Straightforward chemoselective access to unsymmetrical dithioacetals through a thiosulfonate homologation-nucleophilic substitution sequence.
Ielo, Laura; Pillari, Veronica; Gajic, Natalie; Holzer, Wolfgang; Pace, Vittorio; Chemical communications (Cambridge, England) 56 (2020) 12395–12398; doi:10.1039/d0cc04896h

data_7127183
_publ_section_title
;
 Straightforward chemoselective access to unsymmetrical dithioacetals
 through a thiosulfonate homologation-nucleophilic substitution sequence.
;
_journal_issue                   82
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12395
_journal_page_last               12398
_journal_paper_doi               10.1039/d0cc04896h
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H11 N O S2'
_chemical_formula_sum            'C14 H11 N O S2'
_chemical_formula_weight         273.36
_chemical_name_systematic
2-{[(Phenylsulfanyl)methyl]sulfanyl}-1,3-benzoxazole
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-07-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-15 deposited with the CCDC.	2020-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.436(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5155(11)
_cell_length_b                   4.8412(4)
_cell_length_c                   13.9736(18)
_cell_measurement_reflns_used    6653
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.005
_cell_measurement_theta_min      2.466
_cell_volume                     639.66(12)
_computing_cell_refinement       'SAINT V8.38A (2016)'
_computing_data_collection       APEX3
_computing_data_reduction        'SAINT V8.38A (2016)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15673
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.084
_diffrn_reflns_theta_min         2.466
_diffrn_source                   'Sealed xray tube'
_diffrn_source_type              'Incoatec IuS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.401
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.7062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0491 before and 0.0412 after correction. 
The Ratio of minimum to maximum transmission is 0.9008. 
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.045
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1347 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3715
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0303
_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^)+(0.0109P)^2^+0.3131P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0555
_refine_ls_wR_factor_ref         0.0680
_reflns_Friedel_coverage         0.782
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                3340
_reflns_number_total             3715
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04896h2.cif
_cod_data_source_block           mo_vipa_dk_15_3_p21
_cod_depositor_comments
'Adding full bibliography for 7127182--7127184.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7127183
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.982