# 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_exp_2419
_database_code_depnum_ccdc_archive 'CCDC 2023256'
loop_
_audit_author_name
_audit_author_address
'Min-Le Han' 'Luoyang Normal University'
_audit_update_record             
;
2020-08-14 deposited with the CCDC.	2020-10-01 downloaded from the CCDC.
;
_audit_creation_date             2020-06-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H7 Eu N O5'
_chemical_formula_sum            'C13 H7 Eu N O5'
_chemical_formula_weight         409.16
_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 0.0181 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'
Eu Eu -8.9294 11.1857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'

_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           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   30.3039(3)
_cell_length_b                   30.3039(3)
_cell_length_c                   8.27250(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7596.85(18)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    6033
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.0660
_cell_measurement_theta_min      5.5330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    23.771
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             3120
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8555
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.581
_diffrn_reflns_theta_max         66.581
_diffrn_reflns_theta_min         4.126
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  17.00   0.50    3.39    --    0.00 -82.00 150.00   94
  2  ω    -33.00   2.00   0.50    3.39    --    0.00 -82.00  60.00   70
  3  ω      6.00 105.00   0.50   13.55    --   95.80 -77.00 120.00  198
  4  ω    143.00 181.00   0.50   13.55    --   95.80  82.00 120.00   76
  5  ω    100.00 130.00   0.50   13.55    --   95.80  82.00 120.00   60
  6  ω     89.00 142.00   0.50   13.55    --   95.80  82.00-150.00  106
  7  ω     90.00 120.00   0.50   13.55    --   95.80  77.00-180.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0116878000
_diffrn_orient_matrix_UB_12      -0.0122893000
_diffrn_orient_matrix_UB_13      -0.1755560000
_diffrn_orient_matrix_UB_21      -0.0363788000
_diffrn_orient_matrix_UB_22      0.0355336000
_diffrn_orient_matrix_UB_23      -0.0008726000
_diffrn_orient_matrix_UB_31      0.0335231000
_diffrn_orient_matrix_UB_32      0.0342237000
_diffrn_orient_matrix_UB_33      -0.0621301000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3085
_reflns_number_total             3336
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.120
_refine_diff_density_min         -0.857
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3336
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+0.4600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0872
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C3(H3), C12(H12), C4(H4), C7(H7), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.52648(2) 0.69253(2) 0.46044(2) 0.01655(11) Uani 1 1 d . . . . .
O5 O 0.41654(9) 0.28212(9) 1.0308(2) 0.0261(5) Uani 1 1 d . . . . .
O3 O 0.45982(8) 0.73105(7) 0.5070(2) 0.0198(5) Uani 1 1 d . . . . .
O4 O 0.43964(9) 0.27736(8) 0.7755(2) 0.0267(6) Uani 1 1 d . . . . .
O2 O 0.44090(10) 0.64761(9) 0.7052(3) 0.0347(6) Uani 1 1 d . . . . .
O1 O 0.50408(9) 0.62600(8) 0.5905(3) 0.0327(6) Uani 1 1 d . . . . .
N1 N 0.44127(10) 0.36437(10) 0.7415(3) 0.0255(6) Uani 1 1 d . . . . .
C13 C 0.42762(11) 0.29837(11) 0.8974(3) 0.0209(7) Uani 1 1 d . . . . .
C10 C 0.42786(12) 0.34835(11) 0.8841(3) 0.0251(8) Uani 1 1 d . . . . .
C9 C 0.44607(14) 0.40741(12) 0.7270(4) 0.0312(8) Uani 1 1 d . . . . .
H9 H 0.4552 0.4184 0.6275 0.037 Uiso 1 1 calc R . . . .
C1 C 0.46948(13) 0.61905(11) 0.6716(4) 0.0270(8) Uani 1 1 d . . . . .
C11 C 0.41800(15) 0.37571(13) 1.0134(4) 0.0369(9) Uani 1 1 d . . . . .
H11 H 0.4081 0.3638 1.1104 0.044 Uiso 1 1 calc R . . . .
C8 C 0.43839(14) 0.43759(13) 0.8508(4) 0.0364(9) Uani 1 1 d . . . . .
C2 C 0.46243(15) 0.57275(13) 0.7317(4) 0.0348(9) Uani 1 1 d . . . . .
C3 C 0.49262(16) 0.54010(14) 0.6919(5) 0.0421(10) Uani 1 1 d . . . . .
H3 H 0.5181 0.5474 0.6352 0.051 Uiso 1 1 calc R . . . .
C12 C 0.42301(17) 0.42063(14) 0.9974(5) 0.0448(11) Uani 1 1 d . . . . .
H12 H 0.4163 0.4394 1.0828 0.054 Uiso 1 1 calc R . . . .
C5 C 0.44742(16) 0.48519(13) 0.8200(5) 0.0403(10) Uani 1 1 d . . . . .
C4 C 0.48509(16) 0.49691(14) 0.7359(5) 0.0437(11) Uani 1 1 d . . . . .
H4 H 0.5056 0.4753 0.7086 0.052 Uiso 1 1 calc R . . . .
C7 C 0.42620(17) 0.56155(14) 0.8231(6) 0.0549(13) Uani 1 1 d . . . . .
H7 H 0.4066 0.5834 0.8562 0.066 Uiso 1 1 calc R . . . .
C6 C 0.41867(19) 0.51803(15) 0.8662(6) 0.0640(15) Uani 1 1 d . . . . .
H6 H 0.3939 0.5109 0.9271 0.077 Uiso 1 1 calc R . . . .


_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 Eu1 3.8346(4) 6_564 ?
Eu1 Eu1 3.8424(3) 15_566 ?
Eu1 Eu1 3.8425(3) 12_767 ?
Eu1 O5 2.446(2) 3_554 ?
Eu1 O3 2.364(2) . ?
Eu1 O3 2.384(2) 6_564 ?
Eu1 O3 2.406(2) 12_767 ?
Eu1 O4 2.387(2) 9_666 ?
Eu1 O2 2.404(3) 12_767 ?
Eu1 O1 2.384(2) . ?
Eu1 N1 2.593(3) 9_666 ?
O5 Eu1 2.446(2) 4_455 ?
O5 C13 1.254(4) . ?
O3 Eu1 2.384(2) 6_564 ?
O3 Eu1 2.406(2) 15_566 ?
O4 Eu1 2.387(2) 9_666 ?
O4 C13 1.247(4) . ?
O2 Eu1 2.404(3) 15_566 ?
O2 C1 1.256(4) . ?
O1 C1 1.263(4) . ?
N1 Eu1 2.593(3) 9_666 ?
N1 C10 1.338(4) . ?
N1 C9 1.318(5) . ?
C13 C10 1.519(5) . ?
C10 C11 1.386(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.392(5) . ?
C1 C2 1.504(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(6) . ?
C8 C12 1.397(5) . ?
C8 C5 1.490(5) . ?
C2 C3 1.388(6) . ?
C2 C7 1.376(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(6) . ?
C12 H12 0.9300 . ?
C5 C4 1.383(6) . ?
C5 C6 1.377(6) . ?
C4 H4 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.385(6) . ?
C6 H6 0.9300 . ?

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
Eu1 Eu1 Eu1 59.864(5) 15_566 12_767 ?
Eu1 Eu1 Eu1 60.067(2) 6_564 15_566 ?
Eu1 Eu1 Eu1 60.066(2) 6_564 12_767 ?
O5 Eu1 Eu1 145.20(6) 3_554 12_767 ?
O5 Eu1 Eu1 89.35(6) 3_554 6_564 ?
O5 Eu1 Eu1 91.64(6) 3_554 15_566 ?
O5 Eu1 N1 70.61(8) 3_554 9_666 ?
O3 Eu1 Eu1 35.97(5) 6_564 6_564 ?
O3 Eu1 Eu1 76.50(5) . 12_767 ?
O3 Eu1 Eu1 76.31(5) 6_564 15_566 ?
O3 Eu1 Eu1 36.47(5) 12_767 15_566 ?
O3 Eu1 Eu1 35.97(5) 12_767 12_767 ?
O3 Eu1 Eu1 36.85(5) 6_564 12_767 ?
O3 Eu1 Eu1 76.26(5) 12_767 6_564 ?
O3 Eu1 Eu1 36.31(5) . 6_564 ?
O3 Eu1 Eu1 36.71(5) . 15_566 ?
O3 Eu1 O5 126.27(8) 12_767 3_554 ?
O3 Eu1 O5 122.51(8) 6_564 3_554 ?
O3 Eu1 O5 68.76(8) . 3_554 ?
O3 Eu1 O3 69.38(8) 6_564 12_767 ?
O3 Eu1 O3 69.08(9) . 6_564 ?
O3 Eu1 O3 69.71(8) . 12_767 ?
O3 Eu1 O4 71.69(8) 6_564 9_666 ?
O3 Eu1 O4 108.19(8) . 9_666 ?
O3 Eu1 O2 78.84(9) 6_564 12_767 ?
O3 Eu1 O2 141.28(8) . 12_767 ?
O3 Eu1 O1 142.96(7) 6_564 . ?
O3 Eu1 O1 95.78(9) . . ?
O3 Eu1 N1 139.07(9) . 9_666 ?
O3 Eu1 N1 133.21(9) 6_564 9_666 ?
O3 Eu1 N1 143.77(8) 12_767 9_666 ?
O4 Eu1 Eu1 80.38(6) 9_666 6_564 ?
O4 Eu1 Eu1 102.77(6) 9_666 12_767 ?
O4 Eu1 Eu1 140.43(6) 9_666 15_566 ?
O4 Eu1 O5 86.49(8) 9_666 3_554 ?
O4 Eu1 O3 138.75(8) 9_666 12_767 ?
O4 Eu1 O2 80.41(9) 9_666 12_767 ?
O4 Eu1 N1 64.22(9) 9_666 9_666 ?
O2 Eu1 Eu1 64.80(6) 12_767 12_767 ?
O2 Eu1 Eu1 114.77(7) 12_767 6_564 ?
O2 Eu1 Eu1 115.65(6) 12_767 15_566 ?
O2 Eu1 O5 149.80(9) 12_767 3_554 ?
O2 Eu1 O3 79.24(8) 12_767 12_767 ?
O2 Eu1 N1 79.20(9) 12_767 9_666 ?
O1 Eu1 Eu1 130.47(6) . 6_564 ?
O1 Eu1 Eu1 108.05(6) . 12_767 ?
O1 Eu1 Eu1 72.46(6) . 15_566 ?
O1 Eu1 O5 78.17(8) . 3_554 ?
O1 Eu1 O3 73.68(8) . 12_767 ?
O1 Eu1 O4 144.57(8) . 9_666 ?
O1 Eu1 O2 97.13(10) . 12_767 ?
O1 Eu1 N1 80.53(9) . 9_666 ?
N1 Eu1 Eu1 143.60(7) 9_666 12_767 ?
N1 Eu1 Eu1 139.63(6) 9_666 6_564 ?
N1 Eu1 Eu1 150.32(7) 9_666 15_566 ?
C13 O5 Eu1 137.2(2) . 4_455 ?
Eu1 O3 Eu1 107.31(8) . 15_566 ?
Eu1 O3 Eu1 107.72(9) . 6_564 ?
Eu1 O3 Eu1 106.68(8) 6_564 15_566 ?
C13 O4 Eu1 126.3(2) . 9_666 ?
C1 O2 Eu1 135.2(3) . 15_566 ?
C1 O1 Eu1 128.1(2) . . ?
C10 N1 Eu1 116.2(2) . 9_666 ?
C9 N1 Eu1 123.9(2) . 9_666 ?
C9 N1 C10 118.2(3) . . ?
O5 C13 C10 117.2(3) . . ?
O4 C13 O5 126.1(3) . . ?
O4 C13 C10 116.7(3) . . ?
N1 C10 C13 115.3(3) . . ?
N1 C10 C11 121.9(3) . . ?
C11 C10 C13 122.6(3) . . ?
N1 C9 H9 117.8 . . ?
N1 C9 C8 124.4(3) . . ?
C8 C9 H9 117.8 . . ?
O2 C1 O1 125.2(3) . . ?
O2 C1 C2 118.1(3) . . ?
O1 C1 C2 116.7(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C9 C8 C12 116.9(4) . . ?
C9 C8 C5 118.7(3) . . ?
C12 C8 C5 124.4(3) . . ?
C3 C2 C1 119.6(4) . . ?
C7 C2 C1 121.7(4) . . ?
C7 C2 C3 118.7(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(4) . . ?
C4 C3 H3 119.8 . . ?
C11 C12 C8 119.0(4) . . ?
C11 C12 H12 120.5 . . ?
C8 C12 H12 120.5 . . ?
C4 C5 C8 119.1(4) . . ?
C6 C5 C8 122.4(4) . . ?
C6 C5 C4 118.4(4) . . ?
C3 C4 C5 120.9(4) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C2 C7 H7 119.7 . . ?
C2 C7 C6 120.5(4) . . ?
C6 C7 H7 119.7 . . ?
C5 C6 C7 120.8(4) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.575
_oxdiff_exptl_absorpt_empirical_full_min 0.350
