#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/16/7151698.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_7151698
loop_
_publ_author_name
'Sada, Mutsumi'
'Nomura, Kenichi'
'Matsubara, Seijiro'
_publ_section_title
;
 A tandem reaction of organozinc reagent prepared from
 palladium-catalyzed umpolung method: diastereoselective formation of
 cyclohexene derivatives bearing three adjacent stereocenters.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1389
_journal_page_last               1393
_journal_paper_doi               10.1039/C0OB00806K
_journal_volume                  9
_journal_year                    2011
_chemical_formula_sum            'C22 H22 O4'
_chemical_formula_weight         350.40
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                81.280(2)
_cell_angle_beta                 83.245(2)
_cell_angle_gamma                75.899(2)
_cell_formula_units_Z            2
_cell_length_a                   6.0102(6)
_cell_length_b                   10.0194(9)
_cell_length_c                   15.9053(15)
_cell_measurement_temperature    293(2)
_cell_volume                     914.94(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  '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  0.0150
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5637
_diffrn_reflns_theta_full        27.04
_diffrn_reflns_theta_max         27.04
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_crystal_size_max          2
_exptl_crystal_size_mid          2
_exptl_crystal_size_min          1
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.823
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.823
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1829
_refine_ls_wR_factor_ref         0.1990
_reflns_number_gt                3095
_reflns_number_total             3892
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0OB00806K.TXT
_cod_data_source_block           15nm
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151698
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.30388(17) 0.58955(11) 0.31456(8) 0.0588(3) Uani 1 1 d . . .
H4 H 0.2338 0.5334 0.3051 0.088 Uiso 1 1 calc R . .
O3 O 0.84363(19) 0.11228(10) 0.38749(7) 0.0574(3) Uani 1 1 d . . .
O1 O 0.28016(18) 0.34503(12) 0.26119(8) 0.0633(3) Uani 1 1 d . . .
C1 C 0.6233(2) 0.38503(12) 0.30280(8) 0.0385(3) Uani 1 1 d . . .
H1 H 0.7863 0.3592 0.2822 0.046 Uiso 1 1 calc R . .
C2 C 0.4898(2) 0.31435(13) 0.25506(8) 0.0427(3) Uani 1 1 d . . .
C3 C 0.5854(2) 0.59440(13) 0.19115(9) 0.0457(3) Uani 1 1 d . . .
C4 C 0.6161(2) 0.20136(13) 0.20460(8) 0.0433(3) Uani 1 1 d . . .
C5 C 0.5415(2) 0.54578(13) 0.28588(9) 0.0436(3) Uani 1 1 d . . .
C6 C 0.6015(2) 0.33830(15) 0.39964(8) 0.0474(4) Uani 1 1 d . . .
H6 H 0.4476 0.3849 0.4218 0.057 Uiso 1 1 calc R . .
C7 C 0.8383(3) 0.19282(16) 0.16719(9) 0.0530(4) Uani 1 1 d . . .
H7 H 0.9161 0.2599 0.1734 0.064 Uiso 1 1 calc R . .
C8 C 0.8078(3) 0.57721(16) 0.15351(10) 0.0543(4) Uani 1 1 d . . .
H8 H 0.9302 0.5376 0.1868 0.065 Uiso 1 1 calc R . .
C9 C 0.6734(3) 0.60883(15) 0.33914(9) 0.0509(4) Uani 1 1 d . . .
H9 H 0.6815 0.7009 0.3234 0.061 Uiso 1 1 calc R . .
C10 C 0.6236(3) 0.18390(16) 0.42350(10) 0.0555(4) Uani 1 1 d . . .
H10A H 0.6124 0.1612 0.4851 0.067 Uiso 1 1 calc R . .
H10B H 0.5006 0.1558 0.4015 0.067 Uiso 1 1 calc R . .
C11 C 0.7756(3) 0.39285(17) 0.43983(10) 0.0565(4) Uani 1 1 d . . .
H11A H 0.7394 0.3854 0.5012 0.068 Uiso 1 1 calc R . .
H11B H 0.9283 0.3353 0.4288 0.068 Uiso 1 1 calc R . .
C12 C 0.7763(3) 0.54013(17) 0.40617(10) 0.0548(4) Uani 1 1 d . . .
H12 H 0.8551 0.5863 0.4347 0.066 Uiso 1 1 calc R . .
C13 C 0.4069(3) 0.65582(18) 0.14048(12) 0.0659(5) Uani 1 1 d . . .
H13 H 0.2556 0.6706 0.1645 0.079 Uiso 1 1 calc R . .
C14 C 0.5039(3) 0.09949(16) 0.19502(11) 0.0611(4) Uani 1 1 d . . .
H14 H 0.3536 0.1044 0.2188 0.073 Uiso 1 1 calc R . .
C15 C 0.8353(4) -0.0158(2) 0.11302(12) 0.0726(5) Uani 1 1 d . . .
H15 H 0.9091 -0.0889 0.0827 0.087 Uiso 1 1 calc R . .
C16 C 0.6158(4) -0.00962(18) 0.15001(14) 0.0769(6) Uani 1 1 d . . .
H16 H 0.5415 -0.0789 0.1449 0.092 Uiso 1 1 calc R . .
C17 C 0.9455(3) 0.08528(19) 0.12065(11) 0.0668(5) Uani 1 1 d . . .
H17 H 1.0932 0.0819 0.0945 0.080 Uiso 1 1 calc R . .
C18 C 0.8845(4) -0.02461(17) 0.39337(11) 0.0710(5) Uani 1 1 d . . .
C19 C 0.8522(3) 0.61759(19) 0.06764(11) 0.0668(5) Uani 1 1 d . . .
H19 H 1.0033 0.6061 0.0437 0.080 Uiso 1 1 calc R . .
C20 C 0.4524(4) 0.6953(2) 0.05426(14) 0.0825(6) Uani 1 1 d . . .
H20 H 0.3309 0.7365 0.0208 0.099 Uiso 1 1 calc R . .
C21 C 0.6732(4) 0.6748(2) 0.01754(13) 0.0802(6) Uani 1 1 d . . .
H21 H 0.7019 0.6994 -0.0408 0.096 Uiso 1 1 calc R . .
O2 O 0.7472(5) -0.08630(17) 0.42655(19) 0.1654(13) Uani 1 1 d . . .
C22 C 1.1107(4) -0.0865(2) 0.35224(14) 0.0843(6) Uani 1 1 d . . .
H22A H 1.1392 -0.1858 0.3639 0.126 Uiso 1 1 calc R . .
H22B H 1.2282 -0.0550 0.3743 0.126 Uiso 1 1 calc R . .
H22C H 1.1123 -0.0591 0.2917 0.126 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O3 C10 117.38(13) . . ?
C2 C1 C6 111.67(10) . . ?
C2 C1 C5 111.31(10) . . ?
C6 C1 C5 109.22(10) . . ?
O1 C2 C4 119.94(12) . . ?
O1 C2 C1 120.35(12) . . ?
C4 C2 C1 119.61(11) . . ?
C8 C3 C13 118.07(15) . . ?
C8 C3 C5 120.19(12) . . ?
C13 C3 C5 121.74(14) . . ?
C7 C4 C14 118.71(14) . . ?
C7 C4 C2 123.49(12) . . ?
C14 C4 C2 117.80(13) . . ?
O4 C5 C9 106.13(11) . . ?
O4 C5 C3 111.29(11) . . ?
C9 C5 C3 110.75(11) . . ?
O4 C5 C1 110.68(10) . . ?
C9 C5 C1 108.28(11) . . ?
C3 C5 C1 109.61(10) . . ?
C10 C6 C1 114.21(11) . . ?
C10 C6 C11 112.94(12) . . ?
C1 C6 C11 107.70(11) . . ?
C17 C7 C4 120.57(15) . . ?
C19 C8 C3 121.38(15) . . ?
C12 C9 C5 123.37(13) . . ?
O3 C10 C6 108.44(11) . . ?
C12 C11 C6 112.61(12) . . ?
C9 C12 C11 124.44(13) . . ?
C3 C13 C20 120.29(18) . . ?
C16 C14 C4 120.04(17) . . ?
C16 C15 C17 120.05(16) . . ?
C14 C16 C15 120.37(16) . . ?
C15 C17 C7 120.23(18) . . ?
O2 C18 O3 121.75(19) . . ?
O2 C18 C22 125.40(18) . . ?
O3 C18 C22 112.81(16) . . ?
C8 C19 C21 119.96(19) . . ?
C21 C20 C13 120.96(16) . . ?
C20 C21 C19 119.30(18) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C5 1.4291(15) . ?
O3 C18 1.324(2) . ?
O3 C10 1.4410(19) . ?
O1 C2 1.2177(16) . ?
C1 C2 1.5184(17) . ?
C1 C6 1.5404(18) . ?
C1 C5 1.5563(17) . ?
C2 C4 1.4885(19) . ?
C3 C8 1.380(2) . ?
C3 C13 1.382(2) . ?
C3 C5 1.5243(19) . ?
C4 C7 1.385(2) . ?
C4 C14 1.3880(19) . ?
C5 C9 1.5196(18) . ?
C6 C10 1.513(2) . ?
C6 C11 1.531(2) . ?
C7 C17 1.384(2) . ?
C8 C19 1.378(2) . ?
C9 C12 1.311(2) . ?
C11 C12 1.492(2) . ?
C13 C20 1.383(3) . ?
C14 C16 1.388(3) . ?
C15 C16 1.371(3) . ?
C15 C17 1.365(3) . ?
C18 O2 1.178(2) . ?
C18 C22 1.471(3) . ?
C19 C21 1.372(3) . ?
C20 C21 1.366(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26994473
2 PubChem 139190582
