#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/71/1507146.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_1507146
loop_
_publ_author_name
'Yuan, Feng-Quan'
'Han, Fu-She'
_publ_section_title
;
 Synthesis of Densely Substituted α,β,γ,δ-Dienones via the
 Pd(II)-Catalyzed Allylation, H-Migration, and Aerobic Oxidative
 δ-Hydride Elimination Cascade.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1218
_journal_page_last               1221
_journal_paper_doi               10.1021/ol203444g
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C20 H18 O2'
_chemical_formula_weight         290.34
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 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                   9.9470(11)
_cell_length_b                   20.244(2)
_cell_length_c                   7.9602(9)
_cell_measurement_reflns_used    1681
_cell_measurement_temperature    188(2)
_cell_measurement_theta_max      20.35
_cell_measurement_theta_min      2.75
_cell_volume                     1602.9(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      188(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX CCD area detector'
_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  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8892
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_correction_T_min  0.9760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2832
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.972
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0557P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0984
_reflns_number_gt                2352
_reflns_number_total             2832
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol203444g_si_002.cif
_cod_data_source_block           v200
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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 
;
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               1507146
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'
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
C1 C 0.38381(19) 0.88919(11) -0.0270(3) 0.0321(5) Uani 1 1 d .
C2 C 0.3742(2) 0.94325(11) 0.0814(3) 0.0381(5) Uani 1 1 d .
H2 H 0.3828 0.9371 0.1992 0.046 Uiso 1 1 calc R
C3 C 0.3520(2) 1.00586(12) 0.0169(3) 0.0428(6) Uani 1 1 d .
H3 H 0.3466 1.0424 0.0913 0.051 Uiso 1 1 calc R
C4 C 0.3378(2) 1.01605(12) -0.1535(3) 0.0421(6) Uani 1 1 d .
H4 H 0.3232 1.0593 -0.1961 0.051 Uiso 1 1 calc R
C5 C 0.3449(2) 0.96284(12) -0.2615(3) 0.0423(6) Uani 1 1 d .
H5 H 0.3339 0.9693 -0.3789 0.051 Uiso 1 1 calc R
C6 C 0.3680(2) 0.90007(12) -0.1987(3) 0.0371(6) Uani 1 1 d .
H6 H 0.3733 0.8638 -0.2741 0.045 Uiso 1 1 calc R
C7 C 0.4125(2) 0.82181(10) 0.0323(3) 0.0325(5) Uani 1 1 d .
H7 H 0.4067 0.7875 -0.0489 0.039 Uiso 1 1 calc R
C8 C 0.44576(19) 0.80383(10) 0.1883(3) 0.0337(5) Uani 1 1 d .
H8 H 0.4463 0.8367 0.2735 0.040 Uiso 1 1 calc R
C9 C 0.48141(18) 0.73601(10) 0.2351(3) 0.0304(5) Uani 1 1 d .
C10 C 0.4414(2) 0.68180(10) 0.1177(3) 0.0297(5) Uani 1 1 d .
C11 C 0.5393(2) 0.64153(11) 0.0464(3) 0.0366(5) Uani 1 1 d .
H11 H 0.6315 0.6503 0.0681 0.044 Uiso 1 1 calc R
C12 C 0.5045(2) 0.58909(11) -0.0551(3) 0.0437(6) Uani 1 1 d .
H12 H 0.5724 0.5617 -0.1020 0.052 Uiso 1 1 calc R
C13 C 0.3711(2) 0.57643(12) -0.0886(3) 0.0446(6) Uani 1 1 d .
H13 H 0.3468 0.5399 -0.1570 0.053 Uiso 1 1 calc R
C14 C 0.2732(2) 0.61681(11) -0.0227(3) 0.0414(6) Uani 1 1 d .
H14 H 0.1813 0.6084 -0.0474 0.050 Uiso 1 1 calc R
C15 C 0.3074(2) 0.66961(11) 0.0792(3) 0.0353(5) Uani 1 1 d .
H15 H 0.2392 0.6976 0.1230 0.042 Uiso 1 1 calc R
C16 C 0.5526(2) 0.72071(10) 0.3758(3) 0.0330(5) Uani 1 1 d .
C17 C 0.5855(2) 0.64977(11) 0.4205(3) 0.0362(5) Uani 1 1 d .
C18 C 0.4734(3) 0.60189(12) 0.4518(4) 0.0569(7) Uani 1 1 d .
H18A H 0.4428 0.5834 0.3445 0.085 Uiso 1 1 calc R
H18B H 0.3986 0.6248 0.5068 0.085 Uiso 1 1 calc R
H18C H 0.5056 0.5661 0.5243 0.085 Uiso 1 1 calc R
C19 C 0.6086(2) 0.77060(12) 0.4950(3) 0.0401(6) Uani 1 1 d .
C20 C 0.6283(3) 0.74959(14) 0.6735(4) 0.0714(9) Uani 1 1 d .
H20A H 0.7124 0.7247 0.6833 0.107 Uiso 1 1 calc R
H20B H 0.5529 0.7216 0.7084 0.107 Uiso 1 1 calc R
H20C H 0.6325 0.7887 0.7458 0.107 Uiso 1 1 calc R
O1 O 0.70216(16) 0.63430(8) 0.4400(2) 0.0516(5) Uani 1 1 d .
O2 O 0.6358(2) 0.82627(9) 0.4524(2) 0.0641(5) Uani 1 1 d .
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
C6 C1 C2 118.3(2)
C6 C1 C7 118.9(2)
C2 C1 C7 122.8(2)
C3 C2 C1 119.9(2)
C3 C2 H2 120.0
C1 C2 H2 120.0
C4 C3 C2 121.2(2)
C4 C3 H3 119.4
C2 C3 H3 119.4
C5 C4 C3 119.4(2)
C5 C4 H4 120.3
C3 C4 H4 120.3
C4 C5 C6 120.0(2)
C4 C5 H5 120.0
C6 C5 H5 120.0
C5 C6 C1 121.2(2)
C5 C6 H6 119.4
C1 C6 H6 119.4
C8 C7 C1 126.8(2)
C8 C7 H7 116.6
C1 C7 H7 116.6
C7 C8 C9 123.5(2)
C7 C8 H8 118.3
C9 C8 H8 118.3
C16 C9 C8 123.25(19)
C16 C9 C10 119.07(18)
C8 C9 C10 117.63(18)
C15 C10 C11 118.6(2)
C15 C10 C9 121.54(19)
C11 C10 C9 119.90(19)
C12 C11 C10 121.0(2)
C12 C11 H11 119.5
C10 C11 H11 119.5
C13 C12 C11 119.9(2)
C13 C12 H12 120.0
C11 C12 H12 120.0
C12 C13 C14 119.9(2)
C12 C13 H13 120.1
C14 C13 H13 120.1
C13 C14 C15 120.5(2)
C13 C14 H14 119.7
C15 C14 H14 119.7
C14 C15 C10 120.1(2)
C14 C15 H15 119.9
C10 C15 H15 119.9
C9 C16 C19 124.26(19)
C9 C16 C17 121.45(19)
C19 C16 C17 114.25(19)
O1 C17 C18 121.6(2)
O1 C17 C16 118.82(19)
C18 C17 C16 119.43(19)
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
O2 C19 C16 122.4(2)
O2 C19 C20 120.2(2)
C16 C19 C20 117.4(2)
C19 C20 H20A 109.5
C19 C20 H20B 109.5
H20A C20 H20B 109.5
C19 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.393(3)
C1 C2 1.397(3)
C1 C7 1.471(3)
C2 C3 1.385(3)
C2 H2 0.9500
C3 C4 1.379(3)
C3 H3 0.9500
C4 C5 1.380(3)
C4 H4 0.9500
C5 C6 1.385(3)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.336(3)
C7 H7 0.9500
C8 C9 1.466(3)
C8 H8 0.9500
C9 C16 1.360(3)
C9 C10 1.496(3)
C10 C15 1.389(3)
C10 C11 1.391(3)
C11 C12 1.379(3)
C11 H11 0.9500
C12 C13 1.377(3)
C12 H12 0.9500
C13 C14 1.376(3)
C13 H13 0.9500
C14 C15 1.385(3)
C14 H14 0.9500
C15 H15 0.9500
C16 C19 1.493(3)
C16 C17 1.515(3)
C17 O1 1.212(2)
C17 C18 1.498(3)
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
C19 O2 1.208(3)
C19 C20 1.496(4)
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30651784
2 PubChem 101572940
