#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/81/2018198.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_2018198
loop_
_publ_author_name
'Parkin, Sean R.'
'Behrman, Edward J.'
_publ_section_title
;
 Channel-forming solvate crystals and isostructural solvent-free powder
 of 5-hydroxy-6-methyl-2-pyridone
;
_journal_coeditor_code           MX3051
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o324
_journal_page_last               o328
_journal_paper_doi               10.1107/S0108270111026254
_journal_volume                  67
_journal_year                    2011
_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
;
5-hydroxy-6-methyl-2-pyridone
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   24.9131(11)
_cell_length_b                   24.9131(11)
_cell_length_c                   5.2462(3)
_cell_measurement_reflns_used    1434
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     2819.9(2)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and local procedures
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 9.1
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_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  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            7559
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.83
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1188
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.244
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         1434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0519
_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)+(0.0907P)²+1.2147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1562
_reflns_number_gt                958
_reflns_number_total             1434
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            mx3051.cif
_cod_data_source_block           Ic1
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               2018198
_cod_database_fobs_code          2018198
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
N N1 0.55416(7) 0.50846(7) 0.2548(3) 0.0204(4) Uani d . 1 1
H H1 0.5337 0.4840 0.1265 0.024 Uiso calc R 1 1
C C2 0.55001(8) 0.56070(8) 0.2857(3) 0.0202(4) Uani d . 1 1
C C3 0.58352(8) 0.59872(8) 0.4970(3) 0.0220(4) Uani d . 1 1
H H3 0.5826 0.6357 0.5303 0.026 Uiso calc R 1 1
C C4 0.61677(8) 0.58222(8) 0.6513(3) 0.0220(4) Uani d . 1 1
H H4 0.6385 0.6079 0.7921 0.026 Uiso calc R 1 1
C C5 0.61978(8) 0.52811(9) 0.6076(3) 0.0217(5) Uani d . 1 1
C C6 0.58743(8) 0.49090(8) 0.4061(3) 0.0210(4) Uani d . 1 1
O O1 0.51731(6) 0.57186(6) 0.1321(2) 0.0229(4) Uani d . 1 1
O O2 0.65202(6) 0.51054(6) 0.7664(3) 0.0276(4) Uani d . 1 1
H H2 0.6881 0.5405 0.7873 0.041 Uiso calc R 1 1
C C7 0.58352(10) 0.43069(9) 0.3441(4) 0.0281(5) Uani d . 1 1
H H7A 0.6115 0.4245 0.4561 0.042 Uiso calc R 1 1
H H7B 0.5956 0.4311 0.1661 0.042 Uiso calc R 1 1
H H7C 0.5409 0.3969 0.3694 0.042 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
C2 N1 C6 125.63(15)
C2 N1 H1 117.2
C6 N1 H1 117.2
O1 C2 N1 119.68(15)
O1 C2 C3 125.03(17)
N1 C2 C3 115.28(16)
C4 C3 C2 120.31(18)
C4 C3 H3 119.8
C2 C3 H3 119.8
C3 C4 C5 121.69(17)
C3 C4 H4 119.2
C5 C4 H4 119.2
C6 C5 O2 119.49(17)
C6 C5 C4 118.61(17)
O2 C5 C4 121.84(16)
N1 C6 C5 118.46(17)
N1 C6 C7 116.76(16)
C5 C6 C7 124.73(17)
C5 O2 H2 109.5
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.366(2)
N1 C6 1.368(2)
N1 H1 0.8800
C2 O1 1.271(2)
C2 C3 1.426(2)
C3 C4 1.360(3)
C3 H3 0.9500
C4 C5 1.406(3)
C4 H4 0.9500
C5 C6 1.371(3)
C5 O2 1.372(2)
C6 C7 1.490(3)
O2 H2 0.8400
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
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
_geom_hbond_publ_flag
N1 H1 O1 10_665 0.88 1.90 2.7805(19) 174.7 no
O2 H2 O1 8_655 0.84 1.81 2.6398(18) 170.3 no
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
C6 N1 C2 O1 -179.81(16)
C6 N1 C2 C3 -0.5(2)
O1 C2 C3 C4 179.45(16)
N1 C2 C3 C4 0.2(2)
C2 C3 C4 C5 0.6(3)
C3 C4 C5 C6 -1.0(3)
C3 C4 C5 O2 -178.37(16)
C2 N1 C6 C5 0.1(3)
C2 N1 C6 C7 177.63(16)
O2 C5 C6 N1 178.12(15)
C4 C5 C6 N1 0.7(3)
O2 C5 C6 C7 0.8(3)
C4 C5 C6 C7 -176.70(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 23979851
