Convergent Azaspirocyclization of Bromoarenes with N-Tosylhydrazones by a Palladium Catalyst
Yanagimoto, Aika; Uwabe, Yota; Wu, Qikun; Muto, Kei; Yamaguchi, Junichiro; ACS Catalysis 11 (2021) 10429–10435; doi:10.1021/acscatal.1c02627

data_4518979
_publ_section_title
;
 Convergent Azaspirocyclization of Bromoarenes with N-Tosylhydrazones by a
 Palladium Catalyst
;
_journal_issue                   16
_journal_name_full               'ACS Catalysis'
_journal_page_first              10429
_journal_page_last               10435
_journal_paper_doi               10.1021/acscatal.1c02627
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C20 H17 N O2'
_chemical_formula_sum            'C20 H17 N O2'
_chemical_formula_weight         303.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-04
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.5675(11)
_cell_length_b                   15.2858(15)
_cell_length_c                   18.2662(17)
_cell_measurement_reflns_used    19355
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      136.48
_cell_measurement_theta_min      7.54
_cell_volume                     3229.8(5)
_computing_cell_refinement       'Rigaku RAPID-AUTO'
_computing_data_collection       'Rigaku RAPID-AUTO'
_computing_data_reduction        'Rigaku RAPID-AUTO'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
;
Rigaku R-AXIS RAPID-II with Ultrax 18
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            34384
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         68.242
_diffrn_reflns_theta_min         4.842
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.8442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2946
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0420P)^2^+0.9164P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0908
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2689
_reflns_number_total             2946
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c02627_si_002.cif
_cod_data_source_block           9Aa
_cod_database_code               4518979
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C20(H20), C10(H10), C11(H11), C13(H13), C12(H12), C16(H16), C8(H8),
 C19(H19), C7(H7), C18(H18), C17(H17)
;
_shelx_res_checksum              48036
_shelx_hkl_checksum              86903
_olex2_submission_special_instructions 'No special instructions were received'