# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_4
_database_code_depnum_ccdc_archive 'CCDC 2093120'
loop_
_audit_author_name
_audit_author_address
'Jian Huang'
;Jiangxi Normal University
China
;
_audit_update_record             
;
2021-06-29 deposited with the CCDC.	2021-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H20 N2 O'
_chemical_formula_weight         412.47

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4883(6)
_cell_length_b                   10.7030(9)
_cell_length_c                   10.9775(10)
_cell_angle_alpha                86.863(7)
_cell_angle_beta                 70.062(7)
_cell_angle_gamma                80.112(6)
_cell_volume                     1032.41(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5485
_cell_measurement_theta_min      3.9560
_cell_measurement_theta_max      28.6750

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   'MULTI SCAN'
_exptl_absorpt_correction_T_min  0.81806
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11276
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.37
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3590
_reflns_number_gt                3007
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0575P)²+0.2368P] 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         3590
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1191
_refine_ls_wR_factor_gt          0.1126
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.036
_refine_ls_shift/su_mean         0.003

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
N1 N 0.50197(13) 0.83914(11) 0.37769(11) 0.0328(3) Uani 1 1 d . . .
N2 N 0.73206(14) 0.68852(11) 0.32645(11) 0.0374(3) Uani 1 1 d . . .
O1 O 0.43156(15) 0.93674(12) 0.20962(11) 0.0621(4) Uani 1 1 d . . .
C24 C 0.68368(16) 0.60241(13) 0.57391(13) 0.0336(3) Uani 1 1 d . . .
C4 C 0.60578(16) 0.74362(13) 0.40980(13) 0.0323(3) Uani 1 1 d . . .
C11 C 0.33692(16) 0.85560(13) 0.60450(14) 0.0350(3) Uani 1 1 d . . .
C12 C 0.37069(16) 0.90098(13) 0.47716(14) 0.0345(3) Uani 1 1 d . . .
C9 C 0.56988(16) 0.70214(13) 0.54349(13) 0.0327(3) Uani 1 1 d . . .
C3 C 0.76876(17) 0.72271(14) 0.19834(14) 0.0369(3) Uani 1 1 d . . .
C18 C 0.40333(16) 0.70755(14) 0.77294(14) 0.0363(3) Uani 1 1 d . . .
C10 C 0.44026(16) 0.75307(13) 0.63668(13) 0.0340(3) Uani 1 1 d . . .
C2 C 0.67020(18) 0.80950(14) 0.15400(14) 0.0377(4) Uani 1 1 d . . .
C25 C 0.76746(18) 0.63290(15) 0.64607(14) 0.0405(4) Uani 1 1 d . . .
H25 H 0.7524 0.7156 0.6756 0.049 Uiso 1 1 calc R . .
C1 C 0.52650(18) 0.86779(14) 0.24459(14) 0.0388(4) Uani 1 1 d . . .
C27 C 0.89513(19) 0.41884(15) 0.63425(15) 0.0459(4) Uani 1 1 d . . .
H27 H 0.9668 0.3577 0.6535 0.055 Uiso 1 1 calc R . .
C16 C 0.20356(18) 0.91248(14) 0.70023(15) 0.0416(4) Uani 1 1 d . . .
H16 H 0.1796 0.8799 0.7838 0.050 Uiso 1 1 calc R . .
C23 C 0.36960(18) 0.58658(15) 0.80555(15) 0.0433(4) Uani 1 1 d . . .
H23 H 0.3681 0.5334 0.7419 0.052 Uiso 1 1 calc R . .
C26 C 0.87338(19) 0.54152(16) 0.67455(15) 0.0459(4) Uani 1 1 d . . .
H26 H 0.9305 0.5636 0.7216 0.055 Uiso 1 1 calc R . .
C29 C 0.70588(18) 0.47791(14) 0.53446(15) 0.0429(4) Uani 1 1 d . . .
H29 H 0.6498 0.4554 0.4867 0.051 Uiso 1 1 calc R . .
C15 C 0.10689(18) 1.01418(15) 0.67579(16) 0.0449(4) Uani 1 1 d . . .
C5 C 0.7093(2) 0.83915(16) 0.02193(15) 0.0475(4) Uani 1 1 d . . .
H5 H 0.6431 0.8969 -0.0076 0.057 Uiso 1 1 calc R . .
C28 C 0.8100(2) 0.38672(15) 0.56506(16) 0.0488(4) Uani 1 1 d . . .
H28 H 0.8227 0.3032 0.5388 0.059 Uiso 1 1 calc R . .
C7 C 0.9436(2) 0.69728(17) -0.01942(16) 0.0515(4) Uani 1 1 d . . .
H7 H 1.0360 0.6602 -0.0782 0.062 Uiso 1 1 calc R . .
C19 C 0.4039(2) 0.78492(17) 0.86968(15) 0.0493(4) Uani 1 1 d . . .
H19 H 0.4260 0.8665 0.8497 0.059 Uiso 1 1 calc R . .
C8 C 0.90723(19) 0.66643(16) 0.10882(15) 0.0472(4) Uani 1 1 d . . .
H8 H 0.9743 0.6081 0.1368 0.057 Uiso 1 1 calc R . .
C13 C 0.2756(2) 1.00712(15) 0.45345(16) 0.0499(4) Uani 1 1 d . . .
H13 H 0.2988 1.0416 0.3707 0.060 Uiso 1 1 calc R . .
C14 C 0.1484(2) 1.06111(16) 0.55075(17) 0.0544(5) Uani 1 1 d . . .
H14 H 0.0876 1.1320 0.5320 0.065 Uiso 1 1 calc R . .
C22 C 0.3383(2) 0.54434(18) 0.93147(17) 0.0544(5) Uani 1 1 d . . .
H22 H 0.3159 0.4630 0.9523 0.065 Uiso 1 1 calc R . .
C6 C 0.8443(2) 0.78313(16) -0.06295(15) 0.0506(4) Uani 1 1 d . . .
H6 H 0.8702 0.8026 -0.1507 0.061 Uiso 1 1 calc R . .
C20 C 0.3720(2) 0.7421(2) 0.99573(16) 0.0582(5) Uani 1 1 d . . .
H20 H 0.3723 0.7949 1.0601 0.070 Uiso 1 1 calc R . .
C21 C 0.3401(2) 0.6219(2) 1.02596(16) 0.0584(5) Uani 1 1 d . . .
H21 H 0.3197 0.5929 1.1107 0.070 Uiso 1 1 calc R . .
C17 C -0.0355(2) 1.07287(17) 0.77931(19) 0.0599(5) Uani 1 1 d . . .
H17A H -0.1223 1.0515 0.7640 0.090 Uiso 1 1 calc R . .
H17B H -0.0415 1.1634 0.7777 0.090 Uiso 1 1 calc R . .
H17C H -0.0339 1.0413 0.8625 0.090 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
N1 C4 1.4111(18) . ?
N1 C1 1.4236(18) . ?
N1 C12 1.4319(19) . ?
N2 C4 1.2997(19) . ?
N2 C3 1.3735(18) . ?
O1 C1 1.2165(18) . ?
C24 C25 1.383(2) . ?
C24 C29 1.383(2) . ?
C24 C9 1.493(2) . ?
C4 C9 1.4513(19) . ?
C11 C12 1.402(2) . ?
C11 C16 1.405(2) . ?
C11 C10 1.454(2) . ?
C12 C13 1.396(2) . ?
C9 C10 1.352(2) . ?
C3 C2 1.392(2) . ?
C3 C8 1.403(2) . ?
C18 C19 1.384(2) . ?
C18 C23 1.386(2) . ?
C18 C10 1.4896(19) . ?
C2 C5 1.401(2) . ?
C2 C1 1.445(2) . ?
C25 C26 1.381(2) . ?
C25 H25 0.9300 . ?
C27 C26 1.368(2) . ?
C27 C28 1.374(2) . ?
C27 H27 0.9300 . ?
C16 C15 1.375(2) . ?
C16 H16 0.9300 . ?
C23 C22 1.379(2) . ?
C23 H23 0.9300 . ?
C26 H26 0.9300 . ?
C29 C28 1.379(2) . ?
C29 H29 0.9300 . ?
C15 C14 1.384(2) . ?
C15 C17 1.500(2) . ?
C5 C6 1.361(2) . ?
C5 H5 0.9300 . ?
C28 H28 0.9300 . ?
C7 C8 1.366(2) . ?
C7 C6 1.386(2) . ?
C7 H7 0.9300 . ?
C19 C20 1.382(2) . ?
C19 H19 0.9300 . ?
C8 H8 0.9300 . ?
C13 C14 1.371(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C22 C21 1.370(3) . ?
C22 H22 0.9300 . ?
C6 H6 0.9300 . ?
C20 C21 1.370(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C4 N1 C1 118.66(12) . . ?
C4 N1 C12 120.30(12) . . ?
C1 N1 C12 120.96(12) . . ?
C4 N2 C3 119.24(12) . . ?
C25 C24 C29 118.29(14) . . ?
C25 C24 C9 119.97(13) . . ?
C29 C24 C9 121.71(13) . . ?
N2 C4 N1 124.05(13) . . ?
N2 C4 C9 117.30(12) . . ?
N1 C4 C9 118.64(12) . . ?
C12 C11 C16 118.87(13) . . ?
C12 C11 C10 120.23(13) . . ?
C16 C11 C10 120.88(13) . . ?
C13 C12 C11 118.09(14) . . ?
C13 C12 N1 122.67(13) . . ?
C11 C12 N1 119.22(13) . . ?
C10 C9 C4 121.47(13) . . ?
C10 C9 C24 121.50(12) . . ?
C4 C9 C24 117.01(12) . . ?
N2 C3 C2 121.72(14) . . ?
N2 C3 C8 119.40(13) . . ?
C2 C3 C8 118.86(13) . . ?
C19 C18 C23 118.49(14) . . ?
C19 C18 C10 120.56(14) . . ?
C23 C18 C10 120.95(13) . . ?
C9 C10 C11 119.76(13) . . ?
C9 C10 C18 120.86(13) . . ?
C11 C10 C18 119.37(13) . . ?
C3 C2 C5 120.19(15) . . ?
C3 C2 C1 119.68(13) . . ?
C5 C2 C1 120.12(14) . . ?
C24 C25 C26 120.50(15) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
O1 C1 N1 121.80(14) . . ?
O1 C1 C2 122.24(14) . . ?
N1 C1 C2 115.97(13) . . ?
C26 C27 C28 119.37(15) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C15 C16 C11 122.90(14) . . ?
C15 C16 H16 118.6 . . ?
C11 C16 H16 118.6 . . ?
C22 C23 C18 120.59(16) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
C27 C26 C25 120.67(15) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C28 C29 C24 120.88(15) . . ?
C28 C29 H29 119.6 . . ?
C24 C29 H29 119.6 . . ?
C16 C15 C14 116.61(15) . . ?
C16 C15 C17 122.00(15) . . ?
C14 C15 C17 121.38(15) . . ?
C6 C5 C2 119.79(15) . . ?
C6 C5 H5 120.1 . . ?
C2 C5 H5 120.1 . . ?
C27 C28 C29 120.25(15) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C8 C7 C6 120.77(16) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C20 C19 C18 120.62(16) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C7 C8 C3 120.02(15) . . ?
C7 C8 H8 120.0 . . ?
C3 C8 H8 120.0 . . ?
C14 C13 C12 120.77(15) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 122.57(15) . . ?
C13 C14 H14 118.7 . . ?
C15 C14 H14 118.7 . . ?
C21 C22 C23 120.20(17) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C5 C6 C7 120.37(15) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C21 C20 C19 120.07(17) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 120.03(16) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.051
