199(6) 0.3636(3) 0.92406(18) 0.0243(9) Uani 1 1 d . . . . .
H11 H 1.0329 0.3977 0.9622 0.029 Uiso 1 1 calc R . . . .
C12 C 1.0060(6) 0.3994(3) 0.88106(18) 0.0226(8) Uani 1 1 d . . . . .
C13 C 0.9857(6) 0.3497(3) 0.82381(18) 0.0253(9) Uani 1 1 d . . . . .
H13 H 0.9778 0.3742 0.7952 0.030 Uiso 1 1 calc R . . . .
C14 C 0.9774(6) 0.2624(3) 0.80989(18) 0.0243(9) Uani 1 1 d . . . . .
H14 H 0.9619 0.2281 0.7718 0.029 Uiso 1 1 calc R . . . .
C15 C 0.9924(6) 0.2265(3) 0.85296(18) 0.0231(8) Uani 1 1 d . . . . .
H15 H 0.9878 0.1683 0.8434 0.028 Uiso 1 1 calc R . . . .
C16 C 1.0169(7) 0.4939(3) 0.89806(19) 0.0267(9) Uani 1 1 d . . . . .
S9 S -0.16867(16) -0.01648(6) 0.17304(4) 0.0253(2) Uani 1 1 d . . . . .
S10 S -0.19765(17) 0.02778(7) 0.10390(4) 0.0259(2) Uani 1 1 d . . . . .
F50 F -0.0951(10) 0.2728(3) 0.41527(14) 0.105(2) Uani 1 1 d . . . . .
F51 F -0.3044(6) 0.3501(4) 0.41874(15) 0.0799(14) Uani 1 1 d . . . . .
F52 F -0.0183(6) 0.4053(2) 0.43117(13) 0.0596(10) Uani 1 1 d . . . . .
N9 N -0.1507(6) 0.0770(2) 0.22126(15) 0.0250(8) Uani 1 1 d . . . . .
N10 N -0.1824(6) 0.1274(2) 0.14368(15) 0.0257(8) Uani 1 1 d . . . . .
C5 C -0.1611(6) 0.1397(3) 0.19997(18) 0.0218(8) Uani 1 1 d . . . . .
C50 C -0.1439(6) 0.2267(3) 0.24098(18) 0.0227(8) Uani 1 1 d . . . . .
C51 C -0.1498(6) 0.2394(3) 0.29928(18) 0.0229(8) Uani 1 1 d . . . . .
H51 H -0.1665 0.1933 0.3126 0.027 Uiso 1 1 calc R . . . .
C52 C -0.1307(6) 0.3213(3) 0.33748(19) 0.0254(9) Uani 1 1 d . . . . .
C53 C -0.1064(7) 0.3906(3) 0.31786(19) 0.0262(9) Uani 1 1 d . . . . .
H53 H -0.0953 0.4452 0.3436 0.031 Uiso 1 1 calc R . . . .
C54 C -0.0990(7) 0.3781(3) 0.2599(2) 0.0286(9) Uani 1 1 d . . . . .
H54 H -0.0819 0.4244 0.2468 0.034 Uiso 1 1 calc R . . . .
C55 C -0.1169(6) 0.2966(3) 0.22145(18) 0.0253(9) Uani 1 1 d . . . . .
H55 H -0.1110 0.2884 0.1826 0.030 Uiso 1 1 calc R . . . .
C56 C -0.1341(8) 0.3361(3) 0.4003(2) 0.0331(10) Uani 1 1 d . . . . .
S7 S 0.50195(16) 0.05639(7) 0.32198(4) 0.0255(2) Uani 1 1 d . . . . .
S8 S 0.52518(16) -0.03196(7) 0.36434(4) 0.0255(2) Uani 1 1 d . . . . .
F00S F 0.2015(6) 0.4242(2) 0.5595(2) 0.0724(13) Uani 1 1 d . . . . .
F40 F 0.3567(6) 0.41132(19) 0.48646(13) 0.0483(8) Uani 1 1 d . . . . .
F41 F 0.5040(6) 0.4556(2) 0.56868(17) 0.0619(11) Uani 1 1 d . . . . .
N7 N 0.4616(6) 0.1303(2) 0.37903(15) 0.0261(8) Uani 1 1 d . . . . .
N8 N 0.4882(5) 0.0317(2) 0.42663(15) 0.0252(8) Uani 1 1 d . . . . .
C4 C 0.4598(6) 0.1076(3) 0.42700(18) 0.0240(8) Uani 1 1 d . . . . .
C40 C 0.4206(6) 0.1702(3) 0.48094(18) 0.0248(9) Uani 1 1 d . . . . .
C41 C 0.4013(7) 0.2513(3) 0.48267(18) 0.0260(9) Uani 1 1 d . . . . .
H41 H 0.4061 0.2659 0.4494 0.031 Uiso 1 1 calc R . . . .
C42 C 0.3747(6) 0.3108(3) 0.53416(19) 0.0257(9) Uani 1 1 d . . . . .
C43 C 0.3637(7) 0.2891(3) 0.58406(19) 0.0273(9) Uani 1 1 d . . . . .
H43 H 0.3447 0.3290 0.6184 0.033 Uiso 1 1 calc R . . . .
C44 C 0.3814(7) 0.2077(3) 0.58204(18) 0.0290(10) Uani 1 1 d . . . . .
H44 H 0.3756 0.1931 0.6153 0.035 Uiso 1 1 calc R . . . .
C45 C 0.4075(6) 0.1478(3) 0.53097(19) 0.0257(9) Uani 1 1 d . . . . .
H45 H 0.4163 0.0928 0.5297 0.031 Uiso 1 1 calc R . . . .
C46 C 0.3590(7) 0.3996(3) 0.5371(2) 0.0315(10) Uani 1 1 d . . . . .
S3 S 0.65851(16) 0.23511(7) 1.07683(4) 0.0255(2) Uani 1 1 d . . . . .
S4 S 0.60977(16) 0.11327(7) 1.01667(4) 0.0253(2) Uani 1 1 d . . . . .
F20 F 0.5593(5) 0.12848(19) 0.76363(11) 0.0408(7) Uani 1 1 d . . . . .
F21 F 0.5613(5) 0.2383(2) 0.73791(12) 0.0428(7) Uani 1 1 d . . . . .
F22 F 0.2975(4) 0.1671(2) 0.74834(13) 0.0496(9) Uani 1 1 d . . . . .
N3 N 0.6104(6) 0.2813(2) 1.03080(15) 0.0264(8) Uani 1 1 d . . . . .
N4 N 0.5640(6) 0.1455(2) 0.96268(15) 0.0249(8) Uani 1 1 d . . . . .
C20 C 0.5691(6) 0.2293(3) 0.97711(18) 0.0218(8) Uani 1 1 d . . . . .
C21 C 0.5286(6) 0.2662(3) 0.93188(18) 0.0223(8) Uani 1 1 d . . . . .
C22 C 0.5162(6) 0.2162(3) 0.87490(18) 0.0240(8) Uani 1 1 d . . . . .
H22 H 0.5276 0.1593 0.8654 0.029 Uiso 1 1 calc R . . . .
C23 C 0.4872(6) 0.2506(3) 0.83236(18) 0.0247(9) Uani 1 1 d . . . . .
C24 C 0.4691(6) 0.3361(3) 0.84631(19) 0.0271(9) Uani 1 1 d . . . . .
H24 H 0.4500 0.3593 0.8176 0.032 Uiso 1 1 calc R . . . .
C25 C 0.4798(6) 0.3858(3) 0.9034(2) 0.0271(9) Uani 1 1 d . . . . .
H25 H 0.4662 0.4425 0.9130 0.033 Uiso 1 1 calc R . . . .
C26 C 0.5108(6) 0.3513(3) 0.94628(19) 0.0252(9) Uani 1 1 d . . . . .
H26 H 0.5196 0.3849 0.9845 0.030 Uiso 1 1 calc R . . . .
C027 C 0.4771(7) 0.1978(3) 0.77126(19) 0.0274(9) Uani 1 1 d . . . . .
S11 S 0.75834(17) 0.95674(7) 0.90398(4) 0.0262(2) Uani 1 1 d . . . . .
S12 S 0.72848(17) 0.99504(7) 0.83228(5) 0.0267(2) Uani 1 1 d . . . . .
F60 F 0.5041(5) 0.55982(19) 0.84506(13) 0.0469(8) Uani 1 1 d . . . . .
F61 F 0.6955(5) 0.49201(19) 0.79085(13) 0.0421(7) Uani 1 1 d . . . . .
F62 F 0.4003(5) 0.4712(2) 0.76226(16) 0.0567(10) Uani 1 1 d . . . . .
N11 N 0.7273(6) 0.8559(2) 0.86761(15) 0.0243(7) Uani 1 1 d . . . . .
N12 N 0.6913(6) 0.8987(2) 0.78683(15) 0.0263(8) Uani 1 1 d . . . . .
C6 C 0.6942(6) 0.8384(3) 0.81093(18) 0.0235(8) Uani 1 1 d . . . . .
C60 C 0.6552(6) 0.7483(3) 0.77411(18) 0.0240(9) Uani 1 1 d . . . . .
C61 C 0.6202(6) 0.6842(3) 0.79861(17) 0.0225(8) Uani 1 1 d . . . . .
H61 H 0.6212 0.6980 0.8382 0.027 Uiso 1 1 calc R . . . .
C62 C 0.5838(6) 0.5999(3) 0.76419(19) 0.0242(9) Uani 1 1 d . . . . .
C63 C 0.5872(7) 0.5789(3) 0.7051(2) 0.0312(10) Uani 1 1 d . . . . .
H63 H 0.5666 0.5224 0.6821 0.037 Uiso 1 1 calc R . . . .
C64 C 0.6212(7) 0.6421(3) 0.6808(2) 0.0312(10) Uani 1 1 d . . . . .
H64 H 0.6214 0.6280 0.6412 0.037 Uiso 1 1 calc R . . . .
C65 C 0.6548(6) 0.7264(3) 0.71445(19) 0.0264(9) Uani 1 1 d . . . . .
H65 H 0.6772 0.7685 0.6975 0.032 Uiso 1 1 calc R . . . .
C66 C 0.5467(7) 0.5316(3) 0.7907(2) 0.0323(10) Uani 1 1 d . . . . .
S5 S 0.91571(16) 0.01363(7) 0.70720(4) 0.0253(2) Uani 1 1 d . . . . .
S6 S 0.97025(16) -0.07264(7) 0.62931(4) 0.0254(2) Uani 1 1 d . . . . .
F30 F 0.8307(5) 0.41899(17) 0.61939(12) 0.0370(7) Uani 1 1 d . . . . .
F31 F 0.7313(5) 0.36541(18) 0.68336(13) 0.0441(8) Uani 1 1 d . . . . .
F32 F 1.0308(5) 0.40228(18) 0.68007(13) 0.0440(8) Uani 1 1 d . . . . .
N5 N 0.8991(5) 0.0895(2) 0.68110(15) 0.0239(7) Uani 1 1 d . . . . .
N6 N 0.9585(5) -0.0066(2) 0.59339(15) 0.0241(7) Uani 1 1 d . . . . .
C3 C 0.9239(6) 0.0688(3) 0.62478(17) 0.0222(8) Uani 1 1 d . . . . .
C30 C 0.9069(6) 0.1348(3) 0.59755(17) 0.0211(8) Uani 1 1 d . . . . .
C31 C 0.8931(6) 0.2165(3) 0.63231(18) 0.0237(8) Uani 1 1 d . . . . .
H31 H 0.8947 0.2291 0.6718 0.028 Uiso 1 1 calc R . . . .
C32 C 0.8770(6) 0.2788(3) 0.60780(18) 0.0236(8) Uani 1 1 d . . . . .
C33 C 0.8762(6) 0.2614(3) 0.54901(18) 0.0251(9) Uani 1 1 d . . . . .
H33 H 0.8677 0.3038 0.5329 0.030 Uiso 1 1 calc R . . . .
C34 C 0.8884(7) 0.1798(3) 0.51466(18) 0.0258(9) Uani 1 1 d . . . . .
H34 H 0.8862 0.1673 0.4752 0.031 Uiso 1 1 calc R . . . .
C35 C 0.9039(6) 0.1167(3) 0.53828(17) 0.0225(8) Uani 1 1 d . . . . .
H35 H 0.9122 0.0623 0.5148 0.027 Uiso 1 1 calc R . . . .
C36 C 0.8670(7) 0.3656(3) 0.64654(19) 0.0282(9) Uani 1 1 d . . . . .


_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
S1 S2 2.0918(15) . ?
S1 N1 1.621(4) . ?
S2 N2 1.650(4) . ?
F10 C16 1.336(5) . ?
F11 C16 1.345(5) . ?
F12 C16 1.334(5) . ?
N1 C1 1.322(5) . ?
N2 C1 1.341(5) . ?
C1 C10 1.488(6) . ?
C10 C11 1.392(6) . ?
C10 C15 1.390(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(6) . ?
C12 C13 1.388(6) . ?
C12 C16 1.504(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.395(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.390(6) . ?
C15 H15 0.9300 . ?
S9 S10 2.0870(14) . ?
S9 N9 1.633(4) . ?
S10 N10 1.642(4) . ?
F50 C56 1.301(6) . ?
F51 C56 1.337(7) . ?
F52 C56 1.318(6) . ?
N9 C5 1.332(5) . ?
N10 C5 1.341(5) . ?
C5 C50 1.482(6) . ?
C50 C51 1.391(6) . ?
C50 C55 1.401(6) . ?
C51 H51 0.9300 . ?
C51 C52 1.389(6) . ?
C52 C53 1.393(6) . ?
C52 C56 1.493(6) . ?
C53 H53 0.9300 . ?
C53 C54 1.384(6) . ?
C54 H54 0.9300 . ?
C54 C55 1.388(6) . ?
C55 H55 0.9300 . ?
S7 S8 2.0977(14) . ?
S7 N7 1.626(4) . ?
S8 N8 1.629(4) . ?
F00S C46 1.330(6) . ?
F40 C46 1.327(6) . ?
F41 C46 1.328(6) . ?
N7 C4 1.356(5) . ?
N8 C4 1.324(6) . ?
C4 C40 1.480(6) . ?
C40 C41 1.383(6) . ?
C40 C45 1.405(6) . ?
C41 H41 0.9300 . ?
C41 C42 1.388(6) . ?
C42 C43 1.395(6) . ?
C42 C46 1.499(6) . ?
C43 H43 0.9300 . ?
C43 C44 1.384(7) . ?
C44 H44 0.9300 . ?
C44 C45 1.383(6) . ?
C45 H45 0.9300 . ?
S3 S4 2.0933(15) . ?
S3 N3 1.625(4) . ?
S4 N4 1.634(4) . ?
F20 C027 1.348(5) . ?
F21 C027 1.332(5) . ?
F22 C027 1.341(6) . ?
N3 C20 1.335(6) . ?
N4 C20 1.340(5) . ?
C20 C21 1.482(6) . ?
C21 C22 1.386(6) . ?
C21 C26 1.394(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.377(6) . ?
C23 C24 1.399(6) . ?
C23 C027 1.485(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.389(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.387(6) . ?
C26 H26 0.9300 . ?
S11 S12 2.0855(15) . ?
S11 N11 1.631(4) . ?
S12 N12 1.635(4) . ?
F60 C66 1.337(6) . ?
F61 C66 1.336(6) . ?
F62 C66 1.345(6) . ?
N11 C6 1.343(5) . ?
N12 C6 1.335(5) . ?
C6 C60 1.483(6) . ?
C60 C61 1.394(6) . ?
C60 C65 1.402(6) . ?
C61 H61 0.9300 . ?
C61 C62 1.388(6) . ?
C62 C63 1.392(6) . ?
C62 C66 1.491(6) . ?
C63 H63 0.9300 . ?
C63 C64 1.377(7) . ?
C64 H64 0.9300 . ?
C64 C65 1.382(7) . ?
C65 H65 0.9300 . ?
S5 S6 2.1017(15) . ?
S5 N5 1.623(4) . ?
S6 N6 1.640(4) . ?
F30 C36 1.332(5) . ?
F31 C36 1.348(6) . ?
F32 C36 1.354(6) . ?
N5 C3 1.348(5) . ?
N6 C3 1.328(5) . ?
C3 C30 1.489(6) . ?
C30 C31 1.395(6) . ?
C30 C35 1.398(6) . ?
C31 H31 0.9300 . ?
C31 C32 1.387(6) . ?
C32 C33 1.388(6) . ?
C32 C36 1.487(6) . ?
C33 H33 0.9300 . ?
C33 C34 1.389(6) . ?
C34 H34 0.9300 . ?
C34 C35 1.382(6) . ?
C35 H35 0.9300 . ?

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
N1 S1 S2 94.05(14) . . ?
N2 S2 S1 94.62(14) . . ?
C1 N1 S1 115.4(3) . . ?
C1 N2 S2 113.0(3) . . ?
N1 C1 N2 122.9(4) . . ?
N1 C1 C10 117.7(4) . . ?
N2 C1 C10 119.4(4) . . ?
C11 C10 C1 118.7(4) . . ?
C15 C10 C1 122.2(4) . . ?
C15 C10 C11 119.1(4) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.1(4) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 121.0(4) . . ?
C11 C12 C16 118.2(4) . . ?
C13 C12 C16 120.8(4) . . ?
C12 C13 H13 120.5 . . ?
C12 C13 C14 119.0(4) . . ?
C14 C13 H13 120.5 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.1(4) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 C14 120.8(4) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
F10 C16 F11 106.3(4) . . ?
F10 C16 C12 113.2(4) . . ?
F11 C16 C12 111.5(4) . . ?
F12 C16 F10 106.8(4) . . ?
F12 C16 F11 106.1(4) . . ?
F12 C16 C12 112.4(4) . . ?
N9 S9 S10 94.45(14) . . ?
N10 S10 S9 94.70(14) . . ?
C5 N9 S9 114.4(3) . . ?
C5 N10 S10 113.5(3) . . ?
N9 C5 N10 122.9(4) . . ?
N9 C5 C50 117.7(4) . . ?
N10 C5 C50 119.4(4) . . ?
C51 C50 C5 120.1(4) . . ?
C51 C50 C55 119.6(4) . . ?
C55 C50 C5 120.2(4) . . ?
C50 C51 H51 120.2 . . ?
C52 C51 C50 119.7(4) . . ?
C52 C51 H51 120.2 . . ?
C51 C52 C53 120.6(4) . . ?
C51 C52 C56 120.4(4) . . ?
C53 C52 C56 119.1(4) . . ?
C52 C53 H53 120.1 . . ?
C54 C53 C52 119.9(4) . . ?
C54 C53 H53 120.1 . . ?
C53 C54 H54 120.0 . . ?
C53 C54 C55 120.0(4) . . ?
C55 C54 H54 120.0 . . ?
C50 C55 H55 119.9 . . ?
C54 C55 C50 120.2(4) . . ?
C54 C55 H55 119.9 . . ?
F50 C56 F51 106.3(5) . . ?
F50 C56 F52 108.5(5) . . ?
F50 C56 C52 113.4(4) . . ?
F51 C56 C52 112.0(4) . . ?
F52 C56 F51 103.2(4) . . ?
F52 C56 C52 112.7(4) . . ?
N7 S7 S8 94.55(14) . . ?
N8 S8 S7 94.25(14) . . ?
C4 N7 S7 114.0(3) . . ?
C4 N8 S8 114.9(3) . . ?
N7 C4 C40 118.0(4) . . ?
N8 C4 N7 122.3(4) . . ?
N8 C4 C40 119.8(4) . . ?
C41 C40 C4 120.4(4) . . ?
C41 C40 C45 119.8(4) . . ?
C45 C40 C4 119.8(4) . . ?
C40 C41 H41 120.1 . . ?
C40 C41 C42 119.8(4) . . ?
C42 C41 H41 120.1 . . ?
C41 C42 C43 120.5(4) . . ?
C41 C42 C46 120.5(4) . . ?
C43 C42 C46 119.0(4) . . ?
C42 C43 H43 120.3 . . ?
C44 C43 C42 119.4(4) . . ?
C44 C43 H43 120.3 . . ?
C43 C44 H44 119.7 . . ?
C45 C44 C43 120.5(4) . . ?
C45 C44 H44 119.7 . . ?
C40 C45 H45 120.1 . . ?
C44 C45 C40 119.8(4) . . ?
C44 C45 H45 120.1 . . ?
F00S C46 C42 112.9(4) . . ?
F40 C46 F00S 105.5(4) . . ?
F40 C46 F41 105.5(4) . . ?
F40 C46 C42 113.7(4) . . ?
F41 C46 F00S 106.5(4) . . ?
F41 C46 C42 112.1(4) . . ?
N3 S3 S4 94.36(14) . . ?
N4 S4 S3 94.47(14) . . ?
C20 N3 S3 114.6(3) . . ?
C20 N4 S4 114.0(3) . . ?
N3 C20 N4 122.5(4) . . ?
N3 C20 C21 118.4(4) . . ?
N4 C20 C21 119.0(4) . . ?
C22 C21 C20 119.5(4) . . ?
C22 C21 C26 120.1(4) . . ?
C26 C21 C20 120.4(4) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.1(4) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C24 120.3(4) . . ?
C22 C23 C027 120.3(4) . . ?
C24 C23 C027 119.4(4) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 C23 119.5(4) . . ?
C25 C24 H24 120.3 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.2(4) . . ?
C26 C25 H25 119.9 . . ?
C21 C26 H26 120.1 . . ?
C25 C26 C21 119.8(4) . . ?
C25 C26 H26 120.1 . . ?
F20 C027 C23 112.5(4) . . ?
F21 C027 F20 106.0(4) . . ?
F21 C027 F22 106.6(4) . . ?
F21 C027 C23 113.8(4) . . ?
F22 C027 F20 104.5(4) . . ?
F22 C027 C23 112.7(4) . . ?
N11 S11 S12 94.72(13) . . ?
N12 S12 S11 94.48(14) . . ?
C6 N11 S11 114.1(3) . . ?
C6 N12 S12 114.2(3) . . ?
N11 C6 C60 118.5(4) . . ?
N12 C6 N11 122.5(4) . . ?
N12 C6 C60 119.0(4) . . ?
C61 C60 C6 120.2(4) . . ?
C61 C60 C65 119.1(4) . . ?
C65 C60 C6 120.7(4) . . ?
C60 C61 H61 119.9 . . ?
C62 C61 C60 120.2(4) . . ?
C62 C61 H61 119.9 . . ?
C61 C62 C63 120.1(4) . . ?
C61 C62 C66 119.9(4) . . ?
C63 C62 C66 119.9(4) . . ?
C62 C63 H63 120.1 . . ?
C64 C63 C62 119.8(4) . . ?
C64 C63 H63 120.1 . . ?
C63 C64 H64 119.6 . . ?
C63 C64 C65 120.8(4) . . ?
C65 C64 H64 119.6 . . ?
C60 C65 H65 120.0 . . ?
C64 C65 C60 120.0(4) . . ?
C64 C65 H65 120.0 . . ?
F60 C66 F62 106.5(4) . . ?
F60 C66 C62 113.3(4) . . ?
F61 C66 F60 106.2(4) . . ?
F61 C66 F62 106.0(4) . . ?
F61 C66 C62 112.7(4) . . ?
F62 C66 C62 111.7(4) . . ?
N5 S5 S6 94.79(13) . . ?
N6 S6 S5 94.09(14) . . ?
C3 N5 S5 113.8(3) . . ?
C3 N6 S6 114.0(3) . . ?
N5 C3 C30 116.9(4) . . ?
N6 C3 N5 123.3(4) . . ?
N6 C3 C30 119.8(4) . . ?
C31 C30 C3 118.8(4) . . ?
C31 C30 C35 119.5(4) . . ?
C35 C30 C3 121.7(4) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 C30 119.8(4) . . ?
C32 C31 H31 120.1 . . ?
C31 C32 C33 121.0(4) . . ?
C31 C32 C36 118.0(4) . . ?
C33 C32 C36 121.0(4) . . ?
C32 C33 H33 120.6 . . ?
C32 C33 C34 118.9(4) . . ?
C34 C33 H33 120.6 . . ?
C33 C34 H34 119.5 . . ?
C35 C34 C33 121.0(4) . . ?
C35 C34 H34 119.5 . . ?
C30 C35 H35 120.0 . . ?
C34 C35 C30 119.9(4) . . ?
C34 C35 H35 120.0 . . ?
F30 C36 F31 106.4(4) . . ?
F30 C36 F32 106.3(4) . . ?
F30 C36 C32 114.0(4) . . ?
F31 C36 F32 105.0(4) . . ?
F31 C36 C32 112.2(4) . . ?
F32 C36 C32 112.4(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 S2 N2 C1 0.3(3) . . . . ?
S1 N1 C1 N2 0.8(6) . . . . ?
S1 N1 C1 C10 -178.8(3) . . . . ?
S2 S1 N1 C1 -0.4(3) . . . . ?
S2 N2 C1 N1 -0.7(6) . . . . ?
S2 N2 C1 C10 178.8(3) . . . . ?
N1 C1 C10 C11 -3.1(6) . . . . ?
N1 C1 C10 C15 176.4(4) . . . . ?
N2 C1 C10 C11 177.3(4) . . . . ?
N2 C1 C10 C15 -3.2(6) . . . . ?
C1 C10 C11 C12 178.7(4) . . . . ?
C1 C10 C15 C14 -179.1(4) . . . . ?
C10 C11 C12 C13 0.2(7) . . . . ?
C10 C11 C12 C16 -178.7(4) . . . . ?
C11 C10 C15 C14 0.4(6) . . . . ?
C11 C12 C13 C14 0.7(7) . . . . ?
C11 C12 C16 F10 159.1(4) . . . . ?
C11 C12 C16 F11 39.3(6) . . . . ?
C11 C12 C16 F12 -79.7(5) . . . . ?
C12 C13 C14 C15 -1.0(7) . . . . ?
C13 C12 C16 F10 -19.8(6) . . . . ?
C13 C12 C16 F11 -139.6(4) . . . . ?
C13 C12 C16 F12 101.3(5) . . . . ?
C13 C14 C15 C10 0.5(7) . . . . ?
C15 C10 C11 C12 -0.7(6) . . . . ?
C16 C12 C13 C14 179.6(4) . . . . ?
S9 S10 N10 C5 -0.6(3) . . . . ?
S9 N9 C5 N10 -0.7(6) . . . . ?
S9 N9 C5 C50 -179.3(3) . . . . ?
S10 S9 N9 C5 0.2(3) . . . . ?
S10 N10 C5 N9 0.9(6) . . . . ?
S10 N10 C5 C50 179.5(3) . . . . ?
N9 C5 C50 C51 -10.7(6) . . . . ?
N9 C5 C50 C55 167.7(4) . . . . ?
N10 C5 C50 C51 170.6(4) . . . . ?
N10 C5 C50 C55 -11.0(6) . . . . ?
C5 C50 C51 C52 179.0(4) . . . . ?
C5 C50 C55 C54 -179.4(4) . . . . ?
C50 C51 C52 C53 0.3(7) . . . . ?
C50 C51 C52 C56 -179.2(4) . . . . ?
C51 C50 C55 C54 -0.9(7) . . . . ?
C51 C52 C53 C54 -0.8(7) . . . . ?
C51 C52 C56 F50 20.7(7) . . . . ?
C51 C52 C56 F51 -99.6(5) . . . . ?
C51 C52 C56 F52 144.5(5) . . . . ?
C52 C53 C54 C55 0.4(7) . . . . ?
C53 C52 C56 F50 -158.8(5) . . . . ?
C53 C52 C56 F51 81.0(6) . . . . ?
C53 C52 C56 F52 -35.0(7) . . . . ?
C53 C54 C55 C50 0.4(7) . . . . ?
C55 C50 C51 C52 0.6(7) . . . . ?
C56 C52 C53 C54 178.7(4) . . . . ?
S7 S8 N8 C4 0.1(3) . . . . ?
S7 N7 C4 N8 -0.1(6) . . . . ?
S7 N7 C4 C40 -178.9(3) . . . . ?
S8 S7 N7 C4 0.2(3) . . . . ?
S8 N8 C4 N7 -0.1(6) . . . . ?
S8 N8 C4 C40 178.7(3) . . . . ?
N7 C4 C40 C41 -4.8(6) . . . . ?
N7 C4 C40 C45 176.7(4) . . . . ?
N8 C4 C40 C41 176.4(4) . . . . ?
N8 C4 C40 C45 -2.2(6) . . . . ?
C4 C40 C41 C42 -176.6(4) . . . . ?
C4 C40 C45 C44 176.4(4) . . . . ?
C40 C41 C42 C43 -1.2(7) . . . . ?
C40 C41 C42 C46 178.3(4) . . . . ?
C41 C40 C45 C44 -2.1(7) . . . . ?
C41 C42 C43 C44 0.6(7) . . . . ?
C41 C42 C46 F00S 125.5(5) . . . . ?
C41 C42 C46 F40 5.4(7) . . . . ?
C41 C42 C46 F41 -114.2(5) . . . . ?
C42 C43 C44 C45 -0.7(7) . . . . ?
C43 C42 C46 F00S -55.0(6) . . . . ?
C43 C42 C46 F40 -175.1(4) . . . . ?
C43 C42 C46 F41 65.3(6) . . . . ?
C43 C44 C45 C40 1.5(7) . . . . ?
C45 C40 C41 C42 1.9(7) . . . . ?
C46 C42 C43 C44 -178.9(4) . . . . ?
S3 S4 N4 C20 -1.9(3) . . . . ?
S3 N3 C20 N4 1.3(6) . . . . ?
S3 N3 C20 C21 -178.3(3) . . . . ?
S4 S3 N3 C20 -2.1(3) . . . . ?
S4 N4 C20 N3 0.8(6) . . . . ?
S4 N4 C20 C21 -179.6(3) . . . . ?
N3 C20 C21 C22 169.5(4) . . . . ?
N3 C20 C21 C26 -7.9(6) . . . . ?
N4 C20 C21 C22 -10.1(6) . . . . ?
N4 C20 C21 C26 172.5(4) . . . . ?
C20 C21 C22 C23 -177.1(4) . . . . ?
C20 C21 C26 C25 177.6(4) . . . . ?
C21 C22 C23 C24 -0.3(7) . . . . ?
C21 C22 C23 C027 179.0(4) . . . . ?
C22 C21 C26 C25 0.3(7) . . . . ?
C22 C23 C24 C25 -0.3(7) . . . . ?
C22 C23 C027 F20 -20.7(6) . . . . ?
C22 C23 C027 F21 -141.3(4) . . . . ?
C22 C23 C027 F22 97.2(5) . . . . ?
C23 C24 C25 C26 0.9(7) . . . . ?
C24 C23 C027 F20 158.6(4) . . . . ?
C24 C23 C027 F21 38.0(6) . . . . ?
C24 C23 C027 F22 -83.6(5) . . . . ?
C24 C25 C26 C21 -0.9(7) . . . . ?
C26 C21 C22 C23 0.3(7) . . . . ?
C027 C23 C24 C25 -179.6(4) . . . . ?
S11 S12 N12 C6 0.0(3) . . . . ?
S11 N11 C6 N12 1.3(6) . . . . ?
S11 N11 C6 C60 -177.2(3) . . . . ?
S12 S11 N11 C6 -1.0(3) . . . . ?
S12 N12 C6 N11 -0.8(6) . . . . ?
S12 N12 C6 C60 177.8(3) . . . . ?
N11 C6 C60 C61 11.3(6) . . . . ?
N11 C6 C60 C65 -168.1(4) . . . . ?
N12 C6 C60 C61 -167.3(4) . . . . ?
N12 C6 C60 C65 13.3(6) . . . . ?
C6 C60 C61 C62 -179.9(4) . . . . ?
C6 C60 C65 C64 179.0(4) . . . . ?
C60 C61 C62 C63 1.7(7) . . . . ?
C60 C61 C62 C66 179.9(4) . . . . ?
C61 C60 C65 C64 -0.4(7) . . . . ?
C61 C62 C63 C64 -1.9(7) . . . . ?
C61 C62 C66 F60 16.4(6) . . . . ?
C61 C62 C66 F61 -104.2(5) . . . . ?
C61 C62 C66 F62 136.6(5) . . . . ?
C62 C63 C64 C65 1.0(7) . . . . ?
C63 C62 C66 F60 -165.5(4) . . . . ?
C63 C62 C66 F61 74.0(5) . . . . ?
C63 C62 C66 F62 -45.2(6) . . . . ?
C63 C64 C65 C60 0.2(7) . . . . ?
C65 C60 C61 C62 -0.6(6) . . . . ?
C66 C62 C63 C64 179.9(4) . . . . ?
S5 S6 N6 C3 0.5(3) . . . . ?
S5 N5 C3 N6 0.1(6) . . . . ?
S5 N5 C3 C30 178.8(3) . . . . ?
S6 S5 N5 C3 0.2(3) . . . . ?
S6 N6 C3 N5 -0.5(6) . . . . ?
S6 N6 C3 C30 -179.2(3) . . . . ?
N5 C3 C30 C31 8.7(6) . . . . ?
N5 C3 C30 C35 -171.1(4) . . . . ?
N6 C3 C30 C31 -172.5(4) . . . . ?
N6 C3 C30 C35 7.7(6) . . . . ?
C3 C30 C31 C32 -180.0(4) . . . . ?
C3 C30 C35 C34 -179.8(4) . . . . ?
C30 C31 C32 C33 -0.6(7) . . . . ?
C30 C31 C32 C36 -178.7(4) . . . . ?
C31 C30 C35 C34 0.4(7) . . . . ?
C31 C32 C33 C34 1.2(7) . . . . ?
C31 C32 C36 F30 -173.0(4) . . . . ?
C31 C32 C36 F31 -52.0(6) . . . . ?
C31 C32 C36 F32 65.9(5) . . . . ?
C32 C33 C34 C35 -0.9(7) . . . . ?
C33 C32 C36 F30 9.0(6) . . . . ?
C33 C32 C36 F31 129.9(4) . . . . ?
C33 C32 C36 F32 -112.1(5) . . . . ?
C33 C34 C35 C30 0.2(7) . . . . ?
C35 C30 C31 C32 -0.2(7) . . . . ?
C36 C32 C33 C34 179.1(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method 
'MiTeGen 100um polymer mount, with ParatoneTM oil.'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.102
_oxdiff_exptl_absorpt_empirical_full_min 0.503
_chemical_compound_source        No.
_chemical_properties_physical    
', Air-sensitive,Oxygen-sensitive, Oxygen-sensitive'
####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 1512476'
_audit_update_record             
;
2017-06-19 deposited with the CCDC.
2017-06-20 downloaded from the CCDC.
;
# Shelx code: rb06040
_audit_creation_date             2016-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 4-(3-cyano-5-tertbutyl-phenyl)-3H-1,2,3,5-diselenadiazol-3-yl
;
_chemical_formula_moiety         'C12 H12 N3 Se2'
_chemical_formula_sum            'C12 H12 N3 Se2'
_chemical_formula_weight         356.17
_chemical_melting_point          473
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.379(3)
_cell_length_b                   10.667(4)
_cell_length_c                   20.458(7)
_cell_angle_alpha                80.562(4)
_cell_angle_beta                 84.783(4)
_cell_angle_gamma                81.218(4)
_cell_volume                     1990.9(12)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    7983
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.25
_cell_measurement_theta_min      2.33
_exptl_absorpt_coefficient_mu    5.553
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1437 before and 0.0794 after correction.
The Ratio of minimum to maximum transmission is 0.4810.
The λ/2 correction factor is 0.0015.
;
_exptl_special_details           
; 
 A crystal coated in Paratone (TM) oil was mounted on the end of a thin glass
 capillary and cooled in the gas stream of the diffractometer Kryoflex device.
;
_exptl_crystal_recrystallization_method Sublimation
_diffrn_ambient_pressure         101
_exptl_crystal_description       Plate
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_density_meas      .
_exptl_crystal_F_000             1038
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.041
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_unetI/netI     0.1216
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21974
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         27.430
_diffrn_reflns_theta_min         1.955
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.978
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker D8'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
 Bruker ApexII CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 66.06
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5194
_reflns_number_total             8884
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2008)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.185
_refine_diff_density_min         -0.904
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         8884
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      0.918
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1170
_refine_special_details          
;
 A two-part disorder model was developed for the tBu groups attached to C9 and
 C21. Isotropic refinement converged to occupancies of 0.71:0.29 for the major
 and minor components of C9, and to 0.60:0.40 for C21. These occupancies where
 then frozen and anistropic refinement was carried out. EADP restraints were
 used within each of the two sets of tBu groups in order to have a stable
 anisotropic refinement.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C10) = Uanis(C11) = Uanis(C12) = Uanis(C10A) = Uanis(C12A) = Uanis(C11A)
Uanis(C22) = Uanis(C24) = Uanis(C23) = Uanis(C22A) = Uanis(C24A) = Uanis(C23A)
3. Others
 Fixed Sof: C10(0.71) H10A(0.71) H10B(0.71) H10C(0.71) C11(0.71) H11A(0.71)
 H11B(0.71) H11C(0.71) C12(0.71) H12A(0.71) H12B(0.71) H12C(0.71) C10A(0.29)
 H10D(0.29) H10E(0.29) H10F(0.29) C11A(0.29) H11D(0.29) H11E(0.29) H11F(0.29)
 C12A(0.29) H12D(0.29) H12E(0.29) H12F(0.29) C22(0.6) H22A(0.6) H22B(0.6)
 H22C(0.6) C23(0.6) H23A(0.6) H23B(0.6) H23C(0.6) C24(0.6) H24A(0.6) H24B(0.6)
 H24C(0.6) C22A(0.4) H22D(0.4) H22E(0.4) H22F(0.4) C23A(0.4) H23D(0.4)
 H23E(0.4) H23F(0.4) C24A(0.4) H24D(0.4) H24E(0.4) H24F(0.4)
4.a Me refined with riding coordinates:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C10A(H10D,H10E,
 H10F), C11A(H11D,H11E,H11F), C12A(H12D,H12E,H12F), C22(H22A,H22B,H22C),
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C22A(H22D,H22E,H22F), C23A(H23D,H23E,
 H23F), C24A(H24D,H24E,H24F), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C),
 C36(H36A,H36B,H36C)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C15(H15), C17(H17), C19(H19), C27(H27), C29(H29),
 C31(H31)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se -0.04483(6) 0.64166(5) 0.58173(3) 0.03091(15) Uani 1 1 d . . . . .
Se2 Se 0.09135(6) 0.64902(5) 0.66923(3) 0.03391(16) Uani 1 1 d . . . . .
N1 N -0.0438(5) 0.4734(4) 0.6063(2) 0.0288(10) Uani 1 1 d . . . . .
N2 N 0.0949(5) 0.4808(4) 0.6972(2) 0.0348(11) Uani 1 1 d . . . . .
N11 N -0.0068(7) -0.0909(5) 0.5901(3) 0.0658(18) Uani 1 1 d . . . . .
C1 C 0.0239(5) 0.4223(5) 0.6607(3) 0.0271(12) Uani 1 1 d . . . . .
C2 C 0.0121(5) 0.2863(5) 0.6857(3) 0.0284(12) Uani 1 1 d . . . . .
C3 C 0.0020(6) 0.2450(5) 0.7530(3) 0.0387(14) Uani 1 1 d . . . . .
H3 H 0.0081 0.3047 0.7821 0.046 Uiso 1 1 calc R . . . .
C4 C -0.0168(6) 0.1192(6) 0.7808(3) 0.0427(15) Uani 1 1 d . . . . .
C5 C -0.0190(6) 0.0353(6) 0.7367(3) 0.0451(16) Uani 1 1 d . . . . .
H5 H -0.0284 -0.0518 0.7533 0.054 Uiso 1 1 calc R . . . .
C6 C -0.0078(6) 0.0744(5) 0.6689(3) 0.0365(14) Uani 1 1 d . . . . .
C7 C 0.0070(5) 0.2002(5) 0.6425(3) 0.0346(14) Uani 1 1 d . . . . .
H7 H 0.0136 0.2268 0.5958 0.042 Uiso 1 1 calc R . . . .
C8 C -0.0073(7) -0.0189(6) 0.6246(3) 0.0437(16) Uani 1 1 d . . . . .
C9 C -0.0394(8) 0.0809(7) 0.8552(4) 0.0587(19) Uani 1 1 d . . . . .
C10 C -0.1831(13) 0.0303(12) 0.8736(5) 0.086(2) Uani 0.71 1 d . . P A 1
H10A H -0.1952 0.0062 0.9219 0.130 Uiso 0.71 1 calc R . P A 1
H10B H -0.2622 0.0972 0.8586 0.130 Uiso 0.71 1 calc R . P A 1
H10C H -0.1846 -0.0451 0.8521 0.130 Uiso 0.71 1 calc R . P A 1
C11 C 0.0833(13) -0.0180(12) 0.8827(5) 0.086(2) Uani 0.71 1 d . . P A 1
H11A H 0.0650 -0.0404 0.9308 0.130 Uiso 0.71 1 calc R . P A 1
H11B H 0.0895 -0.0951 0.8618 0.130 Uiso 0.71 1 calc R . P A 1
H11C H 0.1745 0.0177 0.8733 0.130 Uiso 0.71 1 calc R . P A 1
C12 C -0.0471(14) 0.1968(11) 0.8961(5) 0.086(2) Uani 0.71 1 d . . P A 1
H12A H -0.0618 0.1653 0.9436 0.130 Uiso 0.71 1 calc R . P A 1
H12B H 0.0436 0.2336 0.8876 0.130 Uiso 0.71 1 calc R . P A 1
H12C H -0.1278 0.2628 0.8822 0.130 Uiso 0.71 1 calc R . P A 1
C10A C -0.181(3) 0.146(3) 0.8728(13) 0.086(2) Uani 0.29 1 d . . P A 2
H10D H -0.2532 0.1203 0.8482 0.130 Uiso 0.29 1 calc R . P A 2
H10E H -0.2039 0.1242 0.9206 0.130 Uiso 0.29 1 calc R . P A 2
H10F H -0.1809 0.2394 0.8616 0.130 Uiso 0.29 1 calc R . P A 2
C11A C 0.086(3) 0.101(3) 0.8837(12) 0.086(2) Uani 0.29 1 d . . P A 2
H11D H 0.1709 0.0485 0.8658 0.130 Uiso 0.29 1 calc R . P A 2
H11E H 0.0985 0.1918 0.8730 0.130 Uiso 0.29 1 calc R . P A 2
H11F H 0.0754 0.0766 0.9320 0.130 Uiso 0.29 1 calc R . P A 2
C12A C -0.048(4) -0.069(3) 0.8692(12) 0.086(2) Uani 0.29 1 d . . P A 2
H12D H -0.1340 -0.0860 0.8500 0.130 Uiso 0.29 1 calc R . P A 2
H12E H 0.0387 -0.1151 0.8489 0.130 Uiso 0.29 1 calc R . P A 2
H12F H -0.0544 -0.0981 0.9172 0.130 Uiso 0.29 1 calc R . P A 2
Se3 Se 0.23200(6) 0.59299(5) 0.48516(3) 0.02985(15) Uani 1 1 d . . . . .
Se4 Se 0.37930(6) 0.60249(5) 0.56824(3) 0.03310(16) Uani 1 1 d . . . . .
N3 N 0.2454(5) 0.4222(4) 0.5081(2) 0.0303(11) Uani 1 1 d . . . . .
N4 N 0.3960(5) 0.4311(4) 0.5941(2) 0.0319(11) Uani 1 1 d . . . . .
N12 N 0.2796(6) -0.1275(5) 0.4672(3) 0.0546(15) Uani 1 1 d . . . . .
C13 C 0.3254(5) 0.3710(5) 0.5577(3) 0.0260(12) Uani 1 1 d . . . . .
C14 C 0.3465(5) 0.2286(5) 0.5732(3) 0.0270(12) Uani 1 1 d . . . . .
C15 C 0.3146(6) 0.1563(5) 0.5285(3) 0.0315(13) Uani 1 1 d . . . . .
H15 H 0.2807 0.1962 0.4867 0.038 Uiso 1 1 calc R . . . .
C16 C 0.3328(6) 0.0227(5) 0.5453(3) 0.0340(14) Uani 1 1 d . . . . .
C17 C 0.3842(6) -0.0352(5) 0.6051(3) 0.0396(15) Uani 1 1 d . . . . .
H17 H 0.3978 -0.1262 0.6151 0.047 Uiso 1 1 calc R . . . .
C18 C 0.4168(6) 0.0355(5) 0.6512(3) 0.0396(15) Uani 1 1 d . . . . .
C19 C 0.3966(6) 0.1679(5) 0.6339(3) 0.0325(13) Uani 1 1 d . . . . .
H19 H 0.4179 0.2190 0.6647 0.039 Uiso 1 1 calc R . . . .
C20 C 0.3036(7) -0.0582(5) 0.4999(3) 0.0406(15) Uani 1 1 d . . . . .
C21 C 0.4773(8) -0.0328(6) 0.7165(3) 0.0562(19) Uani 1 1 d . . . . .
C22 C 0.632(2) -0.0801(15) 0.7070(7) 0.076(2) Uani 0.6 1 d . . P B 1
H22A H 0.6682 -0.1234 0.7495 0.114 Uiso 0.6 1 calc R . P B 1
H22B H 0.6461 -0.1407 0.6750 0.114 Uiso 0.6 1 calc R . P B 1
H22C H 0.6849 -0.0077 0.6900 0.114 Uiso 0.6 1 calc R . P B 1
C23 C 0.3664(17) -0.125(2) 0.7483(9) 0.076(2) Uani 0.6 1 d . . P B 1
H23A H 0.2691 -0.0759 0.7505 0.114 Uiso 0.6 1 calc R . P B 1
H23B H 0.3679 -0.1925 0.7211 0.114 Uiso 0.6 1 calc R . P B 1
H23C H 0.3926 -0.1634 0.7932 0.114 Uiso 0.6 1 calc R . P B 1
C24 C 0.4523(14) 0.0620(16) 0.7679(7) 0.076(2) Uani 0.6 1 d . . P B 1
H24A H 0.3488 0.0929 0.7738 0.114 Uiso 0.6 1 calc R . P B 1
H24B H 0.4876 0.0179 0.8105 0.114 Uiso 0.6 1 calc R . P B 1
H24C H 0.5048 0.1350 0.7518 0.114 Uiso 0.6 1 calc R . P B 1
C22A C 0.613(3) -0.130(2) 0.6942(11) 0.076(2) Uani 0.4 1 d . . P B 2
H22D H 0.6830 -0.0811 0.6664 0.114 Uiso 0.4 1 calc R . P B 2
H22E H 0.6590 -0.1779 0.7337 0.114 Uiso 0.4 1 calc R . P B 2
H22F H 0.5810 -0.1894 0.6689 0.114 Uiso 0.4 1 calc R . P B 2
C23A C 0.414(3) -0.136(4) 0.7517(14) 0.076(2) Uani 0.4 1 d . . P B 2
H23D H 0.3819 -0.1843 0.7204 0.114 Uiso 0.4 1 calc R . P B 2
H23E H 0.4843 -0.1916 0.7797 0.114 Uiso 0.4 1 calc R . P B 2
H23F H 0.3303 -0.1032 0.7796 0.114 Uiso 0.4 1 calc R . P B 2
C24A C 0.530(2) 0.049(3) 0.7573(11) 0.076(2) Uani 0.4 1 d . . P B 2
H24D H 0.5731 0.1184 0.7283 0.114 Uiso 0.4 1 calc R . P B 2
H24E H 0.4499 0.0861 0.7854 0.114 Uiso 0.4 1 calc R . P B 2
H24F H 0.6039 -0.0023 0.7854 0.114 Uiso 0.4 1 calc R . P B 2
Se5 Se 0.35653(7) 0.55125(8) 0.31910(3) 0.0616(2) Uani 1 1 d . . . . .
Se6 Se 0.57587(7) 0.53270(7) 0.25686(3) 0.0502(2) Uani 1 1 d . . . . .
N5 N 0.2712(5) 0.4976(6) 0.2566(3) 0.0564(16) Uani 1 1 d . . . . .
N6 N 0.4935(5) 0.4779(5) 0.1946(2) 0.0472(14) Uani 1 1 d . . . . .
N13 N -0.1868(8) 0.4002(9) 0.0950(4) 0.120(3) Uani 1 1 d . . . . .
C25 C 0.3570(6) 0.4670(5) 0.2049(3) 0.0329(13) Uani 1 1 d . . . . .
C26 C 0.2908(6) 0.4187(5) 0.1527(3) 0.0326(13) Uani 1 1 d . . . . .
C27 C 0.1430(6) 0.4275(5) 0.1518(3) 0.0405(15) Uani 1 1 d . . . . .
H27 H 0.0809 0.4618 0.1858 0.049 Uiso 1 1 calc R . . . .
C28 C 0.0869(7) 0.3854(6) 0.1005(3) 0.0471(16) Uani 1 1 d . . . . .
C29 C 0.1768(7) 0.3313(6) 0.0517(3) 0.0464(16) Uani 1 1 d . . . . .
H29 H 0.1354 0.3033 0.0169 0.056 Uiso 1 1 calc R . . . .
C30 C 0.3243(7) 0.3178(5) 0.0529(3) 0.0412(15) Uani 1 1 d . . . . .
C31 C 0.3782(6) 0.3629(5) 0.1040(3) 0.0350(14) Uani 1 1 d . . . . .
H31 H 0.4801 0.3552 0.1057 0.042 Uiso 1 1 calc R . . . .
C32 C -0.0661(9) 0.3951(8) 0.0978(4) 0.069(2) Uani 1 1 d . . . . .
C33 C 0.4270(7) 0.2549(6) 0.0025(3) 0.0469(16) Uani 1 1 d . . . . .
C34 C 0.5233(8) 0.1407(7) 0.0391(3) 0.068(2) Uani 1 1 d . . . . .
H34A H 0.5723 0.1699 0.0730 0.103 Uiso 1 1 calc R . . . .
H34B H 0.4636 0.0757 0.0605 0.103 Uiso 1 1 calc R . . . .
H34C H 0.5955 0.1035 0.0074 0.103 Uiso 1 1 calc R . . . .
C35 C 0.5238(8) 0.3500(7) -0.0337(3) 0.070(2) Uani 1 1 d . . . . .
H35A H 0.5755 0.3808 -0.0013 0.105 Uiso 1 1 calc R . . . .
H35B H 0.5938 0.3077 -0.0645 0.105 Uiso 1 1 calc R . . . .
H35C H 0.4646 0.4228 -0.0585 0.105 Uiso 1 1 calc R . . . .
C36 C 0.3509(9) 0.2114(7) -0.0498(4) 0.080(3) Uani 1 1 d . . . . .
H36A H 0.4228 0.1716 -0.0808 0.121 Uiso 1 1 calc R . . . .
H36B H 0.2882 0.1487 -0.0285 0.121 Uiso 1 1 calc R . . . .
H36C H 0.2923 0.2854 -0.0740 0.121 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 Se2 2.3096(10) . ?
Se1 N1 1.782(4) . ?
Se2 N2 1.789(4) . ?
N1 C1 1.328(6) . ?
N2 C1 1.326(6) . ?
N11 C8 1.125(7) . ?
C1 C2 1.475(6) . ?
C2 C3 1.376(7) . ?
C2 C7 1.382(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.400(7) . ?
C4 C5 1.375(8) . ?
C4 C9 1.514(9) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(8) . ?
C6 C7 1.385(7) . ?
C6 C8 1.451(8) . ?
C7 H7 0.9500 . ?
C9 C10 1.521(13) . ?
C9 C11 1.518(12) . ?
C9 C12 1.591(13) . ?
C9 C10A 1.44(3) . ?
C9 C11A 1.42(3) . ?
C9 C12A 1.59(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
Se3 Se4 2.3096(9) . ?
Se3 N3 1.793(4) . ?
Se4 N4 1.805(4) . ?
N3 C13 1.313(6) . ?
N4 C13 1.335(6) . ?
N12 C20 1.133(7) . ?
C13 C14 1.487(6) . ?
C14 C15 1.368(7) . ?
C14 C19 1.391(7) . ?
C15 H15 0.9500 . ?
C15 C16 1.398(7) . ?
C16 C17 1.370(7) . ?
C16 C20 1.438(8) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(8) . ?
C18 C19 1.386(7) . ?
C18 C21 1.527(8) . ?
C19 H19 0.9500 . ?
C21 C22 1.47(2) . ?
C21 C23 1.56(2) . ?
C21 C24 1.553(18) . ?
C21 C22A 1.60(3) . ?
C21 C23A 1.39(4) . ?
C21 C24A 1.47(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C22A H22D 0.9800 . ?
C22A H22E 0.9800 . ?
C22A H22F 0.9800 . ?
C23A H23D 0.9800 . ?
C23A H23E 0.9800 . ?
C23A H23F 0.9800 . ?
C24A H24D 0.9800 . ?
C24A H24E 0.9800 . ?
C24A H24F 0.9800 . ?
Se5 Se6 2.3183(12) . ?
Se5 N5 1.779(5) . ?
Se6 N6 1.767(5) . ?
N5 C25 1.323(7) . ?
N6 C25 1.298(7) . ?
N13 C32 1.132(9) . ?
C25 C26 1.481(7) . ?
C26 C27 1.376(7) . ?
C26 C31 1.384(7) . ?
C27 H27 0.9500 . ?
C27 C28 1.382(8) . ?
C28 C29 1.388(8) . ?
C28 C32 1.428(9) . ?
C29 H29 0.9500 . ?
C29 C30 1.371(8) . ?
C30 C31 1.384(8) . ?
C30 C33 1.514(8) . ?
C31 H31 0.9500 . ?
C33 C34 1.533(9) . ?
C33 C35 1.521(9) . ?
C33 C36 1.507(9) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Se1 Se2 90.56(13) . . ?
N2 Se2 Se1 91.79(14) . . ?
C1 N1 Se1 115.7(3) . . ?
C1 N2 Se2 114.2(4) . . ?
N1 C1 C2 116.2(4) . . ?
N2 C1 N1 127.7(5) . . ?
N2 C1 C2 116.0(5) . . ?
C3 C2 C1 119.5(5) . . ?
C3 C2 C7 119.4(5) . . ?
C7 C2 C1 121.1(5) . . ?
C2 C3 H3 118.5 . . ?
C2 C3 C4 123.1(6) . . ?
C4 C3 H3 118.5 . . ?
C3 C4 C9 121.2(6) . . ?
C5 C4 C3 116.2(6) . . ?
C5 C4 C9 122.6(6) . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.7(6) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C7 121.1(6) . . ?
C5 C6 C8 119.4(5) . . ?
C7 C6 C8 119.5(6) . . ?
C2 C7 C6 118.5(5) . . ?
C2 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
N11 C8 C6 179.8(7) . . ?
C4 C9 C10 111.0(6) . . ?
C4 C9 C11 111.8(7) . . ?
C4 C9 C12 113.8(6) . . ?
C4 C9 C12A 107.6(11) . . ?
C10 C9 C12 104.6(8) . . ?
C11 C9 C10 110.1(8) . . ?
C11 C9 C12 105.2(8) . . ?
C10A C9 C4 104.9(11) . . ?
C10A C9 C12A 107.5(17) . . ?
C11A C9 C4 107.2(12) . . ?
C11A C9 C10A 121.5(19) . . ?
C11A C9 C12A 107.5(17) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C10A H10D 109.5 . . ?
C9 C10A H10E 109.5 . . ?
C9 C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C9 C11A H11D 109.5 . . ?
C9 C11A H11E 109.5 . . ?
C9 C11A H11F 109.5 . . ?
H11D C11A H11E 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
C9 C12A H12D 109.5 . . ?
C9 C12A H12E 109.5 . . ?
C9 C12A H12F 109.5 . . ?
H12D C12A H12E 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
N3 Se3 Se4 90.24(13) . . ?
N4 Se4 Se3 91.91(13) . . ?
C13 N3 Se3 116.3(3) . . ?
C13 N4 Se4 113.7(4) . . ?
N3 C13 N4 127.8(5) . . ?
N3 C13 C14 116.4(4) . . ?
N4 C13 C14 115.8(4) . . ?
C15 C14 C13 120.5(5) . . ?
C15 C14 C19 119.5(5) . . ?
C19 C14 C13 120.0(5) . . ?
C14 C15 H15 120.6 . . ?
C14 C15 C16 118.9(5) . . ?
C16 C15 H15 120.6 . . ?
C15 C16 C20 121.3(5) . . ?
C17 C16 C15 120.7(5) . . ?
C17 C16 C20 118.0(5) . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.6(5) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 C19 116.9(5) . . ?
C17 C18 C21 120.0(5) . . ?
C19 C18 C21 123.1(5) . . ?
C14 C19 H19 118.8 . . ?
C18 C19 C14 122.4(5) . . ?
C18 C19 H19 118.8 . . ?
N12 C20 C16 175.9(7) . . ?
C18 C21 C23 105.5(7) . . ?
C18 C21 C24 109.0(7) . . ?
C18 C21 C22A 104.1(9) . . ?
C22 C21 C18 111.0(8) . . ?
C22 C21 C23 121.4(11) . . ?
C22 C21 C24 110.3(8) . . ?
C24 C21 C23 98.6(11) . . ?
C23A C21 C18 119.0(11) . . ?
C23A C21 C22A 90.1(15) . . ?
C23A C21 C24A 115.5(17) . . ?
C24A C21 C18 115.9(10) . . ?
C24A C21 C22A 107.1(12) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C22A H22D 109.5 . . ?
C21 C22A H22E 109.5 . . ?
C21 C22A H22F 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
C21 C23A H23D 109.5 . . ?
C21 C23A H23E 109.5 . . ?
C21 C23A H23F 109.5 . . ?
H23D C23A H23E 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
C21 C24A H24D 109.5 . . ?
C21 C24A H24E 109.5 . . ?
C21 C24A H24F 109.5 . . ?
H24D C24A H24E 109.5 . . ?
H24D C24A H24F 109.5 . . ?
H24E C24A H24F 109.5 . . ?
N5 Se5 Se6 90.65(17) . . ?
N6 Se6 Se5 90.03(16) . . ?
C25 N5 Se5 115.6(4) . . ?
C25 N6 Se6 117.3(4) . . ?
N5 C25 C26 117.2(5) . . ?
N6 C25 N5 126.4(5) . . ?
N6 C25 C26 116.4(5) . . ?
C27 C26 C25 121.0(5) . . ?
C27 C26 C31 119.1(5) . . ?
C31 C26 C25 119.8(5) . . ?
C26 C27 H27 120.7 . . ?
C26 C27 C28 118.6(6) . . ?
C28 C27 H27 120.7 . . ?
C27 C28 C29 121.1(6) . . ?
C27 C28 C32 119.8(6) . . ?
C29 C28 C32 119.0(6) . . ?
C28 C29 H29 119.5 . . ?
C30 C29 C28 121.1(6) . . ?
C30 C29 H29 119.5 . . ?
C29 C30 C31 116.8(6) . . ?
C29 C30 C33 123.2(6) . . ?
C31 C30 C33 120.0(6) . . ?
C26 C31 C30 123.1(6) . . ?
C26 C31 H31 118.4 . . ?
C30 C31 H31 118.4 . . ?
N13 C32 C28 178.3(9) . . ?
C30 C33 C34 108.7(5) . . ?
C30 C33 C35 109.6(5) . . ?
C35 C33 C34 108.1(6) . . ?
C36 C33 C30 113.3(6) . . ?
C36 C33 C34 110.0(5) . . ?
C36 C33 C35 106.9(6) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se1 Se2 N2 C1 -0.4(4) . . . . ?
Se1 N1 C1 N2 -2.7(7) . . . . ?
Se1 N1 C1 C2 173.6(3) . . . . ?
Se2 Se1 N1 C1 1.7(4) . . . . ?
Se2 N2 C1 N1 2.0(7) . . . . ?
Se2 N2 C1 C2 -174.3(3) . . . . ?
N1 C1 C2 C3 -143.6(5) . . . . ?
N1 C1 C2 C7 34.6(7) . . . . ?
N2 C1 C2 C3 33.1(7) . . . . ?
N2 C1 C2 C7 -148.6(5) . . . . ?
C1 C2 C3 C4 176.7(5) . . . . ?
C1 C2 C7 C6 -178.4(5) . . . . ?
C2 C3 C4 C5 2.6(8) . . . . ?
C2 C3 C4 C9 -175.0(6) . . . . ?
C3 C2 C7 C6 -0.1(8) . . . . ?
C3 C4 C5 C6 -2.0(9) . . . . ?
C3 C4 C9 C10 120.5(8) . . . . ?
C3 C4 C9 C11 -116.2(8) . . . . ?
C3 C4 C9 C12 2.9(10) . . . . ?
C3 C4 C9 C10A 68.8(16) . . . . ?
C3 C4 C9 C11A -61.6(16) . . . . ?
C3 C4 C9 C12A -177.0(13) . . . . ?
C4 C5 C6 C7 0.4(9) . . . . ?
C4 C5 C6 C8 178.5(6) . . . . ?
C5 C4 C9 C10 -57.0(10) . . . . ?
C5 C4 C9 C11 66.4(10) . . . . ?
C5 C4 C9 C12 -174.6(7) . . . . ?
C5 C4 C9 C10A -108.7(16) . . . . ?
C5 C4 C9 C11A 121.0(16) . . . . ?
C5 C4 C9 C12A 5.6(15) . . . . ?
C5 C6 C7 C2 0.7(8) . . . . ?
C7 C2 C3 C4 -1.6(8) . . . . ?
C8 C6 C7 C2 -177.4(5) . . . . ?
C9 C4 C5 C6 175.6(6) . . . . ?
Se3 Se4 N4 C13 1.1(4) . . . . ?
Se3 N3 C13 N4 1.5(8) . . . . ?
Se3 N3 C13 C14 -175.1(3) . . . . ?
Se4 Se3 N3 C13 -0.4(4) . . . . ?
Se4 N4 C13 N3 -1.9(7) . . . . ?
Se4 N4 C13 C14 174.8(3) . . . . ?
N3 C13 C14 C15 15.5(7) . . . . ?
N3 C13 C14 C19 -163.5(5) . . . . ?
N4 C13 C14 C15 -161.6(5) . . . . ?
N4 C13 C14 C19 19.5(7) . . . . ?
C13 C14 C15 C16 -178.6(5) . . . . ?
C13 C14 C19 C18 179.3(5) . . . . ?
C14 C15 C16 C17 -1.2(8) . . . . ?
C14 C15 C16 C20 -178.9(5) . . . . ?
C15 C14 C19 C18 0.4(8) . . . . ?
C15 C16 C17 C18 1.4(9) . . . . ?
C16 C17 C18 C19 -0.7(9) . . . . ?
C16 C17 C18 C21 -178.5(6) . . . . ?
C17 C18 C19 C14 -0.2(8) . . . . ?
C17 C18 C21 C22 78.5(9) . . . . ?
C17 C18 C21 C23 -54.8(12) . . . . ?
C17 C18 C21 C24 -159.8(8) . . . . ?
C17 C18 C21 C22A 53.1(12) . . . . ?
C17 C18 C21 C23A -45.1(18) . . . . ?
C17 C18 C21 C24A 170.4(11) . . . . ?
C19 C14 C15 C16 0.3(8) . . . . ?
C19 C18 C21 C22 -99.1(9) . . . . ?
C19 C18 C21 C23 127.6(11) . . . . ?
C19 C18 C21 C24 22.6(10) . . . . ?
C19 C18 C21 C22A -124.5(11) . . . . ?
C19 C18 C21 C23A 137.3(17) . . . . ?
C19 C18 C21 C24A -7.2(13) . . . . ?
C20 C16 C17 C18 179.2(6) . . . . ?
C21 C18 C19 C14 177.5(6) . . . . ?
Se5 Se6 N6 C25 -0.9(4) . . . . ?
Se5 N5 C25 N6 -3.3(8) . . . . ?
Se5 N5 C25 C26 178.5(4) . . . . ?
Se6 Se5 N5 C25 1.8(5) . . . . ?
Se6 N6 C25 N5 2.8(8) . . . . ?
Se6 N6 C25 C26 -178.9(4) . . . . ?
N5 C25 C26 C27 11.6(8) . . . . ?
N5 C25 C26 C31 -168.0(5) . . . . ?
N6 C25 C26 C27 -166.9(5) . . . . ?
N6 C25 C26 C31 13.6(8) . . . . ?
C25 C26 C27 C28 177.6(5) . . . . ?
C25 C26 C31 C30 -178.8(5) . . . . ?
C26 C27 C28 C29 2.1(9) . . . . ?
C26 C27 C28 C32 -179.1(6) . . . . ?
C27 C26 C31 C30 1.7(8) . . . . ?
C27 C28 C29 C30 0.1(10) . . . . ?
C28 C29 C30 C31 -1.3(9) . . . . ?
C28 C29 C30 C33 177.6(6) . . . . ?
C29 C30 C31 C26 0.5(8) . . . . ?
C29 C30 C33 C34 -121.5(7) . . . . ?
C29 C30 C33 C35 120.5(7) . . . . ?
C29 C30 C33 C36 1.2(8) . . . . ?
C31 C26 C27 C28 -2.9(8) . . . . ?
C31 C30 C33 C34 57.4(7) . . . . ?
C31 C30 C33 C35 -60.7(7) . . . . ?
C31 C30 C33 C36 -180.0(6) . . . . ?
C32 C28 C29 C30 -178.8(6) . . . . ?
C33 C30 C31 C26 -178.5(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    ', Oxygen-sensitive'
####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 1512477'
_audit_update_record             
;
2017-06-19 deposited with the CCDC.
2017-06-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_2                   
;
PROBLEM: Short Inter D...A Contact  Se7    ..  N3      ..       2.88 Ang.
RESPONSE: Yes, there really is a short contact, an intermolecular Se...N  
 contact that is not chemically relatable to a (missed) hydrogen bond. This
 is the shortest of a whole network of intermolecular Se/N contacts ranging
 from 0.35 to 0.58 A less than the sums of the VdWr.
;
_vrf_PLAT230_2                   
;
PROBLEM: Hirshfeld Test Diff for    Se1    --  Se2     ..        8.0 s.u.
RESPONSE: The difference in Se displacement ellipsoids can probably be 
attributed to the strong involvement of Se1 in a short contact with N11 
from a CN group on the next ring, whereas Se2 is more weakly contacted to 
aromatic ring C atoms, and in a very different vector direction in the crystal.
;
# Added during the CSD deposition process: Thursday 27 October 2016 05:06 PM
# end Validation Reply Form

# Shelxl code:rb06025

_audit_creation_date             2016-10-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 4-(3-cyano-5-tertbutyl-phenyl)-3H-1,2,3,5-diselenadiazol-3-yl
;
_chemical_formula_moiety         'C12 H12 N3 Se2'
_chemical_formula_sum            'C12 H12 N3 Se2'
_chemical_formula_weight         356.17
_chemical_melting_point          473
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   21.1972(16)
_cell_length_b                   10.6954(8)
_cell_length_c                   28.994(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.6610(10)
_cell_angle_gamma                90
_cell_volume                     6559.9(9)
_cell_formula_units_Z            20
_cell_measurement_reflns_used    7169
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.24
_cell_measurement_theta_min      2.23
_shelx_estimated_absorpt_T_max   0.662
_shelx_estimated_absorpt_T_min   0.449
_exptl_absorpt_coefficient_mu    5.617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5755
_exptl_absorpt_correction_T_max  0.8995
_exptl_absorpt_process_details   
; 
SADABS (Bruker, 2008)
;
_exptl_special_details           
; 
 A crystal coated in Paratone (TM) oil was mounted on the end of a fine glass
 fibre and cooled in the gas stream of the diffractometer Kryoflex device.
;
# Here insert the crystal faces from the .pcf file
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2.00 0.00 1.00 0.0800
2.00 0.00 -1.00 0.0700
0.00 0.00 1.00 0.0500
0.00 0.00 -1.00 0.0200
-1.00 -2.00 2.00 0.0600
1.00 1.00 2.00 0.0900
1.00 2.00 -2.00 0.0800
-1.00 -1.00 -2.00 0.0600
2.00 -1.00 2.00 0.0900
1.00 -1.00 -1.00 0.0700
-1.00 1.00 1.00 0.0700
0.00 -1.00 2.00 0.0600

_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_description       block
_exptl_crystal_F_000             3460
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            74801
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         28.802
_diffrn_reflns_theta_min         1.654
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.929
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker D8'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
 Bruker ApexII CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 66.06
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                11452
_reflns_number_total             15899
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2008)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.993
_refine_diff_density_min         -0.924
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     800
_refine_ls_number_reflns         15899
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²+8.8058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0817
_refine_special_details          
;
 One of the tBu groups anchored by C21 showed significant disorder and a two-
 part rotational disorder model was developed. Isotropic refinements led to 
 close to 50:50 occupancy, and this was subsequently assigned to the two
 components of the disorder. Despite using EADP and ISOR restraints, the
 C22/C22A component went highly oblate. Thus these two atoms alone were left
 to refine isotropically. This model worekd well and picked up no checCIF
 flags.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uiso(C22) = Uiso(C22A)
3. Rigid body (RIGU) restrains
 C23, C24, C23A, C24A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: C22(0.5) H22A(0.5) H22B(0.5) H22C(0.5) C23(0.5) H23A(0.5)
 H23B(0.5) H23C(0.5) C24(0.5) H24A(0.5) H24B(0.5) H24C(0.5) C22A(0.5) H22D(0.5)
 H22E(0.5) H22F(0.5) C23A(0.5) H23D(0.5) H23E(0.5) H23F(0.5) C24A(0.5)
 H24D(0.5) H24E(0.5) H24F(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C51(H51), C53(H53), C55(H55), C39(H39), C41(H41),
 C43(H43), C15(H15), C17(H17), C19(H19), C27(H27), C29(H29), C31(H31)
5.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C58(H58A,H58B,
 H58C), C59(H59A,H59B,H59C), C60(H60A,H60B,H60C), C46(H46A,H46B,H46C), C47(H47A,
 H47B,H47C), C48(H48A,H48B,H48C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C),
 C24(H24A,H24B,H24C), C22A(H22D,H22E,H22F), C23A(H23D,H23E,H23F), C24A(H24D,
 H24E,H24F), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.08769(2) 0.31370(4) 1.03946(2) 0.03601(10) Uani 1 1 d . . . . .
Se2 Se 0.11871(2) 0.26253(4) 0.96597(2) 0.04622(12) Uani 1 1 d . . . . .
N1 N 0.08136(16) 0.4744(3) 1.02342(11) 0.0356(8) Uani 1 1 d . . . . .
N2 N 0.10920(16) 0.4197(3) 0.94890(12) 0.0390(9) Uani 1 1 d . . . . .
N11 N 0.0924(2) 1.0324(4) 1.04755(15) 0.0564(11) Uani 1 1 d . . . . .
C1 C 0.09377(18) 0.5011(3) 0.97996(13) 0.0283(8) Uani 1 1 d . . . . .
C2 C 0.08772(17) 0.6364(4) 0.96645(13) 0.0273(8) Uani 1 1 d . . . . .
C3 C 0.09161(17) 0.7269(4) 1.00064(13) 0.0290(9) Uani 1 1 d . . . . .
H3 H 0.0994 0.7046 1.0322 0.035 Uiso 1 1 calc R . . . .
C4 C 0.08379(18) 0.8526(4) 0.98736(14) 0.0320(9) Uani 1 1 d . . . . .
C5 C 0.07017(19) 0.8859(4) 0.94128(15) 0.0366(10) Uani 1 1 d . . . . .
H5 H 0.0639 0.9714 0.9333 0.044 Uiso 1 1 calc R . . . .
C6 C 0.06575(18) 0.7951(4) 0.90684(14) 0.0344(9) Uani 1 1 d . . . . .
C7 C 0.07554(18) 0.6713(4) 0.92025(14) 0.0327(9) Uani 1 1 d . . . . .
H7 H 0.0739 0.6081 0.8972 0.039 Uiso 1 1 calc R . . . .
C8 C 0.0885(2) 0.9498(4) 1.02138(15) 0.0394(10) Uani 1 1 d . . . . .
C9 C 0.0475(2) 0.8339(4) 0.85634(15) 0.0438(11) Uani 1 1 d . . . . .
C10 C -0.0244(3) 0.8478(7) 0.8518(2) 0.094(2) Uani 1 1 d . . . . .
H10A H -0.0373 0.8808 0.8211 0.141 Uiso 1 1 calc GR . . . .
H10B H -0.0378 0.9057 0.8755 0.141 Uiso 1 1 calc GR . . . .
H10C H -0.0442 0.7661 0.8558 0.141 Uiso 1 1 calc GR . . . .
C11 C 0.0770(3) 0.9578(6) 0.8446(2) 0.0795(19) Uani 1 1 d . . . . .
H11A H 0.1231 0.9517 0.8493 0.119 Uiso 1 1 calc GR . . . .
H11B H 0.0615 1.0233 0.8647 0.119 Uiso 1 1 calc GR . . . .
H11C H 0.0655 0.9788 0.8123 0.119 Uiso 1 1 calc GR . . . .
C12 C 0.0708(4) 0.7372(6) 0.82357(18) 0.112(3) Uani 1 1 d . . . . .
H12A H 0.0630 0.7664 0.7917 0.168 Uiso 1 1 calc GR . . . .
H12B H 0.0483 0.6583 0.8276 0.168 Uiso 1 1 calc GR . . . .
H12C H 0.1162 0.7240 0.8302 0.168 Uiso 1 1 calc GR . . . .
Se9 Se 0.40237(2) 0.64323(3) 0.48194(2) 0.02501(9) Uani 1 1 d . . . . .
Se10 Se 0.41190(2) 0.69442(3) 0.40458(2) 0.02403(8) Uani 1 1 d . . . . .
N9 N 0.40806(15) 0.4801(3) 0.46859(10) 0.0247(7) Uani 1 1 d . . . . .
N10 N 0.41771(14) 0.5332(3) 0.38874(10) 0.0237(7) Uani 1 1 d . . . . .
N15 N 0.42309(18) -0.0827(3) 0.49046(12) 0.0402(9) Uani 1 1 d . . . . .
C49 C 0.41460(16) 0.4538(3) 0.42402(11) 0.0193(7) Uani 1 1 d . . . . .
C50 C 0.41935(16) 0.3176(3) 0.41152(11) 0.0202(7) Uani 1 1 d . . . . .
C51 C 0.42139(17) 0.2246(3) 0.44567(12) 0.0234(8) Uani 1 1 d . . . . .
H51 H 0.4211 0.2461 0.4774 0.028 Uiso 1 1 calc R . . . .
C52 C 0.42385(17) 0.1009(3) 0.43204(12) 0.0241(8) Uani 1 1 d . . . . .
C53 C 0.42433(17) 0.0675(3) 0.38535(12) 0.0228(8) Uani 1 1 d . . . . .
H53 H 0.4255 -0.0183 0.3770 0.027 Uiso 1 1 calc R . . . .
C54 C 0.42314(17) 0.1587(3) 0.35120(12) 0.0233(8) Uani 1 1 d . . . . .
C55 C 0.41995(17) 0.2834(3) 0.36525(12) 0.0237(8) Uani 1 1 d . . . . .
H55 H 0.4181 0.3472 0.3424 0.028 Uiso 1 1 calc R . . . .
C56 C 0.42412(19) 0.0006(3) 0.46590(13) 0.0272(8) Uani 1 1 d . . . . .
C57 C 0.42287(18) 0.1263(3) 0.29941(12) 0.0272(8) Uani 1 1 d . . . . .
C58 C 0.4389(3) -0.0107(5) 0.29163(16) 0.0747(19) Uani 1 1 d . . . . .
H58A H 0.4089 -0.0638 0.3070 0.112 Uiso 1 1 calc GR . . . .
H58B H 0.4819 -0.0278 0.3045 0.112 Uiso 1 1 calc GR . . . .
H58C H 0.4361 -0.0286 0.2584 0.112 Uiso 1 1 calc GR . . . .
C59 C 0.3577(2) 0.1541(6) 0.27684(15) 0.0612(16) Uani 1 1 d . . . . .
H59A H 0.3260 0.1046 0.2919 0.092 Uiso 1 1 calc GR . . . .
H59B H 0.3568 0.1323 0.2440 0.092 Uiso 1 1 calc GR . . . .
H59C H 0.3483 0.2432 0.2801 0.092 Uiso 1 1 calc GR . . . .
C60 C 0.4724(2) 0.2045(5) 0.27663(14) 0.0484(12) Uani 1 1 d . . . . .
H60A H 0.4717 0.1841 0.2437 0.073 Uiso 1 1 calc GR . . . .
H60B H 0.5143 0.1862 0.2912 0.073 Uiso 1 1 calc GR . . . .
H60C H 0.4629 0.2935 0.2804 0.073 Uiso 1 1 calc GR . . . .
Se7 Se 0.25171(2) 0.62897(3) 0.45974(2) 0.02268(8) Uani 1 1 d . . . . .
Se8 Se 0.25943(2) 0.69048(3) 0.38300(2) 0.02691(9) Uani 1 1 d . . . . .
N7 N 0.24809(14) 0.4680(3) 0.44200(10) 0.0246(7) Uani 1 1 d . . . . .
N8 N 0.25475(15) 0.5317(3) 0.36277(10) 0.0260(7) Uani 1 1 d . . . . .
N14 N 0.2685(2) -0.0940(3) 0.44970(14) 0.0538(11) Uani 1 1 d . . . . .
C37 C 0.24959(17) 0.4484(3) 0.39652(12) 0.0219(7) Uani 1 1 d . . . . .
C38 C 0.24112(17) 0.3148(3) 0.38090(12) 0.0229(8) Uani 1 1 d . . . . .
C39 C 0.25748(17) 0.2174(3) 0.41053(13) 0.0251(8) Uani 1 1 d . . . . .
H39 H 0.2771 0.2333 0.4403 0.030 Uiso 1 1 calc R . . . .
C40 C 0.24464(17) 0.0952(3) 0.39591(13) 0.0256(8) Uani 1 1 d . . . . .
C41 C 0.21573(18) 0.0710(3) 0.35196(13) 0.0286(8) Uani 1 1 d . . . . .
H41 H 0.2072 -0.0130 0.3429 0.034 Uiso 1 1 calc R . . . .
C42 C 0.19933(17) 0.1677(3) 0.32149(12) 0.0260(8) Uani 1 1 d . . . . .
C43 C 0.21284(17) 0.2893(3) 0.33700(13) 0.0271(8) Uani 1 1 d . . . . .
H43 H 0.2024 0.3573 0.3169 0.032 Uiso 1 1 calc R . . . .
C44 C 0.2588(2) -0.0097(4) 0.42648(15) 0.0372(10) Uani 1 1 d . . . . .
C45 C 0.1634(2) 0.1417(4) 0.27463(14) 0.0360(10) Uani 1 1 d . . . . .
C46 C 0.1755(3) 0.2393(5) 0.23935(17) 0.0758(19) Uani 1 1 d . . . . .
H46A H 0.1572 0.2125 0.2091 0.114 Uiso 1 1 calc GR . . . .
H46B H 0.2212 0.2510 0.2379 0.114 Uiso 1 1 calc GR . . . .
H46C H 0.1561 0.3183 0.2480 0.114 Uiso 1 1 calc GR . . . .
C47 C 0.0953(2) 0.1222(7) 0.28287(19) 0.092(3) Uani 1 1 d . . . . .
H47A H 0.0754 0.2031 0.2883 0.138 Uiso 1 1 calc GR . . . .
H47B H 0.0918 0.0685 0.3100 0.138 Uiso 1 1 calc GR . . . .
H47C H 0.0740 0.0823 0.2557 0.138 Uiso 1 1 calc GR . . . .
C48 C 0.1876(3) 0.0171(5) 0.25344(18) 0.0715(17) Uani 1 1 d . . . . .
H48A H 0.1688 0.0073 0.2219 0.107 Uiso 1 1 calc GR . . . .
H48B H 0.1753 -0.0538 0.2723 0.107 Uiso 1 1 calc GR . . . .
H48C H 0.2337 0.0198 0.2529 0.107 Uiso 1 1 calc GR . . . .
Se3 Se 0.27745(2) 0.34660(3) 0.53797(2) 0.02459(9) Uani 1 1 d . . . . .
Se4 Se 0.25429(2) 0.29618(3) 0.61336(2) 0.02882(9) Uani 1 1 d . . . . .
N3 N 0.26105(14) 0.5071(3) 0.54836(10) 0.0243(7) Uani 1 1 d . . . . .
N4 N 0.23535(15) 0.4561(3) 0.62547(10) 0.0281(7) Uani 1 1 d . . . . .
N12 N 0.28025(18) 1.0748(3) 0.54502(13) 0.0448(9) Uani 1 1 d . . . . .
C13 C 0.24133(17) 0.5336(3) 0.59033(12) 0.0230(8) Uani 1 1 d . . . . .
C14 C 0.22047(17) 0.6652(3) 0.59713(12) 0.0227(8) Uani 1 1 d . . . . .
C15 C 0.24952(17) 0.7644(3) 0.57525(12) 0.0214(7) Uani 1 1 d . . . . .
H15 H 0.2835 0.7495 0.5561 0.026 Uiso 1 1 calc R . . . .
C16 C 0.22783(18) 0.8845(3) 0.58198(12) 0.0259(8) Uani 1 1 d . . . . .
C17 C 0.17698(17) 0.9078(3) 0.60899(13) 0.0278(8) Uani 1 1 d . . . . .
H17 H 0.1631 0.9912 0.6131 0.033 Uiso 1 1 calc R . . . .
C18 C 0.14616(17) 0.8093(4) 0.63010(13) 0.0296(9) Uani 1 1 d . . . . .
C19 C 0.16968(17) 0.6897(3) 0.62403(12) 0.0266(8) Uani 1 1 d . . . . .
H19 H 0.1504 0.6217 0.6388 0.032 Uiso 1 1 calc R . . . .
C20 C 0.25736(19) 0.9894(3) 0.56062(13) 0.0298(9) Uani 1 1 d . . . . .
C21 C 0.08592(19) 0.8320(4) 0.65573(15) 0.0375(10) Uani 1 1 d . . . . .
C22 C 0.0682(4) 0.7124(9) 0.6877(3) 0.0414(16) Uiso 0.5 1 d . U P A 1
H22A H 0.0625 0.6378 0.6682 0.062 Uiso 0.5 1 calc GR . P A 1
H22B H 0.0289 0.7298 0.7026 0.062 Uiso 0.5 1 calc GR . P A 1
H22C H 0.1025 0.6979 0.7114 0.062 Uiso 0.5 1 calc GR . P A 1
C23 C 0.0943(6) 0.9410(11) 0.6915(4) 0.053(3) Uani 0.5 1 d . U P A 1
H23A H 0.1291 0.9213 0.7142 0.080 Uiso 0.5 1 calc GR . P A 1
H23B H 0.0552 0.9515 0.7074 0.080 Uiso 0.5 1 calc GR . P A 1
H23C H 0.1038 1.0186 0.6754 0.080 Uiso 0.5 1 calc GR . P A 1
C24 C 0.0301(11) 0.8527(15) 0.6225(7) 0.056(5) Uani 0.5 1 d . U P A 1
H24A H 0.0391 0.9213 0.6015 0.084 Uiso 0.5 1 calc GR . P A 1
H24B H -0.0068 0.8740 0.6396 0.084 Uiso 0.5 1 calc GR . P A 1
H24C H 0.0214 0.7762 0.6045 0.084 Uiso 0.5 1 calc GR . P A 1
C22A C 0.0870(4) 0.7584(9) 0.6967(3) 0.0414(16) Uiso 0.5 1 d . U P A 2
H22D H 0.0907 0.6698 0.6887 0.062 Uiso 0.5 1 calc GR . P A 2
H22E H 0.0478 0.7718 0.7122 0.062 Uiso 0.5 1 calc GR . P A 2
H22F H 0.1232 0.7829 0.7174 0.062 Uiso 0.5 1 calc GR . P A 2
C23A C 0.0760(6) 0.9748(11) 0.6632(5) 0.063(3) Uani 0.5 1 d . U P A 2
H23D H 0.1129 1.0094 0.6810 0.095 Uiso 0.5 1 calc GR . P A 2
H23E H 0.0381 0.9880 0.6802 0.095 Uiso 0.5 1 calc GR . P A 2
H23F H 0.0709 1.0167 0.6332 0.095 Uiso 0.5 1 calc GR . P A 2
C24A C 0.0287(12) 0.7941(14) 0.6208(9) 0.056(5) Uani 0.5 1 d . U P A 2
H24D H 0.0280 0.8489 0.5936 0.083 Uiso 0.5 1 calc GR . P A 2
H24E H -0.0110 0.8029 0.6359 0.083 Uiso 0.5 1 calc GR . P A 2
H24F H 0.0338 0.7071 0.6110 0.083 Uiso 0.5 1 calc GR . P A 2
Se5 Se 0.42190(2) 0.38349(3) 0.56563(2) 0.02066(8) Uani 1 1 d . . . . .
Se6 Se 0.41338(2) 0.32947(3) 0.64274(2) 0.02698(9) Uani 1 1 d . . . . .
N5 N 0.40943(13) 0.5444(2) 0.57874(9) 0.0198(6) Uani 1 1 d . . . . .
N6 N 0.40053(15) 0.4889(3) 0.65842(10) 0.0275(7) Uani 1 1 d . . . . .
N13 N 0.44089(16) 1.1121(3) 0.57672(12) 0.0348(8) Uani 1 1 d . . . . .
C25 C 0.40069(17) 0.5696(3) 0.62318(11) 0.0209(7) Uani 1 1 d . . . . .
C26 C 0.39051(16) 0.7030(3) 0.63551(11) 0.0197(7) Uani 1 1 d . . . . .
C27 C 0.41144(16) 0.7992(3) 0.60785(12) 0.0210(7) Uani 1 1 d . . . . .
H27 H 0.4323 0.7816 0.5805 0.025 Uiso 1 1 calc R . . . .
C28 C 0.40087(16) 0.9219(3) 0.62139(12) 0.0210(7) Uani 1 1 d . . . . .
C29 C 0.36998(17) 0.9495(3) 0.66103(12) 0.0250(8) Uani 1 1 d . . . . .
H29 H 0.3634 1.0343 0.6693 0.030 Uiso 1 1 calc R . . . .
C30 C 0.34835(17) 0.8535(3) 0.68905(12) 0.0231(8) Uani 1 1 d . . . . .
C31 C 0.35977(16) 0.7313(3) 0.67511(11) 0.0211(7) Uani 1 1 d . . . . .
H31 H 0.3459 0.6644 0.6935 0.025 Uiso 1 1 calc R . . . .
C32 C 0.42336(18) 1.0264(3) 0.59523(12) 0.0255(8) Uani 1 1 d . . . . .
C33 C 0.31813(18) 0.8826(3) 0.73424(13) 0.0285(8) Uani 1 1 d . . . . .
C34 C 0.2742(2) 0.7779(5) 0.74757(17) 0.0594(15) Uani 1 1 d . . . . .
H34A H 0.2446 0.7581 0.7213 0.089 Uiso 1 1 calc GR . . . .
H34B H 0.2506 0.8046 0.7738 0.089 Uiso 1 1 calc GR . . . .
H34C H 0.2992 0.7034 0.7562 0.089 Uiso 1 1 calc GR . . . .
C35 C 0.2777(3) 1.0008(5) 0.72941(17) 0.0641(16) Uani 1 1 d . . . . .
H35A H 0.3045 1.0720 0.7222 0.096 Uiso 1 1 calc GR . . . .
H35B H 0.2579 1.0168 0.7585 0.096 Uiso 1 1 calc GR . . . .
H35C H 0.2448 0.9895 0.7044 0.096 Uiso 1 1 calc GR . . . .
C36 C 0.3703(2) 0.9005(6) 0.77220(15) 0.0585(15) Uani 1 1 d . . . . .
H36A H 0.3929 0.8214 0.7777 0.088 Uiso 1 1 calc GR . . . .
H36B H 0.3518 0.9272 0.8007 0.088 Uiso 1 1 calc GR . . . .
H36C H 0.4000 0.9645 0.7627 0.088 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 Se2 2.3347(6) . ?
Se1 N1 1.783(3) . ?
Se2 N2 1.760(4) . ?
N1 C1 1.335(5) . ?
N2 C1 1.309(5) . ?
N11 C8 1.164(5) . ?
C1 C2 1.502(5) . ?
C2 C3 1.384(5) . ?
C2 C7 1.399(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.406(5) . ?
C4 C5 1.395(6) . ?
C4 C8 1.432(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(6) . ?
C6 C7 1.392(6) . ?
C6 C9 1.547(6) . ?
C7 H7 0.9500 . ?
C9 C10 1.528(7) . ?
C9 C11 1.514(7) . ?
C9 C12 1.509(7) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
Se9 Se10 2.3299(5) . ?
Se9 N9 1.792(3) . ?
Se10 N10 1.791(3) . ?
N9 C49 1.339(4) . ?
N10 C49 1.334(4) . ?
N15 C56 1.142(5) . ?
C49 C50 1.506(4) . ?
C50 C51 1.402(5) . ?
C50 C55 1.391(5) . ?
C51 H51 0.9500 . ?
C51 C52 1.383(5) . ?
C52 C53 1.401(5) . ?
C52 C56 1.454(5) . ?
C53 H53 0.9500 . ?
C53 C54 1.389(5) . ?
C54 C55 1.398(5) . ?
C54 C57 1.540(5) . ?
C55 H55 0.9500 . ?
C57 C58 1.524(6) . ?
C57 C59 1.520(6) . ?
C57 C60 1.525(6) . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C59 H59A 0.9800 . ?
C59 H59B 0.9800 . ?
C59 H59C 0.9800 . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 0.9800 . ?
Se7 Se8 2.3360(5) . ?
Se7 N7 1.797(3) . ?
Se8 N8 1.797(3) . ?
N7 C37 1.338(4) . ?
N8 C37 1.333(4) . ?
N14 C44 1.137(5) . ?
C37 C38 1.506(5) . ?
C38 C39 1.381(5) . ?
C38 C43 1.399(5) . ?
C39 H39 0.9500 . ?
C39 C40 1.396(5) . ?
C40 C41 1.402(5) . ?
C40 C44 1.449(5) . ?
C41 H41 0.9500 . ?
C41 C42 1.390(5) . ?
C42 C43 1.400(5) . ?
C42 C45 1.540(5) . ?
C43 H43 0.9500 . ?
C45 C46 1.495(6) . ?
C45 C47 1.492(6) . ?
C45 C48 1.567(6) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
Se3 Se4 2.3337(5) . ?
Se3 N3 1.781(3) . ?
Se4 N4 1.797(3) . ?
N3 C13 1.342(4) . ?
N4 C13 1.326(4) . ?
N12 C20 1.141(5) . ?
C13 C14 1.493(5) . ?
C14 C15 1.398(5) . ?
C14 C19 1.394(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(5) . ?
C16 C17 1.395(5) . ?
C16 C20 1.443(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.401(5) . ?
C18 C19 1.388(5) . ?
C18 C21 1.537(5) . ?
C19 H19 0.9500 . ?
C21 C22 1.638(10) . ?
C21 C23 1.564(11) . ?
C21 C24 1.49(2) . ?
C21 C22A 1.424(10) . ?
C21 C23A 1.558(12) . ?
C21 C24A 1.58(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C22A H22D 0.9800 . ?
C22A H22E 0.9800 . ?
C22A H22F 0.9800 . ?
C23A H23D 0.9800 . ?
C23A H23E 0.9800 . ?
C23A H23F 0.9800 . ?
C24A H24D 0.9800 . ?
C24A H24E 0.9800 . ?
C24A H24F 0.9800 . ?
Se5 Se6 2.3274(5) . ?
Se5 N5 1.786(3) . ?
Se6 N6 1.790(3) . ?
N5 C25 1.341(4) . ?
N6 C25 1.338(4) . ?
N13 C32 1.136(5) . ?
C25 C26 1.489(4) . ?
C26 C27 1.395(5) . ?
C26 C31 1.389(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.392(5) . ?
C28 C29 1.390(5) . ?
C28 C32 1.448(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.405(5) . ?
C30 C31 1.393(5) . ?
C30 C33 1.527(5) . ?
C31 H31 0.9500 . ?
C33 C34 1.521(6) . ?
C33 C35 1.529(6) . ?
C33 C36 1.523(6) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Se1 Se2 90.50(11) . . ?
N2 Se2 Se1 89.93(11) . . ?
C1 N1 Se1 115.9(3) . . ?
C1 N2 Se2 118.1(3) . . ?
N1 C1 C2 115.7(3) . . ?
N2 C1 N1 125.4(4) . . ?
N2 C1 C2 118.8(4) . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 C7 119.9(4) . . ?
C7 C2 C1 120.9(3) . . ?
C2 C3 H3 120.9 . . ?
C2 C3 C4 118.2(4) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 C8 120.3(4) . . ?
C5 C4 C3 121.3(4) . . ?
C5 C4 C8 118.4(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(4) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C9 119.5(4) . . ?
C7 C6 C5 117.5(4) . . ?
C7 C6 C9 122.9(4) . . ?
C2 C7 H7 118.8 . . ?
C6 C7 C2 122.4(4) . . ?
C6 C7 H7 118.8 . . ?
N11 C8 C4 177.2(5) . . ?
C10 C9 C6 107.3(4) . . ?
C11 C9 C6 111.4(4) . . ?
C11 C9 C10 108.6(5) . . ?
C12 C9 C6 109.9(4) . . ?
C12 C9 C10 112.2(5) . . ?
C12 C9 C11 107.6(5) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N9 Se9 Se10 90.56(9) . . ?
N10 Se10 Se9 91.85(9) . . ?
C49 N9 Se9 115.2(2) . . ?
C49 N10 Se10 114.1(2) . . ?
N9 C49 C50 116.7(3) . . ?
N10 C49 N9 128.3(3) . . ?
N10 C49 C50 115.1(3) . . ?
C51 C50 C49 121.0(3) . . ?
C55 C50 C49 119.4(3) . . ?
C55 C50 C51 119.5(3) . . ?
C50 C51 H51 120.8 . . ?
C52 C51 C50 118.5(3) . . ?
C52 C51 H51 120.8 . . ?
C51 C52 C53 121.5(3) . . ?
C51 C52 C56 120.8(3) . . ?
C53 C52 C56 117.7(3) . . ?
C52 C53 H53 119.7 . . ?
C54 C53 C52 120.6(3) . . ?
C54 C53 H53 119.7 . . ?
C53 C54 C55 117.5(3) . . ?
C53 C54 C57 122.4(3) . . ?
C55 C54 C57 120.1(3) . . ?
C50 C55 C54 122.4(3) . . ?
C50 C55 H55 118.8 . . ?
C54 C55 H55 118.8 . . ?
N15 C56 C52 176.0(4) . . ?
C58 C57 C54 111.9(3) . . ?
C58 C57 C60 107.3(4) . . ?
C59 C57 C54 108.8(3) . . ?
C59 C57 C58 109.2(4) . . ?
C59 C57 C60 109.8(4) . . ?
C60 C57 C54 109.8(3) . . ?
C57 C58 H58A 109.5 . . ?
C57 C58 H58B 109.5 . . ?
C57 C58 H58C 109.5 . . ?
H58A C58 H58B 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C57 C59 H59A 109.5 . . ?
C57 C59 H59B 109.5 . . ?
C57 C59 H59C 109.5 . . ?
H59A C59 H59B 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
C57 C60 H60A 109.5 . . ?
C57 C60 H60B 109.5 . . ?
C57 C60 H60C 109.5 . . ?
H60A C60 H60B 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
N7 Se7 Se8 90.09(9) . . ?
N8 Se8 Se7 92.23(9) . . ?
C37 N7 Se7 115.4(2) . . ?
C37 N8 Se8 113.4(2) . . ?
N7 C37 C38 115.8(3) . . ?
N8 C37 N7 128.9(3) . . ?
N8 C37 C38 115.3(3) . . ?
C39 C38 C37 120.6(3) . . ?
C39 C38 C43 119.7(3) . . ?
C43 C38 C37 119.7(3) . . ?
C38 C39 H39 120.6 . . ?
C38 C39 C40 118.8(3) . . ?
C40 C39 H39 120.6 . . ?
C39 C40 C41 121.0(3) . . ?
C39 C40 C44 120.7(3) . . ?
C41 C40 C44 118.3(3) . . ?
C40 C41 H41 119.4 . . ?
C42 C41 C40 121.1(3) . . ?
C42 C41 H41 119.4 . . ?
C41 C42 C43 116.7(3) . . ?
C41 C42 C45 121.0(3) . . ?
C43 C42 C45 122.1(3) . . ?
C38 C43 C42 122.7(3) . . ?
C38 C43 H43 118.6 . . ?
C42 C43 H43 118.6 . . ?
N14 C44 C40 177.8(5) . . ?
C42 C45 C48 110.1(4) . . ?
C46 C45 C42 112.3(3) . . ?
C46 C45 C48 104.5(4) . . ?
C47 C45 C42 108.2(4) . . ?
C47 C45 C46 114.7(5) . . ?
C47 C45 C48 106.8(4) . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C45 C47 H47A 109.5 . . ?
C45 C47 H47B 109.5 . . ?
C45 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
N3 Se3 Se4 90.54(9) . . ?
N4 Se4 Se3 91.49(10) . . ?
C13 N3 Se3 115.6(2) . . ?
C13 N4 Se4 114.3(2) . . ?
N3 C13 C14 115.5(3) . . ?
N4 C13 N3 128.0(3) . . ?
N4 C13 C14 116.4(3) . . ?
C15 C14 C13 120.8(3) . . ?
C19 C14 C13 119.8(3) . . ?
C19 C14 C15 119.3(3) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 C14 118.7(3) . . ?
C16 C15 H15 120.6 . . ?
C15 C16 C17 121.4(3) . . ?
C15 C16 C20 120.3(3) . . ?
C17 C16 C20 118.3(3) . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.7(3) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C21 121.1(3) . . ?
C19 C18 C17 117.1(3) . . ?
C19 C18 C21 121.6(4) . . ?
C14 C19 H19 118.6 . . ?
C18 C19 C14 122.7(4) . . ?
C18 C19 H19 118.6 . . ?
N12 C20 C16 177.6(4) . . ?
C18 C21 C22 112.2(4) . . ?
C18 C21 C23 112.1(5) . . ?
C18 C21 C23A 110.2(5) . . ?
C18 C21 C24A 106.0(9) . . ?
C23 C21 C22 103.1(6) . . ?
C24 C21 C18 111.1(9) . . ?
C24 C21 C22 106.3(8) . . ?
C24 C21 C23 111.7(9) . . ?
C22A C21 C18 110.3(5) . . ?
C22A C21 C23A 114.9(7) . . ?
C22A C21 C24A 111.3(9) . . ?
C23A C21 C24A 103.6(8) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C22A H22D 109.5 . . ?
C21 C22A H22E 109.5 . . ?
C21 C22A H22F 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
C21 C23A H23D 109.5 . . ?
C21 C23A H23E 109.5 . . ?
C21 C23A H23F 109.5 . . ?
H23D C23A H23E 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
C21 C24A H24D 109.5 . . ?
C21 C24A H24E 109.5 . . ?
C21 C24A H24F 109.5 . . ?
H24D C24A H24E 109.5 . . ?
H24D C24A H24F 109.5 . . ?
H24E C24A H24F 109.5 . . ?
N5 Se5 Se6 90.76(9) . . ?
N6 Se6 Se5 91.71(9) . . ?
C25 N5 Se5 115.5(2) . . ?
C25 N6 Se6 114.4(2) . . ?
N5 C25 C26 117.0(3) . . ?
N6 C25 N5 127.7(3) . . ?
N6 C25 C26 115.3(3) . . ?
C27 C26 C25 120.8(3) . . ?
C31 C26 C25 119.4(3) . . ?
C31 C26 C27 119.8(3) . . ?
C26 C27 H27 121.0 . . ?
C28 C27 C26 118.1(3) . . ?
C28 C27 H27 121.0 . . ?
C27 C28 C32 121.0(3) . . ?
C29 C28 C27 121.7(3) . . ?
C29 C28 C32 117.2(3) . . ?
C28 C29 H29 119.6 . . ?
C28 C29 C30 120.8(3) . . ?
C30 C29 H29 119.6 . . ?
C29 C30 C33 121.2(3) . . ?
C31 C30 C29 116.7(3) . . ?
C31 C30 C33 122.0(3) . . ?
C26 C31 C30 122.9(3) . . ?
C26 C31 H31 118.5 . . ?
C30 C31 H31 118.5 . . ?
N13 C32 C28 176.5(4) . . ?
C30 C33 C35 110.7(3) . . ?
C34 C33 C30 111.4(3) . . ?
C34 C33 C35 106.5(4) . . ?
C34 C33 C36 109.7(4) . . ?
C36 C33 C30 108.7(3) . . ?
C36 C33 C35 109.8(4) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se1 Se2 N2 C1 3.5(3) . . . . ?
Se1 N1 C1 N2 0.8(5) . . . . ?
Se1 N1 C1 C2 179.4(3) . . . . ?
Se2 Se1 N1 C1 1.5(3) . . . . ?
Se2 N2 C1 N1 -3.6(6) . . . . ?
Se2 N2 C1 C2 177.9(3) . . . . ?
N1 C1 C2 C3 21.8(5) . . . . ?
N1 C1 C2 C7 -155.4(4) . . . . ?
N2 C1 C2 C3 -159.5(4) . . . . ?
N2 C1 C2 C7 23.3(6) . . . . ?
C1 C2 C3 C4 -178.0(3) . . . . ?
C1 C2 C7 C6 175.9(4) . . . . ?
C2 C3 C4 C5 2.3(6) . . . . ?
C2 C3 C4 C8 -179.0(4) . . . . ?
C3 C2 C7 C6 -1.3(6) . . . . ?
C3 C4 C5 C6 -1.9(6) . . . . ?
C4 C5 C6 C7 -0.1(6) . . . . ?
C4 C5 C6 C9 177.1(4) . . . . ?
C5 C6 C7 C2 1.7(6) . . . . ?
C5 C6 C9 C10 -80.9(5) . . . . ?
C5 C6 C9 C11 37.8(6) . . . . ?
C5 C6 C9 C12 156.9(5) . . . . ?
C7 C2 C3 C4 -0.8(6) . . . . ?
C7 C6 C9 C10 96.2(5) . . . . ?
C7 C6 C9 C11 -145.1(5) . . . . ?
C7 C6 C9 C12 -26.0(6) . . . . ?
C8 C4 C5 C6 179.4(4) . . . . ?
C9 C6 C7 C2 -175.4(4) . . . . ?
Se9 Se10 N10 C49 0.0(3) . . . . ?
Se9 N9 C49 N10 0.4(5) . . . . ?
Se9 N9 C49 C50 -179.8(2) . . . . ?
Se10 Se9 N9 C49 -0.3(3) . . . . ?
Se10 N10 C49 N9 -0.3(5) . . . . ?
Se10 N10 C49 C50 180.0(2) . . . . ?
N9 C49 C50 C51 -4.5(5) . . . . ?
N9 C49 C50 C55 173.7(3) . . . . ?
N10 C49 C50 C51 175.3(3) . . . . ?
N10 C49 C50 C55 -6.5(5) . . . . ?
C49 C50 C51 C52 178.1(3) . . . . ?
C49 C50 C55 C54 -178.8(3) . . . . ?
C50 C51 C52 C53 0.0(6) . . . . ?
C50 C51 C52 C56 -178.1(3) . . . . ?
C51 C50 C55 C54 -0.6(5) . . . . ?
C51 C52 C53 C54 0.8(6) . . . . ?
C52 C53 C54 C55 -1.5(5) . . . . ?
C52 C53 C54 C57 -179.3(3) . . . . ?
C53 C54 C55 C50 1.4(5) . . . . ?
C53 C54 C57 C58 -12.8(5) . . . . ?
C53 C54 C57 C59 107.9(4) . . . . ?
C53 C54 C57 C60 -131.9(4) . . . . ?
C55 C50 C51 C52 -0.1(5) . . . . ?
C55 C54 C57 C58 169.4(4) . . . . ?
C55 C54 C57 C59 -69.9(5) . . . . ?
C55 C54 C57 C60 50.3(5) . . . . ?
C56 C52 C53 C54 179.0(3) . . . . ?
C57 C54 C55 C50 179.3(3) . . . . ?
Se7 Se8 N8 C37 -0.4(3) . . . . ?
Se7 N7 C37 N8 1.6(5) . . . . ?
Se7 N7 C37 C38 -175.1(2) . . . . ?
Se8 Se7 N7 C37 -1.3(3) . . . . ?
Se8 N8 C37 N7 -0.6(5) . . . . ?
Se8 N8 C37 C38 176.1(2) . . . . ?
N7 C37 C38 C39 -26.2(5) . . . . ?
N7 C37 C38 C43 149.9(3) . . . . ?
N8 C37 C38 C39 156.7(3) . . . . ?
N8 C37 C38 C43 -27.3(5) . . . . ?
C37 C38 C39 C40 175.4(3) . . . . ?
C37 C38 C43 C42 -175.3(3) . . . . ?
C38 C39 C40 C41 0.1(5) . . . . ?
C38 C39 C40 C44 -177.7(4) . . . . ?
C39 C38 C43 C42 0.8(5) . . . . ?
C39 C40 C41 C42 0.4(6) . . . . ?
C40 C41 C42 C43 -0.3(5) . . . . ?
C40 C41 C42 C45 -175.6(3) . . . . ?
C41 C42 C43 C38 -0.3(5) . . . . ?
C41 C42 C45 C46 -153.8(4) . . . . ?
C41 C42 C45 C47 78.5(5) . . . . ?
C41 C42 C45 C48 -37.8(5) . . . . ?
C43 C38 C39 C40 -0.7(5) . . . . ?
C43 C42 C45 C46 31.1(6) . . . . ?
C43 C42 C45 C47 -96.6(5) . . . . ?
C43 C42 C45 C48 147.1(4) . . . . ?
C44 C40 C41 C42 178.2(4) . . . . ?
C45 C42 C43 C38 175.0(3) . . . . ?
Se3 Se4 N4 C13 -0.1(3) . . . . ?
Se3 N3 C13 N4 3.3(5) . . . . ?
Se3 N3 C13 C14 -173.2(2) . . . . ?
Se4 Se3 N3 C13 -2.4(3) . . . . ?
Se4 N4 C13 N3 -1.9(5) . . . . ?
Se4 N4 C13 C14 174.5(2) . . . . ?
N3 C13 C14 C15 -33.8(5) . . . . ?
N3 C13 C14 C19 143.5(3) . . . . ?
N4 C13 C14 C15 149.3(3) . . . . ?
N4 C13 C14 C19 -33.4(5) . . . . ?
C13 C14 C15 C16 178.9(3) . . . . ?
C13 C14 C19 C18 -177.1(3) . . . . ?
C14 C15 C16 C17 -1.6(5) . . . . ?
C14 C15 C16 C20 178.9(3) . . . . ?
C15 C14 C19 C18 0.2(5) . . . . ?
C15 C16 C17 C18 -0.2(5) . . . . ?
C16 C17 C18 C19 1.9(5) . . . . ?
C16 C17 C18 C21 -173.6(3) . . . . ?
C17 C18 C19 C14 -1.9(5) . . . . ?
C17 C18 C21 C22 -166.2(5) . . . . ?
C17 C18 C21 C23 -50.7(7) . . . . ?
C17 C18 C21 C24 75.0(8) . . . . ?
C17 C18 C21 C22A -140.3(5) . . . . ?
C17 C18 C21 C23A -12.5(7) . . . . ?
C17 C18 C21 C24A 99.1(7) . . . . ?
C19 C14 C15 C16 1.6(5) . . . . ?
C19 C18 C21 C22 18.5(6) . . . . ?
C19 C18 C21 C23 134.0(6) . . . . ?
C19 C18 C21 C24 -100.3(8) . . . . ?
C19 C18 C21 C22A 44.4(6) . . . . ?
C19 C18 C21 C23A 172.2(6) . . . . ?
C19 C18 C21 C24A -76.2(8) . . . . ?
C20 C16 C17 C18 179.3(3) . . . . ?
C21 C18 C19 C14 173.6(3) . . . . ?
Se5 Se6 N6 C25 0.1(3) . . . . ?
Se5 N5 C25 N6 0.3(5) . . . . ?
Se5 N5 C25 C26 179.7(2) . . . . ?
Se6 Se5 N5 C25 -0.2(2) . . . . ?
Se6 N6 C25 N5 -0.2(5) . . . . ?
Se6 N6 C25 C26 -179.6(2) . . . . ?
N5 C25 C26 C27 -22.8(5) . . . . ?
N5 C25 C26 C31 157.3(3) . . . . ?
N6 C25 C26 C27 156.7(3) . . . . ?
N6 C25 C26 C31 -23.3(5) . . . . ?
C25 C26 C27 C28 -179.6(3) . . . . ?
C25 C26 C31 C30 -180.0(3) . . . . ?
C26 C27 C28 C29 -0.5(5) . . . . ?
C26 C27 C28 C32 177.7(3) . . . . ?
C27 C26 C31 C30 0.1(5) . . . . ?
C27 C28 C29 C30 0.2(5) . . . . ?
C28 C29 C30 C31 0.3(5) . . . . ?
C28 C29 C30 C33 176.1(3) . . . . ?
C29 C30 C31 C26 -0.4(5) . . . . ?
C29 C30 C33 C34 155.3(4) . . . . ?
C29 C30 C33 C35 37.0(5) . . . . ?
C29 C30 C33 C36 -83.7(5) . . . . ?
C31 C26 C27 C28 0.4(5) . . . . ?
C31 C30 C33 C34 -29.1(5) . . . . ?
C31 C30 C33 C35 -147.4(4) . . . . ?
C31 C30 C33 C36 91.9(4) . . . . ?
C32 C28 C29 C30 -178.2(3) . . . . ?
C33 C30 C31 C26 -176.1(3) . . . . ?


# start Validation Reply Form
_vrf_PLAT430_1                   
;
PROBLEM: Short Inter D...A Contact  Se7    ..  N3      ..       2.88 Ang.  
RESPONSE: Yes, there really is a short contact, an intermolecular Se...N 
contact that is NOT chemically relatable to a (missed) hydrogen bond. THis
is the shortest of a whole network of intermolecular Se/N contacts.
;
_vrf_PLAT230_1                   
;
PROBLEM: Hirshfeld Test Diff for    Se1    --  Se2     ..        8.0 s.u.  
RESPONSE: The difference in Se displacement ellipsoids can probably be
attributed to the strong involvement of Se1 in a short contact with N11
from a CN group on the next ring, whereas Se2 is more weakly contacted to
aromatic ring C atoms, and in a very different vector direction in the
crystal.
;
# end Validation Reply Form 

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    ', Oxygen-sensitive'
