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_7049682
_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         '2(C26 H34 Br Cu I N3)'
_chemical_formula_sum            'C52 H68 Br2 Cu2 I2 N6'
_chemical_formula_weight         1317.82
_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   geom
_atom_sites_solution_primary     dual
_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                102.049(2)
_cell_angle_beta                 99.133(2)
_cell_angle_gamma                107.604(2)
_cell_formula_units_Z            2
_cell_length_a                   12.5144(10)
_cell_length_b                   15.6168(12)
_cell_length_c                   15.7106(12)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.797
_cell_measurement_theta_min      2.307
_cell_volume                     2779.9(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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      199.99
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0644
_diffrn_reflns_av_unetI/netI     0.0861
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            37050
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.224
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.351
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0859 before and 0.0563 after correction. The Ratio of minimum to maximum transmission is 0.7756. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.5783
_refine_diff_density_max         1.363
_refine_diff_density_min         -1.106
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     593
_refine_ls_number_reflns         12722
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0526
_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^)+(0.0346P)^2^+5.1741P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1134
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7844
_reflns_number_total             12722
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt01018a2.cif
_cod_data_source_block           mo_hsq20171115_0m
_cod_depositor_comments
'Adding full bibliography for 7049675--7049689.cif.'
_cod_database_code               7049682
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.616
_shelx_estimated_absorpt_t_min   0.540
_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
 C44, C45, C50, C51, C52
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C28, C26, C27
 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(C51) \\sim Ueq, Uanis(C52) \\sim Ueq, Uanis(C28) \\sim Ueq: with sigma of
0.001 and sigma for terminal atoms of 0.002
Uanis(C45) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4.a Ternary CH refined with riding coordinates:
 C20(H20), C17(H17), C47(H47), C23(H23), C41(H41), C50(H50), C44(H44), C26(H26)
4.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C33(H33), C8(H8), C7(H7), C15(H15), C31(H31), C13(H13), C39(H39),
 C32(H32), C14(H14), C38(H38), C37(H37)
4.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C25(H25A,H25B,H25C), C22(H22A,H22B,H22C), C19(H19A,H19B,
 H19C), C24(H24A,H24B,H24C), C42(H42A,H42B,H42C), C49(H49A,H49B,H49C), C48(H48A,
 H48B,H48C), C43(H43A,H43B,H43C), C18(H18A,H18B,H18C), C27(H27A,H27B,H27C),
 C46(H46A,H46B,H46C), C45(H45A,H45B,H45C), C51(H51A,H51B,H51C), C28(H28A,H28B,
 H28C), C52(H52A,H52B,H52C)
;
_shelx_res_checksum              55286
_olex2_submission_special_instructions 'No special instructions were received'