Dual-Functional Enone-Directing Group/Electrophile for Sequential C–C Bond Formation with α-Diazomalonates: A Short Synthesis of Chiral 3,4-Fused Tricyclic Indoles
Harada, Shingo; Yanagawa, Mai; Nemoto, Tetsuhiro; ACS Catalysis  (2020) 11971–11979; doi:10.1021/acscatal.0c03940

data_4518103
_publ_section_title
;
 Dual-Functional Enone-Directing Group/Electrophile for Sequential C--C
 Bond Formation with \a-Diazomalonates: A Short Synthesis of Chiral
 3,4-Fused Tricyclic Indoles
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              11971
_journal_page_last               11979
_journal_paper_doi               10.1021/acscatal.0c03940
_journal_year                    2020
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C25 H25 N O5'
_chemical_formula_sum            'C25 H25 N O5'
_chemical_formula_weight         419.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.940(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   11.5680(3)
_cell_length_b                   14.8438(4)
_cell_length_c                   12.2105(3)
_cell_measurement_reflns_used    15078
_cell_measurement_temperature    93
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      3.84
_cell_volume                     2088.91(10)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23343
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        68.220
_diffrn_reflns_theta_max         68.220
_diffrn_reflns_theta_min         3.633
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_correction_T_min  0.724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             888.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.20
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  3177 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.09(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     559
_refine_ls_number_reflns         7156
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0513P)^2^+0.0098P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1001
_reflns_number_gt                6067
_reflns_number_total             7156
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            cs0c03940_si_002.cif
_cod_data_source_block           20191212mai
_cod_original_cell_volume        2088.91(9)
_cod_database_code               4518103