# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_14
_database_code_depnum_ccdc_archive 'CCDC 2027427'
loop_
_audit_author_name
_audit_author_address
'Bing Liu'
;SUST
China
;
_audit_update_record             
;
2020-11-15 deposited with the CCDC.	2020-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 Cl Eu O6'
_chemical_formula_sum            'C14 H10 Cl Eu O6'
_chemical_formula_weight         461.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -8.9294 11.1857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   15.35720(10)
_cell_length_b                   11.16410(10)
_cell_length_c                   8.40850(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.7260(10)
_cell_angle_gamma                90
_cell_volume                     1428.54(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    179.99(10)
_cell_measurement_reflns_used    9007
_cell_measurement_theta_min      2.8820
_cell_measurement_theta_max      75.8720

_exptl_crystal_description       hexagonal
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.146
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    33.413
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.66533
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.40.19a (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      179.99(10)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11560
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.904
_diffrn_reflns_theta_max         75.990
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2864
_reflns_number_gt                2763
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrysAlisPro 1.171.40.19a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.19a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.19a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           
'CrysAlisPro convention (1999,Acta A55,543-557)'
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0285P)²+1.8413P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00120(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2864
_refine_ls_number_parameters     208
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0185
_refine_ls_wR_factor_ref         0.0476
_refine_ls_wR_factor_gt          0.0465
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.005
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.38832(2) 0.84651(2) 0.03609(2) 0.00535(7) Uani 1 1 d . . . . .
Cl1 Cl 0.40647(4) 0.87004(5) -0.29344(7) 0.01188(12) Uani 1 1 d . . . . .
O1 O 0.11788(12) 1.44308(17) 0.1695(3) 0.0241(4) Uani 1 1 d . U . . .
O11 O 0.46860(11) 1.21959(15) -0.0062(2) 0.0123(3) Uani 1 1 d . . . . .
O12 O 0.39628(11) 1.04939(16) 0.0156(2) 0.0148(4) Uani 1 1 d . . . . .
O21 O -0.27272(11) 1.37933(16) 0.3168(2) 0.0139(4) Uani 1 1 d . . . . .
O22 O -0.27746(11) 1.26546(18) 0.0992(2) 0.0191(4) Uani 1 1 d . . . . .
C11 C 0.32242(15) 1.2333(2) 0.0503(3) 0.0097(5) Uani 1 1 d . . . . .
C12 C 0.31889(16) 1.3563(2) 0.0225(3) 0.0120(5) Uani 1 1 d . . . . .
H12A H 0.3642 1.3937 -0.0214 0.014 Uiso 1 1 calc R U . . .
C13 C 0.24869(16) 1.4232(2) 0.0597(3) 0.0154(5) Uani 1 1 d . . . . .
H13A H 0.2466 1.5054 0.0411 0.018 Uiso 1 1 calc R U . . .
C14 C 0.18121(17) 1.3666(2) 0.1250(4) 0.0165(5) Uani 1 1 d . . . . .
C15 C 0.18332(17) 1.2444(2) 0.1542(4) 0.0208(6) Uani 1 1 d . . . . .
H15A H 0.1380 1.2074 0.1986 0.025 Uiso 1 1 calc R U . . .
C16 C 0.25388(17) 1.1782(2) 0.1161(3) 0.0165(5) Uani 1 1 d . . . . .
H16A H 0.2556 1.0960 0.1346 0.020 Uiso 1 1 calc R U . . .
C17 C 0.40014(17) 1.1623(2) 0.0169(3) 0.0100(5) Uani 1 1 d . . . . .
C21 C -0.14275(16) 1.3575(2) 0.1966(3) 0.0090(5) Uani 1 1 d . . . . .
C22 C -0.09690(15) 1.4408(2) 0.2992(3) 0.0111(5) Uani 1 1 d . . . . .
H22A H -0.1250 1.4798 0.3757 0.013 Uiso 1 1 calc R U . . .
C23 C -0.00964(16) 1.4660(2) 0.2877(3) 0.0154(5) Uani 1 1 d . . . . .
H23A H 0.0204 1.5225 0.3555 0.018 Uiso 1 1 calc R U . . .
C24 C 0.03288(16) 1.4069(2) 0.1753(3) 0.0151(5) Uani 1 1 d . U . . .
C25 C -0.01195(18) 1.3237(3) 0.0714(3) 0.0190(6) Uani 1 1 d . . . . .
H25A H 0.0165 1.2845 -0.0046 0.023 Uiso 1 1 calc R U . . .
C26 C -0.09944(16) 1.3001(2) 0.0825(3) 0.0159(5) Uani 1 1 d . . . . .
H26A H -0.1298 1.2450 0.0128 0.019 Uiso 1 1 calc R U . . .
C27 C -0.23785(16) 1.3320(2) 0.2050(3) 0.0106(5) Uani 1 1 d . . . . .
O1W O 0.47040(12) 0.90534(15) 0.2906(2) 0.0144(4) Uani 1 1 d D . . . .
H1WB H 0.5046(19) 0.9760(17) 0.297(4) 0.033(10) Uiso 1 1 d D . . . .
H1WA H 0.501(2) 0.845(2) 0.355(5) 0.055(14) Uiso 1 1 d D . . . .


_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 O12 2.2760(18) . ?
Eu1 O22 2.2878(17) 3_575 ?
Eu1 O21 2.3251(16) 2_545 ?
Eu1 O11 2.3631(16) 3_675 ?
Eu1 O1W 2.4239(17) . ?
Eu1 Cl1 2.8053(6) 4_576 ?
Eu1 Cl1 2.8341(6) . ?
Cl1 Eu1 2.8053(6) 4_575 ?
O1 C24 1.374(3) . ?
O1 C14 1.383(3) . ?
O11 C17 1.268(3) . ?
O11 Eu1 2.3631(16) 3_675 ?
O12 C17 1.262(3) . ?
O21 C27 1.259(3) . ?
O21 Eu1 2.3252(16) 2 ?
O22 C27 1.252(3) . ?
O22 Eu1 2.2878(17) 3_575 ?
C11 C12 1.393(3) . ?
C11 C16 1.396(3) . ?
C11 C17 1.490(3) . ?
C12 C13 1.382(3) . ?
C13 C14 1.389(4) . ?
C14 C15 1.386(4) . ?
C15 C16 1.384(4) . ?
C21 C22 1.393(3) . ?
C21 C26 1.395(3) . ?
C21 C27 1.499(3) . ?
C22 C23 1.385(3) . ?
C23 C24 1.386(4) . ?
C24 C25 1.392(4) . ?
C25 C26 1.385(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
O12 Eu1 O22 123.37(7) . 3_575 ?
O12 Eu1 O21 86.33(6) . 2_545 ?
O22 Eu1 O21 77.30(6) 3_575 2_545 ?
O12 Eu1 O11 104.04(6) . 3_675 ?
O22 Eu1 O11 114.64(6) 3_575 3_675 ?
O21 Eu1 O11 153.27(6) 2_545 3_675 ?
O12 Eu1 O1W 76.72(6) . . ?
O22 Eu1 O1W 148.31(6) 3_575 . ?
O21 Eu1 O1W 80.28(6) 2_545 . ?
O11 Eu1 O1W 78.34(6) 3_675 . ?
O12 Eu1 Cl1 153.33(5) . 4_576 ?
O22 Eu1 Cl1 78.42(5) 3_575 4_576 ?
O21 Eu1 Cl1 83.95(5) 2_545 4_576 ?
O11 Eu1 Cl1 75.83(4) 3_675 4_576 ?
O1W Eu1 Cl1 77.18(4) . 4_576 ?
O12 Eu1 Cl1 79.66(5) . . ?
O22 Eu1 Cl1 74.28(5) 3_575 . ?
O21 Eu1 Cl1 133.47(5) 2_545 . ?
O11 Eu1 Cl1 73.14(4) 3_675 . ?
O1W Eu1 Cl1 136.91(4) . . ?
Cl1 Eu1 Cl1 124.288(13) 4_576 . ?
Eu1 Cl1 Eu1 113.802(18) 4_575 . ?
C24 O1 C14 122.3(2) . . ?
C17 O11 Eu1 131.36(15) . 3_675 ?
C17 O12 Eu1 175.10(17) . . ?
C27 O21 Eu1 139.70(16) . 2 ?
C27 O22 Eu1 159.28(17) . 3_575 ?
C12 C11 C16 119.1(2) . . ?
C12 C11 C17 120.4(2) . . ?
C16 C11 C17 120.4(2) . . ?
C13 C12 C11 120.6(2) . . ?
C12 C13 C14 119.3(2) . . ?
O1 C14 C15 124.1(2) . . ?
O1 C14 C13 114.5(2) . . ?
C15 C14 C13 121.2(2) . . ?
C16 C15 C14 119.0(2) . . ?
C15 C16 C11 120.8(2) . . ?
O12 C17 O11 122.8(2) . . ?
O12 C17 C11 119.7(2) . . ?
O11 C17 C11 117.5(2) . . ?
C22 C21 C26 119.0(2) . . ?
C22 C21 C27 120.8(2) . . ?
C26 C21 C27 120.2(2) . . ?
C23 C22 C21 120.4(2) . . ?
C22 C23 C24 120.0(2) . . ?
O1 C24 C23 114.9(2) . . ?
O1 C24 C25 124.5(2) . . ?
C23 C24 C25 120.5(2) . . ?
C26 C25 C24 119.1(2) . . ?
C25 C26 C21 121.0(2) . . ?
O22 C27 O21 124.4(2) . . ?
O22 C27 C21 117.6(2) . . ?
O21 C27 C21 118.0(2) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C11 C12 C13 0.1(4) . . . . ?
C17 C11 C12 C13 -177.3(2) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C24 O1 C14 C15 -31.7(4) . . . . ?
C24 O1 C14 C13 153.7(3) . . . . ?
C12 C13 C14 O1 175.1(2) . . . . ?
C12 C13 C14 C15 0.3(4) . . . . ?
O1 C14 C15 C16 -174.7(3) . . . . ?
C13 C14 C15 C16 -0.4(5) . . . . ?
C14 C15 C16 C11 0.4(4) . . . . ?
C12 C11 C16 C15 -0.3(4) . . . . ?
C17 C11 C16 C15 177.1(3) . . . . ?
Eu1 O11 C17 O12 -5.9(4) 3_675 . . . ?
Eu1 O11 C17 C11 172.74(15) 3_675 . . . ?
C12 C11 C17 O12 -167.7(2) . . . . ?
C16 C11 C17 O12 15.0(4) . . . . ?
C12 C11 C17 O11 13.6(3) . . . . ?
C16 C11 C17 O11 -163.7(2) . . . . ?
C26 C21 C22 C23 0.0(4) . . . . ?
C27 C21 C22 C23 -178.4(2) . . . . ?
C21 C22 C23 C24 -0.9(4) . . . . ?
C14 O1 C24 C23 150.3(3) . . . . ?
C14 O1 C24 C25 -34.0(4) . . . . ?
C22 C23 C24 O1 177.0(2) . . . . ?
C22 C23 C24 C25 1.2(4) . . . . ?
O1 C24 C25 C26 -175.9(3) . . . . ?
C23 C24 C25 C26 -0.5(4) . . . . ?
C24 C25 C26 C21 -0.5(4) . . . . ?
C22 C21 C26 C25 0.7(4) . . . . ?
C27 C21 C26 C25 179.1(2) . . . . ?
Eu1 O22 C27 O21 -5.7(7) 3_575 . . . ?
Eu1 O22 C27 C21 174.9(4) 3_575 . . . ?
Eu1 O21 C27 O22 26.2(4) 2 . . . ?
Eu1 O21 C27 C21 -154.45(18) 2 . . . ?
C22 C21 C27 O22 172.9(2) . . . . ?
C26 C21 C27 O22 -5.4(3) . . . . ?
C22 C21 C27 O21 -6.5(3) . . . . ?
C26 C21 C27 O21 175.1(2) . . . . ?

_refine_diff_density_max         0.949
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.098

