# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_11277
_audit_block_doi                 10.5517/ccdc.csd.cc26j2b5
_database_code_depnum_ccdc_archive 'CCDC 2041236'
loop_
_audit_author_name
_audit_author_address
'Mengzhu Guo'
;Qingdao Agricultural University
China
;
_audit_update_record             
;
2020-10-29 deposited with the CCDC.	2021-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H18 N4'
_chemical_formula_weight         350.41

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9882(4)
_cell_length_b                   10.1351(7)
_cell_length_c                   11.5052(5)
_cell_angle_alpha                93.836(4)
_cell_angle_beta                 96.860(4)
_cell_angle_gamma                90.014(5)
_cell_volume                     922.70(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9314
_exptl_absorpt_correction_T_max  0.9369
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5652
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.88
_diffrn_reflns_theta_max         67.25
_reflns_number_total             3308
_reflns_number_gt                2539
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0506P)²+0.2761P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3308
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1485
_refine_ls_wR_factor_gt          0.1391
_refine_ls_goodness_of_fit_ref   1.204
_refine_ls_restrained_S_all      1.204
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3384(2) 0.73840(19) 0.06891(15) 0.0432(4) Uani 1 1 d . . .
N2 N 0.9408(3) 0.9981(3) -0.21438(19) 0.0668(6) Uani 1 1 d . . .
N3 N 0.9713(3) 0.6165(3) 0.3146(2) 0.0765(7) Uani 1 1 d . . .
N4 N 0.7958(3) 0.6859(3) 0.65138(19) 0.0718(7) Uani 1 1 d . . .
C1 C 0.3793(3) 0.6791(3) 0.5255(2) 0.0516(6) Uani 1 1 d . . .
H1 H 0.4322 0.5982 0.5349 0.062 Uiso 1 1 calc R . .
C2 C 0.2498(3) 0.7148(3) 0.5905(2) 0.0588(7) Uani 1 1 d . . .
H2 H 0.2138 0.6565 0.6416 0.071 Uiso 1 1 calc R . .
C3 C 0.1740(3) 0.8352(3) 0.5804(2) 0.0614(7) Uani 1 1 d . . .
H3 H 0.0897 0.8600 0.6265 0.074 Uiso 1 1 calc R . .
C4 C 0.2231(3) 0.9191(3) 0.5016(3) 0.0673(7) Uani 1 1 d . . .
H4 H 0.1711 1.0007 0.4938 0.081 Uiso 1 1 calc R . .
C5 C 0.3490(3) 0.8829(3) 0.4342(2) 0.0567(6) Uani 1 1 d . . .
H5 H 0.3796 0.9395 0.3798 0.068 Uiso 1 1 calc R . .
C6 C 0.4305(3) 0.7633(2) 0.44653(18) 0.0421(5) Uani 1 1 d . . .
C7 C 0.5706(3) 0.7302(2) 0.37553(18) 0.0419(5) Uani 1 1 d . . .
C8 C 0.5408(3) 0.7444(2) 0.24839(18) 0.0421(5) Uani 1 1 d . . .
C9 C 0.3820(3) 0.6811(2) 0.18248(19) 0.0471(6) Uani 1 1 d . . .
H9 H 0.2892 0.6987 0.2297 0.057 Uiso 1 1 calc R . .
C10 C 0.4568(3) 0.7892(2) 0.00866(18) 0.0389(5) Uani 1 1 d . . .
C11 C 0.4227(3) 0.8209(2) -0.10890(19) 0.0456(5) Uani 1 1 d . . .
H11 H 0.3146 0.8070 -0.1478 0.055 Uiso 1 1 calc R . .
C12 C 0.5450(3) 0.8716(2) -0.16738(19) 0.0459(5) Uani 1 1 d . . .
H12 H 0.5198 0.8889 -0.2459 0.055 Uiso 1 1 calc R . .
C13 C 0.7072(3) 0.8975(2) -0.11051(18) 0.0428(5) Uani 1 1 d . . .
C14 C 0.7413(3) 0.8727(2) 0.00684(18) 0.0433(5) Uani 1 1 d . . .
H14 H 0.8477 0.8927 0.0462 0.052 Uiso 1 1 calc R . .
C15 C 0.6208(2) 0.8189(2) 0.06686(18) 0.0386(5) Uani 1 1 d . . .
C16 C 0.6525(3) 0.8029(2) 0.19068(18) 0.0434(5) Uani 1 1 d . . .
H16 H 0.7536 0.8342 0.2318 0.052 Uiso 1 1 calc R . .
C17 C 0.4053(4) 0.5315(3) 0.1686(3) 0.0824(10) Uani 1 1 d . . .
H17A H 0.3009 0.4903 0.1348 0.124 Uiso 1 1 calc R . .
H17B H 0.4390 0.4985 0.2441 0.124 Uiso 1 1 calc R . .
H17C H 0.4907 0.5117 0.1181 0.124 Uiso 1 1 calc R . .
C18 C 0.1629(3) 0.7235(3) 0.0154(2) 0.0586(7) Uani 1 1 d . . .
H18A H 0.1295 0.8044 -0.0213 0.070 Uiso 1 1 calc R . .
H18B H 0.0922 0.7133 0.0772 0.070 Uiso 1 1 calc R . .
C19 C 0.1283(4) 0.6083(4) -0.0754(3) 0.0811(10) Uani 1 1 d . . .
H19A H 0.2041 0.6128 -0.1337 0.122 Uiso 1 1 calc R . .
H19B H 0.0141 0.6125 -0.1120 0.122 Uiso 1 1 calc R . .
H19C H 0.1446 0.5267 -0.0379 0.122 Uiso 1 1 calc R . .
C20 C 0.8358(3) 0.9527(3) -0.1699(2) 0.0489(6) Uani 1 1 d . . .
C21 C 0.7226(3) 0.6899(2) 0.42754(19) 0.0451(5) Uani 1 1 d . . .
C22 C 0.8597(3) 0.6487(3) 0.3628(2) 0.0532(6) Uani 1 1 d . . .
C23 C 0.7605(3) 0.6875(3) 0.5525(2) 0.0512(6) Uani 1 1 d . . .


_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 C10 1.358(3) . ?
N1 C18 1.466(3) . ?
N1 C9 1.469(3) . ?
N2 C20 1.144(3) . ?
N3 C22 1.141(3) . ?
N4 C23 1.140(3) . ?
C1 C2 1.381(3) . ?
C1 C6 1.383(3) . ?
C2 C3 1.368(4) . ?
C3 C4 1.373(4) . ?
C4 C5 1.378(4) . ?
C5 C6 1.384(3) . ?
C6 C7 1.488(3) . ?
C7 C21 1.364(3) . ?
C7 C8 1.470(3) . ?
C8 C16 1.335(3) . ?
C8 C9 1.517(3) . ?
C9 C17 1.528(4) . ?
C10 C11 1.406(3) . ?
C10 C15 1.421(3) . ?
C11 C12 1.369(3) . ?
C12 C13 1.396(3) . ?
C13 C14 1.385(3) . ?
C13 C20 1.434(3) . ?
C14 C15 1.382(3) . ?
C15 C16 1.437(3) . ?
C18 C19 1.515(4) . ?
C21 C23 1.435(3) . ?
C21 C22 1.443(3) . ?

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
C10 N1 C18 120.45(18) . . ?
C10 N1 C9 122.29(17) . . ?
C18 N1 C9 116.83(17) . . ?
C2 C1 C6 120.3(2) . . ?
C3 C2 C1 120.6(2) . . ?
C2 C3 C4 119.6(2) . . ?
C3 C4 C5 120.2(3) . . ?
C4 C5 C6 120.7(2) . . ?
C1 C6 C5 118.5(2) . . ?
C1 C6 C7 122.4(2) . . ?
C5 C6 C7 119.1(2) . . ?
C21 C7 C8 121.23(19) . . ?
C21 C7 C6 120.74(19) . . ?
C8 C7 C6 118.02(18) . . ?
C16 C8 C7 122.18(19) . . ?
C16 C8 C9 120.47(19) . . ?
C7 C8 C9 117.22(18) . . ?
N1 C9 C8 111.16(18) . . ?
N1 C9 C17 112.0(2) . . ?
C8 C9 C17 109.3(2) . . ?
N1 C10 C11 122.90(19) . . ?
N1 C10 C15 119.60(18) . . ?
C11 C10 C15 117.42(19) . . ?
C12 C11 C10 121.5(2) . . ?
C11 C12 C13 120.8(2) . . ?
C14 C13 C12 118.66(19) . . ?
C14 C13 C20 119.9(2) . . ?
C12 C13 C20 121.4(2) . . ?
C15 C14 C13 121.5(2) . . ?
C14 C15 C10 120.04(19) . . ?
C14 C15 C16 121.25(19) . . ?
C10 C15 C16 118.48(18) . . ?
C8 C16 C15 121.8(2) . . ?
N1 C18 C19 115.4(2) . . ?
N2 C20 C13 178.1(3) . . ?
C7 C21 C23 122.4(2) . . ?
C7 C21 C22 123.4(2) . . ?
C23 C21 C22 114.3(2) . . ?
N3 C22 C21 178.0(3) . . ?
N4 C23 C21 177.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        67.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.034
