Synthesis of Spirolactams and Fused Bicyclic Lactams via Acid-Promoted Cyclolactamization of (Ethynyl(tosyl)amino)methyl-Tethered Cyclohex-2-enols.
Tung, Po-Ting; Zhong, Chang-Zhi; Chien, Tzu-Chiang; Yeh, Ming-Chang P; The Journal of organic chemistry 82 (2017) 11543–11557; doi:10.1021/acs.joc.7b02158

data_4032990
_publ_section_title
;
 Synthesis of Spirolactams and Fused Bicyclic Lactams via Acid-Promoted
 Cyclolactamization of (Ethynyl(tosyl)amino)methyl-Tethered
 Cyclohex-2-enols.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11543
_journal_page_last               11557
_journal_paper_doi               10.1021/acs.joc.7b02158
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C23 H25 N O4 S'
_chemical_formula_sum            'C23 H25 N O4 S'
_chemical_formula_weight         411.50
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 104.036(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1794(7)
_cell_length_b                   33.379(3)
_cell_length_c                   7.7820(7)
_cell_measurement_reflns_used    3688
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.85
_cell_measurement_theta_min      2.44
_cell_volume                     2061.2(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0514
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14351
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.57
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_correction_T_min  0.8883
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0481
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0709P)^2^+0.7927P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1325
_reflns_number_gt                2841
_reflns_number_total             3644
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02158_si_002.cif
_cod_data_source_block           a17752_4_CCDC_1491137
_cod_depositor_comments
'Adding full bibliography for 4032987--4032992.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4032990