# 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. 
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data_230325lu_ngy_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2297777'
loop_
_audit_author_name
_audit_author_address
You
;HFUT
China
;
_audit_update_record             
;
2023-09-27 deposited with the CCDC.	2024-02-23 downloaded from the CCDC.
;
_audit_creation_date             2023-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 Cl3 N O2'
_chemical_formula_sum            'C23 H18 Cl3 N O2'
_chemical_formula_weight         446.73
_chemical_absolute_configuration ad
_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'
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'
O O 0.0106 0.0060 '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      orthorhombic
_space_group_IT_number           19
_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.5787(5)
_cell_length_b                   13.2751(9)
_cell_length_c                   27.4431(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2032.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6508
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.70
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.471
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6634
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1590 before and 0.0712 after correction.
The Ratio of minimum to maximum transmission is 0.8898.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            19100
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.520
_diffrn_reflns_theta_min         1.704
_diffrn_ambient_temperature      193.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4095
_reflns_number_total             4684
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 1481 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4684
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.084
_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)+(0.0185P)²+0.7909P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0775
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C13(H13), C14(H14), C15(H15), C5(H5), C16(H16), C22(H22), C1(H1A),
 C19(H19), C21(H21), C4(H4), C3(H3), C20(H20), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Cl2 Cl 0.27388(17) 0.18346(6) 0.57156(3) 0.0314(2) Uani 1 1 d . . . . .
Cl3 Cl -0.12500(16) 0.32064(7) 0.57152(3) 0.0330(2) Uani 1 1 d . . . . .
Cl1 Cl 0.32661(17) 0.38097(7) 0.53072(3) 0.0327(2) Uani 1 1 d . . . . .
O2 O 0.2778(4) 0.62250(15) 0.63547(8) 0.0265(5) Uani 1 1 d . . . . .
O1 O 0.5903(5) 0.51443(17) 0.64051(10) 0.0330(6) Uani 1 1 d . . . . .
N1 N 0.2074(6) 0.45843(18) 0.63145(10) 0.0263(6) Uani 1 1 d . . . . .
H1 H 0.055292 0.475890 0.630524 0.032 Uiso 1 1 calc R . . . .
C9 C 0.3785(7) 0.5298(2) 0.63611(12) 0.0244(7) Uani 1 1 d . . . . .
C6 C 0.1941(6) 0.2910(2) 0.67156(11) 0.0220(7) Uani 1 1 d . . . . .
C18 C 0.5506(7) 0.9428(2) 0.60808(11) 0.0223(7) Uani 1 1 d . . . . .
C13 C 0.0565(6) 0.7924(2) 0.56089(12) 0.0268(8) Uani 1 1 d . . . . .
H13 H -0.041133 0.739806 0.573420 0.032 Uiso 1 1 calc R . . . .
C17 C 0.3797(6) 0.9109(2) 0.57016(11) 0.0218(7) Uani 1 1 d . . . . .
C23 C 0.5086(6) 0.8842(2) 0.64970(11) 0.0229(7) Uani 1 1 d . . . . .
C7 C 0.2741(6) 0.3531(2) 0.62798(11) 0.0211(7) Uani 1 1 d . . . . .
H7 H 0.453251 0.350867 0.627587 0.025 Uiso 1 1 calc R . . . .
C12 C 0.2394(6) 0.8324(2) 0.58840(11) 0.0217(7) Uani 1 1 d . . . . .
C14 C 0.0177(7) 0.8305(3) 0.51428(12) 0.0332(8) Uani 1 1 d . . . . .
H14 H -0.109009 0.804273 0.494952 0.040 Uiso 1 1 calc R . . . .
C15 C 0.1616(8) 0.9062(2) 0.49588(12) 0.0326(9) Uani 1 1 d . . . . .
H15 H 0.134622 0.930319 0.463749 0.039 Uiso 1 1 calc R . . . .
C5 C -0.0190(6) 0.3098(3) 0.69578(11) 0.0270(8) Uani 1 1 d . . . . .
H5 H -0.122759 0.361713 0.684708 0.032 Uiso 1 1 calc R . . . .
C16 C 0.3438(8) 0.9473(2) 0.52338(12) 0.0290(8) Uani 1 1 d . . . . .
H16 H 0.442328 0.999354 0.510593 0.035 Uiso 1 1 calc R . . . .
C22 C 0.6435(7) 0.8988(2) 0.69130(12) 0.0297(8) Uani 1 1 d . . . . .
H22 H 0.615713 0.859094 0.719549 0.036 Uiso 1 1 calc R . . . .
C11 C 0.3200(6) 0.8046(2) 0.63942(10) 0.0215(7) Uani 1 1 d . . . . .
H11 H 0.184533 0.808485 0.663222 0.026 Uiso 1 1 calc R . . . .
C1 C 0.3432(7) 0.2147(2) 0.68834(11) 0.0258(7) Uani 1 1 d . . . . .
H1A H 0.489534 0.201059 0.671884 0.031 Uiso 1 1 calc R . . . .
C19 C 0.7282(7) 1.0156(2) 0.60807(12) 0.0286(8) Uani 1 1 d . . . . .
H19 H 0.757542 1.055196 0.579844 0.034 Uiso 1 1 calc R . . . .
C10 C 0.4482(6) 0.7035(2) 0.64229(12) 0.0247(7) Uani 1 1 d . . . . .
H10A H 0.573466 0.699916 0.616796 0.030 Uiso 1 1 calc R . . . .
H10B H 0.526911 0.696470 0.674439 0.030 Uiso 1 1 calc R . . . .
C8 C 0.1890(6) 0.3111(2) 0.57820(11) 0.0227(7) Uani 1 1 d . . . . .
C21 C 0.8197(8) 0.9721(2) 0.69113(13) 0.0337(9) Uani 1 1 d . . . . .
H21 H 0.912885 0.983004 0.719618 0.040 Uiso 1 1 calc R . . . .
C4 C -0.0809(7) 0.2527(3) 0.73627(12) 0.0350(9) Uani 1 1 d . . . . .
H4 H -0.228087 0.265410 0.752562 0.042 Uiso 1 1 calc R . . . .
C3 C 0.0684(7) 0.1779(3) 0.75305(12) 0.0367(10) Uani 1 1 d . . . . .
H3 H 0.025981 0.140071 0.781132 0.044 Uiso 1 1 calc R . . . .
C20 C 0.8621(7) 1.0297(2) 0.64994(13) 0.0334(9) Uani 1 1 d . . . . .
H20 H 0.984492 1.079427 0.650451 0.040 Uiso 1 1 calc R . . . .
C2 C 0.2805(7) 0.1582(2) 0.72886(12) 0.0334(9) Uani 1 1 d . . . . .
H2 H 0.383200 0.105969 0.739993 0.040 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
Cl2 C8 1.769(3) . ?
Cl3 C8 1.766(3) . ?
Cl1 C8 1.774(3) . ?
O2 C9 1.353(4) . ?
O2 C10 1.447(4) . ?
O1 C9 1.205(4) . ?
N1 C9 1.351(4) . ?
N1 C7 1.450(4) . ?
C6 C7 1.520(4) . ?
C6 C5 1.385(5) . ?
C6 C1 1.390(4) . ?
C18 C17 1.474(5) . ?
C18 C23 1.401(4) . ?
C18 C19 1.385(5) . ?
C13 C12 1.376(4) . ?
C13 C14 1.393(5) . ?
C17 C12 1.396(4) . ?
C17 C16 1.386(4) . ?
C23 C22 1.381(4) . ?
C23 C11 1.518(4) . ?
C7 C8 1.550(4) . ?
C12 C11 1.516(4) . ?
C14 C15 1.382(5) . ?
C15 C16 1.378(5) . ?
C5 C4 1.389(5) . ?
C22 C21 1.383(5) . ?
C11 C10 1.523(4) . ?
C1 C2 1.386(4) . ?
C19 C20 1.383(5) . ?
C21 C20 1.385(5) . ?
C4 C3 1.375(5) . ?
C3 C2 1.382(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
C9 O2 C10 113.6(3) . . ?
C9 N1 C7 120.1(3) . . ?
O1 C9 O2 124.2(3) . . ?
O1 C9 N1 125.7(3) . . ?
N1 C9 O2 110.1(3) . . ?
C5 C6 C7 122.1(3) . . ?
C5 C6 C1 119.1(3) . . ?
C1 C6 C7 118.7(3) . . ?
C23 C18 C17 107.9(3) . . ?
C19 C18 C17 131.6(3) . . ?
C19 C18 C23 120.5(3) . . ?
C12 C13 C14 118.6(3) . . ?
C12 C17 C18 108.9(3) . . ?
C16 C17 C18 130.3(3) . . ?
C16 C17 C12 120.8(3) . . ?
C18 C23 C11 110.5(3) . . ?
C22 C23 C18 120.4(3) . . ?
C22 C23 C11 128.9(3) . . ?
N1 C7 C6 113.3(3) . . ?
N1 C7 C8 109.0(3) . . ?
C6 C7 C8 114.1(2) . . ?
C13 C12 C17 120.5(3) . . ?
C13 C12 C11 129.2(3) . . ?
C17 C12 C11 110.3(3) . . ?
C15 C14 C13 120.6(3) . . ?
C16 C15 C14 121.1(3) . . ?
C6 C5 C4 119.9(3) . . ?
C15 C16 C17 118.4(3) . . ?
C23 C22 C21 118.9(3) . . ?
C23 C11 C10 106.2(3) . . ?
C12 C11 C23 102.0(2) . . ?
C12 C11 C10 113.7(2) . . ?
C2 C1 C6 120.6(4) . . ?
C20 C19 C18 118.7(3) . . ?
O2 C10 C11 109.8(3) . . ?
Cl2 C8 Cl1 108.01(16) . . ?
Cl3 C8 Cl2 108.88(18) . . ?
Cl3 C8 Cl1 108.40(17) . . ?
C7 C8 Cl2 110.7(2) . . ?
C7 C8 Cl3 111.7(2) . . ?
C7 C8 Cl1 109.1(2) . . ?
C22 C21 C20 120.8(3) . . ?
C3 C4 C5 120.7(4) . . ?
C4 C3 C2 119.6(3) . . ?
C19 C20 C21 120.8(4) . . ?
C3 C2 C1 120.0(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
