# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_exp_513
_database_code_depnum_ccdc_archive 'CCDC 2262732'
loop_
_audit_author_name
_audit_author_address
'Gaurav K. Rastogi'
;Gauhati University
India
;
_audit_update_record             
;
2023-05-13 deposited with the CCDC.	2023-07-11 downloaded from the CCDC.
;
_audit_creation_date             2022-09-21
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        orthorhombic
_chemical_formula_moiety         'C5 H7 N3'
_chemical_formula_sum            'C5 H7 N3'
_chemical_formula_weight         109.14
_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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   21.861(6)
_cell_length_b                   6.7837(16)
_cell_length_c                   7.501(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1112.4(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    467
_cell_measurement_temperature    100
_cell_measurement_theta_max      20.3510
_cell_measurement_theta_min      3.1260
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9653
_exptl_absorpt_correction_T_min  0.8654
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'Bruker APEX-II CCD'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3318
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.988
_diffrn_reflns_theta_max         24.988
_diffrn_reflns_theta_min         3.144
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                548
_reflns_number_total             975
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    ?
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.008(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     75
_refine_ls_number_reflns         975
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1356
_refine_ls_R_factor_gt           0.0835
_refine_ls_restrained_S_all      1.113
_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)+(0.0834P)²+0.5343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2080
_refine_ls_wR_factor_ref         0.2484
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
N3 N 0.52787(14) 0.8147(5) 0.7157(5) 0.0795(13) Uani 1 1 d . . . . .
N2 N 0.60960(18) 0.6134(6) 0.6110(5) 0.0869(13) Uani 1 1 d . . . . .
N1 N 0.62180(19) 0.4180(7) 0.5950(6) 0.1004(15) Uani 1 1 d . . . . .
H1 H 0.655642 0.366395 0.551884 0.120 Uiso 1 1 calc R . . . .
C5 C 0.5533(2) 0.6353(6) 0.6824(5) 0.0704(12) Uani 1 1 d . . . . .
C4 C 0.52873(17) 0.4488(5) 0.7139(5) 0.0667(12) Uani 1 1 d . . . . .
C3 C 0.5746(2) 0.3195(7) 0.6547(6) 0.0889(15) Uani 1 1 d . . . . .
H3 H 0.571740 0.179757 0.657590 0.107 Uiso 1 1 calc R . . . .
C6 C 0.6541(3) 0.7604(9) 0.5575(8) 0.121(2) Uani 1 1 d . . . . .
H6A H 0.632475 0.880809 0.517707 0.146 Uiso 1 1 calc R . . . .
H6B H 0.678132 0.709554 0.455501 0.146 Uiso 1 1 calc R . . . .
C1 C 0.6958(3) 0.8110(11) 0.7034(11) 0.169(3) Uani 1 1 d . . . . .
H1A H 0.728854 0.894414 0.657782 0.253 Uiso 1 1 calc GR . . . .
H1B H 0.713106 0.690001 0.753885 0.253 Uiso 1 1 calc GR . . . .
H1C H 0.673241 0.882282 0.796086 0.253 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
N3 N3 1.323(6) 3_656 ?
N3 C5 1.362(5) . ?
N2 N1 1.358(5) . ?
N2 C5 1.350(5) . ?
N2 C6 1.450(6) . ?
N1 H1 0.8800 . ?
N1 C3 1.308(5) . ?
C5 C4 1.395(5) . ?
C4 C4 1.368(7) 3_656 ?
C4 C3 1.404(5) . ?
C3 H3 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C1 1.464(7) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 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
N3 N3 C5 116.6(2) 3_656 . ?
N1 N2 C6 121.0(4) . . ?
C5 N2 N1 108.7(4) . . ?
C5 N2 C6 130.2(4) . . ?
N2 N1 H1 125.9 . . ?
C3 N1 N2 108.3(4) . . ?
C3 N1 H1 125.9 . . ?
N3 C5 C4 128.5(4) . . ?
N2 C5 N3 122.9(4) . . ?
N2 C5 C4 108.6(3) . . ?
C5 C4 C3 103.8(4) . . ?
C4 C4 C5 114.9(2) 3_656 . ?
C4 C4 C3 141.3(3) 3_656 . ?
N1 C3 C4 110.6(4) . . ?
N1 C3 H3 124.7 . . ?
C4 C3 H3 124.7 . . ?
N2 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
N2 C6 C1 111.8(5) . . ?
H6A C6 H6B 107.9 . . ?
C1 C6 H6A 109.3 . . ?
C1 C6 H6B 109.3 . . ?
C6 C1 H1A 109.5 . . ?
C6 C1 H1B 109.5 . . ?
C6 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
N3 N3 C5 N2 179.3(4) 3_656 . . . ?
N3 N3 C5 C4 -1.2(7) 3_656 . . . ?
N3 C5 C4 C4 0.7(7) . . . 3_656 ?
N3 C5 C4 C3 -179.9(4) . . . . ?
N2 N1 C3 C4 -0.2(5) . . . . ?
N2 C5 C4 C4 -179.7(4) . . . 3_656 ?
N2 C5 C4 C3 -0.3(4) . . . . ?
N1 N2 C5 N3 179.8(4) . . . . ?
N1 N2 C5 C4 0.2(5) . . . . ?
N1 N2 C6 C1 -88.6(6) . . . . ?
C5 N2 N1 C3 0.0(5) . . . . ?
C5 N2 C6 C1 90.3(7) . . . . ?
C5 C4 C3 N1 0.3(5) . . . . ?
C4 C4 C3 N1 179.5(6) 3_656 . . . ?
C6 N2 N1 C3 179.1(4) . . . . ?
C6 N2 C5 N3 0.8(7) . . . . ?
C6 N2 C5 C4 -178.8(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
