Enantioselective Pd(II)-Catalyzed Intramolecular Oxidative 6- endo Aminoacetoxylation of Unactivated Alkenes.
Qi, Xiaoxu; Chen, Chaohuang; Hou, Chuanqi; Fu, Liang; Chen, Pinhong; Liu, Guosheng; Journal of the American Chemical Society 140 (2018) 7415–7419; doi:10.1021/jacs.8b03767

data_4132419
_publ_section_title
;
 Enantioselective Pd(II)-Catalyzed Intramolecular Oxidative 6- endo
 Aminoacetoxylation of Unactivated Alkenes.
;
_journal_issue                   24
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7415
_journal_page_last               7419
_journal_paper_doi               10.1021/jacs.8b03767
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C27 H22 Cl2 N2 O Pd'
_chemical_formula_sum            'C27 H22 Cl2 N2 O Pd'
_chemical_formula_weight         567.76
_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_Hall           'P 65'
_space_group_name_H-M_alt        'P 65'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-08-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   20.913(6)
_cell_length_b                   20.913(6)
_cell_length_c                   10.050(3)
_cell_measurement_reflns_used    3747
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.404
_cell_measurement_theta_min      2.316
_cell_volume                     3806.5(19)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.886
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1111
_diffrn_reflns_av_unetI/netI     0.1355
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.886
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16966
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.565
_diffrn_reflns_theta_min         2.811
_exptl_absorpt_coefficient_mu    0.963
_exptl_absorpt_correction_T_max  0.2617
_exptl_absorpt_correction_T_min  0.2173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1132 before and 0.0753 after correction. The Ratio of minimum to maximum transmission is 0.8303. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_description       block
_exptl_crystal_F_000             1716
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.683
_refine_diff_density_rms         0.132
_refine_ls_abs_structure_details
;
 Flack x determined using 1118 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4920
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0599
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0411P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1236
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    0.952
_reflns_Friedel_fraction_max     0.785
_reflns_number_gt                3372
_reflns_number_total             4920
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b03767_si_003.cif
_cod_data_source_block           mo_d8v17272_0m
_cod_original_cell_volume        3807(2)
_cod_database_code               4132419
_shelx_shelxl_version_number     2014/8
_shelx_estimated_absorpt_t_max   0.901
_shelx_estimated_absorpt_t_min   0.831
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O1) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C8(H8), C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C17(H17A,H17B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C18(H18),
 C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
;
_shelx_res_checksum              46923
_shelx_hkl_checksum              53192
_shelx_fab_checksum              94011
_olex2_submission_special_instructions 'No special instructions were received'