data_2012815
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o386
_journal_page_last  o388
_publ_section_title
;
1-Substituted derivatives of 2-phenyl-2-pyrrolidine carboxamides
;
loop_
_publ_author_name
  'Tamazyan, Rafael'
  'Karapetyan, Harutyun'
  'Martirisyan, Ashot'
  'Hovhannesyan, Vahagn'
  'Gasparyan, Sahak'
_chemical_formula_moiety  'C16 H16 N2 O3'
_chemical_formula_sum  'C16 H16 N2 O3'
_chemical_formula_iupac  'C16 H16 N2 O3'
_chemical_formula_weight  284.31
_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  12.665(3)
_cell_length_b  12.214(2)
_cell_length_c  9.3453(19)
_cell_angle_alpha  90
_cell_angle_beta  91.98(3)
_cell_angle_gamma  90
_cell_volume  1444.8(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.307
_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 0.35795(10) 0.92974(11) 0.66983(14) 0.0370(3) Uani d . 1 . . C
  N2 0.28449(9) 0.83592(9) 0.69242(12) 0.0393(3) Uani d . 1 . . N
  C3 0.32912(13) 0.73216(12) 0.63835(19) 0.0528(4) Uani d . 1 . . C
  H3A 0.2941 0.7103 0.5489 0.063 Uiso calc R 1 . . H
  H3B 0.3227 0.6737 0.7077 0.063 Uiso calc R 1 . . H
  C4 0.44323(13) 0.76008(13) 0.6168(2) 0.0579(5) Uani d . 1 . . C
  H4A 0.4730 0.7142 0.5437 0.070 Uiso calc R 1 . . H
  H4B 0.4850 0.7522 0.7051 0.070 Uiso calc R 1 . . H
  C5 0.43776(12) 0.87852(13) 0.56942(16) 0.0469(4) Uani d . 1 . . C
  H5A 0.4133 0.8843 0.4702 0.056 Uiso calc R 1 . . H
  H5B 0.5063 0.9136 0.5806 0.056 Uiso calc R 1 . . H
  C6 0.18955(11) 0.84671(11) 0.75226(15) 0.0407(3) Uani d . 1 . . C
  O7 0.16134(8) 0.93179(8) 0.81089(11) 0.0483(3) Uani d . 1 . . O
  C8 0.11512(12) 0.75375(12) 0.75045(16) 0.0467(4) Uani d . 1 . . C
  O9 0.12379(11) 0.66701(11) 0.65957(15) 0.0722(4) Uani d . 1 . . O
  C10 0.03949(17) 0.60068(17) 0.6846(3) 0.0778(6) Uani d . 1 . . C
  H10A 0.0256 0.5351 0.6369 0.093 Uiso calc R 1 . . H
  C11 -0.01849(16) 0.64090(19) 0.7833(3) 0.0774(6) Uani d . 1 . . C
  H11A -0.0798 0.6103 0.8181 0.093 Uiso calc R 1 . . H
  C12 0.02967(14) 0.74068(17) 0.8279(2) 0.0677(5) Uani d . 1 . . C
  H12A 0.0061 0.7880 0.8979 0.081 Uiso calc R 1 . . H
  C13 0.41766(11) 0.96223(11) 0.81232(14) 0.0400(3) Uani d . 1 . . C
  N14 0.35976(10) 0.98565(11) 0.92272(12) 0.0461(3) Uani d . 1 . . N
  H14A 0.3897 1.0049 1.0028 0.055 Uiso calc R 1 . . H
  H14B 0.2920 0.9817 0.9147 0.055 Uiso calc R 1 . . H
  O15 0.51443(8) 0.96638(12) 0.81726(12) 0.0629(4) Uani d . 1 . . O
  C16 0.30340(11) 1.02866(11) 0.59953(14) 0.0392(3) Uani d . 1 . . C
  C17 0.23334(15) 1.01476(15) 0.48449(17) 0.0613(5) Uani d . 1 . . C
  H17A 0.2134 0.9445 0.4561 0.074 Uiso calc R 1 . . H
  C18 0.19252(18) 1.10448(19) 0.4111(2) 0.0811(6) Uani d . 1 . . C
  H18A 0.1454 1.0940 0.3338 0.097 Uiso calc R 1 . . H
  C19 0.22095(17) 1.20915(17) 0.4512(2) 0.0752(6) Uani d . 1 . . C
  H19A 0.1934 1.2693 0.4016 0.090 Uiso calc R 1 . . H
  C20 0.28994(15) 1.22343(14) 0.5646(2) 0.0632(5) Uani d . 1 . . C
  H20A 0.3101 1.2938 0.5921 0.076 Uiso calc R 1 . . H
  C21 0.33032(12) 1.13408(12) 0.63933(17) 0.0484(4) Uani d . 1 . . C
  H21A 0.3764 1.1453 0.7176 0.058 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 0.0385(7) 0.0333(7) 0.0393(7) -0.0012(5) 0.0003(5) -0.0004(5)
  N2 0.0412(6) 0.0305(6) 0.0461(6) -0.0016(5) -0.0001(5) -0.0024(5)
  C3 0.0564(9) 0.0337(8) 0.0683(10) 0.0034(7) 0.0030(8) -0.0083(7)
  C4 0.0532(9) 0.0448(9) 0.0761(11) 0.0104(7) 0.0060(8) -0.0100(8)
  C5 0.0463(8) 0.0472(9) 0.0476(8) 0.0014(7) 0.0049(6) -0.0055(6)
  C6 0.0409(7) 0.0382(7) 0.0425(7) -0.0006(6) -0.0049(6) 0.0031(6)
  O7 0.0438(6) 0.0414(6) 0.0598(6) 0.0023(4) 0.0042(5) -0.0046(5)
  C8 0.0457(8) 0.0428(8) 0.0510(8) -0.0058(6) -0.0079(7) 0.0024(6)
  O9 0.0738(8) 0.0615(8) 0.0810(9) -0.0211(7) -0.0014(7) -0.0176(7)
  C10 0.0730(13) 0.0552(11) 0.1033(16) -0.0256(10) -0.0251(12) -0.0007(11)
  C11 0.0582(11) 0.0750(14) 0.0984(16) -0.0272(10) -0.0058(11) 0.0167(12)
  C12 0.0527(10) 0.0725(12) 0.0783(12) -0.0119(9) 0.0088(9) -0.0042(10)
  C13 0.0426(8) 0.0343(7) 0.0428(7) -0.0010(6) -0.0041(6) 0.0010(6)
  N14 0.0463(7) 0.0509(8) 0.0407(6) -0.0036(6) -0.0043(5) -0.0051(5)
  O15 0.0413(6) 0.0906(9) 0.0564(7) -0.0028(6) -0.0056(5) -0.0134(6)
  C16 0.0411(7) 0.0372(8) 0.0395(7) 0.0007(6) 0.0028(6) 0.0029(6)
  C17 0.0772(12) 0.0539(10) 0.0514(9) 0.0010(8) -0.0178(8) 0.0005(7)
  C18 0.0972(16) 0.0805(15) 0.0634(11) 0.0144(12) -0.0279(11) 0.0126(10)
  C19 0.0894(14) 0.0636(13) 0.0724(12) 0.0182(11) 0.0002(11) 0.0282(10)
  C20 0.0715(11) 0.0400(9) 0.0785(12) 0.0008(8) 0.0086(9) 0.0151(8)
  C21 0.0513(8) 0.0378(8) 0.0561(9) -0.0030(6) -0.0004(7) 0.0043(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 . 1.4956(18) n
  C1 C16 . 1.5288(19) n
  C1 C5 . 1.5359(19) n
  C1 C13 . 1.5599(19) n
  N2 C6 . 1.3498(19) n
  N2 C3 . 1.4834(18) n
  C3 C4 . 1.505(2) n
  C3 H3A . 0.9700 n
  C3 H3B . 0.9700 n
  C4 C5 . 1.514(2) n
  C4 H4A . 0.9700 n
  C4 H4B . 0.9700 n
  C5 H5A . 0.9700 n
  C5 H5B . 0.9700 n
  C6 O7 . 1.2335(18) n
  C6 C8 . 1.475(2) n
  C8 C12 . 1.332(2) n
  C8 O9 . 1.365(2) n
  O9 C10 . 1.367(2) n
  C10 C11 . 1.296(3) n
  C10 H10A . 0.9300 n
  C11 C12 . 1.419(3) n
  C11 H11A . 0.9300 n
  C12 H12A . 0.9300 n
  C13 O15 . 1.2260(18) n
  C13 N14 . 1.3175(19) n
  N14 H14A . 0.8600 n
  N14 H14B . 0.8600 n
  C16 C21 . 1.380(2) n
  C16 C17 . 1.381(2) n
  C17 C18 . 1.384(3) n
  C17 H17A . 0.9300 n
  C18 C19 . 1.377(3) n
  C18 H18A . 0.9300 n
  C19 C20 . 1.361(3) n
  C19 H19A . 0.9300 n
  C20 C21 . 1.384(2) n
  C20 H20A . 0.9300 n
  C21 H21A . 0.9300 n