#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/58/2225879.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_2225879
loop_
_publ_author_name
'Lamb, Claude N.'
'Assefa, Zerihun'
'Sykora, Richard E.'
_publ_section_title
;
 Ethyl 5-oxo-2,3-diphenylcyclopentane-1-carboxylate
;
_journal_coeditor_code           HG2655
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1183
_journal_paper_doi               10.1107/S1600536810014728
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H20 O3'
_chemical_formula_moiety         'C20 H20 O3'
_chemical_formula_sum            'C20 H20 O3'
_chemical_formula_weight         308.36
_chemical_name_systematic
;
Ethyl 5-oxo-2,3-diphenylcyclopentane-1-carboxylate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.389(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.4961(13)
_cell_length_b                   7.4008(2)
_cell_length_c                   18.7063(10)
_cell_measurement_pressure       101.3
_cell_measurement_reflns_used    2093
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.2865
_cell_measurement_theta_min      2.9703
_cell_volume                     3439.0(3)
_computing_cell_refinement
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis Pro (Oxford Diffraction, 2009)
;
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.0514
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       'ω scans'
_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  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6900
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
[CrysAlis Pro (Oxford Diffraction, 2009) and
Clark & Reid (1995)]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.132
_refine_ls_extinction_coef       0.0016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.830
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.830
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0404
_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)+(0.0618P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                1509
_reflns_number_total             3025
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2655.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2225879
_cod_database_fobs_code          2225879
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.07043(8) 0.5517(3) 0.12865(12) 0.0674(6) Uani d . 1 . .
C C2 0.07109(7) 0.4093(2) 0.07003(11) 0.0555(5) Uani d . 1 . .
H H2 0.0459 0.4470 0.0167 0.067 Uiso calc R 1 . .
C C3 0.12801(6) 0.4166(2) 0.07539(10) 0.0512(5) Uani d . 1 . .
H H3 0.1511 0.3419 0.1205 0.061 Uiso calc R 1 . .
C C4 0.14455(7) 0.6168(2) 0.09701(11) 0.0556(5) Uani d . 1 . .
H H4 0.1260 0.6894 0.0491 0.067 Uiso calc R 1 . .
C C5 0.12035(7) 0.6635(2) 0.15433(12) 0.0679(6) Uani d . 1 . .
H H5A 0.1453 0.6342 0.2082 0.082 Uiso calc R 1 . .
H H5B 0.1117 0.7912 0.1515 0.082 Uiso calc R 1 . .
C C6 0.05346(8) 0.2295(3) 0.08650(12) 0.0648(6) Uani d . 1 . .
C C7 -0.02207(10) 0.0601(3) 0.0812(2) 0.1136(10) Uani d . 1 . .
H H7A -0.0551 0.0236 0.0369 0.136 Uiso calc R 1 . .
H H7B 0.0034 -0.0389 0.0935 0.136 Uiso calc R 1 . .
C C8 -0.0323(2) 0.0926(5) 0.1442(3) 0.248(3) Uani d . 1 . .
H H8A 0.0011 0.1017 0.1909 0.371 Uiso calc R 1 . .
H H8B -0.0533 -0.0047 0.1503 0.371 Uiso calc R 1 . .
H H8C -0.0519 0.2038 0.1364 0.371 Uiso calc R 1 . .
C C9 0.13429(7) 0.3507(2) 0.00345(11) 0.0555(5) Uani d . 1 . .
C C10 0.10049(8) 0.4082(3) -0.07179(12) 0.0702(6) Uani d . 1 . .
H H10 0.0728 0.4883 -0.0787 0.084 Uiso calc R 1 . .
C C11 0.10716(10) 0.3488(3) -0.13712(14) 0.0880(7) Uani d . 1 . .
H H11 0.0839 0.3884 -0.1874 0.106 Uiso calc R 1 . .
C C12 0.14780(12) 0.2323(3) -0.12798(17) 0.0965(8) Uani d . 1 . .
H H12 0.1523 0.1922 -0.1719 0.116 Uiso calc R 1 . .
C C13 0.18164(11) 0.1751(3) -0.05443(18) 0.0934(7) Uani d . 1 . .
H H13 0.2095 0.0963 -0.0481 0.112 Uiso calc R 1 . .
C C14 0.17513(8) 0.2328(3) 0.01133(14) 0.0759(6) Uani d . 1 . .
H H14 0.1985 0.1916 0.0613 0.091 Uiso calc R 1 . .
C C15 0.20420(7) 0.6534(2) 0.12792(11) 0.0533(5) Uani d . 1 . .
C C16 0.22364(8) 0.7672(3) 0.08826(13) 0.0715(6) Uani d . 1 . .
H H16 0.1998 0.8202 0.0412 0.086 Uiso calc R 1 . .
C C17 0.27797(10) 0.8043(3) 0.11702(16) 0.0886(7) Uani d . 1 . .
H H17 0.2904 0.8824 0.0895 0.106 Uiso calc R 1 . .
C C18 0.31355(9) 0.7261(3) 0.18599(16) 0.0832(7) Uani d . 1 . .
H H18 0.3502 0.7507 0.2055 0.100 Uiso calc R 1 . .
C C19 0.29501(8) 0.6119(3) 0.22596(13) 0.0757(6) Uani d . 1 . .
H H19 0.3191 0.5579 0.2726 0.091 Uiso calc R 1 . .
C C20 0.24114(8) 0.5764(2) 0.19776(12) 0.0655(6) Uani d . 1 . .
H H20 0.2290 0.4993 0.2259 0.079 Uiso calc R 1 . .
O O1 0.03553(6) 0.5692(2) 0.15029(11) 0.1100(6) Uani d . 1 . .
O O2 0.08328(6) 0.10985(18) 0.12097(10) 0.1022(6) Uani d . 1 . .
O O3 -0.00002(5) 0.21897(16) 0.05868(9) 0.0815(5) Uani 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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C5 . . 126.14(19) ?
O1 C1 C2 . . 125.13(18) ?
C5 C1 C2 . . 108.73(17) ?
C6 C2 C3 . . 115.64(15) ?
C6 C2 C1 . . 111.23(16) ?
C3 C2 C1 . . 104.83(14) ?
C6 C2 H2 . . 108.3 ?
C3 C2 H2 . . 108.3 ?
C1 C2 H2 . . 108.3 ?
C9 C3 C2 . . 115.86(14) ?
C9 C3 C4 . . 114.09(15) ?
C2 C3 C4 . . 103.23(13) ?
C9 C3 H3 . . 107.7 ?
C2 C3 H3 . . 107.7 ?
C4 C3 H3 . . 107.7 ?
C15 C4 C5 . . 114.81(15) ?
C15 C4 C3 . . 114.83(13) ?
C5 C4 C3 . . 103.44(14) ?
C15 C4 H4 . . 107.8 ?
C5 C4 H4 . . 107.8 ?
C3 C4 H4 . . 107.8 ?
C1 C5 C4 . . 105.42(16) ?
C1 C5 H5A . . 110.7 ?
C4 C5 H5A . . 110.7 ?
C1 C5 H5B . . 110.7 ?
C4 C5 H5B . . 110.7 ?
H5A C5 H5B . . 108.8 ?
O2 C6 O3 . . 123.72(18) ?
O2 C6 C2 . . 124.42(17) ?
O3 C6 C2 . . 111.86(17) ?
C8 C7 O3 . . 112.1(2) ?
C8 C7 H7A . . 109.2 ?
O3 C7 H7A . . 109.2 ?
C8 C7 H7B . . 109.2 ?
O3 C7 H7B . . 109.2 ?
H7A C7 H7B . . 107.9 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C14 C9 C10 . . 117.8(2) ?
C14 C9 C3 . . 120.56(17) ?
C10 C9 C3 . . 121.67(17) ?
C9 C10 C11 . . 121.1(2) ?
C9 C10 H10 . . 119.5 ?
C11 C10 H10 . . 119.5 ?
C12 C11 C10 . . 120.2(2) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C13 C12 C11 . . 119.6(2) ?
C13 C12 H12 . . 120.2 ?
C11 C12 H12 . . 120.2 ?
C12 C13 C14 . . 120.8(2) ?
C12 C13 H13 . . 119.6 ?
C14 C13 H13 . . 119.6 ?
C9 C14 C13 . . 120.6(2) ?
C9 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
C16 C15 C20 . . 117.59(17) ?
C16 C15 C4 . . 120.89(16) ?
C20 C15 C4 . . 121.51(17) ?
C15 C16 C17 . . 121.2(2) ?
C15 C16 H16 . . 119.4 ?
C17 C16 H16 . . 119.4 ?
C18 C17 C16 . . 120.0(2) ?
C18 C17 H17 . . 120.0 ?
C16 C17 H17 . . 120.0 ?
C19 C18 C17 . . 119.6(2) ?
C19 C18 H18 . . 120.2 ?
C17 C18 H18 . . 120.2 ?
C18 C19 C20 . . 120.3(2) ?
C18 C19 H19 . . 119.8 ?
C20 C19 H19 . . 119.8 ?
C19 C20 C15 . . 121.2(2) ?
C19 C20 H20 . . 119.4 ?
C15 C20 H20 . . 119.4 ?
C6 O3 C7 . . 117.20(17) ?
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 O1 . 1.198(2) ?
C1 C5 . 1.495(2) ?
C1 C2 . 1.527(3) ?
C2 C6 . 1.493(2) ?
C2 C3 . 1.526(2) ?
C2 H2 . 0.9800 ?
C3 C9 . 1.509(2) ?
C3 C4 . 1.552(2) ?
C3 H3 . 0.9800 ?
C4 C15 . 1.511(2) ?
C4 C5 . 1.525(3) ?
C4 H4 . 0.9800 ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 O2 . 1.191(2) ?
C6 O3 . 1.335(2) ?
C7 C8 . 1.344(4) ?
C7 O3 . 1.465(2) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 C14 . 1.379(2) ?
C9 C10 . 1.380(3) ?
C10 C11 . 1.383(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.363(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.356(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.384(3) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 C16 . 1.373(3) ?
C15 C20 . 1.388(2) ?
C16 C17 . 1.381(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.369(3) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.364(3) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.368(3) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 218494
2 PubChem 139078800
