# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_150610a
_database_code_depnum_ccdc_archive 'CCDC 1575314'
_audit_update_record             
;
2017-09-19 deposited with the CCDC.
2017-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 O7'
_chemical_formula_weight         318.27

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9340(5)
_cell_length_b                   9.4461(8)
_cell_length_c                   12.5549(11)
_cell_angle_alpha                77.7590(10)
_cell_angle_beta                 76.1000(10)
_cell_angle_gamma                88.981(2)
_cell_volume                     779.63(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    798
_cell_measurement_theta_min      2.225
_cell_measurement_theta_max      28.289

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9777
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3940
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_sigmaI/netI    0.0911
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2682
_reflns_number_gt                1243
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1178P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2682
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1689
_refine_ls_R_factor_gt           0.1071
_refine_ls_wR_factor_ref         0.2612
_refine_ls_wR_factor_gt          0.2366
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7116(5) 0.2731(3) 0.0741(2) 0.0547(10) Uani 1 1 d . . .
O2 O 0.5785(7) 0.2408(4) 0.2569(3) 0.0783(14) Uani 1 1 d . . .
O3 O 0.6548(7) -0.1113(4) 0.3541(3) 0.0703(12) Uani 1 1 d . . .
O4 O 0.3450(7) -0.0766(4) 0.3310(3) 0.0696(12) Uani 1 1 d . . .
O5 O 0.6126(6) -0.2631(3) 0.1831(3) 0.0587(11) Uani 1 1 d . . .
O6 O 0.7431(7) -0.2243(4) -0.0019(3) 0.0809(14) Uani 1 1 d . . .
O7 O 1.0076(7) 0.6693(4) -0.4102(3) 0.0733(13) Uani 1 1 d . . .
C1 C 0.6331(8) 0.1833(5) 0.1788(4) 0.0523(14) Uani 1 1 d . . .
C2 C 0.6236(8) 0.0282(5) 0.1823(4) 0.0466(13) Uani 1 1 d . . .
C3 C 0.6905(7) -0.0215(5) 0.0856(4) 0.0454(12) Uani 1 1 d . . .
C4 C 0.7657(7) 0.0783(5) -0.0185(4) 0.0465(13) Uani 1 1 d . . .
H4 H 0.8099 0.0435 -0.0839 0.056 Uiso 1 1 calc R . .
C5 C 0.7738(7) 0.2217(5) -0.0237(4) 0.0446(13) Uani 1 1 d . . .
C6 C 0.8422(7) 0.3396(5) -0.1218(4) 0.0426(12) Uani 1 1 d . . .
C7 C 0.8969(8) 0.3107(5) -0.2306(4) 0.0528(14) Uani 1 1 d . . .
H7 H 0.8968 0.2155 -0.2396 0.063 Uiso 1 1 calc R . .
C8 C 0.9510(9) 0.4234(5) -0.3244(4) 0.0598(15) Uani 1 1 d . . .
H8 H 0.9864 0.4033 -0.3959 0.072 Uiso 1 1 calc R . .
C9 C 0.9522(8) 0.5670(5) -0.3117(4) 0.0526(14) Uani 1 1 d . . .
C10 C 0.8980(8) 0.5990(5) -0.2063(4) 0.0528(14) Uani 1 1 d . . .
H10 H 0.8972 0.6946 -0.1981 0.063 Uiso 1 1 calc R . .
C11 C 0.8441(7) 0.4844(5) -0.1120(4) 0.0497(14) Uani 1 1 d . . .
H11 H 0.8087 0.5054 -0.0409 0.060 Uiso 1 1 calc R . .
C12 C 0.5241(10) -0.0603(5) 0.2974(4) 0.0513(14) Uani 1 1 d . . .
C13 C 0.5696(12) -0.2042(8) 0.4662(5) 0.103(3) Uani 1 1 d . . .
H13A H 0.4863 -0.1476 0.5130 0.155 Uiso 1 1 calc R . .
H13B H 0.6752 -0.2422 0.5001 0.155 Uiso 1 1 calc R . .
H13C H 0.4920 -0.2827 0.4583 0.155 Uiso 1 1 calc R . .
C14 C 0.6856(8) -0.1816(5) 0.0830(4) 0.0483(13) Uani 1 1 d . . .
C15 C 0.6079(9) -0.4205(5) 0.1946(5) 0.0633(16) Uani 1 1 d . . .
H15A H 0.5411 -0.4452 0.1420 0.095 Uiso 1 1 calc R . .
H15B H 0.5381 -0.4659 0.2696 0.095 Uiso 1 1 calc R . .
H15C H 0.7414 -0.4538 0.1798 0.095 Uiso 1 1 calc R . .
C16 C 1.0106(10) 0.8191(6) -0.4029(5) 0.079(2) Uani 1 1 d . . .
H16A H 0.8797 0.8447 -0.3679 0.118 Uiso 1 1 calc R . .
H16B H 1.0527 0.8788 -0.4770 0.118 Uiso 1 1 calc R . .
H16C H 1.1014 0.8338 -0.3590 0.118 Uiso 1 1 calc R . .


_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 C5 1.385(5) . ?
O1 C1 1.394(5) . ?
O2 C1 1.200(6) . ?
O3 C12 1.308(6) . ?
O3 C13 1.481(6) . ?
O4 C12 1.213(6) . ?
O5 C14 1.313(5) . ?
O5 C15 1.464(5) . ?
O6 C14 1.196(5) . ?
O7 C9 1.375(5) . ?
O7 C16 1.438(6) . ?
C1 C2 1.459(6) . ?
C2 C3 1.369(6) . ?
C2 C12 1.514(6) . ?
C3 C4 1.428(6) . ?
C3 C14 1.521(6) . ?
C4 C5 1.344(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.461(6) . ?
C6 C11 1.400(6) . ?
C6 C7 1.411(6) . ?
C7 C8 1.390(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.400(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.381(6) . ?
C10 C11 1.404(6) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C5 O1 C1 123.2(3) . . ?
C12 O3 C13 114.7(5) . . ?
C14 O5 C15 118.2(4) . . ?
C9 O7 C16 117.8(4) . . ?
O2 C1 O1 117.1(4) . . ?
O2 C1 C2 126.4(4) . . ?
O1 C1 C2 116.5(4) . . ?
C3 C2 C1 119.7(4) . . ?
C3 C2 C12 127.1(4) . . ?
C1 C2 C12 113.1(4) . . ?
C2 C3 C4 120.1(4) . . ?
C2 C3 C14 122.6(4) . . ?
C4 C3 C14 117.3(4) . . ?
C5 C4 C3 121.1(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 O1 119.3(4) . . ?
C4 C5 C6 128.9(4) . . ?
O1 C5 C6 111.7(4) . . ?
C11 C6 C7 117.9(4) . . ?
C11 C6 C5 121.6(4) . . ?
C7 C6 C5 120.4(4) . . ?
C8 C7 C6 120.6(4) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.1(4) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
O7 C9 C10 124.2(4) . . ?
O7 C9 C8 115.1(4) . . ?
C10 C9 C8 120.7(4) . . ?
C9 C10 C11 118.7(4) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C6 C11 C10 122.0(4) . . ?
C6 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
O4 C12 O3 125.9(5) . . ?
O4 C12 C2 122.7(5) . . ?
O3 C12 C2 111.4(5) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O6 C14 O5 125.7(4) . . ?
O6 C14 C3 122.3(4) . . ?
O5 C14 C3 112.1(4) . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O7 C16 H16A 109.5 . . ?
O7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
C5 O1 C1 O2 -177.7(5) . . . . ?
C5 O1 C1 C2 1.7(7) . . . . ?
O2 C1 C2 C3 179.4(6) . . . . ?
O1 C1 C2 C3 0.1(8) . . . . ?
O2 C1 C2 C12 3.2(8) . . . . ?
O1 C1 C2 C12 -176.1(5) . . . . ?
C1 C2 C3 C4 -1.2(8) . . . . ?
C12 C2 C3 C4 174.5(5) . . . . ?
C1 C2 C3 C14 179.8(4) . . . . ?
C12 C2 C3 C14 -4.5(9) . . . . ?
C2 C3 C4 C5 0.5(8) . . . . ?
C14 C3 C4 C5 179.5(5) . . . . ?
C3 C4 C5 O1 1.3(7) . . . . ?
C3 C4 C5 C6 -178.9(5) . . . . ?
C1 O1 C5 C4 -2.4(7) . . . . ?
C1 O1 C5 C6 177.7(4) . . . . ?
C4 C5 C6 C11 -178.8(5) . . . . ?
O1 C5 C6 C11 1.1(7) . . . . ?
C4 C5 C6 C7 5.2(8) . . . . ?
O1 C5 C6 C7 -175.0(5) . . . . ?
C11 C6 C7 C8 0.1(8) . . . . ?
C5 C6 C7 C8 176.3(5) . . . . ?
C6 C7 C8 C9 0.2(9) . . . . ?
C16 O7 C9 C10 0.5(8) . . . . ?
C16 O7 C9 C8 179.6(5) . . . . ?
C7 C8 C9 O7 -179.8(5) . . . . ?
C7 C8 C9 C10 -0.7(9) . . . . ?
O7 C9 C10 C11 179.9(5) . . . . ?
C8 C9 C10 C11 0.8(8) . . . . ?
C7 C6 C11 C10 0.1(8) . . . . ?
C5 C6 C11 C10 -176.0(5) . . . . ?
C9 C10 C11 C6 -0.6(8) . . . . ?
C13 O3 C12 O4 3.9(7) . . . . ?
C13 O3 C12 C2 -177.7(5) . . . . ?
C3 C2 C12 O4 -93.0(7) . . . . ?
C1 C2 C12 O4 83.0(6) . . . . ?
C3 C2 C12 O3 88.6(7) . . . . ?
C1 C2 C12 O3 -95.4(5) . . . . ?
C15 O5 C14 O6 2.9(8) . . . . ?
C15 O5 C14 C3 -177.0(4) . . . . ?
C2 C3 C14 O6 179.5(6) . . . . ?
C4 C3 C14 O6 0.5(8) . . . . ?
C2 C3 C14 O5 -0.5(7) . . . . ?
C4 C3 C14 O5 -179.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.124
