A new microwave-assisted thionation-heterocyclization process leading to benzo[c]thiophene-1(3H)-thione and 1H-isothiochromene-1-thione derivatives
Giofrè, Salvatore V.; Romeo, Roberto; Mancuso, Raffaella; Cicero, Nicola; Corriero, Nicola; Chiacchio, Ugo; Romeo, Giovanni; Gabriele, Bartolo; RSC Adv.  (2016) –; doi:10.1039/C6RA01329E

data_7224188
_publ_section_title
;
 A new microwave-assisted thionation-heterocyclization process leading to
 benzo[c]thiophene-1(3H)-thione and 1H-isothiochromene-1-thione
 derivatives
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA01329E
_journal_year                    2016
_chemical_formula_sum            'C15 H10 S2'
_chemical_formula_weight         254.35
_chemical_name_systematic        (Z)-3-benzylidenebenzo[c]thiophene-1(3H)-thione
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-12-14 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7002(4)
_cell_length_b                   13.2911(16)
_cell_length_c                   16.3160(17)
_cell_measurement_reflns_used    124
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     1236.1(2)
_computing_cell_refinement
'DIRAX (Duisenberg,1992; Duisenberg et al., 2003)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        'EVAL (Nonius, 2002; Duisenberg et al., 2000)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material
'WinGX (Farrugia, 2012) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2014 (Burla et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       '\f scans and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1138
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15019
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         3.786
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.402
_exptl_absorpt_correction_T_max  0.879
_exptl_absorpt_correction_T_min  0.808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 604 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0625P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1228
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                1948
_reflns_number_total             2829
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra01329e2.cif
_cod_data_source_block           shelx
_cod_database_code               7224188
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.906
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              3056