#------------------------------------------------------------------------------ #$Date: 2017-10-13 01:08:28 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201955 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/83/2008399.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_2008399 loop_ _publ_author_name 'Degen, Alexander' 'Bolte, Michael' _publ_section_title ; (--)-3-p-Menthyl tosylate ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first IUC9900024 _journal_paper_doi 10.1107/S0108270199099667 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C17 H26 O3 S' _chemical_formula_weight 310.44 _chemical_name_systematic ; toluene-4-sulfonic acid 2-isopropyl-5-methyl-cyclohexyl ester ; _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 5.842(2) _cell_length_b 16.593(5) _cell_length_c 17.561(7) _cell_measurement_reflns_used 512 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 50 _cell_measurement_theta_min 1 _cell_volume 1702.3(10) _computing_cell_refinement SMART _computing_data_collection 'SMART (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 173(2) _diffrn_measurement_device 'Siemens CCD three-circle' _diffrn_measurement_method \w _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 0.021 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 20527 _diffrn_reflns_theta_max 31.08 _diffrn_reflns_theta_min 1.69 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 600 _diffrn_standards_number 123 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_T_max 0.954 _exptl_absorpt_correction_T_min 0.924 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick,1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.211 _exptl_crystal_description block _exptl_crystal_F_000 672 _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.192 _refine_diff_density_min -0.259 _refine_ls_abs_structure_Flack 0.00(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.055 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 191 _refine_ls_number_reflns 4615 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.055 _refine_ls_restrained_S_obs 1.054 _refine_ls_R_factor_all 0.039 _refine_ls_R_factor_gt 0.031 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0460P)^2^+0.2000P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.081 _reflns_number_gt 4145 _reflns_number_total 4615 _reflns_observed_criterion >2sigma(I) _cod_data_source_file qa0096.cif _cod_data_source_block ad1 _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: '_exptl_absorpt_correction_type' value 'Empirical' changed to 'empirical' 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^)+(0.0460P)^2^+0.2000P] 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^)+(0.0460P)^2^+0.2000P] 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 2008399 _cod_database_fobs_code 2008399 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -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 S1 0.02796(15) 0.02513(13) 0.03070(15) 0.00455(11) 0.00173(13) -0.00121(12) O11 0.0488(6) 0.0313(5) 0.0326(5) 0.0042(4) -0.0033(5) -0.0070(4) O12 0.0308(5) 0.0425(5) 0.0464(6) 0.0102(4) 0.0080(5) 0.0030(5) O1 0.0229(4) 0.0247(4) 0.0331(5) 0.0003(3) 0.0026(4) 0.0011(3) C1 0.0217(5) 0.0226(5) 0.0282(6) 0.0011(4) 0.0032(5) 0.0026(5) C2 0.0309(6) 0.0243(5) 0.0252(6) 0.0007(4) 0.0023(5) 0.0007(5) C21 0.0434(8) 0.0321(7) 0.0285(7) 0.0055(6) -0.0012(6) -0.0008(5) C22 0.0616(11) 0.0407(8) 0.0367(8) 0.0055(8) -0.0087(8) -0.0108(6) C23 0.0653(12) 0.0594(10) 0.0315(8) 0.0012(9) 0.0071(8) 0.0107(7) C3 0.0379(7) 0.0336(6) 0.0339(7) 0.0107(6) 0.0042(7) -0.0003(5) C4 0.0361(7) 0.0300(6) 0.0382(7) 0.0068(5) -0.0010(6) 0.0034(5) C5 0.0275(7) 0.0283(6) 0.0345(7) -0.0017(5) -0.0010(5) 0.0054(5) C51 0.0450(9) 0.0411(8) 0.0382(8) 0.0048(7) -0.0102(7) 0.0023(6) C6 0.0313(7) 0.0276(6) 0.0261(6) 0.0015(5) 0.0007(5) 0.0004(5) C11 0.0269(6) 0.0207(5) 0.0311(6) 0.0021(5) -0.0018(5) 0.0010(4) C12 0.0294(7) 0.0308(6) 0.0384(7) -0.0037(5) -0.0066(6) -0.0010(5) C13 0.0410(8) 0.0374(7) 0.0323(7) 0.0000(6) -0.0106(6) -0.0023(5) C14 0.0433(8) 0.0262(6) 0.0335(7) 0.0063(6) 0.0015(6) 0.0014(5) C141 0.0646(12) 0.0426(8) 0.0388(9) 0.0072(8) 0.0087(8) 0.0071(7) C15 0.0285(7) 0.0284(6) 0.0435(8) -0.0019(5) 0.0002(6) 0.0043(5) C16 0.0275(7) 0.0268(6) 0.0364(7) 0.0000(5) -0.0068(5) 0.0020(5) 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 0.21308(6) 0.089462(18) 0.230240(19) 0.02793(8) Uani d . 1 . S O11 0.0713(2) 0.05401(6) 0.17293(6) 0.0376(2) Uani d . 1 . O O12 0.45636(17) 0.08041(6) 0.22619(7) 0.0399(2) Uani d . 1 . O O1 0.17659(14) 0.18340(5) 0.23247(5) 0.02694(18) Uani d . 1 . O C1 -0.0594(2) 0.21676(7) 0.22970(7) 0.0242(2) Uani d . 1 . C H1 -0.1705 0.1768 0.2510 0.029 Uiso calc R 1 . H C2 -0.0574(2) 0.29299(7) 0.27857(7) 0.0268(3) Uani d . 1 . C H2 0.0514 0.3315 0.2539 0.032 Uiso calc R 1 . H C21 0.0271(3) 0.28007(9) 0.36107(8) 0.0346(3) Uani d . 1 . C H21 0.1632 0.2437 0.3583 0.042 Uiso calc R 1 . H C22 0.1097(4) 0.36032(10) 0.39459(9) 0.0463(4) Uani d . 1 . C H22A 0.2216 0.3849 0.3601 0.069 Uiso calc R 1 . H H22B 0.1812 0.3506 0.4442 0.069 Uiso calc R 1 . H H22C -0.0210 0.3967 0.4009 0.069 Uiso calc R 1 . H C23 -0.1473(4) 0.23931(12) 0.41251(10) 0.0521(5) Uani d . 1 . C H23A -0.0826 0.2330 0.4637 0.078 Uiso calc R 1 . H H23B -0.1858 0.1862 0.3918 0.078 Uiso calc R 1 . H H23C -0.2859 0.2725 0.4153 0.078 Uiso calc R 1 . H C3 -0.2974(3) 0.33104(8) 0.27332(8) 0.0351(3) Uani d . 1 . C H3A -0.4108 0.2937 0.2959 0.042 Uiso calc R 1 . H H3B -0.2999 0.3815 0.3033 0.042 Uiso calc R 1 . H C4 -0.3657(3) 0.34947(8) 0.19146(9) 0.0348(3) Uani d . 1 . C H4A -0.2621 0.3912 0.1706 0.042 Uiso calc R 1 . H H4B -0.5234 0.3713 0.1908 0.042 Uiso calc R 1 . H C5 -0.3549(2) 0.27460(8) 0.14097(8) 0.0301(3) Uani d . 1 . C H5 -0.4716 0.2352 0.1597 0.036 Uiso calc R 1 . H C51 -0.4116(3) 0.29520(10) 0.05825(9) 0.0414(4) Uani d . 1 . C H51A -0.5639 0.3198 0.0557 0.062 Uiso calc R 1 . H H51B -0.4096 0.2459 0.0276 0.062 Uiso calc R 1 . H H51C -0.2975 0.3331 0.0385 0.062 Uiso calc R 1 . H C6 -0.1185(2) 0.23517(8) 0.14734(7) 0.0283(3) Uani d . 1 . C H6A -0.1168 0.1846 0.1174 0.034 Uiso calc R 1 . H H6B -0.0015 0.2718 0.1257 0.034 Uiso calc R 1 . H C11 0.1184(2) 0.05567(7) 0.31993(7) 0.0262(3) Uani d . 1 . C C12 0.2620(2) 0.06560(8) 0.38276(8) 0.0329(3) Uani d . 1 . C H12 0.4046 0.0926 0.3777 0.039 Uiso calc R 1 . H C13 0.1929(3) 0.03539(9) 0.45259(8) 0.0369(3) Uani d . 1 . C H13 0.2904 0.0417 0.4955 0.044 Uiso calc R 1 . H C14 -0.0162(3) -0.00405(8) 0.46164(9) 0.0343(3) Uani d . 1 . C C141 -0.0858(4) -0.03860(10) 0.53729(10) 0.0487(4) Uani d . 1 . C H14A -0.0311 -0.0034 0.5783 0.073 Uiso calc R 1 . H H14B -0.0187 -0.0924 0.5432 0.073 Uiso calc R 1 . H H14C -0.2530 -0.0425 0.5397 0.073 Uiso calc R 1 . H C15 -0.1577(2) -0.01153(8) 0.39803(9) 0.0335(3) Uani d . 1 . C H15 -0.3024 -0.0371 0.4033 0.040 Uiso calc R 1 . H C16 -0.0922(2) 0.01745(8) 0.32724(8) 0.0303(3) Uani d . 1 . C H16 -0.1898 0.0113 0.2844 0.036 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 O11 S1 O12 119.81(7) O11 S1 O1 110.27(6) O12 S1 O1 103.87(6) O11 S1 C11 108.46(7) O12 S1 C11 108.84(7) O1 S1 C11 104.51(6) C1 O1 S1 119.59(7) O1 C1 C6 108.47(10) O1 C1 C2 106.43(10) C6 C1 C2 111.73(10) C1 C2 C3 107.38(11) C1 C2 C21 114.46(11) C3 C2 C21 113.82(11) C23 C21 C22 111.65(14) C23 C21 C2 113.86(13) C22 C21 C2 109.87(12) C4 C3 C2 112.17(11) C3 C4 C5 111.95(11) C4 C5 C51 111.16(11) C4 C5 C6 110.01(11) C51 C5 C6 111.10(12) C1 C6 C5 111.11(11) C16 C11 C12 120.84(13) C16 C11 S1 120.39(10) C12 C11 S1 118.74(11) C13 C12 C11 118.82(14) C12 C13 C14 121.74(13) C13 C14 C15 118.00(13) C13 C14 C141 121.11(15) C15 C14 C141 120.88(15) C16 C15 C14 121.55(13) C15 C16 C11 119.03(13) 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 O11 . 1.4300(12) ? S1 O12 . 1.4309(11) ? S1 O1 . 1.5736(10) ? S1 C11 . 1.7608(15) ? O1 C1 . 1.4866(14) ? C1 C6 . 1.5180(19) ? C1 C2 . 1.5285(18) ? C2 C3 . 1.5403(19) ? C2 C21 . 1.545(2) ? C21 C23 . 1.520(2) ? C21 C22 . 1.534(2) ? C3 C4 . 1.523(2) ? C4 C5 . 1.528(2) ? C5 C51 . 1.529(2) ? C5 C6 . 1.5323(19) ? C11 C16 . 1.3904(19) ? C11 C12 . 1.3958(19) ? C12 C13 . 1.385(2) ? C13 C14 . 1.395(2) ? C14 C15 . 1.395(2) ? C14 C141 . 1.503(2) ? C15 C16 . 1.387(2) ? 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 O11 S1 O1 C1 44.87(11) O12 S1 O1 C1 174.45(10) C11 S1 O1 C1 -71.51(10) S1 O1 C1 C6 -93.47(10) S1 O1 C1 C2 146.17(8) O1 C1 C2 C3 177.21(10) C6 C1 C2 C3 58.97(13) O1 C1 C2 C21 -55.40(13) C6 C1 C2 C21 -173.64(11) C1 C2 C21 C23 -75.60(16) C3 C2 C21 C23 48.41(16) C1 C2 C21 C22 158.32(13) C3 C2 C21 C22 -77.66(16) C1 C2 C3 C4 -57.22(14) C21 C2 C3 C4 175.03(12) C2 C3 C4 C5 56.24(17) C3 C4 C5 C51 -176.96(13) C3 C4 C5 C6 -53.47(16) O1 C1 C6 C5 -176.58(9) C2 C1 C6 C5 -59.57(13) C4 C5 C6 C1 54.95(14) C51 C5 C6 C1 178.47(11) O11 S1 C11 C16 -13.57(12) O12 S1 C11 C16 -145.46(11) O1 S1 C11 C16 104.06(10) O11 S1 C11 C12 164.32(11) O12 S1 C11 C12 32.44(12) O1 S1 C11 C12 -78.05(11) C16 C11 C12 C13 1.1(2) S1 C11 C12 C13 -176.74(11) C11 C12 C13 C14 -0.4(2) C12 C13 C14 C15 -0.9(2) C12 C13 C14 C141 178.23(14) C13 C14 C15 C16 1.5(2) C141 C14 C15 C16 -177.63(13) C14 C15 C16 C11 -0.8(2) C12 C11 C16 C15 -0.56(19) S1 C11 C16 C15 177.28(10) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 4494793