# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1850378'
loop_
_audit_author_name
_audit_author_address
'Xia Wang'
;soochow university
China
;
_audit_update_record             
;
2018-06-19 deposited with the CCDC.	2019-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'compound 1'
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 N2 O7 Tb'
_chemical_formula_sum            'C15 H11 N2 O7 Tb'
_chemical_formula_weight         490.19

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.0348(19)
_cell_length_b                   9.2759(17)
_cell_length_c                   14.386(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.876(5)
_cell_angle_gamma                90
_cell_volume                     1458.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    168(2)
_cell_measurement_reflns_used    3986
_cell_measurement_theta_min      2.332
_cell_measurement_theta_max      24.995

_exptl_crystal_description       BULK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.232
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.030
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    4.894
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_process_details   'SADABS, Bruker'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      168(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'BRUKER apex II'
_diffrn_measurement_method       '0.5 wide w/ exposures'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            19910
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.620
_diffrn_reflns_theta_max         27.550
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3369
_reflns_number_gt                2922
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.999

_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.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0252P)²+1.7081P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3369
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0206
_refine_ls_wR_factor_ref         0.0537
_refine_ls_wR_factor_gt          0.0512
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.003
_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
Tb1 Tb -0.62572(2) -1.24126(2) 1.09089(2) 0.01156(6) Uani 1 1 d . . . . .
O1 O -0.65179(18) -1.0554(2) 0.97731(14) 0.0176(4) Uani 1 1 d . . . . .
O2 O -0.60470(19) -1.3733(2) 0.94703(14) 0.0175(4) Uani 1 1 d . . . . .
O3 O -0.75864(19) -1.1031(2) 1.18139(15) 0.0208(5) Uani 1 1 d . . . . .
O4 O -0.43422(18) -1.1507(2) 1.06129(14) 0.0173(4) Uani 1 1 d . . . . .
O5 O -0.50733(19) -1.5520(2) 0.88337(13) 0.0183(5) Uani 1 1 d . . . . .
O6 O -0.5901(2) -0.9815(2) 1.16810(14) 0.0219(5) Uani 1 1 d . . . . .
O7 O -0.5416(2) -1.2595(2) 1.25535(15) 0.0226(5) Uani 1 1 d . . . . .
H1 H -0.5032 -1.3369 1.2653 0.034 Uiso 1 1 d R U . . .
N1 N -0.8527(2) -1.2467(2) 1.01133(17) 0.0153(5) Uani 1 1 d . . . . .
N2 N -0.7613(2) -1.4338(3) 1.14997(17) 0.0167(5) Uani 1 1 d . . . . .
C1 C -0.5633(3) -0.9727(3) 0.97566(19) 0.0142(6) Uani 1 1 d . . . . .
C2 C -0.5323(3) -1.4786(3) 0.95060(19) 0.0135(6) Uani 1 1 d . . . . .
C3 C -0.7176(3) -1.5265(3) 1.2175(2) 0.0211(7) Uani 1 1 d . . . . .
H3 H -0.6333 -1.5352 1.2327 0.025 Uiso 1 1 calc R U . . .
C4 C -0.9340(3) -1.3225(3) 1.05593(19) 0.0146(6) Uani 1 1 d . . . . .
C5 C -0.6923(3) -0.9925(3) 1.1968(2) 0.0205(7) Uani 1 1 d . . . . .
H4 H -0.6516 -1.0371 1.2563 0.025 Uiso 1 1 d R U . . .
C6 C -1.0957(3) -1.4908(3) 1.1474(2) 0.0222(7) Uani 1 1 d . . . . .
H5 H -1.1490 -1.5478 1.1762 0.027 Uiso 1 1 calc R U . . .
C7 C -1.0616(3) -1.3077(3) 1.0343(2) 0.0171(6) Uani 1 1 d . . . . .
C9 C -0.8851(3) -1.4227(3) 1.1290(2) 0.0147(6) Uani 1 1 d . . . . .
C10 C -0.8990(3) -1.1575(3) 0.9431(2) 0.0184(6) Uani 1 1 d . . . . .
H6 H -0.8451 -1.1085 0.9100 0.022 Uiso 1 1 calc R U . . .
C11 C -1.1412(3) -1.3943(3) 1.0808(2) 0.0203(7) Uani 1 1 d . . . . .
H7 H -1.2254 -1.3847 1.0653 0.024 Uiso 1 1 calc R U . . .
C12 C -1.1054(3) -1.2060(4) 0.9647(2) 0.0229(7) Uani 1 1 d . . . . .
H8 H -1.1888 -1.1887 0.9505 0.027 Uiso 1 1 calc R U . . .
C13 C -0.9667(3) -1.5056(3) 1.1738(2) 0.0186(6) Uani 1 1 d . . . . .
C16 C -0.9166(3) -1.6020(3) 1.2448(2) 0.0217(7) Uani 1 1 d . . . . .
H11 H -0.9677 -1.6583 1.2763 0.026 Uiso 1 1 calc R U . . .
C17 C -0.7932(3) -1.6117(3) 1.2667(2) 0.0224(7) Uani 1 1 d . . . . .
H12 H -0.7589 -1.6740 1.3137 0.027 Uiso 1 1 calc R U . . .
C20 C -1.0246(3) -1.1338(3) 0.9187(2) 0.0231(7) Uani 1 1 d . . . . .
H13 H -1.0526 -1.0689 0.8712 0.028 Uiso 1 1 calc R U . . .
H22 H -0.5827 -1.2188 1.3029 0.028 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
Tb1 O1 2.365(2) . ?
Tb1 O4 2.366(2) . ?
Tb1 O5 2.413(2) 3_427 ?
Tb1 O7 2.426(2) . ?
Tb1 O2 2.443(2) . ?
Tb1 O3 2.452(2) . ?
Tb1 N2 2.549(2) . ?
Tb1 N1 2.608(3) . ?
Tb1 O6 2.659(2) . ?
Tb1 C5 2.914(3) . ?
O1 C1 1.245(3) . ?
O2 C2 1.259(3) . ?
O3 C5 1.262(4) . ?
O4 C1 1.261(3) 3_437 ?
O5 C2 1.244(3) . ?
O5 Tb1 2.413(2) 3_427 ?
O6 C5 1.257(4) . ?
N1 C10 1.330(4) . ?
N1 C4 1.367(4) . ?
N2 C3 1.337(4) . ?
N2 C9 1.362(4) . ?
C1 O4 1.261(3) 3_437 ?
C1 C1 1.559(6) 3_437 ?
C2 C2 1.552(5) 3_427 ?
C3 C17 1.408(4) . ?
C4 C7 1.406(4) . ?
C4 C9 1.451(4) . ?
C6 C11 1.356(5) . ?
C6 C13 1.428(4) . ?
C7 C12 1.412(5) . ?
C7 C11 1.424(4) . ?
C9 C13 1.406(4) . ?
C10 C20 1.400(4) . ?
C12 C20 1.358(5) . ?
C13 C16 1.412(4) . ?
C16 C17 1.359(5) . ?

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 69.14(7) . . ?
O1 Tb1 O5 134.35(7) . 3_427 ?
O4 Tb1 O5 76.72(7) . 3_427 ?
O1 Tb1 O7 135.94(7) . . ?
O4 Tb1 O7 88.20(8) . . ?
O5 Tb1 O7 69.60(7) 3_427 . ?
O1 Tb1 O2 78.27(7) . . ?
O4 Tb1 O2 80.49(7) . . ?
O5 Tb1 O2 66.75(6) 3_427 . ?
O7 Tb1 O2 136.31(7) . . ?
O1 Tb1 O3 87.76(7) . . ?
O4 Tb1 O3 121.59(7) . . ?
O5 Tb1 O3 136.85(7) 3_427 . ?
O7 Tb1 O3 72.27(7) . . ?
O2 Tb1 O3 147.67(7) . . ?
O1 Tb1 N2 136.01(7) . . ?
O4 Tb1 N2 152.64(7) . . ?
O5 Tb1 N2 76.38(8) 3_427 . ?
O7 Tb1 N2 77.85(8) . . ?
O2 Tb1 N2 93.41(8) . . ?
O3 Tb1 N2 76.59(8) . . ?
O1 Tb1 N1 72.08(7) . . ?
O4 Tb1 N1 139.07(7) . . ?
O5 Tb1 N1 125.44(7) 3_427 . ?
O7 Tb1 N1 130.00(8) . . ?
O2 Tb1 N1 79.37(7) . . ?
O3 Tb1 N1 68.57(7) . . ?
N2 Tb1 N1 63.94(8) . . ?
O1 Tb1 O6 68.00(7) . . ?
O4 Tb1 O6 70.68(7) . . ?
O5 Tb1 O6 127.16(7) 3_427 . ?
O7 Tb1 O6 68.96(7) . . ?
O2 Tb1 O6 141.46(7) . . ?
O3 Tb1 O6 50.92(7) . . ?
N2 Tb1 O6 123.73(7) . . ?
N1 Tb1 O6 106.18(7) . . ?
O1 Tb1 C5 76.62(8) . . ?
O4 Tb1 C5 96.22(8) . . ?
O5 Tb1 C5 137.81(8) 3_427 . ?
O7 Tb1 C5 68.64(8) . . ?
O2 Tb1 C5 154.13(8) . . ?
O3 Tb1 C5 25.38(8) . . ?
N2 Tb1 C5 100.30(9) . . ?
N1 Tb1 C5 87.06(8) . . ?
O6 Tb1 C5 25.55(8) . . ?
C1 O1 Tb1 116.16(18) . . ?
C2 O2 Tb1 119.21(18) . . ?
C5 O3 Tb1 98.25(19) . . ?
C1 O4 Tb1 115.46(18) 3_437 . ?
C2 O5 Tb1 120.69(18) . 3_427 ?
C5 O6 Tb1 88.62(18) . . ?
C10 N1 C4 117.1(3) . . ?
C10 N1 Tb1 124.1(2) . . ?
C4 N1 Tb1 117.15(18) . . ?
C3 N2 C9 117.4(3) . . ?
C3 N2 Tb1 121.6(2) . . ?
C9 N2 Tb1 119.33(18) . . ?
O1 C1 O4 126.6(3) . 3_437 ?
O1 C1 C1 116.7(3) . 3_437 ?
O4 C1 C1 116.8(3) 3_437 3_437 ?
O5 C2 O2 126.9(3) . . ?
O5 C2 C2 116.7(3) . 3_427 ?
O2 C2 C2 116.4(3) . 3_427 ?
N2 C3 C17 123.2(3) . . ?
N1 C4 C7 123.2(3) . . ?
N1 C4 C9 117.9(3) . . ?
C7 C4 C9 119.0(3) . . ?
O6 C5 O3 122.2(3) . . ?
O6 C5 Tb1 65.83(16) . . ?
O3 C5 Tb1 56.38(15) . . ?
C11 C6 C13 120.7(3) . . ?
C4 C7 C12 117.2(3) . . ?
C4 C7 C11 120.3(3) . . ?
C12 C7 C11 122.5(3) . . ?
N2 C9 C13 122.9(3) . . ?
N2 C9 C4 118.1(3) . . ?
C13 C9 C4 119.0(3) . . ?
N1 C10 C20 123.4(3) . . ?
C6 C11 C7 120.8(3) . . ?
C20 C12 C7 119.5(3) . . ?
C9 C13 C16 117.8(3) . . ?
C9 C13 C6 120.2(3) . . ?
C16 C13 C6 122.0(3) . . ?
C17 C16 C13 119.4(3) . . ?
C16 C17 C3 119.4(3) . . ?
C12 C20 C10 119.5(3) . . ?

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 O4 -161.5(2) . . . 3_437 ?
Tb1 O1 C1 C1 18.4(4) . . . 3_437 ?
Tb1 O5 C2 O2 -176.3(2) 3_427 . . . ?
Tb1 O5 C2 C2 3.7(4) 3_427 . . 3_427 ?
Tb1 O2 C2 O5 -176.4(2) . . . . ?
Tb1 O2 C2 C2 3.6(4) . . . 3_427 ?
C9 N2 C3 C17 0.1(4) . . . . ?
Tb1 N2 C3 C17 165.2(2) . . . . ?
C10 N1 C4 C7 -1.4(4) . . . . ?
Tb1 N1 C4 C7 164.5(2) . . . . ?
C10 N1 C4 C9 178.6(3) . . . . ?
Tb1 N1 C4 C9 -15.4(3) . . . . ?
Tb1 O6 C5 O3 0.8(3) . . . . ?
Tb1 O3 C5 O6 -0.9(3) . . . . ?
N1 C4 C7 C12 -1.8(4) . . . . ?
C9 C4 C7 C12 178.2(3) . . . . ?
N1 C4 C7 C11 177.4(3) . . . . ?
C9 C4 C7 C11 -2.6(4) . . . . ?
C3 N2 C9 C13 -1.2(4) . . . . ?
Tb1 N2 C9 C13 -166.6(2) . . . . ?
C3 N2 C9 C4 180.0(3) . . . . ?
Tb1 N2 C9 C4 14.6(3) . . . . ?
N1 C4 C9 N2 1.0(4) . . . . ?
C7 C4 C9 N2 -179.0(3) . . . . ?
N1 C4 C9 C13 -177.9(3) . . . . ?
C7 C4 C9 C13 2.2(4) . . . . ?
C4 N1 C10 C20 3.0(4) . . . . ?
Tb1 N1 C10 C20 -161.9(2) . . . . ?
C13 C6 C11 C7 1.2(5) . . . . ?
C4 C7 C11 C6 0.9(4) . . . . ?
C12 C7 C11 C6 -179.9(3) . . . . ?
C4 C7 C12 C20 3.6(5) . . . . ?
C11 C7 C12 C20 -175.6(3) . . . . ?
N2 C9 C13 C16 1.4(4) . . . . ?
C4 C9 C13 C16 -179.9(3) . . . . ?
N2 C9 C13 C6 -178.8(3) . . . . ?
C4 C9 C13 C6 -0.1(4) . . . . ?
C11 C6 C13 C9 -1.7(5) . . . . ?
C11 C6 C13 C16 178.1(3) . . . . ?
C9 C13 C16 C17 -0.4(4) . . . . ?
C6 C13 C16 C17 179.8(3) . . . . ?
C13 C16 C17 C3 -0.6(5) . . . . ?
N2 C3 C17 C16 0.8(5) . . . . ?
C7 C12 C20 C10 -2.2(5) . . . . ?
N1 C10 C20 C12 -1.2(5) . . . . ?

_refine_diff_density_max         0.958
_refine_diff_density_min         -1.042
_refine_diff_density_rms         0.114

_shelxl_version_number           2014-3

