# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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data_aks028_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc2bvfpb
_database_code_depnum_ccdc_archive 'CCDC 2170362'
loop_
_audit_author_name
_audit_author_address
'Avijit Maity'
;University of Hyderabad
India
;
_audit_update_record             
;
2024-05-27 deposited with the CCDC.	2024-10-18 downloaded from the CCDC.
;
_audit_creation_date             2022-04-29
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H23 N O3'
_chemical_formula_sum            'C22 H23 N O3'
_chemical_formula_weight         349.41
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7695(9)
_cell_length_b                   10.1839(8)
_cell_length_c                   11.1377(10)
_cell_angle_alpha                66.757(3)
_cell_angle_beta                 79.058(4)
_cell_angle_gamma                69.275(3)
_cell_volume                     950.66(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1733 before and 0.0878 after correction.
The Ratio of minimum to maximum transmission is 0.7881.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.2
_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  0.0841
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            36799
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.608
_diffrn_reflns_theta_min         1.993
_diffrn_ambient_temperature      297.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2694
_reflns_number_total             4396
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4396
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0797
_refine_ls_restrained_S_all      1.013
_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)+(0.1700P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2372
_refine_ls_wR_factor_ref         0.2563
_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:
 C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C6(H6), C7(H7), C12(H12), C9(H9), C14(H14), C18(H18), C16(H16),
 C15(H15), C17(H17), C2(H2), C3(H3)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.45320(17) 0.42073(18) 0.77097(17) 0.0554(5) Uani 1 1 d . . . . .
N1 N -0.00184(19) 0.7859(2) 0.29974(19) 0.0474(5) Uani 1 1 d . . . . .
O1 O -0.1750(2) 0.8490(2) 0.0932(2) 0.0807(7) Uani 1 1 d . . . . .
O3 O 0.6205(2) 0.3108(2) 0.9199(2) 0.0855(8) Uani 1 1 d . . . . .
C5 C 0.1076(2) 0.7597(3) 0.3790(2) 0.0400(5) Uani 1 1 d . . . . .
C8 C 0.3200(2) 0.7032(2) 0.5520(2) 0.0410(5) Uani 1 1 d . . . . .
C13 C 0.6369(2) 0.7569(2) 0.6711(2) 0.0434(6) Uani 1 1 d . . . . .
C11 C 0.4310(2) 0.6789(2) 0.6402(2) 0.0431(6) Uani 1 1 d . . . . .
C20 C 0.5517(2) 0.3024(3) 0.8474(2) 0.0480(6) Uani 1 1 d . . . . .
C10 C 0.2005(2) 0.6161(3) 0.4393(2) 0.0471(6) Uani 1 1 d . . . . .
H10 H 0.193789 0.536228 0.422442 0.057 Uiso 1 1 calc R . . . .
C6 C 0.1254(2) 0.8761(3) 0.4055(2) 0.0454(6) Uani 1 1 d . . . . .
H6 H 0.066686 0.974294 0.366020 0.054 Uiso 1 1 calc R . . . .
C7 C 0.2279(2) 0.8479(3) 0.4885(2) 0.0454(6) Uani 1 1 d . . . . .
H7 H 0.236612 0.928173 0.503414 0.054 Uiso 1 1 calc R . . . .
C12 C 0.5247(2) 0.7596(3) 0.5973(3) 0.0477(6) Uani 1 1 d . . . . .
H12 H 0.518253 0.825122 0.510680 0.057 Uiso 1 1 calc R . . . .
C9 C 0.3027(2) 0.5887(3) 0.5239(3) 0.0497(6) Uani 1 1 d . . . . .
H9 H 0.361711 0.490630 0.563173 0.060 Uiso 1 1 calc R . . . .
C14 C 0.7796(2) 0.7427(3) 0.6168(2) 0.0484(6) Uani 1 1 d . . . . .
H14 H 0.802593 0.738400 0.533223 0.058 Uiso 1 1 calc R . . . .
C18 C 0.6054(2) 0.7709(3) 0.7935(2) 0.0502(6) Uani 1 1 d . . . . .
H18 H 0.510062 0.784076 0.830638 0.060 Uiso 1 1 calc R . . . .
C19 C 0.4283(2) 0.5683(3) 0.7785(2) 0.0478(6) Uani 1 1 d . . . . .
H19 H 0.507286 0.562639 0.824810 0.057 Uiso 1 1 calc R . . . .
C16 C 0.8551(3) 0.7460(3) 0.8078(3) 0.0549(7) Uani 1 1 d . . . . .
H16 H 0.928189 0.740393 0.853936 0.066 Uiso 1 1 calc R . . . .
C15 C 0.8878(2) 0.7349(3) 0.6860(3) 0.0541(7) Uani 1 1 d . . . . .
H15 H 0.983364 0.721947 0.649620 0.065 Uiso 1 1 calc R . . . .
C17 C 0.7139(3) 0.7654(3) 0.8608(3) 0.0537(6) Uani 1 1 d . . . . .
H17 H 0.690884 0.774934 0.942525 0.064 Uiso 1 1 calc R . . . .
C21 C 0.5613(3) 0.1610(3) 0.8309(3) 0.0630(7) Uani 1 1 d . . . . .
H21A H 0.470319 0.139126 0.861858 0.094 Uiso 1 1 calc GR . . . .
H21B H 0.639327 0.079776 0.880213 0.094 Uiso 1 1 calc GR . . . .
H21C H 0.580375 0.173177 0.739963 0.094 Uiso 1 1 calc GR . . . .
C22 C 0.2843(3) 0.6071(3) 0.8543(3) 0.0609(7) Uani 1 1 d . . . . .
H22A H 0.207037 0.611008 0.809868 0.091 Uiso 1 1 calc GR . . . .
H22B H 0.265630 0.703182 0.860935 0.091 Uiso 1 1 calc GR . . . .
H22C H 0.288441 0.531885 0.940451 0.091 Uiso 1 1 calc GR . . . .
C1 C -0.0640(4) 0.9379(3) 0.2102(3) 0.0797(10) Uani 1 1 d . . . . .
H1A H 0.008133 0.963949 0.139750 0.096 Uiso 1 1 calc R . . . .
H1B H -0.088626 1.007394 0.256226 0.096 Uiso 1 1 calc R . . . .
C4 C 0.0165(3) 0.6765(4) 0.2403(4) 0.0843(11) Uani 1 1 d . . . . .
H4A H 0.044982 0.576156 0.305787 0.101 Uiso 1 1 calc R . . . .
H4B H 0.094409 0.683125 0.171786 0.101 Uiso 1 1 calc R . . . .
C2 C -0.1989(4) 0.9529(4) 0.1539(4) 0.0939(12) Uani 1 1 d . . . . .
H2 H -0.289188 1.023854 0.158896 0.113 Uiso 1 1 calc R . . . .
C3 C -0.1223(4) 0.7023(4) 0.1832(4) 0.1011(14) Uani 1 1 d . . . . .
H3 H -0.168294 0.629350 0.205063 0.121 Uiso 1 1 calc R . . . .


_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 C20 1.335(3) . ?
O2 C19 1.469(3) . ?
N1 C5 1.402(2) . ?
N1 C1 1.451(3) . ?
N1 C4 1.452(3) . ?
O1 C2 1.400(4) . ?
O1 C3 1.404(4) . ?
O3 C20 1.188(3) . ?
C5 C10 1.389(3) . ?
C5 C6 1.402(3) . ?
C8 C11 1.491(3) . ?
C8 C7 1.401(3) . ?
C8 C9 1.390(3) . ?
C13 C12 1.477(3) . ?
C13 C14 1.392(3) . ?
C13 C18 1.392(3) . ?
C11 C12 1.341(3) . ?
C11 C19 1.510(3) . ?
C20 C21 1.491(3) . ?
C10 C9 1.384(3) . ?
C6 C7 1.370(3) . ?
C14 C15 1.384(3) . ?
C18 C17 1.384(3) . ?
C19 C22 1.506(3) . ?
C16 C15 1.374(3) . ?
C16 C17 1.372(3) . ?
C1 C2 1.499(4) . ?
C4 C3 1.502(4) . ?

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 C19 117.87(17) . . ?
C5 N1 C1 118.16(18) . . ?
C5 N1 C4 118.04(18) . . ?
C1 N1 C4 111.1(2) . . ?
C2 O1 C3 109.8(3) . . ?
C10 C5 N1 121.69(18) . . ?
C10 C5 C6 116.54(19) . . ?
C6 C5 N1 121.7(2) . . ?
C7 C8 C11 120.61(18) . . ?
C9 C8 C11 123.7(2) . . ?
C9 C8 C7 115.62(19) . . ?
C14 C13 C12 119.6(2) . . ?
C18 C13 C12 122.53(19) . . ?
C18 C13 C14 117.8(2) . . ?
C8 C11 C19 118.06(18) . . ?
C12 C11 C8 119.7(2) . . ?
C12 C11 C19 122.12(19) . . ?
O2 C20 C21 111.3(2) . . ?
O3 C20 O2 123.4(2) . . ?
O3 C20 C21 125.2(2) . . ?
C9 C10 C5 121.79(19) . . ?
C7 C6 C5 121.2(2) . . ?
C6 C7 C8 122.78(19) . . ?
C11 C12 C13 127.8(2) . . ?
C10 C9 C8 122.1(2) . . ?
C15 C14 C13 120.7(2) . . ?
C17 C18 C13 120.9(2) . . ?
O2 C19 C11 107.55(17) . . ?
O2 C19 C22 107.84(18) . . ?
C22 C19 C11 113.29(19) . . ?
C17 C16 C15 119.5(2) . . ?
C16 C15 C14 120.6(2) . . ?
C16 C17 C18 120.4(2) . . ?
N1 C1 C2 111.2(3) . . ?
N1 C4 C3 111.4(2) . . ?
O1 C2 C1 113.1(3) . . ?
O1 C3 C4 112.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
