#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/42/2214240.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_2214240
loop_
_publ_author_name
'Zeng, Xi-Rui'
'Liu, Yin-Qiu'
'Huang Lin'
'Xu, Ya-Ping'
_publ_section_title
(4,4'-Bipyridyl-κN)tetrakis(nitrato-κ²N,N')[4-(4-pyridyl)pyridinium-κN¹]europium(III)
_journal_coeditor_code           HG2235
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1929
_journal_page_last               m1929
_journal_paper_doi               10.1107/S1600536807022982
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Eu (N O3)4 (C10 H9 N2) (C10 H8 N2)]'
_chemical_formula_moiety         'C20 H17 Eu N8 O12'
_chemical_formula_sum            'C20 H17 Eu N8 O12'
_chemical_formula_weight         713.38
_chemical_name_systematic
;
(4,4'-Bipyridyl-\kN)[4'-(4-pyridyl)pyridinium-\kN^1'^]tetrakis(nitrato-
κ²N,N')europium(III)
;
_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                 118.834(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.136(5)
_cell_length_b                   7.8079(14)
_cell_length_c                   18.310(3)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.40
_cell_measurement_theta_min      2.10
_cell_volume                     2521.8(9)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    SHELXL97
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEXII area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0512
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7437
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         2.31
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.568
_exptl_absorpt_correction_T_max  0.6185
_exptl_absorpt_correction_T_min  0.5334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.879
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.556
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2211
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0185
_refine_ls_R_factor_gt           0.0179
_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)+(0.031P)²+0.9897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0487
_refine_ls_wR_factor_ref         0.0489
_reflns_number_gt                2153
_reflns_number_total             2211
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2235.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2214240
_cod_database_fobs_code          2214240
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
_atom_site_disorder_assembly
_atom_site_disorder_group
H H11 0.243(7) 1.222(16) 0.018(7) 0.13(5) Uiso d PD 0.50(10) A 1
Eu Eu1 0.0000 0.338536(17) 0.2500 0.03085(8) Uani d S 1 . .
O O4 0.00208(11) 0.3047(3) 0.11446(11) 0.0480(4) Uani d . 1 . .
O O3 0.12196(11) 0.2141(3) 0.27142(11) 0.0468(4) Uani d . 1 . .
O O6 -0.09200(10) 0.4418(2) 0.11018(11) 0.0478(4) Uani d . 1 . .
N N2 -0.05805(13) 0.3852(3) 0.07139(12) 0.0427(5) Uani d . 1 . .
N N1 0.12672(12) 0.0900(3) 0.31810(12) 0.0407(5) Uani d . 1 . .
O O1 0.07166(11) 0.0719(3) 0.33171(13) 0.0554(5) Uani d . 1 . .
O O2 0.18155(12) -0.0037(3) 0.34727(12) 0.0622(5) Uani d . 1 . .
O O5 -0.08280(14) 0.4120(3) -0.00236(11) 0.0702(6) Uani d . 1 . .
N N3 0.06444(12) 0.6021(3) 0.22022(12) 0.0399(4) Uani d . 1 . .
C C3 0.12606(15) 0.8304(3) 0.15042(14) 0.0340(5) Uani d . 1 . .
C C4 0.05361(16) 0.8533(3) 0.13925(16) 0.0396(6) Uani d . 1 . .
H H4 0.0244 0.9459 0.1087 0.048 Uiso calc R 1 . .
C C2 0.16818(15) 0.6951(3) 0.19990(15) 0.0412(5) Uani d . 1 . .
H H2 0.2178 0.6777 0.2108 0.049 Uiso calc R 1 . .
C C5 0.02512(15) 0.7364(3) 0.17410(15) 0.0411(5) Uani d . 1 . .
H H5 -0.0241 0.7521 0.1649 0.049 Uiso calc R 1 . .
C C1 0.13539(14) 0.5861(4) 0.23286(15) 0.0437(6) Uani d . 1 . .
H H1 0.1645 0.4959 0.2660 0.052 Uiso calc R 1 . .
C C6 0.15731(13) 0.9448(3) 0.10950(13) 0.0347(5) Uani d . 1 . .
C C7 0.20534(15) 0.8784(4) 0.08172(15) 0.0399(5) Uani d . 1 . .
H H7 0.2178 0.7627 0.0882 0.048 Uiso calc R 1 . .
C C10 0.13999(17) 1.1166(4) 0.09719(19) 0.0509(7) Uani d . 1 . .
H H10 0.1071 1.1645 0.1138 0.061 Uiso calc R 1 . .
N N4 0.21769(15) 1.1517(3) 0.03422(15) 0.0461(6) Uani d D 1 . .
C C8 0.23413(14) 0.9869(4) 0.04437(15) 0.0444(6) Uani d . 1 . .
H H8 0.2661 0.9424 0.0257 0.053 Uiso calc R 1 . .
C C9 0.17182(18) 1.2178(4) 0.05995(19) 0.0571(7) Uani d . 1 . .
H H9 0.1608 1.3343 0.0529 0.068 Uiso calc R 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.1578 3.6682 '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
O6 Eu1 O6 2 . 141.76(9)
O6 Eu1 O3 2 . 76.92(6)
O6 Eu1 O3 . . 118.81(6)
O6 Eu1 O3 2 2 118.81(6)
O6 Eu1 O3 . 2 76.92(6)
O3 Eu1 O3 . 2 134.06(10)
O6 Eu1 O4 2 2 51.01(6)
O6 Eu1 O4 . 2 134.26(7)
O3 Eu1 O4 . 2 106.74(6)
O3 Eu1 O4 2 2 68.29(6)
O6 Eu1 O4 2 . 134.26(7)
O6 Eu1 O4 . . 51.01(6)
O3 Eu1 O4 . . 68.29(6)
O3 Eu1 O4 2 . 106.74(6)
O4 Eu1 O4 2 . 167.96(9)
O6 Eu1 O1 2 2 143.35(6)
O6 Eu1 O1 . 2 74.31(7)
O3 Eu1 O1 . 2 90.56(6)
O3 Eu1 O1 2 2 49.94(6)
O4 Eu1 O1 2 2 102.59(6)
O4 Eu1 O1 . 2 67.15(7)
O6 Eu1 O1 2 . 74.31(7)
O6 Eu1 O1 . . 143.35(6)
O3 Eu1 O1 . . 49.94(6)
O3 Eu1 O1 2 . 90.56(6)
O4 Eu1 O1 2 . 67.14(7)
O4 Eu1 O1 . . 102.60(6)
O1 Eu1 O1 2 . 71.41(10)
O6 Eu1 N3 2 . 76.11(6)
O6 Eu1 N3 . . 74.15(7)
O3 Eu1 N3 . . 77.88(7)
O3 Eu1 N3 2 . 145.24(7)
O4 Eu1 N3 2 . 122.13(6)
O4 Eu1 N3 . . 68.44(7)
O1 Eu1 N3 2 . 135.27(6)
O1 Eu1 N3 . . 124.20(7)
O6 Eu1 N3 2 2 74.15(7)
O6 Eu1 N3 . 2 76.11(6)
O3 Eu1 N3 . 2 145.24(7)
O3 Eu1 N3 2 2 77.88(7)
O4 Eu1 N3 2 2 68.44(7)
O4 Eu1 N3 . 2 122.13(6)
O1 Eu1 N3 2 2 124.20(6)
O1 Eu1 N3 . 2 135.27(6)
N3 Eu1 N3 . 2 76.83(9)
O6 Eu1 N2 2 2 25.77(6)
O6 Eu1 N2 . 2 144.95(6)
O3 Eu1 N2 . 2 92.34(6)
O3 Eu1 N2 2 2 93.26(6)
O4 Eu1 N2 2 2 25.24(6)
O4 Eu1 N2 . 2 158.55(7)
O1 Eu1 N2 2 2 124.35(7)
O1 Eu1 N2 . 2 68.82(7)
N3 Eu1 N2 . 2 99.43(6)
N3 Eu1 N2 2 2 68.91(6)
O6 Eu1 N1 2 2 135.74(6)
O6 Eu1 N1 . 2 73.34(6)
O3 Eu1 N1 . 2 113.25(7)
O3 Eu1 N1 2 2 24.97(6)
O4 Eu1 N1 2 2 85.74(6)
O4 Eu1 N1 . 2 86.37(6)
O1 Eu1 N1 2 2 24.99(6)
O1 Eu1 N1 . 2 80.89(6)
N3 Eu1 N1 . 2 146.93(6)
N3 Eu1 N1 2 2 100.91(7)
N2 Eu1 N1 2 2 110.62(6)
N2 O4 Eu1 . . 95.61(13)
N1 O3 Eu1 . . 98.80(14)
N2 O6 Eu1 . . 97.39(14)
O5 N2 O4 . . 122.9(2)
O5 N2 O6 . . 121.1(2)
O4 N2 O6 . . 115.97(19)
O2 N1 O1 . . 123.2(2)
O2 N1 O3 . . 121.1(2)
O1 N1 O3 . . 115.7(2)
N1 O1 Eu1 . . 95.47(13)
C1 N3 C5 . . 116.0(2)
C1 N3 Eu1 . . 118.97(17)
C5 N3 Eu1 . . 122.90(16)
C4 C3 C2 . . 117.7(2)
C4 C3 C6 . . 121.4(2)
C2 C3 C6 . . 120.9(2)
C3 C4 C5 . . 119.2(2)
C3 C4 H4 . . 120.4
C5 C4 H4 . . 120.4
C1 C2 C3 . . 119.0(2)
C1 C2 H2 . . 120.5
C3 C2 H2 . . 120.5
N3 C5 C4 . . 123.7(2)
N3 C5 H5 . . 118.1
C4 C5 H5 . . 118.1
N3 C1 C2 . . 124.2(2)
N3 C1 H1 . . 117.9
C2 C1 H1 . . 117.9
C10 C6 C7 . . 117.9(2)
C10 C6 C3 . . 122.2(2)
C7 C6 C3 . . 119.9(2)
C8 C7 C6 . . 119.0(3)
C8 C7 H7 . . 120.5
C6 C7 H7 . . 120.5
C6 C10 C9 . . 119.7(3)
C6 C10 H10 . . 120.2
C9 C10 H10 . . 120.2
C8 N4 C9 . . 120.0(2)
C8 N4 H11 . . 120(10)
C9 N4 H11 . . 119(10)
N4 C8 C7 . . 122.1(2)
N4 C8 H8 . . 118.9
C7 C8 H8 . . 118.9
N4 C9 C10 . . 121.3(3)
N4 C9 H9 . . 119.4
C10 C9 H9 . . 119.4
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
Eu1 O6 2 2.4620(18) yes
Eu1 O6 . 2.4620(18) ?
Eu1 O3 . 2.4900(19) yes
Eu1 O3 2 2.4900(19) ?
Eu1 O4 2 2.5159(18) yes
Eu1 O4 . 2.5160(18) ?
Eu1 O1 2 2.563(2) yes
Eu1 O1 . 2.563(2) ?
Eu1 N3 . 2.626(2) yes
Eu1 N3 2 2.626(2) ?
Eu1 N2 2 2.917(2) yes
Eu1 N1 2 2.960(2) yes
O4 N2 . 1.250(3) ?
O3 N1 . 1.265(3) ?
O6 N2 . 1.279(3) ?
N2 O5 . 1.211(3) ?
N1 O2 . 1.213(3) ?
N1 O1 . 1.256(3) ?
N3 C1 . 1.338(3) ?
N3 C5 . 1.340(4) ?
C3 C4 . 1.383(4) ?
C3 C2 . 1.384(3) ?
C3 C6 . 1.487(3) ?
C4 C5 . 1.386(3) ?
C4 H4 . 0.9300 ?
C2 C1 . 1.381(4) ?
C2 H2 . 0.9300 ?
C5 H5 . 0.9300 ?
C1 H1 . 0.9300 ?
C6 C10 . 1.377(4) ?
C6 C7 . 1.392(3) ?
C7 C8 . 1.380(4) ?
C7 H7 . 0.9300 ?
C10 C9 . 1.386(4) ?
C10 H10 . 0.9300 ?
N4 C8 . 1.319(4) ?
N4 C9 . 1.327(4) ?
N4 H11 . 0.89(2) ?
C8 H8 . 0.9300 ?
C9 H9 . 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
N4 H11 N4 7_575 0.89(6) 1.80(6) 2.682(4) 169(6)
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
O6 Eu1 O4 N2 2 -127.84(16)
O6 Eu1 O4 N2 . 0.63(14)
O3 Eu1 O4 N2 . -171.12(17)
O3 Eu1 O4 N2 2 57.44(17)
O4 Eu1 O4 N2 2 121.24(16)
O1 Eu1 O4 N2 2 88.55(16)
O1 Eu1 O4 N2 . 151.89(15)
N3 Eu1 O4 N2 . -86.04(16)
N3 Eu1 O4 N2 2 -28.55(19)
N2 Eu1 O4 N2 2 -144.4(2)
N1 Eu1 O4 N2 2 72.07(16)
O6 Eu1 O3 N1 2 78.56(15)
O6 Eu1 O3 N1 . -139.02(14)
O3 Eu1 O3 N1 2 -39.07(13)
O4 Eu1 O3 N1 2 36.66(16)
O4 Eu1 O3 N1 . -131.72(16)
O1 Eu1 O3 N1 2 -66.67(15)
O1 Eu1 O3 N1 . -1.81(13)
N3 Eu1 O3 N1 . 156.89(16)
N3 Eu1 O3 N1 2 112.80(16)
N2 Eu1 O3 N1 2 57.74(15)
N1 Eu1 O3 N1 2 -55.91(18)
O6 Eu1 O6 N2 2 114.43(15)
O3 Eu1 O6 N2 . 8.13(17)
O3 Eu1 O6 N2 2 -125.26(15)
O4 Eu1 O6 N2 2 -166.10(13)
O4 Eu1 O6 N2 . -0.62(14)
O1 Eu1 O6 N2 2 -73.66(15)
O1 Eu1 O6 N2 . -52.45(19)
N3 Eu1 O6 N2 . 74.22(15)
N3 Eu1 O6 N2 2 154.21(16)
N2 Eu1 O6 N2 2 158.00(15)
N1 Eu1 O6 N2 2 -99.67(15)
Eu1 O4 N2 O5 . 177.7(2)
Eu1 O4 N2 O6 . -1.0(2)
Eu1 O6 N2 O5 . -177.7(2)
Eu1 O6 N2 O4 . 1.1(2)
Eu1 O3 N1 O2 . -176.7(2)
Eu1 O3 N1 O1 . 3.1(2)
O2 N1 O1 Eu1 . 176.8(2)
O3 N1 O1 Eu1 . -3.0(2)
O6 Eu1 O1 N1 2 -84.12(15)
O6 Eu1 O1 N1 . 87.49(17)
O3 Eu1 O1 N1 . 1.81(13)
O3 Eu1 O1 N1 2 156.02(14)
O4 Eu1 O1 N1 2 -137.91(16)
O4 Eu1 O1 N1 . 48.72(15)
O1 Eu1 O1 N1 2 109.05(16)
N3 Eu1 O1 N1 . -23.62(17)
N3 Eu1 O1 N1 2 -130.75(14)
N2 Eu1 O1 N1 2 -110.70(15)
N1 Eu1 O1 N1 2 132.90(14)
O6 Eu1 N3 C1 2 73.72(18)
O6 Eu1 N3 C1 . -130.59(19)
O3 Eu1 N3 C1 . -5.60(17)
O3 Eu1 N3 C1 2 -165.32(15)
O4 Eu1 N3 C1 2 96.69(18)
O4 Eu1 N3 C1 . -76.82(18)
O1 Eu1 N3 C1 2 -83.9(2)
O1 Eu1 N3 C1 . 14.0(2)
N3 Eu1 N3 C1 2 150.4(2)
N2 Eu1 N3 C1 2 84.77(18)
N1 Eu1 N3 C1 2 -119.82(18)
O6 Eu1 N3 C5 2 -123.43(19)
O6 Eu1 N3 C5 . 32.26(18)
O3 Eu1 N3 C5 . 157.24(19)
O3 Eu1 N3 C5 2 -2.5(2)
O4 Eu1 N3 C5 2 -100.46(19)
O4 Eu1 N3 C5 . 86.02(18)
O1 Eu1 N3 C5 2 78.9(2)
O1 Eu1 N3 C5 . 176.88(17)
N3 Eu1 N3 C5 2 -46.80(16)
N2 Eu1 N3 C5 2 -112.38(18)
N1 Eu1 N3 C5 2 43.0(2)
C2 C3 C4 C5 . -3.2(4)
C6 C3 C4 C5 . 175.7(2)
C4 C3 C2 C1 . 2.5(4)
C6 C3 C2 C1 . -176.3(2)
C1 N3 C5 C4 . 1.0(4)
Eu1 N3 C5 C4 . -162.3(2)
C3 C4 C5 N3 . 1.4(4)
C5 N3 C1 C2 . -1.8(4)
Eu1 N3 C1 C2 . 162.2(2)
C3 C2 C1 N3 . 0.0(4)
C4 C3 C6 C10 . 34.9(4)
C2 C3 C6 C10 . -146.3(3)
C4 C3 C6 C7 . -144.6(2)
C2 C3 C6 C7 . 34.2(3)
C10 C6 C7 C8 . 0.8(4)
C3 C6 C7 C8 . -179.6(2)
C7 C6 C10 C9 . -1.6(4)
C3 C6 C10 C9 . 178.9(3)
C9 N4 C8 C7 . -0.3(4)
C6 C7 C8 N4 . 0.1(4)
C8 N4 C9 C10 . -0.4(5)
C6 C10 C9 N4 . 1.4(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139072476
