# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_LP18071_XPREP_a
_database_code_depnum_ccdc_archive 'CCDC 2064588'
loop_
_audit_author_name
_audit_author_address
'Lukas Pfeifer'
;Ecole Polytechnique Federale de Lausanne
Switzerland
;
_audit_update_record             
;
2021-02-23 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H23 N O3'
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_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, 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                   17.9980(5)
_cell_length_b                   9.6252(2)
_cell_length_c                   20.8083(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3604.71(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5292
_cell_measurement_theta_min      4.25
_cell_measurement_theta_max      79.86


_exptl_crystal_description       block
_exptl_crystal_colour            clear_light_yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.683
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6876
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_process_details   'SADABS 2016/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker PHOTON II 14 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            80118
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_av_R_equivalents  0.1135
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.249
_diffrn_reflns_theta_max         80.240
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3928
_reflns_number_gt                3173
_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 V2019.1-0'
_computing_cell_refinement       'Bruker SAINT 8.40A'
_computing_data_reduction        'Bruker SAINT 8.40A'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.0443P)²+1.2878P] 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         3928
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.0926
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_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 0.74853(5) 0.72229(11) 0.65521(4) 0.0261(2) Uani 1 1 d . . . . .
N1 N 0.37812(6) 0.11445(12) 0.60636(5) 0.0239(2) Uani 1 1 d . . . . .
C1 C 0.48382(7) 0.41853(14) 0.64837(6) 0.0207(3) Uani 1 1 d . . . . .
O2 O 0.72064(5) 0.57951(10) 0.54710(4) 0.0229(2) Uani 1 1 d . . . . .
C2 C 0.43921(8) 0.50724(14) 0.69523(6) 0.0238(3) Uani 1 1 d . . . . .
H2 H 0.403588 0.448603 0.720223 0.029 Uiso 1 1 calc R U . . .
O3 O 0.32608(5) 0.31463(10) 0.64689(5) 0.0262(2) Uani 1 1 d . . . . .
C3 C 0.50114(8) 0.56501(15) 0.73956(6) 0.0262(3) Uani 1 1 d . . . . .
H3A H 0.488001 0.658181 0.756203 0.031 Uiso 1 1 calc R U . . .
H3AB H 0.510537 0.501866 0.776232 0.031 Uiso 1 1 calc R U . . .
C4 C 0.56756(8) 0.57208(14) 0.69546(6) 0.0223(3) Uani 1 1 d . . . . .
C5 C 0.63071(7) 0.65206(14) 0.70276(6) 0.0232(3) Uani 1 1 d . . . . .
H5 H 0.638062 0.706571 0.740281 0.028 Uiso 1 1 calc R U . . .
C6 C 0.68351(7) 0.65074(14) 0.65350(6) 0.0218(3) Uani 1 1 d . . . . .
C7 C 0.66979(7) 0.57416(14) 0.59695(6) 0.0208(3) Uani 1 1 d . . . . .
C8 C 0.60675(7) 0.49207(13) 0.58942(6) 0.0199(3) Uani 1 1 d . . . . .
C9 C 0.55644(7) 0.48699(13) 0.64169(6) 0.0203(3) Uani 1 1 d . . . . .
C10 C 0.39841(8) 0.62468(16) 0.66068(7) 0.0311(3) Uani 1 1 d . . . . .
H10A H 0.434485 0.683483 0.638221 0.047 Uiso 1 1 calc R U . . .
H10B H 0.371112 0.680653 0.692152 0.047 Uiso 1 1 calc R U . . .
H10C H 0.363461 0.585237 0.629517 0.047 Uiso 1 1 calc R U . . .
C11 C 0.76004(8) 0.81392(16) 0.70861(7) 0.0297(3) Uani 1 1 d . . . . .
H11A H 0.808741 0.858620 0.704598 0.045 Uiso 1 1 calc R U . . .
H11B H 0.758140 0.760680 0.748721 0.045 Uiso 1 1 calc R U . . .
H11C H 0.721107 0.885095 0.709012 0.045 Uiso 1 1 calc R U . . .
C12 C 0.72216(8) 0.71147(15) 0.51477(7) 0.0276(3) Uani 1 1 d . . . . .
H12A H 0.755289 0.705856 0.477484 0.041 Uiso 1 1 calc R U . . .
H12B H 0.740310 0.783037 0.544361 0.041 Uiso 1 1 calc R U . . .
H12C H 0.671909 0.735474 0.500422 0.041 Uiso 1 1 calc R U . . .
C13 C 0.59178(8) 0.42648(14) 0.52492(6) 0.0229(3) Uani 1 1 d . . . . .
H13A H 0.598841 0.495815 0.490974 0.034 Uiso 1 1 calc R U . . .
H13B H 0.540558 0.392038 0.523674 0.034 Uiso 1 1 calc R U . . .
H13C H 0.626203 0.348952 0.518175 0.034 Uiso 1 1 calc R U . . .
C14 C 0.46055(7) 0.29307(14) 0.62613(6) 0.0207(3) Uani 1 1 d . . . . .
C15 C 0.38081(7) 0.24829(14) 0.62953(6) 0.0221(3) Uani 1 1 d . . . . .
C16 C 0.44955(7) 0.06517(14) 0.59231(6) 0.0221(3) Uani 1 1 d . . . . .
C17 C 0.46963(8) -0.06831(15) 0.57512(7) 0.0259(3) Uani 1 1 d . . . . .
H17 H 0.433237 -0.136998 0.565954 0.031 Uiso 1 1 calc R U . . .
C18 C 0.54505(8) -0.09832(15) 0.57174(7) 0.0285(3) Uani 1 1 d . . . . .
H18 H 0.560543 -0.189578 0.560664 0.034 Uiso 1 1 calc R U . . .
C19 C 0.59827(8) 0.00296(15) 0.58431(7) 0.0273(3) Uani 1 1 d . . . . .
H19 H 0.649520 -0.020219 0.582297 0.033 Uiso 1 1 calc R U . . .
C20 C 0.57700(8) 0.13834(15) 0.59984(6) 0.0235(3) Uani 1 1 d . . . . .
H20 H 0.613517 0.207164 0.608392 0.028 Uiso 1 1 calc R U . . .
C21 C 0.50179(7) 0.17160(14) 0.60268(6) 0.0209(3) Uani 1 1 d . . . . .
C22 C 0.31063(8) 0.03274(17) 0.60326(8) 0.0323(3) Uani 1 1 d . . . . .
H22A H 0.299229 0.011123 0.558304 0.049 Uiso 1 1 calc R U . . .
H22B H 0.269506 0.085661 0.622063 0.049 Uiso 1 1 calc R U . . .
H22C H 0.317492 -0.053852 0.627312 0.049 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 C6 1.3583(16) . ?
O1 C11 1.4337(16) . ?
N1 C15 1.3763(18) . ?
N1 C16 1.4011(18) . ?
N1 C22 1.4486(18) . ?
C1 C14 1.3594(19) . ?
C1 C9 1.4704(18) . ?
C1 C2 1.5247(18) . ?
O2 C7 1.3843(15) . ?
O2 C12 1.4376(16) . ?
C2 C10 1.528(2) . ?
C2 C3 1.5500(19) . ?
C2 H2 1.0000 . ?
O3 C15 1.2283(17) . ?
C3 C4 1.5086(18) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 C5 1.3810(19) . ?
C4 C9 1.4010(18) . ?
C5 C6 1.3977(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.4103(18) . ?
C7 C8 1.3915(18) . ?
C8 C9 1.4160(18) . ?
C8 C13 1.5076(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C21 1.4684(19) . ?
C14 C15 1.5001(18) . ?
C16 C17 1.382(2) . ?
C16 C21 1.4071(19) . ?
C17 C18 1.389(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.391(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.396(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.3921(19) . ?
C20 H20 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
C6 O1 C11 117.17(10) . . ?
C15 N1 C16 110.96(11) . . ?
C15 N1 C22 123.59(12) . . ?
C16 N1 C22 125.19(12) . . ?
C14 C1 C9 129.78(12) . . ?
C14 C1 C2 123.57(12) . . ?
C9 C1 C2 106.12(11) . . ?
C7 O2 C12 113.34(10) . . ?
C1 C2 C10 111.50(11) . . ?
C1 C2 C3 101.70(11) . . ?
C10 C2 C3 111.12(12) . . ?
C1 C2 H2 110.7 . . ?
C10 C2 H2 110.7 . . ?
C3 C2 H2 110.7 . . ?
C4 C3 C2 102.94(10) . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3AB 111.2 . . ?
C2 C3 H3AB 111.2 . . ?
H3A C3 H3AB 109.1 . . ?
C5 C4 C9 122.09(12) . . ?
C5 C4 C3 127.61(12) . . ?
C9 C4 C3 110.26(12) . . ?
C4 C5 C6 118.28(12) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
O1 C6 C5 124.19(12) . . ?
O1 C6 C7 115.95(11) . . ?
C5 C6 C7 119.84(12) . . ?
O2 C7 C8 118.41(11) . . ?
O2 C7 C6 119.35(12) . . ?
C8 C7 C6 122.24(12) . . ?
C7 C8 C9 117.03(11) . . ?
C7 C8 C13 118.94(11) . . ?
C9 C8 C13 123.71(12) . . ?
C4 C9 C8 120.13(12) . . ?
C4 C9 C1 108.26(11) . . ?
C8 C9 C1 131.04(11) . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C14 C21 131.66(12) . . ?
C1 C14 C15 122.27(12) . . ?
C21 C14 C15 105.70(11) . . ?
O3 C15 N1 124.16(12) . . ?
O3 C15 C14 129.18(12) . . ?
N1 C15 C14 106.62(11) . . ?
C17 C16 N1 127.50(13) . . ?
C17 C16 C21 122.81(13) . . ?
N1 C16 C21 109.55(12) . . ?
C16 C17 C18 117.51(13) . . ?
C16 C17 H17 121.2 . . ?
C18 C17 H17 121.2 . . ?
C17 C18 C19 121.15(13) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C18 C19 C20 120.58(13) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C21 C20 C19 119.41(13) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C16 118.41(13) . . ?
C20 C21 C14 133.53(12) . . ?
C16 C21 C14 107.02(11) . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.044



