# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_samp2
_database_code_depnum_ccdc_archive 'CCDC 2237321'
loop_
_audit_author_name
_audit_author_address
'Hiroyuki Yamakoshi'
;Nagoya City University
Japan
;
_audit_update_record             
;
2023-01-20 deposited with the CCDC.	2024-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H29 N O5'
_chemical_formula_sum            'C21 H29 N O5'
_chemical_formula_weight         375.45

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                   7.6082(4)
_cell_length_b                   11.0116(11)
_cell_length_c                   10.8744(13)
_cell_angle_alpha                89.490(9)
_cell_angle_beta                 98.254(7)
_cell_angle_gamma                89.986(6)
_cell_volume                     901.57(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    6935
_cell_measurement_theta_min      2.6220
_cell_measurement_theta_max      30.8580

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'Rigaku VariMax Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            14919
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_av_R_equivalents  0.1089
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.849
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3335
_reflns_number_gt                2740
_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       CrystalClear
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2011 (Wakita Nemoto et al., 2011)'
_computing_publication_material  
;Yadokari-XG 2011 (Wakita,Nemoto et al., 2011)
;
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] 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         3335
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1234
_refine_ls_R_factor_gt           0.1083
_refine_ls_wR_factor_ref         0.3177
_refine_ls_wR_factor_gt          0.2898
_refine_ls_goodness_of_fit_ref   1.322
_refine_ls_restrained_S_all      1.322
_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 0.4246(4) 0.9480(4) 0.2659(4) 0.0381(10) Uani 1 1 d . . . . .
O2 O 0.9271(4) 0.5513(4) 0.7690(3) 0.0356(9) Uani 1 1 d . . . . .
C1 C 0.8396(6) 0.6462(5) 0.5302(5) 0.0338(12) Uani 1 1 d . . . . .
H1 H 0.9041 0.5682 0.5529 0.041 Uiso 1 1 calc R U . . .
O3 O 0.6230(5) 1.1212(4) 0.1838(4) 0.0420(10) Uani 1 1 d . . . . .
O4 O 0.8073(5) 0.7130(4) 0.8472(4) 0.0419(10) Uani 1 1 d . . . . .
C2 C 0.4398(6) 0.6437(6) 0.2020(5) 0.0363(13) Uani 1 1 d . . . . .
H2 H 0.5127 0.7038 0.1619 0.044 Uiso 1 1 calc R U . . .
O5 O 0.2806(5) 0.6213(4) 0.1176(4) 0.0401(10) Uani 1 1 d . . . . .
H3 H 0.2219 0.6860 0.1052 0.060 Uiso 1 1 calc R U . . .
C4 C 0.6728(6) 0.6194(5) 0.4388(5) 0.0338(12) Uani 1 1 d . . . . .
H4 H 0.5978 0.5624 0.4809 0.041 Uiso 1 1 calc R U . . .
N1 N 0.7873(5) 0.6988(5) 0.6422(4) 0.0366(11) Uani 1 1 d . . . . .
C6 C 0.3959(6) 0.6984(5) 0.3202(5) 0.0351(13) Uani 1 1 d . . . . .
H5 H 0.3290 0.6385 0.3636 0.042 Uiso 1 1 calc R U . . .
H6 H 0.3190 0.7703 0.2997 0.042 Uiso 1 1 calc R U . . .
C7 C 0.5137(6) 0.7826(5) 0.5279(5) 0.0345(13) Uani 1 1 d . . . . .
H7 H 0.4357 0.7221 0.5609 0.041 Uiso 1 1 calc R U . . .
H8 H 0.4453 0.8589 0.5112 0.041 Uiso 1 1 calc R U . . .
C8 C 0.8960(7) 1.0218(5) 0.2791(5) 0.0359(13) Uani 1 1 d . . . . .
H20 H 0.9693 1.0833 0.2516 0.043 Uiso 1 1 calc R U . . .
C9 C 0.5492(7) 0.5313(6) 0.2310(5) 0.0377(13) Uani 1 1 d . . . . .
H9 H 0.5840 0.4989 0.1534 0.045 Uiso 1 1 calc R U . . .
H10 H 0.4772 0.4687 0.2666 0.045 Uiso 1 1 calc R U . . .
C10 C 0.6746(6) 0.8059(6) 0.6257(6) 0.0380(13) Uani 1 1 d . . . . .
H11 H 0.7430 0.8756 0.5994 0.046 Uiso 1 1 calc R U . . .
H12 H 0.6344 0.8267 0.7056 0.046 Uiso 1 1 calc R U . . .
C11 C 0.8654(8) 0.7703(7) 1.0562(6) 0.0467(15) Uani 1 1 d . . . . .
H13 H 0.9065 0.7432 1.1416 0.070 Uiso 1 1 calc R U . . .
H14 H 0.9436 0.8347 1.0332 0.070 Uiso 1 1 calc R U . . .
H15 H 0.7438 0.8014 1.0504 0.070 Uiso 1 1 calc R U . . .
C12 C 0.9621(6) 0.7319(6) 0.4689(5) 0.0359(13) Uani 1 1 d . . . . .
H21 H 1.0476 0.7694 0.5349 0.043 Uiso 1 1 calc R U . . .
H22 H 1.0310 0.6832 0.4164 0.043 Uiso 1 1 calc R U . . .
C13 C 0.7167(6) 0.5573(6) 0.3235(5) 0.0361(13) Uani 1 1 d . . . . .
H16 H 0.7792 0.4800 0.3476 0.043 Uiso 1 1 calc R U . . .
H17 H 0.7976 0.6096 0.2829 0.043 Uiso 1 1 calc R U . . .
C14 C 0.6083(6) 0.9337(6) 0.2878(5) 0.0346(13) Uani 1 1 d . . . . .
C15 C 0.8670(6) 0.8313(5) 0.3902(5) 0.0332(12) Uani 1 1 d . . . . .
C16 C 0.7122(6) 1.0275(5) 0.2486(5) 0.0356(13) Uani 1 1 d . . . . .
C17 C 0.6800(6) 0.8350(5) 0.3560(5) 0.0318(12) Uani 1 1 d . . . . .
C18 C 0.9694(6) 0.9256(6) 0.3497(5) 0.0391(14) Uani 1 1 d . . . . .
H23 H 1.0947 0.9227 0.3721 0.047 Uiso 1 1 calc R U . . .
C19 C 0.8475(6) 0.6462(6) 0.7522(5) 0.0362(13) Uani 1 1 d . . . . .
C20 C 0.5652(6) 0.7366(5) 0.4078(5) 0.0349(13) Uani 1 1 d . . . . .
C21 C 0.7239(8) 1.2236(6) 0.1520(6) 0.0443(14) Uani 1 1 d . . . . .
H24 H 0.6440 1.2835 0.1061 0.066 Uiso 1 1 calc R U . . .
H25 H 0.7852 1.2603 0.2280 0.066 Uiso 1 1 calc R U . . .
H26 H 0.8115 1.1969 0.1000 0.066 Uiso 1 1 calc R U . . .
C22 C 0.3418(7) 0.9521(6) 0.1400(6) 0.0422(14) Uani 1 1 d . . . . .
H27 H 0.2134 0.9623 0.1373 0.063 Uiso 1 1 calc R U . . .
H28 H 0.3895 1.0206 0.0971 0.063 Uiso 1 1 calc R U . . .
H29 H 0.3657 0.8762 0.0989 0.063 Uiso 1 1 calc R U . . .
C23 C 0.8691(7) 0.6660(6) 0.9702(5) 0.0402(14) Uani 1 1 d . . . . .
H18 H 0.9912 0.6335 0.9747 0.048 Uiso 1 1 calc R U . . .
H19 H 0.7904 0.6001 0.9920 0.048 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 C14 1.392(5) . ?
O1 C22 1.423(7) . ?
O2 C19 1.207(8) . ?
C1 N1 1.459(7) . ?
C1 C4 1.526(6) . ?
C1 C12 1.540(7) . ?
O3 C16 1.367(7) . ?
O3 C21 1.432(7) . ?
O4 C19 1.344(7) . ?
O4 C23 1.444(7) . ?
C2 O5 1.434(6) . ?
C2 C9 1.497(8) . ?
C2 C6 1.505(8) . ?
C4 C13 1.512(8) . ?
C4 C20 1.536(8) . ?
N1 C19 1.344(7) . ?
N1 C10 1.453(8) . ?
C6 C20 1.548(7) . ?
C7 C20 1.508(8) . ?
C7 C10 1.525(7) . ?
C8 C18 1.374(8) . ?
C8 C16 1.392(7) . ?
C9 C13 1.534(7) . ?
C11 C23 1.490(10) . ?
C12 C15 1.503(8) . ?
C14 C17 1.378(8) . ?
C14 C16 1.401(8) . ?
C15 C18 1.403(8) . ?
C15 C17 1.418(6) . ?
C17 C20 1.544(7) . ?

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
C14 O1 C22 117.5(4) . . ?
N1 C1 C4 108.9(4) . . ?
N1 C1 C12 111.7(5) . . ?
C4 C1 C12 109.7(4) . . ?
C16 O3 C21 118.0(4) . . ?
C19 O4 C23 116.0(5) . . ?
O5 C2 C9 112.4(5) . . ?
O5 C2 C6 110.4(4) . . ?
C9 C2 C6 109.9(4) . . ?
C13 C4 C1 111.7(4) . . ?
C13 C4 C20 112.2(4) . . ?
C1 C4 C20 110.1(5) . . ?
C19 N1 C10 124.9(5) . . ?
C19 N1 C1 118.2(5) . . ?
C10 N1 C1 116.9(4) . . ?
C2 C6 C20 111.8(4) . . ?
C20 C7 C10 112.4(4) . . ?
C18 C8 C16 118.7(5) . . ?
C2 C9 C13 111.3(5) . . ?
N1 C10 C7 110.1(5) . . ?
C15 C12 C1 114.5(4) . . ?
C4 C13 C9 111.8(4) . . ?
C17 C14 O1 119.3(4) . . ?
C17 C14 C16 122.9(4) . . ?
O1 C14 C16 117.6(5) . . ?
C18 C15 C17 118.7(5) . . ?
C18 C15 C12 117.9(4) . . ?
C17 C15 C12 123.4(5) . . ?
O3 C16 C8 124.2(5) . . ?
O3 C16 C14 116.6(4) . . ?
C8 C16 C14 119.2(5) . . ?
C14 C17 C15 117.8(5) . . ?
C14 C17 C20 122.9(4) . . ?
C15 C17 C20 119.0(5) . . ?
C8 C18 C15 122.8(4) . . ?
O2 C19 N1 126.9(6) . . ?
O2 C19 O4 121.8(5) . . ?
N1 C19 O4 111.3(5) . . ?
C7 C20 C4 107.1(4) . . ?
C7 C20 C17 107.9(5) . . ?
C4 C20 C17 110.7(4) . . ?
C7 C20 C6 109.3(4) . . ?
C4 C20 C6 105.8(5) . . ?
C17 C20 C6 115.7(4) . . ?
O4 C23 C11 106.1(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
N1 C1 C4 C13 -176.4(4) . . . . ?
C12 C1 C4 C13 61.1(6) . . . . ?
N1 C1 C4 C20 58.3(5) . . . . ?
C12 C1 C4 C20 -64.2(6) . . . . ?
C4 C1 N1 C19 125.8(5) . . . . ?
C12 C1 N1 C19 -112.9(5) . . . . ?
C4 C1 N1 C10 -54.8(6) . . . . ?
C12 C1 N1 C10 66.5(5) . . . . ?
O5 C2 C6 C20 -173.9(4) . . . . ?
C9 C2 C6 C20 61.6(5) . . . . ?
O5 C2 C9 C13 -178.8(4) . . . . ?
C6 C2 C9 C13 -55.4(6) . . . . ?
C19 N1 C10 C7 -129.1(5) . . . . ?
C1 N1 C10 C7 51.5(6) . . . . ?
C20 C7 C10 N1 -52.7(6) . . . . ?
N1 C1 C12 C15 -80.6(5) . . . . ?
C4 C1 C12 C15 40.2(7) . . . . ?
C1 C4 C13 C9 -179.5(5) . . . . ?
C20 C4 C13 C9 -55.4(6) . . . . ?
C2 C9 C13 C4 53.0(6) . . . . ?
C22 O1 C14 C17 -120.9(6) . . . . ?
C22 O1 C14 C16 65.0(7) . . . . ?
C1 C12 C15 C18 168.7(5) . . . . ?
C1 C12 C15 C17 -10.8(8) . . . . ?
C21 O3 C16 C8 -4.0(9) . . . . ?
C21 O3 C16 C14 174.6(5) . . . . ?
C18 C8 C16 O3 176.9(5) . . . . ?
C18 C8 C16 C14 -1.7(9) . . . . ?
C17 C14 C16 O3 -178.6(5) . . . . ?
O1 C14 C16 O3 -4.7(8) . . . . ?
C17 C14 C16 C8 0.1(9) . . . . ?
O1 C14 C16 C8 174.0(5) . . . . ?
O1 C14 C17 C15 -172.0(5) . . . . ?
C16 C14 C17 C15 1.8(9) . . . . ?
O1 C14 C17 C20 1.4(9) . . . . ?
C16 C14 C17 C20 175.2(6) . . . . ?
C18 C15 C17 C14 -2.0(9) . . . . ?
C12 C15 C17 C14 177.4(5) . . . . ?
C18 C15 C17 C20 -175.7(5) . . . . ?
C12 C15 C17 C20 3.7(9) . . . . ?
C16 C8 C18 C15 1.4(9) . . . . ?
C17 C15 C18 C8 0.5(9) . . . . ?
C12 C15 C18 C8 -179.0(6) . . . . ?
C10 N1 C19 O2 172.5(5) . . . . ?
C1 N1 C19 O2 -8.2(7) . . . . ?
C10 N1 C19 O4 -7.1(7) . . . . ?
C1 N1 C19 O4 172.2(4) . . . . ?
C23 O4 C19 O2 1.6(7) . . . . ?
C23 O4 C19 N1 -178.8(4) . . . . ?
C10 C7 C20 C4 58.1(5) . . . . ?
C10 C7 C20 C17 -61.1(6) . . . . ?
C10 C7 C20 C6 172.3(5) . . . . ?
C13 C4 C20 C7 174.2(4) . . . . ?
C1 C4 C20 C7 -60.8(5) . . . . ?
C13 C4 C20 C17 -68.5(5) . . . . ?
C1 C4 C20 C17 56.6(6) . . . . ?
C13 C4 C20 C6 57.6(5) . . . . ?
C1 C4 C20 C6 -177.4(4) . . . . ?
C14 C17 C20 C7 -82.7(6) . . . . ?
C15 C17 C20 C7 90.6(6) . . . . ?
C14 C17 C20 C4 160.4(5) . . . . ?
C15 C17 C20 C4 -26.3(7) . . . . ?
C14 C17 C20 C6 40.1(8) . . . . ?
C15 C17 C20 C6 -146.6(6) . . . . ?
C2 C6 C20 C7 -176.1(4) . . . . ?
C2 C6 C20 C4 -61.1(5) . . . . ?
C2 C6 C20 C17 61.9(6) . . . . ?
C19 O4 C23 C11 161.3(4) . . . . ?

_refine_diff_density_max         0.525
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.097



