# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2012515'
loop_
_audit_author_name
_audit_author_address
'Shi qiang'
;Dalian university of technology
China
;
_audit_update_record             
;
2020-06-27 deposited with the CCDC.	2021-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C43 H32 N2 O'
_chemical_formula_weight         592.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_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                   10.1304(12)
_cell_length_b                   16.9245(19)
_cell_length_c                   19.350(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.357(5)
_cell_angle_gamma                90.00
_cell_volume                     3314.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1972
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      21.58

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9825
_exptl_absorpt_correction_T_max  0.9867
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15864
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5832
_reflns_number_gt                3213
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0740P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    'riding mode'
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5832
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1464
_refine_ls_wR_factor_gt          0.1255
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_restrained_S_all      0.960
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.41296(18) 0.43998(12) 0.09056(10) 0.0526(5) Uani 1 1 d . . .
N1 N 0.10726(15) 0.60466(10) 0.28782(9) 0.0564(5) Uani 1 1 d . . .
O1 O 0.04781(13) 0.54951(9) 0.18161(8) 0.0707(5) Uani 1 1 d . . .
N2 N 0.21961(17) 0.60621(10) 0.33235(9) 0.0602(5) Uani 1 1 d . . .
C5 C 0.12653(18) 0.56122(12) 0.22951(11) 0.0530(5) Uani 1 1 d . . .
C6 C 0.34002(17) 0.55396(13) 0.17239(11) 0.0538(5) Uani 1 1 d . . .
C7 C 0.54988(17) 0.40810(12) 0.10185(10) 0.0498(5) Uani 1 1 d . . .
C8 C 0.31616(19) 0.40556(12) 0.03864(10) 0.0547(5) Uani 1 1 d . . .
C9 C 0.37813(18) 0.49923(13) 0.12959(11) 0.0584(6) Uani 1 1 d . . .
C10 C 0.26694(17) 0.52883(12) 0.23688(10) 0.0512(5) Uani 1 1 d . . .
C11 C 0.31182(19) 0.56622(12) 0.30446(11) 0.0541(5) Uani 1 1 d . . .
C12 C 0.35119(18) 0.63939(13) 0.15460(11) 0.0558(5) Uani 1 1 d . . .
C13 C 0.6559(2) 0.45910(13) 0.10934(11) 0.0649(6) Uani 1 1 d . . .
H13A H 0.6418 0.5132 0.1053 0.078 Uiso 1 1 calc R . .
C14 C 0.3554(2) 0.35516(14) -0.01251(11) 0.0680(6) Uani 1 1 d . . .
H14A H 0.4441 0.3415 -0.0148 0.082 Uiso 1 1 calc R . .
C15 C 0.1828(2) 0.42570(14) 0.03965(12) 0.0663(6) Uani 1 1 d . . .
H15A H 0.1544 0.4601 0.0734 0.080 Uiso 1 1 calc R . .
C16 C -0.0075(2) 0.64768(12) 0.30592(12) 0.0615(6) Uani 1 1 d . . .
C17 C 0.2579(2) 0.43773(13) 0.24436(12) 0.0645(6) Uani 1 1 d . . .
H17A H 0.2249 0.4157 0.2007 0.077 Uiso 1 1 calc R . .
H17B H 0.3462 0.4170 0.2535 0.077 Uiso 1 1 calc R . .
C18 C 0.4423(2) 0.55628(13) 0.33982(13) 0.0670(6) Uani 1 1 d . . .
C19 C 0.5750(2) 0.32799(13) 0.10854(11) 0.0641(6) Uani 1 1 d . . .
H19A H 0.5057 0.2921 0.1034 0.077 Uiso 1 1 calc R . .
C20 C 0.17082(19) 0.41014(12) 0.30067(12) 0.0590(6) Uani 1 1 d . . .
C21 C -0.0172(3) 0.67498(15) 0.37288(14) 0.0850(8) Uani 1 1 d . . .
H21A H 0.0487 0.6638 0.4064 0.102 Uiso 1 1 calc R . .
C22 C 0.7014(2) 0.30074(15) 0.12280(13) 0.0771(7) Uani 1 1 d . . .
H22A H 0.7163 0.2468 0.1280 0.093 Uiso 1 1 calc R . .
C23 C 0.4029(2) 0.69516(15) 0.19996(13) 0.0762(7) Uani 1 1 d . . .
H23A H 0.4300 0.6799 0.2445 0.091 Uiso 1 1 calc R . .
C24 C 0.0415(2) 0.39076(16) 0.28615(14) 0.0892(8) Uani 1 1 d . . .
H24A H 0.0081 0.3953 0.2408 0.107 Uiso 1 1 calc R . .
C25 C 0.2634(3) 0.32453(16) -0.06078(12) 0.0840(8) Uani 1 1 d . . .
H25A H 0.2907 0.2900 -0.0947 0.101 Uiso 1 1 calc R . .
C26 C -0.1065(2) 0.66344(16) 0.25775(14) 0.0907(8) Uani 1 1 d . . .
H26A H -0.1010 0.6445 0.2128 0.109 Uiso 1 1 calc R . .
C27 C 0.3101(2) 0.66502(17) 0.08925(13) 0.0783(7) Uani 1 1 d . . .
H27A H 0.2733 0.6291 0.0576 0.094 Uiso 1 1 calc R . .
C28 C 0.4152(3) 0.77313(17) 0.18080(17) 0.0933(8) Uani 1 1 d . . .
H28A H 0.4507 0.8095 0.2124 0.112 Uiso 1 1 calc R . .
C29 C 0.0930(2) 0.39562(16) -0.00837(14) 0.0806(7) Uani 1 1 d . . .
H29A H 0.0044 0.4097 -0.0068 0.097 Uiso 1 1 calc R . .
C30 C 0.8053(2) 0.35230(17) 0.12940(14) 0.0822(8) Uani 1 1 d . . .
H30A H 0.8906 0.3335 0.1383 0.099 Uiso 1 1 calc R . .
C31 C 0.1326(3) 0.34513(17) -0.05851(14) 0.0873(8) Uani 1 1 d . . .
H31A H 0.0713 0.3248 -0.0909 0.105 Uiso 1 1 calc R . .
C32 C 0.7826(2) 0.43128(16) 0.12276(14) 0.0828(8) Uani 1 1 d . . .
H32A H 0.8527 0.4666 0.1273 0.099 Uiso 1 1 calc R . .
C33 C 0.3763(3) 0.79750(18) 0.11638(18) 0.0914(8) Uani 1 1 d . . .
H33A H 0.3856 0.8501 0.1036 0.110 Uiso 1 1 calc R . .
C34 C 0.2171(3) 0.40125(16) 0.36760(15) 0.0956(9) Uani 1 1 d . . .
H34A H 0.3054 0.4120 0.3789 0.115 Uiso 1 1 calc R . .
C35 C 0.5487(2) 0.52589(14) 0.30620(15) 0.0821(7) Uani 1 1 d . . .
H35A H 0.5381 0.5115 0.2599 0.098 Uiso 1 1 calc R . .
C36 C 0.6878(4) 0.5372(2) 0.4077(2) 0.1265(14) Uani 1 1 d . . .
H36A H 0.7696 0.5309 0.4306 0.152 Uiso 1 1 calc R . .
C37 C -0.2147(3) 0.7073(2) 0.2755(2) 0.1161(11) Uani 1 1 d . . .
H37A H -0.2817 0.7178 0.2425 0.139 Uiso 1 1 calc R . .
C38 C 0.1351(4) 0.3766(2) 0.41864(17) 0.1280(13) Uani 1 1 d . . .
H38A H 0.1679 0.3725 0.4641 0.154 Uiso 1 1 calc R . .
C39 C 0.0072(4) 0.3585(2) 0.4029(2) 0.1169(11) Uani 1 1 d . . .
H39A H -0.0477 0.3418 0.4374 0.140 Uiso 1 1 calc R . .
C40 C 0.3230(3) 0.7434(2) 0.07031(15) 0.0965(9) Uani 1 1 d . . .
H40A H 0.2955 0.7595 0.0261 0.116 Uiso 1 1 calc R . .
C41 C -0.1269(3) 0.71933(18) 0.38936(19) 0.1068(10) Uani 1 1 d . . .
H41A H -0.1343 0.7384 0.4341 0.128 Uiso 1 1 calc R . .
C42 C 0.4606(3) 0.57769(18) 0.40907(14) 0.0979(9) Uani 1 1 d . . .
H42A H 0.3909 0.5986 0.4330 0.117 Uiso 1 1 calc R . .
C43 C -0.0409(3) 0.3648(2) 0.3362(2) 0.1104(11) Uani 1 1 d . . .
H43A H -0.1283 0.3517 0.3247 0.132 Uiso 1 1 calc R . .
C44 C -0.2238(4) 0.73500(19) 0.3403(3) 0.1192(12) Uani 1 1 d . . .
H44A H -0.2966 0.7650 0.3516 0.143 Uiso 1 1 calc R . .
C45 C 0.6711(3) 0.51636(18) 0.3401(2) 0.1084(10) Uani 1 1 d . . .
H45A H 0.7415 0.4957 0.3166 0.130 Uiso 1 1 calc R . .
C46 C 0.5831(4) 0.5676(2) 0.44183(19) 0.1331(14) Uani 1 1 d . . .
H46A H 0.5950 0.5817 0.4881 0.160 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
C1 C9 1.312(3) . ?
C1 C8 1.493(3) . ?
C1 C7 1.496(3) . ?
N1 C5 1.367(2) . ?
N1 N2 1.399(2) . ?
N1 C16 1.427(2) . ?
O1 C5 1.214(2) . ?
N2 C11 1.290(2) . ?
C5 C10 1.526(3) . ?
C6 C9 1.311(3) . ?
C6 C12 1.492(3) . ?
C6 C10 1.537(3) . ?
C7 C13 1.381(3) . ?
C7 C19 1.384(3) . ?
C8 C14 1.378(3) . ?
C8 C15 1.394(3) . ?
C10 C11 1.506(3) . ?
C10 C17 1.552(3) . ?
C11 C18 1.473(3) . ?
C12 C23 1.377(3) . ?
C12 C27 1.385(3) . ?
C13 C32 1.382(3) . ?
C14 C25 1.392(3) . ?
C15 C29 1.372(3) . ?
C16 C26 1.368(3) . ?
C16 C21 1.383(3) . ?
C17 C20 1.504(3) . ?
C18 C35 1.381(3) . ?
C18 C42 1.393(3) . ?
C19 C22 1.378(3) . ?
C20 C34 1.367(3) . ?
C20 C24 1.369(3) . ?
C21 C41 1.389(4) . ?
C22 C30 1.369(3) . ?
C23 C28 1.378(3) . ?
C24 C43 1.376(4) . ?
C25 C31 1.373(3) . ?
C26 C37 1.378(3) . ?
C27 C40 1.384(4) . ?
C28 C33 1.356(4) . ?
C29 C31 1.365(3) . ?
C30 C32 1.361(3) . ?
C33 C40 1.373(4) . ?
C34 C38 1.381(4) . ?
C35 C45 1.388(3) . ?
C36 C45 1.357(5) . ?
C36 C46 1.372(5) . ?
C37 C44 1.344(5) . ?
C38 C39 1.355(4) . ?
C39 C43 1.365(4) . ?
C41 C44 1.364(4) . ?
C42 C46 1.381(4) . ?

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
C9 C1 C8 120.05(18) . . ?
C9 C1 C7 117.46(18) . . ?
C8 C1 C7 122.47(18) . . ?
C5 N1 N2 112.21(15) . . ?
C5 N1 C16 128.47(18) . . ?
N2 N1 C16 119.29(17) . . ?
C11 N2 N1 108.49(16) . . ?
O1 C5 N1 127.31(18) . . ?
O1 C5 C10 126.40(18) . . ?
N1 C5 C10 106.28(16) . . ?
C9 C6 C12 120.79(19) . . ?
C9 C6 C10 118.79(19) . . ?
C12 C6 C10 119.94(17) . . ?
C13 C7 C19 117.60(18) . . ?
C13 C7 C1 120.16(19) . . ?
C19 C7 C1 122.17(18) . . ?
C14 C8 C15 118.0(2) . . ?
C14 C8 C1 121.60(19) . . ?
C15 C8 C1 120.34(19) . . ?
C6 C9 C1 175.1(2) . . ?
C11 C10 C5 100.21(16) . . ?
C11 C10 C6 116.77(16) . . ?
C5 C10 C6 107.64(16) . . ?
C11 C10 C17 110.69(17) . . ?
C5 C10 C17 107.91(15) . . ?
C6 C10 C17 112.51(17) . . ?
N2 C11 C18 121.1(2) . . ?
N2 C11 C10 112.70(16) . . ?
C18 C11 C10 126.05(19) . . ?
C23 C12 C27 117.3(2) . . ?
C23 C12 C6 123.2(2) . . ?
C27 C12 C6 119.4(2) . . ?
C7 C13 C32 121.3(2) . . ?
C8 C14 C25 120.5(2) . . ?
C29 C15 C8 121.1(2) . . ?
C26 C16 C21 119.7(2) . . ?
C26 C16 N1 121.0(2) . . ?
C21 C16 N1 119.4(2) . . ?
C20 C17 C10 114.49(17) . . ?
C35 C18 C42 118.3(2) . . ?
C35 C18 C11 121.8(2) . . ?
C42 C18 C11 119.9(2) . . ?
C22 C19 C7 120.8(2) . . ?
C34 C20 C24 117.1(2) . . ?
C34 C20 C17 122.1(2) . . ?
C24 C20 C17 120.7(2) . . ?
C16 C21 C41 119.0(3) . . ?
C30 C22 C19 120.6(2) . . ?
C12 C23 C28 121.4(2) . . ?
C20 C24 C43 122.4(3) . . ?
C31 C25 C14 120.3(2) . . ?
C16 C26 C37 120.2(3) . . ?
C40 C27 C12 120.9(3) . . ?
C33 C28 C23 120.8(3) . . ?
C31 C29 C15 120.5(2) . . ?
C32 C30 C22 119.4(2) . . ?
C29 C31 C25 119.6(2) . . ?
C30 C32 C13 120.3(2) . . ?
C28 C33 C40 119.1(3) . . ?
C20 C34 C38 121.2(3) . . ?
C18 C35 C45 121.3(3) . . ?
C45 C36 C46 119.5(3) . . ?
C44 C37 C26 120.4(3) . . ?
C39 C38 C34 120.3(3) . . ?
C38 C39 C43 119.8(3) . . ?
C33 C40 C27 120.4(3) . . ?
C44 C41 C21 120.3(3) . . ?
C46 C42 C18 119.4(3) . . ?
C39 C43 C24 119.1(3) . . ?
C37 C44 C41 120.4(3) . . ?
C36 C45 C35 119.9(3) . . ?
C36 C46 C42 121.5(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.037
