# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1856728'
_audit_update_record             
;
2018-11-19 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H6 Eu O8'
_chemical_formula_weight         358.07

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'
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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0361(3)
_cell_length_b                   8.7341(5)
_cell_length_c                   9.4880(5)
_cell_angle_alpha                64.7590(10)
_cell_angle_beta                 77.761(2)
_cell_angle_gamma                85.895(2)
_cell_volume                     442.06(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2760
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      32.84

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.690
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             338
_exptl_absorpt_coefficient_mu    7.118
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3302
_exptl_absorpt_correction_T_max  0.4580
_exptl_absorpt_process_details   'Higashi (1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 'Bruker SMART CCD area'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            5880
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         32.84
_reflns_number_total             2760
_reflns_number_gt                2622
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0212P)²+1.1814P] where P=(Fo²+2Fc²)/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         2760
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0215
_refine_ls_wR_factor_ref         0.0541
_refine_ls_wR_factor_gt          0.0528
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_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 0.93957(2) 0.246363(17) 0.339472(15) 0.01120(5) Uani 1 1 d . . .
O1 O 0.8361(4) -0.0020(3) 0.6228(3) 0.0175(4) Uani 1 1 d . . .
O2 O 0.6397(4) 0.2299(3) 0.5679(3) 0.0211(5) Uani 1 1 d . . .
O3 O 0.3396(4) -0.0786(3) 0.6835(3) 0.0229(5) Uani 1 1 d . . .
O4 O 0.0845(4) -0.2115(3) 0.9029(3) 0.0233(5) Uani 1 1 d . . .
O5 O 0.8759(5) 0.5412(3) 0.3292(3) 0.0281(5) Uani 1 1 d . . .
O6 O 0.6909(5) 0.4705(3) 0.1892(3) 0.0283(5) Uani 1 1 d . . .
O7 O 1.1913(4) 0.2782(4) 0.4893(3) 0.0264(5) Uani 1 1 d . . .
O8 O 1.2626(4) 0.3977(4) 0.1435(3) 0.0304(6) Uani 1 1 d . . .
C1 C 0.6886(4) 0.0885(4) 0.6661(3) 0.0125(5) Uani 1 1 d . . .
C2 C 0.5883(5) 0.0366(4) 0.8401(3) 0.0133(5) Uani 1 1 d . . .
C3 C 0.3866(4) -0.0588(4) 0.9180(3) 0.0125(5) Uani 1 1 d . . .
C4 C 0.2617(5) -0.1208(4) 0.8308(3) 0.0146(5) Uani 1 1 d . . .
C5 C 0.7003(4) 0.0954(3) 0.9219(3) 0.0144(5) Uani 1 1 d . . .
H5 H 0.8336 0.1595 0.8698 0.022 Uiso 1 1 calc R . .
C6 C 0.7382(4) 0.5740(3) 0.2395(3) 0.0332(9) Uani 1 1 d R . .
H8A H 1.3531 0.4588 0.1497 0.040 Uiso 1 1 d R . .
H7B H 1.1894 0.3324 0.5445 0.040 Uiso 1 1 d R . .
H7A H 1.2768 0.1963 0.5308 0.040 Uiso 1 1 d R . .
H8B H 1.2724 0.4522 0.0461 0.040 Uiso 1 1 d R . .
H6 H 0.6798 0.6903 0.1987 0.040 Uiso 1 1 d R . .

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 0.01200(7) 0.01374(8) 0.00881(7) -0.00557(5) -0.00198(4) -0.00062(5)
O1 0.0194(10) 0.0210(11) 0.0124(9) -0.0093(8) -0.0006(7) 0.0060(8)
O2 0.0240(11) 0.0219(11) 0.0123(9) -0.0049(9) -0.0005(8) 0.0064(9)
O3 0.0258(11) 0.0342(13) 0.0105(9) -0.0109(9) -0.0002(8) -0.0114(10)
O4 0.0227(11) 0.0340(13) 0.0151(10) -0.0128(10) 0.0021(8) -0.0133(10)
O5 0.0359(14) 0.0234(12) 0.0321(14) -0.0151(11) -0.0155(11) 0.0042(10)
O6 0.0365(14) 0.0262(13) 0.0299(13) -0.0147(11) -0.0191(11) 0.0087(11)
O7 0.0269(12) 0.0317(14) 0.0317(13) -0.0187(11) -0.0189(10) 0.0074(10)
O8 0.0244(12) 0.0451(16) 0.0151(10) -0.0056(11) -0.0003(9) -0.0168(11)
C1 0.0119(10) 0.0174(13) 0.0089(10) -0.0068(10) -0.0006(8) -0.0007(9)
C2 0.0128(11) 0.0185(13) 0.0096(11) -0.0074(10) -0.0014(9) 0.0010(9)
C3 0.0132(11) 0.0182(13) 0.0080(10) -0.0074(10) -0.0018(9) -0.0002(9)
C4 0.0158(12) 0.0198(13) 0.0110(11) -0.0086(11) -0.0040(9) 0.0001(10)
C5 0.0124(11) 0.0218(14) 0.0094(11) -0.0075(10) 0.0005(9) -0.0037(10)
C6 0.047(2) 0.0242(18) 0.039(2) -0.0183(17) -0.0242(18) 0.0150(16)

_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 O1 2.378(2) 2_756 ?
Eu1 O7 2.392(2) . ?
Eu1 O8 2.396(2) . ?
Eu1 O3 2.412(2) 2_656 ?
Eu1 O2 2.471(2) . ?
Eu1 O4 2.479(2) 2_656 ?
Eu1 O6 2.495(3) . ?
Eu1 O5 2.539(3) . ?
Eu1 O1 2.614(2) . ?
Eu1 C4 2.797(3) 2_656 ?
Eu1 Eu1 4.2005(3) 2_756 ?
O1 C1 1.268(4) . ?
O1 Eu1 2.378(2) 2_756 ?
O2 C1 1.251(4) . ?
O3 C4 1.271(3) . ?
O3 Eu1 2.412(2) 2_656 ?
O4 C4 1.260(4) . ?
O4 Eu1 2.479(2) 2_656 ?
O5 C6 1.247(3) . ?
O6 C6 1.260(4) . ?
O7 H7B 0.8406 . ?
O7 H7A 0.8522 . ?
O8 H8A 0.8172 . ?
O8 H8B 0.8308 . ?
C1 C2 1.508(4) . ?
C2 C5 1.391(4) . ?
C2 C3 1.400(4) . ?
C3 C5 1.399(3) 2_657 ?
C3 C4 1.501(4) . ?
C4 Eu1 2.797(3) 2_656 ?
C5 C3 1.399(3) 2_657 ?
C5 H5 0.9300 . ?
C6 H6 0.9883 . ?

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
O1 Eu1 O7 79.47(9) 2_756 . ?
O1 Eu1 O8 85.04(10) 2_756 . ?
O7 Eu1 O8 75.45(9) . . ?
O1 Eu1 O3 83.33(9) 2_756 2_656 ?
O7 Eu1 O3 149.37(9) . 2_656 ?
O8 Eu1 O3 128.14(8) . 2_656 ?
O1 Eu1 O2 116.43(7) 2_756 . ?
O7 Eu1 O2 84.54(9) . . ?
O8 Eu1 O2 147.54(10) . . ?
O3 Eu1 O2 80.70(8) 2_656 . ?
O1 Eu1 O4 80.27(8) 2_756 2_656 ?
O7 Eu1 O4 144.92(9) . 2_656 ?
O8 Eu1 O4 74.53(8) . 2_656 ?
O3 Eu1 O4 53.72(7) 2_656 2_656 ?
O2 Eu1 O4 130.30(8) . 2_656 ?
O1 Eu1 O6 151.79(8) 2_756 . ?
O7 Eu1 O6 125.60(9) . . ?
O8 Eu1 O6 89.14(10) . . ?
O3 Eu1 O6 78.69(9) 2_656 . ?
O2 Eu1 O6 81.98(9) . . ?
O4 Eu1 O6 71.58(9) 2_656 . ?
O1 Eu1 O5 151.70(8) 2_756 . ?
O7 Eu1 O5 74.05(9) . . ?
O8 Eu1 O5 78.89(11) . . ?
O3 Eu1 O5 124.86(9) 2_656 . ?
O2 Eu1 O5 71.10(9) . . ?
O4 Eu1 O5 116.86(9) 2_656 . ?
O6 Eu1 O5 51.70(9) . . ?
O1 Eu1 O1 65.50(8) 2_756 . ?
O7 Eu1 O1 74.20(9) . . ?
O8 Eu1 O1 140.78(9) . . ?
O3 Eu1 O1 75.64(8) 2_656 . ?
O2 Eu1 O1 50.95(7) . . ?
O4 Eu1 O1 121.59(8) 2_656 . ?
O6 Eu1 O1 128.97(9) . . ?
O5 Eu1 O1 115.21(8) . . ?
O1 Eu1 C4 81.85(8) 2_756 2_656 ?
O7 Eu1 C4 161.24(9) . 2_656 ?
O8 Eu1 C4 101.31(9) . 2_656 ?
O3 Eu1 C4 26.98(8) 2_656 2_656 ?
O2 Eu1 C4 105.48(8) . 2_656 ?
O4 Eu1 C4 26.78(8) 2_656 2_656 ?
O6 Eu1 C4 72.26(9) . 2_656 ?
O5 Eu1 C4 123.94(9) . 2_656 ?
O1 Eu1 C4 99.51(8) . 2_656 ?
O1 Eu1 Eu1 34.49(5) 2_756 2_756 ?
O7 Eu1 Eu1 74.16(7) . 2_756 ?
O8 Eu1 Eu1 115.67(8) . 2_756 ?
O3 Eu1 Eu1 77.29(6) 2_656 2_756 ?
O2 Eu1 Eu1 81.95(5) . 2_756 ?
O4 Eu1 Eu1 103.31(7) 2_656 2_756 ?
O6 Eu1 Eu1 152.90(7) . 2_756 ?
O5 Eu1 Eu1 139.78(6) . 2_756 ?
O1 Eu1 Eu1 31.01(5) . 2_756 ?
C4 Eu1 Eu1 91.29(6) 2_656 2_756 ?
C1 O1 Eu1 155.13(19) . 2_756 ?
C1 O1 Eu1 90.23(17) . . ?
Eu1 O1 Eu1 114.50(8) 2_756 . ?
C1 O2 Eu1 97.42(18) . . ?
C4 O3 Eu1 93.64(18) . 2_656 ?
C4 O4 Eu1 90.79(17) . 2_656 ?
C6 O5 Eu1 92.15(18) . . ?
C6 O6 Eu1 93.91(17) . . ?
Eu1 O7 H7B 135.2 . . ?
Eu1 O7 H7A 118.5 . . ?
H7B O7 H7A 101.6 . . ?
Eu1 O8 H8A 128.0 . . ?
Eu1 O8 H8B 128.2 . . ?
H8A O8 H8B 94.4 . . ?
O2 C1 O1 120.9(3) . . ?
O2 C1 C2 118.4(3) . . ?
O1 C1 C2 120.4(3) . . ?
C5 C2 C3 119.9(2) . . ?
C5 C2 C1 116.7(2) . . ?
C3 C2 C1 123.3(2) . . ?
C5 C3 C2 119.8(2) 2_657 . ?
C5 C3 C4 119.7(2) 2_657 . ?
C2 C3 C4 120.6(2) . . ?
O4 C4 O3 121.7(3) . . ?
O4 C4 C3 120.3(3) . . ?
O3 C4 C3 118.1(3) . . ?
O4 C4 Eu1 62.43(16) . 2_656 ?
O3 C4 Eu1 59.38(15) . 2_656 ?
C3 C4 Eu1 175.6(2) . 2_656 ?
C2 C5 C3 120.3(2) . 2_657 ?
C2 C5 H5 119.8 . . ?
C3 C5 H5 119.8 2_657 . ?
O5 C6 O6 122.2(3) . . ?
O5 C6 H6 117.1 . . ?
O6 C6 H6 120.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O8 H8B O6 0.83 2.00 2.818(4) 166.4 2_765
O7 H7A O2 0.85 2.35 2.913(3) 124.1 1_655
O7 H7A O3 0.85 2.27 3.051(4) 152.9 1_655
O7 H7B O5 0.84 1.92 2.747(4) 169.0 2_766
O8 H8A O6 0.82 2.17 2.867(4) 143.8 1_655

_diffrn_measured_fraction_theta_max 0.838
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         1.659
_refine_diff_density_min         -1.608
_refine_diff_density_rms         0.164
