#------------------------------------------------------------------------------ #$Date: 2008-01-13 23:15:36 +0100 (Sun, 13 Jan 2008) $ #$Revision: 14 $ #$URL: svn://www.crystallography.net/cod/cif/2/2011558.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_2011558 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2000 _journal_volume 56 _journal_page_first e535 _journal_page_last e535 _publ_section_title ; 4-Anilino-3-nitropyridine ; loop_ _publ_author_name 'Lynch, Daniel E.' 'McClenaghan, Ian' _chemical_formula_sum 'C11 H9 N3 O2' _chemical_formula_weight 215.21 _chemical_melting_point '387 - 388 K' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.9036(2) _cell_length_b 19.9452(4) _cell_length_c 13.6660(3) _cell_angle_alpha 90.00 _cell_angle_beta 133.5610(10) _cell_angle_gamma 90.00 _cell_volume 1956.12(7) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _exptl_crystal_density_diffrn 1.462 _diffrn_ambient_temperature 150(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 N1A -.27770(15) .26138(5) -.11988(14) .0318(3) Uani d . 1 . . N C2A -.13396(18) .30229(7) -.05795(15) .0287(3) Uani d . 1 . . C H2A -.1581 .3491 -.0713 .036 Uiso calc R 1 . . H C3A .05052(18) .28132(6) .02560(15) .0246(3) Uani d . 1 . . C N31A .18796(15) .33360(5) .08462(13) .0280(3) Uani d . 1 . . N O31A .13772(15) .39193(5) .05191(13) .0491(3) Uani d . 1 . . O O32A .35416(13) .31784(5) .16729(12) .0377(3) Uani d . 1 . . O C4A .09858(18) .21252(6) .05103(14) .0241(3) Uani d . 1 . . C C5A -.05793(18) .16999(6) -.01723(16) .0276(3) Uani d . 1 . . C H5A -.0406 .1228 -.0081 .034 Uiso calc R 1 . . H C6A -.23285(19) .19553(6) -.09567(16) .0300(3) Uani d . 1 . . C H6A -.3320 .1645 -.1370 .037 Uiso calc R 1 . . H N41A .27452(16) .18850(5) .13343(13) .0271(3) Uani d . 1 . . N H41A .368(3) .2173(9) .183(2) .048(5) Uiso d . 1 . . H C7A .32538(18) .11938(6) .15920(15) .0250(3) Uani d . 1 . . C C8A .46514(17) .09882(6) .29228(15) .0277(3) Uani d . 1 . . C H8A .5221 .1304 .3633 .035 Uiso calc R 1 . . H C9A .52205(19) .03260(6) .32202(16) .0318(3) Uani d . 1 . . C H9A .6183 .0188 .4134 .040 Uiso calc R 1 . . H C10A .4393(2) -.01360(7) .21916(17) .0338(4) Uani d . 1 . . C H10A .4770 -.0592 .2397 .042 Uiso calc R 1 . . H C11A .3014(2) .00683(6) .08639(17) .0336(3) Uani d . 1 . . C H11A .2452 -.0249 .0157 .042 Uiso calc R 1 . . H C12A .24441(18) .07330(6) .05522(16) .0296(3) Uani d . 1 . . C H12A .1509 .0872 -.0363 .037 Uiso calc R 1 . . H N1B .74445(15) .75523(5) .62062(14) .0314(3) Uani d . 1 . . N C2B .60329(19) .79626(6) .53326(16) .0279(3) Uani d . 1 . . C H2B .6308 .8423 .5364 .035 Uiso calc R 1 . . H C3B .41683(18) .77663(6) .43677(15) .0248(3) Uani d . 1 . . C N31B .28238(15) .82911(5) .35577(13) .0284(3) Uani d . 1 . . N O31B .33667(14) .88592(5) .36233(13) .0423(3) Uani d . 1 . . O O32B .11555(13) .81565(4) .28263(12) .0386(3) Uani d . 1 . . O C4B .36574(18) .70840(6) .42211(14) .0246(3) Uani d . 1 . . C C5B .51869(19) .66589(6) .51846(16) .0283(3) Uani d . 1 . . C H5B .4978 .6194 .5187 .035 Uiso calc R 1 . . H C6B .69577(19) .69048(7) .61104(16) .0307(3) Uani d . 1 . . C H6B .7929 .6597 .6739 .038 Uiso calc R 1 . . H N41B .18844(16) .68528(5) .32711(13) .0262(3) Uani d . 1 . . N H41B .101(2) .7142(8) .2864(19) .036(4) Uiso d . 1 . . H C7B .13384(18) .61698(6) .29260(15) .0250(3) Uani d . 1 . . C C8B -.02872(17) .59715(6) .25887(15) .0264(3) Uani d . 1 . . C H8B -.0960 .6284 .2640 .033 Uiso calc R 1 . . H C9B -.09257(18) .53186(6) .21786(16) .0305(3) Uani d . 1 . . C H9B -.2033 .5185 .1952 .038 Uiso calc R 1 . . H C10B .00433(19) .48623(7) .20977(16) .0325(3) Uani d . 1 . . C H10B -.0391 .4414 .1821 .041 Uiso calc R 1 . . H C11B .1648(2) .50607(6) .24207(16) .0334(3) Uani d . 1 . . C H11B .2310 .4747 .2361 .042 Uiso calc R 1 . . H C12B .23022(19) .57110(6) .28309(16) .0296(3) Uani d . 1 . . C H12B .3403 .5843 .3046 .037 Uiso calc R 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 N1A .0251(6) .0324(6) .0336(8) .0019(4) .0185(6) .0034(5) C2A .0275(7) .0268(7) .0299(9) .0041(5) .0190(7) .0030(5) C3A .0247(7) .0256(7) .0228(8) -.0005(5) .0161(6) -.0012(5) N31A .0266(6) .0255(6) .0263(7) .0010(4) .0161(6) -.0008(5) O31A .0353(6) .0238(5) .0565(9) .0018(4) .0196(6) .0012(5) O32A .0219(5) .0314(5) .0411(7) -.0005(4) .0146(5) -.0008(4) C4A .0236(6) .0275(7) .0217(8) .0027(5) .0158(6) .0010(5) C5A .0255(7) .0269(7) .0299(9) .0007(5) .0189(7) .0018(6) C6A .0236(7) .0313(7) .0308(9) -.0008(5) .0172(7) .0019(6) N41A .0211(6) .0246(6) .0288(7) .0005(4) .0146(6) -.0013(5) C7A .0213(6) .0244(6) .0300(9) .0005(5) .0180(6) .0009(5) C8A .0237(7) .0317(7) .0272(9) -.0015(5) .0173(7) -.0019(6) C9A .0255(7) .0333(7) .0328(9) .0034(5) .0187(7) .0075(6) C10A .0298(7) .0246(7) .0449(11) .0020(5) .0249(8) .0035(6) C11A .0318(7) .0274(7) .0400(10) -.0033(5) .0242(7) -.0064(6) C12A .0254(7) .0316(7) .0272(9) .0008(5) .0164(7) -.0005(6) N1B .0243(6) .0310(6) .0319(8) -.0008(4) .0167(6) -.0049(5) C2B .0252(7) .0276(7) .0312(9) -.0025(5) .0195(7) -.0044(6) C3B .0236(7) .0264(7) .0245(8) .0009(5) .0165(6) -.0009(5) N31B .0249(6) .0267(6) .0312(8) -.0010(4) .0184(6) -.0015(5) O31B .0335(6) .0262(5) .0546(9) -.0022(4) .0255(6) .0024(5) O32B .0214(5) .0325(5) .0470(8) -.0003(4) .0178(5) .0015(5) C4B .0234(6) .0288(7) .0240(8) -.0022(5) .0172(6) -.0024(5) C5B .0274(7) .0260(7) .0285(9) .0001(5) .0181(7) .0002(5) C6B .0257(7) .0320(7) .0282(9) .0024(5) .0162(7) -.0007(6) N41B .0208(6) .0243(6) .0285(7) -.0011(4) .0151(5) -.0009(5) C7B .0226(6) .0258(6) .0212(8) -.0018(5) .0130(6) .0003(5) C8B .0216(6) .0305(7) .0225(8) .0015(5) .0134(6) .0021(5) C9B .0238(7) .0315(7) .0301(9) -.0044(5) .0162(7) .0000(6) C10B .0293(7) .0263(7) .0344(10) -.0037(5) .0190(7) -.0028(6) C11B .0315(8) .0303(7) .0379(10) -.0007(5) .0238(8) -.0043(6) C12B .0258(7) .0323(7) .0312(9) -.0030(5) .0198(7) -.0031(6) 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 N1A C2A . 1.3222(17) ? N1A C6A . 1.3524(16) ? C2A C3A . 1.3933(18) ? C2A H2A . .9500 ? C3A C4A . 1.4150(17) ? C3A N31A . 1.4413(16) ? N31A O31A . 1.2224(14) ? N31A O32A . 1.2335(14) ? C4A N41A . 1.3526(16) ? C4A C5A . 1.4141(18) ? C5A C6A . 1.3602(19) ? C5A H5A . .9500 ? C6A H6A . .9500 ? N41A C7A . 1.4260(16) ? N41A H41A . .882(19) ? C7A C8A . 1.386(2) ? C7A C12A . 1.392(2) ? C8A C9A . 1.3825(18) ? C8A H8A . .9500 ? C9A C10A . 1.382(2) ? C9A H9A . .9500 ? C10A C11A . 1.381(2) ? C10A H10A . .9500 ? C11A C12A . 1.3880(18) ? C11A H11A . .9500 ? C12A H12A . .9500 ? N1B C2B . 1.3225(18) ? N1B C6B . 1.3529(16) ? C2B C3B . 1.3950(18) ? C2B H2B . .9500 ? C3B C4B . 1.4173(18) ? C3B N31B . 1.4361(17) ? N31B O31B . 1.2307(13) ? N31B O32B . 1.2349(14) ? C4B N41B . 1.3563(17) ? C4B C5B . 1.4136(19) ? C5B C6B . 1.3634(19) ? C5B H5B . .9500 ? C6B H6B . .9500 ? N41B C7B . 1.4209(16) ? N41B H41B . .851(17) ? C7B C12B . 1.3915(18) ? C7B C8B . 1.3922(18) ? C8B C9B . 1.3860(18) ? C8B H8B . .9500 ? C9B C10B . 1.3812(19) ? C9B H9B . .9500 ? C10B C11B . 1.3818(19) ? C10B H10B . .9500 ? C11B C12B . 1.3841(18) ? C11B H11B . .9500 ? C12B H12B . .9500 ?