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_4037810
_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, Cl'
_chemical_formula_sum            'C20 H22 Cl I2 N3'
_chemical_formula_weight         593.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_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                 134.483(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   32.770(4)
_cell_length_b                   9.7269(13)
_cell_length_c                   23.215(3)
_cell_measurement_reflns_used    8136
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.309
_cell_measurement_theta_min      2.459
_cell_volume                     5279.4(12)
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_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  0.0557
_diffrn_reflns_av_unetI/netI     0.0904
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            20706
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.582
_diffrn_reflns_theta_min         2.268
_exptl_absorpt_coefficient_mu    2.491
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_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    1.494
_exptl_crystal_description       block
_exptl_crystal_F_000             2288
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.620
_refine_diff_density_min         -1.721
_refine_diff_density_rms         0.150
_refine_ls_abs_structure_details
;
 Flack x determined using 2292 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(19)
_refine_ls_extinction_coef       0.00014(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         9877
_refine_ls_number_restraints     301
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0591
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0301P)^2^+75.9162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1272
_reflns_Friedel_coverage         0.881
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                7569
_reflns_number_total             9877
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            mo_xxy318_0m.cif
_cod_data_source_block           mo_xxy318_0m_a_sq
_cod_depositor_comments
'Adding full bibliography for 4037807--4037815.cif.'
_cod_original_cell_volume        5279.3(12)
_cod_database_code               4037810
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.706
_shelx_estimated_absorpt_t_min   0.691
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7623(15)
 0.2377(15)
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
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
4.a Aromatic/amide H refined with riding coordinates:
 C34(H34), C36(H36), C18(H18), C16(H16), C9(H9), C7(H7), C24(H24), C30(H30)
4.b Fitted hexagon refined as free rotating group:
 C32(C33,C34,C35,C36,C37), C19(C18,C17,C16,C15,C14), C8(C9,C10,C5,C6,C7),
 C26(C24,C25,C30,C28,C27)
4.c Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C21(H21A,H21B,H21C), C12(H12A,H12B,H12C), C11(H11A,H11B,
 H11C), C29(H29A,H29B,H29C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C39(H39A,
 H39B,H39C), C38(H38A,H38B,H38C), C13(H13A,H13B,H13C), C31(H31A,H31B,H31C),
 C2AA(H2AA,H2AB,H2AC)
;
_shelx_res_checksum              42406
_shelx_hkl_checksum              15579
_shelx_fab_checksum              22083
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'