# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_cxy1916
_database_code_depnum_ccdc_archive 'CCDC 2175166'
loop_
_audit_author_name
_audit_author_address
'Gen-Qiang Chen'
;Southern university of science and technology
China
;
_audit_update_record             
;
2022-05-26 deposited with the CCDC.	2024-07-30 downloaded from the CCDC.
;
_audit_creation_date             2022-05-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H10 Cl F O'
_chemical_formula_sum            'C10 H10 Cl F O'
_chemical_formula_weight         200.63
_chemical_absolute_configuration ad
_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 0.0033 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'
F F 0.0171 0.0103 '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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   4.9064(3)
_cell_length_b                   9.6220(5)
_cell_length_c                   19.4077(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     916.23(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.386
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7027
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1009 before and 0.0500 after correction.
The Ratio of minimum to maximum transmission is 0.9423.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13580
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.273
_diffrn_reflns_theta_min         2.363
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON II area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2145
_reflns_number_total             2281
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2014'
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 835 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0259
_refine_ls_restrained_S_all      1.052
_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)+(0.0261P)²+0.3497P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0603
_refine_ls_wR_factor_ref         0.0624
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Cl1 Cl -0.02166(10) 0.57135(5) 0.19706(2) 0.02095(13) Uani 1 1 d . . . . .
F1 F 0.5316(3) 0.47524(12) 0.51482(6) 0.0237(3) Uani 1 1 d . . . . .
O1 O 0.7295(3) 0.72919(14) 0.47041(7) 0.0163(3) Uani 1 1 d . . . . .
H1 H 0.873835 0.753959 0.490177 0.025 Uiso 1 1 calc R U . . .
C1 C 0.2029(4) 0.5811(2) 0.26651(9) 0.0134(3) Uani 1 1 d . . . . .
C2 C 0.2908(4) 0.70996(19) 0.28905(10) 0.0147(4) Uani 1 1 d . . . . .
H2 H 0.226071 0.792728 0.267973 0.018 Uiso 1 1 calc R U . . .
C3 C 0.4755(4) 0.71567(18) 0.34314(9) 0.0144(4) Uani 1 1 d . . . . .
H3 H 0.539707 0.803400 0.358672 0.017 Uiso 1 1 calc R U . . .
C4 C 0.5687(3) 0.59460(19) 0.37513(9) 0.0117(3) Uani 1 1 d . . . . .
C5 C 0.7784(4) 0.60547(18) 0.43215(9) 0.0127(4) Uani 1 1 d . . . . .
H5 H 0.962383 0.613440 0.410335 0.015 Uiso 1 1 calc R U . . .
C6 C 0.7787(4) 0.4780(2) 0.47774(10) 0.0172(4) Uani 1 1 d . . . . .
H6 H 0.935320 0.482989 0.510635 0.021 Uiso 1 1 calc R U . . .
C7 C 0.2915(4) 0.45942(18) 0.29733(10) 0.0127(3) Uani 1 1 d . . . . .
H7 H 0.228367 0.372110 0.280969 0.015 Uiso 1 1 calc R U . . .
C8 C 0.4740(4) 0.46535(17) 0.35256(8) 0.0111(3) Uani 1 1 d . . . . .
C9 C 0.5548(4) 0.33153(18) 0.38792(9) 0.0134(4) Uani 1 1 d . . . . .
H9A H 0.596204 0.260744 0.352406 0.016 Uiso 1 1 calc R U . . .
H9B H 0.398381 0.297322 0.415323 0.016 Uiso 1 1 calc R U . . .
C10 C 0.8003(4) 0.3470(2) 0.43503(10) 0.0159(4) Uani 1 1 d . . . . .
H10A H 0.812165 0.265417 0.465940 0.019 Uiso 1 1 calc R U . . .
H10B H 0.968632 0.350352 0.406957 0.019 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 1.7434(18) . ?
F1 C6 1.410(2) . ?
O1 H1 0.8400 . ?
O1 C5 1.423(2) . ?
C1 C2 1.383(3) . ?
C1 C7 1.385(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(2) . ?
C4 C5 1.515(2) . ?
C4 C8 1.398(2) . ?
C5 H5 1.0000 . ?
C5 C6 1.512(3) . ?
C6 H6 1.0000 . ?
C6 C10 1.512(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.398(2) . ?
C8 C9 1.512(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.520(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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
C5 O1 H1 109.5 . . ?
C2 C1 Cl1 119.34(14) . . ?
C2 C1 C7 121.55(16) . . ?
C7 C1 Cl1 119.11(15) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.57(16) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.12(16) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 119.30(16) . . ?
C3 C4 C8 119.59(16) . . ?
C8 C4 C5 121.08(16) . . ?
O1 C5 C4 108.93(15) . . ?
O1 C5 H5 108.0 . . ?
O1 C5 C6 111.90(15) . . ?
C4 C5 H5 108.0 . . ?
C6 C5 C4 111.86(16) . . ?
C6 C5 H5 108.0 . . ?
F1 C6 C5 108.25(15) . . ?
F1 C6 H6 109.6 . . ?
F1 C6 C10 108.90(16) . . ?
C5 C6 H6 109.6 . . ?
C5 C6 C10 110.80(15) . . ?
C10 C6 H6 109.6 . . ?
C1 C7 H7 120.1 . . ?
C1 C7 C8 119.84(16) . . ?
C8 C7 H7 120.1 . . ?
C4 C8 C9 121.89(16) . . ?
C7 C8 C4 119.31(15) . . ?
C7 C8 C9 118.76(15) . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C8 C9 C10 113.40(15) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C6 C10 C9 110.87(16) . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?

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
Cl1 C1 C2 C3 -178.19(14) . . . . ?
Cl1 C1 C7 C8 179.27(14) . . . . ?
F1 C6 C10 C9 56.20(19) . . . . ?
O1 C5 C6 F1 54.5(2) . . . . ?
O1 C5 C6 C10 173.82(16) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C1 C7 C8 C4 -1.2(3) . . . . ?
C1 C7 C8 C9 176.50(16) . . . . ?
C2 C1 C7 C8 0.0(3) . . . . ?
C2 C3 C4 C5 177.71(17) . . . . ?
C2 C3 C4 C8 -0.2(3) . . . . ?
C3 C4 C5 O1 34.5(2) . . . . ?
C3 C4 C5 C6 158.76(16) . . . . ?
C3 C4 C8 C7 1.3(2) . . . . ?
C3 C4 C8 C9 -176.32(17) . . . . ?
C4 C5 C6 F1 -68.08(19) . . . . ?
C4 C5 C6 C10 51.3(2) . . . . ?
C4 C8 C9 C10 -15.9(2) . . . . ?
C5 C4 C8 C7 -176.60(16) . . . . ?
C5 C4 C8 C9 5.8(3) . . . . ?
C5 C6 C10 C9 -62.8(2) . . . . ?
C7 C1 C2 C3 1.1(3) . . . . ?
C7 C8 C9 C10 166.43(16) . . . . ?
C8 C4 C5 O1 -147.57(16) . . . . ?
C8 C4 C5 C6 -23.3(2) . . . . ?
C8 C9 C10 C6 43.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cxy3548_0m
_database_code_depnum_ccdc_archive 'CCDC 2175167'
loop_
_audit_author_name
_audit_author_address
'Gen-Qiang Chen'
;Southern university of science and technology
China
;
_audit_update_record             
;
2022-05-26 deposited with the CCDC.	2024-07-30 downloaded from the CCDC.
;
_audit_creation_date             2022-05-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H8 Cl2 O2'
_chemical_formula_sum            'C9 H8 Cl2 O2'
_chemical_formula_weight         219.05
_chemical_absolute_configuration ad
_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'
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.7032(9)
_cell_length_b                   4.8645(5)
_cell_length_c                   11.7272(12)
_cell_angle_alpha                90
_cell_angle_beta                 110.291(3)
_cell_angle_gamma                90
_cell_volume                     465.68(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8633
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.21
_cell_measurement_theta_min      4.02
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.971
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.3653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1429 before and 0.0913 after correction.
The Ratio of minimum to maximum transmission is 0.4847.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7937
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.281
_diffrn_reflns_theta_min         4.019
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON II area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.11
_diffrn_source_power             0.05550000000000001
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                1803
_reflns_number_total             1806
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2014'
_refine_diff_density_max         1.023
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details 
;
 Flack x determined using 766 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1806
_refine_ls_number_restraints     35
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.160
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0233P)²+1.6071P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1328
_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 O(H) groups
2. Restrained distances
 C2-C7 \\sim C2A-C7A
 with sigma of 0.04
 O2-C8 \\sim O2A-C8A
 with sigma of 0.04
 C2-C8 \\sim C2A-C8A
 with sigma of 0.02
 C4-C7 \\sim C4A-C7A
 with sigma of 0.04
 O2-C9 \\sim O2A-C9A
 with sigma of 0.02
 O2-C6 \\sim O2A-C6A
 with sigma of 0.04
 C5-C8 \\sim C5A-C8A
 with sigma of 0.04
 C5-C7 \\sim C5A-C7A
 with sigma of 0.02
 C7-C8 \\sim C7A-C8A
 with sigma of 0.02
 C8-C9 \\sim C8A-C9A
 with sigma of 0.02
 C3-C8 \\sim C3A-C8A
 with sigma of 0.04
 C6-C8 \\sim C6A-C8A
 with sigma of 0.04
 Cl1-C7 \\sim Cl1A-C7A
 with sigma of 0.04
 C7-C9 \\sim C7A-C9A
 with sigma of 0.04
 O1-C8 \\sim O1A-C8A
 with sigma of 0.04
 O1-C2 \\sim O1A-C2A
 with sigma of 0.02
 O1-C1 \\sim O1A-C1A
 with sigma of 0.02
 Cl2-C6 \\sim Cl2A-C6A
 with sigma of 0.02
 Cl1-C5 \\sim Cl1A-C5A
 with sigma of 0.02
 C2-C3 \\sim C2A-C3A
 with sigma of 0.02
 C1-C6 \\sim C1A-C6A
 with sigma of 0.02
 Cl1-C4 \\sim Cl1A-C4A
 with sigma of 0.04
 C3-C4 \\sim C3A-C4A
 with sigma of 0.02
 Cl2-C1 \\sim Cl2A-C1A
 with sigma of 0.04
 Cl2-C9 \\sim Cl2A-C9A
 with sigma of 0.04
 C4-C5 \\sim C4A-C5A
 with sigma of 0.02
 O1-C3 \\sim O1A-C3A
 with sigma of 0.04
 O1-C6 \\sim O1A-C6A
 with sigma of 0.04
 C1-C2 \\sim C1A-C2A
 with sigma of 0.04
 C1-C9 \\sim C1A-C9A
 with sigma of 0.04
 C6-C9 \\sim C6A-C9A
 with sigma of 0.02
 C2-C4 \\sim C2A-C4A
 with sigma of 0.04
 C2-C9 \\sim C2A-C9A
 with sigma of 0.04
 C3-C5 \\sim C3A-C5A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(O2A) = Uanis(O2)
Uanis(C5) = Uanis(C5A)
Uanis(C1A) = Uanis(C1)
Uanis(C3A) = Uanis(C3)
Uanis(C8) = Uanis(C8A)
Uanis(C6A) = Uanis(C6)
Uanis(Cl1) = Uanis(Cl1A)
Uanis(C4) = Uanis(C4A)
Uanis(C2) = Uanis(C2A)
Uanis(C7) = Uanis(C7A)
Uanis(C9) = Uanis(C9A)
Uanis(Cl2) = Uanis(Cl2A)
Uanis(O1) = Uanis(O1A)
4. Others
 Sof(C8A)=Sof(Cl1A)=Sof(C5A)=Sof(C4A)=Sof(H4A)=Sof(C7A)=Sof(H7A)=Sof(C3A)=
 Sof(H3A)=Sof(C2A)=Sof(C9A)=Sof(H9A)=Sof(O1A)=Sof(O2A)=Sof(H2A)=Sof(C6A)=
 Sof(H6A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(Cl2A)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(O1)=Sof(O2)=Sof(H2)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(C2)=
 Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=
 Sof(C8)=Sof(C9)=Sof(H9)=FVAR(1)
5.a Riding coordinates:
 O2A(H2A)
5.b Ternary CH refined with riding coordinates:
 C6(H6), C9(H9), C9A(H9A), C6A(H6A)
5.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C1A(H1AA,H1AB)
5.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C4A(H4A), C7A(H7A), C3A(H3A)
5.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Cl1 Cl 0.6503(2) 0.7828(4) 0.16339(19) 0.0372(5) Uani 0.930(3) 1 d D . P A 1
Cl2 Cl 0.1441(2) 0.5547(3) 0.46386(14) 0.0219(4) Uani 0.930(3) 1 d D . P A 1
O1 O 0.0069(5) 0.4783(10) 0.1836(4) 0.0223(11) Uani 0.930(3) 1 d D . P A 1
O2 O 0.4325(6) 0.2115(10) 0.4601(4) 0.0206(10) Uani 0.930(3) 1 d D . P A 1
H2 H 0.471309 0.052412 0.476842 0.031 Uiso 0.930(3) 1 calc R U P A 1
C1 C -0.0068(8) 0.2580(15) 0.2592(7) 0.0235(15) Uani 0.930(3) 1 d D . P A 1
H1A H -0.013175 0.082676 0.214920 0.028 Uiso 0.930(3) 1 calc R U P A 1
H1B H -0.109961 0.279202 0.276120 0.028 Uiso 0.930(3) 1 calc R U P A 1
C2 C 0.1609(8) 0.5300(17) 0.1801(6) 0.0177(15) Uani 0.930(3) 1 d D . P A 1
C3 C 0.1685(9) 0.7202(15) 0.0941(6) 0.0243(15) Uani 0.930(3) 1 d D . P A 1
H3 H 0.070360 0.797759 0.039525 0.029 Uiso 0.930(3) 1 calc R U P A 1
C4 C 0.3183(10) 0.7979(17) 0.0874(8) 0.0258(19) Uani 0.930(3) 1 d D . P A 1
H4 H 0.323818 0.928357 0.028701 0.031 Uiso 0.930(3) 1 calc R U P A 1
C5 C 0.4592(9) 0.6827(15) 0.1675(6) 0.0232(15) Uani 0.930(3) 1 d D . P A 1
C6 C 0.1344(8) 0.2437(14) 0.3780(6) 0.0192(14) Uani 0.930(3) 1 d D . P A 1
H6 H 0.117567 0.083946 0.426028 0.023 Uiso 0.930(3) 1 calc R U P A 1
C7 C 0.4553(9) 0.4897(13) 0.2533(6) 0.0174(14) Uani 0.930(3) 1 d D . P A 1
H7 H 0.553976 0.411802 0.306955 0.021 Uiso 0.930(3) 1 calc R U P A 1
C8 C 0.3040(8) 0.4110(12) 0.2600(6) 0.0138(12) Uani 0.930(3) 1 d D . P A 1
C9 C 0.2943(8) 0.2032(13) 0.3538(6) 0.0152(13) Uani 0.930(3) 1 d D . P A 1
H9 H 0.290355 0.016383 0.317340 0.018 Uiso 0.930(3) 1 calc R U P A 1
C8A C 0.411(5) 0.398(15) 0.246(6) 0.0138(12) Uani 0.070(3) 1 d D . P A 2
Cl1A Cl 0.776(3) 0.776(6) 0.175(2) 0.0372(5) Uani 0.070(3) 1 d D . P A 2
C5A C 0.580(4) 0.668(15) 0.166(6) 0.0232(15) Uani 0.070(3) 1 d D . P A 2
C4A C 0.446(5) 0.804(16) 0.087(7) 0.0258(19) Uani 0.070(3) 1 d D . P A 2
H4A H 0.459715 0.946856 0.036342 0.031 Uiso 0.070(3) 1 calc R U P A 2
C7A C 0.567(5) 0.475(13) 0.249(6) 0.0174(14) Uani 0.070(3) 1 d D . P A 2
H7A H 0.662078 0.397434 0.307780 0.021 Uiso 0.070(3) 1 calc R U P A 2
C3A C 0.291(6) 0.73(3) 0.084(11) 0.0243(15) Uani 0.070(3) 1 d D . P A 2
H3A H 0.197123 0.812973 0.028122 0.029 Uiso 0.070(3) 1 calc R U P A 2
C2A C 0.275(5) 0.531(15) 0.164(6) 0.0177(15) Uani 0.070(3) 1 d D . P A 2
C9A C 0.386(5) 0.199(10) 0.338(4) 0.0152(13) Uani 0.070(3) 1 d D . P A 2
H9A H 0.381270 0.010395 0.302253 0.018 Uiso 0.070(3) 1 calc R U P A 2
O1A O 0.117(5) 0.495(17) 0.163(7) 0.0223(11) Uani 0.070(3) 1 d D . P A 2
O2A O 0.515(6) 0.198(14) 0.449(4) 0.0206(10) Uani 0.070(3) 1 d D . P A 2
H2A H 0.558845 0.051153 0.463732 0.031 Uiso 0.070(3) 1 d R U P A 2
C6A C 0.221(5) 0.248(9) 0.354(4) 0.0192(14) Uani 0.070(3) 1 d D . P A 2
H6A H 0.196219 0.092218 0.399893 0.023 Uiso 0.070(3) 1 calc R U P A 2
C1A C 0.090(6) 0.266(12) 0.229(4) 0.0235(15) Uani 0.070(3) 1 d D . P A 2
H1AA H 0.091020 0.095103 0.182904 0.028 Uiso 0.070(3) 1 calc R U P A 2
H1AB H -0.018657 0.282291 0.237169 0.028 Uiso 0.070(3) 1 calc R U P A 2
Cl2A Cl 0.228(3) 0.566(5) 0.4347(18) 0.0219(4) Uani 0.070(3) 1 d D . P A 2


_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 C5 1.750(7) . ?
Cl2 C6 1.803(7) . ?
O1 C1 1.421(9) . ?
O1 C2 1.378(8) . ?
O2 H2 0.8400 . ?
O2 C9 1.401(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C6 1.506(10) . ?
C2 C3 1.386(10) . ?
C2 C8 1.398(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(12) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(11) . ?
C5 C7 1.386(10) . ?
C6 H6 1.0000 . ?
C6 C9 1.527(9) . ?
C7 H7 0.9500 . ?
C7 C8 1.399(10) . ?
C8 C9 1.517(9) . ?
C9 H9 1.0000 . ?
C8A C7A 1.40(3) . ?
C8A C2A 1.40(3) . ?
C8A C9A 1.51(3) . ?
Cl1A C5A 1.75(3) . ?
C5A C4A 1.38(3) . ?
C5A C7A 1.39(3) . ?
C4A H4A 0.9500 . ?
C4A C3A 1.38(3) . ?
C7A H7A 0.9500 . ?
C3A H3A 0.9500 . ?
C3A C2A 1.38(3) . ?
C2A O1A 1.38(3) . ?
C9A H9A 1.0000 . ?
C9A O2A 1.39(3) . ?
C9A C6A 1.53(3) . ?
O1A C1A 1.42(3) . ?
O2A H2A 0.7990 . ?
C6A H6A 1.0000 . ?
C6A C1A 1.51(3) . ?
C6A Cl2A 1.81(3) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?

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 O1 C1 116.7(5) . . ?
C9 O2 H2 109.5 . . ?
O1 C1 H1A 108.9 . . ?
O1 C1 H1B 108.9 . . ?
O1 C1 C6 113.2(5) . . ?
H1A C1 H1B 107.8 . . ?
C6 C1 H1A 108.9 . . ?
C6 C1 H1B 108.9 . . ?
O1 C2 C3 115.8(6) . . ?
O1 C2 C8 123.6(6) . . ?
C3 C2 C8 120.5(6) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(7) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.9(7) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 Cl1 119.9(6) . . ?
C4 C5 C7 122.0(7) . . ?
C7 C5 Cl1 118.2(6) . . ?
Cl2 C6 H6 109.0 . . ?
C1 C6 Cl2 110.1(5) . . ?
C1 C6 H6 109.0 . . ?
C1 C6 C9 109.7(5) . . ?
C9 C6 Cl2 110.0(4) . . ?
C9 C6 H6 109.0 . . ?
C5 C7 H7 120.4 . . ?
C5 C7 C8 119.2(6) . . ?
C8 C7 H7 120.4 . . ?
C2 C8 C7 119.1(6) . . ?
C2 C8 C9 120.1(6) . . ?
C7 C8 C9 120.8(6) . . ?
O2 C9 C6 112.8(5) . . ?
O2 C9 C8 112.3(5) . . ?
O2 C9 H9 107.3 . . ?
C6 C9 H9 107.3 . . ?
C8 C9 C6 109.4(5) . . ?
C8 C9 H9 107.3 . . ?
C7A C8A C9A 122(3) . . ?
C2A C8A C7A 119(3) . . ?
C2A C8A C9A 119(3) . . ?
C4A C5A Cl1A 118(3) . . ?
C4A C5A C7A 122(3) . . ?
C7A C5A Cl1A 119(3) . . ?
C5A C4A H4A 120.7 . . ?
C5A C4A C3A 119(3) . . ?
C3A C4A H4A 120.7 . . ?
C8A C7A H7A 120.7 . . ?
C5A C7A C8A 119(3) . . ?
C5A C7A H7A 120.7 . . ?
C4A C3A H3A 120.1 . . ?
C2A C3A C4A 120(3) . . ?
C2A C3A H3A 120.1 . . ?
C3A C2A C8A 122(3) . . ?
O1A C2A C8A 123(3) . . ?
O1A C2A C3A 115(3) . . ?
C8A C9A H9A 106.8 . . ?
C8A C9A C6A 111(3) . . ?
O2A C9A C8A 113(3) . . ?
O2A C9A H9A 106.8 . . ?
O2A C9A C6A 112(3) . . ?
C6A C9A H9A 106.8 . . ?
C2A O1A C1A 116(4) . . ?
C9A O2A H2A 112.1 . . ?
C9A C6A H6A 109.7 . . ?
C9A C6A Cl2A 110(3) . . ?
C1A C6A C9A 108(3) . . ?
C1A C6A H6A 109.7 . . ?
C1A C6A Cl2A 110(3) . . ?
Cl2A C6A H6A 109.7 . . ?
O1A C1A C6A 111(3) . . ?
O1A C1A H1AA 109.4 . . ?
O1A C1A H1AB 109.4 . . ?
C6A C1A H1AA 109.4 . . ?
C6A C1A H1AB 109.4 . . ?
H1AA C1A H1AB 108.0 . . ?

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
Cl1 C5 C7 C8 178.6(5) . . . . ?
Cl2 C6 C9 O2 53.6(6) . . . . ?
Cl2 C6 C9 C8 -72.1(6) . . . . ?
O1 C1 C6 Cl2 61.1(7) . . . . ?
O1 C1 C6 C9 -60.2(7) . . . . ?
O1 C2 C3 C4 176.5(7) . . . . ?
O1 C2 C8 C7 -176.2(6) . . . . ?
O1 C2 C8 C9 2.8(10) . . . . ?
C1 O1 C2 C3 171.7(6) . . . . ?
C1 O1 C2 C8 -11.0(10) . . . . ?
C1 C6 C9 O2 174.9(5) . . . . ?
C1 C6 C9 C8 49.1(7) . . . . ?
C2 O1 C1 C6 39.9(8) . . . . ?
C2 C3 C4 C5 0.1(12) . . . . ?
C2 C8 C9 O2 -148.8(6) . . . . ?
C2 C8 C9 C6 -22.8(8) . . . . ?
C3 C2 C8 C7 0.9(10) . . . . ?
C3 C2 C8 C9 179.9(6) . . . . ?
C3 C4 C5 Cl1 -178.5(6) . . . . ?
C3 C4 C5 C7 0.7(12) . . . . ?
C4 C5 C7 C8 -0.7(10) . . . . ?
C5 C7 C8 C2 -0.2(9) . . . . ?
C5 C7 C8 C9 -179.2(6) . . . . ?
C7 C8 C9 O2 30.2(8) . . . . ?
C7 C8 C9 C6 156.2(6) . . . . ?
C8 C2 C3 C4 -0.9(12) . . . . ?
C8A C2A O1A C1A -15(13) . . . . ?
C8A C9A C6A C1A 48(5) . . . . ?
C8A C9A C6A Cl2A -71(5) . . . . ?
Cl1A C5A C4A C3A -177(10) . . . . ?
Cl1A C5A C7A C8A 177(7) . . . . ?
C5A C4A C3A C2A 3(20) . . . . ?
C4A C5A C7A C8A 6(14) . . . . ?
C4A C3A C2A C8A -2(20) . . . . ?
C4A C3A C2A O1A 173(12) . . . . ?
C7A C8A C2A C3A 2(15) . . . . ?
C7A C8A C2A O1A -172(8) . . . . ?
C7A C8A C9A O2A 27(9) . . . . ?
C7A C8A C9A C6A 154(7) . . . . ?
C7A C5A C4A C3A -6(16) . . . . ?
C3A C2A O1A C1A 170(10) . . . . ?
C2A C8A C7A C5A -4(13) . . . . ?
C2A C8A C9A O2A -146(7) . . . . ?
C2A C8A C9A C6A -20(9) . . . . ?
C2A O1A C1A C6A 47(9) . . . . ?
C9A C8A C7A C5A -177(7) . . . . ?
C9A C8A C2A C3A 175(10) . . . . ?
C9A C8A C2A O1A 2(13) . . . . ?
C9A C6A C1A O1A -64(5) . . . . ?
O2A C9A C6A C1A 176(4) . . . . ?
O2A C9A C6A Cl2A 56(5) . . . . ?
Cl2A C6A C1A O1A 56(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
