Terminal Alkyne-Assisted One-Pot Synthesis of Arylamidines: Carbon Source of the Amidine Group from Oxime Chlorides.
Yi, Fengping; Sun, Qihui; Sun, Jing; Fu, Chao; Yi, Weiyin; The Journal of organic chemistry 84 (2019) 6780–6787; doi:10.1021/acs.joc.9b00538

data_4034629
_publ_section_title
;
 Terminal Alkyne-Assisted One-Pot Synthesis of Arylamidines: Carbon Source
 of the Amidine Group from Oxime Chlorides.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6780
_journal_page_last               6787
_journal_paper_doi               10.1021/acs.joc.9b00538
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C14 H14 N2 O2 S'
_chemical_formula_sum            'C14 H14 N2 O2 S'
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_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
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_cell_length_c                   16.9333(6)
_cell_measurement_reflns_used    7973
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.57
_cell_measurement_theta_min      4.12
_cell_volume                     1305.15(8)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11819
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.638
_diffrn_reflns_theta_max         66.638
_diffrn_reflns_theta_min         4.124
_exptl_absorpt_coefficient_mu    2.204
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.7528
_exptl_transmission_factor_min   0.5139
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0314
_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^)+(0.0431P)^2^+0.6129P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0843
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2139
_reflns_number_total             2302
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00538_si_002.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4034629
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.667
_shelx_estimated_absorpt_t_max   0.667
_shelx_res_checksum              99053
_shelx_hkl_checksum              79554