Enantioselective synthesis of N-allylindoles via palladium-catalyzed allylic amination/oxidation of indolines
Zhao, Qiang; Zhuo, Chun-Xiang; You, Shu-Li; RSC Advances 4 (2014) 10875–; doi:10.1039/c4ra00701h

data_7235504
_publ_section_title
;
 Enantioselective synthesis of N-allylindoles via palladium-catalyzed
 allylic amination/oxidation of indolines
;
_journal_issue                   21
_journal_name_full               'RSC Advances'
_journal_page_first              10875
_journal_paper_doi               10.1039/c4ra00701h
_journal_volume                  4
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H19 N'
_chemical_formula_weight         309.39
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 98.145(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.5200(2)
_cell_length_b                   5.8727(2)
_cell_length_c                   16.9410(5)
_cell_measurement_reflns_used    4577
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      5.24
_cell_volume                     839.10(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8656
_diffrn_reflns_theta_full        69.93
_diffrn_reflns_theta_max         69.93
_diffrn_reflns_theta_min         5.24
_exptl_absorpt_coefficient_mu    0.537
_exptl_absorpt_correction_T_max  0.9893
_exptl_absorpt_correction_T_min  0.9002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2875
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+0.0686P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0907
_reflns_number_gt                2755
_reflns_number_total             2875
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra00701h2.cif
_cod_data_source_block           cu_dm12452_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7235504