# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_exp_466
#TrackingRef 'exp_466.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H40 Eu2 O19'
_chemical_formula_weight         1080.60

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'
Eu Eu -0.1578 3.6682 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pnna

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z'
'x, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'-x, y-1/2, z-1/2'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.4385(14)
_cell_length_b                   27.184(2)
_cell_length_c                   9.3482(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2652.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1985
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      22.4

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1068
_exptl_absorpt_coefficient_mu    2.402
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7297
_exptl_absorpt_correction_T_max  0.7615
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8916
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2346
_reflns_number_gt                1502
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2008)'
_computing_publication_material  SHELXTL

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1039P)^2^+35.1540P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2346
_refine_ls_number_parameters     146
_refine_ls_number_restraints     47
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0774
_refine_ls_wR_factor_ref         0.2317
_refine_ls_wR_factor_gt          0.2045
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

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 0.7500 0.0000 0.02597(9) 0.0380(4) Uani 1 2 d SU . .
C1 C 0.5003(14) 0.0781(5) 0.0756(18) 0.050(3) Uani 1 1 d U . .
C2 C 0.4720(14) 0.1303(4) 0.1242(14) 0.044(3) Uani 1 1 d U A .
C3 C 0.5719(16) 0.1634(5) 0.156(2) 0.078(6) Uani 1 1 d . . .
H3 H 0.6569 0.1543 0.1428 0.093 Uiso 1 1 calc R A .
C4 C 0.3470(15) 0.1456(4) 0.1413(16) 0.053(4) Uani 1 1 d . . .
H4 H 0.2804 0.1242 0.1188 0.064 Uiso 1 1 calc R A .
C5 C 0.3190(14) 0.1928(4) 0.1920(16) 0.050(3) Uani 1 1 d . A .
H5 H 0.2346 0.2028 0.2047 0.060 Uiso 1 1 calc R . .
C6 C 0.4208(14) 0.2246(4) 0.2232(16) 0.052(4) Uani 1 1 d . . .
C7 C 0.5415(14) 0.2093(5) 0.208(2) 0.068(5) Uani 1 1 d . A .
C8 C 0.639(3) 0.2500 0.2500 0.079(7) Uani 1 2 d SU . .
C9 C 0.714(3) 0.2647(10) 0.118(3) 0.135(10) Uani 1 1 d U A .
H9A H 0.7525 0.2359 0.0761 0.202 Uiso 1 1 d R . .
H9B H 0.7800 0.2875 0.1446 0.202 Uiso 1 1 d R . .
H9C H 0.6582 0.2799 0.0491 0.202 Uiso 1 1 d R . .
O1 O 0.6132(12) 0.0669(3) 0.0664(14) 0.075(3) Uani 1 1 d U A .
O2 O 0.4125(10) 0.0518(3) 0.0452(14) 0.073(4) Uani 1 1 d . . .
O3W O 0.8070(12) -0.0269(4) -0.2329(16) 0.180(10) Uani 1 1 d D A .
H3WA H 0.8343 -0.0560 -0.2458 0.216 Uiso 1 1 d R . .
H3WB H 0.8379 -0.0054 -0.2890 0.216 Uiso 1 1 d R . .
O6W O 0.535(7) 0.265(3) 0.856(8) 0.16(3) Uani 0.25 1 d PU . .
H6WA H 0.5444 0.2964 0.8481 0.190 Uiso 0.25 1 d PR . .
H6WB H 0.5172 0.2535 0.9373 0.190 Uiso 0.25 1 d PR . .
O4W O 0.8530(16) 0.0361(6) 0.2350(17) 0.122(5) Uani 0.50 1 d P A 1
H4WA H 0.9164 0.0552 0.2217 0.146 Uiso 0.50 1 d PR A 1
H4WB H 0.8549 0.0194 0.3118 0.146 Uiso 0.50 1 d PR A 1
O4 O 0.8530(16) 0.0361(6) 0.2350(17) 0.122(5) Uani 0.50 1 d PDU A 2
C10 C 0.926(3) 0.0540(12) 0.327(4) 0.105(10) Uani 0.50 1 d PDU A 2
H10 H 0.9900 0.0323 0.3558 0.127 Uiso 0.50 1 calc PR A 2
O5 O 0.933(3) 0.0949(12) 0.388(3) 0.139(14) Uani 0.50 1 d PD A 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Eu1 0.0489(6) 0.0149(5) 0.0502(6) 0.000 0.000 0.0010(4)
C1 0.058(8) 0.020(6) 0.073(9) -0.016(6) -0.004(8) -0.004(5)
C2 0.054(9) 0.018(6) 0.061(8) -0.016(5) -0.006(7) -0.003(5)
C3 0.049(10) 0.034(8) 0.150(17) -0.049(9) 0.003(10) 0.000(7)
C4 0.057(10) 0.030(6) 0.073(9) -0.016(6) -0.009(8) -0.004(6)
C5 0.043(9) 0.026(6) 0.080(10) -0.014(6) -0.002(8) -0.001(6)
C6 0.060(10) 0.025(6) 0.070(9) -0.026(6) 0.003(8) -0.004(6)
C7 0.040(8) 0.026(7) 0.138(15) -0.042(8) -0.006(9) 0.007(6)
C8 0.084(11) 0.061(9) 0.093(11) -0.021(8) 0.000 0.000
C9 0.137(13) 0.116(12) 0.151(13) -0.031(9) 0.012(9) -0.015(9)
O1 0.067(6) 0.036(5) 0.122(7) -0.035(5) -0.003(6) 0.004(4)
O2 0.047(7) 0.029(5) 0.144(11) -0.042(6) 0.005(7) 0.001(5)
O3W 0.26(2) 0.123(13) 0.155(15) -0.104(11) 0.137(17) -0.096(15)
O6W 0.16(3) 0.16(3) 0.16(3) 0.008(10) 0.002(10) 0.001(10)
O4W 0.125(6) 0.126(6) 0.114(6) -0.018(5) -0.015(4) -0.017(5)
O4 0.125(6) 0.126(6) 0.114(6) -0.018(5) -0.015(4) -0.017(5)
C10 0.100(13) 0.119(14) 0.098(12) -0.008(9) -0.011(9) -0.015(10)
O5 0.10(2) 0.22(4) 0.10(2) -0.07(2) 0.015(18) -0.09(2)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 O2 2.304(10) 5_655 ?
Eu1 O2 2.304(10) 6_655 ?
Eu1 O1 2.343(10) 2_655 ?
Eu1 O1 2.343(10) . ?
Eu1 O4W 2.436(15) . ?
Eu1 O4 2.436(15) 2_655 ?
Eu1 O4W 2.436(15) 2_655 ?
Eu1 O3W 2.597(14) . ?
Eu1 O3W 2.597(14) 2_655 ?
C1 O2 1.196(16) . ?
C1 O1 1.220(16) . ?
C1 C2 1.518(16) . ?
C2 C4 1.379(19) . ?
C2 C3 1.409(19) . ?
C3 C7 1.374(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(16) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.34(2) . ?
C6 C6 1.47(2) 3 ?
C7 C8 1.55(2) . ?
C8 C9 1.52(3) 3 ?
C8 C9 1.52(3) . ?
C8 C7 1.55(2) 3 ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
O2 Eu1 2.304(10) 5_655 ?
O3W H3WA 0.8499 . ?
O3W H3WB 0.8500 . ?
O6W H6WA 0.8500 . ?
O6W H6WB 0.8499 . ?
O4W H4WA 0.8500 . ?
O4W H4WB 0.8500 . ?
C10 O5 1.251(5) . ?
C10 H4WA 0.9868 . ?
C10 H4WB 1.2106 . ?
C10 H10 0.9300 . ?

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
O2 Eu1 O2 146.4(6) 5_655 6_655 ?
O2 Eu1 O1 91.2(4) 5_655 2_655 ?
O2 Eu1 O1 94.1(4) 6_655 2_655 ?
O2 Eu1 O1 94.1(4) 5_655 . ?
O2 Eu1 O1 91.2(4) 6_655 . ?
O1 Eu1 O1 161.4(6) 2_655 . ?
O2 Eu1 O4W 143.4(5) 5_655 . ?
O2 Eu1 O4W 70.1(5) 6_655 . ?
O1 Eu1 O4W 85.1(5) 2_655 . ?
O1 Eu1 O4W 80.0(5) . . ?
O2 Eu1 O4 70.1(5) 5_655 2_655 ?
O2 Eu1 O4 143.4(5) 6_655 2_655 ?
O1 Eu1 O4 80.0(5) 2_655 2_655 ?
O1 Eu1 O4 85.1(5) . 2_655 ?
O4W Eu1 O4 73.4(8) . 2_655 ?
O2 Eu1 O4W 70.1(5) 5_655 2_655 ?
O2 Eu1 O4W 143.4(5) 6_655 2_655 ?
O1 Eu1 O4W 80.0(5) 2_655 2_655 ?
O1 Eu1 O4W 85.1(5) . 2_655 ?
O4W Eu1 O4W 73.4(8) . 2_655 ?
O4 Eu1 O4W 0.0(10) 2_655 2_655 ?
O2 Eu1 O3W 74.2(4) 5_655 . ?
O2 Eu1 O3W 74.6(5) 6_655 . ?
O1 Eu1 O3W 78.0(4) 2_655 . ?
O1 Eu1 O3W 120.6(4) . . ?
O4W Eu1 O3W 139.4(5) . . ?
O4 Eu1 O3W 137.3(5) 2_655 . ?
O4W Eu1 O3W 137.3(5) 2_655 . ?
O2 Eu1 O3W 74.6(5) 5_655 2_655 ?
O2 Eu1 O3W 74.2(4) 6_655 2_655 ?
O1 Eu1 O3W 120.6(4) 2_655 2_655 ?
O1 Eu1 O3W 78.0(4) . 2_655 ?
O4W Eu1 O3W 137.3(5) . 2_655 ?
O4 Eu1 O3W 139.4(5) 2_655 2_655 ?
O4W Eu1 O3W 139.4(5) 2_655 2_655 ?
O3W Eu1 O3W 42.6(3) . 2_655 ?
O2 C1 O1 125.0(12) . . ?
O2 C1 C2 118.7(13) . . ?
O1 C1 C2 116.3(12) . . ?
C4 C2 C3 118.9(11) . . ?
C4 C2 C1 120.0(12) . . ?
C3 C2 C1 121.1(13) . . ?
C7 C3 C2 118.9(14) . . ?
C7 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C2 C4 C5 120.9(13) . . ?
C2 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 118.6(13) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C7 C6 C5 120.0(11) . . ?
C7 C6 C6 109.3(7) . 3 ?
C5 C6 C6 130.7(8) . 3 ?
C6 C7 C3 122.7(14) . . ?
C6 C7 C8 111.5(12) . . ?
C3 C7 C8 125.9(15) . . ?
C9 C8 C9 118(3) 3 . ?
C9 C8 C7 111.0(13) 3 . ?
C9 C8 C7 108.5(12) . . ?
C9 C8 C7 108.5(12) 3 3 ?
C9 C8 C7 111.0(13) . 3 ?
C7 C8 C7 98.4(19) . 3 ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.9 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 O1 Eu1 142.6(9) . . ?
C1 O2 Eu1 176.5(11) . 5_655 ?
Eu1 O3W H3WA 118.1 . . ?
Eu1 O3W H3WB 117.9 . . ?
H3WA O3W H3WB 115.2 . . ?
H6WA O6W H6WB 118.6 . . ?
Eu1 O4W H4WA 118.2 . . ?
Eu1 O4W H4WB 118.2 . . ?
H4WA O4W H4WB 115.5 . . ?
O5 C10 H4WA 115.6 . . ?
O5 C10 H4WB 141.2 . . ?
H4WA C10 H4WB 81.0 . . ?
O5 C10 H10 113.0 . . ?
H4WA C10 H10 112.8 . . ?
H4WB C10 H10 88.7 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.421
_refine_diff_density_min         -0.849
_refine_diff_density_rms         0.219


_database_code_depnum_ccdc_archive 'CCDC 918148'