#------------------------------------------------------------------------------
#$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202225.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_2202225
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o498
_journal_page_last  o500
_publ_section_title
;
(6R,9S,13R,14S)-7,8-Didehydro-3,7-dimethoxy-17-methyl-6-phenylmorphinan-4,6-diol
;
loop_
_publ_author_name
  'Li, Chun-Bao'
  'Zhang,Wen-Qin'
  'Wang, Chao'
_chemical_formula_moiety  'C25 H29 N O4'
_chemical_formula_sum  'C25 H29 N O4'
_chemical_formula_iupac  'C25 H29 N O4'
_chemical_formula_weight  407.49
_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  11.710(4)
_cell_length_b  13.177(4)
_cell_length_c  14.236(5)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  2196.6(13)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.232
_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 0.3717(2) 0.0639(2) 0.8426(2) 0.0854(9) Uani d DU 1 . . O
  O2 0.22427(19) 0.08576(19) 0.98279(18) 0.0631(7) Uani d . 1 A . O
  H2 0.2952 0.0901 0.9984 0.076 Uiso d R 1 . . H
  O3 0.0416(2) -0.05640(18) 0.89809(16) 0.0593(7) Uani d . 1 . . O
  H3 0.0922 -0.0116 0.8920 0.071 Uiso d R 1 . . H
  O4 -0.1773(2) -0.05356(19) 0.82172(17) 0.0671(8) Uani d . 1 . . O
  C1 0.1483(4) 0.2160(3) 0.7274(3) 0.0626(11) Uani d . 1 A . C
  H1A 0.1326 0.2475 0.6704 0.075 Uiso calc R 1 . . H
  C2 0.2492(4) 0.1642(3) 0.7382(3) 0.0693(12) Uani d . 1 . . C
  H2A 0.3001 0.1590 0.6883 0.083 Uiso calc R 1 A . H
  C3 0.2746(3) 0.1205(3) 0.8224(3) 0.0612(11) Uani d D 1 A . C
  C4 0.1975(3) 0.1274(3) 0.8981(3) 0.0496(9) Uani d . 1 . . C
  C5 -0.0178(3) 0.0729(2) 1.0138(2) 0.0448(9) Uani d . 1 A . C
  H5A -0.0756 0.0813 1.0619 0.054 Uiso calc R 1 . . H
  H5B 0.0526 0.0532 1.0449 0.054 Uiso calc R 1 . . H
  C6 -0.0550(3) -0.0141(3) 0.9477(2) 0.0447(9) Uani d . 1 . . C
  C7 -0.1394(3) 0.0253(3) 0.8766(2) 0.0517(10) Uani d . 1 . . C
  C8 -0.1695(3) 0.1214(3) 0.8682(3) 0.0548(10) Uani d . 1 . . C
  H8A -0.2255 0.1382 0.8246 0.066 Uiso calc R 1 . . H
  C9 -0.1084(3) 0.3043(3) 0.8713(3) 0.0542(10) Uani d . 1 . . C
  H9A -0.1857 0.3221 0.8506 0.065 Uiso calc R 1 . . H
  C10 -0.0373(3) 0.2857(3) 0.7832(3) 0.0641(11) Uani d . 1 A . C
  H10A -0.0846 0.2517 0.7370 0.077 Uiso calc R 1 . . H
  H10B -0.0149 0.3507 0.7571 0.077 Uiso calc R 1 . . H
  C11 0.0695(3) 0.2223(3) 0.7998(3) 0.0527(10) Uani d . 1 . . C
  C12 0.0904(3) 0.1740(3) 0.8851(2) 0.0457(9) Uani d . 1 A . C
  C13 0.0011(3) 0.1753(3) 0.9651(2) 0.0413(8) Uani d . 1 . . C
  C14 -0.1173(3) 0.2049(2) 0.9262(3) 0.0472(9) Uani d . 1 A . C
  H14A -0.1677 0.2169 0.9800 0.057 Uiso calc R 1 . . H
  C15 0.0344(3) 0.2595(2) 1.0353(2) 0.0498(10) Uani d . 1 A . C
  H15A -0.0206 0.2613 1.0863 0.060 Uiso calc R 1 . . H
  H15B 0.1088 0.2446 1.0619 0.060 Uiso calc R 1 . . H
  C16 0.0378(3) 0.3625(2) 0.9871(3) 0.0571(10) Uani d . 1 . . C
  H16A 0.0519 0.4147 1.0336 0.069 Uiso calc R 1 A . H
  H16B 0.1004 0.3636 0.9425 0.069 Uiso calc R 1 . . H
  N17 -0.0700(2) 0.3855(2) 0.9371(2) 0.0548(8) Uani d . 1 A . N
  C17 -0.0633(4) 0.4851(3) 0.8911(3) 0.0793(14) Uani d . 1 . . C
  H17A -0.0379 0.5350 0.9356 0.119 Uiso calc R 1 A . H
  H17B -0.1373 0.5036 0.8677 0.119 Uiso calc R 1 . . H
  H17C -0.0102 0.4817 0.8398 0.119 Uiso calc R 1 . . H
  C18 -0.2516(4) -0.0313(4) 0.7467(3) 0.0975(17) Uani d . 1 . . C
  H18A -0.2706 -0.0928 0.7140 0.146 Uiso calc R 1 . . H
  H18B -0.2149 0.0149 0.7041 0.146 Uiso calc R 1 . . H
  H18C -0.3201 -0.0007 0.7707 0.146 Uiso calc R 1 . . H
  C19 0.4514(13) 0.055(2) 0.7696(10) 0.101(3) Uani d PDU 0.46(3) A 1 C
  H19A 0.4928 0.1178 0.7635 0.152 Uiso calc PR 0.46(3) A 1 H
  H19B 0.4123 0.0408 0.7119 0.152 Uiso calc PR 0.46(3) A 1 H
  H19C 0.5038 0.0012 0.7835 0.152 Uiso calc PR 0.46(3) A 1 H
  C19' 0.4234(14) 0.0118(17) 0.7662(8) 0.101(3) Uani d PDU 0.54(3) A 2 C
  H19D 0.3917 -0.0552 0.7614 0.152 Uiso calc PR 0.54(3) A 2 H
  H19E 0.5042 0.0071 0.7765 0.152 Uiso calc PR 0.54(3) A 2 H
  H19F 0.4092 0.0483 0.7090 0.152 Uiso calc PR 0.54(3) A 2 H
  C20 -0.1060(3) -0.1018(3) 1.0047(3) 0.0527(9) Uani d U 1 . . C
  C21 -0.2216(4) -0.1079(3) 1.0232(3) 0.0740(12) Uani d U 1 . . C
  H21A -0.2698 -0.0568 1.0017 0.089 Uiso calc R 1 . . H
  C22 -0.2670(5) -0.1881(4) 1.0727(4) 0.1029(17) Uani d U 1 . . C
  H22A -0.3450 -0.1901 1.0849 0.124 Uiso calc R 1 . . H
  C23 -0.1995(7) -0.2637(4) 1.1035(4) 0.117(2) Uani d U 1 . . C
  H23A -0.2313 -0.3187 1.1351 0.140 Uiso calc R 1 . . H
  C24 -0.0833(6) -0.2597(4) 1.0885(4) 0.1162(19) Uani d U 1 . . C
  H24A -0.0361 -0.3104 1.1120 0.139 Uiso calc R 1 . . H
  C25 -0.0365(4) -0.1779(3) 1.0371(3) 0.0830(14) Uani d U 1 . . C
  H25A 0.0415 -0.1756 1.0252 0.100 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 0.0539(18) 0.114(2) 0.089(2) 0.0108(18) 0.0150(16) -0.0243(19)
  O2 0.0401(14) 0.0801(19) 0.0692(19) 0.0019(13) -0.0025(13) 0.0092(16)
  O3 0.0634(16) 0.0525(14) 0.0621(17) -0.0011(13) 0.0172(14) -0.0089(14)
  O4 0.088(2) 0.0581(17) 0.0555(17) -0.0117(15) -0.0199(15) -0.0076(15)
  C1 0.075(3) 0.065(3) 0.047(2) -0.011(2) 0.009(2) 0.001(2)
  C2 0.067(3) 0.081(3) 0.060(3) -0.013(3) 0.021(2) -0.010(3)
  C3 0.043(2) 0.067(3) 0.073(3) -0.003(2) 0.012(2) -0.016(2)
  C4 0.045(2) 0.052(2) 0.052(3) -0.0075(19) 0.002(2) -0.004(2)
  C5 0.046(2) 0.047(2) 0.042(2) -0.0004(17) 0.0034(17) 0.0023(19)
  C6 0.047(2) 0.043(2) 0.044(2) 0.0019(18) 0.0052(18) -0.0010(18)
  C7 0.055(3) 0.053(3) 0.047(2) -0.009(2) -0.0022(19) -0.002(2)
  C8 0.052(2) 0.057(3) 0.056(3) -0.003(2) -0.0111(19) 0.007(2)
  C9 0.051(2) 0.047(2) 0.065(3) 0.0010(19) -0.001(2) 0.007(2)
  C10 0.072(3) 0.058(3) 0.062(3) -0.002(2) -0.002(2) 0.012(2)
  C11 0.057(3) 0.055(2) 0.046(2) -0.0063(19) 0.005(2) 0.001(2)
  C12 0.044(2) 0.046(2) 0.047(2) -0.0061(18) 0.0023(17) -0.003(2)
  C13 0.035(2) 0.044(2) 0.044(2) -0.0052(16) -0.0009(16) -0.0010(18)
  C14 0.039(2) 0.048(2) 0.055(2) -0.0012(18) -0.0010(17) 0.0049(19)
  C15 0.044(2) 0.050(2) 0.055(2) -0.0028(18) -0.0013(18) -0.003(2)
  C16 0.051(2) 0.049(2) 0.071(3) -0.0078(18) 0.001(2) -0.006(2)
  N17 0.050(2) 0.0397(18) 0.075(2) -0.0008(15) 0.0004(17) 0.0038(17)
  C17 0.083(3) 0.049(2) 0.106(4) -0.001(2) 0.010(3) 0.013(3)
  C18 0.089(4) 0.093(4) 0.110(4) 0.008(3) -0.044(3) -0.023(3)
  C19 0.087(4) 0.101(5) 0.115(3) 0.010(3) 0.022(3) -0.009(3)
  C19' 0.087(4) 0.101(5) 0.115(3) 0.010(3) 0.022(3) -0.009(3)
  C20 0.065(3) 0.047(2) 0.046(2) -0.0085(19) 0.0001(19) -0.0022(19)
  C21 0.074(3) 0.078(3) 0.070(3) -0.009(2) 0.018(2) 0.007(2)
  C22 0.109(4) 0.109(4) 0.091(4) -0.045(4) 0.023(3) 0.009(3)
  C23 0.167(6) 0.077(4) 0.106(5) -0.039(4) 0.035(4) 0.009(3)
  C24 0.161(5) 0.072(3) 0.116(4) 0.006(4) 0.022(4) 0.032(3)
  C25 0.098(3) 0.061(3) 0.089(4) 0.003(3) 0.008(3) 0.021(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 C3 . 1.390(5) y
  O1 C19 . 1.402(8) y
  O1 C19' . 1.423(8) ?
  O2 C4 . 1.361(4) y
  O2 H2 . 0.8611 ?
  O3 C6 . 1.445(4) y
  O3 H3 . 0.8405 ?
  O4 C7 . 1.374(4) y
  O4 C18 . 1.410(4) y
  C1 C2 . 1.373(5) ?
  C1 C11 . 1.385(5) ?
  C1 H1A . 0.9300 ?
  C2 C3 . 1.363(5) ?
  C2 H2A . 0.9300 ?
  C3 C4 . 1.409(5) ?
  C4 C12 . 1.409(5) ?
  C5 C13 . 1.533(4) ?
  C5 C6 . 1.546(4) ?
  C5 H5A . 0.9700 ?
  C5 H5B . 0.9700 ?
  C6 C7 . 1.508(5) y
  C6 C20 . 1.533(5) ?
  C7 C8 . 1.319(5) y
  C8 C14 . 1.505(5) y
  C8 H8A . 0.9300 ?
  C9 N17 . 1.492(4) y
  C9 C10 . 1.525(5) ?
  C9 C14 . 1.529(4) ?
  C9 H9A . 0.9800 ?
  C10 C11 . 1.522(5) y
  C10 H10A . 0.9700 ?
  C10 H10B . 0.9700 ?
  C11 C12 . 1.393(4) ?
  C12 C13 . 1.546(4) y
  C13 C14 . 1.543(4) ?
  C13 C15 . 1.544(4) ?
  C14 H14A . 0.9800 ?
  C15 C16 . 1.521(4) ?
  C15 H15A . 0.9700 ?
  C15 H15B . 0.9700 ?
  C16 N17 . 1.480(4) y
  C16 H16A . 0.9700 ?
  C16 H16B . 0.9700 ?
  N17 C17 . 1.468(4) y
  C17 H17A . 0.9600 ?
  C17 H17B . 0.9600 ?
  C17 H17C . 0.9600 ?
  C18 H18A . 0.9600 ?
  C18 H18B . 0.9600 ?
  C18 H18C . 0.9600 ?
  C19 H19A . 0.9600 ?
  C19 H19B . 0.9600 ?
  C19 H19C . 0.9600 ?
  C19' H19D . 0.9600 ?
  C19' H19E . 0.9600 ?
  C19' H19F . 0.9600 ?
  C20 C25 . 1.371(5) ?
  C20 C21 . 1.382(5) ?
  C21 C22 . 1.378(6) ?
  C21 H21A . 0.9300 ?
  C22 C23 . 1.345(7) ?
  C22 H22A . 0.9300 ?
  C23 C24 . 1.378(8) ?
  C23 H23A . 0.9300 ?
  C24 C25 . 1.414(6) ?
  C24 H24A . 0.9300 ?
  C25 H25A . 0.9300 ?
_cod_database_code 2202225