Anti-Markovnikov hydroimination of terminal alkynes in gold-catalyzed pyridine construction from ammonia.
Wang, Liliang; Kong, Lingbing; Li, Yongxin; Ganguly, Rakesh; Kinjo, Rei; Chemical communications (Cambridge, England) 51 (2015) 12419–12422; doi:10.1039/c5cc04091d

data_7117563
_publ_section_title
;
 Anti-Markovnikov hydroimination of terminal alkynes in gold-catalyzed
 pyridine construction from ammonia.
;
_journal_issue                   62
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              12419
_journal_page_last               12422
_journal_paper_doi               10.1039/c5cc04091d
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C43 H57 Au Cl3 N'
_chemical_formula_weight         891.21
_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
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2015-02-26 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.9810(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.7969(9)
_cell_length_b                   9.1006(3)
_cell_length_c                   22.4423(10)
_cell_measurement_reflns_used    8784
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      28.2738
_cell_measurement_theta_min      2.7226
_cell_volume                     4103.2(3)
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_collection       'Bruker Apex2'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_molecular_graphics    'Bruker Apex2'
_computing_publication_material  'Bruker Apex2'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            37965
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    3.810
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_refine_diff_density_max         1.564
_refine_diff_density_min         -1.541
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         10122
_refine_ls_number_restraints     47
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0591P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.1129
_reflns_number_gt                8356
_reflns_number_total             10122
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc04091d2.cif
_cod_data_source_block           I
_cod_database_code               7117563