# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 1990308'
loop_
_audit_author_name
_audit_author_address
'Magda Monari'
;University of Bologna
Italy
;
_audit_update_record             
;
2020-03-13 deposited with the CCDC.	2020-06-17 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_shelx               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: The crystal did not diffract to high angles. The crystal quality
was poor and the experiment was carried out on a small crystal
;
# end Validation Reply Form 
_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            'C16 H12 O3'
_chemical_formula_weight         252.26

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   5.865(2)
_cell_length_b                   14.967(5)
_cell_length_c                   14.978(5)
_cell_angle_alpha                72.081(10)
_cell_angle_beta                 82.356(12)
_cell_angle_gamma                84.576(12)
_cell_volume                     1237.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9938
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      68.31

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.762
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD Bruker Apex area detector'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3632
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         3.108
_diffrn_reflns_theta_max         60.975
_diffrn_reflns_theta_full        50.000
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.951
_reflns_number_total             3632
_reflns_number_gt                2995
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.2000P)²] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.25(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3632
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1277
_refine_ls_R_factor_gt           0.1123
_refine_ls_wR_factor_ref         0.2837
_refine_ls_wR_factor_gt          0.2647
_refine_ls_goodness_of_fit_ref   1.240
_refine_ls_restrained_S_all      1.240
_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
O1B O -0.0539(4) 0.89716(16) -0.11234(16) 0.0442(7) Uani 1 1 d . . . . .
O3B O 0.4953(4) 0.76126(14) 0.00536(14) 0.0344(7) Uani 1 1 d . . . . .
O1A O 0.4797(4) 0.46976(16) 0.34841(16) 0.0425(7) Uani 1 1 d . . . . .
O3A O 1.0443(4) 0.61471(14) 0.27756(14) 0.0350(7) Uani 1 1 d . . . . .
O2B O 0.2287(4) 0.78618(15) -0.10412(14) 0.0378(7) Uani 1 1 d . . . . .
O2A O 0.7793(4) 0.52481(15) 0.24380(14) 0.0380(7) Uani 1 1 d . . . . .
C3B C 0.4628(6) 0.7683(2) -0.0898(2) 0.0358(8) Uani 1 1 d . . . . .
H3B H 0.553281 0.820492 -0.134253 0.043 Uiso 1 1 calc R U . . .
C5A C 0.7698(6) 0.5376(2) 0.3988(2) 0.0373(8) Uani 1 1 d . . . . .
H5A H 0.718906 0.516148 0.464335 0.045 Uiso 1 1 calc R U . . .
C3A C 1.0157(6) 0.5408(2) 0.2381(2) 0.0355(8) Uani 1 1 d . . . . .
H3A H 1.100366 0.481735 0.272629 0.043 Uiso 1 1 calc R U . . .
C4A C 0.6625(6) 0.5056(2) 0.3337(2) 0.0353(8) Uani 1 1 d . . . . .
C9A C 0.9876(5) 0.7136(2) 0.5550(2) 0.0338(8) Uani 1 1 d . . . . .
C7A C 1.0295(5) 0.6526(2) 0.4207(2) 0.0326(8) Uani 1 1 d . . . . .
C1A C 1.0047(7) 0.5747(3) 0.0659(2) 0.0503(10) Uani 1 1 d . . . . .
H1A H 0.850513 0.556041 0.077275 0.060 Uiso 1 1 calc R U . . .
H1B H 1.077810 0.595271 0.003144 0.060 Uiso 1 1 calc R U . . .
C5B C 0.2505(5) 0.8983(2) -0.0229(2) 0.0355(8) Uani 1 1 d . . . . .
H5B H 0.216974 0.960158 -0.018194 0.043 Uiso 1 1 calc R U . . .
C12B C 0.7006(6) 0.9571(2) 0.3793(2) 0.0382(9) Uani 1 1 d . . . . .
H12B H 0.766779 0.966293 0.430153 0.046 Uiso 1 1 calc R U . . .
C1B C 0.4417(6) 0.6328(2) -0.1510(2) 0.0416(9) Uani 1 1 d . . . . .
H1D H 0.297992 0.658255 -0.173185 0.050 Uiso 1 1 calc R U . . .
H1C H 0.506658 0.575198 -0.160071 0.050 Uiso 1 1 calc R U . . .
C6A C 0.9410(5) 0.5972(2) 0.3680(2) 0.0332(8) Uani 1 1 d . . . . .
C11B C 0.4859(6) 1.0011(2) 0.3564(2) 0.0381(9) Uani 1 1 d . . . . .
H11B H 0.407083 1.039570 0.392007 0.046 Uiso 1 1 calc R U . . .
C4B C 0.1268(6) 0.8659(2) -0.0835(2) 0.0348(8) Uani 1 1 d . . . . .
C9B C 0.5026(5) 0.9305(2) 0.2294(2) 0.0312(8) Uani 1 1 d . . . . .
C7B C 0.5156(5) 0.8561(2) 0.1053(2) 0.0316(8) Uani 1 1 d . . . . .
C6B C 0.4115(6) 0.8425(2) 0.0267(2) 0.0336(8) Uani 1 1 d . . . . .
C10B C 0.3880(6) 0.9889(2) 0.2825(2) 0.0359(8) Uani 1 1 d . . . . .
H10B H 0.242945 1.019680 0.266992 0.043 Uiso 1 1 calc R U . . .
C8A C 0.9034(5) 0.6636(2) 0.5014(2) 0.0330(8) Uani 1 1 d . . . . .
H8A H 0.757459 0.637041 0.521325 0.040 Uiso 1 1 calc R U . . .
C8B C 0.4031(6) 0.9151(2) 0.1548(2) 0.0328(8) Uani 1 1 d . . . . .
H8B H 0.258082 0.945345 0.138450 0.039 Uiso 1 1 calc R U . . .
C10A C 0.8622(6) 0.7240(2) 0.6391(2) 0.0380(8) Uani 1 1 d . . . . .
H10A H 0.717528 0.696718 0.660822 0.046 Uiso 1 1 calc R U . . .
C14A C 1.2046(5) 0.7547(2) 0.5230(2) 0.0330(8) Uani 1 1 d . . . . .
C12A C 1.1644(6) 0.8139(2) 0.6581(2) 0.0431(9) Uani 1 1 d . . . . .
H12A H 1.223991 0.847281 0.693697 0.052 Uiso 1 1 calc R U . . .
C16A C 1.2463(5) 0.6933(2) 0.3892(2) 0.0340(8) Uani 1 1 d . . . . .
H16A H 1.333175 0.685705 0.333575 0.041 Uiso 1 1 calc R U . . .
C13B C 0.8178(6) 0.9003(2) 0.3289(2) 0.0362(8) Uani 1 1 d . . . . .
H13B H 0.963579 0.870736 0.344896 0.043 Uiso 1 1 calc R U . . .
C13A C 1.2866(6) 0.8055(2) 0.5770(2) 0.0394(9) Uani 1 1 d . . . . .
H13A H 1.429794 0.834116 0.556048 0.047 Uiso 1 1 calc R U . . .
C16B C 0.7312(5) 0.8110(2) 0.1297(2) 0.0338(8) Uani 1 1 d . . . . .
H16B H 0.807052 0.770011 0.096345 0.041 Uiso 1 1 calc R U . . .
C15A C 1.3298(6) 0.7433(2) 0.4389(2) 0.0358(8) Uani 1 1 d . . . . .
H15A H 1.473955 0.770939 0.416909 0.043 Uiso 1 1 calc R U . . .
C2B C 0.5506(6) 0.6771(2) -0.1077(2) 0.0397(9) Uani 1 1 d . . . . .
H2B H 0.693903 0.649747 -0.086314 0.048 Uiso 1 1 calc R U . . .
C14B C 0.7187(6) 0.8865(2) 0.2530(2) 0.0348(8) Uani 1 1 d . . . . .
C2A C 1.1161(6) 0.5722(2) 0.1366(2) 0.0411(9) Uani 1 1 d . . . . .
H2A H 1.270081 0.591271 0.123017 0.049 Uiso 1 1 calc R U . . .
C15B C 0.8317(6) 0.8259(2) 0.2010(2) 0.0348(8) Uani 1 1 d . . . . .
H15B H 0.977664 0.795799 0.216042 0.042 Uiso 1 1 calc R U . . .
C11A C 0.9491(6) 0.7733(2) 0.6896(2) 0.0419(9) Uani 1 1 d . . . . .
H11A H 0.863841 0.780055 0.745908 0.050 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
O1B C4B 1.197(4) . ?
O3B C6B 1.380(4) . ?
O3B C3B 1.434(4) . ?
O1A C4A 1.208(4) . ?
O3A C6A 1.365(4) . ?
O3A C3A 1.437(4) . ?
O2B C4B 1.386(4) . ?
O2B C3B 1.406(4) . ?
O2A C4A 1.385(4) . ?
O2A C3A 1.416(4) . ?
C3B C2B 1.501(4) . ?
C3B H3B 1.0000 . ?
C5A C6A 1.345(5) . ?
C5A C4A 1.443(5) . ?
C5A H5A 0.9500 . ?
C3A C2A 1.501(5) . ?
C3A H3A 1.0000 . ?
C9A C8A 1.413(4) . ?
C9A C10A 1.415(4) . ?
C9A C14A 1.425(5) . ?
C7A C8A 1.377(4) . ?
C7A C16A 1.421(4) . ?
C7A C6A 1.474(4) . ?
C1A C2A 1.305(5) . ?
C1A H1A 0.9500 . ?
C1A H1B 0.9500 . ?
C5B C6B 1.340(5) . ?
C5B C4B 1.448(5) . ?
C5B H5B 0.9500 . ?
C12B C13B 1.382(5) . ?
C12B C11B 1.399(5) . ?
C12B H12B 0.9500 . ?
C1B C2B 1.312(5) . ?
C1B H1D 0.9500 . ?
C1B H1C 0.9500 . ?
C11B C10B 1.379(5) . ?
C11B H11B 0.9500 . ?
C9B C14B 1.408(5) . ?
C9B C8B 1.414(4) . ?
C9B C10B 1.422(4) . ?
C7B C8B 1.388(4) . ?
C7B C16B 1.414(5) . ?
C7B C6B 1.471(4) . ?
C10B H10B 0.9500 . ?
C8A H8A 0.9500 . ?
C8B H8B 0.9500 . ?
C10A C11A 1.375(5) . ?
C10A H10A 0.9500 . ?
C14A C13A 1.418(5) . ?
C14A C15A 1.420(5) . ?
C12A C13A 1.361(5) . ?
C12A C11A 1.413(5) . ?
C12A H12A 0.9500 . ?
C16A C15A 1.365(5) . ?
C16A H16A 0.9500 . ?
C13B C14B 1.420(5) . ?
C13B H13B 0.9500 . ?
C13A H13A 0.9500 . ?
C16B C15B 1.369(5) . ?
C16B H16B 0.9500 . ?
C15A H15A 0.9500 . ?
C2B H2B 0.9500 . ?
C14B C15B 1.432(4) . ?
C2A H2A 0.9500 . ?
C15B H15B 0.9500 . ?
C11A H11A 0.9500 . ?

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
C6B O3B C3B 110.7(2) . . ?
C6A O3A C3A 112.1(2) . . ?
C4B O2B C3B 114.6(2) . . ?
C4A O2A C3A 114.9(2) . . ?
O2B C3B O3B 110.9(2) . . ?
O2B C3B C2B 110.0(3) . . ?
O3B C3B C2B 108.1(2) . . ?
O2B C3B H3B 109.3 . . ?
O3B C3B H3B 109.3 . . ?
C2B C3B H3B 109.3 . . ?
C6A C5A C4A 120.9(3) . . ?
C6A C5A H5A 119.5 . . ?
C4A C5A H5A 119.5 . . ?
O2A C3A O3A 110.6(2) . . ?
O2A C3A C2A 109.9(3) . . ?
O3A C3A C2A 107.0(2) . . ?
O2A C3A H3A 109.8 . . ?
O3A C3A H3A 109.8 . . ?
C2A C3A H3A 109.8 . . ?
O1A C4A O2A 118.4(3) . . ?
O1A C4A C5A 126.8(3) . . ?
O2A C4A C5A 114.6(3) . . ?
C8A C9A C10A 121.8(3) . . ?
C8A C9A C14A 118.8(3) . . ?
C10A C9A C14A 119.5(3) . . ?
C8A C7A C16A 120.0(3) . . ?
C8A C7A C6A 119.8(3) . . ?
C16A C7A C6A 120.2(3) . . ?
C2A C1A H1A 120.0 . . ?
C2A C1A H1B 120.0 . . ?
H1A C1A H1B 120.0 . . ?
C6B C5B C4B 121.1(3) . . ?
C6B C5B H5B 119.4 . . ?
C4B C5B H5B 119.4 . . ?
C13B C12B C11B 120.8(3) . . ?
C13B C12B H12B 119.6 . . ?
C11B C12B H12B 119.6 . . ?
C2B C1B H1D 120.0 . . ?
C2B C1B H1C 120.0 . . ?
H1D C1B H1C 120.0 . . ?
C5A C6A O3A 119.9(3) . . ?
C5A C6A C7A 127.0(3) . . ?
O3A C6A C7A 113.1(3) . . ?
C10B C11B C12B 120.4(3) . . ?
C10B C11B H11B 119.8 . . ?
C12B C11B H11B 119.8 . . ?
O1B C4B O2B 118.4(3) . . ?
O1B C4B C5B 127.5(3) . . ?
O2B C4B C5B 114.0(3) . . ?
C14B C9B C8B 119.7(3) . . ?
C14B C9B C10B 118.8(3) . . ?
C8B C9B C10B 121.5(3) . . ?
C8B C7B C16B 119.8(3) . . ?
C8B C7B C6B 119.7(3) . . ?
C16B C7B C6B 120.5(3) . . ?
C5B C6B O3B 119.4(3) . . ?
C5B C6B C7B 127.6(3) . . ?
O3B C6B C7B 113.1(3) . . ?
C11B C10B C9B 120.4(3) . . ?
C11B C10B H10B 119.8 . . ?
C9B C10B H10B 119.8 . . ?
C7A C8A C9A 121.1(3) . . ?
C7A C8A H8A 119.5 . . ?
C9A C8A H8A 119.5 . . ?
C7B C8B C9B 120.5(3) . . ?
C7B C8B H8B 119.7 . . ?
C9B C8B H8B 119.7 . . ?
C11A C10A C9A 120.3(3) . . ?
C11A C10A H10A 119.9 . . ?
C9A C10A H10A 119.9 . . ?
C13A C14A C15A 122.7(3) . . ?
C13A C14A C9A 118.3(3) . . ?
C15A C14A C9A 119.0(3) . . ?
C13A C12A C11A 120.3(3) . . ?
C13A C12A H12A 119.9 . . ?
C11A C12A H12A 119.9 . . ?
C15A C16A C7A 120.1(3) . . ?
C15A C16A H16A 119.9 . . ?
C7A C16A H16A 119.9 . . ?
C12B C13B C14B 119.6(3) . . ?
C12B C13B H13B 120.2 . . ?
C14B C13B H13B 120.2 . . ?
C12A C13A C14A 121.3(3) . . ?
C12A C13A H13A 119.3 . . ?
C14A C13A H13A 119.3 . . ?
C15B C16B C7B 120.6(3) . . ?
C15B C16B H16B 119.7 . . ?
C7B C16B H16B 119.7 . . ?
C16A C15A C14A 121.1(3) . . ?
C16A C15A H15A 119.5 . . ?
C14A C15A H15A 119.5 . . ?
C1B C2B C3B 124.1(3) . . ?
C1B C2B H2B 117.9 . . ?
C3B C2B H2B 117.9 . . ?
C9B C14B C13B 120.0(3) . . ?
C9B C14B C15B 118.8(3) . . ?
C13B C14B C15B 121.2(3) . . ?
C1A C2A C3A 123.9(3) . . ?
C1A C2A H2A 118.0 . . ?
C3A C2A H2A 118.0 . . ?
C16B C15B C14B 120.6(3) . . ?
C16B C15B H15B 119.7 . . ?
C14B C15B H15B 119.7 . . ?
C10A C11A C12A 120.3(3) . . ?
C10A C11A H11A 119.8 . . ?
C12A C11A H11A 119.8 . . ?

_refine_diff_density_max         0.553
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.142



