#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/82/2018201.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_2018201
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                   24.9344(4)
_cell_length_b                   24.9344(4)
_cell_length_c                   5.24150(10)
_cell_measurement_reflns_used    8747
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      68.37
_cell_measurement_theta_min      3.55
_cell_volume                     2822.18(8)
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'APEX2 (Bruker, 2006)'
_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 5.6
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8 Proteum'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  'graded multilayer optics'
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            14184
_diffrn_reflns_theta_full        68.36
_diffrn_reflns_theta_max         68.36
_diffrn_reflns_theta_min         3.55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.845
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1188
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.157
_refine_ls_extinction_coef       0.00050(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         1161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0657P)²+2.7780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1129
_reflns_number_gt                1077
_reflns_number_total             1161
_reflns_threshold_expression     I>2σ(I)
_iucr_refine_instructions_details
;
TITL x09060 in R-3
CELL 1.54178  24.9344  24.9344   5.2415  90.000  90.000 120.000
ZERR   18.00   0.0004   0.0004   0.0001   0.000   0.000   0.000
LATT  3
SYMM -Y, X-Y, Z
SYMM -X+Y, -X, Z
SFAC C H N O
UNIT 108 126 18 36
TEMP -183.000
SIZE 0.15 0.02 0.02
L.S. 6
BOND $H
CONF
HTAB
EQIV $1 -x+1, -y+1, -z
EQIV $2 -y+4/3, x-y+2/3, z+2/3
HTAB N1 O1_$1
HTAB O2 O1_$2
MPLA N1 c2 c3 c4 c5 c6 o1 o2 c7
RTAB tors c4 c5 o2 h2
ACTA
REM The solvent in this one was water. The largest difference map features
REM were in the middle of the solvent channels, but there is insufficient
REM electron density to make any sort of a sensible model.  Use of SQUEEZE
REM in Platon 'removes' 19 electrons from the void.  It seems safe to assume
REM that the channels can be at least partly de-populated of solvent without
REM the crystals completely collapsing.
FMAP 2
PLAN 5
WGHT    0.065700    2.778000
EXTI    0.000495
FVAR       0.37248
N1    3    0.554160    0.508687    0.254822    11.00000    0.02129    0.01974 =
         0.01951   -0.00099   -0.00056    0.00725
AFIX  43
H1    2    0.533775    0.484352    0.125949    11.00000   -1.20000
AFIX   0
C2    1    0.550013    0.560817    0.286156    11.00000    0.01915    0.02024 =
         0.02046    0.00252    0.00402    0.00744
C3    1    0.583405    0.598805    0.496481    11.00000    0.02214    0.02023 =
         0.02214    0.00013    0.00353    0.00828
AFIX  43
H3    2    0.582497    0.635805    0.529512    11.00000   -1.20000
AFIX   0
C4    1    0.616782    0.582327    0.651224    11.00000    0.02112    0.02265 =
         0.01923   -0.00083    0.00155    0.00645
AFIX  43
H4    2    0.638506    0.608058    0.792068    11.00000   -1.20000
AFIX   0
C5    1    0.619913    0.528250    0.607923    11.00000    0.02045    0.02288 =
         0.02121    0.00428    0.00235    0.00826
C6    1    0.587232    0.490970    0.406238    11.00000    0.01985    0.02120 =
         0.02262    0.00313    0.00332    0.00772
O1    4    0.517313    0.571825    0.131725    11.00000    0.02420    0.02223 =
         0.02247    0.00014   -0.00150    0.01050
O2    4    0.652116    0.510981    0.766085    11.00000    0.02468    0.02540 =
         0.02779    0.00232   -0.00430    0.00979
AFIX 147
H2    2    0.687440    0.541523    0.793470    11.00000   -1.50000
AFIX   0
C7    1    0.583575    0.430913    0.343879    11.00000    0.02900    0.02311 =
         0.03166   -0.00146   -0.00302    0.01212
AFIX 137
H7A   2    0.613283    0.425938    0.449144    11.00000   -1.50000
H7B   2    0.593425    0.430479    0.163156    11.00000   -1.50000
H7C   2    0.541613    0.396830    0.378331    11.00000   -1.50000
HKLF 4
REM  x09060 in R-3
REM R1 =  0.0373 for   1077 Fo > 4sig(Fo)  and  0.0398 for all   1161 data
REM     85 parameters refined using      0 restraints
END
WGHT      0.0657      2.7784
REM Highest difference peak  0.359,  deepest hole -0.157,  1-sigma level  0.051
Q1    1   0.6667  0.3333  0.4614  10.33333  0.05    0.36
Q2    1   0.6667  0.3333  0.7384  10.33333  0.05    0.31
Q3    1   0.6222  0.5574  0.6029  11.00000  0.05    0.20
Q4    1   0.5948  0.5058  0.5405  11.00000  0.05    0.16
Q5    1   0.5468  0.4041  0.2259  11.00000  0.05    0.15
;
_cod_data_source_file            mx3051.cif
_cod_data_source_block           Id
_cod_original_cell_volume        2822.17(8)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               2018201
_cod_database_fobs_code          2018201
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(5) 0.50869(5) 0.2548(2) 0.0215(3) Uani d . 1 1
H H1 0.5338 0.4844 0.1259 0.026 Uiso calc R 1 1
C C2 0.55001(6) 0.56082(6) 0.2862(2) 0.0210(3) Uani d . 1 1
C C3 0.58341(6) 0.59881(6) 0.4965(2) 0.0225(3) Uani d . 1 1
H H3 0.5825 0.6358 0.5295 0.027 Uiso calc R 1 1
C C4 0.61678(6) 0.58233(6) 0.6512(2) 0.0230(3) Uani d . 1 1
H H4 0.6385 0.6081 0.7921 0.028 Uiso calc R 1 1
C C5 0.61991(6) 0.52825(6) 0.6079(2) 0.0227(3) Uani d . 1 1
C C6 0.58723(6) 0.49097(6) 0.4062(2) 0.0224(3) Uani d . 1 1
O O1 0.51731(4) 0.57183(4) 0.13173(16) 0.0235(3) Uani d . 1 1
O O2 0.65212(4) 0.51098(4) 0.76609(18) 0.0272(3) Uani d . 1 1
H H2 0.6874 0.5415 0.7935 0.041 Uiso calc R 1 1
C C7 0.58358(7) 0.43091(6) 0.3439(3) 0.0283(4) Uani d . 1 1
H H7A 0.6133 0.4259 0.4491 0.042 Uiso calc R 1 1
H H7B 0.5934 0.4305 0.1632 0.042 Uiso calc R 1 1
H H7C 0.5416 0.3968 0.3783 0.042 Uiso calc R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0213(6) 0.0197(6) 0.0195(5) 0.0073(4) -0.0006(4) -0.0010(4)
C2 0.0192(6) 0.0202(6) 0.0205(6) 0.0074(5) 0.0040(5) 0.0025(5)
C3 0.0221(6) 0.0202(6) 0.0221(6) 0.0083(5) 0.0035(5) 0.0001(5)
C4 0.0211(6) 0.0226(7) 0.0192(6) 0.0065(5) 0.0015(5) -0.0008(5)
C5 0.0205(6) 0.0229(7) 0.0212(6) 0.0083(5) 0.0024(5) 0.0043(5)
C6 0.0198(6) 0.0212(7) 0.0226(6) 0.0077(5) 0.0033(5) 0.0031(5)
O1 0.0242(5) 0.0222(5) 0.0225(5) 0.0105(4) -0.0015(3) 0.0001(3)
O2 0.0247(5) 0.0254(5) 0.0278(5) 0.0098(4) -0.0043(4) 0.0023(4)
C7 0.0290(7) 0.0231(7) 0.0317(7) 0.0121(6) -0.0030(5) -0.0015(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 125.68(11)
C2 N1 H1 117.2
C6 N1 H1 117.2
O1 C2 N1 119.40(11)
O1 C2 C3 125.11(12)
N1 C2 C3 115.49(11)
C4 C3 C2 120.20(12)
C4 C3 H3 119.9
C2 C3 H3 119.9
C3 C4 C5 121.81(12)
C3 C4 H4 119.1
C5 C4 H4 119.1
O2 C5 C6 119.82(12)
O2 C5 C4 121.83(12)
C6 C5 C4 118.29(12)
N1 C6 C5 118.52(12)
N1 C6 C7 116.97(11)
C5 C6 C7 124.48(12)
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 1.3644(17)
N1 C6 1.3673(17)
N1 H1 0.8800
C2 O1 1.2725(15)
C2 C3 1.4203(17)
C3 C4 1.3643(19)
C3 H3 0.9500
C4 C5 1.4075(19)
C4 H4 0.9500
C5 O2 1.3650(16)
C5 C6 1.3741(19)
C6 C7 1.4903(19)
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 2.7809(14) 174.4 no
O2 H2 O1 8_655 0.84 1.81 2.6366(13) 169.8 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 -179.71(11)
C6 N1 C2 C3 -0.15(18)
O1 C2 C3 C4 179.59(12)
N1 C2 C3 C4 0.07(17)
C2 C3 C4 C5 0.63(19)
C3 C4 C5 O2 -178.45(11)
C3 C4 C5 C6 -1.24(19)
C2 N1 C6 C5 -0.46(19)
C2 N1 C6 C7 177.76(11)
O2 C5 C6 N1 178.39(10)
C4 C5 C6 N1 1.12(18)
O2 C5 C6 C7 0.31(19)
C4 C5 C6 C7 -176.95(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 23979851
