#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/33/2003308.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_2003308 loop_ _publ_author_name 'Gainsford, G. J.' _publ_section_title ; Antifungal Compounds Isolated from New Zealand Flax: 7-Hydroxy-5-methoxy-6-methylphthalide and 4-Methoxycarbonyl-\b-orcinol ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 709 _journal_page_last 712 _journal_paper_doi 10.1107/S0108270194009753 _journal_volume 51 _journal_year 1995 _chemical_compound_source ; natural product isolated from the powdered roots of Phormium cookianum ; _chemical_formula_moiety 'C10 H10 O4' _chemical_formula_sum 'C10 H10 O4' _chemical_formula_weight 194.2 _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_type_scat_source IntTabC _cell_angle_alpha 81.92(10) _cell_angle_beta 85.05(7) _cell_angle_gamma 79.34(8) _cell_formula_units_Z 8 _cell_length_a 6.985(4) _cell_length_b 16.056(22) _cell_length_c 16.566(17) _cell_measurement_reflns_used 24 _cell_measurement_temperature 133 _cell_measurement_theta_max 13.7 _cell_measurement_theta_min 3.5 _cell_volume 1804(3) _diffrn_measurement_device 'Nicolet R3m' _diffrn_measurement_method \w _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 4827 _diffrn_reflns_theta_max 22.5 _diffrn_standards_decay_% 2 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.12 _exptl_absorpt_correction_type none _exptl_crystal_colour 'light brown' _exptl_crystal_density_diffrn 1.43 _exptl_crystal_description needle _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.26 _refine_diff_density_min -0.26 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 1.110 _refine_ls_hydrogen_treatment refxyz _refine_ls_number_parameters 628 _refine_ls_number_reflns 1653 _refine_ls_R_factor_obs 0.051 _refine_ls_shift/esd_max 0.20 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme ; w = 1/[\s^2^(F~o~)^2^ + 0.0702P^2^] where P = (F~o~^2^ + 2F~o~^2^)/3 ; _refine_ls_wR_factor_obs 0.111 _reflns_number_observed 1653 _reflns_number_total 4665 _reflns_observed_criterion I>3\s(I) _cod_data_source_file as1120.cif _cod_data_source_block as1120a _cod_original_cell_volume 1804(3) _cod_database_code 2003308 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv O(11) .2639(11) .1136(5) .4837(5) .038(2) O(12) .2570(10) -.0265(5) .4972(4) .031(2) O(13) .2723(11) -.0630(5) .8595(4) .034(2) O(14) .2921(12) .1669(5) .6525(4) .033(2) C(11) .2666(17) .0464(7) .5289(7) .030(3) C(12) .2571(19) -.0971(8) .5645(7) .030(3) C(13) .2660(15) -.0578(7) .6393(7) .023(3) C(14) .2659(17) -.0926(7) .7206(7) .028(3) C(15) .2687(15) -.0362(7) .7789(7) .026(3) C(16) .2827(16) .0514(7) .7562(8) .026(3) C(17) .2868(15) .0809(7) .6744(7) .027(3) C(18) .2747(15) .0284(7) .6167(6) .022(3) C(19) .2590(24) -.1512(8) .8871(8) .052(5) C(110) .2868(19) .1069(8) .8206(8) .034(4) O(21) .8158(11) -.6848(4) .9681(5) .038(2) O(22) .7724(11) -.6417(4) 1.0925(5) .037(2) O(23) .6960(12) -.2744(5) .9570(5) .045(2) O(24) .7989(14) -.5260(5) .8384(5) .044(3) C(21) .7870(17) -.6263(7) 1.0103(8) .033(3) C(22) .7374(20) -.5615(8) 1.1256(7) .033(3) C(23) .7367(16) -.4936(8) 1.0544(7) .029(3) C(24) .7134(18) -.4071(8) 1.0490(8) .038(4) C(25) .7180(17) -.3610(7) .9713(8) .033(3) C(26) .7435(16) -.3994(7) .9016(7) .028(3) C(27) .7720(17) -.4888(7) .9068(7) .029(3) C(28) .7649(15) -.5356(7) .9857(7) .025(3) C(29) .6786(21) -.2295(9) 1.0278(10) .051(4) C(210) .7529(21) -.3482(9) .8177(9) .043(4) O(31) .8650(12) .3167(5) .7807(5) .042(2) O(32) .8289(11) .2858(4) .6547(4) .032(2) O(33) .7670(11) -.0749(5) .7856(4) .032(2) O(34) .8274(12) .1633(5) .9073(5) .034(2) C(31) .8388(16) .2665(7) .7367(7) .028(3) C(32) .8017(18) .2092(8) .6203(7) .033(3) C(33) .7962(15) .1405(7) .6922(7) .025(3) C(34) .7796(15) .0567(7) .6951(7) .025(3) C(35) .7814(16) .0097(7) .7719(7) .027(3) C(36) .7892(16) .0457(7) .8444(7) .027(3) C(37) .8108(16) .1285(7) .8371(7) .028(3) C(38) .8143(16) .1783(7) .7613(7) .027(3) C(39) .7711(20) -.1159(8) .7143(8) .034(4) C(310) .7836(22) -.0076(9) .9275(8) .043(4) O(41) .3620(10) .2834(5) .5080(4) .034(2) O(42) .3932(10) .4219(5) .4867(4) .031(2) O(43) -.3180(11) .5225(4) .2968(4) .031(2) O(44) .0124(11) .2590(4) .4192(4) .030(2) C(41) .3015(7) .3574(8) .4771(6) .030(6) C(42) .2875(18) .5010(7) .4433(7) .029(3) C(43) .1230(16) .4750(6) .4092(6) .020(3) C(44) -.0258(18) .5231(7) .3651(7) .028(3) C(45) -.1625(16) .4809(7) .3404(6) .023(3) C(46) -.1547(16) .3916(7) .3587(6) .019(3) C(47) .0029(17) .3459(6) .4026(6) .026(3) C(48) .1367(16) .3879(6) .4287(6) .022(3) C(49) -.3461(20) .6140(8) .2800(8) .038(4) C(410) -.3019(19) .3466(8) .3317(8) .033(3) H(014) .2998(146) .1743(63) .6056(56) .016(17) H12A .1338(119) -.1210(49) .5557(47) .008(7) H12B .3690(123) -.1263(53) .5592(53) .008(7) H14 .2659(114) -.1525(52) .7414(48) .008(7) H19A .1397(165) -.1693(70) .8694(67) .053(8) H19B .2490(136) -.1429(60) .9608(64) .053(8) H19C .3385(172) -.1895(72) .8681(68) .053(8) H11A .1993(141) .0824(61) .8890(64) .053(8) H11B .2942(155) .1649(71) .7947(67) .053(8) H11C .4027(157) .1005(74) .8357(67) .053(8) H(024) .8166(147) -.5703(58) .8330(63) .016(17) H22A .8351(118) -.5555(51) 1.1625(50) .008(7) H22B .6055(115) -.5559(46) 1.1748(48) .008(7) H24 .7110(117) -.3781(51) 1.0960(51) .008(7) H29A .7830(156) -.2397(68) 1.0692(66) .053(8) H29B .6834(150) -.1657(69) .9940(65) .053(8) H29C .5583(165) -.2197(72) 1.0395(72) .053(8) H21A .6261(163) -.3115(66) .8132(64) .053(8) H21B .8475(159) -.3144(69) .8154(65) .053(8) H21C .7842(156) -.3788(67) .7715(67) .053(8) H(034) .8035(137) .2163(58) .8984(56) .016(17) H32A .6546(119) .2213(47) .5869(46) .008(7) H32B .8823(125) .2015(55) .5810(50) .008(7) H34 .7838(109) .0365(47) .6353(50) .008(7) H39A .6681(162) -.0888(68) .6768(64) .053(8) H39B .8977(157) -.1080(61) .6719(63) .053(8) H39C .7703(158) -.1692(71) .7361(67) .053(8) H31A .7528(155) .0226(65) .9799(66) .053(8) H31B .6686(162) -.0343(69) .9328(67) .053(8) H31C .8670(173) -.0456(71) .9179(73) .1053(8) H(044) .1281(129) .2340(56) .4477(52) .016(17) H42A .3867(120) .5228(49) .4031(48) .008(7) H42B .2444(113) .5443(51) .4884(49) .008(7) H44 -.0368(123) .5743(51) .3524(48) .008(7) H49A -.2252(161) .6337(67) .2531(65) .053(8) H49B -.3381(148) .6398(65) .3330(66) .053(8) H49C -.4514(155) .6303(62) .2418(63) .053(8) H41A -.4244(161) .3786(66) .3120(64) .053(8) H41B -.2463(158) .3123(69) .2913(66) .053(8) H41C -.3045(150) .2990(69) .3784(65) .053(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O(11) C(11) 1.222(12) yes O(12) C(11) 1.363(12) yes O(12) C(12) 1.474(12) yes O(13) C(15) 1.345(12) yes O(13) C(19) 1.443(14) yes O(14) C(17) 1.384(13) yes O(14) H(014) 0.77(9) no C(11) C(18) 1.447(14) yes C(12) C(13) 1.48(2) yes C(13) C(14) 1.383(14) yes C(13) C(18) 1.392(14) yes C(14) C(15) 1.418(14) yes C(15) C(16) 1.423(14) yes C(16) C(17) 1.37(2) yes C(16) C(110) 1.49(2) yes C(17) C(18) 1.378(14) yes O(21) C(21) 1.226(12) yes O(22) C(21) 1.348(13) yes O(22) C(22) 1.441(12) yes O(23) C(25) 1.359(12) yes O(23) C(29) 1.45(2) yes O(24) C(27) 1.337(13) yes O(24) H(024) 0.72(9) no C(21) C(28) 1.440(14) yes C(22) C(23) 1.49(2) yes C(23) C(24) 1.36(2) yes C(23) C(28) 1.384(14) yes C(24) C(25) 1.39(2) yes C(25) C(26) 1.37(2) yes C(26) C(27) 1.40(2) yes C(26) C(210) 1.52(2) yes C(27) C(28) 1.415(14) yes O(31) C(31) 1.207(12) yes O(32) C(31) 1.354(12) yes O(32) C(32) 1.475(14) yes O(33) C(35) 1.367(12) yes O(33) C(39) 1.427(14) yes O(34) C(37) 1.382(13) yes O(34) H(034) 0.83(9) no C(31) C(38) 1.454(14) yes C(32) C(33) 1.508(14) yes C(33) C(34) 1.37(2) yes C(33) C(38) 1.39(2) yes C(34) C(35) 1.384(14) yes C(35) C(36) 1.41(2) yes C(36) C(37) 1.353(14) yes C(36) C(310) 1.52(2) yes C(37) C(38) 1.392(14) yes O(41) C(41) 1.237(12) yes O(42) C(41) 1.349(12) yes O(42) C(42) 1.470(12) yes O(43) C(45) 1.370(12) yes O(43) C(49) 1.435(13) yes O(44) C(47) 1.374(11) yes O(44) H(044) 0.96(9) no C(41) C(48) 1.43(2) yes C(42) C(43) 1.47(2) yes C(43) C(44) 1.373(14) yes C(43) C(48) 1.378(14) yes C(44) C(45) 1.387(14) yes C(45) C(46) 1.414(13) yes C(46) C(47) 1.404(14) yes C(46) C(410) 1.49(2) yes C(47) C(48) 1.378(14) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139054205