#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/55/2215599.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_2215599
loop_
_publ_author_name
'Wang, Pin-liang'
'Li, Hai-ling'
'Zeng, Hai-su'
'Kang, Si-shun'
'Wang, Hai-bo'
_publ_section_title
;
 N'-Hydroxynicotinamidine
;
_journal_coeditor_code           LW2034
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4151
_journal_page_last               o4151
_journal_paper_doi               10.1107/S1600536807046508
_journal_volume                  63
_journal_year                    2007
_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
;
N'-Hydroxynicotinamidine
;
_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'
_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                 94.38(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5220(11)
_cell_length_b                   12.365(3)
_cell_length_c                   9.797(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     667.0(3)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo,1995)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1996)'
_computing_publication_material  'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0548
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1444
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         2.66
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9702
_exptl_absorpt_correction_T_min  0.9505
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1307
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0595
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0466P)²+0.3602P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1577
_reflns_number_gt                782
_reflns_number_total             1307
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lw2034.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     '-p 2ybc'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2215599
_cod_database_fobs_code          2215599
loop_
_symmetry_equiv_pos_as_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
O O1 0.6266(4) 0.85703(19) 0.2247(2) 0.0575(7) Uani d . 1
H H1A 0.6800 0.8630 0.1492 0.086 Uiso calc R 1
N N1 -0.1856(5) 0.6347(2) 0.4713(3) 0.0523(7) Uani d . 1
N N2 0.4172(5) 0.8367(2) 0.4451(3) 0.0538(8) Uani d . 1
H H2A 0.5697 0.8776 0.4355 0.072(11) Uiso d R 1
H H2B 0.4664 0.8136 0.5387 0.111(16) Uiso d R 1
N N3 0.4391(5) 0.7778(2) 0.2184(3) 0.0466(7) Uani d . 1
C C1 -0.2182(6) 0.5548(3) 0.3844(4) 0.0564(9) Uani d . 1
H H1B -0.3460 0.5073 0.3953 0.068 Uiso calc R 1
C C2 -0.0749(6) 0.5366(3) 0.2776(4) 0.0568(9) Uani d . 1
H H2C -0.1067 0.4794 0.2172 0.068 Uiso calc R 1
C C3 0.1172(6) 0.6057(3) 0.2633(3) 0.0501(9) Uani d . 1
H H3B 0.2206 0.5942 0.1941 0.060 Uiso calc R 1
C C4 0.1560(6) 0.6916(2) 0.3512(3) 0.0424(8) Uani d . 1
C C5 0.0006(6) 0.7027(3) 0.4547(3) 0.0468(8) Uani d . 1
H H5A 0.0259 0.7599 0.5158 0.056 Uiso calc R 1
C C6 0.3564(5) 0.7710(2) 0.3388(3) 0.0406(7) Uani d . 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
O1 0.0685(16) 0.0605(15) 0.0481(13) -0.0083(13) 0.0346(11) 0.0048(12)
N1 0.0523(17) 0.0572(17) 0.0510(16) 0.0048(15) 0.0278(13) 0.0007(15)
N2 0.071(2) 0.0523(17) 0.0416(16) -0.0005(15) 0.0278(14) 0.0007(14)
N3 0.0516(16) 0.0485(16) 0.0433(15) 0.0003(13) 0.0275(12) 0.0037(12)
C1 0.055(2) 0.058(2) 0.059(2) -0.0029(18) 0.0205(18) 0.0033(18)
C2 0.073(2) 0.0444(19) 0.056(2) -0.0005(19) 0.0236(18) -0.0053(17)
C3 0.062(2) 0.052(2) 0.0397(17) 0.0036(18) 0.0284(16) 0.0020(15)
C4 0.0523(19) 0.0395(17) 0.0384(16) 0.0085(15) 0.0235(14) 0.0056(13)
C5 0.0506(18) 0.0514(19) 0.0417(17) 0.0002(17) 0.0247(15) -0.0041(15)
C6 0.0460(18) 0.0427(18) 0.0355(16) 0.0118(14) 0.0194(13) 0.0068(14)
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'
O O 0.0106 0.0060 '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
N3 O1 H1A 109.5
C1 N1 C5 117.5(3)
C6 N2 H2A 113.5
C6 N2 H2B 125.8
H2A N2 H2B 93.5
C6 N3 O1 108.1(2)
N1 C1 C2 124.0(3)
N1 C1 H1B 118.0
C2 C1 H1B 118.0
C3 C2 C1 117.9(3)
C3 C2 H2C 121.1
C1 C2 H2C 121.1
C4 C3 C2 120.0(3)
C4 C3 H3B 120.0
C2 C3 H3B 120.0
C3 C4 C5 117.4(3)
C3 C4 C6 122.6(3)
C5 C4 C6 119.9(3)
N1 C5 C4 123.2(3)
N1 C5 H5A 118.4
C4 C5 H5A 118.4
N3 C6 N2 125.5(3)
N3 C6 C4 115.5(3)
N2 C6 C4 118.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N3 1.423(3)
O1 H1A 0.8200
N1 C1 1.308(4)
N1 C5 1.348(4)
N2 C6 1.343(4)
N2 H2A 0.9929
N2 H2B 0.9787
N3 C6 1.300(4)
C1 C2 1.378(4)
C1 H1B 0.9300
C2 C3 1.378(4)
C2 H2C 0.9300
C3 C4 1.373(4)
C3 H3B 0.9300
C4 C5 1.385(4)
C4 C6 1.491(4)
C5 H5A 0.9300
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 N3 4_576 0.98 2.11 3.023(4) 155
O1 H1A N1 4_675 0.82 1.95 2.767(4) 176
N2 H2A O1 . 0.99 2.13 2.539(4) 103
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 C2 -0.2(5)
N1 C1 C2 C3 1.3(5)
C1 C2 C3 C4 -2.1(5)
C2 C3 C4 C5 1.9(5)
C2 C3 C4 C6 -178.3(3)
C1 N1 C5 C4 0.0(5)
C3 C4 C5 N1 -0.9(5)
C6 C4 C5 N1 179.3(3)
O1 N3 C6 N2 7.4(4)
O1 N3 C6 C4 179.7(2)
C3 C4 C6 N3 22.5(4)
C5 C4 C6 N3 -157.7(3)
C3 C4 C6 N2 -164.7(3)
C5 C4 C6 N2 15.1(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 272373
2 PubChem 5372334
