#------------------------------------------------------------------------------
#$Date: 2008-01-26 14:05:32 +0100 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012813.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_2012813
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o399
_journal_page_last  o401
_publ_section_title
;
1-Substituted derivatives of 2-aryl-5-oxo-2-pyrrolidine carboxylic acid
;
loop_
_publ_author_name
  'Karapetyan, Harutyun'
  'Tamazyan, Rafael'
  'Martirisyan, Ashot'
  'Hovhannesyan, Vahagn'
  'Gasparyan, Sahak'
_chemical_formula_moiety  'C21 H22 N2 O2'
_chemical_formula_sum  'C21 H22 N2 O2'
_chemical_formula_weight  334.41
_symmetry_cell_setting  'Monoclinic'
_symmetry_space_group_name_H-M  'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y-1/2, z-1/2'
_cell_length_a  7.5182(15)
_cell_length_b  25.125(5)
_cell_length_c  10.612(2)
_cell_angle_alpha  90
_cell_angle_beta  106.07(3)
_cell_angle_gamma  90
_cell_volume  1926.3(7)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.153
_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 0.4694(2) 0.35322(7) 0.97282(16) 0.0421(4) Uani d . 1 . . C
  N2 0.45809(18) 0.31272(5) 0.87004(13) 0.0422(3) Uani d . 1 . . N
  C3 0.3170(2) 0.27728(7) 0.86394(18) 0.0499(4) Uani d . 1 . . C
  C4 0.2408(3) 0.28702(10) 0.9788(2) 0.0565(5) Uani d . 1 . . C
  H4B 0.119(3) 0.3068(9) 0.945(2) 0.070(6) Uiso d . 1 . . H
  H4A 0.218(3) 0.2543(10) 1.021(2) 0.081(7) Uiso d . 1 . . H
  C5 0.3826(3) 0.32297(9) 1.06784(19) 0.0527(5) Uani d . 1 . . C
  H5B 0.334(3) 0.3477(8) 1.1171(19) 0.059(6) Uiso d . 1 . . H
  H5A 0.483(3) 0.3011(9) 1.128(2) 0.069(6) Uiso d . 1 . . H
  C6 0.3435(3) 0.39776(8) 0.9125(2) 0.0614(5) Uani d . 1 . . C
  N7 0.2384(3) 0.42897(9) 0.8638(3) 0.1005(8) Uani d . 1 . . N
  O8 0.2639(2) 0.24484(6) 0.77767(14) 0.0749(5) Uani d . 1 . . O
  C9 0.5338(2) 0.32114(7) 0.76151(16) 0.0450(4) Uani d . 1 . . C
  C10 0.4264(3) 0.34283(9) 0.64623(19) 0.0613(5) Uani d . 1 . . C
  H10 0.296(3) 0.3521(9) 0.641(2) 0.072(6) Uiso d . 1 . . H
  C11 0.5008(4) 0.34988(10) 0.5412(2) 0.0746(7) Uani d . 1 . . C
  H11 0.422(3) 0.3650(10) 0.460(2) 0.091(8) Uiso d . 1 . . H
  C12 0.6809(4) 0.33590(9) 0.5500(2) 0.0706(6) Uani d . 1 . . C
  C13 0.7859(3) 0.31389(11) 0.6659(2) 0.0725(6) Uani d . 1 . . C
  H13 0.917(3) 0.3057(10) 0.676(2) 0.084(7) Uiso d . 1 . . H
  C14 0.7128(3) 0.30627(9) 0.7710(2) 0.0595(5) Uani d . 1 . . C
  H14 0.786(3) 0.2902(9) 0.852(2) 0.068(6) Uiso d . 1 . . H
  C15 0.7614(5) 0.34374(14) 0.4349(3) 0.1120(11) Uani d . 1 . . C
  H15A 0.8739 0.3236 0.4493 0.168 Uiso calc R 1 . . H
  H15B 0.7872 0.3808 0.4268 0.168 Uiso calc R 1 . . H
  H15C 0.6740 0.3317 0.3558 0.168 Uiso calc R 1 . . H
  C16 0.6632(2) 0.37380(6) 1.03602(15) 0.0404(4) Uani d . 1 . . C
  C17 0.7079(3) 0.42681(7) 1.03542(18) 0.0515(4) Uani d . 1 . . C
  H17 0.618(3) 0.4528(9) 0.989(2) 0.071(6) Uiso d . 1 . . H
  C18 0.8823(3) 0.44570(8) 1.1015(2) 0.0569(5) Uani d . 1 . . C
  H18 0.908(3) 0.4828(10) 1.104(2) 0.075(7) Uiso d . 1 . . H
  C19 1.0153(2) 0.41069(7) 1.16977(16) 0.0466(4) Uani d . 1 . . C
  C20 0.9732(2) 0.35670(7) 1.17012(16) 0.0445(4) Uani d . 1 . . C
  H20 1.067(3) 0.3345(8) 1.2167(18) 0.050(5) Uiso d . 1 . . H
  C21 0.8000(2) 0.33879(7) 1.10394(17) 0.0437(4) Uani d . 1 . . C
  H21 0.766(3) 0.3020(8) 1.1070(18) 0.056(5) Uiso d . 1 . . H
  O22 1.19148(18) 0.42441(6) 1.23838(13) 0.0614(4) Uani d . 1 . . O
  C23 1.2387(3) 0.47973(9) 1.2584(3) 0.0751(7) Uani d . 1 . . C
  H23 1.191(3) 0.4974(10) 1.171(2) 0.087(7) Uiso d . 1 . . H
  C24 1.4478(4) 0.48140(13) 1.2958(3) 0.1030(10) Uani d . 1 . . C
  H24A 1.4909 0.4652 1.2278 0.155 Uiso calc R 1 . . H
  H24D 1.4966 0.4624 1.3764 0.155 Uiso calc R 1 . . H
  H24B 1.4887 0.5177 1.3070 0.155 Uiso calc R 1 . . H
  C25 1.1600(5) 0.50233(15) 1.3620(3) 0.1234(13) Uani d . 1 . . C
  H25D 1.0275 0.4996 1.3340 0.185 Uiso calc R 1 . . H
  H25A 1.1950 0.5391 1.3762 0.185 Uiso calc R 1 . . H
  H25B 1.2070 0.4828 1.4421 0.185 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 0.0415(8) 0.0404(9) 0.0447(9) 0.0011(7) 0.0123(7) -0.0037(7)
  N2 0.0453(7) 0.0430(8) 0.0396(7) -0.0053(6) 0.0141(6) -0.0036(6)
  C3 0.0496(10) 0.0493(10) 0.0503(10) -0.0098(8) 0.0129(8) -0.0033(8)
  C4 0.0489(11) 0.0686(13) 0.0554(11) -0.0128(10) 0.0200(9) -0.0035(10)
  C5 0.0495(10) 0.0627(12) 0.0512(11) -0.0066(9) 0.0226(9) -0.0086(9)
  C6 0.0478(10) 0.0528(11) 0.0770(14) 0.0049(9) 0.0061(9) -0.0093(10)
  N7 0.0759(13) 0.0633(13) 0.141(2) 0.0239(11) -0.0049(13) -0.0004(13)
  O8 0.0893(11) 0.0740(10) 0.0658(9) -0.0381(8) 0.0291(8) -0.0253(8)
  C9 0.0516(10) 0.0461(9) 0.0384(8) -0.0096(8) 0.0142(7) -0.0038(7)
  C10 0.0605(12) 0.0708(14) 0.0506(11) -0.0045(10) 0.0119(9) 0.0082(9)
  C11 0.0947(18) 0.0827(16) 0.0453(11) -0.0084(14) 0.0174(11) 0.0105(11)
  C12 0.0939(17) 0.0759(15) 0.0508(12) -0.0210(13) 0.0348(11) -0.0095(10)
  C13 0.0672(14) 0.0962(18) 0.0634(14) -0.0081(13) 0.0334(11) -0.0140(12)
  C14 0.0564(12) 0.0774(14) 0.0472(10) 0.0018(10) 0.0186(9) -0.0023(10)
  C15 0.154(3) 0.129(3) 0.0764(17) -0.020(2) 0.0715(19) -0.0030(17)
  C16 0.0432(8) 0.0411(9) 0.0381(8) -0.0009(7) 0.0131(7) -0.0032(7)
  C17 0.0537(10) 0.0396(9) 0.0549(10) 0.0033(8) 0.0043(8) 0.0033(8)
  C18 0.0598(11) 0.0380(10) 0.0649(12) -0.0069(8) 0.0040(9) -0.0016(8)
  C19 0.0448(9) 0.0510(10) 0.0430(9) -0.0027(8) 0.0105(7) -0.0054(7)
  C20 0.0436(9) 0.0456(10) 0.0452(9) 0.0054(8) 0.0137(7) 0.0028(7)
  C21 0.0473(9) 0.0395(9) 0.0477(9) 0.0020(7) 0.0190(7) 0.0003(7)
  O22 0.0495(7) 0.0592(8) 0.0674(9) -0.0066(6) 0.0026(6) -0.0073(6)
  C23 0.0766(15) 0.0621(14) 0.0686(14) -0.0235(11) -0.0099(12) -0.0015(11)
  C24 0.0766(17) 0.115(2) 0.101(2) -0.0424(16) -0.0033(14) 0.0027(17)
  C25 0.109(2) 0.112(2) 0.123(3) 0.0133(19) -0.0106(19) -0.062(2)
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
  C1 N2 . 1.477(2) n
  C1 C6 . 1.491(3) n
  C1 C16 . 1.516(2) n
  C1 C5 . 1.544(2) n
  N2 C3 . 1.373(2) n
  N2 C9 . 1.434(2) n
  C3 O8 . 1.208(2) n
  C3 C4 . 1.503(3) n
  C4 C5 . 1.513(3) n
  C4 H4B . 1.02(2) n
  C4 H4A . 0.97(2) n
  C5 H5B . 0.95(2) n
  C5 H5A . 1.01(2) n
  C6 N7 . 1.132(3) n
  C9 C14 . 1.374(3) n
  C9 C10 . 1.378(3) n
  C10 C11 . 1.390(3) n
  C10 H10 . 1.00(2) n
  C11 C12 . 1.376(4) n
  C11 H11 . 0.98(2) n
  C12 C13 . 1.380(3) n
  C12 C15 . 1.519(3) n
  C13 C14 . 1.386(3) n
  C13 H13 . 0.99(2) n
  C14 H14 . 0.97(2) n
  C15 H15A . 0.9600 n
  C15 H15B . 0.9600 n
  C15 H15C . 0.9600 n
  C16 C17 . 1.374(2) n
  C16 C21 . 1.393(2) n
  C17 C18 . 1.388(3) n
  C17 H17 . 0.97(2) n
  C18 C19 . 1.377(3) n
  C18 H18 . 0.95(2) n
  C19 O22 . 1.367(2) n
  C19 C20 . 1.393(3) n
  C20 C21 . 1.373(2) n
  C20 H20 . 0.927(19) n
  C21 H21 . 0.96(2) n
  O22 C23 . 1.436(3) n
  C23 C25 . 1.497(4) n
  C23 C24 . 1.512(3) n
  C23 H23 . 1.00(3) n
  C24 H24A . 0.9600 n
  C24 H24D . 0.9600 n
  C24 H24B . 0.9600 n
  C25 H25D . 0.9600 n
  C25 H25A . 0.9600 n
  C25 H25B . 0.9600 n