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_7157447
_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            'C22 H16 Cl N O S'
_chemical_formula_weight         377.87
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                67.938(14)
_cell_angle_beta                 81.050(14)
_cell_angle_gamma                73.602(14)
_cell_formula_units_Z            2
_cell_length_a                   9.729(5)
_cell_length_b                   9.766(5)
_cell_length_c                   10.945(6)
_cell_measurement_reflns_used    2613
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.447
_cell_measurement_theta_min      2.185
_cell_volume                     923.1(8)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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  0.1480
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            25680
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.447
_diffrn_reflns_theta_min         2.185
_exptl_absorpt_coefficient_mu    0.330
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.046(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   0.943
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3797
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.943
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0704P)^2^+0.4154P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1349
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3310
_reflns_number_total             3797
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00083c2.cif
_cod_data_source_block           I1_0m_a
_cod_depositor_comments
'Adding full bibliography for 7157446--7157448.cif.'
_cod_original_cell_volume        923.1(9)
_cod_database_code               7157447
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              80116