#------------------------------------------------------------------------------
#$Date: 2021-10-03 22:48:40 +0300 (Sun, 03 Oct 2021) $
#$Revision: 269477 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/90/4519055.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4519055
loop_
_publ_author_name
'He, Xinxin'
'Wang, Xinyan'
'Tse, Ying-Lung Steve'
'Ke, Zhihai'
'Yeung, Ying-Yeung'
_publ_section_title
;
 Bis-selenonium Cations as Bidentate Chalcogen Bond Donors in Catalysis
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              12632
_journal_page_last               12642
_journal_paper_doi               10.1021/acscatal.1c03622
_journal_year                    2021
_chemical_formula_sum            'C28 H28 B2 F8 Se2'
_chemical_formula_weight         696.04
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90.131(9)
_cell_angle_beta                 108.339(7)
_cell_angle_gamma                103.651(8)
_cell_formula_units_Z            2
_cell_length_a                   9.699(2)
_cell_length_b                   12.175(3)
_cell_length_c                   14.816(4)
_cell_measurement_reflns_used    3676
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     1608.2(7)
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_collection       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            42416
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         2.275
_exptl_absorpt_coefficient_mu    2.361
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4618
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       block
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.703
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5652
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0579P)²+1.4318P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1107
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4957
_reflns_number_total             5652
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c03622_si_002.cif
_cod_data_source_block           hxsec40715
_cod_database_code               4519055
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.385
_shelx_estimated_absorpt_t_max   0.538
loop_
_space_group_symop_operation_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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 1.11034(3) 0.69542(2) 0.64710(2) 0.04050(12) Uani 1 1 d . . . . .
Se2 Se 0.41385(3) 0.57440(3) 0.28264(2) 0.04289(12) Uani 1 1 d . . . . .
F1 F 1.1064(3) 0.4734(2) 0.7251(2) 0.0957(9) Uani 1 1 d . . . . .
F2 F 0.8890(4) 0.3729(3) 0.6219(2) 0.1075(10) Uani 1 1 d . . . . .
F3 F 0.9251(3) 0.3779(3) 0.7798(2) 0.1166(12) Uani 1 1 d . . . . .
F4 F 1.0526(4) 0.2872(3) 0.7159(3) 0.1112(11) Uani 1 1 d . . . . .
F5 F 0.4894(9) 0.2440(8) 0.4469(4) 0.246(4) Uani 1 1 d . . . . .
F6 F 0.3111(6) 0.1634(3) 0.3388(5) 0.196(3) Uani 1 1 d . . . . .
F7 F 0.5239(4) 0.2417(3) 0.3086(2) 0.1014(9) Uani 1 1 d . . . . .
F8 F 0.3766(3) 0.3446(2) 0.3374(2) 0.0936(9) Uani 1 1 d . . . . .
C1 C 1.1452(3) 0.8478(3) 0.6082(2) 0.0458(7) Uani 1 1 d . . . . .
C2 C 1.2215(4) 0.8696(3) 0.5433(3) 0.0649(10) Uani 1 1 d . . . . .
H2A H 1.251588 0.812279 0.518817 0.078 Uiso 1 1 calc R U . . .
C3 C 1.2524(5) 0.9780(5) 0.5155(4) 0.0878(15) Uani 1 1 d . . . . .
H3A H 1.302765 0.994308 0.471210 0.105 Uiso 1 1 calc R U . . .
C4 C 1.2084(6) 1.0629(4) 0.5533(4) 0.0851(15) Uani 1 1 d . . . . .
H4A H 1.231091 1.136220 0.534899 0.102 Uiso 1 1 calc R U . . .
C5 C 1.1332(6) 1.0407(4) 0.6166(3) 0.0777(13) Uani 1 1 d . . . . .
H5A H 1.103942 1.098410 0.641146 0.093 Uiso 1 1 calc R U . . .
C6 C 1.0990(5) 0.9309(3) 0.6452(3) 0.0623(9) Uani 1 1 d . . . . .
H6A H 1.046406 0.914576 0.688289 0.075 Uiso 1 1 calc R U . . .
C7 C 1.1388(4) 0.7301(3) 0.7805(2) 0.0460(7) Uani 1 1 d . . . . .
C8 C 1.2852(4) 0.7668(3) 0.8388(3) 0.0593(9) Uani 1 1 d . . . . .
H8A H 1.363424 0.769535 0.814547 0.071 Uiso 1 1 calc R U . . .
C9 C 1.3148(5) 0.7990(4) 0.9321(3) 0.0741(12) Uani 1 1 d . . . . .
H9A H 1.413556 0.825423 0.971613 0.089 Uiso 1 1 calc R U . . .
C10 C 1.2001(6) 0.7928(4) 0.9684(3) 0.0826(13) Uani 1 1 d . . . . .
H10A H 1.221480 0.814525 1.032518 0.099 Uiso 1 1 calc R U . . .
C11 C 1.0512(5) 0.7541(4) 0.9100(3) 0.0783(12) Uani 1 1 d . . . . .
H11A H 0.973404 0.749762 0.934880 0.094 Uiso 1 1 calc R U . . .
C12 C 1.0205(4) 0.7223(4) 0.8146(3) 0.0643(10) Uani 1 1 d . . . . .
H12A H 0.922095 0.696078 0.774469 0.077 Uiso 1 1 calc R U . . .
C13 C 0.8913(3) 0.6496(3) 0.5940(2) 0.0461(7) Uani 1 1 d . . . . .
H13A H 0.852860 0.584608 0.624601 0.055 Uiso 1 1 calc R U . . .
H13B H 0.849843 0.711157 0.605937 0.055 Uiso 1 1 calc R U . . .
C14 C 0.8440(3) 0.6195(3) 0.4872(2) 0.0467(7) Uani 1 1 d . . . . .
H14A H 0.874419 0.551876 0.475415 0.056 Uiso 1 1 calc R U . . .
H14B H 0.892761 0.680949 0.457606 0.056 Uiso 1 1 calc R U . . .
C15 C 0.6736(3) 0.5986(3) 0.4439(2) 0.0480(7) Uani 1 1 d . . . . .
H15A H 0.625395 0.538671 0.475121 0.058 Uiso 1 1 calc R U . . .
H15B H 0.643980 0.666897 0.454685 0.058 Uiso 1 1 calc R U . . .
C16 C 0.6224(3) 0.5652(3) 0.3377(2) 0.0484(7) Uani 1 1 d . . . . .
H16A H 0.629769 0.488533 0.326692 0.058 Uiso 1 1 calc R U . . .
H16B H 0.685396 0.615957 0.308003 0.058 Uiso 1 1 calc R U . . .
C17 C 0.4480(4) 0.7330(3) 0.2613(2) 0.0494(7) Uani 1 1 d . . . . .
C18 C 0.5243(5) 0.7793(3) 0.2000(3) 0.0625(9) Uani 1 1 d . . . . .
H18A H 0.563548 0.734753 0.168482 0.075 Uiso 1 1 calc R U . . .
C19 C 0.5405(6) 0.8938(4) 0.1867(3) 0.0812(14) Uani 1 1 d . . . . .
H19A H 0.591601 0.926326 0.145886 0.097 Uiso 1 1 calc R U . . .
C20 C 0.4835(6) 0.9587(4) 0.2319(4) 0.0836(14) Uani 1 1 d . . . . .
H20A H 0.494276 1.035075 0.221410 0.100 Uiso 1 1 calc R U . . .
C21 C 0.4104(6) 0.9131(4) 0.2928(4) 0.0919(16) Uani 1 1 d . . . . .
H21A H 0.372816 0.959032 0.324223 0.110 Uiso 1 1 calc R U . . .
C22 C 0.3906(5) 0.7980(3) 0.3089(3) 0.0689(10) Uani 1 1 d . . . . .
H22A H 0.340398 0.766673 0.350509 0.083 Uiso 1 1 calc R U . . .
C23 C 0.3604(4) 0.5081(3) 0.1530(2) 0.0475(7) Uani 1 1 d . . . . .
C24 C 0.2463(4) 0.5370(4) 0.0853(3) 0.0670(10) Uani 1 1 d . . . . .
H24A H 0.199879 0.589644 0.100589 0.080 Uiso 1 1 calc R U . . .
C25 C 0.2004(5) 0.4875(4) -0.0064(3) 0.0755(12) Uani 1 1 d . . . . .
H25A H 0.123073 0.507529 -0.053424 0.091 Uiso 1 1 calc R U . . .
C26 C 0.2672(6) 0.4094(4) -0.0289(3) 0.0874(15) Uani 1 1 d . . . . .
H26A H 0.235968 0.376556 -0.090994 0.105 Uiso 1 1 calc R U . . .
C27 C 0.3790(8) 0.3800(6) 0.0397(4) 0.134(3) Uani 1 1 d . U . . .
H27A H 0.424648 0.326645 0.024735 0.161 Uiso 1 1 calc R U . . .
C28 C 0.4264(7) 0.4300(5) 0.1337(3) 0.115(2) Uani 1 1 d . . . . .
H28A H 0.502138 0.409258 0.181391 0.138 Uiso 1 1 calc R U . . .
B1 B 0.9922(5) 0.3762(4) 0.7120(3) 0.0580(10) Uani 1 1 d . . . . .
B2 B 0.4243(6) 0.2487(4) 0.3525(4) 0.0688(13) 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
_geom_angle_publ_flag
C1 Se1 C7 99.00(14) . . ?
C1 Se1 C13 99.49(14) . . ?
C7 Se1 C13 101.21(14) . . ?
C17 Se2 C23 100.29(14) . . ?
C17 Se2 C16 99.23(15) . . ?
C23 Se2 C16 102.07(14) . . ?
C6 C1 C2 121.9(3) . . ?
C6 C1 Se1 121.4(3) . . ?
C2 C1 Se1 116.7(3) . . ?
C3 C2 C1 118.6(4) . . ?
C2 C3 C4 120.1(5) . . ?
C5 C4 C3 120.9(4) . . ?
C4 C5 C6 120.1(5) . . ?
C1 C6 C5 118.4(4) . . ?
C8 C7 C12 121.8(3) . . ?
C8 C7 Se1 115.7(3) . . ?
C12 C7 Se1 122.5(3) . . ?
C9 C8 C7 119.4(4) . . ?
C8 C9 C10 120.4(4) . . ?
C9 C10 C11 120.5(4) . . ?
C12 C11 C10 119.3(4) . . ?
C7 C12 C11 118.6(4) . . ?
C14 C13 Se1 109.8(2) . . ?
C13 C14 C15 109.6(3) . . ?
C16 C15 C14 110.8(3) . . ?
C15 C16 Se2 108.3(2) . . ?
C22 C17 C18 121.5(4) . . ?
C22 C17 Se2 116.5(3) . . ?
C18 C17 Se2 122.0(3) . . ?
C17 C18 C19 118.3(4) . . ?
C20 C19 C18 121.1(5) . . ?
C19 C20 C21 120.3(4) . . ?
C20 C21 C22 121.1(5) . . ?
C17 C22 C21 117.7(4) . . ?
C28 C23 C24 121.7(3) . . ?
C28 C23 Se2 120.7(3) . . ?
C24 C23 Se2 117.5(3) . . ?
C23 C24 C25 119.2(4) . . ?
C26 C25 C24 120.6(4) . . ?
C27 C26 C25 119.6(4) . . ?
C26 C27 C28 120.2(5) . . ?
C23 C28 C27 118.8(4) . . ?
F4 B1 F3 112.1(4) . . ?
F4 B1 F1 107.5(4) . . ?
F3 B1 F1 109.9(4) . . ?
F4 B1 F2 109.1(4) . . ?
F3 B1 F2 110.1(4) . . ?
F1 B1 F2 108.1(4) . . ?
F6 B2 F7 117.4(5) . . ?
F6 B2 F8 109.5(5) . . ?
F7 B2 F8 112.8(4) . . ?
F6 B2 F5 98.4(6) . . ?
F7 B2 F5 108.2(5) . . ?
F8 B2 F5 109.5(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C1 1.929(3) . ?
Se1 C7 1.938(3) . ?
Se1 C13 1.957(3) . ?
Se2 C17 1.925(3) . ?
Se2 C23 1.943(3) . ?
Se2 C16 1.959(3) . ?
F1 B1 1.381(5) . ?
F2 B1 1.388(5) . ?
F3 B1 1.360(5) . ?
F4 B1 1.342(6) . ?
F5 B2 1.349(7) . ?
F6 B2 1.282(7) . ?
F7 B2 1.341(5) . ?
F8 B2 1.349(5) . ?
C1 C6 1.376(5) . ?
C1 C2 1.378(5) . ?
C2 C3 1.377(6) . ?
C3 C4 1.386(8) . ?
C4 C5 1.350(8) . ?
C5 C6 1.399(6) . ?
C7 C8 1.375(5) . ?
C7 C12 1.377(5) . ?
C8 C9 1.357(5) . ?
C9 C10 1.366(7) . ?
C10 C11 1.395(7) . ?
C11 C12 1.383(6) . ?
C13 C14 1.519(4) . ?
C14 C15 1.530(5) . ?
C15 C16 1.517(4) . ?
C17 C22 1.374(5) . ?
C17 C18 1.385(5) . ?
C18 C19 1.387(6) . ?
C19 C20 1.348(8) . ?
C20 C21 1.357(8) . ?
C21 C22 1.400(6) . ?
C23 C28 1.341(6) . ?
C23 C24 1.357(5) . ?
C24 C25 1.377(6) . ?
C25 C26 1.364(6) . ?
C26 C27 1.352(7) . ?
C27 C28 1.407(7) . ?
