#------------------------------------------------------------------------------
#$Date: 2019-10-28 09:23:29 +0200 (Mon, 28 Oct 2019) $
#$Revision: 219800 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/83/2108354.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2108354
loop_
_publ_author_name
'Riel, Asia Marie S.'
'Jeannin, Olivier'
'Berryman, Orion B.'
'Fourmigué, Marc'
_publ_section_title
;
 Co-crystals of an organic triselenocyanate with ditopic Lewis bases:
 recurrent chalcogen bond interactions motifs
;
_journal_coeditor_code           AW5020SUP1
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              34
_journal_page_last               38
_journal_paper_doi               10.1107/S2052520618017778
_journal_volume                  75
_journal_year                    2019
_chemical_formula_moiety         '2(C15 H15 N3 Se3), C6 H4 O2'
_chemical_formula_sum            'C36 H34 N6 O2 Se6'
_chemical_formula_weight         1056.46
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2017-12-12T15:05:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                93.538(5)
_cell_angle_beta                 117.528(5)
_cell_angle_gamma                95.282(5)
_cell_formula_units_Z            1
_cell_length_a                   10.008(2)
_cell_length_b                   10.4345(19)
_cell_length_c                   10.760(2)
_cell_measurement_reflns_used    3951
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.64
_cell_measurement_theta_min      2.74
_cell_measurement_wavelength     0.71073
_cell_volume                     985.3(3)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_UB_11      0.018177
_diffrn_orient_matrix_UB_12      -0.029041
_diffrn_orient_matrix_UB_13      -0.080572
_diffrn_orient_matrix_UB_21      -0.109758
_diffrn_orient_matrix_UB_22      0.001444
_diffrn_orient_matrix_UB_23      -0.067245
_diffrn_orient_matrix_UB_31      0.023667
_diffrn_orient_matrix_UB_32      0.092458
_diffrn_orient_matrix_UB_33      -0.011195
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0878
_diffrn_reflns_av_unetI/netI     0.1003
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24136
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         3.073
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.61
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.817
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1368
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0523P)²+1.8613P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.114
_refine_ls_wR_factor_ref         0.1404
_reflns_Friedel_coverage         0
_reflns_number_gt                2412
_reflns_number_total             4486
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            aw5020sup1.cif
_cod_data_source_block           1BQ
_cod_depositor_comments
;
Adding full bibliography for 2108353--2108355.cif.

2019-10-27
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C18 H17 N3 O Se3'
_cod_original_formula_weight         528.23
_cod_original_formula_moiety         'C15 H15 N3 Se3, 0.5(C6 H4 O2)'
_cod_original_formula_units_Z            2
_cod_database_code               2108354
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.2459(7) -0.1361(5) 0.1014(6) 0.0321(14) Uani 1 1 d . .
C2 C 0.3681(6) -0.0463(5) 0.1990(6) 0.0340(14) Uani 1 1 d . .
C3 C 0.3457(7) 0.0362(5) 0.2937(6) 0.0338(14) Uani 1 1 d . .
C4 C 0.2058(7) 0.0294(5) 0.2918(6) 0.0348(14) Uani 1 1 d . .
C5 C 0.0830(6) -0.0576(5) 0.1908(6) 0.0349(14) Uani 1 1 d . .
C6 C 0.1044(6) -0.1417(5) 0.0958(6) 0.0351(14) Uani 1 1 d . .
C7 C 0.2677(7) -0.2239(6) -0.0014(7) 0.0436(16) Uani 1 1 d . .
H7A H 0.3608 -0.19 -0.0024 0.052 Uiso 1 1 calc R U
H7B H 0.1842 -0.2221 -0.095 0.052 Uiso 1 1 calc R U
C8 C 0.5219(7) -0.0412(7) 0.2045(7) 0.0507(17) Uani 1 1 d . .
H8A H 0.5181 -0.0053 0.1231 0.076 Uiso 1 1 calc R U
H8B H 0.5488 -0.1272 0.2054 0.076 Uiso 1 1 calc R U
H8C H 0.5966 0.0121 0.2885 0.076 Uiso 1 1 calc R U
C9 C 0.4780(7) 0.1338(5) 0.4028(7) 0.0404(15) Uani 1 1 d . .
H9A H 0.5726 0.1083 0.4118 0.048 Uiso 1 1 calc R U
H9B H 0.4802 0.1311 0.4937 0.048 Uiso 1 1 calc R U
C10 C 0.1824(8) 0.1204(6) 0.3930(7) 0.0491(17) Uani 1 1 d . .
H10A H 0.2792 0.1548 0.4713 0.074 Uiso 1 1 calc R U
H10B H 0.1208 0.0739 0.4268 0.074 Uiso 1 1 calc R U
H10C H 0.1324 0.1902 0.3452 0.074 Uiso 1 1 calc R U
C11 C -0.0713(7) -0.0630(6) 0.1813(7) 0.0437(16) Uani 1 1 d . .
H11A H -0.1461 -0.0676 0.0827 0.052 Uiso 1 1 calc R U
H11B H -0.0758 0.017 0.2292 0.052 Uiso 1 1 calc R U
C12 C -0.0276(7) -0.2393(6) -0.0105(7) 0.0502(18) Uani 1 1 d . .
H12A H -0.0014 -0.277 -0.0785 0.075 Uiso 1 1 calc R U
H12B H -0.1157 -0.1964 -0.0577 0.075 Uiso 1 1 calc R U
H12C H -0.0494 -0.3061 0.0375 0.075 Uiso 1 1 calc R U
C13 C 0.4240(9) -0.3722(7) 0.2222(9) 0.066(2) Uani 1 1 d . .
C14 C 0.4365(8) 0.2799(6) 0.1744(9) 0.0514(18) Uani 1 1 d . .
C15 C 0.0408(8) -0.1809(7) 0.4401(9) 0.0529(19) Uani 1 1 d . .
C16 C -0.0120(9) -0.5398(7) 0.3680(8) 0.060(2) Uani 1 1 d . .
C17 C 0.1339(9) -0.5270(7) 0.4971(9) 0.067(2) Uani 1 1 d . .
H17 H 0.2198 -0.5459 0.4908 0.08 Uiso 1 1 calc R U
C18 C 0.1471(8) -0.4896(6) 0.6225(8) 0.056(2) Uani 1 1 d . .
H18 H 0.2409 -0.482 0.7032 0.067 Uiso 1 1 calc R U
N1 N 0.5095(9) -0.3534(6) 0.3385(8) 0.091(3) Uani 1 1 d . .
N2 N 0.4193(7) 0.2576(7) 0.0607(8) 0.0695(18) Uani 1 1 d . .
N3 N 0.1399(8) -0.1689(6) 0.5479(8) 0.073(2) Uani 1 1 d . .
O1 O -0.0224(7) -0.5746(6) 0.2513(7) 0.0907(19) Uani 1 1 d . .
Se1 Se 0.27892(10) -0.40669(7) 0.03883(8) 0.0644(3) Uani 1 1 d . .
Se2 Se 0.46601(8) 0.31386(6) 0.35479(8) 0.0526(2) Uani 1 1 d . .
Se3 Se -0.12835(8) -0.21052(7) 0.26265(8) 0.0524(2) Uani 1 1 d . .
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_
_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
C6 C1 C2 120.8(5) . .
C6 C1 C7 119.9(5) . .
C2 C1 C7 119.3(5) . .
C1 C2 C3 118.7(5) . .
C1 C2 C8 120.4(5) . .
C3 C2 C8 120.9(5) . .
C4 C3 C2 121.1(5) . .
C4 C3 C9 119.2(5) . .
C2 C3 C9 119.7(5) . .
C3 C4 C5 119.8(5) . .
C3 C4 C10 120.6(5) . .
C5 C4 C10 119.5(5) . .
C4 C5 C6 119.6(5) . .
C4 C5 C11 121.2(5) . .
C6 C5 C11 119.2(5) . .
C1 C6 C5 119.9(5) . .
C1 C6 C12 120.5(5) . .
C5 C6 C12 119.6(5) . .
C1 C7 Se1 114.8(4) . .
C1 C7 H7A 108.6 . .
Se1 C7 H7A 108.6 . .
C1 C7 H7B 108.6 . .
Se1 C7 H7B 108.6 . .
H7A C7 H7B 107.5 . .
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 113.6(4) . .
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 114.9(4) . .
C5 C11 H11A 108.5 . .
Se3 C11 H11A 108.5 . .
C5 C11 H11B 108.5 . .
Se3 C11 H11B 108.5 . .
H11A C11 H11B 107.5 . .
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 176.6(9) . .
N2 C14 Se2 179.2(7) . .
N3 C15 Se3 176.5(7) . .
O1 C16 C18 119.7(7) . 2_546
O1 C16 C17 121.1(8) . .
C18 C16 C17 119.2(7) 2_546 .
C18 C17 C16 121.9(8) . .
C18 C17 H17 119 . .
C16 C17 H17 119 . .
C17 C18 C16 118.9(7) . 2_546
C17 C18 H18 120.6 . .
C16 C18 H18 120.6 2_546 .
C13 Se1 C7 96.6(3) . .
C14 Se2 C9 97.2(3) . .
C15 Se3 C11 97.3(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.385(8) .
C1 C2 1.399(8) .
C1 C7 1.498(8) .
C2 C3 1.403(8) .
C2 C8 1.509(8) .
C3 C4 1.385(8) .
C3 C9 1.529(8) .
C4 C5 1.398(8) .
C4 C10 1.514(8) .
C5 C6 1.410(8) .
C5 C11 1.495(8) .
C6 C12 1.517(8) .
C7 Se1 1.983(6) .
C7 H7A 0.97 .
C7 H7B 0.97 .
C8 H8A 0.96 .
C8 H8B 0.96 .
C8 H8C 0.96 .
C9 Se2 1.978(6) .
C9 H9A 0.97 .
C9 H9B 0.97 .
C10 H10A 0.96 .
C10 H10B 0.96 .
C10 H10C 0.96 .
C11 Se3 1.982(6) .
C11 H11A 0.97 .
C11 H11B 0.97 .
C12 H12A 0.96 .
C12 H12B 0.96 .
C12 H12C 0.96 .
C13 N1 1.134(9) .
C13 Se1 1.816(8) .
C14 N2 1.159(9) .
C14 Se2 1.829(8) .
C15 N3 1.114(9) .
C15 Se3 1.857(9) .
C16 O1 1.240(9) .
C16 C18 1.460(11) 2_546
C16 C17 1.466(10) .
C17 C18 1.323(10) .
C17 H17 0.93 .
C18 C16 1.460(11) 2_546
C18 H18 0.93 .
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_4
C6 C1 C2 C3 1.5(8) . .
C7 C1 C2 C3 179.4(5) . .
C6 C1 C2 C8 179.8(5) . .
C7 C1 C2 C8 -2.3(8) . .
C1 C2 C3 C4 0.1(8) . .
C8 C2 C3 C4 -178.2(5) . .
C1 C2 C3 C9 179.1(5) . .
C8 C2 C3 C9 0.9(8) . .
C2 C3 C4 C5 -2.3(8) . .
C9 C3 C4 C5 178.7(5) . .
C2 C3 C4 C10 -179.0(5) . .
C9 C3 C4 C10 2.0(8) . .
C3 C4 C5 C6 2.8(8) . .
C10 C4 C5 C6 179.6(5) . .
C3 C4 C5 C11 -177.1(5) . .
C10 C4 C5 C11 -0.3(8) . .
C2 C1 C6 C5 -1.0(8) . .
C7 C1 C6 C5 -178.9(5) . .
C2 C1 C6 C12 179.9(5) . .
C7 C1 C6 C12 2.0(8) . .
C4 C5 C6 C1 -1.2(8) . .
C11 C5 C6 C1 178.7(5) . .
C4 C5 C6 C12 177.9(5) . .
C11 C5 C6 C12 -2.2(8) . .
C6 C1 C7 Se1 -75.7(6) . .
C2 C1 C7 Se1 106.4(5) . .
C4 C3 C9 Se2 -77.2(6) . .
C2 C3 C9 Se2 103.8(5) . .
C4 C5 C11 Se3 -102.8(6) . .
C6 C5 C11 Se3 77.3(6) . .
O1 C16 C17 C18 179.7(7) . .
C18 C16 C17 C18 -0.1(11) 2_546 .
C16 C17 C18 C16 0.1(11) . 2_546
