data_2012515 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2002 _journal_volume 58 _journal_page_first o59 _journal_page_last o62 _publ_section_title ; Syn- and anticlinal isomers of 2a'-acetoxy-1,7'-diacetyl-7',7a'-dihydro-2-oxo- spiro[1H-indole-3(2H),2'(2a'H)oxeto[2,3-b]indole] ; loop_ _publ_author_name 'Usman, Anwar' 'Razak, Ibrahim Abdul' 'Fun, Hoong-Kun' 'Chantrapromma, Suchada' 'Zhang, Yan' 'Xu, Jian-Hua' _chemical_formula_moiety 'C22 H18 N2 O6' _chemical_formula_sum 'C22 H18 N2 O6' _chemical_formula_iupac 'C22 H18 N2 O6' _chemical_formula_weight 406.38 _chemical_melting_point 466K _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9350(4) _cell_length_b 9.1189(3) _cell_length_c 13.4690(6) _cell_angle_alpha 75.8970(10) _cell_angle_beta 89.8310(10) _cell_angle_gamma 62.2010(10) _cell_volume 933.64(7) _cell_formula_units_Z 2 _cell_measurement_temperature 183(2) _exptl_crystal_density_diffrn 1.446 _diffrn_ambient_temperature 183(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 O1 .1379(4) .7573(3) 1.08829(19) .0412(7) Uani d . 1 . . O O2 .8978(3) .7172(3) .54551(17) .0278(6) Uani d . 1 . . O O3 .2881(2) 1.0966(2) .69147(15) .0169(5) Uani d . 1 . . O O4 .0809(3) 1.0288(3) .73625(17) .0241(6) Uani d . 1 . . O O5 .3895(3) .9935(3) .91094(16) .0257(6) Uani d . 1 . . O O6 .6206(3) .7322(3) .81079(15) .0208(5) Uani d . 1 . . O N1 .6700(3) .8093(3) .63396(18) .0177(6) Uani d . 1 . . N N2 .2905(3) .7927(3) .95855(18) .0161(6) Uani d . 1 . . N C1 .3036(4) .6539(4) .9193(2) .0162(7) Uani d . 1 . . C C2 .2490(4) .5349(4) .9572(2) .0232(7) Uani d . 1 . . C H2 .1890 .5400 1.0139 .028 Uiso calc R 1 . . H C3 .2872(4) .4061(4) .9074(2) .0266(8) Uani d . 1 . . C H3 .2525 .3237 .9319 .032 Uiso calc R 1 . . H C4 .3750(4) .3980(4) .8227(3) .0249(8) Uani d . 1 . . C H4 .3981 .3115 .7907 .030 Uiso calc R 1 . . H C5 .4288(4) .5192(4) .7852(2) .0204(7) Uani d . 1 . . C H5 .4888 .5140 .7285 .025 Uiso calc R 1 . . H C6 .3918(4) .6479(4) .8335(2) .0163(7) Uani d . 1 . . C C7 .4389(4) .7880(3) .8115(2) .0143(7) Uani d . 1 . . C C8 .3714(4) .8752(4) .8985(2) .0159(7) Uani d . 1 . . C C9 .5905(4) .8711(4) .7195(2) .0151(6) Uani d . 1 . . C H9 .6096 .9623 .7329 .018 Uiso calc R 1 . . H C10 .5508(4) .7916(4) .5736(2) .0181(7) Uani d . 1 . . C C11 .5790(4) .7196(4) .4914(2) .0232(7) Uani d . 1 . . C H11 .6854 .6743 .4684 .028 Uiso calc R 1 . . H C12 .4408(4) .7178(4) .4446(2) .0259(8) Uani d . 1 . . C H12 .4561 .6707 .3891 .031 Uiso calc R 1 . . H C13 .2816(4) .7841(4) .4783(2) .0270(8) Uani d . 1 . . C H13 .1922 .7811 .4454 .032 Uiso calc R 1 . . H C14 .2553(4) .8552(4) .5617(2) .0205(7) Uani d . 1 . . C H14 .1487 .9010 .5843 .025 Uiso calc R 1 . . H C15 .3922(4) .8562(3) .6102(2) .0149(7) Uani d . 1 . . C C16 .4024(4) .9181(3) .7024(2) .0139(6) Uani d . 1 . . C C17 .8376(4) .7622(4) .6211(2) .0188(7) Uani d . 1 . . C C18 .9392(4) .7675(4) .7075(3) .0265(8) Uani d . 1 . . C H18A .9137 .7184 .7725 .040 Uiso calc R 1 . . H H18B .9102 .8848 .7021 .040 Uiso calc R 1 . . H H18C 1.0587 .7025 .7031 .040 Uiso calc R 1 . . H C19 .1236(4) 1.1386(4) .7090(2) .0181(7) Uani d . 1 . . C C20 .0160(4) 1.3268(4) .6926(2) .0245(8) Uani d . 1 . . C H20A .0785 1.3708 .7222 .037 Uiso calc R 1 . . H H20B -.0854 1.3487 .7249 .037 Uiso calc R 1 . . H H20C -.0149 1.3827 .6199 .037 Uiso calc R 1 . . H C21 .2090(4) .8345(4) 1.0465(2) .0231(8) Uani d . 1 . . C C22 .2167(5) .9747(5) 1.0823(3) .0331(9) Uani d . 1 . . C H22A .1550 1.0825 1.0304 .050 Uiso calc R 1 . . H H22B .3336 .9483 1.0943 .050 Uiso calc R 1 . . H H22C .1666 .9829 1.1452 .050 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 O1 .0612(19) .0541(17) .0320(15) -.0426(15) .0334(13) -.0209(13) O2 .0253(13) .0294(12) .0259(13) -.0099(11) .0144(10) -.0097(10) O3 .0203(12) .0129(10) .0178(11) -.0083(9) .0059(8) -.0042(8) O4 .0251(13) .0237(12) .0273(13) -.0139(11) .0100(9) -.0090(10) O5 .0407(15) .0309(13) .0180(12) -.0252(12) .0092(10) -.0110(10) O6 .0188(12) .0257(11) .0144(11) -.0098(10) .0029(8) -.0016(9) N1 .0209(14) .0228(13) .0136(13) -.0129(12) .0071(10) -.0073(11) N2 .0195(14) .0203(13) .0103(13) -.0106(11) .0055(10) -.0049(10) C1 .0193(16) .0183(14) .0095(15) -.0091(13) -.0005(11) -.0011(12) C2 .0269(18) .0236(16) .0183(17) -.0139(15) .0036(13) -.0005(13) C3 .039(2) .0221(16) .0218(18) -.0203(16) -.0001(14) .0015(14) C4 .0299(19) .0159(15) .0274(19) -.0095(14) .0004(14) -.0065(14) C5 .0227(17) .0165(15) .0179(16) -.0061(13) .0022(12) -.0048(13) C6 .0209(16) .0158(14) .0111(15) -.0093(13) .0006(11) -.0005(12) C7 .0157(16) .0164(14) .0108(15) -.0078(13) .0030(11) -.0032(12) C8 .0199(17) .0205(15) .0115(15) -.0122(13) .0033(11) -.0061(12) C9 .0184(16) .0212(15) .0115(15) -.0130(13) .0075(11) -.0067(12) C10 .0257(17) .0174(15) .0130(15) -.0131(14) .0031(12) -.0014(12) C11 .035(2) .0235(16) .0164(17) -.0177(15) .0112(13) -.0067(13) C12 .041(2) .0267(17) .0165(17) -.0193(16) .0079(14) -.0117(14) C13 .037(2) .0311(18) .0205(18) -.0211(16) .0006(14) -.0090(14) C14 .0252(18) .0242(16) .0163(16) -.0153(14) .0039(12) -.0052(13) C15 .0229(16) .0137(14) .0083(15) -.0101(13) .0034(11) -.0004(11) C16 .0156(15) .0109(13) .0162(16) -.0072(12) .0045(11) -.0040(12) C17 .0209(17) .0141(15) .0198(17) -.0090(13) .0074(12) -.0006(12) C18 .0215(18) .0305(18) .0286(19) -.0129(15) .0061(13) -.0091(15) C19 .0165(16) .0204(15) .0141(16) -.0062(14) .0022(11) -.0049(12) C20 .0228(18) .0189(16) .0260(18) -.0056(14) .0081(13) -.0054(14) C21 .0256(18) .0255(17) .0130(16) -.0075(15) .0070(13) -.0064(13) C22 .039(2) .044(2) .027(2) -.0222(18) .0178(15) -.0242(17) 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 C21 . 1.200(4) ? O2 C17 . 1.220(4) ? O3 C19 . 1.371(4) ? O3 C16 . 1.432(3) ? O4 C19 . 1.207(4) ? O5 C8 . 1.212(3) ? O6 C9 . 1.454(3) yes O6 C7 . 1.459(3) yes N1 C17 . 1.376(4) ? N1 C10 . 1.432(4) ? N1 C9 . 1.445(4) ? N2 C8 . 1.396(4) ? N2 C21 . 1.426(4) ? N2 C1 . 1.443(4) ? C1 C2 . 1.378(4) ? C1 C6 . 1.394(4) ? C2 C3 . 1.398(4) ? C2 H2 . .9300 ? C3 C4 . 1.379(5) ? C3 H3 . .9300 ? C4 C5 . 1.389(5) ? C4 H4 . .9300 ? C5 C6 . 1.385(4) ? C5 H5 . .9300 ? C6 C7 . 1.488(4) ? C7 C8 . 1.540(4) ? C7 C16 . 1.571(4) yes C9 C16 . 1.531(4) yes C9 H9 . .9800 ? C10 C11 . 1.385(4) ? C10 C15 . 1.399(4) ? C11 C12 . 1.396(5) ? C11 H11 . .9300 ? C12 C13 . 1.387(5) ? C12 H12 . .9300 ? C13 C14 . 1.395(4) ? C13 H13 . .9300 ? C14 C15 . 1.394(4) ? C14 H14 . .9300 ? C15 C16 . 1.502(4) ? C17 C18 . 1.502(4) ? C18 H18A . .9600 ? C18 H18B . .9600 ? C18 H18C . .9600 ? C19 C20 . 1.482(4) ? C20 H20A . .9600 ? C20 H20B . .9600 ? C20 H20C . .9600 ? C21 C22 . 1.502(4) ? C22 H22A . .9600 ? C22 H22B . .9600 ? C22 H22C . .9600 ?