# Supplementary Information (SI) for Chemical Science.
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2384389'
loop_
_audit_author_name
_audit_author_address
'Sheng xiang Gao'
;Jilin University
China
;
_audit_update_record             
;
2024-09-16 deposited with the CCDC.	2025-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H10 Cl10 N'
_chemical_formula_weight         678.84

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'
Cl Cl 0.1484 0.1585 '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'

_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                   8.3050(15)
_cell_length_b                   8.8068(17)
_cell_length_c                   19.111(4)
_cell_angle_alpha                97.232(7)
_cell_angle_beta                 96.934(7)
_cell_angle_gamma                95.160(7)
_cell_volume                     1368.7(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    9851
_cell_measurement_theta_min      2.575
_cell_measurement_theta_max      27.335

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_F_000             674
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.037
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44359
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.345
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6268
_reflns_number_gt                5052
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0460P)²+2.2003P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6268
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1431
_refine_ls_wR_factor_gt          0.1316
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.001
_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
Cl1 Cl -0.19559(11) 1.08227(11) 0.20136(5) 0.0535(2) Uani 1 1 d . . . . .
Cl5 Cl 0.13699(13) 0.58175(11) 0.22876(6) 0.0630(3) Uani 1 1 d . . . . .
Cl6 Cl -0.13207(10) 0.89365(13) 0.36572(5) 0.0567(3) Uani 1 1 d . . . . .
Cl8 Cl 0.47508(10) 0.89348(13) 0.28432(5) 0.0569(3) Uani 1 1 d . . . . .
Cl10 Cl 0.13279(15) 1.35144(13) 0.01730(6) 0.0676(3) Uani 1 1 d . . . . .
Cl11 Cl 0.37581(16) 0.79075(14) 0.54580(5) 0.0742(3) Uani 1 1 d . . . . .
Cl15 Cl 0.30856(17) 0.77721(15) -0.00550(6) 0.0755(3) Uani 1 1 d . . . . .
Cl16 Cl -0.48310(14) 0.51588(16) 0.10632(7) 0.0797(4) Uani 1 1 d . . . . .
Cl17 Cl 0.64237(16) 1.48508(16) 0.31282(7) 0.0840(4) Uani 1 1 d . . . . .
Cl2 Cl 0.1341(2) 1.41528(16) 0.45763(8) 0.1094(6) Uani 1 1 d . . . . .
N3 N 0.1748(3) 1.0540(3) 0.23075(12) 0.0329(5) Uani 1 1 d . . . . .
C4 C 0.1742(3) 0.8934(3) 0.32701(15) 0.0306(6) Uani 1 1 d . . . . .
C6 C -0.0327(3) 0.8286(4) 0.21446(14) 0.0324(6) Uani 1 1 d . . . . .
C9 C 0.1072(3) 0.9255(3) 0.25631(15) 0.0322(6) Uani 1 1 d . . . . .
C11 C -0.0366(4) 0.6678(4) 0.20233(16) 0.0388(7) Uani 1 1 d . . . . .
C12 C 0.3789(5) 1.4384(4) 0.37853(19) 0.0537(9) Uani 1 1 d . . . . .
H12 H 0.424999 1.521790 0.411882 0.064 Uiso 1 1 calc R U . . .
C15 C 0.0748(4) 0.8729(4) 0.38069(16) 0.0362(6) Uani 1 1 d . . . . .
C17 C 0.2297(4) 0.9257(4) 0.11630(17) 0.0397(7) Uani 1 1 d . . . . .
H17 H 0.249189 0.837047 0.136353 0.048 Uiso 1 1 calc R U . . .
C19 C -0.1773(4) 0.8868(4) 0.18708(15) 0.0372(7) Uani 1 1 d . . . . .
C20 C 0.1859(4) 1.0537(4) 0.15675(15) 0.0343(6) Uani 1 1 d . . . . .
C25 C 0.2410(4) 1.1871(3) 0.27908(15) 0.0350(6) Uani 1 1 d . . . . .
C28 C 0.4046(4) 0.8513(4) 0.41297(18) 0.0445(8) Uani 1 1 d . . . . .
H28 H 0.515639 0.844402 0.423915 0.053 Uiso 1 1 calc R U . . .
C30 C 0.1550(4) 1.1853(4) 0.12646(16) 0.0404(7) Uani 1 1 d . . . . .
H30 H 0.124369 1.270643 0.153527 0.048 Uiso 1 1 calc R U . . .
C32 C -0.1725(4) 0.5711(4) 0.16832(18) 0.0473(8) Uani 1 1 d . . . . .
H32 H -0.170414 0.464870 0.161485 0.057 Uiso 1 1 calc R U . . .
C33 C -0.3138(4) 0.7920(4) 0.15263(17) 0.0438(8) Uani 1 1 d . . . . .
H33 H -0.406611 0.834067 0.134935 0.053 Uiso 1 1 calc R U . . .
C34 C 0.1599(4) 1.2364(4) 0.33606(18) 0.0440(8) Uani 1 1 d . . . . .
H34 H 0.058786 1.187297 0.340958 0.053 Uiso 1 1 calc R U . . .
C35 C 0.2149(5) 1.0622(5) 0.01332(18) 0.0513(9) Uani 1 1 d . . . . .
H35 H 0.224740 1.064812 -0.034479 0.062 Uiso 1 1 calc R U . . .
C38 C 0.3407(4) 0.8807(4) 0.34656(17) 0.0368(6) Uani 1 1 d . . . . .
C39 C 0.1350(4) 0.8420(4) 0.44775(17) 0.0454(8) Uani 1 1 d . . . . .
H39 H 0.065798 0.828344 0.481751 0.054 Uiso 1 1 calc R U . . .
C40 C 0.1706(4) 1.1871(4) 0.05519(17) 0.0439(8) Uani 1 1 d . . . . .
C43 C -0.3099(4) 0.6358(5) 0.14508(18) 0.0487(9) Uani 1 1 d . . . . .
C47 C 0.2999(5) 0.8322(4) 0.46276(17) 0.0467(8) Uani 1 1 d . . . . .
C50 C 0.3900(4) 1.2651(4) 0.27100(17) 0.0421(7) Uani 1 1 d . . . . .
H50 H 0.444522 1.233730 0.232827 0.050 Uiso 1 1 calc R U . . .
C51 C 0.2439(4) 0.9331(4) 0.04517(18) 0.0471(8) Uani 1 1 d . . . . .
C52 C 0.4549(5) 1.3896(4) 0.32065(18) 0.0472(8) Uani 1 1 d . . . . .
C53 C 0.2321(5) 1.3589(4) 0.3850(2) 0.0539(9) 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
Cl1 C19 1.732(4) . ?
Cl5 C11 1.739(3) . ?
Cl6 C15 1.737(3) . ?
Cl8 C38 1.733(3) . ?
Cl10 C40 1.734(4) . ?
Cl11 C47 1.731(3) . ?
Cl15 C51 1.742(4) . ?
Cl16 C43 1.734(3) . ?
Cl17 C52 1.734(4) . ?
Cl2 C53 1.734(4) . ?
N3 C9 1.388(4) . ?
N3 C25 1.421(4) . ?
N3 C20 1.428(4) . ?
C4 C38 1.407(4) . ?
C4 C15 1.411(4) . ?
C4 C9 1.469(4) . ?
C6 C11 1.402(4) . ?
C6 C19 1.416(4) . ?
C6 C9 1.464(4) . ?
C11 C32 1.391(4) . ?
C12 C53 1.377(6) . ?
C12 C52 1.380(5) . ?
C12 H12 0.9300 . ?
C15 C39 1.387(4) . ?
C17 C20 1.387(4) . ?
C17 C51 1.388(5) . ?
C17 H17 0.9300 . ?
C19 C33 1.388(5) . ?
C20 C30 1.390(4) . ?
C25 C34 1.392(4) . ?
C25 C50 1.395(4) . ?
C28 C47 1.380(5) . ?
C28 C38 1.380(4) . ?
C28 H28 0.9300 . ?
C30 C40 1.386(4) . ?
C30 H30 0.9300 . ?
C32 C43 1.372(5) . ?
C32 H32 0.9300 . ?
C33 C43 1.369(5) . ?
C33 H33 0.9300 . ?
C34 C53 1.376(5) . ?
C34 H34 0.9300 . ?
C35 C51 1.381(5) . ?
C35 C40 1.382(5) . ?
C35 H35 0.9300 . ?
C39 C47 1.377(5) . ?
C39 H39 0.9300 . ?
C50 C52 1.379(5) . ?
C50 H50 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
C9 N3 C25 119.8(2) . . ?
C9 N3 C20 121.4(2) . . ?
C25 N3 C20 118.8(2) . . ?
C38 C4 C15 114.9(3) . . ?
C38 C4 C9 123.1(3) . . ?
C15 C4 C9 122.0(3) . . ?
C11 C6 C19 114.8(3) . . ?
C11 C6 C9 121.6(3) . . ?
C19 C6 C9 123.5(3) . . ?
N3 C9 C6 120.1(3) . . ?
N3 C9 C4 118.7(2) . . ?
C6 C9 C4 121.2(2) . . ?
C32 C11 C6 123.4(3) . . ?
C32 C11 Cl5 117.1(3) . . ?
C6 C11 Cl5 119.5(2) . . ?
C53 C12 C52 117.4(3) . . ?
C53 C12 H12 121.3 . . ?
C52 C12 H12 121.3 . . ?
C39 C15 C4 123.1(3) . . ?
C39 C15 Cl6 116.7(2) . . ?
C4 C15 Cl6 120.1(2) . . ?
C20 C17 C51 118.3(3) . . ?
C20 C17 H17 120.8 . . ?
C51 C17 H17 120.8 . . ?
C33 C19 C6 122.7(3) . . ?
C33 C19 Cl1 116.8(3) . . ?
C6 C19 Cl1 120.4(2) . . ?
C17 C20 C30 120.7(3) . . ?
C17 C20 N3 120.6(3) . . ?
C30 C20 N3 118.7(3) . . ?
C34 C25 C50 120.0(3) . . ?
C34 C25 N3 119.9(3) . . ?
C50 C25 N3 120.1(3) . . ?
C47 C28 C38 118.5(3) . . ?
C47 C28 H28 120.8 . . ?
C38 C28 H28 120.8 . . ?
C40 C30 C20 118.8(3) . . ?
C40 C30 H30 120.6 . . ?
C20 C30 H30 120.6 . . ?
C43 C32 C11 118.5(3) . . ?
C43 C32 H32 120.8 . . ?
C11 C32 H32 120.8 . . ?
C43 C33 C19 119.0(3) . . ?
C43 C33 H33 120.5 . . ?
C19 C33 H33 120.5 . . ?
C53 C34 C25 118.8(3) . . ?
C53 C34 H34 120.6 . . ?
C25 C34 H34 120.6 . . ?
C51 C35 C40 117.5(3) . . ?
C51 C35 H35 121.3 . . ?
C40 C35 H35 121.3 . . ?
C28 C38 C4 123.4(3) . . ?
C28 C38 Cl8 116.8(2) . . ?
C4 C38 Cl8 119.8(2) . . ?
C47 C39 C15 118.4(3) . . ?
C47 C39 H39 120.8 . . ?
C15 C39 H39 120.8 . . ?
C35 C40 C30 122.1(3) . . ?
C35 C40 Cl10 119.0(3) . . ?
C30 C40 Cl10 118.9(3) . . ?
C33 C43 C32 121.7(3) . . ?
C33 C43 Cl16 119.5(3) . . ?
C32 C43 Cl16 118.8(3) . . ?
C39 C47 C28 121.7(3) . . ?
C39 C47 Cl11 118.8(3) . . ?
C28 C47 Cl11 119.5(3) . . ?
C52 C50 C25 118.8(3) . . ?
C52 C50 H50 120.6 . . ?
C25 C50 H50 120.6 . . ?
C35 C51 C17 122.6(3) . . ?
C35 C51 Cl15 118.3(3) . . ?
C17 C51 Cl15 119.1(3) . . ?
C50 C52 C12 122.4(3) . . ?
C50 C52 Cl17 119.5(3) . . ?
C12 C52 Cl17 118.1(3) . . ?
C34 C53 C12 122.6(3) . . ?
C34 C53 Cl2 118.6(3) . . ?
C12 C53 Cl2 118.8(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
C25 N3 C9 C6 146.0(3) . . . . ?
C20 N3 C9 C6 -36.7(4) . . . . ?
C25 N3 C9 C4 -31.3(4) . . . . ?
C20 N3 C9 C4 146.0(3) . . . . ?
C11 C6 C9 N3 132.1(3) . . . . ?
C19 C6 C9 N3 -52.0(4) . . . . ?
C11 C6 C9 C4 -50.7(4) . . . . ?
C19 C6 C9 C4 125.2(3) . . . . ?
C38 C4 C9 N3 -54.2(4) . . . . ?
C15 C4 C9 N3 125.9(3) . . . . ?
C38 C4 C9 C6 128.5(3) . . . . ?
C15 C4 C9 C6 -51.4(4) . . . . ?
C19 C6 C11 C32 -2.1(4) . . . . ?
C9 C6 C11 C32 174.2(3) . . . . ?
C19 C6 C11 Cl5 176.4(2) . . . . ?
C9 C6 C11 Cl5 -7.3(4) . . . . ?
C38 C4 C15 C39 -0.2(5) . . . . ?
C9 C4 C15 C39 179.8(3) . . . . ?
C38 C4 C15 Cl6 177.1(2) . . . . ?
C9 C4 C15 Cl6 -2.9(4) . . . . ?
C11 C6 C19 C33 1.7(4) . . . . ?
C9 C6 C19 C33 -174.5(3) . . . . ?
C11 C6 C19 Cl1 176.9(2) . . . . ?
C9 C6 C19 Cl1 0.7(4) . . . . ?
C51 C17 C20 C30 0.8(5) . . . . ?
C51 C17 C20 N3 -177.9(3) . . . . ?
C9 N3 C20 C17 -40.8(4) . . . . ?
C25 N3 C20 C17 136.6(3) . . . . ?
C9 N3 C20 C30 140.5(3) . . . . ?
C25 N3 C20 C30 -42.2(4) . . . . ?
C9 N3 C25 C34 -41.3(4) . . . . ?
C20 N3 C25 C34 141.3(3) . . . . ?
C9 N3 C25 C50 136.4(3) . . . . ?
C20 N3 C25 C50 -41.0(4) . . . . ?
C17 C20 C30 C40 -0.7(5) . . . . ?
N3 C20 C30 C40 178.0(3) . . . . ?
C6 C11 C32 C43 0.3(5) . . . . ?
Cl5 C11 C32 C43 -178.2(3) . . . . ?
C6 C19 C33 C43 0.5(5) . . . . ?
Cl1 C19 C33 C43 -174.9(2) . . . . ?
C50 C25 C34 C53 -2.2(5) . . . . ?
N3 C25 C34 C53 175.4(3) . . . . ?
C47 C28 C38 C4 0.4(5) . . . . ?
C47 C28 C38 Cl8 -176.6(3) . . . . ?
C15 C4 C38 C28 -0.3(5) . . . . ?
C9 C4 C38 C28 179.7(3) . . . . ?
C15 C4 C38 Cl8 176.7(2) . . . . ?
C9 C4 C38 Cl8 -3.3(4) . . . . ?
C4 C15 C39 C47 0.5(5) . . . . ?
Cl6 C15 C39 C47 -176.9(3) . . . . ?
C51 C35 C40 C30 -0.1(5) . . . . ?
C51 C35 C40 Cl10 -179.9(3) . . . . ?
C20 C30 C40 C35 0.4(5) . . . . ?
C20 C30 C40 Cl10 -179.8(2) . . . . ?
C19 C33 C43 C32 -2.5(5) . . . . ?
C19 C33 C43 Cl16 176.6(2) . . . . ?
C11 C32 C43 C33 2.1(5) . . . . ?
C11 C32 C43 Cl16 -177.0(3) . . . . ?
C15 C39 C47 C28 -0.4(5) . . . . ?
C15 C39 C47 Cl11 -179.0(3) . . . . ?
C38 C28 C47 C39 -0.1(5) . . . . ?
C38 C28 C47 Cl11 178.5(3) . . . . ?
C34 C25 C50 C52 0.7(5) . . . . ?
N3 C25 C50 C52 -177.0(3) . . . . ?
C40 C35 C51 C17 0.2(5) . . . . ?
C40 C35 C51 Cl15 -177.2(3) . . . . ?
C20 C17 C51 C35 -0.5(5) . . . . ?
C20 C17 C51 Cl15 176.9(2) . . . . ?
C25 C50 C52 C12 0.9(5) . . . . ?
C25 C50 C52 Cl17 178.4(3) . . . . ?
C53 C12 C52 C50 -0.9(6) . . . . ?
C53 C12 C52 Cl17 -178.4(3) . . . . ?
C25 C34 C53 C12 2.3(6) . . . . ?
C25 C34 C53 Cl2 -177.6(3) . . . . ?
C52 C12 C53 C34 -0.8(6) . . . . ?
C52 C12 C53 Cl2 179.2(3) . . . . ?

_refine_diff_density_max         0.577
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.111



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_mo
_database_code_depnum_ccdc_archive 'CCDC 2384400'
loop_
_audit_author_name
_audit_author_address
'Sheng xiang Gao'
;Jilin University
China
;
_audit_update_record             
;
2024-09-16 deposited with the CCDC.	2025-01-30 downloaded from the CCDC.
;
_audit_creation_date             2024-06-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        2PhN-BTM
_chemical_formula_moiety         'C25 H14 Cl6 N'
_chemical_formula_sum            'C25 H14 Cl6 N'
_chemical_formula_weight         541.07
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.4717(16)
_cell_length_b                   8.3566(9)
_cell_length_c                   17.0028(18)
_cell_angle_alpha                90
_cell_angle_beta                 103.423(4)
_cell_angle_gamma                90
_cell_volume                     2276.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9595
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      27.521
_cell_measurement_theta_min      2.731
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  27.521
_exptl_absorpt_correction_T_min  2.731
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            64972
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_min         2.496
_diffrn_ambient_temperature      125.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4808
_reflns_number_total             5228
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0248
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0203P)²+1.7507P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0577
_refine_ls_wR_factor_ref         0.0595
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14),
 C16(H16), C19(H19), C22(H22), C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
Cl1 Cl 0.10702(2) 0.92071(4) 0.32731(2) 0.02039(8) Uani 1 1 d . . . . .
Cl2 Cl 0.29312(2) 0.93805(4) 0.24791(2) 0.02163(8) Uani 1 1 d . . . . .
Cl3 Cl 0.25859(2) 0.60787(4) 0.51462(2) 0.02252(8) Uani 1 1 d . . . . .
Cl4 Cl -0.09382(2) 0.47900(4) 0.40724(2) 0.02531(8) Uani 1 1 d . . . . .
Cl5 Cl 0.19381(2) 0.28688(4) 0.34589(2) 0.02465(8) Uani 1 1 d . . . . .
Cl6 Cl 0.42752(2) 1.15923(5) 0.54561(2) 0.02893(9) Uani 1 1 d . . . . .
C0AA C 0.36181(8) 0.54535(16) 0.30270(8) 0.0160(3) Uani 1 1 d . . . . .
C2 C 0.28096(8) 0.77385(15) 0.38281(8) 0.0147(2) Uani 1 1 d . . . . .
C3 C 0.29492(8) 0.76902(16) 0.46764(8) 0.0166(3) Uani 1 1 d . . . . .
N1 N 0.27317(7) 0.57017(13) 0.27859(7) 0.0152(2) Uani 1 1 d . . . . .
C5 C 0.01428(8) 0.68473(16) 0.36450(8) 0.0181(3) Uani 1 1 d . . . . .
H5 H -0.024074 0.767069 0.369202 0.022 Uiso 1 1 calc R . . . .
C6 C 0.41267(9) 0.60043(19) 0.25361(8) 0.0227(3) Uani 1 1 d . . . . .
H6 H 0.388880 0.656121 0.205016 0.027 Uiso 1 1 calc R . . . .
C7 C 0.15021(8) 0.60386(16) 0.33920(8) 0.0148(2) Uani 1 1 d . . . . .
C8 C 0.33878(9) 0.88612(18) 0.51765(8) 0.0203(3) Uani 1 1 d . . . . .
H8 H 0.345861 0.879641 0.574619 0.024 Uiso 1 1 calc R . . . .
C9 C 0.48268(9) 0.44124(18) 0.39657(9) 0.0225(3) Uani 1 1 d . . . . .
H9 H 0.506783 0.387451 0.445659 0.027 Uiso 1 1 calc R . . . .
C10 C 0.36075(8) 1.02552(16) 0.40000(8) 0.0174(3) Uani 1 1 d . . . . .
H10 H 0.383767 1.112808 0.376699 0.021 Uiso 1 1 calc R . . . .
C11 C 0.39673(9) 0.46706(17) 0.37507(8) 0.0190(3) Uani 1 1 d . . . . .
H11 H 0.362319 0.431683 0.409382 0.023 Uiso 1 1 calc R . . . .
C12 C 0.16033(9) 0.60046(17) 0.15784(9) 0.0208(3) Uani 1 1 d . . . . .
H12 H 0.140554 0.691417 0.181250 0.025 Uiso 1 1 calc R . . . .
C13 C 0.31502(8) 0.90790(16) 0.35187(8) 0.0160(3) Uani 1 1 d . . . . .
C14 C 0.25798(9) 0.38175(17) 0.16615(9) 0.0199(3) Uani 1 1 d . . . . .
H14 H 0.304728 0.323277 0.195503 0.024 Uiso 1 1 calc R . . . .
C15 C -0.00351(8) 0.52600(17) 0.37655(8) 0.0179(3) Uani 1 1 d . . . . .
C16 C 0.05024(8) 0.40437(16) 0.36627(8) 0.0177(3) Uani 1 1 d . . . . .
H16 H 0.035692 0.295504 0.371434 0.021 Uiso 1 1 calc R . . . .
C17 C 0.08971(8) 0.72027(16) 0.34536(8) 0.0161(3) Uani 1 1 d . . . . .
C18 C 0.12546(8) 0.44417(16) 0.34835(8) 0.0165(3) Uani 1 1 d . . . . .
C19 C 0.12000(10) 0.54993(19) 0.08066(9) 0.0257(3) Uani 1 1 d . . . . .
H19 H 0.072649 0.606989 0.051448 0.031 Uiso 1 1 calc R . . . .
C20 C 0.22992(8) 0.51682(16) 0.20061(8) 0.0158(3) Uani 1 1 d . . . . .
C21 C 0.37204(9) 1.01242(17) 0.48326(8) 0.0193(3) Uani 1 1 d . . . . .
C22 C 0.21732(10) 0.33337(18) 0.08894(9) 0.0247(3) Uani 1 1 d . . . . .
H22 H 0.236867 0.242401 0.065342 0.030 Uiso 1 1 calc R . . . .
C23 C 0.23371(8) 0.64875(16) 0.33106(8) 0.0170(3) Uani 1 1 d . . . . .
C24 C 0.14826(10) 0.41695(19) 0.04590(9) 0.0267(3) Uani 1 1 d . . . . .
H24 H 0.120590 0.383381 -0.006901 0.032 Uiso 1 1 calc R . . . .
C25 C 0.49827(9) 0.5740(2) 0.27562(9) 0.0278(3) Uani 1 1 d . . . . .
H25 H 0.532892 0.611199 0.241890 0.033 Uiso 1 1 calc R . . . .
C26 C 0.53330(9) 0.4933(2) 0.34694(9) 0.0256(3) Uani 1 1 d . . . . .
H26 H 0.591706 0.473965 0.361626 0.031 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 C17 1.7382(14) . ?
Cl2 C13 1.7383(13) . ?
Cl3 C3 1.7412(14) . ?
Cl4 C15 1.7319(14) . ?
Cl5 C18 1.7374(14) . ?
Cl6 C21 1.7362(14) . ?
C0AA N1 1.4369(17) . ?
C0AA C6 1.391(2) . ?
C0AA C11 1.3945(19) . ?
C2 C3 1.4075(18) . ?
C2 C13 1.4084(18) . ?
C2 C23 1.4679(18) . ?
C3 C8 1.3847(19) . ?
N1 C20 1.4233(17) . ?
N1 C23 1.3852(17) . ?
C5 C15 1.3839(19) . ?
C5 C17 1.3876(19) . ?
C6 C25 1.390(2) . ?
C7 C17 1.4138(18) . ?
C7 C18 1.4144(18) . ?
C7 C23 1.4630(18) . ?
C8 C21 1.380(2) . ?
C9 C11 1.394(2) . ?
C9 C26 1.387(2) . ?
C10 C13 1.3845(18) . ?
C10 C21 1.3887(19) . ?
C12 C19 1.392(2) . ?
C12 C20 1.3944(19) . ?
C14 C20 1.3987(19) . ?
C14 C22 1.388(2) . ?
C15 C16 1.3854(19) . ?
C16 C18 1.3835(19) . ?
C19 C24 1.389(2) . ?
C22 C24 1.390(2) . ?
C25 C26 1.390(2) . ?

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 C0AA N1 119.64(12) . . ?
C6 C0AA C11 120.14(13) . . ?
C11 C0AA N1 120.21(12) . . ?
C3 C2 C13 114.90(12) . . ?
C3 C2 C23 122.12(12) . . ?
C13 C2 C23 122.98(12) . . ?
C2 C3 Cl3 120.04(10) . . ?
C8 C3 Cl3 116.80(10) . . ?
C8 C3 C2 123.15(13) . . ?
C20 N1 C0AA 118.44(11) . . ?
C23 N1 C0AA 118.83(11) . . ?
C23 N1 C20 122.70(11) . . ?
C15 C5 C17 118.15(13) . . ?
C25 C6 C0AA 120.04(14) . . ?
C17 C7 C18 114.52(12) . . ?
C17 C7 C23 121.66(12) . . ?
C18 C7 C23 123.62(12) . . ?
C21 C8 C3 118.83(13) . . ?
C26 C9 C11 120.61(14) . . ?
C13 C10 C21 118.18(13) . . ?
C9 C11 C0AA 119.32(13) . . ?
C19 C12 C20 119.62(14) . . ?
C2 C13 Cl2 119.24(10) . . ?
C10 C13 Cl2 117.01(10) . . ?
C10 C13 C2 123.58(12) . . ?
C22 C14 C20 119.83(14) . . ?
C5 C15 Cl4 119.22(11) . . ?
C5 C15 C16 121.40(13) . . ?
C16 C15 Cl4 119.36(11) . . ?
C18 C16 C15 118.86(13) . . ?
C5 C17 Cl1 116.11(10) . . ?
C5 C17 C7 123.71(12) . . ?
C7 C17 Cl1 120.18(10) . . ?
C7 C18 Cl5 120.41(10) . . ?
C16 C18 Cl5 116.22(10) . . ?
C16 C18 C7 123.15(12) . . ?
C24 C19 C12 120.68(14) . . ?
C12 C20 N1 120.13(12) . . ?
C12 C20 C14 119.84(13) . . ?
C14 C20 N1 120.03(12) . . ?
C8 C21 Cl6 119.09(11) . . ?
C8 C21 C10 121.32(13) . . ?
C10 C21 Cl6 119.58(11) . . ?
C14 C22 C24 120.52(14) . . ?
N1 C23 C2 117.45(11) . . ?
N1 C23 C7 122.10(12) . . ?
C7 C23 C2 120.34(11) . . ?
C19 C24 C22 119.50(14) . . ?
C6 C25 C26 120.10(14) . . ?
C9 C26 C25 119.76(14) . . ?


_olex2_exptl_crystal_mounting_method no
_olex2_submission_original_sample_id 2PhN-BTM
_olex2_submission_special_instructions 'No special instructions were received'
