Dearomative Indole Bisfunctionalization via a Diastereoselective Palladium-Catalyzed Arylcyanation.
Petrone, David A.; Yen, Andy; Zeidan, Nicolas; Lautens, Mark; Organic letters 17 (2015) 4838–4841; doi:10.1021/acs.orglett.5b02403

data_1555311
_publ_section_title
;
 Dearomative Indole Bisfunctionalization via a Diastereoselective
 Palladium-Catalyzed Arylcyanation.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4838
_journal_page_last               4841
_journal_paper_doi               10.1021/acs.orglett.5b02403
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C21 H20 N2 O3'
_chemical_formula_sum            'C21 H20 N2 O3'
_chemical_formula_weight         348.39
_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-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 95.625(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.9575(4)
_cell_length_b                   10.3499(4)
_cell_length_c                   34.9584(14)
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      66.61
_cell_measurement_theta_min      2.54
_cell_volume                     3585.4(2)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Kappa APEX-DIO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            70993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.020
_diffrn_reflns_theta_max         67.020
_diffrn_reflns_theta_min         4.457
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_exptl_absorpt_coefficient_mu    0.705
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.6767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       needle
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         6351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0349P)^2^+1.5015P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0814
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6150
_reflns_number_total             6351
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02403_si_004.cif
_cod_data_source_block           d1591
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1555311
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.832
_shelx_estimated_absorpt_t_max   0.939
_shelx_res_checksum              87294
_shelx_hkl_checksum              72084