# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2384541'
loop_
_audit_author_name
_audit_author_address
' Victor M. Deflon'
;Institute of Chemistry of Sao Carlos, University of Sao Paulo, Sao Carlos
Brazil
;
_audit_update_record             
;
2024-09-16 deposited with the CCDC.	2024-12-01 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            'C17 H15 Cl O3'
_chemical_formula_weight         302.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   10.8616(7)
_cell_length_b                   17.3612(11)
_cell_length_c                   8.0514(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1518.26(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4336
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      22.26

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.258
_shelx_estimated_absorpt_T_min   0.882
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4437
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            22340
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_av_R_equivalents  0.0863
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.212
_diffrn_reflns_theta_max         26.397
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3096
_reflns_number_gt                2274
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    1.000

_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    ?
_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)+(0.0298P)²+0.5240P] 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_abs_structure_details 
;
 Flack x determined using 802 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3096
_refine_ls_number_parameters     191
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1220
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 0.5404(4) 0.1197(2) 0.3288(6) 0.0575(11) Uani 1 1 d . . . . .
H1 H 0.620691 0.105368 0.354266 0.069 Uiso 1 1 calc R U . . .
C2 C 0.4664(4) 0.0688(3) 0.2429(6) 0.0598(11) Uani 1 1 d . . . . .
H2 H 0.496636 0.020923 0.210842 0.072 Uiso 1 1 calc R U . . .
C3 C 0.3478(4) 0.0895(2) 0.2053(5) 0.0544(11) Uani 1 1 d . . . . .
C4 C 0.3031(4) 0.1604(2) 0.2498(6) 0.0594(12) Uani 1 1 d . . . . .
H4 H 0.223356 0.174816 0.221179 0.071 Uiso 1 1 calc R U . . .
C5 C 0.3781(4) 0.2104(2) 0.3378(7) 0.0543(11) Uani 1 1 d . . . . .
H5 H 0.346938 0.257919 0.370820 0.065 Uiso 1 1 calc R U . . .
C6 C 0.4985(4) 0.1914(2) 0.3780(5) 0.0458(10) Uani 1 1 d . . . . .
C7 C 0.5801(4) 0.2440(2) 0.4818(5) 0.0459(10) Uani 1 1 d . . . . .
H7 H 0.666328 0.229875 0.462974 0.055 Uiso 1 1 calc R U . . .
C8 C 0.5642(4) 0.3294(2) 0.4432(6) 0.0521(11) Uani 1 1 d . . . . .
H8A H 0.578914 0.337986 0.325796 0.062 Uiso 1 1 calc R U . . .
H8B H 0.480162 0.344556 0.467305 0.062 Uiso 1 1 calc R U . . .
C9 C 0.6518(4) 0.3787(3) 0.5438(6) 0.0535(11) Uani 1 1 d . . . . .
C10 C 0.6376(4) 0.4643(2) 0.5375(5) 0.0465(10) Uani 1 1 d . . . . .
C11 C 0.5407(4) 0.5000(3) 0.4560(6) 0.0555(11) Uani 1 1 d . . . . .
H11 H 0.482192 0.470311 0.401112 0.067 Uiso 1 1 calc R U . . .
C12 C 0.5301(5) 0.5798(3) 0.4556(6) 0.0629(12) Uani 1 1 d . . . . .
H12 H 0.464407 0.603298 0.401562 0.076 Uiso 1 1 calc R U . . .
C13 C 0.6179(5) 0.6241(3) 0.5360(6) 0.0656(13) Uani 1 1 d . . . . .
H13 H 0.611412 0.677504 0.535630 0.079 Uiso 1 1 calc R U . . .
C14 C 0.7143(5) 0.5893(3) 0.6159(6) 0.0647(13) Uani 1 1 d . . . . .
H14 H 0.773336 0.619120 0.669273 0.078 Uiso 1 1 calc R U . . .
C15 C 0.7240(4) 0.5098(3) 0.6177(6) 0.0583(11) Uani 1 1 d . . . . .
H15 H 0.789267 0.486685 0.673325 0.070 Uiso 1 1 calc R U . . .
C16 C 0.5485(4) 0.2290(2) 0.6626(6) 0.0502(10) Uani 1 1 d . . . . .
C17 C 0.5835(6) 0.1498(4) 0.8937(7) 0.101(2) Uani 1 1 d . . . . .
H17A H 0.594775 0.192763 0.967197 0.152 Uiso 1 1 calc R U . . .
H17B H 0.634973 0.107892 0.928736 0.152 Uiso 1 1 calc R U . . .
H17C H 0.498902 0.133893 0.895996 0.152 Uiso 1 1 calc R U . . .
Cl1 Cl 0.25283(16) 0.02552(8) 0.1000(2) 0.0855(4) Uani 1 1 d . . . . .
O1 O 0.7313(3) 0.34942(19) 0.6280(6) 0.0864(13) Uani 1 1 d . . . . .
O2 O 0.4680(3) 0.26138(17) 0.7362(4) 0.0651(9) Uani 1 1 d . . . . .
O3 O 0.6166(3) 0.1723(2) 0.7263(5) 0.0752(10) 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 C2 1.380(6) . ?
C1 C6 1.383(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(6) . ?
C3 Cl1 1.738(4) . ?
C4 C5 1.385(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.523(6) . ?
C7 C16 1.519(6) . ?
C7 C8 1.523(6) . ?
C7 H7 0.9800 . ?
C8 C9 1.515(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O1 1.210(5) . ?
C9 C10 1.495(6) . ?
C10 C15 1.386(6) . ?
C10 C11 1.387(6) . ?
C11 C12 1.389(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 O2 1.197(5) . ?
C16 O3 1.334(5) . ?
C17 O3 1.448(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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 C1 C6 121.9(4) . . ?
C2 C1 H1 119.1 . . ?
C6 C1 H1 119.1 . . ?
C3 C2 C1 119.3(4) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 Cl1 119.4(4) . . ?
C2 C3 Cl1 119.8(4) . . ?
C3 C4 C5 119.2(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 121.6(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 117.2(4) . . ?
C1 C6 C7 120.4(4) . . ?
C5 C6 C7 122.2(4) . . ?
C16 C7 C6 107.0(3) . . ?
C16 C7 C8 109.7(3) . . ?
C6 C7 C8 113.9(3) . . ?
C16 C7 H7 108.7 . . ?
C6 C7 H7 108.7 . . ?
C8 C7 H7 108.7 . . ?
C9 C8 C7 111.7(4) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
O1 C9 C10 120.7(4) . . ?
O1 C9 C8 120.7(4) . . ?
C10 C9 C8 118.6(4) . . ?
C15 C10 C11 118.6(4) . . ?
C15 C10 C9 118.8(4) . . ?
C11 C10 C9 122.6(4) . . ?
C10 C11 C12 120.6(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 119.7(5) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 120.0(5) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.2(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 120.8(4) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
O2 C16 O3 124.2(4) . . ?
O2 C16 C7 124.0(4) . . ?
O3 C16 C7 111.7(4) . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 O3 C17 114.7(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H4 O2 0.93 2.57 3.428(5) 154.0 4_554 yes
C8 H8A O1 0.97 2.61 3.390(6) 137.4 4_654 yes
C17 H17B Cl1 0.96 2.98 3.925(6) 166.9 3_556 yes

_refine_diff_density_max         0.154
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.037




