# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_ljy-20220115
_database_code_depnum_ccdc_archive 'CCDC 2142480'
loop_
_audit_author_name
_audit_author_address
'Zhiguo Zhang'
;Henan Normal University
China
;
_audit_update_record             
;
2022-01-17 deposited with the CCDC.	2023-09-06 downloaded from the CCDC.
;
_audit_creation_date             2022-01-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 Cl N O'
_chemical_formula_sum            'C19 H17 Cl N O'
_chemical_formula_weight         310.79
_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 0.0181 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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0254(3)
_cell_length_b                   8.4668(4)
_cell_length_c                   13.4722(6)
_cell_angle_alpha                82.729(4)
_cell_angle_beta                 86.836(4)
_cell_angle_gamma                75.912(4)
_cell_volume                     770.76(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12540
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.187
_cell_measurement_theta_min      3.554
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    2.189
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             326
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5569
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.540
_diffrn_reflns_theta_min         5.424
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  template
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2732
_reflns_number_total             2917
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2917
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.034
_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)+(0.0572P)²+0.2986P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1066
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C8(H8), C11(H11), C9(H9), C15(H15), C16(H16), C19(H19), C18(H18)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl20 Cl 0.33132(8) 0.20245(6) 1.06446(3) 0.05122(18) Uani 1 1 d . . . . .
O21 O 0.04399(15) 0.66834(13) 0.62326(8) 0.0274(3) Uani 1 1 d . . . . .
N1 N 0.30157(18) 0.73976(15) 0.52866(9) 0.0216(3) Uani 1 1 d . . . . .
C14 C 0.3382(2) 0.57236(18) 0.79273(11) 0.0226(3) Uani 1 1 d . . . . .
C12 C 0.1386(2) 0.65907(17) 0.39362(11) 0.0222(3) Uani 1 1 d . . . . .
H12 H 0.137718 0.559360 0.431363 0.027 Uiso 1 1 calc R U . . .
C7 C 0.2141(2) 0.77412(17) 0.43244(10) 0.0202(3) Uani 1 1 d . . . . .
C2 C 0.4989(2) 0.74519(17) 0.54256(11) 0.0217(3) Uani 1 1 d . . . . .
C6 C 0.2064(2) 0.69559(17) 0.61663(11) 0.0208(3) Uani 1 1 d . . . . .
C5 C 0.3393(2) 0.69214(18) 0.70175(11) 0.0220(3) Uani 1 1 d . . . . .
C3 C 0.5240(2) 0.73200(18) 0.65191(11) 0.0233(3) Uani 1 1 d . . . . .
H3 H 0.652348 0.678834 0.680509 0.028 Uiso 1 1 calc R U . . .
C8 C 0.2106(2) 0.92478(18) 0.37683(12) 0.0249(3) Uani 1 1 d . . . . .
H8 H 0.256735 1.003734 0.403881 0.030 Uiso 1 1 calc R U . . .
C10 C 0.0665(2) 0.84096(19) 0.23943(11) 0.0246(3) Uani 1 1 d . . . . .
C4 C 0.3815(2) 0.85854(19) 0.70587(12) 0.0270(3) Uani 1 1 d . . . . .
H4A H 0.302217 0.952058 0.665633 0.032 Uiso 1 1 calc R U . . .
H4B H 0.420446 0.881942 0.769353 0.032 Uiso 1 1 calc R U . . .
C11 C 0.0642(2) 0.69380(19) 0.29770(12) 0.0254(3) Uani 1 1 d . . . . .
H11 H 0.011776 0.617003 0.272056 0.030 Uiso 1 1 calc R U . . .
C22 C 0.6340(2) 0.7557(2) 0.47109(12) 0.0272(3) Uani 1 1 d . . . . .
C9 C 0.1382(2) 0.95659(18) 0.28111(12) 0.0264(3) Uani 1 1 d . . . . .
H9 H 0.137311 1.057063 0.243906 0.032 Uiso 1 1 calc R U . . .
C15 C 0.4359(2) 0.4091(2) 0.79079(12) 0.0298(4) Uani 1 1 d . . . . .
H15 H 0.502328 0.375692 0.732540 0.036 Uiso 1 1 calc R U . . .
C17 C 0.3385(3) 0.3457(2) 0.95999(12) 0.0314(4) Uani 1 1 d . . . . .
C16 C 0.4360(3) 0.2951(2) 0.87413(14) 0.0351(4) Uani 1 1 d . . . . .
H16 H 0.501197 0.185846 0.871995 0.042 Uiso 1 1 calc R U . . .
C19 C 0.2421(3) 0.6194(2) 0.88060(14) 0.0393(4) Uani 1 1 d . . . . .
H19 H 0.176321 0.728356 0.883189 0.047 Uiso 1 1 calc R U . . .
C13 C -0.0056(3) 0.8758(2) 0.13346(13) 0.0368(4) Uani 1 1 d . . . . .
H13A H -0.006503 0.774501 0.108736 0.055 Uiso 1 1 calc R U . . .
H13B H 0.080070 0.930154 0.091774 0.055 Uiso 1 1 calc R U . . .
H13C H -0.136152 0.944840 0.132523 0.055 Uiso 1 1 calc R U . . .
C18 C 0.2421(3) 0.5067(2) 0.96491(13) 0.0432(5) Uani 1 1 d . . . . .
H18 H 0.177871 0.539511 1.023776 0.052 Uiso 1 1 calc R U . . .
H22A H 0.762(3) 0.758(2) 0.4897(14) 0.030(5) Uiso 1 1 d . . . . .
H22B H 0.608(3) 0.764(2) 0.4009(16) 0.034(5) Uiso 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
Cl20 C17 1.7449(16) . ?
O21 C6 1.2144(18) . ?
N1 C7 1.4311(18) . ?
N1 C2 1.4213(18) . ?
N1 C6 1.3834(19) . ?
C14 C5 1.490(2) . ?
C14 C15 1.389(2) . ?
C14 C19 1.384(2) . ?
C12 H12 0.9300 . ?
C12 C7 1.384(2) . ?
C12 C11 1.391(2) . ?
C7 C8 1.391(2) . ?
C2 C3 1.480(2) . ?
C2 C22 1.325(2) . ?
C6 C5 1.5111(19) . ?
C5 C3 1.520(2) . ?
C5 C4 1.517(2) . ?
C3 H3 0.9800 . ?
C3 C4 1.508(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.383(2) . ?
C10 C11 1.389(2) . ?
C10 C9 1.392(2) . ?
C10 C13 1.511(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C11 H11 0.9300 . ?
C22 H22A 0.952(19) . ?
C22 H22B 0.96(2) . ?
C9 H9 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.385(2) . ?
C17 C16 1.374(3) . ?
C17 C18 1.374(3) . ?
C16 H16 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.388(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C18 H18 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
C2 N1 C7 122.61(12) . . ?
C6 N1 C7 124.20(12) . . ?
C6 N1 C2 113.17(12) . . ?
C15 C14 C5 119.97(14) . . ?
C19 C14 C5 121.65(14) . . ?
C19 C14 C15 118.38(14) . . ?
C7 C12 H12 120.3 . . ?
C7 C12 C11 119.44(13) . . ?
C11 C12 H12 120.3 . . ?
C12 C7 N1 121.17(13) . . ?
C12 C7 C8 120.14(13) . . ?
C8 C7 N1 118.67(12) . . ?
N1 C2 C3 106.60(12) . . ?
C22 C2 N1 126.25(14) . . ?
C22 C2 C3 127.14(14) . . ?
O21 C6 N1 125.67(13) . . ?
O21 C6 C5 126.89(13) . . ?
N1 C6 C5 107.42(12) . . ?
C14 C5 C6 119.52(12) . . ?
C14 C5 C3 124.09(12) . . ?
C14 C5 C4 122.29(13) . . ?
C6 C5 C3 105.11(12) . . ?
C6 C5 C4 111.59(12) . . ?
C4 C5 C3 59.54(10) . . ?
C2 C3 C5 106.69(12) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 115.54(13) . . ?
C5 C3 H3 119.8 . . ?
C4 C3 C5 60.13(10) . . ?
C4 C3 H3 119.8 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.65(13) . . ?
C9 C8 H8 120.2 . . ?
C11 C10 C9 118.20(14) . . ?
C11 C10 C13 121.41(14) . . ?
C9 C10 C13 120.39(14) . . ?
C5 C4 H4A 117.7 . . ?
C5 C4 H4B 117.7 . . ?
C3 C4 C5 60.32(10) . . ?
C3 C4 H4A 117.7 . . ?
C3 C4 H4B 117.7 . . ?
H4A C4 H4B 114.9 . . ?
C12 C11 H11 119.4 . . ?
C10 C11 C12 121.29(14) . . ?
C10 C11 H11 119.4 . . ?
C2 C22 H22A 118.6(11) . . ?
C2 C22 H22B 122.9(12) . . ?
H22A C22 H22B 118.4(16) . . ?
C8 C9 C10 121.20(14) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.10(15) . . ?
C16 C15 H15 119.4 . . ?
C16 C17 Cl20 119.54(14) . . ?
C16 C17 C18 121.44(15) . . ?
C18 C17 Cl20 119.00(13) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.02(16) . . ?
C17 C16 H16 120.5 . . ?
C14 C19 H19 119.4 . . ?
C14 C19 C18 121.14(16) . . ?
C18 C19 H19 119.4 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C17 C18 C19 118.92(16) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?

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
Cl20 C17 C16 C15 178.16(13) . . . . ?
Cl20 C17 C18 C19 -177.74(15) . . . . ?
O21 C6 C5 C14 34.0(2) . . . . ?
O21 C6 C5 C3 179.05(14) . . . . ?
O21 C6 C5 C4 -118.20(16) . . . . ?
N1 C7 C8 C9 175.90(14) . . . . ?
N1 C2 C3 C5 8.55(15) . . . . ?
N1 C2 C3 C4 -55.80(16) . . . . ?
N1 C6 C5 C14 -147.49(13) . . . . ?
N1 C6 C5 C3 -2.40(15) . . . . ?
N1 C6 C5 C4 60.36(15) . . . . ?
C14 C5 C3 C2 139.20(14) . . . . ?
C14 C5 C3 C4 -110.50(16) . . . . ?
C14 C5 C4 C3 113.43(15) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C14 C19 C18 C17 -0.5(3) . . . . ?
C12 C7 C8 C9 -2.4(2) . . . . ?
C7 N1 C2 C3 170.26(12) . . . . ?
C7 N1 C2 C22 -11.3(2) . . . . ?
C7 N1 C6 O21 5.8(2) . . . . ?
C7 N1 C6 C5 -172.76(12) . . . . ?
C7 C12 C11 C10 0.9(2) . . . . ?
C7 C8 C9 C10 0.7(2) . . . . ?
C2 N1 C7 C12 121.24(15) . . . . ?
C2 N1 C7 C8 -57.08(19) . . . . ?
C2 N1 C6 O21 -173.12(14) . . . . ?
C2 N1 C6 C5 8.30(16) . . . . ?
C2 C3 C4 C5 95.32(13) . . . . ?
C6 N1 C7 C12 -57.6(2) . . . . ?
C6 N1 C7 C8 124.08(16) . . . . ?
C6 N1 C2 C3 -10.79(16) . . . . ?
C6 N1 C2 C22 167.63(15) . . . . ?
C6 C5 C3 C2 -3.84(15) . . . . ?
C6 C5 C3 C4 106.46(13) . . . . ?
C6 C5 C4 C3 -95.31(13) . . . . ?
C5 C14 C15 C16 -179.55(15) . . . . ?
C5 C14 C19 C18 179.98(17) . . . . ?
C4 C5 C3 C2 -110.29(13) . . . . ?
C11 C12 C7 N1 -176.63(13) . . . . ?
C11 C12 C7 C8 1.7(2) . . . . ?
C11 C10 C9 C8 1.8(2) . . . . ?
C22 C2 C3 C5 -169.85(15) . . . . ?
C22 C2 C3 C4 125.81(17) . . . . ?
C9 C10 C11 C12 -2.6(2) . . . . ?
C15 C14 C5 C6 77.47(19) . . . . ?
C15 C14 C5 C3 -60.7(2) . . . . ?
C15 C14 C5 C4 -133.45(16) . . . . ?
C15 C14 C19 C18 -0.2(3) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C19 C14 C5 C6 -102.72(18) . . . . ?
C19 C14 C5 C3 119.12(18) . . . . ?
C19 C14 C5 C4 46.4(2) . . . . ?
C19 C14 C15 C16 0.6(3) . . . . ?
C13 C10 C11 C12 177.10(15) . . . . ?
C13 C10 C9 C8 -177.89(15) . . . . ?
C18 C17 C16 C15 -0.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
