# 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_14
_database_code_depnum_ccdc_archive 'CCDC 1828712'
_audit_update_record             
;
2018-03-09 deposited with the CCDC.
2018-06-01 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         'C12 H8 Cl Eu O5'
_chemical_formula_sum            'C12 H8 Cl Eu O5'
_chemical_formula_weight         419.59

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'
O O 0.0106 0.0060 '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'
Eu Eu -0.1578 3.6682 '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                   13.1597(9)
_cell_length_b                   12.8654(9)
_cell_length_c                   7.1664(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.323(2)
_cell_angle_gamma                90
_cell_volume                     1193.67(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    27611
_cell_measurement_theta_min      3.031
_cell_measurement_theta_max      27.491

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.335
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   0.4262
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    5.490
_shelx_estimated_absorpt_T_min   0.347
_shelx_estimated_absorpt_T_max   0.760?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Sphere (CrystalClear)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_number         ?
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27535
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.421
_diffrn_reflns_theta_max         25.013
_diffrn_reflns_theta_full        25.013
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2080
_reflns_number_gt                2029
_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       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_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           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0149P)²+7.6824P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2080
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0217
_refine_ls_wR_factor_ref         0.0509
_refine_ls_wR_factor_gt          0.0504
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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_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 0.91582(2) 0.62305(2) 0.20153(2) 0.00858(8) Uani 1 1 d . . . . .
Cl1 Cl 1.01295(7) 0.71400(7) -0.08037(13) 0.01439(19) Uani 1 1 d . . . . .
O11 O 0.8551(2) 0.5202(2) -0.0506(4) 0.0182(6) Uani 1 1 d . . . . .
O12 O 0.9117(2) 0.4318(2) -0.2767(4) 0.0133(6) Uani 1 1 d . . . . .
C11 C 0.7337(3) 0.4203(4) -0.2619(6) 0.0191(9) Uani 1 1 d . . . . .
C12 C 0.7212(3) 0.3258(4) -0.3729(6) 0.0225(9) Uani 1 1 d . . . . .
H12 H 0.7802 0.2913 -0.4022 0.027 Uiso 1 1 calc R U . . .
C13 C 0.6257(3) 0.2863(4) -0.4353(6) 0.0237(9) Uani 1 1 d . . . . .
H13 H 0.6180 0.2235 -0.5060 0.028 Uiso 1 1 calc R U . . .
C14 C 0.5384(4) 0.3382(3) -0.3956(6) 0.0204(9) Uani 1 1 d . . . . .
C15 C 0.5466(3) 0.4311(3) -0.2897(6) 0.0182(9) Uani 1 1 d . . . . .
C16 C 0.6501(3) 0.4694(4) -0.2205(6) 0.0206(9) Uani 1 1 d . . . . .
H16 H 0.6591 0.5303 -0.1444 0.025 Uiso 1 1 calc R U . . .
C17 C 0.8404(3) 0.4611(3) -0.1916(5) 0.0097(7) Uani 1 1 d . . . . .
O21 O 0.2282(2) 0.2261(2) -0.5779(4) 0.0167(6) Uani 1 1 d . . . . .
O22 O 0.1720(2) 0.3672(2) -0.4502(4) 0.0164(6) Uani 1 1 d . . . . .
C21 C 0.3515(3) 0.3497(4) -0.4241(6) 0.0195(9) Uani 1 1 d . . . . .
C22 C 0.3639(3) 0.4456(4) -0.3178(6) 0.0233(9) Uani 1 1 d . . . . .
H22 H 0.3048 0.4819 -0.2936 0.028 Uiso 1 1 calc R U . . .
C23 C 0.4601(3) 0.4842(4) -0.2519(6) 0.0226(9) Uani 1 1 d . . . . .
H23 H 0.4682 0.5469 -0.1807 0.027 Uiso 1 1 calc R U . . .
C24 C 0.4352(3) 0.2983(4) -0.4620(6) 0.0217(9) Uani 1 1 d . . . . .
H24 H 0.4263 0.2355 -0.5328 0.026 Uiso 1 1 calc R U . . .
C25 C 0.2437(3) 0.3106(3) -0.4890(5) 0.0126(8) Uani 1 1 d . . . . .
O1W O 0.8995(2) 0.4531(2) 0.3327(4) 0.0188(6) Uani 1 1 d . . . . .
H1WA H 0.9296 0.4077 0.2710 0.028 Uiso 1 1 d R U . . .
H1WB H 0.8348 0.4347 0.3118 0.028 Uiso 1 1 d R U . . .


_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 O11 2.267(3) . ?
Eu1 O22 2.295(3) 3_665 ?
Eu1 O12 2.345(3) 3_765 ?
Eu1 O21 2.352(3) 2_654 ?
Eu1 O1W 2.405(3) . ?
Eu1 Cl1 2.7848(9) 4_576 ?
Eu1 Cl1 2.8301(9) . ?
Cl1 Eu1 2.7849(9) 4_575 ?
O11 C17 1.251(5) . ?
O12 C17 1.265(5) . ?
O12 Eu1 2.345(3) 3_765 ?
C11 C16 1.348(6) . ?
C11 C12 1.445(6) . ?
C11 C17 1.499(5) . ?
C12 C13 1.354(6) . ?
C13 C14 1.402(6) . ?
C14 C15 1.410(6) . ?
C14 C24 1.449(6) . ?
C15 C23 1.396(6) . ?
C15 C16 1.449(6) . ?
O21 C25 1.258(5) . ?
O21 Eu1 2.352(3) 2_644 ?
O22 C25 1.261(5) . ?
O22 Eu1 2.295(3) 3_665 ?
C21 C24 1.353(6) . ?
C21 C22 1.444(6) . ?
C21 C25 1.499(5) . ?
C22 C23 1.363(6) . ?

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
O11 Eu1 O22 119.74(10) . 3_665 ?
O11 Eu1 O12 101.29(10) . 3_765 ?
O22 Eu1 O12 116.06(10) 3_665 3_765 ?
O11 Eu1 O21 83.30(10) . 2_654 ?
O22 Eu1 O21 77.16(10) 3_665 2_654 ?
O12 Eu1 O21 159.63(9) 3_765 2_654 ?
O11 Eu1 O1W 74.76(10) . . ?
O22 Eu1 O1W 69.71(10) 3_665 . ?
O12 Eu1 O1W 77.70(10) 3_765 . ?
O21 Eu1 O1W 122.49(10) 2_654 . ?
O11 Eu1 Cl1 161.42(8) . 4_576 ?
O22 Eu1 Cl1 76.55(7) 3_665 4_576 ?
O12 Eu1 Cl1 76.70(7) 3_765 4_576 ?
O21 Eu1 Cl1 92.59(7) 2_654 4_576 ?
O1W Eu1 Cl1 121.95(7) . 4_576 ?
O11 Eu1 Cl1 79.19(8) . . ?
O22 Eu1 Cl1 152.44(7) 3_665 . ?
O12 Eu1 Cl1 75.30(7) 3_765 . ?
O21 Eu1 Cl1 86.25(7) 2_654 . ?
O1W Eu1 Cl1 137.60(7) . . ?
Cl1 Eu1 Cl1 82.463(18) 4_576 . ?
Eu1 Cl1 Eu1 119.43(3) 4_575 . ?
C17 O11 Eu1 168.4(3) . . ?
C17 O12 Eu1 138.6(2) . 3_765 ?
C16 C11 C12 119.9(4) . . ?
C16 C11 C17 120.9(4) . . ?
C12 C11 C17 119.2(4) . . ?
C13 C12 C11 120.4(4) . . ?
C12 C13 C14 120.0(4) . . ?
C13 C14 C15 121.7(4) . . ?
C13 C14 C24 121.3(4) . . ?
C15 C14 C24 117.0(4) . . ?
C23 C15 C14 122.2(4) . . ?
C23 C15 C16 121.1(4) . . ?
C14 C15 C16 116.7(4) . . ?
C11 C16 C15 121.3(4) . . ?
O11 C17 O12 123.3(3) . . ?
O11 C17 C11 119.0(3) . . ?
O12 C17 C11 117.7(3) . . ?
C25 O21 Eu1 136.4(2) . 2_644 ?
C25 O22 Eu1 134.7(2) . 3_665 ?
C24 C21 C22 120.3(4) . . ?
C24 C21 C25 122.2(4) . . ?
C22 C21 C25 117.5(4) . . ?
C23 C22 C21 120.3(4) . . ?
C22 C23 C15 119.6(4) . . ?
C21 C24 C14 120.7(4) . . ?
O21 C25 O22 123.4(3) . . ?
O21 C25 C21 120.3(4) . . ?
O22 C25 C21 116.2(4) . . ?

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(6) . . . . ?
C17 C11 C12 C13 178.9(4) . . . . ?
C11 C12 C13 C14 1.3(7) . . . . ?
C12 C13 C14 C15 -0.6(7) . . . . ?
C12 C13 C14 C24 179.4(4) . . . . ?
C13 C14 C15 C23 179.0(4) . . . . ?
C24 C14 C15 C23 -1.1(6) . . . . ?
C13 C14 C15 C16 -1.2(6) . . . . ?
C24 C14 C15 C16 178.8(4) . . . . ?
C12 C11 C16 C15 -1.8(6) . . . . ?
C17 C11 C16 C15 179.3(4) . . . . ?
C23 C15 C16 C11 -177.7(4) . . . . ?
C14 C15 C16 C11 2.4(6) . . . . ?
Eu1 O11 C17 O12 -6.8(15) . . . . ?
Eu1 O11 C17 C11 171.6(11) . . . . ?
Eu1 O12 C17 O11 40.8(6) 3_765 . . . ?
Eu1 O12 C17 C11 -137.6(3) 3_765 . . . ?
C16 C11 C17 O11 21.7(6) . . . . ?
C12 C11 C17 O11 -157.2(4) . . . . ?
C16 C11 C17 O12 -159.9(4) . . . . ?
C12 C11 C17 O12 21.2(5) . . . . ?
C24 C21 C22 C23 -1.1(7) . . . . ?
C25 C21 C22 C23 178.8(4) . . . . ?
C21 C22 C23 C15 0.7(7) . . . . ?
C14 C15 C23 C22 0.4(7) . . . . ?
C16 C15 C23 C22 -179.5(4) . . . . ?
C22 C21 C24 C14 0.4(6) . . . . ?
C25 C21 C24 C14 -179.5(4) . . . . ?
C13 C14 C24 C21 -179.4(4) . . . . ?
C15 C14 C24 C21 0.7(6) . . . . ?
Eu1 O21 C25 O22 -3.6(6) 2_644 . . . ?
Eu1 O21 C25 C21 176.9(3) 2_644 . . . ?
Eu1 O22 C25 O21 89.5(5) 3_665 . . . ?
Eu1 O22 C25 C21 -91.0(4) 3_665 . . . ?
C24 C21 C25 O21 1.8(6) . . . . ?
C22 C21 C25 O21 -178.1(4) . . . . ?
C24 C21 C25 O22 -177.7(4) . . . . ?
C22 C21 C25 O22 2.3(5) . . . . ?

_refine_diff_density_max         1.357
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.117

