Palladium-NHC (NHC = N-heterocyclic Carbene)-Catalyzed Suzuki–Miyaura Cross-Coupling of Alkyl Amides
Wang, Chang-An; Rahman, Md. Mahbubur; Bisz, Elwira; Dziuk, Błażej; Szostak, Roman; Szostak, Michal; ACS Catalysis 12 (2022) 2426–2433; doi:10.1021/acscatal.1c05738

data_4519342
_publ_section_title
;
 Palladium-NHC (NHC = N-heterocyclic Carbene)-Catalyzed Suzuki--Miyaura
 Cross-Coupling of Alkyl Amides
;
_journal_issue                   4
_journal_name_full               'ACS Catalysis'
_journal_page_first              2426
_journal_page_last               2433
_journal_paper_doi               10.1021/acscatal.1c05738
_journal_volume                  12
_journal_year                    2022
_chemical_formula_sum            'C16 H17 N3 O3'
_chemical_formula_weight         299.32
_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_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.806(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.5366(15)
_cell_length_b                   9.0589(8)
_cell_length_c                   30.020(3)
_cell_measurement_reflns_used    1705
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.4740
_cell_measurement_theta_min      2.0100
_cell_volume                     3100.4(6)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9718
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'KM4 with Eos CCD'
_diffrn_measurement_method       \w--scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0904
_diffrn_reflns_av_unetI/netI     0.1731
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            11578
_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         25.999
_diffrn_reflns_theta_min         1.813
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SCALE3 ABSPACK (Rigaku Oxford Diffraction, 2015).
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         6087
_refine_ls_number_restraints     384
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.2512
_refine_ls_R_factor_gt           0.1168
_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^)+(0.1347P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2691
_refine_ls_wR_factor_ref         0.3405
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2120
_reflns_number_total             6087
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c05738_si_002.cif
_cod_data_source_block           B18_MR42_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4519342
_shelx_shelxl_version_number     2014/7
_exptl_absorpt_special_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_shelx_res_checksum              46701
_shelx_hkl_checksum              90051