Hydroxypyridinones with enhanced iron chelating properties. Synthesis, characterization and in vivo tests of 5-hydroxy-2-(hydroxymethyl)pyridine-4(1H)-one.
Lachowicz, J. I.; Nurchi, V. M.; Crisponi, G.; Jaraquemada-Pelaez, M G; Arca, M.; Pintus, A.; Santos, M. A.; Quintanova, C.; Gano, L.; Szewczuk, Z.; Zoroddu, M. A.; Peana, M.; Domínguez-Martín, A; Choquesillo-Lazarte, D; Dalton transactions (Cambridge, England : 2003) 45 (2016) 6517–6528; doi:10.1039/c6dt00129g

data_7038537
_publ_section_title
;
 Hydroxypyridinones with enhanced iron chelating properties. Synthesis,
 characterization and in vivo tests of
 5-hydroxy-2-(hydroxymethyl)pyridine-4(1H)-one.
;
_journal_issue                   15
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6517
_journal_page_last               6528
_journal_paper_doi               10.1039/c6dt00129g
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C6 H7 N O3'
_chemical_formula_sum            'C6 H7 N O3'
_chemical_formula_weight         141.13
_chemical_name_common            5-hydroxy-2-hydroxymethylpyridin-4(1H)-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-03-25 deposited with the CCDC.
2016-02-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8410(4)
_cell_length_b                   7.0291(3)
_cell_length_c                   12.6402(4)
_cell_measurement_reflns_used    3530
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.480
_cell_measurement_theta_min      3.317
_cell_volume                     607.82(5)
_computing_cell_refinement       'Bruker Apex2, 2014'
_computing_data_collection       'Bruker Apex2, 2014'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8040
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         3.223
_diffrn_source                   'high brilliance microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 532 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.5(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0264
_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^)+(0.0324P)^2^+0.1750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0666
_refine_ls_wR_factor_ref         0.0675
_reflns_Friedel_coverage         0.667
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                1346
_reflns_number_total             1390
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6dt00129g2.cif
_cod_data_source_block           15jnac842
_cod_depositor_comments          'Adding full bibliography for 7038537.cif.'
_cod_database_code               7038537
_shelx_estimated_absorpt_t_min   0.988
_shelx_estimated_absorpt_t_max   0.988
_shelxl_version_number           2013-3
_shelx_res_checksum              42328