data_2011890 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 489 _journal_page_last 490 _publ_section_title ; Bis[4-(2-pyridylmethyleneamino)phenyl] ether ; loop_ _publ_author_name 'Ana Tesouro Vallina' 'Helen Stoeckli-Evans' _chemical_formula_moiety 'C24 H18 N4 O' _chemical_formula_sum 'C24 H18 N4 O' _chemical_formula_weight 378.42 _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 12.3403(8) _cell_length_b 18.3849(17) _cell_length_c 8.5868(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.958(8) _cell_angle_gamma 90.00 _cell_volume 1947.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _exptl_crystal_density_diffrn 1.291 _diffrn_ambient_temperature 153(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 N1 .19492(9) .18318(8) -.25245(15) .0586(3) Uani d . 1 . . N N2 .42393(7) .11855(5) -.03145(11) .0353(2) Uani d . 1 . . N N3 .89625(8) -.04533(6) .85138(13) .0444(3) Uani d . 1 . . N N4 1.15560(9) -.12726(7) .83900(13) .0531(3) Uani d . 1 . . N O1 .62405(7) .15817(4) .55555(10) .0415(2) Uani d . 1 . . O C1 .15263(14) .18432(10) -.3984(2) .0676(5) Uani d . 1 . . C H1 .0842(16) .2090(11) -.410(2) .094(6) Uiso d . 1 . . H C2 .20045(13) .15302(9) -.52382(18) .0585(4) Uani d . 1 . . C H2 .1649(13) .1581(9) -.625(2) .070(5) Uiso d . 1 . . H C3 .29796(12) .11791(8) -.49962(17) .0509(3) Uani d . 1 . . C H3 .3340(14) .0957(9) -.590(2) .072(5) Uiso d . 1 . . H C4 .34383(10) .11572(7) -.35085(15) .0416(3) Uani d . 1 . . C H4 .4160(13) .0922(8) -.3283(18) .060(4) Uiso d . 1 . . H C5 .28982(9) .14844(6) -.23027(14) .0383(3) Uani d . 1 . . C C6 .33588(10) .15064(7) -.06976(15) .0388(3) Uani d . 1 . . C H6 .2944(11) .1796(8) .0061(18) .052(4) Uiso d . 1 . . H C7 .47095(8) .12860(6) .11985(13) .0326(2) Uani d . 1 . . C C8 .47424(9) .19635(6) .19436(14) .0347(3) Uani d . 1 . . C H8 .4408(10) .2389(8) .1432(16) .047(4) Uiso d . 1 . . H C9 .52812(9) .20472(6) .33687(14) .0348(3) Uani d . 1 . . C H9 .5329(10) .2512(7) .3860(15) .040(3) Uiso d . 1 . . H C10 .57698(9) .14531(6) .40985(13) .0334(3) Uani d . 1 . . C C11 .57441(10) .07771(6) .33773(15) .0385(3) Uani d . 1 . . C H11 .6093(10) .0376(7) .3857(16) .042(3) Uiso d . 1 . . H C12 .52391(9) .07033(6) .19232(15) .0370(3) Uani d . 1 . . C H12 .5232(10) .0246(8) .1399(16) .045(4) Uiso d . 1 . . H C13 .69384(9) .10627(6) .62260(14) .0360(3) Uani d . 1 . . C C14 .66890(10) .07921(7) .76643(15) .0387(3) Uani d . 1 . . C H14 .6027(12) .0929(7) .8145(17) .048(4) Uiso d . 1 . . H C15 .73845(9) .02957(7) .83957(15) .0387(3) Uani d . 1 . . C H15 .7213(10) .0097(7) .9386(17) .045(4) Uiso d . 1 . . H C16 .83293(9) .00778(7) .77040(14) .0389(3) Uani d . 1 . . C C17 .85625(11) .03622(8) .62480(16) .0476(3) Uani d . 1 . . C H17 .9225(12) .0224(8) .5713(19) .060(4) Uiso d . 1 . . H C18 .78724(11) .08536(8) .55046(16) .0456(3) Uani d . 1 . . C H18 .8029(12) .1044(8) .449(2) .061(4) Uiso d . 1 . . H C19 .99335(11) -.05683(8) .81938(16) .0475(3) Uani d . 1 . . C H19 1.0315(14) -.0257(10) .740(2) .081(5) Uiso d . 1 . . H C20 1.05838(9) -.11380(7) .89892(15) .0414(3) Uani d . 1 . . C C21 1.02147(11) -.15013(8) 1.02727(18) .0514(3) Uani d . 1 . . C H21 .9473(13) -.1382(9) 1.0666(19) .067(5) Uiso d . 1 . . H C22 1.08610(12) -.20248(8) 1.0971(2) .0576(4) Uani d . 1 . . C H22 1.0636(14) -.2306(10) 1.180(2) .076(5) Uiso d . 1 . . H C23 1.18595(11) -.21664(8) 1.03724(18) .0515(3) Uani d . 1 . . C H23 1.2346(12) -.2519(9) 1.0876(19) .061(4) Uiso d . 1 . . H C24 1.21686(11) -.17804(8) .90864(17) .0519(4) Uani d . 1 . . C H24 1.2860(13) -.1873(8) .8612(18) .062(4) 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 N1 .0478(6) .0782(9) .0491(8) .0168(6) -.0072(5) -.0018(6) N2 .0390(5) .0333(5) .0335(6) -.0007(4) -.0015(4) .0010(4) N3 .0428(6) .0512(6) .0390(6) .0065(5) -.0031(4) .0056(5) N4 .0460(6) .0752(8) .0381(7) .0124(6) .0015(5) .0025(6) O1 .0518(5) .0380(4) .0339(5) .0091(4) -.0092(4) -.0047(3) C1 .0585(9) .0865(12) .0565(11) .0204(8) -.0176(8) .0026(8) C2 .0673(9) .0655(9) .0414(9) -.0043(7) -.0161(7) .0052(7) C3 .0579(8) .0541(8) .0403(8) -.0079(6) -.0028(6) -.0046(6) C4 .0437(7) .0401(6) .0406(8) -.0033(5) -.0029(5) -.0025(5) C5 .0376(6) .0380(6) .0391(7) -.0020(5) -.0022(5) .0041(5) C6 .0387(6) .0423(6) .0355(7) .0015(5) .0024(5) .0006(5) C7 .0332(5) .0347(6) .0300(6) -.0003(4) .0019(4) .0008(5) C8 .0389(6) .0328(6) .0326(7) .0055(5) .0029(5) .0027(5) C9 .0421(6) .0295(6) .0330(7) .0035(4) .0033(5) -.0033(5) C10 .0350(6) .0358(6) .0293(6) .0011(4) -.0005(4) -.0008(4) C11 .0451(6) .0293(6) .0405(7) .0045(5) -.0071(5) .0017(5) C12 .0438(6) .0291(6) .0379(7) .0018(5) -.0033(5) -.0037(5) C13 .0403(6) .0347(6) .0325(7) .0009(5) -.0072(5) -.0027(5) C14 .0366(6) .0422(6) .0371(7) -.0004(5) .0003(5) -.0021(5) C15 .0405(6) .0435(6) .0319(7) -.0029(5) -.0006(5) .0033(5) C16 .0396(6) .0422(6) .0345(7) .0011(5) -.0056(5) .0012(5) C17 .0436(7) .0613(8) .0382(8) .0110(6) .0046(5) .0051(6) C18 .0501(7) .0542(8) .0325(7) .0072(6) .0028(5) .0065(6) C19 .0449(7) .0593(8) .0381(8) .0040(6) -.0030(5) .0064(6) C20 .0390(6) .0496(7) .0350(7) .0025(5) -.0057(5) -.0018(5) C21 .0406(7) .0599(8) .0537(9) .0028(6) .0018(6) .0090(7) C22 .0547(8) .0578(9) .0602(10) .0007(7) .0004(7) .0192(7) C23 .0512(8) .0462(7) .0562(9) .0082(6) -.0107(6) -.0022(6) C24 .0446(7) .0685(9) .0422(8) .0148(6) -.0033(6) -.0093(7) 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 C1 . 1.341(2) ? N1 C5 . 1.3418(16) ? N2 C6 . 1.2698(15) ? N2 C7 . 1.4167(15) ? N3 C19 . 1.2564(17) ? N3 C16 . 1.4179(15) ? N4 C24 . 1.3302(18) ? N4 C20 . 1.3445(16) ? O1 C10 . 1.3817(14) ? O1 C13 . 1.3963(13) ? C1 C2 . 1.372(2) ? C1 H1 . .96(2) ? C2 C3 . 1.375(2) ? C2 H2 . .965(17) ? C3 C4 . 1.3800(19) ? C3 H3 . .995(18) ? C4 C5 . 1.3874(18) ? C4 H4 . 1.003(16) ? C5 C6 . 1.4734(17) ? C6 H6 . .996(15) ? C7 C12 . 1.3908(16) ? C7 C8 . 1.4002(16) ? C8 C9 . 1.3811(17) ? C8 H8 . .981(14) ? C9 C10 . 1.3869(16) ? C9 H9 . .954(13) ? C10 C11 . 1.3885(16) ? C11 C12 . 1.3830(17) ? C11 H11 . .941(14) ? C12 H12 . .953(14) ? C13 C14 . 1.3760(18) ? C13 C18 . 1.3816(18) ? C14 C15 . 1.3882(17) ? C14 H14 . .961(15) ? C15 C16 . 1.3857(17) ? C15 H15 . .955(15) ? C16 C17 . 1.3943(19) ? C17 C18 . 1.3827(18) ? C17 H17 . .984(16) ? C18 H18 . .966(17) ? C19 C20 . 1.4731(18) ? C19 H19 . 1.02(2) ? C20 C21 . 1.3793(19) ? C21 C22 . 1.375(2) ? C21 H21 . 1.010(16) ? C22 C23 . 1.376(2) ? C22 H22 . .932(19) ? C23 C24 . 1.377(2) ? C23 H23 . .974(16) ? C24 H24 . .973(16) ?