# Supplementary Information (SI) for Chemical Science.
# 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_deabcn2
_database_code_depnum_ccdc_archive 'CCDC 2017383'
loop_
_audit_author_name
_audit_author_address
'Mrinal Mandal and Prof. Prasun K. Mandal'
;IISER Kolkata
India
;
_audit_update_record             
;
2022-10-01 deposited with the CCDC.	2024-11-17 downloaded from the CCDC.
;
_audit_creation_date             2020-04-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H15 N3'
_chemical_formula_sum            'C14 H15 N3'
_chemical_formula_weight         225.29
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.7161(6)
_cell_length_b                   9.2511(7)
_cell_length_c                   9.8844(7)
_cell_angle_alpha                63.309(8)
_cell_angle_beta                 64.432(7)
_cell_angle_gamma                72.772(7)
_cell_volume                     637.16(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5436
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      65.7690
_cell_measurement_theta_min      5.3460
_exptl_absorpt_coefficient_mu    0.561
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9819
_diffrn_reflns_theta_full        66.25
_diffrn_reflns_theta_max         66.25
_diffrn_reflns_theta_min         5.35
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -50.00   64.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311  -57.0000   30.0000 114

#__ type_ start__ end____ width___ exp.time_
  2 omega   55.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311 -178.0000   60.0000 66

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00   64.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311  -57.0000  120.0000 114

#__ type_ start__ end____ width___ exp.time_
  4 omega  -12.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311   57.0000 -120.0000 114

#__ type_ start__ end____ width___ exp.time_
  5 omega  -12.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311   57.0000 -180.0000 114

#__ type_ start__ end____ width___ exp.time_
  6 omega   -4.00  109.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656  -94.0000 -150.0000 113

#__ type_ start__ end____ width___ exp.time_
  7 omega  100.00  153.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656  111.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
  8 omega   30.00  144.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   61.0000  -60.0000 114

#__ type_ start__ end____ width___ exp.time_
  9 omega  100.00  153.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656  111.0000 -120.0000 53

#__ type_ start__ end____ width___ exp.time_
 10 omega   30.00  144.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   61.0000 -120.0000 114

#__ type_ start__ end____ width___ exp.time_
 11 omega   30.00  144.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   61.0000   60.0000 114

#__ type_ start__ end____ width___ exp.time_
 12 omega   57.00  150.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656  178.0000 -120.0000 93

#__ type_ start__ end____ width___ exp.time_
 13 omega   30.00  144.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   61.0000 -180.0000 114

#__ type_ start__ end____ width___ exp.time_
 14 omega   30.00  144.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   61.0000    0.0000 114

#__ type_ start__ end____ width___ exp.time_
 15 omega  100.00  153.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656  111.0000  150.0000 53

#__ type_ start__ end____ width___ exp.time_
 16 omega  101.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000  -30.0000 77

#__ type_ start__ end____ width___ exp.time_
 17 omega   29.00  145.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -65.0000 -180.0000 116

#__ type_ start__ end____ width___ exp.time_
 18 omega   21.00  113.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000  150.0000 92

#__ type_ start__ end____ width___ exp.time_
 19 omega   36.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   32.0000   30.0000 142

#__ type_ start__ end____ width___ exp.time_
 20 omega   69.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   54.0000   60.0000 109

#__ type_ start__ end____ width___ exp.time_
 21 omega   71.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   65.0000   90.0000 107

#__ type_ start__ end____ width___ exp.time_
 22 omega   21.00  113.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000  -60.0000 92

#__ type_ start__ end____ width___ exp.time_
 23 omega   21.00  113.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000   30.0000 92

#__ type_ start__ end____ width___ exp.time_
 24 omega   86.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  138.0000    0.0000 92

#__ type_ start__ end____ width___ exp.time_
 25 omega   19.00  158.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -89.0000  -60.0000 139

#__ type_ start__ end____ width___ exp.time_
 26 omega   23.00  151.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 128

#__ type_ start__ end____ width___ exp.time_
 27 omega  101.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000   90.0000 77

#__ type_ start__ end____ width___ exp.time_
 28 omega   25.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   21.0000  -30.0000 153

#__ type_ start__ end____ width___ exp.time_
 29 omega   31.00  147.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -54.0000    0.0000 116

#__ type_ start__ end____ width___ exp.time_
 30 omega   21.00  113.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000 -180.0000 92

#__ type_ start__ end____ width___ exp.time_
 31 omega   29.00  145.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -65.0000    0.0000 116

#__ type_ start__ end____ width___ exp.time_
 32 omega   69.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   54.0000    0.0000 109

#__ type_ start__ end____ width___ exp.time_
 33 omega  101.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000  -60.0000 77

#__ type_ start__ end____ width___ exp.time_
 34 omega  -17.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311   77.0000   60.0000 128

#__ type_ start__ end____ width___ exp.time_
 35 omega  -50.00   64.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311  -57.0000  -60.0000 114

#__ type_ start__ end____ width___ exp.time_
 36 omega  -17.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311   77.0000  120.0000 128

#__ type_ start__ end____ width___ exp.time_
 37 omega  -12.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311   57.0000 -150.0000 114

#__ type_ start__ end____ width___ exp.time_
 38 omega  -12.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       26.3311   57.0000  -30.0000 114

#__ type_ start__ end____ width___ exp.time_
 39 omega  100.00  153.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656  111.0000   30.0000 53

#__ type_ start__ end____ width___ exp.time_
 40 omega   24.00  152.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   77.0000  -90.0000 128

#__ type_ start__ end____ width___ exp.time_
 41 omega   24.00  152.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   77.0000   60.0000 128

#__ type_ start__ end____ width___ exp.time_
 42 omega   24.00  152.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   77.0000 -150.0000 128

#__ type_ start__ end____ width___ exp.time_
 43 omega   25.00  152.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   76.0000  -13.8545 127

#__ type_ start__ end____ width___ exp.time_
 44 omega   24.00  152.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   77.0000  120.0000 128

#__ type_ start__ end____ width___ exp.time_
 45 omega   30.00  144.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   61.0000  120.0000 114

#__ type_ start__ end____ width___ exp.time_
 46 omega   24.00  152.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   77.0000   30.0000 128

#__ type_ start__ end____ width___ exp.time_
 47 omega   24.00  152.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656   77.0000  150.0000 128

#__ type_ start__ end____ width___ exp.time_
 48 omega  100.00  153.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -       67.1656  111.0000   90.0000 53

#__ type_ start__ end____ width___ exp.time_
 49 omega   65.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 113

#__ type_ start__ end____ width___ exp.time_
 50 omega   65.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 113

#__ type_ start__ end____ width___ exp.time_
 51 omega   65.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 113

#__ type_ start__ end____ width___ exp.time_
 52 omega   65.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 113

#__ type_ start__ end____ width___ exp.time_
 53 omega   65.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 113

#__ type_ start__ end____ width___ exp.time_
 54 omega   65.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 113

#__ type_ start__ end____ width___ exp.time_
 55 omega   65.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 113

#__ type_ start__ end____ width___ exp.time_
 56 omega   65.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 113

#__ type_ start__ end____ width___ exp.time_
 57 omega   58.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   43.0000 -120.0000 120

#__ type_ start__ end____ width___ exp.time_
 58 omega   58.00  178.00   1.0000    5.0100
omega____ theta____ kappa____ phi______ frames
    -      108.0000   43.0000 -180.0000 120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1757
_reflns_number_total             2213
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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         0.385
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.022(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0782
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1021P)²+0.3208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2270
_refine_ls_wR_factor_ref         0.2367
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C7(H7), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1 N 0.2423(4) 0.8107(4) 0.7100(4) 0.0793(9) Uani 1 d . . .
C6 C 0.5793(4) 0.6948(3) 0.8863(3) 0.0560(7) Uani 1 d . . .
C8 C 0.8426(4) 0.4978(3) 0.8038(3) 0.0579(7) Uani 1 d . . .
N2 N 1.1151(4) 0.3286(4) 0.8646(4) 0.0881(9) Uani 1 d . . .
C1 C 0.4916(4) 0.7091(3) 0.7907(3) 0.0583(7) Uani 1 d . . .
H1 H 0.5390 0.6515 0.7222 0.070 Uiso 1 calc . . R
C9 C 0.8116(4) 0.4796(4) 0.6815(4) 0.0652(8) Uani 1 d . . .
N3 N 0.7911(4) 0.4638(4) 0.5831(4) 0.0949(10) Uani 1 d . . .
C3 C 0.2729(4) 0.8985(4) 0.8946(4) 0.0697(9) Uani 1 d . . .
H3 H 0.1721 0.9702 0.8961 0.084 Uiso 1 calc . . R
C2 C 0.3347(4) 0.8074(3) 0.7950(3) 0.0612(8) Uani 1 d . . .
C10 C 0.9950(4) 0.4033(4) 0.8360(4) 0.0677(8) Uani 1 d . . .
C7 C 0.7401(4) 0.5917(3) 0.8892(3) 0.0606(8) Uani 1 d . . .
H7 H 0.7799 0.5899 0.9635 0.073 Uiso 1 calc . . R
C5 C 0.5099(4) 0.7819(4) 0.9883(4) 0.0682(8) Uani 1 d . . .
H5 H 0.5654 0.7714 1.0548 0.082 Uiso 1 calc . . R
C4 C 0.3587(4) 0.8832(4) 0.9891(4) 0.0740(9) Uani 1 d . . .
H4 H 0.3133 0.9430 1.0555 0.089 Uiso 1 calc . . R
C11 C 0.3095(5) 0.7189(5) 0.6045(4) 0.0785(10) Uani 1 d . . .
H11A H 0.2143 0.7035 0.5882 0.094 Uiso 1 calc . . R
H11B H 0.3611 0.6118 0.6592 0.094 Uiso 1 calc . . R
C13 C 0.0774(5) 0.9159(5) 0.7141(5) 0.0949(12) Uani 1 d . . .
H13A H 0.0122 0.9119 0.8236 0.114 Uiso 1 calc . . R
H13B H 0.0121 0.8742 0.6840 0.114 Uiso 1 calc . . R
C12 C 0.4388(6) 0.7953(6) 0.4434(5) 0.1094(14) Uani 1 d . . .
H12A H 0.3847 0.8936 0.3810 0.164 Uiso 1 calc . . GR
H12B H 0.4862 0.7208 0.3879 0.164 Uiso 1 calc . . GR
H12C H 0.5287 0.8208 0.4574 0.164 Uiso 1 calc . . GR
C14 C 0.0996(7) 1.0875(6) 0.6039(6) 0.1193(16) Uani 1 d . . .
H14A H 0.1674 1.0919 0.4959 0.179 Uiso 1 calc . . GR
H14B H 0.1565 1.1321 0.6381 0.179 Uiso 1 calc . . GR
H14C H -0.0106 1.1499 0.6062 0.179 Uiso 1 calc . . GR


_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 C2 1.379(4) . ?
N1 C11 1.458(4) . ?
N1 C13 1.474(4) . ?
C6 C1 1.395(4) . ?
C6 C7 1.447(4) . ?
C6 C5 1.395(4) . ?
C8 C9 1.433(4) . ?
C8 C10 1.435(4) . ?
C8 C7 1.347(4) . ?
N2 C10 1.142(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.395(4) . ?
C9 N3 1.137(4) . ?
C3 H3 0.9300 . ?
C3 C2 1.409(4) . ?
C3 C4 1.369(4) . ?
C7 H7 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.372(4) . ?
C4 H4 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.489(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.480(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C2 N1 C11 121.3(3) . . ?
C2 N1 C13 121.1(3) . . ?
C11 N1 C13 117.6(3) . . ?
C1 C6 C7 124.0(2) . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 C7 116.5(3) . . ?
C9 C8 C10 115.1(2) . . ?
C7 C8 C9 125.4(3) . . ?
C7 C8 C10 119.5(3) . . ?
C6 C1 H1 119.1 . . ?
C6 C1 C2 121.8(3) . . ?
C2 C1 H1 119.1 . . ?
N3 C9 C8 178.4(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C4 C3 C2 121.2(3) . . ?
N1 C2 C1 121.4(3) . . ?
N1 C2 C3 121.8(3) . . ?
C1 C2 C3 116.8(3) . . ?
N2 C10 C8 178.6(3) . . ?
C6 C7 H7 114.2 . . ?
C8 C7 C6 131.6(3) . . ?
C8 C7 H7 114.2 . . ?
C6 C5 H5 120.5 . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 H5 120.5 . . ?
C3 C4 C5 121.6(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
N1 C11 H11A 108.5 . . ?
N1 C11 H11B 108.5 . . ?
N1 C11 C12 115.2(3) . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
N1 C13 H13A 109.1 . . ?
N1 C13 H13B 109.1 . . ?
N1 C13 C14 112.5(4) . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_test5_a
_database_code_depnum_ccdc_archive 'CCDC 2042111'
loop_
_audit_author_name
_audit_author_address
'Mrinal Mandal and Prof. Prasun K. Mandal'
;IISER Kolkata
India
;
_audit_update_record             
;
2022-10-01 deposited with the CCDC.	2024-11-17 downloaded from the CCDC.
;
_audit_creation_date             2020-10-31
_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 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_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                   15.292(4)
_cell_length_b                   10.450(3)
_cell_length_c                   6.872(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.614(10)
_cell_angle_gamma                90
_cell_volume                     1088.5(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2119
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      26.76
_cell_measurement_theta_min      3.32
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4157
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1464 before and 0.0925 after correction.
The Ratio of minimum to maximum transmission is 0.5576.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1244
_diffrn_reflns_av_unetI/netI     0.0987
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8292
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.367
_diffrn_ambient_temperature      301.05
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1260
_reflns_number_total             1908
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.027(10)
_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   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1908
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1509
_refine_ls_R_factor_gt           0.1058
_refine_ls_restrained_S_all      1.126
_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)+(0.0961P)²+1.4564P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2431
_refine_ls_wR_factor_ref         0.2667
_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:
 C003(H003), C005(H005), C009(H009), C00C(H00C), C00D(H00D)
2.b Idealised Me refined as rotating group:
 C00E(H00A,H00B,H00E), C00F(H00F,H00G,H00H)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.6332(3) 0.0121(4) 0.2874(6) 0.0562(12) Uani 1 1 d . . . . .
C002 C 0.8350(3) 0.2086(4) 0.3462(6) 0.0346(10) Uani 1 1 d . . . . .
C003 C 0.8656(3) 0.3398(4) 0.3559(6) 0.0385(11) Uani 1 1 d . . . . .
H003 H 0.926612 0.348716 0.373947 0.046 Uiso 1 1 calc R . . . .
C004 C 0.8212(3) 0.4506(4) 0.3434(6) 0.0373(11) Uani 1 1 d . . . . .
C005 C 0.7463(3) 0.1735(4) 0.3227(6) 0.0376(11) Uani 1 1 d . . . . .
H005 H 0.703234 0.236884 0.314119 0.045 Uiso 1 1 calc R . . . .
C006 C 0.7277(3) 0.4665(4) 0.3139(7) 0.0446(12) Uani 1 1 d . . . . .
C007 C 0.7205(3) 0.0445(4) 0.3117(6) 0.0431(11) Uani 1 1 d . . . . .
N008 N 0.6532(3) 0.4830(5) 0.2922(8) 0.0729(15) Uani 1 1 d . . . . .
C009 C 0.9000(3) 0.1144(5) 0.3609(6) 0.0470(12) Uani 1 1 d . . . . .
H009 H 0.959355 0.136742 0.375537 0.056 Uiso 1 1 calc R . . . .
N00A N 0.9109(3) 0.6599(4) 0.3782(8) 0.0720(14) Uani 1 1 d . . . . .
C00B C 0.8704(3) 0.5685(5) 0.3608(7) 0.0483(12) Uani 1 1 d . . . . .
C00C C 0.7873(4) -0.0465(5) 0.3296(7) 0.0522(13) Uani 1 1 d . . . . .
H00C H 0.772217 -0.132735 0.325233 0.063 Uiso 1 1 calc R . . . .
C00D C 0.8748(3) -0.0132(5) 0.3535(7) 0.0520(13) Uani 1 1 d . . . . .
H00D H 0.917699 -0.076792 0.364808 0.062 Uiso 1 1 calc R . . . .
C00E C 0.5654(3) 0.1101(6) 0.2684(10) 0.0781(19) Uani 1 1 d . . . . .
H00A H 0.572789 0.163726 0.382781 0.117 Uiso 1 1 calc GR . . . .
H00B H 0.508341 0.070390 0.255665 0.117 Uiso 1 1 calc GR . . . .
H00E H 0.570282 0.161036 0.154034 0.117 Uiso 1 1 calc GR . . . .
C00F C 0.6056(5) -0.1197(6) 0.2803(10) 0.088(2) Uani 1 1 d . . . . .
H00F H 0.634034 -0.164620 0.184262 0.132 Uiso 1 1 calc GR . . . .
H00G H 0.542742 -0.124039 0.245021 0.132 Uiso 1 1 calc GR . . . .
H00H H 0.621442 -0.158301 0.406760 0.132 Uiso 1 1 calc GR . . . .


_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 C007 1.366(6) . ?
N001 C00E 1.450(7) . ?
N001 C00F 1.440(7) . ?
C002 C003 1.447(6) . ?
C002 C005 1.394(6) . ?
C002 C009 1.393(6) . ?
C003 H003 0.9300 . ?
C003 C004 1.339(6) . ?
C004 C006 1.427(6) . ?
C004 C00B 1.440(6) . ?
C005 H005 0.9300 . ?
C005 C007 1.403(6) . ?
C006 N008 1.142(6) . ?
C007 C00C 1.389(7) . ?
C009 H009 0.9300 . ?
C009 C00D 1.387(7) . ?
N00A C00B 1.136(6) . ?
C00C H00C 0.9300 . ?
C00C C00D 1.371(7) . ?
C00D H00D 0.9300 . ?
C00E H00A 0.9600 . ?
C00E H00B 0.9600 . ?
C00E H00E 0.9600 . ?
C00F H00F 0.9600 . ?
C00F H00G 0.9600 . ?
C00F H00H 0.9600 . ?

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
C007 N001 C00E 120.7(4) . . ?
C007 N001 C00F 121.3(5) . . ?
C00F N001 C00E 118.0(5) . . ?
C005 C002 C003 123.9(4) . . ?
C009 C002 C003 116.3(4) . . ?
C009 C002 C005 119.8(4) . . ?
C002 C003 H003 114.4 . . ?
C004 C003 C002 131.2(4) . . ?
C004 C003 H003 114.4 . . ?
C003 C004 C006 126.8(4) . . ?
C003 C004 C00B 118.6(4) . . ?
C006 C004 C00B 114.5(4) . . ?
C002 C005 H005 119.3 . . ?
C002 C005 C007 121.4(4) . . ?
C007 C005 H005 119.3 . . ?
N008 C006 C004 177.9(5) . . ?
N001 C007 C005 120.5(4) . . ?
N001 C007 C00C 122.4(4) . . ?
C00C C007 C005 117.0(4) . . ?
C002 C009 H009 120.5 . . ?
C00D C009 C002 119.0(4) . . ?
C00D C009 H009 120.5 . . ?
N00A C00B C004 178.1(5) . . ?
C007 C00C H00C 118.9 . . ?
C00D C00C C007 122.1(4) . . ?
C00D C00C H00C 118.9 . . ?
C009 C00D H00D 119.7 . . ?
C00C C00D C009 120.7(4) . . ?
C00C C00D H00D 119.7 . . ?
N001 C00E H00A 109.5 . . ?
N001 C00E H00B 109.5 . . ?
N001 C00E H00E 109.5 . . ?
H00A C00E H00B 109.5 . . ?
H00A C00E H00E 109.5 . . ?
H00B C00E H00E 109.5 . . ?
N001 C00F H00F 109.5 . . ?
N001 C00F H00G 109.5 . . ?
N001 C00F H00H 109.5 . . ?
H00F C00F H00G 109.5 . . ?
H00F C00F H00H 109.5 . . ?
H00G C00F H00H 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
