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_7133374
_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 Cl N2 O P Pd, 1[C4H8O2]'
_chemical_formula_sum            'C35 H34 Cl N2 O3 P Pd'
_chemical_formula_weight         703.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_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
;
2024-04-10 deposited with the CCDC.	2024-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.551(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0260(6)
_cell_length_b                   16.8504(11)
_cell_length_c                   17.4371(11)
_cell_measurement_reflns_used    9485
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.37
_cell_volume                     3194.8(3)
_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 0.998
_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  0.0770
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            61357
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.315
_diffrn_reflns_theta_min         2.043
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6454
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.764
_refine_diff_density_min         -1.111
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         7953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0573P)^2^+10.1638P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1405
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5834
_reflns_number_total             7953
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02431a2.cif
_cod_data_source_block           jjl694_org_colorless_0m_a
_cod_depositor_comments
'Adding full bibliography for 7133373--7133374.cif.'
_cod_database_code               7133374
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.929
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00Z(H00Z), C00V(H00V), C00U(H00U), C00X(H00X), C00W(H00W),
 C00H(H00H), C00I(H00I), C00G(H00G), C00K(H00K), C00J(H00J), C00N(H00N),
 C00L(H00L), C00P(H00P), C00O(H00O), C00S(H00S), C00Q(H00Q), C00R(H00R),
 C00T(H00T), C00F(H00F), C00B(H00C), C010(H010), C011(H011), C012(H012)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 208 electrons were 
found in a volume of 812\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
1[C4H8O2] per Asymmetric Unit 
which account for 192 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              47034
_shelx_hkl_checksum              32946
_shelx_fab_checksum              64524
_olex2_submission_special_instructions 'No special instructions were received'