# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_mo_d8v21393_0m
_database_code_depnum_ccdc_archive 'CCDC 2120493'
loop_
_audit_author_name
_audit_author_address
'yuan-yuan gao'
;sqnu
China
;
_audit_update_record             
;
2021-11-06 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 N O3'
_chemical_formula_weight         337.40

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      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                   8.2614(3)
_cell_length_b                   13.2824(5)
_cell_length_c                   8.9573(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.0190(10)
_cell_angle_gamma                90
_cell_volume                     923.51(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4694
_cell_measurement_theta_min      5.248
_cell_measurement_theta_max      53.709

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6986
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8924
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.624
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3570
_reflns_number_gt                3110
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_max     0.977
_reflns_Friedel_fraction_full    0.988

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0549P)²+0.0713P] 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     SHELXL
_refine_ls_extinction_coef       0.12(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1308 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.1(5)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3570
_refine_ls_number_parameters     231
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.012
_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 0.5587(2) 0.4326(2) 0.7803(2) 0.0705(6) Uani 1 1 d . . . . .
O2 O 0.0768(3) 0.6536(4) 0.7867(3) 0.1199(12) Uani 1 1 d . . . . .
O3 O -0.0277(2) 0.46569(16) 0.2401(2) 0.0640(6) Uani 1 1 d . . . . .
N1 N 0.5844(2) 0.46218(16) 0.5383(2) 0.0501(5) Uani 1 1 d . . . . .
C1 C 0.4974(3) 0.4316(2) 0.3806(3) 0.0486(6) Uani 1 1 d . . . . .
C2 C 0.5482(4) 0.4451(3) 0.2505(3) 0.0664(8) Uani 1 1 d . . . . .
H2 H 0.6461 0.4820 0.2572 0.080 Uiso 1 1 calc R U . . .
C3 C 0.4465(5) 0.4010(3) 0.1090(3) 0.0788(10) Uani 1 1 d . . . . .
H3 H 0.4755 0.4094 0.0182 0.095 Uiso 1 1 calc R U . . .
C4 C 0.3049(5) 0.3455(3) 0.1007(3) 0.0754(10) Uani 1 1 d . . . . .
H4 H 0.2407 0.3155 0.0049 0.090 Uiso 1 1 calc R U . . .
C5 C 0.2540(4) 0.3327(2) 0.2328(3) 0.0627(8) Uani 1 1 d . . . . .
H5 H 0.1572 0.2947 0.2262 0.075 Uiso 1 1 calc R U . . .
C6 C 0.3511(3) 0.3779(2) 0.3730(3) 0.0474(6) Uani 1 1 d . . . . .
C7 C 0.3342(3) 0.3770(2) 0.5355(3) 0.0477(6) Uani 1 1 d . . . . .
C8 C 0.5032(3) 0.4259(2) 0.6359(3) 0.0490(6) Uani 1 1 d . . . . .
C9 C 0.7494(4) 0.5136(3) 0.5955(4) 0.0728(9) Uani 1 1 d . . . . .
H9A H 0.7590 0.5501 0.6907 0.109 Uiso 1 1 calc R U . . .
H9B H 0.7575 0.5597 0.5158 0.109 Uiso 1 1 calc R U . . .
H9C H 0.8407 0.4651 0.6179 0.109 Uiso 1 1 calc R U . . .
C10 C 0.3219(4) 0.2713(3) 0.5979(4) 0.0709(8) Uani 1 1 d . . . . .
H10A H 0.3209 0.2756 0.7045 0.106 Uiso 1 1 calc R U . . .
H10B H 0.4194 0.2322 0.5970 0.106 Uiso 1 1 calc R U . . .
H10C H 0.2178 0.2396 0.5312 0.106 Uiso 1 1 calc R U . . .
C11 C 0.1809(3) 0.4422(2) 0.5470(3) 0.0501(6) Uani 1 1 d . . . . .
H11A H 0.0755 0.4040 0.5002 0.060 Uiso 1 1 calc R U . . .
H11B H 0.1968 0.4514 0.6586 0.060 Uiso 1 1 calc R U . . .
C12 C 0.1551(3) 0.5444(2) 0.4698(3) 0.0484(6) Uani 1 1 d . . . . .
C13 C 0.0507(3) 0.5527(2) 0.3093(3) 0.0528(6) Uani 1 1 d . . . . .
C14 C 0.0260(4) 0.6436(3) 0.2290(4) 0.0725(9) Uani 1 1 d . . . . .
H14 H -0.0411 0.6466 0.1219 0.087 Uiso 1 1 calc R U . . .
C15 C 0.1011(6) 0.7288(3) 0.3086(5) 0.0861(10) Uani 1 1 d . . . . .
H15 H 0.0868 0.7900 0.2550 0.103 Uiso 1 1 calc R U . . .
C16 C 0.1966(5) 0.7244(3) 0.4658(5) 0.0785(10) Uani 1 1 d . . . . .
H16 H 0.2429 0.7834 0.5193 0.094 Uiso 1 1 calc R U . . .
C17 C 0.2267(3) 0.6331(2) 0.5488(3) 0.0591(7) Uani 1 1 d . . . . .
C18 C 0.3301(4) 0.6368(3) 0.7231(4) 0.0696(8) Uani 1 1 d . . . . .
H18A H 0.3914 0.5735 0.7525 0.083 Uiso 1 1 calc R U . . .
H18B H 0.4157 0.6895 0.7403 0.083 Uiso 1 1 calc R U . . .
C19 C 0.2306(4) 0.6549(2) 0.8327(4) 0.0653(8) Uani 1 1 d . . . . .
C20 C 0.3353(5) 0.6722(3) 1.0039(4) 0.0834(10) Uani 1 1 d . . . . .
H20A H 0.3405 0.7430 1.0263 0.125 Uiso 1 1 calc R U . . .
H20B H 0.4498 0.6467 1.0251 0.125 Uiso 1 1 calc R U . . .
H20C H 0.2828 0.6379 1.0699 0.125 Uiso 1 1 calc R U . . .
C21 C -0.1131(4) 0.4648(4) 0.0724(3) 0.0867(11) Uani 1 1 d . . . . .
H21A H -0.0325 0.4817 0.0205 0.130 Uiso 1 1 calc R U . . .
H21B H -0.2050 0.5131 0.0442 0.130 Uiso 1 1 calc R U . . .
H21C H -0.1593 0.3989 0.0394 0.130 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 1.218(3) . ?
O2 C19 1.194(4) . ?
O3 C13 1.366(4) . ?
O3 C21 1.424(3) . ?
N1 C8 1.360(3) . ?
N1 C1 1.408(3) . ?
N1 C9 1.452(4) . ?
C1 C2 1.378(4) . ?
C1 C6 1.386(4) . ?
C2 C3 1.388(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.510(3) . ?
C7 C8 1.523(3) . ?
C7 C10 1.528(4) . ?
C7 C11 1.567(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.505(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C17 1.397(4) . ?
C12 C13 1.405(3) . ?
C13 C14 1.384(4) . ?
C14 C15 1.369(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.359(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.400(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.501(4) . ?
C18 C19 1.500(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.498(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C13 O3 C21 118.2(3) . . ?
C8 N1 C1 110.4(2) . . ?
C8 N1 C9 123.3(2) . . ?
C1 N1 C9 125.8(2) . . ?
C2 C1 C6 122.5(2) . . ?
C2 C1 N1 127.8(3) . . ?
C6 C1 N1 109.58(19) . . ?
C1 C2 C3 116.9(3) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 H2 121.5 . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 121.5(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 118.0(3) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C1 119.8(2) . . ?
C5 C6 C7 131.3(2) . . ?
C1 C6 C7 108.9(2) . . ?
C6 C7 C8 101.4(2) . . ?
C6 C7 C10 113.5(2) . . ?
C8 C7 C10 109.8(2) . . ?
C6 C7 C11 113.7(2) . . ?
C8 C7 C11 108.9(2) . . ?
C10 C7 C11 109.2(2) . . ?
O1 C8 N1 124.6(2) . . ?
O1 C8 C7 126.4(2) . . ?
N1 C8 C7 109.02(19) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C7 117.31(19) . . ?
C12 C11 H11A 108.0 . . ?
C7 C11 H11A 108.0 . . ?
C12 C11 H11B 108.0 . . ?
C7 C11 H11B 108.0 . . ?
H11A C11 H11B 107.2 . . ?
C17 C12 C13 117.3(3) . . ?
C17 C12 C11 124.0(2) . . ?
C13 C12 C11 118.8(2) . . ?
O3 C13 C14 122.6(2) . . ?
O3 C13 C12 115.4(2) . . ?
C14 C13 C12 122.0(3) . . ?
C15 C14 C13 119.4(3) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C16 C15 C14 120.2(4) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 121.5(3) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C12 C17 C16 119.6(3) . . ?
C12 C17 C18 123.1(3) . . ?
C16 C17 C18 117.3(3) . . ?
C19 C18 C17 116.2(2) . . ?
C19 C18 H18A 108.2 . . ?
C17 C18 H18A 108.2 . . ?
C19 C18 H18B 108.2 . . ?
C17 C18 H18B 108.2 . . ?
H18A C18 H18B 107.4 . . ?
O2 C19 C20 121.9(3) . . ?
O2 C19 C18 121.9(3) . . ?
C20 C19 C18 116.2(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C8 N1 C1 C2 -173.4(3) . . . . ?
C9 N1 C1 C2 -1.0(4) . . . . ?
C8 N1 C1 C6 2.8(3) . . . . ?
C9 N1 C1 C6 175.2(3) . . . . ?
C6 C1 C2 C3 -0.8(4) . . . . ?
N1 C1 C2 C3 175.0(3) . . . . ?
C1 C2 C3 C4 -1.1(5) . . . . ?
C2 C3 C4 C5 1.5(5) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 C1 -1.9(4) . . . . ?
C4 C5 C6 C7 -178.4(3) . . . . ?
C2 C1 C6 C5 2.3(4) . . . . ?
N1 C1 C6 C5 -174.2(2) . . . . ?
C2 C1 C6 C7 179.5(2) . . . . ?
N1 C1 C6 C7 3.1(3) . . . . ?
C5 C6 C7 C8 169.9(3) . . . . ?
C1 C6 C7 C8 -6.9(3) . . . . ?
C5 C6 C7 C10 52.2(4) . . . . ?
C1 C6 C7 C10 -124.6(2) . . . . ?
C5 C6 C7 C11 -73.4(4) . . . . ?
C1 C6 C7 C11 109.8(2) . . . . ?
C1 N1 C8 O1 172.9(3) . . . . ?
C9 N1 C8 O1 0.2(4) . . . . ?
C1 N1 C8 C7 -7.5(3) . . . . ?
C9 N1 C8 C7 179.9(2) . . . . ?
C6 C7 C8 O1 -171.7(3) . . . . ?
C10 C7 C8 O1 -51.4(4) . . . . ?
C11 C7 C8 O1 68.1(3) . . . . ?
C6 C7 C8 N1 8.7(3) . . . . ?
C10 C7 C8 N1 129.0(2) . . . . ?
C11 C7 C8 N1 -111.5(2) . . . . ?
C6 C7 C11 C12 -43.6(3) . . . . ?
C8 C7 C11 C12 68.7(3) . . . . ?
C10 C7 C11 C12 -171.4(2) . . . . ?
C7 C11 C12 C17 -92.4(3) . . . . ?
C7 C11 C12 C13 88.7(3) . . . . ?
C21 O3 C13 C14 11.3(4) . . . . ?
C21 O3 C13 C12 -170.3(2) . . . . ?
C17 C12 C13 O3 -175.0(2) . . . . ?
C11 C12 C13 O3 3.9(3) . . . . ?
C17 C12 C13 C14 3.4(4) . . . . ?
C11 C12 C13 C14 -177.7(2) . . . . ?
O3 C13 C14 C15 176.3(3) . . . . ?
C12 C13 C14 C15 -1.9(5) . . . . ?
C13 C14 C15 C16 -1.1(6) . . . . ?
C14 C15 C16 C17 2.6(6) . . . . ?
C13 C12 C17 C16 -1.8(4) . . . . ?
C11 C12 C17 C16 179.3(3) . . . . ?
C13 C12 C17 C18 175.4(2) . . . . ?
C11 C12 C17 C18 -3.5(4) . . . . ?
C15 C16 C17 C12 -1.1(5) . . . . ?
C15 C16 C17 C18 -178.5(3) . . . . ?
C12 C17 C18 C19 -89.6(4) . . . . ?
C16 C17 C18 C19 87.7(4) . . . . ?
C17 C18 C19 O2 9.4(6) . . . . ?
C17 C18 C19 C20 -172.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C18 H18A O1 0.97 2.29 3.243(4) 167.8 .

_refine_diff_density_max         0.148
_refine_diff_density_min         -0.115
_refine_diff_density_rms         0.023

_shelxl_version_number           2013-4

