# Electronic Supplementary Material (ESI) for Organic 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_exp_196_tpdpp_sublimation_auto
_database_code_depnum_ccdc_archive 'CCDC 2352552'
loop_
_audit_author_name
_audit_author_address
'Kazuo Takimiya'
;RIKEN
Japan
;
_audit_update_record             
;
2024-05-02 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;
_audit_creation_date             2022-06-09
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        C40H28O2
_chemical_formula_moiety         'C40 H28 O2'
_chemical_formula_sum            'C40 H28 O2'
_chemical_formula_weight         540.62
_chemical_melting_point          ?
_chemical_oxdiff_formula         C40H28O2
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   17.0901(7)
_cell_length_b                   5.7243(2)
_cell_length_c                   29.7971(11)
_cell_angle_alpha                90
_cell_angle_beta                 104.114(4)
_cell_angle_gamma                90
_cell_volume                     2827.04(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    955
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.2970
_cell_measurement_theta_min      3.1140
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.116a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark blue'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            12629
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.639
_diffrn_reflns_theta_min         2.458
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'Rigaku HyPix-3000 area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  12.50   0.50  338.73    --   20.00  54.00 -30.00   51
  2  ω     33.00  61.50   0.50  338.73    --   20.00  54.00 -30.00   57
  3  ω     85.00 109.50   0.50  338.73    --   20.00  54.00 -30.00   49
  4  ω    -73.00 109.50   0.50  338.73    --   20.00  54.00  30.00  365
  5  ω      5.00  62.50   0.50  338.73    --   20.00  54.00 -90.00  115
  6  ω    -74.00 -13.50   0.50  338.73    --   20.00  54.00-180.00  121
  7  ω     83.00 107.50   0.50  338.73    --   20.00  54.00-180.00   49
  8  ω    -60.00 -30.50   0.50  338.73    --   20.00  54.00-120.00   59
  9  ω     67.00  91.50   0.50  338.73    --   20.00  54.00-120.00   49
 10  ω    -53.00 -28.50   0.50  338.73    --   20.00  54.00-150.00   49
 11  ω     45.00  69.50   0.50  338.73    --   20.00  54.00-150.00   49
 12  ω    -46.00 -21.50   0.50  338.73    --   20.00  54.00 -30.00   49
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0115060000
_diffrn_orient_matrix_UB_12      -0.0881507000
_diffrn_orient_matrix_UB_13      -0.0170785000
_diffrn_orient_matrix_UB_21      0.0410715000
_diffrn_orient_matrix_UB_22      -0.0172261000
_diffrn_orient_matrix_UB_23      -0.0000779000
_diffrn_orient_matrix_UB_31      0.0035831000
_diffrn_orient_matrix_UB_32      -0.0852985000
_diffrn_orient_matrix_UB_33      0.0176369000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2568
_reflns_number_total             4158
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0619
_refine_ls_restrained_S_all      1.053
_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)+(0.0487P)²+1.0037P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1403
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C21(H21), C12(H12), C18(H18), C11(H11), C8(H8), C14(H14),
 C16(H16), C10(H10), C17(H17), C9(H9), C15(H15), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O6 O 0.31672(6) 0.03174(18) 0.13603(3) 0.0493(3) Uani 1 1 d . . . . .
C2 C 0.41907(9) -0.1459(3) 0.10624(5) 0.0461(4) Uani 1 1 d . . . . .
H2 H 0.458214 -0.261351 0.108950 0.055 Uiso 1 1 calc R U . . .
C7 C 0.38312(8) -0.2888(3) 0.17859(5) 0.0420(3) Uani 1 1 d . . . . .
C19 C 0.45295(9) 0.0073(3) 0.03448(5) 0.0441(4) Uani 1 1 d . . . . .
C4 C 0.34566(9) 0.1861(3) 0.06800(5) 0.0500(4) Uani 1 1 d . . . . .
H4 H 0.334778 0.297378 0.044550 0.060 Uiso 1 1 calc R U . . .
C3 C 0.40743(9) 0.0148(3) 0.06791(5) 0.0445(4) Uani 1 1 d . . . . .
C21 C 0.44728(9) 0.1833(3) -0.00036(5) 0.0481(4) Uani 1 1 d . . . . .
H21 H 0.411937 0.307431 -0.000892 0.058 Uiso 1 1 calc R U . . .
C1 C 0.37572(8) -0.1355(3) 0.13818(5) 0.0426(3) Uani 1 1 d . . . . .
C5 C 0.30316(9) 0.1925(3) 0.10034(5) 0.0451(4) Uani 1 1 d . . . . .
C13 C 0.23939(9) 0.3598(3) 0.10373(5) 0.0470(4) Uani 1 1 d . . . . .
C12 C 0.42740(9) -0.4967(3) 0.18282(5) 0.0474(4) Uani 1 1 d . . . . .
H12 H 0.452625 -0.539034 0.159680 0.057 Uiso 1 1 calc R U . . .
C18 C 0.22015(10) 0.5488(3) 0.07339(6) 0.0565(4) Uani 1 1 d . . . . .
H18 H 0.247590 0.568579 0.050269 0.068 Uiso 1 1 calc R U . . .
C11 C 0.43414(10) -0.6395(3) 0.22073(6) 0.0566(4) Uani 1 1 d . . . . .
H11 H 0.464342 -0.776089 0.223136 0.068 Uiso 1 1 calc R U . . .
C8 C 0.34587(10) -0.2318(3) 0.21382(6) 0.0540(4) Uani 1 1 d . . . . .
H8 H 0.316222 -0.094324 0.211904 0.065 Uiso 1 1 calc R U . . .
C14 C 0.19740(10) 0.3374(3) 0.13791(6) 0.0598(4) Uani 1 1 d . . . . .
H14 H 0.208756 0.213091 0.158573 0.072 Uiso 1 1 calc R U . . .
C16 C 0.12060(11) 0.6830(3) 0.11149(7) 0.0686(5) Uani 1 1 d . . . . .
H16 H 0.081384 0.790965 0.114255 0.082 Uiso 1 1 calc R U . . .
C10 C 0.39651(11) -0.5817(3) 0.25511(6) 0.0657(5) Uani 1 1 d . . . . .
H10 H 0.400713 -0.679554 0.280494 0.079 Uiso 1 1 calc R U . . .
C17 C 0.16103(11) 0.7066(3) 0.07720(7) 0.0656(5) Uani 1 1 d . . . . .
H17 H 0.148495 0.829981 0.056366 0.079 Uiso 1 1 calc R U . . .
C9 C 0.35248(11) -0.3774(4) 0.25169(6) 0.0661(5) Uani 1 1 d . . . . .
H9 H 0.327148 -0.337430 0.274914 0.079 Uiso 1 1 calc R U . . .
C15 C 0.13856(11) 0.4988(3) 0.14161(7) 0.0689(5) Uani 1 1 d . . . . .
H15 H 0.111077 0.481632 0.164779 0.083 Uiso 1 1 calc R U . . .
C20 C 0.49107(9) 0.1769(3) -0.03248(5) 0.0485(4) Uani 1 1 d . . . . .
H20 H 0.484647 0.296639 -0.054166 0.058 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
O6 C1 1.3807(17) . ?
O6 C5 1.3824(17) . ?
C2 C3 1.442(2) . ?
C2 C1 1.342(2) . ?
C7 C1 1.470(2) . ?
C7 C12 1.400(2) . ?
C7 C8 1.393(2) . ?
C19 C3 1.406(2) . ?
C19 C21 1.433(2) . ?
C19 C20 1.435(2) 5_655 ?
C4 C3 1.441(2) . ?
C4 C5 1.341(2) . ?
C21 C20 1.352(2) . ?
C5 C13 1.473(2) . ?
C13 C18 1.397(2) . ?
C13 C14 1.388(2) . ?
C12 C11 1.376(2) . ?
C18 C17 1.381(2) . ?
C11 C10 1.376(2) . ?
C8 C9 1.385(2) . ?
C14 C15 1.390(2) . ?
C16 C17 1.373(3) . ?
C16 C15 1.370(3) . ?
C10 C9 1.381(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
C1 O6 C5 118.73(11) . . ?
C1 C2 C3 122.70(14) . . ?
C12 C7 C1 121.18(14) . . ?
C8 C7 C1 120.92(14) . . ?
C8 C7 C12 117.90(14) . . ?
C3 C19 C21 122.71(14) . . ?
C3 C19 C20 122.80(13) . 5_655 ?
C21 C19 C20 114.49(13) . 5_655 ?
C5 C4 C3 123.01(14) . . ?
C19 C3 C2 123.26(14) . . ?
C19 C3 C4 123.64(13) . . ?
C4 C3 C2 113.09(13) . . ?
C20 C21 C19 122.85(14) . . ?
O6 C1 C7 111.57(12) . . ?
C2 C1 O6 121.38(13) . . ?
C2 C1 C7 127.04(14) . . ?
O6 C5 C13 111.59(13) . . ?
C4 C5 O6 121.08(14) . . ?
C4 C5 C13 127.33(14) . . ?
C18 C13 C5 121.37(15) . . ?
C14 C13 C5 120.95(14) . . ?
C14 C13 C18 117.67(15) . . ?
C11 C12 C7 120.94(15) . . ?
C17 C18 C13 121.01(17) . . ?
C12 C11 C10 120.49(16) . . ?
C9 C8 C7 120.76(16) . . ?
C13 C14 C15 120.71(17) . . ?
C15 C16 C17 119.38(17) . . ?
C11 C10 C9 119.61(16) . . ?
C16 C17 C18 120.53(17) . . ?
C10 C9 C8 120.30(17) . . ?
C16 C15 C14 120.70(18) . . ?
C21 C20 C19 122.66(13) . 5_655 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.071
_oxdiff_exptl_absorpt_empirical_full_min 0.913
####################################################################### 
# 
# 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_231030_matsuo_tpdp_1_2-3
_database_code_depnum_ccdc_archive 'CCDC 2352553'
loop_
_audit_author_name
_audit_author_address
'Kazuo Takimiya'
;RIKEN
Japan
;
_audit_update_record             
;
2024-05-02 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;
_audit_creation_date             2024-04-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C48 H48 N4 O2'
_chemical_formula_sum            'C48 H48 N4 O2'
_chemical_formula_weight         712.90
_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 0.0181 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'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.38540(10)
_cell_length_b                   7.76280(10)
_cell_length_c                   37.5449(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.4940(10)
_cell_angle_gamma                90
_cell_volume                     1860.98(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8475
_cell_measurement_temperature    100
_cell_measurement_theta_max      73.0440
_cell_measurement_theta_min      2.3600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.94a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            17723
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.044
_diffrn_reflns_theta_min         2.354
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  79.00   0.50    4.00    --   41.55 -95.00 -48.00  216
  2  ω   -169.00 -88.00   0.50   16.00    --  -97.00-114.00-132.00  162
  3  ω   -174.00 -73.00   0.50   16.00    --  -97.00 -31.00  78.00  202
  4  ω   -169.00 -88.00   0.50   16.00    --  -97.00-114.00-132.00  162
  5  ω     20.00 115.00   0.50    4.00    --   41.55  57.00  60.00  190
  6  ω    -38.00  24.00   0.50    4.00    --   41.55 -19.00-180.00  124
  7  ω    -74.00 -23.00   0.50   16.00    --  -97.00  61.00  60.00  102
  8  ω    -53.00 -21.00   0.50   16.00    --  -97.00  45.00-120.00   64
  9  ω   -105.00 -22.00   0.50   16.00    --  -97.00  95.00  61.00  166
 10  ω     35.00 102.00   0.50   16.00    --  106.13-125.00 -30.00  134
 11  ω     35.00 102.00   0.50   16.00    --  106.13-125.00 -30.00  134
 12  ω     38.00  65.00   0.50   16.00    --  106.13 -61.00-150.00   54
 13  ω   -122.00 -94.00   0.50   16.00    --  -97.00 -95.00 -48.00   56
 14  ω    -53.00 -28.00   0.50   16.00    --  -97.00  45.00  90.00   50
 15  ω    -53.00 -21.00   0.50   16.00    --  -97.00  45.00  60.00   64
 16  ω     33.00  64.00   0.50   16.00    --  106.13 -61.00 150.00   62
 17  ω     32.00  61.00   0.50   16.00    --  106.13 -61.00 -60.00   58
 18  ω     32.00  58.00   0.50   16.00    --  106.13 -61.00 -30.00   52
 19  ω     47.00  73.00   0.50   16.00    --  106.13 -94.00-180.00   52
 20  ω     80.00 105.00   0.50   16.00    --  106.13 -94.00 -30.00   50
 21  ω     32.00  57.00   0.50   16.00    --  106.13 -61.00-120.00   50
 22  ω    -38.00  24.00   0.50    6.72    --   41.55 -19.00 120.00  124
 23  ω     20.00 115.00   0.50    6.72    --   41.55  57.00 150.00  190
 24  ω     20.00 115.00   0.50    6.72    --   41.55  57.00 -60.00  190
 25  ω     13.00 115.00   0.50    6.72    --   41.55  77.00-180.00  204
 26  ω   -171.00 -97.00   0.50   16.00    --  -97.00 -77.00  60.00  148
 27  ω   -171.00 -68.00   0.50   16.00    --  -97.00 -77.00 -30.00  206
 28  ω   -174.00 -47.00   0.50   16.00    --  -97.00 -15.00-180.00  254
 29  ω   -171.00 -68.00   0.50   16.00    --  -97.00 -77.00   0.00  206
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2943
_reflns_number_total             3513
_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 1.171.43.94a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.92a 64-bit (release 05-10-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.94a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3513
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.051
_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)+(0.0666P)²+1.0719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1392
_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:
 C005(H005), C00A(H00A), C00B(H00B), C00D(H00D), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00K(H00K), C00M(H00M), C00N(H00N), C00P(H00Q)
2.b Idealised Me refined as rotating group:
 C00J(H00C,H00E,H00J), C00O(H00L,H00O,H00P), C00Q(H00R,H00S,H00T), C00R(H00U,
 H00V,H00W)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O001 O 0.42611(18) 0.73035(17) 0.37943(3) 0.0295(3) Uani 1 1 d . . . . .
N002 N 1.2628(2) 0.3255(2) 0.41600(4) 0.0324(4) Uani 1 1 d . . . . .
N003 N -0.0648(2) 0.7613(2) 0.23245(4) 0.0366(4) Uani 1 1 d . . . . .
C004 C 0.1103(2) 0.9373(2) 0.46883(4) 0.0254(4) Uani 1 1 d . . . . .
C005 C 0.1356(3) 0.8839(2) 0.40332(4) 0.0264(4) Uani 1 1 d . . . . .
H005 H 0.005597 0.940432 0.399298 0.032 Uiso 1 1 calc R U . . .
C006 C 0.7056(2) 0.6172(2) 0.41367(4) 0.0263(4) Uani 1 1 d . . . . .
C007 C 0.2361(2) 0.8147(2) 0.37524(4) 0.0263(4) Uani 1 1 d . . . . .
C008 C 0.2172(2) 0.8753(2) 0.43888(4) 0.0255(4) Uani 1 1 d . . . . .
C009 C 0.5118(3) 0.7179(2) 0.41324(4) 0.0262(4) Uani 1 1 d . . . . .
C00A C 0.7906(3) 0.5484(2) 0.38249(4) 0.0277(4) Uani 1 1 d . . . . .
H00A H 0.722061 0.569526 0.360368 0.033 Uiso 1 1 calc R U . . .
C00B C 0.4165(3) 0.7885(2) 0.44159(4) 0.0264(4) Uani 1 1 d . . . . .
H00B H 0.483097 0.780914 0.464259 0.032 Uiso 1 1 calc R U . . .
C00C C 1.0794(3) 0.4168(2) 0.41510(5) 0.0272(4) Uani 1 1 d . . . . .
C00D C 0.9712(3) 0.4507(2) 0.38301(4) 0.0279(4) Uani 1 1 d . . . . .
H00D H 1.023451 0.405506 0.361316 0.034 Uiso 1 1 calc R U . . .
C00E C 0.1646(3) 0.8095(2) 0.33819(4) 0.0273(4) Uani 1 1 d . . . . .
C00F C 0.0924(3) 0.9837(2) 0.53339(5) 0.0288(4) Uani 1 1 d . . . . .
H00F H 0.157348 0.971234 0.556101 0.035 Uiso 1 1 calc R U . . .
C00G C 0.9912(3) 0.4831(2) 0.44665(5) 0.0281(4) Uani 1 1 d . . . . .
H00G H 1.057432 0.460136 0.468900 0.034 Uiso 1 1 calc R U . . .
C00H C 0.8118(3) 0.5800(2) 0.44570(4) 0.0281(4) Uani 1 1 d . . . . .
H00H H 0.757556 0.623511 0.467392 0.034 Uiso 1 1 calc R U . . .
C00I C 0.1946(3) 0.9261(2) 0.50421(4) 0.0287(4) Uani 1 1 d . . . . .
H00I H 0.329035 0.875686 0.507408 0.034 Uiso 1 1 calc R U . . .
C00J C 1.3583(3) 0.2716(3) 0.38294(5) 0.0312(4) Uani 1 1 d . . . . .
H00C H 1.262054 0.195204 0.369991 0.047 Uiso 1 1 calc R U . . .
H00E H 1.488968 0.210035 0.388162 0.047 Uiso 1 1 calc R U . . .
H00J H 1.388328 0.373055 0.368322 0.047 Uiso 1 1 calc R U . . .
C00K C 0.2711(3) 0.7135(3) 0.31250(5) 0.0314(4) Uani 1 1 d . . . . .
H00K H 0.396586 0.655784 0.319184 0.038 Uiso 1 1 calc R U . . .
C00L C 0.0142(3) 0.7825(2) 0.26653(5) 0.0306(4) Uani 1 1 d . . . . .
C00M C 0.2002(3) 0.6998(3) 0.27785(5) 0.0330(4) Uani 1 1 d . . . . .
H00M H 0.277857 0.633608 0.261277 0.040 Uiso 1 1 calc R U . . .
C00N C -0.0165(3) 0.8955(3) 0.32660(5) 0.0335(4) Uani 1 1 d . . . . .
H00N H -0.091416 0.964252 0.343086 0.040 Uiso 1 1 calc R U . . .
C00O C 1.3792(3) 0.3063(3) 0.44905(5) 0.0318(4) Uani 1 1 d . . . . .
H00L H 1.408779 0.420267 0.459134 0.048 Uiso 1 1 calc R U . . .
H00O H 1.511373 0.246430 0.444434 0.048 Uiso 1 1 calc R U . . .
H00P H 1.296308 0.239160 0.465955 0.048 Uiso 1 1 calc R U . . .
C00P C -0.0893(3) 0.8834(3) 0.29201(5) 0.0346(4) Uani 1 1 d . . . . .
H00Q H -0.212119 0.944638 0.285242 0.042 Uiso 1 1 calc R U . . .
C00Q C -0.2348(3) 0.8716(3) 0.22026(5) 0.0419(5) Uani 1 1 d . . . . .
H00R H -0.356636 0.855289 0.235585 0.063 Uiso 1 1 calc R U . . .
H00S H -0.272393 0.841666 0.195663 0.063 Uiso 1 1 calc R U . . .
H00T H -0.189959 0.992262 0.221294 0.063 Uiso 1 1 calc R U . . .
C00R C 0.0667(3) 0.6844(3) 0.20546(5) 0.0402(5) Uani 1 1 d . . . . .
H00U H 0.188442 0.758389 0.201344 0.060 Uiso 1 1 calc R U . . .
H00V H -0.013586 0.671975 0.183240 0.060 Uiso 1 1 calc R U . . .
H00W H 0.114100 0.570730 0.213545 0.060 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
O001 C007 1.386(2) . ?
O001 C009 1.381(2) . ?
N002 C00C 1.369(2) . ?
N002 C00J 1.449(2) . ?
N002 C00O 1.449(2) . ?
N003 C00L 1.381(2) . ?
N003 C00Q 1.453(3) . ?
N003 C00R 1.451(2) . ?
C004 C008 1.405(2) . ?
C004 C00F 1.434(2) 3_576 ?
C004 C00I 1.431(2) . ?
C005 H005 0.9500 . ?
C005 C007 1.350(2) . ?
C005 C008 1.431(2) . ?
C006 C009 1.464(2) . ?
C006 C00A 1.400(2) . ?
C006 C00H 1.406(2) . ?
C007 C00E 1.461(2) . ?
C008 C00B 1.442(2) . ?
C009 C00B 1.347(2) . ?
C00A H00A 0.9500 . ?
C00A C00D 1.380(2) . ?
C00B H00B 0.9500 . ?
C00C C00D 1.409(2) . ?
C00C C00G 1.413(2) . ?
C00D H00D 0.9500 . ?
C00E C00K 1.400(2) . ?
C00E C00N 1.401(3) . ?
C00F H00F 0.9500 . ?
C00F C00I 1.356(2) . ?
C00G H00G 0.9500 . ?
C00G C00H 1.371(2) . ?
C00H H00H 0.9500 . ?
C00I H00I 0.9500 . ?
C00J H00C 0.9800 . ?
C00J H00E 0.9800 . ?
C00J H00J 0.9800 . ?
C00K H00K 0.9500 . ?
C00K C00M 1.378(2) . ?
C00L C00M 1.412(3) . ?
C00L C00P 1.406(3) . ?
C00M H00M 0.9500 . ?
C00N H00N 0.9500 . ?
C00N C00P 1.379(2) . ?
C00O H00L 0.9800 . ?
C00O H00O 0.9800 . ?
C00O H00P 0.9800 . ?
C00P H00Q 0.9500 . ?
C00Q H00R 0.9800 . ?
C00Q H00S 0.9800 . ?
C00Q H00T 0.9800 . ?
C00R H00U 0.9800 . ?
C00R H00V 0.9800 . ?
C00R H00W 0.9800 . ?

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
C009 O001 C007 118.47(13) . . ?
C00C N002 C00J 119.63(14) . . ?
C00C N002 C00O 120.46(14) . . ?
C00O N002 C00J 119.17(14) . . ?
C00L N003 C00Q 119.21(16) . . ?
C00L N003 C00R 119.14(15) . . ?
C00R N003 C00Q 117.25(15) . . ?
C008 C004 C00F 122.98(15) . 3_576 ?
C008 C004 C00I 122.71(15) . . ?
C00I C004 C00F 114.31(15) . 3_576 ?
C007 C005 H005 118.7 . . ?
C007 C005 C008 122.57(16) . . ?
C008 C005 H005 118.7 . . ?
C00A C006 C009 121.91(15) . . ?
C00A C006 C00H 116.67(15) . . ?
C00H C006 C009 121.38(15) . . ?
O001 C007 C00E 111.16(14) . . ?
C005 C007 O001 121.38(15) . . ?
C005 C007 C00E 127.42(15) . . ?
C004 C008 C005 123.74(15) . . ?
C004 C008 C00B 122.51(15) . . ?
C005 C008 C00B 113.68(15) . . ?
O001 C009 C006 112.06(14) . . ?
C00B C009 O001 121.29(15) . . ?
C00B C009 C006 126.62(16) . . ?
C006 C00A H00A 119.1 . . ?
C00D C00A C006 121.87(16) . . ?
C00D C00A H00A 119.1 . . ?
C008 C00B H00B 118.7 . . ?
C009 C00B C008 122.59(16) . . ?
C009 C00B H00B 118.7 . . ?
N002 C00C C00D 122.08(15) . . ?
N002 C00C C00G 120.98(16) . . ?
C00D C00C C00G 116.93(15) . . ?
C00A C00D C00C 121.21(15) . . ?
C00A C00D H00D 119.4 . . ?
C00C C00D H00D 119.4 . . ?
C00K C00E C007 121.41(16) . . ?
C00K C00E C00N 116.36(16) . . ?
C00N C00E C007 122.20(16) . . ?
C004 C00F H00F 118.8 3_576 . ?
C00I C00F C004 122.32(16) . 3_576 ?
C00I C00F H00F 118.8 . . ?
C00C C00G H00G 119.4 . . ?
C00H C00G C00C 121.13(16) . . ?
C00H C00G H00G 119.4 . . ?
C006 C00H H00H 118.9 . . ?
C00G C00H C006 122.15(16) . . ?
C00G C00H H00H 118.9 . . ?
C004 C00I H00I 118.3 . . ?
C00F C00I C004 123.37(16) . . ?
C00F C00I H00I 118.3 . . ?
N002 C00J H00C 109.5 . . ?
N002 C00J H00E 109.5 . . ?
N002 C00J H00J 109.5 . . ?
H00C C00J H00E 109.5 . . ?
H00C C00J H00J 109.5 . . ?
H00E C00J H00J 109.5 . . ?
C00E C00K H00K 118.9 . . ?
C00M C00K C00E 122.28(16) . . ?
C00M C00K H00K 118.9 . . ?
N003 C00L C00M 121.65(16) . . ?
N003 C00L C00P 121.75(16) . . ?
C00P C00L C00M 116.57(16) . . ?
C00K C00M C00L 121.19(17) . . ?
C00K C00M H00M 119.4 . . ?
C00L C00M H00M 119.4 . . ?
C00E C00N H00N 119.0 . . ?
C00P C00N C00E 122.06(17) . . ?
C00P C00N H00N 119.0 . . ?
N002 C00O H00L 109.5 . . ?
N002 C00O H00O 109.5 . . ?
N002 C00O H00P 109.5 . . ?
H00L C00O H00O 109.5 . . ?
H00L C00O H00P 109.5 . . ?
H00O C00O H00P 109.5 . . ?
C00L C00P H00Q 119.3 . . ?
C00N C00P C00L 121.48(17) . . ?
C00N C00P H00Q 119.3 . . ?
N003 C00Q H00R 109.5 . . ?
N003 C00Q H00S 109.5 . . ?
N003 C00Q H00T 109.5 . . ?
H00R C00Q H00S 109.5 . . ?
H00R C00Q H00T 109.5 . . ?
H00S C00Q H00T 109.5 . . ?
N003 C00R H00U 109.5 . . ?
N003 C00R H00V 109.5 . . ?
N003 C00R H00W 109.5 . . ?
H00U C00R H00V 109.5 . . ?
H00U C00R H00W 109.5 . . ?
H00V C00R H00W 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
O001 C007 C00E C00K 6.2(2) . . . . ?
O001 C007 C00E C00N -175.67(17) . . . . ?
O001 C009 C00B C008 2.4(3) . . . . ?
N002 C00C C00D C00A -177.56(17) . . . . ?
N002 C00C C00G C00H 177.51(17) . . . . ?
N003 C00L C00M C00K -176.10(18) . . . . ?
N003 C00L C00P C00N 175.97(19) . . . . ?
C004 C008 C00B C009 174.99(17) . . . . ?
C004 C00F C00I C004 -0.5(3) 3_576 . . . ?
C005 C007 C00E C00K -171.27(18) . . . . ?
C005 C007 C00E C00N 6.8(3) . . . . ?
C005 C008 C00B C009 -2.0(2) . . . . ?
C006 C009 C00B C008 -175.36(16) . . . . ?
C006 C00A C00D C00C -0.5(3) . . . . ?
C007 O001 C009 C006 176.72(14) . . . . ?
C007 O001 C009 C00B -1.3(2) . . . . ?
C007 C005 C008 C004 -176.18(17) . . . . ?
C007 C005 C008 C00B 0.8(2) . . . . ?
C007 C00E C00K C00M 176.59(17) . . . . ?
C007 C00E C00N C00P -176.71(18) . . . . ?
C008 C004 C00I C00F -179.30(18) . . . . ?
C008 C005 C007 O001 0.1(3) . . . . ?
C008 C005 C007 C00E 177.39(17) . . . . ?
C009 O001 C007 C005 0.1(2) . . . . ?
C009 O001 C007 C00E -177.61(14) . . . . ?
C009 C006 C00A C00D -178.75(16) . . . . ?
C009 C006 C00H C00G 178.70(17) . . . . ?
C00A C006 C009 O001 1.6(2) . . . . ?
C00A C006 C009 C00B 179.54(17) . . . . ?
C00A C006 C00H C00G 0.7(3) . . . . ?
C00C C00G C00H C006 0.6(3) . . . . ?
C00D C00C C00G C00H -1.8(3) . . . . ?
C00E C00K C00M C00L -0.2(3) . . . . ?
C00E C00N C00P C00L 0.5(3) . . . . ?
C00F C004 C008 C005 -0.2(3) 3_576 . . . ?
C00F C004 C008 C00B -176.94(16) 3_576 . . . ?
C00F C004 C00I C00F 0.5(3) 3_576 . . . ?
C00G C00C C00D C00A 1.7(3) . . . . ?
C00H C006 C009 O001 -176.21(15) . . . . ?
C00H C006 C009 C00B 1.7(3) . . . . ?
C00H C006 C00A C00D -0.8(3) . . . . ?
C00I C004 C008 C005 179.53(16) . . . . ?
C00I C004 C008 C00B 2.8(3) . . . . ?
C00J N002 C00C C00D 4.4(3) . . . . ?
C00J N002 C00C C00G -174.87(17) . . . . ?
C00K C00E C00N C00P 1.5(3) . . . . ?
C00M C00L C00P C00N -2.3(3) . . . . ?
C00N C00E C00K C00M -1.6(3) . . . . ?
C00O N002 C00C C00D 174.49(17) . . . . ?
C00O N002 C00C C00G -4.8(3) . . . . ?
C00P C00L C00M C00K 2.2(3) . . . . ?
C00Q N003 C00L C00M -169.38(18) . . . . ?
C00Q N003 C00L C00P 12.4(3) . . . . ?
C00R N003 C00L C00M -13.6(3) . . . . ?
C00R N003 C00L C00P 168.22(19) . . . . ?

_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
;
