# 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_20190627ZH_ZNZ4668_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1945794'
loop_
_audit_author_name
_audit_author_address
'Bo Xu'
;Donghua University
China
;
_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2020-12-18 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            'C20 H14 Cl2 O4'
_chemical_formula_weight         389.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.4191(2)
_cell_length_b                   10.2779(2)
_cell_length_c                   11.5069(3)
_cell_angle_alpha                71.5840(10)
_cell_angle_beta                 72.7130(10)
_cell_angle_gamma                72.0840(10)
_cell_volume                     876.57(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    7248
_cell_measurement_theta_min      4.93
_cell_measurement_theta_max      60.40

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    2.338
_shelx_estimated_absorpt_T_min   0.706
_shelx_estimated_absorpt_T_max   0.783
_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      193(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\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            10859
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.925
_diffrn_reflns_theta_max         52.995
_diffrn_reflns_theta_full        52.995
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3029
_reflns_number_gt                2669
_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 2014/5 (Sheldrick, 2014)'
_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)+(0.0547P)²+0.3277P] 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         3029
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.1056
_refine_ls_wR_factor_gt          0.1000
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
C1 C 0.6208(3) 0.9544(3) 0.11182(19) 0.0562(6) Uani 1 1 d . . . . .
H1A H 0.709382 0.875337 0.084951 0.084 Uiso 1 1 calc R U . . .
H1B H 0.622376 1.039854 0.043012 0.084 Uiso 1 1 calc R U . . .
H1C H 0.508383 0.932627 0.134495 0.084 Uiso 1 1 calc R U . . .
C2 C 0.6501(2) 0.86770(19) 0.32048(17) 0.0368(4) Uani 1 1 d . . . . .
C3 C 0.6968(2) 0.89258(18) 0.42503(16) 0.0330(4) Uani 1 1 d . . . . .
C4 C 0.7253(2) 1.01986(18) 0.41692(17) 0.0350(4) Uani 1 1 d . . . . .
H4 H 0.715148 1.093564 0.342888 0.042 Uiso 1 1 calc R U . . .
C5 C 0.7692(2) 1.04337(17) 0.51609(17) 0.0342(4) Uani 1 1 d . . . . .
C6 C 0.8012(2) 1.17435(18) 0.5078(2) 0.0402(4) Uani 1 1 d . . . . .
H6 H 0.791516 1.248201 0.433767 0.048 Uiso 1 1 calc R U . . .
C7 C 0.8452(2) 1.19629(19) 0.6033(2) 0.0427(5) Uani 1 1 d . . . . .
H7 H 0.866820 1.284183 0.596315 0.051 Uiso 1 1 calc R U . . .
C8 C 0.8580(2) 1.0868(2) 0.71238(19) 0.0403(4) Uani 1 1 d . . . . .
C9 C 0.8318(2) 0.95742(18) 0.72547(17) 0.0366(4) Uani 1 1 d . . . . .
H9 H 0.844331 0.884937 0.799932 0.044 Uiso 1 1 calc R U . . .
C10 C 0.7857(2) 0.93274(17) 0.62699(16) 0.0319(4) Uani 1 1 d . . . . .
C11 C 0.7575(2) 0.80009(17) 0.63423(16) 0.0307(4) Uani 1 1 d . . . . .
C12 C 0.7122(2) 0.78141(17) 0.53609(16) 0.0306(4) Uani 1 1 d . . . . .
C13 C 0.6826(2) 0.63954(17) 0.55176(15) 0.0312(4) Uani 1 1 d . . . . .
C14 C 0.4930(3) 0.4923(2) 0.66733(19) 0.0455(5) Uani 1 1 d . . . . .
H14A H 0.518013 0.453569 0.594483 0.068 Uiso 1 1 calc R U . . .
H14B H 0.372034 0.499810 0.709568 0.068 Uiso 1 1 calc R U . . .
H14C H 0.564690 0.429873 0.725871 0.068 Uiso 1 1 calc R U . . .
C15 C 0.7838(2) 0.67897(17) 0.74598(16) 0.0316(4) Uani 1 1 d . . . . .
C16 C 0.6663(3) 0.6736(2) 0.86051(18) 0.0442(5) Uani 1 1 d . . . . .
H16 H 0.567995 0.749246 0.869083 0.053 Uiso 1 1 calc R U . . .
C17 C 0.6907(3) 0.5597(2) 0.96205(19) 0.0521(5) Uani 1 1 d . . . . .
H17 H 0.609744 0.556630 1.040047 0.063 Uiso 1 1 calc R U . . .
C18 C 0.8338(3) 0.4504(2) 0.94889(18) 0.0457(5) Uani 1 1 d . . . . .
C19 C 0.9524(3) 0.45299(19) 0.83703(19) 0.0435(5) Uani 1 1 d . . . . .
H19 H 1.050886 0.377370 0.829285 0.052 Uiso 1 1 calc R U . . .
C20 C 0.9265(2) 0.56755(18) 0.73551(17) 0.0370(4) Uani 1 1 d . . . . .
H20 H 1.007583 0.569751 0.657668 0.044 Uiso 1 1 calc R U . . .
Cl1 Cl 0.90901(8) 1.11802(6) 0.83432(5) 0.0597(2) Uani 1 1 d . . . . .
Cl2 Cl 0.86135(10) 0.30361(6) 1.07529(5) 0.0716(2) Uani 1 1 d . . . . .
O1 O 0.65358(18) 0.97684(15) 0.21917(12) 0.0482(4) Uani 1 1 d . . . . .
O2 O 0.6141(2) 0.76275(15) 0.32415(13) 0.0556(4) Uani 1 1 d . . . . .
O3 O 0.78490(17) 0.54464(13) 0.51203(13) 0.0431(3) Uani 1 1 d . . . . .
O4 O 0.52862(15) 0.63035(12) 0.62624(11) 0.0352(3) Uani 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
C1 O1 1.441(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O2 1.192(2) . ?
C2 O1 1.339(2) . ?
C2 C3 1.485(3) . ?
C3 C4 1.371(2) . ?
C3 C12 1.428(2) . ?
C4 C5 1.406(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.421(2) . ?
C5 C10 1.425(2) . ?
C6 C7 1.359(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.403(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.369(2) . ?
C8 Cl1 1.727(2) . ?
C9 C10 1.415(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.428(2) . ?
C11 C12 1.377(2) . ?
C11 C15 1.497(2) . ?
C12 C13 1.500(2) . ?
C13 O3 1.197(2) . ?
C13 O4 1.337(2) . ?
C14 O4 1.442(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C20 1.387(3) . ?
C15 C16 1.390(3) . ?
C16 C17 1.382(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.373(3) . ?
C18 Cl2 1.7447(19) . ?
C19 C20 1.387(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

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 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 122.81(17) . . ?
O2 C2 C3 124.71(16) . . ?
O1 C2 C3 112.48(15) . . ?
C4 C3 C12 119.54(16) . . ?
C4 C3 C2 121.31(16) . . ?
C12 C3 C2 119.15(15) . . ?
C3 C4 C5 121.26(16) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 121.60(17) . . ?
C4 C5 C10 119.55(15) . . ?
C6 C5 C10 118.84(17) . . ?
C7 C6 C5 121.46(18) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 118.78(16) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C9 C8 C7 122.63(18) . . ?
C9 C8 Cl1 119.24(16) . . ?
C7 C8 Cl1 118.13(14) . . ?
C8 C9 C10 119.35(17) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C9 C10 C5 118.92(15) . . ?
C9 C10 C11 122.21(16) . . ?
C5 C10 C11 118.86(16) . . ?
C12 C11 C10 120.04(15) . . ?
C12 C11 C15 119.62(14) . . ?
C10 C11 C15 120.30(15) . . ?
C11 C12 C3 120.73(15) . . ?
C11 C12 C13 116.74(15) . . ?
C3 C12 C13 122.52(15) . . ?
O3 C13 O4 124.53(15) . . ?
O3 C13 C12 125.72(16) . . ?
O4 C13 C12 109.53(14) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 118.68(17) . . ?
C20 C15 C11 119.80(15) . . ?
C16 C15 C11 121.51(16) . . ?
C17 C16 C15 120.79(19) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 119.25(19) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C19 C18 C17 121.25(18) . . ?
C19 C18 Cl2 119.34(17) . . ?
C17 C18 Cl2 119.37(16) . . ?
C18 C19 C20 119.06(19) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C15 C20 C19 120.97(17) . . ?
C15 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C2 O1 C1 114.75(16) . . ?
C13 O4 C14 116.02(14) . . ?

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.037



