#------------------------------------------------------------------------------
#$Date: 2019-11-24 08:11:58 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237248 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/80/4088078.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_4088078
loop_
_publ_author_name
'Bienfait, André M.'
'Wolf, Benjamin M.'
'Törnroos, Karl W.'
'Anwander, Reiner'
_publ_section_title
;
 Ln(II)/Pb(II)--Ln(III)/Pb(0) Redox Approach toward Rare-Earth-Metal
 Half-Sandwich Complexes
;
_journal_issue                   24
_journal_name_full               Organometallics
_journal_page_first              5734
_journal_paper_doi               10.1021/acs.organomet.5b00837
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C48 H84 Eu2 N8 O4'
_chemical_formula_sum            'C48 H84 Eu2 N8 O4'
_chemical_formula_weight         1141.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.4952(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.4307(5)
_cell_length_b                   13.7958(7)
_cell_length_c                   19.0532(10)
_cell_measurement_reflns_used    9850
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.04
_cell_measurement_theta_min      2.59
_cell_volume                     2654.5(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            43827
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.048
_diffrn_reflns_theta_min         1.843
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    2.388
_exptl_absorpt_correction_T_max  0.81800
_exptl_absorpt_correction_T_min  0.53854
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS-2014/3
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       'flat prism'
_exptl_crystal_F_000             1172
_exptl_crystal_size_max          0.417
_exptl_crystal_size_mid          0.396
_exptl_crystal_size_min          0.138
_refine_diff_density_max         2.776
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         7774
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.211
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0294
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0281P)²+5.5270P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0788
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7499
_reflns_number_total             7774
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om5b00837_si_002.cif
_cod_data_source_block           Compound4
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4088078
_shelx_shelxl_version_number     2014/7
_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'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.52226(2) 0.35879(2) 0.53144(2) 0.01505(4) Uani 1 1 d . . . . .
O1 O 0.3562(2) 0.22926(14) 0.46003(11) 0.0255(4) Uani 1 1 d . . . . .
N1 N 0.6439(2) 0.53862(15) 0.56960(11) 0.0172(4) Uani 1 1 d . . . . .
C1 C 0.3687(3) 0.1316(2) 0.48799(19) 0.0305(6) Uani 1 1 d . . . . .
H1A H 0.2862 0.1109 0.5004 0.037 Uiso 1 1 calc R U . . .
H1B H 0.4429 0.1270 0.5320 0.037 Uiso 1 1 calc R U . . .
O2 O 0.37712(19) 0.30130(15) 0.61460(11) 0.0252(4) Uani 1 1 d D . . . .
N2 N 0.5248(2) 0.54867(15) 0.58899(12) 0.0181(4) Uani 1 1 d . . . . .
C2 C 0.3953(3) 0.0695(2) 0.4278(2) 0.0353(7) Uani 1 1 d . . . . .
H2A H 0.3669 0.0016 0.4315 0.042 Uiso 1 1 calc R U . . .
H2B H 0.4901 0.0705 0.4276 0.042 Uiso 1 1 calc R U . . .
N3 N 0.6809(2) 0.22206(16) 0.58339(12) 0.0196(4) Uani 1 1 d . . . . .
C3 C 0.3102(4) 0.1196(3) 0.3615(2) 0.0429(8) Uani 1 1 d . . . . .
H3A H 0.2165 0.0992 0.3525 0.051 Uiso 1 1 calc R U . . .
H3B H 0.3424 0.1058 0.3179 0.051 Uiso 1 1 calc R U . . .
N4 N 0.6811(2) 0.22647(16) 0.51076(12) 0.0192(4) Uani 1 1 d . . . . .
C4 C 0.3265(4) 0.2263(2) 0.38193(17) 0.0331(6) Uani 1 1 d . . . . .
H4A H 0.3996 0.2553 0.3644 0.040 Uiso 1 1 calc R U . . .
H4B H 0.2440 0.2624 0.3605 0.040 Uiso 1 1 calc R U . . .
C5 C 0.4319(15) 0.248(2) 0.6806(13) 0.032(2) Uani 0.452(6) 1 d D . P A 1
H5A H 0.4557 0.2924 0.7227 0.038 Uiso 0.452(6) 1 calc R U P A 1
H5B H 0.5118 0.2116 0.6771 0.038 Uiso 0.452(6) 1 calc R U P A 1
C6 C 0.3224(9) 0.1794(6) 0.6878(5) 0.0380(11) Uani 0.452(6) 1 d D . P A 1
H6A H 0.3178 0.1219 0.6561 0.046 Uiso 0.452(6) 1 calc R U P A 1
H6B H 0.3334 0.1581 0.7385 0.046 Uiso 0.452(6) 1 calc R U P A 1
C7 C 0.2032(8) 0.2431(6) 0.6629(5) 0.0364(11) Uani 0.452(6) 1 d D . P A 1
H7A H 0.1897 0.2842 0.7031 0.044 Uiso 0.452(6) 1 calc R U P A 1
H7B H 0.1225 0.2039 0.6438 0.044 Uiso 0.452(6) 1 calc R U P A 1
C8 C 0.2351(11) 0.3043(18) 0.6038(10) 0.027(2) Uani 0.452(6) 1 d D . P A 1
H8A H 0.1906 0.2780 0.5555 0.032 Uiso 0.452(6) 1 calc R U P A 1
H8B H 0.2050 0.3718 0.6069 0.032 Uiso 0.452(6) 1 calc R U P A 1
C5A C 0.4132(12) 0.2352(18) 0.6747(11) 0.032(2) Uani 0.548(6) 1 d D . P A 2
H5A1 H 0.4799 0.2646 0.7154 0.038 Uiso 0.548(6) 1 calc R U P A 2
H5A2 H 0.4495 0.1743 0.6601 0.038 Uiso 0.548(6) 1 calc R U P A 2
C6A C 0.2839(7) 0.2165(5) 0.6959(4) 0.0380(11) Uani 0.548(6) 1 d D . P A 2
H6A1 H 0.2842 0.1516 0.7182 0.046 Uiso 0.548(6) 1 calc R U P A 2
H6A2 H 0.2686 0.2662 0.7304 0.046 Uiso 0.548(6) 1 calc R U P A 2
C7A C 0.1812(6) 0.2225(5) 0.6254(4) 0.0364(11) Uani 0.548(6) 1 d D . P A 2
H7A1 H 0.0930 0.2385 0.6329 0.044 Uiso 0.548(6) 1 calc R U P A 2
H7A2 H 0.1752 0.1611 0.5978 0.044 Uiso 0.548(6) 1 calc R U P A 2
C8A C 0.2340(9) 0.3040(14) 0.5876(7) 0.027(2) Uani 0.548(6) 1 d D . P A 2
H8A1 H 0.2083 0.2945 0.5344 0.032 Uiso 0.548(6) 1 calc R U P A 2
H8A2 H 0.1987 0.3671 0.5990 0.032 Uiso 0.548(6) 1 calc R U P A 2
C9 C 0.5403(3) 0.51038(19) 0.65561(14) 0.0210(5) Uani 1 1 d . . . . .
C10 C 0.6683(3) 0.4727(2) 0.67995(14) 0.0235(5) Uani 1 1 d . . . . .
H10A H 0.7090 0.4435 0.7284 0.028 Uiso 1 1 calc R U . . .
C11 C 0.7312(2) 0.49359(17) 0.62464(13) 0.0186(4) Uani 1 1 d . . . . .
C12 C 0.8740(3) 0.4790(2) 0.62236(15) 0.0234(5) Uani 1 1 d . . . . .
C13 C 0.8813(3) 0.4292(3) 0.55166(19) 0.0345(7) Uani 1 1 d . . . . .
H13A H 0.8470 0.3630 0.5509 0.052 Uiso 1 1 calc R U . . .
H13B H 0.9736 0.4273 0.5484 0.052 Uiso 1 1 calc R U . . .
H13C H 0.8279 0.4656 0.5104 0.052 Uiso 1 1 calc R U . . .
C14 C 0.9406(3) 0.5785(2) 0.6258(2) 0.0373(7) Uani 1 1 d . . . . .
H14A H 0.9372 0.6111 0.6711 0.056 Uiso 1 1 calc R U . . .
H14B H 0.8940 0.6178 0.5845 0.056 Uiso 1 1 calc R U . . .
H14C H 1.0331 0.5702 0.6242 0.056 Uiso 1 1 calc R U . . .
C15 C 0.9466(3) 0.4175(3) 0.6867(2) 0.0402(8) Uani 1 1 d . . . . .
H15A H 0.9026 0.3545 0.6850 0.060 Uiso 1 1 calc R U . . .
H15B H 0.9454 0.4507 0.7320 0.060 Uiso 1 1 calc R U . . .
H15C H 1.0385 0.4077 0.6843 0.060 Uiso 1 1 calc R U . . .
C16 C 0.4310(3) 0.5151(2) 0.69373(17) 0.0330(6) Uani 1 1 d . . . . .
H16A H 0.4519 0.5646 0.7318 0.050 Uiso 1 1 calc R U . . .
H16B H 0.4218 0.4520 0.7155 0.050 Uiso 1 1 calc R U . . .
H16C H 0.3477 0.5319 0.6588 0.050 Uiso 1 1 calc R U . . .
C17 C 0.7785(3) 0.16895(18) 0.50078(14) 0.0189(4) Uani 1 1 d . . . . .
C18 C 0.8437(3) 0.12607(19) 0.56676(15) 0.0222(5) Uani 1 1 d . . . . .
H18A H 0.9162 0.0822 0.5755 0.027 Uiso 1 1 calc R U . . .
C19 C 0.7784(3) 0.16217(18) 0.61683(14) 0.0196(4) Uani 1 1 d . . . . .
C20 C 0.8048(4) 0.1422(2) 0.69630(17) 0.0319(6) Uani 1 1 d . . . . .
H20A H 0.7531 0.1871 0.7182 0.048 Uiso 1 1 calc R U . . .
H20B H 0.8994 0.1511 0.7190 0.048 Uiso 1 1 calc R U . . .
H20C H 0.7793 0.0754 0.7038 0.048 Uiso 1 1 calc R U . . .
C21 C 0.8103(3) 0.1579(2) 0.42782(16) 0.0240(5) Uani 1 1 d . . . . .
C22 C 0.7196(5) 0.2192(3) 0.3706(2) 0.0534(12) Uani 1 1 d . . . . .
H22A H 0.6274 0.2005 0.3667 0.080 Uiso 1 1 calc R U . . .
H22B H 0.7408 0.2092 0.3239 0.080 Uiso 1 1 calc R U . . .
H22C H 0.7317 0.2877 0.3842 0.080 Uiso 1 1 calc R U . . .
C23 C 0.7956(4) 0.0514(2) 0.40421(19) 0.0362(7) Uani 1 1 d . . . . .
H23A H 0.7031 0.0313 0.3972 0.054 Uiso 1 1 calc R U . . .
H23B H 0.8524 0.0110 0.4417 0.054 Uiso 1 1 calc R U . . .
H23C H 0.8218 0.0437 0.3586 0.054 Uiso 1 1 calc R U . . .
C24 C 0.9555(4) 0.1862(3) 0.4354(2) 0.0473(9) Uani 1 1 d . . . . .
H24A H 0.9708 0.2519 0.4553 0.071 Uiso 1 1 calc R U . . .
H24B H 0.9750 0.1842 0.3877 0.071 Uiso 1 1 calc R U . . .
H24C H 1.0135 0.1406 0.4681 0.071 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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
N3 Eu1 N4 31.51(7) . .
N3 Eu1 N2 132.73(7) . 3_666
N4 Eu1 N2 101.75(7) . 3_666
N3 Eu1 O2 87.57(7) . .
N4 Eu1 O2 112.18(7) . .
N2 Eu1 O2 133.92(6) 3_666 .
N3 Eu1 O1 88.71(7) . .
N4 Eu1 O1 78.64(7) . .
N2 Eu1 O1 85.48(7) 3_666 .
O2 Eu1 O1 72.26(7) . .
N3 Eu1 N1 157.20(7) . 3_666
N4 Eu1 N1 126.77(7) . 3_666
N2 Eu1 N1 30.80(7) 3_666 3_666
O2 Eu1 N1 103.47(6) . 3_666
O1 Eu1 N1 76.12(6) . 3_666
N3 Eu1 N1 110.38(7) . .
N4 Eu1 N1 113.78(7) . .
N2 Eu1 N1 76.34(6) 3_666 .
O2 Eu1 N1 114.29(7) . .
O1 Eu1 N1 159.61(6) . .
N1 Eu1 N1 83.51(7) 3_666 .
N3 Eu1 N2 126.34(7) . .
N4 Eu1 N2 140.69(7) . .
N2 Eu1 N2 82.38(7) 3_666 .
O2 Eu1 N2 89.81(7) . .
O1 Eu1 N2 140.48(6) . .
N1 Eu1 N2 74.29(6) 3_666 .
N1 Eu1 N2 28.51(6) . .
N3 Eu1 C11 85.73(7) . .
N4 Eu1 C11 97.35(7) . .
N2 Eu1 C11 99.52(7) 3_666 .
O2 Eu1 C11 105.80(7) . .
O1 Eu1 C11 174.20(6) . .
N1 Eu1 C11 109.68(7) 3_666 .
N1 Eu1 C11 26.18(6) . .
N2 Eu1 C11 43.98(6) . .
N3 Eu1 C9 106.96(7) . .
N4 Eu1 C9 132.40(7) . .
N2 Eu1 C9 107.81(7) 3_666 .
O2 Eu1 C9 70.97(7) . .
O1 Eu1 C9 139.07(7) . .
N1 Eu1 C9 95.56(7) 3_666 .
N1 Eu1 C9 43.38(7) . .
N2 Eu1 C9 25.50(6) . .
C11 Eu1 C9 42.09(7) . .
N3 Eu1 C10 84.41(7) . .
N4 Eu1 C10 107.30(7) . .
N2 Eu1 C10 118.68(7) 3_666 .
O2 Eu1 C10 80.41(7) . .
O1 Eu1 C10 152.07(7) . .
N1 Eu1 C10 116.80(7) 3_666 .
N1 Eu1 C10 42.66(6) . .
N2 Eu1 C10 42.50(6) . .
C11 Eu1 C10 25.39(7) . .
C9 Eu1 C10 25.19(7) . .
N3 Eu1 Eu1 147.23(5) . 3_666
N4 Eu1 Eu1 131.90(5) . 3_666
N2 Eu1 Eu1 43.73(5) 3_666 3_666
O2 Eu1 Eu1 115.77(5) . 3_666
O1 Eu1 Eu1 119.23(5) . 3_666
N1 Eu1 Eu1 43.11(5) 3_666 3_666
N1 Eu1 Eu1 40.40(4) . 3_666
N2 Eu1 Eu1 38.65(4) . 3_666
C11 Eu1 Eu1 66.57(4) . 3_666
C9 Eu1 Eu1 64.10(5) . 3_666
C10 Eu1 Eu1 77.78(5) . 3_666
C1 O1 C4 109.3(2) . .
C1 O1 Eu1 117.25(17) . .
C4 O1 Eu1 119.87(18) . .
C11 N1 N2 108.2(2) . .
C11 N1 Eu1 174.92(17) . 3_666
N2 N1 Eu1 71.01(12) . 3_666
C11 N1 Eu1 88.16(14) . .
N2 N1 Eu1 77.30(12) . .
Eu1 N1 Eu1 96.49(6) 3_666 .
O1 C1 C2 105.5(3) . .
O1 C1 H1A 110.6 . .
C2 C1 H1A 110.6 . .
O1 C1 H1B 110.6 . .
C2 C1 H1B 110.6 . .
H1A C1 H1B 108.8 . .
C8 O2 C5 107.8(9) . .
C5A O2 C8A 109.8(6) . .
C5A O2 Eu1 127.4(7) . .
C8 O2 Eu1 130.0(5) . .
C5 O2 Eu1 121.8(8) . .
C8A O2 Eu1 119.0(4) . .
C9 N2 N1 107.9(2) . .
C9 N2 Eu1 171.83(18) . 3_666
N1 N2 Eu1 78.19(12) . 3_666
C9 N2 Eu1 89.40(15) . .
N1 N2 Eu1 74.19(12) . .
Eu1 N2 Eu1 97.62(7) 3_666 .
C1 C2 C3 101.1(3) . .
C1 C2 H2A 111.5 . .
C3 C2 H2A 111.5 . .
C1 C2 H2B 111.5 . .
C3 C2 H2B 111.5 . .
H2A C2 H2B 109.4 . .
C19 N3 N4 108.1(2) . .
C19 N3 Eu1 170.03(19) . .
N4 N3 Eu1 75.04(13) . .
C2 C3 C4 102.9(3) . .
C2 C3 H3A 111.2 . .
C4 C3 H3A 111.2 . .
C2 C3 H3B 111.2 . .
C4 C3 H3B 111.2 . .
H3A C3 H3B 109.1 . .
C17 N4 N3 107.8(2) . .
C17 N4 Eu1 170.66(18) . .
N3 N4 Eu1 73.45(13) . .
O1 C4 C3 105.8(3) . .
O1 C4 H4A 110.6 . .
C3 C4 H4A 110.6 . .
O1 C4 H4B 110.6 . .
C3 C4 H4B 110.6 . .
H4A C4 H4B 108.7 . .
O2 C5 C6 104.7(10) . .
O2 C5 H5A 110.8 . .
C6 C5 H5A 110.8 . .
O2 C5 H5B 110.8 . .
C6 C5 H5B 110.8 . .
H5A C5 H5B 108.9 . .
C7 C6 C5 100.9(11) . .
C7 C6 H6A 111.6 . .
C5 C6 H6A 111.6 . .
C7 C6 H6B 111.6 . .
C5 C6 H6B 111.6 . .
H6A C6 H6B 109.4 . .
C6 C7 C8 104.0(8) . .
C6 C7 H7A 110.9 . .
C8 C7 H7A 110.9 . .
C6 C7 H7B 110.9 . .
C8 C7 H7B 110.9 . .
H7A C7 H7B 109.0 . .
O2 C8 C7 106.7(9) . .
O2 C8 H8A 110.4 . .
C7 C8 H8A 110.4 . .
O2 C8 H8B 110.4 . .
C7 C8 H8B 110.4 . .
H8A C8 H8B 108.6 . .
O2 C5A C6A 104.2(9) . .
O2 C5A H5A1 110.9 . .
C6A C5A H5A1 110.9 . .
O2 C5A H5A2 110.9 . .
C6A C5A H5A2 110.9 . .
H5A1 C5A H5A2 108.9 . .
C7A C6A C5A 103.6(7) . .
C7A C6A H6A1 111.0 . .
C5A C6A H6A1 111.0 . .
C7A C6A H6A2 111.0 . .
C5A C6A H6A2 111.0 . .
H6A1 C6A H6A2 109.0 . .
C6A C7A C8A 101.8(6) . .
C6A C7A H7A1 111.4 . .
C8A C7A H7A1 111.4 . .
C6A C7A H7A2 111.4 . .
C8A C7A H7A2 111.4 . .
H7A1 C7A H7A2 109.3 . .
O2 C8A C7A 106.1(8) . .
O2 C8A H8A1 110.5 . .
C7A C8A H8A1 110.5 . .
O2 C8A H8A2 110.5 . .
C7A C8A H8A2 110.5 . .
H8A1 C8A H8A2 108.7 . .
N2 C9 C10 109.7(2) . .
N2 C9 C16 120.9(3) . .
C10 C9 C16 129.3(3) . .
N2 C9 Eu1 65.10(13) . .
C10 C9 Eu1 82.76(15) . .
C16 C9 Eu1 119.13(19) . .
C9 C10 C11 105.1(2) . .
C9 C10 Eu1 72.05(15) . .
C11 C10 Eu1 69.65(14) . .
C9 C10 H10A 127.3 . .
C11 C10 H10A 127.3 . .
Eu1 C10 H10A 127.3 . .
N1 C11 C10 109.0(2) . .
N1 C11 C12 120.9(2) . .
C10 C11 C12 130.0(2) . .
N1 C11 Eu1 65.66(13) . .
C10 C11 Eu1 84.96(16) . .
C12 C11 Eu1 117.64(16) . .
C11 C12 C15 110.2(2) . .
C11 C12 C13 110.5(2) . .
C15 C12 C13 109.4(3) . .
C11 C12 C14 108.6(2) . .
C15 C12 C14 109.6(3) . .
C13 C12 C14 108.6(3) . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C12 C14 H14A 109.5 . .
C12 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C12 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C12 C15 H15A 109.5 . .
C12 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C12 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C9 C16 H16A 109.5 . .
C9 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C9 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
N4 C17 C18 109.7(2) . .
N4 C17 C21 122.5(2) . .
C18 C17 C21 127.7(2) . .
C19 C18 C17 104.6(2) . .
C19 C18 H18A 127.7 . .
C17 C18 H18A 127.7 . .
N3 C19 C18 109.7(2) . .
N3 C19 C20 121.3(2) . .
C18 C19 C20 129.0(2) . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C22 C21 C17 111.3(2) . .
C22 C21 C23 109.0(3) . .
C17 C21 C23 109.7(2) . .
C22 C21 C24 110.5(3) . .
C17 C21 C24 109.0(3) . .
C23 C21 C24 107.2(3) . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C21 C23 H23A 109.5 . .
C21 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C21 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C21 C24 H24A 109.5 . .
C21 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C21 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Eu1 N3 2.541(2) .
Eu1 N4 2.561(2) .
Eu1 N2 2.564(2) 3_666
Eu1 O2 2.5753(19) .
Eu1 O1 2.620(2) .
Eu1 N1 2.654(2) 3_666
Eu1 N1 2.798(2) .
Eu1 N2 2.837(2) .
Eu1 C11 3.070(2) .
Eu1 C9 3.128(3) .
Eu1 C10 3.261(3) .
Eu1 Eu1 4.0684(3) 3_666
O1 C1 1.442(3) .
O1 C4 1.443(4) .
N1 C11 1.355(3) .
N1 N2 1.388(3) .
N1 Eu1 2.654(2) 3_666
C1 C2 1.512(5) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
O2 C5A 1.439(10) .
O2 C8 1.444(11) .
O2 C5 1.445(12) .
O2 C8A 1.453(10) .
N2 C9 1.347(3) .
N2 Eu1 2.564(2) 3_666
C2 C3 1.516(5) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
N3 C19 1.341(3) .
N3 N4 1.385(3) .
C3 C4 1.521(5) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
N4 C17 1.340(3) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.515(15) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C7 1.499(11) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.509(12) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C5A C6A 1.523(14) .
C5A H5A1 0.9900 .
C5A H5A2 0.9900 .
C6A C7A 1.497(9) .
C6A H6A1 0.9900 .
C6A H6A2 0.9900 .
C7A C8A 1.512(12) .
C7A H7A1 0.9900 .
C7A H7A2 0.9900 .
C8A H8A1 0.9900 .
C8A H8A2 0.9900 .
C9 C10 1.399(4) .
C9 C16 1.499(4) .
C10 C11 1.404(4) .
C10 H10A 1.0000 .
C11 C12 1.515(4) .
C12 C15 1.527(4) .
C12 C13 1.531(4) .
C12 C14 1.532(4) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 C18 1.402(4) .
C17 C21 1.516(4) .
C18 C19 1.396(4) .
C18 H18A 0.9500 .
C19 C20 1.495(4) .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 C22 1.511(5) .
C21 C23 1.534(4) .
C21 C24 1.535(5) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
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_4
C4 O1 C1 C2 20.2(3) . .
Eu1 O1 C1 C2 -120.6(2) . .
C11 N1 N2 C9 0.3(3) . .
Eu1 N1 N2 C9 -174.37(19) 3_666 .
Eu1 N1 N2 C9 84.08(17) . .
C11 N1 N2 Eu1 174.71(18) . 3_666
Eu1 N1 N2 Eu1 -101.54(5) . 3_666
C11 N1 N2 Eu1 -83.75(17) . .
Eu1 N1 N2 Eu1 101.54(5) 3_666 .
O1 C1 C2 C3 -36.0(3) . .
C1 C2 C3 C4 37.8(4) . .
C19 N3 N4 C17 0.2(3) . .
Eu1 N3 N4 C17 170.32(19) . .
C19 N3 N4 Eu1 -170.1(2) . .
C1 O1 C4 C3 4.4(4) . .
Eu1 O1 C4 C3 143.9(2) . .
C2 C3 C4 O1 -26.8(4) . .
C8 O2 C5 C6 28(3) . .
Eu1 O2 C5 C6 -146.6(11) . .
O2 C5 C6 C7 -39(2) . .
C5 C6 C7 C8 35.6(18) . .
C5 O2 C8 C7 -5(2) . .
Eu1 O2 C8 C7 168.9(6) . .
C6 C7 C8 O2 -20.2(18) . .
C8A O2 C5A C6A -14(2) . .
Eu1 O2 C5A C6A -171.7(7) . .
O2 C5A C6A C7A 32.6(18) . .
C5A C6A C7A C8A -37.7(14) . .
C5A O2 C8A C7A -9.8(19) . .
Eu1 O2 C8A C7A 150.1(6) . .
C6A C7A C8A O2 29.7(13) . .
N1 N2 C9 C10 -1.5(3) . .
Eu1 N2 C9 C10 71.7(2) . .
N1 N2 C9 C16 176.5(2) . .
Eu1 N2 C9 C16 -110.3(2) . .
N1 N2 C9 Eu1 -73.16(15) . .
N2 C9 C10 C11 2.0(3) . .
C16 C9 C10 C11 -175.8(3) . .
Eu1 C9 C10 C11 62.21(18) . .
N2 C9 C10 Eu1 -60.24(18) . .
C16 C9 C10 Eu1 122.0(3) . .
N2 N1 C11 C10 0.9(3) . .
Eu1 N1 C11 C10 -75.07(19) . .
N2 N1 C11 C12 -175.2(2) . .
Eu1 N1 C11 C12 108.8(2) . .
N2 N1 C11 Eu1 75.98(15) . .
C9 C10 C11 N1 -1.7(3) . .
Eu1 C10 C11 N1 62.10(16) . .
C9 C10 C11 C12 173.9(3) . .
Eu1 C10 C11 C12 -122.3(3) . .
C9 C10 C11 Eu1 -63.84(19) . .
N1 C11 C12 C15 -174.0(3) . .
C10 C11 C12 C15 10.8(4) . .
Eu1 C11 C12 C15 -97.3(2) . .
N1 C11 C12 C13 -53.0(3) . .
C10 C11 C12 C13 131.8(3) . .
Eu1 C11 C12 C13 23.8(3) . .
N1 C11 C12 C14 66.0(3) . .
C10 C11 C12 C14 -109.2(3) . .
Eu1 C11 C12 C14 142.8(2) . .
N3 N4 C17 C18 -0.1(3) . .
N3 N4 C17 C21 -178.4(2) . .
N4 C17 C18 C19 -0.1(3) . .
C21 C17 C18 C19 178.1(3) . .
N4 N3 C19 C18 -0.2(3) . .
N4 N3 C19 C20 179.7(3) . .
C17 C18 C19 N3 0.2(3) . .
C17 C18 C19 C20 -179.7(3) . .
N4 C17 C21 C22 0.2(4) . .
C18 C17 C21 C22 -177.8(3) . .
N4 C17 C21 C23 -120.6(3) . .
C18 C17 C21 C23 61.4(4) . .
N4 C17 C21 C24 122.3(3) . .
C18 C17 C21 C24 -55.7(4) . .
