# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_rpr037
_database_code_depnum_ccdc_archive 'CCDC 2417394'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2025-01-16 deposited with the CCDC.	2026-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H23 N O2'
_chemical_formula_sum            'C24 H23 N O2'
_chemical_formula_weight         357.43

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   12.7517(4)
_cell_length_b                   6.1426(2)
_cell_length_c                   13.2572(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.7600(10)
_cell_angle_gamma                90
_cell_volume                     927.20(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9950
_cell_measurement_theta_min      3.73
_cell_measurement_theta_max      79.08

_exptl_crystal_description       flake
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.074
_exptl_absorpt_coefficient_mu    0.637
_shelx_estimated_absorpt_T_min   0.789
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8379
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11763
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.734
_diffrn_reflns_theta_max         79.508
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3877
_reflns_number_gt                3825
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.791
_reflns_Friedel_fraction_max     0.943
_reflns_Friedel_fraction_full    0.997

_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 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0301P)²+0.1210P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1666 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.11(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3877
_refine_ls_number_parameters     250
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0661
_refine_ls_wR_factor_gt          0.0657
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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 0.44836(9) 0.66956(18) 0.46030(8) 0.0219(2) Uani 1 1 d . . . . .
O2 O 0.32601(9) 0.24445(17) 0.38009(9) 0.0207(2) Uani 1 1 d D . . . .
H2O H 0.3958(17) 0.224(4) 0.4315(17) 0.034(5) Uiso 1 1 d D . . . .
N N 0.35422(11) 0.6494(2) 0.57258(10) 0.0205(2) Uani 1 1 d . . . . .
C1 C 0.41001(13) 0.8330(3) 0.64745(12) 0.0215(3) Uani 1 1 d . . . . .
H1A H 0.347952 0.930815 0.646652 0.026 Uiso 1 1 calc R U . . .
H1B H 0.456261 0.915886 0.617262 0.026 Uiso 1 1 calc R U . . .
C2 C 0.49007(12) 0.7704(3) 0.76859(12) 0.0218(3) Uani 1 1 d . . . . .
C3 C 0.50310(16) 0.9140(3) 0.85487(15) 0.0319(4) Uani 1 1 d . . . . .
H3 H 0.457888 1.043851 0.837544 0.038 Uiso 1 1 calc R U . . .
C4 C 0.58214(18) 0.8678(4) 0.96644(15) 0.0414(5) Uani 1 1 d . . . . .
H4 H 0.590973 0.966703 1.024826 0.050 Uiso 1 1 calc R U . . .
C5 C 0.64765(16) 0.6788(4) 0.99239(14) 0.0398(4) Uani 1 1 d . . . . .
H5 H 0.702085 0.648262 1.068401 0.048 Uiso 1 1 calc R U . . .
C6 C 0.63376(16) 0.5339(4) 0.90732(16) 0.0369(4) Uani 1 1 d . . . . .
H6 H 0.678031 0.402844 0.925136 0.044 Uiso 1 1 calc R U . . .
C7 C 0.55524(15) 0.5797(3) 0.79592(14) 0.0289(3) Uani 1 1 d . . . . .
H7 H 0.546110 0.479381 0.737980 0.035 Uiso 1 1 calc R U . . .
C11 C 0.37151(11) 0.5949(2) 0.48141(11) 0.0173(3) Uani 1 1 d . . . . .
C12 C 0.27715(11) 0.4249(2) 0.40936(11) 0.0157(3) Uani 1 1 d . . . . .
C13 C 0.22307(11) 0.3721(2) 0.48783(11) 0.0168(3) Uani 1 1 d . . . . .
C14 C 0.26881(12) 0.5139(2) 0.57995(12) 0.0197(3) Uani 1 1 d . . . . .
C15 C 0.23288(14) 0.5110(3) 0.66409(13) 0.0269(3) Uani 1 1 d . . . . .
H15 H 0.263889 0.610481 0.725503 0.032 Uiso 1 1 calc R U . . .
C16 C 0.14897(14) 0.3554(3) 0.65487(14) 0.0295(3) Uani 1 1 d . . . . .
H16 H 0.122332 0.348829 0.711178 0.035 Uiso 1 1 calc R U . . .
C17 C 0.10382(14) 0.2102(3) 0.56497(13) 0.0257(3) Uani 1 1 d . . . . .
H17 H 0.047973 0.104111 0.561247 0.031 Uiso 1 1 calc R U . . .
C18 C 0.14008(12) 0.2191(2) 0.47966(12) 0.0201(3) Uani 1 1 d . . . . .
H18 H 0.108203 0.121694 0.417376 0.024 Uiso 1 1 calc R U . . .
C21 C 0.18759(11) 0.5394(2) 0.29654(11) 0.0162(3) Uani 1 1 d . . . . .
C22 C 0.25197(13) 0.6197(3) 0.22928(12) 0.0229(3) Uani 1 1 d . . . . .
H22A H 0.194308 0.668062 0.154197 0.034 Uiso 1 1 calc R U . . .
H22B H 0.298982 0.500752 0.221448 0.034 Uiso 1 1 calc R U . . .
H22C H 0.303587 0.741528 0.269382 0.034 Uiso 1 1 calc R U . . .
C23 C 0.13549(13) 0.7399(2) 0.32617(13) 0.0225(3) Uani 1 1 d . . . . .
H23A H 0.071666 0.799126 0.257228 0.034 Uiso 1 1 calc R U . . .
H23B H 0.196714 0.850519 0.361091 0.034 Uiso 1 1 calc R U . . .
H23C H 0.104753 0.698164 0.379150 0.034 Uiso 1 1 calc R U . . .
C24 C 0.09225(11) 0.3765(2) 0.22380(11) 0.0177(3) Uani 1 1 d . . . . .
C25 C 0.11431(13) 0.2225(2) 0.15783(12) 0.0224(3) Uani 1 1 d . . . . .
H25 H 0.190596 0.213607 0.162139 0.027 Uiso 1 1 calc R U . . .
C26 C 0.02694(16) 0.0823(3) 0.08618(13) 0.0294(3) Uani 1 1 d . . . . .
H26 H 0.043440 -0.018266 0.040769 0.035 Uiso 1 1 calc R U . . .
C27 C -0.08437(16) 0.0887(3) 0.08068(13) 0.0332(4) Uani 1 1 d . . . . .
H27 H -0.143825 -0.008543 0.032588 0.040 Uiso 1 1 calc R U . . .
C28 C -0.10764(14) 0.2377(3) 0.14586(14) 0.0325(4) Uani 1 1 d . . . . .
H28 H -0.183475 0.242537 0.142816 0.039 Uiso 1 1 calc R U . . .
C29 C -0.02058(13) 0.3818(3) 0.21631(13) 0.0250(3) Uani 1 1 d . . . . .
H29 H -0.038394 0.484800 0.259789 0.030 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 C11 1.2232(18) . ?
O2 C12 1.4090(16) . ?
N C11 1.3644(18) . ?
N C14 1.4086(19) . ?
N C1 1.4583(19) . ?
C1 C2 1.514(2) . ?
C2 C7 1.387(2) . ?
C2 C3 1.394(2) . ?
C3 C4 1.393(3) . ?
C4 C5 1.380(3) . ?
C5 C6 1.384(3) . ?
C6 C7 1.390(3) . ?
C11 C12 1.5541(18) . ?
C12 C13 1.5194(18) . ?
C12 C21 1.5805(17) . ?
C13 C18 1.383(2) . ?
C13 C14 1.396(2) . ?
C14 C15 1.384(2) . ?
C15 C16 1.399(2) . ?
C16 C17 1.389(2) . ?
C17 C18 1.402(2) . ?
C21 C23 1.5319(19) . ?
C21 C24 1.5341(18) . ?
C21 C22 1.5400(19) . ?
C24 C29 1.397(2) . ?
C24 C25 1.400(2) . ?
C25 C26 1.390(2) . ?
C26 C27 1.389(3) . ?
C27 C28 1.380(3) . ?
C28 C29 1.398(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
C11 N C14 110.78(12) . . ?
C11 N C1 124.67(12) . . ?
C14 N C1 124.41(12) . . ?
N C1 C2 114.53(13) . . ?
C7 C2 C3 118.95(15) . . ?
C7 C2 C1 122.01(14) . . ?
C3 C2 C1 118.96(15) . . ?
C4 C3 C2 120.29(18) . . ?
C5 C4 C3 120.21(17) . . ?
C4 C5 C6 119.78(17) . . ?
C5 C6 C7 120.17(19) . . ?
C2 C7 C6 120.58(16) . . ?
O1 C11 N 125.19(13) . . ?
O1 C11 C12 126.14(12) . . ?
N C11 C12 108.67(11) . . ?
O2 C12 C13 114.47(12) . . ?
O2 C12 C11 112.44(11) . . ?
C13 C12 C11 100.78(11) . . ?
O2 C12 C21 108.07(10) . . ?
C13 C12 C21 112.68(10) . . ?
C11 C12 C21 108.19(11) . . ?
C18 C13 C14 119.76(13) . . ?
C18 C13 C12 131.19(13) . . ?
C14 C13 C12 109.04(12) . . ?
C15 C14 C13 122.52(13) . . ?
C15 C14 N 127.63(13) . . ?
C13 C14 N 109.85(12) . . ?
C14 C15 C16 117.15(14) . . ?
C17 C16 C15 121.27(14) . . ?
C16 C17 C18 120.48(14) . . ?
C13 C18 C17 118.80(13) . . ?
C23 C21 C24 111.89(11) . . ?
C23 C21 C22 107.27(12) . . ?
C24 C21 C22 108.86(11) . . ?
C23 C21 C12 109.09(11) . . ?
C24 C21 C12 109.57(11) . . ?
C22 C21 C12 110.13(11) . . ?
C29 C24 C25 117.46(13) . . ?
C29 C24 C21 121.94(13) . . ?
C25 C24 C21 120.54(12) . . ?
C26 C25 C24 121.38(15) . . ?
C27 C26 C25 120.29(16) . . ?
C28 C27 C26 119.25(15) . . ?
C27 C28 C29 120.55(15) . . ?
C24 C29 C28 121.04(15) . . ?

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
C11 N C1 C2 -117.06(15) . . . . ?
C14 N C1 C2 67.70(18) . . . . ?
N C1 C2 C7 33.40(19) . . . . ?
N C1 C2 C3 -149.82(14) . . . . ?
C7 C2 C3 C4 1.2(2) . . . . ?
C1 C2 C3 C4 -175.65(16) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C3 C2 C7 C6 -1.1(2) . . . . ?
C1 C2 C7 C6 175.71(15) . . . . ?
C5 C6 C7 C2 0.1(3) . . . . ?
C14 N C11 O1 -172.28(14) . . . . ?
C1 N C11 O1 11.9(2) . . . . ?
C14 N C11 C12 8.18(16) . . . . ?
C1 N C11 C12 -167.62(13) . . . . ?
O1 C11 C12 O2 48.73(19) . . . . ?
N C11 C12 O2 -131.73(12) . . . . ?
O1 C11 C12 C13 171.06(14) . . . . ?
N C11 C12 C13 -9.41(14) . . . . ?
O1 C11 C12 C21 -70.54(17) . . . . ?
N C11 C12 C21 109.00(12) . . . . ?
O2 C12 C13 C18 -53.08(19) . . . . ?
C11 C12 C13 C18 -173.98(14) . . . . ?
C21 C12 C13 C18 70.93(19) . . . . ?
O2 C12 C13 C14 128.39(12) . . . . ?
C11 C12 C13 C14 7.49(14) . . . . ?
C21 C12 C13 C14 -107.60(13) . . . . ?
C18 C13 C14 C15 -1.2(2) . . . . ?
C12 C13 C14 C15 177.57(14) . . . . ?
C18 C13 C14 N 177.96(12) . . . . ?
C12 C13 C14 N -3.31(16) . . . . ?
C11 N C14 C15 175.86(15) . . . . ?
C1 N C14 C15 -8.3(2) . . . . ?
C11 N C14 C13 -3.20(17) . . . . ?
C1 N C14 C13 172.61(13) . . . . ?
C13 C14 C15 C16 1.2(2) . . . . ?
N C14 C15 C16 -177.79(16) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C14 C13 C18 C17 -0.1(2) . . . . ?
C12 C13 C18 C17 -178.45(14) . . . . ?
C16 C17 C18 C13 1.2(2) . . . . ?
O2 C12 C21 C23 -178.58(11) . . . . ?
C13 C12 C21 C23 53.94(15) . . . . ?
C11 C12 C21 C23 -56.58(14) . . . . ?
O2 C12 C21 C24 58.62(13) . . . . ?
C13 C12 C21 C24 -68.86(14) . . . . ?
C11 C12 C21 C24 -179.39(10) . . . . ?
O2 C12 C21 C22 -61.10(14) . . . . ?
C13 C12 C21 C22 171.42(12) . . . . ?
C11 C12 C21 C22 60.89(14) . . . . ?
C23 C21 C24 C29 -17.95(18) . . . . ?
C22 C21 C24 C29 -136.33(14) . . . . ?
C12 C21 C24 C29 103.18(14) . . . . ?
C23 C21 C24 C25 159.00(13) . . . . ?
C22 C21 C24 C25 40.62(17) . . . . ?
C12 C21 C24 C25 -79.88(15) . . . . ?
C29 C24 C25 C26 1.0(2) . . . . ?
C21 C24 C25 C26 -176.05(13) . . . . ?
C24 C25 C26 C27 -1.6(2) . . . . ?
C25 C26 C27 C28 0.9(2) . . . . ?
C26 C27 C28 C29 0.3(2) . . . . ?
C25 C24 C29 C28 0.2(2) . . . . ?
C21 C24 C29 C28 177.28(14) . . . . ?
C27 C28 C29 C24 -0.9(2) . . . . ?

_refine_diff_density_max         0.150
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.037


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
