# 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_tgh-m3h0-2
_database_code_depnum_ccdc_archive 'CCDC 2237582'
loop_
_audit_author_name
_audit_author_address
'Guo-Hong Tao'
;Sichuan University
China
;
_audit_update_record             
;
2023-05-21 deposited with the CCDC.	2023-05-26 downloaded from the CCDC.
;
_audit_creation_date             2023-05-19
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        '[MC1mim]2[Ho(NO3)5]'
_chemical_formula_moiety         'Ho N5 O15, 2(C6 H11 N2)'
_chemical_formula_sum            'C12 H22 Ho N9 O15'
_chemical_formula_weight         697.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H22HoN9O15
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ho Ho -14.9734 3.7046 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   15.4686(5)
_cell_length_b                   9.6881(3)
_cell_length_c                   16.6109(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.521(3)
_cell_angle_gamma                90
_cell_volume                     2488.45(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4123
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.6500
_cell_measurement_theta_min      3.8420
_shelx_estimated_absorpt_T_max   0.156
_shelx_estimated_absorpt_T_min   0.066
_exptl_absorpt_coefficient_mu    6.737
_exptl_absorpt_correction_T_max  0.226
_exptl_absorpt_correction_T_min  0.049
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.861
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 2 0.2294
0 -1 -2 0.2672
-2 0 -1 0.2560
9 -1 4 0.2802
0 6 0 0.2153
0 -6 0 0.2273
0 -4 8 0.2087
0 4 -8 0.2669
0 0 -11 0.2284
0 0 11 0.2935

_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.88
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.44
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0021 1.0013 2.0058 0.1686 -0.1657 -0.0642
0.0021 -1.0013 -2.0058 -0.1686 0.1657 0.0642
-2.0036 0.0003 -1.0030 -0.0230 0.0011 0.2213
8.9736 -0.7815 4.3923 -0.0207 0.0022 -0.9998
-0.1158 6.2848 0.3799 0.9948 -0.0255 0.0988
0.1231 -6.2848 -0.3763 -0.9947 0.0255 -0.0996
0.0329 -4.2619 7.9232 -0.6329 -0.6670 -0.3930
-0.0806 4.2565 -7.9301 0.6316 0.6656 0.3975
0.0269 -0.0988 -10.7742 -0.0708 0.8997 0.4307
-0.0323 0.0992 10.7743 0.0708 -0.8999 -0.4302

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7756
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.892
_diffrn_reflns_theta_min         5.328
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  75.00   1.00    1.00    --   36.29 -99.00  60.00   74
  2  ω    -31.00  53.00   1.00    1.00    --   36.29 -57.00-180.00   84
  3  ω     10.00 104.00   1.00    1.00    --   36.29  77.00-180.00   94
  4  ω     20.00 104.00   1.00    1.00    --   36.29  57.00  90.00   84
  5  ω     20.00 104.00   1.00    1.00    --   36.29  57.00 -30.00   84
  6  ω      1.00  75.00   1.00    1.00    --   36.29 -99.00 -90.00   74
  7  ω     38.00  91.00   1.00    1.00    --  108.00 -30.00 -90.00   53
  8  ω     90.00 175.00   1.00    1.00    --  108.00  61.00-120.00   85
  9  ω     38.00  91.00   1.00    1.00    --  108.00 -30.00 -60.00   53
 10  ω     38.00 116.00   1.00    1.00    --  108.00-111.00 150.00   78
 11  ω     39.00 109.00   1.00    1.00    --  108.00 -94.00-150.00   70
 12  ω     41.00 126.00   1.00    1.00    --  108.00 -61.00 120.00   85
 13  ω     40.00  98.00   1.00    1.00    --  108.00 -45.00 -30.00   58
 14  ω     40.00  98.00   1.00    1.00    --  108.00 -45.00-150.00   58
 15  ω     70.00 178.00   1.00    1.00    --  108.00  15.00 120.00  108
 16  ω    -31.00  53.00   1.00    1.00    --   36.29 -57.00 -60.00   84
 17  ω    -31.00  53.00   1.00    1.00    --   36.29 -57.00 120.00   84
 18  ω     10.00  74.00   1.00    1.00    --   36.29  77.00  30.00   64
 19  ω     20.00 104.00   1.00    1.00    --   36.29  57.00 -90.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0089488000
_diffrn_orient_matrix_UB_12      0.1581384000
_diffrn_orient_matrix_UB_13      0.0051419000
_diffrn_orient_matrix_UB_21      0.0412250000
_diffrn_orient_matrix_UB_22      0.0017490000
_diffrn_orient_matrix_UB_23      -0.0834192000
_diffrn_orient_matrix_UB_31      -0.0902264000
_diffrn_orient_matrix_UB_32      0.0164945000
_diffrn_orient_matrix_UB_33      -0.0403523000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2267
_reflns_number_total             2428
_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 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.909
_refine_diff_density_min         -0.894
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       0.00184(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2428
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.074
_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)+(0.0952P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1326
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_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
Ho1 Ho 0.750000 0.92993(3) 0.500000 0.0469(2) Uani 1 2 d S T P . .
O1 O 0.62964(19) 0.9845(4) 0.58385(19) 0.0682(8) Uani 1 1 d . . . . .
O2 O 0.60113(19) 0.8440(4) 0.4881(2) 0.0720(8) Uani 1 1 d . . . . .
O3 O 0.8403(3) 1.1416(7) 0.6973(2) 0.1082(16) Uani 1 1 d . . . . .
O4 O 0.8013(2) 1.1321(4) 0.57073(19) 0.0684(7) Uani 1 1 d . . . . .
O5 O 0.5038(2) 0.8898(5) 0.5755(3) 0.0961(13) Uani 1 1 d . . . . .
O6 O 0.7997(3) 0.9493(4) 0.6414(2) 0.0744(10) Uani 1 1 d . . . . .
O7 O 0.750000 0.5136(6) 0.500000 0.132(3) Uani 1 2 d S T P . .
O8 O 0.7587(2) 0.7054(3) 0.4363(2) 0.0735(8) Uani 1 1 d . . . . .
N1 N 0.5745(2) 0.9048(4) 0.5489(3) 0.0629(9) Uani 1 1 d . . . . .
N3 N 0.750000 0.6367(6) 0.500000 0.0778(16) Uani 1 2 d S T P . .
N4 N 0.8146(3) 1.0773(4) 0.6388(3) 0.0681(11) Uani 1 1 d . . . . .
N2 N 0.4151(3) 0.4726(7) 0.6645(3) 0.0880(14) Uani 1 1 d . . . . .
N5 N 0.5361(3) 0.4081(4) 0.6203(3) 0.0706(10) Uani 1 1 d . . . . .
C1 C 0.4722(4) 0.3685(6) 0.6643(3) 0.0753(13) Uani 1 1 d . . . . .
C2 C 0.6113(5) 0.3236(7) 0.6010(4) 0.1000(18) Uani 1 1 d . . . . .
H2A H 0.627087 0.267070 0.646540 0.150 Uiso 1 1 calc R U . . .
H2B H 0.658855 0.382624 0.588247 0.150 Uiso 1 1 calc R U . . .
H2C H 0.597216 0.265746 0.555618 0.150 Uiso 1 1 calc R U . . .
C3 C 0.3356(6) 0.4759(14) 0.7082(5) 0.142(4) Uani 1 1 d . . . . .
H3A H 0.288619 0.445630 0.673651 0.213 Uiso 1 1 calc R U . . .
H3B H 0.324744 0.568430 0.725987 0.213 Uiso 1 1 calc R U . . .
H3C H 0.340634 0.415823 0.754058 0.213 Uiso 1 1 calc R U . . .
C4 C 0.5211(5) 0.5387(6) 0.5927(3) 0.0808(15) Uani 1 1 d . . . . .
H4 H 0.557628 0.589312 0.560383 0.097 Uiso 1 1 calc R U . . .
C5 C 0.4644(6) 0.2358(8) 0.7066(4) 0.128(3) Uani 1 1 d . . . . .
H5A H 0.477323 0.161724 0.670472 0.191 Uiso 1 1 calc R U . . .
H5B H 0.406450 0.225357 0.725081 0.191 Uiso 1 1 calc R U . . .
H5C H 0.504255 0.233676 0.751867 0.191 Uiso 1 1 calc R U . . .
C6 C 0.4470(5) 0.5807(6) 0.6192(4) 0.0860(17) Uani 1 1 d . . . . .
H6 H 0.420906 0.665821 0.609711 0.103 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ho1 O1 2.413(3) 2_656 ?
Ho1 O1 2.413(3) . ?
Ho1 O2 2.452(3) . ?
Ho1 O2 2.452(3) 2_656 ?
Ho1 O4 2.408(3) . ?
Ho1 O4 2.408(3) 2_656 ?
Ho1 O6 2.459(4) 2_656 ?
Ho1 O6 2.459(4) . ?
Ho1 O8 2.424(3) . ?
Ho1 O8 2.424(3) 2_656 ?
O1 N1 1.279(6) . ?
O2 N1 1.248(5) . ?
O3 N4 1.213(6) . ?
O4 N4 1.261(6) . ?
O5 N1 1.200(5) . ?
O6 N4 1.262(5) . ?
O7 N3 1.193(10) 2_656 ?
O7 N3 1.193(10) . ?
O8 N3 1.261(5) 2_656 ?
O8 N3 1.261(5) . ?
N3 N3 0.000000(16) 2_656 ?
N2 C1 1.340(8) . ?
N2 C3 1.445(9) . ?
N2 C6 1.388(8) . ?
N5 C1 1.303(7) . ?
N5 C2 1.465(8) . ?
N5 C4 1.364(7) . ?
C1 C5 1.472(9) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C6 1.303(10) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6 0.9300 . ?

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 Ho1 O1 154.68(18) 2_656 . ?
O1 Ho1 O2 139.95(11) . 2_656 ?
O1 Ho1 O2 51.93(11) 2_656 2_656 ?
O1 Ho1 O2 51.93(11) . . ?
O1 Ho1 O2 139.95(11) 2_656 . ?
O1 Ho1 O6 70.04(12) 2_656 2_656 ?
O1 Ho1 O6 107.94(13) 2_656 . ?
O1 Ho1 O6 70.04(12) . . ?
O1 Ho1 O6 107.94(13) . 2_656 ?
O1 Ho1 O8 120.08(12) . . ?
O1 Ho1 O8 120.08(12) 2_656 2_656 ?
O1 Ho1 O8 83.80(12) 2_656 . ?
O1 Ho1 O8 83.80(12) . 2_656 ?
O2 Ho1 O2 140.29(17) . 2_656 ?
O2 Ho1 O6 71.33(12) . 2_656 ?
O2 Ho1 O6 71.33(12) 2_656 . ?
O2 Ho1 O6 111.84(13) 2_656 2_656 ?
O2 Ho1 O6 111.84(13) . . ?
O4 Ho1 O1 77.84(12) . . ?
O4 Ho1 O1 81.61(11) . 2_656 ?
O4 Ho1 O1 81.61(11) 2_656 . ?
O4 Ho1 O1 77.84(12) 2_656 2_656 ?
O4 Ho1 O2 86.59(12) . 2_656 ?
O4 Ho1 O2 86.59(12) 2_656 . ?
O4 Ho1 O2 127.74(11) 2_656 2_656 ?
O4 Ho1 O2 127.74(11) . . ?
O4 Ho1 O4 71.11(17) . 2_656 ?
O4 Ho1 O6 119.64(12) . 2_656 ?
O4 Ho1 O6 51.77(12) . . ?
O4 Ho1 O6 119.64(12) 2_656 . ?
O4 Ho1 O6 51.77(12) 2_656 2_656 ?
O4 Ho1 O8 122.57(12) 2_656 . ?
O4 Ho1 O8 157.16(14) 2_656 2_656 ?
O4 Ho1 O8 122.57(12) . 2_656 ?
O4 Ho1 O8 157.16(14) . . ?
O6 Ho1 O6 171.24(18) 2_656 . ?
O8 Ho1 O2 70.58(13) . 2_656 ?
O8 Ho1 O2 73.93(12) 2_656 2_656 ?
O8 Ho1 O2 70.58(13) 2_656 . ?
O8 Ho1 O2 73.93(12) . . ?
O8 Ho1 O6 117.77(13) . . ?
O8 Ho1 O6 117.77(13) 2_656 2_656 ?
O8 Ho1 O6 70.80(13) . 2_656 ?
O8 Ho1 O6 70.80(13) 2_656 . ?
O8 Ho1 O8 52.41(17) . 2_656 ?
N1 O1 Ho1 96.9(3) . . ?
N1 O2 Ho1 96.0(2) . . ?
N4 O4 Ho1 98.0(3) . . ?
N4 O6 Ho1 95.4(3) . . ?
N3 O7 N3 0.000(2) 2_656 . ?
N3 O8 Ho1 95.7(3) . . ?
N3 O8 Ho1 95.7(3) 2_656 . ?
N3 O8 N3 0.0(5) 2_656 . ?
O2 N1 O1 115.0(3) . . ?
O5 N1 O1 120.6(5) . . ?
O5 N1 O2 124.4(5) . . ?
O7 N3 O8 121.9(3) . 2_656 ?
O7 N3 O8 121.9(3) . . ?
O8 N3 O8 116.2(6) 2_656 . ?
N3 N3 O7 0(10) 2_656 . ?
N3 N3 O8 0(10) 2_656 . ?
N3 N3 O8 0(10) 2_656 2_656 ?
O3 N4 O4 123.0(5) . . ?
O3 N4 O6 122.2(5) . . ?
O4 N4 O6 114.8(4) . . ?
C1 N2 C3 125.9(8) . . ?
C1 N2 C6 108.8(5) . . ?
C6 N2 C3 125.2(8) . . ?
C1 N5 C2 125.3(5) . . ?
C1 N5 C4 109.6(5) . . ?
C4 N5 C2 125.0(5) . . ?
N2 C1 C5 126.4(6) . . ?
N5 C1 N2 106.9(5) . . ?
N5 C1 C5 126.7(7) . . ?
N5 C2 H2A 109.5 . . ?
N5 C2 H2B 109.5 . . ?
N5 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N5 C4 H4 125.7 . . ?
C6 C4 N5 108.7(6) . . ?
C6 C4 H4 125.7 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6 127.0 . . ?
C4 C6 N2 106.0(5) . . ?
C4 C6 H6 127.0 . . ?

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
Ho1 O1 N1 O2 -4.2(4) . . . . ?
Ho1 O1 N1 O5 174.1(4) . . . . ?
Ho1 O2 N1 O1 4.1(4) . . . . ?
Ho1 O2 N1 O5 -174.1(4) . . . . ?
Ho1 O4 N4 O3 -178.4(4) . . . . ?
Ho1 O4 N4 O6 2.0(4) . . . . ?
Ho1 O6 N4 O3 178.5(4) . . . . ?
Ho1 O6 N4 O4 -2.0(4) . . . . ?
Ho1 O8 N3 O7 180.000(3) . . . . ?
Ho1 O8 N3 O8 -0.002(2) . . . 2_656 ?
Ho1 O8 N3 N3 0.0(9) . . . 2_656 ?
N3 O7 N3 O8 0(100) 2_656 . . . ?
N3 O7 N3 O8 0(100) 2_656 . . 2_656 ?
N3 O8 N3 O7 0(100) 2_656 . . . ?
N3 O8 N3 O8 0(100) 2_656 . . 2_656 ?
N5 C4 C6 N2 -0.1(7) . . . . ?
C1 N2 C6 C4 0.6(7) . . . . ?
C1 N5 C4 C6 -0.4(7) . . . . ?
C2 N5 C1 N2 -177.3(5) . . . . ?
C2 N5 C1 C5 3.4(9) . . . . ?
C2 N5 C4 C6 177.6(6) . . . . ?
C3 N2 C1 N5 -177.5(6) . . . . ?
C3 N2 C1 C5 1.8(9) . . . . ?
C3 N2 C6 C4 177.3(6) . . . . ?
C4 N5 C1 N2 0.8(6) . . . . ?
C4 N5 C1 C5 -178.5(6) . . . . ?
C6 N2 C1 N5 -0.9(6) . . . . ?
C6 N2 C1 C5 178.5(6) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.693
_oxdiff_exptl_absorpt_empirical_full_min 0.690
####################################################################### 
# 
# 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_tgh-m3er-2-rt
_database_code_depnum_ccdc_archive 'CCDC 2237584'
loop_
_audit_author_name
_audit_author_address
'Guo-Hong Tao'
;Sichuan University
China
;
_audit_update_record             
;
2023-05-21 deposited with the CCDC.	2023-05-26 downloaded from the CCDC.
;
_audit_creation_date             2023-05-19
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        '[MC1mim]2[Er(NO3)5]'
_chemical_formula_moiety         'Er N5 O15, 2(C6 H11 N2)'
_chemical_formula_sum            'C12 H22 Er N9 O15'
_chemical_formula_weight         699.64
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H11Er0.5N4.5O7.5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Er Er -9.4367 3.9380 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.6110(2)
_cell_length_b                   9.6805(2)
_cell_length_c                   15.5021(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.496(2)
_cell_angle_gamma                90
_cell_volume                     2491.93(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8544
_cell_measurement_temperature    276(2)
_cell_measurement_theta_max      72.6380
_cell_measurement_theta_min      3.8660
_shelx_estimated_absorpt_T_max   0.418
_shelx_estimated_absorpt_T_min   0.192
_exptl_absorpt_coefficient_mu    7.048
_exptl_absorpt_correction_T_max  0.440
_exptl_absorpt_correction_T_min  0.206
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.865
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1380
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 4 7 0.1268
-4 -4 -7 0.1420
2 6 -3 0.1247
7 -3 -6 0.0942
0 4 8 0.1354
0 5 -5 0.1312
0 6 0 0.0875
-11 0 0 0.0870
11 0 0 0.0650
0 -4 8 0.1671

_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.0094 4.0006 6.9959 -0.9502 -0.3111 -0.2055
-4.0094 -4.0006 -6.9959 0.9502 0.3111 0.2055
2.0071 6.0054 -3.0020 -0.6208 -0.1409 0.7925
6.9865 -3.0040 -6.0019 0.6813 -0.6932 0.2008
0.0125 4.0019 7.9978 -0.9778 0.0618 -0.2810
0.0052 5.0057 -5.0004 -0.3615 0.0285 0.8655
0.0104 6.0055 -0.0014 -0.7781 0.0537 0.5519
-10.9935 0.0040 0.0056 0.0818 1.0165 0.0156
10.9935 -0.0040 -0.0056 -0.0818 -1.0165 -0.0156
-0.0014 -4.0055 7.9997 0.0597 -0.0098 -1.0169

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12039
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.721
_diffrn_reflns_theta_min         5.289
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      276(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     31.00  97.00   1.00    1.00    --   36.54-137.00  53.00   66
  2  ω    -31.00  53.00   1.00    1.00    --   36.54 -57.00  30.00   84
  3  ω    -33.00  55.00   1.00    1.00    --   36.54 -38.00-180.00   88
  4  ω     23.00  90.00   1.00    1.00    --   36.54-125.00 -90.00   67
  5  ω    -33.00  55.00   1.00    1.00    --   36.54 -38.00  60.00   88
  6  ω    -31.00  63.00   1.00    1.00    --   36.54 -77.00 -90.00   94
  7  ω     87.00 178.00   1.00    1.73    --  108.00  30.00-150.00   91
  8  ω     38.00  91.00   1.00    1.73    --  108.00 -30.00 -60.00   53
  9  ω     38.00  91.00   1.00    1.73    --  108.00 -30.00   0.00   53
 10  ω     38.00  91.00   1.00    1.73    --  108.00 -30.00  90.00   53
 11  ω    100.00 178.00   1.00    1.73    --  108.00 111.00  30.00   78
 12  ω    100.00 178.00   1.00    1.73    --  108.00 111.00 120.00   78
 13  ω     41.00 126.00   1.00    1.73    --  108.00 -61.00 -60.00   85
 14  ω     40.00  98.00   1.00    1.73    --  108.00 -45.00-120.00   58
 15  ω     57.00 150.00   1.00    1.73    --  108.00 178.00 -30.00   93
 16  ω     10.00 104.00   1.00    1.00    --   36.54  77.00-120.00   94
 17  ω     20.00 104.00   1.00    1.00    --   36.54  57.00  90.00   84
 18  ω     20.00 104.00   1.00    1.00    --   36.54  57.00-180.00   84
 19  ω     10.00 104.00   1.00    1.00    --   36.54  77.00 -30.00   94
 20  ω     70.00 178.00   1.00    1.73    --  108.00  15.00  90.00  108
 21  ω     70.00 178.00   1.00    1.73    --  108.00  15.00   0.00  108
 22  ω     91.00 176.00   1.00    1.73    --  108.00  45.00 -90.00   85
 23  ω     87.00 178.00   1.00    1.73    --  108.00  30.00 150.00   91
 24  ω     41.00 126.00   1.00    1.73    --  108.00 -61.00  90.00   85
 25  ω     38.00  67.00   1.00    1.73    --  108.00-111.00 -30.00   29
 26  ω     39.00 109.00   1.00    1.73    --  108.00 -94.00  90.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0075203000
_diffrn_orient_matrix_UB_12      -0.1295665000
_diffrn_orient_matrix_UB_13      -0.0574187000
_diffrn_orient_matrix_UB_21      -0.0924622000
_diffrn_orient_matrix_UB_22      0.0091030000
_diffrn_orient_matrix_UB_23      0.0033163000
_diffrn_orient_matrix_UB_31      -0.0014271000
_diffrn_orient_matrix_UB_32      0.0918882000
_diffrn_orient_matrix_UB_33      -0.0811094000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2342
_reflns_number_total             2462
_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 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.869
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       0.00292(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2462
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0696P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.0971
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_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
Er01 Er 0.250000 0.32078(2) 0.500000 0.04479(17) Uani 1 2 d S T P . .
O1 O 0.17947(18) 0.1186(3) 0.4487(2) 0.0673(7) Uani 1 1 d . . . . .
O2 O 0.23710(19) 0.4061(4) 0.35180(19) 0.0702(7) Uani 1 1 d . . . . .
O3 O 0.0536(2) 0.1095(6) 0.4099(3) 0.1059(15) Uani 1 1 d . . . . .
O4 O 0.33294(18) 0.2666(4) 0.38042(18) 0.0656(7) Uani 1 1 d . . . . .
O5 O 0.3239(3) 0.3606(5) 0.2539(2) 0.0918(12) Uani 1 1 d . . . . .
O6 O 0.3136(2) 0.5437(3) 0.4907(2) 0.0713(7) Uani 1 1 d . . . . .
O7 O 0.250000 0.7372(6) 0.500000 0.127(3) Uani 1 2 d S T P . .
O8 O 0.1091(2) 0.3019(4) 0.4512(2) 0.0714(8) Uani 1 1 d . . . . .
N1 N 0.250000 0.6133(6) 0.500000 0.0772(15) Uani 1 2 d S T P . .
N3 N 0.1115(3) 0.1743(4) 0.4353(3) 0.0672(10) Uani 1 1 d . . . . .
N4 N 0.2987(2) 0.3449(4) 0.3251(2) 0.0601(8) Uani 1 1 d . . . . .
N2 N 0.4145(2) 0.7757(6) 0.1651(3) 0.0875(13) Uani 1 1 d . . . . .
N5 N 0.3706(3) 0.8417(4) 0.2861(3) 0.0695(10) Uani 1 1 d . . . . .
C1 C 0.4144(3) 0.8813(6) 0.2216(4) 0.0766(13) Uani 1 1 d . . . . .
C2 C 0.4563(4) 1.0163(8) 0.2150(6) 0.130(3) Uani 1 1 d . . . . .
H2A H 0.421352 1.088645 0.233959 0.195 Uiso 1 1 calc R U . . .
H2B H 0.470101 1.032537 0.156125 0.195 Uiso 1 1 calc R U . . .
H2C H 0.504379 1.015091 0.250677 0.195 Uiso 1 1 calc R U . . .
C3 C 0.3519(4) 0.9262(7) 0.3623(4) 0.0971(17) Uani 1 1 d . . . . .
H3A H 0.400306 0.968756 0.384571 0.146 Uiso 1 1 calc R U . . .
H3B H 0.329470 0.868381 0.405837 0.146 Uiso 1 1 calc R U . . .
H3C H 0.313666 0.996502 0.345906 0.146 Uiso 1 1 calc R U . . .
C4 C 0.3423(3) 0.7115(6) 0.2710(4) 0.0800(14) Uani 1 1 d . . . . .
H4 H 0.309409 0.660869 0.306957 0.096 Uiso 1 1 calc R U . . .
C5 C 0.4591(4) 0.7740(13) 0.0853(5) 0.140(4) Uani 1 1 d . . . . .
H5A H 0.457644 0.864292 0.059672 0.210 Uiso 1 1 calc R U . . .
H5B H 0.434978 0.708479 0.046004 0.210 Uiso 1 1 calc R U . . .
H5C H 0.513955 0.748203 0.097757 0.210 Uiso 1 1 calc R U . . .
C6 C 0.3697(3) 0.6705(5) 0.1968(5) 0.0826(15) Uani 1 1 d . . . . .
H6 H 0.360230 0.585392 0.170625 0.099 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Er01 O1 2.406(3) 2_556 ?
Er01 O1 2.406(3) . ?
Er01 O2 2.445(3) 2_556 ?
Er01 O2 2.445(3) . ?
Er01 O4 2.396(3) . ?
Er01 O4 2.396(3) 2_556 ?
Er01 O6 2.409(3) 2_556 ?
Er01 O6 2.409(3) . ?
Er01 O8 2.447(3) . ?
Er01 O8 2.447(3) 2_556 ?
O1 N3 1.264(5) . ?
O2 N4 1.261(5) . ?
O3 N3 1.206(5) . ?
O4 N4 1.268(5) . ?
O5 N4 1.201(5) . ?
O6 N1 1.265(5) 2_556 ?
O6 N1 1.265(5) . ?
O7 N1 1.200(10) 2_556 ?
O7 N1 1.200(10) . ?
O8 N3 1.260(5) . ?
N1 N1 0.000(12) 2_556 ?
N2 C1 1.346(8) . ?
N2 C5 1.457(8) . ?
N2 C6 1.361(8) . ?
N5 C1 1.309(7) . ?
N5 C3 1.476(7) . ?
N5 C4 1.364(7) . ?
C1 C2 1.485(8) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C6 1.310(9) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6 0.9300 . ?

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 Er01 O1 71.11(16) 2_556 . ?
O1 Er01 O2 86.21(11) 2_556 2_556 ?
O1 Er01 O2 127.98(11) . 2_556 ?
O1 Er01 O2 86.21(11) . . ?
O1 Er01 O2 127.98(11) 2_556 . ?
O1 Er01 O6 156.87(13) 2_556 2_556 ?
O1 Er01 O6 122.55(12) . 2_556 ?
O1 Er01 O6 156.87(13) . . ?
O1 Er01 O6 122.55(12) 2_556 . ?
O1 Er01 O8 119.66(11) 2_556 . ?
O1 Er01 O8 119.66(11) . 2_556 ?
O1 Er01 O8 51.94(11) 2_556 2_556 ?
O1 Er01 O8 51.94(11) . . ?
O2 Er01 O2 140.54(16) . 2_556 ?
O2 Er01 O8 112.05(12) 2_556 . ?
O2 Er01 O8 71.04(12) 2_556 2_556 ?
O2 Er01 O8 112.05(12) . 2_556 ?
O2 Er01 O8 71.04(12) . . ?
O4 Er01 O1 78.05(11) . 2_556 ?
O4 Er01 O1 78.05(11) 2_556 . ?
O4 Er01 O1 81.42(11) . . ?
O4 Er01 O1 81.42(11) 2_556 2_556 ?
O4 Er01 O2 139.69(11) . 2_556 ?
O4 Er01 O2 52.07(11) 2_556 2_556 ?
O4 Er01 O2 52.07(11) . . ?
O4 Er01 O2 139.69(11) 2_556 . ?
O4 Er01 O4 154.70(17) . 2_556 ?
O4 Er01 O6 83.56(11) 2_556 2_556 ?
O4 Er01 O6 120.30(11) . 2_556 ?
O4 Er01 O6 83.56(11) . . ?
O4 Er01 O6 120.30(11) 2_556 . ?
O4 Er01 O8 107.98(12) . . ?
O4 Er01 O8 107.98(12) 2_556 2_556 ?
O4 Er01 O8 70.03(12) 2_556 . ?
O4 Er01 O8 70.03(12) . 2_556 ?
O6 Er01 O2 74.10(11) 2_556 . ?
O6 Er01 O2 70.68(12) 2_556 2_556 ?
O6 Er01 O2 74.10(11) . 2_556 ?
O6 Er01 O2 70.67(12) . . ?
O6 Er01 O6 52.76(16) . 2_556 ?
O6 Er01 O8 117.77(12) . . ?
O6 Er01 O8 70.61(12) 2_556 . ?
O6 Er01 O8 117.77(12) 2_556 2_556 ?
O6 Er01 O8 70.61(12) . 2_556 ?
O8 Er01 O8 171.42(17) . 2_556 ?
N3 O1 Er01 97.6(2) . . ?
N4 O2 Er01 95.6(2) . . ?
N4 O4 Er01 97.8(2) . . ?
N1 O6 Er01 95.8(3) 2_556 . ?
N1 O6 Er01 95.8(3) . . ?
N1 O6 N1 0.000(1) 2_556 . ?
N1 O7 N1 0.000(1) 2_556 . ?
N3 O8 Er01 95.7(3) . . ?
O6 N1 O6 115.6(5) 2_556 . ?
O7 N1 O6 122.2(3) . 2_556 ?
O7 N1 O6 122.2(3) . . ?
N1 N1 O6 0(10) 2_556 2_556 ?
N1 N1 O6 0(10) 2_556 . ?
N1 N1 O7 0(10) 2_556 . ?
O3 N3 O1 122.3(5) . . ?
O3 N3 O8 123.0(5) . . ?
O8 N3 O1 114.7(4) . . ?
O2 N4 O4 114.4(3) . . ?
O5 N4 O2 123.2(4) . . ?
O5 N4 O4 122.4(4) . . ?
C1 N2 C5 124.8(7) . . ?
C1 N2 C6 108.8(5) . . ?
C6 N2 C5 126.4(8) . . ?
C1 N5 C3 125.6(5) . . ?
C1 N5 C4 109.6(5) . . ?
C4 N5 C3 124.8(5) . . ?
N2 C1 C2 127.9(6) . . ?
N5 C1 N2 106.6(5) . . ?
N5 C1 C2 125.5(7) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N5 C3 H3A 109.5 . . ?
N5 C3 H3B 109.5 . . ?
N5 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N5 C4 H4 126.1 . . ?
C6 C4 N5 107.7(5) . . ?
C6 C4 H4 126.1 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6 126.4 . . ?
C4 C6 N2 107.3(5) . . ?
C4 C6 H6 126.4 . . ?

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
Er01 O1 N3 O3 -178.3(4) . . . . ?
Er01 O1 N3 O8 1.3(4) . . . . ?
Er01 O2 N4 O4 4.3(3) . . . . ?
Er01 O2 N4 O5 -174.6(4) . . . . ?
Er01 O4 N4 O2 -4.4(4) . . . . ?
Er01 O4 N4 O5 174.5(4) . . . . ?
Er01 O6 N1 O6 -0.002(0) . . . 2_556 ?
Er01 O6 N1 O7 180.000(0) . . . . ?
Er01 O6 N1 N1 0(100) . . . 2_556 ?
Er01 O8 N3 O1 -1.3(4) . . . . ?
Er01 O8 N3 O3 178.3(4) . . . . ?
N1 O6 N1 O6 0(100) 2_556 . . 2_556 ?
N1 O6 N1 O7 0(100) 2_556 . . . ?
N1 O7 N1 O6 0(100) 2_556 . . . ?
N1 O7 N1 O6 0(28) 2_556 . . 2_556 ?
N5 C4 C6 N2 -0.6(6) . . . . ?
C1 N2 C6 C4 0.4(6) . . . . ?
C1 N5 C4 C6 0.6(6) . . . . ?
C3 N5 C1 N2 -178.1(5) . . . . ?
C3 N5 C1 C2 2.8(8) . . . . ?
C3 N5 C4 C6 178.4(5) . . . . ?
C4 N5 C1 N2 -0.3(5) . . . . ?
C4 N5 C1 C2 -179.3(5) . . . . ?
C5 N2 C1 N5 -177.3(5) . . . . ?
C5 N2 C1 C2 1.7(8) . . . . ?
C5 N2 C6 C4 177.6(5) . . . . ?
C6 N2 C1 N5 -0.1(5) . . . . ?
C6 N2 C1 C2 178.9(5) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.329
_oxdiff_exptl_absorpt_empirical_full_min 0.763
####################################################################### 
# 
# 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_tgh-m3lun5-2
_database_code_depnum_ccdc_archive 'CCDC 2237590'
loop_
_audit_author_name
_audit_author_address
'Guo-Hong Tao'
;Sichuan University
China
;
_audit_update_record             
;
2023-05-21 deposited with the CCDC.	2023-05-26 downloaded from the CCDC.
;
_audit_creation_date             2023-05-19
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        '[MC1mim]2[Lu(NO3)5]'
_chemical_formula_moiety         'Lu N5 O15, 2(C6 H11 N2)'
_chemical_formula_sum            'C12 H22 Lu N9 O15'
_chemical_formula_weight         707.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H11Lu0.5N4.5O7.5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Lu Lu -6.6179 4.6937 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   15.5030(6)
_cell_length_b                   9.6407(5)
_cell_length_c                   16.5976(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.417(4)
_cell_angle_gamma                90
_cell_volume                     2479.92(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4201
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9960
_cell_measurement_theta_min      3.9850
_shelx_estimated_absorpt_T_max   0.147
_shelx_estimated_absorpt_T_min   0.051
_exptl_absorpt_coefficient_mu    8.421
_exptl_absorpt_correction_T_max  0.243
_exptl_absorpt_correction_T_min  0.019
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.895
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -1 11 0.2043
4 -5 3 0.4056
6 1 -9 0.2184
-7 0 8 0.2911
-1 0 11 0.1425
4 -5 -2 0.4614
2 -6 0 0.4588
1 0 11 0.1636
-1 -1 -11 0.1793
8 0 6 0.2960
-8 -2 -5 0.3782
10 -1 2 0.3667
-10 -1 2 0.3843
7 1 -8 0.2043
7 -4 4 0.4193
1 -4 8 0.2400
1 1 11 0.2812
-8 0 7 0.3175
-2 4 -8 0.3697

_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.88
_exptl_crystal_size_mid          0.79
_exptl_crystal_size_min          0.37
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.9954 -0.9953 11.0054 0.6681 -0.1530 0.7930
3.9909 -5.0033 2.9856 -0.4286 0.1527 0.8201
6.0006 0.9932 -9.0076 -0.8419 -0.1818 -0.5603
-6.9993 0.0074 8.0104 0.9202 0.1786 0.3645
-0.9916 0.0043 11.0071 0.6596 -0.3235 0.7136
3.9866 -5.0049 -2.0173 -0.6965 0.3297 0.4846
1.9836 -6.0032 -0.0170 -0.5105 0.4955 0.6736
1.0102 0.0029 11.0055 0.5191 -0.4555 0.7629
-1.0132 -1.0032 -11.0080 -0.5808 0.5601 -0.6588
8.0120 -0.0035 5.9968 -0.2404 -0.7404 0.5997
-8.0172 -1.9967 -5.0013 0.1707 0.9141 -0.3244
10.0073 -1.0065 1.9902 -0.6569 -0.6261 0.4845
-10.0100 -0.9928 2.0069 0.7478 0.6936 -0.0080
7.0023 0.9929 -8.0079 -0.8586 -0.2832 -0.4686
6.9973 -4.0047 3.9862 -0.5241 -0.1853 0.8571
0.9955 -3.9993 7.9935 0.1117 0.0690 0.9778
1.0132 1.0032 11.0080 0.5808 -0.5601 0.6588
-8.0010 0.0078 7.0107 0.9369 0.2800 0.2728
-1.9964 4.0000 -7.9927 -0.0414 -0.0030 -1.0024

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1188
_diffrn_reflns_av_unetI/netI     0.0865
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6677
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         5.306
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     23.00  89.00   1.00    1.00    --   36.04-125.00 120.00   66
  2  ω     17.00 105.00   1.00    1.00    --   36.04  38.00 -90.00   88
  3  ω     23.00  89.00   1.00    1.00    --   36.04-125.00 -30.00   66
  4  ω    -33.00  55.00   1.00    1.00    --   36.04 -38.00 -30.00   88
  5  ω     23.00  89.00   1.00    1.00    --   36.04-125.00   0.00   66
  6  ω     17.00 105.00   1.00    1.00    --   36.04  38.00 120.00   88
  7  ω     40.00  98.00   1.00    1.49    --  108.00 -45.00-150.00   58
  8  ω     91.00 176.00   1.00    1.49    --  108.00  45.00 -30.00   85
  9  ω     38.00  91.00   1.00    1.49    --  108.00 -30.00 150.00   53
 10  ω     40.00  98.00   1.00    1.49    --  108.00 -45.00 -90.00   58
 11  ω     39.00 177.00   1.00    1.49    --  108.00   0.00 -60.00  138
 12  ω     38.00  91.00   1.00    1.49    --  108.00 -30.00  90.00   53
 13  ω     40.00  98.00   1.00    1.49    --  108.00 -45.00-120.00   58
 14  ω     38.00  91.00   1.00    1.49    --  108.00 -30.00  30.00   53
 15  ω     38.00  91.00   1.00    1.49    --  108.00 -30.00 -90.00   53
 16  ω     40.00  98.00   1.00    1.49    --  108.00 -45.00  90.00   58
 17  ω      9.00 102.00   1.00    1.00    --   36.04  77.00 150.00   93
 18  ω     19.00 103.00   1.00    1.00    --   36.04  57.00   0.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0700881000
_diffrn_orient_matrix_UB_12      0.0617342000
_diffrn_orient_matrix_UB_13      0.0535833000
_diffrn_orient_matrix_UB_21      -0.0660309000
_diffrn_orient_matrix_UB_22      -0.1042530000
_diffrn_orient_matrix_UB_23      -0.0353014000
_diffrn_orient_matrix_UB_31      0.0245881000
_diffrn_orient_matrix_UB_32      -0.1042732000
_diffrn_orient_matrix_UB_33      0.0670863000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2125
_reflns_number_total             2218
_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 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.926
_refine_diff_density_min         -1.402
_refine_diff_density_rms         0.195
_refine_ls_extinction_coef       0.0032(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0629
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1097P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1473
_refine_ls_wR_factor_ref         0.1493
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_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
Lu1 Lu 0.750000 0.07226(4) 0.500000 0.0415(3) Uani 1 2 d S T P . .
O1 O 0.6981(4) -0.1276(6) 0.4313(3) 0.0637(12) Uani 1 1 d . . . . .
O2 O 0.6026(4) 0.1569(6) 0.4856(3) 0.0668(13) Uani 1 1 d . . . . .
O3 O 0.6589(6) -0.1384(12) 0.3048(4) 0.106(3) Uani 1 1 d . . . . .
O4 O 0.6331(3) 0.0167(6) 0.5820(3) 0.0628(12) Uani 1 1 d . . . . .
O5 O 0.5053(5) 0.1108(9) 0.5737(5) 0.090(2) Uani 1 1 d . . . . .
O6 O 0.7033(5) 0.0550(6) 0.3597(4) 0.0693(17) Uani 1 1 d . . . . .
O7 O 0.750000 0.4883(11) 0.500000 0.124(5) Uani 1 2 d S T P . .
O8 O 0.7406(4) 0.2934(5) 0.5637(4) 0.0697(14) Uani 1 1 d . . . . .
N1 N 0.750000 0.3626(11) 0.500000 0.069(3) Uani 1 2 d S T P . .
N3 N 0.6857(5) -0.0743(7) 0.3638(5) 0.065(2) Uani 1 1 d . . . . .
N5 N 0.5760(4) 0.0946(6) 0.5480(4) 0.0568(15) Uani 1 1 d . . . . .
N2 N 0.4140(6) 0.5264(12) 0.6647(4) 0.089(3) Uani 1 1 d . . . . .
N4 N 0.5364(7) 0.5928(7) 0.6214(5) 0.0686(19) Uani 1 1 d . . . . .
C1 C 0.4717(7) 0.6333(11) 0.6651(4) 0.077(3) Uani 1 1 d . . . . .
C2 C 0.6126(9) 0.6754(12) 0.6032(7) 0.094(3) Uani 1 1 d . . . . .
H2A H 0.595005 0.760026 0.577140 0.141 Uiso 1 1 calc R U . . .
H2B H 0.649113 0.623753 0.568235 0.141 Uiso 1 1 calc R U . . .
H2C H 0.643769 0.696675 0.652386 0.141 Uiso 1 1 calc R U . . .
C3 C 0.4647(11) 0.7678(14) 0.7069(7) 0.129(6) Uani 1 1 d . . . . .
H3A H 0.506722 0.772001 0.750309 0.194 Uiso 1 1 calc R U . . .
H3B H 0.407912 0.777101 0.728042 0.194 Uiso 1 1 calc R U . . .
H3C H 0.474898 0.841651 0.669565 0.194 Uiso 1 1 calc R U . . .
C4 C 0.5218(8) 0.4613(10) 0.5927(6) 0.078(3) Uani 1 1 d . . . . .
H4 H 0.558516 0.410592 0.560380 0.094 Uiso 1 1 calc R U . . .
C5 C 0.3351(10) 0.524(2) 0.7093(8) 0.134(6) Uani 1 1 d . . . . .
H5A H 0.339208 0.589239 0.752864 0.201 Uiso 1 1 calc R U . . .
H5B H 0.326222 0.432519 0.730484 0.201 Uiso 1 1 calc R U . . .
H5C H 0.287399 0.548365 0.674098 0.201 Uiso 1 1 calc R U . . .
C6 C 0.4460(10) 0.4192(9) 0.6191(7) 0.080(3) Uani 1 1 d . . . . .
H6 H 0.419639 0.334151 0.608911 0.096 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Lu1 O1 2.369(5) . ?
Lu1 O1 2.369(5) 2_656 ?
Lu1 O2 2.433(6) 2_656 ?
Lu1 O2 2.433(6) . ?
Lu1 O4 2.356(5) 2_656 ?
Lu1 O4 2.355(5) . ?
Lu1 O6 2.427(6) . ?
Lu1 O6 2.427(6) 2_656 ?
Lu1 O8 2.386(5) 2_656 ?
Lu1 O8 2.386(5) . ?
O1 N3 1.244(10) . ?
O2 N5 1.275(9) . ?
O3 N3 1.221(10) . ?
O4 N5 1.280(10) . ?
O5 N5 1.196(10) . ?
O6 N3 1.279(8) . ?
O7 O7 0.00(2) 2_656 ?
O7 N1 1.212(19) . ?
O7 N1 1.212(19) 2_656 ?
O8 N1 1.261(8) 2_656 ?
O8 N1 1.261(8) . ?
N1 N1 0.00(2) 2_656 ?
N2 C1 1.365(16) . ?
N2 C5 1.446(17) . ?
N2 C6 1.380(14) . ?
N4 C1 1.312(14) . ?
N4 C2 1.462(15) . ?
N4 C4 1.371(12) . ?
C1 C3 1.476(14) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C6 1.328(18) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6 0.9300 . ?

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 Lu1 O1 71.2(3) . 2_656 ?
O1 Lu1 O2 128.83(19) . 2_656 ?
O1 Lu1 O2 128.83(19) 2_656 . ?
O1 Lu1 O2 85.3(2) . . ?
O1 Lu1 O2 85.3(2) 2_656 2_656 ?
O1 Lu1 O6 119.7(2) 2_656 . ?
O1 Lu1 O6 52.6(2) . . ?
O1 Lu1 O6 119.7(2) . 2_656 ?
O1 Lu1 O6 52.6(2) 2_656 2_656 ?
O1 Lu1 O8 122.5(2) 2_656 . ?
O1 Lu1 O8 156.4(2) 2_656 2_656 ?
O1 Lu1 O8 122.5(2) . 2_656 ?
O1 Lu1 O8 156.4(2) . . ?
O2 Lu1 O2 140.8(3) . 2_656 ?
O4 Lu1 O1 80.6(2) 2_656 2_656 ?
O4 Lu1 O1 78.1(2) 2_656 . ?
O4 Lu1 O1 78.1(2) . 2_656 ?
O4 Lu1 O1 80.6(2) . . ?
O4 Lu1 O2 138.95(19) . 2_656 ?
O4 Lu1 O2 53.02(19) . . ?
O4 Lu1 O2 53.02(19) 2_656 2_656 ?
O4 Lu1 O2 138.95(19) 2_656 . ?
O4 Lu1 O4 153.7(3) . 2_656 ?
O4 Lu1 O6 108.9(2) . . ?
O4 Lu1 O6 108.9(2) 2_656 2_656 ?
O4 Lu1 O6 69.2(2) . 2_656 ?
O4 Lu1 O6 69.2(2) 2_656 . ?
O4 Lu1 O8 121.0(2) . 2_656 ?
O4 Lu1 O8 121.0(2) 2_656 . ?
O4 Lu1 O8 83.8(2) . . ?
O4 Lu1 O8 83.8(2) 2_656 2_656 ?
O6 Lu1 O2 70.8(2) . . ?
O6 Lu1 O2 70.8(2) 2_656 2_656 ?
O6 Lu1 O2 112.0(2) 2_656 . ?
O6 Lu1 O2 112.0(2) . 2_656 ?
O6 Lu1 O6 172.1(3) . 2_656 ?
O8 Lu1 O2 74.0(2) 2_656 . ?
O8 Lu1 O2 71.1(2) . . ?
O8 Lu1 O2 71.1(2) 2_656 2_656 ?
O8 Lu1 O2 74.0(2) . 2_656 ?
O8 Lu1 O6 69.9(2) 2_656 . ?
O8 Lu1 O6 117.8(2) 2_656 2_656 ?
O8 Lu1 O6 69.9(2) . 2_656 ?
O8 Lu1 O6 117.8(2) . . ?
O8 Lu1 O8 53.3(3) 2_656 . ?
N3 O1 Lu1 98.1(4) . . ?
N5 O2 Lu1 94.8(4) . . ?
N5 O4 Lu1 98.4(4) . . ?
N3 O6 Lu1 94.3(5) . . ?
O7 O7 N1 0(10) 2_656 2_656 ?
O7 O7 N1 0(10) 2_656 . ?
N1 O7 N1 0.000(2) . 2_656 ?
N1 O8 Lu1 95.3(5) . . ?
N1 O8 Lu1 95.3(5) 2_656 . ?
N1 O8 N1 0.0 2_656 . ?
O7 N1 O7 0.000(2) 2_656 . ?
O7 N1 O8 121.9(5) 2_656 2_656 ?
O7 N1 O8 121.9(5) . 2_656 ?
O7 N1 O8 121.9(5) . . ?
O7 N1 O8 121.9(5) 2_656 . ?
O8 N1 O8 116.2(10) 2_656 . ?
N1 N1 O7 0(10) 2_656 . ?
N1 N1 O7 0(10) 2_656 2_656 ?
N1 N1 O8 0(10) 2_656 . ?
N1 N1 O8 0(10) 2_656 2_656 ?
O1 N3 O6 114.9(7) . . ?
O3 N3 O1 123.8(9) . . ?
O3 N3 O6 121.3(9) . . ?
O2 N5 O4 113.7(6) . . ?
O5 N5 O2 123.0(9) . . ?
O5 N5 O4 123.3(8) . . ?
C1 N2 C5 125.0(14) . . ?
C1 N2 C6 108.9(9) . . ?
C6 N2 C5 126.1(15) . . ?
C1 N4 C2 125.8(9) . . ?
C1 N4 C4 110.2(10) . . ?
C4 N4 C2 124.0(10) . . ?
N2 C1 C3 127.6(11) . . ?
N4 C1 N2 106.4(9) . . ?
N4 C1 C3 126.0(12) . . ?
N4 C2 H2A 109.5 . . ?
N4 C2 H2B 109.5 . . ?
N4 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N4 C4 H4 126.1 . . ?
C6 C4 N4 107.9(9) . . ?
C6 C4 H4 126.1 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6 126.7 . . ?
C4 C6 N2 106.6(10) . . ?
C4 C6 H6 126.7 . . ?

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
Lu1 O1 N3 O3 179.0(9) . . . . ?
Lu1 O1 N3 O6 -0.8(8) . . . . ?
Lu1 O2 N5 O4 -4.2(6) . . . . ?
Lu1 O2 N5 O5 173.6(7) . . . . ?
Lu1 O4 N5 O2 4.4(6) . . . . ?
Lu1 O4 N5 O5 -173.5(7) . . . . ?
Lu1 O6 N3 O1 0.8(8) . . . . ?
Lu1 O6 N3 O3 -179.0(8) . . . . ?
Lu1 O8 N1 O7 180.000(3) . . . . ?
Lu1 O8 N1 O7 180.000(3) . . . 2_656 ?
Lu1 O8 N1 O8 -0.001(3) . . . 2_656 ?
Lu1 O8 N1 N1 0.0(13) . . . 2_656 ?
O7 O7 N1 O8 0(100) 2_656 . . 2_656 ?
O7 O7 N1 O8 0(100) 2_656 . . . ?
O7 O7 N1 N1 0.0 2_656 . . 2_656 ?
N1 O7 N1 O7 0(100) 2_656 . . 2_656 ?
N1 O7 N1 O8 0(100) 2_656 . . . ?
N1 O7 N1 O8 0(100) 2_656 . . 2_656 ?
N1 O8 N1 O7 0(100) 2_656 . . . ?
N1 O8 N1 O7 0(100) 2_656 . . 2_656 ?
N1 O8 N1 O8 0(100) 2_656 . . 2_656 ?
N4 C4 C6 N2 -0.1(13) . . . . ?
C1 N2 C6 C4 0.0(12) . . . . ?
C1 N4 C4 C6 0.2(12) . . . . ?
C2 N4 C1 N2 178.4(9) . . . . ?
C2 N4 C1 C3 -2.3(15) . . . . ?
C2 N4 C4 C6 -178.4(10) . . . . ?
C4 N4 C1 N2 -0.2(10) . . . . ?
C4 N4 C1 C3 179.2(9) . . . . ?
C5 N2 C1 N4 176.5(10) . . . . ?
C5 N2 C1 C3 -2.8(15) . . . . ?
C5 N2 C6 C4 -176.3(10) . . . . ?
C6 N2 C1 N4 0.1(10) . . . . ?
C6 N2 C1 C3 -179.2(10) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 71.326
_oxdiff_exptl_absorpt_empirical_full_min 0.352
####################################################################### 
# 
# 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_tgh-m3yb5
_database_code_depnum_ccdc_archive 'CCDC 2237588'
loop_
_audit_author_name
_audit_author_address
'Guo-Hong Tao'
;Sichuan University
China
;
_audit_update_record             
;
2023-05-21 deposited with the CCDC.	2023-05-26 downloaded from the CCDC.
;
_audit_creation_date             2023-05-19
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        '[MC1mim]2[Yb(NO3)5]'
_chemical_formula_moiety         'N5 O15 Yb, 2(C6 H11 N2)'
_chemical_formula_sum            'C12 H22 N9 O15 Yb'
_chemical_formula_weight         705.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H11N4.5O7.5Yb0.5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Yb Yb -7.2108 4.4329 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.5840(3)
_cell_length_b                   9.6554(2)
_cell_length_c                   15.4983(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.416(2)
_cell_angle_gamma                90
_cell_volume                     2480.91(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4556
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.8470
_cell_measurement_theta_min      5.2830
_shelx_estimated_absorpt_T_max   0.197
_shelx_estimated_absorpt_T_min   0.095
_exptl_absorpt_coefficient_mu    7.773
_exptl_absorpt_correction_T_max  0.270
_exptl_absorpt_correction_T_min  0.093
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.889
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1388
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 10 0.1768
-2 6 2 0.1867
2 -6 4 0.1345
4 5 -5 0.1485
3 4 -8 0.1799
-4 -5 5 0.1660
6 3 -7 0.1672
4 6 2 0.2136
-6 -3 -7 0.3185
-8 -3 4 0.2053
10 1 -4 0.1315
0 0 10 0.1701
11 1 1 0.1888
-10 -1 5 0.1997
-11 -1 0 0.1858
7 -3 -6 0.1572
6 -3 7 0.2124
9 -4 0 0.1568
-8 3 -3 0.1756
-1 2 -10 0.2091
6 0 -8 0.1616
-4 4 -6 0.1697
-5 5 -2 0.1719
6 -5 -1 0.1761
9 4 0 0.1957
5 -5 4 0.1723
1 -1 10 0.1761

_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.31
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9992 1.0002 10.0062 -0.0645 -0.1476 0.9966
-1.9989 6.0018 2.0063 -0.5458 -0.8046 0.2101
1.9995 -6.0019 3.9967 0.5349 0.8233 0.3863
4.0026 5.0008 -5.0015 -0.8169 -0.3204 -0.4934
3.0016 4.0007 -8.0030 -0.6330 -0.2819 -0.7921
-4.0026 -5.0008 5.0015 0.8169 0.3204 0.4934
6.0027 3.0000 -7.0050 -0.7205 0.0309 -0.6974
4.0035 6.0009 2.0027 -0.9419 -0.4119 0.2040
-6.0040 -2.9997 -7.0020 0.7459 -0.0745 -0.6943
-8.0038 -2.9997 4.0047 0.8580 -0.1712 0.4012
10.0040 0.9989 -4.0072 -0.7653 0.5287 -0.4063
0.0009 -0.0002 10.0050 -0.0181 0.0311 0.9941
11.0049 0.9986 0.9946 -0.8404 0.6097 0.0897
-10.0039 -0.9989 5.0077 0.7635 -0.5256 0.5057
-11.0048 -0.9986 0.0059 0.8386 -0.6066 0.0097
7.0014 -3.0017 -6.0092 -0.1141 0.7794 -0.6082
6.0022 -3.0018 6.9979 -0.0717 0.7545 0.6851
9.0025 -4.0023 -0.0081 -0.1447 1.0423 -0.0154
-8.0027 3.0020 -2.9947 0.1965 -0.8729 -0.2854
-1.0007 2.0009 -10.0030 -0.1406 -0.3232 -0.9900
6.0017 -0.0007 -8.0075 -0.3816 0.3678 -0.8014
-4.0010 4.0017 -5.9979 -0.1745 -0.7338 -0.5862
-5.0008 5.0020 -1.9946 -0.2281 -0.9001 -0.1860
6.0009 -5.0021 -1.0075 0.1676 0.9562 -0.1133
9.0048 3.9997 -0.0026 -1.0436 0.1358 -0.0030
5.0010 -5.0021 3.9956 0.2245 0.9063 0.3848
1.0010 -1.0006 10.0037 0.0282 0.2099 0.9915

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6741
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.065
_diffrn_reflns_theta_max         67.064
_diffrn_reflns_theta_min         5.302
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00 120.00   87
  2  ω     13.00 106.00   1.00    1.00    --   35.55  38.00  30.00   93
  3  ω    -33.00  54.00   1.00    1.00    --   35.55 -57.00-180.00   87
  4  ω     29.00  95.00   1.00    1.00    --   35.55-133.00 101.00   66
  5  ω    -33.00  54.00   1.00    1.00    --   35.55 -57.00 150.00   87
  6  ω    -33.00  54.00   1.00    1.00    --   35.55 -57.00 -60.00   87
  7  ω    -33.00  54.00   1.00    1.00    --   35.55 -57.00-120.00   87
  8  ω     57.00 150.00   1.00    1.93    --  108.00 178.00-120.00   93
  9  ω     37.00 115.00   1.00    1.93    --  108.00-111.00-150.00   78
 10  ω     38.00  98.00   1.00    1.93    --  108.00 -45.00 -30.00   60
 11  ω     38.00  98.00   1.00    1.93    --  108.00 -45.00  30.00   60
 12  ω     38.00  98.00   1.00    1.93    --  108.00 -45.00 -90.00   60
 13  ω     37.00  91.00   1.00    1.93    --  108.00 -30.00  30.00   54
 14  ω     38.00 109.00   1.00    1.93    --  108.00 -94.00 -90.00   71
 15  ω     37.00  91.00   1.00    1.93    --  108.00 -30.00-120.00   54
 16  ω     36.00 153.00   1.00    1.93    --  108.00 -15.00 120.00  117
 17  ω      7.00  60.00   1.00    1.00    --   35.55  77.00 -90.00   53
 18  ω     13.00 106.00   1.00    1.00    --   35.55  38.00 -90.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0660076000
_diffrn_orient_matrix_UB_12      -0.1123214000
_diffrn_orient_matrix_UB_13      -0.0018076000
_diffrn_orient_matrix_UB_21      0.0654074000
_diffrn_orient_matrix_UB_22      -0.1133129000
_diffrn_orient_matrix_UB_23      0.0031047000
_diffrn_orient_matrix_UB_31      -0.0009630000
_diffrn_orient_matrix_UB_32      0.0014764000
_diffrn_orient_matrix_UB_33      0.0993581000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2137
_reflns_number_total             2218
_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 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.059
_refine_diff_density_min         -1.158
_refine_diff_density_rms         0.136
_refine_ls_extinction_coef       0.0077(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0822P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1082
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 C5(H5A,H5B,H5C)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_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
Yb1 Yb 0.750000 0.32141(3) 0.500000 0.0408(2) Uani 1 2 d S T P . .
O1 O 0.6808(2) 0.1210(4) 0.4484(3) 0.0631(9) Uani 1 1 d . . . . .
O2 O 0.6096(3) 0.3031(5) 0.4514(3) 0.0698(12) Uani 1 1 d . . . . .
O3 O 0.5548(3) 0.1102(8) 0.4096(4) 0.1040(19) Uani 1 1 d . . . . .
O4 O 0.6675(2) 0.2663(5) 0.6180(2) 0.0620(9) Uani 1 1 d . . . . .
O5 O 0.6763(4) 0.3599(6) 0.7453(3) 0.0884(15) Uani 1 1 d . . . . .
O6 O 0.8135(3) 0.5423(4) 0.4911(3) 0.0680(10) Uani 1 1 d . . . . .
O7 O 0.750000 0.7364(8) 0.500000 0.128(4) Uani 1 2 d S T P . .
O8 O 0.7637(2) 0.4059(4) 0.6477(2) 0.0665(9) Uani 1 1 d . . . . .
N1 N 0.750000 0.6125(9) 0.500000 0.0731(19) Uani 1 2 d S T P . .
N4 N 0.7022(3) 0.3452(4) 0.6742(3) 0.0555(10) Uani 1 1 d . . . . .
N5 N 0.6131(4) 0.1753(5) 0.4353(4) 0.0637(14) Uani 1 1 d . . . . .
N2 N 0.6293(4) 0.8418(5) 0.7138(5) 0.0676(13) Uani 1 1 d . . . . .
N3 N 0.5854(3) 0.7756(8) 0.8352(4) 0.0834(17) Uani 1 1 d . . . . .
C1 C 0.5854(3) 0.8810(7) 0.7787(5) 0.0724(16) Uani 1 1 d . . . . .
C2 C 0.5406(6) 0.7737(18) 0.9160(7) 0.141(5) Uani 1 1 d . . . . .
H2A H 0.568967 0.827719 0.958913 0.211 Uiso 1 1 calc R U . . .
H2B H 0.535687 0.679978 0.935843 0.211 Uiso 1 1 calc R U . . .
H2C H 0.487805 0.812136 0.905782 0.211 Uiso 1 1 calc R U . . .
C3 C 0.6488(5) 0.9255(9) 0.6366(6) 0.096(2) Uani 1 1 d . . . . .
H3A H 0.600951 0.971121 0.615168 0.143 Uiso 1 1 calc R U . . .
H3B H 0.669318 0.865980 0.592638 0.143 Uiso 1 1 calc R U . . .
H3C H 0.688825 0.993565 0.652130 0.143 Uiso 1 1 calc R U . . .
C4 C 0.6577(4) 0.7111(7) 0.7283(6) 0.0768(18) Uani 1 1 d . . . . .
H4 H 0.690297 0.660401 0.691826 0.092 Uiso 1 1 calc R U . . .
C5 C 0.5438(6) 1.0158(10) 0.7844(8) 0.136(5) Uani 1 1 d . . . . .
H5A H 0.582847 1.089182 0.782778 0.203 Uiso 1 1 d R U . . .
H5B H 0.515377 1.020522 0.837508 0.203 Uiso 1 1 d R U . . .
H5C H 0.506297 1.025402 0.736628 0.203 Uiso 1 1 d R U . . .
C6 C 0.6308(5) 0.6695(7) 0.8032(7) 0.079(2) Uani 1 1 d . . . . .
H6 H 0.640627 0.584310 0.829486 0.095 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Yb1 O1 2.379(4) . ?
Yb1 O1 2.379(4) 2_656 ?
Yb1 O2 2.436(5) . ?
Yb1 O2 2.436(5) 2_656 ?
Yb1 O4 2.371(4) . ?
Yb1 O4 2.371(4) 2_656 ?
Yb1 O6 2.385(4) . ?
Yb1 O6 2.385(4) 2_656 ?
Yb1 O8 2.435(4) 2_656 ?
Yb1 O8 2.435(4) . ?
O1 N5 1.250(7) . ?
O2 N5 1.261(5) . ?
O3 N5 1.212(7) . ?
O4 N4 1.283(7) . ?
O5 N4 1.201(7) . ?
O6 N1 1.263(6) . ?
O6 N1 1.263(6) 2_656 ?
O7 N1 1.196(13) 2_656 ?
O7 N1 1.196(13) . ?
O8 N4 1.254(7) . ?
N1 N1 0.00000(2) 2_656 ?
N2 C1 1.312(10) . ?
N2 C3 1.486(10) . ?
N2 C4 1.364(8) . ?
N3 C1 1.342(11) . ?
N3 C2 1.472(12) . ?
N3 C6 1.371(10) . ?
C1 C5 1.477(10) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C6 1.318(13) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9601 . ?
C5 H5C 0.9601 . ?
C6 H6 0.9300 . ?

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 Yb1 O1 71.1(2) . 2_656 ?
O1 Yb1 O2 119.66(14) 2_656 . ?
O1 Yb1 O2 119.66(14) . 2_656 ?
O1 Yb1 O2 52.21(15) 2_656 2_656 ?
O1 Yb1 O2 52.21(15) . . ?
O1 Yb1 O6 122.47(15) 2_656 . ?
O1 Yb1 O6 156.72(16) 2_656 2_656 ?
O1 Yb1 O6 122.47(15) . 2_656 ?
O1 Yb1 O6 156.73(16) . . ?
O1 Yb1 O8 128.45(14) 2_656 2_656 ?
O1 Yb1 O8 85.59(14) . 2_656 ?
O1 Yb1 O8 128.45(14) . . ?
O1 Yb1 O8 85.59(14) 2_656 . ?
O2 Yb1 O2 171.7(2) 2_656 . ?
O4 Yb1 O1 80.85(14) . 2_656 ?
O4 Yb1 O1 80.85(14) 2_656 . ?
O4 Yb1 O1 78.12(14) 2_656 2_656 ?
O4 Yb1 O1 78.12(14) . . ?
O4 Yb1 O2 69.92(16) 2_656 2_656 ?
O4 Yb1 O2 69.92(16) . . ?
O4 Yb1 O2 108.11(16) . 2_656 ?
O4 Yb1 O2 108.11(16) 2_656 . ?
O4 Yb1 O4 154.1(2) 2_656 . ?
O4 Yb1 O6 120.62(15) 2_656 2_656 ?
O4 Yb1 O6 120.62(15) . . ?
O4 Yb1 O6 83.80(15) . 2_656 ?
O4 Yb1 O6 83.80(15) 2_656 . ?
O4 Yb1 O8 139.26(14) 2_656 . ?
O4 Yb1 O8 139.26(14) . 2_656 ?
O4 Yb1 O8 52.60(14) . . ?
O4 Yb1 O8 52.60(14) 2_656 2_656 ?
O6 Yb1 O2 117.86(15) 2_656 2_656 ?
O6 Yb1 O2 117.86(15) . . ?
O6 Yb1 O2 70.26(16) . 2_656 ?
O6 Yb1 O2 70.26(16) 2_656 . ?
O6 Yb1 O6 53.1(2) . 2_656 ?
O6 Yb1 O8 71.18(16) . 2_656 ?
O6 Yb1 O8 73.94(15) 2_656 2_656 ?
O6 Yb1 O8 71.18(16) 2_656 . ?
O6 Yb1 O8 73.94(15) . . ?
O8 Yb1 O2 112.41(16) 2_656 2_656 ?
O8 Yb1 O2 112.41(16) . . ?
O8 Yb1 O2 70.57(16) 2_656 . ?
O8 Yb1 O2 70.57(16) . 2_656 ?
O8 Yb1 O8 140.9(2) 2_656 . ?
N5 O1 Yb1 97.9(3) . . ?
N5 O2 Yb1 94.8(4) . . ?
N4 O4 Yb1 97.6(3) . . ?
N1 O6 Yb1 95.9(4) 2_656 . ?
N1 O6 Yb1 95.9(4) . . ?
N1 O6 N1 0.000(1) 2_656 . ?
N1 O7 N1 0.000(2) 2_656 . ?
N4 O8 Yb1 95.4(3) . . ?
O6 N1 O6 115.1(7) 2_656 . ?
O7 N1 O6 122.4(4) . 2_656 ?
O7 N1 O6 122.4(4) . . ?
N1 N1 O6 0(10) 2_656 2_656 ?
N1 N1 O6 0(10) 2_656 . ?
N1 N1 O7 0(10) 2_656 . ?
O5 N4 O4 121.9(6) . . ?
O5 N4 O8 124.0(6) . . ?
O8 N4 O4 114.1(4) . . ?
O1 N5 O2 115.1(5) . . ?
O3 N5 O1 122.8(6) . . ?
O3 N5 O2 122.1(7) . . ?
C1 N2 C3 126.6(6) . . ?
C1 N2 C4 109.6(7) . . ?
C4 N2 C3 123.7(7) . . ?
C1 N3 C2 124.9(10) . . ?
C1 N3 C6 108.8(6) . . ?
C6 N3 C2 126.2(10) . . ?
N2 C1 N3 106.9(6) . . ?
N2 C1 C5 124.7(9) . . ?
N3 C1 C5 128.4(8) . . ?
N3 C2 H2A 109.5 . . ?
N3 C2 H2B 109.5 . . ?
N3 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C4 H4 126.1 . . ?
C6 C4 N2 107.7(7) . . ?
C6 C4 H4 126.1 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N3 C6 H6 126.5 . . ?
C4 C6 N3 106.9(7) . . ?
C4 C6 H6 126.5 . . ?

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
Yb1 O1 N5 O2 1.4(6) . . . . ?
Yb1 O1 N5 O3 -178.1(6) . . . . ?
Yb1 O2 N5 O1 -1.4(5) . . . . ?
Yb1 O2 N5 O3 178.2(6) . . . . ?
Yb1 O4 N4 O5 174.3(5) . . . . ?
Yb1 O4 N4 O8 -4.6(5) . . . . ?
Yb1 O6 N1 O6 0.002(0) . . . 2_656 ?
Yb1 O6 N1 O7 180.000(0) . . . . ?
Yb1 O6 N1 N1 0(100) . . . 2_656 ?
Yb1 O8 N4 O4 4.5(4) . . . . ?
Yb1 O8 N4 O5 -174.4(5) . . . . ?
N1 O6 N1 O6 0(100) 2_656 . . 2_656 ?
N1 O6 N1 O7 0(100) 2_656 . . . ?
N1 O7 N1 O6 0(100) 2_656 . . . ?
N1 O7 N1 O6 0(56) 2_656 . . 2_656 ?
N2 C4 C6 N3 -0.1(9) . . . . ?
C1 N2 C4 C6 0.0(9) . . . . ?
C1 N3 C6 C4 0.1(9) . . . . ?
C2 N3 C1 N2 -177.4(7) . . . . ?
C2 N3 C1 C5 1.5(11) . . . . ?
C2 N3 C6 C4 177.4(7) . . . . ?
C3 N2 C1 N3 -178.0(7) . . . . ?
C3 N2 C1 C5 3.0(11) . . . . ?
C3 N2 C4 C6 178.2(7) . . . . ?
C4 N2 C1 N3 0.0(7) . . . . ?
C4 N2 C1 C5 -179.0(6) . . . . ?
C6 N3 C1 N2 -0.1(7) . . . . ?
C6 N3 C1 C5 178.9(7) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.382
_oxdiff_exptl_absorpt_empirical_full_min 0.777
####################################################################### 
# 
# 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_tgh-h-tm-8
_database_code_depnum_ccdc_archive 'CCDC 2237585'
loop_
_audit_author_name
_audit_author_address
'Guo-Hong Tao'
;Sichuan University
China
;
_audit_update_record             
;
2023-05-21 deposited with the CCDC.	2023-05-26 downloaded from the CCDC.
;
_audit_creation_date             2023-05-19
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        '[MC1mim]2[Tm(NO3)5]'
_chemical_formula_moiety         'N5 O15 Tm, 2(C6 H11 N2)'
_chemical_formula_sum            'C12 H22 N9 O15 Tm'
_chemical_formula_weight         701.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H22N9O15Tm
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tm Tm -8.0393 4.1821 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.5968(4)
_cell_length_b                   9.6698(3)
_cell_length_c                   15.4989(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.436(2)
_cell_angle_gamma                90
_cell_volume                     2486.60(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6037
_cell_measurement_temperature    289(16)
_cell_measurement_theta_max      72.4720
_cell_measurement_theta_min      3.8620
_shelx_estimated_absorpt_T_max   0.134
_shelx_estimated_absorpt_T_min   0.051
_exptl_absorpt_coefficient_mu    7.482
_exptl_absorpt_correction_T_max  0.213
_exptl_absorpt_correction_T_min  0.029
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.873
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1384
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 0 -1 0.2026
-2 0 1 0.2433
1 2 -1 0.3272
1 -1 2 0.2979
0 -1 1 0.1790
1 2 1 0.4149
1 0 -2 0.3551
-2 -2 1 0.2413
-1 0 -2 0.3287
-1 -2 2 0.1755
-1 -1 1 0.1644

_exptl_crystal_size_max          0.98
_exptl_crystal_size_mid          0.75
_exptl_crystal_size_min          0.45
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.0005 0.0006 -0.9973 0.2004 0.0529 -0.0211
-2.0005 -0.0006 0.9973 -0.2004 -0.0529 0.0211
0.9981 2.0016 -1.0003 0.0934 0.0128 -0.3328
0.9994 -1.0001 2.0009 -0.0428 0.1996 0.1812
0.0005 -1.0006 1.0004 -0.0454 0.0623 0.1713
0.9963 2.0019 0.9986 -0.0367 0.1607 -0.3056
1.0016 0.0001 -1.9978 0.1978 -0.0844 -0.0310
-1.9979 -2.0020 0.9993 -0.1611 -0.0762 0.3365
-0.9981 -0.0006 -1.9999 0.0624 -0.2113 -0.0235
-0.9989 -2.0015 1.9997 -0.1585 0.0611 0.3464
-0.9994 -1.0009 0.9993 -0.1131 -0.0011 0.1751

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0907
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7266
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.608
_diffrn_reflns_theta_min         5.295
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      289(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  63.00   1.00    1.00    --   36.29 -77.00-120.00   94
  2  ω    -31.00  63.00   1.00    1.00    --   36.29 -77.00-150.00   94
  3  ω    -31.00  63.00   1.00    1.00    --   36.29 -77.00 -60.00   94
  4  ω     20.00 104.00   1.00    1.00    --   36.29  57.00  90.00   84
  5  ω      1.00  75.00   1.00    1.00    --   36.29 -99.00-180.00   74
  6  ω    -33.00  55.00   1.00    1.00    --   36.29 -38.00 120.00   88
  7  ω     38.00  91.00   1.00    1.00    --  108.00 -30.00  90.00   53
  8  ω     38.00  91.00   1.00    1.00    --  108.00 -30.00  60.00   53
  9  ω     39.00 109.00   1.00    1.00    --  108.00 -94.00-150.00   70
 10  ω     38.00  91.00   1.00    1.00    --  108.00 -30.00  30.00   53
 11  ω     40.00  98.00   1.00    1.00    --  108.00 -45.00-180.00   58
 12  ω     39.00 109.00   1.00    1.00    --  108.00 -94.00 -60.00   70
 13  ω     39.00 109.00   1.00    1.00    --  108.00 -94.00 150.00   70
 14  ω     37.00 146.00   1.00    1.00    --  108.00 -15.00 -60.00  109
 15  ω     17.00 105.00   1.00    1.00    --   36.29  38.00-150.00   88
 16  ω     20.00 104.00   1.00    1.00    --   36.29  57.00   0.00   84
 17  ω      1.00  75.00   1.00    1.00    --   36.29 -99.00  60.00   74
 18  ω    -33.00  55.00   1.00    1.00    --   36.29 -38.00  30.00   88
 19  ω     10.00 104.00   1.00    1.00    --   36.29  77.00-120.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0677791000
_diffrn_orient_matrix_UB_12      -0.0196369000
_diffrn_orient_matrix_UB_13      -0.0650365000
_diffrn_orient_matrix_UB_21      0.0633449000
_diffrn_orient_matrix_UB_22      0.0118008000
_diffrn_orient_matrix_UB_23      0.0740214000
_diffrn_orient_matrix_UB_31      -0.0037075000
_diffrn_orient_matrix_UB_32      -0.1576013000
_diffrn_orient_matrix_UB_33      0.0136385000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2279
_reflns_number_total             2420
_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 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.213
_refine_diff_density_min         -1.194
_refine_diff_density_rms         0.132
_refine_ls_extinction_coef       0.0044(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2420
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0920P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1354
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 N2, C6
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 O2, N4, O5, O6
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6)
3.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_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
Tm1 Tm 0.250000 0.32113(3) 0.500000 0.0484(2) Uani 1 2 d S T P . .
O1 O 0.1798(3) 0.1198(5) 0.4489(3) 0.0717(10) Uani 1 1 d . . . . .
O2 O 0.2370(3) 0.4059(5) 0.3521(3) 0.0728(10) Uani 1 1 d . U . . .
O3 O 0.0542(4) 0.1101(9) 0.4098(4) 0.113(2) Uani 1 1 d . . . . .
O4 O 0.1096(3) 0.3021(6) 0.4510(4) 0.0758(13) Uani 1 1 d . . . . .
O5 O 0.3237(4) 0.3609(6) 0.2541(3) 0.0942(15) Uani 1 1 d . U . . .
O6 O 0.3327(3) 0.2664(5) 0.3813(3) 0.0714(10) Uani 1 1 d . U . . .
O7 O 0.250000 0.7373(9) 0.500000 0.126(4) Uani 1 2 d S T P . .
O8 O 0.3144(3) 0.5438(4) 0.4909(3) 0.0753(11) Uani 1 1 d . . . . .
N1 N 0.250000 0.6119(9) 0.500000 0.080(2) Uani 1 2 d S T P . .
N4 N 0.2984(4) 0.3452(5) 0.3262(3) 0.0622(9) Uani 1 1 d . U . . .
N5 N 0.1125(4) 0.1756(6) 0.4350(4) 0.0730(17) Uani 1 1 d . . . . .
N2 N 0.4150(4) 0.7772(9) 0.1652(5) 0.0902(18) Uani 1 1 d . U . . .
N3 N 0.3706(4) 0.8415(6) 0.2862(5) 0.0748(15) Uani 1 1 d . . . . .
C1 C 0.4147(4) 0.8818(9) 0.2207(5) 0.0791(18) Uani 1 1 d . . . . .
C2 C 0.4565(6) 1.0169(11) 0.2150(9) 0.140(5) Uani 1 1 d . . . . .
H2A H 0.420732 1.089323 0.232257 0.211 Uiso 1 1 calc R U . . .
H2B H 0.472278 1.032459 0.156652 0.211 Uiso 1 1 calc R U . . .
H2C H 0.503410 1.016327 0.252455 0.211 Uiso 1 1 calc R U . . .
C3 C 0.3513(6) 0.9261(9) 0.3623(6) 0.101(2) Uani 1 1 d . . . . .
H3A H 0.396747 0.983240 0.377781 0.151 Uiso 1 1 calc R U . . .
H3B H 0.339131 0.866551 0.409797 0.151 Uiso 1 1 calc R U . . .
H3C H 0.305551 0.983636 0.348876 0.151 Uiso 1 1 calc R U . . .
C4 C 0.3420(5) 0.7120(8) 0.2707(6) 0.082(2) Uani 1 1 d . . . . .
H4 H 0.308598 0.661445 0.306323 0.098 Uiso 1 1 calc R U . . .
C5 C 0.4592(7) 0.773(2) 0.0854(7) 0.152(5) Uani 1 1 d . . . . .
H5A H 0.435725 0.704683 0.047518 0.227 Uiso 1 1 calc R U . . .
H5B H 0.514464 0.749726 0.097966 0.227 Uiso 1 1 calc R U . . .
H5C H 0.456557 0.862021 0.057946 0.227 Uiso 1 1 calc R U . . .
C6 C 0.3699(6) 0.6708(8) 0.1962(7) 0.089(2) Uani 1 1 d . U . . .
H6 H 0.360730 0.585707 0.169824 0.107 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tm1 O1 2.393(4) . ?
Tm1 O1 2.393(4) 2_556 ?
Tm1 O2 2.439(4) . ?
Tm1 O2 2.439(4) 2_556 ?
Tm1 O4 2.439(5) 2_556 ?
Tm1 O4 2.439(5) . ?
Tm1 O6 2.383(4) . ?
Tm1 O6 2.383(4) 2_556 ?
Tm1 O8 2.409(4) . ?
Tm1 O8 2.409(4) 2_556 ?
O1 N5 1.255(8) . ?
O2 N4 1.252(7) . ?
O3 N5 1.212(8) . ?
O4 N5 1.249(6) . ?
O5 N4 1.214(7) . ?
O6 N4 1.268(7) . ?
O7 N1 1.212(14) . ?
O7 N1 1.212(14) 2_556 ?
O8 N1 1.266(6) 2_556 ?
O8 N1 1.266(6) . ?
N1 N1 0.000(18) 2_556 ?
N2 C1 1.328(11) . ?
N2 C5 1.455(12) . ?
N2 C6 1.367(11) . ?
N3 C1 1.326(10) . ?
N3 C3 1.477(10) . ?
N3 C4 1.359(9) . ?
C1 C2 1.482(11) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C6 1.316(13) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6 0.9300 . ?

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 Tm1 O1 71.2(2) . 2_556 ?
O1 Tm1 O2 86.05(17) 2_556 2_556 ?
O1 Tm1 O2 127.99(15) . 2_556 ?
O1 Tm1 O2 127.99(15) 2_556 . ?
O1 Tm1 O2 86.05(17) . . ?
O1 Tm1 O4 119.66(17) 2_556 . ?
O1 Tm1 O4 51.85(17) 2_556 2_556 ?
O1 Tm1 O4 51.85(17) . . ?
O1 Tm1 O4 119.66(17) . 2_556 ?
O1 Tm1 O8 156.97(19) 2_556 2_556 ?
O1 Tm1 O8 156.97(19) . . ?
O1 Tm1 O8 122.23(18) . 2_556 ?
O1 Tm1 O8 122.23(18) 2_556 . ?
O2 Tm1 O2 140.7(2) . 2_556 ?
O2 Tm1 O4 112.30(17) . 2_556 ?
O2 Tm1 O4 70.81(17) 2_556 2_556 ?
O2 Tm1 O4 70.81(17) . . ?
O2 Tm1 O4 112.30(17) 2_556 . ?
O4 Tm1 O4 171.3(3) . 2_556 ?
O6 Tm1 O1 81.29(16) 2_556 2_556 ?
O6 Tm1 O1 77.88(16) . 2_556 ?
O6 Tm1 O1 77.88(16) 2_556 . ?
O6 Tm1 O1 81.29(17) . . ?
O6 Tm1 O2 139.58(16) . 2_556 ?
O6 Tm1 O2 139.58(16) 2_556 . ?
O6 Tm1 O2 52.27(15) . . ?
O6 Tm1 O2 52.26(16) 2_556 2_556 ?
O6 Tm1 O4 107.88(18) . . ?
O6 Tm1 O4 70.09(17) 2_556 . ?
O6 Tm1 O4 70.09(17) . 2_556 ?
O6 Tm1 O4 107.87(18) 2_556 2_556 ?
O6 Tm1 O6 154.3(3) . 2_556 ?
O6 Tm1 O8 120.57(17) . 2_556 ?
O6 Tm1 O8 83.59(18) . . ?
O6 Tm1 O8 120.57(17) 2_556 . ?
O6 Tm1 O8 83.59(18) 2_556 2_556 ?
O8 Tm1 O2 70.95(17) . . ?
O8 Tm1 O2 74.08(17) . 2_556 ?
O8 Tm1 O2 74.08(17) 2_556 . ?
O8 Tm1 O2 70.95(17) 2_556 2_556 ?
O8 Tm1 O4 118.09(18) 2_556 2_556 ?
O8 Tm1 O4 118.08(17) . . ?
O8 Tm1 O4 70.38(18) 2_556 . ?
O8 Tm1 O4 70.38(18) . 2_556 ?
O8 Tm1 O8 53.3(2) 2_556 . ?
N5 O1 Tm1 97.5(4) . . ?
N4 O2 Tm1 95.1(3) . . ?
N5 O4 Tm1 95.5(5) . . ?
N4 O6 Tm1 97.4(3) . . ?
N1 O7 N1 0.000(2) 2_556 . ?
N1 O8 Tm1 94.7(4) 2_556 . ?
N1 O8 Tm1 94.7(4) . . ?
N1 O8 N1 0.000(1) 2_556 . ?
O7 N1 O8 121.4(4) . 2_556 ?
O7 N1 O8 121.4(4) . . ?
O8 N1 O8 117.3(8) 2_556 . ?
N1 N1 O7 0(10) 2_556 . ?
N1 N1 O8 0(10) 2_556 2_556 ?
N1 N1 O8 0(10) 2_556 . ?
O2 N4 O6 115.0(5) . . ?
O5 N4 O2 122.7(6) . . ?
O5 N4 O6 122.4(6) . . ?
O3 N5 O1 122.0(7) . . ?
O3 N5 O4 122.8(8) . . ?
O4 N5 O1 115.1(6) . . ?
C1 N2 C5 125.6(11) . . ?
C1 N2 C6 109.6(7) . . ?
C6 N2 C5 124.8(11) . . ?
C1 N3 C3 125.7(7) . . ?
C1 N3 C4 109.4(8) . . ?
C4 N3 C3 124.8(7) . . ?
N2 C1 C2 128.6(9) . . ?
N3 C1 N2 106.5(7) . . ?
N3 C1 C2 124.9(9) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N3 C3 H3A 109.5 . . ?
N3 C3 H3B 109.5 . . ?
N3 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N3 C4 H4 126.1 . . ?
C6 C4 N3 107.7(8) . . ?
C6 C4 H4 126.1 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6 126.6 . . ?
C4 C6 N2 106.8(8) . . ?
C4 C6 H6 126.6 . . ?

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
Tm1 O1 N5 O3 -177.7(6) . . . . ?
Tm1 O1 N5 O4 0.7(6) . . . . ?
Tm1 O2 N4 O5 -174.9(5) . . . . ?
Tm1 O2 N4 O6 4.8(5) . . . . ?
Tm1 O4 N5 O1 -0.7(6) . . . . ?
Tm1 O4 N5 O3 177.7(6) . . . . ?
Tm1 O6 N4 O2 -4.9(5) . . . . ?
Tm1 O6 N4 O5 174.8(5) . . . . ?
Tm1 O8 N1 O7 180.000(0) . . . . ?
Tm1 O8 N1 O8 0.000(1) . . . 2_556 ?
Tm1 O8 N1 N1 0(100) . . . 2_556 ?
N1 O7 N1 O8 0(100) 2_556 . . . ?
N1 O7 N1 O8 0(53) 2_556 . . 2_556 ?
N1 O8 N1 O7 0(100) 2_556 . . . ?
N1 O8 N1 O8 0(100) 2_556 . . 2_556 ?
N3 C4 C6 N2 -1.0(10) . . . . ?
C1 N2 C6 C4 0.3(10) . . . . ?
C1 N3 C4 C6 1.4(10) . . . . ?
C3 N3 C1 N2 -178.0(7) . . . . ?
C3 N3 C1 C2 3.9(12) . . . . ?
C3 N3 C4 C6 178.2(8) . . . . ?
C4 N3 C1 N2 -1.2(8) . . . . ?
C4 N3 C1 C2 -179.3(7) . . . . ?
C5 N2 C1 N3 -176.9(8) . . . . ?
C5 N2 C1 C2 1.1(12) . . . . ?
C5 N2 C6 C4 177.8(8) . . . . ?
C6 N2 C1 N3 0.6(8) . . . . ?
C6 N2 C1 C2 178.6(8) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.136
_oxdiff_exptl_absorpt_empirical_full_min 0.423
