#------------------------------------------------------------------------------
#$Date: 2022-10-03 17:40:12 +0300 (Mon, 03 Oct 2022) $
#$Revision: 278324 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/02/2010267.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_2010267
loop_
_publ_author_name
'Sommerer, S.O.'
'Westcott, B.L.'
'Friebe, T.L.'
'Abboud, K.A.'
_publ_section_title
;
 Di(2-pyridinio)methanediol dinitrate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2013
_journal_page_last               2015
_journal_paper_doi               10.1107/S0108270194004488
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C11 H12 N2 O2 2+,  2N O3 1-'
_chemical_formula_sum            'C11 H12 N4 O8'
_chemical_formula_weight         328.25
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.
_cell_angle_beta                 100.38(2)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   10.292(2)
_cell_length_b                   11.2190(10)
_cell_length_c                   12.481(2)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    295
_cell_measurement_theta_max      11
_cell_measurement_theta_min      10
_cell_volume                     1417.5(4)
_diffrn_measurement_device       'Siemens R3m/V'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0138
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4597
_diffrn_reflns_theta_max         30
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 100
_diffrn_standards_number         4
_exptl_absorpt_coefficient_mu    0.13
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   analytical
_exptl_crystal_colour            orange-yellow
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_description       blocks
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   2.03
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     256
_refine_ls_number_reflns         2906
_refine_ls_R_factor_obs          0.0481
_refine_ls_shift/esd_max         0.001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(F) + 0.0004F]²'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0617
_reflns_number_observed          2906
_reflns_number_total             4174
_reflns_observed_criterion       F>4\s(F)
_cod_data_source_file            cr1106.cif
_cod_data_source_block           cr1106a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/[\s^2^(F) + 0.0004F]^2^' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w = 1/[\s^2^(F) +
0.0004F]^2^'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2010267
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 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
N1 .22771(13) .39427(14) .32551(12) .0399(4)
N1' .59761(13) .24926(13) .20434(12) .0367(4)
O1a .47614(13) .44805(13) .18028(12) .0545(5)
O1b .47018(12) .45487(12) .36585(11) .0520(5)
C1 .4450(2) .3889(2) .26970(14) .0388(5)
C2 .2983(2) .3551(2) .25287(13) .0365(5)
C2' .52694(14) .27462(14) .28178(13) .0360(5)
C3 .2387(2) .2845(2) .1693(2) .0480(6)
C3' .5315(2) .1987(2) .3685(2) .0495(6)
C4 .1076(2) .2528(2) .1630(2) .0530(6)
C4' .6139(2) .1014(2) .3772(2) .0625(8)
C5 .0383(2) .2940(2) .2393(2) .0539(7)
C5' .6894(2) .0801(2) .2985(2) .0599(8)
C6 .0998(2) .3653(2) .3206(2) .0510(6)
C6' .6781(2) .1544(2) .2116(2) .0470(6)
N' .2214(2) .14352(14) .47851(12) .0467(5)
O1' .1120(2) .1364(2) .50440(14) .0861(7)
O2' .3080(2) .2048(2) .53228(14) .0808(7)
O3' .2416(2) .0888(2) .39624(12) .0655(6)
N .18931(13) .58795(13) .53806(12) .0416(5)
O1 .1977(2) .6294(2) .62979(13) .0701(6)
O2 .09190(14) .6014(2) .46737(12) .0675(6)
O3 .28523(12) .5263(2) .51775(11) .0645(5)
H1 .264(2) .433(2) .381(2) .051(6)
H1' .591(2) .294(2) .149(2) .046(5)
H1a .417(3) .502(2) .154(2) .078(8)
H1b .553(3) .457(2) .396(2) .071(7)
H3 .288(2) .258(2) .124(2) .055(6)
H3' .480(2) .217(2) .422(2) .063(6)
H4 .065(2) .196(2) .109(2) .059(6)
H4' .618(2) .048(2) .439(2) .064(6)
H5 -.051(2) .273(2) .241(2) .063(6)
H5' .749(2) .019(2) .306(2) .069(7)
H6 .064(2) .401(2) .377(2) .066(6)
H6' .719(2) .147(2) .157(2) .055(6)
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
C2 N1 C6 122.5(2) yes
C2' N1' C6' 121.9(2) yes
C2 C1 C2' 108.57(13) yes
C2 C1 O1a 111.90(13) yes
C2 C1 O1b 105.95(14) yes
C2' C1 O1a 106.15(14) yes
C2' C1 O1b 110.31(13) yes
O1a C1 O1b 113.89(14) yes
C3 C2 N1 119.0(2) yes
C3 C2 C1 123.0(2) yes
N1 C2 C1 117.95(14) yes
C3' C2' N1' 119.4(2) yes
C3' C2' C1 122.6(2) yes
N1' C2' C1 117.95(15) yes
C4 C3 C2 119.5(2) yes
C4' C3' C2' 119.3(2) yes
C5 C4 C3 119.9(2) yes
C5' C4' C3' 120.0(2) yes
C6 C5 C4 119.2(2) yes
C6' C5' C4' 119.0(2) yes
N1 C6 C5 119.9(2) yes
N1' C6' C5' 120.3(2) yes
O1' N' O2' 120.2(2) yes
O2' N' O3' 121.0(2) yes
O3' N' O1' 118.8(2) yes
O1 N O2 122.7(2) yes
O2 N O3 119.4(2) yes
O3 N O1 117.90(14) yes
H1 N1 C2 121.(2) no
H1 N1 C6 116.(2) no
H1' N1' C2' 119.5(14) no
H1' N1' C6' 118.6(15) no
H1a O1a C1 112.(2) no
H1b O1b C1 114.(2) no
H3 C3 C4 123.4(13) no
H3 C3 C2 116.9(13) no
H3' C3' C4' 122.1(13) no
H3' C3' C2' 118.5(13) no
H4 C4 C5 118.6(14) no
H4 C4 C3 121.3(14) no
H4' C4' C5' 120.6(15) no
H4' C4' C3' 119.4(15) no
H5 C5 C6 116.7(13) no
H5 C5 C4 124.0(13) no
H5' C5' C6' 120.(2) no
H5' C5' C4' 120.(2) no
H6 C6 N1 112.0(14) no
H6 C6 C5 128.1(14) no
H6' C6' N1' 113.9(14) no
H6' C6' C5' 125.8(14) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C2 N1 1.335(2) yes
C6 N1 1.346(2) yes
C2' N1' 1.341(2) yes
C6' N1' 1.342(2) yes
C1 O1a 1.385(2) yes
C1 O1b 1.394(2) yes
C2 C1 1.534(2) yes
C2' C1 1.527(2) yes
C3 C2 1.364(2) yes
C3' C2' 1.371(3) yes
C4 C3 1.383(3) yes
C4' C3' 1.374(3) yes
C5 C4 1.369(3) yes
C5' C4' 1.379(4) yes
C6 C5 1.356(3) yes
C6' C5' 1.356(3) yes
O1' N' 1.228(3) yes
O2' N' 1.226(2) yes
O3' N' 1.246(2) yes
O1 N 1.224(2) yes
O2 N 1.220(2) yes
O3 N 1.268(2) yes
H1 N1 0.84(2) no
H1' N1' 0.85(2) no
H1a O1a 0.88(3) no
H1b O1b 0.87(3) no
H3 C3 0.88(2) no
H3' C3' 0.94(3) no
H4 C4 0.98(2) no
H4' C4' 0.97(2) no
H5 C5 0.95(2) no
H5' C5' 0.91(2) no
H6 C6 0.94(2) no
H6' C6' 0.86(2) no
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
C2 C1 C2' N1' 114.6(2) yes
C2' C1 C2 N1 120.0(2) yes
O1a C1 C2 N1 -123.2(2) yes
O1a C1 C2' N1' -5.9(2) yes
O1b C1 C2 N1 1.5(2) yes
O1b C1 C2' N1' -129.8(2) yes
