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_1503212
_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         'C14 H8 N2 S1'
_chemical_formula_sum            'C14 H8 N2 S'
_chemical_formula_weight         236.28
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-06-16T16:14:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 92.86(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.80450(10)
_cell_length_b                   14.6240(4)
_cell_length_c                   18.5827(5)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_measurement_wavelength     0.71073
_cell_volume                     1032.60(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Diamond 3.11'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.913
_diffrn_measured_fraction_theta_max 0.913
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1202
_diffrn_reflns_av_unetI/netI     0.1334
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10513
_diffrn_reflns_theta_full        69.13
_diffrn_reflns_theta_max         69.13
_diffrn_reflns_theta_min         3.85
_exptl_absorpt_coefficient_mu    2.549
_exptl_absorpt_correction_T_max  0.784
_exptl_absorpt_correction_T_min  0.693
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'HKL Scalepack'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.52
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.108
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.803
_refine_diff_density_rms         0.147
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.1525
_refine_ls_R_factor_gt           0.0672
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1645P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1888
_refine_ls_wR_factor_ref         0.2657
_reflns_number_gt                1067
_reflns_number_total             1770
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol1018213_si_002.cif
_cod_data_source_block           PhenS
_cod_original_cell_volume        1032.59(5)
_cod_original_sg_symbol_H-M      P21/n
_cod_original_formula_sum        'C14 H8 N2 S1'
_cod_database_code               1503212