Palladium(II)-Catalyzed Intramolecular C-H Alkenylation for the Synthesis of Chromanes.
Carral-Menoyo, Asier; Misol, Alexander; Gómez-Redondo, Marcos; Sotomayor, Nuria; Lete, Esther; The Journal of organic chemistry 84 (2019) 2048–2060; doi:10.1021/acs.joc.8b03051

data_4033790
_publ_section_title
;
 Palladium(II)-Catalyzed Intramolecular C-H Alkenylation for the Synthesis
 of Chromanes.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2048
_journal_page_last               2060
_journal_paper_doi               10.1021/acs.joc.8b03051
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C18 H17 F O3'
_chemical_formula_sum            'C18 H17 F O3'
_chemical_formula_weight         300.32
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-09T14:04:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 94.082(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9525(2)
_cell_length_b                   14.6990(8)
_cell_length_c                   24.6043(14)
_cell_measurement_reflns_used    3521
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      74.002
_cell_measurement_theta_min      4.661
_cell_volume                     1425.83(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_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    -35.00  67.00   1.00    1.00    --   41.08 -38.00-150.00  102
  2  \w      5.00  93.00   1.00    1.00    --   41.08-125.00 120.00   88
  3  \w     16.00 107.00   1.00    1.00    --   41.08  38.00  30.00   91
  4  \w     29.00  97.00   1.00    1.00    --   41.08  38.00-180.00   68
  5  \w    -87.00 -42.00   1.00    4.00    --  -83.00 125.00-180.00   45
  6  \w    -89.00 -59.00   1.00    4.00    --  -83.00 -61.00   0.00   30
  7  \w   -147.00-119.00   1.00    4.00    --  -83.00 -61.00   0.00   28
  8  \w     38.00  69.00   1.00    4.00    --  108.36 -30.00-150.00   31
  9  \w     39.00  66.00   1.00    4.00    --  108.36 -45.00  60.00   27
 10  \w     42.00 103.00   1.00    4.00    --  108.36 -94.00  60.00   61
 11  \w    106.00 136.00   1.00    4.00    --  108.36 -61.00 -30.00   30
 12  \w     58.00 135.00   1.00    4.00    --  108.36 -77.00 150.00   77
 13  \w     94.00 132.00   1.00    4.00    --  108.36  30.00 120.00   38
 14  \w     78.00 158.00   1.00    4.00    --  108.36  61.00 -30.00   80
 15  \w    107.00 158.00   1.00    4.00    --  108.36  45.00 -60.00   51
 16  \w     34.00  64.00   1.00    4.00    --  108.36 -30.00 -30.00   30
 17  \w     35.00  63.00   1.00    4.00    --  108.36 -45.00 120.00   28
 18  \w     30.00  69.00   1.00    4.00    --  108.36 -30.00   0.00   39
 19  \w     39.00  66.00   1.00    4.00    --  108.36 -45.00-180.00   27
 20  \w     34.00  61.00   1.00    4.00    --  108.36 -45.00 -30.00   27
 21  \w     35.00 117.00   1.00    4.00    --  108.36-125.00-180.00   82
 22  \w     56.00  83.00   1.00    4.00    --  108.36 -61.00 -30.00   27
 23  \w     37.00 121.00   1.00    4.00    --  108.36-125.00  30.00   84
 24  \w     84.00 142.00   1.00    4.00    --  108.36  45.00-150.00   58
 25  \w     71.00 110.00   1.00    4.00    --  108.36-125.00 -30.00   39
 26  \w    111.00 155.00   1.00    4.00    --  108.36  45.00-120.00   44
 27  \w     48.00  76.00   1.00    4.00    --  108.36 -45.00-120.00   28
;
_diffrn_measurement_device       'four-circle\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0948533
_diffrn_orient_matrix_UB_12      -0.0998614
_diffrn_orient_matrix_UB_13      -0.0127346
_diffrn_orient_matrix_UB_21      -0.0988866
_diffrn_orient_matrix_UB_22      0.0258307
_diffrn_orient_matrix_UB_23      -0.0597004
_diffrn_orient_matrix_UB_31      0.3657768
_diffrn_orient_matrix_UB_32      -0.018879
_diffrn_orient_matrix_UB_33      -0.0146098
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.0978
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10886
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.995
_diffrn_reflns_theta_min         3.505
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.853
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.70922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.639
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.07
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.16
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2649
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.16
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0688
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0622P)^2^+1.7962P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.176
_refine_ls_wR_factor_ref         0.182
_reflns_Friedel_coverage         0
_reflns_number_gt                2207
_reflns_number_total             2649
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03051_si_002.cif
_cod_data_source_block           a20180039_ac941b
_cod_database_code               4033790