# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_CYY0129_20210327
_database_code_depnum_ccdc_archive 'CCDC 2104928'
loop_
_audit_author_name
_audit_author_address
'Yongxiang Liu'
;Shenyang Pharmaceutical University
China
;
_audit_update_record             
;
2021-08-23 deposited with the CCDC.	2022-02-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         316.35
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.4296(3)
_cell_length_b                   7.9065(3)
_cell_length_c                   27.5593(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1618.89(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9050
_cell_measurement_theta_min      5.8219
_cell_measurement_theta_max      58.3146
_cell_measurement_temperature    153.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664

_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.88

_exptl_special_details           
;
;

_diffrn_ambient_temperature      153.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            10097
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_theta_min         5.82
_diffrn_reflns_theta_max         58.31
_diffrn_reflns_theta_full        58.31
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30

_refine_special_details          
;
;

_reflns_number_total             2261
_reflns_number_gt                2238
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0245
_refine_ls_wR_factor_gt          0.0619
_refine_ls_wR_factor_ref         0.0623
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_number_reflns         2261
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0337P)²+0.2292P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.134
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 898 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(4)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.6415(2) 0.24098(17) 0.43448(4) 0.0378(3) Uani d . . . 1 . .
O O2 0.64822(19) 0.01913(16) 0.48559(5) 0.0375(3) Uani d . . . 1 . .
N N1 0.6221(2) 0.29337(19) 0.51270(5) 0.0317(4) Uani d . . . 1 . .
N N2 0.4794(2) 0.8027(2) 0.61356(6) 0.0356(4) Uani d . . . 1 . .
C C1 0.5742(4) 0.2945(3) 0.74464(8) 0.0655(8) Uani d . . . 1 . .
H H1 0.561382 0.268622 0.778123 0.079 Uiso calc U . R 1 . .
C C2 0.4251(4) 0.3029(4) 0.71544(9) 0.0690(8) Uani d . . . 1 . .
H H5 0.309162 0.282385 0.728732 0.083 Uiso calc U . R 1 . .
C C3 0.4430(3) 0.3413(3) 0.66639(8) 0.0516(6) Uani d . . . 1 . .
H H4 0.339071 0.347652 0.646392 0.062 Uiso calc U . R 1 . .
C C4 0.6114(3) 0.3703(2) 0.64658(7) 0.0345(5) Uani d . . . 1 . .
C C5 0.6297(2) 0.4016(2) 0.59334(6) 0.0286(4) Uani d . . . 1 . .
C C6 0.6458(3) 0.5836(2) 0.57475(6) 0.0287(4) Uani d . . . 1 . .
C C7 0.7684(2) 0.6899(2) 0.60641(7) 0.0293(4) Uani d . . . 1 . .
C C8 0.6628(3) 0.8128(2) 0.62858(6) 0.0301(4) Uani d . . . 1 . .
C C9 0.7338(3) 0.9265(3) 0.66139(7) 0.0349(5) Uani d . . . 1 . .
H H12 0.660592 1.010254 0.676264 0.042 Uiso calc U . R 1 . .
C C10 0.9163(3) 0.9140(3) 0.67188(7) 0.0364(5) Uani d . . . 1 . .
H H2 0.968784 0.989858 0.694552 0.044 Uiso calc U . R 1 . .
C C11 0.7416(4) 0.3235(3) 0.72562(8) 0.0552(7) Uani d . . . 1 . .
H H3 0.844711 0.317418 0.745929 0.066 Uiso calc U . R 1 . .
C C12 0.7609(3) 0.3615(3) 0.67696(8) 0.0449(5) Uani d . . . 1 . .
H H16 0.877538 0.381861 0.664078 0.054 Uiso calc U . R 1 . .
C C13 0.7006(3) 0.5893(2) 0.52048(7) 0.0319(4) Uani d . . . 1 . .
H H11 0.67729 0.703771 0.507323 0.038 Uiso calc U . R 1 . .
H H6 0.830988 0.565969 0.517409 0.038 Uiso calc U . R 1 . .
C C14 0.5955(3) 0.4601(2) 0.49152(7) 0.0318(4) Uani d . . . 1 . .
H H10 0.464597 0.48955 0.491842 0.038 Uiso calc U . R 1 . .
C C15 0.6561(3) 0.4235(3) 0.43969(7) 0.0442(5) Uani d . . . 1 . .
H H9 0.577466 0.482009 0.416022 0.053 Uiso calc U . R 1 . .
H H7 0.781769 0.461162 0.434592 0.053 Uiso calc U . R 1 . .
C C16 0.6384(2) 0.1705(2) 0.47900(6) 0.0298(4) Uani d . . . 1 . .
C C17 0.6232(3) 0.2712(2) 0.56294(6) 0.0312(4) Uani d . . . 1 . .
H H8 0.619218 0.159735 0.575776 0.037 Uiso calc U . R 1 . .
C C18 1.0231(3) 0.7921(3) 0.64972(7) 0.0354(5) Uani d . . . 1 . .
H H13 1.147529 0.78587 0.657472 0.042 Uiso calc U . R 1 . .
C C19 0.9504(3) 0.6792(3) 0.61633(7) 0.0323(4) Uani d . . . 1 . .
H H14 1.023845 0.597131 0.600778 0.039 Uiso calc U . R 1 . .
C C20 0.4701(3) 0.6773(3) 0.58424(7) 0.0329(4) Uani d . . . 1 . .
H H15 0.36026 0.644653 0.569294 0.04 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C16 . 1.348(2) ?
O1 C15 . 1.455(2) ?
O2 C16 . 1.213(2) ?
N1 C16 . 1.350(2) ?
N1 C17 . 1.396(2) ?
N1 C14 . 1.455(2) ?
N2 C20 . 1.281(3) ?
N2 C8 . 1.427(3) ?
C1 C11 . 1.369(4) ?
C1 C2 . 1.371(4) ?
C1 H1 . 0.95 ?
C2 C3 . 1.392(3) ?
C2 H5 . 0.95 ?
C3 C4 . 1.384(3) ?
C3 H4 . 0.95 ?
C4 C12 . 1.393(3) ?
C4 C5 . 1.494(3) ?
C5 C17 . 1.329(3) ?
C5 C6 . 1.533(3) ?
C6 C7 . 1.516(3) ?
C6 C20 . 1.523(3) ?
C6 C13 . 1.551(3) ?
C7 C19 . 1.382(3) ?
C7 C8 . 1.390(3) ?
C8 C9 . 1.380(3) ?
C9 C10 . 1.390(3) ?
C9 H12 . 0.95 ?
C10 C18 . 1.390(3) ?
C10 H2 . 0.95 ?
C11 C12 . 1.382(3) ?
C11 H3 . 0.95 ?
C12 H16 . 0.95 ?
C13 C14 . 1.514(3) ?
C13 H11 . 0.99 ?
C13 H6 . 0.99 ?
C14 C15 . 1.525(3) ?
C14 H10 . 1.0 ?
C15 H9 . 0.99 ?
C15 H7 . 0.99 ?
C17 H8 . 0.95 ?
C18 C19 . 1.391(3) ?
C18 H13 . 0.95 ?
C19 H14 . 0.95 ?
C20 H15 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C16 O1 C15 . . 108.77(14) ?
C16 N1 C17 . . 126.28(15) ?
C16 N1 C14 . . 112.85(15) ?
C17 N1 C14 . . 120.84(15) ?
C20 N2 C8 . . 106.11(15) ?
C11 C1 C2 . . 120.1(2) ?
C11 C1 H1 . . 120.0 ?
C2 C1 H1 . . 120.0 ?
C1 C2 C3 . . 120.2(3) ?
C1 C2 H5 . . 119.9 ?
C3 C2 H5 . . 119.9 ?
C4 C3 C2 . . 120.4(2) ?
C4 C3 H4 . . 119.8 ?
C2 C3 H4 . . 119.8 ?
C3 C4 C12 . . 118.40(19) ?
C3 C4 C5 . . 119.82(18) ?
C12 C4 C5 . . 121.71(19) ?
C17 C5 C4 . . 119.17(17) ?
C17 C5 C6 . . 121.36(16) ?
C4 C5 C6 . . 119.39(15) ?
C7 C6 C20 . . 98.45(15) ?
C7 C6 C5 . . 112.02(15) ?
C20 C6 C5 . . 109.42(15) ?
C7 C6 C13 . . 112.42(15) ?
C20 C6 C13 . . 112.10(15) ?
C5 C6 C13 . . 111.72(14) ?
C19 C7 C8 . . 120.52(18) ?
C19 C7 C6 . . 131.94(18) ?
C8 C7 C6 . . 107.52(16) ?
C9 C8 C7 . . 121.86(18) ?
C9 C8 N2 . . 126.26(17) ?
C7 C8 N2 . . 111.88(16) ?
C8 C9 C10 . . 117.55(19) ?
C8 C9 H12 . . 121.2 ?
C10 C9 H12 . . 121.2 ?
C18 C10 C9 . . 121.00(19) ?
C18 C10 H2 . . 119.5 ?
C9 C10 H2 . . 119.5 ?
C1 C11 C12 . . 120.2(2) ?
C1 C11 H3 . . 119.9 ?
C12 C11 H3 . . 119.9 ?
C11 C12 C4 . . 120.7(2) ?
C11 C12 H16 . . 119.6 ?
C4 C12 H16 . . 119.6 ?
C14 C13 C6 . . 110.71(15) ?
C14 C13 H11 . . 109.5 ?
C6 C13 H11 . . 109.5 ?
C14 C13 H6 . . 109.5 ?
C6 C13 H6 . . 109.5 ?
H11 C13 H6 . . 108.1 ?
N1 C14 C13 . . 109.27(15) ?
N1 C14 C15 . . 99.44(15) ?
C13 C14 C15 . . 117.99(17) ?
N1 C14 H10 . . 109.8 ?
C13 C14 H10 . . 109.8 ?
C15 C14 H10 . . 109.8 ?
O1 C15 C14 . . 104.97(16) ?
O1 C15 H9 . . 110.8 ?
C14 C15 H9 . . 110.8 ?
O1 C15 H7 . . 110.8 ?
C14 C15 H7 . . 110.8 ?
H9 C15 H7 . . 108.8 ?
O2 C16 O1 . . 122.92(17) ?
O2 C16 N1 . . 127.79(16) ?
O1 C16 N1 . . 109.29(15) ?
C5 C17 N1 . . 121.88(17) ?
C5 C17 H8 . . 119.1 ?
N1 C17 H8 . . 119.1 ?
C10 C18 C19 . . 120.92(18) ?
C10 C18 H13 . . 119.5 ?
C19 C18 H13 . . 119.5 ?
C7 C19 C18 . . 118.13(18) ?
C7 C19 H14 . . 120.9 ?
C18 C19 H14 . . 120.9 ?
N2 C20 C6 . . 116.01(17) ?
N2 C20 H15 . . 122.0 ?
C6 C20 H15 . . 122.0 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 C1 C2 C3 . . . . -0.2(4) ?
C1 C2 C3 C4 . . . . 0.4(4) ?
C2 C3 C4 C12 . . . . -0.6(3) ?
C2 C3 C4 C5 . . . . 176.5(2) ?
C3 C4 C5 C17 . . . . -78.2(3) ?
C12 C4 C5 C17 . . . . 98.8(2) ?
C3 C4 C5 C6 . . . . 98.7(2) ?
C12 C4 C5 C6 . . . . -84.4(2) ?
C17 C5 C6 C7 . . . . -141.48(19) ?
C4 C5 C6 C7 . . . . 41.7(2) ?
C17 C5 C6 C20 . . . . 110.41(19) ?
C4 C5 C6 C20 . . . . -66.4(2) ?
C17 C5 C6 C13 . . . . -14.3(2) ?
C4 C5 C6 C13 . . . . 168.89(16) ?
C20 C6 C7 C19 . . . . 179.4(2) ?
C5 C6 C7 C19 . . . . 64.4(3) ?
C13 C6 C7 C19 . . . . -62.4(3) ?
C20 C6 C7 C8 . . . . 1.50(18) ?
C5 C6 C7 C8 . . . . -113.51(17) ?
C13 C6 C7 C8 . . . . 119.71(17) ?
C19 C7 C8 C9 . . . . -0.8(3) ?
C6 C7 C8 C9 . . . . 177.46(17) ?
C19 C7 C8 N2 . . . . 179.97(17) ?
C6 C7 C8 N2 . . . . -1.8(2) ?
C20 N2 C8 C9 . . . . -177.95(19) ?
C20 N2 C8 C7 . . . . 1.3(2) ?
C7 C8 C9 C10 . . . . -0.2(3) ?
N2 C8 C9 C10 . . . . 178.95(18) ?
C8 C9 C10 C18 . . . . 0.6(3) ?
C2 C1 C11 C12 . . . . 0.1(4) ?
C1 C11 C12 C4 . . . . -0.3(4) ?
C3 C4 C12 C11 . . . . 0.5(3) ?
C5 C4 C12 C11 . . . . -176.5(2) ?
C7 C6 C13 C14 . . . . 170.57(15) ?
C20 C6 C13 C14 . . . . -79.60(19) ?
C5 C6 C13 C14 . . . . 43.6(2) ?
C16 N1 C14 C13 . . . . -140.84(16) ?
C17 N1 C14 C13 . . . . 41.1(2) ?
C16 N1 C14 C15 . . . . -16.6(2) ?
C17 N1 C14 C15 . . . . 165.33(18) ?
C6 C13 C14 N1 . . . . -56.0(2) ?
C6 C13 C14 C15 . . . . -168.46(16) ?
C16 O1 C15 C14 . . . . -19.5(2) ?
N1 C14 C15 O1 . . . . 20.7(2) ?
C13 C14 C15 O1 . . . . 138.53(18) ?
C15 O1 C16 O2 . . . . -171.1(2) ?
C15 O1 C16 N1 . . . . 9.3(2) ?
C17 N1 C16 O2 . . . . 3.9(3) ?
C14 N1 C16 O2 . . . . -174.07(19) ?
C17 N1 C16 O1 . . . . -176.53(17) ?
C14 N1 C16 O1 . . . . 5.5(2) ?
C4 C5 C17 N1 . . . . 173.71(17) ?
C6 C5 C17 N1 . . . . -3.1(3) ?
C16 N1 C17 C5 . . . . 171.10(18) ?
C14 N1 C17 C5 . . . . -11.1(3) ?
C9 C10 C18 C19 . . . . 0.1(3) ?
C8 C7 C19 C18 . . . . 1.4(3) ?
C6 C7 C19 C18 . . . . -176.36(18) ?
C10 C18 C19 C7 . . . . -1.0(3) ?
C8 N2 C20 C6 . . . . -0.2(2) ?
C7 C6 C20 N2 . . . . -0.8(2) ?
C5 C6 C20 N2 . . . . 116.22(18) ?
C13 C6 C20 N2 . . . . -119.27(18) ?

