#------------------------------------------------------------------------------ #$Date: 2025-08-19 15:49:58 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301806 $ #$URL: svn://www.crystallography.net/cod/cif/2/23/88/2238810.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_2238810 loop_ _publ_author_name 'Thirunavukkarasu, A.' 'Silambarasan, A.' 'Chakkaravarthi, G.' 'Mohankumar, R.' 'Umarani, P. R.' _publ_section_title ; 1H-Benzotriazole--4-hydroxybenzoic acid (1/1) ; _journal_coeditor_code VM2200 _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1605 _journal_paper_doi 10.1107/S1600536813026767 _journal_volume 69 _journal_year 2013 _chemical_formula_iupac 'C6 H5 N3, C7 H6 O3' _chemical_formula_moiety 'C6 H5 N3, C7 H6 O3' _chemical_formula_sum 'C13 H11 N3 O3' _chemical_formula_weight 257.25 _chemical_name_systematic ; 1H-Benzotriazole--4-hydroxybenzoic acid (1/1) ; _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 17.3634(13) _cell_length_b 11.4669(9) _cell_length_c 6.0818(4) _cell_measurement_reflns_used 2578 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 25.2 _cell_measurement_theta_min 2.1 _cell_volume 1210.91(15) _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_data_reduction 'SAINT (Bruker, 2004)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker Kappa APEXII CCD' _diffrn_measurement_method '\w and \f scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 6611 _diffrn_reflns_theta_full 26.83 _diffrn_reflns_theta_max 26.83 _diffrn_reflns_theta_min 2.13 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_T_max 0.9756 _exptl_absorpt_correction_T_min 0.9697 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 536 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _refine_diff_density_max 0.147 _refine_diff_density_min -0.112 _refine_ls_extinction_coef 0.025(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 2008)' _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 174 _refine_ls_number_reflns 2195 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.042 _refine_ls_R_factor_all 0.0374 _refine_ls_R_factor_gt 0.0307 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+0.0577P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0700 _refine_ls_wR_factor_ref 0.0740 _reflns_number_gt 1925 _reflns_number_total 2195 _reflns_threshold_expression I>2sigma(I) _iucr_refine_instructions_details ; TITL I in Pna2(1) CELL 0.71073 17.3634 11.4669 6.0818 90.000 90.000 90.000 ZERR 4.00 0.0013 0.0009 0.0004 0.000 0.000 0.000 LATT -1 SYMM - X, - Y, 1/2 + Z SYMM 1/2 - X, 1/2 + Y, 1/2 + Z SYMM 1/2 + X, 1/2 - Y, Z SFAC C H N O UNIT 52 44 12 12 MERG 2 FMAP 2 PLAN 20 SIZE 0.24 0.26 0.30 TEMP 22 ACTA BOND $H CONF HTAB N1 N2_$1 EQIV $1 -x,2-y,1/2+z HTAB O2 N3_$2 EQIV $2 1/2+x,3/2-y,1+z HTAB O3 O1_$3 EQIV $3 1/2-x,1/2+y,-1/2+z HTAB C13 O3_$4 EQIV $4 x,y,1+z L.S. 4 WGHT 0.036200 0.057700 EXTI 0.024955 FVAR 0.76048 C7 1 0.376685 0.744710 0.759394 11.00000 0.03660 0.03253 = 0.03979 -0.00201 0.00310 -0.00209 C4 1 0.324438 0.797945 0.598393 11.00000 0.03462 0.03379 = 0.03758 -0.00318 0.00218 -0.00220 C3 1 0.302444 0.737274 0.411223 11.00000 0.05094 0.03773 = 0.04847 -0.01186 -0.00507 0.00826 AFIX 43 H3 2 0.320365 0.661720 0.389488 11.00000 -1.20000 AFIX 0 C2 1 0.254820 0.786751 0.258057 11.00000 0.05748 0.04668 = 0.04342 -0.01858 -0.00934 0.00838 AFIX 43 H2 2 0.241636 0.745156 0.132296 11.00000 -1.20000 AFIX 0 C1 1 0.226181 0.897933 0.288711 11.00000 0.03914 0.04054 = 0.03587 -0.00290 -0.00007 0.00051 C6 1 0.246052 0.958907 0.476164 11.00000 0.04800 0.03026 = 0.04676 -0.00816 -0.00407 0.00286 AFIX 43 H6 2 0.226087 1.033121 0.499718 11.00000 -1.20000 AFIX 0 C5 1 0.295353 0.910329 0.628649 11.00000 0.04627 0.03749 = 0.04183 -0.01010 -0.00624 -0.00137 AFIX 43 H5 2 0.309337 0.952796 0.752657 11.00000 -1.20000 AFIX 0 N2 3 -0.009457 0.889525 0.249827 11.00000 0.05908 0.03513 = 0.04882 0.00166 -0.00697 -0.00286 C9 1 0.033832 0.726304 0.382396 11.00000 0.03794 0.03184 = 0.03358 -0.00331 -0.00011 -0.00298 C8 1 0.056157 0.813406 0.527981 11.00000 0.03966 0.03241 = 0.03763 -0.00526 0.00331 -0.00296 C13 1 0.097296 0.789679 0.719941 11.00000 0.05269 0.05384 = 0.03907 -0.01276 -0.00532 -0.00309 AFIX 43 H13 2 0.111745 0.848022 0.817823 11.00000 -1.20000 AFIX 0 C12 1 0.114902 0.675198 0.754438 11.00000 0.05626 0.06099 = 0.04446 0.00091 -0.01245 0.00524 AFIX 43 H12 2 0.141902 0.655070 0.880934 11.00000 -1.20000 AFIX 0 C11 1 0.093983 0.586528 0.607062 11.00000 0.05823 0.04052 = 0.05741 0.00230 -0.00912 0.00632 AFIX 43 H11 2 0.108304 0.510061 0.637487 11.00000 -1.20000 AFIX 0 C10 1 0.053466 0.609390 0.421580 11.00000 0.05240 0.03257 = 0.05279 -0.00737 -0.00565 -0.00062 AFIX 43 H10 2 0.039327 0.550376 0.324764 11.00000 -1.20000 AFIX 0 N3 3 -0.006499 0.777729 0.214586 11.00000 0.05190 0.03298 = 0.04056 -0.00036 -0.00580 -0.00219 N1 3 0.027924 0.911925 0.437660 11.00000 0.05869 0.02952 = 0.04859 -0.00855 -0.00088 -0.00427 AFIX 43 H1 2 0.033246 0.980348 0.493532 11.00000 -1.20000 AFIX 0 O1 4 0.389418 0.639691 0.771190 11.00000 0.05332 0.03226 = 0.05601 -0.00081 -0.00654 0.00038 O2 4 0.409728 0.819326 0.892512 11.00000 0.06299 0.03393 = 0.05422 -0.00361 -0.02209 0.00145 AFIX 83 H2A 2 0.438004 0.784263 0.977902 11.00000 -1.50000 AFIX 0 O3 4 0.179067 0.942457 0.132308 11.00000 0.06537 0.05088 = 0.04300 -0.00887 -0.01466 0.01448 AFIX 147 H3A 2 0.162668 1.005975 0.172855 11.00000 -1.50000 HKLF 4 REM I in Pna2(1) REM R1 = 0.0307 for 1925 Fo > 4sig(Fo) and 0.0374 for all 2195 data REM 174 parameters refined using 1 restraints END WGHT 0.0362 0.0577 REM Highest difference peak 0.147, deepest hole -0.112, 1-sigma level 0.029 Q1 1 0.0662 0.7736 0.4182 11.00000 0.05 0.15 Q2 1 0.3086 0.8364 0.6236 11.00000 0.05 0.13 Q3 1 0.3685 0.7843 0.6223 11.00000 0.05 0.13 Q4 1 0.3300 0.8610 0.5914 11.00000 0.05 0.12 Q5 1 -0.0371 0.7380 0.1386 11.00000 0.05 0.12 Q6 1 0.2466 0.7483 0.3839 11.00000 0.05 0.11 Q7 1 0.3585 0.6770 0.7846 11.00000 0.05 0.11 Q8 1 0.3432 0.7813 0.6912 11.00000 0.05 0.11 Q9 1 0.3909 0.8942 0.8974 11.00000 0.05 0.11 Q10 1 0.0351 0.6791 0.3936 11.00000 0.05 0.11 Q11 1 0.0316 0.7505 0.4945 11.00000 0.05 0.11 Q12 1 0.2598 0.9403 0.3466 11.00000 0.05 0.11 Q13 1 0.2157 0.8227 0.3109 11.00000 0.05 0.10 Q14 1 0.2985 0.7829 0.3024 11.00000 0.05 0.10 Q15 1 0.3248 0.7840 0.5088 11.00000 0.05 0.10 Q16 1 0.0111 0.5603 0.4160 11.00000 0.05 0.09 Q17 1 0.3696 0.7818 0.8941 11.00000 0.05 0.09 Q18 1 0.1875 0.6745 0.1634 11.00000 0.05 0.09 Q19 1 0.0662 0.8021 0.6156 11.00000 0.05 0.09 Q20 1 0.1606 0.8453 0.7666 11.00000 0.05 0.09 ; _cod_data_source_file vm2200.cif _cod_data_source_block I _cod_database_code 2238810 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' loop_ _atom_site_type_symbol _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_symmetry_multiplicity C C7 0.37669(8) 0.74471(13) 0.7594(3) 0.0363(4) Uani d . 1 1 C C4 0.32444(9) 0.79794(14) 0.5984(3) 0.0353(4) Uani d . 1 1 C C3 0.30244(10) 0.73727(15) 0.4112(3) 0.0457(4) Uani d . 1 1 H H3 0.3204 0.6617 0.3895 0.055 Uiso calc R 1 1 C C2 0.25482(10) 0.78675(16) 0.2581(3) 0.0492(5) Uani d . 1 1 H H2 0.2416 0.7452 0.1323 0.059 Uiso calc R 1 1 C C1 0.22618(9) 0.89793(15) 0.2887(3) 0.0385(4) Uani d . 1 1 C C6 0.24605(9) 0.95891(15) 0.4762(3) 0.0417(4) Uani d . 1 1 H H6 0.2261 1.0331 0.4997 0.050 Uiso calc R 1 1 C C5 0.29535(10) 0.91033(14) 0.6286(3) 0.0419(4) Uani d . 1 1 H H5 0.3093 0.9528 0.7527 0.050 Uiso calc R 1 1 N N2 -0.00946(8) 0.88952(13) 0.2498(3) 0.0477(4) Uani d . 1 1 C C9 0.03383(9) 0.72630(14) 0.3824(3) 0.0345(4) Uani d . 1 1 C C8 0.05616(10) 0.81341(14) 0.5280(3) 0.0366(4) Uani d . 1 1 C C13 0.09730(10) 0.78968(17) 0.7199(3) 0.0485(5) Uani d . 1 1 H H13 0.1117 0.8480 0.8178 0.058 Uiso calc R 1 1 C C12 0.11490(10) 0.67520(17) 0.7544(4) 0.0539(5) Uani d . 1 1 H H12 0.1419 0.6551 0.8809 0.065 Uiso calc R 1 1 C C11 0.09398(12) 0.58653(16) 0.6071(3) 0.0521(5) Uani d . 1 1 H H11 0.1083 0.5101 0.6375 0.062 Uiso calc R 1 1 C C10 0.05347(10) 0.60939(14) 0.4216(3) 0.0459(4) Uani d . 1 1 H H10 0.0393 0.5504 0.3248 0.055 Uiso calc R 1 1 N N3 -0.00650(8) 0.77773(12) 0.2146(2) 0.0418(3) Uani d . 1 1 N N1 0.02792(8) 0.91193(12) 0.4377(3) 0.0456(4) Uani d . 1 1 H H1 0.0332 0.9803 0.4935 0.055 Uiso calc R 1 1 O O1 0.38942(6) 0.63969(10) 0.7712(2) 0.0472(3) Uani d . 1 1 O O2 0.40973(7) 0.81933(10) 0.8925(2) 0.0504(3) Uani d . 1 1 H H2A 0.4380 0.7843 0.9779 0.076 Uiso calc R 1 1 O O3 0.17907(8) 0.94246(11) 0.13231(19) 0.0531(4) Uani d . 1 1 H H3A 0.1627 1.0060 0.1729 0.080 Uiso calc R 1 1 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 C7 0.0366(8) 0.0325(9) 0.0398(9) -0.0021(6) 0.0031(7) -0.0020(9) C4 0.0346(8) 0.0338(8) 0.0376(9) -0.0022(6) 0.0022(7) -0.0032(7) C3 0.0509(10) 0.0377(9) 0.0485(11) 0.0083(7) -0.0051(9) -0.0119(10) C2 0.0575(10) 0.0467(10) 0.0434(11) 0.0084(8) -0.0093(10) -0.0186(9) C1 0.0391(8) 0.0405(9) 0.0359(9) 0.0005(7) -0.0001(7) -0.0029(8) C6 0.0480(9) 0.0303(8) 0.0468(10) 0.0029(7) -0.0041(8) -0.0082(7) C5 0.0463(9) 0.0375(9) 0.0418(10) -0.0014(7) -0.0062(8) -0.0101(8) N2 0.0591(9) 0.0351(8) 0.0488(9) -0.0029(6) -0.0070(8) 0.0017(7) C9 0.0379(8) 0.0318(8) 0.0336(9) -0.0030(6) -0.0001(7) -0.0033(7) C8 0.0397(9) 0.0324(9) 0.0376(9) -0.0030(7) 0.0033(7) -0.0053(7) C13 0.0527(10) 0.0538(12) 0.0391(10) -0.0031(8) -0.0053(8) -0.0128(10) C12 0.0563(11) 0.0610(12) 0.0445(11) 0.0052(9) -0.0124(10) 0.0009(11) C11 0.0582(11) 0.0405(11) 0.0574(12) 0.0063(8) -0.0091(10) 0.0023(10) C10 0.0524(10) 0.0326(9) 0.0528(12) -0.0006(7) -0.0056(10) -0.0074(9) N3 0.0519(8) 0.0330(8) 0.0406(8) -0.0022(6) -0.0058(7) -0.0004(7) N1 0.0587(9) 0.0295(7) 0.0486(9) -0.0043(6) -0.0009(8) -0.0086(7) O1 0.0533(7) 0.0323(7) 0.0560(8) 0.0004(5) -0.0065(6) -0.0008(7) O2 0.0630(7) 0.0339(7) 0.0542(8) 0.0015(5) -0.0221(7) -0.0036(6) O3 0.0654(8) 0.0509(8) 0.0430(7) 0.0145(6) -0.0147(6) -0.0089(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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 O1 C7 O2 121.74(15) O1 C7 C4 123.97(15) O2 C7 C4 114.28(13) C3 C4 C5 118.12(15) C3 C4 C7 120.59(15) C5 C4 C7 121.30(15) C2 C3 C4 121.11(16) C2 C3 H3 119.4 C4 C3 H3 119.4 C3 C2 C1 120.55(16) C3 C2 H2 119.7 C1 C2 H2 119.7 O3 C1 C2 118.07(15) O3 C1 C6 122.67(15) C2 C1 C6 119.26(16) C5 C6 C1 120.36(15) C5 C6 H6 119.8 C1 C6 H6 119.8 C6 C5 C4 120.56(15) C6 C5 H5 119.7 C4 C5 H5 119.7 N3 N2 N1 108.09(14) N3 C9 C8 107.91(14) N3 C9 C10 131.39(15) C8 C9 C10 120.69(16) N1 C8 C9 103.95(15) N1 C8 C13 133.65(17) C9 C8 C13 122.39(16) C12 C13 C8 115.53(17) C12 C13 H13 122.2 C8 C13 H13 122.2 C13 C12 C11 122.75(19) C13 C12 H12 118.6 C11 C12 H12 118.6 C10 C11 C12 121.73(17) C10 C11 H11 119.1 C12 C11 H11 119.1 C11 C10 C9 116.89(16) C11 C10 H10 121.6 C9 C10 H10 121.6 N2 N3 C9 108.75(14) N2 N1 C8 111.29(14) N2 N1 H1 124.4 C8 N1 H1 124.4 C7 O2 H2A 109.5 C1 O3 H3A 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C7 O1 1.2265(18) C7 O2 1.3102(19) C7 C4 1.468(2) C4 C3 1.388(2) C4 C5 1.396(2) C3 C2 1.369(2) C3 H3 0.9300 C2 C1 1.381(2) C2 H2 0.9300 C1 O3 1.3545(19) C1 C6 1.381(2) C6 C5 1.380(2) C6 H6 0.9300 C5 H5 0.9300 N2 N3 1.3008(19) N2 N1 1.339(2) C9 N3 1.371(2) C9 C8 1.390(2) C9 C10 1.404(2) C8 N1 1.348(2) C8 C13 1.395(3) C13 C12 1.364(3) C13 H13 0.9300 C12 C11 1.403(3) C12 H12 0.9300 C11 C10 1.355(3) C11 H11 0.9300 C10 H10 0.9300 N1 H1 0.8600 O2 H2A 0.8200 O3 H3A 0.8200 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 N2 2_575 0.86 2.20 2.982(2) 152 y O2 H2A N3 4_566 0.82 1.87 2.6817(19) 169 y O3 H3A O1 3_554 0.82 1.88 2.6912(17) 171 y C13 H13 O3 1_556 0.93 2.49 3.373(2) 159 y 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 O1 C7 C4 C3 -18.0(2) O2 C7 C4 C3 161.82(15) O1 C7 C4 C5 161.86(16) O2 C7 C4 C5 -18.3(2) C5 C4 C3 C2 1.3(3) C7 C4 C3 C2 -178.86(17) C4 C3 C2 C1 -1.3(3) C3 C2 C1 O3 -179.75(16) C3 C2 C1 C6 -0.1(3) O3 C1 C6 C5 -178.87(16) C2 C1 C6 C5 1.5(3) C1 C6 C5 C4 -1.5(3) C3 C4 C5 C6 0.1(2) C7 C4 C5 C6 -179.74(16) N3 C9 C8 N1 -0.18(17) C10 C9 C8 N1 179.72(16) N3 C9 C8 C13 178.84(16) C10 C9 C8 C13 -1.3(3) N1 C8 C13 C12 179.32(19) C9 C8 C13 C12 0.6(3) C8 C13 C12 C11 0.6(3) C13 C12 C11 C10 -1.2(3) C12 C11 C10 C9 0.5(3) N3 C9 C10 C11 -179.47(17) C8 C9 C10 C11 0.6(2) N1 N2 N3 C9 -0.20(18) C8 C9 N3 N2 0.25(18) C10 C9 N3 N2 -179.65(18) N3 N2 N1 C8 0.09(19) C9 C8 N1 N2 0.06(18) C13 C8 N1 N2 -178.79(18) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139086172