# Supplementary Information (SI) 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_xjx033
_database_code_depnum_ccdc_archive 'CCDC 2336953'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2024-03-02 deposited with the CCDC.	2024-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 N2 O3'
_chemical_formula_sum            'C24 H18 N2 O3'
_chemical_formula_weight         382.40

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.6718(3)
_cell_length_b                   9.0165(3)
_cell_length_c                   24.3506(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1903.96(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9931
_cell_measurement_theta_min      3.63
_cell_measurement_theta_max      79.13

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.138
_exptl_absorpt_coefficient_mu    0.720
_shelx_estimated_absorpt_T_min   0.715
_shelx_estimated_absorpt_T_max   0.907
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.5866
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12022
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.630
_diffrn_reflns_theta_max         79.911
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4015
_reflns_number_gt                3719
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_max     0.952
_reflns_Friedel_fraction_full    0.994

_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. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0901P)²+0.1835P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1449 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.05(13)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4015
_refine_ls_number_parameters     266
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1429
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.8523(2) 0.6708(2) 0.59594(8) 0.0375(4) Uani 1 1 d . . . . .
O2 O 0.9889(3) 0.6693(3) 0.76318(9) 0.0468(5) Uani 1 1 d . . . . .
O3 O 0.8224(3) 0.9945(3) 0.63293(11) 0.0563(6) Uani 1 1 d . . . . .
N1 N 0.8920(2) 0.5028(2) 0.66394(9) 0.0340(4) Uani 1 1 d . . . . .
N2 N 0.9201(3) 0.8582(3) 0.70434(10) 0.0398(5) Uani 1 1 d D . . . .
H2N H 0.976(4) 0.927(4) 0.7194(15) 0.044(9) Uiso 1 1 d D . . . .
C1 C 0.9096(3) 0.5368(3) 0.61351(10) 0.0337(5) Uani 1 1 d . . . . .
C2 C 0.8046(3) 0.6234(3) 0.68931(10) 0.0335(5) Uani 1 1 d . . . . .
C3 C 0.9173(3) 0.7148(3) 0.72478(11) 0.0372(5) Uani 1 1 d . . . . .
C4 C 0.8354(3) 0.8794(3) 0.65748(12) 0.0404(6) Uani 1 1 d . . . . .
C5 C 0.7624(3) 0.7294(3) 0.64117(11) 0.0352(5) Uani 1 1 d . . . . .
C11 C 0.9804(3) 0.4437(3) 0.57105(11) 0.0365(5) Uani 1 1 d . . . . .
C12 C 0.9949(3) 0.2917(3) 0.58101(12) 0.0435(6) Uani 1 1 d . . . . .
H12 H 0.961153 0.250929 0.614917 0.052 Uiso 1 1 calc R U . . .
C13 C 1.0586(4) 0.2010(4) 0.54125(15) 0.0545(8) Uani 1 1 d . . . . .
H13 H 1.065919 0.097235 0.547413 0.065 Uiso 1 1 calc R U . . .
C14 C 1.1120(5) 0.2614(5) 0.49220(16) 0.0631(10) Uani 1 1 d . . . . .
H14 H 1.158987 0.199396 0.465456 0.076 Uiso 1 1 calc R U . . .
C15 C 1.0965(5) 0.4129(5) 0.48241(14) 0.0624(10) Uani 1 1 d . . . . .
H15 H 1.132802 0.454224 0.448924 0.075 Uiso 1 1 calc R U . . .
C16 C 1.0286(4) 0.5029(4) 0.52128(12) 0.0475(7) Uani 1 1 d . . . . .
H16 H 1.014760 0.605587 0.514004 0.057 Uiso 1 1 calc R U . . .
C21 C 0.6754(3) 0.5656(3) 0.72744(11) 0.0389(6) Uani 1 1 d . . . . .
H21A H 0.723910 0.514642 0.759024 0.047 Uiso 1 1 calc R U . . .
H21B H 0.618091 0.652029 0.742047 0.047 Uiso 1 1 calc R U . . .
C22 C 0.5615(3) 0.4610(3) 0.70141(10) 0.0366(5) Uani 1 1 d . . . . .
C23 C 0.6092(3) 0.3258(3) 0.67875(12) 0.0416(6) Uani 1 1 d . . . . .
H23 H 0.714212 0.296497 0.681260 0.050 Uiso 1 1 calc R U . . .
C24 C 0.5034(4) 0.2350(3) 0.65269(13) 0.0496(7) Uani 1 1 d . . . . .
H24 H 0.537080 0.144599 0.636618 0.060 Uiso 1 1 calc R U . . .
C25 C 0.3496(4) 0.2737(4) 0.64972(14) 0.0512(7) Uani 1 1 d . . . . .
H25 H 0.278642 0.212134 0.630655 0.061 Uiso 1 1 calc R U . . .
C26 C 0.2995(4) 0.4030(4) 0.67472(14) 0.0496(7) Uani 1 1 d . . . . .
H26 H 0.193112 0.427909 0.674369 0.060 Uiso 1 1 calc R U . . .
C27 C 0.4051(3) 0.4962(3) 0.70035(12) 0.0424(6) Uani 1 1 d . . . . .
H27 H 0.370089 0.584940 0.717330 0.051 Uiso 1 1 calc R U . . .
C31 C 0.5950(3) 0.7426(3) 0.62332(11) 0.0370(5) Uani 1 1 d . . . . .
C32 C 0.5406(3) 0.6577(3) 0.57993(12) 0.0433(6) Uani 1 1 d . . . . .
H32 H 0.608473 0.592942 0.560886 0.052 Uiso 1 1 calc R U . . .
C33 C 0.3861(4) 0.6676(4) 0.56425(15) 0.0524(7) Uani 1 1 d . . . . .
H33 H 0.348797 0.608597 0.534795 0.063 Uiso 1 1 calc R U . . .
C34 C 0.2875(4) 0.7625(4) 0.59125(16) 0.0522(8) Uani 1 1 d . . . . .
H34 H 0.182510 0.769232 0.580355 0.063 Uiso 1 1 calc R U . . .
C35 C 0.3416(4) 0.8480(4) 0.63425(15) 0.0509(7) Uani 1 1 d . . . . .
H35 H 0.273821 0.913880 0.652778 0.061 Uiso 1 1 calc R U . . .
C36 C 0.4955(3) 0.8378(3) 0.65055(13) 0.0438(6) Uani 1 1 d . . . . .
H36 H 0.532092 0.896177 0.680308 0.053 Uiso 1 1 calc R U . . .


_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 1.375(3) . ?
O1 C5 1.449(3) . ?
O2 C3 1.195(4) . ?
O3 C4 1.202(4) . ?
N1 C1 1.275(3) . ?
N1 C2 1.462(3) . ?
N2 C4 1.370(4) . ?
N2 C3 1.386(4) . ?
C1 C11 1.467(4) . ?
C2 C3 1.543(4) . ?
C2 C21 1.545(4) . ?
C2 C5 1.556(4) . ?
C4 C5 1.546(4) . ?
C5 C31 1.520(3) . ?
C11 C16 1.389(4) . ?
C11 C12 1.397(4) . ?
C12 C13 1.383(4) . ?
C13 C14 1.392(6) . ?
C14 C15 1.393(7) . ?
C15 C16 1.379(5) . ?
C21 C22 1.506(4) . ?
C22 C27 1.394(4) . ?
C22 C23 1.401(4) . ?
C23 C24 1.384(5) . ?
C24 C25 1.380(5) . ?
C25 C26 1.385(5) . ?
C26 C27 1.391(5) . ?
C31 C36 1.386(4) . ?
C31 C32 1.387(4) . ?
C32 C33 1.396(4) . ?
C33 C34 1.377(5) . ?
C34 C35 1.382(5) . ?
C35 C36 1.395(5) . ?

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
C1 O1 C5 106.16(19) . . ?
C1 N1 C2 106.9(2) . . ?
C4 N2 C3 114.8(2) . . ?
N1 C1 O1 117.9(2) . . ?
N1 C1 C11 126.2(2) . . ?
O1 C1 C11 115.8(2) . . ?
N1 C2 C3 107.8(2) . . ?
N1 C2 C21 112.3(2) . . ?
C3 C2 C21 107.6(2) . . ?
N1 C2 C5 105.1(2) . . ?
C3 C2 C5 104.0(2) . . ?
C21 C2 C5 119.2(2) . . ?
O2 C3 N2 126.3(3) . . ?
O2 C3 C2 125.7(3) . . ?
N2 C3 C2 108.0(2) . . ?
O3 C4 N2 125.8(3) . . ?
O3 C4 C5 126.1(3) . . ?
N2 C4 C5 108.1(2) . . ?
O1 C5 C31 109.0(2) . . ?
O1 C5 C4 107.1(2) . . ?
C31 C5 C4 113.3(2) . . ?
O1 C5 C2 102.8(2) . . ?
C31 C5 C2 119.2(2) . . ?
C4 C5 C2 104.3(2) . . ?
C16 C11 C12 120.1(3) . . ?
C16 C11 C1 121.4(3) . . ?
C12 C11 C1 118.5(2) . . ?
C13 C12 C11 119.6(3) . . ?
C12 C13 C14 120.2(4) . . ?
C13 C14 C15 119.9(3) . . ?
C16 C15 C14 120.1(3) . . ?
C15 C16 C11 120.1(3) . . ?
C22 C21 C2 115.7(2) . . ?
C27 C22 C23 118.6(3) . . ?
C27 C22 C21 120.2(3) . . ?
C23 C22 C21 121.1(3) . . ?
C24 C23 C22 120.0(3) . . ?
C25 C24 C23 121.0(3) . . ?
C24 C25 C26 119.5(3) . . ?
C25 C26 C27 120.0(3) . . ?
C26 C27 C22 120.7(3) . . ?
C36 C31 C32 119.6(3) . . ?
C36 C31 C5 120.4(2) . . ?
C32 C31 C5 120.0(2) . . ?
C31 C32 C33 120.0(3) . . ?
C34 C33 C32 120.4(3) . . ?
C33 C34 C35 119.8(3) . . ?
C34 C35 C36 120.3(3) . . ?
C31 C36 C35 120.0(3) . . ?

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
C2 N1 C1 O1 2.2(3) . . . . ?
C2 N1 C1 C11 -175.2(2) . . . . ?
C5 O1 C1 N1 -8.7(3) . . . . ?
C5 O1 C1 C11 168.9(2) . . . . ?
C1 N1 C2 C3 -105.7(2) . . . . ?
C1 N1 C2 C21 136.0(2) . . . . ?
C1 N1 C2 C5 4.8(3) . . . . ?
C4 N2 C3 O2 175.6(3) . . . . ?
C4 N2 C3 C2 -4.5(3) . . . . ?
N1 C2 C3 O2 -61.2(4) . . . . ?
C21 C2 C3 O2 60.1(4) . . . . ?
C5 C2 C3 O2 -172.4(3) . . . . ?
N1 C2 C3 N2 119.0(2) . . . . ?
C21 C2 C3 N2 -119.7(2) . . . . ?
C5 C2 C3 N2 7.7(3) . . . . ?
C3 N2 C4 O3 -179.7(3) . . . . ?
C3 N2 C4 C5 -0.8(3) . . . . ?
C1 O1 C5 C31 -117.0(2) . . . . ?
C1 O1 C5 C4 120.0(2) . . . . ?
C1 O1 C5 C2 10.4(2) . . . . ?
O3 C4 C5 O1 76.0(4) . . . . ?
N2 C4 C5 O1 -102.9(2) . . . . ?
O3 C4 C5 C31 -44.2(4) . . . . ?
N2 C4 C5 C31 136.9(2) . . . . ?
O3 C4 C5 C2 -175.4(3) . . . . ?
N2 C4 C5 C2 5.7(3) . . . . ?
N1 C2 C5 O1 -9.4(2) . . . . ?
C3 C2 C5 O1 103.8(2) . . . . ?
C21 C2 C5 O1 -136.4(2) . . . . ?
N1 C2 C5 C31 111.2(3) . . . . ?
C3 C2 C5 C31 -135.6(2) . . . . ?
C21 C2 C5 C31 -15.7(4) . . . . ?
N1 C2 C5 C4 -121.1(2) . . . . ?
C3 C2 C5 C4 -7.9(3) . . . . ?
C21 C2 C5 C4 112.0(3) . . . . ?
N1 C1 C11 C16 -163.8(3) . . . . ?
O1 C1 C11 C16 18.8(3) . . . . ?
N1 C1 C11 C12 18.0(4) . . . . ?
O1 C1 C11 C12 -159.4(2) . . . . ?
C16 C11 C12 C13 0.6(4) . . . . ?
C1 C11 C12 C13 178.8(3) . . . . ?
C11 C12 C13 C14 1.8(5) . . . . ?
C12 C13 C14 C15 -2.2(6) . . . . ?
C13 C14 C15 C16 0.1(6) . . . . ?
C14 C15 C16 C11 2.3(6) . . . . ?
C12 C11 C16 C15 -2.6(5) . . . . ?
C1 C11 C16 C15 179.2(3) . . . . ?
N1 C2 C21 C22 -55.8(3) . . . . ?
C3 C2 C21 C22 -174.3(2) . . . . ?
C5 C2 C21 C22 67.7(3) . . . . ?
C2 C21 C22 C27 -120.9(3) . . . . ?
C2 C21 C22 C23 60.3(3) . . . . ?
C27 C22 C23 C24 4.3(4) . . . . ?
C21 C22 C23 C24 -176.9(3) . . . . ?
C22 C23 C24 C25 -1.6(5) . . . . ?
C23 C24 C25 C26 -2.1(5) . . . . ?
C24 C25 C26 C27 3.0(5) . . . . ?
C25 C26 C27 C22 -0.2(4) . . . . ?
C23 C22 C27 C26 -3.4(4) . . . . ?
C21 C22 C27 C26 177.7(3) . . . . ?
O1 C5 C31 C36 -158.7(2) . . . . ?
C4 C5 C31 C36 -39.5(4) . . . . ?
C2 C5 C31 C36 83.9(3) . . . . ?
O1 C5 C31 C32 22.1(3) . . . . ?
C4 C5 C31 C32 141.2(3) . . . . ?
C2 C5 C31 C32 -95.4(3) . . . . ?
C36 C31 C32 C33 -0.6(5) . . . . ?
C5 C31 C32 C33 178.7(3) . . . . ?
C31 C32 C33 C34 0.7(5) . . . . ?
C32 C33 C34 C35 -0.3(6) . . . . ?
C33 C34 C35 C36 -0.3(5) . . . . ?
C32 C31 C36 C35 0.0(5) . . . . ?
C5 C31 C36 C35 -179.3(3) . . . . ?
C34 C35 C36 C31 0.5(5) . . . . ?

_refine_diff_density_max         0.289
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.055



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Et2O, PE'
