#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/27/2012712.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_2012712 loop_ _publ_author_name 'Sethu Sankar, K.' 'Velmurugan, D.' 'Thirumamagal, B. T. S.' 'Shanmuga Sundara Raj, S.' 'Fun, H.-K.' 'Moon, Jib-Kim' _publ_section_title ; 2-[1-(Phenylsulfonyl)ethyl]benzoic acid and 2-[1-(phenylsulfonyl)propyl]benzoic acid ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o257 _journal_page_last o259 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C16 H16 O4 S' _chemical_formula_sum 'C16 H16 O4 S' _chemical_formula_weight 304.35 _chemical_name_systematic ; 2-[1-(Phenylsulfonyl)propyl]benzoic acid ; _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 SHELXL97 _cell_angle_alpha 94.634(9) _cell_angle_beta 91.8070(10) _cell_angle_gamma 116.020(8) _cell_formula_units_Z 2 _cell_length_a 7.4805(10) _cell_length_b 7.5125(9) _cell_length_c 14.4853(18) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.97 _cell_measurement_theta_min 2.83 _cell_volume 727.09(17) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'SDP (Frenz, 1989)' _computing_molecular_graphics 'ZORTEP (Zsolnai, 1997)' _computing_publication_material 'SHELX97 and PARST (Nardelli, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _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 0.016 _diffrn_reflns_av_sigmaI/netI 0.030 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2625 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_min 2.83 _diffrn_standards_decay_% 1 _diffrn_standards_interval_time 300 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.235 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 320 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.26 _refine_diff_density_max 0.28 _refine_diff_density_min -0.19 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 192 _refine_ls_number_reflns 2518 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.014 _refine_ls_R_factor_all 0.056 _refine_ls_R_factor_gt 0.040 _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^)+(0.0549P)^2^+0.1743P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.098 _refine_ls_wR_factor_ref 0.107 _reflns_number_gt 2004 _reflns_number_total 2518 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file na1557.cif _[local]_cod_data_source_block II _[local]_cod_cif_authors_sg_H-M P-1 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 'Triclinic' changed to 'triclinic' 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 ; _cod_original_cell_volume 727.09(16) _cod_database_code 2012712 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 S1 0.20708(8) 0.44293(8) 0.16910(4) 0.04162(19) Uani d . 1 . . S O1 0.3803(2) 0.5780(2) 0.42924(12) 0.0561(5) Uani d . 1 . . O O2 0.2830(3) 0.3211(2) 0.21172(12) 0.0603(5) Uani d . 1 . . O O3 0.2600(3) 0.2837(3) 0.48350(13) 0.0654(5) Uani d . 1 . . O H3 0.3736 0.3305 0.5082 0.098 Uiso calc R 1 . . H O4 0.0334(2) 0.3469(2) 0.10488(11) 0.0559(5) Uani d . 1 . . O C1 0.0374(3) 0.3470(3) 0.38971(14) 0.0374(5) Uani d . 1 . . C C2 -0.0049(3) 0.4326(3) 0.31428(14) 0.0371(5) Uani d . 1 . . C C3 -0.2037(3) 0.3623(3) 0.28149(17) 0.0494(6) Uani d . 1 . . C H3A -0.2340 0.4178 0.2318 0.059 Uiso calc R 1 . . H C4 -0.3568(3) 0.2135(4) 0.32024(18) 0.0561(6) Uani d . 1 . . C H4 -0.4882 0.1711 0.2973 0.067 Uiso calc R 1 . . H C5 -0.3145(4) 0.1279(4) 0.39295(18) 0.0564(6) Uani d . 1 . . C H5 -0.4172 0.0263 0.4190 0.068 Uiso calc R 1 . . H C6 -0.1199(3) 0.1931(3) 0.42713(16) 0.0489(6) Uani d . 1 . . C H6 -0.0922 0.1338 0.4760 0.059 Uiso calc R 1 . . H C7 0.2418(3) 0.4146(3) 0.43423(14) 0.0411(5) Uani d . 1 . . C C8 0.1556(3) 0.5853(3) 0.26256(14) 0.0377(5) Uani d . 1 . . C H8 0.2763 0.6521 0.3049 0.045 Uiso calc R 1 . . H C9 0.1063(3) 0.7462(3) 0.22693(15) 0.0441(5) Uani d . 1 . . C H9A 0.2163 0.8339 0.1939 0.053 Uiso calc R 1 . . H H9B -0.0112 0.6839 0.1837 0.053 Uiso calc R 1 . . H C10 0.0687(4) 0.8674(4) 0.30598(17) 0.0550(6) Uani d . 1 . . C H10A -0.0538 0.7858 0.3319 0.082 Uiso calc R 1 . . H H10B 0.0592 0.9796 0.2830 0.082 Uiso calc R 1 . . H H10C 0.1768 0.9136 0.3531 0.082 Uiso calc R 1 . . H C11 0.3998(3) 0.6215(3) 0.11182(15) 0.0383(5) Uani d . 1 . . C C12 0.5860(3) 0.7331(3) 0.15787(17) 0.0486(6) Uani d . 1 . . C H12 0.6107 0.7158 0.2190 0.058 Uiso calc R 1 . . H C13 0.7347(3) 0.8709(4) 0.11141(19) 0.0550(6) Uani d . 1 . . C H13 0.8600 0.9485 0.1418 0.066 Uiso calc R 1 . . H C14 0.6984(4) 0.8939(4) 0.02084(19) 0.0551(6) Uani d . 1 . . C H14 0.7999 0.9852 -0.0103 0.066 Uiso calc R 1 . . H C15 0.5130(4) 0.7828(4) -0.02414(17) 0.0514(6) Uani d . 1 . . C H15 0.4896 0.7990 -0.0856 0.062 Uiso calc R 1 . . H C16 0.3613(3) 0.6473(3) 0.02139(15) 0.0446(5) Uani d . 1 . . C H16 0.2347 0.5743 -0.0085 0.053 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 S1 0.0417(3) 0.0341(3) 0.0467(3) 0.0141(2) 0.0052(2) 0.0067(2) O1 0.0477(10) 0.0464(10) 0.0633(11) 0.0102(8) -0.0162(8) 0.0170(8) O2 0.0758(12) 0.0514(10) 0.0719(12) 0.0401(9) 0.0239(9) 0.0268(9) O3 0.0529(11) 0.0533(10) 0.0794(13) 0.0122(8) -0.0198(9) 0.0273(9) O4 0.0447(9) 0.0477(9) 0.0539(10) 0.0031(8) -0.0003(8) -0.0063(8) C1 0.0414(12) 0.0378(11) 0.0338(11) 0.0182(10) 0.0030(9) 0.0032(9) C2 0.0355(11) 0.0367(11) 0.0369(11) 0.0141(9) 0.0012(9) 0.0033(9) C3 0.0391(13) 0.0542(14) 0.0528(14) 0.0185(11) -0.0034(10) 0.0104(11) C4 0.0338(12) 0.0625(16) 0.0657(16) 0.0155(12) 0.0012(11) 0.0090(13) C5 0.0422(14) 0.0572(15) 0.0598(16) 0.0113(12) 0.0144(12) 0.0125(12) C6 0.0502(14) 0.0509(14) 0.0430(13) 0.0185(11) 0.0072(11) 0.0123(11) C7 0.0472(13) 0.0403(12) 0.0363(12) 0.0199(11) -0.0003(10) 0.0062(9) C8 0.0365(11) 0.0363(11) 0.0364(11) 0.0130(9) -0.0036(9) 0.0047(9) C9 0.0504(13) 0.0395(12) 0.0443(13) 0.0215(11) 0.0004(10) 0.0069(10) C10 0.0661(16) 0.0462(14) 0.0548(15) 0.0269(12) 0.0072(12) 0.0039(11) C11 0.0375(11) 0.0343(11) 0.0445(12) 0.0167(9) 0.0047(9) 0.0059(9) C12 0.0424(13) 0.0462(13) 0.0541(14) 0.0165(11) -0.0030(11) 0.0095(11) C13 0.0366(13) 0.0460(14) 0.0766(18) 0.0130(11) -0.0002(12) 0.0085(12) C14 0.0526(15) 0.0443(13) 0.0725(18) 0.0222(12) 0.0217(13) 0.0181(12) C15 0.0637(16) 0.0523(14) 0.0438(13) 0.0293(13) 0.0104(12) 0.0111(11) C16 0.0469(13) 0.0411(12) 0.0457(13) 0.0196(10) 0.0022(10) 0.0046(10) 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 O2 . 1.437(2) y S1 O4 . 1.438(2) y S1 C11 . 1.767(2) y S1 C8 . 1.813(2) ? O1 C7 . 1.220(3) y O3 C7 . 1.311(2) y O3 H3 . 0.8200 ? C1 C6 . 1.401(3) ? C1 C2 . 1.407(3) ? C1 C7 . 1.488(3) ? C2 C3 . 1.393(3) ? C2 C8 . 1.518(3) ? C3 C4 . 1.377(3) ? C3 H3A . 0.9300 ? C4 C5 . 1.374(3) ? C4 H4 . 0.9300 ? C5 C6 . 1.377(3) ? C5 H5 . 0.9300 ? C6 H6 . 0.9300 ? C8 C9 . 1.531(3) ? C8 H8 . 0.9800 ? C9 C10 . 1.515(3) ? C9 H9A . 0.9700 ? C9 H9B . 0.9700 ? C10 H10A . 0.9600 ? C10 H10B . 0.9600 ? C10 H10C . 0.9600 ? C11 C12 . 1.384(3) ? C11 C16 . 1.379(3) ? C12 C13 . 1.382(3) ? C12 H12 . 0.9300 ? C13 C14 . 1.371(4) ? C13 H13 . 0.9300 ? C14 C15 . 1.372(3) ? C14 H14 . 0.9300 ? C15 C16 . 1.379(3) ? C15 H15 . 0.9300 ? C16 H16 . 0.9300 ? 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 O2 S1 O4 118.47(11) ? O2 S1 C11 108.79(10) ? O4 S1 C11 108.10(10) y O2 S1 C8 106.80(10) y O4 S1 C8 108.80(10) y C11 S1 C8 105.20(10) ? C7 O3 H3 109.5 ? C6 C1 C2 119.08(19) ? C6 C1 C7 117.51(19) ? C2 C1 C7 123.39(18) ? C3 C2 C1 117.93(19) ? C3 C2 C8 118.64(19) ? C1 C2 C8 123.25(18) ? C4 C3 C2 122.2(2) ? C4 C3 H3A 118.9 ? C2 C3 H3A 118.9 ? C3 C4 C5 119.7(2) ? C3 C4 H4 120.2 ? C5 C4 H4 120.2 ? C4 C5 C6 119.8(2) ? C4 C5 H5 120.1 ? C6 C5 H5 120.1 ? C5 C6 C1 121.3(2) ? C5 C6 H6 119.4 ? C1 C6 H6 119.4 ? O1 C7 O3 121.8(2) y O1 C7 C1 124.5(2) y O3 C7 C1 113.7(2) y C2 C8 C9 115.77(17) ? C2 C8 S1 105.60(10) y C9 C8 S1 111.90(10) y C2 C8 H8 107.7 ? C9 C8 H8 107.7 ? S1 C8 H8 107.7 ? C10 C9 C8 111.36(18) ? C10 C9 H9A 109.4 ? C8 C9 H9A 109.4 ? C10 C9 H9B 109.4 ? C8 C9 H9B 109.4 ? H9A C9 H9B 108.0 ? C9 C10 H10A 109.5 ? C9 C10 H10B 109.5 ? H10A C10 H10B 109.5 ? C9 C10 H10C 109.5 ? H10A C10 H10C 109.5 ? H10B C10 H10C 109.5 ? C12 C11 C16 121.0(2) ? C12 C11 S1 119.92(17) ? C16 C11 S1 119.10(17) ? C11 C12 C13 118.8(2) ? C11 C12 H12 120.6 ? C13 C12 H12 120.6 ? C14 C13 C12 120.4(2) ? C14 C13 H13 119.8 ? C12 C13 H13 119.8 ? C13 C14 C15 120.3(2) ? C13 C14 H14 119.8 ? C15 C14 H14 119.8 ? C16 C15 C14 120.3(2) ? C16 C15 H15 119.8 ? C14 C15 H15 119.8 ? C15 C16 C11 119.1(2) ? C15 C16 H16 120.4 ? C11 C16 H16 120.4 ? 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 _geom_hbond_publ_flag C6 H6 O3 1_555 0.93 2.36 2.695(3) 101 y C8 H8 O1 1_555 0.98 2.15 2.917(3) 134 y C16 H16 O4 1_555 0.93 2.50 2.887(3) 105 y O3 H3 O1 2_666 0.82 1.83 2.652(3) 175 y 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 _geom_torsion_publ_flag C6 C1 C2 C3 1.4(3) ? C7 C1 C2 C3 -177.04(19) ? C6 C1 C2 C8 -173.70(19) ? C7 C1 C2 C8 7.9(3) ? C1 C2 C3 C4 -0.2(3) ? C8 C2 C3 C4 175.1(2) ? C2 C3 C4 C5 -0.9(4) ? C3 C4 C5 C6 0.7(4) ? C4 C5 C6 C1 0.5(4) ? C2 C1 C6 C5 -1.6(3) ? C7 C1 C6 C5 176.9(2) ? C6 C1 C7 O1 -157.2(2) ? C2 C1 C7 O1 21.2(3) ? C6 C1 C7 O3 20.3(3) ? C2 C1 C7 O3 -161.2(2) ? C3 C2 C8 C9 39.7(3) ? C1 C2 C8 C9 -145.3(2) ? C3 C2 C8 S1 -84.7(2) ? C1 C2 C8 S1 90.3(2) ? O2 S1 C8 C2 -62.6(2) y O4 S1 C8 C2 66.3(2) y C11 S1 C8 C2 -178.10(10) y O2 S1 C8 C9 170.6(2) y O4 S1 C8 C9 -60.5(2) y C11 S1 C8 C9 55.1(2) y C2 C8 C9 C10 60.3(2) ? S1 C8 C9 C10 -178.58(16) ? O2 S1 C11 C12 -48.9(2) y O4 S1 C11 C12 -178.7(2) y C8 S1 C11 C12 65.2(2) y O2 S1 C11 C16 131.2(2) y O4 S1 C11 C16 1.4(2) y C8 S1 C11 C16 -114.7(2) y C16 C11 C12 C13 -0.5(3) ? S1 C11 C12 C13 179.6(2) y C11 C12 C13 C14 -1.0(4) ? C12 C13 C14 C15 1.2(4) ? C13 C14 C15 C16 0.2(4) ? C14 C15 C16 C11 -1.6(3) ? C12 C11 C16 C15 1.8(3) ? S1 C11 C16 C15 -178.3(2) y _cod_database_fobs_code 2012712 _journal_paper_doi 10.1107/S0108270102004389