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_1503213
_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 O2 S1 '
_chemical_formula_sum            'C14 H8 N2 O2 S'
_chemical_formula_weight         268.294
_chemical_name_common            phenSO2
_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             2010-03-07T11:56:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 112.64(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9578(4)
_cell_length_b                   17.0550(8)
_cell_length_c                   10.1330(8)
_cell_measurement_reflns_used    2049
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.998
_cell_volume                     1109.8(4)
_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 0.974
_diffrn_measured_fraction_theta_max 0.974
_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      -0.0581338
_diffrn_orient_matrix_UB_12      -0.0489771
_diffrn_orient_matrix_UB_13      0.0271691
_diffrn_orient_matrix_UB_21      -0.0274289
_diffrn_orient_matrix_UB_22      -0.0204674
_diffrn_orient_matrix_UB_23      -0.0994656
_diffrn_orient_matrix_UB_31      0.1368654
_diffrn_orient_matrix_UB_32      -0.0249049
_diffrn_orient_matrix_UB_33      0.0283133
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4250
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_correction_T_min  0.9525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2568
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.166
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0858P)^2^+0.9091P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1596
_reflns_number_gt                2310
_reflns_number_total             2568
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol1018213_si_002.cif
_cod_data_source_block           PhenSO2
_cod_original_sg_symbol_H-M      P21/c
_cod_original_formula_sum        'C14 H8 N2 O2 S1'
_cod_database_code               1503213