# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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. 
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#######################################################################

data_ada205
_database_code_depnum_ccdc_archive 'CCDC 2104590'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2021-08-21 deposited with the CCDC.	2022-12-15 downloaded from the CCDC.
;
_audit_creation_date             2019-07-17
_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         'C6 H14 N7 Nd O10'
_chemical_formula_sum            'C6 H14 N7 Nd O10'
_chemical_formula_weight         488.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nd Nd -3.1807 10.9079 '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           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                   11.9718(3)
_cell_length_b                   6.8227(2)
_cell_length_c                   16.7881(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.460(1)
_cell_angle_gamma                90
_cell_volume                     1368.75(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.098
_cell_measurement_theta_min      4.413
_shelx_estimated_absorpt_T_max   0.470
_shelx_estimated_absorpt_T_min   0.071
_exptl_absorpt_coefficient_mu    29.691
_exptl_absorpt_correction_T_max  0.1120
_exptl_absorpt_correction_T_min  0.0126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1211 before and 0.0619 after correction. The Ratio of minimum to maximum transmission is 0.1125. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             956
_exptl_crystal_recrystallization_method 'crystallized from H2O / DMSO / iPrOH'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            33824
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.114
_diffrn_reflns_theta_min         4.413
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2582
_reflns_number_total             2605
_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       
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2605
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0227
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+0.2696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0607
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O4(H4A,H4B), O5(H5A,H5B), O6(H6A,H6B), O7(H7A,H7B), O8(H8A,H8B), O9(H9A,H9B),
 O10(H10A,H10B)
;
_atom_sites_solution_hydrogens   difmap
_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
Nd1 Nd 0.51721(2) 0.36376(2) 0.17606(2) 0.02556(8) Uani 1 1 d . . . . .
O1 O 0.66465(14) 0.2289(3) 0.27289(10) 0.0321(4) Uani 1 1 d . . . . .
O2 O 0.18057(15) 0.4083(3) 0.45232(11) 0.0298(4) Uani 1 1 d . . . . .
O3 O 0.65001(16) 0.1456(2) 0.67659(12) 0.0304(4) Uani 1 1 d . . . . .
O4 O 0.39707(15) 0.0764(3) 0.19857(11) 0.0328(4) Uani 1 1 d . . . . .
H4A H 0.392910 0.015245 0.244677 0.049 Uiso 1 1 d GR . . . .
H4B H 0.355234 0.011930 0.162156 0.049 Uiso 1 1 d GR . . . .
O5 O 0.60329(17) 0.6561(3) 0.24681(12) 0.0331(4) Uani 1 1 d . . . . .
H5A H 0.586967 0.684135 0.295955 0.050 Uiso 1 1 d GR . . . .
H5B H 0.675436 0.682677 0.248793 0.050 Uiso 1 1 d GR . . . .
O6 O 0.34826(14) 0.5498(3) 0.20238(11) 0.0321(4) Uani 1 1 d . . . . .
H6A H 0.288700 0.474978 0.194649 0.048 Uiso 1 1 d GR . . . .
H6B H 0.349181 0.623656 0.245434 0.048 Uiso 1 1 d GR . . . .
O7 O 0.49978(16) 0.6587(3) 0.08379(12) 0.0302(4) Uani 1 1 d . . . . .
H7A H 0.537136 0.658121 0.040252 0.045 Uiso 1 1 d GR . . . .
H7B H 0.435354 0.715357 0.070430 0.045 Uiso 1 1 d GR . . . .
O8 O 0.38702(14) 0.2927(3) 0.05423(10) 0.0303(3) Uani 1 1 d . . . . .
H8A H 0.371571 0.166553 0.053568 0.045 Uiso 1 1 d GR . . . .
H8B H 0.317778 0.336380 0.053770 0.045 Uiso 1 1 d GR . . . .
O9 O 0.68289(15) 0.4149(3) 0.10590(11) 0.0315(4) Uani 1 1 d . . . . .
H9A H 0.718609 0.527004 0.102302 0.047 Uiso 1 1 d GR . . . .
H9B H 0.726661 0.317284 0.093344 0.047 Uiso 1 1 d GR . . . .
O10 O 0.58351(15) 0.0619(3) 0.10440(11) 0.0347(4) Uani 1 1 d . . . . .
H10A H 0.569491 -0.058203 0.120764 0.052 Uiso 1 1 d GR . . . .
H10B H 0.616629 0.064216 0.058784 0.052 Uiso 1 1 d GR . . . .
N1 N 0.50574(18) 0.3046(4) 0.32848(12) 0.0288(4) Uani 1 1 d . . . . .
N2 N 0.3400(2) 0.3678(3) 0.38794(15) 0.0291(5) Uani 1 1 d . . . . .
N3 N 0.66978(16) 0.2022(3) 0.40784(12) 0.0284(4) Uani 1 1 d . . . . .
N4 N 0.49937(16) 0.2635(3) 0.46722(12) 0.0278(4) Uani 1 1 d . . . . .
N5 N 0.33201(18) 0.3189(3) 0.53026(13) 0.0293(4) Uani 1 1 d . . . . .
N6 N 0.66068(19) 0.1589(3) 0.54299(14) 0.0283(4) Uani 1 1 d . . . . .
N7 N 0.48886(17) 0.2241(3) 0.60651(12) 0.0287(4) Uani 1 1 d . . . . .
C1 C 0.6147(2) 0.2449(4) 0.33687(15) 0.0284(5) Uani 1 1 d . . . . .
C2 C 0.4461(2) 0.3132(4) 0.39317(15) 0.0279(5) Uani 1 1 d . . . . .
C3 C 0.2844(2) 0.3644(3) 0.45631(17) 0.0276(5) Uani 1 1 d . . . . .
C4 C 0.6120(2) 0.2074(4) 0.47271(15) 0.0278(5) Uani 1 1 d . . . . .
C5 C 0.4390(2) 0.2683(3) 0.53567(14) 0.0278(5) Uani 1 1 d . . . . .
C6 C 0.6002(2) 0.1766(4) 0.60961(15) 0.0277(5) 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
Nd1 O1 2.5017(17) . ?
Nd1 O4 2.4740(18) . ?
Nd1 O5 2.5107(19) . ?
Nd1 O6 2.4507(17) . ?
Nd1 O7 2.5401(18) . ?
Nd1 O8 2.5422(17) . ?
Nd1 O9 2.3926(18) . ?
Nd1 O10 2.5367(18) . ?
Nd1 N1 2.602(2) . ?
Nd1 C1 2.988(2) . ?
O1 C1 1.265(3) . ?
O2 C3 1.277(3) . ?
O3 C6 1.259(3) . ?
O4 H4A 0.8835 . ?
O4 H4B 0.8838 . ?
O5 H5A 0.8802 . ?
O5 H5B 0.8812 . ?
O6 H6A 0.8803 . ?
O6 H6B 0.8806 . ?
O7 H7A 0.8796 . ?
O7 H7B 0.8797 . ?
O8 H8A 0.8803 . ?
O8 H8B 0.8805 . ?
O9 H9A 0.8804 . ?
O9 H9B 0.8806 . ?
O10 H10A 0.8833 . ?
O10 H10B 0.8836 . ?
N1 C1 1.366(3) . ?
N1 C2 1.336(3) . ?
N2 C2 1.321(3) . ?
N2 C3 1.361(4) . ?
N3 C1 1.358(3) . ?
N3 C4 1.325(3) . ?
N4 C2 1.404(3) . ?
N4 C4 1.400(3) . ?
N4 C5 1.394(3) . ?
N5 C3 1.370(4) . ?
N5 C5 1.325(3) . ?
N6 C4 1.326(3) . ?
N6 C6 1.374(4) . ?
N7 C5 1.333(3) . ?
N7 C6 1.370(3) . ?

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 Nd1 O5 74.42(7) . . ?
O1 Nd1 O7 135.75(6) . . ?
O1 Nd1 O8 145.79(6) . . ?
O1 Nd1 O10 77.34(6) . . ?
O1 Nd1 N1 51.76(6) . . ?
O1 Nd1 C1 24.66(6) . . ?
O4 Nd1 O1 90.18(6) . . ?
O4 Nd1 O5 141.54(6) . . ?
O4 Nd1 O7 133.93(6) . . ?
O4 Nd1 O8 68.77(6) . . ?
O4 Nd1 O10 68.31(6) . . ?
O4 Nd1 N1 70.19(7) . . ?
O4 Nd1 C1 81.14(6) . . ?
O5 Nd1 O7 71.06(7) . . ?
O5 Nd1 O8 138.28(6) . . ?
O5 Nd1 O10 137.58(6) . . ?
O5 Nd1 N1 72.70(7) . . ?
O5 Nd1 C1 70.21(7) . . ?
O6 Nd1 O1 129.12(6) . . ?
O6 Nd1 O4 83.64(6) . . ?
O6 Nd1 O5 79.79(6) . . ?
O6 Nd1 O7 70.20(6) . . ?
O6 Nd1 O8 76.77(6) . . ?
O6 Nd1 O10 142.31(6) . . ?
O6 Nd1 N1 79.05(7) . . ?
O6 Nd1 C1 105.04(6) . . ?
O7 Nd1 O8 68.70(6) . . ?
O7 Nd1 N1 135.67(7) . . ?
O7 Nd1 C1 141.19(6) . . ?
O8 Nd1 N1 134.05(6) . . ?
O8 Nd1 C1 149.57(6) . . ?
O9 Nd1 O1 78.47(6) . . ?
O9 Nd1 O4 134.23(6) . . ?
O9 Nd1 O5 77.78(7) . . ?
O9 Nd1 O6 136.97(6) . . ?
O9 Nd1 O7 67.94(6) . . ?
O9 Nd1 O8 96.78(6) . . ?
O9 Nd1 O10 65.95(6) . . ?
O9 Nd1 N1 126.95(7) . . ?
O9 Nd1 C1 101.18(7) . . ?
O10 Nd1 O7 111.75(6) . . ?
O10 Nd1 O8 69.99(6) . . ?
O10 Nd1 N1 112.14(7) . . ?
O10 Nd1 C1 95.26(6) . . ?
N1 Nd1 C1 27.18(7) . . ?
C1 O1 Nd1 99.74(14) . . ?
Nd1 O4 H4A 124.9 . . ?
Nd1 O4 H4B 126.8 . . ?
H4A O4 H4B 108.1 . . ?
Nd1 O5 H5A 120.5 . . ?
Nd1 O5 H5B 123.7 . . ?
H5A O5 H5B 101.1 . . ?
Nd1 O6 H6A 110.1 . . ?
Nd1 O6 H6B 118.3 . . ?
H6A O6 H6B 115.0 . . ?
Nd1 O7 H7A 118.4 . . ?
Nd1 O7 H7B 122.8 . . ?
H7A O7 H7B 105.8 . . ?
Nd1 O8 H8A 108.3 . . ?
Nd1 O8 H8B 118.3 . . ?
H8A O8 H8B 97.7 . . ?
Nd1 O9 H9A 125.5 . . ?
Nd1 O9 H9B 122.1 . . ?
H9A O9 H9B 110.0 . . ?
Nd1 O10 H10A 122.3 . . ?
Nd1 O10 H10B 124.5 . . ?
H10A O10 H10B 113.0 . . ?
C1 N1 Nd1 92.34(14) . . ?
C2 N1 Nd1 148.73(18) . . ?
C2 N1 C1 118.9(2) . . ?
C2 N2 C3 117.1(2) . . ?
C4 N3 C1 117.8(2) . . ?
C4 N4 C2 120.6(2) . . ?
C5 N4 C2 119.6(2) . . ?
C5 N4 C4 119.8(2) . . ?
C5 N5 C3 117.9(2) . . ?
C4 N6 C6 118.5(2) . . ?
C5 N7 C6 118.0(2) . . ?
O1 C1 Nd1 55.60(12) . . ?
O1 C1 N1 115.8(2) . . ?
O1 C1 N3 119.8(2) . . ?
N1 C1 Nd1 60.48(12) . . ?
N3 C1 Nd1 173.42(17) . . ?
N3 C1 N1 124.3(2) . . ?
N1 C2 N4 118.2(2) . . ?
N2 C2 N1 121.1(2) . . ?
N2 C2 N4 120.7(2) . . ?
O2 C3 N2 118.4(2) . . ?
O2 C3 N5 116.8(2) . . ?
N2 C3 N5 124.8(2) . . ?
N3 C4 N4 120.1(2) . . ?
N3 C4 N6 120.1(2) . . ?
N6 C4 N4 119.8(2) . . ?
N5 C5 N4 119.8(2) . . ?
N5 C5 N7 119.9(2) . . ?
N7 C5 N4 120.3(2) . . ?
O3 C6 N6 117.9(2) . . ?
O3 C6 N7 118.8(2) . . ?
N7 C6 N6 123.3(2) . . ?

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
_geom_hbond_publ_flag
O4 H4A O3 0.88 1.82 2.674(3) 163.1 3_656 yes
O4 H4B O2 0.88 2.07 2.883(3) 152.9 2_545 yes
O4 H4B N2 0.88 2.63 3.420(3) 149.8 2_545 yes
O5 H5A N7 0.88 2.02 2.877(3) 164.5 3_666 yes
O5 H5B O1 0.88 2.00 2.861(3) 167.1 2_655 yes
O6 H6A O3 0.88 1.86 2.734(3) 170.8 4_565 yes
O6 H6B O3 0.88 2.05 2.905(3) 164.6 3_666 yes
O7 H7A O8 0.88 1.90 2.774(3) 169.5 3_665 yes
O7 H7B O2 0.88 1.93 2.788(3) 163.2 2 yes
O8 H8A O2 0.88 1.87 2.745(3) 172.4 2_545 yes
O8 H8B N6 0.88 1.88 2.725(3) 160.6 4_565 yes
O9 H9A N3 0.88 1.81 2.656(3) 161.0 2_655 yes
O9 H9B N5 0.88 1.93 2.760(3) 155.8 4_665 yes
O10 H10A O7 0.88 2.18 2.941(3) 144.1 1_545 yes
O10 H10B O2 0.88 2.00 2.875(3) 174.1 4_665 yes

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
Nd1 O1 C1 N1 6.0(2) . . . . ?
Nd1 O1 C1 N3 -174.4(2) . . . . ?
Nd1 N1 C1 O1 -5.7(2) . . . . ?
Nd1 N1 C1 N3 174.7(2) . . . . ?
Nd1 N1 C2 N2 4.3(5) . . . . ?
Nd1 N1 C2 N4 -175.5(2) . . . . ?
C1 N1 C2 N2 -179.2(2) . . . . ?
C1 N1 C2 N4 1.1(4) . . . . ?
C1 N3 C4 N4 -2.7(3) . . . . ?
C1 N3 C4 N6 177.2(2) . . . . ?
C2 N1 C1 Nd1 -178.2(3) . . . . ?
C2 N1 C1 O1 176.1(2) . . . . ?
C2 N1 C1 N3 -3.5(4) . . . . ?
C2 N2 C3 O2 -177.1(2) . . . . ?
C2 N2 C3 N5 3.7(3) . . . . ?
C2 N4 C4 N3 0.5(3) . . . . ?
C2 N4 C4 N6 -179.3(2) . . . . ?
C2 N4 C5 N5 0.3(3) . . . . ?
C2 N4 C5 N7 -179.1(2) . . . . ?
C3 N2 C2 N1 177.3(2) . . . . ?
C3 N2 C2 N4 -3.0(3) . . . . ?
C3 N5 C5 N4 0.2(3) . . . . ?
C3 N5 C5 N7 179.6(2) . . . . ?
C4 N3 C1 O1 -175.3(2) . . . . ?
C4 N3 C1 N1 4.3(4) . . . . ?
C4 N4 C2 N1 0.3(3) . . . . ?
C4 N4 C2 N2 -179.5(2) . . . . ?
C4 N4 C5 N5 -179.1(2) . . . . ?
C4 N4 C5 N7 1.6(3) . . . . ?
C4 N6 C6 O3 -174.3(2) . . . . ?
C4 N6 C6 N7 6.4(4) . . . . ?
C5 N4 C2 N1 -179.1(2) . . . . ?
C5 N4 C2 N2 1.2(3) . . . . ?
C5 N4 C4 N3 179.9(2) . . . . ?
C5 N4 C4 N6 0.0(3) . . . . ?
C5 N5 C3 O2 178.5(2) . . . . ?
C5 N5 C3 N2 -2.3(4) . . . . ?
C5 N7 C6 O3 175.9(2) . . . . ?
C5 N7 C6 N6 -4.7(4) . . . . ?
C6 N6 C4 N3 176.4(2) . . . . ?
C6 N6 C4 N4 -3.8(3) . . . . ?
C6 N7 C5 N4 0.7(3) . . . . ?
C6 N7 C5 N5 -178.6(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_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_ada2263
_database_code_depnum_ccdc_archive 'CCDC 2104591'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2021-12-19 deposited with the CCDC.	2022-12-15 downloaded from the CCDC.
;
_vrf_PLAT094_ada2263             
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.04 Report
RESPONSE:

 The ratio of the maximum and minimum residual density excursions is
 unusual. This might indicate unaccounted for twinning or missing atoms 
 (e.g. associated with disordered solvent). 

All residual density peaks above 1 electron are located in the vicinity
of the Nd atoms, so they don't correspond to missing atoms. Also the crystal
has been refined as an inversion twin.
;



_audit_creation_date             2019-10-16
_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         'C6 H4 N7 Nd O5, 2(H2 O)'
_chemical_formula_sum            'C6 H8 N7 Nd O7'
_chemical_formula_weight         434.43
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nd Nd -3.1807 10.9079 '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      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.4684(3)
_cell_length_b                   12.9539(3)
_cell_length_c                   20.1278(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2990.20(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9885
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.081
_cell_measurement_theta_min      5.151
_shelx_estimated_absorpt_T_max   0.222
_shelx_estimated_absorpt_T_min   0.222
_exptl_absorpt_coefficient_mu    26.937
_exptl_absorpt_correction_T_max  0.2558
_exptl_absorpt_correction_T_min  0.1397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1623 before and 0.0468 after correction. The Ratio of minimum to maximum transmission is 0.5461. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.930
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       octahedron
_exptl_crystal_F_000             1672
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            31026
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.075
_diffrn_reflns_theta_min         4.393
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2816
_reflns_number_total             2845
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         2.554
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.242
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.493(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2845
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.129
_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)+(0.0886P)²+1.7862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1080
_refine_special_details          'Refined as a 2-component inversion twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.507(14)
 0.493(14)
2. Fixed Uiso
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
3. Uiso/Uaniso restraints and constraints
O6A \\sim O6B \\sim O7A \\sim O7B \\sim O7C \\sim O8A \\sim O8B \\sim O8C:
within 2.6A with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: O6A(0.25) H6AA(0.25) H6AB(0.25) O6B(0.25) H6B(0.5) O7A(0.25)
 H7AA(0.25) H7AB(0.25) O7B(0.25) H7BA(0.25) H7BB(0.25) O7C(0.25) H7CA(0.25)
 H7CB(0.25) O8A(0.25) H8A(0.5) O8B(0.25) H8BA(0.25) H8BB(0.25) O8C(0.25)
 H8CA(0.25) H8CB(0.25)
5.a Riding coordinates:
 O4(H4A,H4B), O5(H5A,H5B), O6A(H6AA,H6AB), O6B(H6B), O7A(H7AA,H7AB), O7B(H7BA,
 H7BB), O7C(H7CA,H7CB), O8A(H8A), O8B(H8BA,H8BB), O8C(H8CA,H8CB)
;
_atom_sites_solution_hydrogens   difmap
_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
Nd1 Nd 0.54425(5) 0.500000 0.500000 0.0315(2) Uani 1 2 d S T P . .
Nd2 Nd 0.500000 0.53609(4) 0.750000 0.0318(2) Uani 1 2 d S T P . .
O1 O 0.3989(9) 0.3714(7) 0.4583(4) 0.054(2) Uani 1 1 d . . . . .
O2 O 0.3520(11) 0.4091(10) 0.7909(4) 0.080(4) Uani 1 1 d . . . . .
O3 O 0.0499(5) 0.0407(5) 0.6249(3) 0.0331(11) Uani 1 1 d . . . . .
O4 O 0.6745(12) 0.6055(10) 0.4291(4) 0.075(4) Uani 1 1 d . . . . .
H4A H 0.672068 0.609589 0.385966 0.112 Uiso 1 1 d R . . . .
H4B H 0.715967 0.658499 0.441246 0.112 Uiso 1 1 d R . . . .
O5 O 0.3702(12) 0.6413(10) 0.6792(4) 0.067(3) Uani 1 1 d . . . . .
H5A H 0.356923 0.658536 0.638109 0.101 Uiso 1 1 d R . . . .
H5B H 0.337063 0.689786 0.702439 0.101 Uiso 1 1 d R . . . .
N1 N 0.2667(9) 0.2717(8) 0.6243(4) 0.050(2) Uani 1 1 d . . . . .
N2 N 0.2793(9) 0.2567(8) 0.5078(10) 0.051(3) Uani 1 1 d . . . . .
N3 N 0.3898(10) 0.3833(9) 0.5670(5) 0.049(2) Uani 1 1 d . . . . .
N4 N 0.3749(14) 0.3985(11) 0.6812(5) 0.065(4) Uani 1 1 d . . . . .
N5 N 0.2487(11) 0.2803(9) 0.7418(10) 0.064(4) Uani 1 1 d . . . . .
N6 N 0.1453(12) 0.1604(10) 0.6842(5) 0.054(3) Uani 1 1 d . . . . .
N7 N 0.1653(11) 0.1437(9) 0.5655(4) 0.048(2) Uani 1 1 d . . . . .
C1 C 0.3546(11) 0.3368(9) 0.5105(5) 0.052(3) Uani 1 1 d . . . . .
C2 C 0.3476(10) 0.3546(9) 0.6236(6) 0.052(3) Uani 1 1 d . . . . .
C3 C 0.3243(13) 0.3641(13) 0.7379(5) 0.070(4) Uani 1 1 d . . . . .
C4 C 0.2185(13) 0.2367(11) 0.6853(5) 0.057(3) Uani 1 1 d . . . . .
C5 C 0.1204(9) 0.1150(8) 0.6248(4) 0.0391(19) Uani 1 1 d . . . . .
C6 C 0.2353(11) 0.2239(10) 0.5647(5) 0.050(3) Uani 1 1 d . . . . .
O6A O 0.117(6) 0.525(5) 0.753(6) 0.174(12) Uani 0.25 1 d . U . A 1
H6AA H 0.085987 0.544386 0.716005 0.262 Uiso 0.25 1 d R . . A 1
H6AB H 0.147757 0.465066 0.744755 0.262 Uiso 0.25 1 d R . . A 1
O6B O 0.000000 0.413(5) 0.750000 0.183(13) Uani 0.5 2 d S TU P B 2
H6B H 0.060690 0.373170 0.755810 0.274 Uiso 0.5 1 d R . . B 2
O7A O -0.011(7) 0.618(5) 0.631(5) 0.168(13) Uani 0.25 1 d . U . C 2
H7AA H -0.054997 0.667804 0.616427 0.251 Uiso 0.25 1 d R . . C 2
H7AB H -0.044887 0.587744 0.664267 0.251 Uiso 0.25 1 d R . . C 2
O7B O 0.115(8) 0.579(6) 0.649(6) 0.171(12) Uani 0.25 1 d . U . D 2
H7BA H 0.184572 0.600837 0.658149 0.256 Uiso 0.25 1 d R . . D 2
H7BB H 0.116811 0.567097 0.606049 0.256 Uiso 0.25 1 d R . . D 2
O7C O 0.063(8) 0.655(7) 0.668(5) 0.171(12) Uani 0.25 1 d . U . E 1
H7CA H 0.015235 0.621467 0.689913 0.257 Uiso 0.25 1 d R . . E 1
H7CB H 0.112575 0.690188 0.691703 0.257 Uiso 0.25 1 d R . . E 1
O8A O 0.113(5) 0.500000 0.500000 0.178(13) Uani 0.5 2 d S TU P F 2
H8A H 0.067822 0.474790 0.469540 0.267 Uiso 0.5 1 d R . . F 2
O8B O 0.085(8) 0.442(6) 0.564(5) 0.172(12) Uani 0.25 1 d . U . G 1
H8BA H 0.070075 0.491805 0.591721 0.259 Uiso 0.25 1 d R . . G 1
H8BB H 0.128625 0.396015 0.583591 0.259 Uiso 0.25 1 d R . . G 1
O8C O 0.005(9) 0.385(6) 0.557(6) 0.172(13) Uani 0.25 1 d . U . H 2
H8CA H 0.014995 0.442391 0.577854 0.259 Uiso 0.25 1 d R . . H 2
H8CB H 0.016155 0.400551 0.515074 0.259 Uiso 0.25 1 d R . . H 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Nd1 O1 2.502(8) . ?
Nd1 O1 2.502(8) 4_566 ?
Nd1 O3 2.570(6) 5 ?
Nd1 O3 2.570(6) 8_556 ?
Nd1 O4 2.477(10) 4_566 ?
Nd1 O4 2.477(10) . ?
Nd1 N3 2.691(10) 4_566 ?
Nd1 N3 2.691(10) . ?
Nd1 N7 2.670(10) 8_556 ?
Nd1 N7 2.670(10) 5 ?
Nd1 C1 3.040(11) . ?
Nd1 C1 3.040(10) 4_566 ?
Nd2 O2 2.503(9) 3_656 ?
Nd2 O2 2.503(9) . ?
Nd2 O3 2.582(6) 5 ?
Nd2 O3 2.582(6) 7_556 ?
Nd2 O5 2.471(10) . ?
Nd2 O5 2.471(10) 3_656 ?
Nd2 N4 2.675(11) 3_656 ?
Nd2 N4 2.675(11) . ?
Nd2 N6 2.668(12) 5 ?
Nd2 N6 2.668(12) 7_556 ?
Nd2 C3 3.014(12) . ?
Nd2 C3 3.014(12) 3_656 ?
O1 C1 1.249(14) . ?
O2 C3 1.256(14) . ?
O3 C5 1.258(12) . ?
O4 H4A 0.8697 . ?
O4 H4B 0.8702 . ?
O5 H5A 0.8697 . ?
O5 H5B 0.8701 . ?
N1 C2 1.419(13) . ?
N1 C4 1.421(14) . ?
N1 C6 1.396(13) . ?
N2 C1 1.351(14) . ?
N2 C6 1.32(2) . ?
N3 C1 1.348(15) . ?
N3 C2 1.292(14) . ?
N4 C2 1.329(15) . ?
N4 C3 1.355(15) . ?
N5 C3 1.392(15) . ?
N5 C4 1.32(2) . ?
N6 C4 1.297(18) . ?
N6 C5 1.363(14) . ?
N7 C5 1.352(13) . ?
N7 C6 1.314(16) . ?
O6A H6AA 0.8689 . ?
O6A H6AB 0.8694 . ?
O6B H6B 0.8736 . ?
O6B H6B 0.8736 3_556 ?
O7A H7AA 0.8696 . ?
O7A H7AB 0.8698 . ?
O7B H7BA 0.8698 . ?
O7B H7BB 0.8708 . ?
O7C H7CA 0.8294 . ?
O7C H7CB 0.8705 . ?
O8A H8A 0.8644 . ?
O8A H8A 0.8644 4_566 ?
O8B H8BA 0.8690 . ?
O8B H8BB 0.8702 . ?
O8C H8CA 0.8698 . ?
O8C H8CB 0.8695 . ?

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 Nd1 O1 96.4(5) . 4_566 ?
O1 Nd1 O3 63.4(2) . 8_556 ?
O1 Nd1 O3 118.8(2) 4_566 8_556 ?
O1 Nd1 O3 118.8(2) . 5 ?
O1 Nd1 O3 63.4(2) 4_566 5 ?
O1 Nd1 N3 49.8(3) . . ?
O1 Nd1 N3 76.6(4) . 4_566 ?
O1 Nd1 N3 76.6(4) 4_566 . ?
O1 Nd1 N3 49.8(3) 4_566 4_566 ?
O1 Nd1 N7 167.5(3) . 5 ?
O1 Nd1 N7 73.6(4) 4_566 5 ?
O1 Nd1 N7 73.6(4) . 8_556 ?
O1 Nd1 N7 167.5(3) 4_566 8_556 ?
O1 Nd1 C1 87.9(3) . 4_566 ?
O1 Nd1 C1 23.6(3) . . ?
O1 Nd1 C1 87.9(3) 4_566 . ?
O1 Nd1 C1 23.6(3) 4_566 4_566 ?
O3 Nd1 O3 177.1(3) 8_556 5 ?
O3 Nd1 N3 69.0(2) 8_556 4_566 ?
O3 Nd1 N3 113.1(3) 8_556 . ?
O3 Nd1 N3 113.1(3) 5 4_566 ?
O3 Nd1 N3 69.0(2) 5 . ?
O3 Nd1 N7 127.8(3) 5 8_556 ?
O3 Nd1 N7 127.8(3) 8_556 5 ?
O3 Nd1 N7 50.3(2) 8_556 8_556 ?
O3 Nd1 N7 50.3(2) 5 5 ?
O3 Nd1 C1 86.8(3) 8_556 . ?
O3 Nd1 C1 86.8(3) 5 4_566 ?
O3 Nd1 C1 95.3(2) 5 . ?
O3 Nd1 C1 95.3(2) 8_556 4_566 ?
O4 Nd1 O1 103.1(4) 4_566 . ?
O4 Nd1 O1 125.2(2) . . ?
O4 Nd1 O1 103.1(4) . 4_566 ?
O4 Nd1 O1 125.2(2) 4_566 4_566 ?
O4 Nd1 O3 115.8(3) . 5 ?
O4 Nd1 O3 62.2(3) . 8_556 ?
O4 Nd1 O3 62.2(3) 4_566 5 ?
O4 Nd1 O3 115.8(3) 4_566 8_556 ?
O4 Nd1 O4 105.9(7) . 4_566 ?
O4 Nd1 N3 78.4(4) 4_566 . ?
O4 Nd1 N3 78.3(4) . 4_566 ?
O4 Nd1 N3 174.6(3) . . ?
O4 Nd1 N3 174.6(3) 4_566 4_566 ?
O4 Nd1 N7 65.6(3) 4_566 8_556 ?
O4 Nd1 N7 77.7(4) . 8_556 ?
O4 Nd1 N7 65.6(3) . 5 ?
O4 Nd1 N7 77.7(4) 4_566 5 ?
O4 Nd1 C1 90.4(4) . 4_566 ?
O4 Nd1 C1 148.8(3) 4_566 4_566 ?
O4 Nd1 C1 90.4(4) 4_566 . ?
O4 Nd1 C1 148.8(3) . . ?
N3 Nd1 N3 97.7(5) . 4_566 ?
N3 Nd1 C1 26.3(3) . . ?
N3 Nd1 C1 87.4(4) 4_566 . ?
N3 Nd1 C1 26.3(3) 4_566 4_566 ?
N3 Nd1 C1 87.4(4) . 4_566 ?
N7 Nd1 N3 101.4(3) 5 4_566 ?
N7 Nd1 N3 119.1(3) 8_556 4_566 ?
N7 Nd1 N3 101.4(3) 8_556 . ?
N7 Nd1 N3 119.1(3) 5 . ?
N7 Nd1 N7 117.3(6) 5 8_556 ?
N7 Nd1 C1 85.5(4) 5 4_566 ?
N7 Nd1 C1 145.3(3) 8_556 4_566 ?
N7 Nd1 C1 145.3(3) 5 . ?
N7 Nd1 C1 85.5(4) 8_556 . ?
C1 Nd1 C1 88.6(5) . 4_566 ?
O2 Nd2 O2 97.8(7) . 3_656 ?
O2 Nd2 O3 62.9(2) 3_656 5 ?
O2 Nd2 O3 62.9(2) . 7_556 ?
O2 Nd2 O3 119.1(2) 3_656 7_556 ?
O2 Nd2 O3 119.1(2) . 5 ?
O2 Nd2 N4 75.9(5) 3_656 . ?
O2 Nd2 N4 50.8(3) 3_656 3_656 ?
O2 Nd2 N4 50.8(3) . . ?
O2 Nd2 N4 75.9(5) . 3_656 ?
O2 Nd2 N6 79.1(4) . 7_556 ?
O2 Nd2 N6 169.4(3) 3_656 7_556 ?
O2 Nd2 N6 169.5(3) . 5 ?
O2 Nd2 N6 79.1(4) 3_656 5 ?
O2 Nd2 C3 24.1(3) 3_656 3_656 ?
O2 Nd2 C3 86.6(5) . 3_656 ?
O2 Nd2 C3 86.6(5) 3_656 . ?
O2 Nd2 C3 24.1(3) . . ?
O3 Nd2 O3 177.4(3) 7_556 5 ?
O3 Nd2 N4 68.3(3) 5 . ?
O3 Nd2 N4 113.6(3) 7_556 . ?
O3 Nd2 N4 113.6(3) 5 3_656 ?
O3 Nd2 N4 68.3(3) 7_556 3_656 ?
O3 Nd2 N6 50.5(3) 7_556 7_556 ?
O3 Nd2 N6 127.5(3) 5 7_556 ?
O3 Nd2 N6 50.5(3) 5 5 ?
O3 Nd2 N6 127.5(3) 7_556 5 ?
O3 Nd2 C3 87.0(3) 7_556 . ?
O3 Nd2 C3 95.0(2) 5 . ?
O3 Nd2 C3 95.0(2) 7_556 3_656 ?
O3 Nd2 C3 87.0(3) 5 3_656 ?
O5 Nd2 O2 98.3(5) 3_656 3_656 ?
O5 Nd2 O2 125.6(3) 3_656 . ?
O5 Nd2 O2 98.3(5) . . ?
O5 Nd2 O2 125.6(3) . 3_656 ?
O5 Nd2 O3 63.8(3) . 5 ?
O5 Nd2 O3 114.6(3) 3_656 5 ?
O5 Nd2 O3 114.6(3) . 7_556 ?
O5 Nd2 O3 63.8(3) 3_656 7_556 ?
O5 Nd2 O5 113.0(6) 3_656 . ?
O5 Nd2 N4 171.7(5) . 3_656 ?
O5 Nd2 N4 75.3(4) 3_656 3_656 ?
O5 Nd2 N4 171.7(5) 3_656 . ?
O5 Nd2 N4 75.3(4) . . ?
O5 Nd2 N6 75.9(4) . 5 ?
O5 Nd2 N6 75.9(4) 3_656 7_556 ?
O5 Nd2 N6 65.0(3) . 7_556 ?
O5 Nd2 N6 65.0(3) 3_656 5 ?
O5 Nd2 C3 87.6(5) 3_656 3_656 ?
O5 Nd2 C3 87.6(5) . . ?
O5 Nd2 C3 149.0(3) 3_656 . ?
O5 Nd2 C3 149.0(3) . 3_656 ?
N4 Nd2 N4 96.4(7) 3_656 . ?
N4 Nd2 C3 84.7(5) 3_656 . ?
N4 Nd2 C3 26.7(3) 3_656 3_656 ?
N4 Nd2 C3 26.7(3) . . ?
N4 Nd2 C3 84.7(5) . 3_656 ?
N6 Nd2 N4 108.9(5) 5 3_656 ?
N6 Nd2 N4 118.7(3) 7_556 3_656 ?
N6 Nd2 N4 118.7(3) 5 . ?
N6 Nd2 N4 108.9(5) 7_556 . ?
N6 Nd2 N6 105.8(6) 5 7_556 ?
N6 Nd2 C3 145.4(3) 7_556 3_656 ?
N6 Nd2 C3 93.9(4) 5 3_656 ?
N6 Nd2 C3 145.4(3) 5 . ?
N6 Nd2 C3 93.9(4) 7_556 . ?
C3 Nd2 C3 84.7(7) . 3_656 ?
C1 O1 Nd1 103.2(7) . . ?
C3 O2 Nd2 101.4(7) . . ?
Nd1 O3 Nd2 160.6(3) 5_445 5_445 ?
C5 O3 Nd1 99.9(5) . 5_445 ?
C5 O3 Nd2 99.3(5) . 5_445 ?
Nd1 O4 H4A 126.1 . . ?
Nd1 O4 H4B 127.1 . . ?
H4A O4 H4B 104.5 . . ?
Nd2 O5 H5A 142.6 . . ?
Nd2 O5 H5B 110.5 . . ?
H5A O5 H5B 104.5 . . ?
C2 N1 C4 120.3(9) . . ?
C6 N1 C2 119.7(9) . . ?
C6 N1 C4 119.9(8) . . ?
C6 N2 C1 117.1(16) . . ?
C1 N3 Nd1 91.4(6) . . ?
C2 N3 Nd1 148.2(8) . . ?
C2 N3 C1 120.2(10) . . ?
C2 N4 Nd2 149.7(8) . . ?
C2 N4 C3 119.6(11) . . ?
C3 N4 Nd2 90.7(7) . . ?
C4 N5 C3 116.7(16) . . ?
C4 N6 Nd2 148.9(9) . 5_445 ?
C4 N6 C5 118.5(11) . . ?
C5 N6 Nd2 92.6(7) . 5_445 ?
C5 N7 Nd1 92.7(6) . 5_445 ?
C6 N7 Nd1 149.7(8) . 5_445 ?
C6 N7 C5 117.4(9) . . ?
O1 C1 Nd1 53.3(5) . . ?
O1 C1 N2 120.0(13) . . ?
O1 C1 N3 115.3(9) . . ?
N2 C1 Nd1 171.3(11) . . ?
N3 C1 Nd1 62.2(6) . . ?
N3 C1 N2 124.6(13) . . ?
N3 C2 N1 118.1(10) . . ?
N3 C2 N4 123.9(9) . . ?
N4 C2 N1 118.0(10) . . ?
O2 C3 Nd2 54.5(6) . . ?
O2 C3 N4 117.0(11) . . ?
O2 C3 N5 118.1(13) . . ?
N4 C3 Nd2 62.5(7) . . ?
N4 C3 N5 124.8(13) . . ?
N5 C3 Nd2 171.3(12) . . ?
N5 C4 N1 120.5(11) . . ?
N6 C4 N1 118.8(10) . . ?
N6 C4 N5 120.7(12) . . ?
Nd1 C5 Nd2 112.8(3) 5_445 5_445 ?
O3 C5 Nd1 56.2(5) . 5_445 ?
O3 C5 Nd2 56.7(4) . 5_445 ?
O3 C5 N6 117.6(9) . . ?
O3 C5 N7 117.2(9) . . ?
N6 C5 Nd1 173.7(7) . 5_445 ?
N6 C5 Nd2 60.9(6) . 5_445 ?
N7 C5 Nd1 61.0(5) . 5_445 ?
N7 C5 Nd2 173.7(7) . 5_445 ?
N7 C5 N6 125.2(9) . . ?
N2 C6 N1 120.2(10) . . ?
N7 C6 N1 119.9(9) . . ?
N7 C6 N2 119.8(11) . . ?
H6AA O6A H6AB 104.6 . . ?
H6B O6B H6B 107.8 . 3_556 ?
H7AA O7A H7AB 109.4 . . ?
H7BA O7B H7BB 104.5 . . ?
H7CA O7C H7CB 114.3 . . ?
H8A O8A H8A 106.9 . 4_566 ?
H8BA O8B H8BB 109.5 . . ?
H8CA O8C H8CB 104.5 . . ?

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
_geom_hbond_publ_flag
O4 H4A O2 0.87 1.95 2.805(13) 167.6 2_664 yes
O4 H4B N2 0.87 1.98 2.791(17) 153.6 5 yes
O5 H5A O1 0.87 2.04 2.793(13) 144.7 4_566 yes
O5 H5B N5 0.87 1.90 2.761(17) 171.8 7_556 yes
O5 H5B N6 0.87 2.32 2.766(11) 111.8 7_556 yes
O6A H6AA O7C 0.87 1.75 2.49(14) 141.1 . yes
O6A H6AB O2 0.87 2.62 3.18(7) 122.7 . yes
O6A H6AB N5 0.87 2.66 3.52(7) 169.7 . yes
O6B H6B N5 0.87 2.48 3.33(3) 164.0 . yes
O7A H7AA N1 0.87 2.45 3.24(7) 150.4 5_455 yes
O7B H7BA O5 0.87 2.23 3.10(9) 173.9 . yes
O7B H7BB O8A 0.87 2.31 3.16(11) 167.4 . yes
O7C H7CA O6A 0.83 2.27 3.10(12) 177.6 3_556 yes
O7C H7CB N5 0.87 2.38 3.25(10) 177.7 7_556 yes
O8A H8A O7A 0.86 2.52 3.36(9) 164.3 4_566 yes
O8A H8A O7B 0.86 2.54 3.16(11) 129.9 4_566 yes
O8B H8BA O7C 0.87 2.61 3.47(12) 168.9 . yes
O8B H8BB N1 0.87 2.40 3.27(10) 171.8 . yes
O8C H8CA O7A 0.87 2.53 3.38(10) 165.1 . yes
O8C H8CA O7B 0.87 2.54 3.37(13) 158.8 . yes
O8C H8CB O8A 0.87 1.73 2.25(11) 116.1 . yes

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
Nd1 O1 C1 N2 -173.3(11) . . . . ?
Nd1 O1 C1 N3 5.2(14) . . . . ?
Nd1 O3 C5 Nd2 177.5(4) 5_445 . . 5_445 ?
Nd1 O3 C5 N6 179.0(10) 5_445 . . . ?
Nd1 O3 C5 N7 -0.9(11) 5_445 . . . ?
Nd1 N3 C1 O1 -4.7(12) . . . . ?
Nd1 N3 C1 N2 173.7(13) . . . . ?
Nd1 N3 C2 N1 -171.6(13) . . . . ?
Nd1 N3 C2 N4 9(3) . . . . ?
Nd1 N7 C5 O3 0.9(11) 5_445 . . . ?
Nd1 N7 C5 N6 -179.0(12) 5_445 . . . ?
Nd1 N7 C6 N1 177.2(13) 5_445 . . . ?
Nd1 N7 C6 N2 -5(3) 5_445 . . . ?
Nd2 O2 C3 N4 -2(2) . . . . ?
Nd2 O2 C3 N5 174.7(14) . . . . ?
Nd2 O3 C5 Nd1 -177.5(4) 5_445 . . 5_445 ?
Nd2 O3 C5 N6 1.5(12) 5_445 . . . ?
Nd2 O3 C5 N7 -178.4(9) 5_445 . . . ?
Nd2 N4 C2 N1 176.5(18) . . . . ?
Nd2 N4 C2 N3 -4(4) . . . . ?
Nd2 N4 C3 O2 2.2(18) . . . . ?
Nd2 N4 C3 N5 -174.7(18) . . . . ?
Nd2 N6 C4 N1 -176.4(15) 5_445 . . . ?
Nd2 N6 C4 N5 4(4) 5_445 . . . ?
Nd2 N6 C5 O3 -1.4(11) 5_445 . . . ?
Nd2 N6 C5 N7 178.5(11) 5_445 . . . ?
C1 N2 C6 N1 0(2) . . . . ?
C1 N2 C6 N7 -177.3(14) . . . . ?
C1 N3 C2 N1 2(2) . . . . ?
C1 N3 C2 N4 -177.8(15) . . . . ?
C2 N1 C4 N5 0(2) . . . . ?
C2 N1 C4 N6 -179.6(15) . . . . ?
C2 N1 C6 N2 -1(2) . . . . ?
C2 N1 C6 N7 176.4(14) . . . . ?
C2 N3 C1 Nd1 -176.5(15) . . . . ?
C2 N3 C1 O1 178.8(14) . . . . ?
C2 N3 C1 N2 -3(2) . . . . ?
C2 N4 C3 Nd2 178.6(19) . . . . ?
C2 N4 C3 O2 -179.2(17) . . . . ?
C2 N4 C3 N5 4(3) . . . . ?
C3 N4 C2 N1 -1(2) . . . . ?
C3 N4 C2 N3 178.7(17) . . . . ?
C3 N5 C4 N1 3(2) . . . . ?
C3 N5 C4 N6 -177.6(17) . . . . ?
C4 N1 C2 N3 179.5(13) . . . . ?
C4 N1 C2 N4 -1(2) . . . . ?
C4 N1 C6 N2 179.5(14) . . . . ?
C4 N1 C6 N7 -3(2) . . . . ?
C4 N5 C3 O2 178.0(16) . . . . ?
C4 N5 C3 N4 -5(3) . . . . ?
C4 N6 C5 Nd2 -179.1(18) . . . 5_445 ?
C4 N6 C5 O3 179.5(14) . . . . ?
C4 N6 C5 N7 -1(2) . . . . ?
C5 N6 C4 N1 2(2) . . . . ?
C5 N6 C4 N5 -177.3(14) . . . . ?
C5 N7 C6 N1 4(2) . . . . ?
C5 N7 C6 N2 -178.3(12) . . . . ?
C6 N1 C2 N3 0(2) . . . . ?
C6 N1 C2 N4 179.6(14) . . . . ?
C6 N1 C4 N5 179.1(15) . . . . ?
C6 N1 C4 N6 0(2) . . . . ?
C6 N2 C1 O1 -179.9(13) . . . . ?
C6 N2 C1 N3 2(2) . . . . ?
C6 N7 C5 Nd1 176.4(15) . . . 5_445 ?
C6 N7 C5 O3 177.3(12) . . . . ?
C6 N7 C5 N6 -3(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.507(14)
2 0.493(14)

####################################################################### 
# 
# 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_ada2452
_database_code_depnum_ccdc_archive 'CCDC 2104592'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2021-12-19 deposited with the CCDC.	2022-12-15 downloaded from the CCDC.
;


# start Validation Reply Form
_vrf_PLAT430_ada2452             
;
PROBLEM: Short Inter D...A Contact  O1       ..O2       .       2.65 Ang.  
RESPONSE: 

This test alerts for possibly missed Hydrogen bonds as indicated by short  
(i.e. shorter than sum of the van der Waals radii - 0.2 Angstrom)  
Donor - Acceptor atom distances. However no hydrogen are present or expected 
on these C=O oxygen atoms from the cyamelurate molecule. This corresponds to a
short C=O .. O=C contact from the geometry of the coordination to the Ln 
centre as observed in other similar published derivatives.
;
# end Validation Reply Form




_audit_creation_date             2020-02-07
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 N7 Nd O5'
_chemical_formula_sum            'C6 H4 N7 Nd O5'
_chemical_formula_weight         398.40
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nd Nd -3.1807 10.9079 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           91
_space_group_name_H-M_alt        'P 41 2 2'
_space_group_name_Hall           'P 4w 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'
'-x, y, -z'
'x, -y, -z+1/2'
'y, x, -z+3/4'
'-y, -x, -z+1/4'

_cell_length_a                   8.6409(2)
_cell_length_b                   8.6409(2)
_cell_length_c                   20.1002(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1500.78(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9022
_cell_measurement_temperature    100
_cell_measurement_theta_max      69.877
_cell_measurement_theta_min      5.119
_shelx_estimated_absorpt_T_max   0.349
_shelx_estimated_absorpt_T_min   0.298
_exptl_absorpt_coefficient_mu    26.672
_exptl_absorpt_correction_T_max  0.1348
_exptl_absorpt_correction_T_min  0.0357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0780 before and 0.0460 after correction.
The Ratio of minimum to maximum transmission is 0.2648.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       octahedron
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0082
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            41941
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.985
_diffrn_reflns_theta_min         5.118
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Microfocus Source'
_diffrn_source_current           0.65
_diffrn_source_power             0.02912
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_diffrn_source_voltage           44.8
_reflns_Friedel_coverage         0.588
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1424
_reflns_number_total             1434
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
SAINT (2013) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2013) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         1.985
_refine_diff_density_min         -1.490
_refine_diff_density_rms         0.158
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.20(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     90
_refine_ls_number_reflns         1434
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.062
_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)+(0.0948P)²+6.0132P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1321
_refine_special_details          
'Refined as a 2-component inversion twin.,Twin,SQUEEZE'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.80(2)
 0.20(2)
2. Fixed Uiso
 At 1.5 times of:
  All O(H,H) groups
3.a Riding coordinates:
 O3(H3A,H3B)
;
_atom_sites_solution_hydrogens   difmap
_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
Nd1 Nd 0.45942(6) 0.45942(6) 0.375000 0.0343(3) Uani 1 2 d S T P . .
O1 O 0.4096(12) 0.500000 0.250000 0.0329(19) Uani 1 2 d S T P . .
O2 O -0.2671(10) 0.5469(14) 0.0837(3) 0.055(2) Uani 1 1 d . . . . .
N1 N 0.1942(11) 0.4768(14) 0.3092(4) 0.039(2) Uani 1 1 d . . . . .
N2 N -0.0336(10) 0.4646(13) 0.3671(4) 0.047(2) Uani 1 1 d . . . . .
N3 N -0.0384(15) 0.500000 0.250000 0.045(3) Uani 1 2 d S T P . .
N4 N -0.2737(12) 0.5140(17) 0.1930(5) 0.049(3) Uani 1 1 d . . . . .
C1 C 0.2660(18) 0.500000 0.250000 0.032(3) Uani 1 2 d S T P . .
C2 C 0.0432(12) 0.4795(15) 0.3096(5) 0.039(2) Uani 1 1 d . . . . .
C3 C -0.2009(19) 0.500000 0.250000 0.048(4) Uani 1 2 d S T P . .
C4 C -0.1898(13) 0.5311(17) 0.1363(5) 0.047(3) Uani 1 1 d . . . . .
O3 O 0.2239(10) 0.466(2) 0.4464(4) 0.076(4) Uani 1 1 d . . . . .
H3A H 0.147796 0.516700 0.435475 0.114 Uiso 1 1 d R U . . .
H3B H 0.239276 0.452820 0.486665 0.114 Uiso 1 1 d 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
Nd1 O1 2.5732(17) 3_655 ?
Nd1 O1 2.5732(17) . ?
Nd1 O2 2.505(8) 6_665 ?
Nd1 O2 2.505(8) 3_665 ?
Nd1 N1 2.650(9) . ?
Nd1 N1 2.650(9) 7 ?
Nd1 N4 2.690(10) 6_665 ?
Nd1 N4 2.690(10) 3_665 ?
Nd1 C1 3.038(8) 3_655 ?
Nd1 C1 3.038(8) . ?
Nd1 O3 2.491(9) 7 ?
Nd1 O3 2.491(9) . ?
O1 C1 1.240(19) . ?
O2 C4 1.257(13) . ?
N1 C1 1.357(11) . ?
N1 C2 1.305(15) . ?
N2 C2 1.340(13) . ?
N2 C4 1.352(15) 6_565 ?
N3 C2 1.401(12) 6_565 ?
N3 C2 1.401(12) . ?
N3 C3 1.40(2) . ?
N4 C3 1.314(12) . ?
N4 C4 1.359(14) . ?
O3 H3A 0.8199 . ?
O3 H3B 0.8276 . ?

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 Nd1 O1 177.5(3) 3_655 . ?
O1 Nd1 N1 127.92(18) . 7 ?
O1 Nd1 N1 50.2(3) . . ?
O1 Nd1 N1 50.2(3) 3_655 7 ?
O1 Nd1 N1 127.92(19) 3_655 . ?
O1 Nd1 N4 68.7(3) 3_655 3_665 ?
O1 Nd1 N4 68.7(3) . 6_665 ?
O1 Nd1 N4 113.2(2) 3_655 6_665 ?
O1 Nd1 N4 113.2(2) . 3_665 ?
O1 Nd1 C1 23.7(3) 3_655 3_655 ?
O1 Nd1 C1 23.7(3) . . ?
O1 Nd1 C1 154.4(2) 3_655 . ?
O1 Nd1 C1 154.4(2) . 3_655 ?
O2 Nd1 O1 62.88(17) 6_665 3_655 ?
O2 Nd1 O1 62.88(17) 3_665 . ?
O2 Nd1 O1 119.0(3) 3_665 3_655 ?
O2 Nd1 O1 119.0(3) 6_665 . ?
O2 Nd1 O2 98.7(5) 6_665 3_665 ?
O2 Nd1 N1 76.3(3) 3_665 . ?
O2 Nd1 N1 169.2(2) 6_665 . ?
O2 Nd1 N1 169.2(2) 3_665 7 ?
O2 Nd1 N1 76.3(3) 6_665 7 ?
O2 Nd1 N4 76.7(4) 3_665 6_665 ?
O2 Nd1 N4 50.3(3) 6_665 6_665 ?
O2 Nd1 N4 76.7(4) 6_665 3_665 ?
O2 Nd1 N4 50.3(3) 3_665 3_665 ?
O2 Nd1 C1 66.7(2) 3_665 . ?
O2 Nd1 C1 66.7(2) 6_665 3_655 ?
O2 Nd1 C1 142.7(3) 3_665 3_655 ?
O2 Nd1 C1 142.7(3) 6_665 . ?
N1 Nd1 N1 110.3(5) 7 . ?
N1 Nd1 N4 118.9(3) . 6_665 ?
N1 Nd1 N4 106.2(4) . 3_665 ?
N1 Nd1 N4 106.2(4) 7 6_665 ?
N1 Nd1 N4 118.9(3) 7 3_665 ?
N1 Nd1 C1 122.9(2) 7 . ?
N1 Nd1 C1 122.9(2) . 3_655 ?
N1 Nd1 C1 26.5(3) 7 3_655 ?
N1 Nd1 C1 26.5(3) . . ?
N4 Nd1 N4 96.4(6) 3_665 6_665 ?
N4 Nd1 C1 92.4(3) 3_665 3_655 ?
N4 Nd1 C1 111.6(3) 6_665 3_655 ?
N4 Nd1 C1 92.4(3) 6_665 . ?
N4 Nd1 C1 111.6(3) 3_665 . ?
C1 Nd1 C1 144.2(3) . 3_655 ?
O3 Nd1 O1 115.0(3) . . ?
O3 Nd1 O1 63.42(19) 7 . ?
O3 Nd1 O1 115.0(3) 7 3_655 ?
O3 Nd1 O1 63.42(19) . 3_655 ?
O3 Nd1 O2 125.5(2) . 6_665 ?
O3 Nd1 O2 98.7(5) 7 6_665 ?
O3 Nd1 O2 125.5(2) 7 3_665 ?
O3 Nd1 O2 98.7(5) . 3_665 ?
O3 Nd1 N1 65.2(3) . . ?
O3 Nd1 N1 77.2(4) 7 . ?
O3 Nd1 N1 77.2(4) . 7 ?
O3 Nd1 N1 65.1(3) 7 7 ?
O3 Nd1 N4 76.0(4) 7 6_665 ?
O3 Nd1 N4 172.3(5) 7 3_665 ?
O3 Nd1 N4 76.0(4) . 3_665 ?
O3 Nd1 N4 172.3(5) . 6_665 ?
O3 Nd1 C1 68.3(3) 7 . ?
O3 Nd1 C1 91.4(3) . . ?
O3 Nd1 C1 68.3(3) . 3_655 ?
O3 Nd1 C1 91.4(3) 7 3_655 ?
O3 Nd1 O3 111.7(8) 7 . ?
Nd1 O1 Nd1 160.7(4) . 4_564 ?
C1 O1 Nd1 99.6(2) . 4_564 ?
C1 O1 Nd1 99.6(2) . . ?
C4 O2 Nd1 102.7(6) . 4_464 ?
C1 N1 Nd1 92.9(7) . . ?
C2 N1 Nd1 149.6(7) . . ?
C2 N1 C1 117.4(10) . . ?
C2 N2 C4 116.7(9) . 6_565 ?
C2 N3 C2 119.6(13) . 6_565 ?
C2 N3 C3 120.2(6) 6_565 . ?
C2 N3 C3 120.2(6) . . ?
C3 N4 Nd1 149.5(9) . 4_464 ?
C3 N4 C4 119.1(11) . . ?
C4 N4 Nd1 91.3(6) . 4_464 ?
Nd1 C1 Nd1 113.3(5) 4_564 . ?
O1 C1 Nd1 56.6(2) . . ?
O1 C1 Nd1 56.6(2) . 4_564 ?
O1 C1 N1 117.2(7) . 6_565 ?
O1 C1 N1 117.2(7) . . ?
N1 C1 Nd1 60.6(5) . . ?
N1 C1 Nd1 60.6(5) 6_565 4_564 ?
N1 C1 Nd1 173.7(9) . 4_564 ?
N1 C1 Nd1 173.7(9) 6_565 . ?
N1 C1 N1 125.5(14) . 6_565 ?
N1 C2 N2 119.9(10) . . ?
N1 C2 N3 120.0(10) . . ?
N2 C2 N3 120.1(10) . . ?
N4 C3 N3 118.6(8) 6_565 . ?
N4 C3 N3 118.6(8) . . ?
N4 C3 N4 122.7(16) . 6_565 ?
O2 C4 Nd1 53.5(6) . 4_464 ?
O2 C4 N2 119.0(10) . 6_565 ?
O2 C4 N4 115.7(10) . . ?
N2 C4 Nd1 172.2(8) 6_565 4_464 ?
N2 C4 N4 125.3(10) 6_565 . ?
N4 C4 Nd1 62.2(6) . 4_464 ?
Nd1 O3 H3A 120.8 . . ?
Nd1 O3 H3B 115.4 . . ?
H3A O3 H3B 117.7 . . ?

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
_geom_hbond_publ_flag
O3 H3A N2 0.82 2.13 2.737(13) 130.5 . yes
O3 H3B O2 0.83 1.96 2.786(11) 171.7 2_565 yes

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
Nd1 O1 C1 Nd1 180.000(2) 4_564 . . . ?
Nd1 O1 C1 Nd1 180.000(1) . . . 4_564 ?
Nd1 O1 C1 N1 178.4(6) . . . 6_565 ?
Nd1 O1 C1 N1 178.4(6) 4_564 . . . ?
Nd1 O1 C1 N1 -1.6(6) 4_564 . . 6_565 ?
Nd1 O1 C1 N1 -1.6(6) . . . . ?
Nd1 O2 C4 N2 -177.4(11) 4_464 . . 6_565 ?
Nd1 O2 C4 N4 1.2(14) 4_464 . . . ?
Nd1 N1 C1 O1 1.6(5) . . . . ?
Nd1 N1 C1 N1 -178.4(5) . . . 6_565 ?
Nd1 N1 C2 N2 -2(3) . . . . ?
Nd1 N1 C2 N3 176.8(11) . . . . ?
Nd1 N4 C3 N3 -176.4(13) 4_464 . . . ?
Nd1 N4 C3 N4 3.6(13) 4_464 . . 6_565 ?
Nd1 N4 C4 O2 -1.1(13) 4_464 . . . ?
Nd1 N4 C4 N2 177.4(14) 4_464 . . 6_565 ?
C1 N1 C2 N2 -176.9(10) . . . . ?
C1 N1 C2 N3 2.4(18) . . . . ?
C2 N1 C1 Nd1 177.2(14) . . . . ?
C2 N1 C1 O1 178.8(9) . . . . ?
C2 N1 C1 N1 -1.2(9) . . . 6_565 ?
C2 N3 C2 N1 -1.3(10) 6_565 . . . ?
C2 N3 C2 N2 178.0(14) 6_565 . . . ?
C2 N3 C3 N4 2.4(9) . . . 6_565 ?
C2 N3 C3 N4 -177.6(9) . . . . ?
C2 N3 C3 N4 2.4(9) 6_565 . . . ?
C2 N3 C3 N4 -177.6(9) 6_565 . . 6_565 ?
C3 N3 C2 N1 178.7(10) . . . . ?
C3 N3 C2 N2 -2.0(14) . . . . ?
C3 N4 C4 Nd1 -177.5(14) . . . 4_464 ?
C3 N4 C4 O2 -178.7(13) . . . . ?
C3 N4 C4 N2 0(2) . . . 6_565 ?
C4 N2 C2 N1 179.8(13) 6_565 . . . ?
C4 N2 C2 N3 0.6(18) 6_565 . . . ?
C4 N4 C3 N3 -1.3(15) . . . . ?
C4 N4 C3 N4 178.7(15) . . . 6_565 ?

_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 0.000 -0.290 646.3 125.7 '3.2 C3H7NO'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.80(2)
2 0.20(2)

