# Electronic Supplementary Material (ESI) for ChemComm.
# 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_md_zxj4
_database_code_depnum_ccdc_archive 'CCDC 2304224'
loop_
_audit_author_name
_audit_author_address
'Wang M-X'
;Yunnan Minzu University
China
;
_audit_update_record             
;
2023-10-28 deposited with the CCDC.	2024-02-06 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            md_zxj4
_chemical_formula_moiety         'C23 H18 N2 O'
_chemical_formula_sum            'C23 H18 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         338.39
_chemical_absolute_configuration unk

_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                   6.2987(4)
_cell_length_b                   7.8754(5)
_cell_length_c                   36.641(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1817.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9989
_cell_measurement_theta_min      4.8277
_cell_measurement_theta_max      68.1802
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712

_exptl_absorpt_coefficient_mu    0.601
_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  0.80
_exptl_absorpt_correction_T_max  0.98

_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            24679
_diffrn_reflns_av_R_equivalents  0.1563
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         68.52
_diffrn_reflns_theta_full        68.52
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       44

_refine_special_details          
;
;

_reflns_number_total             3343
_reflns_number_gt                2955
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0706
_refine_ls_wR_factor_gt          0.2053
_refine_ls_wR_factor_ref         0.2108
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_number_reflns         3343
_refine_ls_number_parameters     236
_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)+(0.1039P)²+1.9364P] 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         0.458
_refine_diff_density_min         -0.272
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0026(9)
_refine_ls_abs_structure_details 
;

Flack x determined using 1026 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)

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 -0.1758(6) 0.3675(6) 0.31585(11) 0.0400(10) Uani d . . . 1 . .
N N1 0.3883(6) 0.4903(5) 0.38625(12) 0.0245(9) Uani d . . . 1 . .
N N2 0.0518(7) 0.4020(5) 0.38119(12) 0.0272(9) Uani d . . . 1 . .
C C1 0.6750(9) 1.0912(7) 0.38057(15) 0.0347(12) Uani d . . . 1 . .
H H1 0.696595 1.208594 0.375892 0.042 Uiso calc U . R 1 . .
C C2 0.8431(9) 0.9887(7) 0.39158(16) 0.0347(13) Uani d . . . 1 . .
H H5 0.980636 1.036359 0.394527 0.042 Uiso calc U . R 1 . .
C C3 0.8110(9) 0.8183(7) 0.39823(15) 0.0297(11) Uani d . . . 1 . .
H H4 0.92719 0.749316 0.405566 0.036 Uiso calc U . R 1 . .
C C4 0.6084(8) 0.7451(6) 0.39428(13) 0.0248(10) Uani d . . . 1 . .
C C5 0.5888(8) 0.5556(6) 0.40050(15) 0.0273(11) Uani d . . . 1 . .
H H17 0.708319 0.496708 0.388335 0.033 Uiso calc U . R 1 . .
H H6 0.597669 0.531498 0.42698 0.033 Uiso calc U . R 1 . .
C C6 0.3521(8) 0.4579(6) 0.35003(14) 0.0266(10) Uani d . . . 1 . .
H H7 0.451391 0.470126 0.330687 0.032 Uiso calc U . R 1 . .
C C7 0.1445(8) 0.4041(6) 0.34694(14) 0.0273(11) Uani d . . . 1 . .
C C8 0.0203(8) 0.3682(7) 0.31418(14) 0.0293(11) Uani d . . . 1 . .
C C9 0.1298(9) 0.3418(7) 0.27863(15) 0.0329(12) Uani d . . . 1 . .
C C10 0.0286(13) 0.3956(9) 0.24719(17) 0.0503(17) Uani d . . . 1 . .
H H11 -0.10725 0.44751 0.248876 0.06 Uiso calc U . R 1 . .
C C11 0.1223(16) 0.3751(11) 0.21331(19) 0.067(2) Uani d . . . 1 . .
H H8 0.052547 0.41456 0.191934 0.08 Uiso calc U . R 1 . .
C C12 0.3180(17) 0.2969(11) 0.2108(2) 0.068(2) Uani d . . . 1 . .
H H2 0.382757 0.281995 0.18762 0.081 Uiso calc U . R 1 . .
C C13 0.4744(10) 1.0191(7) 0.37652(16) 0.0352(12) Uani d . . . 1 . .
H H3 0.35861 1.087641 0.368828 0.042 Uiso calc U . R 1 . .
C C14 0.4425(8) 0.8489(7) 0.38357(14) 0.0284(11) Uani d . . . 1 . .
H H18 0.304179 0.802258 0.38104 0.034 Uiso calc U . R 1 . .
C C15 0.4198(13) 0.2402(9) 0.2418(2) 0.0551(18) Uani d . . . 1 . .
H H10 0.554101 0.186075 0.239856 0.066 Uiso calc U . R 1 . .
C C16 0.3274(10) 0.2617(7) 0.27604(17) 0.0387(13) Uani d . . . 1 . .
H H9 0.397785 0.222414 0.29737 0.046 Uiso calc U . R 1 . .
C C17 0.2002(8) 0.4542(6) 0.40411(13) 0.0241(10) Uani d . . . 1 . .
C C18 0.1613(8) 0.4724(6) 0.44374(13) 0.0257(10) Uani d . . . 1 . .
C C19 0.2550(9) 0.5983(7) 0.46497(15) 0.0345(13) Uani d . . . 1 . .
H H12 0.349716 0.677275 0.454056 0.041 Uiso calc U . R 1 . .
C C20 0.2109(10) 0.6092(8) 0.50190(16) 0.0377(13) Uani d . . . 1 . .
H H13 0.276794 0.694931 0.516191 0.045 Uiso calc U . R 1 . .
C C21 0.0720(9) 0.4967(7) 0.51816(15) 0.0335(12) Uani d . . . 1 . .
H H14 0.045277 0.502913 0.543642 0.04 Uiso calc U . R 1 . .
C C22 -0.0285(9) 0.3741(8) 0.49698(15) 0.0358(12) Uani d . . . 1 . .
H H15 -0.127551 0.298412 0.507841 0.043 Uiso calc U . R 1 . .
C C23 0.0159(9) 0.3624(7) 0.46016(15) 0.0316(12) Uani d . . . 1 . .
H H16 -0.05335 0.278549 0.445815 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 C8 . 1.237(7) ?
N1 C6 . 1.371(7) ?
N1 C17 . 1.383(7) ?
N1 C5 . 1.460(7) ?
N2 C17 . 1.322(7) ?
N2 C7 . 1.384(7) ?
C1 C2 . 1.391(8) ?
C1 C13 . 1.393(9) ?
C1 H1 . 0.95 ?
C2 C3 . 1.379(8) ?
C2 H5 . 0.95 ?
C3 C4 . 1.408(7) ?
C3 H4 . 0.95 ?
C4 C14 . 1.384(7) ?
C4 C5 . 1.515(7) ?
C5 H17 . 0.99 ?
C5 H6 . 0.99 ?
C6 C7 . 1.379(7) ?
C6 H7 . 0.95 ?
C7 C8 . 1.461(7) ?
C8 C9 . 1.489(7) ?
C9 C10 . 1.383(9) ?
C9 C16 . 1.399(8) ?
C10 C11 . 1.384(10) ?
C10 H11 . 0.95 ?
C11 C12 . 1.381(13) ?
C11 H8 . 0.95 ?
C12 C15 . 1.380(12) ?
C12 H2 . 0.95 ?
C13 C14 . 1.379(8) ?
C13 H3 . 0.95 ?
C14 H18 . 0.95 ?
C15 C16 . 1.392(9) ?
C15 H10 . 0.95 ?
C16 H9 . 0.95 ?
C17 C18 . 1.480(7) ?
C18 C19 . 1.392(8) ?
C18 C23 . 1.397(7) ?
C19 C20 . 1.384(8) ?
C19 H12 . 0.95 ?
C20 C21 . 1.380(8) ?
C20 H13 . 0.95 ?
C21 C22 . 1.391(8) ?
C21 H14 . 0.95 ?
C22 C23 . 1.381(8) ?
C22 H15 . 0.95 ?
C23 H16 . 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
C6 N1 C17 . . 106.1(4) ?
C6 N1 C5 . . 123.8(4) ?
C17 N1 C5 . . 130.1(4) ?
C17 N2 C7 . . 105.9(4) ?
C2 C1 C13 . . 119.0(5) ?
C2 C1 H1 . . 120.5 ?
C13 C1 H1 . . 120.5 ?
C3 C2 C1 . . 120.3(5) ?
C3 C2 H5 . . 119.9 ?
C1 C2 H5 . . 119.9 ?
C2 C3 C4 . . 120.9(5) ?
C2 C3 H4 . . 119.6 ?
C4 C3 H4 . . 119.6 ?
C14 C4 C3 . . 118.1(5) ?
C14 C4 C5 . . 124.3(4) ?
C3 C4 C5 . . 117.5(5) ?
N1 C5 C4 . . 111.3(4) ?
N1 C5 H17 . . 109.4 ?
C4 C5 H17 . . 109.4 ?
N1 C5 H6 . . 109.4 ?
C4 C5 H6 . . 109.4 ?
H17 C5 H6 . . 108.0 ?
N1 C6 C7 . . 107.1(4) ?
N1 C6 H7 . . 126.4 ?
C7 C6 H7 . . 126.4 ?
C6 C7 N2 . . 109.2(4) ?
C6 C7 C8 . . 129.4(5) ?
N2 C7 C8 . . 121.1(5) ?
O1 C8 C7 . . 119.7(5) ?
O1 C8 C9 . . 120.4(5) ?
C7 C8 C9 . . 119.9(5) ?
C10 C9 C16 . . 119.5(6) ?
C10 C9 C8 . . 118.2(6) ?
C16 C9 C8 . . 122.3(5) ?
C9 C10 C11 . . 121.0(7) ?
C9 C10 H11 . . 119.5 ?
C11 C10 H11 . . 119.5 ?
C12 C11 C10 . . 119.5(8) ?
C12 C11 H8 . . 120.3 ?
C10 C11 H8 . . 120.3 ?
C15 C12 C11 . . 120.3(7) ?
C15 C12 H2 . . 119.8 ?
C11 C12 H2 . . 119.8 ?
C14 C13 C1 . . 120.5(5) ?
C14 C13 H3 . . 119.7 ?
C1 C13 H3 . . 119.7 ?
C13 C14 C4 . . 121.2(5) ?
C13 C14 H18 . . 119.4 ?
C4 C14 H18 . . 119.4 ?
C12 C15 C16 . . 120.6(7) ?
C12 C15 H10 . . 119.7 ?
C16 C15 H10 . . 119.7 ?
C15 C16 C9 . . 119.2(7) ?
C15 C16 H9 . . 120.4 ?
C9 C16 H9 . . 120.4 ?
N2 C17 N1 . . 111.7(4) ?
N2 C17 C18 . . 122.5(5) ?
N1 C17 C18 . . 125.9(4) ?
C19 C18 C23 . . 118.6(5) ?
C19 C18 C17 . . 123.2(5) ?
C23 C18 C17 . . 118.1(5) ?
C20 C19 C18 . . 120.4(5) ?
C20 C19 H12 . . 119.8 ?
C18 C19 H12 . . 119.8 ?
C21 C20 C19 . . 120.6(5) ?
C21 C20 H13 . . 119.7 ?
C19 C20 H13 . . 119.7 ?
C20 C21 C22 . . 119.5(5) ?
C20 C21 H14 . . 120.2 ?
C22 C21 H14 . . 120.2 ?
C23 C22 C21 . . 119.9(5) ?
C23 C22 H15 . . 120.0 ?
C21 C22 H15 . . 120.0 ?
C22 C23 C18 . . 120.8(5) ?
C22 C23 H16 . . 119.6 ?
C18 C23 H16 . . 119.6 ?

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
C13 C1 C2 C3 . . . . 0.2(9) ?
C1 C2 C3 C4 . . . . -0.4(9) ?
C2 C3 C4 C14 . . . . 0.0(8) ?
C2 C3 C4 C5 . . . . 177.4(5) ?
C6 N1 C5 C4 . . . . 78.8(6) ?
C17 N1 C5 C4 . . . . -98.8(6) ?
C14 C4 C5 N1 . . . . 12.5(7) ?
C3 C4 C5 N1 . . . . -164.7(4) ?
C17 N1 C6 C7 . . . . 0.2(5) ?
C5 N1 C6 C7 . . . . -177.9(4) ?
N1 C6 C7 N2 . . . . -0.4(5) ?
N1 C6 C7 C8 . . . . 173.8(5) ?
C17 N2 C7 C6 . . . . 0.3(5) ?
C17 N2 C7 C8 . . . . -174.4(5) ?
C6 C7 C8 O1 . . . . -159.8(6) ?
N2 C7 C8 O1 . . . . 13.8(8) ?
C6 C7 C8 C9 . . . . 17.0(8) ?
N2 C7 C8 C9 . . . . -169.4(5) ?
O1 C8 C9 C10 . . . . 30.4(8) ?
C7 C8 C9 C10 . . . . -146.4(6) ?
O1 C8 C9 C16 . . . . -148.2(6) ?
C7 C8 C9 C16 . . . . 35.0(8) ?
C16 C9 C10 C11 . . . . -1.6(11) ?
C8 C9 C10 C11 . . . . 179.8(7) ?
C9 C10 C11 C12 . . . . 1.2(13) ?
C10 C11 C12 C15 . . . . -0.3(14) ?
C2 C1 C13 C14 . . . . 0.5(9) ?
C1 C13 C14 C4 . . . . -1.0(8) ?
C3 C4 C14 C13 . . . . 0.8(8) ?
C5 C4 C14 C13 . . . . -176.5(5) ?
C11 C12 C15 C16 . . . . -0.3(13) ?
C12 C15 C16 C9 . . . . -0.1(11) ?
C10 C9 C16 C15 . . . . 1.0(9) ?
C8 C9 C16 C15 . . . . 179.6(6) ?
C7 N2 C17 N1 . . . . -0.2(5) ?
C7 N2 C17 C18 . . . . 178.9(4) ?
C6 N1 C17 N2 . . . . 0.0(5) ?
C5 N1 C17 N2 . . . . 177.9(4) ?
C6 N1 C17 C18 . . . . -179.1(4) ?
C5 N1 C17 C18 . . . . -1.1(8) ?
N2 C17 C18 C19 . . . . -145.6(5) ?
N1 C17 C18 C19 . . . . 33.4(8) ?
N2 C17 C18 C23 . . . . 31.4(7) ?
N1 C17 C18 C23 . . . . -149.7(5) ?
C23 C18 C19 C20 . . . . 2.6(8) ?
C17 C18 C19 C20 . . . . 179.6(5) ?
C18 C19 C20 C21 . . . . -0.6(9) ?
C19 C20 C21 C22 . . . . -1.7(9) ?
C20 C21 C22 C23 . . . . 1.9(9) ?
C21 C22 C23 C18 . . . . 0.1(9) ?
C19 C18 C23 C22 . . . . -2.4(8) ?
C17 C18 C23 C22 . . . . -179.4(5) ?

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
C5 H17 N2 1_655 0.99 2.30 3.235(7) 156.5 ?
C6 H7 O1 1_655 0.95 2.54 3.304(6) 137.3 ?



