# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 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_EuL
_database_code_depnum_ccdc_archive 'CCDC 1505265'
_audit_update_record             
;
2016-09-20 deposited with the CCDC.
2017-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10.50 H4.50 Eu0.50 N0.50 O5'
_chemical_formula_weight         293.63

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'
Eu Eu -8.9294 11.1857 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   8.5023(2)
_cell_length_b                   17.3319(4)
_cell_length_c                   12.1180(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1785.72(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    3037
_cell_measurement_theta_min      4.4380
_cell_measurement_theta_max      72.7330

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.184
_exptl_crystal_F_000             1140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    25.784
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.60026
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova (Cu) X-ray Source'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            6770
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.452
_diffrn_reflns_theta_max         73.271
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1828
_reflns_number_gt                1577
_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.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1000P)²] 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         1828
_refine_ls_number_parameters     152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.1488
_refine_ls_wR_factor_gt          0.1393
_refine_ls_goodness_of_fit_ref   1.214
_refine_ls_restrained_S_all      1.214
_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_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
EU1 Eu -0.00276(4) 0.250000 0.31883(3) 0.0119(2) Uani 1 2 d S T P . .
O1 O 0.0757(5) 0.250000 0.5216(4) 0.0146(8) Uani 1 2 d S T P . .
O5 O -0.4358(4) -0.11405(17) 0.0730(3) 0.0219(7) Uani 1 1 d . . . . .
O2 O -0.2604(6) 0.250000 0.4121(5) 0.0356(12) Uani 1 2 d S T P . .
N1 N -0.0959(6) 0.250000 -0.0655(4) 0.0124(9) Uani 1 2 d S T P . .
C2 C -0.1798(5) 0.0966(2) 0.0336(4) 0.0151(8) Uani 1 1 d . . . . .
C11 C 0.1838(9) 0.250000 -0.1854(5) 0.0226(14) Uani 1 2 d S T P . .
H11 H 0.280133 0.250000 -0.225102 0.027 Uiso 1 2 calc R U P . .
O4 O -0.0158(4) 0.1677(3) 0.1548(4) 0.0242(9) Uani 1 1 d . . . . .
C5 C -0.3868(6) -0.0946(3) -0.0229(4) 0.0219(10) Uani 1 1 d . . . . .
O6 O -0.4215(5) -0.1293(2) -0.1096(3) 0.0356(10) Uani 1 1 d . . . . .
C8 C -0.1110(5) 0.1100(2) -0.0695(4) 0.0143(8) Uani 1 1 d . . . . .
C7 C -0.1288(6) 0.0558(3) -0.1533(4) 0.0202(9) Uani 1 1 d . . . . .
H7 H -0.080340 0.064408 -0.222876 0.024 Uiso 1 1 calc R U . . .
C10 C 0.1130(5) 0.1810(2) -0.1563(4) 0.0175(9) Uani 1 1 d . . . . .
H10 H 0.159062 0.133141 -0.176667 0.021 Uiso 1 1 calc R U . . .
C9 C -0.0274(5) 0.1831(3) -0.0965(4) 0.0147(9) Uani 1 1 d . . . . .
C1 C -0.1544(5) 0.1496(2) 0.1296(3) 0.0186(9) Uani 1 1 d . . . . .
C4 C -0.2872(6) -0.0237(3) -0.0349(4) 0.0167(10) Uani 1 1 d . . . . .
C6 C -0.2159(5) -0.0101(3) -0.1363(4) 0.0211(10) Uani 1 1 d . . . . .
H6 H -0.227341 -0.046576 -0.194321 0.025 Uiso 1 1 calc R U . . .
C3 C -0.2682(6) 0.0293(3) 0.0496(4) 0.0165(10) Uani 1 1 d . . . . .
H3 H -0.315710 0.019862 0.119270 0.020 Uiso 1 1 calc R U . . .
O3 O -0.2710(4) 0.1716(2) 0.1858(3) 0.0270(8) Uiso 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
EU1 O6 2.355(3) 7_566 ?
EU1 O6 2.355(3) 2_455 ?
EU1 O3 2.394(4) 3 ?
EU1 O3 2.394(4) 6_656 ?
EU1 O4 2.450(5) . ?
EU1 O4 2.450(5) 8_565 ?
EU1 O2 2.465(5) . ?
EU1 O1 2.547(4) . ?
O5 C5 1.279(6) . ?
N1 C9 1.351(6) . ?
N1 C9 1.351(6) 8_565 ?
C2 C8 1.398(6) . ?
C2 C3 1.401(6) . ?
C2 C1 1.499(6) . ?
C11 C10 1.384(6) . ?
C11 C10 1.384(6) 8_565 ?
O4 C1 1.257(6) . ?
C5 O6 1.246(6) . ?
C5 C4 1.499(6) . ?
O6 EU1 2.355(3) 2_454 ?
C8 C7 1.391(6) . ?
C8 C9 1.490(6) . ?
C7 C6 1.377(6) . ?
C10 C9 1.397(6) . ?
C1 O3 1.261(6) . ?
C4 C3 1.385(8) . ?
C4 C6 1.390(7) . ?
O3 EU1 2.394(4) 6_556 ?

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 EU1 O6 125.4(2) 7_566 2_455 ?
O6 EU1 O3 74.31(14) 7_566 3 ?
O6 EU1 O3 137.57(14) 2_455 3 ?
O6 EU1 O3 137.57(14) 7_566 6_656 ?
O6 EU1 O3 74.31(14) 2_455 6_656 ?
O3 EU1 O3 69.14(18) 3 6_656 ?
O6 EU1 O4 143.52(14) 7_566 . ?
O6 EU1 O4 76.63(14) 2_455 . ?
O3 EU1 O4 110.42(12) 3 . ?
O3 EU1 O4 71.80(12) 6_656 . ?
O6 EU1 O4 76.63(14) 7_566 8_565 ?
O6 EU1 O4 143.52(14) 2_455 8_565 ?
O3 EU1 O4 71.80(12) 3 8_565 ?
O3 EU1 O4 110.42(12) 6_656 8_565 ?
O4 EU1 O4 71.3(2) . 8_565 ?
O6 EU1 O2 65.67(11) 7_566 . ?
O6 EU1 O2 65.67(11) 2_455 . ?
O3 EU1 O2 137.92(11) 3 . ?
O3 EU1 O2 137.92(11) 6_656 . ?
O4 EU1 O2 109.38(14) . . ?
O4 EU1 O2 109.38(14) 8_565 . ?
O6 EU1 O1 73.52(10) 7_566 . ?
O6 EU1 O1 73.52(10) 2_455 . ?
O3 EU1 O1 78.87(11) 3 . ?
O3 EU1 O1 78.87(11) 6_656 . ?
O4 EU1 O1 142.66(12) . . ?
O4 EU1 O1 142.66(12) 8_565 . ?
O2 EU1 O1 77.90(16) . . ?
C9 N1 C9 118.3(5) . 8_565 ?
C8 C2 C3 119.1(4) . . ?
C8 C2 C1 122.1(4) . . ?
C3 C2 C1 118.7(4) . . ?
C10 C11 C10 119.5(6) . 8_565 ?
C1 O4 EU1 112.6(3) . . ?
O6 C5 O5 124.1(4) . . ?
O6 C5 C4 116.5(4) . . ?
O5 C5 C4 119.3(4) . . ?
C5 O6 EU1 143.5(3) . 2_454 ?
C7 C8 C2 119.7(4) . . ?
C7 C8 C9 117.7(4) . . ?
C2 C8 C9 122.5(4) . . ?
C6 C7 C8 120.6(4) . . ?
C11 C10 C9 118.8(4) . . ?
N1 C9 C10 122.3(4) . . ?
N1 C9 C8 117.6(4) . . ?
C10 C9 C8 120.0(4) . . ?
O4 C1 O3 122.0(4) . . ?
O4 C1 C2 118.4(4) . . ?
O3 C1 C2 119.4(4) . . ?
C3 C4 C6 119.4(4) . . ?
C3 C4 C5 122.5(5) . . ?
C6 C4 C5 118.1(4) . . ?
C7 C6 C4 120.5(4) . . ?
C4 C3 C2 120.8(5) . . ?
C1 O3 EU1 143.7(3) . 6_556 ?

_refine_diff_density_max         1.505
_refine_diff_density_min         -2.016
_refine_diff_density_rms         0.129



####################################################################### 
# 
# 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_GdL
_database_code_depnum_ccdc_archive 'CCDC 1505266'
_audit_update_record             
;
2016-09-20 deposited with the CCDC.
2017-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H9 Gd N O10'
_chemical_formula_weight         592.54

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'
Gd Gd -8.8380 11.9157 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   8.5011(3)
_cell_length_b                   17.2958(5)
_cell_length_c                   12.0726(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1775.07(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1966
_cell_measurement_theta_min      4.4540
_cell_measurement_theta_max      72.7900

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.217
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    24.812
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.65341
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova (Cu) X-ray Source'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            4320
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.466
_diffrn_reflns_theta_max         73.257
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1792
_reflns_number_gt                1452
_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.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+26.4221P] 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         1792
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1064
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_restrained_S_all      1.157
_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_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
GD1 Gd 0.00404(7) 0.750000 0.81903(4) 0.01344(17) Uani 1 2 d S T P . .
N1 N 0.0960(10) 0.750000 0.4343(6) 0.0148(17) Uani 1 2 d S T P . .
O2 O -0.0757(8) 0.750000 1.0198(5) 0.0138(14) Uani 1 2 d S T P . .
O3 O 0.0192(7) 0.6681(3) 0.6563(4) 0.0239(12) Uani 1 1 d . . . . .
O4 O 0.2755(7) 0.6719(4) 0.6848(4) 0.0350(15) Uani 1 1 d . . . . .
C2 C 0.1804(9) 0.5961(4) 0.5333(6) 0.0181(15) Uani 1 1 d . . . . .
O5 O 0.4373(7) 0.3855(3) 0.5725(4) 0.0287(13) Uani 1 1 d . . . . .
C11 C -0.1858(13) 0.750000 0.3156(9) 0.023(2) Uani 1 2 d S T P . .
H11 H -0.283260 0.750000 0.277123 0.028 Uiso 1 2 calc R U P . .
O1 O 0.2623(12) 0.750000 0.9119(9) 0.050(3) Uani 1 2 d S T P . .
O6 O 0.4150(10) 0.3680(4) 0.3910(5) 0.056(2) Uani 1 1 d . . . . .
C5 C 0.3860(11) 0.4052(5) 0.4775(7) 0.0291(19) Uani 1 1 d . . . . .
C10 C -0.1139(9) 0.6811(4) 0.3440(6) 0.0211(16) Uani 1 1 d . . . . .
H10 H -0.159189 0.633028 0.323075 0.025 Uiso 1 1 calc R U . . .
C8 C 0.1099(9) 0.6096(4) 0.4299(6) 0.0191(15) Uani 1 1 d . . . . .
C9 C 0.0256(9) 0.6834(4) 0.4037(6) 0.0186(15) Uani 1 1 d . . . . .
C7 C 0.1254(10) 0.5546(4) 0.3464(6) 0.0227(17) Uani 1 1 d . . . . .
H7 H 0.075149 0.562583 0.277088 0.027 Uiso 1 1 calc R U . . .
C1 C 0.1577(10) 0.6499(4) 0.6306(6) 0.0216(16) Uani 1 1 d . . . . .
C3 C 0.2690(9) 0.5286(4) 0.5499(6) 0.0203(16) Uani 1 1 d . . . . .
H3 H 0.317705 0.519285 0.619444 0.024 Uiso 1 1 calc R U . . .
C4 C 0.2854(9) 0.4754(4) 0.4646(6) 0.0203(16) Uani 1 1 d . . . . .
C6 C 0.2128(9) 0.4889(4) 0.3635(6) 0.0217(16) Uani 1 1 d . . . . .
H6 H 0.223621 0.452253 0.305383 0.026 Uiso 1 1 calc 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
GD1 O6 2.322(6) 7_666 ?
GD1 O6 2.322(6) 2_565 ?
GD1 O4 2.367(6) 6_557 ?
GD1 O4 2.367(6) 3_466 ?
GD1 O3 2.425(5) . ?
GD1 O3 2.425(5) 8_575 ?
GD1 O1 2.465(10) . ?
GD1 O2 2.517(6) . ?
N1 C9 1.349(8) 8_575 ?
N1 C9 1.349(8) . ?
O3 C1 1.259(9) . ?
O4 C1 1.255(10) . ?
O4 GD1 2.366(6) 6_657 ?
C2 C8 1.403(10) . ?
C2 C3 1.405(10) . ?
C2 C1 1.510(10) . ?
O5 C5 1.273(9) . ?
C11 C10 1.383(9) 8_575 ?
C11 C10 1.383(9) . ?
C11 H11 0.9500 . ?
O6 C5 1.252(9) . ?
O6 GD1 2.322(6) 2_564 ?
C5 C4 1.492(10) . ?
C10 C9 1.389(10) . ?
C10 H10 0.9500 . ?
C8 C7 1.392(10) . ?
C8 C9 1.498(10) . ?
C7 C6 1.373(10) . ?
C7 H7 0.9500 . ?
C3 C4 1.387(9) . ?
C3 H3 0.9500 . ?
C4 C6 1.388(10) . ?
C6 H6 0.9500 . ?

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 GD1 O6 123.0(4) 7_666 2_565 ?
O6 GD1 O4 138.8(2) 7_666 6_557 ?
O6 GD1 O4 75.5(3) 2_565 6_557 ?
O6 GD1 O4 75.5(3) 7_666 3_466 ?
O6 GD1 O4 138.8(2) 2_565 3_466 ?
O4 GD1 O4 69.6(3) 6_557 3_466 ?
O6 GD1 O3 143.2(2) 7_666 . ?
O6 GD1 O3 76.9(2) 2_565 . ?
O4 GD1 O3 72.21(19) 6_557 . ?
O4 GD1 O3 111.2(2) 3_466 . ?
O6 GD1 O3 76.9(2) 7_666 8_575 ?
O6 GD1 O3 143.2(2) 2_565 8_575 ?
O4 GD1 O3 111.2(2) 6_557 8_575 ?
O4 GD1 O3 72.21(19) 3_466 8_575 ?
O3 GD1 O3 71.5(2) . 8_575 ?
O6 GD1 O1 64.3(2) 7_666 . ?
O6 GD1 O1 64.3(2) 2_565 . ?
O4 GD1 O1 137.7(2) 6_557 . ?
O4 GD1 O1 137.7(2) 3_466 . ?
O3 GD1 O1 108.7(2) . . ?
O3 GD1 O1 108.7(2) 8_575 . ?
O6 GD1 O2 73.72(16) 7_666 . ?
O6 GD1 O2 73.72(16) 2_565 . ?
O4 GD1 O2 78.32(18) 6_557 . ?
O4 GD1 O2 78.32(18) 3_466 . ?
O3 GD1 O2 142.59(13) . . ?
O3 GD1 O2 142.59(13) 8_575 . ?
O1 GD1 O2 78.6(3) . . ?
C9 N1 C9 117.2(9) 8_575 . ?
C1 O3 GD1 113.3(5) . . ?
C1 O4 GD1 144.9(5) . 6_657 ?
C8 C2 C3 119.6(7) . . ?
C8 C2 C1 122.3(7) . . ?
C3 C2 C1 118.0(6) . . ?
C10 C11 C10 119.1(10) 8_575 . ?
C10 C11 H11 120.4 8_575 . ?
C10 C11 H11 120.4 . . ?
C5 O6 GD1 145.4(6) . 2_564 ?
O6 C5 O5 123.1(7) . . ?
O6 C5 C4 116.4(7) . . ?
O5 C5 C4 120.5(7) . . ?
C11 C10 C9 118.8(7) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C7 C8 C2 119.3(7) . . ?
C7 C8 C9 118.3(7) . . ?
C2 C8 C9 122.2(7) . . ?
N1 C9 C10 123.1(7) . . ?
N1 C9 C8 117.2(7) . . ?
C10 C9 C8 119.6(7) . . ?
C6 C7 C8 120.5(7) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
O3 C1 O4 122.8(7) . . ?
O3 C1 C2 117.8(7) . . ?
O4 C1 C2 119.4(7) . . ?
C4 C3 C2 120.0(7) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C6 C4 C3 119.7(7) . . ?
C6 C4 C5 118.9(7) . . ?
C3 C4 C5 121.3(7) . . ?
C7 C6 C4 120.8(7) . . ?
C7 C6 H6 119.6 . . ?
C4 C6 H6 119.6 . . ?

_refine_diff_density_max         1.855
_refine_diff_density_min         -1.565
_refine_diff_density_rms         0.155



####################################################################### 
# 
# 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_TbL
_database_code_depnum_ccdc_archive 'CCDC 1505267'
_audit_update_record             
;
2016-09-20 deposited with the CCDC.
2017-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10.50 H4.50 N0.50 O5 Tb0.50'
_chemical_formula_weight         297.11

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   8.5052(2)
_cell_length_b                   17.3256(4)
_cell_length_c                   12.0864(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1781.02(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    3134
_cell_measurement_theta_min      4.4430
_cell_measurement_theta_max      72.8430

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.216
_exptl_crystal_F_000             1148
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    20.170
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.44354
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova (Cu) X-ray Source'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            6711
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.460
_diffrn_reflns_theta_max         73.356
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1820
_reflns_number_gt                1585
_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.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0458P)²+12.2841P] 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         1820
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1014
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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 0.50290(5) 0.250000 0.68086(3) 0.01296(15) Uani 1 2 d S T P . .
C9 C 0.0268(6) 0.3172(3) 0.4034(4) 0.0171(10) Uani 1 1 d . . . . .
O2 O 0.4247(6) 0.250000 0.4796(4) 0.0167(9) Uani 1 2 d S T P . .
O5 O 0.4363(5) 0.6144(2) 0.5729(3) 0.0235(8) Uani 1 1 d . . . . .
O4 O 0.2749(5) 0.3282(2) 0.6846(3) 0.0300(9) Uani 1 1 d . . . . .
C8 C 0.1109(5) 0.3898(3) 0.4309(4) 0.0157(9) Uani 1 1 d . . . . .
N1 N 0.0957(7) 0.250000 0.4344(4) 0.0141(11) Uani 1 2 d S T P . .
O6 O 0.4169(6) 0.6311(2) 0.3912(3) 0.0432(12) Uani 1 1 d . . . . .
C7 C 0.1272(6) 0.4446(3) 0.3472(4) 0.0210(10) Uani 1 1 d . . . . .
H7 H 0.078401 0.436199 0.277512 0.025 Uiso 1 1 calc R U . . .
O3 O 0.0192(5) 0.3321(2) 0.6562(3) 0.0266(9) Uani 1 1 d . . . . .
C4 C 0.2870(6) 0.5240(3) 0.4653(4) 0.0202(10) Uani 1 1 d . . . . .
C3 C 0.2692(6) 0.4703(3) 0.5499(4) 0.0191(10) Uani 1 1 d . . . . .
H3 H 0.318196 0.479157 0.619431 0.023 Uiso 1 1 calc R U . . .
C11 C -0.1852(10) 0.250000 0.3158(6) 0.0257(16) Uani 1 2 d S T P . .
H11 H -0.282299 0.250000 0.277008 0.031 Uiso 1 2 calc R U P . .
C10 C -0.1130(6) 0.3189(3) 0.3447(4) 0.0211(10) Uani 1 1 d . . . . .
H10 H -0.159021 0.366819 0.324296 0.025 Uiso 1 1 calc R U . . .
O1 O 0.7613(8) 0.250000 0.5890(6) 0.0445(16) Uani 1 2 d S T P . .
C2 C 0.1806(6) 0.4037(3) 0.5340(4) 0.0162(9) Uani 1 1 d . . . . .
C6 C 0.2137(6) 0.5110(3) 0.3646(4) 0.0236(11) Uani 1 1 d . . . . .
H6 H 0.222938 0.548049 0.307048 0.028 Uiso 1 1 calc R U . . .
C5 C 0.3864(7) 0.5951(3) 0.4777(5) 0.0258(11) Uani 1 1 d . . . . .
C1 C 0.1567(6) 0.3503(3) 0.6304(4) 0.0202(10) 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 2.339(4) 4_646 ?
TB1 O6 2.339(4) 5_666 ?
TB1 O4 2.366(4) . ?
TB1 O4 2.366(4) 8_565 ?
TB1 O3 2.434(4) 6_657 ?
TB1 O3 2.434(4) 3_556 ?
TB1 O1 2.462(7) . ?
TB1 O2 2.522(5) . ?
C9 N1 1.356(6) . ?
C9 C10 1.386(7) . ?
C9 C8 1.484(6) . ?
O5 C5 1.272(7) . ?
O4 C1 1.260(6) . ?
C8 C7 1.395(7) . ?
C8 C2 1.401(7) . ?
N1 C9 1.356(6) 8_565 ?
O6 C5 1.245(7) . ?
O6 TB1 2.339(4) 5_666 ?
C7 C6 1.381(7) . ?
O3 C1 1.251(6) . ?
O3 TB1 2.434(4) 6_557 ?
C4 C6 1.386(8) . ?
C4 C3 1.392(7) . ?
C4 C5 1.500(7) . ?
C3 C2 1.391(7) . ?
C11 C10 1.387(7) . ?
C11 C10 1.387(6) 8_565 ?
C2 C1 1.502(6) . ?

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 O6 123.5(3) 4_646 5_666 ?
O6 TB1 O4 138.66(16) 4_646 . ?
O6 TB1 O4 75.04(17) 5_666 . ?
O6 TB1 O4 75.04(17) 4_646 8_565 ?
O6 TB1 O4 138.66(16) 5_666 8_565 ?
O4 TB1 O4 69.9(2) . 8_565 ?
O6 TB1 O3 143.11(14) 4_646 6_657 ?
O6 TB1 O3 76.68(14) 5_666 6_657 ?
O4 TB1 O3 72.33(13) . 6_657 ?
O4 TB1 O3 111.46(13) 8_565 6_657 ?
O6 TB1 O3 76.68(14) 4_646 3_556 ?
O6 TB1 O3 143.11(14) 5_666 3_556 ?
O4 TB1 O3 111.46(13) . 3_556 ?
O4 TB1 O3 72.33(13) 8_565 3_556 ?
O3 TB1 O3 71.55(19) 6_657 3_556 ?
O6 TB1 O1 64.64(14) 4_646 . ?
O6 TB1 O1 64.64(14) 5_666 . ?
O4 TB1 O1 137.75(13) . . ?
O4 TB1 O1 137.75(13) 8_565 . ?
O3 TB1 O1 108.31(16) 6_657 . ?
O3 TB1 O1 108.31(16) 3_556 . ?
O6 TB1 O2 73.61(11) 4_646 . ?
O6 TB1 O2 73.61(11) 5_666 . ?
O4 TB1 O2 78.59(12) . . ?
O4 TB1 O2 78.59(12) 8_565 . ?
O3 TB1 O2 142.72(10) 6_657 . ?
O3 TB1 O2 142.72(10) 3_556 . ?
O1 TB1 O2 78.5(2) . . ?
N1 C9 C10 122.0(5) . . ?
N1 C9 C8 117.2(4) . . ?
C10 C9 C8 120.7(4) . . ?
C1 O4 TB1 144.9(3) . . ?
C7 C8 C2 119.1(4) . . ?
C7 C8 C9 117.5(4) . . ?
C2 C8 C9 123.3(4) . . ?
C9 N1 C9 118.3(6) . 8_565 ?
C5 O6 TB1 144.6(4) . 5_666 ?
C6 C7 C8 120.6(5) . . ?
C1 O3 TB1 113.7(3) . 6_557 ?
C6 C4 C3 119.2(5) . . ?
C6 C4 C5 118.4(5) . . ?
C3 C4 C5 122.4(5) . . ?
C2 C3 C4 120.8(5) . . ?
C10 C11 C10 118.8(7) . 8_565 ?
C11 C10 C9 119.4(5) . . ?
C3 C2 C8 119.7(4) . . ?
C3 C2 C1 118.5(4) . . ?
C8 C2 C1 121.8(4) . . ?
C7 C6 C4 120.6(5) . . ?
O6 C5 O5 124.0(5) . . ?
O6 C5 C4 116.4(5) . . ?
O5 C5 C4 119.6(5) . . ?
O3 C1 O4 122.7(5) . . ?
O3 C1 C2 118.3(5) . . ?
O4 C1 C2 118.9(5) . . ?

_refine_diff_density_max         1.741
_refine_diff_density_min         -1.299
_refine_diff_density_rms         0.139



