# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_c9_auto
_database_code_depnum_ccdc_archive 'CCDC 2364690'
loop_
_audit_author_name
_audit_author_address
CC
;Chongqing University
China
;
_audit_update_record             
;
2024-06-22 deposited with the CCDC.	2025-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24 Cl N O'
_chemical_formula_weight         425.93

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'
Cl Cl 0.3639 0.7018 '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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_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                   10.2452(4)
_cell_length_b                   14.4399(7)
_cell_length_c                   14.5364(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2150.51(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    1.721
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8008
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.32
_diffrn_reflns_theta_max         66.72
_reflns_number_total             3120
_reflns_number_gt                2814
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_number_reflns         3120
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1306
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_restrained_S_all      0.980
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.00060(8) 0.95832(6) 0.16108(6) 0.0636(3) Uani 1 1 d . . .
O1 O 0.7044(2) 0.56395(19) 0.35995(14) 0.0626(7) Uani 1 1 d . . .
N1 N 0.3517(2) 0.71730(16) 0.22296(14) 0.0374(5) Uani 1 1 d . . .
C1 C 0.2250(2) 0.74639(19) 0.23768(15) 0.0338(5) Uani 1 1 d . . .
C2 C 0.1372(3) 0.6969(2) 0.29381(18) 0.0464(7) Uani 1 1 d . . .
H2 H 0.1655 0.6438 0.3240 0.056 Uiso 1 1 calc R . .
C3 C 0.0108(3) 0.7258(3) 0.3045(2) 0.0584(8) Uani 1 1 d . . .
H3 H -0.0457 0.6908 0.3406 0.070 Uiso 1 1 calc R . .
C4 C -0.0351(3) 0.8055(2) 0.2631(2) 0.0544(8) Uani 1 1 d . . .
H4 H -0.1210 0.8248 0.2704 0.065 Uiso 1 1 calc R . .
C5 C 0.0519(3) 0.8551(2) 0.21068(18) 0.0436(6) Uani 1 1 d . . .
C6 C 0.1794(3) 0.8278(2) 0.19704(16) 0.0374(6) Uani 1 1 d . . .
H6 H 0.2349 0.8635 0.1609 0.045 Uiso 1 1 calc R . .
C7 C 0.4279(3) 0.7528(2) 0.14448(18) 0.0408(6) Uani 1 1 d . . .
H7A H 0.4516 0.8172 0.1533 0.049 Uiso 1 1 calc R . .
H7B H 0.3800 0.7466 0.0873 0.049 Uiso 1 1 calc R . .
C8 C 0.5472(3) 0.6908(2) 0.14567(18) 0.0415(6) Uani 1 1 d . . .
H8 H 0.6040 0.7126 0.1954 0.050 Uiso 1 1 calc R . .
C9 C 0.6323(4) 0.6722(3) 0.0639(2) 0.0578(9) Uani 1 1 d . . .
H9 H 0.6275 0.7082 0.0109 0.069 Uiso 1 1 calc R . .
C10 C 0.7146(4) 0.6020(3) 0.0708(2) 0.0633(10) Uani 1 1 d . . .
H10 H 0.7676 0.5880 0.0208 0.076 Uiso 1 1 calc R . .
C11 C 0.7261(3) 0.5436(3) 0.1568(2) 0.0556(8) Uani 1 1 d . . .
H11A H 0.7941 0.5693 0.1956 0.067 Uiso 1 1 calc R . .
H11B H 0.7527 0.4815 0.1395 0.067 Uiso 1 1 calc R . .
C12 C 0.5984(3) 0.5376(2) 0.21299(17) 0.0411(6) Uani 1 1 d . . .
H12 H 0.5686 0.4731 0.2141 0.049 Uiso 1 1 calc R . .
C13 C 0.4904(3) 0.59787(19) 0.17573(15) 0.0387(6) Uani 1 1 d . . .
H13 H 0.4443 0.5673 0.1250 0.046 Uiso 1 1 calc R . .
C14 C 0.3970(2) 0.62551(18) 0.25193(16) 0.0345(6) Uani 1 1 d . . .
H14 H 0.3235 0.5822 0.2545 0.041 Uiso 1 1 calc R . .
C15 C 0.4801(2) 0.61966(18) 0.34441(15) 0.0339(5) Uani 1 1 d . . .
C16 C 0.6100(3) 0.5730(2) 0.31197(17) 0.0403(6) Uani 1 1 d . . .
C17 C 0.5018(3) 0.71491(18) 0.38639(15) 0.0361(6) Uani 1 1 d . . .
C18 C 0.6191(3) 0.7627(2) 0.3813(2) 0.0491(7) Uani 1 1 d . . .
H18 H 0.6901 0.7358 0.3517 0.059 Uiso 1 1 calc R . .
C19 C 0.6316(5) 0.8499(3) 0.4198(2) 0.0638(9) Uani 1 1 d . . .
H19 H 0.7110 0.8810 0.4161 0.077 Uiso 1 1 calc R . .
C20 C 0.5279(5) 0.8910(2) 0.4633(2) 0.0676(11) Uani 1 1 d . . .
H20 H 0.5364 0.9499 0.4884 0.081 Uiso 1 1 calc R . .
C21 C 0.4117(4) 0.8446(2) 0.46966(19) 0.0589(9) Uani 1 1 d . . .
H21 H 0.3413 0.8720 0.4995 0.071 Uiso 1 1 calc R . .
C22 C 0.3985(3) 0.7577(2) 0.43209(17) 0.0449(7) Uani 1 1 d . . .
H22 H 0.3191 0.7269 0.4373 0.054 Uiso 1 1 calc R . .
C23 C 0.4273(2) 0.5503(2) 0.41581(17) 0.0385(6) Uani 1 1 d . . .
C24 C 0.4721(3) 0.5549(2) 0.50585(18) 0.0482(7) Uani 1 1 d . . .
H24 H 0.5275 0.6028 0.5231 0.058 Uiso 1 1 calc R . .
C25 C 0.4356(4) 0.4893(3) 0.5702(2) 0.0570(8) Uani 1 1 d . . .
H25 H 0.4675 0.4932 0.6300 0.068 Uiso 1 1 calc R . .
C26 C 0.3526(4) 0.4185(3) 0.5467(2) 0.0609(9) Uani 1 1 d . . .
H26 H 0.3270 0.3750 0.5903 0.073 Uiso 1 1 calc R . .
C27 C 0.3078(4) 0.4129(3) 0.4579(3) 0.0666(10) Uani 1 1 d . . .
H27 H 0.2515 0.3652 0.4414 0.080 Uiso 1 1 calc R . .
C28 C 0.3454(3) 0.4772(2) 0.3928(2) 0.0517(7) Uani 1 1 d . . .
H28 H 0.3154 0.4715 0.3327 0.062 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
Cl1 C5 1.741(3) . ?
O1 C16 1.199(3) . ?
N1 C1 1.381(3) . ?
N1 C14 1.466(4) . ?
N1 C7 1.474(3) . ?
C1 C6 1.396(4) . ?
C1 C2 1.409(4) . ?
C2 C3 1.369(5) . ?
C3 C4 1.381(5) . ?
C4 C5 1.374(4) . ?
C5 C6 1.379(4) . ?
C7 C8 1.515(4) . ?
C8 C9 1.499(4) . ?
C8 C13 1.526(4) . ?
C9 C10 1.321(5) . ?
C10 C11 1.513(5) . ?
C11 C12 1.545(4) . ?
C12 C13 1.509(4) . ?
C12 C16 1.532(4) . ?
C13 C14 1.517(4) . ?
C14 C15 1.593(3) . ?
C15 C17 1.521(4) . ?
C15 C23 1.540(4) . ?
C15 C16 1.564(4) . ?
C17 C18 1.387(4) . ?
C17 C22 1.395(4) . ?
C18 C19 1.385(5) . ?
C19 C20 1.372(7) . ?
C20 C21 1.369(6) . ?
C21 C22 1.375(5) . ?
C23 C24 1.388(4) . ?
C23 C28 1.389(4) . ?
C24 C25 1.383(4) . ?
C25 C26 1.372(6) . ?
C26 C27 1.372(6) . ?
C27 C28 1.380(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 N1 C14 121.9(2) . . ?
C1 N1 C7 120.8(2) . . ?
C14 N1 C7 111.6(2) . . ?
N1 C1 C6 120.3(2) . . ?
N1 C1 C2 122.4(2) . . ?
C6 C1 C2 117.3(2) . . ?
C3 C2 C1 121.0(3) . . ?
C2 C3 C4 121.7(3) . . ?
C5 C4 C3 117.1(3) . . ?
C4 C5 C6 123.0(3) . . ?
C4 C5 Cl1 118.4(2) . . ?
C6 C5 Cl1 118.5(2) . . ?
C5 C6 C1 119.8(3) . . ?
N1 C7 C8 102.3(2) . . ?
C9 C8 C7 124.5(2) . . ?
C9 C8 C13 107.0(2) . . ?
C7 C8 C13 102.4(2) . . ?
C10 C9 C8 116.6(3) . . ?
C9 C10 C11 122.7(3) . . ?
C10 C11 C12 113.7(3) . . ?
C13 C12 C16 101.6(2) . . ?
C13 C12 C11 113.5(2) . . ?
C16 C12 C11 114.3(2) . . ?
C12 C13 C14 110.62(19) . . ?
C12 C13 C8 109.3(2) . . ?
C14 C13 C8 102.6(2) . . ?
N1 C14 C13 103.16(19) . . ?
N1 C14 C15 117.3(2) . . ?
C13 C14 C15 105.37(19) . . ?
C17 C15 C23 111.65(19) . . ?
C17 C15 C16 112.7(2) . . ?
C23 C15 C16 102.8(2) . . ?
C17 C15 C14 111.6(2) . . ?
C23 C15 C14 114.5(2) . . ?
C16 C15 C14 102.89(18) . . ?
O1 C16 C12 124.9(2) . . ?
O1 C16 C15 123.9(2) . . ?
C12 C16 C15 111.2(2) . . ?
C18 C17 C22 117.6(3) . . ?
C18 C17 C15 123.7(2) . . ?
C22 C17 C15 118.7(2) . . ?
C19 C18 C17 120.8(3) . . ?
C20 C19 C18 120.5(4) . . ?
C21 C20 C19 119.6(3) . . ?
C20 C21 C22 120.3(3) . . ?
C21 C22 C17 121.3(3) . . ?
C24 C23 C28 117.5(3) . . ?
C24 C23 C15 119.2(3) . . ?
C28 C23 C15 123.0(2) . . ?
C25 C24 C23 121.1(3) . . ?
C26 C25 C24 120.6(3) . . ?
C27 C26 C25 119.1(3) . . ?
C26 C27 C28 120.8(4) . . ?
C27 C28 C23 121.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.917
_diffrn_reflns_theta_full        66.72
_diffrn_measured_fraction_theta_full 0.917
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.055
