#------------------------------------------------------------------------------
#$Date: 2022-03-07 11:31:52 +0200 (Mon, 07 Mar 2022) $
#$Revision: 273492 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/46/8104664.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8104664
loop_
_publ_author_name
'Xin, Nana'
'Zheng, Jun'
'He, Qingpeng'
_publ_section_title
;
 The crystal structure of
 N,N′-(Disulfanediyldi-2,1-phenylene)di(6′-methylpyridine)-2-carboxamide,
 C26H22N4O2S2
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1055
_journal_page_last               1057
_journal_paper_doi               10.1515/ncrs-2021-0206
_journal_volume                  236
_journal_year                    2021
_chemical_formula_sum            'C26 H22 N4 O2 S2'
_chemical_formula_weight         486.59
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                81.433(2)
_cell_angle_beta                 76.5360(10)
_cell_angle_gamma                82.641(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9495(7)
_cell_length_b                   11.2494(12)
_cell_length_c                   13.7829(13)
_cell_measurement_reflns_used    1575
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.839
_cell_measurement_theta_min      2.244
_cell_volume                     1179.7(2)
_computing_cell_refinement       'SMART [1]'
_computing_data_collection       'SMART [1]'
_computing_data_reduction        'SMART [1]'
_computing_molecular_graphics    'XP in SHELXTL [2]'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018) [2]'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018) [2]'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_av_unetI/netI     0.0798
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6008
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.020
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         2.243
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4109
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.1145
_refine_ls_R_factor_gt           0.0727
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1229P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1960
_refine_ls_wR_factor_ref         0.2189
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2424
_reflns_number_total             4109
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0206_suppl.cif
_cod_data_source_block           Xin
_cod_database_code               8104664
_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   0.943
_shelx_estimated_absorpt_t_max   0.950
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7177(5) 0.7664(3) 0.2043(3) 0.0588(10) Uani 1 1 d . . . . .
H1 H 0.670456 0.716123 0.253320 0.071 Uiso 1 1 calc R U . . .
N2 N 0.6380(6) 0.5491(4) 0.2069(3) 0.0718(12) Uani 1 1 d . . . . .
N3 N 1.0316(5) 0.7030(3) 0.3478(2) 0.0538(9) Uani 1 1 d . . . . .
H3' H 0.997609 0.753084 0.391490 0.065 Uiso 1 1 calc R U . . .
N4 N 1.1458(5) 0.9091(3) 0.3548(3) 0.0614(10) Uani 1 1 d . . . . .
O1 O 0.8270(7) 0.7863(4) 0.0357(3) 0.1122(16) Uani 1 1 d . U . . .
O2 O 1.2059(5) 0.6831(3) 0.1943(3) 0.0941(13) Uani 1 1 d . . . . .
S1 S 0.54357(15) 0.79815(11) 0.41849(8) 0.0582(4) Uani 1 1 d . . . . .
S2 S 0.70671(16) 0.71049(10) 0.51002(8) 0.0572(4) Uani 1 1 d . . . . .
C1 C 0.6675(6) 0.9025(4) 0.3295(3) 0.0534(11) Uani 1 1 d . . . . .
C2 C 0.6883(7) 1.0132(4) 0.3573(4) 0.0672(13) Uani 1 1 d . . . . .
H2 H 0.643264 1.029291 0.423095 0.081 Uiso 1 1 calc R U . . .
C3 C 0.7743(7) 1.0987(5) 0.2886(4) 0.0756(15) Uani 1 1 d . . . . .
H3 H 0.785486 1.172740 0.307529 0.091 Uiso 1 1 calc R U . . .
C4 C 0.8438(7) 1.0744(5) 0.1919(4) 0.0714(14) Uani 1 1 d . . . . .
H4 H 0.902745 1.132176 0.145583 0.086 Uiso 1 1 calc R U . . .
C5 C 0.8274(6) 0.9656(4) 0.1626(3) 0.0609(12) Uani 1 1 d . . . . .
H5 H 0.875053 0.950463 0.096787 0.073 Uiso 1 1 calc R U . . .
C6 C 0.7399(6) 0.8781(4) 0.2308(3) 0.0510(11) Uani 1 1 d . . . . .
C7 C 0.7597(7) 0.7257(5) 0.1128(4) 0.0683(13) Uani 1 1 d . . . . .
C8 C 0.7114(7) 0.6009(4) 0.1161(4) 0.0624(12) Uani 1 1 d . . . . .
C9 C 0.7419(7) 0.5429(5) 0.0286(4) 0.0732(14) Uani 1 1 d . . . . .
C10 C 0.6893(9) 0.4266(6) 0.0439(5) 0.0928(19) Uani 1 1 d . . . . .
H10 H 0.706046 0.384018 -0.011033 0.111 Uiso 1 1 calc R U . . .
C11 C 0.6149(9) 0.3740(6) 0.1356(6) 0.097(2) Uani 1 1 d . . . . .
H11 H 0.580265 0.296503 0.144218 0.116 Uiso 1 1 calc R U . . .
C12 C 0.5915(8) 0.4382(5) 0.2167(4) 0.0835(16) Uani 1 1 d . . . . .
H12 H 0.541239 0.402251 0.280347 0.100 Uiso 1 1 calc R U . . .
C13 C 0.8273(10) 0.5978(6) -0.0750(4) 0.110(2) Uani 1 1 d . . . . .
H13A H 0.831778 0.542691 -0.122594 0.165 Uiso 1 1 calc R U . . .
H13B H 0.943163 0.613764 -0.075150 0.165 Uiso 1 1 calc R U . . .
H13C H 0.761290 0.672054 -0.093152 0.165 Uiso 1 1 calc R U . . .
C14 C 0.8085(6) 0.5824(4) 0.4495(3) 0.0490(10) Uani 1 1 d . . . . .
C15 C 0.7402(6) 0.4719(4) 0.4800(3) 0.0575(12) Uani 1 1 d . . . . .
H15 H 0.641084 0.465493 0.531268 0.069 Uiso 1 1 calc R U . . .
C16 C 0.8191(7) 0.3712(4) 0.4345(4) 0.0629(12) Uani 1 1 d . . . . .
H16 H 0.775195 0.296642 0.455838 0.076 Uiso 1 1 calc R U . . .
C17 C 0.9627(6) 0.3826(4) 0.3576(4) 0.0611(12) Uani 1 1 d . . . . .
H17 H 1.012461 0.315849 0.324980 0.073 Uiso 1 1 calc R U . . .
C18 C 1.0348(6) 0.4901(4) 0.3277(3) 0.0559(11) Uani 1 1 d . . . . .
H18 H 1.134389 0.494795 0.276634 0.067 Uiso 1 1 calc R U . . .
C19 C 0.9592(6) 0.5924(4) 0.3734(3) 0.0493(10) Uani 1 1 d . . . . .
C20 C 1.1469(6) 0.7423(4) 0.2644(3) 0.0559(11) Uani 1 1 d . . . . .
C21 C 1.1947(6) 0.8672(4) 0.2649(3) 0.0527(11) Uani 1 1 d . . . . .
C22 C 1.2820(6) 0.9350(4) 0.1781(3) 0.0579(12) Uani 1 1 d . . . . .
C23 C 1.3214(6) 1.0475(5) 0.1901(4) 0.0724(14) Uani 1 1 d . . . . .
H23 H 1.379576 1.095328 0.134613 0.087 Uiso 1 1 calc R U . . .
C24 C 1.2765(7) 1.0902(4) 0.2820(4) 0.0715(14) Uani 1 1 d . . . . .
H24 H 1.305139 1.165410 0.289570 0.086 Uiso 1 1 calc R U . . .
C25 C 1.1884(7) 1.0185(4) 0.3621(4) 0.0673(13) Uani 1 1 d . . . . .
H25 H 1.156608 1.047116 0.424353 0.081 Uiso 1 1 calc R U . . .
C26 C 1.3245(8) 0.8923(5) 0.0747(4) 0.0847(17) Uani 1 1 d . . . . .
H26A H 1.414779 0.826687 0.072271 0.127 Uiso 1 1 calc R U . . .
H26B H 1.362995 0.957700 0.024447 0.127 Uiso 1 1 calc R U . . .
H26C H 1.222498 0.865556 0.062098 0.127 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C7 N1 C6 129.7(4) . .
C12 N2 C8 119.2(5) . .
C20 N3 C19 129.3(4) . .
C25 N4 C21 118.3(4) . .
C1 S1 S2 106.32(15) . .
C14 S2 S1 104.29(14) . .
C2 C1 C6 119.0(4) . .
C2 C1 S1 119.4(4) . .
C6 C1 S1 121.5(3) . .
C3 C2 C1 120.8(5) . .
C2 C3 C4 119.7(5) . .
C3 C4 C5 120.8(5) . .
C4 C5 C6 120.4(5) . .
C5 C6 N1 122.6(4) . .
C5 C6 C1 119.2(4) . .
N1 C6 C1 118.2(4) . .
O1 C7 N1 123.1(5) . .
O1 C7 C8 123.7(4) . .
N1 C7 C8 113.1(4) . .
N2 C8 C9 122.9(5) . .
N2 C8 C7 115.2(4) . .
C9 C8 C7 121.9(5) . .
C10 C9 C8 115.1(5) . .
C10 C9 C13 120.5(5) . .
C8 C9 C13 124.4(5) . .
C11 C10 C9 122.2(6) . .
C10 C11 C12 118.3(6) . .
N2 C12 C11 122.4(6) . .
C15 C14 C19 120.2(4) . .
C15 C14 S2 119.6(3) . .
C19 C14 S2 120.2(3) . .
C16 C15 C14 120.2(4) . .
C17 C16 C15 119.2(4) . .
C16 C17 C18 121.6(4) . .
C17 C18 C19 120.2(4) . .
C18 C19 C14 118.4(4) . .
C18 C19 N3 122.3(4) . .
C14 C19 N3 119.3(4) . .
O2 C20 N3 123.6(4) . .
O2 C20 C21 122.9(4) . .
N3 C20 C21 113.5(4) . .
N4 C21 C22 122.8(4) . .
N4 C21 C20 114.7(4) . .
C22 C21 C20 122.5(4) . .
C23 C22 C21 116.3(5) . .
C23 C22 C26 120.7(4) . .
C21 C22 C26 123.0(4) . .
C24 C23 C22 121.6(5) . .
C25 C24 C23 117.9(5) . .
N4 C25 C24 123.1(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C7 1.360(6) .
N1 C6 1.402(5) .
N2 C12 1.325(7) .
N2 C8 1.333(6) .
N3 C20 1.348(5) .
N3 C19 1.401(5) .
N4 C25 1.342(6) .
N4 C21 1.345(6) .
O1 C7 1.222(6) .
O2 C20 1.224(5) .
S1 C1 1.776(5) .
S1 S2 2.0758(17) .
S2 C14 1.781(4) .
C1 C2 1.396(6) .
C1 C6 1.402(6) .
C2 C3 1.372(7) .
C3 C4 1.373(7) .
C4 C5 1.375(7) .
C5 C6 1.389(6) .
C7 C8 1.494(7) .
C8 C9 1.413(7) .
C9 C10 1.396(8) .
C9 C13 1.508(8) .
C10 C11 1.348(9) .
C11 C12 1.383(8) .
C14 C15 1.389(6) .
C14 C19 1.401(6) .
C15 C16 1.385(6) .
C16 C17 1.369(6) .
C17 C18 1.371(6) .
C18 C19 1.395(6) .
C20 C21 1.503(6) .
C21 C22 1.405(6) .
C22 C23 1.383(7) .
C22 C26 1.521(7) .
C23 C24 1.375(7) .
C24 C25 1.371(7) .
