#------------------------------------------------------------------------------
#$Date: 2021-07-16 07:34:01 +0300 (Fri, 16 Jul 2021) $
#$Revision: 267580 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/32/7243209.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_7243209
loop_
_publ_author_name
'Theppitak, Chatphorn'
'Kielar, Filip'
'Dungkaew, Winya'
'Sukwattanasinitt, Mongkol'
'Kangkaew, Laongdao'
'Sahasithiwat, Somboon'
'Zenno, Hikaru'
'Hayami, Shinya'
'Chainok, Kittipong'
_publ_section_title
;
 The coordination chemistry of benzhydrazide with lanthanide(iii) ions:
 hydrothermal in situ ligand formation, structures, magnetic and
 photoluminescence sensing properties
;
_journal_issue                   40
_journal_name_full               'RSC Advances'
_journal_page_first              24709
_journal_page_last               24721
_journal_paper_doi               10.1039/D1RA03106F
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C28 H32 Eu N9 O7, 3(N O3)'
_chemical_formula_sum            'C28 H32 Eu N12 O16'
_chemical_formula_weight         944.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-02-21 deposited with the CCDC.	2021-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.1570(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.7339(8)
_cell_length_b                   15.3481(6)
_cell_length_c                   10.4654(4)
_cell_measurement_reflns_used    3923
_cell_measurement_temperature    296
_cell_measurement_theta_max      23.312
_cell_measurement_theta_min      2.405
_cell_volume                     3910.6(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.0
_diffrn_detector                 'Bruker PHOTON 200 area detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_detector_type            'PHOTON II area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'BRUKER D8 QUEST CMOS PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.1243
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            39760
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.117
_diffrn_reflns_theta_min         2.405
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_type              Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.687
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0885 before and 0.0769 after correction. The Ratio of minimum to maximum transmission is 0.8727. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_description       block
_exptl_crystal_F_000             1900
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.731
_refine_diff_density_min         -1.598
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         4338
_refine_ls_number_restraints     325
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0460
_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)+(0.0458P)²+15.7775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1274
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2953
_reflns_number_total             4338
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra03106f2.cif
_cod_data_source_block           2eu
_cod_database_code               7243209
_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_estimated_absorpt_t_max   0.751
_shelx_estimated_absorpt_t_min   0.668
_olex2_refinement_description
;
1. Restrained distances
 N4-H4 = N2-H2
 0.86 with sigma of 0.01
 N3-H3A = N3-H3B = N1-H1B = N1-H1A
 0.89 with sigma of 0.01
 N5-O3 \\sim N5-O5 \\sim N5-O4
 with sigma of 0.02
 O10-O11 \\sim O10-O9
 with sigma of 0.01
 O11-O9 \\sim O11-O10
 with sigma of 0.01
 N7-O9 \\sim N7-O10 \\sim N7-O11
 with sigma of 0.02
 O9-O10 \\sim O9-O11
 with sigma of 0.01
 C2-C3 \\sim C2A-C3A
 with sigma of 0.02
 C2-C4 \\sim C2A-C4A
 with sigma of 0.04
 C2-C7 \\sim C2A-C7A
 with sigma of 0.02
 C3-C4 \\sim C3A-C4A
 with sigma of 0.02
 C3-C5 \\sim C3A-C5A
 with sigma of 0.04
 C2-C6 \\sim C2A-C6A
 with sigma of 0.04
 C3-C7 \\sim C3A-C7A
 with sigma of 0.04
 C4-C6 \\sim C4A-C6A
 with sigma of 0.04
 C5-C7 \\sim C5A-C7A
 with sigma of 0.04
 C4-C5 \\sim C4A-C5A
 with sigma of 0.02
 C1-C2 \\sim C1-C2A
 with sigma of 0.02
 C5-C6 \\sim C5A-C6A
 with sigma of 0.02
 C6-C7 \\sim C6A-C7A
 with sigma of 0.02
 C1-C3 \\sim C1-C3A
 with sigma of 0.04
 C1-C7 \\sim C1-C7A
 with sigma of 0.04
 O6-O7 \\sim O6A-O7A
 with sigma of 0.04
 O8-N6 \\sim O8A-N6A
 with sigma of 0.02
 O6-O8 \\sim O6A-O8A
 with sigma of 0.04
 O7-O8 \\sim O7A-O8A
 with sigma of 0.04
 O7-N6 \\sim O7A-N6A
 with sigma of 0.02
 O6-N6 \\sim O6A-N6A
 with sigma of 0.02
2. Restrained planarity
 O9, O10, O11, N7
 with sigma of 0.1
3. Uiso/Uaniso restraints and constraints
Uanis(N7) \\sim Ueq, Uanis(O9) \\sim Ueq, Uanis(O10) \\sim Ueq, Uanis(O11)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C2A) \\sim Ueq, Uanis(C7A) \\sim Ueq, Uanis(C6A) \\sim Ueq, Uanis(C5A)
\\sim Ueq, Uanis(C4A) \\sim Ueq, Uanis(C3A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim
Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N6) \\sim Ueq, Uanis(O6) \\sim Ueq, Uanis(O7) \\sim Ueq, Uanis(O8) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N6A) \\sim Ueq, Uanis(O6A) \\sim Ueq, Uanis(O7A) \\sim Ueq, Uanis(O8A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 O9, O10, O11, N7
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C1, C2, C3, C4, C5, C6, C7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C1, C2A, C3A, C4A, C5A, C6A, C7A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O6, O7, O8, N6
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O6A, O7A, O8A, N6A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(C2A)=Sof(C3A)=Sof(H3AA)=Sof(C4A)=Sof(H4AA)=Sof(C5A)=Sof(H5A)=Sof(C6A)=
 Sof(H6A)=Sof(C7A)=Sof(H7A)=1-FVAR(1)
 Sof(C2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4A)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=
 Sof(C7)=Sof(H7)=FVAR(1)
 Sof(O6A)=Sof(O7A)=Sof(O8A)=Sof(N6A)=1-FVAR(2)
 Sof(O6)=Sof(O7)=Sof(O8)=Sof(N6)=FVAR(2)
 Fixed Sof: O3(0.5) O4(0.5) O5(0.5) O9(0.5) O10(0.5) O11(0.5) N5(0.5) N7(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C3A(H3AA), C4(H4A), C4A(H4AA), C5(H5), C5A(H5A), C6(H6), C6A(H6A),
 C7(H7), C7A(H7A), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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 0.500000 0.32093(3) 0.750000 0.05429(17) Uani 1 2 d S T P . .
O1 O 0.50919(16) 0.2242(3) 0.5774(4) 0.0580(10) Uani 1 1 d . . . . .
O2 O 0.41299(15) 0.2471(3) 0.6966(4) 0.0589(10) Uani 1 1 d . . . . .
O3 O 0.5052(3) 0.4796(5) 0.6906(7) 0.0513(19) Uani 0.5 1 d D . P A -1
O4 O 0.5133(4) 0.6191(5) 0.7089(8) 0.062(2) Uani 0.5 1 d D . P A -1
O5 O 0.4968(3) 0.5426(5) 0.8727(8) 0.0553(19) Uani 0.5 1 d D . P A -1
O6 O 0.3605(9) 0.3530(6) 0.2327(12) 0.078(4) Uani 0.64(4) 1 d D U P B 1
O6A O 0.3365(13) 0.375(2) 0.254(2) 0.079(6) Uani 0.36(4) 1 d D U P B 2
O7 O 0.3558(7) 0.4800(10) 0.3126(14) 0.079(3) Uani 0.64(4) 1 d D U P B 1
O7A O 0.3530(15) 0.509(2) 0.282(3) 0.092(7) Uani 0.36(4) 1 d D U P B 2
O8 O 0.3761(13) 0.4652(13) 0.1227(18) 0.085(6) Uani 0.64(4) 1 d D U P B 1
O8A O 0.368(2) 0.4489(19) 0.107(3) 0.069(6) Uani 0.36(4) 1 d D U P B 2
O9 O 0.6912(7) 0.3133(11) 0.5341(18) 0.179(5) Uani 0.5 1 d D U P C -1
O10 O 0.7361(8) 0.1692(13) 0.518(3) 0.224(7) Uani 0.5 1 d D U P C -1
O11 O 0.7915(8) 0.3071(13) 0.530(3) 0.223(7) Uani 0.5 1 d D U P C -1
N1 N 0.5634(2) 0.3732(4) 0.5917(8) 0.0830(19) Uani 1 1 d D . . . .
H1A H 0.548(3) 0.415(3) 0.538(5) 0.08(2) Uiso 1 1 d D . . . .
H1B H 0.5935(17) 0.394(4) 0.641(5) 0.08(2) Uiso 1 1 d D . . . .
N2 N 0.5762(2) 0.3034(4) 0.5144(8) 0.0814(19) Uani 1 1 d D . . . .
H2 H 0.593(4) 0.315(6) 0.452(7) 0.15(5) Uiso 1 1 d D . . . .
N3 N 0.4300(2) 0.3798(3) 0.5501(6) 0.0614(14) Uani 1 1 d D . . . .
H3A H 0.414(2) 0.430(2) 0.568(5) 0.051(16) Uiso 1 1 d D . . . .
H3B H 0.445(3) 0.388(5) 0.479(4) 0.09(3) Uiso 1 1 d D . . . .
N4 N 0.38564(19) 0.3218(3) 0.5133(5) 0.0551(12) Uani 1 1 d D . . . .
H4 H 0.364(2) 0.329(4) 0.440(3) 0.08(2) Uiso 1 1 d D . . . .
N5 N 0.498(3) 0.5483(5) 0.753(2) 0.049(3) Uani 0.5 1 d D . P A -1
N6 N 0.3629(8) 0.4337(7) 0.2217(13) 0.054(3) Uani 0.64(4) 1 d D U P B 1
N6A N 0.356(2) 0.4438(16) 0.217(3) 0.072(7) Uani 0.36(4) 1 d D U P B 2
N7 N 0.7402(7) 0.2631(11) 0.5362(19) 0.196(5) Uani 0.5 1 d D U P C -1
C1 C 0.5458(2) 0.2319(4) 0.5105(7) 0.0644(14) Uani 1 1 d D . . . .
C2 C 0.558(2) 0.1553(9) 0.430(3) 0.073(4) Uani 0.53(3) 1 d D U P D 1
C2A C 0.560(2) 0.1650(9) 0.424(3) 0.067(4) Uani 0.47(3) 1 d D U P D 2
C3 C 0.5421(9) 0.0718(9) 0.4619(16) 0.079(4) Uani 0.53(3) 1 d D U P D 1
H3 H 0.523104 0.065313 0.530422 0.095 Uiso 0.53(3) 1 calc R U P D 1
C3A C 0.5668(10) 0.0816(10) 0.4739(17) 0.077(4) Uani 0.47(3) 1 d D U P D 2
H3AA H 0.561016 0.069174 0.557449 0.093 Uiso 0.47(3) 1 calc R U P D 2
C4 C 0.5538(10) -0.0017(11) 0.3945(16) 0.096(4) Uani 0.53(3) 1 d D U P D 1
H4A H 0.545339 -0.056641 0.422813 0.115 Uiso 0.53(3) 1 calc R U P D 1
C4A C 0.5825(11) 0.0169(12) 0.3947(16) 0.087(5) Uani 0.47(3) 1 d D U P D 2
H4AA H 0.583895 -0.041170 0.420314 0.105 Uiso 0.47(3) 1 calc R U P D 2
C5 C 0.5775(9) 0.0061(15) 0.2880(17) 0.099(5) Uani 0.53(3) 1 d D U P D 1
H5 H 0.584808 -0.043219 0.242475 0.119 Uiso 0.53(3) 1 calc R U P D 1
C5A C 0.5956(10) 0.0408(16) 0.2784(17) 0.087(5) Uani 0.47(3) 1 d D U P D 2
H5A H 0.611269 -0.000584 0.231131 0.104 Uiso 0.47(3) 1 calc R U P D 2
C6 C 0.5906(10) 0.0878(16) 0.247(2) 0.102(5) Uani 0.53(3) 1 d D U P D 1
H6 H 0.606403 0.093715 0.173197 0.123 Uiso 0.53(3) 1 calc R U P D 1
C6A C 0.5868(9) 0.1239(15) 0.2277(18) 0.088(4) Uani 0.47(3) 1 d D U P D 2
H6A H 0.591227 0.135420 0.142923 0.106 Uiso 0.47(3) 1 calc R U P D 2
C7 C 0.5803(10) 0.1605(14) 0.3162(18) 0.093(4) Uani 0.53(3) 1 d D U P D 1
H7 H 0.588516 0.215101 0.286117 0.111 Uiso 0.53(3) 1 calc R U P D 1
C7A C 0.5716(10) 0.1881(12) 0.3023(17) 0.081(4) Uani 0.47(3) 1 d D U P D 2
H7A H 0.568791 0.245579 0.273729 0.097 Uiso 0.47(3) 1 calc R U P D 2
C8 C 0.3800(2) 0.2572(4) 0.5931(6) 0.0481(13) Uani 1 1 d . . . . .
C9 C 0.3326(2) 0.1972(3) 0.5575(6) 0.0523(14) Uani 1 1 d . . . . .
C10 C 0.3039(3) 0.1890(4) 0.4329(7) 0.0703(18) Uani 1 1 d . . . . .
H10 H 0.313290 0.222858 0.366385 0.084 Uiso 1 1 calc R U . . .
C11 C 0.2613(3) 0.1304(5) 0.4071(9) 0.087(2) Uani 1 1 d . . . . .
H11 H 0.242628 0.124039 0.322340 0.104 Uiso 1 1 calc R U . . .
C12 C 0.2458(3) 0.0818(5) 0.5028(11) 0.096(3) Uani 1 1 d . . . . .
H12 H 0.216743 0.042780 0.483580 0.115 Uiso 1 1 calc R U . . .
C13 C 0.2735(3) 0.0905(5) 0.6286(10) 0.093(3) Uani 1 1 d . . . . .
H13 H 0.263085 0.057473 0.694809 0.112 Uiso 1 1 calc R U . . .
C14 C 0.3167(3) 0.1483(4) 0.6559(8) 0.0681(18) Uani 1 1 d . . . . .
H14 H 0.335224 0.154556 0.740761 0.082 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Eu1 O1 102.78(19) . 2_656 ?
O1 Eu1 O2 74.41(14) . . ?
O1 Eu1 O2 71.42(13) 2_656 . ?
O1 Eu1 O2 71.43(13) . 2_656 ?
O1 Eu1 O2 74.41(14) 2_656 2_656 ?
O1 Eu1 O3 113.55(19) . . ?
O1 Eu1 O3 143.66(19) 2_656 . ?
O1 Eu1 N1 63.91(19) . . ?
O1 Eu1 N1 145.57(17) 2_656 . ?
O1 Eu1 N1 145.57(17) . 2_656 ?
O1 Eu1 N1 63.91(19) 2_656 2_656 ?
O1 Eu1 N3 132.90(15) . 2_656 ?
O1 Eu1 N3 75.43(17) . . ?
O1 Eu1 N3 75.43(17) 2_656 2_656 ?
O1 Eu1 N3 132.90(15) 2_656 . ?
O2 Eu1 O2 123.9(2) . 2_656 ?
O2 Eu1 O3 115.4(2) 2_656 . ?
O2 Eu1 O3 118.7(2) . . ?
O2 Eu1 N1 71.24(18) 2_656 . ?
O2 Eu1 N1 71.24(18) . 2_656 ?
O2 Eu1 N1 127.7(2) . . ?
O2 Eu1 N1 127.7(2) 2_656 2_656 ?
O2 Eu1 N3 62.70(14) . . ?
O2 Eu1 N3 62.70(14) 2_656 2_656 ?
O2 Eu1 N3 141.46(17) . 2_656 ?
O2 Eu1 N3 141.46(17) 2_656 . ?
O3 Eu1 N1 58.8(2) . . ?
O3 Eu1 N1 85.5(2) . 2_656 ?
O3 Eu1 N3 61.8(2) . . ?
O3 Eu1 N3 79.0(2) . 2_656 ?
N1 Eu1 N1 144.1(3) 2_656 . ?
N1 Eu1 N3 90.8(2) 2_656 . ?
N1 Eu1 N3 76.9(2) . . ?
N1 Eu1 N3 76.9(2) 2_656 2_656 ?
N1 Eu1 N3 90.8(2) . 2_656 ?
N3 Eu1 N3 139.8(2) . 2_656 ?
C1 O1 Eu1 123.0(4) . . ?
C8 O2 Eu1 124.4(3) . . ?
N5 O3 Eu1 131.3(8) . . ?
Eu1 N1 H1A 112(5) . . ?
Eu1 N1 H1B 106(5) . . ?
H1A N1 H1B 109(6) . . ?
N2 N1 Eu1 110.6(4) . . ?
N2 N1 H1A 107(5) . . ?
N2 N1 H1B 111(5) . . ?
N1 N2 H2 118(7) . . ?
C1 N2 N1 117.6(6) . . ?
C1 N2 H2 120(7) . . ?
Eu1 N3 H3A 112(4) . . ?
Eu1 N3 H3B 114(5) . . ?
H3A N3 H3B 108(6) . . ?
N4 N3 Eu1 111.8(3) . . ?
N4 N3 H3A 105(4) . . ?
N4 N3 H3B 106(5) . . ?
N3 N4 H4 119(5) . . ?
C8 N4 N3 117.7(5) . . ?
C8 N4 H4 123(5) . . ?
O4 N5 O3 117.0(18) . . ?
O4 N5 O5 118.9(17) . . ?
O5 N5 O3 118.8(14) . . ?
O7 N6 O6 119.3(10) . . ?
O7 N6 O8 121.3(11) . . ?
O8 N6 O6 119.3(11) . . ?
O7A N6A O6A 117.2(19) . . ?
O7A N6A O8A 121(2) . . ?
O8A N6A O6A 121(2) . . ?
O9 N7 O10 119.3(9) . . ?
O9 N7 O11 119.7(9) . . ?
O11 N7 O10 119.8(9) . . ?
O1 C1 N2 121.8(7) . . ?
O1 C1 C2 118.5(14) . . ?
O1 C1 C2A 124.5(14) . . ?
N2 C1 C2 119.6(15) . . ?
N2 C1 C2A 113.7(14) . . ?
C3 C2 C1 119.3(13) . . ?
C3 C2 C7 115.1(13) . . ?
C7 C2 C1 125.3(13) . . ?
C3A C2A C1 116.2(13) . . ?
C3A C2A C7A 123.5(13) . . ?
C7A C2A C1 120.0(13) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 C2 122.1(13) . . ?
C4 C3 H3 118.9 . . ?
C2A C3A H3AA 121.3 . . ?
C2A C3A C4A 117.4(13) . . ?
C4A C3A H3AA 121.3 . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 C3 120.4(15) . . ?
C5 C4 H4A 119.8 . . ?
C3A C4A H4AA 120.8 . . ?
C5A C4A C3A 118.4(15) . . ?
C5A C4A H4AA 120.8 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.7(15) . . ?
C6 C5 H5 120.1 . . ?
C4A C5A H5A 118.6 . . ?
C4A C5A C6A 122.9(15) . . ?
C6A C5A H5A 118.6 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.8(15) . . ?
C7 C6 H6 120.1 . . ?
C5A C6A H6A 120.3 . . ?
C7A C6A C5A 119.5(15) . . ?
C7A C6A H6A 120.3 . . ?
C2 C7 H7 118.7 . . ?
C6 C7 C2 122.5(15) . . ?
C6 C7 H7 118.7 . . ?
C2A C7A H7A 121.2 . . ?
C6A C7A C2A 117.5(14) . . ?
C6A C7A H7A 121.2 . . ?
O2 C8 N4 121.1(5) . . ?
O2 C8 C9 120.5(5) . . ?
N4 C8 C9 118.3(5) . . ?
C10 C9 C8 123.2(6) . . ?
C10 C9 C14 119.2(6) . . ?
C14 C9 C8 117.7(6) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.7(7) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.4(8) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.6(7) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.7(8) . . ?
C14 C13 H13 120.2 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.4(7) . . ?
C13 C14 H14 119.8 . . ?
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
Eu1 O1 2.380(4) . ?
Eu1 O1 2.380(4) 2_656 ?
Eu1 O2 2.409(4) . ?
Eu1 O2 2.409(4) 2_656 ?
Eu1 O3 2.522(8) . ?
Eu1 N1 2.601(7) . ?
Eu1 N1 2.601(7) 2_656 ?
Eu1 N3 2.630(6) 2_656 ?
Eu1 N3 2.630(6) . ?
O1 C1 1.244(7) . ?
O2 C8 1.246(6) . ?
O3 N5 1.268(11) . ?
O4 N5 1.261(14) . ?
O5 N5 1.265(15) . ?
O6 N6 1.247(10) . ?
O6A N6A 1.257(16) . ?
O7 N6 1.224(10) . ?
O7A N6A 1.213(15) . ?
O8 N6 1.238(10) . ?
O8A N6A 1.243(15) . ?
O9 N7 1.433(16) . ?
O10 N7 1.456(16) . ?
O11 N7 1.448(16) . ?
N1 H1A 0.888(10) . ?
N1 H1B 0.888(10) . ?
N1 N2 1.412(10) . ?
N2 H2 0.859(11) . ?
N2 C1 1.326(8) . ?
N3 H3A 0.890(10) . ?
N3 H3B 0.890(10) . ?
N3 N4 1.413(7) . ?
N4 H4 0.860(10) . ?
N4 C8 1.320(7) . ?
C1 C2 1.508(13) . ?
C1 C2A 1.456(13) . ?
C2 C3 1.397(18) . ?
C2 C7 1.402(15) . ?
C2A C3A 1.383(19) . ?
C2A C7A 1.395(16) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(15) . ?
C3A H3AA 0.9300 . ?
C3A C4A 1.392(16) . ?
C4 H4A 0.9300 . ?
C4 C5 1.353(17) . ?
C4A H4AA 0.9300 . ?
C4A C5A 1.364(18) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(19) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.384(19) . ?
C6 H6 0.9300 . ?
C6 C7 1.377(16) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.352(17) . ?
C7 H7 0.9300 . ?
C7A H7A 0.9300 . ?
C8 C9 1.484(7) . ?
C9 C10 1.376(9) . ?
C9 C14 1.386(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.356(12) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(12) . ?
C13 H13 0.9300 . ?
C13 C14 1.380(9) . ?
C14 H14 0.9300 . ?
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
N1 H1A O5 0.888(10) 2.07(3) 2.883(11) 152(6) 6_565 yes
N1 H1B O7A 0.888(10) 2.06(4) 2.89(3) 155(7) 5_666 yes
N2 H2 O8A 0.859(11) 2.39(8) 3.02(3) 130(9) 2_655 yes
N3 H3A O8 0.890(10) 2.01(2) 2.893(19) 174(5) 6_566 yes
N3 H3B O5 0.890(10) 2.13(4) 2.945(10) 152(7) 6_565 yes
N4 H4 O6 0.860(10) 2.19(4) 2.931(13) 145(6) . yes
N4 H4 O6A 0.860(10) 2.07(3) 2.89(2) 159(7) . 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
_geom_torsion_publ_flag
Eu1 O1 C1 N2 -12.6(8) . . . . ?
Eu1 O1 C1 C2 163.3(19) . . . . ?
Eu1 O1 C1 C2A 166(2) . . . . ?
Eu1 O2 C8 N4 -12.6(8) . . . . ?
Eu1 O2 C8 C9 168.2(4) . . . . ?
Eu1 O3 N5 O4 167(2) . . . . ?
Eu1 O3 N5 O5 13(7) . . . . ?
Eu1 N1 N2 C1 15.2(8) . . . . ?
Eu1 N3 N4 C8 11.4(7) . . . . ?
O1 C1 C2 C3 -20(4) . . . . ?
O1 C1 C2 C7 154(3) . . . . ?
O1 C1 C2A C3A -47(5) . . . . ?
O1 C1 C2A C7A 139(3) . . . . ?
O2 C8 C9 C10 -161.5(6) . . . . ?
O2 C8 C9 C14 19.2(8) . . . . ?
N1 N2 C1 O1 -3.7(10) . . . . ?
N1 N2 C1 C2 -179.6(19) . . . . ?
N1 N2 C1 C2A 177(2) . . . . ?
N2 C1 C2 C3 156(3) . . . . ?
N2 C1 C2 C7 -30(5) . . . . ?
N2 C1 C2A C3A 132(3) . . . . ?
N2 C1 C2A C7A -42(5) . . . . ?
N3 N4 C8 O2 -0.9(8) . . . . ?
N3 N4 C8 C9 178.3(5) . . . . ?
N4 C8 C9 C10 19.3(8) . . . . ?
N4 C8 C9 C14 -159.9(6) . . . . ?
C1 C2 C3 C4 -178(2) . . . . ?
C1 C2 C7 C6 180(3) . . . . ?
C1 C2A C3A C4A -178(3) . . . . ?
C1 C2A C7A C6A 178(3) . . . . ?
C2 C3 C4 C5 -5(4) . . . . ?
C2A C3A C4A C5A 6(4) . . . . ?
C3 C2 C7 C6 -6(5) . . . . ?
C3 C4 C5 C6 1(3) . . . . ?
C3A C2A C7A C6A 4(6) . . . . ?
C3A C4A C5A C6A -9(3) . . . . ?
C4 C5 C6 C7 1(3) . . . . ?
C4A C5A C6A C7A 9(3) . . . . ?
C5 C6 C7 C2 2(4) . . . . ?
C5A C6A C7A C2A -6(4) . . . . ?
C7 C2 C3 C4 8(5) . . . . ?
C7A C2A C3A C4A -4(6) . . . . ?
C8 C9 C10 C11 178.5(6) . . . . ?
C8 C9 C14 C13 -179.0(6) . . . . ?
C9 C10 C11 C12 1.7(11) . . . . ?
C10 C9 C14 C13 1.7(10) . . . . ?
C10 C11 C12 C13 -0.4(12) . . . . ?
C11 C12 C13 C14 -0.2(12) . . . . ?
C12 C13 C14 C9 -0.4(11) . . . . ?
C14 C9 C10 C11 -2.3(10) . . . . ?
