#------------------------------------------------------------------------------ #$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $ #$Revision: 14 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2011828.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_2011828 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 281 _journal_page_last 283 _publ_section_title ; 5,12-Dimethyl-3,10-diphenyl-1,3,4,9,11,12-hexaazatetracyclo[6.6.1.0^2,6^. 0^9,13^]pentadeca-2(6),4,9(13),11-tetraene. A new Tr\"oger's base analogue ; loop_ _publ_author_name 'Moreno-Fuquen, Rodolfo' 'Abonia, Rodrigo' 'Valderrama-Naranjo, Jaime' 'Albornoz, Andrea' 'Mariezcurrena, Raul' _chemical_formula_moiety 'C23 H22 N6' _chemical_formula_sum 'C23 H22 N6' _chemical_formula_weight 382.46 _chemical_melting_point 393 _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 11.2240(10) _cell_length_b 13.6500(10) _cell_length_c 14.1100(10) _cell_angle_alpha 75.270(2) _cell_angle_beta 73.070(2) _cell_angle_gamma 76.270(2) _cell_volume 1968.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _exptl_crystal_density_diffrn 1.290 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 N1 .16530(16) .88309(13) .43637(13) .0482(4) Uani d . 1 . . N N2 .22728(17) .95533(15) .44375(14) .0565(5) Uani d . 1 . . N C3 .2711(2) 1.00200(18) .34865(18) .0532(5) Uani d . 1 . . C C3A .23639(18) .96234(16) .27955(16) .0456(5) Uani d . 1 . . C C4 .25174(19) .98986(17) .16708(16) .0489(5) Uani d . 1 . . C H41 .2332 1.0640 .1455 .053(6) Uiso calc R 1 . . H H42 .3384 .9658 .1330 .057(6) Uiso calc R 1 . . H N5 .16390(15) .94134(13) .13979(12) .0469(4) Uani d . 1 . . N C5A .03748(18) .99199(15) .16578(14) .0421(5) Uani d . 1 . . C N6 -.01459(15) 1.08203(13) .11151(12) .0459(4) Uani d . 1 . . N N7 -.13973(16) 1.11021(14) .15972(13) .0496(4) Uani d . 1 . . N C8 -.16285(18) 1.03730(16) .24076(15) .0456(5) Uani d . 1 . . C C8A -.05489(18) .96013(15) .24827(15) .0429(5) Uani d . 1 . . C C9 -.02889(18) .86386(16) .32385(16) .0469(5) Uani d . 1 . . C H91 -.0623 .8776 .3917 .045(5) Uiso calc R 1 . . H H92 -.0702 .8116 .3179 .048(5) Uiso calc R 1 . . H N10 .11016(15) .82642(12) .30538(12) .0452(4) Uani d . 1 . . N C10A .16926(18) .88772(15) .33821(15) .0425(5) Uani d . 1 . . C C15 .1670(2) .83437(16) .19604(16) .0504(5) Uani d . 1 . . C H151 .2542 .7990 .1859 .043(5) Uiso calc R 1 . . H H152 .1221 .7999 .1688 .059(6) Uiso calc R 1 . . H C16 .3433(3) 1.0882(2) .3274(2) .0784(8) Uani d . 1 . . C H161 .3632 1.0913 .3881 .144(14) Uiso calc R 1 . . H H162 .2926 1.1522 .3041 .168(18) Uiso calc R 1 . . H H163 .4202 1.0760 .2763 .152(16) Uiso calc R 1 . . H C17 -.2905(2) 1.04182(18) .31298(18) .0572(6) Uani d . 1 . . C H171 -.3441 1.1053 .2925 .064(7) Uiso calc R 1 . . H H172 -.2823 1.0381 .3797 .091(9) Uiso calc R 1 . . H H173 -.3272 .9850 .3131 .076(8) Uiso calc R 1 . . H C18 .10585(19) .81778(17) .52437(15) .0475(5) Uani d . 1 . . C C19 .0415(2) .8563(2) .61018(18) .0630(6) Uani d . 1 . . C H19 .0376 .9248 .6114 .084(9) Uiso calc R 1 . . H C20 -.0168(3) .7921(3) .6940(2) .0784(8) Uani d . 1 . . C H20 -.0584 .8169 .7528 .083(8) Uiso calc R 1 . . H C21 -.0143(3) .6921(3) .6917(2) .0791(8) Uani d . 1 . . C H21 -.0568 .6500 .7479 .095(9) Uiso calc R 1 . . H C22 .0515(2) .6539(2) .60580(19) .0719(7) Uani d . 1 . . C H22 .0539 .5856 .6045 .070(8) Uiso calc R 1 . . H C23 .1133(2) .71577(18) .52235(17) .0583(6) Uani d . 1 . . C H23 .1597 .6895 .4652 .085(8) Uiso calc R 1 . . H C24 .03833(19) 1.14399(17) .01828(15) .0465(5) Uani d . 1 . . C C25 .1455(2) 1.1038(2) -.04826(16) .0593(6) Uani d . 1 . . C H25 .1846 1.0357 -.0322 .073(8) Uiso calc R 1 . . H C26 .1936(3) 1.1663(2) -.13895(17) .0676(7) Uani d . 1 . . C H26 .2663 1.1401 -.1834 .089(9) Uiso calc R 1 . . H C27 .1353(3) 1.2667(2) -.16430(19) .0696(7) Uani d . 1 . . C H27 .1687 1.3083 -.2251 .084(8) Uiso calc R 1 . . H C28 .0271(3) 1.3048(2) -.09863(19) .0717(7) Uani d . 1 . . C H28 -.0138 1.3720 -.1162 .103(10) Uiso calc R 1 . . H C29 -.0216(2) 1.24479(18) -.00716(18) .0602(6) Uani d . 1 . . C H29 -.0940 1.2717 .0371 .076 Uiso calc R 1 . . H N31 .64128(16) .37172(13) .04055(12) .0490(4) Uani d . 1 . . N N32 .70257(18) .44389(14) -.03196(13) .0570(5) Uani d . 1 . . N C33 .7494(2) .48927(17) .01786(16) .0546(6) Uani d . 1 . . C C33A .71959(19) .44904(15) .12253(15) .0473(5) Uani d . 1 . . C C34 .7416(2) .47491(17) .21237(16) .0500(5) Uani d . 1 . . C H341 .8290 .4492 .2154 .051(6) Uiso calc R 1 . . H H342 .7255 .5490 .2061 .058(6) Uiso calc R 1 . . H N35 .65622(16) .42776(12) .30635(12) .0456(4) Uani d . 1 . . N C35A .53044(19) .48049(15) .31739(14) .0430(5) Uani d . 1 . . C N36 .48362(16) .57113(13) .35117(12) .0464(4) Uani d . 1 . . N N37 .35803(16) .60266(14) .34987(14) .0528(5) Uani d . 1 . . N C38 .3283(2) .53033(17) .31812(15) .0492(5) Uani d . 1 . . C C38A .43365(19) .45174(15) .29628(14) .0452(5) Uani d . 1 . . C C39 .4540(2) .35577(16) .25608(16) .0493(5) Uani d . 1 . . C H391 .4123 .3043 .3078 .055(6) Uiso calc R 1 . . H H392 .4175 .3709 .1984 .045(5) Uiso calc R 1 . . H N40 .59152(16) .31553(12) .22529(12) .0462(4) Uani d . 1 . . N C40A .65002(18) .37518(15) .13366(14) .0429(5) Uani d . 1 . . C C45 .6547(2) .32114(15) .30189(16) .0510(5) Uani d . 1 . . C H451 .6115 .2870 .3678 .053(6) Uiso calc R 1 . . H H452 .7411 .2844 .2866 .046(6) Uiso calc R 1 . . H C46 .8210(3) .5756(2) -.0379(2) .0776(8) Uani d . 1 . . C H461 .9102 .5493 -.0511 .129(13) Uiso calc R 1 . . H H462 .8007 .6270 .0025 .140(14) Uiso calc R 1 . . H H463 .7977 .6057 -.1008 .126(13) Uiso calc R 1 . . H C47 .1978(2) .5399(2) .3060(2) .0674(7) Uani d . 1 . . C H471 .1445 .5989 .3309 .116(11) Uiso calc R 1 . . H H472 .1641 .4791 .3435 .109(11) Uiso calc R 1 . . H H473 .2009 .5480 .2357 .115(11) Uiso calc R 1 . . H C48 .58348(19) .30512(16) .01262(14) .0450(5) Uani d . 1 . . C C49 .5254(2) .34092(19) -.06645(17) .0588(6) Uani d . 1 . . C H49 .5252 .4083 -.1024 .081(8) Uiso calc R 1 . . H C50 .4674(2) .2755(2) -.0917(2) .0692(7) Uani d . 1 . . C H50 .4289 .2989 -.1454 .106(10) Uiso calc R 1 . . H C51 .4664(2) .1768(2) -.03826(19) .0641(6) Uani d . 1 . . C H51 .4246 .1341 -.0540 .077(8) Uiso calc R 1 . . H C52 .5268(2) .14081(19) .03842(19) .0628(6) Uani d . 1 . . C H52 .5273 .0732 .0738 .072(8) Uiso calc R 1 . . H C53 .5872(2) .20394(17) .06376(17) .0571(6) Uani d . 1 . . C H53 .6300 .1787 .1148 .063(7) Uiso calc R 1 . . H C54 .5431(2) .63194(16) .38489(15) .0461(5) Uani d . 1 . . C C55 .6505(2) .58929(18) .42038(16) .0557(6) Uani d . 1 . . C H55 .6849 .5199 .4230 .056(6) Uiso calc R 1 . . H C56 .7061(2) .6517(2) .45198(17) .0647(6) Uani d . 1 . . C H56 .7797 .6241 .4741 .057(7) Uiso calc R 1 . . H C57 .6541(3) .7537(2) .45109(18) .0691(7) Uani d . 1 . . C H57 .6921 .7947 .4728 .081(8) Uiso calc R 1 . . H C58 .5465(3) .7943(2) .4182(2) .0715(7) Uani d . 1 . . C H58 .5107 .8631 .4183 .081(8) Uiso calc R 1 . . H C59 .4902(2) .73471(18) .38497(19) .0621(6) Uani d . 1 . . C H59 .4169 .7632 .3626 .089(9) 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 N1 .0530(10) .0521(10) .0455(10) -.0106(8) -.0158(8) -.0148(8) N2 .0589(11) .0630(12) .0592(12) -.0159(9) -.0196(9) -.0220(10) C3 .0492(13) .0587(13) .0584(14) -.0119(11) -.0169(11) -.0167(11) C3A .0371(11) .0516(12) .0507(12) -.0068(9) -.0098(9) -.0167(10) C4 .0391(11) .0570(14) .0492(12) -.0087(10) -.0041(9) -.0157(10) N5 .0458(10) .0520(10) .0436(10) -.0057(8) -.0090(8) -.0161(8) C5A .0417(11) .0499(12) .0386(10) -.0078(9) -.0119(9) -.0134(9) N6 .0417(10) .0555(11) .0388(9) -.0092(8) -.0093(7) -.0067(8) N7 .0420(10) .0586(11) .0452(10) -.0089(8) -.0092(8) -.0070(9) C8 .0409(11) .0528(12) .0454(12) -.0102(10) -.0106(9) -.0120(10) C8A .0426(11) .0486(11) .0415(11) -.0109(9) -.0132(9) -.0096(9) C9 .0445(11) .0533(12) .0483(12) -.0148(10) -.0135(9) -.0115(10) N10 .0483(10) .0434(9) .0475(10) -.0057(8) -.0143(8) -.0148(8) C10A .0394(11) .0451(11) .0444(11) -.0031(9) -.0114(9) -.0143(9) C15 .0558(13) .0502(12) .0507(12) -.0021(10) -.0166(10) -.0225(10) C16 .0801(19) .091(2) .083(2) -.0428(17) -.0240(17) -.0212(17) C17 .0461(12) .0605(15) .0586(15) -.0086(11) -.0086(11) -.0064(11) C18 .0427(11) .0566(13) .0429(11) -.0033(10) -.0128(9) -.0122(10) C19 .0638(15) .0714(17) .0538(14) .0002(13) -.0118(12) -.0268(12) C20 .0710(18) .105(2) .0486(15) .0000(16) -.0019(13) -.0263(16) C21 .0676(17) .101(2) .0522(16) -.0178(16) -.0018(13) .0003(16) C22 .0769(18) .0659(17) .0634(17) -.0144(14) -.0076(14) -.0058(13) C23 .0643(15) .0568(14) .0474(13) -.0069(11) -.0040(11) -.0135(11) C24 .0506(12) .0576(13) .0371(11) -.0209(10) -.0115(9) -.0084(10) C25 .0600(14) .0760(17) .0417(12) -.0167(13) -.0060(11) -.0145(12) C26 .0684(16) .099(2) .0412(13) -.0339(15) -.0041(12) -.0170(14) C27 .0890(19) .0847(19) .0454(14) -.0509(16) -.0131(14) -.0018(14) C28 .092(2) .0659(17) .0580(16) -.0326(15) -.0165(15) .0013(13) C29 .0660(15) .0606(15) .0542(14) -.0193(12) -.0118(12) -.0079(11) N31 .0597(11) .0488(10) .0369(9) -.0153(9) -.0059(8) -.0071(8) N32 .0692(12) .0582(11) .0385(10) -.0214(10) -.0015(9) -.0050(9) C33 .0591(14) .0548(13) .0444(12) -.0171(11) .0002(10) -.0088(10) C33A .0516(12) .0437(11) .0425(12) -.0081(10) -.0050(9) -.0095(9) C34 .0488(13) .0488(13) .0508(12) -.0102(10) -.0073(10) -.0115(10) N35 .0535(10) .0428(9) .0403(9) -.0069(8) -.0118(8) -.0091(7) C35A .0524(12) .0386(10) .0349(10) -.0087(9) -.0054(9) -.0074(8) N36 .0484(10) .0462(10) .0445(10) -.0069(8) -.0077(8) -.0145(8) N37 .0501(11) .0530(11) .0556(11) -.0057(9) -.0099(9) -.0182(9) C38 .0519(13) .0528(12) .0405(11) -.0128(10) -.0035(9) -.0108(10) C38A .0521(12) .0448(11) .0371(11) -.0143(10) -.0033(9) -.0085(9) C39 .0561(13) .0492(12) .0425(11) -.0179(10) -.0040(10) -.0104(10) N40 .0592(11) .0389(9) .0378(9) -.0096(8) -.0080(8) -.0068(7) C40A .0488(12) .0393(10) .0366(11) -.0040(9) -.0065(9) -.0087(9) C45 .0660(14) .0404(11) .0414(12) -.0046(10) -.0125(10) -.0044(9) C46 .094(2) .0782(18) .0554(16) -.0438(16) .0040(14) -.0025(15) C47 .0526(14) .0811(18) .0730(18) -.0118(14) -.0129(12) -.0262(15) C48 .0474(12) .0473(12) .0374(11) -.0040(9) -.0069(9) -.0113(9) C49 .0626(15) .0556(14) .0546(14) -.0038(11) -.0193(12) -.0054(11) C50 .0687(16) .0806(19) .0640(16) -.0003(14) -.0317(14) -.0188(14) C51 .0580(14) .0746(17) .0673(16) -.0109(13) -.0164(12) -.0270(14) C52 .0806(17) .0509(14) .0613(15) -.0137(12) -.0188(13) -.0155(12) C53 .0769(16) .0488(13) .0490(13) -.0074(11) -.0244(12) -.0086(10) C54 .0542(13) .0467(12) .0360(11) -.0155(10) -.0033(9) -.0087(9) C55 .0727(16) .0537(14) .0449(12) -.0158(12) -.0170(11) -.0094(10) C56 .0716(17) .0797(18) .0497(14) -.0219(14) -.0187(12) -.0124(12) C57 .0846(19) .0738(18) .0574(15) -.0386(15) -.0015(13) -.0236(13) C58 .0798(19) .0551(15) .0827(19) -.0213(14) -.0073(15) -.0251(14) C59 .0645(15) .0510(14) .0719(16) -.0137(12) -.0100(13) -.0190(12) 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 N1 C10A . 1.358(3) ? N1 N2 . 1.374(2) ? N1 C18 . 1.421(3) ? N2 C3 . 1.333(3) ? C3 C3A . 1.409(3) ? C3 C16 . 1.504(3) ? C3A C10A . 1.365(3) ? C3A C4 . 1.503(3) ? C4 N5 . 1.490(3) yes C4 H41 . .9700 ? C4 H42 . .9700 ? N5 C5A . 1.409(2) yes N5 C15 . 1.472(3) yes C5A C8A . 1.368(3) ? C5A N6 . 1.371(3) ? N6 N7 . 1.380(2) ? N6 C24 . 1.420(2) ? N7 C8 . 1.318(3) ? C8 C8A . 1.415(3) ? C8 C17 . 1.495(3) ? C8A C9 . 1.495(3) ? C9 N10 . 1.489(2) yes C9 H91 . .9700 ? C9 H92 . .9700 ? N10 C10A . 1.412(2) yes N10 C15 . 1.474(3) yes C15 H151 . .9700 ? C15 H152 . .9700 ? C16 H161 . .9600 ? C16 H162 . .9600 ? C16 H163 . .9600 ? C17 H171 . .9600 ? C17 H172 . .9600 ? C17 H173 . .9600 ? C18 C19 . 1.378(3) ? C18 C23 . 1.382(3) ? C19 C20 . 1.374(4) ? C19 H19 . .9300 ? C20 C21 . 1.366(4) ? C20 H20 . .9300 ? C21 C22 . 1.380(4) ? C21 H21 . .9300 ? C22 C23 . 1.371(3) ? C22 H22 . .9300 ? C23 H23 . .9300 ? C24 C25 . 1.385(3) ? C24 C29 . 1.387(3) ? C25 C26 . 1.385(3) ? C25 H25 . .9300 ? C26 C27 . 1.376(4) ? C26 H26 . .9300 ? C27 C28 . 1.376(4) ? C27 H27 . .9300 ? C28 C29 . 1.378(3) ? C28 H28 . .9300 ? C29 H29 . .9300 ? N31 C40A . 1.359(2) ? N31 N32 . 1.375(2) ? N31 C48 . 1.419(3) ? N32 C33 . 1.321(3) ? C33 C33A . 1.408(3) ? C33 C46 . 1.504(3) ? C33A C40A . 1.368(3) ? C33A C34 . 1.498(3) ? C34 N35 . 1.487(3) yes C34 H341 . .9700 ? C34 H342 . .9700 ? N35 C35A . 1.408(3) yes N35 C45 . 1.477(3) yes C35A C38A . 1.369(3) ? C35A N36 . 1.371(2) ? N36 N37 . 1.377(2) ? N36 C54 . 1.418(3) ? N37 C38 . 1.325(3) ? C38 C38A . 1.414(3) ? C38 C47 . 1.495(3) ? C38A C39 . 1.500(3) ? C39 N40 . 1.484(3) yes C39 H391 . .9700 ? C39 H392 . .9700 ? N40 C40A . 1.410(2) yes N40 C45 . 1.480(3) yes C45 H451 . .9700 ? C45 H452 . .9700 ? C46 H461 . .9600 ? C46 H462 . .9600 ? C46 H463 . .9600 ? C47 H471 . .9600 ? C47 H472 . .9600 ? C47 H473 . .9600 ? C48 C49 . 1.379(3) ? C48 C53 . 1.383(3) ? C49 C50 . 1.386(3) ? C49 H49 . .9300 ? C50 C51 . 1.367(4) ? C50 H50 . .9300 ? C51 C52 . 1.368(3) ? C51 H51 . .9300 ? C52 C53 . 1.380(3) ? C52 H52 . .9300 ? C53 H53 . .9300 ? C54 C55 . 1.384(3) ? C54 C59 . 1.387(3) ? C55 C56 . 1.386(3) ? C55 H55 . .9300 ? C56 C57 . 1.374(4) ? C56 H56 . .9300 ? C57 C58 . 1.364(4) ? C57 H57 . .9300 ? C58 C59 . 1.375(3) ? C58 H58 . .9300 ? C59 H59 . .9300 ?