#------------------------------------------------------------------------------
#$Date: 2021-07-21 03:01:41 +0300 (Wed, 21 Jul 2021) $
#$Revision: 267658 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/00/05/8000519.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_8000519
loop_
_publ_author_name
'Okayasu, Yoshinori'
'Yuasa, Junpei'
_publ_section_title
;
 Structure Determination of Europium Complexes in Solution Using
 Crystal-Field Splitting of the Narrow f-f Emission Lines.
;
_journal_name_full               'The journal of physical chemistry letters'
_journal_page_first              6867
_journal_page_last               6874
_journal_paper_doi               10.1021/acs.jpclett.1c01885
_journal_year                    2021
_chemical_absolute_configuration rm
_chemical_formula_sum            'C56 H43 Eu F9 N3 O11'
_chemical_formula_weight         1256.89
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                100.881(10)
_cell_angle_beta                 109.334(9)
_cell_angle_gamma                97.095(12)
_cell_formula_units_Z            1
_cell_length_a                   10.396(7)
_cell_length_b                   11.164(7)
_cell_length_c                   12.730(8)
_cell_measurement_reflns_used    525
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.1756
_cell_measurement_theta_min      1.7740
_cell_volume                     1341.2(15)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7467
_diffrn_reflns_point_group_measured_fraction_full 0.560
_diffrn_reflns_point_group_measured_fraction_max 0.486
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.312
_diffrn_reflns_theta_min         1.749
_exptl_absorpt_coefficient_mu    1.264
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_description       Plate
_exptl_crystal_F_000             632
_refine_diff_density_max         0.857
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.004(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     722
_refine_ls_number_reflns         6469
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      0.912
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0232
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0504
_refine_ls_wR_factor_ref         0.0504
_reflns_Friedel_coverage         0.124
_reflns_Friedel_fraction_full    0.145
_reflns_Friedel_fraction_max     0.107
_reflns_number_gt                6449
_reflns_number_total             6469
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jz1c01885_si_009.cif
_cod_data_source_block           PhEuOMe_0m_b
_cod_database_code               8000519
_shelx_shelxl_version_number     2016/6
_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.
;
loop_
_space_group_symop_operation_xyz
'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
F23A F 0.9028(8) 0.5568(7) 0.6142(8) 0.0652(13) Uani 0.574(5) 1 d D U P A 1
F23B F 0.8480(12) 0.7161(9) 0.7015(9) 0.0652(13) Uani 0.574(5) 1 d D U P A 1
F23C F 0.8958(7) 0.5578(6) 0.7765(7) 0.0652(13) Uani 0.574(5) 1 d D U P A 1
F23D F 0.9295(9) 0.5460(9) 0.6830(12) 0.0652(13) Uani 0.426(5) 1 d D . P A 2
F23E F 0.8496(17) 0.7082(13) 0.6628(13) 0.0652(13) Uani 0.426(5) 1 d D . P A 2
F23F F 0.8484(9) 0.6163(8) 0.8028(9) 0.0652(13) Uani 0.426(5) 1 d D . P A 2
Eu1 Eu 0.47001(2) 0.23433(2) 0.53095(2) 0.01145(5) Uani 1 1 d . . . . .
O11 O 0.0686(4) 0.8628(3) 0.3991(4) 0.0265(10) Uani 1 1 d . . . . .
F12C F 0.8718(3) 0.0116(3) 0.6125(3) 0.0366(8) Uani 1 1 d . . . . .
F1A F 0.4308(3) -0.1581(2) 0.2215(3) 0.0392(8) Uani 1 1 d . . . . .
O2 O 0.3808(3) 0.4431(3) 0.8532(2) 0.0224(7) Uani 1 1 d . . . . .
C45 C -0.0200(6) 0.2884(5) 0.5927(5) 0.0214(13) Uani 1 1 d . . . . .
H45 H -0.104979 0.299376 0.602349 0.026 Uiso 1 1 calc R U . . .
N3 N 0.4792(4) 0.3393(3) 0.7384(3) 0.0149(8) Uani 1 1 d . . . . .
O5 O 0.8313(4) 0.6361(3) 0.1514(3) 0.0333(9) Uani 1 1 d . . . . .
N2 N 0.2289(4) 0.2532(3) 0.5656(3) 0.0137(7) Uani 1 1 d . . . . .
O7 O 0.3947(3) 0.0683(2) 0.6050(2) 0.0157(6) Uani 1 1 d . . . . .
C40 C 0.1995(5) 0.0826(4) 0.2354(3) 0.0193(10) Uani 1 1 d . . . . .
H40 H 0.261082 0.022305 0.226851 0.023 Uiso 1 1 calc R U . . .
F1C F 0.6214(3) -0.1465(2) 0.3621(3) 0.0320(7) Uani 1 1 d . . . . .
O8 O 0.1559(4) -0.2299(3) 0.8981(3) 0.0267(8) Uani 1 1 d . . . . .
C32 C 0.1478(5) 0.7738(4) 0.4219(4) 0.0179(10) Uani 1 1 d . . . . .
C48 C 0.3690(6) 0.3682(5) 0.7526(4) 0.0155(11) Uani 1 1 d . . . . .
C5 C 0.6714(5) 0.3594(4) 0.2789(3) 0.0167(9) Uani 1 1 d . . . . .
O3 O 0.4947(3) 0.0541(3) 0.4002(2) 0.0172(7) Uani 1 1 d . . . . .
C50 C 0.5969(5) 0.3920(4) 0.8512(4) 0.0196(10) Uani 1 1 d . . . . .
H50 H 0.676372 0.440958 0.839847 0.023 Uiso 1 1 calc R U . . .
C7 C 0.6201(5) 0.4691(4) 0.2731(4) 0.0188(10) Uani 1 1 d . . . . .
H7 H 0.545671 0.481759 0.298771 0.023 Uiso 1 1 calc R U . . .
O6 O 0.6721(3) 0.1651(2) 0.6293(2) 0.0165(6) Uani 1 1 d . . . . .
C51 C 0.6435(5) 0.2881(4) 0.9058(4) 0.0190(10) Uani 1 1 d . . . . .
C30 C 0.2799(5) 0.7999(4) 0.4143(4) 0.0196(10) Uani 1 1 d . . . . .
H30 H 0.305706 0.871012 0.389340 0.024 Uiso 1 1 calc R U . . .
C21 C 0.2262(5) -0.1878(4) 0.8339(4) 0.0202(10) Uani 1 1 d . . . . .
C29 C 0.2007(5) 0.5887(4) 0.4803(4) 0.0184(10) Uani 1 1 d . . . . .
H29 H 0.172128 0.514234 0.499511 0.022 Uiso 1 1 calc R U . . .
C4 C 0.6060(5) 0.2636(4) 0.3223(3) 0.0165(9) Uani 1 1 d . . . . .
C9 C 0.6754(6) 0.5585(4) 0.2309(4) 0.0212(10) Uani 1 1 d . . . . .
H9 H 0.638016 0.631586 0.225715 0.025 Uiso 1 1 calc R U . . .
C12 C 0.8391(5) 0.0508(4) 0.7058(4) 0.0242(11) Uani 1 1 d . . . . .
C42 C 0.1182(5) 0.1398(3) 0.3724(4) 0.0144(9) Uani 1 1 d . . . . .
C56 C 0.7241(8) 0.0967(7) 1.0051(6) 0.0287(17) Uani 1 1 d . . . . .
H56 H 0.752586 0.031308 1.039647 0.034 Uiso 1 1 calc R U . . .
F12A F 0.9320(3) 0.1567(2) 0.7674(2) 0.0273(6) Uani 1 1 d . . . . .
C3 C 0.6173(5) 0.1369(4) 0.2923(4) 0.0173(11) Uani 1 1 d . . . . .
H3 H 0.668167 0.114869 0.244401 0.021 Uiso 1 1 calc R U . . .
C10 C 0.7877(5) 0.5415(4) 0.1954(4) 0.0227(11) Uani 1 1 d . . . . .
N1 N 0.2345(4) 0.1415(3) 0.3589(3) 0.0142(8) Uani 1 1 d . . . . .
O4 O 0.5392(3) 0.2992(3) 0.3857(2) 0.0189(7) Uani 1 1 d . . . . .
C37 C 0.2146(5) 0.1413(5) 0.0577(4) 0.0283(12) Uani 1 1 d . . . . .
H37 H 0.213457 0.056358 0.027867 0.034 Uiso 1 1 calc R U . . .
F1B F 0.6305(3) -0.1038(2) 0.2066(3) 0.0387(8) Uani 1 1 d . . . . .
C2 C 0.5584(5) 0.0464(4) 0.3294(4) 0.0150(10) Uani 1 1 d . . . . .
C41 C 0.0494(5) 0.0126(4) 0.1993(4) 0.0250(11) Uani 1 1 d . . . . .
H41A H -0.006624 0.015114 0.120199 0.030 Uiso 1 1 calc R U . . .
H41B H 0.046386 -0.075317 0.203409 0.030 Uiso 1 1 calc R U . . .
O9 O 0.6657(3) 0.4084(3) 0.6209(3) 0.0203(7) Uani 1 1 d . . . . .
C15 C 0.4519(5) -0.0052(4) 0.6619(3) 0.0161(9) Uani 1 1 d . . . . .
C47 C 0.2282(5) 0.3208(4) 0.6645(3) 0.0150(9) Uani 1 1 d . . . . .
C19 C 0.3383(5) -0.2343(4) 0.8163(4) 0.0235(10) Uani 1 1 d . . . . .
H19 H 0.366620 -0.303189 0.844950 0.028 Uiso 1 1 calc R U . . .
C8 C 0.8439(5) 0.4361(4) 0.2037(4) 0.0216(10) Uani 1 1 d . . . . .
H8 H 0.922204 0.426013 0.182600 0.026 Uiso 1 1 calc R U . . .
C54 C 0.5887(5) 0.1137(5) 0.9823(4) 0.0300(12) Uani 1 1 d . . . . .
H54 H 0.524276 0.060345 0.999797 0.036 Uiso 1 1 calc R U . . .
C27 C 0.3345(5) 0.6157(4) 0.4786(3) 0.0143(9) Uani 1 1 d . . . . .
C53 C 0.7773(6) 0.2681(5) 0.9286(4) 0.0219(11) Uani 1 1 d . . . . .
H53 H 0.841676 0.319874 0.909843 0.026 Uiso 1 1 calc R U . . .
C43 C 0.1052(4) 0.2047(4) 0.4805(4) 0.0143(9) Uani 1 1 d . . . . .
C39 C 0.2140(6) 0.1804(5) 0.1694(4) 0.0193(11) Uani 1 1 d . . . . .
C34 C 0.2233(8) 0.3512(8) 0.0345(6) 0.039(2) Uani 1 1 d . . . . .
H34 H 0.227208 0.409207 -0.010745 0.046 Uiso 1 1 calc R U . . .
C6 C 0.7837(5) 0.3457(4) 0.2433(4) 0.0205(10) Uani 1 1 d . . . . .
H6 H 0.819685 0.271725 0.246516 0.025 Uiso 1 1 calc R U . . .
C36 C 0.2237(5) 0.3905(5) 0.1448(4) 0.0301(12) Uani 1 1 d . . . . .
H36 H 0.227354 0.475911 0.175070 0.036 Uiso 1 1 calc R U . . .
C52 C 0.5497(5) 0.2104(4) 0.9332(4) 0.0259(11) Uani 1 1 d . . . . .
H52 H 0.457643 0.224194 0.917832 0.031 Uiso 1 1 calc R U . . .
C31 C 0.1083(5) 0.6683(4) 0.4545(4) 0.0202(10) Uani 1 1 d . . . . .
H31 H 0.018941 0.650400 0.459358 0.024 Uiso 1 1 calc R U . . .
C14 C 0.5940(4) -0.0144(4) 0.6865(4) 0.0165(9) Uani 1 1 d . . . . .
H14 H 0.624968 -0.081953 0.716189 0.020 Uiso 1 1 calc R U . . .
F12B F 0.8659(3) -0.0323(3) 0.7703(3) 0.0411(8) Uani 1 1 d . . . . .
C38 C 0.2187(5) 0.3052(4) 0.2120(4) 0.0238(10) Uani 1 1 d . . . . .
H38 H 0.218604 0.333165 0.287203 0.029 Uiso 1 1 calc R U . . .
O10 O 0.3843(3) 0.4210(2) 0.5052(2) 0.0150(6) Uani 1 1 d . . . . .
C25 C 0.5781(5) 0.5871(4) 0.5704(4) 0.0224(10) Uani 1 1 d . . . . .
H25 H 0.607748 0.672025 0.573102 0.027 Uiso 1 1 calc R U . . .
C1 C 0.5611(5) -0.0905(4) 0.2795(4) 0.0249(11) Uani 1 1 d . . . . .
C28 C 0.3714(5) 0.7222(4) 0.4432(4) 0.0187(10) Uani 1 1 d . . . . .
H28 H 0.461048 0.740790 0.439212 0.022 Uiso 1 1 calc R U . . .
C35 C 0.2170(5) 0.2254(6) -0.0088(4) 0.0357(13) Uani 1 1 d . . . . .
H35 H 0.214422 0.197225 -0.084842 0.043 Uiso 1 1 calc R U . . .
O1 O -0.0011(3) 0.0807(3) 0.2834(3) 0.0220(7) Uani 1 1 d . . . . .
C24 C 0.6777(5) 0.5213(4) 0.6189(4) 0.0222(10) Uani 1 1 d . . . . .
C33 C -0.0582(5) 0.8499(4) 0.4191(4) 0.0238(11) Uani 1 1 d . . . . .
H33A H -0.122401 0.774346 0.366039 0.036 Uiso 1 1 calc R U . . .
H33B H -0.099958 0.922549 0.406707 0.036 Uiso 1 1 calc R U . . .
H33C H -0.039946 0.843922 0.498364 0.036 Uiso 1 1 calc R U . . .
C17 C 0.4072(5) -0.1783(4) 0.7564(4) 0.0229(10) Uani 1 1 d . . . . .
H17 H 0.483893 -0.209371 0.744994 0.027 Uiso 1 1 calc R U . . .
C11 C 0.9489(6) 0.6251(5) 0.1160(5) 0.0400(15) Uani 1 1 d . . . . .
H11A H 1.030359 0.624533 0.182364 0.060 Uiso 1 1 calc R U . . .
H11B H 0.969074 0.695964 0.084759 0.060 Uiso 1 1 calc R U . . .
H11C H 0.926981 0.547485 0.056941 0.060 Uiso 1 1 calc R U . . .
C20 C 0.1800(5) -0.0918(4) 0.7858(4) 0.0218(11) Uani 1 1 d . . . . .
H20 H 0.100839 -0.063064 0.794135 0.026 Uiso 1 1 calc R U . . .
C22 C 0.2007(6) -0.3271(4) 0.9493(4) 0.0295(12) Uani 1 1 d . . . . .
H22A H 0.193591 -0.399771 0.889376 0.044 Uiso 1 1 calc R U . . .
H22B H 0.141934 -0.349640 0.991715 0.044 Uiso 1 1 calc R U . . .
H22C H 0.297648 -0.298905 1.002215 0.044 Uiso 1 1 calc R U . . .
C49 C 0.5304(5) 0.4808(4) 0.9186(4) 0.0284(12) Uani 1 1 d . . . . .
H49A H 0.552575 0.470594 0.997840 0.034 Uiso 1 1 calc R U . . .
H49B H 0.564415 0.568798 0.921979 0.034 Uiso 1 1 calc R U . . .
C26 C 0.4342(5) 0.5333(4) 0.5169(3) 0.0155(9) Uani 1 1 d . . . . .
C13 C 0.6881(5) 0.0700(4) 0.6691(3) 0.0156(9) Uani 1 1 d . . . . .
C46 C 0.1074(5) 0.3425(4) 0.6819(4) 0.0203(10) Uani 1 1 d . . . . .
H46 H 0.111134 0.392719 0.752332 0.024 Uiso 1 1 calc R U . . .
C16 C 0.3678(4) -0.0783(4) 0.7126(4) 0.0156(9) Uani 1 1 d . . . . .
C18 C 0.2510(5) -0.0386(4) 0.7256(4) 0.0184(10) Uani 1 1 d . . . . .
H18 H 0.218978 0.026566 0.692295 0.022 Uiso 1 1 calc R U . . .
C44 C -0.0208(6) 0.2196(5) 0.4915(5) 0.0219(14) Uani 1 1 d . . . . .
H44 H -0.106109 0.182608 0.429588 0.026 Uiso 1 1 calc R U . . .
C55 C 0.8181(5) 0.1715(5) 0.9795(4) 0.0280(12) Uani 1 1 d . . . . .
H55 H 0.910416 0.157890 0.996023 0.034 Uiso 1 1 calc R U . . .
C23 C 0.8292(8) 0.5962(6) 0.6845(7) 0.046(2) Uani 1 1 d 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'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
O6 Eu1 O4 99.51(11) . . ?
O6 Eu1 O7 73.39(11) . . ?
O4 Eu1 O7 148.75(9) . . ?
O6 Eu1 O10 141.71(9) . . ?
O4 Eu1 O10 73.06(10) . . ?
O7 Eu1 O10 130.99(10) . . ?
O6 Eu1 O9 69.97(11) . . ?
O4 Eu1 O9 70.92(11) . . ?
O7 Eu1 O9 130.25(11) . . ?
O10 Eu1 O9 72.17(11) . . ?
O6 Eu1 O3 71.53(10) . . ?
O4 Eu1 O3 69.67(11) . . ?
O7 Eu1 O3 79.32(11) . . ?
O10 Eu1 O3 134.00(10) . . ?
O9 Eu1 O3 117.87(10) . . ?
O6 Eu1 N1 137.84(10) . . ?
O4 Eu1 N1 82.57(12) . . ?
O7 Eu1 N1 83.32(11) . . ?
O10 Eu1 N1 79.52(10) . . ?
O9 Eu1 N1 145.61(11) . . ?
O3 Eu1 N1 69.91(10) . . ?
O6 Eu1 N3 85.06(11) . . ?
O4 Eu1 N3 136.69(11) . . ?
O7 Eu1 N3 73.97(11) . . ?
O10 Eu1 N3 77.10(10) . . ?
O9 Eu1 N3 70.47(11) . . ?
O3 Eu1 N3 148.58(10) . . ?
N1 Eu1 N3 121.91(11) . . ?
O6 Eu1 N2 133.56(11) . . ?
O4 Eu1 N2 126.86(11) . . ?
O7 Eu1 N2 67.83(10) . . ?
O10 Eu1 N2 63.63(10) . . ?
O9 Eu1 N2 119.07(10) . . ?
O3 Eu1 N2 122.90(10) . . ?
N1 Eu1 N2 61.23(11) . . ?
N3 Eu1 N2 60.71(10) . . ?
C32 O11 C33 117.5(4) . . ?
C48 O2 C49 105.1(3) . . ?
C44 C45 C46 119.1(4) . . ?
C44 C45 H45 120.4 . . ?
C46 C45 H45 120.4 . . ?
C48 N3 C50 106.7(4) . . ?
C48 N3 Eu1 120.0(3) . . ?
C50 N3 Eu1 132.7(3) . . ?
C10 O5 C11 116.6(4) . . ?
C47 N2 C43 117.2(4) . . ?
C47 N2 Eu1 121.5(3) . . ?
C43 N2 Eu1 121.0(3) . . ?
C15 O7 Eu1 136.3(3) . . ?
N1 C40 C39 110.9(3) . . ?
N1 C40 C41 102.3(3) . . ?
C39 C40 C41 113.2(4) . . ?
N1 C40 H40 110.0 . . ?
C39 C40 H40 110.0 . . ?
C41 C40 H40 110.0 . . ?
C21 O8 C22 117.2(4) . . ?
O11 C32 C31 124.9(5) . . ?
O11 C32 C30 114.8(4) . . ?
C31 C32 C30 120.3(4) . . ?
N3 C48 O2 119.2(4) . . ?
N3 C48 C47 123.1(4) . . ?
O2 C48 C47 117.8(4) . . ?
C6 C5 C7 117.8(4) . . ?
C6 C5 C4 122.9(4) . . ?
C7 C5 C4 119.3(4) . . ?
C2 O3 Eu1 131.5(3) . . ?
N3 C50 C51 110.0(3) . . ?
N3 C50 C49 102.0(3) . . ?
C51 C50 C49 114.2(4) . . ?
N3 C50 H50 110.1 . . ?
C51 C50 H50 110.1 . . ?
C49 C50 H50 110.1 . . ?
C9 C7 C5 121.1(4) . . ?
C9 C7 H7 119.5 . . ?
C5 C7 H7 119.5 . . ?
C13 O6 Eu1 131.8(3) . . ?
C53 C51 C52 119.3(5) . . ?
C53 C51 C50 121.0(5) . . ?
C52 C51 C50 119.7(5) . . ?
C28 C30 C32 119.7(4) . . ?
C28 C30 H30 120.1 . . ?
C32 C30 H30 120.1 . . ?
O8 C21 C20 115.6(4) . . ?
O8 C21 C19 124.3(4) . . ?
C20 C21 C19 120.1(5) . . ?
C31 C29 C27 121.5(4) . . ?
C31 C29 H29 119.3 . . ?
C27 C29 H29 119.3 . . ?
O4 C4 C3 121.8(4) . . ?
O4 C4 C5 117.4(4) . . ?
C3 C4 C5 120.8(4) . . ?
C7 C9 C10 119.7(5) . . ?
C7 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
F12B C12 F12A 105.8(4) . . ?
F12B C12 F12C 107.4(3) . . ?
F12A C12 F12C 105.8(4) . . ?
F12B C12 C13 114.3(4) . . ?
F12A C12 C13 112.6(3) . . ?
F12C C12 C13 110.3(4) . . ?
N1 C42 O1 119.4(4) . . ?
N1 C42 C43 123.1(4) . . ?
O1 C42 C43 117.4(4) . . ?
C55 C56 C54 121.9(7) . . ?
C55 C56 H56 119.0 . . ?
C54 C56 H56 119.0 . . ?
C2 C3 C4 122.8(4) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
O5 C10 C8 125.1(4) . . ?
O5 C10 C9 114.2(4) . . ?
C8 C10 C9 120.7(4) . . ?
C42 N1 C40 105.6(4) . . ?
C42 N1 Eu1 121.3(3) . . ?
C40 N1 Eu1 133.1(3) . . ?
C4 O4 Eu1 138.3(3) . . ?
C35 C37 C39 120.6(5) . . ?
C35 C37 H37 119.7 . . ?
C39 C37 H37 119.7 . . ?
O3 C2 C3 130.1(4) . . ?
O3 C2 C1 111.5(4) . . ?
C3 C2 C1 118.4(4) . . ?
O1 C41 C40 103.5(3) . . ?
O1 C41 H41A 111.1 . . ?
C40 C41 H41A 111.1 . . ?
O1 C41 H41B 111.1 . . ?
C40 C41 H41B 111.1 . . ?
H41A C41 H41B 109.0 . . ?
C24 O9 Eu1 131.9(3) . . ?
O7 C15 C14 123.3(4) . . ?
O7 C15 C16 117.7(4) . . ?
C14 C15 C16 118.9(4) . . ?
N2 C47 C46 123.3(4) . . ?
N2 C47 C48 112.9(4) . . ?
C46 C47 C48 123.8(4) . . ?
C17 C19 C21 119.0(4) . . ?
C17 C19 H19 120.5 . . ?
C21 C19 H19 120.5 . . ?
C6 C8 C10 118.5(4) . . ?
C6 C8 H8 120.7 . . ?
C10 C8 H8 120.7 . . ?
C52 C54 C56 118.1(6) . . ?
C52 C54 H54 120.9 . . ?
C56 C54 H54 120.9 . . ?
C29 C27 C28 118.2(4) . . ?
C29 C27 C26 119.5(4) . . ?
C28 C27 C26 122.3(4) . . ?
C51 C53 C55 120.0(5) . . ?
C51 C53 H53 120.0 . . ?
C55 C53 H53 120.0 . . ?
N2 C43 C44 123.1(4) . . ?
N2 C43 C42 112.9(4) . . ?
C44 C43 C42 123.9(4) . . ?
C38 C39 C37 118.7(5) . . ?
C38 C39 C40 122.7(4) . . ?
C37 C39 C40 118.5(4) . . ?
C36 C34 C35 119.0(7) . . ?
C36 C34 H34 120.5 . . ?
C35 C34 H34 120.5 . . ?
C8 C6 C5 122.2(4) . . ?
C8 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C34 C36 C38 120.6(6) . . ?
C34 C36 H36 119.7 . . ?
C38 C36 H36 119.7 . . ?
C54 C52 C51 121.2(5) . . ?
C54 C52 H52 119.4 . . ?
C51 C52 H52 119.4 . . ?
C32 C31 C29 119.2(4) . . ?
C32 C31 H31 120.4 . . ?
C29 C31 H31 120.4 . . ?
C13 C14 C15 123.0(4) . . ?
C13 C14 H14 118.5 . . ?
C15 C14 H14 118.5 . . ?
C39 C38 C36 120.4(4) . . ?
C39 C38 H38 119.8 . . ?
C36 C38 H38 119.8 . . ?
C26 O10 Eu1 137.5(3) . . ?
C24 C25 C26 122.9(4) . . ?
C24 C25 H25 118.5 . . ?
C26 C25 H25 118.5 . . ?
F1C C1 F1B 106.1(4) . . ?
F1C C1 F1A 106.4(4) . . ?
F1B C1 F1A 106.9(4) . . ?
F1C C1 C2 111.9(4) . . ?
F1B C1 C2 114.0(4) . . ?
F1A C1 C2 111.1(4) . . ?
C30 C28 C27 121.0(4) . . ?
C30 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C37 C35 C34 120.7(5) . . ?
C37 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C42 O1 C41 103.1(3) . . ?
O9 C24 C25 130.4(4) . . ?
O9 C24 C23 112.7(4) . . ?
C25 C24 C23 116.9(4) . . ?
O11 C33 H33A 109.5 . . ?
O11 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O11 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C19 C17 C16 122.0(4) . . ?
C19 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
O5 C11 H11A 109.5 . . ?
O5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C18 C20 C21 119.2(5) . . ?
C18 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
O8 C22 H22A 109.5 . . ?
O8 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O8 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C49 C50 104.6(3) . . ?
O2 C49 H49A 110.8 . . ?
C50 C49 H49A 110.8 . . ?
O2 C49 H49B 110.8 . . ?
C50 C49 H49B 110.8 . . ?
H49A C49 H49B 108.9 . . ?
O10 C26 C25 123.8(4) . . ?
O10 C26 C27 117.6(4) . . ?
C25 C26 C27 118.5(4) . . ?
O6 C13 C14 130.4(4) . . ?
O6 C13 C12 113.0(4) . . ?
C14 C13 C12 116.6(4) . . ?
C47 C46 C45 118.1(4) . . ?
C47 C46 H46 120.9 . . ?
C45 C46 H46 120.9 . . ?
C17 C16 C18 117.9(4) . . ?
C17 C16 C15 122.9(4) . . ?
C18 C16 C15 119.0(4) . . ?
C20 C18 C16 121.7(4) . . ?
C20 C18 H18 119.2 . . ?
C16 C18 H18 119.2 . . ?
C45 C44 C43 119.0(5) . . ?
C45 C44 H44 120.5 . . ?
C43 C44 H44 120.5 . . ?
C56 C55 C53 119.5(5) . . ?
C56 C55 H55 120.2 . . ?
C53 C55 H55 120.2 . . ?
F23B C23 F23C 113.8(7) . . ?
F23D C23 F23E 109.2(10) . . ?
F23B C23 F23A 106.0(8) . . ?
F23C C23 F23A 99.9(7) . . ?
F23D C23 F23F 100.4(9) . . ?
F23E C23 F23F 107.1(9) . . ?
F23D C23 C24 120.1(7) . . ?
F23B C23 C24 117.1(7) . . ?
F23C C23 C24 112.9(6) . . ?
F23E C23 C24 113.1(9) . . ?
F23A C23 C24 105.0(6) . . ?
F23F C23 C24 105.3(6) . . ?
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
F23A C23 1.403(10) . ?
F23B C23 1.294(11) . ?
F23C C23 1.327(9) . ?
F23D C23 1.247(11) . ?
F23E C23 1.338(14) . ?
F23F C23 1.422(12) . ?
Eu1 O6 2.368(3) . ?
Eu1 O4 2.392(3) . ?
Eu1 O7 2.393(3) . ?
Eu1 O10 2.401(3) . ?
Eu1 O9 2.422(3) . ?
Eu1 O3 2.456(3) . ?
Eu1 N1 2.614(4) . ?
Eu1 N3 2.644(4) . ?
Eu1 N2 2.711(4) . ?
O11 C32 1.380(6) . ?
O11 C33 1.419(6) . ?
F12C C12 1.351(5) . ?
F1A C1 1.350(5) . ?
O2 C48 1.350(5) . ?
O2 C49 1.462(6) . ?
C45 C44 1.367(7) . ?
C45 C46 1.399(7) . ?
C45 H45 0.9500 . ?
N3 C48 1.286(6) . ?
N3 C50 1.499(5) . ?
O5 C10 1.381(6) . ?
O5 C11 1.447(6) . ?
N2 C47 1.343(5) . ?
N2 C43 1.344(5) . ?
O7 C15 1.269(5) . ?
C40 N1 1.486(5) . ?
C40 C39 1.521(7) . ?
C40 C41 1.531(6) . ?
C40 H40 1.0000 . ?
F1C C1 1.342(6) . ?
O8 C21 1.371(6) . ?
O8 C22 1.417(6) . ?
C32 C31 1.381(7) . ?
C32 C30 1.406(7) . ?
C48 C47 1.476(7) . ?
C5 C6 1.399(6) . ?
C5 C7 1.400(6) . ?
C5 C4 1.484(6) . ?
O3 C2 1.280(6) . ?
C50 C51 1.511(6) . ?
C50 C49 1.561(6) . ?
C50 H50 1.0000 . ?
C7 C9 1.372(7) . ?
C7 H7 0.9500 . ?
O6 C13 1.266(5) . ?
C51 C53 1.379(7) . ?
C51 C52 1.398(7) . ?
C30 C28 1.373(6) . ?
C30 H30 0.9500 . ?
C21 C20 1.390(7) . ?
C21 C19 1.399(6) . ?
C29 C31 1.391(6) . ?
C29 C27 1.394(6) . ?
C29 H29 0.9500 . ?
C4 O4 1.269(5) . ?
C4 C3 1.424(6) . ?
C9 C10 1.405(7) . ?
C9 H9 0.9500 . ?
C12 F12B 1.345(6) . ?
C12 F12A 1.347(5) . ?
C12 C13 1.538(6) . ?
C42 N1 1.274(6) . ?
C42 O1 1.357(5) . ?
C42 C43 1.486(6) . ?
C56 C55 1.368(9) . ?
C56 C54 1.385(9) . ?
C56 H56 0.9500 . ?
C3 C2 1.355(7) . ?
C3 H3 0.9500 . ?
C10 C8 1.384(7) . ?
C37 C35 1.381(7) . ?
C37 C39 1.409(6) . ?
C37 H37 0.9500 . ?
F1B C1 1.349(5) . ?
C2 C1 1.547(6) . ?
C41 O1 1.471(5) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
O9 C24 1.257(5) . ?
C15 C14 1.427(6) . ?
C15 C16 1.498(6) . ?
C47 C46 1.387(6) . ?
C19 C17 1.384(7) . ?
C19 H19 0.9500 . ?
C8 C6 1.382(6) . ?
C8 H8 0.9500 . ?
C54 C52 1.384(7) . ?
C54 H54 0.9500 . ?
C27 C28 1.403(6) . ?
C27 C26 1.493(6) . ?
C53 C55 1.398(7) . ?
C53 H53 0.9500 . ?
C43 C44 1.388(7) . ?
C39 C38 1.384(7) . ?
C34 C36 1.388(8) . ?
C34 C35 1.393(10) . ?
C34 H34 0.9500 . ?
C6 H6 0.9500 . ?
C36 C38 1.401(7) . ?
C36 H36 0.9500 . ?
C52 H52 0.9500 . ?
C31 H31 0.9500 . ?
C14 C13 1.374(6) . ?
C14 H14 0.9500 . ?
C38 H38 0.9500 . ?
O10 C26 1.258(5) . ?
C25 C24 1.389(6) . ?
C25 C26 1.418(6) . ?
C25 H25 0.9500 . ?
C28 H28 0.9500 . ?
C35 H35 0.9500 . ?
C24 C23 1.555(9) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C17 C16 1.386(6) . ?
C17 H17 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C20 C18 1.387(7) . ?
C20 H20 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C46 H46 0.9500 . ?
C16 C18 1.392(6) . ?
C18 H18 0.9500 . ?
C44 H44 0.9500 . ?
C55 H55 0.9500 . ?
