# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2106756'
loop_
_audit_author_name
_audit_author_address
'Qi Di' 'Jilin University'
_audit_update_record             
;
2021-09-01 deposited with the CCDC.	2021-10-08 downloaded from the CCDC.
;
_audit_creation_date             2021-09-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H16 N2 O2'
_chemical_formula_sum            'C20 H16 N2 O2'
_chemical_formula_weight         316.35
_chemical_melting_point          ?
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   32.003(4)
_cell_length_b                   4.9042(6)
_cell_length_c                   20.488(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.159(4)
_cell_angle_gamma                90.00
_cell_volume                     3174.6(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9840
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      31.55
_cell_measurement_theta_min      2.56
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.7037
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            30821
_diffrn_reflns_theta_full        31.58
_diffrn_reflns_theta_max         31.58
_diffrn_reflns_theta_min         2.56
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                4352
_reflns_number_total             5308
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         5308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0564P)²+2.3841P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1233
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C10(H10), C11(H11), C14(H14), C15(H15), C17(H17),
 C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C18(H18a,H18b,H18c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.40689(3) 1.11398(18) 0.26724(4) 0.02523(18) Uani 1 1 d . . .
O2 O 0.33326(2) 0.46109(17) 0.58838(4) 0.02316(17) Uani 1 1 d . . .
N1 N 0.51482(3) -0.5102(2) 0.59119(5) 0.0267(2) Uani 1 1 d . . .
N2 N 0.26086(3) 1.30806(18) 0.36876(4) 0.01918(18) Uani 1 1 d . . .
C1 C 0.43586(4) 0.9150(3) 0.29861(6) 0.0274(2) Uani 1 1 d . . .
H1A H 0.4453 0.9674 0.3442 0.041 Uiso 1 1 calc R . .
H1B H 0.4601 0.9034 0.2756 0.041 Uiso 1 1 calc R . .
H1C H 0.4219 0.7390 0.2973 0.041 Uiso 1 1 calc R . .
C2 C 0.37091(3) 1.1582(2) 0.29431(5) 0.0191(2) Uani 1 1 d . . .
C3 C 0.36111(3) 1.0178(2) 0.34881(5) 0.01751(19) Uani 1 1 d . . .
H3 H 0.3794 0.8838 0.3700 0.021 Uiso 1 1 calc R . .
C4 C 0.32305(3) 1.0815(2) 0.37144(5) 0.01642(18) Uani 1 1 d . . .
C5 C 0.30263(3) 0.9870(2) 0.42549(5) 0.01681(19) Uani 1 1 d . . .
C6 C 0.31474(3) 0.7912(2) 0.47671(5) 0.01684(18) Uani 1 1 d . . .
H6 H 0.2967 0.7795 0.5086 0.020 Uiso 1 1 calc R . .
C7 C 0.34828(3) 0.6206(2) 0.48596(5) 0.01595(18) Uani 1 1 d . . .
H7 H 0.3669 0.6140 0.4548 0.019 Uiso 1 1 calc R . .
C8 C 0.35553(3) 0.4461(2) 0.54463(5) 0.01557(18) Uani 1 1 d . . .
C9 C 0.39114(3) 0.24265(19) 0.55254(5) 0.01457(17) Uani 1 1 d . . .
C10 C 0.39951(3) 0.0988(2) 0.61225(5) 0.01799(19) Uani 1 1 d . . .
H10 H 0.3836 0.1365 0.6460 0.022 Uiso 1 1 calc R . .
C11 C 0.43091(3) -0.0982(2) 0.62212(5) 0.01886(19) Uani 1 1 d . . .
H11 H 0.4365 -0.1929 0.6625 0.023 Uiso 1 1 calc R . .
C12 C 0.45416(3) -0.1548(2) 0.57147(5) 0.01651(18) Uani 1 1 d . . .
C13 C 0.48750(3) -0.3554(2) 0.58206(5) 0.01929(19) Uani 1 1 d . . .
C14 C 0.34370(4) 1.3599(2) 0.26171(5) 0.0220(2) Uani 1 1 d . . .
H14 H 0.3512 1.4515 0.2250 0.026 Uiso 1 1 calc R . .
C15 C 0.30625(4) 1.4232(2) 0.28335(5) 0.0213(2) Uani 1 1 d . . .
H15 H 0.2880 1.5573 0.2620 0.026 Uiso 1 1 calc R . .
C16 C 0.29623(3) 1.2825(2) 0.33786(5) 0.01813(19) Uani 1 1 d . . .
C17 C 0.26501(3) 1.1342(2) 0.42068(5) 0.01871(19) Uani 1 1 d . . .
H17 H 0.2452 1.1152 0.4496 0.022 Uiso 1 1 calc R . .
C18 C 0.22537(4) 1.4905(2) 0.34797(6) 0.0235(2) Uani 1 1 d . . .
H18A H 0.2033 1.4562 0.3744 0.035 Uiso 1 1 calc R . .
H18B H 0.2143 1.4587 0.3017 0.035 Uiso 1 1 calc R . .
H18C H 0.2348 1.6781 0.3539 0.035 Uiso 1 1 calc R . .
C19 C 0.44591(3) -0.0152(2) 0.51140(5) 0.01673(18) Uani 1 1 d . . .
H19 H 0.4613 -0.0562 0.4772 0.020 Uiso 1 1 calc R . .
C20 C 0.41482(3) 0.1848(2) 0.50256(5) 0.01568(18) Uani 1 1 d . . .
H20 H 0.4097 0.2821 0.4626 0.019 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 C1 1.4265(15) . ?
O1 C2 1.3726(13) . ?
O2 C8 1.2330(12) . ?
N1 C13 1.1504(14) . ?
N2 C16 1.3879(14) . ?
N2 C17 1.3533(13) . ?
N2 C18 1.4552(13) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.3895(14) . ?
C2 C14 1.4132(15) . ?
C3 H3 0.9400 . ?
C3 C4 1.4055(14) . ?
C4 C5 1.4486(14) . ?
C4 C16 1.4119(14) . ?
C5 C6 1.4298(14) . ?
C5 C17 1.3939(14) . ?
C6 H6 0.9400 . ?
C6 C7 1.3502(14) . ?
C7 H7 0.9400 . ?
C7 C8 1.4638(13) . ?
C8 C9 1.5039(13) . ?
C9 C10 1.4005(13) . ?
C9 C20 1.3967(13) . ?
C10 H10 0.9400 . ?
C10 C11 1.3856(14) . ?
C11 H11 0.9400 . ?
C11 C12 1.3976(14) . ?
C12 C13 1.4420(14) . ?
C12 C19 1.3965(14) . ?
C14 H14 0.9400 . ?
C14 C15 1.3779(17) . ?
C15 H15 0.9400 . ?
C15 C16 1.3929(15) . ?
C17 H17 0.9400 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 H19 0.9400 . ?
C19 C20 1.3879(14) . ?
C20 H20 0.9400 . ?

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
C2 O1 C1 116.93(9) . . ?
C16 N2 C18 125.26(9) . . ?
C17 N2 C16 108.45(9) . . ?
C17 N2 C18 126.29(10) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 123.89(10) . . ?
O1 C2 C14 114.39(9) . . ?
C3 C2 C14 121.71(10) . . ?
C2 C3 H3 120.9 . . ?
C2 C3 C4 118.24(9) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 C5 134.51(9) . . ?
C3 C4 C16 119.07(9) . . ?
C16 C4 C5 106.42(9) . . ?
C6 C5 C4 132.34(9) . . ?
C17 C5 C4 105.67(9) . . ?
C17 C5 C6 121.99(9) . . ?
C5 C6 H6 115.3 . . ?
C7 C6 C5 129.47(10) . . ?
C7 C6 H6 115.3 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.74(9) . . ?
C8 C7 H7 120.1 . . ?
O2 C8 C7 121.84(9) . . ?
O2 C8 C9 118.50(9) . . ?
C7 C8 C9 119.66(8) . . ?
C10 C9 C8 117.68(9) . . ?
C20 C9 C8 123.10(9) . . ?
C20 C9 C10 119.17(9) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.81(9) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.31(9) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C13 119.50(9) . . ?
C19 C12 C11 120.57(9) . . ?
C19 C12 C13 119.92(9) . . ?
N1 C13 C12 178.22(12) . . ?
C2 C14 H14 119.7 . . ?
C15 C14 C2 120.51(10) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 121.0 . . ?
C14 C15 C16 117.99(10) . . ?
C16 C15 H15 121.0 . . ?
N2 C16 C4 108.52(9) . . ?
N2 C16 C15 129.01(10) . . ?
C15 C16 C4 122.47(10) . . ?
N2 C17 C5 110.95(9) . . ?
N2 C17 H17 124.5 . . ?
C5 C17 H17 124.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C12 C19 H19 120.2 . . ?
C20 C19 C12 119.51(9) . . ?
C20 C19 H19 120.2 . . ?
C9 C20 H20 119.7 . . ?
C19 C20 C9 120.61(9) . . ?
C19 C20 H20 119.7 . . ?

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
O1 C2 C3 C4 -179.61(9) . . . . ?
O1 C2 C14 C15 179.43(9) . . . . ?
O2 C8 C9 C10 -5.86(14) . . . . ?
O2 C8 C9 C20 171.70(10) . . . . ?
C1 O1 C2 C3 -1.33(15) . . . . ?
C1 O1 C2 C14 179.20(10) . . . . ?
C2 C3 C4 C5 -178.79(10) . . . . ?
C2 C3 C4 C16 0.55(14) . . . . ?
C2 C14 C15 C16 -0.11(16) . . . . ?
C3 C2 C14 C15 -0.05(16) . . . . ?
C3 C4 C5 C6 0.71(19) . . . . ?
C3 C4 C5 C17 179.89(11) . . . . ?
C3 C4 C16 N2 179.61(9) . . . . ?
C3 C4 C16 C15 -0.74(15) . . . . ?
C4 C5 C6 C7 -5.68(19) . . . . ?
C4 C5 C17 N2 0.07(11) . . . . ?
C5 C4 C16 N2 -0.88(11) . . . . ?
C5 C4 C16 C15 178.77(9) . . . . ?
C5 C6 C7 C8 176.72(10) . . . . ?
C6 C5 C17 N2 179.36(9) . . . . ?
C6 C7 C8 O2 -4.39(15) . . . . ?
C6 C7 C8 C9 175.83(9) . . . . ?
C7 C8 C9 C10 173.92(9) . . . . ?
C7 C8 C9 C20 -8.52(14) . . . . ?
C8 C9 C10 C11 177.82(9) . . . . ?
C8 C9 C20 C19 -176.66(9) . . . . ?
C9 C10 C11 C12 -0.53(16) . . . . ?
C10 C9 C20 C19 0.86(14) . . . . ?
C10 C11 C12 C13 178.61(10) . . . . ?
C10 C11 C12 C19 -0.12(15) . . . . ?
C11 C12 C13 N1 -87(4) . . . . ?
C11 C12 C19 C20 1.13(15) . . . . ?
C12 C19 C20 C9 -1.50(15) . . . . ?
C13 C12 C19 C20 -177.60(9) . . . . ?
C14 C2 C3 C4 -0.17(15) . . . . ?
C14 C15 C16 N2 -179.92(10) . . . . ?
C14 C15 C16 C4 0.51(15) . . . . ?
C16 N2 C17 C5 -0.63(12) . . . . ?
C16 C4 C5 C6 -178.68(10) . . . . ?
C16 C4 C5 C17 0.49(11) . . . . ?
C17 N2 C16 C4 0.94(11) . . . . ?
C17 N2 C16 C15 -178.67(10) . . . . ?
C17 C5 C6 C7 175.25(10) . . . . ?
C18 N2 C16 C4 -178.63(9) . . . . ?
C18 N2 C16 C15 1.75(17) . . . . ?
C18 N2 C17 C5 178.94(9) . . . . ?
C19 C12 C13 N1 91(4) . . . . ?
C20 C9 C10 C11 0.17(15) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
