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_7117558
_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            'C21 H14 Br F2 N'
_chemical_formula_weight         398.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2015-02-26 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 119.1045(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1103(4)
_cell_length_b                   19.8612(7)
_cell_length_c                   8.6893(3)
_cell_measurement_reflns_used    3705
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      26.4533
_cell_measurement_theta_min      2.3352
_cell_volume                     1675.31(11)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11979
_diffrn_reflns_theta_full        31.02
_diffrn_reflns_theta_max         31.02
_diffrn_reflns_theta_min         2.68
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.477
_exptl_absorpt_correction_T_max  0.64
_exptl_absorpt_correction_T_min  0.53
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.336
_refine_ls_abs_structure_details
;
Flack x determined using 1446 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4527
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0329
_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^)+(0.0315P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0635
_refine_ls_wR_factor_ref         0.0666
_reflns_number_gt                3928
_reflns_number_total             4527
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc04091d2.cif
_cod_data_source_block           I
_cod_original_cell_volume        1675.31(10)
_cod_database_code               7117558
_shelx_res_checksum              18694
_shelx_hkl_checksum              47302