# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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. 
# 
#######################################################################

data_11-0902
_database_code_depnum_ccdc_archive 'CCDC 2292549'
loop_
_audit_author_name
_audit_author_address
'Bin Wang'
;Anhui University of Chinese Medicine
China
;
_audit_update_record             
;
2023-09-03 deposited with the CCDC.	2024-10-17 downloaded from the CCDC.
;
_audit_creation_date             2023-02-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H12 N2 O2'
_chemical_formula_sum            'C17 H12 N2 O2'
_chemical_formula_weight         276.29
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20O2N2
_chemical_oxdiff_usercomment     \
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'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.65731(16)
_cell_length_b                   5.62441(16)
_cell_length_c                   20.6396(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.064(2)
_cell_angle_gamma                90
_cell_volume                     655.79(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2225
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.6570
_cell_measurement_theta_min      6.4650
_shelx_estimated_absorpt_T_max   0.857
_shelx_estimated_absorpt_T_min   0.833
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0102
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            2675
_diffrn_reflns_point_group_measured_fraction_full 0.751
_diffrn_reflns_point_group_measured_fraction_max 0.723
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.824
_diffrn_reflns_theta_min         4.290
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00 -14.00   1.00    3.00    --  -40.26  38.00  30.00   50
  2  ω    -10.00  26.00   1.00    3.00    --  -40.26  38.00  30.00   36
  3  ω   -115.00 -20.00   1.00    3.00    --  -40.26 -38.00  30.00   95
  4  ω    125.00 176.00   1.00    6.00    --  106.05  77.00-180.00   51
  5  ω     46.00 103.00   1.00    6.00    --  106.05-125.00  60.00   57
  6  ω     82.00 171.00   1.00    6.00    --  106.05  30.00   0.00   89
  7  ω     37.00 132.00   1.00    6.00    --  106.05 -45.00-180.00   95
  8  ω     56.00  83.00   1.00    6.00    --  106.05-125.00 120.00   27
  9  ω     30.00  99.00   1.00    6.00    --  106.05 -30.00  30.00   69
 10  ω    -64.00 -22.00   1.00    3.00    --  -42.01 125.00-180.00   42
 11  ω    -84.00 -16.00   1.00    3.00    --  -42.01 -57.00   0.00   68
 12  ω    -80.00 -38.00   1.00    3.00    --  -42.01 -38.00  90.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0608646000
_diffrn_orient_matrix_UB_12      0.0259902000
_diffrn_orient_matrix_UB_13      0.0732934000
_diffrn_orient_matrix_UB_21      0.2484768000
_diffrn_orient_matrix_UB_22      0.0913473000
_diffrn_orient_matrix_UB_23      -0.0144729000
_diffrn_orient_matrix_UB_31      -0.0944682000
_diffrn_orient_matrix_UB_32      0.2569156000
_diffrn_orient_matrix_UB_33      -0.0023620000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.340
_reflns_Friedel_fraction_full    0.443
_reflns_Friedel_fraction_max     0.410
_reflns_number_gt                1822
_reflns_number_total             1870
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 462 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.18(12)
_refine_ls_extinction_coef       0.0082(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         1870
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.058
_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)+(0.0600P)²+0.0890P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0949
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C9(H9), C6(H6), C16(H16), C12(H12), C14(H14), C13(H13),
 C15(H15)
1.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.4427(3) 0.2291(3) 0.74067(7) 0.0484(4) Uani 1 1 d . . . . .
O1 O 1.0484(3) 0.4505(4) 0.65850(8) 0.0558(5) Uani 1 1 d . . . . .
N1 N 0.7775(3) 0.4836(4) 0.73627(9) 0.0419(5) Uani 1 1 d . . . . .
N2 N 0.8742(3) 0.6783(4) 0.76761(9) 0.0444(5) Uani 1 1 d . . . . .
C7 C 0.8702(4) 0.3768(5) 0.68191(10) 0.0424(5) Uani 1 1 d . . . . .
C10 C 0.7211(4) 0.7290(5) 0.81301(10) 0.0433(5) Uani 1 1 d . . . . .
C8 C 0.5680(4) 0.4200(5) 0.76241(10) 0.0418(5) Uani 1 1 d . . . . .
C3 C 0.7269(4) 0.1760(4) 0.65832(10) 0.0411(5) Uani 1 1 d . . . . .
C4 C 0.5225(4) 0.1075(4) 0.68813(10) 0.0410(5) Uani 1 1 d . . . . .
C2 C 0.7973(4) 0.0420(4) 0.60561(11) 0.0446(6) Uani 1 1 d . . . . .
H2 H 0.9345 0.0848 0.5856 0.053 Uiso 1 1 calc R U . . .
C1 C 0.6698(4) -0.1510(5) 0.58249(11) 0.0481(6) Uani 1 1 d . . . . .
C11 C 0.7682(4) 0.9240(5) 0.85851(10) 0.0450(5) Uani 1 1 d . . . . .
C5 C 0.3907(4) -0.0868(5) 0.66643(11) 0.0486(6) Uani 1 1 d . . . . .
H5 H 0.2544 -0.1305 0.6867 0.058 Uiso 1 1 calc R U . . .
C9 C 0.5261(4) 0.5711(5) 0.81068(11) 0.0471(6) Uani 1 1 d . . . . .
H9 H 0.3973 0.5720 0.8369 0.057 Uiso 1 1 calc R U . . .
C6 C 0.4650(4) -0.2143(5) 0.61432(12) 0.0498(6) Uani 1 1 d . . . . .
H6 H 0.3775 -0.3457 0.5998 0.060 Uiso 1 1 calc R U . . .
C16 C 0.6102(5) 0.9725(6) 0.90634(12) 0.0572(7) Uani 1 1 d . . . . .
H16 H 0.4735 0.8815 0.9082 0.069 Uiso 1 1 calc R U . . .
C12 C 0.9696(5) 1.0653(5) 0.85675(13) 0.0571(7) Uani 1 1 d . . . . .
H12 H 1.0791 1.0377 0.8255 0.069 Uiso 1 1 calc R U . . .
C14 C 0.8511(5) 1.2890(6) 0.94847(13) 0.0621(7) Uani 1 1 d . . . . .
H14 H 0.8800 1.4097 0.9786 0.075 Uiso 1 1 calc R U . . .
C17 C 0.7475(5) -0.2943(6) 0.52641(13) 0.0637(8) Uani 1 1 d . . . . .
H17A H 0.8117 -0.1904 0.4949 0.096 Uiso 1 1 calc R U . . .
H17B H 0.6142 -0.3784 0.5069 0.096 Uiso 1 1 calc R U . . .
H17C H 0.8663 -0.4061 0.5414 0.096 Uiso 1 1 calc R U . . .
C13 C 1.0073(5) 1.2467(6) 0.90138(14) 0.0648(8) Uani 1 1 d . . . . .
H13 H 1.1412 1.3418 0.8993 0.078 Uiso 1 1 calc R U . . .
C15 C 0.6515(5) 1.1514(6) 0.95066(13) 0.0652(8) Uani 1 1 d . . . . .
H15 H 0.5439 1.1795 0.9823 0.078 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 C8 1.350(3) . ?
O2 C4 1.378(3) . ?
O1 C7 1.214(3) . ?
N1 N2 1.371(3) . ?
N1 C7 1.399(3) . ?
N1 C8 1.375(3) . ?
N2 C10 1.340(3) . ?
C7 C3 1.458(3) . ?
C10 C11 1.459(4) . ?
C10 C9 1.415(3) . ?
C8 C9 1.341(4) . ?
C3 C4 1.393(3) . ?
C3 C2 1.399(3) . ?
C4 C5 1.384(4) . ?
C2 H2 0.9300 . ?
C2 C1 1.375(3) . ?
C1 C6 1.408(3) . ?
C1 C17 1.496(4) . ?
C11 C16 1.394(3) . ?
C11 C12 1.391(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(4) . ?
C9 H9 0.9300 . ?
C6 H6 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.371(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.369(4) . ?
C14 C15 1.372(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C13 H13 0.9300 . ?
C15 H15 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
C8 O2 C4 117.87(16) . . ?
N2 N1 C7 124.31(17) . . ?
N2 N1 C8 110.70(19) . . ?
C8 N1 C7 124.8(2) . . ?
C10 N2 N1 104.05(18) . . ?
O1 C7 N1 121.9(2) . . ?
O1 C7 C3 126.2(2) . . ?
N1 C7 C3 111.99(17) . . ?
N2 C10 C11 120.5(2) . . ?
N2 C10 C9 112.0(2) . . ?
C9 C10 C11 127.5(2) . . ?
O2 C8 N1 121.7(2) . . ?
C9 C8 O2 129.8(2) . . ?
C9 C8 N1 108.5(2) . . ?
C4 C3 C7 121.8(2) . . ?
C4 C3 C2 118.2(2) . . ?
C2 C3 C7 120.04(19) . . ?
O2 C4 C3 121.7(2) . . ?
O2 C4 C5 116.93(19) . . ?
C5 C4 C3 121.4(2) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 C3 122.0(2) . . ?
C1 C2 H2 119.0 . . ?
C2 C1 C6 117.9(2) . . ?
C2 C1 C17 121.6(2) . . ?
C6 C1 C17 120.5(3) . . ?
C16 C11 C10 120.1(2) . . ?
C12 C11 C10 122.3(2) . . ?
C12 C11 C16 117.6(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.9(2) . . ?
C6 C5 H5 120.6 . . ?
C10 C9 H9 127.6 . . ?
C8 C9 C10 104.7(2) . . ?
C8 C9 H9 127.6 . . ?
C1 C6 H6 119.2 . . ?
C5 C6 C1 121.7(2) . . ?
C5 C6 H6 119.2 . . ?
C11 C16 H16 119.2 . . ?
C15 C16 C11 121.5(3) . . ?
C15 C16 H16 119.2 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 120.0 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.3(3) . . ?
C15 C14 H14 120.3 . . ?
C1 C17 H17A 109.5 . . ?
C1 C17 H17B 109.5 . . ?
C1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 H13 119.4 . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?

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
O2 C8 C9 C10 177.6(2) . . . . ?
O2 C4 C5 C6 -179.6(2) . . . . ?
O1 C7 C3 C4 -179.0(2) . . . . ?
O1 C7 C3 C2 3.0(4) . . . . ?
N1 N2 C10 C11 177.83(19) . . . . ?
N1 N2 C10 C9 -0.7(2) . . . . ?
N1 C7 C3 C4 0.4(3) . . . . ?
N1 C7 C3 C2 -177.69(19) . . . . ?
N1 C8 C9 C10 -0.4(3) . . . . ?
N2 N1 C7 O1 0.6(3) . . . . ?
N2 N1 C7 C3 -178.83(19) . . . . ?
N2 N1 C8 O2 -178.23(19) . . . . ?
N2 N1 C8 C9 0.0(3) . . . . ?
N2 C10 C11 C16 -178.8(2) . . . . ?
N2 C10 C11 C12 0.5(3) . . . . ?
N2 C10 C9 C8 0.7(3) . . . . ?
C7 N1 N2 C10 175.7(2) . . . . ?
C7 N1 C8 O2 6.5(3) . . . . ?
C7 N1 C8 C9 -175.3(2) . . . . ?
C7 C3 C4 O2 1.3(3) . . . . ?
C7 C3 C4 C5 -178.4(2) . . . . ?
C7 C3 C2 C1 178.9(2) . . . . ?
C10 C11 C16 C15 178.7(3) . . . . ?
C10 C11 C12 C13 -179.4(2) . . . . ?
C8 O2 C4 C3 0.6(3) . . . . ?
C8 O2 C4 C5 -179.7(2) . . . . ?
C8 N1 N2 C10 0.4(2) . . . . ?
C8 N1 C7 O1 175.2(2) . . . . ?
C8 N1 C7 C3 -4.2(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C3 C2 C1 C6 -1.0(3) . . . . ?
C3 C2 C1 C17 -179.5(2) . . . . ?
C4 O2 C8 N1 -4.3(3) . . . . ?
C4 O2 C8 C9 177.9(2) . . . . ?
C4 C3 C2 C1 0.8(3) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C2 C3 C4 O2 179.4(2) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C2 C1 C6 C5 0.9(4) . . . . ?
C11 C10 C9 C8 -177.7(2) . . . . ?
C11 C16 C15 C14 0.5(5) . . . . ?
C11 C12 C13 C14 1.0(4) . . . . ?
C9 C10 C11 C16 -0.5(4) . . . . ?
C9 C10 C11 C12 178.8(2) . . . . ?
C16 C11 C12 C13 -0.1(4) . . . . ?
C12 C11 C16 C15 -0.6(4) . . . . ?
C17 C1 C6 C5 179.4(2) . . . . ?
C13 C14 C15 C16 0.4(5) . . . . ?
C15 C14 C13 C12 -1.2(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.399
_oxdiff_exptl_absorpt_empirical_full_min 0.592
