Temperature-Controlled Thiation of α-Cyano-β-Alkynyl Carbonyl Derivatives for De Novo Synthesis of 2-Aminothiophenes and Thieno[2,3- c]isothiazoles.
Kao, Tzu-Ting; Peng, Bo-Kai; Liang, Min-Chieh; Lee, Chia-Jui; Chen, I-Chia; Shia, Kak-Shan; Wu, Yen-Ku; The Journal of organic chemistry 83 (2018) 14688–14697; doi:10.1021/acs.joc.8b01866

data_4035668
_publ_section_title
;
 Temperature-Controlled Thiation of \a-Cyano-\b-Alkynyl Carbonyl
 Derivatives for De Novo Synthesis of 2-Aminothiophenes and Thieno[2,3-
 c]isothiazoles.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14688
_journal_page_last               14697
_journal_paper_doi               10.1021/acs.joc.8b01866
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C18 H13 N S2'
_chemical_formula_weight         307.41
_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-2014/6
_audit_update_record
;
2017-02-11 deposited with the CCDC.
2017-11-20 downloaded from the CCDC.

2018-10-11 # Formatted by publCIF
;
_cell_angle_alpha                86.119(3)
_cell_angle_beta                 83.374(2)
_cell_angle_gamma                71.079(3)
_cell_formula_units_Z            2
_cell_length_a                   8.4886(9)
_cell_length_b                   8.9588(10)
_cell_length_c                   10.1158(11)
_cell_measurement_reflns_used    3976
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.4281
_cell_measurement_theta_min      2.4045
_cell_volume                     722.48(14)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11493
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.475
_diffrn_reflns_theta_min         2.028
_exptl_absorpt_coefficient_mu    0.360
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.8446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lump
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0316
_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^)+(0.0483P)^2^+0.2987P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0871
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2539
_reflns_number_total             2971
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {7ff4b834-f81a-4f3f-a6ca-11a3cc74fa7d}
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_cod_data_source_file            jo8b01866_si_002.cif
_cod_data_source_block           mo_170128LT_0m
_cod_database_code               4035668
_shelxl_version_number           2014/6
_shelx_res_checksum              40610
_shelx_hkl_checksum              54043