#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/09/2220933.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_2220933
loop_
_publ_author_name
'Farnum, Gregory A.'
'LaDuca, Robert L.'
_publ_section_title
;
 4-(4-Pyridylamino)pyridinium perchlorate
;
_journal_coeditor_code           TK2362
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o423
_journal_paper_doi               10.1107/S1600536809003353
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C10 H10 N3 + , Cl O4 -'
_chemical_formula_moiety         'C10 H10 N3 + , Cl O4 -'
_chemical_formula_sum            'C10 H10 Cl N3 O4'
_chemical_formula_weight         271.66
_chemical_name_systematic
;
4-(4-Pyridylamino)pyridinium perchlorate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 101.9130(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6254(10)
_cell_length_b                   15.991(2)
_cell_length_c                   9.8358(13)
_cell_measurement_reflns_used    12615
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.5
_cell_volume                     1173.5(3)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'SMART (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'CrystalMaker (Palmer, 2007)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'Bruker SMART 1K'
_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  0.039
_diffrn_reflns_av_sigmaI/netI    0.027
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12615
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.47
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.337
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2728
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.052
_refine_ls_R_factor_gt           0.037
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0377P)²+0.7438P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.090
_refine_ls_wR_factor_ref         0.096
_reflns_number_gt                2165
_reflns_number_total             2728
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2362.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220933
_cod_database_fobs_code          2220933
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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.21340(6) 0.43473(3) 0.70621(5) 0.03353(14) Uani d . 1 . .
O O2 0.2109(9) 0.5174(3) 0.6429(5) 0.0405(12) Uani d P 0.50 A 1
O O3 0.3562(15) 0.4011(7) 0.6502(10) 0.057(2) Uani d P 0.50 A 1
O O4 0.2567(7) 0.4511(3) 0.8496(4) 0.0676(13) Uani d P 0.50 A 1
O O2A 0.2135(9) 0.4032(7) 0.8406(6) 0.169(4) Uani d P 0.50 A 2
O O3A 0.2109(10) 0.5200(5) 0.6966(10) 0.124(4) Uani d P 0.50 A 2
O O4A 0.3645(17) 0.3918(7) 0.6858(13) 0.095(4) Uani d P 0.50 A 2
O O1 0.0503(2) 0.39806(10) 0.6382(2) 0.0597(5) Uani d . 1 A .
N N1 0.0749(2) 0.35317(10) 0.28489(16) 0.0309(3) Uani d . 1 . .
H H1N -0.011(3) 0.3422(13) 0.325(2) 0.037 Uiso d . 1 . .
N N2 0.52241(19) 0.38493(9) 0.11764(16) 0.0280(3) Uani d . 1 . .
H H2N 0.579(3) 0.4301(13) 0.141(2) 0.034 Uiso d . 1 . .
N N3 0.8017(2) 0.22960(10) -0.10972(16) 0.0318(3) Uani d . 1 . .
C C1 0.1057(2) 0.29873(11) 0.18885(19) 0.0309(4) Uani d . 1 . .
H H1 0.0253 0.2534 0.1628 0.037 Uiso calc R 1 . .
C C2 0.2499(2) 0.30704(11) 0.12757(19) 0.0287(4) Uani d . 1 . .
H H2 0.2679 0.2687 0.0579 0.034 Uiso calc R 1 . .
C C3 0.3713(2) 0.37270(10) 0.16845(17) 0.0245(3) Uani d . 1 . .
C C4 0.3305(2) 0.43069(11) 0.26600(18) 0.0290(4) Uani d . 1 . .
H H4 0.4060 0.4777 0.2926 0.035 Uiso calc R 1 . .
C C5 0.1831(2) 0.41920(12) 0.32180(19) 0.0321(4) Uani d . 1 . .
H H5 0.1565 0.4583 0.3875 0.039 Uiso calc R 1 . .
C C6 0.6948(2) 0.19706(12) -0.03119(19) 0.0296(4) Uani d . 1 . .
H H6 0.6856 0.1379 -0.0275 0.036 Uiso calc R 1 . .
C C7 0.7192(2) 0.36562(11) -0.04063(19) 0.0303(4) Uani d . 1 . .
H H7 0.7312 0.4246 -0.0461 0.036 Uiso calc R 1 . .
C C8 0.6077(2) 0.33074(10) 0.04003(17) 0.0247(3) Uani d . 1 . .
C C9 0.5971(2) 0.24396(11) 0.04488(18) 0.0272(4) Uani d . 1 . .
H H9 0.5240 0.2175 0.0995 0.033 Uiso calc R 1 . .
C C10 0.8118(2) 0.31334(12) -0.11227(19) 0.0335(4) Uani d . 1 . .
H H10 0.8873 0.3381 -0.1667 0.040 Uiso calc R 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'
Cl Cl 0.1484 0.1585 '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
O3A Cl1 O4A . . 118.9(6) ?
O3A Cl1 O1 . . 112.5(3) ?
O4A Cl1 O1 . . 113.7(5) ?
O4 Cl1 O1 . . 123.6(2) ?
O3A Cl1 O2A . . 114.7(6) ?
O4A Cl1 O2A . . 96.8(7) ?
O1 Cl1 O2A . . 97.2(2) ?
O4 Cl1 O3 . . 114.8(5) ?
O1 Cl1 O3 . . 109.2(5) ?
O4 Cl1 O2 . . 103.9(3) ?
O1 Cl1 O2 . . 103.9(3) ?
O3 Cl1 O2 . . 96.9(5) ?
C1 N1 C5 . . 120.91(15) ?
C1 N1 H1N . . 117.0(14) ?
C5 N1 H1N . . 121.9(14) ?
C3 N2 C8 . . 129.38(15) ?
C3 N2 H2N . . 116.3(14) ?
C8 N2 H2N . . 114.1(14) ?
C6 N3 C10 . . 116.29(15) ?
N1 C1 C2 . . 121.48(17) ?
N1 C1 H1 . . 119.3 ?
C2 C1 H1 . . 119.3 ?
C1 C2 C3 . . 119.35(16) ?
C1 C2 H2 . . 120.3 ?
C3 C2 H2 . . 120.3 ?
N2 C3 C2 . . 124.10(15) ?
N2 C3 C4 . . 118.42(16) ?
C2 C3 C4 . . 117.46(15) ?
C5 C4 C3 . . 120.02(17) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
N1 C5 C4 . . 120.63(17) ?
N1 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
N3 C6 C9 . . 124.21(17) ?
N3 C6 H6 . . 117.9 ?
C9 C6 H6 . . 117.9 ?
C10 C7 C8 . . 119.04(16) ?
C10 C7 H7 . . 120.5 ?
C8 C7 H7 . . 120.5 ?
C9 C8 C7 . . 117.72(15) ?
C9 C8 N2 . . 124.18(15) ?
C7 C8 N2 . . 117.97(15) ?
C6 C9 C8 . . 118.78(15) ?
C6 C9 H9 . . 120.6 ?
C8 C9 H9 . . 120.6 ?
N3 C10 C7 . . 123.95(16) ?
N3 C10 H10 . . 118.0 ?
C7 C10 H10 . . 118.0 ?
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
Cl1 O3A . 1.366(7) ?
Cl1 O4A . 1.391(11) ?
Cl1 O4 . 1.405(4) ?
Cl1 O1 . 1.4125(15) ?
Cl1 O2A . 1.414(5) ?
Cl1 O3 . 1.423(8) ?
Cl1 O2 . 1.459(5) ?
N1 C1 . 1.341(2) ?
N1 C5 . 1.343(2) ?
N1 H1N . 0.85(2) ?
N2 C3 . 1.362(2) ?
N2 C8 . 1.400(2) ?
N2 H2N . 0.85(2) ?
N3 C6 . 1.338(2) ?
N3 C10 . 1.342(2) ?
C1 C2 . 1.366(2) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.402(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.414(2) ?
C4 C5 . 1.362(2) ?
C4 H4 . 0.9500 ?
C5 H5 . 0.9500 ?
C6 C9 . 1.381(2) ?
C6 H6 . 0.9500 ?
C7 C10 . 1.378(2) ?
C7 C8 . 1.394(2) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.391(2) ?
C9 H9 . 0.9500 ?
C10 H10 . 0.9500 ?
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 H1N N3 4_466 0.85(2) 2.04(2) 2.839(2) 157(2) y
N2 H2N O3A 3_666 0.85(2) 2.17(2) 2.873(8) 140.2(18) y
N2 H2N O4 3_666 0.85(2) 2.27(2) 3.098(5) 166.1(19) 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
C5 N1 C1 C2 . . . . 1.6(3) ?
N1 C1 C2 C3 . . . . 1.7(3) ?
C8 N2 C3 C2 . . . . -13.5(3) ?
C8 N2 C3 C4 . . . . 168.15(17) ?
C1 C2 C3 N2 . . . . 177.63(17) ?
C1 C2 C3 C4 . . . . -4.0(3) ?
N2 C3 C4 C5 . . . . -178.24(16) ?
C2 C3 C4 C5 . . . . 3.3(3) ?
C1 N1 C5 C4 . . . . -2.4(3) ?
C3 C4 C5 N1 . . . . -0.2(3) ?
C10 N3 C6 C9 . . . . 0.1(3) ?
C10 C7 C8 C9 . . . . 0.6(3) ?
C10 C7 C8 N2 . . . . 176.70(16) ?
C3 N2 C8 C9 . . . . -26.6(3) ?
C3 N2 C8 C7 . . . . 157.57(18) ?
N3 C6 C9 C8 . . . . 0.5(3) ?
C7 C8 C9 C6 . . . . -0.8(3) ?
N2 C8 C9 C6 . . . . -176.68(16) ?
C6 N3 C10 C7 . . . . -0.4(3) ?
C8 C7 C10 N3 . . . . 0.0(3) ?
