Versatile halogenation <i>via</i> a C<sub>NHC</sub>^C<sub>sp3</sub> palladacycle intermediate.
Teng, Qiaoqiao; Liu, Ziwei; Song, Haobin; Liu, Jiayu; Zhao, Yaru; Jiang, Weihua; Huynh, Han Vinh; Meng, Qi; Dalton transactions (Cambridge, England : 2003) 52 (2023) 2223–2226; doi:10.1039/d3dt00113j

data_7712303
_publ_section_title
;
 Versatile halogenation <i>via</i> a C<sub>NHC</sub>^C<sub>sp3</sub>
 palladacycle intermediate.
;
_journal_issue                   8
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2223
_journal_page_last               2226
_journal_paper_doi               10.1039/d3dt00113j
_journal_volume                  52
_journal_year                    2023
_chemical_formula_moiety         'C23 H27 Br3 N4 Pd'
_chemical_formula_sum            'C23 H27 Br3 N4 Pd'
_chemical_formula_weight         705.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-12-14 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.572(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6138(6)
_cell_length_b                   13.7132(9)
_cell_length_c                   17.3306(11)
_cell_measurement_reflns_used    4064
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.37
_cell_volume                     2500.5(3)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.1003
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_number            5091
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.393
_diffrn_reflns_theta_min         1.936
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.554
_exptl_absorpt_correction_T_max  0.7895
_exptl_absorpt_correction_T_min  0.5632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 21831 reflections, Rint = 0.0684
 (9586 with I > 3sig(I), Rint = 0.0490)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.904
_refine_diff_density_min         -1.346
_refine_diff_density_rms         0.256
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         5091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1408
_refine_ls_R_factor_gt           0.0821
_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^)+(0.0071P)^2^+82.8651P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1548
_refine_ls_wR_factor_ref         0.1747
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3369
_reflns_number_total             5091
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt00113j2.cif
_cod_data_source_block           tqq_0m_4
_cod_depositor_comments
'Adding full bibliography for 7712302--7712304.cif.'
_cod_database_code               7712303
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.769
_shelx_estimated_absorpt_t_min   0.555
_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:
 C2(H2), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C8(H8), C15(H15), C14(H14), C7(H7), C19(H19), C23(H23),
 C20(H20), C22(H22), C21(H21)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C13(H13A,H13B,H13C), C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'