#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/86/2018690.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_2018690
loop_
_publ_author_name
'Lyakhov, Alexander S.'
'Ivashkevich, Ludmila S.'
'Survilo, Vladimir L.'
'Kipnis, Alexander M.'
'Trukhachova, Tatjana V.'
_publ_section_title
;
 2-Ethyl-6-methylpyridin-3-ol and its salt
 bis(2-ethyl-3-hydroxy-6-methylpyridinium) succinate
;
_journal_coeditor_code           YF3016
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o365
_journal_page_last               o368
_journal_paper_doi               10.1107/S0108270112035901
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '2C8 H12 N O + , C4 H4 O4 2-'
_chemical_formula_moiety         '2(C8 H12 N O), C4 H4 O4'
_chemical_formula_sum            'C20 H28 N2 O6'
_chemical_formula_weight         392.44
_chemical_name_systematic
;
bis(2-ethyl-3-hydroxy-6-methylpyridinium) succinate
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.3470(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.84450(10)
_cell_length_b                   13.4026(2)
_cell_length_c                   8.48480(10)
_cell_measurement_reflns_used    6266
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.55
_cell_measurement_theta_min      2.31
_cell_volume                     1001.41(2)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0156
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10139
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.31
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9717
_exptl_absorpt_correction_T_min  0.9508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.277
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2295
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0451
_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)+(0.0799P)²+0.2525P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1355
_reflns_number_gt                1999
_reflns_number_total             2295
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            yf3016.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018690
_cod_database_fobs_code          2018690
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_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 0.76284(11) 0.47793(8) 0.94007(12) 0.0333(3) Uani d . 1 1
H H1 0.7014(18) 0.4940(11) 1.0254(18) 0.040 Uiso d . 1 1
C C2 0.84014(13) 0.55289(9) 0.87948(14) 0.0320(3) Uani d . 1 1
C C3 0.94671(14) 0.53016(9) 0.77388(15) 0.0351(3) Uani d . 1 1
C C4 0.96533(16) 0.43072(10) 0.73254(17) 0.0428(3) Uani d . 1 1
H H4 1.0347 0.4139 0.6610 0.051 Uiso calc R 1 1
C C5 0.88148(16) 0.35722(10) 0.79703(17) 0.0432(3) Uani d . 1 1
H H5 0.8947 0.2909 0.7689 0.052 Uiso calc R 1 1
C C6 0.77793(15) 0.38104(9) 0.90306(15) 0.0376(3) Uani d . 1 1
C C7 0.80338(17) 0.65735(10) 0.92263(17) 0.0433(3) Uani d . 1 1
H H7A 0.8961 0.6963 0.9356 0.052 Uiso calc R 1 1
H H7B 0.7588 0.6574 1.0228 0.052 Uiso calc R 1 1
C C8 0.6937(2) 0.70496(13) 0.7967(2) 0.0684(5) Uani d . 1 1
H H8A 0.7337 0.6996 0.6957 0.103 Uiso calc R 1 1
H H8B 0.6804 0.7741 0.8218 0.103 Uiso calc R 1 1
H H8C 0.5976 0.6714 0.7928 0.103 Uiso calc R 1 1
C C9 0.6796(2) 0.30801(12) 0.9778(2) 0.0546(4) Uani d . 1 1
H H9A 0.6913 0.3165 1.0906 0.082 Uiso calc R 1 1
H H9B 0.7087 0.2414 0.9517 0.082 Uiso calc R 1 1
H H9C 0.5755 0.3190 0.9391 0.082 Uiso calc R 1 1
O O3 1.02594(12) 0.60541(8) 0.71789(13) 0.0500(3) Uani d . 1 1
H H3 1.119(3) 0.5807(16) 0.681(3) 0.075 Uiso d . 1 1
C C10 0.61981(14) 0.49835(9) 0.31790(15) 0.0370(3) Uani d . 1 1
C C11 0.49738(15) 0.52736(11) 0.42268(15) 0.0413(3) Uani d . 1 1
H H11A 0.5057 0.5983 0.4444 0.050 Uiso calc R 1 1
H H11B 0.3991 0.5158 0.3648 0.050 Uiso calc R 1 1
O O1 0.60252(14) 0.52691(10) 0.17777(12) 0.0614(4) Uani d . 1 1
O O2 0.72877(13) 0.44799(11) 0.37839(15) 0.0654(4) Uani d . 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
C2 N1 C6 . 124.55(11)
C2 N1 H1 . 117.4(9)
C6 N1 H1 . 117.6(9)
N1 C2 C3 . 118.76(11)
N1 C2 C7 . 118.54(10)
C3 C2 C7 . 122.64(11)
O3 C3 C4 . 123.59(11)
O3 C3 C2 . 118.09(11)
C4 C3 C2 . 118.32(12)
C5 C4 C3 . 120.28(12)
C5 C4 H4 . 119.9
C3 C4 H4 . 119.9
C4 C5 C6 . 120.56(12)
C4 C5 H5 . 119.7
C6 C5 H5 . 119.7
N1 C6 C5 . 117.50(12)
N1 C6 C9 . 117.41(12)
C5 C6 C9 . 125.08(13)
C2 C7 C8 . 111.23(13)
C2 C7 H7A . 109.4
C8 C7 H7A . 109.4
C2 C7 H7B . 109.4
C8 C7 H7B . 109.4
H7A C7 H7B . 108.0
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
C3 O3 H3 . 110.3(13)
O1 C10 O2 . 125.51(12)
O1 C10 C11 . 116.79(12)
O2 C10 C11 . 117.69(11)
C11 C11 C10 3_666 114.99(14)
C11 C11 H11A 3_666 108.5
C10 C11 H11A . 108.5
C11 C11 H11B 3_666 108.5
C10 C11 H11B . 108.5
H11A C11 H11B . 107.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C2 . 1.3441(16)
N1 C6 . 1.3455(16)
N1 H1 . 0.969(16)
C2 C3 . 1.3933(16)
C2 C7 . 1.4907(17)
C3 O3 . 1.3401(15)
C3 C4 . 1.3919(18)
C4 C5 . 1.377(2)
C4 H4 . 0.9300
C5 C6 . 1.3797(19)
C5 H5 . 0.9300
C6 C9 . 1.4896(19)
C7 C8 . 1.515(2)
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
O3 H3 . 0.97(2)
C10 O1 . 1.2449(16)
C10 O2 . 1.2472(18)
C10 C11 . 1.5145(16)
C11 C11 3_666 1.500(2)
C11 H11A . 0.9700
C11 H11B . 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
_geom_hbond_publ_flag
N1 H1 O1 1_556 0.969(16) 1.686(16) 2.6538(14) 176.6(14) yes
O3 H3 O2 3_766 0.97(2) 1.53(2) 2.4932(13) 175(2) yes
C5 H5 O3 2_746 0.93 2.58 3.4779(17) 162. yes
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 . -1.74(18)
C6 N1 C2 C7 . 175.61(12)
N1 C2 C3 O3 . -178.16(11)
C7 C2 C3 O3 . 4.60(19)
N1 C2 C3 C4 . 1.72(18)
C7 C2 C3 C4 . -175.51(12)
O3 C3 C4 C5 . 178.92(13)
C2 C3 C4 C5 . -1.0(2)
C3 C4 C5 C6 . 0.1(2)
C2 N1 C6 C5 . 0.86(19)
C2 N1 C6 C9 . -178.14(12)
C4 C5 C6 N1 . 0.0(2)
C4 C5 C6 C9 . 178.91(14)
N1 C2 C7 C8 . -96.77(15)
C3 C2 C7 C8 . 80.47(17)
O1 C10 C11 C11 3_666 166.38(16)
O2 C10 C11 C11 3_666 -13.5(2)
