# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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. 
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data_mo_2023158_0m
_database_code_depnum_ccdc_archive 'CCDC 2258994'
loop_
_audit_author_name
_audit_author_address
'Zaiyong Zhang'
;Shanghai Institute of Materia Medica, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-04-26 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_audit_creation_date             2023-02-14
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.01.27 svn.rdd5efbe3 for OlexSys, GUI svn.r6708)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N O3'
_chemical_formula_sum            'C20 H21 N O3'
_chemical_formula_weight         323.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.1141(4)
_cell_length_b                   14.4848(6)
_cell_length_c                   20.8204(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3351.8(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6430
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.281
_cell_measurement_theta_min      2.681
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0872 before and 0.0492 after correction.
The Ratio of minimum to maximum transmission is 0.8764.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24220
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_min         2.681
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2583
_reflns_number_total             3416
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3416
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0416P)²+1.4751P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.1033
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C17(H17), C10(H10), C12(H12), C11(H11), C1(H1), C5(H5), C4(H4),
 C2(H2), C3(H3)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.37256(9) 0.67754(7) 0.45464(5) 0.0229(3) Uani 1 1 d . . . . .
O1 O 0.40317(9) 0.73917(7) 0.55650(5) 0.0239(3) Uani 1 1 d . . . . .
O3 O 0.59975(10) 0.74044(8) 0.57601(5) 0.0282(3) Uani 1 1 d . . . . .
N1 N 0.50370(11) 0.60144(9) 0.57547(6) 0.0208(3) Uani 1 1 d . . . . .
C8 C 0.32043(14) 0.68974(11) 0.51521(7) 0.0229(3) Uani 1 1 d . . . . .
H8 H 0.243574 0.725133 0.511041 0.027 Uiso 1 1 calc R U . . .
C9 C 0.29597(13) 0.59706(11) 0.54317(7) 0.0210(3) Uani 1 1 d . . . . .
C14 C 0.39337(13) 0.55290(11) 0.57249(7) 0.0202(3) Uani 1 1 d . . . . .
C13 C 0.37966(14) 0.46405(11) 0.59691(7) 0.0233(3) Uani 1 1 d . . . . .
H13 H 0.445179 0.433513 0.617100 0.028 Uiso 1 1 calc R U . . .
C16 C 0.61763(14) 0.55242(11) 0.58742(7) 0.0229(3) Uani 1 1 d . . . . .
H16A H 0.681160 0.579477 0.559919 0.027 Uiso 1 1 calc R U . . .
H16B H 0.607971 0.486890 0.574936 0.027 Uiso 1 1 calc R U . . .
C6 C 0.43712(14) 0.74179(11) 0.35477(8) 0.0236(3) Uani 1 1 d . . . . .
C15 C 0.50911(14) 0.69506(11) 0.56923(7) 0.0218(3) Uani 1 1 d . . . . .
C17 C 0.65752(14) 0.55698(11) 0.65643(7) 0.0243(4) Uani 1 1 d . . . . .
H17 H 0.599424 0.574617 0.687574 0.029 Uiso 1 1 calc R U . . .
C19 C 0.76785(14) 0.53819(11) 0.67699(7) 0.0253(4) Uani 1 1 d . . . . .
C10 C 0.18542(14) 0.55297(11) 0.53883(7) 0.0253(4) Uani 1 1 d . . . . .
H10 H 0.119195 0.583591 0.519382 0.030 Uiso 1 1 calc R U . . .
C12 C 0.26881(15) 0.42083(11) 0.59130(7) 0.0262(4) Uani 1 1 d . . . . .
H12 H 0.259460 0.359873 0.607387 0.031 Uiso 1 1 calc R U . . .
C11 C 0.17138(15) 0.46423(12) 0.56284(8) 0.0277(4) Uani 1 1 d . . . . .
H11 H 0.095961 0.433666 0.559805 0.033 Uiso 1 1 calc R U . . .
C7 C 0.39324(15) 0.76364(11) 0.42121(8) 0.0263(4) Uani 1 1 d . . . . .
H7A H 0.454037 0.800829 0.444412 0.032 Uiso 1 1 calc R U . . .
H7B H 0.317668 0.799674 0.418932 0.032 Uiso 1 1 calc R U . . .
C1 C 0.54828(15) 0.77254(12) 0.33351(9) 0.0312(4) Uani 1 1 d . . . . .
H1 H 0.598770 0.806506 0.361742 0.037 Uiso 1 1 calc R U . . .
C18 C 0.86826(15) 0.50903(12) 0.63308(8) 0.0309(4) Uani 1 1 d . . . . .
H18A H 0.875045 0.441580 0.633389 0.046 Uiso 1 1 calc R U . . .
H18B H 0.944037 0.536286 0.647903 0.046 Uiso 1 1 calc R U . . .
H18C H 0.851142 0.530229 0.589325 0.046 Uiso 1 1 calc R U . . .
C5 C 0.36526(16) 0.69100(12) 0.31338(8) 0.0314(4) Uani 1 1 d . . . . .
H5 H 0.289061 0.669260 0.327475 0.038 Uiso 1 1 calc R U . . .
C4 C 0.40399(19) 0.67182(14) 0.25162(9) 0.0407(5) Uani 1 1 d . . . . .
H4 H 0.354791 0.636364 0.223626 0.049 Uiso 1 1 calc R U . . .
C2 C 0.58642(18) 0.75421(13) 0.27151(10) 0.0408(5) Uani 1 1 d . . . . .
H2 H 0.662396 0.776130 0.257203 0.049 Uiso 1 1 calc R U . . .
C20 C 0.80102(17) 0.54217(14) 0.74705(9) 0.0386(5) Uani 1 1 d . . . . .
H20A H 0.858816 0.592267 0.754067 0.058 Uiso 1 1 calc R U . . .
H20B H 0.837258 0.483358 0.759971 0.058 Uiso 1 1 calc R U . . .
H20C H 0.728584 0.553490 0.772705 0.058 Uiso 1 1 calc R U . . .
C3 C 0.5142(2) 0.70420(13) 0.23062(9) 0.0439(5) Uani 1 1 d . . . . .
H3 H 0.540010 0.691935 0.187976 0.053 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
O2 C8 1.3989(18) . ?
O2 C7 1.4467(19) . ?
O1 C8 1.4484(18) . ?
O1 C15 1.3656(18) . ?
O3 C15 1.2111(18) . ?
N1 C14 1.4148(19) . ?
N1 C16 1.4728(19) . ?
N1 C15 1.364(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.488(2) . ?
C9 C14 1.398(2) . ?
C9 C10 1.388(2) . ?
C14 C13 1.392(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.387(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.505(2) . ?
C6 C7 1.501(2) . ?
C6 C1 1.386(2) . ?
C6 C5 1.386(2) . ?
C17 H17 0.9500 . ?
C17 C19 1.327(2) . ?
C19 C18 1.503(2) . ?
C19 C20 1.506(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.385(2) . ?
C11 H11 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C1 H1 0.9500 . ?
C1 C2 1.384(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C5 H5 0.9500 . ?
C5 C4 1.384(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.382(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.376(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C3 H3 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
C8 O2 C7 112.99(11) . . ?
C15 O1 C8 115.55(12) . . ?
C14 N1 C16 120.86(12) . . ?
C15 N1 C14 121.89(13) . . ?
C15 N1 C16 117.23(12) . . ?
O2 C8 O1 109.55(12) . . ?
O2 C8 H8 109.9 . . ?
O2 C8 C9 108.32(12) . . ?
O1 C8 H8 109.9 . . ?
O1 C8 C9 109.24(12) . . ?
C9 C8 H8 109.9 . . ?
C14 C9 C8 116.24(13) . . ?
C10 C9 C8 123.46(14) . . ?
C10 C9 C14 120.24(15) . . ?
C9 C14 N1 117.58(14) . . ?
C13 C14 N1 122.56(14) . . ?
C13 C14 C9 119.85(14) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 C14 118.93(15) . . ?
C12 C13 H13 120.5 . . ?
N1 C16 H16A 108.9 . . ?
N1 C16 H16B 108.9 . . ?
N1 C16 C17 113.16(12) . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C1 C6 C7 121.09(15) . . ?
C1 C6 C5 119.05(16) . . ?
C5 C6 C7 119.85(15) . . ?
O3 C15 O1 119.06(14) . . ?
O3 C15 N1 124.43(14) . . ?
N1 C15 O1 116.48(13) . . ?
C16 C17 H17 117.6 . . ?
C19 C17 C16 124.83(14) . . ?
C19 C17 H17 117.6 . . ?
C17 C19 C18 123.19(15) . . ?
C17 C19 C20 122.07(15) . . ?
C18 C19 C20 114.72(14) . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.15(15) . . ?
C11 C10 H10 119.9 . . ?
C13 C12 H12 119.1 . . ?
C11 C12 C13 121.71(15) . . ?
C11 C12 H12 119.1 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.11(15) . . ?
C12 C11 H11 120.4 . . ?
O2 C7 C6 108.26(12) . . ?
O2 C7 H7A 110.0 . . ?
O2 C7 H7B 110.0 . . ?
C6 C7 H7A 110.0 . . ?
C6 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
C6 C1 H1 119.7 . . ?
C2 C1 C6 120.61(17) . . ?
C2 C1 H1 119.7 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.32(17) . . ?
C4 C5 H5 119.8 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.08(18) . . ?
C3 C4 H4 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.93(18) . . ?
C3 C2 H2 120.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 119.99(18) . . ?
C2 C3 H3 120.0 . . ?

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
O2 C8 C9 C14 81.63(16) . . . . ?
O2 C8 C9 C10 -95.54(17) . . . . ?
O1 C8 C9 C14 -37.65(17) . . . . ?
O1 C8 C9 C10 145.18(14) . . . . ?
N1 C14 C13 C12 -179.17(14) . . . . ?
N1 C16 C17 C19 -163.37(15) . . . . ?
C8 O2 C7 C6 -174.28(12) . . . . ?
C8 O1 C15 O3 146.31(14) . . . . ?
C8 O1 C15 N1 -35.76(18) . . . . ?
C8 C9 C14 N1 2.77(19) . . . . ?
C8 C9 C14 C13 -176.71(13) . . . . ?
C8 C9 C10 C11 176.22(14) . . . . ?
C9 C14 C13 C12 0.3(2) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C14 N1 C16 C17 -98.55(16) . . . . ?
C14 N1 C15 O1 -3.4(2) . . . . ?
C14 N1 C15 O3 174.42(14) . . . . ?
C14 C9 C10 C11 -0.8(2) . . . . ?
C14 C13 C12 C11 -0.9(2) . . . . ?
C13 C12 C11 C10 0.6(2) . . . . ?
C16 N1 C14 C9 -161.78(13) . . . . ?
C16 N1 C14 C13 17.7(2) . . . . ?
C16 N1 C15 O1 178.35(12) . . . . ?
C16 N1 C15 O3 -3.8(2) . . . . ?
C16 C17 C19 C18 -0.3(3) . . . . ?
C16 C17 C19 C20 -178.66(16) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
C6 C5 C4 C3 -0.8(3) . . . . ?
C15 O1 C8 O2 -63.03(16) . . . . ?
C15 O1 C8 C9 55.48(16) . . . . ?
C15 N1 C14 C9 20.0(2) . . . . ?
C15 N1 C14 C13 -160.52(14) . . . . ?
C15 N1 C16 C17 79.74(17) . . . . ?
C10 C9 C14 N1 -179.96(13) . . . . ?
C10 C9 C14 C13 0.6(2) . . . . ?
C7 O2 C8 O1 -64.60(15) . . . . ?
C7 O2 C8 C9 176.33(12) . . . . ?
C7 C6 C1 C2 -178.16(15) . . . . ?
C7 C6 C5 C4 178.88(16) . . . . ?
C1 C6 C7 O2 -120.33(15) . . . . ?
C1 C6 C5 C4 -0.3(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C5 C6 C7 O2 60.47(19) . . . . ?
C5 C6 C1 C2 1.0(2) . . . . ?
C5 C4 C3 C2 1.1(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
