#------------------------------------------------------------------------------
#$Date: 2021-02-05 01:09:48 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261648 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/58/7705814.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7705814
loop_
_publ_author_name
'Dermitzaki, Despina'
'Raptopoulou, Catherine P.'
'Psycharis, Vassilis'
'Escuer, Albert'
'Perlepes, Spyros P.'
'Mayans, Julia'
'Stamatatos, Theocharis C.'
_publ_section_title
;
 Further synthetic investigation of the general lanthanoid(iii)
 [Ln(iii)]/copper(ii)/pyridine-2,6-dimethanol/carboxylate reaction system:
 {CuLn} coordination clusters (Ln = Dy, Tb, Ho) and their yttrium(iii)
 analogue.
;
_journal_issue                   1
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              240
_journal_page_last               251
_journal_paper_doi               10.1039/d0dt03582c
_journal_volume                  50
_journal_year                    2021
_chemical_formula_moiety         'C~8~H~4~O~4~^2-^, 2(C~3~H~5~N~2~^+^)'
_chemical_formula_sum            'C14 H14 N4 O4'
_chemical_formula_weight         302.29
_chemical_melting_point          462.5(5)
_chemical_name_systematic        bis(Imidazolium)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-10-15 deposited with the CCDC.	2020-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.017(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6205(6)
_cell_length_b                   8.0817(4)
_cell_length_c                   9.8959(6)
_cell_measurement_reflns_used    3969
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.1320
_cell_measurement_theta_min      3.3660
_cell_volume                     702.79(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia 2012)'
_computing_publication_material
;
WINGX (Farrugia, 2012), OLEX2 (Dolomanov et al., 2009) and PLATON
(Spek 2009)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.3991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9694
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.525
_diffrn_reflns_theta_min         2.490
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1798
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0373
_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)+(0.0348P)²+0.3854P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1567
_reflns_number_total             1798
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt03582c2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '462-463 K' was changed to
'462.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7705813--7705815.cif.
;
_cod_original_cell_volume        702.80(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7705814
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_res_file
;
TITL al_imid-tereftal_100_fiol_a.res in P2(1)/n
    shelx.res
    created by SHELXL-2018/3 at 13:08:15 on 14-Oct-2020
CELL 0.71073 9.620531 8.081727 9.895868 90 114.0168 90
ZERR 2 0.000626 0.000388 0.00063 0 0.0076 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 28 28 8 8

L.S. 10
PLAN  5
TEMP -173
CONF
BOND $H
list 4
fmap 2
acta
MORE -1

WGHT    0.034800    0.385400
FVAR       8.46187
O1A   4    0.472945    0.668363    0.646541    11.00000    0.02071    0.02888 =
         0.01222    0.00561    0.00578   -0.00215
O2A   4    0.273069    0.501683    0.600350    11.00000    0.01769    0.02379 =
         0.00971   -0.00188    0.00297   -0.00058
C1A   1    0.393882    0.571067    0.685046    11.00000    0.01551    0.01623 =
         0.01065    0.00038    0.00541    0.00419
C2A   1    0.448943    0.534738    0.848790    11.00000    0.01439    0.01611 =
         0.00958    0.00029    0.00484    0.00264
C3A   1    0.391105    0.399768    0.896587    11.00000    0.01483    0.01609 =
         0.01097   -0.00195    0.00378   -0.00075
AFIX  43
H3A   2    0.316499    0.331009    0.826158    11.00000   -1.20000
AFIX   0
C4A   1    0.441741    0.364798    1.046751    11.00000    0.01620    0.01503 =
         0.01310    0.00099    0.00662   -0.00112
AFIX  43
H4A   2    0.401785    0.272236    1.078299    11.00000   -1.20000
AFIX   0

N1B   3    0.441899    0.808776    0.395401    11.00000    0.01931    0.02352 =
         0.01106    0.00350    0.00566    0.00045
H1B   2    0.439065    0.752604    0.477204    11.00000    0.03844
N2B   3    0.370669    0.925905    0.181563    11.00000    0.01853    0.01993 =
         0.01098    0.00187    0.00515    0.00094
H2B   2    0.306127    0.962393    0.086702    11.00000    0.03283
C1B   1    0.322241    0.846024    0.271892    11.00000    0.01842    0.02440 =
         0.01241    0.00148    0.00600   -0.00032
AFIX  43
H1BA  2    0.219318    0.820006    0.251446    11.00000   -1.20000
AFIX   0
C2B   1    0.526032    0.939891    0.249203    11.00000    0.01732    0.01915 =
         0.01528    0.00087    0.00690    0.00048
AFIX  43
H2BA  2    0.590135    0.991009    0.209507    11.00000   -1.20000
AFIX   0
C3B   1    0.570559    0.866791    0.383541    11.00000    0.01679    0.02030 =
         0.01487    0.00095    0.00515    0.00136
AFIX  43
H3B   2    0.671972    0.857437    0.456034    11.00000   -1.20000

AFIX   0
HKLF 4




REM  al_imid-tereftal_100_fiol_a.res in P2(1)/n
REM wR2 = 0.0942, GooF = S = 1.090, Restrained GooF = 1.090 for all data
REM R1 = 0.0373 for 1567 Fo > 4sig(Fo) and 0.0448 for all 1798 data
REM 108 parameters refined using 0 restraints

END

WGHT      0.0348      0.3852

REM Highest difference peak  0.366,  deepest hole -0.232,  1-sigma level  0.048
Q1    1   0.4183  0.5540  0.7694  11.00000  0.05    0.37
Q2    1   0.4230  0.4771  0.8758  11.00000  0.05    0.26
Q3    1   0.5575  0.9126  0.3215  11.00000  0.05    0.26
Q4    1   0.4176  0.3854  0.9730  11.00000  0.05    0.25
Q5    1   0.4918  0.5828  0.9019  11.00000  0.05    0.23
;
_shelx_res_checksum              58045
loop_
_space_group_symop_operation_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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.47294(10) 0.66836(12) 0.64654(9) 0.0209(2) Uani 1 1 d . . . . .
O2A O 0.27307(10) 0.50168(11) 0.60035(9) 0.0179(2) Uani 1 1 d . . . . .
C1A C 0.39388(13) 0.57107(14) 0.68505(12) 0.0141(2) Uani 1 1 d . . . . .
C2A C 0.44894(13) 0.53474(14) 0.84879(12) 0.0134(2) Uani 1 1 d . . . . .
C3A C 0.39110(13) 0.39977(14) 0.89659(12) 0.0144(2) Uani 1 1 d . . . . .
H3A H 0.316499 0.331009 0.826158 0.017 Uiso 1 1 calc R U . . .
C4A C 0.44174(13) 0.36480(15) 1.04675(12) 0.0146(2) Uani 1 1 d . . . . .
H4A H 0.401785 0.272236 1.078299 0.017 Uiso 1 1 calc R U . . .
N1B N 0.44190(12) 0.80878(14) 0.39540(11) 0.0181(2) Uani 1 1 d . . . . .
H1B H 0.439(2) 0.753(2) 0.477(2) 0.038(5) Uiso 1 1 d . . . . .
N2B N 0.37067(12) 0.92591(13) 0.18156(11) 0.0168(2) Uani 1 1 d . . . . .
H2B H 0.3061(19) 0.962(2) 0.087(2) 0.033(4) Uiso 1 1 d . . . . .
C1B C 0.32224(14) 0.84602(16) 0.27189(13) 0.0185(3) Uani 1 1 d . . . . .
H1BA H 0.219318 0.820006 0.251446 0.022 Uiso 1 1 calc R U . . .
C2B C 0.52603(13) 0.93989(15) 0.24920(13) 0.0172(2) Uani 1 1 d . . . . .
H2BA H 0.590135 0.991009 0.209507 0.021 Uiso 1 1 calc R U . . .
C3B C 0.57056(14) 0.86679(16) 0.38354(13) 0.0177(3) Uani 1 1 d . . . . .
H3B H 0.671972 0.857437 0.456034 0.021 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1A 0.0207(4) 0.0289(5) 0.0122(4) 0.0056(3) 0.0058(3) -0.0021(4)
O2A 0.0177(4) 0.0238(5) 0.0097(4) -0.0019(3) 0.0030(3) -0.0006(3)
C1A 0.0155(5) 0.0162(5) 0.0106(5) 0.0004(4) 0.0054(4) 0.0042(4)
C2A 0.0144(5) 0.0161(5) 0.0096(5) 0.0003(4) 0.0048(4) 0.0026(4)
C3A 0.0148(5) 0.0161(5) 0.0110(5) -0.0019(4) 0.0038(4) -0.0007(4)
C4A 0.0162(5) 0.0150(5) 0.0131(5) 0.0010(4) 0.0066(4) -0.0011(4)
N1B 0.0193(5) 0.0235(5) 0.0111(5) 0.0035(4) 0.0057(4) 0.0004(4)
N2B 0.0185(5) 0.0199(5) 0.0110(5) 0.0019(4) 0.0052(4) 0.0009(4)
C1B 0.0184(6) 0.0244(6) 0.0124(5) 0.0015(5) 0.0060(5) -0.0003(5)
C2B 0.0173(6) 0.0192(6) 0.0153(6) 0.0009(4) 0.0069(5) 0.0005(4)
C3B 0.0168(5) 0.0203(6) 0.0149(6) 0.0010(4) 0.0051(4) 0.0014(5)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2A C1A O1A 125.99(10) . . ?
O2A C1A C2A 116.97(10) . . ?
O1A C1A C2A 117.04(10) . . ?
C3A C2A C4A 119.28(10) . 3_667 ?
C3A C2A C1A 120.09(10) . . ?
C4A C2A C1A 120.63(10) 3_667 . ?
C4A C3A C2A 120.50(10) . . ?
C4A C3A H3A 119.8 . . ?
C2A C3A H3A 119.8 . . ?
C3A C4A C2A 120.23(11) . 3_667 ?
C3A C4A H4A 119.9 . . ?
C2A C4A H4A 119.9 3_667 . ?
C1B N1B C3B 108.54(10) . . ?
C1B N1B H1B 125.8(11) . . ?
C3B N1B H1B 125.7(11) . . ?
C1B N2B C2B 108.79(10) . . ?
C1B N2B H2B 123.7(11) . . ?
C2B N2B H2B 127.5(11) . . ?
N1B C1B N2B 108.58(11) . . ?
N1B C1B H1BA 125.7 . . ?
N2B C1B H1BA 125.7 . . ?
C3B C2B N2B 106.83(11) . . ?
C3B C2B H2BA 126.6 . . ?
N2B C2B H2BA 126.6 . . ?
C2B C3B N1B 107.27(11) . . ?
C2B C3B H3B 126.4 . . ?
N1B C3B H3B 126.4 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C1A 1.2562(15) . ?
O2A C1A 1.2549(14) . ?
C1A C2A 1.5145(15) . ?
C2A C3A 1.3919(16) . ?
C2A C4A 1.3960(16) 3_667 ?
C3A C4A 1.3914(16) . ?
C3A H3A 0.9500 . ?
C4A H4A 0.9500 . ?
N1B C1B 1.3283(16) . ?
N1B C3B 1.3726(16) . ?
N1B H1B 0.938(19) . ?
N2B C1B 1.3311(16) . ?
N2B C2B 1.3713(16) . ?
N2B H2B 0.938(18) . ?
C1B H1BA 0.9500 . ?
C2B C3B 1.3551(17) . ?
C2B H2BA 0.9500 . ?
C3B H3B 0.9500 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2A C1A C2A C3A 16.27(16) . . . . ?
O1A C1A C2A C3A -164.02(11) . . . . ?
O2A C1A C2A C4A -164.00(11) . . . 3_667 ?
O1A C1A C2A C4A 15.72(16) . . . 3_667 ?
C4A C2A C3A C4A -0.16(19) 3_667 . . . ?
C1A C2A C3A C4A 179.58(10) . . . . ?
C2A C3A C4A C2A 0.16(19) . . . 3_667 ?
C3B N1B C1B N2B 0.05(15) . . . . ?
C2B N2B C1B N1B 0.12(14) . . . . ?
C1B N2B C2B C3B -0.25(14) . . . . ?
N2B C2B C3B N1B 0.28(14) . . . . ?
C1B N1B C3B C2B -0.21(14) . . . . ?
