# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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. 
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data_tx10889_pl_sq
_database_code_depnum_ccdc_archive 'CCDC 2257690'
loop_
_audit_author_name
_audit_author_address
Meng
;RENMIN UNIVERSITY of CHINA
China
;
_audit_update_record             
;
2023-04-20 deposited with the CCDC.	2024-10-17 downloaded from the CCDC.
;
_audit_creation_date             2023-01-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C46 H32 N4'
_chemical_formula_sum            'C46 H32 N4'
_chemical_formula_weight         640.75
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   16.6067(7)
_cell_length_b                   5.4254(3)
_cell_length_c                   20.6546(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.326(4)
_cell_angle_gamma                90
_cell_volume                     1857.80(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5130
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      76.1500
_cell_measurement_theta_min      3.2960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             672
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            3686
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.683
_diffrn_reflns_theta_min         3.322
_diffrn_ambient_temperature      170.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                2436
_reflns_number_total             3686
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -1.3(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3686
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0740
_refine_ls_restrained_S_all      1.066
_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)+(0.1567P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2158
_refine_ls_wR_factor_ref         0.2447
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 2.3(17)
 -1.3(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C005(H005), C006(H006), C007(H007), C009(H009), C00C(H00C), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
N002 N 0.1963(3) 0.9596(11) -0.0837(2) 0.0874(14) Uani 1 1 d . . . . .
N004 N 0.4404(4) 1.0248(13) -0.7389(3) 0.1090(19) Uani 1 1 d . . . . .
C001 C 0.1169(2) 0.9762(9) -0.2863(2) 0.0616(11) Uani 1 1 d . . . . .
C003 C 0.0662(2) 0.9856(9) -0.4191(2) 0.0622(11) Uani 1 1 d . . . . .
C005 C 0.2315(3) 1.1669(11) -0.5659(2) 0.0717(13) Uani 1 1 d . . . . .
H005 H 0.271847 1.289763 -0.558887 0.086 Uiso 1 1 calc R . . . .
C006 C 0.1408(3) 0.7955(10) -0.3288(3) 0.0723(14) Uani 1 1 d . . . . .
H006 H 0.173662 0.663313 -0.312590 0.087 Uiso 1 1 calc R . . . .
C007 C 0.0676(3) 1.1646(9) -0.3119(3) 0.0670(12) Uani 1 1 d . . . . .
H007 H 0.050743 1.292292 -0.284236 0.080 Uiso 1 1 calc R . . . .
C008 C 0.1067(2) 0.9821(10) -0.5343(3) 0.0654(11) Uani 1 1 d . . . . .
C009 C 0.0428(3) 1.1681(10) -0.3770(2) 0.0647(11) Uani 1 1 d . . . . .
H009 H 0.009050 1.298151 -0.393278 0.078 Uiso 1 1 calc R . . . .
C00A C 0.1428(2) 0.9697(9) -0.2171(2) 0.0650(12) Uani 1 1 d . . . . .
C00B C 0.2377(2) 1.0005(10) -0.6161(2) 0.0672(13) Uani 1 1 d . . . . .
C00C C 0.1681(3) 1.1580(10) -0.5261(3) 0.0696(13) Uani 1 1 d . . . . .
H00C H 0.165913 1.274599 -0.491888 0.084 Uiso 1 1 calc R . . . .
C00D C 0.0394(3) 0.9814(9) -0.4895(3) 0.0648(11) Uani 1 1 d . . . . .
C00E C 0.3056(3) 1.0086(12) -0.6595(3) 0.0746(14) Uani 1 1 d . . . . .
C00F C 0.1179(3) 0.8045(10) -0.3937(3) 0.0713(13) Uani 1 1 d . . . . .
H00F H 0.137848 0.683620 -0.421921 0.086 Uiso 1 1 calc R . . . .
C00G C 0.3860(4) 0.8617(17) -0.7431(3) 0.097(2) Uani 1 1 d . . . . .
H00G H 0.391303 0.738879 -0.775315 0.117 Uiso 1 1 calc R . . . .
C00H C 0.1133(3) 0.8147(11) -0.5841(3) 0.0843(18) Uani 1 1 d . . . . .
H00H H 0.072925 0.692082 -0.591294 0.101 Uiso 1 1 calc R . . . .
C00I C 0.2156(4) 0.7897(13) -0.1246(4) 0.0951(19) Uani 1 1 d . . . . .
H00I H 0.249243 0.659222 -0.108460 0.114 Uiso 1 1 calc R . . . .
C00J C 0.3193(3) 0.8422(16) -0.7057(3) 0.094(2) Uani 1 1 d . . . . .
H00J H 0.282770 0.708871 -0.712968 0.112 Uiso 1 1 calc R . . . .
C00K C 0.1911(4) 0.7847(12) -0.1890(3) 0.0851(16) Uani 1 1 d . . . . .
H00K H 0.207374 0.651631 -0.215106 0.102 Uiso 1 1 calc R . . . .
C00L C 0.1772(3) 0.8224(12) -0.6233(3) 0.0881(19) Uani 1 1 d . . . . .
H00L H 0.180350 0.702266 -0.656497 0.106 Uiso 1 1 calc R . . . .
C00M C 0.1243(5) 1.1535(14) -0.1735(3) 0.100(2) Uani 1 1 d . . . . .
H00M H 0.092078 1.289486 -0.188125 0.120 Uiso 1 1 calc R . . . .
C00N C 0.1521(5) 1.1411(14) -0.1095(4) 0.109(2) Uani 1 1 d . . . . .
H00N H 0.138431 1.272659 -0.081798 0.130 Uiso 1 1 calc R . . . .
C00O C 0.3575(4) 1.2046(15) -0.6628(4) 0.100(2) Uani 1 1 d . . . . .
H00O H 0.348705 1.346228 -0.637131 0.120 Uiso 1 1 calc R . . . .
C00P C 0.4222(5) 1.2037(18) -0.7020(3) 0.109(2) Uani 1 1 d . . . . .
H00P H 0.455464 1.346147 -0.701639 0.130 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
N002 C00I 1.302(9) . ?
N002 C00N 1.322(9) . ?
N004 C00G 1.264(10) . ?
N004 C00P 1.280(10) . ?
C001 C006 1.388(7) . ?
C001 C007 1.394(7) . ?
C001 C00A 1.470(7) . ?
C003 C009 1.388(7) . ?
C003 C00D 1.497(7) . ?
C003 C00F 1.387(7) . ?
C005 H005 0.9500 . ?
C005 C00B 1.383(6) . ?
C005 C00C 1.375(7) . ?
C006 H006 0.9500 . ?
C006 C00F 1.374(8) . ?
C007 H007 0.9500 . ?
C007 C009 1.384(7) . ?
C008 C00C 1.400(6) . ?
C008 C00D 1.492(6) . ?
C008 C00H 1.381(7) . ?
C009 H009 0.9500 . ?
C00A C00K 1.390(7) . ?
C00A C00M 1.389(9) . ?
C00B C00E 1.481(6) . ?
C00B C00L 1.396(7) . ?
C00C H00C 0.9500 . ?
C00D C00D 1.355(9) 2_554 ?
C00E C00J 1.343(8) . ?
C00E C00O 1.373(10) . ?
C00F H00F 0.9500 . ?
C00G H00G 0.9500 . ?
C00G C00J 1.391(9) . ?
C00H H00H 0.9500 . ?
C00H C00L 1.372(8) . ?
C00I H00I 0.9500 . ?
C00I C00K 1.369(9) . ?
C00J H00J 0.9500 . ?
C00K H00K 0.9500 . ?
C00L H00L 0.9500 . ?
C00M H00M 0.9500 . ?
C00M C00N 1.377(10) . ?
C00N H00N 0.9500 . ?
C00O H00O 0.9500 . ?
C00O C00P 1.382(9) . ?
C00P H00P 0.9500 . ?

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
C00I N002 C00N 114.7(6) . . ?
C00G N004 C00P 112.3(6) . . ?
C006 C001 C007 117.5(5) . . ?
C006 C001 C00A 121.2(4) . . ?
C007 C001 C00A 121.2(4) . . ?
C009 C003 C00D 122.7(4) . . ?
C00F C003 C009 117.3(5) . . ?
C00F C003 C00D 119.9(4) . . ?
C00B C005 H005 119.4 . . ?
C00C C005 H005 119.4 . . ?
C00C C005 C00B 121.2(4) . . ?
C001 C006 H006 119.4 . . ?
C00F C006 C001 121.2(4) . . ?
C00F C006 H006 119.4 . . ?
C001 C007 H007 119.6 . . ?
C009 C007 C001 120.9(5) . . ?
C009 C007 H007 119.6 . . ?
C00C C008 C00D 119.5(4) . . ?
C00H C008 C00C 116.8(4) . . ?
C00H C008 C00D 123.7(4) . . ?
C003 C009 H009 119.3 . . ?
C007 C009 C003 121.4(4) . . ?
C007 C009 H009 119.3 . . ?
C00K C00A C001 123.6(5) . . ?
C00M C00A C001 123.3(4) . . ?
C00M C00A C00K 113.1(5) . . ?
C005 C00B C00E 121.7(4) . . ?
C005 C00B C00L 116.6(4) . . ?
C00L C00B C00E 121.7(4) . . ?
C005 C00C C008 121.9(4) . . ?
C005 C00C H00C 119.0 . . ?
C008 C00C H00C 119.0 . . ?
C008 C00D C003 114.3(4) . . ?
C00D C00D C003 122.6(5) 2_554 . ?
C00D C00D C008 123.1(6) 2_554 . ?
C00J C00E C00B 125.2(5) . . ?
C00J C00E C00O 110.6(5) . . ?
C00O C00E C00B 123.8(5) . . ?
C003 C00F H00F 119.2 . . ?
C006 C00F C003 121.6(5) . . ?
C006 C00F H00F 119.2 . . ?
N004 C00G H00G 116.4 . . ?
N004 C00G C00J 127.2(7) . . ?
C00J C00G H00G 116.4 . . ?
C008 C00H H00H 119.5 . . ?
C00L C00H C008 121.1(5) . . ?
C00L C00H H00H 119.5 . . ?
N002 C00I H00I 117.5 . . ?
N002 C00I C00K 125.0(6) . . ?
C00K C00I H00I 117.5 . . ?
C00E C00J C00G 121.1(7) . . ?
C00E C00J H00J 119.5 . . ?
C00G C00J H00J 119.5 . . ?
C00A C00K H00K 119.2 . . ?
C00I C00K C00A 121.6(6) . . ?
C00I C00K H00K 119.2 . . ?
C00B C00L H00L 118.8 . . ?
C00H C00L C00B 122.3(5) . . ?
C00H C00L H00L 118.8 . . ?
C00A C00M H00M 119.6 . . ?
C00N C00M C00A 120.8(6) . . ?
C00N C00M H00M 119.6 . . ?
N002 C00N C00M 124.8(7) . . ?
N002 C00N H00N 117.6 . . ?
C00M C00N H00N 117.6 . . ?
C00E C00O H00O 118.7 . . ?
C00E C00O C00P 122.6(7) . . ?
C00P C00O H00O 118.7 . . ?
N004 C00P C00O 124.7(8) . . ?
N004 C00P H00P 117.6 . . ?
C00O C00P H00P 117.6 . . ?

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
N002 C00I C00K C00A 1.1(11) . . . . ?
N004 C00G C00J C00E 1.0(12) . . . . ?
C001 C006 C00F C003 -3.8(8) . . . . ?
C001 C007 C009 C003 -0.2(7) . . . . ?
C001 C00A C00K C00I 178.2(5) . . . . ?
C001 C00A C00M C00N -178.2(6) . . . . ?
C005 C00B C00E C00J 174.3(6) . . . . ?
C005 C00B C00E C00O -13.9(9) . . . . ?
C005 C00B C00L C00H 1.7(9) . . . . ?
C006 C001 C007 C009 0.9(6) . . . . ?
C006 C001 C00A C00K -1.1(7) . . . . ?
C006 C001 C00A C00M 176.2(6) . . . . ?
C007 C001 C006 C00F 1.1(7) . . . . ?
C007 C001 C00A C00K 179.1(5) . . . . ?
C007 C001 C00A C00M -3.6(7) . . . . ?
C008 C00H C00L C00B -1.3(11) . . . . ?
C009 C003 C00D C008 122.4(5) . . . . ?
C009 C003 C00D C00D -56.5(5) . . . 2_554 ?
C009 C003 C00F C006 4.3(7) . . . . ?
C00A C001 C006 C00F -178.7(4) . . . . ?
C00A C001 C007 C009 -179.4(4) . . . . ?
C00A C00M C00N N002 -0.9(13) . . . . ?
C00B C005 C00C C008 -0.4(9) . . . . ?
C00B C00E C00J C00G -178.3(6) . . . . ?
C00B C00E C00O C00P 177.6(6) . . . . ?
C00C C005 C00B C00E 179.9(5) . . . . ?
C00C C005 C00B C00L -0.9(8) . . . . ?
C00C C008 C00D C003 -50.4(7) . . . . ?
C00C C008 C00D C00D 128.5(4) . . . 2_554 ?
C00C C008 C00H C00L -0.1(10) . . . . ?
C00D C003 C009 C007 178.9(4) . . . . ?
C00D C003 C00F C006 -176.9(4) . . . . ?
C00D C008 C00C C005 180.0(5) . . . . ?
C00D C008 C00H C00L -179.1(6) . . . . ?
C00E C00B C00L C00H -179.0(6) . . . . ?
C00E C00O C00P N004 0.1(13) . . . . ?
C00F C003 C009 C007 -2.3(6) . . . . ?
C00F C003 C00D C008 -56.3(6) . . . . ?
C00F C003 C00D C00D 124.8(3) . . . 2_554 ?
C00G N004 C00P C00O 9.9(12) . . . . ?
C00H C008 C00C C005 0.9(9) . . . . ?
C00H C008 C00D C003 128.6(6) . . . . ?
C00H C008 C00D C00D -52.5(7) . . . 2_554 ?
C00I N002 C00N C00M 2.5(12) . . . . ?
C00J C00E C00O C00P -9.5(10) . . . . ?
C00K C00A C00M C00N -0.7(10) . . . . ?
C00L C00B C00E C00J -4.9(9) . . . . ?
C00L C00B C00E C00O 166.9(6) . . . . ?
C00M C00A C00K C00I 0.7(9) . . . . ?
C00N N002 C00I C00K -2.6(11) . . . . ?
C00O C00E C00J C00G 8.9(9) . . . . ?
C00P N004 C00G C00J -10.6(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 2.3(17)
2 -1.3(17)

