#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/83/2018365.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2018365
loop_
_publ_author_name
'Lyakhov, Alexander S.'
'Ivashkevich, Ludmila S.'
'Survilo, Vladimir L.'
'Trukhachova, Tatjana V.'
_publ_section_title
;
 Two succinic acid derivatives of 2-ethyl-6-methylpyridin-3-ol
;
_journal_coeditor_code           YF3010
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o33
_journal_page_last               o36
_journal_paper_doi               10.1107/S0108270111054692
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C8 H12 N O + , 0.5C4 H4 O4 2- , 0.5C4 H6 O4'
_chemical_formula_moiety         'C8 H12 N O +, 0.5(C4 H4 O4 2-), 0.5(C4 H6 O4)'
_chemical_formula_sum            'C12 H17 N O5'
_chemical_formula_weight         255.27
_chemical_name_common
;
bis(2-ethyl-6-methyl-3-hydroxypyridinium) butanedioate--butanedioic acid (1/1)
;
_chemical_name_systematic
;
bis(2-ethyl-6-methyl-3-hydroxypyridinium) succinate--succinic acid (1/1)
;
_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           SHELXL97
_cell_angle_alpha                95.7470(10)
_cell_angle_beta                 103.9260(10)
_cell_angle_gamma                107.7160(10)
_cell_formula_units_Z            2
_cell_length_a                   7.3047(6)
_cell_length_b                   8.4660(7)
_cell_length_c                   11.7559(10)
_cell_measurement_reflns_used    2735
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.57
_cell_volume                     660.25(10)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω 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  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6220
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.57
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_correction_T_min  0.9610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.236
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0665P)²+0.1610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1283
_reflns_number_gt                2189
_reflns_number_total             2717
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            yf3010.cif
_cod_data_source_block           I
_cod_database_code               2018365
_cod_database_fobs_code          2018365
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
N N1 0.14960(17) 0.42043(15) 0.37481(10) 0.0384(3) Uani d . 1 1
H H1 0.0912 0.3733 0.3012 0.046 Uiso calc R 1 1
C C2 0.16956(19) 0.58313(18) 0.40600(12) 0.0346(3) Uani d . 1 1
C C3 0.2574(2) 0.65950(19) 0.52588(12) 0.0372(3) Uani d . 1 1
O O3 0.26961(18) 0.82004(14) 0.55682(9) 0.0498(3) Uani d . 1 1
H H3 0.2980 0.8452 0.6296 0.075 Uiso calc R 1 1
C C4 0.3273(2) 0.5662(2) 0.60597(13) 0.0449(4) Uani d . 1 1
H H4 0.3888 0.6157 0.6860 0.054 Uiso calc R 1 1
C C5 0.3060(2) 0.4013(2) 0.56741(15) 0.0477(4) Uani d . 1 1
H H5 0.3544 0.3404 0.6216 0.057 Uiso calc R 1 1
C C6 0.2138(2) 0.3249(2) 0.44960(15) 0.0441(4) Uani d . 1 1
C C7 0.1032(2) 0.6755(2) 0.31137(13) 0.0422(4) Uani d . 1 1
H H7A 0.0326 0.7440 0.3400 0.051 Uiso calc R 1 1
H H7B 0.0105 0.5945 0.2415 0.051 Uiso calc R 1 1
C C8 0.2791(3) 0.7883(2) 0.27663(16) 0.0550(4) Uani d . 1 1
H H8A 0.3747 0.8646 0.3464 0.082 Uiso calc R 1 1
H H8B 0.2318 0.8516 0.2201 0.082 Uiso calc R 1 1
H H8C 0.3418 0.7199 0.2415 0.082 Uiso calc R 1 1
C C9 0.1797(3) 0.1469(2) 0.3983(2) 0.0670(5) Uani d . 1 1
H H9A 0.0382 0.0862 0.3684 0.100 Uiso calc R 1 1
H H9B 0.2389 0.0949 0.4592 0.100 Uiso calc R 1 1
H H9C 0.2400 0.1447 0.3344 0.100 Uiso calc R 1 1
C C10 0.7209(2) 0.1343(2) 0.13892(13) 0.0439(4) Uani d . 1 1
O O101 0.88897(18) 0.24738(16) 0.15792(10) 0.0618(4) Uani d . 1 1
O O102 0.6442(2) 0.08687(18) 0.21770(10) 0.0704(4) Uani d . 1 1
C C11 0.6081(2) 0.0530(2) 0.01004(13) 0.0506(4) Uani d . 1 1
H H11A 0.6128 0.1412 -0.0371 0.061 Uiso calc R 1 1
H H11B 0.6763 -0.0173 -0.0189 0.061 Uiso calc R 1 1
C C12 0.2711(2) 0.3927(2) 0.05304(14) 0.0498(4) Uani d . 1 1
O O121 0.0812(2) 0.3133(2) -0.00103(12) 0.0906(6) Uani d . 1 1
H H121 0.0200 0.2922 0.0487 0.136 Uiso calc R 1 1
O O122 0.33909(19) 0.4171(2) 0.15904(11) 0.0766(5) Uani d . 1 1
C C13 0.3903(2) 0.4524(3) -0.03110(15) 0.0582(5) Uani d . 1 1
H H13A 0.3338 0.5251 -0.0758 0.070 Uiso calc R 1 1
H H13B 0.3788 0.3556 -0.0876 0.070 Uiso calc R 1 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 N1 C6 . . 125.30(13)
C2 N1 H1 . . 117.3
C6 N1 H1 . . 117.3
N1 C2 C3 . . 117.99(13)
N1 C2 C7 . . 119.05(12)
C3 C2 C7 . . 122.93(13)
O3 C3 C4 . . 123.86(13)
O3 C3 C2 . . 117.51(13)
C4 C3 C2 . . 118.64(14)
C3 O3 H3 . . 109.5
C5 C4 C3 . . 120.26(14)
C5 C4 H4 . . 119.9
C3 C4 H4 . . 119.9
C4 C5 C6 . . 120.86(14)
C4 C5 H5 . . 119.6
C6 C5 H5 . . 119.6
N1 C6 C5 . . 116.89(15)
N1 C6 C9 . . 117.60(16)
C5 C6 C9 . . 125.51(16)
C2 C7 C8 . . 111.91(13)
C2 C7 H7A . . 109.2
C8 C7 H7A . . 109.2
C2 C7 H7B . . 109.2
C8 C7 H7B . . 109.2
H7A C7 H7B . . 107.9
C7 C8 H8A . . 109.5
C7 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
C7 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
C6 C9 H9A . . 109.5
C6 C9 H9B . . 109.5
H9A C9 H9B . . 109.5
C6 C9 H9C . . 109.5
H9A C9 H9C . . 109.5
H9B C9 H9C . . 109.5
O102 C10 O101 . . 124.34(14)
O102 C10 C11 . . 118.87(13)
O101 C10 C11 . . 116.79(13)
C11 C11 C10 2_655 . 114.49(16)
C11 C11 H11A 2_655 . 108.6
C10 C11 H11A . . 108.6
C11 C11 H11B 2_655 . 108.6
C10 C11 H11B . . 108.6
H11A C11 H11B . . 107.6
O122 C12 O121 . . 122.67(16)
O122 C12 C13 . . 124.44(15)
O121 C12 C13 . . 112.87(14)
C12 O121 H121 . . 109.5
C12 C13 C13 . 2_665 113.19(17)
C12 C13 H13A . . 108.9
C13 C13 H13A 2_665 . 108.9
C12 C13 H13B . . 108.9
C13 C13 H13B 2_665 . 108.9
H13A C13 H13B . . 107.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.3431(19) yes
N1 C6 . 1.350(2) yes
N1 H1 . 0.8600 yes
C2 C3 . 1.3948(19) yes
C2 C7 . 1.493(2) yes
C3 O3 . 1.3413(19) yes
C3 C4 . 1.391(2) yes
O3 H3 . 0.8200 ?
C4 C5 . 1.374(2) yes
C4 H4 . 0.9300 ?
C5 C6 . 1.377(2) yes
C5 H5 . 0.9300 ?
C6 C9 . 1.488(3) yes
C7 C8 . 1.521(2) yes
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 O102 . 1.2327(19) yes
C10 O101 . 1.2587(18) yes
C10 C11 . 1.5142(19) yes
C11 C11 2_655 1.507(3) yes
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 O122 . 1.196(2) yes
C12 O121 . 1.305(2) yes
C12 C13 . 1.497(2) yes
O121 H121 . 0.8200 ?
C13 C13 2_665 1.511(3) yes
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O101 1_455 0.86 1.91 2.7367(16) 161
O3 H3 O102 2_666 0.82 1.74 2.5534(15) 176
O121 H121 O101 1_455 0.82 1.78 2.6020(18) 180
C4 H4 O122 2_666 0.93 2.46 3.1719(19) 134
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_site_symmetry_4
_geom_torsion
C6 N1 C2 C3 . -2.3(2)
C6 N1 C2 C7 . 175.89(13)
N1 C2 C3 O3 . -177.50(12)
C7 C2 C3 O3 . 4.4(2)
N1 C2 C3 C4 . 2.68(19)
C7 C2 C3 C4 . -175.44(13)
O3 C3 C4 C5 . 178.88(13)
C2 C3 C4 C5 . -1.3(2)
C3 C4 C5 C6 . -0.6(2)
C2 N1 C6 C5 . 0.4(2)
C2 N1 C6 C9 . -179.50(14)
C4 C5 C6 N1 . 1.1(2)
C4 C5 C6 C9 . -179.01(15)
N1 C2 C7 C8 . -101.27(16)
C3 C2 C7 C8 . 76.84(18)
O102 C10 C11 C11 2_655 12.4(3)
O101 C10 C11 C11 2_655 -167.5(2)
O122 C12 C13 C13 2_665 0.3(4)
O121 C12 C13 C13 2_665 178.8(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139061239
