#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/92/2009236.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_2009236
loop_
_publ_author_name
'Ward, Michael D.'
'McCleverty, Jon A.'
'Mann, Karen L. V.'
'Jeffery, John C.'
'Motson, Graham R.'
'Hurst, Joanne'
_publ_section_title
;
 Ternary lanthanide complexes of
 hydrotris[3-(2-pyridyl)pyrazol-1-yl]borate (Tppy) and anionic
 O,O-bidentate chelates: [Tb(Tppy)(dbm)₂] and
 [Eu(Tppy)(trop)(NO₃)] (Hdbm is dibenzoylmethane and Htrop is
 tropolone)
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2055
_journal_page_last               2058
_journal_paper_doi               10.1107/S0108270199011051
_journal_volume                  55
_journal_year                    1999
_chemical_formula_iupac
'[Eu(C7 H5 O2 )(NO3 )(C24 H19 BN9 )] , CH2 Cl2 '
_chemical_formula_moiety         'C31 H24 BEuN10 O5 , CH2 Cl2 '
_chemical_formula_sum            'C32 H26 B Cl2 Eu N10 O5'
_chemical_formula_weight         864.30
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                85.895(9)
_cell_angle_beta                 72.163(10)
_cell_angle_gamma                78.536(8)
_cell_formula_units_Z            2
_cell_length_a                   10.2193(19)
_cell_length_b                   10.9574(12)
_cell_length_c                   15.994(3)
_cell_measurement_reflns_used    264
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3
_cell_volume                     1670.7(5)
_computing_cell_refinement       'SAINT (Siemens, 1995a)'
_computing_data_collection       'SMART (Siemens, 1995a)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Siemens, 1995b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'Siemens Smart area detector'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0535
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17128
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.90
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    2.095
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.685
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS: Sheldrick, 1996)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.883
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         7546
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0279
_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)+(0.0243P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0581
_reflns_number_gt                6396
_reflns_number_total             7546
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf1328.cif
_cod_data_source_block           2
_cod_original_cell_volume        1670.8(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2009236
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Eu1 0.699430(16) 0.669296(13) 0.733875(10) 0.01520(5) Uani d . 1 . . Eu
B1 1.0027(4) 0.4951(3) 0.8117(2) 0.0218(8) Uani d . 1 . . B
H1 1.0818 0.4478 0.8322 0.026 Uiso calc R 1 . . H
N11 1.0246(2) 0.6302(2) 0.78485(16) 0.0199(5) Uani d . 1 . . N
N12 0.9193(2) 0.7131(2) 0.76562(16) 0.0196(5) Uani d . 1 . . N
C13 0.9561(3) 0.8252(3) 0.75966(19) 0.0196(6) Uani d . 1 . . C
C14 1.0879(3) 0.8142(3) 0.7720(2) 0.0261(7) Uani d . 1 . . C
H14 1.1394 0.8784 0.7691 0.031 Uiso calc R 1 . . H
C15 1.1263(3) 0.6890(3) 0.7893(2) 0.0249(7) Uani d . 1 . . C
H15 1.2101 0.6509 0.8021 0.030 Uiso calc R 1 . . H
N21 0.7168(3) 0.9137(2) 0.77879(16) 0.0203(5) Uani d . 1 . . N
C22 0.8496(3) 0.9354(3) 0.75532(19) 0.0194(6) Uani d . 1 . . C
C23 0.8809(3) 1.0534(3) 0.7340(2) 0.0265(7) Uani d . 1 . . C
H23 0.9753 1.0649 0.7163 0.032 Uiso calc R 1 . . H
C24 0.7729(4) 1.1540(3) 0.7388(2) 0.0300(8) Uani d . 1 . . C
H24 0.7921 1.2355 0.7243 0.036 Uiso calc R 1 . . H
C25 0.6370(4) 1.1344(3) 0.7651(2) 0.0272(7) Uani d . 1 . . C
H25 0.5608 1.2020 0.7703 0.033 Uiso calc R 1 . . H
C26 0.6145(3) 1.0133(3) 0.7838(2) 0.0234(7) Uani d . 1 . . C
H26 0.5207 1.0001 0.8013 0.028 Uiso calc R 1 . . H
N31 0.8633(2) 0.5057(2) 0.88657(16) 0.0207(5) Uani d . 1 . . N
N32 0.7442(2) 0.5754(2) 0.87442(16) 0.0191(5) Uani d . 1 . . N
C33 0.6515(3) 0.5952(3) 0.95333(19) 0.0187(6) Uani d . 1 . . C
C34 0.7089(3) 0.5374(3) 1.0188(2) 0.0244(7) Uani d . 1 . . C
H34 0.6651 0.5368 1.0804 0.029 Uiso calc R 1 . . H
C35 0.8421(3) 0.4823(3) 0.9739(2) 0.0244(7) Uani d . 1 . . C
H35 0.9090 0.4353 0.9996 0.029 Uiso calc R 1 . . H
N41 0.4984(2) 0.7193(2) 0.88074(16) 0.0189(5) Uani d . 1 . . N
C42 0.5150(3) 0.6746(3) 0.95906(19) 0.0194(6) Uani d . 1 . . C
C43 0.4109(3) 0.7026(3) 1.0377(2) 0.0263(7) Uani d . 1 . . C
H43 0.4257 0.6705 1.0915 0.032 Uiso calc R 1 . . H
C44 0.2857(3) 0.7774(3) 1.0374(2) 0.0310(8) Uani d . 1 . . C
H44 0.2135 0.7979 1.0910 0.037 Uiso calc R 1 . . H
C45 0.2664(3) 0.8223(3) 0.9580(2) 0.0267(7) Uani d . 1 . . C
H45 0.1804 0.8731 0.9560 0.032 Uiso calc R 1 . . H
C46 0.3746(3) 0.7917(3) 0.8819(2) 0.0234(7) Uani d . 1 . . C
H46 0.3612 0.8232 0.8276 0.028 Uiso calc R 1 . . H
N51 0.9943(2) 0.4332(2) 0.73093(16) 0.0187(5) Uani d . 1 . . N
N52 0.8983(2) 0.4856(2) 0.68950(16) 0.0184(5) Uani d . 1 . . N
C53 0.9251(3) 0.4186(3) 0.61749(19) 0.0184(6) Uani d . 1 . . C
C54 1.0406(3) 0.3219(3) 0.6114(2) 0.0227(7) Uani d . 1 . . C
H54 1.0820 0.2612 0.5667 0.027 Uiso calc R 1 . . H
C55 1.0800(3) 0.3351(3) 0.6844(2) 0.0240(7) Uani d . 1 . . C
H55 1.1556 0.2833 0.6998 0.029 Uiso calc R 1 . . H
N61 0.7301(2) 0.5515(2) 0.58812(16) 0.0187(5) Uani d . 1 . . N
C62 0.8362(3) 0.4547(3) 0.55996(19) 0.0182(6) Uani d . 1 . . C
C63 0.8599(3) 0.3932(3) 0.48192(19) 0.0224(7) Uani d . 1 . . C
H63 0.9356 0.3252 0.4637 0.027 Uiso calc R 1 . . H
C64 0.7706(3) 0.4335(3) 0.4316(2) 0.0262(7) Uani d . 1 . . C
H64 0.7834 0.3925 0.3785 0.031 Uiso calc R 1 . . H
C65 0.6632(3) 0.5333(3) 0.4589(2) 0.0257(7) Uani d . 1 . . C
H65 0.6018 0.5632 0.4247 0.031 Uiso calc R 1 . . H
C66 0.6462(3) 0.5892(3) 0.5374(2) 0.0211(6) Uani d . 1 . . C
H66 0.5715 0.6578 0.5563 0.025 Uiso calc R 1 . . H
O21 0.5467(2) 0.82552(17) 0.68007(13) 0.0215(5) Uani d . 1 . . O
O22 0.8134(2) 0.78716(17) 0.60875(13) 0.0203(4) Uani d . 1 . . O
C71 0.7453(3) 0.8869(3) 0.58381(19) 0.0200(6) Uani d . 1 . . C
C72 0.5928(3) 0.9098(3) 0.62560(19) 0.0198(6) Uani d . 1 . . C
C73 0.4966(3) 1.0168(3) 0.6131(2) 0.0274(7) Uani d . 1 . . C
H73 0.4018 1.0161 0.6455 0.033 Uiso calc R 1 . . H
C74 0.5179(4) 1.1219(3) 0.5617(2) 0.0353(9) Uani d . 1 . . C
H74 0.4363 1.1836 0.5664 0.042 Uiso calc R 1 . . H
C75 0.6400(4) 1.1510(3) 0.5044(3) 0.0413(10) Uani d . 1 . . C
H75 0.6316 1.2291 0.4748 0.050 Uiso calc R 1 . . H
C76 0.7723(4) 1.0794(3) 0.4856(2) 0.0356(9) Uani d . 1 . . C
H76 0.8428 1.1138 0.4424 0.043 Uiso calc R 1 . . H
C77 0.8186(3) 0.9644(3) 0.5200(2) 0.0260(7) Uani d . 1 . . C
H77 0.9159 0.9328 0.4965 0.031 Uiso calc R 1 . . H
O11 0.4653(2) 0.60489(18) 0.72646(13) 0.0224(5) Uani d . 1 . . O
O12 0.6059(2) 0.46233(19) 0.77245(14) 0.0243(5) Uani d . 1 . . O
O13 0.4170(2) 0.4188(2) 0.75393(16) 0.0337(6) Uani d . 1 . . O
N1 0.4947(3) 0.4939(2) 0.75073(16) 0.0200(5) Uani d . 1 . . N
C99 1.2415(5) 0.1763(4) 0.9171(3) 0.0671(14) Uani d D 1 . . C
H99A 1.2526 0.2628 0.8988 0.081 Uiso calc PR 0.844(4) A 1 H
H99B 1.3339 0.1295 0.9190 0.081 Uiso calc PR 0.844(4) A 1 H
H9A' 1.3290 0.1640 0.8675 0.081 Uiso calc PR 0.156(4) A 2 H
H9B' 1.2129 0.2673 0.9266 0.081 Uiso calc PR 0.156(4) A 2 H
Cl1 1.12758(16) 0.17953(13) 1.02145(9) 0.0552(5) Uani d PD 0.844(4) A 1 Cl
Cl2 1.1959(3) 0.11259(13) 0.83879(12) 0.0739(8) Uani d PD 0.844(4) A 1 Cl
Cl1' 1.284(3) 0.1174(14) 1.0032(11) 0.229(17) Uani d PD 0.156(4) A 2 Cl
Cl2' 1.1099(9) 0.1300(9) 0.8779(9) 0.087(4) Uani d PD 0.156(4) A 2 Cl
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'
B B 0.0013 0.0007 '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'
Cl Cl 0.1484 0.1585 '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_publ_flag
O21 Eu1 O22 64.89(7) yes
O21 Eu1 N52 143.84(7) ?
O22 Eu1 N52 90.31(7) ?
O21 Eu1 N32 142.58(7) ?
O22 Eu1 N32 137.85(7) ?
N52 Eu1 N32 73.36(8) yes
O21 Eu1 N12 122.52(7) ?
O22 Eu1 N12 74.32(7) ?
N52 Eu1 N12 69.72(8) yes
N32 Eu1 N12 63.61(8) yes
O21 Eu1 O12 112.58(7) ?
O22 Eu1 O12 140.84(7) ?
N52 Eu1 O12 69.77(7) ?
N32 Eu1 O12 69.64(7) ?
N12 Eu1 O12 124.57(7) ?
O21 Eu1 N41 81.42(7) ?
O22 Eu1 N41 136.20(7) ?
N52 Eu1 N41 131.38(7) yes
N32 Eu1 N41 62.32(7) yes
N12 Eu1 N41 104.70(8) yes
O12 Eu1 N41 76.69(7) ?
O21 Eu1 N61 84.16(7) ?
O22 Eu1 N61 70.92(7) ?
N52 Eu1 N61 62.18(7) yes
N32 Eu1 N61 127.57(7) yes
N12 Eu1 N61 119.04(8) yes
O12 Eu1 N61 69.96(7) ?
N41 Eu1 N61 134.86(7) yes
O21 Eu1 O11 64.28(6) yes
O22 Eu1 O11 115.05(6) ?
N52 Eu1 O11 108.97(7) ?
N32 Eu1 O11 107.03(7) ?
N12 Eu1 O11 170.63(7) ?
O12 Eu1 O11 48.31(6) ?
N41 Eu1 O11 68.86(7) ?
N61 Eu1 O11 66.32(7) ?
O21 Eu1 N21 68.98(7) ?
O22 Eu1 N21 66.89(7) ?
N52 Eu1 N21 126.90(7) yes
N32 Eu1 N21 91.98(7) yes
N12 Eu1 N21 58.34(7) yes
O12 Eu1 N21 151.61(7) ?
N41 Eu1 N21 75.58(7) yes
N61 Eu1 N21 136.50(7) yes
O11 Eu1 N21 124.08(6) ?
O21 Eu1 N1 88.40(7) ?
O22 Eu1 N1 130.22(7) ?
N52 Eu1 N1 88.77(7) ?
N32 Eu1 N1 88.91(7) ?
N12 Eu1 N1 148.60(7) ?
O12 Eu1 N1 24.18(6) ?
N41 Eu1 N1 72.11(7) ?
N61 Eu1 N1 64.92(7) ?
O11 Eu1 N1 24.17(6) ?
N21 Eu1 N1 142.88(7) ?
O21 Eu1 C72 19.67(7) ?
O22 Eu1 C72 45.89(7) ?
N52 Eu1 C72 132.38(8) ?
N32 Eu1 C72 149.54(8) ?
N12 Eu1 C72 106.03(7) ?
O12 Eu1 C72 129.19(7) ?
N41 Eu1 C72 96.10(7) ?
N61 Eu1 C72 82.83(7) ?
O11 Eu1 C72 81.83(7) ?
N21 Eu1 C72 60.37(7) ?
N1 Eu1 C72 105.37(7) ?
N51 B1 N31 111.0(2) ?
N51 B1 N11 107.5(2) ?
N31 B1 N11 106.5(2) ?
C15 N11 N12 110.3(2) ?
C15 N11 B1 130.1(2) ?
N12 N11 B1 118.8(2) ?
C13 N12 N11 106.1(2) ?
C13 N12 Eu1 125.22(18) ?
N11 N12 Eu1 128.53(17) ?
N12 C13 C14 110.6(3) ?
N12 C13 C22 117.6(3) ?
C14 C13 C22 131.1(3) ?
C15 C14 C13 104.6(3) ?
N11 C15 C14 108.4(3) ?
C26 N21 C22 116.8(2) ?
C26 N21 Eu1 123.40(19) ?
C22 N21 Eu1 113.52(17) ?
N21 C22 C23 122.6(3) ?
N21 C22 C13 114.5(2) ?
C23 C22 C13 122.8(3) ?
C24 C23 C22 119.1(3) ?
C25 C24 C23 119.1(3) ?
C24 C25 C26 118.3(3) ?
N21 C26 C25 124.1(3) ?
C35 N31 N32 109.0(2) ?
C35 N31 B1 128.9(2) ?
N32 N31 B1 119.9(2) ?
C33 N32 N31 107.0(2) ?
C33 N32 Eu1 123.54(18) ?
N31 N32 Eu1 129.30(18) ?
N32 C33 C34 110.5(3) ?
N32 C33 C42 118.0(2) ?
C34 C33 C42 131.4(3) ?
C35 C34 C33 104.6(3) ?
N31 C35 C34 108.9(3) ?
C46 N41 C42 117.4(3) ?
C46 N41 Eu1 121.25(19) ?
C42 N41 Eu1 121.32(18) ?
N41 C42 C43 122.1(3) ?
N41 C42 C33 114.8(3) ?
C43 C42 C33 123.1(3) ?
C44 C43 C42 119.5(3) ?
C43 C44 C45 119.1(3) ?
C46 C45 C44 118.6(3) ?
N41 C46 C45 123.2(3) ?
C55 N51 N52 109.4(2) ?
C55 N51 B1 129.8(2) ?
N52 N51 B1 120.4(2) ?
C53 N52 N51 106.8(2) ?
C53 N52 Eu1 123.64(18) ?
N51 N52 Eu1 129.57(18) ?
N52 C53 C54 110.3(3) ?
N52 C53 C62 118.5(3) ?
C54 C53 C62 131.2(3) ?
C55 C54 C53 104.3(3) ?
N51 C55 C54 109.2(3) ?
C66 N61 C62 117.5(3) ?
C66 N61 Eu1 121.8(2) ?
C62 N61 Eu1 120.56(18) ?
N61 C62 C63 122.6(3) ?
N61 C62 C53 115.1(3) ?
C63 C62 C53 122.3(3) ?
C64 C63 C62 118.4(3) ?
C65 C64 C63 119.5(3) ?
C64 C65 C66 118.6(3) ?
N61 C66 C65 123.3(3) ?
C72 O21 Eu1 121.65(18) ?
C71 O22 Eu1 120.39(18) ?
O22 C71 C77 119.2(3) ?
O22 C71 C72 115.5(2) ?
C77 C71 C72 125.3(3) ?
O22 C71 Eu1 39.76(13) ?
C77 C71 Eu1 157.7(2) ?
C72 C71 Eu1 76.27(15) ?
O21 C72 C73 118.7(3) ?
O21 C72 C71 115.3(2) ?
C73 C72 C71 126.0(3) ?
O21 C72 Eu1 38.68(13) ?
C73 C72 Eu1 154.5(2) ?
C71 C72 Eu1 77.52(15) ?
C74 C73 C72 130.7(3) ?
C73 C74 C75 129.8(3) ?
C76 C75 C74 127.3(3) ?
C75 C76 C77 129.9(3) ?
C76 C77 C71 130.8(3) ?
N1 O11 Eu1 95.60(15) ?
N1 O12 Eu1 98.62(15) ?
O13 N1 O11 121.3(2) ?
O13 N1 O12 121.4(2) ?
O11 N1 O12 117.3(2) ?
O13 N1 Eu1 176.5(2) ?
O11 N1 Eu1 60.23(13) ?
O12 N1 Eu1 57.20(13) ?
Cl1' C99 Cl2 132.2(5) ?
Cl1' C99 Cl1 55.4(11) ?
Cl2 C99 Cl1 116.3(3) ?
Cl1' C99 Cl2' 124.4(7) ?
Cl2 C99 Cl2' 29.6(4) ?
Cl1 C99 Cl2' 88.5(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 O21 . 2.3784(18) yes
Eu1 O22 . 2.414(2) yes
Eu1 N52 . 2.526(2) yes
Eu1 N32 . 2.536(2) yes
Eu1 N12 . 2.588(2) yes
Eu1 O12 . 2.596(2) yes
Eu1 N41 . 2.611(2) yes
Eu1 N61 . 2.650(2) yes
Eu1 O11 . 2.663(2) yes
Eu1 N21 . 2.875(2) yes
Eu1 N1 . 3.053(3) ?
Eu1 C72 . 3.239(3) ?
B1 N51 . 1.534(4) ?
B1 N31 . 1.545(4) ?
B1 N11 . 1.553(4) ?
N11 C15 . 1.348(4) ?
N11 N12 . 1.361(3) ?
N12 C13 . 1.344(4) ?
C13 C14 . 1.401(4) ?
C13 C22 . 1.470(4) ?
C14 C15 . 1.382(4) ?
N21 C26 . 1.341(4) ?
N21 C22 . 1.357(4) ?
C22 C23 . 1.387(4) ?
C23 C24 . 1.385(4) ?
C24 C25 . 1.378(5) ?
C25 C26 . 1.388(4) ?
N31 C35 . 1.360(4) ?
N31 N32 . 1.363(3) ?
N32 C33 . 1.328(4) ?
C33 C34 . 1.406(4) ?
C33 C42 . 1.470(4) ?
C34 C35 . 1.367(4) ?
N41 C46 . 1.349(4) ?
N41 C42 . 1.359(4) ?
C42 C43 . 1.383(4) ?
C43 C44 . 1.376(4) ?
C44 C45 . 1.386(4) ?
C45 C46 . 1.380(4) ?
N51 C55 . 1.348(4) ?
N51 N52 . 1.360(3) ?
N52 C53 . 1.337(4) ?
C53 C54 . 1.404(4) ?
C53 C62 . 1.465(4) ?
C54 C55 . 1.372(4) ?
N61 C66 . 1.342(4) ?
N61 C62 . 1.347(4) ?
C62 C63 . 1.393(4) ?
C63 C64 . 1.384(4) ?
C64 C65 . 1.374(4) ?
C65 C66 . 1.384(4) ?
O21 C72 . 1.281(3) ?
O22 C71 . 1.282(3) ?
C71 C77 . 1.408(4) ?
C71 C72 . 1.473(4) ?
C72 C73 . 1.418(4) ?
C73 C74 . 1.379(4) ?
C74 C75 . 1.384(5) ?
C75 C76 . 1.377(5) ?
C76 C77 . 1.392(4) ?
O11 N1 . 1.256(3) ?
O12 N1 . 1.265(3) ?
O13 N1 . 1.241(3) ?
C99 Cl1' . 1.623(11) ?
C99 Cl2 . 1.698(5) ?
C99 Cl1 . 1.716(4) ?
C99 Cl2' . 1.813(10) ?
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
N51 B1 N11 C15 -124.0(3)
N31 B1 N11 C15 116.9(3)
N51 B1 N11 N12 67.3(3)
N31 B1 N11 N12 -51.8(3)
C15 N11 N12 C13 -1.1(3)
B1 N11 N12 C13 169.7(3)
C15 N11 N12 Eu1 174.5(2)
B1 N11 N12 Eu1 -14.7(4)
O21 Eu1 N12 C13 4.5(3)
O22 Eu1 N12 C13 50.0(2)
N52 Eu1 N12 C13 146.3(3)
N32 Eu1 N12 C13 -132.8(3)
O12 Eu1 N12 C13 -168.4(2)
N41 Eu1 N12 C13 -84.6(2)
N61 Eu1 N12 C13 107.0(2)
O11 Eu1 N12 C13 -130.1(4)
N21 Eu1 N12 C13 -22.2(2)
N1 Eu1 N12 C13 -164.2(2)
C72 Eu1 N12 C13 16.3(2)
O21 Eu1 N12 N11 -170.2(2)
O22 Eu1 N12 N11 -124.8(2)
N52 Eu1 N12 N11 -28.5(2)
N32 Eu1 N12 N11 52.4(2)
O12 Eu1 N12 N11 16.9(3)
N41 Eu1 N12 N11 100.7(2)
N61 Eu1 N12 N11 -67.8(2)
O11 Eu1 N12 N11 55.2(5)
N21 Eu1 N12 N11 163.0(3)
N1 Eu1 N12 N11 21.0(3)
C72 Eu1 N12 N11 -158.4(2)
N11 N12 C13 C14 2.1(3)
Eu1 N12 C13 C14 -173.6(2)
N11 N12 C13 C22 -169.1(2)
Eu1 N12 C13 C22 15.2(4)
N12 C13 C14 C15 -2.3(4)
C22 C13 C14 C15 167.3(3)
N12 N11 C15 C14 -0.4(3)
B1 N11 C15 C14 -169.8(3)
C13 C14 C15 N11 1.6(3)
O21 Eu1 N21 C26 23.1(2)
O22 Eu1 N21 C26 93.8(2)
N52 Eu1 N21 C26 165.5(2)
N32 Eu1 N21 C26 -123.9(2)
N12 Eu1 N21 C26 179.1(3)
O12 Eu1 N21 C26 -75.8(3)
N41 Eu1 N21 C26 -63.1(2)
N61 Eu1 N21 C26 78.8(2)
O11 Eu1 N21 C26 -11.7(3)
N1 Eu1 N21 C26 -33.1(3)
C72 Eu1 N21 C26 42.7(2)
O21 Eu1 N21 C22 -128.0(2)
O22 Eu1 N21 C22 -57.28(19)
N52 Eu1 N21 C22 14.5(2)
N32 Eu1 N21 C22 85.07(19)
N12 Eu1 N21 C22 28.01(18)
O12 Eu1 N21 C22 133.15(19)
N41 Eu1 N21 C22 145.8(2)
N61 Eu1 N21 C22 -72.3(2)
O11 Eu1 N21 C22 -162.77(17)
N1 Eu1 N21 C22 175.88(16)
C72 Eu1 N21 C22 -108.4(2)
C26 N21 C22 C23 -2.4(4)
Eu1 N21 C22 C23 150.7(2)
C26 N21 C22 C13 174.0(3)
Eu1 N21 C22 C13 -32.9(3)
N12 C13 C22 N21 15.0(4)
C14 C13 C22 N21 -154.0(3)
N12 C13 C22 C23 -168.6(3)
C14 C13 C22 C23 22.4(5)
N21 C22 C23 C24 1.7(5)
C13 C22 C23 C24 -174.4(3)
C22 C23 C24 C25 0.3(5)
C23 C24 C25 C26 -1.4(5)
C22 N21 C26 C25 1.2(4)
Eu1 N21 C26 C25 -149.0(2)
C24 C25 C26 N21 0.7(5)
N51 B1 N31 C35 136.7(3)
N11 B1 N31 C35 -106.5(3)
N51 B1 N31 N32 -62.2(3)
N11 B1 N31 N32 54.6(3)
C35 N31 N32 C33 0.4(3)
B1 N31 N32 C33 -164.0(3)
C35 N31 N32 Eu1 176.05(19)
B1 N31 N32 Eu1 11.6(4)
O21 Eu1 N32 C33 14.5(3)
O22 Eu1 N32 C33 128.3(2)
N52 Eu1 N32 C33 -160.4(2)
N12 Eu1 N32 C33 124.4(2)
O12 Eu1 N32 C33 -86.4(2)
N41 Eu1 N32 C33 -1.1(2)
N61 Eu1 N32 C33 -128.1(2)
O11 Eu1 N32 C33 -55.2(2)
N21 Eu1 N32 C33 71.5(2)
N1 Eu1 N32 C33 -71.4(2)
C72 Eu1 N32 C33 48.0(3)
O21 Eu1 N32 N31 -160.42(19)
O22 Eu1 N32 N31 -46.6(3)
N52 Eu1 N32 N31 24.6(2)
N12 Eu1 N32 N31 -50.6(2)
O12 Eu1 N32 N31 98.7(2)
N41 Eu1 N32 N31 -176.1(3)
N61 Eu1 N32 N31 57.0(3)
O11 Eu1 N32 N31 129.9(2)
N21 Eu1 N32 N31 -103.5(2)
N1 Eu1 N32 N31 113.6(2)
C72 Eu1 N32 N31 -127.0(2)
N31 N32 C33 C34 -0.4(3)
Eu1 N32 C33 C34 -176.36(18)
N31 N32 C33 C42 176.8(2)
Eu1 N32 C33 C42 0.8(4)
N32 C33 C34 C35 0.3(3)
C42 C33 C34 C35 -176.4(3)
N32 N31 C35 C34 -0.3(3)
B1 N31 C35 C34 162.4(3)
C33 C34 C35 N31 0.0(3)
O21 Eu1 N41 C46 10.0(2)
O22 Eu1 N41 C46 49.0(3)
N52 Eu1 N41 C46 -152.7(2)
N32 Eu1 N41 C46 -179.5(2)
N12 Eu1 N41 C46 131.5(2)
O12 Eu1 N41 C46 -105.7(2)
N61 Eu1 N41 C46 -62.8(2)
O11 Eu1 N41 C46 -55.6(2)
N21 Eu1 N41 C46 80.4(2)
N1 Eu1 N41 C46 -81.1(2)
C72 Eu1 N41 C46 23.1(2)
O21 Eu1 N41 C42 -169.2(2)
O22 Eu1 N41 C42 -130.2(2)
N52 Eu1 N41 C42 28.1(3)
N32 Eu1 N41 C42 1.3(2)
N12 Eu1 N41 C42 -47.7(2)
O12 Eu1 N41 C42 75.1(2)
N61 Eu1 N41 C42 118.0(2)
O11 Eu1 N41 C42 125.2(2)
N21 Eu1 N41 C42 -98.8(2)
N1 Eu1 N41 C42 99.7(2)
C72 Eu1 N41 C42 -156.0(2)
C46 N41 C42 C43 -0.8(4)
Eu1 N41 C42 C43 178.4(2)
C46 N41 C42 C33 179.4(3)
Eu1 N41 C42 C33 -1.4(3)
N32 C33 C42 N41 0.4(4)
C34 C33 C42 N41 176.9(3)
N32 C33 C42 C43 -179.4(3)
C34 C33 C42 C43 -2.9(5)
N41 C42 C43 C44 0.4(5)
C33 C42 C43 C44 -179.8(3)
C42 C43 C44 C45 0.5(5)
C43 C44 C45 C46 -0.9(5)
C42 N41 C46 C45 0.4(4)
Eu1 N41 C46 C45 -178.9(2)
C44 C45 C46 N41 0.5(5)
N31 B1 N51 C55 -127.7(3)
N11 B1 N51 C55 116.1(3)
N31 B1 N51 N52 60.2(3)
N11 B1 N51 N52 -56.0(3)
C55 N51 N52 C53 0.4(3)
B1 N51 N52 C53 173.9(2)
C55 N51 N52 Eu1 178.87(18)
B1 N51 N52 Eu1 -7.6(4)
O21 Eu1 N52 C53 -23.4(3)
O22 Eu1 N52 C53 -68.0(2)
N32 Eu1 N52 C53 151.4(2)
N12 Eu1 N52 C53 -141.2(2)
O12 Eu1 N52 C53 77.5(2)
N41 Eu1 N52 C53 126.8(2)
N61 Eu1 N52 C53 0.1(2)
O11 Eu1 N52 C53 48.7(2)
N21 Eu1 N52 C53 -128.9(2)
N1 Eu1 N52 C53 62.2(2)
C72 Eu1 N52 C53 -47.6(3)
O21 Eu1 N52 N51 158.33(19)
O22 Eu1 N52 N51 113.7(2)
N32 Eu1 N52 N51 -26.8(2)
N12 Eu1 N52 N51 40.6(2)
O12 Eu1 N52 N51 -100.8(2)
N41 Eu1 N52 N51 -51.4(3)
N61 Eu1 N52 N51 -178.2(2)
O11 Eu1 N52 N51 -129.6(2)
N21 Eu1 N52 N51 52.8(2)
N1 Eu1 N52 N51 -116.1(2)
C72 Eu1 N52 N51 134.1(2)
N51 N52 C53 C54 -0.5(3)
Eu1 N52 C53 C54 -179.11(18)
N51 N52 C53 C62 179.8(2)
Eu1 N52 C53 C62 1.2(4)
N52 C53 C54 C55 0.4(3)
C62 C53 C54 C55 -180.0(3)
N52 N51 C55 C54 -0.1(3)
B1 N51 C55 C54 -172.9(3)
C53 C54 C55 N51 -0.2(3)
O21 Eu1 N61 C66 -11.7(2)
O22 Eu1 N61 C66 -77.1(2)
N52 Eu1 N61 C66 -178.0(2)
N32 Eu1 N61 C66 146.5(2)
N12 Eu1 N61 C66 -135.9(2)
O12 Eu1 N61 C66 104.9(2)
N41 Eu1 N61 C66 60.0(2)
O11 Eu1 N61 C66 52.7(2)
N21 Eu1 N61 C66 -62.5(2)
N1 Eu1 N61 C66 79.3(2)
C72 Eu1 N61 C66 -31.5(2)
O21 Eu1 N61 C62 164.7(2)
O22 Eu1 N61 C62 99.3(2)
N52 Eu1 N61 C62 -1.57(19)
N32 Eu1 N61 C62 -37.0(2)
N12 Eu1 N61 C62 40.6(2)
O12 Eu1 N61 C62 -78.6(2)
N41 Eu1 N61 C62 -123.5(2)
O11 Eu1 N61 C62 -130.8(2)
N21 Eu1 N61 C62 113.9(2)
N1 Eu1 N61 C62 -104.3(2)
C72 Eu1 N61 C62 145.0(2)
C66 N61 C62 C63 -0.7(4)
Eu1 N61 C62 C63 -177.3(2)
C66 N61 C62 C53 179.3(2)
Eu1 N61 C62 C53 2.7(3)
N52 C53 C62 N61 -2.6(4)
C54 C53 C62 N61 177.8(3)
N52 C53 C62 C63 177.4(3)
C54 C53 C62 C63 -2.1(5)
N61 C62 C63 C64 0.0(4)
C53 C62 C63 C64 180.0(3)
C62 C63 C64 C65 0.9(4)
C63 C64 C65 C66 -1.1(4)
C62 N61 C66 C65 0.5(4)
Eu1 N61 C66 C65 177.0(2)
C64 C65 C66 N61 0.4(5)
O22 Eu1 O21 C72 -13.4(2)
N52 Eu1 O21 C72 -64.3(2)
N32 Eu1 O21 C72 123.9(2)
N12 Eu1 O21 C72 35.9(2)
O12 Eu1 O21 C72 -150.5(2)
N41 Eu1 O21 C72 137.9(2)
N61 Eu1 O21 C72 -85.0(2)
O11 Eu1 O21 C72 -151.5(2)
N21 Eu1 O21 C72 60.1(2)
N1 Eu1 O21 C72 -150.0(2)
O21 Eu1 O22 C71 12.18(19)
N52 Eu1 O22 C71 164.9(2)
N32 Eu1 O22 C71 -129.9(2)
N12 Eu1 O22 C71 -126.3(2)
O12 Eu1 O22 C71 107.7(2)
N41 Eu1 O22 C71 -31.2(2)
N61 Eu1 O22 C71 104.7(2)
O11 Eu1 O22 C71 53.8(2)
N21 Eu1 O22 C71 -64.5(2)
N1 Eu1 O22 C71 76.3(2)
C72 Eu1 O22 C71 5.95(19)
Eu1 O22 C71 C77 170.0(2)
Eu1 O22 C71 C72 -10.4(3)
O21 Eu1 C71 O22 -164.5(2)
N52 Eu1 C71 O22 -16.0(2)
N32 Eu1 C71 O22 73.4(2)
N12 Eu1 C71 O22 51.1(2)
O12 Eu1 C71 O22 -97.8(2)
N41 Eu1 C71 O22 155.91(19)
N61 Eu1 C71 O22 -69.8(2)
O11 Eu1 C71 O22 -131.6(2)
N21 Eu1 C71 O22 106.1(2)
N1 Eu1 C71 O22 -117.7(2)
C72 Eu1 C71 O22 -170.3(3)
O21 Eu1 C71 C77 172.0(6)
O22 Eu1 C71 C77 -23.5(5)
N52 Eu1 C71 C77 -39.5(6)
N32 Eu1 C71 C77 49.8(6)
N12 Eu1 C71 C77 27.5(6)
O12 Eu1 C71 C77 -121.4(5)
N41 Eu1 C71 C77 132.4(5)
N61 Eu1 C71 C77 -93.4(6)
O11 Eu1 C71 C77 -155.1(5)
N21 Eu1 C71 C77 82.6(5)
N1 Eu1 C71 C77 -141.2(5)
C72 Eu1 C71 C77 166.2(6)
O21 Eu1 C71 C72 5.81(14)
O22 Eu1 C71 C72 170.3(3)
N52 Eu1 C71 C72 154.31(16)
N32 Eu1 C71 C72 -116.31(18)
N12 Eu1 C71 C72 -138.63(17)
O12 Eu1 C71 C72 72.5(2)
N41 Eu1 C71 C72 -33.79(18)
N61 Eu1 C71 C72 100.47(17)
O11 Eu1 C71 C72 38.75(17)
N21 Eu1 C71 C72 -83.61(17)
N1 Eu1 C71 C72 52.60(18)
Eu1 O21 C72 C73 -164.3(2)
Eu1 O21 C72 C71 13.4(3)
O22 C71 C72 O21 -1.7(4)
C77 C71 C72 O21 177.8(3)
Eu1 C71 C72 O21 -8.5(2)
O22 C71 C72 C73 175.8(3)
C77 C71 C72 C73 -4.6(5)
Eu1 C71 C72 C73 169.0(3)
O22 C71 C72 Eu1 6.9(2)
C77 C71 C72 Eu1 -173.6(3)
O22 Eu1 C72 O21 163.0(2)
N52 Eu1 C72 O21 134.0(2)
N32 Eu1 C72 O21 -84.1(2)
N12 Eu1 C72 O21 -149.1(2)
O12 Eu1 C72 O21 35.9(2)
N41 Eu1 C72 O21 -41.8(2)
N61 Eu1 C72 O21 92.7(2)
O11 Eu1 C72 O21 25.7(2)
N21 Eu1 C72 O21 -111.4(2)
N1 Eu1 C72 O21 31.2(2)
O21 Eu1 C72 C73 33.4(4)
O22 Eu1 C72 C73 -163.5(5)
N52 Eu1 C72 C73 167.4(5)
N32 Eu1 C72 C73 -50.7(5)
N12 Eu1 C72 C73 -115.6(5)
O12 Eu1 C72 C73 69.4(5)
N41 Eu1 C72 C73 -8.4(5)
N61 Eu1 C72 C73 126.1(5)
O11 Eu1 C72 C73 59.2(5)
N21 Eu1 C72 C73 -78.0(5)
N1 Eu1 C72 C73 64.7(5)
O21 Eu1 C72 C71 -167.6(3)
O22 Eu1 C72 C71 -4.57(14)
N52 Eu1 C72 C71 -33.6(2)
N32 Eu1 C72 C71 108.3(2)
N12 Eu1 C72 C71 43.34(17)
O12 Eu1 C72 C71 -131.64(16)
N41 Eu1 C72 C71 150.57(16)
N61 Eu1 C72 C71 -74.88(16)
O11 Eu1 C72 C71 -141.88(17)
N21 Eu1 C72 C71 80.99(17)
N1 Eu1 C72 C71 -136.35(16)
O21 C72 C73 C74 177.6(3)
C71 C72 C73 C74 0.1(6)
Eu1 C72 C73 C74 154.4(4)
C72 C73 C74 C75 2.8(7)
C73 C74 C75 C76 -0.3(7)
C74 C75 C76 C77 -2.5(7)
C75 C76 C77 C71 0.0(6)
O22 C71 C77 C76 -175.9(3)
C72 C71 C77 C76 4.6(5)
Eu1 C71 C77 C76 -158.8(4)
O21 Eu1 O11 N1 176.22(17)
O22 Eu1 O11 N1 134.39(15)
N52 Eu1 O11 N1 34.77(17)
N32 Eu1 O11 N1 -43.02(17)
N12 Eu1 O11 N1 -45.6(5)
O12 Eu1 O11 N1 -2.48(14)
N41 Eu1 O11 N1 -93.29(16)
N61 Eu1 O11 N1 81.18(16)
N21 Eu1 O11 N1 -147.55(15)
C72 Eu1 O11 N1 166.89(16)
O21 Eu1 O12 N1 1.22(18)
O22 Eu1 O12 N1 -76.24(19)
N52 Eu1 O12 N1 -139.92(17)
N32 Eu1 O12 N1 140.96(18)
N12 Eu1 O12 N1 174.72(15)
N41 Eu1 O12 N1 75.88(16)
N61 Eu1 O12 N1 -73.18(16)
O11 Eu1 O12 N1 2.48(14)
N21 Eu1 O12 N1 88.5(2)
C72 Eu1 O12 N1 -11.1(2)
Eu1 O11 N1 O13 -176.3(2)
Eu1 O11 N1 O12 4.3(2)
Eu1 O12 N1 O13 176.2(2)
Eu1 O12 N1 O11 -4.4(3)
O21 Eu1 N1 O13 113(3)
O22 Eu1 N1 O13 58(3)
N52 Eu1 N1 O13 -31(3)
N32 Eu1 N1 O13 -105(3)
N12 Eu1 N1 O13 -77(3)
O12 Eu1 N1 O13 -68(3)
N41 Eu1 N1 O13 -166(3)
N61 Eu1 N1 O13 28(3)
O11 Eu1 N1 O13 116(3)
N21 Eu1 N1 O13 164(3)
C72 Eu1 N1 O13 103(3)
O21 Eu1 N1 O11 -3.41(16)
O22 Eu1 N1 O11 -57.99(18)
N52 Eu1 N1 O11 -147.35(16)
N32 Eu1 N1 O11 139.27(16)
N12 Eu1 N1 O11 167.11(15)
O12 Eu1 N1 O11 175.5(3)
N41 Eu1 N1 O11 78.09(16)
N61 Eu1 N1 O11 -87.71(16)
N21 Eu1 N1 O11 47.4(2)
C72 Eu1 N1 O11 -13.46(17)
O21 Eu1 N1 O12 -178.88(16)
O22 Eu1 N1 O12 126.55(16)
N52 Eu1 N1 O12 37.18(16)
N32 Eu1 N1 O12 -36.20(16)
N12 Eu1 N1 O12 -8.4(2)
N41 Eu1 N1 O12 -97.38(17)
N61 Eu1 N1 O12 96.82(17)
O11 Eu1 N1 O12 -175.5(3)
N21 Eu1 N1 O12 -128.04(16)
C72 Eu1 N1 O12 171.07(16)
