# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_skd-f-kp-137smiso-r_auto
_database_code_depnum_ccdc_archive 'CCDC 2283220'
loop_
_audit_author_name
_audit_author_address
'Koustav Pal'
;IISER Kolkata
India
;
_audit_update_record             
;
2023-07-20 deposited with the CCDC.	2024-02-29 downloaded from the CCDC.
;
_audit_creation_date             2023-06-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.154(C10 H9 N3)'
_chemical_formula_sum            'C1.54 H1.38 N0.46'
_chemical_formula_weight         26.34
_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      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                   6.3402(3)
_cell_length_b                   7.4033(3)
_cell_length_c                   10.8259(4)
_cell_angle_alpha                102.832(4)
_cell_angle_beta                 92.959(3)
_cell_angle_gamma                114.223(4)
_cell_volume                     445.98(4)
_cell_formula_units_Z            13
_cell_measurement_reflns_used    4020
_cell_measurement_temperature    107(4)
_cell_measurement_theta_max      67.6350
_cell_measurement_theta_min      4.2110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             180
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7820
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.100
_diffrn_reflns_theta_min         4.243
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      107(4)
_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 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     28.00 105.00   0.50    0.25    --   96.35 -77.00 150.00  154
  2  ω     28.00 105.00   0.50    0.25    --   96.35 -77.00  30.00  154
  3  ω    -29.00  31.00   0.50    0.20    --   40.58 -25.00   0.00  120
  4  ω    -26.00  57.00   0.50    0.20    --   40.58 -50.00  30.00  166
  5  ω    -35.00  24.00   0.50    0.20    --   40.58 -12.00 150.00  118
  6  ω     28.00  68.00   0.50    0.25    --   96.35 -59.00 150.00   80
  7  ω     29.00  83.00   0.50    0.25    --   96.35 -68.00  90.00  108
  8  ω     28.00  68.00   0.50    0.25    --   96.35 -59.00 -30.00   80
  9  ω     28.00  68.00   0.50    0.25    --   96.35 -59.00 -60.00   80
 10  ω     29.00  83.00   0.50    0.25    --   96.35 -68.00 -90.00  108
 11  ω     30.00  57.00   0.50    0.25    --   96.35 -50.00 -90.00   54
 12  ω     28.00  68.00   0.50    0.25    --   96.35 -59.00-180.00   80
 13  ω     26.00 127.00   0.50    0.25    --   96.35 -87.00 -90.00  202
 14  ω     44.00 127.00   0.50    0.25    --   96.35-145.00-120.00  166
 15  ω     39.00 119.00   0.50    0.25    --   96.35-135.00 -64.00  160
 16  ω     33.00 110.00   0.50    0.25    --   96.35-117.00 -90.00  154
 17  ω     33.00 110.00   0.50    0.25    --   96.35-117.00   0.00  154
 18  ω     39.00 119.00   0.50    0.25    --   96.35-134.00 114.00  160
 19  ω     39.00  96.00   0.50    0.20    --   40.58-134.00 114.00  114
 20  ω     81.00 167.00   0.50    0.25    --   96.35  25.00 -60.00  172
 21  ω     77.00 163.00   0.50    0.25    --   96.35  50.00   0.00  172
 22  ω     70.00 165.00   0.50    0.25    --   96.35  77.00-120.00  190
 23  ω     70.00 165.00   0.50    0.25    --   96.35  77.00 -60.00  190
 24  ω     83.00 164.00   0.50    0.25    --   96.35  33.00-120.00  162
 25  ω     72.00 164.00   0.50    0.25    --   96.35  68.00  60.00  184
 26  ω     70.00 165.00   0.50    0.25    --   96.35  77.00 150.00  190
 27  ω     83.00 164.00   0.50    0.25    --   96.35  33.00 120.00  162
 28  ω     81.00 167.00   0.50    0.25    --   96.35  25.00  60.00  172
 29  ω     81.00 167.00   0.50    0.25    --   96.35  25.00-180.00  172
 30  ω     99.00 160.00   0.50    0.25    --   96.35 117.00-150.00  122
 31  ω     81.00 165.00   0.50    0.25    --   96.35 145.00-120.00  168
 32  ω     89.00 162.00   0.50    0.25    --   96.35 134.00-179.00  146
 33  ω     88.00 164.00   0.50    0.25    --   96.35 135.00   0.00  152
 34  ω     18.00 108.00   0.50    0.20    --   40.58  64.00 -90.00  180
 35  ω     14.00 109.00   0.50    0.20    --   40.58  77.00-180.00  190
 36  ω     14.00 109.00   0.50    0.20    --   40.58  77.00 120.00  190
 37  ω    -94.00 -18.00   0.50    0.20    --  -40.58 135.00   0.00  152
 38  ω    -93.00 -17.00   0.50    0.20    --  -40.58 134.00-179.00  152
 39  ω    -93.00 -17.00   0.50    0.25    --  -82.50 134.00-179.00  152
 40  ω    -57.00 -16.00   0.50    0.25    --  -82.50  50.00-120.00   82
 41  ω    -47.00 -15.00   0.50    0.25    --  -82.50  42.00-180.00   64
 42  ω    -47.00 -15.00   0.50    0.25    --  -82.50  42.00 -30.00   64
 43  ω    -47.00 -15.00   0.50    0.25    --  -82.50  42.00   0.00   64
 44  ω    -47.00 -15.00   0.50    0.25    --  -82.50  42.00  60.00   64
 45  ω    -43.00  26.00   0.50    0.20    --  -40.58  38.00   0.00  138
 46  ω    -43.00  26.00   0.50    0.20    --  -40.58  38.00  30.00  138
 47  ω    -24.00  35.00   0.50    0.20    --  -40.58  12.00 -60.00  118
 48  ω    -24.00  35.00   0.50    0.20    --  -40.58  12.00-150.00  118
 49  ω    -24.00  35.00   0.50    0.20    --  -40.58  12.00-120.00  118
 50  ω   -108.00 -17.00   0.50    0.20    --  -40.58 -64.00 -30.00  182
 51  ω   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00  30.00  190
 52  ω   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00  60.00  190
 53  ω   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00  90.00  190
 54  ω   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00-180.00  190
 55  ω   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00-120.00  190
 56  ω   -108.00 -17.00   0.50    0.20    --  -40.58 -64.00 -90.00  182
 57  ω   -151.00 -55.00   0.50    0.25    --  -82.50 -77.00  30.00  192
 58  ω   -151.00 -55.00   0.50    0.25    --  -82.50 -77.00  90.00  192
 59  ω   -151.00 -61.00   0.50    0.25    --  -82.50 -59.00 120.00  180
 60  ω   -150.00 -69.00   0.50    0.25    --  -82.50 -33.00 150.00  162
 61  ω   -151.00 -55.00   0.50    0.25    --  -82.50 -77.00   0.00  192
 62  ω   -151.00 -55.00   0.50    0.25    --  -82.50 -77.00-150.00  192
 63  ω   -151.00 -55.00   0.50    0.25    --  -82.50 -77.00 -90.00  192
 64  ω   -150.00 -66.00   0.50    0.25    --  -82.50-135.00 -64.00  168
 65  ω   -148.00 -67.00   0.50    0.25    --  -82.50-134.00 114.00  162
;
_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      -0.0922119000
_diffrn_orient_matrix_UB_12      -0.0327659000
_diffrn_orient_matrix_UB_13      0.1259702000
_diffrn_orient_matrix_UB_21      -0.2311253000
_diffrn_orient_matrix_UB_22      -0.1765738000
_diffrn_orient_matrix_UB_23      -0.0774229000
_diffrn_orient_matrix_UB_31      0.1046298000
_diffrn_orient_matrix_UB_32      -0.1543211000
_diffrn_orient_matrix_UB_33      0.0012358000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1430
_reflns_number_total             1604
_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 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1604
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.085
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1339
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C005(H005), C006(H006), C007(H007), C009(H009), C00B(H00B), C00C(H00C)
2.b Idealised Me refined as rotating group:
 C00D(H00A,H00D,H00E)
;
_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
N001 N 0.63153(16) 0.25212(13) 0.44402(9) 0.0253(3) Uani 1 1 d . . . . .
N002 N 0.43443(15) 0.23640(13) 0.47188(9) 0.0249(3) Uani 1 1 d . . . . .
N003 N 0.93695(16) 0.22814(14) 0.04899(8) 0.0347(3) Uani 1 1 d . . . . .
C004 C 0.41890(18) 0.25345(15) 0.60448(10) 0.0235(3) Uani 1 1 d . . . . .
C005 C 0.60199(19) 0.28482(15) 0.69707(10) 0.0255(3) Uani 1 1 d . . . . .
H005 H 0.747662 0.295407 0.672870 0.031 Uiso 1 1 calc R U . . .
C006 C 0.17484(19) 0.25288(16) 0.76738(11) 0.0273(3) Uani 1 1 d . . . . .
H006 H 0.029500 0.242674 0.791917 0.033 Uiso 1 1 calc R U . . .
C007 C 0.85366(19) 0.25061(15) 0.28110(10) 0.0270(3) Uani 1 1 d . . . . .
H007 H 0.973551 0.271814 0.346624 0.032 Uiso 1 1 calc R U . . .
C008 C 0.64396(19) 0.23391(15) 0.31167(10) 0.0241(3) Uani 1 1 d . . . . .
C009 C 0.57035(18) 0.30035(15) 0.82380(10) 0.0267(3) Uani 1 1 d . . . . .
H009 H 0.694616 0.322463 0.886855 0.032 Uiso 1 1 calc R U . . .
C00A C 0.89917(18) 0.23707(16) 0.15229(10) 0.0278(3) Uani 1 1 d . . . . .
C00B C 0.35566(19) 0.28352(15) 0.85899(10) 0.0267(3) Uani 1 1 d . . . . .
H00B H 0.333532 0.293102 0.945919 0.032 Uiso 1 1 calc R U . . .
C00C C 0.20472(18) 0.23700(15) 0.64004(10) 0.0258(3) Uani 1 1 d . . . . .
H00C H 0.079987 0.215046 0.577354 0.031 Uiso 1 1 calc R U . . .
C00D C 0.44150(18) 0.20136(16) 0.21870(10) 0.0277(3) Uani 1 1 d . . . . .
H00A H 0.301055 0.084635 0.227189 0.041 Uiso 1 1 calc R U . . .
H00D H 0.475717 0.172778 0.131125 0.041 Uiso 1 1 calc R U . . .
H00E H 0.414674 0.325263 0.236675 0.041 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
N001 N002 1.2654(13) . ?
N001 C008 1.4185(13) . ?
N002 C004 1.4251(15) . ?
N003 C00A 1.1489(13) . ?
C004 C005 1.4005(16) . ?
C004 C00C 1.3951(14) . ?
C005 H005 0.9500 . ?
C005 C009 1.3832(14) . ?
C006 H006 0.9500 . ?
C006 C00B 1.3851(16) . ?
C006 C00C 1.3868(14) . ?
C007 H007 0.9500 . ?
C007 C008 1.3495(15) . ?
C007 C00A 1.4287(14) . ?
C008 C00D 1.4913(16) . ?
C009 H009 0.9500 . ?
C009 C00B 1.3960(15) . ?
C00B H00B 0.9500 . ?
C00C H00C 0.9500 . ?
C00D H00A 0.9800 . ?
C00D H00D 0.9800 . ?
C00D H00E 0.9800 . ?

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
N002 N001 C008 113.02(10) . . ?
N001 N002 C004 113.67(10) . . ?
C005 C004 N002 124.14(10) . . ?
C00C C004 N002 115.85(10) . . ?
C00C C004 C005 120.00(10) . . ?
C004 C005 H005 120.1 . . ?
C009 C005 C004 119.89(10) . . ?
C009 C005 H005 120.1 . . ?
C00B C006 H006 119.8 . . ?
C00B C006 C00C 120.39(10) . . ?
C00C C006 H006 119.8 . . ?
C008 C007 H007 119.3 . . ?
C008 C007 C00A 121.39(10) . . ?
C00A C007 H007 119.3 . . ?
N001 C008 C00D 121.74(9) . . ?
C007 C008 N001 113.42(10) . . ?
C007 C008 C00D 124.84(10) . . ?
C005 C009 H009 120.0 . . ?
C005 C009 C00B 119.95(10) . . ?
C00B C009 H009 120.0 . . ?
N003 C00A C007 179.36(11) . . ?
C006 C00B C009 120.12(10) . . ?
C006 C00B H00B 119.9 . . ?
C009 C00B H00B 119.9 . . ?
C004 C00C H00C 120.2 . . ?
C006 C00C C004 119.65(10) . . ?
C006 C00C H00C 120.2 . . ?
C008 C00D H00A 109.5 . . ?
C008 C00D H00D 109.5 . . ?
C008 C00D H00E 109.5 . . ?
H00A C00D H00D 109.5 . . ?
H00A C00D H00E 109.5 . . ?
H00D C00D H00E 109.5 . . ?

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
N001 N002 C004 C005 0.05(17) . . . . ?
N001 N002 C004 C00C -179.97(8) . . . . ?
N002 N001 C008 C007 179.97(8) . . . . ?
N002 N001 C008 C00D 0.46(15) . . . . ?
N002 C004 C005 C009 179.69(8) . . . . ?
N002 C004 C00C C006 -179.67(8) . . . . ?
C004 C005 C009 C00B 0.38(16) . . . . ?
C005 C004 C00C C006 0.31(16) . . . . ?
C005 C009 C00B C006 -0.50(16) . . . . ?
C008 N001 N002 C004 179.73(7) . . . . ?
C00A C007 C008 N001 -179.74(8) . . . . ?
C00A C007 C008 C00D -0.25(17) . . . . ?
C00B C006 C00C C004 -0.43(16) . . . . ?
C00C C004 C005 C009 -0.29(16) . . . . ?
C00C C006 C00B C009 0.53(16) . . . . ?

_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 1.966
_oxdiff_exptl_absorpt_empirical_full_min 0.837
