4-Halo-1,2,3-triazolylidenes: stable carbenes featuring halogen bonding.
Xu, Xingyu; Zhang, Zengyu; Huang, Shiqing; Cao, Lei; Liu, Wei; Yan, Xiaoyu; Dalton transactions (Cambridge, England : 2003) 48 (2019) 6931–6941; doi:10.1039/c9dt01018a

data_7049688
_publ_section_title
;
 4-Halo-1,2,3-triazolylidenes: stable carbenes featuring halogen bonding.
;
_journal_issue                   20
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6931
_journal_page_last               6941
_journal_paper_doi               10.1039/c9dt01018a
_journal_volume                  48
_journal_year                    2019
_chemical_formula_moiety         'C39 H52 Au I N5, B F4'
_chemical_formula_sum            'C39 H52 Au B F4 I N5'
_chemical_formula_weight         1001.53
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-09-20 deposited with the CCDC.    2019-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                70.161(3)
_cell_angle_beta                 87.658(3)
_cell_angle_gamma                83.006(3)
_cell_formula_units_Z            1
_cell_length_a                   9.2835(9)
_cell_length_b                   9.7312(10)
_cell_length_c                   12.3642(12)
_cell_measurement_reflns_used    9501
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      36.335
_cell_measurement_theta_min      2.240
_cell_volume                     1042.87(18)
_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      149.94
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0279
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14683
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.820
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.317
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.5876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0770 before and 0.0554 after correction. The Ratio of minimum to maximum transmission is 0.7865. 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    1.595
_exptl_crystal_description       block
_exptl_crystal_F_000             494
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.886
_refine_diff_density_min         -1.000
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.342(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         7394
_refine_ls_number_restraints     56
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0243
_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^)+(0.0341P)^2^+0.6290P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0638
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                7394
_reflns_number_total             7394
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt01018a2.cif
_cod_data_source_block           mo_xxy201808233_0m_b
_cod_depositor_comments
'Adding full bibliography for 7049675--7049689.cif.'
_cod_database_code               7049688
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.648
_shelx_estimated_absorpt_t_min   0.564
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.658(6)
 0.342(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Rigid bond restraints
 C22, C23, C24
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C27, C25
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C31, C33
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq, Uanis(F3) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(C23) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C25)
\\sim Ueq, Uanis(C26) \\sim Ueq: with sigma of 0.001 and sigma for terminal
atoms of 0.002
Uanis(C24) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5.a Ternary CH refined with riding coordinates:
 C37(H37), C27(H27), C28(H28), C22(H22), C31(H31), C34(H34)
5.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C12(H12), C14(H14), C6(H6), C20(H20), C18(H18), C8(H8), C7(H7),
 C5(H5), C13(H13)
5.c Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C36(H36A,H36B,H36C), C30(H30A,H30B,H30C), C23(H23A,H23B,
 H23C), C39(H39A,H39B,H39C), C26(H26A,H26B,H26C), C25(H25A,H25B,H25C), C33(H33A,
 H33B,H33C), C29(H29A,H29B,H29C), C24(H24A,H24B,H24C), C32(H32A,H32B,H32C),
 C35(H35A,H35B,H35C)
;
_shelx_res_checksum              86178
_olex2_submission_special_instructions 'No special instructions were received'