data_2006246 _journal_name_full 'Acta Crystallographica' _journal_year 1997 _journal_volume C53 _publ_section_title ; 4,5,6,7,8,9-Hexamethoxyindeno[1,2,3-ij]isoquinoline ; loop_ _publ_author_name 'Scherowsky, G\"unter' 'Frackowiak, Esther' 'Adam, David' _chemical_name_common 4,5,6,7,8,9-Hexamethoxy-indeno[1,2,3-ij]isoquinoline _chemical_formula_sum 'C21 H21 N O6' _chemical_formula_weight 383.39 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.133(2) _cell_length_b 10.2247(10) _cell_length_c 20.0835(14) _cell_angle_alpha 90.00 _cell_angle_beta 107.55(2) _cell_angle_gamma 90.00 _cell_volume 3745.9(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.360 _diffrn_ambient_temperature 293(2) _refine_ls_R_factor_obs .0691 _refine_ls_wR_factor_obs .1663 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 C1 .8356(2) .8534(4) .4863(3) .0610(12) Uani d . 1 . C C2 .7804(2) .8199(3) .4290(3) .0567(11) Uani d . 1 . C C3 .7721(2) .6870(3) .4074(2) .0505(10) Uani d . 1 . C C4 .8229(2) .6028(3) .4491(2) .0467(9) Uani d . 1 . C C5 .8786(2) .6465(3) .5080(2) .0487(10) Uani d . 1 . C C6 .7184(2) .6299(3) .3499(2) .0556(11) Uani d . 1 . C C7 .7192(2) .4967(4) .3403(2) .0537(11) Uani d . 1 . C C8 .7724(2) .4119(3) .3869(2) .0501(10) Uani d . 1 . C C9 .8253(2) .4647(3) .4413(2) .0477(10) Uani d . 1 . C C10 .8884(2) .4195(3) .4993(2) .0475(10) Uani d . 1 . C C11 .9212(2) .5296(3) .5408(2) .0488(10) Uani d . 1 . C C12 .9817(2) .5198(4) .5980(2) .0565(11) Uani d . 1 . C C13 1.0122(2) .3962(4) .6178(2) .0590(11) Uani d . 1 . C C14 .9812(2) .2877(3) .5784(2) .0544(11) Uani d . 1 . C C15 .9202(2) .2969(3) .5203(2) .0487(10) Uani d . 1 . C C16 .5945(2) .6911(4) .2927(3) .0767(15) Uani d . 1 . C C17 .6890(2) .4123(5) .2266(3) .084(2) Uani d . 1 . C C18 .7182(2) .2090(4) .3954(3) .083(2) Uani d . 1 . C C19 1.1041(3) .4769(5) .7171(3) .086(2) Uani d . 1 . C C20 .9834(3) .0968(5) .6436(3) .091(2) Uani d . 1 . C C21 .9252(2) .1383(4) .4383(3) .0758(14) Uani d . 1 . C N1 .8869(2) .7694(3) .5290(2) .0580(10) Uani d . 1 . N O1 .67040(14) .7125(3) .3040(2) .0738(10) Uani d . 1 . O O2 .66578(13) .4386(3) .2854(2) .0609(8) Uani d . 1 . O O3 .76913(14) .2805(2) .3702(2) .0623(8) Uani d . 1 . O O4 1.0722(2) .3717(3) .6738(2) .0819(10) Uani d . 1 . O O5 1.01356(14) .1661(2) .5983(2) .0666(9) Uani d . 1 . O O6 .88939(13) .1854(2) .4861(2) .0580(8) Uani d . 1 . O H11 .8461 .9394 .5062 .050 Uiso d . 1 . H H21 .7461 .8874 .4032 .050 Uiso d . 1 . H H121 1.0021 .5962 .6275 .050 Uiso d . 1 . H H161 .5838 .6558 .3281 .050 Uiso d . 1 . H H162 .5817 .7338 .2545 .050 Uiso d . 1 . H H163 .5812 .6124 .2456 .080 Uiso d . 1 . H H171 .7281 .3759 .2428 .050 Uiso d . 1 . H H172 .6552 .3827 .1973 .050 Uiso d . 1 . H H173 .7011 .5056 .2088 .080 Uiso d . 1 . H H181 .7409 .1855 .4425 .050 Uiso d . 1 . H H182 .6734 .2268 .3678 .050 Uiso d . 1 . H H183 .7084 .1421 .3508 .080 Uiso d . 1 . H H191 1.1169 .5495 .6786 .050 Uiso d . 1 . H H192 1.1403 .4385 .7507 .050 Uiso d . 1 . H H193 1.0672 .5221 .7448 .080 Uiso d . 1 . H H201 1.0200 .0332 .6784 .050 Uiso d . 1 . H H202 .9451 .1066 .6436 .050 Uiso d . 1 . H H203 .9689 .0267 .6096 .080 Uiso d . 1 . H H211 .9215 .1856 .3944 .050 Uiso d . 1 . H H212 .9770 .1474 .4605 .080 Uiso d . 1 . H H213 .9059 .0520 .4325 .080 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 C1 .067(3) .034(2) .084(4) -.001(2) .025(2) .002(2) C2 .056(2) .034(2) .075(3) .002(2) .013(2) .012(2) C3 .047(2) .037(2) .063(3) .001(2) .009(2) .008(2) C4 .046(2) .036(2) .056(3) .000(2) .012(2) .001(2) C5 .045(2) .037(2) .062(3) .000(2) .014(2) .002(2) C6 .042(2) .047(2) .072(3) .005(2) .009(2) .016(2) C7 .042(2) .048(2) .064(3) -.003(2) .006(2) .001(2) C8 .047(2) .035(2) .062(3) -.001(2) .006(2) -.002(2) C9 .042(2) .035(2) .061(3) .0014(15) .007(2) .002(2) C10 .042(2) .035(2) .059(3) -.0007(15) .006(2) .002(2) C11 .042(2) .043(2) .057(3) .001(2) .010(2) .002(2) C12 .044(2) .047(2) .070(3) -.003(2) .005(2) -.001(2) C13 .044(2) .058(2) .064(3) .004(2) .001(2) .004(2) C14 .046(2) .044(2) .070(3) .007(2) .011(2) .010(2) C15 .040(2) .037(2) .066(3) -.001(2) .011(2) .004(2) C16 .050(2) .074(3) .089(4) .004(2) -.005(2) .031(3) C17 .053(3) .104(4) .079(4) .000(2) -.003(2) -.022(3) C18 .064(3) .062(3) .105(4) -.020(2) -.001(3) .008(3) C19 .076(3) .092(3) .067(3) .001(3) -.013(3) -.002(3) C20 .075(3) .080(3) .122(5) .027(3) .037(3) .049(3) C21 .073(3) .054(2) .101(4) -.005(2) .026(3) -.010(3) N1 .057(2) .037(2) .077(3) -.0051(14) .017(2) -.005(2) O1 .048(2) .057(2) .103(3) .0035(12) .003(2) .031(2) O2 .048(2) .066(2) .061(2) -.0029(12) .0045(13) -.007(2) O3 .057(2) .0432(15) .077(2) .0028(12) .0057(14) -.0094(14) O4 .060(2) .077(2) .083(2) .0114(15) -.016(2) .003(2) O5 .055(2) .050(2) .092(2) .0154(12) .017(2) .021(2) O6 .0490(14) .0365(13) .084(2) -.0005(11) .0127(14) -.0015(14) 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 C1 C2 . 1.351(6) ? C1 N1 . 1.388(5) ? C2 C3 . 1.421(5) ? C3 C4 . 1.377(5) ? C3 C6 . 1.420(6) ? C4 C5 . 1.405(5) ? C4 C9 . 1.423(5) ? C5 N1 . 1.320(5) ? C5 C11 . 1.485(5) ? C6 O1 . 1.377(4) ? C6 C7 . 1.376(5) ? C7 O2 . 1.389(5) ? C7 C8 . 1.446(5) ? C8 C9 . 1.358(5) ? C8 O3 . 1.381(4) ? C9 C10 . 1.476(5) ? C10 C15 . 1.401(5) ? C10 C11 . 1.429(5) ? C11 C12 . 1.366(5) ? C12 C13 . 1.399(5) ? C13 O4 . 1.365(5) ? C13 C14 . 1.388(6) ? C14 O5 . 1.393(4) ? C14 C15 . 1.382(6) ? C15 O6 . 1.370(4) ? C16 O1 . 1.418(5) ? C17 O2 . 1.409(6) ? C18 O3 . 1.427(5) ? C19 O4 . 1.402(6) ? C20 O5 . 1.408(5) ? C21 O6 . 1.421(5) ?