# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_n-11-r-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2456403'
loop_
_audit_author_name
_audit_author_address
'Vijay Kumar Das'
;Banaras Hindu University
India
;
_audit_update_record             
;
2025-06-04 deposited with the CCDC.	2026-05-27 downloaded from the CCDC.
;
_audit_creation_date             2025-04-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7217)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        1H-Indole-3-carbonitrile
_chemical_formula_moiety         'C9 H6 N2'
_chemical_formula_sum            'C9 H6 N2'
_chemical_formula_weight         142.16
_chemical_absolute_configuration ?
_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'

_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                   13.9424(4)
_cell_length_b                   5.9908(2)
_cell_length_c                   8.9036(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     743.68(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4229
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.6050
_cell_measurement_theta_min      3.1380
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.912
_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7801
_diffrn_reflns_point_group_measured_fraction_full 0.881
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.027
_diffrn_reflns_theta_min         6.349
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00 117.00   0.50    0.20    --   40.58  10.00  88.00  234
  2  ω     17.00 108.00   0.50    0.20    --   40.58  65.00 120.00  182
  3  ω     14.00 109.00   0.50    0.20    --   40.58  77.00  30.00  190
  4  ω     14.00 109.00   0.50    0.20    --   40.58  77.00 -30.00  190
  5  ω     81.00 164.00   0.50    0.61    --   96.04 145.00 -90.00  166
  6  ω     99.00 160.00   0.50    0.61    --   96.04 117.00   0.00  122
  7  ω     88.00 163.00   0.50    0.61    --   96.04 135.00 123.00  150
  8  ω     98.00 160.00   0.50    0.61    --   96.04 119.00-136.00  124
  9  ω     99.00 160.00   0.50    0.61    --   96.04 117.00-180.00  122
 10  ω     72.00 164.00   0.50    0.61    --   96.04  68.00 -90.00  184
 11  ω     77.00 163.00   0.50    0.61    --   96.04  50.00-180.00  172
 12  ω     72.00 164.00   0.50    0.61    --   96.04  68.00  30.00  184
 13  ω     55.00 173.00   0.50    0.61    --   96.04  10.00  88.00  236
 14  ω     79.00 162.00   0.50    0.61    --   96.04  42.00   0.00  166
 15  ω     82.00 164.00   0.50    0.61    --   96.04  33.00-120.00  164
 16  ω     72.00 164.00   0.50    0.61    --   96.04  68.00  60.00  184
 17  ω     74.00 163.00   0.50    0.61    --   96.04  59.00 120.00  178
 18  ω     28.00  68.00   0.50    0.61    --   96.04 -59.00 120.00   80
 19  ω     29.00  57.00   0.50    0.61    --   96.04 -50.00  90.00   56
 20  ω     28.00  68.00   0.50    0.61    --   96.04 -59.00   0.00   80
 21  ω     28.00  68.00   0.50    0.61    --   96.04 -59.00-120.00   80
 22  ω     29.00  57.00   0.50    0.61    --   96.04 -50.00 -90.00   56
 23  ω     26.00 127.00   0.50    0.61    --   96.04 -87.00-150.00  202
 24  ω     39.00 120.00   0.50    0.61    --   96.04-135.00  58.00  162
 25  ω     33.00 110.00   0.50    0.61    --   96.04-119.00 138.00  154
 26  ω     30.00  85.00   0.50    0.20    --   40.58-119.00 138.00  110
 27  ω   -117.00  -3.00   0.50    0.20    --  -40.58 -10.00 -85.00  228
 28  ω   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00-120.00  190
 29  ω   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00  60.00  190
 30  ω   -108.00 -17.00   0.50    0.20    --  -40.58 -65.00 120.00  182
 31  ω   -108.00 -17.00   0.50    0.20    --  -40.58 -65.00 -90.00  182
 32  ω   -107.00 -20.00   0.50    0.20    --  -40.58 -54.00-180.00  174
 33  ω    -94.00 -18.00   0.50    0.61    --  -82.50 135.00 123.00  152
 34  ω    -94.00 -18.00   0.50    0.20    --  -40.58 135.00 123.00  152
 35  ω    -61.00  26.00   0.50    0.20    --  -40.58  54.00 -30.00  174
 36  ω    -47.00 -15.00   0.50    0.61    --  -82.50  42.00 120.00   64
 37  ω    -24.00  35.00   0.50    0.20    --  -40.58  11.00  60.00  118
 38  ω    -28.00  31.00   0.50    0.20    --  -40.58  21.00-180.00  118
 39  ω   -159.00 -45.00   0.50    0.61    --  -82.50 -10.00 -85.00  228
 40  ω   -151.00 -55.00   0.50    0.61    --  -82.50 -77.00-180.00  192
 41  ω   -109.00 -50.00   0.50    0.20    --  -40.58-158.00 -15.00  118
;
_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      -0.0020474000
_diffrn_orient_matrix_UB_12      -0.2547671000
_diffrn_orient_matrix_UB_13      -0.0232618000
_diffrn_orient_matrix_UB_21      0.1104511000
_diffrn_orient_matrix_UB_22      -0.0045951000
_diffrn_orient_matrix_UB_23      -0.0017007000
_diffrn_orient_matrix_UB_31      0.0008159000
_diffrn_orient_matrix_UB_32      -0.0347375000
_diffrn_orient_matrix_UB_33      0.1714749000
_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         0.650
_reflns_Friedel_fraction_full    0.751
_reflns_Friedel_fraction_max     0.745
_reflns_number_gt                1079
_reflns_number_total             1188
_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 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 385 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1188
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.144
_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)+(0.0468P)²+0.0653P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0978
_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:
 N1(H1), C1(H1A), C5(H5), C7(H7), C6(H6), C8(H8)
;
_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 0.30809(18) 0.4391(4) 0.4035(3) 0.0740(7) Uani 1 1 d . . . . .
H1 H 0.294262 0.313071 0.362624 0.089 Uiso 1 1 calc R U . . .
C2 C 0.2959(2) 0.7455(4) 0.5414(4) 0.0573(7) Uani 1 1 d . . . . .
N2 N 0.2288(2) 1.0575(4) 0.7091(4) 0.0811(9) Uani 1 1 d . . . . .
C4 C 0.38750(18) 0.7503(4) 0.4684(3) 0.0548(7) Uani 1 1 d . . . . .
C9 C 0.3925(2) 0.5542(4) 0.3821(4) 0.0605(7) Uani 1 1 d . . . . .
C1 C 0.2503(2) 0.5527(4) 0.4977(4) 0.0674(8) Uani 1 1 d . . . . .
H1A H 0.189431 0.507989 0.528206 0.081 Uiso 1 1 calc R U . . .
C3 C 0.2568(2) 0.9155(4) 0.6346(4) 0.0652(8) Uani 1 1 d . . . . .
C5 C 0.4643(2) 0.8990(4) 0.4658(3) 0.0636(7) Uani 1 1 d . . . . .
H5 H 0.462838 1.029116 0.522758 0.076 Uiso 1 1 calc R U . . .
C7 C 0.5455(2) 0.6557(6) 0.2922(4) 0.0792(9) Uani 1 1 d . . . . .
H7 H 0.599185 0.627840 0.233094 0.095 Uiso 1 1 calc R U . . .
C6 C 0.5420(2) 0.8498(5) 0.3780(4) 0.0759(9) Uani 1 1 d . . . . .
H6 H 0.593531 0.948203 0.375436 0.091 Uiso 1 1 calc R U . . .
C8 C 0.4714(2) 0.5041(5) 0.2930(4) 0.0762(9) Uani 1 1 d . . . . .
H8 H 0.474001 0.373735 0.236408 0.091 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
N1 H1 0.8600 . ?
N1 C9 1.377(4) . ?
N1 C1 1.348(4) . ?
C2 C4 1.433(4) . ?
C2 C1 1.375(3) . ?
C2 C3 1.422(4) . ?
N2 C3 1.148(4) . ?
C4 C9 1.406(3) . ?
C4 C5 1.393(4) . ?
C9 C8 1.389(4) . ?
C1 H1A 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.368(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.392(5) . ?
C7 C8 1.376(5) . ?
C6 H6 0.9300 . ?
C8 H8 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
C9 N1 H1 124.9 . . ?
C1 N1 H1 124.9 . . ?
C1 N1 C9 110.2(2) . . ?
C1 C2 C4 107.5(2) . . ?
C1 C2 C3 126.1(3) . . ?
C3 C2 C4 126.3(2) . . ?
C9 C4 C2 106.0(2) . . ?
C5 C4 C2 134.8(2) . . ?
C5 C4 C9 119.2(2) . . ?
N1 C9 C4 107.5(2) . . ?
N1 C9 C8 130.4(3) . . ?
C8 C9 C4 122.2(3) . . ?
N1 C1 C2 108.9(2) . . ?
N1 C1 H1A 125.6 . . ?
C2 C1 H1A 125.6 . . ?
N2 C3 C2 177.1(3) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.7(3) . . ?
C6 C5 H5 120.7 . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C8 C7 C6 121.5(3) . . ?
C5 C6 C7 121.5(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C9 C8 H8 121.5 . . ?
C7 C8 C9 117.1(3) . . ?
C7 C8 H8 121.5 . . ?

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
N1 C9 C8 C7 178.7(3) . . . . ?
C2 C4 C9 N1 -0.2(3) . . . . ?
C2 C4 C9 C8 178.9(3) . . . . ?
C2 C4 C5 C6 -178.5(3) . . . . ?
C4 C2 C1 N1 0.3(3) . . . . ?
C4 C9 C8 C7 -0.1(5) . . . . ?
C4 C5 C6 C7 -0.1(5) . . . . ?
C9 N1 C1 C2 -0.4(4) . . . . ?
C9 C4 C5 C6 0.6(4) . . . . ?
C1 N1 C9 C4 0.3(3) . . . . ?
C1 N1 C9 C8 -178.6(3) . . . . ?
C1 C2 C4 C9 -0.1(3) . . . . ?
C1 C2 C4 C5 179.1(3) . . . . ?
C3 C2 C4 C9 -176.5(3) . . . . ?
C3 C2 C4 C5 2.7(5) . . . . ?
C3 C2 C1 N1 176.7(3) . . . . ?
C5 C4 C9 N1 -179.5(3) . . . . ?
C5 C4 C9 C8 -0.5(4) . . . . ?
C6 C7 C8 C9 0.6(5) . . . . ?
C8 C7 C6 C5 -0.5(5) . . . . ?

_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder'
_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 1.326
_oxdiff_exptl_absorpt_empirical_full_min 0.737
