# Supplementary Information (SI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_cxy0470_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2913n4
_database_code_depnum_ccdc_archive 'CCDC 2116235'
loop_
_audit_author_name
_audit_author_address
'Xiaoyong Chang'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2023-01-10 deposited with the CCDC.	2024-11-26 downloaded from the CCDC.
;
_audit_creation_date             2018-09-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 N2 O'
_chemical_formula_sum            'C20 H16 N2 O'
_chemical_formula_weight         300.35
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.1908(14)
_cell_length_b                   6.0394(4)
_cell_length_c                   29.880(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.899(3)
_cell_angle_gamma                90
_cell_volume                     2998.0(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6728
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.63
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1002 before and 0.0572 after correction. The Ratio of minimum to maximum transmission is 0.8706. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.29
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            8941
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.626
_diffrn_reflns_theta_min         2.452
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2759
_reflns_number_total             3424
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+3.8528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1213
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.34540(7) 0.2061(2) 0.63450(4) 0.0261(3) Uani 1 1 d . . . . .
H1 H 0.319242 0.134920 0.611355 0.039 Uiso 1 1 calc GR . . . .
N1 N 0.26368(8) -0.4465(2) 0.42431(5) 0.0230(3) Uani 1 1 d . . . . .
N2 N 0.32227(9) 0.9516(2) 0.82734(5) 0.0265(3) Uani 1 1 d . . . . .
C1 C 0.30248(10) 0.7572(3) 0.80593(5) 0.0236(4) Uani 1 1 d . . . . .
H1A H 0.269936 0.659110 0.818170 0.028 Uiso 1 1 calc R . . . .
C2 C 0.32612(9) 0.6892(3) 0.76724(5) 0.0215(4) Uani 1 1 d . . . . .
H2 H 0.310550 0.548002 0.753921 0.026 Uiso 1 1 calc R . . . .
C3 C 0.37324(9) 0.8306(3) 0.74787(5) 0.0195(3) Uani 1 1 d . . . . .
C4 C 0.40477(9) 0.7712(3) 0.70825(5) 0.0211(3) Uani 1 1 d . . . . .
H4 H 0.433365 0.882502 0.696589 0.025 Uiso 1 1 calc R . . . .
C5 C 0.39681(9) 0.5749(3) 0.68719(5) 0.0206(4) Uani 1 1 d . . . . .
H5 H 0.365056 0.466729 0.697355 0.025 Uiso 1 1 calc R . . . .
C6 C 0.43315(9) 0.5119(3) 0.64946(5) 0.0197(3) Uani 1 1 d . . . . .
C7 C 0.40521(9) 0.3204(3) 0.62304(5) 0.0197(3) Uani 1 1 d . . . . .
C8 C 0.43933(9) 0.2575(3) 0.58654(5) 0.0198(3) Uani 1 1 d . . . . .
C9 C 0.40684(9) 0.0658(3) 0.55768(5) 0.0210(3) Uani 1 1 d . . . . .
H9 H 0.388091 -0.055725 0.572195 0.025 Uiso 1 1 calc R . . . .
C10 C 0.40169(9) 0.0497(3) 0.51226(5) 0.0207(3) Uani 1 1 d . . . . .
H10 H 0.427454 0.160258 0.498567 0.025 Uiso 1 1 calc R . . . .
C11 C 0.35885(9) -0.1276(3) 0.48241(5) 0.0194(3) Uani 1 1 d . . . . .
C12 C 0.32621(10) -0.0895(3) 0.43512(5) 0.0214(4) Uani 1 1 d . . . . .
H12 H 0.336161 0.046828 0.421707 0.026 Uiso 1 1 calc R . . . .
C13 C 0.27953(10) -0.2498(3) 0.40791(5) 0.0229(4) Uani 1 1 d . . . . .
H13 H 0.257569 -0.219135 0.375967 0.028 Uiso 1 1 calc R . . . .
C14 C 0.50094(10) 0.3870(3) 0.57755(5) 0.0235(4) Uani 1 1 d . . . . .
H14 H 0.524031 0.346247 0.553068 0.028 Uiso 1 1 calc R . . . .
C15 C 0.52887(10) 0.5729(3) 0.60352(5) 0.0251(4) Uani 1 1 d . . . . .
H15 H 0.571056 0.658486 0.597050 0.030 Uiso 1 1 calc R . . . .
C16 C 0.49514(9) 0.6343(3) 0.63910(5) 0.0226(4) Uani 1 1 d . . . . .
H16 H 0.514646 0.762642 0.656829 0.027 Uiso 1 1 calc R . . . .
C17 C 0.36654(10) 1.0872(3) 0.80851(6) 0.0255(4) Uani 1 1 d . . . . .
H17 H 0.381221 1.226951 0.822793 0.031 Uiso 1 1 calc R . . . .
C18 C 0.39234(10) 1.0365(3) 0.76941(5) 0.0232(4) Uani 1 1 d . . . . .
H18 H 0.422857 1.140993 0.757292 0.028 Uiso 1 1 calc R . . . .
C19 C 0.34402(10) -0.3353(3) 0.49917(5) 0.0214(4) Uani 1 1 d . . . . .
H19 H 0.366237 -0.372497 0.530770 0.026 Uiso 1 1 calc R . . . .
C20 C 0.29695(10) -0.4857(3) 0.46947(6) 0.0235(4) Uani 1 1 d . . . . .
H20 H 0.287427 -0.625508 0.481634 0.028 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 H1 0.8400 . ?
O1 C7 1.3537(19) . ?
N1 C13 1.339(2) . ?
N1 C20 1.344(2) . ?
N2 C1 1.338(2) . ?
N2 C17 1.337(2) . ?
C1 H1A 0.9500 . ?
C1 C2 1.383(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.401(2) . ?
C3 C4 1.468(2) . ?
C3 C18 1.400(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.333(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.473(2) . ?
C6 C7 1.413(2) . ?
C6 C16 1.396(2) . ?
C7 C8 1.417(2) . ?
C8 C9 1.466(2) . ?
C8 C14 1.397(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.341(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.465(2) . ?
C11 C12 1.399(2) . ?
C11 C19 1.399(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.379(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.386(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.377(2) . ?
C20 H20 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 O1 H1 109.5 . . ?
C13 N1 C20 116.72(14) . . ?
C17 N2 C1 116.03(14) . . ?
N2 C1 H1A 117.7 . . ?
N2 C1 C2 124.52(16) . . ?
C2 C1 H1A 117.7 . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.35(16) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 123.86(15) . . ?
C18 C3 C2 116.35(15) . . ?
C18 C3 C4 119.76(15) . . ?
C3 C4 H4 117.1 . . ?
C5 C4 C3 125.72(16) . . ?
C5 C4 H4 117.1 . . ?
C4 C5 H5 117.3 . . ?
C4 C5 C6 125.40(15) . . ?
C6 C5 H5 117.3 . . ?
C7 C6 C5 119.29(14) . . ?
C16 C6 C5 122.09(15) . . ?
C16 C6 C7 118.62(14) . . ?
O1 C7 C6 116.57(13) . . ?
O1 C7 C8 123.34(14) . . ?
C6 C7 C8 120.09(15) . . ?
C7 C8 C9 119.63(15) . . ?
C14 C8 C7 118.82(15) . . ?
C14 C8 C9 121.47(14) . . ?
C8 C9 H9 117.7 . . ?
C10 C9 C8 124.67(15) . . ?
C10 C9 H9 117.7 . . ?
C9 C10 H10 117.9 . . ?
C9 C10 C11 124.14(15) . . ?
C11 C10 H10 117.9 . . ?
C12 C11 C10 120.20(14) . . ?
C19 C11 C10 123.17(14) . . ?
C19 C11 C12 116.53(15) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.04(15) . . ?
C13 C12 H12 120.0 . . ?
N1 C13 C12 123.26(15) . . ?
N1 C13 H13 118.4 . . ?
C12 C13 H13 118.4 . . ?
C8 C14 H14 119.4 . . ?
C15 C14 C8 121.27(15) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.72(16) . . ?
C16 C15 H15 120.1 . . ?
C6 C16 H16 119.3 . . ?
C15 C16 C6 121.48(16) . . ?
C15 C16 H16 119.3 . . ?
N2 C17 H17 118.0 . . ?
N2 C17 C18 124.00(16) . . ?
C18 C17 H17 118.0 . . ?
C3 C18 H18 120.1 . . ?
C17 C18 C3 119.73(16) . . ?
C17 C18 H18 120.1 . . ?
C11 C19 H19 120.3 . . ?
C20 C19 C11 119.46(15) . . ?
C20 C19 H19 120.3 . . ?
N1 C20 C19 123.94(15) . . ?
N1 C20 H20 118.0 . . ?
C19 C20 H20 118.0 . . ?

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 C7 C8 C9 3.1(2) . . . . ?
O1 C7 C8 C14 -179.95(14) . . . . ?
N2 C1 C2 C3 -0.8(2) . . . . ?
N2 C17 C18 C3 -1.2(2) . . . . ?
C1 N2 C17 C18 -0.5(2) . . . . ?
C1 C2 C3 C4 177.02(15) . . . . ?
C1 C2 C3 C18 -0.9(2) . . . . ?
C2 C3 C4 C5 -3.7(2) . . . . ?
C2 C3 C18 C17 1.8(2) . . . . ?
C3 C4 C5 C6 -175.70(14) . . . . ?
C4 C3 C18 C17 -176.18(15) . . . . ?
C4 C5 C6 C7 -165.23(15) . . . . ?
C4 C5 C6 C16 15.4(2) . . . . ?
C5 C6 C7 O1 0.2(2) . . . . ?
C5 C6 C7 C8 179.86(14) . . . . ?
C5 C6 C16 C15 179.92(15) . . . . ?
C6 C7 C8 C9 -176.58(14) . . . . ?
C6 C7 C8 C14 0.4(2) . . . . ?
C7 C6 C16 C15 0.5(2) . . . . ?
C7 C8 C9 C10 144.90(16) . . . . ?
C7 C8 C14 C15 0.2(2) . . . . ?
C8 C9 C10 C11 -170.84(14) . . . . ?
C8 C14 C15 C16 -0.4(2) . . . . ?
C9 C8 C14 C15 177.09(15) . . . . ?
C9 C10 C11 C12 152.29(16) . . . . ?
C9 C10 C11 C19 -23.8(2) . . . . ?
C10 C11 C12 C13 -173.99(15) . . . . ?
C10 C11 C19 C20 174.06(14) . . . . ?
C11 C12 C13 N1 -0.7(2) . . . . ?
C11 C19 C20 N1 0.3(2) . . . . ?
C12 C11 C19 C20 -2.2(2) . . . . ?
C13 N1 C20 C19 1.4(2) . . . . ?
C14 C8 C9 C10 -32.0(2) . . . . ?
C14 C15 C16 C6 0.1(2) . . . . ?
C16 C6 C7 O1 179.58(14) . . . . ?
C16 C6 C7 C8 -0.7(2) . . . . ?
C17 N2 C1 C2 1.5(2) . . . . ?
C18 C3 C4 C5 174.07(15) . . . . ?
C19 C11 C12 C13 2.4(2) . . . . ?
C20 N1 C13 C12 -1.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
