#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/53/4025325.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_4025325
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         'C19 H19 N5 O2, 3(H2 O), 2(Br)'
_chemical_formula_sum            'C19 H25 Br2 N5 O5'
_chemical_formula_weight         563.26
_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                104.137(2)
_cell_angle_beta                 98.819(2)
_cell_angle_gamma                94.323(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4711(8)
_cell_length_b                   11.0507(12)
_cell_length_c                   14.3526(15)
_cell_measurement_reflns_used    8189
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.71
_cell_volume                     1127.6(2)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10689
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    3.635
_exptl_absorpt_correction_T_max  0.242
_exptl_absorpt_correction_T_min  0.167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.39
_refine_diff_density_max         1.371
_refine_diff_density_min         -1.052
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         3936
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0361
_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)+(0.0160P)²+6.5974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0957
_reflns_number_gt                3649
_reflns_number_total             3936
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100037m_si_007.cif
_cod_data_source_block           2jorgem
_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               4025325
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
Br1 Br 0.88065(5) 0.70501(4) 0.55767(3) 0.01670(12) Uani 1 1 d . . .
Br2 Br 0.48210(6) 0.66729(4) 0.23209(3) 0.02415(13) Uani 1 1 d . . .
N1 N 0.7817(5) 1.0322(3) 0.9953(3) 0.0167(7) Uani 1 1 d . . .
N2 N 0.6030(5) 0.8614(3) 0.8302(3) 0.0185(7) Uani 1 1 d D . .
H2' H 0.656(6) 0.935(2) 0.834(4) 0.028 Uiso 1 1 d D . .
N3 N 0.3906(5) 0.7596(3) 0.5743(3) 0.0218(8) Uani 1 1 d . . .
N4 N 0.9692(5) 1.2376(3) 0.9699(3) 0.0178(7) Uani 1 1 d D . .
H4' H 0.896(5) 1.185(4) 0.923(2) 0.027 Uiso 1 1 d D . .
N5 N 1.0743(5) 1.4360(3) 0.8136(3) 0.0199(8) Uani 1 1 d . . .
O1 O 0.4971(4) 0.7411(3) 0.9233(2) 0.0228(7) Uani 1 1 d . . .
O2 O 1.0761(4) 1.3036(3) 1.1350(2) 0.0224(7) Uani 1 1 d . . .
C1 C 0.8760(5) 1.1133(4) 1.0756(3) 0.0180(9) Uani 1 1 d . . .
C2 C 0.8824(6) 1.0970(4) 1.1692(3) 0.0203(9) Uani 1 1 d . . .
H2 H 0.9532 1.1564 1.2243 0.024 Uiso 1 1 calc R . .
C3 C 0.7825(6) 0.9914(4) 1.1798(3) 0.0213(9) Uani 1 1 d . . .
H3 H 0.7839 0.9771 1.2425 0.026 Uiso 1 1 calc R . .
C4 C 0.6808(6) 0.9072(4) 1.0973(3) 0.0204(9) Uani 1 1 d . . .
H4 H 0.6091 0.8351 1.1025 0.025 Uiso 1 1 calc R . .
C5 C 0.6865(5) 0.9308(4) 1.0069(3) 0.0169(8) Uani 1 1 d . . .
C6 C 0.5860(6) 0.8354(4) 0.9164(3) 0.0177(9) Uani 1 1 d . . .
C7 C 0.5250(6) 0.7808(4) 0.7393(3) 0.0181(9) Uani 1 1 d . . .
C8 C 0.4686(6) 0.8327(4) 0.6628(3) 0.0198(9) Uani 1 1 d . . .
H8 H 0.4852 0.9213 0.6730 0.024 Uiso 1 1 calc R . .
C9 C 0.3619(6) 0.6337(4) 0.5572(3) 0.0248(10) Uani 1 1 d . . .
H9 H 0.3017 0.5839 0.4949 0.030 Uiso 1 1 calc R . .
C10 C 0.4199(6) 0.5778(4) 0.6298(3) 0.0229(10) Uani 1 1 d . . .
H10 H 0.4019 0.4889 0.6172 0.027 Uiso 1 1 calc R . .
C11 C 0.5041(6) 0.6494(4) 0.7211(3) 0.0205(9) Uani 1 1 d . . .
H11 H 0.5474 0.6104 0.7709 0.025 Uiso 1 1 calc R . .
C12 C 0.9837(6) 1.2274(4) 1.0638(3) 0.0174(9) Uani 1 1 d . . .
C13 C 1.0589(6) 1.3351(4) 0.9411(3) 0.0172(8) Uani 1 1 d . . .
C14 C 0.9999(6) 1.3438(4) 0.8468(3) 0.0196(9) Uani 1 1 d . . .
H14 H 0.9055 1.2837 0.8051 0.024 Uiso 1 1 calc R . .
C15 C 1.2101(6) 1.5213(4) 0.8696(3) 0.0192(9) Uani 1 1 d . . .
H15 H 1.2624 1.5847 0.8443 0.023 Uiso 1 1 calc R . .
C16 C 1.2737(6) 1.5169(4) 0.9637(3) 0.0202(9) Uani 1 1 d . . .
H16 H 1.3691 1.5779 1.0034 0.024 Uiso 1 1 calc R . .
C17 C 1.1990(6) 1.4237(4) 1.0011(3) 0.0189(9) Uani 1 1 d . . .
H17 H 1.2423 1.4204 1.0661 0.023 Uiso 1 1 calc R . .
C18 C 0.3323(7) 0.8187(5) 0.4942(3) 0.0301(11) Uani 1 1 d . . .
H18A H 0.4011 0.7909 0.4415 0.045 Uiso 1 1 calc R . .
H18B H 0.3555 0.9103 0.5190 0.045 Uiso 1 1 calc R . .
H18C H 0.2017 0.7940 0.4692 0.045 Uiso 1 1 calc R . .
C19 C 1.0033(7) 1.4434(4) 0.7129(3) 0.0264(10) Uani 1 1 d . . .
H19A H 1.0177 1.5312 0.7099 0.040 Uiso 1 1 calc R . .
H19B H 0.8738 1.4102 0.6951 0.040 Uiso 1 1 calc R . .
H19C H 1.0715 1.3936 0.6672 0.040 Uiso 1 1 calc R . .
O31 O 0.7250(5) 0.0888(3) 0.7887(2) 0.0237(7) Uani 1 1 d D . .
H31A H 0.659(6) 0.145(4) 0.781(4) 0.036 Uiso 1 1 d D . .
H31B H 0.774(7) 0.070(5) 0.739(2) 0.036 Uiso 1 1 d D . .
O32 O 0.1246(5) 0.9823(3) 0.3698(3) 0.0357(8) Uani 1 1 d D . .
H32A H 0.030(5) 0.943(5) 0.377(5) 0.054 Uiso 1 1 d D . .
H32B H 0.130(9) 1.0607(8) 0.390(5) 0.054 Uiso 1 1 d D . .
O33 O 0.7902(7) 0.8728(4) 0.3876(3) 0.0556(12) Uani 1 1 d D . .
H33A H 0.800(11) 0.838(7) 0.434(4) 0.083 Uiso 1 1 d D . .
H33B H 0.712(8) 0.819(6) 0.347(4) 0.083 Uiso 1 1 d 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'
Br Br -0.2901 2.4595 '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
C1 N1 C5 117.2(4) . . ?
C6 N2 C7 123.3(4) . . ?
C8 N3 C9 121.4(4) . . ?
C8 N3 C18 119.4(4) . . ?
C9 N3 C18 119.2(4) . . ?
C12 N4 C13 125.1(4) . . ?
C15 N5 C14 121.4(4) . . ?
C15 N5 C19 119.6(4) . . ?
C14 N5 C19 119.0(4) . . ?
N1 C1 C2 123.7(4) . . ?
N1 C1 C12 117.9(4) . . ?
C2 C1 C12 118.4(4) . . ?
C3 C2 C1 118.2(4) . . ?
C4 C3 C2 119.0(4) . . ?
C3 C4 C5 118.3(4) . . ?
N1 C5 C4 123.6(4) . . ?
N1 C5 C6 117.8(4) . . ?
C4 C5 C6 118.6(4) . . ?
O1 C6 N2 124.0(4) . . ?
O1 C6 C5 120.3(4) . . ?
N2 C6 C5 115.8(4) . . ?
C8 C7 N2 118.6(4) . . ?
C8 C7 C11 118.1(4) . . ?
N2 C7 C11 123.3(4) . . ?
N3 C8 C7 121.0(4) . . ?
N3 C9 C10 119.7(4) . . ?
C9 C10 C11 120.6(4) . . ?
C10 C11 C7 119.0(4) . . ?
O2 C12 N4 124.4(4) . . ?
O2 C12 C1 120.6(4) . . ?
N4 C12 C1 115.0(4) . . ?
C14 C13 C17 118.6(4) . . ?
C14 C13 N4 116.7(4) . . ?
C17 C13 N4 124.6(4) . . ?
N5 C14 C13 120.9(4) . . ?
N5 C15 C16 120.0(4) . . ?
C15 C16 C17 120.3(4) . . ?
C16 C17 C13 118.7(4) . . ?
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 C1 1.335(5) . ?
N1 C5 1.341(5) . ?
N2 C6 1.359(5) . ?
N2 C7 1.399(5) . ?
N3 C8 1.344(6) . ?
N3 C9 1.346(6) . ?
N3 C18 1.481(6) . ?
N4 C12 1.368(5) . ?
N4 C13 1.406(5) . ?
N5 C15 1.341(6) . ?
N5 C14 1.344(5) . ?
N5 C19 1.486(6) . ?
O1 C6 1.226(5) . ?
O2 C12 1.227(5) . ?
C1 C2 1.393(6) . ?
C1 C12 1.503(6) . ?
C2 C3 1.390(6) . ?
C3 C4 1.387(6) . ?
C4 C5 1.391(6) . ?
C5 C6 1.508(6) . ?
C7 C8 1.383(6) . ?
C7 C11 1.402(6) . ?
C9 C10 1.368(6) . ?
C10 C11 1.381(6) . ?
C13 C14 1.387(6) . ?
C13 C17 1.397(6) . ?
C15 C16 1.374(6) . ?
C16 C17 1.391(6) . ?
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 1.0(6) . . . . ?
C5 N1 C1 C12 179.9(3) . . . . ?
N1 C1 C2 C3 -1.2(6) . . . . ?
C12 C1 C2 C3 180.0(4) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C2 C3 C4 C5 1.4(6) . . . . ?
C1 N1 C5 C4 0.4(6) . . . . ?
C1 N1 C5 C6 -177.3(3) . . . . ?
C3 C4 C5 N1 -1.6(6) . . . . ?
C3 C4 C5 C6 176.1(4) . . . . ?
C7 N2 C6 O1 -2.2(7) . . . . ?
C7 N2 C6 C5 177.4(4) . . . . ?
N1 C5 C6 O1 180.0(4) . . . . ?
C4 C5 C6 O1 2.2(6) . . . . ?
N1 C5 C6 N2 0.4(5) . . . . ?
C4 C5 C6 N2 -177.4(4) . . . . ?
C6 N2 C7 C8 148.1(4) . . . . ?
C6 N2 C7 C11 -33.1(6) . . . . ?
C9 N3 C8 C7 1.0(6) . . . . ?
C18 N3 C8 C7 -179.9(4) . . . . ?
N2 C7 C8 N3 -179.1(4) . . . . ?
C11 C7 C8 N3 2.1(6) . . . . ?
C8 N3 C9 C10 -2.8(7) . . . . ?
C18 N3 C9 C10 178.1(4) . . . . ?
N3 C9 C10 C11 1.3(7) . . . . ?
C9 C10 C11 C7 1.8(7) . . . . ?
C8 C7 C11 C10 -3.4(6) . . . . ?
N2 C7 C11 C10 177.8(4) . . . . ?
C13 N4 C12 O2 0.8(7) . . . . ?
C13 N4 C12 C1 -179.2(4) . . . . ?
N1 C1 C12 O2 -178.4(4) . . . . ?
C2 C1 C12 O2 0.6(6) . . . . ?
N1 C1 C12 N4 1.7(5) . . . . ?
C2 C1 C12 N4 -179.4(4) . . . . ?
C12 N4 C13 C14 -167.3(4) . . . . ?
C12 N4 C13 C17 11.5(6) . . . . ?
C15 N5 C14 C13 1.2(6) . . . . ?
C19 N5 C14 C13 -178.4(4) . . . . ?
C17 C13 C14 N5 -0.5(6) . . . . ?
N4 C13 C14 N5 178.3(4) . . . . ?
C14 N5 C15 C16 -1.2(6) . . . . ?
C19 N5 C15 C16 178.4(4) . . . . ?
N5 C15 C16 C17 0.6(6) . . . . ?
C15 C16 C17 C13 0.1(6) . . . . ?
C14 C13 C17 C16 -0.1(6) . . . . ?
N4 C13 C17 C16 -178.8(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659168
2 PubChem 139091449
