Pd-Catalyzed de Novo Assembly of Diversely Substituted Indole-Fused Polyheterocycles.
Wang, Qian; Osipyan, Angelina; Konstantinidou, Markella; Butera, Roberto; Mgimpatsang, Kumchok C.; Shishkina, Svitlana V.; Dömling, Alexander; The Journal of organic chemistry 84 (2019) 12148–12156; doi:10.1021/acs.joc.9b01258

data_4034463
_publ_section_title
;
 Pd-Catalyzed de Novo Assembly of Diversely Substituted Indole-Fused
 Polyheterocycles.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12148
_journal_page_last               12156
_journal_paper_doi               10.1021/acs.joc.9b01258
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C22 H23 N3 O2'
_chemical_formula_weight         361.43
_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-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 100.393(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8798(7)
_cell_length_b                   11.5501(8)
_cell_length_c                   21.2513(19)
_cell_measurement_reflns_used    1662
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.249
_cell_measurement_theta_min      3.448
_cell_volume                     1902.4(3)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_unetI/netI     0.0658
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            20215
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         3.165
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.870
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         5437
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.870
_refine_ls_R_factor_all          0.1459
_refine_ls_R_factor_gt           0.0642
_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^)+(0.0864P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1570
_refine_ls_wR_factor_ref         0.1954
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2281
_reflns_number_total             5437
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01258_si_003.cif
_cod_data_source_block           ad8
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034463
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.985
_shelx_hkl_checksum              28243