# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 2181906'
loop_
_audit_author_name
_audit_author_address
'Sheng-Jiao Yan'
;Yunnan University
China
;
_audit_update_record             
;
2022-06-26 deposited with the CCDC.	2022-08-15 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            'C18 H12 Cl N O3'
_chemical_formula_weight         325.74

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.6982(9)
_cell_length_b                   12.4059(8)
_cell_length_c                   7.6199(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.261(2)
_cell_angle_gamma                90
_cell_volume                     1460.24(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    8749
_cell_measurement_theta_min      2.6371
_cell_measurement_theta_max      27.9379

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.277
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      301(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  graphite
_diffrn_measurement_method       'CCD area detector'
_diffrn_detector_area_resol_mean 'phi and omega scans'
_diffrn_reflns_number            33858
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_av_R_equivalents  0.0984
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.105
_diffrn_reflns_theta_max         25.139
_diffrn_reflns_theta_full        25.139
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2607
_reflns_number_gt                2004
_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'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0697P)²+0.5156P] 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         2607
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1412
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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
Cl1 Cl 0.35319(4) 0.17398(6) 0.74260(10) 0.0639(3) Uani 1 1 d . . . . .
N1 N 0.81444(12) 0.33540(15) 0.5391(3) 0.0459(5) Uani 1 1 d . . . . .
O1 O 0.67564(10) 0.36401(12) 0.6028(2) 0.0459(4) Uani 1 1 d . . . . .
O2 O 0.65214(12) 0.03021(13) 0.5895(3) 0.0614(5) Uani 1 1 d . . . . .
O3 O 0.92557(12) 0.76020(15) 0.6404(3) 0.0653(5) Uani 1 1 d . . . . .
C1 C 0.44903(15) 0.2280(2) 0.6976(3) 0.0472(6) Uani 1 1 d . . . . .
C2 C 0.46051(16) 0.3393(2) 0.7039(3) 0.0498(6) Uani 1 1 d . . . . .
H2 H 0.417251 0.384153 0.731158 0.060 Uiso 1 1 calc R U . . .
C3 C 0.53651(15) 0.3819(2) 0.6693(3) 0.0481(6) Uani 1 1 d . . . . .
H3 H 0.544740 0.456126 0.670652 0.058 Uiso 1 1 calc R U . . .
C4 C 0.60088(14) 0.31355(17) 0.6323(3) 0.0407(5) Uani 1 1 d . . . . .
C5 C 0.59064(14) 0.20235(18) 0.6259(3) 0.0414(5) Uani 1 1 d . . . . .
C6 C 0.51193(15) 0.16061(19) 0.6582(3) 0.0448(5) Uani 1 1 d . . . . .
H6 H 0.502418 0.086597 0.652806 0.054 Uiso 1 1 calc R U . . .
C7 C 0.65999(15) 0.12913(19) 0.5885(3) 0.0450(5) Uani 1 1 d . . . . .
C8 C 0.73501(15) 0.18612(18) 0.5563(3) 0.0440(5) Uani 1 1 d . . . . .
C9 C 0.73733(14) 0.29648(19) 0.5671(3) 0.0422(5) Uani 1 1 d . . . . .
C10 C 0.81734(17) 0.1555(2) 0.5166(4) 0.0549(6) Uani 1 1 d . . . . .
H10 H 0.835568 0.085571 0.499493 0.066 Uiso 1 1 calc R U . . .
C11 C 0.86361(17) 0.2458(2) 0.5083(4) 0.0557(7) Uani 1 1 d . . . . .
H11 H 0.919839 0.248308 0.485507 0.067 Uiso 1 1 calc R U . . .
C12 C 0.84257(14) 0.44512(19) 0.5575(3) 0.0447(5) Uani 1 1 d . . . . .
C13 C 0.78876(16) 0.5268(2) 0.4839(3) 0.0532(6) Uani 1 1 d . . . . .
H13 H 0.734807 0.510596 0.416755 0.064 Uiso 1 1 calc R U . . .
C14 C 0.81482(16) 0.6336(2) 0.5097(3) 0.0518(6) Uani 1 1 d . . . . .
H14 H 0.777917 0.688877 0.461461 0.062 Uiso 1 1 calc R U . . .
C15 C 0.89515(15) 0.6575(2) 0.6064(3) 0.0485(6) Uani 1 1 d . . . . .
C16 C 0.94992(16) 0.5747(2) 0.6765(4) 0.0578(7) Uani 1 1 d . . . . .
H16 H 1.004917 0.590551 0.739130 0.069 Uiso 1 1 calc R U . . .
C17 C 0.92345(15) 0.4694(2) 0.6539(4) 0.0531(6) Uani 1 1 d . . . . .
H17 H 0.960053 0.414233 0.703612 0.064 Uiso 1 1 calc R U . . .
C18 C 0.8680(2) 0.8462(2) 0.5790(4) 0.0696(8) Uani 1 1 d . . . . .
H18A H 0.853886 0.844228 0.451181 0.104 Uiso 1 1 calc R U . . .
H18B H 0.895228 0.913672 0.616419 0.104 Uiso 1 1 calc R U . . .
H18C H 0.816050 0.838664 0.627983 0.104 Uiso 1 1 calc R U . . .


_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 C1 1.736(2) . ?
N1 C9 1.355(3) . ?
N1 C11 1.397(3) . ?
N1 C12 1.430(3) . ?
O1 C9 1.345(3) . ?
O1 C4 1.383(3) . ?
O2 C7 1.234(3) . ?
O3 C15 1.369(3) . ?
O3 C18 1.422(3) . ?
C1 C6 1.367(3) . ?
C1 C2 1.392(3) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(3) . ?
C5 C6 1.401(3) . ?
C5 C7 1.484(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.432(3) . ?
C8 C9 1.372(3) . ?
C8 C10 1.430(3) . ?
C10 C11 1.343(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.373(3) . ?
C12 C17 1.382(3) . ?
C13 C14 1.391(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(4) . ?
C16 C17 1.373(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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 N1 C11 106.2(2) . . ?
C9 N1 C12 126.35(19) . . ?
C11 N1 C12 127.1(2) . . ?
C9 O1 C4 114.42(17) . . ?
C15 O3 C18 117.1(2) . . ?
C6 C1 C2 121.3(2) . . ?
C6 C1 Cl1 119.5(2) . . ?
C2 C1 Cl1 119.16(19) . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
O1 C4 C3 115.3(2) . . ?
O1 C4 C5 122.7(2) . . ?
C3 C4 C5 122.0(2) . . ?
C4 C5 C6 117.5(2) . . ?
C4 C5 C7 122.0(2) . . ?
C6 C5 C7 120.5(2) . . ?
C1 C6 C5 120.4(2) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O2 C7 C8 125.3(2) . . ?
O2 C7 C5 122.0(2) . . ?
C8 C7 C5 112.6(2) . . ?
C9 C8 C10 105.2(2) . . ?
C9 C8 C7 119.8(2) . . ?
C10 C8 C7 135.0(2) . . ?
O1 C9 N1 120.4(2) . . ?
O1 C9 C8 128.4(2) . . ?
N1 C9 C8 111.2(2) . . ?
C11 C10 C8 107.8(2) . . ?
C11 C10 H10 126.1 . . ?
C8 C10 H10 126.1 . . ?
C10 C11 N1 109.6(2) . . ?
C10 C11 H11 125.2 . . ?
N1 C11 H11 125.2 . . ?
C13 C12 C17 119.8(2) . . ?
C13 C12 N1 120.4(2) . . ?
C17 C12 N1 119.9(2) . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
O3 C15 C14 123.9(2) . . ?
O3 C15 C16 116.5(2) . . ?
C14 C15 C16 119.6(2) . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C12 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
C6 C1 C2 C3 0.2(4) . . . . ?
Cl1 C1 C2 C3 179.62(18) . . . . ?
C1 C2 C3 C4 -1.3(4) . . . . ?
C9 O1 C4 C3 -179.98(19) . . . . ?
C9 O1 C4 C5 0.1(3) . . . . ?
C2 C3 C4 O1 -178.8(2) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
O1 C4 C5 C6 179.97(19) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
O1 C4 C5 C7 0.6(3) . . . . ?
C3 C4 C5 C7 -179.2(2) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
Cl1 C1 C6 C5 -178.37(17) . . . . ?
C4 C5 C6 C1 -1.2(3) . . . . ?
C7 C5 C6 C1 178.2(2) . . . . ?
C4 C5 C7 O2 177.2(2) . . . . ?
C6 C5 C7 O2 -2.1(3) . . . . ?
C4 C5 C7 C8 -1.6(3) . . . . ?
C6 C5 C7 C8 179.1(2) . . . . ?
O2 C7 C8 C9 -176.9(2) . . . . ?
C5 C7 C8 C9 1.8(3) . . . . ?
O2 C7 C8 C10 0.8(4) . . . . ?
C5 C7 C8 C10 179.5(3) . . . . ?
C4 O1 C9 N1 -178.68(19) . . . . ?
C4 O1 C9 C8 0.2(3) . . . . ?
C11 N1 C9 O1 179.3(2) . . . . ?
C12 N1 C9 O1 5.5(3) . . . . ?
C11 N1 C9 C8 0.2(3) . . . . ?
C12 N1 C9 C8 -173.5(2) . . . . ?
C10 C8 C9 O1 -179.6(2) . . . . ?
C7 C8 C9 O1 -1.2(4) . . . . ?
C10 C8 C9 N1 -0.6(3) . . . . ?
C7 C8 C9 N1 177.7(2) . . . . ?
C9 C8 C10 C11 0.8(3) . . . . ?
C7 C8 C10 C11 -177.1(3) . . . . ?
C8 C10 C11 N1 -0.7(3) . . . . ?
C9 N1 C11 C10 0.3(3) . . . . ?
C12 N1 C11 C10 174.0(2) . . . . ?
C9 N1 C12 C13 -47.0(3) . . . . ?
C11 N1 C12 C13 140.6(3) . . . . ?
C9 N1 C12 C17 131.3(2) . . . . ?
C11 N1 C12 C17 -41.2(3) . . . . ?
C17 C12 C13 C14 -1.4(4) . . . . ?
N1 C12 C13 C14 176.8(2) . . . . ?
C12 C13 C14 C15 1.1(4) . . . . ?
C18 O3 C15 C14 3.4(4) . . . . ?
C18 O3 C15 C16 -176.1(2) . . . . ?
C13 C14 C15 O3 -179.0(2) . . . . ?
C13 C14 C15 C16 0.5(4) . . . . ?
O3 C15 C16 C17 177.8(2) . . . . ?
C14 C15 C16 C17 -1.8(4) . . . . ?
C15 C16 C17 C12 1.5(4) . . . . ?
C13 C12 C17 C16 0.1(4) . . . . ?
N1 C12 C17 C16 -178.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C14 H14 Cl1 0.93 2.90 3.814(3) 167.7 3_666 yes
C13 H13 O2 0.93 2.65 3.440(3) 143.6 4_565 yes
C2 H2 O2 0.93 2.62 3.494(3) 156.7 2_656 yes

_refine_diff_density_max         0.189
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.046



