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_7156433
_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         'C24 H19 N O2'
_chemical_formula_sum            'C24 H19 N O2'
_chemical_formula_weight         353.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-09-04
_audit_creation_method           'by CrystalStructure 4.1'
_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                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   7.6334(16)
_cell_length_b                   14.828(3)
_cell_length_c                   15.793(3)
_cell_measurement_reflns_used    2113
_cell_measurement_temperature    125
_cell_measurement_theta_max      75.60
_cell_measurement_theta_min      25.70
_cell_volume                     1787.6(6)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      125
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0868
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10230
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.249
_diffrn_reflns_theta_min         4.090
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744.00
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.32
_refine_ls_abs_structure_details
;
 Flack x determined using 1158 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, S., Flack, H.D. and Wagner, T. Acta Cryst. B69 (2013) 249-259.).
;
_refine_ls_abs_structure_Flack   -0.08(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3125
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0499
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0613P)^2^+0.2300P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1250
_reflns_number_gt                3049
_reflns_number_total             3125
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c8ob01795f3.cif
_cod_data_source_block           +16
_cod_depositor_comments
'Adding full bibliography for 7156430--7156433.cif.'
_cod_database_code               7156433
_shelx_res_checksum              13607