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_4513911
_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         'C18 H18 Cl2 Pd2'
_chemical_formula_sum            'C18 H18 Cl2 Pd2'
_chemical_formula_weight         518.00
_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                 90.274(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1578(3)
_cell_length_b                   10.4643(4)
_cell_length_c                   16.6141(5)
_cell_measurement_reflns_used    3541
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.629
_cell_measurement_theta_min      6.641
_cell_volume                     1765.96(10)
_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      100.0
_diffrn_measured_fraction_theta_full 0.921
_diffrn_measured_fraction_theta_max 0.921
_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  0.0503
_diffrn_reflns_av_unetI/netI     0.0709
_diffrn_reflns_Laue_measured_fraction_full 0.921
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6312
_diffrn_reflns_point_group_measured_fraction_full 0.921
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        66.672
_diffrn_reflns_theta_max         66.672
_diffrn_reflns_theta_min         6.641
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    19.142
_exptl_absorpt_correction_T_max  0.3808
_exptl_absorpt_correction_T_min  0.1744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1235 before and 0.0657 after correction.
The Ratio of minimum to maximum transmission is 0.4580.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.937
_exptl_crystal_description       plate
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.587
_refine_diff_density_min         -2.553
_refine_diff_density_rms         0.302
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0711
_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^)+(0.1168P)^2^+11.9401P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1895
_refine_ls_wR_factor_ref         0.1959
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2578
_reflns_number_total             2885
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b01818_si_002.cif
_cod_data_source_block           cu_vsr1_0m
_cod_depositor_comments
'Adding full bibliography for 4513910--4513911.cif.'
_cod_original_formula_moiety     'C18 H15 Cl2 Pd2'
_cod_original_formula_sum        'C18 H15 Cl2 Pd2'
_cod_original_formula_weight     515.00
_cod_database_code               4513911
_shelx_estimated_absorpt_t_max   0.515
_shelx_estimated_absorpt_t_min   0.108
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C006(H006), C007(H007)
2.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C005(H005), C00A(H00C), C00B(H00D), C00C(H00E), C00D(H00F), C00F(H00G),
 C1AA(H1AA), C6(H6), C1(H1), C2(H2), C3(H3)
2.d Fitted hexagon refined as free rotating group:
 C1AA(C3AA,C6,C1,C2,C3)
;
_shelx_res_checksum              13914
_shelx_hkl_checksum              82105
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'