data_2014353
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2006
_journal_volume  62
_journal_page_first  o86
_journal_page_last  o88
_publ_section_title
;
7-Hydroxy-6-methoxy-2-oxo-2<i>H</i>-chromen-3-yl 2-oxo-2<i>H</i>-chromen-7-yl
ether
;
loop_
_publ_author_name
  'Tian-Zhu Zhang'
  'Chun-Yan Wei'
  'Guo-Hai Xu'
  'Se-Won Park'
_chemical_name_common  Daphnoretin
_chemical_formula_moiety  'C19 H12 O7'
_chemical_formula_sum  'C19 H12 O7'
_chemical_formula_iupac  'C19 H12 O7'
_chemical_formula_weight  352.29
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  7.659(3)
_cell_length_b  13.872(5)
_cell_length_c  16.479(5)
_cell_angle_alpha  113.175(5)
_cell_angle_beta  99.171(6)
_cell_angle_gamma  96.799(5)
_cell_volume  1557.0(10)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.503
_diffrn_ambient_temperature  293(2)
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
  C1A 0.4428(2) 0.27260(14) 0.00204(13) 0.0388(5) Uani d . 1 . . C
  C2A 0.4862(2) 0.28008(14) 0.08964(12) 0.0415(5) Uani d . 1 . . C
  H2A 0.4467 0.3303 0.1360 0.050 Uiso calc R 1 . . H
  C3A 0.5883(2) 0.21244(15) 0.10721(12) 0.0427(5) Uani d . 1 . . C
  H3A 0.6198 0.2185 0.1662 0.051 Uiso calc R 1 . . H
  C4A 0.6458(2) 0.13477(14) 0.03831(12) 0.0375(5) Uani d . 1 . . C
  C5A 0.7443(2) 0.05791(15) 0.04906(13) 0.0452(5) Uani d . 1 . . C
  H5A 0.7830 0.0612 0.1067 0.054 Uiso calc R 1 . . H
  C6A 0.7825(2) -0.01894(15) -0.02211(14) 0.0460(5) Uani d . 1 . . C
  H6A 0.8441 -0.0692 -0.0134 0.055 Uiso calc R 1 . . H
  C7A 0.7295(3) -0.02455(16) -0.11155(15) 0.0473(5) Uani d . 1 . . C
  C8A 0.5936(2) 0.12851(14) -0.04881(12) 0.0363(4) Uani d . 1 . . C
  C9A 0.4956(2) 0.19686(14) -0.06798(12) 0.0414(5) Uani d . 1 . . C
  H9A 0.4659 0.1921 -0.1266 0.050 Uiso calc R 1 . . H
  C10A 0.2349(3) 0.39021(15) 0.03182(12) 0.0402(5) Uani d . 1 . . C
  C11A 0.2546(3) 0.49625(15) 0.07293(12) 0.0416(5) Uani d . 1 . . C
  H11A 0.3566 0.5399 0.0729 0.050 Uiso calc R 1 . . H
  C12A 0.1196(2) 0.54341(14) 0.11712(11) 0.0365(4) Uani d . 1 . . C
  C13A 0.1265(3) 0.65387(14) 0.16137(12) 0.0411(5) Uani d . 1 . . C
  H13A 0.2248 0.7017 0.1633 0.049 Uiso calc R 1 . . H
  C14A -0.0092(3) 0.69260(14) 0.20180(12) 0.0390(5) Uani d . 1 . . C
  C15A -0.1591(3) 0.62015(15) 0.19821(12) 0.0401(5) Uani d . 1 . . C
  C16A -0.1681(3) 0.51251(15) 0.15469(12) 0.0426(5) Uani d . 1 . . C
  H16A -0.2671 0.4647 0.1521 0.051 Uiso calc R 1 . . H
  C17A -0.0310(2) 0.47467(14) 0.11472(11) 0.0368(4) Uani d . 1 . . C
  C18A 0.0779(3) 0.31726(16) 0.02885(12) 0.0418(5) Uani d . 1 . . C
  C19A 0.1020(3) 0.87447(15) 0.23345(14) 0.0645(7) Uani d . 1 . . C
  H19A 0.0863 0.9452 0.2695 0.097 Uiso calc R 1 . . H
  H19B 0.0729 0.8607 0.1705 0.097 Uiso calc R 1 . . H
  H19C 0.2251 0.8690 0.2502 0.097 Uiso calc R 1 . . H
  C1B 0.5733(2) 0.73632(15) 0.52152(13) 0.0397(5) Uani d . 1 . . C
  C2B 0.4670(3) 0.70613(15) 0.43583(13) 0.0477(5) Uani d . 1 . . C
  H2B 0.4705 0.6422 0.3884 0.057 Uiso calc R 1 . . H
  C3B 0.3567(3) 0.77144(16) 0.42168(13) 0.0474(5) Uani d . 1 . . C
  H3B 0.2833 0.7505 0.3645 0.057 Uiso calc R 1 . . H
  C4B 0.3520(2) 0.86928(15) 0.49170(12) 0.0380(5) Uani d . 1 . . C
  C5B 0.2409(2) 0.94177(16) 0.48333(14) 0.0466(5) Uani d . 1 . . C
  H5B 0.1605 0.9236 0.4285 0.056 Uiso calc R 1 . . H
  C6B 0.2502(3) 1.03592(16) 0.55316(14) 0.0477(5) Uani d . 1 . . C
  H6B 0.1773 1.0822 0.5457 0.057 Uiso calc R 1 . . H
  C7B 0.3707(3) 1.06612(16) 0.63905(14) 0.0439(5) Uani d . 1 . . C
  C8B 0.4660(2) 0.89720(14) 0.57563(12) 0.0353(4) Uani d . 1 . . C
  C9B 0.5745(2) 0.83201(14) 0.59251(12) 0.0381(5) Uani d . 1 . . C
  H9B 0.6464 0.8517 0.6498 0.046 Uiso calc R 1 . . H
  C10B 0.7610(2) 0.60870(14) 0.47727(12) 0.0387(5) Uani d . 1 . . C
  C11B 0.7399(2) 0.50301(14) 0.44958(12) 0.0400(5) Uani d . 1 . . C
  H11B 0.6547 0.4673 0.4678 0.048 Uiso calc R 1 . . H
  C12B 0.8476(2) 0.44413(14) 0.39195(11) 0.0366(4) Uani d . 1 . . C
  C13B 0.8397(2) 0.33368(14) 0.36197(12) 0.0397(5) Uani d . 1 . . C
  H13B 0.7579 0.2938 0.3786 0.048 Uiso calc R 1 . . H
  C14B 0.9511(3) 0.28363(14) 0.30831(12) 0.0389(5) Uani d . 1 . . C
  C15B 1.0766(3) 0.34384(15) 0.28321(12) 0.0399(5) Uani d . 1 . . C
  C16B 1.0861(3) 0.45151(15) 0.31245(12) 0.0421(5) Uani d . 1 . . C
  H16B 1.1686 0.4916 0.2964 0.051 Uiso calc R 1 . . H
  C17B 0.9727(2) 0.50083(14) 0.36602(11) 0.0373(5) Uani d . 1 . . C
  C18B 0.8914(3) 0.66903(15) 0.45085(13) 0.0425(5) Uani d . 1 . . C
  C19B 0.8331(3) 0.11117(15) 0.29726(13) 0.0601(6) Uani d . 1 . . C
  H19D 0.8481 0.0384 0.2697 0.090 Uiso calc R 1 . . H
  H19E 0.7111 0.1152 0.2760 0.090 Uiso calc R 1 . . H
  H19F 0.8585 0.1356 0.3619 0.090 Uiso calc R 1 . . H
  O1A 0.35292(18) 0.34319(10) -0.01971(8) 0.0502(4) Uani d . 1 . . O
  O1B 0.67541(18) 0.66934(10) 0.54187(8) 0.0477(4) Uani d . 1 . . O
  O2A 0.63689(18) 0.05040(10) -0.12140(8) 0.0480(4) Uani d . 1 . . O
  O3A 0.7580(2) -0.08925(12) -0.18021(10) 0.0708(5) Uani d . 1 . . O
  O4A 0.04948(18) 0.22080(10) -0.00833(9) 0.0538(4) Uani d . 1 . . O
  O5A -0.04808(17) 0.36499(9) 0.07215(8) 0.0451(3) Uani d . 1 . . O
  O6A -0.29514(19) 0.65470(12) 0.23758(10) 0.0580(4) Uani d . 1 . . O
  O7A -0.01414(18) 0.79814(10) 0.24851(9) 0.0555(4) Uani d . 1 . . O
  O2B 0.47407(16) 0.99413(9) 0.64707(8) 0.0431(3) Uani d . 1 . . O
  O3B 0.39180(19) 1.14857(11) 0.70653(10) 0.0604(4) Uani d . 1 . . O
  O4B 0.92093(18) 0.76494(10) 0.47495(9) 0.0573(4) Uani d . 1 . . O
  O5B 0.98931(17) 0.61015(9) 0.39376(8) 0.0462(3) Uani d . 1 . . O
  O6B 1.1873(2) 0.29731(13) 0.23072(10) 0.0575(4) Uani d . 1 . . O
  O7B 0.95408(18) 0.17695(10) 0.27386(9) 0.0520(4) Uani d . 1 . . O
  H6OB 1.173(3) 0.2285(17) 0.2160(14) 0.076(8) Uiso d . 1 . . H
  H6OA -0.288(3) 0.7247(17) 0.2602(14) 0.078(8) Uiso d . 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
  C1A 0.0400(11) 0.0369(11) 0.0457(12) 0.0147(9) 0.0174(9) 0.0188(10)
  C2A 0.0431(12) 0.0373(11) 0.0383(11) 0.0086(9) 0.0153(9) 0.0077(9)
  C3A 0.0404(12) 0.0479(13) 0.0366(11) 0.0083(10) 0.0076(9) 0.0150(10)
  C4A 0.0333(11) 0.0369(11) 0.0416(11) 0.0063(9) 0.0113(9) 0.0149(9)
  C5A 0.0367(12) 0.0515(13) 0.0494(13) 0.0093(10) 0.0063(9) 0.0243(11)
  C6A 0.0381(12) 0.0424(12) 0.0665(14) 0.0146(9) 0.0167(10) 0.0285(11)
  C7A 0.0496(13) 0.0404(12) 0.0642(15) 0.0206(10) 0.0292(11) 0.0250(11)
  C8A 0.0396(11) 0.0331(11) 0.0393(11) 0.0131(9) 0.0198(9) 0.0128(9)
  C9A 0.0495(13) 0.0436(12) 0.0410(12) 0.0200(10) 0.0221(9) 0.0206(10)
  C10A 0.0465(12) 0.0407(12) 0.0414(11) 0.0212(9) 0.0191(9) 0.0185(10)
  C11A 0.0424(12) 0.0402(12) 0.0454(12) 0.0122(9) 0.0155(9) 0.0180(10)
  C12A 0.0393(11) 0.0343(11) 0.0369(11) 0.0103(9) 0.0105(8) 0.0145(9)
  C13A 0.0428(12) 0.0315(11) 0.0460(12) 0.0047(9) 0.0141(9) 0.0123(9)
  C14A 0.0485(12) 0.0277(10) 0.0378(11) 0.0107(9) 0.0118(9) 0.0090(9)
  C15A 0.0418(12) 0.0388(12) 0.0426(12) 0.0153(9) 0.0162(9) 0.0156(10)
  C16A 0.0409(12) 0.0349(11) 0.0527(12) 0.0077(9) 0.0168(9) 0.0167(10)
  C17A 0.0441(12) 0.0278(10) 0.0377(11) 0.0105(9) 0.0091(9) 0.0119(9)
  C18A 0.0485(13) 0.0374(12) 0.0404(12) 0.0177(10) 0.0113(9) 0.0144(10)
  C19A 0.0850(18) 0.0335(12) 0.0700(15) 0.0047(11) 0.0184(13) 0.0183(11)
  C1B 0.0388(11) 0.0383(11) 0.0457(12) 0.0135(9) 0.0167(9) 0.0171(10)
  C2B 0.0468(13) 0.0394(12) 0.0457(13) 0.0118(10) 0.0113(10) 0.0053(10)
  C3B 0.0434(12) 0.0499(13) 0.0409(12) 0.0094(10) 0.0063(9) 0.0123(10)
  C4B 0.0312(11) 0.0422(12) 0.0444(12) 0.0096(9) 0.0132(9) 0.0198(10)
  C5B 0.0392(12) 0.0548(14) 0.0523(13) 0.0113(10) 0.0117(10) 0.0283(11)
  C6B 0.0423(12) 0.0485(13) 0.0667(15) 0.0208(10) 0.0196(11) 0.0330(12)
  C7B 0.0484(13) 0.0374(12) 0.0576(14) 0.0193(10) 0.0268(11) 0.0234(11)
  C8B 0.0383(11) 0.0303(10) 0.0388(11) 0.0103(8) 0.0164(9) 0.0121(9)
  C9B 0.0403(11) 0.0381(11) 0.0367(11) 0.0143(9) 0.0111(9) 0.0139(9)
  C10B 0.0424(12) 0.0359(11) 0.0398(11) 0.0168(9) 0.0149(9) 0.0135(9)
  C11B 0.0421(12) 0.0364(11) 0.0462(12) 0.0123(9) 0.0184(9) 0.0178(9)
  C12B 0.0401(11) 0.0346(11) 0.0355(11) 0.0125(9) 0.0129(9) 0.0121(9)
  C13B 0.0457(12) 0.0331(11) 0.0426(11) 0.0100(9) 0.0181(9) 0.0147(9)
  C14B 0.0498(12) 0.0308(10) 0.0367(11) 0.0127(9) 0.0135(9) 0.0119(9)
  C15B 0.0457(12) 0.0422(12) 0.0366(11) 0.0166(9) 0.0192(9) 0.0155(9)
  C16B 0.0474(12) 0.0404(12) 0.0463(12) 0.0117(9) 0.0219(9) 0.0211(10)
  C17B 0.0433(12) 0.0308(11) 0.0400(11) 0.0116(9) 0.0119(9) 0.0153(9)
  C18B 0.0441(12) 0.0358(12) 0.0491(12) 0.0150(9) 0.0113(10) 0.0174(10)
  C19B 0.0914(18) 0.0354(12) 0.0614(14) 0.0152(11) 0.0331(13) 0.0216(11)
  O1A 0.0660(10) 0.0501(9) 0.0538(9) 0.0333(7) 0.0335(7) 0.0282(7)
  O1B 0.0613(9) 0.0429(8) 0.0482(8) 0.0294(7) 0.0238(7) 0.0192(7)
  O2A 0.0629(9) 0.0454(8) 0.0472(8) 0.0286(7) 0.0284(7) 0.0203(7)
  O3A 0.1042(13) 0.0601(10) 0.0692(11) 0.0515(9) 0.0498(10) 0.0277(9)
  O4A 0.0625(10) 0.0322(8) 0.0603(9) 0.0172(7) 0.0142(7) 0.0107(7)
  O5A 0.0480(8) 0.0291(7) 0.0572(9) 0.0118(6) 0.0200(7) 0.0128(7)
  O6A 0.0576(10) 0.0388(9) 0.0806(11) 0.0196(7) 0.0374(8) 0.0170(9)
  O7A 0.0640(10) 0.0294(8) 0.0684(10) 0.0110(7) 0.0284(8) 0.0104(7)
  O2B 0.0502(8) 0.0351(8) 0.0452(8) 0.0186(6) 0.0150(6) 0.0136(6)
  O3B 0.0805(11) 0.0434(9) 0.0607(10) 0.0322(8) 0.0276(8) 0.0154(8)
  O4B 0.0606(10) 0.0321(8) 0.0806(11) 0.0145(7) 0.0231(8) 0.0208(8)
  O5B 0.0530(9) 0.0332(7) 0.0609(9) 0.0155(6) 0.0262(7) 0.0216(7)
  O6B 0.0720(11) 0.0480(10) 0.0654(10) 0.0272(8) 0.0446(8) 0.0220(8)
  O7B 0.0690(10) 0.0330(8) 0.0588(9) 0.0171(7) 0.0339(7) 0.0148(7)
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
  C1A C9A . 1.376(2) ?
  C1A O1A . 1.385(2) ?
  C1A C2A . 1.388(2) ?
  C2A C3A . 1.375(3) ?
  C2A H2A . 0.9300 ?
  C3A C4A . 1.397(2) ?
  C3A H3A . 0.9300 ?
  C4A C8A . 1.393(2) ?
  C4A C5A . 1.426(3) ?
  C5A C6A . 1.340(2) ?
  C5A H5A . 0.9300 ?
  C6A C7A . 1.433(3) ?
  C6A H6A . 0.9300 ?
  C7A O3A . 1.208(2) ?
  C7A O2A . 1.372(2) ?
  C8A C9A . 1.375(2) ?
  C8A O2A . 1.3808(19) ?
  C9A H9A . 0.9300 ?
  C10A C11A . 1.333(2) ?
  C10A O1A . 1.383(2) ?
  C10A C18A . 1.458(3) ?
  C11A C12A . 1.433(2) ?
  C11A H11A . 0.9300 ?
  C12A C17A . 1.391(2) ?
  C12A C13A . 1.404(2) ?
  C13A C14A . 1.372(2) ?
  C13A H13A . 0.9300 ?
  C14A O7A . 1.369(2) ?
  C14A C15A . 1.411(2) ?
  C15A O6A . 1.351(2) ?
  C15A C16A . 1.366(2) ?
  C16A C17A . 1.375(2) ?
  C16A H16A . 0.9300 ?
  C17A O5A . 1.381(2) ?
  C18A O4A . 1.207(2) ?
  C18A O5A . 1.370(2) ?
  C19A O7A . 1.424(2) ?
  C19A H19A . 0.9600 ?
  C19A H19B . 0.9600 ?
  C19A H19C . 0.9600 ?
  C1B C9B . 1.379(2) ?
  C1B C2B . 1.386(2) ?
  C1B O1B . 1.386(2) ?
  C2B C3B . 1.369(3) ?
  C2B H2B . 0.9300 ?
  C3B C4B . 1.402(2) ?
  C3B H3B . 0.9300 ?
  C4B C8B . 1.392(2) ?
  C4B C5B . 1.424(3) ?
  C5B C6B . 1.343(2) ?
  C5B H5B . 0.9300 ?
  C6B C7B . 1.434(3) ?
  C6B H6B . 0.9300 ?
  C7B O3B . 1.212(2) ?
  C7B O2B . 1.378(2) ?
  C8B C9B . 1.374(2) ?
  C8B O2B . 1.3817(19) ?
  C9B H9B . 0.9300 ?
  C10B C11B . 1.333(2) ?
  C10B O1B . 1.385(2) ?
  C10B C18B . 1.454(3) ?
  C11B C12B . 1.431(2) ?
  C11B H11B . 0.9300 ?
  C12B C17B . 1.391(2) ?
  C12B C13B . 1.403(2) ?
  C13B C14B . 1.375(2) ?
  C13B H13B . 0.9300 ?
  C14B O7B . 1.365(2) ?
  C14B C15B . 1.414(2) ?
  C15B O6B . 1.345(2) ?
  C15B C16B . 1.366(2) ?
  C16B C17B . 1.382(2) ?
  C16B H16B . 0.9300 ?
  C17B O5B . 1.384(2) ?
  C18B O4B . 1.210(2) ?
  C18B O5B . 1.371(2) ?
  C19B O7B . 1.425(2) ?
  C19B H19D . 0.9600 ?
  C19B H19E . 0.9600 ?
  C19B H19F . 0.9600 ?
  O6A H6OA . 0.88(2) ?
  O6B H6OB . 0.87(2) ?