data_2012501 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2002 _journal_volume 58 _journal_page_first o125 _journal_page_last o128 _publ_section_title ; 2-(4-Bromophenyl)-1,2-dihydropyrimido[1,2-a]benzimidazol-4(3H)-one and 4-(4-methylphenyl)-3,4-dihydropyrimido[1,2-a]benzimidazol-2(1H)-one form hydrogen-bonded base-paired dimers ; loop_ _publ_author_name 'Low, John Nicolson' 'Cobo, Justo' 'Insuasty, Braulio' 'Nogueras, Manuel' 'Salcedo, Angela' "S\'anchez, Adolfo" _chemical_formula_moiety 'C17 H15 N3 O' _chemical_formula_sum 'C17 H15 N3 O' _chemical_formula_weight 277.32 _chemical_melting_point 506 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall 'p-1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1360(3) _cell_length_b 9.8647(4) _cell_length_c 10.0975(5) _cell_angle_alpha 114.8796(13) _cell_angle_beta 94.9156(15) _cell_angle_gamma 100.966(3) _cell_volume 709.18(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120.0(10) _exptl_crystal_density_diffrn 1.299 _diffrn_ambient_temperature 120.0(10) 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 .91899(12) .67969(12) .51394(12) .0258(3) Uani d . 1 . . N C2 .90560(16) .82721(16) .55341(15) .0266(3) Uani d . 1 A . C O2 1.01688(11) .93793(11) .64295(11) .0350(3) Uani d . 1 . . O C3 .75014(16) .84074(15) .47112(16) .0292(3) Uani d D 1 . . C C4A .58901(17) .71272(16) .43032(16) .0217(4) Uani d PD .907(4) A -1 C C41A .4544(3) .71274(19) .3174(3) .0205(4) Uani d P .907(4) A -1 C C42A .4750(2) .6777(2) .1723(3) .0272(5) Uani d P .907(4) A -1 C C43A .3473(4) .6760(2) .0706(2) .0293(6) Uani d P .907(4) A -1 C C44A .1950(4) .7105(4) .1112(3) .0263(7) Uani d P .907(4) A -1 C C45A .1757(3) .7467(3) .2567(3) .0273(6) Uani d P .907(4) A -1 C C46A .3029(3) .7475(2) .35847(19) .0229(5) Uani d P .907(4) A -1 C C47A .0573(3) .7103(2) .0022(3) .0411(5) Uani d P .907(4) A -1 C N5 .63728(12) .56436(12) .37319(12) .0222(3) Uani d D 1 . . N C5A .53518(16) .41306(15) .29563(14) .0229(3) Uani d . 1 A . C C6 .36396(16) .35199(16) .23039(15) .0305(4) Uani d . 1 . . C C7 .30616(18) .19275(16) .16268(17) .0339(4) Uani d . 1 A . C C8 .41401(17) .09745(16) .15937(15) .0309(4) Uani d . 1 . . C C9 .58416(17) .15874(16) .22647(14) .0263(3) Uani d . 1 A . C C9A .64417(15) .31836(15) .29690(14) .0217(3) Uani d . 1 . . C N10 .80576(13) .40885(13) .37738(12) .0251(3) Uani d . 1 A . N C10A .79250(15) .55081(15) .42150(14) .0217(3) Uani d . 1 A . C C4B .6609(15) .7020(14) .3331(15) .025(4) Uani d PD .093(4) A -2 C C41B .492(2) .710(2) .259(3) .019(4) Uani d PDU .093(4) A -2 C C42B .377(4) .735(2) .346(2) .017(4) Uani d PU .093(4) A -2 C C43B .215(3) .742(3) .292(3) .020(4) Uani d PU .093(4) A -2 C C44B .172(3) .712(4) .149(4) .013(4) Uani d PU .093(4) A -2 C C45B .280(4) .680(3) .070(3) .019(4) Uani d PU .093(4) A -2 C C46B .442(3) .684(2) .113(3) .022(4) Uani d PU .093(4) A -2 C C47B -.001(3) .714(3) .066(3) .058(7) Uani d P .093(4) A -2 C H1 1.0140 .6666 .5498 .031 Uiso calc R 1 . . H H3A .7780 .8435 .3786 .035 Uiso calc R 1 A . H H3B .7254 .9406 .5331 .035 Uiso calc R 1 . . H H4A .5416 .7282 .5223 .026 Uiso calc PR .907(4) A -1 H H42A .5779 .6547 .1422 .033 Uiso calc PR .907(4) A -1 H H43A .3638 .6509 -.0282 .035 Uiso calc PR .907(4) A -1 H H45A .0736 .7714 .2873 .033 Uiso calc PR .907(4) A -1 H H46A .2862 .7720 .4571 .028 Uiso calc PR .907(4) A -1 H H47A .1064 .7223 -.0787 .062 Uiso calc PR .4535(18) A -1 H H47B .0056 .7960 .0526 .062 Uiso calc PR .4535(18) A -1 H H47C -.0300 .6125 -.0384 .062 Uiso calc PR .4535(18) A -1 H H47D -.0517 .6982 .0357 .062 Uiso calc PR .4535(18) A -1 H H47E .0490 .6245 -.0956 .062 Uiso calc PR .4535(18) A -1 H H47F .0847 .8080 -.0046 .062 Uiso calc PR .4535(18) A -1 H H6 .2901 .4163 .2321 .037 Uiso calc R 1 A . H H7 .1896 .1470 .1171 .041 Uiso calc R 1 . . H H8 .3699 -.0114 .1102 .037 Uiso calc R 1 A . H H9 .6574 .0938 .2244 .032 Uiso calc R 1 . . H H4B .7392 .6852 .2597 .030 Uiso calc PR .093(4) A -2 H H42B .4037 .7477 .4448 .021 Uiso calc PR .093(4) A -2 H H43B .1355 .7676 .3571 .024 Uiso calc PR .093(4) A -2 H H45B .2448 .6496 -.0327 .023 Uiso calc PR .093(4) A -2 H H46B .5199 .6689 .0467 .026 Uiso calc PR .093(4) A -2 H H47G -.0869 .6187 .0421 .087 Uiso calc PR .0465(18) A -2 H H47H .0177 .7210 -.0255 .087 Uiso calc PR .0465(18) A -2 H H47I -.0397 .8030 .1309 .087 Uiso calc PR .0465(18) A -2 H H47J .0143 .8098 .0562 .087 Uiso calc PR .0465(18) A -2 H H47K -.0903 .7074 .1238 .087 Uiso calc PR .0465(18) A -2 H H47L -.0329 .6255 -.0326 .087 Uiso calc PR .0465(18) A -2 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 .0172(6) .0244(6) .0357(7) .0054(5) .0014(5) .0140(5) C2 .0216(7) .0258(8) .0345(8) .0060(6) .0059(6) .0151(7) O2 .0270(6) .0259(6) .0458(7) .0012(4) -.0021(5) .0140(5) C3 .0257(7) .0226(7) .0391(9) .0068(6) .0015(6) .0141(7) C4A .0221(8) .0201(8) .0248(9) .0073(6) .0050(6) .0107(6) C41A .0221(10) .0175(8) .0245(10) .0078(7) .0057(8) .0105(8) C42A .0298(10) .0318(10) .0274(13) .0160(8) .0094(9) .0160(10) C43A .0322(15) .0361(11) .0264(10) .0148(11) .0094(11) .0169(8) C44A .0315(14) .0232(10) .0266(16) .0081(9) .0027(11) .0131(12) C45A .0187(11) .0329(10) .0310(16) .0087(8) .0020(8) .0145(10) C46A .0207(11) .0252(9) .0232(9) .0072(8) .0042(8) .0104(7) C47A .0374(12) .0423(11) .0421(13) .0085(9) -.0089(9) .0210(10) N5 .0191(6) .0210(6) .0285(6) .0069(4) .0021(4) .0125(5) C5A .0248(7) .0213(7) .0245(7) .0069(5) .0044(5) .0116(6) C6 .0255(8) .0278(8) .0366(8) .0066(6) -.0026(6) .0144(7) C7 .0285(8) .0280(8) .0385(9) .0025(6) -.0057(6) .0128(7) C8 .0371(8) .0227(7) .0282(8) .0044(6) .0015(6) .0090(6) C9 .0322(8) .0245(7) .0245(7) .0117(6) .0056(6) .0112(6) C9A .0239(7) .0238(7) .0206(7) .0083(5) .0047(5) .0117(6) N10 .0224(6) .0241(6) .0286(6) .0078(5) .0026(5) .0113(5) C10A .0191(7) .0247(7) .0251(7) .0074(5) .0058(5) .0134(6) C4B .022(8) .023(8) .040(10) .006(6) .013(6) .022(7) C41B .016(5) .022(6) .019(5) .006(4) .003(3) .010(4) C42B .018(5) .023(6) .016(5) .007(4) .002(3) .012(4) C43B .018(5) .029(6) .016(5) .010(4) .005(4) .009(4) C44B .014(5) .012(6) .014(5) .006(4) -.001(4) .006(4) C45B .020(5) .023(6) .016(5) .006(5) .003(3) .009(4) C46B .020(5) .029(6) .018(5) .007(4) .005(4) .009(4) C47B .036(12) .076(16) .051(15) .022(10) .021(10) .013(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 C2 . 1.3668(17) no N1 C10A . 1.3732(16) no N1 H1 . .8800 no C2 O2 . 1.2176(16) no C2 C3 . 1.5118(17) no C3 C4B . 1.478(13) no C3 C4A . 1.5242(18) no C3 H3A . .9900 no C3 H3B . .9900 no C4A N5 . 1.4752(17) no C4A C41A . 1.512(2) no C4A H4A . 1.0000 no C41A C42A . 1.390(3) no C41A C46A . 1.391(3) no C42A C43A . 1.389(3) no C42A H42A . .9500 no C43A C44A . 1.396(3) no C43A H43A . .9500 no C44A C45A . 1.389(3) no C44A C47A . 1.501(3) no C45A C46A . 1.391(2) no C45A H45A . .9500 no C46A H46A . .9500 no C47A H47A . .9800 no C47A H47B . .9800 no C47A H47C . .9800 no C47A H47D . .9800 no C47A H47E . .9800 no C47A H47F . .9800 no N5 C10A . 1.3653(15) no N5 C5A . 1.4016(17) no N5 C4B . 1.555(12) no C5A C6 . 1.3882(18) no C5A C9A . 1.4080(18) no C6 C7 . 1.384(2) no C6 H6 . .9500 no C7 C8 . 1.395(2) no C7 H7 . .9500 no C8 C9 . 1.3846(19) no C8 H8 . .9500 no C9 C9A . 1.3889(19) no C9 H9 . .9500 no C9A N10 . 1.3948(16) no N10 C10A . 1.3084(17) no C4B C41B . 1.541(18) no C4B H4B . 1.0000 no C41B C42B . 1.32(3) no C41B C46B . 1.39(3) no C42B C43B . 1.41(3) no C42B H42B . .9500 no C43B C44B . 1.35(3) no C43B H43B . .9500 no C44B C45B . 1.23(3) no C44B C47B . 1.58(4) no C45B C46B . 1.34(3) no C45B H45B . .9500 no C46B H46B . .9500 no C47B H47G . .9800 no C47B H47H . .9800 no C47B H47I . .9800 no C47B H47J . .9800 no C47B H47K . .9800 no C47B H47L . .9800 no