# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_160930_SM_YbCuida_LTemp_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1878174'
loop_
_audit_author_name
_audit_author_address
'Sebasti?n Mart?nez'
;Facultad de Qu?mica , Universidad de la Rep?blica
Uruguay
;
_audit_update_record             
;
2018-11-09 deposited with the CCDC.	2019-06-11 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT978_cu_160930_SM_YbCuida_LTemp_0m_a 
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: It was not possible to collect high quality data below 0.83 Ang. 
As a consequence, residual density from C-C bonds is not observed.
;
# end Validation Reply Form 

_audit_creation_method           'SHELXL-2016/6 - OLEX2'
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'Ytterbium Copper (II) Iminodiacetate hydrate'
_chemical_name_common            YbCuIDA
_chemical_melting_point          'not measured'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H30 Cu3 N6 O24 Yb2'
_chemical_formula_weight         1323.21

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'
Cu Cu -1.9646 0.5888 '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'

_space_group_crystal_system      trigonal
_space_group_IT_number           165
_space_group_name_H-M_alt        'P -3 c 1'
_space_group_name_Hall           '-P 3 2"c'

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

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

_cell_length_a                   13.2638(3)
_cell_length_b                   13.2638(3)
_cell_length_c                   14.1414(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2154.56(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    124
_cell_measurement_theta_min      11.5807
_cell_measurement_theta_max      57.0696

_exptl_crystal_description       Hexagonal
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.040
_exptl_crystal_F_000             1270
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.094
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.058
_exptl_absorpt_coefficient_mu    10.111
_shelx_estimated_absorpt_T_min   0.450
_shelx_estimated_absorpt_T_max   0.592
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_T_max  0.59
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   
;
SADABS (Krause et al, J. Appl. Cryst. 48, 3-10)
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec microsource Type HB030R1'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and \j scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            50552
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0954
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.848
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_full        66.589
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1278
_reflns_number_gt                959
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Instrument Service vV6.2.1'
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material  -
_refine_special_details          
;
 All heavy atoms where refined anisotropically. 
 Hydrogen atoms bonded to C1 and C3 where located geometrically and
 refined using AFIX 23. Hydrogen atom bonded to N1 was located 
 geometrically and refined using AFIX 13
 Disordered electron density from the cavities was 
 removed using OLEX2 solvent mask procedure. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0205P)²+6.1833P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1278
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0538
_refine_ls_wR_factor_gt          0.0495
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Yb1 Yb 0.666667 0.333333 0.83403(2) 0.00896(11) Uani 1 3 d S T P . .
Cu1 Cu 0.500000 0.500000 0.500000 0.0143(2) Uani 1 2 d S . P . .
O1 O 0.6220(2) 0.4350(2) 0.73244(19) 0.0204(7) Uani 1 1 d . . . . .
O2 O 0.5991(3) 0.5257(2) 0.6108(2) 0.0198(6) Uani 1 1 d . . . . .
O3 O 0.5503(3) 0.3584(3) 0.4420(2) 0.0212(7) Uani 1 1 d . . . . .
O4 O 0.4393(3) 0.1919(3) 0.3716(2) 0.0291(8) Uani 1 1 d . . . . .
N1 N 0.3890(3) 0.3466(3) 0.5599(2) 0.0123(7) Uani 1 1 d . . . . .
H1 H 0.319230 0.349448 0.583097 0.015 Uiso 1 1 calc R U . . .
C1 C 0.4488(4) 0.3295(4) 0.6422(3) 0.0196(9) Uani 1 1 d . . . . .
H1A H 0.461969 0.263643 0.629045 0.024 Uiso 1 1 calc R U . . .
H1B H 0.398107 0.309211 0.698635 0.024 Uiso 1 1 calc R U . . .
C2 C 0.5640(4) 0.4370(4) 0.6630(2) 0.0132(7) Uani 1 1 d . . . . .
C3 C 0.3512(4) 0.2524(3) 0.4895(3) 0.0165(9) Uani 1 1 d . . . . .
H3A H 0.291396 0.252743 0.447764 0.020 Uiso 1 1 calc R U . . .
H3B H 0.315663 0.176382 0.522333 0.020 Uiso 1 1 calc R U . . .
C4 C 0.4532(4) 0.2677(4) 0.4302(3) 0.0172(9) 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
Yb1 O1 2.243(3) 3_665 ?
Yb1 O1 2.243(3) 2_655 ?
Yb1 O1 2.243(3) . ?
Yb1 O3 2.311(3) 11_656 ?
Yb1 O3 2.311(3) 12_556 ?
Yb1 O3 2.311(3) 10_666 ?
Yb1 O4 2.690(3) 11_656 ?
Yb1 O4 2.690(4) 10_666 ?
Yb1 O4 2.690(3) 12_556 ?
Cu1 O2 1.962(3) . ?
Cu1 O2 1.962(3) 7_666 ?
Cu1 N1 2.007(3) 7_666 ?
Cu1 N1 2.008(3) . ?
Cu1 O3 2.428(3) . ?
Cu1 O3 2.428(3) 7_666 ?
O1 C2 1.256(4) . ?
O2 C2 1.265(5) . ?
O3 C4 1.258(5) . ?
O4 C4 1.244(5) . ?
N1 C3 1.475(5) . ?
N1 C1 1.489(5) . ?
N1 H1 1.0000 . ?
C1 C2 1.508(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C3 C4 1.517(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?

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 O1 83.38(11) 3_665 2_655 ?
O1 Yb1 O1 83.38(11) 3_665 . ?
O1 Yb1 O1 83.38(11) 2_655 . ?
O1 Yb1 O3 81.50(11) 3_665 11_656 ?
O1 Yb1 O3 129.89(10) 2_655 11_656 ?
O1 Yb1 O3 140.92(10) . 11_656 ?
O1 Yb1 O3 140.92(10) 3_665 12_556 ?
O1 Yb1 O3 81.50(11) 2_655 12_556 ?
O1 Yb1 O3 129.89(10) . 12_556 ?
O3 Yb1 O3 81.08(11) 11_656 12_556 ?
O1 Yb1 O3 129.89(10) 3_665 10_666 ?
O1 Yb1 O3 140.92(10) 2_655 10_666 ?
O1 Yb1 O3 81.49(11) . 10_666 ?
O3 Yb1 O3 81.08(11) 11_656 10_666 ?
O3 Yb1 O3 81.08(11) 12_556 10_666 ?
O1 Yb1 O4 72.44(10) 3_665 11_656 ?
O1 Yb1 O4 78.70(10) 2_655 11_656 ?
O1 Yb1 O4 151.26(10) . 11_656 ?
O3 Yb1 O4 51.19(10) 11_656 11_656 ?
O3 Yb1 O4 69.35(10) 12_556 11_656 ?
O3 Yb1 O4 126.03(10) 10_666 11_656 ?
O1 Yb1 O4 78.70(10) 3_665 10_666 ?
O1 Yb1 O4 151.26(10) 2_655 10_666 ?
O1 Yb1 O4 72.44(10) . 10_666 ?
O3 Yb1 O4 69.35(10) 11_656 10_666 ?
O3 Yb1 O4 126.03(10) 12_556 10_666 ?
O3 Yb1 O4 51.19(10) 10_666 10_666 ?
O4 Yb1 O4 116.21(5) 11_656 10_666 ?
O1 Yb1 O4 151.26(10) 3_665 12_556 ?
O1 Yb1 O4 72.44(10) 2_655 12_556 ?
O1 Yb1 O4 78.70(10) . 12_556 ?
O3 Yb1 O4 126.03(10) 11_656 12_556 ?
O3 Yb1 O4 51.19(10) 12_556 12_556 ?
O3 Yb1 O4 69.35(10) 10_666 12_556 ?
O4 Yb1 O4 116.21(5) 11_656 12_556 ?
O4 Yb1 O4 116.21(5) 10_666 12_556 ?
O2 Cu1 O2 180.0 . 7_666 ?
O2 Cu1 N1 94.17(12) . 7_666 ?
O2 Cu1 N1 85.83(12) 7_666 7_666 ?
O2 Cu1 N1 85.83(12) . . ?
O2 Cu1 N1 94.17(12) 7_666 . ?
N1 Cu1 N1 180.0 7_666 . ?
O2 Cu1 O3 89.14(12) . . ?
O2 Cu1 O3 90.86(12) 7_666 . ?
N1 Cu1 O3 107.18(11) 7_666 . ?
N1 Cu1 O3 72.82(11) . . ?
O2 Cu1 O3 90.86(12) . 7_666 ?
O2 Cu1 O3 89.14(12) 7_666 7_666 ?
N1 Cu1 O3 72.82(11) 7_666 7_666 ?
N1 Cu1 O3 107.18(11) . 7_666 ?
O3 Cu1 O3 180.0 . 7_666 ?
C2 O1 Yb1 149.6(3) . . ?
C2 O2 Cu1 113.7(3) . . ?
C4 O3 Yb1 102.2(3) . 10_665 ?
C4 O3 Cu1 103.8(3) . . ?
Yb1 O3 Cu1 142.77(13) 10_665 . ?
C4 O4 Yb1 84.6(3) . 10_665 ?
C3 N1 C1 112.4(3) . . ?
C3 N1 Cu1 109.8(2) . . ?
C1 N1 Cu1 107.9(2) . . ?
C3 N1 H1 108.9 . . ?
C1 N1 H1 108.9 . . ?
Cu1 N1 H1 108.9 . . ?
N1 C1 C2 111.9(3) . . ?
N1 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
O1 C2 O2 122.1(5) . . ?
O1 C2 C1 118.3(4) . . ?
O2 C2 C1 119.6(3) . . ?
N1 C3 C4 110.9(3) . . ?
N1 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.0 . . ?
O4 C4 O3 121.9(4) . . ?
O4 C4 C3 119.9(4) . . ?
O3 C4 C3 118.2(4) . . ?
O4 C4 Yb1 69.7(2) . 10_665 ?
O3 C4 Yb1 52.3(2) . 10_665 ?
C3 C4 Yb1 170.4(3) . 10_665 ?

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
C3 N1 C1 C2 129.4(4) . . . . ?
Cu1 N1 C1 C2 8.2(4) . . . . ?
Yb1 O1 C2 O2 -155.3(4) . . . . ?
Yb1 O1 C2 C1 24.7(7) . . . . ?
Cu1 O2 C2 O1 173.9(3) . . . . ?
Cu1 O2 C2 C1 -6.1(4) . . . . ?
N1 C1 C2 O1 178.2(3) . . . . ?
N1 C1 C2 O2 -1.7(5) . . . . ?
C1 N1 C3 C4 -77.2(4) . . . . ?
Cu1 N1 C3 C4 43.0(4) . . . . ?
Yb1 O4 C4 O3 -0.1(4) 10_665 . . . ?
Yb1 O4 C4 C3 179.4(3) 10_665 . . . ?
Yb1 O3 C4 O4 0.1(5) 10_665 . . . ?
Cu1 O3 C4 O4 153.3(3) . . . . ?
Yb1 O3 C4 C3 -179.4(3) 10_665 . . . ?
Cu1 O3 C4 C3 -26.2(4) . . . . ?
Cu1 O3 C4 Yb1 153.2(2) . . . 10_665 ?
N1 C3 C4 O4 175.0(4) . . . . ?
N1 C3 C4 O3 -5.5(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O4 1.00 1.97 2.879(4) 150.1 9_556

_refine_diff_density_max         0.638
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.109



