#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/51/2005107.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_2005107 loop_ _publ_author_name 'Mattern, G.' 'Weckert, E.' 'Youssef, D.' 'Frahm, A. W.' _publ_section_title ; Absolute Configuration of Chlorojanerin, a Chlorine-Containing Guaianolide from Centaurea scoparia ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1791 _journal_page_last 1793 _journal_paper_doi 10.1107/S0108270196000741 _journal_volume 52 _journal_year 1996 _chemical_formula_iupac 'C19 H23 Cl1 O7' _chemical_formula_sum 'C19 H23 Cl O7' _chemical_formula_weight 398.84 _chemical_name_systematic ; (1R,3S,4R,5S,6S,7R,8S)-4-chloromethyl-3,4-diyhdroxy- 8-(4-hydroxymethacrylate)-1H,5H,6H,7H-guaia-10(14),11(13)-dien-6,12-olide, ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _cell_angle_alpha 90.0 _cell_angle_beta 103.21(4) _cell_angle_gamma 90.0 _cell_formula_units_Z 2 _cell_length_a 8.193(5) _cell_length_b 10.546(6) _cell_length_c 11.092(6) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 16.5 _cell_measurement_theta_min 3 _cell_volume 933.0(9) _computing_cell_refinement 'Syntex R3 software' _computing_data_collection 'Syntex R3 software' _computing_data_reduction 'CRYSTALS (Watkin, Carruthers & Betteridge, 1985)' _computing_molecular_graphics 'CRYSTAN88 (Burzlaff & Rothammel, 1988)' _computing_publication_material 'CRYSTALS and local software' _computing_structure_refinement CRYSTALS _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 293 _diffrn_measurement_device 'Syntex R3 four-circle' _diffrn_measurement_method \q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 7467 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 2 _diffrn_standards_decay_% none _diffrn_standards_interval_count 200 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.24 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 420 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.41 _refine_diff_density_min -0.32 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack -0.01(5) _refine_ls_extinction_coef 58E1(2) _refine_ls_extinction_method 'Larson (1970)' _refine_ls_goodness_of_fit_all 2.27 _refine_ls_goodness_of_fit_obs 2.34 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 338 _refine_ls_number_reflns 4026 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.0 _refine_ls_restrained_S_obs 0.0 _refine_ls_R_factor_all 0.0381 _refine_ls_R_factor_obs 0.0354 _refine_ls_shift/esd_max 0.01 _refine_ls_shift/esd_mean 0.0014 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0003F^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0367 _refine_ls_wR_factor_obs 0.0366 _reflns_number_observed 4026 _reflns_number_total 4275 _reflns_observed_criterion refl_observed_if_F>_1.5_\s(F) _cod_data_source_file cf1061.cif _cod_data_source_block chlorojanerin _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(F) + 0.0003F^2^]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(F) + 0.0003F^2^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 933.027 _cod_original_sg_symbol_Hall 'P 2y1' _cod_original_sg_symbol_H-M 'P 21' _cod_original_formula_sum 'C19 H23 Cl1 O7' _cod_database_code 2005107 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' 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 Cl1 0.0518(3) 0.0727(4) 0.0297(2) -0.0083(3) 0.0040(2) -0.0025(3) O1 0.0418(9) 0.0313(8) 0.0442(8) -0.0083(6) 0.0010(7) 0.0028(7) O2 0.0473(9) 0.0390(9) 0.0450(10) 0.0003(7) 0.0031(7) 0.0068(7) O3 0.0407(8) 0.0532(9) 0.0314(7) -0.0028(7) 0.0071(6) -0.0163(7) O4 0.0550(10) 0.0930(10) 0.0520(10) 0.0000(10) 0.0137(8) -0.0370(10) O5 0.0508(9) 0.0369(8) 0.0280(7) -0.0012(6) 0.0014(6) 0.0025(7) O6 0.0930(10) 0.0400(10) 0.0480(10) -0.0041(8) -0.0007(9) 0.0069(9) O7 0.0490(10) 0.0580(10) 0.0520(10) -0.0013(9) 0.0068(8) 0.0056(8) C1 0.0400(10) 0.0300(10) 0.0340(10) -0.0014(8) 0.0072(8) -0.0043(9) C2 0.0320(10) 0.0580(10) 0.0380(10) -0.0020(10) 0.0056(8) -0.0060(10) C3 0.0318(9) 0.0320(10) 0.0336(9) -0.0045(9) 0.0009(8) -0.0037(9) C4 0.0330(10) 0.0310(10) 0.0296(9) -0.0049(8) 0.0028(7) -0.0024(9) C5 0.0294(9) 0.0310(10) 0.0295(8) -0.0018(8) 0.0018(7) 0.0028(9) C6 0.0300(10) 0.0330(10) 0.0288(9) 0.0000(8) 0.0064(8) -0.0036(9) C7 0.0350(10) 0.0290(10) 0.0300(10) -0.0016(8) 0.0016(8) -0.0005(9) C8 0.0420(10) 0.0330(10) 0.0265(9) -0.0001(8) 0.0016(8) 0.0037(9) C9 0.0390(10) 0.0450(10) 0.0310(10) 0.0001(9) 0.0087(9) 0.0040(10) C10 0.0360(10) 0.0430(10) 0.0325(9) 0.0012(9) 0.0078(8) -0.0023(9) C11 0.0340(10) 0.0400(10) 0.0400(10) -0.0067(9) 0.0031(9) -0.0030(9) C12 0.0360(10) 0.0470(10) 0.0450(10) -0.0050(10) 0.0060(10) -0.0110(10) C13 0.0420(10) 0.079(2) 0.0420(10) -0.0070(10) 0.0000(10) -0.0120(10) C14 0.087(2) 0.052(2) 0.0390(10) 0.0060(10) 0.0150(10) -0.0060(10) C15 0.0380(10) 0.0490(10) 0.0269(9) -0.0039(9) 0.0029(8) -0.0060(10) C16 0.0400(10) 0.0410(10) 0.0340(10) -0.0041(9) 0.0072(9) 0.0010(10) C17 0.0360(10) 0.0550(10) 0.0310(10) -0.0020(10) 0.0055(9) -0.0070(10) C18 0.0420(10) 0.062(2) 0.0400(10) 0.0130(10) 0.0000(10) -0.0040(10) C19 0.061(2) 0.082(2) 0.0360(10) -0.0120(10) 0.0090(10) -0.013(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_thermal_displace_type Cl1 0.95129(7) 0.2081(3) 0.81748(5) 0.0523 Uani O1 0.9264(2) 0.3701(3) 0.5916(1) 0.0405 Uani O2 1.1501(2) 0.0766(3) 0.6154(2) 0.0450 Uani O3 0.6598(2) 0.0351(3) 0.4630(1) 0.0419 Uani O4 0.4233(2) -0.0736(3) 0.4359(2) 0.0664 Uani O5 0.6930(2) 0.0420(3) 0.0450(1) 0.0398 Uani O6 0.6875(3) -0.1668(3) 0.0061(2) 0.0630 Uani O7 0.3525(2) 0.1073(3) -0.1437(2) 0.0538 Uani C1 0.9672(3) 0.2648(3) 0.3630(2) 0.0349 Uani C2 1.1352(3) 0.2194(4) 0.4450(2) 0.0431 Uani C3 1.1099(2) 0.2027(3) 0.5760(2) 0.0335 Uani C4 0.9249(2) 0.2365(3) 0.5689(2) 0.0319 Uani C5 0.8332(2) 0.2162(3) 0.4310(2) 0.0308 Uani C6 0.7757(2) 0.0830(3) 0.3909(2) 0.0307 Uani C7 0.6767(2) 0.0779(3) 0.2543(2) 0.0323 Uani C8 0.7858(3) 0.0252(3) 0.1721(2) 0.0348 Uani C9 0.9517(3) 0.0955(3) 0.1889(2) 0.0382 Uani C10 0.9463(2) 0.2326(3) 0.2264(2) 0.0372 Uani C11 0.5217(3) 0.0053(3) 0.2597(2) 0.0389 Uani C12 0.5239(3) -0.0181(3) 0.3910(2) 0.0432 Uani C13 0.3931(3) -0.0314(4) 0.1717(3) 0.0559 Uani C14 0.9289(4) 0.3240(4) 0.1434(2) 0.0592 Uani C15 0.8465(3) 0.1684(3) 0.6614(2) 0.0387 Uani C16 0.6591(3) -0.0594(3) -0.0284(2) 0.0385 Uani C17 0.5835(3) -0.0219(3) -0.1582(2) 0.0410 Uani C18 0.5079(3) 0.1068(4) -0.1825(2) 0.0495 Uani C19 0.5887(4) -0.1051(4) -0.2466(2) 0.0600 Uani H1 0.832(4) 0.406(3) 0.563(3) 0.10(1) Uiso H2 1.191(4) 0.081(3) 0.688(3) 0.07(1) Uiso H3 0.344(4) 0.177(3) -0.101(3) 0.069(9) Uiso H11 0.969(2) 0.353(2) 0.370(2) 0.029(5) Uiso H21 1.229(3) 0.279(2) 0.442(2) 0.049(7) Uiso H22 1.171(3) 0.139(3) 0.418(2) 0.055(7) Uiso H31 1.175(3) 0.259(2) 0.629(2) 0.034(6) Uiso H51 0.732(3) 0.267(2) 0.414(2) 0.033(6) Uiso H61 0.868(3) 0.022(2) 0.405(2) 0.037(6) Uiso H71 0.651(3) 0.157(2) 0.231(2) 0.031(5) Uiso H81 0.809(2) -0.062(2) 0.184(2) 0.024(5) Uiso H91 1.033(3) 0.052(2) 0.252(2) 0.038(6) Uiso H92 0.990(3) 0.091(2) 0.109(2) 0.041(6) Uiso H131 0.377(3) -0.007(2) 0.091(3) 0.058(8) Uiso H132 0.286(4) -0.070(3) 0.190(3) 0.083(9) Uiso H141 0.922(3) 0.415(3) 0.165(2) 0.055(7) Uiso H142 0.920(3) 0.302(3) 0.060(3) 0.069(8) Uiso H151 0.852(3) 0.083(2) 0.656(2) 0.040(6) Uiso H152 0.723(3) 0.195(2) 0.651(2) 0.042(6) Uiso H181 0.489(3) 0.130(2) -0.269(2) 0.050(7) Uiso H182 0.588(3) 0.173(2) -0.136(2) 0.059(7) Uiso H191 0.646(3) -0.191(3) -0.223(3) 0.066(9) Uiso H192 0.547(3) -0.082(3) -0.337(2) 0.061(8) Uiso loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C .002 .002 International_Tables_Vol_IV_Table_2.3.1 H .000 .000 International_Tables_Vol_IV_Table_2.3.1 CL .132 .159 International_Tables_Vol_IV_Table_2.3.1 N .004 .003 International_Tables_Vol_IV_Table_2.3.1 O .008 .006 International_Tables_Vol_IV_Table_2.3.1 S .110 .124 International_Tables_Vol_IV_Table_2.3.1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 0 0 0 0 4 0 6 0 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C12 O3 C6 112.0(2) yes C16 O5 C8 119.0(2) no C5 C1 C2 104.2(2) yes C10 C1 C2 113.6(2) no C10 C1 C5 118.5(2) yes C3 C2 C1 107.5(2) yes C2 C3 O2 109.3(2) no C4 C3 O2 113.0(2) no C4 C3 C2 105.7(2) yes C3 C4 O1 104.5(2) no C5 C4 O1 106.9(2) no C5 C4 C3 105.40(10) yes C15 C4 O1 109.7(2) no C15 C4 C3 114.9(2) no C15 C4 C5 114.6(2) no C4 C5 C1 101.30(10) yes C6 C5 C1 111.7(2) yes C6 C5 C4 117.6(2) no C5 C6 O3 110.9(2) no C7 C6 O3 105.20(10) yes C7 C6 C5 112.2(2) yes C8 C7 C6 110.6(2) yes C11 C7 C6 103.7(2) yes C11 C7 C8 117.3(2) no C7 C8 O5 106.8(2) no C9 C8 O5 108.3(2) no C9 C8 C7 112.3(2) yes C10 C9 C8 114.8(2) yes C9 C10 C1 119.0(2) yes C14 C10 C1 120.0(2) no C14 C10 C9 120.9(2) no C12 C11 C7 107.9(2) yes C13 C11 C7 131.4(2) no C13 C11 C12 120.6(2) no O4 C12 O3 120.8(2) no C11 C12 O3 109.9(2) yes C11 C12 O4 129.3(2) no C4 C15 Cl1 111.10(10) no O6 C16 O5 124.3(2) no C17 C16 O5 111.1(2) no C17 C16 O6 124.6(2) no C18 C17 C16 118.8(2) no C19 C17 C16 117.7(2) no C19 C17 C18 123.5(2) no C17 C18 O7 108.1(2) no H1 O1 C4 114.(2) no H2 O2 C3 106.(2) no H3 O7 C18 110.4(19) no H11 C1 C2 105.5(12) no H11 C1 C5 106.8(12) no H11 C1 C10 107.4(12) no H21 C2 C1 112.0(14) no H21 C2 C3 112.2(14) no H22 C2 C1 112.4(15) no H22 C2 C3 108.2(16) no H22 C2 H21 105.(2) no H31 C3 O2 110.7(13) no H31 C3 C2 110.4(13) no H31 C3 C4 107.7(13) no H51 C5 C1 112.6(12) no H51 C5 C4 108.4(12) no H51 C5 C6 105.3(12) no H61 C6 O3 104.9(13) no H61 C6 C5 112.8(13) no H61 C6 C7 110.3(12) no H71 C7 C6 106.8(13) no H71 C7 C8 107.5(13) no H71 C7 C11 110.5(13) no H81 C8 O5 107.1(11) no H81 C8 C7 113.9(12) no H81 C8 C9 108.1(11) no H91 C9 C8 107.9(13) no H91 C9 C10 108.3(13) no H92 C9 C8 108.6(12) no H92 C9 C10 108.9(13) no H92 C9 H91 108.3(18) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C15 1.797(2) no O1 C4 1.430(2) no O2 C3 1.415(3) no O3 C6 1.464(2) yes O3 C12 1.336(2) yes O4 C12 1.207(3) no O5 C8 1.452(2) no O5 C16 1.334(3) no O6 C16 1.201(3) no O7 C18 1.434(3) no C1 C2 1.542(3) yes C1 C5 1.554(3) yes C1 C10 1.524(3) yes C2 C3 1.524(3) yes C3 C4 1.541(3) yes C4 C5 1.557(2) yes C4 C15 1.511(3) no C5 C6 1.516(3) yes C6 C7 1.548(3) yes C7 C8 1.520(3) yes C7 C11 1.496(3) yes C8 C9 1.522(3) yes C9 C10 1.508(3) yes C10 C14 1.318(3) no C11 C12 1.474(3) no C11 C13 1.320(3) no C16 C17 1.485(3) no C17 C18 1.491(3) no C17 C19 1.323(3) no O1 H1 0.85(4) no O2 H2 0.80(3) no O7 H3 0.88(3) no C1 H11 0.93(2) no C2 H21 1.00(2) no C2 H22 0.97(3) no C3 H31 0.92(2) no C5 H51 0.97(2) no C6 H61 0.98(2) no C7 H71 0.88(2) no C8 H81 0.95(2) no C9 H91 0.97(2) no C9 H92 1.01(2) no C13 H131 0.91(3) no C13 H132 1.03(3) no C14 H141 0.99(3) no C14 H142 0.94(3) no C15 H151 0.90(2) no C15 H152 1.03(2) no C18 H181 0.97(3) no C18 H182 1.01(3) no C19 H191 1.02(3) no C19 H192 1.01(3) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 182408