Palladium-Catalyzed Aerobic Oxidative Coupling of <i>ortho</i>-(Alkynyl)styrenes with Allylic Alcohols via 6-<i>endo-dig</i> Cyclization: Regioselective Construction of Polysubstituted Naphthalenes.
Ramesh, Perla; Satyanarayana, Gedu; The Journal of organic chemistry 84 (2019) 12856–12870; doi:10.1021/acs.joc.9b01240

data_4034081
_publ_section_title
;
 Palladium-Catalyzed Aerobic Oxidative Coupling of
 <i>ortho</i>-(Alkynyl)styrenes with Allylic Alcohols via
 6-<i>endo-dig</i> Cyclization: Regioselective Construction of
 Polysubstituted Naphthalenes.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12856
_journal_page_last               12870
_journal_paper_doi               10.1021/acs.joc.9b01240
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C33 H28 O3'
_chemical_formula_sum            'C33 H28 O3'
_chemical_formula_weight         472.59
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-06-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.8742(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.19794(19)
_cell_length_b                   17.6415(3)
_cell_length_c                   14.5974(3)
_cell_measurement_reflns_used    3616
_cell_measurement_temperature    293
_cell_measurement_theta_max      69.8020
_cell_measurement_theta_min      4.0110
_cell_volume                     2538.18(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9805
_diffrn_measured_fraction_theta_max 0.9805
_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     11.00  64.00   1.00    1.00    --    0.00  57.00  90.00   53
  2  \w    -20.00   7.00   1.00    1.00    --    0.00  57.00  90.00   27
  3  \w     13.00  40.00   1.00    1.00    --    0.00  38.00-120.00   27
  4  \w     -9.00  62.00   1.00    1.51    --   54.00 -57.00-180.00   71
  5  \w     40.00  96.00   1.00    1.51    --   54.00  57.00 150.00   56
  6  \w     47.00  91.00   1.00    1.51    --   54.00-125.00   0.00   44
  7  \w      0.00  81.00   1.00    1.51    --   54.00 -38.00   0.00   81
  8  \w     57.00 106.00   1.00    1.51    --   54.00  57.00   0.00   49
  9  \w     58.00 100.00   1.00    1.51    --  108.00 178.00   0.00   42
 10  \w    132.00 170.00   1.00    1.51    --  108.00  77.00 -30.00   38
 11  \w     37.00  81.00   1.00    1.51    --  108.00 -77.00-120.00   44
 12  \w     37.00 108.00   1.00    1.51    --  108.00-111.00 -30.00   71
 13  \w     38.00 132.00   1.00    1.51    --  108.00 -38.00 -30.00   94
 14  \w     75.00 100.00   1.00    1.51    --  108.00  25.00 150.00   25
 15  \w    142.00 178.00   1.00    1.51    --  108.00  25.00 150.00   36
 16  \w     98.00 135.00   1.00    1.51    --  108.00 -77.00-120.00   37
 17  \w     38.00 109.00   1.00    1.51    --  108.00-111.00-150.00   71
 18  \w    115.00 167.00   1.00    1.51    --  108.00  63.00 -60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0710187000
_diffrn_orient_matrix_UB_12      -0.0218602000
_diffrn_orient_matrix_UB_13      -0.1030106000
_diffrn_orient_matrix_UB_21      -0.0281784000
_diffrn_orient_matrix_UB_22      0.0843405000
_diffrn_orient_matrix_UB_23      -0.0248329000
_diffrn_orient_matrix_UB_31      0.1363159000
_diffrn_orient_matrix_UB_32      0.0059278000
_diffrn_orient_matrix_UB_33      -0.0265602000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9569
_diffrn_reflns_theta_full        69.9863
_diffrn_reflns_theta_max         69.99
_diffrn_reflns_theta_min         4.01
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2366
_exptl_crystal_description       block
_exptl_crystal_F_000             1003.0469
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.1667
_refine_diff_density_min         -0.2343
_refine_diff_density_rms         0.0538
_refine_ls_d_res_high            0.8205
_refine_ls_d_res_low             11.0182
_refine_ls_goodness_of_fit_ref   1.0894
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    50
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0894
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0620P)^2^+0.1150P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1310
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -12
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              -8
_reflns_number_gt                3544
_reflns_number_total             4725
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo9b01240_si_002.cif
_cod_data_source_block           exp_8735
_cod_original_cell_volume        2538.17(8)
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               4034081
_chemical_oxdiff_formula         'C33 H28 O3'
_reflns_odcompleteness_completeness 100.00
_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 Secondary CH2 refined with riding coordinates:
 C23(H23a,H23b), C24(H24a,H24b)
2.b Aromatic/amide H refined with riding coordinates:
 C28(H28), C27(H27), C31(H31), C3(H3), C15(H15), C14(H14), C13(H13), C12(H12),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C6(H6), C7(H7), C8(H8),
 C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C32(H32a,H32b,H32c), C33(H33a,H33b,H33c)
;
_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 1.322
_oxdiff_exptl_absorpt_empirical_full_min 0.802