#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/04/2200404.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_2200404 loop_ _publ_author_name 'Bond, Andrew D.' 'Feeder, Neil' 'Redman, James E.' 'Sanders, Jeremy K. M.' _publ_section_title ; 4,4'-Bipyridine-3,3'-dicarboxylic acid dihydrate ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o869 _journal_page_last o871 _journal_paper_doi 10.1107/S1600536801013939 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C12 H8 N2 O4, 2H2 O' _chemical_formula_moiety 'C12 H8 N2 O4, 2H2 O' _chemical_formula_sum 'C12 H12 N2 O6' _chemical_formula_weight 280.24 _chemical_name_systematic ; 4,4'-Bipyridine-2,2'-dicarboxylic acid dihydrate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _cell_angle_alpha 90.00 _cell_angle_beta 110.770(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.5200(10) _cell_length_b 15.970(2) _cell_length_c 9.6700(10) _cell_measurement_reflns_used 3856 _cell_measurement_temperature 130(2) _cell_measurement_theta_max 25.20 _cell_measurement_theta_min 2.55 _cell_volume 1230.2(3) _computing_cell_refinement 'R-AXIS PROCESS' _computing_data_collection 'R-AXIS PROCESS (Molecular Structure Corporation, 1997)' _computing_data_reduction 'R-AXIS PROCESS' _computing_molecular_graphics 'XP (Sheldrick, 1993)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 130(2) _diffrn_measured_fraction_theta_full .957 _diffrn_measured_fraction_theta_max .957 _diffrn_measurement_device_type 'Rigaku R-AXIS IIc' _diffrn_measurement_method 'thin-slice \f' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0427 _diffrn_reflns_av_sigmaI/netI .1353 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 3856 _diffrn_reflns_theta_full 25.20 _diffrn_reflns_theta_max 25.20 _diffrn_reflns_theta_min 2.55 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .123 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 584 _exptl_crystal_size_max .15 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .10 _refine_diff_density_max .222 _refine_diff_density_min -.303 _refine_ls_extinction_coef .037(2) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref .941 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 200 _refine_ls_number_reflns 2126 _refine_ls_number_restraints 8 _refine_ls_restrained_S_all .940 _refine_ls_R_factor_all .1032 _refine_ls_R_factor_gt .0548 _refine_ls_shift/su_max .003 _refine_ls_shift/su_mean .001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0246P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1082 _reflns_number_gt 1270 _reflns_number_total 2126 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bt6080.cif _cod_data_source_block I _cod_original_cell_volume 1230.2(2) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2200404 _cod_database_fobs_code 2200404 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 C1 .2699(4) -.50742(17) .1406(3) .0153(7) Uani d . 1 . . C C2 .1921(4) -.44721(17) .0318(3) .0167(7) Uani d . 1 . . C C3 .1996(4) -.45680(18) -.1068(3) .0196(7) Uani d . 1 . . C H3 .1490 -.4158 -.1804 .024 Uiso calc R 1 . . H N4 .2767(3) -.52267(15) -.1407(3) .0187(6) Uani d D 1 . . N H4 .272(4) -.5270(19) -.2328(15) .022 Uiso d D 1 . . H C5 .3494(4) -.58138(18) -.0411(3) .0194(7) Uani d . 1 . . C H5 .4024 -.6278 -.0678 .023 Uiso calc R 1 . . H C6 .3481(4) -.57530(18) .1005(3) .0193(7) Uani d . 1 . . C H6 .4006 -.6174 .1712 .023 Uiso calc R 1 . . H C7 .0920(4) -.37288(17) .0550(4) .0201(7) Uani d . 1 . . C O1 .0663(3) -.31695(12) -.0457(2) .0320(6) Uani d . 1 . . O O2 .0392(2) -.37279(12) .1584(2) .0214(5) Uani d . 1 . . O C1A .2680(4) -.50708(18) .2946(3) .0166(7) Uani d . 1 . . C C2A .3154(4) -.43927(17) .3927(3) .0166(7) Uani d . 1 . . C C3A .3040(4) -.44974(18) .5329(3) .0182(7) Uani d . 1 . . C H3A .3321 -.4035 .5988 .022 Uiso calc R 1 . . H N4A .2560(3) -.52076(14) .5794(3) .0196(6) Uani d . 1 . . N C5A .2140(4) -.58539(19) .4865(3) .0215(7) Uani d . 1 . . C H5A .1807 -.6363 .5189 .026 Uiso calc R 1 . . H C6A .2168(4) -.58110(18) .3437(4) .0195(7) Uani d . 1 . . C H6A .1842 -.6282 .2799 .023 Uiso calc R 1 . . H C7A .3865(4) -.35780(18) .3627(3) .0188(7) Uani d . 1 . . C O1A .3838(3) -.29998(12) .4557(3) .0311(6) Uani d D 1 . . O H1A .458(3) -.2641(15) .455(4) .037 Uiso d D 1 . . H O2A .4433(3) -.35072(12) .2629(2) .0220(5) Uani d . 1 . . O O3 .4464(3) -.24391(14) -.1605(3) .0322(6) Uani d D 1 . . O H31 .481(3) -.2110(16) -.212(3) .039 Uiso d D 1 . . H H32 .350(2) -.2609(19) -.213(3) .039 Uiso d D 1 . . H O4 .1072(3) -.28403(14) -.3433(3) .0286(6) Uani d D 1 . . O H41 .079(4) -.277(2) -.4352(13) .034 Uiso d D 1 . . H H42 .042(3) -.2574(17) -.311(3) .034 Uiso d D 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 C1 .0146(16) .0175(14) .0137(16) -.0048(13) .0049(14) -.0027(14) C2 .0174(16) .0174(14) .0142(16) -.0038(13) .0041(14) -.0009(13) C3 .0217(17) .0201(15) .0160(17) .0007(14) .0054(15) .0021(14) N4 .0241(15) .0208(13) .0118(14) .0006(12) .0074(13) .0001(12) C5 .0242(18) .0152(14) .0220(18) -.0001(14) .0121(15) -.0007(15) C6 .0243(17) .0165(15) .0177(17) .0025(14) .0080(14) .0028(14) C7 .0215(18) .0173(14) .0188(18) -.0006(14) .0038(15) .0000(15) O1 .0519(16) .0232(11) .0269(13) .0174(12) .0214(13) .0101(11) O2 .0243(12) .0243(11) .0185(12) .0030(10) .0113(11) -.0005(10) C1A .0162(16) .0189(14) .0152(17) .0029(14) .0061(15) .0013(14) C2A .0159(15) .0154(14) .0176(17) -.0015(13) .0050(14) -.0003(13) C3A .0193(16) .0204(15) .0180(17) .0007(14) .0104(14) -.0023(14) N4A .0239(15) .0200(13) .0159(14) .0022(12) .0085(12) .0028(12) C5A .0249(18) .0212(15) .0192(17) -.0006(15) .0087(15) .0033(15) C6A .0218(17) .0178(15) .0162(17) -.0014(14) .0035(15) -.0019(14) C7A .0181(17) .0184(15) .0185(18) -.0011(14) .0050(15) -.0016(14) O1A .0469(16) .0189(11) .0359(15) -.0129(12) .0250(14) -.0090(12) O2A .0260(12) .0232(11) .0199(12) -.0043(10) .0119(11) -.0017(10) O3 .0335(15) .0336(13) .0290(14) -.0066(12) .0104(12) .0044(13) O4 .0349(15) .0293(12) .0265(13) .0005(11) .0168(12) -.0013(12) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 '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 C6 C1 C2 117.9(3) no C6 C1 C1A 117.0(3) no C2 C1 C1A 125.0(3) no C3 C2 C1 118.8(3) no C3 C2 C7 116.9(3) no C1 C2 C7 124.3(3) no N4 C3 C2 121.5(3) no N4 C3 H3 119.3 no C2 C3 H3 119.3 no C5 N4 C3 121.2(3) no C5 N4 H4 121(2) no C3 N4 H4 117(2) no N4 C5 C6 120.3(3) no N4 C5 H5 119.8 no C6 C5 H5 119.8 no C5 C6 C1 120.2(3) no C5 C6 H6 119.9 no C1 C6 H6 119.9 no O2 C7 O1 127.0(3) no O2 C7 C2 120.3(3) no O1 C7 C2 112.6(3) no C6A C1A C2A 118.2(3) no C6A C1A C1 116.7(3) no C2A C1A C1 125.1(3) no C1A C2A C3A 117.4(3) no C1A C2A C7A 125.2(3) no C3A C2A C7A 117.4(3) no N4A C3A C2A 124.1(3) no N4A C3A H3A 118.0 no C2A C3A H3A 118.0 no C5A N4A C3A 118.2(3) no N4A C5A C6A 122.4(3) no N4A C5A H5A 118.8 no C6A C5A H5A 118.8 no C5A C6A C1A 119.7(3) no C5A C6A H6A 120.1 no C1A C6A H6A 120.1 no O2A C7A O1A 126.1(3) no O2A C7A C2A 121.9(3) no O1A C7A C2A 112.0(3) no C7A O1A H1A 106(2) no H31 O3 H32 108(2) no H41 O4 H42 110(2) no 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 C1 C6 . 1.397(4) no C1 C2 . 1.405(4) no C1 C1A . 1.495(4) no C2 C3 . 1.373(4) no C2 C7 . 1.524(4) no C3 N4 . 1.341(4) no C3 H3 . .9500 no N4 C5 . 1.330(4) no N4 H4 . .880(10) no C5 C6 . 1.376(4) no C5 H5 . .9500 no C6 H6 . .9500 no C7 O2 . 1.233(4) no C7 O1 . 1.282(3) no C1A C6A . 1.400(4) no C1A C2A . 1.401(4) no C2A C3A . 1.403(4) no C2A C7A . 1.506(4) no C3A N4A . 1.336(4) no C3A H3A . .9500 no N4A C5A . 1.331(4) no C5A C6A . 1.391(4) no C5A H5A . .9500 no C6A H6A . .9500 no C7A O2A . 1.228(3) no C7A O1A . 1.295(3) no O1A H1A . .850(10) no O3 H31 . .850(10) no O3 H32 . .840(10) no O4 H41 . .840(10) no O4 H42 . .840(10) 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 N4 H4 N4A 1_554 .880(10) 1.780(10) 2.650(4) 172(3) yes O1A H1A O1 4_656 .850(10) 1.590(10) 2.433(3) 168(3) yes O3 H32 O4 . .840(10) 2.040(10) 2.875(3) 172(3) yes O3 H31 O2 4_655 .850(10) 2.010(10) 2.854(3) 174(3) yes O4 H41 O3 4 .840(10) 2.090(10) 2.916(3) 165(3) yes O4 H42 O2A 4 .840(10) 2.15(2) 2.942(3) 156(3) yes C3 H3 O4 . .95 2.58 3.491(4) 161.4 yes C5A H5A O3 2_545 .95 2.66 3.569(4) 161.4 yes 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(4) no C1A C1 C2 C3 -178.0(3) no C6 C1 C2 C7 175.8(3) no C1A C1 C2 C7 -.8(4) no C1 C2 C3 N4 1.1(4) no C7 C2 C3 N4 -176.3(3) no C2 C3 N4 C5 -.1(4) no C3 N4 C5 C6 -.5(4) no N4 C5 C6 C1 .2(4) no C2 C1 C6 C5 .8(4) no C1A C1 C6 C5 177.6(3) no C3 C2 C7 O2 159.2(3) no C1 C2 C7 O2 -18.0(4) no C3 C2 C7 O1 -17.8(4) no C1 C2 C7 O1 165.0(3) no C6 C1 C1A C6A -48.4(4) no C2 C1 C1A C6A 128.2(3) no C6 C1 C1A C2A 130.7(3) no C2 C1 C1A C2A -52.7(4) no C6A C1A C2A C3A -1.6(4) no C1 C1A C2A C3A 179.3(3) no C6A C1A C2A C7A 174.9(3) no C1 C1A C2A C7A -4.2(5) no C1A C2A C3A N4A 2.2(5) no C7A C2A C3A N4A -174.6(3) no C2A C3A N4A C5A -1.0(5) no C3A N4A C5A C6A -.6(5) no N4A C5A C6A C1A 1.0(5) no C2A C1A C6A C5A .1(4) no C1 C1A C6A C5A 179.3(3) no C1A C2A C7A O2A -16.5(5) no C3A C2A C7A O2A 160.0(3) no C1A C2A C7A O1A 165.4(3) no C3A C2A C7A O1A -18.1(4) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21132735 2 PubChem 85791634