Synthesis of α-Halo-γ-hydroxyenamides by Titanium Tetrahalide Mediated Addition of Aldehydes or Ketones to Ynamides.
Yabuuchi, Yuto; Kuzuguchi, Takeo; Yoshimura, Tomoyuki; Matsuo, Jun-Ichi; Organic letters 18 (2016) 4951–4953; doi:10.1021/acs.orglett.6b02526

data_1555809
_publ_section_title
;
 Synthesis of \a-Halo-\g-hydroxyenamides by Titanium Tetrahalide Mediated
 Addition of Aldehydes or Ketones to Ynamides.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4951
_journal_page_last               4953
_journal_paper_doi               10.1021/acs.orglett.6b02526
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C23 H22 Cl N O3 S'
_chemical_formula_sum            'C23 H22 Cl N O3 S'
_chemical_formula_weight         427.94
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                95.437(5)
_cell_angle_beta                 101.771(5)
_cell_angle_gamma                115.319(5)
_cell_formula_units_Z            4
_cell_length_a                   12.179(3)
_cell_length_b                   12.639(3)
_cell_length_c                   15.612(3)
_cell_measurement_reflns_used    9040
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.11
_cell_volume                     2081.2(8)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.1'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_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            20232
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        27.450
_diffrn_reflns_theta_max         27.450
_diffrn_reflns_theta_min         3.105
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  0.857
_exptl_absorpt_correction_T_min  0.473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896.00
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_refine_diff_density_max         0.54
_refine_diff_density_min         -0.61
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     469
_refine_ls_number_reflns         9369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1163
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1045P)^2^+0.3792P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1569
_refine_ls_wR_factor_ref         0.2262
_reflns_number_gt                4907
_reflns_number_total             9369
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol6b02526_si_002.cif
_cod_data_source_block           yabuuchi66
_cod_original_cell_volume        2081.3(8)
_cod_database_code               1555809