#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:19:53 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257797 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/96/7059648.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_7059648
loop_
_publ_author_name
'Shi, Zhi-Qiang'
'Ji, Ning-Ning'
'Chen, Wan-Yao'
'Li, Gang'
_publ_section_title
;
 Proton conduction in two hydrogen-bonded supramolecular lanthanide
 complexes
;
_journal_issue                   25
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10562
_journal_page_last               10568
_journal_paper_doi               10.1039/D0NJ02085K
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety
'C22 H24 Eu F2 N4 O14, C11 H6 F N2 O4, 6(H2 O)'
_chemical_formula_sum            'C33 H42 Eu F3 N6 O24'
_chemical_formula_weight         1115.68
_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     direct
_audit_creation_date             2018-07-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-25 deposited with the CCDC.	2020-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                96.834(3)
_cell_angle_beta                 108.861(4)
_cell_angle_gamma                96.387(3)
_cell_formula_units_Z            2
_cell_length_a                   11.4389(5)
_cell_length_b                   12.4406(4)
_cell_length_c                   16.1101(7)
_cell_measurement_reflns_used    6662
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7330
_cell_measurement_theta_min      4.1450
_cell_volume                     2126.54(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -105.00   38.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000    0.0000  -30.0000 143

#__ type_ start__ end____ width___ exp.time_
  2 omega  -45.00   25.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000   90.0000 70

#__ type_ start__ end____ width___ exp.time_
  3 omega   21.00   60.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  150.0000 39

#__ type_ start__ end____ width___ exp.time_
  4 omega   -4.00   41.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -180.0000 45

#__ type_ start__ end____ width___ exp.time_
  5 omega   11.00  101.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
  6 omega   57.00   97.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000    0.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega   42.00   76.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -90.0000 34

#__ type_ start__ end____ width___ exp.time_
  8 omega   14.00   46.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  150.0000 32

#__ type_ start__ end____ width___ exp.time_
  9 omega    4.00   33.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
 10 omega   68.00  108.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 40

#__ type_ start__ end____ width___ exp.time_
 11 omega   47.00   77.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   90.0000 30

#__ type_ start__ end____ width___ exp.time_
 12 omega   44.00  107.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734 -157.0000  -87.0000 63

#__ type_ start__ end____ width___ exp.time_
 13 omega   63.00  105.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  150.0000 42

#__ type_ start__ end____ width___ exp.time_
 14 omega   77.00  109.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
 15 omega   23.00   59.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
 16 omega   57.00  108.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 51

#__ type_ start__ end____ width___ exp.time_
 17 omega   63.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -90.0000 115

#__ type_ start__ end____ width___ exp.time_
 18 omega   38.00  108.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

#__ type_ start__ end____ width___ exp.time_
 19 omega   83.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   42.00   96.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 54

#__ type_ start__ end____ width___ exp.time_
 21 omega   42.00   88.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 46

#__ type_ start__ end____ width___ exp.time_
 22 omega   42.00   68.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   59.00  125.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  120.0000 66

#__ type_ start__ end____ width___ exp.time_
 24 omega   38.00   93.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 25 omega   45.00   86.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 41

#__ type_ start__ end____ width___ exp.time_
 26 omega  121.00  154.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
 27 omega   38.00   99.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 61

#__ type_ start__ end____ width___ exp.time_
 28 omega   56.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
 29 omega   43.00  108.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 65

#__ type_ start__ end____ width___ exp.time_
 30 omega  111.00  137.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 31 omega   38.00   64.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 32 omega   83.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 33 omega  118.00  146.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 28

#__ type_ start__ end____ width___ exp.time_
 34 omega   44.00  114.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1441210000
_diffrn_orient_matrix_UB_12      -0.0228738000
_diffrn_orient_matrix_UB_13      -0.0359701000
_diffrn_orient_matrix_UB_21      -0.0019804000
_diffrn_orient_matrix_UB_22      0.0324811000
_diffrn_orient_matrix_UB_23      0.0947907000
_diffrn_orient_matrix_UB_31      -0.0027560000
_diffrn_orient_matrix_UB_32      0.1199241000
_diffrn_orient_matrix_UB_33      -0.0147517000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15140
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.063
_diffrn_reflns_theta_max         67.063
_diffrn_reflns_theta_min         3.625
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    11.551
_exptl_absorpt_correction_T_max  0.729
_exptl_absorpt_correction_T_min  0.117
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_description       prism
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.3202
_exptl_crystal_size_mid          0.1558
_exptl_crystal_size_min          0.0366
_refine_diff_density_max         0.987
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     639
_refine_ls_number_reflns         7583
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0483
_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)+(0.0730P)²+0.3101P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1287
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6666
_reflns_number_total             7583
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj02085k2.cif
_cod_data_source_block           201807325
_cod_depositor_comments
;Adding full bibliography for 7059647--7059648.cif.

 Adding full bibliography for 7059647--7059648.cif.
;
_cod_database_code               7059648
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C33H33O24N6Eu1F3
_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.
;
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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) groups, All O(H,H) groups
2. Restrained distances
 H10A-O10
 0.9 with sigma of 0.02
 F2A-C21
 1.35 with sigma of 0.02
 C8-F1
 1.35 with sigma of 0.02
 C10-F1A
 1.35 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F1) = Uanis(F1A)
Uanis(F2) = Uanis(F2A)
Uanis(O23) = Uanis(O23A)
Uanis(O20) = Uanis(O20A)
4. Others
 Sof(H8)=Sof(F1A)=1-FVAR(1)
 Sof(H10)=Sof(F1)=FVAR(1)
 Sof(H19)=Sof(F2A)=1-FVAR(2)
 Sof(H21)=Sof(F2)=FVAR(2)
 Sof(O23A)=Sof(H23C)=Sof(H23D)=1-FVAR(3)
 Sof(O23)=Sof(H23A)=Sof(H23B)=FVAR(3)
 Sof(O20A)=Sof(H20C)=Sof(H20D)=1-FVAR(4)
 Sof(O20)=Sof(H20A)=Sof(H20B)=FVAR(4)
5.a Riding coordinates:
 O15(H15A,H15B), O16(H16A,H16B), O19(H19A,H19B), O20A(H20C,H20D), O22(H22A,
 H22B), O23(H23A,H23B), O24(H24A,H24B)
5.b Free rotating group:
 O20(H20A,H20B), O21(H21A,H21B), O23A(H23C,H23D)
5.c Rotating group:
 O13(H13A,H13B), O14(H14A,H14B), O17(H17A,H17B), O18(H18A,H18B)
5.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), N1(H1), N4(H4), C29(H29), C31(H31), C32(H32), C33(H33),
 N6(H6)
5.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O7(H7A)
;
_olex2_date_sample_data_collection 2018-07-11
_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
C1 C 0.2528(5) 0.1048(4) 0.0694(4) 0.0407(11) Uani 1 1 d . . . . .
C2 C 0.2301(5) -0.1414(4) -0.0485(4) 0.0445(12) Uani 1 1 d . . . . .
C3 C 0.3445(5) 0.0280(4) 0.0728(3) 0.0371(11) Uani 1 1 d . . . . .
C4 C 0.3371(5) -0.0714(4) 0.0238(3) 0.0381(11) Uani 1 1 d . . . . .
C5 C 0.5253(5) -0.0287(4) 0.1169(4) 0.0403(11) Uani 1 1 d . . . . .
C6 C 0.6562(5) -0.0318(5) 0.1667(4) 0.0417(12) Uani 1 1 d . . . . .
C7 C 0.7287(6) 0.0529(6) 0.2330(5) 0.0609(16) Uani 1 1 d . . . . .
H7 H 0.6946 0.1138 0.2475 0.073 Uiso 1 1 calc R . . . .
C8 C 0.8511(6) 0.0465(7) 0.2773(5) 0.075(2) Uani 1 1 d D . . . .
H8 H 0.8982 0.1040 0.3222 0.090 Uiso 0.308(8) 1 calc R . P A 2
C9 C 0.9075(6) -0.0391(7) 0.2592(5) 0.071(2) Uani 1 1 d . . . . .
H9 H 0.9910 -0.0414 0.2904 0.085 Uiso 1 1 calc R . . . .
C10 C 0.8356(7) -0.1218(6) 0.1928(6) 0.072(2) Uani 1 1 d D . . . .
H10 H 0.8720 -0.1811 0.1781 0.086 Uiso 0.692(8) 1 calc R . P A 1
C11 C 0.7114(6) -0.1210(5) 0.1467(5) 0.0568(15) Uani 1 1 d . . . . .
H11 H 0.6649 -0.1795 0.1026 0.068 Uiso 1 1 calc R . . . .
C12 C 0.2272(5) 0.6002(4) 0.2927(3) 0.0399(11) Uani 1 1 d . . . . .
C13 C 0.3102(5) 0.8027(5) 0.4663(4) 0.0494(14) Uani 1 1 d . . . . .
C14 C 0.3462(5) 0.6313(4) 0.3699(3) 0.0372(11) Uani 1 1 d . . . . .
C15 C 0.3782(5) 0.7179(4) 0.4384(3) 0.0391(11) Uani 1 1 d . . . . .
C16 C 0.5334(5) 0.6251(4) 0.4528(3) 0.0374(11) Uani 1 1 d . . . . .
C17 C 0.6565(5) 0.5920(5) 0.4897(4) 0.0419(12) Uani 1 1 d . . . . .
C18 C 0.6818(5) 0.4965(5) 0.4488(4) 0.0501(13) Uani 1 1 d . . . . .
H18 H 0.6218 0.4549 0.3980 0.060 Uiso 1 1 calc R . . . .
C19 C 0.7956(6) 0.4646(5) 0.4842(5) 0.0575(15) Uani 1 1 d . . . . .
H19 H 0.8115 0.4010 0.4561 0.069 Uiso 0.110(8) 1 calc R . P B 2
C20 C 0.8869(6) 0.5215(6) 0.5587(5) 0.0600(16) Uani 1 1 d . . . . .
H20 H 0.9630 0.4970 0.5819 0.072 Uiso 1 1 calc R . . . .
C21 C 0.8626(6) 0.6161(6) 0.5984(4) 0.0596(16) Uani 1 1 d D . . . .
H21 H 0.9237 0.6568 0.6491 0.072 Uiso 0.890(8) 1 calc R . P B 1
C22 C 0.7496(5) 0.6523(5) 0.5648(4) 0.0512(14) Uani 1 1 d . . . . .
H22 H 0.7357 0.7172 0.5924 0.061 Uiso 1 1 calc R . . . .
Eu1 Eu 0.18904(2) 0.35521(2) 0.14279(2) 0.03367(11) Uani 1 1 d . . . . .
F1 F 0.9186(7) 0.1264(7) 0.3403(6) 0.116(3) Uani 0.692(8) 1 d D . P A 1
F1A F 0.8904(14) -0.2071(14) 0.1886(13) 0.116(3) Uani 0.308(8) 1 d D . P A 2
F2 F 0.8177(5) 0.3705(4) 0.4473(4) 0.0867(17) Uani 0.890(8) 1 d . . P B 1
F2A F 0.965(2) 0.673(3) 0.659(3) 0.0867(17) Uani 0.110(8) 1 d D . P B 2
N1 N 0.4636(4) 0.0545(4) 0.1312(3) 0.0381(9) Uani 1 1 d . . . . .
H1 H 0.4940 0.1132 0.1701 0.046 Uiso 1 1 calc R . . . .
N2 N 0.4501(4) -0.1065(3) 0.0511(3) 0.0402(9) Uani 1 1 d . . . . .
N3 N 0.4421(4) 0.5729(3) 0.3795(3) 0.0360(9) Uani 1 1 d . . . . .
N4 N 0.4969(4) 0.7124(4) 0.4903(3) 0.0410(10) Uani 1 1 d . . . . .
H4 H 0.5409 0.7566 0.5383 0.049 Uiso 1 1 calc R . . . .
O1 O 0.2889(3) 0.1970(3) 0.1166(3) 0.0473(9) Uani 1 1 d . . . . .
O2 O 0.1411(3) 0.0714(3) 0.0161(3) 0.0533(10) Uani 1 1 d . . . . .
O3 O 0.1236(4) -0.1071(3) -0.0715(3) 0.0531(10) Uani 1 1 d . . . . .
H3 H 0.1297 -0.0479 -0.0408 0.080 Uiso 1 1 calc GR . . . .
O4 O 0.2428(4) -0.2296(3) -0.0848(3) 0.0615(12) Uani 1 1 d . . . . .
O5 O 0.2174(4) 0.5168(3) 0.2378(2) 0.0496(9) Uani 1 1 d . . . . .
O6 O 0.1433(4) 0.6590(3) 0.2862(3) 0.0499(9) Uani 1 1 d . . . . .
O7 O 0.2019(4) 0.8123(4) 0.4118(3) 0.0598(11) Uani 1 1 d . . . . .
H7A H 0.1833 0.7661 0.3669 0.090 Uiso 1 1 calc GR . . . .
O8 O 0.3572(4) 0.8588(4) 0.5409(3) 0.0718(15) Uani 1 1 d . . . . .
O13 O 0.0628(4) 0.2651(4) -0.0031(3) 0.0612(12) Uani 1 1 d . . . . .
H13A H -0.0176 0.2666 -0.0126 0.092 Uiso 1 1 d GR . . . .
H13B H 0.0664 0.1940 -0.0093 0.092 Uiso 1 1 d GR . . . .
O14 O -0.0206(4) 0.3770(4) 0.1388(4) 0.0666(13) Uani 1 1 d . . . . .
H14A H -0.0754 0.3334 0.0940 0.100 Uiso 1 1 d GR . . . .
H14B H -0.0348 0.4417 0.1280 0.100 Uiso 1 1 d GR . . . .
O15 O 0.1326(4) 0.4975(3) 0.0494(3) 0.0535(10) Uani 1 1 d . . . . .
H15A H 0.1055 0.5052 -0.0039 0.080 Uiso 1 1 d R . . . .
H15B H 0.1673 0.5633 0.0801 0.080 Uiso 1 1 d R . . . .
O16 O 0.1021(4) 0.2115(3) 0.2041(3) 0.0492(9) Uani 1 1 d . . . . .
H16A H 0.0349 0.1859 0.1477 0.074 Uiso 1 1 d R . . . .
H16B H 0.1498 0.1614 0.2125 0.074 Uiso 1 1 d R . . . .
O17 O 0.3664(4) 0.3576(4) 0.2731(3) 0.0597(11) Uani 1 1 d . . . . .
H17A H 0.4158 0.4206 0.2868 0.090 Uiso 1 1 d GR . . . .
H17B H 0.4130 0.3109 0.2623 0.090 Uiso 1 1 d GR . . . .
O18 O 0.3541(5) 0.4109(4) 0.0889(4) 0.0765(15) Uani 1 1 d . . . . .
H18A H 0.3250 0.4257 0.0323 0.115 Uiso 1 1 d GR . . . .
H18B H 0.3976 0.3553 0.0820 0.115 Uiso 1 1 d GR . . . .
C23 C 0.6877(5) -0.0367(5) 0.6914(4) 0.0501(14) Uani 1 1 d . . . . .
C24 C 0.7721(7) 0.1947(5) 0.8397(4) 0.0585(17) Uani 1 1 d . . . . .
C25 C 0.6209(5) 0.0566(4) 0.7049(4) 0.0412(11) Uani 1 1 d . . . . .
C26 C 0.6502(5) 0.1512(4) 0.7646(4) 0.0421(12) Uani 1 1 d . . . . .
C27 C 0.4597(5) 0.1458(4) 0.6798(4) 0.0412(11) Uani 1 1 d . . . . .
C28 C 0.3340(6) 0.1707(5) 0.6381(4) 0.0497(13) Uani 1 1 d . . . . .
C29 C 0.2968(8) 0.2612(6) 0.6731(5) 0.0676(19) Uani 1 1 d . . . . .
H29 H 0.3523 0.3084 0.7228 0.081 Uiso 1 1 calc R . . . .
C30 C 0.1784(10) 0.2818(9) 0.6349(7) 0.090(3) Uani 1 1 d . . . . .
C31 C 0.0931(9) 0.2150(10) 0.5622(8) 0.104(4) Uani 1 1 d . . . . .
H31 H 0.0127 0.2308 0.5375 0.124 Uiso 1 1 calc R . . . .
C32 C 0.1285(8) 0.1245(8) 0.5265(7) 0.094(3) Uani 1 1 d . . . . .
H32 H 0.0720 0.0778 0.4769 0.113 Uiso 1 1 calc R . . . .
C33 C 0.2490(7) 0.1023(7) 0.5643(6) 0.073(2) Uani 1 1 d . . . . .
H33 H 0.2728 0.0406 0.5397 0.087 Uiso 1 1 calc R . . . .
F3 F 0.1430(8) 0.3716(7) 0.6689(5) 0.155(3) Uani 1 1 d . . . . .
N5 N 0.5504(5) 0.2068(4) 0.7499(3) 0.0455(10) Uani 1 1 d . . . . .
N6 N 0.5014(4) 0.0547(4) 0.6521(3) 0.0409(10) Uani 1 1 d . . . . .
H6 H 0.4587 0.0041 0.6081 0.049 Uiso 1 1 calc R . . . .
O9 O 0.6349(5) -0.1128(4) 0.6317(4) 0.0854(18) Uani 1 1 d . . . . .
O10 O 0.7977(4) -0.0334(4) 0.7456(4) 0.0690(13) Uani 1 1 d D . . . .
H10A H 0.815(6) 0.029(3) 0.785(3) 0.046(17) Uiso 1 1 d D . . . .
O11 O 0.8604(5) 0.1388(4) 0.8493(3) 0.0765(15) Uani 1 1 d . . . . .
O12 O 0.7818(6) 0.2819(4) 0.8878(3) 0.0837(17) Uani 1 1 d . . . . .
O19 O 0.4726(7) 0.6223(5) 0.1235(6) 0.135(3) Uani 1 1 d . . . . .
H19A H 0.4563 0.6700 0.1588 0.202 Uiso 1 1 d R . . . .
H19B H 0.4081 0.6267 0.0683 0.202 Uiso 1 1 d R . . . .
O20 O 0.5237(8) 0.3161(8) 0.0339(7) 0.124(4) Uani 0.826(10) 1 d . . P C 1
H20A H 0.4842 0.3085 -0.0220 0.186 Uiso 0.826(10) 1 d G . P C 1
H20B H 0.6027 0.3195 0.0509 0.186 Uiso 0.826(10) 1 d G . P C 1
O20A O 0.594(4) 0.341(3) 0.144(4) 0.124(4) Uani 0.174(10) 1 d . . P C 2
H20C H 0.6291 0.4041 0.1413 0.186 Uiso 0.174(10) 1 d R . P C 2
H20D H 0.5537 0.3127 0.0907 0.186 Uiso 0.174(10) 1 d R . P C 2
O21 O 0.4458(5) 0.7665(4) 0.7112(4) 0.0706(13) Uani 1 1 d . . . . .
H21A H 0.4035 0.7212 0.7302 0.106 Uiso 1 1 d G . . . .
H21B H 0.4007 0.7653 0.6574 0.106 Uiso 1 1 d G . . . .
O22 O 0.9235(5) 0.5829(4) 0.1433(3) 0.0701(13) Uani 1 1 d . . . . .
H22A H 0.8855 0.6240 0.0993 0.105 Uiso 1 1 d R . . . .
H22B H 0.9613 0.6141 0.1968 0.105 Uiso 1 1 d R . . . .
O23 O 0.6915(15) 0.4971(15) 0.1602(13) 0.114(4) Uani 0.452(11) 1 d . . P D 1
H23A H 0.6727 0.5231 0.2046 0.170 Uiso 0.452(11) 1 d R . P D 1
H23B H 0.7600 0.5368 0.1659 0.170 Uiso 0.452(11) 1 d R . P D 1
O23A O 0.6725(13) 0.5541(13) 0.0987(11) 0.114(4) Uani 0.548(11) 1 d . . P D 2
H23C H 0.6178 0.5830 0.1151 0.170 Uiso 0.548(11) 1 d G . P D 2
H23D H 0.6472 0.4765 0.0761 0.170 Uiso 0.548(11) 1 d G . P D 2
O24 O 0.2510(15) 0.6504(12) 0.7477(10) 0.285(10) Uani 1 1 d . . . . .
H24A H 0.2239 0.6736 0.7886 0.427 Uiso 1 1 d R . . . .
H24B H 0.1969 0.6499 0.6928 0.427 Uiso 1 1 d R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -8.9294 11.1857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 8 -4 0.1135 0.1857 7.6600 -4.4571 -0.0417 -0.1741 0.9839
-3 7 5 0.1033 -3.2828 6.6526 4.5554 0.1571 0.6544 0.7397
-4 4 8 0.1090 -4.1711 3.8522 8.1922 0.2184 0.9099 0.3526
3 -6 -5 0.0498 3.4899 -6.2704 -5.2620 -0.1703 -0.7094 -0.6840
4 -1 -10 0.0574 4.2327 -1.0353 -9.8148 -0.2333 -0.9724 0.0090
6 1 2 0.0252 5.9618 1.3550 2.1054 -0.9659 0.2318 0.1150
1 -8 3 0.1285 1.1441 -7.9118 2.9620 -0.0905 0.0215 -0.9957
-6 -1 -2 0.0010 -6.0455 -0.7135 -2.3417 0.9718 -0.2332 -0.0344
-7 4 3 0.0734 -7.0106 4.0048 2.9960 0.8110 0.4280 0.4554
-7 -2 5 0.1120 -7.0008 -1.9939 5.0011 0.8747 0.4232 -0.2936
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 C1 C3 119.0(5) . . ?
O1 C1 O2 124.1(5) . . ?
O2 C1 C3 116.9(4) . . ?
O3 C2 C4 118.2(4) . . ?
O4 C2 C4 120.8(5) . . ?
O4 C2 O3 121.1(5) . . ?
C4 C3 C1 132.6(5) . . ?
N1 C3 C1 120.7(4) . . ?
N1 C3 C4 106.7(4) . . ?
C3 C4 C2 130.8(5) . . ?
N2 C4 C2 119.6(5) . . ?
N2 C4 C3 109.6(5) . . ?
N1 C5 C6 124.3(5) . . ?
N2 C5 C6 125.1(5) . . ?
N2 C5 N1 110.6(5) . . ?
C7 C6 C5 121.8(5) . . ?
C7 C6 C11 118.3(5) . . ?
C11 C6 C5 119.9(5) . . ?
C8 C7 C6 119.5(6) . . ?
C9 C8 C7 123.5(7) . . ?
F1 C8 C7 119.1(8) . . ?
F1 C8 C9 117.4(7) . . ?
C8 C9 C10 116.6(6) . . ?
C9 C10 C11 122.7(6) . . ?
F1A C10 C9 112.5(10) . . ?
F1A C10 C11 123.8(10) . . ?
C10 C11 C6 119.4(6) . . ?
O5 C12 C14 117.6(5) . . ?
O5 C12 O6 123.9(5) . . ?
O6 C12 C14 118.5(4) . . ?
O7 C13 C15 118.3(5) . . ?
O8 C13 C15 119.1(5) . . ?
O8 C13 O7 122.6(5) . . ?
C15 C14 C12 128.2(5) . . ?
N3 C14 C12 121.5(4) . . ?
N3 C14 C15 110.3(5) . . ?
C14 C15 C13 134.3(5) . . ?
N4 C15 C13 119.9(4) . . ?
N4 C15 C14 105.7(4) . . ?
N3 C16 C17 125.1(5) . . ?
N3 C16 N4 110.9(4) . . ?
N4 C16 C17 124.0(5) . . ?
C18 C17 C16 119.3(5) . . ?
C22 C17 C16 122.4(5) . . ?
C22 C17 C18 118.3(5) . . ?
C19 C18 C17 119.3(6) . . ?
C20 C19 C18 123.2(6) . . ?
F2 C19 C18 119.2(6) . . ?
F2 C19 C20 117.5(6) . . ?
C19 C20 C21 117.6(6) . . ?
C20 C21 C22 121.4(6) . . ?
F2A C21 C20 111.2(16) . . ?
F2A C21 C22 126.3(17) . . ?
C21 C22 C17 120.2(6) . . ?
O1 Eu1 O15 128.51(14) . . ?
O5 Eu1 O1 142.79(13) . . ?
O5 Eu1 O13 140.48(15) . . ?
O5 Eu1 O14 75.95(15) . . ?
O5 Eu1 O15 73.19(14) . . ?
O5 Eu1 O16 107.19(14) . . ?
O5 Eu1 O17 71.54(14) . . ?
O5 Eu1 O18 95.57(17) . . ?
O13 Eu1 O1 75.70(14) . . ?
O13 Eu1 O14 77.31(17) . . ?
O13 Eu1 O15 72.29(15) . . ?
O13 Eu1 O16 89.53(15) . . ?
O13 Eu1 O17 147.69(15) . . ?
O13 Eu1 O18 90.09(19) . . ?
O14 Eu1 O1 133.94(14) . . ?
O14 Eu1 O15 75.47(16) . . ?
O16 Eu1 O1 74.05(13) . . ?
O16 Eu1 O14 69.10(15) . . ?
O16 Eu1 O15 142.99(14) . . ?
O17 Eu1 O1 71.99(13) . . ?
O17 Eu1 O14 126.36(17) . . ?
O17 Eu1 O15 130.37(15) . . ?
O17 Eu1 O16 81.24(15) . . ?
O18 Eu1 O1 71.07(15) . . ?
O18 Eu1 O14 145.19(18) . . ?
O18 Eu1 O15 69.78(16) . . ?
O18 Eu1 O16 144.07(15) . . ?
O18 Eu1 O17 80.10(19) . . ?
C5 N1 C3 107.3(4) . . ?
C5 N2 C4 105.8(4) . . ?
C16 N3 C14 105.4(4) . . ?
C16 N4 C15 107.8(4) . . ?
C1 O1 Eu1 135.0(3) . . ?
C12 O5 Eu1 175.0(4) . . ?
O9 C23 C25 119.4(5) . . ?
O9 C23 O10 123.0(6) . . ?
O10 C23 C25 117.6(5) . . ?
O11 C24 C26 117.7(6) . . ?
O12 C24 C26 119.2(7) . . ?
O12 C24 O11 123.0(7) . . ?
C26 C25 C23 134.6(5) . . ?
N6 C25 C23 120.1(5) . . ?
N6 C25 C26 105.3(5) . . ?
C25 C26 C24 128.0(6) . . ?
C25 C26 N5 110.8(5) . . ?
N5 C26 C24 121.2(5) . . ?
N5 C27 C28 126.4(5) . . ?
N5 C27 N6 109.6(5) . . ?
N6 C27 C28 124.0(5) . . ?
C29 C28 C27 120.4(6) . . ?
C29 C28 C33 118.5(6) . . ?
C33 C28 C27 121.1(5) . . ?
C30 C29 C28 119.8(9) . . ?
C29 C30 C31 122.5(8) . . ?
F3 C30 C29 119.5(11) . . ?
F3 C30 C31 118.0(9) . . ?
C32 C31 C30 118.5(8) . . ?
C31 C32 C33 119.9(10) . . ?
C28 C33 C32 120.9(8) . . ?
C27 N5 C26 105.3(4) . . ?
C25 N6 C27 109.0(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
C1 C3 1.487(7) . ?
C1 O1 1.244(6) . ?
C1 O2 1.277(6) . ?
C2 C4 1.488(7) . ?
C2 O3 1.291(7) . ?
C2 O4 1.227(6) . ?
C3 C4 1.364(7) . ?
C3 N1 1.360(7) . ?
C4 N2 1.363(7) . ?
C5 C6 1.459(7) . ?
C5 N1 1.354(7) . ?
C5 N2 1.335(7) . ?
C6 C7 1.379(9) . ?
C6 C11 1.393(8) . ?
C7 C8 1.366(9) . ?
C8 C9 1.355(11) . ?
C8 F1 1.303(9) . ?
C9 C10 1.363(11) . ?
C10 C11 1.375(9) . ?
C10 F1A 1.297(14) . ?
C12 C14 1.491(7) . ?
C12 O5 1.250(6) . ?
C12 O6 1.255(6) . ?
C13 C15 1.488(7) . ?
C13 O7 1.293(7) . ?
C13 O8 1.233(7) . ?
C14 C15 1.372(7) . ?
C14 N3 1.360(7) . ?
C15 N4 1.359(7) . ?
C16 C17 1.467(7) . ?
C16 N3 1.333(6) . ?
C16 N4 1.351(7) . ?
C17 C18 1.393(8) . ?
C17 C22 1.391(8) . ?
C18 C19 1.366(8) . ?
C19 C20 1.362(10) . ?
C19 F2 1.337(8) . ?
C20 C21 1.371(10) . ?
C21 C22 1.378(8) . ?
C21 F2A 1.318(19) . ?
Eu1 O1 2.444(4) . ?
Eu1 O5 2.300(3) . ?
Eu1 O13 2.384(4) . ?
Eu1 O14 2.424(4) . ?
Eu1 O15 2.465(4) . ?
Eu1 O16 2.412(4) . ?
Eu1 O17 2.396(4) . ?
Eu1 O18 2.390(5) . ?
C23 C25 1.492(8) . ?
C23 O9 1.211(7) . ?
C23 O10 1.271(7) . ?
C24 C26 1.512(8) . ?
C24 O11 1.269(10) . ?
C24 O12 1.227(8) . ?
C25 C26 1.363(8) . ?
C25 N6 1.352(7) . ?
C26 N5 1.370(7) . ?
C27 C28 1.464(8) . ?
C27 N5 1.338(7) . ?
C27 N6 1.359(7) . ?
C28 C29 1.370(9) . ?
C28 C33 1.382(10) . ?
C29 C30 1.363(12) . ?
C30 C31 1.365(15) . ?
C30 F3 1.346(10) . ?
C31 C32 1.364(14) . ?
C32 C33 1.389(10) . ?
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
N4 H4 O9 0.86 2.01 2.854(6) 166.3 1_565
O3 H3 O2 0.82 1.62 2.436(5) 177.5 .
O7 H7A O6 0.82 1.66 2.470(5) 171.3 .
O13 H13B O2 0.89 1.85 2.680(6) 154.5 .
O14 H14A O4 0.86 2.14 2.781(6) 130.7 2
O14 H14B O22 0.86 1.88 2.706(6) 159.3 1_455
O15 H15B O12 0.88 1.91 2.759(6) 162.5 2_666
O16 H16A O3 0.97 1.91 2.818(5) 155.5 2
O16 H16B O10 0.87 1.89 2.696(6) 154.8 2_656
O17 H17A N3 0.87 2.19 2.881(6) 135.1 .
O17 H17B O21 0.87 1.93 2.746(7) 156.3 2_666
O18 H18B O20 0.91 1.92 2.703(8) 142.1 .
O18 H18B O20A 0.91 2.19 2.87(4) 131.1 .
N6 H6 O8 0.86 2.01 2.834(6) 159.9 1_545
O10 H10A O11 0.90(2) 1.54(2) 2.435(7) 172(6) .
O19 H19A N5 0.85 2.02 2.861(7) 170.1 2_666
O19 H19B O20 0.97 2.19 2.748(15) 115.1 2_665
O20 H20A N2 0.86 2.73 2.890(9) 91.9 2_655
O20 H20A O19 0.86 2.10 2.748(15) 131.7 2_665
O20 H20B O4 0.85 2.15 2.897(10) 146.2 2_655
O20 H20B O23 0.85 2.54 2.88(2) 105.7 .
O21 H21A O24 0.85 1.98 2.779(13) 155.9 .
O22 H22B O6 0.85 2.08 2.779(6) 139.0 1_655
O23 H23B O22 0.85 2.05 2.856(18) 157.7 .
O23A H23C O19 0.85 1.82 2.655(15) 165.0 .
