data_2200305 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2001 _journal_volume 57 _journal_page_first o396 _journal_page_last o398 _publ_section_title ; 9-(4-Methylbenzylidene)-4,8-diphenyl-6-p-tolyl-2-oxa-3,7-diazaspiro[4.4]nona- 3,7-dien-1-one ; loop_ _publ_author_name 'Bruno, Giuseppe' "Nicol\'o, Francesco" 'Rotondo, Archimede' 'Foti, Francesco' 'Risitano, Francesco' 'Grassi, Giovanni' 'Bilardo, Cristina' _chemical_formula_moiety 'C33 H26 N2 O2' _chemical_formula_sum 'C33 H26 N2 O2' _chemical_formula_iupac 'C33 H26 N2 O2' _chemical_formula_weight 482.56 _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 10.909(3) _cell_length_b 18.502(7) _cell_length_c 13.092(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.143(12) _cell_angle_gamma 90.00 _cell_volume 2621.9(15) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _exptl_crystal_density_diffrn 1.222 _diffrn_ambient_temperature 298(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 C3 .8696(4) .23869(19) .2732(3) .0657(10) Uani d . 1 . . C O2 .9447(2) .20392(13) .23488(18) .0828(8) Uani d . 1 . . O C1 .8783(3) .27669(17) .3770(2) .0542(8) Uani d . 1 . . C C2 .7621(3) .31989(18) .3618(2) .0568(9) Uani d . 1 . . C N1 .6886(3) .30278(16) .2801(2) .0752(9) Uani d . 1 . . N O1 .7530(2) .25016(13) .22350(17) .0810(8) Uani d . 1 . . O C14 .7272(3) .38018(18) .4265(3) .0585(9) Uani d . 1 . . C C15 .6598(3) .4372(2) .3791(3) .0773(11) Uani d . 1 . . C H15 .6331 .4353 .3089 .093 Uiso calc R 1 . . H C16 .6323(4) .4968(2) .4353(4) .0946(14) Uani d . 1 . . C H16 .5887 .5352 .4025 .113 Uiso calc R 1 . . H C17 .6688(4) .4997(2) .5397(4) .0980(14) Uani d . 1 . . C H17 .6487 .5397 .5774 .118 Uiso calc R 1 . . H C18 .7351(4) .4437(2) .5881(3) .0891(12) Uani d . 1 . . C H18 .7592 .4455 .6587 .107 Uiso calc R 1 . . H C19 .7664(3) .38412(19) .5317(3) .0732(11) Uani d . 1 . . C H19 .8135 .3469 .5643 .088 Uiso calc R 1 . . H C4 .8801(3) .21671(17) .4665(2) .0591(9) Uani d . 1 . . C H4 .8351 .2367 .5203 .071 Uiso calc R 1 . . H N2 1.0105(3) .20973(15) .5103(2) .0646(8) Uani d . 1 . . N C5 1.0739(3) .26304(19) .4793(2) .0587(9) Uani d . 1 . . C C6 1.0018(3) .31331(19) .4075(2) .0563(9) Uani d . 1 . . C C7 .8206(3) .14485(19) .4336(2) .0609(9) Uani d . 1 . . C C8 .8888(3) .0855(2) .4104(2) .0710(10) Uani d . 1 . . C H8 .9743 .0889 .4148 .085 Uiso calc R 1 . . H C9 .8309(4) .0207(2) .3805(3) .0811(12) Uani d . 1 . . C H9 .8786 -.0186 .3653 .097 Uiso calc R 1 . . H C10 .7049(5) .0133(3) .3730(3) .0932(14) Uani d . 1 . . C C11 .6373(4) .0725(3) .3966(3) .1070(16) Uani d . 1 . . C H11 .5518 .0687 .3922 .128 Uiso calc R 1 . . H C12 .6935(4) .1377(2) .4267(3) .0927(13) Uani d . 1 . . C H12 .6455 .1768 .4424 .111 Uiso calc R 1 . . H C13 .6431(4) -.0589(2) .3402(3) .143(2) Uani d . 1 . . C H13A .5552 -.0542 .3379 .171 Uiso calc R 1 . . H H13B .6724 -.0957 .3890 .171 Uiso calc R 1 . . H H13C .6631 -.0719 .2733 .171 Uiso calc R 1 . . H C20 1.2067(3) .27094(17) .5154(3) .0611(9) Uani d . 1 . . C C21 1.2897(3) .29086(18) .4488(3) .0756(11) Uani d . 1 . . C H21 1.2612 .3009 .3804 .091 Uiso calc R 1 . . H C22 1.4142(4) .2960(2) .4825(4) .0928(13) Uani d . 1 . . C H22 1.4693 .3082 .4365 .111 Uiso calc R 1 . . H C23 1.4565(4) .2833(2) .5838(4) .1046(16) Uani d . 1 . . C H23 1.5404 .2877 .6067 .125 Uiso calc R 1 . . H C24 1.3756(4) .2639(2) .6521(4) .1035(15) Uani d . 1 . . C H24 1.4048 .2551 .7208 .124 Uiso calc R 1 . . H C25 1.2506(4) .25749(19) .6180(3) .0821(12) Uani d . 1 . . C H25 1.1959 .2442 .6638 .099 Uiso calc R 1 . . H C26 1.0358(3) .38088(18) .3855(2) .0609(9) Uani d . 1 . . C H26 1.1133 .3954 .4164 .073 Uiso calc R 1 . . H C27 .9665(3) .43470(19) .3192(3) .0589(9) Uani d . 1 . . C C28 .9031(3) .41793(18) .2233(3) .0675(10) Uani d . 1 . . C H28 .9081 .3714 .1974 .081 Uiso calc R 1 . . H C29 .8324(3) .4695(2) .1655(3) .0721(11) Uani d . 1 . . C H29 .7890 .4567 .1024 .087 Uiso calc R 1 . . H C30 .8260(3) .5397(2) .2010(3) .0688(10) Uani d . 1 . . C C31 .8929(3) .55711(19) .2943(3) .0741(11) Uani d . 1 . . C H31 .8911 .6043 .3186 .089 Uiso calc R 1 . . H C32 .9623(3) .50596(19) .3519(3) .0676(10) Uani d . 1 . . C H32 1.0073 .5194 .4140 .081 Uiso calc R 1 . . H C33 .7501(4) .5968(2) .1383(3) .1054(14) Uani d . 1 . . C H33A .7104 .5755 .0759 .127 Uiso calc R 1 . . H H33B .8033 .6352 .1217 .127 Uiso calc R 1 . . H H33C .6887 .6156 .1776 .127 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 C3 .072(3) .063(3) .060(2) -.005(2) .001(2) .005(2) O2 .097(2) .0794(18) .0742(17) -.0003(16) .0208(16) -.0103(14) C1 .050(2) .063(2) .0482(19) -.0031(19) -.0004(16) -.0003(17) C2 .050(2) .063(2) .056(2) -.0063(19) -.0007(18) .0039(19) N1 .064(2) .085(2) .072(2) -.0039(18) -.0083(17) -.0061(18) O1 .0822(19) .0867(18) .0686(16) -.0029(16) -.0127(14) -.0155(14) C14 .045(2) .066(2) .064(2) -.0017(19) .0048(18) .004(2) C15 .067(3) .083(3) .084(3) .013(2) .019(2) .008(2) C16 .072(3) .090(4) .125(4) .020(3) .028(3) .015(3) C17 .077(3) .078(3) .144(5) .007(3) .034(3) -.018(3) C18 .083(3) .094(3) .093(3) -.008(3) .020(3) -.027(3) C19 .072(3) .072(3) .074(3) -.001(2) .002(2) -.007(2) C4 .058(2) .062(2) .057(2) -.001(2) .0095(18) .0007(18) N2 .060(2) .0633(19) .0672(18) -.0036(17) -.0049(15) .0037(15) C5 .059(2) .060(2) .056(2) .005(2) .0009(18) -.0042(18) C6 .054(2) .062(2) .052(2) .000(2) .0038(17) .0001(18) C7 .057(2) .058(2) .066(2) -.005(2) .0022(19) .0050(19) C8 .075(3) .069(3) .071(2) -.006(2) .019(2) -.005(2) C9 .107(4) .066(3) .072(3) -.008(3) .018(3) -.011(2) C10 .106(4) .084(3) .082(3) -.027(3) -.015(3) .004(3) C11 .066(3) .100(4) .148(4) -.025(3) -.016(3) .020(3) C12 .071(3) .073(3) .131(4) -.002(3) .000(3) .015(3) C13 .189(5) .108(4) .119(4) -.068(4) -.035(3) .000(3) C20 .056(2) .056(2) .067(2) .0028(19) -.008(2) -.0018(19) C21 .059(3) .078(3) .086(3) .002(2) -.003(2) -.001(2) C22 .062(3) .095(3) .119(4) .003(3) .002(3) .007(3) C23 .058(3) .097(3) .149(5) .003(3) -.025(3) -.002(3) C24 .082(3) .111(4) .107(4) .000(3) -.029(3) .010(3) C25 .071(3) .092(3) .078(3) .000(2) -.013(2) .008(2) C26 .054(2) .068(2) .060(2) -.004(2) .0043(18) .0003(19) C27 .056(2) .064(2) .057(2) -.005(2) .0061(18) .0035(19) C28 .080(3) .059(2) .064(2) -.004(2) .012(2) .003(2) C29 .079(3) .079(3) .058(2) -.003(2) .006(2) .004(2) C30 .069(3) .067(3) .071(3) .003(2) .011(2) .016(2) C31 .085(3) .059(2) .080(3) -.002(2) .015(2) .005(2) C32 .076(3) .063(2) .065(2) -.012(2) .012(2) .002(2) C33 .107(3) .099(3) .110(3) .023(3) .011(3) .030(3) 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 C3 O2 . 1.199(4) yes C3 O1 . 1.372(4) yes C3 C1 . 1.522(4) yes C1 C2 . 1.490(4) yes C1 C6 . 1.517(4) yes C1 C4 . 1.612(4) yes C2 N1 . 1.293(3) yes C2 C14 . 1.479(4) yes N1 O1 . 1.456(3) yes C14 C15 . 1.388(4) ? C14 C19 . 1.392(4) ? C15 C16 . 1.378(5) ? C16 C17 . 1.376(5) ? C17 C18 . 1.373(5) ? C18 C19 . 1.393(4) ? C4 N2 . 1.471(4) yes C4 C7 . 1.518(4) ? N2 C5 . 1.298(4) yes C5 C20 . 1.475(4) ? C5 C6 . 1.477(4) yes C6 C26 . 1.345(4) yes C7 C8 . 1.382(4) ? C7 C12 . 1.384(4) ? C8 C9 . 1.388(4) ? C9 C10 . 1.373(5) ? C10 C11 . 1.377(5) ? C10 C13 . 1.532(5) ? C11 C12 . 1.389(5) ? C20 C21 . 1.382(4) ? C20 C25 . 1.392(4) ? C21 C22 . 1.378(5) ? C22 C23 . 1.369(5) ? C23 C24 . 1.381(5) ? C24 C25 . 1.386(5) ? C26 C27 . 1.468(4) yes C27 C32 . 1.389(4) ? C27 C28 . 1.390(4) ? C28 C29 . 1.390(4) ? C29 C30 . 1.384(4) ? C30 C31 . 1.381(4) ? C30 C33 . 1.517(4) ? C31 C32 . 1.377(4) ?