Highly Z-selective synthesis of 1,3-oxathiol-2-ylidenes and 4-methylene-oxazolidine-2-thiones via atom-specific 5-exo-dig cyclization of propargyl alcohol with isothiocyanate.
Antony Savarimuthu, S.; Leo Prakash, D. G.; Augustine Thomas, S.; Gandhi, Thirumanavelan; Bera, Mrinal K.; Organic & biomolecular chemistry 18 (2020) 3552–3562; doi:10.1039/d0ob00083c

data_7157448
_publ_section_title
;
 Highly Z-selective synthesis of 1,3-oxathiol-2-ylidenes and
 4-methylene-oxazolidine-2-thiones via atom-specific 5-exo-dig cyclization
 of propargyl alcohol with isothiocyanate.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3552
_journal_page_last               3562
_journal_paper_doi               10.1039/d0ob00083c
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C17 H13 Cl2 N O S'
_chemical_formula_weight         350.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-11-15 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.066(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.656(4)
_cell_length_b                   21.804(10)
_cell_length_c                   10.011(5)
_cell_measurement_reflns_used    2613
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.461
_cell_measurement_theta_min      2.314
_cell_volume                     1605.9(14)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1799
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            44307
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.461
_diffrn_reflns_theta_min         2.314
_exptl_absorpt_coefficient_mu    0.534
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.040(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.657
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.657
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0538
_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^)+(0.1715P)^2^+2.5619P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1571
_refine_ls_wR_factor_ref         0.1703
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2960
_reflns_number_total             3312
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00083c2.cif
_cod_data_source_block           MKB_F_2_0m_a
_cod_depositor_comments
'Adding full bibliography for 7157446--7157448.cif.'
_cod_original_cell_volume        1605.9(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7157448
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              51630