# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_11970
_database_code_depnum_ccdc_archive 'CCDC 2308657'
loop_
_audit_author_name
_audit_author_address
'Liu Hou-Ting'
;Liaocheng University
China
;
_audit_update_record             
;
2023-11-17 deposited with the CCDC.	2024-02-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14.50 H11 N O7.50 Pr'
_chemical_formula_weight         460.15

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'
Pr Pr -2.4164 10.2820 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

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

_cell_length_a                   19.3598(8)
_cell_length_b                   16.8591(7)
_cell_length_c                   8.6034(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2808.0(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1434
_cell_measurement_theta_min      5.2330
_cell_measurement_theta_max      70.9520

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            RED
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.177
_exptl_crystal_F_000             1792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    27.055
_shelx_estimated_absorpt_T_min   0.140
_shelx_estimated_absorpt_T_max   0.155
_exptl_absorpt_correction_T_min  0.41271
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5904
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.476
_diffrn_reflns_theta_max         67.196
_diffrn_reflns_theta_full        67.196
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2506
_reflns_number_gt                1431
_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       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0464P)²] 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         2506
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1223
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_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
Pr1 Pr 0.36968(2) 0.71466(3) 0.00055(7) 0.01638(17) Uani 1 1 d . . . . .
N1 N 0.6861(5) 0.9502(6) 0.5798(11) 0.036(2) Uani 1 1 d . . . . .
C15 C 0.250000 0.750000 0.2125(19) 0.031(4) Uani 1 2 d S T P . .
O1 O 0.4623(4) 0.7706(4) -0.1499(9) 0.0358(19) Uani 1 1 d . . . . .
O2 O 0.4551(4) 0.8573(5) -0.3435(9) 0.040(2) Uani 1 1 d . . . . .
O3 O 0.5943(4) 1.1092(4) -0.3169(8) 0.0308(17) Uani 1 1 d . . . . .
O4 O 0.6282(4) 1.1459(4) -0.0798(8) 0.0327(17) Uani 1 1 d . . . . .
O5 O 0.250000 0.750000 0.0628(12) 0.034(3) Uani 1 2 d S T P . .
O6 O 0.1929(4) 0.7689(4) 0.2774(7) 0.0261(17) Uani 1 1 d . . . . .
O7 O 0.2879(4) 0.5993(5) 0.0167(11) 0.063(3) Uani 1 1 d . . . . .
H7A H 0.302532 0.562038 -0.041132 0.095 Uiso 1 1 d R U . . .
H7C H 0.248202 0.613988 -0.014252 0.095 Uiso 1 1 d R U . . .
O8 O 0.6180(5) 0.8952(4) 0.2389(8) 0.044(2) Uani 1 1 d . . . . .
C1 C 0.4776(5) 0.8356(6) -0.2137(12) 0.025(2) Uani 1 1 d . . . . .
C2 C 0.5274(5) 0.8899(5) -0.1314(10) 0.019(2) Uani 1 1 d . . . . .
C3 C 0.5465(5) 0.9631(6) -0.1960(10) 0.019(2) Uani 1 1 d . . . . .
H3 H 0.531504 0.976919 -0.295094 0.023 Uiso 1 1 calc R U . . .
C4 C 0.5879(5) 1.0149(5) -0.1111(10) 0.018(2) Uani 1 1 d . . . . .
C5 C 0.6108(5) 0.9948(6) 0.0350(9) 0.023(2) Uani 1 1 d . . . . .
H5 H 0.637752 1.030042 0.091715 0.027 Uiso 1 1 calc R U . . .
C6 C 0.5933(5) 0.9212(6) 0.0975(10) 0.022(2) Uani 1 1 d . . . . .
C7 C 0.5506(5) 0.8696(5) 0.0155(11) 0.022(2) Uani 1 1 d . . . . .
H7 H 0.537595 0.821465 0.059502 0.027 Uiso 1 1 calc R U . . .
C8 C 0.6043(5) 1.0963(5) -0.1741(12) 0.023(2) Uani 1 1 d . . . . .
C9 C 0.6057(9) 0.9381(9) 0.3677(14) 0.077(5) Uani 1 1 d . . . . .
H9A H 0.556336 0.939547 0.387358 0.093 Uiso 1 1 calc R U . . .
H9B H 0.621355 0.992111 0.351694 0.093 Uiso 1 1 calc R U . . .
C10 C 0.6419(6) 0.9034(7) 0.5059(13) 0.038(3) Uani 1 1 d . . . . .
C11 C 0.6290(7) 0.8252(8) 0.5462(13) 0.046(3) Uani 1 1 d . . . . .
H11 H 0.599711 0.793567 0.487034 0.055 Uiso 1 1 calc R U . . .
C12 C 0.6612(7) 0.7960(7) 0.6769(14) 0.042(3) Uani 1 1 d . . . . .
H12 H 0.653331 0.744234 0.709523 0.051 Uiso 1 1 calc R U . . .
C13 C 0.7052(7) 0.8448(7) 0.7584(15) 0.045(3) Uani 1 1 d . . . . .
H13 H 0.727624 0.826097 0.846659 0.054 Uiso 1 1 calc R U . . .
C14 C 0.7157(6) 0.9212(7) 0.7086(14) 0.041(3) Uani 1 1 d . . . . .
H14 H 0.744373 0.954120 0.766485 0.049 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
Pr1 O1 2.404(7) . ?
Pr1 O6 2.447(7) 8_655 ?
Pr1 O4 2.449(7) 5_675 ?
Pr1 O2 2.451(7) 7_576 ?
Pr1 O5 2.452(2) . ?
Pr1 O3 2.479(6) 3_644 ?
Pr1 O7 2.512(7) . ?
Pr1 O6 2.687(6) 2_565 ?
N1 C10 1.327(15) . ?
N1 C14 1.339(14) . ?
C15 O6 1.279(10) . ?
C15 O6 1.279(10) 2_565 ?
C15 O5 1.288(18) . ?
O1 C1 1.261(12) . ?
O2 C1 1.253(12) . ?
O3 C8 1.263(11) . ?
O4 C8 1.254(11) . ?
O8 C9 1.344(13) . ?
O8 C6 1.379(10) . ?
C1 C2 1.506(13) . ?
C2 C7 1.384(12) . ?
C2 C3 1.402(12) . ?
C3 C4 1.393(12) . ?
C4 C5 1.375(12) . ?
C4 C8 1.508(12) . ?
C5 C6 1.394(13) . ?
C6 C7 1.392(13) . ?
C9 C10 1.499(15) . ?
C10 C11 1.386(17) . ?
C11 C12 1.376(16) . ?
C12 C13 1.375(17) . ?
C13 C14 1.373(17) . ?

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 Pr1 O6 78.5(2) . 8_655 ?
O1 Pr1 O4 76.1(2) . 5_675 ?
O6 Pr1 O4 82.4(2) 8_655 5_675 ?
O1 Pr1 O2 89.2(3) . 7_576 ?
O6 Pr1 O2 161.5(2) 8_655 7_576 ?
O4 Pr1 O2 108.1(3) 5_675 7_576 ?
O1 Pr1 O5 136.6(2) . . ?
O6 Pr1 O5 67.2(3) 8_655 . ?
O4 Pr1 O5 73.84(18) 5_675 . ?
O2 Pr1 O5 129.7(3) 7_576 . ?
O1 Pr1 O3 74.3(2) . 3_644 ?
O6 Pr1 O3 84.7(2) 8_655 3_644 ?
O4 Pr1 O3 149.5(2) 5_675 3_644 ?
O2 Pr1 O3 78.7(3) 7_576 3_644 ?
O5 Pr1 O3 125.4(2) . 3_644 ?
O1 Pr1 O7 143.5(3) . . ?
O6 Pr1 O7 91.2(3) 8_655 . ?
O4 Pr1 O7 137.6(2) 5_675 . ?
O2 Pr1 O7 90.7(3) 7_576 . ?
O5 Pr1 O7 65.18(19) . . ?
O3 Pr1 O7 69.9(3) 3_644 . ?
O1 Pr1 O6 140.6(2) . 2_565 ?
O6 Pr1 O6 115.7(2) 8_655 2_565 ?
O4 Pr1 O6 70.2(2) 5_675 2_565 ?
O2 Pr1 O6 82.5(2) 7_576 2_565 ?
O5 Pr1 O6 49.8(3) . 2_565 ?
O3 Pr1 O6 140.0(2) 3_644 2_565 ?
O7 Pr1 O6 75.3(2) . 2_565 ?
C10 N1 C14 117.1(11) . . ?
O6 C15 O6 128.2(15) . 2_565 ?
O6 C15 O5 115.9(7) . . ?
O6 C15 O5 115.9(7) 2_565 . ?
O6 C15 Pr1 63.2(5) . 2_565 ?
O6 C15 Pr1 168.5(10) 2_565 2_565 ?
O5 C15 Pr1 52.7(2) . 2_565 ?
C1 O1 Pr1 138.7(7) . . ?
C1 O2 Pr1 125.3(7) . 7_575 ?
C8 O3 Pr1 134.5(6) . 3_654 ?
C8 O4 Pr1 145.8(7) . 5_675 ?
C15 O5 Pr1 102.6(2) . . ?
C15 O5 Pr1 102.6(2) . 2_565 ?
Pr1 O5 Pr1 154.8(5) . 2_565 ?
C15 O6 Pr1 132.7(7) . 8_656 ?
C15 O6 Pr1 91.6(7) . 2_565 ?
Pr1 O6 Pr1 120.7(3) 8_656 2_565 ?
C9 O8 C6 119.6(9) . . ?
O2 C1 O1 124.0(10) . . ?
O2 C1 C2 117.7(9) . . ?
O1 C1 C2 118.3(9) . . ?
C7 C2 C3 119.6(8) . . ?
C7 C2 C1 119.1(8) . . ?
C3 C2 C1 121.1(8) . . ?
C4 C3 C2 119.7(8) . . ?
C5 C4 C3 120.7(9) . . ?
C5 C4 C8 119.0(9) . . ?
C3 C4 C8 120.2(8) . . ?
C4 C5 C6 119.6(9) . . ?
O8 C6 C7 117.1(8) . . ?
O8 C6 C5 122.6(9) . . ?
C7 C6 C5 120.3(8) . . ?
C2 C7 C6 120.1(8) . . ?
O4 C8 O3 124.8(9) . . ?
O4 C8 C4 116.9(8) . . ?
O3 C8 C4 118.3(9) . . ?
O8 C9 C10 111.1(10) . . ?
N1 C10 C11 124.2(11) . . ?
N1 C10 C9 116.8(12) . . ?
C11 C10 C9 119.0(12) . . ?
C12 C11 C10 117.6(12) . . ?
C13 C12 C11 118.9(12) . . ?
C14 C13 C12 119.5(12) . . ?
N1 C14 C13 122.5(12) . . ?

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
O6 C15 O5 Pr1 178.3(3) . . . . ?
O6 C15 O5 Pr1 -1.7(3) 2_565 . . . ?
Pr1 C15 O5 Pr1 180.000(1) 2_565 . . . ?
O6 C15 O5 Pr1 -1.7(3) . . . 2_565 ?
O6 C15 O5 Pr1 178.3(3) 2_565 . . 2_565 ?
O6 C15 O6 Pr1 -42.4(6) 2_565 . . 8_656 ?
O5 C15 O6 Pr1 137.6(6) . . . 8_656 ?
Pr1 C15 O6 Pr1 136.1(7) 2_565 . . 8_656 ?
O6 C15 O6 Pr1 -178.5(3) 2_565 . . 2_565 ?
O5 C15 O6 Pr1 1.5(3) . . . 2_565 ?
Pr1 O2 C1 O1 4.8(14) 7_575 . . . ?
Pr1 O2 C1 C2 -176.9(6) 7_575 . . . ?
Pr1 O1 C1 O2 -81.1(13) . . . . ?
Pr1 O1 C1 C2 100.6(11) . . . . ?
O2 C1 C2 C7 176.9(9) . . . . ?
O1 C1 C2 C7 -4.7(13) . . . . ?
O2 C1 C2 C3 1.7(14) . . . . ?
O1 C1 C2 C3 -179.9(9) . . . . ?
C7 C2 C3 C4 -0.7(14) . . . . ?
C1 C2 C3 C4 174.5(8) . . . . ?
C2 C3 C4 C5 0.5(14) . . . . ?
C2 C3 C4 C8 -175.3(9) . . . . ?
C3 C4 C5 C6 1.1(14) . . . . ?
C8 C4 C5 C6 177.0(9) . . . . ?
C9 O8 C6 C7 -123.1(13) . . . . ?
C9 O8 C6 C5 58.4(17) . . . . ?
C4 C5 C6 O8 175.8(9) . . . . ?
C4 C5 C6 C7 -2.7(15) . . . . ?
C3 C2 C7 C6 -0.9(14) . . . . ?
C1 C2 C7 C6 -176.1(9) . . . . ?
O8 C6 C7 C2 -176.0(9) . . . . ?
C5 C6 C7 C2 2.5(15) . . . . ?
Pr1 O4 C8 O3 37.9(19) 5_675 . . . ?
Pr1 O4 C8 C4 -143.5(9) 5_675 . . . ?
Pr1 O3 C8 O4 13.0(16) 3_654 . . . ?
Pr1 O3 C8 C4 -165.5(6) 3_654 . . . ?
C5 C4 C8 O4 -11.4(13) . . . . ?
C3 C4 C8 O4 164.5(9) . . . . ?
C5 C4 C8 O3 167.3(9) . . . . ?
C3 C4 C8 O3 -16.8(14) . . . . ?
C6 O8 C9 C10 -175.1(11) . . . . ?
C14 N1 C10 C11 -5.6(18) . . . . ?
C14 N1 C10 C9 176.2(11) . . . . ?
O8 C9 C10 N1 121.7(14) . . . . ?
O8 C9 C10 C11 -56.6(19) . . . . ?
N1 C10 C11 C12 4.1(19) . . . . ?
C9 C10 C11 C12 -177.7(12) . . . . ?
C10 C11 C12 C13 -1.3(19) . . . . ?
C11 C12 C13 C14 0.4(19) . . . . ?
C10 N1 C14 C13 4.4(17) . . . . ?
C12 C13 C14 N1 -2.0(19) . . . . ?

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
_geom_hbond_publ_flag
O7 H7A N1 0.85 1.93 2.695(12) 149.6 3_645 yes
O7 H7C O4 0.85 2.52 3.235(11) 142.7 6 yes

_refine_diff_density_max         1.915
_refine_diff_density_min         -1.378
_refine_diff_density_rms         0.177



