Synthesis of polysubstituted 3,4-dihydro-2H-thiopyrans by regioselective annulation of 3,3-disubstituted allylic alcohols with a β-oxodithioester
Kurva, Srinivas; Sriramoju, Vinodkumar; Madabhushi, Sridhar; Nanubolu, Jagadeesh Babu; New J. Chem. 41 (2017) 13219–13221; doi:10.1039/C7NJ03025H

data_7056674
_publ_section_title
;
 Synthesis of polysubstituted 3,4-dihydro-2H-thiopyrans by regioselective
 annulation of 3,3-disubstituted allylic alcohols with a \b-oxodithioester
;
_journal_issue                   22
_journal_name_full               'New J. Chem.'
_journal_page_first              13219
_journal_page_last               13221
_journal_paper_doi               10.1039/C7NJ03025H
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C15 H17 Cl O S2'
_chemical_formula_sum            'C15 H17 Cl O S2'
_chemical_formula_weight         312.86
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-07-10 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                85.6620(10)
_cell_angle_beta                 83.5850(10)
_cell_angle_gamma                86.6520(10)
_cell_formula_units_Z            2
_cell_length_a                   5.8350(4)
_cell_length_b                   8.6412(6)
_cell_length_c                   15.4578(10)
_cell_measurement_reflns_used    5082
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.12
_cell_measurement_theta_min      2.37
_cell_volume                     771.32(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7421
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.367
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.508
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       Needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+0.2500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1066
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2461
_reflns_number_total             2701
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7nj03025h2.cif
_cod_data_source_block           BD31M
_cod_database_code               7056674
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.823
_shelx_estimated_absorpt_t_max   0.951
_exptl_absorpt_special_details
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_shelx_res_checksum              31270