# 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. 
# 
#######################################################################

data_416
_database_code_depnum_ccdc_archive 'CCDC 2308832'
loop_
_audit_author_name
_audit_author_address
'Wusheng '
;Frontier Institute of Science and Technology (FIST), Xi an Jiaotong University
China
;
_audit_update_record             
;
2023-11-18 deposited with the CCDC.	2024-02-05 downloaded from the CCDC.
;
_audit_creation_date             2023-05-05
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 N2 O'
_chemical_formula_sum            'C16 H12 N2 O'
_chemical_formula_weight         248.28
_chemical_absolute_configuration ad
_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 0.0181 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   7.96470(10)
_cell_length_b                   10.1591(2)
_cell_length_c                   15.9845(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1293.37(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11194
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.0040
_cell_measurement_theta_min      2.6890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15891
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.663
_diffrn_reflns_theta_min         5.159
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -17.00   1.00    1.00    --  -40.92 -37.00   0.00   98
  2  ω    -67.00  32.00   1.00    1.00    --  -40.92  45.00-135.00   99
  3  ω    -35.00  74.00   1.00    1.00    --   40.92 -77.00 -30.00  109
  4  ω     34.00 121.00   1.00    1.00    --  106.95-125.00 -90.00   87
  5  ω     24.00 109.00   1.00    1.00    --  106.95 -94.00   0.00   85
  6  ω     81.00 178.00   1.00    1.00    --  106.95  45.00-120.00   97
  7  ω     24.00 109.00   1.00    1.00    --  106.95 -94.00  60.00   85
  8  ω     94.00 178.00   1.00    1.00    --  106.95 125.00-120.00   84
  9  ω     34.00 133.00   1.00    1.00    --  106.95 -45.00 -30.00   99
 10  ω   -117.00  -8.00   1.00    1.00    --  -40.92 -77.00 -30.00  109
 11  ω   -113.00 -13.00   1.00    1.00    --  -40.92 -57.00 120.00  100
 12  ω   -113.00 -13.00   1.00    1.00    --  -40.92 -57.00-120.00  100
 13  ω     79.00 178.00   1.00    1.00    --  106.95  30.00 150.00   99
 14  ω     81.00 178.00   1.00    1.00    --  106.95  45.00 -30.00   97
 15  ω     74.00 178.00   1.00    1.00    --  106.95  77.00   0.00  104
 16  ω     78.00 178.00   1.00    1.00    --  106.95  61.00-180.00  100
 17  ω     74.00 178.00   1.00    1.00    --  106.95  77.00 -90.00  104
 18  ω     78.00 178.00   1.00    1.00    --  106.95  61.00  60.00  100
 19  ω   -117.00  -8.00   1.00    1.00    --  -40.92 -77.00  90.00  109
 20  ω   -117.00  -8.00   1.00    1.00    --  -40.92 -77.00-150.00  109
 21  ω     41.00 119.00   1.00    1.00    --   40.92-158.00-149.00   78
 22  ω     31.00  95.00   1.00    1.00    --  106.95 -77.00-180.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1289770000
_diffrn_orient_matrix_UB_12      -0.0726947000
_diffrn_orient_matrix_UB_13      0.0548982000
_diffrn_orient_matrix_UB_21      -0.1417594000
_diffrn_orient_matrix_UB_22      0.0439155000
_diffrn_orient_matrix_UB_23      -0.0592138000
_diffrn_orient_matrix_UB_31      0.0253241000
_diffrn_orient_matrix_UB_32      -0.1257837000
_diffrn_orient_matrix_UB_33      -0.0525667000
_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         0.712
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                2425
_reflns_number_total             2583
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 961 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.13(9)
_refine_ls_extinction_coef       0.0065(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2583
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0291
_refine_ls_restrained_S_all      1.051
_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)+(0.0485P)²+0.0733P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0805
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14)
2.b :
 C16(H16)
;
_atom_sites_solution_hydrogens   mixed
_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 0.70789(15) 0.12444(12) 0.24240(8) 0.0483(3) Uani 1 1 d . . . . .
N1 N 0.49617(16) 0.40361(15) 0.32498(9) 0.0421(3) Uani 1 1 d . . . . .
H1 H 0.445(3) 0.483(2) 0.3073(14) 0.055(6) Uiso 1 1 d . . . . .
N2 N 0.63647(18) 0.17771(14) 0.37474(10) 0.0451(3) Uani 1 1 d . . . . .
H2 H 0.650905 0.095406 0.390316 0.054 Uiso 1 1 calc R U . . .
C1 C 0.52233(19) 0.38837(16) 0.41066(11) 0.0404(4) Uani 1 1 d . . . . .
C2 C 0.4732(2) 0.47987(18) 0.46997(13) 0.0470(4) Uani 1 1 d . . . . .
H2A H 0.429194 0.562436 0.452728 0.056 Uiso 1 1 calc R U . . .
C3 C 0.4881(2) 0.4514(2) 0.55447(13) 0.0517(5) Uani 1 1 d . . . . .
H3 H 0.452104 0.513872 0.594896 0.062 Uiso 1 1 calc R U . . .
C4 C 0.5554(3) 0.3321(2) 0.58031(12) 0.0557(5) Uani 1 1 d . . . . .
H4 H 0.565360 0.312943 0.638274 0.067 Uiso 1 1 calc R U . . .
C5 C 0.6079(2) 0.2412(2) 0.52153(12) 0.0512(4) Uani 1 1 d . . . . .
H5 H 0.655155 0.159807 0.538934 0.061 Uiso 1 1 calc R U . . .
C6 C 0.5912(2) 0.26916(18) 0.43733(11) 0.0429(4) Uani 1 1 d . . . . .
C7 C 0.65930(19) 0.20582(16) 0.29345(11) 0.0410(4) Uani 1 1 d . . . . .
C8 C 0.62323(19) 0.35018(16) 0.26816(11) 0.0390(4) Uani 1 1 d . . . . .
C9 C 0.5519(2) 0.35309(17) 0.17982(11) 0.0431(4) Uani 1 1 d . . . . .
C10 C 0.6333(2) 0.4130(2) 0.11478(11) 0.0512(4) Uani 1 1 d . . . . .
H10 H 0.738867 0.453822 0.124370 0.061 Uiso 1 1 calc R U . . .
C11 C 0.5641(3) 0.4150(2) 0.03468(13) 0.0631(6) Uani 1 1 d . . . . .
H11 H 0.621319 0.458339 -0.009622 0.076 Uiso 1 1 calc R U . . .
C12 C 0.4133(3) 0.3543(2) 0.02012(15) 0.0695(7) Uani 1 1 d . . . . .
H12 H 0.366823 0.353256 -0.034602 0.083 Uiso 1 1 calc R U . . .
C13 C 0.3295(3) 0.2948(2) 0.08549(16) 0.0698(7) Uani 1 1 d . . . . .
H13 H 0.224049 0.254041 0.075505 0.084 Uiso 1 1 calc R U . . .
C14 C 0.3967(2) 0.2934(2) 0.16550(14) 0.0578(5) Uani 1 1 d . . . . .
H14 H 0.337741 0.252210 0.210069 0.069 Uiso 1 1 calc R U . . .
C15 C 0.7869(2) 0.42017(17) 0.27479(11) 0.0422(4) Uani 1 1 d . . . . .
C16 C 0.9173(3) 0.4739(2) 0.28266(12) 0.0532(5) Uani 1 1 d . . . . .
H16 H 1.022327 0.517120 0.288998 0.064 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 1.224(2) . ?
N1 H1 0.95(2) . ?
N1 C1 1.394(2) . ?
N1 C8 1.464(2) . ?
N2 H2 0.8800 . ?
N2 C6 1.412(2) . ?
N2 C7 1.343(2) . ?
C1 C2 1.384(2) . ?
C1 C6 1.396(2) . ?
C2 H2A 0.9500 . ?
C2 C3 1.386(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(3) . ?
C7 C8 1.548(2) . ?
C8 C9 1.523(2) . ?
C8 C15 1.488(2) . ?
C9 C10 1.368(3) . ?
C9 C14 1.396(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.394(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.370(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.180(2) . ?
C16 H16 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
C1 N1 H1 116.9(13) . . ?
C1 N1 C8 117.71(13) . . ?
C8 N1 H1 115.4(14) . . ?
C6 N2 H2 117.3 . . ?
C7 N2 H2 117.3 . . ?
C7 N2 C6 125.47(15) . . ?
N1 C1 C6 117.07(15) . . ?
C2 C1 N1 123.79(16) . . ?
C2 C1 C6 118.97(17) . . ?
C1 C2 H2A 119.9 . . ?
C1 C2 C3 120.20(17) . . ?
C3 C2 H2A 119.9 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.33(18) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.86(19) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.71(18) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 N2 117.04(16) . . ?
C5 C6 N2 122.02(16) . . ?
C5 C6 C1 120.90(16) . . ?
O1 C7 N2 122.97(16) . . ?
O1 C7 C8 121.62(16) . . ?
N2 C7 C8 115.40(14) . . ?
N1 C8 C7 108.52(14) . . ?
N1 C8 C9 108.06(13) . . ?
N1 C8 C15 112.58(13) . . ?
C9 C8 C7 109.25(13) . . ?
C15 C8 C7 105.75(13) . . ?
C15 C8 C9 112.56(14) . . ?
C10 C9 C8 122.44(15) . . ?
C10 C9 C14 119.25(18) . . ?
C14 C9 C8 118.31(17) . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.14(19) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.5(2) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C14 121.1(2) . . ?
C14 C13 H13 119.4 . . ?
C9 C14 H14 120.4 . . ?
C13 C14 C9 119.2(2) . . ?
C13 C14 H14 120.4 . . ?
C16 C15 C8 177.77(19) . . ?
C15 C16 H16 180.0 . . ?

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
O1 C7 C8 N1 152.43(15) . . . . ?
O1 C7 C8 C9 34.8(2) . . . . ?
O1 C7 C8 C15 -86.56(18) . . . . ?
N1 C1 C2 C3 173.32(16) . . . . ?
N1 C1 C6 N2 3.3(2) . . . . ?
N1 C1 C6 C5 -174.34(16) . . . . ?
N1 C8 C9 C10 125.68(17) . . . . ?
N1 C8 C9 C14 -53.6(2) . . . . ?
N2 C7 C8 N1 -28.72(18) . . . . ?
N2 C7 C8 C9 -146.32(14) . . . . ?
N2 C7 C8 C15 92.30(17) . . . . ?
C1 N1 C8 C7 50.22(18) . . . . ?
C1 N1 C8 C9 168.59(14) . . . . ?
C1 N1 C8 C15 -66.48(19) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
C2 C1 C6 N2 178.78(14) . . . . ?
C2 C1 C6 C5 1.1(2) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 N2 -177.39(17) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C6 N2 C7 O1 175.68(16) . . . . ?
C6 N2 C7 C8 -3.2(2) . . . . ?
C6 C1 C2 C3 -1.8(2) . . . . ?
C7 N2 C6 C1 17.8(2) . . . . ?
C7 N2 C6 C5 -164.54(17) . . . . ?
C7 C8 C9 C10 -116.43(18) . . . . ?
C7 C8 C9 C14 64.25(19) . . . . ?
C8 N1 C1 C2 146.08(15) . . . . ?
C8 N1 C1 C6 -38.7(2) . . . . ?
C8 C9 C10 C11 -179.43(16) . . . . ?
C8 C9 C14 C13 -179.93(17) . . . . ?
C9 C10 C11 C12 -1.1(3) . . . . ?
C10 C9 C14 C13 0.7(3) . . . . ?
C10 C11 C12 C13 1.7(3) . . . . ?
C11 C12 C13 C14 -1.1(3) . . . . ?
C12 C13 C14 C9 -0.1(3) . . . . ?
C14 C9 C10 C11 -0.1(3) . . . . ?
C15 C8 C9 C10 0.7(2) . . . . ?
C15 C8 C9 C14 -178.59(15) . . . . ?

_olex2_date_sample_data_collection 2023-05-04
_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 3.417
_oxdiff_exptl_absorpt_empirical_full_min 0.614
