#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/04/2200420.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_2200420 loop_ _publ_author_name 'H\'ector Novoa de Armas' 'Peeters, Oswald M.' 'Blaton, Norbert M.' 'De Ranter, Camiel J.' 'Xu\'arez Marill, Lisbet' _publ_section_title ; 2-(4-Methoxyphenyl)aminobenzoic acid ; _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o638 _journal_page_last o640 _journal_paper_doi 10.1107/S1600536801010364 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C14 H13 N1 O3' _chemical_formula_moiety 'C14 H13 N1 O3' _chemical_formula_sum 'C14 H13 N O3' _chemical_formula_weight 243.25 _space_group_IT_number 7 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P -2yc' _symmetry_space_group_name_H-M 'P 1 c 1' _cell_angle_alpha 90.00000 _cell_angle_beta 107.160(5) _cell_angle_gamma 90.00000 _cell_formula_units_Z 8 _cell_length_a 12.6506(6) _cell_length_b 10.1894(5) _cell_length_c 19.8565(12) _cell_measurement_temperature 293 _cell_volume 2445.6(2) _exptl_crystal_density_diffrn 1.321 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius ; _cod_original_sg_symbol_H-M 'P c' _cod_database_code 2200420 loop_ _symmetry_equiv_pos_as_xyz X,Y,Z X,-Y,1/2+Z 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 O8 .047(3) .057(3) .070(4) -.014(3) .019(3) -.025(3) O9 .057(3) .041(3) .065(3) -.011(3) .029(3) -.019(3) O17 .046(3) .082(4) .076(4) -.008(3) .020(3) .017(3) N10 .045(4) .050(4) .073(4) -.011(3) .023(3) -.019(3) C1 .042(4) .032(4) .041(4) -.007(3) .016(3) .002(3) C2 .049(4) .048(4) .034(3) -.006(4) .015(3) .001(3) C3 .050(4) .037(4) .045(4) -.008(3) .009(3) -.012(3) C4 .066(6) .043(4) .046(4) .005(4) .011(4) -.009(3) C5 .069(6) .048(5) .056(5) .002(4) .032(4) -.012(4) C6 .056(5) .038(4) .063(5) .008(4) .035(4) -.001(3) C7 .038(4) .040(4) .044(4) -.001(4) .008(3) .007(3) C11 .052(5) .036(4) .053(4) -.006(3) .016(4) -.009(3) C12 .053(4) .066(4) .035(3) .003(3) .008(3) -.004(3) C13 .054(4) .073(5) .042(3) .006(4) .017(3) .000(3) C14 .031(4) .051(4) .052(4) .010(3) .011(3) .015(3) C15 .046(4) .043(4) .042(3) .000(3) .001(3) .005(3) C16 .054(4) .040(3) .043(3) -.003(3) .019(3) .002(3) C18 .059(5) .123(7) .100(6) .011(5) .046(5) .047(6) O28 .052(3) .045(3) .060(3) .005(3) .015(3) .014(2) O29 .049(3) .043(3) .053(3) .002(3) .009(3) .011(2) O37 .047(3) .071(4) .090(4) .005(3) .022(3) -.007(3) N30 .053(4) .042(4) .066(4) .006(3) .013(3) .016(3) C21 .060(5) .032(4) .037(3) .002(4) .012(3) -.003(3) C22 .048(4) .029(4) .046(4) .001(3) .004(4) .000(3) C23 .054(5) .043(4) .062(5) .010(4) .012(4) .012(3) C24 .079(7) .054(5) .048(5) .017(5) .017(5) .011(4) C25 .077(7) .050(5) .051(4) -.012(5) .021(5) .008(4) C26 .053(5) .047(4) .045(4) .007(4) .012(3) .000(3) C27 .055(5) .030(4) .039(4) .008(4) .015(3) .003(3) C31 .042(4) .049(4) .045(4) .009(4) .008(3) .015(3) C32 .052(4) .035(4) .088(5) -.005(3) .020(4) -.007(3) C33 .071(5) .040(4) .094(5) .011(4) .030(4) -.005(4) C34 .055(5) .046(5) .060(5) .003(4) .017(4) .010(4) C35 .053(4) .049(4) .058(4) -.012(3) .008(3) .004(3) C36 .058(4) .039(4) .043(3) -.006(3) .010(3) .003(3) C38 .066(5) .092(7) .116(7) .016(5) .047(5) -.009(5) O48 .046(3) .052(3) .061(3) -.014(3) .015(3) -.021(2) O49 .051(3) .044(3) .062(3) -.011(3) .021(3) -.017(3) O57 .050(4) .063(4) .089(4) -.007(3) .021(3) .005(3) N50 .049(4) .047(4) .086(5) -.012(3) .025(4) -.020(4) C41 .038(4) .039(4) .043(4) -.009(3) .015(3) -.004(3) C42 .050(5) .035(4) .048(4) -.006(4) .020(4) -.005(3) C43 .060(5) .050(5) .042(4) -.009(4) .007(4) -.011(3) C44 .072(6) .039(4) .048(4) .002(4) .020(4) -.016(4) C45 .060(6) .048(5) .053(4) -.002(4) .027(4) -.003(4) C46 .050(4) .044(4) .052(4) .000(4) .018(4) -.001(3) C47 .042(4) .037(4) .044(4) -.001(3) .014(3) .001(3) C51 .048(5) .035(4) .057(4) -.005(4) .019(4) -.008(3) C52 .052(4) .047(4) .096(6) .003(4) .025(4) -.002(4) C53 .052(4) .044(4) .086(5) -.003(3) .023(4) -.001(3) C54 .036(4) .048(4) .050(4) .002(3) .012(3) .005(3) C55 .049(4) .046(4) .058(4) .002(3) .009(3) .010(3) C56 .056(4) .037(4) .062(4) -.005(3) .008(3) -.003(3) C58 .067(5) .081(6) .109(7) -.022(5) .024(5) -.003(5) O68 .052(3) .048(3) .055(3) .005(3) .015(3) .010(2) O69 .045(3) .042(3) .058(3) .003(3) .011(3) .011(2) O77 .042(3) .079(4) .081(4) .002(3) .019(3) -.007(3) N70 .052(4) .043(4) .076(4) .012(3) .023(4) .027(3) C61 .053(5) .028(4) .037(3) -.003(3) .013(3) -.002(3) C62 .051(5) .025(4) .051(4) -.002(3) .012(4) .002(3) C63 .051(5) .049(5) .063(5) .003(4) .019(4) .010(4) C64 .063(6) .045(4) .051(4) .012(4) .021(4) .011(4) C65 .059(5) .049(4) .054(4) -.007(4) .021(4) .011(4) C66 .050(4) .044(4) .044(4) .009(4) .012(3) .004(3) C67 .051(5) .032(4) .044(4) .009(4) .014(4) -.004(3) C71 .046(4) .049(4) .040(4) .001(4) .009(3) .012(3) C72 .052(4) .056(4) .051(4) .001(3) .007(3) .008(3) C73 .053(4) .070(4) .047(3) .008(4) .016(3) -.005(3) C74 .055(5) .041(4) .056(5) -.003(4) .011(4) .001(4) C75 .040(3) .053(4) .046(3) -.005(3) .008(3) -.003(3) C76 .054(4) .045(3) .041(3) -.005(3) .010(3) .001(3) C78 .068(5) .109(7) .108(7) -.002(5) .046(5) -.033(6) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_type_symbol O8 -.1675(5) -.2522(6) .9062(3) .0576(19) Uani 1.000 O O9 .0010(5) -.2921(5) .8998(3) .0520(17) Uani 1.000 O O17 .5920(5) .0251(6) .9857(3) .068(2) Uani 1.000 O N10 .1637(5) -.1329(6) .9690(4) .055(2) Uani 1.000 N C1 -.0252(6) -.1262(6) .9783(3) .038(2) Uani 1.000 C C2 .0869(7) -.0779(7) .9988(4) .043(2) Uani 1.000 C C3 .1133(7) .0269(7) 1.0487(4) .045(2) Uani 1.000 C C4 .0360(7) .0802(7) 1.0740(4) .053(3) Uani 1.000 C C5 -.0707(8) .0335(8) 1.0555(4) .055(3) Uani 1.000 C C6 -.1007(7) -.0680(7) 1.0090(4) .049(3) Uani 1.000 C C7 -.0599(7) -.2298(7) .9260(4) .042(2) Uani 1.000 C C11 .2732(7) -.0905(7) .9774(4) .047(3) Uani 1.000 C C12 .3026(6) -.0812(6) .9131(3) .052(2) Uani 1.000 C C13 .4084(6) -.0458(7) .9151(3) .056(2) Uani 1.000 C C14 .4839(6) -.0146(7) .9789(4) .045(2) Uani 1.000 C C15 .4543(5) -.0226(6) 1.0394(3) .046(2) Uani 1.000 C C16 .3493(6) -.0596(6) 1.0380(3) .0447(19) Uani 1.000 C C18 .6217(7) .0472(9) .9230(5) .089(3) Uani 1.000 C O28 .9406(5) .0036(5) 1.3105(3) .0527(17) Uani 1.000 O O29 .7693(4) -.0515(5) 1.3102(3) .0496(17) Uani 1.000 O O37 .1828(5) .2495(6) 1.2364(4) .069(2) Uani 1.000 O N30 .6029(6) .0958(6) 1.2331(3) .055(2) Uani 1.000 N C21 .7921(7) .1228(7) 1.2360(4) .043(2) Uani 1.000 C C22 .6814(7) .1610(7) 1.2109(4) .043(2) Uani 1.000 C C23 .6510(7) .2591(7) 1.1603(5) .054(3) Uani 1.000 C C24 .7303(8) .3202(8) 1.1355(4) .061(3) Uani 1.000 C C25 .8408(8) .2856(8) 1.1617(5) .059(3) Uani 1.000 C C26 .8696(7) .1887(7) 1.2117(4) .049(3) Uani 1.000 C C27 .8321(7) .0188(7) 1.2881(4) .041(3) Uani 1.000 C C31 .4971(6) .1431(7) 1.2336(4) .046(2) Uani 1.000 C C32 .4750(6) .2707(6) 1.2418(4) .058(3) Uani 1.000 C C33 .3698(7) .3120(7) 1.2419(4) .067(3) Uani 1.000 C C34 .2861(8) .2213(8) 1.2347(5) .054(3) Uani 1.000 C C35 .3080(6) .0912(6) 1.2248(3) .055(2) Uani 1.000 C C36 .4113(6) .0500(6) 1.2235(3) .048(2) Uani 1.000 C C38 .1600(7) .3800(8) 1.2525(5) .087(4) Uani 1.000 C O48 -.1754(4) .2507(5) .8959(3) .0532(17) Uani 1.000 O O49 -.0049(5) .1977(5) .8979(3) .0514(17) Uani 1.000 O O57 .5815(5) .5101(6) .9763(4) .067(2) Uani 1.000 O N50 .1610(6) .3467(6) .9746(4) .060(3) Uani 1.000 N C41 -.0328(6) .3711(7) .9723(4) .039(2) Uani 1.000 C C42 .0818(7) .4063(7) .9983(4) .043(3) Uani 1.000 C C43 .1081(8) .5060(7) 1.0510(4) .052(3) Uani 1.000 C C44 .0311(8) .5673(7) 1.0735(4) .053(3) Uani 1.000 C C45 -.0803(8) .5336(8) 1.0477(4) .051(3) Uani 1.000 C C46 -.1111(7) .4350(7) .9986(4) .048(2) Uani 1.000 C C47 -.0670(7) .2662(7) .9204(4) .041(2) Uani 1.000 C C51 .2681(7) .3956(7) .9819(4) .046(3) Uani 1.000 C C52 .2865(6) .5259(7) .9671(4) .064(3) Uani 1.000 C C53 .3909(6) .5692(6) .9660(4) .060(3) Uani 1.000 C C54 .4753(6) .4786(7) .9787(4) .045(2) Uani 1.000 C C55 .4579(6) .3503(6) .9899(3) .052(2) Uani 1.000 C C56 .3541(6) .3096(6) .9917(4) .054(2) Uani 1.000 C C58 .6019(7) .6403(7) .9594(5) .086(3) Uani 1.000 C O68 .9411(5) .4901(5) 1.3087(3) .0518(17) Uani 1.000 O O69 .7720(4) .4446(5) 1.3161(3) .0492(17) Uani 1.000 O O77 .1817(5) .7652(6) 1.2270(4) .067(2) Uani 1.000 O N70 .6069(6) .5983(6) 1.2426(4) .056(2) Uani 1.000 N C61 .7927(7) .6130(6) 1.2369(4) .039(2) Uani 1.000 C C62 .6837(7) .6572(6) 1.2162(4) .043(3) Uani 1.000 C C63 .6551(7) .7581(8) 1.1689(5) .054(3) Uani 1.000 C C64 .7332(7) .8154(7) 1.1407(4) .052(3) Uani 1.000 C C65 .8424(8) .7721(8) 1.1622(5) .053(3) Uani 1.000 C C66 .8689(7) .6719(7) 1.2095(4) .046(2) Uani 1.000 C C67 .8330(7) .5093(7) 1.2906(4) .042(3) Uani 1.000 C C71 .5011(6) .6442(7) 1.2412(4) .046(2) Uani 1.000 C C72 .4702(6) .6587(6) 1.2992(3) .055(2) Uani 1.000 C C73 .3650(6) .6975(7) 1.2988(3) .056(2) Uani 1.000 C C74 .2857(7) .7243(7) 1.2353(5) .052(3) Uani 1.000 C C75 .3138(6) .7069(6) 1.1725(3) .0473(19) Uani 1.000 C C76 .4190(6) .6645(6) 1.1742(3) .0475(19) Uani 1.000 C C78 .1523(7) .7907(9) 1.2898(5) .091(4) Uani 1.000 C H3 .1853 .0588 1.0638 .057 Uiso 1.000 H H4 .0550 .1507 1.1049 .066 Uiso 1.000 H H5 -.1224 .0712 1.0746 .068 Uiso 1.000 H H6 -.1728 -.0996 .9974 .061 Uiso 1.000 H H8 -.1823 -.3097 .8760 .072 Uiso 1.000 H H10 .1418 -.2002 .9425 .069 Uiso 1.000 H H12 .2502 -.0990 .8702 .066 Uiso 1.000 H H13 .4289 -.0429 .8738 .070 Uiso 1.000 H H15 .5059 -.0027 1.0823 .058 Uiso 1.000 H H16 .3307 -.0631 1.0799 .056 Uiso 1.000 H H18A .6285 -.0355 .9015 .111 Uiso 1.000 H H18B .6911 .0930 .9343 .111 Uiso 1.000 H H18C .5656 .0990 .8910 .111 Uiso 1.000 H H23 .5772 .2840 1.1430 .068 Uiso 1.000 H H24 .7091 .3848 1.1010 .076 Uiso 1.000 H H25 .8943 .3273 1.1457 .073 Uiso 1.000 H H26 .9439 .1664 1.2300 .061 Uiso 1.000 H H28 .9560 -.0585 1.3380 .066 Uiso 1.000 H H30 .6194 .0172 1.2485 .068 Uiso 1.000 H H32 .5311 .3325 1.2475 .073 Uiso 1.000 H H33 .3561 .4006 1.2469 .084 Uiso 1.000 H H35 .2517 .0297 1.2188 .069 Uiso 1.000 H H36 .4242 -.0380 1.2162 .060 Uiso 1.000 H H38A .2033 .4009 1.2997 .108 Uiso 1.000 H H38B .0828 .3881 1.2486 .108 Uiso 1.000 H H38C .1784 .4393 1.2201 .108 Uiso 1.000 H H43 .1819 .5296 1.0706 .065 Uiso 1.000 H H44 .0524 .6335 1.1070 .066 Uiso 1.000 H H45 -.1331 .5773 1.0634 .065 Uiso 1.000 H H46 -.1850 .4101 .9824 .059 Uiso 1.000 H H48 -.1893 .1896 .8679 .067 Uiso 1.000 H H50 .1439 .2727 .9533 .075 Uiso 1.000 H H52 .2281 .5852 .9576 .081 Uiso 1.000 H H53 .4030 .6567 .9571 .075 Uiso 1.000 H H55 .5152 .2899 .9962 .066 Uiso 1.000 H H56 .3428 .2216 .9999 .067 Uiso 1.000 H H58A .5483 .6654 .9161 .108 Uiso 1.000 H H58B .6748 .6461 .9541 .108 Uiso 1.000 H H58C .5966 .6978 .9966 .108 Uiso 1.000 H H63 .5827 .7890 1.1552 .067 Uiso 1.000 H H64 .7122 .8824 1.1076 .065 Uiso 1.000 H H65 .8957 .8104 1.1448 .067 Uiso 1.000 H H66 .9415 .6419 1.2239 .058 Uiso 1.000 H H68 .9574 .4272 1.3355 .065 Uiso 1.000 H H70 .6257 .5235 1.2627 .070 Uiso 1.000 H H72 .5221 .6420 1.3425 .068 Uiso 1.000 H H73 .3476 .7055 1.3409 .070 Uiso 1.000 H H75 .2616 .7238 1.1294 .059 Uiso 1.000 H H76 .4362 .6493 1.1325 .059 Uiso 1.000 H H78A .1526 .7099 1.3148 .113 Uiso 1.000 H H78B .0797 .8288 1.2778 .113 Uiso 1.000 H H78C .2047 .8504 1.3192 .113 Uiso 1.000 H loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O8 C7 . . 1.321(11) yes O9 C7 . . 1.226(10) yes O17 C14 . . 1.394(10) yes O17 C18 . . 1.421(11) yes O8 H8 . . .820 no O28 C27 . . 1.321(11) yes O29 C27 . . 1.242(10) yes O37 C34 . . 1.348(12) yes O37 C38 . . 1.417(10) yes O28 H28 . . .820 no O48 C47 . . 1.322(10) yes O49 C47 . . 1.229(10) yes O57 C58 . . 1.411(10) yes O57 C54 . . 1.396(10) yes O48 H48 . . .820 no O68 C67 . . 1.322(11) yes O69 C67 . . 1.232(10) yes O77 C74 . . 1.343(11) yes O77 C78 . . 1.426(12) yes O68 H68 . . .820 no N10 C2 . . 1.395(11) yes N10 C11 . . 1.413(11) yes N10 H10 . . .860 no N30 C31 . . 1.425(11) yes N30 C22 . . 1.371(11) yes N30 H30 . . .860 no N50 C42 . . 1.368(11) yes N50 C51 . . 1.410(12) yes N50 H50 . . .860 no N70 C62 . . 1.371(11) yes N70 C71 . . 1.410(11) yes N70 H70 . . .860 no C1 C7 . . 1.455(9) no C1 C6 . . 1.407(11) no C1 C2 . . 1.442(12) no C2 C3 . . 1.428(10) no C3 C4 . . 1.339(12) no C4 C5 . . 1.375(13) no C5 C6 . . 1.364(11) no C11 C12 . . 1.434(10) no C11 C16 . . 1.338(10) no C12 C13 . . 1.375(11) no C13 C14 . . 1.380(10) no C14 C15 . . 1.362(10) no C15 C16 . . 1.373(10) no C3 H3 . . .930 no C4 H4 . . .930 no C5 H5 . . .930 no C6 H6 . . .930 no C12 H12 . . .930 no C13 H13 . . .930 no C15 H15 . . .930 no C16 H16 . . .930 no C18 H18B . . .960 no C18 H18A . . .960 no C18 H18C . . .960 no C21 C22 . . 1.396(12) no C21 C27 . . 1.463(10) no C21 C26 . . 1.387(12) no C22 C23 . . 1.389(11) no C23 C24 . . 1.389(13) no C24 C25 . . 1.386(14) no C25 C26 . . 1.371(11) no C31 C32 . . 1.350(10) no C31 C36 . . 1.411(10) no C32 C33 . . 1.396(12) no C33 C34 . . 1.381(13) no C34 C35 . . 1.380(10) no C35 C36 . . 1.380(11) no C23 H23 . . .930 no C24 H24 . . .930 no C25 H25 . . .930 no C26 H26 . . .930 no C32 H32 . . .930 no C33 H33 . . .930 no C35 H35 . . .930 no C36 H36 . . .930 no C38 H38B . . .960 no C38 H38A . . .960 no C38 H38C . . .960 no C41 C47 . . 1.459(10) no C41 C42 . . 1.434(12) no C41 C46 . . 1.408(12) no C42 C43 . . 1.426(10) no C43 C44 . . 1.340(13) no C44 C45 . . 1.393(14) no C45 C46 . . 1.374(11) no C51 C52 . . 1.394(10) no C51 C56 . . 1.365(11) no C52 C53 . . 1.399(11) no C53 C54 . . 1.377(10) no C54 C55 . . 1.355(9) no C55 C56 . . 1.388(11) no C43 H43 . . .930 no C44 H44 . . .930 no C45 H45 . . .930 no C46 H46 . . .930 no C52 H52 . . .930 no C53 H53 . . .930 no C55 H55 . . .930 no C56 H56 . . .930 no C58 H58A . . .960 no C58 H58C . . .960 no C58 H58B . . .960 no C61 C66 . . 1.377(12) no C61 C67 . . 1.481(10) no C61 C62 . . 1.392(12) no C62 C63 . . 1.367(11) no C63 C64 . . 1.399(13) no C64 C65 . . 1.392(14) no C65 C66 . . 1.361(11) no C71 C76 . . 1.441(10) no C71 C72 . . 1.329(10) no C72 C73 . . 1.386(11) no C73 C74 . . 1.387(11) no C74 C75 . . 1.405(11) no C75 C76 . . 1.390(11) no C63 H63 . . .930 no C64 H64 . . .930 no C65 H65 . . .930 no C66 H66 . . .930 no C72 H72 . . .930 no C73 H73 . . .930 no C75 H75 . . .930 no C76 H76 . . .930 no C78 H78A . . .960 no C78 H78B . . .960 no C78 H78C . . .960 no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 175719 2 PubChem 139064882