# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_ic18822
_database_code_depnum_ccdc_archive 'CCDC 1988872'
loop_
_audit_author_name
_audit_author_address
Liou
;National Taiwan University
Taiwan
;
_audit_update_record             
;
2020-03-07 deposited with the CCDC.	2020-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H36 N2 O4'
_chemical_formula_weight         608.71

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   17.0973(4)
_cell_length_b                   9.9802(2)
_cell_length_c                   18.6266(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3178.34(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3414
_cell_measurement_theta_min      3.4940
_cell_measurement_theta_max      77.3990

_exptl_crystal_description       column
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1288
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95176
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.2496
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6983
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         5.13
_diffrn_reflns_theta_max         67.98
_reflns_number_total             2880
_reflns_number_gt                2296
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_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)+(0.0820P)²+0.4581P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2880
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1354
_refine_ls_wR_factor_gt          0.1236
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.003
_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
O1 O -0.32142(8) 0.70546(15) 0.72306(7) 0.0516(4) Uani 1 1 d . . .
O2 O 0.02875(7) 0.48538(13) 0.38702(8) 0.0476(4) Uani 1 1 d . . .
N1 N -0.29015(8) 0.56123(17) 0.43572(8) 0.0416(4) Uani 1 1 d . . .
C1 C -0.34918(10) 0.55745(18) 0.38300(9) 0.0342(4) Uani 1 1 d . . .
C2 C -0.42531(10) 0.51971(18) 0.40060(9) 0.0375(4) Uani 1 1 d . . .
H2A H -0.4373 0.4946 0.4486 0.045 Uiso 1 1 calc R . .
C3 C -0.48380(10) 0.51838(17) 0.34912(9) 0.0375(4) Uani 1 1 d . . .
H3A H -0.5353 0.4931 0.3626 0.045 Uiso 1 1 calc R . .
C4 C -0.46868(10) 0.55351(16) 0.27749(9) 0.0338(4) Uani 1 1 d . . .
C5 C -0.39211(10) 0.58973(16) 0.26080(9) 0.0340(4) Uani 1 1 d . . .
H5A H -0.3798 0.6135 0.2127 0.041 Uiso 1 1 calc R . .
C6 C -0.33328(10) 0.59216(17) 0.31210(9) 0.0343(4) Uani 1 1 d . . .
H6A H -0.2818 0.6177 0.2987 0.041 Uiso 1 1 calc R . .
C7 C -0.30623(9) 0.59413(18) 0.50870(9) 0.0347(4) Uani 1 1 d . . .
C8 C -0.35405(10) 0.69955(18) 0.52764(9) 0.0355(4) Uani 1 1 d . . .
H8A H -0.3817 0.7469 0.4914 0.043 Uiso 1 1 calc R . .
C9 C -0.36233(10) 0.73751(17) 0.59916(9) 0.0358(4) Uani 1 1 d . . .
H9A H -0.3963 0.8091 0.6117 0.043 Uiso 1 1 calc R . .
C10 C -0.32102(10) 0.67092(19) 0.65178(9) 0.0369(4) Uani 1 1 d . . .
C11 C -0.27451(11) 0.5623(2) 0.63362(9) 0.0418(4) Uani 1 1 d . . .
H11A H -0.2472 0.5147 0.6700 0.050 Uiso 1 1 calc R . .
C12 C -0.26785(11) 0.52332(19) 0.56309(10) 0.0405(4) Uani 1 1 d . . .
H12A H -0.2369 0.4475 0.5512 0.049 Uiso 1 1 calc R . .
C13 C -0.20954(10) 0.54377(18) 0.41743(8) 0.0350(4) Uani 1 1 d . . .
C14 C -0.15392(10) 0.63272(19) 0.44420(9) 0.0404(4) Uani 1 1 d . . .
H14A H -0.1704 0.7097 0.4701 0.049 Uiso 1 1 calc R . .
C15 C -0.07533(11) 0.61016(19) 0.43349(10) 0.0408(4) Uani 1 1 d . . .
H15A H -0.0379 0.6700 0.4533 0.049 Uiso 1 1 calc R . .
C16 C -0.05063(10) 0.50055(18) 0.39395(9) 0.0353(4) Uani 1 1 d . . .
C17 C -0.10556(10) 0.41460(17) 0.36442(9) 0.0361(4) Uani 1 1 d . . .
H17A H -0.0891 0.3410 0.3358 0.043 Uiso 1 1 calc R . .
C18 C -0.18477(10) 0.43629(18) 0.37676(9) 0.0355(4) Uani 1 1 d . . .
H18A H -0.2222 0.3765 0.3570 0.043 Uiso 1 1 calc R . .
C19 C -0.38202(14) 0.7902(2) 0.74676(11) 0.0590(6) Uani 1 1 d . . .
H19A H -0.3760 0.8072 0.7983 0.089 Uiso 1 1 calc R . .
H19B H -0.4326 0.7471 0.7379 0.089 Uiso 1 1 calc R . .
H19C H -0.3796 0.8752 0.7206 0.089 Uiso 1 1 calc R . .
C20 C 0.05693(12) 0.3641(2) 0.35776(14) 0.0620(6) Uani 1 1 d . . .
H20A H 0.1142 0.3667 0.3557 0.093 Uiso 1 1 calc R . .
H20B H 0.0359 0.3524 0.3092 0.093 Uiso 1 1 calc R . .
H20C H 0.0402 0.2891 0.3881 0.093 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
O1 C10 1.372(2) . ?
O1 C19 1.408(3) . ?
O2 C16 1.372(2) . ?
O2 C20 1.412(3) . ?
N1 C1 1.409(2) . ?
N1 C7 1.425(2) . ?
N1 C13 1.430(2) . ?
C1 C6 1.392(2) . ?
C1 C2 1.394(2) . ?
C2 C3 1.385(2) . ?
C3 C4 1.403(2) . ?
C4 C5 1.393(2) . ?
C4 C4 1.482(3) 3_455 ?
C5 C6 1.388(2) . ?
C7 C8 1.378(2) . ?
C7 C12 1.399(2) . ?
C8 C9 1.392(2) . ?
C9 C10 1.379(2) . ?
C10 C11 1.386(3) . ?
C11 C12 1.375(2) . ?
C13 C18 1.380(3) . ?
C13 C14 1.393(3) . ?
C14 C15 1.377(3) . ?
C15 C16 1.385(3) . ?
C16 C17 1.386(2) . ?
C17 C18 1.391(2) . ?

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
C10 O1 C19 117.26(15) . . ?
C16 O2 C20 117.93(14) . . ?
C1 N1 C7 122.19(14) . . ?
C1 N1 C13 121.40(14) . . ?
C7 N1 C13 116.19(13) . . ?
C6 C1 C2 118.20(15) . . ?
C6 C1 N1 120.98(16) . . ?
C2 C1 N1 120.81(16) . . ?
C3 C2 C1 120.91(16) . . ?
C2 C3 C4 121.51(16) . . ?
C5 C4 C3 116.74(15) . . ?
C5 C4 C4 121.65(19) . 3_455 ?
C3 C4 C4 121.60(19) . 3_455 ?
C6 C5 C4 122.14(16) . . ?
C5 C6 C1 120.49(16) . . ?
C8 C7 C12 118.59(16) . . ?
C8 C7 N1 122.30(16) . . ?
C12 C7 N1 118.94(16) . . ?
C7 C8 C9 120.86(16) . . ?
C10 C9 C8 119.80(16) . . ?
O1 C10 C9 124.36(17) . . ?
O1 C10 C11 115.82(16) . . ?
C9 C10 C11 119.82(16) . . ?
C12 C11 C10 120.13(16) . . ?
C11 C12 C7 120.68(17) . . ?
C18 C13 C14 118.84(16) . . ?
C18 C13 N1 121.42(16) . . ?
C14 C13 N1 119.65(16) . . ?
C15 C14 C13 120.67(17) . . ?
C14 C15 C16 120.25(16) . . ?
O2 C16 C15 116.04(15) . . ?
O2 C16 C17 124.39(16) . . ?
C15 C16 C17 119.56(16) . . ?
C16 C17 C18 119.87(16) . . ?
C13 C18 C17 120.71(16) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        67.98
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.048
