#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/08/2200850.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_2200850 loop_ _publ_author_name 'Langer, Vratislav' 'Lundquist, Knut' 'Stomberg, Rolf' 'von Unge, Sverker' _publ_section_title threo-2-(2,6-Dimethoxyphenoxy)-1-(3,4-dimethoxyphenyl)-1,3-propanediol _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o90 _journal_page_last o92 _journal_paper_doi 10.1107/S1600536801021869 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C19 H24 O7' _chemical_formula_moiety 'C19 H24 O7' _chemical_formula_sum 'C19 H24 O7' _chemical_formula_weight 364.38 _chemical_melting_point 384.0(10) _chemical_name_systematic ; threo-2-(2,6-dimethoxyphenoxy)-1-(3,4-dimethoxyphenyl)-1,3-propanediol ; _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_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 98.9130(10) _cell_angle_beta 90.6640(10) _cell_angle_gamma 97.3280(10) _cell_formula_units_Z 2 _cell_length_a 6.1632(2) _cell_length_b 9.1891(3) _cell_length_c 15.9231(5) _cell_measurement_reflns_used 3859 _cell_measurement_temperature 183(2) _cell_measurement_theta_max 25.36 _cell_measurement_theta_min 2.26 _cell_volume 883.17(5) _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_collection 'SMART (Siemens, 1995)' _computing_data_reduction 'SAINT and SADABS (Sheldrick, 2001)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2000)' _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Bruker, 1997)' _diffrn_ambient_temperature 183(2) _diffrn_measured_fraction_theta_full .996 _diffrn_measured_fraction_theta_max .996 _diffrn_measurement_device_type 'Siemens SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0493 _diffrn_reflns_av_sigmaI/netI .0574 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 9676 _diffrn_reflns_theta_full 25.36 _diffrn_reflns_theta_max 25.36 _diffrn_reflns_theta_min 2.26 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .104 _exptl_absorpt_correction_T_max .998 _exptl_absorpt_correction_T_min .974 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2001)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 388 _exptl_crystal_size_max .25 _exptl_crystal_size_mid .10 _exptl_crystal_size_min .02 _refine_diff_density_max .242 _refine_diff_density_min -.245 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 265 _refine_ls_number_reflns 3238 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.012 _refine_ls_R_factor_all .0930 _refine_ls_R_factor_gt .0506 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0549P)^2^+0.2595P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .1033 _refine_ls_wR_factor_ref .1226 _reflns_number_gt 2141 _reflns_number_total 3238 _reflns_threshold_expression I>2\s(I) _cod_data_source_file cf6139.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '383--385 k' was changed to '384.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '383--385 k' was changed to '384.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2200850 _cod_database_fobs_code 2200850 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 _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 .6522(3) .14298(18) .43995(10) .0314(4) Uani d . 1 . . O O2 .3351(3) .27379(18) .50668(10) .0308(4) Uani d . 1 . . O O4 .4691(3) .4288(2) .12904(10) .0311(4) Uani d . 1 . . O H4 .4852 .5220 .1346 .055(10) Uiso calc R 1 . . H O5 1.0232(3) .36028(18) .08185(11) .0327(4) Uani d . 1 . . O H5 1.1551 .3630 .0968 .078(13) Uiso calc R 1 . . H O6 .7514(3) .63594(17) .22359(10) .0246(4) Uani d . 1 . . O O7 .5561(3) .75577(19) .10900(11) .0357(5) Uani d . 1 . . O O8 1.1417(3) .75625(19) .29620(10) .0316(4) Uani d . 1 . . O C1 .5385(4) .3545(2) .26737(14) .0225(5) Uani d . 1 . . C C2 .6366(4) .2583(2) .31201(15) .0232(5) Uani d . 1 . . C H2 .7522 .2091 .2871 .024(6) Uiso calc R 1 . . H C3 .5677(4) .2342(2) .39138(15) .0222(5) Uani d . 1 . . C C4 .3942(4) .3062(3) .42818(15) .0239(6) Uani d . 1 . . C C5 .2975(4) .3999(3) .38396(15) .0276(6) Uani d . 1 . . C H5A .1801 .4480 .4080 .031(7) Uiso calc R 1 . . H C6 .3707(4) .4245(3) .30421(15) .0266(6) Uani d . 1 . . C H6 .3038 .4904 .2749 .028(7) Uiso calc R 1 . . H C7 .8202(4) .0615(3) .40389(17) .0320(6) Uani d . 1 . . C H7A .7692 .0054 .3482 .028(7) Uiso calc R 1 . . H H7B .8556 -.0074 .4416 .036(7) Uiso calc R 1 . . H H7C .9512 .1307 .3970 .045(8) Uiso calc R 1 . . H C8 .1777(4) .3569(3) .55063(16) .0339(7) Uani d . 1 . . C H8A .2278 .4634 .5546 .036(7) Uiso calc R 1 . . H H8B .1611 .3314 .6079 .048(8) Uiso calc R 1 . . H H8C .0365 .3327 .5194 .045(8) Uiso calc R 1 . . H C9 .6282(4) .3826(3) .18235(15) .0236(5) Uani d . 1 . . C H9 .6702 .2868 .1524 .021(6) Uiso calc R 1 . . H C10 .8333(4) .4970(2) .19224(15) .0231(5) Uani d . 1 . . C H10 .9346 .4735 .2363 .013(5) Uiso calc R 1 . . H C11 .9529(4) .5015(3) .10974(16) .0279(6) Uani d . 1 . . C H11A .8544 .5257 .0658 .025(6) Uiso calc R 1 . . H H11B 1.0811 .5795 .1187 .025(6) Uiso calc R 1 . . H C12 .8552(4) .7668(2) .20159(14) .0236(5) Uani d . 1 . . C C13 .7491(4) .8344(3) .14312(15) .0285(6) Uani d . 1 . . C C14 .8424(5) .9714(3) .12468(17) .0360(7) Uani d . 1 . . C H14 .7725 1.0186 .0848 .041(8) Uiso calc R 1 . . H C15 1.0373(5) 1.0381(3) .16485(17) .0369(7) Uani d . 1 . . C H15 1.0991 1.1323 .1527 .041(7) Uiso calc R 1 . . H C16 1.1461(4) .9718(3) .22248(17) .0335(6) Uani d . 1 . . C H16 1.2811 1.0193 .2489 .036(7) Uiso calc R 1 . . H C17 1.0536(4) .8346(3) .24077(15) .0260(6) Uani d . 1 . . C C18 .4469(5) .8156(3) .04459(18) .0431(7) Uani d . 1 . . C H18A .4119 .9146 .0680 .051(9) Uiso calc R 1 . . H H18B .3115 .7502 .0254 .056(9) Uiso calc R 1 . . H H18C .5427 .8229 -.0037 .057(9) Uiso calc R 1 . . H C19 1.3403(4) .8243(3) .34151(18) .0400(7) Uani d . 1 . . C H19A 1.4571 .8377 .3011 .048(8) Uiso calc R 1 . . H H19B 1.3819 .7606 .3813 .045(8) Uiso calc R 1 . . H H19C 1.3178 .9213 .3731 .052(9) 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 .0360(11) .0308(10) .0317(10) .0134(8) .0071(8) .0099(8) O2 .0332(10) .0331(10) .0283(10) .0089(8) .0126(8) .0075(8) O4 .0271(10) .0346(11) .0320(10) .0021(8) -.0045(8) .0081(8) O5 .0287(11) .0276(10) .0426(11) .0089(8) .0054(9) .0040(8) O6 .0223(9) .0213(9) .0307(9) .0029(7) .0051(7) .0052(7) O7 .0331(11) .0357(10) .0401(11) .0057(8) -.0100(8) .0114(8) O8 .0249(10) .0339(10) .0353(10) -.0018(8) -.0043(8) .0082(8) C1 .0217(13) .0171(12) .0273(13) -.0020(10) .0021(10) .0026(10) C2 .0176(13) .0205(12) .0309(14) .0031(10) .0045(10) .0014(10) C3 .0220(13) .0171(11) .0270(13) .0016(10) -.0014(10) .0032(10) C4 .0218(13) .0231(13) .0253(13) -.0005(11) .0040(10) .0018(10) C5 .0191(13) .0305(14) .0338(15) .0065(11) .0069(11) .0033(11) C6 .0232(13) .0238(13) .0343(15) .0054(11) .0003(11) .0080(11) C7 .0298(15) .0287(14) .0392(16) .0129(12) -.0015(12) .0032(12) C8 .0330(16) .0356(16) .0306(15) .0022(13) .0101(12) -.0016(12) C9 .0223(13) .0215(13) .0276(13) .0037(10) .0030(10) .0049(10) C10 .0218(13) .0214(12) .0280(13) .0057(10) .0028(10) .0075(10) C11 .0270(14) .0239(13) .0359(15) .0082(11) .0068(11) .0099(11) C12 .0245(13) .0206(13) .0257(13) .0031(11) .0055(11) .0028(10) C13 .0302(15) .0267(14) .0294(14) .0083(12) .0023(11) .0027(11) C14 .0445(18) .0280(15) .0393(16) .0123(13) .0043(13) .0105(12) C15 .0472(18) .0193(13) .0461(17) .0040(12) .0124(14) .0102(12) C16 .0325(16) .0248(14) .0408(16) -.0011(12) .0090(13) .0016(12) C17 .0282(14) .0236(13) .0263(14) .0053(11) .0054(11) .0024(10) C18 .0461(19) .0488(19) .0379(17) .0147(16) -.0060(14) .0118(14) C19 .0299(16) .0437(17) .0431(17) -.0031(13) -.0079(14) .0035(14) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .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 C3 O1 C7 117.13(18) C4 O2 C8 117.26(19) C9 O4 H4 109.5 C11 O5 H5 109.5 C12 O6 C10 119.21(17) C13 O7 C18 117.1(2) C17 O8 C19 117.2(2) C6 C1 C2 118.7(2) C6 C1 C9 122.5(2) C2 C1 C9 118.7(2) C3 C2 C1 121.0(2) C3 C2 H2 119.5 C1 C2 H2 119.5 O1 C3 C2 125.6(2) O1 C3 C4 114.8(2) C2 C3 C4 119.6(2) O2 C4 C5 125.4(2) O2 C4 C3 115.4(2) C5 C4 C3 119.2(2) C4 C5 C6 120.5(2) C4 C5 H5A 119.7 C6 C5 H5A 119.7 C1 C6 C5 120.9(2) C1 C6 H6 119.6 C5 C6 H6 119.6 O1 C7 H7A 109.5 O1 C7 H7B 109.5 H7A C7 H7B 109.5 O1 C7 H7C 109.5 H7A C7 H7C 109.5 H7B C7 H7C 109.5 O2 C8 H8A 109.5 O2 C8 H8B 109.5 H8A C8 H8B 109.5 O2 C8 H8C 109.5 H8A C8 H8C 109.5 H8B C8 H8C 109.5 O4 C9 C1 112.49(19) O4 C9 C10 109.19(18) C1 C9 C10 112.22(19) O4 C9 H9 107.6 C1 C9 H9 107.6 C10 C9 H9 107.6 O6 C10 C9 103.73(17) O6 C10 C11 112.67(17) C9 C10 C11 112.66(19) O6 C10 H10 109.2 C9 C10 H10 109.2 C11 C10 H10 109.2 O5 C11 C10 109.38(18) O5 C11 H11A 109.8 C10 C11 H11A 109.8 O5 C11 H11B 109.8 C10 C11 H11B 109.8 H11A C11 H11B 108.2 O6 C12 C17 121.0(2) O6 C12 C13 118.3(2) C17 C12 C13 120.6(2) O7 C13 C12 114.7(2) O7 C13 C14 125.9(2) C12 C13 C14 119.4(2) C15 C14 C13 119.3(2) C15 C14 H14 120.3 C13 C14 H14 120.3 C14 C15 C16 122.1(2) C14 C15 H15 119.0 C16 C15 H15 119.0 C17 C16 C15 118.7(3) C17 C16 H16 120.6 C15 C16 H16 120.6 O8 C17 C12 114.9(2) O8 C17 C16 125.2(2) C12 C17 C16 119.9(2) O7 C18 H18A 109.5 O7 C18 H18B 109.5 H18A C18 H18B 109.5 O7 C18 H18C 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 O8 C19 H19A 109.5 O8 C19 H19B 109.5 H19A C19 H19B 109.5 O8 C19 H19C 109.5 H19A C19 H19C 109.5 H19B C19 H19C 109.5 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 C3 . 1.369(3) ? O1 C7 . 1.429(3) ? O2 C4 . 1.372(3) ? O2 C8 . 1.433(3) ? O4 C9 . 1.436(3) ? O4 H4 . .840 ? O5 C11 . 1.428(3) ? O5 H5 . .840 ? O6 C12 . 1.384(3) ? O6 C10 . 1.451(3) ? O7 C13 . 1.370(3) ? O7 C18 . 1.436(3) ? O8 C17 . 1.370(3) ? O8 C19 . 1.433(3) ? C1 C6 . 1.376(3) ? C1 C2 . 1.404(3) ? C1 C9 . 1.515(3) ? C2 C3 . 1.379(3) ? C2 H2 . .950 ? C3 C4 . 1.414(3) ? C4 C5 . 1.378(3) ? C5 C6 . 1.394(3) ? C5 H5A . .950 ? C6 H6 . .950 ? C7 H7A . .980 ? C7 H7B . .980 ? C7 H7C . .980 ? C8 H8A . .980 ? C8 H8B . .980 ? C8 H8C . .980 ? C9 C10 . 1.528(3) ? C9 H9 . 1.0000 ? C10 C11 . 1.517(3) ? C10 H10 . 1.000 ? C11 H11A . .990 ? C11 H11B . .990 ? C12 C17 . 1.393(3) ? C12 C13 . 1.396(3) ? C13 C14 . 1.391(4) ? C14 C15 . 1.379(4) ? C14 H14 . .950 ? C15 C16 . 1.387(4) ? C15 H15 . .950 ? C16 C17 . 1.391(3) ? C16 H16 . .9500 ? C18 H18A . .980 ? C18 H18B . .980 ? C18 H18C . .980 ? C19 H19A . .980 ? C19 H19B . .980 ? C19 H19C . .980 ? 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 H4 O6 . .84 2.20 2.669(2) 115 O4 H4 O7 . .84 2.24 3.051(2) 163 O5 H5 O4 1_655 .84 1.99 2.807(2) 164 C8 H8B O8 2_666 .98 2.55 3.359(3) 139 C9 H9 O5 . 1.00 2.52 2.940(3) 105 C19 H19B O2 2_766 .98 2.56 3.418(3) 146 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 C6 C1 C2 C3 -.2(3) C9 C1 C2 C3 177.0(2) C7 O1 C3 C2 -2.5(3) C7 O1 C3 C4 176.9(2) C1 C2 C3 O1 180.0(2) C1 C2 C3 C4 .6(3) C8 O2 C4 C5 -7.7(3) C8 O2 C4 C3 173.0(2) O1 C3 C4 O2 -.3(3) C2 C3 C4 O2 179.1(2) O1 C3 C4 C5 -179.7(2) C2 C3 C4 C5 -.2(3) O2 C4 C5 C6 -179.8(2) C3 C4 C5 C6 -.5(3) C2 C1 C6 C5 -.5(3) C9 C1 C6 C5 -177.7(2) C4 C5 C6 C1 .9(4) C6 C1 C9 O4 -26.8(3) C2 C1 C9 O4 156.1(2) C6 C1 C9 C10 96.8(3) C2 C1 C9 C10 -80.3(3) C12 O6 C10 C9 -148.25(19) C12 O6 C10 C11 -26.1(3) O4 C9 C10 O6 54.9(2) C1 C9 C10 O6 -70.5(2) O4 C9 C10 C11 -67.2(2) C1 C9 C10 C11 167.35(19) O6 C10 C11 O5 -178.47(19) C9 C10 C11 O5 -61.5(3) C10 O6 C12 C17 -76.6(3) C10 O6 C12 C13 107.6(2) C18 O7 C13 C12 -176.2(2) C18 O7 C13 C14 4.1(4) O6 C12 C13 O7 -4.4(3) C17 C12 C13 O7 179.7(2) O6 C12 C13 C14 175.3(2) C17 C12 C13 C14 -.5(4) O7 C13 C14 C15 179.4(2) C12 C13 C14 C15 -.3(4) C13 C14 C15 C16 1.0(4) C14 C15 C16 C17 -.7(4) C19 O8 C17 C12 -177.0(2) C19 O8 C17 C16 2.8(3) O6 C12 C17 O8 4.8(3) C13 C12 C17 O8 -179.4(2) O6 C12 C17 C16 -174.9(2) C13 C12 C17 C16 .8(3) C15 C16 C17 O8 -179.9(2) C15 C16 C17 C12 -.2(4) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21132541 2 PubChem 13904326