Synthesis of Five-, Six-, and Seven-Membered 1,3- and 1,4-Heterocyclic Compounds via Intramolecular Hydroalkoxylation/Hydrothioalkoxylation of Alkenols/Thioalkenols.
Deka, Manash J.; Indukuri, Kiran; Sultana, Sabera; Borah, Madhurjya; Saikia, Anil K.; The Journal of organic chemistry 80 (2015) 4349–4359; doi:10.1021/acs.joc.5b00049

data_4030958
_publ_section_title
;
 Synthesis of Five-, Six-, and Seven-Membered 1,3- and 1,4-Heterocyclic
 Compounds via Intramolecular Hydroalkoxylation/Hydrothioalkoxylation of
 Alkenols/Thioalkenols.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4349
_journal_page_last               4359
_journal_paper_doi               10.1021/acs.joc.5b00049
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C25 H27 N O3 S'
_chemical_formula_weight         421.54
_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                 91.936(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.2875(3)
_cell_length_b                   10.6142(4)
_cell_length_c                   14.7414(6)
_cell_measurement_temperature    293(2)
_cell_volume                     1139.61(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4159
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.37
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69902
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.13(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3224
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0230P)^2^+0.3228P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0851
_reflns_number_gt                2828
_reflns_number_total             3224
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b00049_si_002.cif
_cod_data_source_block           aks_md_1
_cod_depositor_comments          'Adding full bibliography for 4030958.cif.'
_cod_original_cell_volume        1139.60(8)
_cod_original_sg_symbol_H-M      P21
_cod_database_code               4030958