# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_exp_7192
_database_code_depnum_ccdc_archive 'CCDC 1524904'
_audit_update_record             
;
2016-12-29 deposited with the CCDC.	2019-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N O9 Tb'
_chemical_formula_weight         496.16

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0410(4)
_cell_length_b                   10.1090(8)
_cell_length_c                   15.3272(9)
_cell_angle_alpha                107.510(6)
_cell_angle_beta                 90.986(5)
_cell_angle_gamma                106.051(7)
_cell_volume                     852.67(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2778
_cell_measurement_theta_min      4.7880
_cell_measurement_theta_max      71.2620

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.932
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             478
_exptl_absorpt_coefficient_mu    20.846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2863
_exptl_absorpt_correction_T_max  0.3232
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5016
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0741
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         67.22
_reflns_number_total             3056
_reflns_number_gt                2721
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0939P)²+1.0636P] 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       ?
_refine_ls_number_reflns         3056
_refine_ls_number_parameters     290
_refine_ls_number_restraints     1032
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1529
_refine_ls_wR_factor_gt          0.1465
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      0.944
_refine_ls_shift/su_max          0.000
_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 1.18847(7) 0.22231(4) 0.03673(3) 0.02111(17) Uani 1 1 d U . .
N1 N 0.814(5) 0.3867(19) 0.7312(10) 0.082(4) Uani 0.449(7) 1 d PDU A 1
N1' N 0.929(3) 0.206(2) 0.6728(9) 0.086(3) Uani 0.551(7) 1 d PDU A 2
O1 O 0.9095(9) 0.0411(6) 0.0788(4) 0.0295(11) Uani 1 1 d U . .
O2 O 0.6559(10) -0.1347(6) 0.1080(4) 0.0304(11) Uani 1 1 d U . .
O3 O 0.4460(9) 0.1087(5) 0.0929(3) 0.0260(10) Uani 1 1 d U . .
O4 O 0.3447(11) 0.2792(6) 0.1968(4) 0.0352(12) Uani 1 1 d U . .
O5 O 0.777(4) 0.363(2) 0.4940(11) 0.071(3) Uani 0.449(7) 1 d PU A 1
O5' O 1.098(3) 0.1769(19) 0.4440(10) 0.075(3) Uani 0.551(7) 1 d PU A 2
O6 O 1.5713(10) 0.3942(6) 0.0599(4) 0.0352(13) Uani 1 1 d U . .
O7 O 1.7877(9) 0.5950(6) 0.0378(4) 0.0329(12) Uani 1 1 d U . .
O8 O 0.8400(10) 0.1716(6) -0.0587(4) 0.0356(13) Uani 1 1 d U . .
H8A H 0.7364 0.1025 -0.0492 0.053 Uiso 1 1 d R . .
H8B H 0.7943 0.2469 -0.0459 0.053 Uiso 1 1 d R . .
O9 O 1.0041(11) 0.3867(7) 0.1294(4) 0.0409(14) Uani 1 1 d U . .
H9A H 0.8622 0.3421 0.1290 0.061 Uiso 1 1 d R . .
H9B H 1.0698 0.4198 0.1843 0.061 Uiso 1 1 d R . .
C1 C 0.7725(13) -0.0030(8) 0.1328(5) 0.0249(14) Uani 1 1 d U . .
C2 C 0.7649(16) 0.0935(9) 0.2257(5) 0.0339(16) Uani 1 1 d U A .
C3 C 0.6140(15) 0.1823(9) 0.2476(5) 0.0318(15) Uani 1 1 d U . .
C4 C 0.6215(19) 0.2640(11) 0.3384(6) 0.0450(18) Uani 1 1 d U A .
H4 H 0.5201 0.3198 0.3537 0.054 Uiso 1 1 calc R . .
C5 C 0.773(2) 0.2661(13) 0.4072(6) 0.056(2) Uani 1 1 d U . .
H5 H 0.7769 0.3240 0.4676 0.068 Uiso 0.551(7) 1 d PR A 2
C6 C 0.918(2) 0.1803(14) 0.3848(7) 0.060(2) Uani 1 1 d U A .
H6 H 1.0180 0.1782 0.4307 0.072 Uiso 0.449(7) 1 d PR A 1
C7 C 0.9163(19) 0.0974(12) 0.2950(6) 0.0486(19) Uani 1 1 d U . .
H7 H 1.0200 0.0430 0.2811 0.058 Uiso 1 1 calc R A .
C8 C 0.4583(14) 0.1901(8) 0.1749(5) 0.0273(14) Uani 1 1 d U . .
C9 C 0.745(6) 0.311(2) 0.5673(10) 0.075(3) Uani 0.449(7) 1 d PDU A 1
C10 C 0.808(5) 0.4212(17) 0.6507(12) 0.081(4) Uani 0.449(7) 1 d PDU A 1
H10 H 0.8461 0.5177 0.6526 0.097 Uiso 0.449(7) 1 calc PR A 1
C11 C 0.711(6) 0.246(2) 0.7296(10) 0.083(4) Uani 0.449(7) 1 d PDU A 1
H11 H 0.6758 0.2252 0.7839 0.099 Uiso 0.449(7) 1 calc PR A 1
C12 C 0.661(6) 0.1347(17) 0.6461(13) 0.081(4) Uani 0.449(7) 1 d PDU A 1
H12 H 0.6338 0.0387 0.6443 0.097 Uiso 0.449(7) 1 calc PR A 1
C13 C 0.652(5) 0.1688(19) 0.5654(10) 0.080(4) Uani 0.449(7) 1 d PDU A 1
H13 H 0.5849 0.0966 0.5103 0.096 Uiso 0.449(7) 1 calc PR A 1
C14 C 1.6043(14) 0.4966(8) 0.0281(5) 0.0278(16) Uani 1 1 d U . .
C9' C 1.093(3) 0.224(2) 0.5346(7) 0.071(3) Uani 0.551(7) 1 d PDU A 2
C10' C 0.914(3) 0.162(2) 0.5779(9) 0.078(3) Uani 0.551(7) 1 d PDU A 2
H10' H 0.7829 0.0916 0.5432 0.094 Uiso 0.551(7) 1 calc PR A 2
C11' C 1.123(3) 0.311(2) 0.7236(8) 0.079(4) Uani 0.551(7) 1 d PDU A 2
H11' H 1.1336 0.3410 0.7876 0.095 Uiso 0.551(7) 1 calc PR A 2
C12' C 1.302(3) 0.373(2) 0.6804(10) 0.085(4) Uani 0.551(7) 1 d PDU A 2
H12' H 1.4312 0.4460 0.7151 0.102 Uiso 0.551(7) 1 calc PR A 2
C13' C 1.288(3) 0.328(3) 0.5857(10) 0.082(4) Uani 0.551(7) 1 d PDU A 2
H13' H 1.4111 0.3670 0.5563 0.099 Uiso 0.551(7) 1 calc PR A 2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O1 2.378(5) . ?
Tb1 O9 2.383(6) . ?
Tb1 O8 2.383(5) . ?
Tb1 O7 2.422(5) 2_865 ?
Tb1 O6 2.423(5) . ?
Tb1 O2 2.437(5) 2_755 ?
Tb1 O4 2.453(5) 1_655 ?
Tb1 O3 2.453(5) 1_655 ?
Tb1 O1 2.613(5) 2_755 ?
Tb1 C8 2.800(7) 1_655 ?
Tb1 C1 2.927(7) 2_755 ?
N1 C10 1.382(8) . ?
N1 C11 1.382(8) . ?
N1' C11' 1.378(8) . ?
N1' C10' 1.381(8) . ?
O1 C1 1.269(9) . ?
O1 Tb1 2.613(5) 2_755 ?
O2 C1 1.258(9) . ?
O2 Tb1 2.437(5) 2_755 ?
O3 C8 1.267(9) . ?
O3 Tb1 2.453(5) 1_455 ?
O4 C8 1.250(9) . ?
O4 Tb1 2.453(5) 1_455 ?
O5 C9 1.37(2) . ?
O5 C5 1.39(2) . ?
O5' C9' 1.329(18) . ?
O5' C6 1.419(18) . ?
O6 C14 1.242(9) . ?
O7 C14 1.238(10) . ?
O7 Tb1 2.422(5) 2_865 ?
C1 C2 1.474(10) . ?
C1 Tb1 2.927(7) 2_755 ?
C2 C7 1.374(12) . ?
C2 C3 1.425(12) . ?
C3 C4 1.382(12) . ?
C3 C8 1.479(10) . ?
C4 C5 1.374(14) . ?
C5 C6 1.373(16) . ?
C6 C7 1.378(14) . ?
C8 Tb1 2.800(7) 1_455 ?
C9 C10 1.382(8) . ?
C9 C13 1.382(8) . ?
C11 C12 1.386(8) . ?
C12 C13 1.384(8) . ?
C14 C14 1.543(14) 2_865 ?
C9' C10' 1.376(8) . ?
C9' C13' 1.380(8) . ?
C11' C12' 1.377(8) . ?
C12' C13' 1.378(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Tb1 O9 85.2(2) . . ?
O1 Tb1 O8 74.50(18) . . ?
O9 Tb1 O8 77.8(2) . . ?
O1 Tb1 O7 140.64(18) . 2_865 ?
O9 Tb1 O7 74.5(2) . 2_865 ?
O8 Tb1 O7 68.51(18) . 2_865 ?
O1 Tb1 O6 150.78(18) . . ?
O9 Tb1 O6 96.8(2) . . ?
O8 Tb1 O6 134.52(18) . . ?
O7 Tb1 O6 66.59(17) 2_865 . ?
O1 Tb1 O2 115.06(17) . 2_755 ?
O9 Tb1 O2 148.53(19) . 2_755 ?
O8 Tb1 O2 84.6(2) . 2_755 ?
O7 Tb1 O2 74.85(19) 2_865 2_755 ?
O6 Tb1 O2 77.3(2) . 2_755 ?
O1 Tb1 O4 80.28(19) . 1_655 ?
O9 Tb1 O4 73.22(19) . 1_655 ?
O8 Tb1 O4 142.8(2) . 1_655 ?
O7 Tb1 O4 123.33(19) 2_865 1_655 ?
O6 Tb1 O4 72.5(2) . 1_655 ?
O2 Tb1 O4 131.38(19) 2_755 1_655 ?
O1 Tb1 O3 80.18(18) . 1_655 ?
O9 Tb1 O3 126.14(18) . 1_655 ?
O8 Tb1 O3 143.42(18) . 1_655 ?
O7 Tb1 O3 138.86(18) 2_865 1_655 ?
O6 Tb1 O3 75.15(17) . 1_655 ?
O2 Tb1 O3 82.72(17) 2_755 1_655 ?
O4 Tb1 O3 53.35(17) 1_655 1_655 ?
O1 Tb1 O1 64.4(2) . 2_755 ?
O9 Tb1 O1 140.8(2) . 2_755 ?
O8 Tb1 O1 70.85(18) . 2_755 ?
O7 Tb1 O1 113.37(17) 2_865 2_755 ?
O6 Tb1 O1 121.96(19) . 2_755 ?
O2 Tb1 O1 50.71(17) 2_755 2_755 ?
O4 Tb1 O1 121.20(17) 1_655 2_755 ?
O3 Tb1 O1 74.57(16) 1_655 2_755 ?
O1 Tb1 C8 79.9(2) . 1_655 ?
O9 Tb1 C8 99.6(2) . 1_655 ?
O8 Tb1 C8 154.4(2) . 1_655 ?
O7 Tb1 C8 135.9(2) 2_865 1_655 ?
O6 Tb1 C8 71.0(2) . 1_655 ?
O2 Tb1 C8 107.2(2) 2_755 1_655 ?
O4 Tb1 C8 26.5(2) 1_655 1_655 ?
O3 Tb1 C8 26.88(19) 1_655 1_655 ?
O1 Tb1 C8 98.70(18) 2_755 1_655 ?
O1 Tb1 C1 90.03(19) . 2_755 ?
O9 Tb1 C1 153.5(2) . 2_755 ?
O8 Tb1 C1 75.7(2) . 2_755 ?
O7 Tb1 C1 93.49(19) 2_865 2_755 ?
O6 Tb1 C1 100.0(2) . 2_755 ?
O2 Tb1 C1 25.05(19) 2_755 2_755 ?
O4 Tb1 C1 131.63(19) 1_655 2_755 ?
O3 Tb1 C1 78.35(18) 1_655 2_755 ?
O1 Tb1 C1 25.69(19) 2_755 2_755 ?
C8 Tb1 C1 105.2(2) 1_655 2_755 ?
C10 N1 C11 119.5(8) . . ?
C11' N1' C10' 119.6(7) . . ?
C1 O1 Tb1 153.2(5) . . ?
C1 O1 Tb1 91.1(4) . 2_755 ?
Tb1 O1 Tb1 115.6(2) . 2_755 ?
C1 O2 Tb1 99.8(4) . 2_755 ?
C8 O3 Tb1 92.0(4) . 1_455 ?
C8 O4 Tb1 92.4(4) . 1_455 ?
C9 O5 C5 119.0(18) . . ?
C9' O5' C6 119.5(17) . . ?
C14 O6 Tb1 119.7(5) . . ?
C14 O7 Tb1 120.0(5) . 2_865 ?
O2 C1 O1 118.3(7) . . ?
O2 C1 C2 120.3(7) . . ?
O1 C1 C2 121.2(7) . . ?
O2 C1 Tb1 55.2(4) . 2_755 ?
O1 C1 Tb1 63.2(4) . 2_755 ?
C2 C1 Tb1 171.0(5) . 2_755 ?
C7 C2 C3 118.6(8) . . ?
C7 C2 C1 116.8(8) . . ?
C3 C2 C1 124.5(7) . . ?
C4 C3 C2 118.1(8) . . ?
C4 C3 C8 120.8(8) . . ?
C2 C3 C8 121.1(7) . . ?
C5 C4 C3 122.6(9) . . ?
C6 C5 C4 118.5(9) . . ?
C6 C5 O5 124.7(12) . . ?
C4 C5 O5 116.8(12) . . ?
C5 C6 C7 120.8(10) . . ?
C5 C6 O5' 126.7(11) . . ?
C7 C6 O5' 112.1(11) . . ?
C2 C7 C6 121.3(10) . . ?
O4 C8 O3 122.1(7) . . ?
O4 C8 C3 118.3(7) . . ?
O3 C8 C3 119.6(7) . . ?
O4 C8 Tb1 61.1(4) . 1_455 ?
O3 C8 Tb1 61.1(4) . 1_455 ?
C3 C8 Tb1 175.9(6) . 1_455 ?
O5 C9 C10 112.3(15) . . ?
O5 C9 C13 127.7(15) . . ?
C10 C9 C13 119.9(7) . . ?
N1 C10 C9 119.5(7) . . ?
N1 C11 C12 119.2(8) . . ?
C13 C12 C11 119.1(8) . . ?
C9 C13 C12 119.5(7) . . ?
O7 C14 O6 126.5(7) . . ?
O7 C14 C14 116.6(8) . 2_865 ?
O6 C14 C14 116.9(8) . 2_865 ?
O5' C9' C10' 122.6(14) . . ?
O5' C9' C13' 116.7(14) . . ?
C10' C9' C13' 120.3(7) . . ?
C9' C10' N1' 120.0(7) . . ?
C12' C11' N1' 120.5(7) . . ?
C11' C12' C13' 119.8(7) . . ?
C12' C13' C9' 119.8(7) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        67.22
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         3.208
_refine_diff_density_min         -1.361
_refine_diff_density_rms         0.214
