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_4032987
_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 H27 N O3 S'
_chemical_formula_sum            'C23 H27 N O3 S'
_chemical_formula_weight         397.52
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                71.774(3)
_cell_angle_beta                 71.026(3)
_cell_angle_gamma                61.633(3)
_cell_formula_units_Z            2
_cell_length_a                   9.3182(4)
_cell_length_b                   9.6671(5)
_cell_length_c                   13.9480(7)
_cell_measurement_reflns_used    6252
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.44
_cell_volume                     1026.41(9)
_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 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8922
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.9376
_exptl_absorpt_correction_T_min  0.9164
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.887
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.887
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0633P)^2^+0.7711P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1105
_reflns_number_gt                3201
_reflns_number_total             3582
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02158_si_002.cif
_cod_data_source_block           ch17957_3c_CCDC1491138
_cod_depositor_comments
'Adding full bibliography for 4032987--4032992.cif.'
_cod_database_code               4032987