# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_245
_audit_block_doi                 10.5517/ccdc.csd.cc296g33
_database_code_depnum_ccdc_archive 'CCDC 2121364'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.orglett.1c04044 2022
loop_
_audit_author_name
_audit_author_address
XiangLiu
;GUANG DONG YAO KE DA XUE
China
;
_audit_update_record             
;
2021-11-10 deposited with the CCDC.	2022-03-24 downloaded from the CCDC.
;
_audit_creation_date             2021-06-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 N3'
_chemical_formula_sum            'C16 H11 N3'
_chemical_formula_weight         245.28
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.2924(7)
_cell_length_b                   10.5002(7)
_cell_length_c                   12.7692(10)
_cell_angle_alpha                90
_cell_angle_beta                 109.598(8)
_cell_angle_gamma                90
_cell_volume                     1173.74(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2416
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.0980
_cell_measurement_theta_min      2.5520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            bronze
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5153
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.374
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -37.00  60.00   1.00    1.20    --  -11.43  77.00   0.00   97
  2  ω    -86.00  17.00   1.00    1.20    --  -11.43 -77.00 -90.00  103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0800969000
_diffrn_orient_matrix_UB_12      0.0022541000
_diffrn_orient_matrix_UB_13      -0.0114161000
_diffrn_orient_matrix_UB_21      -0.0121272000
_diffrn_orient_matrix_UB_22      -0.0134715000
_diffrn_orient_matrix_UB_23      -0.0567190000
_diffrn_orient_matrix_UB_31      -0.0002668000
_diffrn_orient_matrix_UB_32      -0.0662099000
_diffrn_orient_matrix_UB_33      0.0111419000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1744
_reflns_number_total             2068
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.021(2)
_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   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2068
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.033
_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)+(0.0464P)²+0.2835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0980
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
;
_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
N1 N 0.59361(13) 0.66208(11) 0.50795(9) 0.0216(3) Uani 1 1 d . . . . .
N2 N 0.43503(13) 0.72126(11) 0.34477(9) 0.0211(3) Uani 1 1 d . . . . .
N3 N 0.51667(14) 0.62406(12) 0.32169(10) 0.0234(3) Uani 1 1 d . . . . .
C1 C 0.40903(16) 0.84282(14) 0.49719(12) 0.0214(4) Uani 1 1 d . . . . .
C2 C 0.45257(17) 0.87450(14) 0.60989(12) 0.0247(4) Uani 1 1 d . . . . .
H2 H 0.530823 0.829684 0.661677 0.030 Uiso 1 1 calc R U . . .
C3 C 0.38032(17) 0.97129(15) 0.64415(12) 0.0283(4) Uani 1 1 d . . . . .
H3 H 0.410898 0.992989 0.719045 0.034 Uiso 1 1 calc R U . . .
C4 C 0.26101(18) 1.03759(16) 0.56732(13) 0.0305(4) Uani 1 1 d . . . . .
H4 H 0.212075 1.102776 0.591520 0.037 Uiso 1 1 calc R U . . .
C5 C 0.21531(17) 1.00760(15) 0.45668(13) 0.0280(4) Uani 1 1 d . . . . .
H5 H 0.134909 1.051924 0.406433 0.034 Uiso 1 1 calc R U . . .
C6 C 0.28889(16) 0.91045(14) 0.41848(12) 0.0233(4) Uani 1 1 d . . . . .
C7 C 0.24703(17) 0.87906(14) 0.30258(12) 0.0256(4) Uani 1 1 d . . . . .
H7 H 0.167935 0.923484 0.251190 0.031 Uiso 1 1 calc R U . . .
C8 C 0.31939(16) 0.78721(14) 0.26685(12) 0.0249(4) Uani 1 1 d . . . . .
H8 H 0.292421 0.768387 0.191539 0.030 Uiso 1 1 calc R U . . .
C9 C 0.48185(15) 0.74311(14) 0.45629(11) 0.0199(3) Uani 1 1 d . . . . .
C10 C 0.60974(16) 0.59161(13) 0.42290(11) 0.0204(3) Uani 1 1 d . . . . .
C11 C 0.71890(16) 0.48636(14) 0.43778(12) 0.0218(3) Uani 1 1 d . . . . .
C12 C 0.81915(17) 0.45465(15) 0.54274(12) 0.0264(4) Uani 1 1 d . . . . .
H12 H 0.816873 0.499719 0.604861 0.032 Uiso 1 1 calc R U . . .
C13 C 0.92232(18) 0.35591(15) 0.55460(14) 0.0319(4) Uani 1 1 d . . . . .
H13 H 0.989149 0.334954 0.624847 0.038 Uiso 1 1 calc R U . . .
C14 C 0.92668(18) 0.28845(16) 0.46304(14) 0.0328(4) Uani 1 1 d . . . . .
H14 H 0.996984 0.222877 0.471593 0.039 Uiso 1 1 calc R U . . .
C15 C 0.82714(19) 0.31811(15) 0.35913(14) 0.0316(4) Uani 1 1 d . . . . .
H15 H 0.829410 0.272137 0.297455 0.038 Uiso 1 1 calc R U . . .
C16 C 0.72351(17) 0.41651(15) 0.34644(13) 0.0274(4) Uani 1 1 d . . . . .
H16 H 0.656198 0.436124 0.276015 0.033 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 C9 1.3335(18) . ?
N1 C10 1.3634(18) . ?
N2 N3 1.3616(17) . ?
N2 C8 1.3810(18) . ?
N2 C9 1.3617(17) . ?
N3 C10 1.3358(18) . ?
C1 C2 1.398(2) . ?
C1 C6 1.417(2) . ?
C1 C9 1.437(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.395(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.369(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.404(2) . ?
C6 C7 1.437(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.340(2) . ?
C8 H8 0.9300 . ?
C10 C11 1.469(2) . ?
C11 C12 1.392(2) . ?
C11 C16 1.391(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.375(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(2) . ?
C16 H16 0.9300 . ?

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
C9 N1 C10 103.16(11) . . ?
N3 N2 C8 125.13(12) . . ?
N3 N2 C9 110.30(11) . . ?
C9 N2 C8 124.57(12) . . ?
C10 N3 N2 102.05(11) . . ?
C2 C1 C6 119.87(13) . . ?
C2 C1 C9 122.59(13) . . ?
C6 C1 C9 117.54(13) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.15(14) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.34(14) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.61(15) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.49(14) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 119.50(13) . . ?
C5 C6 C1 118.52(13) . . ?
C5 C6 C7 121.98(14) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.49(14) . . ?
C8 C7 H7 119.3 . . ?
N2 C8 H8 120.9 . . ?
C7 C8 N2 118.26(13) . . ?
C7 C8 H8 120.9 . . ?
N1 C9 N2 109.42(12) . . ?
N1 C9 C1 131.98(13) . . ?
N2 C9 C1 118.60(12) . . ?
N1 C10 C11 124.13(13) . . ?
N3 C10 N1 115.07(13) . . ?
N3 C10 C11 120.80(12) . . ?
C12 C11 C10 120.97(13) . . ?
C16 C11 C10 120.17(13) . . ?
C16 C11 C12 118.85(14) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.96(14) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.50(15) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.02(15) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 119.91(15) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.75(15) . . ?
C15 C16 H16 119.6 . . ?

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 C10 C11 C12 -2.4(2) . . . . ?
N1 C10 C11 C16 177.58(13) . . . . ?
N2 N3 C10 N1 -0.57(15) . . . . ?
N2 N3 C10 C11 178.95(12) . . . . ?
N3 N2 C8 C7 178.59(13) . . . . ?
N3 N2 C9 N1 0.08(15) . . . . ?
N3 N2 C9 C1 179.89(12) . . . . ?
N3 C10 C11 C12 178.11(13) . . . . ?
N3 C10 C11 C16 -1.9(2) . . . . ?
C1 C2 C3 C4 1.1(2) . . . . ?
C1 C6 C7 C8 -0.2(2) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
C2 C1 C6 C7 178.70(13) . . . . ?
C2 C1 C9 N1 1.7(2) . . . . ?
C2 C1 C9 N2 -178.08(13) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C4 C5 C6 C1 1.2(2) . . . . ?
C4 C5 C6 C7 -178.07(14) . . . . ?
C5 C6 C7 C8 179.12(14) . . . . ?
C6 C1 C2 C3 -0.5(2) . . . . ?
C6 C1 C9 N1 -178.47(14) . . . . ?
C6 C1 C9 N2 1.78(19) . . . . ?
C6 C7 C8 N2 0.9(2) . . . . ?
C8 N2 N3 C10 -178.69(13) . . . . ?
C8 N2 C9 N1 179.06(12) . . . . ?
C8 N2 C9 C1 -1.1(2) . . . . ?
C9 N1 C10 N3 0.63(16) . . . . ?
C9 N1 C10 C11 -178.87(13) . . . . ?
C9 N2 N3 C10 0.28(14) . . . . ?
C9 N2 C8 C7 -0.2(2) . . . . ?
C9 C1 C2 C3 179.31(13) . . . . ?
C9 C1 C6 C5 179.51(13) . . . . ?
C9 C1 C6 C7 -1.2(2) . . . . ?
C10 N1 C9 N2 -0.40(14) . . . . ?
C10 N1 C9 C1 179.83(15) . . . . ?
C10 C11 C12 C13 -179.27(13) . . . . ?
C10 C11 C16 C15 179.19(13) . . . . ?
C11 C12 C13 C14 0.0(2) . . . . ?
C12 C11 C16 C15 -0.8(2) . . . . ?
C12 C13 C14 C15 -0.7(2) . . . . ?
C13 C14 C15 C16 0.6(2) . . . . ?
C14 C15 C16 C11 0.2(2) . . . . ?
C16 C11 C12 C13 0.7(2) . . . . ?

_olex2_date_sample_data_collection 2021-06-22
_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 1.476
_oxdiff_exptl_absorpt_empirical_full_min 0.510
