Chiral Diphosphine-Palladium-Catalyzed Sequential Asymmetric Double-Friedel-Crafts Alkylation and N-Hemiketalization for Spiro-polycyclic Indole Derivatives.
Li, Nai-Kai; Zhang, Jun-Qi; Sun, Bing-Bing; Li, Hai-Yan; Wang, Xing-Wang; Organic letters 19 (2017) 1954–1957; doi:10.1021/acs.orglett.7b00368

data_1545744
_publ_section_title
;
 Chiral Diphosphine-Palladium-Catalyzed Sequential Asymmetric
 Double-Friedel-Crafts Alkylation and N-Hemiketalization for
 Spiro-polycyclic Indole Derivatives.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1954
_journal_page_last               1957
_journal_paper_doi               10.1021/acs.orglett.7b00368
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C33 H27 Cl5 N3 O3 D'
_chemical_formula_sum            'C33 H26 Cl5 D N3 O3'
_chemical_formula_weight         692.86
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.2146(10)
_cell_length_b                   22.5610(14)
_cell_length_c                   9.2044(6)
_cell_measurement_reflns_used    6787
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.39
_cell_volume                     3367.1(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_sigmaI/netI    0.1144
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9643
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.468
_exptl_absorpt_correction_T_max  0.9288
_exptl_absorpt_correction_T_min  0.8348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.747
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.115
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(17)
_refine_ls_extinction_coef       0.020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         6192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1666
_refine_ls_R_factor_gt           0.0981
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1779P)^2^+0.5324P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2699
_refine_ls_wR_factor_ref         0.3119
_reflns_number_gt                3453
_reflns_number_total             6192
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b00368_si_002.cif
_cod_data_source_block           b161021a_0ma_a
_cod_depositor_comments          'Adding full bibliography for 1545744.cif.'
_cod_original_formula_sum        'C33 H26 Cl5 N3 O3 D'
_cod_database_code               1545744