# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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# Audit and citation data items may have been added by the CCDC. 
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data_mo210526a
_database_code_depnum_ccdc_archive 'CCDC 2211998'
_audit_update_record             
;
2022-10-10 deposited with the CCDC.	2022-12-06 downloaded from the CCDC.
;
_audit_creation_date             2021-05-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H23 N O'
_chemical_formula_sum            'C22 H23 N O'
_chemical_formula_weight         317.41
_chemical_absolute_configuration unk
_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   7.408(4)
_cell_length_b                   12.962(7)
_cell_length_c                   18.561(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1782.2(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1794
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.51
_cell_measurement_theta_min      2.19
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0757 before and 0.0622 after correction.
The Ratio of minimum to maximum transmission is 0.8456.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12522
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.515
_diffrn_reflns_theta_min         1.916
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.830
_reflns_number_gt                3420
_reflns_number_total             4748
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1146 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         4748
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0593P)²+0.0935P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1321
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4), C7(H7), C8(H8), C10(H10), C11(H11), C14(H14), C15(H15),
 C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 -0.7282(2) -0.04009(14) -0.61744(10) 0.0610(5) Uani 1 1 d . . . . .
H2 H -0.8037 -0.0692 -0.5924 0.092 Uiso 1 1 calc R U . . .
N1 N -0.4732(2) -0.31359(14) -0.46313(9) 0.0400(4) Uani 1 1 d . . . . .
C1 C -0.4836(3) -0.22348(17) -0.42718(12) 0.0384(5) Uani 1 1 d . . . . .
C2 C -0.5085(3) -0.12963(17) -0.46222(11) 0.0411(5) Uani 1 1 d . . . . .
H2A H -0.5131 -0.0689 -0.4356 0.049 Uiso 1 1 calc R U . . .
C3 C -0.5264(3) -0.12586(16) -0.53585(11) 0.0384(5) Uani 1 1 d . . . . .
C4 C -0.5167(3) -0.21951(17) -0.57263(12) 0.0425(5) Uani 1 1 d . . . . .
H4 H -0.5288 -0.2208 -0.6225 0.051 Uiso 1 1 calc R U . . .
C5 C -0.4892(3) -0.31054(17) -0.53529(11) 0.0390(5) Uani 1 1 d . . . . .
C6 C -0.4753(3) -0.22699(17) -0.34748(11) 0.0396(5) Uani 1 1 d . . . . .
C7 C -0.5267(3) -0.31444(19) -0.30983(13) 0.0476(5) Uani 1 1 d . . . . .
H7 H -0.5591 -0.3737 -0.3350 0.057 Uiso 1 1 calc R U . . .
C8 C -0.5305(4) -0.3148(2) -0.23558(14) 0.0555(6) Uani 1 1 d . . . . .
H8 H -0.5643 -0.3747 -0.2115 0.067 Uiso 1 1 calc R U . . .
C10 C -0.4317(4) -0.1418(2) -0.23374(14) 0.0590(7) Uani 1 1 d . . . . .
H10 H -0.4000 -0.0826 -0.2084 0.071 Uiso 1 1 calc R U . . .
C9 C -0.4853(3) -0.2284(2) -0.19609(13) 0.0533(6) Uani 1 1 d . . . . .
C11 C -0.4240(4) -0.14076(19) -0.30786(13) 0.0536(6) Uani 1 1 d . . . . .
H11 H -0.3843 -0.0818 -0.3316 0.064 Uiso 1 1 calc R U . . .
C12 C -0.4899(5) -0.2278(3) -0.11487(13) 0.0817(10) Uani 1 1 d . . . . .
H12A H -0.3731 -0.2463 -0.0965 0.123 Uiso 1 1 calc R U . . .
H12B H -0.5779 -0.2767 -0.0983 0.123 Uiso 1 1 calc R U . . .
H12C H -0.5216 -0.1601 -0.0981 0.123 Uiso 1 1 calc R U . . .
C13 C -0.4820(3) -0.41072(17) -0.57436(12) 0.0410(5) Uani 1 1 d . . . . .
C14 C -0.4050(3) -0.41806(19) -0.64220(12) 0.0481(6) Uani 1 1 d . . . . .
H14 H -0.3541 -0.3598 -0.6633 0.058 Uiso 1 1 calc R U . . .
C15 C -0.4028(4) -0.51137(19) -0.67916(13) 0.0518(6) Uani 1 1 d . . . . .
H15 H -0.3488 -0.5146 -0.7243 0.062 Uiso 1 1 calc R U . . .
C16 C -0.4791(3) -0.59935(19) -0.65018(13) 0.0504(6) Uani 1 1 d . . . . .
C17 C -0.5539(4) -0.5920(2) -0.58221(14) 0.0546(6) Uani 1 1 d . . . . .
H17 H -0.6048 -0.6503 -0.5613 0.066 Uiso 1 1 calc R U . . .
C18 C -0.5547(3) -0.49963(18) -0.54443(12) 0.0489(6) Uani 1 1 d . . . . .
H18 H -0.6046 -0.4973 -0.4985 0.059 Uiso 1 1 calc R U . . .
C19 C -0.4811(4) -0.6997(2) -0.69180(17) 0.0692(8) Uani 1 1 d . . . . .
H19A H -0.4044 -0.6937 -0.7333 0.104 Uiso 1 1 calc R U . . .
H19B H -0.6021 -0.7147 -0.7070 0.104 Uiso 1 1 calc R U . . .
H19C H -0.4380 -0.7545 -0.6615 0.104 Uiso 1 1 calc R U . . .
C20 C -0.5665(3) -0.02601(17) -0.57703(12) 0.0432(5) Uani 1 1 d . . . . .
C21 C -0.5864(4) 0.06696(18) -0.52776(14) 0.0590(7) Uani 1 1 d . . . . .
H21A H -0.6786 0.0535 -0.4926 0.089 Uiso 1 1 calc R U . . .
H21B H -0.6194 0.1263 -0.5558 0.089 Uiso 1 1 calc R U . . .
H21C H -0.4739 0.0798 -0.5037 0.089 Uiso 1 1 calc R U . . .
C22 C -0.4194(4) -0.0052(2) -0.63179(13) 0.0568(7) Uani 1 1 d . . . . .
H22A H -0.4514 0.0540 -0.6602 0.085 Uiso 1 1 calc R U . . .
H22B H -0.4059 -0.0641 -0.6627 0.085 Uiso 1 1 calc R U . . .
H22C H -0.3076 0.0079 -0.6072 0.085 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 H2 0.8200 . ?
O2 C20 1.425(3) . ?
N1 C1 1.347(3) . ?
N1 C5 1.345(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.481(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.374(3) . ?
C3 C4 1.394(3) . ?
C3 C20 1.532(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(3) . ?
C5 C13 1.488(3) . ?
C6 C7 1.385(3) . ?
C6 C11 1.391(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.378(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.380(4) . ?
C10 C11 1.377(3) . ?
C9 C12 1.508(3) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.386(3) . ?
C13 C18 1.388(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.391(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.382(4) . ?
C16 C17 1.381(4) . ?
C16 C19 1.513(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(3) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.520(3) . ?
C20 C22 1.514(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C20 O2 H2 109.5 . . ?
C5 N1 C1 117.56(19) . . ?
N1 C1 C2 122.26(19) . . ?
N1 C1 C6 117.75(19) . . ?
C2 C1 C6 119.94(19) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2A 119.7 . . ?
C2 C3 C4 116.8(2) . . ?
C2 C3 C20 123.0(2) . . ?
C4 C3 C20 120.08(19) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.8 . . ?
N1 C5 C4 122.5(2) . . ?
N1 C5 C13 117.1(2) . . ?
C4 C5 C13 120.36(19) . . ?
C7 C6 C1 121.2(2) . . ?
C7 C6 C11 117.8(2) . . ?
C11 C6 C1 121.0(2) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.8(2) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 119.2 . . ?
C7 C8 C9 121.6(2) . . ?
C9 C8 H8 119.2 . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C11 C10 C9 121.7(2) . . ?
C8 C9 C10 117.4(2) . . ?
C8 C9 C12 122.0(3) . . ?
C10 C9 C12 120.6(3) . . ?
C6 C11 H11 119.7 . . ?
C10 C11 C6 120.6(2) . . ?
C10 C11 H11 119.7 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C5 121.2(2) . . ?
C14 C13 C18 117.8(2) . . ?
C18 C13 C5 121.0(2) . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.9(2) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.4(2) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C19 121.0(2) . . ?
C17 C16 C15 117.6(2) . . ?
C17 C16 C19 121.4(2) . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.5(2) . . ?
C18 C17 H17 119.2 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.8(2) . . ?
C17 C18 H18 119.6 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 C3 108.49(17) . . ?
O2 C20 C21 109.7(2) . . ?
O2 C20 C22 105.93(19) . . ?
C21 C20 C3 112.85(19) . . ?
C22 C20 C3 110.26(19) . . ?
C22 C20 C21 109.4(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
N1 C1 C2 C3 1.0(3) . . . . ?
N1 C1 C6 C7 -25.3(3) . . . . ?
N1 C1 C6 C11 158.0(2) . . . . ?
N1 C5 C13 C14 -145.9(2) . . . . ?
N1 C5 C13 C18 35.1(3) . . . . ?
C1 N1 C5 C4 -0.4(3) . . . . ?
C1 N1 C5 C13 -178.57(18) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C1 C2 C3 C20 175.86(19) . . . . ?
C1 C6 C7 C8 -175.5(2) . . . . ?
C1 C6 C11 C10 174.3(2) . . . . ?
C2 C1 C6 C7 152.3(2) . . . . ?
C2 C1 C6 C11 -24.5(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C2 C3 C20 O2 -122.5(2) . . . . ?
C2 C3 C20 C21 -0.8(3) . . . . ?
C2 C3 C20 C22 121.9(2) . . . . ?
C3 C4 C5 N1 0.9(3) . . . . ?
C3 C4 C5 C13 179.0(2) . . . . ?
C4 C3 C20 O2 53.8(3) . . . . ?
C4 C3 C20 C21 175.5(2) . . . . ?
C4 C3 C20 C22 -61.8(3) . . . . ?
C4 C5 C13 C14 36.0(3) . . . . ?
C4 C5 C13 C18 -143.1(2) . . . . ?
C5 N1 C1 C2 -0.5(3) . . . . ?
C5 N1 C1 C6 177.0(2) . . . . ?
C5 C13 C14 C15 -178.3(2) . . . . ?
C5 C13 C18 C17 177.5(2) . . . . ?
C6 C1 C2 C3 -176.4(2) . . . . ?
C6 C7 C8 C9 0.7(4) . . . . ?
C7 C6 C11 C10 -2.6(4) . . . . ?
C7 C8 C9 C10 -1.5(4) . . . . ?
C7 C8 C9 C12 179.7(3) . . . . ?
C9 C10 C11 C6 1.7(4) . . . . ?
C11 C6 C7 C8 1.4(4) . . . . ?
C11 C10 C9 C8 0.3(4) . . . . ?
C11 C10 C9 C12 179.1(3) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C14 C13 C18 C17 -1.6(3) . . . . ?
C14 C15 C16 C17 -1.6(4) . . . . ?
C14 C15 C16 C19 178.1(2) . . . . ?
C15 C16 C17 C18 0.7(4) . . . . ?
C16 C17 C18 C13 0.8(4) . . . . ?
C18 C13 C14 C15 0.7(3) . . . . ?
C19 C16 C17 C18 -179.0(2) . . . . ?
C20 C3 C4 C5 -176.88(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
