# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_1
_audit_block_doi                 10.5517/ccdc.csd.cc25x8bq
_database_code_depnum_ccdc_archive 'CCDC 2023163'
loop_
_audit_author_name
_audit_author_address
'Jian Huanng'
;Jiangxi Normal University
China
;
_audit_update_record             
;
2020-08-13 deposited with the CCDC.	2020-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H18 N2'
_chemical_formula_sum            'C27 H18 N2'
_chemical_formula_weight         370.43

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

loop_
_symmetry_equiv_pos_as_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                   11.8524(8)
_cell_length_b                   12.1284(8)
_cell_length_c                   14.3084(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.050(7)
_cell_angle_gamma                90.00
_cell_volume                     1966.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4500
_cell_measurement_theta_min      3.8800
_cell_measurement_theta_max      27.1090

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   'MULTI SCAN'
_exptl_absorpt_correction_T_min  0.63675
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13002
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3433
_reflns_number_gt                2677
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0453P)²+0.4852P] 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         3433
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1168
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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 0.61253(12) 0.30689(11) 0.43571(10) 0.0415(4) Uani 1 1 d . . .
N2 N 0.67044(13) 0.23014(12) 0.50111(10) 0.0472(4) Uani 1 1 d . . .
C5 C 0.49013(15) 0.32008(14) 0.41174(12) 0.0408(4) Uani 1 1 d . . .
C4 C 0.43899(15) 0.40131(14) 0.34822(12) 0.0430(4) Uani 1 1 d . . .
C1 C 0.68497(15) 0.37295(14) 0.39956(12) 0.0422(4) Uani 1 1 d . . .
C22 C 0.42562(14) 0.24248(14) 0.45819(12) 0.0411(4) Uani 1 1 d . . .
C7 C 0.79995(15) 0.33599(14) 0.44656(12) 0.0437(4) Uani 1 1 d . . .
C2 C 0.63232(16) 0.45543(14) 0.32925(12) 0.0461(4) Uani 1 1 d . . .
C3 C 0.50896(16) 0.47093(14) 0.30427(12) 0.0458(4) Uani 1 1 d . . .
C16 C 0.30800(16) 0.41563(14) 0.31952(12) 0.0446(4) Uani 1 1 d . . .
C6 C 0.78483(15) 0.24754(14) 0.50688(13) 0.0456(4) Uani 1 1 d . . .
C23 C 0.37265(16) 0.27924(16) 0.52636(13) 0.0519(5) Uani 1 1 d . . .
H23 H 0.3788 0.3529 0.5451 0.062 Uiso 1 1 calc R . .
C8 C 0.91527(17) 0.36746(16) 0.44853(14) 0.0551(5) Uani 1 1 d . . .
H8 H 0.9272 0.4257 0.4102 0.066 Uiso 1 1 calc R . .
C27 C 0.41566(17) 0.13222(15) 0.43203(14) 0.0553(5) Uani 1 1 d . . .
H27 H 0.4523 0.1062 0.3871 0.066 Uiso 1 1 calc R . .
C21 C 0.23494(17) 0.34024(16) 0.25823(14) 0.0549(5) Uani 1 1 d . . .
H21 H 0.2675 0.2794 0.2362 0.066 Uiso 1 1 calc R . .
C11 C 0.88308(17) 0.18957(17) 0.56581(15) 0.0582(5) Uani 1 1 d . . .
H11 H 0.8733 0.1306 0.6042 0.070 Uiso 1 1 calc R . .
C17 C 0.25704(18) 0.50539(17) 0.35115(14) 0.0590(5) Uani 1 1 d . . .
H17 H 0.3050 0.5573 0.3918 0.071 Uiso 1 1 calc R . .
C15 C 0.4572(2) 0.55185(16) 0.23450(14) 0.0604(5) Uani 1 1 d . . .
H15 H 0.3762 0.5633 0.2175 0.072 Uiso 1 1 calc R . .
C24 C 0.31044(17) 0.2062(2) 0.56665(15) 0.0646(6) Uani 1 1 d . . .
H24 H 0.2756 0.2311 0.6131 0.078 Uiso 1 1 calc R . .
C19 C 0.06517(18) 0.4435(2) 0.26221(14) 0.0642(6) Uani 1 1 d . . .
H19 H -0.0163 0.4526 0.2430 0.077 Uiso 1 1 calc R . .
C9 C 1.00844(18) 0.31154(18) 0.50710(16) 0.0638(6) Uani 1 1 d . . .
H9 H 1.0846 0.3326 0.5092 0.077 Uiso 1 1 calc R . .
C25 C 0.29934(17) 0.0977(2) 0.53909(17) 0.0680(6) Uani 1 1 d . . .
H25 H 0.2562 0.0496 0.5659 0.082 Uiso 1 1 calc R . .
C26 C 0.35204(18) 0.06041(17) 0.47187(17) 0.0660(6) Uani 1 1 d . . .
H26 H 0.3450 -0.0133 0.4530 0.079 Uiso 1 1 calc R . .
C10 C 0.99236(18) 0.22217(18) 0.56496(16) 0.0657(6) Uani 1 1 d . . .
H10 H 1.0581 0.1847 0.6034 0.079 Uiso 1 1 calc R . .
C12 C 0.6990(2) 0.52077(17) 0.28368(15) 0.0641(6) Uani 1 1 d . . .
H12 H 0.7803 0.5115 0.3001 0.077 Uiso 1 1 calc R . .
C20 C 0.11445(18) 0.35452(19) 0.22958(15) 0.0642(6) Uani 1 1 d . . .
H20 H 0.0662 0.3036 0.1879 0.077 Uiso 1 1 calc R . .
C18 C 0.13629(19) 0.51889(19) 0.32318(15) 0.0656(6) Uani 1 1 d . . .
H18 H 0.1031 0.5791 0.3457 0.079 Uiso 1 1 calc R . .
C14 C 0.5242(2) 0.61387(19) 0.19137(16) 0.0759(7) Uani 1 1 d . . .
H14 H 0.4885 0.6672 0.1456 0.091 Uiso 1 1 calc R . .
C13 C 0.6450(2) 0.59777(19) 0.21545(17) 0.0783(7) Uani 1 1 d . . .
H13 H 0.6897 0.6397 0.1850 0.094 Uiso 1 1 calc R . .


_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 N2 1.3552(19) . ?
N1 C1 1.381(2) . ?
N1 C5 1.399(2) . ?
N2 C6 1.350(2) . ?
C5 C4 1.357(2) . ?
C5 C22 1.487(2) . ?
C4 C3 1.450(2) . ?
C4 C16 1.495(2) . ?
C1 C7 1.405(2) . ?
C1 C2 1.426(2) . ?
C22 C23 1.380(2) . ?
C22 C27 1.384(2) . ?
C7 C8 1.411(2) . ?
C7 C6 1.421(2) . ?
C2 C12 1.407(2) . ?
C2 C3 1.412(3) . ?
C3 C15 1.406(3) . ?
C16 C21 1.382(2) . ?
C16 C17 1.384(2) . ?
C6 C11 1.409(3) . ?
C23 C24 1.382(3) . ?
C23 H23 0.9300 . ?
C8 C9 1.356(3) . ?
C8 H8 0.9300 . ?
C27 C26 1.380(3) . ?
C27 H27 0.9300 . ?
C21 C20 1.376(3) . ?
C21 H21 0.9300 . ?
C11 C10 1.358(3) . ?
C11 H11 0.9300 . ?
C17 C18 1.378(3) . ?
C17 H17 0.9300 . ?
C15 C14 1.365(3) . ?
C15 H15 0.9300 . ?
C24 C25 1.369(3) . ?
C24 H24 0.9300 . ?
C19 C18 1.370(3) . ?
C19 C20 1.373(3) . ?
C19 H19 0.9300 . ?
C9 C10 1.410(3) . ?
C9 H9 0.9300 . ?
C25 C26 1.368(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C10 H10 0.9300 . ?
C12 C13 1.367(3) . ?
C12 H12 0.9300 . ?
C20 H20 0.9300 . ?
C18 H18 0.9300 . ?
C14 C13 1.384(3) . ?
C14 H14 0.9300 . ?
C13 H13 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
N2 N1 C1 114.36(14) . . ?
N2 N1 C5 121.80(13) . . ?
C1 N1 C5 123.77(14) . . ?
C6 N2 N1 103.36(13) . . ?
C4 C5 N1 118.36(15) . . ?
C4 C5 C22 124.88(15) . . ?
N1 C5 C22 116.77(14) . . ?
C5 C4 C3 120.89(16) . . ?
C5 C4 C16 119.49(15) . . ?
C3 C4 C16 119.55(15) . . ?
N1 C1 C7 104.95(15) . . ?
N1 C1 C2 118.66(15) . . ?
C7 C1 C2 136.39(16) . . ?
C23 C22 C27 118.87(17) . . ?
C23 C22 C5 120.79(16) . . ?
C27 C22 C5 120.33(16) . . ?
C1 C7 C8 136.15(17) . . ?
C1 C7 C6 104.73(15) . . ?
C8 C7 C6 119.08(17) . . ?
C12 C2 C3 119.22(17) . . ?
C12 C2 C1 122.21(18) . . ?
C3 C2 C1 118.57(16) . . ?
C15 C3 C2 118.44(17) . . ?
C15 C3 C4 121.92(17) . . ?
C2 C3 C4 119.61(16) . . ?
C21 C16 C17 118.40(18) . . ?
C21 C16 C4 120.30(16) . . ?
C17 C16 C4 121.28(16) . . ?
N2 C6 C11 126.68(17) . . ?
N2 C6 C7 112.59(16) . . ?
C11 C6 C7 120.72(17) . . ?
C22 C23 C24 119.80(19) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C9 C8 C7 119.04(18) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C26 C27 C22 120.77(19) . . ?
C26 C27 H27 119.6 . . ?
C22 C27 H27 119.6 . . ?
C20 C21 C16 120.54(19) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
C10 C11 C6 118.20(19) . . ?
C10 C11 H11 120.9 . . ?
C6 C11 H11 120.9 . . ?
C18 C17 C16 120.95(19) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C14 C15 C3 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C3 C15 H15 119.5 . . ?
C25 C24 C23 120.9(2) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C18 C19 C20 119.9(2) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C8 C9 C10 121.42(19) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C26 C25 C24 119.69(19) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 C27 119.9(2) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C11 C10 C9 121.5(2) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C13 C12 C2 120.5(2) . . ?
C13 C12 H12 119.8 . . ?
C2 C12 H12 119.8 . . ?
C19 C20 C21 120.4(2) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C19 C18 C17 119.9(2) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.032
