# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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 1994670'
loop_
_audit_author_name
_audit_author_address
'Alan Kennedy'
;University of Strathclyde
United Kingdom
;
_audit_update_record             
;
2021-09-03 deposited with the CCDC.	2022-03-08 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            'C16 H10 O6'
_chemical_formula_weight         298.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   13.653(5)
_cell_length_b                   5.286(2)
_cell_length_c                   17.808(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.77(5)
_cell_angle_gamma                90
_cell_volume                     1262.6(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    845
_cell_measurement_theta_min      4.49
_cell_measurement_theta_max      72.89

_exptl_crystal_description       'platey fragment'
_exptl_crystal_colour            yellow

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.036
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.65744
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6789
_diffrn_reflns_av_unetI/netI     0.1160
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         5.056
_diffrn_reflns_theta_max         67.499
_diffrn_reflns_theta_full        67.499
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measured_fraction_theta_full 0.912
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_Laue_measured_fraction_full 0.912
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_point_group_measured_fraction_full 0.912
_reflns_number_total             2082
_reflns_number_gt                1089
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
Even for a small plate, these crystals diffracted v weakly.

This required v long scan times that in turn led to bad icing 
of some runs. Discarding these leads to the low completeness %.


 


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
_computing_cell_refinement       CrysalisPro

_computing_data_reduction        CrysalisPro

_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL in WINGX'
_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)+(0.1341P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2082
_refine_ls_number_parameters     207
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1331
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.2197
_refine_ls_wR_factor_gt          0.1612
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_restrained_S_all      0.941
_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
O1 O 0.2177(2) -0.1666(7) 0.25409(18) 0.0291(8) Uani 1 1 d . . . . .
O2 O 0.1608(2) -0.2015(6) 0.36400(18) 0.0245(8) Uani 1 1 d . . . . .
O3 O 0.2339(3) 0.4245(6) 0.6137(2) 0.0288(9) Uani 1 1 d . . . . .
H1H H 0.211253 0.371702 0.651516 0.043 Uiso 1 1 calc R U . . .
O4 O 0.1204(2) 0.1503(6) 0.68139(19) 0.0282(8) Uani 1 1 d . . . . .
O5 O -0.0011(3) -0.2063(7) 0.6994(2) 0.0297(9) Uani 1 1 d D . . . .
H2H H -0.050(8) -0.31(2) 0.693(4) 0.045 Uiso 0.3148 1 d D U P . .
H3H H 0.013(5) -0.071(8) 0.726(3) 0.045 Uiso 0.6852 1 d D U P . .
O6 O 0.0148(2) -0.3935(7) 0.5901(2) 0.0323(9) Uani 1 1 d . . . . .
C1 C 0.2133(3) -0.0809(9) 0.3153(3) 0.0251(11) Uani 1 1 d . . . . .
C2 C 0.2594(3) 0.1667(9) 0.3510(3) 0.0210(10) Uani 1 1 d . . . . .
H2 H 0.227871 0.314845 0.320911 0.025 Uiso 1 1 calc R U . . .
C3 C 0.2273(3) 0.1570(9) 0.4278(3) 0.0211(10) Uani 1 1 d . . . . .
C4 C 0.1696(3) -0.0569(9) 0.4312(3) 0.0214(10) Uani 1 1 d . . . . .
C5 C 0.1272(3) -0.1175(9) 0.4921(3) 0.0227(11) Uani 1 1 d . . . . .
H5 H 0.086377 -0.263253 0.491588 0.027 Uiso 1 1 calc R U . . .
C6 C 0.1467(3) 0.0475(9) 0.5571(3) 0.0213(11) Uani 1 1 d . . . . .
C7 C 0.2077(3) 0.2634(9) 0.5545(3) 0.0220(10) Uani 1 1 d . . . . .
C8 C 0.2479(3) 0.3165(9) 0.4891(3) 0.0243(11) Uani 1 1 d . . . . .
H8 H 0.288826 0.461022 0.487536 0.029 Uiso 1 1 calc R U . . .
C9 C 0.3717(3) 0.1708(9) 0.3551(3) 0.0239(11) Uani 1 1 d . . . . .
C10 C 0.4144(4) 0.3586(10) 0.3176(3) 0.0339(13) Uani 1 1 d . . . . .
H10 H 0.374064 0.485161 0.289259 0.041 Uiso 1 1 calc R U . . .
C11 C 0.5175(4) 0.3593(11) 0.3221(4) 0.0426(16) Uani 1 1 d . . . . .
H11 H 0.547478 0.487795 0.296715 0.051 Uiso 1 1 calc R U . . .
C12 C 0.5763(4) 0.1761(11) 0.3630(3) 0.0374(14) Uani 1 1 d . . . . .
H12 H 0.646510 0.178831 0.365952 0.045 Uiso 1 1 calc R U . . .
C13 C 0.5327(4) -0.0131(12) 0.3999(3) 0.0428(15) Uani 1 1 d . . . . .
H13 H 0.572750 -0.140752 0.427931 0.051 Uiso 1 1 calc R U . . .
C14 C 0.4292(4) -0.0138(10) 0.3954(3) 0.0323(12) Uani 1 1 d . . . . .
H14 H 0.398773 -0.142730 0.420303 0.039 Uiso 1 1 calc R U . . .
C15 C 0.1044(3) 0.0053(9) 0.6254(3) 0.0228(11) Uani 1 1 d . . . . .
C16 C 0.0356(3) -0.2220(10) 0.6345(3) 0.0278(12) Uani 1 1 d 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
O1 C1 1.192(6) . ?
O2 C1 1.381(5) . ?
O2 C4 1.407(6) . ?
O3 C7 1.350(6) . ?
O3 H1H 0.8400 . ?
O4 C15 1.244(6) . ?
O5 C16 1.346(6) . ?
O5 H2H 0.851(11) . ?
O5 H3H 0.858(10) . ?
O6 C16 1.201(6) . ?
C1 C2 1.538(7) . ?
C2 C3 1.512(6) . ?
C2 C9 1.522(6) . ?
C2 H2 1.0000 . ?
C3 C8 1.366(7) . ?
C3 C4 1.386(6) . ?
C4 C5 1.358(6) . ?
C5 C6 1.434(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.419(6) . ?
C6 C15 1.458(6) . ?
C7 C8 1.405(6) . ?
C8 H8 0.9500 . ?
C9 C14 1.368(7) . ?
C9 C10 1.383(7) . ?
C10 C11 1.395(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.400(7) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.552(7) . ?

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
C1 O2 C4 108.2(4) . . ?
C7 O3 H1H 109.5 . . ?
C16 O5 H2H 104.2(13) . . ?
C16 O5 H3H 116.6(15) . . ?
H2H O5 H3H 134(6) . . ?
O1 C1 O2 121.3(4) . . ?
O1 C1 C2 128.0(4) . . ?
O2 C1 C2 110.7(4) . . ?
C3 C2 C9 114.7(4) . . ?
C3 C2 C1 100.4(4) . . ?
C9 C2 C1 111.3(4) . . ?
C3 C2 H2 110.0 . . ?
C9 C2 H2 110.0 . . ?
C1 C2 H2 110.0 . . ?
C8 C3 C4 120.1(4) . . ?
C8 C3 C2 130.5(4) . . ?
C4 C3 C2 109.3(4) . . ?
C5 C4 C3 123.9(5) . . ?
C5 C4 O2 124.7(4) . . ?
C3 C4 O2 111.4(4) . . ?
C4 C5 C6 117.2(4) . . ?
C4 C5 H5 121.4 . . ?
C6 C5 H5 121.4 . . ?
C7 C6 C5 119.0(4) . . ?
C7 C6 C15 118.5(4) . . ?
C5 C6 C15 122.5(4) . . ?
O3 C7 C8 115.7(4) . . ?
O3 C7 C6 123.6(4) . . ?
C8 C7 C6 120.7(4) . . ?
C3 C8 C7 119.0(4) . . ?
C3 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C14 C9 C10 120.9(5) . . ?
C14 C9 C2 119.2(4) . . ?
C10 C9 C2 119.9(5) . . ?
C9 C10 C11 119.1(5) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C12 C11 C10 120.7(5) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 119.8(5) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 119.5(5) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C9 C14 C13 120.1(5) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
O4 C15 C6 122.5(4) . . ?
O4 C15 C16 114.4(4) . . ?
C6 C15 C16 123.2(4) . . ?
O6 C16 O5 122.1(5) . . ?
O6 C16 C15 126.1(4) . . ?
O5 C16 C15 111.8(5) . . ?

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
C4 O2 C1 O1 179.8(5) . . . . ?
C4 O2 C1 C2 -1.3(5) . . . . ?
O1 C1 C2 C3 -179.1(5) . . . . ?
O2 C1 C2 C3 2.1(5) . . . . ?
O1 C1 C2 C9 -57.3(7) . . . . ?
O2 C1 C2 C9 123.9(4) . . . . ?
C9 C2 C3 C8 57.3(7) . . . . ?
C1 C2 C3 C8 176.6(5) . . . . ?
C9 C2 C3 C4 -121.4(4) . . . . ?
C1 C2 C3 C4 -2.1(5) . . . . ?
C8 C3 C4 C5 2.7(7) . . . . ?
C2 C3 C4 C5 -178.4(4) . . . . ?
C8 C3 C4 O2 -177.3(4) . . . . ?
C2 C3 C4 O2 1.5(5) . . . . ?
C1 O2 C4 C5 179.8(4) . . . . ?
C1 O2 C4 C3 -0.1(5) . . . . ?
C3 C4 C5 C6 -2.1(7) . . . . ?
O2 C4 C5 C6 178.0(4) . . . . ?
C4 C5 C6 C7 0.4(7) . . . . ?
C4 C5 C6 C15 179.1(4) . . . . ?
C5 C6 C7 O3 -177.1(4) . . . . ?
C15 C6 C7 O3 4.2(7) . . . . ?
C5 C6 C7 C8 0.5(7) . . . . ?
C15 C6 C7 C8 -178.2(4) . . . . ?
C4 C3 C8 C7 -1.6(7) . . . . ?
C2 C3 C8 C7 179.8(5) . . . . ?
O3 C7 C8 C3 177.9(4) . . . . ?
C6 C7 C8 C3 0.1(7) . . . . ?
C3 C2 C9 C14 53.9(6) . . . . ?
C1 C2 C9 C14 -59.2(6) . . . . ?
C3 C2 C9 C10 -126.7(5) . . . . ?
C1 C2 C9 C10 120.2(5) . . . . ?
C14 C9 C10 C11 -0.7(8) . . . . ?
C2 C9 C10 C11 179.9(5) . . . . ?
C9 C10 C11 C12 0.2(9) . . . . ?
C10 C11 C12 C13 0.4(9) . . . . ?
C11 C12 C13 C14 -0.4(9) . . . . ?
C10 C9 C14 C13 0.7(8) . . . . ?
C2 C9 C14 C13 -179.9(5) . . . . ?
C12 C13 C14 C9 -0.2(9) . . . . ?
C7 C6 C15 O4 -0.5(7) . . . . ?
C5 C6 C15 O4 -179.1(4) . . . . ?
C7 C6 C15 C16 179.2(4) . . . . ?
C5 C6 C15 C16 0.5(7) . . . . ?
O4 C15 C16 O6 -175.2(5) . . . . ?
C6 C15 C16 O6 5.1(8) . . . . ?
O4 C15 C16 O5 5.4(6) . . . . ?
C6 C15 C16 O5 -174.2(4) . . . . ?

_refine_diff_density_max         0.452
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.117

