# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_d8v23394_0m
_database_code_depnum_ccdc_archive 'CCDC 2305869'
loop_
_audit_author_name
_audit_author_address
HP
;East China Normal University
China
;
_audit_update_record             
;
2023-11-06 deposited with the CCDC.	2024-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        2a
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35

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                   7.9979(3)
_cell_length_b                   14.3194(5)
_cell_length_c                   13.4938(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.7040(10)
_cell_angle_gamma                90
_cell_volume                     1544.70(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    5962
_cell_measurement_theta_min      5.690
_cell_measurement_theta_max      54.558

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6535
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(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            14655
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.918
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3028
_reflns_number_gt                2409
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0324P)²+0.3957P] 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
_refine_ls_extinction_coef       0.029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3028
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.0957
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.47490(14) 0.82383(8) 0.65719(8) 0.0476(3) Uani 1 1 d . . . . .
O2 O 0.21612(13) 0.92188(7) 0.53018(7) 0.0392(3) Uani 1 1 d . . . . .
N1 N 0.19647(14) 0.76964(8) 0.45782(8) 0.0318(3) Uani 1 1 d . . . . .
C1 C 0.22481(18) 0.82488(10) 0.54726(10) 0.0318(3) Uani 1 1 d . . . . .
C2 C 0.40138(18) 0.79166(10) 0.58433(10) 0.0328(3) Uani 1 1 d . . . . .
C3 C 0.45168(18) 0.71808(10) 0.51811(10) 0.0321(3) Uani 1 1 d . . . . .
C4 C 0.59262(19) 0.66149(12) 0.52024(11) 0.0418(4) Uani 1 1 d . . . . .
H4 H 0.6745 0.6674 0.5713 0.050 Uiso 1 1 calc R U . . .
C5 C 0.6101(2) 0.59652(12) 0.44620(12) 0.0481(4) Uani 1 1 d . . . . .
H5 H 0.7039 0.5569 0.4467 0.058 Uiso 1 1 calc R U . . .
C6 C 0.4883(2) 0.58965(11) 0.37042(12) 0.0443(4) Uani 1 1 d . . . . .
H6 H 0.5026 0.5452 0.3202 0.053 Uiso 1 1 calc R U . . .
C7 C 0.3477(2) 0.64559(11) 0.36629(11) 0.0381(4) Uani 1 1 d . . . . .
H7 H 0.2679 0.6404 0.3140 0.046 Uiso 1 1 calc R U . . .
C8 C 0.32815(17) 0.71022(9) 0.44264(10) 0.0297(3) Uani 1 1 d . . . . .
C9 C 0.07223(19) 0.79512(11) 0.38191(11) 0.0387(4) Uani 1 1 d . . . . .
H9A H -0.0252 0.8222 0.4136 0.046 Uiso 1 1 calc R U . . .
H9B H 0.0352 0.7387 0.3464 0.046 Uiso 1 1 calc R U . . .
C10 C 0.1395(2) 0.86475(12) 0.30803(11) 0.0442(4) Uani 1 1 d . . . . .
H10A H 0.0560 0.8737 0.2543 0.053 Uiso 1 1 calc R U . . .
H10B H 0.2403 0.8387 0.2790 0.053 Uiso 1 1 calc R U . . .
C11 C 0.1821(2) 0.95924(12) 0.35389(11) 0.0465(4) Uani 1 1 d . . . . .
H11A H 0.2329 0.9984 0.3034 0.056 Uiso 1 1 calc R U . . .
H11B H 0.0779 0.9896 0.3729 0.056 Uiso 1 1 calc R U . . .
C12 C 0.2996(2) 0.95525(11) 0.44396(11) 0.0430(4) Uani 1 1 d . . . . .
H12A H 0.3935 0.9138 0.4301 0.052 Uiso 1 1 calc R U . . .
H12B H 0.3447 1.0178 0.4574 0.052 Uiso 1 1 calc R U . . .
C13 C 0.09528(19) 0.80566(10) 0.62627(10) 0.0369(4) Uani 1 1 d . . . . .
H13A H 0.1186 0.8466 0.6832 0.044 Uiso 1 1 calc R U . . .
H13B H -0.0159 0.8218 0.5990 0.044 Uiso 1 1 calc R U . . .
C14 C 0.09260(17) 0.70601(10) 0.66174(10) 0.0342(4) Uani 1 1 d . . . . .
C15 C 0.1648(2) 0.68174(12) 0.75295(11) 0.0446(4) Uani 1 1 d . . . . .
H15 H 0.2142 0.7281 0.7935 0.053 Uiso 1 1 calc R U . . .
C16 C 0.1647(2) 0.58992(14) 0.78460(14) 0.0565(5) Uani 1 1 d . . . . .
H16 H 0.2156 0.5742 0.8460 0.068 Uiso 1 1 calc R U . . .
C17 C 0.0910(2) 0.52160(14) 0.72716(15) 0.0605(5) Uani 1 1 d . . . . .
H17 H 0.0909 0.4593 0.7492 0.073 Uiso 1 1 calc R U . . .
C18 C 0.0171(2) 0.54468(12) 0.63695(14) 0.0534(5) Uani 1 1 d . . . . .
H18 H -0.0345 0.4981 0.5976 0.064 Uiso 1 1 calc R U . . .
C19 C 0.01869(19) 0.63598(11) 0.60420(12) 0.0409(4) Uani 1 1 d . . . . .
H19 H -0.0309 0.6510 0.5422 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 C2 1.2207(16) . ?
O2 C1 1.4093(17) . ?
O2 C12 1.4399(18) . ?
N1 C8 1.3740(18) . ?
N1 C9 1.4524(17) . ?
N1 C1 1.4550(17) . ?
C1 C13 1.534(2) . ?
C1 C2 1.558(2) . ?
C2 C3 1.4463(19) . ?
C3 C4 1.388(2) . ?
C3 C8 1.4022(19) . ?
C4 C5 1.375(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.395(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.381(2) . ?
C6 H6 0.9400 . ?
C7 C8 1.3971(19) . ?
C7 H7 0.9400 . ?
C9 C10 1.520(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 C11 1.522(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 C12 1.515(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 C14 1.505(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 C15 1.388(2) . ?
C14 C19 1.389(2) . ?
C15 C16 1.382(2) . ?
C15 H15 0.9400 . ?
C16 C17 1.370(3) . ?
C16 H16 0.9400 . ?
C17 C18 1.377(3) . ?
C17 H17 0.9400 . ?
C18 C19 1.380(2) . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?

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
C1 O2 C12 115.94(11) . . ?
C8 N1 C9 124.18(11) . . ?
C8 N1 C1 111.05(11) . . ?
C9 N1 C1 122.34(11) . . ?
O2 C1 N1 113.23(11) . . ?
O2 C1 C13 105.04(11) . . ?
N1 C1 C13 112.79(12) . . ?
O2 C1 C2 113.15(12) . . ?
N1 C1 C2 102.57(11) . . ?
C13 C1 C2 110.27(11) . . ?
O1 C2 C3 129.52(14) . . ?
O1 C2 C1 123.61(13) . . ?
C3 C2 C1 106.86(11) . . ?
C4 C3 C8 121.50(13) . . ?
C4 C3 C2 130.79(14) . . ?
C8 C3 C2 107.71(12) . . ?
C5 C4 C3 118.70(15) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 119.75(15) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 122.63(15) . . ?
C7 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C6 C7 C8 117.60(14) . . ?
C6 C7 H7 121.2 . . ?
C8 C7 H7 121.2 . . ?
N1 C8 C7 128.54(13) . . ?
N1 C8 C3 111.63(12) . . ?
C7 C8 C3 119.80(13) . . ?
N1 C9 C10 112.29(13) . . ?
N1 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 C11 113.31(13) . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C10 114.73(13) . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
O2 C12 C11 111.68(13) . . ?
O2 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
O2 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C1 114.04(12) . . ?
C14 C13 H13A 108.7 . . ?
C1 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C1 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C19 118.27(15) . . ?
C15 C14 C13 120.65(14) . . ?
C19 C14 C13 121.08(13) . . ?
C16 C15 C14 120.52(17) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 120.57(17) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 119.63(17) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C19 120.17(18) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 120.83(16) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?

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
C12 O2 C1 N1 -43.67(16) . . . . ?
C12 O2 C1 C13 -167.16(12) . . . . ?
C12 O2 C1 C2 72.50(14) . . . . ?
C8 N1 C1 O2 123.92(13) . . . . ?
C9 N1 C1 O2 -39.01(18) . . . . ?
C8 N1 C1 C13 -116.96(13) . . . . ?
C9 N1 C1 C13 80.11(16) . . . . ?
C8 N1 C1 C2 1.64(14) . . . . ?
C9 N1 C1 C2 -161.29(12) . . . . ?
O2 C1 C2 O1 55.15(18) . . . . ?
N1 C1 C2 O1 177.49(13) . . . . ?
C13 C1 C2 O1 -62.16(18) . . . . ?
O2 C1 C2 C3 -125.92(12) . . . . ?
N1 C1 C2 C3 -3.59(14) . . . . ?
C13 C1 C2 C3 116.77(13) . . . . ?
O1 C2 C3 C4 2.6(3) . . . . ?
C1 C2 C3 C4 -176.22(15) . . . . ?
O1 C2 C3 C8 -176.88(15) . . . . ?
C1 C2 C3 C8 4.28(15) . . . . ?
C8 C3 C4 C5 0.0(2) . . . . ?
C2 C3 C4 C5 -179.41(15) . . . . ?
C3 C4 C5 C6 0.9(2) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C5 C6 C7 C8 -0.9(2) . . . . ?
C9 N1 C8 C7 -18.2(2) . . . . ?
C1 N1 C8 C7 179.24(14) . . . . ?
C9 N1 C8 C3 163.55(13) . . . . ?
C1 N1 C8 C3 1.00(16) . . . . ?
C6 C7 C8 N1 -176.33(14) . . . . ?
C6 C7 C8 C3 1.8(2) . . . . ?
C4 C3 C8 N1 177.03(13) . . . . ?
C2 C3 C8 N1 -3.42(16) . . . . ?
C4 C3 C8 C7 -1.4(2) . . . . ?
C2 C3 C8 C7 178.17(13) . . . . ?
C8 N1 C9 C10 -75.43(18) . . . . ?
C1 N1 C9 C10 85.24(16) . . . . ?
N1 C9 C10 C11 -65.42(17) . . . . ?
C9 C10 C11 C12 53.75(19) . . . . ?
C1 O2 C12 C11 92.28(16) . . . . ?
C10 C11 C12 O2 -74.59(17) . . . . ?
O2 C1 C13 C14 -175.59(12) . . . . ?
N1 C1 C13 C14 60.64(16) . . . . ?
C2 C1 C13 C14 -53.36(16) . . . . ?
C1 C13 C14 C15 103.38(16) . . . . ?
C1 C13 C14 C19 -76.37(18) . . . . ?
C19 C14 C15 C16 0.9(2) . . . . ?
C13 C14 C15 C16 -178.90(14) . . . . ?
C14 C15 C16 C17 -1.0(3) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C16 C17 C18 C19 0.6(3) . . . . ?
C17 C18 C19 C14 -0.7(2) . . . . ?
C15 C14 C19 C18 0.0(2) . . . . ?
C13 C14 C19 C18 179.77(14) . . . . ?

_refine_diff_density_max         0.151
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.031

_shelxl_version_number           2013-4



