#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/86/2238639.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2238639
loop_
_publ_author_name
'Reyes, Héctor'
'Aguirre, Gerardo'
'Chávez, Daniel'
_publ_section_title
;
 4-Hydroxy-6-methylpyridin-2(1H)-one
;
_journal_coeditor_code           IM2437
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1534
_journal_paper_doi               10.1107/S1600536813024240
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C6 H7 N O2'
_chemical_formula_moiety         'C6 H7 N O2'
_chemical_formula_sum            'C6 H7 N O2'
_chemical_formula_weight         125.13
_chemical_name_systematic
;
4-Hydroxy-6-methylpyridin-2(1H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.303(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.7082(5)
_cell_length_b                   12.2988(8)
_cell_length_c                   10.0418(7)
_cell_measurement_reflns_used    51
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12.29
_cell_measurement_theta_min      6.62
_cell_volume                     581.32(8)
_computing_cell_refinement       'XSCANS (Siemens, 1996)'
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'XSCANS (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '2θ/ω 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  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2445
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.62
_diffrn_standards_decay_%        9.41
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.2589
_exptl_absorpt_correction_T_min  0.2162
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XSCANS; Siemens, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             264
_exptl_crystal_size_max          .65
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .18
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.248
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0502
_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/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1602
_reflns_number_gt                1269
_reflns_number_total             1701
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            im2437.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2238639
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.7844(3) 0.91089(9) 0.60053(9) 0.0364(3) Uani d . 1 1
O O2 0.2045(2) 0.68616(10) 0.32761(10) 0.0396(3) Uani d . 1 1
H H2B 0.2292 0.6556 0.2562 0.059 Uiso calc R 1 1
N N1 0.7786(3) 0.93124(10) 0.37596(11) 0.0301(3) Uani d . 1 1
H H1A 0.9049 0.9813 0.3858 0.036 Uiso calc R 1 1
C C1 0.6811(3) 0.88072(12) 0.48782(12) 0.0288(3) Uani d . 1 1
C C2 0.4786(3) 0.79830(13) 0.46911(13) 0.0326(3) Uani d . 1 1
H H2A 0.4026 0.7638 0.5426 0.039 Uiso calc R 1 1
C C3 0.3912(3) 0.76793(12) 0.34229(13) 0.0303(3) Uani d . 1 1
C C4 0.4958(3) 0.82420(12) 0.23072(14) 0.0321(3) Uani d . 1 1
H H4A 0.4353 0.8053 0.1450 0.038 Uiso calc R 1 1
C C5 0.6858(3) 0.90624(12) 0.25012(13) 0.0293(3) Uani d . 1 1
C C6 0.8049(4) 0.97389(15) 0.14088(15) 0.0403(4) Uani d . 1 1
H H6D 0.7267 0.9501 0.0567 0.060 Uiso calc R 1 1
H H6A 1.0078 0.9662 0.1411 0.060 Uiso calc R 1 1
H H6B 0.7566 1.0488 0.1548 0.060 Uiso calc R 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 O2 H2B 109.5
C5 N1 C1 123.42(13)
C5 N1 H1A 118.3
C1 N1 H1A 118.3
O1 C1 N1 117.79(14)
O1 C1 C2 124.99(13)
N1 C1 C2 117.21(12)
C3 C2 C1 120.46(13)
C3 C2 H2A 119.8
C1 C2 H2A 119.8
O2 C3 C2 119.01(13)
O2 C3 C4 121.24(12)
C2 C3 C4 119.74(14)
C5 C4 C3 119.30(13)
C5 C4 H4A 120.4
C3 C4 H4A 120.4
C4 C5 N1 119.76(13)
C4 C5 C6 124.34(13)
N1 C5 C6 115.90(14)
C5 C6 H6D 109.5
C5 C6 H6A 109.5
H6D C6 H6A 109.5
C5 C6 H6B 109.5
H6D C6 H6B 109.5
H6A C6 H6B 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2768(16)
O2 C3 1.3418(18)
O2 H2B 0.8200
N1 C5 1.3629(17)
N1 C1 1.3719(17)
N1 H1A 0.8600
C1 C2 1.401(2)
C2 C3 1.3809(19)
C2 H2A 0.9300
C3 C4 1.415(2)
C4 C5 1.359(2)
C4 H4A 0.9300
C5 C6 1.496(2)
C6 H6D 0.9600
C6 H6A 0.9600
C6 H6B 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A O1 3_776 0.86 1.98 2.835(2) 175.4
O2 H2B O1 4_575 0.82 1.79 2.609(2) 179.8
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C5 N1 C1 O1 179.84(14)
C5 N1 C1 C2 1.0(2)
O1 C1 C2 C3 -176.62(15)
N1 C1 C2 C3 2.2(2)
C1 C2 C3 O2 177.69(13)
C1 C2 C3 C4 -3.3(2)
O2 C3 C4 C5 -179.71(13)
C2 C3 C4 C5 1.3(2)
C3 C4 C5 N1 1.8(2)
C3 C4 C5 C6 -178.05(15)
C1 N1 C5 C4 -3.0(2)
C1 N1 C5 C6 176.88(14)
