# Supplementary Information (SI) for Energy & Environmental Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 2409048'
loop_
_audit_author_name
_audit_author_address
'Jiajun Du'
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2024-12-10 deposited with the CCDC.	2025-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H20 N2'
_chemical_formula_sum            'C30 H20 N2'
_chemical_formula_weight         408.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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'
'-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                   27.8850(4)
_cell_length_b                   5.60720(10)
_cell_length_c                   27.8067(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.5670(10)
_cell_angle_gamma                90
_cell_volume                     4043.37(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    17772
_cell_measurement_theta_min      3.4160
_cell_measurement_theta_max      77.6600

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             1712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.605
_shelx_estimated_absorpt_T_min   0.909
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90472
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26979
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.409
_diffrn_reflns_theta_max         77.734
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4188
_reflns_number_gt                3884
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4188
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1574
_refine_ls_wR_factor_gt          0.1525
_refine_ls_goodness_of_fit_ref   1.421
_refine_ls_restrained_S_all      1.421
_refine_ls_shift/su_max          0.001
_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_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 -0.09351(3) -0.86611(17) 0.56085(4) 0.0282(2) Uani 1 1 d . . . . .
N8 N 0.17909(4) -1.82150(17) 0.81423(4) 0.0301(2) Uani 1 1 d . . . . .
H8 H 0.178464 -1.958001 0.829604 0.036 Uiso 1 1 d R U . . .
C1 C 0.06470(4) -1.4088(2) 0.70826(4) 0.0255(3) Uani 1 1 d . . . . .
C2 C -0.13664(4) -0.96726(19) 0.56718(4) 0.0265(3) Uani 1 1 d . . . . .
C3 C -0.18895(4) -0.9309(2) 0.53891(4) 0.0302(3) Uani 1 1 d . . . . .
H3 H -0.199989 -0.818686 0.512481 0.036 Uiso 1 1 calc R U . . .
C4 C -0.22392(4) -1.0682(2) 0.55163(4) 0.0312(3) Uani 1 1 d . . . . .
H4A H -0.259008 -1.044794 0.533657 0.037 Uiso 1 1 calc R U . . .
C5 C -0.20809(4) -1.2408(2) 0.59065(4) 0.0301(3) Uani 1 1 d . . . . .
H5 H -0.232561 -1.330752 0.598024 0.036 Uiso 1 1 calc R U . . .
C6 C -0.15597(4) -1.2783(2) 0.61839(4) 0.0282(3) Uani 1 1 d . . . . .
H6A H -0.145248 -1.393966 0.644122 0.034 Uiso 1 1 calc R U . . .
C7 C -0.11995(4) -1.13963(19) 0.60704(4) 0.0254(3) Uani 1 1 d . . . . .
C8 C -0.06439(4) -1.14435(19) 0.62516(4) 0.0260(3) Uani 1 1 d . . . . .
C9 C -0.04950(4) -0.9758(2) 0.59593(4) 0.0274(3) Uani 1 1 d . . . . .
C10 C -0.09476(4) -0.70679(19) 0.52062(4) 0.0258(3) Uani 1 1 d . . . . .
C11 C -0.06484(4) -0.7516(2) 0.49107(4) 0.0302(3) Uani 1 1 d . . . . .
H11A H -0.044248 -0.887288 0.497322 0.036 Uiso 1 1 calc R U . . .
C12 C -0.06574(4) -0.5940(2) 0.45231(5) 0.0343(3) Uani 1 1 d . . . . .
H12 H -0.044666 -0.620783 0.433558 0.041 Uiso 1 1 calc R U . . .
C13 C -0.09791(4) -0.3966(2) 0.44139(5) 0.0347(3) Uani 1 1 d . . . . .
H13 H -0.099166 -0.293487 0.414749 0.042 Uiso 1 1 calc R U . . .
C14 C -0.12819(4) -0.3537(2) 0.47035(5) 0.0328(3) Uani 1 1 d . . . . .
H14 H -0.149855 -0.221539 0.463025 0.039 Uiso 1 1 calc R U . . .
C15 C -0.12641(4) -0.5063(2) 0.51019(4) 0.0280(3) Uani 1 1 d . . . . .
H15 H -0.146331 -0.474891 0.529916 0.034 Uiso 1 1 calc R U . . .
C16 C 0.02474(4) -1.2547(2) 0.67059(4) 0.0264(3) Uani 1 1 d . . . . .
C17 C 0.03839(4) -1.0772(2) 0.64183(4) 0.0288(3) Uani 1 1 d . . . . .
H17 H 0.073147 -1.053683 0.647899 0.035 Uiso 1 1 calc R U . . .
C18 C 0.00244(4) -0.9369(2) 0.60508(4) 0.0299(3) Uani 1 1 d . . . . .
H18 H 0.012649 -0.820273 0.587050 0.036 Uiso 1 1 calc R U . . .
C19 C -0.02729(4) -1.2815(2) 0.66271(4) 0.0273(3) Uani 1 1 d . . . . .
H19 H -0.037350 -1.390538 0.682400 0.033 Uiso 1 1 calc R U . . .
C20 C 0.22260(4) -1.6857(2) 0.82176(4) 0.0268(3) Uani 1 1 d . . . . .
C21 C 0.20827(4) -1.48012(18) 0.79047(4) 0.0239(2) Uani 1 1 d . . . . .
C22 C 0.11679(4) -1.34467(19) 0.72781(4) 0.0251(2) Uani 1 1 d . . . . .
H22 H 0.127342 -1.202671 0.717495 0.030 Uiso 1 1 calc R U . . .
C23 C 0.15304(4) -1.49483(18) 0.76297(4) 0.0239(2) Uani 1 1 d . . . . .
C24 C 0.27359(4) -1.7290(2) 0.85396(5) 0.0305(3) Uani 1 1 d . . . . .
H24 H 0.282642 -1.865010 0.874475 0.037 Uiso 1 1 calc R U . . .
C25 C 0.05029(4) -1.6265(2) 0.72456(4) 0.0279(3) Uani 1 1 d . . . . .
H25 H 0.015797 -1.671555 0.710803 0.034 Uiso 1 1 calc R U . . .
C26 C 0.08503(4) -1.7758(2) 0.75998(4) 0.0288(3) Uani 1 1 d . . . . .
H26 H 0.074303 -1.916260 0.770744 0.035 Uiso 1 1 calc R U . . .
C27 C 0.13675(4) -1.70815(19) 0.77899(4) 0.0261(3) Uani 1 1 d . . . . .
C28 C 0.31017(4) -1.5618(2) 0.85420(5) 0.0320(3) Uani 1 1 d . . . . .
H28 H 0.344452 -1.586374 0.875319 0.038 Uiso 1 1 calc R U . . .
C29 C 0.24594(4) -1.3140(2) 0.79148(4) 0.0271(3) Uani 1 1 d . . . . .
H29 H 0.237091 -1.177448 0.771135 0.033 Uiso 1 1 calc R U . . .
C30 C 0.29681(4) -1.3558(2) 0.82333(5) 0.0309(3) Uani 1 1 d . . . . .
H30 H 0.322239 -1.246655 0.824240 0.037 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 C2 1.3981(14) . ?
N1 C9 1.3988(13) . ?
N1 C10 1.4219(14) . ?
N8 C27 1.3812(14) . ?
N8 C20 1.3816(15) . ?
N8 H8 0.8799 . ?
C1 C22 1.3978(14) . ?
C1 C25 1.4111(16) . ?
C1 C16 1.4923(14) . ?
C2 C3 1.3944(14) . ?
C2 C7 1.4142(15) . ?
C3 C4 1.3862(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.3987(17) . ?
C4 H4A 0.9300 . ?
C5 C6 1.3882(15) . ?
C5 H5 0.9300 . ?
C6 C7 1.3949(15) . ?
C6 H6A 0.9300 . ?
C7 C8 1.4428(14) . ?
C8 C19 1.3993(14) . ?
C8 C9 1.4049(16) . ?
C9 C18 1.3925(15) . ?
C10 C15 1.3922(15) . ?
C10 C11 1.3923(16) . ?
C11 C12 1.3872(17) . ?
C11 H11A 0.9300 . ?
C12 C13 1.3862(18) . ?
C12 H12 0.9300 . ?
C13 C14 1.3854(18) . ?
C13 H13 0.9300 . ?
C14 C15 1.3862(16) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C19 1.3934(15) . ?
C16 C17 1.4137(16) . ?
C17 C18 1.3841(15) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C24 1.3953(15) . ?
C20 C21 1.4104(15) . ?
C21 C29 1.3964(15) . ?
C21 C23 1.4483(14) . ?
C22 C23 1.3999(14) . ?
C22 H22 0.9300 . ?
C23 C27 1.4087(16) . ?
C24 C28 1.3836(17) . ?
C24 H24 0.9300 . ?
C25 C26 1.3813(15) . ?
C25 H25 0.9300 . ?
C26 C27 1.3940(15) . ?
C26 H26 0.9300 . ?
C28 C30 1.4052(17) . ?
C28 H28 0.9300 . ?
C29 C30 1.3885(15) . ?
C29 H29 0.9300 . ?
C30 H30 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
C2 N1 C9 107.97(9) . . ?
C2 N1 C10 125.50(9) . . ?
C9 N1 C10 125.90(9) . . ?
C27 N8 C20 109.13(9) . . ?
C27 N8 H8 125.5 . . ?
C20 N8 H8 125.4 . . ?
C22 C1 C25 118.39(10) . . ?
C22 C1 C16 121.69(10) . . ?
C25 C1 C16 119.92(10) . . ?
C3 C2 N1 129.78(10) . . ?
C3 C2 C7 121.08(10) . . ?
N1 C2 C7 109.00(9) . . ?
C4 C3 C2 117.60(10) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C5 122.08(10) . . ?
C3 C4 H4A 119.0 . . ?
C5 C4 H4A 119.0 . . ?
C6 C5 C4 120.21(10) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 118.93(10) . . ?
C5 C6 H6A 120.5 . . ?
C7 C6 H6A 120.5 . . ?
C6 C7 C2 120.09(9) . . ?
C6 C7 C8 132.92(10) . . ?
C2 C7 C8 106.74(9) . . ?
C19 C8 C9 120.45(10) . . ?
C19 C8 C7 132.46(10) . . ?
C9 C8 C7 107.07(9) . . ?
C18 C9 N1 130.20(11) . . ?
C18 C9 C8 120.56(10) . . ?
N1 C9 C8 109.22(9) . . ?
C15 C10 C11 119.62(10) . . ?
C15 C10 N1 120.10(10) . . ?
C11 C10 N1 120.28(10) . . ?
C12 C11 C10 119.99(11) . . ?
C12 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
C13 C12 C11 120.30(11) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 119.66(11) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.45(11) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 119.93(11) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
C19 C16 C17 117.93(10) . . ?
C19 C16 C1 120.91(10) . . ?
C17 C16 C1 121.17(10) . . ?
C18 C17 C16 123.05(10) . . ?
C18 C17 H17 118.5 . . ?
C16 C17 H17 118.5 . . ?
C17 C18 C9 117.91(11) . . ?
C17 C18 H18 121.0 . . ?
C9 C18 H18 121.0 . . ?
C16 C19 C8 119.96(10) . . ?
C16 C19 H19 120.0 . . ?
C8 C19 H19 120.0 . . ?
N8 C20 C24 129.20(11) . . ?
N8 C20 C21 108.86(9) . . ?
C24 C20 C21 121.94(10) . . ?
C29 C21 C20 119.48(9) . . ?
C29 C21 C23 134.01(10) . . ?
C20 C21 C23 106.51(9) . . ?
C1 C22 C23 119.82(10) . . ?
C1 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C22 C23 C27 119.84(10) . . ?
C22 C23 C21 133.56(10) . . ?
C27 C23 C21 106.58(9) . . ?
C28 C24 C20 117.43(10) . . ?
C28 C24 H24 121.3 . . ?
C20 C24 H24 121.3 . . ?
C26 C25 C1 123.07(10) . . ?
C26 C25 H25 118.5 . . ?
C1 C25 H25 118.5 . . ?
C25 C26 C27 117.52(10) . . ?
C25 C26 H26 121.2 . . ?
C27 C26 H26 121.2 . . ?
N8 C27 C26 129.74(11) . . ?
N8 C27 C23 108.92(9) . . ?
C26 C27 C23 121.34(10) . . ?
C24 C28 C30 121.64(10) . . ?
C24 C28 H28 119.2 . . ?
C30 C28 H28 119.2 . . ?
C30 C29 C21 119.01(10) . . ?
C30 C29 H29 120.5 . . ?
C21 C29 H29 120.5 . . ?
C29 C30 C28 120.51(11) . . ?
C29 C30 H30 119.7 . . ?
C28 C30 H30 119.7 . . ?

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
C9 N1 C2 C3 -174.73(12) . . . . ?
C10 N1 C2 C3 -3.42(19) . . . . ?
C9 N1 C2 C7 0.89(12) . . . . ?
C10 N1 C2 C7 172.21(10) . . . . ?
N1 C2 C3 C4 175.76(11) . . . . ?
C7 C2 C3 C4 0.59(17) . . . . ?
C2 C3 C4 C5 -1.12(18) . . . . ?
C3 C4 C5 C6 0.51(19) . . . . ?
C4 C5 C6 C7 0.67(17) . . . . ?
C5 C6 C7 C2 -1.18(16) . . . . ?
C5 C6 C7 C8 -174.53(11) . . . . ?
C3 C2 C7 C6 0.56(16) . . . . ?
N1 C2 C7 C6 -175.52(10) . . . . ?
C3 C2 C7 C8 175.48(10) . . . . ?
N1 C2 C7 C8 -0.60(12) . . . . ?
C6 C7 C8 C19 -4.3(2) . . . . ?
C2 C7 C8 C19 -178.33(12) . . . . ?
C6 C7 C8 C9 174.07(12) . . . . ?
C2 C7 C8 C9 0.08(12) . . . . ?
C2 N1 C9 C18 -179.35(12) . . . . ?
C10 N1 C9 C18 9.4(2) . . . . ?
C2 N1 C9 C8 -0.84(13) . . . . ?
C10 N1 C9 C8 -172.11(10) . . . . ?
C19 C8 C9 C18 -2.22(17) . . . . ?
C7 C8 C9 C18 179.15(10) . . . . ?
C19 C8 C9 N1 179.10(10) . . . . ?
C7 C8 C9 N1 0.47(13) . . . . ?
C2 N1 C10 C15 50.70(15) . . . . ?
C9 N1 C10 C15 -139.51(11) . . . . ?
C2 N1 C10 C11 -128.55(12) . . . . ?
C9 N1 C10 C11 41.24(16) . . . . ?
C15 C10 C11 C12 1.54(16) . . . . ?
N1 C10 C11 C12 -179.21(10) . . . . ?
C10 C11 C12 C13 -2.63(17) . . . . ?
C11 C12 C13 C14 1.78(18) . . . . ?
C12 C13 C14 C15 0.15(18) . . . . ?
C13 C14 C15 C10 -1.23(17) . . . . ?
C11 C10 C15 C14 0.38(16) . . . . ?
N1 C10 C15 C14 -178.88(10) . . . . ?
C22 C1 C16 C19 -161.41(10) . . . . ?
C25 C1 C16 C19 19.28(16) . . . . ?
C22 C1 C16 C17 18.53(16) . . . . ?
C25 C1 C16 C17 -160.77(11) . . . . ?
C19 C16 C17 C18 -2.64(18) . . . . ?
C1 C16 C17 C18 177.41(11) . . . . ?
C16 C17 C18 C9 -0.73(18) . . . . ?
N1 C9 C18 C17 -178.48(11) . . . . ?
C8 C9 C18 C17 3.16(18) . . . . ?
C17 C16 C19 C8 3.58(17) . . . . ?
C1 C16 C19 C8 -176.47(10) . . . . ?
C9 C8 C19 C16 -1.27(17) . . . . ?
C7 C8 C19 C16 176.96(11) . . . . ?
C27 N8 C20 C24 179.54(11) . . . . ?
C27 N8 C20 C21 -0.37(13) . . . . ?
N8 C20 C21 C29 179.91(10) . . . . ?
C24 C20 C21 C29 -0.01(17) . . . . ?
N8 C20 C21 C23 0.21(12) . . . . ?
C24 C20 C21 C23 -179.71(10) . . . . ?
C25 C1 C22 C23 -0.48(15) . . . . ?
C16 C1 C22 C23 -179.80(9) . . . . ?
C1 C22 C23 C27 -0.84(15) . . . . ?
C1 C22 C23 C21 -178.85(11) . . . . ?
C29 C21 C23 C22 -1.4(2) . . . . ?
C20 C21 C23 C22 178.21(11) . . . . ?
C29 C21 C23 C27 -179.62(12) . . . . ?
C20 C21 C23 C27 0.02(12) . . . . ?
N8 C20 C24 C28 -179.97(12) . . . . ?
C21 C20 C24 C28 -0.07(17) . . . . ?
C22 C1 C25 C26 1.86(17) . . . . ?
C16 C1 C25 C26 -178.82(10) . . . . ?
C1 C25 C26 C27 -1.78(17) . . . . ?
C20 N8 C27 C26 -179.23(12) . . . . ?
C20 N8 C27 C23 0.38(13) . . . . ?
C25 C26 C27 N8 179.94(11) . . . . ?
C25 C26 C27 C23 0.37(17) . . . . ?
C22 C23 C27 N8 -178.73(9) . . . . ?
C21 C23 C27 N8 -0.24(12) . . . . ?
C22 C23 C27 C26 0.92(16) . . . . ?
C21 C23 C27 C26 179.41(10) . . . . ?
C20 C24 C28 C30 0.01(18) . . . . ?
C20 C21 C29 C30 0.14(16) . . . . ?
C23 C21 C29 C30 179.74(11) . . . . ?
C21 C29 C30 C28 -0.19(17) . . . . ?
C24 C28 C30 C29 0.12(18) . . . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_20240819-67338-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2409052'
loop_
_audit_author_name
_audit_author_address
'Jiajun Du'
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2024-12-10 deposited with the CCDC.	2025-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 N'
_chemical_formula_sum            'C18 H13 N'
_chemical_formula_weight         243.29

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.4624(5)
_cell_length_b                   7.3908(5)
_cell_length_c                   13.2977(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.493(8)
_cell_angle_gamma                90
_cell_volume                     622.39(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    3452
_cell_measurement_theta_min      3.3600
_cell_measurement_theta_max      73.9520

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.578
_shelx_estimated_absorpt_T_min   0.903
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.68198
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix-Arc 150'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5112
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.392
_diffrn_reflns_theta_max         76.602
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.712
_diffrn_reflns_point_group_measured_fraction_full 0.755
_reflns_number_total             1869
_reflns_number_gt                1584
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.365
_reflns_Friedel_fraction_max     0.414
_reflns_Friedel_fraction_full    0.471

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0770P)²+0.1156P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(16)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1869
_refine_ls_number_parameters     174
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1293
_refine_ls_wR_factor_gt          0.1050
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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_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
C3 C 0.4429(7) 0.4429(6) 0.2337(3) 0.0697(10) Uani 1 1 d . . . . .
H3 H 0.385266 0.433188 0.163988 0.084 Uiso 1 1 calc R U . . .
C6 C 0.6078(4) 0.4742(4) 0.4419(2) 0.0473(7) Uani 1 1 d . . . . .
C7 C 0.7406(4) 0.4699(4) 0.5433(2) 0.0466(7) Uani 1 1 d . . . . .
C8 C 0.7086(4) 0.5186(5) 0.6404(2) 0.0484(7) Uani 1 1 d . . . . .
H8 H 0.580745 0.569034 0.648075 0.058 Uiso 1 1 calc R U . . .
C9 C 0.8692(4) 0.4913(4) 0.7257(2) 0.0508(8) Uani 1 1 d . . . . .
C10 C 1.0610(5) 0.4180(5) 0.7117(3) 0.0585(9) Uani 1 1 d . . . . .
H10 H 1.168616 0.401759 0.768833 0.070 Uiso 1 1 calc R U . . .
C11 C 1.0971(5) 0.3689(5) 0.6168(3) 0.0613(9) Uani 1 1 d . . . . .
H11 H 1.226010 0.320367 0.609357 0.074 Uiso 1 1 calc R U . . .
C12 C 0.9345(5) 0.3943(5) 0.5330(3) 0.0527(8) Uani 1 1 d . . . . .
C13 C 0.8335(5) 0.5306(5) 0.8307(2) 0.0525(8) Uani 1 1 d . . . . .
C14 C 0.6468(5) 0.4813(6) 0.8585(3) 0.0607(9) Uani 1 1 d . . . . .
H14 H 0.542164 0.425168 0.810492 0.073 Uiso 1 1 calc R U . . .
C15 C 0.6121(6) 0.5133(7) 0.9560(3) 0.0718(11) Uani 1 1 d . . . . .
H15 H 0.484928 0.479433 0.973191 0.086 Uiso 1 1 calc R U . . .
C16 C 0.7669(7) 0.5960(6) 1.0280(3) 0.0741(11) Uani 1 1 d . . . . .
H16 H 0.743966 0.618793 1.093663 0.089 Uiso 1 1 calc R U . . .
C17 C 0.9539(7) 0.6441(6) 1.0024(3) 0.0735(12) Uani 1 1 d . . . . .
H17 H 1.058774 0.698666 1.050951 0.088 Uiso 1 1 calc R U . . .
C18 C 0.9879(6) 0.6121(5) 0.9047(3) 0.0643(9) Uani 1 1 d . . . . .
H18 H 1.115808 0.645411 0.888149 0.077 Uiso 1 1 calc R U . . .
C4 C 0.3222(6) 0.5159(5) 0.2990(3) 0.0630(9) Uani 1 1 d . . . . .
H4 H 0.185177 0.554431 0.272524 0.076 Uiso 1 1 calc R U . . .
C5 C 0.4027(5) 0.5321(5) 0.4029(2) 0.0532(8) Uani 1 1 d . . . . .
H5 H 0.320743 0.580997 0.446260 0.064 Uiso 1 1 calc R U . . .
C2 C 0.6476(6) 0.3844(6) 0.2703(3) 0.0662(10) Uani 1 1 d . . . . .
H2 H 0.728405 0.336007 0.226242 0.079 Uiso 1 1 calc R U . . .
N1 N 0.9240(4) 0.3539(5) 0.4307(2) 0.0609(8) Uani 1 1 d . . . . .
H1 H 1.024555 0.306897 0.405670 0.073 Uiso 1 1 calc R U . . .
C1 C 0.7283(5) 0.4001(5) 0.3748(3) 0.0529(8) 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
C3 C2 1.385(5) . ?
C3 C4 1.388(5) . ?
C6 C5 1.391(4) . ?
C6 C1 1.408(4) . ?
C6 C7 1.447(4) . ?
C7 C8 1.395(4) . ?
C7 C12 1.404(4) . ?
C8 C9 1.391(4) . ?
C9 C10 1.399(4) . ?
C9 C13 1.488(4) . ?
C10 C11 1.376(5) . ?
C11 C12 1.384(5) . ?
C12 N1 1.382(4) . ?
C13 C14 1.379(4) . ?
C13 C18 1.391(5) . ?
C14 C15 1.380(5) . ?
C15 C16 1.382(6) . ?
C16 C17 1.366(6) . ?
C17 C18 1.380(5) . ?
C4 C5 1.381(5) . ?
C2 C1 1.389(5) . ?
N1 C1 1.376(5) . ?

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
C2 C3 C4 121.2(4) . . ?
C5 C6 C1 119.3(3) . . ?
C5 C6 C7 134.3(3) . . ?
C1 C6 C7 106.4(3) . . ?
C8 C7 C12 119.5(3) . . ?
C8 C7 C6 133.4(3) . . ?
C12 C7 C6 107.0(3) . . ?
C9 C8 C7 119.5(3) . . ?
C8 C9 C10 119.0(3) . . ?
C8 C9 C13 120.4(3) . . ?
C10 C9 C13 120.5(3) . . ?
C11 C10 C9 122.8(3) . . ?
C10 C11 C12 117.5(3) . . ?
N1 C12 C11 130.1(3) . . ?
N1 C12 C7 108.2(3) . . ?
C11 C12 C7 121.7(3) . . ?
C14 C13 C18 117.8(3) . . ?
C14 C13 C9 120.5(3) . . ?
C18 C13 C9 121.7(3) . . ?
C13 C14 C15 121.4(3) . . ?
C14 C15 C16 119.7(3) . . ?
C17 C16 C15 119.8(4) . . ?
C16 C17 C18 120.3(4) . . ?
C17 C18 C13 120.9(3) . . ?
C5 C4 C3 120.9(4) . . ?
C4 C5 C6 119.2(3) . . ?
C3 C2 C1 117.9(3) . . ?
C1 N1 C12 109.8(3) . . ?
N1 C1 C2 129.9(3) . . ?
N1 C1 C6 108.6(3) . . ?
C2 C1 C6 121.5(3) . . ?

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
C5 C6 C7 C8 2.0(6) . . . . ?
C1 C6 C7 C8 -177.7(3) . . . . ?
C5 C6 C7 C12 179.9(4) . . . . ?
C1 C6 C7 C12 0.1(3) . . . . ?
C12 C7 C8 C9 -0.1(5) . . . . ?
C6 C7 C8 C9 177.6(3) . . . . ?
C7 C8 C9 C10 1.1(5) . . . . ?
C7 C8 C9 C13 -175.9(3) . . . . ?
C8 C9 C10 C11 -1.0(5) . . . . ?
C13 C9 C10 C11 175.9(3) . . . . ?
C9 C10 C11 C12 0.0(5) . . . . ?
C10 C11 C12 N1 -178.2(3) . . . . ?
C10 C11 C12 C7 1.0(5) . . . . ?
C8 C7 C12 N1 178.4(3) . . . . ?
C6 C7 C12 N1 0.2(3) . . . . ?
C8 C7 C12 C11 -0.9(5) . . . . ?
C6 C7 C12 C11 -179.2(3) . . . . ?
C8 C9 C13 C14 42.3(5) . . . . ?
C10 C9 C13 C14 -134.6(3) . . . . ?
C8 C9 C13 C18 -139.9(4) . . . . ?
C10 C9 C13 C18 43.2(5) . . . . ?
C18 C13 C14 C15 0.8(6) . . . . ?
C9 C13 C14 C15 178.8(3) . . . . ?
C13 C14 C15 C16 -0.2(6) . . . . ?
C14 C15 C16 C17 -0.5(7) . . . . ?
C15 C16 C17 C18 0.6(7) . . . . ?
C16 C17 C18 C13 0.0(6) . . . . ?
C14 C13 C18 C17 -0.7(6) . . . . ?
C9 C13 C18 C17 -178.6(4) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C1 C6 C5 C4 -0.2(5) . . . . ?
C7 C6 C5 C4 -179.9(3) . . . . ?
C4 C3 C2 C1 0.3(6) . . . . ?
C11 C12 N1 C1 178.8(4) . . . . ?
C7 C12 N1 C1 -0.4(4) . . . . ?
C12 N1 C1 C2 179.9(4) . . . . ?
C12 N1 C1 C6 0.5(4) . . . . ?
C3 C2 C1 N1 -179.7(4) . . . . ?
C3 C2 C1 C6 -0.4(5) . . . . ?
C5 C6 C1 N1 179.8(3) . . . . ?
C7 C6 C1 N1 -0.4(4) . . . . ?
C5 C6 C1 C2 0.4(5) . . . . ?
C7 C6 C1 C2 -179.8(3) . . . . ?

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.046

