#------------------------------------------------------------------------------
#$Date: 2011-09-28 17:24:46 +0300 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/24/2012469.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_2012469
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o63
_journal_page_last  o65
_publ_section_title
;
D-secoestrone derivatives. V.
3-Methoxy-17-oxo-17-phenyl-16,17-secoestra-1,3,5(10)-triene-16-carbonitrile
and
17-hydroxy-3-methoxy-17-phenyl-16,17-secoestra-1,3,5(10)-triene-16-carbonitrile
;
_space_group_IT_number           4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_[local]_cod_cif_authors_sg_H-M  'P 21'
loop_
_publ_author_name
  "Lazar, Du\<san"
  "Stankovi\'c, Slobodanka"
  "Pejanovi\'c, Vjera"
  'Courseille, Christiane'
_chemical_formula_moiety  'C25 H29 N O2'
_chemical_formula_sum  'C25 H29 N O2'
_chemical_formula_weight  375.49
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  9.8063(5)
_cell_length_b  6.6970(10)
_cell_length_c  16.2010(10)
_cell_angle_alpha  90
_cell_angle_beta  101.455(5)
_cell_angle_gamma  90
_cell_volume  1042.8(2)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.196
_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
  C1  -.1651(3)  .2509(5)  .51905(15)  .0636(7) Uani d . 1 . . C
  H1  -.1081  .1397  .5194  .076 Uiso calc R 1 . . H
  C2  -.2664(3)  .2896(5)  .44843(16)  .0685(8) Uani d . 1 . . C
  H2  -.2770  .2043  .4023  .082 Uiso calc R 1 . . H
  C3  -.3516(2)  .4532(5)  .44593(14)  .0582(7) Uani d . 1 . . C
  C4  -.3357(3)  .5779(5)  .51486(14)  .0583(6) Uani d . 1 . . C
  H4  -.3936  .6884  .5138  .070 Uiso calc R 1 . . H
  C5  -.2332(3)  .5394(4)  .58647(14)  .0557(6) Uani d . 1 . . C
  C6  -.2231(3)  .6806(6)  .66030(17)  .0749(9) Uani d . 1 . . C
  H61  -.3162  .7178  .6664  .097 Uiso calc R 1 . . H
  H62  -.1753  .8012  .6488  .097 Uiso calc R 1 . . H
  C7  -.1460(3)  .5896(5)  .74251(15)  .0626(7) Uani d . 1 . . C
  H71  -.2038  .4885  .7613  .081 Uiso calc R 1 . . H
  H72  -.1271  .6924  .7854  .081 Uiso calc R 1 . . H
  C8  -.0093(2)  .4958(4)  .73078(13)  .0450(5) Uani d . 1 . . C
  H8  .0410  .5972  .7051  .054 Uiso calc R 1 . . H
  C9  -.0399(2)  .3217(4)  .66851(14)  .0484(5) Uani d . 1 . . C
  H9  -.0816  .2157  .6971  .058 Uiso calc R 1 . . H
  C10  -.1461(2)  .3746(4)  .58975(14)  .0506(6) Uani d . 1 . . C
  C11  .0963(2)  .2384(5)  .65113(14)  .0564(6) Uani d . 1 . . C
  H111  .1436  .3406  .6249  .073 Uiso calc R 1 . . H
  H112  .0770  .1267  .6125  .073 Uiso calc R 1 . . H
  C12  .1902(2)  .1695(4)  .73294(14)  .0507(5) Uani d . 1 . . C
  H121  .2768  .1203  .7202  .066 Uiso calc R 1 . . H
  H122  .1455  .0589  .7557  .066 Uiso calc R 1 . . H
  C13  .2240(2)  .3329(3)  .80088(12)  .0394(4) Uani d . 1 . . C
  C14  .0858(2)  .4313(3)  .81380(13)  .0395(4) Uani d . 1 . . C
  H14  .0352  .3320  .8404  .047 Uiso calc R 1 . . H
  C15  .1166(2)  .6125(4)  .87453(14)  .0450(5) Uani d . 1 . . C
  H151  .2085  .5958  .9094  .059 Uiso calc R 1 . . H
  H152  .1182  .7328  .8414  .059 Uiso calc R 1 . . H
  C16  .0167(2)  .6392(4)  .92895(13)  .0462(5) Uani d . 1 . . C
  C17  .2993(2)  .2347(3)  .88560(13)  .0448(5) Uani d . 1 . . C
  H17  .3029  .3341  .9304  .067 Uiso calc R 1 . . H
  C18  .3203(2)  .4899(4)  .77390(15)  .0502(5) Uani d . 1 . . C
  H181  .3953  .4242  .7546  .075 Uiso calc R 1 . . H
  H182  .3574  .5740  .8210  .075 Uiso calc R 1 . . H
  H183  .2686  .5697  .7292  .075 Uiso calc R 1 . . H
  C19  -.5366(3)  .6472(6)  .36771(17)  .0779(9) Uani d . 1 . . C
  H191  -.5933  .6382  .4095  .117 Uiso calc R 1 . . H
  H192  -.5952  .6531  .3127  .117 Uiso calc R 1 . . H
  H193  -.4804  .7656  .3772  .117 Uiso calc R 1 . . H
  C20  .4465(2)  .1687(3)  .88570(13)  .0436(5) Uani d . 1 . . C
  C21  .5583(3)  .2929(4)  .91538(15)  .0579(6) Uani d . 1 . . C
  H21  .5428  .4174  .9372  .070 Uiso calc R 1 . . H
  C22  .6928(3)  .2345(5)  .91305(18)  .0691(8) Uani d . 1 . . C
  H22  .7663  .3215  .9320  .083 Uiso calc R 1 . . H
  C23  .7190(3)  .0499(6)  .88322(17)  .0683(8) Uani d . 1 . . C
  H23  .8095  .0114  .8817  .082 Uiso calc R 1 . . H
  C24  .6096(3)  -.0778(5)  .85558(18)  .0656(7) Uani d . 1 . . C
  H24  .6263  -.2043  .8361  .079 Uiso calc R 1 . . H
  C25  .4743(3)  -.0184(4)  .85671(16)  .0557(6) Uani d . 1 . . C
  H25  .4011  -.1058  .8377  .067 Uiso calc R 1 . . H
  N  -.0595(2)  .6586(4)  .97240(13)  .0650(6) Uani d . 1 . . N
  O1  -.44920(19)  .4769(4)  .37312(10)  .0712(6) Uani d . 1 . . O
  O2  .2201(2)  .0691(3)  .90528(12)  .0638(5) Uani d . 1 . . O
  H1O2  .1806  .0999  .9436  .096 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
  C1  .0653(14)  .077(2)  .0491(12)  .0078(15)  .0117(11)  -.0219(14)
  C2  .0705(15)  .090(2)  .0452(12)  .0045(17)  .0122(11)  -.0229(15)
  C3  .0518(12)  .0831(19)  .0411(11)  -.0064(14)  .0122(9)  -.0075(13)
  C4  .0572(13)  .0707(17)  .0466(12)  .0063(14)  .0095(10)  -.0074(13)
  C5  .0581(13)  .0643(17)  .0444(11)  .0057(13)  .0097(10)  -.0130(12)
  C6  .0799(17)  .080(2)  .0576(14)  .0309(18)  -.0037(13)  -.0240(16)
  C7  .0593(13)  .0772(19)  .0499(12)  .0211(14)  .0076(10)  -.0220(13)
  C8  .0514(11)  .0428(12)  .0428(10)  .0037(10)  .0142(9)  -.0092(10)
  C9  .0529(11)  .0507(14)  .0435(11)  .0020(11)  .0140(9)  -.0143(10)
  C10  .0504(11)  .0586(15)  .0443(11)  .0011(12)  .0129(9)  -.0129(12)
  C11  .0586(13)  .0658(16)  .0456(11)  .0123(13)  .0126(10)  -.0192(12)
  C12  .0584(12)  .0455(13)  .0498(11)  .0090(11)  .0145(10)  -.0128(11)
  C13  .0483(10)  .0358(10)  .0371(9)  .0005(9)  .0159(8)  -.0003(9)
  C14  .0456(10)  .0350(10)  .0412(10)  -.0021(9)  .0164(8)  -.0074(9)
  C15  .0495(11)  .0413(12)  .0467(11)  -.0021(10)  .0155(9)  -.0113(10)
  C16  .0524(11)  .0445(12)  .0419(10)  .0055(10)  .0098(9)  -.0073(9)
  C17  .0617(12)  .0356(11)  .0411(10)  -.0019(10)  .0194(9)  .0006(9)
  C18  .0524(11)  .0500(13)  .0531(11)  -.0003(11)  .0222(10)  .0108(11)
  C19  .0698(16)  .106(3)  .0551(14)  .008(2)  .0069(12)  .0041(18)
  C20  .0562(12)  .0371(11)  .0369(9)  .0030(10)  .0075(9)  .0018(9)
  C21  .0684(15)  .0468(13)  .0516(12)  .0003(12)  -.0050(11)  -.0059(11)
  C22  .0524(14)  .072(2)  .0735(17)  -.0015(14)  -.0111(12)  .0004(16)
  C23  .0567(14)  .080(2)  .0645(15)  .0119(15)  .0037(12)  .0020(16)
  C24  .0667(15)  .0576(17)  .0711(16)  .0150(14)  .0099(13)  -.0091(14)
  C25  .0606(13)  .0414(13)  .0653(14)  .0014(12)  .0127(11)  -.0093(12)
  N  .0706(13)  .0733(16)  .0566(12)  .0075(13)  .0264(10)  -.0106(12)
  O1  .0641(10)  .1052(17)  .0415(8)  .0040(12)  .0040(7)  -.0068(11)
  O2  .0857(12)  .0448(9)  .0729(11)  -.0028(10)  .0447(10)  .0111(9)
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 O2 . 10.119(2) yes
  C1 C2 . 1.383(4) no
  C1 C10 . 1.396(3) no
  C1 H1 .  .9300 no
  C2 C3 . 1.373(4) no
  C2 H2 .  .9300 no
  C3 O1 . 1.373(3) no
  C3 C4 . 1.378(4) no
  C4 C5 . 1.400(3) no
  C4 H4 .  .9300 no
  C5 C10 . 1.390(4) no
  C5 C6 . 1.513(4) no
  C6 C7 . 1.522(4) no
  C6 H61 .  .9700 no
  C6 H62 .  .9700 no
  C7 C8 . 1.526(3) no
  C7 H71 .  .9700 no
  C7 H72 .  .9700 no
  C8 C9 . 1.532(3) no
  C8 C14 . 1.539(3) no
  C8 H8 .  .9800 no
  C9 C10 . 1.520(3) no
  C9 C11 . 1.525(3) no
  C9 H9 .  .9800 no
  C11 C12 . 1.527(3) no
  C11 H111 .  .9700 no
  C11 H112 .  .9700 no
  C12 C13 . 1.541(3) no
  C12 H121 .  .9700 no
  C12 H122 .  .9700 no
  C13 C18 . 1.534(3) no
  C13 C14 . 1.558(3) no
  C13 C17 . 1.568(3) no
  C14 C15 . 1.553(3) no
  C14 H14 .  .9800 no
  C15 C16 . 1.454(3) no
  C15 H151 .  .9700 no
  C15 H152 .  .9700 no
  C16 N . 1.131(3) no
  C17 O2 . 1.426(3) no
  C17 C20 . 1.509(3) no
  C17 H17 .  .9800 no
  C18 H181 .  .9600 no
  C18 H182 .  .9600 no
  C18 H183 .  .9600 no
  C19 O1 . 1.419(4) no
  C19 H191 .  .9600 no
  C19 H192 .  .9600 no
  C19 H193 .  .9600 no
  C20 C25 . 1.384(3) no
  C20 C21 . 1.384(3) no
  C21 C22 . 1.384(4) no
  C21 H21 .  .9300 no
  C22 C23 . 1.370(5) no
  C22 H22 .  .9300 no
  C23 C24 . 1.375(4) no
  C23 H23 .  .9300 no
  C24 C25 . 1.389(4) no
  C24 H24 .  .9300 no
  C25 H25 .  .9300 no
  O2 H1O2 .  .8200 no
_cod_database_code 2012469