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_4037813
_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, C2 F3 O2'
_chemical_formula_sum            'C22 H22 F3 I2 N3 O2'
_chemical_formula_weight         671.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 117.810(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.3708(19)
_cell_length_b                   11.2189(12)
_cell_length_c                   22.842(2)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.505
_cell_measurement_theta_min      2.518
_cell_volume                     5070.6(8)
_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      150.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0535
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            49462
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.536
_diffrn_reflns_theta_min         2.518
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.525
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0897 before and 0.0644 after correction. The Ratio of minimum to maximum transmission is 0.6984. 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    1.758
_exptl_crystal_description       block
_exptl_crystal_F_000             2592
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         3.580
_refine_diff_density_min         -1.871
_refine_diff_density_rms         0.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         11611
_refine_ls_number_restraints     630
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0914
_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^)+(0.0304P)^2^+228.9145P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2130
_refine_ls_wR_factor_ref         0.2216
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9297
_reflns_number_total             11611
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            mo_XXY4251_0m_a.cif
_cod_data_source_block           mo_xxy4251_0m_a
_cod_depositor_comments
'Adding full bibliography for 4037807--4037815.cif.'
_cod_original_cell_volume        5070.7(9)
_cod_database_code               4037813
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.703
_shelx_estimated_absorpt_t_min   0.594
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F11) \\sim Ueq, Uanis(F0AA) \\sim Ueq, Uanis(F13) \\sim Ueq, Uanis(F1AA)
\\sim Ueq, Uanis(F7) \\sim Ueq, Uanis(F2AA) \\sim Ueq: with sigma of 0.001 and
sigma for terminal atoms of 0.002
Uanis(C015) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(F14) \\sim Ueq, Uanis(F16) \\sim Ueq, Uanis(F15) \\sim Ueq: with sigma of
0.001 and sigma for terminal atoms of 0.002
Uanis(F0AA) \\sim Ueq, Uanis(F2AA) \\sim Ueq, Uanis(F1AA) \\sim Ueq,
Uanis(F15A) \\sim Ueq, Uanis(F16A) \\sim Ueq, Uanis(F14A) \\sim Ueq: with sigma
of 0.001 and sigma for terminal atoms of 0.002
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F0AA)=Sof(F2AA)=Sof(F1AA)=1-FVAR(1)
 Sof(F7)=Sof(F11)=Sof(F13)=FVAR(1)
 Sof(F15A)=Sof(F16A)=Sof(F14A)=1-FVAR(2)
 Sof(F16)=Sof(F15)=Sof(F14)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C7(H7), C19(H19), C21(H21), C27(H27), C25(H25), C34(H34), C36(H36)
5.b Fitted hexagon refined as free rotating group:
 C13(C11,C10,C8,C7,C6), C15(C16,C17,C19,C20,C21), C23(C28,C27,C26,C25,C24),
 C35(C34,C33,C32,C37,C36)
5.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C38(H38A,H38B,H38C), C14(H14A,H14B,H14C), C9(H9A,H9B,
 H9C), C12(H12A,H12B,H12C), C31(H31A,H31B,H31C), C30(H30A,H30B,H30C), C5(H5A,
 H5B,H5C), C22(H22A,H22B,H22C), C40(H40A,H40B,H40C), C39(H39A,H39B,H39C),
 C29(H29A,H29B,H29C)
;
_shelx_res_checksum              67130
_shelx_hkl_checksum              34901
_olex2_submission_special_instructions 'No special instructions were received'