#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/84/2218498.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_2218498
loop_
_publ_author_name
'Dong, Cheng-Ming'
'Pu, Shou-Cheng'
'Gao, Wen-Yuan'
_publ_section_title
;
 3,5-Dihydroxy-2-methyl-4H-pyran-4-one
;
_journal_coeditor_code           PV2074
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1032
_journal_paper_doi               10.1107/S1600536808010957
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C6 H6 O4'
_chemical_formula_moiety         'C6 H6 O4'
_chemical_formula_sum            'C6 H6 O4'
_chemical_formula_weight         142.11
_chemical_name_systematic
;
3,5-Dihydroxy-2-methyl-4H-pyran-4-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                 92.77(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9400(14)
_cell_length_b                   6.0648(12)
_cell_length_c                   14.008(3)
_cell_measurement_reflns_used    1620
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.861
_cell_measurement_theta_min      1.455
_cell_volume                     588.9(2)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_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      113(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3970
_diffrn_reflns_theta_full        27.85
_diffrn_reflns_theta_max         27.85
_diffrn_reflns_theta_min         2.91
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_correction_T_min  0.9810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1381
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0318
_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)+(0.0654P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0963
_reflns_number_gt                1166
_reflns_number_total             1381
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2074.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      ' P 21/n'
_cod_database_code               2218498
_cod_database_fobs_code          2218498
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_occupancy
O O3 0.27997(10) 1.01120(11) 0.27250(5) 0.0149(2) Uani d 1
O O1 0.76427(10) 1.05517(12) 0.44524(5) 0.0157(2) Uani d 1
O O4 0.56909(12) 0.69576(12) 0.26153(5) 0.0171(2) Uani d 1
O O2 0.32648(11) 1.36372(12) 0.40092(5) 0.0173(2) Uani d 1
C C4 0.43152(15) 1.02588(15) 0.32615(7) 0.0124(2) Uani d 1
C C5 0.46324(15) 1.20540(16) 0.39217(7) 0.0132(2) Uani d 1
C C3 0.58183(15) 0.86536(16) 0.32479(7) 0.0127(2) Uani d 1
C C2 0.74196(15) 0.88197(16) 0.38483(7) 0.0139(2) Uani d 1
C C6 0.62774(16) 1.21333(17) 0.44749(7) 0.0157(2) Uani d 1
C C1 0.90601(15) 0.72547(19) 0.39113(8) 0.0174(3) Uani d 1
H H4 0.656(2) 1.323(2) 0.4929(10) 0.021(3) Uiso d 1
H H3 0.871(2) 0.582(2) 0.3585(10) 0.028(3) Uiso d 1
H H1 1.017(2) 0.782(2) 0.3616(11) 0.037(4) Uiso d 1
H H2 0.940(2) 0.689(2) 0.4591(10) 0.025(3) Uiso d 1
H H5 0.271(3) 1.393(3) 0.3397(14) 0.054(5) Uiso d 1
H H6 0.454(3) 0.669(2) 0.2453(11) 0.037(4) Uiso d 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
O3 0.0141(4) 0.0150(4) 0.0153(4) 0.0004(3) -0.0022(3) -0.0013(3)
O1 0.0155(4) 0.0165(4) 0.0148(4) -0.0005(3) -0.0020(3) -0.0020(3)
O4 0.0136(4) 0.0163(4) 0.0211(4) 0.0004(3) -0.0008(3) -0.0080(3)
O2 0.0233(4) 0.0142(4) 0.0142(4) 0.0058(3) -0.0018(3) -0.0018(3)
C4 0.0142(5) 0.0125(5) 0.0105(4) -0.0022(4) 0.0016(4) 0.0017(3)
C5 0.0177(5) 0.0106(5) 0.0116(4) 0.0007(4) 0.0021(4) 0.0008(3)
C3 0.0138(5) 0.0118(5) 0.0128(5) -0.0019(4) 0.0023(4) -0.0011(3)
C2 0.0145(5) 0.0141(5) 0.0132(4) -0.0017(4) 0.0024(4) -0.0003(3)
C6 0.0200(6) 0.0133(5) 0.0139(5) -0.0012(4) 0.0006(4) -0.0020(4)
C1 0.0126(5) 0.0200(6) 0.0195(5) 0.0013(4) 0.0001(4) -0.0010(4)
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'
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
C6 O1 C2 120.47(8)
C3 O4 H6 110.7(11)
C5 O2 H5 107.9(12)
O3 C4 C3 122.06(9)
O3 C4 C5 122.13(9)
C3 C4 C5 115.82(9)
C6 C5 O2 119.86(9)
C6 C5 C4 119.68(10)
O2 C5 C4 120.44(9)
O4 C3 C2 118.92(9)
O4 C3 C4 120.04(9)
C2 C3 C4 121.01(9)
O1 C2 C3 120.53(9)
O1 C2 C1 113.31(9)
C3 C2 C1 126.15(9)
C5 C6 O1 122.45(9)
C5 C6 H4 124.0(8)
O1 C6 H4 113.5(8)
C2 C1 H3 111.1(8)
C2 C1 H1 112.2(9)
H3 C1 H1 107.1(13)
C2 C1 H2 110.3(8)
H3 C1 H2 106.4(12)
H1 C1 H2 109.5(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C4 1.2659(13)
O1 C6 1.3497(13)
O1 C2 1.3531(12)
O4 C3 1.3577(12)
O4 H6 0.838(18)
O2 C5 1.3598(12)
O2 H5 0.94(2)
C4 C3 1.4276(14)
C4 C5 1.4386(13)
C5 C6 1.3494(16)
C3 C2 1.3646(15)
C2 C1 1.4816(15)
C6 H4 0.936(14)
C1 H3 1.005(15)
C1 H1 0.956(17)
C1 H2 0.996(15)
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
O4 H6 O3 2_545 0.838(18) 1.89(2) 2.6902(12) 159.6(13)
O2 H5 O3 2 0.94(2) 1.75(2) 2.6596(12) 162.6(17)
O4 H6 O3 . 0.838(18) 2.44(2) 2.7820(12) 105.4(10)
C1 H3 O4 . 1.005(15) 2.537(14) 2.8957(15) 100.5(9)
C6 H4 O2 3_686 0.936(14) 2.412(13) 3.3354(14) 169.4(12)
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
O3 C4 C5 C6 -179.79(9)
C3 C4 C5 C6 0.12(14)
O3 C4 C5 O2 1.94(15)
C3 C4 C5 O2 -178.15(8)
O3 C4 C3 O4 3.12(15)
C5 C4 C3 O4 -176.78(8)
O3 C4 C3 C2 -178.50(9)
C5 C4 C3 C2 1.59(14)
C6 O1 C2 C3 0.47(15)
C6 O1 C2 C1 179.47(9)
O4 C3 C2 O1 176.47(9)
C4 C3 C2 O1 -1.93(15)
O4 C3 C2 C1 -2.39(16)
C4 C3 C2 C1 179.21(9)
O2 C5 C6 O1 176.71(9)
C4 C5 C6 O1 -1.58(15)
C2 O1 C6 C5 1.32(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 63795
