#------------------------------------------------------------------------------
#$Date: 2023-11-22 11:57:20 +0200 (Wed, 22 Nov 2023) $
#$Revision: 287730 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/76/8107657.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_8107657
loop_
_publ_author_name
'Fang, Yu'
'Zhang, Cheng'
'Yin, Meng-Qing'
'Yang, Xiao-Die'
'Ma, Wen-Jing'
_publ_section_title
;
 The crystal structure of
 5-chloro-6′-methyl-3-(4-(methylsulfonyl)phenyl)-[2,3′-bipyridin]-1′-ium
 4-methylbenzenesulfonate
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1051
_journal_page_last               1053
_journal_paper_doi               10.1515/ncrs-2023-0285
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C18 H16 Cl N2 O2 S, C7 H7 O3 S'
_chemical_formula_sum            'C25 H23 Cl N2 O5 S2'
_chemical_formula_weight         531.056
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_Int_Tables_number      15
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 112.32(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   36.911(9)
_cell_length_b                   9.931(2)
_cell_length_c                   14.795(3)
_cell_measurement_reflns_used    9199
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.47
_cell_measurement_theta_min      1.19
_cell_volume                     5017(2)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.9944
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.9996
_diffrn_reflns_Laue_measured_fraction_max 0.9944
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9199
_diffrn_reflns_point_group_measured_fraction_full 0.9996
_diffrn_reflns_point_group_measured_fraction_max 0.9944
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         25.47
_diffrn_reflns_theta_min         1.19
_exptl_absorpt_coefficient_mu    0.358
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       needle
_exptl_crystal_F_000             2212.448
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.4303
_refine_diff_density_min         -0.4502
_refine_diff_density_rms         0.0823
_refine_ls_d_res_high            0.8263
_refine_ls_d_res_low             17.0721
_refine_ls_extinction_coef       0.0021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0785
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    40
_refine_ls_number_parameters     320
_refine_ls_number_reflns         4617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0785
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0656P)²+4.0958P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1447
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              41
_reflns_limit_h_min              -44
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                3253
_reflns_number_total             4617
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            suppl_j_ncrs-2023-0285_suppl_001.cif
_cod_data_source_block           ETR-TsOH
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_database_code               8107657
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2
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_refinement_flags_posn
C1 C 0.68970(8) 0.0244(3) 0.6246(2) 0.0440(7) Uani 1.000000 .
C2 C 0.66503(9) -0.0844(3) 0.6133(2) 0.0480(8) Uani 1.000000 .
H2 H 0.67475(9) -0.1716(3) 0.6173(2) 0.0576(9) Uiso 1.000000 R
C3 C 0.62602(9) -0.0639(3) 0.5961(2) 0.0441(7) Uani 1.000000 .
H3 H 0.60966(9) -0.1375(3) 0.5899(2) 0.0529(9) Uiso 1.000000 R
C4 C 0.61087(8) 0.0661(3) 0.58801(19) 0.0367(6) Uani 1.000000 .
C5 C 0.63652(8) 0.1708(3) 0.6003(2) 0.0427(7) Uani 1.000000 .
H5 H 0.62754(8) 0.2589(3) 0.5961(2) 0.0513(8) Uiso 1.000000 R
C6 C 0.73222(9) 0.0148(4) 0.6433(3) 0.0626(10) Uani 1.000000 .
H6a H 0.73541(9) -0.013(2) 0.5845(6) 0.0938(15) Uiso 1.000000 GR
H6b H 0.74431(17) 0.1011(7) 0.6634(18) 0.0938(15) Uiso 1.000000 GR
H6c H 0.74434(17) -0.0500(19) 0.6939(13) 0.0938(15) Uiso 1.000000 GR
C7 C 0.57008(8) 0.0947(3) 0.57652(19) 0.0366(6) Uani 1.000000 .
C8 C 0.52353(9) 0.0537(3) 0.6402(2) 0.0451(7) Uani 1.000000 .
H8 H 0.51452(9) 0.0032(3) 0.6804(2) 0.0541(9) Uiso 1.000000 R
C9 C 0.50082(8) 0.1583(3) 0.5871(2) 0.0429(7) Uani 1.000000 .
C10 C 0.51190(8) 0.2278(3) 0.52118(19) 0.0411(7) Uani 1.000000 .
H10 H 0.49608(8) 0.2955(3) 0.48255(19) 0.0493(8) Uiso 1.000000 R
C11 C 0.54706(8) 0.1949(3) 0.51371(19) 0.0368(6) Uani 1.000000 .
C12 C 0.55882(8) 0.2596(3) 0.43744(19) 0.0381(6) Uani 1.000000 .
C13 C 0.56581(9) 0.1792(3) 0.3691(2) 0.0426(7) Uani 1.000000 .
H13 H 0.56338(9) 0.0863(3) 0.3718(2) 0.0511(8) Uiso 1.000000 R
C14 C 0.57628(9) 0.2349(3) 0.2972(2) 0.0434(7) Uani 1.000000 .
H14 H 0.58034(9) 0.1803(3) 0.2509(2) 0.0520(8) Uiso 1.000000 R
C15 C 0.58068(9) 0.3733(3) 0.2949(2) 0.0421(7) Uani 1.000000 .
C16 C 0.57376(12) 0.4542(3) 0.3616(2) 0.0602(9) Uani 1.000000 .
H16 H 0.57674(12) 0.5470(3) 0.3593(2) 0.0722(11) Uiso 1.000000 R
C17 C 0.56237(11) 0.3986(3) 0.4323(2) 0.0548(9) Uani 1.000000 .
H17 H 0.55708(11) 0.4541(3) 0.4764(2) 0.0658(10) Uiso 1.000000 R
C18 C 0.64601(11) 0.4175(5) 0.2509(3) 0.0770(12) Uani 1.000000 .
H18a H 0.65154(11) 0.3230(5) 0.261(2) 0.1155(18) Uiso 1.000000 GR
H18b H 0.65666(17) 0.451(3) 0.2055(10) 0.1155(18) Uiso 1.000000 GR
H18c H 0.65766(15) 0.464(2) 0.3120(11) 0.1155(18) Uiso 1.000000 GR
C19 C 0.75381(9) 0.5189(3) 0.5957(2) 0.0490(8) Uani 1.000000 .
C20 C 0.78265(10) 0.4261(4) 0.6016(2) 0.0573(9) Uani 1.000000 .
H20 H 0.77680(10) 0.3347(4) 0.5938(2) 0.0688(11) Uiso 1.000000 R
C21 C 0.81984(10) 0.4702(4) 0.6189(3) 0.0609(9) Uani 1.000000 .
H21 H 0.83900(10) 0.4072(4) 0.6226(3) 0.0731(11) Uiso 1.000000 R
C22 C 0.82989(10) 0.6041(4) 0.6309(2) 0.0563(9) Uani 1.000000 .
C23 C 0.80113(11) 0.6940(4) 0.6250(3) 0.0724(11) Uani 1.000000 .
H23 H 0.80716(11) 0.7852(4) 0.6330(3) 0.0868(13) Uiso 1.000000 R
C24 C 0.76322(11) 0.6529(4) 0.6074(3) 0.0689(10) Uani 1.000000 .
H24 H 0.74414(11) 0.7163(4) 0.6036(3) 0.0827(13) Uiso 1.000000 R
C25 C 0.87037(10) 0.6521(5) 0.6459(3) 0.0764(12) Uani 1.000000 .
H25a H 0.88805(19) 0.5769(7) 0.662(2) 0.1146(18) Uiso 1.000000 GR
H25b H 0.8701(2) 0.693(3) 0.5869(8) 0.1146(18) Uiso 1.000000 GR
H25c H 0.8789(4) 0.717(2) 0.6980(15) 0.1146(18) Uiso 1.000000 GR
Cl02 Cl 0.45825(2) 0.19849(10) 0.60421(7) 0.0605(3) Uani 1.000000 .
N1 N 0.67431(7) 0.1475(3) 0.61843(18) 0.0459(6) Uani 1.000000 .
H1 H 0.68960(7) 0.2156(3) 0.62654(18) 0.0550(8) Uiso 1.000000 R
N2 N 0.55773(7) 0.0226(3) 0.63597(17) 0.0431(6) Uani 1.000000 .
O1 O 0.57901(8) 0.3620(3) 0.11824(15) 0.0639(7) Uani 1.000000 .
O2 O 0.58822(9) 0.5838(3) 0.19742(19) 0.0782(8) Uani 1.000000 .
O3 O 0.69416(8) 0.3843(4) 0.48241(18) 0.0933(10) Uani 1.000000 .
O4 O 0.68228(9) 0.5867(3) 0.5588(3) 0.1136(13) Uani 1.000000 .
O5 O 0.70588(8) 0.3882(3) 0.65132(17) 0.0768(8) Uani 1.000000 .
S1 S 0.59589(3) 0.44228(8) 0.20461(6) 0.0510(3) Uani 1.000000 .
S2 S 0.70493(3) 0.46650(10) 0.56784(7) 0.0570(3) Uani 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.86690 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
O2 S1 O1 118.28(16) . .
C15 S1 O1 107.60(14) . .
C15 S1 O2 109.03(15) . .
C18 S1 O1 108.16(19) . .
C18 S1 O2 108.8(2) . .
C18 S1 C15 104.12(16) . .
O3 S2 O5 110.86(18) . .
C19 S2 O5 105.50(15) . .
C19 S2 O3 106.91(16) . .
O4 S2 O5 110.5(2) . .
O4 S2 O3 115.9(2) . .
O4 S2 C19 106.47(17) . .
C8 N2 C7 118.3(3) . .
C5 N1 H1 118.11(18) . .
C1 N1 H1 118.11(16) . .
C1 N1 C5 123.8(3) . .
C10 C11 C7 117.7(2) . .
C12 C11 C7 121.7(2) . .
C12 C11 C10 120.5(3) . .
C3 C4 C7 123.1(3) . .
C5 C4 C7 119.4(3) . .
C5 C4 C3 117.2(3) . .
C11 C7 N2 122.8(2) . .
C4 C7 N2 114.0(2) . .
C4 C7 C11 123.1(2) . .
H10 C10 C11 120.73(16) . .
C9 C10 C11 118.5(3) . .
C9 C10 H10 120.73(17) . .
C13 C12 C11 119.3(3) . .
C17 C12 C11 121.8(3) . .
C17 C12 C13 118.9(3) . .
C14 C15 S1 118.5(2) . .
C16 C15 S1 121.0(2) . .
C16 C15 C14 120.5(3) . .
C10 C9 Cl02 121.2(2) . .
C8 C9 Cl02 118.6(2) . .
C8 C9 C10 120.1(3) . .
C9 C8 N2 122.2(3) . .
H8 C8 N2 118.90(17) . .
H8 C8 C9 118.90(17) . .
H3 C3 C4 119.69(17) . .
C2 C3 C4 120.6(3) . .
C2 C3 H3 119.69(19) . .
H13 C13 C12 119.46(17) . .
C14 C13 C12 121.1(3) . .
C14 C13 H13 119.46(18) . .
C4 C5 N1 120.7(3) . .
H5 C5 N1 119.64(18) . .
H5 C5 C4 119.64(17) . .
C13 C14 C15 119.2(3) . .
H14 C14 C15 120.42(17) . .
H14 C14 C13 120.42(18) . .
C2 C1 N1 117.6(3) . .
C6 C1 N1 117.5(3) . .
C6 C1 C2 124.9(3) . .
C1 C2 C3 120.0(3) . .
H2 C2 C3 119.98(19) . .
H2 C2 C1 119.98(18) . .
C20 C19 S2 120.7(3) . .
C24 C19 S2 120.2(3) . .
C24 C19 C20 119.1(3) . .
H17 C17 C12 119.99(17) . .
C16 C17 C12 120.0(3) . .
C16 C17 H17 119.99(19) . .
C23 C22 C21 117.4(3) . .
C25 C22 C21 122.1(4) . .
C25 C22 C23 120.5(4) . .
H20 C20 C19 120.3(2) . .
C21 C20 C19 119.4(3) . .
C21 C20 H20 120.3(2) . .
C17 C16 C15 120.3(3) . .
H16 C16 C15 119.85(18) . .
H16 C16 C17 119.85(19) . .
C20 C21 C22 122.4(3) . .
H21 C21 C22 118.8(2) . .
H21 C21 C20 118.8(2) . .
H6a C6 C1 109.5 . .
H6b C6 C1 109.5 . .
H6b C6 H6a 109.5 . .
H6c C6 C1 109.5 . .
H6c C6 H6a 109.5 . .
H6c C6 H6b 109.5 . .
H23 C23 C22 119.1(2) . .
C24 C23 C22 121.7(4) . .
C24 C23 H23 119.1(2) . .
C23 C24 C19 120.0(4) . .
H24 C24 C19 120.0(2) . .
H24 C24 C23 120.0(2) . .
H25a C25 C22 109.5 . .
H25b C25 C22 109.5 . .
H25b C25 H25a 109.5 . .
H25c C25 C22 109.5 . .
H25c C25 H25a 109.5 . .
H25c C25 H25b 109.5 . .
H18a C18 S1 109.5 . .
H18b C18 S1 109.5 . .
H18b C18 H18a 109.5 . .
H18c C18 S1 109.5 . .
H18c C18 H18a 109.5 . .
H18c C18 H18b 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.432(2) .
S1 O2 1.429(3) .
S1 C15 1.771(3) .
S1 C18 1.729(4) .
Cl02 C9 1.730(3) .
S2 O5 1.449(3) .
S2 O3 1.429(3) .
S2 C19 1.769(3) .
S2 O4 1.434(3) .
N2 C7 1.341(4) .
N2 C8 1.324(4) .
N1 H1 0.8600 .
N1 C5 1.337(4) .
N1 C1 1.336(4) .
C11 C7 1.405(4) .
C11 C10 1.383(4) .
C11 C12 1.499(4) .
C4 C7 1.477(4) .
C4 C3 1.394(4) .
C4 C5 1.371(4) .
C10 H10 0.9300 .
C10 C9 1.377(4) .
C12 C13 1.387(4) .
C12 C17 1.392(4) .
C15 C14 1.386(4) .
C15 C16 1.370(4) .
C9 C8 1.379(4) .
C8 H8 0.9300 .
C3 H3 0.9300 .
C3 C2 1.379(4) .
C13 H13 0.9300 .
C13 C14 1.377(4) .
C5 H5 0.9300 .
C14 H14 0.9300 .
C1 C2 1.382(4) .
C1 C6 1.490(4) .
C2 H2 0.9300 .
C19 C20 1.385(5) .
C19 C24 1.370(5) .
C17 H17 0.9300 .
C17 C16 1.381(4) .
C22 C21 1.374(5) .
C22 C23 1.364(5) .
C22 C25 1.502(5) .
C20 H20 0.9300 .
C20 C21 1.369(5) .
C16 H16 0.9300 .
C21 H21 0.9300 .
C6 H6a 0.9600 .
C6 H6b 0.9600 .
C6 H6c 0.9600 .
C23 H23 0.9300 .
C23 C24 1.384(5) .
C24 H24 0.9300 .
C25 H25a 0.9600 .
C25 H25b 0.9600 .
C25 H25c 0.9600 .
C18 H18a 0.9600 .
C18 H18b 0.9600 .
C18 H18c 0.9600 .
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
S1 C15 C14 C13 177.7(2) . . . .
S1 C15 C16 C17 -179.2(3) . . . .
Cl02 C9 C10 C11 177.3(2) . . . .
Cl02 C9 C8 N2 -175.5(2) . . . .
S2 C19 C20 C21 177.1(3) . . . .
S2 C19 C24 C23 -177.2(3) . . . .
N2 C7 C11 C10 6.3(3) . . . .
N2 C7 C11 C12 -170.6(3) . . . .
N2 C7 C4 C3 44.2(3) . . . .
N2 C7 C4 C5 -129.6(2) . . . .
N2 C8 C9 C10 5.2(4) . . . .
N1 C5 C4 C7 174.8(2) . . . .
N1 C5 C4 C3 0.6(3) . . . .
N1 C1 C2 C3 0.1(3) . . . .
C11 C7 C4 C3 -139.9(3) . . . .
C11 C7 C4 C5 46.3(3) . . . .
C11 C10 C9 C8 -3.4(3) . . . .
C11 C12 C13 C14 179.3(3) . . . .
C11 C12 C17 C16 179.2(3) . . . .
C4 C3 C2 C1 1.3(3) . . . .
C12 C13 C14 C15 1.4(3) . . . .
C12 C17 C16 C15 1.6(4) . . . .
C3 C2 C1 C6 -179.9(3) . . . .
C19 C20 C21 C22 0.1(4) . . . .
C19 C24 C23 C22 0.2(5) . . . .
