# 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 
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data_mo_230411_xy_0
_database_code_depnum_ccdc_archive 'CCDC 2306450'
loop_
_audit_author_name
_audit_author_address
'Xufeng Lin'
;Zhejiang University
China
;
_audit_update_record             
;
2023-11-08 deposited with the CCDC.	2024-05-01 downloaded from the CCDC.
;
_audit_creation_date             2023-04-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 N2 O2'
_chemical_formula_sum            'C19 H18 N2 O2'
_chemical_formula_weight         306.35
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   13.0152(3)
_cell_length_b                   9.9594(3)
_cell_length_c                   11.9574(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.5640(10)
_cell_angle_gamma                90
_cell_volume                     1548.41(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8405
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0825 before and 0.0575 after correction.
The Ratio of minimum to maximum transmission is 0.9242.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23366
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_min         2.576
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2791
_reflns_number_total             3555
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3555
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0556P)²+0.5392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1212
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.58427(8) 0.54937(11) 0.22946(9) 0.0363(3) Uani 1 1 d . . . . .
O2 O 0.73301(9) 0.64774(12) 0.57404(9) 0.0405(3) Uani 1 1 d . . . . .
N1 N 0.66804(9) 0.63036(12) 0.39048(10) 0.0281(3) Uani 1 1 d . . . . .
N2 N 0.88344(9) 0.63974(13) 0.39323(11) 0.0342(3) Uani 1 1 d . . . . .
H2 H 0.916658 0.649315 0.458470 0.041 Uiso 1 1 calc R U . . .
C1 C 0.54862(11) 0.29819(15) 0.37965(12) 0.0315(3) Uani 1 1 d . . . . .
H1 H 0.516103 0.279615 0.308627 0.038 Uiso 1 1 calc R U . . .
C2 C 0.55023(12) 0.20410(15) 0.46557(13) 0.0357(3) Uani 1 1 d . . . . .
H2A H 0.518886 0.118979 0.452878 0.043 Uiso 1 1 calc R U . . .
C3 C 0.59675(13) 0.23231(16) 0.56940(13) 0.0389(4) Uani 1 1 d . . . . .
H3 H 0.597435 0.165850 0.626419 0.047 Uiso 1 1 calc R U . . .
C4 C 0.64254(12) 0.35649(16) 0.59162(13) 0.0368(4) Uani 1 1 d . . . . .
H4 H 0.673109 0.376775 0.663265 0.044 Uiso 1 1 calc R U . . .
C5 C 0.64181(10) 0.44871(14) 0.50574(11) 0.0283(3) Uani 1 1 d . . . . .
C6 C 0.59612(10) 0.41943(14) 0.40178(11) 0.0261(3) Uani 1 1 d . . . . .
C7 C 0.61207(10) 0.53561(14) 0.32665(12) 0.0277(3) Uani 1 1 d . . . . .
C8 C 0.68722(11) 0.58596(15) 0.50017(12) 0.0301(3) Uani 1 1 d . . . . .
C9 C 0.71009(11) 0.75129(14) 0.34029(12) 0.0302(3) Uani 1 1 d . . . . .
H9 H 0.685932 0.753346 0.259740 0.036 Uiso 1 1 calc R U . . .
C10 C 0.67631(12) 0.88276(15) 0.39433(15) 0.0389(4) Uani 1 1 d . . . . .
H10A H 0.613994 0.919404 0.354808 0.047 Uiso 1 1 calc R U . . .
H10B H 0.661941 0.868980 0.474126 0.047 Uiso 1 1 calc R U . . .
C11 C 0.76796(12) 0.97617(16) 0.38231(16) 0.0417(4) Uani 1 1 d . . . . .
H11A H 0.769498 1.012949 0.305487 0.050 Uiso 1 1 calc R U . . .
H11B H 0.766446 1.051378 0.436357 0.050 Uiso 1 1 calc R U . . .
C12 C 0.85943(12) 0.88428(16) 0.40799(16) 0.0424(4) Uani 1 1 d . . . . .
H12A H 0.868374 0.867338 0.489422 0.051 Uiso 1 1 calc R U . . .
H12B H 0.923525 0.923910 0.380993 0.051 Uiso 1 1 calc R U . . .
C13 C 0.83197(11) 0.75534(15) 0.34500(13) 0.0319(3) Uani 1 1 d . . . . .
H13 H 0.854595 0.765540 0.266622 0.038 Uiso 1 1 calc R U . . .
C14 C 0.88384(10) 0.51421(15) 0.34307(13) 0.0319(3) Uani 1 1 d . . . . .
C15 C 0.85712(13) 0.49409(18) 0.22984(14) 0.0405(4) Uani 1 1 d . . . . .
H15 H 0.833282 0.567294 0.184832 0.049 Uiso 1 1 calc R U . . .
C16 C 0.86540(14) 0.36711(19) 0.18306(15) 0.0475(4) Uani 1 1 d . . . . .
H16 H 0.847548 0.354733 0.105840 0.057 Uiso 1 1 calc R U . . .
C17 C 0.89901(13) 0.25856(18) 0.24642(17) 0.0480(4) Uani 1 1 d . . . . .
H17 H 0.905770 0.172510 0.213258 0.058 Uiso 1 1 calc R U . . .
C18 C 0.92254(13) 0.27762(17) 0.35876(17) 0.0458(4) Uani 1 1 d . . . . .
H18 H 0.944894 0.203501 0.403548 0.055 Uiso 1 1 calc R U . . .
C19 C 0.91420(12) 0.40225(16) 0.40715(14) 0.0386(4) Uani 1 1 d . . . . .
H19 H 0.929267 0.412466 0.485159 0.046 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 C7 1.2093(17) . ?
O2 C8 1.2111(17) . ?
N1 C7 1.3978(17) . ?
N1 C8 1.3961(18) . ?
N1 C9 1.4627(18) . ?
N2 H2 0.8800 . ?
N2 C13 1.4395(18) . ?
N2 C14 1.387(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.390(2) . ?
C1 C6 1.377(2) . ?
C2 H2A 0.9500 . ?
C2 C3 1.386(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(2) . ?
C5 C6 1.3849(19) . ?
C5 C8 1.492(2) . ?
C6 C7 1.4852(19) . ?
C9 H9 1.0000 . ?
C9 C10 1.533(2) . ?
C9 C13 1.585(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.525(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.522(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.523(2) . ?
C13 H13 1.0000 . ?
C14 C15 1.397(2) . ?
C14 C19 1.400(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.380(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.377(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.376(2) . ?
C19 H19 0.9500 . ?

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
C7 N1 C9 121.82(11) . . ?
C8 N1 C7 111.47(12) . . ?
C8 N1 C9 126.29(12) . . ?
C13 N2 H2 118.0 . . ?
C14 N2 H2 118.0 . . ?
C14 N2 C13 123.95(12) . . ?
C2 C1 H1 121.4 . . ?
C6 C1 H1 121.4 . . ?
C6 C1 C2 117.23(13) . . ?
C1 C2 H2A 119.4 . . ?
C3 C2 C1 121.13(14) . . ?
C3 C2 H2A 119.4 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.13(14) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 121.3 . . ?
C5 C4 C3 117.46(14) . . ?
C5 C4 H4 121.3 . . ?
C4 C5 C6 121.14(13) . . ?
C4 C5 C8 130.90(13) . . ?
C6 C5 C8 107.93(12) . . ?
C1 C6 C5 121.89(13) . . ?
C1 C6 C7 129.85(13) . . ?
C5 C6 C7 108.23(12) . . ?
O1 C7 N1 125.06(13) . . ?
O1 C7 C6 128.73(13) . . ?
N1 C7 C6 106.22(11) . . ?
O2 C8 N1 125.85(14) . . ?
O2 C8 C5 128.02(14) . . ?
N1 C8 C5 106.12(11) . . ?
N1 C9 H9 107.7 . . ?
N1 C9 C10 114.25(12) . . ?
N1 C9 C13 113.49(11) . . ?
C10 C9 H9 107.7 . . ?
C10 C9 C13 105.58(11) . . ?
C13 C9 H9 107.7 . . ?
C9 C10 H10A 111.0 . . ?
C9 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
C11 C10 C9 103.95(13) . . ?
C11 C10 H10A 111.0 . . ?
C11 C10 H10B 111.0 . . ?
C10 C11 H11A 111.2 . . ?
C10 C11 H11B 111.2 . . ?
H11A C11 H11B 109.1 . . ?
C12 C11 C10 102.84(13) . . ?
C12 C11 H11A 111.2 . . ?
C12 C11 H11B 111.2 . . ?
C11 C12 H12A 110.9 . . ?
C11 C12 H12B 110.9 . . ?
C11 C12 C13 104.08(12) . . ?
H12A C12 H12B 109.0 . . ?
C13 C12 H12A 110.9 . . ?
C13 C12 H12B 110.9 . . ?
N2 C13 C9 116.16(12) . . ?
N2 C13 C12 112.43(12) . . ?
N2 C13 H13 107.8 . . ?
C9 C13 H13 107.8 . . ?
C12 C13 C9 104.55(12) . . ?
C12 C13 H13 107.8 . . ?
N2 C14 C15 122.87(14) . . ?
N2 C14 C19 119.20(14) . . ?
C15 C14 C19 117.91(15) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.03(16) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.37(17) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 120.7 . . ?
C18 C17 C16 118.59(16) . . ?
C18 C17 H17 120.7 . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.08(16) . . ?
C19 C18 H18 119.5 . . ?
C14 C19 H19 119.5 . . ?
C18 C19 C14 120.94(16) . . ?
C18 C19 H19 119.5 . . ?

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
N1 C9 C10 C11 148.05(13) . . . . ?
N1 C9 C13 N2 2.16(18) . . . . ?
N1 C9 C13 C12 -122.35(13) . . . . ?
N2 C14 C15 C16 175.88(15) . . . . ?
N2 C14 C19 C18 -175.41(14) . . . . ?
C1 C2 C3 C4 0.7(2) . . . . ?
C1 C6 C7 O1 1.8(2) . . . . ?
C1 C6 C7 N1 -177.75(14) . . . . ?
C2 C1 C6 C5 -1.4(2) . . . . ?
C2 C1 C6 C7 176.35(13) . . . . ?
C2 C3 C4 C5 -1.4(2) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C3 C4 C5 C8 -177.05(15) . . . . ?
C4 C5 C6 C1 0.7(2) . . . . ?
C4 C5 C6 C7 -177.53(13) . . . . ?
C4 C5 C8 O2 -2.5(3) . . . . ?
C4 C5 C8 N1 176.56(15) . . . . ?
C5 C6 C7 O1 179.83(14) . . . . ?
C5 C6 C7 N1 0.26(15) . . . . ?
C6 C1 C2 C3 0.7(2) . . . . ?
C6 C5 C8 O2 179.45(15) . . . . ?
C6 C5 C8 N1 -1.49(15) . . . . ?
C7 N1 C8 O2 -179.22(14) . . . . ?
C7 N1 C8 C5 1.71(15) . . . . ?
C7 N1 C9 C10 124.41(14) . . . . ?
C7 N1 C9 C13 -114.45(14) . . . . ?
C8 N1 C7 O1 179.15(13) . . . . ?
C8 N1 C7 C6 -1.26(15) . . . . ?
C8 N1 C9 C10 -63.68(18) . . . . ?
C8 N1 C9 C13 57.45(18) . . . . ?
C8 C5 C6 C1 178.96(13) . . . . ?
C8 C5 C6 C7 0.75(15) . . . . ?
C9 N1 C7 O1 -7.9(2) . . . . ?
C9 N1 C7 C6 171.73(11) . . . . ?
C9 N1 C8 O2 8.2(2) . . . . ?
C9 N1 C8 C5 -170.91(12) . . . . ?
C9 C10 C11 C12 -40.59(17) . . . . ?
C10 C9 C13 N2 128.05(14) . . . . ?
C10 C9 C13 C12 3.53(15) . . . . ?
C10 C11 C12 C13 43.22(17) . . . . ?
C11 C12 C13 N2 -155.33(13) . . . . ?
C11 C12 C13 C9 -28.47(16) . . . . ?
C13 N2 C14 C15 16.5(2) . . . . ?
C13 N2 C14 C19 -164.81(14) . . . . ?
C13 C9 C10 C11 22.63(16) . . . . ?
C14 N2 C13 C9 69.45(18) . . . . ?
C14 N2 C13 C12 -170.19(13) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C15 C14 C19 C18 3.3(2) . . . . ?
C15 C16 C17 C18 1.3(3) . . . . ?
C16 C17 C18 C19 -0.8(3) . . . . ?
C17 C18 C19 C14 -1.5(2) . . . . ?
C19 C14 C15 C16 -2.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
