Conjugate Addition of Carbon Acids to β,γ-Unsaturated α-Keto Esters: Product Tautomerism and Applications for Asymmetric Synthesis of Benzo[<i>a</i>]phenazin-5-ol Derivatives.
Tukhvatshin, Rinat S.; Kucherenko, Alexander S.; Nelyubina, Yulia V.; Zlotin, Sergei G.; The Journal of organic chemistry 84 (2019) 13824–13831; doi:10.1021/acs.joc.9b02021

data_4034556
_publ_section_title
;
 Conjugate Addition of Carbon Acids to \b,\g-Unsaturated \a-Keto Esters:
 Product Tautomerism and Applications for Asymmetric Synthesis of
 Benzo[<i>a</i>]phenazin-5-ol Derivatives.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13824
_journal_page_last               13831
_journal_paper_doi               10.1021/acs.joc.9b02021
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H18 O6'
_chemical_formula_sum            'C21 H18 O6'
_chemical_formula_weight         366.35
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2943(4)
_cell_length_b                   10.1497(4)
_cell_length_c                   19.3054(7)
_cell_measurement_reflns_used    2666
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_cell_volume                     1821.16(13)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'APEX2 (Bruker, 2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX2 DUO CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13301
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.500
_diffrn_reflns_theta_min         4.923
_exptl_absorpt_coefficient_mu    0.818
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1335 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0267
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.1341P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0708
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                3150
_reflns_number_total             3223
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02021_si_001.cif
_cod_data_source_block           1
_cod_database_code               4034556
_shelx_estimated_absorpt_t_min   0.763
_shelx_estimated_absorpt_t_max   0.992
_shelxl_version_number           2014/6
_shelx_res_checksum              22107
_shelx_hkl_checksum              74185