data_2200131 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2001 _journal_volume 57 _journal_page_first o236 _journal_page_last o238 _publ_section_title ; 2,2'-{2-[(E)-3-phenylprop-2-enyl]-2,3-dihydro-1H-isoindol-1,3-diylidene}- dimalononitrile, a \p-deficient system for \p...\p (1:1) stacking investigations ; loop_ _publ_author_name 'Crean, Colm' 'Gallagher, John F.' 'Pratt, Albert C.' _chemical_name_common "2,2'-(Cinnamylisoindolin-1,3-diylidene)bispropanedinitrile" _chemical_formula_moiety 'C23 H13 N5' _chemical_formula_sum 'C23 H13 N5' _chemical_formula_structural 'C23 H13 N5' _chemical_formula_iupac 'C23 H13 N5' _chemical_formula_weight 359.38 _chemical_melting_point 470 _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 14.3872(18) _cell_length_b 8.2696(10) _cell_length_c 16.1442(15) _cell_angle_alpha 90 _cell_angle_beta 108.327(7) _cell_angle_gamma 90 _cell_volume 1823.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296.0(10) _exptl_crystal_density_diffrn 1.309 _diffrn_ambient_temperature 296.0(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 -.00647(8) .87131(15) .15563(8) .0367(3) Uani d . 1 . . N N2A -.11664(14) 1.4060(2) .04262(12) .0788(6) Uani d . 1 . . N N3A -.24231(13) 1.0780(3) .17486(15) .0907(6) Uani d . 1 . . N N2B .28853(13) .5619(2) .18438(12) .0732(5) Uani d . 1 . . N N3B .04444(12) .42660(19) .24932(11) .0620(4) Uani d . 1 . . N C1 -.07949(11) .7765(2) .18104(10) .0437(4) Uani d . 1 . . C C2 -.05987(12) .7661(2) .27751(11) .0470(4) Uani d . 1 . . C C3 .00903(12) .8440(2) .33779(11) .0458(4) Uani d . 1 . . C C4 -.01804(11) 1.02862(18) .12450(9) .0380(3) Uani d . 1 . . C C5 .08302(10) .80880(18) .15561(9) .0349(3) Uani d . 1 . . C C11 .06880(11) 1.06855(18) .10020(9) .0380(3) Uani d . 1 . . C C12 .09685(13) 1.2087(2) .06691(10) .0479(4) Uani d . 1 . . C C13 .18639(13) 1.2119(2) .05246(11) .0539(5) Uani d . 1 . . C C14 .24716(13) 1.0783(2) .07089(11) .0524(4) Uani d . 1 . . C C15 .22077(11) .9379(2) .10446(10) .0443(4) Uani d . 1 . . C C16 .13076(10) .93386(18) .11947(9) .0363(3) Uani d . 1 . . C C6A -.09671(11) 1.1275(2) .11819(10) .0465(4) Uani d . 1 . . C C7A -.10479(13) 1.2830(2) .07685(12) .0559(5) Uani d . 1 . . C C8A -.17655(13) 1.0939(2) .14997(13) .0598(5) Uani d . 1 . . C C6B .11864(11) .65823(18) .18467(9) .0390(4) Uani d . 1 . . C C7B .21323(13) .6091(2) .18276(11) .0483(4) Uani d . 1 . . C C8B .07334(12) .5348(2) .22056(10) .0441(4) Uani d . 1 . . C C21 .03457(13) .8243(2) .43290(11) .0488(4) Uani d . 1 . . C C22 -.01487(18) .7189(2) .47126(13) .0697(6) Uani d . 1 . . C C23 .0135(2) .6989(3) .56013(15) .0909(8) Uani d . 1 . . C C24 .0913(2) .7812(3) .61307(15) .0896(8) Uani d . 1 . . C C25 .14131(17) .8881(3) .57716(14) .0791(7) Uani d . 1 . . C C26 .11258(13) .9101(3) .48711(12) .0601(5) Uani d . 1 . . C H1A -.0814 .6679 .1578 .052 Uiso calc R 1 . . H H1B -.1435 .8246 .1547 .052 Uiso calc R 1 . . H H2 -.1002 .6980 .2969 .056 Uiso calc R 1 . . H H3 .0453 .9194 .3181 .055 Uiso calc R 1 . . H H12 .0560 1.2987 .0546 .057 Uiso calc R 1 . . H H13 .2060 1.3048 .0301 .065 Uiso calc R 1 . . H H14 .3071 1.0829 .0605 .063 Uiso calc R 1 . . H H15 .2621 .8486 .1167 .053 Uiso calc R 1 . . H H22 -.0681 .6608 .4362 .084 Uiso calc R 1 . . H H23 -.0210 .6282 .5844 .109 Uiso calc R 1 . . H H24 .1107 .7655 .6731 .108 Uiso calc R 1 . . H H25 .1943 .9455 .6131 .095 Uiso calc R 1 . . H H26 .1462 .9831 .4632 .072 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 .0329(6) .0395(7) .0373(6) .0023(5) .0102(5) .0005(5) N2A .0846(13) .0526(10) .0805(12) .0195(9) -.0009(10) .0042(9) N3A .0570(11) .1029(16) .1203(17) .0166(11) .0396(11) -.0124(13) N2B .0652(11) .0815(12) .0802(12) .0323(10) .0333(9) .0223(10) N3B .0682(10) .0506(9) .0639(10) -.0038(8) .0162(8) .0115(8) C1 .0340(8) .0465(9) .0508(9) -.0028(7) .0133(7) -.0014(7) C2 .0429(9) .0499(10) .0543(10) -.0040(8) .0241(8) .0002(8) C3 .0461(9) .0452(9) .0516(9) -.0007(7) .0232(8) -.0014(8) C4 .0376(8) .0377(8) .0331(7) .0013(6) .0030(6) -.0037(6) C5 .0330(7) .0390(8) .0302(7) .0013(6) .0063(6) -.0030(6) C11 .0375(8) .0391(8) .0325(7) -.0016(6) .0042(6) -.0024(6) C12 .0539(10) .0373(9) .0462(9) -.0018(7) .0070(7) .0019(7) C13 .0580(11) .0481(10) .0537(10) -.0152(9) .0148(8) .0051(8) C14 .0446(9) .0603(11) .0528(10) -.0107(8) .0160(8) .0012(8) C15 .0381(8) .0501(9) .0439(8) -.0003(7) .0116(7) .0009(7) C16 .0351(7) .0397(8) .0305(7) -.0014(6) .0051(6) -.0015(6) C6A .0405(8) .0460(9) .0460(9) .0071(7) .0035(7) -.0070(7) C7A .0512(10) .0479(11) .0550(10) .0125(8) -.0028(8) -.0075(9) C8A .0430(10) .0642(12) .0672(12) .0152(9) .0102(9) -.0109(9) C6B .0393(8) .0404(8) .0358(7) .0043(7) .0097(6) .0017(6) C7B .0517(10) .0477(9) .0469(9) .0126(8) .0173(8) .0090(8) C8B .0469(9) .0416(9) .0400(8) .0052(7) .0080(7) .0020(7) C21 .0536(10) .0469(9) .0495(9) .0109(8) .0212(8) -.0031(8) C22 .0976(16) .0588(12) .0567(11) -.0052(11) .0299(11) .0051(9) C23 .148(2) .0689(15) .0624(14) -.0006(16) .0430(16) .0082(12) C24 .137(2) .0792(16) .0507(12) .0340(17) .0264(14) .0085(12) C25 .0769(14) .0912(17) .0586(12) .0252(13) .0061(11) -.0192(12) C26 .0550(11) .0695(13) .0572(11) .0104(10) .0197(9) -.0117(9) 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 . 1.469(2) yes N1 C4 . 1.386(2) yes N1 C5 . 1.388(2) yes N2A C7A . 1.145(2) yes N3A C8A . 1.146(2) yes N2B C7B . 1.144(2) yes N3B C8B . 1.145(2) yes C1 C2 . 1.495(2) yes C2 C3 . 1.319(2) yes C3 C21 . 1.471(2) yes C4 C6A . 1.374(2) yes C4 C11 . 1.460(2) yes C5 C6B . 1.372(2) yes C5 C16 . 1.461(2) yes C11 C12 . 1.389(2) no C11 C16 . 1.399(2) no C12 C13 . 1.380(2) no C13 C14 . 1.382(3) no C14 C15 . 1.384(2) no C15 C16 . 1.391(2) no C6A C8A . 1.425(3) no C6A C7A . 1.436(3) no C6B C8B . 1.428(2) no C6B C7B . 1.430(2) no C21 C26 . 1.382(3) no C21 C22 . 1.388(3) no C22 C23 . 1.373(3) no C23 C24 . 1.359(4) no C24 C25 . 1.377(4) no C25 C26 . 1.393(3) no