# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_ZYT_14
_database_code_depnum_ccdc_archive 'CCDC 2236703'
loop_
_audit_author_name
_audit_author_address
'Yatong Zhang'
;Shanxi University Institute of Molecular Science
China
;
_audit_update_record             
;
2023-01-17 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H13 Ce N O7, Cl'
_chemical_formula_sum            'C12 H13 Ce Cl N O7'
_chemical_formula_weight         458.80

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ce Ce -0.2486 2.6331 '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                   14.424(5)
_cell_length_b                   12.494(4)
_cell_length_c                   8.027(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.411(8)
_cell_angle_gamma                90
_cell_volume                     1440.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5325
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      28.34

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.116
_exptl_crystal_F_000             892
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    3.381
_shelx_estimated_absorpt_T_min   0.430
_shelx_estimated_absorpt_T_max   0.631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4819
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microsource'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11803
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.837
_diffrn_reflns_theta_max         28.446
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3572
_reflns_number_gt                2941
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0245P)²+5.0837P] 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         3572
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0832
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_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
Ce1 Ce 0.13971(2) 0.70105(2) 0.86550(3) 0.02495(8) Uani 1 1 d . . . . .
O1 O 0.1636(3) 0.5590(3) 0.6631(5) 0.0472(10) Uani 1 1 d . . . . .
O2 O 0.1410(3) 0.5955(3) 0.3916(5) 0.0458(9) Uani 1 1 d . . . . .
O3 O 0.0242(3) 0.3637(4) 0.2483(5) 0.0534(11) Uani 1 1 d . . . . .
O4 O -0.0388(2) 0.2492(3) 0.4108(4) 0.0339(7) Uani 1 1 d . . . . .
O5 O 0.7535(2) 0.2746(3) 0.8388(5) 0.0371(8) Uani 1 1 d . . . . .
O6 O 0.7090(2) 0.3800(3) 1.0344(5) 0.0381(8) Uani 1 1 d . . . . .
O7 O 0.1062(3) 0.5309(3) 1.0172(5) 0.0460(9) Uani 1 1 d . . . . .
H7A H 0.1218 0.4808 0.9584 0.069 Uiso 1 1 d R U . . .
H7B H 0.0914 0.5054 1.1067 0.069 Uiso 1 1 d R U . . .
C1 C 0.1577(3) 0.5345(4) 0.5136(6) 0.0282(9) Uani 1 1 d . . . . .
C2 C 0.1733(3) 0.4151(4) 0.4776(7) 0.0311(10) Uani 1 1 d . . . . .
H2 H 0.1791 0.4055 0.3579 0.037 Uiso 1 1 calc R U . . .
C3 C 0.0952(3) 0.3442(4) 0.5293(7) 0.0353(10) Uani 1 1 d . . . . .
H3A H 0.1217 0.2781 0.5757 0.042 Uiso 1 1 calc R U . . .
H3B H 0.0648 0.3801 0.6166 0.042 Uiso 1 1 calc R U . . .
C4 C 0.0235(3) 0.3181(4) 0.3867(7) 0.0347(11) Uani 1 1 d . . . . .
C5 C 0.3446(3) 0.4349(5) 0.5113(8) 0.0453(13) Uani 1 1 d . . . . .
H5A H 0.3363 0.5119 0.5132 0.054 Uiso 1 1 calc R U . . .
H5B H 0.3489 0.4136 0.3961 0.054 Uiso 1 1 calc R U . . .
C6 C 0.4340(3) 0.4064(4) 0.6139(7) 0.0345(10) Uani 1 1 d . . . . .
C7 C 0.4714(4) 0.4749(4) 0.7383(8) 0.0410(12) Uani 1 1 d . . . . .
H7 H 0.4393 0.5370 0.7616 0.049 Uiso 1 1 calc R U . . .
C8 C 0.5556(3) 0.4524(4) 0.8284(7) 0.0376(11) Uani 1 1 d . . . . .
H8 H 0.5797 0.4986 0.9124 0.045 Uiso 1 1 calc R U . . .
C9 C 0.6037(3) 0.3606(4) 0.7927(6) 0.0312(10) Uani 1 1 d . . . . .
C10 C 0.5665(3) 0.2908(4) 0.6709(7) 0.0370(11) Uani 1 1 d . . . . .
H10 H 0.5986 0.2287 0.6484 0.044 Uiso 1 1 calc R U . . .
C11 C 0.4812(4) 0.3131(4) 0.5816(8) 0.0420(12) Uani 1 1 d . . . . .
H11 H 0.4559 0.2655 0.5005 0.050 Uiso 1 1 calc R U . . .
C12 C 0.6948(3) 0.3371(4) 0.8934(6) 0.0290(9) Uani 1 1 d . . . . .
N1 N 0.2621(3) 0.3825(3) 0.5743(5) 0.0309(8) Uani 1 1 d . . . . .
H1A H 0.2597 0.3995 0.6815 0.037 Uiso 1 1 calc R U . . .
H1B H 0.2684 0.3118 0.5678 0.037 Uiso 1 1 calc R U . . .
Cl1 Cl 0.26277(12) 0.14545(12) 0.4772(2) 0.0577(4) 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
Ce1 O1 2.452(4) . ?
Ce1 O6 2.470(3) 3_667 ?
Ce1 O4 2.489(3) 2_556 ?
Ce1 O7 2.520(3) . ?
Ce1 O5 2.526(4) 2_656 ?
Ce1 O2 2.550(4) 4_576 ?
Ce1 O3 2.582(4) 3_566 ?
Ce1 O4 2.611(4) 3_566 ?
Ce1 O5 2.722(4) 3_667 ?
Ce1 C4 2.966(5) 3_566 ?
Ce1 C12 2.967(5) 3_667 ?
O1 C1 1.234(6) . ?
O2 C1 1.247(6) . ?
O2 Ce1 2.550(4) 4_575 ?
O3 C4 1.250(6) . ?
O3 Ce1 2.582(4) 3_566 ?
O4 C4 1.273(6) . ?
O4 Ce1 2.489(3) 2_546 ?
O4 Ce1 2.610(4) 3_566 ?
O5 C12 1.261(6) . ?
O5 Ce1 2.526(4) 2_646 ?
O5 Ce1 2.722(4) 3_667 ?
O6 C12 1.252(6) . ?
O6 Ce1 2.470(3) 3_667 ?
O7 H7A 0.8280 . ?
O7 H7B 0.8313 . ?
C1 C2 1.540(6) . ?
C2 N1 1.490(6) . ?
C2 C3 1.522(7) . ?
C2 H2 0.9800 . ?
C3 C4 1.504(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 Ce1 2.966(5) 3_566 ?
C5 N1 1.488(6) . ?
C5 C6 1.506(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C11 1.386(7) . ?
C6 C7 1.386(8) . ?
C7 C8 1.383(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.385(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(7) . ?
C9 C12 1.505(6) . ?
C10 C11 1.393(7) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 Ce1 2.967(5) 3_667 ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?

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 Ce1 O6 75.15(13) . 3_667 ?
O1 Ce1 O4 141.36(13) . 2_556 ?
O6 Ce1 O4 115.02(12) 3_667 2_556 ?
O1 Ce1 O7 75.82(14) . . ?
O6 Ce1 O7 72.58(13) 3_667 . ?
O4 Ce1 O7 72.74(13) 2_556 . ?
O1 Ce1 O5 72.58(13) . 2_656 ?
O6 Ce1 O5 77.67(12) 3_667 2_656 ?
O4 Ce1 O5 144.50(12) 2_556 2_656 ?
O7 Ce1 O5 141.00(13) . 2_656 ?
O1 Ce1 O2 140.83(13) . 4_576 ?
O6 Ce1 O2 112.50(13) 3_667 4_576 ?
O4 Ce1 O2 72.56(12) 2_556 4_576 ?
O7 Ce1 O2 143.28(13) . 4_576 ?
O5 Ce1 O2 71.99(12) 2_656 4_576 ?
O1 Ce1 O3 73.75(15) . 3_566 ?
O6 Ce1 O3 137.52(14) 3_667 3_566 ?
O4 Ce1 O3 75.69(13) 2_556 3_566 ?
O7 Ce1 O3 72.27(13) . 3_566 ?
O5 Ce1 O3 118.56(12) 2_656 3_566 ?
O2 Ce1 O3 109.91(14) 4_576 3_566 ?
O1 Ce1 O4 73.22(12) . 3_566 ?
O6 Ce1 O4 141.12(11) 3_667 3_566 ?
O4 Ce1 O4 103.80(11) 2_556 3_566 ?
O7 Ce1 O4 119.65(12) . 3_566 ?
O5 Ce1 O4 71.75(11) 2_656 3_566 ?
O2 Ce1 O4 80.30(12) 4_576 3_566 ?
O3 Ce1 O4 49.91(12) 3_566 3_566 ?
O1 Ce1 O5 123.74(12) . 3_667 ?
O6 Ce1 O5 49.64(11) 3_667 3_667 ?
O4 Ce1 O5 70.44(11) 2_556 3_667 ?
O7 Ce1 O5 77.97(12) . 3_667 ?
O5 Ce1 O5 101.30(11) 2_656 3_667 ?
O2 Ce1 O5 79.50(12) 4_576 3_667 ?
O3 Ce1 O5 140.10(12) 3_566 3_667 ?
O4 Ce1 O5 159.79(11) 3_566 3_667 ?
O1 Ce1 C4 69.00(14) . 3_566 ?
O6 Ce1 C4 143.98(13) 3_667 3_566 ?
O4 Ce1 C4 91.81(13) 2_556 3_566 ?
O7 Ce1 C4 94.92(14) . 3_566 ?
O5 Ce1 C4 94.55(13) 2_656 3_566 ?
O2 Ce1 C4 97.78(14) 4_576 3_566 ?
O3 Ce1 C4 24.82(13) 3_566 3_566 ?
O4 Ce1 C4 25.36(12) 3_566 3_566 ?
O5 Ce1 C4 162.09(13) 3_667 3_566 ?
O1 Ce1 C12 99.28(14) . 3_667 ?
O6 Ce1 C12 24.52(12) 3_667 3_667 ?
O4 Ce1 C12 93.29(12) 2_556 3_667 ?
O7 Ce1 C12 74.25(13) . 3_667 ?
O5 Ce1 C12 88.83(12) 2_656 3_667 ?
O2 Ce1 C12 96.16(13) 4_576 3_667 ?
O3 Ce1 C12 146.50(13) 3_566 3_667 ?
O4 Ce1 C12 160.45(12) 3_566 3_667 ?
O5 Ce1 C12 25.13(12) 3_667 3_667 ?
C4 Ce1 C12 166.02(14) 3_566 3_667 ?
C1 O1 Ce1 145.4(3) . . ?
C1 O2 Ce1 132.3(3) . 4_575 ?
C4 O3 Ce1 95.0(3) . 3_566 ?
C4 O4 Ce1 138.0(3) . 2_546 ?
C4 O4 Ce1 93.1(3) . 3_566 ?
Ce1 O4 Ce1 110.71(12) 2_546 3_566 ?
C12 O5 Ce1 157.1(3) . 2_646 ?
C12 O5 Ce1 88.4(3) . 3_667 ?
Ce1 O5 Ce1 106.10(12) 2_646 3_667 ?
C12 O6 Ce1 100.6(3) . 3_667 ?
Ce1 O7 H7A 106.7 . . ?
Ce1 O7 H7B 144.8 . . ?
H7A O7 H7B 107.9 . . ?
O1 C1 O2 127.1(4) . . ?
O1 C1 C2 115.2(4) . . ?
O2 C1 C2 117.8(4) . . ?
N1 C2 C3 108.7(4) . . ?
N1 C2 C1 107.5(4) . . ?
C3 C2 C1 112.8(4) . . ?
N1 C2 H2 109.2 . . ?
C3 C2 H2 109.2 . . ?
C1 C2 H2 109.2 . . ?
C4 C3 C2 113.1(4) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
O3 C4 O4 120.6(5) . . ?
O3 C4 C3 121.0(4) . . ?
O4 C4 C3 118.4(5) . . ?
O3 C4 Ce1 60.1(3) . 3_566 ?
O4 C4 Ce1 61.5(3) . 3_566 ?
C3 C4 Ce1 168.9(4) . 3_566 ?
N1 C5 C6 112.4(4) . . ?
N1 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N1 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C11 C6 C7 119.4(5) . . ?
C11 C6 C5 120.5(5) . . ?
C7 C6 C5 120.1(5) . . ?
C8 C7 C6 120.9(5) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 119.5(5) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 120.1(5) . . ?
C10 C9 C12 121.2(4) . . ?
C8 C9 C12 118.7(5) . . ?
C9 C10 C11 120.2(5) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C6 C11 C10 119.8(5) . . ?
C6 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
O6 C12 O5 121.4(4) . . ?
O6 C12 C9 117.5(4) . . ?
O5 C12 C9 121.1(5) . . ?
O6 C12 Ce1 54.9(2) . 3_667 ?
O5 C12 Ce1 66.5(3) . 3_667 ?
C9 C12 Ce1 171.7(3) . 3_667 ?
C5 N1 C2 112.2(4) . . ?
C5 N1 H1A 109.2 . . ?
C2 N1 H1A 109.2 . . ?
C5 N1 H1B 109.2 . . ?
C2 N1 H1B 109.2 . . ?
H1A N1 H1B 107.9 . . ?

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
Ce1 O1 C1 O2 9.4(10) . . . . ?
Ce1 O1 C1 C2 -170.9(4) . . . . ?
Ce1 O2 C1 O1 13.1(8) 4_575 . . . ?
Ce1 O2 C1 C2 -166.6(3) 4_575 . . . ?
O1 C1 C2 N1 -50.9(6) . . . . ?
O2 C1 C2 N1 128.8(5) . . . . ?
O1 C1 C2 C3 69.0(6) . . . . ?
O2 C1 C2 C3 -111.3(5) . . . . ?
N1 C2 C3 C4 -144.1(4) . . . . ?
C1 C2 C3 C4 96.7(5) . . . . ?
Ce1 O3 C4 O4 12.0(5) 3_566 . . . ?
Ce1 O3 C4 C3 -167.1(4) 3_566 . . . ?
Ce1 O4 C4 O3 -137.9(5) 2_546 . . . ?
Ce1 O4 C4 O3 -11.8(5) 3_566 . . . ?
Ce1 O4 C4 C3 41.2(7) 2_546 . . . ?
Ce1 O4 C4 C3 167.3(4) 3_566 . . . ?
Ce1 O4 C4 Ce1 -126.1(4) 2_546 . . 3_566 ?
C2 C3 C4 O3 -9.2(7) . . . . ?
C2 C3 C4 O4 171.7(4) . . . . ?
C2 C3 C4 Ce1 -101.7(18) . . . 3_566 ?
N1 C5 C6 C11 84.4(7) . . . . ?
N1 C5 C6 C7 -97.5(6) . . . . ?
C11 C6 C7 C8 1.1(9) . . . . ?
C5 C6 C7 C8 -177.0(5) . . . . ?
C6 C7 C8 C9 0.6(9) . . . . ?
C7 C8 C9 C10 -1.7(8) . . . . ?
C7 C8 C9 C12 -179.4(5) . . . . ?
C8 C9 C10 C11 1.0(8) . . . . ?
C12 C9 C10 C11 178.7(5) . . . . ?
C7 C6 C11 C10 -1.8(8) . . . . ?
C5 C6 C11 C10 176.3(5) . . . . ?
C9 C10 C11 C6 0.8(9) . . . . ?
Ce1 O6 C12 O5 -2.4(5) 3_667 . . . ?
Ce1 O6 C12 C9 176.1(3) 3_667 . . . ?
Ce1 O5 C12 O6 -128.1(7) 2_646 . . . ?
Ce1 O5 C12 O6 2.2(5) 3_667 . . . ?
Ce1 O5 C12 C9 53.5(10) 2_646 . . . ?
Ce1 O5 C12 C9 -176.3(4) 3_667 . . . ?
Ce1 O5 C12 Ce1 -130.3(8) 2_646 . . 3_667 ?
C10 C9 C12 O6 -155.7(5) . . . . ?
C8 C9 C12 O6 22.0(7) . . . . ?
C10 C9 C12 O5 22.8(7) . . . . ?
C8 C9 C12 O5 -159.5(5) . . . . ?
C6 C5 N1 C2 177.2(4) . . . . ?
C3 C2 N1 C5 170.3(4) . . . . ?
C1 C2 N1 C5 -67.3(5) . . . . ?

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
N1 H1A Cl1 0.89 2.44 3.252(5) 152.6 4_566
N1 H1B Cl1 0.89 2.20 3.063(4) 162.9 .
O7 H7A Cl1 0.83 2.57 3.193(4) 133.4 4_566
O7 H7B O2 0.83 2.59 3.106(6) 121.6 1_556
O7 H7B O3 0.83 2.36 3.101(5) 148.6 1_556

_refine_diff_density_max         1.042
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.137



####################################################################### 
# 
# 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_ZYT_17
_database_code_depnum_ccdc_archive 'CCDC 2236705'
loop_
_audit_author_name
_audit_author_address
'Yatong Zhang'
;Shanxi University Institute of Molecular Science
China
;
_audit_update_record             
;
2023-01-17 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H13 N Nd O7, Cl'
_chemical_formula_sum            'C12 H13 Cl N Nd O7'
_chemical_formula_weight         462.92

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'
Cl Cl 0.1484 0.1585 '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'

_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                   14.441(6)
_cell_length_b                   12.511(5)
_cell_length_c                   7.996(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.595(10)
_cell_angle_gamma                90
_cell_volume                     1437.8(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2697
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      28.32

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.139
_exptl_crystal_F_000             900
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    3.831
_shelx_estimated_absorpt_T_min   0.393
_shelx_estimated_absorpt_T_max   0.597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4483
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microsource'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7649
_diffrn_reflns_av_unetI/netI     0.0812
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.834
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.954
_reflns_number_total             2550
_reflns_number_gt                1864
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0296P)²+28.0308P] 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         2550
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1452
_refine_ls_wR_factor_gt          0.1236
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_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
Nd1 Nd 0.13926(4) 0.70140(5) 0.86523(8) 0.0265(2) Uani 1 1 d . . . . .
O1 O 0.1625(7) 0.5598(7) 0.6667(12) 0.046(2) Uani 1 1 d . . . . .
O2 O 0.1418(7) 0.5961(8) 0.3938(12) 0.052(3) Uani 1 1 d . . . . .
O3 O 0.0236(7) 0.3630(9) 0.2489(14) 0.056(3) Uani 1 1 d . . . . .
O4 O -0.0402(6) 0.2483(7) 0.4090(11) 0.035(2) Uani 1 1 d . . . . .
O5 O 0.7543(6) 0.2730(7) 0.8404(12) 0.040(2) Uani 1 1 d . . . . .
O6 O 0.7111(6) 0.3792(8) 1.0358(12) 0.042(2) Uani 1 1 d . . . . .
O7 O 0.1051(6) 0.5339(7) 1.0168(12) 0.046(2) Uani 1 1 d . . . . .
H7A H 0.1207 0.4838 0.9579 0.069 Uiso 1 1 d R U . . .
H7B H 0.0904 0.5084 1.1062 0.069 Uiso 1 1 d R U . . .
C1 C 0.1556(8) 0.5356(10) 0.5163(17) 0.034(3) Uani 1 1 d . . . . .
C2 C 0.1725(8) 0.4170(9) 0.4795(17) 0.031(3) Uani 1 1 d . . . . .
H2 H 0.1784 0.4084 0.3592 0.038 Uiso 1 1 calc R U . . .
C3 C 0.0930(9) 0.3439(11) 0.5295(18) 0.041(3) Uani 1 1 d . . . . .
H3A H 0.1199 0.2784 0.5774 0.049 Uiso 1 1 calc R U . . .
H3B H 0.0617 0.3795 0.6160 0.049 Uiso 1 1 calc R U . . .
C4 C 0.0221(9) 0.3158(11) 0.3865(17) 0.039(3) Uani 1 1 d . . . . .
C5 C 0.3451(8) 0.4377(12) 0.5119(19) 0.041(4) Uani 1 1 d . . . . .
H5A H 0.3495 0.4176 0.3958 0.050 Uiso 1 1 calc R U . . .
H5B H 0.3373 0.5146 0.5162 0.050 Uiso 1 1 calc R U . . .
C6 C 0.4331(8) 0.4069(12) 0.6153(17) 0.040(3) Uani 1 1 d . . . . .
C7 C 0.4715(8) 0.4736(11) 0.7393(18) 0.037(3) Uani 1 1 d . . . . .
H7 H 0.4396 0.5351 0.7646 0.045 Uiso 1 1 calc R U . . .
C8 C 0.5563(8) 0.4519(11) 0.8278(19) 0.039(3) Uani 1 1 d . . . . .
H8 H 0.5814 0.4985 0.9108 0.047 Uiso 1 1 calc R U . . .
C9 C 0.6034(8) 0.3606(10) 0.7919(16) 0.029(3) Uani 1 1 d . . . . .
C10 C 0.5660(9) 0.2909(12) 0.6714(18) 0.042(3) Uani 1 1 d . . . . .
H10 H 0.5978 0.2288 0.6488 0.051 Uiso 1 1 calc R U . . .
C11 C 0.4788(9) 0.3134(12) 0.5815(17) 0.042(3) Uani 1 1 d . . . . .
H11 H 0.4526 0.2660 0.5008 0.050 Uiso 1 1 calc R U . . .
C12 C 0.6958(8) 0.3370(9) 0.8950(17) 0.029(3) Uani 1 1 d . . . . .
N1 N 0.2605(7) 0.3831(8) 0.5754(14) 0.035(3) Uani 1 1 d . . . . .
H1A H 0.2665 0.3126 0.5667 0.042 Uiso 1 1 calc R U . . .
H1B H 0.2582 0.3989 0.6835 0.042 Uiso 1 1 calc R U . . .
Cl1 Cl 0.2617(3) 0.1451(3) 0.4816(6) 0.0570(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
Nd1 O1 2.424(9) . ?
Nd1 O6 2.445(9) 3_667 ?
Nd1 O4 2.481(9) 2_556 ?
Nd1 O7 2.494(9) . ?
Nd1 O5 2.523(9) 2_656 ?
Nd1 O2 2.543(10) 4_576 ?
Nd1 O3 2.568(10) 3_566 ?
Nd1 O4 2.577(9) 3_566 ?
Nd1 O5 2.702(9) 3_667 ?
Nd1 C4 2.934(13) 3_566 ?
Nd1 C12 2.947(13) 3_667 ?
O1 C1 1.234(15) . ?
O2 C1 1.239(15) . ?
O2 Nd1 2.543(10) 4_575 ?
O3 C4 1.251(16) . ?
O3 Nd1 2.568(10) 3_566 ?
O4 C4 1.259(16) . ?
O4 Nd1 2.481(9) 2_546 ?
O4 Nd1 2.577(9) 3_566 ?
O5 C12 1.271(14) . ?
O5 Nd1 2.523(9) 2_646 ?
O5 Nd1 2.702(9) 3_667 ?
O6 C12 1.243(16) . ?
O6 Nd1 2.445(9) 3_667 ?
O7 H7A 0.8280 . ?
O7 H7B 0.8297 . ?
C1 C2 1.536(17) . ?
C2 N1 1.480(14) . ?
C2 C3 1.551(17) . ?
C2 H2 0.9800 . ?
C3 C4 1.501(18) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 Nd1 2.934(13) 3_566 ?
C5 C6 1.496(16) . ?
C5 N1 1.529(15) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.371(19) . ?
C6 C11 1.383(19) . ?
C7 C8 1.381(17) . ?
C7 H7 0.9300 . ?
C8 C9 1.373(17) . ?
C8 H8 0.9300 . ?
C9 C10 1.370(18) . ?
C9 C12 1.528(16) . ?
C10 C11 1.416(18) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 Nd1 2.947(13) 3_667 ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?

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 Nd1 O6 74.7(3) . 3_667 ?
O1 Nd1 O4 140.9(3) . 2_556 ?
O6 Nd1 O4 114.6(3) 3_667 2_556 ?
O1 Nd1 O7 75.6(3) . . ?
O6 Nd1 O7 72.9(3) 3_667 . ?
O4 Nd1 O7 71.9(3) 2_556 . ?
O1 Nd1 O5 72.6(3) . 2_656 ?
O6 Nd1 O5 77.4(3) 3_667 2_656 ?
O4 Nd1 O5 145.3(3) 2_556 2_656 ?
O7 Nd1 O5 141.0(3) . 2_656 ?
O1 Nd1 O2 141.7(3) . 4_576 ?
O6 Nd1 O2 112.1(3) 3_667 4_576 ?
O4 Nd1 O2 72.8(3) 2_556 4_576 ?
O7 Nd1 O2 142.7(3) . 4_576 ?
O5 Nd1 O2 72.6(3) 2_656 4_576 ?
O1 Nd1 O3 73.6(4) . 3_566 ?
O6 Nd1 O3 137.3(3) 3_667 3_566 ?
O4 Nd1 O3 76.1(3) 2_556 3_566 ?
O7 Nd1 O3 72.0(3) . 3_566 ?
O5 Nd1 O3 118.4(3) 2_656 3_566 ?
O2 Nd1 O3 110.5(4) 4_576 3_566 ?
O1 Nd1 O4 73.9(3) . 3_566 ?
O6 Nd1 O4 140.9(3) 3_667 3_566 ?
O4 Nd1 O4 104.4(3) 2_556 3_566 ?
O7 Nd1 O4 119.9(3) . 3_566 ?
O5 Nd1 O4 71.4(3) 2_656 3_566 ?
O2 Nd1 O4 80.5(3) 4_576 3_566 ?
O3 Nd1 O4 50.3(3) 3_566 3_566 ?
O1 Nd1 O5 123.6(3) . 3_667 ?
O6 Nd1 O5 50.0(3) 3_667 3_667 ?
O4 Nd1 O5 70.0(3) 2_556 3_667 ?
O7 Nd1 O5 78.4(3) . 3_667 ?
O5 Nd1 O5 101.2(3) 2_656 3_667 ?
O2 Nd1 O5 78.6(3) 4_576 3_667 ?
O3 Nd1 O5 140.4(3) 3_566 3_667 ?
O4 Nd1 O5 159.1(3) 3_566 3_667 ?
O1 Nd1 C4 69.4(3) . 3_566 ?
O6 Nd1 C4 144.0(3) 3_667 3_566 ?
O4 Nd1 C4 92.3(3) 2_556 3_566 ?
O7 Nd1 C4 95.2(4) . 3_566 ?
O5 Nd1 C4 94.2(3) 2_656 3_566 ?
O2 Nd1 C4 97.9(4) 4_576 3_566 ?
O3 Nd1 C4 25.2(3) 3_566 3_566 ?
O4 Nd1 C4 25.4(3) 3_566 3_566 ?
O5 Nd1 C4 162.3(3) 3_667 3_566 ?
O1 Nd1 C12 98.7(3) . 3_667 ?
O6 Nd1 C12 24.5(3) 3_667 3_667 ?
O4 Nd1 C12 93.0(3) 2_556 3_667 ?
O7 Nd1 C12 74.5(3) . 3_667 ?
O5 Nd1 C12 88.7(3) 2_656 3_667 ?
O2 Nd1 C12 95.8(3) 4_576 3_667 ?
O3 Nd1 C12 146.5(3) 3_566 3_667 ?
O4 Nd1 C12 160.0(3) 3_566 3_667 ?
O5 Nd1 C12 25.5(3) 3_667 3_667 ?
C4 Nd1 C12 166.2(4) 3_566 3_667 ?
C1 O1 Nd1 144.5(9) . . ?
C1 O2 Nd1 132.8(9) . 4_575 ?
C4 O3 Nd1 94.0(8) . 3_566 ?
C4 O4 Nd1 137.2(8) . 2_546 ?
C4 O4 Nd1 93.4(7) . 3_566 ?
Nd1 O4 Nd1 111.4(3) 2_546 3_566 ?
C12 O5 Nd1 156.2(9) . 2_646 ?
C12 O5 Nd1 88.1(8) . 3_667 ?
Nd1 O5 Nd1 106.2(3) 2_646 3_667 ?
C12 O6 Nd1 101.0(8) . 3_667 ?
Nd1 O7 H7A 106.4 . . ?
Nd1 O7 H7B 145.2 . . ?
H7A O7 H7B 107.8 . . ?
O1 C1 O2 127.7(13) . . ?
O1 C1 C2 115.1(12) . . ?
O2 C1 C2 117.1(12) . . ?
N1 C2 C1 108.8(10) . . ?
N1 C2 C3 108.5(10) . . ?
C1 C2 C3 112.6(11) . . ?
N1 C2 H2 109.0 . . ?
C1 C2 H2 109.0 . . ?
C3 C2 H2 109.0 . . ?
C4 C3 C2 114.2(12) . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
O3 C4 O4 121.1(12) . . ?
O3 C4 C3 119.4(13) . . ?
O4 C4 C3 119.4(12) . . ?
O3 C4 Nd1 60.8(7) . 3_566 ?
O4 C4 Nd1 61.2(6) . 3_566 ?
C3 C4 Nd1 167.7(9) . 3_566 ?
C6 C5 N1 111.4(10) . . ?
C6 C5 H5A 109.3 . . ?
N1 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
N1 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C7 C6 C11 119.2(11) . . ?
C7 C6 C5 120.4(13) . . ?
C11 C6 C5 120.4(13) . . ?
C6 C7 C8 121.8(12) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C9 C8 C7 119.3(13) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 120.4(12) . . ?
C10 C9 C12 121.4(12) . . ?
C8 C9 C12 118.1(11) . . ?
C9 C10 C11 120.0(13) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C6 C11 C10 119.2(13) . . ?
C6 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
O6 C12 O5 120.9(12) . . ?
O6 C12 C9 118.4(11) . . ?
O5 C12 C9 120.7(12) . . ?
O6 C12 Nd1 54.5(6) . 3_667 ?
O5 C12 Nd1 66.4(7) . 3_667 ?
C9 C12 Nd1 172.1(9) . 3_667 ?
C2 N1 C5 112.0(9) . . ?
C2 N1 H1A 109.2 . . ?
C5 N1 H1A 109.2 . . ?
C2 N1 H1B 109.2 . . ?
C5 N1 H1B 109.2 . . ?
H1A N1 H1B 107.9 . . ?

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 O1 C1 O2 13(3) . . . . ?
Nd1 O1 C1 C2 -171.7(10) . . . . ?
Nd1 O2 C1 O1 9(2) 4_575 . . . ?
Nd1 O2 C1 C2 -166.9(8) 4_575 . . . ?
O1 C1 C2 N1 -49.7(15) . . . . ?
O2 C1 C2 N1 126.5(12) . . . . ?
O1 C1 C2 C3 70.6(14) . . . . ?
O2 C1 C2 C3 -113.2(14) . . . . ?
N1 C2 C3 C4 -142.3(11) . . . . ?
C1 C2 C3 C4 97.2(13) . . . . ?
Nd1 O3 C4 O4 11.2(14) 3_566 . . . ?
Nd1 O3 C4 C3 -165.9(11) 3_566 . . . ?
Nd1 O4 C4 O3 -138.1(11) 2_546 . . . ?
Nd1 O4 C4 O3 -11.1(14) 3_566 . . . ?
Nd1 O4 C4 C3 38.9(18) 2_546 . . . ?
Nd1 O4 C4 C3 165.9(11) 3_566 . . . ?
Nd1 O4 C4 Nd1 -127.0(11) 2_546 . . 3_566 ?
C2 C3 C4 O3 -10.1(18) . . . . ?
C2 C3 C4 O4 172.8(11) . . . . ?
C2 C3 C4 Nd1 -97(5) . . . 3_566 ?
N1 C5 C6 C7 -99.1(16) . . . . ?
N1 C5 C6 C11 83.9(16) . . . . ?
C11 C6 C7 C8 2(2) . . . . ?
C5 C6 C7 C8 -174.7(13) . . . . ?
C6 C7 C8 C9 -1(2) . . . . ?
C7 C8 C9 C10 -1(2) . . . . ?
C7 C8 C9 C12 -178.3(12) . . . . ?
C8 C9 C10 C11 1(2) . . . . ?
C12 C9 C10 C11 178.1(12) . . . . ?
C7 C6 C11 C10 -2(2) . . . . ?
C5 C6 C11 C10 174.5(13) . . . . ?
C9 C10 C11 C6 1(2) . . . . ?
Nd1 O6 C12 O5 -1.7(13) 3_667 . . . ?
Nd1 O6 C12 C9 176.0(9) 3_667 . . . ?
Nd1 O5 C12 O6 -126.5(18) 2_646 . . . ?
Nd1 O5 C12 O6 1.5(12) 3_667 . . . ?
Nd1 O5 C12 C9 56(2) 2_646 . . . ?
Nd1 O5 C12 C9 -176.1(10) 3_667 . . . ?
Nd1 O5 C12 Nd1 -128.0(19) 2_646 . . 3_667 ?
C10 C9 C12 O6 -155.1(13) . . . . ?
C8 C9 C12 O6 22.2(18) . . . . ?
C10 C9 C12 O5 22.5(19) . . . . ?
C8 C9 C12 O5 -160.2(12) . . . . ?
C1 C2 N1 C5 -67.2(14) . . . . ?
C3 C2 N1 C5 170.0(11) . . . . ?
C6 C5 N1 C2 177.2(12) . . . . ?

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 H7B O3 0.83 2.40 3.135(14) 148.3 1_556
O7 H7B O2 0.83 2.59 3.108(14) 121.8 1_556
O7 H7A Cl1 0.83 2.59 3.213(10) 133.3 4_566
N1 H1A Cl1 0.89 2.20 3.072(11) 165.2 .
N1 H1B Cl1 0.89 2.44 3.265(12) 154.0 4_566

_refine_diff_density_max         2.245
_refine_diff_density_min         -1.790
_refine_diff_density_rms         0.230



####################################################################### 
# 
# 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_ZYT_16
_database_code_depnum_ccdc_archive 'CCDC 2236704'
loop_
_audit_author_name
_audit_author_address
'Yatong Zhang'
;Shanxi University Institute of Molecular Science
China
;
_audit_update_record             
;
2023-01-17 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H13 N O7 Pr, Cl'
_chemical_formula_sum            'C12 H13 Cl N O7 Pr'
_chemical_formula_weight         459.59

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pr Pr -0.2180 2.8214 '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                   14.3677(19)
_cell_length_b                   12.4449(18)
_cell_length_c                   7.9612(14)
_cell_angle_alpha                90
_cell_angle_beta                 95.443(5)
_cell_angle_gamma                90
_cell_volume                     1417.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1443
_cell_measurement_theta_min      3.26
_cell_measurement_theta_max      28.10


_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.154
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    3.661
_shelx_estimated_absorpt_T_min   0.406
_shelx_estimated_absorpt_T_max   0.610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5082
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microsource'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13310
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.848
_diffrn_reflns_theta_max         28.444
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3538
_reflns_number_gt                2835
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0181P)²+5.1463P] 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         3538
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0812
_refine_ls_wR_factor_gt          0.0755
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
Pr1 Pr 0.13960(2) 0.70121(2) 0.86570(3) 0.02335(8) Uani 1 1 d . . . . .
O1 O 0.1632(3) 0.5589(3) 0.6654(5) 0.0461(10) Uani 1 1 d . . . . .
O2 O 0.1412(3) 0.5961(3) 0.3922(5) 0.0452(10) Uani 1 1 d . . . . .
O3 O 0.0236(3) 0.3636(4) 0.2470(5) 0.0537(12) Uani 1 1 d . . . . .
O4 O -0.0398(2) 0.2489(3) 0.4096(4) 0.0311(7) Uani 1 1 d . . . . .
O5 O 0.7541(2) 0.2735(3) 0.8388(5) 0.0355(8) Uani 1 1 d . . . . .
O6 O 0.7100(3) 0.3795(3) 1.0358(5) 0.0367(8) Uani 1 1 d . . . . .
O7 O 0.1063(3) 0.5321(3) 1.0180(5) 0.0437(10) Uani 1 1 d . . . . .
H7A H 0.1218 0.4820 0.9592 0.066 Uiso 1 1 d R U . . .
H7B H 0.0915 0.5066 1.1075 0.066 Uiso 1 1 d R U . . .
C1 C 0.1578(3) 0.5351(4) 0.5142(6) 0.0272(10) Uani 1 1 d . . . . .
C2 C 0.1728(3) 0.4154(4) 0.4774(7) 0.0299(10) Uani 1 1 d . . . . .
H2 H 0.1785 0.4059 0.3567 0.036 Uiso 1 1 calc R U . . .
C3 C 0.0943(4) 0.3439(4) 0.5297(7) 0.0346(11) Uani 1 1 d . . . . .
H3A H 0.1210 0.2774 0.5762 0.041 Uiso 1 1 calc R U . . .
H3B H 0.0637 0.3797 0.6177 0.041 Uiso 1 1 calc R U . . .
C4 C 0.0231(3) 0.3180(4) 0.3862(7) 0.0326(11) Uani 1 1 d . . . . .
C5 C 0.3445(3) 0.4357(5) 0.5117(8) 0.0419(14) Uani 1 1 d . . . . .
H5A H 0.3364 0.5130 0.5145 0.050 Uiso 1 1 calc R U . . .
H5B H 0.3486 0.4147 0.3952 0.050 Uiso 1 1 calc R U . . .
C6 C 0.4340(3) 0.4064(4) 0.6140(7) 0.0331(11) Uani 1 1 d . . . . .
C7 C 0.4710(4) 0.4747(5) 0.7382(8) 0.0416(13) Uani 1 1 d . . . . .
H7 H 0.4388 0.5368 0.7620 0.050 Uiso 1 1 calc R U . . .
C8 C 0.5557(4) 0.4518(4) 0.8281(7) 0.0374(12) Uani 1 1 d . . . . .
H8 H 0.5800 0.4980 0.9130 0.045 Uiso 1 1 calc R U . . .
C9 C 0.6039(3) 0.3603(4) 0.7917(7) 0.0293(10) Uani 1 1 d . . . . .
C10 C 0.5665(4) 0.2902(4) 0.6708(7) 0.0369(12) Uani 1 1 d . . . . .
H10 H 0.5983 0.2275 0.6484 0.044 Uiso 1 1 calc R U . . .
C11 C 0.4807(4) 0.3130(5) 0.5815(8) 0.0383(12) Uani 1 1 d . . . . .
H11 H 0.4549 0.2652 0.5001 0.046 Uiso 1 1 calc R U . . .
C12 C 0.6952(3) 0.3371(4) 0.8933(7) 0.0292(10) Uani 1 1 d . . . . .
N1 N 0.2619(3) 0.3829(3) 0.5750(5) 0.0301(9) Uani 1 1 d . . . . .
H1A H 0.2595 0.4000 0.6830 0.036 Uiso 1 1 calc R U . . .
H1B H 0.2684 0.3119 0.5686 0.036 Uiso 1 1 calc R U . . .
Cl1 Cl 0.26221(13) 0.14463(12) 0.4801(2) 0.0558(4) 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
Pr1 O1 2.429(4) . ?
Pr1 O6 2.444(4) 3_667 ?
Pr1 O4 2.469(3) 2_556 ?
Pr1 O7 2.498(4) . ?
Pr1 O5 2.503(4) 2_656 ?
Pr1 O2 2.531(4) 4_576 ?
Pr1 O3 2.560(4) 3_566 ?
Pr1 O4 2.579(4) 3_566 ?
Pr1 O5 2.698(4) 3_667 ?
Pr1 C4 2.941(5) 3_566 ?
Pr1 C12 2.946(5) 3_667 ?
O1 C1 1.234(6) . ?
O2 C1 1.239(6) . ?
O2 Pr1 2.531(4) 4_575 ?
O3 C4 1.246(7) . ?
O3 Pr1 2.560(4) 3_566 ?
O4 C4 1.273(6) . ?
O4 Pr1 2.469(3) 2_546 ?
O4 Pr1 2.579(4) 3_566 ?
O5 C12 1.265(6) . ?
O5 Pr1 2.503(4) 2_646 ?
O5 Pr1 2.699(4) 3_667 ?
O6 C12 1.252(6) . ?
O6 Pr1 2.444(4) 3_667 ?
O7 H7A 0.8236 . ?
O7 H7B 0.8255 . ?
C1 C2 1.537(6) . ?
C2 N1 1.490(6) . ?
C2 C3 1.524(7) . ?
C2 H2 0.9800 . ?
C3 C4 1.495(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 Pr1 2.941(5) 3_566 ?
C5 N1 1.486(6) . ?
C5 C6 1.500(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.373(8) . ?
C6 C11 1.378(7) . ?
C7 C8 1.381(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.379(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(7) . ?
C9 C12 1.502(7) . ?
C10 C11 1.393(8) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 Pr1 2.946(5) 3_667 ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?

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 74.72(14) . 3_667 ?
O1 Pr1 O4 141.09(13) . 2_556 ?
O6 Pr1 O4 115.04(12) 3_667 2_556 ?
O1 Pr1 O7 75.50(14) . . ?
O6 Pr1 O7 72.69(13) 3_667 . ?
O4 Pr1 O7 72.52(13) 2_556 . ?
O1 Pr1 O5 72.72(13) . 2_656 ?
O6 Pr1 O5 77.34(12) 3_667 2_656 ?
O4 Pr1 O5 144.79(12) 2_556 2_656 ?
O7 Pr1 O5 140.86(13) . 2_656 ?
O1 Pr1 O2 141.33(13) . 4_576 ?
O6 Pr1 O2 112.46(13) 3_667 4_576 ?
O4 Pr1 O2 72.62(12) 2_556 4_576 ?
O7 Pr1 O2 143.11(13) . 4_576 ?
O5 Pr1 O2 72.23(12) 2_656 4_576 ?
O1 Pr1 O3 73.75(16) . 3_566 ?
O6 Pr1 O3 137.34(15) 3_667 3_566 ?
O4 Pr1 O3 75.77(13) 2_556 3_566 ?
O7 Pr1 O3 72.13(14) . 3_566 ?
O5 Pr1 O3 118.70(13) 2_656 3_566 ?
O2 Pr1 O3 110.14(15) 4_576 3_566 ?
O1 Pr1 O4 73.64(13) . 3_566 ?
O6 Pr1 O4 140.81(12) 3_667 3_566 ?
O4 Pr1 O4 104.10(12) 2_556 3_566 ?
O7 Pr1 O4 119.91(13) . 3_566 ?
O5 Pr1 O4 71.63(11) 2_656 3_566 ?
O2 Pr1 O4 80.27(12) 4_576 3_566 ?
O3 Pr1 O4 50.28(12) 3_566 3_566 ?
O1 Pr1 O5 123.70(12) . 3_667 ?
O6 Pr1 O5 50.09(11) 3_667 3_667 ?
O4 Pr1 O5 70.11(11) 2_556 3_667 ?
O7 Pr1 O5 78.10(13) . 3_667 ?
O5 Pr1 O5 101.28(11) 2_656 3_667 ?
O2 Pr1 O5 79.11(12) 4_576 3_667 ?
O3 Pr1 O5 139.99(12) 3_566 3_667 ?
O4 Pr1 O5 159.38(11) 3_566 3_667 ?
O1 Pr1 C4 69.17(14) . 3_566 ?
O6 Pr1 C4 143.76(13) 3_667 3_566 ?
O4 Pr1 C4 92.00(13) 2_556 3_566 ?
O7 Pr1 C4 94.92(14) . 3_566 ?
O5 Pr1 C4 94.59(13) 2_656 3_566 ?
O2 Pr1 C4 97.95(14) 4_576 3_566 ?
O3 Pr1 C4 24.96(13) 3_566 3_566 ?
O4 Pr1 C4 25.61(12) 3_566 3_566 ?
O5 Pr1 C4 162.00(13) 3_667 3_566 ?
O1 Pr1 C12 98.96(14) . 3_667 ?
O6 Pr1 C12 24.68(12) 3_667 3_667 ?
O4 Pr1 C12 93.11(13) 2_556 3_667 ?
O7 Pr1 C12 74.17(14) . 3_667 ?
O5 Pr1 C12 88.77(13) 2_656 3_667 ?
O2 Pr1 C12 96.11(14) 4_576 3_667 ?
O3 Pr1 C12 146.28(14) 3_566 3_667 ?
O4 Pr1 C12 160.28(12) 3_566 3_667 ?
O5 Pr1 C12 25.41(12) 3_667 3_667 ?
C4 Pr1 C12 165.91(14) 3_566 3_667 ?
C1 O1 Pr1 144.6(4) . . ?
C1 O2 Pr1 132.5(3) . 4_575 ?
C4 O3 Pr1 94.9(3) . 3_566 ?
C4 O4 Pr1 137.5(3) . 2_546 ?
C4 O4 Pr1 93.3(3) . 3_566 ?
Pr1 O4 Pr1 111.06(13) 2_546 3_566 ?
C12 O5 Pr1 156.5(3) . 2_646 ?
C12 O5 Pr1 88.3(3) . 3_667 ?
Pr1 O5 Pr1 106.23(12) 2_646 3_667 ?
C12 O6 Pr1 100.7(3) . 3_667 ?
Pr1 O7 H7A 106.7 . . ?
Pr1 O7 H7B 145.0 . . ?
H7A O7 H7B 107.8 . . ?
O1 C1 O2 127.4(5) . . ?
O1 C1 C2 114.9(4) . . ?
O2 C1 C2 117.7(4) . . ?
N1 C2 C3 108.7(4) . . ?
N1 C2 C1 107.0(4) . . ?
C3 C2 C1 113.2(4) . . ?
N1 C2 H2 109.3 . . ?
C3 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
C4 C3 C2 112.8(4) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
O3 C4 O4 120.1(5) . . ?
O3 C4 C3 121.4(5) . . ?
O4 C4 C3 118.5(5) . . ?
O3 C4 Pr1 60.1(3) . 3_566 ?
O4 C4 Pr1 61.1(3) . 3_566 ?
C3 C4 Pr1 168.8(4) . 3_566 ?
N1 C5 C6 112.3(4) . . ?
N1 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N1 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C11 119.7(5) . . ?
C7 C6 C5 119.6(5) . . ?
C11 C6 C5 120.7(5) . . ?
C6 C7 C8 120.5(5) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 119.8(5) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 120.1(5) . . ?
C10 C9 C12 121.3(5) . . ?
C8 C9 C12 118.5(5) . . ?
C9 C10 C11 119.9(5) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C6 C11 C10 119.9(5) . . ?
C6 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
O6 C12 O5 120.9(5) . . ?
O6 C12 C9 118.1(4) . . ?
O5 C12 C9 121.0(5) . . ?
O6 C12 Pr1 54.6(3) . 3_667 ?
O5 C12 Pr1 66.3(3) . 3_667 ?
C9 C12 Pr1 171.9(4) . 3_667 ?
C5 N1 C2 112.2(4) . . ?
C5 N1 H1A 109.2 . . ?
C2 N1 H1A 109.2 . . ?
C5 N1 H1B 109.2 . . ?
C2 N1 H1B 109.2 . . ?
H1A N1 H1B 107.9 . . ?

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
Pr1 O1 C1 O2 8.1(11) . . . . ?
Pr1 O1 C1 C2 -171.3(4) . . . . ?
Pr1 O2 C1 O1 13.5(9) 4_575 . . . ?
Pr1 O2 C1 C2 -167.1(3) 4_575 . . . ?
O1 C1 C2 N1 -51.7(6) . . . . ?
O2 C1 C2 N1 128.9(5) . . . . ?
O1 C1 C2 C3 68.1(6) . . . . ?
O2 C1 C2 C3 -111.4(5) . . . . ?
N1 C2 C3 C4 -144.2(4) . . . . ?
C1 C2 C3 C4 97.0(5) . . . . ?
Pr1 O3 C4 O4 11.9(5) 3_566 . . . ?
Pr1 O3 C4 C3 -167.0(4) 3_566 . . . ?
Pr1 O4 C4 O3 -138.4(5) 2_546 . . . ?
Pr1 O4 C4 O3 -11.8(5) 3_566 . . . ?
Pr1 O4 C4 C3 40.6(7) 2_546 . . . ?
Pr1 O4 C4 C3 167.2(4) 3_566 . . . ?
Pr1 O4 C4 Pr1 -126.6(4) 2_546 . . 3_566 ?
C2 C3 C4 O3 -9.1(7) . . . . ?
C2 C3 C4 O4 171.9(4) . . . . ?
C2 C3 C4 Pr1 -103.4(18) . . . 3_566 ?
N1 C5 C6 C7 -97.8(6) . . . . ?
N1 C5 C6 C11 83.9(7) . . . . ?
C11 C6 C7 C8 1.6(9) . . . . ?
C5 C6 C7 C8 -176.8(5) . . . . ?
C6 C7 C8 C9 0.7(9) . . . . ?
C7 C8 C9 C10 -2.3(8) . . . . ?
C7 C8 C9 C12 -179.3(5) . . . . ?
C8 C9 C10 C11 1.7(8) . . . . ?
C12 C9 C10 C11 178.5(5) . . . . ?
C7 C6 C11 C10 -2.2(8) . . . . ?
C5 C6 C11 C10 176.1(5) . . . . ?
C9 C10 C11 C6 0.6(9) . . . . ?
Pr1 O6 C12 O5 -1.6(5) 3_667 . . . ?
Pr1 O6 C12 C9 175.9(4) 3_667 . . . ?
Pr1 O5 C12 O6 -127.8(7) 2_646 . . . ?
Pr1 O5 C12 O6 1.4(5) 3_667 . . . ?
Pr1 O5 C12 C9 54.7(11) 2_646 . . . ?
Pr1 O5 C12 C9 -176.1(4) 3_667 . . . ?
Pr1 O5 C12 Pr1 -129.2(8) 2_646 . . 3_667 ?
C10 C9 C12 O6 -154.8(5) . . . . ?
C8 C9 C12 O6 22.1(7) . . . . ?
C10 C9 C12 O5 22.7(8) . . . . ?
C8 C9 C12 O5 -160.4(5) . . . . ?
C6 C5 N1 C2 177.8(5) . . . . ?
C3 C2 N1 C5 170.3(4) . . . . ?
C1 C2 N1 C5 -67.2(5) . . . . ?

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 H7B O3 0.83 2.36 3.089(5) 148.0 1_556
O7 H7B O2 0.83 2.57 3.078(6) 121.5 1_556
O7 H7A Cl1 0.82 2.55 3.175(4) 133.3 4_566
N1 H1B Cl1 0.89 2.20 3.060(4) 163.3 .
N1 H1A Cl1 0.89 2.43 3.242(5) 152.7 4_566

_refine_diff_density_max         1.460
_refine_diff_density_min         -0.939
_refine_diff_density_rms         0.142



####################################################################### 
# 
# 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_ZYT_15
_database_code_depnum_ccdc_archive 'CCDC 2236707'
loop_
_audit_author_name
_audit_author_address
'Yatong Zhang'
;Shanxi University Institute of Molecular Science
China
;
_audit_update_record             
;
2023-01-17 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H13 Eu N O7, Cl'
_chemical_formula_sum            'C12 H13 Cl Eu N O7'
_chemical_formula_weight         470.64

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.1578 3.6682 '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                   14.365(4)
_cell_length_b                   12.400(4)
_cell_length_c                   7.874(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.572(8)
_cell_angle_gamma                90
_cell_volume                     1395.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4531
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      28.24

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.240
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    4.720
_shelx_estimated_absorpt_T_min   0.332
_shelx_estimated_absorpt_T_max   0.538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4889
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microsource'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11096
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.075
_diffrn_reflns_theta_max         28.272
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             3402
_reflns_number_gt                2588
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0278P)²+8.7385P] 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         3402
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
Eu1 Eu 0.13896(2) 0.70141(3) 0.86672(4) 0.02497(11) Uani 1 1 d . . . . .
O1 O 0.1613(4) 0.5606(4) 0.6700(7) 0.0424(13) Uani 1 1 d . . . . .
O2 O 0.1419(4) 0.6003(4) 0.3935(7) 0.0445(14) Uani 1 1 d . . . . .
O3 O 0.0210(4) 0.3635(6) 0.2442(8) 0.0549(17) Uani 1 1 d . . . . .
O4 O -0.0420(3) 0.2483(4) 0.4100(7) 0.0332(11) Uani 1 1 d . . . . .
O5 O 0.7562(3) 0.2726(4) 0.8359(8) 0.0393(13) Uani 1 1 d . . . . .
O6 O 0.7134(4) 0.3777(5) 1.0362(7) 0.0439(13) Uani 1 1 d . . . . .
O7 O 0.1052(4) 0.5365(4) 1.0187(7) 0.0420(13) Uani 1 1 d . . . . .
H7A H 0.1208 0.4864 0.9599 0.063 Uiso 1 1 d R U . . .
H7B H 0.0905 0.5110 1.1082 0.063 Uiso 1 1 d R U . . .
C1 C 0.1555(5) 0.5370(6) 0.5166(9) 0.0292(14) Uani 1 1 d . . . . .
C2 C 0.1709(5) 0.4174(5) 0.4777(10) 0.0300(15) Uani 1 1 d . . . . .
H2 H 0.1766 0.4082 0.3556 0.036 Uiso 1 1 calc R U . . .
C3 C 0.0939(5) 0.3434(6) 0.5318(10) 0.0351(16) Uani 1 1 d . . . . .
H3A H 0.1219 0.2769 0.5767 0.042 Uiso 1 1 calc R U . . .
H3B H 0.0639 0.3780 0.6227 0.042 Uiso 1 1 calc R U . . .
C4 C 0.0203(5) 0.3170(6) 0.3863(10) 0.0344(16) Uani 1 1 d . . . . .
C5 C 0.3440(5) 0.4365(7) 0.5155(11) 0.0417(19) Uani 1 1 d . . . . .
H5A H 0.3466 0.4178 0.3964 0.050 Uiso 1 1 calc R U . . .
H5B H 0.3367 0.5141 0.5221 0.050 Uiso 1 1 calc R U . . .
C6 C 0.4329(5) 0.4057(6) 0.6119(10) 0.0330(15) Uani 1 1 d . . . . .
C7 C 0.4721(5) 0.4735(7) 0.7404(11) 0.0413(18) Uani 1 1 d . . . . .
H7 H 0.4399 0.5353 0.7673 0.050 Uiso 1 1 calc R U . . .
C8 C 0.5578(5) 0.4513(6) 0.8291(10) 0.0369(17) Uani 1 1 d . . . . .
H8 H 0.5832 0.4980 0.9138 0.044 Uiso 1 1 calc R U . . .
C9 C 0.6057(5) 0.3586(6) 0.7902(9) 0.0288(14) Uani 1 1 d . . . . .
C10 C 0.5661(5) 0.2898(6) 0.6685(11) 0.0378(17) Uani 1 1 d . . . . .
H10 H 0.5975 0.2270 0.6438 0.045 Uiso 1 1 calc R U . . .
C11 C 0.4792(5) 0.3124(7) 0.5806(11) 0.0410(18) Uani 1 1 d . . . . .
H11 H 0.4526 0.2637 0.5001 0.049 Uiso 1 1 calc R U . . .
C12 C 0.6978(5) 0.3350(6) 0.8920(10) 0.0319(15) Uani 1 1 d . . . . .
N1 N 0.2603(4) 0.3836(4) 0.5781(8) 0.0304(13) Uani 1 1 d . . . . .
H1A H 0.2576 0.4004 0.6874 0.036 Uiso 1 1 calc R U . . .
H1B H 0.2663 0.3123 0.5711 0.036 Uiso 1 1 calc R U . . .
Cl1 Cl 0.26050(17) 0.14342(16) 0.4868(3) 0.0525(6) 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
Eu1 O1 2.376(5) . ?
Eu1 O6 2.394(5) 3_667 ?
Eu1 O4 2.417(5) 2_556 ?
Eu1 O7 2.441(5) . ?
Eu1 O5 2.461(6) 2_656 ?
Eu1 O2 2.468(6) 4_576 ?
Eu1 O3 2.510(6) 3_566 ?
Eu1 O4 2.546(5) 3_566 ?
Eu1 O5 2.678(6) 3_667 ?
Eu1 C4 2.893(8) 3_566 ?
Eu1 C12 2.906(8) 3_667 ?
Eu1 Eu1 4.1173(12) 4_575 ?
Eu1 H7A 2.7836 . ?
O1 C1 1.238(9) . ?
O2 C1 1.248(9) . ?
O2 Eu1 2.468(6) 4_575 ?
O3 C4 1.259(10) . ?
O3 Eu1 2.510(6) 3_566 ?
O4 C4 1.263(8) . ?
O4 Eu1 2.417(5) 2_546 ?
O4 Eu1 2.546(5) 3_566 ?
O5 C12 1.253(9) . ?
O5 Eu1 2.461(6) 2_646 ?
O5 Eu1 2.678(6) 3_667 ?
O6 C12 1.254(9) . ?
O6 Eu1 2.394(5) 3_667 ?
O7 H7A 0.8191 . ?
O7 H7B 0.8185 . ?
C1 C2 1.534(9) . ?
C2 N1 1.501(8) . ?
C2 C3 1.529(10) . ?
C2 H2 0.9800 . ?
C3 C4 1.517(10) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 Eu1 2.893(8) 3_566 ?
C5 C6 1.472(9) . ?
C5 N1 1.495(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C11 1.369(10) . ?
C6 C7 1.392(11) . ?
C7 C8 1.383(11) . ?
C7 H7 0.9300 . ?
C8 C9 1.389(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.365(10) . ?
C9 C12 1.508(10) . ?
C10 C11 1.396(11) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 Eu1 2.906(8) 3_667 ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?

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 Eu1 O6 74.7(2) . 3_667 ?
O1 Eu1 O4 140.76(19) . 2_556 ?
O6 Eu1 O4 114.91(18) 3_667 2_556 ?
O1 Eu1 O7 75.5(2) . . ?
O6 Eu1 O7 73.25(19) 3_667 . ?
O4 Eu1 O7 71.88(18) 2_556 . ?
O1 Eu1 O5 73.21(19) . 2_656 ?
O6 Eu1 O5 77.01(19) 3_667 2_656 ?
O4 Eu1 O5 144.79(18) 2_556 2_656 ?
O7 Eu1 O5 141.36(19) . 2_656 ?
O1 Eu1 O2 141.76(19) . 4_576 ?
O6 Eu1 O2 111.9(2) 3_667 4_576 ?
O4 Eu1 O2 72.82(17) 2_556 4_576 ?
O7 Eu1 O2 142.67(18) . 4_576 ?
O5 Eu1 O2 72.03(18) 2_656 4_576 ?
O1 Eu1 O3 73.4(2) . 3_566 ?
O6 Eu1 O3 137.1(2) 3_667 3_566 ?
O4 Eu1 O3 76.0(2) 2_556 3_566 ?
O7 Eu1 O3 71.6(2) . 3_566 ?
O5 Eu1 O3 119.09(19) 2_656 3_566 ?
O2 Eu1 O3 110.9(2) 4_576 3_566 ?
O1 Eu1 O4 73.70(18) . 3_566 ?
O6 Eu1 O4 140.12(18) 3_667 3_566 ?
O4 Eu1 O4 104.94(16) 2_556 3_566 ?
O7 Eu1 O4 120.44(18) . 3_566 ?
O5 Eu1 O4 71.07(17) 2_656 3_566 ?
O2 Eu1 O4 80.36(18) 4_576 3_566 ?
O3 Eu1 O4 51.30(18) 3_566 3_566 ?
O1 Eu1 O5 123.96(17) . 3_667 ?
O6 Eu1 O5 50.55(18) 3_667 3_667 ?
O4 Eu1 O5 69.48(16) 2_556 3_667 ?
O7 Eu1 O5 78.09(18) . 3_667 ?
O5 Eu1 O5 101.32(16) 2_656 3_667 ?
O2 Eu1 O5 78.56(18) 4_576 3_667 ?
O3 Eu1 O5 139.55(19) 3_566 3_667 ?
O4 Eu1 O5 158.90(17) 3_566 3_667 ?
O1 Eu1 C4 68.9(2) . 3_566 ?
O6 Eu1 C4 143.5(2) 3_667 3_566 ?
O4 Eu1 C4 92.71(19) 2_556 3_566 ?
O7 Eu1 C4 95.2(2) . 3_566 ?
O5 Eu1 C4 94.27(19) 2_656 3_566 ?
O2 Eu1 C4 98.3(2) 4_576 3_566 ?
O3 Eu1 C4 25.72(19) 3_566 3_566 ?
O4 Eu1 C4 25.85(18) 3_566 3_566 ?
O5 Eu1 C4 162.12(19) 3_667 3_566 ?
O1 Eu1 C12 99.3(2) . 3_667 ?
O6 Eu1 C12 25.1(2) 3_667 3_667 ?
O4 Eu1 C12 92.68(19) 2_556 3_667 ?
O7 Eu1 C12 74.64(19) . 3_667 ?
O5 Eu1 C12 88.52(19) 2_656 3_667 ?
O2 Eu1 C12 95.3(2) 4_576 3_667 ?
O3 Eu1 C12 146.2(2) 3_566 3_667 ?
O4 Eu1 C12 159.52(18) 3_566 3_667 ?
O5 Eu1 C12 25.51(18) 3_667 3_667 ?
C4 Eu1 C12 166.4(2) 3_566 3_667 ?
O1 Eu1 Eu1 65.11(13) . 4_575 ?
O6 Eu1 Eu1 110.07(14) 3_667 4_575 ?
O4 Eu1 Eu1 132.74(12) 2_556 4_575 ?
O7 Eu1 Eu1 137.09(13) . 4_575 ?
O5 Eu1 Eu1 38.59(13) 2_656 4_575 ?
O2 Eu1 Eu1 77.79(13) 4_576 4_575 ?
O3 Eu1 Eu1 81.14(14) 3_566 4_575 ?
O4 Eu1 Eu1 32.97(11) 3_566 4_575 ?
O5 Eu1 Eu1 138.49(12) 3_667 4_575 ?
C4 Eu1 Eu1 55.80(15) 3_566 4_575 ?
C12 Eu1 Eu1 126.57(14) 3_667 4_575 ?
O1 Eu1 H7A 59.4 . . ?
O6 Eu1 H7A 68.0 3_667 . ?
O4 Eu1 H7A 87.9 2_556 . ?
O7 Eu1 H7A 16.4 . . ?
O5 Eu1 H7A 126.4 2_656 . ?
O2 Eu1 H7A 158.9 4_576 . ?
O3 Eu1 H7A 71.3 3_566 . ?
O4 Eu1 H7A 113.7 3_566 . ?
O5 Eu1 H7A 86.8 3_667 . ?
C4 Eu1 H7A 91.0 3_566 . ?
C12 Eu1 H7A 76.7 3_667 . ?
Eu1 Eu1 H7A 122.8 4_575 . ?
C1 O1 Eu1 144.0(5) . . ?
C1 O2 Eu1 133.9(5) . 4_575 ?
C4 O3 Eu1 94.4(4) . 3_566 ?
C4 O4 Eu1 137.4(5) . 2_546 ?
C4 O4 Eu1 92.6(4) . 3_566 ?
Eu1 O4 Eu1 112.06(18) 2_546 3_566 ?
C12 O5 Eu1 157.3(5) . 2_646 ?
C12 O5 Eu1 87.5(5) . 3_667 ?
Eu1 O5 Eu1 106.42(18) 2_646 3_667 ?
C12 O6 Eu1 101.0(5) . 3_667 ?
Eu1 O7 H7A 106.3 . . ?
Eu1 O7 H7B 145.7 . . ?
H7A O7 H7B 107.5 . . ?
O1 C1 O2 126.8(7) . . ?
O1 C1 C2 115.2(6) . . ?
O2 C1 C2 117.9(6) . . ?
N1 C2 C3 106.9(6) . . ?
N1 C2 C1 107.3(5) . . ?
C3 C2 C1 113.7(6) . . ?
N1 C2 H2 109.6 . . ?
C3 C2 H2 109.6 . . ?
C1 C2 H2 109.6 . . ?
C4 C3 C2 112.9(6) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
O3 C4 O4 120.5(7) . . ?
O3 C4 C3 120.5(7) . . ?
O4 C4 C3 119.1(7) . . ?
O3 C4 Eu1 59.9(4) . 3_566 ?
O4 C4 Eu1 61.6(4) . 3_566 ?
C3 C4 Eu1 169.6(5) . 3_566 ?
C6 C5 N1 113.7(6) . . ?
C6 C5 H5A 108.8 . . ?
N1 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
N1 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C11 C6 C7 118.2(7) . . ?
C11 C6 C5 122.6(8) . . ?
C7 C6 C5 119.2(7) . . ?
C8 C7 C6 121.6(7) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 119.3(7) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 119.4(6) . . ?
C10 C9 C12 122.4(6) . . ?
C8 C9 C12 118.1(7) . . ?
C9 C10 C11 121.0(7) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C6 C11 C10 120.4(7) . . ?
C6 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
O5 C12 O6 120.9(7) . . ?
O5 C12 C9 121.1(7) . . ?
O6 C12 C9 118.0(6) . . ?
O5 C12 Eu1 67.0(4) . 3_667 ?
O6 C12 Eu1 54.0(4) . 3_667 ?
C9 C12 Eu1 171.2(5) . 3_667 ?
C5 N1 C2 112.2(6) . . ?
C5 N1 H1A 109.2 . . ?
C2 N1 H1A 109.2 . . ?
C5 N1 H1B 109.2 . . ?
C2 N1 H1B 109.2 . . ?
H1A N1 H1B 107.9 . . ?

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
Eu1 O1 C1 O2 10.5(14) . . . . ?
Eu1 O1 C1 C2 -172.2(6) . . . . ?
Eu1 O2 C1 O1 9.2(12) 4_575 . . . ?
Eu1 O2 C1 C2 -168.1(4) 4_575 . . . ?
O1 C1 C2 N1 -50.7(8) . . . . ?
O2 C1 C2 N1 126.9(7) . . . . ?
O1 C1 C2 C3 67.3(8) . . . . ?
O2 C1 C2 C3 -115.1(7) . . . . ?
N1 C2 C3 C4 -145.0(6) . . . . ?
C1 C2 C3 C4 96.8(8) . . . . ?
Eu1 O3 C4 O4 11.7(8) 3_566 . . . ?
Eu1 O3 C4 C3 -167.9(6) 3_566 . . . ?
Eu1 O4 C4 O3 -138.7(7) 2_546 . . . ?
Eu1 O4 C4 O3 -11.5(8) 3_566 . . . ?
Eu1 O4 C4 C3 40.9(10) 2_546 . . . ?
Eu1 O4 C4 C3 168.1(6) 3_566 . . . ?
Eu1 O4 C4 Eu1 -127.2(6) 2_546 . . 3_566 ?
C2 C3 C4 O3 -7.3(10) . . . . ?
C2 C3 C4 O4 173.1(6) . . . . ?
C2 C3 C4 Eu1 -96(3) . . . 3_566 ?
N1 C5 C6 C11 82.0(10) . . . . ?
N1 C5 C6 C7 -98.0(9) . . . . ?
C11 C6 C7 C8 3.3(12) . . . . ?
C5 C6 C7 C8 -176.6(8) . . . . ?
C6 C7 C8 C9 -0.6(13) . . . . ?
C7 C8 C9 C10 -1.7(12) . . . . ?
C7 C8 C9 C12 -178.5(7) . . . . ?
C8 C9 C10 C11 1.2(12) . . . . ?
C12 C9 C10 C11 177.9(7) . . . . ?
C7 C6 C11 C10 -3.8(12) . . . . ?
C5 C6 C11 C10 176.2(8) . . . . ?
C9 C10 C11 C6 1.6(13) . . . . ?
Eu1 O5 C12 O6 -126.8(11) 2_646 . . . ?
Eu1 O5 C12 O6 2.2(7) 3_667 . . . ?
Eu1 O5 C12 C9 54.9(16) 2_646 . . . ?
Eu1 O5 C12 C9 -176.2(6) 3_667 . . . ?
Eu1 O5 C12 Eu1 -129.0(13) 2_646 . . 3_667 ?
Eu1 O6 C12 O5 -2.5(8) 3_667 . . . ?
Eu1 O6 C12 C9 175.9(5) 3_667 . . . ?
C10 C9 C12 O5 23.6(11) . . . . ?
C8 C9 C12 O5 -159.7(7) . . . . ?
C10 C9 C12 O6 -154.7(8) . . . . ?
C8 C9 C12 O6 21.9(10) . . . . ?
C6 C5 N1 C2 179.6(7) . . . . ?
C3 C2 N1 C5 169.9(6) . . . . ?
C1 C2 N1 C5 -67.8(8) . . . . ?

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 H7B O3 0.82 2.39 3.105(8) 146.8 1_556
O7 H7B O2 0.82 2.55 3.051(8) 120.9 1_556
O7 H7A Cl1 0.82 2.57 3.182(6) 133.2 4_566
N1 H1B Cl1 0.89 2.20 3.064(6) 164.7 .
N1 H1A Cl1 0.89 2.42 3.235(7) 153.2 4_566

_refine_diff_density_max         1.878
_refine_diff_density_min         -1.410
_refine_diff_density_rms         0.186



####################################################################### 
# 
# 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_ZYT_18
_database_code_depnum_ccdc_archive 'CCDC 2236706'
loop_
_audit_author_name
_audit_author_address
'Yatong Zhang'
;Shanxi University Institute of Molecular Science
China
;
_audit_update_record             
;
2023-01-17 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H13 N O7 Sm, Cl'
_chemical_formula_sum            'C12 H13 Cl N O7 Sm'
_chemical_formula_weight         469.03

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sm Sm -0.1638 3.4418 '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                   14.3665(16)
_cell_length_b                   12.3921(13)
_cell_length_c                   7.8827(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.556(3)
_cell_angle_gamma                90
_cell_volume                     1396.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8269
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      28.26

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.230
_exptl_crystal_F_000             908
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    4.431
_shelx_estimated_absorpt_T_min   0.350
_shelx_estimated_absorpt_T_max   0.556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5518
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microsource'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13297
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.849
_diffrn_reflns_theta_max         28.286
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3441
_reflns_number_gt                3030
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0187P)²+4.6031P] 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         3441
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0684
_refine_ls_wR_factor_gt          0.0659
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_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
Sm1 Sm 0.13909(2) 0.70133(2) 0.86604(2) 0.02174(7) Uani 1 1 d . . . . .
O1 O 0.1619(2) 0.5600(2) 0.6685(4) 0.0397(7) Uani 1 1 d . . . . .
O2 O 0.1413(2) 0.5992(2) 0.3915(4) 0.0409(8) Uani 1 1 d . . . . .
O3 O 0.0213(2) 0.3633(3) 0.2446(4) 0.0499(9) Uani 1 1 d . . . . .
O4 O -0.04180(19) 0.2487(2) 0.4090(4) 0.0301(6) Uani 1 1 d . . . . .
O5 O 0.7559(2) 0.2720(3) 0.8377(4) 0.0366(7) Uani 1 1 d . . . . .
O6 O 0.7125(2) 0.3781(3) 1.0366(4) 0.0372(7) Uani 1 1 d . . . . .
O7 O 0.1060(2) 0.5357(2) 1.0185(4) 0.0401(7) Uani 1 1 d . . . . .
H7A H 0.1216 0.4856 0.9597 0.060 Uiso 1 1 d R U . . .
H7B H 0.0913 0.5102 1.1080 0.060 Uiso 1 1 d R U . . .
C1 C 0.1564(3) 0.5369(3) 0.5157(5) 0.0265(8) Uani 1 1 d . . . . .
C2 C 0.1714(3) 0.4167(3) 0.4771(5) 0.0280(8) Uani 1 1 d . . . . .
H2 H 0.1773 0.4073 0.3552 0.034 Uiso 1 1 calc R U . . .
C3 C 0.0931(3) 0.3445(3) 0.5304(5) 0.0310(8) Uani 1 1 d . . . . .
H3A H 0.1202 0.2781 0.5780 0.037 Uiso 1 1 calc R U . . .
H3B H 0.0625 0.3806 0.6190 0.037 Uiso 1 1 calc R U . . .
C4 C 0.0213(3) 0.3173(3) 0.3860(5) 0.0289(8) Uani 1 1 d . . . . .
C5 C 0.3434(3) 0.4355(4) 0.5135(6) 0.0392(10) Uani 1 1 d . . . . .
H5A H 0.3356 0.5132 0.5167 0.047 Uiso 1 1 calc R U . . .
H5B H 0.3466 0.4147 0.3956 0.047 Uiso 1 1 calc R U . . .
C6 C 0.4337(3) 0.4058(4) 0.6148(5) 0.0313(9) Uani 1 1 d . . . . .
C7 C 0.4724(3) 0.4747(4) 0.7396(6) 0.0382(10) Uani 1 1 d . . . . .
H7 H 0.4408 0.5374 0.7643 0.046 Uiso 1 1 calc R U . . .
C8 C 0.5577(3) 0.4514(4) 0.8285(6) 0.0353(9) Uani 1 1 d . . . . .
H8 H 0.5830 0.4979 0.9133 0.042 Uiso 1 1 calc R U . . .
C9 C 0.6053(3) 0.3586(3) 0.7910(5) 0.0271(8) Uani 1 1 d . . . . .
C10 C 0.5663(3) 0.2888(3) 0.6688(6) 0.0346(9) Uani 1 1 d . . . . .
H10 H 0.5976 0.2258 0.6447 0.042 Uiso 1 1 calc R U . . .
C11 C 0.4799(3) 0.3122(4) 0.5810(6) 0.0372(10) Uani 1 1 d . . . . .
H11 H 0.4533 0.2643 0.4993 0.045 Uiso 1 1 calc R U . . .
C12 C 0.6971(3) 0.3353(3) 0.8928(6) 0.0292(8) Uani 1 1 d . . . . .
N1 N 0.2607(2) 0.3832(3) 0.5780(4) 0.0264(7) Uani 1 1 d . . . . .
H1A H 0.2582 0.4009 0.6869 0.032 Uiso 1 1 calc R U . . .
H1B H 0.2668 0.3118 0.5722 0.032 Uiso 1 1 calc R U . . .
Cl1 Cl 0.26110(10) 0.14364(9) 0.48514(19) 0.0513(3) 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
Sm1 O1 2.387(3) . ?
Sm1 O6 2.405(3) 3_667 ?
Sm1 O4 2.433(3) 2_556 ?
Sm1 O7 2.449(3) . ?
Sm1 O5 2.468(3) 2_656 ?
Sm1 O2 2.480(3) 4_576 ?
Sm1 O3 2.515(3) 3_566 ?
Sm1 O4 2.540(3) 3_566 ?
Sm1 O5 2.675(3) 3_667 ?
Sm1 C4 2.903(4) 3_566 ?
Sm1 C12 2.914(4) 3_667 ?
O1 C1 1.233(5) . ?
O2 C1 1.248(5) . ?
O2 Sm1 2.480(3) 4_575 ?
O3 C4 1.252(5) . ?
O3 Sm1 2.515(3) 3_566 ?
O4 C4 1.269(5) . ?
O4 Sm1 2.433(3) 2_546 ?
O4 Sm1 2.540(3) 3_566 ?
O5 C12 1.260(5) . ?
O5 Sm1 2.468(3) 2_646 ?
O5 Sm1 2.675(3) 3_667 ?
O6 C12 1.252(5) . ?
O6 Sm1 2.405(3) 3_667 ?
O7 H7A 0.8191 . ?
O7 H7B 0.8191 . ?
C1 C2 1.540(5) . ?
C2 N1 1.501(5) . ?
C2 C3 1.528(5) . ?
C2 H2 0.9800 . ?
C3 C4 1.499(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 Sm1 2.903(4) 3_566 ?
C5 N1 1.486(5) . ?
C5 C6 1.502(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C11 1.376(6) . ?
C6 C7 1.378(6) . ?
C7 C8 1.382(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.384(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.374(6) . ?
C9 C12 1.504(6) . ?
C10 C11 1.392(6) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 Sm1 2.914(4) 3_667 ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?

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 Sm1 O6 74.62(11) . 3_667 ?
O1 Sm1 O4 140.98(11) . 2_556 ?
O6 Sm1 O4 114.83(10) 3_667 2_556 ?
O1 Sm1 O7 75.56(11) . . ?
O6 Sm1 O7 73.03(11) 3_667 . ?
O4 Sm1 O7 72.06(10) 2_556 . ?
O1 Sm1 O5 72.82(11) . 2_656 ?
O6 Sm1 O5 76.96(11) 3_667 2_656 ?
O4 Sm1 O5 145.00(11) 2_556 2_656 ?
O7 Sm1 O5 140.96(11) . 2_656 ?
O1 Sm1 O2 141.50(11) . 4_576 ?
O6 Sm1 O2 112.22(11) 3_667 4_576 ?
O4 Sm1 O2 72.81(10) 2_556 4_576 ?
O7 Sm1 O2 142.89(11) . 4_576 ?
O5 Sm1 O2 72.26(11) 2_656 4_576 ?
O1 Sm1 O3 73.68(13) . 3_566 ?
O6 Sm1 O3 137.26(13) 3_667 3_566 ?
O4 Sm1 O3 75.98(11) 2_556 3_566 ?
O7 Sm1 O3 71.85(11) . 3_566 ?
O5 Sm1 O3 118.98(11) 2_656 3_566 ?
O2 Sm1 O3 110.46(12) 4_576 3_566 ?
O1 Sm1 O4 73.80(10) . 3_566 ?
O6 Sm1 O4 140.33(10) 3_667 3_566 ?
O4 Sm1 O4 104.82(9) 2_556 3_566 ?
O7 Sm1 O4 120.45(10) . 3_566 ?
O5 Sm1 O4 71.25(10) 2_656 3_566 ?
O2 Sm1 O4 80.07(10) 4_576 3_566 ?
O3 Sm1 O4 51.06(10) 3_566 3_566 ?
O1 Sm1 O5 123.98(10) . 3_667 ?
O6 Sm1 O5 50.55(10) 3_667 3_667 ?
O4 Sm1 O5 69.47(9) 2_556 3_667 ?
O7 Sm1 O5 78.17(10) . 3_667 ?
O5 Sm1 O5 101.28(10) 2_656 3_667 ?
O2 Sm1 O5 78.71(10) 4_576 3_667 ?
O3 Sm1 O5 139.70(10) 3_566 3_667 ?
O4 Sm1 O5 158.77(10) 3_566 3_667 ?
O1 Sm1 C4 69.22(11) . 3_566 ?
O6 Sm1 C4 143.75(11) 3_667 3_566 ?
O4 Sm1 C4 92.50(10) 2_556 3_566 ?
O7 Sm1 C4 95.19(11) . 3_566 ?
O5 Sm1 C4 94.46(11) 2_656 3_566 ?
O2 Sm1 C4 97.91(11) 4_576 3_566 ?
O3 Sm1 C4 25.44(11) 3_566 3_566 ?
O4 Sm1 C4 25.88(10) 3_566 3_566 ?
O5 Sm1 C4 161.91(10) 3_667 3_566 ?
O1 Sm1 C12 99.12(12) . 3_667 ?
O6 Sm1 C12 24.95(11) 3_667 3_667 ?
O4 Sm1 C12 92.67(11) 2_556 3_667 ?
O7 Sm1 C12 74.45(11) . 3_667 ?
O5 Sm1 C12 88.50(11) 2_656 3_667 ?
O2 Sm1 C12 95.68(11) 4_576 3_667 ?
O3 Sm1 C12 146.29(11) 3_566 3_667 ?
O4 Sm1 C12 159.68(10) 3_566 3_667 ?
O5 Sm1 C12 25.60(10) 3_667 3_667 ?
C4 Sm1 C12 166.35(12) 3_566 3_667 ?
C1 O1 Sm1 143.9(3) . . ?
C1 O2 Sm1 132.8(3) . 4_575 ?
C4 O3 Sm1 94.9(3) . 3_566 ?
C4 O4 Sm1 137.3(3) . 2_546 ?
C4 O4 Sm1 93.2(2) . 3_566 ?
Sm1 O4 Sm1 111.92(10) 2_546 3_566 ?
C12 O5 Sm1 156.5(3) . 2_646 ?
C12 O5 Sm1 87.8(3) . 3_667 ?
Sm1 O5 Sm1 106.46(10) 2_646 3_667 ?
C12 O6 Sm1 100.9(3) . 3_667 ?
Sm1 O7 H7A 106.3 . . ?
Sm1 O7 H7B 145.6 . . ?
H7A O7 H7B 107.6 . . ?
O1 C1 O2 127.8(4) . . ?
O1 C1 C2 114.8(4) . . ?
O2 C1 C2 117.4(4) . . ?
N1 C2 C3 107.8(3) . . ?
N1 C2 C1 107.0(3) . . ?
C3 C2 C1 113.1(3) . . ?
N1 C2 H2 109.6 . . ?
C3 C2 H2 109.6 . . ?
C1 C2 H2 109.6 . . ?
C4 C3 C2 113.2(3) . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.8 . . ?
O3 C4 O4 119.6(4) . . ?
O3 C4 C3 120.9(4) . . ?
O4 C4 C3 119.4(4) . . ?
O3 C4 Sm1 59.7(2) . 3_566 ?
O4 C4 Sm1 60.9(2) . 3_566 ?
C3 C4 Sm1 168.6(3) . 3_566 ?
N1 C5 C6 112.9(4) . . ?
N1 C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
N1 C5 H5B 109.0 . . ?
C6 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C11 C6 C7 119.5(4) . . ?
C11 C6 C5 120.8(4) . . ?
C7 C6 C5 119.7(4) . . ?
C6 C7 C8 120.6(4) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 119.9(4) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 119.7(4) . . ?
C10 C9 C12 122.0(4) . . ?
C8 C9 C12 118.2(4) . . ?
C9 C10 C11 120.1(4) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C6 C11 C10 120.2(4) . . ?
C6 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
O6 C12 O5 120.7(4) . . ?
O6 C12 C9 118.1(4) . . ?
O5 C12 C9 121.2(4) . . ?
O6 C12 Sm1 54.1(2) . 3_667 ?
O5 C12 Sm1 66.6(2) . 3_667 ?
C9 C12 Sm1 171.5(3) . 3_667 ?
C5 N1 C2 111.6(3) . . ?
C5 N1 H1A 109.3 . . ?
C2 N1 H1A 109.3 . . ?
C5 N1 H1B 109.3 . . ?
C2 N1 H1B 109.3 . . ?
H1A N1 H1B 108.0 . . ?

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
Sm1 O1 C1 O2 8.8(8) . . . . ?
Sm1 O1 C1 C2 -172.0(3) . . . . ?
Sm1 O2 C1 O1 11.5(7) 4_575 . . . ?
Sm1 O2 C1 C2 -167.7(3) 4_575 . . . ?
O1 C1 C2 N1 -51.0(5) . . . . ?
O2 C1 C2 N1 128.3(4) . . . . ?
O1 C1 C2 C3 67.6(5) . . . . ?
O2 C1 C2 C3 -113.1(4) . . . . ?
N1 C2 C3 C4 -144.2(3) . . . . ?
C1 C2 C3 C4 97.7(4) . . . . ?
Sm1 O3 C4 O4 11.3(4) 3_566 . . . ?
Sm1 O3 C4 C3 -166.7(3) 3_566 . . . ?
Sm1 O4 C4 O3 -138.9(4) 2_546 . . . ?
Sm1 O4 C4 O3 -11.2(4) 3_566 . . . ?
Sm1 O4 C4 C3 39.2(6) 2_546 . . . ?
Sm1 O4 C4 C3 166.9(3) 3_566 . . . ?
Sm1 O4 C4 Sm1 -127.8(4) 2_546 . . 3_566 ?
C2 C3 C4 O3 -9.4(6) . . . . ?
C2 C3 C4 O4 172.5(4) . . . . ?
C2 C3 C4 Sm1 -99.2(14) . . . 3_566 ?
N1 C5 C6 C11 83.9(5) . . . . ?
N1 C5 C6 C7 -98.2(5) . . . . ?
C11 C6 C7 C8 1.2(7) . . . . ?
C5 C6 C7 C8 -176.8(4) . . . . ?
C6 C7 C8 C9 0.7(7) . . . . ?
C7 C8 C9 C10 -1.8(7) . . . . ?
C7 C8 C9 C12 -178.9(4) . . . . ?
C8 C9 C10 C11 1.1(7) . . . . ?
C12 C9 C10 C11 178.2(4) . . . . ?
C7 C6 C11 C10 -1.8(7) . . . . ?
C5 C6 C11 C10 176.1(4) . . . . ?
C9 C10 C11 C6 0.7(7) . . . . ?
Sm1 O6 C12 O5 -2.0(4) 3_667 . . . ?
Sm1 O6 C12 C9 176.0(3) 3_667 . . . ?
Sm1 O5 C12 O6 -126.9(6) 2_646 . . . ?
Sm1 O5 C12 O6 1.7(4) 3_667 . . . ?
Sm1 O5 C12 C9 55.2(9) 2_646 . . . ?
Sm1 O5 C12 C9 -176.2(3) 3_667 . . . ?
Sm1 O5 C12 Sm1 -128.7(7) 2_646 . . 3_667 ?
C10 C9 C12 O6 -154.8(4) . . . . ?
C8 C9 C12 O6 22.2(6) . . . . ?
C10 C9 C12 O5 23.1(6) . . . . ?
C8 C9 C12 O5 -159.8(4) . . . . ?
C6 C5 N1 C2 178.5(4) . . . . ?
C3 C2 N1 C5 169.9(4) . . . . ?
C1 C2 N1 C5 -68.2(4) . . . . ?

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 H7B O3 0.82 2.39 3.105(5) 147.0 1_556
O7 H7B O2 0.82 2.53 3.039(5) 121.1 1_556
O7 H7A Cl1 0.82 2.56 3.175(4) 133.3 4_566
N1 H1B Cl1 0.89 2.19 3.058(3) 163.6 .
N1 H1A Cl1 0.89 2.41 3.226(4) 152.2 4_566

_refine_diff_density_max         1.567
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.123



####################################################################### 
# 
# 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_ZYT_13
_database_code_depnum_ccdc_archive 'CCDC 2236708'
loop_
_audit_author_name
_audit_author_address
'Yatong Zhang'
;Shanxi University Institute of Molecular Science
China
;
_audit_update_record             
;
2023-01-17 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H13 N O7 Tb, Cl'
_chemical_formula_sum            'C12 H13 Cl N O7 Tb'
_chemical_formula_weight         477.60

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'
Cl Cl 0.1484 0.1585 '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                   14.365(6)
_cell_length_b                   12.378(5)
_cell_length_c                   7.859(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.858(11)
_cell_angle_gamma                90
_cell_volume                     1390.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2460
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      28.25

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.282
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    5.315
_shelx_estimated_absorpt_T_min   0.258
_shelx_estimated_absorpt_T_max   0.402
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4143
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microsource'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8566
_diffrn_reflns_av_unetI/netI     0.0768
_diffrn_reflns_av_R_equivalents  0.1142
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.851
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2548
_reflns_number_gt                1976
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0331P)²+25.7907P] 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         2548
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1354
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
Tb1 Tb 0.13833(4) 0.70128(4) 0.86725(7) 0.02670(19) Uani 1 1 d . . . . .
O1 O 0.1609(7) 0.5617(7) 0.6714(11) 0.046(2) Uani 1 1 d . . . . .
O2 O 0.1417(7) 0.6020(7) 0.3950(11) 0.049(3) Uani 1 1 d . . . . .
O3 O 0.0196(7) 0.3627(9) 0.2446(12) 0.055(3) Uani 1 1 d . . . . .
O4 O -0.0420(6) 0.2481(7) 0.4081(11) 0.038(2) Uani 1 1 d . . . . .
O5 O 0.7564(6) 0.2706(8) 0.8319(14) 0.048(2) Uani 1 1 d . . . . .
O6 O 0.7163(6) 0.3772(9) 1.0356(12) 0.051(3) Uani 1 1 d . . . . .
O7 O 0.1047(7) 0.5387(7) 1.0196(11) 0.044(2) Uani 1 1 d . . . . .
H7A H 0.1203 0.4886 0.9608 0.066 Uiso 1 1 d R U . . .
H7B H 0.0900 0.5132 1.1090 0.066 Uiso 1 1 d R U . . .
C1 C 0.1563(7) 0.5385(9) 0.5188(14) 0.027(2) Uani 1 1 d . . . . .
C2 C 0.1702(8) 0.4180(9) 0.4801(16) 0.031(3) Uani 1 1 d . . . . .
H2 H 0.1759 0.4090 0.3577 0.037 Uiso 1 1 calc R U . . .
C3 C 0.0925(8) 0.3440(11) 0.5318(15) 0.033(3) Uani 1 1 d . . . . .
H3A H 0.1204 0.2776 0.5785 0.039 Uiso 1 1 calc R U . . .
H3B H 0.0618 0.3789 0.6214 0.039 Uiso 1 1 calc R U . . .
C4 C 0.0215(8) 0.3170(9) 0.3887(15) 0.031(3) Uani 1 1 d . . . . .
C5 C 0.3428(8) 0.4379(11) 0.5149(17) 0.039(3) Uani 1 1 d . . . . .
H5A H 0.3356 0.5157 0.5206 0.047 Uiso 1 1 calc R U . . .
H5B H 0.3452 0.4183 0.3959 0.047 Uiso 1 1 calc R U . . .
C6 C 0.4333(7) 0.4060(11) 0.6152(14) 0.030(3) Uani 1 1 d . . . . .
C7 C 0.4747(9) 0.4730(12) 0.7443(16) 0.041(3) Uani 1 1 d . . . . .
H7 H 0.4430 0.5347 0.7737 0.049 Uiso 1 1 calc R U . . .
C8 C 0.5611(8) 0.4502(11) 0.8297(15) 0.034(3) Uani 1 1 d . . . . .
H8 H 0.5881 0.4965 0.9139 0.041 Uiso 1 1 calc R U . . .
C9 C 0.6063(8) 0.3583(10) 0.7882(14) 0.030(3) Uani 1 1 d . . . . .
C10 C 0.5667(8) 0.2876(10) 0.6661(16) 0.036(3) Uani 1 1 d . . . . .
H10 H 0.5974 0.2240 0.6423 0.043 Uiso 1 1 calc R U . . .
C11 C 0.4789(9) 0.3128(12) 0.5778(16) 0.042(3) Uani 1 1 d . . . . .
H11 H 0.4519 0.2662 0.4941 0.050 Uiso 1 1 calc R U . . .
C12 C 0.6979(9) 0.3334(11) 0.8879(17) 0.037(3) Uani 1 1 d . . . . .
N1 N 0.2598(6) 0.3849(8) 0.5798(12) 0.027(2) Uani 1 1 d . . . . .
H1A H 0.2659 0.3135 0.5736 0.032 Uiso 1 1 calc R U . . .
H1B H 0.2577 0.4023 0.6893 0.032 Uiso 1 1 calc R U . . .
Cl1 Cl 0.2598(3) 0.1427(3) 0.4894(5) 0.0539(9) 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 O1 2.358(9) . ?
Tb1 O6 2.358(10) 3_667 ?
Tb1 O7 2.415(9) . ?
Tb1 O4 2.422(9) 2_556 ?
Tb1 O5 2.440(10) 2_656 ?
Tb1 O2 2.445(9) 4_576 ?
Tb1 O3 2.478(10) 3_566 ?
Tb1 O4 2.526(9) 3_566 ?
Tb1 O5 2.696(10) 3_667 ?
Tb1 C4 2.903(12) 3_566 ?
Tb1 C12 2.914(13) 3_667 ?
O1 C1 1.229(14) . ?
O2 C1 1.252(14) . ?
O2 Tb1 2.445(9) 4_575 ?
O3 C4 1.264(15) . ?
O3 Tb1 2.478(10) 3_566 ?
O4 C4 1.270(14) . ?
O4 Tb1 2.422(9) 2_546 ?
O4 Tb1 2.526(9) 3_566 ?
O5 C12 1.257(15) . ?
O5 Tb1 2.440(9) 2_646 ?
O5 Tb1 2.696(10) 3_667 ?
O6 C12 1.284(16) . ?
O6 Tb1 2.358(10) 3_667 ?
O7 H7A 0.8184 . ?
O7 H7B 0.8180 . ?
C1 C2 1.539(16) . ?
C2 N1 1.494(13) . ?
C2 C3 1.530(16) . ?
C2 H2 0.9800 . ?
C3 C4 1.477(16) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 Tb1 2.903(12) 3_566 ?
C5 N1 1.496(14) . ?
C5 C6 1.503(15) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C11 1.373(18) . ?
C6 C7 1.395(17) . ?
C7 C8 1.379(18) . ?
C7 H7 0.9300 . ?
C8 C9 1.366(17) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(17) . ?
C9 C12 1.494(17) . ?
C10 C11 1.411(17) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 Tb1 2.914(13) 3_667 ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?

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 O6 74.5(3) . 3_667 ?
O1 Tb1 O7 76.2(3) . . ?
O6 Tb1 O7 73.3(3) 3_667 . ?
O1 Tb1 O4 141.1(3) . 2_556 ?
O6 Tb1 O4 114.5(3) 3_667 2_556 ?
O7 Tb1 O4 71.3(3) . 2_556 ?
O1 Tb1 O5 72.8(3) . 2_656 ?
O6 Tb1 O5 76.5(3) 3_667 2_656 ?
O7 Tb1 O5 141.2(3) . 2_656 ?
O4 Tb1 O5 145.2(3) 2_556 2_656 ?
O1 Tb1 O2 141.7(3) . 4_576 ?
O6 Tb1 O2 111.9(4) 3_667 4_576 ?
O7 Tb1 O2 142.1(3) . 4_576 ?
O4 Tb1 O2 72.8(3) 2_556 4_576 ?
O5 Tb1 O2 72.5(3) 2_656 4_576 ?
O1 Tb1 O3 73.5(4) . 3_566 ?
O6 Tb1 O3 137.0(4) 3_667 3_566 ?
O7 Tb1 O3 71.8(3) . 3_566 ?
O4 Tb1 O3 76.4(3) 2_556 3_566 ?
O5 Tb1 O3 119.3(3) 2_656 3_566 ?
O2 Tb1 O3 111.0(4) 4_576 3_566 ?
O1 Tb1 O4 73.9(3) . 3_566 ?
O6 Tb1 O4 140.3(3) 3_667 3_566 ?
O7 Tb1 O4 120.8(3) . 3_566 ?
O4 Tb1 O4 105.2(3) 2_556 3_566 ?
O5 Tb1 O4 71.6(3) 2_656 3_566 ?
O2 Tb1 O4 80.4(3) 4_576 3_566 ?
O3 Tb1 O4 51.2(3) 3_566 3_566 ?
O1 Tb1 O5 124.4(3) . 3_667 ?
O6 Tb1 O5 51.0(3) 3_667 3_667 ?
O7 Tb1 O5 78.2(3) . 3_667 ?
O4 Tb1 O5 68.9(3) 2_556 3_667 ?
O5 Tb1 O5 100.9(3) 2_656 3_667 ?
O2 Tb1 O5 77.8(3) 4_576 3_667 ?
O3 Tb1 O5 139.8(3) 3_566 3_667 ?
O4 Tb1 O5 158.2(3) 3_566 3_667 ?
O1 Tb1 C4 69.0(3) . 3_566 ?
O6 Tb1 C4 143.5(3) 3_667 3_566 ?
O7 Tb1 C4 95.4(3) . 3_566 ?
O4 Tb1 C4 93.1(3) 2_556 3_566 ?
O5 Tb1 C4 94.6(3) 2_656 3_566 ?
O2 Tb1 C4 98.4(3) 4_576 3_566 ?
O3 Tb1 C4 25.6(3) 3_566 3_566 ?
O4 Tb1 C4 25.9(3) 3_566 3_566 ?
O5 Tb1 C4 162.0(3) 3_667 3_566 ?
O1 Tb1 C12 99.7(4) . 3_667 ?
O6 Tb1 C12 25.5(3) 3_667 3_667 ?
O7 Tb1 C12 74.9(3) . 3_667 ?
O4 Tb1 C12 92.1(3) 2_556 3_667 ?
O5 Tb1 C12 87.9(3) 2_656 3_667 ?
O2 Tb1 C12 94.6(4) 4_576 3_667 ?
O3 Tb1 C12 146.6(3) 3_566 3_667 ?
O4 Tb1 C12 159.5(3) 3_566 3_667 ?
O5 Tb1 C12 25.5(3) 3_667 3_667 ?
C4 Tb1 C12 166.9(4) 3_566 3_667 ?
C1 O1 Tb1 144.2(8) . . ?
C1 O2 Tb1 134.0(8) . 4_575 ?
C4 O3 Tb1 96.3(7) . 3_566 ?
C4 O4 Tb1 136.0(8) . 2_546 ?
C4 O4 Tb1 93.9(7) . 3_566 ?
Tb1 O4 Tb1 112.4(3) 2_546 3_566 ?
C12 O5 Tb1 157.3(9) . 2_646 ?
C12 O5 Tb1 87.0(8) . 3_667 ?
Tb1 O5 Tb1 106.2(3) 2_646 3_667 ?
C12 O6 Tb1 102.3(8) . 3_667 ?
Tb1 O7 H7A 105.7 . . ?
Tb1 O7 H7B 146.1 . . ?
H7A O7 H7B 107.6 . . ?
O1 C1 O2 126.9(11) . . ?
O1 C1 C2 115.1(10) . . ?
O2 C1 C2 118.0(10) . . ?
N1 C2 C3 108.0(9) . . ?
N1 C2 C1 106.5(9) . . ?
C3 C2 C1 114.5(10) . . ?
N1 C2 H2 109.2 . . ?
C3 C2 H2 109.2 . . ?
C1 C2 H2 109.2 . . ?
C4 C3 C2 113.5(10) . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
O3 C4 O4 117.3(11) . . ?
O3 C4 C3 122.1(11) . . ?
O4 C4 C3 120.6(11) . . ?
O3 C4 Tb1 58.1(7) . 3_566 ?
O4 C4 Tb1 60.2(6) . 3_566 ?
C3 C4 Tb1 168.8(8) . 3_566 ?
N1 C5 C6 112.5(9) . . ?
N1 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N1 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C11 C6 C7 118.5(11) . . ?
C11 C6 C5 121.0(12) . . ?
C7 C6 C5 120.5(12) . . ?
C8 C7 C6 121.8(12) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C9 C8 C7 118.7(12) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 121.5(12) . . ?
C8 C9 C12 117.5(11) . . ?
C10 C9 C12 120.9(11) . . ?
C9 C10 C11 119.1(12) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C6 C11 C10 120.2(12) . . ?
C6 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
O5 C12 O6 119.7(12) . . ?
O5 C12 C9 121.9(12) . . ?
O6 C12 C9 118.4(11) . . ?
O5 C12 Tb1 67.5(7) . 3_667 ?
O6 C12 Tb1 52.3(7) . 3_667 ?
C9 C12 Tb1 170.2(9) . 3_667 ?
C2 N1 C5 112.0(9) . . ?
C2 N1 H1A 109.2 . . ?
C5 N1 H1A 109.2 . . ?
C2 N1 H1B 109.2 . . ?
C5 N1 H1B 109.2 . . ?
H1A N1 H1B 107.9 . . ?

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 O2 8(2) . . . . ?
Tb1 O1 C1 C2 -171.7(10) . . . . ?
Tb1 O2 C1 O1 11(2) 4_575 . . . ?
Tb1 O2 C1 C2 -168.9(8) 4_575 . . . ?
O1 C1 C2 N1 -52.7(13) . . . . ?
O2 C1 C2 N1 127.4(11) . . . . ?
O1 C1 C2 C3 66.6(14) . . . . ?
O2 C1 C2 C3 -113.3(12) . . . . ?
N1 C2 C3 C4 -143.9(10) . . . . ?
C1 C2 C3 C4 97.6(13) . . . . ?
Tb1 O3 C4 O4 11.5(12) 3_566 . . . ?
Tb1 O3 C4 C3 -166.8(10) 3_566 . . . ?
Tb1 O4 C4 O3 -139.4(10) 2_546 . . . ?
Tb1 O4 C4 O3 -11.2(12) 3_566 . . . ?
Tb1 O4 C4 C3 38.9(17) 2_546 . . . ?
Tb1 O4 C4 C3 167.1(10) 3_566 . . . ?
Tb1 O4 C4 Tb1 -128.2(11) 2_546 . . 3_566 ?
C2 C3 C4 O3 -8.7(17) . . . . ?
C2 C3 C4 O4 173.1(11) . . . . ?
C2 C3 C4 Tb1 -96(4) . . . 3_566 ?
N1 C5 C6 C11 84.4(14) . . . . ?
N1 C5 C6 C7 -98.2(14) . . . . ?
C11 C6 C7 C8 2.6(19) . . . . ?
C5 C6 C7 C8 -174.9(12) . . . . ?
C6 C7 C8 C9 -1(2) . . . . ?
C7 C8 C9 C10 -1.3(19) . . . . ?
C7 C8 C9 C12 -177.5(11) . . . . ?
C8 C9 C10 C11 2.3(18) . . . . ?
C12 C9 C10 C11 178.4(11) . . . . ?
C7 C6 C11 C10 -1.5(18) . . . . ?
C5 C6 C11 C10 176.0(11) . . . . ?
C9 C10 C11 C6 -0.9(19) . . . . ?
Tb1 O5 C12 O6 -124(2) 2_646 . . . ?
Tb1 O5 C12 O6 2.7(12) 3_667 . . . ?
Tb1 O5 C12 C9 57(3) 2_646 . . . ?
Tb1 O5 C12 C9 -176.7(11) 3_667 . . . ?
Tb1 O5 C12 Tb1 -127(2) 2_646 . . 3_667 ?
Tb1 O6 C12 O5 -3.1(14) 3_667 . . . ?
Tb1 O6 C12 C9 176.2(9) 3_667 . . . ?
C8 C9 C12 O5 -159.6(12) . . . . ?
C10 C9 C12 O5 24.1(19) . . . . ?
C8 C9 C12 O6 21.0(17) . . . . ?
C10 C9 C12 O6 -155.2(12) . . . . ?
C3 C2 N1 C5 169.0(10) . . . . ?
C1 C2 N1 C5 -67.5(12) . . . . ?
C6 C5 N1 C2 179.5(11) . . . . ?

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
N1 H1B Cl1 0.89 2.42 3.237(10) 152.5 4_566
N1 H1A Cl1 0.89 2.21 3.080(10) 164.4 .
O7 H7A Cl1 0.82 2.57 3.189(10) 133.3 4_566
O7 H7B O2 0.82 2.54 3.046(12) 121.0 1_556
O7 H7B O3 0.82 2.42 3.131(13) 146.4 1_556

_refine_diff_density_max         1.249
_refine_diff_density_min         -1.616
_refine_diff_density_rms         0.235



