# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_YbTrenovan
_database_code_depnum_ccdc_archive 'CCDC 2234248'
loop_
_audit_author_name
_audit_author_address
'Christian Dirk Buch'
;University of Copenhagen
Denmark
;
_audit_update_record             
;
2023-01-04 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_audit_creation_date             2021-08-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1(C30 H33 N4 O6 Yb1)'
_chemical_formula_sum            'C30 H33 N4 O6 Yb'
_chemical_formula_weight         718.65
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Yb Yb -0.3850 5.5486 '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      trigonal
_space_group_IT_number           147
_space_group_name_H-M_alt        'P -3'
_space_group_name_Hall           '-P 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'

_cell_length_a                   13.9911(5)
_cell_length_b                   13.9911(5)
_cell_length_c                   8.1853(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1387.61(11)
_cell_formula_units_Z            1.99998
_cell_measurement_reflns_used    9851
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.694
_cell_measurement_theta_min      2.489
_shelx_estimated_absorpt_T_max   0.472
_shelx_estimated_absorpt_T_min   0.330
_exptl_absorpt_coefficient_mu    3.422
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.4603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1298 before and 0.0532 after correction. The Ratio of minimum to maximum transmission is 0.6172. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             718
_exptl_crystal_size_max          0.417
_exptl_crystal_size_mid          0.271
_exptl_crystal_size_min          0.258
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.999
_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       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            21437
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.269
_diffrn_reflns_theta_min         2.488
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2144
_reflns_number_total             2298
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.801
_refine_diff_density_min         -0.769
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         2298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0189
_refine_ls_R_factor_gt           0.0161
_refine_ls_restrained_S_all      1.149
_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)+(0.0140P)²+0.8136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0365
_refine_ls_wR_factor_ref         0.0376
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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
Yb1 Yb 0.333333 0.666667 0.39324(2) 0.01374(5) Uani 1 3 d S T P . .
O1 O 0.47288(10) 0.67875(10) 0.25918(15) 0.0172(3) Uani 1 1 d . . . . .
O2 O 0.57209(11) 0.63180(11) 0.02110(16) 0.0218(3) Uani 1 1 d . . . . .
N2 N 0.49498(13) 0.81487(13) 0.52318(19) 0.0201(3) Uani 1 1 d . . . . .
N1 N 0.333333 0.666667 0.7444(3) 0.0234(6) Uani 1 3 d S T P . .
C5 C 0.57998(14) 0.73649(14) 0.2512(2) 0.0155(3) Uani 1 1 d . . . . .
C4 C 0.64567(15) 0.82245(15) 0.3629(2) 0.0183(3) Uani 1 1 d . . . . .
C6 C 0.63822(15) 0.71539(15) 0.1254(2) 0.0176(3) Uani 1 1 d . . . . .
C3 C 0.59812(16) 0.85553(15) 0.4925(2) 0.0206(4) Uani 1 1 d . . . . .
H3 H 0.648327 0.913229 0.562093 0.025 Uiso 1 1 calc R . . . .
C9 C 0.76213(16) 0.88216(16) 0.3483(3) 0.0239(4) Uani 1 1 d . . . . .
H9 H 0.804585 0.939418 0.424010 0.029 Uiso 1 1 calc R . . . .
C7 C 0.75198(16) 0.77520(16) 0.1142(2) 0.0228(4) Uani 1 1 d . . . . .
H7 H 0.788276 0.759562 0.029102 0.027 Uiso 1 1 calc R . . . .
C1 C 0.43258(19) 0.76819(19) 0.8010(2) 0.0299(5) Uani 1 1 d . . . . .
H1A H 0.493049 0.752522 0.822451 0.036 Uiso 1 1 calc R . . . .
H1B H 0.415982 0.794134 0.903926 0.036 Uiso 1 1 calc R . . . .
C2 C 0.46811(17) 0.85692(17) 0.6707(2) 0.0263(4) Uani 1 1 d . . . . .
H2A H 0.407712 0.872407 0.647485 0.032 Uiso 1 1 calc R . . . .
H2B H 0.533491 0.926032 0.707884 0.032 Uiso 1 1 calc R . . . .
C10 C 0.62776(17) 0.60892(18) -0.1064(2) 0.0267(4) Uani 1 1 d . . . . .
H10A H 0.662396 0.672006 -0.181172 0.040 Uiso 1 1 calc GR . . . .
H10B H 0.574435 0.543123 -0.166671 0.040 Uiso 1 1 calc GR . . . .
H10C H 0.684555 0.595973 -0.058788 0.040 Uiso 1 1 calc GR . . . .
C8 C 0.81421(16) 0.85869(17) 0.2273(3) 0.0260(4) Uani 1 1 d . . . . .
H8 H 0.892441 0.898816 0.219716 0.031 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Yb1 O1 2.1712(12) 2_665 ?
Yb1 O1 2.1712(12) 3_565 ?
Yb1 O1 2.1712(12) . ?
Yb1 N2 2.4200(15) 2_665 ?
Yb1 N2 2.4199(16) . ?
Yb1 N2 2.4200(15) 3_565 ?
Yb1 N1 2.875(3) . ?
O1 C5 1.301(2) . ?
O2 C6 1.368(2) . ?
O2 C10 1.431(2) . ?
N2 C3 1.284(2) . ?
N2 C2 1.472(2) . ?
N1 C1 1.479(2) 2_665 ?
N1 C1 1.479(2) . ?
N1 C1 1.479(2) 3_565 ?
C5 C4 1.422(2) . ?
C5 C6 1.432(2) . ?
C4 C3 1.446(3) . ?
C4 C9 1.416(3) . ?
C6 C7 1.382(3) . ?
C9 C8 1.364(3) . ?
C7 C8 1.401(3) . ?
C1 C2 1.520(3) . ?

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 96.71(4) 2_665 3_565 ?
O1 Yb1 O1 96.71(4) 2_665 . ?
O1 Yb1 O1 96.71(4) 3_565 . ?
O1 Yb1 N2 171.16(5) 3_565 . ?
O1 Yb1 N2 171.16(5) . 2_665 ?
O1 Yb1 N2 171.16(5) 2_665 3_565 ?
O1 Yb1 N2 74.73(5) 2_665 2_665 ?
O1 Yb1 N2 86.65(5) 2_665 . ?
O1 Yb1 N2 86.65(5) 3_565 2_665 ?
O1 Yb1 N2 86.65(5) . 3_565 ?
O1 Yb1 N2 74.73(5) . . ?
O1 Yb1 N2 74.73(5) 3_565 3_565 ?
O1 Yb1 N1 120.36(3) 2_665 . ?
O1 Yb1 N1 120.36(3) 3_565 . ?
O1 Yb1 N1 120.36(3) . . ?
N2 Yb1 N2 102.14(5) 2_665 . ?
N2 Yb1 N2 102.13(5) . 3_565 ?
N2 Yb1 N2 102.14(5) 2_665 3_565 ?
N2 Yb1 N1 63.93(4) 3_565 . ?
N2 Yb1 N1 63.93(4) 2_665 . ?
N2 Yb1 N1 63.93(4) . . ?
C5 O1 Yb1 141.78(12) . . ?
C6 O2 C10 115.82(15) . . ?
C3 N2 Yb1 130.96(13) . . ?
C3 N2 C2 116.01(16) . . ?
C2 N2 Yb1 112.77(12) . . ?
C1 N1 Yb1 108.24(13) 3_565 . ?
C1 N1 Yb1 108.24(13) . . ?
C1 N1 Yb1 108.24(13) 2_665 . ?
C1 N1 C1 110.67(13) . 3_565 ?
C1 N1 C1 110.67(13) 2_665 3_565 ?
C1 N1 C1 110.67(13) 2_665 . ?
O1 C5 C4 123.36(16) . . ?
O1 C5 C6 120.38(16) . . ?
C4 C5 C6 116.27(16) . . ?
C5 C4 C3 122.43(16) . . ?
C9 C4 C5 120.77(17) . . ?
C9 C4 C3 116.78(17) . . ?
O2 C6 C5 114.43(15) . . ?
O2 C6 C7 123.93(17) . . ?
C7 C6 C5 121.64(17) . . ?
N2 C3 C4 126.64(17) . . ?
C8 C9 C4 120.98(18) . . ?
C6 C7 C8 120.57(18) . . ?
N1 C1 C2 109.35(17) . . ?
N2 C2 C1 107.09(16) . . ?
C9 C8 C7 119.77(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_YbTrenpvan
_database_code_depnum_ccdc_archive 'CCDC 2234249'
loop_
_audit_author_name
_audit_author_address
'Christian Dirk Buch'
;University of Copenhagen
Denmark
;
_audit_update_record             
;
2023-01-04 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_audit_creation_date             2021-08-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1(C30 H33 N4 O6 Yb1)'
_chemical_formula_sum            'C30 H33 N4 O6 Yb'
_chemical_formula_weight         718.65
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Yb Yb -0.3850 5.5486 '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      trigonal
_space_group_IT_number           147
_space_group_name_H-M_alt        'P -3'
_space_group_name_Hall           '-P 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'

_cell_length_a                   14.7420(5)
_cell_length_b                   14.7420(5)
_cell_length_c                   7.5448(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1420.01(12)
_cell_formula_units_Z            1.99998
_cell_measurement_reflns_used    9831
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.103
_cell_measurement_theta_min      2.764
_shelx_estimated_absorpt_T_max   0.659
_shelx_estimated_absorpt_T_min   0.333
_exptl_absorpt_coefficient_mu    3.343
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.4689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1481 before and 0.0766 after correction. The Ratio of minimum to maximum transmission is 0.6287. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             718
_exptl_crystal_size_max          0.422
_exptl_crystal_size_mid          0.247
_exptl_crystal_size_min          0.136
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            19885
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.860
_diffrn_reflns_theta_min         2.763
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2129
_reflns_number_total             2254
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.532
_refine_diff_density_min         -1.123
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         2254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0186
_refine_ls_R_factor_gt           0.0167
_refine_ls_restrained_S_all      1.077
_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)+(0.0161P)²+0.9252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0405
_refine_ls_wR_factor_ref         0.0413
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C9(H9), C7(H7)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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
Yb1 Yb 0.666667 0.333333 0.56020(2) 0.00693(5) Uani 1 3 d S T P . .
O1 O 0.74679(10) 0.27067(10) 0.40619(17) 0.0111(3) Uani 1 1 d . . . . .
O2 O 0.71060(13) -0.10851(12) 0.2173(2) 0.0206(3) Uani 1 1 d . . . . .
N1 N 0.666667 0.333333 0.9124(4) 0.0092(5) Uani 1 3 d S T P . .
N2 N 0.60494(12) 0.16035(12) 0.6798(2) 0.0102(3) Uani 1 1 d . . . . .
C5 C 0.73766(14) 0.17988(15) 0.3667(2) 0.0098(3) Uani 1 1 d . . . . .
C1 C 0.62935(15) 0.22506(15) 0.9783(2) 0.0127(4) Uani 1 1 d . . . . .
H1A H 0.596395 0.216080 1.096210 0.015 Uiso 1 1 calc R . . . .
H1B H 0.689545 0.213322 0.991142 0.015 Uiso 1 1 calc R . . . .
C4 C 0.66915(14) 0.08571(14) 0.4588(2) 0.0102(3) Uani 1 1 d . . . . .
C6 C 0.79881(15) 0.17303(15) 0.2287(2) 0.0123(4) Uani 1 1 d . . . . .
H6 H 0.847018 0.234956 0.167502 0.015 Uiso 1 1 calc R . . . .
C2 C 0.55065(15) 0.14599(15) 0.8497(2) 0.0120(4) Uani 1 1 d . . . . .
H2A H 0.524141 0.073933 0.894500 0.014 Uiso 1 1 calc R . . . .
H2B H 0.490537 0.157673 0.834864 0.014 Uiso 1 1 calc R . . . .
C8 C 0.72123(16) -0.01303(15) 0.2698(3) 0.0140(4) Uani 1 1 d . . . . .
C3 C 0.61038(15) 0.08300(15) 0.6152(2) 0.0114(4) Uani 1 1 d . . . . .
H3 H 0.572501 0.017784 0.674940 0.014 Uiso 1 1 calc R . . . .
C9 C 0.66224(15) -0.00959(15) 0.4080(2) 0.0128(4) Uani 1 1 d . . . . .
H9 H 0.616319 -0.072106 0.470004 0.015 Uiso 1 1 calc R . . . .
C7 C 0.79037(16) 0.07871(16) 0.1803(2) 0.0144(4) Uani 1 1 d . . . . .
H7 H 0.831766 0.076331 0.085897 0.017 Uiso 1 1 calc R . . . .
C10 C 0.7870(2) -0.12778(19) 0.2968(3) 0.0263(5) Uani 1 1 d . . . . .
H10A H 0.857149 -0.072946 0.261077 0.039 Uiso 1 1 calc GR . . . .
H10B H 0.775579 -0.196143 0.258056 0.039 Uiso 1 1 calc GR . . . .
H10C H 0.780704 -0.127502 0.426120 0.039 Uiso 1 1 calc GR . . . .


_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 2.1656(13) . ?
Yb1 O1 2.1656(13) 3_665 ?
Yb1 O1 2.1656(13) 2_655 ?
Yb1 N1 2.657(3) . ?
Yb1 N2 2.4135(16) 3_665 ?
Yb1 N2 2.4135(16) . ?
Yb1 N2 2.4136(16) 2_655 ?
O1 C5 1.311(2) . ?
O2 C8 1.394(2) . ?
O2 C10 1.424(3) . ?
N1 C1 1.490(2) 2_655 ?
N1 C1 1.490(2) . ?
N1 C1 1.490(2) 3_665 ?
N2 C2 1.469(2) . ?
N2 C3 1.279(2) . ?
C5 C4 1.424(3) . ?
C5 C6 1.413(3) . ?
C1 C2 1.515(3) . ?
C4 C3 1.453(3) . ?
C4 C9 1.410(3) . ?
C6 C7 1.382(3) . ?
C8 C9 1.375(3) . ?
C8 C7 1.395(3) . ?

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 93.91(5) . 3_665 ?
O1 Yb1 O1 93.91(5) . 2_655 ?
O1 Yb1 O1 93.91(5) 3_665 2_655 ?
O1 Yb1 N1 122.45(4) 3_665 . ?
O1 Yb1 N1 122.45(4) 2_655 . ?
O1 Yb1 N1 122.45(4) . . ?
O1 Yb1 N2 82.77(5) . 2_655 ?
O1 Yb1 N2 168.49(5) . 3_665 ?
O1 Yb1 N2 168.49(5) 3_665 2_655 ?
O1 Yb1 N2 82.78(5) 2_655 3_665 ?
O1 Yb1 N2 168.49(5) 2_655 . ?
O1 Yb1 N2 75.39(5) 3_665 3_665 ?
O1 Yb1 N2 75.40(5) 2_655 2_655 ?
O1 Yb1 N2 82.78(5) 3_665 . ?
O1 Yb1 N2 75.39(5) . . ?
N2 Yb1 N1 68.04(4) 2_655 . ?
N2 Yb1 N1 68.04(4) . . ?
N2 Yb1 N1 68.04(4) 3_665 . ?
N2 Yb1 N2 106.87(4) 2_655 3_665 ?
N2 Yb1 N2 106.87(4) . 3_665 ?
N2 Yb1 N2 106.87(4) . 2_655 ?
C5 O1 Yb1 139.30(12) . . ?
C8 O2 C10 112.37(16) . . ?
C1 N1 Yb1 109.50(12) 2_655 . ?
C1 N1 Yb1 109.50(12) 3_665 . ?
C1 N1 Yb1 109.50(12) . . ?
C1 N1 C1 109.44(12) 2_655 3_665 ?
C1 N1 C1 109.44(12) 2_655 . ?
C1 N1 C1 109.44(12) . 3_665 ?
C2 N2 Yb1 111.65(11) . . ?
C3 N2 Yb1 129.85(13) . . ?
C3 N2 C2 118.46(16) . . ?
O1 C5 C4 123.02(17) . . ?
O1 C5 C6 119.80(17) . . ?
C6 C5 C4 117.17(17) . . ?
N1 C1 C2 109.94(16) . . ?
C5 C4 C3 123.08(17) . . ?
C9 C4 C5 120.11(17) . . ?
C9 C4 C3 116.63(17) . . ?
C7 C6 C5 121.77(18) . . ?
N2 C2 C1 107.19(15) . . ?
O2 C8 C7 120.00(18) . . ?
C9 C8 O2 119.96(18) . . ?
C9 C8 C7 120.03(18) . . ?
N2 C3 C4 125.98(17) . . ?
C8 C9 C4 120.72(18) . . ?
C6 C7 C8 120.16(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_Ybtrenpvan_300K
_database_code_depnum_ccdc_archive 'CCDC 2236957'
loop_
_audit_author_name
_audit_author_address
'Christian Dirk Buch'
;University of Copenhagen
Denmark
;
_audit_update_record             
;
2023-01-18 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_audit_creation_date             2023-01-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H33 N4 O6 Yb'
_chemical_formula_sum            'C30 H33 N4 O6 Yb'
_chemical_formula_weight         718.64
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Yb Yb -0.3850 5.5486 '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      trigonal
_space_group_IT_number           147
_space_group_name_H-M_alt        'P -3'
_space_group_name_Hall           '-P 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'

_cell_length_a                   14.7657(6)
_cell_length_b                   14.7657(6)
_cell_length_c                   7.7216(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1457.96(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9917
_cell_measurement_temperature    300
_cell_measurement_theta_max      27.334
_cell_measurement_theta_min      2.638
_shelx_estimated_absorpt_T_max   0.774
_shelx_estimated_absorpt_T_min   0.562
_exptl_absorpt_coefficient_mu    3.256
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0955 before and 0.0672 after correction.
The Ratio of minimum to maximum transmission is 0.7897.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             718
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.083
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.999
_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       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            26902
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.638
_diffrn_ambient_temperature      300
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1974
_reflns_number_total             2238
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.380
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         2238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0271
_refine_ls_restrained_S_all      1.100
_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)+(0.0180P)²+2.3942P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0555
_refine_ls_wR_factor_ref         0.0583
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C3(H3)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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
Yb1 Yb 0.333333 0.666667 0.44545(3) 0.02505(8) Uani 1 3 d S T P . .
O1 O 0.25186(18) 0.52538(17) 0.5967(3) 0.0330(5) Uani 1 1 d . . . . .
N2 N 0.3908(2) 0.5523(2) 0.3271(4) 0.0319(6) Uani 1 1 d . . . . .
N1 N 0.333333 0.666667 0.1011(6) 0.0301(11) Uani 1 3 d S T P . .
C5 C 0.2601(2) 0.4436(2) 0.6375(4) 0.0288(7) Uani 1 1 d . . . . .
C6 C 0.1991(3) 0.3773(3) 0.7722(5) 0.0379(8) Uani 1 1 d . . . . .
H6 H 0.152944 0.392034 0.831037 0.045 Uiso 1 1 calc R U . . .
C7 C 0.2060(3) 0.2906(3) 0.8194(5) 0.0467(10) Uani 1 1 d . . . . .
H7 H 0.165311 0.248323 0.910000 0.056 Uiso 1 1 calc R U . . .
C8 C 0.2732(4) 0.2666(3) 0.7323(5) 0.0502(10) Uani 1 1 d . . . . .
O2 O 0.2832(3) 0.1814(3) 0.7842(5) 0.0798(11) Uani 1 1 d . . . . .
C10 C 0.2135(6) 0.0889(4) 0.7115(8) 0.096(2) Uani 1 1 d . . . . .
H10A H 0.219308 0.094733 0.587717 0.144 Uiso 1 1 calc R U . . .
H10B H 0.143992 0.070891 0.745716 0.144 Uiso 1 1 calc R U . . .
H10C H 0.227900 0.035467 0.749715 0.144 Uiso 1 1 calc R U . . .
C9 C 0.3321(3) 0.3274(3) 0.5973(5) 0.0448(9) Uani 1 1 d . . . . .
H9 H 0.375720 0.309552 0.537836 0.054 Uiso 1 1 calc R U . . .
C4 C 0.3274(3) 0.4166(3) 0.5471(5) 0.0345(8) Uani 1 1 d . . . . .
C3 C 0.3846(3) 0.4699(3) 0.3937(5) 0.0366(8) Uani 1 1 d . . . . .
H3 H 0.420636 0.441805 0.337370 0.044 Uiso 1 1 calc R U . . .
C1 C 0.4077(3) 0.7734(3) 0.0367(5) 0.0401(8) Uani 1 1 d . . . . .
H1A H 0.385876 0.783078 -0.076948 0.048 Uiso 1 1 calc R U . . .
H1B H 0.476903 0.781610 0.025944 0.048 Uiso 1 1 calc R U . . .
C2 C 0.4431(3) 0.5884(3) 0.1598(5) 0.0406(9) Uani 1 1 d . . . . .
H2A H 0.465051 0.540703 0.116690 0.049 Uiso 1 1 calc R U . . .
H2B H 0.504362 0.657274 0.171458 0.049 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Yb1 O1 2.157(2) 3_565 ?
Yb1 O1 2.157(2) 2_665 ?
Yb1 O1 2.157(2) . ?
Yb1 N2 2.416(3) 2_665 ?
Yb1 N2 2.416(3) . ?
Yb1 N2 2.416(3) 3_565 ?
Yb1 N1 2.659(4) . ?
O1 C5 1.311(4) . ?
N2 C3 1.282(4) . ?
N2 C2 1.462(4) . ?
N1 C1 1.485(4) 2_665 ?
N1 C1 1.485(4) 3_565 ?
N1 C1 1.485(4) . ?
C5 C6 1.403(5) . ?
C5 C4 1.426(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.384(6) . ?
C8 O2 1.397(5) . ?
C8 C9 1.367(6) . ?
O2 C10 1.354(7) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C9 H9 0.9300 . ?
C9 C4 1.407(5) . ?
C4 C3 1.439(5) . ?
C3 H3 0.9300 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.510(5) 2_665 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?

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 93.47(9) 3_565 2_665 ?
O1 Yb1 O1 93.47(9) 3_565 . ?
O1 Yb1 O1 93.47(9) 2_665 . ?
O1 Yb1 N2 75.52(9) 2_665 2_665 ?
O1 Yb1 N2 75.51(9) . . ?
O1 Yb1 N2 168.29(9) 3_565 . ?
O1 Yb1 N2 168.29(9) . 2_665 ?
O1 Yb1 N2 75.51(9) 3_565 3_565 ?
O1 Yb1 N2 83.40(9) 2_665 . ?
O1 Yb1 N2 168.29(9) 2_665 3_565 ?
O1 Yb1 N2 83.40(9) . 3_565 ?
O1 Yb1 N2 83.40(9) 3_565 2_665 ?
O1 Yb1 N1 122.77(6) 3_565 . ?
O1 Yb1 N1 122.77(6) 2_665 . ?
O1 Yb1 N1 122.77(6) . . ?
N2 Yb1 N2 106.58(7) 3_565 2_665 ?
N2 Yb1 N2 106.59(7) 2_665 . ?
N2 Yb1 N2 106.59(7) 3_565 . ?
N2 Yb1 N1 67.78(7) . . ?
N2 Yb1 N1 67.78(7) 3_565 . ?
N2 Yb1 N1 67.78(7) 2_665 . ?
C5 O1 Yb1 139.2(2) . . ?
C3 N2 Yb1 128.9(2) . . ?
C3 N2 C2 118.3(3) . . ?
C2 N2 Yb1 112.7(2) . . ?
C1 N1 Yb1 109.6(2) 2_665 . ?
C1 N1 Yb1 109.6(2) . . ?
C1 N1 Yb1 109.6(2) 3_565 . ?
C1 N1 C1 109.4(2) 2_665 3_565 ?
C1 N1 C1 109.4(2) . 3_565 ?
C1 N1 C1 109.4(2) 2_665 . ?
O1 C5 C6 119.9(3) . . ?
O1 C5 C4 122.6(3) . . ?
C6 C5 C4 117.5(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.5(4) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.2(4) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 O2 120.3(4) . . ?
C9 C8 C7 120.3(4) . . ?
C9 C8 O2 119.4(4) . . ?
C10 O2 C8 114.9(4) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C4 120.8(4) . . ?
C4 C9 H9 119.6 . . ?
C5 C4 C3 123.4(3) . . ?
C9 C4 C5 119.6(3) . . ?
C9 C4 C3 116.7(3) . . ?
N2 C3 C4 126.4(3) . . ?
N2 C3 H3 116.8 . . ?
C4 C3 H3 116.8 . . ?
N1 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
N1 C1 C2 110.3(3) . 2_665 ?
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.6 2_665 . ?
C2 C1 H1B 109.6 2_665 . ?
N2 C2 C1 107.4(3) . 3_565 ?
N2 C2 H2A 110.2 . . ?
N2 C2 H2B 110.2 . . ?
C1 C2 H2A 110.2 3_565 . ?
C1 C2 H2B 110.2 3_565 . ?
H2A C2 H2B 108.5 . . ?

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 C5 C6 166.9(2) . . . . ?
Yb1 O1 C5 C4 -14.7(5) . . . . ?
Yb1 N2 C3 C4 9.7(5) . . . . ?
Yb1 N2 C2 C1 -60.0(3) . . . 3_565 ?
Yb1 N1 C1 C2 -32.5(3) . . . 2_665 ?
O1 C5 C6 C7 -179.7(3) . . . . ?
O1 C5 C4 C9 -179.7(3) . . . . ?
O1 C5 C4 C3 -6.2(5) . . . . ?
C5 C6 C7 C8 -0.7(6) . . . . ?
C5 C4 C3 N2 6.6(6) . . . . ?
C6 C5 C4 C9 -1.3(5) . . . . ?
C6 C5 C4 C3 172.2(3) . . . . ?
C6 C7 C8 O2 177.6(4) . . . . ?
C6 C7 C8 C9 -1.0(6) . . . . ?
C7 C8 O2 C10 87.6(6) . . . . ?
C7 C8 C9 C4 1.6(6) . . . . ?
C8 C9 C4 C5 -0.4(6) . . . . ?
C8 C9 C4 C3 -174.4(4) . . . . ?
O2 C8 C9 C4 -177.0(4) . . . . ?
C9 C8 O2 C10 -93.8(6) . . . . ?
C9 C4 C3 N2 -179.7(4) . . . . ?
C4 C5 C6 C7 1.9(5) . . . . ?
C3 N2 C2 C1 122.5(3) . . . 3_565 ?
C1 N1 C1 C2 87.7(5) 2_665 . . 2_665 ?
C1 N1 C1 C2 -152.6(3) 3_565 . . 2_665 ?
C2 N2 C3 C4 -173.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_Ybtrenovan_300K
_database_code_depnum_ccdc_archive 'CCDC 2236956'
loop_
_audit_author_name
_audit_author_address
'Christian Dirk Buch'
;University of Copenhagen
Denmark
;
_audit_update_record             
;
2023-01-18 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_audit_creation_date             2023-01-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H33 N4 O6 Yb'
_chemical_formula_sum            'C30 H33 N4 O6 Yb'
_chemical_formula_weight         718.64
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Yb Yb -0.3850 5.5486 '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      trigonal
_space_group_IT_number           147
_space_group_name_H-M_alt        'P -3'
_space_group_name_Hall           '-P 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'

_cell_length_a                   13.9807(6)
_cell_length_b                   13.9807(6)
_cell_length_c                   8.3621(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1415.48(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    300
_cell_measurement_theta_max      30.407
_cell_measurement_theta_min      2.914
_shelx_estimated_absorpt_T_max   0.582
_shelx_estimated_absorpt_T_min   0.251
_exptl_absorpt_coefficient_mu    3.354
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1016 before and 0.0584 after correction.
The Ratio of minimum to maximum transmission is 0.5588.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             718
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.181
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            28917
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.026
_diffrn_reflns_theta_min         2.436
_diffrn_ambient_temperature      300
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2450
_reflns_number_total             2753
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.534
_refine_diff_density_min         -1.395
_refine_diff_density_rms         0.136
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.257
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         2753
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0246
_refine_ls_restrained_S_all      1.257
_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)+(0.0277P)²+0.2741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0597
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C9(H9)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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
Yb1 Yb 0.333333 0.666667 0.61172(2) 0.02930(7) Uani 1 3 d S T P . .
O1 O 0.47350(13) 0.68049(14) 0.7420(2) 0.0357(4) Uani 1 1 d . . . . .
O2 O 0.57371(15) 0.63415(17) 0.9728(2) 0.0468(4) Uani 1 1 d . . . . .
N2 N 0.49395(19) 0.81561(17) 0.4829(3) 0.0400(5) Uani 1 1 d . . . . .
N1 N 0.333333 0.666667 0.2671(5) 0.0492(10) Uani 1 3 d S T P . .
C2 C 0.4665(3) 0.8572(3) 0.3390(3) 0.0543(7) Uani 1 1 d . . . . .
H2A H 0.530245 0.925261 0.303361 0.065 Uiso 1 1 calc R U . . .
H2B H 0.406883 0.871720 0.361422 0.065 Uiso 1 1 calc R U . . .
C1 C 0.4318(3) 0.7696(3) 0.2121(3) 0.0617(8) Uani 1 1 d . . . . .
H1A H 0.414719 0.794879 0.113885 0.074 Uiso 1 1 calc R U . . .
H1B H 0.491790 0.755408 0.190448 0.074 Uiso 1 1 calc R U . . .
C3 C 0.5972(2) 0.8571(2) 0.5134(3) 0.0407(5) Uani 1 1 d . . . . .
H3 H 0.646153 0.914139 0.447263 0.049 Uiso 1 1 calc R U . . .
C4 C 0.64497(19) 0.8243(2) 0.6394(3) 0.0365(5) Uani 1 1 d . . . . .
C5 C 0.58041(18) 0.73859(18) 0.7483(3) 0.0304(4) Uani 1 1 d . . . . .
C6 C 0.63884(19) 0.7171(2) 0.8706(3) 0.0356(5) Uani 1 1 d . . . . .
C7 C 0.7530(2) 0.7773(2) 0.8794(4) 0.0464(6) Uani 1 1 d . . . . .
H7 H 0.789352 0.762213 0.960063 0.056 Uiso 1 1 calc R U . . .
C8 C 0.8138(2) 0.8602(3) 0.7686(4) 0.0554(8) Uani 1 1 d . . . . .
H8 H 0.890503 0.899308 0.774557 0.066 Uiso 1 1 calc R U . . .
C9 C 0.7616(2) 0.8840(2) 0.6524(4) 0.0491(7) Uani 1 1 d . . . . .
H9 H 0.802908 0.940377 0.580062 0.059 Uiso 1 1 calc R U . . .
C10 C 0.6276(3) 0.6106(3) 1.0984(4) 0.0565(8) Uani 1 1 d . . . . .
H10A H 0.683783 0.598126 1.054162 0.085 Uiso 1 1 calc R U . . .
H10B H 0.574559 0.545684 1.154774 0.085 Uiso 1 1 calc R U . . .
H10C H 0.660630 0.671926 1.170983 0.085 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 2.1644(16) 2_665 ?
Yb1 O1 2.1644(16) 3_565 ?
Yb1 O1 2.1644(16) . ?
Yb1 N2 2.421(2) 3_565 ?
Yb1 N2 2.421(2) 2_665 ?
Yb1 N2 2.421(2) . ?
Yb1 N1 2.882(4) . ?
O1 C5 1.297(3) . ?
O2 C6 1.360(3) . ?
O2 C10 1.424(3) . ?
N2 C2 1.469(3) . ?
N2 C3 1.284(3) . ?
N1 C1 1.482(4) . ?
N1 C1 1.482(4) 2_665 ?
N1 C1 1.482(4) 3_565 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.505(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 H3 0.9300 . ?
C3 C4 1.439(4) . ?
C4 C5 1.414(3) . ?
C4 C9 1.417(3) . ?
C5 C6 1.431(3) . ?
C6 C7 1.385(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.393(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.353(4) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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 96.91(6) 2_665 3_565 ?
O1 Yb1 O1 96.91(6) 2_665 . ?
O1 Yb1 O1 96.91(6) 3_565 . ?
O1 Yb1 N2 74.82(7) . . ?
O1 Yb1 N2 86.84(7) 2_665 . ?
O1 Yb1 N2 86.84(7) 3_565 2_665 ?
O1 Yb1 N2 74.82(7) 2_665 2_665 ?
O1 Yb1 N2 171.32(7) 3_565 . ?
O1 Yb1 N2 171.32(7) . 2_665 ?
O1 Yb1 N2 86.84(7) . 3_565 ?
O1 Yb1 N2 171.32(7) 2_665 3_565 ?
O1 Yb1 N2 74.82(7) 3_565 3_565 ?
O1 Yb1 N1 120.21(5) 2_665 . ?
O1 Yb1 N1 120.21(5) . . ?
O1 Yb1 N1 120.21(5) 3_565 . ?
N2 Yb1 N2 101.72(7) 2_665 . ?
N2 Yb1 N2 101.72(7) . 3_565 ?
N2 Yb1 N2 101.72(7) 2_665 3_565 ?
N2 Yb1 N1 63.59(5) . . ?
N2 Yb1 N1 63.59(5) 3_565 . ?
N2 Yb1 N1 63.59(5) 2_665 . ?
C5 O1 Yb1 141.72(15) . . ?
C6 O2 C10 117.1(2) . . ?
C2 N2 Yb1 113.04(18) . . ?
C3 N2 Yb1 130.53(17) . . ?
C3 N2 C2 116.2(2) . . ?
C1 N1 Yb1 108.08(19) 3_565 . ?
C1 N1 Yb1 108.08(19) 2_665 . ?
C1 N1 Yb1 108.08(19) . . ?
C1 N1 C1 110.83(18) . 3_565 ?
C1 N1 C1 110.83(18) 2_665 3_565 ?
C1 N1 C1 110.83(18) 2_665 . ?
N2 C2 H2A 110.3 . . ?
N2 C2 H2B 110.3 . . ?
N2 C2 C1 107.3(2) . . ?
H2A C2 H2B 108.5 . . ?
C1 C2 H2A 110.3 . . ?
C1 C2 H2B 110.3 . . ?
N1 C1 C2 109.6(3) . . ?
N1 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
C2 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
N2 C3 H3 116.6 . . ?
N2 C3 C4 126.7(2) . . ?
C4 C3 H3 116.6 . . ?
C5 C4 C3 122.7(2) . . ?
C5 C4 C9 120.6(2) . . ?
C9 C4 C3 116.7(2) . . ?
O1 C5 C4 123.5(2) . . ?
O1 C5 C6 119.9(2) . . ?
C4 C5 C6 116.7(2) . . ?
O2 C6 C5 114.8(2) . . ?
O2 C6 C7 124.2(2) . . ?
C7 C6 C5 121.0(2) . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 H9 119.5 . . ?
C8 C9 C4 120.9(3) . . ?
C8 C9 H9 119.5 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Yb1 O1 C5 C4 -3.7(4) . . . . ?
Yb1 O1 C5 C6 176.31(17) . . . . ?
Yb1 N2 C2 C1 -71.0(3) . . . . ?
Yb1 N2 C3 C4 -0.9(4) . . . . ?
Yb1 N1 C1 C2 -25.4(3) . . . . ?
O1 C5 C6 O2 0.0(3) . . . . ?
O1 C5 C6 C7 179.5(2) . . . . ?
O2 C6 C7 C8 179.2(3) . . . . ?
N2 C2 C1 N1 60.8(3) . . . . ?
N2 C3 C4 C5 0.2(4) . . . . ?
N2 C3 C4 C9 -178.5(3) . . . . ?
C2 N2 C3 C4 -175.0(3) . . . . ?
C1 N1 C1 C2 92.9(4) 2_665 . . . ?
C1 N1 C1 C2 -143.6(3) 3_565 . . . ?
C3 N2 C2 C1 104.0(3) . . . . ?
C3 C4 C5 O1 1.8(4) . . . . ?
C3 C4 C5 C6 -178.1(2) . . . . ?
C3 C4 C9 C8 179.0(3) . . . . ?
C4 C5 C6 O2 180.0(2) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C5 C4 C9 C8 0.3(4) . . . . ?
C5 C6 C7 C8 -0.2(4) . . . . ?
C6 C7 C8 C9 1.1(4) . . . . ?
C7 C8 C9 C4 -1.1(5) . . . . ?
C9 C4 C5 O1 -179.5(2) . . . . ?
C9 C4 C5 C6 0.5(3) . . . . ?
C10 O2 C6 C5 -179.0(2) . . . . ?
C10 O2 C6 C7 1.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
