#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/49/4504915.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_4504915
loop_
_publ_author_name
'Bis, Joanna A.'
'Zaworotko, Michael J.'
_publ_section_title
;
 The 2-Aminopyridinium-carboxylate Supramolecular Heterosynthon:  A
 Robust Motif for Generation of Multiple-Component Crystals
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1169
_journal_paper_doi               10.1021/cg049622c
_journal_volume                  5
_journal_year                    2005
_chemical_formula_moiety         '2(C6 H9 N2), C6 H4 O4 S, C6 H2 O4 S'
_chemical_formula_sum            'C24 H24 N4 O8 S2'
_chemical_formula_weight         560.59
_chemical_melting_point          494.5(5)
_chemical_name_common
;
2-amino-5-picolinium 2,5-thiophenedicarboxylate 2,5-thiophenedicarboxylic acid 
;
_chemical_name_systematic
; 
2-amino-5-picolinium 2,5-thiophenedicarboxylate 2,5-thiophenedicarboxylic acid  
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.7349(10)
_cell_length_b                   18.7523(12)
_cell_length_c                   9.0740(6)
_cell_measurement_temperature    100(2)
_cell_volume                     2507.3(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            14070
_diffrn_reflns_theta_full        27.07
_diffrn_reflns_theta_max         27.07
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.780
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhombic
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0475P)²+1.2255P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0907
_reflns_number_gt                2579
_reflns_number_total             2846
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg049622csi20041104_044103.cif
_cod_data_source_block           9
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '494-495 K' was changed to '494.5(5)'
- the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'constra' was replaced with the
value 'constr' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_sg_symbol_Hall     'P 2ac 2n '
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               4504915
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N11 N 0.52984(8) 0.47217(6) 0.17997(12) 0.0151(2) Uani 1 1 d .
H11 H 0.5361 0.5100 0.2365 0.018 Uiso 1 1 calc R
N12 N 0.68579(8) 0.47157(6) 0.15153(14) 0.0209(3) Uani 1 1 d .
H12A H 0.7355 0.4580 0.1061 0.025 Uiso 1 1 d R
H12B H 0.6911 0.5112 0.2044 0.025 Uiso 1 1 d R
C12 C 0.60500(9) 0.44286(7) 0.12092(15) 0.0155(3) Uani 1 1 d .
C13 C 0.59366(10) 0.38306(7) 0.02845(15) 0.0175(3) Uani 1 1 d .
H13 H 0.6449 0.3609 -0.0157 0.021 Uiso 1 1 calc R
C14 C 0.50839(10) 0.35730(7) 0.00291(16) 0.0180(3) Uani 1 1 d .
H14 H 0.5010 0.3175 -0.0608 0.022 Uiso 1 1 calc R
C15 C 0.43077(9) 0.38828(7) 0.06874(15) 0.0162(3) Uani 1 1 d .
C16 C 0.44476(9) 0.44621(7) 0.15668(15) 0.0159(3) Uani 1 1 d .
H16 H 0.3944 0.4688 0.2024 0.019 Uiso 1 1 calc R
C17 C 0.33714(10) 0.36023(8) 0.03901(16) 0.0216(3) Uani 1 1 d .
H17A H 0.3312 0.3126 0.0747 0.026 Uiso 1 1 d R
H17B H 0.3238 0.3610 -0.0624 0.026 Uiso 1 1 d R
H17C H 0.2930 0.3892 0.0904 0.026 Uiso 1 1 d R
S21 S 0.35071(3) 0.7500 0.32664(5) 0.01374(12) Uani 1 2 d S
O21 O 0.33334(7) 0.58874(5) 0.29816(11) 0.0184(2) Uani 1 1 d .
O22 O 0.40174(7) 0.56627(5) 0.51549(11) 0.0200(2) Uani 1 1 d .
H22 H 0.3882 0.5211 0.5004 0.024 Uiso 1 1 d R
C22 C 0.38510(9) 0.68458(7) 0.44721(15) 0.0142(3) Uani 1 1 d .
C23 C 0.42078(9) 0.71240(7) 0.57468(15) 0.0173(3) Uani 1 1 d .
H23 H 0.4429 0.6842 0.6538 0.021 Uiso 1 1 calc R
C24 C 0.37095(9) 0.60844(7) 0.41065(15) 0.0147(3) Uani 1 1 d .
S31 S 0.10475(3) 0.7500 0.16134(5) 0.01245(12) Uani 1 2 d S
C32 C 0.14221(9) 0.68446(7) 0.04446(14) 0.0129(3) Uani 1 1 d .
C33 C 0.18316(9) 0.71233(7) -0.07842(15) 0.0169(3) Uani 1 1 d .
H33 H 0.2087 0.6842 -0.1549 0.020 Uiso 1 1 calc R
C34 C 0.12258(9) 0.60860(7) 0.07936(15) 0.0139(3) Uani 1 1 d .
O31 O 0.08004(7) 0.59605(5) 0.19586(11) 0.0195(2) Uani 1 1 d .
O32 O 0.14960(7) 0.56257(5) -0.01291(12) 0.0196(2) 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
C12 N11 C16 123.32(12) . .
N12 C12 N11 119.05(12) . .
N12 C12 C13 123.35(12) . .
N11 C12 C13 117.61(12) . .
C14 C13 C12 119.41(13) . .
C13 C14 C15 121.78(13) . .
C16 C15 C14 116.87(13) . .
C16 C15 C17 121.56(13) . .
C14 C15 C17 121.54(12) . .
N11 C16 C15 120.99(13) . .
C22 S21 C22 90.99(9) 7_575 .
C23 C22 C24 127.51(12) . .
C23 C22 S21 112.18(10) . .
C24 C22 S21 120.25(10) . .
C22 C23 C23 112.32(8) . 7_575
O21 C24 O22 125.39(12) . .
O21 C24 C22 122.96(12) . .
O22 C24 C22 111.62(11) . .
C32 S31 C32 91.57(9) . 7_575
C33 C32 C34 128.60(12) . .
C33 C32 S31 111.80(10) . .
C34 C32 S31 119.46(10) . .
C32 C33 C33 112.40(7) . 7_575
O31 C34 O32 126.00(12) . .
O31 C34 C32 117.23(12) . .
O32 C34 C32 116.77(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C12 1.3476(17) .
N11 C16 1.3613(17) .
N12 C12 1.3357(18) .
C12 C13 1.4106(19) .
C13 C14 1.366(2) .
C14 C15 1.415(2) .
C15 C16 1.3636(19) .
C15 C17 1.5010(19) .
S21 C22 1.7200(13) 7_575
S21 C22 1.7200(13) .
O21 C24 1.2188(17) .
O22 C24 1.3177(16) .
C22 C23 1.3735(19) .
C22 C24 1.4806(18) .
C23 C23 1.410(3) 7_575
S31 C32 1.7146(13) .
S31 C32 1.7146(13) 7_575
C32 C33 1.3713(18) .
C32 C34 1.4859(18) .
C33 C33 1.413(3) 7_575
C34 O31 1.2513(17) .
C34 O32 1.2666(16) .
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_site_symmetry_A
O22 H22 O32 0.88 1.67 2.5448(14) 172.1 2_565
N12 H12B O21 0.89 2.55 3.1246(15) 123.0 6_656
N12 H12B O31 0.89 2.46 3.1298(15) 133.0 6_656
N12 H12A O32 0.88 1.93 2.8062(15) 174.0 5_665
N11 H11 O31 0.88 1.84 2.6858(15) 159.4 6_656
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_4
C16 N11 C12 N12 -179.18(12) . .
C16 N11 C12 C13 1.2(2) . .
N12 C12 C13 C14 -179.86(13) . .
N11 C12 C13 C14 -0.2(2) . .
C12 C13 C14 C15 -1.1(2) . .
C13 C14 C15 C16 1.4(2) . .
C13 C14 C15 C17 179.35(13) . .
C12 N11 C16 C15 -0.8(2) . .
C14 C15 C16 N11 -0.5(2) . .
C17 C15 C16 N11 -178.42(12) . .
C22 S21 C22 C23 0.41(13) 7_575 .
C22 S21 C22 C24 177.77(7) 7_575 .
C24 C22 C23 C23 -177.43(11) . 7_575
S21 C22 C23 C23 -0.31(10) . 7_575
C23 C22 C24 O21 175.15(13) . .
S21 C22 C24 O21 -1.76(19) . .
C23 C22 C24 O22 -3.3(2) . .
S21 C22 C24 O22 179.81(9) . .
C32 S31 C32 C33 0.92(13) 7_575 .
C32 S31 C32 C34 -175.11(7) 7_575 .
C34 C32 C33 C33 174.88(11) . 7_575
S31 C32 C33 C33 -0.70(10) . 7_575
C33 C32 C34 O31 -176.38(13) . .
S31 C32 C34 O31 -1.10(17) . .
C33 C32 C34 O32 2.8(2) . .
S31 C32 C34 O32 178.05(10) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145662
