#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/60/2206019.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_2206019 loop_ _publ_author_name 'Wardell, James L.' 'Low, John N.' 'Glidewell, Christopher' _publ_section_title ; Saccharin, redetermined at 120K: a three-dimensional hydrogen-bonded framework ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1944 _journal_page_last o1946 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C7 H5 N O3 S' _chemical_formula_moiety 'C7 H5 N O3 S' _chemical_formula_sum 'C7 H5 N O3 S' _chemical_formula_weight 183.18 _chemical_name_common saccharin _chemical_name_systematic ; Saccharin ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 103.203(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.4722(4) _cell_length_b 6.9227(2) _cell_length_c 11.7322(3) _cell_measurement_reflns_used 1706 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.54 _cell_measurement_theta_min 3.57 _cell_volume 748.98(4) _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) and COLLECT' _computing_data_collection 'COLLECT (Hooft, 1999)' _computing_data_reduction 'DENZO and COLLECT' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'WinGX (Farrugia, 1999) and SIR92 (Altomare et al., 1993)' _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean 9.091 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Bruker--Nonius FR91 rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 12303 _diffrn_reflns_theta_full 27.54 _diffrn_reflns_theta_max 27.54 _diffrn_reflns_theta_min 3.57 _diffrn_standards_decay_% nil _exptl_absorpt_coefficient_mu 0.391 _exptl_absorpt_correction_T_max 0.958 _exptl_absorpt_correction_T_min 0.847 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2003)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.624 _exptl_crystal_density_method 'not measured' _exptl_crystal_description lath _exptl_crystal_F_000 376 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.417 _refine_diff_density_min -0.627 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 109 _refine_ls_number_reflns 1706 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.107 _refine_ls_R_factor_all 0.0461 _refine_ls_R_factor_gt 0.0387 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0203P)^2^+0.8656P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0890 _refine_ls_wR_factor_ref 0.0920 _reflns_number_gt 1490 _reflns_number_total 1706 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file lh6438.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2206019 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y+1/2, z+1/2' 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' N N 0.0061 0.0033 '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_ _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_type_symbol S1 0.21067(5) 0.22909(7) 0.34594(4) 0.01955(15) Uani d . 1 S O1 0.24538(17) 0.1705(2) 0.23876(12) 0.0271(3) Uani d . 1 O O2 0.08217(15) 0.3423(2) 0.33788(13) 0.0287(4) Uani d . 1 O O3 0.52054(15) 0.3079(2) 0.60463(11) 0.0216(3) Uani d . 1 O N1 0.35108(18) 0.3420(2) 0.43105(14) 0.0207(4) Uani d . 1 N C1 0.2223(2) 0.0356(3) 0.44441(16) 0.0184(4) Uani d . 1 C C2 0.1361(2) -0.1284(3) 0.43285(18) 0.0256(4) Uani d . 1 C C3 0.1685(2) -0.2627(3) 0.52349(19) 0.0271(5) Uani d . 1 C C4 0.2818(2) -0.2340(3) 0.62062(18) 0.0256(4) Uani d . 1 C C5 0.3685(2) -0.0699(3) 0.62963(17) 0.0218(4) Uani d . 1 C C6 0.3373(2) 0.0646(3) 0.54037(15) 0.0170(4) Uani d . 1 C C7 0.4147(2) 0.2483(3) 0.53308(16) 0.0177(4) Uani d . 1 C H1 0.3838 0.4622 0.4087 0.025 Uiso d R 1 H H2 0.0588 -0.1481 0.3664 0.031 Uiso calc R 1 H H3 0.1117 -0.3767 0.5188 0.033 Uiso calc R 1 H H4 0.3004 -0.3275 0.6815 0.031 Uiso calc R 1 H H5 0.4470 -0.0508 0.6953 0.026 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 0.0205(3) 0.0188(3) 0.0173(2) -0.00189(18) 0.00002(17) -0.00062(17) O1 0.0372(9) 0.0252(8) 0.0189(7) -0.0036(6) 0.0067(6) -0.0018(6) O2 0.0221(8) 0.0307(8) 0.0303(8) 0.0049(6) -0.0002(6) 0.0014(6) O3 0.0239(7) 0.0222(7) 0.0169(6) -0.0054(6) 0.0008(5) -0.0016(5) N1 0.0235(9) 0.0165(8) 0.0195(8) -0.0048(6) -0.0003(6) 0.0015(6) C1 0.0204(9) 0.0176(9) 0.0176(9) -0.0012(7) 0.0053(7) -0.0021(7) C2 0.0225(10) 0.0275(11) 0.0264(10) -0.0062(9) 0.0048(8) -0.0070(9) C3 0.0307(11) 0.0191(10) 0.0349(11) -0.0085(8) 0.0146(9) -0.0033(8) C4 0.0344(12) 0.0202(10) 0.0253(10) -0.0029(8) 0.0130(9) 0.0015(8) C5 0.0279(10) 0.0196(9) 0.0186(9) -0.0012(8) 0.0067(8) 0.0001(7) C6 0.0197(9) 0.0161(9) 0.0159(8) -0.0010(7) 0.0056(7) -0.0034(7) C7 0.0197(9) 0.0168(9) 0.0174(9) -0.0017(7) 0.0057(7) -0.0027(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 O1 1.4291(15) y S1 O2 1.4323(15) y S1 N1 1.6643(16) y S1 C1 1.7560(19) y N1 C7 1.374(2) y N1 H1 0.9462 no C7 O3 1.223(2) y C7 C6 1.481(3) y C1 C2 1.387(3) y C2 C3 1.393(3) y C2 H2 0.95 no C3 C4 1.390(3) y C3 H3 0.95 no C4 C5 1.392(3) y C4 H4 0.95 no C5 C6 1.382(3) y C5 H5 0.95 no C6 C1 1.391(3) y 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 O1 S1 O2 117.37(9) y O1 S1 N1 110.37(9) y O2 S1 N1 109.48(9) y O1 S1 C1 111.71(9) y O2 S1 C1 112.68(9) y N1 S1 C1 92.41(8) y S1 N1 C7 115.65(13) y C7 N1 H1 123.4 no S1 N1 H1 120.9 no O3 C7 N1 124.53(17) y O3 C7 C6 126.12(17) y N1 C7 C6 109.34(16) y C2 C1 C6 122.17(18) no C2 C1 S1 127.80(15) no S1 C1 C6 110.01(14) y C1 C2 C3 116.72(18) no C1 C2 H2 121.6 no C3 C2 H2 121.6 no C4 C3 C2 121.65(19) no C4 C3 H3 119.2 no C2 C3 H3 119.2 no C3 C4 C5 120.71(19) no C3 C4 H4 119.6 no C5 C4 H4 119.6 no C6 C5 C4 118.18(18) no C6 C5 H5 120.9 no C4 C5 H5 120.9 no C5 C6 C1 120.57(18) no C5 C6 C7 126.84(17) no C1 C6 C7 112.59(16) ny 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 O1 S1 N1 C7 -113.64(15) no O2 S1 N1 C7 115.70(15) no C1 S1 N1 C7 0.60(16) no S1 N1 C7 O3 178.42(15) no S1 N1 C7 C6 -0.3(2) no O1 S1 C1 C2 -66.2(2) no O2 S1 C1 C2 68.4(2) no N1 S1 C1 C2 -179.26(19) no O1 S1 C1 C6 112.34(14) no O2 S1 C1 C6 -113.01(14) no N1 S1 C1 C6 -0.72(15) no C6 C1 C2 C3 1.1(3) no S1 C1 C2 C3 179.43(16) no C1 C2 C3 C4 -0.1(3) no C2 C3 C4 C5 -0.9(3) no C3 C4 C5 C6 1.0(3) no C4 C5 C6 C1 -0.1(3) no C4 C5 C6 C7 179.60(18) no C2 C1 C6 C5 -1.0(3) no S1 C1 C6 C5 -179.60(15) no C2 C1 C6 C7 179.32(18) no S1 C1 C6 C7 0.7(2) no O3 C7 C6 C5 1.3(3) no N1 C7 C6 C5 -179.96(18) no O3 C7 C6 C1 -178.97(19) no N1 C7 C6 C1 -0.3(2) no 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 N1 H1 O3 3_666 0.95 1.86 2.786(2) 167 y C2 H2 O2 2_545 0.95 2.46 3.377(3) 161 y C4 H4 O1 4_545 0.95 2.55 3.375(2) 145 y C5 H5 O3 2_646 0.95 2.50 3.169(2) 128 y _cod_database_fobs_code 2206019