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_7157446
_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_moiety         'C17 H15 N O2 S'
_chemical_formula_sum            'C17 H15 N O2 S'
_chemical_formula_weight         297.36
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-12-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-10-02 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.118(5)
_cell_angle_beta                 98.358(4)
_cell_angle_gamma                94.483(4)
_cell_formula_units_Z            2
_cell_length_a                   7.3519(9)
_cell_length_b                   7.7182(12)
_cell_length_c                   13.473(2)
_cell_measurement_reflns_used    2755
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.552
_cell_measurement_theta_min      2.647
_cell_volume                     754.00(19)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_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            10806
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.375
_diffrn_reflns_theta_min         2.809
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0722 before and 0.0379 after correction. The Ratio of minimum to maximum transmission is 0.9473. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         4010
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0447P)^2^+0.0730P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1158
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2154
_reflns_number_total             4010
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00083c2.cif
_cod_data_source_block           d1
_cod_depositor_comments
'Adding full bibliography for 7157446--7157448.cif.'
_cod_original_cell_volume        753.98(19)
_cod_database_code               7157446
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.958
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C17(H17), C15(H15), C14(H14), C13(H13),
 C16(H16)
;
_shelx_res_checksum              3107
_olex2_submission_special_instructions 'No special instructions were received'