# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_gy1115
_database_code_depnum_ccdc_archive 'CCDC 2242824'
loop_
_audit_author_name
_audit_author_address
'shi xiaotian'
;GUANGDONG PHARMACEUTICAL UNIVERSITY
China
;
_audit_update_record             
;
2023-02-17 deposited with the CCDC.	2023-04-30 downloaded from the CCDC.
;
_audit_creation_date             2023-02-16
_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         'C14 H9 N3'
_chemical_formula_sum            'C14 H9 N3'
_chemical_formula_weight         219.24
_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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.5109(5)
_cell_length_b                   9.7172(8)
_cell_length_c                   19.8992(17)
_cell_angle_alpha                90
_cell_angle_beta                 89.678(8)
_cell_angle_gamma                90
_cell_volume                     1065.60(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1950
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      27.1890
_cell_measurement_theta_min      2.9210
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1229
_diffrn_reflns_av_unetI/netI     0.1080
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5024
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.047
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(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 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00  18.00   1.00    6.00    --  -11.27  19.00-150.00   61
  2  ω     25.00  58.00   1.00    6.00    --  -11.27  19.00-150.00   33
  3  ω     -8.00  29.00   1.00    6.00    --   11.90  57.00 -30.00   37
  4  ω    -34.00  -9.00   1.00    6.00    --  -11.27  38.00   0.00   25
  5  ω     50.00  85.00   1.00    6.00    --   11.90  57.00  90.00   35
  6  ω    -12.00  14.00   1.00    6.00    --   11.90  57.00  90.00   26
;
_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      -0.0308716000
_diffrn_orient_matrix_UB_12      0.0708271000
_diffrn_orient_matrix_UB_13      -0.0004886000
_diffrn_orient_matrix_UB_21      0.0151257000
_diffrn_orient_matrix_UB_22      0.0031984000
_diffrn_orient_matrix_UB_23      0.0353437000
_diffrn_orient_matrix_UB_31      0.1240489000
_diffrn_orient_matrix_UB_32      0.0172800000
_diffrn_orient_matrix_UB_33      -0.0046458000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1427
_reflns_number_total             1890
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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         0.346
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       0.028(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   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1890
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0666
_refine_ls_restrained_S_all      1.053
_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)+(0.0877P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.1805
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13)
;
_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
N1 N -0.0124(3) 0.1234(2) 0.58962(10) 0.0484(6) Uani 1 1 d . . . . .
N2 N 0.6839(3) 0.32444(18) 0.49418(8) 0.0314(5) Uani 1 1 d . . . . .
N3 N 0.6819(3) 0.40890(19) 0.54891(8) 0.0334(5) Uani 1 1 d . . . . .
C1 C 0.4345(3) 0.4415(2) 0.64857(10) 0.0338(6) Uani 1 1 d . . . . .
C2 C 0.2216(4) 0.4206(3) 0.68468(11) 0.0432(6) Uani 1 1 d . . . . .
H2 H 0.104559 0.357025 0.668611 0.052 Uiso 1 1 calc R U . . .
C3 C 0.1779(4) 0.4914(3) 0.74381(12) 0.0499(7) Uani 1 1 d . . . . .
H3 H 0.033122 0.474046 0.768539 0.060 Uiso 1 1 calc R U . . .
C4 C 0.3428(4) 0.5873(3) 0.76741(11) 0.0515(7) Uani 1 1 d . . . . .
H4 H 0.311061 0.637202 0.807568 0.062 Uiso 1 1 calc R U . . .
C5 C 0.5530(5) 0.6088(3) 0.73162(12) 0.0549(8) Uani 1 1 d . . . . .
H5 H 0.667766 0.674131 0.747319 0.066 Uiso 1 1 calc R U . . .
C6 C 0.5999(4) 0.5370(3) 0.67318(11) 0.0457(7) Uani 1 1 d . . . . .
H6 H 0.747122 0.553046 0.649383 0.055 Uiso 1 1 calc R U . . .
C7 C 0.4884(3) 0.3700(2) 0.58498(10) 0.0313(6) Uani 1 1 d . . . . .
C8 C 0.3639(3) 0.2604(2) 0.55328(10) 0.0326(6) Uani 1 1 d . . . . .
C9 C 0.4934(3) 0.2324(2) 0.49440(10) 0.0315(5) Uani 1 1 d . . . . .
C10 C 0.4751(4) 0.1400(2) 0.44026(11) 0.0376(6) Uani 1 1 d . . . . .
H10 H 0.344662 0.076289 0.438151 0.045 Uiso 1 1 calc R U . . .
C11 C 0.6455(4) 0.1434(2) 0.39141(11) 0.0397(6) Uani 1 1 d . . . . .
H11 H 0.633929 0.081557 0.354581 0.048 Uiso 1 1 calc R U . . .
C12 C 0.8411(4) 0.2374(2) 0.39406(10) 0.0398(6) Uani 1 1 d . . . . .
H12 H 0.961558 0.236890 0.359716 0.048 Uiso 1 1 calc R U . . .
C13 C 0.8568(3) 0.3277(2) 0.44536(10) 0.0344(6) Uani 1 1 d . . . . .
H13 H 0.986136 0.392199 0.447262 0.041 Uiso 1 1 calc R U . . .
C14 C 0.1558(4) 0.1856(2) 0.57415(10) 0.0367(6) 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
N1 C14 1.148(3) . ?
N2 N3 1.364(2) . ?
N2 C9 1.379(3) . ?
N2 C13 1.357(2) . ?
N3 C7 1.336(2) . ?
C1 C2 1.387(3) . ?
C1 C6 1.392(3) . ?
C1 C7 1.472(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.372(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.417(3) . ?
C8 C9 1.395(3) . ?
C8 C14 1.417(3) . ?
C9 C10 1.406(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.348(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.414(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.349(3) . ?
C13 H13 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
N3 N2 C9 112.63(15) . . ?
C13 N2 N3 124.07(16) . . ?
C13 N2 C9 123.29(17) . . ?
C7 N3 N2 105.18(16) . . ?
C2 C1 C6 118.0(2) . . ?
C2 C1 C7 122.8(2) . . ?
C6 C1 C7 119.19(19) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.7(2) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.9(3) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 120.9(2) . . ?
C5 C6 H6 119.5 . . ?
N3 C7 C1 119.00(19) . . ?
N3 C7 C8 111.10(17) . . ?
C8 C7 C1 129.90(18) . . ?
C7 C8 C14 130.35(19) . . ?
C9 C8 C7 105.87(17) . . ?
C9 C8 C14 123.8(2) . . ?
N2 C9 C8 105.22(18) . . ?
N2 C9 C10 118.00(18) . . ?
C8 C9 C10 136.79(19) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 118.96(19) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.1(2) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.03(19) . . ?
C13 C12 H12 120.0 . . ?
N2 C13 H13 120.7 . . ?
C12 C13 N2 118.59(19) . . ?
C12 C13 H13 120.7 . . ?
N1 C14 C8 178.4(2) . . ?

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
N2 N3 C7 C1 179.61(15) . . . . ?
N2 N3 C7 C8 -0.3(2) . . . . ?
N2 C9 C10 C11 1.2(3) . . . . ?
N3 N2 C9 C8 -0.3(2) . . . . ?
N3 N2 C9 C10 179.70(16) . . . . ?
N3 N2 C13 C12 179.03(18) . . . . ?
N3 C7 C8 C9 0.1(2) . . . . ?
N3 C7 C8 C14 178.2(2) . . . . ?
C1 C2 C3 C4 1.7(4) . . . . ?
C1 C7 C8 C9 -179.79(19) . . . . ?
C1 C7 C8 C14 -1.7(4) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C2 C1 C7 N3 171.33(19) . . . . ?
C2 C1 C7 C8 -8.8(3) . . . . ?
C2 C3 C4 C5 -1.3(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
C6 C1 C2 C3 -1.0(3) . . . . ?
C6 C1 C7 N3 -6.9(3) . . . . ?
C6 C1 C7 C8 173.0(2) . . . . ?
C7 C1 C2 C3 -179.2(2) . . . . ?
C7 C1 C6 C5 178.2(2) . . . . ?
C7 C8 C9 N2 0.2(2) . . . . ?
C7 C8 C9 C10 -179.9(2) . . . . ?
C8 C9 C10 C11 -178.7(2) . . . . ?
C9 N2 N3 C7 0.4(2) . . . . ?
C9 N2 C13 C12 0.6(3) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 C13 -1.4(3) . . . . ?
C11 C12 C13 N2 1.0(3) . . . . ?
C13 N2 N3 C7 -178.20(17) . . . . ?
C13 N2 C9 C8 178.26(17) . . . . ?
C13 N2 C9 C10 -1.7(3) . . . . ?
C14 C8 C9 N2 -178.13(18) . . . . ?
C14 C8 C9 C10 1.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 1.249
_oxdiff_exptl_absorpt_empirical_full_min 0.656
