# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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. 
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#######################################################################

data_mo_ia0165_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2118729'
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-01-14 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 H23 N O3'
_chemical_formula_weight         349.41

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.2069(3)
_cell_length_b                   26.8100(11)
_cell_length_c                   8.7494(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.943(2)
_cell_angle_gamma                90
_cell_volume                     1851.06(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5985
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      28.50

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.539
_exptl_crystal_size_mid          0.460
_exptl_crystal_size_min          0.153
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6788
_exptl_absorpt_correction_T_max  0.761
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            29640
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.519
_diffrn_reflns_theta_max         30.700
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5740
_reflns_number_gt                3827
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0672P)²+0.3135P] 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         5740
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1491
_refine_ls_wR_factor_gt          0.1295
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
O1 O 0.59596(15) 0.37208(4) 0.94695(15) 0.0688(3) Uani 1 1 d . . . . .
N1 N 0.03166(13) 0.33851(4) 0.46465(13) 0.0412(2) Uani 1 1 d . . . . .
C1 C 0.56623(17) 0.41195(5) 0.88161(17) 0.0441(3) Uani 1 1 d . . . . .
O2 O 0.05187(11) 0.38938(3) 0.41686(11) 0.0439(2) Uani 1 1 d . . . . .
C2 C 0.42817(15) 0.42391(5) 0.73517(15) 0.0383(3) Uani 1 1 d . . . . .
O3 O -0.2564(2) 0.22178(6) 0.3362(3) 0.1184(7) Uani 1 1 d . . . . .
C3 C 0.30200(16) 0.39303(5) 0.64777(15) 0.0403(3) Uani 1 1 d . . . . .
H3 H 0.295846 0.359604 0.674094 0.048 Uiso 1 1 calc R U . . .
C4 C 0.18489(15) 0.41425(5) 0.51883(15) 0.0379(3) Uani 1 1 d . . . . .
C5 C 0.19497(17) 0.46423(5) 0.48060(16) 0.0439(3) Uani 1 1 d . . . . .
H5 H 0.114784 0.477581 0.393656 0.053 Uiso 1 1 calc R U . . .
C6 C 0.32262(18) 0.49446(5) 0.57002(17) 0.0462(3) Uani 1 1 d . . . . .
H6 H 0.329096 0.527862 0.543610 0.055 Uiso 1 1 calc R U . . .
C7 C 0.43963(15) 0.47418(5) 0.69860(15) 0.0389(3) Uani 1 1 d . . . . .
C8 C 0.58246(15) 0.49673(5) 0.82008(15) 0.0401(3) Uani 1 1 d . . . . .
C9 C 0.64111(19) 0.54510(6) 0.84099(18) 0.0503(3) Uani 1 1 d . . . . .
H9 H 0.592127 0.569869 0.768464 0.060 Uiso 1 1 calc R U . . .
C10 C 0.7754(2) 0.55604(6) 0.97315(19) 0.0550(4) Uani 1 1 d . . . . .
H10 H 0.815567 0.588595 0.989367 0.066 Uiso 1 1 calc R U . . .
C11 C 0.84930(19) 0.51969(6) 1.07979(19) 0.0553(4) Uani 1 1 d . . . . .
H11 H 0.939341 0.527895 1.166801 0.066 Uiso 1 1 calc R U . . .
C12 C 0.79191(18) 0.47094(6) 1.05986(18) 0.0512(3) Uani 1 1 d . . . . .
H12 H 0.841973 0.446245 1.132185 0.061 Uiso 1 1 calc R U . . .
C13 C 0.65831(16) 0.46011(5) 0.92957(16) 0.0419(3) Uani 1 1 d . . . . .
C14 C 0.06139(18) 0.30639(5) 0.33564(18) 0.0522(4) Uani 1 1 d . . . . .
C15 C 0.0240(2) 0.25274(6) 0.3768(3) 0.0735(5) Uani 1 1 d . . . . .
H15A H 0.026579 0.230954 0.288937 0.088 Uiso 1 1 calc R U . . .
H15B H 0.111687 0.241796 0.469456 0.088 Uiso 1 1 calc R U . . .
C16 C -0.1435(2) 0.24851(6) 0.4094(3) 0.0760(6) Uani 1 1 d . . . . .
C17 C -0.1607(2) 0.28227(7) 0.5399(2) 0.0720(5) Uani 1 1 d . . . . .
H17A H -0.078035 0.272913 0.638118 0.086 Uiso 1 1 calc R U . . .
H17B H -0.272650 0.278312 0.555129 0.086 Uiso 1 1 calc R U . . .
C18 C -0.13387(18) 0.33713(6) 0.50238(18) 0.0500(3) Uani 1 1 d . . . . .
C19 C 0.2496(2) 0.31073(8) 0.3463(3) 0.0760(6) Uani 1 1 d . . . . .
H19A H 0.277960 0.287272 0.274724 0.114 Uiso 1 1 calc R U . . .
H19B H 0.315305 0.303706 0.452967 0.114 Uiso 1 1 calc R U . . .
H19C H 0.273788 0.343934 0.317743 0.114 Uiso 1 1 calc R U . . .
C20 C -0.0410(2) 0.31945(7) 0.1667(2) 0.0699(5) Uani 1 1 d . . . . .
H20A H 0.000416 0.300484 0.092118 0.105 Uiso 1 1 calc R U . . .
H20B H -0.029478 0.354406 0.148265 0.105 Uiso 1 1 calc R U . . .
H20C H -0.158209 0.311672 0.153525 0.105 Uiso 1 1 calc R U . . .
C21 C -0.1139(3) 0.36814(9) 0.6520(2) 0.0745(5) Uani 1 1 d . . . . .
H21A H -0.100329 0.402619 0.628550 0.112 Uiso 1 1 calc R U . . .
H21B H -0.015908 0.357023 0.732678 0.112 Uiso 1 1 calc R U . . .
H21C H -0.212832 0.364350 0.689323 0.112 Uiso 1 1 calc R U . . .
C22 C -0.28721(19) 0.35611(7) 0.3722(2) 0.0640(4) Uani 1 1 d . . . . .
H22A H -0.258926 0.387103 0.330758 0.096 Uiso 1 1 calc R U . . .
H22B H -0.380993 0.361148 0.416173 0.096 Uiso 1 1 calc R U . . .
H22C H -0.317683 0.331973 0.288086 0.096 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 C1 1.2050(17) . ?
N1 O2 1.4494(13) . ?
N1 C18 1.4840(19) . ?
N1 C14 1.4921(19) . ?
C1 C2 1.4936(18) . ?
C1 C13 1.4968(19) . ?
O2 C4 1.3774(14) . ?
C2 C3 1.3811(17) . ?
C2 C7 1.3944(17) . ?
O3 C16 1.207(2) . ?
C3 C4 1.3874(17) . ?
C4 C5 1.3890(18) . ?
C5 C6 1.3842(18) . ?
C6 C7 1.3747(18) . ?
C7 C8 1.4781(17) . ?
C8 C9 1.3780(19) . ?
C8 C13 1.3933(19) . ?
C9 C10 1.392(2) . ?
C10 C11 1.370(2) . ?
C11 C12 1.384(2) . ?
C12 C13 1.3782(19) . ?
C14 C19 1.526(2) . ?
C14 C20 1.527(2) . ?
C14 C15 1.534(2) . ?
C15 C16 1.483(3) . ?
C16 C17 1.493(3) . ?
C17 C18 1.536(2) . ?
C18 C21 1.521(2) . ?
C18 C22 1.534(2) . ?

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
O2 N1 C18 105.78(10) . . ?
O2 N1 C14 105.63(10) . . ?
C18 N1 C14 120.25(11) . . ?
O1 C1 C2 127.19(13) . . ?
O1 C1 C13 127.69(13) . . ?
C2 C1 C13 105.12(11) . . ?
C4 O2 N1 113.69(9) . . ?
C3 C2 C7 122.68(12) . . ?
C3 C2 C1 128.54(12) . . ?
C7 C2 C1 108.74(11) . . ?
C2 C3 C4 116.80(12) . . ?
O2 C4 C3 125.24(11) . . ?
O2 C4 C5 113.58(11) . . ?
C3 C4 C5 121.18(11) . . ?
C6 C5 C4 120.97(12) . . ?
C7 C6 C5 118.76(12) . . ?
C6 C7 C2 119.61(11) . . ?
C6 C7 C8 131.64(12) . . ?
C2 C7 C8 108.69(11) . . ?
C9 C8 C13 119.87(12) . . ?
C9 C8 C7 131.26(13) . . ?
C13 C8 C7 108.82(11) . . ?
C8 C9 C10 118.46(14) . . ?
C11 C10 C9 121.15(14) . . ?
C10 C11 C12 120.94(14) . . ?
C13 C12 C11 117.98(14) . . ?
C12 C13 C8 121.60(13) . . ?
C12 C13 C1 129.74(13) . . ?
C8 C13 C1 108.62(11) . . ?
N1 C14 C19 106.44(12) . . ?
N1 C14 C20 116.05(12) . . ?
C19 C14 C20 108.66(16) . . ?
N1 C14 C15 106.20(14) . . ?
C19 C14 C15 108.75(14) . . ?
C20 C14 C15 110.48(14) . . ?
C16 C15 C14 111.87(14) . . ?
O3 C16 C15 124.1(2) . . ?
O3 C16 C17 123.1(2) . . ?
C15 C16 C17 112.84(14) . . ?
C16 C17 C18 111.57(15) . . ?
N1 C18 C21 106.80(12) . . ?
N1 C18 C22 116.16(13) . . ?
C21 C18 C22 109.29(15) . . ?
N1 C18 C17 105.36(13) . . ?
C21 C18 C17 109.10(15) . . ?
C22 C18 C17 109.88(13) . . ?

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.035



