Palladium-Catalyzed Allylic Amidation with N-Heterocycles via sp3C‒H Oxidation
Vemula, Sandeep R.; Kumar, Dinesh; Cook, Gregory R.; ACS Catalysis 6 (2016) 5295–; doi:10.1021/acscatal.6b01818

data_4513910
_publ_section_title
;
 Palladium-Catalyzed Allylic Amidation with N-Heterocycles via sp3C--H
 Oxidation
;
_journal_issue                   8
_journal_name_full               'ACS Catalysis'
_journal_page_first              5295
_journal_paper_doi               10.1021/acscatal.6b01818
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C4 H12 Cl2 O2 Pd S2'
_chemical_formula_sum            'C4 H12 Cl2 O2 Pd S2'
_chemical_formula_weight         333.56
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-02-18
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.635(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.2660(4)
_cell_length_b                   9.3515(5)
_cell_length_c                   9.3563(5)
_cell_measurement_reflns_used    4556
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.757
_cell_measurement_theta_min      4.989
_cell_volume                     519.50(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4691
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.752
_diffrn_reflns_theta_max         66.752
_diffrn_reflns_theta_min         6.882
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    22.558
_exptl_absorpt_correction_T_max  0.1204
_exptl_absorpt_correction_T_min  0.0254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1208 before and 0.0772 after correction. The Ratio of minimum to maximum transmission is 0.2110. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.132
_exptl_crystal_description       irregular
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.316
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.182
_refine_diff_density_max         0.876
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     54
_refine_ls_number_reflns         914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0541P)^2^+0.8663P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0934
_reflns_Friedel_coverage         0.000
_reflns_number_gt                908
_reflns_number_total             914
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b01818_si_003.cif
_cod_data_source_block           cu_vsr2_0m
_cod_depositor_comments
'Adding full bibliography for 4513910--4513911.cif.'
_cod_database_code               4513910
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C005(H00A,H00B,H00C), C006(H00D,H00E,H00F)
;
_shelx_res_checksum              67360
_shelx_hkl_checksum              19029
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'