Novel binaphthyl and biphenyl α- and β-amino acids and esters: organocatalysis of asymmetric Diels-Alder reactions. A combined synthetic and computational study.
Bulman Page, Philip C.; Kinsey, Francesca S.; Chan, Yohan; Strutt, Ian R.; Slawin, Alexandra M. Z.; Jones, Garth A.; Organic & biomolecular chemistry 16 (2018) 7400–7416; doi:10.1039/c8ob01795f

data_7156432
_publ_section_title
;
 Novel binaphthyl and biphenyl \a- and \b-amino acids and esters:
 organocatalysis of asymmetric Diels-Alder reactions. A combined synthetic
 and computational study.
;
_journal_issue                   40
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7400
_journal_page_last               7416
_journal_paper_doi               10.1039/c8ob01795f
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H31 N O2'
_chemical_formula_sum            'C31 H31 N O2'
_chemical_formula_weight         449.59
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-12
_audit_creation_method           'by CrystalStructure 4.2'
_audit_update_record
;
2018-07-25 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 113.247(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   8.0982(7)
_cell_length_b                   16.4309(13)
_cell_length_c                   10.0674(8)
_cell_measurement_reflns_used    6307
_cell_measurement_temperature    125
_cell_measurement_theta_max      67.36
_cell_measurement_theta_min      4.76
_cell_volume                     1230.82(18)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r2'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r2'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      125
_diffrn_detector_area_resol_mean 29.257
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_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            14497
_diffrn_reflns_point_group_measured_fraction_full 0.894
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         67.709
_diffrn_reflns_theta_min         4.781
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             480.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.20
_refine_ls_abs_structure_details
;
 Flack x determined using 1311 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3976
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0563
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0176P)^2^+0.9893P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0986
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_full    0.817
_reflns_Friedel_fraction_max     0.816
_reflns_number_gt                3554
_reflns_number_total             3976
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c8ob01795f3.cif
_cod_data_source_block           +28
_cod_depositor_comments
'Adding full bibliography for 7156430--7156433.cif.'
_cod_database_code               7156432
_shelx_res_checksum              77577