#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/19/2201925.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_2201925
loop_
_publ_author_name
'Koman, Marian'
'Martiška, Ladislav'
'Valigura, Dušan'
'Glowiak, Tadeuš'
_publ_section_title
;
 1H-Nicotinamidium 3,5-dinitrosalicylate
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o441
_journal_page_last               o442
_journal_paper_doi               10.1107/S1600536803005166
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C6 H7 N2 O1 1+, C7 H3 N2 O7 1-'
_chemical_formula_moiety         'C6 H7 N2 O1 1+, C7 H3 N2 O7 1-'
_chemical_formula_sum            'C13 H10 N4 O8'
_chemical_formula_weight         350.25
_chemical_melting_point          458
_chemical_name_common            '1H-nicotinamidium 3,5-dinitrosalicylate'
_chemical_name_systematic        '1H-nicotinamidium 3,5-dinitrosalicylate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-93
_cell_angle_alpha                90.00
_cell_angle_beta                 94.62(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.7400(10)
_cell_length_b                   21.968(4)
_cell_length_c                   13.858(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11.8
_cell_measurement_theta_min      4.5
_cell_volume                     1438.3(5)
_computing_cell_refinement       'Syntax P2₁ Software'
_computing_data_collection       'Syntax P2₁ Software (Syntex, 1974)'
_computing_data_reduction        'XP21 (Pavelčík, 1993)'
_computing_molecular_graphics    'ORTEP (Johnson, 1965)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1994)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.898
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_device_type  'Syntex P2₁'
_diffrn_measurement_method       θ-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_av_sigmaI/netI    0.107
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3511
_diffrn_reflns_theta_full        65.07
_diffrn_reflns_theta_max         65.1
_diffrn_reflns_theta_min         3.80
_diffrn_standards_decay_%        15
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    1.20
_exptl_absorpt_correction_T_max  0.741
_exptl_absorpt_correction_T_min  0.544
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0399
_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)+(0.0618P)²+0.1656P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1099
_reflns_number_gt                1631
_reflns_number_total             2212
_reflns_threshold_expression     I>2Ĭ)
_cod_data_source_file            cv6166.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2201925
_cod_database_fobs_code          2201925
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.1009(3) 0.61448(7) 0.90611(10) 0.0531(4) Uani d . 1 . . O
O2 0.0081(4) 0.67232(7) 0.77654(11) 0.0593(5) Uani d . 1 . . O
O3 0.2416(5) 0.65338(10) 0.62978(14) 0.0598(8) Uani d P 0.756(5) . . O
O3' 0.4525(12) 0.5346(3) 0.9078(4) 0.049(2) Uiso d P 0.244(5) . . O
O4 0.4483(6) 0.61849(12) 0.47593(14) 0.0961(8) Uani d . 1 . . O
O5 0.7735(6) 0.55335(13) 0.48105(16) 0.1091(9) Uani d . 1 . . O
O6 1.0494(4) 0.44392(8) 0.76707(17) 0.0766(6) Uani d . 1 . . O
O7 0.8103(5) 0.44969(9) 0.89099(14) 0.0822(6) Uani d . 1 . . O
O8 -0.4078(3) 0.80338(7) 0.72734(10) 0.0483(4) Uani d . 1 . . O
N1 0.5982(5) 0.58166(9) 0.51934(13) 0.0545(5) Uani d . 1 . . N
N2 0.8625(4) 0.46639(8) 0.81108(15) 0.0527(5) Uani d . 1 . . N
N3 0.0148(4) 0.84673(9) 0.76834(12) 0.0486(5) Uani d . 1 . . N
N4 0.2075(4) 0.82145(8) 0.48136(11) 0.0417(4) Uani d . 1 . . N
C1 0.3446(4) 0.59331(8) 0.76774(13) 0.0374(4) Uani d . 1 . . C
C2 0.3772(4) 0.60750(8) 0.67004(13) 0.0401(4) Uani d . 1 . . C
C3 0.5656(5) 0.57173(9) 0.62151(14) 0.0421(5) Uani d . 1 . . C
C4 0.7235(5) 0.52589(9) 0.66740(15) 0.0440(5) Uani d . 1 . . C
C5 0.6888(4) 0.51422(8) 0.76299(15) 0.0409(5) Uani d . 1 . . C
C6 0.4990(4) 0.54693(8) 0.81421(13) 0.0396(4) Uani d . 1 . . C
C7 0.1375(5) 0.62926(9) 0.82058(14) 0.0429(5) Uani d . 1 . . C
C8 -0.0685(4) 0.80166(8) 0.61132(13) 0.0349(4) Uani d . 1 . . C
C9 0.1295(4) 0.83650(8) 0.56883(13) 0.0378(4) Uani d . 1 . . C
C10 0.1022(5) 0.77346(10) 0.43197(14) 0.0487(5) Uani d . 1 . . C
C11 -0.0966(5) 0.73825(10) 0.47096(16) 0.0551(6) Uani d . 1 . . C
C12 -0.1842(5) 0.75225(9) 0.56066(15) 0.0445(5) Uani d . 1 . . C
C13 -0.1675(4) 0.81733(9) 0.70847(13) 0.0372(4) Uani d . 1 . . C
H3 0.1131 0.6712 0.7090 0.050 Uiso d P 0.76 . . H
H3' 0.2913 0.5630 0.9303 0.050 Uiso d P 0.24 . . H
H4 0.8527 0.5034 0.6347 0.050 Uiso d . 1 . . H
H6 0.4753 0.5377 0.8786 0.050 Uiso d . 1 . . H
H9 0.2072 0.8702 0.6011 0.050 Uiso d . 1 . . H
H10 0.1642 0.7639 0.3716 0.050 Uiso d . 1 . . H
H11 -0.1711 0.7047 0.4365 0.050 Uiso d . 1 . . H
H12 -0.3232 0.7291 0.5869 0.050 Uiso d . 1 . . H
H31 -0.0332 0.8576 0.8245 0.050 Uiso d . 1 . . H
H32 0.1790 0.8558 0.7509 0.050 Uiso d . 1 . . H
H41 0.3310 0.8441 0.4561 0.050 Uiso d . 1 . . H
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 0.0311 0.0180 '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
_geom_angle_publ_flag
C7 O1 H3' 106.6 ?
C7 O2 H3 99.2 ?
C2 O3 H3 96.6 ?
C6 O3' H3' 109.9 ?
C6 O3' H6 5.5 ?
H3' O3' H6 115.0 ?
O5 N1 O4 122.0(2) y
O5 N1 C3 119.1(2) y
O4 N1 C3 118.8(2) y
O7 N2 O6 123.0(2) y
O7 N2 C5 119.1(2) y
O6 N2 C5 117.9(2) y
C13 N3 H31 119.8 ?
C13 N3 H32 120.1 ?
H31 N3 H32 120.1 ?
C9 N4 C10 122.82(17) y
C9 N4 H41 118.1 ?
C10 N4 H41 119.1 ?
C6 C1 C2 121.02(18) y
C6 C1 C7 120.29(17) y
C2 C1 C7 118.68(18) y
O3 C2 C3 122.82(18) y
O3 C2 C1 119.74(19) y
C3 C2 C1 117.40(18) y
C4 C3 C2 122.08(17) y
C4 C3 N1 117.56(19) y
C2 C3 N1 120.35(19) y
C5 C4 C3 118.61(18) y
C5 C4 H4 120.3 ?
C3 C4 H4 121.0 ?
C4 C5 C6 121.96(19) y
C4 C5 N2 117.87(18) y
C6 C5 N2 120.16(18) y
O3' C6 C1 118.1(3) ?
O3' C6 C5 123.0(3) ?
C1 C6 C5 118.88(17) ?
O3' C6 H6 2.6 ?
C1 C6 H6 120.5 ?
C5 C6 H6 120.7 ?
O1 C7 O2 123.63(18) y
O1 C7 C1 118.15(19) y
O2 C7 C1 118.22(17) y
C9 C8 C12 118.35(17) y
C9 C8 C13 121.89(17) y
C12 C8 C13 119.73(17) y
N4 C9 C8 119.81(18) y
N4 C9 H9 120.5 ?
C8 C9 H9 119.7 ?
N4 C10 C11 119.19(18) y
N4 C10 H10 120.5 ?
C11 C10 H10 120.3 ?
C10 C11 C12 119.95(19) y
C10 C11 H11 119.4 ?
C12 C11 H11 120.7 ?
C8 C12 C11 119.87(19) y
C8 C12 H12 119.7 ?
C11 C12 H12 120.4 ?
O8 C13 N3 124.10(18) y
O8 C13 C8 119.74(18) y
N3 C13 C8 116.15(17) y
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
O1 C7 . 1.254(2) y
O2 C7 . 1.258(3) y
O3 C2 . 1.297(3) y
O4 N1 . 1.205(3) y
O5 N1 . 1.196(3) y
O6 N2 . 1.220(3) y
O7 N2 . 1.211(3) y
O8 C13 . 1.228(2) y
N1 C3 . 1.453(3) y
N2 C5 . 1.462(3) y
N3 C13 . 1.318(3) y
N3 H31 . 0.8622 ?
N3 H32 . 0.8565 ?
N4 C9 . 1.337(3) y
N4 C10 . 1.332(3) y
N4 H41 . 0.8637 ?
C1 C6 . 1.383(3) y
C1 C2 . 1.410(3) y
C1 C7 . 1.497(3) y
C2 C3 . 1.402(3) y
C3 C4 . 1.379(3) y
C4 C5 . 1.372(3) y
C4 H4 . 0.9317 ?
C5 C6 . 1.390(3) y
C6 H6 . 0.9302 ?
C8 C9 . 1.379(3) y
C8 C12 . 1.382(3) y
C8 C13 . 1.501(2) y
C9 H9 . 0.9256 ?
C10 C11 . 1.364(3) y
C10 H10 . 0.9324 ?
C11 C12 . 1.377(3) y
C11 H11 . 0.9317 ?
C12 H12 . 0.9299 ?
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 H31 O4 4_576 0.86 2.17 3.018(2) 167
N3 H32 O8 1_655 0.86 2.32 2.995(2) 136
N3 H32 O6 2_656 0.86 2.35 3.038(3) 138
N4 H41 O1 4_675 0.86 1.76 2.619(2) 176
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
C6 C1 C2 O3 -176.2(2)
C7 C1 C2 O3 4.2(3)
C6 C1 C2 C3 1.7(3)
C7 C1 C2 C3 -177.91(18)
O3 C2 C3 C4 175.2(2)
C1 C2 C3 C4 -2.6(3)
O3 C2 C3 N1 -5.5(3)
C1 C2 C3 N1 176.67(18)
O5 N1 C3 C4 -5.6(3)
O4 N1 C3 C4 174.8(2)
O5 N1 C3 C2 175.1(2)
O4 N1 C3 C2 -4.5(3)
C2 C3 C4 C5 1.6(3)
N1 C3 C4 C5 -177.70(18)
C3 C4 C5 C6 0.4(3)
C3 C4 C5 N2 -178.65(17)
O7 N2 C5 C4 -170.3(2)
O6 N2 C5 C4 7.7(3)
O7 N2 C5 C6 10.7(3)
O6 N2 C5 C6 -171.4(2)
C2 C1 C6 O3' -178.4(3)
C7 C1 C6 O3' 1.2(4)
C2 C1 C6 C5 0.1(3)
C7 C1 C6 C5 179.73(18)
C4 C5 C6 O3' 177.2(3)
N2 C5 C6 O3' -3.8(4)
C4 C5 C6 C1 -1.2(3)
N2 C5 C6 C1 177.80(18)
C6 C1 C7 O1 -2.8(3)
C2 C1 C7 O1 176.84(19)
C6 C1 C7 O2 177.76(19)
C2 C1 C7 O2 -2.6(3)
C10 N4 C9 C8 -0.1(3)
C12 C8 C9 N4 -1.0(3)
C13 C8 C9 N4 -178.76(17)
C9 N4 C10 C11 0.9(3)
N4 C10 C11 C12 -0.5(3)
C9 C8 C12 C11 1.3(3)
C13 C8 C12 C11 179.13(19)
C10 C11 C12 C8 -0.6(3)
C9 C8 C13 O8 150.58(19)
C12 C8 C13 O8 -27.2(3)
C9 C8 C13 N3 -28.4(3)
C12 C8 C13 N3 153.80(19)
