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_4035740
_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 H14 Cl N O2'
_chemical_formula_sum            'C16 H14 Cl N O2'
_chemical_formula_weight         287.73
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 108.320(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1146(16)
_cell_length_b                   12.3208(18)
_cell_length_c                   10.0165(11)
_cell_measurement_reflns_used    1786
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.06
_cell_measurement_theta_min      3.31
_cell_volume                     1419.3(3)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.968
_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  0.0798
_diffrn_reflns_av_unetI/netI     0.0848
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13329
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.002
_diffrn_reflns_theta_min         3.585
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6767
_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    1.347
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.611
_exptl_crystal_size_mid          0.298
_exptl_crystal_size_min          0.208
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3314
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0342P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0970
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2206
_reflns_number_total             3314
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01871_si_009.cif
_cod_data_source_block           vakh619
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035740
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.832
_shelx_estimated_absorpt_t_max   0.946
_exptl_absorpt_special_details
;
 Additional spherical absorption correction applied with mu*r =  0.2000
 Lambda/2 correction factor = 0.0015
;
_shelx_res_checksum              87894
_shelx_hkl_checksum              49022