Direct Transformation of Terminal Alkynes into Amidines by a Silver-Catalyzed Four-Component Reaction.
Liu, Binbin; Ning, Yongquan; Virelli, Matteo; Zanoni, Giuseppe; Anderson, Edward A.; Bi, Xihe; Journal of the American Chemical Society 141 (2019) 1593–1598; doi:10.1021/jacs.8b11039

data_4128090
_publ_section_title
;
 Direct Transformation of Terminal Alkynes into Amidines by a
 Silver-Catalyzed Four-Component Reaction.
;
_journal_issue                   4
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1593
_journal_page_last               1598
_journal_paper_doi               10.1021/jacs.8b11039
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C14 H13 Br N2 O2 S'
_chemical_formula_sum            'C14 H13 Br N2 O2 S'
_chemical_formula_weight         353.23
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-09-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 117.046(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1833(11)
_cell_length_b                   12.8900(9)
_cell_length_c                   10.9328(13)
_cell_measurement_reflns_used    1501
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.5070
_cell_measurement_theta_min      3.8210
_cell_volume                     1403.6(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measurement_device_type  'multiwire proportional'
_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  0.0332
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6159
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.271
_diffrn_reflns_theta_min         3.730
_exptl_absorpt_coefficient_mu    3.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.730
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0555
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.7643P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1351
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2106
_reflns_number_total             3238
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b11039_si_002.cif
_cod_data_source_block           1
_cod_database_code               4128090
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.748
_shelx_estimated_absorpt_t_min   0.709
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C14(H14), C6(H6), C11(H11), C3(H3), C10(H10), C13(H13), C7(H7)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'