Synthesis of 3-Hydroxy-4-arylquinolin-2-ones Including Viridicatol via a Darzens Condensation/Friedel-Crafts Alkylation Strategy.
Mamedov, Vakhid A.; Mamedova, Vera L.; Kadyrova, Saniya F.; Galimullina, Venera R.; Khikmatova, Gul'naz Z.; Korshin, Dmitry E.; Gubaidullin, Aidar T.; Krivolapov, Dmitry B.; Rizvanov, Il'dar Kh; Bazanova, Olga B.; Sinyashin, Oleg G.; Latypov, Shamil K.; The Journal of organic chemistry 83 (2018) 13132–13145; doi:10.1021/acs.joc.8b01871

data_4035738
_publ_section_title
;
 Synthesis of 3-Hydroxy-4-arylquinolin-2-ones Including Viridicatol via a
 Darzens Condensation/Friedel-Crafts Alkylation Strategy.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13132
_journal_page_last               13145
_journal_paper_doi               10.1021/acs.joc.8b01871
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C16 H13 Br Cl N O2'
_chemical_formula_sum            'C16 H13 Br Cl N O2'
_chemical_formula_weight         366.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.045(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7083(11)
_cell_length_b                   12.3985(9)
_cell_length_c                   9.9543(9)
_cell_measurement_reflns_used    2010
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.48
_cell_measurement_theta_min      2.79
_cell_volume                     1625.9(2)
_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-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1073
_diffrn_reflns_av_unetI/netI     0.1827
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20243
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.764
_diffrn_reflns_theta_min         3.093
_exptl_absorpt_coefficient_mu    2.695
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.4824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 G.M. Sheldrick (1998a). SADABS v.2.01, Bruker.
 Siemens Area Detector Absorption Correction Program.
 Bruker AXS. Madison. Wisconsin. USA
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.824
_exptl_crystal_size_mid          0.723
_exptl_crystal_size_min          0.194
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.888
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         6348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.888
_refine_ls_R_factor_all          0.2673
_refine_ls_R_factor_gt           0.0573
_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^)+(0.0734P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1860
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1743
_reflns_number_total             6348
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01871_si_008.cif
_cod_data_source_block           vakh_viri8
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035738
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.215
_shelx_estimated_absorpt_t_max   0.623
_exptl_absorpt_special_details
;
 Additional spherical absorption correction applied with mu*r =  0.2000
 Lambda/2 correction factor = 0.0015
;
_shelx_res_checksum              52619
_shelx_hkl_checksum              13151