# Electronic Supplementary Material (ESI) for Molecular Systems Design & Engineering.
# This journal is © The Royal Society of Chemistry 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_1293Ex_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2090427'
loop_
_audit_author_name
_audit_author_address
'SUVENDU MAITY'
;Jadavpur University
India
;
_audit_update_record             
;
2021-06-16 deposited with the CCDC.	2021-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H24 N2'
_chemical_formula_sum            'C40 H24 N2'
_chemical_formula_weight         532.61

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.1071(5)
_cell_length_b                   14.3548(6)
_cell_length_c                   15.1617(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2635.03(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7221
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      24.27

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             1166
_exptl_transmission_factor_min   0.791
_exptl_transmission_factor_max   0.867
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Mo
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39914
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_av_R_equivalents  0.0969
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.578
_diffrn_reflns_theta_max         28.289
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3251
_reflns_number_gt                1705
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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+0.4267P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3251
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1630
_refine_ls_R_factor_gt           0.0768
_refine_ls_wR_factor_ref         0.2197
_refine_ls_wR_factor_gt          0.1666
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_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
N1 N 0.42601(19) 0.50927(16) 0.82403(14) 0.0499(6) Uani 1 1 d . . . . .
C18 C 0.4658(2) 0.50636(19) 0.91231(16) 0.0417(7) Uani 1 1 d . . . . .
C15 C 0.5103(2) 0.60934(17) 0.61301(15) 0.0363(6) Uani 1 1 d . . . . .
C1 C 0.4761(2) 0.56076(18) 0.76964(16) 0.0456(7) Uani 1 1 d . . . . .
H1 H 0.538403 0.593046 0.788384 0.055 Uiso 1 1 calc R U . . .
C19 C 0.4900(2) 0.58600(19) 0.96048(18) 0.0464(7) Uani 1 1 d . . . . .
H19 H 0.482635 0.644238 0.934257 0.056 Uiso 1 1 calc R U . . .
C20 C 0.4752(2) 0.42036(19) 0.95356(17) 0.0472(7) Uani 1 1 d . . . . .
H20 H 0.457828 0.366419 0.922561 0.057 Uiso 1 1 calc R U . . .
C2 C 0.4393(2) 0.57161(17) 0.67735(16) 0.0408(7) Uani 1 1 d . . . . .
C16 C 0.4722(2) 0.61693(16) 0.52412(16) 0.0379(6) Uani 1 1 d . . . . .
C17 C 0.5433(2) 0.65304(16) 0.45722(16) 0.0401(6) Uani 1 1 d . . . . .
C14 C 0.6225(2) 0.63751(19) 0.63059(16) 0.0465(7) Uani 1 1 d . . . . .
H14 H 0.649795 0.632158 0.687693 0.056 Uiso 1 1 calc R U . . .
C12 C 0.6526(2) 0.68079(17) 0.47805(17) 0.0440(7) Uani 1 1 d . . . . .
C3 C 0.3335(2) 0.54217(19) 0.65326(17) 0.0466(7) Uani 1 1 d . . . . .
H3 H 0.286920 0.517251 0.695961 0.056 Uiso 1 1 calc R U . . .
C5 C 0.3639(2) 0.58681(17) 0.50171(16) 0.0414(7) Uani 1 1 d . . . . .
C8 C 0.5057(3) 0.65958(18) 0.36834(17) 0.0467(7) Uani 1 1 d . . . . .
C13 C 0.6890(2) 0.67138(19) 0.56687(18) 0.0495(7) Uani 1 1 d . . . . .
H13 H 0.760678 0.689065 0.581361 0.059 Uiso 1 1 calc R U . . .
C4 C 0.2969(2) 0.54931(19) 0.56778(18) 0.0483(7) Uani 1 1 d . . . . .
H4 H 0.226250 0.528796 0.553615 0.058 Uiso 1 1 calc R U . . .
C9 C 0.5775(3) 0.6933(2) 0.30431(18) 0.0593(9) Uani 1 1 d . . . . .
H9 H 0.553614 0.698175 0.246192 0.071 Uiso 1 1 calc R U . . .
C10 C 0.6838(3) 0.7196(2) 0.3258(2) 0.0637(9) Uani 1 1 d . . . . .
H10 H 0.730637 0.741862 0.282012 0.076 Uiso 1 1 calc R U . . .
C6 C 0.3288(3) 0.5946(2) 0.41154(19) 0.0525(8) Uani 1 1 d . . . . .
H6 H 0.258115 0.575197 0.396065 0.063 Uiso 1 1 calc R U . . .
C7 C 0.3959(3) 0.6293(2) 0.34906(18) 0.0571(8) Uani 1 1 d . . . . .
H7 H 0.370078 0.633658 0.291446 0.069 Uiso 1 1 calc R U . . .
C11 C 0.7211(3) 0.7134(2) 0.41047(19) 0.0565(8) Uani 1 1 d . . . . .
H11 H 0.793138 0.731207 0.423480 0.068 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 C1 1.262(3) . ?
N1 C18 1.423(3) . ?
C18 C19 1.388(4) . ?
C18 C20 1.389(4) . ?
C15 C2 1.408(3) . ?
C15 C16 1.428(3) . ?
C15 C14 1.442(4) . ?
C1 C2 1.477(3) . ?
C1 H1 0.9300 . ?
C19 C20 1.373(4) 5_667 ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C2 C3 1.397(4) . ?
C16 C5 1.422(4) . ?
C16 C17 1.428(4) . ?
C17 C12 1.418(4) . ?
C17 C8 1.425(3) . ?
C14 C13 1.349(3) . ?
C14 H14 0.9300 . ?
C12 C11 1.399(4) . ?
C12 C13 1.423(4) . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C5 C4 1.397(4) . ?
C5 C6 1.436(3) . ?
C8 C9 1.390(4) . ?
C8 C7 1.429(4) . ?
C13 H13 0.9300 . ?
C4 H4 0.9300 . ?
C9 C10 1.381(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.363(4) . ?
C10 H10 0.9300 . ?
C6 C7 1.343(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C11 H11 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
C1 N1 C18 118.0(2) . . ?
C19 C18 C20 118.5(2) . . ?
C19 C18 N1 122.8(2) . . ?
C20 C18 N1 118.5(2) . . ?
C2 C15 C16 119.1(2) . . ?
C2 C15 C14 123.7(2) . . ?
C16 C15 C14 117.2(2) . . ?
N1 C1 C2 122.4(3) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C20 C19 C18 120.6(3) 5_667 . ?
C20 C19 H19 119.7 5_667 . ?
C18 C19 H19 119.7 . . ?
C19 C20 C18 120.8(2) 5_667 . ?
C19 C20 H20 119.6 5_667 . ?
C18 C20 H20 119.6 . . ?
C3 C2 C15 119.6(2) . . ?
C3 C2 C1 119.5(2) . . ?
C15 C2 C1 120.9(2) . . ?
C5 C16 C17 119.8(2) . . ?
C5 C16 C15 120.0(2) . . ?
C17 C16 C15 120.3(2) . . ?
C12 C17 C8 119.3(3) . . ?
C12 C17 C16 120.4(2) . . ?
C8 C17 C16 120.2(3) . . ?
C13 C14 C15 122.1(2) . . ?
C13 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C11 C12 C17 119.0(3) . . ?
C11 C12 C13 122.8(3) . . ?
C17 C12 C13 118.2(2) . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.4 . . ?
C4 C5 C16 118.8(2) . . ?
C4 C5 C6 122.7(3) . . ?
C16 C5 C6 118.5(3) . . ?
C9 C8 C17 118.9(3) . . ?
C9 C8 C7 123.0(3) . . ?
C17 C8 C7 118.0(3) . . ?
C14 C13 C12 121.8(3) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C3 C4 C5 121.2(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C7 C6 C5 121.4(3) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 122.1(3) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C10 C11 C12 121.0(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.136



