data_2011769 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 192 _journal_page_last 194 _publ_section_title ; N,N'-(1,2-phenylene)bis(pyridine-2-carboxamide) and N,N'-(1,2-cyclohexanediyl)bis(pyridine-2-carboxamide) ; loop_ _publ_author_name 'Lin, Jun' 'Zhang, Jun-Yong' 'Xu, Yan' 'Ke, Xiao-Kang' 'Guo, Zijian' _chemical_formula_moiety 'C18 H14 N4 O2' _chemical_formula_sum 'C18 H14 N4 O2' _chemical_formula_weight 318.33 _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 12.346(2) _cell_length_b 5.5670(10) _cell_length_c 22.578(6) _cell_angle_alpha 90 _cell_angle_beta 95.200(10) _cell_angle_gamma 90 _cell_volume 1545.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.368 _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 N1 .1424(2) .9104(5) .41840(10) .0663(7) Uani d . 1 . . N N2 .2666(2) .5723(4) .37461(9) .0519(6) Uani d . 1 . . N H2B .2668 .6217 .4107 .062 Uiso calc R 1 . . H N3 .3395(2) .2482(4) .46983(8) .0475(6) Uani d . 1 . . N H3B .3125 .1202 .4839 .057 Uiso calc R 1 . . H N4 .2551(2) .1948(4) .57402(9) .0573(6) Uani d . 1 . . N O1 .1829(2) .6341(5) .28131(8) .0814(7) Uani d . 1 . . O O2 .3731(2) .6428(4) .49015(7) .0623(6) Uani d . 1 . . O C1 .0860(3) 1.0908(7) .4398(2) .0810(10) Uani d . 1 . . C H1A .0922 1.1138 .4808 .097 Uiso calc R 1 . . H C2 .0195(3) 1.2442(7) .4057(2) .0840(10) Uani d . 1 . . C H2A -.0177 1.3673 .4229 .100 Uiso calc R 1 . . H C3 .0095(3) 1.2105(7) .3454(2) .0870(10) Uani d . 1 . . C H3A -.0347 1.3106 .3207 .104 Uiso calc R 1 . . H C4 .0660(3) 1.0265(6) .32220(10) .0730(10) Uani d . 1 . . C H4A .0598 .9995 .2814 .087 Uiso calc R 1 . . H C5 .1315(2) .8821(5) .35920(10) .0527(7) Uani d . 1 . . C C6 .1961(2) .6858(6) .33440(10) .0545(7) Uani d . 1 . . C C7 .3394(2) .3848(5) .36520(10) .0448(6) Uani d . 1 . . C C8 .3767(2) .3474(6) .30950(10) .0550(7) Uani d . 1 . . C H8A .3565 .4534 .2787 .066 Uiso calc R 1 . . H C9 .4429(2) .1564(6) .29970(10) .0603(8) Uani d . 1 . . C H9A .4654 .1323 .2619 .072 Uiso calc R 1 . . H C10 .4764(2) -.0002(5) .34490(10) .0599(8) Uani d . 1 . . C H10A .5206 -.1305 .3378 .072 Uiso calc R 1 . . H C11 .4431(2) .0398(5) .40100(10) .0511(7) Uani d . 1 . . C H11A .4664 -.0629 .4321 .061 Uiso calc R 1 . . H C12 .3756(2) .2309(5) .41148(9) .0436(6) Uani d . 1 . . C C13 .3435(2) .4438(5) .50480(10) .0453(6) Uani d . 1 . . C C14 .3034(2) .4023(5) .56530(10) .0420(6) Uani d . 1 . . C C15 .3183(2) .5781(5) .60780(10) .0596(8) Uani d . 1 . . C H15A .3527 .7214 .5997 .072 Uiso calc R 1 . . H C16 .2813(3) .5383(6) .66280(10) .0655(9) Uani d . 1 . . C H16A .2915 .6528 .6928 .079 Uiso calc R 1 . . H C17 .2296(2) .3282(6) .67220(10) .0605(8) Uani d . 1 . . C H17A .2024 .2979 .7086 .073 Uiso calc R 1 . . H C18 .2181(3) .1619(6) .62750(10) .0676(9) Uani d . 1 . . C H18A .1828 .0185 .6346 .081 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 .0520(10) .093(2) .0530(10) -.002(2) -.0020(10) -.0130(10) N2 .0550(10) .071(2) .0290(10) -.0060(10) -.0010(10) .0010(10) N3 .0540(10) .0570(10) .0320(10) -.0160(10) .0063(9) .0020(10) N4 .069(2) .060(2) .0460(10) -.0160(10) .0160(10) .0010(10) O1 .089(2) .116(2) .0370(10) .016(2) -.0080(10) -.0020(10) O2 .0870(10) .0620(10) .0370(10) -.0280(10) .0030(9) .0041(9) C1 .055(2) .116(3) .072(2) -.005(2) .000(2) -.030(2) C2 .050(2) .087(3) .113(3) .004(2) .005(2) -.017(2) C3 .069(2) .098(3) .095(3) .010(2) .010(2) .026(2) C4 .064(2) .094(3) .060(2) .007(2) .009(2) .017(2) C5 .0430(10) .068(2) .047(2) -.010(2) .0010(10) .004(2) C6 .054(2) .073(2) .0360(10) -.011(2) .0000(10) .0040(10) C7 .0460(10) .054(2) .0340(10) -.0110(10) .0030(10) -.0010(10) C8 .061(2) .071(2) .0330(10) -.009(2) .0040(10) .004(2) C9 .067(2) .079(2) .0360(10) -.006(2) .0120(10) -.006(2) C10 .064(2) .066(2) .051(2) -.005(2) .0130(10) -.009(2) C11 .055(2) .054(2) .044(2) -.012(2) .0060(10) .0040(10) C12 .0480(10) .055(2) .0290(10) -.0170(10) .0050(10) -.0010(10) C13 .049(2) .052(2) .0340(10) -.0120(10) -.0040(10) .0030(10) C14 .0450(10) .048(2) .0320(10) -.0050(10) .0010(10) .0040(10) C15 .078(2) .058(2) .043(2) -.017(2) .0030(10) -.0040(10) C16 .087(2) .075(2) .035(2) -.001(2) .007(2) -.006(2) C17 .065(2) .081(2) .0380(10) .011(2) .0160(10) .009(2) C18 .079(2) .073(2) .053(2) -.012(2) .023(2) .009(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 N1 C1 . 1.338(4) yes N1 C5 . 1.340(3) yes N2 C6 . 1.356(3) yes N2 C7 . 1.406(3) yes N2 H2B . .8600 ? N3 C13 . 1.343(3) yes N3 C12 . 1.432(3) yes N3 H3B . .8600 ? N4 C14 . 1.324(3) yes N4 C18 . 1.342(3) yes O1 C6 . 1.229(3) yes O2 C13 . 1.222(3) yes C1 C2 . 1.373(5) ? C1 H1A . .9300 ? C2 C3 . 1.368(4) ? C2 H2A . .9300 ? C3 C4 . 1.370(5) ? C3 H3A . .9300 ? C4 C5 . 1.370(4) ? C4 H4A . .9300 ? C5 C6 . 1.491(4) ? C7 C12 . 1.394(3) ? C7 C8 . 1.393(3) ? C8 C9 . 1.372(4) ? C8 H8A . .9300 ? C9 C10 . 1.377(4) ? C9 H9A . .9300 ? C10 C11 . 1.386(4) ? C10 H10A . .9300 ? C11 C12 . 1.384(4) ? C11 H11A . .9300 ? C13 C14 . 1.512(3) ? C14 C15 . 1.371(3) ? C15 C16 . 1.381(4) ? C15 H15A . .9300 ? C16 C17 . 1.358(4) ? C16 H16A . .9300 ? C17 C18 . 1.368(4) ? C17 H17A . .9300 ? C18 H18A . .9300 ?