#------------------------------------------------------------------------------
#$Date: 2020-01-31 07:51:43 +0200 (Fri, 31 Jan 2020) $
#$Revision: 247406 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/19/2021966.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_2021966
loop_
_publ_author_name
'Zheng, Wenxu'
'Wu, Kechen'
_publ_section_title
;
 Anion-directed assemblies of europium(III) coordination polymers based on
 1H-benzimidazole-5,6-dicarboxylate: structures and luminescence
 properties
;
_journal_coeditor_code           JX3052
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229620000637
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          '[Eu2 (C9 H4 N2 O4)2 (C2 O4) (H2 O)2], 2H2 O'
_chemical_formula_moiety         'C20 H12 Eu2 N4 O14, 2(H2 O)'
_chemical_formula_sum            'C20 H16 Eu2 N4 O16'
_chemical_formula_weight         872.28
_chemical_name_systematic
'Poly[[diaquabis(μ₄-1H-benzimidazole-5,6-dicarboxylato-κ⁶N³:O⁵,O^5'^:O⁵,O⁶:O^6'^)(μ₂-oxalato-κ⁴O¹,O²:O^1'^,O^2'^)dieuropium(III)] dihydrate]'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                117.97(3)
_cell_angle_beta                 93.19(3)
_cell_angle_gamma                99.12(3)
_cell_formula_units_Z            1
_cell_length_a                   7.4900(15)
_cell_length_b                   9.4200(19)
_cell_length_c                   9.6533(19)
_cell_measurement_reflns_used    696
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4449
_cell_measurement_theta_min      2.4185
_cell_volume                     587.3(3)
_computing_cell_refinement
;
CrystalClear (Rigaku OD, 2005)
;
_computing_data_collection
;
CrystalClear (Rigaku OD, 2005)
;
_computing_data_reduction
;
CrystalClear (Rigaku OD, 2005)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2015)
;
_computing_structure_solution
;
olex2.solve (Bourhis et al.,  2015)
;
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Mercury2 (2x2 bin mode)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4544
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.427
_diffrn_reflns_theta_min         2.504
_diffrn_source                   'Sealed Tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.387
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrystalClear; Rigaku OD, 2005)
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    2.466
_exptl_crystal_description       block
_exptl_crystal_F_000             418
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         2.173
_refine_diff_density_min         -1.977
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2669
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0387
_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)+(0.0284P)²+1.6056P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0795
_reflns_number_gt                2403
_reflns_number_total             2669
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jx3052sup1.cif
_cod_data_source_block           1
_cod_database_code               2021966
_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_estimated_absorpt_t_min   0.412
_shelx_estimated_absorpt_t_max   0.499
_shelxl_version_number           20.13
loop_
_space_group_symop_operation_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
Eu Eu1 0.12225(4) 0.34001(3) 0.31736(3) 0.01315(11) Uani d 1
O O1 -0.0767(5) 0.1837(5) 0.0597(5) 0.0189(9) Uani d 1
C C7 0.4084(7) 0.3471(7) -0.2893(7) 0.0134(11) Uani d 1
C C2 -0.0549(7) 0.0403(7) -0.0355(7) 0.0135(11) Uani d 1
O O3 -0.0414(6) 0.4683(5) -0.2261(5) 0.0195(9) Uani d 1
O O2 -0.1136(6) -0.0382(5) -0.1801(5) 0.0201(9) Uani d 1
O O1W -0.1517(7) 0.2013(5) 0.3770(6) 0.0272(11) Uani d 1
H H1WA -0.222(8) 0.266(7) 0.423(8) 0.041 Uiso d 1
H H1WB -0.163(10) 0.133(7) 0.412(8) 0.041 Uiso d 1
O O4 0.1354(5) 0.4942(5) -0.3894(5) 0.0180(9) Uani d 1
O O6 0.6220(5) 0.4190(5) -0.4316(5) 0.0196(9) Uani d 1
O O5 0.3463(5) 0.2691(5) -0.5621(5) 0.0160(8) Uani d 1
N N2 0.5840(7) 0.2290(6) 0.0010(6) 0.0192(11) Uani d 1
H H2 0.692(10) 0.202(8) -0.011(8) 0.029 Uiso d 1
C C9 0.4628(8) 0.3513(7) -0.4363(7) 0.0145(12) Uani d 1
C C1 0.4795(8) 0.2333(7) 0.1134(7) 0.0195(13) Uani d 1
H H1 0.5147 0.2079 0.1916 0.023 Uiso calc 1
C C3 0.1984(8) 0.3534(7) -0.1001(7) 0.0162(12) Uani d 1
H H3 0.0885 0.3712 -0.0614 0.019 Uiso calc 1
N N1 0.3234(7) 0.2772(6) 0.1004(6) 0.0164(10) Uani d 1
C C6 0.3242(8) 0.3039(7) -0.0316(7) 0.0138(11) Uani d 1
C C10 0.1033(7) 0.4467(6) -0.2863(7) 0.0128(11) Uani d 1
C C4 0.5347(8) 0.2975(7) -0.2195(7) 0.0168(12) Uani d 1
H H4 0.6460 0.2810 -0.2559 0.020 Uiso calc 1
C C5 0.4889(8) 0.2735(7) -0.0939(7) 0.0140(11) Uani d 1
C C8 0.2391(8) 0.3765(7) -0.2294(7) 0.0136(11) Uani d 1
O O2W 0.8217(11) 0.0418(8) 0.5565(8) 0.0605(18) Uani d 1
H H2WA 0.872(13) 0.091(11) 0.652(4) 0.091 Uiso d 1
H H2WB 0.750(12) -0.044(7) 0.543(11) 0.091 Uiso 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'
Eu Eu -0.1578 3.6682 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O1 Eu1 C2 . . 20.06(13)
O1 Eu1 C2 . 2 46.83(13)
O1 Eu1 O3 . 2_565 70.28(13)
O1 Eu1 O2 . 2 65.52(13)
O1 Eu1 O1W . . 76.81(15)
O1 Eu1 O4 . 1_556 145.90(13)
O1 Eu1 O4 . 2_565 82.28(13)
O1 Eu1 O6 . 2_665 133.81(14)
O1 Eu1 N1 . . 71.86(15)
O1 Eu1 C10 . 2_565 71.66(14)
C2 Eu1 C2 . 2 27.19(19)
O3 Eu1 C2 2_565 . 87.50(14)
O3 Eu1 C2 2_565 2 113.71(14)
O3 Eu1 O2 2_565 2 133.56(14)
O3 Eu1 O1W 2_565 . 111.46(15)
O3 Eu1 O4 2_565 1_556 104.18(13)
O3 Eu1 O4 2_565 2_565 50.97(12)
O3 Eu1 N1 2_565 . 81.74(14)
O3 Eu1 C10 2_565 2_565 25.25(14)
O2 Eu1 C2 2 . 46.62(13)
O2 Eu1 C2 2 2 19.86(13)
O2 Eu1 O4 2 2_565 131.93(14)
O2 Eu1 N1 2 . 71.89(15)
O2 Eu1 C10 2 2_565 135.58(15)
O1W Eu1 C2 . . 78.76(15)
O1W Eu1 C2 . 2 76.60(14)
O1W Eu1 O2 . 2 71.75(14)
O1W Eu1 O4 . 2_565 66.60(14)
O1W Eu1 N1 . . 139.25(16)
O1W Eu1 C10 . 2_565 87.91(15)
O4 Eu1 C2 2_565 2 122.92(14)
O4 Eu1 C2 1_556 . 152.96(13)
O4 Eu1 C2 2_565 . 101.26(14)
O4 Eu1 C2 1_556 2 138.51(13)
O4 Eu1 O2 1_556 2 120.25(13)
O4 Eu1 O1W 1_556 . 74.28(15)
O4 Eu1 O4 1_556 2_565 69.91(15)
O4 Eu1 N1 1_556 . 141.95(15)
O4 Eu1 C10 1_556 2_565 89.49(14)
O4 Eu1 C10 2_565 2_565 26.10(13)
O6 Eu1 C2 2_665 2 135.80(13)
O6 Eu1 C2 2_665 . 136.64(13)
O6 Eu1 O3 2_665 2_565 73.19(14)
O6 Eu1 O2 2_665 2 132.08(14)
O6 Eu1 O1W 2_665 . 144.30(14)
O6 Eu1 O4 2_665 2_565 95.99(13)
O6 Eu1 O4 2_665 1_556 70.39(14)
O6 Eu1 N1 2_665 . 75.83(15)
O6 Eu1 C10 2_665 2_565 86.76(14)
O5 Eu1 O1 1_556 . 131.67(13)
O5 Eu1 C2 1_556 2 84.95(14)
O5 Eu1 C2 1_556 . 111.65(14)
O5 Eu1 O3 1_556 2_565 147.90(14)
O5 Eu1 O2 1_556 2 67.25(14)
O5 Eu1 O1W 1_556 . 97.83(15)
O5 Eu1 O4 1_556 2_565 140.17(13)
O5 Eu1 O4 1_556 1_556 70.60(13)
O5 Eu1 O6 1_556 2_665 75.36(14)
O5 Eu1 N1 1_556 . 84.53(14)
O5 Eu1 C10 1_556 2_565 156.66(15)
N1 Eu1 C2 . . 62.99(15)
N1 Eu1 C2 . 2 63.03(15)
N1 Eu1 O4 . 2_565 131.76(13)
N1 Eu1 C10 . 2_565 105.79(15)
C10 Eu1 C2 2_565 2 118.38(15)
C10 Eu1 C2 2_565 . 91.63(15)
C2 O1 Eu1 . . 118.4(4)
C4 C7 C9 . . 113.2(5)
C4 C7 C8 . . 120.7(5)
C8 C7 C9 . . 125.9(5)
Eu1 C2 Eu1 . 2 152.81(19)
O1 C2 Eu1 . . 41.5(3)
O1 C2 Eu1 . 2 163.4(4)
O1 C2 C2 . 2 116.5(6)
C2 C2 Eu1 2 . 76.4(4)
C2 C2 Eu1 2 2 76.4(4)
O2 C2 Eu1 . 2 43.0(3)
O2 C2 Eu1 . . 162.0(4)
O2 C2 O1 . . 125.7(5)
O2 C2 C2 . 2 117.8(6)
C10 O3 Eu1 . 2_565 97.3(3)
C2 O2 Eu1 . 2 117.2(3)
Eu1 O1W H1WA . . 112(4)
Eu1 O1W H1WB . . 131(5)
H1WA O1W H1WB . . 105.8(17)
Eu1 O4 Eu1 1_554 2_565 110.09(15)
C10 O4 Eu1 . 1_554 132.2(4)
C10 O4 Eu1 . 2_565 91.5(3)
C9 O6 Eu1 . 2_665 151.5(4)
C9 O5 Eu1 . 1_554 133.0(3)
C1 N2 H2 . . 127(5)
C1 N2 C5 . . 107.1(5)
C5 N2 H2 . . 126(5)
O6 C9 C7 . . 119.0(5)
O6 C9 O5 . . 124.2(5)
O5 C9 C7 . . 116.4(5)
N2 C1 H1 . . 123.3
N1 C1 N2 . . 113.4(5)
N1 C1 H1 . . 123.3
C6 C3 H3 . . 120.6
C6 C3 C8 . . 118.9(5)
C8 C3 H3 . . 120.6
C1 N1 Eu1 . . 120.6(4)
C1 N1 C6 . . 105.0(5)
C6 N1 Eu1 . . 133.5(3)
C3 C6 N1 . . 131.2(5)
C3 C6 C5 . . 120.0(5)
N1 C6 C5 . . 108.8(5)
O3 C10 Eu1 . 2_565 57.4(3)
O3 C10 O4 . . 118.5(5)
O3 C10 C8 . . 119.6(5)
O4 C10 Eu1 . 2_565 62.4(3)
O4 C10 C8 . . 121.8(5)
C8 C10 Eu1 . 2_565 165.0(4)
C7 C4 H4 . . 121.2
C5 C4 C7 . . 117.6(5)
C5 C4 H4 . . 121.2
N2 C5 C6 . . 105.7(5)
N2 C5 C4 . . 131.6(5)
C4 C5 C6 . . 122.6(5)
C7 C8 C10 . . 124.3(5)
C3 C8 C7 . . 120.2(5)
C3 C8 C10 . . 115.3(5)
H2WA O2W H2WB . . 105.8(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Eu1 O1 . 2.456(4)
Eu1 C2 . 3.259(6)
Eu1 C2 2 3.260(6)
Eu1 O3 2_565 2.486(4)
Eu1 O2 2 2.498(4)
Eu1 O1W . 2.497(4)
Eu1 O4 2_565 2.595(4)
Eu1 O4 1_556 2.489(4)
Eu1 O6 2_665 2.465(4)
Eu1 O5 1_556 2.342(4)
Eu1 N1 . 2.545(5)
Eu1 C10 2_565 2.926(5)
O1 C2 . 1.272(7)
C7 C9 . 1.514(7)
C7 C4 . 1.390(8)
C7 C8 . 1.436(7)
C2 Eu1 2 3.260(6)
C2 C2 2 1.532(11)
C2 O2 . 1.244(7)
O3 Eu1 2_565 2.486(4)
O3 C10 . 1.259(7)
O2 Eu1 2 2.498(4)
O1W H1WA . 0.846(10)
O1W H1WB . 0.847(10)
O4 Eu1 2_565 2.595(4)
O4 Eu1 1_554 2.489(4)
O4 C10 . 1.288(7)
O6 Eu1 2_665 2.465(4)
O6 C9 . 1.248(7)
O5 Eu1 1_554 2.342(4)
O5 C9 . 1.274(7)
N2 H2 . 0.88(7)
N2 C1 . 1.361(7)
N2 C5 . 1.381(7)
C1 H1 . 0.9300
C1 N1 . 1.318(8)
C3 H3 . 0.9300
C3 C6 . 1.380(8)
C3 C8 . 1.404(8)
N1 C6 . 1.410(7)
C6 C5 . 1.413(8)
C10 Eu1 2_565 2.926(5)
C10 C8 . 1.506(8)
C4 H4 . 0.9300
C4 C5 . 1.385(8)
O2W H2WA . 0.848(10)
O2W H2WB . 0.847(10)
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
O1W H1WA O6 1_456 0.846(10) 2.058(17) 2.896(6) 170(6)
O1W H1WB O2W 1_455 0.847(10) 1.96(3) 2.771(7) 161(7)
N2 H2 O1 1_655 0.88(7) 1.89(7) 2.715(6) 155(7)
O2W H2WA O2 1_656 0.848(10) 2.44(8) 3.008(7) 125(8)
O2W H2WB O5 2_655 0.847(10) 2.22(4) 3.025(7) 159(9)
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_site_symmetry_4
_geom_torsion
Eu1 O1 C2 Eu1 . 2 155.2(11)
Eu1 O1 C2 C2 . 2 16.5(7)
Eu1 O1 C2 O2 . . -162.9(4)
Eu1 C2 O2 Eu1 . 2 157.0(10)
Eu1 O3 C10 O4 2_565 . -13.4(5)
Eu1 O3 C10 C8 2_565 . 162.8(4)
Eu1 O4 C10 Eu1 1_554 2_565 -119.2(4)
Eu1 O4 C10 O3 2_565 . 12.8(5)
Eu1 O4 C10 O3 1_554 . -106.4(5)
Eu1 O4 C10 C8 2_565 . -163.4(5)
Eu1 O4 C10 C8 1_554 . 77.5(7)
Eu1 O6 C9 C7 2_665 . -58.0(10)
Eu1 O6 C9 O5 2_665 . 129.9(7)
Eu1 O5 C9 C7 1_554 . 96.1(5)
Eu1 O5 C9 O6 1_554 . -91.6(6)
Eu1 N1 C6 C3 . . -10.5(10)
Eu1 N1 C6 C5 . . 168.5(4)
Eu1 C10 C8 C7 2_565 . -105.7(14)
Eu1 C10 C8 C3 2_565 . 68.8(15)
O1 C2 O2 Eu1 . 2 -163.8(4)
C7 C4 C5 N2 . . -178.3(6)
C7 C4 C5 C6 . . -2.6(9)
C2 C2 O2 Eu1 2 2 16.8(7)
O3 C10 C8 C7 . . -179.8(5)
O3 C10 C8 C3 . . -5.4(8)
O4 C10 C8 C7 . . -3.7(9)
O4 C10 C8 C3 . . 170.7(5)
N2 C1 N1 Eu1 . . -170.3(4)
N2 C1 N1 C6 . . 0.1(7)
C9 C7 C4 C5 . . -173.6(5)
C9 C7 C8 C3 . . 173.9(5)
C9 C7 C8 C10 . . -11.9(9)
C1 N2 C5 C6 . . 0.0(6)
C1 N2 C5 C4 . . 176.2(6)
C1 N1 C6 C3 . . -179.1(6)
C1 N1 C6 C5 . . -0.1(6)
C3 C6 C5 N2 . . 179.2(5)
C3 C6 C5 C4 . . 2.6(9)
N1 C6 C5 N2 . . 0.1(6)
N1 C6 C5 C4 . . -176.6(5)
C6 C3 C8 C7 . . 0.6(8)
C6 C3 C8 C10 . . -174.1(5)
C4 C7 C9 O6 . . -47.3(7)
C4 C7 C9 O5 . . 125.4(5)
C4 C7 C8 C3 . . -0.7(8)
C4 C7 C8 C10 . . 173.5(5)
C5 N2 C1 N1 . . -0.1(7)
C8 C7 C9 O6 . . 137.7(6)
C8 C7 C9 O5 . . -49.6(8)
C8 C7 C4 C5 . . 1.7(8)
C8 C3 C6 N1 . . 177.4(6)
C8 C3 C6 C5 . . -1.5(9)

_cod_database_fobs_code 2021966
