Enantioselective aza-Friedel-Crafts reaction of furan with α-ketimino esters induced by a conjugated double hydrogen bond network of chiral bis(phosphoric acid) catalysts.
Hatano, Manabu; Okamoto, Haruka; Kawakami, Taro; Toh, Kohei; Nakatsuji, Hidefumi; Sakakura, Akira; Ishihara, Kazuaki; Chemical science 9 (2018) 6361–6367; doi:10.1039/c8sc02290a

data_1549591
_publ_section_title
;
 Enantioselective aza-Friedel-Crafts reaction of furan with \a-ketimino
 esters induced by a conjugated double hydrogen bond network of chiral
 bis(phosphoric acid) catalysts.
;
_journal_issue                   30
_journal_name_full               'Chemical science'
_journal_page_first              6361
_journal_page_last               6367
_journal_paper_doi               10.1039/c8sc02290a
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration (R)
_chemical_formula_sum            'C32 H27 Cl3 N2 O7 S'
_chemical_formula_weight         689.96
_chemical_name_common
'ethyl (R)-6-methoxy-2-oxo-4-(1-tosyl-1H-indol-2-yl)-3,4-dihydro-2H-naphtho[2,1-e][1,3]oxazine-4-carboxylate'
_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   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2016-12-04 deposited with the CCDC.
2018-06-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.778(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.664(3)
_cell_length_b                   10.372(2)
_cell_length_c                   14.789(4)
_cell_measurement_reflns_used    5627
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.00
_cell_volume                     1581.7(7)
_computing_cell_refinement       'Rigaku CrystalClear'
_computing_data_collection       'Rigaku CrystalClear'
_computing_data_reduction        'Rigaku CrystalClear'
_computing_molecular_graphics    'Rigaku CrystalStructure'
_computing_publication_material  'Rigaku CrystalStructure'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'Rigaku CrystalStructure'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'PILATUS 200K area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13598
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.025
_exptl_absorpt_coefficient_mu    0.407
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Rigaku CrystalClear'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.750
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   1.000
_exptl_transmission_factor_min   0.854
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 2750 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         6894
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0318
_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^)+(0.0476P)^2^+0.3226P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0814
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_full    0.928
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                6403
_reflns_number_total             6894
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc02290a2.cif
_cod_data_source_block           CrystalClear
_cod_depositor_comments
'Adding full bibliography for 1549591--1549594.cif.'
_cod_database_code               1549591
_shelx_estimated_absorpt_t_min   0.750
_shelx_estimated_absorpt_t_max   0.960
_shelxl_version_number           2014/6
_shelx_res_checksum              61689