#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:19:29 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301836 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/25/4302541.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_4302541
loop_
_publ_author_name
'Jean-Claude G. Bünzli'
'Nail M. Shavaleev'
'Rosario Scopelliti'
'Frédéric Gumy'
_publ_contact_author_address
;Ecole polytechnique fédérale de Lausanne
Institut des sciences et ingénierie chimiques
EPFL SB ISIC LCSL
BCH 1402 (Bât. BCH)
CH-1015 Lausanne
Switzerland
;
_publ_contact_author_email       jean-claude.bunzli@epfl.ch
_publ_contact_author_fax         '+41 21 693 98 25'
_publ_contact_author_name        'Jean-Claude Bünzli'
_publ_contact_author_phone       '+41 21 693 98 21'
_publ_section_title
;
Benzothiazole- and Benzoxazole-Substituted Pyridine-2-Carboxylates as
Efficient Sensitizers of Europium Luminescence
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6178
_journal_page_last               6191
_journal_paper_doi               10.1021/ic9005136
_journal_volume                  48
_journal_year                    2009
_chemical_formula_moiety         'C39 H25 Eu N6 O8 S3, C2 H6 O, H2 O'
_chemical_formula_sum            'C41 H33 Eu N6 O10 S3'
_chemical_formula_weight         1017.87
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                118.006(7)
_cell_angle_beta                 91.984(8)
_cell_angle_gamma                112.457(8)
_cell_formula_units_Z            2
_cell_length_a                   12.1822(16)
_cell_length_b                   14.6625(14)
_cell_length_c                   14.8430(14)
_cell_measurement_reflns_used    60
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.730
_cell_measurement_theta_min      13.438
_cell_volume                     2087.6(5)
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs, 1990-2000)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            49865
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    1.718
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10, G.M. Sheldrick, 2003'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.754
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     568
_refine_ls_number_reflns         9559
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0234
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0191P)²+2.2350P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0536
_refine_ls_wR_factor_ref         0.0555
_reflns_number_gt                8877
_reflns_number_total             9559
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic9005136_si_001_10.cif
_cod_data_source_block           '[Eu(LS)3(H2O)2)]'
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        2087.6(4)
_cod_database_code               4302541
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.290156(10) 0.158935(9) 0.395902(8) 0.01175(4) Uani 1 1 d . . .
S1 S 0.63082(5) 0.15513(5) 0.61123(5) 0.02165(12) Uani 1 1 d . . .
S2 S -0.04982(5) 0.13477(5) 0.15510(5) 0.01931(12) Uani 1 1 d . . .
S3 S 0.04034(6) -0.31995(5) 0.21562(5) 0.02487(13) Uani 1 1 d . . .
O1 O 0.12456(14) 0.16372(14) 0.47453(13) 0.0185(3) Uani 1 1 d . . .
O2 O 0.01509(16) 0.14792(15) 0.58962(15) 0.0261(4) Uani 1 1 d . . .
O3 O 0.41717(14) 0.35040(13) 0.53983(13) 0.0181(3) Uani 1 1 d . . .
O4 O 0.46897(15) 0.53905(13) 0.64340(13) 0.0221(4) Uani 1 1 d . . .
O5 O 0.31874(15) 0.01353(13) 0.25133(13) 0.0211(4) Uani 1 1 d . . .
O6 O 0.41403(17) 0.03277(15) 0.13109(14) 0.0272(4) Uani 1 1 d . . .
O7 O 0.41379(15) 0.23745(13) 0.29977(13) 0.0185(3) Uani 1 1 d D . .
H7A H 0.456(2) 0.3120(18) 0.316(2) 0.028 Uiso 1 1 d D . .
H7B H 0.421(3) 0.188(2) 0.2348(18) 0.028 Uiso 1 1 d D . .
O8 O 0.17124(16) -0.03782(14) 0.35580(13) 0.0208(4) Uani 1 1 d D . .
H8A H 0.190(3) -0.086(2) 0.303(2) 0.031 Uiso 1 1 d D . .
H8B H 0.101(2) -0.073(2) 0.372(2) 0.031 Uiso 1 1 d D . .
N1 N 0.30320(17) 0.14980(15) 0.56595(14) 0.0145(4) Uani 1 1 d . . .
N2 N 0.49474(16) 0.15805(15) 0.47408(15) 0.0147(4) Uani 1 1 d . . .
N3 N 0.24425(16) 0.31908(15) 0.40110(15) 0.0145(4) Uani 1 1 d . . .
N4 N 0.10519(17) 0.09330(15) 0.23639(15) 0.0151(4) Uani 1 1 d . . .
N5 N 0.24158(17) -0.21521(16) 0.14512(15) 0.0168(4) Uani 1 1 d . . .
N6 N 0.07366(18) -0.50214(16) 0.10076(16) 0.0200(4) Uani 1 1 d . . .
C1 C 0.1058(2) 0.15136(18) 0.55286(19) 0.0176(5) Uani 1 1 d . . .
C2 C 0.2061(2) 0.14262(19) 0.60739(18) 0.0179(5) Uani 1 1 d . . .
C3 C 0.1983(2) 0.1293(2) 0.6943(2) 0.0273(6) Uani 1 1 d . . .
H3 H 0.1286 0.1248 0.7220 0.033 Uiso 1 1 calc R . .
C4 C 0.2946(3) 0.1227(3) 0.7395(2) 0.0327(6) Uani 1 1 d . . .
H4 H 0.2916 0.1135 0.7988 0.039 Uiso 1 1 calc R . .
C5 C 0.3955(2) 0.1298(2) 0.6971(2) 0.0261(5) Uani 1 1 d . . .
H5 H 0.4624 0.1255 0.7267 0.031 Uiso 1 1 calc R . .
C6 C 0.3961(2) 0.14324(19) 0.61026(18) 0.0167(4) Uani 1 1 d . . .
C7 C 0.4981(2) 0.15175(18) 0.55927(17) 0.0156(4) Uani 1 1 d . . .
C8 C 0.6911(2) 0.1679(2) 0.51107(19) 0.0204(5) Uani 1 1 d . . .
C9 C 0.8062(2) 0.1773(2) 0.4940(2) 0.0283(6) Uani 1 1 d . . .
H9 H 0.8634 0.1783 0.5401 0.034 Uiso 1 1 calc R . .
C10 C 0.8336(2) 0.1852(3) 0.4078(2) 0.0311(6) Uani 1 1 d . . .
H10 H 0.9114 0.1925 0.3945 0.037 Uiso 1 1 calc R . .
C11 C 0.7485(2) 0.1827(2) 0.3394(2) 0.0271(6) Uani 1 1 d . . .
H11 H 0.7695 0.1874 0.2802 0.033 Uiso 1 1 calc R . .
C12 C 0.6342(2) 0.1733(2) 0.35641(19) 0.0203(5) Uani 1 1 d . . .
H12 H 0.5774 0.1716 0.3095 0.024 Uiso 1 1 calc R . .
C13 C 0.6043(2) 0.16633(19) 0.44406(18) 0.0163(4) Uani 1 1 d . . .
C14 C 0.4080(2) 0.44124(18) 0.56190(18) 0.0162(4) Uani 1 1 d . . .
C15 C 0.3134(2) 0.42844(18) 0.48185(18) 0.0167(4) Uani 1 1 d . . .
C16 C 0.2979(2) 0.5218(2) 0.4919(2) 0.0217(5) Uani 1 1 d . . .
H16 H 0.3482 0.5981 0.5499 0.026 Uiso 1 1 calc R . .
C17 C 0.2075(2) 0.5013(2) 0.4156(2) 0.0280(6) Uani 1 1 d . . .
H17 H 0.1955 0.5636 0.4202 0.034 Uiso 1 1 calc R . .
C18 C 0.1349(2) 0.3886(2) 0.3323(2) 0.0248(5) Uani 1 1 d . . .
H18 H 0.0721 0.3724 0.2794 0.030 Uiso 1 1 calc R . .
C19 C 0.1559(2) 0.29935(19) 0.32784(18) 0.0166(4) Uani 1 1 d . . .
C20 C 0.0814(2) 0.17651(19) 0.24417(17) 0.0158(4) Uani 1 1 d . . .
C21 C -0.0785(2) -0.00831(19) 0.10049(18) 0.0184(5) Uani 1 1 d . . .
C22 C -0.1790(2) -0.1077(2) 0.0182(2) 0.0249(5) Uani 1 1 d . . .
H22 H -0.2410 -0.1021 -0.0166 0.030 Uiso 1 1 calc R . .
C23 C -0.1841(2) -0.2140(2) -0.0103(2) 0.0259(5) Uani 1 1 d . . .
H23 H -0.2519 -0.2829 -0.0644 0.031 Uiso 1 1 calc R . .
C24 C -0.0903(2) -0.2215(2) 0.03977(19) 0.0223(5) Uani 1 1 d . . .
H24 H -0.0958 -0.2956 0.0181 0.027 Uiso 1 1 calc R . .
C25 C 0.0101(2) -0.12308(19) 0.12020(18) 0.0189(5) Uani 1 1 d . . .
H25 H 0.0738 -0.1291 0.1523 0.023 Uiso 1 1 calc R . .
C26 C 0.0150(2) -0.01441(19) 0.15272(17) 0.0160(4) Uani 1 1 d . . .
C27 C 0.3574(2) -0.0250(2) 0.17051(18) 0.0193(5) Uani 1 1 d . . .
C28 C 0.3327(2) -0.15089(19) 0.11999(18) 0.0180(5) Uani 1 1 d . . .
C29 C 0.4014(2) -0.1946(2) 0.05418(18) 0.0221(5) Uani 1 1 d . . .
H29 H 0.4645 -0.1468 0.0379 0.026 Uiso 1 1 calc R . .
C30 C 0.3753(2) -0.3106(2) 0.01267(19) 0.0247(5) Uani 1 1 d . . .
H30 H 0.4220 -0.3423 -0.0309 0.030 Uiso 1 1 calc R . .
C31 C 0.2804(2) -0.3783(2) 0.03609(19) 0.0228(5) Uani 1 1 d . . .
H31 H 0.2599 -0.4576 0.0079 0.027 Uiso 1 1 calc R . .
C32 C 0.2154(2) -0.32756(19) 0.10212(18) 0.0186(5) Uani 1 1 d . . .
C33 C 0.1134(2) -0.39321(19) 0.13159(18) 0.0193(5) Uani 1 1 d . . .
C34 C -0.0223(2) -0.5350(2) 0.14500(18) 0.0195(5) Uani 1 1 d . . .
C35 C -0.0898(2) -0.6470(2) 0.1266(2) 0.0234(5) Uani 1 1 d . . .
H35 H -0.0715 -0.7081 0.0810 0.028 Uiso 1 1 calc R . .
C36 C -0.1827(2) -0.6667(2) 0.1757(2) 0.0257(5) Uani 1 1 d . . .
H36 H -0.2285 -0.7422 0.1635 0.031 Uiso 1 1 calc R . .
C37 C -0.2111(3) -0.5774(2) 0.2435(2) 0.0315(6) Uani 1 1 d . . .
H37 H -0.2749 -0.5932 0.2770 0.038 Uiso 1 1 calc R . .
C38 C -0.1467(3) -0.4663(2) 0.2619(2) 0.0323(6) Uani 1 1 d . . .
H38 H -0.1658 -0.4058 0.3071 0.039 Uiso 1 1 calc R . .
C39 C -0.0530(2) -0.4467(2) 0.2115(2) 0.0235(5) Uani 1 1 d . . .
C40 C 0.6229(3) 0.4453(3) 0.7799(2) 0.0431(8) Uani 1 1 d . . .
H40A H 0.6012 0.4278 0.7075 0.065 Uiso 1 1 calc R . .
H40B H 0.6264 0.3789 0.7782 0.065 Uiso 1 1 calc R . .
H40C H 0.7034 0.5132 0.8185 0.065 Uiso 1 1 calc R . .
C41 C 0.5275(3) 0.4700(3) 0.8344(3) 0.0435(8) Uani 1 1 d . . .
H41A H 0.4458 0.4023 0.7939 0.052 Uiso 1 1 calc R . .
H41B H 0.5463 0.4822 0.9058 0.052 Uiso 1 1 calc R . .
O9 O 0.52327(19) 0.57020(18) 0.84383(15) 0.0371(5) Uani 1 1 d . . .
H9A H 0.5125 0.5621 0.7838 0.056 Uiso 1 1 calc R . .
O10 O 0.6495(2) 0.0445(2) 0.0818(2) 0.0519(6) Uani 1 1 d D . .
H10A H 0.560(3) 0.036(4) 0.095(3) 0.078 Uiso 1 1 d D . .
H10B H 0.622(4) 0.018(3) -0.001(2) 0.078 Uiso 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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Eu1 O1 134.50(6) . . ?
O5 Eu1 O3 136.59(6) . . ?
O1 Eu1 O3 88.29(6) . . ?
O5 Eu1 O8 63.96(6) . . ?
O1 Eu1 O8 75.35(6) . . ?
O3 Eu1 O8 141.65(6) . . ?
O5 Eu1 O7 69.10(5) . . ?
O1 Eu1 O7 141.07(5) . . ?
O3 Eu1 O7 81.02(6) . . ?
O8 Eu1 O7 132.32(6) . . ?
O5 Eu1 N3 127.68(6) . . ?
O1 Eu1 N3 71.48(6) . . ?
O3 Eu1 N3 64.10(6) . . ?
O8 Eu1 N3 136.76(6) . . ?
O7 Eu1 N3 70.16(6) . . ?
O5 Eu1 N1 114.63(6) . . ?
O1 Eu1 N1 64.29(6) . . ?
O3 Eu1 N1 72.73(6) . . ?
O8 Eu1 N1 68.92(6) . . ?
O7 Eu1 N1 143.26(6) . . ?
N3 Eu1 N1 117.68(6) . . ?
O5 Eu1 N2 74.15(6) . . ?
O1 Eu1 N2 126.10(6) . . ?
O3 Eu1 N2 73.19(5) . . ?
O8 Eu1 N2 88.67(6) . . ?
O7 Eu1 N2 86.37(6) . . ?
N3 Eu1 N2 133.52(6) . . ?
N1 Eu1 N2 61.92(6) . . ?
O5 Eu1 N4 79.63(6) . . ?
O1 Eu1 N4 76.01(6) . . ?
O3 Eu1 N4 126.73(5) . . ?
O8 Eu1 N4 83.13(6) . . ?
O7 Eu1 N4 80.80(6) . . ?
N3 Eu1 N4 62.63(6) . . ?
N1 Eu1 N4 135.68(6) . . ?
N2 Eu1 N4 153.51(6) . . ?
C8 S1 C7 89.06(11) . . ?
C21 S2 C20 89.14(11) . . ?
C39 S3 C33 88.88(12) . . ?
C1 O1 Eu1 127.09(14) . . ?
C14 O3 Eu1 127.26(14) . . ?
C27 O5 Eu1 154.14(15) . . ?
Eu1 O7 H7A 130.9(18) . . ?
Eu1 O7 H7B 120.1(17) . . ?
H7A O7 H7B 109(2) . . ?
Eu1 O8 H8A 110.3(19) . . ?
Eu1 O8 H8B 133.6(18) . . ?
H8A O8 H8B 114(2) . . ?
C2 N1 C6 118.3(2) . . ?
C2 N1 Eu1 117.13(14) . . ?
C6 N1 Eu1 124.35(15) . . ?
C7 N2 C13 109.87(18) . . ?
C7 N2 Eu1 116.78(14) . . ?
C13 N2 Eu1 133.33(14) . . ?
C19 N3 C15 118.50(19) . . ?
C19 N3 Eu1 123.81(14) . . ?
C15 N3 Eu1 117.69(14) . . ?
C20 N4 C26 109.77(18) . . ?
C20 N4 Eu1 115.49(14) . . ?
C26 N4 Eu1 134.03(14) . . ?
C28 N5 C32 117.5(2) . . ?
C33 N6 C34 109.6(2) . . ?
O2 C1 O1 126.3(2) . . ?
O2 C1 C2 117.5(2) . . ?
O1 C1 C2 116.2(2) . . ?
N1 C2 C3 122.6(2) . . ?
N1 C2 C1 114.8(2) . . ?
C3 C2 C1 122.6(2) . . ?
C4 C3 C2 118.7(2) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
N1 C6 C5 122.7(2) . . ?
N1 C6 C7 114.3(2) . . ?
C5 C6 C7 123.0(2) . . ?
N2 C7 C6 122.5(2) . . ?
N2 C7 S1 116.72(17) . . ?
C6 C7 S1 120.82(17) . . ?
C9 C8 C13 122.6(2) . . ?
C9 C8 S1 127.8(2) . . ?
C13 C8 S1 109.61(17) . . ?
C10 C9 C8 117.5(2) . . ?
C10 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
C9 C10 C11 121.0(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 121.4(2) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 118.8(2) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
N2 C13 C12 126.6(2) . . ?
N2 C13 C8 114.7(2) . . ?
C12 C13 C8 118.7(2) . . ?
O4 C14 O3 125.8(2) . . ?
O4 C14 C15 118.0(2) . . ?
O3 C14 C15 116.20(19) . . ?
N3 C15 C16 122.6(2) . . ?
N3 C15 C14 114.48(19) . . ?
C16 C15 C14 122.9(2) . . ?
C17 C16 C15 118.7(2) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 119.1(2) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C17 C18 C19 118.8(2) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
N3 C19 C18 122.2(2) . . ?
N3 C19 C20 114.96(19) . . ?
C18 C19 C20 122.8(2) . . ?
N4 C20 C19 122.91(19) . . ?
N4 C20 S2 116.65(16) . . ?
C19 C20 S2 120.32(16) . . ?
C22 C21 C26 122.3(2) . . ?
C22 C21 S2 127.77(19) . . ?
C26 C21 S2 109.93(16) . . ?
C23 C22 C21 117.4(2) . . ?
C23 C22 H22 121.3 . . ?
C21 C22 H22 121.3 . . ?
C22 C23 C24 121.0(2) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C25 C24 C23 121.6(2) . . ?
C25 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C24 C25 C26 118.3(2) . . ?
C24 C25 H25 120.9 . . ?
C26 C25 H25 120.9 . . ?
C25 C26 N4 126.1(2) . . ?
C25 C26 C21 119.4(2) . . ?
N4 C26 C21 114.5(2) . . ?
O6 C27 O5 124.9(2) . . ?
O6 C27 C28 119.6(2) . . ?
O5 C27 C28 115.6(2) . . ?
N5 C28 C29 123.1(2) . . ?
N5 C28 C27 115.1(2) . . ?
C29 C28 C27 121.8(2) . . ?
C28 C29 C30 118.6(2) . . ?
C28 C29 H29 120.7 . . ?
C30 C29 H29 120.7 . . ?
C31 C30 C29 118.9(2) . . ?
C31 C30 H30 120.5 . . ?
C29 C30 H30 120.5 . . ?
C30 C31 C32 118.7(2) . . ?
C30 C31 H31 120.7 . . ?
C32 C31 H31 120.7 . . ?
N5 C32 C31 123.1(2) . . ?
N5 C32 C33 114.6(2) . . ?
C31 C32 C33 122.3(2) . . ?
N6 C33 C32 125.2(2) . . ?
N6 C33 S3 116.81(19) . . ?
C32 C33 S3 118.00(17) . . ?
N6 C34 C35 125.4(2) . . ?
N6 C34 C39 115.5(2) . . ?
C35 C34 C39 119.1(2) . . ?
C36 C35 C34 119.0(2) . . ?
C36 C35 H35 120.5 . . ?
C34 C35 H35 120.5 . . ?
C35 C36 C37 121.4(2) . . ?
C35 C36 H36 119.3 . . ?
C37 C36 H36 119.3 . . ?
C38 C37 C36 120.6(3) . . ?
C38 C37 H37 119.7 . . ?
C36 C37 H37 119.7 . . ?
C37 C38 C39 117.8(3) . . ?
C37 C38 H38 121.1 . . ?
C39 C38 H38 121.1 . . ?
C38 C39 C34 122.0(2) . . ?
C38 C39 S3 128.8(2) . . ?
C34 C39 S3 109.20(19) . . ?
C41 C40 H40A 109.5 . . ?
C41 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C41 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
O9 C41 C40 111.6(3) . . ?
O9 C41 H41A 109.3 . . ?
C40 C41 H41A 109.3 . . ?
O9 C41 H41B 109.3 . . ?
C40 C41 H41B 109.3 . . ?
H41A C41 H41B 108.0 . . ?
C41 O9 H9A 109.5 . . ?
H10A O10 H10B 94(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 O5 2.3651(16) . ?
Eu1 O1 2.3729(16) . ?
Eu1 O3 2.3790(16) . ?
Eu1 O8 2.4311(16) . ?
Eu1 O7 2.4488(17) . ?
Eu1 N3 2.5823(18) . ?
Eu1 N1 2.5922(19) . ?
Eu1 N2 2.7197(18) . ?
Eu1 N4 2.7282(19) . ?
S1 C8 1.736(3) . ?
S1 C7 1.740(2) . ?
S2 C21 1.733(2) . ?
S2 C20 1.739(2) . ?
S3 C39 1.740(3) . ?
S3 C33 1.746(2) . ?
O1 C1 1.273(3) . ?
O2 C1 1.244(3) . ?
O3 C14 1.265(3) . ?
O4 C14 1.252(3) . ?
O5 C27 1.259(3) . ?
O6 C27 1.258(3) . ?
O7 H7A 0.92(2) . ?
O7 H7B 0.93(2) . ?
O8 H8A 0.89(2) . ?
O8 H8B 0.92(2) . ?
N1 C2 1.344(3) . ?
N1 C6 1.346(3) . ?
N2 C7 1.311(3) . ?
N2 C13 1.401(3) . ?
N3 C19 1.345(3) . ?
N3 C15 1.346(3) . ?
N4 C20 1.313(3) . ?
N4 C26 1.408(3) . ?
N5 C28 1.349(3) . ?
N5 C32 1.349(3) . ?
N6 C33 1.305(3) . ?
N6 C34 1.396(3) . ?
C1 C2 1.520(3) . ?
C2 C3 1.393(3) . ?
C3 C4 1.389(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.473(3) . ?
C8 C9 1.400(3) . ?
C8 C13 1.413(3) . ?
C9 C10 1.379(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.403(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.402(3) . ?
C12 H12 0.9500 . ?
C14 C15 1.519(3) . ?
C15 C16 1.393(3) . ?
C16 C17 1.389(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.400(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.477(3) . ?
C21 C22 1.406(3) . ?
C21 C26 1.410(3) . ?
C22 C23 1.384(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.409(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.392(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.407(3) . ?
C25 H25 0.9500 . ?
C27 C28 1.524(3) . ?
C28 C29 1.395(3) . ?
C29 C30 1.400(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.385(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.400(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.477(3) . ?
C34 C35 1.408(3) . ?
C34 C39 1.408(3) . ?
C35 C36 1.379(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.407(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.391(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.398(4) . ?
C38 H38 0.9500 . ?
C40 C41 1.500(5) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 O9 1.430(4) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
O9 H9A 0.8400 . ?
O10 H10A 1.08(2) . ?
O10 H10B 1.09(2) . ?
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
O7 H7A O4 0.92(2) 1.78(2) 2.690(2) 174(3) 2_666
O7 H7B O6 0.93(2) 2.03(2) 2.868(2) 150(2) .
O8 H8A N5 0.89(2) 2.51(2) 3.395(3) 175(3) .
O8 H8A S3 0.89(2) 2.77(3) 3.2608(18) 117(2) .
O8 H8B O2 0.92(2) 1.73(2) 2.640(2) 170(3) 2_556
O9 H9A O4 0.84 1.97 2.802(3) 173.9 .
O10 H10A O6 1.08(2) 1.87(2) 2.946(3) 175(4) .
O10 H10B O6 1.09(2) 1.68(2) 2.768(3) 174(4) 2_655
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
O5 Eu1 O1 C1 94.23(19) . . . . ?
O3 Eu1 O1 C1 -77.49(18) . . . . ?
O8 Eu1 O1 C1 67.47(17) . . . . ?
O7 Eu1 O1 C1 -150.90(16) . . . . ?
N3 Eu1 O1 C1 -140.69(18) . . . . ?
N1 Eu1 O1 C1 -5.87(17) . . . . ?
N2 Eu1 O1 C1 -9.8(2) . . . . ?
N4 Eu1 O1 C1 153.90(18) . . . . ?
O5 Eu1 O3 C14 122.35(18) . . . . ?
O1 Eu1 O3 C14 -66.24(19) . . . . ?
O8 Eu1 O3 C14 -129.79(18) . . . . ?
O7 Eu1 O3 C14 76.20(19) . . . . ?
N3 Eu1 O3 C14 3.96(18) . . . . ?
N1 Eu1 O3 C14 -129.8(2) . . . . ?
N2 Eu1 O3 C14 165.1(2) . . . . ?
N4 Eu1 O3 C14 4.9(2) . . . . ?
O1 Eu1 O5 C27 139.4(3) . . . . ?
O3 Eu1 O5 C27 -52.6(4) . . . . ?
O8 Eu1 O5 C27 168.4(4) . . . . ?
O7 Eu1 O5 C27 -3.0(4) . . . . ?
N3 Eu1 O5 C27 38.1(4) . . . . ?
N1 Eu1 O5 C27 -143.2(4) . . . . ?
N2 Eu1 O5 C27 -95.1(4) . . . . ?
N4 Eu1 O5 C27 81.1(4) . . . . ?
O5 Eu1 N1 C2 -124.03(15) . . . . ?
O1 Eu1 N1 C2 5.39(14) . . . . ?
O3 Eu1 N1 C2 102.00(16) . . . . ?
O8 Eu1 N1 C2 -77.99(16) . . . . ?
O7 Eu1 N1 C2 148.37(14) . . . . ?
N3 Eu1 N1 C2 54.81(17) . . . . ?
N2 Eu1 N1 C2 -178.22(17) . . . . ?
N4 Eu1 N1 C2 -23.31(19) . . . . ?
O5 Eu1 N1 C6 50.87(18) . . . . ?
O1 Eu1 N1 C6 -179.71(18) . . . . ?
O3 Eu1 N1 C6 -83.11(17) . . . . ?
O8 Eu1 N1 C6 96.90(17) . . . . ?
O7 Eu1 N1 C6 -36.7(2) . . . . ?
N3 Eu1 N1 C6 -130.29(16) . . . . ?
N2 Eu1 N1 C6 -3.32(16) . . . . ?
N4 Eu1 N1 C6 151.59(15) . . . . ?
O5 Eu1 N2 C7 -129.05(16) . . . . ?
O1 Eu1 N2 C7 4.96(17) . . . . ?
O3 Eu1 N2 C7 79.96(15) . . . . ?
O8 Eu1 N2 C7 -65.78(15) . . . . ?
O7 Eu1 N2 C7 161.66(15) . . . . ?
N3 Eu1 N2 C7 103.60(16) . . . . ?
N1 Eu1 N2 C7 0.93(14) . . . . ?
N4 Eu1 N2 C7 -137.44(16) . . . . ?
O5 Eu1 N2 C13 53.08(18) . . . . ?
O1 Eu1 N2 C13 -172.91(17) . . . . ?
O3 Eu1 N2 C13 -97.92(19) . . . . ?
O8 Eu1 N2 C13 116.35(19) . . . . ?
O7 Eu1 N2 C13 -16.21(18) . . . . ?
N3 Eu1 N2 C13 -74.3(2) . . . . ?
N1 Eu1 N2 C13 -176.9(2) . . . . ?
N4 Eu1 N2 C13 44.7(2) . . . . ?
O5 Eu1 N3 C19 48.98(19) . . . . ?
O1 Eu1 N3 C19 -83.50(18) . . . . ?
O3 Eu1 N3 C19 179.17(19) . . . . ?
O8 Eu1 N3 C19 -41.7(2) . . . . ?
O7 Eu1 N3 C19 89.70(18) . . . . ?
N1 Eu1 N3 C19 -129.69(17) . . . . ?
N2 Eu1 N3 C19 153.91(16) . . . . ?
N4 Eu1 N3 C19 -0.03(16) . . . . ?
O5 Eu1 N3 C15 -130.77(16) . . . . ?
O1 Eu1 N3 C15 96.75(17) . . . . ?
O3 Eu1 N3 C15 -0.58(15) . . . . ?
O8 Eu1 N3 C15 138.55(15) . . . . ?
O7 Eu1 N3 C15 -90.05(16) . . . . ?
N1 Eu1 N3 C15 50.56(18) . . . . ?
N2 Eu1 N3 C15 -25.8(2) . . . . ?
N4 Eu1 N3 C15 -179.78(18) . . . . ?
O5 Eu1 N4 C20 -145.23(17) . . . . ?
O1 Eu1 N4 C20 73.51(16) . . . . ?
O3 Eu1 N4 C20 -3.53(19) . . . . ?
O8 Eu1 N4 C20 150.07(17) . . . . ?
O7 Eu1 N4 C20 -74.98(16) . . . . ?
N3 Eu1 N4 C20 -2.63(15) . . . . ?
N1 Eu1 N4 C20 100.00(17) . . . . ?
N2 Eu1 N4 C20 -137.02(16) . . . . ?
O5 Eu1 N4 C26 45.64(19) . . . . ?
O1 Eu1 N4 C26 -95.6(2) . . . . ?
O3 Eu1 N4 C26 -172.65(18) . . . . ?
O8 Eu1 N4 C26 -19.1(2) . . . . ?
O7 Eu1 N4 C26 115.9(2) . . . . ?
N3 Eu1 N4 C26 -171.7(2) . . . . ?
N1 Eu1 N4 C26 -69.1(2) . . . . ?
N2 Eu1 N4 C26 53.9(3) . . . . ?
Eu1 O1 C1 O2 -175.87(17) . . . . ?
Eu1 O1 C1 C2 5.5(3) . . . . ?
C6 N1 C2 C3 0.3(3) . . . . ?
Eu1 N1 C2 C3 175.53(18) . . . . ?
C6 N1 C2 C1 179.74(18) . . . . ?
Eu1 N1 C2 C1 -5.0(2) . . . . ?
O2 C1 C2 N1 -178.4(2) . . . . ?
O1 C1 C2 N1 0.4(3) . . . . ?
O2 C1 C2 C3 1.0(3) . . . . ?
O1 C1 C2 C3 179.8(2) . . . . ?
N1 C2 C3 C4 -0.3(4) . . . . ?
C1 C2 C3 C4 -179.6(2) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C2 N1 C6 C5 -0.2(3) . . . . ?
Eu1 N1 C6 C5 -175.06(17) . . . . ?
C2 N1 C6 C7 179.89(19) . . . . ?
Eu1 N1 C6 C7 5.1(3) . . . . ?
C4 C5 C6 N1 0.1(4) . . . . ?
C4 C5 C6 C7 179.9(2) . . . . ?
C13 N2 C7 C6 179.50(19) . . . . ?
Eu1 N2 C7 C6 1.1(3) . . . . ?
C13 N2 C7 S1 0.0(2) . . . . ?
Eu1 N2 C7 S1 -178.32(9) . . . . ?
N1 C6 C7 N2 -3.9(3) . . . . ?
C5 C6 C7 N2 176.2(2) . . . . ?
N1 C6 C7 S1 175.50(15) . . . . ?
C5 C6 C7 S1 -4.4(3) . . . . ?
C8 S1 C7 N2 0.66(18) . . . . ?
C8 S1 C7 C6 -178.81(19) . . . . ?
C7 S1 C8 C9 179.5(2) . . . . ?
C7 S1 C8 C13 -1.12(18) . . . . ?
C13 C8 C9 C10 -0.1(4) . . . . ?
S1 C8 C9 C10 179.3(2) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C9 C10 C11 C12 0.7(4) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C7 N2 C13 C12 179.2(2) . . . . ?
Eu1 N2 C13 C12 -2.8(3) . . . . ?
C7 N2 C13 C8 -1.0(3) . . . . ?
Eu1 N2 C13 C8 177.02(15) . . . . ?
C11 C12 C13 N2 179.1(2) . . . . ?
C11 C12 C13 C8 -0.7(3) . . . . ?
C9 C8 C13 N2 -179.1(2) . . . . ?
S1 C8 C13 N2 1.4(3) . . . . ?
C9 C8 C13 C12 0.7(4) . . . . ?
S1 C8 C13 C12 -178.71(18) . . . . ?
Eu1 O3 C14 O4 173.05(17) . . . . ?
Eu1 O3 C14 C15 -6.4(3) . . . . ?
C19 N3 C15 C16 -0.6(3) . . . . ?
Eu1 N3 C15 C16 179.13(18) . . . . ?
C19 N3 C15 C14 178.4(2) . . . . ?
Eu1 N3 C15 C14 -1.9(2) . . . . ?
O4 C14 C15 N3 -174.5(2) . . . . ?
O3 C14 C15 N3 5.0(3) . . . . ?
O4 C14 C15 C16 4.5(3) . . . . ?
O3 C14 C15 C16 -176.0(2) . . . . ?
N3 C15 C16 C17 0.0(4) . . . . ?
C14 C15 C16 C17 -178.9(2) . . . . ?
C15 C16 C17 C18 0.6(4) . . . . ?
C16 C17 C18 C19 -0.4(4) . . . . ?
C15 N3 C19 C18 0.8(3) . . . . ?
Eu1 N3 C19 C18 -178.98(18) . . . . ?
C15 N3 C19 C20 -177.9(2) . . . . ?
Eu1 N3 C19 C20 2.4(3) . . . . ?
C17 C18 C19 N3 -0.2(4) . . . . ?
C17 C18 C19 C20 178.3(2) . . . . ?
C26 N4 C20 C19 176.9(2) . . . . ?
Eu1 N4 C20 C19 5.2(3) . . . . ?
C26 N4 C20 S2 0.9(3) . . . . ?
Eu1 N4 C20 S2 -170.83(10) . . . . ?
N3 C19 C20 N4 -5.2(3) . . . . ?
C18 C19 C20 N4 176.1(2) . . . . ?
N3 C19 C20 S2 170.68(17) . . . . ?
C18 C19 C20 S2 -8.0(3) . . . . ?
C21 S2 C20 N4 0.0(2) . . . . ?
C21 S2 C20 C19 -176.1(2) . . . . ?
C20 S2 C21 C22 177.8(2) . . . . ?
C20 S2 C21 C26 -0.94(18) . . . . ?
C26 C21 C22 C23 0.4(4) . . . . ?
S2 C21 C22 C23 -178.1(2) . . . . ?
C21 C22 C23 C24 -1.6(4) . . . . ?
C22 C23 C24 C25 0.6(4) . . . . ?
C23 C24 C25 C26 1.5(4) . . . . ?
C24 C25 C26 N4 176.1(2) . . . . ?
C24 C25 C26 C21 -2.6(3) . . . . ?
C20 N4 C26 C25 179.7(2) . . . . ?
Eu1 N4 C26 C25 -10.8(4) . . . . ?
C20 N4 C26 C21 -1.6(3) . . . . ?
Eu1 N4 C26 C21 167.94(15) . . . . ?
C22 C21 C26 C25 1.7(4) . . . . ?
S2 C21 C26 C25 -179.53(18) . . . . ?
C22 C21 C26 N4 -177.1(2) . . . . ?
S2 C21 C26 N4 1.7(3) . . . . ?
Eu1 O5 C27 O6 -1.5(5) . . . . ?
Eu1 O5 C27 C28 177.9(3) . . . . ?
C32 N5 C28 C29 -1.4(3) . . . . ?
C32 N5 C28 C27 179.68(19) . . . . ?
O6 C27 C28 N5 -160.4(2) . . . . ?
O5 C27 C28 N5 20.2(3) . . . . ?
O6 C27 C28 C29 20.7(3) . . . . ?
O5 C27 C28 C29 -158.8(2) . . . . ?
N5 C28 C29 C30 -0.4(4) . . . . ?
C27 C28 C29 C30 178.5(2) . . . . ?
C28 C29 C30 C31 1.7(4) . . . . ?
C29 C30 C31 C32 -1.1(4) . . . . ?
C28 N5 C32 C31 1.9(3) . . . . ?
C28 N5 C32 C33 -179.00(19) . . . . ?
C30 C31 C32 N5 -0.7(4) . . . . ?
C30 C31 C32 C33 -179.7(2) . . . . ?
C34 N6 C33 C32 179.1(2) . . . . ?
C34 N6 C33 S3 -0.1(2) . . . . ?
N5 C32 C33 N6 -178.9(2) . . . . ?
C31 C32 C33 N6 0.2(4) . . . . ?
N5 C32 C33 S3 0.3(3) . . . . ?
C31 C32 C33 S3 179.35(18) . . . . ?
C39 S3 C33 N6 0.69(19) . . . . ?
C39 S3 C33 C32 -178.54(19) . . . . ?
C33 N6 C34 C35 178.0(2) . . . . ?
C33 N6 C34 C39 -0.8(3) . . . . ?
N6 C34 C35 C36 -179.8(2) . . . . ?
C39 C34 C35 C36 -1.1(3) . . . . ?
C34 C35 C36 C37 0.0(4) . . . . ?
C35 C36 C37 C38 0.8(4) . . . . ?
C36 C37 C38 C39 -0.4(4) . . . . ?
C37 C38 C39 C34 -0.7(4) . . . . ?
C37 C38 C39 S3 178.1(2) . . . . ?
N6 C34 C39 C38 -179.7(2) . . . . ?
C35 C34 C39 C38 1.4(4) . . . . ?
N6 C34 C39 S3 1.3(3) . . . . ?
C35 C34 C39 S3 -177.57(18) . . . . ?
C33 S3 C39 C38 -180.0(3) . . . . ?
C33 S3 C39 C34 -1.04(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168336774
