Palladium(II)-Catalyzed Directed anti-Hydrochlorination of Unactivated Alkynes with HCl.
Derosa, Joseph; Cantu, Annabelle L.; Boulous, Mark N.; O'Duill, Miriam L; Turnbull, Joshua L.; Liu, Zhen; De La Torre, Daizy M.; Engle, Keary M.; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b00892

data_4126307
_publ_section_title
;
 Palladium(II)-Catalyzed Directed anti-Hydrochlorination of Unactivated
 Alkynes with HCl.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b00892
_journal_year                    2017
_chemical_formula_moiety         'C15 H13 Cl N2 O'
_chemical_formula_sum            'C15 H13 Cl N2 O'
_chemical_formula_weight         272.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.998(7)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   13.195(4)
_cell_length_b                   28.087(7)
_cell_length_c                   10.834(3)
_cell_measurement_reflns_used    2700
_cell_measurement_temperature    100
_cell_measurement_theta_max      23.56
_cell_measurement_theta_min      2.39
_cell_volume                     3985.3(19)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            25934
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.375
_diffrn_reflns_theta_min         1.716
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_max  0.2602
_exptl_absorpt_correction_T_min  0.2142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0542 before and 0.0485 after correction.
The Ratio of minimum to maximum transmission is 0.8232.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       plate
_exptl_crystal_F_000             1704
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     514
_refine_ls_number_reflns         8145
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0356P)^2^+0.9781P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1092
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5346
_reflns_number_total             8145
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b00892_si_002.cif
_cod_data_source_block           engle17_a
_cod_original_cell_volume        3985.3(18)
_cod_database_code               4126307
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.928
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7A(H7AA,H7AB), C7B(H7BA,H7BB), C7C(H7CA,H7CB)
2.b Aromatic/amide H refined with riding coordinates:
 N2C(H2C), N2B(H2B), N2A(H2A), C9B(H9B), C4C(H4C), C11B(H11B), C3A(H3A),
 C4B(H4B), C3B(H3B), C9C(H9C), C2A(H2AA), C11C(H11C), C1C(H1C), C4A(H4A),
 C3C(H3C), C9A(H9A), C2B(H2BA), C15B(H15B), C15C(H15C), C14C(H14C), C2C(H2CA),
 C12B(H12B), C1A(H1A), C1B(H1B), C13C(H13C), C12C(H12C), C13B(H13B), C15A(H15A),
  C14B(H14B), C11A(H11A), C14A(H14A), C12A(H12A), C13A(H13A)
;
_shelx_res_checksum              17149
_shelx_hkl_checksum              81664
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'