data_2006442 _journal_name_full 'Acta Crystallographica' _journal_year 1997 _journal_volume C53 _journal_page_first 1301 _journal_page_last 1302 _publ_section_title ; The 4:2 Diels--Alder Adduct of 1,3-Cyclopentadiene with 1,4-Naphthoquinone ; loop_ _publ_author_name 'G\"une\;s, Bilal' 'Soylu, H\"useyin' '\"Ozbey, S\"uheyla' 'Kendi, Engin' 'Ayd\?in, Ali' _chemical_formula_sum 'C15 H12 O2' _chemical_formula_weight 224.25 _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4077(12) _cell_length_b 10.1752(10) _cell_length_c 12.5542(13) _cell_angle_alpha 71.698(9) _cell_angle_beta 86.980(9) _cell_angle_gamma 77.019(10) _cell_volume 1111.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.340 _diffrn_ambient_temperature 293(2) _refine_ls_R_factor_obs .0624 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 O1 .1014(2) .6332(3) .7649(2) .0790(7) Uani d . 1 . O O2 .1089(3) .9590(3) .3339(2) 0..0770(7) Uani d . 1 . O C1 .1062(3) .7083(3) .6684(2) .0511(7) Uani d . 1 . C C2 .0091(3) .7011(3) .5806(2) .0438(6) Uani d . 1 . C C3 .0113(3) .7858(3) .4692(2) .0440(6) Uani d . 1 . C C4 .1112(3) .8834(3) .4313(2) .0495(7) Uani d . 1 . C C5 .2167(3) .8932(3) .5129(2) .0490(7) Uani d . 1 . C C6 .2092(3) .8063(3) .6376(2) .0487(7) Uani d . 1 . C C7 -.0874(3) .6113(4) .6127(3) .0602(8) Uani d . 1 . C C8 -.1828(4) .6073(4) .5342(3) .0710(10) Uani d . 1 . C C9 -.1834(4) .6931(4) .4248(3) .0690(10) Uani d . 1 . C C10 -.0878(3) .7803(4) .3919(3) .0567(8) Uani d . 1 . C C11 .3798(3) .8407(3) .4843(3) .0531(7) Uani d . 1 . C C12 .4016(3) .6870(3) .4953(3) .0543(8) Uani d . 1 . C C13 .3972(3) .6168(4) .6030(3) .0575(8) Uani d . 1 . C C14 .3713(3) .7241(3) .6658(3) .0546(8) Uani d . 1 . C C15 .4523(4) .8325(4) .5931(3) .0653(9) Uani d . 1 . C O1A .5377(3) .7182(3) 1.2384(2) .0880(8) Uani d . 1 . O O2A .3183(3) .9822(3) .8202(2) .0797(7) Uani d . 1 . O C1A .4826(3) .7672(3) 1.1446(2) .0520(7) Uani d . 1 . C C2A .5743(3) .7679(3) 1.0449(2) .0466(7) Uani d . 1 . C C3A .5186(3) .8417(3) .9359(2) .0462(6) Uani d . 1 . C C4A .3629(3) .9145(3) .9159(2) .0496(7) Uani d . 1 . C C5A .2597(3) .9012(3) 1.0106(2) .0497(7) Uani d . 1 . C C6A .3221(3) .8265(3) 1.1309(2) .0498(7) Uani d . 1 . C C7A .7197(4) .6936(4) 1.0596(3) .0656(9) Uani d . 1 . C C8A .8074(4) .6959(4) .9694(4) .0760(10) Uani d . 1 . C C9A .7551(4) .7733(5) .8619(4) .0780(10) Uani d . 1 . C C10A .6122(4) .8452(4) .8458(3) .0632(9) Uani d . 1 . C C11A .1459(4) .8133(4) 1.0029(3) .0634(9) Uani d . 1 . C C12A .2296(4) .6686(4) 1.0076(3) .0680(10) Uani d . 1 . C C13A .2827(4) .6051(4) 1.1114(3) .0710(10) Uani d . 1 . C C14A .2346(4) .7076(4) 1.1764(3) .0638(9) Uani d . 1 . C C15A .0858(4) .7851(5) 1.1217(3) .0770(10) Uani d . 1 . C H5 .207(3) .997(3) .507(2) .063(9) Uiso d . 1 . H H6 .184(3) .871(3) .678(2) .053(8) Uiso d . 1 . H H7 -.086(3) .549(3) .688(3) .070(10) Uiso d . 1 . H H8 -.248(4) .541(3) .559(3) .080(10) Uiso d . 1 . H H9 -.251(4) .692(3) .372(3) .080(10) Uiso d . 1 . H H10 -.085(3) .842(3) .322(2) .062(9) Uiso d . 1 . H H11 .409(3) .904(3) .415(2) .054(8) Uiso d . 1 . H H12 .407(3) .654(3) .429(3) .080(10) Uiso d . 1 . H H13 .392(3) .517(3) .638(3) .070(10) Uiso d . 1 . H H14 .395(3) .687(3) .744(3) .069(9) Uiso d . 1 . H H15A .428(3) .927(4) .607(3) .080(10) Uiso d . 1 . H H15B .561(4) .796(3) .591(3) .080(10) Uiso d . 1 . H H5A .208(3) .993(3) 1.005(2) .054(8) Uiso d . 1 . H H6A .296(3) .893(3) 1.172(2) .050(8) Uiso d . 1 . H H7A .752(4) .642(3) 1.134(3) .080(10) Uiso d . 1 . H H8A .907(4) .646(4) .978(3) .090(10) Uiso d . 1 . H H9A .825(4) .777(4) .801(3) .090(10) Uiso d . 1 . H H10A .572(4) .897(4) .774(3) .090(10) Uiso d . 1 . H H11A .077(3) .862(3) .941(3) .080(10) Uiso d . 1 . H H12A .252(4) .634(4) .946(3) .090(10) Uiso d . 1 . H H13A .348(4) .517(4) 1.134(3) .090(10) Uiso d . 1 . H H14A .235(3) .670(3) 1.258(2) .065(9) Uiso d . 1 . H H15C .045(4) .878(4) 1.137(3) .090(10) Uiso d . 1 . H H15D .021(4) .713(4) 1.142(3) .090(10) 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 O1 .072(2) .114(2) .0410(10) -.0300(10) -.0050(10) -.0030(10) C2 .0360(10) .051(2) .0430(10) -.0010(10) .0030(10) -.0180(10) C6 .046(2) .060(2) .046(2) -.0030(10) .0000(10) -.0300(10) C3 .0370(10) .049(2) .0440(10) .0010(10) -.0020(10) -.0200(10) C1 .040(2) .066(2) .043(2) -.0010(10) .0020(10) -.0180(10) O2 .080(2) 0..087(2) .0510(10) -.0240(10) -.0060(10) .0020(10) C4 .048(2) .051(2) .043(2) -.0010(10) .0010(10) -.0140(10) C5 .053(2) .043(2) .054(2) -.0070(10) .0020(10) -.0220(10) C12 .039(2) .067(2) .066(2) -.0070(10) .0050(10) -.036(2) C14 .044(2) .073(2) .049(2) -.0080(10) -.0060(10) -.024(2) C7 .047(2) .070(2) .061(2) -.012(2) .0010(10) -.017(2) C13 .040(2) .055(2) .074(2) -.0020(10) .0000(10) -.021(2) C11 .052(2) .060(2) .053(2) -.0220(10) .0070(10) -.0190(10) C10 .052(2) .065(2) .051(2) .001(2) -.0060(10) -.023(2) C15 .052(2) .082(3) .076(2) -.025(2) -.001(2) -.038(2) C9 .051(2) .091(3) .075(2) -.012(2) -.013(2) -.040(2) C8 .055(2) .080(3) .086(3) -.025(2) .000(2) -.030(2) O1A .084(2) .124(2) .0430(10) -.034(2) -.0210(10) .0030(10) C4A .061(2) .044(2) .043(2) -.0170(10) -.0100(10) -.0060(10) O2A .082(2) .092(2) .0460(10) -.0130(10) -.0170(10) .0040(10) C2A .047(2) .043(2) .052(2) -.0170(10) -.0070(10) -.0120(10) C3A .054(2) 0..045(2) .044(2) -.0190(10) -.0020(10) -.0140(10) C6A .058(2) .057(2) .041(2) -.0180(10) .0000(10) -.0200(10) C1A .060(2) .056(2) .039(2) -.0240(10) -.0110(10) -.0040(10) C5A .051(2) .046(2) .049(2) -.0060(10) -.0050(10) -.0130(10) C12A .086(3) .077(2) .062(2) -.047(2) .005(2) -.031(2) C7A .054(2) .063(2) .079(3) -.016(2) -.014(2) -.017(2) C10A .076(2) .077(2) .050(2) -.037(2) .012(2) -.028(2) C14A .073(2) .085(2) .042(2) -.043(2) .002(2) -.013(2) C9A .064(2) .100(3) .098(3) -.038(2) .032(2) -.062(3) C11A .055(2) .087(3) .053(2) -.026(2) -.0090(10) -.018(2) C13A .083(3) .055(2) .078(3) -.035(2) -.004(2) -.012(2) C8A .051(2) .073(3) .117(4) -.017(2) .004(2) -.046(2) C15A .059(2) .112(3) .070(2) -.036(2) .008(2) -.030(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 O1 C1 . 1.217(3) ? C2 C7 . 1.387(4) ? C2 C3 . 1.395(4) ? C2 C1 . 1.498(4) ? C6 C1 . 1.495(4) ? C6 C5 . 1.544(4) ? C6 C14 . 1.564(4) ? C6 H6 . .94(3) ? C3 C10 . 1.402(4) ? C3 C4 . 1.474(4) ? O2 C4 . 1.221(3) ? C4 C5 . 1.503(4) ? C5 C11 . 1.569(4) ? C5 H5 . 1.01(3) ? C12 C13 . 1.319(4) ? C12 C11 . 1.493(4) ? C12 H12 . .98(3) ? C14 C13 . 1.509(4) ? C14 C15 . 1.517(4) ? C14 H14 . .95(3) ? C7 C8 . 1.384(4) ? C7 H7 . .95(3) ? C13 H13 . .99(3) ? C11 C15 . 1.529(4) ? C11 H11 . .98(3) ? C10 C9 . 1.363(5) ? C10 H10 . .91(3) ? C15 H15A . 1.01(3) ? C15 H15B . 1.01(3) ? C9 C8 . 1.376(5) ? C9 H9 . .94(3) ? C8 H8 . .98(3) ? O1A C1A . 1.218(3) ? C4A O2A . 1.223(3) ? C4A C3A . 1.480(4) ? C4A C5A . 1.488(4) ? C2A C7A . 1.396(4) ? C2A C3A . 1.401(4) ? C2A C1A . 1.481(4) ? C3A C10A . 1.393(4) ? C6A C1A . 1.492(4) ? C6A C5A . 1.540(4) ? C6A C14A . 1.559(4) ? C6A H6A . .95(3) ? C5A C11A . 1.566(4) ? C5A H5A . .94(3) ? C12A C13A . 1.327(5) ? C12A C11A . 1.490(5) ? C12A H12A . .95(3) ? C7A C8A . 1.363(5) ? C7A H7A . .95(3) ? C10A C9A . 1.371(5) ? C10A H10A . .94(3) ? C14A C13A . 1.496(5) ? C14A C15A . 1.522(5) ? C14A H14A . .97(3) ? C9A C8A . 1.384(5) ? C9A H9A . .98(4) ? C11A C15A . 1.531(5) ? C11A H11A . .97(3) ? C13A H13A . .93(3) ? C8A H8A . .95(4) ? C15A H15C . 1.01(4) ? C15A H15D . 1.02(3) ?