#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/28/2012813.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2012813
loop_
_publ_author_name
'Karapetyan, Harutyun'
'Tamazyan, Rafael'
'Martirisyan, Ashot'
'Hovhannesyan, Vahagn'
'Gasparyan, Sahak'
_publ_section_title
;
 1-Substituted derivatives of 2-aryl-5-oxopyrrolidine-2-carboxylic acid
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o399
_journal_page_last               o401
_journal_paper_doi               10.1107/S0108270102009241
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C21 H22 N2 O2'
_chemical_formula_sum            'C21 H22 N2 O2'
_chemical_formula_weight         334.41
_chemical_name_systematic
;
2-(4-isopropoxyphenyl)-5-oxo-1-(4-tolyl)pyrrolidine-2-carbonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 106.07(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5182(15)
_cell_length_b                   25.125(5)
_cell_length_c                   10.612(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.5
_cell_measurement_theta_min      14.4
_cell_volume                     1926.2(7)
_computing_cell_refinement       'SETANG in CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1988)'
_computing_data_reduction        'local program'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 1.0
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_sigmaI/netI    0.033
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5212
_diffrn_reflns_theta_full        28.0
_diffrn_reflns_theta_max         28.0
_diffrn_reflns_theta_min         1.6
_diffrn_standards_decay_%        'variation +-1.0'
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sphere
_exptl_crystal_F_000             712
_exptl_crystal_size_rad          0.17
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.20
_refine_ls_extinction_coef       0.0064(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.087
_refine_ls_R_factor_gt           0.049
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0453P)²+0.4186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.115
_refine_ls_wR_factor_ref         0.142
_reflns_number_gt                3067
_reflns_number_total             4621
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg1112.cif
_cod_data_source_block           IV
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1926.3(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2012813
_cod_database_fobs_code          2012813
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'
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_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 19 1
-1 -18 -3
1 6 -7
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
N2 C1 C6 107.47(14) n
N2 C1 C16 114.43(13) n
C6 C1 C16 110.60(15) n
N2 C1 C5 101.23(14) n
C6 C1 C5 108.51(16) n
C16 C1 C5 114.01(14) n
C3 N2 C9 122.07(14) n
C3 N2 C1 111.56(13) n
C9 N2 C1 122.47(13) n
O8 C3 N2 124.20(17) n
O8 C3 C4 127.19(17) n
N2 C3 C4 108.60(15) n
C3 C4 C5 104.08(15) n
C3 C4 H4B 107.4(12) n
C5 C4 H4B 109.9(12) n
C3 C4 H4A 112.9(14) n
C5 C4 H4A 113.6(14) n
H4B C4 H4A 108.8(19) n
C4 C5 C1 103.75(15) n
C4 C5 H5B 115.1(12) n
C1 C5 H5B 109.5(12) n
C4 C5 H5A 110.3(13) n
C1 C5 H5A 107.5(12) n
H5B C5 H5A 110.3(17) n
N7 C6 C1 175.1(2) n
C14 C9 C10 119.60(18) n
C14 C9 N2 119.96(16) n
C10 C9 N2 120.41(17) n
C9 C10 C11 119.7(2) n
C9 C10 H10 117.8(12) n
C11 C10 H10 122.4(12) n
C12 C11 C10 121.3(2) n
C12 C11 H11 120.2(15) n
C10 C11 H11 118.5(15) n
C11 C12 C13 118.2(2) n
C11 C12 C15 121.0(2) n
C13 C12 C15 120.8(2) n
C12 C13 C14 121.1(2) n
C12 C13 H13 119.1(14) n
C14 C13 H13 119.7(14) n
C9 C14 C13 120.1(2) n
C9 C14 H14 118.9(13) n
C13 C14 H14 120.9(13) n
C12 C15 H15A 109.5 n
C12 C15 H15B 109.5 n
H15A C15 H15B 109.5 n
C12 C15 H15C 109.5 n
H15A C15 H15C 109.5 n
H15B C15 H15C 109.5 n
C17 C16 C21 117.88(16) n
C17 C16 C1 122.35(15) n
C21 C16 C1 119.67(15) n
C16 C17 C18 121.81(17) n
C16 C17 H17 121.1(13) n
C18 C17 H17 117.1(13) n
C19 C18 C17 119.61(18) n
C19 C18 H18 119.9(14) n
C17 C18 H18 120.4(14) n
O22 C19 C18 125.05(17) n
O22 C19 C20 115.57(16) n
C18 C19 C20 119.37(16) n
C21 C20 C19 120.14(16) n
C21 C20 H20 123.3(12) n
C19 C20 H20 116.5(12) n
C20 C21 C16 121.17(17) n
C20 C21 H21 121.3(11) n
C16 C21 H21 117.5(11) n
C19 O22 C23 119.09(16) n
O22 C23 C25 110.1(2) n
O22 C23 C24 105.2(2) n
C25 C23 C24 113.0(2) n
O22 C23 H23 106.5(15) n
C25 C23 H23 113.3(15) n
C24 C23 H23 108.2(14) n
C23 C24 H24A 109.5 n
C23 C24 H24D 109.5 n
H24A C24 H24D 109.5 n
C23 C24 H24B 109.5 n
H24A C24 H24B 109.5 n
H24D C24 H24B 109.5 n
C23 C25 H25D 109.5 n
C23 C25 H25A 109.5 n
H25D C25 H25A 109.5 n
C23 C25 H25B 109.5 n
H25D C25 H25B 109.5 n
H25A C25 H25B 109.5 n
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
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 N2 C3 -87.82(18) n
C16 C1 N2 C3 148.95(15) n
C5 C1 N2 C3 25.88(18) n
C6 C1 N2 C9 70.32(19) n
C16 C1 N2 C9 -52.9(2) n
C5 C1 N2 C9 -175.99(15) n
C9 N2 C3 O8 11.7(3) n
C1 N2 C3 O8 169.96(18) n
C9 N2 C3 C4 -166.93(16) n
C1 N2 C3 C4 -8.7(2) n
O8 C3 C4 C5 168.5(2) n
N2 C3 C4 C5 -12.9(2) n
C3 C4 C5 C1 28.0(2) n
N2 C1 C5 C4 -32.24(19) n
C6 C1 C5 C4 80.66(19) n
C16 C1 C5 C4 -155.61(16) n
C3 N2 C9 C14 -113.3(2) n
C1 N2 C9 C14 90.8(2) n
C3 N2 C9 C10 65.0(2) n
C1 N2 C9 C10 -90.9(2) n
C14 C9 C10 C11 -0.6(3) n
N2 C9 C10 C11 -178.88(19) n
C9 C10 C11 C12 -0.4(4) n
C10 C11 C12 C13 0.8(4) n
C10 C11 C12 C15 -180.0(2) n
C11 C12 C13 C14 -0.3(4) n
C15 C12 C13 C14 -179.5(2) n
C10 C9 C14 C13 1.1(3) n
N2 C9 C14 C13 179.42(18) n
C12 C13 C14 C9 -0.7(4) n
N2 C1 C16 C17 121.97(18) n
C6 C1 C16 C17 0.4(2) n
C5 C1 C16 C17 -122.15(19) n
N2 C1 C16 C21 -61.8(2) n
C6 C1 C16 C21 176.72(15) n
C5 C1 C16 C21 54.1(2) n
C21 C16 C17 C18 -1.0(3) n
C1 C16 C17 C18 175.34(17) n
C16 C17 C18 C19 0.1(3) n
C17 C18 C19 O22 179.94(18) n
C17 C18 C19 C20 0.7(3) n
O22 C19 C20 C21 -179.90(15) n
C18 C19 C20 C21 -0.6(3) n
C19 C20 C21 C16 -0.3(3) n
C17 C16 C21 C20 1.1(2) n
C1 C16 C21 C20 -175.34(15) n
C18 C19 O22 C23 9.3(3) n
C20 C19 O22 C23 -171.41(18) n
C19 O22 C23 C25 75.7(2) n
C19 O22 C23 C24 -162.24(18) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21134822
