Pd-catalyzed Suzuki-type cross-coupling of 2-pyridyl carbamoyl fluorides.
Jabbarpoor, Maryam; LeBlanc, Jesse; Chen, Zichuan; Cadwallader, Dusty; Le, Christine M.; Chemical communications (Cambridge, England) 60 (2024) 8700–8703; doi:10.1039/d4cc02431a

data_7133373
_publ_section_title
;
 Pd-catalyzed Suzuki-type cross-coupling of 2-pyridyl carbamoyl fluorides.
;
_journal_issue                   66
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8700
_journal_page_last               8703
_journal_paper_doi               10.1039/d4cc02431a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C31 H26 F N2 O P Pd'
_chemical_formula_sum            'C31 H26 F N2 O P Pd'
_chemical_formula_weight         598.91
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2024-03-19
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-04-06 deposited with the CCDC.	2024-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                73.358(3)
_cell_angle_beta                 74.524(3)
_cell_angle_gamma                66.061(3)
_cell_formula_units_Z            2
_cell_length_a                   9.6832(8)
_cell_length_b                   11.7011(9)
_cell_length_c                   13.0161(10)
_cell_measurement_reflns_used    2505
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.82
_cell_measurement_theta_min      2.45
_cell_volume                     1272.21(18)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.1798
_diffrn_reflns_av_unetI/netI     0.1170
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            36104
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.158
_diffrn_reflns_theta_min         2.286
_exptl_absorpt_coefficient_mu    0.828
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6419
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1032 before and 0.0882 after correction.
The Ratio of minimum to maximum transmission is 0.8603.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_recrystallization_method 'cooling in toluene'
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.795
_refine_diff_density_min         -0.855
_refine_diff_density_rms         0.148
_refine_ls_extinction_coef       0.0043(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     431
_refine_ls_number_reflns         5083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0602
_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^)+4.5753P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.1095
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3381
_reflns_number_total             5083
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02431a2.cif
_cod_data_source_block           jjl724_clear_cube_0m_a
_cod_depositor_comments
'Adding full bibliography for 7133373--7133374.cif.'
_cod_database_code               7133373
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.968
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C15(H15)
;
_shelx_res_checksum              84962
_shelx_hkl_checksum              24310
_olex2_submission_special_instructions 'No special instructions were received'