# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1886731'
_audit_update_record             
;
2018-12-21 deposited with the CCDC.
2019-02-04 downloaded from the CCDC.
;
_audit_creation_date             2018-01-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.25(C56 H28 N8 Nd4 O32)'
_chemical_formula_sum            'C14 H7 N2 Nd O8'
_chemical_formula_weight         475.46
_chemical_melting_point          ?
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'
Nd Nd -0.1943 3.0179 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.973(4)
_cell_length_b                   8.757(4)
_cell_length_c                   15.809(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1380.6(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4574
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4807
_cell_measurement_theta_min      1.2880
_shelx_estimated_absorpt_T_max   0.625
_shelx_estimated_absorpt_T_min   0.321
_exptl_absorpt_coefficient_mu    3.814
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             916
_exptl_crystal_size_max          0.386
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.136
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5346
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         3.289
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1503
_reflns_number_total             1549
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.803
_refine_diff_density_min         -0.948
_refine_diff_density_rms         0.191
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1549
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.156
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0579P)²+1.4610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0925
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: H3(0.5)
3.a Riding coordinates:
 O3(H3)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Nd1 Nd 0.500000 0.59006(2) 0.250000 0.00861(16) Uani 1 2 d S T P . .
N1 N 0.0717(2) 0.2386(2) 0.38669(13) 0.0115(4) Uani 1 1 d . . . . .
O1 O 0.2799(2) 0.4925(2) 0.27240(14) 0.0187(4) Uani 1 1 d . . . . .
C1 C 0.1526(3) 0.3587(3) 0.37443(16) 0.0133(5) Uani 1 1 d . . . . .
C2 C 0.1965(3) 0.4505(3) 0.44071(17) 0.0190(6) Uani 1 1 d . . . . .
H2 H 0.250256 0.535104 0.430024 0.023 Uiso 1 1 calc R . . . .
O2 O 0.1495(2) 0.3026(2) 0.22748(14) 0.0146(4) Uani 1 1 d . . . . .
O3 O 0.0279(3) 0.3435(3) 0.67611(16) 0.0263(5) Uani 1 1 d . . . . .
H3 H 0.017935 0.351439 0.728054 0.039 Uiso 0.5 1 d R . . . .
C3 C 0.1592(3) 0.4146(3) 0.52306(18) 0.0190(6) Uani 1 1 d . . . . .
H3A H 0.187694 0.475902 0.569259 0.023 Uiso 1 1 calc R . . . .
C4 C 0.0793(3) 0.2868(3) 0.53613(16) 0.0137(5) Uani 1 1 d . . . . .
O4 O 0.0238(3) 0.0980(3) 0.6369(2) 0.0216(6) Uani 1 1 d . . . . .
C5 C 0.0356(3) 0.2042(3) 0.46598(18) 0.0127(5) Uani 1 1 d . . . . .
H5 H -0.022525 0.119719 0.474841 0.015 Uiso 1 1 calc R . . . .
C6 C 0.1973(3) 0.3877(3) 0.28368(16) 0.0127(5) Uani 1 1 d . . . . .
C7 C 0.0404(3) 0.2360(3) 0.62276(18) 0.0164(5) 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
Nd1 N1 2.622(2) 8_665 ?
Nd1 N1 2.622(2) 6_666 ?
Nd1 O1 2.382(2) 3_655 ?
Nd1 O1 2.382(2) . ?
Nd1 O2 2.411(2) 6_666 ?
Nd1 O2 2.411(2) 8_665 ?
Nd1 O4 2.442(3) 2_554 ?
Nd1 O4 2.442(3) 4_556 ?
N1 C1 1.339(3) . ?
N1 C5 1.339(4) . ?
O1 C6 1.246(3) . ?
C1 C2 1.391(4) . ?
C1 C6 1.523(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(4) . ?
O2 C6 1.254(4) . ?
O3 H3 0.8300 . ?
O3 C7 1.270(4) . ?
C3 H3A 0.9500 . ?
C3 C4 1.389(4) . ?
C4 C5 1.394(4) . ?
C4 C7 1.492(4) . ?
O4 C7 1.240(4) . ?
C5 H5 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
N1 Nd1 N1 120.50(9) 8_665 6_666 ?
O1 Nd1 N1 123.50(7) . 6_666 ?
O1 Nd1 N1 78.70(7) . 8_665 ?
O1 Nd1 N1 78.70(7) 3_655 6_666 ?
O1 Nd1 N1 123.50(7) 3_655 8_665 ?
O1 Nd1 O1 137.96(11) 3_655 . ?
O1 Nd1 O2 145.57(7) 3_655 8_665 ?
O1 Nd1 O2 74.27(8) 3_655 6_666 ?
O1 Nd1 O2 145.57(7) . 6_666 ?
O1 Nd1 O2 74.27(8) . 8_665 ?
O1 Nd1 O4 74.87(9) . 4_556 ?
O1 Nd1 O4 74.87(9) 3_655 2_554 ?
O1 Nd1 O4 77.14(9) . 2_554 ?
O1 Nd1 O4 77.14(9) 3_655 4_556 ?
O2 Nd1 N1 70.37(7) 8_665 6_666 ?
O2 Nd1 N1 64.53(7) 6_666 6_666 ?
O2 Nd1 N1 70.37(7) 6_666 8_665 ?
O2 Nd1 N1 64.53(7) 8_665 8_665 ?
O2 Nd1 O2 78.97(10) 6_666 8_665 ?
O2 Nd1 O4 110.61(9) 8_665 2_554 ?
O2 Nd1 O4 133.52(9) 8_665 4_556 ?
O2 Nd1 O4 133.52(9) 6_666 2_554 ?
O2 Nd1 O4 110.61(9) 6_666 4_556 ?
O4 Nd1 N1 75.97(9) 2_554 6_666 ?
O4 Nd1 N1 155.71(9) 2_554 8_665 ?
O4 Nd1 N1 155.71(9) 4_556 6_666 ?
O4 Nd1 N1 75.97(9) 4_556 8_665 ?
O4 Nd1 O4 95.22(15) 2_554 4_556 ?
C1 N1 Nd1 115.76(16) . 6_556 ?
C5 N1 Nd1 125.91(17) . 6_556 ?
C5 N1 C1 118.3(2) . . ?
C6 O1 Nd1 153.5(2) . . ?
N1 C1 C2 122.3(2) . . ?
N1 C1 C6 116.3(2) . . ?
C2 C1 C6 121.4(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.4(2) . . ?
C3 C2 H2 120.3 . . ?
C6 O2 Nd1 126.10(18) . 6_556 ?
C7 O3 H3 137.0 . . ?
C2 C3 H3A 120.8 . . ?
C4 C3 C2 118.4(2) . . ?
C4 C3 H3A 120.8 . . ?
C3 C4 C5 118.6(2) . . ?
C3 C4 C7 121.8(2) . . ?
C5 C4 C7 119.6(2) . . ?
C7 O4 Nd1 143.3(3) . 2 ?
N1 C5 C4 122.9(2) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
O1 C6 C1 116.8(2) . . ?
O1 C6 O2 126.0(3) . . ?
O2 C6 C1 117.2(2) . . ?
O3 C7 C4 114.5(2) . . ?
O4 C7 O3 126.1(3) . . ?
O4 C7 C4 119.4(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O3 0.83 1.58 2.401(5) 167.7 3_556

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
Nd1 N1 C1 C2 178.5(2) 6_556 . . . ?
Nd1 N1 C1 C6 -2.9(3) 6_556 . . . ?
Nd1 N1 C5 C4 178.87(19) 6_556 . . . ?
Nd1 O1 C6 C1 99.5(4) . . . . ?
Nd1 O1 C6 O2 -79.1(5) . . . . ?
Nd1 O2 C6 O1 176.0(2) 6_556 . . . ?
Nd1 O2 C6 C1 -2.6(3) 6_556 . . . ?
Nd1 O4 C7 O3 -13.6(7) 2 . . . ?
Nd1 O4 C7 C4 166.0(3) 2 . . . ?
N1 C1 C2 C3 2.1(4) . . . . ?
N1 C1 C6 O1 -175.1(2) . . . . ?
N1 C1 C6 O2 3.6(4) . . . . ?
C1 N1 C5 C4 -0.6(4) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C1 C6 O1 3.5(4) . . . . ?
C2 C1 C6 O2 -177.8(3) . . . . ?
C2 C3 C4 C5 -2.6(4) . . . . ?
C2 C3 C4 C7 177.0(3) . . . . ?
C3 C4 C5 N1 2.9(4) . . . . ?
C3 C4 C7 O3 31.5(4) . . . . ?
C3 C4 C7 O4 -148.2(3) . . . . ?
C5 N1 C1 C2 -1.9(4) . . . . ?
C5 N1 C1 C6 176.6(2) . . . . ?
C5 C4 C7 O3 -148.9(3) . . . . ?
C5 C4 C7 O4 31.4(4) . . . . ?
C6 C1 C2 C3 -176.4(3) . . . . ?
C7 C4 C5 N1 -176.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
