Pd-catalyzed stereoselective tandem ring-opening amination/cyclization of vinyl gamma-lactones: Access to caprolactam diversity
Xie, Jianing; Li, Xuetong; Kleij, Arjan Willem; Chemical Science  (2020) –; doi:10.1039/D0SC03647A

data_1558807
_publ_section_title
;
 Pd-catalyzed stereoselective tandem ring-opening amination/cyclization of
 vinyl gamma-lactones: Access to caprolactam diversity
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC03647A
_journal_year                    2020
_chemical_formula_sum            'C18 H17 Br2 N O'
_chemical_formula_weight         423.14
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-05-05 deposited with the CCDC.	2020-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.551(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0644(10)
_cell_length_b                   7.0550(6)
_cell_length_c                   17.3068(15)
_cell_measurement_reflns_used    4538
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.70
_cell_measurement_theta_min      2.36
_cell_volume                     1590.1(2)
_computing_cell_refinement       'Bruker APEX2 v2014.9-0'
_computing_data_collection       'Bruker APEX2 v2014.9-0'
_computing_data_reduction        'Bruker APEX2 v2014.9-0'
_computing_molecular_graphics
'shelXle (H\"ubschle, Sheldrick and Dittirch, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13440
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.038
_diffrn_reflns_theta_min         1.883
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_current           0.6
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Bruker APEX DUO'
_exptl_absorpt_coefficient_mu    5.099
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.1854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/4
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.220
_refine_diff_density_max         1.290
_refine_diff_density_min         -1.273
_refine_diff_density_rms         0.149
_refine_ls_extinction_coef       0.0033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         4162
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0425P)^2^+0.0939P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0979
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3363
_reflns_number_total             4162
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc03647a2.cif
_cod_data_source_block           mo_JN236_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1558807
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.166
_shelx_estimated_absorpt_t_max   0.400
_shelx_res_checksum              44746