Palladium/silver co-catalyzed syn-stereoselective asymmetric ring-opening reactions of azabenzonorbornadienes with amides
Shen, Guoli; Khan, Ruhima; Lv, Haiping; Yang, Yong; Zhang, Xia; Zhan, Yong; Zhou, Yongyun; Fan, Baomin; Organic Chemistry Frontiers 6 (2019) 1423–; doi:10.1039/C9QO00041K

data_1554709
_publ_section_title
;
 Palladium/silver co-catalyzed syn-stereoselective asymmetric ring-opening
 reactions of azabenzonorbornadienes with amides
;
_journal_issue                   9
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1423
_journal_paper_doi               10.1039/C9QO00041K
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H23 Br N2 O4 S'
_chemical_formula_sum            'C21 H23 Br N2 O4 S'
_chemical_formula_weight         479.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-09-27 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4007(2)
_cell_length_b                   10.8468(2)
_cell_length_c                   21.7267(5)
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.23
_cell_measurement_theta_min      4.07
_cell_volume                     2215.42(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.972
_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  0.0426
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13347
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.227
_diffrn_reflns_theta_min         4.069
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       prism
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.710
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_transmission_factor_max   0.2751
_exptl_transmission_factor_min   0.0729
_refine_diff_density_max         0.904
_refine_diff_density_min         -0.872
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 1414 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.089(6)
_refine_ls_extinction_coef       0.0033(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0476P)^2^+1.5272P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0946
_reflns_Friedel_coverage         0.616
_reflns_Friedel_fraction_full    0.838
_reflns_Friedel_fraction_max     0.801
_reflns_number_gt                3787
_reflns_number_total             3808
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00041k2.cif
_cod_data_source_block           cu_qsgl359b2_0m
_cod_database_code               1554709
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.181
_shelx_estimated_absorpt_t_max   0.500
_shelx_res_checksum              96359
_shelx_hkl_checksum              51591