# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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 2049393'
loop_
_audit_author_name
_audit_author_address
'chen rongxiang'
;xinxiang university
China
;
_audit_update_record             
;
2020-12-10 deposited with the CCDC.	2021-02-12 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            'C22 H14 Cl N O4'
_chemical_formula_weight         391.79

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'

_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                   20.415(3)
_cell_length_b                   5.9806(8)
_cell_length_c                   15.390(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.234(2)
_cell_angle_gamma                90
_cell_volume                     1813.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3517
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      27.48

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.240
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9452
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.743
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3540
_reflns_number_gt                2580
_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    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0483P)²+0.4600P] 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         3540
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.0906
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.58145(3) 0.75009(11) 0.96095(4) 0.0726(2) Uani 1 1 d . . . . .
O3 O 0.21891(6) 0.2508(2) 0.71508(8) 0.0402(3) Uani 1 1 d . . . . .
O4 O 0.33966(7) 0.0720(2) 0.72961(9) 0.0530(4) Uani 1 1 d . . . . .
O2 O 0.11239(7) 0.0300(2) 0.59218(10) 0.0568(4) Uani 1 1 d . . . . .
O1 O 0.16384(7) 0.6405(3) 0.77490(9) 0.0584(4) Uani 1 1 d . . . . .
N1 N 0.15486(7) 0.3393(3) 0.67878(10) 0.0387(4) Uani 1 1 d . . . . .
C10 C 0.26472(8) 0.4335(3) 0.59925(11) 0.0305(4) Uani 1 1 d . . . . .
C17 C 0.39639(8) 0.3988(3) 0.79398(11) 0.0319(4) Uani 1 1 d . . . . .
C9 C 0.27061(8) 0.3965(3) 0.69768(11) 0.0328(4) Uani 1 1 d . . . . .
H9 H 0.2700 0.5404 0.7279 0.039 Uiso 1 1 calc R U . . .
C16 C 0.33678(8) 0.2714(3) 0.74098(11) 0.0334(4) Uani 1 1 d . . . . .
C11 C 0.24513(8) 0.2626(3) 0.53682(11) 0.0353(4) Uani 1 1 d . . . . .
H11 H 0.2335 0.1232 0.5551 0.042 Uiso 1 1 calc R U . . .
C5 C 0.04080(8) 0.3363(3) 0.61828(12) 0.0369(4) Uani 1 1 d . . . . .
C8 C 0.13032(9) 0.5226(3) 0.71678(12) 0.0391(4) Uani 1 1 d . . . . .
C6 C 0.05654(9) 0.5263(3) 0.67069(12) 0.0378(4) Uani 1 1 d . . . . .
C18 C 0.46012(9) 0.2972(3) 0.81230(12) 0.0409(4) Uani 1 1 d . . . . .
H18 H 0.4643 0.1556 0.7894 0.049 Uiso 1 1 calc R U . . .
C12 C 0.24287(9) 0.3000(3) 0.44729(12) 0.0418(5) Uani 1 1 d . . . . .
H12 H 0.2293 0.1860 0.4054 0.050 Uiso 1 1 calc R U . . .
C7 C 0.10388(9) 0.2072(3) 0.62428(12) 0.0390(4) Uani 1 1 d . . . . .
C22 C 0.39125(9) 0.6087(3) 0.82938(12) 0.0415(4) Uani 1 1 d . . . . .
H22 H 0.3492 0.6789 0.8175 0.050 Uiso 1 1 calc R U . . .
C15 C 0.28242(10) 0.6394(3) 0.57143(13) 0.0425(4) Uani 1 1 d . . . . .
H15 H 0.2954 0.7548 0.6129 0.051 Uiso 1 1 calc R U . . .
C20 C 0.50985(9) 0.6126(4) 0.89793(12) 0.0456(5) Uani 1 1 d . . . . .
C19 C 0.51673(9) 0.4036(4) 0.86366(13) 0.0480(5) Uani 1 1 d . . . . .
H19 H 0.5591 0.3356 0.8752 0.058 Uiso 1 1 calc R U . . .
C21 C 0.44799(10) 0.7156(3) 0.88233(14) 0.0481(5) Uani 1 1 d . . . . .
H21 H 0.4441 0.8554 0.9069 0.058 Uiso 1 1 calc R U . . .
C13 C 0.26065(10) 0.5053(3) 0.42014(13) 0.0493(5) Uani 1 1 d . . . . .
H13 H 0.2590 0.5297 0.3599 0.059 Uiso 1 1 calc R U . . .
C4 C -0.02528(9) 0.2907(3) 0.57050(13) 0.0471(5) Uani 1 1 d . . . . .
H4 H -0.0361 0.1622 0.5357 0.057 Uiso 1 1 calc R U . . .
C14 C 0.28088(11) 0.6745(3) 0.48185(14) 0.0534(5) Uani 1 1 d . . . . .
H14 H 0.2935 0.8124 0.4635 0.064 Uiso 1 1 calc R U . . .
C1 C 0.00776(10) 0.6809(4) 0.67583(14) 0.0495(5) Uani 1 1 d . . . . .
H1 H 0.0188 0.8101 0.7102 0.059 Uiso 1 1 calc R U . . .
C3 C -0.07469(10) 0.4446(4) 0.57667(14) 0.0546(5) Uani 1 1 d . . . . .
H3 H -0.1197 0.4181 0.5457 0.066 Uiso 1 1 calc R U . . .
C2 C -0.05853(10) 0.6361(4) 0.62770(15) 0.0557(6) Uani 1 1 d . . . . .
H2 H -0.0927 0.7371 0.6299 0.067 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 C20 1.7343(18) . ?
O3 N1 1.3849(18) . ?
O3 C9 1.447(2) . ?
O4 C16 1.209(2) . ?
O2 C7 1.201(2) . ?
O1 C8 1.202(2) . ?
N1 C8 1.396(2) . ?
N1 C7 1.397(2) . ?
C10 C15 1.383(2) . ?
C10 C11 1.388(2) . ?
C10 C9 1.504(2) . ?
C17 C22 1.383(3) . ?
C17 C18 1.396(2) . ?
C17 C16 1.485(2) . ?
C9 C16 1.534(2) . ?
C9 H9 0.9800 . ?
C11 C12 1.385(3) . ?
C11 H11 0.9300 . ?
C5 C6 1.382(2) . ?
C5 C4 1.383(2) . ?
C5 C7 1.483(3) . ?
C8 C6 1.487(2) . ?
C6 C1 1.376(3) . ?
C18 C19 1.373(3) . ?
C18 H18 0.9300 . ?
C12 C13 1.376(3) . ?
C12 H12 0.9300 . ?
C22 C21 1.385(3) . ?
C22 H22 0.9300 . ?
C15 C14 1.387(3) . ?
C15 H15 0.9300 . ?
C20 C21 1.368(3) . ?
C20 C19 1.378(3) . ?
C19 H19 0.9300 . ?
C21 H21 0.9300 . ?
C13 C14 1.375(3) . ?
C13 H13 0.9300 . ?
C4 C3 1.387(3) . ?
C4 H4 0.9300 . ?
C14 H14 0.9300 . ?
C1 C2 1.387(3) . ?
C1 H1 0.9300 . ?
C3 C2 1.379(3) . ?
C3 H3 0.9300 . ?
C2 H2 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
N1 O3 C9 110.65(12) . . ?
O3 N1 C8 122.39(13) . . ?
O3 N1 C7 120.11(14) . . ?
C8 N1 C7 113.75(14) . . ?
C15 C10 C11 119.52(16) . . ?
C15 C10 C9 118.99(15) . . ?
C11 C10 C9 121.41(15) . . ?
C22 C17 C18 118.58(16) . . ?
C22 C17 C16 123.08(15) . . ?
C18 C17 C16 118.27(16) . . ?
O3 C9 C10 113.94(13) . . ?
O3 C9 C16 103.17(13) . . ?
C10 C9 C16 109.72(13) . . ?
O3 C9 H9 109.9 . . ?
C10 C9 H9 109.9 . . ?
C16 C9 H9 109.9 . . ?
O4 C16 C17 121.43(15) . . ?
O4 C16 C9 119.25(15) . . ?
C17 C16 C9 119.31(14) . . ?
C12 C11 C10 119.89(17) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C6 C5 C4 121.13(18) . . ?
C6 C5 C7 109.09(15) . . ?
C4 C5 C7 129.78(18) . . ?
O1 C8 N1 125.16(16) . . ?
O1 C8 C6 130.82(17) . . ?
N1 C8 C6 104.00(14) . . ?
C1 C6 C5 121.69(17) . . ?
C1 C6 C8 129.81(17) . . ?
C5 C6 C8 108.49(15) . . ?
C19 C18 C17 120.90(18) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C13 C12 C11 120.26(17) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
O2 C7 N1 125.47(17) . . ?
O2 C7 C5 130.61(17) . . ?
N1 C7 C5 103.92(15) . . ?
C17 C22 C21 120.81(17) . . ?
C17 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C10 C15 C14 120.19(18) . . ?
C10 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C21 C20 C19 121.54(17) . . ?
C21 C20 Cl1 119.22(16) . . ?
C19 C20 Cl1 119.23(15) . . ?
C18 C19 C20 119.06(17) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C20 C21 C22 119.10(19) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C14 C13 C12 120.14(18) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C5 C4 C3 117.27(19) . . ?
C5 C4 H4 121.4 . . ?
C3 C4 H4 121.4 . . ?
C13 C14 C15 119.99(19) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C6 C1 C2 117.29(19) . . ?
C6 C1 H1 121.4 . . ?
C2 C1 H1 121.4 . . ?
C2 C3 C4 121.37(18) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?

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
C9 O3 N1 C8 -73.47(19) . . . . ?
C9 O3 N1 C7 129.70(16) . . . . ?
N1 O3 C9 C10 -60.37(17) . . . . ?
N1 O3 C9 C16 -179.26(12) . . . . ?
C15 C10 C9 O3 145.60(15) . . . . ?
C11 C10 C9 O3 -37.5(2) . . . . ?
C15 C10 C9 C16 -99.31(18) . . . . ?
C11 C10 C9 C16 77.54(18) . . . . ?
C22 C17 C16 O4 -161.77(18) . . . . ?
C18 C17 C16 O4 15.2(3) . . . . ?
C22 C17 C16 C9 19.8(2) . . . . ?
C18 C17 C16 C9 -163.22(15) . . . . ?
O3 C9 C16 O4 43.8(2) . . . . ?
C10 C9 C16 O4 -78.0(2) . . . . ?
O3 C9 C16 C17 -137.71(15) . . . . ?
C10 C9 C16 C17 100.51(17) . . . . ?
C15 C10 C11 C12 -0.6(2) . . . . ?
C9 C10 C11 C12 -177.40(14) . . . . ?
O3 N1 C8 O1 11.2(3) . . . . ?
C7 N1 C8 O1 169.34(18) . . . . ?
O3 N1 C8 C6 -167.31(14) . . . . ?
C7 N1 C8 C6 -9.1(2) . . . . ?
C4 C5 C6 C1 -1.7(3) . . . . ?
C7 C5 C6 C1 178.24(17) . . . . ?
C4 C5 C6 C8 177.20(17) . . . . ?
C7 C5 C6 C8 -2.8(2) . . . . ?
O1 C8 C6 C1 7.5(3) . . . . ?
N1 C8 C6 C1 -174.13(19) . . . . ?
O1 C8 C6 C5 -171.3(2) . . . . ?
N1 C8 C6 C5 7.06(19) . . . . ?
C22 C17 C18 C19 -0.6(3) . . . . ?
C16 C17 C18 C19 -177.69(16) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
O3 N1 C7 O2 -13.3(3) . . . . ?
C8 N1 C7 O2 -172.02(19) . . . . ?
O3 N1 C7 C5 166.21(14) . . . . ?
C8 N1 C7 C5 7.5(2) . . . . ?
C6 C5 C7 O2 177.0(2) . . . . ?
C4 C5 C7 O2 -3.1(4) . . . . ?
C6 C5 C7 N1 -2.51(19) . . . . ?
C4 C5 C7 N1 177.45(19) . . . . ?
C18 C17 C22 C21 -0.4(3) . . . . ?
C16 C17 C22 C21 176.60(17) . . . . ?
C11 C10 C15 C14 -0.3(3) . . . . ?
C9 C10 C15 C14 176.61(16) . . . . ?
C17 C18 C19 C20 0.6(3) . . . . ?
C21 C20 C19 C18 0.4(3) . . . . ?
Cl1 C20 C19 C18 -178.70(15) . . . . ?
C19 C20 C21 C22 -1.3(3) . . . . ?
Cl1 C20 C21 C22 177.78(15) . . . . ?
C17 C22 C21 C20 1.3(3) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C6 C5 C4 C3 0.7(3) . . . . ?
C7 C5 C4 C3 -179.25(18) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C10 C15 C14 C13 1.1(3) . . . . ?
C5 C6 C1 C2 1.4(3) . . . . ?
C8 C6 C1 C2 -177.25(19) . . . . ?
C5 C4 C3 C2 0.5(3) . . . . ?
C4 C3 C2 C1 -0.8(3) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?

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
C9 H9 O1 0.98 2.53 3.107(2) 117.5 .

_refine_diff_density_max         0.148
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.043

