# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_mo_ncsu_pn51_0m
_database_code_depnum_ccdc_archive 'CCDC 2341280'
loop_
_audit_author_name
_audit_author_address
'Phattananawee Nalaoh'
;The University of Tennessee, Knoxville
United States of America
;
_audit_update_record             
;
2024-03-18 deposited with the CCDC.	2024-05-29 downloaded from the CCDC.
;
_audit_creation_date             2023-07-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H11 N3'
_chemical_formula_sum            'C11 H11 N3'
_chemical_formula_weight         185.23
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.710(3)
_cell_length_b                   3.9545(4)
_cell_length_c                   23.298(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.074(5)
_cell_angle_gamma                90
_cell_volume                     1998.9(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5084
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1251 before and 0.0580 after correction.
The Ratio of minimum to maximum transmission is 0.8774.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 0.00 0.0130
0.00 0.00 -1.00 0.1280
0.00 0.00 1.00 0.0870
0.00 -1.00 1.00 0.2610
0.00 1.00 -1.00 0.2080
1.00 0.00 0.00 0.0400

_exptl_crystal_size_max          0.573
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12063
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.730
_diffrn_reflns_theta_min         2.520
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.41
_diffrn_source_power             0.0705
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1830
_reflns_number_total             2098
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2098
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0547P)²+2.8194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1216
_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, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.39865(6) 0.7000(3) 0.67171(5) 0.0167(3) Uani 1 1 d . . . . .
H1 H 0.4278(9) 0.697(5) 0.6973(8) 0.025 Uiso 1 1 d . U . . .
N2 N 0.58168(7) 0.0475(4) 0.54168(6) 0.0307(4) Uani 1 1 d . . . . .
N3 N 0.54995(6) 0.5861(4) 0.70396(6) 0.0286(3) Uani 1 1 d . . . . .
C1 C 0.33041(7) 1.0017(4) 0.73800(6) 0.0205(3) Uani 1 1 d . . . . .
H1A H 0.366497 1.136269 0.750115 0.031 Uiso 1 1 calc R U . . .
H1B H 0.322251 0.832009 0.767422 0.031 Uiso 1 1 calc R U . . .
H1C H 0.294521 1.150410 0.732860 0.031 Uiso 1 1 calc R U . . .
C2 C 0.34252(6) 0.8292(4) 0.68268(6) 0.0169(3) Uani 1 1 d . . . . .
C3 C 0.39691(7) 0.5517(4) 0.61752(6) 0.0168(3) Uani 1 1 d . . . . .
C4 C 0.44547(7) 0.3940(4) 0.58996(6) 0.0177(3) Uani 1 1 d . . . . .
H4 H 0.434796 0.300624 0.553365 0.021 Uiso 1 1 calc R U . . .
C5 C 0.50629(7) 0.3531(4) 0.60757(6) 0.0182(3) Uani 1 1 d . . . . .
C6 C 0.54831(7) 0.1845(4) 0.57113(7) 0.0220(3) Uani 1 1 d . . . . .
C7 C 0.53118(7) 0.4802(4) 0.66076(7) 0.0210(3) Uani 1 1 d . . . . .
C8 C 0.33637(6) 0.5949(4) 0.59459(6) 0.0165(3) Uani 1 1 d . . . . .
C9 C 0.31359(7) 0.4779(4) 0.53645(6) 0.0199(3) Uani 1 1 d . . . . .
H9A H 0.329372 0.628503 0.506981 0.030 Uiso 1 1 calc R U . . .
H9B H 0.268429 0.481731 0.534535 0.030 Uiso 1 1 calc R U . . .
H9C H 0.328069 0.246953 0.529798 0.030 Uiso 1 1 calc R U . . .
C10 C 0.30267(6) 0.7689(4) 0.63531(6) 0.0168(3) Uani 1 1 d . . . . .
C11 C 0.23623(7) 0.8765(4) 0.62966(7) 0.0211(3) Uani 1 1 d . . . . .
H11A H 0.233352 1.092702 0.609171 0.032 Uiso 1 1 calc R U . . .
H11B H 0.219601 0.902349 0.667957 0.032 Uiso 1 1 calc R U . . .
H11C H 0.212486 0.704550 0.608158 0.032 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 0.85(2) . ?
N1 C2 1.3542(19) . ?
N1 C3 1.3913(19) . ?
N2 C6 1.151(2) . ?
N3 C7 1.151(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.490(2) . ?
C2 C10 1.398(2) . ?
C3 C4 1.401(2) . ?
C3 C8 1.411(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.378(2) . ?
C5 C6 1.433(2) . ?
C5 C7 1.425(2) . ?
C8 C9 1.4982(19) . ?
C8 C10 1.400(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.505(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
C2 N1 H1 121.6(12) . . ?
C2 N1 C3 109.59(12) . . ?
C3 N1 H1 128.5(12) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C2 C1 121.61(13) . . ?
N1 C2 C10 108.79(13) . . ?
C10 C2 C1 129.60(13) . . ?
N1 C3 C4 127.42(13) . . ?
N1 C3 C8 106.68(12) . . ?
C4 C3 C8 125.90(13) . . ?
C3 C4 H4 114.9 . . ?
C5 C4 C3 130.15(14) . . ?
C5 C4 H4 114.9 . . ?
C4 C5 C6 120.12(13) . . ?
C4 C5 C7 123.12(13) . . ?
C7 C5 C6 116.73(13) . . ?
N2 C6 C5 179.45(18) . . ?
N3 C7 C5 178.40(16) . . ?
C3 C8 C9 125.27(13) . . ?
C10 C8 C3 107.78(12) . . ?
C10 C8 C9 126.94(13) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 C8 107.16(13) . . ?
C2 C10 C11 125.78(13) . . ?
C8 C10 C11 127.05(13) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
N1 C2 C10 C8 0.35(16) . . . . ?
N1 C2 C10 C11 -179.03(13) . . . . ?
N1 C3 C4 C5 -2.1(3) . . . . ?
N1 C3 C8 C9 179.18(13) . . . . ?
N1 C3 C8 C10 0.09(16) . . . . ?
C1 C2 C10 C8 -179.42(14) . . . . ?
C1 C2 C10 C11 1.2(2) . . . . ?
C2 N1 C3 C4 179.18(14) . . . . ?
C2 N1 C3 C8 0.12(16) . . . . ?
C3 N1 C2 C1 179.50(13) . . . . ?
C3 N1 C2 C10 -0.29(17) . . . . ?
C3 C4 C5 C6 -179.11(15) . . . . ?
C3 C4 C5 C7 -1.0(3) . . . . ?
C3 C8 C10 C2 -0.27(16) . . . . ?
C3 C8 C10 C11 179.10(14) . . . . ?
C4 C3 C8 C9 0.1(2) . . . . ?
C4 C3 C8 C10 -178.98(14) . . . . ?
C8 C3 C4 C5 176.79(15) . . . . ?
C9 C8 C10 C2 -179.34(14) . . . . ?
C9 C8 C10 C11 0.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
