# 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 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_20230302b
_database_code_depnum_ccdc_archive 'CCDC 2292057'
loop_
_audit_author_name
_audit_author_address
'mmzhang '
;shantou university
China
;
_audit_update_record             
;
2023-08-31 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;
_audit_creation_date             2023-08-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'CCDC Area Detector'
_chemical_formula_moiety         'C20 H16 N2 O'
_chemical_formula_sum            'C20 H16 N2 O'
_chemical_formula_weight         300.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
_chemical_oxdiff_usercomment     'C H O N'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.69230(10)
_cell_length_b                   11.2384(3)
_cell_length_c                   11.8487(3)
_cell_angle_alpha                109.053(2)
_cell_angle_beta                 93.530(2)
_cell_angle_gamma                92.661(2)
_cell_volume                     713.32(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4819
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      70.8520
_cell_measurement_theta_min      4.7100
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             316
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6217
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.971
_diffrn_reflns_theta_min         3.960
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     54.00  79.00   0.50    0.50    --    0.00  38.00-150.00   50
  2  ω    -57.00 -30.00   0.50    0.50    --    0.00 -38.00-150.00   54
  3  ω    -89.00 -56.00   0.50    0.50    --    0.00 -77.00  90.00   66
  4  ω    -15.00  32.00   0.50    0.50    --    0.00  38.00-150.00   94
  5  ω    -16.00  10.00   0.50    0.50    --    0.00 -38.00-150.00   52
  6  ω    -11.00  21.00   0.50    0.50    --    0.00 -77.00  90.00   64
  7  ω      0.00  44.00   0.50    0.50    --   89.30 -77.00   0.00   88
  8  ω     77.00 103.00   0.50    0.50    --   89.30 -82.00 150.00   52
  9  ω     31.00  86.00   0.50    0.50    --   89.30 -61.00  60.00  110
 10  ω      0.00 108.00   0.50    0.50    --   89.30 -61.00 -90.00  216
 11  ω     22.00 108.00   0.50    0.50    --   89.30 -45.00 120.00  172
 12  ω     85.00 112.00   0.50    0.50    --   89.30 -61.00 -60.00   54
 13  ω     41.00  72.00   0.50    0.50    --   89.30 -82.00 150.00   62
 14  ω      0.00 101.00   0.50    0.50    --   89.30 -30.00  30.00  202
 15  ω     23.00  49.00   0.50    0.50    --   89.30 -61.00 -60.00   52
 16  ω     76.00 120.00   0.50    0.50    --   89.30 -82.00 120.00   88
 17  ω     62.00 113.00   0.50    0.50    --   89.30 -77.00   0.00  102
 18  ω     80.00 147.00   0.50    0.50    --   89.30  30.00-120.00  134
 19  ω     19.00 121.00   0.50    0.50    --   89.30 -82.00 -90.00  204
 20  ω     74.00  99.00   0.50    0.50    --   89.30  61.00-120.00   50
 21  ω     72.00 179.00   0.50    0.50    --   89.30  15.00-180.00  214
;
_diffrn_measurement_device       'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       ?
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0072095000
_diffrn_orient_matrix_UB_12      0.1430742000
_diffrn_orient_matrix_UB_13      0.0221010000
_diffrn_orient_matrix_UB_21      -0.0848140000
_diffrn_orient_matrix_UB_22      0.0217412000
_diffrn_orient_matrix_UB_23      0.1257109000
_diffrn_orient_matrix_UB_31      0.2581582000
_diffrn_orient_matrix_UB_32      0.0139411000
_diffrn_orient_matrix_UB_33      0.0524918000
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_special_details          'CCDC Area Detector'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2488
_reflns_number_total             2634
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.990
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2634
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.057
_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)+(0.0661P)²+0.5015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1270
_refine_special_details          'CCDC Area Detector'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C19(H19), C3(H3), C18(H18), C00C(H00C), C17(H17), C5(H5), C13(H13),
 C16(H16), C15(H15), C11(H11), C12(H12), C1(H1A), C2(H2), C6(H6)
;
_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
O001 O 0.25507(19) 0.11801(11) 0.52857(9) 0.0227(3) Uani 1 1 d . . . . .
N2 N 0.5540(2) 0.26988(12) 0.56955(11) 0.0152(3) Uani 1 1 d . . . . .
N1 N 0.4917(2) 0.33265(11) 0.81205(11) 0.0157(3) Uani 1 1 d . . . . .
H1 H 0.468675 0.356263 0.888773 0.019 Uiso 1 1 calc R U . . .
C14 C 0.5673(3) 0.24456(14) 0.44235(13) 0.0150(3) Uani 1 1 d . . . . .
C8 C 0.3771(3) 0.20304(14) 0.60395(13) 0.0159(3) Uani 1 1 d . . . . .
C7 C 0.3514(3) 0.24487(13) 0.73557(13) 0.0147(3) Uani 1 1 d . . . . .
H7 H 0.243440 0.309833 0.727462 0.018 Uiso 1 1 calc R U . . .
C4 C 0.1609(3) 0.18525(13) 0.78404(13) 0.0156(3) Uani 1 1 d . . . . .
C9 C 0.7126(3) 0.35963(14) 0.65156(13) 0.0152(3) Uani 1 1 d . . . . .
C19 C 0.7361(3) 0.16907(14) 0.38176(13) 0.0172(3) Uani 1 1 d . . . . .
H19 H 0.843881 0.132078 0.422664 0.021 Uiso 1 1 calc R U . . .
C3 C 0.1822(3) 0.20104(14) 0.90650(13) 0.0185(3) Uani 1 1 d . . . . .
H3 H 0.316256 0.247995 0.955136 0.022 Uiso 1 1 calc R U . . .
C18 C 0.7445(3) 0.14856(14) 0.25960(13) 0.0185(3) Uani 1 1 d . . . . .
H18 H 0.859996 0.097797 0.216733 0.022 Uiso 1 1 calc R U . . .
C00C C 0.9034(3) 0.41863(14) 0.61656(14) 0.0177(3) Uani 1 1 d . . . . .
H00C H 0.925992 0.400391 0.533997 0.021 Uiso 1 1 calc R U . . .
C17 C 0.5851(3) 0.20186(14) 0.20029(13) 0.0183(3) Uani 1 1 d . . . . .
H17 H 0.591389 0.186944 0.116896 0.022 Uiso 1 1 calc R U . . .
C5 C -0.0385(3) 0.11531(14) 0.71413(13) 0.0163(3) Uani 1 1 d . . . . .
H5 H -0.055968 0.103187 0.630786 0.020 Uiso 1 1 calc R U . . .
C13 C 0.8342(3) 0.47742(14) 0.85936(13) 0.0183(3) Uani 1 1 d . . . . .
H13 H 0.809070 0.499201 0.941967 0.022 Uiso 1 1 calc R U . . .
C20 C 0.6764(3) 0.38900(13) 0.77367(13) 0.0157(3) Uani 1 1 d . . . . .
C16 C 0.4169(3) 0.27673(15) 0.26194(14) 0.0192(3) Uani 1 1 d . . . . .
H16 H 0.307906 0.313012 0.220951 0.023 Uiso 1 1 calc R U . . .
C15 C 0.4080(3) 0.29856(14) 0.38386(13) 0.0180(3) Uani 1 1 d . . . . .
H15 H 0.293545 0.350126 0.426818 0.022 Uiso 1 1 calc R U . . .
C11 C 1.0587(3) 0.50349(14) 0.70270(14) 0.0195(3) Uani 1 1 d . . . . .
H11 H 1.189703 0.542365 0.678925 0.023 Uiso 1 1 calc R U . . .
C12 C 1.0254(3) 0.53294(14) 0.82471(14) 0.0200(3) Uani 1 1 d . . . . .
H12 H 1.133937 0.590885 0.883280 0.024 Uiso 1 1 calc R U . . .
C1 C -0.1873(3) 0.08031(14) 0.88764(14) 0.0202(3) Uani 1 1 d . . . . .
H1A H -0.305545 0.044995 0.922850 0.024 Uiso 1 1 calc R U . . .
C2 C 0.0102(3) 0.14898(15) 0.95757(13) 0.0211(3) Uani 1 1 d . . . . .
H2 H 0.027142 0.160249 1.040752 0.025 Uiso 1 1 calc R U . . .
C6 C -0.2105(3) 0.06368(14) 0.76610(14) 0.0184(3) Uani 1 1 d . . . . .
H6 H -0.345084 0.016632 0.718066 0.022 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
O001 C8 1.2239(19) . ?
N2 C14 1.4471(18) . ?
N2 C8 1.3875(19) . ?
N2 C9 1.3942(19) . ?
N1 H1 0.8800 . ?
N1 C7 1.299(2) . ?
N1 C20 1.3780(19) . ?
C14 C19 1.386(2) . ?
C14 C15 1.386(2) . ?
C8 C7 1.493(2) . ?
C7 H7 1.0000 . ?
C7 C4 1.488(2) . ?
C4 C3 1.400(2) . ?
C4 C5 1.403(2) . ?
C9 C00C 1.400(2) . ?
C9 C20 1.406(2) . ?
C19 H19 0.9500 . ?
C19 C18 1.394(2) . ?
C3 H3 0.9500 . ?
C3 C2 1.385(2) . ?
C18 H18 0.9500 . ?
C18 C17 1.386(2) . ?
C00C H00C 0.9500 . ?
C00C C11 1.381(2) . ?
C17 H17 0.9500 . ?
C17 C16 1.385(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(2) . ?
C13 H13 0.9500 . ?
C13 C20 1.404(2) . ?
C13 C12 1.379(2) . ?
C16 H16 0.9500 . ?
C16 C15 1.389(2) . ?
C15 H15 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.401(2) . ?
C12 H12 0.9500 . ?
C1 H1A 0.9500 . ?
C1 C2 1.390(2) . ?
C1 C6 1.387(2) . ?
C2 H2 0.9500 . ?
C6 H6 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
C8 N2 C14 117.09(12) . . ?
C8 N2 C9 122.89(12) . . ?
C9 N2 C14 120.02(12) . . ?
C7 N1 H1 119.8 . . ?
C7 N1 C20 120.33(13) . . ?
C20 N1 H1 119.8 . . ?
C19 C14 N2 120.57(13) . . ?
C15 C14 N2 118.04(13) . . ?
C15 C14 C19 121.39(13) . . ?
O001 C8 N2 120.22(13) . . ?
O001 C8 C7 125.05(13) . . ?
N2 C8 C7 114.73(13) . . ?
N1 C7 C8 122.42(13) . . ?
N1 C7 H7 90.1 . . ?
N1 C7 C4 117.30(13) . . ?
C8 C7 H7 90.1 . . ?
C4 C7 C8 120.28(13) . . ?
C4 C7 H7 90.1 . . ?
C3 C4 C7 117.81(13) . . ?
C3 C4 C5 118.51(14) . . ?
C5 C4 C7 123.67(13) . . ?
N2 C9 C00C 122.61(13) . . ?
N2 C9 C20 117.33(13) . . ?
C00C C9 C20 120.06(14) . . ?
C14 C19 H19 120.7 . . ?
C14 C19 C18 118.62(14) . . ?
C18 C19 H19 120.7 . . ?
C4 C3 H3 119.6 . . ?
C2 C3 C4 120.75(14) . . ?
C2 C3 H3 119.6 . . ?
C19 C18 H18 119.8 . . ?
C17 C18 C19 120.35(14) . . ?
C17 C18 H18 119.8 . . ?
C9 C00C H00C 120.2 . . ?
C11 C00C C9 119.64(14) . . ?
C11 C00C H00C 120.2 . . ?
C18 C17 H17 119.8 . . ?
C16 C17 C18 120.38(14) . . ?
C16 C17 H17 119.8 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.37(14) . . ?
C6 C5 H5 119.8 . . ?
C20 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C20 120.60(14) . . ?
N1 C20 C9 121.95(13) . . ?
N1 C20 C13 118.88(13) . . ?
C13 C20 C9 119.17(14) . . ?
C17 C16 H16 120.1 . . ?
C17 C16 C15 119.77(14) . . ?
C15 C16 H16 120.1 . . ?
C14 C15 C16 119.48(14) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C00C C11 H11 119.6 . . ?
C00C C11 C12 120.82(14) . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 119.68(14) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C2 C1 H1A 120.2 . . ?
C6 C1 H1A 120.2 . . ?
C6 C1 C2 119.57(14) . . ?
C3 C2 C1 120.30(14) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C5 C6 H6 119.8 . . ?
C1 C6 C5 120.50(14) . . ?
C1 C6 H6 119.8 . . ?

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
O001 C8 C7 N1 177.37(14) . . . . ?
O001 C8 C7 C4 -2.2(2) . . . . ?
N2 C14 C19 C18 -179.16(13) . . . . ?
N2 C14 C15 C16 179.63(13) . . . . ?
N2 C8 C7 N1 -3.3(2) . . . . ?
N2 C8 C7 C4 177.09(12) . . . . ?
N2 C9 C00C C11 -177.73(13) . . . . ?
N2 C9 C20 N1 -0.4(2) . . . . ?
N2 C9 C20 C13 179.00(12) . . . . ?
N1 C7 C4 C3 -17.1(2) . . . . ?
N1 C7 C4 C5 162.46(14) . . . . ?
C14 N2 C8 O001 7.1(2) . . . . ?
C14 N2 C8 C7 -172.28(12) . . . . ?
C14 N2 C9 C00C -6.9(2) . . . . ?
C14 N2 C9 C20 173.88(13) . . . . ?
C14 C19 C18 C17 -0.6(2) . . . . ?
C8 N2 C14 C19 -102.37(16) . . . . ?
C8 N2 C14 C15 78.06(17) . . . . ?
C8 N2 C9 C00C 174.18(13) . . . . ?
C8 N2 C9 C20 -5.1(2) . . . . ?
C8 C7 C4 C3 162.57(13) . . . . ?
C8 C7 C4 C5 -17.9(2) . . . . ?
C7 N1 C20 C9 3.6(2) . . . . ?
C7 N1 C20 C13 -175.73(13) . . . . ?
C7 C4 C3 C2 179.42(13) . . . . ?
C7 C4 C5 C6 -179.24(13) . . . . ?
C4 C3 C2 C1 -0.2(2) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
C9 N2 C14 C19 78.63(18) . . . . ?
C9 N2 C14 C15 -100.94(16) . . . . ?
C9 N2 C8 O001 -173.95(13) . . . . ?
C9 N2 C8 C7 6.7(2) . . . . ?
C9 C00C C11 C12 -1.1(2) . . . . ?
C19 C14 C15 C16 0.1(2) . . . . ?
C19 C18 C17 C16 0.4(2) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C18 C17 C16 C15 0.1(2) . . . . ?
C00C C9 C20 N1 -179.63(13) . . . . ?
C00C C9 C20 C13 -0.3(2) . . . . ?
C00C C11 C12 C13 -0.5(2) . . . . ?
C17 C16 C15 C14 -0.3(2) . . . . ?
C5 C4 C3 C2 -0.1(2) . . . . ?
C20 N1 C7 C8 -1.7(2) . . . . ?
C20 N1 C7 C4 177.93(12) . . . . ?
C20 C9 C00C C11 1.5(2) . . . . ?
C20 C13 C12 C11 1.8(2) . . . . ?
C15 C14 C19 C18 0.4(2) . . . . ?
C12 C13 C20 N1 178.00(13) . . . . ?
C12 C13 C20 C9 -1.4(2) . . . . ?
C2 C1 C6 C5 -0.1(2) . . . . ?
C6 C1 C2 C3 0.3(2) . . . . ?


_olex2_submission_original_sample_id 'CCDC Area Detector'
_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 1.340
_oxdiff_exptl_absorpt_empirical_full_min 0.454
####################################################################### 
# 
# 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_20230310a
_database_code_depnum_ccdc_archive 'CCDC 2292058'
loop_
_audit_author_name
_audit_author_address
'mmzhang '
;shantou university
China
;
_audit_update_record             
;
2023-08-31 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;
_audit_creation_date             2023-08-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H14 N2 O'
_chemical_formula_sum            'C15 H14 N2 O'
_chemical_formula_weight         238.28
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
_chemical_oxdiff_usercomment     'C H O N'
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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   8.1113(5)
_cell_length_b                   6.7331(3)
_cell_length_c                   11.6092(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.805(7)
_cell_angle_gamma                90.00
_cell_volume                     610.06(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1410
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      69.6540
_cell_measurement_theta_min      6.5350
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic blackish black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             252
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2450
_diffrn_reflns_theta_full        70.57
_diffrn_reflns_theta_max         70.57
_diffrn_reflns_theta_min         3.96
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  26.00   0.50    0.50    --    0.00 -77.00-180.00   78
  2  ω    -88.00 -44.00   0.50    0.50    --    0.00 -77.00-180.00   88
  3  ω    -87.00 -39.00   0.50    0.50    --    0.00 -38.00 -60.00   96
  4  ω     27.00 118.00   0.50    0.50    --   89.30 -82.00  30.00  182
  5  ω     16.00 106.00   0.50    0.50    --   89.30 -15.00 -30.00  180
  6  ω     72.00 120.00   0.50    0.50    --   89.30 -82.00 -90.00   96
  7  ω      8.00 110.00   0.50    0.50    --   89.30 -15.00  60.00  204
  8  ω     59.00  84.00   0.50    0.50    --   89.30 -45.00  90.00   50
  9  ω     28.00 101.00   0.50    0.50    --   89.30 -61.00  30.00  146
;
_diffrn_measurement_device       'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       ?
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1912826000
_diffrn_orient_matrix_UB_12      0.0038543000
_diffrn_orient_matrix_UB_13      0.0696680000
_diffrn_orient_matrix_UB_21      -0.0494012000
_diffrn_orient_matrix_UB_22      -0.0043483000
_diffrn_orient_matrix_UB_23      0.1190161000
_diffrn_orient_matrix_UB_31      0.0046852000
_diffrn_orient_matrix_UB_32      -0.2285274000
_diffrn_orient_matrix_UB_33      -0.0009140000
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1398
_reflns_number_total             1479
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(6)
_refine_ls_extinction_coef       0.0040(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1479
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0537P)²+0.4440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1277
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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 Ternary CH refined with riding coordinates:
 C7C(H7C)
2.b Aromatic/amide H refined with riding coordinates:
 N2N(H2N), N1N(H1N), C13C(H13C), C14C(H14C), C15C(H15C), C4C(H4C), C6C(H6C),
 C2C(H2C), C3C(H3C), C1C(H1C)
2.c Idealised Me refined as rotating group:
 C11C(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1O O 0.5766(3) 0.4819(4) 1.00728(18) 0.0385(6) Uani 1 1 d . . .
N2N N 0.4264(3) 0.6552(5) 0.8466(2) 0.0332(7) Uani 1 1 d . . .
H2N H 0.4137 0.7500 0.8931 0.040 Uiso 1 1 calc R . .
N1N N 0.4457(4) 0.3494(5) 0.6948(3) 0.0456(8) Uani 1 1 d . . .
H1N H 0.4344 0.2474 0.6487 0.055 Uiso 1 1 calc R . .
C8C C 0.5165(4) 0.4934(6) 0.8978(3) 0.0343(8) Uani 1 1 d . . .
C9C C 0.3522(4) 0.6794(5) 0.7229(3) 0.0311(8) Uani 1 1 d . . .
C5C C 0.7383(4) 0.3142(5) 0.8307(3) 0.0314(7) Uani 1 1 d . . .
C10C C 0.3665(4) 0.5251(6) 0.6465(3) 0.0330(8) Uani 1 1 d . . .
C12C C 0.2916(4) 0.5445(6) 0.5223(3) 0.0333(8) Uani 1 1 d . . .
C13C C 0.2010(4) 0.7183(6) 0.4817(3) 0.0379(9) Uani 1 1 d . . .
H13C H 0.1500 0.7331 0.4001 0.045 Uiso 1 1 calc R . .
C14C C 0.1842(5) 0.8688(6) 0.5579(3) 0.0415(9) Uani 1 1 d . . .
H14C H 0.1204 0.9812 0.5278 0.050 Uiso 1 1 calc R . .
C7C C 0.5461(4) 0.3273(6) 0.8182(3) 0.0342(8) Uani 1 1 d . . .
H7C H 0.5112 0.2029 0.8485 0.041 Uiso 1 1 calc R . .
C15C C 0.2629(4) 0.8524(6) 0.6802(3) 0.0365(8) Uani 1 1 d . . .
H15C H 0.2557 0.9552 0.7321 0.044 Uiso 1 1 calc R . .
C4C C 0.8223(5) 0.4709(7) 0.7951(3) 0.0436(9) Uani 1 1 d . . .
H4C H 0.7612 0.5841 0.7629 0.052 Uiso 1 1 calc R . .
C6C C 0.8271(5) 0.1451(6) 0.8787(3) 0.0398(9) Uani 1 1 d . . .
H6C H 0.7700 0.0399 0.9029 0.048 Uiso 1 1 calc R . .
C2C C 1.0852(5) 0.2873(8) 0.8553(4) 0.0600(14) Uani 1 1 d . . .
H2C H 1.2022 0.2785 0.8631 0.072 Uiso 1 1 calc R . .
C11C C 0.3069(5) 0.3825(6) 0.4382(3) 0.0431(9) Uani 1 1 d . . .
H11A H 0.4252 0.3647 0.4406 0.065 Uiso 1 1 calc R . .
H11B H 0.2427 0.4174 0.3584 0.065 Uiso 1 1 calc R . .
H11C H 0.2626 0.2613 0.4615 0.065 Uiso 1 1 calc R . .
C3C C 0.9953(5) 0.4617(8) 0.8066(4) 0.0562(12) Uani 1 1 d . . .
H3C H 1.0521 0.5676 0.7830 0.067 Uiso 1 1 calc R . .
C1C C 1.0033(5) 0.1324(8) 0.8910(3) 0.0546(12) Uani 1 1 d . . .
H1C H 1.0639 0.0190 0.9232 0.065 Uiso 1 1 calc R . .


_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
O1O C8C 1.234(4) . ?
N2N H2N 0.8600 . ?
N2N C8C 1.355(5) . ?
N2N C9C 1.406(4) . ?
N1N H1N 0.8600 . ?
N1N C10C 1.389(5) . ?
N1N C7C 1.450(4) . ?
C8C C7C 1.511(5) . ?
C9C C10C 1.392(5) . ?
C9C C15C 1.390(5) . ?
C5C C7C 1.529(4) . ?
C5C C4C 1.379(5) . ?
C5C C6C 1.381(5) . ?
C10C C12C 1.409(4) . ?
C12C C13C 1.394(5) . ?
C12C C11C 1.491(5) . ?
C13C H13C 0.9300 . ?
C13C C14C 1.375(5) . ?
C14C H14C 0.9300 . ?
C14C C15C 1.393(5) . ?
C7C H7C 0.9800 . ?
C15C H15C 0.9300 . ?
C4C H4C 0.9300 . ?
C4C C3C 1.374(5) . ?
C6C H6C 0.9300 . ?
C6C C1C 1.400(5) . ?
C2C H2C 0.9300 . ?
C2C C3C 1.417(7) . ?
C2C C1C 1.360(7) . ?
C11C H11A 0.9600 . ?
C11C H11B 0.9600 . ?
C11C H11C 0.9600 . ?
C3C H3C 0.9300 . ?
C1C H1C 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
C8C N2N H2N 117.6 . . ?
C8C N2N C9C 124.8(3) . . ?
C9C N2N H2N 117.6 . . ?
C10C N1N H1N 118.0 . . ?
C10C N1N C7C 124.0(3) . . ?
C7C N1N H1N 118.0 . . ?
O1O C8C N2N 121.1(3) . . ?
O1O C8C C7C 120.0(3) . . ?
N2N C8C C7C 118.9(3) . . ?
C10C C9C N2N 118.5(3) . . ?
C15C C9C N2N 119.9(3) . . ?
C15C C9C C10C 121.6(3) . . ?
C4C C5C C7C 120.1(3) . . ?
C4C C5C C6C 120.4(3) . . ?
C6C C5C C7C 119.5(3) . . ?
N1N C10C C9C 119.2(3) . . ?
N1N C10C C12C 121.0(3) . . ?
C9C C10C C12C 119.7(3) . . ?
C10C C12C C11C 120.8(3) . . ?
C13C C12C C10C 117.7(3) . . ?
C13C C12C C11C 121.5(3) . . ?
C12C C13C H13C 118.8 . . ?
C14C C13C C12C 122.4(3) . . ?
C14C C13C H13C 118.8 . . ?
C13C C14C H14C 120.0 . . ?
C13C C14C C15C 119.9(4) . . ?
C15C C14C H14C 120.0 . . ?
N1N C7C C8C 112.8(3) . . ?
N1N C7C C5C 112.6(3) . . ?
N1N C7C H7C 107.7 . . ?
C8C C7C C5C 108.2(3) . . ?
C8C C7C H7C 107.7 . . ?
C5C C7C H7C 107.7 . . ?
C9C C15C C14C 118.6(3) . . ?
C9C C15C H15C 120.7 . . ?
C14C C15C H15C 120.7 . . ?
C5C C4C H4C 119.6 . . ?
C3C C4C C5C 120.7(4) . . ?
C3C C4C H4C 119.6 . . ?
C5C C6C H6C 120.1 . . ?
C5C C6C C1C 119.8(4) . . ?
C1C C6C H6C 120.1 . . ?
C3C C2C H2C 119.5 . . ?
C1C C2C H2C 119.5 . . ?
C1C C2C C3C 121.1(3) . . ?
C12C C11C H11A 109.5 . . ?
C12C C11C H11B 109.5 . . ?
C12C C11C H11C 109.5 . . ?
H11A C11C H11B 109.5 . . ?
H11A C11C H11C 109.5 . . ?
H11B C11C H11C 109.5 . . ?
C4C C3C C2C 118.5(4) . . ?
C4C C3C H3C 120.7 . . ?
C2C C3C H3C 120.7 . . ?
C6C C1C H1C 120.3 . . ?
C2C C1C C6C 119.5(5) . . ?
C2C C1C H1C 120.3 . . ?

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
O1O C8C C7C N1N 171.0(3) . . . . ?
O1O C8C C7C C5C -63.7(4) . . . . ?
N2N C8C C7C N1N -10.3(4) . . . . ?
N2N C8C C7C C5C 115.0(3) . . . . ?
N2N C9C C10C N1N 3.1(4) . . . . ?
N2N C9C C10C C12C 179.3(3) . . . . ?
N2N C9C C15C C14C -177.2(3) . . . . ?
N1N C10C C12C C13C 174.3(3) . . . . ?
N1N C10C C12C C11C -4.7(5) . . . . ?
C8C N2N C9C C10C 2.1(4) . . . . ?
C8C N2N C9C C15C -179.8(3) . . . . ?
C9C N2N C8C O1O -179.3(3) . . . . ?
C9C N2N C8C C7C 2.0(5) . . . . ?
C9C C10C C12C C13C -1.9(4) . . . . ?
C9C C10C C12C C11C 179.2(3) . . . . ?
C5C C4C C3C C2C 0.3(6) . . . . ?
C5C C6C C1C C2C 0.0(5) . . . . ?
C10C N1N C7C C8C 16.1(5) . . . . ?
C10C N1N C7C C5C -106.7(4) . . . . ?
C10C C9C C15C C14C 0.9(5) . . . . ?
C10C C12C C13C C14C 0.5(5) . . . . ?
C12C C13C C14C C15C 1.6(5) . . . . ?
C13C C14C C15C C9C -2.3(5) . . . . ?
C7C N1N C10C C9C -13.0(5) . . . . ?
C7C N1N C10C C12C 170.8(3) . . . . ?
C7C C5C C4C C3C 179.5(3) . . . . ?
C7C C5C C6C C1C -179.7(3) . . . . ?
C15C C9C C10C N1N -175.0(3) . . . . ?
C15C C9C C10C C12C 1.2(5) . . . . ?
C4C C5C C7C N1N 61.8(4) . . . . ?
C4C C5C C7C C8C -63.5(4) . . . . ?
C4C C5C C6C C1C -0.2(5) . . . . ?
C6C C5C C7C N1N -118.6(4) . . . . ?
C6C C5C C7C C8C 116.0(3) . . . . ?
C6C C5C C4C C3C 0.0(5) . . . . ?
C11C C12C C13C C14C 179.4(3) . . . . ?
C3C C2C C1C C6C 0.3(6) . . . . ?
C1C C2C C3C C4C -0.5(6) . . . . ?


_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 1.505
_oxdiff_exptl_absorpt_empirical_full_min 0.652
