Cyclic Ether Synthesis via Palladium-Catalyzed Directed Dehydrogenative Annulation at Unactivated Terminal Positions.
Thompson, Samuel J.; Thach, Danny Q.; Dong, Guangbin; Journal of the American Chemical Society 137 (2015) 11586–11589; doi:10.1021/jacs.5b07384

data_4129505
_publ_section_title
;
 Cyclic Ether Synthesis via Palladium-Catalyzed Directed Dehydrogenative
 Annulation at Unactivated Terminal Positions.
;
_journal_issue                   36
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11586
_journal_page_last               11589
_journal_paper_doi               10.1021/jacs.5b07384
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C19 H29 N O4'
_chemical_formula_sum            'C19 H29 N O4'
_chemical_formula_weight         335.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
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_atom_sites_solution_hydrogens   mixed
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_cell_angle_beta                 90.690(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9305(4)
_cell_length_b                   20.1095(13)
_cell_length_c                   15.573(2)
_cell_measurement_reflns_used    1903
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.8
_cell_measurement_theta_min      3.57
_cell_volume                     1857.1(3)
_computing_cell_refinement
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_data_collection
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_data_reduction
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'Shelxl-2013, Sheldrick, G. M.'
_computing_structure_solution
;

SUPERFLIP.  Palatinus, L. and Chapuis, G., J. Appl. Cryst. 40, 786-790.
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'Agilent SuperNova with AtlasS2 CCD'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0996
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5806
_diffrn_reflns_point_group_measured_fraction_full 0.831
_diffrn_reflns_point_group_measured_fraction_max 0.781
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.452
_diffrn_reflns_theta_min         2.838
_diffrn_source                   'sealed microfocus tube'
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Empirical correction (ABSPACK) includes:
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.286
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         5806
_refine_ls_number_restraints     295
_refine_ls_restrained_S_all      1.267
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.1017
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1200P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2649
_refine_ls_wR_factor_ref         0.2814
_reflns_Friedel_coverage         0.605
_reflns_Friedel_fraction_full    0.667
_reflns_Friedel_fraction_max     0.607
_reflns_number_gt                4891
_reflns_number_total             5806
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b07384_si_002.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4129505
_shelx_estimated_absorpt_t_min   0.804
_shelx_estimated_absorpt_t_max   0.980
_shelxl_version_number           2013-4
_shelx_res_checksum              62145
_shelx_hkl_checksum              83945