##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic     3,5-dihydroxy-2-hydroxymethyl-4H-pyran-4-one
_chemical_name_common     '3-hydroxykojic acid'
_chemical_formula_moiety     'C6 H6 O5'
_chemical_formula_sum     'C6 H6 O5'
_chemical_formula_iupac     'C6 H6 O5'
_chemical_formula_weight     158.11
_chemical_melting_point     460
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.2045(9)
_cell_length_b     8.9704(10)
_cell_length_c     9.6826(10)
_cell_angle_alpha     93.026(2)
_cell_angle_beta     109.337(2)
_cell_angle_gamma     109.787(2)
_cell_volume     621.71(12)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1957
_cell_measurement_theta_min     4.911
_cell_measurement_theta_max     56.108
_cell_measurement_temperature     293(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.513
_exptl_crystal_size_mid     0.502
_exptl_crystal_size_min     0.385
_exptl_crystal_density_diffrn     1.689
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     328
_exptl_absorpt_coefficient_mu     0.151
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.914
_exptl_absorpt_correction_T_max     0.939
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3405
_diffrn_reflns_av_R_equivalents     0.0628
_diffrn_reflns_av_sigmaI/netI     0.0432
_diffrn_reflns_theta_min     2.27
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.981
_diffrn_measured_fraction_theta_full     0.981
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2387
_reflns_number_gt     2007
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0672
_refine_ls_R_factor_gt     0.0609
_refine_ls_wR_factor_gt     0.1745
_refine_ls_wR_factor_ref     0.1818
_refine_ls_goodness_of_fit_ref     1.075
_refine_ls_restrained_S_all     1.075
_refine_ls_number_reflns     2387
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1098P)²+0.1959P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.552
_refine_diff_density_min     -0.393
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART (Bruker, 2000) '
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT and SHELXTL (Bruker, 2000)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
'ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997)
and CAMERON (Watkin et al., 1993) '
;
_computing_publication_material     'SHELXTL (Bruker, 2000)'
loop_
    _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_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    O1 1.0093(2) 0.58572(19) 0.80116(18) 0.0395(4) Uani d . 1 . . O
    O2 1.4542(2) 0.5796(2) 0.83150(19) 0.0435(5) Uani d . 1 . . O
    H2 1.4774 0.5107 0.7914 0.065 Uiso calc R 1 . . H
    O3 1.2114(2) 0.33178(19) 0.59512(18) 0.0412(4) Uani d . 1 . . O
    O4 0.8319(2) 0.25457(19) 0.49931(17) 0.0397(4) Uani d . 1 . . O
    H4 0.8893 0.2114 0.4676 0.059 Uiso calc R 1 . . H
    O5 0.6403(2) 0.41613(19) 0.77607(18) 0.0401(4) Uani d . 1 . . O
    H5 0.6083 0.3199 0.7800 0.060 Uiso calc R 1 . . H
    O6 0.8723(2) 0.15192(19) 0.90459(18) 0.0397(4) Uani d . 1 . . O
    O7 1.3335(2) 0.1999(2) 0.9222(2) 0.0567(6) Uani d . 1 . . O
    H7 1.3832 0.2659 1.0002 0.085 Uiso calc R 1 . . H
    O8 1.1186(2) -0.0459(2) 0.68921(19) 0.0447(5) Uani d . 1 . . O
    O9 0.7316(2) -0.1598(2) 0.5973(2) 0.0497(5) Uani d . 1 . . O
    H9 0.7939 -0.1873 0.5579 0.075 Uiso calc R 1 . . H
    O10 0.5079(3) 0.0972(3) 0.7481(5) 0.1091(12) Uani d . 1 . . O
    H10 0.4037 0.0655 0.7523 0.164 Uiso calc R 1 . . H
    C1 1.1945(3) 0.6202(3) 0.8477(3) 0.0380(6) Uani d . 1 . . C
    H1 1.2744 0.7040 0.9278 0.046 Uiso calc R 1 . . H
    C2 1.2670(3) 0.5386(2) 0.7830(2) 0.0308(5) Uani d . 1 . . C
    C3 1.1486(3) 0.4085(2) 0.6583(2) 0.0286(5) Uani d . 1 . . C
    C4 0.9531(3) 0.3751(2) 0.6146(2) 0.0288(5) Uani d . 1 . . C
    C5 0.8897(3) 0.4626(3) 0.6857(2) 0.0323(5) Uani d . 1 . . C
    C6 0.6914(3) 0.4430(3) 0.6508(2) 0.0378(5) Uani d . 1 . . C
    H6A 0.6743 0.5393 0.6192 0.045 Uiso calc R 1 . . H
    H6B 0.6107 0.3527 0.5693 0.045 Uiso calc R 1 . . H
    C7 1.0597(3) 0.2074(3) 0.9482(2) 0.0388(6) Uani d . 1 . . C
    H7A 1.1312 0.2923 1.0288 0.047 Uiso calc R 1 . . H
    C8 1.1469(3) 0.1460(3) 0.8812(2) 0.0348(5) Uani d . 1 . . C
    C9 1.0438(3) 0.0151(2) 0.7552(2) 0.0317(5) Uani d . 1 . . C
    C10 0.8451(3) -0.0382(2) 0.7131(2) 0.0322(5) Uani d . 1 . . C
    C11 0.7673(3) 0.0297(3) 0.7863(3) 0.0357(5) Uani d . 1 . . C
    C12 0.5636(3) -0.0203(3) 0.7497(4) 0.0617(9) Uani d . 1 . . C
    H12A 0.4979 -0.0904 0.6527 0.074 Uiso calc R 1 . . H
    H12B 0.5305 -0.0825 0.8221 0.074 Uiso calc R 1 . . H
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
    O1 0.0219(8) 0.0429(9) 0.0421(9) 0.0069(6) 0.0067(7) -0.0144(7)
    O2 0.0190(8) 0.0454(10) 0.0487(10) 0.0056(7) 0.0027(7) -0.0218(7)
    O3 0.0270(8) 0.0439(9) 0.0407(9) 0.0092(7) 0.0061(7) -0.0167(7)
    O4 0.0217(8) 0.0407(9) 0.0378(9) 0.0029(6) 0.0006(6) -0.0155(7)
    O5 0.0266(8) 0.0422(9) 0.0482(9) 0.0090(7) 0.0152(7) -0.0007(7)
    O6 0.0229(8) 0.0383(9) 0.0458(9) 0.0047(6) 0.0081(7) -0.0137(7)
    O7 0.0188(8) 0.0720(13) 0.0519(11) 0.0001(8) 0.0033(7) -0.0296(9)
    O8 0.0258(8) 0.0430(9) 0.0520(10) 0.0045(7) 0.0110(7) -0.0169(8)
    O9 0.0222(8) 0.0477(10) 0.0545(11) 0.0004(7) 0.0030(7) -0.0288(8)
    O10 0.0375(12) 0.0441(12) 0.260(4) 0.0178(9) 0.0694(18) 0.0316(16)
    C1 0.0221(10) 0.0392(12) 0.0384(12) 0.0037(9) 0.0051(9) -0.0151(9)
    C2 0.0176(9) 0.0314(10) 0.0311(10) 0.0016(8) 0.0035(8) -0.0065(8)
    C3 0.0224(10) 0.0285(10) 0.0274(10) 0.0045(8) 0.0065(8) -0.0024(8)
    C4 0.0199(10) 0.0291(10) 0.0261(10) 0.0022(8) 0.0033(8) -0.0034(8)
    C5 0.0222(10) 0.0336(11) 0.0303(11) 0.0036(8) 0.0050(8) -0.0035(8)
    C6 0.0220(10) 0.0462(13) 0.0383(12) 0.0105(9) 0.0067(9) -0.0024(10)
    C7 0.0226(11) 0.0404(12) 0.0364(12) 0.0021(9) 0.0031(9) -0.0112(10)
    C8 0.0191(10) 0.0379(12) 0.0321(11) 0.0014(8) 0.0025(8) -0.0068(9)
    C9 0.0232(10) 0.0299(10) 0.0331(11) 0.0054(8) 0.0056(8) -0.0026(8)
    C10 0.0214(10) 0.0271(10) 0.0341(11) 0.0025(8) 0.0017(8) -0.0065(8)
    C11 0.0229(11) 0.0287(10) 0.0424(12) 0.0054(8) 0.0026(9) -0.0071(9)
    C12 0.0234(12) 0.0423(14) 0.100(2) 0.0071(10) 0.0091(13) -0.0191(14)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C1 . 1.349(3) ?
    O1 C5 . 1.357(2) ?
    O2 C2 . 1.355(2) ?
    O2 H2 . 0.8200 ?
    O3 C3 . 1.232(2) ?
    O4 C4 . 1.347(2) ?
    O4 H4 . 0.8200 ?
    O5 C6 . 1.416(3) ?
    O5 H5 . 0.8200 ?
    O6 C7 . 1.349(2) ?
    O6 C11 . 1.353(3) ?
    O7 C8 . 1.346(3) ?
    O7 H7 . 0.8200 ?
    O8 C9 . 1.239(3) ?
    O9 C10 . 1.344(2) ?
    O9 H9 . 0.8200 ?
    O10 C12 . 1.283(3) ?
    O10 H10 . 0.8200 ?
    C1 C2 . 1.333(3) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.438(3) ?
    C3 C4 . 1.433(3) ?
    C4 C5 . 1.348(3) ?
    C5 C6 . 1.492(3) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 C8 . 1.331(3) ?
    C7 H7A . 0.9300 ?
    C8 C9 . 1.440(3) ?
    C9 C10 . 1.436(3) ?
    C10 C11 . 1.342(3) ?
    C11 C12 . 1.484(3) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 O1 C5 . . 119.87(17) ?
    C2 O2 H2 . . 109.5 ?
    C4 O4 H4 . . 109.5 ?
    C6 O5 H5 . . 109.5 ?
    C7 O6 C11 . . 118.86(17) ?
    C8 O7 H7 . . 109.5 ?
    C10 O9 H9 . . 109.5 ?
    C12 O10 H10 . . 109.5 ?
    C2 C1 O1 . . 122.39(19) ?
    C2 C1 H1 . . 118.8 ?
    O1 C1 H1 . . 118.8 ?
    C1 C2 O2 . . 120.35(18) ?
    C1 C2 C3 . . 120.67(19) ?
    O2 C2 C3 . . 118.96(18) ?
    O3 C3 C4 . . 122.93(18) ?
    O3 C3 C2 . . 122.27(18) ?
    C4 C3 C2 . . 114.80(18) ?
    O4 C4 C5 . . 119.97(18) ?
    O4 C4 C3 . . 118.79(17) ?
    C5 C4 C3 . . 121.24(18) ?
    C4 C5 O1 . . 121.01(19) ?
    C4 C5 C6 . . 126.97(19) ?
    O1 C5 C6 . . 112.01(18) ?
    O5 C6 C5 . . 111.42(17) ?
    O5 C6 H6A . . 109.3 ?
    C5 C6 H6A . . 109.3 ?
    O5 C6 H6B . . 109.3 ?
    C5 C6 H6B . . 109.3 ?
    H6A C6 H6B . . 108.0 ?
    C8 C7 O6 . . 122.97(18) ?
    C8 C7 H7A . . 118.5 ?
    O6 C7 H7A . . 118.5 ?
    C7 C8 O7 . . 124.02(19) ?
    C7 C8 C9 . . 121.12(19) ?
    O7 C8 C9 . . 114.85(19) ?
    O8 C9 C10 . . 123.02(19) ?
    O8 C9 C8 . . 123.48(19) ?
    C10 C9 C8 . . 113.50(19) ?
    C11 C10 O9 . . 118.14(19) ?
    C11 C10 C9 . . 121.95(19) ?
    O9 C10 C9 . . 119.91(19) ?
    C10 C11 O6 . . 121.58(19) ?
    C10 C11 C12 . . 124.8(2) ?
    O6 C11 C12 . . 113.6(2) ?
    O10 C12 C11 . . 114.2(2) ?
    O10 C12 H12A . . 108.7 ?
    C11 C12 H12A . . 108.7 ?
    O10 C12 H12B . . 108.7 ?
    C11 C12 H12B . . 108.7 ?
    H12A C12 H12B . . 107.6 ?
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
    O2 H2 O5 1_655 0.82 1.85 2.597(2) 151.4
    O2 H2 O3 . 0.82 2.35 2.756(2) 111.5
    O4 H4 O8 2_756 0.82 2.04 2.765(2) 147.9
    O4 H4 O3 . 0.82 2.33 2.755(2) 112.8
    O5 H5 O10 . 0.82 1.85 2.657(3) 168.3
    O7 H7 O2 2_867 0.82 1.85 2.655(2) 166.6
    O9 H9 O3 2_756 0.82 1.90 2.614(2) 145.7
    O9 H9 O8 . 0.82 2.37 2.784(2) 112.0
    O10 H10 O8 1_455 0.82 2.06 2.849(2) 160.7
    O10 H10 O7 1_455 0.82 2.32 2.839(3) 121.9
data_publication_text
_journal_date_recd_electronic     2005-03-24
_journal_date_accepted     2005-04-14
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue      5
_journal_page_first     o1403
_journal_page_last     o1405
_journal_paper_category     EO
_publ_contact_author_name     'Professor Guo-Wei Qin'
_publ_contact_author_address
;Shanghai Institute of Materia Medica,
Shanghai Institutes for Biological Sciences,
Chinese Academy of Sciences, Shanghai 201203, People's Republic of China
;
_publ_contact_author_email     gwqin@mail.shcnc.ac.cn
_publ_contact_author_fax     +86-21-50807088
_publ_contact_author_phone     +86-21-50805853
loop_
    _publ_section_title
;
3,5-Dihydroxy-2-hydroxymethyl-4H-pyran-4-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Yao, Guang-Min'
;Shanghai Institute of Materia Medica,
Shanghai Institutes for Biological Sciences,
Chinese Academy of Sciences, Shanghai 201203, People's Republic of China
;
    'Wang, Yu-Bo'
;Shanghai Institute of Materia Medica,
Shanghai Institutes for Biological Sciences,
Chinese Academy of Sciences, Shanghai 201203, People's Republic of China
;
    'Wang , Li-Quan'
;Shanghai Institute of Materia Medica,
Shanghai Institutes for Biological Sciences,
Chinese Academy of Sciences, Shanghai 201203, People's Republic of China
;
    'Qin, Guo-Wei'
;Shanghai Institute of Materia Medica,
Shanghai Institutes for Biological Sciences,
Chinese Academy of Sciences, Shanghai 201203, People's Republic of China
;
