Palladium mediated one-pot synthesis of 3-aryl-cyclohexenones and 1,5-diketones from allyl alcohols and aryl ketones.
Samser, Shaikh; Biswal, Priyabrata; Meher, Sushanta Kumar; Venkatasubbaiah, Krishnan; Organic & biomolecular chemistry 19 (2021) 1386–1394; doi:10.1039/d0ob02515a

data_7157843
_publ_section_title
;
 Palladium mediated one-pot synthesis of 3-aryl-cyclohexenones and
 1,5-diketones from allyl alcohols and aryl ketones.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1386
_journal_page_last               1394
_journal_paper_doi               10.1039/d0ob02515a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C15 H16 O'
_chemical_formula_sum            'C15 H16 O'
_chemical_formula_weight         212.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-30
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2020-08-13 deposited with the CCDC.	2021-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.551(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9714(15)
_cell_length_b                   6.6608(7)
_cell_length_c                   19.405(3)
_cell_measurement_reflns_used    2981
_cell_measurement_temperature    114(1)
_cell_measurement_theta_max      72.5770
_cell_measurement_theta_min      4.5500
_cell_volume                     1146.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      114(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -98.00 -10.00   0.50    4.50    --  -38.50 139.00   5.00  176
  2  \w    -93.00  -6.00   0.50    4.50    --  -38.50 130.00-168.00  174
  3  \w     28.00 102.00   0.50    4.50    --   47.81-130.00 118.00  148
  4  \w     32.00 107.00   0.50    4.50    --   47.81-139.00 -55.00  150
  5  \w     40.00 128.00   0.50   18.00    --  102.63-139.00 -55.00  176
  6  \w     39.00 121.00   0.50   18.00    --  102.63-130.00 118.00  164
  7  \w     86.00 166.00   0.50   18.00    --  102.63 139.00   5.00  160
  8  \w     92.00 167.00   0.50   18.00    --  102.63 130.00-168.00  150
  9  \w   -103.00 -15.00   0.50    4.50    --  -38.50 -77.00  30.00  176
 10  \w    -44.00  31.00   0.50    4.50    --  -38.50  19.00 -60.00  150
 11  \w   -101.00 -27.00   0.50    4.50    --  -38.50 -57.00 120.00  148
 12  \w     25.00 112.00   0.50    4.50    --   47.81  77.00-120.00  174
 13  \w     45.00 114.00   0.50    4.50    --   47.81  37.00   0.00  138
 14  \w     38.00 107.00   0.50   18.00    --  102.63 -45.00 -90.00  138
 15  \w     35.00 106.00   0.50   18.00    --  102.63 -30.00 120.00  142
 16  \w     34.00 111.00   0.50   18.00    --  102.63 -15.00 -60.00  154
 17  \w     94.00 168.00   0.50   18.00    --  102.63 125.00 150.00  148
 18  \w     38.00 107.00   0.50   18.00    --  102.63 -45.00  90.00  138
 19  \w     33.00 171.00   0.50   18.00    --  102.63   0.00-120.00  276
 20  \w     38.00 107.00   0.50   18.00    --  102.63 -45.00-180.00  138
 21  \w     98.00 167.00   0.50   18.00    --  102.63  45.00-120.00  138
 22  \w     38.00 118.00   0.50   18.00    --  102.63-125.00 150.00  160
 23  \w     40.00 116.00   0.50   18.00    --  102.63 -61.00  90.00  152
 24  \w     38.00 126.00   0.50   18.00    --  102.63 -77.00   0.00  176
 25  \w     38.00 118.00   0.50   18.00    --  102.63-125.00 -60.00  160
 26  \w     40.00 116.00   0.50   18.00    --  102.63 -61.00 120.00  152
 27  \w     38.00 126.00   0.50   18.00    --  102.63 -77.00 -90.00  176
 28  \w     94.00 168.00   0.50   18.00    --  102.63 125.00-120.00  148
 29  \w     90.00 165.00   0.50   18.00    --  102.63  61.00 -60.00  150
 30  \w     98.00 167.00   0.50   18.00    --  102.63  45.00 -90.00  138
 31  \w     40.00 116.00   0.50   18.00    --  102.63 -61.00-120.00  152
 32  \w     39.00 125.00   0.50   18.00    --  102.63-134.00-178.03  172
 33  \w     95.00 171.00   0.50   18.00    --  102.63  15.00 -30.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0315758000
_diffrn_orient_matrix_UB_12      -0.0611763000
_diffrn_orient_matrix_UB_13      0.0729333000
_diffrn_orient_matrix_UB_21      -0.1229495000
_diffrn_orient_matrix_UB_22      -0.1470782000
_diffrn_orient_matrix_UB_23      -0.0333279000
_diffrn_orient_matrix_UB_31      0.1188538000
_diffrn_orient_matrix_UB_32      -0.1675917000
_diffrn_orient_matrix_UB_33      0.0027112000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1362
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13865
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        66.592
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         4.609
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.280
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.280
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.1022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2919
_refine_ls_wR_factor_ref         0.3190
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1406
_reflns_number_total             1899
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02515a2.cif
_cod_data_source_block           sam-1-tet-3p2
_cod_depositor_comments          'Adding full bibliography for 7157843.cif.'
_cod_database_code               7157843
_chemical_oxdiff_formula         'C60 H56 O4 '
_diffrn_oxdiff_ac3_digest_frames
;
01f2f0683f30fc2f87081b32fbe5d614440002693bf
;
_diffrn_oxdiff_ac3_digest_hkl
;
015369af02c5ba0c7b6f240e510ebb328542de
;
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C14(H14A,H14B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C8(H8), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              22703
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.353
_oxdiff_exptl_absorpt_empirical_full_min 0.219