#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:49:58 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301806 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/12/2231246.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_2231246
loop_
_publ_author_name
'Betz, Richard'
'Gerber, Thomas'
'Hosten, Eric'
'Schalekamp, Henk'
_publ_section_title
;
 Pyridine-2,3-diamine
;
_journal_coeditor_code           OM2449
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2154
_journal_paper_doi               10.1107/S1600536811029412
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C5 H7 N3'
_chemical_formula_moiety         'C5 H7 N3'
_chemical_formula_sum            'C5 H7 N3'
_chemical_formula_weight         109.14
_chemical_name_common            2,3-Diaminopyridine
_chemical_name_systematic
;
Pyridine-2,3-diamine
;
_space_group_IT_number           106
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4c -2ab'
_symmetry_space_group_name_H-M   'P 42 b c'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.4670(3)
_cell_length_b                   16.4670(3)
_cell_length_c                   3.9064(12)
_cell_measurement_reflns_used    5917
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.47
_cell_volume                     1059.3(3)
_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      200(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            9864
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.478
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.173
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     89
_refine_ls_number_reflns         754
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0360
_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)+(0.0428P)²+0.2489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0847
_reflns_number_gt                706
_reflns_number_total             754
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2449.cif
_cod_data_source_block           I
_cod_database_code               2231246
_cod_database_fobs_code          2231246
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x, z+1/2'
'-x, -y, z'
'y, -x, z+1/2'
'-x+1/2, y+1/2, z'
'-y+1/2, -x+1/2, z+1/2'
'x+1/2, -y+1/2, z'
'y+1/2, x+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_symmetry_multiplicity
N N1 0.20596(8) -0.05610(8) 0.9243(5) 0.0268(3) Uani d . 1 1
N N2 0.11296(8) 0.04458(9) 1.0621(5) 0.0271(3) Uani d . 1 1
H H21 0.1094(13) 0.0921(14) 1.156(8) 0.040(6) Uiso d . 1 1
H H22 0.0934(12) 0.0063(14) 1.184(7) 0.037(6) Uiso d . 1 1
N N3 0.21809(9) 0.16454(9) 0.7974(5) 0.0302(4) Uani d . 1 1
H H31 0.1677(13) 0.1730(12) 0.757(7) 0.033(5) Uiso d . 1 1
H H32 0.2471(12) 0.1946(12) 0.652(8) 0.038(6) Uiso d . 1 1
C C1 0.18758(9) 0.02266(9) 0.9286(5) 0.0225(4) Uani d . 1 1
C C2 0.23965(9) 0.08211(9) 0.7834(6) 0.0240(3) Uani d . 1 1
C C3 0.31167(10) 0.05570(10) 0.6425(5) 0.0283(4) Uani d . 1 1
H H3 0.3478 0.0938 0.5417 0.034 Uiso calc R 1 1
C C4 0.33173(10) -0.02631(11) 0.6469(6) 0.0307(4) Uani d . 1 1
H H4 0.3819 -0.0449 0.5556 0.037 Uiso calc R 1 1
C C5 0.27702(10) -0.07971(10) 0.7870(6) 0.0300(4) Uani d . 1 1
H H5 0.2900 -0.1359 0.7869 0.036 Uiso calc R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0256(7) 0.0250(7) 0.0298(8) 0.0002(5) -0.0024(7) 0.0000(7)
N2 0.0250(7) 0.0249(7) 0.0315(8) -0.0003(5) 0.0025(6) -0.0013(7)
N3 0.0276(7) 0.0256(7) 0.0374(9) -0.0023(5) -0.0009(8) 0.0039(8)
C1 0.0214(7) 0.0252(7) 0.0209(8) -0.0013(5) -0.0042(7) -0.0005(7)
C2 0.0238(7) 0.0267(7) 0.0217(7) -0.0032(5) -0.0040(7) 0.0003(8)
C3 0.0261(8) 0.0357(8) 0.0231(8) -0.0065(6) -0.0014(8) 0.0009(8)
C4 0.0242(7) 0.0411(9) 0.0268(9) 0.0024(6) 0.0012(8) -0.0044(9)
C5 0.0288(8) 0.0278(8) 0.0334(9) 0.0045(6) -0.0023(10) -0.0021(9)
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
C1 N1 C5 118.97(15)
C1 N2 H21 117.1(15)
C1 N2 H22 110.7(14)
H21 N2 H22 114(2)
C2 N3 H31 113.3(13)
C2 N3 H32 112.2(14)
H31 N3 H32 108(2)
N1 C1 N2 117.44(15)
N1 C1 C2 121.95(15)
N2 C1 C2 120.49(14)
C3 C2 N3 122.57(16)
C3 C2 C1 117.50(14)
N3 C2 C1 119.89(16)
C2 C3 C4 120.41(16)
C2 C3 H3 119.8
C4 C3 H3 119.8
C5 C4 C3 118.11(16)
C5 C4 H4 120.9
C3 C4 H4 120.9
N1 C5 C4 123.03(15)
N1 C5 H5 118.5
C4 C5 H5 118.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.332(2)
N1 C5 1.345(2)
N2 C1 1.383(2)
N2 H21 0.87(2)
N2 H22 0.85(2)
N3 C2 1.404(2)
N3 H31 0.86(2)
N3 H32 0.89(3)
C1 C2 1.420(2)
C2 C3 1.378(2)
C3 C4 1.390(2)
C3 H3 0.9500
C4 C5 1.373(3)
C4 H4 0.9500
C5 H5 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
N2 H21 N1 2 0.87(2) 2.32(2) 3.153(2) 161.2(19)
N2 H22 N2 4 0.85(2) 2.58(2) 3.4369(16) 175.9(18)
N3 H31 N1 2_554 0.86(2) 2.32(2) 3.115(2) 156(2)
N3 H32 N3 6_554 0.89(3) 2.47(2) 3.359(2) 175(2)
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
C5 N1 C1 N2 178.05(17)
C5 N1 C1 C2 1.9(3)
N1 C1 C2 C3 -1.4(3)
N2 C1 C2 C3 -177.42(18)
N1 C1 C2 N3 -179.3(2)
N2 C1 C2 N3 4.7(3)
N3 C2 C3 C4 177.43(19)
C1 C2 C3 C4 -0.4(3)
C2 C3 C4 C5 1.6(3)
C1 N1 C5 C4 -0.6(3)
C3 C4 C5 N1 -1.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9562
2 PubChem 9956
