Phosphoric Acid-Catalyzed Formation of Hydrogen-Bonded ortho-Quinone Methides. Enantioselective Cycloaddition with β-Dicarbonyl Compounds toward Benzannulated Oxygen Heterocycles.
Göricke, Fabian; Haseloff, Stefan; Laue, Michael; Schneider, Maximilian; Brumme, Thomas; Schneider, Christoph; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01375

data_4038716
_publ_section_title
;
 Phosphoric Acid-Catalyzed Formation of Hydrogen-Bonded ortho-Quinone
 Methides. Enantioselective Cycloaddition with \b-Dicarbonyl Compounds
 toward Benzannulated Oxygen Heterocycles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01375
_journal_year                    2020
_chemical_formula_sum            'C21 H19 O2'
_chemical_formula_weight         303.36
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.72090(10)
_cell_length_b                   8.72090(10)
_cell_length_c                   41.8621(6)
_cell_measurement_reflns_used    894
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      6
_cell_volume                     3183.78(7)
_computing_cell_refinement       'PILATUS (Fa.STOE)'
_computing_data_collection       'PILATUS (Fa.STOE)'
_computing_data_reduction        'PILATUS (Fa.STOE)'
_computing_molecular_graphics    'ORTEP3 for WINDOWS (L.J.Farrugia)'
_computing_publication_material  'WINGX (L.J.Farrugia)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'STADIVARI (Fa.STOE)'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0086
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            37385
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         70.626
_diffrn_reflns_theta_min         4.224
_diffrn_source                   'sealed tube Cu'
_exptl_absorpt_coefficient_mu    0.079
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.158
_exptl_crystal_description       none
_exptl_crystal_F_000             161
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1115 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.115
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.0984
_reflns_Friedel_coverage         0.609
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2967
_reflns_number_total             3050
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01375_si_008.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        3183.78(9)
_cod_database_code               4038716
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              64865
_shelx_hkl_checksum              22628