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_7049680
_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         'C26 H35 Br N3, F6 P, C3 H6 O'
_chemical_formula_sum            'C29 H41 Br F6 N3 O P'
_chemical_formula_weight         672.53
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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   mixed
_audit_creation_date             2018-05-22
_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                66.594(3)
_cell_angle_beta                 89.451(3)
_cell_angle_gamma                66.597(3)
_cell_formula_units_Z            2
_cell_length_a                   11.8567(10)
_cell_length_b                   11.8619(9)
_cell_length_c                   14.1909(12)
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.503
_cell_measurement_theta_min      2.301
_cell_volume                     1654.7(2)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      199.99
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.0375
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23760
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_min         2.253
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.350
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1249 before and 0.0457 after correction. The Ratio of minimum to maximum transmission is 0.8102. 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    1.350
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.6041
_refine_diff_density_max         1.974
_refine_diff_density_min         -0.930
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         7587
_refine_ls_number_restraints     69
_refine_ls_restrained_S_all      1.217
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0614
_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^)+(0.0870P)^2^+2.7416P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1604
_refine_ls_wR_factor_ref         0.1715
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6189
_reflns_number_total             7587
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt01018a2.cif
_cod_data_source_block           mo_xxy20171211brt_0m
_cod_depositor_comments
'Adding full bibliography for 7049675--7049689.cif.'
_cod_database_code               7049680
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.823
_shelx_estimated_absorpt_t_min   0.747
_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. Rigid bond restraints
 F2, P1, F1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 P1, F4, F6, F2, F1, F3, F5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 P1, F1
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
3. Uiso/Uaniso restraints and constraints
Uanis(F2) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F3) \\sim
Ueq, Uanis(F1) \\sim Ueq, Uanis(F5) \\sim Ueq: with sigma of 0.001 and sigma
for terminal atoms of 0.002
Uanis(C29) \\sim Ueq, Uanis(C27) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
4. Others
 Sof(Br2)=1-FVAR(1)
 Sof(Br1)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C23(H23), C9(H9), C24(H24), C12(H12)
5.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C17(H17), C7(H7), C18(H18), C5(H5), C6(H6)
5.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C14(H14A,H14B,H14C), C22(H22A,H22B,
 H22C), C21(H21A,H21B,H21C), C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C11(H11A,
 H11B,H11C), C29(H29A,H29B,H29C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              23320
_olex2_submission_special_instructions 'No special instructions were received'