# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_a-TMB_20190712_200K
_database_code_depnum_ccdc_archive 'CCDC 2064280'
loop_
_audit_author_name
_audit_author_address
'Hiroshi Katagiri'
;Yamagata University
Japan
;
_audit_update_record             
;
2021-02-22 deposited with the CCDC.	2021-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C52 H36 N2'
_chemical_formula_sum            'C52 H36 N2'
_chemical_formula_weight         688.83

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'

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

_cell_length_a                   18.0128(10)
_cell_length_b                   27.5447(16)
_cell_length_c                   7.2185(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3581.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200
_cell_measurement_reflns_used    5397
_cell_measurement_theta_min      2.2510
_cell_measurement_theta_max      30.0110

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             1448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55297
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.765
_oxdiff_exptl_absorpt_empirical_full_max 1.715
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;

_diffrn_ambient_temperature      200
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            22438
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.702
_diffrn_reflns_theta_max         26.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3694
_reflns_number_gt                2638
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.843
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXD (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'

_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)+(0.0849P)²+1.1425P] 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_abs_structure_details 
;
 Flack x determined using 900 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.8(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3694
_refine_ls_number_parameters     244
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1668
_refine_ls_wR_factor_gt          0.1495
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.30436(18) 0.62684(11) 0.2790(6) 0.0616(9) Uani 1 1 d . . . . .
C1 C 0.3606(2) 0.59099(13) 0.2797(6) 0.0517(9) Uani 1 1 d . . . . .
C2 C 0.3443(2) 0.54371(14) 0.2279(6) 0.0540(10) Uani 1 1 d . . . . .
H2 H 0.2952 0.5355 0.1915 0.065 Uiso 1 1 calc R U . . .
C3 C 0.3985(2) 0.50869(13) 0.2287(5) 0.0495(9) Uani 1 1 d . . . . .
H3 H 0.3862 0.4766 0.1920 0.059 Uiso 1 1 calc R U . . .
C4 C 0.47121(19) 0.51899(12) 0.2820(5) 0.0448(8) Uani 1 1 d . . . . .
C5 C 0.4864(2) 0.56653(13) 0.3341(5) 0.0491(9) Uani 1 1 d . . . . .
H5 H 0.5354 0.5750 0.3708 0.059 Uiso 1 1 calc R U . . .
C6 C 0.4321(2) 0.60172(14) 0.3338(6) 0.0540(10) Uani 1 1 d . . . . .
H6 H 0.4440 0.6338 0.3715 0.065 Uiso 1 1 calc R U . . .
C7 C 0.2281(3) 0.61433(15) 0.2980(7) 0.0686(12) Uani 1 1 d . . . . .
C8 C 0.1774(3) 0.62557(18) 0.1640(8) 0.0806(15) Uani 1 1 d . . . . .
H8 H 0.1942 0.6417 0.0555 0.097 Uiso 1 1 calc R U . . .
C9 C 0.1043(4) 0.6147(3) 0.1787(13) 0.112(2) Uani 1 1 d . . . . .
H9 H 0.0709 0.6238 0.0832 0.134 Uiso 1 1 calc R U . . .
C10 C 0.0784(4) 0.5901(3) 0.3338(15) 0.124(3) Uani 1 1 d . . . . .
H10 H 0.0275 0.5814 0.3431 0.149 Uiso 1 1 calc R U . . .
C11 C 0.1281(3) 0.5784(2) 0.4764(11) 0.0922(18) Uani 1 1 d . . . . .
C12 C 0.1063(5) 0.5526(3) 0.6380(17) 0.129(3) Uani 1 1 d . . . . .
H12 H 0.0568 0.5410 0.6477 0.154 Uiso 1 1 calc R U . . .
C13 C 0.1549(7) 0.5441(3) 0.7800(14) 0.142(4) Uani 1 1 d . . . . .
H13 H 0.1390 0.5271 0.8875 0.171 Uiso 1 1 calc R U . . .
C14 C 0.2254(5) 0.5599(3) 0.7660(10) 0.117(2) Uani 1 1 d . . . . .
H14 H 0.2580 0.5550 0.8677 0.140 Uiso 1 1 calc R U . . .
C15 C 0.2517(3) 0.58266(18) 0.6128(8) 0.0819(15) Uani 1 1 d . . . . .
H15 H 0.3022 0.5925 0.6069 0.098 Uiso 1 1 calc R U . . .
C16 C 0.2040(3) 0.59147(16) 0.4632(8) 0.0766(14) Uani 1 1 d . . . . .
C17 C 0.3219(2) 0.67721(14) 0.2740(6) 0.0599(11) Uani 1 1 d . . . . .
C18 C 0.2996(3) 0.70633(16) 0.4175(7) 0.0713(13) Uani 1 1 d . . . . .
H18 H 0.2742 0.6923 0.5196 0.086 Uiso 1 1 calc R U . . .
C19 C 0.3133(3) 0.75572(18) 0.4171(8) 0.0816(14) Uani 1 1 d . . . . .
H19 H 0.2965 0.7752 0.5175 0.098 Uiso 1 1 calc R U . . .
C20 C 0.3496(3) 0.77609(17) 0.2773(9) 0.0819(14) Uani 1 1 d . . . . .
H20 H 0.3598 0.8099 0.2810 0.098 Uiso 1 1 calc R U . . .
C21 C 0.3739(2) 0.74817(18) 0.1209(8) 0.0732(13) Uani 1 1 d . . . . .
C22 C 0.4095(3) 0.7689(2) -0.0304(10) 0.0942(18) Uani 1 1 d . . . . .
H22 H 0.4197 0.8027 -0.0312 0.113 Uiso 1 1 calc R U . . .
C23 C 0.4296(3) 0.7414(3) -0.1755(9) 0.1010(19) Uani 1 1 d . . . . .
H23 H 0.4546 0.7561 -0.2768 0.121 Uiso 1 1 calc R U . . .
C24 C 0.4146(3) 0.6916(2) -0.1808(7) 0.0927(18) Uani 1 1 d . . . . .
H24 H 0.4294 0.6729 -0.2851 0.111 Uiso 1 1 calc R U . . .
C25 C 0.3788(3) 0.66971(18) -0.0370(7) 0.0744(13) Uani 1 1 d . . . . .
H25 H 0.3676 0.6360 -0.0422 0.089 Uiso 1 1 calc R U . . .
C26 C 0.3584(2) 0.69756(17) 0.1212(6) 0.0621(11) 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
N1 C1 1.415(5) . ?
N1 C17 1.423(5) . ?
N1 C7 1.424(6) . ?
C1 C6 1.377(5) . ?
C1 C2 1.386(5) . ?
C2 C3 1.372(6) . ?
C3 C4 1.394(5) . ?
C4 C5 1.390(5) . ?
C4 C4 1.473(6) 2_665 ?
C5 C6 1.378(5) . ?
C7 C8 1.366(7) . ?
C7 C16 1.417(7) . ?
C8 C9 1.354(9) . ?
C9 C10 1.388(11) . ?
C10 C11 1.403(11) . ?
C11 C16 1.417(7) . ?
C11 C12 1.421(12) . ?
C12 C13 1.368(13) . ?
C13 C14 1.346(12) . ?
C14 C15 1.357(9) . ?
C15 C16 1.401(8) . ?
C17 C18 1.370(6) . ?
C17 C26 1.401(6) . ?
C18 C19 1.383(7) . ?
C19 C20 1.327(8) . ?
C20 C21 1.434(8) . ?
C21 C22 1.389(8) . ?
C21 C26 1.422(7) . ?
C22 C23 1.341(10) . ?
C23 C24 1.399(9) . ?
C24 C25 1.362(8) . ?
C25 C26 1.424(7) . ?

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 C17 121.5(3) . . ?
C1 N1 C7 121.5(3) . . ?
C17 N1 C7 116.9(3) . . ?
C6 C1 C2 118.4(3) . . ?
C6 C1 N1 121.4(3) . . ?
C2 C1 N1 120.2(4) . . ?
C3 C2 C1 120.6(4) . . ?
C2 C3 C4 121.8(3) . . ?
C5 C4 C3 116.9(3) . . ?
C5 C4 C4 122.0(4) . 2_665 ?
C3 C4 C4 121.1(4) . 2_665 ?
C6 C5 C4 121.5(4) . . ?
C1 C6 C5 120.9(4) . . ?
C8 C7 C16 119.5(5) . . ?
C8 C7 N1 121.5(5) . . ?
C16 C7 N1 119.0(4) . . ?
C9 C8 C7 122.9(6) . . ?
C8 C9 C10 119.9(7) . . ?
C9 C10 C11 119.3(6) . . ?
C10 C11 C16 120.5(7) . . ?
C10 C11 C12 122.8(8) . . ?
C16 C11 C12 116.7(8) . . ?
C13 C12 C11 121.6(8) . . ?
C14 C13 C12 119.4(8) . . ?
C13 C14 C15 122.7(8) . . ?
C14 C15 C16 119.6(6) . . ?
C15 C16 C7 122.5(5) . . ?
C15 C16 C11 119.7(6) . . ?
C7 C16 C11 117.7(5) . . ?
C18 C17 C26 119.9(4) . . ?
C18 C17 N1 119.1(4) . . ?
C26 C17 N1 120.9(4) . . ?
C17 C18 C19 121.5(5) . . ?
C20 C19 C18 120.3(5) . . ?
C19 C20 C21 121.5(5) . . ?
C22 C21 C26 119.6(6) . . ?
C22 C21 C20 122.7(5) . . ?
C26 C21 C20 117.7(5) . . ?
C23 C22 C21 120.5(6) . . ?
C22 C23 C24 121.5(6) . . ?
C25 C24 C23 120.3(5) . . ?
C24 C25 C26 119.7(5) . . ?
C17 C26 C21 119.1(4) . . ?
C17 C26 C25 122.5(4) . . ?
C21 C26 C25 118.4(4) . . ?

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
C17 N1 C1 C6 20.9(7) . . . . ?
C7 N1 C1 C6 -154.1(4) . . . . ?
C17 N1 C1 C2 -160.1(4) . . . . ?
C7 N1 C1 C2 24.9(7) . . . . ?
C6 C1 C2 C3 -0.7(6) . . . . ?
N1 C1 C2 C3 -179.8(4) . . . . ?
C1 C2 C3 C4 0.4(6) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C2 C3 C4 C4 -180.0(3) . . . 2_665 ?
C3 C4 C5 C6 0.3(6) . . . . ?
C4 C4 C5 C6 -179.9(3) 2_665 . . . ?
C2 C1 C6 C5 0.9(6) . . . . ?
N1 C1 C6 C5 180.0(4) . . . . ?
C4 C5 C6 C1 -0.7(6) . . . . ?
C1 N1 C7 C8 -120.3(5) . . . . ?
C17 N1 C7 C8 64.5(6) . . . . ?
C1 N1 C7 C16 62.3(6) . . . . ?
C17 N1 C7 C16 -112.9(4) . . . . ?
C16 C7 C8 C9 -1.8(7) . . . . ?
N1 C7 C8 C9 -179.2(5) . . . . ?
C7 C8 C9 C10 -1.3(9) . . . . ?
C8 C9 C10 C11 2.1(10) . . . . ?
C9 C10 C11 C16 0.2(9) . . . . ?
C9 C10 C11 C12 -178.9(6) . . . . ?
C10 C11 C12 C13 -176.1(7) . . . . ?
C16 C11 C12 C13 4.7(9) . . . . ?
C11 C12 C13 C14 -0.7(11) . . . . ?
C12 C13 C14 C15 -2.6(11) . . . . ?
C13 C14 C15 C16 1.7(9) . . . . ?
C14 C15 C16 C7 -179.0(4) . . . . ?
C14 C15 C16 C11 2.6(7) . . . . ?
C8 C7 C16 C15 -174.4(4) . . . . ?
N1 C7 C16 C15 3.0(6) . . . . ?
C8 C7 C16 C11 4.1(6) . . . . ?
N1 C7 C16 C11 -178.5(4) . . . . ?
C10 C11 C16 C15 175.3(5) . . . . ?
C12 C11 C16 C15 -5.6(7) . . . . ?
C10 C11 C16 C7 -3.3(7) . . . . ?
C12 C11 C16 C7 175.9(5) . . . . ?
C1 N1 C17 C18 -119.0(5) . . . . ?
C7 N1 C17 C18 56.2(6) . . . . ?
C1 N1 C17 C26 63.8(6) . . . . ?
C7 N1 C17 C26 -121.0(4) . . . . ?
C26 C17 C18 C19 -0.9(7) . . . . ?
N1 C17 C18 C19 -178.1(4) . . . . ?
C17 C18 C19 C20 -1.0(8) . . . . ?
C18 C19 C20 C21 1.8(8) . . . . ?
C19 C20 C21 C22 177.5(5) . . . . ?
C19 C20 C21 C26 -0.7(7) . . . . ?
C26 C21 C22 C23 -0.3(8) . . . . ?
C20 C21 C22 C23 -178.4(5) . . . . ?
C21 C22 C23 C24 1.0(9) . . . . ?
C22 C23 C24 C25 0.0(9) . . . . ?
C23 C24 C25 C26 -1.6(8) . . . . ?
C18 C17 C26 C21 1.9(6) . . . . ?
N1 C17 C26 C21 179.1(4) . . . . ?
C18 C17 C26 C25 -176.1(4) . . . . ?
N1 C17 C26 C25 1.1(6) . . . . ?
C22 C21 C26 C17 -179.4(4) . . . . ?
C20 C21 C26 C17 -1.2(6) . . . . ?
C22 C21 C26 C25 -1.3(6) . . . . ?
C20 C21 C26 C25 176.9(4) . . . . ?
C24 C25 C26 C17 -179.7(4) . . . . ?
C24 C25 C26 C21 2.2(6) . . . . ?

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.035

