#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/51/2005149.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_2005149 loop_ _publ_author_name 'Zukerman-Schpector, J.' 'Monteiro, H. J.' _publ_section_title ; Intermediates in the Synthesis of (+)-Grandisol. I ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1767 _journal_page_last 1770 _journal_paper_doi 10.1107/S0108270196004222 _journal_volume 52 _journal_year 1996 _chemical_formula_moiety 'C15 H20 O4 S' _chemical_formula_sum 'C15 H20 O4 S' _chemical_formula_weight 296.381 _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.0040(10) _cell_length_b 10.2730(10) _cell_length_c 14.7190(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 16.79 _cell_measurement_theta_min 9.49 _cell_volume 1512.7(2) _computing_cell_refinement 'CAD4 Software' _computing_data_collection 'CAD4 Software (Enraf-Nonius,1989)' _computing_data_reduction 'CAD4 Software' _computing_molecular_graphics 'ZORTEP (Zsolnai, 1995)' _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_measurement_device 'Enraf-Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0093 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_number 2237 _diffrn_reflns_theta_max 27.98 _diffrn_reflns_theta_min 2.42 _diffrn_standards_decay_% -1.1 _diffrn_standards_interval_time 30 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.224 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.3014 _exptl_crystal_density_meas ? _exptl_crystal_description irregular _exptl_crystal_F_000 632 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.495 _refine_diff_density_min -0.625 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack -0.1(2) _refine_ls_extinction_coef 0.013(4) _refine_ls_extinction_method 'SHELXL93 (Sheldrick, 1993)' _refine_ls_goodness_of_fit_all 1.119 _refine_ls_goodness_of_fit_obs 1.110 _refine_ls_hydrogen_treatment 'refxyz and one common U' _refine_ls_matrix_type full _refine_ls_number_parameters 243 _refine_ls_number_reflns 2211 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.119 _refine_ls_restrained_S_obs 1.110 _refine_ls_R_factor_all 0.1035 _refine_ls_R_factor_obs 0.0681 _refine_ls_shift/esd_max -0.041 _refine_ls_shift/esd_mean 0.002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1120P)^2^+0.4682P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.2031 _refine_ls_wR_factor_obs 0.1613 _reflns_number_observed 1486 _reflns_number_total 2211 _reflns_observed_criterion >2sigma(I) _cod_data_source_file li1145.cif _cod_data_source_block 1 _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.1120P)^2^+0.4682P] where P=(Fo^2^+2Fc^2^)/3' 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^(Fo^2^)+(0.1120P)^2^+0.4682P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2005149 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' 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 S 0.0585(7) 0.0641(7) 0.0496(7) -0.0121(6) -0.0016(6) -0.0035(7) O1 0.079(3) 0.102(3) 0.063(3) 0.002(3) -0.011(2) 0.033(3) O2 0.067(2) 0.099(3) 0.043(2) 0.004(2) -0.013(2) 0.007(2) O3 0.087(3) 0.062(2) 0.091(3) -0.013(2) 0.008(3) 0.012(2) O4 0.078(2) 0.120(4) 0.053(2) -0.022(3) -0.007(2) -0.036(3) C1 0.065(3) 0.064(3) 0.039(2) -0.001(3) 0.001(2) -0.001(2) C2 0.048(2) 0.058(3) 0.031(2) -0.005(2) -0.004(2) 0.003(2) C3 0.050(2) 0.059(3) 0.056(3) 0.004(2) 0.000(2) -0.004(2) C4 0.048(3) 0.079(4) 0.061(3) -0.001(3) 0.012(2) -0.013(3) C5 0.078(4) 0.089(4) 0.053(3) -0.011(4) 0.015(3) 0.005(4) C6 0.078(4) 0.077(4) 0.079(5) -0.001(4) 0.006(4) -0.028(4) C7 0.068(3) 0.071(4) 0.068(4) 0.016(3) -0.004(3) 0.012(3) C8 0.062(3) 0.089(4) 0.061(3) 0.007(3) -0.014(3) 0.012(4) C9 0.106(5) 0.093(5) 0.045(3) 0.004(4) -0.018(3) 0.005(3) C10 0.047(2) 0.081(4) 0.040(2) -0.014(2) -0.003(2) 0.006(3) C11 0.063(3) 0.103(4) 0.044(3) -0.010(3) 0.001(2) 0.004(3) C12 0.076(4) 0.143(7) 0.052(4) -0.017(5) 0.022(3) -0.021(4) C13 0.047(3) 0.126(6) 0.100(6) -0.004(4) 0.013(4) -0.019(5) C14 0.054(3) 0.099(5) 0.095(5) 0.000(3) -0.016(4) 0.013(5) C15 0.060(3) 0.085(4) 0.060(3) -0.009(3) -0.010(3) 0.007(4) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv S -0.17381(13) -.03800(13) -0.83449(10) .0574(4) O1 -0.1200(5) .2141(5) -0.9439(3) .0811(14) O2 .0309(4) .0240(5) -0.6346(3) .0700(11) O3 -0.1492(5) -0.1467(4) -0.7786(4) .0802(13) O4 -0.2147(5) -.0615(5) -0.9270(3) .0840(15) C1 -.0248(6) .1659(5) -0.9091(4) .0559(12) C2 -.0277(4) .0623(5) -0.8338(3) .0457(10) C3 .1096(5) -.0065(5) -0.8414(4) .0550(12) C4 .1985(6) .1091(7) -0.8668(4) .0628(15) C5 .1193(7) .1920(8) -0.9312(5) .073(2) C6 .1114(8) -0.1054(8) -0.9179(6) .078(2) C7 .1578(7) -.0745(6) -0.7538(5) .069(2) C8 .1609(6) .0024(7) -0.6666(5) .071(2) C9 .0276(10) .0670(9) -0.5439(4) .081(2) C10 -0.2950(5) .0597(6) -0.7811(3) .0561(13) C11 -0.3028(6) .0605(8) -0.6864(4) .070(2) C12 -0.3981(8) .1339(10) -0.6457(5) .090(3) C13 -0.4843(7) .2095(9) -0.6935(6) .091(2) C14 -0.4762(7) .2088(8) -0.7876(6) .082(2) C15 -0.3822(6) .1343(7) -0.8319(5) .0681(15) H2 -.022(7) .111(7) -0.778(5) .084(5) H4 .225(7) .165(7) -0.812(5) .084(5) H'4 .283(8) .077(7) -0.887(5) .084(5) H5 .132(7) .158(7) -0.988(5) .084(5) H'5 .131(7) .286(8) -0.939(6) .084(5) H6 .060(7) -0.171(8) -0.897(5) .084(5) H'6 .216(7) -0.132(7) -0.933(5) .084(5) H"6 .094(8) -.062(7) -0.967(6) .084(5) H7 .111(7) -0.139(8) -0.742(5) .084(5) H'7 .250(7) -0.112(7) -0.765(5) .084(5) H8 .194(7) .080(7) -0.667(6) .084(5) H'8 .208(7) -.049(7) -0.624(5) .084(5) H9 -.070(8) .088(7) -0.527(5) .084(5) H'9 .086(7) .136(8) -0.531(5) .084(5) H"9 .056(8) .003(8) -0.519(6) .084(5) H11 -0.244(7) -.019(7) -0.652(5) .084(5) H12 -0.399(7) .150(7) -0.594(5) .084(5) H13 -0.562(7) .265(6) -0.667(5) .084(5) H14 -0.529(8) .252(7) -0.832(5) .084(5) H15 -0.369(7) .140(7) -0.894(5) .084(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' 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 O3 S O4 117.9(3) yes O3 S C10 108.2(3) yes O4 S C10 108.8(3) yes O3 S C2 108.1(2) yes O4 S C2 109.5(3) yes C10 S C2 103.4(2) yes C8 O2 C9 113.0(6) yes O1 C1 C5 127.0(6) yes O1 C1 C2 125.7(5) yes C5 C1 C2 107.3(5) yes C1 C2 C3 104.3(4) yes C1 C2 S 114.2(3) yes C3 C2 S 117.5(3) yes C6 C3 C4 109.4(5) yes C6 C3 C7 108.2(5) yes C4 C3 C7 111.9(5) yes C6 C3 C2 111.7(5) yes C4 C3 C2 100.3(4) yes C7 C3 C2 115.0(5) yes C5 C4 C3 106.7(5) yes C4 C5 C1 105.7(5) yes C8 C7 C3 118.8(5) yes O2 C8 C7 110.5(5) yes C15 C10 C11 120.1(6) yes C15 C10 S 120.7(5) yes C11 C10 S 119.2(5) yes C12 C11 C10 118.9(7) yes C11 C12 C13 122.4(7) yes C12 C13 C14 118.5(7) yes C15 C14 C13 121.1(7) yes C14 C15 C10 118.9(7) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S O3 1.409(5) yes S O4 1.442(4) yes S C10 1.759(6) yes S C2 1.788(4) yes O1 C1 1.189(7) yes O2 C8 1.400(8) yes O2 C9 1.407(8) yes C1 C5 1.502(9) yes C1 C2 1.537(7) yes C2 C3 1.548(7) yes C3 C6 1.516(9) yes C3 C4 1.530(8) yes C3 C7 1.544(8) yes C4 C5 1.500(10) yes C7 C8 1.507(10) yes C10 C15 1.381(8) yes C10 C11 1.397(7) yes C11 C12 1.355(11) yes C12 C13 1.357(12) yes C13 C14 1.387(11) yes C14 C15 1.377(10) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 10913476