# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_sg-715
_database_code_depnum_ccdc_archive 'CCDC 2290138'
loop_
_audit_author_name
_audit_author_address
'Roman Alekseevich Dolotov'
;N D Zelinsky Institute of Organic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-08-22 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;
_audit_creation_date             2023-07-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 N3'
_chemical_formula_sum            'C14 H11 N3'
_chemical_formula_weight         221.26
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H11N3
_chemical_oxdiff_usercomment     SG-715
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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 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'

_cell_length_a                   5.76010(10)
_cell_length_b                   16.4872(3)
_cell_length_c                   11.6145(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.0990(10)
_cell_angle_gamma                90
_cell_volume                     1078.50(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4990
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      76.3840
_cell_measurement_theta_min      6.6240
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.925
_exptl_absorpt_coefficient_mu    0.662
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5838
_diffrn_reflns_point_group_measured_fraction_full 0.654
_diffrn_reflns_point_group_measured_fraction_max 0.637
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.086
_diffrn_reflns_theta_min         5.366
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00 -14.00   0.50    0.80    --  -88.50  45.00-120.00   74
  2  ω    -43.00  31.00   0.50    0.20    --  -44.78  38.00 -90.00  148
  3  ω    -51.00 -14.00   0.50    0.80    --  -88.50  45.00   0.00   74
  4  ω    -51.00 -14.00   0.50    0.80    --  -88.50  45.00  90.00   74
  5  ω    -26.00  34.00   0.50    0.20    --  -44.78  19.00 150.00  120
  6  ω    106.00 178.00   0.50    0.80    --  110.00 104.00 152.00  144
  7  ω     95.00 156.00   0.50    0.80    --  110.00 125.00 -60.00  122
  8  ω    151.00 178.00   0.50    0.80    --  110.00 125.00-120.00   54
  9  ω     95.00 178.00   0.50    0.80    --  110.00 125.00-150.00  166
 10  ω     90.00 178.00   0.50    0.80    --  110.00  30.00 -30.00  176
 11  ω     90.00 147.00   0.50    0.80    --  110.00  61.00 -90.00  114
 12  ω    120.00 166.00   0.50    0.80    --  110.00  61.00  30.00   92
 13  ω     73.00 101.00   0.50    0.80    --  110.00 -77.00  30.00   56
 14  ω     47.00  92.00   0.50    0.80    --  110.00 -77.00  60.00   90
 15  ω     37.00  71.00   0.50    0.80    --  110.00 -61.00 120.00   68
 16  ω     38.00  78.00   0.50    0.80    --  110.00 -77.00   0.00   80
 17  ω     40.00  83.00   0.50    0.80    --  110.00 -77.00 -30.00   86
 18  ω     37.00  71.00   0.50    0.80    --  110.00 -61.00 -60.00   68
 19  ω     42.00  68.00   0.50    0.80    --  110.00 -77.00-150.00   52
 20  ω     41.00  71.00   0.50    0.80    --  110.00 -61.00-150.00   60
 21  ω    -33.00  26.00   0.50    0.20    --   44.78 -19.00 -90.00  118
 22  ω     50.00  94.00   0.50    0.80    --  110.00-128.00 -11.37   88
 23  ω     38.00 106.00   0.50    0.80    --  110.00-104.00  50.00  136
 24  ω     74.00 107.00   0.50    0.80    --  110.00-125.00 -60.00   66
 25  ω     37.00 106.00   0.50    0.80    --  110.00 -95.00-120.00  138
 26  ω     39.00 112.00   0.50    0.80    --  110.00-125.00-150.00  146
 27  ω     39.00 112.00   0.50    0.80    --  110.00-125.00-180.00  146
 28  ω     41.00 100.00   0.50    0.80    --  110.00-105.00-166.61  118
 29  ω     18.00  84.00   0.50    0.20    --   44.78-104.00  50.00  132
 30  ω     67.00 103.00   0.50    0.80    --  110.00 -95.00  90.00   72
 31  ω    -81.00   3.00   0.50    0.20    --  -44.78 104.00 152.00  168
 32  ω    -81.00 -16.00   0.50    0.80    --  -88.50 104.00 152.00  130
 33  ω   -160.00 -84.00   0.50    0.80    --  -88.50-104.00  50.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1453188000
_diffrn_orient_matrix_UB_12      -0.0178824000
_diffrn_orient_matrix_UB_13      -0.1245760000
_diffrn_orient_matrix_UB_21      0.0369010000
_diffrn_orient_matrix_UB_22      0.0880176000
_diffrn_orient_matrix_UB_23      -0.0367014000
_diffrn_orient_matrix_UB_31      0.2287944000
_diffrn_orient_matrix_UB_32      -0.0257034000
_diffrn_orient_matrix_UB_33      -0.0392396000
_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         0.277
_reflns_Friedel_fraction_full    0.306
_reflns_Friedel_fraction_max     0.278
_reflns_number_gt                1435
_reflns_number_total             1451
_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 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 306 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         1451
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.056
_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)+(0.0595P)²+0.3128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0859
_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
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   mixed
_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_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 0.7196(3) 0.28420(10) 0.50016(14) 0.0171(4) Uani 1 1 d . . . . .
N2 N 0.3955(3) 0.36000(10) 0.44388(15) 0.0185(4) Uani 1 1 d . . . . .
N3 N -0.0143(3) 0.25043(11) 0.23557(18) 0.0256(4) Uani 1 1 d . . . . .
C1 C 0.6095(3) 0.35637(11) 0.51238(16) 0.0167(4) Uani 1 1 d . . . . .
C2 C 0.3692(4) 0.28598(12) 0.38619(18) 0.0184(4) Uani 1 1 d . . . . .
C3 C 0.5667(4) 0.23793(12) 0.42097(17) 0.0180(4) Uani 1 1 d . . . . .
C4 C 0.6203(4) 0.15285(13) 0.39268(19) 0.0243(5) Uani 1 1 d . . . . .
H4A H 0.491(6) 0.116(2) 0.406(3) 0.037(8) Uiso 1 1 d . . . . .
H4B H 0.636(7) 0.149(2) 0.308(4) 0.054(10) Uiso 1 1 d . . . . .
C5 C 0.8449(4) 0.12286(13) 0.46892(19) 0.0244(5) Uani 1 1 d . . . . .
H5 H 0.886253 0.067515 0.462421 0.029 Uiso 1 1 calc R U . . .
C6 C 0.9910(4) 0.16938(13) 0.54572(18) 0.0236(4) Uani 1 1 d . . . . .
H6 H 1.131009 0.145017 0.589980 0.028 Uiso 1 1 calc R U . . .
C7 C 0.9506(4) 0.25651(13) 0.56706(19) 0.0212(4) Uani 1 1 d . . . . .
H7A H 1.091(6) 0.2890(19) 0.549(3) 0.033(8) Uiso 1 1 d . . . . .
H7B H 0.967(5) 0.2662(17) 0.651(3) 0.026(7) Uiso 1 1 d . . . . .
C8 C 0.1571(4) 0.26624(12) 0.30287(18) 0.0197(4) Uani 1 1 d . . . . .
C9 C 0.7128(3) 0.41996(12) 0.59777(16) 0.0181(4) Uani 1 1 d . . . . .
C10 C 0.9287(4) 0.45790(12) 0.59541(18) 0.0209(4) Uani 1 1 d . . . . .
H10 H 1.016466 0.442693 0.538111 0.025 Uiso 1 1 calc R U . . .
C11 C 1.0150(4) 0.51836(12) 0.67777(19) 0.0226(4) Uani 1 1 d . . . . .
H11 H 1.160975 0.544597 0.675875 0.027 Uiso 1 1 calc R U . . .
C12 C 0.8881(4) 0.54016(12) 0.76224(17) 0.0220(4) Uani 1 1 d . . . . .
H12 H 0.948840 0.580601 0.818831 0.026 Uiso 1 1 calc R U . . .
C13 C 0.6726(4) 0.50297(12) 0.76421(17) 0.0215(4) Uani 1 1 d . . . . .
H13 H 0.585426 0.518346 0.821661 0.026 Uiso 1 1 calc R U . . .
C14 C 0.5846(4) 0.44329(12) 0.68218(17) 0.0194(4) Uani 1 1 d . . . . .
H14 H 0.436649 0.418208 0.683402 0.023 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 C1 1.370(2) . ?
N1 C3 1.365(3) . ?
N1 C7 1.466(3) . ?
N2 C1 1.321(2) . ?
N2 C2 1.385(3) . ?
N3 C8 1.153(3) . ?
C1 C9 1.480(3) . ?
C2 C3 1.375(3) . ?
C2 C8 1.428(3) . ?
C3 C4 1.488(3) . ?
C4 H4A 0.99(4) . ?
C4 H4B 1.01(4) . ?
C4 C5 1.491(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.333(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.484(3) . ?
C7 H7A 1.03(3) . ?
C7 H7B 0.97(3) . ?
C9 C10 1.397(3) . ?
C9 C14 1.399(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.399(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(3) . ?
C14 H14 0.9500 . ?

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
C1 N1 C7 127.16(17) . . ?
C3 N1 C1 107.94(16) . . ?
C3 N1 C7 124.66(18) . . ?
C1 N2 C2 104.17(16) . . ?
N1 C1 C9 123.72(17) . . ?
N2 C1 N1 111.76(17) . . ?
N2 C1 C9 124.41(17) . . ?
N2 C2 C8 121.30(19) . . ?
C3 C2 N2 111.45(18) . . ?
C3 C2 C8 127.25(18) . . ?
N1 C3 C2 104.66(17) . . ?
N1 C3 C4 122.77(18) . . ?
C2 C3 C4 132.47(19) . . ?
C3 C4 H4A 110(2) . . ?
C3 C4 H4B 109(2) . . ?
C3 C4 C5 112.09(18) . . ?
H4A C4 H4B 110(3) . . ?
C5 C4 H4A 107(2) . . ?
C5 C4 H4B 108(2) . . ?
C4 C5 H5 118.2 . . ?
C6 C5 C4 123.6(2) . . ?
C6 C5 H5 118.2 . . ?
C5 C6 H6 117.6 . . ?
C5 C6 C7 124.7(2) . . ?
C7 C6 H6 117.6 . . ?
N1 C7 C6 111.68(18) . . ?
N1 C7 H7A 113.2(18) . . ?
N1 C7 H7B 111.6(18) . . ?
C6 C7 H7A 108.2(18) . . ?
C6 C7 H7B 109.9(17) . . ?
H7A C7 H7B 102(3) . . ?
N3 C8 C2 179.9(3) . . ?
C10 C9 C1 122.60(17) . . ?
C10 C9 C14 119.55(18) . . ?
C14 C9 C1 117.84(17) . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.73(19) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.25(19) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.13(18) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.03(19) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.30(19) . . ?
C13 C14 H14 119.8 . . ?

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 C1 C9 C10 60.5(3) . . . . ?
N1 C1 C9 C14 -120.7(2) . . . . ?
N1 C3 C4 C5 5.7(3) . . . . ?
N2 C1 C9 C10 -123.7(2) . . . . ?
N2 C1 C9 C14 55.1(2) . . . . ?
N2 C2 C3 N1 -1.2(2) . . . . ?
N2 C2 C3 C4 175.0(2) . . . . ?
C1 N1 C3 C2 1.4(2) . . . . ?
C1 N1 C3 C4 -175.32(18) . . . . ?
C1 N1 C7 C6 169.06(18) . . . . ?
C1 N2 C2 C3 0.5(2) . . . . ?
C1 N2 C2 C8 179.99(18) . . . . ?
C1 C9 C10 C11 179.15(17) . . . . ?
C1 C9 C14 C13 -179.71(17) . . . . ?
C2 N2 C1 N1 0.4(2) . . . . ?
C2 N2 C1 C9 -175.88(17) . . . . ?
C2 C3 C4 C5 -169.9(2) . . . . ?
C3 N1 C1 N2 -1.2(2) . . . . ?
C3 N1 C1 C9 175.15(17) . . . . ?
C3 N1 C7 C6 -4.7(3) . . . . ?
C3 C4 C5 C6 -5.8(3) . . . . ?
C4 C5 C6 C7 0.6(4) . . . . ?
C5 C6 C7 N1 4.7(3) . . . . ?
C7 N1 C1 N2 -175.73(18) . . . . ?
C7 N1 C1 C9 0.6(3) . . . . ?
C7 N1 C3 C2 176.11(18) . . . . ?
C7 N1 C3 C4 -0.6(3) . . . . ?
C8 C2 C3 N1 179.4(2) . . . . ?
C8 C2 C3 C4 -4.4(4) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C9 C14 C13 -0.9(3) . . . . ?
C10 C11 C12 C13 -1.1(3) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C9 0.4(3) . . . . ?
C14 C9 C10 C11 0.4(3) . . . . ?

_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 1.910
_oxdiff_exptl_absorpt_empirical_full_min 0.476
