# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_md_zxj372
_database_code_depnum_ccdc_archive 'CCDC 2214177'
loop_
_audit_author_name
_audit_author_address
mtaa
;Yunnan Minzu University
China
;
_audit_update_record             
;
2022-10-20 deposited with the CCDC.	2022-12-08 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C24 H17 N O2'
_chemical_formula_sum            'C24 H17 N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         351.38
_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                   9.6357(6)
_cell_length_b                   12.2218(8)
_cell_length_c                   14.9472(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1760.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9544
_cell_measurement_theta_min      2.9564
_cell_measurement_theta_max      70.0286
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736

_exptl_absorpt_coefficient_mu    0.670
_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  0.57
_exptl_absorpt_correction_T_max  0.91

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            14760
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_theta_min         4.67
_diffrn_reflns_theta_max         70.16
_diffrn_reflns_theta_full        70.16
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             3343
_reflns_number_gt                3180
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0852
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_number_reflns         3343
_refine_ls_number_parameters     245
_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)+(0.0464P)²+0.2115P] 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         0.340
_refine_diff_density_min         -0.225
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1315 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(10)

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       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_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 0.01736(14) 0.50542(12) 0.37504(9) 0.0318(3) Uani d . . . 1 . .
O O2 0.09739(17) 0.31409(13) 0.31453(9) 0.0317(3) Uani d . . . 1 . .
H H4 0.078966 0.380624 0.322118 0.047 Uiso calc U . R 1 . .
N N1 0.31658(18) 0.51420(15) 0.51218(10) 0.0281(4) Uani d . . . 1 . .
H H1 0.397381 0.494235 0.534231 0.034 Uiso calc U . R 1 . .
C C1 0.5163(2) 0.5222(2) 0.20759(15) 0.0413(5) Uani d . . . 1 . .
H H5 0.577396 0.536262 0.159053 0.05 Uiso calc U . R 1 . .
C C2 0.5481(2) 0.4423(2) 0.26969(17) 0.0429(6) Uani d . . . 1 . .
H H8 0.631284 0.401205 0.2638 0.051 Uiso calc U . R 1 . .
C C3 0.4591(2) 0.4221(2) 0.34048(15) 0.0355(5) Uani d . . . 1 . .
H H9 0.4816 0.366802 0.382738 0.043 Uiso calc U . R 1 . .
C C4 0.3368(2) 0.48185(17) 0.35052(13) 0.0272(4) Uani d . . . 1 . .
C C5 0.2489(2) 0.46230(16) 0.43478(12) 0.0264(4) Uani d . . . 1 . .
C C6 0.2272(2) 0.33936(17) 0.45133(13) 0.0260(4) Uani d . . . 1 . .
C C7 0.1604(2) 0.27385(18) 0.38911(12) 0.0269(4) Uani d . . . 1 . .
C C8 0.1588(2) 0.15777(18) 0.39806(13) 0.0276(4) Uani d . . . 1 . .
C C9 0.2182(2) 0.10980(18) 0.47566(13) 0.0289(4) Uani d . . . 1 . .
C C10 0.2149(2) -0.00564(18) 0.48479(14) 0.0337(5) Uani d . . . 1 . .
H H13 0.250146 -0.038607 0.537666 0.04 Uiso calc U . R 1 . .
C C11 0.1613(2) -0.07027(18) 0.41826(15) 0.0352(5) Uani d . . . 1 . .
H H2 0.161339 -0.147621 0.424506 0.042 Uiso calc U . R 1 . .
C C12 0.1687(3) 0.74388(18) 0.63987(15) 0.0368(5) Uani d . . . 1 . .
H H3 0.187158 0.792 0.68834 0.044 Uiso calc U . R 1 . .
C C13 0.2685(2) 0.66872(17) 0.61603(13) 0.0320(4) Uani d . . . 1 . .
H H17 0.355057 0.665225 0.646303 0.038 Uiso calc U . R 1 . .
C C14 0.2372(2) 0.59746(16) 0.54519(12) 0.0266(4) Uani d . . . 1 . .
C C15 0.3958(3) 0.5811(2) 0.21651(14) 0.0398(5) Uani d . . . 1 . .
H H7 0.373757 0.635903 0.173726 0.048 Uiso calc U . R 1 . .
C C16 0.3052(2) 0.56159(19) 0.28758(13) 0.0336(5) Uani d . . . 1 . .
H H6 0.221948 0.602781 0.292888 0.04 Uiso calc U . R 1 . .
C C17 0.1085(2) 0.52450(17) 0.43063(12) 0.0266(4) Uani d . . . 1 . .
C C18 0.1098(2) 0.60508(16) 0.50067(13) 0.0272(4) Uani d . . . 1 . .
C C19 0.0105(2) 0.68309(17) 0.52570(14) 0.0325(5) Uani d . . . 1 . .
H H10 -0.075689 0.688026 0.495139 0.039 Uiso calc U . R 1 . .
C C20 0.0408(3) 0.75229(18) 0.59550(15) 0.0380(5) Uani d . . . 1 . .
H H11 -0.024834 0.80583 0.613702 0.046 Uiso calc U . R 1 . .
C C21 0.2861(2) 0.28842(18) 0.52819(13) 0.0285(4) Uani d . . . 1 . .
H H12 0.330844 0.332557 0.571854 0.034 Uiso calc U . R 1 . .
C C22 0.2801(2) 0.17799(18) 0.54074(13) 0.0307(4) Uani d . . . 1 . .
H H16 0.317798 0.146694 0.593609 0.037 Uiso calc U . R 1 . .
C C23 0.1061(2) -0.02143(19) 0.34043(15) 0.0348(5) Uani d . . . 1 . .
H H14 0.070838 -0.066627 0.293979 0.042 Uiso calc U . R 1 . .
C C24 0.1025(2) 0.08948(19) 0.33075(14) 0.0317(4) Uani d . . . 1 . .
H H15 0.062122 0.120941 0.278772 0.038 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 C17 . 1.231(2) ?
O2 C7 . 1.361(2) ?
O2 H4 . 0.84 ?
N1 C14 . 1.365(3) ?
N1 C5 . 1.472(2) ?
N1 H1 . 0.88 ?
C1 C15 . 1.373(4) ?
C1 C2 . 1.381(4) ?
C1 H5 . 0.95 ?
C2 C3 . 1.384(3) ?
C2 H8 . 0.95 ?
C3 C4 . 1.394(3) ?
C3 H9 . 0.95 ?
C4 C16 . 1.389(3) ?
C4 C5 . 1.536(3) ?
C5 C6 . 1.537(3) ?
C5 C17 . 1.553(3) ?
C6 C7 . 1.386(3) ?
C6 C21 . 1.425(3) ?
C7 C8 . 1.425(3) ?
C8 C24 . 1.415(3) ?
C8 C9 . 1.420(3) ?
C9 C22 . 1.413(3) ?
C9 C10 . 1.418(3) ?
C10 C11 . 1.371(3) ?
C10 H13 . 0.95 ?
C11 C23 . 1.412(3) ?
C11 H2 . 0.95 ?
C12 C13 . 1.377(3) ?
C12 C20 . 1.403(4) ?
C12 H3 . 0.95 ?
C13 C14 . 1.404(3) ?
C13 H17 . 0.95 ?
C14 C18 . 1.399(3) ?
C15 C16 . 1.396(3) ?
C15 H7 . 0.95 ?
C16 H6 . 0.95 ?
C17 C18 . 1.437(3) ?
C18 C19 . 1.401(3) ?
C19 C20 . 1.374(3) ?
C19 H10 . 0.95 ?
C20 H11 . 0.95 ?
C21 C22 . 1.364(3) ?
C21 H12 . 0.95 ?
C22 H16 . 0.95 ?
C23 C24 . 1.364(3) ?
C23 H14 . 0.95 ?
C24 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
C7 O2 H4 . . 109.5 ?
C14 N1 C5 . . 110.93(16) ?
C14 N1 H1 . . 124.5 ?
C5 N1 H1 . . 124.5 ?
C15 C1 C2 . . 119.5(2) ?
C15 C1 H5 . . 120.2 ?
C2 C1 H5 . . 120.2 ?
C1 C2 C3 . . 120.2(2) ?
C1 C2 H8 . . 119.9 ?
C3 C2 H8 . . 119.9 ?
C2 C3 C4 . . 120.8(2) ?
C2 C3 H9 . . 119.6 ?
C4 C3 H9 . . 119.6 ?
C16 C4 C3 . . 118.73(19) ?
C16 C4 C5 . . 122.90(19) ?
C3 C4 C5 . . 118.20(18) ?
N1 C5 C4 . . 109.46(15) ?
N1 C5 C6 . . 110.80(15) ?
C4 C5 C6 . . 111.05(16) ?
N1 C5 C17 . . 101.91(15) ?
C4 C5 C17 . . 111.81(16) ?
C6 C5 C17 . . 111.46(16) ?
C7 C6 C21 . . 118.28(19) ?
C7 C6 C5 . . 121.34(17) ?
C21 C6 C5 . . 120.16(17) ?
O2 C7 C6 . . 123.23(19) ?
O2 C7 C8 . . 115.56(18) ?
C6 C7 C8 . . 121.16(18) ?
C24 C8 C9 . . 119.5(2) ?
C24 C8 C7 . . 121.64(19) ?
C9 C8 C7 . . 118.89(18) ?
C22 C9 C10 . . 122.02(19) ?
C22 C9 C8 . . 119.28(19) ?
C10 C9 C8 . . 118.69(19) ?
C11 C10 C9 . . 120.8(2) ?
C11 C10 H13 . . 119.6 ?
C9 C10 H13 . . 119.6 ?
C10 C11 C23 . . 119.7(2) ?
C10 C11 H2 . . 120.1 ?
C23 C11 H2 . . 120.1 ?
C13 C12 C20 . . 122.7(2) ?
C13 C12 H3 . . 118.7 ?
C20 C12 H3 . . 118.7 ?
C12 C13 C14 . . 117.3(2) ?
C12 C13 H17 . . 121.3 ?
C14 C13 H17 . . 121.3 ?
N1 C14 C18 . . 111.66(17) ?
N1 C14 C13 . . 127.93(19) ?
C18 C14 C13 . . 120.39(19) ?
C1 C15 C16 . . 120.9(2) ?
C1 C15 H7 . . 119.6 ?
C16 C15 H7 . . 119.6 ?
C4 C16 C15 . . 119.9(2) ?
C4 C16 H6 . . 120.1 ?
C15 C16 H6 . . 120.1 ?
O1 C17 C18 . . 128.85(19) ?
O1 C17 C5 . . 123.76(18) ?
C18 C17 C5 . . 107.38(16) ?
C14 C18 C19 . . 121.13(19) ?
C14 C18 C17 . . 107.96(17) ?
C19 C18 C17 . . 130.9(2) ?
C20 C19 C18 . . 118.4(2) ?
C20 C19 H10 . . 120.8 ?
C18 C19 H10 . . 120.8 ?
C19 C20 C12 . . 120.0(2) ?
C19 C20 H11 . . 120.0 ?
C12 C20 H11 . . 120.0 ?
C22 C21 C6 . . 121.76(19) ?
C22 C21 H12 . . 119.1 ?
C6 C21 H12 . . 119.1 ?
C21 C22 C9 . . 120.45(19) ?
C21 C22 H16 . . 119.8 ?
C9 C22 H16 . . 119.8 ?
C24 C23 C11 . . 121.2(2) ?
C24 C23 H14 . . 119.4 ?
C11 C23 H14 . . 119.4 ?
C23 C24 C8 . . 120.1(2) ?
C23 C24 H15 . . 120.0 ?
C8 C24 H15 . . 120.0 ?

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
C15 C1 C2 C3 . . . . -0.1(4) ?
C1 C2 C3 C4 . . . . -0.3(4) ?
C2 C3 C4 C16 . . . . 0.6(3) ?
C2 C3 C4 C5 . . . . -174.8(2) ?
C14 N1 C5 C4 . . . . 114.86(18) ?
C14 N1 C5 C6 . . . . -122.34(17) ?
C14 N1 C5 C17 . . . . -3.6(2) ?
C16 C4 C5 N1 . . . . -100.7(2) ?
C3 C4 C5 N1 . . . . 74.6(2) ?
C16 C4 C5 C6 . . . . 136.67(19) ?
C3 C4 C5 C6 . . . . -48.1(2) ?
C16 C4 C5 C17 . . . . 11.5(3) ?
C3 C4 C5 C17 . . . . -173.29(18) ?
N1 C5 C6 C7 . . . . 177.52(17) ?
C4 C5 C6 C7 . . . . -60.6(2) ?
C17 C5 C6 C7 . . . . 64.8(2) ?
N1 C5 C6 C21 . . . . -7.9(2) ?
C4 C5 C6 C21 . . . . 114.02(19) ?
C17 C5 C6 C21 . . . . -120.60(19) ?
C21 C6 C7 O2 . . . . 178.26(18) ?
C5 C6 C7 O2 . . . . -7.0(3) ?
C21 C6 C7 C8 . . . . -4.3(3) ?
C5 C6 C7 C8 . . . . 170.38(17) ?
O2 C7 C8 C24 . . . . 3.7(3) ?
C6 C7 C8 C24 . . . . -173.92(18) ?
O2 C7 C8 C9 . . . . -177.84(17) ?
C6 C7 C8 C9 . . . . 4.6(3) ?
C24 C8 C9 C22 . . . . 177.06(18) ?
C7 C8 C9 C22 . . . . -1.5(3) ?
C24 C8 C9 C10 . . . . -2.2(3) ?
C7 C8 C9 C10 . . . . 179.24(17) ?
C22 C9 C10 C11 . . . . -176.21(19) ?
C8 C9 C10 C11 . . . . 3.1(3) ?
C9 C10 C11 C23 . . . . -1.3(3) ?
C20 C12 C13 C14 . . . . -1.1(3) ?
C5 N1 C14 C18 . . . . 4.3(2) ?
C5 N1 C14 C13 . . . . -177.36(19) ?
C12 C13 C14 N1 . . . . -177.2(2) ?
C12 C13 C14 C18 . . . . 0.9(3) ?
C2 C1 C15 C16 . . . . 0.2(3) ?
C3 C4 C16 C15 . . . . -0.6(3) ?
C5 C4 C16 C15 . . . . 174.64(19) ?
C1 C15 C16 C4 . . . . 0.2(3) ?
N1 C5 C17 O1 . . . . -179.05(18) ?
C4 C5 C17 O1 . . . . 64.1(2) ?
C6 C5 C17 O1 . . . . -60.8(2) ?
N1 C5 C17 C18 . . . . 1.80(19) ?
C4 C5 C17 C18 . . . . -115.02(17) ?
C6 C5 C17 C18 . . . . 120.02(17) ?
N1 C14 C18 C19 . . . . 178.13(18) ?
C13 C14 C18 C19 . . . . -0.3(3) ?
N1 C14 C18 C17 . . . . -3.0(2) ?
C13 C14 C18 C17 . . . . 178.57(18) ?
O1 C17 C18 C14 . . . . -178.6(2) ?
C5 C17 C18 C14 . . . . 0.5(2) ?
O1 C17 C18 C19 . . . . 0.2(4) ?
C5 C17 C18 C19 . . . . 179.3(2) ?
C14 C18 C19 C20 . . . . -0.2(3) ?
C17 C18 C19 C20 . . . . -178.8(2) ?
C18 C19 C20 C12 . . . . 0.0(3) ?
C13 C12 C20 C19 . . . . 0.6(3) ?
C7 C6 C21 C22 . . . . 1.0(3) ?
C5 C6 C21 C22 . . . . -173.75(18) ?
C6 C21 C22 C9 . . . . 2.0(3) ?
C10 C9 C22 C21 . . . . 177.52(19) ?
C8 C9 C22 C21 . . . . -1.7(3) ?
C10 C11 C23 C24 . . . . -1.3(3) ?
C11 C23 C24 C8 . . . . 2.1(3) ?
C9 C8 C24 C23 . . . . -0.3(3) ?
C7 C8 C24 C23 . . . . 178.2(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H4 O1 . 0.84 1.82 2.623(2) 160.1 ?
C13 H17 O2 4_565 0.95 2.57 3.243(2) 128.2 ?

