#------------------------------------------------------------------------------ #$Date: 2011-09-28 17:24:46 +0300 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/21/2012149.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_2012149 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 961 _journal_page_last 964 _publ_section_title ; Differently coloured polymorphs of 4-[(2-nitrophenyl)azo]phenol ; _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _[local]_cod_cif_authors_sg_H-M 'P 21/n' loop_ _publ_author_name 'Yatsenko, Alexandr V.' 'Paseshnichenko, Ksenia A.' _chemical_formula_moiety 'C12 H9 N3 O3' _chemical_formula_sum 'C12 H9 N3 O3' _chemical_formula_weight 243.22 _symmetry_cell_setting 'monoclinic' 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' _cell_length_a 3.8230(10) _cell_length_b 23.014(8) _cell_length_c 25.437(9) _cell_angle_alpha 90 _cell_angle_beta 92.73(3) _cell_angle_gamma 90 _cell_volume 2235.5(13) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.445 _diffrn_ambient_temperature 293(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 O1 1.1222(10) -.09985(15) .34897(14) .0613(11) Uani d . 1 . . O O21 .6705(11) .34469(16) .24393(15) .0680(12) Uani d . 1 . . O O2 .3855(12) .13177(18) .53379(15) .0966(14) Uani d . 1 . . O O22 1.4789(11) .12091(17) .06884(14) .1001(14) Uani d . 1 . . O O3 .7184(12) .19259(19) .57452(14) .1106(16) Uani d . 1 . . O O23 1.1828(12) .05988(17) .02288(13) .1121(16) Uani d . 1 . . O N1 .6712(9) .12359(14) .38991(14) .0470(10) Uani d . 1 . . N N21 1.1606(9) .12226(15) .20954(13) .0470(10) Uani d . 1 . . N N2 .6877(9) .14127(14) .43656(14) .0463(10) Uani d . 1 . . N N22 1.1487(9) .10482(14) .16238(13) .0462(10) Uani d . 1 . . N N3 .5367(13) .1782(2) .53684(18) .0685(14) Uani d . 1 . . N N23 1.3434(13) .07355(18) .06278(16) .0666(13) Uani d . 1 . . N C1 1.0228(12) -.0444(2) .36164(18) .0483(13) Uani d . 1 . . C C21 .7855(12) .28936(19) .23324(19) .0451(12) Uani d . 1 . . C C2 1.0744(13) -.0219(2) .41173(19) .0496(13) Uani d . 1 . . C C22 .7464(13) .2652(2) .18338(18) .0527(14) Uani d . 1 . . C C3 .9648(12) .0335(2) .42221(17) .0477(13) Uani d . 1 . . C C23 .8646(13) .2107(2) .17472(19) .0512(13) Uani d . 1 . . C C4 .8006(11) .06676(19) .38299(16) .0440(12) Uani d . 1 . . C C24 1.0205(11) .17883(17) .21531(16) .0403(11) Uani d . 1 . . C C5 .7531(13) .04426(19) .33286(18) .0471(12) Uani d . 1 . . C C25 1.0572(13) .2024(2) .26531(17) .0481(13) Uani d . 1 . . C C6 .8604(13) -.01182(19) .32249(18) .0490(13) Uani d . 1 . . C C26 .9412(14) .2579(2) .27327(19) .0526(14) Uani d . 1 . . C C11 .5622(11) .19913(18) .44222(17) .0413(11) Uani d . 1 . . C C31 1.2864(11) .04798(18) .15629(16) .0411(12) Uani d . 1 . . C C12 .4996(13) .2188(2) .49205(18) .0488(12) Uani d . 1 . . C C32 1.3711(12) .03183(19) .10622(18) .0452(12) Uani d . 1 . . C C13 .4036(14) .2753(2) .5024(2) .0623(16) Uani d . 1 . . C C33 1.4829(14) -.0229(2) .0940(2) .0601(15) Uani d . 1 . . C C14 .3603(15) .3129(2) .4610(2) .0664(17) Uani d . 1 . . C C34 1.5147(15) -.0631(2) .1336(2) .0667(16) Uani d . 1 . . C C15 .4207(13) .2947(2) .4110(2) .0574(15) Uani d . 1 . . C C35 1.4299(15) -.0495(2) .1837(2) .0637(16) Uani d . 1 . . C C16 .5177(13) .2379(2) .40111(19) .0504(13) Uani d . 1 . . C C36 1.3137(13) .0064(2) .1953(2) .0523(14) Uani d . 1 . . C H1 1.225(14) -.115(2) .3728(18) .10(2) Uiso d . 1 . . H H2 1.195(9) -.0455(14) .4385(12) .037(11) Uiso d . 1 . . H H3 .994(9) .0495(15) .4582(13) .047(12) Uiso d . 1 . . H H5 .624(10) .0676(15) .3052(13) .046(12) Uiso d . 1 . . H H6 .840(9) -.0306(14) .2876(12) .036(11) Uiso d . 1 . . H H13 .349(11) .2875(17) .5386(15) .067(15) Uiso d . 1 . . H H14 .315(10) .3522(15) .4696(13) .047(13) Uiso d . 1 . . H H15 .394(10) .3245(16) .3820(14) .054(13) Uiso d . 1 . . H H16 .586(9) .2260(15) .3670(13) .036(11) Uiso d . 1 . . H H21 .566(11) .3543(18) .2179(14) .047(17) Uiso d . 1 . . H H22 .646(9) .2901(13) .1545(11) .027(10) Uiso d . 1 . . H H23 .846(9) .1899(15) .1415(13) .040(12) Uiso d . 1 . . H H25 1.146(10) .1783(15) .2939(13) .050(13) Uiso d . 1 . . H H26 .951(10) .2741(15) .3076(14) .054(13) Uiso d . 1 . . H H33 1.561(11) -.0299(18) .0593(15) .073(17) Uiso d . 1 . . H H34 1.585(11) -.1020(17) .1262(15) .064(14) Uiso d . 1 . . H H35 1.433(11) -.0768(16) .2123(14) .057(14) Uiso d . 1 . . H H36 1.253(11) .0155(18) .2285(15) .065(16) 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 O1 .082(3) .039(2) .063(3) .0090(19) .003(2) -.0044(18) O21 .090(3) .046(2) .067(3) .001(2) -.004(3) -.012(2) O2 .117(4) .087(3) .086(3) .001(3) -.001(3) .024(3) O22 .137(4) .085(3) .078(3) -.035(3) -.001(3) .024(2) O3 .134(4) .136(4) .058(2) .027(3) -.031(3) .000(3) O23 .180(5) .104(3) .049(2) .012(3) -.027(3) -.012(2) N1 .049(3) .041(2) .051(2) .000(2) .004(2) -.0025(19) N21 .051(3) .048(2) .042(2) -.001(2) .002(2) .0012(19) N2 .047(3) .047(2) .045(2) .001(2) .002(2) -.0055(19) N22 .052(3) .045(2) .041(2) .003(2) -.001(2) -.0033(19) N3 .074(4) .078(4) .054(3) .024(3) .013(3) .000(3) N23 .097(4) .056(3) .047(3) .003(3) .011(3) -.007(3) C1 .047(3) .044(3) .055(3) -.006(3) .014(3) -.009(3) C21 .042(3) .036(3) .058(3) -.007(2) .006(3) -.003(2) C2 .048(3) .046(3) .054(3) .009(3) -.002(3) .005(3) C22 .066(4) .045(3) .045(3) .002(3) -.009(3) .006(3) C3 .052(3) .053(3) .039(3) -.001(3) .000(3) -.008(3) C23 .063(4) .047(3) .044(3) .005(3) .005(3) -.001(3) C4 .043(3) .042(3) .048(3) .002(2) .012(3) .000(2) C24 .043(3) .038(3) .040(3) -.005(2) .007(2) -.002(2) C5 .052(3) .043(3) .047(3) -.001(3) .002(3) .001(2) C25 .057(3) .047(3) .040(3) -.005(3) .000(3) .004(2) C6 .060(4) .047(3) .040(3) -.005(3) .004(3) -.009(2) C26 .066(4) .051(3) .041(3) -.003(3) .002(3) -.002(3) C11 .037(3) .040(3) .047(3) .000(2) -.001(2) -.006(2) C31 .038(3) .043(3) .043(3) -.004(2) .003(2) -.005(2) C12 .047(3) .058(3) .041(3) .008(3) -.007(2) .000(3) C32 .048(3) .039(3) .049(3) .003(3) .003(2) .001(2) C13 .068(4) .065(4) .054(4) .013(3) .005(3) -.019(3) C33 .052(4) .063(4) .066(4) -.004(3) .010(3) -.009(3) C14 .082(4) .044(3) .073(4) .005(3) -.003(4) -.014(3) C34 .065(4) .044(3) .091(5) .005(3) .000(4) -.018(3) C15 .064(4) .041(3) .066(4) .000(3) -.005(3) .007(3) C35 .064(4) .044(3) .082(4) .001(3) -.005(4) .012(3) C16 .054(3) .048(3) .049(3) -.001(3) .000(3) .002(3) C36 .052(4) .056(3) .048(3) -.004(3) .002(3) .003(3) 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 C1 . 1.373(5) no O1 H1 . .79(5) no O21 C21 . 1.378(5) no O21 H21 . .79(4) no O2 N3 . 1.216(5) no O22 N23 . 1.213(5) no O3 N3 . 1.203(5) no O23 N23 . 1.203(5) no N1 N2 . 1.253(4) no N1 C4 . 1.412(5) no N21 N22 . 1.264(4) no N21 C24 . 1.418(5) no N2 C11 . 1.425(5) no N22 C31 . 1.421(5) no N3 C12 . 1.474(6) no N23 C32 . 1.464(5) no C1 C6 . 1.372(6) no C1 C2 . 1.381(6) no C21 C26 . 1.363(6) no C21 C22 . 1.386(6) no C2 C3 . 1.373(6) no C2 H2 . .97(3) no C22 C23 . 1.354(6) no C22 H22 . .99(3) no C3 C4 . 1.383(5) no C3 H3 . .99(3) no C23 C24 . 1.379(5) no C23 H23 . .97(3) no C4 C5 . 1.380(5) no C24 C25 . 1.383(5) no C5 C6 . 1.384(6) no C5 H5 . 1.00(3) no C25 C26 . 1.372(6) no C25 H25 . .96(3) no C6 H6 . .99(3) no C26 H26 . .95(3) no C11 C12 . 1.377(5) no C11 C16 . 1.379(5) no C31 C36 . 1.379(5) no C31 C32 . 1.380(5) no C12 C13 . 1.380(6) no C32 C33 . 1.370(6) no C13 C14 . 1.365(6) no C13 H13 . .99(4) no C33 C34 . 1.367(7) no C33 H33 . .96(4) no C14 C15 . 1.370(6) no C14 H14 . .95(3) no C34 C35 . 1.368(7) no C34 H34 . .96(4) no C15 C16 . 1.384(6) no C15 H15 . 1.01(3) no C35 C36 . 1.398(6) no C35 H35 . .96(4) no C16 H16 . .96(3) no C36 H36 . .91(4) no _cod_database_code 2012149