# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_takeda_autored
_database_code_depnum_ccdc_archive 'CCDC 2423379'
loop_
_audit_author_name
_audit_author_address
'Norihiko Takeda'
;Kobe Pharmaceutical University
Japan
;
_audit_update_record             
;
2025-02-12 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H29 N O3'
_chemical_formula_weight         391.49

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6101(4)
_cell_length_b                   9.4347(6)
_cell_length_c                   15.4023(9)
_cell_angle_alpha                98.502(5)
_cell_angle_beta                 101.701(4)
_cell_angle_gamma                112.023(5)
_cell_volume                     1100.70(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21784
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.403
_diffrn_reflns_theta_max         27.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5326
_reflns_number_gt                3810
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0760P)²+1.0274P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5326
_refine_ls_number_parameters     268
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0759
_refine_ls_wR_factor_ref         0.1879
_refine_ls_wR_factor_gt          0.1721
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.56884(19) 0.40654(18) 0.60327(10) 0.0225(3) Uani 1 1 d . . . . .
H1 H 0.631048 0.415556 0.568711 0.034 Uiso 1 1 calc R U . . .
O3 O 0.6462(2) 0.4431(2) 0.44124(12) 0.0377(4) Uani 1 1 d . . . . .
H3A H 0.579354 0.480760 0.420401 0.057 Uiso 1 1 calc R U . . .
O2 O 0.7924(3) 0.1662(2) 0.79953(11) 0.0389(5) Uani 1 1 d . . . . .
N1 N 0.7327(2) 0.2839(2) 0.78773(13) 0.0248(4) Uani 1 1 d . . . . .
C15 C 0.8372(3) 0.6038(2) 0.71469(14) 0.0219(4) Uani 1 1 d . . . . .
C20 C 0.9962(3) 0.6324(3) 0.77520(15) 0.0257(5) Uani 1 1 d . . . . .
H20 H 1.006431 0.553793 0.802807 0.031 Uiso 1 1 calc R U . . .
C9 C 0.5591(3) 0.4614(3) 0.75885(15) 0.0244(5) Uani 1 1 d . . . . .
C1 C 0.7289(3) 0.3138(3) 0.70959(15) 0.0236(5) Uani 1 1 d . . . . .
C16 C 0.8257(3) 0.7228(3) 0.67415(16) 0.0265(5) Uani 1 1 d . . . . .
H16 H 0.721506 0.705599 0.632794 0.032 Uiso 1 1 calc R U . . .
C8 C 0.6744(3) 0.4485(2) 0.69605(14) 0.0224(4) Uani 1 1 d . . . . .
C2 C 0.7721(3) 0.2312(3) 0.63382(15) 0.0265(5) Uani 1 1 d . . . . .
C14 C 0.6241(3) 0.5749(3) 0.84119(16) 0.0276(5) Uani 1 1 d . . . . .
H14 H 0.741054 0.645919 0.859920 0.033 Uiso 1 1 calc R U . . .
C19 C 1.1388(3) 0.7758(3) 0.79475(16) 0.0286(5) Uani 1 1 d . . . . .
H19 H 1.244272 0.792911 0.834885 0.034 Uiso 1 1 calc R U . . .
C10 C 0.3835(3) 0.3545(3) 0.73308(17) 0.0304(5) Uani 1 1 d . . . . .
H10 H 0.338351 0.276405 0.678775 0.036 Uiso 1 1 calc R U . . .
C21 C 0.7866(3) 0.1377(3) 0.89036(16) 0.0314(5) Uani 1 1 d . U . . .
C3 C 0.6782(3) 0.0689(3) 0.60004(17) 0.0337(6) Uani 1 1 d . . . . .
H3 H 0.592287 0.013823 0.625712 0.040 Uiso 1 1 calc R U . . .
C17 C 0.9682(3) 0.8672(3) 0.69484(18) 0.0342(6) Uani 1 1 d . . . . .
H17 H 0.958214 0.946828 0.668195 0.041 Uiso 1 1 calc R U . . .
C7 C 0.9032(3) 0.3111(3) 0.59569(17) 0.0332(6) Uani 1 1 d . . . . .
H7 H 0.966343 0.419833 0.617089 0.040 Uiso 1 1 calc R U . . .
C18 C 1.1243(3) 0.8937(3) 0.75444(18) 0.0336(6) Uani 1 1 d . . . . .
H18 H 1.219786 0.990446 0.767621 0.040 Uiso 1 1 calc R U . . .
C11 C 0.2760(3) 0.3637(3) 0.78755(18) 0.0354(6) Uani 1 1 d . . . . .
H11 H 0.159147 0.292634 0.769483 0.043 Uiso 1 1 calc R U . . .
C13 C 0.5166(3) 0.5835(3) 0.89570(17) 0.0354(6) Uani 1 1 d . . . . .
H13 H 0.561556 0.660222 0.950606 0.043 Uiso 1 1 calc R U . . .
C4 C 0.7115(4) -0.0108(3) 0.52895(17) 0.0374(6) Uani 1 1 d . . . . .
H4 H 0.645376 -0.118740 0.505565 0.045 Uiso 1 1 calc R U . . .
C5 C 0.8422(3) 0.0683(3) 0.49214(17) 0.0365(6) Uani 1 1 d . . . . .
H5 H 0.864801 0.013523 0.444490 0.044 Uiso 1 1 calc R U . . .
C25 C 0.6552(4) 0.3364(3) 0.36923(18) 0.0374(6) Uani 1 1 d . . . . .
H25A H 0.693689 0.390659 0.324298 0.056 Uiso 1 1 calc R U . . .
H25B H 0.541770 0.251430 0.341323 0.056 Uiso 1 1 calc R U . . .
H25C H 0.736221 0.294798 0.393336 0.056 Uiso 1 1 calc R U . . .
C12 C 0.3428(4) 0.4784(3) 0.86866(18) 0.0385(6) Uani 1 1 d . . . . .
H12 H 0.270757 0.484903 0.905157 0.046 Uiso 1 1 calc R U . . .
C6 C 0.9397(4) 0.2290(3) 0.52600(18) 0.0388(6) Uani 1 1 d . . . . .
H6 H 1.029579 0.282071 0.502094 0.047 Uiso 1 1 calc R U . . .
C22 C 0.9108(5) 0.2809(4) 0.9617(2) 0.0587(9) Uani 1 1 d . U . . .
H22A H 1.025591 0.310389 0.953829 0.088 Uiso 1 1 calc R U . . .
H22B H 0.912026 0.260122 1.020964 0.088 Uiso 1 1 calc R U . . .
H22C H 0.875572 0.365294 0.956797 0.088 Uiso 1 1 calc R U . . .
C24 C 0.8536(7) 0.0091(5) 0.8912(3) 0.0852(13) Uani 1 1 d . U . . .
H24A H 0.783243 -0.077679 0.838845 0.128 Uiso 1 1 calc R U . . .
H24B H 0.846923 -0.026754 0.946028 0.128 Uiso 1 1 calc R U . . .
H24C H 0.972675 0.050907 0.889113 0.128 Uiso 1 1 calc R U . . .
C23 C 0.6063(5) 0.0829(6) 0.8961(3) 0.0925(15) Uani 1 1 d . U . . .
H23A H 0.566965 0.164841 0.891117 0.139 Uiso 1 1 calc R U . . .
H23B H 0.601637 0.057026 0.953814 0.139 Uiso 1 1 calc R U . . .
H23C H 0.532411 -0.008932 0.847293 0.139 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
O1 C8 1.436(2) . ?
O1 H1 0.8200 . ?
O3 C25 1.419(3) . ?
O3 H3A 0.8200 . ?
O2 N1 1.406(2) . ?
O2 C21 1.470(3) . ?
N1 C1 1.273(3) . ?
C15 C16 1.388(3) . ?
C15 C20 1.395(3) . ?
C15 C8 1.538(3) . ?
C20 C19 1.383(3) . ?
C20 H20 0.9300 . ?
C9 C14 1.389(3) . ?
C9 C10 1.398(3) . ?
C9 C8 1.543(3) . ?
C1 C2 1.494(3) . ?
C1 C8 1.538(3) . ?
C16 C17 1.387(3) . ?
C16 H16 0.9300 . ?
C2 C3 1.391(3) . ?
C2 C7 1.396(4) . ?
C14 C13 1.385(3) . ?
C14 H14 0.9300 . ?
C19 C18 1.384(3) . ?
C19 H19 0.9300 . ?
C10 C11 1.386(3) . ?
C10 H10 0.9300 . ?
C21 C23 1.467(4) . ?
C21 C22 1.476(4) . ?
C21 C24 1.527(4) . ?
C3 C4 1.375(4) . ?
C3 H3 0.9300 . ?
C17 C18 1.375(4) . ?
C17 H17 0.9300 . ?
C7 C6 1.387(3) . ?
C7 H7 0.9300 . ?
C18 H18 0.9300 . ?
C11 C12 1.380(4) . ?
C11 H11 0.9300 . ?
C13 C12 1.381(4) . ?
C13 H13 0.9300 . ?
C4 C5 1.378(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C12 H12 0.9300 . ?
C6 H6 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C8 O1 H1 109.5 . . ?
C25 O3 H3A 109.5 . . ?
N1 O2 C21 108.37(17) . . ?
C1 N1 O2 112.87(18) . . ?
C16 C15 C20 118.3(2) . . ?
C16 C15 C8 119.81(19) . . ?
C20 C15 C8 121.77(19) . . ?
C19 C20 C15 121.0(2) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
C14 C9 C10 118.4(2) . . ?
C14 C9 C8 122.3(2) . . ?
C10 C9 C8 119.3(2) . . ?
N1 C1 C2 125.9(2) . . ?
N1 C1 C8 114.44(19) . . ?
C2 C1 C8 119.62(18) . . ?
C17 C16 C15 120.5(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
O1 C8 C15 110.47(17) . . ?
O1 C8 C1 107.56(17) . . ?
C15 C8 C1 110.09(17) . . ?
O1 C8 C9 107.35(16) . . ?
C15 C8 C9 111.94(18) . . ?
C1 C8 C9 109.30(17) . . ?
C3 C2 C7 118.9(2) . . ?
C3 C2 C1 118.8(2) . . ?
C7 C2 C1 122.4(2) . . ?
C13 C14 C9 120.7(2) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C20 C19 C18 119.8(2) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C11 C10 C9 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C23 C21 O2 109.7(2) . . ?
C23 C21 C22 113.8(3) . . ?
O2 C21 C22 109.5(2) . . ?
C23 C21 C24 112.3(3) . . ?
O2 C21 C24 101.3(2) . . ?
C22 C21 C24 109.5(3) . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C18 C17 C16 120.5(2) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C6 C7 C2 120.2(2) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C17 C18 C19 119.8(2) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C12 C11 C10 119.9(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C11 C12 C13 120.1(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C5 C6 C7 119.9(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C21 O2 N1 C1 -178.30(19) . . . . ?
C16 C15 C20 C19 0.2(3) . . . . ?
C8 C15 C20 C19 -176.6(2) . . . . ?
O2 N1 C1 C2 3.1(3) . . . . ?
O2 N1 C1 C8 -176.65(17) . . . . ?
C20 C15 C16 C17 -1.1(3) . . . . ?
C8 C15 C16 C17 175.8(2) . . . . ?
C16 C15 C8 O1 36.1(3) . . . . ?
C20 C15 C8 O1 -147.1(2) . . . . ?
C16 C15 C8 C1 154.7(2) . . . . ?
C20 C15 C8 C1 -28.4(3) . . . . ?
C16 C15 C8 C9 -83.5(2) . . . . ?
C20 C15 C8 C9 93.4(2) . . . . ?
N1 C1 C8 O1 -142.53(19) . . . . ?
C2 C1 C8 O1 37.7(3) . . . . ?
N1 C1 C8 C15 97.1(2) . . . . ?
C2 C1 C8 C15 -82.7(2) . . . . ?
N1 C1 C8 C9 -26.3(3) . . . . ?
C2 C1 C8 C9 153.92(19) . . . . ?
C14 C9 C8 O1 -142.8(2) . . . . ?
C10 C9 C8 O1 37.9(3) . . . . ?
C14 C9 C8 C15 -21.5(3) . . . . ?
C10 C9 C8 C15 159.28(19) . . . . ?
C14 C9 C8 C1 100.8(2) . . . . ?
C10 C9 C8 C1 -78.5(2) . . . . ?
N1 C1 C2 C3 58.1(3) . . . . ?
C8 C1 C2 C3 -122.1(2) . . . . ?
N1 C1 C2 C7 -122.0(3) . . . . ?
C8 C1 C2 C7 57.8(3) . . . . ?
C10 C9 C14 C13 -1.0(3) . . . . ?
C8 C9 C14 C13 179.7(2) . . . . ?
C15 C20 C19 C18 0.5(4) . . . . ?
C14 C9 C10 C11 1.3(3) . . . . ?
C8 C9 C10 C11 -179.5(2) . . . . ?
N1 O2 C21 C23 60.9(3) . . . . ?
N1 O2 C21 C22 -64.7(3) . . . . ?
N1 O2 C21 C24 179.8(3) . . . . ?
C7 C2 C3 C4 -1.4(3) . . . . ?
C1 C2 C3 C4 178.5(2) . . . . ?
C15 C16 C17 C18 1.3(4) . . . . ?
C3 C2 C7 C6 -0.7(4) . . . . ?
C1 C2 C7 C6 179.4(2) . . . . ?
C16 C17 C18 C19 -0.6(4) . . . . ?
C20 C19 C18 C17 -0.3(4) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C9 C14 C13 C12 0.2(4) . . . . ?
C2 C3 C4 C5 2.1(4) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?
C14 C13 C12 C11 0.5(4) . . . . ?
C4 C5 C6 C7 -1.4(4) . . . . ?
C2 C7 C6 C5 2.1(4) . . . . ?

_refine_diff_density_max         0.598
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.057



####################################################################### 
# 
# 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_takeda_autored_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2423395'
loop_
_audit_author_name
_audit_author_address
'Norihiko Takeda'
;Kobe Pharmaceutical University
Japan
;
_audit_update_record             
;
2025-02-12 deposited with the CCDC.	2025-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 Br N O'
_chemical_formula_weight         420.33

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.5551(4)
_cell_length_b                   6.0134(3)
_cell_length_c                   19.1446(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.893(4)
_cell_angle_gamma                90
_cell_volume                     981.31(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.108
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19448
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.135
_diffrn_reflns_theta_max         27.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4719
_reflns_number_gt                4124
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0332P)²+0.5228P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1566 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4719
_refine_ls_number_parameters     247
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0773
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.31793(4) 0.80904(8) 0.49887(2) 0.02578(13) Uani 1 1 d . . . . .
O1 O 0.7484(3) 0.8830(4) 0.28964(14) 0.0164(6) Uani 1 1 d . . . . .
N1 N 0.6666(4) 0.6847(6) 0.28475(18) 0.0145(7) Uani 1 1 d . . . . .
C1 C 0.5481(4) 0.6398(7) 0.3270(2) 0.0143(8) Uani 1 1 d . . . . .
C2 C 0.5050(4) 0.7536(6) 0.38562(19) 0.0144(9) Uani 1 1 d . . . . .
H2 H 0.556018 0.882366 0.401961 0.017 Uiso 1 1 calc R U . . .
C3 C 0.3820(5) 0.6632(8) 0.4179(2) 0.0175(9) Uani 1 1 d . . . . .
C4 C 0.3039(5) 0.4702(7) 0.3947(2) 0.0189(9) Uani 1 1 d . . . . .
H4 H 0.225336 0.410942 0.419774 0.023 Uiso 1 1 calc R U . . .
C5 C 0.3438(4) 0.3673(7) 0.3341(2) 0.0180(10) Uani 1 1 d . . . . .
H5 H 0.288924 0.242242 0.317134 0.022 Uiso 1 1 calc R U . . .
C6 C 0.4675(5) 0.4522(7) 0.2983(2) 0.0152(8) Uani 1 1 d . . . . .
C7 C 0.5337(4) 0.3972(7) 0.2336(2) 0.0144(8) Uani 1 1 d . . . . .
C8 C 0.4725(4) 0.2344(7) 0.1809(2) 0.0148(9) Uani 1 1 d . . . . .
C9 C 0.4689(4) 0.2831(9) 0.10909(18) 0.0188(9) Uani 1 1 d . . . . .
H9 H 0.507829 0.418698 0.094918 0.023 Uiso 1 1 calc R U . . .
C10 C 0.4087(5) 0.1334(8) 0.0590(2) 0.0243(10) Uani 1 1 d . . . . .
H10 H 0.408730 0.168594 0.011722 0.029 Uiso 1 1 calc R U . . .
C11 C 0.3483(5) -0.0684(8) 0.0787(2) 0.0257(11) Uani 1 1 d . . . . .
H11 H 0.307543 -0.168537 0.044895 0.031 Uiso 1 1 calc R U . . .
C12 C 0.3490(5) -0.1202(7) 0.1497(2) 0.0232(10) Uani 1 1 d . . . . .
H12 H 0.307616 -0.254648 0.163480 0.028 Uiso 1 1 calc R U . . .
C13 C 0.4114(5) 0.0291(7) 0.1997(2) 0.0170(9) Uani 1 1 d . . . . .
H13 H 0.412833 -0.008073 0.246888 0.020 Uiso 1 1 calc R U . . .
C14 C 0.6538(5) 0.5462(7) 0.2264(2) 0.0149(8) Uani 1 1 d . . . . .
C15 C 0.7657(5) 0.5635(8) 0.1717(2) 0.0188(9) Uani 1 1 d . . . . .
C16 C 0.7777(5) 0.7631(9) 0.1349(2) 0.0271(12) Uani 1 1 d . . . . .
H16 H 0.713134 0.883030 0.143156 0.033 Uiso 1 1 calc R U . . .
C17 C 0.8876(6) 0.7786(12) 0.0860(2) 0.0409(16) Uani 1 1 d . . . . .
H17 H 0.896024 0.909773 0.060909 0.049 Uiso 1 1 calc R U . . .
C18 C 0.9844(7) 0.6026(12) 0.0741(3) 0.0506(19) Uani 1 1 d . . . . .
H18 H 1.059253 0.617152 0.041919 0.061 Uiso 1 1 calc R U . . .
C19 C 0.9714(6) 0.4045(10) 0.1096(3) 0.0444(16) Uani 1 1 d . . . . .
H19 H 1.036700 0.285717 0.101020 0.053 Uiso 1 1 calc R U . . .
C20 C 0.8602(5) 0.3831(8) 0.1583(2) 0.0271(11) Uani 1 1 d . . . . .
H20 H 0.849344 0.249083 0.181592 0.033 Uiso 1 1 calc R U . . .
C21 C 0.9038(4) 0.8738(7) 0.3316(2) 0.0182(10) Uani 1 1 d . . . . .
C22 C 0.8967(5) 0.7359(8) 0.3975(2) 0.0257(11) Uani 1 1 d . . . . .
H22A H 0.820168 0.798167 0.425714 0.039 Uiso 1 1 calc R U . . .
H22B H 0.997641 0.736040 0.423499 0.039 Uiso 1 1 calc R U . . .
H22C H 0.867615 0.586007 0.384884 0.039 Uiso 1 1 calc R U . . .
C23 C 0.9294(6) 1.1166(8) 0.3495(3) 0.0290(11) Uani 1 1 d . . . . .
H23A H 0.932179 1.201228 0.307121 0.044 Uiso 1 1 calc R U . . .
H23B H 1.027176 1.133768 0.377580 0.044 Uiso 1 1 calc R U . . .
H23C H 0.845253 1.169099 0.375261 0.044 Uiso 1 1 calc R U . . .
C24 C 1.0270(4) 0.7899(12) 0.2859(2) 0.0259(10) Uani 1 1 d . . . . .
H24A H 1.009407 0.634964 0.275986 0.039 Uiso 1 1 calc R U . . .
H24B H 1.129197 0.809155 0.309997 0.039 Uiso 1 1 calc R U . . .
H24C H 1.020572 0.872179 0.242814 0.039 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
Br1 C3 1.902(4) . ?
O1 N1 1.382(4) . ?
O1 C21 1.494(5) . ?
N1 C1 1.376(5) . ?
N1 C14 1.390(5) . ?
C1 C2 1.391(5) . ?
C1 C6 1.409(6) . ?
C2 C3 1.377(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(6) . ?
C4 C5 1.383(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.406(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.443(6) . ?
C7 C14 1.379(6) . ?
C7 C8 1.470(5) . ?
C8 C13 1.399(6) . ?
C8 C9 1.403(5) . ?
C9 C10 1.382(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.393(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(6) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.482(6) . ?
C15 C20 1.390(6) . ?
C15 C16 1.400(7) . ?
C16 C17 1.385(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.380(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.393(7) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C23 1.512(6) . ?
C21 C24 1.512(6) . ?
C21 C22 1.515(6) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
N1 O1 C21 115.2(3) . . ?
C1 N1 O1 121.6(3) . . ?
C1 N1 C14 110.1(3) . . ?
O1 N1 C14 125.2(3) . . ?
N1 C1 C2 129.6(4) . . ?
N1 C1 C6 106.7(3) . . ?
C2 C1 C6 123.7(4) . . ?
C3 C2 C1 115.7(4) . . ?
C3 C2 H2 122.1 . . ?
C1 C2 H2 122.1 . . ?
C2 C3 C4 123.3(4) . . ?
C2 C3 Br1 118.0(3) . . ?
C4 C3 Br1 118.7(3) . . ?
C5 C4 C3 119.7(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 119.8(4) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 117.7(4) . . ?
C5 C6 C7 134.6(4) . . ?
C1 C6 C7 107.7(3) . . ?
C14 C7 C6 106.7(3) . . ?
C14 C7 C8 126.1(4) . . ?
C6 C7 C8 126.8(4) . . ?
C13 C8 C9 117.3(4) . . ?
C13 C8 C7 122.0(4) . . ?
C9 C8 C7 120.7(4) . . ?
C10 C9 C8 121.3(4) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 120.5(4) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C12 119.4(4) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 119.9(4) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C8 121.6(4) . . ?
C12 C13 H13 119.2 . . ?
C8 C13 H13 119.2 . . ?
C7 C14 N1 108.5(3) . . ?
C7 C14 C15 130.4(4) . . ?
N1 C14 C15 121.0(4) . . ?
C20 C15 C16 120.5(4) . . ?
C20 C15 C14 119.8(4) . . ?
C16 C15 C14 119.7(4) . . ?
C17 C16 C15 118.7(5) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C18 C17 C16 120.9(5) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 120.5(5) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C20 119.8(5) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C15 C20 C19 119.5(5) . . ?
C15 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
O1 C21 C23 101.0(3) . . ?
O1 C21 C24 109.5(3) . . ?
C23 C21 C24 111.0(4) . . ?
O1 C21 C22 111.7(3) . . ?
C23 C21 C22 110.8(4) . . ?
C24 C21 C22 112.2(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C21 O1 N1 C1 98.9(4) . . . . ?
C21 O1 N1 C14 -103.2(4) . . . . ?
O1 N1 C1 C2 -10.9(6) . . . . ?
C14 N1 C1 C2 -171.7(4) . . . . ?
O1 N1 C1 C6 166.9(3) . . . . ?
C14 N1 C1 C6 6.1(4) . . . . ?
N1 C1 C2 C3 -178.6(4) . . . . ?
C6 C1 C2 C3 4.0(6) . . . . ?
C1 C2 C3 C4 0.2(6) . . . . ?
C1 C2 C3 Br1 179.5(3) . . . . ?
C2 C3 C4 C5 -3.6(7) . . . . ?
Br1 C3 C4 C5 177.0(3) . . . . ?
C3 C4 C5 C6 2.9(6) . . . . ?
C4 C5 C6 C1 1.0(6) . . . . ?
C4 C5 C6 C7 -176.0(4) . . . . ?
N1 C1 C6 C5 177.4(4) . . . . ?
C2 C1 C6 C5 -4.6(6) . . . . ?
N1 C1 C6 C7 -4.8(4) . . . . ?
C2 C1 C6 C7 173.1(4) . . . . ?
C5 C6 C7 C14 179.1(4) . . . . ?
C1 C6 C7 C14 1.9(4) . . . . ?
C5 C6 C7 C8 6.5(7) . . . . ?
C1 C6 C7 C8 -170.7(4) . . . . ?
C14 C7 C8 C13 148.5(4) . . . . ?
C6 C7 C8 C13 -40.3(6) . . . . ?
C14 C7 C8 C9 -33.5(6) . . . . ?
C6 C7 C8 C9 137.7(4) . . . . ?
C13 C8 C9 C10 -0.5(6) . . . . ?
C7 C8 C9 C10 -178.6(4) . . . . ?
C8 C9 C10 C11 0.8(7) . . . . ?
C9 C10 C11 C12 -0.2(7) . . . . ?
C10 C11 C12 C13 -0.7(7) . . . . ?
C11 C12 C13 C8 1.0(6) . . . . ?
C9 C8 C13 C12 -0.4(6) . . . . ?
C7 C8 C13 C12 177.7(4) . . . . ?
C6 C7 C14 N1 1.8(4) . . . . ?
C8 C7 C14 N1 174.4(4) . . . . ?
C6 C7 C14 C15 177.6(4) . . . . ?
C8 C7 C14 C15 -9.8(7) . . . . ?
C1 N1 C14 C7 -4.9(5) . . . . ?
O1 N1 C14 C7 -164.9(3) . . . . ?
C1 N1 C14 C15 178.8(4) . . . . ?
O1 N1 C14 C15 18.8(6) . . . . ?
C7 C14 C15 C20 -57.0(6) . . . . ?
N1 C14 C15 C20 118.4(5) . . . . ?
C7 C14 C15 C16 124.4(5) . . . . ?
N1 C14 C15 C16 -60.3(5) . . . . ?
C20 C15 C16 C17 -1.3(6) . . . . ?
C14 C15 C16 C17 177.4(4) . . . . ?
C15 C16 C17 C18 -0.6(6) . . . . ?
C16 C17 C18 C19 1.6(7) . . . . ?
C17 C18 C19 C20 -0.5(8) . . . . ?
C16 C15 C20 C19 2.3(6) . . . . ?
C14 C15 C20 C19 -176.3(4) . . . . ?
C18 C19 C20 C15 -1.4(7) . . . . ?
N1 O1 C21 C23 -159.2(3) . . . . ?
N1 O1 C21 C24 83.6(4) . . . . ?
N1 O1 C21 C22 -41.4(4) . . . . ?

_refine_diff_density_max         0.991
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.070



