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_4037808
_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         'C20 H22 I2 N3, Br'
_chemical_formula_sum            'C20 H22 Br I2 N3'
_chemical_formula_weight         638.11
_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_Hall           'I -4'
_space_group_name_H-M_alt        'I -4'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-12-09
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.5982(13)
_cell_length_b                   23.5982(13)
_cell_length_c                   9.8455(6)
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      29.782
_cell_measurement_theta_min      2.241
_cell_volume                     5482.7(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_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  0.0536
_diffrn_reflns_av_unetI/netI     0.0824
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20093
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.104
_diffrn_reflns_theta_min         2.241
_exptl_absorpt_coefficient_mu    3.759
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.3914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1218 before and 0.0778 after correction. The Ratio of minimum to maximum transmission is 0.5245. 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    1.546
_exptl_crystal_description       block
_exptl_crystal_F_000             2432
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.29
_refine_diff_density_max         1.899
_refine_diff_density_min         -1.273
_refine_diff_density_rms         0.173
_refine_ls_abs_structure_details
;
 Flack x determined using 2391 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.057(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         8644
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0799P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1425
_refine_ls_wR_factor_ref         0.1553
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                6652
_reflns_number_total             8644
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            mo_xxy201809201_0m.cif
_cod_data_source_block           mo_xxy201809201_0m
_cod_depositor_comments
'Adding full bibliography for 4037807--4037815.cif.'
_cod_original_cell_volume        5482.7(7)
_cod_database_code               4037808
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.409
_shelx_estimated_absorpt_t_min   0.337
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.663(2)
 0.337(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C5(H5), C7(H7)
4.b Fitted hexagon refined as free rotating group:
 C14(C9,C10,C11,C12,C13), C5(C4,C3,C8,C7,C6)
4.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C15(H15A,H15B,H15C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C17(H17A,H17B,H17C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              62653
_shelx_hkl_checksum              15629
_olex2_submission_special_instructions 'No special instructions were received'