#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/03/2010378.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_2010378 loop_ _publ_author_name 'Hellier, Desmond G.' 'Motevalli, Majid' _publ_section_title ; Two Isomeric Sulfites of 10\b-Pinane-2,3\a-diol ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 116 _journal_page_last 119 _journal_paper_doi 10.1107/S0108270194007183 _journal_volume 51 _journal_year 1995 _chemical_formula_sum 'C10 H16 O3 S' _chemical_formula_weight 216.29 _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' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.1760(10) _cell_length_b 11.969(2) _cell_length_c 12.621(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 13 _cell_measurement_theta_min 11 _cell_volume 1084.0(3) _computing_cell_refinement CAD4/PC _computing_data_collection 'CAD4/PC software (Enraf-Nonius, 1989)' _computing_data_reduction CAD4 _computing_molecular_graphics 'PLUTON (Spek, 1993)' _computing_publication_material SHELXL-93 _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Enraf-Nonius CAD4 4-circle' _diffrn_measurement_method 2\q/\w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0136 _diffrn_reflns_av_sigmaI/netI 0.1969 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -2 _diffrn_reflns_number 935 _diffrn_reflns_theta_max 22.97 _diffrn_reflns_theta_min 2.34 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.278 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_correction_T_min 0.987 _exptl_absorpt_correction_type empirical _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_meas 1.4 _exptl_crystal_density_method flotation _exptl_crystal_description 'transparent rhombic' _exptl_crystal_F_000 464 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.248 _refine_diff_density_min -0.256 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 0.947 _refine_ls_goodness_of_fit_obs 1.182 _refine_ls_hydrogen_treatment ' H atoms: calculated using AFIX in SHELXL92 (Sheldrick, 1992)' _refine_ls_matrix_type full _refine_ls_number_parameters 138 _refine_ls_number_reflns 897 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.947 _refine_ls_restrained_S_obs 1.182 _refine_ls_R_factor_all 0.1130 _refine_ls_R_factor_obs 0.0477 _refine_ls_shift/esd_max -0.008 _refine_ls_shift/esd_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0656P)^2^+0.0000P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1163 _refine_ls_wR_factor_obs 0.1046 _reflns_number_observed 531 _reflns_number_total 897 _reflns_observed_criterion >2sigma(I) _cod_data_source_file hu1093.cif _cod_data_source_block 2 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0656P)^2^+0.0000P] 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^)+(0.0656P)^2^+0.0000P] 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 2010378 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 S1 0.0561(14) 0.0567(12) 0.0498(12) 0.0019(12) 0.0046(12) 0.0144(11) O1 0.062(4) 0.060(3) 0.043(3) -0.009(3) 0.006(3) -0.007(3) O2 0.049(3) 0.042(3) 0.059(3) 0.004(2) 0.007(3) 0.006(2) O3 0.046(3) 0.089(4) 0.088(4) -0.007(3) 0.010(3) 0.005(4) C1 0.026(4) 0.036(4) 0.050(4) -0.001(4) -0.005(4) 0.003(4) C2 0.030(4) 0.035(4) 0.047(5) -0.004(4) 0.007(4) -0.014(4) C3 0.038(4) 0.052(5) 0.038(4) -0.010(5) 0.003(4) 0.002(4) C4 0.067(5) 0.049(4) 0.050(5) 0.009(5) 0.003(5) -0.010(4) C5 0.030(5) 0.060(5) 0.045(5) 0.015(4) -0.001(4) 0.013(4) C6 0.039(4) 0.063(5) 0.047(5) -0.004(4) -0.007(4) 0.000(4) C7 0.045(5) 0.079(7) 0.078(6) 0.020(5) -0.003(5) 0.012(5) C8 0.051(5) 0.048(5) 0.042(5) -0.008(5) 0.009(4) 0.002(4) C9 0.070(6) 0.060(5) 0.047(5) 0.001(5) 0.008(4) 0.006(4) C10 0.084(7) 0.074(6) 0.037(4) 0.006(6) 0.003(5) -0.003(4) 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 _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol S1 -0.0198(3) 0.0325(2) 0.01537(15) 0.0542(6) Uani d . 1 . S O1 0.0608(6) 0.1581(4) 0.0134(4) 0.0553(15) Uani d . 1 . O O2 0.0794(6) -0.0027(4) -0.0944(4) 0.0504(14) Uani d . 1 . O O3 -0.2179(7) 0.0353(5) -0.0021(4) 0.074(2) Uani d . 1 . O C1 0.1766(9) 0.0891(6) -0.1517(5) 0.038(2) Uani d . 1 . C C2 0.1073(9) 0.0882(5) -0.2654(5) 0.038(2) Uani d . 1 . C H2 0.1482(9) 0.0248(5) -0.3086(5) 0.08(3) Uiso calc R 1 . H C3 0.1199(11) 0.1962(6) -0.0913(5) 0.043(2) Uani d . 1 . C H3 0.2329(11) 0.2411(6) -0.0816(5) 0.06(2) Uiso calc R 1 . H C4 -0.0237(11) 0.2698(6) -0.1462(5) 0.055(2) Uani d . 1 . C H4A -0.1403(11) 0.2658(6) -0.1075(5) 0.11(3) Uiso calc R 1 . H H4B 0.0187(11) 0.3467(6) -0.1443(5) 0.11(3) Uiso calc R 1 . H C5 -0.0578(9) 0.2359(6) -0.2608(6) 0.045(2) Uani d . 1 . C H5 -0.1429(9) 0.2846(6) -0.3003(6) 0.08(3) Uiso calc R 1 . H C6 -0.1047(10) 0.1110(6) -0.2648(6) 0.049(2) Uani d . 1 . C H6A -0.1681(10) 0.0880(6) -0.3291(6) 0.050(14) Uiso calc R 1 . H H6B -0.1684(10) 0.0834(6) -0.2023(6) 0.050(14) Uiso calc R 1 . H C7 0.3830(10) 0.0619(7) -0.1418(6) 0.067(3) Uani d . 1 . C H7A 0.4545(11) 0.117(2) -0.180(3) 0.060(13) Uiso calc R 1 . H H7B 0.4065(14) -0.0108(16) -0.171(3) 0.060(13) Uiso calc R 1 . H H7C 0.4181(16) 0.063(3) -0.0684(6) 0.060(13) Uiso calc R 1 . H C8 0.1265(11) 0.2066(6) -0.3187(5) 0.047(2) Uani d . 1 . C C9 0.2974(11) 0.2801(6) -0.3010(6) 0.059(2) Uani d . 1 . C H9A 0.316(3) 0.291(2) -0.2264(6) 0.042(11) Uiso calc R 1 . H H9B 0.279(2) 0.3512(12) -0.335(2) 0.042(11) Uiso calc R 1 . H H9C 0.4051(14) 0.2444(15) -0.331(3) 0.042(11) Uiso calc R 1 . H C10 0.1021(13) 0.1979(7) -0.4388(5) 0.065(3) Uani d . 1 . C H10A -0.010(3) 0.157(3) -0.4544(5) 0.070(14) Uiso calc R 1 . H H10B 0.207(3) 0.159(3) -0.4688(6) 0.070(14) Uiso calc R 1 . H H10C 0.094(6) 0.2715(7) -0.4687(6) 0.070(14) Uiso calc R 1 . H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 S1 O1 109.3(3) yes O3 S1 O2 108.1(3) yes O1 S1 O2 94.1(3) yes C3 O1 S1 114.2(4) yes C1 O2 S1 115.6(4) yes O2 C1 C2 107.5(5) yes O2 C1 C7 104.9(5) yes C2 C1 C7 113.3(6) yes O2 C1 C3 104.4(5) yes C2 C1 C3 112.7(6) yes C7 C1 C3 113.1(6) yes C1 C2 C6 108.5(6) yes C1 C2 C8 111.6(5) yes C6 C2 C8 85.9(6) yes C1 C2 H2 115.7(4) ? C6 C2 H2 115.7(4) ? C8 C2 H2 115.7(4) ? O1 C3 C4 113.3(6) yes O1 C3 C1 105.3(5) yes C4 C3 C1 115.7(5) yes O1 C3 H3 107.4(3) ? C4 C3 H3 107.4(4) ? C1 C3 H3 107.4(4) ? C5 C4 C3 112.8(6) yes C5 C4 H4A 109.0(4) ? C3 C4 H4A 109.0(4) ? C5 C4 H4B 109.0(4) ? C3 C4 H4B 109.0(4) ? H4A C4 H4B 107.8 ? C4 C5 C6 109.1(6) yes C4 C5 C8 111.8(6) yes C6 C5 C8 87.2(6) yes C4 C5 H5 115.2(4) ? C6 C5 H5 115.2(4) ? C8 C5 H5 115.2(4) ? C5 C6 C2 87.5(5) yes C5 C6 H6A 114.1(4) ? C2 C6 H6A 114.1(4) ? C5 C6 H6B 114.1(4) ? C2 C6 H6B 114.1(4) ? H6A C6 H6B 111.3 ? C1 C7 H7A 109.5(4) ? C1 C7 H7B 109.5(4) ? H7A C7 H7B 109.5 ? C1 C7 H7C 109.5(4) ? H7A C7 H7C 109.5 ? H7B C7 H7C 109.5 ? C9 C8 C10 106.0(6) ? C9 C8 C5 119.1(6) ? C10 C8 C5 112.6(6) ? C9 C8 C2 121.8(6) ? C10 C8 C2 110.6(6) ? C5 C8 C2 85.9(5) ? C8 C9 H9A 109.5(4) ? C8 C9 H9B 109.5(4) ? H9A C9 H9B 109.5 ? C8 C9 H9C 109.5(4) ? H9A C9 H9C 109.5 ? H9B C9 H9C 109.5 ? C8 C10 H10A 109.5(5) ? C8 C10 H10B 109.5(5) ? H10A C10 H10B 109.5 ? C8 C10 H10C 109.5(4) ? H10A C10 H10C 109.5 ? H10B C10 H10C 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 S1 O3 . 1.439(5) yes S1 O1 . 1.612(5) yes S1 O2 . 1.614(5) yes O1 C3 . 1.460(8) yes O2 C1 . 1.489(7) yes C1 C2 . 1.518(8) yes C1 C7 . 1.522(9) yes C1 C3 . 1.546(9) yes C2 C6 . 1.545(9) yes C2 C8 . 1.574(9) yes C2 H2 . 0.98 ? C3 C4 . 1.523(9) yes C3 H3 . 0.98 ? C4 C5 . 1.522(9) yes C4 H4A . 0.97 ? C4 H4B . 0.97 ? C5 C6 . 1.534(10) yes C5 C8 . 1.551(10) yes C5 H5 . 0.98 ? C6 H6A . 0.97 ? C6 H6B . 0.97 ? C7 H7A . 0.96 ? C7 H7B . 0.96 ? C7 H7C . 0.96 ? C8 C9 . 1.526(10) yes C8 C10 . 1.530(9) yes C9 H9A . 0.96 ? C9 H9B . 0.96 ? C9 H9C . 0.96 ? C10 H10A . 0.96 ? C10 H10B . 0.96 ? C10 H10C . 0.96 ? 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 O3 S1 O1 C3 -90.4(5) O2 S1 O1 C3 20.4(5) O3 S1 O2 C1 106.0(5) O1 S1 O2 C1 -5.8(4) S1 O2 C1 C2 -128.8(5) S1 O2 C1 C7 110.4(5) S1 O2 C1 C3 -8.9(6) O2 C1 C2 C6 61.7(7) C7 C1 C2 C6 177.2(6) C3 C1 C2 C6 -52.7(7) O2 C1 C2 C8 154.7(5) C7 C1 C2 C8 -89.8(7) C3 C1 C2 C8 40.2(8) S1 O1 C3 C4 99.8(6) S1 O1 C3 C1 -27.6(7) O2 C1 C3 O1 21.1(7) C2 C1 C3 O1 137.4(5) C7 C1 C3 O1 -92.4(7) O2 C1 C3 C4 -104.8(6) C2 C1 C3 C4 11.5(8) C7 C1 C3 C4 141.7(7) O1 C3 C4 C5 -132.9(6) C1 C3 C4 C5 -11.2(9) C3 C4 C5 C6 52.8(8) C3 C4 C5 C8 -41.9(8) C4 C5 C6 C2 -84.3(6) C8 C5 C6 C2 27.7(5) C1 C2 C6 C5 84.2(6) C8 C2 C6 C5 -27.3(5) C4 C5 C8 C9 -42.2(9) C6 C5 C8 C9 -151.6(7) C4 C5 C8 C10 -167.1(6) C6 C5 C8 C10 83.4(7) C4 C5 C8 C2 82.2(6) C6 C5 C8 C2 -27.2(5) C1 C2 C8 C9 40.7(9) C6 C2 C8 C9 148.9(7) C1 C2 C8 C10 166.1(6) C6 C2 C8 C10 -85.6(7) C1 C2 C8 C5 -81.3(6) C6 C2 C8 C5 27.0(5) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21187480 2 PubChem 139057469