# 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_240117_zyl1_0m
_database_code_depnum_ccdc_archive 'CCDC 2325997'
loop_
_audit_author_name
_audit_author_address
Yulei
;Qufu Normal University
China
;
_audit_update_record             
;
2024-01-17 deposited with the CCDC.	2024-03-22 downloaded from the CCDC.
;
_audit_creation_date             2024-01-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 N2 O2'
_chemical_formula_sum            'C15 H14 N2 O2'
_chemical_formula_weight         254.28
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.000(2)
_cell_length_b                   9.0818(13)
_cell_length_c                   19.698(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2683.5(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1909
_cell_measurement_temperature    273
_cell_measurement_theta_max      19.729
_cell_measurement_theta_min      2.474
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1042 before and 0.0691 after correction.
The Ratio of minimum to maximum transmission is 0.8642.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1411
_diffrn_reflns_av_unetI/netI     0.0865
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20275
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         26.390
_diffrn_reflns_theta_min         2.068
_diffrn_ambient_temperature      273
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  apex
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1175
_reflns_number_total             2749
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2749
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1849
_refine_ls_R_factor_gt           0.0677
_refine_ls_restrained_S_all      1.006
_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)+(0.0821P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1411
_refine_ls_wR_factor_ref         0.1911
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C11(H11), C15(H15), C5(H5), C9(H9), C7(H7), C14(H14), C8(H8),
 C12(H12), C13(H13), C6(H6)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
O2 O 0.46896(16) 0.4939(2) 0.38437(11) 0.0603(7) Uani 1 1 d . . . . .
N1 N 0.30250(19) 0.4517(3) 0.50480(13) 0.0511(7) Uani 1 1 d . . . . .
N2 N 0.24392(19) 0.3547(3) 0.53002(13) 0.0557(8) Uani 1 1 d . . . . .
H2 H 0.236886 0.269984 0.511284 0.067 Uiso 1 1 calc R U . . .
O1 O 0.4093(2) 0.6602(3) 0.45373(13) 0.0936(10) Uani 1 1 d . . . . .
C3 C 0.3514(2) 0.4156(3) 0.45336(16) 0.0478(8) Uani 1 1 d . . . . .
C4 C 0.3540(2) 0.2687(3) 0.42027(16) 0.0478(8) Uani 1 1 d . . . . .
C10 C 0.1946(2) 0.3938(4) 0.58720(16) 0.0481(8) Uani 1 1 d . . . . .
C2 C 0.4115(3) 0.5363(4) 0.43173(17) 0.0566(9) Uani 1 1 d . . . . .
C11 C 0.2162(2) 0.5178(4) 0.62480(17) 0.0594(10) Uani 1 1 d . . . . .
H11 H 0.263431 0.577557 0.611514 0.071 Uiso 1 1 calc R U . . .
C15 C 0.1239(2) 0.3072(4) 0.60754(18) 0.0590(9) Uani 1 1 d . . . . .
H15 H 0.107974 0.224884 0.582190 0.071 Uiso 1 1 calc R U . . .
C5 C 0.3233(2) 0.2484(4) 0.35529(18) 0.0631(10) Uani 1 1 d . . . . .
H5 H 0.299892 0.327725 0.331363 0.076 Uiso 1 1 calc R U . . .
C9 C 0.3903(2) 0.1504(4) 0.45462(18) 0.0651(11) Uani 1 1 d . . . . .
H9 H 0.411234 0.162912 0.498698 0.078 Uiso 1 1 calc R U . . .
C7 C 0.3644(3) -0.0052(4) 0.3602(3) 0.0779(13) Uani 1 1 d . . . . .
H7 H 0.368066 -0.097479 0.339952 0.094 Uiso 1 1 calc R U . . .
C14 C 0.0769(3) 0.3424(5) 0.6652(2) 0.0758(12) Uani 1 1 d . . . . .
H14 H 0.030327 0.282074 0.679209 0.091 Uiso 1 1 calc R U . . .
C8 C 0.3960(3) 0.0142(4) 0.4242(3) 0.0763(12) Uani 1 1 d . . . . .
H8 H 0.421334 -0.064420 0.447496 0.092 Uiso 1 1 calc R U . . .
C12 C 0.1677(3) 0.5520(4) 0.68163(18) 0.0719(11) Uani 1 1 d . . . . .
H12 H 0.182509 0.635592 0.706498 0.086 Uiso 1 1 calc R U . . .
C1 C 0.5322(2) 0.6038(4) 0.3622(2) 0.0769(12) Uani 1 1 d . . . . .
H1A H 0.569230 0.563399 0.327142 0.115 Uiso 1 1 calc R U . . .
H1B H 0.568619 0.633305 0.399906 0.115 Uiso 1 1 calc R U . . .
H1C H 0.500653 0.687819 0.344922 0.115 Uiso 1 1 calc R U . . .
C13 C 0.0981(3) 0.4661(5) 0.7026(2) 0.0807(12) Uani 1 1 d . . . . .
H13 H 0.065654 0.490500 0.741235 0.097 Uiso 1 1 calc R U . . .
C6 C 0.3269(3) 0.1104(5) 0.3249(2) 0.0779(12) Uani 1 1 d . . . . .
H6 H 0.304316 0.096215 0.281368 0.094 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
O2 C2 1.327(4) . ?
O2 C1 1.444(4) . ?
N1 N2 1.340(3) . ?
N1 C3 1.293(4) . ?
N2 H2 0.8600 . ?
N2 C10 1.393(4) . ?
O1 C2 1.206(4) . ?
C3 C4 1.485(4) . ?
C3 C2 1.482(5) . ?
C4 C5 1.373(4) . ?
C4 C9 1.382(4) . ?
C10 C11 1.386(4) . ?
C10 C15 1.381(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.371(5) . ?
C15 H15 0.9300 . ?
C15 C14 1.374(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.377(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.359(5) . ?
C7 C6 1.379(5) . ?
C14 H14 0.9300 . ?
C14 C13 1.381(5) . ?
C8 H8 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.368(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C13 H13 0.9300 . ?
C6 H6 0.9300 . ?

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
C2 O2 C1 116.0(3) . . ?
C3 N1 N2 119.7(3) . . ?
N1 N2 H2 120.7 . . ?
N1 N2 C10 118.7(3) . . ?
C10 N2 H2 120.7 . . ?
N1 C3 C4 125.9(3) . . ?
N1 C3 C2 112.5(3) . . ?
C2 C3 C4 121.5(3) . . ?
C5 C4 C3 121.4(3) . . ?
C5 C4 C9 118.9(3) . . ?
C9 C4 C3 119.6(3) . . ?
C11 C10 N2 121.0(3) . . ?
C15 C10 N2 119.8(3) . . ?
C15 C10 C11 119.2(3) . . ?
O2 C2 C3 112.5(3) . . ?
O1 C2 O2 122.7(3) . . ?
O1 C2 C3 124.8(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C15 H15 120.0 . . ?
C14 C15 C10 120.1(3) . . ?
C14 C15 H15 120.0 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.7(4) . . ?
C6 C5 H5 119.6 . . ?
C4 C9 H9 119.7 . . ?
C8 C9 C4 120.7(4) . . ?
C8 C9 H9 119.7 . . ?
C8 C7 H7 119.6 . . ?
C8 C7 C6 120.8(4) . . ?
C6 C7 H7 119.6 . . ?
C15 C14 H14 119.6 . . ?
C15 C14 C13 120.8(4) . . ?
C13 C14 H14 119.6 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 C9 119.9(4) . . ?
C7 C8 H8 120.0 . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.5(4) . . ?
C13 C12 H12 119.3 . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C14 C13 H13 120.7 . . ?
C12 C13 C14 118.6(4) . . ?
C12 C13 H13 120.7 . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 118.9(4) . . ?
C7 C6 H6 120.5 . . ?

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 N2 C10 C11 -11.6(4) . . . . ?
N1 N2 C10 C15 169.3(3) . . . . ?
N1 C3 C4 C5 112.9(4) . . . . ?
N1 C3 C4 C9 -69.0(5) . . . . ?
N1 C3 C2 O2 172.5(3) . . . . ?
N1 C3 C2 O1 -7.9(5) . . . . ?
N2 N1 C3 C4 -4.2(5) . . . . ?
N2 N1 C3 C2 179.4(3) . . . . ?
N2 C10 C11 C12 -178.7(3) . . . . ?
N2 C10 C15 C14 177.8(3) . . . . ?
C3 N1 N2 C10 177.3(3) . . . . ?
C3 C4 C5 C6 179.5(3) . . . . ?
C3 C4 C9 C8 -178.0(3) . . . . ?
C4 C3 C2 O2 -4.1(5) . . . . ?
C4 C3 C2 O1 175.5(3) . . . . ?
C4 C5 C6 C7 -2.0(5) . . . . ?
C4 C9 C8 C7 -1.0(5) . . . . ?
C10 C11 C12 C13 0.2(6) . . . . ?
C10 C15 C14 C13 1.6(5) . . . . ?
C2 C3 C4 C5 -71.0(4) . . . . ?
C2 C3 C4 C9 107.1(4) . . . . ?
C11 C10 C15 C14 -1.4(5) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
C15 C10 C11 C12 0.5(5) . . . . ?
C15 C14 C13 C12 -1.0(6) . . . . ?
C5 C4 C9 C8 0.1(5) . . . . ?
C9 C4 C5 C6 1.4(5) . . . . ?
C8 C7 C6 C5 1.2(6) . . . . ?
C1 O2 C2 O1 2.5(5) . . . . ?
C1 O2 C2 C3 -177.8(3) . . . . ?
C6 C7 C8 C9 0.3(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
