# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_t_a
_database_code_depnum_ccdc_archive 'CCDC 2082705'
loop_
_audit_author_name
_audit_author_address
'Xinyue Chen'
;School of Chemistry and Chemical Engineering, Southeast University
China
;
_audit_update_record             
;
2021-05-10 deposited with the CCDC.	2021-07-27 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         'C17 H14 Cl N O4'
_chemical_formula_sum            'C17 H14 Cl N O4'
_chemical_formula_weight         331.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_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                   11.168(2)
_cell_length_b                   15.730(2)
_cell_length_c                   18.350(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.575(13)
_cell_angle_gamma                90
_cell_volume                     3105.2(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9948
_cell_measurement_theta_min      3.76
_cell_measurement_theta_max      68.24

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   0.6201
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    2.362
_shelx_estimated_absorpt_T_min   0.625
_shelx_estimated_absorpt_T_max   0.676
_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      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47550
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.761
_diffrn_reflns_theta_max         68.567
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5696
_reflns_number_gt                4444
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_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)+(0.0631P)²+1.2100P] 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         5696
_refine_ls_number_parameters     417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1303
_refine_ls_wR_factor_gt          0.1200
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.82508(9) 0.71610(4) 0.10852(3) 0.0835(3) Uani 1 1 d . . . . .
C1 C 0.88938(18) 0.65792(12) 0.46154(10) 0.0332(4) Uani 1 1 d . . . . .
H1 H 0.951245 0.673015 0.510206 0.040 Uiso 1 1 calc R U . . .
O1 O 0.81714(13) 0.43771(8) 0.44219(7) 0.0374(3) Uani 1 1 d . . . . .
N1 N 0.82181(15) 0.58085(10) 0.46956(8) 0.0336(4) Uani 1 1 d . . . . .
H1A H 0.763549 0.579983 0.493699 0.040 Uiso 1 1 calc R U . . .
Cl2 Cl 0.65697(10) 0.29540(4) 0.91177(4) 0.0895(3) Uani 1 1 d . . . . .
N2 N 0.65696(15) 0.41807(10) 0.54188(9) 0.0345(4) Uani 1 1 d . . . . .
H2 H 0.711084 0.420302 0.514821 0.041 Uiso 1 1 calc R U . . .
C2 C 0.80396(19) 0.73327(12) 0.43055(11) 0.0353(4) Uani 1 1 d . . . . .
H2A H 0.722811 0.726993 0.442152 0.042 Uiso 1 1 calc R U . . .
H2AB H 0.842553 0.787547 0.452169 0.042 Uiso 1 1 calc R U . . .
O2 O 1.06862(13) 0.51254(8) 0.31330(8) 0.0385(3) Uani 1 1 d . . . . .
C4 C 0.70370(19) 0.77258(12) 0.28914(12) 0.0418(5) Uani 1 1 d . . . . .
H4 H 0.640044 0.806003 0.300343 0.050 Uiso 1 1 calc R U . . .
O4 O 0.96500(15) 0.37638(11) 0.10038(10) 0.0603(5) Uani 1 1 d . . . . .
O3 O 1.02208(13) 0.40231(9) 0.22532(8) 0.0419(3) Uani 1 1 d . . . . .
C3 C 0.78859(18) 0.72995(11) 0.34630(11) 0.0320(4) Uani 1 1 d . . . . .
O5 O 0.65101(13) 0.56181(8) 0.56310(7) 0.0398(3) Uani 1 1 d . . . . .
C5 C 0.7124(2) 0.76610(13) 0.21529(13) 0.0486(6) Uani 1 1 d . . . . .
H5 H 0.653177 0.793559 0.175256 0.058 Uiso 1 1 calc R U . . .
C8 C 0.88004(17) 0.67939(11) 0.32956(10) 0.0308(4) Uani 1 1 d . . . . .
O8 O 0.52974(15) 0.62099(12) 0.90941(9) 0.0578(4) Uani 1 1 d . . . . .
C7 C 0.8926(2) 0.67450(12) 0.25644(11) 0.0391(5) Uani 1 1 d . . . . .
H7 H 0.956809 0.641698 0.245159 0.047 Uiso 1 1 calc R U . . .
O7 O 0.46329(13) 0.59601(9) 0.78460(8) 0.0411(3) Uani 1 1 d . . . . .
C6 C 0.8081(2) 0.71922(13) 0.20058(12) 0.0481(6) Uani 1 1 d . . . . .
O6 O 0.40791(13) 0.48638(8) 0.69727(7) 0.0364(3) Uani 1 1 d . . . . .
C9 C 0.95572(17) 0.63373(11) 0.39939(10) 0.0312(4) Uani 1 1 d . . . . .
H9 H 1.044741 0.652010 0.413517 0.037 Uiso 1 1 calc R U . . .
C10 C 0.85502(17) 0.51109(11) 0.43737(10) 0.0315(4) Uani 1 1 d . . . . .
C11 C 0.94290(17) 0.53842(12) 0.39421(10) 0.0309(4) Uani 1 1 d . . . . .
C12 C 0.99473(17) 0.48393(12) 0.35669(11) 0.0335(4) Uani 1 1 d . . . . .
H12 H 0.980458 0.424683 0.359964 0.040 Uiso 1 1 calc R U . . .
C13 C 1.11939(18) 0.44876(12) 0.27591(11) 0.0364(4) Uani 1 1 d . . . . .
H13 H 1.174712 0.409825 0.313304 0.044 Uiso 1 1 calc R U . . .
C15 C 1.1407(2) 0.46770(13) 0.15524(13) 0.0420(5) Uani 1 1 d . . . . .
C14 C 1.18885(19) 0.48960(13) 0.22651(13) 0.0407(5) Uani 1 1 d . . . . .
H14 H 1.258212 0.526305 0.243863 0.049 Uiso 1 1 calc R U . . .
C17 C 1.1779(3) 0.49052(17) 0.08501(15) 0.0645(7) Uani 1 1 d . . . . .
H17A H 1.191202 0.438454 0.058917 0.097 Uiso 1 1 calc R U . . .
H17B H 1.254888 0.523756 0.098736 0.097 Uiso 1 1 calc R U . . .
H17C H 1.111814 0.524251 0.051486 0.097 Uiso 1 1 calc R U . . .
C16 C 1.0338(2) 0.41135(13) 0.15280(12) 0.0409(5) Uani 1 1 d . . . . .
C18 C 0.60255(18) 0.33840(12) 0.55749(11) 0.0349(4) Uani 1 1 d . . . . .
H18 H 0.543185 0.315303 0.510822 0.042 Uiso 1 1 calc R U . . .
C19 C 0.7003(2) 0.27239(12) 0.59397(12) 0.0418(5) Uani 1 1 d . . . . .
H19A H 0.673811 0.214760 0.574496 0.050 Uiso 1 1 calc R U . . .
H19B H 0.781048 0.285609 0.583923 0.050 Uiso 1 1 calc R U . . .
C20 C 0.70990(18) 0.27830(11) 0.67732(12) 0.0365(4) Uani 1 1 d . . . . .
C21 C 0.7969(2) 0.24178(13) 0.73771(15) 0.0521(6) Uani 1 1 d . . . . .
H21 H 0.865935 0.211837 0.729392 0.063 Uiso 1 1 calc R U . . .
C22 C 0.7828(3) 0.24910(14) 0.81009(15) 0.0599(7) Uani 1 1 d . . . . .
H22 H 0.842986 0.225207 0.851817 0.072 Uiso 1 1 calc R U . . .
C23 C 0.6798(3) 0.29180(13) 0.82148(12) 0.0526(6) Uani 1 1 d . . . . .
C24 C 0.5937(2) 0.33090(12) 0.76243(11) 0.0411(5) Uani 1 1 d . . . . .
H24 H 0.524851 0.360986 0.770758 0.049 Uiso 1 1 calc R U . . .
C25 C 0.61166(18) 0.32459(11) 0.69053(10) 0.0315(4) Uani 1 1 d . . . . .
C26 C 0.53323(17) 0.36390(11) 0.61814(10) 0.0312(4) Uani 1 1 d . . . . .
H26 H 0.446186 0.341621 0.604728 0.037 Uiso 1 1 calc R U . . .
C27 C 0.53585(17) 0.45962(12) 0.61747(10) 0.0307(4) Uani 1 1 d . . . . .
C28 C 0.61936(18) 0.48790(12) 0.57138(10) 0.0326(4) Uani 1 1 d . . . . .
C29 C 0.47904(18) 0.51416(12) 0.65189(10) 0.0342(4) Uani 1 1 d . . . . .
H29 H 0.487800 0.573460 0.644960 0.041 Uiso 1 1 calc R U . . .
C30 C 0.36191(18) 0.55139(12) 0.73565(11) 0.0342(4) Uani 1 1 d . . . . .
H30 H 0.306954 0.591168 0.698933 0.041 Uiso 1 1 calc R U . . .
C31 C 0.29400(18) 0.51305(12) 0.78729(11) 0.0356(4) Uani 1 1 d . . . . .
H31 H 0.221865 0.478556 0.771324 0.043 Uiso 1 1 calc R U . . .
C32 C 0.34790(18) 0.53365(13) 0.85822(12) 0.0378(4) Uani 1 1 d . . . . .
C33 C 0.45664(19) 0.58738(13) 0.85781(11) 0.0392(5) Uani 1 1 d . . . . .
C34 C 0.3160(2) 0.51072(16) 0.92998(13) 0.0535(6) Uani 1 1 d . . . . .
H34A H 0.236725 0.480049 0.917899 0.080 Uiso 1 1 calc R U . . .
H34B H 0.308880 0.562643 0.958040 0.080 Uiso 1 1 calc R U . . .
H34C H 0.381523 0.474474 0.960965 0.080 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 C6 1.751(2) . ?
C1 N1 1.456(2) . ?
C1 C2 1.532(3) . ?
C1 C9 1.565(2) . ?
O1 C10 1.241(2) . ?
N1 C10 1.345(2) . ?
Cl2 C23 1.744(2) . ?
N2 C28 1.341(2) . ?
N2 C18 1.454(2) . ?
C2 C3 1.510(3) . ?
O2 C12 1.368(2) . ?
O2 C13 1.417(2) . ?
C4 C3 1.384(3) . ?
C4 C5 1.388(3) . ?
O4 C16 1.192(3) . ?
O3 C16 1.379(2) . ?
O3 C13 1.426(2) . ?
C3 C8 1.392(3) . ?
O5 C28 1.236(2) . ?
C5 C6 1.384(3) . ?
C8 C7 1.388(3) . ?
C8 C9 1.513(3) . ?
O8 C33 1.195(2) . ?
C7 C6 1.385(3) . ?
O7 C33 1.372(2) . ?
O7 C30 1.427(2) . ?
O6 C29 1.368(2) . ?
O6 C30 1.414(2) . ?
C9 C11 1.507(2) . ?
C10 C11 1.481(3) . ?
C11 C12 1.326(3) . ?
C13 C14 1.488(3) . ?
C15 C14 1.319(3) . ?
C15 C16 1.477(3) . ?
C15 C17 1.500(3) . ?
C18 C19 1.525(3) . ?
C18 C26 1.569(2) . ?
C19 C20 1.507(3) . ?
C20 C21 1.387(3) . ?
C20 C25 1.391(3) . ?
C21 C22 1.384(4) . ?
C22 C23 1.396(4) . ?
C23 C24 1.384(3) . ?
C24 C25 1.390(3) . ?
C25 C26 1.513(3) . ?
C26 C27 1.506(3) . ?
C27 C29 1.324(3) . ?
C27 C28 1.486(3) . ?
C30 C31 1.491(3) . ?
C31 C32 1.319(3) . ?
C32 C33 1.481(3) . ?
C32 C34 1.498(3) . ?

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 C1 C2 113.19(16) . . ?
N1 C1 C9 103.35(14) . . ?
C2 C1 C9 106.69(15) . . ?
C10 N1 C1 115.04(15) . . ?
C28 N2 C18 115.70(15) . . ?
C3 C2 C1 103.98(15) . . ?
C12 O2 C13 115.56(14) . . ?
C3 C4 C5 119.4(2) . . ?
C16 O3 C13 108.78(15) . . ?
C4 C3 C8 120.23(18) . . ?
C4 C3 C2 128.74(18) . . ?
C8 C3 C2 110.93(17) . . ?
C6 C5 C4 119.3(2) . . ?
C7 C8 C3 121.03(18) . . ?
C7 C8 C9 127.85(17) . . ?
C3 C8 C9 111.12(16) . . ?
C6 C7 C8 117.49(19) . . ?
C33 O7 C30 109.00(15) . . ?
C5 C6 C7 122.4(2) . . ?
C5 C6 Cl1 119.53(17) . . ?
C7 C6 Cl1 118.12(19) . . ?
C29 O6 C30 114.85(14) . . ?
C11 C9 C8 113.38(15) . . ?
C11 C9 C1 103.44(14) . . ?
C8 C9 C1 103.63(15) . . ?
O1 C10 N1 126.03(17) . . ?
O1 C10 C11 126.58(17) . . ?
N1 C10 C11 107.38(16) . . ?
C12 C11 C10 122.31(17) . . ?
C12 C11 C9 128.96(17) . . ?
C10 C11 C9 108.69(15) . . ?
C11 C12 O2 120.35(17) . . ?
O2 C13 O3 110.11(15) . . ?
O2 C13 C14 109.34(16) . . ?
O3 C13 C14 104.80(16) . . ?
C14 C15 C16 107.33(19) . . ?
C14 C15 C17 131.0(2) . . ?
C16 C15 C17 121.7(2) . . ?
C15 C14 C13 110.52(18) . . ?
O4 C16 O3 121.6(2) . . ?
O4 C16 C15 129.9(2) . . ?
O3 C16 C15 108.53(18) . . ?
N2 C18 C19 112.67(16) . . ?
N2 C18 C26 103.37(14) . . ?
C19 C18 C26 107.10(15) . . ?
C20 C19 C18 104.54(15) . . ?
C21 C20 C25 119.6(2) . . ?
C21 C20 C19 129.0(2) . . ?
C25 C20 C19 111.38(17) . . ?
C22 C21 C20 119.8(2) . . ?
C21 C22 C23 119.6(2) . . ?
C24 C23 C22 121.6(2) . . ?
C24 C23 Cl2 118.8(2) . . ?
C22 C23 Cl2 119.64(19) . . ?
C23 C24 C25 117.7(2) . . ?
C24 C25 C20 121.60(19) . . ?
C24 C25 C26 127.39(18) . . ?
C20 C25 C26 111.01(16) . . ?
C27 C26 C25 114.06(15) . . ?
C27 C26 C18 103.63(14) . . ?
C25 C26 C18 103.81(15) . . ?
C29 C27 C28 122.15(17) . . ?
C29 C27 C26 129.14(17) . . ?
C28 C27 C26 108.69(15) . . ?
O5 C28 N2 126.15(17) . . ?
O5 C28 C27 126.54(17) . . ?
N2 C28 C27 107.29(16) . . ?
C27 C29 O6 120.97(17) . . ?
O6 C30 O7 109.65(15) . . ?
O6 C30 C31 109.81(15) . . ?
O7 C30 C31 104.59(15) . . ?
C32 C31 C30 110.64(18) . . ?
C31 C32 C33 107.01(17) . . ?
C31 C32 C34 130.9(2) . . ?
C33 C32 C34 122.06(19) . . ?
O8 C33 O7 121.81(19) . . ?
O8 C33 C32 129.43(19) . . ?
O7 C33 C32 108.75(17) . . ?

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
C2 C1 N1 C10 128.57(17) . . . . ?
C9 C1 N1 C10 13.6(2) . . . . ?
N1 C1 C2 C3 -93.86(17) . . . . ?
C9 C1 C2 C3 19.13(19) . . . . ?
C5 C4 C3 C8 -1.5(3) . . . . ?
C5 C4 C3 C2 174.45(19) . . . . ?
C1 C2 C3 C4 166.76(19) . . . . ?
C1 C2 C3 C8 -17.0(2) . . . . ?
C3 C4 C5 C6 -2.0(3) . . . . ?
C4 C3 C8 C7 3.7(3) . . . . ?
C2 C3 C8 C7 -172.89(17) . . . . ?
C4 C3 C8 C9 -175.58(16) . . . . ?
C2 C3 C8 C9 7.8(2) . . . . ?
C3 C8 C7 C6 -2.3(3) . . . . ?
C9 C8 C7 C6 176.89(18) . . . . ?
C4 C5 C6 C7 3.5(3) . . . . ?
C4 C5 C6 Cl1 -176.15(16) . . . . ?
C8 C7 C6 C5 -1.3(3) . . . . ?
C8 C7 C6 Cl1 178.32(15) . . . . ?
C7 C8 C9 C11 -63.2(2) . . . . ?
C3 C8 C9 C11 116.08(18) . . . . ?
C7 C8 C9 C1 -174.61(18) . . . . ?
C3 C8 C9 C1 4.7(2) . . . . ?
N1 C1 C9 C11 -13.87(18) . . . . ?
C2 C1 C9 C11 -133.44(15) . . . . ?
N1 C1 C9 C8 104.67(15) . . . . ?
C2 C1 C9 C8 -14.90(19) . . . . ?
C1 N1 C10 O1 173.99(18) . . . . ?
C1 N1 C10 C11 -7.0(2) . . . . ?
O1 C10 C11 C12 -2.2(3) . . . . ?
N1 C10 C11 C12 178.86(18) . . . . ?
O1 C10 C11 C9 175.90(18) . . . . ?
N1 C10 C11 C9 -3.1(2) . . . . ?
C8 C9 C11 C12 77.0(2) . . . . ?
C1 C9 C11 C12 -171.41(19) . . . . ?
C8 C9 C11 C10 -100.85(17) . . . . ?
C1 C9 C11 C10 10.70(19) . . . . ?
C10 C11 C12 O2 175.44(16) . . . . ?
C9 C11 C12 O2 -2.2(3) . . . . ?
C13 O2 C12 C11 179.82(17) . . . . ?
C12 O2 C13 O3 61.0(2) . . . . ?
C12 O2 C13 C14 175.58(17) . . . . ?
C16 O3 C13 O2 119.49(17) . . . . ?
C16 O3 C13 C14 2.0(2) . . . . ?
C16 C15 C14 C13 0.8(2) . . . . ?
C17 C15 C14 C13 -178.9(2) . . . . ?
O2 C13 C14 C15 -119.78(19) . . . . ?
O3 C13 C14 C15 -1.8(2) . . . . ?
C13 O3 C16 O4 178.0(2) . . . . ?
C13 O3 C16 C15 -1.6(2) . . . . ?
C14 C15 C16 O4 -179.0(2) . . . . ?
C17 C15 C16 O4 0.7(4) . . . . ?
C14 C15 C16 O3 0.4(2) . . . . ?
C17 C15 C16 O3 -179.8(2) . . . . ?
C28 N2 C18 C19 -125.12(18) . . . . ?
C28 N2 C18 C26 -9.8(2) . . . . ?
N2 C18 C19 C20 98.38(17) . . . . ?
C26 C18 C19 C20 -14.6(2) . . . . ?
C18 C19 C20 C21 -169.59(19) . . . . ?
C18 C19 C20 C25 13.5(2) . . . . ?
C25 C20 C21 C22 2.3(3) . . . . ?
C19 C20 C21 C22 -174.4(2) . . . . ?
C20 C21 C22 C23 1.3(3) . . . . ?
C21 C22 C23 C24 -3.2(3) . . . . ?
C21 C22 C23 Cl2 176.06(17) . . . . ?
C22 C23 C24 C25 1.5(3) . . . . ?
Cl2 C23 C24 C25 -177.79(15) . . . . ?
C23 C24 C25 C20 2.2(3) . . . . ?
C23 C24 C25 C26 -177.94(18) . . . . ?
C21 C20 C25 C24 -4.1(3) . . . . ?
C19 C20 C25 C24 173.13(17) . . . . ?
C21 C20 C25 C26 176.00(17) . . . . ?
C19 C20 C25 C26 -6.8(2) . . . . ?
C24 C25 C26 C27 65.3(2) . . . . ?
C20 C25 C26 C27 -114.81(17) . . . . ?
C24 C25 C26 C18 177.35(18) . . . . ?
C20 C25 C26 C18 -2.8(2) . . . . ?
N2 C18 C26 C27 11.20(19) . . . . ?
C19 C18 C26 C27 130.39(16) . . . . ?
N2 C18 C26 C25 -108.25(16) . . . . ?
C19 C18 C26 C25 10.94(19) . . . . ?
C25 C26 C27 C29 -75.9(3) . . . . ?
C18 C26 C27 C29 172.0(2) . . . . ?
C25 C26 C27 C28 102.53(17) . . . . ?
C18 C26 C27 C28 -9.63(19) . . . . ?
C18 N2 C28 O5 -177.70(18) . . . . ?
C18 N2 C28 C27 3.9(2) . . . . ?
C29 C27 C28 O5 4.4(3) . . . . ?
C26 C27 C28 O5 -174.19(18) . . . . ?
C29 C27 C28 N2 -177.26(18) . . . . ?
C26 C27 C28 N2 4.2(2) . . . . ?
C28 C27 C29 O6 -176.47(16) . . . . ?
C26 C27 C29 O6 1.8(3) . . . . ?
C30 O6 C29 C27 174.63(17) . . . . ?
C29 O6 C30 O7 -61.5(2) . . . . ?
C29 O6 C30 C31 -175.90(16) . . . . ?
C33 O7 C30 O6 -118.80(17) . . . . ?
C33 O7 C30 C31 -1.1(2) . . . . ?
O6 C30 C31 C32 118.41(18) . . . . ?
O7 C30 C31 C32 0.8(2) . . . . ?
C30 C31 C32 C33 -0.2(2) . . . . ?
C30 C31 C32 C34 -179.5(2) . . . . ?
C30 O7 C33 O8 -178.0(2) . . . . ?
C30 O7 C33 C32 1.0(2) . . . . ?
C31 C32 C33 O8 178.5(2) . . . . ?
C34 C32 C33 O8 -2.1(4) . . . . ?
C31 C32 C33 O7 -0.5(2) . . . . ?
C34 C32 C33 O7 178.88(19) . . . . ?

_refine_diff_density_max         0.466
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_t_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2087617'
loop_
_audit_author_name
_audit_author_address
'Yi Dong'
;Shanghai Jiaotong University
China
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-07-27 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         'C17 H13 Cl O5'
_chemical_formula_sum            'C17 H13 Cl O5'
_chemical_formula_weight         332.72

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'
O O 0.0492 0.0322 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.588(3)
_cell_length_b                   7.415(2)
_cell_length_c                   16.351(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.998(18)
_cell_angle_gamma                90
_cell_volume                     1498.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5990
_cell_measurement_theta_min      4.92
_cell_measurement_theta_max      68.34

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   0.5093
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    2.482
_shelx_estimated_absorpt_T_min   0.664
_shelx_estimated_absorpt_T_max   0.723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10523
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.915
_diffrn_reflns_theta_max         68.215
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2735
_reflns_number_gt                2360
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_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)+(0.0529P)²+0.4055P] 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         2735
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0950
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.45313(4) 0.34606(6) 0.07917(3) 0.03965(16) Uani 1 1 d . . . . .
C1 C 0.68896(13) 0.4544(2) 0.45348(11) 0.0299(4) Uani 1 1 d . . . . .
H1 H 0.692244 0.514179 0.508736 0.036 Uiso 1 1 calc R U . . .
O1 O 0.73269(9) 0.27095(16) 0.46212(7) 0.0303(3) Uani 1 1 d . . . . .
O2 O 0.67203(10) -0.01227(16) 0.46094(8) 0.0345(3) Uani 1 1 d . . . . .
C2 C 0.74877(13) 0.5623(2) 0.39701(11) 0.0324(4) Uani 1 1 d . . . . .
H2A H 0.748253 0.692744 0.409888 0.039 Uiso 1 1 calc R U . . .
H2B H 0.824647 0.521151 0.402754 0.039 Uiso 1 1 calc R U . . .
O4 O 0.25501(9) 0.13079(15) 0.26842(7) 0.0305(3) Uani 1 1 d . . . . .
C4 C 0.71317(14) 0.5459(2) 0.23269(11) 0.0316(4) Uani 1 1 d . . . . .
H4 H 0.781215 0.596964 0.228700 0.038 Uiso 1 1 calc R U . . .
O3 O 0.36055(9) 0.24545(15) 0.38858(8) 0.0287(3) Uani 1 1 d . . . . .
C3 C 0.68489(13) 0.5235(2) 0.31032(11) 0.0278(4) Uani 1 1 d . . . . .
O5 O 0.13759(11) 0.23330(17) 0.15688(8) 0.0380(3) Uani 1 1 d . . . . .
C5 C 0.64148(14) 0.4932(2) 0.16080(11) 0.0321(4) Uani 1 1 d . . . . .
H5 H 0.660009 0.507916 0.107525 0.039 Uiso 1 1 calc R U . . .
C7 C 0.51158(12) 0.3983(2) 0.24491(10) 0.0250(3) Uani 1 1 d . . . . .
H7 H 0.443119 0.348811 0.248822 0.030 Uiso 1 1 calc R U . . .
C6 C 0.54245(13) 0.4189(2) 0.16835(10) 0.0283(4) Uani 1 1 d . . . . .
C8 C 0.58407(12) 0.4524(2) 0.31553(10) 0.0243(3) Uani 1 1 d . . . . .
C9 C 0.57144(12) 0.4306(2) 0.40613(10) 0.0254(3) Uani 1 1 d . . . . .
H9 H 0.519436 0.518062 0.423431 0.030 Uiso 1 1 calc R U . . .
C10 C 0.54817(12) 0.2382(2) 0.42398(9) 0.0245(3) Uani 1 1 d . . . . .
C11 C 0.65247(13) 0.1465(2) 0.45068(10) 0.0267(4) Uani 1 1 d . . . . .
C12 C 0.45386(13) 0.1517(2) 0.41210(10) 0.0257(3) Uani 1 1 d . . . . .
H12 H 0.451902 0.024910 0.420058 0.031 Uiso 1 1 calc R U . . .
C13 C 0.26609(13) 0.1441(2) 0.35734(11) 0.0271(4) Uani 1 1 d . . . . .
H13 H 0.269145 0.022069 0.383771 0.033 Uiso 1 1 calc R U . . .
C14 C 0.16889(13) 0.2467(2) 0.37064(11) 0.0302(4) Uani 1 1 d . . . . .
H14 H 0.152160 0.274751 0.423445 0.036 Uiso 1 1 calc R U . . .
C15 C 0.10922(13) 0.2932(2) 0.29767(12) 0.0297(4) Uani 1 1 d . . . . .
C16 C 0.16343(13) 0.2219(2) 0.23150(11) 0.0287(4) Uani 1 1 d . . . . .
C17 C 0.00576(14) 0.3963(2) 0.27706(14) 0.0400(4) Uani 1 1 d . . . . .
H17A H 0.018757 0.511368 0.251201 0.060 Uiso 1 1 calc R U . . .
H17B H -0.021955 0.419106 0.328181 0.060 Uiso 1 1 calc R U . . .
H17C H -0.047456 0.326016 0.238261 0.060 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 C6 1.7482(17) . ?
C1 O1 1.464(2) . ?
C1 C2 1.525(2) . ?
C1 C9 1.543(2) . ?
O1 C11 1.355(2) . ?
O2 C11 1.208(2) . ?
C2 C3 1.518(2) . ?
O4 C16 1.373(2) . ?
O4 C13 1.437(2) . ?
C4 C3 1.392(3) . ?
C4 C5 1.394(3) . ?
O3 C12 1.3559(19) . ?
O3 C13 1.4171(19) . ?
C3 C8 1.392(2) . ?
O5 C16 1.204(2) . ?
C5 C6 1.390(2) . ?
C7 C8 1.387(2) . ?
C7 C6 1.388(2) . ?
C8 C9 1.528(2) . ?
C9 C10 1.496(2) . ?
C10 C12 1.331(2) . ?
C10 C11 1.469(2) . ?
C13 C14 1.492(2) . ?
C14 C15 1.328(3) . ?
C15 C16 1.482(3) . ?
C15 C17 1.492(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
O1 C1 C2 109.02(13) . . ?
O1 C1 C9 104.40(13) . . ?
C2 C1 C9 107.05(14) . . ?
C11 O1 C1 111.30(12) . . ?
C3 C2 C1 103.37(13) . . ?
C16 O4 C13 108.81(12) . . ?
C3 C4 C5 119.89(15) . . ?
C12 O3 C13 116.88(12) . . ?
C8 C3 C4 119.72(16) . . ?
C8 C3 C2 109.96(15) . . ?
C4 C3 C2 130.31(15) . . ?
C6 C5 C4 118.91(16) . . ?
C8 C7 C6 117.77(15) . . ?
C7 C6 C5 122.26(16) . . ?
C7 C6 Cl1 118.17(13) . . ?
C5 C6 Cl1 119.56(13) . . ?
C7 C8 C3 121.42(16) . . ?
C7 C8 C9 127.04(14) . . ?
C3 C8 C9 111.36(14) . . ?
C10 C9 C8 110.52(13) . . ?
C10 C9 C1 102.47(13) . . ?
C8 C9 C1 101.95(13) . . ?
C12 C10 C11 122.85(15) . . ?
C12 C10 C9 129.29(14) . . ?
C11 C10 C9 107.59(13) . . ?
O2 C11 O1 121.21(14) . . ?
O2 C11 C10 129.75(15) . . ?
O1 C11 C10 109.03(13) . . ?
C10 C12 O3 119.67(14) . . ?
O3 C13 O4 108.28(13) . . ?
O3 C13 C14 109.38(13) . . ?
O4 C13 C14 104.97(13) . . ?
C15 C14 C13 109.90(16) . . ?
C14 C15 C16 107.63(15) . . ?
C14 C15 C17 130.95(18) . . ?
C16 C15 C17 121.42(17) . . ?
O5 C16 O4 121.46(16) . . ?
O5 C16 C15 129.90(16) . . ?
O4 C16 C15 108.63(14) . . ?

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
C2 C1 O1 C11 -132.66(14) . . . . ?
C9 C1 O1 C11 -18.54(17) . . . . ?
O1 C1 C2 C3 87.58(15) . . . . ?
C9 C1 C2 C3 -24.80(17) . . . . ?
C5 C4 C3 C8 -1.5(2) . . . . ?
C5 C4 C3 C2 177.38(16) . . . . ?
C1 C2 C3 C8 16.62(18) . . . . ?
C1 C2 C3 C4 -162.30(16) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C8 C7 C6 C5 -0.9(2) . . . . ?
C8 C7 C6 Cl1 178.47(11) . . . . ?
C4 C5 C6 C7 1.2(2) . . . . ?
C4 C5 C6 Cl1 -178.17(12) . . . . ?
C6 C7 C8 C3 -0.6(2) . . . . ?
C6 C7 C8 C9 -175.27(14) . . . . ?
C4 C3 C8 C7 1.8(2) . . . . ?
C2 C3 C8 C7 -177.29(14) . . . . ?
C4 C3 C8 C9 177.22(14) . . . . ?
C2 C3 C8 C9 -1.83(18) . . . . ?
C7 C8 C9 C10 53.3(2) . . . . ?
C3 C8 C9 C10 -121.84(14) . . . . ?
C7 C8 C9 C1 161.65(15) . . . . ?
C3 C8 C9 C1 -13.49(17) . . . . ?
O1 C1 C9 C10 22.40(16) . . . . ?
C2 C1 C9 C10 137.91(13) . . . . ?
O1 C1 C9 C8 -92.04(14) . . . . ?
C2 C1 C9 C8 23.47(16) . . . . ?
C8 C9 C10 C12 -85.5(2) . . . . ?
C1 C9 C10 C12 166.54(17) . . . . ?
C8 C9 C10 C11 88.64(15) . . . . ?
C1 C9 C10 C11 -19.37(16) . . . . ?
C1 O1 C11 O2 -174.86(15) . . . . ?
C1 O1 C11 C10 6.35(17) . . . . ?
C12 C10 C11 O2 5.0(3) . . . . ?
C9 C10 C11 O2 -169.58(17) . . . . ?
C12 C10 C11 O1 -176.37(15) . . . . ?
C9 C10 C11 O1 9.07(17) . . . . ?
C11 C10 C12 O3 179.05(14) . . . . ?
C9 C10 C12 O3 -7.7(3) . . . . ?
C13 O3 C12 C10 164.95(15) . . . . ?
C12 O3 C13 O4 -91.47(15) . . . . ?
C12 O3 C13 C14 154.67(14) . . . . ?
C16 O4 C13 O3 -114.51(14) . . . . ?
C16 O4 C13 C14 2.24(16) . . . . ?
O3 C13 C14 C15 114.31(15) . . . . ?
O4 C13 C14 C15 -1.69(17) . . . . ?
C13 C14 C15 C16 0.51(18) . . . . ?
C13 C14 C15 C17 -179.70(16) . . . . ?
C13 O4 C16 O5 178.56(15) . . . . ?
C13 O4 C16 C15 -2.01(16) . . . . ?
C14 C15 C16 O5 -179.71(17) . . . . ?
C17 C15 C16 O5 0.5(3) . . . . ?
C14 C15 C16 O4 0.93(18) . . . . ?
C17 C15 C16 O4 -178.88(14) . . . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.046

