#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:25:20 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179245 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/65/4316594.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_4316594
loop_
_publ_author_name
'Ana de Bettencourt-Dias'
'Patrick S. Barber'
'Subha Viswanathan'
'Daniel T. de Lill'
'Alexandra Rollett'
'George Ling'
'Sultan Altun'
_publ_contact_author_address
;Department of Chemistry
University of Nevada, Reno
Reno, NV 89557-0216
;
_publ_contact_author_email       abd@unr.edu
_publ_contact_author_fax         1(775)7846804
_publ_contact_author_name        'Ana de Bettencourt-Dias'
_publ_contact_author_phone       1(775)6828421
_publ_section_title
;
 Para-Derivatized Pybox Ligands As Sensitizers in Highly Luminescent
 Ln(III) Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              8848
_journal_page_last               8861
_journal_paper_doi               10.1021/ic101034y
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C77 H88 Cl10 Eu2 N24 O36'
_chemical_formula_weight         2584.13
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.3670(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.3699(10)
_cell_length_b                   13.4059(9)
_cell_length_c                   25.8766(18)
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.56
_cell_measurement_theta_min      2.18
_cell_volume                     4963.1(6)
_computing_cell_refinement       'Bruker SMART (Bruker, 2001)'
_computing_data_collection       'Bruker SMART (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2001)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX 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  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            65992
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    1.618
_exptl_absorpt_correction_T_max  0.9381
_exptl_absorpt_correction_T_min  0.3971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS (Bruker 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2604
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.04
_refine_diff_density_max         2.243
_refine_diff_density_min         -2.219
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     679
_refine_ls_number_reflns         14461
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0437P)²+7.1579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1067
_reflns_number_gt                11507
_reflns_number_total             14461
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic101034y_si_002_3.cif
_cod_data_source_block           pyboxome3eu_gl_062309
_cod_database_code               4316594
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.521131(11) 0.134702(12) 0.825400(6) 0.01460(5) Uani 1 1 d . . .
C1 C 0.2759(2) 0.0888(3) 0.77879(15) 0.0249(7) Uani 1 1 d . . .
H1A H 0.2863 0.0163 0.7749 0.030 Uiso 1 1 calc R . .
H1B H 0.2778 0.1214 0.7446 0.030 Uiso 1 1 calc R . .
C2 C 0.1829(3) 0.1087(3) 0.80086(16) 0.0302(9) Uani 1 1 d . . .
H2A H 0.1397 0.1454 0.7756 0.036 Uiso 1 1 calc R . .
H2B H 0.1529 0.0454 0.8100 0.036 Uiso 1 1 calc R . .
C3 C 0.3014(2) 0.1736(3) 0.85210(14) 0.0200(7) Uani 1 1 d . . .
C4 C 0.3493(2) 0.2241(2) 0.89709(13) 0.0189(7) Uani 1 1 d . . .
C5 C 0.3036(3) 0.2710(3) 0.93502(15) 0.0249(8) Uani 1 1 d . . .
H5 H 0.2373 0.2729 0.9331 0.030 Uiso 1 1 calc R . .
C6 C 0.3579(3) 0.3155(3) 0.97612(15) 0.0280(8) Uani 1 1 d . . .
C7 C 0.4544(3) 0.3126(3) 0.97741(14) 0.0241(7) Uani 1 1 d . . .
H7 H 0.4928 0.3430 1.0049 0.029 Uiso 1 1 calc R . .
C8 C 0.4932(2) 0.2639(3) 0.93734(13) 0.0197(7) Uani 1 1 d . . .
C9 C 0.5947(2) 0.2566(3) 0.93383(13) 0.0203(7) Uani 1 1 d . . .
C10 C 0.7461(3) 0.2850(3) 0.95640(16) 0.0305(9) Uani 1 1 d . . .
H10A H 0.7825 0.2470 0.9842 0.037 Uiso 1 1 calc R . .
H10B H 0.7790 0.3485 0.9507 0.037 Uiso 1 1 calc R . .
C11 C 0.7326(2) 0.2239(3) 0.90607(15) 0.0248(8) Uani 1 1 d . . .
H11A H 0.7571 0.2602 0.8769 0.030 Uiso 1 1 calc R . .
H11B H 0.7646 0.1585 0.9103 0.030 Uiso 1 1 calc R . .
C12 C 0.4050(3) -0.0221(3) 0.92016(16) 0.0274(8) Uani 1 1 d . . .
H12A H 0.3473 -0.0314 0.8966 0.033 Uiso 1 1 calc R . .
H12B H 0.3948 0.0323 0.9449 0.033 Uiso 1 1 calc R . .
C13 C 0.4321(3) -0.1185(3) 0.9489(2) 0.0419(12) Uani 1 1 d . . .
H13A H 0.4320 -0.1094 0.9869 0.050 Uiso 1 1 calc R . .
H13B H 0.3885 -0.1731 0.9376 0.050 Uiso 1 1 calc R . .
C14 C 0.5464(2) -0.0672(3) 0.90196(13) 0.0203(7) Uani 1 1 d . . .
C15 C 0.6370(2) -0.0703(2) 0.88013(13) 0.0167(6) Uani 1 1 d . . .
C16 C 0.7045(2) -0.1416(3) 0.89430(13) 0.0188(6) Uani 1 1 d . . .
H16 H 0.6938 -0.1926 0.9185 0.023 Uiso 1 1 calc R . .
C17 C 0.7888(2) -0.1357(3) 0.87159(13) 0.0189(6) Uani 1 1 d . . .
C18 C 0.7987(2) -0.0620(2) 0.83412(13) 0.0178(6) Uani 1 1 d . . .
H18 H 0.8537 -0.0585 0.8165 0.021 Uiso 1 1 calc R . .
C19 C 0.7276(2) 0.0048(3) 0.82341(13) 0.0175(6) Uani 1 1 d . . .
C20 C 0.7331(2) 0.0900(3) 0.78788(13) 0.0205(7) Uani 1 1 d . . .
C21 C 0.7985(3) 0.1944(3) 0.73469(18) 0.0340(10) Uani 1 1 d . . .
H21A H 0.8025 0.1841 0.6971 0.041 Uiso 1 1 calc R . .
H21B H 0.8472 0.2428 0.7478 0.041 Uiso 1 1 calc R . .
C22 C 0.7013(3) 0.2310(3) 0.74517(15) 0.0244(8) Uani 1 1 d . . .
H22A H 0.7044 0.2985 0.7608 0.029 Uiso 1 1 calc R . .
H22B H 0.6588 0.2327 0.7128 0.029 Uiso 1 1 calc R . .
C23 C 0.5346(3) 0.4143(3) 0.83810(15) 0.0331(9) Uani 1 1 d . . .
H23A H 0.6004 0.4144 0.8534 0.040 Uiso 1 1 calc R . .
H23B H 0.4930 0.4197 0.8664 0.040 Uiso 1 1 calc R . .
C24 C 0.5168(3) 0.4998(3) 0.79926(15) 0.0315(9) Uani 1 1 d . . .
H24A H 0.4672 0.5446 0.8097 0.038 Uiso 1 1 calc R . .
H24B H 0.5745 0.5391 0.7965 0.038 Uiso 1 1 calc R . .
C25 C 0.4887(3) 0.3522(2) 0.76070(14) 0.0208(7) Uani 1 1 d . . .
C26 C 0.4660(2) 0.2834(3) 0.71768(14) 0.0188(7) Uani 1 1 d . . .
C27 C 0.4442(2) 0.3152(3) 0.66752(14) 0.0209(7) Uani 1 1 d . . .
H27 H 0.4402 0.3842 0.6594 0.025 Uiso 1 1 calc R . .
C28 C 0.4279(3) 0.2429(3) 0.62898(14) 0.0233(7) Uani 1 1 d . . .
C29 C 0.4357(3) 0.1426(3) 0.64257(14) 0.0227(7) Uani 1 1 d . . .
H29 H 0.4258 0.0918 0.6171 0.027 Uiso 1 1 calc R . .
C30 C 0.4583(2) 0.1192(2) 0.69398(13) 0.0189(7) Uani 1 1 d . . .
C31 C 0.4684(2) 0.0159(3) 0.71259(13) 0.0200(7) Uani 1 1 d . . .
C32 C 0.4608(3) -0.1495(3) 0.70760(16) 0.0313(9) Uani 1 1 d . . .
H32A H 0.5061 -0.1965 0.6942 0.038 Uiso 1 1 calc R . .
H32B H 0.3989 -0.1822 0.7063 0.038 Uiso 1 1 calc R . .
C33 C 0.4937(3) -0.1160(3) 0.76290(15) 0.0256(8) Uani 1 1 d . . .
H33A H 0.4528 -0.1435 0.7882 0.031 Uiso 1 1 calc R . .
H33B H 0.5588 -0.1375 0.7728 0.031 Uiso 1 1 calc R . .
C34 C 0.3638(3) 0.4142(4) 1.05326(18) 0.0449(12) Uani 1 1 d . . .
H34A H 0.4072 0.3684 1.0727 0.067 Uiso 1 1 calc R . .
H34B H 0.3211 0.4427 1.0767 0.067 Uiso 1 1 calc R . .
H34C H 0.3991 0.4679 1.0384 0.067 Uiso 1 1 calc R . .
C35 C 0.8558(3) -0.2659(3) 0.92494(16) 0.0321(9) Uani 1 1 d . . .
H35A H 0.8370 -0.2309 0.9555 0.048 Uiso 1 1 calc R . .
H35B H 0.9169 -0.2974 0.9335 0.048 Uiso 1 1 calc R . .
H35C H 0.8094 -0.3172 0.9142 0.048 Uiso 1 1 calc R . .
C36 C 0.4052(4) 0.3657(3) 0.56296(16) 0.0378(10) Uani 1 1 d . . .
H36A H 0.3588 0.4017 0.5813 0.057 Uiso 1 1 calc R . .
H36B H 0.3884 0.3705 0.5255 0.057 Uiso 1 1 calc R . .
H36C H 0.4670 0.3953 0.5716 0.057 Uiso 1 1 calc R . .
C37 C 0.0187(3) 0.1262(3) 0.92769(16) 0.0371(10) Uani 1 1 d . . .
H37A H -0.0176 0.0864 0.9510 0.045 Uiso 1 1 calc R . .
H37B H 0.0852 0.1062 0.9339 0.045 Uiso 1 1 calc R . .
C38 C 0.7150(3) 0.4492(5) 0.1138(2) 0.0659(19) Uani 1 1 d . . .
H38A H 0.7643 0.4640 0.0906 0.079 Uiso 1 1 calc R . .
H38B H 0.7284 0.3828 0.1295 0.079 Uiso 1 1 calc R . .
Cl1 Cl -0.02202(8) 0.10163(9) 0.86274(4) 0.0370(2) Uani 1 1 d . . .
Cl2 Cl 0.00760(14) 0.25369(11) 0.94163(6) 0.0726(5) Uani 1 1 d . . .
Cl3 Cl 0.71882(11) 0.53876(12) 0.16289(6) 0.0693(5) Uani 1 1 d . . .
Cl4 Cl 0.60689(11) 0.44561(12) 0.07714(5) 0.0626(4) Uani 1 1 d . . .
N1 N 0.3462(2) 0.1322(2) 0.81736(11) 0.0191(5) Uani 1 1 d . . .
N2 N 0.4427(2) 0.2198(2) 0.89761(11) 0.0181(6) Uani 1 1 d . . .
N3 N 0.6300(2) 0.2109(2) 0.89711(11) 0.0202(6) Uani 1 1 d . . .
N4 N 0.4855(2) 0.0005(2) 0.89033(11) 0.0202(6) Uani 1 1 d . . .
N5 N 0.64704(19) 0.0025(2) 0.84595(11) 0.0173(5) Uani 1 1 d . . .
N6 N 0.6697(2) 0.1565(2) 0.78198(11) 0.0179(6) Uani 1 1 d . . .
N7 N 0.5136(2) 0.3229(2) 0.80686(12) 0.0204(6) Uani 1 1 d . . .
N8 N 0.4728(2) 0.1870(2) 0.73194(11) 0.0169(5) Uani 1 1 d . . .
N9 N 0.4869(2) -0.0060(2) 0.76070(11) 0.0185(6) Uani 1 1 d . . .
N10 N 0.6922(2) 0.9776(2) 0.66843(13) 0.0265(7) Uani 1 1 d . . .
N11 N 0.2214(3) 0.3061(4) 0.6937(2) 0.0556(13) Uani 1 1 d . . .
N12 N 0.7767(2) 0.9811(3) 0.98954(12) 0.0274(7) Uani 1 1 d . . .
O1 O 0.20807(17) 0.1694(2) 0.84744(11) 0.0262(6) Uani 1 1 d . . .
O2 O 0.65094(18) 0.3039(2) 0.96998(10) 0.0260(6) Uani 1 1 d . . .
O3 O 0.52705(18) -0.1402(2) 0.93486(11) 0.0299(6) Uani 1 1 d . . .
O4 O 0.80981(17) 0.0998(2) 0.76290(10) 0.0248(5) Uani 1 1 d . . .
O5 O 0.4876(2) 0.45008(19) 0.75033(10) 0.0289(6) Uani 1 1 d . . .
O6 O 0.4557(2) -0.05702(19) 0.67779(10) 0.0287(6) Uani 1 1 d . . .
O7 O 0.3107(2) 0.3606(3) 1.01211(13) 0.0448(9) Uani 1 1 d . . .
O8 O 0.86199(18) -0.19550(19) 0.88307(10) 0.0236(5) Uani 1 1 d . . .
O9 O 0.4069(2) 0.2629(2) 0.57830(10) 0.0307(6) Uani 1 1 d . . .
O10 O 0.6518(3) 1.0590(2) 0.66707(14) 0.0497(9) Uani 1 1 d . . .
O11 O 0.6806(3) 0.9189(3) 0.70413(14) 0.0534(9) Uani 1 1 d . . .
O12 O 0.7429(4) 0.9562(3) 0.63544(19) 0.0862(16) Uani 1 1 d . . .
O13 O 0.2415(3) 0.3601(5) 0.6573(2) 0.115(2) Uani 1 1 d . . .
O14 O 0.1677(4) 0.2326(4) 0.68436(19) 0.0853(16) Uani 1 1 d . . .
O15 O 0.2525(3) 0.3241(3) 0.73825(17) 0.0607(10) Uani 1 1 d . . .
O16 O 0.8501(2) 0.9898(3) 0.96793(12) 0.0422(8) Uani 1 1 d . . .
O17 O 0.7126(2) 1.0436(2) 0.98168(12) 0.0396(7) Uani 1 1 d . . .
O18 O 0.7672(2) 0.9094(2) 1.01864(13) 0.0433(8) Uani 1 1 d . . .
ClS Cl 0.0958(2) 0.48709(18) -0.01328(9) 0.1401(12) Uani 1 1 d D . .
C1S C 0.0432(8) 0.5123(10) 0.0411(5) 0.085(5) Uani 0.50 1 d PD . .
H1SA H 0.0629 0.5779 0.0559 0.101 Uiso 0.50 1 calc PR . .
H1SB H 0.0565 0.4599 0.0678 0.101 Uiso 0.50 1 calc PR . .
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'
Cl Cl 0.1484 0.1585 '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
N1 Eu1 N6 148.25(9) . . ?
N1 Eu1 N3 127.89(9) . . ?
N6 Eu1 N3 77.79(9) . . ?
N1 Eu1 N9 78.71(9) . . ?
N6 Eu1 N9 84.95(9) . . ?
N3 Eu1 N9 148.47(9) . . ?
N1 Eu1 N2 63.64(9) . . ?
N6 Eu1 N2 136.74(9) . . ?
N3 Eu1 N2 64.25(9) . . ?
N9 Eu1 N2 138.27(9) . . ?
N1 Eu1 N4 77.46(9) . . ?
N6 Eu1 N4 127.37(9) . . ?
N3 Eu1 N4 87.12(10) . . ?
N9 Eu1 N4 82.65(10) . . ?
N2 Eu1 N4 72.62(9) . . ?
N1 Eu1 N8 75.09(9) . . ?
N6 Eu1 N8 73.30(9) . . ?
N3 Eu1 N8 132.82(9) . . ?
N9 Eu1 N8 63.92(9) . . ?
N2 Eu1 N8 118.26(9) . . ?
N4 Eu1 N8 140.01(9) . . ?
N1 Eu1 N5 133.99(9) . . ?
N6 Eu1 N5 63.90(9) . . ?
N3 Eu1 N5 75.50(9) . . ?
N9 Eu1 N5 73.23(9) . . ?
N2 Eu1 N5 120.86(9) . . ?
N4 Eu1 N5 63.53(9) . . ?
N8 Eu1 N5 120.88(9) . . ?
N1 Eu1 N7 88.48(10) . . ?
N6 Eu1 N7 79.94(9) . . ?
N3 Eu1 N7 75.68(10) . . ?
N9 Eu1 N7 127.17(9) . . ?
N2 Eu1 N7 71.51(9) . . ?
N4 Eu1 N7 144.07(9) . . ?
N8 Eu1 N7 63.25(9) . . ?
N5 Eu1 N7 137.51(9) . . ?
N1 C1 C2 104.3(3) . . ?
N1 C1 H1A 110.9 . . ?
C2 C1 H1A 110.9 . . ?
N1 C1 H1B 110.9 . . ?
C2 C1 H1B 110.9 . . ?
H1A C1 H1B 108.9 . . ?
O1 C2 C1 104.3(3) . . ?
O1 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
O1 C2 H2B 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
N1 C3 O1 119.0(3) . . ?
N1 C3 C4 122.0(3) . . ?
O1 C3 C4 119.0(3) . . ?
N2 C4 C5 123.6(3) . . ?
N2 C4 C3 112.6(3) . . ?
C5 C4 C3 123.8(3) . . ?
C4 C5 C6 117.9(3) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
O7 C6 C7 124.4(4) . . ?
O7 C6 C5 116.0(4) . . ?
C7 C6 C5 119.6(3) . . ?
C6 C7 C8 117.9(3) . . ?
C6 C7 H7 121.1 . . ?
C8 C7 H7 121.1 . . ?
N2 C8 C7 123.7(3) . . ?
N2 C8 C9 113.1(3) . . ?
C7 C8 C9 123.2(3) . . ?
N3 C9 O2 119.5(3) . . ?
N3 C9 C8 122.9(3) . . ?
O2 C9 C8 117.5(3) . . ?
O2 C10 C11 104.4(3) . . ?
O2 C10 H10A 110.9 . . ?
C11 C10 H10A 110.9 . . ?
O2 C10 H10B 110.9 . . ?
C11 C10 H10B 110.9 . . ?
H10A C10 H10B 108.9 . . ?
N3 C11 C10 103.9(3) . . ?
N3 C11 H11A 111.0 . . ?
C10 C11 H11A 111.0 . . ?
N3 C11 H11B 111.0 . . ?
C10 C11 H11B 111.0 . . ?
H11A C11 H11B 109.0 . . ?
N4 C12 C13 104.6(3) . . ?
N4 C12 H12A 110.8 . . ?
C13 C12 H12A 110.8 . . ?
N4 C12 H12B 110.8 . . ?
C13 C12 H12B 110.8 . . ?
H12A C12 H12B 108.9 . . ?
O3 C13 C12 104.3(3) . . ?
O3 C13 H13A 110.9 . . ?
C12 C13 H13A 110.9 . . ?
O3 C13 H13B 110.9 . . ?
C12 C13 H13B 110.9 . . ?
H13A C13 H13B 108.9 . . ?
N4 C14 O3 119.3(3) . . ?
N4 C14 C15 122.9(3) . . ?
O3 C14 C15 117.8(3) . . ?
N5 C15 C16 124.3(3) . . ?
N5 C15 C14 112.9(3) . . ?
C16 C15 C14 122.8(3) . . ?
C15 C16 C17 117.5(3) . . ?
C15 C16 H16 121.2 . . ?
C17 C16 H16 121.2 . . ?
O8 C17 C16 124.7(3) . . ?
O8 C17 C18 116.7(3) . . ?
C16 C17 C18 118.6(3) . . ?
C19 C18 C17 118.7(3) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
N5 C19 C18 123.7(3) . . ?
N5 C19 C20 112.8(3) . . ?
C18 C19 C20 123.5(3) . . ?
N6 C20 O4 119.1(3) . . ?
N6 C20 C19 122.6(3) . . ?
O4 C20 C19 118.3(3) . . ?
O4 C21 C22 104.5(3) . . ?
O4 C21 H21A 110.9 . . ?
C22 C21 H21A 110.9 . . ?
O4 C21 H21B 110.9 . . ?
C22 C21 H21B 110.9 . . ?
H21A C21 H21B 108.9 . . ?
N6 C22 C21 103.8(3) . . ?
N6 C22 H22A 111.0 . . ?
C21 C22 H22A 111.0 . . ?
N6 C22 H22B 111.0 . . ?
C21 C22 H22B 111.0 . . ?
H22A C22 H22B 109.0 . . ?
N7 C23 C24 104.3(3) . . ?
N7 C23 H23A 110.9 . . ?
C24 C23 H23A 110.9 . . ?
N7 C23 H23B 110.9 . . ?
C24 C23 H23B 110.9 . . ?
H23A C23 H23B 108.9 . . ?
O5 C24 C23 104.2(3) . . ?
O5 C24 H24A 110.9 . . ?
C23 C24 H24A 110.9 . . ?
O5 C24 H24B 110.9 . . ?
C23 C24 H24B 110.9 . . ?
H24A C24 H24B 108.9 . . ?
N7 C25 O5 119.1(3) . . ?
N7 C25 C26 122.8(3) . . ?
O5 C25 C26 118.0(3) . . ?
N8 C26 C27 124.2(3) . . ?
N8 C26 C25 113.1(3) . . ?
C27 C26 C25 122.6(3) . . ?
C26 C27 C28 117.9(3) . . ?
C26 C27 H27 121.1 . . ?
C28 C27 H27 121.1 . . ?
O9 C28 C29 116.4(3) . . ?
O9 C28 C27 124.4(3) . . ?
C29 C28 C27 119.1(3) . . ?
C30 C29 C28 118.1(3) . . ?
C30 C29 H29 120.9 . . ?
C28 C29 H29 120.9 . . ?
N8 C30 C29 124.1(3) . . ?
N8 C30 C31 113.3(3) . . ?
C29 C30 C31 122.7(3) . . ?
N9 C31 O6 119.5(3) . . ?
N9 C31 C30 122.6(3) . . ?
O6 C31 C30 117.9(3) . . ?
O6 C32 C33 103.9(3) . . ?
O6 C32 H32A 111.0 . . ?
C33 C32 H32A 111.0 . . ?
O6 C32 H32B 111.0 . . ?
C33 C32 H32B 111.0 . . ?
H32A C32 H32B 109.0 . . ?
N9 C33 C32 104.1(3) . . ?
N9 C33 H33A 110.9 . . ?
C32 C33 H33A 110.9 . . ?
N9 C33 H33B 110.9 . . ?
C32 C33 H33B 110.9 . . ?
H33A C33 H33B 109.0 . . ?
O7 C34 H34A 109.5 . . ?
O7 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O7 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O8 C35 H35A 109.5 . . ?
O8 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O8 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O9 C36 H36A 109.5 . . ?
O9 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O9 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
Cl2 C37 Cl1 110.5(2) . . ?
Cl2 C37 H37A 109.6 . . ?
Cl1 C37 H37A 109.6 . . ?
Cl2 C37 H37B 109.6 . . ?
Cl1 C37 H37B 109.6 . . ?
H37A C37 H37B 108.1 . . ?
Cl4 C38 Cl3 112.4(3) . . ?
Cl4 C38 H38A 109.1 . . ?
Cl3 C38 H38A 109.1 . . ?
Cl4 C38 H38B 109.1 . . ?
Cl3 C38 H38B 109.1 . . ?
H38A C38 H38B 107.9 . . ?
C3 N1 C1 106.8(3) . . ?
C3 N1 Eu1 120.2(2) . . ?
C1 N1 Eu1 133.0(2) . . ?
C8 N2 C4 117.3(3) . . ?
C8 N2 Eu1 121.1(2) . . ?
C4 N2 Eu1 121.6(2) . . ?
C9 N3 C11 106.6(3) . . ?
C9 N3 Eu1 118.6(2) . . ?
C11 N3 Eu1 134.5(2) . . ?
C14 N4 C12 106.4(3) . . ?
C14 N4 Eu1 118.8(2) . . ?
C12 N4 Eu1 134.7(2) . . ?
C15 N5 C19 117.0(3) . . ?
C15 N5 Eu1 121.9(2) . . ?
C19 N5 Eu1 121.1(2) . . ?
C20 N6 C22 106.9(3) . . ?
C20 N6 Eu1 119.4(2) . . ?
C22 N6 Eu1 133.5(2) . . ?
C25 N7 C23 106.3(3) . . ?
C25 N7 Eu1 118.7(2) . . ?
C23 N7 Eu1 135.0(2) . . ?
C30 N8 C26 116.6(3) . . ?
C30 N8 Eu1 121.2(2) . . ?
C26 N8 Eu1 122.1(2) . . ?
C31 N9 C33 105.8(3) . . ?
C31 N9 Eu1 118.7(2) . . ?
C33 N9 Eu1 135.0(2) . . ?
O12 N10 O10 120.2(4) . . ?
O12 N10 O11 120.6(4) . . ?
O10 N10 O11 119.2(4) . . ?
O15 N11 O13 120.7(6) . . ?
O15 N11 O14 119.9(5) . . ?
O13 N11 O14 119.4(6) . . ?
O18 N12 O16 119.5(4) . . ?
O18 N12 O17 120.0(3) . . ?
O16 N12 O17 120.5(4) . . ?
C3 O1 C2 105.4(3) . . ?
C9 O2 C10 105.5(3) . . ?
C14 O3 C13 105.3(3) . . ?
C20 O4 C21 105.6(3) . . ?
C25 O5 C24 106.0(3) . . ?
C31 O6 C32 105.7(3) . . ?
C6 O7 C34 118.0(3) . . ?
C17 O8 C35 117.2(3) . . ?
C28 O9 C36 117.3(3) . . ?
C1S ClS C1S 78.2(7) . 3_565 ?
ClS C1S ClS 101.8(7) . 3_565 ?
ClS C1S H1SA 111.4 . . ?
ClS C1S H1SA 111.4 3_565 . ?
ClS C1S H1SB 111.4 . . ?
ClS C1S H1SB 111.4 3_565 . ?
H1SA C1S H1SB 109.3 . . ?
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 N1 2.504(3) . ?
Eu1 N6 2.521(3) . ?
Eu1 N3 2.528(3) . ?
Eu1 N9 2.539(3) . ?
Eu1 N2 2.541(3) . ?
Eu1 N4 2.546(3) . ?
Eu1 N8 2.551(3) . ?
Eu1 N5 2.553(3) . ?
Eu1 N7 2.569(3) . ?
C1 N1 1.472(4) . ?
C1 C2 1.525(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 O1 1.472(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N1 1.280(4) . ?
C3 O1 1.336(4) . ?
C3 C4 1.463(5) . ?
C4 N2 1.341(4) . ?
C4 C5 1.382(5) . ?
C5 C6 1.393(5) . ?
C5 H5 0.9500 . ?
C6 O7 1.345(4) . ?
C6 C7 1.385(5) . ?
C7 C8 1.386(5) . ?
C7 H7 0.9500 . ?
C8 N2 1.340(4) . ?
C8 C9 1.473(5) . ?
C9 N3 1.275(4) . ?
C9 O2 1.337(4) . ?
C10 O2 1.466(5) . ?
C10 C11 1.536(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N3 1.482(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N4 1.481(4) . ?
C12 C13 1.523(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O3 1.473(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N4 1.276(4) . ?
C14 O3 1.343(4) . ?
C14 C15 1.468(5) . ?
C15 N5 1.334(4) . ?
C15 C16 1.386(5) . ?
C16 C17 1.397(5) . ?
C16 H16 0.9500 . ?
C17 O8 1.334(4) . ?
C17 C18 1.401(5) . ?
C18 C19 1.367(5) . ?
C18 H18 0.9500 . ?
C19 N5 1.345(4) . ?
C19 C20 1.473(5) . ?
C20 N6 1.274(5) . ?
C20 O4 1.335(4) . ?
C21 O4 1.465(5) . ?
C21 C22 1.529(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 N6 1.480(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 N7 1.484(5) . ?
C23 C24 1.529(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 O5 1.457(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 N7 1.276(5) . ?
C25 O5 1.339(4) . ?
C25 C26 1.459(5) . ?
C26 N8 1.344(4) . ?
C26 C27 1.374(5) . ?
C27 C28 1.395(5) . ?
C27 H27 0.9500 . ?
C28 O9 1.345(4) . ?
C28 C29 1.391(5) . ?
C29 C30 1.376(5) . ?
C29 H29 0.9500 . ?
C30 N8 1.341(4) . ?
C30 C31 1.469(5) . ?
C31 N9 1.282(4) . ?
C31 O6 1.330(4) . ?
C32 O6 1.459(5) . ?
C32 C33 1.532(6) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 N9 1.479(4) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 O7 1.442(5) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 O8 1.446(4) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 O9 1.434(5) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 Cl2 1.757(5) . ?
C37 Cl1 1.759(4) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 Cl4 1.743(5) . ?
C38 Cl3 1.746(7) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
N10 O12 1.207(5) . ?
N10 O10 1.235(4) . ?
N10 O11 1.237(4) . ?
N11 O15 1.221(6) . ?
N11 O13 1.244(6) . ?
N11 O14 1.261(7) . ?
N12 O18 1.237(4) . ?
N12 O16 1.245(4) . ?
N12 O17 1.247(4) . ?
ClS C1S 1.693(13) . ?
ClS C1S 2.059(11) 3_565 ?
C1S ClS 2.059(11) 3_565 ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
