#------------------------------------------------------------------------------
#$Date: 2023-05-30 11:05:43 +0300 (Tue, 30 May 2023) $
#$Revision: 284061 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/72/8107264.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_8107264
loop_
_publ_author_name
'Zhang, Tian'
'Li, Hua Bing'
_publ_section_title
;
 Crystal structure of
 poly[diaqua-(μ2-1H-benzo[d][1,2,3]triazole-5-carboxylato-κ2
 O:O&#x2032;)(\m2-oxalato-\k4O,O:O&#x2033;,O&#x2032;&#x2033;)europium(III)]
 monohydrate, C9H10N3O9Eu
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              961
_journal_page_last               963
_journal_paper_doi               10.1515/ncrs-2022-0336
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C9 H8 Eu N3 O8, H2 O'
_chemical_formula_sum            'C9 H10 Eu N3 O9'
_chemical_formula_weight         456.16
_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
_cell_angle_alpha                66.8554(8)
_cell_angle_beta                 72.9671(8)
_cell_angle_gamma                83.4968(9)
_cell_formula_units_Z            2
_cell_length_a                   7.9645(5)
_cell_length_b                   9.2934(6)
_cell_length_c                   10.0409(6)
_cell_measurement_reflns_used    2883
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.498
_cell_measurement_theta_min      2.292
_cell_volume                     653.41(7)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker SMART APEX diffractometer'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0104
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3996
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.292
_exptl_absorpt_coefficient_mu    4.855
_exptl_absorpt_correction_T_max  0.4924
_exptl_absorpt_correction_T_min  0.3766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.912
_refine_diff_density_min         -1.246
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2883
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0210
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0289P)²+1.0398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0519
_refine_ls_wR_factor_ref         0.0522
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2796
_reflns_number_total             2883
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0336_suppl.cif
_cod_data_source_block           eu
_cod_database_code               8107264
_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_max   0.492
_shelx_estimated_absorpt_t_min   0.377
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O1W-H1WA = O1W-H1WB = O2W-H2WA = O2W-H2WB = O3W-H3WA = O3W-H3WB
 0.84 with sigma of 0.01
 N3-H3
 0.88 with sigma of 0.01
 H1WA-H3WA
 2.2 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3A), C6(H6), C7(H7)
;
_olex2_submission_special_instructions 'No special instructions were received :'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Eu1 Eu 0.62212(2) 0.44800(2) 0.20524(2) 0.01333(6) Uani 1 1 d . . . . .
O1 O 0.4997(4) 0.2378(3) 0.2018(3) 0.0313(6) Uani 1 1 d . . . . .
O2 O 0.4358(4) 0.3431(3) -0.0165(3) 0.0330(6) Uani 1 1 d . . . . .
O3 O 0.8193(3) 0.4267(3) -0.0185(3) 0.0273(5) Uani 1 1 d . . . . .
O4 O 1.1013(3) 0.4404(3) -0.1486(3) 0.0289(6) Uani 1 1 d . . . . .
O5 O 0.6051(4) 0.6276(3) 0.3203(3) 0.0292(6) Uani 1 1 d . . . . .
O6 O 0.4915(4) 0.6718(3) 0.5323(3) 0.0294(6) Uani 1 1 d . . . . .
O1W O 0.8224(4) 0.2423(3) 0.2845(3) 0.0345(6) Uani 1 1 d D . . . .
H1WA H 0.796(7) 0.147(2) 0.317(6) 0.052 Uiso 1 1 d D U . . .
H1WB H 0.879(6) 0.247(6) 0.342(5) 0.052 Uiso 1 1 d D U . . .
O2W O 0.3135(4) 0.4993(4) 0.2690(3) 0.0350(6) Uani 1 1 d D . . . .
H2WA H 0.266(7) 0.530(6) 0.197(4) 0.052 Uiso 1 1 d D U . . .
H2WB H 0.233(5) 0.444(5) 0.343(4) 0.052 Uiso 1 1 d D U . . .
O3W O 0.6729(6) -0.0331(4) 0.3535(7) 0.0797(15) Uani 1 1 d D . . . .
H3WA H 0.569(2) 0.002(5) 0.366(10) 0.120 Uiso 1 1 d D U . . .
H3WB H 0.643(11) -0.127(4) 0.409(8) 0.120 Uiso 1 1 d D U . . .
N1 N 0.0391(5) -0.2174(4) 0.4779(4) 0.0343(7) Uani 1 1 d . . . . .
N2 N -0.0506(5) -0.3108(4) 0.4546(4) 0.0364(8) Uani 1 1 d . . . . .
N3 N -0.0168(5) -0.2722(4) 0.3052(4) 0.0325(7) Uani 1 1 d D . . . .
H3 H -0.068(6) -0.324(5) 0.269(5) 0.039 Uiso 1 1 d D U . . .
C1 C 0.4241(5) 0.2349(4) 0.1090(4) 0.0238(7) Uani 1 1 d . . . . .
C2 C 0.3124(5) 0.0958(4) 0.1529(4) 0.0250(7) Uani 1 1 d . . . . .
C3 C 0.2435(5) 0.0088(4) 0.3038(4) 0.0291(8) Uani 1 1 d . . . . .
H3A H 0.269456 0.031408 0.377970 0.035 Uiso 1 1 calc R U . . .
C4 C 0.1324(5) -0.1153(4) 0.3398(4) 0.0289(8) Uani 1 1 d . . . . .
C5 C 0.0973(5) -0.1505(4) 0.2276(4) 0.0288(8) Uani 1 1 d . . . . .
C6 C 0.1721(5) -0.0658(5) 0.0744(5) 0.0329(8) Uani 1 1 d . . . . .
H6 H 0.151679 -0.092300 0.000339 0.040 Uiso 1 1 calc R U . . .
C7 C 0.2770(5) 0.0582(5) 0.0393(4) 0.0303(8) Uani 1 1 d . . . . .
H7 H 0.326360 0.119359 -0.061320 0.036 Uiso 1 1 calc R U . . .
C8 C 0.9762(4) 0.4617(4) -0.0477(4) 0.0219(7) Uani 1 1 d . . . . .
C9 C 0.5281(4) 0.5863(4) 0.4567(4) 0.0223(7) Uani 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 Eu1 O3 79.97(9) . .
O1 Eu1 O4 140.67(10) . 2_765
O1 Eu1 O5 147.79(10) . .
O1 Eu1 O6 84.27(9) . 2_666
O1 Eu1 O1W 77.54(10) . .
O1 Eu1 O2W 76.55(11) . .
O1 Eu1 C8 122.24(9) . 2_765
O1 Eu1 C8 97.12(9) . .
O1 Eu1 C9 128.87(9) . .
O1 Eu1 C9 102.69(9) . 2_666
O2 Eu1 O1 106.00(10) 2_665 .
O2 Eu1 O3 75.20(10) 2_665 .
O2 Eu1 O4 88.36(10) 2_665 2_765
O2 Eu1 O5 83.95(10) 2_665 .
O2 Eu1 O6 137.84(10) 2_665 2_666
O2 Eu1 O1W 146.95(11) 2_665 .
O2 Eu1 O2W 71.55(10) 2_665 .
O2 Eu1 C8 80.92(10) 2_665 .
O2 Eu1 C8 86.64(10) 2_665 2_765
O2 Eu1 C9 99.33(10) 2_665 .
O2 Eu1 C9 121.86(10) 2_665 2_666
O3 Eu1 C8 20.49(9) . .
O3 Eu1 C8 48.53(8) . 2_765
O3 Eu1 C9 160.06(9) . 2_666
O3 Eu1 C9 150.31(9) . .
O4 Eu1 O3 68.41(8) 2_765 .
O4 Eu1 O1W 71.46(10) 2_765 .
O4 Eu1 O2W 142.42(10) 2_765 .
O4 Eu1 C8 20.26(8) 2_765 2_765
O4 Eu1 C8 48.29(8) 2_765 .
O4 Eu1 C9 82.42(9) 2_765 .
O4 Eu1 C9 99.86(9) 2_765 2_666
O5 Eu1 O3 132.13(9) . .
O5 Eu1 O4 68.39(9) . 2_765
O5 Eu1 O6 69.13(9) . 2_666
O5 Eu1 O1W 110.86(10) . .
O5 Eu1 O2W 77.93(10) . .
O5 Eu1 C8 114.84(9) . .
O5 Eu1 C8 88.30(9) . 2_765
O5 Eu1 C9 20.50(9) . .
O5 Eu1 C9 48.75(9) . 2_666
O6 Eu1 O3 146.60(9) 2_666 .
O6 Eu1 O4 109.55(10) 2_666 2_765
O6 Eu1 O1W 74.81(10) 2_666 .
O6 Eu1 O2W 71.48(10) 2_666 .
O6 Eu1 C8 139.42(9) 2_666 .
O6 Eu1 C8 122.81(9) 2_666 2_765
O6 Eu1 C9 20.65(9) 2_666 2_666
O6 Eu1 C9 48.90(9) 2_666 .
O1W Eu1 O3 73.13(10) . .
O1W Eu1 O2W 139.01(10) . .
O1W Eu1 C8 66.08(10) . .
O1W Eu1 C8 65.30(10) . 2_765
O1W Eu1 C9 88.02(10) . 2_666
O1W Eu1 C9 103.44(10) . .
O2W Eu1 O3 131.53(9) . .
O2W Eu1 C8 148.43(9) . .
O2W Eu1 C8 155.15(10) . 2_765
O2W Eu1 C9 67.58(9) . 2_666
O2W Eu1 C9 70.46(10) . .
C8 Eu1 C8 28.17(12) 2_765 .
C9 Eu1 C8 143.03(9) 2_666 .
C9 Eu1 C8 102.62(9) . 2_765
C9 Eu1 C8 117.72(9) 2_666 2_765
C9 Eu1 C8 130.69(9) . .
C9 Eu1 C9 28.35(12) . 2_666
C1 O1 Eu1 128.4(2) . .
C1 O2 Eu1 163.1(3) . 2_665
C8 O3 Eu1 117.1(2) . .
C8 O4 Eu1 119.2(2) . 2_765
C9 O5 Eu1 118.1(2) . .
C9 O6 Eu1 118.2(2) . 2_666
Eu1 O1W H1WA 122(4) . .
Eu1 O1W H1WB 118(4) . .
H1WA O1W H1WB 105(5) . .
Eu1 O2W H2WA 116(4) . .
Eu1 O2W H2WB 129(4) . .
H2WA O2W H2WB 102(5) . .
H3WA O3W H3WB 95(7) . .
N2 N1 C4 107.9(3) . .
N1 N2 N3 108.7(3) . .
N2 N3 H3 121(3) . .
N2 N3 C5 111.0(3) . .
C5 N3 H3 128(3) . .
O1 C1 Eu1 33.83(17) . .
O1 C1 C2 118.0(3) . .
O2 C1 Eu1 90.5(2) . .
O2 C1 O1 123.3(3) . .
O2 C1 C2 118.7(3) . .
C2 C1 Eu1 149.4(2) . .
C3 C2 C1 118.6(3) . .
C3 C2 C7 121.7(3) . .
C7 C2 C1 119.7(3) . .
C2 C3 H3A 121.7 . .
C2 C3 C4 116.7(3) . .
C4 C3 H3A 121.7 . .
N1 C4 C3 130.2(4) . .
N1 C4 C5 108.6(3) . .
C5 C4 C3 121.2(3) . .
N3 C5 C4 103.8(3) . .
N3 C5 C6 134.0(4) . .
C4 C5 C6 122.2(3) . .
C5 C6 H6 121.7 . .
C7 C6 C5 116.5(4) . .
C7 C6 H6 121.7 . .
C2 C7 H7 119.2 . .
C6 C7 C2 121.7(4) . .
C6 C7 H7 119.2 . .
Eu1 C8 Eu1 151.83(12) 2_765 .
O3 C8 Eu1 42.38(16) . .
O3 C8 Eu1 165.0(2) . 2_765
O3 C8 O4 126.1(3) . .
O3 C8 C8 117.8(4) . 2_765
O4 C8 Eu1 166.7(2) . .
O4 C8 Eu1 40.58(16) . 2_765
O4 C8 C8 116.1(4) . 2_765
C8 C8 Eu1 75.8(2) 2_765 .
C8 C8 Eu1 76.0(2) 2_765 2_765
Eu1 C9 Eu1 151.65(12) . 2_666
O5 C9 Eu1 166.4(2) . 2_666
O5 C9 Eu1 41.35(16) . .
O5 C9 O6 126.5(3) . .
O5 C9 C9 117.4(4) . 2_666
O6 C9 Eu1 166.6(2) . .
O6 C9 Eu1 41.16(16) . 2_666
O6 C9 C9 116.1(4) . 2_666
C9 C9 Eu1 76.4(2) 2_666 .
C9 C9 Eu1 75.3(2) 2_666 2_666
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Eu1 O1 2.296(3) .
Eu1 O2 2.234(3) 2_665
Eu1 O3 2.401(2) .
Eu1 O4 2.360(3) 2_765
Eu1 O5 2.347(2) .
Eu1 O6 2.351(3) 2_666
Eu1 O1W 2.385(3) .
Eu1 O2W 2.394(3) .
Eu1 C8 3.169(3) 2_765
Eu1 C8 3.170(3) .
Eu1 C9 3.133(3) .
Eu1 C9 3.148(3) 2_666
O1 C1 1.258(4) .
O2 C1 1.250(4) .
O3 C8 1.247(4) .
O4 C8 1.256(4) .
O5 C9 1.244(4) .
O6 C9 1.260(4) .
O1W H1WA 0.840(10) .
O1W H1WB 0.846(10) .
O2W H2WA 0.848(10) .
O2W H2WB 0.848(10) .
O3W H3WA 0.846(10) .
O3W H3WB 0.846(10) .
N1 N2 1.310(5) .
N1 C4 1.377(5) .
N2 N3 1.346(5) .
N3 H3 0.890(10) .
N3 C5 1.356(5) .
C1 C2 1.497(5) .
C2 C3 1.379(5) .
C2 C7 1.424(5) .
C3 H3A 0.9300 .
C3 C4 1.400(5) .
C4 C5 1.396(5) .
C5 C6 1.399(6) .
C6 H6 0.9300 .
C6 C7 1.369(5) .
C7 H7 0.9300 .
C8 C8 1.543(7) 2_765
C9 C9 1.538(7) 2_666
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1W H1WA O3W 0.840(10) 1.89(2) 2.695(5) 159(5) . yes
O1W H1WB N1 0.846(10) 2.007(18) 2.831(5) 164(5) 2_656 yes
O2W H2WA O3 0.848(10) 1.981(15) 2.820(4) 170(5) 2_665 yes
O2W H2WB N2 0.848(10) 2.118(13) 2.960(4) 172(5) 2_556 yes
O3W H3WA O1 0.846(10) 2.29(6) 2.826(5) 122(6) . yes
O3W H3WB O6 0.846(10) 2.07(3) 2.888(5) 161(8) 1_545 yes
N3 H3 O4 0.890(10) 2.001(19) 2.857(4) 161(4) 2_655 yes
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
Eu1 O1 C1 O2 15.7(5) . . . .
Eu1 O1 C1 C2 -163.3(2) . . . .
Eu1 O2 C1 Eu1 -94.4(9) 2_665 . . .
Eu1 O2 C1 O1 -103.1(9) 2_665 . . .
Eu1 O2 C1 C2 75.9(10) 2_665 . . .
Eu1 O3 C8 Eu1 -164.8(8) . . . 2_765
Eu1 O3 C8 O4 171.0(3) . . . .
Eu1 O3 C8 C8 -9.0(5) . . . 2_765
Eu1 O4 C8 Eu1 -162.1(9) 2_765 . . .
Eu1 O4 C8 O3 170.7(3) 2_765 . . .
Eu1 O4 C8 C8 -9.3(5) 2_765 . . 2_765
Eu1 O5 C9 Eu1 165.4(9) . . . 2_666
Eu1 O5 C9 O6 -172.3(3) . . . .
Eu1 O5 C9 C9 7.9(5) . . . 2_666
Eu1 O6 C9 Eu1 165.4(9) 2_666 . . .
Eu1 O6 C9 O5 -172.2(3) 2_666 . . .
Eu1 O6 C9 C9 7.6(5) 2_666 . . 2_666
Eu1 C1 C2 C3 5.6(7) . . . .
Eu1 C1 C2 C7 -175.7(3) . . . .
O1 C1 C2 C3 23.9(5) . . . .
O1 C1 C2 C7 -157.3(3) . . . .
O2 C1 C2 C3 -155.1(4) . . . .
O2 C1 C2 C7 23.6(5) . . . .
N1 N2 N3 C5 -0.1(5) . . . .
N1 C4 C5 N3 0.3(4) . . . .
N1 C4 C5 C6 179.5(4) . . . .
N2 N1 C4 C3 178.1(4) . . . .
N2 N1 C4 C5 -0.4(5) . . . .
N2 N3 C5 C4 -0.1(4) . . . .
N2 N3 C5 C6 -179.1(4) . . . .
N3 C5 C6 C7 176.4(4) . . . .
C1 C2 C3 C4 176.8(3) . . . .
C1 C2 C7 C6 -178.4(4) . . . .
C2 C3 C4 N1 -176.9(4) . . . .
C2 C3 C4 C5 1.4(6) . . . .
C3 C2 C7 C6 0.3(6) . . . .
C3 C4 C5 N3 -178.3(4) . . . .
C3 C4 C5 C6 0.8(6) . . . .
C4 N1 N2 N3 0.3(5) . . . .
C4 C5 C6 C7 -2.5(6) . . . .
C5 C6 C7 C2 1.9(6) . . . .
C7 C2 C3 C4 -2.0(6) . . . .
