data_2008315
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  585
_journal_page_last  586
_publ_section_title
;
5,10-Dimethoxy-1,4-methano-1,4,4a,11a-tetrahydrobenzo[b]fluoren-11-one oxime
;
loop_
_publ_author_name
  'Kandasamy Chinnakali'
  'Hoong-Kun Fun'
  'Dipakranjan Mal'
  'Nirmal Kumar Hazra'
  'Sujit Kumar Ghorai'
  'Gur Dayal Nigam'
_chemical_formula_sum  'C20 H19 N O3'
_chemical_formula_weight  321.36
_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  8.8166(6)
_cell_length_b  9.9326(6)
_cell_length_c  9.9764(6)
_cell_angle_alpha  76.875(2)
_cell_angle_beta  76.5820(10)
_cell_angle_gamma  74.3310(10)
_cell_volume  805.52(9)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.325
_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
  O1 0.22559(19) 0.62930(18) 1.33959(17) 0.0561(4) Uani d . 1 . . O
  O2 0.33088(18) 0.34486(17) 0.89261(14) 0.0490(4) Uani d . 1 . . O
  O3 0.4778(2) -0.04310(16) 1.17449(17) 0.0556(4) Uani d . 1 . . O
  N1 0.4292(2) 0.09597(18) 1.10147(18) 0.0432(4) Uani d . 1 . . N
  C1 0.2635(2) 0.5585(2) 1.2274(2) 0.0407(5) Uani d . 1 . . C
  C2 0.2471(2) 0.6385(2) 1.0916(2) 0.0423(5) Uani d . 1 . . C
  C3 0.2729(2) 0.5651(2) 0.9780(2) 0.0410(5) Uani d . 1 . . C
  C4 0.3133(2) 0.4144(2) 1.0027(2) 0.0388(4) Uani d . 1 . . C
  C5 0.3352(2) 0.3403(2) 1.13343(19) 0.0360(4) Uani d . 1 . . C
  C6 0.3855(2) 0.1869(2) 1.1836(2) 0.0376(4) Uani d . 1 . . C
  C7 0.3827(2) 0.1595(2) 1.3398(2) 0.0409(5) Uani d . 1 . . C
  H7 0.4894 0.1123 1.3613 0.049 Uiso calc R 1 . . H
  C8 0.2541(3) 0.0800(2) 1.4325(2) 0.0534(6) Uani d . 1 . . C
  H8 0.2854 -0.0240 1.4460 0.064 Uiso calc R 1 . . H
  C9 0.1020(3) 0.1480(3) 1.3756(3) 0.0607(7) Uani d . 1 . . C
  H9A 0.0532 0.1070 1.3272 0.073 Uiso calc R 1 . . H
  C10 0.0500(3) 0.2786(3) 1.4076(2) 0.0571(6) Uani d . 1 . . C
  H10A -0.0407 0.3454 1.3840 0.069 Uiso calc R 1 . . H
  C11 0.1647(3) 0.2978(2) 1.4884(2) 0.0497(5) Uani d . 1 . . C
  H11 0.1225 0.3711 1.5472 0.060 Uiso calc R 1 . . H
  C12 0.3250(2) 0.3095(2) 1.3825(2) 0.0406(5) Uani d . 1 . . C
  H12 0.4029 0.3274 1.4282 0.049 Uiso calc R 1 . . H
  C13 0.3076(2) 0.4132(2) 1.2477(2) 0.0376(4) Uani d . 1 . . C
  C14 0.2164(3) 0.1453(3) 1.5658(2) 0.0590(6) Uani d . 1 . . C
  H14A 0.1303 0.1136 1.6352 0.071 Uiso calc R 1 . . H
  H14B 0.3099 0.1310 1.6074 0.071 Uiso calc R 1 . . H
  C15 0.2039(3) 0.7892(2) 1.0657(3) 0.0561(6) Uani d . 1 . . C
  H15A 0.1847 0.8385 1.1391 0.067 Uiso calc R 1 . . H
  C16 0.1905(3) 0.8623(3) 0.9333(3) 0.0672(7) Uani d . 1 . . C
  H16A 0.1627 0.9611 0.9174 0.081 Uiso calc R 1 . . H
  C17 0.2181(3) 0.7902(3) 0.8218(3) 0.0639(7) Uani d . 1 . . C
  H17A 0.2099 0.8414 0.7323 0.077 Uiso calc R 1 . . H
  C18 0.2568(3) 0.6461(3) 0.8428(2) 0.0522(6) Uani d . 1 . . C
  H18A 0.2731 0.5997 0.7677 0.063 Uiso calc R 1 . . H
  C19 0.3554(3) 0.6537(3) 1.3830(3) 0.0689(8) Uani d . 1 . . C
  H19A 0.3164 0.6998 1.4632 0.103 Uiso calc R 1 . . H
  H19B 0.4097 0.7133 1.3084 0.103 Uiso calc R 1 . . H
  H19C 0.4285 0.5648 1.4071 0.103 Uiso calc R 1 . . H
  C20 0.1861(3) 0.3092(3) 0.8872(3) 0.0701(8) Uani d . 1 . . C
  H20A 0.2060 0.2539 0.8149 0.105 Uiso calc R 1 . . H
  H20B 0.1061 0.3946 0.8674 0.105 Uiso calc R 1 . . H
  H20C 0.1488 0.2550 0.9757 0.105 Uiso calc R 1 . . H
  H1O3 0.513(3) -0.089(3) 1.099(3) 0.082(9) 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 0.0582(9) 0.0532(10) 0.0611(10) -0.0080(7) -0.0020(8) -0.0336(8)
  O2 0.0522(9) 0.0615(10) 0.0349(7) -0.0092(7) -0.0063(6) -0.0177(7)
  O3 0.0783(11) 0.0351(9) 0.0459(9) 0.0039(7) -0.0090(8) -0.0149(7)
  N1 0.0501(10) 0.0365(10) 0.0406(9) -0.0012(7) -0.0074(7) -0.0140(7)
  C1 0.0375(10) 0.0404(11) 0.0458(11) -0.0066(8) -0.0039(8) -0.0174(9)
  C2 0.0352(10) 0.0393(11) 0.0514(12) -0.0076(8) -0.0076(9) -0.0075(9)
  C3 0.0323(9) 0.0456(12) 0.0434(11) -0.0097(8) -0.0065(8) -0.0042(9)
  C4 0.0352(9) 0.0458(12) 0.0352(9) -0.0065(8) -0.0043(8) -0.0126(8)
  C5 0.0344(9) 0.0385(11) 0.0354(9) -0.0041(8) -0.0054(8) -0.0132(8)
  C6 0.0367(9) 0.0394(11) 0.0375(10) -0.0024(8) -0.0078(8) -0.0145(8)
  C7 0.0457(11) 0.0382(11) 0.0378(10) 0.0026(8) -0.0135(8) -0.0134(8)
  C8 0.0796(16) 0.0370(12) 0.0402(11) -0.0109(11) -0.0042(11) -0.0095(9)
  C9 0.0591(14) 0.0794(19) 0.0497(13) -0.0310(13) 0.0002(11) -0.0154(12)
  C10 0.0449(12) 0.0691(17) 0.0482(13) -0.0069(11) 0.0005(10) -0.0088(11)
  C11 0.0642(14) 0.0446(12) 0.0337(10) 0.0000(10) -0.0036(9) -0.0141(9)
  C12 0.0491(11) 0.0378(11) 0.0370(10) -0.0009(9) -0.0150(8) -0.0143(8)
  C13 0.0388(10) 0.0392(11) 0.0367(10) -0.0059(8) -0.0078(8) -0.0134(8)
  C14 0.0833(17) 0.0487(14) 0.0369(11) -0.0060(12) -0.0057(11) -0.0078(10)
  C15 0.0513(13) 0.0409(13) 0.0752(16) -0.0080(10) -0.0106(12) -0.0123(11)
  C16 0.0613(15) 0.0433(14) 0.089(2) -0.0107(12) -0.0190(14) 0.0084(13)
  C17 0.0560(14) 0.0598(16) 0.0673(16) -0.0143(12) -0.0199(12) 0.0159(13)
  C18 0.0462(12) 0.0584(15) 0.0484(12) -0.0129(10) -0.0125(10) 0.0034(10)
  C19 0.0784(18) 0.0798(19) 0.0635(16) -0.0289(15) -0.0060(13) -0.0366(14)
  C20 0.0690(16) 0.088(2) 0.0691(17) -0.0166(15) -0.0240(14) -0.0348(15)
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 . 1.384(2) yes
  O1 C19 . 1.408(3) yes
  O2 C4 . 1.384(2) yes
  O2 C20 . 1.430(3) yes
  O3 N1 . 1.411(2) yes
  N1 C6 . 1.279(2) yes
  C1 C13 . 1.370(3) ?
  C1 C2 . 1.424(3) ?
  C2 C15 . 1.419(3) ?
  C2 C3 . 1.426(3) ?
  C3 C4 . 1.419(3) ?
  C3 C18 . 1.422(3) ?
  C4 C5 . 1.373(3) ?
  C5 C13 . 1.426(2) ?
  C5 C6 . 1.469(3) ?
  C6 C7 . 1.516(3) ?
  C7 C8 . 1.559(3) ?
  C7 C12 . 1.561(3) ?
  C8 C9 . 1.506(4) ?
  C8 C14 . 1.540(3) ?
  C9 C10 . 1.339(4) yes
  C10 C11 . 1.503(3) ?
  C11 C14 . 1.535(3) ?
  C11 C12 . 1.570(3) ?
  C12 C13 . 1.508(3) ?
  C15 C16 . 1.371(4) ?
  C16 C17 . 1.396(4) ?
  C17 C18 . 1.358(4) ?