Triphenylphosphine promoted regio and stereoselective α-halogenation of ynamides
Prabagar, B.; Nayak, Sanatan; Mallick, Rajendra K.; Prasad, Rangu; Sahoo, Akhila K.; Organic Chemistry Frontiers 3 (2016) 110–; doi:10.1039/C5QO00345H

data_1553205
_publ_section_title
;
 Triphenylphosphine promoted regio and stereoselective \a-halogenation of
 ynamides
;
_journal_issue                   1
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              110
_journal_paper_doi               10.1039/C5QO00345H
_journal_volume                  3
_journal_year                    2016
_chemical_formula_sum            'C22 H20 Cl N O2 S'
_chemical_formula_weight         397.90
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'I -2ya'
_symmetry_space_group_name_H-M   'I 1 a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-11-02 deposited with the CCDC.
2015-11-30 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 111.393(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4861(4)
_cell_length_b                   14.0594(4)
_cell_length_c                   13.4860(4)
_cell_measurement_temperature    293(2)
_cell_volume                     2027.77(12)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics    'Mercury v. 1.3 (CCDC)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3532
_diffrn_reflns_theta_full        71.77
_diffrn_reflns_theta_max         71.77
_diffrn_reflns_theta_min         4.72
_exptl_absorpt_coefficient_mu    2.758
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(REQAB; Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       round
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.59(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2273
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1169P)^2^+0.6849P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1455
_reflns_number_gt                2237
_reflns_number_total             2273
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00345h3.cif
_cod_data_source_block           pbr
_cod_original_cell_volume        2027.76(11)
_cod_original_sg_symbol_H-M      'I a'
_cod_database_code               1553205