Iron(II) Halide Promoted Cyclization of Cyclic 2-Enynamides: Stereoselective Synthesis of Halogenated Bicyclic γ-Lactams.
Yeh, Ming-Chang P; Shiue, Yuan-Shin; Lin, Hsin-Hui; Yu, Tzu-Yu; Hu, Ting-Chia; Hong, Jia-Jyun; Organic letters 18 (2016) 2407–2410; doi:10.1021/acs.orglett.6b00916

data_1543814
_publ_section_title
;
 Iron(II) Halide Promoted Cyclization of Cyclic 2-Enynamides:
 Stereoselective Synthesis of Halogenated Bicyclic \g-Lactams.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2407
_journal_page_last               2410
_journal_paper_doi               10.1021/acs.orglett.6b00916
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C23 H26 Cl N O3 S'
_chemical_formula_sum            'C23 H26 Cl N O3 S'
_chemical_formula_weight         431.96
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.328(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.1254(7)
_cell_length_b                   14.0815(11)
_cell_length_c                   10.0099(8)
_cell_measurement_reflns_used    5174
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.06
_cell_measurement_theta_min      2.61
_cell_volume                     1073.98(15)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_sigmaI/netI    0.0836
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6534
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_T_max  0.9764
_exptl_absorpt_correction_T_min  0.8088
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.74
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.368
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.21(17)
_refine_ls_extinction_coef       0.018(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3316
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0908
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1221P)^2^+3.9536P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2392
_refine_ls_wR_factor_ref         0.2433
_reflns_number_gt                3102
_reflns_number_total             3316
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00916_si_006.cif
_cod_data_source_block           a17460
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1543814