#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/13/2231370.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_2231370
loop_
_publ_author_name
'Schmitt, Bonell'
'Gerber, Thomas'
'Hosten, Eric'
'Betz, Richard'
_publ_section_title
;
 2-(Pyridin-2-ylamino)pyridinium thiocyanate acetonitrile monosolvate
;
_journal_coeditor_code           YA2142
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1981
_journal_page_last               o1982
_journal_paper_doi               10.1107/S1600536811026808
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C10 H10 N3 +, C N S -, C2 H3 N'
_chemical_formula_moiety         'C10 H10 N3 +, C N S -, C2 H3 N'
_chemical_formula_sum            'C13 H13 N5 S'
_chemical_formula_weight         271.34
_chemical_name_systematic
;
2-(Pyridin-2-ylamino)pyridinium thiocyanate acetonitrile monosolvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.8490(10)
_cell_angle_beta                 75.2110(10)
_cell_angle_gamma                81.3710(10)
_cell_formula_units_Z            2
_cell_length_a                   7.5450(3)
_cell_length_b                   7.8790(3)
_cell_length_c                   11.9900(4)
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.7
_cell_volume                     667.88(4)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_av_sigmaI/netI    0.015
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11528
_diffrn_reflns_theta_full        28.3
_diffrn_reflns_theta_max         28.3
_diffrn_reflns_theta_min         2.7
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.24
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3313
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.030
_refine_ls_R_factor_gt           0.028
_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)+(0.0442P)²+0.184P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.080
_refine_ls_wR_factor_ref         0.082
_reflns_number_gt                3113
_reflns_number_total             3313
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ya2142.cif
_cod_data_source_block           I
_cod_database_code               2231370
_cod_database_fobs_code          2231370
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
S S1 0.29241(3) 0.79739(3) 0.47166(2) 0.02280(9) Uani d . 1 1
N N1 0.25212(11) 0.56147(10) 0.07444(7) 0.01647(16) Uani d . 1 1
H H71 0.265(2) 0.6054(19) 0.1350(13) 0.031(3) Uiso d . 1 1
N N2 0.17025(10) 0.32447(10) 0.01896(7) 0.01588(16) Uani d . 1 1
N N3 0.31181(10) 0.59208(10) -0.13124(7) 0.01503(15) Uani d . 1 1
H H73 0.267(2) 0.484(2) -0.1156(13) 0.034(4) Uiso d . 1 1
N N10 0.30552(13) 0.68937(12) 0.26202(8) 0.02613(19) Uani d . 1 1
N N20 0.20385(13) 0.32594(13) 0.74643(8) 0.0283(2) Uani d . 1 1
C C1 0.30149(12) 0.73414(12) 0.34893(8) 0.01752(18) Uani d . 1 1
C C2 0.20307(13) 0.31158(12) 0.65393(9) 0.02028(19) Uani d . 1 1
C C3 0.19939(15) 0.29362(15) 0.53641(9) 0.0254(2) Uani d . 1 1
H H31 0.0713 0.3014 0.5301 0.038 Uiso calc R 1 1
H H32 0.2624 0.1799 0.5219 0.038 Uiso calc R 1 1
H H33 0.2620 0.3875 0.4781 0.038 Uiso calc R 1 1
C C11 0.18123(12) 0.39962(11) 0.10570(8) 0.01469(17) Uani d . 1 1
C C12 0.12748(12) 0.32258(12) 0.22524(8) 0.01750(18) Uani d . 1 1
H H12 0.1330 0.3817 0.2849 0.021 Uiso calc R 1 1
C C13 0.06646(13) 0.15854(13) 0.25345(8) 0.01970(19) Uani d . 1 1
H H13 0.0315 0.1012 0.3334 0.024 Uiso calc R 1 1
C C14 0.05640(13) 0.07707(12) 0.16347(9) 0.01948(18) Uani d . 1 1
H H14 0.0156 -0.0364 0.1809 0.023 Uiso calc R 1 1
C C15 0.10734(12) 0.16579(12) 0.04863(8) 0.01750(18) Uani d . 1 1
H H15 0.0974 0.1119 -0.0125 0.021 Uiso calc R 1 1
C C21 0.31450(11) 0.65375(11) -0.03559(8) 0.01480(17) Uani d . 1 1
C C22 0.38354(12) 0.81677(12) -0.05213(8) 0.01729(18) Uani d . 1 1
H H22 0.3894 0.8618 0.0138 0.021 Uiso calc R 1 1
C C23 0.44192(12) 0.90943(12) -0.16401(9) 0.01963(19) Uani d . 1 1
H H23 0.4863 1.0203 -0.1757 0.024 Uiso calc R 1 1
C C24 0.43654(13) 0.84134(12) -0.26181(8) 0.01979(19) Uani d . 1 1
H H24 0.4770 0.9051 -0.3396 0.024 Uiso calc R 1 1
C C25 0.37210(12) 0.68195(12) -0.24274(8) 0.01763(18) Uani d . 1 1
H H25 0.3693 0.6334 -0.3078 0.021 Uiso calc R 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'
S S 0.1246 0.1234 '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
C21 N1 C11 127.59(8)
C21 N1 H71 117.0(9)
C11 N1 H71 115.3(9)
C11 N2 C15 117.74(8)
C21 N3 C25 122.32(8)
C21 N3 H73 115.2(9)
C25 N3 H73 122.5(9)
N10 C1 S1 179.13(9)
N20 C2 C3 179.23(11)
C2 C3 H31 109.5
C2 C3 H32 109.5
H31 C3 H32 109.5
C2 C3 H33 109.5
H31 C3 H33 109.5
H32 C3 H33 109.5
N2 C11 N1 117.54(8)
N2 C11 C12 123.26(8)
N1 C11 C12 119.19(8)
C13 C12 C11 117.93(8)
C13 C12 H12 121.0
C11 C12 H12 121.0
C12 C13 C14 119.46(8)
C12 C13 H13 120.3
C14 C13 H13 120.3
C15 C14 C13 118.25(8)
C15 C14 H14 120.9
C13 C14 H14 120.9
N2 C15 C14 123.30(8)
N2 C15 H15 118.3
C14 C15 H15 118.3
N3 C21 N1 120.87(8)
N3 C21 C22 118.67(8)
N1 C21 C22 120.46(8)
C23 C22 C21 119.42(8)
C23 C22 H22 120.3
C21 C22 H22 120.3
C22 C23 C24 120.36(8)
C22 C23 H23 119.8
C24 C23 H23 119.8
C25 C24 C23 118.70(8)
C25 C24 H24 120.6
C23 C24 H24 120.6
N3 C25 C24 120.50(8)
N3 C25 H25 119.7
C24 C25 H25 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.6403(10)
N1 C21 1.3564(11)
N1 C11 1.3920(11)
N1 H71 0.903(15)
N2 C11 1.3334(11)
N2 C15 1.3433(11)
N3 C21 1.3492(11)
N3 C25 1.3606(11)
N3 H73 0.926(15)
N10 C1 1.1659(13)
N20 C2 1.1418(14)
C2 C3 1.4553(13)
C3 H31 0.9800
C3 H32 0.9800
C3 H33 0.9800
C11 C12 1.4029(12)
C12 C13 1.3773(13)
C12 H12 0.9500
C13 C14 1.3976(13)
C13 H13 0.9500
C14 C15 1.3802(13)
C14 H14 0.9500
C15 H15 0.9500
C21 C22 1.4116(12)
C22 C23 1.3696(13)
C22 H22 0.9500
C23 C24 1.4077(13)
C23 H23 0.9500
C24 C25 1.3644(13)
C24 H24 0.9500
C25 H25 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
N1 H71 N10 . 0.903(15) 1.901(15) 2.8020(11) 176.4(13)
N3 H73 N2 . 0.926(15) 1.861(15) 2.6068(11) 135.9(12)
N3 H73 N20 1_554 0.926(15) 2.456(15) 3.1199(12) 128.7(11)
C25 H25 S1 1_554 0.95 2.83 3.5192(9) 130
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
C15 N2 C11 N1 177.96(8)
C15 N2 C11 C12 -1.17(13)
C21 N1 C11 N2 -0.70(13)
C21 N1 C11 C12 178.47(8)
N2 C11 C12 C13 2.30(13)
N1 C11 C12 C13 -176.82(8)
C11 C12 C13 C14 -1.38(13)
C12 C13 C14 C15 -0.47(13)
C11 N2 C15 C14 -0.87(13)
C13 C14 C15 N2 1.68(14)
C25 N3 C21 N1 179.52(8)
C25 N3 C21 C22 -0.43(12)
C11 N1 C21 N3 0.43(14)
C11 N1 C21 C22 -179.63(8)
N3 C21 C22 C23 1.40(13)
N1 C21 C22 C23 -178.54(8)
C21 C22 C23 C24 -1.21(13)
C22 C23 C24 C25 0.04(14)
C21 N3 C25 C24 -0.76(13)
C23 C24 C25 N3 0.95(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656896
