#------------------------------------------------------------------------------ #$Date: 2022-03-29 11:07:42 +0300 (Tue, 29 Mar 2022) $ #$Revision: 274072 $ #$URL: file:///home/coder/svn-repositories/cod/cif/8/10/49/8104918.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_8104918 loop_ _publ_author_name 'Hosten, Eric C.' 'Betz, Richard' _publ_section_title ; The crystal structure of 3-ammonio-4-aminobenzoate, C7H8N2O2 -- a second polymorph ; _journal_issue 1 _journal_name_full 'Zeitschrift f\"ur Kristallographie - New Crystal Structures' _journal_page_first 187 _journal_page_last 188 _journal_paper_doi 10.1515/ncrs-2020-0510 _journal_volume 236 _journal_year 2021 _chemical_formula_moiety 'C7 H8 N2 O2' _chemical_formula_sum 'C7 H8 N2 O2' _chemical_formula_weight 152.15 _chemical_name_common 3-ammonio-4-aminobenzoate _chemical_name_systematic 3-ammonio-4-aminobenzoate _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary SHELXS _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 95.400(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.9884(6) _cell_length_b 6.0490(4) _cell_length_c 12.1290(8) _cell_measurement_reflns_used 2675 _cell_measurement_temperature 200(2) _cell_measurement_theta_max 27.82 _cell_measurement_theta_min 2.70 _cell_volume 656.54(8) _computing_cell_refinement 'SAINT [1]' _computing_data_collection 'APEX2 [1]' _computing_data_reduction 'SAINT [1]' _computing_molecular_graphics 'ORTEP3 [3], Mercury [4]' _computing_publication_material 'SHELXL-97 [2], PLATON [5]' _computing_structure_refinement 'SHELXL-97 [2]' _computing_structure_solution 'SHELXS-97 [2]' _diffrn_ambient_temperature 200(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_sigmaI/netI 0.8087 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 5578 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.061 _diffrn_reflns_theta_min 2.703 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.8087 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; SADABS [6] ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.539 _exptl_crystal_description platelet _exptl_crystal_F_000 320 _exptl_crystal_size_max 0.532 _exptl_crystal_size_mid 0.351 _exptl_crystal_size_min 0.106 _refine_diff_density_max 0.314 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.045 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 120 _refine_ls_number_reflns 1571 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0340 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0535P)^2^+0.2213P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0915 _refine_ls_wR_factor_ref 0.0978 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1295 _reflns_number_total 1571 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL fa118_s in P2(1)/n fa118.res created by SHELXL-2018/3 at 15:12:19 on 29-Aug-2020 CELL 0.71073 8.9884 6.0490 12.1290 90.000 95.400 90.000 ZERR 4 0.0006 0.0004 0.0008 0.000 0.002 0.000 LATT 1 SYMM 0.50000 - X , 0.50000 + Y , 0.50000 - Z SFAC C H N O UNIT 28 32 8 8 ACTA NOHKL BOND $H CONF HTAB TEMP -73 OMIT 0 0 2 EQIV $1 -x+1, -y, -z EQIV $2 -x+1, -y+1, -z EQIV $3 x-1/2, -y+1/2, z+1/2 EQIV $4 x-1/2, -y+3/2, z+1/2 HTAB N1 O2_$1 HTAB N1 O1_$2 HTAB N1 O1_$3 HTAB N1 O2_$3 HTAB N2 O2_$3 HTAB N2 O1_$4 MPLA C2 C3 C4 C5 C6 C7 MPLA C1 O1 O2 MPLA C1 C2 C3 C4 C5 C6 C7 N1 N2 L.S. 10 FMAP 2 PLAN -5 WGHT 0.053500 0.221300 FVAR 0.23861 O1 4 0.854071 0.417071 -0.110633 11.00000 0.02615 0.02258 = 0.02366 -0.00040 0.00965 -0.00291 O2 4 0.770740 0.082284 -0.070678 11.00000 0.03144 0.01887 = 0.02952 -0.00502 0.01060 -0.00205 N1 3 0.372159 0.259789 0.189432 11.00000 0.02000 0.01691 = 0.02382 -0.00257 0.00711 -0.00365 H711 2 0.348830 0.139642 0.145861 11.00000 0.03154 H712 2 0.291002 0.361362 0.174457 11.00000 0.03856 H713 2 0.374126 0.209925 0.269059 11.00000 0.04666 N2 3 0.470554 0.660687 0.290156 11.00000 0.02538 0.02125 = 0.02536 -0.00751 0.00801 -0.00250 H721 2 0.426076 0.567471 0.333735 11.00000 0.03504 H722 2 0.511417 0.781221 0.323416 11.00000 0.03451 C1 1 0.783455 0.285747 -0.052169 11.00000 0.01794 0.01986 = 0.01888 -0.00023 0.00221 0.00041 C2 1 0.708403 0.383751 0.041488 11.00000 0.01872 0.01608 = 0.01710 0.00097 0.00259 0.00064 C3 1 0.587975 0.273048 0.080423 11.00000 0.02046 0.01264 = 0.01863 -0.00049 0.00165 -0.00046 AFIX 43 H3 2 0.560296 0.131288 0.051671 11.00000 -1.20000 AFIX 0 C4 1 0.508620 0.366813 0.160112 11.00000 0.01647 0.01596 = 0.01825 0.00146 0.00228 -0.00135 C5 1 0.550613 0.569408 0.209835 11.00000 0.01737 0.01639 = 0.01777 -0.00089 0.00006 0.00235 C6 1 0.671774 0.680220 0.169784 11.00000 0.02057 0.01539 = 0.02109 -0.00242 -0.00012 -0.00215 AFIX 43 H6 2 0.702408 0.819034 0.200751 11.00000 -1.20000 AFIX 0 C7 1 0.747432 0.591013 0.086025 11.00000 0.01845 0.01772 = 0.02053 0.00130 0.00172 -0.00196 AFIX 43 H7 2 0.826778 0.671634 0.058525 11.00000 -1.20000 AFIX 0 HKLF 4 REM fa118_s in P2(1)/n REM wR2 = 0.0978, GooF = S = 1.037, Restrained GooF = 1.037 for all data REM R1 = 0.0340 for 1295 Fo > 4sig(Fo) and 0.0440 for all 1571 data REM 120 parameters refined using 0 restraints END WGHT 0.0535 0.2213 REM Instructions for potential hydrogen bonds HTAB N1 O2_$1 HTAB N1 O1_$2 HTAB N1 O1_$3 HTAB N1 O2_$3 HTAB N2 O2_$3 HTAB N2 O1_$4 REM Highest difference peak 0.314, deepest hole -0.209, 1-sigma level 0.045 Q1 1 0.7467 0.3425 -0.0038 11.00000 0.05 0.31 Q2 1 0.5543 0.3220 0.1277 11.00000 0.05 0.26 Q3 1 0.5191 0.6107 0.2540 11.00000 0.05 0.25 Q4 1 0.6189 0.6100 0.2015 11.00000 0.05 0.24 Q5 1 0.5275 0.4813 0.1777 11.00000 0.05 0.24 ; _cod_data_source_file suppl_j_ncrs-2020-0510_suppl.cif _cod_data_source_block g _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 8104918 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _iucr_geom_bonds_special_details ; C~g~(1) is the centroid of carbon atoms C2--C7. ; loop_ _space_group_symop_operation_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_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.85407(10) 0.41707(15) -0.11063(7) 0.0237(2) Uani 1 1 d . . . . . O2 O 0.77074(10) 0.08228(15) -0.07068(8) 0.0261(2) Uani 1 1 d . . . . . N1 N 0.37216(11) 0.25979(18) 0.18943(9) 0.0199(2) Uani 1 1 d . . . . . H711 H 0.3488(18) 0.140(3) 0.1459(14) 0.032(4) Uiso 1 1 d . . . . . H712 H 0.291(2) 0.361(3) 0.1745(14) 0.039(5) Uiso 1 1 d . . . . . H713 H 0.374(2) 0.210(3) 0.2691(16) 0.047(5) Uiso 1 1 d . . . . . N2 N 0.47055(12) 0.66069(19) 0.29016(9) 0.0236(3) Uani 1 1 d . . . . . H721 H 0.4261(19) 0.567(3) 0.3337(14) 0.035(5) Uiso 1 1 d . . . . . H722 H 0.5114(19) 0.781(3) 0.3234(14) 0.035(4) Uiso 1 1 d . . . . . C1 C 0.78346(13) 0.2857(2) -0.05217(10) 0.0189(3) Uani 1 1 d . . . . . C2 C 0.70840(13) 0.38375(19) 0.04149(9) 0.0172(3) Uani 1 1 d . . . . . C3 C 0.58797(12) 0.27305(19) 0.08042(9) 0.0173(3) Uani 1 1 d . . . . . H3 H 0.560296 0.131288 0.051671 0.021 Uiso 1 1 calc R U . . . C4 C 0.50862(12) 0.36681(19) 0.16011(9) 0.0169(3) Uani 1 1 d . . . . . C5 C 0.55061(13) 0.56941(19) 0.20983(10) 0.0173(3) Uani 1 1 d . . . . . C6 C 0.67177(13) 0.6802(2) 0.16978(10) 0.0191(3) Uani 1 1 d . . . . . H6 H 0.702408 0.819034 0.200751 0.023 Uiso 1 1 calc R U . . . C7 C 0.74743(13) 0.5910(2) 0.08603(10) 0.0189(3) Uani 1 1 d . . . . . H7 H 0.826778 0.671634 0.058525 0.023 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0262(5) 0.0226(5) 0.0237(5) -0.0004(4) 0.0097(4) -0.0029(4) O2 0.0314(5) 0.0189(5) 0.0295(5) -0.0050(4) 0.0106(4) -0.0020(4) N1 0.0200(5) 0.0169(5) 0.0238(5) -0.0026(4) 0.0071(4) -0.0036(4) N2 0.0254(5) 0.0213(6) 0.0254(6) -0.0075(5) 0.0080(4) -0.0025(4) C1 0.0179(5) 0.0199(6) 0.0189(5) -0.0002(5) 0.0022(4) 0.0004(4) C2 0.0187(5) 0.0161(6) 0.0171(5) 0.0010(4) 0.0026(4) 0.0006(4) C3 0.0205(6) 0.0126(5) 0.0186(6) -0.0005(4) 0.0016(4) -0.0005(4) C4 0.0165(5) 0.0160(5) 0.0182(6) 0.0015(4) 0.0023(4) -0.0014(4) C5 0.0174(5) 0.0164(6) 0.0178(5) -0.0009(4) 0.0001(4) 0.0024(4) C6 0.0206(6) 0.0154(5) 0.0211(6) -0.0024(4) -0.0001(4) -0.0022(4) C7 0.0184(5) 0.0177(6) 0.0205(6) 0.0013(5) 0.0017(4) -0.0020(4) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C4 N1 H711 111.4(10) . . C4 N1 H712 108.2(10) . . H711 N1 H712 105.8(15) . . C4 N1 H713 115.2(11) . . H711 N1 H713 107.4(15) . . H712 N1 H713 108.5(15) . . C5 N2 H721 117.2(11) . . C5 N2 H722 115.2(11) . . H721 N2 H722 115.8(15) . . O2 C1 O1 123.66(11) . . O2 C1 C2 118.97(11) . . O1 C1 C2 117.35(11) . . C3 C2 C7 118.39(10) . . C3 C2 C1 119.15(10) . . C7 C2 C1 122.29(10) . . C4 C3 C2 120.71(11) . . C4 C3 H3 119.6 . . C2 C3 H3 119.6 . . C3 C4 C5 121.74(10) . . C3 C4 N1 119.41(10) . . C5 C4 N1 118.76(10) . . N2 C5 C4 121.09(11) . . N2 C5 C6 121.76(11) . . C4 C5 C6 117.05(10) . . C7 C6 C5 121.24(11) . . C7 C6 H6 119.4 . . C5 C6 H6 119.4 . . C6 C7 C2 120.73(11) . . C6 C7 H7 119.6 . . C2 C7 H7 119.6 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 C1 1.2734(14) . O2 C1 1.2543(15) . N1 C4 1.4602(14) . N1 H711 0.911(18) . N1 H712 0.958(19) . N1 H713 1.01(2) . N2 C5 1.3798(15) . N2 H721 0.893(18) . N2 H722 0.895(19) . C1 C2 1.4971(16) . C2 C3 1.3926(15) . C2 C7 1.3968(16) . C3 C4 1.3764(15) . C3 H3 0.9500 . C4 C5 1.4018(16) . C5 C6 1.4039(16) . C6 C7 1.3841(16) . C6 H6 0.9500 . C7 H7 0.9500 . loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H711 O2 0.911(18) 1.898(19) 2.7673(14) 158.6(15) 3_655 N1 H712 O1 0.958(19) 1.98(2) 2.9160(15) 166.4(15) 3_665 N1 H713 O1 1.01(2) 1.67(2) 2.6694(14) 167.6(18) 4_566 N2 H721 O2 0.893(18) 2.102(18) 2.9674(15) 163.0(16) 4_566 N2 H722 O1 0.895(19) 2.487(17) 3.0504(14) 121.4(13) 4_576 C6 H6 C~g~(1) 0.95 2.66 3.4370(13) 139 2_655 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 O2 C1 C2 C3 -22.16(17) . . . . O1 C1 C2 C3 156.09(11) . . . . O2 C1 C2 C7 162.80(11) . . . . O1 C1 C2 C7 -18.96(17) . . . . C7 C2 C3 C4 0.60(17) . . . . C1 C2 C3 C4 -174.64(11) . . . . C2 C3 C4 C5 -3.90(18) . . . . C2 C3 C4 N1 172.50(11) . . . . C3 C4 C5 N2 -179.56(11) . . . . N1 C4 C5 N2 4.02(17) . . . . C3 C4 C5 C6 4.01(17) . . . . N1 C4 C5 C6 -172.41(10) . . . . N2 C5 C6 C7 -177.35(11) . . . . C4 C5 C6 C7 -0.94(17) . . . . C5 C6 C7 C2 -2.24(18) . . . . C3 C2 C7 C6 2.42(18) . . . . C1 C2 C7 C6 177.51(11) . . . .