#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/53/4025319.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_4025319
loop_
_publ_author_name
'Alejandro Dorazco-González'
'Herbert Höpfl'
'Felipe Medrano'
'Anatoly K. Yatsimirsky'
_publ_section_title
;
 Recognition of Anions and Neutral Guests by Dicationic
 Pyridine-2,6-dicarboxamide Receptors
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2259
_journal_page_last               2273
_journal_paper_doi               10.1021/jo100037m
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C17 H15 N5 O2, 2(C H3 O3 S), C2 H3 N'
_chemical_formula_sum            'C21 H24 N6 O8 S2'
_chemical_formula_weight         552.58
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.0980(10)
_cell_angle_beta                 93.6880(10)
_cell_angle_gamma                98.3110(10)
_cell_formula_units_Z            2
_cell_length_a                   6.7521(5)
_cell_length_b                   12.0682(9)
_cell_length_c                   15.8151(12)
_cell_measurement_reflns_used    9584
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.62
_cell_volume                     1196.37(16)
_computing_cell_refinement       'Bruker SAINT'
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11580
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.898
_exptl_absorpt_correction_T_min  0.817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         4195
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0343
_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)+(0.0349P)²+0.9147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0848
_reflns_number_gt                4061
_reflns_number_total             4195
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100037m_si_001.cif
_cod_data_source_block           t9tushm
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025319
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
N1 N 0.7383(2) 0.57946(13) 0.76199(10) 0.0153(3) Uani 1 1 d . . .
N2 N 0.7909(2) 0.46404(13) 0.87758(10) 0.0157(3) Uani 1 1 d D . .
H2' H 0.826(3) 0.4423(18) 0.8240(6) 0.024 Uiso 1 1 d D . .
N3 N 0.7628(2) 0.40572(13) 1.00580(10) 0.0155(3) Uani 1 1 d D . .
H3' H 0.738(3) 0.4751(8) 1.0347(12) 0.023 Uiso 1 1 d D . .
N4 N 0.7818(2) 0.45501(13) 0.59557(10) 0.0161(3) Uani 1 1 d D . .
H4' H 0.822(3) 0.4449(19) 0.6448(8) 0.024 Uiso 1 1 d D . .
N5 N 0.8483(2) 0.26676(13) 0.52639(10) 0.0171(3) Uani 1 1 d D . .
H5' H 0.850(3) 0.2599(19) 0.5789(6) 0.026 Uiso 1 1 d D . .
O1 O 0.69479(19) 0.61282(11) 0.98996(8) 0.0199(3) Uani 1 1 d . . .
O2 O 0.69973(19) 0.60253(11) 0.54448(8) 0.0205(3) Uani 1 1 d . . .
C1 C 0.7200(3) 0.63579(16) 0.70257(12) 0.0162(4) Uani 1 1 d . . .
C2 C 0.6893(3) 0.75262(16) 0.72624(12) 0.0191(4) Uani 1 1 d . . .
H2 H 0.6777 0.7896 0.6820 0.023 Uiso 1 1 calc R . .
C3 C 0.6760(3) 0.81435(16) 0.81601(13) 0.0205(4) Uani 1 1 d . . .
H3 H 0.6566 0.8949 0.8344 0.025 Uiso 1 1 calc R . .
C4 C 0.6912(3) 0.75704(16) 0.87855(12) 0.0193(4) Uani 1 1 d . . .
H4 H 0.6811 0.7967 0.9404 0.023 Uiso 1 1 calc R . .
C5 C 0.7219(3) 0.63942(16) 0.84785(12) 0.0160(4) Uani 1 1 d . . .
C6 C 0.7335(3) 0.57262(16) 0.91257(12) 0.0159(4) Uani 1 1 d . . .
C7 C 0.7983(3) 0.38076(16) 0.91931(12) 0.0150(4) Uani 1 1 d . . .
C8 C 0.8421(3) 0.26892(16) 0.87246(12) 0.0177(4) Uani 1 1 d . . .
H8 H 0.8701 0.2501 0.8117 0.021 Uiso 1 1 calc R . .
C9 C 0.8443(3) 0.18656(16) 0.91493(12) 0.0200(4) Uani 1 1 d . . .
H9 H 0.8735 0.1102 0.8833 0.024 Uiso 1 1 calc R . .
C10 C 0.8038(3) 0.21408(16) 1.00458(12) 0.0199(4) Uani 1 1 d . . .
H10 H 0.8042 0.1570 1.0341 0.024 Uiso 1 1 calc R . .
C11 C 0.7637(3) 0.32483(16) 1.04844(12) 0.0178(4) Uani 1 1 d . . .
H11 H 0.7363 0.3454 1.1093 0.021 Uiso 1 1 calc R . .
C12 C 0.7320(3) 0.56480(16) 0.60572(12) 0.0160(4) Uani 1 1 d . . .
C13 C 0.8023(3) 0.36797(15) 0.51699(12) 0.0152(4) Uani 1 1 d . . .
C14 C 0.8799(3) 0.17356(16) 0.45658(12) 0.0183(4) Uani 1 1 d . . .
H14 H 0.9133 0.1048 0.4667 0.022 Uiso 1 1 calc R . .
C15 C 0.8638(3) 0.17795(16) 0.37119(12) 0.0189(4) Uani 1 1 d . . .
H15 H 0.8887 0.1136 0.3216 0.023 Uiso 1 1 calc R . .
C16 C 0.8100(3) 0.27904(16) 0.35853(12) 0.0181(4) Uani 1 1 d . . .
H16 H 0.7942 0.2826 0.2994 0.022 Uiso 1 1 calc R . .
C17 C 0.7794(3) 0.37396(16) 0.43046(12) 0.0165(4) Uani 1 1 d . . .
H17 H 0.7431 0.4427 0.4212 0.020 Uiso 1 1 calc R . .
S1 S 0.21120(6) 0.42477(4) 0.74275(3) 0.01408(12) Uani 1 1 d . . .
O3 O 0.2607(2) 0.54178(11) 0.73442(9) 0.0211(3) Uani 1 1 d . . .
O4 O -0.00607(18) 0.37662(11) 0.71945(8) 0.0174(3) Uani 1 1 d . . .
O5 O 0.28494(19) 0.42209(11) 0.83054(8) 0.0190(3) Uani 1 1 d . . .
C18 C 0.3309(3) 0.32639(16) 0.66193(12) 0.0193(4) Uani 1 1 d . . .
H18A H 0.3042 0.3361 0.6034 0.029 Uiso 1 1 calc R . .
H18B H 0.2785 0.2442 0.6570 0.029 Uiso 1 1 calc R . .
H18C H 0.4766 0.3443 0.6805 0.029 Uiso 1 1 calc R . .
S2 S 0.78431(7) 0.04698(4) 0.63700(3) 0.01552(12) Uani 1 1 d . . .
O6 O 0.6724(2) 0.14252(11) 0.64008(9) 0.0234(3) Uani 1 1 d . . .
O7 O 0.7867(2) 0.01577(12) 0.71812(9) 0.0253(3) Uani 1 1 d . . .
O8 O 0.98505(19) 0.07081(11) 0.61136(9) 0.0228(3) Uani 1 1 d . . .
C19 C 0.6530(3) -0.08099(16) 0.54946(12) 0.0205(4) Uani 1 1 d . . .
H19A H 0.7196 -0.1490 0.5459 0.031 Uiso 1 1 calc R . .
H19B H 0.6528 -0.0664 0.4920 0.031 Uiso 1 1 calc R . .
H19C H 0.5138 -0.0983 0.5620 0.031 Uiso 1 1 calc R . .
C20 C 0.3225(3) 0.13978(17) 0.80114(13) 0.0244(4) Uani 1 1 d . . .
H20A H 0.2036 0.1209 0.7567 0.037 Uiso 1 1 calc R . .
H20B H 0.4432 0.1303 0.7700 0.037 Uiso 1 1 calc R . .
H20C H 0.3359 0.2222 0.8419 0.037 Uiso 1 1 calc R . .
C21 C 0.3002(3) 0.05994(18) 0.85255(14) 0.0272(4) Uani 1 1 d . . .
N6 N 0.2807(4) -0.0029(2) 0.89253(16) 0.0516(6) 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
_geom_angle_publ_flag
C5 N1 C1 117.46(15) . . ?
C6 N2 C7 126.63(15) . . ?
C7 N3 C11 122.18(15) . . ?
C13 N4 C12 127.62(15) . . ?
C14 N5 C13 123.14(15) . . ?
N1 C1 C2 123.34(17) . . ?
N1 C1 C12 116.38(15) . . ?
C2 C1 C12 120.27(16) . . ?
C1 C2 C3 118.48(17) . . ?
C4 C3 C2 119.14(17) . . ?
C3 C4 C5 117.92(17) . . ?
N1 C5 C4 123.65(16) . . ?
N1 C5 C6 116.50(15) . . ?
C4 C5 C6 119.84(16) . . ?
O1 C6 N2 123.33(16) . . ?
O1 C6 C5 122.21(16) . . ?
N2 C6 C5 114.46(15) . . ?
N3 C7 N2 120.54(16) . . ?
N3 C7 C8 119.02(16) . . ?
N2 C7 C8 120.44(16) . . ?
C9 C8 C7 119.33(17) . . ?
C8 C9 C10 120.57(17) . . ?
C11 C10 C9 118.37(17) . . ?
N3 C11 C10 120.52(16) . . ?
O2 C12 N4 125.07(16) . . ?
O2 C12 C1 122.47(16) . . ?
N4 C12 C1 112.45(15) . . ?
N5 C13 N4 115.24(15) . . ?
N5 C13 C17 118.20(16) . . ?
N4 C13 C17 126.55(16) . . ?
N5 C14 C15 120.03(17) . . ?
C14 C15 C16 118.43(17) . . ?
C17 C16 C15 120.96(17) . . ?
C16 C17 C13 119.17(17) . . ?
O3 S1 O5 113.10(8) . . ?
O3 S1 O4 111.76(7) . . ?
O5 S1 O4 111.47(7) . . ?
O3 S1 C18 107.51(8) . . ?
O5 S1 C18 106.97(8) . . ?
O4 S1 C18 105.54(8) . . ?
O7 S2 O8 112.72(8) . . ?
O7 S2 O6 113.54(8) . . ?
O8 S2 O6 111.65(8) . . ?
O7 S2 C19 105.85(9) . . ?
O8 S2 C19 106.28(8) . . ?
O6 S2 C19 106.13(9) . . ?
N6 C21 C20 179.3(3) . . ?
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
N1 C5 1.334(2) . ?
N1 C1 1.337(2) . ?
N2 C6 1.369(2) . ?
N2 C7 1.376(2) . ?
N3 C7 1.346(2) . ?
N3 C11 1.357(2) . ?
N4 C13 1.370(2) . ?
N4 C12 1.375(2) . ?
N5 C14 1.348(2) . ?
N5 C13 1.354(2) . ?
O1 C6 1.221(2) . ?
O2 C12 1.218(2) . ?
C1 C2 1.386(3) . ?
C1 C12 1.505(2) . ?
C2 C3 1.387(3) . ?
C3 C4 1.386(3) . ?
C4 C5 1.393(3) . ?
C5 C6 1.500(2) . ?
C7 C8 1.395(3) . ?
C8 C9 1.371(3) . ?
C9 C10 1.401(3) . ?
C10 C11 1.365(3) . ?
C13 C17 1.394(2) . ?
C14 C15 1.367(3) . ?
C15 C16 1.392(3) . ?
C16 C17 1.377(3) . ?
S1 O3 1.4540(13) . ?
S1 O5 1.4565(13) . ?
S1 O4 1.4729(13) . ?
S1 C18 1.7647(18) . ?
S2 O7 1.4502(13) . ?
S2 O8 1.4556(14) . ?
S2 O6 1.4569(13) . ?
S2 C19 1.7706(18) . ?
C20 C21 1.449(3) . ?
C21 N6 1.135(3) . ?
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
_geom_torsion_publ_flag
C5 N1 C1 C2 1.3(3) . . . . ?
C5 N1 C1 C12 -177.98(15) . . . . ?
N1 C1 C2 C3 -0.2(3) . . . . ?
C12 C1 C2 C3 178.98(16) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C1 N1 C5 C4 -1.3(3) . . . . ?
C1 N1 C5 C6 177.32(15) . . . . ?
C3 C4 C5 N1 0.3(3) . . . . ?
C3 C4 C5 C6 -178.26(16) . . . . ?
C7 N2 C6 O1 5.6(3) . . . . ?
C7 N2 C6 C5 -174.48(16) . . . . ?
N1 C5 C6 O1 -170.35(16) . . . . ?
C4 C5 C6 O1 8.3(3) . . . . ?
N1 C5 C6 N2 9.7(2) . . . . ?
C4 C5 C6 N2 -171.60(16) . . . . ?
C11 N3 C7 N2 178.29(16) . . . . ?
C11 N3 C7 C8 -1.5(3) . . . . ?
C6 N2 C7 N3 -5.7(3) . . . . ?
C6 N2 C7 C8 174.08(17) . . . . ?
N3 C7 C8 C9 1.2(3) . . . . ?
N2 C7 C8 C9 -178.58(16) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C7 N3 C11 C10 0.8(3) . . . . ?
C9 C10 C11 N3 0.2(3) . . . . ?
C13 N4 C12 O2 -0.8(3) . . . . ?
C13 N4 C12 C1 178.96(16) . . . . ?
N1 C1 C12 O2 173.29(16) . . . . ?
C2 C1 C12 O2 -6.0(3) . . . . ?
N1 C1 C12 N4 -6.5(2) . . . . ?
C2 C1 C12 N4 174.23(16) . . . . ?
C14 N5 C13 N4 -177.95(16) . . . . ?
C14 N5 C13 C17 2.4(3) . . . . ?
C12 N4 C13 N5 -178.55(16) . . . . ?
C12 N4 C13 C17 1.0(3) . . . . ?
C13 N5 C14 C15 -0.7(3) . . . . ?
N5 C14 C15 C16 -1.4(3) . . . . ?
C14 C15 C16 C17 1.9(3) . . . . ?
C15 C16 C17 C13 -0.2(3) . . . . ?
N5 C13 C17 C16 -1.9(3) . . . . ?
N4 C13 C17 C16 178.51(17) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659165
2 PubChem 139091444
