# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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 2301324'
loop_
_audit_author_name
_audit_author_address
'Oscar Enrique Piro'
;Universidad Nacional de La Plata
Argentina
;
_audit_update_record             
;
2023-10-14 deposited with the CCDC.	2024-07-26 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
1-(5-chloro-2-hydroxyphenyl)-3-hydroxy-3-(naphthalen-1yl)prop-2-en-1-one
_chemical_name_common            ?
_chemical_melting_point          391
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H13 Cl O3'
_chemical_formula_weight         324.74
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'
O O 0.0106 0.0060 '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'

_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                   11.2130(10)
_cell_length_b                   7.9744(9)
_cell_length_c                   17.7754(14)
_cell_angle_alpha                90
_cell_angle_beta                 106.759(9)
_cell_angle_gamma                90
_cell_volume                     1521.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    926
_cell_measurement_theta_min      4.2940
_cell_measurement_theta_max      25.6550
_exptl_crystal_description       fragment
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.708
_exptl_crystal_size_mid          0.306
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.263
_shelx_estimated_absorpt_T_min   0.835
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_T_min  0.89260
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.885
_oxdiff_exptl_absorpt_empirical_full_max 1.180
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            4349
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.457
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measured_fraction_theta_full 0.905
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_Laue_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_point_group_measured_fraction_full 0.905
_reflns_number_total             2505
_reflns_number_gt                1658
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0660P)²+0.2174P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2505
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1533
_refine_ls_wR_factor_gt          0.1254
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
# start Validation Reply Form
_vrf_PLAT911_shelx               
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        255 Report
RESPONSE: Probably due to the shadow cast by the duo beamstops on the CCD.
;
# end Validation Reply Form  
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
Cl Cl 0.19587(10) 0.10778(12) 0.50346(5) 0.0959(4) Uani 1 1 d . . . . .
O1 O 0.5056(2) 0.6778(4) 0.65001(13) 0.0935(9) Uani 1 1 d . . . . .
O2 O 0.45366(17) 0.8145(3) 0.51229(10) 0.0738(6) Uani 1 1 d . . . . .
O3 O 0.39513(18) 0.9640(3) 0.37980(12) 0.0715(6) Uani 1 1 d . . . . .
C1 C 0.3677(2) 0.5533(4) 0.53223(14) 0.0549(7) Uani 1 1 d . . . . .
C2 C 0.4311(3) 0.5520(5) 0.61312(16) 0.0691(9) Uani 1 1 d . . . . .
C3 C 0.4198(3) 0.4145(6) 0.65884(19) 0.0767(11) Uani 1 1 d . . . . .
C4 C 0.3485(3) 0.2804(6) 0.6260(2) 0.0741(10) Uani 1 1 d . . . . .
C5 C 0.2861(3) 0.2790(4) 0.54631(16) 0.0646(8) Uani 1 1 d . . . . .
C6 C 0.2954(3) 0.4147(4) 0.50069(17) 0.0584(8) Uani 1 1 d . . . . .
C7 C 0.3788(2) 0.6989(4) 0.48294(15) 0.0544(7) Uani 1 1 d . . . . .
C8 C 0.3053(2) 0.7089(4) 0.40210(15) 0.0545(7) Uani 1 1 d . . . . .
C9 C 0.3160(2) 0.8390(4) 0.35510(14) 0.0517(7) Uani 1 1 d . . . . .
C10 C 0.2404(2) 0.8490(4) 0.27215(13) 0.0526(7) Uani 1 1 d . . . . .
C11 C 0.2312(3) 0.7099(5) 0.22649(18) 0.0712(9) Uani 1 1 d . . . . .
C12 C 0.1574(4) 0.7110(6) 0.1474(2) 0.0928(13) Uani 1 1 d . . . . .
C13 C 0.0943(4) 0.8505(6) 0.11608(18) 0.0853(12) Uani 1 1 d . . . . .
C14 C 0.0998(3) 0.9971(5) 0.16031(13) 0.0619(9) Uani 1 1 d . . . . .
C15 C 0.0312(3) 1.1435(6) 0.1284(2) 0.0772(12) Uani 1 1 d . . . . .
C16 C 0.0351(3) 1.2834(6) 0.1716(2) 0.0800(11) Uani 1 1 d . . . . .
C17 C 0.1074(3) 1.2843(5) 0.24949(19) 0.0709(9) Uani 1 1 d . . . . .
C18 C 0.1754(3) 1.1474(4) 0.28294(16) 0.0576(8) Uani 1 1 d . . . . .
C19 C 0.1750(2) 0.9992(4) 0.24000(13) 0.0499(7) Uani 1 1 d . . . . .
H1O H 0.508(4) 0.750(6) 0.615(2) 0.117(16) Uiso 1 1 d . . . . .
H3O H 0.439(3) 0.946(6) 0.435(2) 0.133(15) Uiso 1 1 d . . . . .
H3 H 0.466(3) 0.434(5) 0.7144(19) 0.091(10) Uiso 1 1 d . . . . .
H4 H 0.338(3) 0.194(5) 0.655(2) 0.100(12) Uiso 1 1 d . . . . .
H6 H 0.249(2) 0.412(4) 0.4483(16) 0.065(8) Uiso 1 1 d . . . . .
H8 H 0.243(2) 0.616(3) 0.3787(13) 0.050(6) Uiso 1 1 d . . . . .
H11 H 0.276(2) 0.613(4) 0.2499(15) 0.060(8) Uiso 1 1 d . . . . .
H12 H 0.162(3) 0.609(5) 0.1245(18) 0.086(11) Uiso 1 1 d . . . . .
H13 H 0.037(3) 0.850(5) 0.0622(19) 0.090(10) Uiso 1 1 d . . . . .
H15 H -0.016(3) 1.136(5) 0.080(2) 0.098(12) Uiso 1 1 d . . . . .
H16 H -0.015(4) 1.390(6) 0.146(2) 0.117(13) Uiso 1 1 d . . . . .
H17 H 0.115(3) 1.388(5) 0.282(2) 0.092(11) Uiso 1 1 d . . . . .
H18 H 0.219(2) 1.153(4) 0.3357(17) 0.077(9) Uiso 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
Cl C5 1.739(3) . ?
O1 C2 1.348(4) . ?
O2 C7 1.254(3) . ?
O3 C9 1.322(3) . ?
C1 C6 1.390(4) . ?
C1 C2 1.408(4) . ?
C1 C7 1.481(4) . ?
C2 C3 1.392(5) . ?
C3 C4 1.362(5) . ?
C4 C5 1.387(4) . ?
C5 C6 1.374(4) . ?
C7 C8 1.438(4) . ?
C8 C9 1.359(4) . ?
C9 C10 1.476(3) . ?
C10 C11 1.360(4) . ?
C10 C19 1.435(4) . ?
C11 C12 1.412(5) . ?
C12 C13 1.349(6) . ?
C13 C14 1.400(5) . ?
C14 C19 1.424(3) . ?
C14 C15 1.423(5) . ?
C15 C16 1.348(5) . ?
C16 C17 1.388(5) . ?
C17 C18 1.365(4) . ?
C18 C19 1.406(4) . ?

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 118.0(3) . . ?
C6 C1 C7 121.6(2) . . ?
C2 C1 C7 120.4(3) . . ?
O1 C2 C3 116.8(3) . . ?
O1 C2 C1 123.4(3) . . ?
C3 C2 C1 119.8(3) . . ?
C4 C3 C2 120.6(3) . . ?
C3 C4 C5 120.3(3) . . ?
C6 C5 C4 119.6(3) . . ?
C6 C5 Cl 119.6(2) . . ?
C4 C5 Cl 120.8(3) . . ?
C5 C6 C1 121.5(3) . . ?
O2 C7 C8 119.8(3) . . ?
O2 C7 C1 119.3(2) . . ?
C8 C7 C1 120.9(3) . . ?
C9 C8 C7 122.0(3) . . ?
O3 C9 C8 122.7(2) . . ?
O3 C9 C10 115.4(2) . . ?
C8 C9 C10 121.9(3) . . ?
C11 C10 C19 120.1(3) . . ?
C11 C10 C9 118.4(3) . . ?
C19 C10 C9 121.5(2) . . ?
C10 C11 C12 120.8(4) . . ?
C13 C12 C11 120.2(4) . . ?
C12 C13 C14 121.6(3) . . ?
C13 C14 C19 119.1(3) . . ?
C13 C14 C15 122.0(3) . . ?
C19 C14 C15 118.9(3) . . ?
C16 C15 C14 121.8(3) . . ?
C15 C16 C17 119.1(4) . . ?
C18 C17 C16 121.5(4) . . ?
C17 C18 C19 121.4(3) . . ?
C18 C19 C14 117.3(3) . . ?
C18 C19 C10 124.4(2) . . ?
C14 C19 C10 118.3(3) . . ?

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 O1 178.9(3) . . . . ?
C7 C1 C2 O1 -1.1(4) . . . . ?
C6 C1 C2 C3 -0.1(4) . . . . ?
C7 C1 C2 C3 179.9(3) . . . . ?
O1 C2 C3 C4 -178.6(3) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C3 C4 C5 Cl 179.4(3) . . . . ?
C4 C5 C6 C1 1.1(4) . . . . ?
Cl C5 C6 C1 -179.1(2) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
C7 C1 C6 C5 179.4(2) . . . . ?
C6 C1 C7 O2 -173.7(2) . . . . ?
C2 C1 C7 O2 6.3(4) . . . . ?
C6 C1 C7 C8 6.1(4) . . . . ?
C2 C1 C7 C8 -173.9(2) . . . . ?
O2 C7 C8 C9 1.5(4) . . . . ?
C1 C7 C8 C9 -178.3(3) . . . . ?
C7 C8 C9 O3 0.8(4) . . . . ?
C7 C8 C9 C10 -180.0(2) . . . . ?
O3 C9 C10 C11 132.4(3) . . . . ?
C8 C9 C10 C11 -46.8(4) . . . . ?
O3 C9 C10 C19 -49.1(3) . . . . ?
C8 C9 C10 C19 131.6(3) . . . . ?
C19 C10 C11 C12 -0.2(4) . . . . ?
C9 C10 C11 C12 178.2(3) . . . . ?
C10 C11 C12 C13 -0.3(5) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
C12 C13 C14 C19 0.7(5) . . . . ?
C12 C13 C14 C15 -178.4(3) . . . . ?
C13 C14 C15 C16 178.8(3) . . . . ?
C19 C14 C15 C16 -0.3(4) . . . . ?
C14 C15 C16 C17 -0.4(5) . . . . ?
C15 C16 C17 C18 0.7(5) . . . . ?
C16 C17 C18 C19 -0.2(5) . . . . ?
C17 C18 C19 C14 -0.6(4) . . . . ?
C17 C18 C19 C10 -177.6(3) . . . . ?
C13 C14 C19 C18 -178.4(3) . . . . ?
C15 C14 C19 C18 0.8(3) . . . . ?
C13 C14 C19 C10 -1.1(4) . . . . ?
C15 C14 C19 C10 178.0(2) . . . . ?
C11 C10 C19 C18 178.0(3) . . . . ?
C9 C10 C19 C18 -0.4(4) . . . . ?
C11 C10 C19 C14 0.9(4) . . . . ?
C9 C10 C19 C14 -177.5(2) . . . . ?

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
O1 H1O O2 0.86(5) 1.82(4) 2.588(3) 148(4) .
O1 H1O O3 0.86(5) 2.51(5) 3.165(4) 133(4) 3_676
O3 H3O O2 0.98(4) 1.70(4) 2.551(3) 144(4) .

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.034



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2323134'
loop_
_audit_author_name
_audit_author_address
'Oscar Enrique Piro'
;Universidad Nacional de La Plata
Argentina
;
_audit_update_record             
;
2024-01-20 deposited with the CCDC.	2024-07-26 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
1-(5-chloro-2-hidroxy-4-methylphenyl)-3-hydroxy-3-(3-naphthalen-1-yl)prop-2-en-1-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 Cl O3'
_chemical_formula_weight         338.77

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'
O O 0.0492 0.0322 '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'

_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                   3.8968(2)
_cell_length_b                   13.4160(12)
_cell_length_c                   30.1686(16)
_cell_angle_alpha                90
_cell_angle_beta                 87.761(5)
_cell_angle_gamma                90
_cell_volume                     1576.01(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1310
_cell_measurement_theta_min      3.6090
_cell_measurement_theta_max      71.7630
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.493
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.033
_exptl_absorpt_coefficient_mu    2.274
_shelx_estimated_absorpt_T_min   0.400
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_T_min  0.52170
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.653
_oxdiff_exptl_absorpt_empirical_full_max 1.546
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            11069
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         3.606
_diffrn_reflns_theta_max         72.255
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3077
_reflns_number_gt                2026
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0968P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3077
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1861
_refine_ls_wR_factor_gt          0.1584
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
Cl Cl 0.1945(3) 0.92594(8) -0.04828(3) 0.0881(4) Uani 1 1 d . . . . .
O1 O 0.3434(8) 0.55565(17) 0.05103(9) 0.0791(8) Uani 1 1 d . . . . .
H1 H 0.4422 0.5641 0.0742 0.119 Uiso 1 1 calc R U . . .
O2 O 0.6285(7) 0.65493(15) 0.11128(7) 0.0626(6) Uani 1 1 d . . . . .
O3 O 0.8370(7) 0.74387(15) 0.17704(7) 0.0601(6) Uani 1 1 d . . . . .
H3 H 0.7867 0.6965 0.1614 0.090 Uiso 1 1 calc R U . . .
C1 C 0.4089(7) 0.7352(2) 0.04867(9) 0.0450(6) Uani 1 1 d . . . . .
C2 C 0.3127(8) 0.6437(2) 0.02998(10) 0.0539(7) Uani 1 1 d . . . . .
C3 C 0.1729(8) 0.6415(3) -0.01210(11) 0.0586(8) Uani 1 1 d . . . . .
H3A H 0.1032 0.5807 -0.0235 0.070 Uiso 1 1 calc R U . . .
C4 C 0.1354(8) 0.7259(3) -0.03709(10) 0.0557(8) Uani 1 1 d . . . . .
C5 C 0.2330(8) 0.8165(2) -0.01809(10) 0.0536(7) Uani 1 1 d . . . . .
C6 C 0.3673(8) 0.8213(2) 0.02346(9) 0.0492(7) Uani 1 1 d . . . . .
H6 H 0.4311 0.8827 0.0348 0.059 Uiso 1 1 calc R U . . .
C7 C 0.5583(7) 0.7375(2) 0.09270(9) 0.0458(6) Uani 1 1 d . . . . .
C8 C 0.6204(7) 0.8286(2) 0.11574(9) 0.0443(6) Uani 1 1 d . . . . .
H8 H 0.5722 0.8892 0.1023 0.053 Uiso 1 1 calc R U . . .
C9 C 0.7503(7) 0.8279(2) 0.15749(9) 0.0444(6) Uani 1 1 d . . . . .
C10 C 0.8082(7) 0.9195(2) 0.18345(9) 0.0436(6) Uani 1 1 d . . . . .
C11 C 0.9595(7) 0.9997(2) 0.16256(10) 0.0499(7) Uani 1 1 d . . . . .
H11 H 1.0130 0.9963 0.1323 0.060 Uiso 1 1 calc R U . . .
C12 C 1.0354(8) 1.0869(2) 0.18594(12) 0.0567(8) Uani 1 1 d . . . . .
H12 H 1.1405 1.1403 0.1711 0.068 Uiso 1 1 calc R U . . .
C13 C 0.9561(8) 1.0938(2) 0.23013(11) 0.0555(8) Uani 1 1 d . . . . .
H13 H 1.0102 1.1515 0.2454 0.067 Uiso 1 1 calc R U . . .
C14 C 0.7920(7) 1.0139(2) 0.25300(10) 0.0479(7) Uani 1 1 d . . . . .
C15 C 0.7014(8) 1.0206(3) 0.29921(11) 0.0582(8) Uani 1 1 d . . . . .
H15 H 0.7549 1.0782 0.3146 0.070 Uiso 1 1 calc R U . . .
C16 C 0.5405(9) 0.9455(3) 0.32088(11) 0.0639(9) Uani 1 1 d . . . . .
H16 H 0.4826 0.9517 0.3510 0.077 Uiso 1 1 calc R U . . .
C17 C 0.4594(8) 0.8574(3) 0.29811(11) 0.0589(8) Uani 1 1 d . . . . .
H17 H 0.3494 0.8055 0.3134 0.071 Uiso 1 1 calc R U . . .
C18 C 0.5405(7) 0.8475(2) 0.25387(10) 0.0503(7) Uani 1 1 d . . . . .
H18 H 0.4806 0.7894 0.2392 0.060 Uiso 1 1 calc R U . . .
C19 C 0.7145(6) 0.9243(2) 0.22999(9) 0.0435(6) Uani 1 1 d . . . . .
C20 C -0.0079(10) 0.7205(3) -0.08253(12) 0.0770(11) Uani 1 1 d . . . . .
H20A H 0.1652 0.7404 -0.1043 0.116 Uiso 1 1 calc R U . . .
H20B H -0.2020 0.7643 -0.0840 0.116 Uiso 1 1 calc R U . . .
H20C H -0.0786 0.6534 -0.0884 0.116 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
Cl C5 1.737(3) . ?
O1 C2 1.349(4) . ?
O2 C7 1.276(3) . ?
O3 C9 1.323(3) . ?
C1 C6 1.396(4) . ?
C1 C2 1.408(4) . ?
C1 C7 1.471(4) . ?
C2 C3 1.401(4) . ?
C3 C4 1.371(5) . ?
C4 C5 1.403(4) . ?
C4 C20 1.502(4) . ?
C5 C6 1.379(4) . ?
C7 C8 1.432(4) . ?
C8 C9 1.376(4) . ?
C9 C10 1.480(4) . ?
C10 C11 1.368(4) . ?
C10 C19 1.438(4) . ?
C11 C12 1.404(4) . ?
C12 C13 1.360(5) . ?
C13 C14 1.414(4) . ?
C14 C15 1.428(4) . ?
C14 C19 1.426(4) . ?
C15 C16 1.343(5) . ?
C16 C17 1.409(5) . ?
C17 C18 1.366(4) . ?
C18 C19 1.416(4) . ?

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 117.7(3) . . ?
C6 C1 C7 122.2(2) . . ?
C2 C1 C7 120.1(3) . . ?
O1 C2 C3 116.9(3) . . ?
O1 C2 C1 123.0(3) . . ?
C3 C2 C1 120.0(3) . . ?
C4 C3 C2 122.3(3) . . ?
C3 C4 C5 117.1(3) . . ?
C3 C4 C20 120.9(3) . . ?
C5 C4 C20 122.1(3) . . ?
C6 C5 C4 122.0(3) . . ?
C6 C5 Cl 118.8(2) . . ?
C4 C5 Cl 119.2(2) . . ?
C5 C6 C1 120.9(3) . . ?
O2 C7 C8 119.0(3) . . ?
O2 C7 C1 118.5(2) . . ?
C8 C7 C1 122.4(2) . . ?
C9 C8 C7 120.9(3) . . ?
O3 C9 C8 121.6(3) . . ?
O3 C9 C10 115.2(2) . . ?
C8 C9 C10 123.2(2) . . ?
C11 C10 C19 120.2(3) . . ?
C11 C10 C9 118.8(3) . . ?
C19 C10 C9 121.0(2) . . ?
C10 C11 C12 121.3(3) . . ?
C13 C12 C11 120.3(3) . . ?
C12 C13 C14 120.6(3) . . ?
C15 C14 C13 121.3(3) . . ?
C15 C14 C19 118.7(3) . . ?
C13 C14 C19 120.1(3) . . ?
C16 C15 C14 121.4(3) . . ?
C15 C16 C17 120.1(3) . . ?
C18 C17 C16 120.7(3) . . ?
C17 C18 C19 120.9(3) . . ?
C14 C19 C18 118.2(3) . . ?
C14 C19 C10 117.5(3) . . ?
C18 C19 C10 124.2(3) . . ?

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 O1 179.5(3) . . . . ?
C7 C1 C2 O1 1.5(5) . . . . ?
C6 C1 C2 C3 -1.5(4) . . . . ?
C7 C1 C2 C3 -179.5(3) . . . . ?
O1 C2 C3 C4 -178.7(3) . . . . ?
C1 C2 C3 C4 2.3(5) . . . . ?
C2 C3 C4 C5 -2.1(5) . . . . ?
C2 C3 C4 C20 178.6(3) . . . . ?
C3 C4 C5 C6 1.3(5) . . . . ?
C20 C4 C5 C6 -179.4(3) . . . . ?
C3 C4 C5 Cl 179.5(2) . . . . ?
C20 C4 C5 Cl -1.2(5) . . . . ?
C4 C5 C6 C1 -0.6(5) . . . . ?
Cl C5 C6 C1 -178.9(2) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
C7 C1 C6 C5 178.7(3) . . . . ?
C6 C1 C7 O2 -171.2(3) . . . . ?
C2 C1 C7 O2 6.7(4) . . . . ?
C6 C1 C7 C8 10.2(4) . . . . ?
C2 C1 C7 C8 -171.9(3) . . . . ?
O2 C7 C8 C9 -0.7(4) . . . . ?
C1 C7 C8 C9 177.9(3) . . . . ?
C7 C8 C9 O3 3.1(4) . . . . ?
C7 C8 C9 C10 -177.8(3) . . . . ?
O3 C9 C10 C11 134.7(3) . . . . ?
C8 C9 C10 C11 -44.4(4) . . . . ?
O3 C9 C10 C19 -44.1(4) . . . . ?
C8 C9 C10 C19 136.8(3) . . . . ?
C19 C10 C11 C12 1.8(4) . . . . ?
C9 C10 C11 C12 -177.0(3) . . . . ?
C10 C11 C12 C13 -0.7(4) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C12 C13 C14 C15 -178.8(3) . . . . ?
C12 C13 C14 C19 1.3(4) . . . . ?
C13 C14 C15 C16 178.9(3) . . . . ?
C19 C14 C15 C16 -1.3(4) . . . . ?
C14 C15 C16 C17 0.4(5) . . . . ?
C15 C16 C17 C18 -0.4(5) . . . . ?
C16 C17 C18 C19 1.4(5) . . . . ?
C15 C14 C19 C18 2.1(4) . . . . ?
C13 C14 C19 C18 -178.1(2) . . . . ?
C15 C14 C19 C10 179.9(2) . . . . ?
C13 C14 C19 C10 -0.2(4) . . . . ?
C17 C18 C19 C14 -2.2(4) . . . . ?
C17 C18 C19 C10 -179.9(3) . . . . ?
C11 C10 C19 C14 -1.3(4) . . . . ?
C9 C10 C19 C14 177.4(2) . . . . ?
C11 C10 C19 C18 176.4(3) . . . . ?
C9 C10 C19 C18 -4.9(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
O1 H1 O2 0.82 1.82 2.544(3) 145.9 .
O3 H3 O2 0.82 1.75 2.479(3) 147.8 .

_refine_diff_density_max         0.348
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.073



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
