# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2017

####################################################################### 
# 
# 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_EtAYYbEr_293K
_database_code_depnum_ccdc_archive 'CCDC 1556102'
_audit_update_record             
;
2017-06-14 deposited with the CCDC.
2017-08-14 downloaded from the CCDC.
;
_audit_creation_date             2017-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H4 Er0.02 O8 Y0.91 Yb0.07, C2 H8 N'
_chemical_formula_sum            'C6 H12 Er0.02 N O8 Y0.91 Yb0.07'
_chemical_formula_weight         322.53
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 H12 N1 O8 Y0.95 Yb0.04 Er0.01'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Y Y -2.7962 3.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Yb Yb -0.3850 5.5486 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.657(3)
_cell_length_b                   8.652(3)
_cell_length_c                   9.708(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.42(3)
_cell_angle_gamma                90
_cell_volume                     546.1(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7001
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1180
_cell_measurement_theta_min      3.1470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.640
_exptl_absorpt_correction_T_max  0.449
_exptl_absorpt_correction_T_min  0.288
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.962
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             322
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-9 3 0 0.0969
0 -5 4 0.1390
1 0 0 0.1380
0 -1 -1 0.0845
0 -5 12 0.1351
0 8 -11 0.0743
1 12 -4 0.1133
0 6 12 0.1082

_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.21
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-9.0007 2.9993 0.0012 -0.0385 -0.1085 -1.0057
0.0000 -4.9985 4.0003 -0.4439 0.1868 0.1598
1.0001 -0.0000 -0.0001 0.0294 0.0189 0.1034
-0.0000 -0.9998 -1.0001 -0.0584 -0.0929 0.0166
0.0001 -4.9981 12.0011 -0.5790 0.7659 0.2281
-0.0001 7.9974 -11.0010 0.7879 -0.6319 -0.2950
1.0001 11.9969 -4.0004 1.0001 -0.0241 -0.2325
0.0001 5.9993 12.0012 0.2489 0.9918 -0.0485

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10884
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.955
_diffrn_reflns_theta_min         3.188
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00 102.00   1.00    1.09    --   12.43-178.00 -90.00   70
  2  ω    -69.00  47.00   1.00    1.09    --   12.43 -77.00   0.00  116
  3  ω    -22.00  94.00   1.00    1.09    --   12.43  77.00  90.00  116
  4  ω   -103.00 -32.00   1.00    1.09    --  -13.52 178.00 150.00   71
  5  ω    -16.00  90.00   1.00    1.09    --   12.43  37.00 -30.00  106
  6  ω    -77.00 -32.00   1.00    1.09    --   12.43 178.00-180.00   45
  7  ω    -64.00  44.00   1.00    1.09    --   12.43 -57.00-180.00  108
  8  ω     35.00 104.00   1.00    1.09    --   12.43 178.00-180.00   69
  9  ω    -64.00  13.00   1.00    1.09    --   12.43 -57.00  30.00   77
 10  ω    -25.00  29.00   1.00    1.09    --  -13.52 -99.00 150.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0293640000
_diffrn_orient_matrix_UB_12      0.0752830000
_diffrn_orient_matrix_UB_13      -0.0168959000
_diffrn_orient_matrix_UB_21      0.0189118000
_diffrn_orient_matrix_UB_22      0.0205445000
_diffrn_orient_matrix_UB_23      0.0723713000
_diffrn_orient_matrix_UB_31      0.1033541000
_diffrn_orient_matrix_UB_32      -0.0251528000
_diffrn_orient_matrix_UB_33      0.0085288000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2038
_reflns_number_total             2127
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Flack x determined using 900 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.048(5)
_refine_ls_extinction_coef       0.040(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2127
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0218
_refine_ls_restrained_S_all      1.095
_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)+(0.0203P)²+0.3597P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0493
_refine_ls_wR_factor_ref         0.0502
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups, All N(H,H,H) groups
2. Shared sites
{Y1, Yb1, Er1}
3. Uiso/Uaniso restraints and constraints
Uanis(Y1) = Uanis(Yb1) = Uanis(Er1)
4. Others
 Fixed Sof: Y1(0.91) Yb1(0.07) Er1(0.02)
5.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
5.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_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
Y1 Y 0.10573(5) 0.22489(4) 0.27123(3) 0.01178(15) Uani 0.91 1 d . . P . .
Yb1 Yb 0.10573(5) 0.22489(4) 0.27123(3) 0.01178(15) Uani 0.07 1 d . . P . .
Er1 Er 0.10573(5) 0.22489(4) 0.27123(3) 0.01178(15) Uani 0.02 1 d . . P . .
O1 O 0.0727(5) 0.4515(4) 0.1272(4) 0.0176(8) Uani 1 1 d . . . . .
O2 O 0.0008(6) 0.6118(4) -0.0538(4) 0.0223(8) Uani 1 1 d . . . . .
O3 O 0.1420(6) 0.4184(4) 0.4338(4) 0.0284(9) Uani 1 1 d . . . . .
O4 O 0.0604(6) 0.5795(5) 0.5890(4) 0.0313(10) Uani 1 1 d . . . . .
O5 O 0.4242(5) 0.2956(5) 0.2293(4) 0.0261(9) Uani 1 1 d . . . . .
O6 O 0.7552(5) 0.3017(5) 0.2215(4) 0.0294(9) Uani 1 1 d . . . . .
O7 O 0.3764(5) 0.1224(4) 0.4795(4) 0.0238(8) Uani 1 1 d . . . . .
O8 O 0.2826(6) -0.0270(4) 0.2945(4) 0.0238(8) Uani 1 1 d . . . . .
C1 C -0.0242(10) 0.4923(7) 0.0098(7) 0.0180(14) Uani 1 1 d . . . . .
H1 H -0.1271 0.4258 -0.0357 0.022 Uiso 1 1 calc R . . . .
C2 C 0.0446(11) 0.5106(10) 0.4807(9) 0.057(3) Uani 1 1 d . . . . .
H2 H -0.0758 0.5363 0.4167 0.069 Uiso 1 1 calc R . . . .
C3 C 0.5975(7) 0.2470(8) 0.2413(6) 0.0298(16) Uani 1 1 d . . . . .
H3 H 0.6122 0.1453 0.2728 0.036 Uiso 1 1 calc R . . . .
C4 C 0.3847(8) -0.0017(6) 0.4175(6) 0.0231(12) Uani 1 1 d . . . . .
H4 H 0.4697 -0.0795 0.4636 0.028 Uiso 1 1 calc R . . . .
C5 C 0.5281(11) 0.6664(7) 0.1347(7) 0.0385(16) Uani 1 1 d . . . . .
H5A H 0.5943 0.5667 0.1336 0.046 Uiso 1 1 calc R . . . .
H5B H 0.4439 0.6845 0.0414 0.046 Uiso 1 1 calc R . . . .
C6 C 0.6855(14) 0.7859(9) 0.1660(10) 0.066(3) Uani 1 1 d . . . . .
H6A H 0.7733 0.7795 0.0996 0.079 Uiso 1 1 calc GR . . . .
H6B H 0.7659 0.7712 0.2598 0.079 Uiso 1 1 calc GR . . . .
H6C H 0.6211 0.8857 0.1593 0.079 Uiso 1 1 calc GR . . . .
N1 N 0.3941(6) 0.6619(5) 0.2380(4) 0.0242(10) Uani 1 1 d . . . . .
H1A H 0.2959 0.5915 0.2113 0.029 Uiso 1 1 calc GR . . . .
H1B H 0.3369 0.7543 0.2421 0.029 Uiso 1 1 calc GR . . . .
H1C H 0.4687 0.6371 0.3226 0.029 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
Y1 O1 2.390(3) . ?
Y1 O2 2.296(3) 2_545 ?
Y1 O3 2.278(3) . ?
Y1 O4 2.301(4) 2_546 ?
Y1 O5 2.325(3) . ?
Y1 O6 2.374(4) 1_455 ?
Y1 O7 2.560(4) . ?
Y1 O8 2.464(3) . ?
O1 C1 1.235(8) . ?
O2 Y1 2.296(3) 2 ?
O2 Yb1 2.296(3) 2 ?
O2 Er1 2.296(3) 2 ?
O2 C1 1.233(8) . ?
O3 C2 1.179(8) . ?
O4 Y1 2.301(4) 2_556 ?
O4 Yb1 2.301(4) 2_556 ?
O4 Er1 2.301(4) 2_556 ?
O4 C2 1.193(8) . ?
O5 C3 1.210(6) . ?
O6 Y1 2.374(4) 1_655 ?
O6 Yb1 2.374(4) 1_655 ?
O6 Er1 2.374(4) 1_655 ?
O6 C3 1.204(6) . ?
O7 C4 1.238(6) . ?
O8 C4 1.260(6) . ?
C5 C6 1.456(9) . ?
C5 N1 1.479(7) . ?

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 Y1 O7 134.96(12) . . ?
O1 Y1 O8 139.55(13) . . ?
O2 Y1 O1 80.82(12) 2_545 . ?
O2 Y1 O4 102.51(15) 2_545 2_546 ?
O2 Y1 O5 93.68(14) 2_545 . ?
O2 Y1 O6 80.60(14) 2_545 1_455 ?
O2 Y1 O7 127.17(12) 2_545 . ?
O2 Y1 O8 75.78(12) 2_545 . ?
O3 Y1 O1 77.58(14) . . ?
O3 Y1 O2 156.34(13) . 2_545 ?
O3 Y1 O4 89.21(15) . 2_546 ?
O3 Y1 O5 87.88(14) . . ?
O3 Y1 O6 83.58(14) . 1_455 ?
O3 Y1 O7 75.87(13) . . ?
O3 Y1 O8 127.54(13) . . ?
O4 Y1 O1 142.94(13) 2_546 . ?
O4 Y1 O5 145.01(13) 2_546 . ?
O4 Y1 O6 72.35(14) 2_546 1_455 ?
O4 Y1 O7 71.98(13) 2_546 . ?
O4 Y1 O8 75.12(14) 2_546 . ?
O5 Y1 O1 69.79(12) . . ?
O5 Y1 O6 141.66(13) . 1_455 ?
O5 Y1 O7 73.50(13) . . ?
O5 Y1 O8 79.22(13) . . ?
O6 Y1 O1 71.87(12) 1_455 . ?
O6 Y1 O7 138.73(13) 1_455 . ?
O6 Y1 O8 134.07(13) 1_455 . ?
O8 Y1 O7 51.69(12) . . ?
C1 O1 Y1 137.6(4) . . ?
Y1 O2 Yb1 0.0 2 2 ?
Y1 O2 Er1 0.0 2 2 ?
Er1 O2 Yb1 0.00(2) 2 2 ?
C1 O2 Y1 140.3(4) . 2 ?
C1 O2 Yb1 140.3(4) . 2 ?
C1 O2 Er1 140.3(4) . 2 ?
C2 O3 Y1 141.2(4) . . ?
Yb1 O4 Y1 0.0 2_556 2_556 ?
Er1 O4 Y1 0.0 2_556 2_556 ?
Er1 O4 Yb1 0.000(13) 2_556 2_556 ?
C2 O4 Y1 146.1(4) . 2_556 ?
C2 O4 Yb1 146.1(4) . 2_556 ?
C2 O4 Er1 146.1(4) . 2_556 ?
C3 O5 Y1 141.1(4) . . ?
Yb1 O6 Y1 0.0 1_655 1_655 ?
Er1 O6 Y1 0.0 1_655 1_655 ?
Er1 O6 Yb1 0.00(2) 1_655 1_655 ?
C3 O6 Y1 135.3(4) . 1_655 ?
C3 O6 Yb1 135.3(4) . 1_655 ?
C3 O6 Er1 135.3(4) . 1_655 ?
C4 O7 Y1 90.8(3) . . ?
C4 O8 Y1 94.8(3) . . ?
O2 C1 O1 127.0(6) . . ?
O3 C2 O4 136.6(8) . . ?
O6 C3 O5 134.0(7) . . ?
O7 C4 O8 122.7(5) . . ?
C6 C5 N1 112.9(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.89 1.95 2.838(5) 172.0 .
N1 H1B O8 0.89 2.01 2.877(6) 163.3 1_565
N1 H1C O7 0.89 1.98 2.859(6) 169.2 2_656

_olex2_date_sample_data_collection 2017-01-17
_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 1.089
_oxdiff_exptl_absorpt_empirical_full_min 0.901
####################################################################### 
# 
# 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_EtAYbEr_293K
_database_code_depnum_ccdc_archive 'CCDC 1556097'
_audit_update_record             
;
2017-06-14 deposited with the CCDC.
2017-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H4 Er0.20 O8 Yb0.80, C2 H8 N'
_chemical_formula_sum            'C6 H12 Er0.20 N O8 Yb0.80'
_chemical_formula_weight         398.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Yb Yb -0.3850 5.5486 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.610(3)
_cell_length_b                   8.599(3)
_cell_length_c                   9.656(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.01(3)
_cell_angle_gamma                90
_cell_volume                     536.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7609
_cell_measurement_theta_min      3.1510
_cell_measurement_theta_max      29.2760

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.473
_exptl_crystal_F_000             377.2
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.195
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.084
_exptl_absorpt_coefficient_mu    8.637
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.336
_exptl_absorpt_correction_T_max  0.580
_exptl_absorpt_process_details   
;
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            10708
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.204
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2098
_reflns_number_gt                1973
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0083P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0129(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 872 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.073(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2098
_refine_ls_number_parameters     148
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0184
_refine_ls_wR_factor_ref         0.0331
_refine_ls_wR_factor_gt          0.0322
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Yb1 Yb 0.10477(3) 0.22514(6) 0.27064(2) 0.01325(12) Uani 0.8 1 d . . P . .
Er1 Er 0.10477(3) 0.22514(6) 0.27064(2) 0.01325(12) Uani 0.2 1 d . . P . .
O1 O 0.0722(7) 0.4486(6) 0.1264(5) 0.0225(11) Uani 1 1 d . . . . .
O2 O 0.0015(7) 0.6115(6) -0.0558(5) 0.0271(12) Uani 1 1 d . . . . .
O3 O 0.1406(7) 0.4200(6) 0.4297(5) 0.0305(13) Uani 1 1 d . . . . .
O4 O 0.0618(7) 0.5833(6) 0.5868(6) 0.0334(14) Uani 1 1 d . . . . .
O5 O 0.4215(6) 0.2945(6) 0.2287(6) 0.0288(13) Uani 1 1 d . . . . .
O6 O 0.7562(7) 0.3001(6) 0.2209(6) 0.0357(15) Uani 1 1 d . . . . .
O7 O 0.3764(7) 0.1254(6) 0.4803(5) 0.0292(12) Uani 1 1 d . . . . .
O8 O 0.2807(7) -0.0251(6) 0.2944(6) 0.0288(13) Uani 1 1 d . . . . .
C1 C -0.0242(19) 0.4905(15) 0.0086(16) 0.023(3) Uani 1 1 d . . . . .
H1 H -0.1278 0.4238 -0.0369 0.027 Uiso 1 1 calc R U . . .
C2 C 0.0420(14) 0.5036(16) 0.4876(16) 0.069(5) Uani 1 1 d . . . . .
H2 H -0.0945 0.5063 0.4378 0.083 Uiso 1 1 calc R U . . .
C3 C 0.5972(10) 0.246(2) 0.2405(8) 0.038(3) Uani 1 1 d . . . . .
H3 H 0.6115 0.1434 0.2719 0.046 Uiso 1 1 calc R U . . .
C4 C 0.3841(11) -0.0014(9) 0.4156(9) 0.0294(19) Uani 1 1 d . . . . .
H4 H 0.4704 -0.0799 0.4602 0.035 Uiso 1 1 calc R U . . .
C5 C 0.5316(14) 0.6643(10) 0.1349(9) 0.043(2) Uani 1 1 d . . . . .
H5A H 0.4507 0.6851 0.0408 0.052 Uiso 1 1 calc R U . . .
H5B H 0.5956 0.5630 0.1333 0.052 Uiso 1 1 calc R U . . .
C6 C 0.6956(17) 0.7847(11) 0.1722(13) 0.077(4) Uani 1 1 d . . . . .
H6A H 0.7985 0.7692 0.1165 0.092 Uiso 1 1 calc R U . . .
H6B H 0.7588 0.7764 0.2709 0.092 Uiso 1 1 calc R U . . .
H6C H 0.6354 0.8861 0.1534 0.092 Uiso 1 1 calc R U . . .
N1 N 0.3925(8) 0.6619(7) 0.2377(6) 0.0296(16) Uani 1 1 d . . . . .
H1A H 0.2917 0.5931 0.2096 0.036 Uiso 1 1 calc R U . . .
H1B H 0.3378 0.7559 0.2421 0.036 Uiso 1 1 calc R U . . .
H1C H 0.4645 0.6354 0.3228 0.036 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Yb1 O3 2.252(5) . ?
Yb1 O2 2.268(5) 2_545 ?
Yb1 O4 2.286(5) 2_546 ?
Yb1 O5 2.293(4) . ?
Yb1 O6 2.344(5) 1_455 ?
Yb1 O1 2.357(5) . ?
Yb1 O8 2.434(5) . ?
Yb1 O7 2.558(5) . ?
O1 C1 1.236(16) . ?
O2 C1 1.242(15) . ?
O2 Er1 2.268(5) 2 ?
O2 Yb1 2.268(5) 2 ?
O3 C2 1.186(13) . ?
O4 C2 1.163(13) . ?
O4 Yb1 2.286(5) 2_556 ?
O4 Er1 2.286(5) 2_556 ?
O5 C3 1.217(9) . ?
O6 C3 1.201(10) . ?
O6 Er1 2.344(5) 1_655 ?
O6 Yb1 2.344(5) 1_655 ?
O7 C4 1.263(9) . ?
O8 C4 1.243(9) . ?
C5 N1 1.487(10) . ?
C5 C6 1.488(11) . ?

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 Yb1 O2 155.91(19) . 2_545 ?
O3 Yb1 O4 89.0(2) . 2_546 ?
O2 Yb1 O4 103.0(2) 2_545 2_546 ?
O3 Yb1 O5 87.51(18) . . ?
O2 Yb1 O5 94.07(18) 2_545 . ?
O4 Yb1 O5 144.81(18) 2_546 . ?
O3 Yb1 O6 83.96(19) . 1_455 ?
O2 Yb1 O6 80.02(19) 2_545 1_455 ?
O4 Yb1 O6 72.19(18) 2_546 1_455 ?
O5 Yb1 O6 141.91(18) . 1_455 ?
O3 Yb1 O1 77.3(2) . . ?
O2 Yb1 O1 80.7(2) 2_545 . ?
O4 Yb1 O1 142.64(17) 2_546 . ?
O5 Yb1 O1 69.99(16) . . ?
O6 Yb1 O1 71.92(17) 1_455 . ?
O3 Yb1 O8 127.82(18) . . ?
O2 Yb1 O8 75.90(18) 2_545 . ?
O4 Yb1 O8 75.63(19) 2_546 . ?
O5 Yb1 O8 79.09(17) . . ?
O6 Yb1 O8 133.82(19) 1_455 . ?
O1 Yb1 O8 139.44(18) . . ?
O3 Yb1 O7 75.69(18) . . ?
O2 Yb1 O7 127.74(18) 2_545 . ?
O4 Yb1 O7 72.02(17) 2_546 . ?
O5 Yb1 O7 73.19(16) . . ?
O6 Yb1 O7 138.81(17) 1_455 . ?
O1 Yb1 O7 134.72(16) . . ?
O8 Yb1 O7 52.14(17) . . ?
C1 O1 Yb1 138.4(8) . . ?
C1 O2 Er1 140.4(8) . 2 ?
C1 O2 Yb1 140.4(8) . 2 ?
Er1 O2 Yb1 0.0 2 2 ?
C2 O3 Yb1 141.5(6) . . ?
C2 O4 Yb1 145.6(6) . 2_556 ?
C2 O4 Er1 145.6(6) . 2_556 ?
Yb1 O4 Er1 0.0 2_556 2_556 ?
C3 O5 Yb1 141.5(9) . . ?
C3 O6 Er1 135.8(8) . 1_655 ?
C3 O6 Yb1 135.8(8) . 1_655 ?
Er1 O6 Yb1 0.0 1_655 1_655 ?
C4 O7 Yb1 89.5(4) . . ?
C4 O8 Yb1 95.9(5) . . ?
O1 C1 O2 127.4(13) . . ?
O4 C2 O3 140.1(10) . . ?
O6 C3 O5 134.5(16) . . ?
O8 C4 O7 122.4(7) . . ?
N1 C5 C6 111.6(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.89 1.95 2.838(8) 173.6 .
N1 H1C O7 0.89 1.97 2.849(8) 167.5 2_656
N1 H1B O8 0.89 2.01 2.873(8) 164.7 1_565

_refine_diff_density_max         1.007
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_EtAYEu_293K
_database_code_depnum_ccdc_archive 'CCDC 1556098'
_audit_update_record             
;
2017-06-14 deposited with the CCDC.
2017-08-14 downloaded from the CCDC.
;
_audit_creation_date             2017-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H4 Eu0.08 O8 Y0.92, C2 H8 N'
_chemical_formula_sum            'C6 H12 Eu0.08 N O8 Y0.92'
_chemical_formula_weight         320.12
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 H12 N1 O8 Y0.95 Eu0.05'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Y Y -2.7962 3.5667 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.663(3)
_cell_length_b                   8.658(3)
_cell_length_c                   9.716(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.45(3)
_cell_angle_gamma                90
_cell_volume                     547.3(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6945
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9120
_cell_measurement_theta_min      3.1350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.388
_exptl_absorpt_correction_T_max  0.576
_exptl_absorpt_correction_T_min  0.331
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.942
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             320
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 4 -5 0.0553
0 -5 -1 0.1122
0 0 -1 0.1027
5 2 0 0.0956
0 -1 1 0.0601
-5 -1 1 0.1486
0 1 1 0.0383
0 5 1 0.0454
0 -4 -5 0.1113
0 1 5 0.0520

_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.117
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0009 3.9973 -4.9981 -0.1370 0.4470 -0.1681
-0.0002 -4.9977 -0.9983 0.3989 -0.1185 -0.0086
0.0001 -0.0002 -0.9994 0.0314 0.0607 -0.0302
4.9979 1.9992 -0.0010 -0.1249 0.1809 0.5248
-0.0002 -0.9994 0.9997 0.0421 -0.0966 0.0345
-4.9979 -0.9996 1.0002 0.0201 -0.2057 -0.4989
-0.0001 0.9997 0.9992 -0.1049 -0.0249 0.0259
0.0002 4.9977 0.9983 -0.3989 0.1185 0.0086
0.0003 -3.9988 -4.9963 0.4509 0.1603 -0.1336
-0.0005 1.0003 4.9970 -0.2304 -0.2678 0.1466

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10805
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         3.185
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  94.00   1.00    2.35    --   12.43  77.00 -30.00  116
  2  ω    -22.00  94.00   1.00    2.35    --   12.43  77.00-180.00  116
  3  ω    -48.00  68.00   1.00    2.35    --  -13.52  77.00  60.00  116
  4  ω    -25.00  55.00   1.00    2.35    --   12.43 -99.00-150.00   80
  5  ω     35.00 104.00   1.00    2.35    --   12.43 178.00  90.00   69
  6  ω      9.00  80.00   1.00    2.35    --   12.43-142.00 -54.00   71
  7  ω    -93.00 -16.00   1.00    2.35    --  -13.52 156.00-162.54   77
  8  ω   -105.00 -35.00   1.00    2.35    --  -13.52-178.00  60.00   70
  9  ω    -91.00  15.00   1.00    2.35    --  -13.52 -37.00  30.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0044127000
_diffrn_orient_matrix_UB_12      -0.0735371000
_diffrn_orient_matrix_UB_13      -0.0313937000
_diffrn_orient_matrix_UB_21      0.0218386000
_diffrn_orient_matrix_UB_22      0.0358379000
_diffrn_orient_matrix_UB_23      -0.0607588000
_diffrn_orient_matrix_UB_31      0.1067296000
_diffrn_orient_matrix_UB_32      -0.0043117000
_diffrn_orient_matrix_UB_33      0.0302022000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2024
_reflns_number_total             2136
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 897 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.062(4)
_refine_ls_extinction_coef       0.036(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2136
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0201
_refine_ls_restrained_S_all      1.073
_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)+(0.0180P)²+0.3140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0447
_refine_ls_wR_factor_ref         0.0455
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups, All N(H,H,H) groups
2. Shared sites
{Y1, Eu1}
3. Uiso/Uaniso restraints and constraints
Uanis(Y1) = Uanis(Eu1)
4. Others
 Fixed Sof: Y1(0.92) Eu1(0.08)
5.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
5.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_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
Y1 Y -0.10588(4) -0.22514(4) -0.27126(3) 0.01226(13) Uani 0.92 1 d . . P . .
Eu1 Eu -0.10588(4) -0.22514(4) -0.27126(3) 0.01226(13) Uani 0.08 1 d . . P . .
O1 O -0.0729(5) -0.4520(4) -0.1271(3) 0.0198(7) Uani 1 1 d . . . . .
O2 O -0.0008(5) -0.6122(4) 0.0537(3) 0.0238(8) Uani 1 1 d . . . . .
O3 O -0.1417(5) -0.4180(4) -0.4340(3) 0.0296(9) Uani 1 1 d . . . . .
O4 O -0.0606(5) -0.5796(5) -0.5892(4) 0.0316(9) Uani 1 1 d . . . . .
O5 O -0.4245(4) -0.2956(4) -0.2292(3) 0.0271(8) Uani 1 1 d . . . . .
O6 O -0.7554(5) -0.3016(4) -0.2218(4) 0.0291(8) Uani 1 1 d . . . . .
O7 O -0.3759(5) -0.1225(4) -0.4798(3) 0.0244(7) Uani 1 1 d . . . . .
O8 O -0.2824(5) 0.0272(4) -0.2947(3) 0.0251(8) Uani 1 1 d . . . . .
C1 C 0.0249(9) -0.4927(7) -0.0090(7) 0.0192(13) Uani 1 1 d . . . . .
H1 H 0.1276 -0.4263 0.0366 0.023 Uiso 1 1 calc R . . . .
C2 C -0.0453(9) -0.5108(9) -0.4805(7) 0.059(3) Uani 1 1 d . . . . .
H2 H 0.0739 -0.5378 -0.4159 0.070 Uiso 1 1 calc R . . . .
C3 C -0.5981(7) -0.2465(9) -0.2408(5) 0.0325(15) Uani 1 1 d . . . . .
H3 H -0.6124 -0.1444 -0.2710 0.039 Uiso 1 1 calc R . . . .
C4 C -0.3843(7) 0.0011(6) -0.4177(5) 0.0248(11) Uani 1 1 d . . . . .
H4 H -0.4699 0.0785 -0.4638 0.030 Uiso 1 1 calc R . . . .
C5 C -0.5291(10) -0.6656(6) -0.1350(6) 0.0404(14) Uani 1 1 d . . . . .
H5A H -0.4453 -0.6828 -0.0414 0.048 Uiso 1 1 calc R . . . .
H5B H -0.5960 -0.5662 -0.1348 0.048 Uiso 1 1 calc R . . . .
C6 C -0.6862(12) -0.7868(8) -0.1667(9) 0.069(2) Uani 1 1 d . . . . .
H6A H -0.7763 -0.7793 -0.1020 0.083 Uiso 1 1 calc GR . . . .
H6B H -0.6209 -0.8862 -0.1573 0.083 Uiso 1 1 calc GR . . . .
H6C H -0.7641 -0.7741 -0.2613 0.083 Uiso 1 1 calc GR . . . .
N1 N -0.3949(6) -0.6621(5) -0.2380(4) 0.0262(10) Uani 1 1 d . . . . .
H1A H -0.2966 -0.5919 -0.2116 0.031 Uiso 1 1 calc GR . . . .
H1B H -0.4693 -0.6376 -0.3227 0.031 Uiso 1 1 calc GR . . . .
H1C H -0.3381 -0.7546 -0.2418 0.031 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
Y1 O1 2.395(3) . ?
Y1 O2 2.298(3) 2 ?
Y1 O3 2.276(3) . ?
Y1 O4 2.303(3) 2_554 ?
Y1 O5 2.328(3) . ?
Y1 O6 2.375(3) 1_655 ?
Y1 O7 2.561(3) . ?
Y1 O8 2.468(3) . ?
O1 C1 1.242(7) . ?
O2 Y1 2.298(3) 2_545 ?
O2 Eu1 2.298(3) 2_545 ?
O2 C1 1.231(7) . ?
O3 C2 1.178(7) . ?
O4 Y1 2.303(3) 2_544 ?
O4 Eu1 2.303(3) 2_544 ?
O4 C2 1.198(7) . ?
O5 C3 1.215(6) . ?
O6 Y1 2.375(3) 1_455 ?
O6 Eu1 2.375(3) 1_455 ?
O6 C3 1.201(6) . ?
O7 C4 1.236(6) . ?
O8 C4 1.261(6) . ?
C5 C6 1.467(8) . ?
C5 N1 1.480(7) . ?

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 Y1 O7 135.03(11) . . ?
O1 Y1 O8 139.63(11) . . ?
O2 Y1 O1 80.80(11) 2 . ?
O2 Y1 O4 102.46(13) 2 2_554 ?
O2 Y1 O5 93.62(12) 2 . ?
O2 Y1 O6 80.60(13) 2 1_655 ?
O2 Y1 O7 127.25(11) 2 . ?
O2 Y1 O8 75.82(11) 2 . ?
O3 Y1 O1 77.71(13) . . ?
O3 Y1 O2 156.38(12) . 2 ?
O3 Y1 O4 89.10(14) . 2_554 ?
O3 Y1 O5 88.08(13) . . ?
O3 Y1 O6 83.55(13) . 1_655 ?
O3 Y1 O7 75.78(12) . . ?
O3 Y1 O8 127.49(11) . . ?
O4 Y1 O1 142.92(12) 2_554 . ?
O4 Y1 O5 145.05(11) 2_554 . ?
O4 Y1 O6 72.20(12) 2_554 1_655 ?
O4 Y1 O7 71.92(11) 2_554 . ?
O4 Y1 O8 75.03(13) 2_554 . ?
O5 Y1 O1 69.80(11) . . ?
O5 Y1 O6 141.78(12) . 1_655 ?
O5 Y1 O7 73.63(11) . . ?
O5 Y1 O8 79.27(12) . . ?
O6 Y1 O1 71.98(11) 1_655 . ?
O6 Y1 O7 138.52(11) 1_655 . ?
O6 Y1 O8 133.91(12) 1_655 . ?
O8 Y1 O7 51.72(10) . . ?
C1 O1 Y1 137.4(4) . . ?
Y1 O2 Eu1 0.000(1) 2_545 2_545 ?
C1 O2 Y1 139.9(4) . 2_545 ?
C1 O2 Eu1 139.9(4) . 2_545 ?
C2 O3 Y1 141.5(4) . . ?
Eu1 O4 Y1 0.0 2_544 2_544 ?
C2 O4 Y1 146.2(4) . 2_544 ?
C2 O4 Eu1 146.2(4) . 2_544 ?
C3 O5 Y1 141.1(4) . . ?
Eu1 O6 Y1 0.0 1_455 1_455 ?
C3 O6 Y1 135.3(4) . 1_455 ?
C3 O6 Eu1 135.3(4) . 1_455 ?
C4 O7 Y1 90.7(3) . . ?
C4 O8 Y1 94.5(3) . . ?
O2 C1 O1 126.5(6) . . ?
O3 C2 O4 136.7(7) . . ?
O6 C3 O5 133.8(7) . . ?
O7 C4 O8 123.1(4) . . ?
C6 C5 N1 112.4(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.89 1.96 2.842(5) 171.8 .
N1 H1B O7 0.89 1.98 2.857(5) 169.5 2_444
N1 H1C O8 0.89 2.01 2.878(5) 163.4 1_545

_olex2_date_sample_data_collection 2017-01-17
_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 1.125
_oxdiff_exptl_absorpt_empirical_full_min 0.918
