Pd(0)-Catalyzed Alkenylation and Allylic Dearomatization Reactions between Nucleophile-Bearing Indoles and Propargyl Carbonate.
Gao, Run-Duo; Liu, Chuan; Dai, Li-Xin; Zhang, Wei; You, Shu-Li; Organic letters 16 (2014) 3919–3921; doi:10.1021/ol501704q

data_1516811
_publ_section_title
;
 Pd(0)-Catalyzed Alkenylation and Allylic Dearomatization Reactions
 between Nucleophile-Bearing Indoles and Propargyl Carbonate.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3919
_journal_page_last               3921
_journal_paper_doi               10.1021/ol501704q
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H22 Br N O5'
_chemical_formula_weight         436.29
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 106.962(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.9109(11)
_cell_length_b                   13.975(2)
_cell_length_c                   10.4052(16)
_cell_measurement_reflns_used    1572
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      41.893
_cell_measurement_theta_min      5.023
_cell_volume                     961.2(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
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_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5535
_diffrn_reflns_point_group_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.488
_diffrn_reflns_theta_min         2.046
_exptl_absorpt_coefficient_mu    2.169
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.110
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_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details
; 
 Flack x determined using 1054 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.145(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3357
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0567
_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^)+(0.0937P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1530
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    0.878
_reflns_Friedel_fraction_max     0.876
_reflns_number_gt                2778
_reflns_number_total             3357
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol501704q_si_002.cif
_cod_data_source_block           cd214384
_cod_depositor_comments          'Adding full bibliography for 1516811.cif.'
_cod_original_cell_volume        961.3(3)
_cod_database_code               1516811
_shelxl_version_number           2013-4
_shelx_res_checksum              28541
_shelx_hkl_checksum              66595