# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_er-cy
_database_code_depnum_ccdc_archive 'CCDC 2178356'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2022-06-10 deposited with the CCDC.	2022-09-01 downloaded from the CCDC.
;
_audit_creation_date             2022-03-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H8 Er N7 O7, H2 O'
_chemical_formula_sum            'C6 H10 Er N7 O8'
_chemical_formula_weight         475.47
_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'
Er Er -9.4367 3.9380 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   5.69360(10)
_cell_length_b                   12.0266(3)
_cell_length_c                   17.6197(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.8670(10)
_cell_angle_gamma                90
_cell_volume                     1206.36(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.708
_cell_measurement_theta_min      2.508
_shelx_estimated_absorpt_T_max   0.773
_shelx_estimated_absorpt_T_min   0.236
_exptl_absorpt_coefficient_mu    13.558
_exptl_absorpt_correction_T_max  0.0565
_exptl_absorpt_correction_T_min  0.0027
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1000 before and 0.0268 after correction. The Ratio of minimum to maximum transmission is 0.0478. 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    2.618
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             908
_exptl_crystal_recrystallization_method 'crystallized form EtOH'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_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  0.0190
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14564
_diffrn_reflns_point_group_measured_fraction_full 0.907
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.701
_diffrn_reflns_theta_min         5.021
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           0.65
_diffrn_source_power             0.029119999999999997
_diffrn_source_voltage           44.8
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    0.817
_reflns_Friedel_fraction_max     0.815
_reflns_number_gt                2123
_reflns_number_total             2123
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.543
_refine_diff_density_min         -1.192
_refine_diff_density_rms         0.168
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.080(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2123
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0244
_refine_ls_restrained_S_all      1.123
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0477P)²+0.4017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0592
_refine_ls_wR_factor_ref         0.0592
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.920(15)
 0.080(15)
2. Fixed Uiso
 At 1.5 times of:
  All O(H,H,H,H,H,H,H,H,H,H) groups
3. Restrained distances
 O4-H4A \\sim O4-H4B \\sim O5-H5A \\sim O5-H5B \\sim O7-H7A \\sim O7-H7B \\sim
O8-H8A \\sim O8-H8B
 with sigma of 0.02
 H4A-H4B \\sim H5A-H5B \\sim H7A-H7B \\sim H8A-H8B
 with sigma of 0.02
4.a Rotating group:
 C6(O4,O5,O6,O7,O8,H5A,H5B), O8(H4A,H4B), O8(H8A,H8B), O8(H7A,H7B), O8(H6A,H6B)
;
_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
Er1 Er 0.37742(6) 0.64013(2) 0.30595(4) 0.03626(13) Uani 1 1 d . . . . .
O1 O 0.7022(7) 0.6836(3) 0.3969(2) 0.0366(8) Uani 1 1 d . . . . .
O2 O -0.1636(9) 0.3409(4) 0.5072(3) 0.0406(9) Uani 1 1 d . . . . .
O3 O 0.6744(8) 0.4843(3) 0.7632(2) 0.0399(9) Uani 1 1 d . . . . .
N1 N 0.4442(10) 0.5556(4) 0.4294(3) 0.0373(10) Uani 1 1 d . . . . .
N2 N 0.1418(10) 0.4419(4) 0.4644(3) 0.0396(11) Uani 1 1 d . . . . .
N3 N 0.7310(12) 0.6203(5) 0.5208(4) 0.0398(13) Uani 1 1 d . . . . .
N4 N 0.4282(8) 0.4963(4) 0.5543(3) 0.0373(10) Uani 1 1 d . . . . .
N5 N 0.1200(13) 0.3792(5) 0.5937(3) 0.0397(13) Uani 1 1 d . . . . .
N6 N 0.7203(10) 0.5561(4) 0.6436(3) 0.0395(10) Uani 1 1 d . . . . .
N7 N 0.4064(10) 0.4340(4) 0.6797(3) 0.0375(10) Uani 1 1 d . . . . .
C1 C 0.6319(11) 0.6203(5) 0.4503(3) 0.0386(12) Uani 1 1 d . . . . .
C2 C 0.3372(11) 0.4979(4) 0.4813(3) 0.0382(11) Uani 1 1 d . . . . .
C3 C 0.0292(11) 0.3865(5) 0.5210(3) 0.0376(11) Uani 1 1 d . . . . .
C4 C 0.6297(11) 0.5596(4) 0.5730(3) 0.0377(11) Uani 1 1 d . . . . .
C5 C 0.3139(11) 0.4351(4) 0.6095(3) 0.0371(10) Uani 1 1 d . . . . .
C6 C 0.6045(3) 0.49346(15) 0.69407(10) 0.0367(10) Uani 1 1 d . . . . .
O4 O 0.1053(4) 0.49340(16) 0.31632(11) 0.0385(8) Uani 1 1 d DR . . . .
O5 O 0.0666(4) 0.70974(14) 0.23484(10) 0.0402(9) Uani 1 1 d DR . . . .
O6 O 0.5980(4) 0.7816(2) 0.25069(10) 0.0383(9) Uani 1 1 d R . . . .
O7 O 0.1599(4) 0.75593(14) 0.38231(10) 0.0399(9) Uani 1 1 d DR . . . .
O8 O -0.3573(4) 0.19580(17) 0.60507(10) 0.0433(9) Uani 1 1 d DR . . . .
H5A H -0.058647 0.734904 0.249880 0.065 Uiso 1 1 d DR U . . .
H5B H 0.060143 0.682465 0.191531 0.065 Uiso 1 1 d DR U . . .
H4A H 0.096966 0.469913 0.360709 0.065 Uiso 1 1 d DR U . . .
H4B H -0.025567 0.516652 0.300279 0.065 Uiso 1 1 d DR U . . .
H8A H -0.299074 0.244262 0.577799 0.065 Uiso 1 1 d DR U . . .
H8B H -0.452404 0.155092 0.582379 0.065 Uiso 1 1 d DR U . . .
H7A H 0.025604 0.730943 0.382080 0.065 Uiso 1 1 d DR U . . .
H7B H 0.199203 0.786105 0.422761 0.065 Uiso 1 1 d DR U . . .
H6A H 0.591195 0.774839 0.201421 0.065 Uiso 1 1 d R U . . .
H6B H 0.532624 0.845407 0.259641 0.065 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
Er1 O1 2.484(4) . ?
Er1 O3 2.388(4) 2_564 ?
Er1 N1 2.425(5) . ?
Er1 N7 2.405(5) 2_564 ?
Er1 C6 2.8662(19) 2_564 ?
Er1 O4 2.3570(19) . ?
Er1 O5 2.310(2) . ?
Er1 O6 2.3363(19) . ?
Er1 O7 2.3096(19) . ?
O1 C1 1.279(8) . ?
O2 C3 1.248(8) . ?
O3 C6 1.281(5) . ?
N1 C1 1.368(8) . ?
N1 C2 1.306(8) . ?
N2 C2 1.330(8) . ?
N2 C3 1.367(8) . ?
N3 C1 1.357(9) . ?
N3 C4 1.313(9) . ?
N4 C2 1.380(8) . ?
N4 C4 1.411(8) . ?
N4 C5 1.390(7) . ?
N5 C3 1.377(9) . ?
N5 C5 1.319(10) . ?
N6 C4 1.340(8) . ?
N6 C6 1.346(5) . ?
N7 C5 1.336(8) . ?
N7 C6 1.356(6) . ?
O4 H4A 0.8336 . ?
O4 H4B 0.8410 . ?
O5 H5A 0.8221 . ?
O5 H5B 0.8309 . ?
O6 H6A 0.8722 . ?
O6 H6B 0.8682 . ?
O7 H7A 0.8215 . ?
O7 H7B 0.8276 . ?
O8 H8A 0.8278 . ?
O8 H8B 0.8284 . ?

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 Er1 C6 102.86(10) . 2_564 ?
O3 Er1 O1 79.12(14) 2_564 . ?
O3 Er1 N1 85.29(16) 2_564 . ?
O3 Er1 N7 54.35(17) 2_564 2_564 ?
O3 Er1 C6 26.26(11) 2_564 2_564 ?
N1 Er1 O1 53.46(15) . . ?
N1 Er1 C6 108.40(13) . 2_564 ?
N7 Er1 O1 127.87(17) 2_564 . ?
N7 Er1 N1 131.46(15) 2_564 . ?
N7 Er1 C6 28.10(14) 2_564 2_564 ?
O4 Er1 O1 126.24(10) . . ?
O4 Er1 O3 91.42(13) . 2_564 ?
O4 Er1 N1 73.20(12) . . ?
O4 Er1 N7 81.29(13) . 2_564 ?
O4 Er1 C6 86.41(5) . 2_564 ?
O5 Er1 O1 146.14(10) . . ?
O5 Er1 O3 126.62(11) . 2_564 ?
O5 Er1 N1 138.30(14) . . ?
O5 Er1 N7 72.27(14) . 2_564 ?
O5 Er1 C6 100.36(7) . 2_564 ?
O5 Er1 O4 79.30(6) . . ?
O5 Er1 O6 85.54(6) . . ?
O6 Er1 O1 73.50(10) . . ?
O6 Er1 O3 86.40(13) . 2_564 ?
O6 Er1 N1 126.94(13) . . ?
O6 Er1 N7 80.77(13) . 2_564 ?
O6 Er1 C6 82.57(9) . 2_564 ?
O6 Er1 O4 159.34(8) . . ?
O7 Er1 O1 84.14(11) . . ?
O7 Er1 O3 161.79(11) . 2_564 ?
O7 Er1 N1 78.96(13) . . ?
O7 Er1 N7 143.85(15) . 2_564 ?
O7 Er1 C6 171.92(8) . 2_564 ?
O7 Er1 O4 92.72(7) . . ?
O7 Er1 O5 71.59(6) . . ?
O7 Er1 O6 95.74(7) . . ?
C1 O1 Er1 96.4(4) . . ?
C6 O3 Er1 98.2(2) . 2_565 ?
C1 N1 Er1 96.6(4) . . ?
C2 N1 Er1 141.4(4) . . ?
C2 N1 C1 119.0(5) . . ?
C2 N2 C3 119.0(5) . . ?
C4 N3 C1 117.4(6) . . ?
C2 N4 C4 120.2(5) . . ?
C2 N4 C5 119.2(5) . . ?
C5 N4 C4 120.6(5) . . ?
C5 N5 C3 117.7(6) . . ?
C4 N6 C6 116.5(5) . . ?
C5 N7 Er1 145.9(4) . 2_565 ?
C5 N7 C6 118.9(5) . . ?
C6 N7 Er1 95.2(3) . 2_565 ?
O1 C1 N1 113.1(5) . . ?
O1 C1 N3 122.9(6) . . ?
N3 C1 N1 124.0(6) . . ?
N1 C2 N2 120.7(5) . . ?
N1 C2 N4 119.2(5) . . ?
N2 C2 N4 120.1(5) . . ?
O2 C3 N2 119.6(5) . . ?
O2 C3 N5 118.0(6) . . ?
N2 C3 N5 122.4(6) . . ?
N3 C4 N4 120.0(6) . . ?
N3 C4 N6 120.0(6) . . ?
N6 C4 N4 120.0(5) . . ?
N5 C5 N4 121.4(5) . . ?
N5 C5 N7 120.5(6) . . ?
N7 C5 N4 118.1(5) . . ?
O3 C6 Er1 55.6(2) . 2_565 ?
O3 C6 N6 121.9(3) . . ?
O3 C6 N7 112.2(3) . . ?
N6 C6 Er1 177.3(3) . 2_565 ?
N6 C6 N7 125.9(3) . . ?
N7 C6 Er1 56.7(2) . 2_565 ?
Er1 O4 H4A 111.9 . . ?
Er1 O4 H4B 107.8 . . ?
H4A O4 H4B 111.4 . . ?
Er1 O5 H5A 128.3 . . ?
Er1 O5 H5B 112.2 . . ?
H5A O5 H5B 114.5 . . ?
Er1 O6 H6A 109.3 . . ?
Er1 O6 H6B 109.5 . . ?
H6A O6 H6B 104.5 . . ?
Er1 O7 H7A 106.5 . . ?
Er1 O7 H7B 128.7 . . ?
H7A O7 H7B 113.8 . . ?
H8A O8 H8B 113.6 . . ?

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
O5 H5A O6 0.82 2.03 2.822 160.4 1_455 yes
O5 H5B N5 0.83 1.91 2.728(7) 167.2 2_564 yes
O4 H4A N2 0.83 1.87 2.687(5) 165.5 . yes
O4 H4B O3 0.84 1.82 2.626(5) 160.2 2_464 yes
O8 H8A O2 0.83 1.88 2.700(5) 173.2 . yes
O8 H8B N3 0.83 2.13 2.901(7) 154.6 3_345 yes
O8 H8B N6 0.83 2.47 3.019(6) 124.4 3_345 yes
O7 H7A O1 0.82 1.95 2.763(5) 170.9 1_455 yes
O7 H7B O2 0.83 1.80 2.613(5) 169.5 3 yes
O6 H6A O8 0.87 1.76 2.596 159.1 2_664 yes
O6 H6B O4 0.87 2.08 2.797 139.5 3 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
Er1 O1 C1 N1 6.7(5) . . . . ?
Er1 O1 C1 N3 -171.6(6) . . . . ?
Er1 O3 C6 N6 -178.9(3) 2_565 . . . ?
Er1 O3 C6 N7 1.1(3) 2_565 . . . ?
Er1 N1 C1 O1 -6.9(6) . . . . ?
Er1 N1 C1 N3 171.5(6) . . . . ?
Er1 N1 C2 N2 19.2(9) . . . . ?
Er1 N1 C2 N4 -160.3(4) . . . . ?
Er1 N7 C5 N4 -176.2(5) 2_565 . . . ?
Er1 N7 C5 N5 3.5(11) 2_565 . . . ?
Er1 N7 C6 O3 -1.1(3) 2_565 . . . ?
Er1 N7 C6 N6 178.9(3) 2_565 . . . ?
C1 N1 C2 N2 174.0(5) . . . . ?
C1 N1 C2 N4 -5.5(8) . . . . ?
C1 N3 C4 N4 1.0(9) . . . . ?
C1 N3 C4 N6 179.8(6) . . . . ?
C2 N1 C1 O1 -171.4(5) . . . . ?
C2 N1 C1 N3 7.0(10) . . . . ?
C2 N2 C3 O2 174.5(5) . . . . ?
C2 N2 C3 N5 -5.1(9) . . . . ?
C2 N4 C4 N3 0.1(8) . . . . ?
C2 N4 C4 N6 -178.7(5) . . . . ?
C2 N4 C5 N5 -0.4(8) . . . . ?
C2 N4 C5 N7 179.4(5) . . . . ?
C3 N2 C2 N1 -177.1(5) . . . . ?
C3 N2 C2 N4 2.3(8) . . . . ?
C3 N5 C5 N4 -2.2(9) . . . . ?
C3 N5 C5 N7 178.0(5) . . . . ?
C4 N3 C1 O1 173.6(6) . . . . ?
C4 N3 C1 N1 -4.6(10) . . . . ?
C4 N4 C2 N1 2.2(8) . . . . ?
C4 N4 C2 N2 -177.2(5) . . . . ?
C4 N4 C5 N5 177.2(5) . . . . ?
C4 N4 C5 N7 -3.0(8) . . . . ?
C4 N6 C6 O3 -179.8(4) . . . . ?
C4 N6 C6 N7 0.2(7) . . . . ?
C5 N4 C2 N1 179.8(5) . . . . ?
C5 N4 C2 N2 0.4(8) . . . . ?
C5 N4 C4 N3 -177.5(5) . . . . ?
C5 N4 C4 N6 3.8(8) . . . . ?
C5 N5 C3 O2 -174.6(6) . . . . ?
C5 N5 C3 N2 5.1(9) . . . . ?
C5 N7 C6 Er1 -178.4(6) . . . 2_565 ?
C5 N7 C6 O3 -179.5(4) . . . . ?
C5 N7 C6 N6 0.5(7) . . . . ?
C6 N6 C4 N3 179.0(5) . . . . ?
C6 N6 C4 N4 -2.3(8) . . . . ?
C6 N7 C5 N4 0.9(7) . . . . ?
C6 N7 C5 N5 -179.3(4) . . . . ?

_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 0.920(15)
2 0.080(15)

####################################################################### 
# 
# 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_la-cy
_database_code_depnum_ccdc_archive 'CCDC 2178357'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2022-06-10 deposited with the CCDC.	2022-09-01 downloaded from the CCDC.
;
_audit_creation_date             2022-03-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H12 La N7 O9, H2 O'
_chemical_formula_sum            'C6 H14 La N7 O10'
_chemical_formula_weight         483.15
_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 0.0140 0.0070 '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'
La La -0.4910 7.2210 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0250 '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           24
_space_group_name_H-M_alt        'I 21 21 21'
_space_group_name_Hall           'I 2b 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-x+1/2, y+1, -z+1'
'x+1, -y+1, -z+1/2'

_cell_length_a                   6.5379(2)
_cell_length_b                   10.6082(3)
_cell_length_c                   19.3914(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1344.90(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    100
_cell_measurement_theta_max      54.953
_cell_measurement_theta_min      3.968
_shelx_estimated_absorpt_T_max   0.304
_shelx_estimated_absorpt_T_min   0.230
_exptl_absorpt_coefficient_mu    17.378
_exptl_absorpt_correction_T_max  0.0766
_exptl_absorpt_correction_T_min  0.0125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1237 before and 0.0415 after correction.
The Ratio of minimum to maximum transmission is 0.1632.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light Colorless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    2.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_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 Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11309
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.927
_diffrn_reflns_theta_min         3.967
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                1269
_reflns_number_total             1271
_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) V8.37A; 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) V8.37A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         1.844
_refine_diff_density_min         -1.524
_refine_diff_density_rms         0.253
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.417(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1271
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.350
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0667P)²+0.6704P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0836
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.583(14)
 0.417(14)
2. Fixed Uiso
 At 1.5 times of:
  All O(H,H,H,H,H,H,H,H) groups
3. Restrained distances
 O4-H4A = O4-H4B = O3-H3A = O3-H3B = O5-H5A = O5-H5B = O6-H6A = O6-H6B
 0.85 with sigma of 0.002
 H4A-H4B = H3A-H3B = H5A-H5B = H6A-H6B
 1.3 with sigma of 0.002
 H4A-H3B_$3
 2.2 with sigma of 0.02
 H6A-H6A_$6
 2.2 with sigma of 0.02
4. Others
 Fixed Sof: H5A(0.5) H5B(0.5)
5.a Rotating group:
 N4(O4,O3,O2,O5,O6,H4A,H4B), O6(H6A,H6B), O6(H5A,H5B), O6(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
La1 La 1.07214(5) 0.000000 0.750000 0.0228(2) Uani 1 2 d S T P . .
O1 O 1.000000 0.250000 0.7329(3) 0.0267(13) Uani 1 2 d S T P . .
C1 C 1.000000 0.250000 0.6671(4) 0.0230(14) Uani 1 2 d S T P . .
N1 N 1.0002(10) 0.1354(4) 0.6358(3) 0.0251(10) Uani 1 1 d . . . . .
C2 C 0.9959(9) 0.1329(5) 0.5667(3) 0.0228(11) Uani 1 1 d . . . . .
N2 N 0.9901(8) 0.0280(4) 0.5326(3) 0.0263(13) Uani 1 1 d . . . . .
C3 C 0.9824(10) 0.0315(5) 0.4624(3) 0.0255(14) Uani 1 1 d . . . . .
N3 N 1.000000 0.250000 0.5313(4) 0.0223(15) Uani 1 2 d S T P . .
C4 C 1.000000 0.250000 0.4594(4) 0.0233(17) Uani 1 2 d S T P . .
N4 N 0.9926(7) 0.14220(17) 0.42540(10) 0.0263(10) Uani 1 1 d . . . . .
O4 O 1.2122(3) 0.13737(17) 0.84969(10) 0.0273(10) Uani 1 1 d DR . . . .
O3 O 0.7458(3) -0.10080(19) 0.69158(12) 0.0285(10) Uani 1 1 d DR . . . .
O2 O 0.9650(3) -0.06984(18) 0.42984(10) 0.0294(10) Uani 1 1 d R . . . .
O5 O 1.0000(3) -0.25000(17) 0.54571(10) 0.0352(17) Uani 1 2 d DR T P . .
O6 O 1.3964(3) 0.11159(19) 0.71040(14) 0.0289(10) Uani 1 1 d DR . . . .
H4A H 1.279239 0.200361 0.835102 0.043 Uiso 1 1 d DR U . . .
H4B H 1.309079 0.096591 0.868862 0.043 Uiso 1 1 d DR U . . .
H6A H 1.369898 0.183821 0.727392 0.043 Uiso 1 1 d DR U . . .
H6B H 1.427738 0.132671 0.669341 0.043 Uiso 1 1 d DR U . . .
H5A H 0.932009 -0.209740 0.575933 0.043 Uiso 0.5 1 d DR U P . .
H5B H 1.009049 -0.193170 0.514943 0.043 Uiso 0.5 1 d DR U P . .
H3A H 0.697619 -0.083131 0.650944 0.043 Uiso 1 1 d DR U . . .
H3B H 0.627879 -0.121611 0.710353 0.043 Uiso 1 1 d DR 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
La1 O1 2.7140(6) . ?
La1 O1 2.7140(6) 3_746 ?
La1 C1 3.137(4) 3_746 ?
La1 N1 2.682(5) 8_446 ?
La1 N1 2.682(5) . ?
La1 O4 2.5884(19) . ?
La1 O4 2.5884(19) 8_446 ?
La1 O3 2.642(2) . ?
La1 O3 2.642(2) 8_446 ?
La1 O6 2.547(2) . ?
La1 O6 2.547(2) 8_446 ?
O1 C1 1.277(9) . ?
C1 N1 1.359(6) 6_654 ?
C1 N1 1.359(6) . ?
N1 C2 1.339(8) . ?
C2 N2 1.295(8) . ?
C2 N3 1.420(6) . ?
N2 C3 1.363(7) . ?
C3 N4 1.378(7) . ?
C3 O2 1.252(6) . ?
N3 C4 1.393(10) . ?
C4 N4 1.321(5) . ?
C4 N4 1.321(5) 6_654 ?
O4 H4A 0.8476 . ?
O4 H4B 0.8522 . ?
O3 H3A 0.8691 . ?
O3 H3B 0.8806 . ?
O5 H5A 0.850(3) 6_644 ?
O5 H5A 0.8506 . ?
O5 H5B 0.850(3) 6_644 ?
O5 H5B 0.8503 . ?
O6 H6A 0.8519 . ?
O6 H6B 0.8520 . ?

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 La1 O1 159.984(15) 3_746 . ?
O1 La1 C1 23.82(16) 3_746 3_746 ?
O1 La1 C1 149.60(13) . 3_746 ?
N1 La1 O1 126.42(15) . 3_746 ?
N1 La1 O1 49.10(15) 8_446 3_746 ?
N1 La1 O1 126.42(15) 8_446 . ?
N1 La1 O1 49.10(15) . . ?
N1 La1 C1 25.50(15) 8_446 3_746 ?
N1 La1 C1 148.19(16) . 3_746 ?
N1 La1 N1 159.8(3) . 8_446 ?
O4 La1 O1 66.58(10) . . ?
O4 La1 O1 121.36(11) 8_446 . ?
O4 La1 O1 121.36(11) . 3_746 ?
O4 La1 O1 66.58(10) 8_446 3_746 ?
O4 La1 C1 87.71(11) 8_446 3_746 ?
O4 La1 C1 98.41(12) . 3_746 ?
O4 La1 N1 112.18(12) . . ?
O4 La1 N1 75.32(12) . 8_446 ?
O4 La1 N1 75.33(12) 8_446 . ?
O4 La1 N1 112.18(13) 8_446 8_446 ?
O4 La1 O4 138.55(10) . 8_446 ?
O4 La1 O3 74.8 8_446 . ?
O4 La1 O3 146.50(9) 8_446 8_446 ?
O4 La1 O3 146.50(9) . . ?
O4 La1 O3 74.8 . 8_446 ?
O3 La1 O1 101.70(7) 8_446 3_746 ?
O3 La1 O1 61.08(8) 8_446 . ?
O3 La1 O1 101.70(7) . . ?
O3 La1 O1 61.08(8) . 3_746 ?
O3 La1 C1 90.06(8) 8_446 3_746 ?
O3 La1 C1 75.89(9) . 3_746 ?
O3 La1 N1 73.79(14) 8_446 8_446 ?
O3 La1 N1 89.75(14) 8_446 . ?
O3 La1 N1 89.75(14) . 8_446 ?
O3 La1 N1 73.79(14) . . ?
O3 La1 O3 72.26(9) 8_446 . ?
O6 La1 O1 69.74(5) 8_446 3_746 ?
O6 La1 O1 129.47(5) 8_446 . ?
O6 La1 O1 69.74(5) . . ?
O6 La1 O1 129.47(5) . 3_746 ?
O6 La1 C1 132.27(5) . 3_746 ?
O6 La1 C1 65.02(5) 8_446 3_746 ?
O6 La1 N1 69.40(16) 8_446 8_446 ?
O6 La1 N1 130.10(14) . 8_446 ?
O6 La1 N1 69.39(16) . . ?
O6 La1 N1 130.09(14) 8_446 . ?
O6 La1 O4 70.7 . . ?
O6 La1 O4 70.7 8_446 8_446 ?
O6 La1 O4 75.04(8) . 8_446 ?
O6 La1 O4 75.04(8) 8_446 . ?
O6 La1 O3 127.8 . 8_446 ?
O6 La1 O3 136.99(8) . . ?
O6 La1 O3 127.8 8_446 . ?
O6 La1 O3 136.99(8) 8_446 8_446 ?
O6 La1 O6 67.29(10) 8_446 . ?
La1 O1 La1 166.0(2) . 6_654 ?
C1 O1 La1 97.01(11) . . ?
C1 O1 La1 97.01(10) . 6_654 ?
O1 C1 La1 59.16(12) . 6_654 ?
O1 C1 N1 116.5(3) . . ?
O1 C1 N1 116.5(3) . 6_654 ?
N1 C1 La1 170.2(3) . 6_654 ?
N1 C1 La1 58.2(3) 6_654 6_654 ?
N1 C1 N1 126.9(7) . 6_654 ?
C1 N1 La1 96.3(4) . . ?
C2 N1 La1 145.0(4) . . ?
C2 N1 C1 117.7(5) . . ?
N1 C2 N3 117.8(5) . . ?
N2 C2 N1 121.9(5) . . ?
N2 C2 N3 120.3(5) . . ?
C2 N2 C3 119.2(5) . . ?
N2 C3 N4 122.8(5) . . ?
O2 C3 N2 118.9(5) . . ?
O2 C3 N4 118.3(5) . . ?
C2 N3 C2 122.1(7) 6_654 . ?
C4 N3 C2 119.0(4) . 6_654 ?
C4 N3 C2 119.0(4) . . ?
N4 C4 N3 120.0(3) 6_654 . ?
N4 C4 N3 120.0(3) . . ?
N4 C4 N4 120.1(7) . 6_654 ?
C4 N4 C3 118.6(4) . . ?
La1 O4 H4A 112.2 . . ?
La1 O4 H4B 107.6 . . ?
H4A O4 H4B 99.3 . . ?
La1 O3 H3A 126.4 . . ?
La1 O3 H3B 129.1 . . ?
H3A O3 H3B 96.4 . . ?
H5A O5 H5A 92.9 . 6_644 ?
H5A O5 H5B 143.4 . 6_644 ?
H5A O5 H5B 99.4 6_644 6_644 ?
H5A O5 H5B 99.4 . . ?
H5B O5 H5A 143.4 . 6_644 ?
H5B O5 H5B 90.9 . 6_644 ?
La1 O6 H6A 97.6 . . ?
La1 O6 H6B 127.1 . . ?
H6A O6 H6B 100.0 . . ?

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 0.85 2.18 2.9036(12) 143.5 3_756 yes
O4 H4B O2 0.85 1.91 2.717(4) 156.7 2_755 yes
O6 H6A O1 0.85 2.52 3.011(2) 117.5 . yes
O6 H6B N4 0.85 1.91 2.751(4) 167.7 7_745 yes
O5 H5A O4 0.85 2.45 2.733(3) 99.9 8_446 yes
O5 H5A O4 0.85 2.37 2.733(4) 106.5 3_746 yes
O5 H5B N2 0.85 2.37 2.960(5) 126.6 . yes
O5 H5B O2 0.85 2.13 2.959 166.4 . yes
O3 H3A O2 0.87 1.90 2.748(5) 165.3 7_645 yes
O3 H3B O6 0.88 2.16 2.974(3) 153.5 8_346 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
La1 O1 C1 La1 180.000(1) . . . 6_654 ?
La1 O1 C1 N1 -170.0(3) 6_654 . . . ?
La1 O1 C1 N1 10.0(3) 6_654 . . 6_654 ?
La1 O1 C1 N1 -170.0(3) . . . 6_654 ?
La1 O1 C1 N1 10.0(3) . . . . ?
La1 N1 C2 N2 17.2(13) . . . . ?
La1 N1 C2 N3 -162.1(5) . . . . ?
O1 C1 N1 La1 -10.1(3) . . . . ?
O1 C1 N1 C2 178.6(5) . . . . ?
C1 N1 C2 N2 -178.1(5) . . . . ?
C1 N1 C2 N3 2.6(9) . . . . ?
N1 C1 N1 La1 169.9(3) 6_654 . . . ?
N1 C1 N1 C2 -1.4(5) 6_654 . . . ?
N1 C2 N2 C3 178.9(6) . . . . ?
N1 C2 N3 C2 -1.3(5) . . . 6_654 ?
N1 C2 N3 C4 178.7(5) . . . . ?
C2 N2 C3 N4 4.0(10) . . . . ?
C2 N2 C3 O2 -176.0(5) . . . . ?
C2 N3 C4 N4 -178.8(4) . . . 6_654 ?
C2 N3 C4 N4 1.2(4) 6_654 . . 6_654 ?
C2 N3 C4 N4 -178.8(4) 6_654 . . . ?
C2 N3 C4 N4 1.2(4) . . . . ?
N2 C2 N3 C2 179.3(7) . . . 6_654 ?
N2 C2 N3 C4 -0.7(7) . . . . ?
N2 C3 N4 C4 -3.5(8) . . . . ?
N3 C2 N2 C3 -1.8(9) . . . . ?
N3 C4 N4 C3 0.8(5) . . . . ?
N4 C4 N4 C3 -179.2(5) 6_654 . . . ?
O2 C3 N4 C4 176.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.583(14)
2 0.417(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_tb-cy
_database_code_depnum_ccdc_archive 'CCDC 2178359'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2022-06-10 deposited with the CCDC.	2022-09-01 downloaded from the CCDC.
;
_audit_creation_date             2022-03-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H14 N7 O10 Tb'
_chemical_formula_sum            'C6 H14 N7 O10 Tb'
_chemical_formula_weight         503.16
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -9.1472 9.1891 '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                   11.8582(4)
_cell_length_b                   6.8416(2)
_cell_length_c                   16.6967(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.700(1)
_cell_angle_gamma                90
_cell_volume                     1351.76(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9921
_cell_measurement_temperature    298
_cell_measurement_theta_max      70.08
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   0.299
_shelx_estimated_absorpt_T_min   0.058
_exptl_absorpt_coefficient_mu    26.484
_exptl_absorpt_correction_T_max  0.1348
_exptl_absorpt_correction_T_min  0.0262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1647 before and 0.0586 after correction.
The Ratio of minimum to maximum transmission is 0.1944.
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    2.472
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_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  0.0402
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_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            24483
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.137
_diffrn_reflns_theta_min         4.441
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           0.65
_diffrn_source_power             0.029119999999999997
_diffrn_source_voltage           44.8
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2441
_reflns_number_total             2561
_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) V8.40A; 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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         2561
_refine_ls_number_restraints     112
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0248
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+0.3202P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0616
_refine_ls_wR_factor_ref         0.0626
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 H4A-H4B \\sim H5A-H5B \\sim H6A-H6B \\sim H7A-H7B \\sim H8A-H8B \\sim H9A-H9B
\\sim H10A-H10B
 with sigma of 0.02
 O4-H4A \\sim O4-H4B \\sim O5-H5A \\sim O5-H5B \\sim O6-H6A \\sim O6-H6B \\sim
O7-H7A \\sim O7-H7B \\sim O8-
 H8A \\sim O8-H8B \\sim O9-H9A \\sim O9-H9B \\sim O10-H10A \\sim O10-H10B
 with sigma of 0.02
;
_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
Tb1 Tb 0.51911(2) 0.63841(2) 0.17683(2) 0.03578(8) Uani 1 1 d . . . . .
O1 O 0.6653(2) 0.7703(4) 0.27100(14) 0.0480(5) Uani 1 1 d . . . . .
O2 O 0.17860(19) 0.5928(3) 0.44950(15) 0.0444(5) Uani 1 1 d . . . . .
O3 O 0.6504(2) 0.8553(3) 0.67706(14) 0.0460(5) Uani 1 1 d . . . . .
O4 O 0.6019(2) 0.3526(4) 0.24592(17) 0.0497(6) Uani 1 1 d D . . . .
H4A H 0.580(4) 0.316(8) 0.286(2) 0.075 Uiso 1 1 d D U . . .
H4B H 0.6662(18) 0.334(7) 0.247(3) 0.075 Uiso 1 1 d D U . . .
O5 O 0.6804(2) 0.5886(4) 0.10785(16) 0.0474(5) Uani 1 1 d D . . . .
H5A H 0.716(3) 0.491(4) 0.109(3) 0.071 Uiso 1 1 d D U . . .
H5B H 0.721(3) 0.669(5) 0.092(3) 0.071 Uiso 1 1 d D U . . .
O6 O 0.5004(2) 0.3507(3) 0.08676(16) 0.0468(5) Uani 1 1 d D . . . .
H6A H 0.528(4) 0.340(7) 0.0455(19) 0.070 Uiso 1 1 d D U . . .
H6B H 0.442(2) 0.299(7) 0.082(3) 0.070 Uiso 1 1 d D U . . .
O7 O 0.5858(2) 0.9389(4) 0.10944(18) 0.0565(6) Uani 1 1 d D . . . .
H7A H 0.580(5) 1.037(5) 0.132(3) 0.085 Uiso 1 1 d D U . . .
H7B H 0.620(5) 0.954(8) 0.072(2) 0.085 Uiso 1 1 d D U . . .
O8 O 0.3939(2) 0.7103(3) 0.05610(14) 0.0427(5) Uani 1 1 d D . . . .
H8A H 0.335(2) 0.660(5) 0.052(3) 0.064 Uiso 1 1 d D U . . .
H8B H 0.383(4) 0.822(3) 0.049(3) 0.064 Uiso 1 1 d D U . . .
O9 O 0.3534(2) 0.4620(4) 0.20241(15) 0.0464(5) Uani 1 1 d D . . . .
H9A H 0.294(2) 0.510(7) 0.195(3) 0.070 Uiso 1 1 d D U . . .
H9B H 0.350(4) 0.394(6) 0.240(2) 0.070 Uiso 1 1 d D U . . .
O10 O 0.4003(2) 0.9150(4) 0.20013(15) 0.0516(6) Uani 1 1 d D . . . .
H10A H 0.371(4) 0.979(6) 0.167(2) 0.077 Uiso 1 1 d D U . . .
H10B H 0.396(5) 0.968(7) 0.2411(16) 0.077 Uiso 1 1 d D U . . .
N1 N 0.5069(2) 0.6942(4) 0.32678(15) 0.0402(5) Uani 1 1 d . . . . .
N2 N 0.3390(2) 0.6326(4) 0.38603(18) 0.0419(6) Uani 1 1 d . . . . .
N3 N 0.6721(2) 0.7971(4) 0.40689(16) 0.0400(5) Uani 1 1 d . . . . .
N4 N 0.5000(2) 0.7357(3) 0.46604(15) 0.0362(5) Uani 1 1 d . . . . .
N5 N 0.3311(2) 0.6812(4) 0.52837(16) 0.0403(5) Uani 1 1 d . . . . .
N6 N 0.6623(2) 0.8386(4) 0.54271(17) 0.0398(5) Uani 1 1 d . . . . .
N7 N 0.4892(2) 0.7750(4) 0.60549(15) 0.0403(5) Uani 1 1 d . . . . .
C1 C 0.6164(3) 0.7552(4) 0.33571(19) 0.0399(6) Uani 1 1 d . . . . .
C2 C 0.4463(3) 0.6859(4) 0.39116(18) 0.0368(6) Uani 1 1 d . . . . .
C3 C 0.2828(3) 0.6361(4) 0.4542(2) 0.0402(7) Uani 1 1 d . . . . .
C4 C 0.6140(3) 0.7911(4) 0.47198(18) 0.0368(6) Uani 1 1 d . . . . .
C5 C 0.4385(3) 0.7307(4) 0.53476(18) 0.0373(6) Uani 1 1 d . . . . .
C6 C 0.6009(3) 0.8233(4) 0.60929(19) 0.0383(6) 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
Tb1 O1 2.438(2) . ?
Tb1 O4 2.444(2) . ?
Tb1 O5 2.320(2) . ?
Tb1 O6 2.478(2) . ?
Tb1 O7 2.497(2) . ?
Tb1 O8 2.475(2) . ?
Tb1 O9 2.368(2) . ?
Tb1 O10 2.406(2) . ?
Tb1 N1 2.546(3) . ?
O1 C1 1.263(4) . ?
O2 C3 1.268(4) . ?
O3 C6 1.259(4) . ?
O4 H4A 0.777(19) . ?
O4 H4B 0.772(19) . ?
O5 H5A 0.789(19) . ?
O5 H5B 0.787(19) . ?
O6 H6A 0.785(19) . ?
O6 H6B 0.776(19) . ?
O7 H7A 0.77(2) . ?
O7 H7B 0.77(2) . ?
O8 H8A 0.781(19) . ?
O8 H8B 0.787(19) . ?
O9 H9A 0.781(19) . ?
O9 H9B 0.779(19) . ?
O10 H10A 0.77(2) . ?
O10 H10B 0.78(2) . ?
N1 C1 1.362(4) . ?
N1 C2 1.332(4) . ?
N2 C2 1.321(4) . ?
N2 C3 1.356(5) . ?
N3 C1 1.353(4) . ?
N3 C4 1.325(4) . ?
N4 C2 1.408(4) . ?
N4 C4 1.401(4) . ?
N4 C5 1.399(4) . ?
N5 C3 1.366(4) . ?
N5 C5 1.315(4) . ?
N6 C4 1.319(4) . ?
N6 C6 1.371(4) . ?
N7 C5 1.326(4) . ?
N7 C6 1.363(4) . ?

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 Tb1 O4 75.19(9) . . ?
O1 Tb1 O6 135.86(9) . . ?
O1 Tb1 O7 75.69(9) . . ?
O1 Tb1 O8 144.72(8) . . ?
O1 Tb1 N1 52.64(8) . . ?
O4 Tb1 O6 70.63(9) . . ?
O4 Tb1 O7 137.93(9) . . ?
O4 Tb1 O8 138.18(9) . . ?
O4 Tb1 N1 72.69(9) . . ?
O5 Tb1 O1 78.45(9) . . ?
O5 Tb1 O4 78.34(9) . . ?
O5 Tb1 O6 68.07(9) . . ?
O5 Tb1 O7 66.55(9) . . ?
O5 Tb1 O8 95.47(9) . . ?
O5 Tb1 O9 137.27(9) . . ?
O5 Tb1 O10 134.89(9) . . ?
O5 Tb1 N1 127.67(9) . . ?
O6 Tb1 O7 113.53(9) . . ?
O6 Tb1 N1 135.02(9) . . ?
O7 Tb1 N1 111.06(10) . . ?
O8 Tb1 O6 68.79(8) . . ?
O8 Tb1 O7 70.13(9) . . ?
O8 Tb1 N1 134.59(8) . . ?
O9 Tb1 O1 129.52(8) . . ?
O9 Tb1 O4 79.61(9) . . ?
O9 Tb1 O6 70.23(9) . . ?
O9 Tb1 O7 142.34(9) . . ?
O9 Tb1 O8 77.70(8) . . ?
O9 Tb1 O10 82.56(9) . . ?
O9 Tb1 N1 78.39(9) . . ?
O10 Tb1 O1 90.23(9) . . ?
O10 Tb1 O4 140.78(9) . . ?
O10 Tb1 O6 133.83(9) . . ?
O10 Tb1 O7 68.34(10) . . ?
O10 Tb1 O8 69.42(8) . . ?
O10 Tb1 N1 69.63(9) . . ?
C1 O1 Tb1 100.04(19) . . ?
Tb1 O4 H4A 122(4) . . ?
Tb1 O4 H4B 120(3) . . ?
H4A O4 H4B 108(3) . . ?
Tb1 O5 H5A 124(3) . . ?
Tb1 O5 H5B 127(3) . . ?
H5A O5 H5B 105(3) . . ?
Tb1 O6 H6A 125(3) . . ?
Tb1 O6 H6B 118(4) . . ?
H6A O6 H6B 107(3) . . ?
Tb1 O7 H7A 117(4) . . ?
Tb1 O7 H7B 132(4) . . ?
H7A O7 H7B 110(3) . . ?
Tb1 O8 H8A 118(4) . . ?
Tb1 O8 H8B 114(4) . . ?
H8A O8 H8B 106(3) . . ?
Tb1 O9 H9A 120(4) . . ?
Tb1 O9 H9B 122(4) . . ?
H9A O9 H9B 107(3) . . ?
Tb1 O10 H10A 125(4) . . ?
Tb1 O10 H10B 125(4) . . ?
H10A O10 H10B 109(3) . . ?
C1 N1 Tb1 92.26(18) . . ?
C2 N1 Tb1 148.7(2) . . ?
C2 N1 C1 119.0(3) . . ?
C2 N2 C3 117.7(3) . . ?
C4 N3 C1 117.6(3) . . ?
C4 N4 C2 120.5(3) . . ?
C5 N4 C2 119.5(3) . . ?
C5 N4 C4 120.0(3) . . ?
C5 N5 C3 118.6(3) . . ?
C4 N6 C6 119.0(3) . . ?
C5 N7 C6 118.7(3) . . ?
O1 C1 N1 114.7(3) . . ?
O1 C1 N3 120.6(3) . . ?
N3 C1 N1 124.7(3) . . ?
N1 C2 N4 118.0(3) . . ?
N2 C2 N1 121.8(3) . . ?
N2 C2 N4 120.2(3) . . ?
O2 C3 N2 118.3(3) . . ?
O2 C3 N5 117.3(3) . . ?
N2 C3 N5 124.4(3) . . ?
N3 C4 N4 120.1(3) . . ?
N6 C4 N3 120.5(3) . . ?
N6 C4 N4 119.4(3) . . ?
N5 C5 N4 119.5(3) . . ?
N5 C5 N7 120.8(3) . . ?
N7 C5 N4 119.6(3) . . ?
O3 C6 N6 118.3(3) . . ?
O3 C6 N7 118.6(3) . . ?
N7 C6 N6 123.1(3) . . ?

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 N7 0.777(19) 2.13(2) 2.904(4) 176(5) 3_666 yes
O4 H4B O1 0.772(19) 2.08(2) 2.849(4) 171(5) 2_645 yes
O5 H5A N3 0.789(19) 1.91(2) 2.674(4) 164(5) 2_645 yes
O5 H5B N5 0.787(19) 2.02(2) 2.783(4) 165(5) 4_675 yes
O6 H6A O8 0.785(19) 2.01(2) 2.797(4) 174(5) 3_665 yes
O6 H6B O2 0.776(19) 2.06(3) 2.796(3) 160(5) 2_545 yes
O7 H7A O6 0.77(2) 2.44(5) 3.009(4) 131(5) 1_565 yes
O7 H7B O2 0.77(2) 2.23(2) 2.961(4) 159(5) 4_675 yes
O8 H8A N6 0.781(19) 2.04(3) 2.762(4) 153(4) 4_575 yes
O8 H8B O2 0.787(19) 1.99(2) 2.754(3) 164(5) 2 yes
O9 H9A O3 0.781(19) 1.94(2) 2.722(3) 176(5) 4_575 yes
O9 H9B O3 0.779(19) 2.20(2) 2.962(3) 166(5) 3_666 yes
O10 H10A O2 0.77(2) 2.14(2) 2.880(3) 161(5) 2 yes
O10 H10B O3 0.78(2) 1.93(3) 2.682(3) 162(5) 3_676 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
Tb1 O1 C1 N1 -5.6(3) . . . . ?
Tb1 O1 C1 N3 174.1(3) . . . . ?
Tb1 N1 C1 O1 5.3(3) . . . . ?
Tb1 N1 C1 N3 -174.4(3) . . . . ?
Tb1 N1 C2 N2 -3.8(6) . . . . ?
Tb1 N1 C2 N4 176.2(3) . . . . ?
C1 N1 C2 N2 178.3(3) . . . . ?
C1 N1 C2 N4 -1.7(4) . . . . ?
C1 N3 C4 N4 2.3(4) . . . . ?
C1 N3 C4 N6 -177.1(3) . . . . ?
C2 N1 C1 O1 -175.8(3) . . . . ?
C2 N1 C1 N3 4.5(5) . . . . ?
C2 N2 C3 O2 177.3(3) . . . . ?
C2 N2 C3 N5 -3.5(4) . . . . ?
C2 N4 C4 N3 0.1(4) . . . . ?
C2 N4 C4 N6 179.5(3) . . . . ?
C2 N4 C5 N5 -0.6(4) . . . . ?
C2 N4 C5 N7 179.1(3) . . . . ?
C3 N2 C2 N1 -177.3(3) . . . . ?
C3 N2 C2 N4 2.7(4) . . . . ?
C3 N5 C5 N4 -0.1(4) . . . . ?
C3 N5 C5 N7 -179.8(3) . . . . ?
C4 N3 C1 O1 175.6(3) . . . . ?
C4 N3 C1 N1 -4.8(5) . . . . ?
C4 N4 C2 N1 -0.4(4) . . . . ?
C4 N4 C2 N2 179.6(3) . . . . ?
C4 N4 C5 N5 179.0(3) . . . . ?
C4 N4 C5 N7 -1.3(4) . . . . ?
C4 N6 C6 O3 174.9(3) . . . . ?
C4 N6 C6 N7 -5.0(4) . . . . ?
C5 N4 C2 N1 179.3(3) . . . . ?
C5 N4 C2 N2 -0.8(4) . . . . ?
C5 N4 C4 N3 -179.6(3) . . . . ?
C5 N4 C4 N6 -0.1(4) . . . . ?
C5 N5 C3 O2 -178.6(3) . . . . ?
C5 N5 C3 N2 2.2(4) . . . . ?
C5 N7 C6 O3 -176.3(3) . . . . ?
C5 N7 C6 N6 3.6(4) . . . . ?
C6 N6 C4 N3 -177.4(3) . . . . ?
C6 N6 C4 N4 3.1(4) . . . . ?
C6 N7 C5 N4 -0.5(4) . . . . ?
C6 N7 C5 N5 179.3(3) . . . . ?

_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_eu-cy
_database_code_depnum_ccdc_archive 'CCDC 2178362'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2022-06-10 deposited with the CCDC.	2022-09-01 downloaded from the CCDC.
;
_audit_creation_date             2022-03-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H14 Eu N7 O10'
_chemical_formula_sum            'C6 H14 Eu N7 O10'
_chemical_formula_weight         496.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -8.9294 11.1857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   11.8872(6)
_cell_length_b                   6.8605(3)
_cell_length_c                   16.7718(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.608(2)
_cell_angle_gamma                90
_cell_volume                     1365.07(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    295
_cell_measurement_theta_max      70.317
_cell_measurement_theta_min      4.431
_shelx_estimated_absorpt_T_max   0.284
_shelx_estimated_absorpt_T_min   0.038
_exptl_absorpt_coefficient_mu    33.639
_exptl_absorpt_correction_T_max  0.1348
_exptl_absorpt_correction_T_min  0.0191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1836 before and 0.0631 after correction.
The Ratio of minimum to maximum transmission is 0.1417.
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    2.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.05
_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  0.0440
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_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            23809
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.695
_diffrn_reflns_theta_min         4.430
_diffrn_ambient_temperature      295
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2510
_reflns_number_total             2598
_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 (2017) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2017) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.886
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         2598
_refine_ls_number_restraints     113
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0774
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 H6A-H7A_$6
 2.22 with sigma of 0.02
 O4-H4A \\sim O4-H4B \\sim O5-H5A \\sim O5-H5B \\sim O6-H6A \\sim O6-H6B \\sim
O7-H7A \\sim O7-H7B \\sim O8-
 H8A \\sim O8-H8B \\sim O9-H9A \\sim O9-H9B \\sim O10-H10A \\sim O10-H10B
 with sigma of 0.02
 H4A-H4B \\sim H5A-H5B \\sim H6A-H6B \\sim H7A-H7B \\sim H8A-H8B \\sim H9A-H9B
\\sim H10A-H10B
 with sigma of 0.02
;
_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
Eu1 Eu 0.51897(2) 0.63787(2) 0.17671(2) 0.03567(10) Uani 1 1 d . . . . .
O1 O 0.6663(2) 0.7678(4) 0.27190(14) 0.0504(6) Uani 1 1 d . . . . .
O2 O 0.17940(19) 0.5930(4) 0.44933(16) 0.0466(5) Uani 1 1 d . . . . .
O3 O 0.6490(2) 0.8566(4) 0.67594(16) 0.0490(6) Uani 1 1 d . . . . .
N1 N 0.5075(2) 0.6930(5) 0.32751(16) 0.0423(5) Uani 1 1 d . . . . .
N2 N 0.3398(3) 0.6316(4) 0.3861(2) 0.0437(6) Uani 1 1 d . . . . .
N3 N 0.6719(2) 0.7954(4) 0.40713(17) 0.0429(5) Uani 1 1 d . . . . .
N4 N 0.4999(2) 0.7359(4) 0.46563(15) 0.0381(5) Uani 1 1 d . . . . .
N5 N 0.3308(2) 0.6811(4) 0.52765(17) 0.0417(5) Uani 1 1 d . . . . .
N6 N 0.6617(2) 0.8381(4) 0.54235(19) 0.0415(6) Uani 1 1 d . . . . .
N7 N 0.4887(2) 0.7768(4) 0.60489(16) 0.0415(5) Uani 1 1 d . . . . .
C1 C 0.6172(3) 0.7531(5) 0.33625(19) 0.0411(6) Uani 1 1 d . . . . .
C2 C 0.4468(3) 0.6849(5) 0.39175(19) 0.0378(6) Uani 1 1 d . . . . .
C3 C 0.2836(3) 0.6356(4) 0.4544(2) 0.0416(7) Uani 1 1 d . . . . .
C4 C 0.6136(2) 0.7908(4) 0.47194(18) 0.0380(6) Uani 1 1 d . . . . .
C5 C 0.4387(2) 0.7308(4) 0.53445(18) 0.0373(6) Uani 1 1 d . . . . .
C6 C 0.6000(3) 0.8233(5) 0.6085(2) 0.0412(6) Uani 1 1 d . . . . .
O4 O 0.6819(2) 0.5875(4) 0.10712(17) 0.0493(5) Uani 1 1 d D . . . .
H4A H 0.717(4) 0.480(4) 0.105(3) 0.073(15) Uiso 1 1 d D . . . .
H4B H 0.730(3) 0.669(5) 0.092(3) 0.054(12) Uiso 1 1 d D . . . .
O5 O 0.5875(2) 0.9410(4) 0.1096(2) 0.0597(7) Uani 1 1 d D . . . .
H5A H 0.625(5) 0.948(8) 0.069(3) 0.090 Uiso 1 1 d D U . . .
H5B H 0.572(5) 1.057(4) 0.121(4) 0.090 Uiso 1 1 d D U . . .
O6 O 0.39240(19) 0.7121(4) 0.05563(14) 0.0446(5) Uani 1 1 d D . . . .
H6A H 0.382(4) 0.833(3) 0.048(2) 0.067 Uiso 1 1 d D U . . .
H6B H 0.327(2) 0.665(6) 0.050(4) 0.067 Uiso 1 1 d D U . . .
O7 O 0.4991(2) 0.3499(4) 0.08553(17) 0.0489(6) Uani 1 1 d D . . . .
H7A H 0.529(4) 0.337(7) 0.041(2) 0.073 Uiso 1 1 d D U . . .
H7B H 0.438(3) 0.288(8) 0.077(3) 0.073 Uiso 1 1 d D U . . .
O8 O 0.4004(2) 0.9192(4) 0.20004(15) 0.0541(6) Uani 1 1 d D . . . .
H8A H 0.370(5) 0.990(7) 0.164(2) 0.081 Uiso 1 1 d D U . . .
H8B H 0.392(5) 0.983(8) 0.2425(19) 0.081 Uiso 1 1 d D U . . .
O9 O 0.3516(2) 0.4602(4) 0.20303(15) 0.0491(5) Uani 1 1 d D . . . .
H9A H 0.347(4) 0.382(7) 0.241(3) 0.074 Uiso 1 1 d D U . . .
H9B H 0.286(2) 0.507(7) 0.195(3) 0.074 Uiso 1 1 d D U . . .
O10 O 0.6021(2) 0.3479(4) 0.24595(18) 0.0521(6) Uani 1 1 d D . . . .
H10A H 0.579(4) 0.302(9) 0.289(2) 0.078 Uiso 1 1 d D U . . .
H10B H 0.670(2) 0.310(8) 0.248(3) 0.078 Uiso 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Eu1 O1 2.461(2) . ?
Eu1 N1 2.569(3) . ?
Eu1 O4 2.349(2) . ?
Eu1 O5 2.524(3) . ?
Eu1 O6 2.503(2) . ?
Eu1 O7 2.500(3) . ?
Eu1 O8 2.435(3) . ?
Eu1 O9 2.398(2) . ?
Eu1 O10 2.478(3) . ?
O1 C1 1.263(4) . ?
O2 C3 1.270(4) . ?
O3 C6 1.261(4) . ?
N1 C1 1.366(4) . ?
N1 C2 1.335(4) . ?
N2 C2 1.322(4) . ?
N2 C3 1.363(5) . ?
N3 C1 1.351(4) . ?
N3 C4 1.326(4) . ?
N4 C2 1.399(4) . ?
N4 C4 1.401(4) . ?
N4 C5 1.403(4) . ?
N5 C3 1.355(5) . ?
N5 C5 1.326(4) . ?
N6 C4 1.320(4) . ?
N6 C6 1.371(4) . ?
N7 C5 1.326(4) . ?
N7 C6 1.359(4) . ?
O4 H4A 0.85(2) . ?
O4 H4B 0.85(2) . ?
O5 H5A 0.84(2) . ?
O5 H5B 0.84(2) . ?
O6 H6A 0.85(2) . ?
O6 H6B 0.84(2) . ?
O7 H7A 0.85(2) . ?
O7 H7B 0.85(2) . ?
O8 H8A 0.84(2) . ?
O8 H8B 0.85(2) . ?
O9 H9A 0.83(2) . ?
O9 H9B 0.84(2) . ?
O10 H10A 0.85(2) . ?
O10 H10B 0.84(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Eu1 N1 52.26(8) . . ?
O1 Eu1 O5 75.79(10) . . ?
O1 Eu1 O6 145.03(9) . . ?
O1 Eu1 O7 135.96(10) . . ?
O1 Eu1 O10 74.95(10) . . ?
O4 Eu1 O1 78.48(9) . . ?
O4 Eu1 N1 127.40(10) . . ?
O4 Eu1 O5 66.45(9) . . ?
O4 Eu1 O6 95.69(9) . . ?
O4 Eu1 O7 68.22(9) . . ?
O4 Eu1 O8 134.41(10) . . ?
O4 Eu1 O9 137.43(9) . . ?
O4 Eu1 O10 78.34(9) . . ?
O5 Eu1 N1 110.87(10) . . ?
O6 Eu1 N1 134.61(8) . . ?
O6 Eu1 O5 70.41(10) . . ?
O7 Eu1 N1 135.20(10) . . ?
O7 Eu1 O5 113.52(10) . . ?
O7 Eu1 O6 68.64(9) . . ?
O8 Eu1 O1 90.23(10) . . ?
O8 Eu1 N1 70.01(9) . . ?
O8 Eu1 O5 67.97(10) . . ?
O8 Eu1 O6 69.19(8) . . ?
O8 Eu1 O7 133.71(10) . . ?
O8 Eu1 O10 141.14(10) . . ?
O9 Eu1 O1 129.00(8) . . ?
O9 Eu1 N1 78.32(9) . . ?
O9 Eu1 O5 142.72(9) . . ?
O9 Eu1 O6 77.85(8) . . ?
O9 Eu1 O7 70.33(9) . . ?
O9 Eu1 O8 83.00(10) . . ?
O9 Eu1 O10 79.43(9) . . ?
O10 Eu1 N1 72.62(10) . . ?
O10 Eu1 O5 137.76(10) . . ?
O10 Eu1 O6 138.20(9) . . ?
O10 Eu1 O7 70.84(10) . . ?
C1 O1 Eu1 100.19(19) . . ?
C1 N1 Eu1 92.32(18) . . ?
C2 N1 Eu1 148.6(2) . . ?
C2 N1 C1 119.1(3) . . ?
C2 N2 C3 117.0(3) . . ?
C4 N3 C1 118.0(3) . . ?
C2 N4 C4 120.9(3) . . ?
C2 N4 C5 119.6(3) . . ?
C4 N4 C5 119.5(3) . . ?
C5 N5 C3 118.7(3) . . ?
C4 N6 C6 118.8(3) . . ?
C5 N7 C6 118.4(3) . . ?
O1 C1 N1 115.0(3) . . ?
O1 C1 N3 120.8(3) . . ?
N3 C1 N1 124.3(3) . . ?
N1 C2 N4 117.9(3) . . ?
N2 C2 N1 121.3(3) . . ?
N2 C2 N4 120.8(3) . . ?
O2 C3 N2 117.8(3) . . ?
O2 C3 N5 117.4(3) . . ?
N5 C3 N2 124.8(3) . . ?
N3 C4 N4 119.7(3) . . ?
N6 C4 N3 120.6(3) . . ?
N6 C4 N4 119.7(3) . . ?
N5 C5 N4 119.0(3) . . ?
N5 C5 N7 120.9(3) . . ?
N7 C5 N4 120.0(3) . . ?
O3 C6 N6 118.1(3) . . ?
O3 C6 N7 118.4(3) . . ?
N7 C6 N6 123.4(3) . . ?
Eu1 O4 H4A 125(3) . . ?
Eu1 O4 H4B 130(3) . . ?
H4A O4 H4B 102(3) . . ?
Eu1 O5 H5A 128(4) . . ?
Eu1 O5 H5B 127(4) . . ?
H5A O5 H5B 105(3) . . ?
Eu1 O6 H6A 114(3) . . ?
Eu1 O6 H6B 121(4) . . ?
H6A O6 H6B 103(3) . . ?
Eu1 O7 H7A 126(3) . . ?
Eu1 O7 H7B 123(4) . . ?
H7A O7 H7B 102(3) . . ?
Eu1 O8 H8A 125(4) . . ?
Eu1 O8 H8B 130(4) . . ?
H8A O8 H8B 104(3) . . ?
Eu1 O9 H9A 124(4) . . ?
Eu1 O9 H9B 123(4) . . ?
H9A O9 H9B 105(3) . . ?
Eu1 O10 H10A 124(4) . . ?
Eu1 O10 H10B 128(4) . . ?
H10A O10 H10B 102(3) . . ?

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 N3 0.85(2) 1.85(3) 2.673(4) 163(4) 2_645 yes
O4 H4B N5 0.85(2) 1.95(3) 2.779(4) 163(5) 4_675 yes
O5 H5A O2 0.84(2) 2.16(3) 2.974(4) 162(6) 4_675 yes
O5 H5B O7 0.84(2) 2.25(4) 3.014(4) 151(6) 1_565 yes
O6 H6A O2 0.85(2) 1.93(2) 2.748(4) 162(3) 2 yes
O6 H6B N6 0.84(2) 1.96(3) 2.759(4) 158(4) 4_575 yes
O7 H7A O6 0.85(2) 1.95(2) 2.799(4) 175(5) 3_665 yes
O7 H7B O2 0.85(2) 1.96(3) 2.792(4) 166(6) 2_545 yes
O8 H8A O2 0.84(2) 2.07(3) 2.881(4) 160(5) 2 yes
O8 H8B O3 0.85(2) 1.85(3) 2.682(4) 169(5) 3_676 yes
O9 H9A O3 0.83(2) 2.15(2) 2.974(4) 169(5) 3_666 yes
O9 H9B O3 0.84(2) 1.89(2) 2.729(4) 173(5) 4_575 yes
O10 H10A N7 0.85(2) 2.07(2) 2.914(4) 172(5) 3_666 yes
O10 H10B O1 0.84(2) 2.02(2) 2.842(4) 165(5) 2_645 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
Eu1 O1 C1 N1 -5.3(3) . . . . ?
Eu1 O1 C1 N3 174.9(3) . . . . ?
Eu1 N1 C1 O1 5.0(3) . . . . ?
Eu1 N1 C1 N3 -175.2(3) . . . . ?
Eu1 N1 C2 N2 -3.2(7) . . . . ?
Eu1 N1 C2 N4 177.2(3) . . . . ?
C1 N1 C2 N2 178.6(3) . . . . ?
C1 N1 C2 N4 -1.0(5) . . . . ?
C1 N3 C4 N4 2.4(5) . . . . ?
C1 N3 C4 N6 -177.4(3) . . . . ?
C2 N1 C1 O1 -175.9(3) . . . . ?
C2 N1 C1 N3 3.9(5) . . . . ?
C2 N2 C3 O2 177.0(3) . . . . ?
C2 N2 C3 N5 -3.3(5) . . . . ?
C2 N4 C4 N3 0.3(4) . . . . ?
C2 N4 C4 N6 -180.0(3) . . . . ?
C2 N4 C5 N5 -1.3(4) . . . . ?
C2 N4 C5 N7 179.2(3) . . . . ?
C3 N2 C2 N1 -177.3(3) . . . . ?
C3 N2 C2 N4 2.3(5) . . . . ?
C3 N5 C5 N4 0.5(5) . . . . ?
C3 N5 C5 N7 180.0(3) . . . . ?
C4 N3 C1 O1 175.2(3) . . . . ?
C4 N3 C1 N1 -4.6(5) . . . . ?
C4 N4 C2 N1 -1.0(5) . . . . ?
C4 N4 C2 N2 179.4(3) . . . . ?
C4 N4 C5 N5 179.1(3) . . . . ?
C4 N4 C5 N7 -0.4(4) . . . . ?
C4 N6 C6 O3 175.4(3) . . . . ?
C4 N6 C6 N7 -5.4(5) . . . . ?
C5 N4 C2 N1 179.4(3) . . . . ?
C5 N4 C2 N2 -0.2(5) . . . . ?
C5 N4 C4 N3 179.9(3) . . . . ?
C5 N4 C4 N6 -0.4(4) . . . . ?
C5 N5 C3 O2 -178.4(3) . . . . ?
C5 N5 C3 N2 1.9(5) . . . . ?
C5 N7 C6 O3 -176.2(3) . . . . ?
C5 N7 C6 N6 4.6(5) . . . . ?
C6 N6 C4 N3 -177.1(3) . . . . ?
C6 N6 C4 N4 3.1(4) . . . . ?
C6 N7 C5 N4 -1.6(4) . . . . ?
C6 N7 C5 N5 178.9(3) . . . . ?

_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_yb-cy
_database_code_depnum_ccdc_archive 'CCDC 2178363'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2022-06-10 deposited with the CCDC.	2022-09-01 downloaded from the CCDC.
;
_audit_creation_date             2022-03-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H8 N7 O7 Yb, H2 O'
_chemical_formula_sum            'C6 H10 N7 O8 Yb'
_chemical_formula_weight         481.25
_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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Yb Yb -7.2108 4.4329 '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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   5.6782(2)
_cell_length_b                   12.0332(4)
_cell_length_c                   17.5540(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.652(2)
_cell_angle_gamma                90
_cell_volume                     1199.33(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.004
_cell_measurement_theta_min      5.040
_shelx_estimated_absorpt_T_max   0.753
_shelx_estimated_absorpt_T_min   0.276
_exptl_absorpt_coefficient_mu    15.071
_exptl_absorpt_correction_T_max  0.2260
_exptl_absorpt_correction_T_min  0.0921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1309 before and 0.0385 after correction. The Ratio of minimum to maximum transmission is 0.4075. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear Colorless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    2.665
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             916
_exptl_crystal_size_max          0.115
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_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  0.0274
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20269
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.996
_diffrn_reflns_theta_min         5.039
_diffrn_ambient_temperature      100.00
_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 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.973
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                2303
_reflns_number_total             2318
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.097
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.123
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.197(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2318
_refine_ls_number_restraints     53
_refine_ls_R_factor_all          0.0206
_refine_ls_R_factor_gt           0.0204
_refine_ls_restrained_S_all      3.765
_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)+(0.0422P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0509
_refine_ls_wR_factor_ref         0.0510
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.803(15)
 0.197(15)
2. Fixed Uiso
 At 1.5 times of:
  All O(H,H,H,H,H,H,H,H,H,H) groups
3. Restrained distances
 H4A-H4B = H5A-H5B = H6A-H6B = H7A-H7B = H8A-H8B
 1.28 with sigma of 0.002
 H4A-H5B
 2.22 with sigma of 0.02
 O4-H4A \\sim O4-H4B \\sim O5-H5A \\sim O5-H5B \\sim O6-H6A \\sim O6-H6B \\sim
O7-H7A \\sim O7-H7B \\sim O8-
 H8A \\sim O8-H8B
 with sigma of 0.02
4.a Rotating group:
 C6(O4,O5,O6,O7,O8,H6A,H6B), O8(H5A,H5B), O8(H4A,H4B), O8(H8A,H8B), O8(H7A,H7B)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Yb1 Yb 0.38203(5) 0.36071(2) 0.66607(3) 0.01642(11) Uani 1 1 d . . . . .
O1 O 0.6780(8) 0.4844(4) 0.6241(2) 0.0192(9) Uani 1 1 d . . . . .
O3 O 0.7072(7) 0.6841(4) 0.2561(2) 0.0183(9) Uani 1 1 d . . . . .
O2 O -0.1581(8) 0.3405(4) 0.3675(3) 0.0217(8) Uani 1 1 d . . . . .
N4 N 0.4339(7) 0.4963(5) 0.4143(3) 0.0177(10) Uani 1 1 d . . . . .
N3 N 0.7241(10) 0.5559(5) 0.5036(3) 0.0212(11) Uani 1 1 d . . . . .
N1 N 0.4119(10) 0.4330(4) 0.5397(3) 0.0184(11) Uani 1 1 d . . . . .
N2 N 0.1261(14) 0.3777(5) 0.4537(4) 0.0209(14) Uani 1 1 d . . . . .
N5 N 0.1467(10) 0.4412(5) 0.3240(3) 0.0209(11) Uani 1 1 d . . . . .
N7 N 0.4483(9) 0.5558(5) 0.2884(3) 0.0185(11) Uani 1 1 d . . . . .
N6 N 0.7356(13) 0.6204(5) 0.3800(4) 0.0198(13) Uani 1 1 d . . . . .
C5 C 0.6355(10) 0.5587(5) 0.4332(3) 0.0180(11) Uani 1 1 d . . . . .
C2 C 0.3192(10) 0.4341(5) 0.4698(3) 0.0176(10) Uani 1 1 d . . . . .
C4 C 0.3409(10) 0.4962(5) 0.3409(3) 0.0186(11) Uani 1 1 d . . . . .
C1 C 0.6101(10) 0.4937(5) 0.5544(3) 0.0176(10) Uani 1 1 d . . . . .
C3 C 0.0362(11) 0.3852(5) 0.3812(4) 0.0195(11) Uani 1 1 d . . . . .
C6 C 0.6385(3) 0.62078(16) 0.30972(10) 0.0174(11) Uani 1 1 d . . . . .
O4 O 0.1130(4) 0.50552(17) 0.67519(11) 0.0197(8) Uani 1 1 d DR . . . .
O5 O 0.5997(3) 0.22079(18) 0.61127(13) 0.0187(9) Uani 1 1 d DR . . . .
O6 O 0.0750(3) 0.2912(2) 0.59607(12) 0.0209(10) Uani 1 1 d DR . . . .
O7 O 0.1686(5) 0.24685(16) 0.74260(10) 0.0199(9) Uani 1 1 d DR . . . .
O8 O 0.6498(4) 0.19462(16) 0.46590(12) 0.0223(8) Uani 1 1 d DR . . . .
H6A H -0.038309 0.257059 0.606488 0.033 Uiso 1 1 d DR U . . .
H6B H 0.057161 0.318809 0.556118 0.033 Uiso 1 1 d DR U . . .
H5A H 0.570222 0.213630 0.567719 0.033 Uiso 1 1 d DR U . . .
H5B H 0.633731 0.162900 0.628659 0.033 Uiso 1 1 d DR U . . .
H4A H -0.012072 0.498329 0.656728 0.033 Uiso 1 1 d DR U . . .
H4B H 0.103218 0.528910 0.716208 0.033 Uiso 1 1 d DR U . . .
H8A H 0.716702 0.243320 0.446269 0.033 Uiso 1 1 d DR U . . .
H8B H 0.527663 0.185360 0.445919 0.033 Uiso 1 1 d DR U . . .
H7A H 0.199858 0.202710 0.774389 0.033 Uiso 1 1 d DR U . . .
H7B H 0.033738 0.260309 0.744298 0.033 Uiso 1 1 d DR U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Yb1 O1 2.368(5) . ?
Yb1 O3 2.476(4) 2_565 ?
Yb1 N1 2.390(5) . ?
Yb1 N7 2.397(5) 2_565 ?
Yb1 C6 2.9061(19) 2_565 ?
Yb1 O4 2.324(2) . ?
Yb1 O5 2.306(2) . ?
Yb1 O6 2.280(2) . ?
Yb1 O7 2.2775(19) . ?
Yb1 H6B 2.7021 . ?
Yb1 H5A 2.7013 . ?
Yb1 H4B 2.7220 . ?
Yb1 H7B 2.7053 . ?
O1 C1 1.283(7) . ?
O3 C6 1.275(5) . ?
O2 C3 1.248(9) . ?
N4 C5 1.406(8) . ?
N4 C2 1.396(8) . ?
N4 C4 1.387(8) . ?
N3 C5 1.329(8) . ?
N3 C1 1.338(8) . ?
N1 C2 1.329(8) . ?
N1 C1 1.364(8) . ?
N2 C2 1.317(10) . ?
N2 C3 1.369(10) . ?
N5 C4 1.317(8) . ?
N5 C3 1.368(9) . ?
N7 C4 1.322(8) . ?
N7 C6 1.382(6) . ?
N6 C5 1.325(9) . ?
N6 C6 1.346(7) . ?
O4 H4A 0.7818 . ?
O4 H4B 0.7757 . ?
O5 H5A 0.7855 . ?
O5 H5B 0.7838 . ?
O6 H6A 0.7868 . ?
O6 H6B 0.7816 . ?
O7 H7A 0.7891 . ?
O7 H7B 0.7839 . ?
O8 H8A 0.7806 . ?
O8 H8B 0.7817 . ?

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 Yb1 O3 78.98(14) . 2_565 ?
O1 Yb1 N1 54.87(17) . . ?
O1 Yb1 N7 84.88(17) . 2_565 ?
O1 Yb1 C6 82.62(11) . 2_565 ?
O1 Yb1 H6B 112.1 . . ?
O1 Yb1 H5A 85.7 . . ?
O1 Yb1 H4B 92.9 . . ?
O1 Yb1 H7B 164.6 . . ?
O3 Yb1 C6 25.86(10) 2_565 2_565 ?
O3 Yb1 H6B 156.0 2_565 . ?
O3 Yb1 H5A 88.2 2_565 . ?
O3 Yb1 H4B 112.8 2_565 . ?
O3 Yb1 H7B 97.1 2_565 . ?
N1 Yb1 O3 127.68(17) . 2_565 ?
N1 Yb1 N7 131.82(16) . 2_565 ?
N1 Yb1 C6 137.50(15) . 2_565 ?
N1 Yb1 H6B 57.3 . . ?
N1 Yb1 H5A 67.2 . . ?
N1 Yb1 H4B 94.4 . . ?
N1 Yb1 H7B 133.9 . . ?
N7 Yb1 O3 53.92(16) 2_565 2_565 ?
N7 Yb1 C6 28.17(13) 2_565 2_565 ?
N7 Yb1 H6B 144.8 2_565 . ?
N7 Yb1 H5A 142.0 2_565 . ?
N7 Yb1 H4B 59.0 2_565 . ?
N7 Yb1 H7B 80.8 2_565 . ?
C6 Yb1 H6B 164.9 2_565 . ?
C6 Yb1 H5A 114.0 2_565 . ?
C6 Yb1 H4B 87.1 2_565 . ?
C6 Yb1 H7B 87.5 2_565 . ?
O4 Yb1 O1 91.13(12) . . ?
O4 Yb1 O3 127.24(11) . 2_565 ?
O4 Yb1 N1 81.07(13) . . ?
O4 Yb1 N7 73.77(14) . 2_565 ?
O4 Yb1 C6 101.89(6) . 2_565 ?
O4 Yb1 H6B 75.2 . . ?
O4 Yb1 H5A 143.2 . . ?
O4 Yb1 H4B 15.2 . . ?
O4 Yb1 H7B 79.3 . . ?
O5 Yb1 O1 86.74(12) . . ?
O5 Yb1 O3 73.02(12) . 2_565 ?
O5 Yb1 N1 80.47(13) . . ?
O5 Yb1 N7 126.92(14) . 2_565 ?
O5 Yb1 C6 98.76(7) . 2_565 ?
O5 Yb1 O4 158.79(9) . . ?
O5 Yb1 H6B 86.0 . . ?
O5 Yb1 H5A 15.6 . . ?
O5 Yb1 H4B 174.0 . . ?
O5 Yb1 H7B 106.5 . . ?
O6 Yb1 O1 127.12(11) . . ?
O6 Yb1 O3 145.50(12) . 2_565 ?
O6 Yb1 N1 72.25(15) . . ?
O6 Yb1 N7 138.40(15) . 2_565 ?
O6 Yb1 C6 150.25(7) . 2_565 ?
O6 Yb1 O4 79.22(6) . . ?
O6 Yb1 O5 85.27(6) . . ?
O6 Yb1 H6B 15.2 . . ?
O6 Yb1 H5A 73.8 . . ?
O6 Yb1 H4B 90.2 . . ?
O6 Yb1 H7B 63.3 . . ?
O7 Yb1 O1 161.02(12) . . ?
O7 Yb1 O3 83.71(12) . 2_565 ?
O7 Yb1 N1 144.10(16) . . ?
O7 Yb1 N7 78.63(14) . 2_565 ?
O7 Yb1 C6 78.40(7) . 2_565 ?
O7 Yb1 O4 93.20(9) . . ?
O7 Yb1 O5 95.63(8) . . ?
O7 Yb1 O6 71.86(7) . . ?
O7 Yb1 H6B 86.9 . . ?
O7 Yb1 H5A 101.5 . . ?
O7 Yb1 H4B 86.6 . . ?
O7 Yb1 H7B 15.2 . . ?
H6B Yb1 H5A 72.1 . . ?
H6B Yb1 H4B 88.6 . . ?
H6B Yb1 H7B 77.4 . . ?
H5A Yb1 H4B 158.4 . . ?
H5A Yb1 H7B 109.2 . . ?
H4B Yb1 H7B 74.7 . . ?
C1 O1 Yb1 98.3(4) . . ?
C6 O3 Yb1 96.3(2) . 2_564 ?
C2 N4 C5 120.5(5) . . ?
C4 N4 C5 121.3(5) . . ?
C4 N4 C2 118.2(5) . . ?
C5 N3 C1 117.0(6) . . ?
C2 N1 Yb1 145.9(4) . . ?
C2 N1 C1 119.1(5) . . ?
C1 N1 Yb1 94.9(4) . . ?
C2 N2 C3 117.8(7) . . ?
C4 N5 C3 118.2(6) . . ?
C4 N7 Yb1 141.5(4) . 2_564 ?
C4 N7 C6 118.9(5) . . ?
C6 N7 Yb1 96.9(3) . 2_564 ?
C5 N6 C6 118.2(6) . . ?
N3 C5 N4 120.3(6) . . ?
N6 C5 N4 119.2(6) . . ?
N6 C5 N3 120.5(6) . . ?
N1 C2 N4 117.8(5) . . ?
N2 C2 N4 121.3(6) . . ?
N2 C2 N1 120.8(6) . . ?
N5 C4 N4 121.2(5) . . ?
N5 C4 N7 120.4(6) . . ?
N7 C4 N4 118.3(5) . . ?
O1 C1 N3 122.9(6) . . ?
O1 C1 N1 111.8(5) . . ?
N3 C1 N1 125.3(6) . . ?
O2 C3 N2 118.0(6) . . ?
O2 C3 N5 118.9(6) . . ?
N5 C3 N2 123.0(7) . . ?
O3 C6 Yb1 57.9(2) . 2_564 ?
O3 C6 N7 112.5(3) . . ?
O3 C6 N6 123.6(4) . . ?
N7 C6 Yb1 55.0(2) . 2_564 ?
N6 C6 Yb1 172.7(3) . 2_564 ?
N6 C6 N7 123.9(4) . . ?
Yb1 O4 H4A 118.9 . . ?
Yb1 O4 H4B 112.9 . . ?
H4A O4 H4B 110.5 . . ?
Yb1 O5 H5A 112.1 . . ?
Yb1 O5 H5B 128.1 . . ?
H5A O5 H5B 109.3 . . ?
Yb1 O6 H6A 133.5 . . ?
Yb1 O6 H6B 114.7 . . ?
H6A O6 H6B 109.4 . . ?
Yb1 O7 H7A 134.9 . . ?
Yb1 O7 H7B 115.1 . . ?
H7A O7 H7B 108.9 . . ?
H8A O8 H8B 110.0 . . ?

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
O6 H6A O5 0.79 2.10 2.844 156.9 1_455 yes
O6 H6B N1 0.78 2.46 2.755(6) 104.2 . yes
O6 H6B N2 0.78 1.98 2.726(7) 160.7 . yes
O5 H5A O8 0.79 1.86 2.590 153.6 . yes
O5 H5B O4 0.78 2.07 2.824 162.5 3_545 yes
O4 H4A O1 0.78 1.85 2.631(5) 173.4 1_455 yes
O4 H4B N5 0.78 1.94 2.695(6) 164.5 2_565 yes
O4 H4B N7 0.78 2.54 2.834(6) 104.8 2_565 yes
O8 H8A O2 0.78 1.95 2.701(5) 161.1 1_655 yes
O8 H8B N3 0.78 2.54 3.017(6) 120.7 3_445 yes
O8 H8B N6 0.78 2.16 2.919(7) 164.8 3_445 yes
O7 H7A O2 0.79 1.89 2.614(5) 152.6 4 yes
O7 H7B O3 0.78 1.98 2.762(5) 171.3 2_465 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
Yb1 O1 C1 N3 -179.1(5) . . . . ?
Yb1 O1 C1 N1 0.7(5) . . . . ?
Yb1 O3 C6 N7 6.3(3) 2_564 . . . ?
Yb1 O3 C6 N6 -171.5(4) 2_564 . . . ?
Yb1 N1 C2 N4 -177.5(5) . . . . ?
Yb1 N1 C2 N2 2.1(12) . . . . ?
Yb1 N1 C1 O1 -0.7(5) . . . . ?
Yb1 N1 C1 N3 179.1(5) . . . . ?
Yb1 N7 C4 N4 -160.2(5) 2_564 . . . ?
Yb1 N7 C4 N5 17.8(10) 2_564 . . . ?
Yb1 N7 C6 O3 -6.5(3) 2_564 . . . ?
Yb1 N7 C6 N6 171.3(4) 2_564 . . . ?
C5 N4 C2 N1 -2.4(8) . . . . ?
C5 N4 C2 N2 178.0(6) . . . . ?
C5 N4 C4 N5 -177.3(5) . . . . ?
C5 N4 C4 N7 0.7(8) . . . . ?
C5 N3 C1 O1 -180.0(6) . . . . ?
C5 N3 C1 N1 0.3(9) . . . . ?
C5 N6 C6 O3 173.7(5) . . . . ?
C5 N6 C6 N7 -3.9(8) . . . . ?
C2 N4 C5 N3 2.5(9) . . . . ?
C2 N4 C5 N6 -177.4(6) . . . . ?
C2 N4 C4 N5 1.5(8) . . . . ?
C2 N4 C4 N7 179.5(5) . . . . ?
C2 N1 C1 O1 179.9(5) . . . . ?
C2 N1 C1 N3 -0.3(9) . . . . ?
C2 N2 C3 O2 -173.4(6) . . . . ?
C2 N2 C3 N5 5.0(10) . . . . ?
C4 N4 C5 N3 -178.8(5) . . . . ?
C4 N4 C5 N6 1.3(9) . . . . ?
C4 N4 C2 N1 178.8(5) . . . . ?
C4 N4 C2 N2 -0.8(8) . . . . ?
C4 N5 C3 O2 174.0(6) . . . . ?
C4 N5 C3 N2 -4.4(10) . . . . ?
C4 N7 C6 Yb1 -165.3(6) . . . 2_564 ?
C4 N7 C6 O3 -171.9(5) . . . . ?
C4 N7 C6 N6 6.0(7) . . . . ?
C1 N3 C5 N4 -1.3(9) . . . . ?
C1 N3 C5 N6 178.5(6) . . . . ?
C1 N1 C2 N4 1.3(8) . . . . ?
C1 N1 C2 N2 -179.0(5) . . . . ?
C3 N2 C2 N4 -2.3(9) . . . . ?
C3 N2 C2 N1 178.1(6) . . . . ?
C3 N5 C4 N4 1.0(9) . . . . ?
C3 N5 C4 N7 -176.9(6) . . . . ?
C6 N7 C4 N4 -4.1(8) . . . . ?
C6 N7 C4 N5 173.9(5) . . . . ?
C6 N6 C5 N4 0.2(9) . . . . ?
C6 N6 C5 N3 -179.7(5) . . . . ?

_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 0.803(15)
2 0.197(15)

####################################################################### 
# 
# 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_ho-cy
_database_code_depnum_ccdc_archive 'CCDC 2178364'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2022-06-10 deposited with the CCDC.	2022-09-01 downloaded from the CCDC.
;
_audit_creation_date             2022-03-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H8 Ho N7 O7, H2 O'
_chemical_formula_sum            'C6 H10 Ho N7 O8'
_chemical_formula_weight         473.14
_chemical_absolute_configuration unk
_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'
Ho Ho -14.9734 3.7046 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   5.7138(3)
_cell_length_b                   12.1155(7)
_cell_length_c                   17.6748(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.136(2)
_cell_angle_gamma                90
_cell_volume                     1223.31(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9209
_cell_measurement_temperature    298
_cell_measurement_theta_max      69.829
_cell_measurement_theta_min      5.005
_shelx_estimated_absorpt_T_max   0.702
_shelx_estimated_absorpt_T_min   0.516
_exptl_absorpt_coefficient_mu    12.716
_exptl_absorpt_correction_T_max  0.1348
_exptl_absorpt_correction_T_min  0.0355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1282 before and 0.0408 after correction.
The Ratio of minimum to maximum transmission is 0.2634.
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    2.569
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       fragment
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_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  0.0456
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11086
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.154
_diffrn_reflns_theta_min         5.005
_diffrn_ambient_temperature      298.15
_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 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           0.65
_diffrn_source_power             0.029119999999999997
_diffrn_source_voltage           44.8
_reflns_Friedel_coverage         0.929
_reflns_Friedel_fraction_full    0.934
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                2200
_reflns_number_total             2228
_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 (2019) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2019) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.390(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2228
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      1.046
_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)+(0.0558P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0695
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.610(13)
 0.390(13)
2. Fixed Uiso
 At 1.5 times of:
  All O(H,H,H,H,H,H,H,H,H,H) groups
3. Restrained distances
 H4B-H8B_$3
 2.2 with sigma of 0.02
 O4-H4A \\sim O4-H4B \\sim O5-H5A \\sim O5-H5B \\sim O6-H6A \\sim O6-H6B \\sim
O7-H7A \\sim O7-H7B \\sim O8-
 H8A \\sim O8-H8B
 with sigma of 0.02
 H4A-H4B \\sim H5A-H5B \\sim H6A-H6B \\sim H7A-H7B \\sim H8A-H8B
 with sigma of 0.02
4.a Rotating group:
 C6(O4,O5,O6,O7,O8,H6A,H6B), O8(H5A,H5B), O8(H4A,H4B), O8(H8A,H8B), O8(H7A,H7B)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ho1 Ho 0.61883(6) 0.36267(2) 0.33356(4) 0.04050(15) Uani 1 1 d . . . . .
O1 O 0.3245(8) 0.4884(4) 0.3767(3) 0.0463(9) Uani 1 1 d . . . . .
O2 O 0.2927(7) 0.6796(4) 0.7427(3) 0.0446(9) Uani 1 1 d . . . . .
O3 O 1.1534(9) 0.3397(4) 0.6331(3) 0.0505(9) Uani 1 1 d . . . . .
N1 N 0.5916(10) 0.4366(5) 0.4601(3) 0.0449(11) Uani 1 1 d . . . . .
N2 N 0.8730(13) 0.3795(5) 0.5471(4) 0.0454(14) Uani 1 1 d . . . . .
N3 N 0.2783(9) 0.5576(5) 0.4965(3) 0.0459(11) Uani 1 1 d . . . . .
N4 N 0.5678(7) 0.4967(4) 0.5853(3) 0.0398(10) Uani 1 1 d . . . . .
N5 N 0.8517(9) 0.4397(4) 0.6754(3) 0.0440(11) Uani 1 1 d . . . . .
N6 N 0.2668(12) 0.6186(5) 0.6198(4) 0.0444(12) Uani 1 1 d . . . . .
N7 N 0.5513(9) 0.5541(4) 0.7103(3) 0.0443(11) Uani 1 1 d . . . . .
C1 C 0.3939(10) 0.4967(5) 0.4458(4) 0.0426(11) Uani 1 1 d . . . . .
C2 C 0.6813(10) 0.4362(5) 0.5302(3) 0.0407(10) Uani 1 1 d . . . . .
C3 C 0.9620(11) 0.3854(5) 0.6190(4) 0.0433(11) Uani 1 1 d . . . . .
C4 C 0.3668(9) 0.5590(5) 0.5666(4) 0.0420(11) Uani 1 1 d . . . . .
C5 C 0.6584(10) 0.4962(5) 0.6586(3) 0.0411(11) Uani 1 1 d . . . . .
C6 C 0.3638(4) 0.61842(19) 0.68937(13) 0.0421(12) Uani 1 1 d . . . . .
O4 O 0.4031(4) 0.2200(2) 0.38948(16) 0.0489(10) Uani 1 1 d DR . . . .
O5 O 0.9295(4) 0.2923(3) 0.40558(15) 0.0518(11) Uani 1 1 d DR . . . .
O6 O 0.8348(4) 0.24667(18) 0.25752(13) 0.0536(11) Uani 1 1 d DR . . . .
O7 O 0.8924(4) 0.50707(19) 0.32340(14) 0.0458(8) Uani 1 1 d DR . . . .
O8 O -0.1450(3) 0.6978(2) 0.53438(14) 0.0585(11) Uani 1 1 d DR . . . .
H6A H 0.785319 0.208979 0.221830 0.088 Uiso 1 1 d DR U . . .
H6B H 0.969549 0.260459 0.245309 0.088 Uiso 1 1 d DR U . . .
H5A H 0.921650 0.300790 0.451879 0.088 Uiso 1 1 d DR U . . .
H5B H 1.041990 0.250440 0.401719 0.088 Uiso 1 1 d DR U . . .
H4A H 0.384950 0.157849 0.370570 0.088 Uiso 1 1 d DR U . . .
H4B H 0.419640 0.204259 0.434870 0.088 Uiso 1 1 d DR U . . .
H8A H -0.222161 0.738609 0.561780 0.088 Uiso 1 1 d DR U . . .
H8B H -0.018161 0.694579 0.557630 0.088 Uiso 1 1 d DR U . . .
H7A H 1.034779 0.499929 0.333149 0.088 Uiso 1 1 d DR U . . .
H7B H 0.893759 0.535049 0.280689 0.088 Uiso 1 1 d DR 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
Ho1 O1 2.404(5) . ?
Ho1 O2 2.490(4) 2_564 ?
Ho1 N1 2.417(6) . ?
Ho1 N7 2.424(6) 2_564 ?
Ho1 C6 2.920(2) 2_564 ?
Ho1 O4 2.352(2) . ?
Ho1 O5 2.326(2) . ?
Ho1 O6 2.317(2) . ?
Ho1 O7 2.355(2) . ?
O1 C1 1.280(8) . ?
O2 C6 1.271(5) . ?
O3 C3 1.246(9) . ?
N1 C1 1.363(8) . ?
N1 C2 1.332(8) . ?
N2 C2 1.322(10) . ?
N2 C3 1.362(10) . ?
N3 C1 1.343(8) . ?
N3 C4 1.329(8) . ?
N4 C2 1.390(7) . ?
N4 C4 1.409(7) . ?
N4 C5 1.385(8) . ?
N5 C3 1.358(9) . ?
N5 C5 1.329(7) . ?
N6 C4 1.324(9) . ?
N6 C6 1.339(7) . ?
N7 C5 1.314(8) . ?
N7 C6 1.370(5) . ?
O4 H4A 0.8294 . ?
O4 H4B 0.8282 . ?
O5 H5A 0.8269 . ?
O5 H5B 0.8224 . ?
O6 H6A 0.8242 . ?
O6 H6B 0.8210 . ?
O7 H7A 0.8326 . ?
O7 H7B 0.8277 . ?
O8 H8A 0.8255 . ?
O8 H8B 0.8270 . ?

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 Ho1 O2 79.38(15) . 2_564 ?
O1 Ho1 N1 54.06(16) . . ?
O1 Ho1 N7 85.51(17) . 2_564 ?
O1 Ho1 C6 83.53(11) . 2_564 ?
O2 Ho1 C6 25.64(10) 2_564 2_564 ?
N1 Ho1 O2 127.74(17) . 2_564 ?
N1 Ho1 N7 131.67(17) . 2_564 ?
N1 Ho1 C6 137.59(14) . 2_564 ?
N7 Ho1 O2 53.26(16) 2_564 2_564 ?
N7 Ho1 C6 27.78(13) 2_564 2_564 ?
O4 Ho1 O1 87.50(12) . . ?
O4 Ho1 O2 74.23(13) . 2_564 ?
O4 Ho1 N1 80.78(15) . . ?
O4 Ho1 N7 127.44(15) . 2_564 ?
O4 Ho1 C6 99.66(9) . 2_564 ?
O4 Ho1 O7 158.75(11) . . ?
O5 Ho1 O1 126.13(11) . . ?
O5 Ho1 O2 146.24(13) . 2_564 ?
O5 Ho1 N1 72.07(14) . . ?
O5 Ho1 N7 138.64(15) . 2_564 ?
O5 Ho1 C6 150.33(8) . 2_564 ?
O5 Ho1 O4 84.33(7) . . ?
O5 Ho1 O7 79.26(7) . . ?
O6 Ho1 O1 162.20(12) . . ?
O6 Ho1 O2 84.35(12) . 2_564 ?
O6 Ho1 N1 143.74(15) . . ?
O6 Ho1 N7 78.96(15) . 2_564 ?
O6 Ho1 C6 78.68(8) . 2_564 ?
O6 Ho1 O4 95.02(9) . . ?
O6 Ho1 O5 71.68(6) . . ?
O6 Ho1 O7 92.55(8) . . ?
O7 Ho1 O1 91.33(12) . . ?
O7 Ho1 O2 126.36(12) . 2_564 ?
O7 Ho1 N1 81.39(15) . . ?
O7 Ho1 N7 73.53(14) . 2_564 ?
O7 Ho1 C6 101.29(8) . 2_564 ?
C1 O1 Ho1 98.5(4) . . ?
C6 O2 Ho1 96.4(2) . 2_565 ?
C1 N1 Ho1 95.5(4) . . ?
C2 N1 Ho1 146.0(4) . . ?
C2 N1 C1 118.5(5) . . ?
C2 N2 C3 118.4(6) . . ?
C4 N3 C1 116.5(5) . . ?
C2 N4 C4 120.5(5) . . ?
C5 N4 C2 118.8(5) . . ?
C5 N4 C4 120.7(5) . . ?
C5 N5 C3 118.8(5) . . ?
C4 N6 C6 118.4(5) . . ?
C5 N7 Ho1 141.2(4) . 2_565 ?
C5 N7 C6 119.2(5) . . ?
C6 N7 Ho1 96.7(3) . 2_565 ?
O1 C1 N1 112.0(5) . . ?
O1 C1 N3 122.1(6) . . ?
N3 C1 N1 125.9(6) . . ?
N1 C2 N4 118.3(5) . . ?
N2 C2 N1 121.0(6) . . ?
N2 C2 N4 120.8(6) . . ?
O3 C3 N2 118.2(6) . . ?
O3 C3 N5 119.1(6) . . ?
N5 C3 N2 122.6(6) . . ?
N3 C4 N4 120.4(6) . . ?
N6 C4 N3 120.5(6) . . ?
N6 C4 N4 119.1(6) . . ?
N5 C5 N4 120.3(5) . . ?
N7 C5 N4 118.6(5) . . ?
N7 C5 N5 121.1(6) . . ?
O2 C6 Ho1 57.9(2) . 2_565 ?
O2 C6 N6 123.2(4) . . ?
O2 C6 N7 113.0(4) . . ?
N6 C6 Ho1 172.8(4) . 2_565 ?
N6 C6 N7 123.8(4) . . ?
N7 C6 Ho1 55.6(2) . 2_565 ?
Ho1 O4 H4A 124.1 . . ?
Ho1 O4 H4B 121.7 . . ?
H4A O4 H4B 101.1 . . ?
Ho1 O5 H5A 116.1 . . ?
Ho1 O5 H5B 140.3 . . ?
H5A O5 H5B 102.5 . . ?
Ho1 O6 H6A 127.0 . . ?
Ho1 O6 H6B 122.8 . . ?
H6A O6 H6B 102.8 . . ?
Ho1 O7 H7A 123.7 . . ?
Ho1 O7 H7B 113.1 . . ?
H7A O7 H7B 101.8 . . ?
H8A O8 H8B 102.1 . . ?

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
O6 H6A O3 0.82 1.82 2.629(5) 165.1 4_454 yes
O6 H6B O2 0.82 1.99 2.782(5) 163.4 2_664 yes
O5 H5A N2 0.83 1.96 2.741(7) 157.3 . yes
O5 H5B O4 0.82 2.11 2.864 152.0 1_655 yes
O4 H4A O7 0.83 2.01 2.832 171.6 3_445 yes
O4 H4B O8 0.83 1.81 2.595 158.7 3_545 yes
O8 H8A O3 0.83 1.91 2.721(5) 169.6 3_355 yes
O8 H8B N3 0.83 2.62 3.042(6) 113.1 . yes
O8 H8B N6 0.83 2.15 2.932(7) 157.0 . yes
O7 H7A O1 0.83 1.82 2.635(5) 166.8 1_655 yes
O7 H7B N5 0.83 1.90 2.700(6) 163.3 2_564 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
Ho1 O1 C1 N1 1.5(6) . . . . ?
Ho1 O1 C1 N3 -177.8(5) . . . . ?
Ho1 O2 C6 N6 -171.5(4) 2_565 . . . ?
Ho1 O2 C6 N7 7.6(4) 2_565 . . . ?
Ho1 N1 C1 O1 -1.5(5) . . . . ?
Ho1 N1 C1 N3 177.8(6) . . . . ?
Ho1 N1 C2 N2 4.8(12) . . . . ?
Ho1 N1 C2 N4 -175.0(5) . . . . ?
Ho1 N7 C5 N4 -159.5(5) 2_565 . . . ?
Ho1 N7 C5 N5 19.4(10) 2_565 . . . ?
Ho1 N7 C6 O2 -7.8(4) 2_565 . . . ?
Ho1 N7 C6 N6 171.3(4) 2_565 . . . ?
C1 N1 C2 N2 -179.8(6) . . . . ?
C1 N1 C2 N4 0.3(9) . . . . ?
C1 N3 C4 N4 -1.6(9) . . . . ?
C1 N3 C4 N6 178.6(6) . . . . ?
C2 N1 C1 O1 -178.9(6) . . . . ?
C2 N1 C1 N3 0.4(10) . . . . ?
C2 N2 C3 O3 -173.9(6) . . . . ?
C2 N2 C3 N5 5.4(10) . . . . ?
C2 N4 C4 N3 2.4(8) . . . . ?
C2 N4 C4 N6 -177.9(6) . . . . ?
C2 N4 C5 N5 0.7(8) . . . . ?
C2 N4 C5 N7 179.6(5) . . . . ?
C3 N2 C2 N1 177.6(6) . . . . ?
C3 N2 C2 N4 -2.6(10) . . . . ?
C3 N5 C5 N4 1.9(9) . . . . ?
C3 N5 C5 N7 -176.9(6) . . . . ?
C4 N3 C1 O1 179.5(6) . . . . ?
C4 N3 C1 N1 0.3(10) . . . . ?
C4 N4 C2 N1 -1.7(8) . . . . ?
C4 N4 C2 N2 178.5(6) . . . . ?
C4 N4 C5 N5 -178.1(5) . . . . ?
C4 N4 C5 N7 0.7(8) . . . . ?
C4 N6 C6 O2 174.2(5) . . . . ?
C4 N6 C6 N7 -4.8(9) . . . . ?
C5 N4 C2 N1 179.5(6) . . . . ?
C5 N4 C2 N2 -0.3(8) . . . . ?
C5 N4 C4 N3 -178.8(5) . . . . ?
C5 N4 C4 N6 1.0(8) . . . . ?
C5 N5 C3 O3 174.2(6) . . . . ?
C5 N5 C3 N2 -5.1(10) . . . . ?
C5 N7 C6 Ho1 -164.7(7) . . . 2_565 ?
C5 N7 C6 O2 -172.5(5) . . . . ?
C5 N7 C6 N6 6.6(8) . . . . ?
C6 N6 C4 N3 -179.3(6) . . . . ?
C6 N6 C4 N4 1.0(9) . . . . ?
C6 N7 C5 N4 -4.3(8) . . . . ?
C6 N7 C5 N5 174.6(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.610(13)
2 0.390(13)

####################################################################### 
# 
# 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_ada283
_database_code_depnum_ccdc_archive 'CCDC 2178361'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2022-06-10 deposited with the CCDC.	2022-09-01 downloaded from the CCDC.
;
_audit_creation_date             2020-07-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H14 N7 O10 Sm'
_chemical_formula_sum            'C6 H14 N7 O10 Sm'
_chemical_formula_weight         494.59
_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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sm Sm -5.3236 12.2178 '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                   11.9028(6)
_cell_length_b                   6.8680(3)
_cell_length_c                   16.7913(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.617(2)
_cell_angle_gamma                90
_cell_volume                     1369.93(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    298
_cell_measurement_theta_max      70.067
_cell_measurement_theta_min      4.425
_shelx_estimated_absorpt_T_max   0.353
_shelx_estimated_absorpt_T_min   0.024
_exptl_absorpt_coefficient_mu    32.936
_exptl_absorpt_correction_T_max  0.2238
_exptl_absorpt_correction_T_min  0.0555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1592 before and 0.0522 after correction.
The Ratio of minimum to maximum transmission is 0.2480.
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    2.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             964
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_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  0.0372
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_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            35375
_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         70.092
_diffrn_reflns_theta_min         4.424
_diffrn_ambient_temperature      298
_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 1.000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2597
_reflns_number_total             2614
_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 (2017) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2017) V8.38A; 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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.953
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         2614
_refine_ls_number_restraints     105
_refine_ls_R_factor_all          0.0207
_refine_ls_R_factor_gt           0.0206
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²+0.6711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0571
_refine_ls_wR_factor_ref         0.0571
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O4-H4A = O4-H4B = O5-H5A = O5-H5B = O6-H6A = O6-H6B = O7-H7A = O7-H7B = O8-
 H8A = O8-H8B = O9-H9A = O9-H9B = O10-H10A = O10-H10B
 0.87 with sigma of 0.002
 O4-H4A \\sim O4-H4B \\sim O5-H5A \\sim O5-H5B \\sim O6-H6A \\sim O6-H6B \\sim
O7-H7A \\sim O7-H7B \\sim O8-
 H8A \\sim O8-H8B \\sim O9-H9A \\sim O9-H9B \\sim O10-H10A \\sim O10-H10B
 with sigma of 0.002
;
_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
Sm1 Sm 0.48114(2) 0.63765(2) 0.82335(2) 0.02094(8) Uani 1 1 d . . . . .
O1 O 0.33345(16) 0.7666(4) 0.72746(11) 0.0351(5) Uani 1 1 d . . . . .
O2 O 0.82040(16) 0.5932(3) 0.55085(13) 0.0313(4) Uani 1 1 d . . . . .
O3 O 0.35138(19) 0.8570(3) 0.32438(13) 0.0334(5) Uani 1 1 d . . . . .
O4 O 0.3977(2) 0.3454(3) 0.75360(14) 0.0363(5) Uani 1 1 d D . . . .
H4A H 0.3261(8) 0.318(6) 0.751(3) 0.054 Uiso 1 1 d D U . . .
H4B H 0.419(3) 0.309(6) 0.7072(11) 0.054 Uiso 1 1 d D U . . .
O5 O 0.31757(17) 0.5868(3) 0.89341(13) 0.0342(4) Uani 1 1 d D . . . .
H5A H 0.279(3) 0.479(3) 0.895(2) 0.051 Uiso 1 1 d D U . . .
H5B H 0.269(2) 0.668(4) 0.911(2) 0.051 Uiso 1 1 d D U . . .
O6 O 0.50110(19) 0.3491(3) 0.91508(14) 0.0327(5) Uani 1 1 d D . . . .
H6A H 0.5648(17) 0.292(5) 0.928(2) 0.049 Uiso 1 1 d D U . . .
H6B H 0.469(3) 0.338(6) 0.9602(12) 0.049 Uiso 1 1 d D U . . .
O7 O 0.4121(2) 0.9421(3) 0.89067(15) 0.0445(5) Uani 1 1 d D . . . .
H7A H 0.423(4) 1.057(3) 0.871(2) 0.067 Uiso 1 1 d D U . . .
H7B H 0.373(3) 0.941(8) 0.9327(14) 0.067 Uiso 1 1 d D U . . .
O8 O 0.60848(15) 0.7128(3) 0.94457(11) 0.0288(4) Uani 1 1 d D . . . .
H8A H 0.6752(13) 0.661(5) 0.949(3) 0.043 Uiso 1 1 d D U . . .
H8B H 0.619(4) 0.8378(11) 0.948(3) 0.043 Uiso 1 1 d D U . . .
O9 O 0.64941(16) 0.4590(3) 0.79694(12) 0.0340(4) Uani 1 1 d D . . . .
H9A H 0.658(4) 0.389(4) 0.7546(13) 0.051 Uiso 1 1 d D U . . .
H9B H 0.7144(15) 0.515(5) 0.806(2) 0.051 Uiso 1 1 d D U . . .
O10 O 0.6000(2) 0.9209(4) 0.79987(12) 0.0393(5) Uani 1 1 d D . . . .
H10A H 0.604(4) 0.977(6) 0.7536(11) 0.059 Uiso 1 1 d D U . . .
H10B H 0.632(3) 0.999(5) 0.8351(18) 0.059 Uiso 1 1 d D U . . .
N1 N 0.4924(2) 0.6934(4) 0.67203(13) 0.0263(4) Uani 1 1 d . . . . .
N2 N 0.6600(2) 0.6321(3) 0.61394(16) 0.0280(5) Uani 1 1 d . . . . .
N3 N 0.32793(17) 0.7947(4) 0.59249(13) 0.0262(4) Uani 1 1 d . . . . .
N4 N 0.50002(16) 0.7357(3) 0.53432(12) 0.0221(4) Uani 1 1 d . . . . .
N5 N 0.66936(19) 0.6823(4) 0.47249(14) 0.0262(4) Uani 1 1 d . . . . .
N6 N 0.33858(19) 0.8379(3) 0.45762(14) 0.0258(5) Uani 1 1 d . . . . .
N7 N 0.51179(18) 0.7762(3) 0.39532(12) 0.0264(4) Uani 1 1 d . . . . .
C1 C 0.3831(2) 0.7523(4) 0.66354(15) 0.0253(5) Uani 1 1 d . . . . .
C2 C 0.5531(2) 0.6853(4) 0.60855(15) 0.0226(5) Uani 1 1 d . . . . .
C3 C 0.7165(2) 0.6358(3) 0.54615(19) 0.0256(6) Uani 1 1 d . . . . .
C4 C 0.3863(2) 0.7904(4) 0.52797(15) 0.0220(5) Uani 1 1 d . . . . .
C5 C 0.5616(2) 0.7321(4) 0.46574(14) 0.0223(5) Uani 1 1 d . . . . .
C6 C 0.4004(2) 0.8245(4) 0.39183(16) 0.0251(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
Sm1 O1 2.4719(19) . ?
Sm1 O4 2.498(2) . ?
Sm1 O5 2.363(2) . ?
Sm1 O6 2.512(2) . ?
Sm1 O7 2.538(2) . ?
Sm1 O8 2.5134(18) . ?
Sm1 O9 2.414(2) . ?
Sm1 O10 2.452(2) . ?
Sm1 N1 2.581(2) . ?
Sm1 C1 2.964(3) . ?
O1 C1 1.261(3) . ?
O2 C3 1.268(3) . ?
O3 C6 1.261(4) . ?
O4 H4A 0.8698(14) . ?
O4 H4B 0.8699(13) . ?
O5 H5A 0.8699(13) . ?
O5 H5B 0.8700(13) . ?
O6 H6A 0.8699(13) . ?
O6 H6B 0.8699(13) . ?
O7 H7A 0.8699(13) . ?
O7 H7B 0.8698(13) . ?
O8 H8A 0.8699(13) . ?
O8 H8B 0.8698(14) . ?
O9 H9A 0.8698(13) . ?
O9 H9B 0.8699(14) . ?
O10 H10A 0.8699(13) . ?
O10 H10B 0.8699(13) . ?
N1 C1 1.362(3) . ?
N1 C2 1.326(3) . ?
N2 C2 1.322(4) . ?
N2 C3 1.358(4) . ?
N3 C1 1.357(3) . ?
N3 C4 1.324(3) . ?
N4 C2 1.405(3) . ?
N4 C4 1.402(3) . ?
N4 C5 1.403(3) . ?
N5 C3 1.364(4) . ?
N5 C5 1.326(3) . ?
N6 C4 1.319(3) . ?
N6 C6 1.368(4) . ?
N7 C5 1.324(3) . ?
N7 C6 1.364(4) . ?

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 Sm1 O4 74.76(8) . . ?
O1 Sm1 O6 135.89(8) . . ?
O1 Sm1 O7 75.99(8) . . ?
O1 Sm1 O8 145.25(7) . . ?
O1 Sm1 N1 52.04(7) . . ?
O1 Sm1 C1 24.77(7) . . ?
O4 Sm1 O6 70.91(8) . . ?
O4 Sm1 O7 137.76(8) . . ?
O4 Sm1 O8 138.27(7) . . ?
O4 Sm1 N1 72.64(8) . . ?
O4 Sm1 C1 70.54(8) . . ?
O5 Sm1 O1 78.63(7) . . ?
O5 Sm1 O4 78.40(8) . . ?
O5 Sm1 O6 68.11(8) . . ?
O5 Sm1 O7 66.42(7) . . ?
O5 Sm1 O8 95.79(7) . . ?
O5 Sm1 O9 137.35(8) . . ?
O5 Sm1 O10 134.36(8) . . ?
O5 Sm1 N1 127.42(8) . . ?
O5 Sm1 C1 101.55(8) . . ?
O6 Sm1 O7 113.43(8) . . ?
O6 Sm1 O8 68.69(7) . . ?
O6 Sm1 N1 135.38(8) . . ?
O6 Sm1 C1 141.37(8) . . ?
O7 Sm1 N1 110.77(8) . . ?
O7 Sm1 C1 93.69(8) . . ?
O8 Sm1 O7 70.48(8) . . ?
O8 Sm1 N1 134.46(7) . . ?
O8 Sm1 C1 149.47(7) . . ?
O9 Sm1 O1 128.81(7) . . ?
O9 Sm1 O4 79.37(7) . . ?
O9 Sm1 O6 70.37(7) . . ?
O9 Sm1 O7 142.78(8) . . ?
O9 Sm1 O8 77.77(7) . . ?
O9 Sm1 O10 83.09(8) . . ?
O9 Sm1 N1 78.42(7) . . ?
O9 Sm1 C1 104.63(7) . . ?
O10 Sm1 O1 90.28(8) . . ?
O10 Sm1 O4 141.12(8) . . ?
O10 Sm1 O6 133.73(8) . . ?
O10 Sm1 O7 67.94(8) . . ?
O10 Sm1 O8 69.06(7) . . ?
O10 Sm1 N1 69.97(8) . . ?
O10 Sm1 C1 80.91(7) . . ?
N1 Sm1 C1 27.33(7) . . ?
C1 O1 Sm1 100.02(15) . . ?
Sm1 O4 H4A 124(3) . . ?
Sm1 O4 H4B 121(3) . . ?
H4A O4 H4B 103(4) . . ?
Sm1 O5 H5A 126(3) . . ?
Sm1 O5 H5B 132(3) . . ?
H5A O5 H5B 100(3) . . ?
Sm1 O6 H6A 124(3) . . ?
Sm1 O6 H6B 125(3) . . ?
H6A O6 H6B 99(4) . . ?
Sm1 O7 H7A 121(3) . . ?
Sm1 O7 H7B 124(4) . . ?
H7A O7 H7B 115(5) . . ?
Sm1 O8 H8A 119(3) . . ?
Sm1 O8 H8B 110(3) . . ?
H8A O8 H8B 106(4) . . ?
Sm1 O9 H9A 125(3) . . ?
Sm1 O9 H9B 119(3) . . ?
H9A O9 H9B 104(4) . . ?
Sm1 O10 H10A 124(3) . . ?
Sm1 O10 H10B 128(3) . . ?
H10A O10 H10B 107(4) . . ?
C1 N1 Sm1 92.19(15) . . ?
C2 N1 Sm1 148.21(18) . . ?
C2 N1 C1 119.6(2) . . ?
C2 N2 C3 117.6(2) . . ?
C4 N3 C1 117.7(2) . . ?
C4 N4 C2 120.8(2) . . ?
C4 N4 C5 119.6(2) . . ?
C5 N4 C2 119.7(2) . . ?
C5 N5 C3 118.6(2) . . ?
C4 N6 C6 118.9(2) . . ?
C5 N7 C6 118.2(2) . . ?
O1 C1 Sm1 55.20(13) . . ?
O1 C1 N1 115.5(2) . . ?
O1 C1 N3 120.3(2) . . ?
N1 C1 Sm1 60.49(13) . . ?
N3 C1 Sm1 173.81(19) . . ?
N3 C1 N1 124.2(2) . . ?
N1 C2 N4 117.8(2) . . ?
N2 C2 N1 121.8(2) . . ?
N2 C2 N4 120.4(2) . . ?
O2 C3 N2 118.4(3) . . ?
O2 C3 N5 117.0(3) . . ?
N2 C3 N5 124.6(3) . . ?
N3 C4 N4 119.9(2) . . ?
N6 C4 N3 120.6(2) . . ?
N6 C4 N4 119.6(2) . . ?
N5 C5 N4 119.1(2) . . ?
N7 C5 N4 120.1(2) . . ?
N7 C5 N5 120.8(2) . . ?
O3 C6 N6 118.1(3) . . ?
O3 C6 N7 118.4(3) . . ?
N7 C6 N6 123.5(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 O1 0.8698(14) 1.987(11) 2.841(3) 167(4) 2_546 yes
O4 H4B N7 0.8699(13) 2.042(6) 2.907(3) 173(4) 3_666 yes
O5 H5A N3 0.8699(13) 1.819(10) 2.670(3) 166(4) 2_546 yes
O5 H5B N5 0.8700(13) 1.918(10) 2.772(3) 167(4) 4_576 yes
O6 H6A O2 0.8699(13) 1.947(13) 2.788(3) 162(4) 2_646 yes
O6 H6B O8 0.8699(13) 1.931(5) 2.797(3) 174(4) 3_667 yes
O7 H7A O6 0.8699(13) 2.31(3) 3.008(3) 137(4) 1_565 yes
O7 H7B O2 0.8698(13) 2.131(12) 2.976(3) 164(4) 4_576 yes
O8 H8A N6 0.8699(13) 1.940(15) 2.756(3) 156(3) 4_676 yes
O8 H8B O2 0.8698(14) 1.895(12) 2.746(3) 166(4) 2_656 yes
O9 H9A O3 0.8698(13) 2.145(14) 2.976(3) 160(4) 3_666 yes
O9 H9B O3 0.8699(14) 1.860(3) 2.729(3) 178(4) 4_676 yes
O10 H10A O3 0.8699(13) 1.842(15) 2.677(3) 160(4) 3_676 yes
O10 H10B O2 0.8699(13) 2.066(17) 2.878(3) 155(4) 2_656 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
Sm1 O1 C1 N1 -5.3(3) . . . . ?
Sm1 O1 C1 N3 174.9(2) . . . . ?
Sm1 N1 C1 O1 5.0(3) . . . . ?
Sm1 N1 C1 N3 -175.2(2) . . . . ?
Sm1 N1 C2 N2 -3.0(5) . . . . ?
Sm1 N1 C2 N4 177.0(3) . . . . ?
C1 N1 C2 N2 178.9(3) . . . . ?
C1 N1 C2 N4 -1.0(4) . . . . ?
C1 N3 C4 N4 2.5(4) . . . . ?
C1 N3 C4 N6 -177.3(2) . . . . ?
C2 N1 C1 Sm1 179.0(3) . . . . ?
C2 N1 C1 O1 -176.1(3) . . . . ?
C2 N1 C1 N3 3.7(4) . . . . ?
C2 N2 C3 O2 177.0(2) . . . . ?
C2 N2 C3 N5 -3.0(4) . . . . ?
C2 N4 C4 N3 -0.1(4) . . . . ?
C2 N4 C4 N6 179.7(2) . . . . ?
C2 N4 C5 N5 -0.5(4) . . . . ?
C2 N4 C5 N7 178.9(2) . . . . ?
C3 N2 C2 N1 -177.4(2) . . . . ?
C3 N2 C2 N4 2.5(4) . . . . ?
C3 N5 C5 N4 0.1(4) . . . . ?
C3 N5 C5 N7 -179.2(2) . . . . ?
C4 N3 C1 O1 175.3(3) . . . . ?
C4 N3 C1 N1 -4.4(4) . . . . ?
C4 N4 C2 N1 -0.7(4) . . . . ?
C4 N4 C2 N2 179.4(2) . . . . ?
C4 N4 C5 N5 179.2(2) . . . . ?
C4 N4 C5 N7 -1.4(4) . . . . ?
C4 N6 C6 O3 175.0(2) . . . . ?
C4 N6 C6 N7 -4.3(4) . . . . ?
C5 N4 C2 N1 179.0(2) . . . . ?
C5 N4 C2 N2 -0.9(4) . . . . ?
C5 N4 C4 N3 -179.8(2) . . . . ?
C5 N4 C4 N6 0.0(4) . . . . ?
C5 N5 C3 O2 -178.4(2) . . . . ?
C5 N5 C3 N2 1.6(4) . . . . ?
C5 N7 C6 O3 -176.4(2) . . . . ?
C5 N7 C6 N6 2.9(4) . . . . ?
C6 N6 C4 N3 -177.5(2) . . . . ?
C6 N6 C4 N4 2.7(4) . . . . ?
C6 N7 C5 N4 0.0(4) . . . . ?
C6 N7 C5 N5 179.4(2) . . . . ?

_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_cecy
_database_code_depnum_ccdc_archive 'CCDC 2178358'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2022-06-10 deposited with the CCDC.	2022-09-01 downloaded from the CCDC.
;
_audit_creation_date             2022-03-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H12 Ce N7 O9, H2 O'
_chemical_formula_sum            'C6 H14 Ce N7 O10'
_chemical_formula_weight         484.36
_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 0.0139 0.0070 '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'
Ce Ce -0.6940 7.7240 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0240 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0250 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.6711(4)
_cell_length_b                   19.7592(12)
_cell_length_c                   21.1063(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.303(2)
_cell_angle_gamma                90
_cell_volume                     2753.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9132
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.705
_cell_measurement_theta_min      3.683
_shelx_estimated_absorpt_T_max   0.613
_shelx_estimated_absorpt_T_min   0.293
_exptl_absorpt_coefficient_mu    18.091
_exptl_absorpt_correction_T_max  0.1551
_exptl_absorpt_correction_T_min  0.0440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1337 before and 0.0505 after correction. The Ratio of minimum to maximum transmission is 0.2837. 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    2.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1896
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_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 Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            79204
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.720
_diffrn_reflns_theta_min         2.678
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6176
_reflns_number_total             6336
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       0.00034(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     518
_refine_ls_number_reflns         6336
_refine_ls_number_restraints     332
_refine_ls_R_factor_all          0.0182
_refine_ls_R_factor_gt           0.0175
_refine_ls_restrained_S_all      1.081
_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)+(0.0270P)²+1.7755P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0454
_refine_ls_wR_factor_ref         0.0458
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 H13A-H18A_$1
 2.2 with sigma of 0.02
 O7-H7A \\sim O7-H7B \\sim O8-H8A \\sim O8-H8B \\sim O9-H9A \\sim O9-H9B \\sim
O10-H10A \\sim O10-H10B ~
 O11-H11A \\sim O11-H11B \\sim O12-H12A \\sim O12-H12B \\sim O13-H13A \\sim
O13-H13B \\sim O14-H14A ~
 O14-H14B \\sim O15-H15A \\sim O15-H15B \\sim O16-H16A \\sim O16-H16B \\sim
O17-H17A \\sim O17-H17B ~
 O18-H18A \\sim O18-H18B
 with sigma of 0.02
 H7A-H7B \\sim H8A-H8B \\sim H9A-H9B \\sim H10A-H10B \\sim H11A-H11B \\sim
H12A-H12B \\sim H13A-H13B ~
 H14A-H14B \\sim H16A-H16B \\sim H17A-H17B \\sim H18A-H18B
 with sigma of 0.02
;
_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
Ce1 Ce 0.63872(2) 0.61718(2) 0.59545(2) 0.01747(4) Uani 1 1 d . . . . .
Ce2 Ce 0.66397(2) 0.05297(2) 0.63220(2) 0.01831(4) Uani 1 1 d . . . . .
O1 O 0.5591(2) 0.50592(7) 0.62851(7) 0.0238(3) Uani 1 1 d . . . . .
O2 O 0.9284(2) 0.30614(8) 0.88178(7) 0.0258(3) Uani 1 1 d . . . . .
O3 O 0.5034(3) 0.16349(7) 0.60182(7) 0.0298(3) Uani 1 1 d . . . . .
O4 O 0.5569(2) -0.06478(7) 0.58083(7) 0.0229(3) Uani 1 1 d . . . . .
O5 O 0.9842(2) -0.08346(7) 0.89157(7) 0.0224(3) Uani 1 1 d . . . . .
O6 O 0.7954(2) -0.37172(7) 0.71495(7) 0.0218(3) Uani 1 1 d . . . . .
O7 O 0.9629(2) 0.55160(7) 0.60952(8) 0.0247(3) Uani 1 1 d D . . . .
H7A H 0.985(4) 0.5125(7) 0.6095(15) 0.037 Uiso 1 1 d D U . . .
H7B H 1.063(3) 0.5705(12) 0.6054(15) 0.037 Uiso 1 1 d D U . . .
O8 O 0.9312(2) 0.68593(8) 0.57054(8) 0.0263(3) Uani 1 1 d D . . . .
H8A H 0.970(5) 0.7175(11) 0.5910(11) 0.039 Uiso 1 1 d D U . . .
H8B H 0.948(5) 0.6931(14) 0.5349(7) 0.039 Uiso 1 1 d D U . . .
O9 O 0.3412(2) 0.63040(8) 0.65728(7) 0.0231(3) Uani 1 1 d D . . . .
H9A H 0.329(5) 0.6090(11) 0.6885(10) 0.035 Uiso 1 1 d D U . . .
H9B H 0.313(5) 0.6678(8) 0.6657(13) 0.035 Uiso 1 1 d D U . . .
O10 O 0.4840(2) 0.71818(8) 0.52732(7) 0.0265(3) Uani 1 1 d D . . . .
H10A H 0.502(5) 0.7554(9) 0.5427(12) 0.040 Uiso 1 1 d D U . . .
H10B H 0.506(5) 0.7226(14) 0.4912(8) 0.040 Uiso 1 1 d D U . . .
O11 O 0.7201(2) 0.57697(8) 0.48756(7) 0.0246(3) Uani 1 1 d D . . . .
H11A H 0.824(2) 0.5818(16) 0.4745(13) 0.037 Uiso 1 1 d D U . . .
H11B H 0.637(3) 0.5865(15) 0.4578(11) 0.037 Uiso 1 1 d D U . . .
O12 O 0.3166(2) 0.57213(8) 0.51934(7) 0.0267(3) Uani 1 1 d D . . . .
H12A H 0.280(5) 0.5855(13) 0.4848(9) 0.040 Uiso 1 1 d D U . . .
H12B H 0.303(5) 0.5321(7) 0.5191(13) 0.040 Uiso 1 1 d D U . . .
O13 O 0.3177(2) 0.04829(8) 0.55770(7) 0.0246(3) Uani 1 1 d D . . . .
H13A H 0.288(4) 0.0193(9) 0.5333(12) 0.037 Uiso 1 1 d D U . . .
H13B H 0.268(4) 0.0822(8) 0.5422(13) 0.037 Uiso 1 1 d D U . . .
O14 O 0.3961(2) 0.04826(8) 0.70268(8) 0.0253(3) Uani 1 1 d D . . . .
H14A H 0.375(5) 0.0171(9) 0.7244(12) 0.038 Uiso 1 1 d D U . . .
H14B H 0.351(4) 0.0801(9) 0.7185(13) 0.038 Uiso 1 1 d D U . . .
O15 O 0.8454(2) 0.05843(7) 0.74591(7) 0.0245(3) Uani 1 1 d D . . . .
H15A H 0.950(3) 0.0768(14) 0.7571(14) 0.037 Uiso 1 1 d D U . . .
H15B H 0.860(5) 0.0217(9) 0.7608(14) 0.037 Uiso 1 1 d D U . . .
O16 O 0.9943(2) -0.01264(9) 0.62111(8) 0.0291(3) Uani 1 1 d D . . . .
H16A H 1.040(4) -0.0403(13) 0.6458(13) 0.044 Uiso 1 1 d D U . . .
H16B H 1.086(4) 0.0066(14) 0.6094(14) 0.044 Uiso 1 1 d D U . . .
O17 O 0.9570(3) 0.13352(9) 0.63108(8) 0.0338(4) Uani 1 1 d D . . . .
H17A H 1.001(5) 0.1618(13) 0.6568(13) 0.051 Uiso 1 1 d D U . . .
H17B H 1.058(3) 0.1209(16) 0.6182(16) 0.051 Uiso 1 1 d D U . . .
O18 O 0.7316(2) 0.06941(8) 0.51880(7) 0.0239(3) Uani 1 1 d D . . . .
H18A H 0.644(3) 0.0841(10) 0.4918(11) 0.036 Uiso 1 1 d D U . . .
H18B H 0.829(3) 0.0911(14) 0.5125(14) 0.036 Uiso 1 1 d D U . . .
N1 N 0.6762(3) 0.44433(8) 0.71650(8) 0.0204(3) Uani 1 1 d . . . . .
N2 N 0.8018(3) 0.37681(8) 0.80186(8) 0.0209(3) Uani 1 1 d . . . . .
N3 N 0.5444(3) 0.39318(9) 0.61564(8) 0.0213(3) Uani 1 1 d . . . . .
N4 N 0.6517(3) 0.32542(8) 0.70575(8) 0.0194(3) Uani 1 1 d . . . . .
N5 N 0.7639(3) 0.25507(9) 0.79410(8) 0.0214(3) Uani 1 1 d . . . . .
N6 N 0.5226(3) 0.27723(9) 0.60588(8) 0.0235(3) Uani 1 1 d . . . . .
N7 N 0.6256(3) 0.20635(9) 0.69852(9) 0.0241(3) Uani 1 1 d . . . . .
N8 N 0.6792(3) -0.06937(8) 0.68398(8) 0.0197(3) Uani 1 1 d . . . . .
N9 N 0.6049(3) -0.17127(8) 0.62205(8) 0.0198(3) Uani 1 1 d . . . . .
N10 N 0.8275(3) -0.07364(8) 0.78931(8) 0.0203(3) Uani 1 1 d . . . . .
N11 N 0.7598(2) -0.17509(8) 0.73059(7) 0.0177(3) Uani 1 1 d . . . . .
N12 N 0.6931(3) -0.27366(8) 0.66974(8) 0.0198(3) Uani 1 1 d . . . . .
N13 N 0.9181(3) -0.18166(9) 0.83788(8) 0.0207(3) Uani 1 1 d . . . . .
N14 N 0.8538(3) -0.27981(8) 0.77951(8) 0.0205(3) Uani 1 1 d . . . . .
C1 C 0.5935(3) 0.44854(10) 0.65355(10) 0.0201(4) Uani 1 1 d . . . . .
C2 C 0.7109(3) 0.38315(10) 0.74224(10) 0.0193(4) Uani 1 1 d . . . . .
C3 C 0.5711(3) 0.33167(10) 0.64102(9) 0.0195(4) Uani 1 1 d . . . . .
C4 C 0.8311(3) 0.31269(10) 0.82683(9) 0.0207(4) Uani 1 1 d . . . . .
C5 C 0.6811(3) 0.26063(10) 0.73312(10) 0.0202(4) Uani 1 1 d . . . . .
C6 C 0.5495(3) 0.21511(10) 0.63524(10) 0.0235(4) Uani 1 1 d . . . . .
C7 C 0.6121(3) -0.10269(10) 0.62807(9) 0.0197(4) Uani 1 1 d . . . . .
C8 C 0.7560(3) -0.10439(10) 0.73527(9) 0.0190(4) Uani 1 1 d . . . . .
C9 C 0.9104(3) -0.11193(10) 0.84084(9) 0.0193(4) Uani 1 1 d . . . . .
C10 C 0.6833(3) -0.20658(10) 0.67253(9) 0.0189(4) Uani 1 1 d . . . . .
C11 C 0.8453(3) -0.21278(10) 0.78413(9) 0.0191(4) Uani 1 1 d . . . . .
C12 C 0.7823(3) -0.30824(10) 0.72218(9) 0.0193(4) Uani 1 1 d . . . . .
O19 O 1.0599(3) 0.14148(9) 0.49681(9) 0.0319(4) Uani 1 1 d . . . . .
H19A H 1.040(5) 0.1444(18) 0.4602(18) 0.048 Uiso 1 1 d . U . . .
H19B H 1.053(5) 0.1789(18) 0.5138(17) 0.048 Uiso 1 1 d . U . . .
O20 O 0.9497(3) 0.26647(10) 0.54034(9) 0.0346(4) Uani 1 1 d . . . . .
H20A H 0.838(6) 0.2707(18) 0.5318(18) 0.052 Uiso 1 1 d . U . . .
H20B H 0.987(5) 0.2823(18) 0.5778(19) 0.052 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ce1 O1 2.3892(14) . ?
Ce1 O6 2.5964(14) 1_565 ?
Ce1 O7 2.5017(15) . ?
Ce1 O8 2.4953(15) . ?
Ce1 O9 2.5415(15) . ?
Ce1 O10 2.5860(15) . ?
Ce1 O11 2.5434(15) . ?
Ce1 O12 2.6445(16) . ?
Ce1 N12 2.6605(17) 1_565 ?
Ce1 C12 3.083(2) 1_565 ?
Ce2 O3 2.4757(15) . ?
Ce2 O4 2.6221(15) . ?
Ce2 O13 2.6018(15) . ?
Ce2 O14 2.4867(15) . ?
Ce2 O15 2.5293(15) . ?
Ce2 O16 2.5960(16) . ?
Ce2 O17 2.5236(16) . ?
Ce2 O18 2.5199(15) . ?
Ce2 N8 2.6487(17) . ?
O1 C1 1.258(2) . ?
O2 C4 1.251(2) . ?
O3 C6 1.253(3) . ?
O4 C7 1.259(2) . ?
O5 C9 1.246(2) . ?
O6 C12 1.268(2) . ?
O7 H7A 0.787(14) . ?
O7 H7B 0.782(14) . ?
O8 H8A 0.781(14) . ?
O8 H8B 0.790(14) . ?
O9 H9A 0.797(14) . ?
O9 H9B 0.789(14) . ?
O10 H10A 0.807(14) . ?
O10 H10B 0.802(14) . ?
O11 H11A 0.790(14) . ?
O11 H11B 0.799(14) . ?
O12 H12A 0.781(14) . ?
O12 H12B 0.797(14) . ?
O13 H13A 0.776(14) . ?
O13 H13B 0.796(14) . ?
O14 H14A 0.793(14) . ?
O14 H14B 0.791(14) . ?
O15 H15A 0.791(15) . ?
O15 H15B 0.791(15) . ?
O16 H16A 0.785(14) . ?
O16 H16B 0.788(15) . ?
O17 H17A 0.806(15) . ?
O17 H17B 0.802(15) . ?
O18 H18A 0.809(14) . ?
O18 H18B 0.805(14) . ?
N1 C1 1.366(3) . ?
N1 C2 1.332(3) . ?
N2 C2 1.322(3) . ?
N2 C4 1.375(3) . ?
N3 C1 1.367(3) . ?
N3 C3 1.330(3) . ?
N4 C2 1.401(2) . ?
N4 C3 1.399(2) . ?
N4 C5 1.407(2) . ?
N5 C4 1.373(3) . ?
N5 C5 1.330(3) . ?
N6 C3 1.320(3) . ?
N6 C6 1.375(3) . ?
N7 C5 1.320(3) . ?
N7 C6 1.370(3) . ?
N8 C7 1.369(3) . ?
N8 C8 1.324(3) . ?
N9 C7 1.361(3) . ?
N9 C10 1.317(3) . ?
N10 C8 1.319(3) . ?
N10 C9 1.374(3) . ?
N11 C8 1.401(2) . ?
N11 C10 1.403(2) . ?
N11 C11 1.404(2) . ?
N12 C10 1.329(3) . ?
N12 C12 1.362(2) . ?
N13 C9 1.381(2) . ?
N13 C11 1.320(3) . ?
N14 C11 1.330(3) . ?
N14 C12 1.357(3) . ?
O19 H19A 0.77(4) . ?
O19 H19B 0.83(4) . ?
O20 H20A 0.75(4) . ?
O20 H20B 0.85(4) . ?

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 Ce1 O6 82.48(5) . 1_565 ?
O1 Ce1 O7 73.35(5) . . ?
O1 Ce1 O8 140.89(5) . . ?
O1 Ce1 O9 73.84(5) . . ?
O1 Ce1 O10 141.71(5) . . ?
O1 Ce1 O11 93.40(5) . . ?
O1 Ce1 O12 70.88(5) . . ?
O1 Ce1 N12 126.22(5) . 1_565 ?
O1 Ce1 C12 103.93(5) . 1_565 ?
O6 Ce1 O12 142.78(5) 1_565 . ?
O6 Ce1 N12 50.02(5) 1_565 1_565 ?
O6 Ce1 C12 23.89(5) 1_565 1_565 ?
O7 Ce1 O6 73.06(5) . 1_565 ?
O7 Ce1 O9 135.90(5) . . ?
O7 Ce1 O10 137.26(5) . . ?
O7 Ce1 O11 69.62(5) . . ?
O7 Ce1 O12 120.69(5) . . ?
O7 Ce1 N12 107.94(5) . 1_565 ?
O7 Ce1 C12 89.40(5) . 1_565 ?
O8 Ce1 O6 86.64(5) . 1_565 ?
O8 Ce1 O7 67.55(5) . . ?
O8 Ce1 O9 138.14(5) . . ?
O8 Ce1 O10 73.98(5) . . ?
O8 Ce1 O11 72.95(5) . . ?
O8 Ce1 O12 130.30(5) . . ?
O8 Ce1 N12 68.81(5) . 1_565 ?
O8 Ce1 C12 76.59(5) . 1_565 ?
O9 Ce1 O6 74.16(5) . 1_565 ?
O9 Ce1 O10 85.85(5) . . ?
O9 Ce1 O11 140.85(5) . . ?
O9 Ce1 O12 73.75(5) . . ?
O9 Ce1 N12 70.38(5) . 1_565 ?
O9 Ce1 C12 70.93(5) . 1_565 ?
O10 Ce1 O6 123.18(5) . 1_565 ?
O10 Ce1 O12 72.42(5) . . ?
O10 Ce1 N12 73.23(5) . 1_565 ?
O10 Ce1 C12 99.36(5) . 1_565 ?
O11 Ce1 O6 142.01(5) . 1_565 ?
O11 Ce1 O10 82.12(5) . . ?
O11 Ce1 O12 67.10(5) . . ?
O11 Ce1 N12 138.79(5) . 1_565 ?
O11 Ce1 C12 147.82(5) . 1_565 ?
O12 Ce1 N12 131.34(5) . 1_565 ?
O12 Ce1 C12 144.23(5) . 1_565 ?
N12 Ce1 C12 26.14(5) 1_565 1_565 ?
O3 Ce2 O4 126.43(5) . . ?
O3 Ce2 O13 64.00(5) . . ?
O3 Ce2 O14 82.33(5) . . ?
O3 Ce2 O15 109.75(5) . . ?
O3 Ce2 O16 139.31(6) . . ?
O3 Ce2 O17 75.40(6) . . ?
O3 Ce2 O18 76.73(5) . . ?
O3 Ce2 N8 154.33(6) . . ?
O4 Ce2 N8 49.66(5) . . ?
O13 Ce2 O4 63.48(5) . . ?
O13 Ce2 N8 101.23(5) . . ?
O14 Ce2 O4 92.16(5) . . ?
O14 Ce2 O13 73.02(5) . . ?
O14 Ce2 O15 73.78(5) . . ?
O14 Ce2 O16 136.71(5) . . ?
O14 Ce2 O17 130.83(5) . . ?
O14 Ce2 O18 144.67(5) . . ?
O14 Ce2 N8 72.97(5) . . ?
O15 Ce2 O4 119.65(5) . . ?
O15 Ce2 O13 146.76(5) . . ?
O15 Ce2 O16 79.10(5) . . ?
O15 Ce2 N8 70.30(5) . . ?
O16 Ce2 O4 72.77(5) . . ?
O16 Ce2 O13 128.24(5) . . ?
O16 Ce2 N8 66.35(5) . . ?
O17 Ce2 O4 136.13(5) . . ?
O17 Ce2 O13 129.66(6) . . ?
O17 Ce2 O15 73.55(5) . . ?
O17 Ce2 O16 69.23(6) . . ?
O17 Ce2 N8 126.57(6) . . ?
O18 Ce2 O4 78.30(5) . . ?
O18 Ce2 O13 72.29(5) . . ?
O18 Ce2 O15 140.26(5) . . ?
O18 Ce2 O16 73.02(5) . . ?
O18 Ce2 O17 70.40(5) . . ?
O18 Ce2 N8 120.53(5) . . ?
C1 O1 Ce1 156.55(14) . . ?
C6 O3 Ce2 120.71(13) . . ?
C7 O4 Ce2 99.75(12) . . ?
C12 O6 Ce1 100.11(12) . 1_545 ?
Ce1 O7 H7A 132(2) . . ?
Ce1 O7 H7B 119(2) . . ?
H7A O7 H7B 108(2) . . ?
Ce1 O8 H8A 122(2) . . ?
Ce1 O8 H8B 121(2) . . ?
H8A O8 H8B 108(2) . . ?
Ce1 O9 H9A 123(2) . . ?
Ce1 O9 H9B 116(2) . . ?
H9A O9 H9B 105(2) . . ?
Ce1 O10 H10A 117(2) . . ?
Ce1 O10 H10B 120(2) . . ?
H10A O10 H10B 104(2) . . ?
Ce1 O11 H11A 126(2) . . ?
Ce1 O11 H11B 115(2) . . ?
H11A O11 H11B 104(2) . . ?
Ce1 O12 H12A 125(2) . . ?
Ce1 O12 H12B 115(2) . . ?
H12A O12 H12B 108(2) . . ?
Ce2 O13 H13A 123(2) . . ?
Ce2 O13 H13B 120(2) . . ?
H13A O13 H13B 107(2) . . ?
Ce2 O14 H14A 125(2) . . ?
Ce2 O14 H14B 125(2) . . ?
H14A O14 H14B 105(2) . . ?
Ce2 O15 H15A 126(2) . . ?
Ce2 O15 H15B 111(2) . . ?
H15A O15 H15B 104(3) . . ?
Ce2 O16 H16A 123(2) . . ?
Ce2 O16 H16B 120(2) . . ?
H16A O16 H16B 107(2) . . ?
Ce2 O17 H17A 130(2) . . ?
Ce2 O17 H17B 120(2) . . ?
H17A O17 H17B 102(2) . . ?
Ce2 O18 H18A 120.2(19) . . ?
Ce2 O18 H18B 119(2) . . ?
H18A O18 H18B 102(2) . . ?
C2 N1 C1 118.31(17) . . ?
C2 N2 C4 118.20(17) . . ?
C3 N3 C1 119.26(17) . . ?
C2 N4 C5 120.26(16) . . ?
C3 N4 C2 120.19(16) . . ?
C3 N4 C5 119.50(16) . . ?
C5 N5 C4 118.58(17) . . ?
C3 N6 C6 117.94(17) . . ?
C5 N7 C6 118.14(18) . . ?
C7 N8 Ce2 95.45(12) . . ?
C8 N8 Ce2 143.28(13) . . ?
C8 N8 C7 119.56(17) . . ?
C10 N9 C7 116.57(17) . . ?
C8 N10 C9 119.00(17) . . ?
C8 N11 C10 119.72(16) . . ?
C8 N11 C11 118.78(16) . . ?
C10 N11 C11 121.48(16) . . ?
C10 N12 Ce1 146.24(13) . 1_545 ?
C10 N12 C12 118.87(17) . . ?
C12 N12 Ce1 94.51(12) . 1_545 ?
C11 N13 C9 119.49(17) . . ?
C11 N14 C12 117.68(17) . . ?
O1 C1 N1 119.16(18) . . ?
O1 C1 N3 117.50(18) . . ?
N1 C1 N3 123.34(18) . . ?
N1 C2 N4 119.75(18) . . ?
N2 C2 N1 120.22(18) . . ?
N2 C2 N4 120.03(17) . . ?
N3 C3 N4 118.96(17) . . ?
N6 C3 N3 120.70(18) . . ?
N6 C3 N4 120.34(18) . . ?
O2 C4 N2 118.46(18) . . ?
O2 C4 N5 117.94(18) . . ?
N5 C4 N2 123.58(18) . . ?
N5 C5 N4 119.11(18) . . ?
N7 C5 N4 120.07(18) . . ?
N7 C5 N5 120.82(18) . . ?
O3 C6 N6 117.87(19) . . ?
O3 C6 N7 118.19(19) . . ?
N7 C6 N6 123.93(19) . . ?
O4 C7 N8 114.74(18) . . ?
O4 C7 N9 121.06(18) . . ?
N9 C7 N8 124.20(18) . . ?
N8 C8 N11 118.17(17) . . ?
N10 C8 N8 121.01(18) . . ?
N10 C8 N11 120.81(17) . . ?
O5 C9 N10 119.71(18) . . ?
O5 C9 N13 118.46(18) . . ?
N10 C9 N13 121.82(18) . . ?
N9 C10 N11 121.57(18) . . ?
N9 C10 N12 120.59(18) . . ?
N12 C10 N11 117.84(17) . . ?
N13 C11 N11 120.08(17) . . ?
N13 C11 N14 120.84(18) . . ?
N14 C11 N11 119.07(17) . . ?
O6 C12 Ce1 56.01(10) . 1_545 ?
O6 C12 N12 115.33(18) . . ?
O6 C12 N14 119.71(18) . . ?
N12 C12 Ce1 59.35(10) . 1_545 ?
N14 C12 Ce1 175.55(14) . 1_545 ?
N14 C12 N12 124.96(18) . . ?
H19A O19 H19B 111(4) . . ?
H20A O20 H20B 109(4) . . ?

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
O7 H7A O5 0.787(14) 1.907(14) 2.692(2) 175(3) 2_756 yes
O7 H7B O9 0.782(14) 2.34(2) 3.012(2) 145(3) 1_655 yes
O7 H7B O12 0.782(14) 2.65(2) 3.264(2) 136(3) 1_655 yes
O8 H8A O2 0.781(14) 1.935(17) 2.694(2) 164(3) 2_756 yes
O8 H8B O20 0.790(14) 1.984(18) 2.744(2) 161(3) 3_766 yes
O9 H9A O15 0.797(14) 2.175(19) 2.912(2) 154(3) 2_656 yes
O9 H9B N5 0.789(14) 2.021(16) 2.797(2) 168(3) 2_656 yes
O10 H10A N9 0.807(14) 2.245(17) 2.992(2) 154(3) 1_565 yes
O10 H10B N6 0.802(14) 2.030(16) 2.807(2) 163(3) 3_666 yes
O11 H11A O5 0.790(14) 2.18(2) 2.873(2) 147(3) 4_565 yes
O11 H11B N3 0.799(14) 1.866(15) 2.664(2) 176(3) 3_666 yes
O12 H12A O5 0.781(14) 2.58(2) 3.242(2) 144(3) 4_465 yes
O12 H12A N3 0.781(14) 2.60(2) 3.195(2) 134(3) 3_666 yes
O12 H12B O11 0.797(14) 2.163(15) 2.958(2) 175(3) 3_666 yes
O13 H13A O18 0.776(14) 2.063(14) 2.823(2) 166(3) 3_656 yes
O13 H13B O19 0.796(14) 1.958(18) 2.713(2) 158(3) 1_455 yes
O14 H14A N1 0.793(14) 1.964(15) 2.756(2) 176(3) 2_646 yes
O14 H14B O6 0.791(14) 2.057(19) 2.792(2) 154(3) 2_656 yes
O15 H15A O6 0.791(15) 1.996(15) 2.786(2) 177(3) 2_756 yes
O15 H15B N8 0.791(15) 2.60(3) 2.983(2) 112(2) . yes
O15 H15B N10 0.791(15) 1.999(16) 2.774(2) 166(3) . yes
O16 H16A N2 0.785(14) 2.164(16) 2.937(2) 168(3) 2_746 yes
O16 H16B O13 0.788(15) 2.180(16) 2.955(2) 168(3) 1_655 yes
O17 H17A N14 0.806(15) 1.922(16) 2.720(2) 171(3) 2_756 yes
O17 H17B O19 0.802(15) 2.60(3) 3.015(2) 114(3) . yes
O18 H18A O4 0.809(14) 1.923(16) 2.639(2) 147(2) 3_656 yes
O18 H18B O19 0.805(14) 1.903(15) 2.708(2) 179(3) . yes
O19 H19A O2 0.77(4) 1.97(4) 2.668(2) 151(4) 4_565 yes
O19 H19B O20 0.83(4) 1.97(4) 2.771(3) 162(3) . yes
O20 H20A O10 0.75(4) 2.33(4) 3.051(2) 162(4) 3_666 yes
O20 H20B N13 0.85(4) 1.94(4) 2.789(2) 178(3) 2_756 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
Ce1 O1 C1 N1 58.4(4) . . . . ?
Ce1 O1 C1 N3 -121.9(3) . . . . ?
Ce1 O6 C12 N12 1.88(18) 1_545 . . . ?
Ce1 O6 C12 N14 -178.57(15) 1_545 . . . ?
Ce1 N12 C10 N9 6.9(4) 1_545 . . . ?
Ce1 N12 C10 N11 -172.75(16) 1_545 . . . ?
Ce1 N12 C12 O6 -1.81(18) 1_545 . . . ?
Ce1 N12 C12 N14 178.66(17) 1_545 . . . ?
Ce2 O3 C6 N6 154.99(15) . . . . ?
Ce2 O3 C6 N7 -24.3(3) . . . . ?
Ce2 O4 C7 N8 6.26(19) . . . . ?
Ce2 O4 C7 N9 -173.24(16) . . . . ?
Ce2 N8 C7 O4 -6.13(18) . . . . ?
Ce2 N8 C7 N9 173.34(17) . . . . ?
Ce2 N8 C8 N10 17.4(3) . . . . ?
Ce2 N8 C8 N11 -162.42(15) . . . . ?
C1 N1 C2 N2 175.95(19) . . . . ?
C1 N1 C2 N4 -3.7(3) . . . . ?
C1 N3 C3 N4 -0.9(3) . . . . ?
C1 N3 C3 N6 179.08(19) . . . . ?
C2 N1 C1 O1 179.82(18) . . . . ?
C2 N1 C1 N3 0.1(3) . . . . ?
C2 N2 C4 O2 175.52(19) . . . . ?
C2 N2 C4 N5 -2.7(3) . . . . ?
C2 N4 C3 N3 -2.7(3) . . . . ?
C2 N4 C3 N6 177.31(18) . . . . ?
C2 N4 C5 N5 0.6(3) . . . . ?
C2 N4 C5 N7 -179.77(18) . . . . ?
C3 N3 C1 O1 -177.42(18) . . . . ?
C3 N3 C1 N1 2.3(3) . . . . ?
C3 N4 C2 N1 5.1(3) . . . . ?
C3 N4 C2 N2 -174.57(18) . . . . ?
C3 N4 C5 N5 177.78(18) . . . . ?
C3 N4 C5 N7 -2.6(3) . . . . ?
C3 N6 C6 O3 -180.0(2) . . . . ?
C3 N6 C6 N7 -0.8(3) . . . . ?
C4 N2 C2 N1 178.79(18) . . . . ?
C4 N2 C2 N4 -1.5(3) . . . . ?
C4 N5 C5 N4 -4.6(3) . . . . ?
C4 N5 C5 N7 175.79(18) . . . . ?
C5 N4 C2 N1 -177.73(18) . . . . ?
C5 N4 C2 N2 2.6(3) . . . . ?
C5 N4 C3 N3 -179.87(18) . . . . ?
C5 N4 C3 N6 0.1(3) . . . . ?
C5 N5 C4 O2 -172.35(18) . . . . ?
C5 N5 C4 N2 5.9(3) . . . . ?
C5 N7 C6 O3 177.5(2) . . . . ?
C5 N7 C6 N6 -1.7(3) . . . . ?
C6 N6 C3 N3 -178.53(19) . . . . ?
C6 N6 C3 N4 1.4(3) . . . . ?
C6 N7 C5 N4 3.3(3) . . . . ?
C6 N7 C5 N5 -177.15(19) . . . . ?
C7 N8 C8 N10 177.97(18) . . . . ?
C7 N8 C8 N11 -1.9(3) . . . . ?
C7 N9 C10 N11 3.5(3) . . . . ?
C7 N9 C10 N12 -176.18(18) . . . . ?
C8 N8 C7 O4 -174.59(18) . . . . ?
C8 N8 C7 N9 4.9(3) . . . . ?
C8 N10 C9 O5 177.78(18) . . . . ?
C8 N10 C9 N13 -0.9(3) . . . . ?
C8 N11 C10 N9 -0.9(3) . . . . ?
C8 N11 C10 N12 178.78(17) . . . . ?
C8 N11 C11 N13 0.8(3) . . . . ?
C8 N11 C11 N14 -178.38(17) . . . . ?
C9 N10 C8 N8 -178.41(18) . . . . ?
C9 N10 C8 N11 1.4(3) . . . . ?
C9 N13 C11 N11 -0.3(3) . . . . ?
C9 N13 C11 N14 178.85(18) . . . . ?
C10 N9 C7 O4 173.84(18) . . . . ?
C10 N9 C7 N8 -5.6(3) . . . . ?
C10 N11 C8 N8 0.0(3) . . . . ?
C10 N11 C8 N10 -179.83(17) . . . . ?
C10 N11 C11 N13 179.22(18) . . . . ?
C10 N11 C11 N14 0.0(3) . . . . ?
C10 N12 C12 Ce1 -174.8(2) . . . 1_545 ?
C10 N12 C12 O6 -176.56(17) . . . . ?
C10 N12 C12 N14 3.9(3) . . . . ?
C11 N11 C8 N8 178.45(17) . . . . ?
C11 N11 C8 N10 -1.4(3) . . . . ?
C11 N11 C10 N9 -179.29(18) . . . . ?
C11 N11 C10 N12 0.4(3) . . . . ?
C11 N13 C9 O5 -178.36(18) . . . . ?
C11 N13 C9 N10 0.4(3) . . . . ?
C11 N14 C12 O6 177.05(18) . . . . ?
C11 N14 C12 N12 -3.5(3) . . . . ?
C12 N12 C10 N9 177.49(18) . . . . ?
C12 N12 C10 N11 -2.2(3) . . . . ?
C12 N14 C11 N11 1.4(3) . . . . ?
C12 N14 C11 N13 -177.81(18) . . . . ?

_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_dycy
_database_code_depnum_ccdc_archive 'CCDC 2178360'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2022-06-10 deposited with the CCDC.	2022-09-01 downloaded from the CCDC.
;
_audit_creation_date             2022-06-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H14 Dy N7 O10'
_chemical_formula_sum            'C6 H14 Dy N7 O10'
_chemical_formula_weight         506.74
_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 0.0137 0.0067 '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'
Dy Dy -5.9987 12.4498 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   11.8702(7)
_cell_length_b                   6.7923(4)
_cell_length_c                   16.6124(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.689(2)
_cell_angle_gamma                90
_cell_volume                     1336.62(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9535
_cell_measurement_temperature    150
_cell_measurement_theta_max      57.039
_cell_measurement_theta_min      3.868
_shelx_estimated_absorpt_T_max   0.472
_shelx_estimated_absorpt_T_min   0.126
_exptl_absorpt_coefficient_mu    29.415
_exptl_absorpt_correction_T_max  0.2043
_exptl_absorpt_correction_T_min  0.0585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1621 before and 0.0989 after correction.
The Ratio of minimum to maximum transmission is 0.2863.
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    2.518
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             980
_exptl_crystal_size_max          0.12
_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 Venture diffractometer equipped with a Photon III CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_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            35064
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.072
_diffrn_reflns_theta_min         3.867
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.42
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_current           2.85
_diffrn_source_power             0.19921500000000003
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_voltage           69.9
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2704
_reflns_number_total             2731
_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 (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         1.327
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.160
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         2731
_refine_ls_number_restraints     35
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0247
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0493P)²+0.6862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0648
_refine_ls_wR_factor_ref         0.0651
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 O4-H4A = O4-H4B = O5-H5A = O5-H5B = O6-H6A = O6-H6B = O7-H7A = O7-H7B = O8-
 H8A = O8-H8B = O9-H9A = O9-H9B = O10-H10A = O10-H10B
 0.85 with sigma of 0.02
 H4A-H4B \\sim H5A-H5B \\sim H6A-H6B \\sim H7A-H7B \\sim H8A-H8B \\sim H9A-H9B
\\sim H10A-H10B
 with sigma of 0.02
;
_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
Dy1 Dy 0.51844(2) 0.63831(2) 0.17636(2) 0.02181(9) Uani 1 1 d . . . . .
O1 O 0.66330(15) 0.7766(3) 0.26967(12) 0.0293(4) Uani 1 1 d . . . . .
O2 O 0.17832(16) 0.5915(3) 0.45155(13) 0.0260(4) Uani 1 1 d . . . . .
O3 O 0.65210(18) 0.8522(3) 0.67861(13) 0.0267(4) Uani 1 1 d . . . . .
O4 O 0.58200(18) 0.9361(3) 0.10625(13) 0.0327(4) Uani 1 1 d D . . . .
H4A H 0.614(3) 0.938(6) 0.0625(16) 0.044(11) Uiso 1 1 d D . . . .
H4B H 0.573(5) 1.055(4) 0.118(3) 0.077(17) Uiso 1 1 d D . . . .
O5 O 0.67943(17) 0.5884(3) 0.10786(13) 0.0284(4) Uani 1 1 d D . . . .
H5A H 0.725(3) 0.677(4) 0.094(3) 0.045(11) Uiso 1 1 d D . . . .
H5B H 0.721(3) 0.485(4) 0.108(3) 0.052(12) Uiso 1 1 d D . . . .
O6 O 0.6027(2) 0.3562(3) 0.24647(15) 0.0295(5) Uani 1 1 d D . . . .
H6A H 0.584(3) 0.309(6) 0.2901(17) 0.040(10) Uiso 1 1 d D . . . .
H6B H 0.6704(18) 0.329(6) 0.244(2) 0.040(11) Uiso 1 1 d D . . . .
O7 O 0.50165(19) 0.3468(3) 0.08712(14) 0.0278(4) Uani 1 1 d D . . . .
H7A H 0.535(3) 0.345(6) 0.0431(18) 0.049(13) Uiso 1 1 d D . . . .
H7B H 0.439(2) 0.292(8) 0.074(3) 0.063(15) Uiso 1 1 d D . . . .
O8 O 0.39283(16) 0.7040(3) 0.05584(12) 0.0272(4) Uani 1 1 d D . . . .
H8A H 0.327(2) 0.658(5) 0.053(3) 0.035(11) Uiso 1 1 d D . . . .
H8B H 0.382(4) 0.827(3) 0.049(3) 0.057(15) Uiso 1 1 d D . . . .
O9 O 0.35428(15) 0.4600(3) 0.20173(12) 0.0273(4) Uani 1 1 d D . . . .
H9A H 0.293(2) 0.519(5) 0.195(2) 0.046(11) Uiso 1 1 d D . . . .
H9B H 0.348(4) 0.384(5) 0.240(2) 0.050(14) Uiso 1 1 d D . . . .
O10 O 0.39851(18) 0.9137(3) 0.19906(13) 0.0305(4) Uani 1 1 d D . . . .
H10A H 0.365(3) 0.978(5) 0.1626(15) 0.039(10) Uiso 1 1 d D . . . .
H10B H 0.394(4) 0.978(6) 0.2420(14) 0.049(11) Uiso 1 1 d D . . . .
N1 N 0.5053(2) 0.6972(4) 0.32670(13) 0.0255(4) Uani 1 1 d . . . . .
N2 N 0.67090(18) 0.8013(4) 0.40660(14) 0.0248(4) Uani 1 1 d . . . . .
N3 N 0.3387(2) 0.6333(3) 0.38664(17) 0.0260(5) Uani 1 1 d . . . . .
N4 N 0.49938(17) 0.7375(3) 0.46625(13) 0.0225(4) Uani 1 1 d . . . . .
N5 N 0.6626(2) 0.8408(3) 0.54327(16) 0.0249(5) Uani 1 1 d . . . . .
N6 N 0.3310(2) 0.6800(4) 0.53019(15) 0.0251(4) Uani 1 1 d . . . . .
N7 N 0.49015(18) 0.7733(3) 0.60738(13) 0.0248(4) Uani 1 1 d . . . . .
C1 C 0.6151(2) 0.7601(4) 0.33480(16) 0.0249(5) Uani 1 1 d . . . . .
C2 C 0.4455(2) 0.6870(4) 0.39142(17) 0.0239(5) Uani 1 1 d . . . . .
C3 C 0.6137(2) 0.7933(4) 0.47228(16) 0.0232(5) Uani 1 1 d . . . . .
C4 C 0.2827(3) 0.6350(4) 0.4557(2) 0.0252(6) Uani 1 1 d . . . . .
C5 C 0.4392(2) 0.7312(4) 0.53579(15) 0.0226(5) Uani 1 1 d . . . . .
C6 C 0.6021(2) 0.8218(4) 0.61046(18) 0.0249(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
Dy1 O1 2.4287(19) . ?
Dy1 O4 2.476(2) . ?
Dy1 O5 2.311(2) . ?
Dy1 O6 2.424(2) . ?
Dy1 O7 2.474(2) . ?
Dy1 O8 2.459(2) . ?
Dy1 O9 2.3552(18) . ?
Dy1 O10 2.395(2) . ?
Dy1 N1 2.544(2) . ?
O1 C1 1.261(3) . ?
O2 C4 1.272(4) . ?
O3 C6 1.261(4) . ?
O4 H4A 0.842(19) . ?
O4 H4B 0.840(19) . ?
O5 H5A 0.853(19) . ?
O5 H5B 0.857(19) . ?
O6 H6A 0.838(18) . ?
O6 H6B 0.829(18) . ?
O7 H7A 0.855(19) . ?
O7 H7B 0.841(19) . ?
O8 H8A 0.845(19) . ?
O8 H8B 0.852(19) . ?
O9 H9A 0.835(18) . ?
O9 H9B 0.829(19) . ?
O10 H10A 0.827(18) . ?
O10 H10B 0.839(19) . ?
N1 C1 1.370(4) . ?
N1 C2 1.328(4) . ?
N2 C1 1.356(4) . ?
N2 C3 1.323(3) . ?
N3 C2 1.316(4) . ?
N3 C4 1.362(4) . ?
N4 C2 1.404(4) . ?
N4 C3 1.406(3) . ?
N4 C5 1.398(3) . ?
N5 C3 1.320(4) . ?
N5 C6 1.372(4) . ?
N6 C4 1.365(4) . ?
N6 C5 1.328(3) . ?
N7 C5 1.331(3) . ?
N7 C6 1.366(4) . ?

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 Dy1 O4 76.09(7) . . ?
O1 Dy1 O7 135.92(7) . . ?
O1 Dy1 O8 144.77(7) . . ?
O1 Dy1 N1 53.01(7) . . ?
O4 Dy1 N1 111.92(8) . . ?
O5 Dy1 O1 78.29(7) . . ?
O5 Dy1 O4 66.51(7) . . ?
O5 Dy1 O6 78.01(8) . . ?
O5 Dy1 O7 67.97(8) . . ?
O5 Dy1 O8 95.91(7) . . ?
O5 Dy1 O9 137.11(7) . . ?
O5 Dy1 O10 135.29(8) . . ?
O5 Dy1 N1 127.69(8) . . ?
O6 Dy1 O1 75.28(8) . . ?
O6 Dy1 O4 137.98(8) . . ?
O6 Dy1 O7 70.74(8) . . ?
O6 Dy1 O8 138.09(8) . . ?
O6 Dy1 N1 72.67(8) . . ?
O7 Dy1 O4 112.78(7) . . ?
O7 Dy1 N1 134.95(8) . . ?
O8 Dy1 O4 69.88(7) . . ?
O8 Dy1 O7 68.65(7) . . ?
O8 Dy1 N1 134.31(7) . . ?
O9 Dy1 O1 130.13(7) . . ?
O9 Dy1 O4 141.71(7) . . ?
O9 Dy1 O6 80.10(7) . . ?
O9 Dy1 O7 70.13(7) . . ?
O9 Dy1 O8 76.92(7) . . ?
O9 Dy1 O10 82.32(7) . . ?
O9 Dy1 N1 78.54(8) . . ?
O10 Dy1 O1 90.06(7) . . ?
O10 Dy1 O4 68.79(7) . . ?
O10 Dy1 O6 140.58(8) . . ?
O10 Dy1 O7 133.92(8) . . ?
O10 Dy1 O8 69.58(7) . . ?
O10 Dy1 N1 69.39(8) . . ?
C1 O1 Dy1 99.86(16) . . ?
Dy1 O4 H4A 126(3) . . ?
Dy1 O4 H4B 129(3) . . ?
H4A O4 H4B 105(3) . . ?
Dy1 O5 H5A 127(3) . . ?
Dy1 O5 H5B 127(3) . . ?
H5A O5 H5B 102(3) . . ?
Dy1 O6 H6A 127(3) . . ?
Dy1 O6 H6B 121(3) . . ?
H6A O6 H6B 106(3) . . ?
Dy1 O7 H7A 120(3) . . ?
Dy1 O7 H7B 123(3) . . ?
H7A O7 H7B 103(3) . . ?
Dy1 O8 H8A 119(3) . . ?
Dy1 O8 H8B 112(3) . . ?
H8A O8 H8B 103(3) . . ?
Dy1 O9 H9A 117(3) . . ?
Dy1 O9 H9B 125(3) . . ?
H9A O9 H9B 106(3) . . ?
Dy1 O10 H10A 124(2) . . ?
Dy1 O10 H10B 128(3) . . ?
H10A O10 H10B 107(3) . . ?
C1 N1 Dy1 91.57(16) . . ?
C2 N1 Dy1 148.9(2) . . ?
C2 N1 C1 119.4(2) . . ?
C3 N2 C1 118.0(2) . . ?
C2 N3 C4 117.8(3) . . ?
C2 N4 C3 120.8(2) . . ?
C5 N4 C2 119.7(2) . . ?
C5 N4 C3 119.5(2) . . ?
C3 N5 C6 118.7(2) . . ?
C5 N6 C4 118.0(2) . . ?
C5 N7 C6 118.1(2) . . ?
O1 C1 N1 115.1(2) . . ?
O1 C1 N2 120.9(2) . . ?
N2 C1 N1 124.0(2) . . ?
N1 C2 N4 117.8(2) . . ?
N3 C2 N1 121.9(3) . . ?
N3 C2 N4 120.2(2) . . ?
N2 C3 N4 119.8(2) . . ?
N5 C3 N2 120.5(2) . . ?
N5 C3 N4 119.7(2) . . ?
O2 C4 N3 118.7(3) . . ?
O2 C4 N6 116.8(3) . . ?
N3 C4 N6 124.5(3) . . ?
N6 C5 N4 119.6(2) . . ?
N6 C5 N7 120.1(2) . . ?
N7 C5 N4 120.3(2) . . ?
O3 C6 N5 118.3(3) . . ?
O3 C6 N7 118.3(3) . . ?
N7 C6 N5 123.4(3) . . ?

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 0.842(19) 2.049(19) 2.885(3) 172(4) 4_675 yes
O4 H4B O7 0.840(19) 2.21(3) 2.959(3) 149(5) 1_565 yes
O5 H5A N6 0.853(19) 1.95(2) 2.771(3) 161(4) 4_675 yes
O5 H5B N2 0.857(19) 1.82(2) 2.659(3) 166(4) 2_645 yes
O6 H6A N7 0.838(18) 2.042(19) 2.868(3) 169(4) 3_666 yes
O6 H6B O1 0.829(18) 2.032(18) 2.860(3) 176(4) 2_645 yes
O7 H7A O8 0.855(19) 1.93(2) 2.777(3) 171(4) 3_665 yes
O7 H7B O2 0.841(19) 1.98(3) 2.794(3) 162(6) 2_545 yes
O8 H8A N5 0.845(19) 1.94(2) 2.745(3) 158(3) 4_575 yes
O8 H8B O2 0.852(19) 1.94(3) 2.765(3) 164(5) 2 yes
O9 H9A O3 0.835(18) 1.888(19) 2.723(3) 178(4) 4_575 yes
O9 H9B O3 0.829(19) 2.095(19) 2.911(3) 168(4) 3_666 yes
O10 H10A O2 0.827(18) 2.08(2) 2.874(3) 160(3) 2 yes
O10 H10B O3 0.839(19) 1.86(2) 2.679(3) 164(4) 3_676 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
Dy1 O1 C1 N1 -6.5(3) . . . . ?
Dy1 O1 C1 N2 173.0(2) . . . . ?
Dy1 N1 C1 O1 6.1(3) . . . . ?
Dy1 N1 C1 N2 -173.3(2) . . . . ?
Dy1 N1 C2 N3 -5.9(6) . . . . ?
Dy1 N1 C2 N4 174.7(3) . . . . ?
C1 N1 C2 N3 177.9(3) . . . . ?
C1 N1 C2 N4 -1.5(4) . . . . ?
C1 N2 C3 N4 1.9(4) . . . . ?
C1 N2 C3 N5 -176.9(2) . . . . ?
C2 N1 C1 O1 -175.9(3) . . . . ?
C2 N1 C1 N2 4.7(4) . . . . ?
C2 N3 C4 O2 177.1(2) . . . . ?
C2 N3 C4 N6 -3.1(4) . . . . ?
C2 N4 C3 N2 1.0(4) . . . . ?
C2 N4 C3 N5 179.8(2) . . . . ?
C2 N4 C5 N6 -0.9(4) . . . . ?
C2 N4 C5 N7 178.1(2) . . . . ?
C3 N2 C1 O1 175.8(3) . . . . ?
C3 N2 C1 N1 -4.8(4) . . . . ?
C3 N4 C2 N1 -1.2(4) . . . . ?
C3 N4 C2 N3 179.4(2) . . . . ?
C3 N4 C5 N6 179.5(2) . . . . ?
C3 N4 C5 N7 -1.5(4) . . . . ?
C3 N5 C6 O3 174.4(2) . . . . ?
C3 N5 C6 N7 -6.3(4) . . . . ?
C4 N3 C2 N1 -177.3(3) . . . . ?
C4 N3 C2 N4 2.1(4) . . . . ?
C4 N6 C5 N4 0.1(4) . . . . ?
C4 N6 C5 N7 -179.0(2) . . . . ?
C5 N4 C2 N1 179.2(2) . . . . ?
C5 N4 C2 N3 -0.2(4) . . . . ?
C5 N4 C3 N2 -179.4(2) . . . . ?
C5 N4 C3 N5 -0.7(4) . . . . ?
C5 N6 C4 O2 -178.2(2) . . . . ?
C5 N6 C4 N3 2.0(4) . . . . ?
C5 N7 C6 O3 -176.5(2) . . . . ?
C5 N7 C6 N5 4.1(4) . . . . ?
C6 N5 C3 N2 -177.0(3) . . . . ?
C6 N5 C3 N4 4.3(4) . . . . ?
C6 N7 C5 N4 -0.2(4) . . . . ?
C6 N7 C5 N6 178.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
