# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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 1957993'
loop_
_audit_author_name
_audit_author_address
'Zhan Shi'
; State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, College of Chemistry, Jilin 
China
;
_audit_update_record             
;
2019-10-08 deposited with the CCDC.	2019-11-17 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT213_2                   
; 
PROBLEM: Atom O3 has ADP max/min Ratio ..... 25.0 prolat
RESPONSE: This atom O3 has some disorder.
;
_vrf_PLAT602_2                   
; 
PROBLEM:  VERY LARGE Solvent Accessible VOID(S) in Structure ! Info 
RESPONSE: This alert is generated because the disorder molecule exist in the structure.
;
# end Validation Reply Form
_audit_creation_date             2019-10-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H24 Eu N3 O10'
_chemical_formula_sum            'C9 H2 Eu N O7'
_chemical_formula_weight         388.08
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x, z+3/4'
'-x, -y, z+1/2'
'y, -x, z+1/4'

_cell_length_a                   10.4323(4)
_cell_length_b                   10.4323(4)
_cell_length_c                   14.3109(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1557.50(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4776
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.045
_exptl_absorpt_correction_T_max  0.534
_exptl_absorpt_correction_T_min  0.365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12785
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.081
_diffrn_reflns_theta_min         2.416
_diffrn_ambient_temperature      299.11
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.920
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2557
_reflns_number_total             2927
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.733
_refine_diff_density_min         -1.007
_refine_diff_density_rms         0.175
_refine_ls_abs_structure_details 
;
 Flack x determined using 1025 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2927
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      0.979
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0877P)²+2.5761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1239
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.571(4)
 0.429(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(N1) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C3) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Rotating group:
 N1(H1a,H1b)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 -0.63667(2) -1.36474(2) -0.64125(11) 0.03027(4) Uani 1 1 d . . . . .
O1 O -0.5797(5) -1.1754(3) -0.5709(3) 0.0505(13) Uani 1 1 d . . . . .
O2 O -0.4632(5) -1.1724(4) -0.4429(3) 0.0717(16) Uani 1 1 d . . . . .
O3 O -0.4276(8) -0.7472(5) -0.2747(3) 0.102(2) Uani 1 1 d . . . . .
O4 O -0.3922(5) -0.5753(4) -0.3688(4) 0.089(2) Uani 1 1 d . . . . .
O5 O -0.5870(4) -0.5828(3) -0.6859(2) 0.0431(10) Uani 1 1 d . . . . .
O6 O -0.5983(7) -0.7581(7) -0.7548(4) 0.120(3) Uani 1 1 d . . . . .
O7 O -0.7905(6) -1.1873(7) -0.6570(8) 0.170(3) Uani 1 1 d . . . . .
N1 N -0.6099(9) -0.9609(7) -0.6698(5) 0.115(3) Uani 1 1 d . U . . .
H1A H -0.6745 -0.9148 -0.7212 0.138 Uiso 1 1 d GR . . . .
H1B H -0.6818 -1.0457 -0.6774 0.138 Uiso 1 1 d GR . . . .
C1 C -0.5199(7) -1.1173(4) -0.5114(6) 0.0485(18) Uani 1 1 d . . . . .
C2 C -0.5191(7) -0.9708(4) -0.5074(4) 0.0410(16) Uani 1 1 d . . . . .
C3 C -0.4787(6) -0.9048(6) -0.4318(4) 0.0528(16) Uani 1 1 d . U . . .
H3 H -0.4622 -0.9484 -0.3764 0.063 Uiso 1 1 calc R . . . .
C4 C -0.4604(6) -0.7651(6) -0.4358(5) 0.0495(16) Uani 1 1 d . U . . .
C5 C -0.5004(11) -0.7048(3) -0.5109(6) 0.0372(12) Uani 1 1 d . . . . .
H5 H -0.5067 -0.6159 -0.5089 0.045 Uiso 1 1 calc R . . . .
C6 C -0.5353(7) -0.7699(5) -0.5969(3) 0.0406(17) Uani 1 1 d . . . . .
C7 C -0.5544(5) -0.9057(5) -0.5924(3) 0.0362(13) Uani 1 1 d . U . . .
C8 C -0.4360(6) -0.6962(6) -0.3449(4) 0.0521(18) Uani 1 1 d . . . . .
C9 C -0.5862(6) -0.6903(6) -0.6750(4) 0.0414(16) 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 O1 2.296(4) . ?
Eu1 O2 2.360(5) 2_344 ?
Eu1 O3 2.337(5) 3_434 ?
Eu1 O4 2.253(4) 2_444 ?
Eu1 O5 2.419(4) 1_545 ?
Eu1 O5 3.034(4) 4_535 ?
Eu1 O6 2.359(6) 4_535 ?
Eu1 O7 2.460(6) . ?
Eu1 C8 3.077(6) 3_434 ?
Eu1 C9 3.186(5) 4_535 ?
O1 C1 1.217(8) . ?
O2 Eu1 2.360(5) 4_635 ?
O2 C1 1.281(9) . ?
O3 Eu1 2.337(5) 3_435 ?
O3 C8 1.139(8) . ?
O4 Eu1 2.253(4) 4_645 ?
O4 C8 1.385(8) . ?
O5 Eu1 3.034(4) 2_354 ?
O5 Eu1 2.419(4) 1_565 ?
O5 C9 1.133(7) . ?
O6 Eu1 2.359(6) 2_354 ?
O6 C9 1.350(8) . ?
N1 H1A 1.1073 . ?
N1 H1B 1.1647 . ?
N1 C7 1.376(9) . ?
C1 C2 1.529(6) . ?
C2 C3 1.349(9) . ?
C2 C7 1.441(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.471(9) . ?
C4 C5 1.314(11) . ?
C4 C8 1.508(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.452(10) . ?
C6 C7 1.432(7) . ?
C6 C9 1.490(7) . ?
C8 Eu1 3.077(6) 3_435 ?
C9 Eu1 3.186(5) 2_354 ?

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 O2 136.94(18) . 2_344 ?
O1 Eu1 O3 81.63(16) . 3_434 ?
O1 Eu1 O5 150.42(15) . 1_545 ?
O1 Eu1 O5 70.72(12) . 4_535 ?
O1 Eu1 O6 85.2(2) . 4_535 ?
O1 Eu1 O7 64.0(2) . . ?
O1 Eu1 C8 100.01(15) . 3_434 ?
O1 Eu1 C9 75.97(15) . 4_535 ?
O2 Eu1 O5 112.82(14) 2_344 4_535 ?
O2 Eu1 O5 71.85(16) 2_344 1_545 ?
O2 Eu1 O7 75.4(2) 2_344 . ?
O2 Eu1 C8 90.05(17) 2_344 3_434 ?
O2 Eu1 C9 94.95(16) 2_344 4_535 ?
O3 Eu1 O2 101.7(2) 3_434 2_344 ?
O3 Eu1 O5 101.09(17) 3_434 1_545 ?
O3 Eu1 O5 145.22(18) 3_434 4_535 ?
O3 Eu1 O6 155.8(2) 3_434 4_535 ?
O3 Eu1 O7 74.7(3) 3_434 . ?
O3 Eu1 C8 18.57(17) 3_434 3_434 ?
O3 Eu1 C9 157.60(17) 3_434 4_535 ?
O4 Eu1 O1 78.03(19) 2_444 . ?
O4 Eu1 O2 144.87(19) 2_444 2_344 ?
O4 Eu1 O3 84.2(2) 2_444 3_434 ?
O4 Eu1 O5 73.03(17) 2_444 1_545 ?
O4 Eu1 O5 70.07(16) 2_444 4_535 ?
O4 Eu1 O6 112.9(2) 2_444 4_535 ?
O4 Eu1 O7 138.5(2) 2_444 . ?
O4 Eu1 C8 85.38(19) 2_444 3_434 ?
O4 Eu1 C9 90.79(19) 2_444 4_535 ?
O5 Eu1 O5 93.46(11) 1_545 4_535 ?
O5 Eu1 O7 145.4(2) 1_545 . ?
O5 Eu1 C8 154.93(14) 4_535 3_434 ?
O5 Eu1 C8 83.77(15) 1_545 3_434 ?
O5 Eu1 C9 98.24(14) 1_545 4_535 ?
O5 Eu1 C9 20.80(13) 4_535 4_535 ?
O6 Eu1 O2 74.6(2) 4_535 2_344 ?
O6 Eu1 O5 100.38(19) 4_535 1_545 ?
O6 Eu1 O5 43.18(18) 4_535 4_535 ?
O6 Eu1 O7 81.3(3) 4_535 . ?
O6 Eu1 C8 161.7(2) 4_535 3_434 ?
O6 Eu1 C9 22.4(2) 4_535 4_535 ?
O7 Eu1 O5 109.5(3) . 4_535 ?
O7 Eu1 C8 85.3(3) . 3_434 ?
O7 Eu1 C9 95.5(3) . 4_535 ?
C8 Eu1 C9 174.97(17) 3_434 4_535 ?
C1 O1 Eu1 150.3(4) . . ?
C1 O2 Eu1 145.1(4) . 4_635 ?
C8 O3 Eu1 120.6(5) . 3_435 ?
C8 O4 Eu1 166.3(5) . 4_645 ?
Eu1 O5 Eu1 113.26(13) 1_565 2_354 ?
C9 O5 Eu1 153.7(4) . 1_565 ?
C9 O5 Eu1 87.2(3) . 2_354 ?
C9 O6 Eu1 115.8(5) . 2_354 ?
H1A N1 H1B 82.9 . . ?
C7 N1 H1A 127.4 . . ?
C7 N1 H1B 131.6 . . ?
O1 C1 O2 123.2(4) . . ?
O1 C1 C2 121.8(6) . . ?
O2 C1 C2 114.7(6) . . ?
C3 C2 C1 122.7(6) . . ?
C3 C2 C7 121.1(4) . . ?
C7 C2 C1 116.0(5) . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.0(6) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C8 117.4(5) . . ?
C5 C4 C3 117.7(6) . . ?
C5 C4 C8 122.1(5) . . ?
C4 C5 H5 118.3 . . ?
C4 C5 C6 123.4(4) . . ?
C6 C5 H5 118.3 . . ?
C5 C6 C9 117.7(5) . . ?
C7 C6 C5 117.3(4) . . ?
C7 C6 C9 122.4(5) . . ?
N1 C7 C2 126.1(5) . . ?
N1 C7 C6 115.9(5) . . ?
C6 C7 C2 117.9(4) . . ?
O3 C8 Eu1 40.8(4) . 3_435 ?
O3 C8 O4 128.2(6) . . ?
O3 C8 C4 123.4(6) . . ?
O4 C8 Eu1 88.0(4) . 3_435 ?
O4 C8 C4 106.0(5) . . ?
C4 C8 Eu1 163.2(4) . 3_435 ?
O5 C9 Eu1 72.0(3) . 2_354 ?
O5 C9 O6 113.7(5) . . ?
O5 C9 C6 131.1(5) . . ?
O6 C9 Eu1 41.8(3) . 2_354 ?
O6 C9 C6 112.1(5) . . ?
C6 C9 Eu1 152.1(4) . 2_354 ?

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 O1 C1 O2 -11.3(15) . . . . ?
Eu1 O1 C1 C2 175.3(6) . . . . ?
Eu1 O2 C1 O1 26.9(14) 4_635 . . . ?
Eu1 O2 C1 C2 -159.3(6) 4_635 . . . ?
Eu1 O3 C8 O4 12.0(11) 3_435 . . . ?
Eu1 O3 C8 C4 172.0(5) 3_435 . . . ?
Eu1 O4 C8 Eu1 -74.0(19) 4_645 . . 3_435 ?
Eu1 O4 C8 O3 -82(2) 4_645 . . . ?
Eu1 O4 C8 C4 115.4(18) 4_645 . . . ?
Eu1 O5 C9 Eu1 142.5(9) 1_565 . . 2_354 ?
Eu1 O5 C9 O6 3.5(5) 2_354 . . . ?
Eu1 O5 C9 O6 146.0(7) 1_565 . . . ?
Eu1 O5 C9 C6 161.7(7) 2_354 . . . ?
Eu1 O5 C9 C6 -55.8(13) 1_565 . . . ?
Eu1 O6 C9 O5 -5.0(8) 2_354 . . . ?
Eu1 O6 C9 C6 -167.4(4) 2_354 . . . ?
O1 C1 C2 C3 164.7(7) . . . . ?
O1 C1 C2 C7 -20.1(10) . . . . ?
O2 C1 C2 C3 -9.1(10) . . . . ?
O2 C1 C2 C7 166.0(6) . . . . ?
C1 C2 C3 C4 170.4(6) . . . . ?
C1 C2 C7 N1 12.4(10) . . . . ?
C1 C2 C7 C6 -170.1(6) . . . . ?
C2 C3 C4 C5 8.7(11) . . . . ?
C2 C3 C4 C8 170.3(6) . . . . ?
C3 C2 C7 N1 -172.4(7) . . . . ?
C3 C2 C7 C6 5.2(10) . . . . ?
C3 C4 C5 C6 -13.8(14) . . . . ?
C3 C4 C8 Eu1 20.6(19) . . . 3_435 ?
C3 C4 C8 O3 2.3(11) . . . . ?
C3 C4 C8 O4 166.0(6) . . . . ?
C4 C5 C6 C7 14.5(14) . . . . ?
C4 C5 C6 C9 176.6(8) . . . . ?
C5 C4 C8 Eu1 -178.6(13) . . . 3_435 ?
C5 C4 C8 O3 163.0(9) . . . . ?
C5 C4 C8 O4 -33.2(10) . . . . ?
C5 C6 C7 N1 168.5(8) . . . . ?
C5 C6 C7 C2 -9.3(10) . . . . ?
C5 C6 C9 Eu1 153.4(8) . . . 2_354 ?
C5 C6 C9 O5 13.0(11) . . . . ?
C5 C6 C9 O6 171.4(7) . . . . ?
C7 C2 C3 C4 -4.5(10) . . . . ?
C7 C6 C9 Eu1 -45.5(12) . . . 2_354 ?
C7 C6 C9 O5 174.1(6) . . . . ?
C7 C6 C9 O6 -27.5(9) . . . . ?
C8 C4 C5 C6 -174.5(8) . . . . ?
C9 C6 C7 N1 7.3(9) . . . . ?
C9 C6 C7 C2 -170.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.571(4)
2 0.429(4)

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1957994'
loop_
_audit_author_name
_audit_author_address
'Zhan Shi'
; State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, College of Chemistry, Jilin 
China
;
_audit_update_record             
;
2019-10-08 deposited with the CCDC.	2019-11-17 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT213_2                   
;
PROBLEM: Atom O4              has ADP max/min Ratio .....        5.2 oblate
RESPONSE: The atom O4 has some disorder.
;
_vrf_PLAT602_2                   
; 
PROBLEM:  VERY LARGE Solvent Accessible VOID(S) in Structure ! Info 
RESPONSE: This alert is generated because the disorder molecule exist in the structure.
;
# end Validation Reply Form
_audit_creation_date             2019-10-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13.5 H16.5 Eu N2.5 O8.5'
_chemical_formula_sum            'C9 H3 Eu N O7'
_chemical_formula_weight         389.08
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x+1/2, z+3/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+1/4'
'x+1/2, -y+1/2, -z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   14.564(3)
_cell_length_b                   14.564(3)
_cell_length_c                   14.223(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3017.0(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9596
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      25.85
_cell_measurement_theta_min      2.80
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.177
_exptl_absorpt_correction_T_max  0.621
_exptl_absorpt_correction_T_min  0.413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   colorless
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25159
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.096
_diffrn_reflns_theta_min         2.797
_diffrn_ambient_temperature      299.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2720
_reflns_number_total             2989
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.891
_refine_diff_density_min         -0.829
_refine_diff_density_rms         0.170
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2989
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.130
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0624P)²+14.7295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1232
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N1) \\sim Ueq, Uanis(N1A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Sof(N1A)=Sof(H1AA)=Sof(H1AB)=1-FVAR(1)
 Sof(N1)=Sof(H1A)=Sof(H1B)=FVAR(1)
4.a Rotating group:
 N1(H1A,H1B)
4.b Aromatic/amide H refined with riding coordinates:
 C7(H7)
4.c X=CH2 refined with riding coordinates:
 N1A(H1AA,H1AB)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.51439(4) 0.13386(4) 0.37793(4) 0.0311(2) Uani 1 1 d . . . . .
O1 O 0.4288(9) 0.0099(8) 0.9107(9) 0.067(4) Uani 1 1 d . . . . .
O2 O 0.3472(11) 0.1048(8) 0.9937(7) 0.078(4) Uani 1 1 d . . . . .
O3 O 0.5252(11) 0.1012(8) 0.5883(11) 0.097(6) Uani 1 1 d . . . . .
O4 O 0.4346(13) 0.1793(15) 0.5105(8) 0.135(8) Uani 1 1 d . . . . .
O5 O 0.2246(9) 0.4016(9) 0.6904(7) 0.069(4) Uani 1 1 d . . . . .
O6 O 0.1617(9) 0.3383(11) 0.8146(7) 0.088(5) Uani 1 1 d . . . . .
O7 O 0.5517(16) 0.3033(13) 0.3947(16) 0.150(8) Uani 1 1 d . . . . .
C1 C 0.3813(12) 0.0834(11) 0.9173(10) 0.048(4) Uani 1 1 d . . . . .
C2 C 0.3694(11) 0.1408(11) 0.8348(8) 0.041(3) Uani 1 1 d . . . . .
C3 C 0.3068(12) 0.2147(12) 0.8358(9) 0.052(5) Uani 1 1 d . . . . .
C4 C 0.2948(11) 0.2697(12) 0.7534(9) 0.049(4) Uani 1 1 d . . . . .
C5 C 0.3428(13) 0.2471(12) 0.6729(9) 0.058(5) Uani 1 1 d . . . . .
C6 C 0.4078(12) 0.1742(11) 0.6743(8) 0.050(4) Uani 1 1 d . . . . .
C7 C 0.4198(11) 0.1245(10) 0.7538(9) 0.043(4) Uani 1 1 d . . . . .
H7 H 0.4634 0.0778 0.7541 0.052 Uiso 1 1 calc R . . . .
C8 C 0.4609(13) 0.1512(12) 0.5880(11) 0.062(5) Uani 1 1 d . . . . .
C9 C 0.2205(13) 0.3407(13) 0.7532(9) 0.057(5) Uani 1 1 d . . . . .
N1 N 0.343(2) 0.3019(18) 0.5945(15) 0.076(10) Uani 0.56(3) 1 d . U P A 1
H1A H 0.3736 0.2756 0.5490 0.091 Uiso 0.56(3) 1 d GR . P A 1
H1B H 0.2871 0.3119 0.5743 0.091 Uiso 0.56(3) 1 d GR . P A 1
N1A N 0.272(3) 0.234(3) 0.917(2) 0.072(11) Uani 0.44(3) 1 d . U P A 2
H1AA H 0.2882 0.2023 0.9659 0.087 Uiso 0.44(3) 1 calc R . P A 2
H1AB H 0.2338 0.2781 0.9231 0.087 Uiso 0.44(3) 1 calc R . P A 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 O1 2.299(12) 3_654 ?
Eu1 O2 2.335(10) 4_554 ?
Eu1 O3 3.033(15) . ?
Eu1 O3 2.378(14) 2_544 ?
Eu1 O4 2.311(12) . ?
Eu1 O5 2.321(10) 7_556 ?
Eu1 O6 2.332(11) 5_556 ?
Eu1 O7 2.538(19) . ?
Eu1 C1 3.168(14) 4_554 ?
Eu1 C8 3.099(14) . ?
O1 Eu1 2.299(12) 3_655 ?
O1 C1 1.28(2) . ?
O2 Eu1 2.335(10) 2_545 ?
O2 C1 1.234(19) . ?
O3 Eu1 2.378(14) 4 ?
O3 C8 1.19(2) . ?
O4 C8 1.24(2) . ?
O5 Eu1 2.321(10) 7_556 ?
O5 C9 1.260(18) . ?
O6 Eu1 2.332(11) 5_456 ?
O6 C9 1.223(18) . ?
C1 Eu1 3.168(14) 2_545 ?
C1 C2 1.451(17) . ?
C2 C3 1.41(2) . ?
C2 C7 1.387(18) . ?
C3 C4 1.431(19) . ?
C3 N1A 1.29(3) . ?
C4 C5 1.382(18) . ?
C4 C9 1.50(2) . ?
C5 C6 1.42(2) . ?
C5 N1 1.37(2) . ?
C6 C7 1.355(18) . ?
C6 C8 1.487(17) . ?
C7 H7 0.9300 . ?
N1 H1A 0.8741 . ?
N1 H1B 0.8757 . ?
N1A H1AA 0.8600 . ?
N1A H1AB 0.8600 . ?

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 O2 94.0(5) 3_654 4_554 ?
O1 Eu1 O3 72.4(5) 3_654 2_544 ?
O1 Eu1 O3 68.8(4) 3_654 . ?
O1 Eu1 O4 106.0(6) 3_654 . ?
O1 Eu1 O5 149.1(5) 3_654 7_556 ?
O1 Eu1 O6 75.9(5) 3_654 5_556 ?
O1 Eu1 O7 142.1(6) 3_654 . ?
O1 Eu1 C1 90.8(4) 3_654 4_554 ?
O1 Eu1 C8 88.2(4) 3_654 . ?
O2 Eu1 O3 142.7(4) 4_554 . ?
O2 Eu1 O3 106.5(5) 4_554 2_544 ?
O2 Eu1 O7 80.9(7) 4_554 . ?
O2 Eu1 C1 19.3(5) 4_554 4_554 ?
O2 Eu1 C8 157.0(5) 4_554 . ?
O3 Eu1 O3 99.6(4) 2_544 . ?
O3 Eu1 O7 145.2(6) 2_544 . ?
O3 Eu1 C1 87.4(5) 2_544 4_554 ?
O3 Eu1 C1 154.9(4) . 4_554 ?
O3 Eu1 C8 96.0(5) 2_544 . ?
O3 Eu1 C8 22.3(4) . . ?
O4 Eu1 O2 156.4(7) . 4_554 ?
O4 Eu1 O3 91.6(7) . 2_544 ?
O4 Eu1 O3 42.8(5) . . ?
O4 Eu1 O5 79.8(5) . 7_556 ?
O4 Eu1 O6 97.3(6) . 5_556 ?
O4 Eu1 O7 75.7(8) . . ?
O4 Eu1 C1 162.0(6) . 4_554 ?
O4 Eu1 C8 20.5(6) . . ?
O5 Eu1 O2 89.4(5) 7_556 4_554 ?
O5 Eu1 O3 77.2(5) 7_556 2_544 ?
O5 Eu1 O3 122.6(4) 7_556 . ?
O5 Eu1 O6 134.3(5) 7_556 5_556 ?
O5 Eu1 O7 68.7(6) 7_556 . ?
O5 Eu1 C1 82.4(4) 7_556 4_554 ?
O5 Eu1 C8 100.3(4) 7_556 . ?
O6 Eu1 O2 75.4(4) 5_556 4_554 ?
O6 Eu1 O3 68.5(4) 5_556 . ?
O6 Eu1 O3 148.2(5) 5_556 2_544 ?
O6 Eu1 O7 66.5(6) 5_556 . ?
O6 Eu1 C1 92.9(4) 5_556 4_554 ?
O6 Eu1 C8 83.1(5) 5_556 . ?
O7 Eu1 O3 92.8(6) . . ?
O7 Eu1 C1 95.1(6) . 4_554 ?
O7 Eu1 C8 83.3(6) . . ?
C8 Eu1 C1 176.0(5) . 4_554 ?
C1 O1 Eu1 166.5(12) . 3_655 ?
C1 O2 Eu1 122.0(11) . 2_545 ?
Eu1 O3 Eu1 112.3(4) 4 . ?
C8 O3 Eu1 82.0(11) . . ?
C8 O3 Eu1 163.8(11) . 4 ?
C8 O4 Eu1 118.5(14) . . ?
C9 O5 Eu1 140.1(11) . 7_556 ?
C9 O6 Eu1 152.7(10) . 5_456 ?
O1 C1 Eu1 80.9(9) . 2_545 ?
O1 C1 C2 119.2(14) . . ?
O2 C1 Eu1 38.7(8) . 2_545 ?
O2 C1 O1 119.5(14) . . ?
O2 C1 C2 121.3(15) . . ?
C2 C1 Eu1 159.9(11) . 2_545 ?
C3 C2 C1 120.6(12) . . ?
C7 C2 C1 120.6(13) . . ?
C7 C2 C3 118.8(12) . . ?
C2 C3 C4 119.9(12) . . ?
N1A C3 C2 115.1(17) . . ?
N1A C3 C4 124.5(19) . . ?
C3 C4 C9 118.5(12) . . ?
C5 C4 C3 118.9(12) . . ?
C5 C4 C9 121.9(12) . . ?
C4 C5 C6 120.2(11) . . ?
N1 C5 C4 122.4(16) . . ?
N1 C5 C6 116.4(15) . . ?
C5 C6 C8 120.1(12) . . ?
C7 C6 C5 119.8(12) . . ?
C7 C6 C8 120.1(13) . . ?
C2 C7 H7 118.9 . . ?
C6 C7 C2 122.3(13) . . ?
C6 C7 H7 118.9 . . ?
O3 C8 Eu1 75.7(9) . . ?
O3 C8 O4 116.7(15) . . ?
O3 C8 C6 123.1(16) . . ?
O4 C8 Eu1 41.0(9) . . ?
O4 C8 C6 120.0(16) . . ?
C6 C8 Eu1 160.8(12) . . ?
O5 C9 C4 117.0(14) . . ?
O6 C9 O5 124.0(15) . . ?
O6 C9 C4 119.0(14) . . ?
C5 N1 H1A 110.4 . . ?
C5 N1 H1B 111.2 . . ?
H1A N1 H1B 107.7 . . ?
C3 N1A H1AA 120.0 . . ?
C3 N1A H1AB 120.0 . . ?
H1AA N1A H1AB 120.0 . . ?

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 O1 C1 Eu1 111(5) 3_655 . . 2_545 ?
Eu1 O1 C1 O2 111(5) 3_655 . . . ?
Eu1 O1 C1 C2 -70(5) 3_655 . . . ?
Eu1 O2 C1 O1 0(2) 2_545 . . . ?
Eu1 O2 C1 C2 -179.5(11) 2_545 . . . ?
Eu1 O3 C8 Eu1 -153(6) 4 . . . ?
Eu1 O3 C8 O4 0.7(19) . . . . ?
Eu1 O3 C8 O4 -152(5) 4 . . . ?
Eu1 O3 C8 C6 176(2) . . . . ?
Eu1 O3 C8 C6 23(7) 4 . . . ?
Eu1 O4 C8 O3 -1(3) . . . . ?
Eu1 O4 C8 C6 -176.2(14) . . . . ?
Eu1 O5 C9 O6 -17(4) 7_556 . . . ?
Eu1 O5 C9 C4 165.6(14) 7_556 . . . ?
Eu1 O6 C9 O5 30(5) 5_456 . . . ?
Eu1 O6 C9 C4 -152(2) 5_456 . . . ?
Eu1 C1 C2 C3 -11(4) 2_545 . . . ?
Eu1 C1 C2 C7 169(2) 2_545 . . . ?
O1 C1 C2 C3 170.6(17) . . . . ?
O1 C1 C2 C7 -10(2) . . . . ?
O2 C1 C2 C3 -10(3) . . . . ?
O2 C1 C2 C7 169.4(17) . . . . ?
C1 C2 C3 C4 -179.0(17) . . . . ?
C1 C2 C3 N1A 9(3) . . . . ?
C1 C2 C7 C6 177.2(17) . . . . ?
C2 C3 C4 C5 2(3) . . . . ?
C2 C3 C4 C9 173.2(18) . . . . ?
C3 C2 C7 C6 -3(3) . . . . ?
C3 C4 C5 C6 -4(3) . . . . ?
C3 C4 C5 N1 -173(2) . . . . ?
C3 C4 C9 O5 164.0(18) . . . . ?
C3 C4 C9 O6 -14(3) . . . . ?
C4 C5 C6 C7 3(3) . . . . ?
C4 C5 C6 C8 -178.7(19) . . . . ?
C5 C4 C9 O5 -25(3) . . . . ?
C5 C4 C9 O6 157(2) . . . . ?
C5 C6 C7 C2 1(3) . . . . ?
C5 C6 C8 Eu1 -25(5) . . . . ?
C5 C6 C8 O3 168(2) . . . . ?
C5 C6 C8 O4 -17(3) . . . . ?
C7 C2 C3 C4 1(3) . . . . ?
C7 C2 C3 N1A -170(3) . . . . ?
C7 C6 C8 Eu1 154(3) . . . . ?
C7 C6 C8 O3 -13(3) . . . . ?
C7 C6 C8 O4 162(2) . . . . ?
C8 C6 C7 C2 -177.3(17) . . . . ?
C9 C4 C5 C6 -175.0(19) . . . . ?
C9 C4 C5 N1 17(4) . . . . ?
N1 C5 C6 C7 172(2) . . . . ?
N1 C5 C6 C8 -10(3) . . . . ?
N1A C3 C4 C5 173(3) . . . . ?
N1A C3 C4 C9 -16(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
