data_2012647
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o239
_journal_page_last  o241
_publ_section_title
;
1-Acetyl-3-[1-(4-methoxyphenyl)-2-oxopropylidene]indol-2(3H)-one as a
twinned crystal
;
loop_
_publ_author_name
  'Usman, Anwar'
  'Razak, Ibrahim Abdul'
  'Fun, Hoong-Kun'
  'Chantrapromma, Suchada'
  'Zhang, Yan'
  'Xu, Jian-Hua'
_chemical_formula_moiety  'C20 H17 N O4'
_chemical_formula_sum  'C20 H17 N O4'
_chemical_formula_weight  335.35
_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  22.1109(4)
_cell_length_b  6.93080(10)
_cell_length_c  22.1109(4)
_cell_angle_alpha  90
_cell_angle_beta  95.1280(10)
_cell_angle_gamma  90
_cell_volume  3374.85(10)
_cell_formula_units_Z  8
_cell_measurement_temperature  213(2)
_exptl_crystal_density_diffrn  1.320
_diffrn_ambient_temperature  293(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
  O1A -0.09264(12) 0.7608(4) 0.58926(13) 0.0579(7) Uani d . 1 . . O
  O2A 0.09507(10) 0.6865(3) 0.62492(10) 0.0461(6) Uani d . 1 . . O
  O3A 0.20740(12) 0.4531(5) 0.57491(11) 0.0737(9) Uani d . 1 . . O
  O4A 0.28727(11) 0.7046(4) 0.30701(10) 0.0590(8) Uani d . 1 . . O
  N1A 0.00394(11) 0.7346(4) 0.56289(12) 0.0328(6) Uani d . 1 . . N
  C1A 0.06753(15) 0.7072(4) 0.57545(16) 0.0352(8) Uani d . 1 . . C
  C2A -0.01026(14) 0.7555(4) 0.49878(15) 0.0305(8) Uani d . 1 . . C
  C3A -0.06645(15) 0.7808(4) 0.46605(17) 0.0402(9) Uani d . 1 . . C
  H3A -0.1019 0.7882 0.4856 0.048 Uiso calc R 1 . . H
  C4A -0.06796(16) 0.7946(5) 0.40345(17) 0.0437(9) Uani d . 1 . . C
  H4A -0.1050 0.8120 0.3806 0.052 Uiso calc R 1 . . H
  C5A -0.01528(16) 0.7829(5) 0.37434(16) 0.0414(9) Uani d . 1 . . C
  H5A -0.0176 0.7921 0.3322 0.050 Uiso calc R 1 . . H
  C6A 0.04098(15) 0.7579(5) 0.40648(15) 0.0374(8) Uani d . 1 . . C
  H6A 0.0761 0.7502 0.3864 0.045 Uiso calc R 1 . . H
  C7A 0.04355(14) 0.7443(4) 0.46986(15) 0.0316(8) Uani d . 1 . . C
  C8A 0.09422(14) 0.7133(4) 0.51589(14) 0.0310(8) Uani d . 1 . . C
  C9A 0.15347(14) 0.6807(4) 0.51172(15) 0.0346(8) Uani d . 1 . . C
  C10A 0.18476(14) 0.6900(5) 0.45500(14) 0.0312(8) Uani d . 1 . . C
  C11A 0.19128(15) 0.8624(5) 0.42523(16) 0.0451(9) Uani d . 1 . . C
  H11A 0.1726 0.9727 0.4386 0.054 Uiso calc R 1 . . H
  C12A 0.22548(16) 0.8738(5) 0.37530(16) 0.0483(9) Uani d . 1 . . C
  H12A 0.2304 0.9914 0.3561 0.058 Uiso calc R 1 . . H
  C13A 0.25178(15) 0.7100(5) 0.35484(15) 0.0402(8) Uani d . 1 . . C
  C14A 0.24525(14) 0.5348(5) 0.38356(14) 0.0409(8) Uani d . 1 . . C
  H14A 0.2632 0.4243 0.3694 0.049 Uiso calc R 1 . . H
  C15A 0.21192(14) 0.5249(5) 0.43346(14) 0.0363(8) Uani d . 1 . . C
  H15A 0.2076 0.4072 0.4528 0.044 Uiso calc R 1 . . H
  C16A -0.03966(18) 0.7395(5) 0.60621(17) 0.0418(9) Uani d . 1 . . C
  C17A -0.01676(18) 0.7186(5) 0.67159(17) 0.0557(11) Uani d . 1 . . C
  H17A -0.0505 0.7154 0.6960 0.084 Uiso calc R 1 . . H
  H17B 0.0090 0.8261 0.6836 0.084 Uiso calc R 1 . . H
  H17C 0.0060 0.6009 0.6771 0.084 Uiso calc R 1 . . H
  C18A 0.19595(16) 0.6263(7) 0.56611(16) 0.0502(10) Uani d . 1 . . C
  C19A 0.22794(19) 0.7818(7) 0.60213(19) 0.0815(15) Uani d . 1 . . C
  H19A 0.2537 0.7259 0.6347 0.122 Uiso calc R 1 . . H
  H19B 0.1987 0.8647 0.6185 0.122 Uiso calc R 1 . . H
  H19C 0.2521 0.8554 0.5765 0.122 Uiso calc R 1 . . H
  C20A 0.2954(2) 0.8809(7) 0.27501(19) 0.0851(15) Uani d . 1 . . C
  H20A 0.3201 0.8573 0.2422 0.128 Uiso calc R 1 . . H
  H20B 0.3150 0.9740 0.3023 0.128 Uiso calc R 1 . . H
  H20C 0.2565 0.9295 0.2591 0.128 Uiso calc R 1 . . H
  O1B 0.40974(12) 0.1951(3) 0.58957(11) 0.0519(7) Uani d . 1 . . O
  O2B 0.37500(10) 0.2012(3) 0.40060(10) 0.0417(6) Uani d . 1 . . O
  O3B 0.43006(13) 0.0159(6) 0.28391(15) 0.1079(14) Uani d . 1 . . O
  O4B 0.69472(10) 0.4121(4) 0.22036(11) 0.0563(7) Uani d . 1 . . O
  N1B 0.43597(11) 0.2207(3) 0.49310(11) 0.0299(6) Uani d . 1 . . N
  C1B 0.42467(15) 0.2196(4) 0.42906(14) 0.0315(8) Uani d . 1 . . C
  C2B 0.49978(15) 0.2457(4) 0.50866(14) 0.0302(7) Uani d . 1 . . C
  C3B 0.53255(16) 0.2492(5) 0.56507(15) 0.0378(8) Uani d . 1 . . C
  H3B 0.5132 0.2342 0.6004 0.045 Uiso calc R 1 . . H
  C4B 0.59484(16) 0.2754(5) 0.56768(16) 0.0435(9) Uani d . 1 . . C
  H4B 0.6172 0.2796 0.6053 0.052 Uiso calc R 1 . . H
  C5B 0.62466(17) 0.2956(5) 0.51547(17) 0.0437(9) Uani d . 1 . . C
  H5B 0.6666 0.3125 0.5185 0.052 Uiso calc R 1 . . H
  C6B 0.59234(15) 0.2908(4) 0.45885(15) 0.0358(8) Uani d . 1 . . C
  H6B 0.6122 0.3049 0.4238 0.043 Uiso calc R 1 . . H
  C7B 0.52985(14) 0.2647(4) 0.45520(14) 0.0279(7) Uani d . 1 . . C
  C8B 0.48351(14) 0.2461(4) 0.40372(14) 0.0289(7) Uani d . 1 . . C
  C9B 0.48904(15) 0.2395(5) 0.34367(15) 0.0398(9) Uani d . 1 . . C
  C10B 0.54533(15) 0.2778(5) 0.31381(14) 0.0368(8) Uani d . 1 . . C
  C11B 0.56446(16) 0.4644(6) 0.30613(18) 0.0573(11) Uani d . 1 . . C
  H11B 0.5435 0.5654 0.3224 0.069 Uiso calc R 1 . . H
  C12B 0.61425(16) 0.5048(6) 0.27474(18) 0.0621(12) Uani d . 1 . . C
  H12B 0.6260 0.6320 0.2693 0.074 Uiso calc R 1 . . H
  C13B 0.64659(15) 0.3560(5) 0.25143(14) 0.0394(8) Uani d . 1 . . C
  C14B 0.62896(15) 0.1707(5) 0.25909(16) 0.0464(9) Uani d . 1 . . C
  H14B 0.6508 0.0700 0.2438 0.056 Uiso calc R 1 . . H
  C15B 0.57818(16) 0.1315(5) 0.28986(16) 0.0485(9) Uani d . 1 . . C
  H15B 0.5661 0.0042 0.2944 0.058 Uiso calc R 1 . . H
  C16B 0.39292(16) 0.2031(4) 0.53616(16) 0.0364(8) Uani d . 1 . . C
  C17B 0.32715(16) 0.1989(5) 0.51317(17) 0.0482(10) Uani d . 1 . . C
  H17D 0.3027 0.1986 0.5469 0.072 Uiso calc R 1 . . H
  H17E 0.3189 0.0846 0.4893 0.072 Uiso calc R 1 . . H
  H17F 0.3176 0.3107 0.4885 0.072 Uiso calc R 1 . . H
  C18B 0.43639(18) 0.1879(9) 0.29829(18) 0.0711(15) Uani d . 1 . . C
  C19B 0.3999(2) 0.3445(9) 0.2699(2) 0.114(2) Uani d . 1 . . C
  H19D 0.3785 0.2991 0.2330 0.170 Uiso calc R 1 . . H
  H19E 0.4259 0.4496 0.2610 0.170 Uiso calc R 1 . . H
  H19F 0.3712 0.3878 0.2972 0.170 Uiso calc R 1 . . H
  C20B 0.73453(18) 0.2683(6) 0.20192(19) 0.0670(12) Uani d . 1 . . C
  H20D 0.7655 0.3273 0.1803 0.101 Uiso calc R 1 . . H
  H20E 0.7121 0.1775 0.1759 0.101 Uiso calc R 1 . . H
  H20F 0.7531 0.2025 0.2370 0.101 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
  O1A 0.0334(16) 0.0607(18) 0.082(2) -0.0007(12) 0.0185(14) 0.0032(15)
  O2A 0.0418(15) 0.0531(17) 0.0431(15) -0.0020(12) 0.0015(12) -0.0003(12)
  O3A 0.072(2) 0.094(2) 0.0545(17) 0.0376(18) 0.0022(14) 0.0150(16)
  O4A 0.0522(16) 0.085(2) 0.0415(15) -0.0143(14) 0.0113(12) 0.0080(14)
  N1A 0.0240(15) 0.0250(15) 0.0505(18) -0.0022(11) 0.0092(13) -0.0029(12)
  C1A 0.035(2) 0.0218(19) 0.049(2) -0.0036(14) 0.0044(17) -0.0032(15)
  C2A 0.031(2) 0.0149(16) 0.046(2) -0.0033(12) 0.0047(16) -0.0009(14)
  C3A 0.030(2) 0.0246(18) 0.065(3) -0.0023(14) 0.0010(17) -0.0058(17)
  C4A 0.039(2) 0.035(2) 0.055(2) 0.0011(16) -0.0069(18) -0.0026(17)
  C5A 0.046(2) 0.032(2) 0.045(2) -0.0047(16) -0.0063(17) 0.0029(16)
  C6A 0.038(2) 0.0286(18) 0.045(2) -0.0049(14) 0.0022(17) 0.0026(15)
  C7A 0.033(2) 0.0156(16) 0.046(2) -0.0012(13) 0.0019(16) -0.0001(14)
  C8A 0.033(2) 0.0216(17) 0.0390(19) -0.0028(13) 0.0080(15) 0.0002(14)
  C9A 0.0311(19) 0.0316(19) 0.0414(19) 0.0013(14) 0.0042(15) 0.0018(15)
  C10A 0.0228(17) 0.0337(19) 0.0366(19) -0.0016(13) -0.0007(14) 0.0014(15)
  C11A 0.041(2) 0.037(2) 0.057(2) 0.0039(16) 0.0074(18) 0.0071(18)
  C12A 0.049(2) 0.044(2) 0.051(2) -0.0042(18) 0.0001(19) 0.0193(19)
  C13A 0.031(2) 0.055(2) 0.0353(19) -0.0093(16) 0.0015(15) 0.0030(17)
  C14A 0.0362(19) 0.045(2) 0.042(2) -0.0018(16) 0.0044(16) -0.0044(17)
  C15A 0.0363(18) 0.032(2) 0.0397(19) -0.0044(14) 0.0014(15) 0.0012(15)
  C16A 0.052(3) 0.0181(17) 0.058(2) -0.0060(15) 0.019(2) -0.0020(16)
  C17A 0.063(3) 0.047(2) 0.062(3) 0.0014(19) 0.028(2) 0.003(2)
  C18A 0.032(2) 0.078(3) 0.042(2) 0.011(2) 0.0080(16) 0.000(2)
  C19A 0.050(3) 0.140(5) 0.053(3) -0.023(3) -0.003(2) -0.019(3)
  C20A 0.083(3) 0.111(4) 0.063(3) -0.020(3) 0.016(2) 0.041(3)
  O1B 0.0644(19) 0.0552(17) 0.0373(15) 0.0026(13) 0.0108(13) -0.0002(12)
  O2B 0.0327(14) 0.0517(16) 0.0404(13) 0.0000(11) 0.0021(11) -0.0014(11)
  O3B 0.0463(18) 0.181(4) 0.098(2) -0.028(2) 0.0156(16) -0.088(3)
  O4B 0.0428(15) 0.0574(17) 0.0722(17) -0.0010(12) 0.0247(13) -0.0037(14)
  N1B 0.0312(16) 0.0244(14) 0.0346(16) 0.0057(11) 0.0053(12) -0.0008(11)
  C1B 0.037(2) 0.0274(19) 0.0301(18) 0.0045(14) 0.0025(15) -0.0006(14)
  C2B 0.038(2) 0.0166(16) 0.0356(19) 0.0052(13) -0.0004(15) -0.0054(13)
  C3B 0.053(2) 0.0247(18) 0.035(2) 0.0091(15) -0.0005(17) -0.0047(14)
  C4B 0.053(3) 0.032(2) 0.043(2) 0.0078(16) -0.0119(18) -0.0065(16)
  C5B 0.040(2) 0.030(2) 0.058(2) -0.0003(15) -0.0082(19) -0.0044(17)
  C6B 0.034(2) 0.0300(19) 0.043(2) 0.0001(14) 0.0001(16) -0.0050(15)
  C7B 0.0323(19) 0.0183(16) 0.0330(18) 0.0032(13) 0.0022(15) -0.0035(13)
  C8B 0.0307(18) 0.0227(17) 0.0330(18) 0.0004(13) 0.0019(14) -0.0022(13)
  C9B 0.041(2) 0.045(2) 0.0329(19) -0.0033(16) -0.0019(16) -0.0004(16)
  C10B 0.034(2) 0.047(2) 0.0290(18) 0.0000(16) -0.0006(15) -0.0046(16)
  C11B 0.050(2) 0.048(2) 0.079(3) -0.0097(19) 0.029(2) -0.027(2)
  C12B 0.052(2) 0.044(2) 0.096(3) -0.0138(18) 0.037(2) -0.020(2)
  C13B 0.0326(19) 0.046(2) 0.040(2) -0.0009(16) 0.0060(15) -0.0001(17)
  C14B 0.035(2) 0.046(2) 0.060(2) 0.0124(17) 0.0129(18) 0.0014(19)
  C15B 0.047(2) 0.041(2) 0.058(2) 0.0058(17) 0.0101(19) 0.0125(19)
  C16B 0.046(2) 0.0241(18) 0.040(2) 0.0055(14) 0.0109(17) -0.0007(15)
  C17B 0.039(2) 0.051(2) 0.057(2) 0.0046(17) 0.0158(19) 0.0040(19)
  C18B 0.036(2) 0.138(5) 0.040(2) -0.021(3) 0.0108(19) -0.022(3)
  C19B 0.042(3) 0.226(7) 0.068(3) -0.016(3) -0.019(2) 0.063(4)
  C20B 0.059(3) 0.075(3) 0.070(3) 0.021(2) 0.025(2) -0.004(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
  O1A C16A . 1.207(4) ?
  O2A C1A . 1.212(4) ?
  O3A C18A . 1.239(4) ?
  O4A C13A . 1.373(4) ?
  O4A C20A . 1.432(4) ?
  N1A C16A . 1.419(4) yes
  N1A C1A . 1.421(4) yes
  N1A C2A . 1.432(4) yes
  C1A C8A . 1.491(4) ?
  C2A C3A . 1.392(4) ?
  C2A C7A . 1.402(4) ?
  C3A C4A . 1.385(5) ?
  C3A H3A . 0.9300 ?
  C4A C5A . 1.383(5) ?
  C4A H4A . 0.9300 ?
  C5A C6A . 1.387(4) ?
  C5A H5A . 0.9300 ?
  C6A C7A . 1.400(4) ?
  C6A H6A . 0.9300 ?
  C7A C8A . 1.461(4) ?
  C8A C9A . 1.341(4) yes
  C9A C10A . 1.487(4) yes
  C9A C18A . 1.506(5) yes
  C10A C11A . 1.378(4) ?
  C10A C15A . 1.396(4) ?
  C11A C12A . 1.395(5) ?
  C11A H11A . 0.9300 ?
  C12A C13A . 1.371(5) ?
  C12A H12A . 0.9300 ?
  C13A C14A . 1.384(4) ?
  C14A C15A . 1.382(4) ?
  C14A H14A . 0.9300 ?
  C15A H15A . 0.9300 ?
  C16A C17A . 1.495(5) ?
  C17A H17A . 0.9600 ?
  C17A H17B . 0.9600 ?
  C17A H17C . 0.9600 ?
  C18A C19A . 1.481(5) ?
  C19A H19A . 0.9600 ?
  C19A H19B . 0.9600 ?
  C19A H19C . 0.9600 ?
  C20A H20A . 0.9600 ?
  C20A H20B . 0.9600 ?
  C20A H20C . 0.9600 ?
  O1B C16B . 1.207(4) ?
  O2B C1B . 1.223(4) ?
  O3B C18B . 1.238(5) ?
  O4B C13B . 1.373(4) ?
  O4B C20B . 1.414(4) ?
  N1B C16B . 1.410(4) yes
  N1B C1B . 1.416(4) yes
  N1B C2B . 1.433(4) yes
  C1B C8B . 1.473(4) ?
  C2B C3B . 1.385(4) ?
  C2B C7B . 1.413(4) ?
  C3B C4B . 1.385(5) ?
  C3B H3B . 0.9300 ?
  C4B C5B . 1.387(5) ?
  C4B H4B . 0.9300 ?
  C5B C6B . 1.385(5) ?
  C5B H5B . 0.9300 ?
  C6B C7B . 1.389(4) ?
  C6B H6B . 0.9300 ?
  C7B C8B . 1.468(4) ?
  C8B C9B . 1.345(4) yes
  C9B C10B . 1.484(4) yes
  C9B C18B . 1.510(5) yes
  C10B C11B . 1.376(5) ?
  C10B C15B . 1.380(5) ?
  C11B C12B . 1.381(4) ?
  C11B H11B . 0.9300 ?
  C12B C13B . 1.381(4) ?
  C12B H12B . 0.9300 ?
  C13B C14B . 1.357(4) ?
  C14B C15B . 1.391(5) ?
  C14B H14B . 0.9300 ?
  C15B H15B . 0.9300 ?
  C16B C17B . 1.497(5) ?
  C17B H17D . 0.9600 ?
  C17B H17E . 0.9600 ?
  C17B H17F . 0.9600 ?
  C18B C19B . 1.460(6) ?
  C19B H19D . 0.9600 ?
  C19B H19E . 0.9600 ?
  C19B H19F . 0.9600 ?
  C20B H20D . 0.9600 ?
  C20B H20E . 0.9600 ?
  C20B H20F . 0.9600 ?