# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_UPC-38-OCH3
_database_code_depnum_ccdc_archive 'CCDC 1951706'
loop_
_audit_author_name
_audit_author_address
'wang yutong'
;China University of Petroleum(East China)
China
;
_audit_update_record             
;
2019-09-09 deposited with the CCDC.	2019-12-06 downloaded from the CCDC.
;
_audit_creation_date             2019-09-09
_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         'C11.5 H7 Eu0.5 O4.5, C3 H7 N O'
_chemical_formula_sum            'C14.50 H14 Eu0.50 N O5.50'
_chemical_formula_weight         366.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O Eu'
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/c 1'
_space_group_name_Hall           '-I 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   9.5566(3)
_cell_length_b                   18.5611(6)
_cell_length_c                   16.0663(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.120(3)
_cell_angle_gamma                90
_cell_volume                     2845.64(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3307
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      69.1960
_cell_measurement_theta_min      4.7590
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    16.350
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1468
_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  0.0355
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5220
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.522
_diffrn_reflns_theta_min         3.642
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  36.00   1.00    4.45    --    0.00 -85.00   5.00   51
  2  ω    -22.00  69.00   1.00    4.45    --    0.00  57.00-150.00   91
  3  ω    -22.00  16.00   1.00    4.45    --    0.00  85.00 124.00   38
  4  ω     37.00 122.00   1.00   10.00    --   53.47  38.00  30.00   85
  5  ω     32.00 111.00   1.00   10.00    --   53.47  57.00 120.00   79
  6  ω      2.00  96.00   1.00   10.00    --   53.47 -99.00-120.00   94
  7  ω    100.00 174.00   1.00   12.50    --  106.95 111.00  90.00   74
  8  ω     39.00 104.00   1.00   12.50    --  106.95-111.00 -90.00   65
  9  ω    104.00 172.00   1.00   12.50    --  106.95  63.00   0.00   68
 10  ω     40.00 118.00   1.00   12.50    --  106.95 -63.00  60.00   78
 11  ω     55.00  84.00   1.00   12.50    --  106.95-111.00 -60.00   29
 12  ω     68.00  97.00   1.00   12.50    --  106.95 178.00 120.00   29
 13  ω     39.00 110.00   1.00   12.50    --  106.95 -77.00   0.00   71
 14  ω     86.00 177.00   1.00   12.50    --  106.95  38.00  90.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1205244000
_diffrn_orient_matrix_UB_12      -0.0317401000
_diffrn_orient_matrix_UB_13      -0.0562540000
_diffrn_orient_matrix_UB_21      -0.0048844000
_diffrn_orient_matrix_UB_22      -0.0663107000
_diffrn_orient_matrix_UB_23      0.0574261000
_diffrn_orient_matrix_UB_31      -0.1072259000
_diffrn_orient_matrix_UB_32      0.0384406000
_diffrn_orient_matrix_UB_33      0.0526766000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2470
_reflns_number_total             2569
_reflns_odcompleteness_completeness 95.36
_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.
 
 _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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.762
_refine_diff_density_min         -1.201
_refine_diff_density_rms         0.146
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2569
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0578
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²+57.4977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1416
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Rotating group:
 O4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C3(H3), C8(H8), C7(H7), C14(H14)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.0000 0.77538(3) 0.2500 0.01756(19) Uani 1 2 d S T P . .
O1 O -0.0801(6) 0.6543(3) 0.2968(3) 0.0327(12) Uani 1 1 d . . . . .
O2 O 0.1135(6) 0.8069(4) 0.1271(4) 0.0473(17) Uani 1 1 d . . . . .
O4 O 0.1376(6) 0.8817(3) 0.2928(4) 0.0443(15) Uani 1 1 d . . . . .
H4A H 0.1239 0.9171 0.2570 0.066 Uiso 1 1 d GR . . . .
H4B H 0.2276 0.8715 0.2959 0.066 Uiso 1 1 d GR . . . .
O3 O 0.3176(6) 0.7583(4) 0.1572(4) 0.0435(15) Uani 1 1 d . . . . .
C12 C 0.2902(7) 0.8255(4) 0.0324(4) 0.0253(15) Uani 1 1 d . . . . .
C4 C 0.0541(9) 0.4281(4) 0.1831(5) 0.0336(18) Uani 1 1 d . . . . .
C9 C 0.0766(11) 0.3177(9) -0.0127(8) 0.092(5) Uani 1 1 d . . . . .
H9 H 0.0166 0.2898 -0.0469 0.110 Uiso 1 1 calc R . . . .
C6 C 0.1083(9) 0.3892(4) 0.1102(5) 0.0307(17) Uani 1 1 d . . . . .
C11 C 0.2352(7) 0.7941(4) 0.1108(4) 0.0234(14) Uani 1 1 d . . . . .
C13 C 0.2067(12) 0.8615(11) -0.0221(9) 0.120(8) Uani 1 1 d . . . . .
H13 H 0.1126 0.8667 -0.0113 0.144 Uiso 1 1 calc R . . . .
C3 C 0.0545(8) 0.5030(4) 0.1845(4) 0.0271(15) Uani 1 1 d . . . . .
H3 H 0.0918 0.5285 0.1410 0.033 Uiso 1 1 calc R . . . .
C1 C 0.0000 0.6198(5) 0.2500 0.029(2) Uani 1 2 d S T P . .
C5 C 0.0000 0.3909(6) 0.2500 0.047(4) Uani 1 2 d S T P . .
C2 C 0.0000 0.5400(5) 0.2500 0.025(2) Uani 1 2 d S T P . .
N1 N -0.3468(13) 0.4243(8) 0.0816(11) 0.110(5) Uani 1 1 d . . . . .
C8 C 0.0253(12) 0.3500(10) 0.0569(8) 0.099(6) Uani 1 1 d . . . . .
H8 H -0.0689 0.3446 0.0672 0.119 Uiso 1 1 calc R . . . .
C7 C 0.2450(13) 0.3915(11) 0.0945(9) 0.126(8) Uani 1 1 d . . . . .
H7 H 0.3081 0.4136 0.1326 0.151 Uiso 1 1 calc R . . . .
C16 C -0.344(2) 0.4253(11) -0.0209(13) 0.127(7) Uiso 1 1 d . . . . .
H16A H -0.4173 0.4561 -0.0435 0.190 Uiso 1 1 calc GR . . . .
H16B H -0.3581 0.3773 -0.0420 0.190 Uiso 1 1 calc GR . . . .
H16C H -0.2550 0.4430 -0.0368 0.190 Uiso 1 1 calc GR . . . .
C14 C -0.347(2) 0.4844(13) 0.1242(15) 0.129(7) Uiso 1 1 d . . . . .
H14 H -0.3249 0.5274 0.0983 0.155 Uiso 1 1 calc R . . . .
C15 C -0.365(3) 0.3625(14) 0.1281(16) 0.161(9) Uiso 1 1 d . . . . .
H15A H -0.4100 0.3263 0.0935 0.241 Uiso 1 1 calc GR . . . .
H15B H -0.4220 0.3733 0.1738 0.241 Uiso 1 1 calc GR . . . .
H15C H -0.2752 0.3452 0.1492 0.241 Uiso 1 1 calc GR . . . .
O6 O -0.381(3) 0.4854(14) 0.2073(16) 0.250(11) Uiso 1 1 d . . . . .
C10 C -0.102(4) 0.2911(18) 0.233(2) 0.215(14) Uiso 1 1 d . . . . .
O5 O 0.0000 0.3180(9) 0.2500 0.099(5) Uiso 1 2 d S T P . .


_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 2.503(5) . ?
Eu1 O1 2.503(5) 2 ?
Eu1 O2 2.377(5) . ?
Eu1 O2 2.377(5) 2 ?
Eu1 O4 2.449(5) 2 ?
Eu1 O4 2.449(5) . ?
Eu1 O3 2.317(6) 8_465 ?
Eu1 O3 2.317(6) 7_565 ?
Eu1 C1 2.887(10) . ?
O1 C1 1.274(7) . ?
O2 C11 1.229(9) . ?
O3 Eu1 2.317(5) 7_565 ?
O3 C11 1.247(9) . ?
C12 C9 1.336(13) 4_554 ?
C12 C11 1.508(9) . ?
C12 C13 1.332(13) . ?
C4 C6 1.493(10) . ?
C4 C3 1.391(11) . ?
C4 C5 1.400(9) . ?
C9 C12 1.336(12) 4_544 ?
C9 C8 1.382(13) . ?
C6 C8 1.348(14) . ?
C6 C7 1.344(14) . ?
C13 C7 1.392(14) 4_554 ?
C3 C2 1.382(8) . ?
C1 O1 1.274(7) 2 ?
C1 C2 1.483(14) . ?
C5 C4 1.400(9) 2 ?
C5 O5 1.354(19) . ?
C2 C3 1.382(8) 2 ?
N1 C16 1.65(2) . ?
N1 C14 1.31(2) . ?
N1 C15 1.38(3) . ?
C7 C13 1.392(14) 4_544 ?
C14 O6 1.39(3) . ?
C10 C10 1.99(7) 2 ?
C10 O5 1.12(3) . ?
O5 C10 1.12(3) 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
O1 Eu1 O1 52.2(2) . 2 ?
O1 Eu1 C1 26.11(11) . . ?
O1 Eu1 C1 26.11(11) 2 . ?
O2 Eu1 O1 79.10(19) . 2 ?
O2 Eu1 O1 79.10(19) 2 . ?
O2 Eu1 O1 129.2(2) . . ?
O2 Eu1 O1 129.2(2) 2 2 ?
O2 Eu1 O2 151.5(3) . 2 ?
O2 Eu1 O4 80.2(2) 2 . ?
O2 Eu1 O4 80.2(2) . 2 ?
O2 Eu1 O4 76.8(2) 2 2 ?
O2 Eu1 O4 76.8(2) . . ?
O2 Eu1 C1 104.26(16) . . ?
O2 Eu1 C1 104.26(16) 2 . ?
O4 Eu1 O1 143.8(2) . . ?
O4 Eu1 O1 129.75(18) . 2 ?
O4 Eu1 O1 129.75(18) 2 . ?
O4 Eu1 O1 143.8(2) 2 2 ?
O4 Eu1 O4 72.7(3) . 2 ?
O4 Eu1 C1 143.67(14) 2 . ?
O4 Eu1 C1 143.67(14) . . ?
O3 Eu1 O1 78.2(2) 8_465 2 ?
O3 Eu1 O1 78.2(2) 7_565 . ?
O3 Eu1 O1 73.7(2) 8_465 . ?
O3 Eu1 O1 73.7(2) 7_565 2 ?
O3 Eu1 O2 103.8(2) 8_465 2 ?
O3 Eu1 O2 83.9(2) 8_465 . ?
O3 Eu1 O2 83.9(2) 7_565 2 ?
O3 Eu1 O2 103.8(2) 7_565 . ?
O3 Eu1 O4 70.3(2) 8_465 2 ?
O3 Eu1 O4 140.5(2) 8_465 . ?
O3 Eu1 O4 70.3(2) 7_565 . ?
O3 Eu1 O4 140.5(2) 7_565 2 ?
O3 Eu1 O3 148.7(3) 8_465 7_565 ?
O3 Eu1 C1 74.35(17) 8_465 . ?
O3 Eu1 C1 74.35(17) 7_565 . ?
C1 O1 Eu1 94.0(5) . . ?
C11 O2 Eu1 127.6(5) . . ?
C11 O3 Eu1 163.2(6) . 7_565 ?
C9 C12 C11 122.4(7) 4_554 . ?
C13 C12 C9 116.3(8) . 4_554 ?
C13 C12 C11 121.3(7) . . ?
C3 C4 C6 119.7(6) . . ?
C3 C4 C5 118.8(7) . . ?
C5 C4 C6 121.5(7) . . ?
C12 C9 C8 121.9(10) 4_544 . ?
C8 C6 C4 122.8(8) . . ?
C7 C6 C4 120.9(8) . . ?
C7 C6 C8 116.3(8) . . ?
O2 C11 O3 123.3(6) . . ?
O2 C11 C12 118.7(6) . . ?
O3 C11 C12 117.9(6) . . ?
C12 C13 C7 122.4(10) . 4_554 ?
C2 C3 C4 120.5(7) . . ?
O1 C1 Eu1 59.9(4) . . ?
O1 C1 Eu1 59.9(4) 2 . ?
O1 C1 O1 119.7(9) 2 . ?
O1 C1 C2 120.1(4) 2 . ?
O1 C1 C2 120.1(4) . . ?
C2 C1 Eu1 180.0 . . ?
C4 C5 C4 120.9(10) . 2 ?
O5 C5 C4 119.5(5) . . ?
O5 C5 C4 119.5(5) . 2 ?
C3 C2 C3 120.5(9) 2 . ?
C3 C2 C1 119.7(5) . . ?
C3 C2 C1 119.7(5) 2 . ?
C14 N1 C16 120.9(17) . . ?
C14 N1 C15 115(2) . . ?
C15 N1 C16 123.8(18) . . ?
C6 C8 C9 121.7(10) . . ?
C6 C7 C13 120.9(10) . 4_544 ?
N1 C14 O6 121(2) . . ?
O5 C10 C10 27(2) . 2 ?
C10 O5 C5 117(2) 2 . ?
C10 O5 C5 117(2) . . ?
C10 O5 C10 127(4) . 2 ?

_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 1.530
_oxdiff_exptl_absorpt_empirical_full_min 0.765
####################################################################### 
# 
# 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_UPC-38-Cl
_database_code_depnum_ccdc_archive 'CCDC 1951710'
loop_
_audit_author_name
_audit_author_address
'wang yutong'
;China University of Petroleum(East China)
China
;
_audit_update_record             
;
2019-09-05 deposited with the CCDC.	2019-12-06 downloaded from the CCDC.
;
_audit_creation_date             2019-09-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.25(C84 H56 Cl4 Eu4 O32)'
_chemical_formula_sum            'C21 H14 Cl Eu O8'
_chemical_formula_weight         581.73
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Cl Eu'
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'
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'
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/c 1'
_space_group_name_Hall           '-I 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   9.6229(3)
_cell_length_b                   19.5443(6)
_cell_length_c                   16.2189(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.742(3)
_cell_angle_gamma                90
_cell_volume                     3050.09(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5037
_cell_measurement_temperature    150
_cell_measurement_theta_max      69.8470
_cell_measurement_theta_min      4.5100
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    15.812
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.16033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_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  0.0621
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8417
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.455
_diffrn_reflns_theta_min         3.541
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -22.00  69.00   1.00    5.00    --    0.00  57.00-150.00   91
  2  ω    -22.00  69.00   1.00    5.00    --    0.00  57.00 -30.00   91
  3  ω     22.00 124.00   1.00   12.50    --   53.47  77.00 150.00  102
  4  ω     32.00 123.00   1.00   12.50    --   53.47  57.00-150.00   91
  5  ω     23.00 112.00   1.00   12.50    --   53.47-125.00 -90.00   89
  6  ω      1.00  97.00   1.00   12.50    --   53.47 -99.00  30.00   96
  7  ω     84.00 178.00   1.00   12.50    --  106.95  50.00-120.00   94
  8  ω     34.00 134.00   1.00   12.50    --  106.95 -38.00 -90.00  100
  9  ω     34.00 112.00   1.00   12.50    --  106.95-111.00 -90.00   78
 10  ω     37.00 111.00   1.00   12.50    --  106.95-111.00   0.00   74
 11  ω    101.00 150.00   1.00   12.50    --  106.95 111.00  60.00   49
 12  ω    101.00 170.00   1.00   12.50    --  106.95 111.00 -60.00   69
 13  ω    106.00 178.00   1.00   12.50    --  106.95 111.00 -30.00   72
 14  ω     93.00 164.00   1.00   12.50    --  106.95  50.00 120.00   71
 15  ω      7.00  51.00   1.00    5.00    --    0.00  57.00  60.00   44
 16  ω     37.00 104.00   1.00   12.50    --   53.47  57.00  90.00   67
 17  ω     73.00 113.00   1.00   12.50    --   53.47  57.00 -60.00   40
 18  ω     -5.00  75.00   1.00   12.50    --   53.47 -57.00-120.00   80
 19  ω     34.00  60.00   1.00   12.50    --  106.95-111.00-180.00   26
 20  ω     72.00 105.00   1.00   12.50    --  106.95-111.00-180.00   33
 21  ω     73.00  93.00   1.00   12.50    --  106.95-111.00  90.00   20
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0892452000
_diffrn_orient_matrix_UB_12      0.0549669000
_diffrn_orient_matrix_UB_13      -0.0433573000
_diffrn_orient_matrix_UB_21      -0.0972722000
_diffrn_orient_matrix_UB_22      0.0020135000
_diffrn_orient_matrix_UB_23      0.0746032000
_diffrn_orient_matrix_UB_31      0.0905911000
_diffrn_orient_matrix_UB_32      0.0564939000
_diffrn_orient_matrix_UB_33      0.0396672000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2603
_reflns_number_total             2857
_reflns_odcompleteness_completeness 99.61
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    ?
_refine_diff_density_max         2.722
_refine_diff_density_min         -1.267
_refine_diff_density_rms         0.172
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2857
_refine_ls_number_restraints     87
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0592
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0959P)²+29.9341P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1572
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C16) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 Cl3, C3, C6, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: Cl3(0.5) C3(0.5) C6(0.5) H6(0.5) C8(0.5) C9(0.5) C10(0.5) H10(0.5)
 C11(0.5) H11(0.5) C12(0.5) H12(0.5) C13(0.5) H13(0.5) C14(0.5) H14(0.5)
 C15(0.5) C16(0.5) C17(0.5) H17(0.5) C18(0.5) H18(0.5)
5.a Riding coordinates:
 O4(H4A,H4B), C5(H5), C13(H13), C14(H14), C17(H17), C18(H18)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.000000 0.23754(2) 0.750000 0.0137(2) Uani 1 2 d S T P . .
O1 O -0.0814(5) 0.6474(2) 0.2013(3) 0.0206(10) Uani 1 1 d . . . . .
Cl3 Cl 0.0518(4) 0.30979(16) 0.2373(2) 0.0279(8) Uani 0.5 1 d . U . A -1
O4 O 0.1333(5) 0.1370(3) 0.7175(3) 0.0263(11) Uani 1 1 d . . . . .
H4A H 0.154216 0.113971 0.762193 0.039 Uiso 1 1 d R . . . .
H4B H 0.214526 0.148561 0.698403 0.039 Uiso 1 1 d R . . . .
O6 O 0.1774(6) 0.2722(3) 0.6625(3) 0.0285(12) Uani 1 1 d . . . . .
O7 O 0.3918(5) 0.2923(3) 0.6214(3) 0.0259(11) Uani 1 1 d . . . . .
C1 C 0.000000 0.5403(5) 0.250000 0.0184(19) Uani 1 2 d S T P . .
C2 C 0.000000 0.6158(5) 0.250000 0.0184(19) Uani 1 2 d S T P . .
C3 C 0.0780(19) 0.4329(12) 0.3121(12) 0.024(4) Uani 0.5 1 d . U . A -1
C4 C 0.2069(8) 0.3325(4) 0.5371(5) 0.0277(17) Uani 1 1 d . . . . .
C5 C 0.0542(8) 0.5035(4) 0.3170(4) 0.0285(17) Uani 1 1 d . . . . .
H5 H 0.092187 0.528868 0.364310 0.034 Uiso 1 1 d R . . A .
C6 C 0.0848(18) 0.3583(10) 0.5255(10) 0.025(4) Uani 0.5 1 d . U . A -1
H6 H 0.020355 0.353988 0.567455 0.030 Uiso 0.5 1 calc R . . A -1
C7 C 0.2629(7) 0.2965(3) 0.6120(4) 0.0177(13) Uani 1 1 d . . . . .
C8 C 0.1358(19) 0.3941(10) 0.3868(11) 0.020(3) Uani 0.5 1 d . U . A -1
C9 C 0.0355(13) 0.3995(7) 0.2405(9) 0.021(3) Uani 0.5 1 d . U . A -1
C10 C 0.0444(17) 0.3920(9) 0.4538(9) 0.025(3) Uani 0.5 1 d . U . A -1
H10 H -0.042208 0.413003 0.450052 0.030 Uiso 0.5 1 calc R . . A -1
C11 C 0.2652(15) 0.3670(7) 0.3919(9) 0.024(3) Uani 0.5 1 d . U . A -1
H11 H 0.324769 0.369694 0.347334 0.029 Uiso 0.5 1 calc R . . A -1
C12 C 0.3080(15) 0.3351(9) 0.4648(9) 0.027(3) Uani 0.5 1 d . U . A -1
H12 H 0.396042 0.315736 0.469436 0.032 Uiso 0.5 1 calc R . . A -1
C13 C -0.2230(15) 0.4117(8) 0.0739(9) 0.026(3) Uani 0.5 1 d . U . A -1
H13 H -0.278372 0.441543 0.103715 0.032 Uiso 0.5 1 d R . . A -1
C14 C -0.2754(15) 0.3808(8) 0.0054(9) 0.026(3) Uani 0.5 1 d . U . A -1
H14 H -0.364024 0.392774 -0.012922 0.031 Uiso 0.5 1 d R . . A -1
C15 C -0.022(2) 0.4338(12) 0.1731(12) 0.027(5) Uani 0.5 1 d . U . A -1
C16 C -0.0848(19) 0.3990(10) 0.1004(12) 0.018(3) Uani 0.5 1 d . U . A -1
C17 C -0.0605(19) 0.3233(11) -0.0188(9) 0.026(4) Uani 0.5 1 d . U . A -1
H17 H -0.005144 0.296385 -0.052373 0.031 Uiso 0.5 1 d R . . A -1
C18 C -0.0051(16) 0.3552(9) 0.0508(8) 0.021(3) Uani 0.5 1 d . U . A -1
H18 H 0.087213 0.347449 0.065829 0.025 Uiso 0.5 1 d R . . A -1


_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 2.506(5) 6_566 ?
Eu1 O1 2.506(5) 5_566 ?
Eu1 O4 2.410(5) 2_556 ?
Eu1 O4 2.410(5) . ?
Eu1 O6 2.334(5) 2_556 ?
Eu1 O6 2.335(5) . ?
Eu1 O7 2.392(4) 7_556 ?
Eu1 O7 2.392(4) 8_455 ?
Eu1 C2 2.866(10) 5_566 ?
Eu1 C7 3.244(6) 7_556 ?
Eu1 C7 3.244(6) 8_455 ?
O1 C2 1.266(6) . ?
Cl3 C9 1.761(14) . ?
O4 H4A 0.8742 . ?
O4 H4B 0.8739 . ?
O6 C7 1.260(9) . ?
O7 C7 1.251(8) . ?
C1 C2 1.476(13) . ?
C1 C5 1.397(8) 2 ?
C1 C5 1.397(8) . ?
C3 C5 1.40(2) . ?
C3 C8 1.53(2) . ?
C3 C9 1.39(2) . ?
C4 C6 1.289(18) . ?
C4 C7 1.499(9) . ?
C4 C12 1.535(17) . ?
C4 C14 1.346(16) 2 ?
C4 C17 1.447(19) 2 ?
C5 H5 0.9801 . ?
C5 C15 1.41(2) 2 ?
C6 H6 0.9300 . ?
C6 C10 1.39(2) . ?
C8 C10 1.41(2) . ?
C8 C11 1.35(2) . ?
C9 C15 1.39(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.39(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9299 . ?
C13 C14 1.36(2) . ?
C13 C16 1.41(2) . ?
C14 H14 0.9299 . ?
C15 C16 1.48(2) . ?
C16 C18 1.41(3) . ?
C17 H17 0.9298 . ?
C17 C18 1.39(2) . ?
C18 H18 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
O1 Eu1 O1 52.36(19) 5_566 6_566 ?
O1 Eu1 C2 26.18(10) 5_566 5_566 ?
O1 Eu1 C2 26.18(10) 6_566 5_566 ?
O1 Eu1 C7 128.01(15) 5_566 8_455 ?
O1 Eu1 C7 75.65(15) 5_566 7_556 ?
O1 Eu1 C7 75.65(15) 6_566 8_455 ?
O1 Eu1 C7 128.01(15) 6_566 7_556 ?
O4 Eu1 O1 145.91(17) 2_556 5_566 ?
O4 Eu1 O1 129.49(16) . 5_566 ?
O4 Eu1 O1 145.91(17) . 6_566 ?
O4 Eu1 O1 129.49(16) 2_556 6_566 ?
O4 Eu1 O4 70.7(3) 2_556 . ?
O4 Eu1 C2 144.66(13) 2_556 5_566 ?
O4 Eu1 C2 144.66(13) . 5_566 ?
O4 Eu1 C7 67.16(16) . 7_556 ?
O4 Eu1 C7 67.16(16) 2_556 8_455 ?
O4 Eu1 C7 93.07(17) . 8_455 ?
O4 Eu1 C7 93.07(17) 2_556 7_556 ?
O6 Eu1 O1 72.72(17) . 5_566 ?
O6 Eu1 O1 77.03(17) . 6_566 ?
O6 Eu1 O1 72.72(17) 2_556 6_566 ?
O6 Eu1 O1 77.03(17) 2_556 5_566 ?
O6 Eu1 O4 73.04(18) 2_556 2_556 ?
O6 Eu1 O4 73.04(18) . . ?
O6 Eu1 O4 139.97(18) . 2_556 ?
O6 Eu1 O4 139.97(18) 2_556 . ?
O6 Eu1 O6 146.2(3) 2_556 . ?
O6 Eu1 O7 106.70(17) . 7_556 ?
O6 Eu1 O7 81.61(17) . 8_455 ?
O6 Eu1 O7 81.61(17) 2_556 7_556 ?
O6 Eu1 O7 106.70(17) 2_556 8_455 ?
O6 Eu1 C2 73.11(13) 2_556 5_566 ?
O6 Eu1 C2 73.11(13) . 5_566 ?
O6 Eu1 C7 88.01(17) 2_556 8_455 ?
O6 Eu1 C7 88.01(17) . 7_556 ?
O6 Eu1 C7 98.85(17) . 8_455 ?
O6 Eu1 C7 98.85(17) 2_556 7_556 ?
O7 Eu1 O1 128.64(17) 7_556 6_566 ?
O7 Eu1 O1 79.19(17) 7_556 5_566 ?
O7 Eu1 O1 128.64(17) 8_455 5_566 ?
O7 Eu1 O1 79.19(17) 8_455 6_566 ?
O7 Eu1 O4 80.65(17) 7_556 2_556 ?
O7 Eu1 O4 76.42(17) 8_455 2_556 ?
O7 Eu1 O4 80.65(17) 8_455 . ?
O7 Eu1 O4 76.43(17) 7_556 . ?
O7 Eu1 O7 151.8(3) 8_455 7_556 ?
O7 Eu1 C2 104.09(14) 7_556 5_566 ?
O7 Eu1 C2 104.09(14) 8_455 5_566 ?
O7 Eu1 C7 18.91(16) 7_556 7_556 ?
O7 Eu1 C7 147.80(17) 7_556 8_455 ?
O7 Eu1 C7 147.80(17) 8_455 7_556 ?
O7 Eu1 C7 18.91(16) 8_455 8_455 ?
C2 Eu1 C7 101.83(12) 5_566 7_556 ?
C2 Eu1 C7 101.83(12) 5_566 8_455 ?
C7 Eu1 C7 156.3(2) 8_455 7_556 ?
C2 O1 Eu1 93.0(5) . 5_566 ?
Eu1 O4 H4A 110.8 . . ?
Eu1 O4 H4B 110.3 . . ?
H4A O4 H4B 103.3 . . ?
C7 O6 Eu1 172.9(5) . . ?
C7 O7 Eu1 122.8(4) . 7_556 ?
C5 C1 C2 120.9(4) 2 . ?
C5 C1 C2 120.9(4) . . ?
C5 C1 C5 118.2(9) . 2 ?
O1 C2 Eu1 60.8(4) . 5_566 ?
O1 C2 Eu1 60.8(4) 2 5_566 ?
O1 C2 O1 121.7(9) . 2 ?
O1 C2 C1 119.2(4) . . ?
O1 C2 C1 119.2(4) 2 . ?
C1 C2 Eu1 180.0 . 5_566 ?
C5 C3 C8 120.1(16) . . ?
C9 C3 C5 117.6(15) . . ?
C9 C3 C8 122.0(19) . . ?
C6 C4 C7 128.2(10) . . ?
C6 C4 C12 117.5(10) . . ?
C6 C4 C14 95.9(12) . 2 ?
C6 C4 C17 30.2(8) . 2 ?
C7 C4 C12 114.2(8) . . ?
C14 C4 C7 124.8(8) 2 . ?
C14 C4 C12 42.8(9) 2 . ?
C14 C4 C17 117.6(11) 2 2 ?
C17 C4 C7 116.5(9) 2 . ?
C17 C4 C12 118.2(9) 2 . ?
C1 C5 C3 121.4(10) . . ?
C1 C5 H5 118.8 . . ?
C1 C5 C15 120.3(10) . 2 ?
C3 C5 H5 118.8 . . ?
C3 C5 C15 24.5(9) . 2 ?
C15 C5 H5 118.7 2 . ?
C4 C6 H6 118.2 . . ?
C4 C6 C10 123.5(15) . . ?
C10 C6 H6 118.2 . . ?
O6 C7 Eu1 86.2(4) . 7_556 ?
O6 C7 C4 118.2(6) . . ?
O7 C7 Eu1 38.3(3) . 7_556 ?
O7 C7 O6 123.5(6) . . ?
O7 C7 C4 118.3(6) . . ?
C4 C7 Eu1 153.9(5) . 7_556 ?
C10 C8 C3 113.7(16) . . ?
C11 C8 C3 124.5(16) . . ?
C11 C8 C10 121.7(15) . . ?
C3 C9 Cl3 117.9(13) . . ?
C3 C9 C15 122.7(12) . . ?
C15 C9 Cl3 119.4(13) . . ?
C6 C10 C8 119.3(15) . . ?
C6 C10 H10 120.4 . . ?
C8 C10 H10 120.4 . . ?
C8 C11 H11 120.4 . . ?
C8 C11 C12 119.2(15) . . ?
C12 C11 H11 120.4 . . ?
C4 C12 H12 120.7 . . ?
C11 C12 C4 118.6(12) . . ?
C11 C12 H12 120.7 . . ?
C14 C13 H13 119.8 . . ?
C14 C13 C16 120.6(14) . . ?
C16 C13 H13 119.6 . . ?
C13 C14 H14 118.6 . . ?
C9 C15 C16 123.9(19) . . ?
C13 C16 C15 122.3(17) . . ?
C18 C16 C13 116.7(15) . . ?
C18 C16 C15 120.8(17) . . ?
C18 C17 H17 120.9 . . ?
C16 C18 H18 118.4 . . ?
C17 C18 C16 122.0(16) . . ?
C17 C18 H18 119.6 . . ?

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 C2 O1 0.000(1) 5_566 . . 2 ?
Eu1 O1 C2 C1 180.000(1) 5_566 . . . ?
Eu1 O7 C7 O6 -15.4(9) 7_556 . . . ?
Eu1 O7 C7 C4 164.4(5) 7_556 . . . ?
Cl3 C9 C15 C16 7(2) . . . . ?
C2 C1 C5 C3 -168.3(10) . . . . ?
C2 C1 C5 C15 163.1(11) . . . 2 ?
C3 C8 C10 C6 -180.0(17) . . . . ?
C3 C8 C11 C12 177.4(17) . . . . ?
C3 C9 C15 C16 -171.8(19) . . . . ?
C4 C6 C10 C8 5(3) . . . . ?
C5 C1 C2 O1 -160.7(5) . . . . ?
C5 C1 C2 O1 19.3(5) 2 . . . ?
C5 C1 C2 O1 19.3(5) . . . 2 ?
C5 C1 C2 O1 -160.7(5) 2 . . 2 ?
C5 C1 C5 C3 11.7(10) 2 . . . ?
C5 C1 C5 C15 -16.9(11) 2 . . 2 ?
C5 C3 C8 C10 66(2) . . . . ?
C5 C3 C8 C11 -110(2) . . . . ?
C5 C3 C9 Cl3 -174.8(11) . . . . ?
C5 C3 C9 C15 4(2) . . . . ?
C6 C4 C7 Eu1 -137.8(14) . . . 7_556 ?
C6 C4 C7 O6 19.7(16) . . . . ?
C6 C4 C7 O7 -160.1(13) . . . . ?
C6 C4 C12 C11 2(2) . . . . ?
C7 C4 C6 C10 178.6(13) . . . . ?
C7 C4 C12 C11 179.5(11) . . . . ?
C8 C3 C5 C1 -179.3(12) . . . . ?
C8 C3 C5 C15 -84(3) . . . 2 ?
C8 C3 C9 Cl3 -1(2) . . . . ?
C8 C3 C9 C15 177.7(18) . . . . ?
C8 C11 C12 C4 -1(2) . . . . ?
C9 C3 C5 C1 -5(2) . . . . ?
C9 C3 C5 C15 90(3) . . . 2 ?
C9 C3 C8 C10 -108(2) . . . . ?
C9 C3 C8 C11 76(2) . . . . ?
C9 C15 C16 C13 123(2) . . . . ?
C9 C15 C16 C18 -61(3) . . . . ?
C10 C8 C11 C12 1(3) . . . . ?
C11 C8 C10 C6 -3(3) . . . . ?
C12 C4 C6 C10 -5(2) . . . . ?
C12 C4 C7 Eu1 45.4(15) . . . 7_556 ?
C12 C4 C7 O6 -157.1(9) . . . . ?
C12 C4 C7 O7 23.1(11) . . . . ?
C13 C16 C18 C17 -3(3) . . . . ?
C14 C4 C6 C10 34(2) 2 . . . ?
C14 C4 C7 Eu1 -2.7(18) 2 . . 7_556 ?
C14 C4 C7 O6 154.8(11) 2 . . . ?
C14 C4 C7 O7 -25.0(14) 2 . . . ?
C14 C4 C12 C11 -64.7(15) 2 . . . ?
C14 C13 C16 C15 177.7(17) . . . . ?
C14 C13 C16 C18 2(3) . . . . ?
C15 C16 C18 C17 -178.4(17) . . . . ?
C17 C4 C6 C10 -104(3) 2 . . . ?
C17 C4 C7 Eu1 -171.1(11) 2 . . 7_556 ?
C17 C4 C7 O6 -13.6(13) 2 . . . ?
C17 C4 C7 O7 166.6(10) 2 . . . ?
C17 C4 C12 C11 36.6(19) 2 . . . ?

_platon_squeeze_details          ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.002 678 190 ' '
2 0.500 0.500 0.070 678 190 ' '

_platon_squeeze_void_probe_radius 1.20
_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 4.713
_oxdiff_exptl_absorpt_empirical_full_min 0.234
####################################################################### 
# 
# 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_UPC-38-CH3
_database_code_depnum_ccdc_archive 'CCDC 1951708'
loop_
_audit_author_name
_audit_author_address
'wang yutong'
;China University of Petroleum(East China)
China
;
_audit_update_record             
;
2019-09-05 deposited with the CCDC.	2019-12-06 downloaded from the CCDC.
;
_audit_creation_date             2018-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H8.5 Eu0.5 O4, C3 H7 N O'
_chemical_formula_sum            'C14 H15.50 Eu0.50 N O5'
_chemical_formula_weight         353.75
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Eu'
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/c 1'
_space_group_name_Hall           '-I 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   9.56544(20)
_cell_length_b                   18.1811(4)
_cell_length_c                   16.2291(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.8608(17)
_cell_angle_gamma                90
_cell_volume                     2818.88(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4783
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      70.5890
_cell_measurement_theta_min      4.8570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    16.450
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_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  0.0270
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6529
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.616
_diffrn_reflns_theta_min         3.653
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -22.00  69.00   1.00    2.59    --    0.00  57.00-180.00   91
  2  ω    -69.00  22.00   1.00    2.59    --    0.00 -57.00 -30.00   91
  3  ω    -17.00  86.00   1.00   10.37    --   54.00 -77.00  90.00  103
  4  ω     32.00 123.00   1.00   10.37    --   54.00  57.00-150.00   91
  5  ω     23.00 112.00   1.00   10.37    --   54.00-125.00  90.00   89
  6  ω     23.00 112.00   1.00   10.37    --   54.00-125.00-180.00   89
  7  ω     22.00 120.00   1.00   10.37    --   54.00  77.00 -90.00   98
  8  ω     59.00 150.00   1.00   10.37    --  108.00 178.00 -30.00   91
  9  ω     67.00 111.00   1.00   10.37    --  108.00-111.00 -30.00   44
 10  ω     35.00 147.00   1.00   10.37    --  108.00 -25.00-120.00  112
 11  ω     65.00 118.00   1.00   10.37    --  108.00 -63.00  90.00   53
 12  ω    112.00 139.00   1.00   10.37    --  108.00 111.00-180.00   27
 13  ω    128.00 176.00   1.00   10.37    --  108.00 111.00 150.00   48
 14  ω     50.00 105.00   1.00   10.37    --  108.00-111.00 120.00   55
 15  ω     96.00 178.00   1.00   10.37    --  108.00  38.00 -90.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1149921000
_diffrn_orient_matrix_UB_12      -0.0586445000
_diffrn_orient_matrix_UB_13      -0.0137448000
_diffrn_orient_matrix_UB_21      -0.1130322000
_diffrn_orient_matrix_UB_22      0.0599284000
_diffrn_orient_matrix_UB_23      0.0056517000
_diffrn_orient_matrix_UB_31      0.0019699000
_diffrn_orient_matrix_UB_32      0.0122108000
_diffrn_orient_matrix_UB_33      -0.0938752000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2615
_reflns_number_total             2659
_reflns_odcompleteness_completeness 100.00
_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.
 
 _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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         2.042
_refine_diff_density_min         -1.012
_refine_diff_density_rms         0.166
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2659
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0570
_refine_ls_restrained_S_all      1.151
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0286P)²+91.0087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1411
_refine_ls_wR_factor_ref         0.1415
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Fixed Sof: H13A(0.5) H13B(0.5) H13C(0.5)
3.a Rotating group:
 O4(H4A,H4B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C14(H14), C5(H5), C6(H6), C4(H4)
3.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.0000 0.77576(3) 0.2500 0.01104(18) Uani 1 2 d S T P . .
O2 O 0.3904(7) 0.6949(4) 0.3744(4) 0.0388(16) Uani 1 1 d . . . . .
O1 O 0.1836(6) 0.7402(4) 0.3402(4) 0.048(2) Uani 1 1 d . . . . .
O4 O 0.1373(6) 0.8838(3) 0.2921(4) 0.0293(13) Uani 1 1 d . . . . .
H4A H 0.1359 0.9171 0.2525 0.044 Uiso 1 1 d GR . . . .
H4B H 0.2255 0.8717 0.3037 0.044 Uiso 1 1 d GR . . . .
O3 O -0.0803(6) 0.3482(3) 0.7969(4) 0.0308(14) Uani 1 1 d . . . . .
C8 C 0.0544(8) 0.5796(4) 0.6843(4) 0.0193(15) Uani 1 1 d . . . . .
C2 C 0.2124(8) 0.6783(4) 0.4682(4) 0.0181(15) Uani 1 1 d . . . . .
C3 C 0.2975(11) 0.6526(11) 0.5283(7) 0.095(7) Uani 1 1 d . . . . .
H3 H 0.3936 0.6556 0.5226 0.114 Uiso 1 1 calc R . . . .
C12 C 0.0000 0.3821(6) 0.7500 0.024(2) Uani 1 2 d S T P . .
C7 C 0.1101(8) 0.6169(4) 0.6116(5) 0.0192(15) Uani 1 1 d . . . . .
C9 C 0.0000 0.6191(6) 0.7500 0.018(2) Uani 1 2 d S T P . .
N9 N 0.3483(10) 0.4200(6) 0.4138(6) 0.054(2) Uani 1 1 d . . . . .
C11 C 0.0000 0.4649(6) 0.7500 0.017(2) Uani 1 2 d S T P . .
C1 C 0.2651(8) 0.7066(4) 0.3886(4) 0.0183(15) Uani 1 1 d . . . . .
C10 C 0.0553(8) 0.5026(4) 0.6855(5) 0.0194(15) Uani 1 1 d . . . . .
H10 H 0.0934 0.4768 0.6425 0.023 Uiso 1 1 calc R . . . .
C14 C 0.3543(15) 0.4864(7) 0.3745(8) 0.061(3) Uani 1 1 d . . . . .
H14 H 0.3466 0.5307 0.4026 0.073 Uiso 1 1 calc R . . . .
C13 C 0.0000 0.7012(6) 0.7500 0.028(3) Uani 1 2 d S T P . .
H13A H 0.0789 0.7188 0.7214 0.042 Uiso 0.5 1 calc GR . . A -1
H13B H 0.0061 0.7188 0.8058 0.042 Uiso 0.5 1 calc GR . . A -1
H13C H -0.0849 0.7188 0.7228 0.042 Uiso 0.5 1 calc GR . . A -1
C15 C 0.3528(11) 0.3543(6) 0.3676(9) 0.060(3) Uani 1 1 d . . . . .
H15A H 0.2737 0.3525 0.3288 0.091 Uiso 1 1 calc GR . . . .
H15B H 0.3502 0.3128 0.4041 0.091 Uiso 1 1 calc GR . . . .
H15C H 0.4376 0.3530 0.3383 0.091 Uiso 1 1 calc GR . . . .
C5 C 0.0764(11) 0.6763(11) 0.4813(9) 0.104(7) Uani 1 1 d . . . . .
H5 H 0.0131 0.6963 0.4421 0.125 Uiso 1 1 calc R . . . .
C6 C 0.0266(11) 0.6451(12) 0.5521(9) 0.116(8) Uani 1 1 d . . . . .
H6 H -0.0696 0.6440 0.5582 0.140 Uiso 1 1 calc R . . . .
C4 C 0.2484(11) 0.6213(11) 0.6000(7) 0.103(7) Uani 1 1 d . . . . .
H4 H 0.3120 0.6033 0.6402 0.124 Uiso 1 1 calc R . . . .
O5 O 0.3715(17) 0.4840(8) 0.2957(12) 0.151(7) Uani 1 1 d . . . . .
C16 C 0.3604(19) 0.4312(12) 0.5240(13) 0.147(11) Uani 1 1 d . . . . .
H16A H 0.2790 0.4566 0.5414 0.221 Uiso 1 1 calc GR . . . .
H16B H 0.4426 0.4592 0.5396 0.221 Uiso 1 1 calc GR . . . .
H16C H 0.3662 0.3837 0.5499 0.221 Uiso 1 1 calc GR . . . .


_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 O2 2.381(5) 8_465 ?
Eu1 O2 2.381(5) 7_565 ?
Eu1 O1 2.322(6) . ?
Eu1 O1 2.322(6) 2 ?
Eu1 O4 2.441(5) 2 ?
Eu1 O4 2.441(5) . ?
Eu1 O3 2.511(5) 5_566 ?
Eu1 O3 2.511(5) 6_565 ?
Eu1 C12 2.871(10) 5_566 ?
O2 Eu1 2.381(5) 7_565 ?
O2 C1 1.251(9) . ?
O1 C1 1.240(9) . ?
O3 Eu1 2.510(5) 5_566 ?
O3 C12 1.268(7) . ?
C8 C7 1.484(10) . ?
C8 C9 1.407(9) . ?
C8 C10 1.399(11) . ?
C2 C3 1.324(12) . ?
C2 C1 1.500(10) . ?
C2 C5 1.329(13) . ?
C3 C4 1.398(14) . ?
C12 Eu1 2.871(10) 5_566 ?
C12 O3 1.268(7) 2_556 ?
C12 C11 1.505(14) . ?
C7 C6 1.325(13) . ?
C7 C4 1.348(12) . ?
C9 C8 1.407(9) 2_556 ?
C9 C13 1.493(15) . ?
N9 C14 1.368(15) . ?
N9 C15 1.412(15) . ?
N9 C16 1.80(2) . ?
C11 C10 1.380(9) 2_556 ?
C11 C10 1.380(9) . ?
C14 O5 1.30(2) . ?
C5 C6 1.387(14) . ?

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
O2 Eu1 O2 154.1(3) 8_465 7_565 ?
O2 Eu1 O4 80.6(2) 7_565 2 ?
O2 Eu1 O4 80.6(2) 8_465 . ?
O2 Eu1 O4 78.7(2) 7_565 . ?
O2 Eu1 O4 78.7(2) 8_465 2 ?
O2 Eu1 O3 77.9(2) 7_565 5_566 ?
O2 Eu1 O3 127.7(2) 8_465 5_566 ?
O2 Eu1 O3 127.7(2) 7_565 6_565 ?
O2 Eu1 O3 77.9(2) 8_465 6_565 ?
O2 Eu1 C12 102.94(16) 7_565 5_566 ?
O2 Eu1 C12 102.94(16) 8_465 5_566 ?
O1 Eu1 O2 104.2(2) 2 8_465 ?
O1 Eu1 O2 83.0(3) . 8_465 ?
O1 Eu1 O2 83.0(3) 2 7_565 ?
O1 Eu1 O2 104.2(2) . 7_565 ?
O1 Eu1 O1 147.7(4) . 2 ?
O1 Eu1 O4 141.2(2) . 2 ?
O1 Eu1 O4 141.3(2) 2 . ?
O1 Eu1 O4 70.6(2) . . ?
O1 Eu1 O4 70.6(2) 2 2 ?
O1 Eu1 O3 73.0(3) . 5_566 ?
O1 Eu1 O3 78.0(2) . 6_565 ?
O1 Eu1 O3 73.0(3) 2 6_565 ?
O1 Eu1 O3 78.0(2) 2 5_566 ?
O1 Eu1 C12 73.84(19) 2 5_566 ?
O1 Eu1 C12 73.84(19) . 5_566 ?
O4 Eu1 O4 72.9(3) . 2 ?
O4 Eu1 O3 143.7(2) 2 5_566 ?
O4 Eu1 O3 129.67(19) . 5_566 ?
O4 Eu1 O3 129.67(19) 2 6_565 ?
O4 Eu1 O3 143.7(2) . 6_565 ?
O4 Eu1 C12 143.56(13) 2 5_566 ?
O4 Eu1 C12 143.56(13) . 5_566 ?
O3 Eu1 O3 52.4(2) 5_566 6_565 ?
O3 Eu1 C12 26.18(12) 5_566 5_566 ?
O3 Eu1 C12 26.18(12) 6_565 5_566 ?
C1 O2 Eu1 125.8(5) . 7_565 ?
C1 O1 Eu1 165.6(6) . . ?
C12 O3 Eu1 93.0(5) . 5_566 ?
C9 C8 C7 122.1(7) . . ?
C10 C8 C7 117.7(6) . . ?
C10 C8 C9 120.2(7) . . ?
C3 C2 C1 122.3(7) . . ?
C3 C2 C5 116.4(8) . . ?
C5 C2 C1 121.4(7) . . ?
C2 C3 C4 122.5(9) . . ?
O3 C12 Eu1 60.8(5) . 5_566 ?
O3 C12 Eu1 60.8(5) 2_556 5_566 ?
O3 C12 O3 121.7(10) 2_556 . ?
O3 C12 C11 119.2(5) . . ?
O3 C12 C11 119.2(5) 2_556 . ?
C11 C12 Eu1 180.0 . 5_566 ?
C6 C7 C8 121.9(8) . . ?
C6 C7 C4 115.8(8) . . ?
C4 C7 C8 122.2(8) . . ?
C8 C9 C8 118.6(9) 2_556 . ?
C8 C9 C13 120.7(5) . . ?
C8 C9 C13 120.7(5) 2_556 . ?
C14 N9 C15 119.7(10) . . ?
C14 N9 C16 111.2(10) . . ?
C15 N9 C16 128.5(11) . . ?
C10 C11 C12 119.8(5) . . ?
C10 C11 C12 119.8(5) 2_556 . ?
C10 C11 C10 120.3(10) 2_556 . ?
O2 C1 C2 117.9(7) . . ?
O1 C1 O2 123.0(7) . . ?
O1 C1 C2 119.1(7) . . ?
C11 C10 C8 120.3(7) . . ?
O5 C14 N9 116.2(12) . . ?
C2 C5 C6 121.5(9) . . ?
C7 C6 C5 122.8(10) . . ?
C7 C4 C3 120.9(9) . . ?

_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 1.551
_oxdiff_exptl_absorpt_empirical_full_min 0.646
####################################################################### 
# 
# 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_UPC-38-F
_database_code_depnum_ccdc_archive 'CCDC 1951707'
loop_
_audit_author_name
_audit_author_address
'wang yutong'
;China University of Petroleum(East China)
China
;
_audit_update_record             
;
2019-09-05 deposited with the CCDC.	2019-12-06 downloaded from the CCDC.
;
_audit_creation_date             2018-11-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10.5 H7 Eu0.5 F0.5 O4, C3 H7 N O'
_chemical_formula_sum            'C13.50 H14 Eu0.50 F0.50 N O5'
_chemical_formula_weight         355.74
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Eu'
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'
F F 0.0727 0.0534 '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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/c 1'
_space_group_name_Hall           '-I 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   9.5953(3)
_cell_length_b                   18.5323(7)
_cell_length_c                   15.7144(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.776(3)
_cell_angle_gamma                90
_cell_volume                     2780.19(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5706
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      70.5230
_cell_measurement_theta_min      5.2190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    16.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_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  0.0600
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10320
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.604
_diffrn_reflns_theta_min         3.699
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  22.00   1.00    1.00    --    0.00 -57.00-150.00   91
  2  ω    -16.00  20.00   1.00    1.00    --    0.00  57.00-180.00   36
  3  ω     44.00 108.00   1.00    3.43    --   54.00-125.00-180.00   64
  4  ω    -15.00  74.00   1.00    3.43    --   54.00 -57.00 150.00   89
  5  ω     16.00  80.00   1.00    3.43    --   54.00 -38.00 -60.00   64
  6  ω     23.00 125.00   1.00    3.43    --   54.00  77.00 -60.00  102
  7  ω     92.00 135.00   1.00    3.43    --  108.00  50.00  60.00   43
  8  ω    126.00 156.00   1.00    3.43    --  108.00 111.00-180.00   30
  9  ω     40.00 131.00   1.00    3.43    --  108.00 -50.00 -90.00   91
 10  ω    100.00 175.00   1.00    3.43    --  108.00  63.00 -90.00   75
 11  ω     96.00 132.00   1.00    3.43    --  108.00 -63.00-180.00   36
 12  ω     43.00 130.00   1.00    3.43    --  108.00 -91.00 150.00   87
 13  ω     41.00  93.00   1.00    3.43    --  108.00 -63.00-180.00   52
 14  ω     58.00 133.00   1.00    3.43    --  108.00 178.00-180.00   75
 15  ω     22.00  52.00   1.00    1.00    --    0.00  57.00   0.00   30
 16  ω    -14.00  16.00   1.00    1.00    --    0.00  57.00   0.00   30
 17  ω     17.00  43.00   1.00    1.00    --    0.00  57.00  30.00   26
 18  ω     53.00  96.00   1.00    3.43    --   54.00-125.00  60.00   43
 19  ω     32.00  59.00   1.00    3.43    --   54.00  57.00 150.00   27
 20  ω     42.00  68.00   1.00    3.43    --   54.00-125.00 -90.00   26
 21  ω     76.00 121.00   1.00    3.43    --   54.00  57.00-150.00   45
 22  ω     43.00 114.00   1.00    3.43    --   54.00  57.00  90.00   71
 23  ω     98.00 123.00   1.00    3.43    --   54.00  57.00 150.00   25
 24  ω     31.00  56.00   1.00    3.43    --   54.00 -38.00-180.00   25
 25  ω    101.00 147.00   1.00    3.43    --  108.00 -25.00-180.00   46
 26  ω     97.00 155.00   1.00    3.43    --  108.00  63.00-180.00   58
 27  ω     34.00  79.00   1.00    3.43    --  108.00 -25.00-180.00   45
 28  ω     58.00  94.00   1.00    3.43    --  108.00 178.00  90.00   36
 29  ω     85.00 110.00   1.00    3.43    --  108.00  63.00 120.00   25
 30  ω    106.00 132.00   1.00    3.43    --  108.00 -63.00  60.00   26
 31  ω     65.00 115.00   1.00    3.43    --  108.00-111.00 150.00   50
 32  ω     47.00  74.00   1.00    3.43    --  108.00 -63.00  60.00   27
 33  ω     59.00 103.00   1.00    3.43    --  108.00-111.00 -30.00   44
 34  ω    130.00 156.00   1.00    3.43    --  108.00  63.00 120.00   26
 35  ω     60.00 113.00   1.00    3.43    --  108.00-111.00  60.00   53
 36  ω    120.00 146.00   1.00    3.43    --  108.00 178.00  90.00   26
 37  ω    134.00 160.00   1.00    3.43    --  108.00 111.00   0.00   26
 38  ω     90.00 133.00   1.00    3.43    --  108.00 -25.00  90.00   43
 39  ω     34.00  68.00   1.00    3.43    --  108.00 -25.00  90.00   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0629725000
_diffrn_orient_matrix_UB_12      -0.0703228000
_diffrn_orient_matrix_UB_13      -0.0395362000
_diffrn_orient_matrix_UB_21      0.1352471000
_diffrn_orient_matrix_UB_22      -0.0407846000
_diffrn_orient_matrix_UB_23      0.0318217000
_diffrn_orient_matrix_UB_31      -0.0613418000
_diffrn_orient_matrix_UB_32      -0.0175870000
_diffrn_orient_matrix_UB_33      0.0844640000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2546
_reflns_number_total             2648
_reflns_odcompleteness_completeness 100.00
_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.
 
 _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 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         3.844
_refine_diff_density_min         -0.844
_refine_diff_density_rms         0.154
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.281
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2648
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.281
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0485P)²+32.1978P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1378
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Rotating group:
 O4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C13(H13), C7(H7), C12(H12), C6(H6)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.0000 0.21972(2) 0.2500 0.01548(18) Uani 1 2 d S T P . .
O1 O 0.1146(5) 0.1865(3) 0.1283(3) 0.0261(10) Uani 1 1 d . . . . .
O4 O 0.1405(5) 0.1142(2) 0.2984(3) 0.0245(10) Uani 1 1 d . . . . .
H4A H 0.2297 0.1249 0.3041 0.037 Uiso 1 1 d GR . . . .
H4B H 0.1340 0.0807 0.2591 0.037 Uiso 1 1 d GR . . . .
F1 F 0.5000 0.1768(3) -0.2500 0.0366(15) Uani 1 2 d S T P . .
O2 O 0.3141(5) 0.2459(3) 0.1533(3) 0.0346(12) Uani 1 1 d . . . . .
O3 O -0.0770(5) 0.3416(2) 0.2980(3) 0.0259(10) Uani 1 1 d . . . . .
C8 C 0.4457(7) 0.0682(4) -0.1826(4) 0.0248(14) Uani 1 1 d . . . . .
C2 C 0.2866(7) 0.1714(3) 0.0315(4) 0.0236(14) Uani 1 1 d . . . . .
N1 N -0.1523(9) 0.0958(5) -0.1037(5) 0.056(2) Uani 1 1 d . . . . .
C1 C 0.2339(7) 0.2030(3) 0.1103(4) 0.0220(13) Uani 1 1 d . . . . .
C9 C 0.5000 0.1037(5) -0.2500 0.026(2) Uani 1 2 d S T P . .
C3 C 0.2085(9) 0.1207(5) -0.0165(5) 0.0365(18) Uani 1 1 d . . . . .
H3 H 0.1205 0.1078 -0.0014 0.044 Uiso 1 1 calc R . . . .
C10 C 0.0000 0.3744(5) 0.2500 0.0199(18) Uani 1 2 d S T P . .
C4 C 0.2588(9) 0.0884(5) -0.0871(5) 0.041(2) Uani 1 1 d . . . . .
H4 H 0.2049 0.0541 -0.1185 0.050 Uiso 1 1 calc R . . . .
C5 C 0.3895(8) 0.1072(4) -0.1108(4) 0.0251(14) Uani 1 1 d . . . . .
C13 C -0.1446(11) 0.0298(6) -0.1415(6) 0.051(2) Uani 1 1 d . . . . .
H13 H -0.1604 -0.0103 -0.1082 0.062 Uiso 1 1 calc R . . . .
C11 C 0.0000 0.4555(5) 0.2500 0.0235(19) Uani 1 2 d S T P . .
C7 C 0.4152(8) 0.1911(5) 0.0062(5) 0.0374(18) Uani 1 1 d . . . . .
H7 H 0.4681 0.2261 0.0371 0.045 Uiso 1 1 calc R . . . .
C12 C -0.0544(7) 0.4930(4) 0.3149(4) 0.0253(14) Uani 1 1 d . . . . .
H12 H -0.0921 0.4675 0.3581 0.030 Uiso 1 1 calc R . . . .
C6 C 0.4666(8) 0.1598(4) -0.0642(5) 0.0375(19) Uani 1 1 d . . . . .
H6 H 0.5531 0.1740 -0.0803 0.045 Uiso 1 1 calc R . . . .
C14 C -0.1417(15) 0.1599(7) -0.1555(8) 0.078(4) Uani 1 1 d . . . . .
H14A H -0.0448 0.1715 -0.1585 0.118 Uiso 1 1 calc GR . . . .
H14B H -0.1873 0.1995 -0.1303 0.118 Uiso 1 1 calc GR . . . .
H14C H -0.1860 0.1512 -0.2121 0.118 Uiso 1 1 calc GR . . . .
O5 O -0.1185(16) 0.0179(6) -0.2167(9) 0.126(4) Uani 1 1 d . . . . .
C15 C -0.1632(15) 0.1000(8) -0.0096(9) 0.082(4) Uiso 1 1 d . . . . .
H15A H -0.2590 0.1082 0.0003 0.123 Uiso 1 1 calc GR . . . .
H15B H -0.1063 0.1390 0.0143 0.123 Uiso 1 1 calc GR . . . .
H15C H -0.1313 0.0555 0.0168 0.123 Uiso 1 1 calc GR . . . .


_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 2.380(4) 2 ?
Eu1 O1 2.380(4) . ?
Eu1 O4 2.452(5) 2 ?
Eu1 O4 2.452(5) . ?
Eu1 O2 2.313(5) 8_455 ?
Eu1 O2 2.313(5) 7 ?
Eu1 O3 2.516(4) 2 ?
Eu1 O3 2.516(4) . ?
Eu1 C10 2.866(9) . ?
O1 C1 1.244(8) . ?
F1 C9 1.355(10) . ?
O2 Eu1 2.313(5) 7 ?
O2 C1 1.255(9) . ?
O3 C10 1.264(6) . ?
C8 C9 1.392(8) . ?
C8 C5 1.487(9) . ?
C8 C12 1.393(9) 3_544 ?
C2 C1 1.503(8) . ?
C2 C3 1.380(10) . ?
C2 C7 1.382(10) . ?
N1 C13 1.366(13) . ?
N1 C14 1.449(15) . ?
N1 C15 1.494(15) . ?
C9 C8 1.392(8) 2_654 ?
C3 C4 1.388(10) . ?
C10 O3 1.264(6) 2 ?
C10 C11 1.502(12) . ?
C4 C5 1.388(10) . ?
C5 C6 1.388(10) . ?
C13 O5 1.251(15) . ?
C11 C12 1.381(8) 2 ?
C11 C12 1.381(8) . ?
C7 C6 1.383(10) . ?
C12 C8 1.393(9) 3_455 ?

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 O1 150.1(2) 2 . ?
O1 Eu1 O4 80.14(15) . 2 ?
O1 Eu1 O4 76.07(16) 2 2 ?
O1 Eu1 O4 76.07(16) . . ?
O1 Eu1 O4 80.14(15) 2 . ?
O1 Eu1 O3 79.49(15) . 2 ?
O1 Eu1 O3 79.49(15) 2 . ?
O1 Eu1 O3 130.26(15) . . ?
O1 Eu1 O3 130.26(15) 2 2 ?
O1 Eu1 C10 104.97(11) . . ?
O1 Eu1 C10 104.97(11) 2 . ?
O4 Eu1 O4 74.2(2) . 2 ?
O4 Eu1 O3 129.82(15) . 2 ?
O4 Eu1 O3 142.35(16) 2 2 ?
O4 Eu1 O3 142.35(16) . . ?
O4 Eu1 O3 129.82(15) 2 . ?
O4 Eu1 C10 142.89(11) 2 . ?
O4 Eu1 C10 142.89(11) . . ?
O2 Eu1 O1 86.07(19) 7 2 ?
O2 Eu1 O1 102.17(17) 7 . ?
O2 Eu1 O1 86.07(19) 8_455 . ?
O2 Eu1 O1 102.17(17) 8_455 2 ?
O2 Eu1 O4 141.89(19) 7 2 ?
O2 Eu1 O4 69.67(18) 8_455 2 ?
O2 Eu1 O4 69.67(18) 7 . ?
O2 Eu1 O4 141.89(19) 8_455 . ?
O2 Eu1 O2 148.0(3) 7 8_455 ?
O2 Eu1 O3 73.71(19) 8_455 . ?
O2 Eu1 O3 77.63(17) 8_455 2 ?
O2 Eu1 O3 73.71(19) 7 2 ?
O2 Eu1 O3 77.63(17) 7 . ?
O2 Eu1 C10 74.01(14) 8_455 . ?
O2 Eu1 C10 74.01(14) 7 . ?
O3 Eu1 O3 52.26(19) 2 . ?
O3 Eu1 C10 26.13(10) 2 . ?
O3 Eu1 C10 26.13(10) . . ?
C1 O1 Eu1 129.0(4) . . ?
C1 O2 Eu1 156.7(5) . 7 ?
C10 O3 Eu1 92.6(4) . . ?
C9 C8 C5 122.6(6) . . ?
C9 C8 C12 116.8(6) . 3_544 ?
C12 C8 C5 120.6(6) 3_544 . ?
C3 C2 C1 120.5(6) . . ?
C3 C2 C7 118.3(6) . . ?
C7 C2 C1 121.3(6) . . ?
C13 N1 C14 118.7(8) . . ?
C13 N1 C15 119.3(10) . . ?
C14 N1 C15 121.9(10) . . ?
O1 C1 O2 124.2(6) . . ?
O1 C1 C2 119.1(6) . . ?
O2 C1 C2 116.8(6) . . ?
F1 C9 C8 118.2(4) . . ?
F1 C9 C8 118.2(4) . 2_654 ?
C8 C9 C8 123.6(9) . 2_654 ?
C2 C3 C4 121.1(7) . . ?
O3 C10 Eu1 61.3(4) . . ?
O3 C10 Eu1 61.3(4) 2 . ?
O3 C10 O3 122.6(8) . 2 ?
O3 C10 C11 118.7(4) . . ?
O3 C10 C11 118.7(4) 2 . ?
C11 C10 Eu1 180.0 . . ?
C3 C4 C5 120.2(7) . . ?
C4 C5 C8 119.2(6) . . ?
C6 C5 C8 121.9(6) . . ?
C6 C5 C4 118.9(6) . . ?
O5 C13 N1 126.4(11) . . ?
C12 C11 C10 120.3(4) 2 . ?
C12 C11 C10 120.3(4) . . ?
C12 C11 C12 119.4(8) 2 . ?
C2 C7 C6 121.4(7) . . ?
C11 C12 C8 121.7(6) . 3_455 ?
C5 C6 C7 120.1(7) . . ?

_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 2.946
_oxdiff_exptl_absorpt_empirical_full_min 0.592
####################################################################### 
# 
# 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_UPC-38-NH2
_database_code_depnum_ccdc_archive 'CCDC 1951709'
loop_
_audit_author_name
_audit_author_address
'wang yutong'
;China University of Petroleum(East China)
China
;
_audit_update_record             
;
2019-09-05 deposited with the CCDC.	2019-12-06 downloaded from the CCDC.
;
_audit_creation_date             2019-09-04
_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         'C10.5 H8 Eu0.5 N0.5 O4, C3 H7 N O'
_chemical_formula_sum            'C13.50 H15 Eu0.50 N1.50 O5'
_chemical_formula_weight         354.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Eu'
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/c 1'
_space_group_name_Hall           '-I 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   9.6351(3)
_cell_length_b                   18.2081(5)
_cell_length_c                   16.2735(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.405(3)
_cell_angle_gamma                90
_cell_volume                     2852.47(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2973
_cell_measurement_temperature    150
_cell_measurement_theta_max      70.1500
_cell_measurement_theta_min      4.8630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    16.267
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_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  0.0320
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5305
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.449
_diffrn_reflns_theta_min         3.645
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  22.00   1.00    3.50    --    0.00 -57.00   0.00   91
  2  ω    -20.00   6.00   1.00    3.50    --    0.00  57.00 -30.00   26
  3  ω     21.00  50.00   1.00    3.50    --    0.00  57.00 -30.00   29
  4  ω     98.00 123.00   1.00   14.02    --   53.47  57.00  30.00   25
  5  ω     28.00 110.00   1.00   14.02    --   53.47-125.00-180.00   82
  6  ω    -15.00  73.00   1.00   14.02    --   53.47 -57.00-120.00   88
  7  ω     43.00 123.00   1.00   14.02    --   53.47  57.00   0.00   80
  8  ω     93.00 152.00   1.00   14.02    --  106.95  63.00 -30.00   59
  9  ω    105.00 169.00   1.00   14.02    --  106.95 111.00-120.00   64
 10  ω     38.00  67.00   1.00   14.02    --  106.95-111.00  60.00   29
 11  ω     34.00 134.00   1.00   14.02    --  106.95 -38.00  90.00  100
 12  ω    140.00 174.00   1.00   14.02    --  106.95 111.00-150.00   34
 13  ω     44.00 123.00   1.00   14.02    --  106.95 -50.00-150.00   79
 14  ω    100.00 177.00   1.00   14.02    --  106.95 111.00-180.00   77
 15  ω     37.00 106.00   1.00   14.02    --  106.95-111.00 -90.00   69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0264752000
_diffrn_orient_matrix_UB_12      -0.0072752000
_diffrn_orient_matrix_UB_13      0.0936515000
_diffrn_orient_matrix_UB_21      -0.1410288000
_diffrn_orient_matrix_UB_22      -0.0390862000
_diffrn_orient_matrix_UB_23      0.0066732000
_diffrn_orient_matrix_UB_31      0.0710938000
_diffrn_orient_matrix_UB_32      -0.0746507000
_diffrn_orient_matrix_UB_33      -0.0125522000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2534
_reflns_number_total             2683
_reflns_odcompleteness_completeness 99.85
_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.
 
 _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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         3.472
_refine_diff_density_min         -1.007
_refine_diff_density_rms         0.168
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2683
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      1.067
_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)+(0.1287P)²+4.0354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1601
_refine_ls_wR_factor_ref         0.1642
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 O5-N2
 2.5 with sigma of 0.01
 C13-O5
 1.24 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
O5: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C13) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
4. Others
 Fixed Sof: H1C(0.5) H1D(0.5)
5.a Rotating group:
 O1(H1A,H1B), N1(H1C,H1D)
5.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C3(H3), C7(H7), C4(H4), C6(H6), C13(H13)
5.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 1.0000 0.77294(2) 0.7500 0.0291(2) Uani 1 2 d S T P . .
O3 O 0.6098(5) 0.6946(3) 0.6273(3) 0.0510(12) Uani 1 1 d . . . . .
O4 O 1.0788(5) 0.3501(2) 0.2031(3) 0.0421(10) Uani 1 1 d . . . . .
O2 O 0.8175(6) 0.7388(4) 0.6595(4) 0.0558(14) Uani 1 1 d . . . . .
O1 O 1.1362(5) 0.8818(3) 0.7921(4) 0.0523(12) Uani 1 1 d . . . . .
H1A H 1.1287 0.9167 0.7544 0.078 Uiso 1 1 d GR . . . .
H1B H 1.2251 0.8707 0.7993 0.078 Uiso 1 1 d GR . . . .
C8 C 0.9418(8) 0.5809(4) 0.3155(4) 0.0433(14) Uani 1 1 d . . . . .
N1 N 1.0000 0.6961(5) 0.2500 0.070(3) Uani 1 2 d S T P . .
H1C H 1.0209 0.7246 0.1989 0.084 Uiso 0.5 1 d GR . . . .
H1D H 0.9140 0.7247 0.2629 0.084 Uiso 0.5 1 d GR . . . .
C12 C 1.0000 0.3839(5) 0.2500 0.0340(17) Uani 1 2 d S T P . .
C5 C 0.8850(8) 0.6191(4) 0.3870(4) 0.0416(14) Uani 1 1 d . . . . .
C10 C 0.9401(7) 0.5049(4) 0.3137(4) 0.0401(13) Uani 1 1 d . . . . .
H10 H 0.8985 0.4793 0.3556 0.048 Uiso 1 1 calc R . . . .
C9 C 1.0000 0.6194(5) 0.2500 0.045(2) Uani 1 2 d S T P . .
C2 C 0.7853(7) 0.6781(4) 0.5326(4) 0.0382(13) Uani 1 1 d . . . . .
C11 C 1.0000 0.4658(5) 0.2500 0.0378(18) Uani 1 2 d S T P . .
N2 N 1.3440(11) 0.5822(8) 0.4075(7) 0.100(3) Uani 1 1 d D . . . .
C1 C 0.7344(7) 0.7061(4) 0.6117(4) 0.0374(13) Uani 1 1 d . . . . .
C3 C 0.6994(9) 0.6446(8) 0.4753(6) 0.085(4) Uani 1 1 d . . . . .
H3 H 0.6050 0.6419 0.4846 0.102 Uiso 1 1 calc R . . . .
C7 C 0.9218(9) 0.6857(8) 0.5141(6) 0.087(4) Uani 1 1 d . . . . .
H7 H 0.9830 0.7102 0.5504 0.105 Uiso 1 1 calc R . . . .
C4 C 0.7479(10) 0.6147(8) 0.4043(6) 0.089(4) Uani 1 1 d . . . . .
H4 H 0.6862 0.5912 0.3675 0.107 Uiso 1 1 calc R . . . .
C6 C 0.9696(9) 0.6568(8) 0.4411(6) 0.088(4) Uani 1 1 d . . . . .
H6 H 1.0622 0.6636 0.4290 0.105 Uiso 1 1 calc R . . . .
C14 C 1.3510(16) 0.6487(11) 0.3620(13) 0.133(7) Uani 1 1 d . . . . .
H14A H 1.4046 0.6409 0.3143 0.200 Uiso 1 1 calc GR . . . .
H14B H 1.3944 0.6860 0.3959 0.200 Uiso 1 1 calc GR . . . .
H14C H 1.2589 0.6640 0.3451 0.200 Uiso 1 1 calc GR . . . .
C13 C 1.362(2) 0.5152(9) 0.353(2) 0.241(16) Uani 1 1 d D U . . .
H13 H 1.3524 0.4701 0.3785 0.289 Uiso 1 1 calc R . . . .
C15 C 1.328(2) 0.5828(17) 0.4962(13) 0.182(11) Uani 1 1 d . . . . .
H15A H 1.3662 0.6276 0.5188 0.272 Uiso 1 1 calc GR . . . .
H15B H 1.3769 0.5417 0.5206 0.272 Uiso 1 1 calc GR . . . .
H15C H 1.2316 0.5796 0.5077 0.272 Uiso 1 1 calc GR . . . .
O5 O 1.389(14) 0.512(4) 0.279(3) 1.30(15) Uiso 1 1 d D 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 O3 2.373(4) 7_666 ?
Eu1 O3 2.373(4) 8_565 ?
Eu1 O4 2.495(4) 6_566 ?
Eu1 O4 2.495(4) 5_766 ?
Eu1 O2 2.331(6) . ?
Eu1 O2 2.331(6) 2_756 ?
Eu1 O1 2.458(5) 2_756 ?
Eu1 O1 2.458(5) . ?
Eu1 C12 2.856(8) 5_766 ?
O3 Eu1 2.373(4) 7_666 ?
O3 C1 1.255(8) . ?
O4 Eu1 2.495(4) 5_766 ?
O4 C12 1.260(6) . ?
O2 C1 1.243(9) . ?
C8 C5 1.481(9) . ?
C8 C10 1.385(10) . ?
C8 C9 1.411(8) . ?
N1 C9 1.396(13) . ?
C12 Eu1 2.856(8) 5_766 ?
C12 O4 1.260(6) 2_755 ?
C12 C11 1.492(12) . ?
C5 C4 1.365(12) . ?
C5 C6 1.361(12) . ?
C10 C11 1.401(8) . ?
C9 C8 1.411(8) 2_755 ?
C2 C1 1.487(8) . ?
C2 C3 1.364(11) . ?
C2 C7 1.369(11) . ?
C11 C10 1.401(8) 2_755 ?
N2 C14 1.42(2) . ?
N2 C13 1.52(3) . ?
N2 C15 1.46(2) . ?
C3 C4 1.377(12) . ?
C7 C6 1.395(12) . ?
C13 O5 1.239(10) . ?

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 O3 151.1(3) 7_666 8_565 ?
O3 Eu1 O4 129.29(17) 8_565 5_766 ?
O3 Eu1 O4 79.30(17) 8_565 6_566 ?
O3 Eu1 O4 79.30(17) 7_666 5_766 ?
O3 Eu1 O4 129.29(17) 7_666 6_566 ?
O3 Eu1 O1 79.42(18) 7_666 . ?
O3 Eu1 O1 77.4(2) 8_565 . ?
O3 Eu1 O1 79.42(18) 8_565 2_756 ?
O3 Eu1 O1 77.4(2) 7_666 2_756 ?
O3 Eu1 C12 104.43(14) 8_565 5_766 ?
O3 Eu1 C12 104.43(14) 7_666 5_766 ?
O4 Eu1 O4 52.3(2) 6_566 5_766 ?
O4 Eu1 C12 26.13(10) 5_766 5_766 ?
O4 Eu1 C12 26.13(10) 6_566 5_766 ?
O2 Eu1 O3 83.4(2) 2_756 7_666 ?
O2 Eu1 O3 104.3(2) 2_756 8_565 ?
O2 Eu1 O3 104.3(2) . 7_666 ?
O2 Eu1 O3 83.4(2) . 8_565 ?
O2 Eu1 O4 73.9(2) 2_756 6_566 ?
O2 Eu1 O4 73.9(2) . 5_766 ?
O2 Eu1 O4 78.35(18) . 6_566 ?
O2 Eu1 O4 78.35(18) 2_756 5_766 ?
O2 Eu1 O2 149.0(3) . 2_756 ?
O2 Eu1 O1 140.5(2) . . ?
O2 Eu1 O1 70.1(2) . 2_756 ?
O2 Eu1 O1 140.5(2) 2_756 2_756 ?
O2 Eu1 O1 70.1(2) 2_756 . ?
O2 Eu1 C12 74.51(16) 2_756 5_766 ?
O2 Eu1 C12 74.51(16) . 5_766 ?
O1 Eu1 O4 143.54(18) . 5_766 ?
O1 Eu1 O4 130.04(16) 2_756 5_766 ?
O1 Eu1 O4 143.54(18) 2_756 6_566 ?
O1 Eu1 O4 130.04(16) . 6_566 ?
O1 Eu1 O1 72.6(2) . 2_756 ?
O1 Eu1 C12 143.72(12) 2_756 5_766 ?
O1 Eu1 C12 143.72(12) . 5_766 ?
C1 O3 Eu1 126.3(4) . 7_666 ?
C12 O4 Eu1 93.1(4) . 5_766 ?
C1 O2 Eu1 166.3(5) . . ?
C10 C8 C5 118.7(6) . . ?
C10 C8 C9 119.1(6) . . ?
C9 C8 C5 122.2(6) . . ?
O4 C12 Eu1 60.7(4) . 5_766 ?
O4 C12 Eu1 60.7(4) 2_755 5_766 ?
O4 C12 O4 121.5(8) . 2_755 ?
O4 C12 C11 119.3(4) . . ?
O4 C12 C11 119.3(4) 2_755 . ?
C11 C12 Eu1 180.0 . 5_766 ?
C4 C5 C8 121.9(7) . . ?
C6 C5 C8 121.0(7) . . ?
C6 C5 C4 117.1(7) . . ?
C8 C10 C11 121.1(6) . . ?
C8 C9 C8 120.4(8) . 2_755 ?
N1 C9 C8 119.8(4) . 2_755 ?
N1 C9 C8 119.8(4) . . ?
C3 C2 C1 122.1(6) . . ?
C3 C2 C7 117.2(7) . . ?
C7 C2 C1 120.7(6) . . ?
C10 C11 C12 120.5(4) 2_755 . ?
C10 C11 C12 120.5(4) . . ?
C10 C11 C10 119.0(8) . 2_755 ?
C14 N2 C13 111.6(15) . . ?
C14 N2 C15 121.2(18) . . ?
C15 N2 C13 127(2) . . ?
O3 C1 C2 118.1(6) . . ?
O2 C1 O3 123.4(6) . . ?
O2 C1 C2 118.5(6) . . ?
C2 C3 C4 122.2(8) . . ?
C2 C7 C6 120.2(8) . . ?
C5 C4 C3 121.0(8) . . ?
C5 C6 C7 122.1(8) . . ?
O5 C13 N2 129(3) . . ?

_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 1.944
_oxdiff_exptl_absorpt_empirical_full_min 0.458
