# 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_ptp-pe293_auto_2
_database_code_depnum_ccdc_archive 'CCDC 2206056'
loop_
_audit_author_name
_audit_author_address
'KAKOLI MAJI'
;INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH KOLKATA
India
;
_audit_update_record             
;
2022-09-08 deposited with the CCDC.	2022-12-06 downloaded from the CCDC.
;
_audit_creation_date             2022-09-08
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 N3'
_chemical_formula_sum            'C12 H9 N3'
_chemical_formula_weight         195.22
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N'
_chemical_oxdiff_usercomment     100K
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'

_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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   8.10200(10)
_cell_length_b                   10.5530(2)
_cell_length_c                   10.6731(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     912.55(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7031
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      68.1880
_cell_measurement_theta_min      4.1120
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_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       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6186
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.298
_diffrn_reflns_theta_min         4.189
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     77.00 164.00   0.50    0.20    --   96.67  54.00  15.00  174
  2  ω     78.00 163.00   0.50    0.20    --   96.67  50.00  60.00  170
  3  ω     80.00 163.00   0.50    0.20    --   96.67  42.00 120.00  166
  4  ω     75.00 164.00   0.50    0.20    --   96.67  59.00 150.00  178
  5  ω     82.00 167.00   0.50    0.20    --   96.67  25.00 -30.00  170
  6  ω     70.00 165.00   0.50    0.20    --   96.67  77.00-133.00  190
  7  ω     30.00  57.00   0.50    0.20    --   96.67 -50.00   0.00   54
  8  ω     28.00 105.00   0.50    0.20    --   96.67 -77.00 100.00  154
  9  ω     29.00  68.00   0.50    0.20    --   96.67 -59.00 150.00   78
 10  ω     30.00  57.00   0.50    0.20    --   96.67 -50.00 120.00   54
 11  ω     29.00  83.00   0.50    0.20    --   96.67 -68.00   0.00  108
 12  ω     30.00  57.00   0.50    0.20    --   96.67 -50.00  90.00   54
 13  ω     30.00  57.00   0.50    0.20    --   96.67 -50.00  30.00   54
 14  ω     30.00  57.00   0.50    0.20    --   96.67 -50.00-120.00   54
 15  ω     30.00  62.00   0.50    0.20    --   96.67 -54.00-128.00   64
 16  ω     30.00  57.00   0.50    0.20    --   96.67 -50.00-180.00   54
 17  ω     41.00  99.00   0.50    0.20    --   40.33-138.00 -30.00  116
 18  ω     -8.00  74.00   0.50    0.20    --   40.33 -96.00   4.00  164
 19  ω    -28.00  67.00   0.50    0.20    --   40.33 -77.00 100.00  190
 20  ω    105.00 170.00   0.50    0.20    --   96.67  96.00  60.00  130
 21  ω     22.00 106.00   0.50    0.20    --   96.67 -96.00   4.00  168
 22  ω    -26.00  61.00   0.50    0.20    --   40.33 -54.00-128.00  174
 23  ω   -106.00 -25.00   0.50    0.20    --  -40.33 -38.00   0.00  162
 24  ω   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00  30.00  192
 25  ω   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00 100.00  192
 26  ω   -108.00 -17.00   0.50    0.20    --  -40.33 -64.00 150.00  182
 27  ω   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00 -60.00  192
 28  ω   -107.00 -20.00   0.50    0.20    --  -40.33 -54.00-128.00  174
 29  ω   -109.00 -13.00   0.50    0.20    --  -40.33 -77.00-150.00  192
 30  ω   -107.00 -21.00   0.50    0.20    --  -40.33 -50.00 -60.00  172
 31  ω    -80.00  -9.00   0.50    0.20    --  -82.50  96.00 113.00  142
 32  ω    -74.00  30.00   0.50    0.20    --  -40.33  96.00 113.00  208
 33  ω    -24.00  35.00   0.50    0.20    --  -40.33  12.00   0.00  118
 34  ω    -60.00  27.00   0.50    0.20    --  -40.33  54.00  15.00  174
 35  ω   -105.00 -14.00   0.50    0.20    --  -82.50  77.00-133.00  182
 36  ω    -47.00 -15.00   0.50    0.20    --  -82.50  42.00-120.00   64
 37  ω   -149.00 -62.00   0.50    0.20    --  -82.50 -54.00-128.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0685683000
_diffrn_orient_matrix_UB_12      0.1180404000
_diffrn_orient_matrix_UB_13      -0.0671408000
_diffrn_orient_matrix_UB_21      -0.1033928000
_diffrn_orient_matrix_UB_22      -0.0325356000
_diffrn_orient_matrix_UB_23      -0.1167619000
_diffrn_orient_matrix_UB_31      -0.1441557000
_diffrn_orient_matrix_UB_32      0.0794456000
_diffrn_orient_matrix_UB_33      0.0518687000
_diffrn_oxdiff_digest_frames     
;
015aa2ec32835174e25df1bc9792af0d4b05238d75f
;
_diffrn_oxdiff_digest_hkl        
;
017f43de7b5dddc013805cd82f77b0c2e0e365
;
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    0.855
_reflns_Friedel_fraction_max     0.846
_reflns_number_gt                1524
_reflns_number_total             1541
_reflns_odcompleteness_completeness 94.19
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 632 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(7)
_refine_ls_extinction_coef       0.018(2)
_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   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1541
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      1.056
_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)+(0.0852P)²+0.1266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1146
_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:
 C8(H8), C5(H5), C12(H12), C11(H11), C9(H9), C2(H2), C4(H4), C3(H3), C10(H10)
;
_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 0.4075(3) 0.43595(19) 0.5242(2) 0.0147(5) Uani 1 1 d . . . . .
N2 N 0.3004(3) 0.2946(2) 0.6521(2) 0.0171(5) Uani 1 1 d . . . . .
N3 N 0.2470(3) 0.4120(2) 0.6919(2) 0.0175(5) Uani 1 1 d . . . . .
C8 C 0.5090(3) 0.2022(2) 0.3614(3) 0.0168(6) Uani 1 1 d . . . . .
H8 H 0.469802 0.269509 0.310283 0.020 Uiso 1 1 calc R . . . .
C1 C 0.3120(3) 0.4968(2) 0.6146(2) 0.0152(6) Uani 1 1 d . . . . .
C6 C 0.3962(3) 0.3088(2) 0.5532(3) 0.0157(6) Uani 1 1 d . . . . .
C7 C 0.4825(3) 0.2047(2) 0.4899(3) 0.0149(6) Uani 1 1 d . . . . .
C5 C 0.4958(3) 0.5034(2) 0.4348(3) 0.0158(6) Uani 1 1 d . . . . .
H5 H 0.563350 0.460763 0.375514 0.019 Uiso 1 1 calc R . . . .
C12 C 0.5398(3) 0.1046(2) 0.5642(3) 0.0172(6) Uani 1 1 d . . . . .
H12 H 0.522851 0.106512 0.652263 0.021 Uiso 1 1 calc R . . . .
C11 C 0.6215(3) 0.0023(2) 0.5101(3) 0.0196(7) Uani 1 1 d . . . . .
H11 H 0.658038 -0.066286 0.560681 0.024 Uiso 1 1 calc R . . . .
C9 C 0.5932(3) 0.1011(2) 0.3077(3) 0.0191(6) Uani 1 1 d . . . . .
H9 H 0.612543 0.100125 0.219914 0.023 Uiso 1 1 calc R . . . .
C2 C 0.2989(3) 0.6295(3) 0.6125(2) 0.0177(6) Uani 1 1 d . . . . .
H2 H 0.233280 0.672656 0.672663 0.021 Uiso 1 1 calc R . . . .
C4 C 0.4835(3) 0.6309(2) 0.4341(2) 0.0170(6) Uani 1 1 d . . . . .
H4 H 0.543436 0.678420 0.373734 0.020 Uiso 1 1 calc R . . . .
C3 C 0.3821(3) 0.6954(2) 0.5225(3) 0.0182(6) Uani 1 1 d . . . . .
H3 H 0.372226 0.785056 0.518657 0.022 Uiso 1 1 calc R . . . .
C10 C 0.6493(3) 0.0011(2) 0.3814(3) 0.0201(7) Uani 1 1 d . . . . .
H10 H 0.706511 -0.067725 0.343974 0.024 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
N1 C1 1.394(4) . ?
N1 C6 1.380(3) . ?
N1 C5 1.389(4) . ?
N2 N3 1.379(3) . ?
N2 C6 1.319(4) . ?
N3 C1 1.327(4) . ?
C8 C7 1.388(4) . ?
C8 C9 1.390(4) . ?
C1 C2 1.405(4) . ?
C6 C7 1.467(4) . ?
C7 C12 1.401(3) . ?
C5 C4 1.349(4) . ?
C12 C11 1.391(4) . ?
C11 C10 1.392(4) . ?
C9 C10 1.392(4) . ?
C2 C3 1.364(4) . ?
C4 C3 1.424(4) . ?

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
C6 N1 C1 104.9(2) . . ?
C6 N1 C5 133.3(2) . . ?
C5 N1 C1 121.7(2) . . ?
C6 N2 N3 109.2(2) . . ?
C1 N3 N2 106.9(2) . . ?
C7 C8 C9 119.8(2) . . ?
N1 C1 C2 119.3(2) . . ?
N3 C1 N1 109.8(2) . . ?
N3 C1 C2 130.8(2) . . ?
N1 C6 C7 126.4(2) . . ?
N2 C6 N1 109.2(2) . . ?
N2 C6 C7 124.3(2) . . ?
C8 C7 C6 122.9(2) . . ?
C8 C7 C12 119.6(2) . . ?
C12 C7 C6 117.5(2) . . ?
C4 C5 N1 118.5(3) . . ?
C11 C12 C7 120.5(3) . . ?
C12 C11 C10 119.6(3) . . ?
C8 C9 C10 120.6(3) . . ?
C3 C2 C1 118.9(2) . . ?
C5 C4 C3 121.1(3) . . ?
C2 C3 C4 120.5(2) . . ?
C11 C10 C9 119.9(2) . . ?

_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 2.674
_oxdiff_exptl_absorpt_empirical_full_min 0.673
