Enantioselective synthesis of fused heterocycles with contiguous stereogenic centers by chiral phosphoric acid catalyzed symmetry breaking
Keiji Mori; Ayaka Miyake; Takahiko Akiyama; Chem.Commun. 51 (2015) 16107–; doi:10.1039/C5cc05508C

data_7118011
_publ_section_title
;
 Enantioselective synthesis of fused heterocycles with contiguous
 stereogenic centers by chiral phosphoric acid catalyzed symmetry breaking
;
_journal_name_full               Chem.Commun.
_journal_page_first              16107
_journal_paper_doi               10.1039/C5cc05508C
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H22 Br N O3'
_chemical_formula_weight         476.35
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-05-08 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                71.7010(10)
_cell_angle_beta                 89.752(2)
_cell_angle_gamma                81.716(2)
_cell_formula_units_Z            1
_cell_length_a                   6.2811(10)
_cell_length_b                   7.9645(12)
_cell_length_c                   11.2853(18)
_cell_measurement_temperature    90
_cell_volume                     529.91(14)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHELL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5764
_diffrn_reflns_point_group_measured_fraction_full 0.915
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.438
_diffrn_reflns_theta_min         1.902
_exptl_absorpt_coefficient_mu    1.968
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_description       block
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1902 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.041(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.675
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4318
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.674
_refine_ls_R_factor_all          0.0195
_refine_ls_R_factor_gt           0.0193
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0469
_refine_ls_wR_factor_ref         0.0470
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_full    0.838
_reflns_Friedel_fraction_max     0.807
_reflns_number_gt                4274
_reflns_number_total             4318
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc05508c2.cif
_cod_data_source_block           shelxl2_a
_cod_database_code               7118011
_shelx_estimated_absorpt_t_min   0.827
_shelx_estimated_absorpt_t_max   0.827
_shelxl_version_number           2014/6
_shelx_res_checksum              2086