# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_hggfkkhk_sq
_database_code_depnum_ccdc_archive 'CCDC 1473242'
_audit_update_record             
;
2016-04-10 deposited with the CCDC.
2018-10-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        zju-41
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H6 Eu2 N3 O18'
_chemical_formula_weight         892.21

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.132(2)
_cell_length_b                   13.2260(8)
_cell_length_c                   15.1630(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.288(5)
_cell_angle_gamma                90
_cell_volume                     4974.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    200
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      18.3

_exptl_crystal_description       NO
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_F_000             1692
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.548
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24610
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.642
_diffrn_reflns_theta_max         26.277
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             4920
_reflns_number_gt                4312
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.1940P)²+334.2346P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4920
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1143
_refine_ls_R_factor_gt           0.1069
_refine_ls_wR_factor_ref         0.3246
_refine_ls_wR_factor_gt          0.3163
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_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 0.32375(3) 0.31655(5) 0.52929(5) 0.0295(3) Uani 1 1 d . . . . .
O1 O 0.3604(7) 0.4792(12) 0.5749(12) 0.080(5) Uani 1 1 d . . . . .
O3 O 0.2218(5) 0.3246(8) 0.4281(8) 0.044(3) Uani 1 1 d . . . . .
O6 O 0.4040(8) 0.3429(13) 0.4497(15) 0.090(6) Uani 1 1 d . . . . .
O6U O 0.3676(9) 0.3059(13) 0.6849(12) 0.085(6) Uani 1 1 d . . . . .
O9 O 0.4097(6) 0.2101(17) 0.5406(13) 0.089(6) Uani 1 1 d . . . . .
O10 O 0.2896(4) 0.4244(9) 0.4046(8) 0.048(3) Uani 1 1 d . . . . .
O10B O 0.4678(7) 0.235(2) 0.4454(17) 0.118(8) Uani 1 1 d . . . . .
O11 O 0.1842(5) 0.7004(10) 0.0903(9) 0.051(3) Uani 1 1 d . . . . .
O16 O 0.2602(5) 0.6101(10) 0.1111(9) 0.055(3) Uani 1 1 d . . . . .
N6 N 0.4286(6) 0.263(2) 0.4858(17) 0.090(8) Uani 1 1 d . . . . .
C7 C 0.2254(5) 0.5081(11) 0.2545(10) 0.034(3) Uani 1 1 d . . . . .
H7 H 0.2624 0.5081 0.2547 0.041 Uiso 1 1 calc R U . . .
C7P C 0.2425(7) 0.3978(12) 0.3874(12) 0.045(4) Uani 1 1 d . . . . .
C8 C 0.2036(5) 0.4509(11) 0.3182(9) 0.033(3) Uani 1 1 d . . . . .
C9 C 0.2135(6) 0.6313(13) 0.1251(11) 0.041(3) Uani 1 1 d . . . . .
C14L C 0.0545(6) 0.5028(14) 0.2515(13) 0.047(4) Uani 1 1 d . . . . .
C17 C 0.1135(6) 0.5055(13) 0.2516(12) 0.045(4) Uani 1 1 d . . . . .
C19 C 0.1921(6) 0.5642(12) 0.1919(10) 0.039(3) Uani 1 1 d . . . . .
C20 C 0.1366(7) 0.5638(12) 0.1901(10) 0.043(4) Uani 1 1 d . . . . .
H20 H 0.1146 0.6025 0.1477 0.052 Uiso 1 1 calc R U . . .
C25 C 0.1477(5) 0.4504(11) 0.3138(10) 0.032(3) Uani 1 1 d . . . . .
H25 H 0.1329 0.4113 0.3547 0.038 Uiso 1 1 calc R U . . .
N30 N 0.0314(13) 0.496(3) 0.326(2) 0.031(8) Uani 0.5 1 d . . P . .
C30 C 0.041(3) 0.517(6) 0.333(8) 0.13(5) Uani 0.5 1 d . . P . .
C31 C 0.0199(7) 0.5011(15) 0.1720(17) 0.063(5) Uani 1 1 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 O3 2.335(11) 7_556 ?
Eu1 O11 2.360(12) 4_545 ?
Eu1 O16 2.382(12) 6_566 ?
Eu1 O1 2.398(14) . ?
Eu1 O10 2.413(12) . ?
Eu1 O6U 2.442(17) . ?
Eu1 O6 2.535(14) . ?
Eu1 O9 2.560(17) . ?
Eu1 O3 2.769(13) . ?
Eu1 N6 2.906(17) . ?
Eu1 C7P 2.921(17) . ?
Eu1 Eu1 4.0702(13) 7_556 ?
O3 C7P 1.300(19) . ?
O3 Eu1 2.335(11) 7_556 ?
O6 N6 1.30(3) . ?
O9 N6 1.24(3) . ?
O10 C7P 1.22(2) . ?
O10B N6 1.29(2) . ?
O11 C9 1.24(2) . ?
O11 Eu1 2.360(12) 4 ?
O16 C9 1.26(2) . ?
O16 Eu1 2.382(12) 6_565 ?
C7 C19 1.38(2) . ?
C7 C8 1.405(18) . ?
C7 H7 0.9300 . ?
C7P C8 1.49(2) . ?
C8 C25 1.396(19) . ?
C9 C19 1.51(2) . ?
C14L C30 1.36(11) . ?
C14L N30 1.36(4) . ?
C14L C31 1.37(3) . ?
C14L C17 1.48(2) . ?
C17 C25 1.38(2) . ?
C17 C20 1.41(2) . ?
C19 C20 1.39(2) . ?
C20 H20 0.9300 . ?
C25 H25 0.9300 . ?
N30 C31 1.30(4) 2 ?
C30 C31 1.53(8) 2 ?
C31 N30 1.30(4) 2 ?
C31 C30 1.53(8) 2 ?

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
O3 Eu1 O11 73.0(5) 7_556 4_545 ?
O3 Eu1 O16 77.4(4) 7_556 6_566 ?
O11 Eu1 O16 133.2(4) 4_545 6_566 ?
O3 Eu1 O1 145.1(5) 7_556 . ?
O11 Eu1 O1 141.8(6) 4_545 . ?
O16 Eu1 O1 75.1(5) 6_566 . ?
O3 Eu1 O10 124.2(4) 7_556 . ?
O11 Eu1 O10 78.9(5) 4_545 . ?
O16 Eu1 O10 89.1(5) 6_566 . ?
O1 Eu1 O10 76.5(5) . . ?
O3 Eu1 O6U 81.4(5) 7_556 . ?
O11 Eu1 O6U 132.4(5) 4_545 . ?
O16 Eu1 O6U 75.9(6) 6_566 . ?
O1 Eu1 O6U 71.4(6) . . ?
O10 Eu1 O6U 147.1(5) . . ?
O3 Eu1 O6 134.8(5) 7_556 . ?
O11 Eu1 O6 72.5(6) 4_545 . ?
O16 Eu1 O6 147.5(5) 6_566 . ?
O1 Eu1 O6 73.5(6) . . ?
O10 Eu1 O6 75.8(6) . . ?
O6U Eu1 O6 101.4(8) . . ?
O3 Eu1 O9 89.3(5) 7_556 . ?
O11 Eu1 O9 70.1(6) 4_545 . ?
O16 Eu1 O9 145.0(5) 6_566 . ?
O1 Eu1 O9 101.1(7) . . ?
O10 Eu1 O9 124.5(5) . . ?
O6U Eu1 O9 70.1(7) . . ?
O6 Eu1 O9 51.7(6) . . ?
O3 Eu1 O3 74.5(4) 7_556 . ?
O11 Eu1 O3 69.1(4) 4_545 . ?
O16 Eu1 O3 68.5(4) 6_566 . ?
O1 Eu1 O3 113.8(5) . . ?
O10 Eu1 O3 50.4(3) . . ?
O6U Eu1 O3 140.4(6) . . ?
O6 Eu1 O3 117.8(6) . . ?
O9 Eu1 O3 138.9(6) . . ?
O3 Eu1 N6 111.8(7) 7_556 . ?
O11 Eu1 N6 68.6(5) 4_545 . ?
O16 Eu1 N6 158.0(5) 6_566 . ?
O1 Eu1 N6 87.9(7) . . ?
O10 Eu1 N6 100.8(7) . . ?
O6U Eu1 N6 85.5(7) . . ?
O6 Eu1 N6 26.6(7) . . ?
O9 Eu1 N6 25.2(7) . . ?
O3 Eu1 N6 132.5(5) . . ?
O3 Eu1 C7P 100.5(4) 7_556 . ?
O11 Eu1 C7P 73.2(5) 4_545 . ?
O16 Eu1 C7P 77.6(5) 6_566 . ?
O1 Eu1 C7P 94.2(6) . . ?
O10 Eu1 C7P 24.2(4) . . ?
O6U Eu1 C7P 152.3(6) . . ?
O6 Eu1 C7P 96.6(6) . . ?
O9 Eu1 C7P 137.2(5) . . ?
O3 Eu1 C7P 26.2(4) . . ?
N6 Eu1 C7P 118.3(6) . . ?
O3 Eu1 Eu1 41.0(3) 7_556 7_556 ?
O11 Eu1 Eu1 65.8(3) 4_545 7_556 ?
O16 Eu1 Eu1 68.0(3) 6_566 7_556 ?
O1 Eu1 Eu1 138.2(5) . 7_556 ?
O10 Eu1 Eu1 83.6(3) . 7_556 ?
O6U Eu1 Eu1 116.0(5) . 7_556 ?
O6 Eu1 Eu1 136.2(5) . 7_556 ?
O9 Eu1 Eu1 120.4(5) . 7_556 ?
O3 Eu1 Eu1 33.6(2) . 7_556 ?
N6 Eu1 Eu1 132.2(4) . 7_556 ?
C7P Eu1 Eu1 59.6(3) . 7_556 ?
C7P O3 Eu1 167.9(12) . 7_556 ?
C7P O3 Eu1 83.5(10) . . ?
Eu1 O3 Eu1 105.5(4) 7_556 . ?
N6 O6 Eu1 92.8(13) . . ?
N6 O9 Eu1 93.2(13) . . ?
C7P O10 Eu1 101.9(10) . . ?
C9 O11 Eu1 141.2(11) . 4 ?
C9 O16 Eu1 136.1(11) . 6_565 ?
O9 N6 O10B 124(3) . . ?
O9 N6 O6 122.2(17) . . ?
O10B N6 O6 112(3) . . ?
O9 N6 Eu1 61.6(11) . . ?
O10B N6 Eu1 164.6(17) . . ?
O6 N6 Eu1 60.6(9) . . ?
C19 C7 C8 120.1(12) . . ?
C19 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
O10 C7P O3 124.2(16) . . ?
O10 C7P C8 121.1(14) . . ?
O3 C7P C8 114.7(15) . . ?
O10 C7P Eu1 53.9(9) . . ?
O3 C7P Eu1 70.3(9) . . ?
C8 C7P Eu1 173.4(12) . . ?
C25 C8 C7 118.1(12) . . ?
C25 C8 C7P 124.8(13) . . ?
C7 C8 C7P 117.0(12) . . ?
O11 C9 O16 126.8(15) . . ?
O11 C9 C19 118.0(14) . . ?
O16 C9 C19 115.2(14) . . ?
C30 C14L N30 15(4) . . ?
C30 C14L C31 126(4) . . ?
N30 C14L C31 116.0(19) . . ?
C30 C14L C17 114(4) . . ?
N30 C14L C17 124.2(19) . . ?
C31 C14L C17 119.7(17) . . ?
C25 C17 C20 117.8(14) . . ?
C25 C17 C14L 120.0(15) . . ?
C20 C17 C14L 122.2(15) . . ?
C7 C19 C20 120.6(13) . . ?
C7 C19 C9 122.4(13) . . ?
C20 C19 C9 117.0(14) . . ?
C19 C20 C17 120.6(13) . . ?
C19 C20 H20 119.7 . . ?
C17 C20 H20 119.7 . . ?
C17 C25 C8 122.8(13) . . ?
C17 C25 H25 118.6 . . ?
C8 C25 H25 118.6 . . ?
C31 N30 C14L 125(3) 2 . ?
C14L C30 C31 109(7) . 2 ?
N30 C31 C14L 119(2) 2 . ?
N30 C31 C30 12(4) 2 2 ?
C14L C31 C30 122(5) . 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
Eu1 O9 N6 O10B -163(2) . . . . ?
Eu1 O9 N6 O6 2(2) . . . . ?
Eu1 O6 N6 O9 -2(2) . . . . ?
Eu1 O6 N6 O10B 164.8(19) . . . . ?
Eu1 O10 C7P O3 -3(2) . . . . ?
Eu1 O10 C7P C8 174.8(13) . . . . ?
Eu1 O3 C7P O10 -136(5) 7_556 . . . ?
Eu1 O3 C7P O10 2.9(17) . . . . ?
Eu1 O3 C7P C8 46(6) 7_556 . . . ?
Eu1 O3 C7P C8 -175.4(14) . . . . ?
Eu1 O3 C7P Eu1 -138(5) 7_556 . . . ?
C19 C7 C8 C25 2(2) . . . . ?
C19 C7 C8 C7P -176.0(15) . . . . ?
O10 C7P C8 C25 -157.5(17) . . . . ?
O3 C7P C8 C25 21(2) . . . . ?
O10 C7P C8 C7 20(2) . . . . ?
O3 C7P C8 C7 -161.3(15) . . . . ?
Eu1 O11 C9 O16 14(3) 4 . . . ?
Eu1 O11 C9 C19 -166.2(13) 4 . . . ?
Eu1 O16 C9 O11 6(3) 6_565 . . . ?
Eu1 O16 C9 C19 -173.6(12) 6_565 . . . ?
C30 C14L C17 C25 48(5) . . . . ?
N30 C14L C17 C25 35(3) . . . . ?
C31 C14L C17 C25 -141.0(19) . . . . ?
C30 C14L C17 C20 -131(5) . . . . ?
N30 C14L C17 C20 -144(3) . . . . ?
C31 C14L C17 C20 40(3) . . . . ?
C8 C7 C19 C20 -1(2) . . . . ?
C8 C7 C19 C9 176.7(15) . . . . ?
O11 C9 C19 C7 -158.6(17) . . . . ?
O16 C9 C19 C7 21(2) . . . . ?
O11 C9 C19 C20 19(2) . . . . ?
O16 C9 C19 C20 -161.2(16) . . . . ?
C7 C19 C20 C17 -1(3) . . . . ?
C9 C19 C20 C17 -178.3(16) . . . . ?
C25 C17 C20 C19 1(3) . . . . ?
C14L C17 C20 C19 -179.7(16) . . . . ?
C20 C17 C25 C8 0(3) . . . . ?
C14L C17 C25 C8 -179.2(16) . . . . ?
C7 C8 C25 C17 -2(2) . . . . ?
C7P C8 C25 C17 176.1(16) . . . . ?
C30 C14L N30 C31 125(20) . . . 2 ?
C31 C14L N30 C31 -9(4) . . . 2 ?
C17 C14L N30 C31 175(3) . . . 2 ?
N30 C14L C30 C31 -37(14) . . . 2 ?
C31 C14L C30 C31 16(8) . . . 2 ?
C17 C14L C30 C31 -174(4) . . . 2 ?
C30 C14L C31 N30 -12(6) . . . 2 ?
N30 C14L C31 N30 2(3) . . . 2 ?
C17 C14L C31 N30 178(2) . . . 2 ?
C30 C14L C31 C30 1(3) . . . 2 ?
N30 C14L C31 C30 15(5) . . . 2 ?
C17 C14L C31 C30 -169(4) . . . 2 ?

_refine_diff_density_max         6.496
_refine_diff_density_min         -6.564
_refine_diff_density_rms         0.363

_shelxl_version_number           2013-2



