Quinolone-Hydroxyquinoline Tautomerism in Quinolone 3-Esters. Preserving the 4-Oxoquinoline Structure To Retain Antimalarial Activity.
Horta, Pedro; Kuş, Nihal; Henriques, Marta Sofia C.; Paixão, José A; Coelho, Lis; Nogueira, Fátima; O'Neill, Paul M; Fausto, Rui; Cristiano, Maria Lurdes Santos; The Journal of organic chemistry 80 (2015) 12244–12257; doi:10.1021/acs.joc.5b02169

data_4036475
_publ_section_title
;
 Quinolone-Hydroxyquinoline Tautomerism in Quinolone 3-Esters. Preserving
 the 4-Oxoquinoline Structure To Retain Antimalarial Activity.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12244
_journal_page_last               12257
_journal_paper_doi               10.1021/acs.joc.5b02169
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C13 H14 Cl N O3'
_chemical_formula_sum            'C13 H14 Cl N O3'
_chemical_formula_weight         267.70
_chemical_melting_point          420
_chemical_name_systematic
;
Ethyl 4-hydroxy-5-methyl quinolinium chloride 3-carboxylate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                76.882(2)
_cell_angle_beta                 77.792(3)
_cell_angle_gamma                71.232(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2031(5)
_cell_length_b                   9.4082(5)
_cell_length_c                   10.7921(7)
_cell_measurement_reflns_used    2380
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.772
_cell_measurement_theta_min      6.475
_cell_volume                     666.76(7)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector diffractometer'
_diffrn_measurement_method       '\f and \w'
_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  0.0388
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13439
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.476
_diffrn_reflns_theta_min         3.021
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2000)'
_exptl_crystal_colour            'light orange'
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       needle
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   0.977
_exptl_transmission_factor_min   0.973
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3271
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1271
_refine_ls_R_factor_gt           0.0559
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0753P)^2^+0.0688P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1377
_refine_ls_wR_factor_ref         0.1661
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1653
_reflns_number_total             3271
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02169_si_002.cif
_cod_data_source_block           crist
_cod_database_code               4036475
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.912
_shelx_estimated_absorpt_t_max   0.977
_shelx_res_checksum              50007
_shelx_hkl_checksum              84150