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_1549592
_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 (S)
_chemical_formula_sum            'C15 H16 Br N O5'
_chemical_formula_weight         370.20
_chemical_name_common
'Methyl (S)-(1-(3-bromophenyl)-2-hydroxy-1-(5-methoxyfuran-2-yl)ethyl)carbamate'
_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
;
2018-04-04 deposited with the CCDC.
2018-06-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.654(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.8577(16)
_cell_length_b                   14.389(4)
_cell_length_c                   9.621(3)
_cell_measurement_reflns_used    3310
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.486
_cell_measurement_theta_min      3.767
_cell_volume                     808.2(4)
_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      103(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.983
_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  0.0284
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6877
_diffrn_reflns_point_group_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         3.490
_exptl_absorpt_coefficient_mu    2.565
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Rigaku CrystalClear'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_transmission_factor_max   1.000
_exptl_transmission_factor_min   0.854
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 951 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.826
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3178
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.826
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0248
_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^)+(0.0169P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0504
_refine_ls_wR_factor_ref         0.0508
_reflns_Friedel_coverage         0.670
_reflns_Friedel_fraction_full    0.768
_reflns_Friedel_fraction_max     0.713
_reflns_number_gt                2589
_reflns_number_total             3178
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc02290a2.cif
_cod_data_source_block           CrystalClear_CCDC1
_cod_depositor_comments
'Adding full bibliography for 1549591--1549594.cif.'
_cod_database_code               1549592
_shelx_estimated_absorpt_t_min   0.467
_shelx_estimated_absorpt_t_max   0.566
_shelxl_version_number           2014/6
_shelx_res_checksum              51034