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_1543817
_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         'C21 H22 Br N O3 S'
_chemical_formula_sum            'C21 H22 Br N O3 S'
_chemical_formula_weight         448.37
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.544(2)
_cell_length_b                   6.9600(5)
_cell_length_c                   24.234(2)
_cell_measurement_reflns_used    7926
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.69
_cell_measurement_theta_min      2.42
_cell_volume                     3971.1(6)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0578
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            25133
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    2.197
_exptl_absorpt_correction_T_max  0.4970
_exptl_absorpt_correction_T_min  0.2932
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.74
_exptl_crystal_size_mid          0.63
_exptl_crystal_size_min          0.37
_refine_diff_density_max         1.038
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.408(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         6695
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0715P)^2^+8.4022P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1334
_reflns_number_gt                5245
_reflns_number_total             6695
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00916_si_003.cif
_cod_data_source_block           a17250
_cod_original_cell_volume        3971.2(6)
_cod_database_code               1543817