#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/57/2235797.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_2235797
loop_
_publ_author_name
'Ntsala, Lerato P.'
'Lemmerer, Andreas'
_publ_section_title
;
 6-Aminonicotinamide
;
_journal_coeditor_code           FJ2584
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2449
_journal_paper_doi               10.1107/S1600536812031224
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C6 H7 N3 O'
_chemical_formula_moiety         'C6 H7 N3 O'
_chemical_formula_sum            'C6 H7 N3 O'
_chemical_formula_weight         137.15
_chemical_name_systematic
;
6-Aminonicotinamide
;
_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'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 99.215(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3483(6)
_cell_length_b                   4.8143(2)
_cell_length_c                   9.6685(4)
_cell_measurement_reflns_used    1574
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.42
_cell_measurement_theta_min      2.88
_cell_volume                     659.25(5)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4078
_diffrn_reflns_theta_full        28
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_min         2.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.1
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.9735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     107
_refine_ls_number_reflns         1582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0577P)²+0.1618P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1133
_reflns_number_gt                1300
_reflns_number_total             1582
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fj2584.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2235797
_cod_database_fobs_code          2235797
loop_
_space_group_symop_operation_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
C C1 0.21465(8) 0.3830(3) 0.06966(12) 0.0216(3) Uani d . 1
C C2 0.28897(8) 0.3112(3) 0.00180(12) 0.0227(3) Uani d . 1
H H2 0.279 0.1654 -0.0651 0.027 Uiso calc R 1
C C3 0.38732(8) 0.6424(2) 0.11660(12) 0.0212(3) Uani d . 1
C C4 0.31587(9) 0.7304(3) 0.19125(13) 0.0246(3) Uani d . 1
H H4 0.3271 0.878 0.257 0.03 Uiso calc R 1
C C5 0.22979(9) 0.5994(3) 0.16746(13) 0.0242(3) Uani d . 1
H H5 0.1808 0.6552 0.217 0.029 Uiso calc R 1
C C6 0.12477(8) 0.2249(3) 0.03728(12) 0.0235(3) Uani d . 1
N N1 0.06896(8) 0.2202(3) 0.13454(12) 0.0315(3) Uani d . 1
H H1S 0.0150(13) 0.121(3) 0.1119(18) 0.037(4) Uiso d . 1
H H1A 0.0869(12) 0.292(3) 0.219(2) 0.036(4) Uiso d . 1
N N2 0.37410(7) 0.4326(2) 0.02370(11) 0.0232(3) Uani d . 1
N N3 0.47474(8) 0.7598(2) 0.14074(13) 0.0275(3) Uani d . 1
H H3S 0.5162(12) 0.710(4) 0.0824(19) 0.037(4) Uiso d . 1
H H3A 0.4816(12) 0.918(3) 0.1855(18) 0.034(4) Uiso d . 1
O O1 0.10436(6) 0.0996(2) -0.07631(9) 0.0295(3) Uani 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 0 '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 0.006 '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
C2 C1 C5 117.29(11)
C2 C1 C6 118.75(11)
C5 C1 C6 123.95(11)
N2 C2 C1 124.66(11)
N2 C2 H2 117.7
C1 C2 H2 117.7
N2 C3 N3 116.99(11)
N2 C3 C4 122.08(11)
N3 C3 C4 120.87(11)
C5 C4 C3 118.99(11)
C5 C4 H4 120.5
C3 C4 H4 120.5
C4 C5 C1 119.53(11)
C4 C5 H5 120.2
C1 C5 H5 120.2
O1 C6 N1 122.15(12)
O1 C6 C1 120.45(11)
N1 C6 C1 117.39(11)
C6 N1 H1S 115.2(11)
C6 N1 H1A 121.9(11)
H1S N1 H1A 122.5(16)
C2 N2 C3 117.43(10)
C3 N3 H3S 117.2(11)
C3 N3 H3A 118.4(11)
H3S N3 H3A 120.1(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3824(17)
C1 C5 1.4004(17)
C1 C6 1.4870(16)
C2 N2 1.3401(15)
C2 H2 0.95
C3 N2 1.3449(15)
C3 N3 1.3614(15)
C3 C4 1.4100(17)
C4 C5 1.3730(17)
C4 H4 0.95
C5 H5 0.95
C6 O1 1.2461(15)
C6 N1 1.3293(16)
N1 H1S 0.907(18)
N1 H1A 0.888(18)
N3 H3S 0.915(18)
N3 H3A 0.875(17)
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 H1A O1 4_566 0.888(18) 2.021(19) 2.8933(15) 167.2(15)
N1 H1S O1 3 0.907(18) 1.997(19) 2.9024(14) 176.0(16)
N3 H3S N2 3_665 0.915(18) 2.125(19) 3.0322(15) 170.9(15)
N3 H3A N3 2_655 0.875(17) 2.363(17) 3.2083(16) 162.7(15)
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 C1 C2 N2 0.43(19)
C6 C1 C2 N2 -178.45(11)
N2 C3 C4 C5 -0.61(19)
N3 C3 C4 C5 -177.58(11)
C3 C4 C5 C1 -0.24(18)
C2 C1 C5 C4 0.34(18)
C6 C1 C5 C4 179.15(11)
C2 C1 C6 O1 -23.55(18)
C5 C1 C6 O1 157.66(12)
C2 C1 C6 N1 155.44(12)
C5 C1 C6 N1 -23.36(18)
C1 C2 N2 C3 -1.24(18)
N3 C3 N2 C2 178.40(11)
C4 C3 N2 C2 1.31(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 9500
