# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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_1a_Xraystructure
_database_code_depnum_ccdc_archive 'CCDC 2371909'
loop_
_audit_author_name
_audit_author_address
'Michael Young'
;University of Toledo
United States of America
;
_audit_update_record             
;
2024-07-18 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT097_1a_Xraystructure    
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.40 eA-3
RESPONSE: There was partial disorder which was manifest in the olefin and beta aryl group, but this could not be clearly differentiated for all of the atoms in the phenyl ring, or for the remainder of the structure, so a full refinement of the disorder using a part function wasn't applied.
;
# Added during the CSD deposition process: Thursday 18 July 2024 05:10 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        
'Ethyl (Z)-4-(3-(tert-butylamino)-1-phenylprop-1-en-2-yl)benzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H27 N O2'
_chemical_formula_sum            'C22 H27 N O2'
_chemical_formula_weight         337.44

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.9849(3)
_cell_length_b                   9.8126(4)
_cell_length_c                   12.5088(5)
_cell_angle_alpha                77.534(2)
_cell_angle_beta                 79.796(2)
_cell_angle_gamma                65.7270(10)
_cell_volume                     976.79(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9986
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      33.16

_exptl_crystal_description       cubic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(SADABS; Bruker, 2017)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'fine-focus sealed tube'
_diffrn_measurement_method       'Bruker APEXIII CCD'
_diffrn_detector_area_resol_mean 'omega and phi scans'
_diffrn_reflns_number            20478
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.306
_diffrn_reflns_theta_max         33.165
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             7105
_reflns_number_gt                5406
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+(0.1412P)²+1.3231P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7105
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0919
_refine_ls_wR_factor_ref         0.2786
_refine_ls_wR_factor_gt          0.2590
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.3986(2) -0.15016(18) 0.84103(12) 0.0260(3) Uani 1 1 d . . . . .
O2 O 0.60474(18) -0.09741(17) 0.87500(11) 0.0238(3) Uani 1 1 d . . . . .
N1 N 0.71572(19) 0.27048(18) 0.33294(14) 0.0201(3) Uani 1 1 d . . . . .
C1 C 0.9836(3) 0.1402(3) 0.2467(2) 0.0351(5) Uani 1 1 d . . . . .
H00O H 0.934319 0.138680 0.183327 0.053 Uiso 1 1 calc R U . . .
H00P H 0.992069 0.050109 0.301646 0.053 Uiso 1 1 calc R U . . .
H00Q H 1.093327 0.140716 0.222700 0.053 Uiso 1 1 calc R U . . .
C5 C 0.5842(2) 0.4025(2) 0.37241(15) 0.0198(3) Uani 1 1 d . . . . .
H5 H 0.554174 0.487879 0.310622 0.024 Uiso 1 1 calc R U . . .
H00G H 0.622864 0.433546 0.428965 0.024 Uiso 1 1 calc R U . . .
C6 C 0.4354(2) 0.3671(2) 0.42103(15) 0.0187(3) Uani 1 1 d . . . . .
C7 C 0.2904(2) 0.4396(2) 0.37910(15) 0.0196(3) Uani 1 1 d . . . . .
H7 H 0.202617 0.415305 0.420302 0.024 Uiso 1 1 calc R U . . .
C8 C 0.2477(2) 0.5514(2) 0.27843(14) 0.0184(3) Uani 1 1 d . . . . .
C9 C 0.3482(2) 0.5370(2) 0.17909(15) 0.0216(4) Uani 1 1 d . . . . .
H9 H 0.449575 0.452234 0.175226 0.026 Uiso 1 1 calc R U . . .
C10 C 0.3018(3) 0.6451(3) 0.08572(16) 0.0263(4) Uani 1 1 d . . . . .
H00H H 0.372022 0.634140 0.018985 0.032 Uiso 1 1 calc R U . . .
C11 C 0.1539(3) 0.7686(3) 0.08968(18) 0.0292(4) Uani 1 1 d . . . . .
H00M H 0.123447 0.843727 0.026483 0.035 Uiso 1 1 calc R U . . .
C12 C 0.0504(3) 0.7817(3) 0.18701(19) 0.0300(4) Uani 1 1 d . . . . .
H00N H -0.052547 0.864783 0.189676 0.036 Uiso 1 1 calc R U . . .
C13 C 0.0963(2) 0.6741(2) 0.28038(17) 0.0246(4) Uani 1 1 d . . . . .
H13 H 0.024038 0.684019 0.346241 0.029 Uiso 1 1 calc R U . . .
C14 C 0.4524(2) 0.2512(2) 0.52123(15) 0.0186(3) Uani 1 1 d . . . . .
C15 C 0.3522(2) 0.1666(2) 0.54664(15) 0.0197(3) Uani 1 1 d . . . . .
H15 H 0.273674 0.183773 0.498207 0.024 Uiso 1 1 calc R U . . .
C16 C 0.3661(2) 0.0593(2) 0.64047(14) 0.0181(3) Uani 1 1 d . . . . .
H16 H 0.300191 0.001323 0.654383 0.022 Uiso 1 1 calc R U . . .
C17 C 0.4763(2) 0.0357(2) 0.71472(14) 0.0176(3) Uani 1 1 d . . . . .
C18 C 0.5783(2) 0.1170(2) 0.69061(16) 0.0224(4) Uani 1 1 d . . . . .
H00I H 0.655664 0.100037 0.739834 0.027 Uiso 1 1 calc R U . . .
C19 C 0.5666(2) 0.2224(2) 0.59494(16) 0.0211(3) Uani 1 1 d . . . . .
H00J H 0.637354 0.275773 0.579187 0.025 Uiso 1 1 calc R U . . .
C20 C 0.4871(2) -0.0794(2) 0.81468(14) 0.0178(3) Uani 1 1 d . . . . .
C21 C 0.6201(3) -0.2038(2) 0.97702(16) 0.0253(4) Uani 1 1 d . . . . .
H00K H 0.643626 -0.306129 0.962134 0.030 Uiso 1 1 calc R U . . .
H00L H 0.517101 -0.171517 1.026503 0.030 Uiso 1 1 calc R U . . .
C22 C 0.7594(3) -0.2051(3) 1.02899(17) 0.0294(4) Uani 1 1 d . . . . .
H00B H 0.862824 -0.250120 0.983936 0.044 Uiso 1 1 calc R U . . .
H00C H 0.764689 -0.264823 1.102942 0.044 Uiso 1 1 calc R U . . .
H22 H 0.741603 -0.101050 1.033946 0.044 Uiso 1 1 calc R U . . .
H1 H 0.682(4) 0.253(4) 0.270(3) 0.044 Uiso 1 1 d . U . . .
C2 C 0.8658(3) 0.4224(3) 0.2124(3) 0.0421(6) Uani 1 1 d . . . . .
H00R H 0.976286 0.421157 0.188732 0.063 Uiso 1 1 calc R U . . .
H00S H 0.798450 0.513435 0.245357 0.063 Uiso 1 1 calc R U . . .
H00T H 0.815927 0.422663 0.148742 0.063 Uiso 1 1 calc R U . . .
C3 C 0.9515(3) 0.2813(4) 0.3975(3) 0.0472(7) Uani 1 1 d . . . . .
H00U H 1.065282 0.271657 0.376294 0.071 Uiso 1 1 calc R U . . .
H00V H 0.949002 0.195755 0.454166 0.071 Uiso 1 1 calc R U . . .
H00W H 0.888297 0.376220 0.426662 0.071 Uiso 1 1 calc R U . . .
C4 C 0.8765(2) 0.2819(2) 0.29729(17) 0.0250(4) Uani 1 1 d . . . . .


_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 C20 1.219(2) . ?
O2 C20 1.337(2) . ?
O2 C21 1.451(2) . ?
N1 C5 1.459(3) . ?
N1 C4 1.477(2) . ?
C1 C4 1.524(3) . ?
C5 C6 1.511(3) . ?
C6 C7 1.341(2) . ?
C6 C14 1.482(2) . ?
C7 C8 1.472(2) . ?
C8 C9 1.397(3) . ?
C8 C13 1.399(3) . ?
C9 C10 1.392(3) . ?
C10 C11 1.384(3) . ?
C11 C12 1.390(3) . ?
C12 C13 1.389(3) . ?
C14 C19 1.403(2) . ?
C14 C15 1.415(2) . ?
C15 C16 1.383(2) . ?
C16 C17 1.393(2) . ?
C17 C18 1.403(2) . ?
C17 C20 1.480(2) . ?
C18 C19 1.390(3) . ?
C21 C22 1.504(3) . ?
C2 C4 1.527(3) . ?
C3 C4 1.523(3) . ?

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 C21 116.58(14) . . ?
C5 N1 C4 116.42(15) . . ?
N1 C5 C6 110.56(15) . . ?
C7 C6 C14 120.02(16) . . ?
C7 C6 C5 122.46(16) . . ?
C14 C6 C5 117.48(15) . . ?
C6 C7 C8 129.32(16) . . ?
C9 C8 C13 118.20(16) . . ?
C9 C8 C7 122.99(17) . . ?
C13 C8 C7 118.73(17) . . ?
C10 C9 C8 120.90(18) . . ?
C11 C10 C9 120.28(19) . . ?
C10 C11 C12 119.37(18) . . ?
C13 C12 C11 120.52(19) . . ?
C12 C13 C8 120.65(19) . . ?
C19 C14 C15 117.47(16) . . ?
C19 C14 C6 121.52(16) . . ?
C15 C14 C6 121.00(15) . . ?
C16 C15 C14 121.39(16) . . ?
C15 C16 C17 120.39(15) . . ?
C16 C17 C18 119.19(16) . . ?
C16 C17 C20 118.92(15) . . ?
C18 C17 C20 121.84(15) . . ?
C19 C18 C17 120.26(16) . . ?
C18 C19 C14 121.24(17) . . ?
O1 C20 O2 122.80(16) . . ?
O1 C20 C17 124.49(16) . . ?
O2 C20 C17 112.71(15) . . ?
O2 C21 C22 106.67(16) . . ?
N1 C4 C1 105.85(17) . . ?
N1 C4 C2 113.00(17) . . ?
C1 C4 C2 109.5(2) . . ?
N1 C4 C3 109.19(19) . . ?
C1 C4 C3 109.2(2) . . ?
C2 C4 C3 110.0(2) . . ?

_refine_diff_density_max         1.398
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.090



_exptl_crystal_recrystallization_method 'Slow evaporation'
