#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/41/2014144.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_2014144
loop_
_publ_author_name
'Büyükgüngör, Orhan'
'Odabaşoğlu, Mustafa'
'Albayrak, Çiğdem'
'Lönnecke, Peter'
_publ_section_title
;
 2-Aminopyridinium--fumarate--fumaric acid (2/1/1)
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o470
_journal_page_last               o472
_journal_paper_doi               10.1107/S0108270104010546
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          '2C5 H7 N2 +, C4 H4 O4 2-, C4 H2 O4'
_chemical_formula_moiety         '2C5 H7 N2 +, C4 H4 O4 2-, C4 H2 O4'
_chemical_formula_sum            'C18 H20 N4 O8'
_chemical_formula_weight         420.38
_chemical_name_systematic
;
2-aminopyridinium--fumarate--fumaric acid (2/1/1)
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 102.484(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.4012(15)
_cell_length_b                   4.9254(7)
_cell_length_c                   19.162(3)
_cell_measurement_reflns_used    580
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      25.52
_cell_measurement_theta_min      2.21
_cell_volume                     958.5(2)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      210(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       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  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4856
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.9771
_exptl_absorpt_correction_T_min  0.9549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Blessing, 1995)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         1868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0423
_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)+(0.0603P)²+0.2244P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1122
_reflns_number_gt                1639
_reflns_number_total             1868
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fr1480.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2014144
_cod_database_fobs_code          2014144
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_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.28839(11) 0.9060(2) 0.48461(6) 0.0313(3) Uani d . 1 . . O
O2 0.39950(12) 0.8202(3) 0.39912(6) 0.0402(3) Uani d . 1 . . O
O3 0.01125(10) 0.6021(2) 0.37236(5) 0.0301(3) Uani d . 1 . . O
O4 0.17449(10) 0.3064(2) 0.40659(6) 0.0302(3) Uani d . 1 . . O
N1 0.24904(12) 0.3967(3) 0.27916(7) 0.0267(3) Uani d . 1 . . N
N2 0.10764(13) 0.7615(3) 0.24931(8) 0.0326(3) Uani d . 1 . . N
C1 0.19504(14) 0.5899(3) 0.23203(8) 0.0254(3) Uani d . 1 . . C
C2 0.23543(15) 0.6033(3) 0.16620(8) 0.0283(3) Uani d . 1 . . C
C3 0.32862(15) 0.4276(3) 0.15312(8) 0.0305(4) Uani d . 1 . . C
C4 0.38426(16) 0.2320(3) 0.20416(9) 0.0310(4) Uani d . 1 . . C
C5 0.34181(15) 0.2197(3) 0.26617(9) 0.0294(4) Uani d . 1 . . C
C6 0.37754(14) 0.7767(3) 0.45769(8) 0.0256(3) Uani d . 1 . . C
C7 0.45086(15) 0.5695(3) 0.50735(8) 0.0280(3) Uani d . 1 . . C
C8 0.07828(13) 0.4483(3) 0.41789(7) 0.0236(3) Uani d . 1 . . C
C9 0.04570(14) 0.4256(3) 0.49011(8) 0.0263(3) Uani d . 1 . . C
H1 0.2197(17) 0.376(4) 0.3234(11) 0.037(5) Uiso d . 1 . . H
H2 0.1965(18) 0.739(4) 0.1345(10) 0.035(5) Uiso d . 1 . . H
H3 0.3597(17) 0.441(4) 0.1088(10) 0.035(5) Uiso d . 1 . . H
H4 0.4514(18) 0.113(4) 0.1967(10) 0.037(5) Uiso d . 1 . . H
H5 0.3702(18) 0.093(4) 0.3045(11) 0.041(5) Uiso d . 1 . . H
H7 0.4234(18) 0.551(4) 0.5512(10) 0.044(5) Uiso d . 1 . . H
H9 0.0969(17) 0.291(4) 0.5218(9) 0.035(5) Uiso d . 1 . . H
H10 0.245(2) 1.048(5) 0.4535(13) 0.063(7) Uiso d . 1 . . H
H11 0.0822(19) 0.746(4) 0.2907(11) 0.039(5) Uiso d . 1 . . H
H12 0.0697(18) 0.892(4) 0.2164(11) 0.038(5) Uiso d . 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0374(6) 0.0325(6) 0.0257(6) 0.0098(5) 0.0107(4) 0.0042(5)
O2 0.0466(7) 0.0479(8) 0.0310(6) 0.0162(6) 0.0193(5) 0.0160(5)
O3 0.0339(6) 0.0354(6) 0.0228(5) 0.0080(5) 0.0096(4) 0.0042(5)
O4 0.0342(6) 0.0333(6) 0.0268(6) 0.0099(5) 0.0148(4) 0.0047(5)
N1 0.0316(7) 0.0277(7) 0.0221(6) -0.0026(5) 0.0090(5) 0.0032(5)
N2 0.0366(7) 0.0355(8) 0.0288(7) 0.0067(6) 0.0137(6) 0.0060(6)
C1 0.0256(7) 0.0252(8) 0.0255(7) -0.0046(6) 0.0057(6) -0.0001(6)
C2 0.0315(8) 0.0302(8) 0.0236(7) -0.0019(6) 0.0068(6) 0.0061(6)
C3 0.0342(8) 0.0353(9) 0.0240(8) -0.0043(7) 0.0104(6) -0.0001(7)
C4 0.0338(8) 0.0295(8) 0.0309(8) 0.0015(7) 0.0098(6) 0.0003(7)
C5 0.0331(8) 0.0265(8) 0.0287(8) 0.0002(6) 0.0072(6) 0.0050(7)
C6 0.0268(7) 0.0251(8) 0.0256(7) -0.0018(6) 0.0076(6) 0.0018(6)
C7 0.0320(8) 0.0287(8) 0.0239(7) -0.0002(6) 0.0077(6) 0.0037(6)
C8 0.0252(7) 0.0237(7) 0.0228(7) 0.0001(6) 0.0072(6) -0.0007(6)
C9 0.0267(7) 0.0309(8) 0.0221(7) 0.0024(6) 0.0070(6) 0.0021(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
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'
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
_geom_angle_publ_flag
C6 O1 H10 . 112.6(13) ?
C1 N1 C5 . 122.56(13) ?
C1 N1 H1 . 119.8(11) ?
C5 N1 H1 . 117.6(11) ?
C1 N2 H11 . 121.0(13) ?
C1 N2 H12 . 118.9(12) ?
H11 N2 H12 . 120.0(17) ?
N2 C1 N1 . 119.23(14) ?
N2 C1 C2 . 122.77(14) ?
N1 C1 C2 . 117.99(14) ?
C3 C2 C1 . 119.65(14) ?
C3 C2 H2 . 124.1(11) ?
C1 C2 H2 . 116.2(11) ?
C2 C3 C4 . 120.64(14) ?
C2 C3 H3 . 120.0(10) ?
C4 C3 H3 . 119.3(10) ?
C5 C4 C3 . 118.52(15) ?
C5 C4 H4 . 119.8(11) ?
C3 C4 H4 . 121.7(11) ?
C4 C5 N1 . 120.61(14) ?
C4 C5 H5 . 126.5(11) ?
N1 C5 H5 . 112.9(11) ?
O2 C6 O1 . 124.50(14) y
O2 C6 C7 . 122.70(14) ?
O1 C6 C7 . 112.80(13) ?
C7 C7 C6 3_666 122.45(18) ?
C7 C7 H7 3_666 122.5(12) ?
C6 C7 H7 . 115.0(12) ?
O3 C8 O4 . 123.61(13) y
O3 C8 C9 . 119.15(13) ?
O4 C8 C9 . 117.24(12) ?
C9 C9 C8 3_566 123.03(18) ?
C9 C9 H9 3_566 122.0(10) ?
C8 C9 H9 . 115.0(10) ?
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
O1 C6 . 1.3182(18) y
O1 H10 . 0.97(2) ?
O2 C6 . 1.2118(19) y
O3 C8 . 1.2482(17) y
O4 C8 . 1.2771(17) y
N1 C1 . 1.3479(19) y
N1 C5 . 1.363(2) y
N1 H1 . 0.97(2) ?
N2 C1 . 1.334(2) y
N2 H11 . 0.89(2) ?
N2 H12 . 0.93(2) ?
C1 C2 . 1.415(2) ?
C2 C3 . 1.362(2) ?
C2 H2 . 0.94(2) ?
C3 C4 . 1.405(2) ?
C3 H3 . 0.974(18) ?
C4 C5 . 1.355(2) ?
C4 H4 . 0.946(19) ?
C5 H5 . 0.96(2) ?
C6 C7 . 1.488(2) ?
C7 C7 3_666 1.311(3) y
C7 H7 . 0.95(2) ?
C8 C9 . 1.498(2) ?
C9 C9 3_566 1.319(3) y
C9 H9 . 0.978(18) ?
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 O4 . 0.97(2) 1.79(2) 2.7533(16) 174.2(17)
N2 H11 O3 . 0.89(2) 2.00(2) 2.8643(18) 163.2(19)
N2 H12 O3 2 0.93(2) 2.01(2) 2.9211(19) 166.0(17)
O1 H10 O4 . 0.97(2) 1.64(3) 2.6004(15) 175(2)
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
_geom_torsion_publ_flag
C5 N1 C1 N2 . -177.97(14) y
C5 N1 C1 C2 . 1.3(2) ?
N2 C1 C2 C3 . 177.66(15) ?
N1 C1 C2 C3 . -1.5(2) ?
C1 C2 C3 C4 . 0.5(2) ?
C2 C3 C4 C5 . 0.9(2) ?
C3 C4 C5 N1 . -1.2(2) ?
C1 N1 C5 C4 . 0.1(2) ?
O2 C6 C7 C7 3_666 3.9(3) y
O1 C6 C7 C7 3_666 -175.69(19) y
O3 C8 C9 C9 3_566 -4.5(3) y
O4 C8 C9 C9 3_566 175.54(18) y
