#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:17:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301807 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/19/2241978.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_2241978
loop_
_publ_author_name
'Safyanova, Inna S.'
'Ohui, Kateryna A.'
'Omelchenko, Irina V.'
_publ_section_title
;
 Crystal structure of
 bis(μ-N-hydroxypicolinamidato)bis[bis(N-hydroxypicolinamide)sodium]
;
_journal_coeditor_code           XU5895
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              24
_journal_page_last               27
_journal_paper_doi               10.1107/S2056989016019095
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          '[Na2 (C6 H5 N2 O2)2 (C6 H6 N2 O2)4]'
_chemical_formula_moiety         'C36 H34 N12 Na2 O12'
_chemical_formula_sum            'C36 H34 N12 Na2 O12'
_chemical_formula_weight         872.73
_chemical_name_systematic
Bis(μ-N-hydroxypicolinamidato)bis[bis(N-hydroxypicolinamide)sodium]
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                96.618(6)
_cell_angle_beta                 102.741(6)
_cell_angle_gamma                113.902(7)
_cell_formula_units_Z            1
_cell_length_a                   9.7997(7)
_cell_length_b                   10.0959(7)
_cell_length_c                   11.0401(8)
_cell_measurement_reflns_used    2896
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      31.5770
_cell_measurement_theta_min      3.2230
_cell_volume                     948.02(14)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2013)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Agilent Xcalibur Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12244
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2013)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.232
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         5521
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.0635
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0618P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1435
_reflns_number_gt                3066
_reflns_number_total             5514
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            xu5895sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        948.02(13)
_cod_database_code               2241978
_cod_database_fobs_code          2241978
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Na Na1 0.46101(9) 0.10567(8) 0.60562(6) 0.0406(2) Uani d 1
O O1 0.23043(17) 0.04309(17) 0.66132(12) 0.0517(4) Uani d 1
O O2 0.33418(18) 0.01016(16) 0.90258(13) 0.0445(4) Uani d 1
H H2 0.426(3) 0.053(3) 0.883(2) 0.066(8) Uiso d 1
O O3 0.56164(19) 0.36282(15) 0.66630(13) 0.0555(4) Uani d 1
O O4 0.74368(18) 0.39266(18) 0.90321(14) 0.0516(4) Uani d 1
H H4 0.681(3) 0.293(3) 0.876(3) 0.107(11) Uiso d 1
O O5 0.39508(16) 0.03347(14) 0.38677(12) 0.0413(3) Uani d 1
O O6 0.42798(15) -0.11024(13) 0.17918(12) 0.0374(3) Uani d 1
N N1 0.2660(2) 0.10347(19) 0.87255(16) 0.0397(4) Uani d 1
H H1 0.250(3) 0.145(3) 0.930(2) 0.075(9) Uiso d 1
N N2 0.1263(2) 0.28298(18) 0.84096(15) 0.0445(4) Uani d 1
N N3 0.6408(2) 0.45461(19) 0.87873(17) 0.0428(4) Uani d 1
H H3 0.643(3) 0.517(3) 0.940(2) 0.068(8) Uiso d 1
N N4 0.4699(2) 0.60614(18) 0.85596(16) 0.0454(4) Uani d 1
N N5 0.34178(18) -0.03212(17) 0.17342(15) 0.0325(4) Uani d 1
H H5 0.301(2) -0.018(2) 0.104(2) 0.049(6) Uiso d 1
N N6 0.16908(19) 0.11506(18) 0.13287(14) 0.0391(4) Uani d 1
C C1 0.1203(2) 0.19678(19) 0.73700(17) 0.0327(4) Uani d 1
C C2 0.0281(3) 0.1793(3) 0.61794(19) 0.0515(6) Uani d 1
H H2A 0.0291 0.1203 0.5472 0.062 Uiso calc 1
C C3 -0.0661(3) 0.2507(3) 0.6045(2) 0.0596(6) Uani d 1
H H3A -0.1316 0.2385 0.5248 0.072 Uiso calc 1
C C4 -0.0623(2) 0.3393(2) 0.7094(2) 0.0483(5) Uani d 1
H H4A -0.1247 0.3889 0.7029 0.058 Uiso calc 1
C C5 0.0357(3) 0.3532(2) 0.8243(2) 0.0522(6) Uani d 1
H H5A 0.0399 0.4154 0.8954 0.063 Uiso calc 1
C C6 0.2119(2) 0.1080(2) 0.75329(17) 0.0337(4) Uani d 1
C C7 0.4699(2) 0.52978(19) 0.74923(18) 0.0358(4) Uani d 1
C C8 0.3960(3) 0.5331(3) 0.6301(2) 0.0583(6) Uani d 1
H H8 0.3977 0.4771 0.5579 0.070 Uiso calc 1
C C9 0.3190(3) 0.6209(3) 0.6188(2) 0.0679(7) Uani d 1
H H9 0.2696 0.6265 0.5387 0.082 Uiso calc 1
C C10 0.3159(3) 0.6994(2) 0.7263(2) 0.0515(6) Uani d 1
H H10 0.2635 0.7584 0.7214 0.062 Uiso calc 1
C C11 0.3925(3) 0.6887(2) 0.8421(2) 0.0502(6) Uani d 1
H H11 0.3905 0.7424 0.9155 0.060 Uiso calc 1
C C12 0.5611(2) 0.44067(19) 0.76097(18) 0.0371(4) Uani d 1
C C13 0.2335(2) 0.11871(18) 0.25376(16) 0.0301(4) Uani d 1
C C14 0.2116(3) 0.1935(3) 0.3547(2) 0.0540(6) Uani d 1
H H14 0.2580 0.1948 0.4382 0.065 Uiso calc 1
C C15 0.1199(3) 0.2665(3) 0.3297(2) 0.0595(6) Uani d 1
H H15 0.1045 0.3184 0.3964 0.071 Uiso calc 1
C C16 0.0524(2) 0.2621(2) 0.2072(2) 0.0431(5) Uani d 1
H H16 -0.0103 0.3101 0.1881 0.052 Uiso calc 1
C C17 0.0792(2) 0.1845(2) 0.11211(19) 0.0465(5) Uani d 1
H H17 0.0316 0.1803 0.0280 0.056 Uiso calc 1
C C18 0.3310(2) 0.03654(18) 0.27692(16) 0.0299(4) 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O5 Na1 O3 . . 109.39(6)
O5 Na1 O1 . . 107.77(5)
O3 Na1 O1 . . 98.10(6)
O5 Na1 O5 . 2_656 86.43(5)
O3 Na1 O5 . 2_656 126.64(6)
O1 Na1 O5 . 2_656 125.87(6)
O5 Na1 O6 . 2_656 156.53(5)
O3 Na1 O6 . 2_656 87.61(5)
O1 Na1 O6 . 2_656 84.80(5)
O5 Na1 O6 2_656 2_656 70.26(5)
C6 O1 Na1 . . 127.13(13)
N1 O2 H2 . . 102.4(15)
C12 O3 Na1 . . 129.55(13)
N3 O4 H4 . . 103.9(19)
C18 O5 Na1 . . 151.93(12)
C18 O5 Na1 . 2_656 114.42(11)
Na1 O5 Na1 . 2_656 93.57(5)
N5 O6 Na1 . 2_656 110.28(9)
C6 N1 O2 . . 121.64(15)
C6 N1 H1 . . 121.1(19)
O2 N1 H1 . . 116.7(19)
C1 N2 C5 . . 116.66(17)
C12 N3 O4 . . 121.18(16)
C12 N3 H3 . . 119.5(17)
O4 N3 H3 . . 118.2(17)
C7 N4 C11 . . 116.62(18)
C18 N5 O6 . . 121.82(15)
C18 N5 H5 . . 116.6(14)
O6 N5 H5 . . 121.3(14)
C17 N6 C13 . . 117.46(16)
N2 C1 C2 . . 123.00(17)
N2 C1 C6 . . 118.12(16)
C2 C1 C6 . . 118.77(16)
C1 C2 C3 . . 118.83(19)
C1 C2 H2A . . 120.6
C3 C2 H2A . . 120.6
C4 C3 C2 . . 119.3(2)
C4 C3 H3A . . 120.3
C2 C3 H3A . . 120.3
C3 C4 C5 . . 117.99(19)
C3 C4 H4A . . 121.0
C5 C4 H4A . . 121.0
N2 C5 C4 . . 124.16(19)
N2 C5 H5A . . 117.9
C4 C5 H5A . . 117.9
O1 C6 N1 . . 123.81(17)
O1 C6 C1 . . 121.78(17)
N1 C6 C1 . . 114.39(16)
N4 C7 C8 . . 123.26(18)
N4 C7 C12 . . 118.11(17)
C8 C7 C12 . . 118.58(17)
C7 C8 C9 . . 118.8(2)
C7 C8 H8 . . 120.6
C9 C8 H8 . . 120.6
C10 C9 C8 . . 119.3(2)
C10 C9 H9 . . 120.4
C8 C9 H9 . . 120.4
C9 C10 C11 . . 118.0(2)
C9 C10 H10 . . 121.0
C11 C10 H10 . . 121.0
N4 C11 C10 . . 124.06(19)
N4 C11 H11 . . 118.0
C10 C11 H11 . . 118.0
O3 C12 N3 . . 123.70(18)
O3 C12 C7 . . 121.61(18)
N3 C12 C7 . . 114.69(16)
N6 C13 C14 . . 122.09(17)
N6 C13 C18 . . 117.42(15)
C14 C13 C18 . . 120.49(17)
C13 C14 C15 . . 118.87(19)
C13 C14 H14 . . 120.6
C15 C14 H14 . . 120.6
C16 C15 C14 . . 119.55(19)
C16 C15 H15 . . 120.2
C14 C15 H15 . . 120.2
C15 C16 C17 . . 118.02(18)
C15 C16 H16 . . 121.0
C17 C16 H16 . . 121.0
N6 C17 C16 . . 124.00(19)
N6 C17 H17 . . 118.0
C16 C17 H17 . . 118.0
O5 C18 N5 . . 123.20(16)
O5 C18 C13 . . 121.78(15)
N5 C18 C13 . . 115.02(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Na1 O5 . 2.3044(14)
Na1 O3 . 2.3225(15)
Na1 O1 . 2.3300(16)
Na1 O5 2_656 2.3558(14)
Na1 O6 2_656 2.3716(14)
Na1 Na1 2_656 3.3964(13)
O1 C6 . 1.232(2)
O2 N1 . 1.388(2)
O2 H2 . 0.91(2)
O3 C12 . 1.235(2)
O4 N3 . 1.383(2)
O4 H4 . 0.91(3)
O5 C18 . 1.247(2)
O5 Na1 2_656 2.3558(14)
O6 N5 . 1.3666(18)
O6 Na1 2_656 2.3716(14)
N1 C6 . 1.320(2)
N1 H1 . 0.80(2)
N2 C1 . 1.333(2)
N2 C5 . 1.339(2)
N3 C12 . 1.319(3)
N3 H3 . 0.86(2)
N4 C7 . 1.332(2)
N4 C11 . 1.336(2)
N5 C18 . 1.314(2)
N5 H5 . 0.84(2)
N6 C17 . 1.330(2)
N6 C13 . 1.334(2)
C1 C2 . 1.367(3)
C1 C6 . 1.503(2)
C2 C3 . 1.377(3)
C2 H2A . 0.9300
C3 C4 . 1.363(3)
C3 H3A . 0.9300
C4 C5 . 1.365(3)
C4 H4A . 0.9300
C5 H5A . 0.9300
C7 C8 . 1.366(3)
C7 C12 . 1.501(3)
C8 C9 . 1.378(3)
C8 H8 . 0.9300
C9 C10 . 1.362(3)
C9 H9 . 0.9300
C10 C11 . 1.372(3)
C10 H10 . 0.9300
C11 H11 . 0.9300
C13 C14 . 1.379(3)
C13 C18 . 1.500(2)
C14 C15 . 1.379(3)
C14 H14 . 0.9300
C15 C16 . 1.355(3)
C15 H15 . 0.9300
C16 C17 . 1.372(3)
C16 H16 . 0.9300
C17 H17 . 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
N1 H1 N2 . 0.80(3) 2.35(3) 2.688(3) 106(2)
N3 H3 N4 . 0.86(3) 2.30(3) 2.681(3) 107(2)
N5 H5 N6 . 0.84(2) 2.25(2) 2.670(3) 111.1(17)
O2 H2 O6 2_656 0.91(2) 1.65(2) 2.549(2) 169(2)
O4 H4 O6 2_656 0.91(3) 1.66(3) 2.5744(19) 177(3)
N1 H1 N6 1_556 0.80(2) 2.55(3) 3.224(2) 143(2)
N5 H5 O2 1_554 0.84(2) 2.35(2) 3.058(2) 142.6(19)
C5 H5A O4 2_667 0.93 2.61 3.341(3) 136.4
C17 H17 N2 1_554 0.93 2.60 3.330(3) 135.7
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_site_symmetry_1
_geom_torsion
Na1 O6 N5 C18 2_656 1.8(2)
C5 N2 C1 C2 . 0.4(3)
C5 N2 C1 C6 . -175.88(18)
N2 C1 C2 C3 . -1.8(3)
C6 C1 C2 C3 . 174.5(2)
C1 C2 C3 C4 . 1.6(4)
C2 C3 C4 C5 . -0.1(4)
C1 N2 C5 C4 . 1.2(3)
C3 C4 C5 N2 . -1.4(4)
Na1 O1 C6 N1 . -72.4(2)
Na1 O1 C6 C1 . 109.31(18)
O2 N1 C6 O1 . -7.4(3)
O2 N1 C6 C1 . 170.99(16)
N2 C1 C6 O1 . -169.34(18)
C2 C1 C6 O1 . 14.2(3)
N2 C1 C6 N1 . 12.2(3)
C2 C1 C6 N1 . -164.23(19)
C11 N4 C7 C8 . 0.0(3)
C11 N4 C7 C12 . 177.53(17)
N4 C7 C8 C9 . 0.8(4)
C12 C7 C8 C9 . -176.6(2)
C7 C8 C9 C10 . -1.3(4)
C8 C9 C10 C11 . 0.9(4)
C7 N4 C11 C10 . -0.5(3)
C9 C10 C11 N4 . 0.0(4)
Na1 O3 C12 N3 . 67.5(3)
Na1 O3 C12 C7 . -113.54(18)
O4 N3 C12 O3 . 6.3(3)
O4 N3 C12 C7 . -172.72(16)
N4 C7 C12 O3 . 177.27(19)
C8 C7 C12 O3 . -5.1(3)
N4 C7 C12 N3 . -3.7(3)
C8 C7 C12 N3 . 173.90(19)
C17 N6 C13 C14 . -1.3(3)
C17 N6 C13 C18 . 178.22(17)
N6 C13 C14 C15 . 0.2(3)
C18 C13 C14 C15 . -179.3(2)
C13 C14 C15 C16 . 0.6(4)
C14 C15 C16 C17 . -0.3(4)
C13 N6 C17 C16 . 1.7(3)
C15 C16 C17 N6 . -0.9(3)
Na1 O5 C18 N5 . 175.36(18)
Na1 O5 C18 N5 2_656 0.2(2)
Na1 O5 C18 C13 . -5.3(4)
Na1 O5 C18 C13 2_656 179.48(12)
O6 N5 C18 O5 . -1.4(3)
O6 N5 C18 C13 . 179.24(14)
N6 C13 C18 O5 . -179.72(17)
C14 C13 C18 O5 . -0.2(3)
N6 C13 C18 N5 . -0.4(2)
C14 C13 C18 N5 . 179.15(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139088248
