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_7049687
_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         'C28 H34 Cl I Ir N3 O2, C H2 Cl2'
_chemical_formula_sum            'C29 H36 Cl3 I Ir N3 O2'
_chemical_formula_weight         884.06
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/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                 100.473(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7391(7)
_cell_length_b                   20.1341(15)
_cell_length_c                   15.7287(10)
_cell_measurement_reflns_used    9848
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      30.550
_cell_measurement_theta_min      2.357
_cell_volume                     3344.2(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      200.01
_diffrn_measured_fraction_theta_full 0.998
_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  0.0389
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            43360
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.588
_diffrn_reflns_theta_min         2.357
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.184
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0843 before and 0.0504 after correction. The Ratio of minimum to maximum transmission is 0.5954. 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    1.756
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   0.7461
_exptl_transmission_factor_min   0.4442
_refine_diff_density_max         1.018
_refine_diff_density_min         -1.002
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         10222
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0185P)^2^+5.7894P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0613
_refine_ls_wR_factor_ref         0.0663
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8208
_reflns_number_total             10222
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt01018a2.cif
_cod_data_source_block           mo_xxy20180102ircl_0m_a
_cod_depositor_comments
'Adding full bibliography for 7049675--7049689.cif.'
_cod_database_code               7049687
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.455
_shelx_estimated_absorpt_t_min   0.409
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C24(H24), C21(H21), C18(H18), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C5(H5), C13(H13), C12(H12), C11(H11)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C17(H17A,H17B,H17C), C16(H16A,
 H16B,H16C)
;
_shelx_res_checksum              20877
_olex2_submission_special_instructions 'No special instructions were received'