Chiral N-1-adamantyl-N-trans-cinnamylaniline type ligands: synthesis and application to palladium-catalyzed asymmetric allylic alkylation of indoles.
Mino, Takashi; Nishikawa, Kenji; Asano, Moeko; Shima, Yamato; Ebisawa, Toshibumi; Yoshida, Yasushi; Sakamoto, Masami; Organic & biomolecular chemistry 14 (2016) 7509–7519; doi:10.1039/c6ob01354f

data_7155199
_publ_section_title
;
 Chiral N-1-adamantyl-N-trans-cinnamylaniline type ligands: synthesis and
 application to palladium-catalyzed asymmetric allylic alkylation of
 indoles.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7509
_journal_page_last               7519
_journal_paper_doi               10.1039/c6ob01354f
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C41 H40 N P'
_chemical_formula_weight         577.71
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2016-06-21 deposited with the CCDC.
2016-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.61960(10)
_cell_length_b                   22.1572(2)
_cell_length_c                   26.8016(3)
_cell_measurement_reflns_used    9594
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.2612
_cell_measurement_theta_min      2.5874
_cell_volume                     6306.43(11)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            80975
_diffrn_reflns_theta_full        68.05
_diffrn_reflns_theta_max         68.05
_diffrn_reflns_theta_min         2.59
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.985
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2464
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.146
_refine_ls_abs_structure_details
;
Flack x determined using 4785 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     833
_refine_ls_number_reflns         11447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0765P)^2^+0.8451P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1066
_reflns_number_gt                11015
_reflns_number_total             11447
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01354f2.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 7155198--7155200.cif.'
_cod_database_code               7155199