##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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##############################################################################
data_I
_audit_creation_method     'SHELXL-2014/7'
_journal_date_recd_electronic     2017-07-14
_journal_date_accepted     2017-10-16
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2017
_journal_volume     73
_journal_issue     11
_journal_page_first     990
_journal_page_last     993
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229617014978
_journal_coeditor_code     QS3064
_publ_contact_author_name     'Jennifer A. Swift'
_publ_contact_author_address
;
Department of Chemistry
Georgetown University
37th and O Sts NW
Washington
DC 20057
USA
;
_publ_contact_author_email     jas2@georgetown.edu
_publ_contact_author_fax     '202-687-6209'
_publ_contact_author_phone     '202-687-5567'
_publ_section_title
;
A new polymorph of 2,6-diaminopyridine
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Hall, Victoria M.' .
;
Department of Chemistry
Georgetown University
37th and O Sts NW
Washington
DC 20057
USA
;
    'Bertke, Jeffery A.' .
;
Department of Chemistry
Georgetown University
37th and O Sts NW
Washington
DC 20057
USA
;
    'Swift, Jennifer A.' .
;
Department of Chemistry
Georgetown University
37th and O Sts NW
Washington
DC 20057
USA
;
_publ_section_synopsis
;
Sublimation yielded a new polymorph of 2,6-diaminopyridine, a common ingredient
in and a synthetic precursor to many colorants.
;
_chemical_name_systematic     'Pyridine-2,6-diamine'
_chemical_name_common     '26-DAP'
_chemical_formula_moiety     'C5 H7 N3'
_chemical_formula_sum     'C5 H7 N3'
_chemical_formula_iupac     'C5 H7 N3'
_chemical_formula_weight     109.14
_chemical_melting_point     ?
_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.
;
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P b c a'
_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    '-x-1/2, y-1/2, z'
    'x, -y-1/2, z-1/2'
_cell_length_a     5.1217(9)
_cell_length_b     9.8397(14)
_cell_length_c     21.914(4)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1104.4(3)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     10034
_cell_measurement_theta_min     3.71
_cell_measurement_theta_max     19.59
_cell_measurement_temperature     100(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.440
_exptl_crystal_size_mid     0.048
_exptl_crystal_size_min     0.023
_exptl_crystal_density_diffrn     1.313
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     464
_exptl_absorpt_coefficient_mu     0.087
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_shelx_estimated_absorpt_T_min     0.963
_shelx_estimated_absorpt_T_max     0.998
_exptl_absorpt_correction_T_min     0.5181
_exptl_absorpt_correction_T_max     0.7451
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     'multilayer mirrors'
_diffrn_measurement_device     'Bruker APEX DUO/APEXII CCD'
_diffrn_measurement_method     'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8750
_diffrn_reflns_av_R_equivalents     0.1798
_diffrn_reflns_theta_min     1.859
_diffrn_reflns_theta_max     24.893
_diffrn_reflns_theta_full     24.893
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -25
_diffrn_reflns_limit_l_max     25
_refine_special_details     ?
_reflns_number_total     948
_reflns_number_gt     559
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1189
_refine_ls_R_factor_gt     0.0561
_refine_ls_wR_factor_gt     0.1204
_refine_ls_wR_factor_ref     0.1490
_refine_ls_goodness_of_fit_ref     0.984
_refine_ls_restrained_S_all     0.983
_refine_ls_number_reflns     948
_refine_ls_number_parameters     86
_refine_ls_number_restraints     4
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0763P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.320
_refine_diff_density_min     -0.236
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015b)
;
_refine_ls_extinction_coef     0.018(4)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014), XPREP (Bruker, 2014) and SADABS (Bruker,
2014)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
SHELXTL (Bruker, 2014)
;
_computing_publication_material
;
XCIF (Bruker, 2014)
;
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.0267(5) 0.6215(2) 0.18272(11) 0.0207(7) Uani d 1 . .
    N N2 -0.3151(5) 0.4730(3) 0.17132(13) 0.0272(8) Uani d 1 . .
    H H2A -0.460(5) 0.456(4) 0.1506(14) 0.041 Uiso d 1 . .
    H H2B -0.343(7) 0.487(4) 0.2108(9) 0.041 Uiso d 1 . .
    N N3 0.3660(6) 0.7692(3) 0.20060(12) 0.0237(7) Uani d 1 . .
    H H3A 0.399(7) 0.730(3) 0.2371(10) 0.036 Uiso d 1 . .
    H H3B 0.511(5) 0.806(3) 0.1854(15) 0.036 Uiso d 1 . .
    C C1 -0.1445(6) 0.5638(3) 0.14421(14) 0.0231(8) Uani d 1 . .
    C C2 -0.1450(7) 0.5874(3) 0.08154(14) 0.0298(9) Uani d 1 . .
    H H2 -0.2679 0.5442 0.0555 0.036 Uiso calc 1 . .
    C C3 0.0409(7) 0.6765(4) 0.05851(16) 0.0333(10) Uani d 1 . .
    H H3 0.0474 0.6948 0.0160 0.040 Uiso calc 1 . .
    C C4 0.2160(6) 0.7385(3) 0.09735(14) 0.0257(8) Uani d 1 . .
    H H4 0.3418 0.8007 0.0820 0.031 Uiso calc 1 . .
    C C5 0.2056(6) 0.7086(3) 0.15879(13) 0.0201(8) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    N1 C1 . 1.343(4) ?
    N1 C5 . 1.360(4) ?
    N2 C1 . 1.384(4) ?
    N2 H2A . 0.886(18) ?
    N2 H2B . 0.888(18) ?
    N3 C5 . 1.368(4) ?
    N3 H3A . 0.902(18) ?
    N3 H3B . 0.891(18) ?
    C1 C2 . 1.393(4) ?
    C2 C3 . 1.389(5) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.378(5) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.379(4) ?
    C4 H4 . 0.9500 ?
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
    C1 N1 C5 . . 117.6(3) ?
    C1 N2 H2A . . 115(2) ?
    C1 N2 H2B . . 115(2) ?
    H2A N2 H2B . . 113(3) ?
    C5 N3 H3A . . 121(2) ?
    C5 N3 H3B . . 115(2) ?
    H3A N3 H3B . . 110(3) ?
    N1 C1 N2 . . 114.5(3) ?
    N1 C1 C2 . . 123.4(3) ?
    N2 C1 C2 . . 122.0(3) ?
    C3 C2 C1 . . 117.5(3) ?
    C3 C2 H2 . . 121.2 ?
    C1 C2 H2 . . 121.2 ?
    C4 C3 C2 . . 120.0(3) ?
    C4 C3 H3 . . 120.0 ?
    C2 C3 H3 . . 120.0 ?
    C3 C4 C5 . . 118.9(3) ?
    C3 C4 H4 . . 120.5 ?
    C5 C4 H4 . . 120.5 ?
    N1 C5 N3 . . 114.9(3) ?
    N1 C5 C4 . . 122.5(3) ?
    N3 C5 C4 . . 122.6(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
    C5 N1 C1 N2 . . . . 178.0(3) ?
    C5 N1 C1 C2 . . . . 0.9(4) ?
    N1 C1 C2 C3 . . . . -0.7(5) ?
    N2 C1 C2 C3 . . . . -177.5(3) ?
    C1 C2 C3 C4 . . . . -0.4(5) ?
    C2 C3 C4 C5 . . . . 1.1(5) ?
    C1 N1 C5 N3 . . . . 176.9(3) ?
    C1 N1 C5 C4 . . . . -0.2(4) ?
    C3 C4 C5 N1 . . . . -0.8(5) ?
    C3 C4 C5 N3 . . . . -177.7(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
    N3 H3A N1 6_656 0.902(18) 2.16(2) 3.054(4) 171(3)
    N3 H3B N2 7_665 0.891(18) 2.29(2) 3.118(4) 155(3)
