#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/75/2017598.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_2017598
loop_
_publ_author_name
'Perpétuo, Genivaldo Julio'
'Janczak, Jan'
_publ_section_title
;
 Hydrogen-bonded networks in 5-chloropyridin-2-amine--fumaric acid
 (2/1) and 2-aminopyridinium <small>DL</small>-malate
;
_journal_coeditor_code           FA3217
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o225
_journal_page_last               o228
_journal_paper_doi               10.1107/S010827011000987X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C5 H7 N2 +, C4 H5 O5 -'
_chemical_formula_moiety         'C5 H7 N2 +, C4 H5 O5 -'
_chemical_formula_sum            'C9 H12 N2 O5'
_chemical_formula_weight         228.21
_chemical_name_common
;
2-aminopyridinium DL-malate
;
_chemical_name_systematic
;
2-aminopyridinium DL-3-carboxy-2-hydroxypropanoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.85(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6190(15)
_cell_length_b                   7.4730(15)
_cell_length_c                   19.042(4)
_cell_measurement_reflns_used    782
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.38
_cell_measurement_theta_min      2.93
_cell_volume                     1068.2(4)
_computing_cell_refinement
;
CrysAlis Red (Oxford Diffraction, 2008)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2008)
;
_computing_data_reduction
;
CrysAlis Red (Oxford Diffraction, 2008)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg &  Putz, 2006)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'KUMA KM-4 with area CCD detector'
_diffrn_measurement_method       ω-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  0.0551
_diffrn_reflns_av_sigmaI/netI    0.0970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13230
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         29.38
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9738
_exptl_absorpt_correction_T_min  0.9622
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(CrysAlis Red; Oxford Diffraction, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      1.41
_exptl_crystal_density_method    flotation
_exptl_crystal_description       paralellepiped
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2730
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0593
_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)+(0.0190P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0836
_reflns_number_gt                1436
_reflns_number_total             2730
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fa3217.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2017598
_cod_database_fobs_code          2017598
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_disorder_assembly
_atom_site_disorder_group
O O1 0.61017(17) 0.9701(2) 0.19686(7) 0.0453(5) Uani d . 1 . .
O O2 0.75745(19) 1.0347(2) 0.30518(7) 0.0452(5) Uani d . 1 . .
C C1 0.7518(3) 0.9826(3) 0.24309(12) 0.0347(6) Uani d . 1 . .
C C2 0.9294(3) 0.9411(3) 0.21877(11) 0.0330(6) Uani d . 1 . .
H H2 1.0112 0.8864 0.2583 0.049 Uiso calc R 1 . .
O O5 0.9133(2) 0.8278(2) 0.15820(8) 0.0415(5) Uani d . 1 . .
H H5O 0.877(3) 0.733(3) 0.1724(13) 0.062 Uiso d . 1 . .
C C3 1.0070(3) 1.1179(3) 0.19883(11) 0.0370(6) Uani d . 1 . .
H H3A 0.9285 1.1676 0.1580 0.056 Uiso calc R 1 . .
H H3B 1.0095 1.2009 0.2382 0.056 Uiso calc R 1 . .
C C4 1.1904(3) 1.1041(3) 0.18136(13) 0.0392(6) Uani d . 1 . .
O O3 1.30418(18) 1.0295(3) 0.23311(8) 0.0505(5) Uani d . 1 . .
H H3O 1.410(3) 1.019(3) 0.2227(12) 0.076 Uiso d . 1 . .
O O4 1.2308(2) 1.1593(3) 0.12726(8) 0.0716(6) Uani d . 1 . .
N N1 0.4824(3) 0.7760(3) 0.07924(10) 0.0514(7) Uani d . 1 . .
H H1 0.554(3) 0.825(3) 0.1174(10) 0.062 Uiso d . 1 . .
C C5 0.5430(4) 0.7742(4) 0.01713(11) 0.0449(7) Uani d . 1 . .
C C6 0.4270(4) 0.7034(3) -0.04227(13) 0.0540(8) Uani d . 1 . .
H H6 0.4627 0.6990 -0.0866 0.065 Uiso calc R 1 . .
C C7 0.2649(4) 0.6424(4) -0.03479(13) 0.0591(8) Uani d . 1 . .
H H7 0.1894 0.5968 -0.0743 0.071 Uiso calc R 1 . .
C C8 0.2083(4) 0.6461(4) 0.03078(14) 0.0704(9) Uani d . 1 . .
H H8 0.0971 0.6016 0.0357 0.084 Uiso calc R 1 . .
C C9 0.3190(4) 0.7163(4) 0.08746(13) 0.0664(9) Uani d . 1 . .
H H9 0.2831 0.7234 0.1317 0.080 Uiso calc R 1 . .
N N2 0.7034(3) 0.8375(4) 0.01534(10) 0.0564(6) Uani d D 1 . .
H H1N 0.778(3) 0.874(3) 0.0566(7) 0.085 Uiso d D 1 . .
H H2N 0.751(3) 0.831(4) -0.0263(6) 0.085 Uiso d D 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
_geom_angle_publ_flag
O2 C1 O1 . . 124.7(2) ?
O2 C1 C2 . . 117.58(19) ?
O1 C1 C2 . . 117.57(19) ?
O5 C2 C3 . . 107.38(17) ?
O5 C2 C1 . . 114.04(17) ?
C3 C2 C1 . . 107.43(18) ?
O5 C2 H2 . . 109.3 ?
C3 C2 H2 . . 109.3 ?
C1 C2 H2 . . 109.3 ?
C2 O5 H5O . . 103.6(17) ?
C4 C3 C2 . . 114.4(2) ?
C4 C3 H3A . . 108.7 ?
C2 C3 H3A . . 108.7 ?
C4 C3 H3B . . 108.7 ?
C2 C3 H3B . . 108.7 ?
H3A C3 H3B . . 107.6 ?
O4 C4 O3 . . 123.7(2) ?
O4 C4 C3 . . 123.7(2) ?
O3 C4 C3 . . 112.5(2) ?
C4 O3 H3O . . 112.6(16) ?
C5 N1 C9 . . 124.0(2) ?
C5 N1 H1 . . 117.3(13) ?
C9 N1 H1 . . 118.6(13) ?
N2 C5 N1 . . 118.7(2) ?
N2 C5 C6 . . 124.7(2) ?
N1 C5 C6 . . 116.5(3) ?
C7 C6 C5 . . 120.1(3) ?
C7 C6 H6 . . 120.0 ?
C5 C6 H6 . . 120.0 ?
C6 C7 C8 . . 121.3(3) ?
C6 C7 H7 . . 119.4 ?
C8 C7 H7 . . 119.4 ?
C9 C8 C7 . . 118.5(3) ?
C9 C8 H8 . . 120.8 ?
C7 C8 H8 . . 120.8 ?
C8 C9 N1 . . 119.6(2) ?
C8 C9 H9 . . 120.2 ?
N1 C9 H9 . . 120.2 ?
C5 N2 H1N . . 121.3(15) ?
C5 N2 H2N . . 120.3(15) ?
H1N N2 H2N . . 118(2) ?
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 C1 . 1.274(2) ?
O2 C1 . 1.239(2) ?
C1 C2 . 1.535(3) ?
C2 O5 . 1.419(2) ?
C2 C3 . 1.522(3) ?
C2 H2 . 0.9800 ?
O5 H5O . 0.82(2) ?
C3 C4 . 1.495(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 O4 . 1.198(2) ?
C4 O3 . 1.319(2) ?
O3 H3O . 0.86(2) ?
N1 C5 . 1.341(3) ?
N1 C9 . 1.356(3) ?
N1 H1 . 0.91(2) ?
C5 N2 . 1.316(3) ?
C5 C6 . 1.414(3) ?
C6 C7 . 1.347(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.389(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.356(3) ?
C8 H8 . 0.9300 ?
C9 H9 . 0.9300 ?
N2 H1N . 0.93(2) ?
N2 H2N . 0.93(2) ?
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
O5 H5O O2 2_645 0.82(2) 1.89(2) 2.699(2) 167(2) y
O3 H3O O1 1_655 0.86(2) 1.72(2) 2.581(2) 172(3) y
N1 H1 O1 . 0.91(2) 1.85(2) 2.706(2) 156(2) y
N2 H1N O5 . 0.93(2) 2.061(13) 2.911(2) 152(2) y
N2 H2N O4 3_775 0.93(2) 1.951(8) 2.845(3) 161(2) y
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 C1 C2 O5 . . . . 159.66(19) ?
O1 C1 C2 O5 . . . . -24.0(3) ?
O2 C1 C2 C3 . . . . -81.5(2) ?
O1 C1 C2 C3 . . . . 94.8(2) ?
O5 C2 C3 C4 . . . . -63.3(2) ?
C1 C2 C3 C4 . . . . 173.68(18) ?
C2 C3 C4 O4 . . . . 126.6(3) ?
C2 C3 C4 O3 . . . . -55.4(3) ?
C9 N1 C5 N2 . . . . 179.3(3) ?
C9 N1 C5 C6 . . . . -0.6(4) ?
N2 C5 C6 C7 . . . . -179.8(3) ?
N1 C5 C6 C7 . . . . 0.1(4) ?
C5 C6 C7 C8 . . . . -0.4(4) ?
C6 C7 C8 C9 . . . . 1.2(5) ?
C7 C8 C9 N1 . . . . -1.7(4) ?
C5 N1 C9 C8 . . . . 1.5(4) ?
