# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

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

data_2a
_database_code_depnum_ccdc_archive 'CCDC 2244539'
loop_
_audit_author_name
_audit_author_address
'Tatsuhiro KOJIMA'
;Osaka University
Japan
;
_audit_update_record             
;
2023-02-25 deposited with the CCDC.	2023-07-24 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            'C22 H27 N O2'
_chemical_formula_weight         337.44

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.9726(15)
_cell_length_b                   10.7845(4)
_cell_length_c                   18.1114(11)
_cell_angle_alpha                90
_cell_angle_beta                 124.638(9)
_cell_angle_gamma                90
_cell_volume                     3852.5(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    5311
_cell_measurement_theta_min      2.0760
_cell_measurement_theta_max      31.2970

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_F_000             1456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_T_min  0.858
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.60a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            16592
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.065
_diffrn_reflns_theta_max         30.759
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.823
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.823
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4945
_reflns_number_gt                3572
_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       'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.75a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    Mercury
_computing_publication_material  WinGX
_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)+(0.0431P)²+1.7563P] 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         4945
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
C1 C 0.62928(6) 0.10658(12) 0.50302(8) 0.0233(3) Uani 1 1 d . . . . .
C2 C 0.62413(6) 0.20585(12) 0.54268(8) 0.0230(3) Uani 1 1 d . . . . .
H2 H 0.591812 0.201698 0.557184 0.028 Uiso 1 1 calc R U . . .
C3 C 0.66450(6) 0.32393(11) 0.56673(8) 0.0207(3) Uani 1 1 d . . . . .
H3 H 0.706783 0.305508 0.570122 0.025 Uiso 1 1 calc R U . . .
C4 C 0.62583(6) 0.42440(11) 0.49705(8) 0.0212(3) Uani 1 1 d . . . . .
C5 C 0.52599(7) 0.54458(14) 0.42069(9) 0.0333(3) Uani 1 1 d . . . . .
H5A H 0.487030 0.563736 0.422951 0.050 Uiso 1 1 calc R U . . .
H5B H 0.509927 0.513085 0.360955 0.050 Uiso 1 1 calc R U . . .
H5C H 0.552793 0.619944 0.432950 0.050 Uiso 1 1 calc R U . . .
C6 C 0.67482(8) 0.09602(15) 0.47186(11) 0.0390(4) Uani 1 1 d . . . . .
H6A H 0.699257 0.174262 0.483246 0.058 Uiso 1 1 calc R U . . .
H6B H 0.647697 0.078061 0.407396 0.058 Uiso 1 1 calc R U . . .
H6C H 0.707425 0.028807 0.504453 0.058 Uiso 1 1 calc R U . . .
C7 C 0.58694(8) -0.00710(13) 0.48564(11) 0.0375(4) Uani 1 1 d . . . . .
H7A H 0.557612 0.007589 0.506362 0.056 Uiso 1 1 calc R U . . .
H7B H 0.616742 -0.077836 0.518082 0.056 Uiso 1 1 calc R U . . .
H7C H 0.558933 -0.024999 0.421165 0.056 Uiso 1 1 calc R U . . .
C8 C 0.68503(6) 0.37180(11) 0.65884(8) 0.0203(3) Uani 1 1 d . . . . .
H8A H 0.643742 0.386571 0.657576 0.024 Uiso 1 1 calc R U . . .
H8B H 0.712453 0.307837 0.704872 0.024 Uiso 1 1 calc R U . . .
C9 C 0.72643(6) 0.54816(12) 0.75739(8) 0.0211(3) Uani 1 1 d . . . . .
H9A H 0.764924 0.607060 0.786965 0.025 Uiso 1 1 calc R U . . .
H9B H 0.734924 0.484946 0.802318 0.025 Uiso 1 1 calc R U . . .
C10 C 0.66233(6) 0.61735(11) 0.72802(8) 0.0203(3) Uani 1 1 d . . . . .
C11 C 0.64208(7) 0.62853(12) 0.78607(9) 0.0256(3) Uani 1 1 d . . . . .
H11 H 0.667529 0.588545 0.842854 0.031 Uiso 1 1 calc R U . . .
C12 C 0.58526(7) 0.69724(14) 0.76215(10) 0.0311(3) Uani 1 1 d . . . . .
H12 H 0.572357 0.704844 0.802769 0.037 Uiso 1 1 calc R U . . .
C13 C 0.54722(7) 0.75490(12) 0.67907(10) 0.0297(3) Uani 1 1 d . . . . .
H13 H 0.508213 0.801890 0.662532 0.036 Uiso 1 1 calc R U . . .
C14 C 0.56647(6) 0.74351(12) 0.62052(9) 0.0266(3) Uani 1 1 d . . . . .
H14 H 0.540310 0.782245 0.563322 0.032 Uiso 1 1 calc R U . . .
C15 C 0.62367(6) 0.67599(11) 0.64464(8) 0.0228(3) Uani 1 1 d . . . . .
H15 H 0.636688 0.669546 0.604076 0.027 Uiso 1 1 calc R U . . .
C16 C 0.79367(6) 0.46426(11) 0.70966(9) 0.0226(3) Uani 1 1 d . . . . .
H16A H 0.792564 0.401680 0.668850 0.027 Uiso 1 1 calc R U . . .
H16B H 0.820953 0.429896 0.771252 0.027 Uiso 1 1 calc R U . . .
C17 C 0.82746(6) 0.58070(11) 0.70667(8) 0.0209(3) Uani 1 1 d . . . . .
C18 C 0.89594(7) 0.60081(13) 0.77095(9) 0.0264(3) Uani 1 1 d . . . . .
H18 H 0.920886 0.543202 0.818645 0.032 Uiso 1 1 calc R U . . .
C19 C 0.92846(7) 0.70416(14) 0.76643(10) 0.0330(3) Uani 1 1 d . . . . .
H19 H 0.975472 0.716345 0.810608 0.040 Uiso 1 1 calc R U . . .
C20 C 0.89263(7) 0.78943(13) 0.69780(10) 0.0325(3) Uani 1 1 d . . . . .
H20 H 0.914739 0.860537 0.694977 0.039 Uiso 1 1 calc R U . . .
C21 C 0.82427(7) 0.77019(13) 0.63329(10) 0.0299(3) Uani 1 1 d . . . . .
H21 H 0.799453 0.828193 0.585847 0.036 Uiso 1 1 calc R U . . .
C22 C 0.79182(7) 0.66676(12) 0.63752(9) 0.0252(3) Uani 1 1 d . . . . .
H22 H 0.744897 0.654447 0.592908 0.030 Uiso 1 1 calc R U . . .
N1 N 0.72416(5) 0.48677(9) 0.68346(7) 0.0182(2) Uani 1 1 d . . . . .
O1 O 0.56758(4) 0.45175(8) 0.48727(6) 0.0269(2) Uani 1 1 d . . . . .
O2 O 0.64419(5) 0.47393(10) 0.45490(6) 0.0345(2) Uani 1 1 d . . . . .


_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
C1 C2 1.3335(18) . ?
C1 C6 1.4912(19) . ?
C1 C7 1.5062(19) . ?
C2 C3 1.5062(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.5153(18) . ?
C3 C8 1.5356(16) . ?
C3 H3 1.0000 . ?
C4 O2 1.2014(15) . ?
C4 O1 1.3368(15) . ?
C5 O1 1.4436(16) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N1 1.4630(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N1 1.4667(15) . ?
C9 C10 1.5073(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.3913(18) . ?
C10 C15 1.3958(17) . ?
C11 C12 1.3860(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3859(18) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 N1 1.4704(16) . ?
C16 C17 1.5119(17) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.3873(18) . ?
C17 C22 1.3942(18) . ?
C18 C19 1.3891(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.384(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.3867(19) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

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
C2 C1 C6 125.24(12) . . ?
C2 C1 C7 120.55(12) . . ?
C6 C1 C7 114.21(12) . . ?
C1 C2 C3 126.41(12) . . ?
C1 C2 H2 116.8 . . ?
C3 C2 H2 116.8 . . ?
C2 C3 C4 112.04(10) . . ?
C2 C3 C8 110.79(10) . . ?
C4 C3 C8 109.33(10) . . ?
C2 C3 H3 108.2 . . ?
C4 C3 H3 108.2 . . ?
C8 C3 H3 108.2 . . ?
O2 C4 O1 123.36(12) . . ?
O2 C4 C3 125.13(12) . . ?
O1 C4 C3 111.50(10) . . ?
O1 C5 H5A 109.5 . . ?
O1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C3 111.73(10) . . ?
N1 C8 H8A 109.3 . . ?
C3 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C3 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
N1 C9 C10 113.58(10) . . ?
N1 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C15 118.43(12) . . ?
C11 C10 C9 119.99(11) . . ?
C15 C10 C9 121.52(11) . . ?
C12 C11 C10 120.87(12) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 120.16(13) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 119.50(13) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 120.47(12) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 120.57(12) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
N1 C16 C17 112.54(10) . . ?
N1 C16 H16A 109.1 . . ?
C17 C16 H16A 109.1 . . ?
N1 C16 H16B 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C22 118.59(12) . . ?
C18 C17 C16 120.15(12) . . ?
C22 C17 C16 121.19(11) . . ?
C17 C18 C19 120.80(13) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C20 C19 C18 120.24(13) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.41(13) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C20 C21 C22 120.40(13) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C17 120.56(12) . . ?
C21 C22 H22 119.7 . . ?
C17 C22 H22 119.7 . . ?
C8 N1 C9 110.22(9) . . ?
C8 N1 C16 111.78(9) . . ?
C9 N1 C16 109.44(9) . . ?
C4 O1 C5 115.92(10) . . ?

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
C6 C1 C2 C3 -2.4(2) . . . . ?
C7 C1 C2 C3 178.03(12) . . . . ?
C1 C2 C3 C4 97.93(15) . . . . ?
C1 C2 C3 C8 -139.68(13) . . . . ?
C2 C3 C4 O2 -120.38(14) . . . . ?
C8 C3 C4 O2 116.40(13) . . . . ?
C2 C3 C4 O1 59.29(13) . . . . ?
C8 C3 C4 O1 -63.93(13) . . . . ?
C2 C3 C8 N1 -179.82(10) . . . . ?
C4 C3 C8 N1 -55.86(13) . . . . ?
N1 C9 C10 C11 149.10(11) . . . . ?
N1 C9 C10 C15 -33.75(16) . . . . ?
C15 C10 C11 C12 -0.63(19) . . . . ?
C9 C10 C11 C12 176.60(12) . . . . ?
C10 C11 C12 C13 0.7(2) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
C12 C13 C14 C15 -0.6(2) . . . . ?
C13 C14 C15 C10 0.68(19) . . . . ?
C11 C10 C15 C14 -0.07(18) . . . . ?
C9 C10 C15 C14 -177.26(11) . . . . ?
N1 C16 C17 C18 142.76(12) . . . . ?
N1 C16 C17 C22 -40.39(16) . . . . ?
C22 C17 C18 C19 -0.27(19) . . . . ?
C16 C17 C18 C19 176.66(12) . . . . ?
C17 C18 C19 C20 0.6(2) . . . . ?
C18 C19 C20 C21 -0.6(2) . . . . ?
C19 C20 C21 C22 0.3(2) . . . . ?
C20 C21 C22 C17 0.0(2) . . . . ?
C18 C17 C22 C21 -0.02(19) . . . . ?
C16 C17 C22 C21 -176.91(12) . . . . ?
C3 C8 N1 C9 164.05(10) . . . . ?
C3 C8 N1 C16 -74.01(12) . . . . ?
C10 C9 N1 C8 -78.29(12) . . . . ?
C10 C9 N1 C16 158.40(10) . . . . ?
C17 C16 N1 C8 161.73(10) . . . . ?
C17 C16 N1 C9 -75.88(12) . . . . ?
O2 C4 O1 C5 1.12(18) . . . . ?
C3 C4 O1 C5 -178.56(10) . . . . ?

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.040



