# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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 2216510'
loop_
_audit_author_name
_audit_author_address
'Duyi Shen'
;Qufu Normal University
China
;
_audit_update_record             
;
2022-10-31 deposited with the CCDC.	2023-04-20 downloaded from the CCDC.
;
_audit_creation_date             2022-03-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H10 Cl2 O3'
_chemical_formula_sum            'C16 H10 Cl2 O3'
_chemical_formula_weight         321.14
_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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.1797(6)
_cell_length_b                   9.7742(5)
_cell_length_c                   12.8956(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.249(2)
_cell_angle_gamma                90
_cell_volume                     1400.76(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7376
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.883
_cell_measurement_theta_min      2.291
_shelx_estimated_absorpt_T_max   0.916
_shelx_estimated_absorpt_T_min   0.900
_exptl_absorpt_coefficient_mu    0.469
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0594 before and 0.0491 after correction.
The Ratio of minimum to maximum transmission is 0.9128.
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    1.523
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20016
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.310
_diffrn_reflns_theta_min         2.621
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2298
_reflns_number_total             3462
_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       ?
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3462
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.016
_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)+(0.0455P)²+0.4365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1113
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C11(H11), C13(H13), C15(H15), C16(H16)
;
_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 0.68885(6) 0.78452(7) 0.73249(5) 0.0822(2) Uani 1 1 d . . . . .
Cl2 Cl -0.09712(6) 0.74436(8) -0.04667(5) 0.0883(2) Uani 1 1 d . . . . .
O1 O 0.35698(11) 0.63648(13) 0.28630(9) 0.0512(3) Uani 1 1 d . . . . .
O2 O 0.22372(12) 0.90555(14) 0.40656(10) 0.0610(4) Uani 1 1 d . . . . .
O3 O 0.24612(12) 0.58917(14) 0.42668(10) 0.0575(4) Uani 1 1 d . . . . .
C1 C 0.41309(16) 0.64239(17) 0.54311(13) 0.0443(4) Uani 1 1 d . . . . .
C2 C 0.26534(17) 0.5855(2) 0.20985(15) 0.0545(5) Uani 1 1 d . . . . .
H2A H 0.233267 0.501321 0.235457 0.065 Uiso 1 1 calc R U . . .
H2B H 0.301184 0.564081 0.146606 0.065 Uiso 1 1 calc R U . . .
C3 C 0.58408(17) 0.75686(19) 0.62412(15) 0.0531(5) Uani 1 1 d . . . . .
C4 C 0.22754(15) 0.80831(18) 0.34786(14) 0.0452(4) Uani 1 1 d . . . . .
C5 C 0.59093(17) 0.8371(2) 0.53682(16) 0.0556(5) Uani 1 1 d . . . . .
H5 H 0.651950 0.901590 0.535638 0.067 Uiso 1 1 calc R U . . .
C6 C 0.41727(15) 0.72338(17) 0.45613(13) 0.0444(4) Uani 1 1 d . . . . .
C7 C -0.00257(17) 0.7634(2) 0.06846(15) 0.0572(5) Uani 1 1 d . . . . .
C8 C 0.30811(16) 0.54783(19) 0.52554(14) 0.0496(4) Uani 1 1 d . . . . .
H8A H 0.334695 0.453551 0.522893 0.059 Uiso 1 1 calc R U . . .
H8B H 0.256227 0.556966 0.580733 0.059 Uiso 1 1 calc R U . . .
C9 C 0.50644(17) 0.8209(2) 0.45132(15) 0.0543(5) Uani 1 1 d . . . . .
H9 H 0.509327 0.874141 0.391882 0.065 Uiso 1 1 calc R U . . .
C10 C 0.14920(15) 0.79524(18) 0.24919(14) 0.0452(4) Uani 1 1 d . . . . .
C11 C 0.08587(16) 0.6676(2) 0.09330(14) 0.0514(4) Uani 1 1 d . . . . .
H11 H 0.093425 0.592697 0.050065 0.062 Uiso 1 1 calc R U . . .
C12 C 0.31338(15) 0.68897(18) 0.37704(13) 0.0453(4) Uani 1 1 d . . . . .
C13 C 0.05919(17) 0.8911(2) 0.22167(16) 0.0577(5) Uani 1 1 d . . . . .
H13 H 0.050152 0.965635 0.264943 0.069 Uiso 1 1 calc R U . . .
C14 C 0.16402(16) 0.68436(18) 0.18405(14) 0.0451(4) Uani 1 1 d . . . . .
C15 C -0.01653(18) 0.8761(2) 0.13078(17) 0.0656(6) Uani 1 1 d . . . . .
H15 H -0.075965 0.940697 0.111648 0.079 Uiso 1 1 calc R U . . .
C16 C 0.49759(17) 0.65697(19) 0.62906(14) 0.0513(4) Uani 1 1 d . . . . .
H16 H 0.496190 0.601831 0.687690 0.062 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 C3 1.7440(18) . ?
Cl2 C7 1.7362(19) . ?
O1 C2 1.432(2) . ?
O1 C12 1.412(2) . ?
O2 C4 1.219(2) . ?
O3 C8 1.441(2) . ?
O3 C12 1.425(2) . ?
C1 C6 1.378(2) . ?
C1 C8 1.492(2) . ?
C1 C16 1.383(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C14 1.498(2) . ?
C3 C5 1.381(3) . ?
C3 C16 1.380(3) . ?
C4 C10 1.470(2) . ?
C4 C12 1.531(3) . ?
C5 H5 0.9300 . ?
C5 C9 1.381(3) . ?
C6 C9 1.385(2) . ?
C6 C12 1.498(2) . ?
C7 C11 1.373(3) . ?
C7 C15 1.383(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9 0.9300 . ?
C10 C13 1.392(2) . ?
C10 C14 1.392(2) . ?
C11 H11 0.9300 . ?
C11 C14 1.392(2) . ?
C13 H13 0.9300 . ?
C13 C15 1.377(3) . ?
C15 H15 0.9300 . ?
C16 H16 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
C12 O1 C2 114.29(13) . . ?
C12 O3 C8 111.27(13) . . ?
C6 C1 C8 109.16(15) . . ?
C6 C1 C16 120.82(17) . . ?
C16 C1 C8 130.02(17) . . ?
O1 C2 H2A 108.9 . . ?
O1 C2 H2B 108.9 . . ?
O1 C2 C14 113.31(15) . . ?
H2A C2 H2B 107.7 . . ?
C14 C2 H2A 108.9 . . ?
C14 C2 H2B 108.9 . . ?
C5 C3 Cl1 118.24(15) . . ?
C16 C3 Cl1 119.04(15) . . ?
C16 C3 C5 122.73(17) . . ?
O2 C4 C10 123.21(17) . . ?
O2 C4 C12 120.33(16) . . ?
C10 C4 C12 116.43(15) . . ?
C3 C5 H5 120.3 . . ?
C9 C5 C3 119.46(18) . . ?
C9 C5 H5 120.3 . . ?
C1 C6 C9 121.34(16) . . ?
C1 C6 C12 109.43(15) . . ?
C9 C6 C12 129.22(16) . . ?
C11 C7 Cl2 118.84(16) . . ?
C11 C7 C15 122.09(18) . . ?
C15 C7 Cl2 119.04(15) . . ?
O3 C8 C1 104.79(14) . . ?
O3 C8 H8A 110.8 . . ?
O3 C8 H8B 110.8 . . ?
C1 C8 H8A 110.8 . . ?
C1 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
C5 C9 C6 118.45(18) . . ?
C5 C9 H9 120.8 . . ?
C6 C9 H9 120.8 . . ?
C13 C10 C4 120.55(17) . . ?
C14 C10 C4 119.42(16) . . ?
C14 C10 C13 120.01(17) . . ?
C7 C11 H11 120.5 . . ?
C7 C11 C14 119.09(18) . . ?
C14 C11 H11 120.5 . . ?
O1 C12 O3 111.72(14) . . ?
O1 C12 C4 109.68(14) . . ?
O1 C12 C6 109.50(14) . . ?
O3 C12 C4 106.53(14) . . ?
O3 C12 C6 104.81(14) . . ?
C6 C12 C4 114.52(15) . . ?
C10 C13 H13 119.8 . . ?
C15 C13 C10 120.40(18) . . ?
C15 C13 H13 119.8 . . ?
C10 C14 C2 120.31(16) . . ?
C11 C14 C2 120.09(16) . . ?
C11 C14 C10 119.58(16) . . ?
C7 C15 H15 120.6 . . ?
C13 C15 C7 118.78(18) . . ?
C13 C15 H15 120.6 . . ?
C1 C16 H16 121.4 . . ?
C3 C16 C1 117.17(17) . . ?
C3 C16 H16 121.4 . . ?

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
Cl1 C3 C5 C9 -177.62(16) . . . . ?
Cl1 C3 C16 C1 177.27(14) . . . . ?
Cl2 C7 C11 C14 178.25(15) . . . . ?
Cl2 C7 C15 C13 -179.61(17) . . . . ?
O1 C2 C14 C10 -15.8(3) . . . . ?
O1 C2 C14 C11 162.58(16) . . . . ?
O2 C4 C10 C13 -4.8(3) . . . . ?
O2 C4 C10 C14 176.52(17) . . . . ?
O2 C4 C12 O1 -145.10(16) . . . . ?
O2 C4 C12 O3 93.83(19) . . . . ?
O2 C4 C12 C6 -21.5(2) . . . . ?
C1 C6 C9 C5 -1.0(3) . . . . ?
C1 C6 C12 O1 -116.75(16) . . . . ?
C1 C6 C12 O3 3.23(19) . . . . ?
C1 C6 C12 C4 119.59(16) . . . . ?
C2 O1 C12 O3 57.58(18) . . . . ?
C2 O1 C12 C4 -60.30(18) . . . . ?
C2 O1 C12 C6 173.24(14) . . . . ?
C3 C5 C9 C6 -0.2(3) . . . . ?
C4 C10 C13 C15 -177.91(19) . . . . ?
C4 C10 C14 C2 -5.0(3) . . . . ?
C4 C10 C14 C11 176.56(16) . . . . ?
C5 C3 C16 C1 -2.3(3) . . . . ?
C6 C1 C8 O3 -5.3(2) . . . . ?
C6 C1 C16 C3 1.0(3) . . . . ?
C7 C11 C14 C2 -176.68(18) . . . . ?
C7 C11 C14 C10 1.7(3) . . . . ?
C8 O3 C12 O1 111.75(16) . . . . ?
C8 O3 C12 C4 -128.49(15) . . . . ?
C8 O3 C12 C6 -6.74(19) . . . . ?
C8 C1 C6 C9 -179.94(17) . . . . ?
C8 C1 C6 C12 1.3(2) . . . . ?
C8 C1 C16 C3 -178.34(18) . . . . ?
C9 C6 C12 O1 64.6(2) . . . . ?
C9 C6 C12 O3 -175.41(18) . . . . ?
C9 C6 C12 C4 -59.0(3) . . . . ?
C10 C4 C12 O1 37.2(2) . . . . ?
C10 C4 C12 O3 -83.92(17) . . . . ?
C10 C4 C12 C6 160.72(15) . . . . ?
C10 C13 C15 C7 1.0(3) . . . . ?
C11 C7 C15 C13 -1.4(3) . . . . ?
C12 O1 C2 C14 50.4(2) . . . . ?
C12 O3 C8 C1 7.49(19) . . . . ?
C12 C4 C10 C13 172.90(16) . . . . ?
C12 C4 C10 C14 -5.8(2) . . . . ?
C12 C6 C9 C5 177.49(18) . . . . ?
C13 C10 C14 C2 176.26(18) . . . . ?
C13 C10 C14 C11 -2.2(3) . . . . ?
C14 C10 C13 C15 0.8(3) . . . . ?
C15 C7 C11 C14 0.0(3) . . . . ?
C16 C1 C6 C9 0.6(3) . . . . ?
C16 C1 C6 C12 -178.15(16) . . . . ?
C16 C1 C8 O3 174.12(18) . . . . ?
C16 C3 C5 C9 1.9(3) . . . . ?

_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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2216611'
loop_
_audit_author_name
_audit_author_address
'Duyi Shen'
;Qufu Normal University
China
;
_audit_update_record             
;
2022-10-31 deposited with the CCDC.	2023-04-20 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         'C13 H13 Cl O3'
_chemical_formula_sum            'C13 H13 Cl O3'
_chemical_formula_weight         252.68

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'
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                   11.0050(13)
_cell_length_b                   8.3388(11)
_cell_length_c                   12.9789(18)
_cell_angle_alpha                90
_cell_angle_beta                 92.588(5)
_cell_angle_gamma                90
_cell_volume                     1189.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9795
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      28.29

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.314
_shelx_estimated_absorpt_T_min   0.7032
_shelx_estimated_absorpt_T_max   0.7457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15065
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.904
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.000
_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             2091
_reflns_number_gt                1876
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0414P)²+0.3435P] 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         2091
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0892
_refine_ls_wR_factor_gt          0.0864
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
C1 C 0.77757(14) 0.7418(2) 0.73588(12) 0.0484(4) Uani 1 1 d . . . . .
C2 C 0.78774(14) 0.8411(2) 0.65074(13) 0.0536(4) Uani 1 1 d . . . . .
H2 H 0.858253 0.900106 0.642059 0.064 Uiso 1 1 calc R U . . .
C3 C 0.69168(13) 0.85048(18) 0.57959(12) 0.0468(4) Uani 1 1 d . . . . .
H3 H 0.697115 0.916182 0.522083 0.056 Uiso 1 1 calc R U . . .
C4 C 0.58607(12) 0.76195(16) 0.59318(10) 0.0370(3) Uani 1 1 d . . . . .
C5 C 0.57720(12) 0.66322(16) 0.67934(10) 0.0362(3) Uani 1 1 d . . . . .
C6 C 0.67452(13) 0.65389(17) 0.75163(11) 0.0431(3) Uani 1 1 d . . . . .
H6 H 0.669765 0.589111 0.809634 0.052 Uiso 1 1 calc R U . . .
C7 C 0.46571(13) 0.56403(19) 0.69253(11) 0.0457(3) Uani 1 1 d . . . . .
H7A H 0.489914 0.458349 0.717022 0.055 Uiso 1 1 calc R U . . .
H7B H 0.417362 0.613054 0.744674 0.055 Uiso 1 1 calc R U . . .
C8 C 0.36384(13) 0.69442(16) 0.54921(10) 0.0372(3) Uani 1 1 d . . . . .
C9 C 0.48236(13) 0.77320(16) 0.51742(10) 0.0382(3) Uani 1 1 d . . . . .
C10 C 0.27787(14) 0.65730(19) 0.45799(11) 0.0497(4) Uani 1 1 d . . . . .
H10A H 0.312765 0.573651 0.416619 0.060 Uiso 1 1 calc R U . . .
H10B H 0.267821 0.752262 0.415294 0.060 Uiso 1 1 calc R U . . .
C11 C 0.15456(15) 0.6032(2) 0.49245(14) 0.0628(5) Uani 1 1 d . . . . .
H11A H 0.162195 0.499643 0.526222 0.075 Uiso 1 1 calc R U . . .
H11B H 0.098660 0.591898 0.432942 0.075 Uiso 1 1 calc R U . . .
C12 C 0.10536(16) 0.7255(3) 0.56656(17) 0.0687(5) Uani 1 1 d . . . . .
H12A H 0.088250 0.825330 0.530339 0.082 Uiso 1 1 calc R U . . .
H12B H 0.030013 0.686456 0.593374 0.082 Uiso 1 1 calc R U . . .
C13 C 0.19725(14) 0.7548(2) 0.65464(14) 0.0570(4) Uani 1 1 d . . . . .
H13A H 0.166526 0.836595 0.699826 0.068 Uiso 1 1 calc R U . . .
H13B H 0.208473 0.657041 0.694407 0.068 Uiso 1 1 calc R U . . .
Cl1 Cl 0.90078(4) 0.72509(8) 0.82439(4) 0.0796(2) Uani 1 1 d . . . . .
O1 O 0.39244(9) 0.54743(11) 0.59921(7) 0.0429(3) Uani 1 1 d . . . . .
O2 O 0.31283(8) 0.80570(12) 0.61758(7) 0.0425(3) Uani 1 1 d . . . . .
O3 O 0.48813(10) 0.83976(15) 0.43496(8) 0.0584(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 C6 1.373(2) . ?
C1 C2 1.389(2) . ?
C1 Cl1 1.7427(15) . ?
C2 C3 1.374(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.395(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.3956(18) . ?
C4 C9 1.475(2) . ?
C5 C6 1.3938(19) . ?
C5 C7 1.496(2) . ?
C6 H6 0.9300 . ?
C7 O1 1.4312(16) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.4157(16) . ?
C8 O2 1.4172(16) . ?
C8 C10 1.5137(19) . ?
C8 C9 1.534(2) . ?
C9 O3 1.2099(17) . ?
C10 C11 1.517(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.519(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.512(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O2 1.4438(18) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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
C6 C1 C2 122.23(14) . . ?
C6 C1 Cl1 118.83(12) . . ?
C2 C1 Cl1 118.94(12) . . ?
C3 C2 C1 118.77(14) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 120.34(14) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 120.16(13) . . ?
C3 C4 C9 120.40(12) . . ?
C5 C4 C9 119.44(12) . . ?
C6 C5 C4 119.53(13) . . ?
C6 C5 C7 120.09(12) . . ?
C4 C5 C7 120.35(12) . . ?
C1 C6 C5 118.98(13) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
O1 C7 C5 112.98(11) . . ?
O1 C7 H7A 109.0 . . ?
C5 C7 H7A 109.0 . . ?
O1 C7 H7B 109.0 . . ?
C5 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
O1 C8 O2 111.48(10) . . ?
O1 C8 C10 107.43(11) . . ?
O2 C8 C10 111.87(11) . . ?
O1 C8 C9 108.66(11) . . ?
O2 C8 C9 104.70(10) . . ?
C10 C8 C9 112.72(12) . . ?
O3 C9 C4 123.28(13) . . ?
O3 C9 C8 120.92(13) . . ?
C4 C9 C8 115.80(11) . . ?
C8 C10 C11 111.48(13) . . ?
C8 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C8 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C12 109.64(14) . . ?
C10 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C13 C12 C11 110.00(14) . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
O2 C13 C12 111.40(14) . . ?
O2 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
O2 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C8 O1 C7 114.16(10) . . ?
C8 O2 C13 113.33(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.5(2) . . . . ?
Cl1 C1 C2 C3 178.17(12) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C2 C3 C4 C9 179.35(13) . . . . ?
C3 C4 C5 C6 0.05(19) . . . . ?
C9 C4 C5 C6 -179.24(12) . . . . ?
C3 C4 C5 C7 -178.03(13) . . . . ?
C9 C4 C5 C7 2.68(19) . . . . ?
C2 C1 C6 C5 0.6(2) . . . . ?
Cl1 C1 C6 C5 -178.05(10) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C7 C5 C6 C1 177.70(13) . . . . ?
C6 C5 C7 O1 -161.42(12) . . . . ?
C4 C5 C7 O1 16.65(18) . . . . ?
C3 C4 C9 O3 10.2(2) . . . . ?
C5 C4 C9 O3 -170.53(13) . . . . ?
C3 C4 C9 C8 -169.79(12) . . . . ?
C5 C4 C9 C8 9.50(17) . . . . ?
O1 C8 C9 O3 139.58(13) . . . . ?
O2 C8 C9 O3 -101.20(14) . . . . ?
C10 C8 C9 O3 20.61(18) . . . . ?
O1 C8 C9 C4 -40.45(14) . . . . ?
O2 C8 C9 C4 78.76(13) . . . . ?
C10 C8 C9 C4 -159.42(12) . . . . ?
O1 C8 C10 C11 68.93(15) . . . . ?
O2 C8 C10 C11 -53.72(17) . . . . ?
C9 C8 C10 C11 -171.39(12) . . . . ?
C8 C10 C11 C12 52.98(19) . . . . ?
C10 C11 C12 C13 -54.3(2) . . . . ?
C11 C12 C13 O2 56.5(2) . . . . ?
O2 C8 O1 C7 -52.31(15) . . . . ?
C10 C8 O1 C7 -175.20(11) . . . . ?
C9 C8 O1 C7 62.57(14) . . . . ?
C5 C7 O1 C8 -51.37(16) . . . . ?
O1 C8 O2 C13 -64.26(15) . . . . ?
C10 C8 O2 C13 56.06(16) . . . . ?
C9 C8 O2 C13 178.43(12) . . . . ?
C12 C13 O2 C8 -57.96(18) . . . . ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.030

