#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/92/2209209.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_2209209
loop_
_publ_author_name
'Wang, Zi-Liang'
'Li, Ming-Xue'
'Wei, Lin-Heng'
'Wang, Jing-Ping'
_publ_section_title
;
 2,6-Dimethylpyridinium saccharinate
;
_journal_coeditor_code           HK2031
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2127
_journal_page_last               o2128
_journal_paper_doi               10.1107/S1600536806015297
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C7 H10 N + , C7 H4 N O3 S -'
_chemical_formula_moiety         'C7 H10 N + , C7 H4 N O3 S -'
_chemical_formula_sum            'C14 H14 N2 O3 S'
_chemical_formula_weight         290.33
_chemical_name_systematic
;
2,6-Dimethylpyridinium saccharinate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.674(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5366(18)
_cell_length_b                   8.2522(11)
_cell_length_c                   14.710(2)
_cell_measurement_reflns_used    2471
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.83
_cell_volume                     1393.7(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  PLATON
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'thin-slice ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5910
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.233
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0826P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1402
_reflns_number_gt                2093
_reflns_number_total             2726
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2031.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209209
_cod_database_fobs_code          2209209
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_refinement_flags
_atom_site_occupancy
S S1 0.79823(4) 0.29302(6) 0.16341(4) 0.0561(2) Uani d . 1
O O1 0.82928(17) 0.21998(19) 0.08862(14) 0.0823(5) Uani d . 1
O O2 0.87297(14) 0.25233(18) 0.26341(13) 0.0740(5) Uani d . 1
O O3 0.50148(12) 0.4078(2) 0.11922(13) 0.0800(5) Uani d . 1
N N1 0.66473(16) 0.2577(2) 0.14401(15) 0.0625(5) Uani d . 1
N N2 0.31132(14) 0.2555(2) 0.11152(11) 0.0479(4) Uani d D 1
C C1 0.78682(15) 0.5064(2) 0.14980(13) 0.0461(4) Uani d . 1
C C2 0.86928(18) 0.6217(3) 0.15757(14) 0.0569(5) Uani d . 1
H H2 0.9454 0.5937 0.1689 0.068 Uiso calc R 1
C C3 0.8328(2) 0.7824(3) 0.14758(16) 0.0658(6) Uani d . 1
H H3 0.8856 0.8642 0.1519 0.079 Uiso calc R 1
C C4 0.7210(2) 0.8221(3) 0.13156(16) 0.0671(6) Uani d . 1
H H4 0.6993 0.9306 0.1258 0.080 Uiso calc R 1
C C5 0.6396(2) 0.7047(2) 0.12369(16) 0.0601(6) Uani d . 1
H H5 0.5634 0.7326 0.1121 0.072 Uiso calc R 1
C C6 0.67428(15) 0.5442(2) 0.13346(12) 0.0461(4) Uani d . 1
C C7 0.60497(17) 0.3956(2) 0.13099(15) 0.0552(5) Uani d . 1
C C8 0.22973(19) 0.3617(3) 0.10856(14) 0.0574(5) Uani d . 1
C C9 0.1236(2) 0.2999(4) 0.10037(18) 0.0763(7) Uani d . 1
H H9 0.0639 0.3694 0.0976 0.092 Uiso calc R 1
C C10 0.1073(2) 0.1357(4) 0.09644(19) 0.0846(8) Uani d . 1
H H10 0.0363 0.0940 0.0917 0.102 Uiso calc R 1
C C11 0.1927(2) 0.0329(3) 0.09936(17) 0.0759(7) Uani d . 1
H H11 0.1803 -0.0784 0.0961 0.091 Uiso calc R 1
C C12 0.29770(19) 0.0937(3) 0.10710(14) 0.0573(5) Uani d . 1
C C13 0.2598(2) 0.5362(3) 0.1168(2) 0.0832(8) Uani d . 1
H H13A 0.3102 0.5612 0.1842 0.125 Uiso calc R 1
H H13B 0.1899 0.5996 0.0975 0.125 Uiso calc R 1
H H13C 0.2987 0.5611 0.0740 0.125 Uiso calc R 1
C C14 0.3975(2) -0.0086(3) 0.1122(2) 0.0815(7) Uani d . 1
H H14A 0.4593 0.0596 0.1116 0.122 Uiso calc R 1
H H14B 0.3730 -0.0801 0.0561 0.122 Uiso calc R 1
H H14C 0.4247 -0.0712 0.1723 0.122 Uiso calc R 1
H H1 0.3761(12) 0.291(3) 0.1160(17) 0.066(7) Uiso d D 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
O2 S1 O1 114.91(11)
O2 S1 N1 110.20(10)
O1 S1 N1 111.74(11)
O2 S1 C1 109.83(9)
O1 S1 C1 111.37(9)
N1 S1 C1 97.42(9)
C7 N1 S1 110.84(14)
C8 N2 C12 124.77(19)
C8 N2 H1 118.6(16)
C12 N2 H1 116.6(16)
C6 C1 C2 122.97(19)
C6 C1 S1 106.09(14)
C2 C1 S1 130.87(16)
C1 C2 C3 116.5(2)
C1 C2 H2 121.7
C3 C2 H2 121.7
C4 C3 C2 121.2(2)
C4 C3 H3 119.4
C2 C3 H3 119.4
C3 C4 C5 121.4(2)
C3 C4 H4 119.3
C5 C4 H4 119.3
C4 C5 C6 118.3(2)
C4 C5 H5 120.9
C6 C5 H5 120.9
C1 C6 C5 119.69(18)
C1 C6 C7 111.43(16)
C5 C6 C7 128.87(19)
O3 C7 N1 125.8(2)
O3 C7 C6 120.09(19)
N1 C7 C6 114.14(17)
N2 C8 C9 117.3(2)
N2 C8 C13 118.0(2)
C9 C8 C13 124.7(2)
C10 C9 C8 119.4(2)
C10 C9 H9 120.3
C8 C9 H9 120.3
C11 C10 C9 121.1(2)
C11 C10 H10 119.5
C9 C10 H10 119.5
C10 C11 C12 119.7(2)
C10 C11 H11 120.2
C12 C11 H11 120.2
N2 C12 C11 117.8(2)
N2 C12 C14 118.3(2)
C11 C12 C14 123.9(2)
C8 C13 H13A 109.5
C8 C13 H13B 109.5
H13A C13 H13B 109.5
C8 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C12 C14 H14A 109.5
C12 C14 H14B 109.5
H14A C14 H14B 109.5
C12 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4309(17)
S1 O1 1.4385(17)
S1 N1 1.6073(19)
S1 C1 1.771(2)
O3 C7 1.242(3)
N1 C7 1.333(3)
N2 C8 1.335(3)
N2 C12 1.344(3)
N2 H1 0.840(10)
C1 C6 1.369(3)
C1 C2 1.376(3)
C2 C3 1.391(3)
C2 H2 0.9300
C3 C4 1.365(3)
C3 H3 0.9300
C4 C5 1.378(3)
C4 H4 0.9300
C5 C6 1.383(3)
C5 H5 0.9300
C6 C7 1.495(3)
C8 C9 1.385(3)
C8 C13 1.481(3)
C9 C10 1.368(4)
C9 H9 0.9300
C10 C11 1.354(4)
C10 H10 0.9300
C11 C12 1.370(3)
C11 H11 0.9300
C12 C14 1.486(3)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H1 O3 0.840(10) 1.829(11) 2.657(2) 168(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21128162
2 PubChem 139069660
