# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_3657
_database_code_depnum_ccdc_archive 'CCDC 1056824'
_audit_update_record             
;
2015-03-30 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 N2 O12 Tb'
_chemical_formula_weight         637.28

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'
O O 0.0492 0.0322 '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'
Tb Tb -9.1472 9.1891 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   R-3

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   29.4783(15)
_cell_length_b                   29.4783(15)
_cell_length_c                   14.1301(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     10633.6(9)
_cell_formula_units_Z            18
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3247
_cell_measurement_theta_min      2.9957
_cell_measurement_theta_max      71.3458

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             5634
_exptl_absorpt_coefficient_mu    15.320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3393
_exptl_absorpt_correction_T_max  0.4135
_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         'fine-focus sealed tube'
_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            21999
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_sigmaI/netI    0.0542
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         67.23
_reflns_number_total             4235
_reflns_number_gt                3327
_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)+(0.0343P)²+12.5548P] 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         4235
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Tb1 Tb 0.674549(12) 0.675725(11) 0.57376(2) 0.03837(11) Uani 1 1 d . . .
N1 N 0.98246(15) 1.03520(15) 0.3743(3) 0.0397(10) Uani 1 1 d . . .
N2 N 0.38522(16) 0.67991(16) 0.5485(3) 0.0429(11) Uani 1 1 d . . .
O1 O 0.58623(14) 0.63491(14) 0.6366(2) 0.0451(9) Uani 1 1 d . . .
O2 O 0.60065(14) 0.68509(15) 0.5133(3) 0.0511(10) Uani 1 1 d . . .
O3 O 0.35586(14) 0.59163(14) 0.5505(3) 0.0533(10) Uani 1 1 d . . .
O4 O 0.63093(14) 0.61366(15) 0.4581(3) 0.0547(11) Uani 1 1 d . . .
O5 O 0.58639(15) 0.59668(16) 0.3253(3) 0.0600(11) Uani 1 1 d . . .
O6 O 0.71530(16) 0.74415(14) 0.4720(3) 0.0577(11) Uani 1 1 d . . .
O7 O 0.72788(15) 0.73042(15) 0.3219(3) 0.0549(10) Uani 1 1 d . . .
O8 O 0.90057(13) 0.96960(13) 0.3747(3) 0.0498(10) Uani 1 1 d . . .
O9 O 0.75752(15) 0.71934(16) 0.6565(3) 0.0626(11) Uani 1 1 d . . .
H9A H 0.7799 0.7150 0.6259 0.094 Uiso 1 1 d R . .
H9C H 0.7536 0.7061 0.7115 0.094 Uiso 1 1 d R . .
O10 O 0.73598(16) 0.65514(17) 0.4861(3) 0.0644(12) Uani 1 1 d . . .
H10A H 0.7660 0.6713 0.5119 0.097 Uiso 1 1 d R . .
H10C H 0.7383 0.6650 0.4289 0.097 Uiso 1 1 d R . .
O11 O 0.6463(5) 0.8073(4) 0.5159(6) 0.217(5) Uani 1 1 d . . .
H11C H 0.6575 0.7971 0.5620 0.260 Uiso 1 1 d R . .
H11A H 0.6137 0.7865 0.5073 0.260 Uiso 1 1 d R . .
O12 O 0.7063(7) 0.8666(8) 0.3885(19) 0.58(3) Uani 1 1 d . . .
H12D H 0.6851 0.8501 0.4333 0.694 Uiso 1 1 d R . .
H12A H 0.7366 0.8714 0.4012 0.694 Uiso 1 1 d R . .
C1 C 0.5690(2) 0.6525(2) 0.5728(4) 0.0449(13) Uani 1 1 d . . .
C2 C 0.5125(2) 0.6341(2) 0.5660(4) 0.0427(12) Uani 1 1 d . . .
C3 C 0.4920(2) 0.6404(2) 0.4825(4) 0.0544(15) Uani 1 1 d . . .
H3 H 0.5137 0.6553 0.4303 0.065 Uiso 1 1 calc R . .
C4 C 0.4398(2) 0.6249(2) 0.4762(4) 0.0554(15) Uani 1 1 d . . .
H4 H 0.4256 0.6278 0.4193 0.067 Uiso 1 1 calc R . .
C5 C 0.4090(2) 0.6051(2) 0.5547(4) 0.0486(14) Uani 1 1 d . . .
C6 C 0.4276(2) 0.5968(2) 0.6375(4) 0.0554(15) Uani 1 1 d . . .
H6 H 0.4055 0.5819 0.6892 0.066 Uiso 1 1 calc R . .
C7 C 0.4795(2) 0.6109(2) 0.6429(4) 0.0538(15) Uani 1 1 d . . .
H7 H 0.4926 0.6050 0.6984 0.065 Uiso 1 1 calc R . .
C8 C 0.3456(2) 0.6312(2) 0.5492(4) 0.0425(13) Uani 1 1 d . . .
C10 C 0.5903(2) 0.5866(2) 0.4099(4) 0.0431(13) Uani 1 1 d . . .
C11 C 0.5436(2) 0.54150(19) 0.4570(4) 0.0408(12) Uani 1 1 d . . .
C12 C 0.4939(2) 0.5206(2) 0.4164(4) 0.0478(14) Uani 1 1 d . . .
H12 H 0.4896 0.5343 0.3599 0.057 Uiso 1 1 calc R . .
C13 C 0.4511(2) 0.4797(2) 0.4599(4) 0.0467(13) Uani 1 1 d . . .
H13 H 0.4181 0.4663 0.4327 0.056 Uiso 1 1 calc R . .
C14 C 0.7389(2) 0.7584(2) 0.3950(4) 0.0442(13) Uani 1 1 d . . .
C15 C 0.78346(19) 0.81343(19) 0.3883(4) 0.0396(12) Uani 1 1 d . . .
C16 C 0.8025(2) 0.8437(2) 0.4705(4) 0.0546(15) Uani 1 1 d . . .
H16 H 0.7881 0.8290 0.5289 0.066 Uiso 1 1 calc R . .
C17 C 0.8422(2) 0.8948(2) 0.4658(4) 0.0551(15) Uani 1 1 d . . .
H17 H 0.8550 0.9148 0.5205 0.066 Uiso 1 1 calc R . .
C18 C 0.86250(19) 0.91606(19) 0.3793(4) 0.0445(13) Uani 1 1 d . . .
C19 C 0.8447(2) 0.8879(2) 0.2977(4) 0.0545(15) Uani 1 1 d . . .
H19 H 0.8587 0.9032 0.2395 0.065 Uiso 1 1 calc R . .
C20 C 0.8054(2) 0.8363(2) 0.3033(4) 0.0516(15) Uani 1 1 d . . .
H20 H 0.7935 0.8166 0.2482 0.062 Uiso 1 1 calc R . .
C21 C 0.95120(19) 0.98357(19) 0.3748(4) 0.0397(12) 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 O6 2.271(4) . ?
Tb1 O7 2.305(4) 6_565 ?
Tb1 O4 2.306(4) . ?
Tb1 O5 2.388(4) 6_565 ?
Tb1 O9 2.421(4) . ?
Tb1 O1 2.425(4) . ?
Tb1 O2 2.481(4) . ?
Tb1 O10 2.506(4) . ?
Tb1 C1 2.832(5) . ?
N1 C21 1.317(6) 3_675 ?
N1 C21 1.328(6) . ?
N2 C8 1.323(6) . ?
N2 C8 1.327(6) 2_665 ?
O1 C1 1.267(6) . ?
O2 C1 1.266(6) . ?
O3 C8 1.342(6) . ?
O3 C5 1.413(6) . ?
O4 C10 1.257(6) . ?
O5 C10 1.252(6) . ?
O5 Tb1 2.388(4) 8_654 ?
O6 C14 1.245(6) . ?
O7 C14 1.258(6) . ?
O7 Tb1 2.305(4) 8_654 ?
O8 C21 1.335(6) . ?
O8 C18 1.408(6) . ?
C1 C2 1.474(7) . ?
C2 C3 1.379(7) . ?
C2 C7 1.390(7) . ?
C3 C4 1.371(8) . ?
C4 C5 1.366(8) . ?
C5 C6 1.364(8) . ?
C6 C7 1.372(8) . ?
C8 N2 1.327(6) 3_565 ?
C10 C11 1.508(7) . ?
C11 C13 1.376(7) 10_666 ?
C11 C12 1.397(7) . ?
C12 C13 1.378(7) . ?
C13 C11 1.376(7) 10_666 ?
C14 C15 1.496(7) . ?
C15 C20 1.371(7) . ?
C15 C16 1.399(7) . ?
C16 C17 1.372(8) . ?
C17 C18 1.367(8) . ?
C18 C19 1.363(8) . ?
C19 C20 1.377(7) . ?
C21 N1 1.317(6) 2_765 ?

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
O6 Tb1 O7 151.95(15) . 6_565 ?
O6 Tb1 O4 95.35(14) . . ?
O7 Tb1 O4 83.14(15) 6_565 . ?
O6 Tb1 O5 76.53(15) . 6_565 ?
O7 Tb1 O5 119.86(14) 6_565 6_565 ?
O4 Tb1 O5 144.39(15) . 6_565 ?
O6 Tb1 O9 83.63(15) . . ?
O7 Tb1 O9 80.38(15) 6_565 . ?
O4 Tb1 O9 141.10(14) . . ?
O5 Tb1 O9 73.29(15) 6_565 . ?
O6 Tb1 O1 129.23(14) . . ?
O7 Tb1 O1 78.30(13) 6_565 . ?
O4 Tb1 O1 80.31(13) . . ?
O5 Tb1 O1 78.74(13) 6_565 . ?
O9 Tb1 O1 129.46(13) . . ?
O6 Tb1 O2 77.69(14) . . ?
O7 Tb1 O2 127.07(13) 6_565 . ?
O4 Tb1 O2 70.84(14) . . ?
O5 Tb1 O2 73.55(14) 6_565 . ?
O9 Tb1 O2 144.86(14) . . ?
O1 Tb1 O2 52.91(12) . . ?
O6 Tb1 O10 77.10(15) . . ?
O7 Tb1 O10 76.25(15) 6_565 . ?
O4 Tb1 O10 68.98(13) . . ?
O5 Tb1 O10 138.91(14) 6_565 . ?
O9 Tb1 O10 72.95(13) . . ?
O1 Tb1 O10 141.93(13) . . ?
O2 Tb1 O10 129.62(13) . . ?
O6 Tb1 C1 103.92(16) . . ?
O7 Tb1 C1 102.26(15) 6_565 . ?
O4 Tb1 C1 72.28(15) . . ?
O5 Tb1 C1 76.16(15) 6_565 . ?
O9 Tb1 C1 145.79(15) . . ?
O1 Tb1 C1 26.48(13) . . ?
O2 Tb1 C1 26.53(13) . . ?
O10 Tb1 C1 141.14(15) . . ?
C21 N1 C21 112.2(5) 3_675 . ?
C8 N2 C8 111.8(5) . 2_665 ?
C1 O1 Tb1 95.0(3) . . ?
C1 O2 Tb1 92.4(3) . . ?
C8 O3 C5 117.1(4) . . ?
C10 O4 Tb1 149.8(4) . . ?
C10 O5 Tb1 122.4(3) . 8_654 ?
C14 O6 Tb1 144.1(4) . . ?
C14 O7 Tb1 141.6(4) . 8_654 ?
C21 O8 C18 119.2(4) . . ?
O2 C1 O1 119.3(5) . . ?
O2 C1 C2 120.3(5) . . ?
O1 C1 C2 120.4(5) . . ?
O2 C1 Tb1 61.1(3) . . ?
O1 C1 Tb1 58.6(3) . . ?
C2 C1 Tb1 172.6(4) . . ?
C3 C2 C7 119.2(5) . . ?
C3 C2 C1 119.7(5) . . ?
C7 C2 C1 121.0(5) . . ?
C4 C3 C2 120.3(6) . . ?
C5 C4 C3 119.0(6) . . ?
C6 C5 C4 122.2(5) . . ?
C6 C5 O3 118.3(5) . . ?
C4 C5 O3 119.5(5) . . ?
C5 C6 C7 118.7(6) . . ?
C6 C7 C2 120.4(5) . . ?
N2 C8 N2 128.2(5) . 3_565 ?
N2 C8 O3 118.9(5) . . ?
N2 C8 O3 112.9(5) 3_565 . ?
O5 C10 O4 122.5(5) . . ?
O5 C10 C11 118.7(5) . . ?
O4 C10 C11 118.8(5) . . ?
C13 C11 C12 118.9(5) 10_666 . ?
C13 C11 C10 121.0(5) 10_666 . ?
C12 C11 C10 120.1(5) . . ?
C13 C12 C11 120.1(5) . . ?
C11 C13 C12 121.0(5) 10_666 . ?
O6 C14 O7 125.4(5) . . ?
O6 C14 C15 117.4(5) . . ?
O7 C14 C15 117.3(5) . . ?
C20 C15 C16 118.2(5) . . ?
C20 C15 C14 122.1(5) . . ?
C16 C15 C14 119.6(5) . . ?
C17 C16 C15 120.7(5) . . ?
C18 C17 C16 119.0(5) . . ?
C19 C18 C17 122.0(5) . . ?
C19 C18 O8 119.5(5) . . ?
C17 C18 O8 118.4(5) . . ?
C18 C19 C20 118.6(5) . . ?
C15 C20 C19 121.5(5) . . ?
N1 C21 N1 127.8(5) 2_765 . ?
N1 C21 O8 119.8(4) 2_765 . ?
N1 C21 O8 112.4(4) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.23
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.054
_refine_diff_density_min         -0.813
_refine_diff_density_rms         0.083
