Palladium Catalyzed Regioselective Elimination-Hydrocarbonylation of Propargylic Alcohols
Yuan, Yuan; Jia, Minqiang; Zhang, Wanli; Ma, Shengming; Chemical Communications  (2019) –; doi:10.1039/C9CC03262B

data_7123635
_publ_section_title
;
 Palladium Catalyzed Regioselective Elimination-Hydrocarbonylation of
 Propargylic Alcohols
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC03262B
_journal_year                    2019
_chemical_formula_moiety         'C15 H18 O2'
_chemical_formula_sum            'C15 H18 O2'
_chemical_formula_weight         230.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-10-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-10-26 deposited with the CCDC.    2019-06-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 89.897(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.7690(2)
_cell_length_b                   17.0752(4)
_cell_length_c                   18.1342(3)
_cell_measurement_reflns_used    12959
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.5750
_cell_measurement_theta_min      4.8550
_cell_volume                     2715.27(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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    -88.00 -62.00   1.00    1.00    --    0.00 -77.00 -89.00   26
  2  \w    -44.00 -17.00   1.00    1.00    --    0.00 -77.00 -89.00   27
  3  \w     33.00  79.00   1.00    2.00    --   95.80 -77.00 -89.00   46
  4  \w     65.00  98.00   1.00    2.00    --   95.80  77.00  36.00   33
  5  \w    -19.00  26.00   1.00    1.00    --    0.00  38.00-120.00   45
  6  \w     58.00  84.00   1.00    1.00    --    0.00  38.00-150.00   26
  7  \w    -23.00  32.00   1.00    1.00    --    0.00  57.00 120.00   55
  8  \w     52.00  81.00   1.00    1.00    --    0.00  38.00-120.00   29
  9  \w     36.00  89.00   1.00    1.00    --    0.00  57.00 120.00   53
 10  \w    -11.00  26.00   1.00    1.00    --    0.00  77.00  36.00   37
 11  \w     44.00  85.00   1.00    1.00    --    0.00  57.00   0.00   41
 12  \w     52.00  88.00   1.00    1.00    --    0.00  38.00 -90.00   36
 13  \w    -20.00  41.00   1.00    1.00    --    0.00  57.00   0.00   61
 14  \w    -17.00  16.00   1.00    1.00    --    0.00  38.00-150.00   33
 15  \w    -23.00   9.00   1.00    1.00    --    0.00  19.00 120.00   32
 16  \w     56.00  89.00   1.00    1.00    --    0.00  57.00-180.00   33
 17  \w    -10.00  36.00   1.00    1.00    --    0.00  38.00 -90.00   46
 18  \w    -18.00  33.00   1.00    1.00    --    0.00  57.00-180.00   51
 19  \w     63.00  88.00   1.00    2.00    --   95.80  82.00 120.00   25
 20  \w     65.00  91.00   1.00    2.00    --   95.80  77.00-180.00   26
 21  \w      7.00  34.00   1.00    2.00    --   95.80 -82.00  60.00   27
 22  \w     75.00 123.00   1.00    2.00    --   95.80  45.00 -90.00   48
 23  \w     63.00  92.00   1.00    2.00    --   95.80  82.00  90.00   29
 24  \w    144.00 170.00   1.00    2.00    --   95.80  77.00-150.00   26
 25  \w     66.00  92.00   1.00    2.00    --   95.80  82.00 -30.00   26
 26  \w     61.00 128.00   1.00    2.00    --   95.80 -82.00   0.00   67
 27  \w     64.00  99.00   1.00    2.00    --   95.80  82.00-150.00   35
 28  \w     80.00 184.00   1.00    2.00    --   95.80  45.00-180.00  104
 29  \w      6.00 128.00   1.00    2.00    --   95.80 -82.00 -90.00  122
 30  \w     65.00  92.00   1.00    2.00    --   95.80  77.00   0.00   27
 31  \w    102.00 128.00   1.00    2.00    --   95.80  77.00   0.00   26
 32  \w     75.00 170.00   1.00    2.00    --   95.80  45.00  60.00   95
 33  \w     74.00 104.00   1.00    2.00    --   95.80  50.00 153.25   30
 34  \w    118.00 144.00   1.00    2.00    --   95.80  50.00 153.25   26
 35  \w     11.00  46.00   1.00    2.00    --   95.80 -82.00   0.00   35
 36  \w     65.00  90.00   1.00    2.00    --   95.80  77.00 -60.00   25
 37  \w     71.00  98.00   1.00    2.00    --   95.80  61.00-150.00   27
 38  \w    155.00 181.00   1.00    2.00    --   95.80  82.00   0.00   26
 39  \w     65.00  91.00   1.00    2.00    --   95.80  77.00-150.00   26
 40  \w     66.00 102.00   1.00    2.00    --   95.80  77.00 -30.00   36
 41  \w     75.00 142.00   1.00    2.00    --   95.80  45.00  90.00   67
 42  \w     76.00 124.00   1.00    2.00    --   95.80  45.00  30.00   48
 43  \w     17.00 128.00   1.00    2.00    --   95.80 -82.00-150.00  111
 44  \w    150.00 176.00   1.00    2.00    --   95.80  82.00-120.00   26
 45  \w     76.00 112.00   1.00    2.00    --   95.80  45.00-120.00   36
 46  \w    121.00 175.00   1.00    2.00    --   95.80  45.00-120.00   54
 47  \w     75.00 110.00   1.00    2.00    --   95.80  45.00 -30.00   35
 48  \w    133.00 177.00   1.00    2.00    --   95.80  45.00 -30.00   44
 49  \w     75.00 103.00   1.00    2.00    --   95.80  45.00 150.00   28
 50  \w     63.00  89.00   1.00    2.00    --   95.80  82.00  30.00   26
 51  \w     75.00 108.00   1.00    2.00    --   95.80  45.00 -60.00   33
 52  \w    138.00 184.00   1.00    2.00    --   95.80  45.00 -60.00   46
 53  \w     63.00  89.00   1.00    2.00    --   95.80  82.00   0.00   26
 54  \w    117.00 182.00   1.00    2.00    --   95.80  79.00-105.61   65
 55  \w     71.00  97.00   1.00    2.00    --   95.80  61.00 -60.00   26
 56  \w    160.00 185.00   1.00    2.00    --   95.80  61.00 -60.00   25
 57  \w     72.00  98.00   1.00    2.00    --   95.80  61.00  30.00   26
 58  \w     71.00  97.00   1.00    2.00    --   95.80  61.00  90.00   26
 59  \w    130.00 185.00   1.00    2.00    --   95.80  61.00  90.00   55
 60  \w     63.00  89.00   1.00    2.00    --   95.80  82.00 -60.00   26
 61  \w     63.00  88.00   1.00    2.00    --   95.80  82.00  60.00   25
 62  \w     63.00  89.00   1.00    2.00    --   95.80  82.00 150.00   26
 63  \w    124.00 182.00   1.00    2.00    --   95.80  82.00 150.00   58
 64  \w     78.00 150.00   1.00    2.00    --   95.80  45.00 120.00   72
 65  \w     64.00  90.00   1.00    2.00    --   95.80  79.00-105.61   26
 66  \w     63.00  88.00   1.00    2.00    --   95.80  82.00-120.00   25
 67  \w     63.00  89.00   1.00    2.00    --   95.80  82.00 -90.00   26
 68  \w     68.00  93.00   1.00    2.00    --   95.80  69.00 145.67   25
 69  \w    160.00 185.00   1.00    2.00    --   95.80  61.00-180.00   25
 70  \w    142.00 184.00   1.00    2.00    --   95.80  57.00 -17.00   42
 71  \w    125.00 183.00   1.00    2.00    --   95.80  82.00 -90.00   58
 72  \w     72.00 106.00   1.00    2.00    --   95.80  57.00 -17.00   34
 73  \w     73.00  99.00   1.00    2.00    --   95.80  61.00-180.00   26
 74  \w    124.00 149.00   1.00    2.00    --   95.80  82.00 120.00   25
 75  \w     57.00 123.00   1.00    2.00    --   95.80 -82.00  60.00   66
 76  \w    145.00 170.00   1.00    2.00    --   95.80  82.00 -30.00   25
 77  \w     86.00 128.00   1.00    2.00    --   95.80 -82.00 120.00   42
 78  \w     66.00  92.00   1.00    2.00    --   95.80  77.00 -90.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0372172000
_diffrn_orient_matrix_UB_12      0.0563974000
_diffrn_orient_matrix_UB_13      0.0638437000
_diffrn_orient_matrix_UB_21      0.1134863000
_diffrn_orient_matrix_UB_22      0.0601846000
_diffrn_orient_matrix_UB_23      -0.0317327000
_diffrn_orient_matrix_UB_31      -0.1287381000
_diffrn_orient_matrix_UB_32      0.0366746000
_diffrn_orient_matrix_UB_33      -0.0461889000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29293
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.051
_diffrn_reflns_theta_max         67.051
_diffrn_reflns_theta_min         4.877
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0036(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0719
_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^)+(0.1380P)^2^+1.1060P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2203
_refine_ls_wR_factor_ref         0.2259
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2120
_reflns_number_total             2375
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc03262b2.cif
_cod_data_source_block           exp_50
_cod_database_code               7123635
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.836
_shelx_estimated_absorpt_t_min   0.793
_reflns_odcompleteness_completeness 99.96
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C12(H12A,H12B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C5(H5), C11(H11), C2(H2), C4(H4), C3(H3)
2.c Tetrahedral OH refined with riding coordinates:
 O1(H1)
2.d X=CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              84011
_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 2.461
_oxdiff_exptl_absorpt_empirical_full_min 0.372