#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/23/2012360.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_2012360 loop_ _publ_author_name 'Lyakhov, Alexander S.' 'Gaponik, Pavel N.' 'Voitekhovich, Sergei V.' 'Ivashkevich, Ludmila S.' 'Kulak, Alexander A.' 'Ivashkevich, Oleg A.' _publ_section_title ; 2-(1H-Tetrazol-1-yl)benzoic acid ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1436 _journal_page_last 1437 _journal_paper_doi 10.1107/S0108270101016006 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C8 H6 N4 O2' _chemical_formula_moiety 'C8 H6 N4 O2' _chemical_formula_sum 'C8 H6 N4 O2' _chemical_formula_weight 190.17 _chemical_name_systematic ; 2-(1H-Tetrazol-1-yl)benzoic acid ; _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' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 91.15(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 3.8410(10) _cell_length_b 16.073(4) _cell_length_c 13.234(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.1 _cell_measurement_theta_min 17.9 _cell_volume 816.9(3) _computing_cell_refinement 'R3m Software' _computing_data_collection 'R3m Software (Nicolet, 1980)' _computing_data_reduction 'R3m Software' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1999)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Nicolet R3m four-circle' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71069 _diffrn_reflns_av_R_equivalents .0188 _diffrn_reflns_av_sigmaI/netI .0235 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 2822 _diffrn_reflns_theta_full 30.08 _diffrn_reflns_theta_max 30.08 _diffrn_reflns_theta_min 1.99 _diffrn_standards_decay_% 2.2 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .117 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.546 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 392 _exptl_crystal_size_max .74 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .18 _refine_diff_density_max .259 _refine_diff_density_min -.157 _refine_ls_extinction_coef .077(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 152 _refine_ls_number_reflns 2410 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all .0474 _refine_ls_R_factor_gt .0377 _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^)+(0.0582P)^2^+0.1169P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .1029 _refine_ls_wR_factor_ref .1126 _reflns_number_gt 1888 _reflns_number_total 2410 _reflns_threshold_expression I>2\s(I) _cod_data_source_file av1091.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2012360 _cod_database_fobs_code 2012360 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 N1 .7659(2) .11787(5) .37068(6) .0325(2) Uani d . 1 . . N N2 .9448(3) .10356(6) .45845(7) .0444(3) Uani d . 1 . . N N3 .9235(3) .17065(7) .51131(8) .0476(3) Uani d . 1 . . N N4 .7335(3) .22903(6) .46038(7) .0423(2) Uani d . 1 . . N C5 .6410(3) .19511(7) .37417(9) .0393(3) Uani d . 1 . . C H5 .516(4) .2200(10) .3189(13) .056(4) Uiso d . 1 . . H C6 .7118(3) .05210(6) .29889(7) .0311(2) Uani d . 1 . . C C7 .7803(3) .06150(6) .19593(7) .0302(2) Uani d . 1 . . C C8 .7050(3) -.00590(7) .13267(8) .0370(2) Uani d . 1 . . C H8 .747(4) -.0004(9) .0594(13) .053(4) Uiso d . 1 . . H C9 .5729(3) -.07948(7) .17030(10) .0432(3) Uani d . 1 . . C H9 .518(4) -.1234(11) .1251(12) .057(4) Uiso d . 1 . . H C10 .5144(4) -.08788(7) .27227(10) .0451(3) Uani d . 1 . . C H10 .429(4) -.1382(11) .2960(12) .059(4) Uiso d . 1 . . H C11 .5800(3) -.02159(7) .33665(9) .0399(3) Uani d . 1 . . C H11 .548(4) -.0264(10) .4080(13) .058(4) Uiso d . 1 . . H C12 .9455(3) .13766(6) .15292(8) .0328(2) Uani d . 1 . . C O1 1.0738(3) .19278(5) .20294(6) .0468(2) Uani d . 1 . . O O2 .9448(3) .13685(6) .05348(6) .0568(3) Uani d . 1 . . O H2 1.036(5) .1855(13) .0298(16) .080(6) 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 N1 .0431(5) .0293(4) .0254(4) -.0005(3) .0045(3) .0000(3) N2 .0636(7) .0407(5) .0288(4) .0019(4) -.0024(4) .0009(4) N3 .0683(7) .0442(5) .0303(5) -.0023(5) .0001(4) -.0042(4) N4 .0557(6) .0367(5) .0347(5) -.0012(4) .0070(4) -.0071(4) C5 .0504(6) .0323(5) .0352(5) .0039(4) .0020(5) -.0046(4) C6 .0386(5) .0269(4) .0280(4) .0011(4) .0036(4) -.0013(3) C7 .0355(5) .0279(4) .0273(4) .0016(4) .0029(3) .0002(3) C8 .0439(6) .0364(5) .0308(5) .0007(4) .0036(4) -.0053(4) C9 .0521(7) .0317(5) .0458(6) -.0033(5) .0035(5) -.0092(4) C10 .0575(7) .0289(5) .0491(7) -.0063(5) .0073(5) .0009(4) C11 .0530(7) .0328(5) .0343(5) -.0042(5) .0082(5) .0030(4) C12 .0380(5) .0320(5) .0287(5) .0016(4) .0027(4) .0027(3) O1 .0646(6) .0407(5) .0351(4) -.0158(4) .0023(4) .0012(3) O2 .0951(8) .0477(5) .0276(4) -.0212(5) .0052(4) .0046(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 C5 N1 N2 107.74(9) C5 N1 C6 131.51(9) N2 N1 C6 120.42(9) N3 N2 N1 106.63(10) N2 N3 N4 110.35(10) C5 N4 N3 106.18(10) N4 C5 N1 109.10(10) N4 C5 H5 128.1(9) N1 C5 H5 122.7(10) C11 C6 C7 121.34(9) C11 C6 N1 116.14(9) C7 C6 N1 122.50(9) C8 C7 C6 117.31(9) C8 C7 C12 119.41(9) C6 C7 C12 123.19(9) C9 C8 C7 121.37(10) C9 C8 H8 119.8(9) C7 C8 H8 118.8(9) C10 C9 C8 120.27(10) C10 C9 H9 120.4(10) C8 C9 H9 119.3(10) C9 C10 C11 119.71(11) C9 C10 H10 118.7(10) C11 C10 H10 121.6(10) C10 C11 C6 119.96(10) C10 C11 H11 121.3(9) C6 C11 H11 118.6(9) O1 C12 O2 123.30(10) O1 C12 C7 124.34(10) O2 C12 C7 112.33(9) C12 O2 H2 109.9(13) 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 N1 C5 . 1.3320(10) yes N1 N2 . 1.3570(10) yes N1 C6 . 1.4340(10) yes N2 N3 . 1.2890(10) yes N3 N4 . 1.359(2) yes N4 C5 . 1.307(2) yes C5 H5 . .956(16) ? C6 C11 . 1.3853(14) ? C6 C7 . 1.4012(13) ? C7 C8 . 1.3958(14) ? C7 C12 . 1.4960(10) yes C8 C9 . 1.3835(16) ? C8 H8 . .991(17) ? C9 C10 . 1.3792(18) ? C9 H9 . .947(17) ? C10 C11 . 1.3842(16) ? C10 H10 . .930(17) ? C11 H11 . .958(18) ? C12 O1 . 1.2050(10) yes C12 O2 . 1.3160(10) yes O2 H2 . .92(2) ? 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 O2 H2 N4 4_665 .92(2) 1.83(2) 2.7290(10) 169(2) C5 H5 O1 1_455 .96(2) 2.31(2) 3.112(2) 141.0(10) 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 C5 N1 N2 N3 .09(13) C6 N1 N2 N3 -174.01(9) N1 N2 N3 N4 .11(14) N2 N3 N4 C5 -.28(14) N3 N4 C5 N1 .33(14) N2 N1 C5 N4 -.27(14) C6 N1 C5 N4 172.94(10) C5 N1 C6 C11 -122.17(13) N2 N1 C6 C11 50.32(14) C5 N1 C6 C7 56.55(16) N2 N1 C6 C7 -130.95(11) C11 C6 C7 C8 1.04(16) N1 C6 C7 C8 -177.62(10) C11 C6 C7 C12 -175.62(10) N1 C6 C7 C12 5.72(15) C6 C7 C8 C9 -.94(16) C12 C7 C8 C9 175.84(11) C7 C8 C9 C10 -.38(19) C8 C9 C10 C11 1.6(2) C9 C10 C11 C6 -1.5(2) C7 C6 C11 C10 .19(18) N1 C6 C11 C10 178.93(11) C8 C7 C12 O1 -166.81(11) C6 C7 C12 O1 9.77(17) C8 C7 C12 O2 11.29(14) C6 C7 C12 O2 -172.12(10) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 659042 2 PubChem 753608