#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301863 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/35/7203547.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_7203547
loop_
_publ_author_name
'Banerjee, Rahul'
'Saha, Binoy K.'
'Desiraju, Gautam R.'
_publ_section_title
;
 Synthon robustness in saccharinate salts of some substituted pyridines
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              680
_journal_paper_doi               10.1039/b608926g
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C7 H4 N O3 S, C6 H7 N2 O'
_chemical_formula_sum            'C13 H11 N3 O4 S'
_chemical_formula_weight         305.31
_chemical_melting_point          185
_chemical_name_common            'saccharine, isonicotinamide'
_chemical_name_systematic
;
saccharine, isonicotinamide
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.421(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9157(12)
_cell_length_b                   17.351(3)
_cell_length_c                   10.6553(18)
_cell_measurement_reflns_used    2051
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.95
_cell_measurement_theta_min      2.35
_cell_volume                     1248.6(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7458
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Bruker Nonius area detector scaling and absorption correction - V2.10'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0459P)²+0.9620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1010
_reflns_number_gt                2041
_reflns_number_total             2447
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b608926g.txt
_cod_data_source_block           an25_m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P2(1)/c '
_cod_database_code               7203547
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_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.34750(8) 0.25490(3) 0.26723(5) 0.01579(16) Uani 1 1 d . . .
O1 O 0.2544(2) 0.07427(8) 0.41809(14) 0.0186(3) Uani 1 1 d . . .
N3 N 0.8817(3) 0.05902(10) 0.28047(17) 0.0167(4) Uani 1 1 d . . .
O4 O 0.1957(2) -0.03069(9) 0.13408(15) 0.0237(4) Uani 1 1 d . . .
N1 N 0.2180(3) 0.18182(10) 0.29267(16) 0.0160(4) Uani 1 1 d . . .
O2 O 0.2728(2) 0.32529(9) 0.31156(15) 0.0239(4) Uani 1 1 d . . .
N2 N 0.1941(3) 0.07094(11) 0.00209(18) 0.0197(4) Uani 1 1 d . . .
C1 C 0.3233(3) 0.13501(12) 0.38207(19) 0.0156(4) Uani 1 1 d . . .
O3 O 0.3695(2) 0.25682(9) 0.13644(14) 0.0224(4) Uani 1 1 d . . .
C2 C 0.5331(3) 0.16080(12) 0.43186(19) 0.0149(4) Uani 1 1 d . . .
C9 C 0.6060(3) 0.09982(12) 0.1244(2) 0.0179(5) Uani 1 1 d . . .
H9 H 0.5480 0.1349 0.0585 0.021 Uiso 1 1 calc R . .
C7 C 0.5697(3) 0.22860(12) 0.37270(19) 0.0158(4) Uani 1 1 d . . .
C11 C 0.5846(3) -0.01087(12) 0.2542(2) 0.0174(5) Uani 1 1 d . . .
H11 H 0.5120 -0.0528 0.2783 0.021 Uiso 1 1 calc R . .
C13 C 0.2802(3) 0.02433(12) 0.0962(2) 0.0175(5) Uani 1 1 d . . .
C8 C 0.8007(3) 0.10840(12) 0.1875(2) 0.0180(5) Uani 1 1 d . . .
H8 H 0.8776 0.1494 0.1649 0.022 Uiso 1 1 calc R . .
C6 C 0.7508(3) 0.26551(13) 0.3990(2) 0.0196(5) Uani 1 1 d . . .
H6 H 0.7728 0.3116 0.3561 0.024 Uiso 1 1 calc R . .
C10 C 0.4950(3) 0.03932(12) 0.1581(2) 0.0155(4) Uani 1 1 d . . .
C4 C 0.8637(3) 0.16483(13) 0.5535(2) 0.0206(5) Uani 1 1 d . . .
H4 H 0.9664 0.1439 0.6183 0.025 Uiso 1 1 calc R . .
C5 C 0.8989(3) 0.23189(13) 0.4913(2) 0.0211(5) Uani 1 1 d . . .
H5 H 1.0262 0.2551 0.5122 0.025 Uiso 1 1 calc R . .
C12 C 0.7792(3) 0.00036(12) 0.3145(2) 0.0183(5) Uani 1 1 d . . .
H12 H 0.8409 -0.0338 0.3808 0.022 Uiso 1 1 calc R . .
C3 C 0.6820(3) 0.12742(13) 0.5236(2) 0.0179(5) Uani 1 1 d . . .
H3 H 0.6606 0.0805 0.5647 0.021 Uiso 1 1 calc R . .
H2 H 0.257(4) 0.1108(15) -0.028(2) 0.025(7) Uiso 1 1 d . . .
H7 H 0.071(4) 0.0599(15) -0.034(2) 0.030(7) Uiso 1 1 d . . .
H1 H 1.020(5) 0.0656(17) 0.326(3) 0.050(9) Uiso 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
_geom_angle_publ_flag
O3 S1 O2 114.72(10) . . ?
O3 S1 N1 111.17(9) . . ?
O2 S1 N1 111.11(10) . . ?
O3 S1 C7 111.50(10) . . ?
O2 S1 C7 109.60(9) . . ?
N1 S1 C7 97.44(10) . . ?
C12 N3 C8 121.81(19) . . ?
C12 N3 H1 118.3(18) . . ?
C8 N3 H1 119.8(18) . . ?
C1 N1 S1 111.11(14) . . ?
C13 N2 H2 124.2(15) . . ?
C13 N2 H7 115.8(17) . . ?
H2 N2 H7 120(2) . . ?
O1 C1 N1 122.94(19) . . ?
O1 C1 C2 123.07(19) . . ?
N1 C1 C2 113.97(18) . . ?
C7 C2 C3 119.75(19) . . ?
C7 C2 C1 110.47(18) . . ?
C3 C2 C1 129.8(2) . . ?
C8 C9 C10 119.4(2) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C6 C7 C2 123.3(2) . . ?
C6 C7 S1 129.76(18) . . ?
C2 C7 S1 106.96(15) . . ?
C12 C11 C10 119.6(2) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
O4 C13 N2 123.6(2) . . ?
O4 C13 C10 118.76(19) . . ?
N2 C13 C10 117.64(19) . . ?
N3 C8 C9 120.1(2) . . ?
N3 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C7 C6 C5 116.6(2) . . ?
C7 C6 H6 121.7 . . ?
C5 C6 H6 121.7 . . ?
C11 C10 C9 118.72(19) . . ?
C11 C10 C13 117.09(19) . . ?
C9 C10 C13 124.19(19) . . ?
C5 C4 C3 121.7(2) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
N3 C12 C11 120.3(2) . . ?
N3 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C2 C3 C4 117.7(2) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4344(16) . ?
S1 O2 1.4445(16) . ?
S1 N1 1.6086(18) . ?
S1 C7 1.758(2) . ?
O1 C1 1.251(2) . ?
N3 C12 1.335(3) . ?
N3 C8 1.338(3) . ?
N3 H1 0.98(3) . ?
O4 C13 1.232(3) . ?
N1 C1 1.341(3) . ?
N2 C13 1.326(3) . ?
N2 H2 0.91(3) . ?
N2 H7 0.88(3) . ?
C1 C2 1.502(3) . ?
C2 C7 1.384(3) . ?
C2 C3 1.385(3) . ?
C9 C8 1.377(3) . ?
C9 C10 1.392(3) . ?
C9 H9 0.9500 . ?
C7 C6 1.381(3) . ?
C11 C12 1.375(3) . ?
C11 C10 1.385(3) . ?
C11 H11 0.9500 . ?
C13 C10 1.512(3) . ?
C8 H8 0.9500 . ?
C6 C5 1.387(3) . ?
C6 H6 0.9500 . ?
C4 C5 1.386(3) . ?
C4 C3 1.389(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C12 H12 0.9500 . ?
C3 H3 0.9500 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21149311
2 PubChem 139195170
