#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2012897.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2012897
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o477
_journal_page_last  o479
_publ_section_title
;
11-Methyl-12a-phenyl-
9a,12a-dihydrophenanthro[9',10':5,6][1,4]dioxino[2,3-d]oxazole and
9a-(10-hydroxyphenanthren-9-yl)-11,12a-diphenyl-
9a,12a-dihydrophenanthro[9',10':5,6][1,4]dioxino[2,3-d]oxazole
;
loop_
_publ_author_name
  'Usman, Anwar'
  'Razak, Ibrahim Abdul'
  'Fun, Hoong-Kun'
  'Chantrapromma, Suchada'
  'Zhang, Yan'
  'Xu, Jian-Hua'
_chemical_formula_moiety  'C24 H17 N O3'
_chemical_formula_sum  'C24 H17 N O3'
_chemical_formula_weight  367.39
_chemical_melting_point  439(1)K
_symmetry_cell_setting  Orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
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'
_cell_length_a  9.7633(4)
_cell_length_b  10.9896(4)
_cell_length_c  16.6210(7)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  1783.35(12)
_cell_formula_units_Z  4
_cell_measurement_temperature  213(2)
_exptl_crystal_density_diffrn  1.368
_diffrn_ambient_temperature  213(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 0.6729(3) 0.6238(2) 0.17570(14) 0.0370(7) Uani d . 1 . . O
  O2 0.6269(3) 0.7719(2) 0.30598(15) 0.0369(8) Uani d . 1 . . O
  O3 0.4103(3) 0.6924(3) 0.28999(16) 0.0454(8) Uani d . 1 . . O
  N1 0.4359(4) 0.6013(3) 0.1691(2) 0.0395(9) Uani d . 1 . . N
  C1 0.7268(4) 0.5947(3) 0.2501(2) 0.0265(9) Uani d . 1 . . C
  C2 0.8128(4) 0.4914(3) 0.2546(2) 0.0267(9) Uani d . 1 . . C
  C3 0.8365(4) 0.4169(3) 0.1876(3) 0.0360(10) Uani d . 1 . . C
  H3 0.7943 0.4353 0.1389 0.043 Uiso calc R 1 . . H
  C4 0.9200(4) 0.3181(4) 0.1925(3) 0.0476(12) Uani d . 1 . . C
  H4 0.9359 0.2702 0.1474 0.057 Uiso calc R 1 . . H
  C5 0.9812(5) 0.2895(4) 0.2652(4) 0.0546(14) Uani d . 1 . . C
  H5 1.0363 0.2207 0.2693 0.066 Uiso calc R 1 . . H
  C6 0.9611(4) 0.3618(4) 0.3311(3) 0.0502(13) Uani d . 1 . . C
  H6 1.0032 0.3408 0.3794 0.060 Uiso calc R 1 . . H
  C7 0.8803(4) 0.4652(4) 0.3285(2) 0.0317(10) Uani d . 1 . . C
  C8 0.8631(4) 0.5488(4) 0.3955(2) 0.0358(11) Uani d . 1 . . C
  C9 0.9335(5) 0.5347(5) 0.4698(3) 0.0477(12) Uani d . 1 . . C
  H9 0.9899 0.4674 0.4773 0.057 Uiso calc R 1 . . H
  C10 0.9200(5) 0.6177(5) 0.5301(3) 0.0589(15) Uani d . 1 . . C
  H10 0.9675 0.6067 0.5781 0.071 Uiso calc R 1 . . H
  C11 0.8364(5) 0.7180(5) 0.5206(3) 0.0564(14) Uani d . 1 . . C
  H11 0.8289 0.7745 0.5620 0.068 Uiso calc R 1 . . H
  C12 0.7649(5) 0.7349(4) 0.4512(2) 0.0417(11) Uani d . 1 . . C
  H12 0.7077 0.8021 0.4456 0.050 Uiso calc R 1 . . H
  C13 0.7776(4) 0.6506(4) 0.3879(2) 0.0303(9) Uani d . 1 . . C
  C14 0.7072(4) 0.6687(3) 0.3130(2) 0.0301(10) Uani d . 1 . . C
  C15 0.5178(4) 0.7603(4) 0.2525(3) 0.0346(10) Uani d . 1 . . C
  H15 0.4834 0.8416 0.2392 0.041 Uiso calc R 1 . . H
  C16 0.3698(5) 0.6071(4) 0.2343(3) 0.0413(11) Uani d . 1 . . C
  C17 0.5460(4) 0.6908(3) 0.1740(2) 0.0302(9) Uani d . 1 . . C
  C18 0.5520(4) 0.7733(4) 0.1017(2) 0.0288(9) Uani d . 1 . . C
  C19 0.4348(5) 0.8356(4) 0.0793(2) 0.0473(13) Uani d . 1 . . C
  H19 0.3533 0.8224 0.1069 0.057 Uiso calc R 1 . . H
  C20 0.4385(6) 0.9175(4) 0.0158(3) 0.0550(14) Uani d . 1 . . C
  H20 0.3594 0.9592 0.0013 0.066 Uiso calc R 1 . . H
  C21 0.5564(5) 0.9374(4) -0.0253(3) 0.0487(13) Uani d . 1 . . C
  H21 0.5585 0.9927 -0.0676 0.058 Uiso calc R 1 . . H
  C22 0.6723(5) 0.8755(5) -0.0039(3) 0.0553(14) Uani d . 1 . . C
  H22 0.7528 0.8879 -0.0326 0.066 Uiso calc R 1 . . H
  C23 0.6715(4) 0.7942(4) 0.0602(2) 0.0429(11) Uani d . 1 . . C
  H23 0.7515 0.7541 0.0749 0.052 Uiso calc R 1 . . H
  C24 0.2524(5) 0.5318(4) 0.2599(3) 0.0618(15) Uani d . 1 . . C
  H24A 0.1744 0.5830 0.2692 0.093 Uiso calc R 1 . . H
  H24B 0.2754 0.4894 0.3086 0.093 Uiso calc R 1 . . H
  H24C 0.2312 0.4738 0.2185 0.093 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 0.0383(17) 0.0472(16) 0.0254(14) 0.0200(15) -0.0043(14) -0.0010(13)
  O2 0.0447(18) 0.0379(15) 0.0281(15) 0.0144(14) -0.0037(14) -0.0060(13)
  O3 0.0397(18) 0.0591(19) 0.0374(16) 0.0076(16) 0.0132(15) -0.0066(15)
  N1 0.042(2) 0.0354(19) 0.041(2) -0.0004(18) 0.005(2) -0.0009(17)
  C1 0.024(2) 0.0299(19) 0.025(2) 0.0023(18) 0.0018(19) 0.0025(18)
  C2 0.018(2) 0.029(2) 0.033(2) -0.0047(17) 0.0049(19) 0.0025(18)
  C3 0.027(2) 0.034(2) 0.046(3) 0.002(2) 0.010(2) 0.004(2)
  C4 0.035(3) 0.038(2) 0.070(3) 0.007(2) 0.009(3) -0.004(2)
  C5 0.031(3) 0.038(3) 0.095(4) 0.014(2) 0.006(3) 0.009(3)
  C6 0.027(3) 0.050(3) 0.073(3) 0.005(2) -0.003(3) 0.023(3)
  C7 0.019(2) 0.036(2) 0.040(2) -0.0027(18) 0.001(2) 0.014(2)
  C8 0.023(2) 0.048(2) 0.036(2) -0.007(2) 0.003(2) 0.013(2)
  C9 0.031(3) 0.069(3) 0.043(3) -0.002(3) -0.008(2) 0.021(3)
  C10 0.049(3) 0.093(4) 0.035(3) -0.015(3) -0.013(3) 0.014(3)
  C11 0.054(3) 0.084(4) 0.031(3) -0.016(3) -0.005(3) -0.006(3)
  C12 0.039(3) 0.054(3) 0.032(2) -0.007(2) -0.004(2) -0.001(2)
  C13 0.023(2) 0.043(2) 0.025(2) -0.006(2) -0.0009(18) 0.0048(19)
  C14 0.030(2) 0.028(2) 0.033(2) 0.0020(19) -0.003(2) 0.0040(19)
  C15 0.038(3) 0.040(2) 0.0255(19) 0.010(2) 0.001(2) 0.001(2)
  C16 0.039(3) 0.038(2) 0.047(3) 0.011(2) 0.012(2) 0.002(2)
  C17 0.031(2) 0.031(2) 0.028(2) 0.009(2) -0.001(2) 0.0002(18)
  C18 0.029(2) 0.037(2) 0.0200(19) 0.003(2) -0.0037(19) -0.0032(17)
  C19 0.035(3) 0.068(3) 0.039(2) 0.018(3) 0.005(2) 0.009(2)
  C20 0.052(3) 0.071(3) 0.042(3) 0.030(3) 0.003(3) 0.021(3)
  C21 0.059(3) 0.049(3) 0.038(3) 0.011(3) 0.004(3) 0.011(2)
  C22 0.043(3) 0.076(3) 0.047(3) -0.007(3) 0.008(3) 0.022(3)
  C23 0.024(2) 0.066(3) 0.039(2) 0.005(2) -0.002(2) 0.008(2)
  C24 0.054(3) 0.052(3) 0.079(4) 0.000(3) 0.027(3) 0.005(3)
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 . 1.381(4) yes
  O1 C17 . 1.441(4) yes
  O2 C14 . 1.384(4) yes
  O2 C15 . 1.393(5) yes
  O3 C16 . 1.375(5) yes
  O3 C15 . 1.431(5) yes
  N1 C16 . 1.264(5) yes
  N1 C17 . 1.459(5) yes
  C1 C14 . 1.339(5) ?
  C1 C2 . 1.414(5) ?
  C2 C3 . 1.401(5) ?
  C2 C7 . 1.423(5) ?
  C3 C4 . 1.360(5) ?
  C3 H3 . 0.9300 ?
  C4 C5 . 1.385(7) ?
  C4 H4 . 0.9300 ?
  C5 C6 . 1.367(7) ?
  C5 H5 . 0.9300 ?
  C6 C7 . 1.384(6) ?
  C6 H6 . 0.9300 ?
  C7 C8 . 1.454(6) ?
  C8 C13 . 1.402(5) ?
  C8 C9 . 1.420(6) ?
  C9 C10 . 1.362(6) ?
  C9 H9 . 0.9300 ?
  C10 C11 . 1.381(7) ?
  C10 H10 . 0.9300 ?
  C11 C12 . 1.361(6) ?
  C11 H11 . 0.9300 ?
  C12 C13 . 1.407(5) ?
  C12 H12 . 0.9300 ?
  C13 C14 . 1.436(5) ?
  C15 C17 . 1.537(6) ?
  C15 H15 . 0.9800 ?
  C16 C24 . 1.476(6) ?
  C17 C18 . 1.507(5) ?
  C18 C23 . 1.375(6) ?
  C18 C19 . 1.384(6) ?
  C19 C20 . 1.387(6) ?
  C19 H19 . 0.9300 ?
  C20 C21 . 1.356(6) ?
  C20 H20 . 0.9300 ?
  C21 C22 . 1.367(6) ?
  C21 H21 . 0.9300 ?
  C22 C23 . 1.389(6) ?
  C22 H22 . 0.9300 ?
  C23 H23 . 0.9300 ?
  C24 H24A . 0.9600 ?
  C24 H24B . 0.9600 ?
  C24 H24C . 0.9600 ?