data_2008550
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  996
_journal_page_last  1000
_publ_section_title
;
Regioselectivity in dibenzobarrelene photorearrangements:
photoproducts derived from 9-substituted-dibenzobarrelenes.
;
loop_
_publ_author_name
  'Muneer, M. '
  'Ramaiah, D.'
  ' Ajitkumar, E. S.'
  'Sajimon, M. C. '
  'Rath, Nigam P.'
  'George, M. V.'
_chemical_formula_moiety  'C30 H19 N O4'
_chemical_formula_sum  'C30 H19 N O4'
_chemical_formula_weight  457.46
_symmetry_cell_setting  Orthorhombic
_symmetry_space_group_name_H-M  'P b c a'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  '-x, y+1/2, -z+1/2'
  'x+1/2, -y+1/2, -z'
  '-x, -y, -z'
  'x-1/2, y, -z-1/2'
  'x, -y-1/2, z-1/2'
  '-x-1/2, y-1/2, z'
_cell_length_a  16.86840(10)
_cell_length_b  15.39550(10)
_cell_length_c  17.5200(2)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  4549.90(7)
_cell_formula_units_Z  8
_cell_measurement_temperature  223(2)
_exptl_crystal_density_diffrn  1.336
_diffrn_ambient_temperature  223(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  .14568(7)  .37035(7)  .23304(7)  .0474(3) Uani d . 1 . . O
  O2  .17557(7)  .27351(9)  .31723(7)  .0620(4) Uani d . 1 . . O
  O3  .00621(7)  .11113(8)  .05445(6)  .0503(3) Uani d . 1 . . O
  O4  .05818(7)  .31622(8)  .05460(6)  .0537(3) Uani d . 1 . . O
  N1  .13108(7)  .30559(8)  .27071(7)  .0361(3) Uani d . 1 . . N
  C1  -.14989(9)  .36101(10)  .25076(10)  .0417(4) Uani d . 1 . . C
  H1A  -.1936  .3561  .2178  .050 Uiso calc R 1 . . H
  C2  -.15438(11)  .41088(11)  .31658(11)  .0517(4) Uani d . 1 . . C
  H2A  -.2013  .4412  .3277  .062 Uiso calc R 1 . . H
  C3  -.09083(11)  .41663(11)  .36609(10)  .0532(5) Uani d . 1 . . C
  H3A  -.0951  .4513  .4100  .064 Uiso calc R 1 . . H
  C4  -.02078(10)  .37198(10)  .35200(9)  .0431(4) Uani d . 1 . . C
  H4A  .0216  .3738  .3868  .052 Uiso calc R 1 . . H
  C4A  -.01540(8)  .32480(9)  .28505(8)  .0332(3) Uani d . 1 . . C
  C4B  .05052(8)  .26453(9)  .25811(8)  .0311(3) Uani d . 1 . . C
  C4C  .03555(8)  .17847(9)  .29786(8)  .0315(3) Uani d . 1 . . C
  C5  .05295(9)  .15307(10)  .37183(8)  .0378(3) Uani d . 1 . . C
  H5A  .0826  .1891  .4043  .045 Uiso calc R 1 . . H
  C6  .02535(10)  .07291(11)  .39667(9)  .0423(4) Uani d . 1 . . C
  H6A  .0380  .0536  .4461  .051 Uiso calc R 1 . . H
  C7  -.02061(10)  .02093(10)  .34962(9)  .0423(4) Uani d . 1 . . C
  H7A  -.0376  -.0338  .3670  .051 Uiso calc R 1 . . H
  C8  -.04191(9)  .04880(9)  .27707(8)  .0377(3) Uani d . 1 . . C
  H8A  -.0748  .0144  .2460  .045 Uiso calc R 1 . . H
  C8A  -.01384(8)  .12849(9)  .25106(8)  .0313(3) Uani d . 1 . . C
  C8B  -.02511(8)  .17085(9)  .17531(8)  .0314(3) Uani d . 1 . . C
  C8C  .03051(8)  .24833(9)  .17189(8)  .0312(3) Uani d . 1 . . C
  C8D  -.05682(8)  .26667(9)  .16754(8)  .0335(3) Uani d . 1 . . C
  H8DA  -.0787  .2845  .1175  .040 Uiso calc R 1 . . H
  C8E  -.07933(9)  .31852(9)  .23491(8)  .0336(3) Uani d . 1 . . C
  C9  -.04189(9)  .11627(9)  .10603(8)  .0350(3) Uani d . 1 . . C
  C10  -.11984(9)  .07151(9)  .10281(8)  .0343(3) Uani d . 1 . . C
  C11  -.12851(10)  -.00045(10)  .05502(8)  .0392(3) Uani d . 1 . . C
  H11A  -.0851  -.0202  .0262  .047 Uiso calc R 1 . . H
  C12  -.20041(11)  -.04279(11)  .04979(9)  .0499(4) Uani d . 1 . . C
  H12A  -.2058  -.0914  .0178  .060 Uiso calc R 1 . . H
  C13  -.26449(11)  -.01364(12)  .09162(10)  .0542(4) Uani d . 1 . . C
  H13A  -.3136  -.0421  .0875  .065 Uiso calc R 1 . . H
  C14  -.25670(10)  .05715(12)  .13954(10)  .0520(4) Uani d . 1 . . C
  H14A  -.3005  .0766  .1680  .062 Uiso calc R 1 . . H
  C15  -.18487(10)  .09931(11)  .14560(9)  .0430(4) Uani d . 1 . . C
  H15A  -.1797  .1470  .1787  .052 Uiso calc R 1 . . H
  C16  .08393(9)  .27007(9)  .10508(8)  .0365(3) Uani d . 1 . . C
  C17  .16622(9)  .23570(10)  .10284(8)  .0360(3) Uani d . 1 . . C
  C18  .19045(9)  .16590(10)  .14753(9)  .0403(4) Uani d . 1 . . C
  H18A  .1541  .1385  .1804  .048 Uiso calc R 1 . . H
  C19  .26808(10)  .13665(12)  .14373(10)  .0492(4) Uani d . 1 . . C
  H19A  .2843  .0893  .1738  .059 Uiso calc R 1 . . H
  C20  .32162(10)  .17685(13)  .09585(11)  .0544(5) Uani d . 1 . . C
  H20A  .3744  .1574  .0939  .065 Uiso calc R 1 . . H
  C21  .29783(11)  .24557(13)  .05080(10)  .0541(4) Uani d . 1 . . C
  H21A  .3344  .2725  .0179  .065 Uiso calc R 1 . . H
  C22  .22059(10)  .27503(11)  .05378(9)  .0456(4) Uani d . 1 . . C
  H22A  .2046  .3216  .0227  .055 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  .0428(6)  .0383(6)  .0609(7)  -.0057(5)  .0019(5)  .0069(5)
  O2  .0451(7)  .0794(9)  .0613(8)  -.0167(6)  -.0195(6)  .0247(7)
  O3  .0465(7)  .0638(8)  .0405(6)  -.0001(6)  .0090(5)  -.0179(5)
  O4  .0588(7)  .0640(8)  .0383(6)  .0175(6)  .0059(5)  .0176(6)
  N1  .0352(7)  .0395(7)  .0337(6)  -.0012(5)  .0009(5)  .0001(5)
  C1  .0379(8)  .0366(8)  .0506(9)  .0032(6)  .0024(7)  -.0005(7)
  C2  .0470(10)  .0437(9)  .0645(11)  .0039(7)  .0155(9)  -.0131(8)
  C3  .0589(11)  .0478(9)  .0530(10)  -.0051(8)  .0152(9)  -.0215(8)
  C4  .0464(9)  .0437(9)  .0391(8)  -.0104(7)  .0030(7)  -.0109(7)
  C4A  .0360(8)  .0304(7)  .0331(7)  -.0038(6)  .0041(6)  -.0027(6)
  C4B  .0300(7)  .0337(7)  .0297(7)  -.0026(6)  -.0018(5)  -.0014(6)
  C4C  .0314(7)  .0338(7)  .0295(7)  .0005(6)  .0004(5)  .0002(6)
  C5  .0378(8)  .0439(8)  .0315(7)  -.0028(6)  -.0024(6)  .0015(6)
  C6  .0455(9)  .0477(9)  .0337(8)  .0019(7)  -.0011(7)  .0088(7)
  C7  .0490(9)  .0347(8)  .0434(9)  -.0009(7)  .0031(7)  .0057(7)
  C8  .0419(8)  .0330(7)  .0382(8)  -.0014(6)  .0002(6)  -.0036(6)
  C8A  .0340(7)  .0316(7)  .0283(7)  .0034(6)  .0013(6)  -.0026(5)
  C8B  .0337(7)  .0315(7)  .0288(7)  .0024(6)  -.0001(6)  -.0030(5)
  C8C  .0339(7)  .0323(7)  .0274(7)  .0023(6)  -.0013(5)  .0000(5)
  C8D  .0355(7)  .0341(7)  .0308(7)  .0044(6)  -.0033(6)  -.0014(6)
  C8E  .0359(7)  .0293(7)  .0355(7)  .0001(6)  .0012(6)  -.0010(6)
  C9  .0392(8)  .0363(7)  .0296(7)  .0084(6)  -.0030(6)  -.0051(6)
  C10  .0387(8)  .0363(7)  .0278(7)  .0045(6)  -.0046(6)  -.0036(6)
  C11  .0497(9)  .0380(8)  .0298(7)  .0057(7)  -.0033(6)  -.0034(6)
  C12  .0643(11)  .0428(9)  .0427(9)  -.0065(8)  -.0099(8)  -.0082(7)
  C13  .0475(10)  .0582(11)  .0569(10)  -.0103(8)  -.0092(8)  -.0037(9)
  C14  .0406(9)  .0622(11)  .0532(10)  .0000(8)  .0017(8)  -.0079(9)
  C15  .0423(9)  .0443(9)  .0424(9)  .0035(7)  -.0004(7)  -.0111(7)
  C16  .0439(8)  .0363(7)  .0293(7)  .0029(6)  .0021(6)  .0012(6)
  C17  .0403(8)  .0385(8)  .0291(7)  .0008(6)  .0028(6)  -.0031(6)
  C18  .0405(8)  .0448(8)  .0356(8)  .0028(7)  .0027(6)  .0017(7)
  C19  .0443(10)  .0534(10)  .0498(10)  .0075(8)  -.0047(8)  -.0005(8)
  C20  .0362(9)  .0683(12)  .0588(11)  .0024(8)  -.0001(8)  -.0090(9)
  C21  .0452(10)  .0636(11)  .0534(10)  -.0110(8)  .0123(8)  -.0030(9)
  C22  .0501(9)  .0471(9)  .0397(8)  -.0031(7)  .0064(7)  .0018(7)
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 N1 . 1.2207(16) ?
  O2 N1 . 1.2130(16) ?
  O3 C9 . 1.2171(18) ?
  O4 C16 . 1.2148(18) ?
  N1 C4B . 1.5150(18) ?
  C1 C8E . 1.386(2) ?
  C1 C2 . 1.387(2) ?
  C2 C3 . 1.382(3) ?
  C3 C4 . 1.389(2) ?
  C4 C4A . 1.383(2) ?
  C4A C8E . 1.394(2) ?
  C4A C4B . 1.523(2) ?
  C4B C4C . 1.5180(19) ?
  C4B C8C . 1.5678(19) ?
  C4C C5 . 1.385(2) ?
  C4C C8A . 1.399(2) ?
  C5 C6 . 1.389(2) ?
  C6 C7 . 1.386(2) ?
  C7 C8 . 1.389(2) ?
  C8 C8A . 1.392(2) ?
  C8A C8B . 1.4909(19) ?
  C8B C9 . 1.5031(19) ?
  C8B C8C . 1.519(2) ?
  C8B C8D . 1.5751(19) ?
  C8C C8D . 1.502(2) ?
  C8C C16 . 1.515(2) ?
  C8D C8E . 1.4748(19) ?
  C9 C10 . 1.486(2) ?
  C10 C15 . 1.396(2) ?
  C10 C11 . 1.396(2) ?
  C11 C12 . 1.380(2) ?
  C12 C13 . 1.381(3) ?
  C13 C14 . 1.382(2) ?
  C14 C15 . 1.379(2) ?
  C16 C17 . 1.486(2) ?
  C17 C18 . 1.391(2) ?
  C17 C22 . 1.395(2) ?
  C18 C19 . 1.386(2) ?
  C19 C20 . 1.379(3) ?
  C20 C21 . 1.380(3) ?
  C21 C22 . 1.380(2) ?