# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2282683'
loop_
_audit_author_name
_audit_author_address
'Dong Qiu'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-07-19 deposited with the CCDC.	2024-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H15 Cl N2 O3'
_chemical_formula_weight         414.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   9.8715(15)
_cell_length_b                   10.2631(15)
_cell_length_c                   10.4758(15)
_cell_angle_alpha                92.848(2)
_cell_angle_beta                 100.885(2)
_cell_angle_gamma                108.048(2)
_cell_volume                     984.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2261
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      29.35

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   0.6559
_exptl_transmission_factor_max   0.7462
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.224
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_reflns_number            6792
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_av_R_equivalents  0.0140
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.993
_diffrn_reflns_theta_max         31.324
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.796
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.796
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.796
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             5127
_reflns_number_gt                3475
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.1000P)²+0.3500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5127
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1930
_refine_ls_wR_factor_gt          0.1699
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_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
C1 C 0.4599(2) 0.7778(2) 0.3195(2) 0.0411(4) Uani 1 1 d . . . . .
C2 C 0.4450(3) 0.8789(2) 0.2357(3) 0.0580(6) Uani 1 1 d . . . . .
H2 H 0.4815 0.8843 0.1599 0.070 Uiso 1 1 calc R U . . .
C3 C 0.3752(3) 0.9697(3) 0.2687(3) 0.0713(8) Uani 1 1 d . . . . .
H3 H 0.3664 1.0376 0.2153 0.086 Uiso 1 1 calc R U . . .
C4 C 0.3191(3) 0.9606(3) 0.3789(3) 0.0703(8) Uani 1 1 d . . . . .
H4 H 0.2709 1.0214 0.3983 0.084 Uiso 1 1 calc R U . . .
C5 C 0.3323(3) 0.8644(3) 0.4610(3) 0.0708(8) Uani 1 1 d . . . . .
H5 H 0.2940 0.8594 0.5358 0.085 Uiso 1 1 calc R U . . .
C6 C 0.4044(3) 0.7736(3) 0.4305(2) 0.0544(5) Uani 1 1 d . . . . .
C7 C 0.5351(2) 0.68034(19) 0.28642(19) 0.0389(4) Uani 1 1 d . . . . .
C8 C 0.4667(2) 0.55989(19) 0.20593(19) 0.0379(4) Uani 1 1 d . . . . .
C9 C 0.5376(2) 0.46864(19) 0.17262(19) 0.0390(4) Uani 1 1 d . . . . .
C10 C 0.6856(2) 0.4971(2) 0.22106(19) 0.0401(4) Uani 1 1 d . . . . .
C11 C 0.6874(2) 0.7148(2) 0.3426(2) 0.0416(4) Uani 1 1 d . . . . .
C12 C 0.9060(2) 0.6531(3) 0.3555(3) 0.0576(6) Uani 1 1 d . . . . .
H12 H 0.9542 0.7349 0.4106 0.069 Uiso 1 1 calc R U . . .
C13 C 0.9813(3) 0.5702(3) 0.3269(3) 0.0708(7) Uani 1 1 d . . . . .
H13 H 1.0808 0.5952 0.3622 0.085 Uiso 1 1 calc R U . . .
C14 C 0.9108(3) 0.4475(3) 0.2449(3) 0.0677(7) Uani 1 1 d . . . . .
H14 H 0.9630 0.3903 0.2259 0.081 Uiso 1 1 calc R U . . .
C15 C 0.7669(3) 0.4114(2) 0.1928(3) 0.0539(6) Uani 1 1 d . . . . .
H15 H 0.7204 0.3294 0.1378 0.065 Uiso 1 1 calc R U . . .
C16 C 0.4308(2) 0.3483(2) 0.0902(2) 0.0454(5) Uani 1 1 d . . . . .
C17 C 0.3085(2) 0.4974(2) 0.1407(2) 0.0442(5) Uani 1 1 d . . . . .
C18 C 0.1593(3) 0.2783(2) -0.0011(2) 0.0535(5) Uani 1 1 d . . . . .
H18A H 0.1799 0.2113 -0.0563 0.064 Uiso 1 1 calc R U . . .
H18B H 0.1119 0.3303 -0.0579 0.064 Uiso 1 1 calc R U . . .
C19 C 0.0552(2) 0.2022(2) 0.0798(2) 0.0432(4) Uani 1 1 d . . . . .
C20 C 0.1010(3) 0.1756(3) 0.2050(2) 0.0539(5) Uani 1 1 d . . . . .
H20 H 0.1999 0.2063 0.2440 0.065 Uiso 1 1 calc R U . . .
C21 C -0.0003(3) 0.1030(3) 0.2738(3) 0.0635(6) Uani 1 1 d . . . . .
H21 H 0.0312 0.0855 0.3587 0.076 Uiso 1 1 calc R U . . .
C22 C -0.1459(3) 0.0572(3) 0.2172(3) 0.0631(6) Uani 1 1 d . . . . .
H22 H -0.2131 0.0078 0.2632 0.076 Uiso 1 1 calc R U . . .
C23 C -0.1927(3) 0.0842(3) 0.0927(3) 0.0656(7) Uani 1 1 d . . . . .
H23 H -0.2918 0.0539 0.0544 0.079 Uiso 1 1 calc R U . . .
C24 C -0.0927(3) 0.1561(2) 0.0245(2) 0.0581(6) Uani 1 1 d . . . . .
H24 H -0.1250 0.1740 -0.0600 0.070 Uiso 1 1 calc R U . . .
Cl1 Cl 0.42486(13) 0.65290(10) 0.53406(9) 0.1064(4) Uani 1 1 d . . . . .
N1 N 0.75833(18) 0.61804(17) 0.30398(17) 0.0418(4) Uani 1 1 d . . . . .
N2 N 0.29622(19) 0.37202(18) 0.07577(18) 0.0484(4) Uani 1 1 d . . . . .
O1 O 0.76227(17) 0.81602(17) 0.41900(17) 0.0573(4) Uani 1 1 d . . . . .
O2 O 0.4460(2) 0.24585(16) 0.04107(18) 0.0625(5) Uani 1 1 d . . . . .
O3 O 0.20952(17) 0.54178(18) 0.14216(18) 0.0605(4) Uani 1 1 d . . . . .


_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
C1 C6 1.373(3) . ?
C1 C2 1.415(3) . ?
C1 C7 1.482(3) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.360(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(4) . ?
C5 H5 0.9300 . ?
C6 Cl1 1.720(3) . ?
C7 C8 1.364(3) . ?
C7 C11 1.431(3) . ?
C8 C9 1.398(3) . ?
C8 C17 1.499(3) . ?
C9 C10 1.385(3) . ?
C9 C16 1.458(3) . ?
C10 N1 1.384(3) . ?
C10 C15 1.417(3) . ?
C11 O1 1.218(3) . ?
C11 N1 1.462(2) . ?
C12 C13 1.347(3) . ?
C12 N1 1.380(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.391(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.346(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 O2 1.211(2) . ?
C16 N2 1.405(3) . ?
C17 O3 1.201(3) . ?
C17 N2 1.386(3) . ?
C18 N2 1.452(3) . ?
C18 C19 1.510(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.374(3) . ?
C19 C24 1.384(3) . ?
C20 C21 1.392(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.368(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.371(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.378(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

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
C6 C1 C2 118.7(2) . . ?
C6 C1 C7 121.64(19) . . ?
C2 C1 C7 119.70(19) . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 121.4(2) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 118.6(3) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 121.7(2) . . ?
C1 C6 Cl1 118.87(18) . . ?
C5 C6 Cl1 119.5(2) . . ?
C8 C7 C11 118.63(17) . . ?
C8 C7 C1 123.41(18) . . ?
C11 C7 C1 117.96(17) . . ?
C7 C8 C9 123.67(18) . . ?
C7 C8 C17 129.00(17) . . ?
C9 C8 C17 107.31(16) . . ?
C10 C9 C8 120.76(18) . . ?
C10 C9 C16 130.14(18) . . ?
C8 C9 C16 109.04(17) . . ?
N1 C10 C9 117.12(17) . . ?
N1 C10 C15 117.97(19) . . ?
C9 C10 C15 124.9(2) . . ?
O1 C11 C7 126.27(18) . . ?
O1 C11 N1 117.60(18) . . ?
C7 C11 N1 116.13(17) . . ?
C13 C12 N1 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
N1 C12 H12 119.6 . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 120.7(2) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
O2 C16 N2 123.9(2) . . ?
O2 C16 C9 130.4(2) . . ?
N2 C16 C9 105.72(17) . . ?
O3 C17 N2 125.2(2) . . ?
O3 C17 C8 129.44(19) . . ?
N2 C17 C8 105.37(17) . . ?
N2 C18 C19 114.08(18) . . ?
N2 C18 H18A 108.7 . . ?
C19 C18 H18A 108.7 . . ?
N2 C18 H18B 108.7 . . ?
C19 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 C24 118.7(2) . . ?
C20 C19 C18 122.9(2) . . ?
C24 C19 C18 118.4(2) . . ?
C19 C20 C21 120.2(2) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 120.3(2) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 119.9(2) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C24 119.9(2) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C19 121.0(2) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
C12 N1 C10 120.19(18) . . ?
C12 N1 C11 116.15(18) . . ?
C10 N1 C11 123.66(16) . . ?
C17 N2 C16 112.53(17) . . ?
C17 N2 C18 123.11(19) . . ?
C16 N2 C18 124.34(18) . . ?

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
C6 C1 C2 C3 0.0(3) . . . . ?
C7 C1 C2 C3 -179.6(2) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C2 C3 C4 C5 1.3(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
C7 C1 C6 C5 -179.3(2) . . . . ?
C2 C1 C6 Cl1 -178.92(17) . . . . ?
C7 C1 C6 Cl1 0.7(3) . . . . ?
C4 C5 C6 C1 -1.0(4) . . . . ?
C4 C5 C6 Cl1 179.0(2) . . . . ?
C6 C1 C7 C8 94.5(3) . . . . ?
C2 C1 C7 C8 -86.0(3) . . . . ?
C6 C1 C7 C11 -85.3(3) . . . . ?
C2 C1 C7 C11 94.3(2) . . . . ?
C11 C7 C8 C9 -1.4(3) . . . . ?
C1 C7 C8 C9 178.87(18) . . . . ?
C11 C7 C8 C17 176.75(18) . . . . ?
C1 C7 C8 C17 -3.0(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C17 C8 C9 C10 -178.59(17) . . . . ?
C7 C8 C9 C16 177.48(18) . . . . ?
C17 C8 C9 C16 -1.0(2) . . . . ?
C8 C9 C10 N1 0.6(3) . . . . ?
C16 C9 C10 N1 -176.40(18) . . . . ?
C8 C9 C10 C15 -179.89(19) . . . . ?
C16 C9 C10 C15 3.1(3) . . . . ?
C8 C7 C11 O1 -177.6(2) . . . . ?
C1 C7 C11 O1 2.1(3) . . . . ?
C8 C7 C11 N1 2.2(3) . . . . ?
C1 C7 C11 N1 -178.03(16) . . . . ?
N1 C12 C13 C14 -0.1(4) . . . . ?
C12 C13 C14 C15 0.5(5) . . . . ?
C13 C14 C15 C10 -0.2(4) . . . . ?
N1 C10 C15 C14 -0.3(3) . . . . ?
C9 C10 C15 C14 -179.8(2) . . . . ?
C10 C9 C16 O2 -2.3(4) . . . . ?
C8 C9 C16 O2 -179.6(2) . . . . ?
C10 C9 C16 N2 177.59(19) . . . . ?
C8 C9 C16 N2 0.3(2) . . . . ?
C7 C8 C17 O3 2.5(4) . . . . ?
C9 C8 C17 O3 -179.1(2) . . . . ?
C7 C8 C17 N2 -177.04(19) . . . . ?
C9 C8 C17 N2 1.3(2) . . . . ?
N2 C18 C19 C20 -26.3(3) . . . . ?
N2 C18 C19 C24 154.4(2) . . . . ?
C24 C19 C20 C21 0.3(3) . . . . ?
C18 C19 C20 C21 -178.9(2) . . . . ?
C19 C20 C21 C22 0.2(4) . . . . ?
C20 C21 C22 C23 -0.7(4) . . . . ?
C21 C22 C23 C24 0.7(4) . . . . ?
C22 C23 C24 C19 -0.1(4) . . . . ?
C20 C19 C24 C23 -0.4(4) . . . . ?
C18 C19 C24 C23 178.9(2) . . . . ?
C13 C12 N1 C10 -0.5(4) . . . . ?
C13 C12 N1 C11 179.4(2) . . . . ?
C9 C10 N1 C12 -179.79(19) . . . . ?
C15 C10 N1 C12 0.7(3) . . . . ?
C9 C10 N1 C11 0.4(3) . . . . ?
C15 C10 N1 C11 -179.15(18) . . . . ?
O1 C11 N1 C12 -1.8(3) . . . . ?
C7 C11 N1 C12 178.38(19) . . . . ?
O1 C11 N1 C10 178.07(19) . . . . ?
C7 C11 N1 C10 -1.8(3) . . . . ?
O3 C17 N2 C16 179.2(2) . . . . ?
C8 C17 N2 C16 -1.2(2) . . . . ?
O3 C17 N2 C18 0.7(3) . . . . ?
C8 C17 N2 C18 -179.71(18) . . . . ?
O2 C16 N2 C17 -179.5(2) . . . . ?
C9 C16 N2 C17 0.6(2) . . . . ?
O2 C16 N2 C18 -1.0(3) . . . . ?
C9 C16 N2 C18 179.10(19) . . . . ?
C19 C18 N2 C17 -74.1(3) . . . . ?
C19 C18 N2 C16 107.5(2) . . . . ?

_refine_diff_density_max         0.648
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.050



