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_7712304
_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         'C27 H33 Br N4 O2 Pd'
_chemical_formula_sum            'C27 H33 Br N4 O2 Pd'
_chemical_formula_weight         631.88
_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             2020-07-21
_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                 96.1070(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.1679(6)
_cell_length_b                   9.3786(3)
_cell_length_c                   35.7626(15)
_cell_measurement_reflns_used    9223
_cell_measurement_temperature    160
_cell_measurement_theta_max      26.023
_cell_measurement_theta_min      2.291
_cell_volume                     5392.0(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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      160.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_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  0.0806
_diffrn_reflns_av_unetI/netI     0.0741
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            47847
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.402
_diffrn_reflns_theta_min         2.246
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.201
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1034 before and 0.0587 after correction. The Ratio of minimum to maximum transmission is 0.7518. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_description       block
_exptl_crystal_F_000             2560
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.925
_refine_diff_density_min         -1.039
_refine_diff_density_rms         0.135
_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     641
_refine_ls_number_reflns         10939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0344P)^2^+18.5821P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1157
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7603
_reflns_number_total             10939
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt00113j2.cif
_cod_data_source_block           2_0m
_cod_depositor_comments
'Adding full bibliography for 7712302--7712304.cif.'
_cod_database_code               7712304
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.879
_shelx_estimated_absorpt_t_min   0.734
_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:
 C25(H25), C52(H52), C1(H1), C39(H39), C43(H43), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C38(H38A,H38B), C24(H24A,H24B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C23(H23), C36(H36), C37(H37), C49(H49), C51(H51), C50(H50),
 C48(H48), C34(H34), C14(H14), C30(H30), C5(H5), C6(H6), C8(H8), C7(H7),
 C32(H32), C33(H33), C15(H15), C18(H18), C31(H31), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C53(H53A,H53B,H53C), C42(H42A,H42B,H42C), C54(H54A,H54B,
 H54C), C2(H2A,H2B,H2C), C41(H41A,H41B,H41C), C44(H44A,H44B,H44C), C27(H27A,
 H27B,H27C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'