# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2149708'
loop_
_audit_author_name
_audit_author_address
'Min Zhang'
;Jiangsu University
China
;
_audit_update_record             
;
2022-02-03 deposited with the CCDC.	2022-06-14 downloaded from the CCDC.
;
_audit_creation_date             2022-02-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H8 N2 O2'
_chemical_formula_sum            'C15 H8 N2 O2'
_chemical_formula_weight         248.23
_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'
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'
H H 0.0000 0.0000 '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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.4100(15)
_cell_length_b                   7.6000(15)
_cell_length_c                   19.460(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.52(3)
_cell_angle_gamma                90
_cell_volume                     1095.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4426
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7687
_cell_measurement_theta_min      2.8769
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'Absorption correction given as multi-scan'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4715
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.402
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1314
_reflns_number_total             1989
_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       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        ?
_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    ?
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.207
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1989
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1316
_refine_ls_R_factor_gt           0.0829
_refine_ls_restrained_S_all      1.207
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0774P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1748
_refine_ls_wR_factor_ref         0.2018
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C11(H11), C12(H12), C1(H1), C3(H3), C16(H16), C13(H13), C2(H2)
;
_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
C8 C 0.7920(5) 0.8773(4) -0.03747(18) 0.0424(9) Uani 1 1 d . . . . .
C10 C 0.8010(5) 0.8957(4) 0.10134(18) 0.0414(9) Uani 1 1 d . . . . .
C15 C 0.7290(5) 1.0508(5) 0.0643(2) 0.0455(9) Uani 1 1 d . . . . .
C6 C 0.6800(4) 1.1574(5) -0.05780(19) 0.0423(9) Uani 1 1 d . . . . .
C9 C 0.8564(5) 0.7456(4) 0.06511(19) 0.0423(9) Uani 1 1 d . . . . .
C14 C 0.9199(5) 0.5987(5) 0.1018(2) 0.0507(10) Uani 1 1 d . . . . .
H14 H 0.957586 0.499110 0.078410 0.061 Uiso 1 1 calc R U . . .
C11 C 0.8123(5) 0.8957(5) 0.1725(2) 0.0496(10) Uani 1 1 d . . . . .
H11 H 0.776348 0.994694 0.196646 0.059 Uiso 1 1 calc R U . . .
C12 C 0.8763(5) 0.7503(5) 0.2079(2) 0.0562(11) Uani 1 1 d . . . . .
H12 H 0.885638 0.752080 0.255674 0.067 Uiso 1 1 calc R U . . .
C1 C 0.6193(5) 1.3288(5) -0.0496(2) 0.0493(10) Uani 1 1 d . . . . .
H1 H 0.606419 1.378492 -0.006339 0.059 Uiso 1 1 calc R U . . .
C5 C 0.7023(4) 1.0848(5) -0.12195(18) 0.0424(9) Uani 1 1 d . . . . .
C7 C 0.7735(5) 0.9049(5) -0.1132(2) 0.0493(10) Uani 1 1 d . . . . .
C3 C 0.5987(5) 1.3519(5) -0.1731(2) 0.0534(11) Uani 1 1 d . . . . .
H3 H 0.568536 1.418590 -0.211753 0.064 Uiso 1 1 calc R U . . .
C16 C 0.6639(5) 1.1813(5) -0.1807(2) 0.0508(10) Uani 1 1 d . . . . .
H16 H 0.681052 1.133786 -0.224111 0.061 Uiso 1 1 calc R U . . .
C13 C 0.9265(5) 0.6015(5) 0.1719(2) 0.0561(11) Uani 1 1 d . . . . .
H13 H 0.965303 0.502072 0.195928 0.067 Uiso 1 1 calc R U . . .
C2 C 0.5789(5) 1.4216(5) -0.1092(2) 0.0529(11) Uani 1 1 d . . . . .
H2 H 0.536477 1.536277 -0.105556 0.063 Uiso 1 1 calc R U . . .
N1 N 0.7337(4) 1.0332(3) -0.00576(14) 0.0401(8) Uani 1 1 d . . . . .
N2 N 0.8514(4) 0.7395(4) -0.00629(16) 0.0470(8) Uani 1 1 d . . . . .
O1 O 0.8134(4) 0.7978(4) -0.15667(14) 0.0691(9) Uani 1 1 d . . . . .
O2 O 0.6664(4) 1.1819(3) 0.09169(13) 0.0626(8) Uani 1 1 d . . . . .


_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
C8 C7 1.492(5) . ?
C8 N1 1.408(4) . ?
C8 N2 1.283(4) . ?
C10 C15 1.475(5) . ?
C10 C9 1.408(5) . ?
C10 C11 1.385(5) . ?
C15 N1 1.371(4) . ?
C15 O2 1.227(4) . ?
C6 C1 1.388(5) . ?
C6 C5 1.379(5) . ?
C6 N1 1.433(4) . ?
C9 C14 1.401(5) . ?
C9 N2 1.390(5) . ?
C14 H14 0.9300 . ?
C14 C13 1.363(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.384(5) . ?
C5 C7 1.474(5) . ?
C5 C16 1.382(5) . ?
C7 O1 1.216(4) . ?
C3 H3 0.9300 . ?
C3 C16 1.393(5) . ?
C3 C2 1.362(5) . ?
C16 H16 0.9300 . ?
C13 H13 0.9300 . ?
C2 H2 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
N1 C8 C7 107.1(3) . . ?
N2 C8 C7 127.1(3) . . ?
N2 C8 N1 125.8(3) . . ?
C9 C10 C15 120.6(3) . . ?
C11 C10 C15 120.0(3) . . ?
C11 C10 C9 119.3(3) . . ?
N1 C15 C10 112.9(3) . . ?
O2 C15 C10 124.9(3) . . ?
O2 C15 N1 122.1(3) . . ?
C1 C6 N1 128.4(3) . . ?
C5 C6 C1 121.8(3) . . ?
C5 C6 N1 109.8(3) . . ?
C14 C9 C10 119.3(4) . . ?
N2 C9 C10 121.9(3) . . ?
N2 C9 C14 118.9(3) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 C9 120.0(4) . . ?
C13 C14 H14 120.0 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.6(4) . . ?
C13 C12 H12 120.2 . . ?
C6 C1 H1 121.8 . . ?
C2 C1 C6 116.4(4) . . ?
C2 C1 H1 121.8 . . ?
C6 C5 C7 108.6(3) . . ?
C6 C5 C16 120.6(3) . . ?
C16 C5 C7 130.8(4) . . ?
C5 C7 C8 105.5(3) . . ?
O1 C7 C8 125.1(3) . . ?
O1 C7 C5 129.4(4) . . ?
C16 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C16 120.4(3) . . ?
C5 C16 C3 118.0(4) . . ?
C5 C16 H16 121.0 . . ?
C3 C16 H16 121.0 . . ?
C14 C13 C12 121.0(4) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C1 C2 H2 118.6 . . ?
C3 C2 C1 122.7(4) . . ?
C3 C2 H2 118.6 . . ?
C8 N1 C6 109.1(3) . . ?
C15 N1 C8 122.3(3) . . ?
C15 N1 C6 128.6(3) . . ?
C8 N2 C9 116.4(3) . . ?

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
C10 C15 N1 C8 3.5(4) . . . . ?
C10 C15 N1 C6 -178.2(3) . . . . ?
C10 C9 C14 C13 0.4(5) . . . . ?
C10 C9 N2 C8 -0.6(5) . . . . ?
C10 C11 C12 C13 -1.2(6) . . . . ?
C15 C10 C9 C14 -178.4(3) . . . . ?
C15 C10 C9 N2 2.2(5) . . . . ?
C15 C10 C11 C12 178.8(3) . . . . ?
C6 C1 C2 C3 -0.8(6) . . . . ?
C6 C5 C7 C8 -0.1(4) . . . . ?
C6 C5 C7 O1 -179.1(4) . . . . ?
C6 C5 C16 C3 -1.4(5) . . . . ?
C9 C10 C15 N1 -3.5(5) . . . . ?
C9 C10 C15 O2 174.8(3) . . . . ?
C9 C10 C11 C12 -0.3(5) . . . . ?
C9 C14 C13 C12 -2.0(6) . . . . ?
C14 C9 N2 C8 179.9(3) . . . . ?
C11 C10 C15 N1 177.4(3) . . . . ?
C11 C10 C15 O2 -4.3(6) . . . . ?
C11 C10 C9 C14 0.7(5) . . . . ?
C11 C10 C9 N2 -178.7(3) . . . . ?
C11 C12 C13 C14 2.4(6) . . . . ?
C1 C6 C5 C7 178.1(3) . . . . ?
C1 C6 C5 C16 -0.2(5) . . . . ?
C1 C6 N1 C8 -177.9(4) . . . . ?
C1 C6 N1 C15 3.7(6) . . . . ?
C5 C6 C1 C2 1.2(5) . . . . ?
C5 C6 N1 C8 0.1(4) . . . . ?
C5 C6 N1 C15 -178.3(3) . . . . ?
C7 C8 N1 C15 178.4(3) . . . . ?
C7 C8 N1 C6 -0.2(4) . . . . ?
C7 C8 N2 C9 179.7(3) . . . . ?
C7 C5 C16 C3 -179.3(3) . . . . ?
C16 C5 C7 C8 178.0(3) . . . . ?
C16 C5 C7 O1 -1.0(7) . . . . ?
C16 C3 C2 C1 -0.8(6) . . . . ?
C2 C3 C16 C5 1.8(5) . . . . ?
N1 C8 C7 C5 0.2(4) . . . . ?
N1 C8 C7 O1 179.2(4) . . . . ?
N1 C8 N2 C9 0.6(5) . . . . ?
N1 C6 C1 C2 179.0(3) . . . . ?
N1 C6 C5 C7 0.0(4) . . . . ?
N1 C6 C5 C16 -178.3(3) . . . . ?
N2 C8 C7 C5 -179.1(3) . . . . ?
N2 C8 C7 O1 -0.1(6) . . . . ?
N2 C8 N1 C15 -2.4(5) . . . . ?
N2 C8 N1 C6 179.1(3) . . . . ?
N2 C9 C14 C13 179.9(3) . . . . ?
O2 C15 N1 C8 -174.8(3) . . . . ?
O2 C15 N1 C6 3.4(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
