2,2'-[Methylenebis(sulfanediyl)]bis(pyridine 1-oxide)
Siegel, David J.; Howarth, Alexis N.; Traver, Joseph R.; Hillesheim, Patrick C.; Zeller, Matthias; Mirjafari, Arsalan; IUCrData 5 (2020) x200171–; doi:10.1107/S2414314620001716

data_1557304
_publ_section_title
;
 2,2'-[Methylenebis(sulfanediyl)]bis(pyridine 1-oxide)
;
_journal_coeditor_code           BV4026
_journal_issue                   2
_journal_name_full               IUCrData
_journal_page_first              x200171
_journal_paper_doi               10.1107/S2414314620001716
_journal_volume                  5
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C11 H10 N2 O2 S2'
_chemical_formula_moiety         'C11 H10 N2 O2 S2'
_chemical_formula_sum            'C11 H10 N2 O2 S2'
_chemical_formula_weight         266.33
_chemical_name_systematic
;
2,2'-[Methylenebis(sulfanediyl)]bis(pyridine 1-oxide)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 95.958(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.1658(2)
_cell_length_b                   10.4706(6)
_cell_length_c                   12.7624(7)
_cell_measurement_reflns_used    9929
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.2838
_cell_measurement_theta_min      2.5217
_cell_volume                     553.67(5)
_computing_cell_refinement
;
SAINT (Bruker, 2018)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2018)
;
_computing_molecular_graphics
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009) and
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009),
publCIF (Westrip, 2010) and
enCIFer (Allen <i>et al.</i>,  2004)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015, 2018),
<i>SHELXLE</i> (H\"ubschle <i>et al.</i>,  2011) and
PLATON (Spek, 2020)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17033
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.297
_diffrn_reflns_theta_min         2.522
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    0.470
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.5277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.483
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1650 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         4262
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0424P)^2^+0.1658P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1002
_reflns_number_gt                3794
_reflns_number_total             4262
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            bv4026sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1557304
_cod_database_fobs_code          1557304
_shelx_estimated_absorpt_t_min   0.782
_shelx_estimated_absorpt_t_max   0.981
_shelx_hkl_checksum              99266
_shelx_res_checksum              90924