#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012812.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_2012812
_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  'C18 H18 N2 O2'
_chemical_formula_sum  'C18 H18 N2 O2'
_chemical_formula_weight  294.34
_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  11.959(2)
_cell_length_b  10.303(2)
_cell_length_c  21.489(4)
_cell_angle_alpha  90
_cell_angle_beta  145.05(3)
_cell_angle_gamma  90
_cell_volume  1516.7(12)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.289
_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 -0.0371(2) 0.65500(14) 0.68005(11) 0.0357(3) Uani d . 1 . . C
  N2 0.08982(17) 0.56065(12) 0.70601(10) 0.0386(3) Uani d . 1 . . N
  C3 0.2231(2) 0.50549(16) 0.80483(12) 0.0408(4) Uani d . 1 . . C
  C4 0.2324(3) 0.5814(2) 0.86831(15) 0.0549(5) Uani d . 1 . . C
  H4B 0.357(4) 0.612(2) 0.935(2) 0.102(8) Uiso d . 1 . . H
  H4A 0.197(4) 0.523(2) 0.887(2) 0.097(8) Uiso d . 1 . . H
  C5 0.0860(3) 0.68926(18) 0.79491(14) 0.0515(4) Uani d . 1 . . C
  H5B 0.006(3) 0.7011(19) 0.7938(16) 0.070(6) Uiso d . 1 . . H
  H5A 0.155(3) 0.769(2) 0.8207(18) 0.082(7) Uiso d . 1 . . H
  C6 -0.2286(2) 0.58553(15) 0.61218(13) 0.0396(3) Uani d . 1 . . C
  O7 -0.26259(17) 0.47483(10) 0.57911(10) 0.0528(3) Uani d . 1 . . O
  N8 -0.3505(2) 0.65171(15) 0.59320(14) 0.0508(4) Uani d . 1 . . N
  H8B -0.326(3) 0.730(2) 0.6158(15) 0.054(5) Uiso d . 1 . . H
  H8A -0.467(3) 0.6151(18) 0.5468(15) 0.056(5) Uiso d . 1 . . H
  C9 0.0408(2) 0.50055(17) 0.62371(13) 0.0434(4) Uani d . 1 . . C
  H9B -0.083(3) 0.5341(16) 0.5548(14) 0.045(4) Uiso d . 1 . . H
  H9A 0.028(2) 0.4055(17) 0.6265(13) 0.046(5) Uiso d . 1 . . H
  C10 0.1896(2) 0.52620(15) 0.64126(11) 0.0412(4) Uani d . 1 . . C
  C11 0.1923(3) 0.64239(18) 0.61001(14) 0.0509(4) Uani d . 1 . . C
  H11 0.101(3) 0.7103(18) 0.5776(14) 0.053(5) Uiso d . 1 . . H
  C12 0.3257(3) 0.6624(2) 0.62318(16) 0.0597(5) Uani d . 1 . . C
  H12 0.324(3) 0.741(2) 0.5997(16) 0.070(6) Uiso d . 1 . . H
  C13 0.4573(3) 0.5671(2) 0.66788(15) 0.0602(5) Uani d . 1 . . C
  H13 0.547(3) 0.580(2) 0.6749(18) 0.079(7) Uiso d . 1 . . H
  C14 0.4558(3) 0.4515(2) 0.69869(15) 0.0569(5) Uani d . 1 . . C
  H14 0.544(3) 0.3792(19) 0.7272(15) 0.062(5) Uiso d . 1 . . H
  C15 0.3229(2) 0.43054(18) 0.68562(14) 0.0487(4) Uani d . 1 . . C
  H15 0.316(2) 0.3487(18) 0.7048(14) 0.050(5) Uiso d . 1 . . H
  C16 -0.0823(2) 0.76929(14) 0.61646(12) 0.0355(3) Uani d . 1 . . C
  C17 -0.2595(2) 0.77757(17) 0.50444(13) 0.0447(4) Uani d . 1 . . C
  H17 -0.363(3) 0.7138(18) 0.4652(15) 0.057(5) Uiso d . 1 . . H
  C18 -0.2962(3) 0.87665(19) 0.44572(17) 0.0581(5) Uani d . 1 . . C
  H18 -0.418(3) 0.880(2) 0.3696(19) 0.079(7) Uiso d . 1 . . H
  C19 -0.1562(3) 0.96808(19) 0.49780(18) 0.0604(5) Uani d . 1 . . C
  H19 -0.186(3) 1.038(2) 0.4551(17) 0.077(6) Uiso d . 1 . . H
  C20 0.0197(3) 0.96190(18) 0.60813(19) 0.0591(5) Uani d . 1 . . C
  H20 0.122(3) 1.026(2) 0.6472(17) 0.078(6) Uiso d . 1 . . H
  C21 0.0576(3) 0.86323(16) 0.66764(15) 0.0486(4) Uani d . 1 . . C
  H21 0.182(2) 0.8586(16) 0.7458(14) 0.046(5) Uiso d . 1 . . H
  O22 0.31807(18) 0.40861(12) 0.83481(10) 0.0567(3) Uani d . 1 . . O
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 0.0360(7) 0.0325(7) 0.0326(7) 0.0002(6) 0.0269(7) -0.0005(6)
  N2 0.0336(6) 0.0361(7) 0.0307(6) 0.0033(5) 0.0234(6) 0.0010(5)
  C3 0.0307(7) 0.0425(8) 0.0366(7) -0.0023(7) 0.0250(7) 0.0067(7)
  C4 0.0472(10) 0.0718(12) 0.0384(9) 0.0024(9) 0.0336(9) 0.0072(9)
  C5 0.0593(11) 0.0464(10) 0.0391(9) -0.0028(9) 0.0384(9) -0.0039(8)
  C6 0.0453(8) 0.0337(7) 0.0437(8) -0.0009(7) 0.0372(8) 0.0018(6)
  O7 0.0538(7) 0.0341(6) 0.0694(8) -0.0068(5) 0.0503(7) -0.0080(5)
  N8 0.0534(9) 0.0416(8) 0.0700(10) -0.0106(7) 0.0531(9) -0.0126(7)
  C9 0.0352(8) 0.0416(9) 0.0347(8) 0.0015(7) 0.0249(7) -0.0050(7)
  C10 0.0336(7) 0.0440(9) 0.0302(7) -0.0010(6) 0.0230(7) -0.0075(6)
  C11 0.0529(10) 0.0452(9) 0.0475(10) 0.0034(8) 0.0397(9) -0.0021(8)
  C12 0.0644(12) 0.0597(12) 0.0523(11) -0.0098(10) 0.0473(11) -0.0075(10)
  C13 0.0470(10) 0.0851(15) 0.0454(10) -0.0071(10) 0.0373(9) -0.0098(10)
  C14 0.0433(9) 0.0738(13) 0.0462(10) 0.0095(9) 0.0352(9) -0.0002(9)
  C15 0.0425(9) 0.0499(10) 0.0419(9) 0.0060(8) 0.0323(8) 0.0011(8)
  C16 0.0356(7) 0.0326(7) 0.0386(8) 0.0013(6) 0.0305(7) 0.0004(6)
  C17 0.0415(9) 0.0466(9) 0.0382(8) -0.0015(7) 0.0311(8) 0.0014(7)
  C18 0.0585(11) 0.0633(12) 0.0482(10) 0.0120(10) 0.0428(10) 0.0167(9)
  C19 0.0763(14) 0.0512(11) 0.0800(14) 0.0156(10) 0.0694(13) 0.0216(10)
  C20 0.0634(12) 0.0448(10) 0.0855(14) -0.0044(9) 0.0643(13) 0.0029(10)
  C21 0.0376(9) 0.0440(9) 0.0514(10) -0.0019(7) 0.0339(9) 0.0002(8)
  O22 0.0497(7) 0.0534(7) 0.0586(7) 0.0163(6) 0.0427(7) 0.0226(6)
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 . 1.4740(19) n
  C1 C16 . 1.528(2) n
  C1 C6 . 1.552(2) n
  C1 C5 . 1.558(2) n
  N2 C3 . 1.351(2) n
  N2 C9 . 1.468(2) n
  C3 O22 . 1.2255(19) n
  C3 C4 . 1.495(3) n
  C4 C5 . 1.504(3) n
  C4 H4B . 0.94(3) n
  C4 H4A . 0.99(3) n
  C5 H5B . 0.94(2) n
  C5 H5A . 0.96(2) n
  C6 O7 . 1.2237(18) n
  C6 N8 . 1.335(2) n
  N8 H8B . 0.86(2) n
  N8 H8A . 0.89(2) n
  C9 C10 . 1.509(2) n
  C9 H9B . 0.953(17) n
  C9 H9A . 1.002(17) n
  C10 C11 . 1.386(2) n
  C10 C15 . 1.389(2) n
  C11 C12 . 1.388(3) n
  C11 H11 . 0.957(18) n
  C12 C13 . 1.373(3) n
  C12 H12 . 0.94(2) n
  C13 C14 . 1.370(3) n
  C13 H13 . 0.97(2) n
  C14 C15 . 1.386(3) n
  C14 H14 . 0.989(19) n
  C15 H15 . 0.972(18) n
  C16 C17 . 1.389(2) n
  C16 C21 . 1.389(2) n
  C17 C18 . 1.385(2) n
  C17 H17 . 0.979(19) n
  C18 C19 . 1.368(3) n
  C18 H18 . 0.94(2) n
  C19 C20 . 1.369(3) n
  C19 H19 . 0.98(2) n
  C20 C21 . 1.387(3) n
  C20 H20 . 0.98(2) n
  C21 H21 . 0.969(17) n