# 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_cu_aa_114bs_matousova
_database_code_depnum_ccdc_archive 'CCDC 1985309'
loop_
_audit_author_name
_audit_author_address
'Ivana Cisarova'
;Charles Univerzity
Czech Republic
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2021-03-18 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         'C17 H15 Cl3 O3'
_chemical_formula_sum            'C17 H15 Cl3 O3'
_chemical_formula_weight         373.64
_chemical_compound_source        'synthesized by the authors'

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   21.5473(6)
_cell_length_b                   6.9275(2)
_cell_length_c                   10.8993(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1626.93(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9616
_cell_measurement_theta_min      4.5463
_cell_measurement_theta_max      72.1208

_exptl_crystal_description       bar
_exptl_crystal_colour            orange-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.151
_exptl_absorpt_coefficient_mu    5.205
_shelx_estimated_absorpt_T_min   0.237
_shelx_estimated_absorpt_T_max   0.507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.32
_exptl_absorpt_correction_T_max  0.51
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON III'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26286
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.546
_diffrn_reflns_theta_max         72.267
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1738
_reflns_number_gt                1696
_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 Instrument Service vV6.2.12'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_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)+(0.0458P)²+1.4029P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         1738
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1255
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_restrained_S_all      1.165
_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 0.61918(14) 0.250000 0.7125(3) 0.0428(7) Uani 1 2 d S T P . .
H1A H 0.639799 0.365290 0.677540 0.051 Uiso 0.5 1 d R U P . .
H1B H 0.639799 0.134710 0.677540 0.051 Uiso 0.5 1 d R U P . .
O1 O 0.46278(12) 0.2094(6) 0.9501(2) 0.0425(15) Uani 0.5 1 d . . P . .
C2 C 0.62830(19) 0.2840(14) 0.8514(3) 0.044(3) Uani 0.5 1 d . . P . .
H2A H 0.669482 0.233709 0.875948 0.053 Uiso 0.5 1 d R U P . .
H2B H 0.627571 0.424362 0.868274 0.053 Uiso 0.5 1 d R U P . .
O2 O 0.58445(15) 0.250000 0.2308(2) 0.0685(8) Uani 1 2 d S T P . .
C3 C 0.57811(19) 0.1846(7) 0.9288(3) 0.0431(11) Uani 0.5 1 d . . P . .
H3A H 0.571189 0.064899 0.917442 0.052 Uiso 0.5 1 d R U P . .
H3B H 0.591591 0.214500 1.015334 0.052 Uiso 0.5 1 d R U P . .
O3 O 0.62971(11) 0.250000 0.4579(2) 0.0552(7) Uani 1 2 d S T P . .
C4 C 0.51874(18) 0.2894(6) 0.8976(3) 0.0360(16) Uani 0.5 1 d . . P . .
H4 H 0.522310 0.430876 0.914505 0.043 Uiso 0.5 1 d R U P . .
C5 C 0.41313(15) 0.250000 0.8648(3) 0.0448(8) Uani 1 2 d S T P . .
H5A H 0.386851 0.366214 0.874637 0.054 Uiso 0.5 1 d R U P . .
H5B H 0.386851 0.133786 0.874637 0.054 Uiso 0.5 1 d R U P . .
C6 C 0.44441(13) 0.250000 0.7410(3) 0.0328(6) Uani 1 2 d S T P . .
C7 C 0.42124(14) 0.250000 0.6222(3) 0.0349(6) Uani 1 2 d S T P . .
C8 C 0.46481(14) 0.250000 0.5260(2) 0.0317(6) Uani 1 2 d S T P . .
C9 C 0.44348(16) 0.250000 0.3987(3) 0.0413(7) Uani 1 2 d S T P . .
H9 H 0.399976 0.250000 0.384553 0.050 Uiso 1 2 calc R U P . .
C10 C 0.48107(18) 0.250000 0.2999(3) 0.0469(8) Uani 1 2 d S T P . .
H10 H 0.463642 0.250000 0.219864 0.056 Uiso 1 2 calc R U P . .
C11 C 0.54741(18) 0.250000 0.3148(3) 0.0441(8) Uani 1 2 d S T P . .
C12 C 0.57368(15) 0.250000 0.4467(3) 0.0378(7) Uani 1 2 d S T P . .
C13 C 0.52993(13) 0.250000 0.5506(2) 0.0311(6) Uani 1 2 d S T P . .
C14 C 0.55186(14) 0.250000 0.6721(2) 0.0349(6) Uani 1 2 d S T P . .
C15 C 0.50703(14) 0.250000 0.7629(3) 0.0421(7) Uani 1 2 d S T P . .
C16 C 0.35197(15) 0.250000 0.6014(3) 0.0522(9) Uani 1 2 d S T P . .
H16A H 0.330647 0.225421 0.679244 0.078 Uiso 0.5 1 calc R U P . .
H16B H 0.341182 0.148762 0.542309 0.078 Uiso 0.5 1 calc R U P . .
H16C H 0.339124 0.375817 0.569060 0.078 Uiso 0.5 1 calc R U P . .
C1S C 0.73121(17) 0.250000 0.2351(4) 0.0571(10) Uani 1 2 d S T P . .
H1S H 0.689781 0.250000 0.276488 0.068 Uiso 1 2 d R U P . .
Cl1S Cl 0.79010(8) 0.250000 0.34738(12) 0.1024(5) Uani 1 2 d S T P . .
Cl2S Cl 0.73746(3) 0.45682(12) 0.14263(7) 0.0664(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 C14 1.516(4) . ?
C1 C2 1.544(5) 7_565 ?
C1 C2 1.544(5) . ?
C1 H1A 0.9901 . ?
C1 H1B 0.9901 . ?
O1 O1 0.562(9) 7_565 ?
O1 C4 1.334(4) 7_565 ?
O1 C4 1.445(5) . ?
O1 C5 1.445(4) . ?
C2 C2 0.471(19) 7_565 ?
C2 C3 1.389(6) 7_565 ?
C2 C3 1.535(7) . ?
C2 H2A 0.9901 . ?
C2 H2B 0.9901 . ?
C2 H2A 0.935(3) 7_565 ?
O2 C11 1.215(4) . ?
C3 C3 0.906(9) 7_565 ?
C3 C4 1.336(6) 7_565 ?
C3 C4 1.510(6) . ?
C3 H3A 0.8518 . ?
C3 H3B 1.0084 . ?
O3 C12 1.214(4) . ?
C4 C4 0.546(9) 7_565 ?
C4 C15 1.515(4) . ?
C4 H4 1.0000 . ?
C5 C6 1.508(4) . ?
C5 H5A 0.9901 . ?
C5 H5B 0.9901 . ?
C6 C15 1.370(4) . ?
C6 C7 1.388(4) . ?
C7 C8 1.407(4) . ?
C7 C16 1.510(4) . ?
C8 C13 1.429(4) . ?
C8 C9 1.462(4) . ?
C9 C10 1.347(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.439(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.545(4) . ?
C12 C13 1.473(4) . ?
C13 C14 1.406(4) . ?
C14 C15 1.383(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 H16A 0.980(18) 7_565 ?
C16 H16B 0.98(5) 7_565 ?
C16 H16C 0.98(3) 7_565 ?
C1S Cl2S 1.757(2) . ?
C1S Cl2S 1.757(2) 7_565 ?
C1S Cl1S 1.763(4) . ?
C1S H1S 1.0001 . ?

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
C14 C1 C2 114.0(3) . 7_565 ?
C14 C1 C2 114.0(3) . . ?
C2 C1 C2 17.5(7) 7_565 . ?
C14 C1 H1A 108.5 . . ?
C2 C1 H1A 116.3 7_565 . ?
C2 C1 H1A 101.4 . . ?
C14 C1 H1B 108.5 . . ?
C2 C1 H1B 101.4 7_565 . ?
C2 C1 H1B 116.3 . . ?
H1A C1 H1B 107.5 . . ?
O1 O1 C4 89.7(3) 7_565 7_565 ?
O1 O1 C4 67.5(2) 7_565 . ?
C4 O1 C4 22.2(4) 7_565 . ?
O1 O1 C5 78.79(17) 7_565 . ?
C4 O1 C5 113.1(3) 7_565 . ?
C4 O1 C5 106.8(3) . . ?
C2 C2 C3 99.0(4) 7_565 7_565 ?
C2 C2 C3 63.4(4) 7_565 . ?
C3 C2 C3 35.6(4) 7_565 . ?
C2 C2 C1 81.2(4) 7_565 . ?
C3 C2 C1 121.4(3) 7_565 . ?
C3 C2 C1 112.4(4) . . ?
C2 C2 H2A 69.4 7_565 . ?
C3 C2 H2A 126.0 7_565 . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C2 C2 H2B 169.2 7_565 . ?
C3 C2 H2B 73.8 7_565 . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C2 C2 H2A 82.5(12) 7_565 7_565 ?
C3 C2 H2A 125.8(2) 7_565 7_565 ?
C3 C2 H2A 116.9(8) . 7_565 ?
C1 C2 H2A 112.4(4) . 7_565 ?
H2A C2 H2A 13.1 . 7_565 ?
H2B C2 H2A 95.2 . 7_565 ?
C3 C3 C4 82.3(3) 7_565 7_565 ?
C3 C3 C2 81.0(4) 7_565 7_565 ?
C4 C3 C2 124.8(4) 7_565 7_565 ?
C3 C3 C4 61.3(2) 7_565 . ?
C4 C3 C4 21.0(3) 7_565 . ?
C2 C3 C4 116.6(4) 7_565 . ?
C3 C3 C2 63.4(4) 7_565 . ?
C4 C3 C2 118.3(4) 7_565 . ?
C2 C3 C2 17.6(7) 7_565 . ?
C4 C3 C2 104.9(4) . . ?
C3 C3 H3A 166.9 7_565 . ?
C4 C3 H3A 85.8 7_565 . ?
C2 C3 H3A 101.6 7_565 . ?
C4 C3 H3A 106.7 . . ?
C2 C3 H3A 118.7 . . ?
C3 C3 H3B 78.2 7_565 . ?
C4 C3 H3B 119.1 7_565 . ?
C2 C3 H3B 108.2 7_565 . ?
C4 C3 H3B 110.9 . . ?
C2 C3 H3B 102.7 . . ?
H3A C3 H3B 112.7 . . ?
C4 C4 O1 90.3(3) 7_565 7_565 ?
C4 C4 C3 97.7(3) 7_565 7_565 ?
O1 C4 C3 139.1(3) 7_565 7_565 ?
C4 C4 O1 67.4(2) 7_565 . ?
O1 C4 O1 22.9(4) 7_565 . ?
C3 C4 O1 138.6(3) 7_565 . ?
C4 C4 C3 61.3(2) 7_565 . ?
O1 C4 C3 132.2(4) 7_565 . ?
C3 C4 C3 36.5(4) 7_565 . ?
O1 C4 C3 115.7(4) . . ?
C4 C4 C15 79.61(17) 7_565 . ?
O1 C4 C15 105.4(3) 7_565 . ?
C3 C4 C15 115.5(3) 7_565 . ?
O1 C4 C15 100.1(3) . . ?
C3 C4 C15 105.8(3) . . ?
C4 C4 H4 168.5 7_565 . ?
O1 C4 H4 89.1 7_565 . ?
C3 C4 H4 75.4 7_565 . ?
O1 C4 H4 111.5 . . ?
C3 C4 H4 111.4 . . ?
C15 C4 H4 111.6 . . ?
O1 C5 O1 22.4(3) . 7_565 ?
O1 C5 C6 104.2(2) . . ?
O1 C5 C6 104.2(2) 7_565 . ?
O1 C5 H5A 120.8 . . ?
O1 C5 H5A 101.3 7_565 . ?
C6 C5 H5A 110.7 . . ?
O1 C5 H5B 101.3 . . ?
O1 C5 H5B 120.8 7_565 . ?
C6 C5 H5B 110.7 . . ?
H5A C5 H5B 108.8 . . ?
C15 C6 C7 121.1(3) . . ?
C15 C6 C5 106.5(2) . . ?
C7 C6 C5 132.4(3) . . ?
C6 C7 C8 117.1(3) . . ?
C6 C7 C16 119.7(3) . . ?
C8 C7 C16 123.2(3) . . ?
C7 C8 C13 121.0(2) . . ?
C7 C8 C9 119.8(3) . . ?
C13 C8 C9 119.1(3) . . ?
C10 C9 C8 124.7(3) . . ?
C10 C9 H9 117.6 . . ?
C8 C9 H9 117.6 . . ?
C9 C10 C11 120.5(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
O2 C11 C10 124.6(3) . . ?
O2 C11 C12 117.5(3) . . ?
C10 C11 C12 118.0(3) . . ?
O3 C12 C13 124.0(3) . . ?
O3 C12 C11 117.3(3) . . ?
C13 C12 C11 118.7(3) . . ?
C14 C13 C8 120.5(2) . . ?
C14 C13 C12 120.6(3) . . ?
C8 C13 C12 119.0(2) . . ?
C15 C14 C13 116.1(3) . . ?
C15 C14 C1 117.4(3) . . ?
C13 C14 C1 126.5(3) . . ?
C6 C15 C14 124.3(3) . . ?
C6 C15 C4 109.4(3) . . ?
C14 C15 C4 125.3(3) . . ?
C6 C15 C4 109.4(3) . 7_565 ?
C14 C15 C4 125.3(3) . 7_565 ?
C4 C15 C4 20.8(3) . 7_565 ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 C16 H16A 109.5(4) . 7_565 ?
H16A C16 H16A 20.0 . 7_565 ?
H16B C16 H16A 125.6 . 7_565 ?
H16C C16 H16A 91.4 . 7_565 ?
C7 C16 H16B 109.5(10) . 7_565 ?
H16A C16 H16B 125.6 . 7_565 ?
H16B C16 H16B 91.4 . 7_565 ?
H16C C16 H16B 20.0 . 7_565 ?
H16A C16 H16B 109.5 7_565 7_565 ?
C7 C16 H16C 109.5(6) . 7_565 ?
H16A C16 H16C 91.4 . 7_565 ?
H16B C16 H16C 20.0 . 7_565 ?
H16C C16 H16C 125.6 . 7_565 ?
H16A C16 H16C 109.5 7_565 7_565 ?
H16B C16 H16C 109.5 7_565 7_565 ?
Cl2S C1S Cl2S 109.3(2) . 7_565 ?
Cl2S C1S Cl1S 110.06(14) . . ?
Cl2S C1S Cl1S 110.06(14) 7_565 . ?
Cl2S C1S H1S 109.1 . . ?
Cl2S C1S H1S 109.1 7_565 . ?
Cl1S C1S H1S 109.2 . . ?

_refine_diff_density_max         0.372
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.050

