#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/24/2212451.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_2212451
loop_
_publ_author_name
'Golenya, Irina A.'
'Haukka, Matti'
'Fritsky, Igor O.'
'Gumienna-Kontecka, Elźbieta'
_publ_section_title
;
 4-(Hydroxyaminocarbonyl)pyridinium chloride
;
_journal_coeditor_code           BH2082
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1515
_journal_page_last               o1517
_journal_paper_doi               10.1107/S1600536807008604
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C6 H7 N2 O2 + , Cl -'
_chemical_formula_moiety         'C6 H7 N2 O2 + , Cl -'
_chemical_formula_sum            'C6 H7 Cl N2 O2'
_chemical_formula_weight         174.59
_chemical_name_common
;
N-Hydroxyisonicotinamidium chloride
;
_chemical_name_systematic
;
4-(Hydroxyaminocarbonyl)pyridinium chloride
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.0421(2)
_cell_length_b                   14.3771(3)
_cell_length_c                   14.7134(4)
_cell_measurement_reflns_used    6083
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1489.66(7)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Bruker, 2004)'
_computing_data_reduction
'SCALEPACK and DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ scans, and ω scans with κ offset'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24587
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.77
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.459
_exptl_absorpt_correction_T_max  0.9624
_exptl_absorpt_correction_T_min  0.8806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.256
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1713
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0304
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0347P)²+0.8006P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0795
_reflns_number_gt                1441
_reflns_number_total             1713
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2082.cif
_cod_data_source_block           I
_cod_database_code               2212451
_cod_database_fobs_code          2212451
loop_
_symmetry_equiv_pos_as_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'
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
Cl Cl1 0.40487(5) 0.26771(2) 0.91981(2) 0.02139(13) Uani d 1
O O1 0.70115(17) 0.05181(7) 0.66663(7) 0.0232(3) Uani d 1
O O2 0.54033(17) 0.22468(8) 0.67394(7) 0.0237(3) Uani d 1
N N1 0.72875(18) -0.06610(9) 0.98268(8) 0.0179(3) Uani d 1
N N2 0.58811(19) 0.17246(8) 0.75041(9) 0.0190(3) Uani d 1
C C1 0.6583(2) 0.08725(10) 0.74018(10) 0.0164(3) Uani d 1
C C2 0.6843(2) 0.03478(10) 0.82768(9) 0.0154(3) Uani d 1
C C3 0.7343(2) 0.07867(10) 0.90854(10) 0.0172(3) Uani d 1
C C4 0.7566(2) 0.02625(10) 0.98621(10) 0.0177(3) Uani d 1
C C5 0.6824(2) -0.11095(10) 0.90599(10) 0.0202(3) Uani d 1
C C6 0.6605(2) -0.06168(10) 0.82644(10) 0.0192(3) Uani d 1
H H3 0.757(3) 0.1439(14) 0.9109(11) 0.029(5) Uiso d 1
H H4 0.791(2) 0.0543(12) 1.0454(12) 0.023(4) Uiso d 1
H H5 0.664(3) -0.1761(15) 0.9118(12) 0.032(5) Uiso d 1
H H6 0.629(3) -0.0915(13) 0.7737(12) 0.024(4) Uiso d 1
H H1N 0.739(3) -0.0994(15) 1.0339(14) 0.041(6) Uiso d 1
H H2N 0.545(3) 0.1961(14) 0.8043(13) 0.030(5) Uiso d 1
H H2O 0.654(3) 0.2384(14) 0.6487(14) 0.036(6) Uiso 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
Cl1 0.0228(2) 0.0204(2) 0.0210(2) 0.00073(14) 0.00090(15) -0.00580(14)
O1 0.0329(6) 0.0232(5) 0.0134(5) 0.0012(5) 0.0028(5) -0.0020(4)
O2 0.0228(6) 0.0283(6) 0.0200(6) 0.0038(5) -0.0003(5) 0.0119(5)
N1 0.0202(7) 0.0182(6) 0.0151(6) 0.0023(5) -0.0009(5) 0.0032(5)
N2 0.0235(7) 0.0198(6) 0.0136(6) 0.0037(5) 0.0004(5) 0.0040(5)
C1 0.0152(7) 0.0193(7) 0.0148(7) -0.0020(6) 0.0001(6) 0.0003(6)
C2 0.0135(7) 0.0184(7) 0.0142(7) 0.0015(5) 0.0010(6) 0.0005(5)
C3 0.0193(7) 0.0147(7) 0.0176(7) -0.0011(6) -0.0008(6) -0.0007(5)
C4 0.0195(7) 0.0172(7) 0.0163(7) 0.0006(6) -0.0015(6) -0.0016(6)
C5 0.0241(8) 0.0142(7) 0.0224(8) -0.0002(6) -0.0018(6) -0.0004(6)
C6 0.0220(8) 0.0191(7) 0.0166(7) 0.0005(6) -0.0022(6) -0.0044(6)
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
N2 O2 H2O 103.7(13) no
C5 N1 C4 122.94(13) yes
C5 N1 H1N 118.0(13) no
C4 N1 H1N 119.0(13) no
C1 N2 O2 119.65(12) yes
C1 N2 H2N 124.4(12) no
O2 N2 H2N 114.7(12) no
O1 C1 N2 124.80(13) yes
O1 C1 C2 120.95(13) yes
N2 C1 C2 114.24(12) yes
C3 C2 C6 119.44(13) yes
C3 C2 C1 122.36(13) yes
C6 C2 C1 118.19(13) yes
C4 C3 C2 119.33(13) yes
C4 C3 H3 119.3(10) no
C2 C3 H3 121.4(10) no
N1 C4 C3 119.47(13) yes
N1 C4 H4 118.2(10) no
C3 C4 H4 122.3(10) no
N1 C5 C6 119.71(13) yes
N1 C5 H5 115.6(11) no
C6 C5 H5 124.7(11) no
C5 C6 C2 119.09(14) yes
C5 C6 H6 120.6(11) no
C2 C6 H6 120.3(11) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.2336(17) yes
O2 N2 1.3938(16) yes
O2 H2O 0.90(2) no
N1 C5 1.3400(19) yes
N1 C4 1.3431(19) yes
N1 H1N 0.90(2) no
N2 C1 1.3296(19) yes
N2 H2N 0.916(19) no
C1 C2 1.5033(19) yes
C2 C3 1.392(2) yes
C2 C6 1.397(2) yes
C3 C4 1.378(2) yes
C3 H3 0.95(2) no
C4 H4 0.990(18) no
C5 C6 1.377(2) yes
C5 H5 0.95(2) no
C6 H6 0.914(18) no
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
_geom_hbond_publ_flag
N1 H1N O1 2_655 0.90(2) 2.11(2) 2.7588(16) 128.3(18) yes
N1 H1N Cl1 5_657 0.90(2) 2.71(2) 3.3683(13) 131.3(17) yes
N2 H2N Cl1 . 0.916(19) 2.22(2) 3.1230(14) 170.0(17) yes
O2 H2O Cl1 6_657 0.90(2) 2.08(2) 2.9792(13) 175.3(19) yes
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
_geom_torsion_publ_flag
O2 N2 C1 O1 6.5(2) no
O2 N2 C1 C2 -173.80(12) no
O1 C1 C2 C3 145.92(15) no
N2 C1 C2 C3 -33.8(2) no
O1 C1 C2 C6 -32.8(2) no
N2 C1 C2 C6 147.46(14) no
C6 C2 C3 C4 -1.0(2) no
C1 C2 C3 C4 -179.69(13) no
C5 N1 C4 C3 1.1(2) no
C2 C3 C4 N1 -0.4(2) no
C4 N1 C5 C6 -0.4(2) no
N1 C5 C6 C2 -1.0(2) no
C3 C2 C6 C5 1.6(2) no
C1 C2 C6 C5 -179.59(14) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21125284
