data_2007367 _journal_name_full 'Acta Crystallographica' _journal_year 1998 _journal_volume C54 _journal_page_first 785 _journal_page_last 787 _publ_section_title ; 2-(1-Methyl-1,2-dihydro-2- pyridylideneaminomethylene)propanedinitrile ; loop_ _publ_author_name "J\'an Lokaj" 'Viktor Kettmann' 'Viktor Milata' 'Rudolf Kada' 'Jordis Ulrich' _chemical_formula_moiety 'C10 H8 N4 ' _chemical_formula_sum 'C10 H8 N4 ' _chemical_formula_weight 184.20 _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.686(8) _cell_length_b 3.956(2) _cell_length_c 20.404(13) _cell_angle_alpha 90.00 _cell_angle_beta 106.06(7) _cell_angle_gamma 90.00 _cell_volume 906.5(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_meas 1.350(10) _diffrn_ambient_temperature 293(2) _refine_ls_R_factor_obs .0502 _refine_ls_wR_factor_obs .0975 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol N1 .46970(15) .1559(5) .62940(9) .0379(5) Uani d . 1 . N C2 .3602(2) .0113(6) .60800(10) .0366(6) Uani d . 1 . C C3 .3144(2) -.1333(7) .65795(11) .0463(7) Uani d . 1 . C C4 .3786(2) -.1350(8) .72425(12) .0535(7) Uani d . 1 . C C5 .4911(2) .0082(8) .74341(11) .0553(7) Uani d . 1 . C C6 .5334(2) .1518(7) .69586(12) .0492(7) Uani d . 1 . C N7 .3102(2) .0300(5) .54024(9) .0400(5) Uani d . 1 . N C8 .2041(2) -.1056(6) .51493(11) .0402(6) Uani d . 1 . C C9 .1468(2) -.0957(6) .44643(11) .0390(6) Uani d . 1 . C C10 .0330(2) -.2424(7) .42105(11) .0426(6) Uani d . 1 . C N11 -.0585(2) -.3587(7) .39961(11) .0606(7) Uani d . 1 . N C12 .1973(2) .0581(7) .39846(12) .0432(6) Uani d . 1 . C N13 .2354(2) .1785(7) .35845(11) .0606(7) Uani d . 1 . N C14 .5203(2) .3233(7) .57948(12) .0489(7) Uani d . 1 . C H3 .2368 -.2369 .6449 .056 Uiso d . 1 . H H4 .3451 -.2490 .7606 .065 Uiso d . 1 . H H5 .5338 .0070 .7910 .068 Uiso d . 1 . H H6 .6056 .2558 .7046 .060 Uiso d . 1 . H H8 .1558 -.2299 .5431 .048 Uiso d . 1 . H H141 .5430 .1568 .5507 .058 Uiso d . 1 . H H142 .4500 .4836 .5489 .058 Uiso d . 1 . H H143 .5965 .4461 .6048 .058 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 .0343(10) .0433(13) .0337(10) -.0029(10) .0053(8) -.0019(9) C2 .0291(12) .0420(15) .0344(12) -.0009(12) .0018(9) -.0016(11) C3 .0396(13) .058(2) .0393(13) -.0079(13) .0078(10) .0020(13) C4 .0525(15) .068(2) .0370(13) -.0083(15) .0063(11) .0034(14) C5 .055(2) .071(2) .0326(12) -.007(2) -.0006(12) .0010(14) C6 .0387(13) .057(2) .0448(14) -.0072(13) -.0001(11) -.0059(14) N7 .0333(10) .0499(13) .0338(10) -.0013(10) .0041(8) -.0004(9) C8 .0366(12) .046(2) .0370(12) -.0005(12) .0082(10) -.0012(12) C9 .0324(12) .049(2) .0349(12) -.0030(12) .0076(10) -.0024(12) C10 .0398(14) .055(2) .0320(11) .0012(14) .0080(11) -.0019(13) N11 .0432(12) .087(2) .0476(12) -.0193(13) .0053(10) -.0031(13) C12 .0326(12) .051(2) .0397(13) .0028(12) -.0010(11) .0001(13) N13 .0463(13) .084(2) .0483(12) -.0098(13) .0085(11) .0107(13) C14 .0404(13) .058(2) .0499(14) -.0077(13) .0141(12) .0005(13) 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 C6 . 1.354(3) yes N1 C2 . 1.359(3) yes N1 C14 . 1.469(3) yes C2 N7 . 1.346(3) yes C2 C3 . 1.398(3) yes C3 C4 . 1.354(3) yes C4 C5 . 1.384(4) yes C5 C6 . 1.332(3) yes N7 C8 . 1.318(3) yes C8 C9 . 1.373(3) yes C9 C10 . 1.411(3) yes C9 C12 . 1.412(3) yes C10 N11 . 1.135(3) yes C12 N13 . 1.137(3) yes