Structural assignment of the enol–keto tautomers of one-pot synthesized 4-hydroxyquinolines/4-quinolones
Kang, On-Yu; Park, Seong Jun; Ahn, Hyojung; Jeong, Kyung Chae; Lim, Hwan Jung; Organic Chemistry Frontiers 6 (2019) 183–; doi:10.1039/C8QO00884A

data_1554437
_publ_section_title
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 Structural assignment of the enol--keto tautomers of one-pot synthesized
 4-hydroxyquinolines/4-quinolones
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_journal_issue                   2
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              183
_journal_paper_doi               10.1039/C8QO00884A
_journal_volume                  6
_journal_year                    2019
_chemical_formula_sum            'C13 H13 N O4 S'
_chemical_formula_weight         279.30
_chemical_name_systematic
'Methyl 4-hydroxy-7-methoxy-2-(methylthio)quinoline-3-carboxylate'
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
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2018-04-18 deposited with the CCDC.
2018-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.2940(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.10090(10)
_cell_length_b                   17.5658(2)
_cell_length_c                   8.18620(10)
_cell_measurement_reflns_used    5040
_cell_measurement_temperature    296(1)
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      2.32
_cell_volume                     1273.61(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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(1)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3202
_diffrn_reflns_theta_full        28.44
_diffrn_reflns_theta_max         28.44
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.9792
_exptl_absorpt_correction_T_min  0.9299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            silver
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane, Methanol'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0748P)^2^+0.1717P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1368
_reflns_number_gt                2545
_reflns_number_total             3202
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8qo00884a2.cif
_cod_data_source_block           20161124
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
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_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1554437