# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2290733'
loop_
_audit_author_name
_audit_author_address
'Zenghui Wu'
;Anhui University of Chinese Medicine
China
;
_audit_update_record             
;
2024-02-07 deposited with the CCDC.	2024-02-07 downloaded from the CCDC.
;
_audit_creation_date             2024-01-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H9 N3'
_chemical_formula_sum            'C11 H9 N3'
_chemical_formula_weight         183.21
_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 0.0033 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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   13.009(3)
_cell_length_b                   15.324(3)
_cell_length_c                   4.6638(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     929.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4412
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      26.672
_cell_measurement_theta_min      2.659
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1180
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            6472
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.054
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.650
_reflns_Friedel_fraction_full    0.850
_reflns_Friedel_fraction_max     0.850
_reflns_number_gt                1465
_reflns_number_total             1541
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 541 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -10.0(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1541
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0775
_refine_ls_restrained_S_all      1.053
_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)+(0.1660P)²+0.0826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2056
_refine_ls_wR_factor_ref         0.2102
_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:
 C4(H4), C3(H3), C11(H11), C8(H8), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
;
_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
N2 N 0.5997(2) 0.3174(2) 0.6521(8) 0.0515(9) Uani 1 1 d . . . . .
N1 N 0.6762(2) 0.2792(2) 0.5027(10) 0.0637(10) Uani 1 1 d . . . . .
N3 N 0.4277(3) 0.3815(3) 0.9267(11) 0.0707(11) Uani 1 1 d . . . . .
C5 C 0.5039(3) 0.2815(2) 0.5978(9) 0.0495(9) Uani 1 1 d . . . . .
C6 C 0.5208(3) 0.2145(2) 0.3998(8) 0.0507(10) Uani 1 1 d . . . . .
C7 C 0.6273(3) 0.2155(2) 0.3489(9) 0.0564(10) Uani 1 1 d . . . . .
C4 C 0.4200(3) 0.3175(3) 0.7428(12) 0.0603(11) Uani 1 1 d . . . . .
H4 H 0.3551 0.2945 0.7065 0.072 Uiso 1 1 calc R U . . .
C2 C 0.6107(3) 0.3850(3) 0.8409(11) 0.0631(12) Uani 1 1 d . . . . .
C3 C 0.5235(4) 0.4134(3) 0.9714(13) 0.0706(12) Uani 1 1 d . . . . .
H3 H 0.5302 0.4586 1.1030 0.085 Uiso 1 1 calc R U . . .
C11 C 0.4568(4) 0.1529(3) 0.2623(11) 0.0662(11) Uani 1 1 d . . . . .
H11 H 0.3865 0.1517 0.2978 0.079 Uiso 1 1 calc R U . . .
C8 C 0.6711(4) 0.1539(3) 0.1574(12) 0.0768(15) Uani 1 1 d . . . . .
H8 H 0.7415 0.1526 0.1229 0.092 Uiso 1 1 calc R U . . .
C9 C 0.6060(5) 0.0967(3) 0.0257(13) 0.0825(15) Uani 1 1 d . . . . .
H9 H 0.6333 0.0568 -0.1039 0.099 Uiso 1 1 calc R U . . .
C10 C 0.5006(4) 0.0954(3) 0.0765(14) 0.0741(13) Uani 1 1 d . . . . .
H10 H 0.4596 0.0548 -0.0176 0.089 Uiso 1 1 calc R U . . .
C1 C 0.7162(4) 0.4214(4) 0.8849(19) 0.0989(19) Uani 1 1 d . . . . .
H1A H 0.7605 0.3766 0.9588 0.148 Uiso 1 1 calc R U . . .
H1B H 0.7131 0.4689 1.0190 0.148 Uiso 1 1 calc R U . . .
H1C H 0.7428 0.4421 0.7053 0.148 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N2 0.0423(15) 0.0534(16) 0.059(2) 0.0138(14) 0.0000(13) -0.0007(11)
N1 0.0412(16) 0.074(2) 0.075(2) 0.0196(18) 0.0065(17) 0.0047(13)
N3 0.062(2) 0.069(2) 0.081(3) -0.006(2) 0.0061(18) 0.0105(16)
C5 0.0409(17) 0.0515(17) 0.056(2) 0.0106(16) -0.0012(16) 0.0014(12)
C6 0.0486(19) 0.0518(17) 0.052(2) 0.0097(15) 0.0017(16) 0.0038(14)
C7 0.054(2) 0.0606(19) 0.055(2) 0.0148(17) 0.0080(18) 0.0086(15)
C4 0.0474(19) 0.062(2) 0.071(3) 0.001(2) 0.0046(19) 0.0047(15)
C2 0.063(2) 0.0532(19) 0.074(3) 0.0118(19) -0.016(2) -0.0087(16)
C3 0.081(3) 0.058(2) 0.073(3) -0.0009(19) -0.004(2) 0.0054(19)
C11 0.068(2) 0.062(2) 0.068(3) 0.0037(19) -0.004(2) -0.0013(19)
C8 0.069(3) 0.084(3) 0.078(3) 0.021(3) 0.022(2) 0.025(2)
C9 0.115(4) 0.066(2) 0.067(3) 0.001(2) 0.009(3) 0.021(3)
C10 0.088(3) 0.063(2) 0.072(3) 0.001(2) -0.004(3) 0.005(2)
C1 0.081(3) 0.097(3) 0.119(5) 0.005(4) -0.023(3) -0.037(3)

_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
N2 N1 1.349(5) . ?
N2 C5 1.385(4) . ?
N2 C2 1.367(6) . ?
N1 C7 1.368(6) . ?
N3 C4 1.307(7) . ?
N3 C3 1.355(6) . ?
C5 C6 1.398(5) . ?
C5 C4 1.397(5) . ?
C6 C7 1.406(6) . ?
C6 C11 1.413(6) . ?
C7 C8 1.419(7) . ?
C4 H4 0.9300 . ?
C2 C3 1.358(7) . ?
C2 C1 1.497(6) . ?
C3 H3 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.361(8) . ?
C8 H8 0.9300 . ?
C8 C9 1.365(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.392(8) . ?
C10 H10 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
N1 N2 C5 113.4(3) . . ?
N1 N2 C2 125.8(3) . . ?
C2 N2 C5 120.8(3) . . ?
N2 N1 C7 103.7(3) . . ?
C4 N3 C3 116.2(4) . . ?
N2 C5 C6 105.7(3) . . ?
N2 C5 C4 117.2(4) . . ?
C4 C5 C6 137.0(4) . . ?
C5 C6 C7 105.0(3) . . ?
C5 C6 C11 134.3(4) . . ?
C7 C6 C11 120.7(4) . . ?
N1 C7 C6 112.2(4) . . ?
N1 C7 C8 128.2(4) . . ?
C6 C7 C8 119.7(4) . . ?
N3 C4 C5 123.6(4) . . ?
N3 C4 H4 118.2 . . ?
C5 C4 H4 118.2 . . ?
N2 C2 C1 117.8(5) . . ?
C3 C2 N2 116.4(4) . . ?
C3 C2 C1 125.8(5) . . ?
N3 C3 C2 125.7(5) . . ?
N3 C3 H3 117.1 . . ?
C2 C3 H3 117.1 . . ?
C6 C11 H11 120.8 . . ?
C10 C11 C6 118.4(5) . . ?
C10 C11 H11 120.8 . . ?
C7 C8 H8 121.3 . . ?
C9 C8 C7 117.4(4) . . ?
C9 C8 H8 121.3 . . ?
C8 C9 H9 118.5 . . ?
C8 C9 C10 123.0(5) . . ?
C10 C9 H9 118.5 . . ?
C11 C10 C9 120.8(5) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 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
N2 N1 C7 C6 0.6(4) . . . . ?
N2 N1 C7 C8 -178.9(4) . . . . ?
N2 C5 C6 C7 -0.1(4) . . . . ?
N2 C5 C6 C11 179.0(4) . . . . ?
N2 C5 C4 N3 -0.9(7) . . . . ?
N2 C2 C3 N3 -1.2(8) . . . . ?
N1 N2 C5 C6 0.5(4) . . . . ?
N1 N2 C5 C4 -179.7(4) . . . . ?
N1 N2 C2 C3 -179.3(4) . . . . ?
N1 N2 C2 C1 1.0(6) . . . . ?
N1 C7 C8 C9 -179.4(4) . . . . ?
C5 N2 N1 C7 -0.7(4) . . . . ?
C5 N2 C2 C3 0.7(6) . . . . ?
C5 N2 C2 C1 -179.0(4) . . . . ?
C5 C6 C7 N1 -0.3(4) . . . . ?
C5 C6 C7 C8 179.2(4) . . . . ?
C5 C6 C11 C10 -179.9(5) . . . . ?
C6 C5 C4 N3 178.8(4) . . . . ?
C6 C7 C8 C9 1.2(6) . . . . ?
C6 C11 C10 C9 0.7(8) . . . . ?
C7 C6 C11 C10 -0.9(6) . . . . ?
C7 C8 C9 C10 -1.5(7) . . . . ?
C4 N3 C3 C2 0.6(8) . . . . ?
C4 C5 C6 C7 -179.8(5) . . . . ?
C4 C5 C6 C11 -0.7(8) . . . . ?
C2 N2 N1 C7 179.3(4) . . . . ?
C2 N2 C5 C6 -179.5(3) . . . . ?
C2 N2 C5 C4 0.2(5) . . . . ?
C3 N3 C4 C5 0.5(7) . . . . ?
C11 C6 C7 N1 -179.5(4) . . . . ?
C11 C6 C7 C8 0.0(5) . . . . ?
C8 C9 C10 C11 0.6(8) . . . . ?
C1 C2 C3 N3 178.5(6) . . . . ?

_shelx_res_file                  
;
    a.res created by SHELXL-2014/7

TITL a_a.res in Pna2(1)
REM Old TITL A in Pna2(1)
REM SHELXT solution in Pna2(1)
REM R1 0.141, Rweak 0.020, Alpha 0.001, Orientation as input
REM Flack x = -8.242 ( 9.990 ) from Parsons' quotients
REM Formula found by SHELXT: C12 N2
CELL 0.71073 13.009 15.3241 4.6638 90 90 90
ZERR 4 0.0025 0.003 0.0009 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,+Z
SYMM 0.5-X,0.5+Y,0.5+Z
SFAC C H N
UNIT 44 36 12

L.S. 4 0 0
PLAN  1
SIZE 0.18 0.19 0.18
TEMP 20
CONF
BOND $H
list 4
MORE -1
fmap 2 53
acta
OMIT -3 50
OMIT 0 3 1
REM <olex2.extras>
REM <HklSrc "%.\\A.hkl">
REM </olex2.extras>

WGHT    0.166000    0.082600
FVAR       0.74101
N2    3    0.599667    0.317420    0.652061    11.00000    0.04227    0.05336 =
         0.05878    0.01376    0.00001   -0.00067
N1    3    0.676214    0.279198    0.502710    11.00000    0.04115    0.07435 =
         0.07546    0.01957    0.00653    0.00471
N3    3    0.427655    0.381524    0.926663    11.00000    0.06242    0.06892 =
         0.08077   -0.00643    0.00605    0.01046
C5    1    0.503901    0.281511    0.597836    11.00000    0.04094    0.05154 =
         0.05601    0.01064   -0.00117    0.00140
C6    1    0.520804    0.214534    0.399822    11.00000    0.04856    0.05181 =
         0.05175    0.00971    0.00167    0.00379
C7    1    0.627327    0.215518    0.348922    11.00000    0.05352    0.06057 =
         0.05498    0.01478    0.00800    0.00855
C4    1    0.419962    0.317451    0.742816    11.00000    0.04744    0.06233 =
         0.07122    0.00138    0.00463    0.00467
AFIX  43
H4    2    0.355059    0.294531    0.706523    11.00000   -1.20000
AFIX   0
C2    1    0.610656    0.384999    0.840901    11.00000    0.06260    0.05316 =
         0.07365    0.01180   -0.01564   -0.00873
C3    1    0.523498    0.413368    0.971411    11.00000    0.08082    0.05758 =
         0.07340   -0.00091   -0.00371    0.00541
AFIX  43
H3    2    0.530187    0.458610    1.103006    11.00000   -1.20000
AFIX   0
C11   1    0.456835    0.152912    0.262269    11.00000    0.06816    0.06226 =
         0.06829    0.00368   -0.00358   -0.00130
AFIX  43
H11   2    0.386509    0.151674    0.297848    11.00000   -1.20000
AFIX   0
C8    1    0.671139    0.153914    0.157370    11.00000    0.06872    0.08352 =
         0.07822    0.02148    0.02189    0.02535
AFIX  43
H8    2    0.741533    0.152556    0.122895    11.00000   -1.20000
AFIX   0
C9    1    0.605997    0.096735    0.025678    11.00000    0.11500    0.06579 =
         0.06676    0.00130    0.00888    0.02099
AFIX  43
H9    2    0.633291    0.056843   -0.103886    11.00000   -1.20000
AFIX   0
C10   1    0.500603    0.095419    0.076482    11.00000    0.08775    0.06309 =
         0.07155    0.00103   -0.00401    0.00535
AFIX  43
H10   2    0.459613    0.054777   -0.017634    11.00000   -1.20000
AFIX   0
C1    1    0.716245    0.421427    0.884929    11.00000    0.08063    0.09665 =
         0.11942    0.00535   -0.02278   -0.03670
AFIX 137
H1A   2    0.760533    0.376641    0.958786    11.00000   -1.50000
H1B   2    0.713142    0.468899    1.018965    11.00000   -1.50000
H1C   2    0.742780    0.442105    0.705274    11.00000   -1.50000
AFIX   0
HKLF 4

REM  a_a.res in Pna2(1)
REM R1 =  0.0775 for    1465 Fo > 4sig(Fo)  and  0.0792 for all    1541 data
REM    128 parameters refined using      1 restraints

END

WGHT      0.1660      0.0826

REM Highest difference peak  0.185,  deepest hole -0.205,  1-sigma level  0.058
Q1    1   0.4825  0.3258  1.1729  11.00000  0.05    0.18
;
_shelx_res_checksum              94100
_olex2_submission_special_instructions 'No special instructions were received'
