#------------------------------------------------------------------------------ #$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $ #$Revision: 14 $ #$URL: svn://www.crystallography.net/cod/cif/2/2009032.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_2009032 _journal_name_full 'Acta Crystallographica' _journal_year 1999 _journal_volume C55 _journal_page_first 1670 _journal_page_last 1672 _publ_section_title ; 5-Amino-4-(4-methoxyphenyl)-2-phenyl-7-(pyrrolidin-1-yl)-1,6-naphthyridine- 8-carbonitrile ; loop_ _publ_author_name 'R.Sankaranarayanan' 'S.Shanmuga Sundara Raj' 'D.Velmurugan' 'Hoong-Kun Fun' 'V.Raghukumar' 'V.T.Ramakrishnan' _chemical_formula_sum 'C26 H23 N5 O' _chemical_formula_weight 421.49 _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.68080(10) _cell_length_b 11.4468(2) _cell_length_c 19.85570(10) _cell_angle_alpha 100.0470(10) _cell_angle_beta 95.8040(10) _cell_angle_gamma 90.3180(10) _cell_volume 2154.84(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.299 _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 N1A .53265(19) .63080(15) .42692(9) .0386(4) Uani d . 1 . . N C2A .4072(2) .60316(18) .44189(11) .0367(5) Uani d . 1 . . C C3A .3514(2) .48748(19) .42315(11) .0409(5) Uani d . 1 . . C H3AA .2631 .4712 .4342 .049 Uiso calc R 1 . . H C4A .4253(2) .39687(18) .38846(11) .0369(5) Uani d . 1 . . C C5A .6637(2) .34091(18) .34834(11) .0395(5) Uani d . 1 . . C N6A .78431(19) .37349(16) .33115(10) .0431(4) Uani d . 1 . . N C7A .8199(2) .49061(19) .34011(11) .0391(5) Uani d . 1 . . C C8A .7408(2) .57784(19) .37644(12) .0397(5) Uani d . 1 . . C C9A .6087(2) .54346(18) .39398(11) .0363(5) Uani d . 1 . . C C10A .5626(2) .42409(18) .37572(11) .0366(5) Uani d . 1 . . C N11A .6407(2) .22192(16) .33947(11) .0521(5) Uani d . 1 . . N H11A .7027 .1741 .3237 .062 Uiso calc R 1 . . H H11B .5642 .1943 .3496 .062 Uiso calc R 1 . . H C12A .7843(2) .6991(2) .39812(13) .0460(6) Uani d . 1 . . C N13A .8164(2) .7968(2) .41740(14) .0661(7) Uani d . 1 . . N N14A .9379(2) .51379(17) .31316(11) .0468(5) Uani d . 1 . . N C15A 1.0219(3) .4180(2) .27946(14) .0534(6) Uani d . 1 . . C H15A .9656 .3646 .2437 .064 Uiso calc R 1 . . H H15B 1.0654 .3728 .3125 .064 Uiso calc R 1 . . H C16A 1.1300(3) .4844(3) .24926(15) .0606(7) Uani d . 1 . . C H16A 1.2109 .5060 .2822 .073 Uiso calc R 1 . . H H16B 1.1588 .4369 .2079 .073 Uiso calc R 1 . . H C17A 1.0550(3) .5931(3) .23338(15) .0618(7) Uani d . 1 . . C H17A .9938 .5746 .1909 .074 Uiso calc R 1 . . H H17B 1.1201 .6558 .2297 .074 Uiso calc R 1 . . H C18A .9724(3) .6285(2) .29496(14) .0526(6) Uani d . 1 . . C H18A 1.0281 .6784 .3326 .063 Uiso calc R 1 . . H H18B .8892 .6700 .2826 .063 Uiso calc R 1 . . H C19A .3251(2) .70335(19) .47436(11) .0406(5) Uani d . 1 . . C C20A .3815(3) .8183(2) .48766(12) .0480(6) Uani d . 1 . . C H20A .4731 .8306 .4798 .058 Uiso calc R 1 . . H C21A .3036(3) .9144(2) .51242(13) .0567(7) Uani d . 1 . . C H21A .3424 .9907 .5200 .068 Uiso calc R 1 . . H C22A .1692(3) .8976(3) .52587(14) .0654(8) Uani d . 1 . . C H22A .1166 .9623 .5420 .078 Uiso calc R 1 . . H C23A .1131(3) .7845(3) .51526(17) .0742(9) Uani d . 1 . . C H23A .0229 .7727 .5254 .089 Uiso calc R 1 . . H C24A .1899(3) .6875(2) .48947(15) .0615(7) Uani d . 1 . . C H24A .1505 .6115 .4823 .074 Uiso calc R 1 . . H C25A .3488(2) .28285(19) .36055(11) .0384(5) Uani d . 1 . . C C26A .2800(2) .2217(2) .40239(12) .0433(5) Uani d . 1 . . C H26A .2920 .2466 .4498 .052 Uiso calc R 1 . . H C27A .1938(2) .1241(2) .37462(13) .0463(6) Uani d . 1 . . C H27A .1501 .0829 .4033 .056 Uiso calc R 1 . . H C28A .1733(2) .08867(19) .30392(13) .0439(5) Uani d . 1 . . C C29A .2429(3) .1482(2) .26162(12) .0469(6) Uani d . 1 . . C H29A .2303 .1235 .2142 .056 Uiso calc R 1 . . H C30A .3302(2) .24324(19) .28930(12) .0434(5) Uani d . 1 . . C H30A .3773 .2816 .2605 .052 Uiso calc R 1 . . H O31A .08819(19) -.00411(15) .27040(10) .0605(5) Uani d . 1 . . O C32A .0017(3) -.0587(3) .31025(18) .0813(10) Uani d . 1 . . C H32A -.0523 -.1219 .2810 .122 Uiso calc R 1 . . H H32B -.0592 -.0009 .3316 .122 Uiso calc R 1 . . H H32C .0583 -.0902 .3451 .122 Uiso calc R 1 . . H N1B .64357(19) .44952(16) .05103(10) .0405(4) Uani d . 1 . . N C2B .6878(2) .4204(2) -.01062(11) .0395(5) Uani d . 1 . . C C3B .7610(2) .5015(2) -.04031(12) .0428(5) Uani d . 1 . . C H3BA .7828 .4803 -.0853 .051 Uiso calc R 1 . . H C4B .8008(2) .6120(2) -.00334(12) .0399(5) Uani d . 1 . . C C5B .8013(2) .7481(2) .11500(12) .0425(5) Uani d . 1 . . C N6B .7371(2) .78003(17) .17107(10) .0447(5) Uani d . 1 . . N C7B .6392(2) .7071(2) .18735(11) .0403(5) Uani d . 1 . . C C8B .6187(2) .5900(2) .15132(11) .0411(5) Uani d . 1 . . C C9B .6748(2) .55964(19) .08738(11) .0375(5) Uani d . 1 . . C C10B .7616(2) .64258(19) .06452(11) .0379(5) Uani d . 1 . . C N11B .9099(2) .81845(19) .10906(12) .0594(6) Uani d . 1 . . N H11C .9331 .8791 .1404 .071 Uiso calc R 1 . . H H11D .9560 .8027 .0739 .071 Uiso calc R 1 . . H C12B .5482(3) .4975(2) .17517(13) .0532(6) Uani d . 1 . . C N13B .4959(3) .4202(2) .19378(14) .0871(9) Uani d . 1 . . N N14B .5698(2) .75498(18) .24073(10) .0468(5) Uani d . 1 . . N C15B .5943(3) .8782(2) .27611(13) .0541(6) Uani d . 1 . . C H15C .5719 .9336 .2450 .065 Uiso calc R 1 . . H H15D .6901 .8917 .2958 .065 Uiso calc R 1 . . H C16B .4965(3) .8901(3) .33170(14) .0629(7) Uani d . 1 . . C H16C .5413 .8671 .3732 .075 Uiso calc R 1 . . H H16D .4657 .9710 .3426 .075 Uiso calc R 1 . . H C17B .3759(3) .8068(3) .30127(13) .0575(7) Uani d . 1 . . C H17C .3105 .8442 .2719 .069 Uiso calc R 1 . . H H17D .3279 .7819 .3371 .069 Uiso calc R 1 . . H C18B .4441(2) .7022(2) .25983(12) .0489(6) Uani d . 1 . . C H18C .4674 .6416 .2874 .059 Uiso calc R 1 . . H H18D .3835 .6673 .2193 .059 Uiso calc R 1 . . H C19B .6570(2) .2959(2) -.04584(11) .0414(5) Uani d . 1 . . C C20B .5519(3) .2300(2) -.02590(13) .0498(6) Uani d . 1 . . C H20B .4996 .2649 .0087 .060 Uiso calc R 1 . . H C21B .5246(3) .1137(2) -.05683(15) .0605(7) Uani d . 1 . . C H21B .4535 .0710 -.0433 .073 Uiso calc R 1 . . H C22B .6022(3) .0599(2) -.10788(15) .0602(7) Uani d . 1 . . C H22B .5834 -.0185 -.1288 .072 Uiso calc R 1 . . H C23B .7080(3) .1238(2) -.12754(14) .0570(7) Uani d . 1 . . C H23B .7618 .0879 -.1612 .068 Uiso calc R 1 . . H C24B .7339(3) .2408(2) -.09721(12) .0491(6) Uani d . 1 . . C H24B .8042 .2836 -.1114 .059 Uiso calc R 1 . . H C25B .8831(2) .6913(2) -.03759(11) .0412(5) Uani d . 1 . . C C26B 1.0050(2) .6510(2) -.06407(11) .0417(5) Uani d . 1 . . C H26B 1.0334 .5748 -.0601 .050 Uiso calc R 1 . . H C27B 1.0856(3) .7203(2) -.09616(12) .0466(6) Uani d . 1 . . C H27B 1.1669 .6911 -.1133 .056 Uiso calc R 1 . . H C28B 1.0438(3) .8336(2) -.10246(12) .0485(6) Uani d . 1 . . C C29B .9217(3) .8752(2) -.07725(14) .0581(7) Uani d . 1 . . C H29B .8930 .9511 -.0817 .070 Uiso calc R 1 . . H C30B .8421(3) .8047(2) -.04560(14) .0555(7) Uani d . 1 . . C H30B .7598 .8335 -.0294 .067 Uiso calc R 1 . . H O31B 1.1158(2) .91008(17) -.13257(11) .0723(6) Uani d . 1 . . O C32B 1.2400(4) .8707(3) -.1606(2) .0923(12) Uani d . 1 . . C H32D 1.2794 .9328 -.1799 .138 Uiso calc R 1 . . H H32E 1.2197 .8022 -.1958 .138 Uiso calc R 1 . . H H32F 1.3050 .8502 -.1249 .138 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 .0389(10) .0355(10) .0405(10) .0010(8) .0092(8) .0015(8) C2A .0396(12) .0361(11) .0338(11) .0002(9) .0076(9) .0024(9) C3A .0382(12) .0397(12) .0442(12) -.0014(10) .0125(10) .0011(10) C4A .0426(12) .0344(11) .0353(11) -.0020(9) .0098(9) .0071(9) C5A .0443(12) .0323(11) .0433(12) .0015(9) .0115(10) .0066(9) N6A .0421(10) .0376(10) .0519(11) .0043(8) .0153(9) .0079(9) C7A .0358(11) .0379(12) .0450(12) .0010(9) .0090(10) .0083(10) C8A .0377(12) .0327(11) .0485(13) -.0015(9) .0085(10) .0047(10) C9A .0391(11) .0331(11) .0368(11) .0009(9) .0075(9) .0048(9) C10A .0391(12) .0355(11) .0363(11) .0020(9) .0102(9) .0060(9) N11A .0518(12) .0321(10) .0753(14) .0051(9) .0244(11) .0074(10) C12A .0366(12) .0417(14) .0597(15) .0000(10) .0124(11) .0049(11) N13A .0573(14) .0430(13) .0933(18) -.0088(11) .0147(13) -.0046(12) N14A .0413(10) .0403(11) .0618(12) .0022(8) .0199(10) .0086(9) C15A .0439(13) .0532(15) .0658(16) .0076(11) .0221(12) .0082(13) C16A .0454(14) .0756(19) .0645(17) .0046(13) .0222(13) .0136(14) C17A .0579(16) .0685(18) .0648(17) -.0038(14) .0203(14) .0195(14) C18A .0483(14) .0475(14) .0648(16) -.0046(11) .0155(12) .0124(12) C19A .0447(13) .0403(12) .0357(11) .0048(10) .0073(10) .0014(9) C20A .0573(15) .0426(13) .0443(13) .0033(11) .0155(12) .0023(11) C21A .080(2) .0412(14) .0476(14) .0100(13) .0144(14) .0004(11) C22A .0696(19) .0566(17) .0652(18) .0256(15) .0120(15) -.0057(14) C23A .0434(15) .075(2) .094(2) .0117(14) .0152(15) -.0191(17) C24A .0448(14) .0549(16) .0771(19) .0016(12) .0142(14) -.0145(14) C25A .0382(12) .0343(11) .0431(12) -.0002(9) .0105(10) .0039(9) C26A .0476(13) .0419(13) .0410(12) -.0030(10) .0119(10) .0048(10) C27A .0486(13) .0404(13) .0531(14) -.0056(11) .0178(11) .0098(11) C28A .0418(12) .0326(12) .0552(14) -.0012(10) .0117(11) -.0015(10) C29A .0605(15) .0369(12) .0417(12) -.0020(11) .0125(11) -.0012(10) C30A .0537(14) .0346(12) .0436(12) -.0026(10) .0169(11) .0050(10) O31A .0628(11) .0447(10) .0697(12) -.0176(9) .0136(10) -.0050(9) C32A .073(2) .070(2) .098(2) -.0354(17) .0261(18) -.0045(18) N1B .0397(10) .0403(10) .0449(10) .0036(8) .0128(8) .0121(8) C2B .0352(11) .0423(12) .0437(12) .0051(9) .0072(10) .0133(10) C3B .0459(13) .0447(13) .0402(12) .0034(10) .0107(10) .0106(10) C4B .0366(11) .0423(12) .0454(12) .0059(10) .0115(10) .0161(10) C5B .0400(12) .0424(13) .0486(13) .0035(10) .0132(10) .0126(10) N6B .0439(11) .0455(11) .0461(11) -.0022(9) .0136(9) .0073(9) C7B .0378(12) .0471(13) .0380(11) .0002(10) .0086(10) .0107(10) C8B .0407(12) .0435(13) .0427(12) .0023(10) .0114(10) .0135(10) C9B .0368(11) .0367(12) .0423(12) .0043(9) .0092(10) .0133(10) C10B .0371(11) .0370(12) .0430(12) .0054(9) .0113(10) .0124(10) N11B .0604(13) .0555(13) .0623(14) -.0179(11) .0279(11) -.0013(11) C12B .0654(16) .0496(15) .0483(14) -.0027(13) .0205(13) .0104(12) N13B .121(2) .0652(16) .0862(19) -.0168(16) .0513(18) .0203(14) N14B .0464(11) .0511(12) .0431(11) -.0041(9) .0136(9) .0038(9) C15B .0544(15) .0565(16) .0493(14) -.0028(12) .0147(12) -.0013(12) C16B .0612(17) .0713(19) .0543(16) .0063(15) .0190(14) -.0017(14) C17B .0497(15) .0749(18) .0504(14) .0073(13) .0180(12) .0108(13) C18B .0426(13) .0637(16) .0429(13) -.0006(12) .0126(11) .0118(11) C19B .0418(12) .0430(13) .0405(12) .0034(10) .0034(10) .0111(10) C20B .0462(13) .0466(14) .0587(15) .0032(11) .0135(12) .0102(12) C21B .0558(16) .0517(16) .0747(18) -.0045(13) .0100(14) .0116(14) C22B .0663(18) .0431(14) .0675(18) .0004(13) .0002(15) .0032(13) C23B .0692(18) .0482(15) .0533(15) .0122(13) .0121(13) .0041(12) C24B .0531(14) .0484(14) .0491(14) .0058(11) .0124(12) .0135(11) C25B .0470(13) .0401(12) .0405(12) .0034(10) .0119(10) .0139(10) C26B .0457(13) .0380(12) .0454(12) .0047(10) .0115(10) .0141(10) C27B .0455(13) .0490(14) .0491(13) .0012(11) .0149(11) .0137(11) C28B .0563(15) .0447(13) .0494(14) -.0060(11) .0112(12) .0192(11) C29B .0686(17) .0426(14) .0722(17) .0110(13) .0209(15) .0267(13) C30B .0551(15) .0494(15) .0713(17) .0152(12) .0263(13) .0243(13) O31B .0846(14) .0583(12) .0856(14) -.0068(10) .0329(12) .0316(10) C32B .094(2) .085(2) .109(3) -.025(2) .054(2) .023(2) 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 . 1.328(3) y N1A C9A . 1.359(3) y C2A C3A . 1.401(3) ? C2A C19A . 1.490(3) ? C3A C4A . 1.385(3) y C4A C10A . 1.421(3) ? C4A C25A . 1.488(3) ? C5A N6A . 1.319(3) y C5A N11A . 1.357(3) y C5A C10A . 1.449(3) ? N6A C7A . 1.359(3) y C7A N14A . 1.354(3) y C7A C8A . 1.404(3) ? C8A C12A . 1.428(3) ? C8A C9A . 1.429(3) ? C9A C10A . 1.409(3) ? C12A N13A . 1.147(3) ? N14A C18A . 1.466(3) y N14A C15A . 1.475(3) y C15A C16A . 1.519(3) ? C16A C17A . 1.508(4) ? C17A C18A . 1.525(3) ? C19A C24A . 1.390(3) ? C19A C20A . 1.393(3) ? C20A C21A . 1.385(3) ? C21A C22A . 1.373(4) ? C22A C23A . 1.375(4) ? C23A C24A . 1.391(3) ? C25A C26A . 1.390(3) ? C25A C30A . 1.401(3) ? C26A C27A . 1.390(3) ? C27A C28A . 1.385(3) ? C28A O31A . 1.372(3) ? C28A C29A . 1.390(3) ? C29A C30A . 1.373(3) ? O31A C32A . 1.421(3) ? N1B C2B . 1.326(3) y N1B C9B . 1.355(3) y C2B C3B . 1.407(3) ? C2B C19B . 1.488(3) ? C3B C4B . 1.379(3) y C4B C10B . 1.422(3) ? C4B C25B . 1.497(3) ? C5B N6B . 1.327(3) y C5B N11B . 1.348(3) y C5B C10B . 1.451(3) ? N6B C7B . 1.359(3) y C7B N14B . 1.349(3) y C7B C8B . 1.408(3) ? C8B C9B . 1.420(3) ? C8B C12B . 1.429(3) ? C9B C10B . 1.425(3) ? C12B N13B . 1.150(3) ? N14B C18B . 1.468(3) y N14B C15B . 1.469(3) y C15B C16B . 1.515(3) ? C16B C17B . 1.509(4) ? C17B C18B . 1.524(3) ? C19B C24B . 1.388(3) ? C19B C20B . 1.392(3) ? C20B C21B . 1.377(4) ? C21B C22B . 1.383(4) ? C22B C23B . 1.381(4) ? C23B C24B . 1.381(3) ? C25B C26B . 1.388(3) ? C25B C30B . 1.390(3) ? C26B C27B . 1.384(3) ? C27B C28B . 1.383(3) ? C28B O31B . 1.367(3) ? C28B C29B . 1.385(4) ? C29B C30B . 1.381(3) ? O31B C32B . 1.419(4) ?