#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/10/4501062.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_4501062
loop_
_publ_author_name
'Stilinović, Vladimir'
'Kaitner, Branko'
_publ_section_title
;
 Hydrogen Bonding in Pyridinium Picrates: From Discrete Ion Pairs to 3D
 Networks
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4110
_journal_paper_doi               10.1021/cg200684x
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety         'C6 H2 N3 O7, C9 H8 N'
_chemical_formula_sum            'C15 H10 N4 O7'
_chemical_formula_weight         358.27
_chemical_name_systematic
;
quinolinium picrate
;
_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_date             2010-09-20T17:15:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 95.388(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4255(5)
_cell_length_b                   6.8019(3)
_cell_length_c                   17.9141(9)
_cell_measurement_reflns_used    629
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      32.0
_cell_measurement_theta_min      4.6
_cell_volume                     1507.36(12)
_computing_cell_refinement
;
CrysAlis RED 170 (Oxford Diffraction Poland Sp., 2003)
;
_computing_data_collection
;
CrysAlis CCD 170 (Oxford Diffraction Poland Sp., 2003)
;
_computing_data_reduction
;
CrysAlis RED 170 (Oxford Diffraction Poland Sp., 2003)
;
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
;
WinGX (Farrugia, 1999) 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_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  0.0156
_diffrn_reflns_av_unetI/netI     0.026
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5396
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         4.2
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.593
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2599
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.926
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0770P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1118
_reflns_number_gt                1797
_reflns_number_total             2599
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200684x_si_002.cif
_cod_data_source_block           quin
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4501062
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
N4 N 0.39904(12) 0.1479(2) 0.28981(9) 0.0391(4) Uani 1 1 d .
C8 C 0.47864(16) 0.1572(3) 0.41408(11) 0.0545(5) Uani 1 1 d .
H8 H 0.4705 0.1623 0.4651 0.065 Uiso 1 1 calc R
C15 C 0.49789(13) 0.1468(2) 0.26143(9) 0.0351(4) Uani 1 1 d .
C14 C 0.50478(14) 0.1440(3) 0.18367(10) 0.0412(4) Uani 1 1 d .
H14 H 0.4426 0.1443 0.1504 0.049 Uiso 1 1 calc R
C10 C 0.59189(13) 0.1484(2) 0.31227(10) 0.0397(4) Uani 1 1 d .
C9 C 0.57924(15) 0.1533(3) 0.38940(11) 0.0502(5) Uani 1 1 d .
H9 H 0.64 0.1538 0.4239 0.06 Uiso 1 1 calc R
C11 C 0.69344(14) 0.1456(3) 0.28233(12) 0.0509(5) Uani 1 1 d .
H11 H 0.7567 0.1467 0.3145 0.061 Uiso 1 1 calc R
C13 C 0.60452(15) 0.1408(3) 0.15792(11) 0.0506(5) Uani 1 1 d .
H13 H 0.6101 0.1382 0.1065 0.061 Uiso 1 1 calc R
C7 C 0.38867(15) 0.1535(3) 0.36200(11) 0.0493(5) Uani 1 1 d .
H7 H 0.3199 0.155 0.3785 0.059 Uiso 1 1 calc R
C12 C 0.69904(15) 0.1413(3) 0.20745(12) 0.0556(5) Uani 1 1 d .
H12 H 0.7662 0.1386 0.1885 0.067 Uiso 1 1 calc R
H4 H 0.3424(16) 0.148(3) 0.2562(11) 0.049(5) Uiso 1 1 d .
N1 N 0.76445(12) 0.6307(2) 0.48719(9) 0.0499(4) Uani 1 1 d .
O5 O 1.20898(11) 0.9071(2) 0.45097(9) 0.0665(4) Uani 1 1 d .
O7 O 0.84576(12) 0.7094(3) 0.20740(8) 0.0849(6) Uani 1 1 d .
O2 O 0.67328(11) 0.6771(3) 0.46286(9) 0.0959(7) Uani 1 1 d .
O3 O 0.78529(12) 0.5551(2) 0.54838(9) 0.0708(5) Uani 1 1 d .
O6 O 1.01383(14) 0.7697(3) 0.21851(9) 0.1036(7) Uani 1 1 d .
C2 C 0.85408(13) 0.6803(2) 0.44339(10) 0.0372(4) Uani 1 1 d .
C1 C 0.83578(13) 0.6763(2) 0.36227(10) 0.0396(4) Uani 1 1 d .
N3 N 0.92876(14) 0.7426(3) 0.24605(9) 0.0545(4) Uani 1 1 d U
O1 O 0.74914(10) 0.6174(2) 0.32874(7) 0.0566(4) Uani 1 1 d .
C4 C 1.03531(13) 0.7866(2) 0.44424(10) 0.0394(4) Uani 1 1 d .
N2 N 1.13650(12) 0.8394(2) 0.48531(10) 0.0488(4) Uani 1 1 d .
C6 C 0.93020(14) 0.7406(2) 0.32734(10) 0.0406(4) Uani 1 1 d U
C3 C 0.94943(13) 0.7259(2) 0.48295(10) 0.0394(4) Uani 1 1 d .
H3 H 0.9571 0.7167 0.535 0.047 Uiso 1 1 calc R
C5 C 1.02490(14) 0.7958(2) 0.36687(10) 0.0433(4) Uani 1 1 d .
H5 H 1.0824 0.8397 0.3416 0.052 Uiso 1 1 calc R
O4 O 1.14607(11) 0.8136(2) 0.55350(8) 0.0649(4) 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 0 '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 0.006 '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
C7 N4 C15 122.63(16)
C7 N4 H4 121.8(12)
C15 N4 H4 115.5(12)
C9 C8 C7 119.11(18)
C9 C8 H8 120.4
C7 C8 H8 120.4
N4 C15 C14 120.51(15)
N4 C15 C10 118.41(15)
C14 C15 C10 121.08(15)
C13 C14 C15 118.57(17)
C13 C14 H14 120.7
C15 C14 H14 120.7
C9 C10 C15 118.18(16)
C9 C10 C11 123.93(17)
C15 C10 C11 117.90(17)
C8 C9 C10 120.61(17)
C8 C9 H9 119.7
C10 C9 H9 119.7
C12 C11 C10 120.48(17)
C12 C11 H11 119.8
C10 C11 H11 119.8
C14 C13 C12 121.31(18)
C14 C13 H13 119.3
C12 C13 H13 119.3
N4 C7 C8 121.05(18)
N4 C7 H7 119.5
C8 C7 H7 119.5
C11 C12 C13 120.66(17)
C11 C12 H12 119.7
C13 C12 H12 119.7
O2 N1 O3 123.00(16)
O2 N1 C2 118.62(17)
O3 N1 C2 118.23(15)
C3 C2 C1 125.04(15)
C3 C2 N1 116.38(15)
C1 C2 N1 118.58(15)
O1 C1 C6 125.86(16)
O1 C1 C2 122.35(15)
C6 C1 C2 111.74(15)
O7 N3 O6 121.40(18)
O7 N3 C6 120.09(16)
O6 N3 C6 118.42(17)
C5 C4 C3 120.71(16)
C5 C4 N2 119.73(16)
C3 C4 N2 119.56(16)
O5 N2 O4 123.01(16)
O5 N2 C4 118.93(17)
O4 N2 C4 118.06(15)
C5 C6 C1 123.48(16)
C5 C6 N3 116.41(16)
C1 C6 N3 120.08(16)
C2 C3 C4 118.74(16)
C2 C3 H3 120.6
C4 C3 H3 120.6
C6 C5 C4 120.13(16)
C6 C5 H5 119.9
C4 C5 H5 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N4 C7 1.312(2)
N4 C15 1.373(2)
N4 H4 0.882(19)
C8 C9 1.365(3)
C8 C7 1.387(3)
C8 H8 0.93
C15 C14 1.404(2)
C15 C10 1.412(2)
C14 C13 1.362(2)
C14 H14 0.93
C10 C9 1.406(3)
C10 C11 1.417(2)
C9 H9 0.93
C11 C12 1.350(3)
C11 H11 0.93
C13 C12 1.404(3)
C13 H13 0.93
C7 H7 0.93
C12 H12 0.93
N1 O2 1.217(2)
N1 O3 1.216(2)
N1 C2 1.461(2)
O5 N2 1.227(2)
O7 N3 1.208(2)
O6 N3 1.222(2)
C2 C3 1.358(2)
C2 C1 1.450(2)
C1 O1 1.249(2)
C1 C6 1.448(2)
N3 C6 1.455(2)
C4 C5 1.381(3)
C4 C3 1.389(2)
C4 N2 1.441(2)
N2 O4 1.229(2)
C6 C5 1.368(2)
C3 H3 0.93
C5 H5 0.93
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 451676
2 PubChem 139144599
