# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_071918b_huang
_database_code_depnum_ccdc_archive 'CCDC 1879174'
_audit_update_record             
;
2018-11-15 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H23 N3 O'
_chemical_formula_weight         513.57

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           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.6951(4)
_cell_length_b                   7.5970(3)
_cell_length_c                   38.1721(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.378(4)
_cell_angle_gamma                90.00
_cell_volume                     2521.47(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    2703
_cell_measurement_theta_min      9.0790
_cell_measurement_theta_max      71.4480

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85369
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Enhance Ultra Cu x-ray source'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1270
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9452
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         4.63
_diffrn_reflns_theta_max         68.23
_reflns_number_total             4607
_reflns_number_gt                3639
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0786P)²+2.6376P] 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_number_reflns         4607
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.1931
_refine_ls_wR_factor_gt          0.1802
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2694(2) 0.7902(3) 1.02296(6) 0.0504(6) Uani 1 1 d . . .
N1 N 0.5086(3) 0.8624(3) 1.04224(6) 0.0363(6) Uani 1 1 d . . .
N2 N 0.7371(3) 0.9362(3) 1.06720(7) 0.0448(6) Uani 1 1 d . . .
N3 N 1.1784(3) 0.3372(4) 0.83118(7) 0.0453(7) Uani 1 1 d . . .
C1 C 0.4725(4) 0.9369(4) 1.07553(7) 0.0378(7) Uani 1 1 d . . .
C2 C 0.6132(4) 0.9770(4) 1.08982(8) 0.0419(7) Uani 1 1 d . . .
C3 C 0.6203(4) 1.0498(4) 1.12284(8) 0.0501(8) Uani 1 1 d . . .
H3 H 0.7165 1.0763 1.1335 0.060 Uiso 1 1 calc R . .
C4 C 0.4842(4) 1.0832(4) 1.14007(8) 0.0507(8) Uani 1 1 d . . .
H4 H 0.4879 1.1337 1.1628 0.061 Uiso 1 1 calc R . .
C5 C 0.3433(5) 1.0454(5) 1.12524(9) 0.0529(9) Uani 1 1 d . . .
H5 H 0.2520 1.0718 1.1377 0.064 Uiso 1 1 calc R . .
C6 C 0.3329(4) 0.9684(4) 1.09182(9) 0.0498(8) Uani 1 1 d . . .
H6 H 0.2371 0.9398 1.0811 0.060 Uiso 1 1 calc R . .
C7 C 0.4086(3) 0.7892(4) 1.01814(7) 0.0374(6) Uani 1 1 d . . .
C8 C 0.6692(4) 0.8687(4) 1.04014(7) 0.0372(6) Uani 1 1 d . . .
C9 C 0.7425(3) 0.8004(4) 1.00859(7) 0.0349(6) Uani 1 1 d . . .
C10 C 0.8988(4) 0.8119(4) 1.00335(8) 0.0428(7) Uani 1 1 d . . .
H10 H 0.9632 0.8639 1.0207 0.051 Uiso 1 1 calc R . .
C11 C 0.9628(3) 0.7465(4) 0.97217(9) 0.0450(7) Uani 1 1 d . . .
H11 H 1.0695 0.7629 0.9681 0.054 Uiso 1 1 calc R . .
C12 C 0.8759(3) 0.6599(4) 0.94757(7) 0.0349(6) Uani 1 1 d . . .
C13 C 0.7132(3) 0.6477(3) 0.95251(7) 0.0314(6) Uani 1 1 d . . .
C14 C 0.6133(3) 0.5697(4) 0.92754(8) 0.0378(6) Uani 1 1 d . . .
H14 H 0.6555 0.5206 0.9068 0.045 Uiso 1 1 calc R . .
C15 C 0.4576(4) 0.5631(4) 0.93237(8) 0.0432(7) Uani 1 1 d . . .
H15 H 0.3936 0.5097 0.9151 0.052 Uiso 1 1 calc R . .
C16 C 0.3931(3) 0.6337(4) 0.96220(8) 0.0418(7) Uani 1 1 d . . .
H16 H 0.2851 0.6265 0.9655 0.050 Uiso 1 1 calc R . .
C17 C 0.4830(3) 0.7142(3) 0.98721(7) 0.0358(6) Uani 1 1 d . . .
C18 C 0.6469(3) 0.7221(3) 0.98315(7) 0.0310(6) Uani 1 1 d . . .
C19 C 0.9511(3) 0.5780(4) 0.91669(7) 0.0367(6) Uani 1 1 d . . .
C20 C 0.9508(4) 0.3965(4) 0.91244(8) 0.0408(7) Uani 1 1 d . . .
H20 H 0.8977 0.3255 0.9289 0.049 Uiso 1 1 calc R . .
C21 C 1.0259(4) 0.3161(4) 0.88479(7) 0.0414(7) Uani 1 1 d . . .
H21 H 1.0257 0.1914 0.8828 0.050 Uiso 1 1 calc R . .
C22 C 1.1016(3) 0.4174(4) 0.85995(7) 0.0388(7) Uani 1 1 d . . .
C23 C 1.1031(4) 0.5986(5) 0.86400(9) 0.0560(10) Uani 1 1 d . . .
H23 H 1.1541 0.6698 0.8472 0.067 Uiso 1 1 calc R . .
C24 C 1.0311(4) 0.6774(4) 0.89230(9) 0.0543(9) Uani 1 1 d . . .
H24 H 1.0366 0.8016 0.8950 0.065 Uiso 1 1 calc R . .
C25 C 1.1160(3) 0.1926(4) 0.81309(7) 0.0360(6) Uani 1 1 d . . .
C26 C 0.9588(4) 0.1617(5) 0.81195(8) 0.0463(8) Uani 1 1 d . . .
H26 H 0.8907 0.2397 0.8236 0.056 Uiso 1 1 calc R . .
C27 C 0.9003(4) 0.0174(6) 0.79394(8) 0.0580(10) Uani 1 1 d . . .
H27 H 0.7925 -0.0031 0.7937 0.070 Uiso 1 1 calc R . .
C28 C 0.9957(5) -0.0962(5) 0.77645(8) 0.0583(10) Uani 1 1 d . . .
H28 H 0.9550 -0.1953 0.7644 0.070 Uiso 1 1 calc R . .
C29 C 1.1512(4) -0.0639(4) 0.77674(8) 0.0509(8) Uani 1 1 d . . .
H29 H 1.2179 -0.1401 0.7642 0.061 Uiso 1 1 calc R . .
C30 C 1.2124(4) 0.0778(4) 0.79496(8) 0.0424(7) Uani 1 1 d . . .
H30 H 1.3204 0.0969 0.7951 0.051 Uiso 1 1 calc R . .
C31 C 1.3234(3) 0.4081(4) 0.82039(8) 0.0396(7) Uani 1 1 d . . .
C32 C 1.3346(4) 0.4933(5) 0.78848(9) 0.0545(9) Uani 1 1 d . . .
H32 H 1.2460 0.5070 0.7740 0.065 Uiso 1 1 calc R . .
C33 C 1.4747(5) 0.5585(6) 0.77767(10) 0.0671(11) Uani 1 1 d . . .
H33 H 1.4822 0.6165 0.7557 0.080 Uiso 1 1 calc R . .
C34 C 1.6034(5) 0.5401(6) 0.79844(11) 0.0644(11) Uani 1 1 d . . .
H34 H 1.6995 0.5847 0.7908 0.077 Uiso 1 1 calc R . .
C35 C 1.5929(4) 0.4576(5) 0.83010(10) 0.0574(9) Uani 1 1 d . . .
H35 H 1.6817 0.4460 0.8446 0.069 Uiso 1 1 calc R . .
C36 C 1.4529(4) 0.3905(4) 0.84125(8) 0.0467(8) Uani 1 1 d . . .
H36 H 1.4462 0.3325 0.8632 0.056 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 C7 1.225(4) . ?
N1 C7 1.379(4) . ?
N1 C8 1.401(4) . ?
N1 C1 1.428(3) . ?
N2 C8 1.292(4) . ?
N2 C2 1.419(4) . ?
N3 C25 1.405(4) . ?
N3 C22 1.426(3) . ?
N3 C31 1.434(4) . ?
C1 C2 1.371(5) . ?
C1 C6 1.388(4) . ?
C2 C3 1.377(4) . ?
C3 C4 1.381(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.406(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C17 1.466(4) . ?
C8 C9 1.461(4) . ?
C9 C10 1.378(4) . ?
C9 C18 1.406(4) . ?
C10 C11 1.408(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.370(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.431(4) . ?
C12 C19 1.488(4) . ?
C13 C14 1.415(4) . ?
C13 C18 1.425(4) . ?
C14 C15 1.368(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.373(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.436(4) . ?
C19 C20 1.389(4) . ?
C19 C24 1.389(4) . ?
C20 C21 1.387(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.390(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(5) . ?
C23 C24 1.388(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.387(4) . ?
C25 C30 1.397(4) . ?
C26 C27 1.389(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.373(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.374(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.386(5) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C36 1.381(5) . ?
C31 C32 1.384(5) . ?
C32 C33 1.380(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.375(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.365(6) . ?
C34 H34 0.9500 . ?
C35 C36 1.389(5) . ?
C35 H35 0.9500 . ?
C36 H36 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
C7 N1 C8 126.9(2) . . ?
C7 N1 C1 127.8(2) . . ?
C8 N1 C1 105.2(2) . . ?
C8 N2 C2 103.2(3) . . ?
C25 N3 C22 122.1(2) . . ?
C25 N3 C31 119.4(2) . . ?
C22 N3 C31 118.6(2) . . ?
C2 C1 C6 124.4(3) . . ?
C2 C1 N1 104.0(2) . . ?
C6 C1 N1 131.7(3) . . ?
C1 C2 C3 119.2(3) . . ?
C1 C2 N2 112.8(3) . . ?
C3 C2 N2 128.0(3) . . ?
C2 C3 C4 118.5(4) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 121.9(3) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 115.2(3) . . ?
C1 C6 H6 122.4 . . ?
C5 C6 H6 122.4 . . ?
O1 C7 N1 121.1(3) . . ?
O1 C7 C17 124.4(3) . . ?
N1 C7 C17 114.5(2) . . ?
N2 C8 N1 114.7(3) . . ?
N2 C8 C9 126.9(3) . . ?
N1 C8 C9 118.4(3) . . ?
C10 C9 C18 120.4(2) . . ?
C10 C9 C8 122.2(3) . . ?
C18 C9 C8 117.4(3) . . ?
C9 C10 C11 119.7(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 122.0(3) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 118.9(2) . . ?
C11 C12 C19 120.0(3) . . ?
C13 C12 C19 121.1(3) . . ?
C14 C13 C18 117.9(3) . . ?
C14 C13 C12 122.8(2) . . ?
C18 C13 C12 119.2(3) . . ?
C15 C14 C13 121.9(3) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 120.9(3) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 120.3(3) . . ?
C16 C17 C7 118.8(3) . . ?
C18 C17 C7 121.0(3) . . ?
C9 C18 C13 119.6(2) . . ?
C9 C18 C17 121.7(2) . . ?
C13 C18 C17 118.7(3) . . ?
C20 C19 C24 117.5(3) . . ?
C20 C19 C12 120.5(3) . . ?
C24 C19 C12 121.9(3) . . ?
C21 C20 C19 121.7(3) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C20 C21 C22 120.2(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C23 C22 C21 118.6(3) . . ?
C23 C22 N3 120.4(3) . . ?
C21 C22 N3 121.0(3) . . ?
C22 C23 C24 120.7(3) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C23 C24 C19 121.2(3) . . ?
C23 C24 H24 119.4 . . ?
C19 C24 H24 119.4 . . ?
C26 C25 C30 118.2(3) . . ?
C26 C25 N3 121.7(3) . . ?
C30 C25 N3 120.0(3) . . ?
C25 C26 C27 120.4(3) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C28 C27 C26 121.1(3) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C27 C28 C29 118.8(3) . . ?
C27 C28 H28 120.6 . . ?
C29 C28 H28 120.6 . . ?
C28 C29 C30 121.1(3) . . ?
C28 C29 H29 119.4 . . ?
C30 C29 H29 119.4 . . ?
C29 C30 C25 120.3(3) . . ?
C29 C30 H30 119.9 . . ?
C25 C30 H30 119.9 . . ?
C36 C31 C32 119.4(3) . . ?
C36 C31 N3 120.9(3) . . ?
C32 C31 N3 119.7(3) . . ?
C33 C32 C31 119.9(4) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C34 C33 C32 120.5(4) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C35 C34 C33 119.9(3) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C34 C35 C36 120.2(4) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C31 C36 C35 120.0(3) . . ?
C31 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        68.23
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.845
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.052
