Synthesis of π-extended thiadiazole (oxides) and their electronic properties.
Linder, Thomas; Badiola, Eider; Baumgartner, Thomas; Sutherland, Todd C.; Organic letters 12 (2010) 4520–4523; doi:10.1021/ol1018213

data_1503215
_publ_section_title
;
 Synthesis of \p-extended thiadiazole (oxides) and their electronic
 properties.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              4520
_journal_page_last               4523
_journal_paper_doi               10.1021/ol1018213
_journal_volume                  12
_journal_year                    2010
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C16 H8 N2 O S'
_chemical_formula_sum            'C16 H8 N2 O S'
_chemical_formula_weight         276.3
_chemical_name_common            EB038
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-02-12T15:24:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 115.9130(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6637(4)
_cell_length_b                   11.9040(3)
_cell_length_c                   7.2169(2)
_cell_measurement_reflns_used    2701
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      67.04
_cell_measurement_theta_min      5
_cell_volume                     1133.10(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4284
_diffrn_reflns_theta_full        67.76
_diffrn_reflns_theta_max         67.76
_diffrn_reflns_theta_min         5
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.494
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.5808
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS-2008 (Bruker)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.62
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.28
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.12
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         1013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.12
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0656P)^2^+0.3835P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1004
_reflns_number_gt                943
_reflns_number_total             1013
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol1018213_si_002.cif
_cod_data_source_block           PyrSO
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1503215