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_1558806
_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 N O'
_chemical_formula_weight         263.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-04-21 deposited with the CCDC.	2020-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.545(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2396(2)
_cell_length_b                   23.7102(7)
_cell_length_c                   9.2667(3)
_cell_measurement_reflns_used    7760
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.3550
_cell_measurement_theta_min      2.7680
_cell_volume                     1362.00(7)
_computing_cell_refinement
'CrysAlisPro 1.171.40.53 64bit (Rigaku OD, 2019)'
_computing_data_collection
'CrysAlisPro 1.171.40.53 64bit (Rigaku OD, 2019)'
_computing_data_reduction
'CrysAlisPro 1.171.40.53 64bit (Rigaku OD, 2019)'
_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    Sir2019
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12489
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.432
_diffrn_reflns_theta_min         2.373
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_current           24
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       Block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3456
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0567P)^2^+0.3991P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1088
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3098
_reflns_number_total             3456
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc03647a2.cif
_cod_data_source_block           JN181
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1558806
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              4501