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_7049683
_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 Cl Cu I N3)'
_chemical_formula_sum            'C52 H68 Cl2 Cu2 I2 N6'
_chemical_formula_weight         1228.90
_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     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                101.894(4)
_cell_angle_beta                 98.660(4)
_cell_angle_gamma                108.263(4)
_cell_formula_units_Z            2
_cell_length_a                   12.4075(14)
_cell_length_b                   15.6524(19)
_cell_length_c                   15.669(2)
_cell_measurement_reflns_used    9554
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.396
_cell_measurement_theta_min      2.583
_cell_volume                     2750.9(6)
_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 0.995
_diffrn_measured_fraction_theta_max 0.990
_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  0.0963
_diffrn_reflns_av_unetI/netI     0.1226
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            41940
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.590
_diffrn_reflns_theta_min         2.222
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.031
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1199 before and 0.0721 after correction. The Ratio of minimum to maximum transmission is 0.7674. 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    1.484
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.5722
_refine_diff_density_max         1.999
_refine_diff_density_min         -1.137
_refine_diff_density_rms         0.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     593
_refine_ls_number_reflns         12622
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1621
_refine_ls_R_factor_gt           0.0782
_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^)+(0.1389P)^2^+1.6854P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2060
_refine_ls_wR_factor_ref         0.2516
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6787
_reflns_number_total             12622
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt01018a2.cif
_cod_data_source_block           mo_xxy2017112302_0m_a
_cod_depositor_comments
'Adding full bibliography for 7049675--7049689.cif.'
_cod_original_cell_volume        2750.8(6)
_cod_database_code               7049683
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.675
_shelx_estimated_absorpt_t_min   0.631
_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
 C0AA, C51, C50, C36, C35, C37
 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(C37) \\sim Ueq, Uanis(C51) \\sim Ueq, Uanis(C0AA) \\sim Ueq: with sigma
of 0.001 and sigma for terminal atoms of 0.002
4.a Ternary CH refined with riding coordinates:
 C23(H23), C27(H27), C38(H38), C41(H41), C50(H50), C35(H35), C44(H44), C47(H47)
4.b Aromatic/amide H refined with riding coordinates:
 C31(H31), C21(H21), C14(H14), C33(H33), C32(H32), C13(H13), C15(H15),
 C19(H19), C9(H9), C20(H20), C8(H8), C7(H7)
4.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C39(H39A,H39B,H39C), C26(H26A,H26B,H26C), C25(H25A,H25B,
 H25C), C40(H40A,H40B,H40C), C42(H42A,H42B,H42C), C48(H48A,H48B,H48C), C45(H45A,
 H45B,H45C), C49(H49A,H49B,H49C), C36(H36A,H36B,H36C), C43(H43A,H43B,H43C),
 C46(H46A,H46B,H46C), C28(H28A,H28B,H28C), C37(H37A,H37B,H37C), C51(H51A,H51B,
 H51C), C0AA(H0AA,H0AB,H0AC)
;
_shelx_res_checksum              4915
_olex2_submission_special_instructions 'No special instructions were received'