data_global
_audit_creation_method SHELXL-97
_journal_date_recd_electronic 2006-08-27
_journal_date_accepted 2006-09-11
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2006
_journal_volume 62
_journal_issue 11
_journal_page_first o5315
_journal_page_last o5316
_journal_paper_category EO
_journal_coeditor_code AC2044
_publ_contact_author_name 'Prof. Lu Yang'
_publ_contact_author_address

; Institute of Materia Medica
  Chinese Academy of Medical Sciences
  and Peking Union Medical College
  1 Xiannong Tan Street, Beijing 100050
  People's Republic of China
;
_publ_contact_author_email luy@imm.ac.cn
_publ_contact_author_fax '86 10 6316 5212'
_publ_contact_author_phone '86 10 6316 5212'
_publ_section_title

;
Redetermination of 7,8-dihydroxy-2<i>H</i>-chromen-2-one hemihydrate
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
'Yong-Bin Lu' .
; Institute of Materia Medica
  Chinese Academy of Medical Sciences
  and Peking Union Medical College
  1 Xiannong Tan Street, Beijing 100050
  People's Republic of China
;
'Qi-Tai Zheng' .
; Institute of Materia Medica
  Chinese Academy of Medical Sciences
  and Peking Union Medical College
  1 Xiannong Tan Street, Beijing 100050
  People's Republic of China
;
'Yang Lu' .
; Institute of Materia Medica
  Chinese Academy of Medical Sciences
  and Peking Union Medical College
  1 Xiannong Tan Street, Beijing 100050
  People's Republic of China
;
data_I
_chemical_name_systematic 
;
7,8-dihydroxy-2H-chromen-2-one hemihydrate
;
_chemical_name_common Daphnetin
_chemical_formula_moiety 'C9 H6 O4, 0.5H2 O'
_chemical_formula_sum 'C9 H7 O4.5'
_chemical_formula_iupac 'C9 H6 O4, 0.5H2 O'
_chemical_formula_weight 187.15
_chemical_melting_point ?
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'F d d 2'
_symmetry_space_group_name_Hall 'F 2 -2d'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
_cell_length_a 22.990(3)
_cell_length_b 36.609(5)
_cell_length_c 3.711(3)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 3123(3)
_cell_formula_units_Z 16
_cell_measurement_reflns_used 1066
_cell_measurement_theta_min 2.84
_cell_measurement_theta_max 27.99
_cell_measurement_temperature 298(2)
_exptl_crystal_description prism
_exptl_crystal_colour 'pale yellow'
_exptl_crystal_size_max 0.50
_exptl_crystal_size_mid 0.25
_exptl_crystal_size_min 0.20
_exptl_crystal_density_diffrn 1.592
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1552
_exptl_absorpt_coefficient_mu 0.130
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details 
;
 ?
;
_diffrn_ambient_temperature 298(2)
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'rotating anode'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'MAC DIP 2030K'
_diffrn_measurement_method \w
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number 3924
_diffrn_reflns_av_R_equivalents 0.0450
_diffrn_reflns_av_sigmaI/netI 0.0580
_diffrn_reflns_theta_min 2.84
_diffrn_reflns_theta_max 27.99
_diffrn_reflns_theta_full 27.99
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_limit_h_min -30
_diffrn_reflns_limit_h_max 30
_diffrn_reflns_limit_k_min -46
_diffrn_reflns_limit_k_max 46
_diffrn_reflns_limit_l_min -4
_diffrn_reflns_limit_l_max 4
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% 0
_refine_special_details

;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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 1066
_reflns_number_gt 1048
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0426
_refine_ls_R_factor_gt 0.0425
_refine_ls_wR_factor_gt 0.1103
_refine_ls_wR_factor_ref 0.1104
_refine_ls_goodness_of_fit_ref 1.078
_refine_ls_restrained_S_all 1.078
_refine_ls_number_reflns 1066
_refine_ls_number_parameters 133
_refine_ls_number_restraints 1
_refine_ls_hydrogen_treatment mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0719P)^2^+2.386P] where P=(Fo^2^+2Fc^2^)/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 0.197
_refine_diff_density_min -0.218
_refine_ls_extinction_method SHELXL97
_refine_ls_extinction_coef 0.049(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
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'
_computing_data_collection 'DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement 'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction SCALEPACK
_computing_structure_solution 'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement SHELXL97
_computing_molecular_graphics 'PLATON (Spek, 2003)'
_computing_publication_material SHELXL97
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_disorder_assembly
_atom_site_disorder_group
O O5 0.0000 0.0000 0.7104(8) 0.0431(6) Uani d S 1 . .
H H5O -0.0212(13) 0.0088(9) 0.825(13) 0.065 Uiso d . 1 . .
O O1 0.10359(6) 0.11936(3) 0.2266(5) 0.0368(4) Uani d . 1 . .
O O2 0.10086(7) 0.17879(4) 0.2818(7) 0.0549(6) Uani d . 1 . .
O O3 0.09718(6) -0.00845(4) 0.1731(6) 0.0442(5) Uani d . 1 . .
H H3O 0.1200(13) -0.0270(9) 0.106(13) 0.066 Uiso d . 1 . .
O O4 0.04674(6) 0.05747(4) 0.3330(6) 0.0409(5) Uani d . 1 . .
H H4O 0.0388(12) 0.0383(9) 0.421(12) 0.061 Uiso d . 1 . .
C C2 0.12970(8) 0.15254(5) 0.1830(7) 0.0391(5) Uani d . 1 . .
C C3 0.18754(9) 0.15346(6) 0.0326(8) 0.0451(6) Uani d . 1 . .
H H3 0.2057 0.1758 -0.0047 0.054 Uiso calc R 1 . .
C C4 0.21558(8) 0.12261(6) -0.0541(7) 0.0418(5) Uani d . 1 . .
H H4 0.2530 0.1239 -0.1485 0.050 Uiso calc R 1 . .
C C4A 0.18852(8) 0.08766(5) -0.0031(6) 0.0333(5) Uani d . 1 . .
C C5 0.21528(8) 0.05426(6) -0.0825(7) 0.0386(5) Uani d . 1 . .
H H5 0.2531 0.0538 -0.1718 0.046 Uiso calc R 1 . .
C C6 0.18550(8) 0.02200(5) -0.0279(7) 0.0382(5) Uani d . 1 . .
H H6 0.2029 -0.0002 -0.0854 0.046 Uiso calc R 1 . .
C C7 0.12921(8) 0.02264(5) 0.1135(6) 0.0332(5) Uani d . 1 . .
C C8 0.10157(8) 0.05534(5) 0.2000(7) 0.0322(5) Uani d . 1 . .
C C8A 0.13243(8) 0.08720(4) 0.1380(6) 0.0315(5) Uani 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
O5 0.0362(10) 0.0337(10) 0.0593(15) -0.0015(7) 0.000 0.000
O1 0.0346(6) 0.0233(6) 0.0525(10) -0.0005(4) 0.0088(7) -0.0031(6)
O2 0.0510(8) 0.0274(7) 0.0864(16) -0.0045(5) 0.0161(10) -0.0089(9)
O3 0.0433(7) 0.0249(6) 0.0643(12) 0.0038(5) 0.0048(8) -0.0026(7)
O4 0.0329(7) 0.0254(6) 0.0644(11) 0.0003(4) 0.0112(8) 0.0023(7)
C2 0.0397(9) 0.0235(8) 0.0540(14) -0.0068(6) 0.0043(10) -0.0027(9)
C3 0.0380(9) 0.0372(9) 0.0602(15) -0.0121(7) 0.0123(11) 0.0002(10)
C4 0.0317(8) 0.0457(10) 0.0480(13) -0.0053(7) 0.0062(9) -0.0018(10)
C4A 0.0261(7) 0.0390(9) 0.0347(11) -0.0013(6) 0.0024(8) -0.0031(8)
C5 0.0288(8) 0.0446(10) 0.0423(12) 0.0069(7) 0.0043(9) -0.0020(10)
C6 0.0332(8) 0.0361(9) 0.0454(13) 0.0111(7) -0.0002(9) -0.0050(10)
C7 0.0329(8) 0.0273(8) 0.0394(11) 0.0019(6) -0.0009(9) -0.0007(8)
C8 0.0318(8) 0.0263(8) 0.0385(11) 0.0015(6) -0.0001(8) -0.0011(8)
C8A 0.0289(8) 0.0273(8) 0.0382(11) 0.0024(6) 0.0011(8) -0.0040(8)
_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
O5 H5O . 0.72(4) yes
O1 C2 . 1.364(2) yes
O1 C8A . 1.3908(19) ?
O2 C2 . 1.224(3) yes
O3 C7 . 1.373(2) yes
O3 H3O . 0.89(3) yes
O4 C8 . 1.356(2) yes
O4 H4O . 0.80(4) yes
C2 C3 . 1.443(3) ?
C3 C4 . 1.340(3) ?
C3 H3 . 0.9300 ?
C4 C4A . 1.435(3) ?
C4 H4 . 0.9300 ?
C4A C8A . 1.392(3) ?
C4A C5 . 1.400(3) ?
C5 C6 . 1.380(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.397(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.393(2) yes
C8 C8A . 1.384(2) ?
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
C2 O1 C8A . . 121.06(15) yes
C7 O3 H3O . . 106(2) yes
C8 O4 H4O . . 108(2) yes
O2 C2 O1 . . 115.17(18) ?
O2 C2 C3 . . 126.65(17) ?
O1 C2 C3 . . 118.18(17) yes
C4 C3 C2 . . 121.11(18) yes
C4 C3 H3 . . 119.4 ?
C2 C3 H3 . . 119.4 ?
C3 C4 C4A . . 120.76(18) ?
C3 C4 H4 . . 119.6 ?
C4A C4 H4 . . 119.6 ?
C8A C4A C5 . . 118.40(17) ?
C8A C4A C4 . . 117.52(16) ?
C5 C4A C4 . . 124.08(18) ?
C6 C5 C4A . . 119.91(18) ?
C6 C5 H5 . . 120.0 ?
C4A C5 H5 . . 120.0 ?
C5 C6 C7 . . 120.02(17) yes
C5 C6 H6 . . 120.0 ?
C7 C6 H6 . . 120.0 ?
O3 C7 C8 . . 115.51(16) ?
O3 C7 C6 . . 122.91(16) ?
C8 C7 C6 . . 121.58(17) ?
O4 C8 C8A . . 119.24(15) ?
O4 C8 C7 . . 123.87(16) ?
C8A C8 C7 . . 116.88(17) ?
C8 C8A O1 . . 115.45(15) ?
C8 C8A C4A . . 123.20(16) ?
O1 C8A C4A . . 121.35(15) ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8A O1 C2 O2 . . . . -177.6(2) yes
C8A O1 C2 C3 . . . . 1.7(4) ?
O2 C2 C3 C4 . . . . 177.6(3) ?
O1 C2 C3 C4 . . . . -1.6(4) yes
C2 C3 C4 C4A . . . . 0.6(4) ?
C3 C4 C4A C8A . . . . 0.2(4) yes
C3 C4 C4A C5 . . . . -179.1(2) ?
C8A C4A C5 C6 . . . . 1.5(3) ?
C4 C4A C5 C6 . . . . -179.3(2) yes
C4A C5 C6 C7 . . . . -1.4(4) ?
C5 C6 C7 O3 . . . . 179.8(2) ?
C5 C6 C7 C8 . . . . 0.5(4) ?
O3 C7 C8 O4 . . . . -0.3(4) yes
C6 C7 C8 O4 . . . . 179.0(2) ?
O3 C7 C8 C8A . . . . -179.1(2) ?
C6 C7 C8 C8A . . . . 0.2(3) ?
O4 C8 C8A O1 . . . . 1.0(3) ?
C7 C8 C8A O1 . . . . 179.9(2) ?
O4 C8 C8A C4A . . . . -179.0(2) ?
C7 C8 C8A C4A . . . . -0.1(3) ?
C2 O1 C8A C8 . . . . 179.0(2) yes
C2 O1 C8A C4A . . . . -1.0(3) ?
C5 C4A C8A C8 . . . . -0.7(3) ?
C4 C4A C8A C8 . . . . 180.0(2) ?
C5 C4A C8A O1 . . . . 179.3(2) ?
C4 C4A C8A O1 . . . . 0.0(3) ?
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
O5 H5O O3 2_556 0.72(4) 2.17(4) 2.835(2) 153(4) yes
O3 H3O O2 7_544 0.89(3) 1.77(3) 2.642(2) 163(3) yes
O4 H4O O5 . 0.80(4) 1.98(4) 2.746(2) 162(3) yes
