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_4038718
_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
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_chemical_formula_sum            'C19 H18 O3'
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_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
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_cell_measurement_reflns_used    4267
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_cell_volume                     1506.42(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics
;
 ORTEP3 for Windows
 L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
 or
 DIAMOND Version 4.5.3
 K. Brandenburg, Crystal Impact GbR, Bonn, Germany
;
_computing_publication_material
;
 WINGX
 L.J. Farrugia,
 J. Appl. Cryst., 2012, 45, 849-854.
;
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_diffrn_ambient_temperature      130(2)
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_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15011
_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_full        30.510
_diffrn_reflns_theta_max         32.592
_diffrn_reflns_theta_min         2.305
_diffrn_source                   'fine-focus sealed X-ray tube'
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_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71268
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_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1411 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(6)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0503P)^2^+0.0755P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1084
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.885
_reflns_number_gt                4205
_reflns_number_total             5031
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01375_si_004.cif
_cod_data_source_block           x3206fin
_cod_database_code               4038718
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              66377
_shelx_hkl_checksum              75209