data_2012814
_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  'C18 H17 Cl N2 O2'
_chemical_formula_sum  'C18 H17 Cl N2 O2'
_chemical_formula_iupac  'C18 H17 Cl N2 O2'
_chemical_formula_weight  328.79
_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  10.661(2)
_cell_length_b  11.690(2)
_cell_length_c  20.698(4)
_cell_angle_alpha  90
_cell_angle_beta  138.60(3)
_cell_angle_gamma  90
_cell_volume  1706.1(11)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.280
_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
  Cl 0.38166(9) 0.39708(8) 0.89412(5) 0.1006(3) Uani d . 1 . . Cl
  C1 0.7034(2) 0.27365(16) 0.82721(13) 0.0492(5) Uani d . 1 . . C
  N2 0.54952(18) 0.24601(13) 0.81398(10) 0.0468(4) Uani d . 1 . . N
  C3 0.5887(3) 0.13935(18) 0.86505(15) 0.0598(6) Uani d . 1 . . C
  H3A 0.5056 0.0781 0.8189 0.072 Uiso calc R 1 . . H
  H3B 0.5728 0.1506 0.9050 0.072 Uiso calc R 1 . . H
  C4 0.7932(3) 0.11314(19) 0.92763(15) 0.0657(6) Uani d . 1 . . C
  H4A 0.8793 0.1512 0.9905 0.079 Uiso calc R 1 . . H
  H4B 0.8173 0.0315 0.9380 0.079 Uiso calc R 1 . . H
  C5 0.8132(3) 0.15965(18) 0.86803(15) 0.0617(6) Uani d . 1 . . C
  H5A 0.7585 0.1076 0.8155 0.074 Uiso calc R 1 . . H
  H5B 0.9455 0.1722 0.9084 0.074 Uiso calc R 1 . . H
  C6 0.3931(2) 0.30874(17) 0.76166(12) 0.0481(5) Uani d . 1 . . C
  O7 0.36799(17) 0.40254(13) 0.72605(10) 0.0643(4) Uani d . 1 . . O
  C8 0.2414(2) 0.26030(17) 0.74616(13) 0.0504(5) Uani d . 1 . . C
  C9 0.2215(3) 0.2977(2) 0.80155(15) 0.0643(6) Uani d . 1 . . C
  C10 0.0791(3) 0.2580(3) 0.78564(17) 0.0836(8) Uani d . 1 . . C
  H10A 0.0692 0.2832 0.8243 0.100 Uiso calc R 1 . . H
  C11 -0.0484(3) 0.1809(3) 0.71209(19) 0.0868(8) Uani d . 1 . . C
  H11A -0.1456 0.1537 0.7007 0.104 Uiso calc R 1 . . H
  C12 -0.0343(3) 0.1436(3) 0.65522(19) 0.0818(8) Uani d . 1 . . C
  H12A -0.1222 0.0918 0.6050 0.098 Uiso calc R 1 . . H
  C13 0.1115(3) 0.1833(2) 0.67266(15) 0.0653(6) Uani d . 1 . . C
  H13A 0.1215 0.1574 0.6341 0.078 Uiso calc R 1 . . H
  C14 0.8327(3) 0.36954(18) 0.90327(14) 0.0554(5) Uani d . 1 . . C
  N15 0.7537(2) 0.45281(16) 0.90496(13) 0.0702(5) Uani d . 1 . . N
  H15A 0.8222 0.5078 0.9462 0.084 Uiso calc R 1 . . H
  H15B 0.6332 0.4527 0.8649 0.084 Uiso calc R 1 . . H
  O16 1.00387(19) 0.36549(15) 0.95883(12) 0.0816(6) Uani d . 1 . . O
  C17 0.6261(2) 0.30452(18) 0.73065(13) 0.0536(5) Uani d . 1 . . C
  C18 0.7097(3) 0.38739(19) 0.72489(15) 0.0626(5) Uani d . 1 . . C
  H18A 0.8121 0.4288 0.7804 0.075 Uiso calc R 1 . . H
  C19 0.6427(3) 0.4094(2) 0.63752(18) 0.0822(7) Uani d . 1 . . C
  H19A 0.7012 0.4648 0.6347 0.099 Uiso calc R 1 . . H
  C20 0.4912(3) 0.3501(3) 0.55536(18) 0.0923(9) Uani d . 1 . . C
  H20B 0.4459 0.3653 0.4966 0.111 Uiso calc R 1 . . H
  C21 0.4058(4) 0.2681(3) 0.55967(18) 0.1004(10) Uani d . 1 . . C
  H21A 0.3020 0.2279 0.5037 0.120 Uiso calc R 1 . . H
  C22 0.4731(3) 0.2453(3) 0.64620(16) 0.0805(7) Uani d . 1 . . C
  H22A 0.4150 0.1889 0.6485 0.097 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
  Cl 0.0938(3) 0.1270(6) 0.0864(3) -0.0225(4) 0.0692(2) -0.0389(4)
  C1 0.0447(6) 0.0371(10) 0.0613(8) -0.0065(7) 0.0385(6) -0.0074(7)
  N2 0.0467(5) 0.0363(8) 0.0534(6) 0.0006(6) 0.0364(5) 0.0016(6)
  C3 0.0611(8) 0.0419(11) 0.0704(10) 0.0077(9) 0.0476(7) 0.0142(9)
  C4 0.0575(9) 0.0440(12) 0.0708(11) 0.0074(9) 0.0409(8) 0.0088(9)
  C5 0.0513(7) 0.0428(11) 0.0805(11) -0.0018(8) 0.0463(7) -0.0077(9)
  C6 0.0503(7) 0.0414(11) 0.0473(8) 0.0045(8) 0.0350(6) 0.0032(7)
  O7 0.0657(6) 0.0481(8) 0.0733(7) 0.0113(6) 0.0505(5) 0.0162(6)
  C8 0.0445(7) 0.0473(11) 0.0539(8) 0.0083(8) 0.0353(6) 0.0084(8)
  C9 0.0520(8) 0.0764(16) 0.0595(9) 0.0073(10) 0.0404(7) 0.0054(10)
  C10 0.0649(9) 0.115(2) 0.0802(11) 0.0079(13) 0.0572(8) 0.0028(13)
  C11 0.0585(8) 0.107(2) 0.1024(13) 0.0039(13) 0.0624(9) 0.0099(14)
  C12 0.0514(9) 0.0802(18) 0.0886(14) -0.0082(12) 0.0451(10) -0.0091(13)
  C13 0.0580(8) 0.0607(14) 0.0741(10) -0.0004(10) 0.0487(8) -0.0033(10)
  C14 0.0566(8) 0.0419(11) 0.0625(9) -0.0050(9) 0.0431(7) -0.0032(8)
  N15 0.0596(7) 0.0466(10) 0.0862(10) -0.0114(8) 0.0494(7) -0.0224(8)
  O16 0.0517(6) 0.0610(10) 0.0937(9) -0.0136(7) 0.0433(6) -0.0282(8)
  C17 0.0543(7) 0.0482(12) 0.0642(9) -0.0052(8) 0.0462(6) -0.0075(8)
  C18 0.0722(8) 0.0471(12) 0.0844(10) -0.0006(9) 0.0633(7) -0.0007(9)
  C19 0.1090(10) 0.0654(16) 0.1142(13) 0.0068(12) 0.0959(9) 0.0124(11)
  C20 0.1021(11) 0.113(2) 0.0818(11) 0.0165(16) 0.0748(9) 0.0153(13)
  C21 0.0927(12) 0.141(3) 0.0726(12) -0.0289(17) 0.0635(10) -0.0227(15)
  C22 0.0844(9) 0.0936(19) 0.0757(11) -0.0385(12) 0.0636(8) -0.0278(11)
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
  Cl C9 . 1.741(2) n
  C1 N2 . 1.482(3) n
  C1 C17 . 1.528(3) n
  C1 C14 . 1.543(3) n
  C1 C5 . 1.542(3) n
  N2 C6 . 1.335(2) n
  N2 C3 . 1.478(3) n
  C3 C4 . 1.513(3) n
  C3 H3A . 0.9700 n
  C3 H3B . 0.9700 n
  C4 C5 . 1.502(4) n
  C4 H4A . 0.9700 n
  C4 H4B . 0.9700 n
  C5 H5A . 0.9700 n
  C5 H5B . 0.9700 n
  C6 O7 . 1.234(2) n
  C6 C8 . 1.504(3) n
  C8 C13 . 1.372(3) n
  C8 C9 . 1.384(3) n
  C9 C10 . 1.371(3) n
  C10 C11 . 1.369(4) n
  C10 H10A . 0.9300 n
  C11 C12 . 1.366(4) n
  C11 H11A . 0.9300 n
  C12 C13 . 1.385(3) n
  C12 H12A . 0.9300 n
  C13 H13A . 0.9300 n
  C14 O16 . 1.227(2) n
  C14 N15 . 1.305(3) n
  N15 H15A . 0.8600 n
  N15 H15B . 0.8600 n
  C17 C18 . 1.381(3) n
  C17 C22 . 1.385(3) n
  C18 C19 . 1.382(3) n
  C18 H18A . 0.9300 n
  C19 C20 . 1.364(4) n
  C19 H19A . 0.9300 n
  C20 C21 . 1.370(4) n
  C20 H20B . 0.9300 n
  C21 C22 . 1.366(4) n
  C21 H21A . 0.9300 n
  C22 H22A . 0.9300 n