#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/02/2010267.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_2010267 loop_ _publ_author_name 'Sommerer, S.O.' 'Westcott, B.L.' 'Friebe, T.L.' 'Abboud, K.A.' _publ_section_title ; Di(2-pyridinio)methanediol dinitrate ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 2013 _journal_page_last 2015 _journal_paper_doi 10.1107/S0108270194004488 _journal_volume 50 _journal_year 1994 _chemical_formula_moiety 'C11 H12 N2 O2 2+, 2N O3 1-' _chemical_formula_sum 'C11 H12 N4 O8' _chemical_formula_weight 328.25 _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_type_scat_source IntTabIV _cell_angle_alpha 90. _cell_angle_beta 100.38(2) _cell_angle_gamma 90. _cell_formula_units_Z 4 _cell_length_a 10.292(2) _cell_length_b 11.2190(10) _cell_length_c 12.481(2) _cell_measurement_reflns_used 50 _cell_measurement_temperature 295 _cell_measurement_theta_max 11 _cell_measurement_theta_min 10 _cell_volume 1417.5(4) _diffrn_measurement_device 'Siemens R3m/V' _diffrn_measurement_method \w _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0138 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 4597 _diffrn_reflns_theta_max 30 _diffrn_standards_decay_% 1 _diffrn_standards_interval_count 100 _diffrn_standards_number 4 _exptl_absorpt_coefficient_mu 0.13 _exptl_absorpt_correction_T_max 0.971 _exptl_absorpt_correction_T_min 0.950 _exptl_absorpt_correction_type analytical _exptl_crystal_colour orange-yellow _exptl_crystal_density_diffrn 1.538 _exptl_crystal_description blocks _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.34 _refine_diff_density_max 0.27 _refine_diff_density_min -0.22 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 2.03 _refine_ls_hydrogen_treatment refall _refine_ls_number_parameters 256 _refine_ls_number_reflns 2906 _refine_ls_R_factor_obs 0.0481 _refine_ls_shift/esd_max 0.001 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0004F]^2^' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.0617 _reflns_number_observed 2906 _reflns_number_total 4174 _reflns_observed_criterion F>4\s(F) _cod_data_source_file cr1106.cif _cod_data_source_block cr1106a _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value '1/[\s^2^(F) + 0.0004F]^2^' 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^(F) + 0.0004F]^2^'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2010267 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x+1/2,y+1/2,-z+1/2 3 -x,-y,-z 4 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 N1 .22771(13) .39427(14) .32551(12) .0399(4) N1' .59761(13) .24926(13) .20434(12) .0367(4) O1a .47614(13) .44805(13) .18028(12) .0545(5) O1b .47018(12) .45487(12) .36585(11) .0520(5) C1 .4450(2) .3889(2) .26970(14) .0388(5) C2 .2983(2) .3551(2) .25287(13) .0365(5) C2' .52694(14) .27462(14) .28178(13) .0360(5) C3 .2387(2) .2845(2) .1693(2) .0480(6) C3' .5315(2) .1987(2) .3685(2) .0495(6) C4 .1076(2) .2528(2) .1630(2) .0530(6) C4' .6139(2) .1014(2) .3772(2) .0625(8) C5 .0383(2) .2940(2) .2393(2) .0539(7) C5' .6894(2) .0801(2) .2985(2) .0599(8) C6 .0998(2) .3653(2) .3206(2) .0510(6) C6' .6781(2) .1544(2) .2116(2) .0470(6) N' .2214(2) .14352(14) .47851(12) .0467(5) O1' .1120(2) .1364(2) .50440(14) .0861(7) O2' .3080(2) .2048(2) .53228(14) .0808(7) O3' .2416(2) .0888(2) .39624(12) .0655(6) N .18931(13) .58795(13) .53806(12) .0416(5) O1 .1977(2) .6294(2) .62979(13) .0701(6) O2 .09190(14) .6014(2) .46737(12) .0675(6) O3 .28523(12) .5263(2) .51775(11) .0645(5) H1 .264(2) .433(2) .381(2) .051(6) H1' .591(2) .294(2) .149(2) .046(5) H1a .417(3) .502(2) .154(2) .078(8) H1b .553(3) .457(2) .396(2) .071(7) H3 .288(2) .258(2) .124(2) .055(6) H3' .480(2) .217(2) .422(2) .063(6) H4 .065(2) .196(2) .109(2) .059(6) H4' .618(2) .048(2) .439(2) .064(6) H5 -.051(2) .273(2) .241(2) .063(6) H5' .749(2) .019(2) .306(2) .069(7) H6 .064(2) .401(2) .377(2) .066(6) H6' .719(2) .147(2) .157(2) .055(6) 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 C2 N1 C6 122.5(2) yes C2' N1' C6' 121.9(2) yes C2 C1 C2' 108.57(13) yes C2 C1 O1a 111.90(13) yes C2 C1 O1b 105.95(14) yes C2' C1 O1a 106.15(14) yes C2' C1 O1b 110.31(13) yes O1a C1 O1b 113.89(14) yes C3 C2 N1 119.0(2) yes C3 C2 C1 123.0(2) yes N1 C2 C1 117.95(14) yes C3' C2' N1' 119.4(2) yes C3' C2' C1 122.6(2) yes N1' C2' C1 117.95(15) yes C4 C3 C2 119.5(2) yes C4' C3' C2' 119.3(2) yes C5 C4 C3 119.9(2) yes C5' C4' C3' 120.0(2) yes C6 C5 C4 119.2(2) yes C6' C5' C4' 119.0(2) yes N1 C6 C5 119.9(2) yes N1' C6' C5' 120.3(2) yes O1' N' O2' 120.2(2) yes O2' N' O3' 121.0(2) yes O3' N' O1' 118.8(2) yes O1 N O2 122.7(2) yes O2 N O3 119.4(2) yes O3 N O1 117.90(14) yes H1 N1 C2 121.(2) no H1 N1 C6 116.(2) no H1' N1' C2' 119.5(14) no H1' N1' C6' 118.6(15) no H1a O1a C1 112.(2) no H1b O1b C1 114.(2) no H3 C3 C4 123.4(13) no H3 C3 C2 116.9(13) no H3' C3' C4' 122.1(13) no H3' C3' C2' 118.5(13) no H4 C4 C5 118.6(14) no H4 C4 C3 121.3(14) no H4' C4' C5' 120.6(15) no H4' C4' C3' 119.4(15) no H5 C5 C6 116.7(13) no H5 C5 C4 124.0(13) no H5' C5' C6' 120.(2) no H5' C5' C4' 120.(2) no H6 C6 N1 112.0(14) no H6 C6 C5 128.1(14) no H6' C6' N1' 113.9(14) no H6' C6' C5' 125.8(14) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C2 N1 1.335(2) yes C6 N1 1.346(2) yes C2' N1' 1.341(2) yes C6' N1' 1.342(2) yes C1 O1a 1.385(2) yes C1 O1b 1.394(2) yes C2 C1 1.534(2) yes C2' C1 1.527(2) yes C3 C2 1.364(2) yes C3' C2' 1.371(3) yes C4 C3 1.383(3) yes C4' C3' 1.374(3) yes C5 C4 1.369(3) yes C5' C4' 1.379(4) yes C6 C5 1.356(3) yes C6' C5' 1.356(3) yes O1' N' 1.228(3) yes O2' N' 1.226(2) yes O3' N' 1.246(2) yes O1 N 1.224(2) yes O2 N 1.220(2) yes O3 N 1.268(2) yes H1 N1 0.84(2) no H1' N1' 0.85(2) no H1a O1a 0.88(3) no H1b O1b 0.87(3) no H3 C3 0.88(2) no H3' C3' 0.94(3) no H4 C4 0.98(2) no H4' C4' 0.97(2) no H5 C5 0.95(2) no H5' C5' 0.91(2) no H6 C6 0.94(2) no H6' C6' 0.86(2) no 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 C2 C1 C2' N1' 114.6(2) yes C2' C1 C2 N1 120.0(2) yes O1a C1 C2 N1 -123.2(2) yes O1a C1 C2' N1' -5.9(2) yes O1b C1 C2 N1 1.5(2) yes O1b C1 C2' N1' -129.8(2) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139057422