#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/05/2200572.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_2200572 loop_ _publ_author_name 'Mahmoudkhani, Amir H.' 'Langer, Vratislav' _publ_section_title ; Two-dimensional hydrogen-bonded arrays in p-phenylazoanilinium oxalate ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o898 _journal_page_last o900 _journal_paper_doi 10.1107/S1600536801013885 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac '2C12 H12 N3 1+, C2 O4 2-' _chemical_formula_moiety '2C12 H12 N3 1+, C2 O4 2-' _chemical_formula_sum 'C26 H24 N6 O4' _chemical_formula_weight 484.51 _chemical_name_systematic ; Bis(p-phenylazoanilinium) oxalate ; _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 SHELXTL _cell_angle_alpha 92.0440(10) _cell_angle_beta 100.0450(10) _cell_angle_gamma 112.9550(10) _cell_formula_units_Z 1 _cell_length_a 6.48750(10) _cell_length_b 7.01510(10) _cell_length_c 14.29910(10) _cell_measurement_reflns_used 5443 _cell_measurement_temperature 297(2) _cell_measurement_theta_max 30 _cell_measurement_theta_min 1 _cell_volume 586.169(14) _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_collection 'SMART (Siemens, 1995)' _computing_data_reduction 'SAINT and SADABS (Sheldrick, 1996)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2000)' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Bruker, 2001)' _diffrn_ambient_temperature 297(2) _diffrn_detector_area_resol_mean no _diffrn_measured_fraction_theta_full .980 _diffrn_measured_fraction_theta_max .980 _diffrn_measurement_device_type 'Siemens 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 .023 _diffrn_reflns_av_sigmaI/netI .031 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 7891 _diffrn_reflns_theta_full 30.5 _diffrn_reflns_theta_max 30.5 _diffrn_reflns_theta_min 2.9 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time no _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .096 _exptl_absorpt_correction_T_max .976 _exptl_absorpt_correction_T_min .910 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour yellow-orange _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 254 _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid .50 _exptl_crystal_size_min .25 _refine_diff_density_max .32 _refine_diff_density_min -.22 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 211 _refine_ls_number_reflns 3499 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.04 _refine_ls_R_factor_all .052 _refine_ls_R_factor_gt .041 _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^)+(0.0677P)^2^+0.0807P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .129 _reflns_number_gt 2858 _reflns_number_total 3499 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ya6039.cif _cod_data_source_block I _cod_original_cell_volume 586.169(13) _cod_database_code 2200572 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 O1 .58318(11) .76598(10) .48700(5) .03369(18) Uani d . 1 . . O N1 -.14184(16) .74518(16) .04159(7) .0394(2) Uani d . 1 . . N C1 .08350(15) .79559(15) .33855(7) .0286(2) Uani d . 1 . . C O2 .79716(11) .58262(12) .52064(6) .0380(2) Uani d . 1 . . O N2 -.32444(17) .76653(17) .01430(7) .0407(2) Uani d . 1 . . N C2 -.11676(17) .82239(17) .30468(8) .0344(2) Uani d . 1 . . C H2 -.199(2) .854(2) .3535(11) .050(4) Uiso d . 1 . . H N3 .16503(14) .81488(13) .44204(6) .02889(18) Uani d D 1 . . N H33 .047(2) .746(2) .4699(10) .049(4) Uiso d D 1 . . H C3 -.19630(18) .80539(18) .20688(8) .0361(2) Uani d . 1 . . C H3 -.339(2) .822(2) .1802(10) .046(4) Uiso d . 1 . . H C4 -.07316(17) .76438(16) .14373(7) .0337(2) Uani d . 1 . . C C5 .12801(19) .73936(19) .17838(8) .0388(2) Uani d . 1 . . C H5 .214(3) .705(2) .1317(11) .052(4) Uiso d . 1 . . H C6 .20651(17) .75391(18) .27639(8) .0358(2) Uani d . 1 . . C H6 .343(3) .734(2) .3013(11) .055(4) Uiso d . 1 . . H C7 -.39778(18) .74820(17) -.08718(7) .0356(2) Uani d . 1 . . C C8 -.6040(2) .7661(2) -.11869(8) .0421(3) Uani d . 1 . . C H8 -.686(3) .793(3) -.0683(12) .058(4) Uiso d . 1 . . H C9 -.6907(2) .7481(2) -.21620(9) .0444(3) Uani d . 1 . . C H9 -.837(3) .759(3) -.2406(12) .060(4) Uiso d . 1 . . H C10 -.5701(2) .7156(2) -.28159(9) .0445(3) Uani d . 1 . . C H10 -.635(3) .701(3) -.3485(13) .065(5) Uiso d . 1 . . H C11 -.3627(2) .6996(2) -.24997(9) .0453(3) Uani d . 1 . . C H11 -.276(3) .677(3) -.2974(13) .063(5) Uiso d . 1 . . H C12 -.2759(2) .71477(19) -.15315(8) .0411(3) Uani d . 1 . . C H12 -.132(3) .702(3) -.1313(11) .055(4) Uiso d . 1 . . H C13 .61097(14) .60138(14) .50227(6) .02527(18) Uani d . 1 . . C H32 .235(2) .9518(19) .4666(9) .038(3) Uiso d D 1 . . H H31 .277(2) .763(2) .4568(11) .051(4) 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 O1 .0299(3) .0251(3) .0444(4) .0099(3) .0057(3) .0056(3) N1 .0395(5) .0458(5) .0341(5) .0191(4) .0059(4) .0054(4) C1 .0251(4) .0252(4) .0332(5) .0083(3) .0043(3) .0049(3) O2 .0234(3) .0375(4) .0539(5) .0118(3) .0094(3) .0135(3) N2 .0415(5) .0497(6) .0328(5) .0212(4) .0049(4) .0056(4) C2 .0296(4) .0421(5) .0352(5) .0178(4) .0073(4) .0068(4) N3 .0249(4) .0275(4) .0328(4) .0098(3) .0038(3) .0044(3) C3 .0302(5) .0437(6) .0368(5) .0181(4) .0048(4) .0073(4) C4 .0332(5) .0339(5) .0330(5) .0131(4) .0051(4) .0051(4) C5 .0358(5) .0468(6) .0382(5) .0207(5) .0093(4) .0037(5) C6 .0295(4) .0428(6) .0385(5) .0188(4) .0054(4) .0049(4) C7 .0381(5) .0359(5) .0317(5) .0148(4) .0051(4) .0037(4) C8 .0423(6) .0491(7) .0384(6) .0224(5) .0072(4) .0053(5) C9 .0440(6) .0461(6) .0420(6) .0204(5) .0005(5) .0060(5) C10 .0543(7) .0409(6) .0328(5) .0163(5) .0022(5) .0032(4) C11 .0525(7) .0480(7) .0362(6) .0204(5) .0113(5) .0023(5) C12 .0404(6) .0451(6) .0388(6) .0186(5) .0075(4) .0035(5) C13 .0240(4) .0259(4) .0244(4) .0084(3) .0050(3) .0031(3) 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_3 _geom_angle _geom_angle_publ_flag N2 N1 C4 . 113.51(9) yes C6 C1 C2 . 121.26(9) ? C6 C1 N3 . 120.11(8) ? C2 C1 N3 . 118.63(9) ? N1 N2 C7 . 114.92(9) yes C3 C2 C1 . 119.47(9) ? C3 C2 H2 . 122.7(8) ? C1 C2 H2 . 117.9(8) ? C1 N3 H33 . 109.7(10) ? C1 N3 H32 . 110.4(8) ? H33 N3 H32 . 111.0(13) ? C1 N3 H31 . 111.3(9) ? H33 N3 H31 . 109.5(13) ? H32 N3 H31 . 105.0(12) ? C2 C3 C4 . 119.70(9) ? C2 C3 H3 . 121.6(8) ? C4 C3 H3 . 118.7(8) ? C5 C4 C3 . 120.37(10) ? C5 C4 N1 . 116.09(9) ? C3 C4 N1 . 123.54(9) ? C6 C5 C4 . 119.99(10) ? C6 C5 H5 . 120.0(8) ? C4 C5 H5 . 119.9(8) ? C1 C6 C5 . 119.20(9) ? C1 C6 H6 . 119.8(10) ? C5 C6 H6 . 120.9(10) ? C8 C7 C12 . 120.27(10) ? C8 C7 N2 . 115.57(10) ? C12 C7 N2 . 124.16(10) ? C7 C8 C9 . 119.81(11) ? C7 C8 H8 . 117.7(9) ? C9 C8 H8 . 122.5(9) ? C10 C9 C8 . 120.02(11) ? C10 C9 H9 . 118.4(10) ? C8 C9 H9 . 121.6(10) ? C9 C10 C11 . 120.13(11) ? C9 C10 H10 . 118.4(10) ? C11 C10 H10 . 121.5(10) ? C12 C11 C10 . 120.42(11) ? C12 C11 H11 . 119.9(10) ? C10 C11 H11 . 119.7(10) ? C11 C12 C7 . 119.36(11) ? C11 C12 H12 . 120.2(9) ? C7 C12 H12 . 120.5(9) ? O2 C13 O1 . 126.67(8) yes O2 C13 C13 2_666 116.66(10) yes O1 C13 C13 2_666 116.66(9) yes 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 O1 C13 . 1.2571(11) yes N1 N2 . 1.2487(13) yes N1 C4 . 1.4359(13) yes C1 C2 . 1.3911(13) ? C1 C6 . 1.3868(14) ? C1 N3 . 1.4645(12) yes O2 C13 . 1.2494(11) yes N2 C7 . 1.4306(14) yes C2 C3 . 1.3873(15) ? C2 H2 . 1.020(10) ? N3 H33 . .900(10) ? N3 H32 . .910(10) ? N3 H31 . .930(10) ? C3 C4 . 1.3960(15) ? C3 H3 . .990(10) ? C4 C5 . 1.3924(15) ? C5 C6 . 1.3908(15) ? C5 H5 . 1.020(10) ? C6 H6 . .960(10) ? C7 C8 . 1.3906(16) ? C7 C12 . 1.3995(16) ? C8 C9 . 1.3911(17) ? C8 H8 . 1.020(10) ? C9 C10 . 1.3848(19) ? C9 H9 . .98(2) ? C10 C11 . 1.3915(18) ? C10 H10 . .96(2) ? C11 C12 . 1.3843(16) ? C11 H11 . .99(2) ? C12 H12 . .97(2) ? C13 C13 2_666 1.5698(17) yes 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 (a)N3 H31 O1 . .930(10) 1.950(10) 2.8325(15) 158.0(14) (b)N3 H31 O2 2_666 .930(10) 2.330(10) 2.9520(12) 124.4(12) (c)N3 H32 O1 2_676 .910(10) 1.890(10) 2.7939(11) 172.0(12) (d)N3 H33 O2 1_455 .900(10) 1.880(10) 2.7654(11) 175.3(15) (e)C2 H2 O1 1_455 1.020(10) 2.520(10) 3.4620(13) 153.3(12) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139064958