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_1503216
_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 O2 S1'
_chemical_formula_sum            'C16 H8 N2 O2 S'
_chemical_formula_weight         292.31
_chemical_name_common            pyrSO2
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-06-16T17:03:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.00
_cell_angle_beta                 102.500(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4588(6)
_cell_length_b                   15.8146(6)
_cell_length_c                   6.8807(3)
_cell_measurement_reflns_used    5079
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1217.34(10)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.0015337
_diffrn_orient_matrix_UB_12      0.0874307
_diffrn_orient_matrix_UB_13      -0.0017584
_diffrn_orient_matrix_UB_21      0.1459583
_diffrn_orient_matrix_UB_22      -0.0185607
_diffrn_orient_matrix_UB_23      -0.0124109
_diffrn_orient_matrix_UB_31      -0.0292221
_diffrn_orient_matrix_UB_32      0.0012622
_diffrn_orient_matrix_UB_33      -0.0619778
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.1165
_diffrn_reflns_av_unetI/netI     0.0771
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9876
_diffrn_reflns_theta_full        27.58
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  0.9973
_exptl_absorpt_correction_T_min  0.9786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV: (Blessing, 1997)'
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.025
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.23
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.23
_refine_ls_R_factor_all          0.1479
_refine_ls_R_factor_gt           0.1121
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1360P)^2^+4.5147P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3073
_refine_ls_wR_factor_ref         0.3323
_reflns_number_gt                2071
_reflns_number_total             2805
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol1018213_si_002.cif
_cod_data_source_block           PyrSO2
_cod_original_cell_volume        1217.34(9)
_cod_original_sg_symbol_Hall     '-P2 ybc'
_cod_original_sg_symbol_H-M      P21/c
_cod_original_formula_sum        'C16 H8 N2 O2 S1'
_cod_database_code               1503216