#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/73/1557304.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1557304
loop_
_publ_author_name
'Siegel, David J.'
'Howarth, Alexis N.'
'Traver, Joseph R.'
'Hillesheim, Patrick C.'
'Zeller, Matthias'
'Mirjafari, Arsalan'
_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
;
OLEX2 (Dolomanov et al.,  2009) and
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009),
publCIF (Westrip, 2010) and
enCIFer (Allen et al.,  2004)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015, 2018),
SHELXLE (Hübschle et al.,  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 et al.,  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 x determined using 1650 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  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/[σ²(Fo²)+(0.0424P)²+0.1658P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.782
_shelx_estimated_absorpt_t_max   0.981
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
S S1 0.81710(15) 0.68956(6) 0.58939(4) 0.01584(13) Uani d 1
S S2 0.86177(15) 0.83538(6) 0.79102(4) 0.01541(13) Uani d 1
O O1 0.8980(5) 0.5371(2) 0.42557(17) 0.0230(4) Uani d 1
O O2 1.0430(5) 0.7815(2) 0.99221(16) 0.0224(4) Uani d 1
N N1 0.7052(5) 0.6307(2) 0.39242(17) 0.0162(4) Uani d 1
N N2 0.8365(5) 0.6943(2) 0.95562(16) 0.0162(4) Uani d 1
C C1 0.6300(6) 0.7213(2) 0.46299(19) 0.0152(4) Uani d 1
C C2 0.4276(6) 0.8217(3) 0.43009(19) 0.0178(5) Uani d 1
H H2 0.373352 0.884463 0.479079 0.021 Uiso calc 1
C C3 0.3049(7) 0.8300(3) 0.3252(2) 0.0221(5) Uani d 1
H H3 0.167937 0.899069 0.301822 0.026 Uiso calc 1
C C4 0.3825(8) 0.7369(3) 0.2540(2) 0.0241(6) Uani d 1
H H4 0.299597 0.741896 0.181928 0.029 Uiso calc 1
C C5 0.5806(8) 0.6380(3) 0.2897(2) 0.0225(5) Uani d 1
H H5 0.631713 0.573381 0.241816 0.027 Uiso calc 1
C C6 0.7073(6) 0.7022(3) 0.85309(18) 0.0139(4) Uani d 1
C C7 0.4827(6) 0.6128(3) 0.8125(2) 0.0169(5) Uani d 1
H H7 0.391355 0.618626 0.741250 0.020 Uiso calc 1
C C8 0.3922(7) 0.5152(3) 0.8762(2) 0.0197(5) Uani d 1
H H8 0.236511 0.454000 0.849241 0.024 Uiso calc 1
C C9 0.5303(7) 0.5072(3) 0.9797(2) 0.0223(5) Uani d 1
H H9 0.471354 0.440113 1.024029 0.027 Uiso calc 1
C C10 0.7527(7) 0.5969(3) 1.0173(2) 0.0209(5) Uani d 1
H H10 0.849794 0.590692 1.087870 0.025 Uiso calc 1
C C11 0.6603(6) 0.8234(3) 0.65943(18) 0.0150(4) Uani d 1
H H11A 0.692061 0.903548 0.620641 0.018 Uiso calc 1
H H11B 0.425731 0.811823 0.662873 0.018 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 S1 C11 99.12(11)
C6 S2 C11 102.00(12)
O1 N1 C5 120.8(2)
O1 N1 C1 118.8(2)
C5 N1 C1 120.4(2)
O2 N2 C10 121.2(2)
O2 N2 C6 118.6(2)
C10 N2 C6 120.2(2)
N1 C1 C2 120.1(2)
N1 C1 S1 111.44(18)
C2 C1 S1 128.50(19)
C3 C2 C1 119.5(2)
C3 C2 H2 120.3
C1 C2 H2 120.3
C2 C3 C4 120.0(3)
C2 C3 H3 120.0
C4 C3 H3 120.0
C5 C4 C3 119.0(3)
C5 C4 H4 120.5
C3 C4 H4 120.5
N1 C5 C4 121.2(3)
N1 C5 H5 119.4
C4 C5 H5 119.4
N2 C6 C7 120.1(2)
N2 C6 S2 110.72(19)
C7 C6 S2 129.16(18)
C8 C7 C6 119.6(2)
C8 C7 H7 120.2
C6 C7 H7 120.2
C7 C8 C9 119.5(3)
C7 C8 H8 120.2
C9 C8 H8 120.2
C10 C9 C8 119.4(3)
C10 C9 H9 120.3
C8 C9 H9 120.3
N2 C10 C9 121.1(2)
N2 C10 H10 119.4
C9 C10 H10 119.4
S2 C11 S1 110.79(14)
S2 C11 H11A 109.5
S1 C11 H11A 109.5
S2 C11 H11B 109.5
S1 C11 H11B 109.5
H11A C11 H11B 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.749(3)
S1 C11 1.820(3)
S2 C6 1.759(3)
S2 C11 1.802(2)
O1 N1 1.309(3)
O2 N2 1.307(3)
N1 C5 1.361(3)
N1 C1 1.366(3)
N2 C10 1.356(3)
N2 C6 1.365(3)
C1 C2 1.386(4)
C2 C3 1.385(3)
C2 H2 0.9500
C3 C4 1.393(4)
C3 H3 0.9500
C4 C5 1.373(4)
C4 H4 0.9500
C5 H5 0.9500
C6 C7 1.385(4)
C7 C8 1.383(4)
C7 H7 0.9500
C8 C9 1.388(4)
C8 H8 0.9500
C9 C10 1.371(4)
C9 H9 0.9500
C10 H10 0.9500
C11 H11A 0.9900
C11 H11B 0.9900
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H2 O1 2_656 0.95 2.37 3.292(3) 164.6 yes
C9 H9 O2 2_647 0.95 2.70 3.405(4) 131.4 yes
C11 H11A O1 2_756 0.99 2.33 3.159(3) 140.8 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 N1 C1 C2 179.7(2)
C5 N1 C1 C2 -0.4(4)
O1 N1 C1 S1 -0.4(3)
C5 N1 C1 S1 179.46(19)
C11 S1 C1 N1 -179.00(19)
C11 S1 C1 C2 0.9(3)
N1 C1 C2 C3 -0.5(4)
S1 C1 C2 C3 179.6(2)
C1 C2 C3 C4 0.7(4)
C2 C3 C4 C5 0.1(4)
O1 N1 C5 C4 -179.0(3)
C1 N1 C5 C4 1.2(4)
C3 C4 C5 N1 -1.0(4)
O2 N2 C6 C7 -178.7(2)
C10 N2 C6 C7 1.9(3)
O2 N2 C6 S2 0.4(3)
C10 N2 C6 S2 -179.0(2)
C11 S2 C6 N2 179.53(17)
C11 S2 C6 C7 -1.5(3)
N2 C6 C7 C8 -0.5(4)
S2 C6 C7 C8 -179.4(2)
C6 C7 C8 C9 -0.7(4)
C7 C8 C9 C10 0.5(4)
O2 N2 C10 C9 178.4(3)
C6 N2 C10 C9 -2.2(4)
C8 C9 C10 N2 0.9(4)
C6 S2 C11 S1 -71.09(14)
C1 S1 C11 S2 -170.31(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306128
