#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2012468.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_2012468
_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
;
loop_
_publ_author_name
  "Lazar, Du\<san"
  "Stankovi\'c, Slobodanka"
  "Pejanovi\'c, Vjera"
  'Courseille, Christiane'
_chemical_formula_moiety  'C25 H27 N O2'
_chemical_formula_sum  'C25 H27 N O2'
_chemical_formula_weight  373.48
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  8.1540(10)
_cell_length_b  8.602(3)
_cell_length_c  15.005(4)
_cell_angle_alpha  90
_cell_angle_beta  102.47(2)
_cell_angle_gamma  90
_cell_volume  1027.6(5)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.207
_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_thermal_displace_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  .0235(7)  .6513(7)  .6124(3)  .0923(15) Uani d . 1 . . O
  O2  .8038(9)  .6621(10)  .1508(5)  .133(2) Uani d . 1 A . O
  N  .4593(11)  .9987(10)  .0726(5)  .127(3) Uani d . 1 . . N
  C1  .3824(9)  .5628(8)  .5183(4)  .079(2) Uani d . 1 . . C
  H1  .4818  .5072  .5362  .094 Uiso calc R 1 . . H
  C2  .2731(10)  .5700(8)  .5752(5)  .079(2) Uani d . 1 . . C
  H2  .2987  .5198  .6314  .095 Uiso calc R 1 . . H
  C3  .1244(10)  .6515(9)  .5498(5)  .080(2) Uani d . 1 . . C
  C4  .0880(9)  .7269(8)  .4671(5)  .078(2) Uani d . 1 . . C
  H4  -.0116  .7828  .4503  .094 Uiso calc R 1 . . H
  C5  .1982(10)  .7206(8)  .4083(4)  .0708(18) Uani d . 1 . . C
  C6  .1493(9)  .8020(9)  .3185(4)  .090(2) Uani d . 1 . . C
  H61  .1059  .9042  .3282  .117 Uiso calc R 1 . . H
  H62  .0597  .7441  .2794  .117 Uiso calc R 1 . . H
  C7  .2962(9)  .8206(8)  .2692(4)  .081(2) Uani d . 1 . . C
  H71  .2531  .8514  .2063  .105 Uiso calc R 1 . . H
  H72  .3721  .9011  .2988  .105 Uiso calc R 1 . . H
  C8  .3902(9)  .6680(8)  .2719(4)  .0732(18) Uani d . 1 . . C
  H8  .3074  .5865  .2497  .088 Uiso calc R 1 . . H
  C9  .4739(8)  .6290(8)  .3710(4)  .0712(18) Uani d . 1 . . C
  H9  .5583  .7098  .3918  .085 Uiso calc R 1 . . H
  C10  .3479(9)  .6381(8)  .4327(4)  .0708(18) Uani d . 1 . . C
  C11  .5671(10)  .4761(9)  .3765(5)  .091(2) Uani d . 1 . . C
  H111  .4874  .3925  .3573  .118 Uiso calc R 1 . . H
  H112  .6238  .4566  .4393  .118 Uiso calc R 1 . . H
  C12  .6958(10)  .4777(11)  .3162(4)  .102(3) Uani d . 1 . . C
  H121  .7519  .3777  .3205  .133 Uiso calc R 1 . . H
  H122  .7800  .5563  .3385  .133 Uiso calc R 1 . . H
  C13  .6137(10)  .5118(9)  .2143(5)  .084(2) Uani d . 1 A . C
  C14  .5191(8)  .6671(8)  .2107(4)  .0711(18) Uani d . 1 . . C
  H14  .6026  .7474  .2341  .085 Uiso calc R 1 . . H
  C15  .4382(10)  .7101(8)  .1105(4)  .082(2) Uani d . 1 . . C
  H151  .4916  .6490  .0704  .106 Uiso calc R 1 . . H
  H152  .3205  .6814  .0983  .106 Uiso calc R 1 . . H
  C16  .4507(11)  .8713(10)  .0888(5)  .087(2) Uani d . 1 . . C
  C17  .7606(12)  .5317(13)  .1674(5)  .107(3) Uani d D 1 . . C
  C18  .4992(12)  .3829(9)  .1703(6)  .114(3) Uani d . 1 . . C
  H181  .5173  .3634  .1102  .172 Uiso calc R 1 A . H
  H182  .3845  .4128  .1663  .172 Uiso calc R 1 . . H
  H183  .5230  .2903  .2065  .172 Uiso calc R 1 . . H
  C19  -.1237(11)  .7452(12)  .5936(6)  .118(3) Uani d . 1 . . C
  H191  -.1791  .7390  .6439  .177 Uiso calc R 1 . . H
  H192  -.1981  .7087  .5391  .177 Uiso calc R 1 . . H
  H193  -.0933  .8511  .5853  .177 Uiso calc R 1 . . H
  C20A  .889(5)  .431(6)  .139(3)  .106(6) Uani d PGD  .287(6) A -1 C
  C21A  .995(7)  .478(6)  .083(4)  .137(7) Uani d PGD  .287(6) A -1 C
  H21A  .9895  .5790  .0608  .164 Uiso calc PR  .287(6) A -1 H
  C22A 1.110(7)  .374(7)  .061(4)  .168(10) Uani d PGD  .287(6) A -1 C
  H22A 1.1816  .4051  .0235  .202 Uiso calc PR  .287(6) A -1 H
  C23A 1.119(6)  .222(7)  .094(5)  .170(12) Uani d PGD  .287(6) A -1 C
  H23A 1.1958  .1528  .0792  .204 Uiso calc PR  .287(6) A -1 H
  C24A 1.012(9)  .175(7)  .150(6)  .186(14) Uani d PGD  .287(6) A -1 C
  H24A 1.0179  .0743  .1723  .223 Uiso calc PR  .287(6) A -1 H
  C25A  .897(8)  .280(7)  .172(4)  .161(9) Uani d PGD  .287(6) A -1 C
  H25A  .8258  .2482  .2096  .194 Uiso calc PR  .287(6) A -1 H
  C20B  .8545(16)  .387(2)  .1475(9)  .106(6) Uani d PGD  .71 A -2 C
  C21B  .969(2)  .419(2)  .0936(14)  .137(7) Uani d PGD  .71 A -2 C
  H21B  .9807  .5207  .0740  .164 Uiso calc PR  .713(6) A -2 H
  C22B 1.066(2)  .301(3)  .0688(15)  .168(10) Uani d PGD  .71 A -2 C
  H22B 1.1425  .3227  .0327  .202 Uiso calc PR  .713(6) A -2 H
  C23B 1.048(2)  .150(2)  .0980(16)  .170(12) Uani d PGD  .71 A -2 C
  H23B 1.1134  .0702  .0814  .204 Uiso calc PR  .713(6) A -2 H
  C24B  .934(3)  .117(2)  .1519(19)  .186(14) Uani d PGD  .71 A -2 C
  H24B  .9223  .0158  .1714  .223 Uiso calc PR  .713(6) A -2 H
  C25B  .837(3)  .236(2)  .1767(16)  .161(9) Uani d PGD  .71 A -2 C
  H25B  .7604  .2138  .2128  .194 Uiso calc PR  .713(6) A -2 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  .112(4)  .089(3)  .087(3)  .002(4)  .048(3)  .005(3)
  O2  .138(5)  .149(6)  .129(5)  .005(5)  .066(4)  .021(5)
  N  .195(8)  .097(6)  .099(5)  .020(6)  .052(5)  .025(5)
  C1  .099(6)  .070(4)  .073(5)  .005(4)  .030(4)  .004(4)
  C2  .106(6)  .063(4)  .072(4)  .007(5)  .028(4)  .008(4)
  C3  .111(6)  .062(4)  .073(5)  -.007(5)  .036(5)  -.008(4)
  C4  .094(5)  .064(4)  .078(5)  .013(4)  .025(4)  .003(4)
  C5  .091(5)  .060(4)  .061(4)  .013(4)  .015(4)  .002(3)
  C6  .109(6)  .085(5)  .079(5)  .033(5)  .030(4)  .012(4)
  C7  .115(6)  .063(4)  .066(4)  .030(4)  .025(4)  .012(3)
  C8  .100(5)  .062(4)  .060(4)  .006(4)  .020(4)  .000(3)
  C9  .089(5)  .059(4)  .069(4)  .011(4)  .024(4)  .006(3)
  C10  .098(5)  .054(4)  .061(4)  -.006(4)  .018(4)  -.003(3)
  C11  .118(6)  .080(5)  .082(5)  .034(5)  .039(4)  .016(4)
  C12  .123(7)  .114(7)  .082(5)  .038(6)  .050(5)  .019(5)
  C13  .115(6)  .063(5)  .084(5)  .009(5)  .042(5)  .000(4)
  C14  .094(5)  .062(4)  .058(4)  .006(4)  .019(4)  -.001(4)
  C15  .124(6)  .068(5)  .058(4)  .010(4)  .029(4)  -.002(3)
  C16  .130(7)  .075(6)  .061(4)  .018(5)  .032(4)  .005(4)
  C17  .121(8)  .121(8)  .084(6)  .030(7)  .033(5)  .011(6)
  C18  .171(9)  .068(5)  .119(6)  .004(6)  .065(6)  -.010(5)
  C19  .115(7)  .130(8)  .124(7)  .006(7)  .060(6)  .004(6)
  C20A  .106(9)  .155(16)  .061(5)  .045(9)  .031(6)  .024(8)
  C21A  .085(9)  .22(2)  .111(9)  .010(12)  .041(7)  -.020(13)
  C22A  .079(14)  .27(3)  .166(11)  .017(16)  .053(10)  -.037(18)
  C23A  .15(2)  .24(3)  .113(9)  .10(2)  .019(13)  -.009(17)
  C24A  .23(3)  .22(2)  .115(9)  .14(2)  .054(18)  .023(16)
  C25A  .23(2)  .162(18)  .113(8)  .127(16)  .086(12)  .048(10)
  C20B  .106(9)  .155(16)  .061(5)  .045(9)  .031(6)  .024(8)
  C21B  .085(9)  .22(2)  .111(9)  .010(12)  .041(7)  -.020(13)
  C22B  .079(14)  .27(3)  .166(11)  .017(16)  .053(10)  -.037(18)
  C23B  .15(2)  .24(3)  .113(9)  .10(2)  .019(13)  -.009(17)
  C24B  .23(3)  .22(2)  .115(9)  .14(2)  .054(18)  .023(16)
  C25B  .23(2)  .162(18)  .113(8)  .127(16)  .086(12)  .048(10)
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 . 10.3680(10)
  yes
  O1 C3 . 1.375(8) no
  O1 C19 . 1.424(9) no
  O2 C17 . 1.218(11) no
  N C16 . 1.128(9) no
  C1 C2 . 1.363(9) no
  C1 C10 . 1.410(9) no
  C1 H1 .  .9300 no
  C2 C3 . 1.380(9) no
  C2 H2 .  .9300 no
  C3 C4 . 1.375(9) no
  C4 C5 . 1.390(8) no
  C4 H4 .  .9300 no
  C5 C10 . 1.391(8) no
  C5 C6 . 1.495(9) no
  C6 C7 . 1.546(9) no
  C6 H61 .  .9700 no
  C6 H62 .  .9700 no
  C7 C8 . 1.516(9) no
  C7 H71 .  .9700 no
  C7 H72 .  .9700 no
  C8 C9 . 1.534(8) no
  C8 C14 . 1.537(8) no
  C8 H8 .  .9800 no
  C9 C11 . 1.512(9) no
  C9 C10 . 1.527(9) no
  C9 H9 .  .9800 no
  C11 C12 . 1.527(8) no
  C11 H111 .  .9700 no
  C11 H112 .  .9700 no
  C12 C13 . 1.560(10) no
  C12 H121 .  .9700 no
  C12 H122 .  .9700 no
  C13 C18 . 1.506(11) no
  C13 C17 . 1.524(11) no
  C13 C14 . 1.538(9) no
  C14 C15 . 1.550(8) no
  C14 H14 .  .9800 no
  C15 C16 . 1.433(11) no
  C15 H151 .  .9700 no
  C15 H152 .  .9700 no
  C17 C20A . 1.49(5) no
  C17 C20B . 1.53(2) no
  C18 H181 .  .9600 no
  C18 H182 .  .9600 no
  C18 H183 .  .9600 no
  C19 H191 .  .9600 no
  C19 H192 .  .9600 no
  C19 H193 .  .9600 no
  C20A C21A . 1.3900 no
  C20A C25A . 1.3900 no
  C21A C22A . 1.3900 no
  C21A H21A .  .9300 no
  C22A C23A . 1.3900 no
  C22A H22A .  .9300 no
  C23A C24A . 1.3900 no
  C23A H23A .  .9300 no
  C24A C25A . 1.3900 no
  C24A H24A .  .9300 no
  C25A H25A .  .9300 no
  C20B C21B . 1.3900 no
  C20B C25B . 1.3900 no
  C21B C22B . 1.3900 no
  C21B H21B .  .9300 no
  C22B C23B . 1.3900 no
  C22B H22B .  .9300 no
  C23B C24B . 1.3900 no
  C23B H23B .  .9300 no
  C24B C25B . 1.3900 no
  C24B H24B .  .9300 no
  C25B H25B .  .9300 no