#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/77/2227784.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_2227784
loop_
_publ_author_name
'Li, Yan-jun'
_publ_section_title
;
 3-Aminopyridinium picrate
;
_journal_coeditor_code           LH5128
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2680
_journal_paper_doi               10.1107/S1600536810037190
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C5 H7 N2 +, C6 H2 N3 O7 -'
_chemical_formula_moiety         'C5 H7 N2 +, C6 H2 N3 O7 -'
_chemical_formula_sum            'C11 H9 N5 O7'
_chemical_formula_weight         323.23
_chemical_name_systematic
;
3-Aminopyridinium picrate
;
_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                 102.117(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2174(8)
_cell_length_b                   13.5842(13)
_cell_length_c                   11.8218(12)
_cell_measurement_reflns_used    1100
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      20.38
_cell_measurement_theta_min      2.31
_cell_volume                     1290.2(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD'
_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  0.0719
_diffrn_reflns_av_sigmaI/netI    0.0718
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14192
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.9972
_exptl_absorpt_correction_T_min  0.9389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.242
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1351
_refine_ls_R_factor_gt           0.0595
_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)+(0.0663P)²+0.0975P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1619
_reflns_number_gt                1391
_reflns_number_total             2804
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5128.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2227784
_cod_database_fobs_code          2227784
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
C C1 0.8262(3) 0.49045(18) 0.2590(2) 0.0390(7) Uani d . 1 . .
C C2 0.8816(3) 0.45022(19) 0.1686(2) 0.0401(7) Uani d . 1 . .
H H2 0.8614 0.4819 0.0973 0.048 Uiso calc R 1 . .
C C3 0.9673(3) 0.36279(18) 0.1827(2) 0.0378(7) Uani d . 1 . .
C C4 1.0039(3) 0.31637(19) 0.2881(2) 0.0388(7) Uani d . 1 . .
H H4 1.0636 0.2577 0.2967 0.047 Uiso calc R 1 . .
C C5 0.9518(3) 0.35703(19) 0.3805(2) 0.0388(7) Uani d . 1 . .
C C6 0.8524(4) 0.4466(2) 0.3728(2) 0.0428(7) Uani d . 1 . .
C C7 0.5593(4) 0.6203(2) 0.7181(2) 0.0449(7) Uani d . 1 . .
C C8 0.5870(4) 0.5718(2) 0.8241(2) 0.0474(8) Uani d . 1 . .
H H8 0.5482 0.5994 0.8855 0.057 Uiso calc R 1 . .
C C9 0.6702(4) 0.4844(2) 0.8392(3) 0.0532(8) Uani d . 1 . .
H H9 0.6866 0.4527 0.9104 0.064 Uiso calc R 1 . .
C C10 0.7300(4) 0.4426(2) 0.7507(3) 0.0531(8) Uani d . 1 . .
H H10 0.7872 0.3831 0.7605 0.064 Uiso calc R 1 . .
C C11 0.6221(4) 0.5750(2) 0.6304(2) 0.0470(8) Uani d . 1 . .
H H11 0.6070 0.6043 0.5578 0.056 Uiso calc R 1 . .
N N1 0.7366(3) 0.58418(19) 0.2352(3) 0.0562(7) Uani d . 1 . .
N N2 1.0162(3) 0.31865(19) 0.0837(2) 0.0498(7) Uani d . 1 . .
N N3 0.9978(4) 0.3051(2) 0.4890(2) 0.0569(7) Uani d . 1 . .
N N4 0.4760(4) 0.7061(2) 0.7014(3) 0.0684(9) Uani d . 1 . .
N N5 0.7032(3) 0.4902(2) 0.6502(2) 0.0511(7) Uani d . 1 . .
O O1 0.6984(4) 0.61237(17) 0.1355(3) 0.0962(10) Uani d . 1 . .
O O2 0.6942(4) 0.6267(2) 0.3121(2) 0.1179(12) Uani d . 1 . .
O O3 0.9816(3) 0.36138(17) -0.00931(18) 0.0755(8) Uani d . 1 . .
O O4 1.0901(3) 0.24022(17) 0.09581(19) 0.0736(7) Uani d . 1 . .
O O5 1.1054(3) 0.24169(18) 0.49917(19) 0.0764(8) Uani d . 1 . .
O O6 0.9316(3) 0.3268(2) 0.5696(2) 0.0916(9) Uani d . 1 . .
O O7 0.7949(3) 0.48236(16) 0.45224(19) 0.0770(8) Uani d . 1 . .
H H4A 0.455(5) 0.730(3) 0.634(3) 0.092 Uiso d . 1 . .
H H4B 0.436(5) 0.731(3) 0.757(3) 0.092 Uiso d . 1 . .
H H5 0.749(4) 0.465(2) 0.592(3) 0.092 Uiso 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
C2 C1 C6 . . 123.8(2) ?
C2 C1 N1 . . 115.8(3) ?
C6 C1 N1 . . 120.4(3) ?
C1 C2 C3 . . 120.0(3) ?
C1 C2 H2 . . 120.0 ?
C3 C2 H2 . . 120.0 ?
C4 C3 C2 . . 121.1(2) ?
C4 C3 N2 . . 120.0(2) ?
C2 C3 N2 . . 118.9(2) ?
C5 C4 C3 . . 119.5(3) ?
C5 C4 H4 . . 120.2 ?
C3 C4 H4 . . 120.2 ?
C4 C5 N3 . . 116.4(3) ?
C4 C5 C6 . . 123.4(2) ?
N3 C5 C6 . . 120.2(3) ?
O7 C6 C1 . . 122.6(3) ?
O7 C6 C5 . . 125.4(3) ?
C1 C6 C5 . . 112.0(2) ?
N4 C7 C8 . . 121.6(3) ?
N4 C7 C11 . . 122.0(3) ?
C8 C7 C11 . . 116.4(3) ?
C9 C8 C7 . . 120.8(3) ?
C9 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C8 C9 C10 . . 120.8(3) ?
C8 C9 H9 . . 119.6 ?
C10 C9 H9 . . 119.6 ?
N5 C10 C9 . . 117.5(3) ?
N5 C10 H10 . . 121.2 ?
C9 C10 H10 . . 121.2 ?
N5 C11 C7 . . 120.2(3) ?
N5 C11 H11 . . 119.9 ?
C7 C11 H11 . . 119.9 ?
O2 N1 O1 . . 122.0(3) ?
O2 N1 C1 . . 119.3(3) ?
O1 N1 C1 . . 118.4(3) ?
O4 N2 O3 . . 122.4(2) ?
O4 N2 C3 . . 118.9(3) ?
O3 N2 C3 . . 118.6(3) ?
O5 N3 O6 . . 121.5(3) ?
O5 N3 C5 . . 118.8(3) ?
O6 N3 C5 . . 119.7(3) ?
C7 N4 H4A . . 118(3) ?
C7 N4 H4B . . 119(3) ?
H4A N4 H4B . . 122(4) ?
C11 N5 C10 . . 124.2(3) ?
C11 N5 H5 . . 117(2) ?
C10 N5 H5 . . 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
C1 C2 . 1.361(3) ?
C1 C6 . 1.446(4) ?
C1 N1 . 1.468(3) ?
C2 C3 . 1.373(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.372(4) ?
C3 N2 . 1.445(3) ?
C4 C5 . 1.371(3) ?
C4 H4 . 0.9300 ?
C5 N3 . 1.443(3) ?
C5 C6 . 1.457(4) ?
C6 O7 . 1.236(3) ?
C7 N4 . 1.345(4) ?
C7 C8 . 1.392(4) ?
C7 C11 . 1.394(4) ?
C8 C9 . 1.364(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.369(4) ?
C9 H9 . 0.9300 ?
C10 N5 . 1.329(4) ?
C10 H10 . 0.9300 ?
C11 N5 . 1.328(4) ?
C11 H11 . 0.9300 ?
N1 O2 . 1.190(3) ?
N1 O1 . 1.216(3) ?
N2 O4 . 1.220(3) ?
N2 O3 . 1.223(3) ?
N3 O5 . 1.222(3) ?
N3 O6 . 1.229(3) ?
N4 H4A . 0.85(4) ?
N4 H4B . 0.86(4) ?
N5 H5 . 0.91(3) ?
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
N5 H5 O7 . 0.91(3) 1.79(3) 2.607(3) 148(3)
N5 H5 O6 . 0.91(3) 2.46(3) 3.179(4) 136(3)
N4 H4B O6 2_656 0.86(4) 2.48(4) 3.119(4) 132(3)
N4 H4A O3 2_655 0.85(4) 2.44(4) 3.172(4) 145(3)
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
C6 C1 C2 C3 . . . . 0.3(4) ?
N1 C1 C2 C3 . . . . 179.8(2) ?
C1 C2 C3 C4 . . . . -2.4(4) ?
C1 C2 C3 N2 . . . . 176.4(2) ?
C2 C3 C4 C5 . . . . 1.1(4) ?
N2 C3 C4 C5 . . . . -177.7(2) ?
C3 C4 C5 N3 . . . . -178.8(2) ?
C3 C4 C5 C6 . . . . 2.4(4) ?
C2 C1 C6 O7 . . . . -176.9(3) ?
N1 C1 C6 O7 . . . . 3.6(4) ?
C2 C1 C6 C5 . . . . 2.8(4) ?
N1 C1 C6 C5 . . . . -176.7(2) ?
C4 C5 C6 O7 . . . . 175.5(3) ?
N3 C5 C6 O7 . . . . -3.2(4) ?
C4 C5 C6 C1 . . . . -4.1(4) ?
N3 C5 C6 C1 . . . . 177.1(2) ?
N4 C7 C8 C9 . . . . 179.3(3) ?
C11 C7 C8 C9 . . . . -0.5(4) ?
C7 C8 C9 C10 . . . . 0.6(4) ?
C8 C9 C10 N5 . . . . -0.2(4) ?
N4 C7 C11 N5 . . . . -179.8(3) ?
C8 C7 C11 N5 . . . . 0.0(4) ?
C2 C1 N1 O2 . . . . -175.1(3) ?
C6 C1 N1 O2 . . . . 4.4(4) ?
C2 C1 N1 O1 . . . . 9.8(4) ?
C6 C1 N1 O1 . . . . -170.7(3) ?
C4 C3 N2 O4 . . . . -0.1(4) ?
C2 C3 N2 O4 . . . . -178.9(3) ?
C4 C3 N2 O3 . . . . 179.8(3) ?
C2 C3 N2 O3 . . . . 1.0(4) ?
C4 C5 N3 O5 . . . . 14.6(4) ?
C6 C5 N3 O5 . . . . -166.5(3) ?
C4 C5 N3 O6 . . . . -167.1(3) ?
C6 C5 N3 O6 . . . . 11.8(4) ?
C7 C11 N5 C10 . . . . 0.4(4) ?
C9 C10 N5 C11 . . . . -0.3(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21425225
