#------------------------------------------------------------------------------
#$Date: 2025-08-19 14:52:15 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301804 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/72/2217227.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_2217227
loop_
_publ_author_name
'Abbasi, Alireza'
'Badiei, Alireza'
'Tarighi, Sara'
_publ_section_title
;
 5,6-Dioxo-1,10-phenanthrolin-1-ium nitrate
;
_journal_coeditor_code           NG2405
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o290
_journal_page_last               o290
_journal_paper_doi               10.1107/S1600536807066172
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C12 H7 N2 O2 + , N O3 -'
_chemical_formula_moiety         'C12 H7 N2 O2 + , N O3 -'
_chemical_formula_sum            'C12 H7 N3 O5'
_chemical_formula_weight         273.21
_chemical_name_systematic
;
5,6-Dioxo-1,10-phenanthrolin-1-ium nitrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.720(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.4860(19)
_cell_length_b                   12.5177(13)
_cell_length_c                   13.4535(16)
_cell_measurement_reflns_used    7311
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.5
_cell_volume                     2388.7(5)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2003)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2003)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2003)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2001)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 12
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur 3 CCD'
_diffrn_measurement_method       'ω-scans at different φ'
_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  0.0684
_diffrn_reflns_av_sigmaI/netI    0.1645
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7311
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.77
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.9601
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(X-RED; Stoe & Cie, 1997)'
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.141
_refine_ls_extinction_coef       0.00072(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   0.827
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2095
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.827
_refine_ls_R_factor_all          0.1450
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.01P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0549
_refine_ls_wR_factor_ref         0.0602
_reflns_number_gt                635
_reflns_number_total             2095
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2405.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2217227
_cod_database_fobs_code          2217227
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.85417(17) -0.13522(19) 0.12439(18) 0.0673(8) Uani d . 1
O O2 0.85003(19) 0.08376(19) 0.1238(2) 0.0834(10) Uani d . 1
O O3 0.30299(14) 0.0377(2) 0.07097(16) 0.0649(7) Uani d . 1
O O4 0.22236(15) -0.03456(19) 0.17219(15) 0.0613(6) Uani d . 1
O O5 0.34903(16) -0.11186(18) 0.14632(16) 0.0622(7) Uani d . 1
N N1 0.52797(19) -0.1426(2) 0.12265(18) 0.0439(9) Uani d . 1
H H1 0.4776 -0.1063 0.1230 0.053 Uiso calc R 1
N N2 0.5205(2) 0.0692(2) 0.1274(2) 0.0488(9) Uani d . 1
N N3 0.29121(19) -0.0361(3) 0.1292(2) 0.0476(8) Uani d . 1
C C1 0.6089(3) -0.0896(3) 0.1224(2) 0.0370(9) Uani d . 1
C C2 0.6903(3) -0.1473(3) 0.1211(2) 0.0374(10) Uani d . 1
C C3 0.6870(3) -0.2573(3) 0.1201(2) 0.0528(11) Uani d . 1
H H3 0.7411 -0.2969 0.1191 0.063 Uiso calc R 1
C C4 0.6018(3) -0.3086(3) 0.1207(2) 0.0550(11) Uani d . 1
H H4 0.5986 -0.3828 0.1198 0.066 Uiso calc R 1
C C5 0.5228(3) -0.2490(3) 0.1224(2) 0.0502(11) Uani d . 1
H H5 0.4657 -0.2826 0.1235 0.060 Uiso calc R 1
C C6 0.6062(3) 0.0275(3) 0.1258(2) 0.0380(9) Uani d . 1
C C7 0.6867(3) 0.0879(3) 0.1278(2) 0.0421(10) Uani d . 1
C C8 0.6798(3) 0.1978(3) 0.1312(2) 0.0534(13) Uani d . 1
H H8 0.7320 0.2411 0.1319 0.064 Uiso calc R 1
C C9 0.5922(3) 0.2415(3) 0.1336(2) 0.0589(12) Uani d . 1
H H9 0.5852 0.3151 0.1369 0.071 Uiso calc R 1
C C10 0.5151(3) 0.1749(3) 0.1308(3) 0.0589(13) Uani d . 1
H H10 0.4568 0.2058 0.1314 0.071 Uiso calc R 1
C C11 0.7780(3) 0.0351(4) 0.1244(2) 0.0526(10) Uani d . 1
C C12 0.7807(3) -0.0894(3) 0.1227(2) 0.0469(11) 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 0.0000 0.0000 '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'
N N 0.0061 0.0033 '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
C5 N1 C1 122.7(3)
C5 N1 H1 118.7
C1 N1 H1 118.7
C10 N2 C6 116.6(3)
O3 N3 O4 120.3(3)
O3 N3 O5 120.3(3)
O4 N3 O5 119.4(3)
N1 C1 C2 119.1(4)
N1 C1 C6 117.6(4)
C2 C1 C6 123.3(4)
C3 C2 C1 119.5(4)
C3 C2 C12 121.0(4)
C1 C2 C12 119.5(4)
C2 C3 C4 119.4(4)
C2 C3 H3 120.3
C4 C3 H3 120.3
C5 C4 C3 119.6(4)
C5 C4 H4 120.2
C3 C4 H4 120.2
N1 C5 C4 119.8(4)
N1 C5 H5 120.1
C4 C5 H5 120.1
N2 C6 C7 124.1(4)
N2 C6 C1 114.7(4)
C7 C6 C1 121.2(4)
C8 C7 C6 118.5(4)
C8 C7 C11 120.9(4)
C6 C7 C11 120.5(4)
C7 C8 C9 117.8(4)
C7 C8 H8 121.1
C9 C8 H8 121.1
C8 C9 C10 119.8(4)
C8 C9 H9 120.1
C10 C9 H9 120.1
N2 C10 C9 123.1(4)
N2 C10 H10 118.4
C9 C10 H10 118.4
O2 C11 C7 123.4(5)
O2 C11 C12 118.6(4)
C7 C11 C12 118.0(4)
O1 C12 C2 122.5(4)
O1 C12 C11 120.0(4)
C2 C12 C11 117.5(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C12 1.206(4)
O2 C11 1.210(3)
O3 N3 1.244(3)
O4 N3 1.251(3)
O5 N3 1.256(3)
N1 C5 1.335(4)
N1 C1 1.347(4)
N1 H1 0.8600
N2 C10 1.326(4)
N2 C6 1.350(4)
C1 C2 1.387(4)
C1 C6 1.467(4)
C2 C3 1.377(4)
C2 C12 1.492(4)
C3 C4 1.392(4)
C3 H3 0.9300
C4 C5 1.371(4)
C4 H4 0.9300
C5 H5 0.9300
C6 C7 1.385(4)
C7 C8 1.381(4)
C7 C11 1.488(4)
C8 C9 1.387(4)
C8 H8 0.9300
C9 C10 1.389(4)
C9 H9 0.9300
C10 H10 0.9300
C11 C12 1.559(4)
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 H1 O5 . 0.86 1.95 2.703(4) 145.1
C8 H8 O5 3 0.93 2.48 3.396(4) 167.0
C9 H9 O4 3 0.93 2.71 3.359(5) 127.9
C4 H4 O4 3_545 0.93 2.61 3.323(4) 133.9
C3 H3 O3 3_545 0.93 2.40 3.209(4) 145.8
C10 H10 O1 3_455 0.93 2.47 3.318(5) 150.9
C5 H5 O2 3_445 0.93 2.37 3.266(5) 162.0
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 0.5(5)
C5 N1 C1 C6 -178.2(3)
N1 C1 C2 C3 0.0(5)
C6 C1 C2 C3 178.6(3)
N1 C1 C2 C12 -178.9(3)
C6 C1 C2 C12 -0.3(5)
C1 C2 C3 C4 -0.1(5)
C12 C2 C3 C4 178.7(3)
C2 C3 C4 C5 -0.2(5)
C1 N1 C5 C4 -0.8(5)
C3 C4 C5 N1 0.6(6)
C10 N2 C6 C7 0.2(5)
C10 N2 C6 C1 179.8(3)
N1 C1 C6 N2 -0.9(5)
C2 C1 C6 N2 -179.5(3)
N1 C1 C6 C7 178.7(3)
C2 C1 C6 C7 0.1(5)
N2 C6 C7 C8 -0.3(5)
C1 C6 C7 C8 -179.9(3)
N2 C6 C7 C11 -179.1(3)
C1 C6 C7 C11 1.2(5)
C6 C7 C8 C9 0.7(5)
C11 C7 C8 C9 179.5(3)
C7 C8 C9 C10 -1.0(5)
C6 N2 C10 C9 -0.5(5)
C8 C9 C10 N2 1.0(6)
C8 C7 C11 O2 -0.4(5)
C6 C7 C11 O2 178.4(3)
C8 C7 C11 C12 178.9(3)
C6 C7 C11 C12 -2.3(5)
C3 C2 C12 O1 -0.9(5)
C1 C2 C12 O1 178.0(4)
C3 C2 C12 C11 -179.6(3)
C1 C2 C12 C11 -0.8(4)
O2 C11 C12 O1 2.5(6)
C7 C11 C12 O1 -176.8(3)
O2 C11 C12 C2 -178.6(3)
C7 C11 C12 C2 2.1(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21119531
2 PubChem 139074093
