# Supplementary Information (SI) 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_mo_20141115a_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2759b2
_database_code_depnum_ccdc_archive 'CCDC 2060673'
loop_
_audit_author_name
_audit_author_address
'Jiang-Xi Yu'
;Hengyang Normal University
China
;
_audit_update_record             
;
2021-02-02 deposited with the CCDC.	2024-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H22 N2'
_chemical_formula_sum            'C28 H22 N2'
_chemical_formula_weight         386.48

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   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_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'
'-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                   37.838(9)
_cell_length_b                   5.7784(14)
_cell_length_c                   19.980(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.615(4)
_cell_angle_gamma                90.00
_cell_volume                     4140.0(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3832
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      25.23

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1632
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9821
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_diffrn_ambient_temperature      298(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  'Bruker APEX II area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16356
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4063
_reflns_number_gt                3403
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'

_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)+(0.0642P)²+2.7171P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4063
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1316
_refine_ls_wR_factor_gt          0.1260
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.17298(3) 0.2662(2) 0.12161(6) 0.0401(3) Uani 1 1 d . . .
H1A H 0.1924 0.1788 0.1348 0.048 Uiso 1 1 calc R . .
N2 N 0.11422(4) 0.7348(2) 0.13875(7) 0.0448(3) Uani 1 1 d . . .
H2A H 0.1167 0.8655 0.1202 0.054 Uiso 1 1 calc R . .
C1 C 0.21782(5) 0.3256(3) 0.26859(8) 0.0463(4) Uani 1 1 d . . .
H1 H 0.2203 0.1896 0.2455 0.056 Uiso 1 1 calc R . .
C2 C 0.24074(5) 0.3631(4) 0.33729(9) 0.0523(4) Uani 1 1 d . . .
H2 H 0.2584 0.2523 0.3598 0.063 Uiso 1 1 calc R . .
C3 C 0.23757(5) 0.5631(4) 0.37239(9) 0.0521(4) Uani 1 1 d . . .
H3 H 0.2527 0.5870 0.4187 0.062 Uiso 1 1 calc R . .
C4 C 0.21168(5) 0.7279(4) 0.33808(10) 0.0543(5) Uani 1 1 d . . .
H4 H 0.2097 0.8644 0.3613 0.065 Uiso 1 1 calc R . .
C5 C 0.18865(5) 0.6921(3) 0.26943(9) 0.0487(4) Uani 1 1 d . . .
H5 H 0.1714 0.8048 0.2471 0.058 Uiso 1 1 calc R . .
C6 C 0.19109(4) 0.4889(3) 0.23344(8) 0.0395(4) Uani 1 1 d . . .
C7 C 0.16594(4) 0.4432(3) 0.16166(8) 0.0395(4) Uani 1 1 d . . .
C8 C 0.13214(4) 0.5394(3) 0.12148(8) 0.0399(4) Uani 1 1 d . . .
C9 C 0.11843(4) 0.4131(3) 0.05705(8) 0.0399(4) Uani 1 1 d . . .
C10 C 0.14500(4) 0.2466(3) 0.05770(8) 0.0382(4) Uani 1 1 d . . .
C11 C 0.14871(4) 0.0852(3) 0.00356(8) 0.0368(3) Uani 1 1 d . . .
C12 C 0.16932(4) -0.1192(3) 0.02239(9) 0.0437(4) Uani 1 1 d . . .
H12 H 0.1801 -0.1560 0.0699 0.052 Uiso 1 1 calc R . .
C13 C 0.17386(5) -0.2670(3) -0.02857(10) 0.0525(4) Uani 1 1 d . . .
H13 H 0.1880 -0.4008 -0.0151 0.063 Uiso 1 1 calc R . .
C14 C 0.15747(5) -0.2173(3) -0.09936(10) 0.0539(5) Uani 1 1 d . . .
H14 H 0.1604 -0.3173 -0.1337 0.065 Uiso 1 1 calc R . .
C15 C 0.13668(5) -0.0176(3) -0.11870(9) 0.0511(4) Uani 1 1 d . . .
H15 H 0.1253 0.0155 -0.1663 0.061 Uiso 1 1 calc R . .
C16 C 0.13249(4) 0.1337(3) -0.06826(8) 0.0441(4) Uani 1 1 d . . .
H16 H 0.1188 0.2688 -0.0822 0.053 Uiso 1 1 calc R . .
C17 C 0.08107(4) 0.4487(3) 0.00326(8) 0.0396(4) Uani 1 1 d . . .
C18 C 0.07206(5) 0.6509(3) -0.03584(9) 0.0477(4) Uani 1 1 d . . .
H18 H 0.0901 0.7656 -0.0298 0.057 Uiso 1 1 calc R . .
C19 C 0.03671(6) 0.6859(4) -0.08383(10) 0.0603(5) Uani 1 1 d . . .
H19 H 0.0313 0.8227 -0.1096 0.072 Uiso 1 1 calc R . .
C20 C 0.00942(5) 0.5155(4) -0.09335(10) 0.0597(5) Uani 1 1 d . . .
H20 H -0.0144 0.5371 -0.1252 0.072 Uiso 1 1 calc R . .
C21 C 0.01842(5) 0.3156(4) -0.05471(10) 0.0573(5) Uani 1 1 d . . .
H21 H 0.0004 0.2008 -0.0605 0.069 Uiso 1 1 calc R . .
C22 C 0.05376(5) 0.2812(3) -0.00722(9) 0.0519(4) Uani 1 1 d . . .
H22 H 0.0592 0.1433 0.0180 0.062 Uiso 1 1 calc R . .
C23 C 0.09277(4) 0.7288(3) 0.18386(8) 0.0389(4) Uani 1 1 d . . .
C24 C 0.06993(5) 0.9169(3) 0.18555(9) 0.0464(4) Uani 1 1 d . . .
H24 H 0.0687 1.0427 0.1559 0.056 Uiso 1 1 calc R . .
C25 C 0.04918(5) 0.9163(4) 0.23128(10) 0.0588(5) Uani 1 1 d . . .
H25 H 0.0340 1.0425 0.2319 0.071 Uiso 1 1 calc R . .
C26 C 0.05044(6) 0.7333(4) 0.27594(10) 0.0632(5) Uani 1 1 d . . .
H26 H 0.0364 0.7346 0.3065 0.076 Uiso 1 1 calc R . .
C27 C 0.07294(5) 0.5492(4) 0.27431(9) 0.0543(5) Uani 1 1 d . . .
H27 H 0.0740 0.4249 0.3045 0.065 Uiso 1 1 calc R . .
C28 C 0.09417(4) 0.5414(3) 0.22935(8) 0.0441(4) Uani 1 1 d . . .
H28 H 0.1092 0.4139 0.2293 0.053 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 C7 1.376(2) . ?
N1 C10 1.3787(19) . ?
N1 H1A 0.8600 . ?
N2 C23 1.393(2) . ?
N2 C8 1.415(2) . ?
N2 H2A 0.8600 . ?
C1 C2 1.387(2) . ?
C1 C6 1.398(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.470(2) . ?
C7 C8 1.391(2) . ?
C8 C9 1.426(2) . ?
C9 C10 1.389(2) . ?
C9 C17 1.492(2) . ?
C10 C11 1.469(2) . ?
C11 C16 1.397(2) . ?
C11 C12 1.399(2) . ?
C12 C13 1.381(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.381(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.382(2) . ?
C17 C18 1.386(2) . ?
C18 C19 1.389(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.395(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.371(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.395(2) . ?
C23 C28 1.404(2) . ?
C24 C25 1.382(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.374(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.370(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.384(2) . ?
C27 H27 0.9300 . ?
C28 H28 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
C7 N1 C10 111.44(13) . . ?
C7 N1 H1A 124.3 . . ?
C10 N1 H1A 124.3 . . ?
C23 N2 C8 124.18(13) . . ?
C23 N2 H2A 117.9 . . ?
C8 N2 H2A 117.9 . . ?
C2 C1 C6 121.03(16) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C3 C2 C1 120.44(17) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.29(16) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 120.68(17) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.80(17) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 117.75(15) . . ?
C5 C6 C7 121.70(15) . . ?
C1 C6 C7 120.54(15) . . ?
N1 C7 C8 105.95(13) . . ?
N1 C7 C6 121.04(14) . . ?
C8 C7 C6 132.92(15) . . ?
C7 C8 N2 127.04(14) . . ?
C7 C8 C9 108.60(14) . . ?
N2 C8 C9 124.33(14) . . ?
C10 C9 C8 107.00(13) . . ?
C10 C9 C17 128.24(14) . . ?
C8 C9 C17 124.61(14) . . ?
N1 C10 C9 106.95(13) . . ?
N1 C10 C11 120.57(13) . . ?
C9 C10 C11 132.24(14) . . ?
C16 C11 C12 118.04(14) . . ?
C16 C11 C10 121.01(14) . . ?
C12 C11 C10 120.94(14) . . ?
C13 C12 C11 120.91(16) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 120.35(17) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.34(16) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.84(16) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C11 120.50(16) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C22 C17 C18 117.85(15) . . ?
C22 C17 C9 120.22(15) . . ?
C18 C17 C9 121.89(15) . . ?
C17 C18 C19 121.40(17) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C20 119.94(19) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 118.56(17) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C20 C21 C22 121.23(18) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C17 C22 C21 121.01(18) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
N2 C23 C24 119.33(15) . . ?
N2 C23 C28 121.91(14) . . ?
C24 C23 C28 118.74(15) . . ?
C25 C24 C23 120.07(17) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C26 C25 C24 121.45(18) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C27 C26 C25 118.39(17) . . ?
C27 C26 H26 120.8 . . ?
C25 C26 H26 120.8 . . ?
C26 C27 C28 122.30(18) . . ?
C26 C27 H27 118.8 . . ?
C28 C27 H27 118.8 . . ?
C27 C28 C23 119.05(16) . . ?
C27 C28 H28 120.5 . . ?
C23 C28 H28 120.5 . . ?

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
C6 C1 C2 C3 0.0(3) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C1 -0.9(2) . . . . ?
C4 C5 C6 C7 177.50(16) . . . . ?
C2 C1 C6 C5 0.9(2) . . . . ?
C2 C1 C6 C7 -177.53(15) . . . . ?
C10 N1 C7 C8 0.03(18) . . . . ?
C10 N1 C7 C6 176.95(14) . . . . ?
C5 C6 C7 N1 167.34(15) . . . . ?
C1 C6 C7 N1 -14.3(2) . . . . ?
C5 C6 C7 C8 -16.7(3) . . . . ?
C1 C6 C7 C8 161.67(17) . . . . ?
N1 C7 C8 N2 -176.40(14) . . . . ?
C6 C7 C8 N2 7.2(3) . . . . ?
N1 C7 C8 C9 1.44(18) . . . . ?
C6 C7 C8 C9 -174.94(16) . . . . ?
C23 N2 C8 C7 -81.0(2) . . . . ?
C23 N2 C8 C9 101.46(19) . . . . ?
C7 C8 C9 C10 -2.38(18) . . . . ?
N2 C8 C9 C10 175.54(14) . . . . ?
C7 C8 C9 C17 173.54(15) . . . . ?
N2 C8 C9 C17 -8.5(2) . . . . ?
C7 N1 C10 C9 -1.52(18) . . . . ?
C7 N1 C10 C11 173.49(14) . . . . ?
C8 C9 C10 N1 2.34(17) . . . . ?
C17 C9 C10 N1 -173.38(15) . . . . ?
C8 C9 C10 C11 -171.86(16) . . . . ?
C17 C9 C10 C11 12.4(3) . . . . ?
N1 C10 C11 C16 -148.39(15) . . . . ?
C9 C10 C11 C16 25.2(3) . . . . ?
N1 C10 C11 C12 30.1(2) . . . . ?
C9 C10 C11 C12 -156.33(17) . . . . ?
C16 C11 C12 C13 0.8(2) . . . . ?
C10 C11 C12 C13 -177.76(15) . . . . ?
C11 C12 C13 C14 -1.2(3) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C11 -1.2(3) . . . . ?
C12 C11 C16 C15 0.4(2) . . . . ?
C10 C11 C16 C15 178.92(15) . . . . ?
C10 C9 C17 C22 64.6(2) . . . . ?
C8 C9 C17 C22 -110.44(19) . . . . ?
C10 C9 C17 C18 -117.64(19) . . . . ?
C8 C9 C17 C18 67.3(2) . . . . ?
C22 C17 C18 C19 0.4(3) . . . . ?
C9 C17 C18 C19 -177.46(16) . . . . ?
C17 C18 C19 C20 0.1(3) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C19 C20 C21 C22 -0.2(3) . . . . ?
C18 C17 C22 C21 -0.7(3) . . . . ?
C9 C17 C22 C21 177.16(16) . . . . ?
C20 C21 C22 C17 0.6(3) . . . . ?
C8 N2 C23 C24 -166.24(15) . . . . ?
C8 N2 C23 C28 15.6(2) . . . . ?
N2 C23 C24 C25 -178.38(15) . . . . ?
C28 C23 C24 C25 -0.1(2) . . . . ?
C23 C24 C25 C26 0.1(3) . . . . ?
C24 C25 C26 C27 0.0(3) . . . . ?
C25 C26 C27 C28 -0.2(3) . . . . ?
C26 C27 C28 C23 0.2(3) . . . . ?
N2 C23 C28 C27 178.19(15) . . . . ?
C24 C23 C28 C27 0.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.037
