Polycyclic Azetidines and Pyrrolidines via Palladium-Catalyzed Intramolecular Amination of Unactivated C(sp3)-H Bonds.
Zhao, Jie; Zhao, Xiao-Jing; Cao, Pei; Liu, Ji-Kai; Wu, Bin; Organic letters 19 (2017) 4880–4883; doi:10.1021/acs.orglett.7b02339

data_1547582
_publ_section_title
;
 Polycyclic Azetidines and Pyrrolidines via Palladium-Catalyzed
 Intramolecular Amination of Unactivated C(sp3)-H Bonds.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4880
_journal_page_last               4883
_journal_paper_doi               10.1021/acs.orglett.7b02339
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C19 H19 Br N2 O'
_chemical_formula_sum            'C19 H19 Br N2 O'
_chemical_formula_weight         371.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.3885(17)
_cell_length_b                   7.1222(8)
_cell_length_c                   30.300(4)
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.43
_cell_measurement_theta_min      2.69
_cell_volume                     3320.9(7)
_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 0.998
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            34774
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.041
_diffrn_reflns_theta_min         1.344
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_description       prism
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.860
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.130
_exptl_transmission_factor_max   0.7462
_exptl_transmission_factor_min   0.4667
_refine_diff_density_max         5.967
_refine_diff_density_min         -1.162
_refine_diff_density_rms         0.197
_refine_ls_abs_structure_details
;
 Flack x determined using 3375 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.539(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         9808
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0721
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1153P)^2^+12.4834P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1829
_refine_ls_wR_factor_ref         0.1948
_reflns_Friedel_coverage         0.910
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.893
_reflns_number_gt                8242
_reflns_number_total             9808
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02339_si_003.cif
_cod_data_source_block           mo_bwje155_0m
_cod_original_cell_volume        3320.9(6)
_cod_database_code               1547582
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.224
_shelx_estimated_absorpt_t_max   0.739
_shelx_res_checksum              71086
_shelx_hkl_checksum              82427