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_4032988
_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         'C22 H24 F N O3 S'
_chemical_formula_sum            'C22 H24 F N O3 S'
_chemical_formula_weight         401.48
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_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            4
_cell_length_a                   11.726(6)
_cell_length_b                   25.881(12)
_cell_length_c                   6.436(3)
_cell_measurement_reflns_used    1683
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.22
_cell_measurement_theta_min      2.92
_cell_volume                     1953.2(16)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0560
_diffrn_reflns_av_sigmaI/netI    0.0671
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9508
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.9980
_exptl_absorpt_correction_T_min  0.8671
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.74
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.14(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.873
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2853
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.873
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0895P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1282
_reflns_number_gt                2198
_reflns_number_total             2853
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02158_si_002.cif
_cod_data_source_block           17765_3j_CCDC_1491126
_cod_depositor_comments
'Adding full bibliography for 4032987--4032992.cif.'
_cod_original_cell_volume        1953.2(17)
_cod_database_code               4032988