Halogen-bonding-induced diverse aggregation of 4,5-diiodo-1,2,3-triazolium salts with different anions
Xu, Xingyu; Huang, Shiqing; Zhang, Zengyu; Cao, Lei; Yan, Xiaoyu; Beilstein Journal of Organic Chemistry 16 (2020) 78–87; doi:10.3762/bjoc.16.10

data_4037814
_publ_section_title
;
 Halogen-bonding-induced diverse aggregation of
 4,5-diiodo-1,2,3-triazolium salts with different anions
;
_journal_name_full               'Beilstein Journal of Organic Chemistry'
_journal_page_first              78
_journal_page_last               87
_journal_paper_doi               10.3762/bjoc.16.10
_journal_volume                  16
_journal_year                    2020
_chemical_formula_moiety
'2(C20 H22 I2 N3), 4(C H2 Cl2), C10 H8 N2, 2(B F4)'
_chemical_formula_sum            'C54 H60 B2 Cl8 F8 I4 N8'
_chemical_formula_weight         1785.92
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.369(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.1509(13)
_cell_length_b                   18.7643(13)
_cell_length_c                   20.4941(16)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.451
_cell_measurement_theta_min      2.266
_cell_volume                     6974.1(9)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      149.97
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            67328
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_min         2.244
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.156
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0849 before and 0.0567 after correction. The Ratio of minimum to maximum transmission is 0.7555. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_description       block
_exptl_crystal_F_000             3480
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_refine_diff_density_max         3.009
_refine_diff_density_min         -2.192
_refine_diff_density_rms         0.201
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     809
_refine_ls_number_reflns         15951
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0965
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0179P)^2^+172.3415P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2020
_refine_ls_wR_factor_ref         0.2088
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13187
_reflns_number_total             15951
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            mo_XXY1891_0m_a.cif
_cod_data_source_block           mo_xxy1891_0m_a
_cod_depositor_comments
'Adding full bibliography for 4037807--4037815.cif.'
_cod_database_code               4037814
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.555
_shelx_estimated_absorpt_t_min   0.465
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C16) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C41) \\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F1)
\\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(C53) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(Cl4) \\sim Ueq, Uanis(Cl2) \\sim Ueq, Uanis(F1) \\sim Ueq: with sigma of
0.001 and sigma for terminal atoms of 0.002
3. Others
 Sof(I3A)=1-FVAR(1)
 Sof(I3)=FVAR(1)
 Sof(I4A)=1-FVAR(2)
 Sof(I4)=FVAR(2)
 Sof(I2A)=1-FVAR(3)
 Sof(I2)=FVAR(3)
 Sof(I1A)=1-FVAR(4)
 Sof(I1)=FVAR(4)
4.a Secondary CH2 refined with riding coordinates:
 C56(H56A,H56B), C54(H54A,H54B), C55(H55A,H55B), C53(H53A,H53B)
4.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C31(H31), C27(H27), C26(H26), C5(H5), C25(H25), C45(H45), C39(H39),
 C29(H29), C7(H7), C37(H37), C43(H43), C32(H32), C30(H30), C13(H13), C11(H11)
4.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C48(H48A,H48B,
 H48C), C49(H49A,H49B,H49C), C47(H47A,H47B,H47C), C15(H15A,H15B,H15C), C50(H50A,
 H50B,H50C), C52(H52A,H52B,H52C), C51(H51A,H51B,H51C), C19(H19A,H19B,H19C),
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              18727
_shelx_hkl_checksum              52621
_shelx_fab_checksum              32364
_olex2_submission_special_instructions 'No special instructions were received'