#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/54/2215498.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_2215498
loop_
_publ_author_name
'Tamazyan, Rafael'
'Matevosyan, Levon'
'Martirosyan, Ashot'
'Gasparyan, Sahak'
'Raymond Schinazi'
_publ_section_title
cis-1-Benzoyl-2-(2-benzyloxy-5-chlorophenyl)-4-chloropyrrolidine-2-carbonitrile
_journal_coeditor_code           HB2520
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4069
_journal_page_last               o4069
_journal_paper_doi               10.1107/S1600536807043875
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C25 H20 Cl2 N2 O2'
_chemical_formula_moiety         'C25 H20 Cl2 N2 O2'
_chemical_formula_sum            'C25 H20 Cl2 N2 O2'
_chemical_formula_weight         451.33
_chemical_melting_point          470
_chemical_name_common
1-benzoyl-2-(2-benzyloxyphenyl)-2-pyrrolidinecarbonitrile
_chemical_name_systematic
;
cis-1-Benzoyl-2-(2-benzyloxy-5-chlorophenyl)-4-
chloropyrrolidine-2-carbonitrile
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                72.12(3)
_cell_angle_beta                 85.82(3)
_cell_angle_gamma                63.71(3)
_cell_formula_units_Z            2
_cell_length_a                   9.803(2)
_cell_length_b                   10.653(2)
_cell_length_c                   12.364(3)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19
_cell_measurement_theta_min      8
_cell_volume                     1098.7(5)
_computing_cell_refinement       'CAD-4 (Enraf--Nonius, 1988)'
_computing_data_collection       'CAD-4 (Enraf--Nonius, 1988)'
_computing_data_reduction        'HELENA (Meetsma & Spek, 2000)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       θ/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  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5515
_diffrn_reflns_theta_full        27.98
_diffrn_reflns_theta_max         27.98
_diffrn_reflns_theta_min         1.74
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  180
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.504
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         5275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0610P)²+0.5189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1307
_reflns_number_gt                4051
_reflns_number_total             5275
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2520.cif
_cod_data_source_block           I
_cod_database_code               2215498
_cod_database_fobs_code          2215498
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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_occupancy
Cl Cl31 -0.02327(7) 1.42050(6) 0.34471(6) 0.05911(19) Uani d 1
Cl Cl30 0.60429(8) 0.90398(7) 0.89834(6) 0.06254(19) Uani d 1
C C1 0.33489(19) 1.00696(18) 0.69407(15) 0.0295(3) Uani d 1
N N2 0.32236(16) 0.88563(15) 0.78477(12) 0.0293(3) Uani d 1
C C3 0.4723(2) 0.7608(2) 0.82939(19) 0.0362(4) Uani d 1
C C4 0.5823(2) 0.8276(2) 0.79414(19) 0.0415(4) Uani d 1
C C5 0.5093(2) 0.9450(2) 0.68135(18) 0.0383(4) Uani d 1
C C6 0.24513(19) 1.05051(19) 0.58226(15) 0.0304(4) Uani d 1
C C7 0.1567(2) 1.1973(2) 0.52203(17) 0.0344(4) Uani d 1
C C8 0.0817(2) 1.2353(2) 0.41798(17) 0.0384(4) Uani d 1
C C9 0.0887(2) 1.1298(2) 0.37306(19) 0.0431(5) Uani d 1
C C10 0.1752(2) 0.9826(2) 0.43219(18) 0.0398(4) Uani d 1
C C11 0.2554(2) 0.9424(2) 0.53481(16) 0.0341(4) Uani d 1
O O12 0.34923(17) 0.80024(14) 0.59518(12) 0.0422(3) Uani d 1
C C13 0.3730(3) 0.6863(2) 0.5458(2) 0.0463(5) Uani d 1
C C14 0.4946(2) 0.5453(2) 0.62109(19) 0.0414(5) Uani d 1
C C15 0.4567(2) 0.4404(2) 0.6931(2) 0.0433(5) Uani d 1
C C16 0.5679(3) 0.3085(3) 0.7622(2) 0.0524(6) Uani d 1
C C17 0.7178(3) 0.2813(3) 0.7578(3) 0.0599(7) Uani d 1
C C18 0.7579(3) 0.3847(3) 0.6866(3) 0.0650(8) Uani d 1
C C19 0.6469(3) 0.5170(3) 0.6178(2) 0.0533(6) Uani d 1
C C20 0.2847(2) 1.1372(2) 0.73542(16) 0.0350(4) Uani d 1
N N21 0.2518(2) 1.23812(19) 0.76384(17) 0.0481(4) Uani d 1
C C22 0.1827(2) 0.90207(19) 0.82009(15) 0.0316(4) Uani d 1
O O23 0.07083(15) 1.02139(14) 0.78492(13) 0.0446(4) Uani d 1
C C24 0.1688(2) 0.7713(2) 0.89974(15) 0.0325(4) Uani d 1
C C25 0.0677(3) 0.7920(3) 0.9841(2) 0.0472(5) Uani d 1
C C26 0.0475(3) 0.6741(3) 1.0559(2) 0.0579(6) Uani d 1
C C27 0.1249(3) 0.5373(3) 1.0421(2) 0.0537(6) Uani d 1
C C28 0.2208(3) 0.5165(2) 0.9567(2) 0.0509(5) Uani d 1
C C29 0.2441(2) 0.6330(2) 0.88615(19) 0.0410(4) Uani d 1
H H1 0.356(3) 0.458(2) 0.6938(19) 0.038(6) Uiso d 1
H H2 0.143(3) 1.273(3) 0.555(2) 0.045(6) Uiso d 1
H H3 0.497(2) 0.687(2) 0.7912(17) 0.028(5) Uiso d 1
H H4 0.544(2) 1.021(3) 0.6607(19) 0.039(6) Uiso d 1
H H5 0.679(3) 0.757(3) 0.787(2) 0.049(6) Uiso d 1
H H6 0.474(3) 0.721(2) 0.907(2) 0.040(6) Uiso d 1
H H7 0.533(2) 0.896(2) 0.6244(19) 0.037(5) Uiso d 1
H H8 0.011(3) 0.888(3) 0.984(2) 0.058(7) Uiso d 1
H H9 0.668(3) 0.589(3) 0.566(2) 0.063(8) Uiso d 1
H H10 0.305(3) 0.619(2) 0.8272(19) 0.037(6) Uiso d 1
H H11 0.104(3) 0.461(3) 1.088(2) 0.068(8) Uiso d 1
H H12 0.793(3) 0.196(3) 0.804(3) 0.068(8) Uiso d 1
H H13 0.270(3) 0.682(3) 0.539(2) 0.049(6) Uiso d 1
H H14 0.182(3) 0.916(3) 0.403(2) 0.048(7) Uiso d 1
H H15 0.266(3) 0.425(3) 0.942(2) 0.068(8) Uiso d 1
H H16 0.542(3) 0.239(3) 0.815(2) 0.063(8) Uiso d 1
H H17 0.407(3) 0.715(3) 0.469(2) 0.052(7) Uiso d 1
H H18 -0.018(3) 0.690(3) 1.108(3) 0.071(9) Uiso d 1
H H19 0.035(3) 1.158(3) 0.306(2) 0.051(7) Uiso d 1
H H20 0.851(4) 0.373(3) 0.681(3) 0.077(9) Uiso d 1
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 C20 109.20(14) n
N2 C1 C6 114.02(14) n
C20 C1 C6 109.83(14) n
N2 C1 C5 102.64(14) n
C20 C1 C5 108.75(16) n
C6 C1 C5 112.09(15) n
C22 N2 C3 128.35(15) n
C22 N2 C1 119.22(14) n
C3 N2 C1 112.36(14) n
N2 C3 C4 103.58(15) n
N2 C3 H3 110.8(12) n
C4 C3 H3 107.1(12) n
N2 C3 H6 110.3(14) n
C4 C3 H6 113.4(14) n
H3 C3 H6 111.4(18) n
C3 C4 C5 103.64(16) n
C3 C4 Cl30 111.10(16) n
C5 C4 Cl30 111.88(15) n
C3 C4 H5 111.3(15) n
C5 C4 H5 112.2(15) n
Cl30 C4 H5 106.8(15) n
C4 C5 C1 105.15(16) n
C4 C5 H4 113.8(13) n
C1 C5 H4 112.5(13) n
C4 C5 H7 106.9(13) n
C1 C5 H7 108.0(13) n
H4 C5 H7 110.1(19) n
C7 C6 C11 118.25(17) n
C7 C6 C1 121.17(16) n
C11 C6 C1 120.52(15) n
C8 C7 C6 120.49(18) n
C8 C7 H2 120.0(14) n
C6 C7 H2 119.5(14) n
C9 C8 C7 121.24(18) n
C9 C8 Cl31 120.22(16) n
C7 C8 Cl31 118.54(16) n
C8 C9 C10 119.2(2) n
C8 C9 H19 119.1(15) n
C10 C9 H19 121.6(16) n
C9 C10 C11 120.3(2) n
C9 C10 H14 119.2(16) n
C11 C10 H14 120.4(16) n
O12 C11 C10 123.82(17) n
O12 C11 C6 115.78(16) n
C10 C11 C6 120.39(17) n
C11 O12 C13 117.91(16) n
O12 C13 C14 106.96(17) n
O12 C13 H13 109.4(13) n
C14 C13 H13 113.1(13) n
O12 C13 H17 106.6(14) n
C14 C13 H17 111.2(14) n
H13 C13 H17 109(2) n
C15 C14 C19 118.7(2) n
C15 C14 C13 120.3(2) n
C19 C14 C13 121.0(2) n
C14 C15 C16 121.2(2) n
C14 C15 H1 119.0(14) n
C16 C15 H1 119.9(14) n
C17 C16 C15 119.7(3) n
C17 C16 H16 118.8(17) n
C15 C16 H16 121.5(17) n
C16 C17 C18 120.0(2) n
C16 C17 H12 121.4(18) n
C18 C17 H12 118.6(18) n
C17 C18 C19 120.4(2) n
C17 C18 H20 124(2) n
C19 C18 H20 116(2) n
C14 C19 C18 120.1(3) n
C14 C19 H9 115.8(17) n
C18 C19 H9 124.1(17) n
N21 C20 C1 176.5(2) n
O23 C22 N2 120.07(17) n
O23 C22 C24 121.38(17) n
N2 C22 C24 118.54(15) n
C29 C24 C25 118.98(19) n
C29 C24 C22 122.17(17) n
C25 C24 C22 118.63(17) n
C24 C25 C26 120.0(2) n
C24 C25 H8 115.9(16) n
C26 C25 H8 123.9(16) n
C27 C26 C25 120.2(2) n
C27 C26 H18 121.2(19) n
C25 C26 H18 118.6(19) n
C28 C27 C26 120.5(2) n
C28 C27 H11 120.9(18) n
C26 C27 H11 118.4(18) n
C27 C28 C29 119.7(2) n
C27 C28 H15 120.7(18) n
C29 C28 H15 119.3(18) n
C28 C29 C24 120.6(2) n
C28 C29 H10 118.8(14) n
C24 C29 H10 120.4(14) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl31 C8 1.735(2) n
Cl30 C4 1.791(2) n
C1 N2 1.474(2) n
C1 C20 1.491(2) n
C1 C6 1.524(3) n
C1 C5 1.552(2) n
N2 C22 1.358(2) n
N2 C3 1.473(2) n
C3 C4 1.510(3) n
C3 H3 0.97(2) n
C3 H6 0.92(2) n
C4 C5 1.518(3) n
C4 H5 0.94(2) n
C5 H4 0.96(2) n
C5 H7 0.96(2) n
C6 C7 1.389(3) n
C6 C11 1.408(3) n
C7 C8 1.383(3) n
C7 H2 0.97(2) n
C8 C9 1.373(3) n
C9 C10 1.387(3) n
C9 H19 0.91(3) n
C10 C11 1.388(3) n
C10 H14 0.87(3) n
C11 O12 1.367(2) n
O12 C13 1.444(2) n
C13 C14 1.503(3) n
C13 H13 1.04(3) n
C13 H17 0.99(3) n
C14 C15 1.374(3) n
C14 C19 1.386(3) n
C15 C16 1.391(3) n
C15 H1 0.92(2) n
C16 C17 1.366(4) n
C16 H16 0.94(3) n
C17 C18 1.371(4) n
C17 H12 0.92(3) n
C18 C19 1.391(4) n
C18 H20 0.86(3) n
C19 H9 0.93(3) n
C20 N21 1.137(3) n
C22 O23 1.226(2) n
C22 C24 1.495(3) n
C24 C29 1.384(3) n
C24 C25 1.384(3) n
C25 C26 1.384(3) n
C25 H8 0.93(3) n
C26 C27 1.372(4) n
C26 H18 0.88(3) n
C27 C28 1.364(4) n
C27 H11 0.93(3) n
C28 C29 1.382(3) n
C28 H15 0.95(3) n
C29 H10 0.91(2) 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
C20 C1 N2 C22 64.0(2) n
C6 C1 N2 C22 -59.3(2) n
C5 C1 N2 C22 179.22(16) n
C20 C1 N2 C3 -113.25(17) n
C6 C1 N2 C3 123.48(16) n
C5 C1 N2 C3 2.02(19) n
C22 N2 C3 C4 -157.32(18) n
C1 N2 C3 C4 19.6(2) n
N2 C3 C4 C5 -33.1(2) n
N2 C3 C4 Cl30 87.23(17) n
C3 C4 C5 C1 35.1(2) n
Cl30 C4 C5 C1 -84.71(17) n
N2 C1 C5 C4 -22.87(19) n
C20 C1 C5 C4 92.73(19) n
C6 C1 C5 C4 -145.63(16) n
N2 C1 C6 C7 135.27(17) n
C20 C1 C6 C7 12.3(2) n
C5 C1 C6 C7 -108.67(19) n
N2 C1 C6 C11 -47.6(2) n
C20 C1 C6 C11 -170.52(16) n
C5 C1 C6 C11 68.5(2) n
C11 C6 C7 C8 -0.3(3) n
C1 C6 C7 C8 176.90(17) n
C6 C7 C8 C9 1.9(3) n
C6 C7 C8 Cl31 -178.36(14) n
C7 C8 C9 C10 -1.3(3) n
Cl31 C8 C9 C10 178.97(16) n
C8 C9 C10 C11 -0.9(3) n
C9 C10 C11 O12 -176.54(19) n
C9 C10 C11 C6 2.5(3) n
C7 C6 C11 O12 177.23(16) n
C1 C6 C11 O12 0.0(2) n
C7 C6 C11 C10 -1.9(3) n
C1 C6 C11 C10 -179.10(17) n
C10 C11 O12 C13 3.8(3) n
C6 C11 O12 C13 -175.28(18) n
C11 O12 C13 C14 172.84(18) n
O12 C13 C14 C15 105.1(2) n
O12 C13 C14 C19 -76.2(3) n
C19 C14 C15 C16 0.4(3) n
C13 C14 C15 C16 179.1(2) n
C14 C15 C16 C17 -0.8(3) n
C15 C16 C17 C18 0.9(4) n
C16 C17 C18 C19 -0.6(4) n
C15 C14 C19 C18 -0.1(3) n
C13 C14 C19 C18 -178.8(2) n
C17 C18 C19 C14 0.2(4) n
C3 N2 C22 O23 169.57(18) n
C1 N2 C22 O23 -7.1(3) n
C3 N2 C22 C24 -11.9(3) n
C1 N2 C22 C24 171.39(15) n
O23 C22 C24 C29 136.3(2) n
N2 C22 C24 C29 -42.2(3) n
O23 C22 C24 C25 -38.3(3) n
N2 C22 C24 C25 143.23(19) n
C29 C24 C25 C26 2.4(3) n
C22 C24 C25 C26 177.2(2) n
C24 C25 C26 C27 -1.5(4) n
C25 C26 C27 C28 -0.9(4) n
C26 C27 C28 C29 2.3(4) n
C27 C28 C29 C24 -1.3(3) n
C25 C24 C29 C28 -1.0(3) n
C22 C24 C29 C28 -175.61(19) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139073136
