#------------------------------------------------------------------------------
#$Date: 2017-07-25 12:49:51 +0300 (Tue, 25 Jul 2017) $
#$Revision: 199196 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/22/2242232.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_2242232
loop_
_publ_author_name
'Eya'ane Meva, Francois'
'Prior, Timothy John'
'Evans, David John'
'Mang, Emmanuel Roland'
_publ_section_title
;
 Crystal structures of N'-aminopyridine-2-carboximidamide and
 N'-{[1-(pyridin-2-yl)ethylidene]amino}pyridine-2-carboximidamide
;
_journal_coeditor_code           NK2236
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1021
_journal_page_last               1025
_journal_paper_doi               10.1107/S2056989017008416
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C6 H8 N4'
_chemical_formula_moiety         'C6 H8 N4'
_chemical_formula_sum            'C6 H8 N4'
_chemical_formula_weight         136.16
_chemical_name_systematic
;
N'-Aminopyridine-2-carboximidamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.631(19)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.6955(14)
_cell_length_b                   3.8408(5)
_cell_length_c                   14.592(4)
_cell_measurement_reflns_used    2199
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.55
_cell_measurement_theta_min      5.5
_cell_volume                     319.07(12)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2005)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2005)
;
_computing_data_reduction
;
scaled and merged with SORTAV (Blessing, 1987, 1989)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Stoe IPDS2'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0792
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2271
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.268
_diffrn_reflns_theta_min         2.793
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SORTAV; Blessing, 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       block
_exptl_crystal_F_000             144
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.368
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.874
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1407
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      0.870
_refine_ls_R_factor_all          0.1019
_refine_ls_R_factor_gt           0.0720
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1122P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1784
_refine_ls_wR_factor_ref         0.1928
_reflns_number_gt                806
_reflns_number_total             1407
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            nk2236sup1.cif
_cod_data_source_block           1
_cod_original_cell_volume        319.08(12)
_cod_database_code               2242232
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.981
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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_occupancy
C C1 0.3776(8) 0.3892(13) 0.8928(3) 0.0457(11) Uani d 1
H H1 0.494(4) 0.4064(14) 0.9427(17) 0.055 Uiso calc 1
C C2 0.1680(8) 0.2331(13) 0.9109(3) 0.0464(11) Uani d 1
H H2 0.1358(13) 0.143(3) 0.973(2) 0.056 Uiso calc 1
C C3 0.0007(9) 0.2040(13) 0.8396(3) 0.0462(11) Uani d 1
H H3 -0.152(5) 0.092(4) 0.8496(4) 0.055 Uiso calc 1
C C4 0.0545(8) 0.3357(12) 0.7545(3) 0.0423(11) Uani d 1
H H4 -0.060(4) 0.3176(14) 0.7027(17) 0.051 Uiso calc 1
C C5 0.2711(7) 0.4937(12) 0.7426(3) 0.0391(9) Uani d 1
C C6 0.3370(7) 0.6479(12) 0.6539(3) 0.0369(9) Uani d 1
N N1 0.4337(6) 0.5206(10) 0.8109(2) 0.0435(10) Uani d 1
N N2 0.5525(7) 0.7974(11) 0.6517(2) 0.0443(10) Uani d 1
N N3 0.1844(6) 0.6252(9) 0.5862(2) 0.0389(9) Uani d 1
N N4 0.2585(6) 0.7713(12) 0.5022(2) 0.0422(9) Uani d 1
H H4A 0.125(7) 0.840(13) 0.466(3) 0.063 Uiso d 1
H H2A 0.637(8) 0.830(16) 0.708(2) 0.063 Uiso d 1
H H2B 0.614(7) 0.954(13) 0.608(2) 0.063 Uiso d 1
H H4B 0.353(7) 0.970(12) 0.512(3) 0.065 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 C2 124.5(4)
N1 C1 H1 117.8
C2 C1 H1 117.8
C1 C2 C3 118.2(4)
C1 C2 H2 120.9
C3 C2 H2 120.9
C4 C3 C2 118.4(4)
C4 C3 H3 120.8
C2 C3 H3 120.8
C3 C4 C5 119.5(4)
C3 C4 H4 120.3
C5 C4 H4 120.3
N1 C5 C4 122.4(4)
N1 C5 C6 115.5(4)
C4 C5 C6 122.1(4)
N3 C6 N2 126.6(4)
N3 C6 C5 117.2(4)
N2 C6 C5 116.2(3)
C1 N1 C5 117.0(4)
C6 N2 H2A 118(3)
C6 N2 H2B 129(2)
H2A N2 H2B 108(3)
C6 N3 N4 114.8(4)
N3 N4 H4A 110(3)
N3 N4 H4B 111(3)
H4A N4 H4B 108(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.345(6)
C1 C2 1.368(7)
C1 H1 0.97(3)
C2 C3 1.395(7)
C2 H2 0.99(3)
C3 C4 1.383(6)
C3 H3 0.98(3)
C4 C5 1.390(6)
C4 H4 0.99(3)
C5 N1 1.345(5)
C5 C6 1.481(5)
C6 N3 1.300(5)
C6 N2 1.357(6)
N2 H2A 0.95(3)
N2 H2B 0.95(3)
N3 N4 1.424(5)
N4 H4A 0.95(3)
N4 H4B 0.94(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
N2 H2B N4 2_656 0.95(3) 2.16(3) 3.106(5) 174(4)
N4 H4B N4 2_656 0.94(3) 2.51(3) 3.357(6) 149(4)
N4 H4A N3 2_556 0.95(3) 2.19(4) 3.113(5) 162(4)

_cod_database_fobs_code 2242232
