# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 1820888'
_audit_update_record             
;
2018-01-31 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;

_audit_creation_date             2017-02-22T09:24:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_sum            'C12 H9 N3 Se3'
_chemical_formula_moiety         'C12 H9 N3 Se3'
_chemical_formula_weight         432.10

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

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

_cell_length_a                   5.9630(2)
_cell_length_b                   23.1856(8)
_cell_length_c                   10.0548(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.046(2)
_cell_angle_gamma                90
_cell_volume                     1388.17(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2739
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      26.3
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    2.068
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816

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

_exptl_absorpt_coefficient_mu    7.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.627
_exptl_absorpt_correction_T_max  0.924

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.5397  0.7456                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------# 
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      0.130423
_diffrn_orient_matrix_ub_12      -0.019356
_diffrn_orient_matrix_ub_13      -0.03986
_diffrn_orient_matrix_ub_21      0.063849
_diffrn_orient_matrix_ub_22      0.038535
_diffrn_orient_matrix_ub_23      -0.021768
_diffrn_orient_matrix_ub_31      0.084359
_diffrn_orient_matrix_ub_32      0.000759
_diffrn_orient_matrix_ub_33      0.088638
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_number            9778
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.757
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             3183
_reflns_number_gt                2299
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0297P)²+5.0843P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3183
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.765
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.12

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


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

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1873(8) 0.6085(2) -0.2010(5) 0.0286(12) Uani 1 1 d . . . . .
C2 C -0.0016(8) 0.5818(3) -0.2603(5) 0.0312(12) Uani 1 1 d . . . . .
H2 H -0.027 0.5429 -0.2447 0.037 Uiso 1 1 calc R U . . .
C3 C -0.1539(8) 0.6129(3) -0.3431(5) 0.0301(12) Uani 1 1 d . . . . .
C4 C -0.1152(9) 0.6702(3) -0.3646(5) 0.0347(13) Uani 1 1 d . . . . .
H4 H -0.2166 0.691 -0.4195 0.042 Uiso 1 1 calc R U . . .
C5 C 0.0712(10) 0.6984(3) -0.3069(6) 0.0360(13) Uani 1 1 d . . . . .
C6 C 0.2220(9) 0.6668(3) -0.2245(5) 0.0346(13) Uani 1 1 d . . . . .
H6 H 0.3473 0.6851 -0.1848 0.042 Uiso 1 1 calc R U . . .
C7 C 0.3532(9) 0.5746(3) -0.1149(5) 0.0353(13) Uani 1 1 d . . . . .
H7A H 0.5037 0.5863 -0.1354 0.042 Uiso 1 1 calc R U . . .
H7B H 0.3373 0.5341 -0.1374 0.042 Uiso 1 1 calc R U . . .
C8 C 0.0130(9) 0.5761(3) 0.0722(5) 0.0382(14) Uani 1 1 d . . . . .
C9 C -0.3474(9) 0.5824(3) -0.4117(5) 0.0396(14) Uani 1 1 d . . . . .
H9A H -0.4843 0.6035 -0.3972 0.047 Uiso 1 1 calc R U . . .
H9B H -0.3617 0.5443 -0.3729 0.047 Uiso 1 1 calc R U . . .
C10 C -0.0023(9) 0.5682(3) -0.5954(6) 0.0386(14) Uani 1 1 d . . . . .
C11 C 0.1140(11) 0.7600(3) -0.3375(7) 0.0498(17) Uani 1 1 d . . . . .
H11A H 0.1645 0.7795 -0.256 0.06 Uiso 1 1 calc R U . . .
H11B H -0.0261 0.7778 -0.3692 0.06 Uiso 1 1 calc R U . . .
C12 C 0.1926(13) 0.7294(3) -0.6019(8) 0.0542(18) Uani 1 1 d . . . . .
N1 N -0.1757(8) 0.5712(3) 0.0720(6) 0.0579(16) Uani 1 1 d . . . . .
N2 N 0.1854(8) 0.5641(3) -0.5938(5) 0.0555(16) Uani 1 1 d . . . . .
N3 N 0.1079(13) 0.7048(3) -0.6880(8) 0.079(2) Uani 1 1 d . . . . .
Se1 Se 0.32033(9) 0.58377(3) 0.07838(5) 0.03854(18) Uani 1 1 d . . . . .
Se2 Se -0.31277(9) 0.57438(3) -0.60634(5) 0.03952(19) Uani 1 1 d . . . . .
Se3 Se 0.33921(14) 0.77190(3) -0.47185(9) 0.0637(3) Uani 1 1 d . . . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.390(8) . ?
C1 C2 1.391(7) . ?
C1 C7 1.501(7) . ?
C2 C3 1.399(7) . ?
C2 H2 0.93 . ?
C3 C4 1.369(8) . ?
C3 C9 1.491(8) . ?
C4 C5 1.389(8) . ?
C4 H4 0.93 . ?
C5 C6 1.397(8) . ?
C5 C11 1.487(8) . ?
C6 H6 0.93 . ?
C7 Se1 1.975(5) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 N1 1.131(7) . ?
C8 Se1 1.839(6) . ?
C9 Se2 1.987(5) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 N2 1.123(7) . ?
C10 Se2 1.854(6) . ?
C11 Se3 1.974(6) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 N3 1.132(9) . ?
C12 Se3 1.823(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.9(5) . . ?
C6 C1 C7 120.5(5) . . ?
C2 C1 C7 120.6(5) . . ?
C1 C2 C3 120.8(5) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 119.0(5) . . ?
C4 C3 C9 121.4(5) . . ?
C2 C3 C9 119.6(5) . . ?
C3 C4 C5 121.9(5) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 118.5(5) . . ?
C4 C5 C11 120.5(6) . . ?
C6 C5 C11 120.9(5) . . ?
C1 C6 C5 120.9(5) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C1 C7 Se1 114.5(4) . . ?
C1 C7 H7A 108.6 . . ?
Se1 C7 H7A 108.6 . . ?
C1 C7 H7B 108.6 . . ?
Se1 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
N1 C8 Se1 178.1(5) . . ?
C3 C9 Se2 112.4(4) . . ?
C3 C9 H9A 109.1 . . ?
Se2 C9 H9A 109.1 . . ?
C3 C9 H9B 109.1 . . ?
Se2 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
N2 C10 Se2 177.3(5) . . ?
C5 C11 Se3 113.9(4) . . ?
C5 C11 H11A 108.8 . . ?
Se3 C11 H11A 108.8 . . ?
C5 C11 H11B 108.8 . . ?
Se3 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
N3 C12 Se3 176.0(7) . . ?
C8 Se1 C7 96.1(2) . . ?
C10 Se2 C9 96.0(2) . . ?
C12 Se3 C11 95.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.4(7) . . . . ?
C7 C1 C2 C3 -178.4(4) . . . . ?
C1 C2 C3 C4 -0.4(7) . . . . ?
C1 C2 C3 C9 176.4(4) . . . . ?
C2 C3 C4 C5 0.2(8) . . . . ?
C9 C3 C4 C5 -176.5(5) . . . . ?
C3 C4 C5 C6 -0.2(8) . . . . ?
C3 C4 C5 C11 177.1(5) . . . . ?
C2 C1 C6 C5 -0.4(8) . . . . ?
C7 C1 C6 C5 178.5(5) . . . . ?
C4 C5 C6 C1 0.3(8) . . . . ?
C11 C5 C6 C1 -177.0(5) . . . . ?
C6 C1 C7 Se1 80.9(6) . . . . ?
C2 C1 C7 Se1 -100.2(5) . . . . ?
C4 C3 C9 Se2 68.4(6) . . . . ?
C2 C3 C9 Se2 -108.3(5) . . . . ?
C4 C5 C11 Se3 -99.7(6) . . . . ?
C6 C5 C11 Se3 77.5(6) . . . . ?

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1820892'
_audit_update_record             
;
2018-01-31 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;

_audit_creation_date             2017-03-08T15:43:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_sum            'C14 H10 N4 Se4'
_chemical_formula_moiety         'C14 H10 N4 Se4'
_chemical_formula_weight         550.1

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

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

_cell_length_a                   5.4173(12)
_cell_length_b                   13.172(3)
_cell_length_c                   11.795(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.451(14)
_cell_angle_gamma                90
_cell_volume                     834.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1197
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      23.14
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    2.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516

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

_exptl_absorpt_coefficient_mu    8.792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_T_max  0.916

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.4858  0.7456                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------#

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

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      -0.152531
_diffrn_orient_matrix_ub_12      -0.034956
_diffrn_orient_matrix_ub_13      0.019876
_diffrn_orient_matrix_ub_21      -0.097579
_diffrn_orient_matrix_ub_22      0.027344
_diffrn_orient_matrix_ub_23      -0.07124
_diffrn_orient_matrix_ub_31      0.043247
_diffrn_orient_matrix_ub_32      -0.061593
_diffrn_orient_matrix_ub_33      -0.042907
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0747
_diffrn_reflns_number            6327
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.329
_diffrn_reflns_theta_max         27.638
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_Friedel_coverage         0
_reflns_number_total             1923
_reflns_number_gt                1281
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'


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

_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0654P)²+0.1321P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1923
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.101
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_restrained_S_all      0.914
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.745
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.14

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


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

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se01 Se 0.83477(11) 0.71862(4) 0.46838(5) 0.0321(2) Uani 1 1 d . . . . .
Se02 Se 0.71372(13) 1.03520(5) 0.17989(5) 0.0424(2) Uani 1 1 d . . . . .
C3 C 0.5249(10) 0.9026(4) 0.4535(4) 0.0247(12) Uani 1 1 d . . . . .
C2 C 0.6572(10) 0.9836(4) 0.4159(4) 0.0241(11) Uani 1 1 d . . . . .
C4 C 0.8313(10) 0.9712(4) 0.3276(4) 0.0286(13) Uani 1 1 d . . . . .
H4A H 0.8561 0.8993 0.3153 0.034 Uiso 1 1 calc R U . . .
H4B H 0.9915 1.0001 0.3571 0.034 Uiso 1 1 calc R U . . .
N1 N 0.8607(12) 0.7932(5) 0.7090(4) 0.0543(16) Uani 1 1 d . . . . .
C7 C 0.8429(12) 0.7628(4) 0.6168(5) 0.0347(14) Uani 1 1 d . . . . .
C5 C 0.4566(13) 0.9466(6) 0.1418(5) 0.0460(17) Uani 1 1 d . . . . .
C6 C 0.5333(10) 0.7964(4) 0.4087(5) 0.0271(12) Uani 1 1 d . . . . .
H6A H 0.5221 0.7991 0.326 0.033 Uiso 1 1 calc R U . . .
H6B H 0.3883 0.76 0.4275 0.033 Uiso 1 1 calc R U . . .
N2 N 0.2958(13) 0.8904(5) 0.1174(6) 0.073(2) Uani 1 1 d . . . . .
C1 C 0.6291(9) 1.0787(4) 0.4620(4) 0.0246(12) Uani 1 1 d . . . . .
H1 H 0.7163 1.1327 0.4357 0.03 Uiso 1 1 calc R U . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se01 C7 1.840(6) . ?
Se01 C6 1.978(5) . ?
Se02 C5 1.828(8) . ?
Se02 C4 1.966(5) . ?
C3 C2 1.390(7) . ?
C3 C1 1.403(7) 3_676 ?
C3 C6 1.498(7) . ?
C2 C1 1.382(7) . ?
C2 C4 1.502(6) . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
N1 C7 1.151(8) . ?
C5 N2 1.151(9) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C1 C3 1.403(7) 3_676 ?
C1 H1 0.93 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 Se01 C6 95.3(2) . . ?
C5 Se02 C4 95.3(3) . . ?
C2 C3 C1 118.1(5) . 3_676 ?
C2 C3 C6 124.3(5) . . ?
C1 C3 C6 117.6(5) 3_676 . ?
C1 C2 C3 118.9(5) . . ?
C1 C2 C4 118.9(5) . . ?
C3 C2 C4 122.3(5) . . ?
C2 C4 Se02 114.0(4) . . ?
C2 C4 H4A 108.7 . . ?
Se02 C4 H4A 108.7 . . ?
C2 C4 H4B 108.7 . . ?
Se02 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
N1 C7 Se01 176.1(6) . . ?
N2 C5 Se02 179.5(7) . . ?
C3 C6 Se01 114.8(4) . . ?
C3 C6 H6A 108.6 . . ?
Se01 C6 H6A 108.6 . . ?
C3 C6 H6B 108.6 . . ?
Se01 C6 H6B 108.6 . . ?
H6A C6 H6B 107.5 . . ?
C2 C1 C3 123.1(5) . 3_676 ?
C2 C1 H1 118.5 . . ?
C3 C1 H1 118.5 3_676 . ?

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
C1 C3 C2 C1 -0.8(8) 3_676 . . . ?
C6 C3 C2 C1 178.4(5) . . . . ?
C1 C3 C2 C4 178.6(5) 3_676 . . . ?
C6 C3 C2 C4 -2.1(8) . . . . ?
C1 C2 C4 Se02 -69.8(6) . . . . ?
C3 C2 C4 Se02 110.7(5) . . . . ?
C2 C3 C6 Se01 77.5(6) . . . . ?
C1 C3 C6 Se01 -103.2(5) 3_676 . . . ?
C3 C2 C1 C3 0.9(9) . . . 3_676 ?
C4 C2 C1 C3 -178.6(5) . . . 3_676 ?

####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1820891'
_audit_update_record             
;
2018-01-31 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;

_audit_creation_date             2017-11-16T14:39:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_sum            'C15 H15 N3 Se3'
_chemical_formula_moiety         'C15 H15 N3 Se3'
_chemical_formula_weight         474.18

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

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

_cell_length_a                   18.8209(9)
_cell_length_b                   10.1135(5)
_cell_length_c                   17.9834(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.039(2)
_cell_angle_gamma                90
_cell_volume                     3380.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3250
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      24.78
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.863
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1824

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

_exptl_absorpt_coefficient_mu    6.525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.243
_exptl_absorpt_correction_T_max  0.593

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.4636  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------# 
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      -0.045065
_diffrn_orient_matrix_ub_12      -0.046963
_diffrn_orient_matrix_ub_13      -0.022412
_diffrn_orient_matrix_ub_21      0.01381
_diffrn_orient_matrix_ub_22      -0.07695
_diffrn_orient_matrix_ub_23      0.03414
_diffrn_orient_matrix_ub_31      -0.025941
_diffrn_orient_matrix_ub_32      0.04062
_diffrn_orient_matrix_ub_33      0.038763
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_number            15377
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.119
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_coverage         0
_reflns_number_total             3860
_reflns_number_gt                2312
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0349P)²+18.3108P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3860
_refine_ls_number_parameters     209
_refine_ls_number_restraints     3
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0991
_refine_ls_wR_factor_gt          0.0754
_refine_ls_goodness_of_fit_ref   0.891
_refine_ls_restrained_S_all      0.891
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.095

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


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

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1419(2) 0.2945(4) 0.4755(2) 0.0357(10) Uani 1 1 d . . . . .
C2 C 0.1411(2) 0.4330(4) 0.4786(2) 0.0370(10) Uani 1 1 d . . . . .
C3 C 0.1060(2) 0.4971(4) 0.5319(2) 0.0348(9) Uani 1 1 d . . . . .
C4 C 0.0714(2) 0.4222(4) 0.5818(2) 0.0356(10) Uani 1 1 d . . . . .
C5 C 0.0709(2) 0.2841(4) 0.5766(2) 0.0344(10) Uani 1 1 d . . . . .
C6 C 0.1067(2) 0.2186(4) 0.5237(2) 0.0364(10) Uani 1 1 d . . . . .
C7 C 0.1773(3) 0.5130(5) 0.4234(3) 0.0540(13) Uani 1 1 d . . . . .
H7A H 0.2016 0.4543 0.3938 0.081 Uiso 1 1 calc R U . . .
H7B H 0.2116 0.5727 0.4507 0.081 Uiso 1 1 calc R U . . .
H7C H 0.1416 0.5626 0.3908 0.081 Uiso 1 1 calc R U . . .
C8 C 0.0353(3) 0.4914(5) 0.6405(3) 0.0496(12) Uani 1 1 d . . . . .
H8A H -0.0106 0.5251 0.6173 0.074 Uiso 1 1 calc R U . . .
H8B H 0.065 0.5632 0.662 0.074 Uiso 1 1 calc R U . . .
H8C H 0.0285 0.4298 0.6793 0.074 Uiso 1 1 calc R U . . .
C9 C 0.1070(3) 0.0703(5) 0.5216(3) 0.0544(13) Uani 1 1 d . . . . .
H9A H 0.1247 0.0409 0.4772 0.082 Uiso 1 1 calc R U . . .
H9B H 0.0589 0.038 0.5209 0.082 Uiso 1 1 calc R U . . .
H9C H 0.1375 0.0371 0.5654 0.082 Uiso 1 1 calc R U . . .
C10 C 0.1817(2) 0.2249(5) 0.4201(2) 0.0438(11) Uani 1 1 d . . . . .
H10A H 0.1939 0.1365 0.4387 0.053 Uiso 1 1 calc R U . . .
H10B H 0.2263 0.2717 0.4181 0.053 Uiso 1 1 calc R U . . .
C11 C 0.0392(3) 0.1698(5) 0.3419(2) 0.0431(11) Uani 1 1 d . . . . .
C12 C 0.1029(3) 0.6457(5) 0.5347(2) 0.0441(11) Uani 1 1 d . . . . .
H12A H 0.0537 0.6718 0.5373 0.053 Uiso 1 1 calc R U . . .
H12B H 0.115 0.6803 0.488 0.053 Uiso 1 1 calc R U . . .
C13 C 0.2528(3) 0.6610(5) 0.6005(3) 0.0466(12) Uani 1 1 d . . . . .
N1 N -0.0168(2) 0.1457(5) 0.3550(2) 0.0617(12) Uani 1 1 d . . . . .
N2 N 0.3086(3) 0.6256(5) 0.5921(3) 0.0728(14) Uani 1 1 d . . . . .
Se1 Se 0.12715(3) 0.21157(6) 0.31607(3) 0.05613(18) Uani 1 1 d . . . . .
Se2 Se 0.16681(3) 0.73003(5) 0.61964(3) 0.04755(16) Uani 1 1 d . . . . .
C141 C 0.0317(3) 0.2043(5) 0.6275(3) 0.0477(12) Uani 0.293(8) 1 d D . P A 1
H14A H 0.0215 0.1184 0.6042 0.057 Uiso 0.293(8) 1 calc R U P A 1
H14B H -0.0143 0.2469 0.6288 0.057 Uiso 0.293(8) 1 calc R U P A 1
C151 C 0.1686(8) 0.178(3) 0.7131(16) 0.073(4) Uani 0.293(8) 1 d D . P A 1
N31 N 0.2264(8) 0.197(3) 0.7047(14) 0.136(5) Uani 0.293(8) 1 d D . P A 1
Se31 Se 0.07774(19) 0.1739(6) 0.73336(18) 0.0525(10) Uani 0.293(8) 1 d D . P A
1
C142 C 0.0317(3) 0.2043(5) 0.6275(3) 0.0477(12) Uani 0.707(8) 1 d D . P A 2
H14C H 0.0065 0.1322 0.599 0.057 Uiso 0.707(8) 1 calc R U P A 2
H14D H -0.004 0.2597 0.6457 0.057 Uiso 0.707(8) 1 calc R U P A 2
C152 C 0.1660(4) 0.2592(11) 0.7252(6) 0.073(4) Uani 0.707(8) 1 d D . P A 2
N32 N 0.2124(5) 0.3334(14) 0.7308(6) 0.136(5) Uani 0.707(8) 1 d D . P A 2
Se32 Se 0.09844(18) 0.1298(3) 0.71574(15) 0.0741(8) Uani 0.707(8) 1 d D . P A 2



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.401(6) . ?
C1 C2 1.401(6) . ?
C1 C10 1.510(6) . ?
C2 C3 1.406(6) . ?
C2 C7 1.523(6) . ?
C3 C4 1.409(6) . ?
C3 C12 1.505(6) . ?
C4 C5 1.399(6) . ?
C4 C8 1.515(6) . ?
C5 C6 1.415(6) . ?
C5 C142 1.498(6) . ?
C5 C141 1.498(6) . ?
C6 C9 1.500(7) . ?
C7 H7A 0.96 . ?
C7 H7B 0.96 . ?
C7 H7C 0.96 . ?
C8 H8A 0.96 . ?
C8 H8B 0.96 . ?
C8 H8C 0.96 . ?
C9 H9A 0.96 . ?
C9 H9B 0.96 . ?
C9 H9C 0.96 . ?
C10 Se1 1.993(4) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 N1 1.141(5) . ?
C11 Se1 1.837(5) . ?
C12 Se2 1.982(4) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C13 N2 1.142(6) . ?
C13 Se2 1.843(5) . ?
C141 Se31 1.988(5) . ?
C141 H14A 0.97 . ?
C141 H14B 0.97 . ?
C151 N31 1.137(13) . ?
C151 Se31 1.804(11) . ?
C142 Se32 2.010(5) . ?
C142 H14C 0.97 . ?
C142 H14D 0.97 . ?
C152 N32 1.144(10) . ?
C152 Se32 1.813(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.9(4) . . ?
C6 C1 C10 119.0(4) . . ?
C2 C1 C10 120.1(4) . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 C7 120.4(4) . . ?
C1 C2 C7 119.7(4) . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 C12 120.6(4) . . ?
C4 C3 C12 119.4(4) . . ?
C5 C4 C3 119.6(4) . . ?
C5 C4 C8 120.5(4) . . ?
C3 C4 C8 119.9(4) . . ?
C4 C5 C6 120.8(4) . . ?
C4 C5 C142 119.8(4) . . ?
C6 C5 C142 119.4(4) . . ?
C4 C5 C141 119.8(4) . . ?
C6 C5 C141 119.4(4) . . ?
C1 C6 C5 118.8(4) . . ?
C1 C6 C9 121.9(4) . . ?
C5 C6 C9 119.3(4) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 C10 Se1 114.5(3) . . ?
C1 C10 H10A 108.6 . . ?
Se1 C10 H10A 108.6 . . ?
C1 C10 H10B 108.6 . . ?
Se1 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
N1 C11 Se1 177.1(4) . . ?
C3 C12 Se2 115.7(3) . . ?
C3 C12 H12A 108.4 . . ?
Se2 C12 H12A 108.4 . . ?
C3 C12 H12B 108.4 . . ?
Se2 C12 H12B 108.4 . . ?
H12A C12 H12B 107.4 . . ?
N2 C13 Se2 174.8(5) . . ?
C11 Se1 C10 97.47(19) . . ?
C13 Se2 C12 97.9(2) . . ?
C5 C141 Se31 119.1(3) . . ?
C5 C141 H14A 107.6 . . ?
Se31 C141 H14A 107.6 . . ?
C5 C141 H14B 107.6 . . ?
Se31 C141 H14B 107.6 . . ?
H14A C141 H14B 107 . . ?
N31 C151 Se31 171(3) . . ?
C151 Se31 C141 95.0(9) . . ?
C5 C142 Se32 112.2(3) . . ?
C5 C142 H14C 109.2 . . ?
Se32 C142 H14C 109.2 . . ?
C5 C142 H14D 109.2 . . ?
Se32 C142 H14D 109.2 . . ?
H14C C142 H14D 107.9 . . ?
N32 C152 Se32 174.7(12) . . ?
C152 Se32 C142 98.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.5(6) . . . . ?
C10 C1 C2 C3 -177.9(4) . . . . ?
C6 C1 C2 C7 -177.6(4) . . . . ?
C10 C1 C2 C7 3.0(6) . . . . ?
C1 C2 C3 C4 -0.3(6) . . . . ?
C7 C2 C3 C4 178.7(4) . . . . ?
C1 C2 C3 C12 -178.4(4) . . . . ?
C7 C2 C3 C12 0.7(6) . . . . ?
C2 C3 C4 C5 -1.5(6) . . . . ?
C12 C3 C4 C5 176.6(4) . . . . ?
C2 C3 C4 C8 178.4(4) . . . . ?
C12 C3 C4 C8 -3.5(6) . . . . ?
C3 C4 C5 C6 2.2(6) . . . . ?
C8 C4 C5 C6 -177.7(4) . . . . ?
C3 C4 C5 C142 -177.6(4) . . . . ?
C8 C4 C5 C142 2.5(6) . . . . ?
C3 C4 C5 C141 -177.6(4) . . . . ?
C8 C4 C5 C141 2.5(6) . . . . ?
C2 C1 C6 C5 -0.8(6) . . . . ?
C10 C1 C6 C5 178.6(4) . . . . ?
C2 C1 C6 C9 -179.8(4) . . . . ?
C10 C1 C6 C9 -0.4(6) . . . . ?
C4 C5 C6 C1 -1.1(6) . . . . ?
C142 C5 C6 C1 178.7(4) . . . . ?
C141 C5 C6 C1 178.7(4) . . . . ?
C4 C5 C6 C9 178.0(4) . . . . ?
C142 C5 C6 C9 -2.2(6) . . . . ?
C141 C5 C6 C9 -2.2(6) . . . . ?
C6 C1 C10 Se1 98.6(4) . . . . ?
C2 C1 C10 Se1 -82.0(5) . . . . ?
C2 C3 C12 Se2 -105.7(4) . . . . ?
C4 C3 C12 Se2 76.2(5) . . . . ?
C4 C5 C141 Se31 -78.7(5) . . . . ?
C6 C5 C141 Se31 101.4(5) . . . . ?
C4 C5 C142 Se32 -99.8(4) . . . . ?
C6 C5 C142 Se32 80.4(4) . . . . ?

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

data_1b-DMF
_database_code_depnum_ccdc_archive 'CCDC 1820889'
_audit_update_record             
;
2018-01-31 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;

_audit_creation_date             2018-01-29T10:40:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_sum            'C18 H22 N4 O Se3'
_chemical_formula_moiety         'C15 H15 N3 Se3, C3 H7 N O'
_chemical_formula_weight         547.27

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

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

_cell_length_a                   5.9559(5)
_cell_length_b                   10.0181(8)
_cell_length_c                   17.6631(13)
_cell_angle_alpha                79.153(3)
_cell_angle_beta                 82.977(3)
_cell_angle_gamma                84.524(3)
_cell_volume                     1024.47(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9180
_cell_measurement_theta_min      3.46
_cell_measurement_theta_max      27.49
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536

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

_exptl_absorpt_coefficient_mu    5.4
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.495
_exptl_absorpt_correction_T_max  0.994

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.5351  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------#



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

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      0.091414
_diffrn_orient_matrix_ub_12      0.079651
_diffrn_orient_matrix_ub_13      -0.002319
_diffrn_orient_matrix_ub_21      0.142212
_diffrn_orient_matrix_ub_22      -0.057573
_diffrn_orient_matrix_ub_23      -0.011482
_diffrn_orient_matrix_ub_31      -0.01401
_diffrn_orient_matrix_ub_32      0.026982
_diffrn_orient_matrix_ub_33      -0.056781
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_number            31696
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.076
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_reflns_Friedel_coverage         0
_reflns_number_total             4678
_reflns_number_gt                4335
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0170P)²+2.3570P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4678
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0706
_refine_ls_wR_factor_gt          0.0694
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_restrained_S_all      1.198
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.865
_refine_diff_density_min         -1.3
_refine_diff_density_rms         0.103

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


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8205(5) 0.3951(3) 0.20752(16) 0.0134(5) Uani 1 1 d . . . . .
C2 C 0.9061(4) 0.2911(3) 0.26497(16) 0.0099(5) Uani 1 1 d . . . . .
C3 C 0.7876(5) 0.2700(3) 0.33975(16) 0.0097(5) Uani 1 1 d . . . . .
C4 C 0.5806(5) 0.3444(3) 0.35636(16) 0.0107(5) Uani 1 1 d . . . . .
C5 C 0.4902(5) 0.4412(3) 0.29632(17) 0.0122(5) Uani 1 1 d . . . . .
C6 C 0.6146(5) 0.4703(3) 0.22283(17) 0.0145(6) Uani 1 1 d . . . . .
C7 C 0.9626(6) 0.4309(3) 0.13114(18) 0.0206(7) Uani 1 1 d . . . . .
H7A H 1.1225 0.43 0.1415 0.025 Uiso 1 1 calc R U . . .
H7B H 0.9148 0.5253 0.1075 0.025 Uiso 1 1 calc R U . . .
C8 C 1.1244(5) 0.2091(3) 0.24639(18) 0.0170(6) Uani 1 1 d . . . . .
H8A H 1.253 0.2596 0.2516 0.026 Uiso 1 1 calc R U . . .
H8B H 1.1331 0.1926 0.1931 0.026 Uiso 1 1 calc R U . . .
H8C H 1.1291 0.1218 0.2824 0.026 Uiso 1 1 calc R U . . .
C9 C 0.8937(5) 0.1732(3) 0.40390(17) 0.0131(5) Uani 1 1 d . . . . .
H9A H 0.8188 0.1931 0.4542 0.016 Uiso 1 1 calc R U . . .
H9B H 1.0554 0.1912 0.4009 0.016 Uiso 1 1 calc R U . . .
C10 C 0.4603(5) 0.3266(3) 0.43784(18) 0.0184(6) Uani 1 1 d . . . . .
H10A H 0.433 0.2304 0.4562 0.028 Uiso 1 1 calc R U . . .
H10B H 0.315 0.3816 0.4378 0.028 Uiso 1 1 calc R U . . .
H10C H 0.5549 0.3564 0.4723 0.028 Uiso 1 1 calc R U . . .
C11 C 0.2653(5) 0.5171(3) 0.31231(19) 0.0168(6) Uani 1 1 d . . . . .
H11A H 0.1674 0.4562 0.3503 0.02 Uiso 1 1 calc R U . . .
H11B H 0.1917 0.5405 0.2637 0.02 Uiso 1 1 calc R U . . .
C12 C 0.5317(6) 0.5859(3) 0.16195(19) 0.0249(7) Uani 1 1 d . . . . .
H12A H 0.6189 0.6651 0.1594 0.037 Uiso 1 1 calc R U . . .
H12B H 0.3706 0.6104 0.1757 0.037 Uiso 1 1 calc R U . . .
H12C H 0.5519 0.557 0.1114 0.037 Uiso 1 1 calc R U . . .
C13 C 0.6391(6) 0.3198(3) 0.05555(18) 0.0216(7) Uani 1 1 d . . . . .
C14 C 0.5640(5) -0.0156(3) 0.40364(16) 0.0100(5) Uani 1 1 d . . . . .
C15 C 0.5954(5) 0.6773(3) 0.35234(19) 0.0178(6) Uani 1 1 d . . . . .
C16 C 0.9750(7) -0.1395(5) 0.1523(3) 0.0431(10) Uani 1 1 d . . . . .
H16 H 1.026 -0.143 0.2016 0.052 Uiso 1 1 calc R U . . .
C17 C 0.6364(8) -0.0102(4) 0.1984(2) 0.0388(10) Uani 1 1 d . . . . .
H17A H 0.4912 -0.0521 0.211 0.058 Uiso 1 1 calc R U . . .
H17B H 0.609 0.0875 0.1788 0.058 Uiso 1 1 calc R U . . .
H17C H 0.7151 -0.0233 0.2451 0.058 Uiso 1 1 calc R U . . .
C18 C 0.6867(7) -0.0626(4) 0.0657(2) 0.0342(9) Uani 1 1 d . . . . .
H18A H 0.6697 0.0336 0.0411 0.051 Uiso 1 1 calc R U . . .
H18B H 0.5387 -0.1011 0.0738 0.051 Uiso 1 1 calc R U . . .
H18C H 0.7921 -0.1127 0.0321 0.051 Uiso 1 1 calc R U . . .
N1 N 0.4460(6) 0.3189(4) 0.05520(19) 0.0347(7) Uani 1 1 d . . . . .
N2 N 0.3719(4) -0.0192(3) 0.40373(16) 0.0192(5) Uani 1 1 d . . . . .
N3 N 0.7876(5) 0.6757(3) 0.3535(2) 0.0301(7) Uani 1 1 d . . . . .
N4 N 0.7750(5) -0.0734(3) 0.13983(16) 0.0238(6) Uani 1 1 d . . . . .
O1 O 1.0999(6) -0.1968(4) 0.1052(3) 0.0715(12) Uani 1 1 d . . . . .
Se1 Se 0.95090(6) 0.31123(3) 0.05387(2) 0.02018(8) Uani 1 1 d . . . . .
Se2 Se 0.87562(5) -0.02419(3) 0.40260(2) 0.01180(7) Uani 1 1 d . . . . .
Se3 Se 0.28394(5) 0.68867(3) 0.35357(2) 0.01526(8) Uani 1 1 d . . . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.401(4) . ?
C1 C2 1.415(4) . ?
C1 C7 1.504(4) . ?
C2 C3 1.408(4) . ?
C2 C8 1.505(4) . ?
C3 C4 1.407(4) . ?
C3 C9 1.506(4) . ?
C4 C5 1.417(4) . ?
C4 C10 1.514(4) . ?
C5 C6 1.408(4) . ?
C5 C11 1.499(4) . ?
C6 C12 1.514(4) . ?
C7 Se1 1.990(3) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 Se2 1.995(3) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 Se3 2.006(3) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 N1 1.152(5) . ?
C13 Se1 1.848(4) . ?
C14 N2 1.148(4) . ?
C14 Se2 1.848(3) . ?
C15 N3 1.146(4) . ?
C15 Se3 1.845(3) . ?
C16 O1 1.234(6) . ?
C16 N4 1.328(5) . ?
C16 H16 0.95 . ?
C17 N4 1.446(5) . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 N4 1.452(4) . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 121.0(3) . . ?
C6 C1 C7 120.1(3) . . ?
C2 C1 C7 118.7(3) . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 C8 121.3(2) . . ?
C1 C2 C8 120.0(2) . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 C9 119.8(2) . . ?
C2 C3 C9 118.9(2) . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 C10 120.8(2) . . ?
C5 C4 C10 120.0(2) . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 C11 119.9(3) . . ?
C4 C5 C11 119.7(3) . . ?
C1 C6 C5 119.5(3) . . ?
C1 C6 C12 120.2(3) . . ?
C5 C6 C12 120.3(3) . . ?
C1 C7 Se1 116.5(2) . . ?
C1 C7 H7A 108.2 . . ?
Se1 C7 H7A 108.2 . . ?
C1 C7 H7B 108.2 . . ?
Se1 C7 H7B 108.2 . . ?
H7A C7 H7B 107.3 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C9 Se2 115.22(19) . . ?
C3 C9 H9A 108.5 . . ?
Se2 C9 H9A 108.5 . . ?
C3 C9 H9B 108.5 . . ?
Se2 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 Se3 114.2(2) . . ?
C5 C11 H11A 108.7 . . ?
Se3 C11 H11A 108.7 . . ?
C5 C11 H11B 108.7 . . ?
Se3 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 Se1 176.5(3) . . ?
N2 C14 Se2 175.5(2) . . ?
N3 C15 Se3 176.6(3) . . ?
O1 C16 N4 125.4(4) . . ?
O1 C16 H16 117.3 . . ?
N4 C16 H16 117.3 . . ?
N4 C17 H17A 109.5 . . ?
N4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 N4 C17 122.2(3) . . ?
C16 N4 C18 120.5(3) . . ?
C17 N4 C18 117.3(3) . . ?
C13 Se1 C7 97.48(14) . . ?
C14 Se2 C9 95.86(12) . . ?
C15 Se3 C11 96.83(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -3.9(4) . . . . ?
C7 C1 C2 C3 171.7(3) . . . . ?
C6 C1 C2 C8 178.3(3) . . . . ?
C7 C1 C2 C8 -6.1(4) . . . . ?
C1 C2 C3 C4 3.9(4) . . . . ?
C8 C2 C3 C4 -178.3(3) . . . . ?
C1 C2 C3 C9 -171.7(2) . . . . ?
C8 C2 C3 C9 6.0(4) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C9 C3 C4 C5 176.1(2) . . . . ?
C2 C3 C4 C10 -176.7(3) . . . . ?
C9 C3 C4 C10 -1.1(4) . . . . ?
C3 C4 C5 C6 -5.1(4) . . . . ?
C10 C4 C5 C6 172.2(3) . . . . ?
C3 C4 C5 C11 177.5(2) . . . . ?
C10 C4 C5 C11 -5.2(4) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
C7 C1 C6 C5 -176.1(3) . . . . ?
C2 C1 C6 C12 176.9(3) . . . . ?
C7 C1 C6 C12 1.4(4) . . . . ?
C4 C5 C6 C1 5.1(4) . . . . ?
C11 C5 C6 C1 -177.5(3) . . . . ?
C4 C5 C6 C12 -172.4(3) . . . . ?
C11 C5 C6 C12 5.1(4) . . . . ?
C6 C1 C7 Se1 -102.8(3) . . . . ?
C2 C1 C7 Se1 81.5(3) . . . . ?
C4 C3 C9 Se2 106.9(3) . . . . ?
C2 C3 C9 Se2 -77.4(3) . . . . ?
C6 C5 C11 Se3 -89.8(3) . . . . ?
C4 C5 C11 Se3 87.7(3) . . . . ?
O1 C16 N4 C17 179.1(5) . . . . ?
O1 C16 N4 C18 -0.6(7) . . . . ?

####################################################################### 
# 
# 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-DMF2
_database_code_depnum_ccdc_archive 'CCDC 1820893'
_audit_update_record             
;
2018-01-31 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;

_audit_creation_date             2018-01-18T14:29:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_sum            'C20 H24 N6 O2 Se4'
_chemical_formula_moiety         'C14 H10 N4 Se4, 2(C3 H7 N O)'

_chemical_formula_weight         696.29

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

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

_cell_length_a                   9.224(5)
_cell_length_b                   9.382(5)
_cell_length_c                   9.591(5)
_cell_angle_alpha                108.086(15)
_cell_angle_beta                 116.283(14)
_cell_angle_gamma                102.687(15)
_cell_volume                     642.3(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4824
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      27.42
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    1.8
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             338

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

_exptl_absorpt_coefficient_mu    5.74
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.184
_exptl_absorpt_correction_T_max  0.532

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.4572  0.7456                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------#


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

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      -0.127599
_diffrn_orient_matrix_ub_12      -0.021674
_diffrn_orient_matrix_ub_13      -0.046229
_diffrn_orient_matrix_ub_21      -0.037968
_diffrn_orient_matrix_ub_22      -0.103695
_diffrn_orient_matrix_ub_23      -0.103763
_diffrn_orient_matrix_ub_31      -0.002946
_diffrn_orient_matrix_ub_32      -0.063468
_diffrn_orient_matrix_ub_33      0.066119
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_number            14597
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.515
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_coverage         0
_reflns_number_total             2942
_reflns_number_gt                2248
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0299P)²+0.8650P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2942
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.04
_refine_ls_wR_factor_ref         0.0905
_refine_ls_wR_factor_gt          0.0808
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.891
_refine_diff_density_min         -0.94
_refine_diff_density_rms         0.108

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


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4060(5) 0.0004(4) 0.8377(4) 0.0257(7) Uani 1 1 d . . . . .
C2 C 0.5924(5) 0.0729(4) 0.9381(5) 0.0245(7) Uani 1 1 d . . . . .
C3 C 0.6806(5) 0.0703(4) 1.0975(5) 0.0269(8) Uani 1 1 d . . . . .
H3 H 0.8045 0.1186 1.1645 0.032 Uiso 1 1 calc R U . . .
C4 C 0.2964(5) -0.0054(5) 0.6642(5) 0.0315(8) Uani 1 1 d . . . . .
H4A H 0.1837 -0.1018 0.594 0.038 Uiso 1 1 calc R U . . .
H4B H 0.3572 -0.0189 0.6037 0.038 Uiso 1 1 calc R U . . .
C5 C 0.7000(5) 0.1479(5) 0.8791(5) 0.0330(9) Uani 1 1 d . . . . .
H5A H 0.6379 0.0842 0.7526 0.04 Uiso 1 1 calc R U . . .
H5B H 0.813 0.1397 0.9318 0.04 Uiso 1 1 calc R U . . .
C6 C 0.1140(6) 0.1623(5) 0.7724(5) 0.0384(9) Uani 1 1 d . . . . .
C7 C 0.9003(6) 0.4655(6) 1.1771(7) 0.0507(12) Uani 1 1 d . . . . .
C8 C 0.4529(6) -0.2824(5) 0.5139(6) 0.0412(10) Uani 1 1 d . . . . .
H8 H 0.3318 -0.3174 0.4686 0.049 Uiso 1 1 calc R U . . .
C9 C 0.4712(8) -0.3758(6) 0.7264(7) 0.0577(13) Uani 1 1 d . . . . .
H9A H 0.5285 -0.2994 0.848 0.087 Uiso 1 1 calc R U . . .
H9B H 0.486 -0.4758 0.7171 0.087 Uiso 1 1 calc R U . . .
H9C H 0.3465 -0.4003 0.6648 0.087 Uiso 1 1 calc R U . . .
C10 C 0.7387(7) -0.2522(7) 0.7264(7) 0.0634(14) Uani 1 1 d . . . . .
H10A H 0.764 -0.3478 0.7043 0.095 Uiso 1 1 calc R U . . .
H10B H 0.8021 -0.1833 0.8508 0.095 Uiso 1 1 calc R U . . .
H10C H 0.7756 -0.1915 0.675 0.095 Uiso 1 1 calc R U . . .
N1 N 0.0331(6) 0.1479(6) 0.8307(6) 0.0645(12) Uani 1 1 d . . . . .
N2 N 0.9947(7) 0.5246(7) 1.3253(7) 0.0848(16) Uani 1 1 d . . . . .
N3 N 0.5505(5) -0.3032(4) 0.6499(4) 0.0403(8) Uani 1 1 d . . . . .
O1 O 0.5093(4) -0.2206(4) 0.4430(4) 0.0547(8) Uani 1 1 d . . . . .
Se1 Se 0.24801(5) 0.19258(5) 0.67846(5) 0.03601(13) Uani 1 1 d . . . . .
Se2 Se 0.74703(6) 0.38161(5) 0.93915(6) 0.04390(15) Uani 1 1 d . . . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.388(5) 2_657 ?
C1 C2 1.399(5) . ?
C1 C4 1.491(5) . ?
C2 C3 1.389(5) . ?
C2 C5 1.497(5) . ?
C3 C1 1.388(5) 2_657 ?
C3 H3 0.93 . ?
C4 Se1 1.982(4) . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C5 Se2 1.976(4) . ?
C5 H5A 0.97 . ?
C5 H5B 0.97 . ?
C6 N1 1.123(5) . ?
C6 Se1 1.847(4) . ?
C7 N2 1.135(6) . ?
C7 Se2 1.835(5) . ?
C8 O1 1.223(5) . ?
C8 N3 1.320(5) . ?
C8 H8 0.93 . ?
C9 N3 1.451(5) . ?
C9 H9A 0.96 . ?
C9 H9B 0.96 . ?
C9 H9C 0.96 . ?
C10 N3 1.439(6) . ?
C10 H10A 0.96 . ?
C10 H10B 0.96 . ?
C10 H10C 0.96 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C1 C2 118.3(3) 2_657 . ?
C3 C1 C4 118.5(3) 2_657 . ?
C2 C1 C4 123.1(3) . . ?
C3 C2 C1 118.1(3) . . ?
C3 C2 C5 118.8(3) . . ?
C1 C2 C5 123.1(3) . . ?
C1 C3 C2 123.6(3) 2_657 . ?
C1 C3 H3 118.2 2_657 . ?
C2 C3 H3 118.2 . . ?
C1 C4 Se1 114.5(3) . . ?
C1 C4 H4A 108.6 . . ?
Se1 C4 H4A 108.6 . . ?
C1 C4 H4B 108.6 . . ?
Se1 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C2 C5 Se2 114.3(3) . . ?
C2 C5 H5A 108.7 . . ?
Se2 C5 H5A 108.7 . . ?
C2 C5 H5B 108.7 . . ?
Se2 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
N1 C6 Se1 178.2(4) . . ?
N2 C7 Se2 176.6(5) . . ?
O1 C8 N3 125.1(4) . . ?
O1 C8 H8 117.4 . . ?
N3 C8 H8 117.4 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 N3 C10 120.4(4) . . ?
C8 N3 C9 120.9(4) . . ?
C10 N3 C9 118.7(4) . . ?
C6 Se1 C4 95.76(17) . . ?
C7 Se2 C5 96.39(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 C2 C3 -0.1(6) 2_657 . . . ?
C4 C1 C2 C3 -179.7(3) . . . . ?
C3 C1 C2 C5 178.0(3) 2_657 . . . ?
C4 C1 C2 C5 -1.5(5) . . . . ?
C1 C2 C3 C1 0.1(6) . . . 2_657 ?
C5 C2 C3 C1 -178.1(3) . . . 2_657 ?
C3 C1 C4 Se1 93.8(4) 2_657 . . . ?
C2 C1 C4 Se1 -86.7(4) . . . . ?
C3 C2 C5 Se2 -95.3(4) . . . . ?
C1 C2 C5 Se2 86.6(4) . . . . ?
O1 C8 N3 C10 -0.2(7) . . . . ?
O1 C8 N3 C9 179.1(4) . . . . ?

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

data_1b-AcOEt
_database_code_depnum_ccdc_archive 'CCDC 1820890'
_audit_update_record             
;
2018-01-31 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;

_audit_creation_date             2017-12-12T15:50:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_sum            'C19 H23 N3 O2 Se3'
_chemical_formula_moiety         'C15 H15 N3 Se3, C4 H8 O2'
_chemical_formula_weight         562.28

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

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

_cell_length_a                   18.5055(17)
_cell_length_b                   10.3314(9)
_cell_length_c                   23.327(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.551(4)
_cell_angle_gamma                90
_cell_volume                     4252.2(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9707
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.5
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2208

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

_exptl_absorpt_coefficient_mu    5.209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.575
_exptl_absorpt_correction_T_max  0.901

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.4102  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------#


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

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      0.048038
_diffrn_orient_matrix_ub_12      -0.041607
_diffrn_orient_matrix_ub_13      0.024832
_diffrn_orient_matrix_ub_21      0.01331
_diffrn_orient_matrix_ub_22      -0.02149
_diffrn_orient_matrix_ub_23      -0.037384
_diffrn_orient_matrix_ub_31      0.026971
_diffrn_orient_matrix_ub_32      0.08471
_diffrn_orient_matrix_ub_33      0.002713
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_number            48703
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.139
_diffrn_reflns_theta_max         27.553
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_coverage         0
_reflns_number_total             4906
_reflns_number_gt                3914
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0263P)²+19.0169P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4906
_refine_ls_number_parameters     305
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0816
_refine_ls_wR_factor_gt          0.0741
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_restrained_S_all      1.06
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.535
_refine_diff_density_min         -1.471
_refine_diff_density_rms         0.107

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


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.13826(15) 0.2506(3) 0.47256(13) 0.0170(5) Uani 1 1 d . . . . .
C2 C 0.16914(15) 0.1831(3) 0.43306(12) 0.0172(6) Uani 1 1 d . . . . .
C3 C 0.17105(15) 0.0469(3) 0.43460(12) 0.0165(5) Uani 1 1 d . . . . .
C4 C 0.14270(15) -0.0221(3) 0.47490(12) 0.0162(5) Uani 1 1 d . . . . .
C5 C 0.11244(14) 0.0473(3) 0.51466(12) 0.0150(5) Uani 1 1 d . . . . .
C6 C 0.10952(15) 0.1838(3) 0.51312(12) 0.0167(5) Uani 1 1 d . . . . .
C7 C 0.14008(17) 0.3966(3) 0.47306(14) 0.0224(6) Uani 1 1 d . . . . .
H7A H 0.1907 0.4252 0.4719 0.027 Uiso 1 1 calc R U . . .
H7B H 0.1338 0.4272 0.5115 0.027 Uiso 1 1 calc R U . . .
C8 C 0.20024(17) 0.2573(3) 0.38971(14) 0.0231(6) Uani 1 1 d . . . . .
H8A H 0.1617 0.3176 0.3663 0.035 Uiso 1 1 calc R U . . .
H8B H 0.2138 0.1964 0.3624 0.035 Uiso 1 1 calc R U . . .
H8C H 0.2454 0.3058 0.4123 0.035 Uiso 1 1 calc R U . . .
C9 C 0.20513(16) -0.0258(3) 0.39316(13) 0.0220(6) Uani 1 1 d . . . . .
H9A H 0.2174 -0.1149 0.4087 0.026 Uiso 1 1 calc R U . . .
H9B H 0.2532 0.0167 0.3934 0.026 Uiso 1 1 calc R U . . .
C10 C 0.14350(18) -0.1680(3) 0.47508(15) 0.0250(6) Uani 1 1 d . . . . .
H10A H 0.1279 -0.1999 0.4336 0.037 Uiso 1 1 calc R U . . .
H10B H 0.1083 -0.2002 0.4959 0.037 Uiso 1 1 calc R U . . .
H10C H 0.1948 -0.1989 0.4959 0.037 Uiso 1 1 calc R U . . .
C11 C 0.08363(15) -0.0243(3) 0.55939(12) 0.0172(6) Uani 1 1 d . . . . .
H11A H 0.0755 -0.1161 0.5469 0.021 Uiso 1 1 calc R U . . .
H11B H 0.0339 0.0123 0.5586 0.021 Uiso 1 1 calc R U . . .
C12 C 0.07796(19) 0.2576(3) 0.55622(15) 0.0252(7) Uani 1 1 d . . . . .
H12A H 0.1196 0.2984 0.5873 0.038 Uiso 1 1 calc R U . . .
H12B H 0.0509 0.1977 0.5751 0.038 Uiso 1 1 calc R U . . .
H12C H 0.0429 0.3244 0.5342 0.038 Uiso 1 1 calc R U . . .
C13 C -0.0230(2) 0.4130(3) 0.42149(16) 0.0322(8) Uani 1 1 d . . . . .
C14 C 0.04805(17) -0.0532(3) 0.32734(13) 0.0232(6) Uani 1 1 d . . . . .
C15 C 0.23792(16) -0.0751(3) 0.62498(14) 0.0214(6) Uani 1 1 d . . . . .
N1 N -0.07768(18) 0.3762(3) 0.42901(16) 0.0417(8) Uani 1 1 d . . . . .
N2 N -0.00883(15) -0.0642(3) 0.33660(13) 0.0333(7) Uani 1 1 d . . . . .
N3 N 0.29242(16) -0.1081(3) 0.61569(14) 0.0325(7) Uani 1 1 d . . . . .
Se1 Se 0.06174(2) 0.48103(3) 0.40578(2) 0.02923(10) Uani 1 1 d . . . . .
Se2 Se 0.13729(2) -0.03512(4) 0.30851(2) 0.03591(11) Uani 1 1 d . . . . .
Se3 Se 0.15303(2) -0.01669(3) 0.64336(2) 0.01839(8) Uani 1 1 d . . . . .
O11 O 0.7783(3) 0.5551(5) 0.2898(2) 0.0293(10) Uani 0.5 1 d . . P A -1
O21 O 0.8859(4) 0.5010(6) 0.2707(3) 0.0234(13) Uani 0.5 1 d . . P A -1
C161 C 0.8249(16) 0.479(2) 0.2785(11) 0.032(6) Uani 0.5 1 d . . P A -1
C171 C 0.8050(4) 0.3321(6) 0.2747(3) 0.0309(15) Uani 0.5 1 d . . P A -1
H17A H 0.8493 0.2818 0.2732 0.046 Uiso 0.5 1 calc R U P A -1
H17B H 0.7628 0.3154 0.2383 0.046 Uiso 0.5 1 calc R U P A -1
H17C H 0.7904 0.3067 0.3101 0.046 Uiso 0.5 1 calc R U P A -1
C191 C 0.9755(4) 0.6472(6) 0.2515(3) 0.0265(14) Uani 0.5 1 d . . P A -1
H19A H 1.0136 0.5861 0.2747 0.04 Uiso 0.5 1 calc R U P A -1
H19B H 0.9959 0.7354 0.258 0.04 Uiso 0.5 1 calc R U P A -1
H19C H 0.9624 0.6258 0.2086 0.04 Uiso 0.5 1 calc R U P A -1
C181 C 0.9065(4) 0.6388(6) 0.2714(3) 0.0247(13) Uani 0.5 1 d . . P A -1
H18A H 0.9168 0.6747 0.3124 0.03 Uiso 0.5 1 calc R U P A -1
H18B H 0.8645 0.6886 0.2438 0.03 Uiso 0.5 1 calc R U P A -1
O12 O 0.7821(3) 0.4424(9) 0.2879(3) 0.060(2) Uani 0.5 1 d . . P B -2
O22 O 0.8982(4) 0.4487(6) 0.2770(4) 0.0284(14) Uani 0.5 1 d . . P B -2
C162 C 0.8294(14) 0.497(3) 0.2835(12) 0.044(8) Uani 0.5 1 d . . P B -2
C172 C 0.8390(5) 0.6477(8) 0.2814(4) 0.045(2) Uani 0.5 1 d . . P B -2
H17D H 0.7981 0.6903 0.2927 0.067 Uiso 0.5 1 calc R U P B -2
H17E H 0.837 0.6738 0.2405 0.067 Uiso 0.5 1 calc R U P B -2
H17F H 0.888 0.6729 0.3095 0.067 Uiso 0.5 1 calc R U P B -2
C182 C 0.9006(4) 0.3086(6) 0.2774(3) 0.0342(16) Uani 0.5 1 d . . P B -2
H18C H 0.8553 0.273 0.2471 0.041 Uiso 0.5 1 calc R U P B -2
H18D H 0.9022 0.275 0.3175 0.041 Uiso 0.5 1 calc R U P B -2
C192 C 0.9711(4) 0.2713(7) 0.2625(4) 0.045(2) Uani 0.5 1 d . . P B -2
H19D H 0.968 0.3028 0.2222 0.067 Uiso 0.5 1 calc R U P B -2
H19E H 0.9762 0.1768 0.2636 0.067 Uiso 0.5 1 calc R U P B -2
H19F H 1.0153 0.3098 0.2919 0.067 Uiso 0.5 1 calc R U P B -2



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.399(4) . ?
C1 C2 1.407(4) . ?
C1 C7 1.509(4) . ?
C2 C3 1.408(4) . ?
C2 C8 1.514(4) . ?
C3 C4 1.402(4) . ?
C3 C9 1.505(4) . ?
C4 C5 1.415(4) . ?
C4 C10 1.508(4) . ?
C5 C6 1.411(4) . ?
C5 C11 1.502(4) . ?
C6 C12 1.512(4) . ?
C7 Se1 1.988(3) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 Se2 1.997(3) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 Se3 1.994(3) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 N1 1.142(4) . ?
C13 Se1 1.854(4) . ?
C14 N2 1.142(4) . ?
C14 Se2 1.842(3) . ?
C15 N3 1.146(4) . ?
C15 Se3 1.850(3) . ?
O11 C161 1.25(3) . ?
O21 C161 1.22(3) . ?
O21 C181 1.472(8) . ?
C161 C171 1.56(3) . ?
C171 H17A 0.98 . ?
C171 H17B 0.98 . ?
C171 H17C 0.98 . ?
C191 C181 1.486(8) . ?
C191 H19A 0.98 . ?
C191 H19B 0.98 . ?
C191 H19C 0.98 . ?
C181 H18A 0.99 . ?
C181 H18B 0.99 . ?
O12 C162 1.07(3) . ?
O22 C162 1.42(3) . ?
O22 C182 1.448(9) . ?
C162 C172 1.57(3) . ?
C172 H17D 0.98 . ?
C172 H17E 0.98 . ?
C172 H17F 0.98 . ?
C182 C192 1.499(11) . ?
C182 H18C 0.99 . ?
C182 H18D 0.99 . ?
C192 H19D 0.98 . ?
C192 H19E 0.98 . ?
C192 H19F 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.7(3) . . ?
C6 C1 C7 120.0(3) . . ?
C2 C1 C7 119.2(3) . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 C8 119.9(3) . . ?
C3 C2 C8 120.7(3) . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 C9 119.4(3) . . ?
C2 C3 C9 119.7(3) . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 C10 120.3(3) . . ?
C5 C4 C10 120.7(3) . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 C11 119.4(2) . . ?
C4 C5 C11 119.9(2) . . ?
C1 C6 C5 119.4(3) . . ?
C1 C6 C12 120.2(3) . . ?
C5 C6 C12 120.4(2) . . ?
C1 C7 Se1 115.0(2) . . ?
C1 C7 H7A 108.5 . . ?
Se1 C7 H7A 108.5 . . ?
C1 C7 H7B 108.5 . . ?
Se1 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C9 Se2 113.5(2) . . ?
C3 C9 H9A 108.9 . . ?
Se2 C9 H9A 108.9 . . ?
C3 C9 H9B 108.9 . . ?
Se2 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 Se3 113.85(18) . . ?
C5 C11 H11A 108.8 . . ?
Se3 C11 H11A 108.8 . . ?
C5 C11 H11B 108.8 . . ?
Se3 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 Se1 176.1(3) . . ?
N2 C14 Se2 177.2(3) . . ?
N3 C15 Se3 177.0(3) . . ?
C13 Se1 C7 97.86(14) . . ?
C14 Se2 C9 96.34(12) . . ?
C15 Se3 C11 95.73(12) . . ?
C161 O21 C181 115.2(12) . . ?
O21 C161 O11 130(2) . . ?
O21 C161 C171 112.6(19) . . ?
O11 C161 C171 117(2) . . ?
C161 C171 H17A 109.5 . . ?
C161 C171 H17B 109.5 . . ?
H17A C171 H17B 109.5 . . ?
C161 C171 H17C 109.5 . . ?
H17A C171 H17C 109.5 . . ?
H17B C171 H17C 109.5 . . ?
C181 C191 H19A 109.5 . . ?
C181 C191 H19B 109.5 . . ?
H19A C191 H19B 109.5 . . ?
C181 C191 H19C 109.5 . . ?
H19A C191 H19C 109.5 . . ?
H19B C191 H19C 109.5 . . ?
O21 C181 C191 107.3(5) . . ?
O21 C181 H18A 110.3 . . ?
C191 C181 H18A 110.3 . . ?
O21 C181 H18B 110.3 . . ?
C191 C181 H18B 110.3 . . ?
H18A C181 H18B 108.5 . . ?
C162 O22 C182 112.0(13) . . ?
O12 C162 O22 128(2) . . ?
O12 C162 C172 129(2) . . ?
O22 C162 C172 103.2(18) . . ?
C162 C172 H17D 109.5 . . ?
C162 C172 H17E 109.5 . . ?
H17D C172 H17E 109.5 . . ?
C162 C172 H17F 109.5 . . ?
H17D C172 H17F 109.5 . . ?
H17E C172 H17F 109.5 . . ?
O22 C182 C192 106.5(6) . . ?
O22 C182 H18C 110.4 . . ?
C192 C182 H18C 110.4 . . ?
O22 C182 H18D 110.4 . . ?
C192 C182 H18D 110.4 . . ?
H18C C182 H18D 108.6 . . ?
C182 C192 H19D 109.5 . . ?
C182 C192 H19E 109.5 . . ?
H19D C192 H19E 109.5 . . ?
C182 C192 H19F 109.5 . . ?
H19D C192 H19F 109.5 . . ?
H19E C192 H19F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.1(4) . . . . ?
C7 C1 C2 C3 176.8(2) . . . . ?
C6 C1 C2 C8 -179.7(3) . . . . ?
C7 C1 C2 C8 -2.9(4) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C8 C2 C3 C4 179.6(3) . . . . ?
C1 C2 C3 C9 -179.0(2) . . . . ?
C8 C2 C3 C9 0.6(4) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C9 C3 C4 C5 178.5(2) . . . . ?
C2 C3 C4 C10 178.6(3) . . . . ?
C9 C3 C4 C10 -2.4(4) . . . . ?
C3 C4 C5 C6 1.1(4) . . . . ?
C10 C4 C5 C6 -178.0(3) . . . . ?
C3 C4 C5 C11 -178.4(2) . . . . ?
C10 C4 C5 C11 2.5(4) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
C7 C1 C6 C5 -176.1(2) . . . . ?
C2 C1 C6 C12 178.7(3) . . . . ?
C7 C1 C6 C12 1.9(4) . . . . ?
C4 C5 C6 C1 -1.2(4) . . . . ?
C11 C5 C6 C1 178.3(2) . . . . ?
C4 C5 C6 C12 -179.3(3) . . . . ?
C11 C5 C6 C12 0.2(4) . . . . ?
C6 C1 C7 Se1 -105.0(3) . . . . ?
C2 C1 C7 Se1 78.1(3) . . . . ?
C4 C3 C9 Se2 103.9(3) . . . . ?
C2 C3 C9 Se2 -77.1(3) . . . . ?
C6 C5 C11 Se3 -75.1(3) . . . . ?
C4 C5 C11 Se3 104.4(3) . . . . ?
C181 O21 C161 O11 -4(3) . . . . ?
C181 O21 C161 C171 177.7(10) . . . . ?
C161 O21 C181 C191 -171.0(14) . . . . ?
C182 O22 C162 O12 -1(3) . . . . ?
C182 O22 C162 C172 -179.6(10) . . . . ?
C162 O22 C182 C192 173.1(13) . . . . ?

