One-pot Synthesis of 1-Hydroxyacridones from para-Quinols and ortho-Methoxycarbonylaryl Isocyanates.
Wu, Jing; Zhang, Jinzhu; Soto-Acosta, Ruben; Mao, Lili; Lian, Jiahui; Chen, Kenny; Pillon, Guy; Zhang, Guoqi; Geraghty, Robert J.; Zheng, Shengping; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03307

data_4037981
_publ_section_title
;
 One-pot Synthesis of 1-Hydroxyacridones from para-Quinols and
 ortho-Methoxycarbonylaryl Isocyanates.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03307
_journal_year                    2020
_chemical_formula_moiety         'C15 H11 N O4'
_chemical_formula_sum            'C15 H11 N O4'
_chemical_formula_weight         269.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.2090(17)
_cell_length_b                   6.6997(10)
_cell_length_c                   29.003(4)
_cell_measurement_reflns_used    9652
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      33.03
_cell_measurement_theta_min      2.81
_cell_volume                     2372.3(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            65989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         31.502
_diffrn_reflns_theta_min         2.809
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.6479
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3940
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0767
_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^)+(0.1300P)^2^+3.9099P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2476
_refine_ls_wR_factor_ref         0.2514
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3624
_reflns_number_total             3940
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03307_si_003.cif
_cod_data_source_block           me_enol
_cod_original_cell_volume        2372.4(6)
_cod_database_code               4037981
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.929
_shelx_estimated_absorpt_t_max   0.971
_shelx_res_checksum              27397
_shelx_hkl_checksum              75875