Palladium-catalyzed intramolecular aza-Wacker-type cyclization of vinyl cyclopropanecarboxamides to access conformationally restricted aza[3.1.0]bicycles
Li, Mengjuan; Li, Jingya; Zhang, Zhiguo; Chen, Liming; Ma, Nana; Liu, Qingfeng; Zhang, Xingjie; Zhang, Guisheng; RSC Advances 13 (2023) 27158–27166; doi:10.1039/D3RA05440C

data_7247363
_publ_section_title
;
 Palladium-catalyzed intramolecular aza-Wacker-type cyclization of vinyl
 cyclopropanecarboxamides to access conformationally restricted
 aza[3.1.0]bicycles
;
_journal_issue                   39
_journal_name_full               'RSC Advances'
_journal_page_first              27158
_journal_page_last               27166
_journal_paper_doi               10.1039/D3RA05440C
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C19 H16 Cl N O'
_chemical_formula_sum            'C19 H17 Cl N O'
_chemical_formula_weight         310.79
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-01-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-01-17 deposited with the CCDC.	2023-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                82.729(4)
_cell_angle_beta                 86.836(4)
_cell_angle_gamma                75.912(4)
_cell_formula_units_Z            2
_cell_length_a                   7.0254(3)
_cell_length_b                   8.4668(4)
_cell_length_c                   13.4722(6)
_cell_measurement_reflns_used    12540
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.187
_cell_measurement_theta_min      3.554
_cell_volume                     770.76(6)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  template
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5569
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.540
_diffrn_reflns_theta_min         5.424
_exptl_absorpt_coefficient_mu    2.189
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             326
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2917
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0572P)^2^+0.2986P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1066
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2732
_reflns_number_total             2917
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra05440c2.cif
_cod_data_source_block           ljy-20220115
_cod_database_code               7247363
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.978
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C8(H8), C11(H11), C9(H9), C15(H15), C16(H16), C19(H19), C18(H18)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              14732
_olex2_submission_special_instructions 'No special instructions were received'