data_2011424 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2000 _journal_volume 56 _journal_page_first 1265 _journal_page_last 1266 _publ_section_title ; Terbogrel, a dual-acting agent for thromboxane receptor antagonism and thromboxane synthase inhibition ; loop_ _publ_author_name 'Michaux, Catherine' 'Norberg, Bernadette' "Dogn\'e , Jean-Michel" 'Durant, Fran\,cois' 'Masereel, Bernard' 'Delarge, Jacques' 'Wouters, Johan' _chemical_name_common terbogrel _chemical_formula_sum 'C23 H27 N5 O2' _chemical_formula_weight 405.50 _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 14.9340(10) _cell_length_b 10.1150(10) _cell_length_c 15.7400(10) _cell_angle_alpha 90.00 _cell_angle_beta 113.049(5) _cell_angle_gamma 90.00 _cell_volume 2187.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.231 _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 C1 1.08328(15) .0187(2) .88663(13) .0763(6) Uani d . 1 . . C H1A 1.0424 -.0566 .8819 .114 Uiso calc R 1 . . H H1B 1.1264 .0312 .9499 .114 Uiso calc R 1 . . H H1C 1.1207 .0042 .8499 .114 Uiso calc R 1 . . H C2 1.08166(13) .26184(19) .85382(13) .0662(5) Uani d . 1 . . C H2A 1.1160 .2471 .8144 .099 Uiso calc R 1 . . H H2B 1.1275 .2773 .9158 .099 Uiso calc R 1 . . H H2C 1.0400 .3375 .8324 .099 Uiso calc R 1 . . H C3 .96335(13) .1680(2) .91192(11) .0662(5) Uani d . 1 . . C H3A .9213 .2426 .8877 .099 Uiso calc R 1 . . H H3B 1.0077 .1866 .9740 .099 Uiso calc R 1 . . H H3C .9249 .0918 .9118 .099 Uiso calc R 1 . . H C4 1.02051(10) .14085(15) .85219(9) .0442(3) Uani d . 1 . . C N5 .94693(8) .12065(12) .75740(7) .0399(3) Uani d . 1 . . N H5 .8880(12) .1047(15) .7519(11) .049(4) Uiso d . 1 . . H C6 .96475(9) .10485(13) .68113(9) .0366(3) Uani d . 1 . . C N7 1.05604(8) .09022(13) .69011(8) .0465(3) Uani d . 1 . . N C8 1.07929(9) .07551(16) .61872(10) .0458(3) Uani d . 1 . . C N9 1.11025(10) .05886(18) .56317(10) .0680(4) Uani d . 1 . . N N10 .88886(8) .10299(12) .59729(8) .0405(3) Uani d . 1 . . N H10 .9001(11) .0617(16) .5535(12) .053(4) Uiso d . 1 . . H C11 .78889(9) .12373(12) .57780(8) .0336(3) Uani d . 1 . . C C12 .72172(9) .04607(13) .50961(9) .0388(3) Uani d . 1 . . C H12 .7430 -.0177 .4792 .047 Uiso calc R 1 . . H C13 .62338(10) .06382(14) .48710(9) .0431(3) Uani d . 1 . . C H13 .5786 .0133 .4403 .052 Uiso calc R 1 . . H C14 .59069(9) .15601(14) .53340(9) .0394(3) Uani d . 1 . . C H14 .5244 .1653 .5189 .047 Uiso calc R 1 . . H C15 .65697(9) .23481(12) .60165(8) .0333(3) Uani d . 1 . . C C16 .75602(9) .22091(12) .62122(8) .0348(3) Uani d . 1 . . C H16 .8005 .2772 .6637 .042 Uiso calc R 1 . . H C17 .62346(9) .33251(12) .65423(9) .0356(3) Uani d . 1 . . C C18 .64529(9) .47432(12) .64555(9) .0358(3) Uani d . 1 . . C C19 .63575(10) .52835(14) .56121(10) .0451(3) Uani d . 1 . . C H19 .6190 .4746 .5093 .054 Uiso calc R 1 . . H C20 .65116(12) .66165(15) .55459(11) .0528(4) Uani d . 1 . . C H20 .6456 .6986 .4986 .063 Uiso calc R 1 . . H C21 .67480(11) .73887(15) .63193(11) .0515(4) Uani d . 1 . . C H21 .6837 .8291 .6269 .062 Uiso calc R 1 . . H N22 .68555(9) .68985(12) .71417(9) .0483(3) Uani d . 1 . . N C23 .67238(10) .56039(13) .72015(10) .0419(3) Uani d . 1 . . C H23 .6819 .5256 .7777 .050 Uiso calc R 1 . . H C24 .57394(10) .29827(14) .70536(10) .0413(3) Uani d . 1 . . C H24 .5541(11) .3688(15) .7359(11) .048(4) Uiso d . 1 . . H C25 .54620(10) .16305(14) .72486(10) .0432(3) Uani d . 1 . . C H25A .5679 .0983 .6916 .052 Uiso calc R 1 . . H H25B .4759 .1572 .7025 .052 Uiso calc R 1 . . H C26 .59052(11) .13039(14) .82789(10) .0456(3) Uani d . 1 . . C H26A .5778 .2027 .8621 .055 Uiso calc R 1 . . H H26B .5593 .0519 .8389 .055 Uiso calc R 1 . . H C27 .70013(11) .10697(14) .86361(10) .0489(3) Uani d . 1 . . C H27A .7313 .1847 .8515 .059 Uiso calc R 1 . . H H27B .7256 .0936 .9299 .059 Uiso calc R 1 . . H C28 .72410(10) -.01093(14) .81872(10) .0460(3) Uani d . 1 . . C O29 .76994(9) -.00641(12) .77071(9) .0641(3) Uani d . 1 . . O O30 .68680(10) -.12204(11) .83429(10) .0681(4) Uani d . 1 . . O H30 .698(2) -.196(3) .7966(19) .127(9) 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 C1 .0775(12) .0887(14) .0561(10) .0253(11) .0191(9) .0199(10) C2 .0621(10) .0753(12) .0648(11) -.0232(9) .0286(9) -.0221(9) C3 .0587(9) .1049(14) .0416(8) -.0106(10) .0268(7) -.0181(9) C4 .0399(7) .0580(8) .0352(7) -.0012(6) .0152(6) -.0050(6) N5 .0321(6) .0566(7) .0349(6) -.0010(5) .0172(5) -.0047(5) C6 .0343(6) .0419(7) .0372(6) .0017(5) .0178(5) -.0030(5) N7 .0339(6) .0701(8) .0398(6) .0033(5) .0191(5) -.0058(6) C8 .0324(6) .0650(9) .0422(7) .0033(6) .0169(6) -.0052(7) N9 .0510(8) .1096(12) .0530(8) .0066(8) .0306(7) -.0127(8) N10 .0340(6) .0563(7) .0350(6) .0059(5) .0177(5) -.0075(5) C11 .0330(6) .0386(6) .0326(6) .0019(5) .0166(5) .0008(5) C12 .0426(7) .0412(7) .0361(6) .0011(6) .0191(6) -.0055(5) C13 .0403(7) .0498(8) .0373(7) -.0068(6) .0132(6) -.0096(6) C14 .0316(6) .0477(7) .0392(7) .0000(5) .0142(5) -.0013(6) C15 .0343(6) .0339(6) .0344(6) .0030(5) .0164(5) .0020(5) C16 .0326(6) .0356(6) .0373(6) -.0012(5) .0151(5) -.0043(5) C17 .0321(6) .0374(7) .0380(6) .0052(5) .0146(5) -.0008(5) C18 .0315(6) .0380(7) .0409(7) .0073(5) .0174(5) .0016(5) C19 .0470(7) .0495(8) .0413(7) .0059(6) .0201(6) .0009(6) C20 .0595(9) .0515(9) .0512(8) .0077(7) .0257(7) .0146(7) C21 .0540(9) .0393(7) .0650(10) .0048(6) .0274(8) .0079(7) N22 .0529(7) .0399(6) .0564(7) .0013(5) .0261(6) -.0024(5) C23 .0460(7) .0399(7) .0435(7) .0026(6) .0215(6) .0001(6) C24 .0409(7) .0419(7) .0474(7) .0038(6) .0243(6) -.0034(6) C25 .0416(7) .0468(7) .0473(7) -.0057(6) .0240(6) -.0060(6) C26 .0568(8) .0439(7) .0466(8) -.0082(6) .0317(7) -.0079(6) C27 .0547(8) .0460(8) .0451(8) -.0106(6) .0185(7) -.0065(6) C28 .0457(7) .0458(8) .0479(8) -.0062(6) .0199(6) .0004(6) O29 .0725(7) .0606(7) .0773(8) -.0160(6) .0490(7) -.0096(6) O30 .0995(10) .0443(6) .0866(9) -.0130(6) .0646(8) -.0072(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 N10 C6 . 1.3621(17) ? N10 C11 . 1.4173(16) ? N10 H10 . .877(17) ? C18 C23 . 1.3887(18) ? C18 C19 . 1.3903(18) ? C18 C17 . 1.4892(18) ? C15 C14 . 1.3916(18) ? C15 C16 . 1.3950(17) ? C15 C17 . 1.4954(16) ? C24 C17 . 1.3344(18) ? C24 C25 . 1.4954(19) ? C24 H24 . .969(16) ? C16 C11 . 1.3916(16) ? C16 H16 . .9300 ? C11 C12 . 1.3901(18) ? C6 N7 . 1.3226(16) ? C6 N5 . 1.3371(16) ? N5 C4 . 1.4804(17) ? N5 H5 . .865(17) ? C4 C1 . 1.517(2) ? C4 C2 . 1.521(2) ? C4 C3 . 1.5219(19) ? N7 C8 . 1.3080(17) ? C14 C13 . 1.3848(19) ? C14 H14 . .9300 ? C13 C12 . 1.3810(19) ? C13 H13 . .9300 ? C23 N22 . 1.3330(18) ? C23 H23 . .9300 ? O29 C28 . 1.2028(17) ? O30 C28 . 1.3192(17) ? O30 H30 . 1.01(3) ? C12 H12 . .9300 ? C19 C20 . 1.379(2) ? C19 H19 . .9300 ? N22 C21 . 1.3359(19) ? C26 C27 . 1.527(2) ? C26 C25 . 1.529(2) ? C26 H26A . .9700 ? C26 H26B . .9700 ? N9 C8 . 1.1504(18) ? C25 H25A . .9700 ? C25 H25B . .9700 ? C28 C27 . 1.499(2) ? C21 C20 . 1.371(2) ? C21 H21 . .9300 ? C27 H27A . .9700 ? C27 H27B . .9700 ? C20 H20 . .9300 ? C2 H2A . .9600 ? C2 H2B . .9600 ? C2 H2C . .9600 ? C3 H3A . .9600 ? C3 H3B . .9600 ? C3 H3C . .9600 ? C1 H1A . .9600 ? C1 H1B . .9600 ? C1 H1C . .9600 ?