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_7049676
_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         'C52 H68 Au Cl2 N6, F6 P, 2(C H2 Cl2)'
_chemical_formula_sum            'C54 H72 Au Cl6 F6 N6 P'
_chemical_formula_weight         1359.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-05-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2018-07-24 deposited with the CCDC.    2019-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.728(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.2352(7)
_cell_length_b                   10.8348(7)
_cell_length_c                   22.2774(16)
_cell_measurement_reflns_used    8302
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.393
_cell_measurement_theta_min      2.430
_cell_volume                     3191.0(4)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200.0
_diffrn_measured_fraction_theta_full 0.997
_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  0.0787
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20957
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.414
_diffrn_reflns_theta_min         2.430
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.637
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0767 before and 0.0519 after correction. The Ratio of minimum to maximum transmission is 0.7240. 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    1.415
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   0.7454
_exptl_transmission_factor_min   0.5397
_refine_diff_density_max         1.560
_refine_diff_density_min         -1.320
_refine_diff_density_rms         0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         6525
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0575
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0828P)^2^+10.2927P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1444
_refine_ls_wR_factor_ref         0.1603
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5200
_reflns_number_total             6525
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt01018a2.cif
_cod_data_source_block           mo_xxy2017112303au_0m_a
_cod_depositor_comments
'Adding full bibliography for 7049675--7049689.cif.'
_cod_database_code               7049676
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C24, C26, C25, P1, F1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C27) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(Cl3A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(F1) \\sim Ueq, Uanis(C26) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
Uanis(Cl3) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Others
 Sof(H27C)=Sof(H27D)=Sof(Cl3A)=1-FVAR(1)
 Sof(Cl3)=Sof(H27A)=Sof(H27B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C24(H24), C9(H9), C21(H21), C12(H12)
5.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C27(H27C,H27D)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C5(H5), C17(H17), C19(H19), C18(H18)
5.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C13(H13A,H13B,H13C), C10(H10A,H10B,H10C), C26(H26A,H26B,
 H26C), C23(H23A,H23B,H23C), C22(H22A,H22B,H22C), C11(H11A,H11B,H11C), C14(H14A,
 H14B,H14C)
;
_shelx_res_checksum              76249
_shelx_fab_checksum              14200
_olex2_submission_special_instructions 'No special instructions were received'