#------------------------------------------------------------------------------
#$Date: 2023-03-08 11:53:58 +0200 (Wed, 08 Mar 2023) $
#$Revision: 281738 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/68/8106881.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_8106881
loop_
_publ_author_name
'Wang, Zhi-Peng'
'Zhang, Fan'
'Zhang, Qi-Qi'
'Sun, Xin-Zhan'
_publ_section_title
;
 Crystal structure of succinic acid ---
 4-((pyridin-4-ylmethyl)sulfanylpyridine (1/1), C15H16N2O4S
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              383
_journal_page_last               384
_journal_paper_doi               10.1515/ncrs-2014-9122
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C15 H16 N2 O4 S'
_chemical_formula_weight         320.36
_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                109.491(5)
_cell_angle_beta                 100.496(5)
_cell_angle_gamma                107.860(5)
_cell_formula_units_Z            2
_cell_length_a                   7.3024(6)
_cell_length_b                   10.7115(7)
_cell_length_c                   11.2743(6)
_cell_measurement_temperature    296(2)
_cell_volume                     750.44(10)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Apex II Area Dector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_unetI/netI     0.0802
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10790
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.197
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       Block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2947
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.1358
_refine_ls_R_factor_gt           0.0691
_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)+(0.0947P)²+0.0753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1739
_refine_ls_wR_factor_ref         0.2136
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1569
_reflns_number_total             2947
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2014-9122_suppl.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_cell_volume        750.44(9)
_cod_database_code               8106881
_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.
;
_shelxl_version_number           2014-3
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
S1 S 0.68243(17) 0.39601(11) 0.96789(10) 0.0642(4) Uani 1 1 d . . . . .
N1 N 0.4520(5) 0.1980(4) 0.4477(3) 0.0592(9) Uani 1 1 d . . . . .
N2 N 0.9786(5) 0.7361(3) 1.3892(3) 0.0517(8) Uani 1 1 d . . . . .
O1 O 0.1284(4) -0.0738(3) -0.3638(2) 0.0729(9) Uani 1 1 d . . . . .
H1B H 0.0801 -0.1402 -0.4381 0.109 Uiso 1 1 calc R U . . .
O2 O 0.0612(5) -0.2531(3) -0.3013(3) 0.0801(10) Uani 1 1 d . . . . .
O3 O 0.3669(5) 0.1803(3) 0.1315(3) 0.0876(11) Uani 1 1 d . . . . .
O4 O 0.3002(5) 0.0059(3) 0.1993(3) 0.0781(10) Uani 1 1 d . . . . .
H4B H 0.3500 0.0738 0.2726 0.117 Uiso 1 1 calc R U . . .
C1 C 0.9795(6) 0.7748(4) 1.2907(4) 0.0574(11) Uani 1 1 d . . . . .
H1A H 1.0421 0.8725 1.3110 0.069 Uiso 1 1 calc R U . . .
C2 C 0.8928(6) 0.6790(4) 1.1577(4) 0.0527(10) Uani 1 1 d . . . . .
H2A H 0.8983 0.7118 1.0912 0.063 Uiso 1 1 calc R U . . .
C3 C 0.7981(5) 0.5339(4) 1.1268(3) 0.0418(9) Uani 1 1 d . . . . .
C4 C 0.7977(6) 0.4918(4) 1.2308(4) 0.0545(10) Uani 1 1 d . . . . .
H4A H 0.7357 0.3949 1.2138 0.065 Uiso 1 1 calc R U . . .
C5 C 0.8894(6) 0.5943(4) 1.3584(4) 0.0556(11) Uani 1 1 d . . . . .
H5A H 0.8903 0.5647 1.4271 0.067 Uiso 1 1 calc R U . . .
C6 C 0.7154(5) 0.4943(4) 0.8619(3) 0.0391(8) Uani 1 1 d . . . . .
H6A H 0.6506 0.5621 0.8799 0.047 Uiso 1 1 calc R U . . .
H6B H 0.8586 0.5477 0.8796 0.047 Uiso 1 1 calc R U . . .
C7 C 0.6190(5) 0.3841(4) 0.7170(3) 0.0428(9) Uani 1 1 d . . . . .
C8 C 0.6498(6) 0.4326(4) 0.6206(4) 0.0623(12) Uani 1 1 d . . . . .
H8A H 0.7279 0.5291 0.6442 0.075 Uiso 1 1 calc R U . . .
C9 C 0.5640(6) 0.3369(5) 0.4885(4) 0.0686(13) Uani 1 1 d . . . . .
H9A H 0.5859 0.3719 0.4249 0.082 Uiso 1 1 calc R U . . .
C10 C 0.4234(6) 0.1523(4) 0.5406(4) 0.0656(12) Uani 1 1 d . . . . .
H10A H 0.3444 0.0553 0.5142 0.079 Uiso 1 1 calc R U . . .
C11 C 0.5031(6) 0.2395(4) 0.6737(4) 0.0603(11) Uani 1 1 d . . . . .
H11A H 0.4790 0.2009 0.7348 0.072 Uiso 1 1 calc R U . . .
C12 C 0.3020(5) 0.0547(4) 0.1077(3) 0.0509(10) Uani 1 1 d . . . . .
C13 C 0.2124(6) -0.0651(4) -0.0303(3) 0.0504(10) Uani 1 1 d . . . . .
H13A H 0.2891 -0.1254 -0.0391 0.060 Uiso 1 1 calc R U . . .
H13B H 0.0739 -0.1245 -0.0427 0.060 Uiso 1 1 calc R U . . .
C14 C 0.2130(6) -0.0098(4) -0.1371(3) 0.0515(10) Uani 1 1 d . . . . .
H14A H 0.1358 0.0502 -0.1280 0.062 Uiso 1 1 calc R U . . .
H14B H 0.3515 0.0504 -0.1237 0.062 Uiso 1 1 calc R U . . .
C15 C 0.1263(5) -0.1261(4) -0.2748(3) 0.0480(10) Uani 1 1 d . . . . .
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
C3 S1 C6 102.64(17) . .
C10 N1 C9 116.6(3) . .
C1 N2 C5 117.3(3) . .
C15 O1 H1B 109.5 . .
C12 O4 H4B 109.5 . .
N2 C1 C2 124.1(4) . .
N2 C1 H1A 118.0 . .
C2 C1 H1A 118.0 . .
C3 C2 C1 118.3(4) . .
C3 C2 H2A 120.8 . .
C1 C2 H2A 120.8 . .
C2 C3 C4 118.0(3) . .
C2 C3 S1 125.9(3) . .
C4 C3 S1 116.1(3) . .
C5 C4 C3 119.2(3) . .
C5 C4 H4A 120.4 . .
C3 C4 H4A 120.4 . .
N2 C5 C4 123.1(3) . .
N2 C5 H5A 118.5 . .
C4 C5 H5A 118.5 . .
C7 C6 S1 108.1(2) . .
C7 C6 H6A 110.1 . .
S1 C6 H6A 110.1 . .
C7 C6 H6B 110.1 . .
S1 C6 H6B 110.1 . .
H6A C6 H6B 108.4 . .
C11 C7 C8 116.5(3) . .
C11 C7 C6 125.8(3) . .
C8 C7 C6 117.7(3) . .
C7 C8 C9 119.6(4) . .
C7 C8 H8A 120.2 . .
C9 C8 H8A 120.2 . .
N1 C9 C8 123.5(4) . .
N1 C9 H9A 118.3 . .
C8 C9 H9A 118.3 . .
N1 C10 C11 123.8(4) . .
N1 C10 H10A 118.1 . .
C11 C10 H10A 118.1 . .
C10 C11 C7 120.0(4) . .
C10 C11 H11A 120.0 . .
C7 C11 H11A 120.0 . .
O3 C12 O4 123.3(3) . .
O3 C12 C13 124.4(3) . .
O4 C12 C13 112.3(3) . .
C14 C13 C12 112.8(3) . .
C14 C13 H13A 109.0 . .
C12 C13 H13A 109.0 . .
C14 C13 H13B 109.0 . .
C12 C13 H13B 109.0 . .
H13A C13 H13B 107.8 . .
C15 C14 C13 114.0(3) . .
C15 C14 H14A 108.8 . .
C13 C14 H14A 108.8 . .
C15 C14 H14B 108.8 . .
C13 C14 H14B 108.8 . .
H14A C14 H14B 107.7 . .
O2 C15 O1 123.7(3) . .
O2 C15 C14 124.4(3) . .
O1 C15 C14 111.9(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C3 1.738(3) .
S1 C6 1.840(3) .
N1 C10 1.319(5) .
N1 C9 1.324(5) .
N2 C1 1.309(5) .
N2 C5 1.346(5) .
O1 C15 1.302(4) .
O1 H1B 0.8200 .
O2 C15 1.203(4) .
O3 C12 1.195(4) .
O4 C12 1.305(4) .
O4 H4B 0.8200 .
C1 C2 1.389(5) .
C1 H1A 0.9300 .
C2 C3 1.382(5) .
C2 H2A 0.9300 .
C3 C4 1.390(5) .
C4 C5 1.366(5) .
C4 H4A 0.9300 .
C5 H5A 0.9300 .
C6 C7 1.530(4) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C11 1.376(5) .
C7 C8 1.378(5) .
C8 C9 1.381(5) .
C8 H8A 0.9300 .
C9 H9A 0.9300 .
C10 C11 1.369(5) .
C10 H10A 0.9300 .
C11 H11A 0.9300 .
C12 C13 1.509(5) .
C13 C14 1.509(5) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C15 1.494(5) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C5 N2 C1 C2 0.7(6) . . . .
N2 C1 C2 C3 0.5(6) . . . .
C1 C2 C3 C4 -0.9(6) . . . .
C1 C2 C3 S1 -179.4(3) . . . .
C6 S1 C3 C2 -1.3(4) . . . .
C6 S1 C3 C4 -179.8(3) . . . .
C2 C3 C4 C5 0.1(6) . . . .
S1 C3 C4 C5 178.8(3) . . . .
C1 N2 C5 C4 -1.5(6) . . . .
C3 C4 C5 N2 1.1(6) . . . .
C3 S1 C6 C7 180.0(2) . . . .
S1 C6 C7 C11 8.4(5) . . . .
S1 C6 C7 C8 -171.6(3) . . . .
C11 C7 C8 C9 0.6(6) . . . .
C6 C7 C8 C9 -179.4(3) . . . .
C10 N1 C9 C8 0.3(7) . . . .
C7 C8 C9 N1 -0.3(7) . . . .
C9 N1 C10 C11 -0.4(7) . . . .
N1 C10 C11 C7 0.7(7) . . . .
C8 C7 C11 C10 -0.7(6) . . . .
C6 C7 C11 C10 179.3(4) . . . .
O3 C12 C13 C14 0.1(6) . . . .
O4 C12 C13 C14 179.8(3) . . . .
C12 C13 C14 C15 179.6(3) . . . .
C13 C14 C15 O2 -0.1(6) . . . .
C13 C14 C15 O1 179.5(3) . . . .
