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#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/90/7239053.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7239053
loop_
_publ_author_name
'Ramachary, Dhevalapally B.'
'Sakthidevi, Rajasekar'
'Reddy, P. Srinivasa'
_publ_section_title
;
 Direct organocatalytic stereoselective transfer hydrogenation of
 conjugated olefins of steroids
;
_journal_issue                   32
_journal_name_full               'RSC Advances'
_journal_page_first              13497
_journal_paper_doi               10.1039/c3ra41519h
_journal_volume                  3
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_sum            'C19 H28 O2'
_chemical_formula_weight         288.41
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9253(18)
_cell_length_b                   8.4074(17)
_cell_length_c                   25.074(5)
_cell_measurement_reflns_used    1490
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.2903
_cell_measurement_theta_min      2.9113
_cell_volume                     1670.7(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'phi and omega 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  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            4819
_diffrn_reflns_theta_full        26.35
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0588
_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)+(0.0575P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1356
_reflns_number_gt                2166
_reflns_number_total             3097
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra41519h.txt
_cod_data_source_block           test
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7239053
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C12 C 0.5104(3) 0.2607(3) 0.87317(12) 0.0653(8) Uani 1 1 d .
H12A H 0.5590 0.1913 0.8464 0.078 Uiso 1 1 calc R
H12B H 0.5518 0.3675 0.8666 0.078 Uiso 1 1 calc R
O2 O 0.6456(3) 0.0064(2) 1.02626(9) 0.0889(7) Uani 1 1 d .
C13 C 0.5710(3) 0.2066(3) 0.92831(12) 0.0646(8) Uani 1 1 d .
H13A H 0.6932 0.1993 0.9284 0.078 Uiso 1 1 calc R
H13B H 0.5381 0.2846 0.9549 0.078 Uiso 1 1 calc R
C9 C 0.3211(4) 0.1948(4) 0.76725(12) 0.0884(10) Uani 1 1 d .
H9A H 0.2841 0.0890 0.7756 0.133 Uiso 1 1 calc R
H9B H 0.4421 0.1974 0.7659 0.133 Uiso 1 1 calc R
H9C H 0.2762 0.2260 0.7333 0.133 Uiso 1 1 calc R
C10 C 0.3178(3) 0.2602(3) 0.86695(10) 0.0465(6) Uani 1 1 d .
H10 H 0.2745 0.3407 0.8917 0.056 Uiso 1 1 calc R
C11 C 0.2394(3) 0.0995(3) 0.88459(10) 0.0460(6) Uani 1 1 d .
H11 H 0.2775 0.0164 0.8600 0.055 Uiso 1 1 calc R
C5 C 0.0643(3) 0.3169(3) 0.80932(11) 0.0562(7) Uani 1 1 d .
H5 H 0.0307 0.3332 0.7721 0.067 Uiso 1 1 calc R
C15 C 0.3034(3) 0.0598(3) 0.93999(11) 0.0488(6) Uani 1 1 d .
H15 H 0.2739 0.1512 0.9624 0.059 Uiso 1 1 calc R
C14 C 0.4960(3) 0.0460(3) 0.94258(11) 0.0521(6) Uani 1 1 d .
C8 C 0.0487(3) 0.1079(3) 0.88227(12) 0.0583(7) Uani 1 1 d .
H8A H 0.0088 0.1825 0.9089 0.070 Uiso 1 1 calc R
H8B H 0.0022 0.0042 0.8907 0.070 Uiso 1 1 calc R
C4 C -0.0099(4) 0.4548(3) 0.84191(12) 0.0667(8) Uani 1 1 d .
H4A H -0.1286 0.4647 0.8331 0.080 Uiso 1 1 calc R
H4B H -0.0027 0.4275 0.8794 0.080 Uiso 1 1 calc R
C6 C 0.2582(3) 0.3106(3) 0.81060(11) 0.0563(7) Uani 1 1 d .
C7 C -0.0137(3) 0.1596(3) 0.82760(12) 0.0636(8) Uani 1 1 d .
H7A H -0.1355 0.1708 0.8287 0.076 Uiso 1 1 calc R
H7B H 0.0131 0.0775 0.8018 0.076 Uiso 1 1 calc R
C16 C 0.5679(3) -0.0877(3) 0.90714(12) 0.0742(9) Uani 1 1 d .
H16A H 0.6885 -0.0904 0.9106 0.111 Uiso 1 1 calc R
H16B H 0.5385 -0.0678 0.8706 0.111 Uiso 1 1 calc R
H16C H 0.5216 -0.1880 0.9181 0.111 Uiso 1 1 calc R
C17 C 0.2410(3) -0.0872(3) 0.97024(13) 0.0674(8) Uani 1 1 d .
H17A H 0.1264 -0.0724 0.9829 0.081 Uiso 1 1 calc R
H17B H 0.2456 -0.1814 0.9480 0.081 Uiso 1 1 calc R
C1 C 0.0714(5) 0.6121(4) 0.83406(13) 0.0822(10) Uani 1 1 d .
O1 O -0.0080(4) 0.7344(3) 0.83193(12) 0.1284(11) Uani 1 1 d .
C19 C 0.5211(4) -0.0118(3) 0.99938(12) 0.0638(7) Uani 1 1 d .
C3 C 0.3213(4) 0.4763(4) 0.79500(14) 0.0845(10) Uani 1 1 d .
H3A H 0.4437 0.4757 0.7956 0.101 Uiso 1 1 calc R
H3B H 0.2863 0.4981 0.7587 0.101 Uiso 1 1 calc R
C2 C 0.2592(5) 0.6107(3) 0.83054(15) 0.0942(12) Uani 1 1 d .
H2A H 0.3065 0.5983 0.8660 0.113 Uiso 1 1 calc R
H2B H 0.2981 0.7116 0.8163 0.113 Uiso 1 1 calc R
C18 C 0.3641(4) -0.0993(4) 1.01646(14) 0.0825(9) Uani 1 1 d .
H18A H 0.3166 -0.0510 1.0482 0.099 Uiso 1 1 calc R
H18B H 0.3898 -0.2097 1.0241 0.099 Uiso 1 1 calc R
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
C13 C12 C10 113.8(2)
C14 C13 C12 110.7(2)
C12 C10 C6 113.3(2)
C12 C10 C11 111.8(2)
C6 C10 C11 112.1(2)
C8 C11 C15 112.3(2)
C8 C11 C10 110.4(2)
C15 C11 C10 108.59(18)
C7 C5 C4 109.8(2)
C7 C5 C6 111.6(2)
C4 C5 C6 113.4(2)
C11 C15 C17 121.5(2)
C11 C15 C14 112.9(2)
C17 C15 C14 103.9(2)
C19 C14 C13 117.0(2)
C19 C14 C15 101.2(2)
C13 C14 C15 108.2(2)
C19 C14 C16 105.0(2)
C13 C14 C16 111.5(2)
C15 C14 C16 113.5(2)
C11 C8 C7 111.9(2)
C1 C4 C5 115.8(3)
C3 C6 C5 106.9(2)
C3 C6 C9 106.8(3)
C5 C6 C9 109.3(2)
C3 C6 C10 112.5(2)
C5 C6 C10 109.4(2)
C9 C6 C10 111.8(2)
C8 C7 C5 112.7(2)
C18 C17 C15 103.0(2)
O1 C1 C4 122.6(4)
O1 C1 C2 121.6(3)
C4 C1 C2 115.8(3)
O2 C19 C18 125.4(3)
O2 C19 C14 126.3(3)
C18 C19 C14 108.3(2)
C2 C3 C6 114.9(3)
C1 C2 C3 111.3(3)
C19 C18 C17 106.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C12 C13 1.533(4)
C12 C10 1.534(3)
O2 C19 1.204(3)
C13 C14 1.518(3)
C9 C6 1.542(4)
C10 C6 1.549(4)
C10 C11 1.551(3)
C11 C8 1.514(3)
C11 C15 1.516(4)
C5 C7 1.530(4)
C5 C4 1.536(4)
C5 C6 1.538(3)
C15 C17 1.532(3)
C15 C14 1.532(3)
C14 C19 1.518(4)
C14 C16 1.542(3)
C8 C7 1.521(4)
C4 C1 1.484(4)
C6 C3 1.531(4)
C17 C18 1.518(4)
C1 O1 1.207(3)
C1 C2 1.491(4)
C19 C18 1.508(4)
C3 C2 1.521(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 23729585
