#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/91/2009113.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_2009113 loop_ _publ_author_name 'Burrows, Andrew D.' 'Harrington, Ross W.' 'Mahon, Mary F.' _publ_section_title ; 2,2'-Bipyridine-5-sulfonic acid ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1921 _journal_page_last 1923 _journal_paper_doi 10.1107/S0108270199010203 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C10 H8 N2 O3 S' _chemical_formula_sum 'C10 H8 N2 O3 S' _chemical_formula_weight 236.24 _chemical_name_systematic ; 2,2'-bipyridine-5-sulfonic 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' _audit_creation_method SHELXL _cell_angle_alpha 97.21(2) _cell_angle_beta 99.23(2) _cell_angle_gamma 96.39(2) _cell_formula_units_Z 2 _cell_length_a 6.1080(10) _cell_length_b 7.026(2) _cell_length_c 11.492(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 17.7 _cell_measurement_theta_min 15.0 _cell_volume 478.57(18) _computing_cell_refinement 'CELDIM in CAD-4-PC Software' _computing_data_collection 'CAD-4-PC Software (Enraf-Nonius, 1992)' _computing_data_reduction 'XCAD (McArdle & Higgins, 1995)' _computing_molecular_graphics 'ORTEX (McArdle, 1995)' _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.006 _diffrn_reflns_av_sigmaI/netI 0.0135 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 1913 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_min 2.95 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 80 _diffrn_standards_interval_time 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.330 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.639 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 244 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.27 _refine_diff_density_max 0.413 _refine_diff_density_min -0.324 _refine_ls_extinction_coef 0.040(7) _refine_ls_extinction_method SHELXL93 _refine_ls_goodness_of_fit_all 1.075 _refine_ls_goodness_of_fit_obs 1.105 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 147 _refine_ls_number_reflns 1681 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.126 _refine_ls_restrained_S_obs 1.105 _refine_ls_R_factor_all 0.032 _refine_ls_R_factor_obs .029 _refine_ls_shift/esd_max <0.001 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0354P)^2^+0.2614P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.082 _refine_ls_wR_factor_obs .077 _reflns_number_observed 1540 _reflns_number_total 1685 _reflns_observed_criterion I>2\s(I) _cod_data_source_file da1080.cif _cod_data_source_block ross2 _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 The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0354P)^2^+0.2614P] 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^)+(0.0354P)^2^+0.2614P] where P = (Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 478.6(2) _cod_database_code 2009113 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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 .0305(3) .0403(3) .0222(2) .0091(2) .0017(2) .0060(2) O1 .0293(7) .0864(11) .0356(7) .0061(7) -.0022(5) .0179(7) O2 .0435(7) .0454(7) .0360(7) .0123(6) .0103(6) .0162(6) O3 .0753(10) .0463(8) .0320(7) .0181(7) .0058(7) -.0029(6) N1 .0295(8) .0599(10) .0269(7) .0141(7) .0050(6) .0092(7) N2 .0315(7) .0382(8) .0259(7) .0091(6) .0023(6) .0079(6) C1 .0255(9) .0639(12) .0279(9) .0136(8) .0031(7) .0097(8) C2 .0279(8) .0309(8) .0241(8) .0064(6) .0029(6) .0050(6) C3 .0282(9) .0734(14) .0289(9) .0124(9) .0082(7) .0117(9) C4 .0238(9) .0752(14) .0330(9) .0113(9) .0024(7) .0131(9) C5 .0290(8) .0313(8) .0265(8) .0071(6) .0027(6) .0059(6) C6 .0310(8) .0277(8) .0271(8) .0039(6) .0025(7) .0060(6) C7 .0347(9) .0361(9) .0341(9) .0090(7) .0018(7) .0071(7) C8 .0385(10) .0366(9) .0380(10) .0061(8) -.0066(8) .0126(8) C9 .0482(11) .0388(10) .0260(8) .0013(8) -.0030(8) .0101(7) C10 .0437(10) .0422(10) .0253(8) .0057(8) .0057(7) .0062(7) 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 -.01387(7) .23960(6) .26140(3) .0309(2) Uani d . 1 . S O1 .2232(2) .2419(2) .26176(12) .0507(4) Uani d . 1 . O O2 -.1170(2) .0594(2) .29147(11) .0399(3) Uani d . 1 . O O3 -.0742(3) .4074(2) .32776(12) .0516(4) Uani d . 1 . O N1 -.0660(2) .2438(2) -.09032(13) .0379(4) Uani d . 1 . N N2 -.2132(2) .1880(2) -.32503(12) .0316(3) Uani d . 1 . N H2 -.0940(2) .1467(2) -.29273(12) .047(6) Uiso calc R 1 . H C1 .0047(3) .2413(3) .0253(2) .0384(4) Uani d . 1 . C H1 .1565(3) .2382(3) .0507(2) .046 Uiso calc R 1 . H C2 -.1317(3) .2429(2) .10962(14) .0276(4) Uani d . 1 . C C3 -.3569(3) .2473(3) .0725(2) .0424(5) Uani d . 1 . C H3 -.4546(3) .2489(3) .1267(2) .051 Uiso calc R 1 . H C4 -.4344(3) .2492(3) -.0472(2) .0435(5) Uani d . 1 . C H4 -.5856(3) .2518(3) -.0747(2) .052 Uiso calc R 1 . H C5 -.2845(3) .2474(2) -.12521(14) .0288(4) Uani d . 1 . C C6 -.3546(3) .2493(2) -.25438(14) .0287(4) Uani d . 1 . C C7 -.5479(3) .3117(3) -.3064(2) .0349(4) Uani d . 1 . C H7 -.6495(3) .3538(3) -.2600(2) .042 Uiso calc R 1 . H C8 -.5893(3) .3112(3) -.4288(2) .0385(4) Uani d . 1 . C H8 -.7198(3) .3524(3) -.4646(2) .046 Uiso calc R 1 . H C9 -.4387(3) .2501(3) -.4974(2) .0386(4) Uani d . 1 . C H9 -.4652(3) .2508(3) -.5793(2) .046 Uiso calc R 1 . H C10 -.2485(3) .1882(3) -.4428(2) .0370(4) Uani d . 1 . C H10 -.1444(3) .1464(3) -.4877(2) .044 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 (1992) Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables (1992) Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables (1992) Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables (1992) Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables (1992) Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 -4 6 0 -2 -8 0 2 8 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 115.02(10) y O3 S1 O2 112.42(9) y O1 S1 O2 112.51(9) y O3 S1 C2 105.89(8) y O1 S1 C2 104.44(8) y O2 S1 C2 105.51(8) y C1 N1 C5 116.97(15) y C10 N2 C6 123.35(15) y N1 C1 C2 124.4(2) y C1 C2 C3 118.0(2) ? C1 C2 S1 119.58(13) y C3 C2 S1 122.39(13) y C2 C3 C4 118.6(2) ? C5 C4 C3 119.2(2) ? N1 C5 C4 122.8(2) y N1 C5 C6 114.87(15) y C4 C5 C6 122.3(2) ? N2 C6 C7 118.34(15) y N2 C6 C5 116.19(14) y C7 C6 C5 125.5(2) ? C6 C7 C8 119.3(2) ? C9 C8 C7 120.4(2) ? C10 C9 C8 118.8(2) y N2 C10 C9 119.8(2) y N2 H2 N1 104.95(6) ? N2 H2 O2 149.40(6) ? N1 H2 N2 104.95(6) ? N1 H2 O2 100.51(8) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 O3 . . 1.4383(15) y S1 O1 . . 1.4460(14) y S1 O2 . . 1.4564(14) y S1 C2 . . 1.781(2) y N1 C1 . . 1.333(2) y N1 C5 . . 1.335(2) y N2 C10 . . 1.337(2) y N2 C6 . . 1.345(2) y C1 C2 . . 1.375(2) ? C2 C3 . . 1.378(2) ? C3 C4 . . 1.383(3) ? C4 C5 . . 1.381(2) ? C5 C6 . . 1.480(2) ? C6 C7 . . 1.377(2) ? C7 C8 . . 1.388(3) ? C8 C9 . . 1.373(3) ? C9 C10 . . 1.371(3) ? H2 O2 . . 2.043(2) ? H2 N1 . . 2.312(2) ? N1 N2 . . 2.667(2) ? C4 C7 . . 3.047(3) ? H2 O1 . . 2.043(2) ? N2 O2 . . 2.817(2) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N2 H2 O2 2_555 0.86 2.04 2.817(2) 149 yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 536035 2 PubChem 5260160