#------------------------------------------------------------------------------ #$Date: 2016-02-20 03:06:23 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/04/2200412.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_2200412 loop_ _publ_author_name 'Cowan, John A.' 'Howard, Judith A. K.' 'Leech, Michael A.' 'Williams, Ian D.' _publ_section_title ; Bis(4-aminopyridinium) 2,5-dioxidobenzoquinone dihydrate ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o563 _journal_page_last o565 _journal_paper_doi 10.1107/S1600536801009011 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac '2C5 H7 N2 1+, C6 H2 O4 2-, 2H2 O' _chemical_formula_moiety '2C5 H7 N2 1+, C6 H2 O4 2-, 2H2 O' _chemical_formula_sum 'C16 H20 N4 O6' _chemical_formula_weight 364.36 _chemical_name_systematic ; Bis(4-aminopyridinium) 2,5-dioxidobenzoquinone dihydrate ; _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' _cell_angle_alpha 90.00 _cell_angle_beta 95.684(16) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 6.345(4) _cell_length_b 11.353(8) _cell_length_c 11.838(8) _cell_measurement_reflns_used 980 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 23.85 _cell_measurement_theta_min 4.99 _cell_volume 848.6(10) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full .995 _diffrn_measured_fraction_theta_max .995 _diffrn_measurement_device_type 'Bruker SMART-CCD' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0548 _diffrn_reflns_av_sigmaI/netI .0404 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 7323 _diffrn_reflns_theta_full 27.10 _diffrn_reflns_theta_max 27.10 _diffrn_reflns_theta_min 2.49 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .111 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min .804 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 384 _exptl_crystal_size_max .65 _exptl_crystal_size_mid .35 _exptl_crystal_size_min .05 _refine_diff_density_max .288 _refine_diff_density_min -.377 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.659 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 158 _refine_ls_number_reflns 1861 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.659 _refine_ls_R_factor_all .0919 _refine_ls_R_factor_gt .0680 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.05P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1482 _reflns_number_gt 1475 _reflns_number_total 1861 _reflns_threshold_expression I>2\s(I) _cod_data_source_file cf6075.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_cell_volume 848.5(10) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2200412 _cod_database_fobs_code 2200412 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_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 1.8229(3) -.06776(18) .94682(19) .0160(5) Uani d . 1 . . C O1 1.6626(3) -.11905(13) .89569(14) .0200(4) Uani d . 1 . . O C2 1.8462(4) .06544(19) .92583(18) .0153(5) Uani d . 1 . . C O2 1.6999(2) .11425(13) .86112(14) .0186(4) Uani d . 1 . . O C3 2.0225(4) .12489(19) .9788(2) .0181(5) Uani d . 1 . . C H3 2.039(4) .210(2) .969(2) .017(6) Uiso d . 1 . . H N1 1.3352(3) .00917(17) .76266(18) .0191(5) Uani d . 1 . . N H1 1.475(5) .009(2) .800(3) .039(9) Uiso d . 1 . . H C11 1.2239(4) -.0928(2) .7516(2) .0207(5) Uani d . 1 . . C H11 1.296(4) -.161(2) .784(2) .019(6) Uiso d . 1 . . H C12 1.0248(4) -.09632(18) .69516(19) .0175(5) Uani d . 1 . . C H12 .950(4) -.168(2) .689(2) .027(7) Uiso d . 1 . . H C13 .9301(4) .00777(18) .64651(19) .0152(5) Uani d . 1 . . C N2 .7376(3) .00589(18) .58957(17) .0197(5) Uani d . 1 . . N H2A .679(4) .074(2) .554(2) .022(7) Uiso d . 1 . . H H2B .659(4) -.064(2) .574(2) .021(7) Uiso d . 1 . . H C14 1.0523(4) .11252(19) .6605(2) .0172(5) Uani d . 1 . . C H14 .993(4) .178(2) .630(2) .019(6) Uiso d . 1 . . H C15 1.2494(4) .1106(2) .7176(2) .0194(5) Uani d . 1 . . C H15 1.336(4) .179(3) .733(2) .031(7) Uiso d . 1 . . H O10 .5121(3) .20783(14) .47749(16) .0212(4) Uani d . 1 . . O H10A .435(5) .261(3) .520(3) .048(10) Uiso d . 1 . . H H10B .570(6) .254(3) .426(3) .051(10) Uiso 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 .0134(12) .0178(11) .0172(12) .0000(9) .0042(10) -.0038(9) O1 .0178(9) .0188(8) .0227(9) -.0013(6) -.0020(7) -.0004(7) C2 .0167(12) .0186(11) .0113(11) .0028(9) .0043(9) .0000(8) O2 .0156(9) .0187(8) .0209(9) .0024(6) -.0013(7) .0013(6) C3 .0216(13) .0132(10) .0193(12) -.0010(9) .0012(10) .0002(9) N1 .0121(10) .0259(10) .0188(10) .0004(8) -.0008(8) -.0028(8) C11 .0222(13) .0217(11) .0189(12) .0049(10) .0046(10) .0002(10) C12 .0197(12) .0133(10) .0195(13) -.0007(9) .0027(10) -.0012(9) C13 .0153(11) .0203(11) .0112(11) .0007(9) .0068(9) -.0014(9) N2 .0185(10) .0200(10) .0196(11) .0005(8) -.0035(8) -.0009(8) C14 .0204(13) .0152(11) .0163(12) .0008(9) .0039(10) .0029(9) C15 .0203(13) .0200(11) .0183(12) -.0048(9) .0039(10) -.0014(9) O10 .0200(9) .0161(8) .0275(10) .0000(7) .0021(8) .0017(7) 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' N N .0061 .0033 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle O1 C1 C3 . 3_957 124.1(2) O1 C1 C2 . . 117.1(2) C3 C1 C2 3_957 . 118.8(2) O2 C2 C3 . . 124.2(2) O2 C2 C1 . . 116.7(2) C3 C2 C1 . . 119.1(2) C2 C3 C1 . 3_957 122.1(2) C2 C3 H3 . . 121.4(16) C1 C3 H3 3_957 . 116.5(17) C11 N1 C15 . . 120.3(2) C11 N1 H1 . . 119(2) C15 N1 H1 . . 120(2) N1 C11 C12 . . 121.1(2) N1 C11 H11 . . 115.6(18) C12 C11 H11 . . 123.2(18) C11 C12 C13 . . 120.3(2) C11 C12 H12 . . 118.7(18) C13 C12 H12 . . 121.0(18) N2 C13 C12 . . 121.3(2) N2 C13 C14 . . 122.3(2) C12 C13 C14 . . 116.5(2) C13 N2 H2A . . 120.6(17) C13 N2 H2B . . 123.4(18) H2A N2 H2B . . 116(2) C15 C14 C13 . . 120.6(2) C15 C14 H14 . . 121.2(18) C13 C14 H14 . . 118.3(18) N1 C15 C14 . . 121.2(2) N1 C15 H15 . . 115.4(18) C14 C15 H15 . . 123.4(18) H10A O10 H10B . . 106(3) 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 O1 . 1.272(3) ? C1 C3 3_957 1.409(4) ? C1 C2 . 1.542(3) ? C2 O2 . 1.271(3) ? C2 C3 . 1.403(4) ? C3 C1 3_957 1.409(4) ? C3 H3 . .96(3) ? N1 C11 . 1.354(3) ? N1 C15 . 1.357(3) ? N1 H1 . .93(3) ? C11 C12 . 1.371(4) ? C11 H11 . .97(3) ? C12 C13 . 1.420(3) ? C12 H12 . .96(3) ? C13 N2 . 1.337(3) ? C13 C14 . 1.421(3) ? N2 H2A . .94(3) ? N2 H2B . .93(3) ? C14 C15 . 1.361(4) ? C14 H14 . .91(3) ? C15 H15 . .94(3) ? O10 H10A . .91(4) ? O10 H10B . .91(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 N1 H1 O1 . .95(3) 2.14(3) 2.875(3) 133(2) y N1 H1 O2 . .95(3) 1.94(3) 2.757(3) 142(2) y C11 H11 O1 . .96(3) 2.60(3) 3.132(4) 115(2) y C15 H15 O2 . .96(3) 2.74(3) 3.177(3) 109(2) y N2 H2A O10 . .94(3) 2.02(3) 2.948(3) 172(2) y N2 H2B O10 3_656 .94(3) 2.02(3) 2.963(3) 174(2) y O10 H10A O1 2_756 .95(4) 1.83(4) 2.770(3) 168(3) y O10 H10B O2 4_465 .91(4) 1.90(4) 2.779(3) 161(3) y