# 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_sa5244
_audit_block_doi                 10.5517/ccdc.csd.cc21b9c2
_database_code_depnum_ccdc_archive 'CCDC 1886733'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8TC06445H 2019
loop_
_audit_author_name
_audit_author_address
'Chuanlang Zhan'
;Institute of Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2018-12-21 deposited with the CCDC.	2019-02-13 downloaded from the CCDC.
;
_audit_creation_date             2017-11-07
_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         '0.5(C42 H26 N6 Nd4 O28)'
_chemical_formula_sum            'C21 H13 N3 Nd2 O14'
_chemical_formula_weight         819.82
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   6.4925(13)
_cell_length_b                   17.852(4)
_cell_length_c                   9.350(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.942(3)
_cell_angle_gamma                90
_cell_volume                     1079.7(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3568
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4839
_cell_measurement_theta_min      2.1683
_shelx_estimated_absorpt_T_max   0.620
_shelx_estimated_absorpt_T_min   0.333
_exptl_absorpt_coefficient_mu    4.846
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46277
_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    2.522
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.291
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.109
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8672
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         3.149
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2426
_reflns_number_total             2474
_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         1.368
_refine_diff_density_min         -1.491
_refine_diff_density_rms         0.164
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2474
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.167
_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)+(0.0229P)²+4.2487P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0757
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H,H) groups, H1 of C1X
 At 1.2 times of:
  H5 of C5, H2 of C2, H3 of C3, H10 of C10
2. Shared sites
{N1, C1X}
3. Uiso/Uaniso restraints and constraints
Uiso(N1) = Uiso(C1X)
4. Others
 Fixed Sof: N1(0.5) C1X(0.5) H1(0.5)
5.a Riding coordinates:
 C10(H10), C1X(H1), O7(H7A,H7B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), 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
C1 C 0.3496(6) 0.4487(2) 0.2380(5) 0.0129(8) Uani 1 1 d . . . . .
C2 C 0.2670(7) 0.4511(2) 0.0962(5) 0.0162(9) Uani 1 1 d . . . . .
H2 H 0.221919 0.406471 0.047764 0.019 Uiso 1 1 calc R . . . .
C3 C 0.2512(7) 0.5197(3) 0.0264(5) 0.0183(9) Uani 1 1 d . . . . .
H3 H 0.195380 0.522737 -0.070776 0.022 Uiso 1 1 calc R . . . .
C4 C 0.3178(6) 0.5836(2) 0.1000(5) 0.0140(8) Uani 1 1 d . . . . .
C5 C 0.4069(6) 0.5167(2) 0.3050(5) 0.0144(8) Uani 1 1 d . . . . .
H5 H 0.459980 0.515550 0.402943 0.017 Uiso 1 1 calc R . . . .
C6 C 0.3823(6) 0.3759(2) 0.3172(5) 0.0128(8) Uani 1 1 d . . . . .
C7 C 0.3264(6) 0.6581(2) 0.0258(5) 0.0140(8) Uani 1 1 d . . . . .
C8 C 1.0278(7) 0.3570(3) 0.6384(5) 0.0173(9) Uani 1 1 d . . . . .
C9 C 1.0138(6) 0.4321(2) 0.5650(5) 0.0160(9) Uani 1 1 d . . . . .
C10 C 1.0898(7) 0.5602(3) 0.5700(5) 0.0191(9) Uani 1 1 d . . . . .
H10 H 1.147975 0.602200 0.616639 0.023 Uiso 1 1 d R . . . .
N1 N 1.1059(6) 0.4922(2) 0.6368(4) 0.0184(8) Uiso 0.5 1 d . . P . .
C1X C 1.1059(6) 0.4922(2) 0.6368(4) 0.0184(8) Uiso 0.5 1 d . . P . .
H1 H 1.210665 0.485315 0.730433 0.028 Uiso 0.5 1 d R . P . .
N2 N 0.3911(5) 0.5829(2) 0.2387(4) 0.0132(7) Uani 1 1 d . . . . .
Nd1 Nd 0.51213(3) 0.28518(2) 0.63359(2) 0.01099(9) Uani 1 1 d . . . . .
O1 O 0.4460(5) 0.37844(17) 0.4479(3) 0.0157(6) Uani 1 1 d . . . . .
O2 O 0.3418(5) 0.31707(17) 0.2467(3) 0.0171(6) Uani 1 1 d . . . . .
O3 O 0.2890(5) 0.66182(17) -0.1060(3) 0.0185(7) Uani 1 1 d . . . . .
O4 O 0.3842(5) 0.71505(15) 0.1031(3) 0.0149(6) Uani 1 1 d . . . . .
O5 O 0.8755(5) 0.31359(18) 0.6207(4) 0.0238(7) Uani 1 1 d . . . . .
O6 O 1.1941(5) 0.34101(17) 0.7119(3) 0.0174(6) Uani 1 1 d . . . . .
O7 O 0.1969(5) 0.23458(19) 0.4813(3) 0.0197(7) Uani 1 1 d . . . . .
H7A H 0.085860 0.243341 0.524502 0.030 Uiso 1 1 d R . . . .
H7B H 0.169480 0.227861 0.389472 0.030 Uiso 1 1 d R . . . .


_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
C1 C2 1.387(6) . ?
C1 C5 1.401(6) . ?
C1 C6 1.502(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(6) . ?
C4 C7 1.504(6) . ?
C4 N2 1.342(5) . ?
C5 H5 0.9500 . ?
C5 N2 1.335(6) . ?
C6 O1 1.257(5) . ?
C6 O2 1.256(5) . ?
C7 Nd1 2.955(4) 2_655 ?
C7 O3 1.238(5) . ?
C7 O4 1.284(5) . ?
C8 C9 1.505(6) . ?
C8 O5 1.256(5) . ?
C8 O6 1.262(5) . ?
C9 C10 1.385(6) 3_766 ?
C9 N1 1.375(6) . ?
C10 H10 0.9301 . ?
C10 N1 1.365(6) . ?
N1 H1 1.0686 . ?
N2 Nd1 2.691(4) 3_666 ?
Nd1 O1 2.417(3) . ?
Nd1 O2 2.424(3) 4_566 ?
Nd1 O3 2.577(3) 2_645 ?
Nd1 O4 2.679(3) 2_645 ?
Nd1 O4 2.496(3) 3_666 ?
Nd1 O5 2.426(3) . ?
Nd1 O6 2.460(3) 1_455 ?
Nd1 O7 2.556(3) . ?
O7 H7A 0.8701 . ?
O7 H7B 0.8700 . ?

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
C2 C1 C5 117.9(4) . . ?
C2 C1 C6 121.6(4) . . ?
C5 C1 C6 120.5(4) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 118.9(4) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.1(4) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C7 121.5(4) . . ?
N2 C4 C3 122.9(4) . . ?
N2 C4 C7 115.5(4) . . ?
C1 C5 H5 118.3 . . ?
N2 C5 C1 123.5(4) . . ?
N2 C5 H5 118.3 . . ?
O1 C6 C1 118.0(4) . . ?
O2 C6 C1 116.7(4) . . ?
O2 C6 O1 125.3(4) . . ?
C4 C7 Nd1 160.2(3) . 2_655 ?
O3 C7 C4 119.7(4) . . ?
O3 C7 Nd1 60.3(2) . 2_655 ?
O3 C7 O4 122.8(4) . . ?
O4 C7 C4 117.5(4) . . ?
O4 C7 Nd1 65.0(2) . 2_655 ?
O5 C8 C9 118.3(4) . . ?
O5 C8 O6 124.0(4) . . ?
O6 C8 C9 117.7(4) . . ?
C10 C9 C8 120.6(4) 3_766 . ?
N1 C9 C8 117.8(4) . . ?
N1 C9 C10 121.6(4) . 3_766 ?
C9 C10 H10 119.5 3_766 . ?
N1 C10 C9 121.1(4) . 3_766 ?
N1 C10 H10 119.4 . . ?
C9 N1 H1 121.9 . . ?
C10 N1 C9 117.3(4) . . ?
C10 N1 H1 119.7 . . ?
C4 N2 Nd1 118.1(3) . 3_666 ?
C5 N2 C4 117.7(4) . . ?
C5 N2 Nd1 124.3(3) . 3_666 ?
N2 Nd1 C7 144.71(11) 3_666 2_645 ?
O1 Nd1 C7 102.43(11) . 2_645 ?
O1 Nd1 N2 74.69(10) . 3_666 ?
O1 Nd1 O2 140.59(11) . 4_566 ?
O1 Nd1 O3 125.20(10) . 2_645 ?
O1 Nd1 O4 136.53(10) . 3_666 ?
O1 Nd1 O4 76.72(10) . 2_645 ?
O1 Nd1 O5 86.20(11) . . ?
O1 Nd1 O6 80.38(11) . 1_455 ?
O1 Nd1 O7 76.06(10) . . ?
O2 Nd1 C7 80.62(12) 4_566 2_645 ?
O2 Nd1 N2 124.30(11) 4_566 3_666 ?
O2 Nd1 O3 69.60(11) 4_566 2_645 ?
O2 Nd1 O4 70.29(10) 4_566 3_666 ?
O2 Nd1 O4 99.50(10) 4_566 2_645 ?
O2 Nd1 O5 131.40(11) 4_566 . ?
O2 Nd1 O6 75.47(11) 4_566 1_455 ?
O2 Nd1 O7 66.63(11) 4_566 . ?
O3 Nd1 C7 24.66(11) 2_645 2_645 ?
O3 Nd1 N2 133.83(10) 2_645 3_666 ?
O3 Nd1 O4 49.78(9) 2_645 2_645 ?
O4 Nd1 C7 25.75(10) 2_645 2_645 ?
O4 Nd1 C7 114.78(11) 3_666 2_645 ?
O4 Nd1 N2 135.24(10) 2_645 3_666 ?
O4 Nd1 N2 62.02(10) 3_666 3_666 ?
O4 Nd1 O3 90.14(10) 3_666 2_645 ?
O4 Nd1 O4 138.48(10) 3_666 2_645 ?
O4 Nd1 O7 133.16(10) 3_666 . ?
O5 Nd1 C7 75.34(11) . 2_645 ?
O5 Nd1 N2 69.39(11) . 3_666 ?
O5 Nd1 O3 71.09(11) . 2_645 ?
O5 Nd1 O4 75.06(11) . 2_645 ?
O5 Nd1 O4 82.45(12) . 3_666 ?
O5 Nd1 O6 140.77(11) . 1_455 ?
O5 Nd1 O7 141.43(11) . . ?
O6 Nd1 C7 143.53(11) 1_455 2_645 ?
O6 Nd1 N2 71.53(11) 1_455 3_666 ?
O6 Nd1 O3 144.74(11) 1_455 2_645 ?
O6 Nd1 O4 135.42(10) 1_455 2_645 ?
O6 Nd1 O4 82.47(11) 1_455 3_666 ?
O6 Nd1 O7 69.91(11) 1_455 . ?
O7 Nd1 C7 75.50(11) . 2_645 ?
O7 Nd1 N2 134.58(11) . 3_666 ?
O7 Nd1 O3 91.52(11) . 2_645 ?
O7 Nd1 O4 67.71(10) . 2_645 ?
C6 O1 Nd1 134.2(3) . . ?
C6 O2 Nd1 140.9(3) . 4_565 ?
C7 O3 Nd1 95.1(3) . 2_655 ?
C7 O4 Nd1 89.2(3) . 2_655 ?
C7 O4 Nd1 126.5(3) . 3_666 ?
Nd1 O4 Nd1 138.61(12) 3_666 2_655 ?
C8 O5 Nd1 151.7(3) . . ?
C8 O6 Nd1 129.1(3) . 1_655 ?
Nd1 O7 H7A 109.5 . . ?
Nd1 O7 H7B 133.2 . . ?
H7A O7 H7B 112.1 . . ?

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
O7 H7A O5 0.87 2.11 2.917(5) 153.7 1_455
O7 H7B O2 0.87 2.41 2.868(5) 112.9 .
O7 H7B O6 0.87 2.08 2.856(5) 147.7 4_465

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
C1 C2 C3 C4 -0.1(7) . . . . ?
C1 C5 N2 C4 -0.6(6) . . . . ?
C1 C5 N2 Nd1 177.9(3) . . . 3_666 ?
C1 C6 O1 Nd1 176.5(3) . . . . ?
C1 C6 O2 Nd1 104.2(5) . . . 4_565 ?
C2 C1 C5 N2 -1.8(6) . . . . ?
C2 C1 C6 O1 -175.7(4) . . . . ?
C2 C1 C6 O2 3.8(6) . . . . ?
C2 C3 C4 C7 173.2(4) . . . . ?
C2 C3 C4 N2 -2.4(7) . . . . ?
C3 C4 C7 Nd1 -90.0(9) . . . 2_655 ?
C3 C4 C7 O3 -5.8(6) . . . . ?
C3 C4 C7 O4 177.9(4) . . . . ?
C3 C4 N2 C5 2.8(6) . . . . ?
C3 C4 N2 Nd1 -175.9(3) . . . 3_666 ?
C4 C7 O3 Nd1 -157.1(3) . . . 2_655 ?
C4 C7 O4 Nd1 158.0(3) . . . 2_655 ?
C4 C7 O4 Nd1 0.6(5) . . . 3_666 ?
C5 C1 C2 C3 2.1(6) . . . . ?
C5 C1 C6 O1 5.8(6) . . . . ?
C5 C1 C6 O2 -174.7(4) . . . . ?
C6 C1 C2 C3 -176.4(4) . . . . ?
C6 C1 C5 N2 176.7(4) . . . . ?
C7 C4 N2 C5 -173.1(4) . . . . ?
C7 C4 N2 Nd1 8.3(5) . . . 3_666 ?
C8 C9 N1 C10 -179.2(4) . . . . ?
C9 C8 O5 Nd1 -56.7(8) . . . . ?
C9 C8 O6 Nd1 -86.0(5) . . . 1_655 ?
C9 C10 N1 C9 -0.5(7) 3_766 . . . ?
C10 C9 N1 C10 0.5(7) 3_766 . . . ?
N2 C4 C7 Nd1 86.0(9) . . . 2_655 ?
N2 C4 C7 O3 170.1(4) . . . . ?
N2 C4 C7 O4 -6.2(6) . . . . ?
Nd1 C7 O4 Nd1 -157.5(3) 2_655 . . 3_666 ?
O1 C6 O2 Nd1 -76.4(6) . . . 4_565 ?
O2 C6 O1 Nd1 -2.9(7) . . . . ?
O3 C7 O4 Nd1 -18.1(4) . . . 2_655 ?
O3 C7 O4 Nd1 -175.6(3) . . . 3_666 ?
O4 C7 O3 Nd1 18.9(4) . . . 2_655 ?
O5 C8 C9 C10 -35.8(6) . . . 3_766 ?
O5 C8 C9 N1 143.9(4) . . . . ?
O5 C8 O6 Nd1 92.7(5) . . . 1_655 ?
O6 C8 C9 C10 142.9(4) . . . 3_766 ?
O6 C8 C9 N1 -37.4(6) . . . . ?
O6 C8 O5 Nd1 124.6(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
