# 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 2017

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

data_DUT-102
_database_code_depnum_ccdc_archive 'CCDC 1524213'
_audit_update_record             
;
2016-12-23 deposited with the CCDC.
2017-09-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H25 N2 O16 Tb'
_chemical_formula_weight         648.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   13.0587(7)
_cell_length_b                   11.2253(6)
_cell_length_c                   17.2297(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 120.987(3)
_cell_angle_gamma                90.00
_cell_volume                     2165.21(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5823
_cell_measurement_theta_min      1.82
_cell_measurement_theta_max      29.15

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.989
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1288
_exptl_absorpt_coefficient_mu    3.353
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4760
_exptl_absorpt_correction_T_max  0.5258
_exptl_absorpt_process_details   'Higashi (1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 'Bruker SMART CCD area'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none'
_diffrn_reflns_number            18008
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         29.15
_reflns_number_total             5823
_reflns_number_gt                4863
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0303P)²+2.5273P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       0
_refine_ls_number_reflns         5823
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0690
_refine_ls_wR_factor_gt          0.0631
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Tb1 Tb 0.243849(10) 0.881094(10) 0.751456(7) 0.01739(5) Uani 1 1 d . . .
O1 O 0.38090(18) 0.71313(18) 0.81110(13) 0.0265(4) Uani 1 1 d . . .
O2 O 0.29161(17) 0.74940(17) 0.88686(13) 0.0229(4) Uani 1 1 d . . .
O3 O 0.5274(2) 0.82473(18) 1.03809(15) 0.0344(5) Uani 1 1 d . . .
O4 O 0.5561(4) 0.7383(2) 1.16102(18) 0.0811(12) Uani 1 1 d . . .
O5 O 0.20209(17) 0.75268(17) 0.61745(13) 0.0232(4) Uani 1 1 d . . .
O6 O 0.10947(18) 0.71120(18) 0.68970(13) 0.0258(4) Uani 1 1 d . . .
O7 O -0.03484(19) 0.82365(17) 0.46192(14) 0.0266(4) Uani 1 1 d . . .
O8 O -0.0352(2) 0.74203(19) 0.34481(15) 0.0395(6) Uani 1 1 d . . .
O9 O 0.3816(2) 0.9273(2) 0.70298(14) 0.0321(5) Uani 1 1 d . . .
H9A H 0.4294 0.9773 0.7371 0.038 Uiso 1 1 d R . .
H9B H 0.4446 0.8956 0.7595 0.038 Uiso 1 1 d R . .
O10 O 0.40880(19) 0.95955(18) 0.88479(13) 0.0318(5) Uani 1 1 d . . .
H10A H 0.3998 1.0313 0.8878 0.038 Uiso 1 1 d R . .
H10B H 0.4520 0.9207 0.9104 0.038 Uiso 1 1 d R . .
O11 O 0.10737(19) 0.91577(19) 0.80248(14) 0.0294(5) Uani 1 1 d . . .
H11A H 0.0549 0.9617 0.7676 0.035 Uiso 1 1 d R . .
H11B H 0.0478 0.8843 0.7947 0.035 Uiso 1 1 d R . .
O12 O 0.23703(19) 1.1010(2) 0.75187(13) 0.0363(6) Uani 1 1 d . . .
H12A H 0.1681 1.1237 0.7186 0.044 Uiso 1 1 d R . .
H12B H 0.2928 1.1432 0.7881 0.044 Uiso 1 1 d R . .
O13 O 0.0783(2) 0.95746(18) 0.61474(13) 0.0319(5) Uani 1 1 d . . .
H13A H 0.0906 1.0274 0.6085 0.038 Uiso 1 1 d R . .
H13B H 0.0221 0.9733 0.6247 0.038 Uiso 1 1 d R . .
C1 C 0.5301(3) 0.7352(3) 1.0811(2) 0.0313(7) Uani 1 1 d . . .
C2 C 0.5093(3) 0.6142(2) 1.03671(18) 0.0200(5) Uani 1 1 d . . .
C3 C 0.4406(2) 0.5961(2) 0.94309(18) 0.0179(5) Uani 1 1 d . . .
C4 C 0.4324(2) 0.4831(2) 0.90794(18) 0.0211(5) Uani 1 1 d . . .
H4 H 0.3866 0.4720 0.8456 0.025 Uiso 1 1 calc R . .
C5 C 0.3677(2) 0.6929(2) 0.87735(17) 0.0183(5) Uani 1 1 d . . .
C6 C 0.0619(2) 0.4825(2) 0.59195(18) 0.0197(5) Uani 1 1 d . . .
H6 H 0.1040 0.4711 0.6543 0.024 Uiso 1 1 calc R . .
C7 C 0.0567(2) 0.5961(2) 0.55791(18) 0.0174(5) Uani 1 1 d . . .
C8 C -0.0060(2) 0.6144(2) 0.46446(18) 0.0175(5) Uani 1 1 d . . .
C9 C -0.0247(2) 0.7363(2) 0.42132(19) 0.0213(5) Uani 1 1 d . . .
C10 C 0.1261(2) 0.6933(2) 0.62458(18) 0.0185(5) Uani 1 1 d . . .
N1 N 0.7275(3) 0.5108(3) 0.4895(2) 0.0521(8) Uani 1 1 d . . .
H1A H 0.6858 0.4752 0.4383 0.063 Uiso 1 1 d R . .
H1B H 0.7627 0.4701 0.5388 0.063 Uiso 1 1 d R . .
N2 N 0.7557(3) 0.8720(3) 0.5002(3) 0.0550(9) Uani 1 1 d . . .
H2B H 0.7599 0.9485 0.5024 0.066 Uiso 1 1 d R . .
C11 C 0.8118(4) 0.8088(4) 0.5760(3) 0.0550(10) Uani 1 1 d . . .
H11 H 0.8566 0.8479 0.6311 0.066 Uiso 1 1 calc R . .
C12 C 0.8051(3) 0.6878(4) 0.5745(3) 0.0461(9) Uani 1 1 d . . .
H12 H 0.8455 0.6448 0.6281 0.055 Uiso 1 1 calc R . .
C13 C 0.7378(3) 0.6289(3) 0.4925(3) 0.0386(8) Uani 1 1 d . . .
C14 C 0.6813(4) 0.6980(4) 0.4131(3) 0.0501(10) Uani 1 1 d . . .
H14 H 0.6373 0.6620 0.3566 0.060 Uiso 1 1 calc R . .
C15 C 0.6923(4) 0.8172(4) 0.4207(3) 0.0574(11) Uani 1 1 d . . .
H15 H 0.6542 0.8631 0.3683 0.069 Uiso 1 1 calc R . .
O14 O 0.4431(2) 0.5862(2) 0.70161(17) 0.0442(6) Uani 1 1 d . . .
H14A H 0.4789 0.6400 0.6869 0.053 Uiso 1 1 d R . .
H14B H 0.4107 0.6133 0.7213 0.053 Uiso 1 1 d R . .
O15 O 0.9278(2) 0.0586(2) 0.70450(16) 0.0445(6) Uani 1 1 d . . .
O16 O 0.7621(3) 0.1201(2) 0.5002(2) 0.0635(9) Uani 1 1 d . . .
H15A H 0.9298 0.0903 0.6596 0.076 Uiso 1 1 d R . .
H15B H 0.9107 0.1026 0.7368 0.076 Uiso 1 1 d R . .
H16A H 0.7396 0.1656 0.5285 0.076 Uiso 1 1 d R . .
H16B H 0.8334 0.1257 0.5059 0.076 Uiso 1 1 d R . .


_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 O10 2.366(2) . ?
Tb1 O13 2.391(2) . ?
Tb1 O11 2.390(2) . ?
Tb1 O9 2.397(2) . ?
Tb1 O1 2.4332(19) . ?
Tb1 O6 2.4343(19) . ?
Tb1 O12 2.470(2) . ?
Tb1 O5 2.5317(19) . ?
Tb1 O2 2.5532(19) . ?
Tb1 H9B 2.5577 . ?
O1 C5 1.260(3) . ?
O2 C5 1.258(3) . ?
O3 C1 1.238(4) . ?
O4 C1 1.238(4) . ?
O5 C10 1.253(3) . ?
O6 C10 1.264(3) . ?
O7 C9 1.251(3) . ?
O8 C9 1.254(3) . ?
O9 H9A 0.8200 . ?
O9 H9B 0.9628 . ?
O10 H10A 0.8200 . ?
O10 H10B 0.6679 . ?
O11 H11A 0.8200 . ?
O11 H11B 0.8006 . ?
O12 H12A 0.8199 . ?
O12 H12B 0.8227 . ?
O13 H13A 0.8199 . ?
O13 H13B 0.8543 . ?
C1 C2 1.514(4) . ?
C2 C4 1.391(4) 3_667 ?
C2 C3 1.399(4) . ?
C3 C4 1.386(4) . ?
C3 C5 1.504(4) . ?
C4 C2 1.391(4) 3_667 ?
C4 H4 0.9300 . ?
C6 C8 1.389(4) 3_566 ?
C6 C7 1.391(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.396(4) . ?
C7 C10 1.503(4) . ?
C8 C6 1.389(4) 3_566 ?
C8 C9 1.515(4) . ?
N1 C13 1.331(5) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 C11 1.326(6) . ?
N2 C15 1.333(6) . ?
N2 H2B 0.8600 . ?
C11 C12 1.360(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.406(5) . ?
C14 C15 1.345(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
O14 H14A 0.8777 . ?
O14 H14B 0.7303 . ?
O15 H15A 0.8633 . ?
O15 H15B 0.8547 . ?
O16 H16A 0.8553 . ?
O16 H16B 0.8867 . ?

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
O10 Tb1 O13 137.12(8) . . ?
O10 Tb1 O11 93.48(8) . . ?
O13 Tb1 O11 80.59(8) . . ?
O10 Tb1 O9 77.67(8) . . ?
O13 Tb1 O9 92.26(8) . . ?
O11 Tb1 O9 158.13(9) . . ?
O10 Tb1 O1 76.96(7) . . ?
O13 Tb1 O1 142.14(7) . . ?
O11 Tb1 O1 119.76(7) . . ?
O9 Tb1 O1 78.12(7) . . ?
O10 Tb1 O6 143.81(7) . . ?
O13 Tb1 O6 76.55(7) . . ?
O11 Tb1 O6 77.42(7) . . ?
O9 Tb1 O6 121.22(7) . . ?
O1 Tb1 O6 77.61(8) . . ?
O10 Tb1 O12 68.98(7) . . ?
O13 Tb1 O12 68.21(7) . . ?
O11 Tb1 O12 78.55(7) . . ?
O9 Tb1 O12 79.61(8) . . ?
O1 Tb1 O12 142.46(7) . . ?
O6 Tb1 O12 139.92(7) . . ?
O10 Tb1 O5 139.32(7) . . ?
O13 Tb1 O5 69.19(7) . . ?
O11 Tb1 O5 125.23(7) . . ?
O9 Tb1 O5 69.72(7) . . ?
O1 Tb1 O5 73.15(7) . . ?
O6 Tb1 O5 52.19(6) . . ?
O12 Tb1 O5 125.48(6) . . ?
O10 Tb1 O2 69.90(7) . . ?
O13 Tb1 O2 141.21(7) . . ?
O11 Tb1 O2 68.65(6) . . ?
O9 Tb1 O2 124.71(7) . . ?
O1 Tb1 O2 52.04(6) . . ?
O6 Tb1 O2 74.21(6) . . ?
O12 Tb1 O2 124.62(6) . . ?
O5 Tb1 O2 109.89(7) . . ?
O10 Tb1 H9B 61.9 . . ?
O13 Tb1 H9B 114.4 . . ?
O11 Tb1 H9B 155.1 . . ?
O9 Tb1 H9B 22.1 . . ?
O1 Tb1 H9B 61.1 . . ?
O6 Tb1 H9B 124.2 . . ?
O12 Tb1 H9B 88.5 . . ?
O5 Tb1 H9B 79.6 . . ?
O2 Tb1 H9B 103.1 . . ?
C5 O1 Tb1 96.20(16) . . ?
C5 O2 Tb1 90.60(15) . . ?
C10 O5 Tb1 91.34(16) . . ?
C10 O6 Tb1 95.63(16) . . ?
Tb1 O9 H9A 109.3 . . ?
Tb1 O9 H9B 88.4 . . ?
H9A O9 H9B 65.7 . . ?
Tb1 O10 H10A 109.8 . . ?
Tb1 O10 H10B 115.8 . . ?
H10A O10 H10B 134.4 . . ?
Tb1 O11 H11A 109.5 . . ?
Tb1 O11 H11B 135.3 . . ?
H11A O11 H11B 77.4 . . ?
Tb1 O12 H12A 109.7 . . ?
Tb1 O12 H12B 124.0 . . ?
H12A O12 H12B 125.1 . . ?
Tb1 O13 H13A 109.4 . . ?
Tb1 O13 H13B 108.1 . . ?
H13A O13 H13B 94.3 . . ?
O3 C1 O4 123.4(3) . . ?
O3 C1 C2 119.0(3) . . ?
O4 C1 C2 117.5(3) . . ?
C4 C2 C3 118.5(2) 3_667 . ?
C4 C2 C1 117.8(2) 3_667 . ?
C3 C2 C1 123.7(2) . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 C5 117.1(2) . . ?
C2 C3 C5 123.0(2) . . ?
C3 C4 C2 121.8(2) . 3_667 ?
C3 C4 H4 119.1 . . ?
C2 C4 H4 119.1 3_667 . ?
O2 C5 O1 120.9(2) . . ?
O2 C5 C3 120.2(2) . . ?
O1 C5 C3 118.9(2) . . ?
C8 C6 C7 121.9(2) 3_566 . ?
C8 C6 H6 119.0 3_566 . ?
C7 C6 H6 119.0 . . ?
C6 C7 C8 119.6(2) . . ?
C6 C7 C10 117.6(2) . . ?
C8 C7 C10 122.7(2) . . ?
C6 C8 C7 118.5(2) 3_566 . ?
C6 C8 C9 118.0(2) 3_566 . ?
C7 C8 C9 123.3(2) . . ?
O7 C9 O8 124.1(3) . . ?
O7 C9 C8 118.0(2) . . ?
O8 C9 C8 117.7(2) . . ?
O5 C10 O6 120.6(2) . . ?
O5 C10 C7 120.5(2) . . ?
O6 C10 C7 118.8(2) . . ?
C13 N1 H1A 120.0 . . ?
C13 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C11 N2 C15 120.0(4) . . ?
C11 N2 H2B 120.0 . . ?
C15 N2 H2B 119.9 . . ?
N2 C11 C12 121.2(4) . . ?
N2 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 119.7(4) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
N1 C13 C12 120.8(4) . . ?
N1 C13 C14 121.3(4) . . ?
C12 C13 C14 117.9(4) . . ?
C15 C14 C13 118.5(4) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
N2 C15 C14 122.6(4) . . ?
N2 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
H14A O14 H14B 111.6 . . ?
H15A O15 H15B 118.9 . . ?
H16A O16 H16B 122.9 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.15
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.099
_refine_diff_density_min         -0.963
_refine_diff_density_rms         0.106
