Palladium-Catalyzed Enantioselective Domino Heck/Intermolecular C-H Bond Functionalization: Development and Application to the Synthesis of (+)-Esermethole.
Kong, Wangqing; Wang, Qian; Zhu, Jieping; Journal of the American Chemical Society 137 (2015) 16028–16031; doi:10.1021/jacs.5b11625

data_4124825
_publ_section_title
;
 Palladium-Catalyzed Enantioselective Domino Heck/Intermolecular C-H Bond
 Functionalization: Development and Application to the Synthesis of
 (+)-Esermethole.
;
_journal_issue                   51
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16028
_journal_page_last               16031
_journal_paper_doi               10.1021/jacs.5b11625
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C25 H20 Br N3 O2'
_chemical_formula_sum            'C25 H20 Br N3 O2'
_chemical_formula_weight         474.35
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-10-23 # Formatted by publCIF

;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.87(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.862(2)
_cell_length_b                   8.9413(18)
_cell_length_c                   44.757(9)
_cell_measurement_reflns_used    173
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22
_cell_measurement_theta_min      3
_cell_volume                     4315.6(15)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs, 1990-2000)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0646
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_number            46444
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.37
_exptl_absorpt_coefficient_mu    1.932
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2008, Bruker AXS, 2008'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.16
_refine_diff_density_max         6.281
_refine_diff_density_min         -0.934
_refine_diff_density_rms         0.246
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_extinction_coef       0.0039(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1129
_refine_ls_number_reflns         17585
_refine_ls_number_restraints     721
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0919
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1586P)^2^+4.9482P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2181
_refine_ls_wR_factor_ref         0.2303
_reflns_number_gt                16290
_reflns_number_total             17585
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b11625_si_001.cif
_cod_data_source_block           kwq-c-48b
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4124825
_publcif_datablock.id            {58017060-3e8f-4da1-b554-17d5d44cf15a}
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n