#------------------------------------------------------------------------------
#$Date: 2022-09-28 18:08:17 +0300 (Wed, 28 Sep 2022) $
#$Revision: 278247 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/99/2009913.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_2009913
loop_
_publ_author_name
'Sillanpää, R.'
'Kivekäs, R.'
'Escriche, L.'
'Sánchez-Castelló, G.'
'Teixidor, F.'
_publ_section_title
;
 2,6-Bis(p-nitrophenylthiomethyl)pyridine
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1284
_journal_page_last               1286
_journal_paper_doi               10.1107/S0108270193013617
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C19 H15 N3 O4 S2'
_chemical_formula_sum            'C19 H15 N3 O4 S2'
_chemical_formula_weight         413.47
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                98.50(2)
_cell_angle_beta                 103.95(2)
_cell_angle_gamma                74.240(10)
_cell_formula_units_Z            2
_cell_length_a                   10.779(2)
_cell_length_b                   12.241(2)
_cell_length_c                   7.540(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      20
_cell_measurement_theta_min      16
_cell_volume                     925.6(3)
_diffrn_measurement_device       'Rigaku AFC5S'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3443
_diffrn_reflns_theta_max         25
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       needle
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.29
_refine_ls_goodness_of_fit_obs   1.25
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     298
_refine_ls_number_reflns         1963
_refine_ls_R_factor_obs          0.051
_refine_ls_shift/esd_max         0.03
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/σ²(F)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.046
_reflns_number_observed          1963
_reflns_number_total             3254
_reflns_observed_criterion       I>\s(I)
_cod_data_source_file            ab1100.cif
_cod_data_source_block           ab1100_structure_1_of_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/\s^2^(F)' was changed to
'calc'. New tag '_refine_ls_weighting_details' was created. The value
of the new tag was set to 'w = 1/\s^2^(F)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        925.6(7)
_cod_database_code               2009913
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
S(1) .43960(10) .42936(9) .6825(2)
S(2) .81190(10) .02513(9) .9996(2)
O(1) -.0517(3) .8816(3) .4391(6)
O(2) -.1363(3) .7469(3) .2914(5)
O(3) .2253(3) .2726(3) 1.2039(5)
O(4) .3084(4) .1573(4) 1.4140(6)
N(1) .6938(3) .3101(3) .8209(4)
N(2) -.0470(3) .7810(4) .3957(6)
N(3) .3146(4) .1988(4) 1.2794(7)
C(1) .6904(4) .4204(3) .8705(5)
C(2) .7972(4) .4568(4) .9788(6)
C(3) .9118(4) .3770(4) 1.0386(6)
C(4) .9165(4) .2625(4) .9885(6)
C(5) .8065(4) .2326(3) .8800(5)
C(6) .5635(4) .5047(3) .7990(6)
C(7) .3012(3) .5409(3) .6098(5)
C(8) .1924(4) .5060(4) .5007(6)
C(9) .0795(4) .5840(4) .4312(6)
C(10) .0725(4) .6980(3) .4733(5)
C(11) .1774(4) .7345(3) .5831(6)
C(12) .2918(4) .6561(3) .6504(6)
C(13) .8038(4) .1100(4) .8184(7)
C(14) .6616(4) .0815(3) 1.0709(6)
C(15) .6553(4) .0481(4) 1.2361(7)
C(16) .5433(5) .0860(4) 1.3059(7)
C(17) .4350(4) .1575(3) 1.2068(7)
C(18) .4365(4) .1907(3) 1.0414(7)
C(19) .5499(4) .1530(3) .9718(6)
H(2) .792(4) .540(3) 1.003(5)
H(3) .995(4) .400(3) 1.122(5)
H(4) .990(4) .211(3) 1.032(5)
H(6A) .573(3) .554(3) .715(5)
H(6B) .532(3) .551(3) .895(5)
H(8) .199(4) .428(3) .479(5)
H(9) .012(4) .567(3) .361(5)
H(11) .174(4) .812(3) .618(5)
H(12) .364(4) .681(3) .721(5)
H(13A) .877(4) .073(3) .763(5)
H(13B) .730(4) .102(3) .721(5)
H(15) .732(4) .002(3) 1.300(5)
H(16) .536(4) .063(4) 1.411(6)
H(18) .367(4) .236(3) .973(5)
H(19) .552(4) .176(3) .861(5)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(6) S(1) C(7) 102.7(2) yes
C(13) S(2) C(14) 104.9(2) yes
C(1) N(1) C(5) 117.9(3) yes
O(1) N(2) O(2) 123.1(4) yes
O(1) N(2) C(10) 117.9(4) yes
O(2) N(2) C(10) 119.0(4) yes
O(3) N(3) O(4) 122.9(5) yes
O(3) N(3) C(17) 118.9(5) yes
O(4) N(3) C(17) 118.2(4) yes
N(1) C(1) C(2) 122.7(3) yes
N(1) C(1) C(6) 116.4(3) yes
C(2) C(1) C(6) 120.9(4) yes
C(1) C(2) C(3) 118.9(4) yes
C(2) C(3) C(4) 119.0(4) yes
C(3) C(4) C(5) 118.9(3) yes
N(1) C(5) C(4) 122.6(4) yes
N(1) C(5) C(13) 115.2(3) yes
C(4) C(5) C(13) 122.1(3) yes
S(1) C(6) C(1) 109.6(3) yes
S(1) C(7) C(8) 114.9(3) yes
S(1) C(7) C(12) 126.6(3) yes
C(8) C(7) C(12) 118.5(3) yes
C(7) C(8) C(9) 121.0(4) yes
C(8) C(9) C(10) 119.5(4) yes
N(2) C(10) C(9) 119.3(4) yes
N(2) C(10) C(11) 120.0(4) yes
C(9) C(10) C(11) 120.7(3) yes
C(10) C(11) C(12) 119.9(4) yes
C(7) C(12) C(11) 120.5(4) yes
S(2) C(13) C(5) 114.8(3) yes
S(2) C(14) C(15) 115.9(3) yes
S(2) C(14) C(19) 125.0(4) yes
C(15) C(14) C(19) 119.1(4) yes
C(14) C(15) C(16) 121.4(4) yes
C(15) C(16) C(17) 118.5(5) yes
N(3) C(17) C(16) 119.2(5) yes
N(3) C(17) C(18) 118.9(4) yes
C(16) C(17) C(18) 121.9(4) yes
C(17) C(18) C(19) 119.6(4) yes
C(14) C(19) C(18) 119.6(5) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S(1) C(6) 1.809(5) yes
S(1) C(7) 1.764(3) yes
S(2) C(13) 1.808(6) yes
S(2) C(14) 1.759(4) yes
O(1) N(2) 1.218(6) yes
O(2) N(2) 1.215(5) yes
O(3) N(3) 1.217(5) yes
O(4) N(3) 1.223(8) yes
N(1) C(1) 1.340(5) yes
N(1) C(5) 1.346(4) yes
N(2) C(10) 1.462(5) yes
N(3) C(17) 1.464(7) yes
C(1) C(2) 1.381(6) yes
C(1) C(6) 1.507(5) yes
C(2) C(3) 1.375(5) yes
C(3) C(4) 1.386(6) yes
C(4) C(5) 1.374(6) yes
C(5) C(13) 1.510(6) yes
C(7) C(8) 1.392(6) yes
C(7) C(12) 1.379(6) yes
C(8) C(9) 1.370(5) yes
C(9) C(10) 1.370(6) yes
C(10) C(11) 1.370(6) yes
C(11) C(12) 1.378(5) yes
C(14) C(15) 1.389(7) yes
C(14) C(19) 1.401(5) yes
C(15) C(16) 1.371(7) yes
C(16) C(17) 1.380(6) yes
C(17) C(18) 1.373(8) yes
C(18) C(19) 1.384(7) yes
S(1) H(6)A 3.00(4) no
S(1) H(6)B 3.11(4) no
S(2) H(4) 3.11(4) no
S(2) H(11) 3.25(4) no
S(2) H(13)A 3.39(4) no
S(2) N(3) 3.569(4) no
O(1) H(15) 2.47(4) no
O(1) H(13)A 2.90(4) no
O(1) H(13)A 3.21(4) no
O(1) O(1) 3.310(8) no
O(1) O(4) 3.386(6) no
O(1) C(15) 3.401(5) no
O(2) H(18) 2.77(4) no
O(2) H(15) 3.06(4) no
O(2) O(4) 3.128(5) no
O(2) H(2) 3.22(4) no
O(2) H(8) 3.24(4) no
O(2) H(4) 3.37(4) no
O(2) C(4) 3.504(6) no
O(2) C(18) 3.558(5) no
O(3) H(3) 2.53(4) no
O(3) H(8) 2.61(4) no
O(3) H(4) 2.79(4) no
O(3) H(2) 2.90(4) no
O(3) C(3) 3.271(5) no
O(3) H(6)A 3.32(4) no
C(6) H(6)B 2.97(4) no
C(6) H(18) 3.56(4) no
C(7) H(6)A 3.01(4) no
C(8) H(9) 3.03(4) no
C(8) H(6)A 3.19(4) no
C(8) H(3) 3.44(4) no
O(3) C(8) 3.353(5) no
O(3) C(4) 3.360(5) no
O(4) H(16) 3.06(4) no
O(4) H(8) 3.21(4) no
O(4) H(15) 3.29(4) no
O(4) H(13)B 3.29(4) no
O(4) N(2) 3.323(5) no
N(1) H(6)B 3.55(4) no
N(1) C(11) 3.555(6) no
N(2) H(15) 3.13(4) no
N(2) H(13)A 3.39(4) no
N(2) C(4) 3.429(6) no
N(2) H(4) 3.44(4) no
N(3) H(8) 3.07(4) no
N(3) H(4) 3.51(4) no
N(3) H(6)A 3.54(4) no
C(1) H(6)B 3.23(4) no
C(2) H(3) 3.46(4) no
C(2) C(7) 3.506(6) no
C(2) C(9) 3.569(6) no
C(2) H(9) 3.58(4) no
C(2) H(9) 3.59(4) no
C(3) H(9) 3.30(4) no
C(3) H(9) 3.51(4) no
C(3) H(3) 3.60(4) no
C(5) C(10) 3.530(6) no
C(17) H(12) 3.21(4) no
C(17) H(6)A 3.47(4) no
C(18) H(12) 3.07(4) no
C(18) H(6)B 3.23(4) no
C(18) H(6)A 3.37(4) no
C(18) H(2) 3.54(4) no
C(8) C(9) 3.566(6) no
C(9) H(9) 3.07(4) no
C(9) H(3) 3.14(4) no
C(9) H(8) 3.28(4) no
C(9) C(9) 3.410(10) no
C(11) H(15) 3.54(4) no
C(11) C(15) 3.542(6) no
C(14) H(11) 2.94(4) no
C(14) H(12) 3.07(4) no
C(14) C(17) 3.580(5) no
C(15) H(11) 2.77(4) no
C(15) H(12) 3.24(4) no
C(15) H(13)B 3.55(4) no
C(15) C(18) 3.559(6) no
C(16) H(13)B 3.30(4) no
C(16) H(12) 3.32(4) no
C(16) H(16) 3.39(4) no
C(16) H(11) 3.48(4) no
C(16) C(19) 3.568(6) no
C(16) H(19) 3.59(4) no
H(12) H(18) 3.53(5) no
C(19) H(12) 2.99(4) no
C(19) H(6)B 3.54(4) no
H(2) H(18) 2.82(5) no
H(2) H(3) 2.98(5) no
H(2) H(9) 3.17(5) no
H(3) H(9) 2.53(5) no
H(3) H(8) 3.08(5) no
H(3) H(3) 3.30(7) no
H(6)A H8 3.21(5) no
H(6)A H(18) 3.30(5) no
H(6)A H(6)A 3.49(7) no
H(6)B H(6)B 2.48(7) no
H(6)B H(18) 3.04(5) no
H(8)B H(19) 3.57(5) no
H(8) H(9) 2.80(5) no
H(9) H(9) 2.95(8) no
H(11) H(15) 2.65(5) no
H(11) H(13)A 3.25(5) no
H(11) H(13)B 3.37(5) no
H(12) H(19) 3.42(5) no
H(13)A H(15) 3.55(5) no
H(13)B H(15) 3.23(5) no
H(15) H(18) 3.57(5) no
H(16) H(16) 2.56(8) no
H(16) H(19) 3.45(6) no
H(16) H(19) 3.53(6) no
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_publ_flag
S(1) C(6) C(1) N(1) 6.8(5) yes
S(1) C(6) C(1) C(2) -174.3(3) yes
S(2) C(13) C(5) N(1) -112.0(4) yes
S(2) C(13) C(5) C(4) 68.1(5) yes
O(1) N(2) C(10) C(9) 178.2(4) yes
O(1) N(2) C(10) C(11) -3.4(6) yes
O(2) N(2) C(10) C(9) -2.0(6) yes
O(2) N(2) C(10) C(11) 176.4(4) yes
O(3) N(3) C(17) C(16) 170.9(4) yes
O(3) N(3) C(17) C(18) -9.3(6) yes
O(4) N(3) C(17) C(16) -9.0(7) yes
O(4) N(3) C(17) C(18) 170.7(5) yes
C(1) C(6) S(1) C(7) -179.9(3) yes
C(5) C(13) S(2) C(14) 67.7(4) yes
C(6) S(1) C(7) C(8) 174.8(3) yes
C(6) S(1) C(7) C(12) -5.2(4) yes
C(13) S(2) C(14) C(15) -166.0(3) yes
C(13) S(2) C(14) C(19) 16.0(4) yes
