#------------------------------------------------------------------------------
#$Date: 2020-10-06 10:42:45 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257417 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/73/1557338.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_1557338
loop_
_publ_author_name
'Breen, Colum'
'Pal, Robert'
'Elsegood, Mark R. J.'
'Teat, Simon J.'
'Iza, Felipe'
'Wende, Kristian'
'Buckley, Benjamin R.'
'Butler, Stephen J.'
_publ_section_title
;
 Time-resolved luminescence detection of peroxynitrite using a
 reactivity-based lanthanide probe
;
_journal_issue                   12
_journal_name_full               'Chemical Science'
_journal_page_first              3164
_journal_page_last               3170
_journal_paper_doi               10.1039/C9SC06053G
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C31 H37 B Eu N5 O9, 8(H2 O)'
_chemical_formula_sum            'C31 H53 B Eu N5 O17'
_chemical_formula_weight         930.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-11-14 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.300(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2696(5)
_cell_length_b                   15.8873(6)
_cell_length_c                   18.2435(7)
_cell_measurement_reflns_used    9168
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.97
_cell_measurement_theta_min      3.07
_cell_volume                     3839.7(3)
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_collection       'Bruker APEX 2'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 with PHOTON 100 detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7288
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            159626
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.930
_diffrn_reflns_theta_max         36.004
_diffrn_reflns_theta_min         1.744
_diffrn_source                   'Advanced Light Source station 11.3.1'
_exptl_absorpt_coefficient_mu    1.815
_exptl_absorpt_correction_T_max  0.854
_exptl_absorpt_correction_T_min  0.713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2, Sheldrick, G.M., (2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             1912
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: water'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.889
_refine_diff_density_min         -1.034
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       0.00220(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     540
_refine_ls_number_reflns         16877
_refine_ls_number_restraints     96
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0267
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0296P)²+2.9825P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0694
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15100
_reflns_number_total             16877
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9sc06053g2.cif
_cod_data_source_block           Eu1
_cod_depositor_comments
;Adding full bibliography for 1557338.cif.

 Adding full bibliography for 1557338.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1557338
_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_min   0.713
_shelx_estimated_absorpt_t_max   0.854
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.18574(2) 0.44845(2) 0.31416(2) 0.00983(2) Uani 1 1 d . . . . .
N1 N 0.00531(9) 0.48358(8) 0.24942(6) 0.0143(2) Uani 1 1 d . . . . .
C1 C -0.07868(11) 0.46342(10) 0.29731(8) 0.0153(2) Uani 1 1 d . . . . .
H1A H -0.143479 0.464797 0.267596 0.018 Uiso 1 1 calc R U . . .
H1B H -0.081544 0.506854 0.336049 0.018 Uiso 1 1 calc R U . . .
C2 C -0.06553(11) 0.37772(10) 0.33285(8) 0.0159(2) Uani 1 1 d . . . . .
H2A H -0.120597 0.368143 0.366268 0.019 Uiso 1 1 calc R U . . .
H2B H -0.070294 0.333693 0.294399 0.019 Uiso 1 1 calc R U . . .
N2 N 0.03299(9) 0.37061(7) 0.37481(6) 0.01222(19) Uani 1 1 d . . . . .
C3 C 0.05786(11) 0.28061(9) 0.38858(8) 0.0148(2) Uani 1 1 d . . . . .
H3A H -0.004258 0.249890 0.399906 0.018 Uiso 1 1 calc R U . . .
H3B H 0.106211 0.276211 0.431809 0.018 Uiso 1 1 calc R U . . .
C4 C 0.10326(11) 0.24025(9) 0.32308(8) 0.0149(2) Uani 1 1 d . . . . .
H4A H 0.118683 0.180528 0.334431 0.018 Uiso 1 1 calc R U . . .
H4B H 0.053269 0.241708 0.280674 0.018 Uiso 1 1 calc R U . . .
N3 N 0.19696(9) 0.28339(8) 0.30289(6) 0.01282(19) Uani 1 1 d . . . . .
C5 C 0.22125(11) 0.25590(9) 0.22783(7) 0.0148(2) Uani 1 1 d . . . . .
H5A H 0.209572 0.194558 0.222948 0.018 Uiso 1 1 calc R U . . .
H5B H 0.293518 0.266781 0.220806 0.018 Uiso 1 1 calc R U . . .
C6 C 0.15768(12) 0.30148(9) 0.16907(8) 0.0162(2) Uani 1 1 d . . . . .
H6A H 0.178298 0.283774 0.120101 0.019 Uiso 1 1 calc R U . . .
H6B H 0.085888 0.286032 0.172839 0.019 Uiso 1 1 calc R U . . .
N4 N 0.16902(10) 0.39401(8) 0.17650(7) 0.0160(2) Uani 1 1 d . . . . .
C7 C 0.08335(14) 0.43673(10) 0.13538(8) 0.0215(3) Uani 1 1 d . . . . .
H7A H 0.068574 0.407336 0.088132 0.026 Uiso 1 1 calc R U . . .
H7B H 0.102755 0.495361 0.124406 0.026 Uiso 1 1 calc R U . . .
C8 C -0.01060(13) 0.43737(10) 0.17881(8) 0.0193(3) Uani 1 1 d . . . . .
H8A H -0.066499 0.464106 0.148989 0.023 Uiso 1 1 calc R U . . .
H8B H -0.030546 0.378670 0.188988 0.023 Uiso 1 1 calc R U . . .
C9 C 0.00071(12) 0.57538(10) 0.23436(8) 0.0169(2) Uani 1 1 d . . . . .
H9A H -0.069450 0.591248 0.218845 0.020 Uiso 1 1 calc R U . . .
H9B H 0.044119 0.588792 0.193577 0.020 Uiso 1 1 calc R U . . .
N5 N 0.11551(9) 0.59798(7) 0.33996(6) 0.01254(19) Uani 1 1 d . . . . .
C10 C 0.03491(11) 0.62569(9) 0.30089(8) 0.0148(2) Uani 1 1 d . . . . .
C11 C -0.01626(12) 0.70049(10) 0.31816(9) 0.0199(3) Uani 1 1 d . . . . .
H11 H -0.072736 0.718897 0.287994 0.024 Uiso 1 1 calc R U . . .
C12 C 0.01597(13) 0.74620(10) 0.37851(9) 0.0202(3) Uani 1 1 d . . . . .
H12 H -0.020263 0.794737 0.392238 0.024 Uiso 1 1 calc R U . . .
C13 C 0.10360(12) 0.72069(9) 0.42031(8) 0.0157(2) Uani 1 1 d . . . . .
C14 C 0.14350(13) 0.76577(9) 0.48236(8) 0.0188(3) Uani 1 1 d . . . . .
H14 H 0.110279 0.814785 0.498496 0.023 Uiso 1 1 calc R U . . .
C15 C 0.23030(13) 0.73821(9) 0.51893(8) 0.0188(3) Uani 1 1 d . . . . .
H15 H 0.255042 0.766865 0.561991 0.023 Uiso 1 1 calc R U . . .
C16 C 0.28385(12) 0.66783(9) 0.49379(8) 0.0165(2) Uani 1 1 d . . . . .
H16 H 0.345118 0.650871 0.519024 0.020 Uiso 1 1 calc R U . . .
C17 C 0.24734(11) 0.62382(8) 0.43279(7) 0.0130(2) Uani 1 1 d . . . . .
C18 C 0.15325(10) 0.64684(8) 0.39719(7) 0.0125(2) Uani 1 1 d . . . . .
O1 O 0.29577(8) 0.55927(6) 0.39975(6) 0.01358(18) Uani 1 1 d . . . . .
C19 C 0.39585(11) 0.53670(9) 0.43064(8) 0.0148(2) Uani 1 1 d . . . . .
H19A H 0.411904 0.478293 0.416419 0.018 Uiso 1 1 calc R U . . .
H19B H 0.396731 0.539294 0.484887 0.018 Uiso 1 1 calc R U . . .
C20 C 0.47436(10) 0.59580(9) 0.40345(8) 0.0135(2) Uani 1 1 d . . . . .
C21 C 0.49094(11) 0.59670(10) 0.32845(8) 0.0167(2) Uani 1 1 d . . . . .
H21 H 0.451066 0.562334 0.295511 0.020 Uiso 1 1 calc R U . . .
C22 C 0.56599(11) 0.64803(10) 0.30201(8) 0.0179(3) Uani 1 1 d . . . . .
H22 H 0.577124 0.647432 0.251034 0.021 Uiso 1 1 calc R U . . .
C23 C 0.62546(11) 0.70051(10) 0.34874(9) 0.0175(3) Uani 1 1 d . . . . .
C24 C 0.60755(12) 0.69883(10) 0.42365(9) 0.0178(3) Uani 1 1 d . . . . .
H24 H 0.646695 0.733677 0.456645 0.021 Uiso 1 1 calc R U . . .
C25 C 0.53326(11) 0.64693(9) 0.45086(8) 0.0164(2) Uani 1 1 d . . . . .
H25 H 0.522874 0.646530 0.501946 0.020 Uiso 1 1 calc R U . . .
B1 B 0.70877(14) 0.75894(12) 0.31732(11) 0.0220(3) Uani 1 1 d . . . . .
O2 O 0.73645(9) 0.74287(9) 0.24772(7) 0.0262(3) Uani 1 1 d D . . . .
H2 H 0.7769(17) 0.7764(14) 0.2307(14) 0.039 Uiso 1 1 d D U . . .
O3 O 0.75143(12) 0.82432(9) 0.35454(10) 0.0361(3) Uani 1 1 d D . . . .
H3 H 0.730(2) 0.8423(19) 0.3930(11) 0.054 Uiso 1 1 d D U . . .
C26 C 0.02875(10) 0.41369(9) 0.44602(7) 0.0135(2) Uani 1 1 d . . . . .
H26A H -0.014445 0.381161 0.478252 0.016 Uiso 1 1 calc R U . . .
H26B H -0.001677 0.470149 0.438459 0.016 Uiso 1 1 calc R U . . .
C27 C 0.13425(11) 0.42260(9) 0.48296(7) 0.0129(2) Uani 1 1 d . . . . .
O4 O 0.20747(8) 0.41701(7) 0.44080(6) 0.01418(18) Uani 1 1 d . . . . .
O5 O 0.14136(9) 0.43650(8) 0.55005(6) 0.0190(2) Uani 1 1 d . . . . .
C28 C 0.28353(11) 0.26048(9) 0.35337(8) 0.0143(2) Uani 1 1 d . . . . .
H28A H 0.304470 0.201931 0.343595 0.017 Uiso 1 1 calc R U . . .
H28B H 0.263420 0.263602 0.404726 0.017 Uiso 1 1 calc R U . . .
C29 C 0.37168(11) 0.32003(9) 0.34311(7) 0.0132(2) Uani 1 1 d . . . . .
O6 O 0.35056(8) 0.39161(6) 0.31476(6) 0.01443(18) Uani 1 1 d . . . . .
O7 O 0.45825(8) 0.29622(7) 0.36377(6) 0.0191(2) Uani 1 1 d . . . . .
C30 C 0.26423(14) 0.42094(10) 0.14483(9) 0.0212(3) Uani 1 1 d D U . . .
H30A H 0.251399 0.429859 0.091397 0.025 Uiso 0.552(4) 1 calc R U P A 1
H30B H 0.314518 0.375159 0.151576 0.025 Uiso 0.552(4) 1 calc R U P A 1
H30C H 0.260990 0.410792 0.091202 0.025 Uiso 0.448(4) 1 calc R U P A 2
H30D H 0.322168 0.389228 0.167546 0.025 Uiso 0.448(4) 1 calc R U P A 2
C31 C 0.3098(3) 0.50345(19) 0.17989(18) 0.0152(5) Uani 0.552(4) 1 d D U P A 1
O8 O 0.25618(10) 0.53696(7) 0.22764(6) 0.0190(2) Uani 1 1 d D U . . .
O9 O 0.38913(18) 0.53287(14) 0.15607(13) 0.0231(6) Uani 0.552(4) 1 d D U P A 1
C31X C 0.2757(3) 0.5138(2) 0.1609(2) 0.0162(7) Uani 0.448(4) 1 d D U P A 2
O9X O 0.3179(2) 0.55857(17) 0.11610(17) 0.0263(8) Uani 0.448(4) 1 d D U P A 2
O10 O 0.69449(13) 0.89458(9) 0.48375(10) 0.0362(3) Uani 1 1 d D . . . .
H10B H 0.7522(12) 0.893(2) 0.5038(15) 0.054 Uiso 1 1 d D U . . .
H10A H 0.6535(16) 0.916(2) 0.5092(14) 0.054 Uiso 1 1 d D U . . .
O11 O 0.47516(13) 0.14363(9) 0.44118(8) 0.0336(3) Uani 1 1 d D . . . .
H11A H 0.4290(17) 0.1389(17) 0.4690(14) 0.050 Uiso 1 1 d D U . . .
H11B H 0.476(2) 0.1901(12) 0.4212(14) 0.050 Uiso 1 1 d D U . . .
O12 O 0.63237(11) 0.35490(11) 0.30445(11) 0.0447(5) Uani 1 1 d D . . . .
H12A H 0.656(2) 0.3936(16) 0.3320(16) 0.067 Uiso 1 1 d D U . . .
H12B H 0.5807(17) 0.3385(19) 0.3254(16) 0.067 Uiso 1 1 d D U . . .
O13 O 0.30617(9) 0.51184(8) 0.61379(7) 0.0228(2) Uani 1 1 d D . . . .
H13B H 0.3406(16) 0.4709(12) 0.6313(13) 0.034 Uiso 1 1 d D U . . .
H13A H 0.2555(13) 0.4885(14) 0.5916(13) 0.034 Uiso 1 1 d D U . . .
O14 O 0.65733(13) 1.06341(9) 0.45719(8) 0.0311(3) Uani 1 1 d D . . . .
H14A H 0.688(2) 1.0779(16) 0.4214(12) 0.047 Uiso 1 1 d D U . . .
H14B H 0.661(2) 1.0117(9) 0.4616(15) 0.047 Uiso 1 1 d D U . . .
O15 O 0.76350(19) 1.09554(16) 0.33834(14) 0.0703(7) Uani 1 1 d D . . . .
H15B H 0.815(2) 1.115(3) 0.366(2) 0.105 Uiso 1 1 d D U . . .
H15A H 0.798(3) 1.055(2) 0.318(2) 0.105 Uiso 1 1 d D U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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'
B B 0.0017 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0115 0.0064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.0914 3.8479 '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
O8 Eu1 O4 138.79(4) . . ?
O8 Eu1 O6 80.09(4) . . ?
O4 Eu1 O6 81.62(4) . . ?
O8 Eu1 N5 74.67(4) . . ?
O4 Eu1 N5 92.34(4) . . ?
O6 Eu1 N5 133.45(4) . . ?
O8 Eu1 N3 121.13(4) . . ?
O4 Eu1 N3 82.06(4) . . ?
O6 Eu1 N3 64.16(4) . . ?
N5 Eu1 N3 160.75(4) . . ?
O8 Eu1 N4 64.77(4) . . ?
O4 Eu1 N4 148.71(4) . . ?
O6 Eu1 N4 84.65(4) . . ?
N5 Eu1 N4 117.20(4) . . ?
N3 Eu1 N4 66.66(4) . . ?
O8 Eu1 N1 87.65(4) . . ?
O4 Eu1 N1 122.19(4) . . ?
O6 Eu1 N1 152.63(4) . . ?
N5 Eu1 N1 64.39(4) . . ?
N3 Eu1 N1 103.12(4) . . ?
N4 Eu1 N1 67.98(4) . . ?
O8 Eu1 N2 153.85(4) . . ?
O4 Eu1 N2 63.25(4) . . ?
O6 Eu1 N2 123.04(4) . . ?
N5 Eu1 N2 93.41(4) . . ?
N3 Eu1 N2 67.59(4) . . ?
N4 Eu1 N2 102.54(4) . . ?
N1 Eu1 N2 66.21(4) . . ?
O8 Eu1 O1 77.12(4) . . ?
O4 Eu1 O1 62.94(3) . . ?
O6 Eu1 O1 77.23(3) . . ?
N5 Eu1 O1 59.47(3) . . ?
N3 Eu1 O1 131.12(3) . . ?
N4 Eu1 O1 140.06(4) . . ?
N1 Eu1 O1 123.85(3) . . ?
N2 Eu1 O1 117.21(3) . . ?
C9 N1 C8 108.81(11) . . ?
C9 N1 C1 107.19(11) . . ?
C8 N1 C1 109.16(12) . . ?
C9 N1 Eu1 108.29(9) . . ?
C8 N1 Eu1 111.06(9) . . ?
C1 N1 Eu1 112.21(8) . . ?
N1 C1 C2 111.89(12) . . ?
N1 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
N2 C2 C1 111.50(12) . . ?
N2 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N2 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C26 N2 C2 110.07(11) . . ?
C26 N2 C3 108.52(11) . . ?
C2 N2 C3 109.99(11) . . ?
C26 N2 Eu1 102.64(8) . . ?
C2 N2 Eu1 114.80(8) . . ?
C3 N2 Eu1 110.46(8) . . ?
N2 C3 C4 111.68(11) . . ?
N2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
N2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
N3 C4 C3 112.20(11) . . ?
N3 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
N3 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C28 N3 C4 111.36(11) . . ?
C28 N3 C5 107.42(11) . . ?
C4 N3 C5 108.74(11) . . ?
C28 N3 Eu1 104.01(8) . . ?
C4 N3 Eu1 112.84(8) . . ?
C5 N3 Eu1 112.30(8) . . ?
N3 C5 C6 111.73(11) . . ?
N3 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
N3 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
N4 C6 C5 111.15(12) . . ?
N4 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
N4 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C30 N4 C6 109.55(12) . . ?
C30 N4 C7 108.37(12) . . ?
C6 N4 C7 109.59(12) . . ?
C30 N4 Eu1 104.37(9) . . ?
C6 N4 Eu1 114.34(8) . . ?
C7 N4 Eu1 110.37(9) . . ?
N4 C7 C8 111.53(12) . . ?
N4 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
N4 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
N1 C8 C7 112.10(14) . . ?
N1 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N1 C9 C10 111.47(11) . . ?
N1 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C10 N5 C18 117.96(12) . . ?
C10 N5 Eu1 119.45(9) . . ?
C18 N5 Eu1 122.33(9) . . ?
N5 C10 C11 122.85(14) . . ?
N5 C10 C9 117.05(12) . . ?
C11 C10 C9 120.07(13) . . ?
C12 C11 C10 119.62(14) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 119.47(14) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C12 C13 C14 123.00(13) . . ?
C12 C13 C18 117.25(13) . . ?
C14 C13 C18 119.75(14) . . ?
C15 C14 C13 119.54(14) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 121.24(14) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 120.18(15) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
O1 C17 C16 125.71(13) . . ?
O1 C17 C18 114.45(12) . . ?
C16 C17 C18 119.80(13) . . ?
N5 C18 C13 122.52(13) . . ?
N5 C18 C17 118.32(12) . . ?
C13 C18 C17 119.12(13) . . ?
C17 O1 C19 117.05(11) . . ?
C17 O1 Eu1 119.17(8) . . ?
C19 O1 Eu1 120.63(8) . . ?
O1 C19 C20 110.56(11) . . ?
O1 C19 H19A 109.5 . . ?
C20 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
C25 C20 C21 119.17(13) . . ?
C25 C20 C19 122.17(13) . . ?
C21 C20 C19 118.61(13) . . ?
C22 C21 C20 120.01(14) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 121.69(14) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 H22 119.2 . . ?
C24 C23 C22 117.42(14) . . ?
C24 C23 B1 121.86(15) . . ?
C22 C23 B1 120.72(14) . . ?
C25 C24 C23 121.35(14) . . ?
C25 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
C20 C25 C24 120.35(13) . . ?
C20 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
O3 B1 O2 118.99(16) . . ?
O3 B1 C23 123.62(16) . . ?
O2 B1 C23 117.36(17) . . ?
B1 O2 H2 116.2(19) . . ?
B1 O3 H3 123(2) . . ?
N2 C26 C27 110.63(11) . . ?
N2 C26 H26A 109.5 . . ?
C27 C26 H26A 109.5 . . ?
N2 C26 H26B 109.5 . . ?
C27 C26 H26B 109.5 . . ?
H26A C26 H26B 108.1 . . ?
O5 C27 O4 126.08(14) . . ?
O5 C27 C26 117.88(13) . . ?
O4 C27 C26 116.01(12) . . ?
O5 C27 Eu1 155.77(11) . . ?
C26 C27 Eu1 80.16(7) . . ?
C27 O4 Eu1 121.31(9) . . ?
N3 C28 C29 110.22(11) . . ?
N3 C28 H28A 109.6 . . ?
C29 C28 H28A 109.6 . . ?
N3 C28 H28B 109.6 . . ?
C29 C28 H28B 109.6 . . ?
H28A C28 H28B 108.1 . . ?
O7 C29 O6 124.81(13) . . ?
O7 C29 C28 118.34(13) . . ?
O6 C29 C28 116.84(12) . . ?
O7 C29 Eu1 157.69(10) . . ?
C28 C29 Eu1 80.05(8) . . ?
C29 O6 Eu1 121.63(9) . . ?
N4 C30 C31X 106.58(18) . . ?
N4 C30 C31 113.59(15) . . ?
N4 C30 H30A 108.8 . . ?
C31 C30 H30A 108.8 . . ?
N4 C30 H30B 108.8 . . ?
C31 C30 H30B 108.8 . . ?
H30A C30 H30B 107.7 . . ?
N4 C30 H30C 110.4 . . ?
C31X C30 H30C 110.4 . . ?
N4 C30 H30D 110.4 . . ?
C31X C30 H30D 110.4 . . ?
H30C C30 H30D 108.6 . . ?
O9 C31 O8 126.5(3) . . ?
O9 C31 C30 118.9(2) . . ?
O8 C31 C30 114.4(2) . . ?
O9 C31 Eu1 149.3(3) . . ?
C30 C31 Eu1 83.04(12) . . ?
C31 O8 Eu1 118.00(15) . . ?
C31X O8 Eu1 124.34(18) . . ?
O9X C31X O8 124.9(3) . . ?
O9X C31X C30 118.5(3) . . ?
O8 C31X C30 115.5(3) . . ?
H10B O10 H10A 113(2) . . ?
H11A O11 H11B 112(2) . . ?
H12A O12 H12B 104(2) . . ?
H13B O13 H13A 103.8(19) . . ?
H14A O14 H14B 109(2) . . ?
H15B O15 H15A 95(2) . . ?
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 O8 2.3478(11) . ?
Eu1 O4 2.3650(10) . ?
Eu1 O6 2.3657(10) . ?
Eu1 N5 2.6046(12) . ?
Eu1 N3 2.6354(12) . ?
Eu1 N4 2.6534(12) . ?
Eu1 N1 2.6671(12) . ?
Eu1 N2 2.6684(12) . ?
Eu1 O1 2.7216(10) . ?
N1 C9 1.4846(19) . ?
N1 C8 1.4872(19) . ?
N1 C1 1.4901(19) . ?
C1 C2 1.514(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N2 1.4807(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N2 C26 1.4725(18) . ?
N2 C3 1.4855(18) . ?
C3 C4 1.512(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N3 1.4846(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
N3 C28 1.4760(19) . ?
N3 C5 1.4902(18) . ?
C5 C6 1.510(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N4 1.4832(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
N4 C30 1.482(2) . ?
N4 C7 1.489(2) . ?
C7 C8 1.515(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.502(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N5 C10 1.3258(18) . ?
N5 C18 1.3723(18) . ?
C10 C11 1.413(2) . ?
C11 C12 1.367(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.413(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.416(2) . ?
C13 C18 1.4213(19) . ?
C14 C15 1.369(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.415(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.378(2) . ?
C16 H16 0.9500 . ?
C17 O1 1.3685(17) . ?
C17 C18 1.422(2) . ?
O1 C19 1.4572(18) . ?
C19 C20 1.508(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C25 1.393(2) . ?
C20 C21 1.398(2) . ?
C21 C22 1.395(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.403(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.401(2) . ?
C23 B1 1.576(2) . ?
C24 C25 1.398(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
B1 O3 1.348(3) . ?
B1 O2 1.366(2) . ?
O2 H2 0.829(13) . ?
O3 H3 0.822(14) . ?
C26 C27 1.525(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 O5 1.2419(17) . ?
C27 O4 1.2766(17) . ?
C28 C29 1.524(2) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 O7 1.2469(18) . ?
C29 O6 1.2738(17) . ?
C30 C31X 1.511(4) . ?
C30 C31 1.565(3) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 H30C 0.9900 . ?
C30 H30D 0.9900 . ?
C31 O9 1.253(4) . ?
C31 O8 1.272(3) . ?
O8 C31X 1.312(4) . ?
C31X O9X 1.240(4) . ?
O10 H10B 0.829(13) . ?
O10 H10A 0.808(13) . ?
O11 H11A 0.821(13) . ?
O11 H11B 0.823(13) . ?
O12 H12A 0.845(14) . ?
O12 H12B 0.845(14) . ?
O13 H13B 0.847(13) . ?
O13 H13A 0.851(13) . ?
O14 H14A 0.819(13) . ?
O14 H14B 0.826(13) . ?
O15 H15B 0.877(14) . ?
O15 H15A 0.881(14) . ?
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
C1 H1B O5 0.99 2.44 3.3527(18) 153.3 3_566 yes
C4 H4A O9 0.99 2.35 3.317(3) 163.9 2_545 yes
C4 H4A O9X 0.99 2.28 3.244(3) 164.8 2_545 yes
C9 H9B O11 0.99 2.61 3.413(2) 138.7 2 yes
C11 H11 O2 0.95 2.62 3.519(2) 157.4 1_455 yes
C19 H19A O6 0.99 2.41 3.1619(18) 131.9 . yes
O2 H2 O12 0.829(13) 1.872(14) 2.7009(19) 178(3) 2_655 yes
O3 H3 O10 0.822(14) 1.936(15) 2.753(2) 173(3) . yes
C26 H26B O5 0.99 2.39 3.2838(19) 149.4 3_566 yes
C28 H28B O4 0.99 2.64 3.1515(18) 112.1 . yes
O10 H10B O9X 0.829(13) 2.31(2) 2.934(4) 132(2) 4_676 yes
O10 H10A O11 0.808(13) 2.19(3) 2.769(2) 129(3) 3_666 yes
O11 H11A O10 0.821(13) 1.968(15) 2.769(2) 165(3) 3_666 yes
O11 H11B O7 0.823(13) 1.992(14) 2.8081(18) 171(3) . yes
O12 H12A O13 0.845(14) 1.851(15) 2.6891(19) 172(3) 3_666 yes
O12 H12B O7 0.845(14) 1.927(14) 2.7689(19) 174(3) . yes
O13 H13A O5 0.851(13) 1.848(13) 2.6973(17) 176(3) . yes
O14 H14A O15 0.819(13) 1.888(14) 2.701(2) 172(3) . yes
O14 H14B O10 0.826(13) 1.952(15) 2.765(2) 168(3) . 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
C9 N1 C1 C2 -164.72(12) . . . . ?
C8 N1 C1 C2 77.59(14) . . . . ?
Eu1 N1 C1 C2 -45.96(13) . . . . ?
N1 C1 C2 N2 55.82(15) . . . . ?
C1 C2 N2 C26 78.42(14) . . . . ?
C1 C2 N2 C3 -162.06(11) . . . . ?
C1 C2 N2 Eu1 -36.77(14) . . . . ?
C26 N2 C3 C4 -157.60(12) . . . . ?
C2 N2 C3 C4 81.94(14) . . . . ?
Eu1 N2 C3 C4 -45.80(13) . . . . ?
N2 C3 C4 N3 58.87(16) . . . . ?
C3 C4 N3 C28 76.93(15) . . . . ?
C3 C4 N3 C5 -164.90(12) . . . . ?
C3 C4 N3 Eu1 -39.61(14) . . . . ?
C28 N3 C5 C6 -160.04(12) . . . . ?
C4 N3 C5 C6 79.32(14) . . . . ?
Eu1 N3 C5 C6 -46.28(13) . . . . ?
N3 C5 C6 N4 56.20(16) . . . . ?
C5 C6 N4 C30 79.55(15) . . . . ?
C5 C6 N4 C7 -161.68(12) . . . . ?
C5 C6 N4 Eu1 -37.17(14) . . . . ?
C30 N4 C7 C8 -160.39(13) . . . . ?
C6 N4 C7 C8 80.10(15) . . . . ?
Eu1 N4 C7 C8 -46.68(15) . . . . ?
C9 N1 C8 C7 77.82(15) . . . . ?
C1 N1 C8 C7 -165.52(12) . . . . ?
Eu1 N1 C8 C7 -41.28(14) . . . . ?
N4 C7 C8 N1 61.17(17) . . . . ?
C8 N1 C9 C10 -169.51(12) . . . . ?
C1 N1 C9 C10 72.57(15) . . . . ?
Eu1 N1 C9 C10 -48.69(13) . . . . ?
C18 N5 C10 C11 -3.5(2) . . . . ?
Eu1 N5 C10 C11 170.76(11) . . . . ?
C18 N5 C10 C9 174.44(12) . . . . ?
Eu1 N5 C10 C9 -11.31(16) . . . . ?
N1 C9 C10 N5 42.06(18) . . . . ?
N1 C9 C10 C11 -139.96(14) . . . . ?
N5 C10 C11 C12 -1.6(2) . . . . ?
C9 C10 C11 C12 -179.47(15) . . . . ?
C10 C11 C12 C13 3.7(2) . . . . ?
C11 C12 C13 C14 178.26(15) . . . . ?
C11 C12 C13 C18 -0.8(2) . . . . ?
C12 C13 C14 C15 -178.31(14) . . . . ?
C18 C13 C14 C15 0.8(2) . . . . ?
C13 C14 C15 C16 3.2(2) . . . . ?
C14 C15 C16 C17 -2.1(2) . . . . ?
C15 C16 C17 O1 174.48(13) . . . . ?
C15 C16 C17 C18 -3.0(2) . . . . ?
C10 N5 C18 C13 6.53(19) . . . . ?
Eu1 N5 C18 C13 -167.54(10) . . . . ?
C10 N5 C18 C17 -171.30(12) . . . . ?
Eu1 N5 C18 C17 14.62(16) . . . . ?
C12 C13 C18 N5 -4.4(2) . . . . ?
C14 C13 C18 N5 176.46(13) . . . . ?
C12 C13 C18 C17 173.41(13) . . . . ?
C14 C13 C18 C17 -5.7(2) . . . . ?
O1 C17 C18 N5 6.99(17) . . . . ?
C16 C17 C18 N5 -175.28(12) . . . . ?
O1 C17 C18 C13 -170.92(12) . . . . ?
C16 C17 C18 C13 6.81(19) . . . . ?
C16 C17 O1 C19 -1.78(19) . . . . ?
C18 C17 O1 C19 175.80(11) . . . . ?
C16 C17 O1 Eu1 158.31(11) . . . . ?
C18 C17 O1 Eu1 -24.11(14) . . . . ?
C17 O1 C19 C20 -80.99(15) . . . . ?
Eu1 O1 C19 C20 119.23(10) . . . . ?
O1 C19 C20 C25 118.30(15) . . . . ?
O1 C19 C20 C21 -64.19(17) . . . . ?
C25 C20 C21 C22 0.3(2) . . . . ?
C19 C20 C21 C22 -177.27(13) . . . . ?
C20 C21 C22 C23 -0.9(2) . . . . ?
C21 C22 C23 C24 0.8(2) . . . . ?
C21 C22 C23 B1 -179.10(14) . . . . ?
C22 C23 C24 C25 0.0(2) . . . . ?
B1 C23 C24 C25 179.81(14) . . . . ?
C21 C20 C25 C24 0.4(2) . . . . ?
C19 C20 C25 C24 177.88(14) . . . . ?
C23 C24 C25 C20 -0.5(2) . . . . ?
C24 C23 B1 O3 -16.2(3) . . . . ?
C22 C23 B1 O3 163.65(17) . . . . ?
C24 C23 B1 O2 165.55(15) . . . . ?
C22 C23 B1 O2 -14.6(2) . . . . ?
C2 N2 C26 C27 -168.44(11) . . . . ?
C3 N2 C26 C27 71.15(14) . . . . ?
Eu1 N2 C26 C27 -45.78(12) . . . . ?
N2 C26 C27 O5 -161.15(13) . . . . ?
N2 C26 C27 O4 20.55(17) . . . . ?
N2 C26 C27 Eu1 36.04(9) . . . . ?
O5 C27 O4 Eu1 -153.36(12) . . . . ?
C26 C27 O4 Eu1 24.78(16) . . . . ?
C4 N3 C28 C29 -166.75(11) . . . . ?
C5 N3 C28 C29 74.28(13) . . . . ?
Eu1 N3 C28 C29 -44.94(11) . . . . ?
N3 C28 C29 O7 -158.74(12) . . . . ?
N3 C28 C29 O6 22.31(17) . . . . ?
N3 C28 C29 Eu1 34.69(9) . . . . ?
O7 C29 O6 Eu1 -159.13(11) . . . . ?
C28 C29 O6 Eu1 19.76(16) . . . . ?
C6 N4 C30 C31X -174.6(2) . . . . ?
C7 N4 C30 C31X 65.9(2) . . . . ?
Eu1 N4 C30 C31X -51.8(2) . . . . ?
C6 N4 C30 C31 -152.9(2) . . . . ?
C7 N4 C30 C31 87.6(2) . . . . ?
Eu1 N4 C30 C31 -30.0(2) . . . . ?
N4 C30 C31 O9 -178.5(3) . . . . ?
N4 C30 C31 O8 -3.0(4) . . . . ?
N4 C30 C31 Eu1 24.27(17) . . . . ?
O9 C31 O8 Eu1 -141.1(3) . . . . ?
C30 C31 O8 Eu1 43.8(3) . . . . ?
Eu1 O8 C31X O9X -175.9(3) . . . . ?
Eu1 O8 C31X C30 -8.6(5) . . . . ?
N4 C30 C31X O9X -147.8(4) . . . . ?
N4 C30 C31X O8 44.0(4) . . . . ?
