# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_250708d_a
_audit_block_doi                 10.5517/ccdc.csd.cc2qxghm
_database_code_depnum_ccdc_archive 'CCDC 2529801'
loop_
_audit_author_name
_audit_author_address
'CCDC Fx'
;Fudan university
China
;
_audit_update_record             
;
2026-02-09 deposited with the CCDC.	2026-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N O2'
_chemical_formula_weight         291.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   27.2942(12)
_cell_length_b                   5.7884(3)
_cell_length_c                   9.2458(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.244(2)
_cell_angle_gamma                90
_cell_volume                     1449.08(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9879
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      60.49

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.440
_exptl_absorpt_coefficient_mu    0.439
_shelx_estimated_absorpt_T_min   0.720
_shelx_estimated_absorpt_T_max   0.830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.509
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\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            14119
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.262
_diffrn_reflns_theta_max         56.487
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2884
_reflns_number_gt                2550
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (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)+(0.0943P)²+0.4442P] 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     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2884
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1605
_refine_ls_wR_factor_gt          0.1550
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_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 0.77955(4) 0.5993(2) 0.32770(11) 0.0330(3) Uani 1 1 d . . . . .
O2 O 0.95509(4) 0.5329(2) 0.84124(12) 0.0360(3) Uani 1 1 d . . . . .
N1 N 0.59975(5) 0.2999(3) 0.05847(15) 0.0351(4) Uani 1 1 d . . . . .
C1 C 0.52927(7) 0.3070(4) -0.1269(2) 0.0473(5) Uani 1 1 d . . . . .
H1A H 0.522542 0.163058 -0.077276 0.071 Uiso 1 1 calc R U . . .
H1B H 0.534961 0.272838 -0.227291 0.071 Uiso 1 1 calc R U . . .
H1C H 0.500908 0.411118 -0.128076 0.071 Uiso 1 1 calc R U . . .
C2 C 0.57449(6) 0.4210(3) -0.04727(19) 0.0367(4) Uani 1 1 d . . . . .
C3 C 0.58926(6) 0.6428(3) -0.08862(19) 0.0388(4) Uani 1 1 d . . . . .
H3 H 0.569531 0.725503 -0.163308 0.047 Uiso 1 1 calc R U . . .
C4 C 0.63183(6) 0.7381(3) -0.02137(19) 0.0361(4) Uani 1 1 d . . . . .
H4 H 0.641752 0.887924 -0.047916 0.043 Uiso 1 1 calc R U . . .
C5 C 0.66108(6) 0.6112(3) 0.08846(17) 0.0298(4) Uani 1 1 d . . . . .
C6 C 0.64305(6) 0.3922(3) 0.12631(16) 0.0296(4) Uani 1 1 d . . . . .
C7 C 0.70759(6) 0.6920(3) 0.15620(17) 0.0303(4) Uani 1 1 d . . . . .
H7 H 0.720209 0.838262 0.132553 0.036 Uiso 1 1 calc R U . . .
C8 C 0.73333(6) 0.5506(3) 0.25653(16) 0.0277(4) Uani 1 1 d . . . . .
C9 C 0.71574(6) 0.3350(3) 0.29786(16) 0.0285(4) Uani 1 1 d . . . . .
C10 C 0.67090(6) 0.2557(3) 0.23489(17) 0.0311(4) Uani 1 1 d . . . . .
H10 H 0.658545 0.111457 0.263318 0.037 Uiso 1 1 calc R U . . .
C11 C 0.79987(6) 0.3792(3) 0.38427(16) 0.0304(4) Uani 1 1 d . . . . .
H11 H 0.816033 0.302207 0.305809 0.037 Uiso 1 1 calc R U . . .
C12 C 0.75453(6) 0.2344(3) 0.41116(16) 0.0320(4) Uani 1 1 d . . . . .
H12A H 0.759794 0.067843 0.394173 0.038 Uiso 1 1 calc R U . . .
H12B H 0.745935 0.256899 0.511067 0.038 Uiso 1 1 calc R U . . .
C13 C 0.83874(6) 0.4237(3) 0.51142(15) 0.0292(4) Uani 1 1 d . . . . .
C14 C 0.83912(6) 0.6212(3) 0.59674(17) 0.0324(4) Uani 1 1 d . . . . .
H14 H 0.813038 0.729997 0.577885 0.039 Uiso 1 1 calc R U . . .
C15 C 0.87695(6) 0.6631(3) 0.70934(17) 0.0319(4) Uani 1 1 d . . . . .
H15 H 0.876600 0.799087 0.766749 0.038 Uiso 1 1 calc R U . . .
C16 C 0.91514(6) 0.5051(3) 0.73711(15) 0.0292(4) Uani 1 1 d . . . . .
C17 C 0.91437(6) 0.3020(3) 0.65550(17) 0.0333(4) Uani 1 1 d . . . . .
H17 H 0.939816 0.190579 0.676645 0.040 Uiso 1 1 calc R U . . .
C18 C 0.87666(6) 0.2630(3) 0.54410(17) 0.0323(4) Uani 1 1 d . . . . .
H18 H 0.876507 0.124652 0.488772 0.039 Uiso 1 1 calc R U . . .
C19 C 0.95840(7) 0.7440(3) 0.92130(19) 0.0399(4) Uani 1 1 d . . . . .
H19A H 0.961503 0.873376 0.854673 0.060 Uiso 1 1 calc R U . . .
H19B H 0.987404 0.739585 0.995425 0.060 Uiso 1 1 calc R U . . .
H19C H 0.928556 0.764224 0.968824 0.060 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 C8 1.3765(18) . ?
O1 C11 1.460(2) . ?
O2 C16 1.3700(19) . ?
O2 C19 1.425(2) . ?
N1 C2 1.324(2) . ?
N1 C6 1.374(2) . ?
C1 C2 1.507(2) . ?
C2 C3 1.413(3) . ?
C3 C4 1.363(2) . ?
C4 C5 1.415(2) . ?
C5 C6 1.420(2) . ?
C5 C7 1.422(2) . ?
C6 C10 1.420(2) . ?
C7 C8 1.363(2) . ?
C8 C9 1.407(2) . ?
C9 C10 1.367(2) . ?
C9 C12 1.509(2) . ?
C11 C13 1.503(2) . ?
C11 C12 1.541(2) . ?
C13 C14 1.389(2) . ?
C13 C18 1.396(2) . ?
C14 C15 1.392(2) . ?
C15 C16 1.386(2) . ?
C16 C17 1.395(2) . ?
C17 C18 1.380(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
C8 O1 C11 106.04(12) . . ?
C16 O2 C19 117.29(13) . . ?
C2 N1 C6 117.99(15) . . ?
N1 C2 C3 122.76(16) . . ?
N1 C2 C1 116.59(17) . . ?
C3 C2 C1 120.62(17) . . ?
C4 C3 C2 120.01(16) . . ?
C3 C4 C5 119.22(17) . . ?
C4 C5 C6 117.30(15) . . ?
C4 C5 C7 122.47(16) . . ?
C6 C5 C7 120.19(15) . . ?
N1 C6 C5 122.64(15) . . ?
N1 C6 C10 117.35(15) . . ?
C5 C6 C10 119.97(15) . . ?
C8 C7 C5 117.20(15) . . ?
C7 C8 O1 124.38(15) . . ?
C7 C8 C9 123.56(15) . . ?
O1 C8 C9 112.05(13) . . ?
C10 C9 C8 119.99(15) . . ?
C10 C9 C12 132.72(15) . . ?
C8 C9 C12 107.28(13) . . ?
C9 C10 C6 119.03(15) . . ?
O1 C11 C13 109.24(13) . . ?
O1 C11 C12 104.83(12) . . ?
C13 C11 C12 117.97(13) . . ?
C9 C12 C11 100.70(12) . . ?
C14 C13 C18 118.26(15) . . ?
C14 C13 C11 122.64(15) . . ?
C18 C13 C11 119.09(15) . . ?
C13 C14 C15 121.34(15) . . ?
C16 C15 C14 119.54(15) . . ?
O2 C16 C15 124.44(15) . . ?
O2 C16 C17 115.83(14) . . ?
C15 C16 C17 119.73(15) . . ?
C18 C17 C16 120.04(15) . . ?
C17 C18 C13 121.03(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
C6 N1 C2 C3 -2.5(2) . . . . ?
C6 N1 C2 C1 175.50(14) . . . . ?
N1 C2 C3 C4 1.8(3) . . . . ?
C1 C2 C3 C4 -176.12(16) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 -2.3(2) . . . . ?
C3 C4 C5 C7 175.46(15) . . . . ?
C2 N1 C6 C5 0.7(2) . . . . ?
C2 N1 C6 C10 -177.16(14) . . . . ?
C4 C5 C6 N1 1.6(2) . . . . ?
C7 C5 C6 N1 -176.19(14) . . . . ?
C4 C5 C6 C10 179.49(14) . . . . ?
C7 C5 C6 C10 1.7(2) . . . . ?
C4 C5 C7 C8 -177.48(15) . . . . ?
C6 C5 C7 C8 0.2(2) . . . . ?
C5 C7 C8 O1 177.51(13) . . . . ?
C5 C7 C8 C9 -1.6(2) . . . . ?
C11 O1 C8 C7 -161.30(15) . . . . ?
C11 O1 C8 C9 17.87(16) . . . . ?
C7 C8 C9 C10 1.0(2) . . . . ?
O1 C8 C9 C10 -178.21(13) . . . . ?
C7 C8 C9 C12 -179.52(15) . . . . ?
O1 C8 C9 C12 1.30(17) . . . . ?
C8 C9 C10 C6 1.0(2) . . . . ?
C12 C9 C10 C6 -178.36(15) . . . . ?
N1 C6 C10 C9 175.69(14) . . . . ?
C5 C6 C10 C9 -2.3(2) . . . . ?
C8 O1 C11 C13 -156.46(12) . . . . ?
C8 O1 C11 C12 -29.13(14) . . . . ?
C10 C9 C12 C11 160.96(17) . . . . ?
C8 C9 C12 C11 -18.46(16) . . . . ?
O1 C11 C12 C9 28.54(14) . . . . ?
C13 C11 C12 C9 150.31(14) . . . . ?
O1 C11 C13 C14 25.5(2) . . . . ?
C12 C11 C13 C14 -94.01(19) . . . . ?
O1 C11 C13 C18 -153.22(14) . . . . ?
C12 C11 C13 C18 87.28(19) . . . . ?
C18 C13 C14 C15 1.9(2) . . . . ?
C11 C13 C14 C15 -176.78(14) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C19 O2 C16 C15 -3.0(2) . . . . ?
C19 O2 C16 C17 176.73(14) . . . . ?
C14 C15 C16 O2 177.43(14) . . . . ?
C14 C15 C16 C17 -2.3(2) . . . . ?
O2 C16 C17 C18 -177.34(14) . . . . ?
C15 C16 C17 C18 2.4(2) . . . . ?
C16 C17 C18 C13 -0.3(2) . . . . ?
C14 C13 C18 C17 -1.8(2) . . . . ?
C11 C13 C18 C17 176.93(14) . . . . ?

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.058

