# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_amoac_1nov
_database_code_depnum_ccdc_archive 'CCDC 2016262'
loop_
_audit_author_name
_audit_author_address
'Frankie White'
;Los Alamos National Laboratory
United States of America
;
_audit_update_record             
;
2020-07-14 deposited with the CCDC.	2021-03-17 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT973_amoac_1nov          
;
PROBLEM: Check Calcd Positive Resid. Density on       Am1       2.23 eA-3
RESPONSE: Structure was checked for twinning. No twinning observed. 
;
# Added during the CSD deposition process: Tuesday 14 July 2020 04:01 PM
# end Validation Reply Form

_audit_creation_date             2019-11-26
_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         
'Am H2O 3(C2 O2 H3) 2(C2 O2 H3) 2(N) + [solvent]'
_chemical_formula_sum            'Am O11 N2 C10 H17'
_chemical_formula_weight         582.52
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Pu Pu -9.4100 4.3056 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Am Am -7.8986 4.5125 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.7963(3)
_cell_length_b                   15.0543(8)
_cell_length_c                   20.4812(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.2970(10)
_cell_angle_gamma                90
_cell_volume                     2078.53(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      33.57
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   0.371
_shelx_estimated_absorpt_T_min   0.137
_exptl_absorpt_coefficient_mu    3.739
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.5233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1195 before and 0.0485 after correction. The Ratio of minimum to maximum transmission is 0.7008. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            peach
_exptl_crystal_density_diffrn    1.884
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rectangular blocks'
_exptl_crystal_F_000             1219
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            47585
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.733
_diffrn_reflns_theta_min         2.706
_diffrn_ambient_temperature      298.39
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7049
_reflns_number_total             8271
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.366
_refine_diff_density_min         -0.868
_refine_diff_density_rms         0.206
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         8271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0284
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0382P)²+2.2947P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0749
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O11(H11A,H11B)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C9(H9A,H9B,H9C), C1(H1A,H1B,H1C), C5(H5A,H5B,H5C), C7(H7A,
 H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Am1 Am 0.53107(2) 0.59582(2) 0.78159(2) 0.02263(4) Uani 1 1 d . . . . .
O4 O 0.4045(3) 0.46776(16) 0.84780(13) 0.0363(5) Uani 1 1 d . . . . .
O9 O -0.1291(3) 0.64330(19) 0.79693(13) 0.0392(6) Uani 1 1 d . . . . .
O2 O 0.4973(4) 0.75235(17) 0.82807(13) 0.0428(6) Uani 1 1 d . . . . .
O3 O 0.7258(3) 0.47534(18) 0.85025(14) 0.0410(6) Uani 1 1 d . . . . .
O10 O 0.1791(3) 0.6180(2) 0.78414(15) 0.0439(6) Uani 1 1 d . . . . .
O7 O 0.4200(5) 0.7936(2) 0.61659(14) 0.0520(7) Uani 1 1 d . . . . .
O8 O 0.4963(4) 0.6856(2) 0.68648(13) 0.0447(6) Uani 1 1 d . . . . .
O1 O 0.5385(5) 0.64705(17) 0.90140(12) 0.0448(6) Uani 1 1 d . . . . .
O5 O 0.6940(4) 0.4939(2) 0.70465(15) 0.0497(7) Uani 1 1 d . . . . .
O6 O 0.3722(5) 0.4815(2) 0.70036(15) 0.0531(7) Uani 1 1 d . . . . .
N2 N 0.3602(5) 0.8838(2) 0.50204(14) 0.0387(7) Uani 1 1 d . . . . .
O11 O 0.4579(5) 0.89420(19) 0.7351(2) 0.0496(7) Uani 1 1 d . . . . .
H11A H 0.458873 0.862851 0.700620 0.074 Uiso 1 1 d G . . . .
H11B H 0.467894 0.856729 0.766429 0.074 Uiso 1 1 d G . . . .
C4 C 0.5757(5) 0.4427(2) 0.87110(16) 0.0288(6) Uani 1 1 d . . . . .
N1 N 1.0908(5) 0.5413(3) 0.91197(16) 0.0479(8) Uani 1 1 d . . . . .
C10 C 0.0217(4) 0.6594(2) 0.76998(15) 0.0272(5) Uani 1 1 d . . . . .
C2 C 0.5097(5) 0.7281(2) 0.88610(17) 0.0348(7) Uani 1 1 d . . . . .
C8 C 0.4691(5) 0.7155(2) 0.62930(16) 0.0349(7) Uani 1 1 d . . . . .
C6 C 0.5320(7) 0.4591(3) 0.6807(2) 0.0448(9) Uani 1 1 d . . . . .
C3 C 0.5996(6) 0.3740(3) 0.9245(2) 0.0467(9) Uani 1 1 d . . . . .
H3A H 0.728491 0.347279 0.926417 0.070 Uiso 1 1 calc GR . . . .
H3B H 0.499543 0.329140 0.915260 0.070 Uiso 1 1 calc GR . . . .
H3C H 0.586174 0.401559 0.965946 0.070 Uiso 1 1 calc GR . . . .
C9 C 0.0108(6) 0.7327(3) 0.7208(2) 0.0558(12) Uani 1 1 d . . . . .
H9A H -0.116126 0.731427 0.694228 0.084 Uiso 1 1 calc GR . . . .
H9B H 0.113724 0.725139 0.693244 0.084 Uiso 1 1 calc GR . . . .
H9C H 0.027747 0.788621 0.743291 0.084 Uiso 1 1 calc GR . . . .
C1 C 0.4891(9) 0.7932(3) 0.9402(3) 0.0691(15) Uani 1 1 d . . . . .
H1A H 0.465029 0.851370 0.921770 0.104 Uiso 1 1 calc GR . . . .
H1B H 0.609096 0.793818 0.970511 0.104 Uiso 1 1 calc GR . . . .
H1C H 0.380076 0.775976 0.962976 0.104 Uiso 1 1 calc GR . . . .
C5 C 0.5311(11) 0.3914(4) 0.6268(4) 0.088(2) Uani 1 1 d . . . . .
H5A H 0.431043 0.347562 0.631287 0.132 Uiso 1 1 calc GR . . . .
H5B H 0.658544 0.363107 0.629873 0.132 Uiso 1 1 calc GR . . . .
H5C H 0.503067 0.420144 0.584820 0.132 Uiso 1 1 calc GR . . . .
C7 C 0.5017(12) 0.6551(4) 0.5736(3) 0.090(2) Uani 1 1 d . . . . .
H7A H 0.410672 0.606186 0.572106 0.135 Uiso 1 1 calc GR . . . .
H7B H 0.635309 0.633049 0.580155 0.135 Uiso 1 1 calc GR . . . .
H7C H 0.480158 0.687397 0.532934 0.135 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
Am1 O4 2.567(2) . ?
Am1 O9 2.400(2) 1_655 ?
Am1 O2 2.563(3) . ?
Am1 O3 2.558(2) . ?
Am1 O10 2.422(2) . ?
Am1 O8 2.358(2) . ?
Am1 O1 2.566(3) . ?
Am1 O5 2.551(3) . ?
Am1 O6 2.538(3) . ?
Am1 C4 2.937(3) . ?
Am1 C2 2.940(3) . ?
Am1 C6 2.917(4) . ?
O4 C4 1.258(4) . ?
O9 C10 1.248(3) . ?
O2 C2 1.236(4) . ?
O3 C4 1.255(4) . ?
O10 C10 1.241(4) . ?
O7 C8 1.241(4) . ?
O8 C8 1.246(4) . ?
O1 C2 1.268(4) . ?
O5 C6 1.261(5) . ?
O6 C6 1.251(5) . ?
C4 C3 1.499(5) . ?
C10 C9 1.489(5) . ?
C2 C1 1.499(5) . ?
C8 C7 1.496(6) . ?
C6 C5 1.502(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
O4 Am1 C4 25.29(8) . . ?
O4 Am1 C2 94.19(9) . . ?
O4 Am1 C6 82.86(11) . . ?
O9 Am1 O4 122.41(8) 1_655 . ?
O9 Am1 O2 78.90(10) 1_655 . ?
O9 Am1 O3 73.58(8) 1_655 . ?
O9 Am1 O10 153.21(11) 1_655 . ?
O9 Am1 O1 83.31(10) 1_655 . ?
O9 Am1 O5 76.93(10) 1_655 . ?
O9 Am1 O6 127.59(10) 1_655 . ?
O9 Am1 C4 97.52(9) 1_655 . ?
O9 Am1 C2 80.72(10) 1_655 . ?
O9 Am1 C6 102.36(11) 1_655 . ?
O2 Am1 O4 116.27(8) . . ?
O2 Am1 O1 50.24(8) . . ?
O2 Am1 C4 119.80(8) . . ?
O2 Am1 C2 24.76(9) . . ?
O2 Am1 C6 156.95(10) . . ?
O3 Am1 O4 50.35(7) . . ?
O3 Am1 O2 120.81(9) . . ?
O3 Am1 O1 75.02(9) . . ?
O3 Am1 C4 25.22(8) . . ?
O3 Am1 C2 98.62(10) . . ?
O3 Am1 C6 80.90(11) . . ?
O10 Am1 O4 72.19(8) . . ?
O10 Am1 O2 74.34(10) . . ?
O10 Am1 O3 121.94(8) . . ?
O10 Am1 O1 80.66(10) . . ?
O10 Am1 O5 127.13(10) . . ?
O10 Am1 O6 76.62(11) . . ?
O10 Am1 C4 96.81(9) . . ?
O10 Am1 C2 75.57(11) . . ?
O10 Am1 C6 101.74(12) . . ?
O8 Am1 O4 149.50(9) . . ?
O8 Am1 O9 86.05(9) . 1_655 ?
O8 Am1 O2 77.02(9) . . ?
O8 Am1 O3 148.32(9) . . ?
O8 Am1 O10 86.75(10) . . ?
O8 Am1 O1 127.25(9) . . ?
O8 Am1 O5 80.81(10) . . ?
O8 Am1 O6 81.82(11) . . ?
O8 Am1 C4 163.16(10) . . ?
O8 Am1 C2 101.78(10) . . ?
O8 Am1 C6 80.10(11) . . ?
O1 Am1 O4 71.81(9) . . ?
O1 Am1 C4 69.58(8) . . ?
O1 Am1 C2 25.49(9) . . ?
O1 Am1 C6 152.60(10) . . ?
O5 Am1 O4 94.33(10) . . ?
O5 Am1 O2 148.09(10) . . ?
O5 Am1 O3 71.23(10) . . ?
O5 Am1 O1 144.48(9) . . ?
O5 Am1 C4 83.97(10) . . ?
O5 Am1 C2 157.28(10) . . ?
O5 Am1 C6 25.56(11) . . ?
O6 Am1 O4 72.17(10) . . ?
O6 Am1 O2 144.75(10) . . ?
O6 Am1 O3 91.53(11) . . ?
O6 Am1 O1 141.79(10) . . ?
O6 Am1 O5 50.87(9) . . ?
O6 Am1 C4 83.01(10) . . ?
O6 Am1 C2 151.68(10) . . ?
O6 Am1 C6 25.32(11) . . ?
C4 Am1 C2 95.04(9) . . ?
C6 Am1 C4 83.07(11) . . ?
C6 Am1 C2 176.55(11) . . ?
C4 O4 Am1 94.01(19) . . ?
C10 O9 Am1 146.2(2) . 1_455 ?
C2 O2 Am1 95.0(2) . . ?
C4 O3 Am1 94.51(19) . . ?
C10 O10 Am1 152.8(2) . . ?
C8 O8 Am1 166.0(3) . . ?
C2 O1 Am1 94.0(2) . . ?
C6 O5 Am1 93.7(2) . . ?
C6 O6 Am1 94.5(2) . . ?
O4 C4 Am1 60.70(16) . . ?
O4 C4 C3 119.6(3) . . ?
O3 C4 Am1 60.27(16) . . ?
O3 C4 O4 120.4(3) . . ?
O3 C4 C3 120.0(3) . . ?
C3 C4 Am1 171.9(3) . . ?
O9 C10 C9 118.0(3) . . ?
O10 C10 O9 122.1(3) . . ?
O10 C10 C9 119.8(3) . . ?
O2 C2 Am1 60.26(19) . . ?
O2 C2 O1 120.8(3) . . ?
O2 C2 C1 121.1(4) . . ?
O1 C2 Am1 60.55(18) . . ?
O1 C2 C1 118.2(3) . . ?
C1 C2 Am1 177.0(3) . . ?
O7 C8 O8 122.9(4) . . ?
O7 C8 C7 118.5(3) . . ?
O8 C8 C7 118.6(4) . . ?
O5 C6 Am1 60.8(2) . . ?
O5 C6 C5 119.3(5) . . ?
O6 C6 Am1 60.2(2) . . ?
O6 C6 O5 120.9(4) . . ?
O6 C6 C5 119.7(5) . . ?
C5 C6 Am1 177.9(4) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.499 0.000 0.000 122.1 37.4 ?
2 -0.384 0.500 0.500 122.1 37.4 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cmoac_1
_database_code_depnum_ccdc_archive 'CCDC 2016265'
loop_
_audit_author_name
_audit_author_address
'Frankie White'
;Los Alamos National Laboratory
United States of America
;
_audit_update_record             
;
2020-07-14 deposited with the CCDC.	2021-03-17 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT307_cmoac_1             
;
PROBLEM: Isolated Metal Atom found in Structure (Unusual)        Cm1 Check
RESPONSE: Heavy Metal Curium
;
_vrf_PLAT417_cmoac_1             
;
PROBLEM: Short Inter D-H..H-D       H2B      ..H11B     .       1.47 Ang.
RESPONSE: Hydrogens for Ammoniun Site were placed in most likely orientation
;
# Added during the CSD deposition process: Tuesday 14 July 2020 04:01 PM
# end Validation Reply Form

_audit_creation_date             2019-11-06
_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         
'Cm H2O 3(C2 O2 H3) 2(C2 O2 H3) 2(N H4) + [solvent]'
_chemical_formula_sum            'Cm O11 N2 C10 H25'
_chemical_formula_weight         593.51
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cm Cm -7.3248 4.8980 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.7801(3)
_cell_length_b                   15.0056(7)
_cell_length_c                   20.4890(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.2400(10)
_cell_angle_gamma                90
_cell_volume                     2067.92(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9735
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.989
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1074 before and 0.0468 after correction.
The Ratio of minimum to maximum transmission is 0.6662.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            lemonade
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.880
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rectangular blocks'
_exptl_crystal_F_000             1100
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            32150
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.271
_diffrn_reflns_theta_min         2.715
_diffrn_ambient_temperature      298.06
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4603
_reflns_number_total             5093
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.823
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.183
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         5093
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0252
_refine_ls_restrained_S_all      1.171
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0340P)²+2.2266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0652
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Riding coordinates:
 N1(H1D,H1E,H1F), N1(H1G), N2(H2A,H2B,H2C), N2(H2D)
2.b Free rotating group:
 O11(H11A,H11B)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C1(H1A,H1B,H1C), C7(H7A,H7B,H7C), C5(H5A,H5B,H5C), C9(H9A,
 H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cm1 Cm 0.53075(2) 0.59590(2) 0.28222(2) 0.02372(5) Uani 1 1 d . . . . .
O4 O 0.4049(4) 0.46790(19) 0.34824(15) 0.0379(7) Uani 1 1 d . . . . .
O10 O 0.4176(6) 0.7919(2) 0.11635(16) 0.0527(9) Uani 1 1 d . . . . .
O1 O 0.4996(5) 0.7526(2) 0.32807(15) 0.0426(7) Uani 1 1 d . . . . .
O6 O -0.1298(4) 0.6432(2) 0.29699(15) 0.0397(7) Uani 1 1 d . . . . .
O3 O 0.7259(4) 0.4759(2) 0.35073(16) 0.0421(7) Uani 1 1 d . . . . .
N1 N 0.4584(5) 0.8934(2) 0.2351(2) 0.0376(8) Uani 1 1 d . . . . .
H1D H 0.452290 0.951229 0.225350 0.045 Uiso 1 1 d R . . . .
H1E H 0.360690 0.879459 0.258480 0.045 Uiso 1 1 d R . . . .
H1F H 0.575030 0.881289 0.258480 0.045 Uiso 1 1 d R . . . .
H1G H 0.445350 0.860989 0.197270 0.045 Uiso 1 1 d R . . . .
O5 O 0.1810(4) 0.6192(2) 0.28563(18) 0.0457(8) Uani 1 1 d . . . . .
O8 O 0.6915(5) 0.4940(2) 0.20560(17) 0.0506(8) Uani 1 1 d . . . . .
O2 O 0.5387(5) 0.6474(2) 0.40152(15) 0.0451(7) Uani 1 1 d . . . . .
O9 O 0.4961(5) 0.6856(2) 0.18760(15) 0.0452(8) Uani 1 1 d . . . . .
O7 O 0.3688(5) 0.4826(2) 0.20167(18) 0.0538(9) Uani 1 1 d . . . . .
N2 N -0.1405(5) 0.6167(2) 0.50234(16) 0.0368(8) Uani 1 1 d . . . . .
H2A H -0.246280 0.643811 0.480969 0.044 Uiso 1 1 d R . . . .
H2B H -0.180140 0.573571 0.527479 0.044 Uiso 1 1 d R . . . .
H2C H -0.068040 0.656131 0.527479 0.044 Uiso 1 1 d R . . . .
H2D H -0.065820 0.592921 0.472779 0.044 Uiso 1 1 d R . . . .
C4 C 0.5753(6) 0.4433(3) 0.37142(19) 0.0288(7) Uani 1 1 d . . . . .
O11 O 0.0884(5) 0.5422(3) 0.4118(2) 0.0679(11) Uani 1 1 d . . . . .
H11A H 0.187962 0.561021 0.394413 0.102 Uiso 1 1 d G . . . .
H11B H 0.138758 0.517320 0.447314 0.102 Uiso 1 1 d G . . . .
C6 C 0.0211(5) 0.6588(3) 0.27036(19) 0.0303(8) Uani 1 1 d . . . . .
C10 C 0.4679(6) 0.7140(3) 0.1298(2) 0.0369(9) Uani 1 1 d . . . . .
C2 C 0.5128(6) 0.7288(3) 0.3863(2) 0.0365(9) Uani 1 1 d . . . . .
C8 C 0.5291(7) 0.4589(3) 0.1820(2) 0.0454(11) Uani 1 1 d . . . . .
C3 C 0.5999(8) 0.3739(4) 0.4244(2) 0.0486(11) Uani 1 1 d . . . . .
H3A H 0.731625 0.349389 0.427607 0.073 Uiso 1 1 calc GR . . . .
H3B H 0.504203 0.327257 0.413903 0.073 Uiso 1 1 calc GR . . . .
H3C H 0.579798 0.400491 0.465653 0.073 Uiso 1 1 calc GR . . . .
C1 C 0.4926(10) 0.7942(4) 0.4395(3) 0.0705(17) Uani 1 1 d . . . . .
H1A H 0.462545 0.851913 0.420544 0.106 Uiso 1 1 calc GR . . . .
H1B H 0.614956 0.797103 0.468609 0.106 Uiso 1 1 calc GR . . . .
H1C H 0.387156 0.775909 0.463696 0.106 Uiso 1 1 calc GR . . . .
C7 C 0.5290(12) 0.3897(5) 0.1291(4) 0.092(3) Uani 1 1 d . . . . .
H7A H 0.516120 0.418257 0.086818 0.138 Uiso 1 1 calc GR . . . .
H7B H 0.419480 0.349625 0.130968 0.138 Uiso 1 1 calc GR . . . .
H7C H 0.651480 0.356840 0.135551 0.138 Uiso 1 1 calc GR . . . .
C5 C 0.0090(8) 0.7311(4) 0.2204(3) 0.0612(16) Uani 1 1 d . . . . .
H5A H -0.120050 0.730485 0.194984 0.092 Uiso 1 1 calc GR . . . .
H5B H 0.108976 0.721930 0.191793 0.092 Uiso 1 1 calc GR . . . .
H5C H 0.030258 0.787624 0.242098 0.092 Uiso 1 1 calc GR . . . .
C9 C 0.5006(14) 0.6530(5) 0.0754(3) 0.097(3) Uani 1 1 d . . . . .
H9A H 0.382011 0.619078 0.062699 0.146 Uiso 1 1 calc GR . . . .
H9B H 0.608422 0.613353 0.089816 0.146 Uiso 1 1 calc GR . . . .
H9C H 0.532585 0.687148 0.038555 0.146 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
Cm1 O4 2.557(3) . ?
Cm1 O1 2.551(3) . ?
Cm1 O6 2.391(3) 1_655 ?
Cm1 O3 2.548(3) . ?
Cm1 O5 2.407(3) . ?
Cm1 O8 2.534(3) . ?
Cm1 O2 2.558(3) . ?
Cm1 O9 2.348(3) . ?
Cm1 O7 2.523(3) . ?
Cm1 C4 2.922(4) . ?
Cm1 C2 2.933(4) . ?
Cm1 C8 2.904(5) . ?
O4 C4 1.249(5) . ?
O10 C10 1.238(5) . ?
O1 C2 1.237(5) . ?
O6 C6 1.241(4) . ?
O3 C4 1.254(5) . ?
O5 C6 1.241(4) . ?
O8 C8 1.260(6) . ?
O2 C2 1.268(5) . ?
O9 C10 1.250(5) . ?
O7 C8 1.257(6) . ?
C4 C3 1.498(6) . ?
C6 C5 1.487(6) . ?
C10 C9 1.480(8) . ?
C2 C1 1.487(6) . ?
C8 C7 1.502(8) . ?

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
O4 Cm1 O2 71.91(10) . . ?
O4 Cm1 C4 25.23(10) . . ?
O4 Cm1 C2 94.53(11) . . ?
O4 Cm1 C8 82.57(13) . . ?
O1 Cm1 O4 116.68(10) . . ?
O1 Cm1 O2 50.38(9) . . ?
O1 Cm1 C4 119.94(10) . . ?
O1 Cm1 C2 24.84(10) . . ?
O1 Cm1 C8 156.87(12) . . ?
O6 Cm1 O4 122.43(10) 1_655 . ?
O6 Cm1 O1 78.62(11) 1_655 . ?
O6 Cm1 O3 73.46(10) 1_655 . ?
O6 Cm1 O5 152.80(12) 1_655 . ?
O6 Cm1 O8 77.02(11) 1_655 . ?
O6 Cm1 O2 83.42(11) 1_655 . ?
O6 Cm1 O7 127.99(11) 1_655 . ?
O6 Cm1 C4 97.56(11) 1_655 . ?
O6 Cm1 C2 80.43(11) 1_655 . ?
O6 Cm1 C8 102.56(13) 1_655 . ?
O3 Cm1 O4 50.41(9) . . ?
O3 Cm1 O1 120.65(10) . . ?
O3 Cm1 O2 74.94(10) . . ?
O3 Cm1 C4 25.33(10) . . ?
O3 Cm1 C2 98.42(11) . . ?
O3 Cm1 C8 81.08(12) . . ?
O5 Cm1 O4 72.42(10) . . ?
O5 Cm1 O1 74.20(12) . . ?
O5 Cm1 O3 122.12(10) . . ?
O5 Cm1 O8 127.44(12) . . ?
O5 Cm1 O2 80.24(12) . . ?
O5 Cm1 O7 76.57(12) . . ?
O5 Cm1 C4 96.91(11) . . ?
O5 Cm1 C2 75.44(12) . . ?
O5 Cm1 C8 101.97(14) . . ?
O8 Cm1 O4 94.18(11) . . ?
O8 Cm1 O1 147.82(11) . . ?
O8 Cm1 O3 71.40(11) . . ?
O8 Cm1 O2 144.64(10) . . ?
O8 Cm1 C4 84.03(11) . . ?
O8 Cm1 C2 157.09(11) . . ?
O8 Cm1 C8 25.66(12) . . ?
O2 Cm1 C4 69.57(10) . . ?
O2 Cm1 C2 25.55(10) . . ?
O2 Cm1 C8 152.53(12) . . ?
O9 Cm1 O4 149.58(11) . . ?
O9 Cm1 O1 76.77(11) . . ?
O9 Cm1 O6 85.91(11) . 1_655 ?
O9 Cm1 O3 148.31(11) . . ?
O9 Cm1 O5 86.81(11) . . ?
O9 Cm1 O8 80.82(12) . . ?
O9 Cm1 O2 127.15(11) . . ?
O9 Cm1 O7 81.73(12) . . ?
O9 Cm1 C4 163.28(12) . . ?
O9 Cm1 C2 101.61(12) . . ?
O9 Cm1 C8 80.26(13) . . ?
O7 Cm1 O4 72.13(11) . . ?
O7 Cm1 O1 144.38(11) . . ?
O7 Cm1 O3 92.13(13) . . ?
O7 Cm1 O8 51.22(11) . . ?
O7 Cm1 O2 141.62(11) . . ?
O7 Cm1 C4 83.28(12) . . ?
O7 Cm1 C2 151.56(12) . . ?
O7 Cm1 C8 25.56(12) . . ?
C4 Cm1 C2 95.10(11) . . ?
C8 Cm1 C4 83.02(13) . . ?
C8 Cm1 C2 176.63(13) . . ?
C4 O4 Cm1 94.0(2) . . ?
C2 O1 Cm1 95.1(3) . . ?
C6 O6 Cm1 146.5(3) . 1_455 ?
C4 O3 Cm1 94.2(2) . . ?
C6 O5 Cm1 153.5(3) . . ?
C8 O8 Cm1 93.8(3) . . ?
C2 O2 Cm1 94.0(2) . . ?
C10 O9 Cm1 164.8(3) . . ?
C8 O7 Cm1 94.5(3) . . ?
O4 C4 Cm1 60.81(19) . . ?
O4 C4 O3 120.7(3) . . ?
O4 C4 C3 119.7(4) . . ?
O3 C4 Cm1 60.4(2) . . ?
O3 C4 C3 119.7(4) . . ?
C3 C4 Cm1 172.4(3) . . ?
O6 C6 O5 122.8(4) . . ?
O6 C6 C5 117.6(4) . . ?
O5 C6 C5 119.6(4) . . ?
O10 C10 O9 122.6(4) . . ?
O10 C10 C9 118.6(4) . . ?
O9 C10 C9 118.8(5) . . ?
O1 C2 Cm1 60.0(2) . . ?
O1 C2 O2 120.5(4) . . ?
O1 C2 C1 120.9(4) . . ?
O2 C2 Cm1 60.5(2) . . ?
O2 C2 C1 118.6(4) . . ?
C1 C2 Cm1 176.8(4) . . ?
O8 C8 Cm1 60.5(2) . . ?
O8 C8 C7 119.1(5) . . ?
O7 C8 Cm1 60.0(2) . . ?
O7 C8 O8 120.5(4) . . ?
O7 C8 C7 120.4(5) . . ?
C7 C8 Cm1 178.7(5) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.499 0.000 0.500 115.9 29.6 ?
2 0.083 0.500 0.000 115.9 29.6 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_euoac_1nov
_database_code_depnum_ccdc_archive 'CCDC 2016263'
loop_
_audit_author_name
_audit_author_address
'Frankie White'
;Los Alamos National Laboratory
United States of America
;
_audit_update_record             
;
2020-07-14 deposited with the CCDC.	2021-03-17 downloaded from the CCDC.
;
_audit_creation_date             2019-11-26
_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         'Eu C10 H15 Eu O10, 2(N), H2 O + [solvent]'
_chemical_formula_sum            'Eu O11 N2 C10 H17'
_chemical_formula_weight         493.22
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Eu Eu -0.1578 3.6682 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.7137(4)
_cell_length_b                   14.8928(8)
_cell_length_c                   20.2772(12)
_cell_angle_alpha                90
_cell_angle_beta                 97.157(3)
_cell_angle_gamma                90
_cell_volume                     2011.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9862
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.77
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.166
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1227 before and 0.0774 after correction. The Ratio of minimum to maximum transmission is 0.7759. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            achromatic
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rectangular blocks'
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0898
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            63722
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.213
_diffrn_reflns_theta_min         1.701
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4184
_reflns_number_total             4950
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.158
_refine_diff_density_min         -2.541
_refine_diff_density_rms         0.223
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         4950
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0584
_refine_ls_restrained_S_all      1.181
_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)+38.3629P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1241
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Idealised Me refined as rotating group:
 C00H(H00A,H00B,H00C), C00L(H00D,H00E,H00F), C00M(H00G,H00H,H00I), C00O(H00J,
 H00K,H00L), C00P(H00M,H00N,H00O)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu01 Eu 0.52948(5) 0.59395(2) 0.78336(2) 0.01025(10) Uani 1 1 d . . . . .
O002 O -0.1352(8) 0.6445(4) 0.7993(3) 0.0161(11) Uani 1 1 d . . . . .
O004 O 0.7301(8) 0.4757(4) 0.8503(3) 0.0178(12) Uani 1 1 d . . . . .
O006 O 0.4035(8) 0.4647(4) 0.8480(3) 0.0174(12) Uani 1 1 d . . . . .
O007 O 0.4947(8) 0.6806(4) 0.6874(3) 0.0193(12) Uani 1 1 d . . . . .
O008 O 0.1803(8) 0.6147(4) 0.7870(3) 0.0174(12) Uani 1 1 d . . . . .
O00A O 0.4935(8) 0.7517(3) 0.8268(3) 0.0160(11) Uani 1 1 d . . . . .
O00B O 0.3704(9) 0.4826(4) 0.7010(3) 0.0273(14) Uani 1 1 d . . . . .
O00C O 0.5280(8) 0.6450(3) 0.9025(3) 0.0165(11) Uani 1 1 d . . . . .
O00E O 0.6973(9) 0.4945(4) 0.7068(3) 0.0227(13) Uani 1 1 d . . . . .
C00F C 0.5770(10) 0.4401(5) 0.8715(4) 0.0118(14) Uani 1 1 d . . . . .
C00G C 0.5351(13) 0.4587(6) 0.6814(4) 0.0219(18) Uani 1 1 d . . . . .
C00H C 0.5350(15) 0.3905(7) 0.6265(5) 0.041(3) Uani 1 1 d . . . . .
H00A H 0.472470 0.336213 0.638984 0.061 Uiso 1 1 calc GR . . . .
H00B H 0.670737 0.378088 0.619076 0.061 Uiso 1 1 calc GR . . . .
H00C H 0.461805 0.413887 0.586483 0.061 Uiso 1 1 calc GR . . . .
C00I C 0.5037(11) 0.7277(5) 0.8870(4) 0.0150(15) Uani 1 1 d . . . . .
C00J C 0.4653(11) 0.7091(5) 0.6288(4) 0.0163(16) Uani 1 1 d . . . . .
C00K C 0.0199(11) 0.6586(5) 0.7717(4) 0.0123(15) Uani 1 1 d . . . . .
C00L C 0.6045(12) 0.3693(5) 0.9245(4) 0.0177(16) Uani 1 1 d . . . . .
H00D H 0.732203 0.340499 0.923828 0.027 Uiso 1 1 calc GR . . . .
H00E H 0.499376 0.325486 0.916511 0.027 Uiso 1 1 calc GR . . . .
H00F H 0.599652 0.396540 0.967215 0.027 Uiso 1 1 calc GR . . . .
C00M C 0.4882(14) 0.7960(6) 0.9403(4) 0.0266(19) Uani 1 1 d . . . . .
H00G H 0.482964 0.855048 0.921113 0.040 Uiso 1 1 calc GR . . . .
H00H H 0.603199 0.791421 0.973330 0.040 Uiso 1 1 calc GR . . . .
H00I H 0.368444 0.785396 0.960489 0.040 Uiso 1 1 calc GR . . . .
C00O C 0.0265(17) 0.7391(8) 0.7227(7) 0.056(4) Uani 1 1 d . . . . .
H00J H -0.107874 0.758325 0.707495 0.085 Uiso 1 1 calc GR . . . .
H00K H 0.091471 0.720584 0.685384 0.085 Uiso 1 1 calc GR . . . .
H00L H 0.099969 0.787890 0.745112 0.085 Uiso 1 1 calc GR . . . .
C00P C 0.503(2) 0.6488(8) 0.5736(5) 0.055(4) Uani 1 1 d . . . . .
H00M H 0.623360 0.615243 0.586064 0.083 Uiso 1 1 calc GR . . . .
H00N H 0.516684 0.683960 0.534740 0.083 Uiso 1 1 calc GR . . . .
H00O H 0.391582 0.608228 0.564138 0.083 Uiso 1 1 calc GR . . . .
N3 N 1.0931(10) 0.5427(5) 0.9158(3) 0.0195(15) Uani 1 1 d . . . . .
O1 O 0.3458(8) 0.8835(4) 0.5025(3) 0.0183(12) Uani 1 1 d . . . . .
H1A H 0.368200 0.851589 0.537419 0.027 Uiso 1 1 d G . . . .
H1B H 0.258380 0.854166 0.477329 0.027 Uiso 1 1 d G . . . .
N1 N 0.4544(9) 0.8912(4) 0.7327(3) 0.0159(14) Uani 1 1 d . . . . .
O009 O 0.4095(9) 0.7889(4) 0.6154(3) 0.0244(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Eu01 O002 2.357(5) 1_655 ?
Eu01 O004 2.510(5) . ?
Eu01 O006 2.533(6) . ?
Eu01 O007 2.323(5) . ?
Eu01 O008 2.375(5) . ?
Eu01 O00A 2.530(5) . ?
Eu01 O00B 2.497(6) . ?
Eu01 O00C 2.534(5) . ?
Eu01 O00E 2.512(6) . ?
Eu01 C00F 2.899(7) . ?
Eu01 C00G 2.890(8) . ?
Eu01 C00I 2.916(8) . ?
O002 C00K 1.259(9) . ?
O004 C00F 1.278(9) . ?
O006 C00F 1.257(9) . ?
O007 C00J 1.254(9) . ?
O008 C00K 1.265(9) . ?
O00A C00I 1.267(9) . ?
O00B C00G 1.271(10) . ?
O00C C00I 1.276(9) . ?
O00E C00G 1.263(10) . ?
C00F C00L 1.501(10) . ?
C00G C00H 1.506(12) . ?
C00I C00M 1.497(11) . ?
C00J C00P 1.480(12) . ?
C00J O009 1.266(9) . ?
C00K C00O 1.561(13) . ?

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
O002 Eu01 O004 73.20(18) 1_655 . ?
O002 Eu01 O006 123.13(18) 1_655 . ?
O002 Eu01 O008 152.07(19) 1_655 . ?
O002 Eu01 O00A 77.69(18) 1_655 . ?
O002 Eu01 O00B 128.70(19) 1_655 . ?
O002 Eu01 O00C 83.72(18) 1_655 . ?
O002 Eu01 O00E 77.22(19) 1_655 . ?
O002 Eu01 C00F 97.94(19) 1_655 . ?
O002 Eu01 C00G 102.9(2) 1_655 . ?
O002 Eu01 C00I 79.90(19) 1_655 . ?
O004 Eu01 O006 51.56(17) . . ?
O004 Eu01 O00A 122.08(18) . . ?
O004 Eu01 O00C 76.15(18) . . ?
O004 Eu01 O00E 70.66(19) . . ?
O004 Eu01 C00F 26.08(18) . . ?
O004 Eu01 C00G 81.0(2) . . ?
O004 Eu01 C00I 99.5(2) . . ?
O006 Eu01 O00C 72.16(17) . . ?
O006 Eu01 C00F 25.63(18) . . ?
O006 Eu01 C00G 82.8(2) . . ?
O006 Eu01 C00I 95.3(2) . . ?
O007 Eu01 O002 86.10(19) . 1_655 ?
O007 Eu01 O004 146.52(18) . . ?
O007 Eu01 O006 148.29(19) . . ?
O007 Eu01 O008 87.55(18) . . ?
O007 Eu01 O00A 76.79(19) . . ?
O007 Eu01 O00B 79.6(2) . . ?
O007 Eu01 O00C 128.32(19) . . ?
O007 Eu01 O00E 79.4(2) . . ?
O007 Eu01 C00F 161.4(2) . . ?
O007 Eu01 C00G 78.3(2) . . ?
O007 Eu01 C00I 102.4(2) . . ?
O008 Eu01 O004 122.67(17) . . ?
O008 Eu01 O006 71.85(17) . . ?
O008 Eu01 O00A 74.38(18) . . ?
O008 Eu01 O00B 76.5(2) . . ?
O008 Eu01 O00C 79.04(18) . . ?
O008 Eu01 O00E 128.08(19) . . ?
O008 Eu01 C00F 96.71(19) . . ?
O008 Eu01 C00G 102.4(2) . . ?
O008 Eu01 C00I 75.0(2) . . ?
O00A Eu01 O006 118.24(18) . . ?
O00A Eu01 O00C 51.53(17) . . ?
O00A Eu01 C00F 121.81(19) . . ?
O00A Eu01 C00G 155.0(2) . . ?
O00A Eu01 C00I 25.66(19) . . ?
O00B Eu01 O004 93.0(2) . . ?
O00B Eu01 O006 72.45(19) . . ?
O00B Eu01 O00A 142.9(2) . . ?
O00B Eu01 O00C 141.69(18) . . ?
O00B Eu01 O00E 51.86(19) . . ?
O00B Eu01 C00F 83.8(2) . . ?
O00B Eu01 C00G 26.0(2) . . ?
O00B Eu01 C00I 151.2(2) . . ?
O00C Eu01 C00F 70.28(19) . . ?
O00C Eu01 C00G 153.3(2) . . ?
O00C Eu01 C00I 25.88(19) . . ?
O00E Eu01 O006 94.35(19) . . ?
O00E Eu01 O00A 146.30(19) . . ?
O00E Eu01 O00C 145.25(18) . . ?
O00E Eu01 C00F 83.8(2) . . ?
O00E Eu01 C00G 25.8(2) . . ?
O00E Eu01 C00I 156.88(19) . . ?
C00F Eu01 C00I 96.2(2) . . ?
C00G Eu01 C00F 83.1(2) . . ?
C00G Eu01 C00I 177.2(2) . . ?
C00K O002 Eu01 145.2(5) . 1_455 ?
C00F O004 Eu01 94.2(4) . . ?
C00F O006 Eu01 93.7(4) . . ?
C00J O007 Eu01 165.8(6) . . ?
C00K O008 Eu01 150.8(5) . . ?
C00I O00A Eu01 94.4(5) . . ?
C00G O00B Eu01 94.5(5) . . ?
C00I O00C Eu01 94.0(5) . . ?
C00G O00E Eu01 94.0(5) . . ?
O004 C00F Eu01 59.7(4) . . ?
O004 C00F C00L 120.0(7) . . ?
O006 C00F Eu01 60.7(4) . . ?
O006 C00F O004 119.8(7) . . ?
O006 C00F C00L 120.1(7) . . ?
C00L C00F Eu01 172.4(5) . . ?
O00B C00G Eu01 59.5(4) . . ?
O00B C00G C00H 119.9(8) . . ?
O00E C00G Eu01 60.1(4) . . ?
O00E C00G O00B 119.6(8) . . ?
O00E C00G C00H 120.4(8) . . ?
C00H C00G Eu01 178.1(7) . . ?
O00A C00I Eu01 59.9(4) . . ?
O00A C00I O00C 120.0(7) . . ?
O00A C00I C00M 120.2(7) . . ?
O00C C00I Eu01 60.1(4) . . ?
O00C C00I C00M 119.8(7) . . ?
C00M C00I Eu01 179.4(6) . . ?
O007 C00J C00P 119.4(8) . . ?
O007 C00J O009 121.9(8) . . ?
O009 C00J C00P 118.7(8) . . ?
O002 C00K O008 122.1(7) . . ?
O002 C00K C00O 120.1(8) . . ?
O008 C00K C00O 117.5(7) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 0.500 102.8 30.9 ?
2 0.500 0.000 0.000 102.8 30.9 ?

_olex2_submission_special_instructions 'No special instructions were received'
