Palladium-Catalyzed Hydrohalogenation of 1,6-Enynes: Hydrogen Halide Salts and Alkyl Halides as Convenient HX Surrogates.
Petrone, David A.; Franzoni, Ivan; Ye, Juntao; Rodríguez, José F; Poblador-Bahamonde, Amalia I; Lautens, Mark; Journal of the American Chemical Society 139 (2017) 3546–3557; doi:10.1021/jacs.7b00482

data_4125464
_publ_section_title
;
 Palladium-Catalyzed Hydrohalogenation of 1,6-Enynes: Hydrogen Halide
 Salts and Alkyl Halides as Convenient HX Surrogates.
;
_journal_issue                   9
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3546
_journal_page_last               3557
_journal_paper_doi               10.1021/jacs.7b00482
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C17 H22 Br N O2'
_chemical_formula_sum            'C17 H22 Br N O2'
_chemical_formula_weight         352.26
_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_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 95.867(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4581(10)
_cell_length_b                   20.914(3)
_cell_length_c                   12.284(2)
_cell_measurement_reflns_used    8209
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      2.56
_cell_volume                     1650.4(4)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19579
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.625
_diffrn_reflns_theta_min         1.930
_exptl_absorpt_coefficient_mu    2.495
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3824
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0239
_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^)+(0.0212P)^2^+0.7622P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0514
_refine_ls_wR_factor_ref         0.0546
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3196
_reflns_number_total             3824
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b00482_si_003.cif
_cod_data_source_block           d1692
_cod_depositor_comments
'Adding full bibliography for 4125463--4125465.cif.'
_cod_original_cell_volume        1650.5(5)
_cod_database_code               4125464
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.502
_shelx_estimated_absorpt_t_max   0.691
_shelx_res_checksum              52501
_shelx_hkl_checksum              19915