#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/53/2215341.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2215341
loop_
_publ_author_name
'Liu, Yu-Fen'
'Xia, Hai-Tao'
'Wang, Da-Qi'
'Yang, Shu-Ping'
_publ_section_title
;
 Hexakis(μ-naphthalene-1-acetato)bis[(1,10-phenanthroline)europium(III)]
 N,N-dimethylformamide disolvate
;
_journal_coeditor_code           AT2403
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2608
_journal_page_last               m2609
_journal_paper_doi               10.1107/S1600536807046818
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac
'[Eu2 (C12 H9 O2)6 (C12 H8 N2)2] , 2C3 H7 N O'
_chemical_formula_moiety         'C96 H70 Eu2 N4 O12 , 2C3 H7 N O'
_chemical_formula_sum            'C102 H84 Eu2 N6 O14'
_chemical_formula_weight         1921.67
_chemical_name_systematic
;
Hexakis(μ-naphthalene-1-acetato)bis[(1,10-phenanthroline)europium(III)]
N,N-dimethylformamide disolvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.866(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.529(2)
_cell_length_b                   15.095(2)
_cell_length_c                   22.171(3)
_cell_measurement_reflns_used    3934
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.261
_cell_measurement_theta_min      2.413
_cell_volume                     4395.8(11)
_computing_cell_refinement       'SMART (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997b)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Siemens SMART 1000 CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0766
_diffrn_reflns_av_sigmaI/netI    0.1063
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21103
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.65
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.483
_exptl_absorpt_correction_T_max  0.8539
_exptl_absorpt_correction_T_min  0.5815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.674
_refine_diff_density_min         -1.389
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         7667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1197
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+24.9916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.1169
_reflns_number_gt                4416
_reflns_number_total             7667
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2403.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2215341
_cod_database_fobs_code          2215341
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Eu Eu1 0.38256(3) 0.42912(3) 1.011917(19) 0.03380(13) Uani d . 1
N N1 0.2282(5) 0.4434(4) 1.0646(3) 0.0408(17) Uani d . 1
N N2 0.2103(5) 0.3629(5) 0.9541(3) 0.0473(19) Uani d . 1
N N3 0.3673(9) 0.3365(7) 0.2527(5) 0.080(3) Uani d . 1
O O1 0.4398(4) 0.5807(3) 0.9788(2) 0.0348(12) Uani d . 1
O O2 0.2758(4) 0.5565(4) 0.9613(2) 0.0429(14) Uani d . 1
O O3 0.4044(4) 0.4244(4) 0.9082(2) 0.0396(13) Uani d . 1
O O4 0.5474(4) 0.4867(4) 0.8956(2) 0.0407(14) Uani d . 1
O O5 0.4121(5) 0.2712(4) 0.9892(3) 0.0511(16) Uani d . 1
O O6 0.4044(4) 0.3010(4) 1.0838(3) 0.0527(16) Uani d . 1
O O7 0.2329(9) 0.2455(8) 0.2360(5) 0.152(4) Uani d . 1
C C1 0.3479(6) 0.5990(5) 0.9511(4) 0.035(2) Uani d . 1
C C2 0.3339(6) 0.6740(6) 0.9052(4) 0.051(2) Uani d . 1
H H2A 0.3589 0.7280 0.9274 0.061 Uiso calc R 1
H H2B 0.3757 0.6626 0.8761 0.061 Uiso calc R 1
C C3 0.2264(7) 0.6893(7) 0.8691(4) 0.051(3) Uani d . 1
C C4 0.1781(8) 0.7624(7) 0.8795(5) 0.064(3) Uani d . 1
H H4 0.2122 0.8021 0.9094 0.077 Uiso calc R 1
C C5 0.0777(8) 0.7824(8) 0.8474(5) 0.072(3) Uani d . 1
H H5 0.0462 0.8343 0.8556 0.087 Uiso calc R 1
C C6 0.0290(8) 0.7249(8) 0.8048(5) 0.067(3) Uani d . 1
H H6 -0.0382 0.7368 0.7844 0.081 Uiso calc R 1
C C7 0.0740(8) 0.6484(7) 0.7896(5) 0.062(3) Uani d . 1
C C8 0.1765(7) 0.6296(7) 0.8229(4) 0.056(3) Uani d . 1
C C9 0.2210(8) 0.5517(7) 0.8089(5) 0.071(3) Uani d . 1
H H9 0.2868 0.5382 0.8310 0.085 Uiso calc R 1
C C10 0.1725(10) 0.4944(8) 0.7645(5) 0.093(4) Uani d . 1
H H10 0.2047 0.4434 0.7554 0.111 Uiso calc R 1
C C11 0.0718(10) 0.5146(9) 0.7324(6) 0.095(4) Uani d . 1
H H11 0.0367 0.4754 0.7025 0.114 Uiso calc R 1
C C12 0.0257(9) 0.5885(8) 0.7441(5) 0.084(4) Uani d . 1
H H12 -0.0402 0.6004 0.7214 0.100 Uiso calc R 1
C C13 0.4723(6) 0.4354(6) 0.8798(3) 0.0374(19) Uani d . 1
C C14 0.4617(7) 0.3844(6) 0.8197(4) 0.054(3) Uani d . 1
H H14A 0.4137 0.3365 0.8192 0.065 Uiso calc R 1
H H14B 0.4322 0.4238 0.7855 0.065 Uiso calc R 1
C C15 0.5582(7) 0.3455(7) 0.8076(5) 0.058(3) Uani d . 1
C C16 0.5895(8) 0.3710(7) 0.7563(5) 0.070(3) Uani d . 1
H H16 0.5524 0.4138 0.7302 0.084 Uiso calc R 1
C C17 0.6765(9) 0.3345(8) 0.7415(5) 0.077(3) Uani d . 1
H H17 0.6971 0.3534 0.7065 0.093 Uiso calc R 1
C C18 0.7293(9) 0.2717(8) 0.7789(6) 0.078(3) Uani d . 1
H H18 0.7878 0.2489 0.7696 0.094 Uiso calc R 1
C C19 0.7005(8) 0.2395(8) 0.8306(6) 0.069(3) Uani d . 1
C C20 0.6133(8) 0.2796(7) 0.8466(5) 0.059(3) Uani d . 1
C C21 0.5844(8) 0.2474(7) 0.8991(5) 0.067(3) Uani d . 1
H H21 0.5290 0.2725 0.9108 0.080 Uiso calc R 1
C C22 0.6365(9) 0.1793(8) 0.9334(6) 0.085(4) Uani d . 1
H H22 0.6154 0.1581 0.9677 0.102 Uiso calc R 1
C C23 0.7216(10) 0.1409(8) 0.9176(6) 0.091(4) Uani d . 1
H H23 0.7569 0.0947 0.9410 0.109 Uiso calc R 1
C C24 0.7510(9) 0.1721(8) 0.8679(6) 0.082(4) Uani d . 1
H H24 0.8080 0.1472 0.8580 0.098 Uiso calc R 1
C C25 0.4104(7) 0.2472(6) 1.0421(5) 0.049(2) Uani d . 1
C C26 0.4134(8) 0.1476(6) 1.0558(5) 0.067(3) Uani d . 1
H H26A 0.4796 0.1242 1.0544 0.081 Uiso calc R 1
H H26B 0.4041 0.1380 1.0974 0.081 Uiso calc R 1
C C27 0.3332(10) 0.0995(7) 1.0104(6) 0.075(3) Uani d . 1
C C28 0.3575(10) 0.0461(7) 0.9655(6) 0.087(4) Uani d . 1
H H28 0.4250 0.0382 0.9639 0.105 Uiso calc R 1
C C29 0.2783(14) 0.0038(8) 0.9222(7) 0.102(4) Uani d . 1
H H29 0.2948 -0.0338 0.8928 0.122 Uiso calc R 1
C C30 0.1817(14) 0.0155(9) 0.9219(7) 0.106(5) Uani d . 1
H H30 0.1322 -0.0127 0.8916 0.128 Uiso calc R 1
C C31 0.1516(12) 0.0680(9) 0.9648(7) 0.093(4) Uani d . 1
C C32 0.2295(10) 0.1096(7) 1.0102(6) 0.078(3) Uani d . 1
C C33 0.1995(10) 0.1613(7) 1.0562(6) 0.081(4) Uani d . 1
H H33 0.2489 0.1879 1.0875 0.097 Uiso calc R 1
C C34 0.0969(11) 0.1725(8) 1.0550(6) 0.091(4) Uani d . 1
H H34 0.0769 0.2064 1.0851 0.109 Uiso calc R 1
C C35 0.0267(11) 0.1329(9) 1.0089(8) 0.103(5) Uani d . 1
H H35 -0.0418 0.1421 1.0076 0.124 Uiso calc R 1
C C36 0.0488(12) 0.0830(10) 0.9664(7) 0.105(5) Uani d . 1
H H36 -0.0033 0.0567 0.9367 0.126 Uiso calc R 1
C C37 0.2361(7) 0.4825(6) 1.1183(5) 0.053(3) Uani d . 1
H H37 0.2995 0.5043 1.1388 0.064 Uiso calc R 1
C C38 0.1536(8) 0.4935(7) 1.1472(5) 0.064(3) Uani d . 1
H H38 0.1627 0.5216 1.1855 0.076 Uiso calc R 1
C C39 0.0615(7) 0.4618(6) 1.1171(5) 0.060(3) Uani d . 1
H H39 0.0060 0.4678 1.1347 0.072 Uiso calc R 1
C C40 0.0497(6) 0.4202(7) 1.0598(5) 0.054(2) Uani d . 1
C C41 0.1347(6) 0.4122(6) 1.0349(4) 0.048(2) Uani d . 1
C C42 0.1262(7) 0.3708(6) 0.9760(5) 0.053(3) Uani d . 1
C C43 0.0299(8) 0.3387(7) 0.9433(5) 0.066(3) Uani d . 1
C C44 0.0262(8) 0.2989(7) 0.8856(6) 0.079(4) Uani d . 1
H H44 -0.0354 0.2774 0.8620 0.095 Uiso calc R 1
C C45 0.1105(8) 0.2915(8) 0.8642(5) 0.080(3) Uani d . 1
H H45 0.1079 0.2647 0.8261 0.097 Uiso calc R 1
C C46 0.2017(7) 0.3245(7) 0.8998(5) 0.065(3) Uani d . 1
H H46 0.2597 0.3192 0.8845 0.078 Uiso calc R 1
C C47 -0.0453(7) 0.3864(7) 1.0257(6) 0.068(3) Uani d . 1
H H47 -0.1023 0.3911 1.0420 0.081 Uiso calc R 1
C C48 -0.0538(7) 0.3482(7) 0.9709(6) 0.070(3) Uani d . 1
H H48 -0.1171 0.3268 0.9497 0.084 Uiso calc R 1
C C49 0.3093(12) 0.2756(11) 0.2205(7) 0.111(5) Uani d . 1
H H49 0.3254 0.2539 0.1848 0.133 Uiso calc R 1
C C50 0.4563(9) 0.3670(8) 0.2346(6) 0.098(4) Uani d . 1
H H50A 0.4694 0.3292 0.2026 0.146 Uiso calc R 1
H H50B 0.5135 0.3657 0.2698 0.146 Uiso calc R 1
H H50C 0.4454 0.4265 0.2192 0.146 Uiso calc R 1
C C51 0.3418(11) 0.3734(10) 0.3059(6) 0.137(6) Uani d . 1
H H51A 0.2725 0.3590 0.3055 0.206 Uiso calc R 1
H H51B 0.3496 0.4366 0.3055 0.206 Uiso calc R 1
H H51C 0.3861 0.3495 0.3428 0.206 Uiso calc R 1
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O1 Eu1 O3 3_667 . 73.98(16)
O1 Eu1 O4 3_667 3_667 77.01(17)
O3 Eu1 O4 . 3_667 136.22(18)
O1 Eu1 O6 3_667 . 86.18(19)
O3 Eu1 O6 . . 124.9(2)
O4 Eu1 O6 3_667 . 84.4(2)
O1 Eu1 O5 3_667 . 75.43(18)
O3 Eu1 O5 . . 73.3(2)
O4 Eu1 O5 3_667 . 129.0(2)
O6 Eu1 O5 . . 51.9(2)
O1 Eu1 O2 3_667 . 123.48(18)
O3 Eu1 O2 . . 77.43(18)
O4 Eu1 O2 3_667 . 92.48(18)
O6 Eu1 O2 . . 148.75(19)
O5 Eu1 O2 . . 138.44(19)
O1 Eu1 O1 3_667 . 73.28(19)
O3 Eu1 O1 . . 68.75(18)
O4 Eu1 O1 3_667 . 71.92(17)
O6 Eu1 O1 . . 151.40(18)
O5 Eu1 O1 . . 135.95(19)
O2 Eu1 O1 . . 51.02(16)
O1 Eu1 N2 3_667 . 142.8(2)
O3 Eu1 N2 . . 79.4(2)
O4 Eu1 N2 3_667 . 138.9(2)
O6 Eu1 N2 . . 88.4(2)
O5 Eu1 N2 . . 72.4(2)
O2 Eu1 N2 . . 73.7(2)
O1 Eu1 N2 . . 120.01(19)
O1 Eu1 N1 3_667 . 149.65(19)
O3 Eu1 N1 . . 136.33(19)
O4 Eu1 N1 3_667 . 76.7(2)
O6 Eu1 N1 . . 76.3(2)
O5 Eu1 N1 . . 110.6(2)
O2 Eu1 N1 . . 72.69(18)
O1 Eu1 N1 . . 112.18(18)
N2 Eu1 N1 . . 62.2(2)
O1 Eu1 Eu1 3_667 3_667 38.45(13)
O3 Eu1 Eu1 . 3_667 66.43(12)
O4 Eu1 Eu1 3_667 3_667 70.40(13)
O6 Eu1 Eu1 . 3_667 122.03(14)
O5 Eu1 Eu1 . 3_667 108.46(14)
O2 Eu1 Eu1 . 3_667 85.44(12)
O1 Eu1 Eu1 . 3_667 34.83(11)
N2 Eu1 Eu1 . 3_667 143.13(17)
N1 Eu1 Eu1 . 3_667 139.44(15)
C37 N1 C41 . . 117.4(7)
C37 N1 Eu1 . . 122.6(5)
C41 N1 Eu1 . . 120.0(6)
C46 N2 C42 . . 118.3(8)
C46 N2 Eu1 . . 119.8(6)
C42 N2 Eu1 . . 121.8(6)
C49 N3 C51 . . 119.8(14)
C49 N3 C50 . . 120.5(13)
C51 N3 C50 . . 119.7(12)
C1 O1 Eu1 . 3_667 154.9(5)
C1 O1 Eu1 . . 90.3(5)
Eu1 O1 Eu1 3_667 . 106.72(19)
C1 O2 Eu1 . . 94.9(5)
C13 O3 Eu1 . . 139.5(5)
C13 O4 Eu1 . 3_667 133.5(5)
C25 O5 Eu1 . . 92.8(5)
C25 O6 Eu1 . . 92.9(6)
O2 C1 O1 . . 121.3(7)
O2 C1 C2 . . 122.6(7)
O1 C1 C2 . . 116.0(7)
C3 C2 C1 . . 115.2(7)
C3 C2 H2A . . 108.5
C1 C2 H2A . . 108.5
C3 C2 H2B . . 108.5
C1 C2 H2B . . 108.5
H2A C2 H2B . . 107.5
C4 C3 C8 . . 119.1(9)
C4 C3 C2 . . 119.2(9)
C8 C3 C2 . . 121.6(9)
C3 C4 C5 . . 123.0(10)
C3 C4 H4 . . 118.5
C5 C4 H4 . . 118.5
C6 C5 C4 . . 118.2(11)
C6 C5 H5 . . 120.9
C4 C5 H5 . . 120.9
C5 C6 C7 . . 122.9(10)
C5 C6 H6 . . 118.6
C7 C6 H6 . . 118.6
C6 C7 C12 . . 124.0(11)
C6 C7 C8 . . 117.9(10)
C12 C7 C8 . . 118.1(11)
C9 C8 C3 . . 123.0(9)
C9 C8 C7 . . 118.1(10)
C3 C8 C7 . . 118.9(10)
C10 C9 C8 . . 122.7(11)
C10 C9 H9 . . 118.6
C8 C9 H9 . . 118.6
C9 C10 C11 . . 118.0(12)
C9 C10 H10 . . 121.0
C11 C10 H10 . . 121.0
C12 C11 C10 . . 121.5(12)
C12 C11 H11 . . 119.2
C10 C11 H11 . . 119.2
C11 C12 C7 . . 121.5(12)
C11 C12 H12 . . 119.2
C7 C12 H12 . . 119.2
O3 C13 O4 . . 126.0(8)
O3 C13 C14 . . 116.9(7)
O4 C13 C14 . . 117.1(7)
C15 C14 C13 . . 116.7(7)
C15 C14 H14A . . 108.1
C13 C14 H14A . . 108.1
C15 C14 H14B . . 108.1
C13 C14 H14B . . 108.1
H14A C14 H14B . . 107.3
C16 C15 C20 . . 119.2(10)
C16 C15 C14 . . 119.5(10)
C20 C15 C14 . . 121.2(9)
C15 C16 C17 . . 122.0(11)
C15 C16 H16 . . 119.0
C17 C16 H16 . . 119.0
C18 C17 C16 . . 118.7(11)
C18 C17 H17 . . 120.6
C16 C17 H17 . . 120.6
C17 C18 C19 . . 123.0(12)
C17 C18 H18 . . 118.5
C19 C18 H18 . . 118.5
C18 C19 C24 . . 123.8(12)
C18 C19 C20 . . 117.7(11)
C24 C19 C20 . . 118.4(12)
C21 C20 C15 . . 122.9(10)
C21 C20 C19 . . 117.8(11)
C15 C20 C19 . . 119.2(10)
C22 C21 C20 . . 120.8(11)
C22 C21 H21 . . 119.6
C20 C21 H21 . . 119.6
C21 C22 C23 . . 120.9(13)
C21 C22 H22 . . 119.6
C23 C22 H22 . . 119.6
C24 C23 C22 . . 118.8(13)
C24 C23 H23 . . 120.6
C22 C23 H23 . . 120.6
C23 C24 C19 . . 123.2(13)
C23 C24 H24 . . 118.4
C19 C24 H24 . . 118.4
O5 C25 O6 . . 122.2(9)
O5 C25 C26 . . 118.1(9)
O6 C25 C26 . . 119.7(10)
C27 C26 C25 . . 111.4(8)
C27 C26 H26A . . 109.3
C25 C26 H26A . . 109.3
C27 C26 H26B . . 109.3
C25 C26 H26B . . 109.3
H26A C26 H26B . . 108.0
C28 C27 C32 . . 118.0(12)
C28 C27 C26 . . 120.9(13)
C32 C27 C26 . . 121.1(12)
C27 C28 C29 . . 118.8(13)
C27 C28 H28 . . 120.6
C29 C28 H28 . . 120.6
C30 C29 C28 . . 122.3(15)
C30 C29 H29 . . 118.9
C28 C29 H29 . . 118.9
C29 C30 C31 . . 122.2(16)
C29 C30 H30 . . 118.9
C31 C30 H30 . . 118.9
C30 C31 C32 . . 117.0(15)
C30 C31 C36 . . 124.5(16)
C32 C31 C36 . . 118.5(16)
C27 C32 C31 . . 121.7(14)
C27 C32 C33 . . 120.8(12)
C31 C32 C33 . . 117.5(14)
C34 C33 C32 . . 120.6(12)
C34 C33 H33 . . 119.7
C32 C33 H33 . . 119.7
C35 C34 C33 . . 118.3(14)
C35 C34 H34 . . 120.8
C33 C34 H34 . . 120.8
C36 C35 C34 . . 124.2(17)
C36 C35 H35 . . 117.9
C34 C35 H35 . . 117.9
C35 C36 C31 . . 120.7(16)
C35 C36 H36 . . 119.6
C31 C36 H36 . . 119.6
N1 C37 C38 . . 124.1(9)
N1 C37 H37 . . 118.0
C38 C37 H37 . . 118.0
C39 C38 C37 . . 117.7(10)
C39 C38 H38 . . 121.2
C37 C38 H38 . . 121.2
C38 C39 C40 . . 120.1(9)
C38 C39 H39 . . 120.0
C40 C39 H39 . . 120.0
C39 C40 C41 . . 118.4(9)
C39 C40 C47 . . 122.6(9)
C41 C40 C47 . . 119.0(10)
N1 C41 C40 . . 122.4(9)
N1 C41 C42 . . 117.1(8)
C40 C41 C42 . . 120.4(9)
N2 C42 C43 . . 122.5(10)
N2 C42 C41 . . 118.7(8)
C43 C42 C41 . . 118.7(9)
C44 C43 C48 . . 125.4(10)
C44 C43 C42 . . 116.1(10)
C48 C43 C42 . . 118.5(11)
C45 C44 C43 . . 120.7(10)
C45 C44 H44 . . 119.6
C43 C44 H44 . . 119.6
C44 C45 C46 . . 119.0(11)
C44 C45 H45 . . 120.5
C46 C45 H45 . . 120.5
N2 C46 C45 . . 123.3(10)
N2 C46 H46 . . 118.3
C45 C46 H46 . . 118.3
C48 C47 C40 . . 120.9(10)
C48 C47 H47 . . 119.6
C40 C47 H47 . . 119.6
C47 C48 C43 . . 122.5(10)
C47 C48 H48 . . 118.7
C43 C48 H48 . . 118.7
O7 C49 N3 . . 122.3(17)
O7 C49 H49 . . 118.8
N3 C49 H49 . . 118.8
N3 C50 H50A . . 109.5
N3 C50 H50B . . 109.5
H50A C50 H50B . . 109.5
N3 C50 H50C . . 109.5
H50A C50 H50C . . 109.5
H50B C50 H50C . . 109.5
N3 C51 H51A . . 109.5
N3 C51 H51B . . 109.5
H51A C51 H51B . . 109.5
N3 C51 H51C . . 109.5
H51A C51 H51C . . 109.5
H51B C51 H51C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Eu1 O1 3_667 2.367(5) y
Eu1 O3 . 2.389(5) y
Eu1 O4 3_667 2.406(5) y
Eu1 O6 . 2.477(6) y
Eu1 O5 . 2.488(6) y
Eu1 O2 . 2.503(5) y
Eu1 O1 . 2.578(5) y
Eu1 N2 . 2.578(7) y
Eu1 N1 . 2.635(6) y
Eu1 Eu1 3_667 3.9700(9) n
N1 C37 . 1.309(10) ?
N1 C41 . 1.362(10) ?
N2 C46 . 1.315(11) ?
N2 C42 . 1.345(10) ?
N3 C49 . 1.304(16) ?
N3 C51 . 1.420(14) ?
N3 C50 . 1.434(14) ?
O1 C1 . 1.278(8) ?
O1 Eu1 3_667 2.367(5) ?
O2 C1 . 1.233(9) ?
O3 C13 . 1.242(9) ?
O4 C13 . 1.259(9) ?
O4 Eu1 3_667 2.406(5) ?
O5 C25 . 1.234(10) ?
O6 C25 . 1.247(10) ?
O7 C49 . 1.250(15) ?
C1 C2 . 1.504(10) ?
C2 C3 . 1.500(11) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.331(12) ?
C3 C8 . 1.410(13) ?
C4 C5 . 1.406(12) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.335(13) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.385(13) ?
C6 H6 . 0.9300 ?
C7 C12 . 1.395(14) ?
C7 C8 . 1.434(12) ?
C8 C9 . 1.390(13) ?
C9 C10 . 1.356(13) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.411(15) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.334(15) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 C14 . 1.516(10) ?
C14 C15 . 1.513(12) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C16 . 1.362(13) ?
C15 C20 . 1.409(13) ?
C16 C17 . 1.407(13) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.347(14) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.383(14) ?
C18 H18 . 0.9300 ?
C19 C24 . 1.384(14) ?
C19 C20 . 1.444(13) ?
C20 C21 . 1.401(13) ?
C21 C22 . 1.370(13) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.407(15) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.343(15) ?
C23 H23 . 0.9300 ?
C24 H24 . 0.9300 ?
C25 C26 . 1.533(12) ?
C26 C27 . 1.481(13) ?
C26 H26A . 0.9700 ?
C26 H26B . 0.9700 ?
C27 C28 . 1.381(14) ?
C27 C32 . 1.409(15) ?
C28 C29 . 1.410(16) ?
C28 H28 . 0.9300 ?
C29 C30 . 1.317(17) ?
C29 H29 . 0.9300 ?
C30 C31 . 1.373(18) ?
C30 H30 . 0.9300 ?
C31 C32 . 1.418(16) ?
C31 C36 . 1.418(18) ?
C32 C33 . 1.419(15) ?
C33 C34 . 1.393(15) ?
C33 H33 . 0.9300 ?
C34 C35 . 1.358(16) ?
C34 H34 . 0.9300 ?
C35 C36 . 1.294(17) ?
C35 H35 . 0.9300 ?
C36 H36 . 0.9300 ?
C37 C38 . 1.424(11) ?
C37 H37 . 0.9300 ?
C38 C39 . 1.353(12) ?
C38 H38 . 0.9300 ?
C39 C40 . 1.391(12) ?
C39 H39 . 0.9300 ?
C40 C41 . 1.395(11) ?
C40 C47 . 1.421(12) ?
C41 C42 . 1.427(12) ?
C42 C43 . 1.417(12) ?
C43 C44 . 1.403(14) ?
C43 C48 . 1.416(14) ?
C44 C45 . 1.342(14) ?
C44 H44 . 0.9300 ?
C45 C46 . 1.388(12) ?
C45 H45 . 0.9300 ?
C46 H46 . 0.9300 ?
C47 C48 . 1.324(13) ?
C47 H47 . 0.9300 ?
C48 H48 . 0.9300 ?
C49 H49 . 0.9300 ?
C50 H50A . 0.9600 ?
C50 H50B . 0.9600 ?
C50 H50C . 0.9600 ?
C51 H51A . 0.9600 ?
C51 H51B . 0.9600 ?
C51 H51C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C6 H6 O7 3_566 0.93 2.58 3.469(15) 160.6
C37 H37 O4 3_667 0.93 2.38 3.053(10) 129.5
C46 H46 O3 . 0.93 2.48 3.096(11) 124.1
C47 H47 O2 3_567 0.93 2.46 3.314(11) 152.4
C50 H50A O6 1_554 0.96 2.60 3.397(14) 140.1
C18 H18 Cg1 2_655 0.93 2.91 3.682(13) 141
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
O1 Eu1 N1 C37 3_667 . 28.0(9)
O3 Eu1 N1 C37 . . -148.6(6)
O4 Eu1 N1 C37 3_667 . -2.8(6)
O6 Eu1 N1 C37 . . 84.6(7)
O5 Eu1 N1 C37 . . 124.3(6)
O2 Eu1 N1 C37 . . -99.7(7)
O1 Eu1 N1 C37 . . -66.6(7)
N2 Eu1 N1 C37 . . -180.0(7)
Eu1 Eu1 N1 C37 3_667 . -39.1(7)
O1 Eu1 N1 C41 3_667 . -154.3(5)
O3 Eu1 N1 C41 . . 29.1(7)
O4 Eu1 N1 C41 3_667 . 175.0(6)
O6 Eu1 N1 C41 . . -97.7(6)
O5 Eu1 N1 C41 . . -58.0(6)
O2 Eu1 N1 C41 . . 78.1(6)
O1 Eu1 N1 C41 . . 111.1(6)
N2 Eu1 N1 C41 . . -2.2(6)
Eu1 Eu1 N1 C41 3_667 . 138.6(5)
O1 Eu1 N2 C46 3_667 . -23.9(9)
O3 Eu1 N2 C46 . . 20.7(7)
O4 Eu1 N2 C46 3_667 . 175.1(6)
O6 Eu1 N2 C46 . . -105.4(7)
O5 Eu1 N2 C46 . . -55.1(7)
O2 Eu1 N2 C46 . . 100.6(7)
O1 Eu1 N2 C46 . . 78.4(7)
N1 Eu1 N2 C46 . . 179.2(8)
Eu1 Eu1 N2 C46 3_667 . 42.4(8)
O1 Eu1 N2 C42 3_667 . 160.1(6)
O3 Eu1 N2 C42 . . -155.3(7)
O4 Eu1 N2 C42 3_667 . -0.9(8)
O6 Eu1 N2 C42 . . 78.6(7)
O5 Eu1 N2 C42 . . 128.9(7)
O2 Eu1 N2 C42 . . -75.5(7)
O1 Eu1 N2 C42 . . -97.7(7)
N1 Eu1 N2 C42 . . 3.2(6)
Eu1 Eu1 N2 C42 3_667 . -133.6(6)
O1 Eu1 O1 C1 3_667 . 161.2(5)
O3 Eu1 O1 C1 . . 82.3(4)
O4 Eu1 O1 C1 3_667 . -117.3(4)
O6 Eu1 O1 C1 . . -152.9(5)
O5 Eu1 O1 C1 . . 114.7(5)
O2 Eu1 O1 C1 . . -8.5(4)
N2 Eu1 O1 C1 . . 19.3(5)
N1 Eu1 O1 C1 . . -50.5(5)
Eu1 Eu1 O1 C1 3_667 . 161.2(5)
O1 Eu1 O1 Eu1 3_667 3_667 0.0
O3 Eu1 O1 Eu1 . 3_667 -78.9(2)
O4 Eu1 O1 Eu1 3_667 3_667 81.4(2)
O6 Eu1 O1 Eu1 . 3_667 45.8(5)
O5 Eu1 O1 Eu1 . 3_667 -46.5(3)
O2 Eu1 O1 Eu1 . 3_667 -169.7(3)
N2 Eu1 O1 Eu1 . 3_667 -141.9(2)
N1 Eu1 O1 Eu1 . 3_667 148.3(2)
O1 Eu1 O2 C1 3_667 . -3.0(5)
O3 Eu1 O2 C1 . . -63.9(5)
O4 Eu1 O2 C1 3_667 . 73.1(5)
O6 Eu1 O2 C1 . . 156.4(5)
O5 Eu1 O2 C1 . . -109.9(5)
O1 Eu1 O2 C1 . . 8.8(4)
N2 Eu1 O2 C1 . . -146.3(5)
N1 Eu1 O2 C1 . . 148.4(5)
Eu1 Eu1 O2 C1 3_667 . 3.0(4)
O1 Eu1 O3 C13 3_667 . -17.2(9)
O4 Eu1 O3 C13 3_667 . 33.2(10)
O6 Eu1 O3 C13 . . -90.6(9)
O5 Eu1 O3 C13 . . -96.4(9)
O2 Eu1 O3 C13 . . 113.5(9)
O1 Eu1 O3 C13 . . 60.8(9)
N2 Eu1 O3 C13 . . -171.0(9)
N1 Eu1 O3 C13 . . 161.1(8)
Eu1 Eu1 O3 C13 3_667 . 23.1(9)
O1 Eu1 O5 C25 3_667 . 99.6(6)
O3 Eu1 O5 C25 . . 176.9(6)
O4 Eu1 O5 C25 3_667 . 40.2(6)
O6 Eu1 O5 C25 . . 2.9(5)
O2 Eu1 O5 C25 . . -135.9(5)
O1 Eu1 O5 C25 . . 145.5(5)
N2 Eu1 O5 C25 . . -99.3(6)
N1 Eu1 O5 C25 . . -49.1(6)
Eu1 Eu1 O5 C25 3_667 . 119.6(5)
O1 Eu1 O6 C25 3_667 . -77.3(5)
O3 Eu1 O6 C25 . . -9.9(6)
O4 Eu1 O6 C25 3_667 . -154.6(5)
O5 Eu1 O6 C25 . . -2.9(5)
O2 Eu1 O6 C25 . . 119.8(6)
O1 Eu1 O6 C25 . . -120.9(6)
N2 Eu1 O6 C25 . . 65.9(5)
N1 Eu1 O6 C25 . . 127.7(6)
Eu1 Eu1 O6 C25 3_667 . -92.0(5)
Eu1 O2 C1 O1 . . -16.4(8)
Eu1 O2 C1 C2 . . 162.8(7)
Eu1 O1 C1 O2 3_667 . 149.4(9)
Eu1 O1 C1 O2 . . 15.8(7)
Eu1 O1 C1 C2 3_667 . -29.9(16)
Eu1 O1 C1 C2 . . -163.4(6)
O2 C1 C2 C3 . . -4.3(12)
O1 C1 C2 C3 . . 174.9(8)
C1 C2 C3 C4 . . 111.3(10)
C1 C2 C3 C8 . . -70.9(11)
C8 C3 C4 C5 . . 1.4(15)
C2 C3 C4 C5 . . 179.4(9)
C3 C4 C5 C6 . . 0.4(16)
C4 C5 C6 C7 . . -2.2(16)
C5 C6 C7 C12 . . -178.3(11)
C5 C6 C7 C8 . . 2.1(15)
C4 C3 C8 C9 . . -179.9(9)
C2 C3 C8 C9 . . 2.2(14)
C4 C3 C8 C7 . . -1.5(14)
C2 C3 C8 C7 . . -179.4(8)
C6 C7 C8 C9 . . 178.3(9)
C12 C7 C8 C9 . . -1.4(14)
C6 C7 C8 C3 . . -0.2(14)
C12 C7 C8 C3 . . -179.9(9)
C3 C8 C9 C10 . . 180.0(10)
C7 C8 C9 C10 . . 1.5(16)
C8 C9 C10 C11 . . -1.6(18)
C9 C10 C11 C12 . . 2(2)
C10 C11 C12 C7 . . -1(2)
C6 C7 C12 C11 . . -178.3(11)
C8 C7 C12 C11 . . 1.4(17)
Eu1 O3 C13 O4 . . -30.2(15)
Eu1 O3 C13 C14 . . 151.8(6)
Eu1 O4 C13 O3 3_667 . 10.3(13)
Eu1 O4 C13 C14 3_667 . -171.7(5)
O3 C13 C14 C15 . . -139.8(9)
O4 C13 C14 C15 . . 42.0(12)
C13 C14 C15 C16 . . -119.9(10)
C13 C14 C15 C20 . . 63.7(12)
C20 C15 C16 C17 . . -1.1(15)
C14 C15 C16 C17 . . -177.6(9)
C15 C16 C17 C18 . . 0.9(17)
C16 C17 C18 C19 . . 1.7(17)
C17 C18 C19 C24 . . 176.8(11)
C17 C18 C19 C20 . . -3.9(17)
C16 C15 C20 C21 . . -177.7(10)
C14 C15 C20 C21 . . -1.3(14)
C16 C15 C20 C19 . . -1.2(14)
C14 C15 C20 C19 . . 175.3(8)
C18 C19 C20 C21 . . -179.7(9)
C24 C19 C20 C21 . . -0.3(14)
C18 C19 C20 C15 . . 3.5(14)
C24 C19 C20 C15 . . -177.1(9)
C15 C20 C21 C22 . . 175.8(10)
C19 C20 C21 C22 . . -0.8(15)
C20 C21 C22 C23 . . 1.1(17)
C21 C22 C23 C24 . . -0.1(18)
C22 C23 C24 C19 . . -1.1(19)
C18 C19 C24 C23 . . -179.3(12)
C20 C19 C24 C23 . . 1.4(17)
Eu1 O5 C25 O6 . . -5.4(10)
Eu1 O5 C25 C26 . . 173.2(7)
Eu1 O6 C25 O5 . . 5.4(10)
Eu1 O6 C25 C26 . . -173.1(8)
O5 C25 C26 C27 . . -52.7(13)
O6 C25 C26 C27 . . 125.9(11)
C25 C26 C27 C28 . . 107.6(11)
C25 C26 C27 C32 . . -69.9(13)
C32 C27 C28 C29 . . -0.5(15)
C26 C27 C28 C29 . . -178.2(10)
C27 C28 C29 C30 . . 2.1(19)
C28 C29 C30 C31 . . -2(2)
C29 C30 C31 C32 . . 0(2)
C29 C30 C31 C36 . . 179.9(13)
C28 C27 C32 C31 . . -1.3(16)
C26 C27 C32 C31 . . 176.3(10)
C28 C27 C32 C33 . . 178.0(10)
C26 C27 C32 C33 . . -4.3(16)
C30 C31 C32 C27 . . 1.7(17)
C36 C31 C32 C27 . . -178.3(11)
C30 C31 C32 C33 . . -177.7(11)
C36 C31 C32 C33 . . 2.4(17)
C27 C32 C33 C34 . . 178.6(10)
C31 C32 C33 C34 . . -2.0(16)
C32 C33 C34 C35 . . 0.0(17)
C33 C34 C35 C36 . . 2(2)
C34 C35 C36 C31 . . -2(2)
C30 C31 C36 C35 . . 179.4(13)
C32 C31 C36 C35 . . -1(2)
C41 N1 C37 C38 . . 0.4(13)
Eu1 N1 C37 C38 . . 178.1(7)
N1 C37 C38 C39 . . -0.2(14)
C37 C38 C39 C40 . . -0.2(14)
C38 C39 C40 C41 . . 0.2(14)
C38 C39 C40 C47 . . -179.4(9)
C37 N1 C41 C40 . . -0.3(12)
Eu1 N1 C41 C40 . . -178.1(6)
C37 N1 C41 C42 . . 179.1(8)
Eu1 N1 C41 C42 . . 1.3(10)
C39 C40 C41 N1 . . 0.0(14)
C47 C40 C41 N1 . . 179.6(8)
C39 C40 C41 C42 . . -179.4(8)
C47 C40 C41 C42 . . 0.2(13)
C46 N2 C42 C43 . . 0.6(14)
Eu1 N2 C42 C43 . . 176.7(7)
C46 N2 C42 C41 . . 179.9(8)
Eu1 N2 C42 C41 . . -4.0(11)
N1 C41 C42 N2 . . 1.7(12)
C40 C41 C42 N2 . . -178.9(8)
N1 C41 C42 C43 . . -179.0(8)
C40 C41 C42 C43 . . 0.4(13)
N2 C42 C43 C44 . . -0.9(15)
C41 C42 C43 C44 . . 179.9(9)
N2 C42 C43 C48 . . 178.5(9)
C41 C42 C43 C48 . . -0.8(14)
C48 C43 C44 C45 . . -178.5(11)
C42 C43 C44 C45 . . 0.8(16)
C43 C44 C45 C46 . . -0.5(18)
C42 N2 C46 C45 . . -0.3(15)
Eu1 N2 C46 C45 . . -176.4(8)
C44 C45 C46 N2 . . 0.2(18)
C39 C40 C47 C48 . . 179.1(10)
C41 C40 C47 C48 . . -0.5(15)
C40 C47 C48 C43 . . 0.1(16)
C44 C43 C48 C47 . . 179.8(11)
C42 C43 C48 C47 . . 0.5(16)
C51 N3 C49 O7 . . -3(2)
C50 N3 C49 O7 . . 177.8(13)
