# 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_cyj
_database_code_depnum_ccdc_archive 'CCDC 2205210'
loop_
_audit_author_name
_audit_author_address
'Xiao-Gang Yang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2023-09-11 deposited with the CCDC.	2023-09-20 downloaded from the CCDC.
;
_audit_creation_date             2023-09-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 Eu N O13'
_chemical_formula_sum            'C21 H16 Eu N O13'
_chemical_formula_weight         642.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1 Eu1'
_chemical_oxdiff_usercomment     'C1 H1 O1 N1 Eu1'
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'
Eu Eu -0.1578 3.6682 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2334(5)
_cell_length_b                   9.4545(4)
_cell_length_c                   14.1066(7)
_cell_angle_alpha                79.145(4)
_cell_angle_beta                 84.640(4)
_cell_angle_gamma                65.658(4)
_cell_volume                     1101.74(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6372
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0770
_cell_measurement_theta_min      3.7620
_shelx_estimated_absorpt_T_max   0.593
_shelx_estimated_absorpt_T_min   0.485
_exptl_absorpt_coefficient_mu    2.921
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.936
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9817
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.231
_diffrn_reflns_theta_min         3.475
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00   0.00   1.00    2.13    --  -15.84 -38.00-180.00   84
  2  ω    -10.00  40.00   1.00    2.13    --   17.09  77.00 -30.00   50
  3  ω      0.00  42.00   1.00    2.13    --   17.09  77.00-180.00   42
  4  ω    -10.00  24.00   1.00    2.13    --   17.09  77.00 150.00   34
  5  ω    -51.00  72.00   1.00    2.13    --   17.09   0.00-120.00  123
  6  ω    -16.00  44.00   1.00    2.13    --   17.09 -77.00  30.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0127574000
_diffrn_orient_matrix_UB_12      0.0277052000
_diffrn_orient_matrix_UB_13      0.0447059000
_diffrn_orient_matrix_UB_21      -0.0787609000
_diffrn_orient_matrix_UB_22      0.0043305000
_diffrn_orient_matrix_UB_23      0.0023415000
_diffrn_orient_matrix_UB_31      0.0272972000
_diffrn_orient_matrix_UB_32      -0.0786389000
_diffrn_orient_matrix_UB_33      0.0248578000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4619
_reflns_number_total             5007
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.959
_refine_diff_density_min         -0.718
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5007
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0253P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0632
_refine_ls_wR_factor_ref         0.0657
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Rotating group:
 O11(H11A,H11B), O12(H12A,H12B), O13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C8(H8A), C9(H9), C10(H10), C13(H13), C15(H15), C17(H17)
2.c Idealised tetrahedral OH refined as rotating group:
 O8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.72884(2) 0.16662(2) 0.96418(2) 0.01781(6) Uani 1 1 d . . . . .
O1 O 0.2859(3) 0.5866(2) 0.99085(18) 0.0266(6) Uani 1 1 d . . . . .
O2 O 0.1674(3) 0.8014(2) 0.88592(18) 0.0262(6) Uani 1 1 d . . . . .
O3 O 0.2394(3) 0.0819(3) 0.94254(19) 0.0316(6) Uani 1 1 d . . . . .
O4 O -0.0139(3) 0.1466(3) 0.9190(2) 0.0316(6) Uani 1 1 d . . . . .
O5 O 0.6387(3) 0.3441(3) 0.8250(2) 0.0345(7) Uani 1 1 d . . . . .
O6 O 0.5199(3) 0.2709(3) 0.7255(2) 0.0377(7) Uani 1 1 d . . . . .
O7 O 0.6444(3) 0.8689(3) 0.7703(2) 0.0403(7) Uani 1 1 d . . . . .
O8 O 0.5178(4) 1.0397(3) 0.6420(2) 0.0460(8) Uani 1 1 d . . . . .
H8 H 0.5461 1.0982 0.6643 0.069 Uiso 1 1 calc GR . . . .
O9 O -0.0954(3) 0.6233(3) 0.65168(18) 0.0316(6) Uani 1 1 d . . . . .
O10 O 0.2818(3) 0.7742(3) 0.47558(18) 0.0348(7) Uani 1 1 d . . . . .
O11 O 0.4858(3) 0.2734(3) 1.06063(19) 0.0305(6) Uani 1 1 d . . . . .
H11A H 0.4545 0.2005 1.0838 0.046 Uiso 1 1 d GR . . . .
H11B H 0.4109 0.3396 1.0238 0.046 Uiso 1 1 d GR . . . .
O12 O 0.5277(3) 0.1033(3) 0.90337(19) 0.0298(6) Uani 1 1 d . . . . .
H12A H 0.4436 0.1273 0.9416 0.045 Uiso 1 1 d GR . . . .
H12B H 0.5603 0.0013 0.9066 0.045 Uiso 1 1 d GR . . . .
O13 O 0.8475(3) -0.0102(3) 0.8452(2) 0.0337(6) Uani 1 1 d . . . . .
H13A H 0.7864 -0.0561 0.8371 0.051 Uiso 1 1 d GR . . . .
H13B H 0.9341 -0.0876 0.8675 0.051 Uiso 1 1 d GR . . . .
N1 N 0.0939(3) 0.6993(3) 0.5653(2) 0.0265(7) Uani 1 1 d . . . . .
C1 C 0.1453(4) 0.5676(4) 0.8631(2) 0.0196(7) Uani 1 1 d . . . . .
C2 C 0.1611(4) 0.4166(3) 0.9051(2) 0.0204(7) Uani 1 1 d . . . . .
H2 H 0.2208 0.3666 0.9605 0.025 Uiso 1 1 calc R . . . .
C3 C 0.0879(4) 0.3400(3) 0.8643(3) 0.0200(7) Uani 1 1 d . . . . .
C4 C 0.0025(4) 0.4136(4) 0.7802(3) 0.0239(8) Uani 1 1 d . . . . .
H4 H -0.0507 0.3652 0.7545 0.029 Uiso 1 1 calc R . . . .
C5 C -0.0036(4) 0.5597(4) 0.7344(3) 0.0227(7) Uani 1 1 d . . . . .
C6 C 0.0665(4) 0.6377(4) 0.7754(3) 0.0231(7) Uani 1 1 d . . . . .
H6 H 0.0613 0.7358 0.7448 0.028 Uiso 1 1 calc R . . . .
C7 C -0.0441(4) 0.6892(4) 0.5677(3) 0.0264(8) Uani 1 1 d . . . . .
C8 C -0.1439(4) 0.7383(4) 0.4898(3) 0.0353(9) Uani 1 1 d . . . . .
H8A H -0.2399 0.7272 0.4946 0.042 Uiso 1 1 calc R . . . .
C9 C -0.0934(5) 0.8049(5) 0.4046(3) 0.0399(10) Uani 1 1 d . . . . .
H9 H -0.1578 0.8420 0.3507 0.048 Uiso 1 1 calc R . . . .
C10 C 0.0509(5) 0.8167(4) 0.3984(3) 0.0357(9) Uani 1 1 d . . . . .
H10 H 0.0870 0.8600 0.3413 0.043 Uiso 1 1 calc R . . . .
C11 C 0.1395(4) 0.7614(4) 0.4813(3) 0.0284(8) Uani 1 1 d . . . . .
C12 C 0.5172(4) 0.5290(4) 0.6892(3) 0.0221(7) Uani 1 1 d . . . . .
C13 C 0.5654(4) 0.6364(4) 0.7168(2) 0.0221(7) Uani 1 1 d . . . . .
H13 H 0.6301 0.6067 0.7700 0.026 Uiso 1 1 calc R . . . .
C14 C 0.5169(4) 0.7872(4) 0.6651(3) 0.0238(8) Uani 1 1 d . . . . .
C15 C 0.4198(4) 0.8320(4) 0.5856(3) 0.0270(8) Uani 1 1 d . . . . .
H15 H 0.3862 0.9337 0.5510 0.032 Uiso 1 1 calc R . . . .
C16 C 0.3742(4) 0.7240(4) 0.5586(2) 0.0253(8) Uani 1 1 d . . . . .
C17 C 0.4232(4) 0.5717(4) 0.6091(3) 0.0257(8) Uani 1 1 d . . . . .
H17 H 0.3933 0.4992 0.5895 0.031 Uiso 1 1 calc R . . . .
C18 C 0.2055(4) 0.6560(4) 0.9150(3) 0.0211(7) Uani 1 1 d . . . . .
C19 C 0.1039(4) 0.1802(4) 0.9111(2) 0.0204(7) Uani 1 1 d . . . . .
C20 C 0.5622(4) 0.3680(4) 0.7498(3) 0.0248(8) Uani 1 1 d . . . . .
C21 C 0.5672(4) 0.9003(4) 0.6982(3) 0.0282(8) 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 2.479(2) 2_667 ?
Eu1 O2 2.518(2) 2_667 ?
Eu1 O3 2.383(2) 2_657 ?
Eu1 O4 2.340(2) 1_655 ?
Eu1 O5 2.297(2) . ?
Eu1 O11 2.447(3) . ?
Eu1 O12 2.439(2) . ?
Eu1 O13 2.453(3) . ?
Eu1 C18 2.863(3) 2_667 ?
Eu1 C19 3.224(3) 2_657 ?
O1 Eu1 2.479(2) 2_667 ?
O1 C18 1.269(4) . ?
O2 Eu1 2.518(2) 2_667 ?
O2 C18 1.264(4) . ?
O3 Eu1 2.383(2) 2_657 ?
O3 C19 1.271(4) . ?
O4 Eu1 2.340(2) 1_455 ?
O4 C19 1.243(4) . ?
O5 C20 1.262(4) . ?
O6 C20 1.247(4) . ?
O7 C21 1.216(4) . ?
O8 H8 0.8200 . ?
O8 C21 1.323(4) . ?
O9 C5 1.394(4) . ?
O9 C7 1.370(4) . ?
O10 C11 1.362(4) . ?
O10 C16 1.403(4) . ?
O11 H11A 0.8527 . ?
O11 H11B 0.8530 . ?
O12 H12A 0.8767 . ?
O12 H12B 0.8776 . ?
O13 H13A 0.8673 . ?
O13 H13B 0.8670 . ?
N1 C7 1.314(4) . ?
N1 C11 1.333(5) . ?
C1 C2 1.391(4) . ?
C1 C6 1.401(5) . ?
C1 C18 1.493(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.394(4) . ?
C3 C4 1.387(4) . ?
C3 C19 1.483(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.391(4) . ?
C5 C6 1.386(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.384(5) . ?
C8 H8A 0.9300 . ?
C8 C9 1.382(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.377(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.380(5) . ?
C12 C13 1.391(4) . ?
C12 C17 1.384(4) . ?
C12 C20 1.509(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(4) . ?
C14 C15 1.392(5) . ?
C14 C21 1.487(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.377(5) . ?
C16 C17 1.387(4) . ?
C17 H17 0.9300 . ?
C18 Eu1 2.863(3) 2_667 ?
C19 Eu1 3.224(3) 2_657 ?

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 O2 52.31(7) 2_667 2_667 ?
O1 Eu1 C18 26.25(8) 2_667 2_667 ?
O1 Eu1 C19 125.36(8) 2_667 2_657 ?
O2 Eu1 C18 26.18(7) 2_667 2_667 ?
O2 Eu1 C19 73.06(7) 2_667 2_657 ?
O3 Eu1 O1 132.31(9) 2_657 2_667 ?
O3 Eu1 O2 82.56(8) 2_657 2_667 ?
O3 Eu1 O11 85.42(8) 2_657 . ?
O3 Eu1 O12 75.66(8) 2_657 . ?
O3 Eu1 O13 78.20(9) 2_657 . ?
O3 Eu1 C18 108.12(9) 2_657 2_667 ?
O3 Eu1 C19 19.81(7) 2_657 2_657 ?
O4 Eu1 O1 80.37(8) 1_655 2_667 ?
O4 Eu1 O2 76.33(9) 1_655 2_667 ?
O4 Eu1 O3 105.72(8) 1_655 2_657 ?
O4 Eu1 O11 150.03(9) 1_655 . ?
O4 Eu1 O12 136.92(9) 1_655 . ?
O4 Eu1 O13 68.66(8) 1_655 . ?
O4 Eu1 C18 75.20(9) 1_655 2_667 ?
O4 Eu1 C19 86.45(8) 1_655 2_657 ?
O5 Eu1 O1 77.82(8) . 2_667 ?
O5 Eu1 O2 129.36(8) . 2_667 ?
O5 Eu1 O3 147.81(9) . 2_657 ?
O5 Eu1 O4 88.44(9) . 1_655 ?
O5 Eu1 O11 96.59(9) . . ?
O5 Eu1 O12 74.42(8) . . ?
O5 Eu1 O13 80.52(9) . . ?
O5 Eu1 C18 103.37(9) . 2_667 ?
O5 Eu1 C19 154.80(9) . 2_657 ?
O11 Eu1 O1 71.96(8) . 2_667 ?
O11 Eu1 O2 77.73(8) . 2_667 ?
O11 Eu1 O13 141.31(8) . . ?
O11 Eu1 C18 74.89(9) . 2_667 ?
O11 Eu1 C19 100.11(8) . 2_657 ?
O12 Eu1 O1 131.27(8) . 2_667 ?
O12 Eu1 O2 144.07(9) . 2_667 ?
O12 Eu1 O11 72.40(9) . . ?
O12 Eu1 O13 69.66(8) . . ?
O12 Eu1 C18 146.66(9) . 2_667 ?
O12 Eu1 C19 92.79(8) . 2_657 ?
O13 Eu1 O1 142.42(9) . 2_667 ?
O13 Eu1 O2 133.16(8) . 2_667 ?
O13 Eu1 C18 143.57(9) . 2_667 ?
O13 Eu1 C19 74.64(9) . 2_657 ?
C18 Eu1 C19 99.13(8) 2_667 2_657 ?
C18 O1 Eu1 94.01(18) . 2_667 ?
C18 O2 Eu1 92.32(19) . 2_667 ?
C19 O3 Eu1 120.7(2) . 2_657 ?
C19 O4 Eu1 158.0(2) . 1_455 ?
C20 O5 Eu1 141.8(2) . . ?
C21 O8 H8 109.5 . . ?
C7 O9 C5 122.5(3) . . ?
C11 O10 C16 119.0(3) . . ?
Eu1 O11 H11A 109.5 . . ?
Eu1 O11 H11B 109.3 . . ?
H11A O11 H11B 104.4 . . ?
Eu1 O12 H12A 110.1 . . ?
Eu1 O12 H12B 110.9 . . ?
H12A O12 H12B 103.1 . . ?
Eu1 O13 H13A 110.4 . . ?
Eu1 O13 H13B 110.0 . . ?
H13A O13 H13B 103.7 . . ?
C7 N1 C11 116.8(3) . . ?
C2 C1 C6 119.7(3) . . ?
C2 C1 C18 119.4(3) . . ?
C6 C1 C18 120.8(3) . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.3(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C19 119.5(3) . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 C19 120.9(3) . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 O9 114.9(3) . . ?
C6 C5 O9 124.3(3) . . ?
C6 C5 C4 120.5(3) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 H6 120.3 . . ?
O9 C7 C8 116.0(3) . . ?
N1 C7 O9 119.3(3) . . ?
N1 C7 C8 124.7(3) . . ?
C7 C8 H8A 121.7 . . ?
C9 C8 C7 116.6(3) . . ?
C9 C8 H8A 121.7 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 121.7 . . ?
C9 C10 C11 116.7(4) . . ?
C11 C10 H10 121.7 . . ?
O10 C11 C10 116.8(3) . . ?
N1 C11 O10 118.8(3) . . ?
N1 C11 C10 124.4(3) . . ?
C13 C12 C20 119.4(3) . . ?
C17 C12 C13 120.3(3) . . ?
C17 C12 C20 120.3(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 120.1(3) . . ?
C13 C14 C21 118.5(3) . . ?
C15 C14 C21 121.3(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.3(3) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 O10 116.6(3) . . ?
C15 C16 C17 121.2(3) . . ?
C17 C16 O10 122.1(3) . . ?
C12 C17 C16 119.1(3) . . ?
C12 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
O1 C18 Eu1 59.74(16) . 2_667 ?
O1 C18 C1 119.6(3) . . ?
O2 C18 Eu1 61.50(17) . 2_667 ?
O2 C18 O1 120.8(3) . . ?
O2 C18 C1 119.4(3) . . ?
C1 C18 Eu1 169.8(2) . 2_667 ?
O3 C19 Eu1 39.44(14) . 2_657 ?
O3 C19 C3 118.1(3) . . ?
O4 C19 Eu1 82.98(18) . 2_657 ?
O4 C19 O3 122.2(3) . . ?
O4 C19 C3 119.8(3) . . ?
C3 C19 Eu1 156.8(2) . 2_657 ?
O5 C20 C12 115.5(3) . . ?
O6 C20 O5 124.6(3) . . ?
O6 C20 C12 119.8(3) . . ?
O7 C21 O8 123.1(3) . . ?
O7 C21 C14 123.5(3) . . ?
O8 C21 C14 113.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.083
_oxdiff_exptl_absorpt_empirical_full_min 0.767
####################################################################### 
# 
# 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_cyj-gd-mof_auto
_database_code_depnum_ccdc_archive 'CCDC 2205212'
loop_
_audit_author_name
_audit_author_address
'Xiao-Gang Yang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2023-09-11 deposited with the CCDC.	2023-09-20 downloaded from the CCDC.
;
_audit_creation_date             2023-09-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 Gd N O13'
_chemical_formula_sum            'C21 H16 Gd N O13'
_chemical_formula_weight         647.60
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     'C1 H1 O1 N1 Gd1'
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'
Gd Gd -0.1653 3.9035 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2225(5)
_cell_length_b                   9.4553(5)
_cell_length_c                   14.1239(6)
_cell_angle_alpha                79.147(4)
_cell_angle_beta                 84.538(4)
_cell_angle_gamma                65.581(5)
_cell_volume                     1101.19(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5850
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6710
_cell_measurement_theta_min      4.0280
_shelx_estimated_absorpt_T_max   0.655
_shelx_estimated_absorpt_T_min   0.537
_exptl_absorpt_coefficient_mu    3.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.953
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             634
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9374
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.021
_diffrn_reflns_theta_min         3.223
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00  22.00   1.00    3.02    --  -15.84  77.00  90.00   65
  2  ω    -42.00  11.00   1.00    3.02    --  -15.84 -77.00 150.00   53
  3  ω    -33.00   3.00   1.00    3.02    --  -15.84 -77.00 -60.00   36
  4  ω    -17.00  11.00   1.00    3.02    --  -15.84 -77.00 -30.00   28
  5  ω    -24.00  83.00   1.00    3.02    --   16.78   0.00-120.00  107
  6  ω     -2.00  86.00   1.00    3.02    --   16.78  38.00 -60.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0526419000
_diffrn_orient_matrix_UB_12      -0.0386668000
_diffrn_orient_matrix_UB_13      0.0071112000
_diffrn_orient_matrix_UB_21      0.0612278000
_diffrn_orient_matrix_UB_22      -0.0693313000
_diffrn_orient_matrix_UB_23      0.0230440000
_diffrn_orient_matrix_UB_31      -0.0248410000
_diffrn_orient_matrix_UB_32      0.0259580000
_diffrn_orient_matrix_UB_33      0.0451013000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4582
_reflns_number_total             4959
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.741
_refine_diff_density_min         -0.785
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4959
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0293
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0231P)²+0.1485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0626
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Rotating group:
 O11(H11A,H11B), O12(H12A,H12B), O13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C8(H8A), C9(H9), C10(H10), C13(H13), C15(H15), C17(H17)
2.c Idealised tetrahedral OH refined as rotating group:
 O8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Gd1 Gd 0.72796(2) 0.16701(2) 0.96422(2) 0.01667(6) Uani 1 1 d . . . . .
O1 O 0.2862(3) 0.5872(3) 0.99082(16) 0.0247(5) Uani 1 1 d . . . . .
O2 O 0.1674(3) 0.8021(3) 0.88696(16) 0.0254(5) Uani 1 1 d . . . . .
O3 O 0.2376(3) 0.0819(3) 0.94324(18) 0.0295(6) Uani 1 1 d . . . . .
O4 O -0.0163(3) 0.1471(3) 0.91920(18) 0.0311(6) Uani 1 1 d . . . . .
O5 O 0.6372(3) 0.3452(3) 0.82626(17) 0.0325(6) Uani 1 1 d . . . . .
O6 O 0.5191(3) 0.2705(3) 0.72644(18) 0.0348(7) Uani 1 1 d . . . . .
O7 O 0.6438(4) 0.8690(3) 0.77111(18) 0.0375(7) Uani 1 1 d . . . . .
O8 O 0.5186(4) 1.0400(3) 0.64192(19) 0.0470(8) Uani 1 1 d . . . . .
H8 H 0.5361 1.1022 0.6676 0.071 Uiso 1 1 calc GR . . . .
O9 O -0.0964(3) 0.6237(3) 0.65274(17) 0.0303(6) Uani 1 1 d . . . . .
O10 O 0.2831(3) 0.7732(3) 0.47580(16) 0.0334(6) Uani 1 1 d . . . . .
O11 O 0.4864(3) 0.2732(3) 1.06096(16) 0.0281(6) Uani 1 1 d . . . . .
H11A H 0.4385 0.2106 1.0701 0.042 Uiso 1 1 d GR . . . .
H11B H 0.4195 0.3586 1.0290 0.042 Uiso 1 1 d GR . . . .
O12 O 0.5283(3) 0.1022(3) 0.90475(17) 0.0293(6) Uani 1 1 d . . . . .
H12A H 0.4426 0.1328 0.9402 0.044 Uiso 1 1 d GR . . . .
H12B H 0.5588 0.0010 0.9127 0.044 Uiso 1 1 d GR . . . .
O13 O 0.8468(3) -0.0088(3) 0.84500(17) 0.0317(6) Uani 1 1 d . . . . .
H13A H 0.7890 -0.0596 0.8396 0.048 Uiso 1 1 d GR . . . .
H13B H 0.9370 -0.0828 0.8654 0.048 Uiso 1 1 d GR . . . .
N1 N 0.0942(4) 0.6991(3) 0.56560(19) 0.0258(7) Uani 1 1 d . . . . .
C1 C 0.1455(4) 0.5681(4) 0.8628(2) 0.0187(7) Uani 1 1 d . . . . .
C2 C 0.1604(4) 0.4176(4) 0.9055(2) 0.0209(7) Uani 1 1 d . . . . .
H2 H 0.2189 0.3682 0.9613 0.025 Uiso 1 1 calc R . . . .
C3 C 0.0873(4) 0.3409(4) 0.8644(2) 0.0182(7) Uani 1 1 d . . . . .
C4 C 0.0006(4) 0.4149(4) 0.7807(2) 0.0218(7) Uani 1 1 d . . . . .
H4 H -0.0540 0.3674 0.7554 0.026 Uiso 1 1 calc R . . . .
C5 C -0.0040(4) 0.5597(4) 0.7352(2) 0.0223(7) Uani 1 1 d . . . . .
C6 C 0.0664(4) 0.6386(4) 0.7759(2) 0.0218(7) Uani 1 1 d . . . . .
H6 H 0.0607 0.7370 0.7456 0.026 Uiso 1 1 calc R . . . .
C7 C -0.0445(4) 0.6888(4) 0.5679(2) 0.0240(7) Uani 1 1 d . . . . .
C8 C -0.1452(5) 0.7375(5) 0.4904(3) 0.0341(9) Uani 1 1 d . . . . .
H8A H -0.2415 0.7265 0.4956 0.041 Uiso 1 1 calc R . . . .
C9 C -0.0942(5) 0.8036(5) 0.4046(3) 0.0372(10) Uani 1 1 d . . . . .
H9 H -0.1585 0.8405 0.3508 0.045 Uiso 1 1 calc R . . . .
C10 C 0.0516(5) 0.8149(5) 0.3984(3) 0.0334(9) Uani 1 1 d . . . . .
H10 H 0.0883 0.8571 0.3412 0.040 Uiso 1 1 calc R . . . .
C11 C 0.1394(5) 0.7605(4) 0.4813(2) 0.0273(8) Uani 1 1 d . . . . .
C12 C 0.5161(4) 0.7872(4) 0.6651(2) 0.0221(7) Uani 1 1 d . . . . .
C13 C 0.5651(4) 0.6360(4) 0.7172(2) 0.0213(7) Uani 1 1 d . . . . .
H13 H 0.6299 0.6065 0.7702 0.026 Uiso 1 1 calc R . . . .
C14 C 0.5169(4) 0.5285(4) 0.6896(2) 0.0203(7) Uani 1 1 d . . . . .
C15 C 0.4244(4) 0.5701(4) 0.6093(2) 0.0244(8) Uani 1 1 d . . . . .
H15 H 0.3956 0.4972 0.5892 0.029 Uiso 1 1 calc R . . . .
C16 C 0.3751(4) 0.7232(4) 0.5589(2) 0.0240(8) Uani 1 1 d . . . . .
C17 C 0.4196(4) 0.8322(4) 0.5858(2) 0.0254(8) Uani 1 1 d . . . . .
H17 H 0.3855 0.9340 0.5514 0.031 Uiso 1 1 calc R . . . .
C18 C 0.2059(4) 0.6563(4) 0.9157(2) 0.0201(7) Uani 1 1 d . . . . .
C19 C 0.1025(4) 0.1802(4) 0.9119(2) 0.0190(7) Uani 1 1 d . . . . .
C20 C 0.5614(4) 0.3685(4) 0.7501(2) 0.0238(7) Uani 1 1 d . . . . .
C21 C 0.5669(5) 0.9017(4) 0.6984(3) 0.0281(8) 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
Gd1 O1 2.473(2) 2_667 ?
Gd1 O2 2.507(2) 2_667 ?
Gd1 O3 2.377(2) 2_657 ?
Gd1 O4 2.323(2) 1_655 ?
Gd1 O5 2.290(2) . ?
Gd1 O11 2.434(2) . ?
Gd1 O12 2.428(2) . ?
Gd1 O13 2.449(2) . ?
Gd1 C18 2.854(3) 2_667 ?
O1 Gd1 2.473(2) 2_667 ?
O1 C18 1.261(4) . ?
O2 Gd1 2.507(2) 2_667 ?
O2 C18 1.266(4) . ?
O3 Gd1 2.377(2) 2_657 ?
O3 C19 1.267(4) . ?
O4 Gd1 2.323(2) 1_455 ?
O4 C19 1.248(4) . ?
O5 C20 1.274(4) . ?
O6 C20 1.250(4) . ?
O7 C21 1.221(4) . ?
O8 H8 0.8200 . ?
O8 C21 1.319(4) . ?
O9 C5 1.394(4) . ?
O9 C7 1.378(4) . ?
O10 C11 1.373(4) . ?
O10 C16 1.404(4) . ?
O11 H11A 0.8601 . ?
O11 H11B 0.8602 . ?
O12 H12A 0.8656 . ?
O12 H12B 0.8659 . ?
O13 H13A 0.8690 . ?
O13 H13B 0.8679 . ?
N1 C7 1.320(4) . ?
N1 C11 1.331(4) . ?
C1 C2 1.393(4) . ?
C1 C6 1.394(5) . ?
C1 C18 1.504(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.398(4) . ?
C3 C4 1.391(5) . ?
C3 C19 1.496(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(5) . ?
C5 C6 1.395(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.387(5) . ?
C8 H8A 0.9300 . ?
C8 C9 1.390(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.386(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.380(5) . ?
C12 C13 1.386(5) . ?
C12 C17 1.387(5) . ?
C12 C21 1.506(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(4) . ?
C14 C15 1.382(5) . ?
C14 C20 1.501(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.392(5) . ?
C16 C17 1.378(5) . ?
C17 H17 0.9300 . ?
C18 Gd1 2.854(3) 2_667 ?

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 Gd1 O2 52.35(7) 2_667 2_667 ?
O1 Gd1 C18 26.15(9) 2_667 2_667 ?
O2 Gd1 C18 26.31(8) 2_667 2_667 ?
O3 Gd1 O1 132.31(8) 2_657 2_667 ?
O3 Gd1 O2 82.38(8) 2_657 2_667 ?
O3 Gd1 O11 85.84(9) 2_657 . ?
O3 Gd1 O12 75.57(9) 2_657 . ?
O3 Gd1 O13 78.14(9) 2_657 . ?
O3 Gd1 C18 108.10(9) 2_657 2_667 ?
O4 Gd1 O1 80.19(8) 1_655 2_667 ?
O4 Gd1 O2 76.10(8) 1_655 2_667 ?
O4 Gd1 O3 105.23(9) 1_655 2_657 ?
O4 Gd1 O11 149.78(8) 1_655 . ?
O4 Gd1 O12 136.98(8) 1_655 . ?
O4 Gd1 O13 68.58(8) 1_655 . ?
O4 Gd1 C18 75.05(9) 1_655 2_667 ?
O5 Gd1 O1 77.62(8) . 2_667 ?
O5 Gd1 O2 129.19(8) . 2_667 ?
O5 Gd1 O3 148.20(9) . 2_657 ?
O5 Gd1 O4 88.53(10) . 1_655 ?
O5 Gd1 O11 96.55(9) . . ?
O5 Gd1 O12 74.97(9) . . ?
O5 Gd1 O13 80.67(9) . . ?
O5 Gd1 C18 103.08(9) . 2_667 ?
O11 Gd1 O1 71.95(8) . 2_667 ?
O11 Gd1 O2 77.70(8) . 2_667 ?
O11 Gd1 O13 141.63(8) . . ?
O11 Gd1 C18 74.79(9) . 2_667 ?
O12 Gd1 O1 131.75(9) . 2_667 ?
O12 Gd1 O2 143.98(8) . 2_667 ?
O12 Gd1 O11 72.66(8) . . ?
O12 Gd1 O13 69.66(8) . . ?
O12 Gd1 C18 146.88(9) . 2_667 ?
O13 Gd1 O1 142.16(8) . 2_667 ?
O13 Gd1 O2 132.95(9) . 2_667 ?
O13 Gd1 C18 143.36(9) . 2_667 ?
C18 O1 Gd1 94.08(19) . 2_667 ?
C18 O2 Gd1 92.3(2) . 2_667 ?
C19 O3 Gd1 121.4(2) . 2_657 ?
C19 O4 Gd1 157.9(2) . 1_455 ?
C20 O5 Gd1 141.6(2) . . ?
C21 O8 H8 109.5 . . ?
C7 O9 C5 122.6(3) . . ?
C11 O10 C16 119.0(3) . . ?
Gd1 O11 H11A 110.0 . . ?
Gd1 O11 H11B 109.7 . . ?
H11A O11 H11B 104.0 . . ?
Gd1 O12 H12A 109.7 . . ?
Gd1 O12 H12B 110.2 . . ?
H12A O12 H12B 103.6 . . ?
Gd1 O13 H13A 110.5 . . ?
Gd1 O13 H13B 110.1 . . ?
H13A O13 H13B 103.6 . . ?
C7 N1 C11 116.4(3) . . ?
C2 C1 C6 120.2(3) . . ?
C2 C1 C18 118.6(3) . . ?
C6 C1 C18 121.0(3) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 119.9(3) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C19 119.3(3) . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 C19 120.8(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.2 . . ?
O9 C5 C6 124.0(3) . . ?
C4 C5 O9 114.7(3) . . ?
C4 C5 C6 121.0(3) . . ?
C1 C6 C5 119.1(3) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
O9 C7 C8 115.8(3) . . ?
N1 C7 O9 119.0(3) . . ?
N1 C7 C8 125.2(3) . . ?
C7 C8 H8A 121.9 . . ?
C7 C8 C9 116.2(4) . . ?
C9 C8 H8A 121.9 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(4) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 121.7 . . ?
C11 C10 C9 116.6(3) . . ?
C11 C10 H10 121.7 . . ?
O10 C11 C10 116.8(3) . . ?
N1 C11 O10 118.2(3) . . ?
N1 C11 C10 124.9(4) . . ?
C13 C12 C17 120.6(3) . . ?
C13 C12 C21 118.2(3) . . ?
C17 C12 C21 121.1(3) . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C20 119.4(3) . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 C20 120.1(3) . . ?
C14 C15 H15 120.7 . . ?
C14 C15 C16 118.7(3) . . ?
C16 C15 H15 120.7 . . ?
C15 C16 O10 121.9(3) . . ?
C17 C16 O10 116.3(3) . . ?
C17 C16 C15 121.7(3) . . ?
C12 C17 H17 120.6 . . ?
C16 C17 C12 118.8(3) . . ?
C16 C17 H17 120.6 . . ?
O1 C18 Gd1 59.78(15) . 2_667 ?
O1 C18 O2 120.7(3) . . ?
O1 C18 C1 120.0(3) . . ?
O2 C18 Gd1 61.35(16) . 2_667 ?
O2 C18 C1 119.1(3) . . ?
C1 C18 Gd1 170.2(2) . 2_667 ?
O3 C19 C3 118.0(3) . . ?
O4 C19 O3 122.4(3) . . ?
O4 C19 C3 119.6(3) . . ?
O5 C20 C14 115.5(3) . . ?
O6 C20 O5 124.2(3) . . ?
O6 C20 C14 120.3(3) . . ?
O7 C21 O8 123.8(3) . . ?
O7 C21 C12 122.9(3) . . ?
O8 C21 C12 113.3(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.301
_oxdiff_exptl_absorpt_empirical_full_min 0.933
####################################################################### 
# 
# 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_cyj-tb-mof_auto
_database_code_depnum_ccdc_archive 'CCDC 2205211'
loop_
_audit_author_name
_audit_author_address
'Xiao-Gang Yang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2023-09-11 deposited with the CCDC.	2023-09-20 downloaded from the CCDC.
;
_audit_creation_date             2023-09-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 N O13 Tb'
_chemical_formula_sum            'C21 H16 N O13 Tb'
_chemical_formula_weight         649.27
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     'C1 H1 O1 N1 Tb1'
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'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1936(5)
_cell_length_b                   9.4195(4)
_cell_length_c                   14.1041(6)
_cell_angle_alpha                79.170(4)
_cell_angle_beta                 84.543(4)
_cell_angle_gamma                65.593(5)
_cell_volume                     1092.23(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5860
_cell_measurement_temperature    294.5
_cell_measurement_theta_max      28.6810
_cell_measurement_theta_min      3.8450
_shelx_estimated_absorpt_T_max   0.557
_shelx_estimated_absorpt_T_min   0.351
_exptl_absorpt_coefficient_mu    3.313
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.974
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.846
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9846
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.284
_diffrn_reflns_theta_min         3.483
_diffrn_ambient_temperature      294.5
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.846
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00 -10.00   1.00    2.43    --  -15.84 -57.00 150.00   63
  2  ω     -8.00  19.00   1.00    2.43    --   16.93  77.00 150.00   27
  3  ω    -46.00  33.00   1.00    2.43    --   16.93 -57.00  90.00   79
  4  ω     -9.00  20.00   1.00    2.43    --   16.93  77.00 -30.00   29
  5  ω      4.00  39.00   1.00    2.43    --   16.93  77.00  60.00   35
  6  ω    -50.00  34.00   1.00    2.43    --   16.93 -57.00-150.00   84
  7  ω      3.00  84.00   1.00    2.43    --   16.93  57.00   0.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0326714000
_diffrn_orient_matrix_UB_12      0.0745040000
_diffrn_orient_matrix_UB_13      -0.0303257000
_diffrn_orient_matrix_UB_21      -0.0670070000
_diffrn_orient_matrix_UB_22      -0.0147828000
_diffrn_orient_matrix_UB_23      -0.0082608000
_diffrn_orient_matrix_UB_31      -0.0402897000
_diffrn_orient_matrix_UB_32      0.0354562000
_diffrn_orient_matrix_UB_33      0.0404326000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4612
_reflns_number_total             5045
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.777
_refine_diff_density_rms         0.132
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         5045
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0313
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0172P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0556
_refine_ls_wR_factor_ref         0.0583
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 Tb1-H11A \\sim Tb1-H11B
 with sigma of 0.02
3.a Free rotating group:
 O11(H11A,H11B)
3.b Rotating group:
 O12(H12A,H12B), O13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C8(H8), C15(H15), C17(H17), C13(H13), C6(H6), C4(H4), C2(H2)
3.d Idealised tetrahedral OH refined as rotating group:
 O8(H8A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C9 C -0.0934(4) 0.8018(5) 0.4052(3) 0.0377(10) Uani 1 1 d . . . . .
H9 H -0.1579 0.8383 0.3514 0.045 Uiso 1 1 calc R . . . .
C10 C 0.0518(5) 0.8134(5) 0.3985(3) 0.0343(10) Uani 1 1 d . . . . .
H10 H 0.0882 0.8556 0.3410 0.041 Uiso 1 1 calc R . . . .
C8 C -0.1444(4) 0.7369(5) 0.4907(3) 0.0317(9) Uani 1 1 d . . . . .
H8 H -0.2410 0.7260 0.4958 0.038 Uiso 1 1 calc R . . . .
C11 C 0.1401(4) 0.7598(4) 0.4806(3) 0.0254(8) Uani 1 1 d . . . . .
C7 C -0.0452(4) 0.6891(4) 0.5680(3) 0.0256(8) Uani 1 1 d . . . . .
C16 C 0.3760(4) 0.7215(4) 0.5586(3) 0.0232(8) Uani 1 1 d . . . . .
C15 C 0.4243(4) 0.5701(4) 0.6094(2) 0.0233(8) Uani 1 1 d . . . . .
H15 H 0.3950 0.4969 0.5897 0.028 Uiso 1 1 calc R . . . .
C17 C 0.4200(4) 0.8314(4) 0.5854(3) 0.0240(8) Uani 1 1 d . . . . .
H17 H 0.3855 0.9332 0.5505 0.029 Uiso 1 1 calc R . . . .
C21 C 0.5668(4) 0.9017(4) 0.6985(3) 0.0271(9) Uani 1 1 d . . . . .
C12 C 0.5164(4) 0.7888(4) 0.6653(3) 0.0215(8) Uani 1 1 d . . . . .
C13 C 0.5642(4) 0.6363(4) 0.7181(2) 0.0204(8) Uani 1 1 d . . . . .
H13 H 0.6276 0.6073 0.7719 0.025 Uiso 1 1 calc R . . . .
C14 C 0.5172(4) 0.5280(4) 0.6902(2) 0.0190(7) Uani 1 1 d . . . . .
C20 C 0.5612(4) 0.3674(4) 0.7520(3) 0.0226(8) Uani 1 1 d . . . . .
C5 C -0.0044(4) 0.5608(4) 0.7357(2) 0.0201(8) Uani 1 1 d . . . . .
C6 C 0.0662(4) 0.6387(4) 0.7761(2) 0.0203(8) Uani 1 1 d . . . . .
H6 H 0.0608 0.7372 0.7454 0.024 Uiso 1 1 calc R . . . .
C4 C 0.0006(4) 0.4153(4) 0.7813(2) 0.0210(8) Uani 1 1 d . . . . .
H4 H -0.0543 0.3677 0.7560 0.025 Uiso 1 1 calc R . . . .
C18 C 0.2061(4) 0.6573(4) 0.9159(3) 0.0184(7) Uani 1 1 d . . . . .
C1 C 0.1457(4) 0.5689(4) 0.8632(2) 0.0186(7) Uani 1 1 d . . . . .
C2 C 0.1601(4) 0.4176(4) 0.9060(2) 0.0198(8) Uani 1 1 d . . . . .
H2 H 0.2182 0.3682 0.9621 0.024 Uiso 1 1 calc R . . . .
C3 C 0.0878(4) 0.3406(4) 0.8648(2) 0.0179(7) Uani 1 1 d . . . . .
C19 C 0.1018(4) 0.1804(4) 0.9123(2) 0.0186(7) Uani 1 1 d . . . . .
N1 N 0.0947(3) 0.6989(3) 0.5659(2) 0.0249(7) Uani 1 1 d . . . . .
O10 O 0.2844(3) 0.7715(3) 0.47583(18) 0.0324(6) Uani 1 1 d . . . . .
O9 O -0.0966(3) 0.6251(3) 0.65323(18) 0.0291(6) Uani 1 1 d . . . . .
O8 O 0.5181(4) 1.0409(3) 0.6415(2) 0.0464(8) Uani 1 1 d . . . . .
H8A H 0.5396 1.1023 0.6657 0.070 Uiso 1 1 calc GR . . . .
O7 O 0.6420(3) 0.8710(3) 0.7712(2) 0.0361(7) Uani 1 1 d . . . . .
O6 O 0.5186(3) 0.2703(3) 0.72720(19) 0.0341(7) Uani 1 1 d . . . . .
O5 O 0.6361(3) 0.3448(3) 0.82735(19) 0.0304(6) Uani 1 1 d . . . . .
O1 O 0.1679(3) 0.8037(3) 0.88746(17) 0.0242(6) Uani 1 1 d . . . . .
O2 O 0.2869(3) 0.5873(3) 0.99127(17) 0.0241(6) Uani 1 1 d . . . . .
O3 O 0.2364(3) 0.0811(3) 0.94395(19) 0.0272(6) Uani 1 1 d . . . . .
O4 O -0.0180(3) 0.1483(3) 0.91974(19) 0.0295(6) Uani 1 1 d . . . . .
O11 O 0.4870(3) 0.2727(3) 1.05936(18) 0.0284(6) Uani 1 1 d . . . . .
H11A H 0.4160 0.3668 1.0506 0.043 Uiso 1 1 d DG . . . .
H11B H 0.4496 0.2241 1.1053 0.043 Uiso 1 1 d DG . . . .
O12 O 0.5297(3) 0.0989(3) 0.90726(18) 0.0272(6) Uani 1 1 d . . . . .
H12A H 0.5056 0.1462 0.8497 0.041 Uiso 1 1 d GR . . . .
H12B H 0.4434 0.1358 0.9397 0.041 Uiso 1 1 d GR . . . .
O13 O 0.8461(3) -0.0077(3) 0.84507(18) 0.0310(6) Uani 1 1 d . . . . .
H13A H 0.9412 -0.0706 0.8611 0.046 Uiso 1 1 d GR . . . .
H13B H 0.7972 -0.0679 0.8471 0.046 Uiso 1 1 d GR . . . .
Tb1 Tb 0.72732(2) 0.16726(2) 0.96427(2) 0.01645(6) Uani 1 1 d 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
C9 H9 0.9300 . ?
C9 C10 1.377(5) . ?
C9 C8 1.378(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.369(5) . ?
C8 H8 0.9300 . ?
C8 C7 1.374(5) . ?
C11 N1 1.338(4) . ?
C11 O10 1.371(4) . ?
C7 N1 1.325(4) . ?
C7 O9 1.374(4) . ?
C16 C15 1.378(5) . ?
C16 C17 1.378(5) . ?
C16 O10 1.395(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.385(5) . ?
C17 H17 0.9300 . ?
C17 C12 1.393(5) . ?
C21 C12 1.484(5) . ?
C21 O8 1.324(4) . ?
C21 O7 1.212(5) . ?
C12 C13 1.396(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.390(5) . ?
C14 C20 1.509(5) . ?
C20 O6 1.247(4) . ?
C20 O5 1.258(4) . ?
C5 C6 1.381(5) . ?
C5 C4 1.383(4) . ?
C5 O9 1.392(4) . ?
C6 H6 0.9300 . ?
C6 C1 1.395(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.389(5) . ?
C18 C1 1.499(5) . ?
C18 O1 1.267(4) . ?
C18 O2 1.264(4) . ?
C18 Tb1 2.837(4) 2_667 ?
C1 C2 1.396(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.392(5) . ?
C3 C19 1.489(4) . ?
C19 O3 1.264(4) . ?
C19 O4 1.247(4) . ?
O8 H8A 0.8200 . ?
O5 Tb1 2.273(2) . ?
O1 Tb1 2.488(3) 2_667 ?
O2 Tb1 2.456(2) 2_667 ?
O3 Tb1 2.358(2) 2_657 ?
O4 Tb1 2.308(2) 1_455 ?
O11 H11A 0.8500 . ?
O11 H11B 0.8502 . ?
O11 Tb1 2.407(2) . ?
O12 H12A 0.8500 . ?
O12 H12B 0.8502 . ?
O12 Tb1 2.408(2) . ?
O13 H13A 0.8524 . ?
O13 H13B 0.8524 . ?
O13 Tb1 2.437(2) . ?
Tb1 C18 2.837(4) 2_667 ?
Tb1 O1 2.488(3) 2_667 ?
Tb1 O2 2.456(2) 2_667 ?
Tb1 O3 2.358(2) 2_657 ?
Tb1 O4 2.308(2) 1_655 ?

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
C10 C9 H9 119.6 . . ?
C10 C9 C8 120.8(4) . . ?
C8 C9 H9 119.6 . . ?
C9 C10 H10 121.6 . . ?
C11 C10 C9 116.8(3) . . ?
C11 C10 H10 121.6 . . ?
C9 C8 H8 121.7 . . ?
C7 C8 C9 116.6(4) . . ?
C7 C8 H8 121.7 . . ?
C10 C11 O10 117.7(3) . . ?
N1 C11 C10 124.9(4) . . ?
N1 C11 O10 117.4(3) . . ?
N1 C7 C8 125.1(3) . . ?
N1 C7 O9 118.4(3) . . ?
O9 C7 C8 116.5(3) . . ?
C15 C16 C17 121.5(4) . . ?
C15 C16 O10 122.4(3) . . ?
C17 C16 O10 116.1(3) . . ?
C16 C15 H15 120.4 . . ?
C16 C15 C14 119.3(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C12 119.6(3) . . ?
C12 C17 H17 120.2 . . ?
O8 C21 C12 112.8(4) . . ?
O7 C21 C12 123.6(3) . . ?
O7 C21 O8 123.5(4) . . ?
C17 C12 C21 122.3(3) . . ?
C17 C12 C13 119.4(3) . . ?
C13 C12 C21 118.3(4) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 C20 120.6(3) . . ?
C13 C14 C20 119.1(3) . . ?
O6 C20 C14 119.1(3) . . ?
O6 C20 O5 125.2(3) . . ?
O5 C20 C14 115.7(3) . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 O9 124.0(3) . . ?
C4 C5 O9 114.9(3) . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C1 119.6(3) . . ?
C1 C6 H6 120.2 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 119.9(3) . . ?
C3 C4 H4 120.0 . . ?
C1 C18 Tb1 170.2(2) . 2_667 ?
O1 C18 C1 119.5(3) . . ?
O1 C18 Tb1 61.22(19) . 2_667 ?
O2 C18 C1 119.8(3) . . ?
O2 C18 O1 120.6(3) . . ?
O2 C18 Tb1 59.76(18) . 2_667 ?
C6 C1 C18 121.4(3) . . ?
C6 C1 C2 119.7(3) . . ?
C2 C1 C18 118.8(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 C19 120.9(3) . . ?
C2 C3 C19 119.5(3) . . ?
O3 C19 C3 118.1(3) . . ?
O4 C19 C3 119.6(3) . . ?
O4 C19 O3 122.3(3) . . ?
C7 N1 C11 115.8(3) . . ?
C11 O10 C16 119.4(3) . . ?
C7 O9 C5 123.2(3) . . ?
C21 O8 H8A 109.5 . . ?
C20 O5 Tb1 141.5(2) . . ?
C18 O1 Tb1 92.3(2) . 2_667 ?
C18 O2 Tb1 93.8(2) . 2_667 ?
C19 O3 Tb1 122.4(2) . 2_657 ?
C19 O4 Tb1 158.6(2) . 1_455 ?
H11A O11 H11B 104.5 . . ?
Tb1 O11 H11A 126.7 . . ?
Tb1 O11 H11B 128.6 . . ?
H12A O12 H12B 104.5 . . ?
Tb1 O12 H12A 109.5 . . ?
Tb1 O12 H12B 109.2 . . ?
H13A O13 H13B 104.4 . . ?
Tb1 O13 H13A 109.4 . . ?
Tb1 O13 H13B 109.5 . . ?
O5 Tb1 C18 103.26(10) . 2_667 ?
O5 Tb1 O1 129.59(8) . 2_667 ?
O5 Tb1 O2 77.52(9) . 2_667 ?
O5 Tb1 O3 148.31(10) . 2_657 ?
O5 Tb1 O4 88.70(9) . 1_655 ?
O5 Tb1 O11 96.16(9) . . ?
O5 Tb1 O12 75.76(9) . . ?
O5 Tb1 O13 80.61(9) . . ?
O1 Tb1 C18 26.51(8) 2_667 2_667 ?
O2 Tb1 C18 26.41(8) 2_667 2_667 ?
O2 Tb1 O1 52.81(8) 2_667 2_667 ?
O3 Tb1 C18 107.86(10) 2_657 2_667 ?
O3 Tb1 O1 81.90(8) 2_657 2_667 ?
O3 Tb1 O2 132.40(9) 2_657 2_667 ?
O3 Tb1 O11 86.25(8) 2_657 . ?
O3 Tb1 O12 74.95(9) 2_657 . ?
O3 Tb1 O13 78.14(9) 2_657 . ?
O4 Tb1 C18 74.78(9) 1_655 2_667 ?
O4 Tb1 O1 75.96(8) 1_655 2_667 ?
O4 Tb1 O2 79.96(8) 1_655 2_667 ?
O4 Tb1 O3 104.93(8) 1_655 2_657 ?
O4 Tb1 O11 149.83(9) 1_655 . ?
O4 Tb1 O12 137.38(9) 1_655 . ?
O4 Tb1 O13 68.71(8) 1_655 . ?
O11 Tb1 C18 75.12(9) . 2_667 ?
O11 Tb1 O1 78.10(9) . 2_667 ?
O11 Tb1 O2 72.15(8) . 2_667 ?
O11 Tb1 O12 72.28(9) . . ?
O11 Tb1 O13 141.46(9) . . ?
O12 Tb1 C18 147.04(8) . 2_667 ?
O12 Tb1 O1 143.20(8) . 2_667 ?
O12 Tb1 O2 132.27(8) . 2_667 ?
O12 Tb1 O13 69.70(8) . . ?
O13 Tb1 C18 143.22(8) . 2_667 ?
O13 Tb1 O1 132.77(8) . 2_667 ?
O13 Tb1 O2 141.93(8) . 2_667 ?

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
C9 C10 C11 N1 -0.6(6) . . . . ?
C9 C10 C11 O10 -179.4(3) . . . . ?
C9 C8 C7 N1 -0.9(6) . . . . ?
C9 C8 C7 O9 179.7(3) . . . . ?
C10 C9 C8 C7 1.6(6) . . . . ?
C10 C11 N1 C7 1.3(5) . . . . ?
C10 C11 O10 C16 178.5(3) . . . . ?
C8 C9 C10 C11 -0.9(6) . . . . ?
C8 C7 N1 C11 -0.5(5) . . . . ?
C8 C7 O9 C5 175.1(3) . . . . ?
C16 C15 C14 C13 -1.6(5) . . . . ?
C16 C15 C14 C20 175.1(3) . . . . ?
C16 C17 C12 C21 -179.5(3) . . . . ?
C16 C17 C12 C13 -1.3(5) . . . . ?
C15 C16 C17 C12 0.4(5) . . . . ?
C15 C16 O10 C11 57.1(4) . . . . ?
C15 C14 C20 O6 3.0(5) . . . . ?
C15 C14 C20 O5 -175.2(3) . . . . ?
C17 C16 C15 C14 1.0(5) . . . . ?
C17 C16 O10 C11 -124.8(3) . . . . ?
C17 C12 C13 C14 0.7(5) . . . . ?
C21 C12 C13 C14 178.9(3) . . . . ?
C12 C13 C14 C15 0.8(5) . . . . ?
C12 C13 C14 C20 -176.1(3) . . . . ?
C13 C14 C20 O6 179.8(3) . . . . ?
C13 C14 C20 O5 1.6(4) . . . . ?
C14 C20 O5 Tb1 172.2(2) . . . . ?
C5 C6 C1 C18 -172.2(3) . . . . ?
C5 C6 C1 C2 3.3(5) . . . . ?
C5 C4 C3 C2 4.6(5) . . . . ?
C5 C4 C3 C19 -176.8(3) . . . . ?
C6 C5 C4 C3 -4.9(5) . . . . ?
C6 C5 O9 C7 52.5(5) . . . . ?
C6 C1 C2 C3 -3.6(5) . . . . ?
C4 C5 C6 C1 1.0(5) . . . . ?
C4 C5 O9 C7 -133.3(3) . . . . ?
C4 C3 C19 O3 138.1(3) . . . . ?
C4 C3 C19 O4 -42.0(4) . . . . ?
C18 C1 C2 C3 172.0(3) . . . . ?
C1 C18 O1 Tb1 168.8(2) . . . 2_667 ?
C1 C18 O2 Tb1 -168.7(2) . . . 2_667 ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C1 C2 C3 C19 -178.9(3) . . . . ?
C2 C3 C19 O3 -43.3(4) . . . . ?
C2 C3 C19 O4 136.6(3) . . . . ?
C3 C19 O3 Tb1 173.2(2) . . . 2_657 ?
C3 C19 O4 Tb1 -59.2(8) . . . 1_455 ?
N1 C11 O10 C16 -0.4(5) . . . . ?
N1 C7 O9 C5 -4.3(5) . . . . ?
O10 C11 N1 C7 -179.9(3) . . . . ?
O10 C16 C15 C14 179.0(3) . . . . ?
O10 C16 C17 C12 -177.7(3) . . . . ?
O9 C7 N1 C11 178.9(3) . . . . ?
O9 C5 C6 C1 174.9(3) . . . . ?
O9 C5 C4 C3 -179.4(3) . . . . ?
O8 C21 C12 C17 -3.5(5) . . . . ?
O8 C21 C12 C13 178.3(3) . . . . ?
O7 C21 C12 C17 175.1(3) . . . . ?
O7 C21 C12 C13 -3.1(5) . . . . ?
O6 C20 O5 Tb1 -5.8(6) . . . . ?
O1 C18 C1 C6 8.7(4) . . . . ?
O1 C18 C1 C2 -166.9(3) . . . . ?
O1 C18 O2 Tb1 7.3(3) . . . 2_667 ?
O2 C18 C1 C6 -175.3(3) . . . . ?
O2 C18 C1 C2 9.1(4) . . . . ?
O2 C18 O1 Tb1 -7.2(3) . . . 2_667 ?
O3 C19 O4 Tb1 120.8(6) . . . 1_455 ?
O4 C19 O3 Tb1 -6.8(5) . . . 2_657 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.455
_oxdiff_exptl_absorpt_empirical_full_min 0.592
####################################################################### 
# 
# 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_cyj-230908_auto
_database_code_depnum_ccdc_archive 'CCDC 2266603'
loop_
_audit_author_name
_audit_author_address
'Xiao-Gang Yang'
;Luoyang Normal University
China
;
_audit_update_record             
;
2023-09-18 deposited with the CCDC.	2023-09-20 downloaded from the CCDC.
;
_audit_creation_date             2023-09-16
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C21 H13 N O10, 1[C2H3N]'
_chemical_formula_sum            'C23 H16 N2 O10'
_chemical_formula_weight         480.391
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y,-z+1/2
4 -x+1/2,-y+1/2,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y,z-1/2
8 x-1/2,y-1/2,-z-1/2

_symmetry_Int_Tables_number      60
_cell_length_a                   13.1733(10)
_cell_length_b                   21.389(2)
_cell_length_c                   16.5014(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4649.5(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2610
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.3390
_cell_measurement_theta_min      3.8190
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       block
_exptl_crystal_F_000             1985.666
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.9966
_diffrn_reflns_Laue_measured_fraction_max 0.9966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16118
_diffrn_reflns_point_group_measured_fraction_full 0.9966
_diffrn_reflns_point_group_measured_fraction_max 0.9966
_diffrn_reflns_theta_full        24.9998
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.46
_diffrn_ambient_temperature      293.00
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9966
_diffrn_measured_fraction_theta_max 0.9966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  39.00   1.00   40.00    --   16.78  77.00-180.00   49
  2  ω    -52.00  36.00   1.00   40.00    --   16.78 -19.00 -60.00   88
  3  ω     -2.00  30.00   1.00   40.00    --   16.78  38.00 -60.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              0
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                2402
_reflns_number_total             4084
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.4273
_refine_diff_density_min         -0.5256
_refine_diff_density_rms         0.0930
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             5.8815
_refine_ls_goodness_of_fit_ref   1.0551
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4084
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0818
_refine_ls_restrained_S_all      1.0549
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0969P)²+5.1458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2146
_refine_ls_wR_factor_ref         0.2473
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O3-H3a
 0.82 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
: with sigma of 0.01 and sigma for terminal atoms of 0.02
: with sigma of 0.01 and sigma for terminal atoms of 0.02
: with sigma of 0.01 and sigma for terminal atoms of 0.02
: with sigma of 0.01 and sigma for terminal atoms of 0.02
: with sigma of 0.01 and sigma for terminal atoms of 0.02
: with sigma of 0.01 and sigma for terminal atoms of 0.02
: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: H23a(0.45) H23b(0.45) H23c(0.45) H25a(0.5) H25b(0.5) H25c(0.5)
 H23a(0.5) H23b(0.5) H23c(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C10(H10), C15(H15), C16(H16), C18(H18)
6.b Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
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_refinement_flags_posn
C1 C 0.7571(4) 0.8706(2) 0.5906(3) 0.0698(14) Uani 1.000000 .
H1 H 0.7587(4) 0.9140(2) 0.5931(3) 0.0837(17) Uiso 1.000000 R
C2 C 0.8406(4) 0.8386(2) 0.5617(3) 0.0661(14) Uani 1.000000 .
H2 H 0.8986(4) 0.8596(2) 0.5446(3) 0.0794(16) Uiso 1.000000 R
C3 C 0.6720(3) 0.8392(2) 0.6157(3) 0.0574(12) Uani 1.000000 .
H3 H 0.6149(3) 0.8601(2) 0.6346(3) 0.0689(14) Uiso 1.000000 R
C4 C 0.6759(3) 0.7755(2) 0.6114(2) 0.0414(10) Uani 1.000000 .
C5 C 0.8346(3) 0.77535(19) 0.5591(2) 0.0435(10) Uani 1.000000 .
C6 C 0.9053(3) 0.67734(19) 0.5290(2) 0.0398(10) Uani 1.000000 .
C7 C 0.9012(3) 0.6472(2) 0.4545(2) 0.0441(10) Uani 1.000000 .
H7 H 0.9044(3) 0.6698(2) 0.4065(2) 0.0529(12) Uiso 1.000000 R
C8 C 0.9001(3) 0.6434(2) 0.6014(2) 0.0424(10) Uani 1.000000 .
H8 H 0.9023(3) 0.6640(2) 0.6510(2) 0.0509(12) Uiso 1.000000 R
C9 C 0.8917(3) 0.57933(19) 0.5984(2) 0.0384(9) Uani 1.000000 .
C10 C 0.8876(3) 0.5479(2) 0.5250(2) 0.0400(10) Uani 1.000000 .
H10 H 0.8819(3) 0.5046(2) 0.5238(2) 0.0480(12) Uiso 1.000000 R
C11 C 0.8921(3) 0.5818(2) 0.4535(2) 0.0407(10) Uani 1.000000 .
C12 C 0.8845(3) 0.5480(2) 0.3741(2) 0.0475(11) Uani 1.000000 .
C13 C 0.8843(3) 0.5429(2) 0.6746(2) 0.0405(10) Uani 1.000000 .
C14 C 0.6039(3) 0.67629(18) 0.6343(2) 0.0366(9) Uani 1.000000 .
C15 C 0.6133(3) 0.64553(19) 0.7071(2) 0.0382(9) Uani 1.000000 .
H15 H 0.6143(3) 0.66791(19) 0.7554(2) 0.0459(11) Uiso 1.000000 R
C16 C 0.6029(3) 0.64430(19) 0.5613(2) 0.0403(10) Uani 1.000000 .
H16 H 0.5958(3) 0.66559(19) 0.5125(2) 0.0483(12) Uiso 1.000000 R
C17 C 0.6213(2) 0.58085(19) 0.7079(2) 0.0349(9) Uani 1.000000 .
C18 C 0.6205(3) 0.54825(19) 0.6357(2) 0.0368(9) Uani 1.000000 .
H18 H 0.6253(3) 0.50487(19) 0.6360(2) 0.0441(11) Uiso 1.000000 R
C19 C 0.6126(3) 0.57998(19) 0.5628(2) 0.0366(9) Uani 1.000000 .
C20 C 0.6289(3) 0.5468(2) 0.7857(2) 0.0398(10) Uani 1.000000 .
C21 C 0.6168(3) 0.5439(2) 0.4856(2) 0.0419(10) Uani 1.000000 .
N1 N 0.7542(2) 0.74313(15) 0.58272(18) 0.0411(8) Uani 1.000000 .
O1 O 0.9155(2) 0.74165(13) 0.52950(17) 0.0528(8) Uani 1.000000 .
O2 O 0.5930(2) 0.74123(13) 0.63533(17) 0.0468(7) Uani 1.000000 .
O3 O 0.8940(3) 0.58151(17) 0.31059(19) 0.0710(10) Uani 1.000000 D
O4 O 0.8696(2) 0.49066(15) 0.37399(17) 0.0599(9) Uani 1.000000 .
O5 O 0.8853(2) 0.48518(14) 0.67410(17) 0.0585(9) Uani 1.000000 .
O6 O 0.8764(2) 0.57545(14) 0.74035(17) 0.0586(9) Uani 1.000000 .
H6 H 0.876(4) 0.55192(19) 0.7796(2) 0.0878(13) Uiso 1.000000 GR
O7 O 0.6110(3) 0.57575(15) 0.42030(18) 0.0681(10) Uani 1.000000 .
O8 O 0.6266(2) 0.48624(14) 0.48730(16) 0.0524(8) Uani 1.000000 .
O9 O 0.6348(2) 0.57895(15) 0.85067(17) 0.0535(8) Uani 1.000000 .
O10 O 0.6301(2) 0.48813(15) 0.78508(17) 0.0623(9) Uani 1.000000 .
H3a H 0.898(5) 0.560(3) 0.269(3) 0.14(3) Uiso 1.000000 D
H7a H 0.621(4) 0.552(3) 0.372(4) 0.11(2) Uiso 1.000000 .
H9 H 0.646(6) 0.552(4) 0.894(6) 0.19(4) Uiso 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.380(6) . ?
C1 C3 1.371(6) . ?
C2 H2 0.9300 . ?
C2 C5 1.355(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.364(6) . ?
C4 N1 1.329(5) . ?
C4 O2 1.374(5) . ?
C5 N1 1.322(5) . ?
C5 O1 1.377(5) . ?
C6 C7 1.388(5) . ?
C6 C8 1.399(5) . ?
C6 O1 1.382(5) . ?
C7 H7 0.9300 . ?
C7 C11 1.404(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.376(5) . ?
C9 C10 1.387(5) . ?
C9 C13 1.482(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(5) . ?
C11 C12 1.498(6) . ?
C12 O3 1.276(5) . ?
C12 O4 1.243(5) . ?
C13 O5 1.236(5) . ?
C13 O6 1.293(5) . ?
C14 C15 1.375(5) . ?
C14 C16 1.386(5) . ?
C14 O2 1.397(4) . ?
C15 H15 0.9300 . ?
C15 C17 1.388(5) . ?
C16 H16 0.9300 . ?
C16 C19 1.382(5) . ?
C17 C18 1.381(5) . ?
C17 C20 1.479(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.386(5) . ?
C19 C21 1.490(5) . ?
C20 O9 1.277(4) . ?
C20 O10 1.254(5) . ?
C21 O7 1.277(5) . ?
C21 O8 1.240(5) . ?
O3 H3a 0.820(10) . ?
O6 H6 0.8200 . ?
O7 H7a 0.95(6) . ?
O9 H9 0.94(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.6(3) . . ?
C3 C1 H1 119.6(3) . . ?
C3 C1 C2 120.9(5) . . ?
H2 C2 C1 121.3(3) . . ?
C5 C2 C1 117.3(4) . . ?
C5 C2 H2 121.3(3) . . ?
H3 C3 C1 121.9(3) . . ?
C4 C3 C1 116.2(4) . . ?
C4 C3 H3 121.9(3) . . ?
N1 C4 C3 124.6(4) . . ?
O2 C4 C3 119.2(4) . . ?
O2 C4 N1 116.1(4) . . ?
N1 C5 C2 123.9(4) . . ?
O1 C5 C2 119.2(4) . . ?
O1 C5 N1 116.9(4) . . ?
C8 C6 C7 120.8(4) . . ?
O1 C6 C7 118.2(4) . . ?
O1 C6 C8 121.0(4) . . ?
H7 C7 C6 120.7(2) . . ?
C11 C7 C6 118.5(4) . . ?
C11 C7 H7 120.7(2) . . ?
H8 C8 C6 120.3(2) . . ?
C9 C8 C6 119.3(4) . . ?
C9 C8 H8 120.3(2) . . ?
C10 C9 C8 121.1(4) . . ?
C13 C9 C8 119.9(4) . . ?
C13 C9 C10 118.9(4) . . ?
H10 C10 C9 120.4(2) . . ?
C11 C10 C9 119.2(4) . . ?
C11 C10 H10 120.4(2) . . ?
C10 C11 C7 120.9(4) . . ?
C12 C11 C7 119.8(4) . . ?
C12 C11 C10 119.3(4) . . ?
O3 C12 C11 116.2(4) . . ?
O4 C12 C11 119.2(4) . . ?
O4 C12 O3 124.6(4) . . ?
O5 C13 C9 121.3(4) . . ?
O6 C13 C9 115.8(4) . . ?
O6 C13 O5 123.0(4) . . ?
C16 C14 C15 121.6(4) . . ?
O2 C14 C15 118.4(3) . . ?
O2 C14 C16 120.0(3) . . ?
H15 C15 C14 120.3(2) . . ?
C17 C15 C14 119.5(3) . . ?
C17 C15 H15 120.3(2) . . ?
H16 C16 C14 120.8(2) . . ?
C19 C16 C14 118.4(3) . . ?
C19 C16 H16 120.8(2) . . ?
C18 C17 C15 119.7(3) . . ?
C20 C17 C15 120.3(3) . . ?
C20 C17 C18 120.0(4) . . ?
H18 C18 C17 119.9(2) . . ?
C19 C18 C17 120.2(4) . . ?
C19 C18 H18 119.9(2) . . ?
C18 C19 C16 120.6(3) . . ?
C21 C19 C16 120.3(3) . . ?
C21 C19 C18 119.1(4) . . ?
O9 C20 C17 117.8(4) . . ?
O10 C20 C17 119.2(3) . . ?
O10 C20 O9 123.0(4) . . ?
O7 C21 C19 116.3(4) . . ?
O8 C21 C19 120.0(3) . . ?
O8 C21 O7 123.8(4) . . ?
C5 N1 C4 117.0(4) . . ?
C6 O1 C5 116.6(3) . . ?
C14 O2 C4 116.5(3) . . ?
H3a O3 C12 113(5) . . ?
H6 O6 C13 109.5 . . ?
H7a O7 C21 114(4) . . ?
H9 O9 C20 109(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C5 N1 -0.1(6) . . . . ?
C1 C2 C5 O1 179.0(4) . . . . ?
C1 C3 C4 N1 -2.1(5) . . . . ?
C1 C3 C4 O2 -179.7(4) . . . . ?
C2 C5 N1 C4 -0.9(5) . . . . ?
C2 C5 O1 C6 179.5(4) . . . . ?
C3 C4 N1 C5 2.1(5) . . . . ?
C3 C4 O2 C14 -176.1(4) . . . . ?
C4 N1 C5 O1 179.9(3) . . . . ?
C4 O2 C14 C15 106.4(3) . . . . ?
C4 O2 C14 C16 -75.0(3) . . . . ?
C5 O1 C6 C7 113.6(3) . . . . ?
C5 O1 C6 C8 -66.9(4) . . . . ?
C6 C7 C11 C10 -0.2(4) . . . . ?
C6 C7 C11 C12 178.3(3) . . . . ?
C6 C8 C9 C10 -0.5(4) . . . . ?
C6 C8 C9 C13 -178.9(3) . . . . ?
C7 C11 C10 C9 0.3(4) . . . . ?
C7 C11 C12 O3 4.7(4) . . . . ?
C7 C11 C12 O4 -175.2(4) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C8 C9 C13 O5 -173.8(4) . . . . ?
C8 C9 C13 O6 6.5(4) . . . . ?
C9 C10 C11 C12 -178.2(3) . . . . ?
C10 C11 C12 O3 -176.7(4) . . . . ?
C10 C11 C12 O4 3.4(4) . . . . ?
C14 C15 C17 C18 0.5(4) . . . . ?
C14 C15 C17 C20 -178.5(3) . . . . ?
C14 C16 C19 C18 1.7(4) . . . . ?
C14 C16 C19 C21 -177.1(3) . . . . ?
C15 C17 C18 C19 0.6(4) . . . . ?
C15 C17 C20 O9 -4.7(4) . . . . ?
C15 C17 C20 O10 175.8(4) . . . . ?
C16 C19 C18 C17 -1.7(4) . . . . ?
C16 C19 C21 O7 0.1(4) . . . . ?
C16 C19 C21 O8 179.3(4) . . . . ?
C17 C18 C19 C21 177.2(3) . . . . ?
C18 C19 C21 O7 -178.8(3) . . . . ?
C18 C19 C21 O8 0.4(4) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 176 electrons were 
found in a volume of 1104Å³ in 1 void per unit cell. 
This is consistent with the presence of 1[C2H3N] per Formula Unit 
which account for 176 electrons per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.300 0.242 0.250 275.7 44.2 '2 MeCN'
2 -0.046 0.258 0.750 275.7 44.2 '2 MeCN'
3 0.487 0.742 0.250 275.7 44.2 '2 MeCN'
4 0.019 0.758 0.750 275.7 44.2 '2 MeCN'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
O3 H3a 1 0.8200 0.0100 -0.0003

