Chiral Pyridinium Phosphoramide as a Dual Brønsted Acid Catalyst for Enantioselective Diels-Alder Reaction.
Nishikawa, Yasuhiro; Nakano, Saki; Tahira, Yuu; Terazawa, Kanako; Yamazaki, Ken; Kitamura, Chitoshi; Hara, Osamu; Organic letters 18 (2016) 2004–2007; doi:10.1021/acs.orglett.6b00608

data_1543141
_publ_section_title
;
 Chiral Pyridinium Phosphoramide as a Dual Br\/onsted Acid Catalyst for
 Enantioselective Diels-Alder Reaction.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2004
_journal_page_last               2007
_journal_paper_doi               10.1021/acs.orglett.6b00608
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety
'(C50 H36 N2 O4 P1 +), (C1 F3 O3 S1 -), (C1 H2 Cl2)'
_chemical_formula_sum            'C52 H38 Cl2 F3 N2 O7 P S'
_chemical_formula_weight         993.77
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_cell_angle_alpha                71.074(5)
_cell_angle_beta                 67.743(5)
_cell_angle_gamma                66.374(5)
_cell_formula_units_Z            2
_cell_length_a                   13.4369(10)
_cell_length_b                   13.7007(9)
_cell_length_c                   15.4740(11)
_cell_measurement_reflns_used    15005
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.01
_cell_measurement_wavelength     0.71073
_cell_volume                     2364.9(3)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR-2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'RIGAKU RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.1015
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22633
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.474
_diffrn_reflns_theta_min         3.008
_diffrn_source                   'fine-focus sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.815
_refine_diff_density_rms         0.07
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     627
_refine_ls_number_reflns         10597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1179
_refine_ls_R_factor_gt           0.0713
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1142P)^2^+1.1390P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1896
_refine_ls_wR_factor_ref         0.2196
_reflns_Friedel_coverage         0
_reflns_number_gt                6615
_reflns_number_total             10597
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00608_si_002.cif
_cod_data_source_block           PPA
_cod_depositor_comments          'Adding full bibliography for 1543141.cif.'
_cod_database_code               1543141
_shelx_estimated_absorpt_t_min   0.86
_shelx_estimated_absorpt_t_max   0.933
_shelx_res_checksum              64750
_shelx_hkl_checksum              92555