Pd-catalyzed arylation/aza-Michael addition cascade to C2-spiroindolines and azabicyclo[3.2.2]nonanones.
Zhang, Xiao-Wen; Zhang, Hui; Wang, Hu-Chong; Zhu, Ming-Hui; Cong, Hengjiang; Liu, Wen-Bo; Chemical communications (Cambridge, England) 56 (2020) 12013–12016; doi:10.1039/d0cc04935b

data_7127145
_publ_section_title
;
 Pd-catalyzed arylation/aza-Michael addition cascade to C2-spiroindolines
 and azabicyclo[3.2.2]nonanones.
;
_journal_issue                   80
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12013
_journal_page_last               12016
_journal_paper_doi               10.1039/d0cc04935b
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H27 N O'
_chemical_formula_weight         381.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2019-03-26 deposited with the CCDC.	2020-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.759(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7872(5)
_cell_length_b                   16.2182(8)
_cell_length_c                   9.4765(4)
_cell_measurement_reflns_used    4041
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.45
_cell_measurement_theta_min      4.23
_cell_volume                     2104.25(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Kappa APEX-Duo CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5476
_diffrn_reflns_point_group_measured_fraction_full 0.755
_diffrn_reflns_point_group_measured_fraction_max 0.755
_diffrn_reflns_theta_full        66.443
_diffrn_reflns_theta_max         66.443
_diffrn_reflns_theta_min         4.226
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.555
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker,2012)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 896 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2802
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0759P)^2^+0.1062P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1063
_reflns_Friedel_coverage         0.518
_reflns_Friedel_fraction_full    0.516
_reflns_Friedel_fraction_max     0.516
_reflns_number_gt                2726
_reflns_number_total             2802
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04935b2.cif
_cod_data_source_block           x_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7127144--7127145.cif.
;
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7127145
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.936
_shelx_estimated_absorpt_t_max   0.978
_shelx_res_checksum              85155
_shelx_hkl_checksum              88581