# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 O6'
_chemical_formula_weight         336.29

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.403(6)
_cell_length_b                   15.083(10)
_cell_length_c                   11.686(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.565(6)
_cell_angle_gamma                90.00
_cell_volume                     1464.6(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7660
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2550
_reflns_number_gt                2204
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0717P)²+0.2792P] 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         2550
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1270
_refine_ls_wR_factor_gt          0.1224
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_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
C1 C 0.94937(19) 0.23548(11) 0.42317(14) 0.0406(4) Uani 1 1 d . . .
H1A H 0.9547 0.2236 0.3423 0.049 Uiso 1 1 calc R . .
H1B H 1.0583 0.2464 0.4611 0.049 Uiso 1 1 calc R . .
C2 C 0.88754(18) 0.15388(11) 0.47545(14) 0.0390(4) Uani 1 1 d . . .
C3 C 0.94714(19) 0.13690(11) 0.59572(14) 0.0411(4) Uani 1 1 d . . .
C4 C 0.7823(2) 0.09727(11) 0.41554(14) 0.0408(4) Uani 1 1 d . . .
C5 C 0.73880(19) 0.01506(11) 0.46753(14) 0.0411(4) Uani 1 1 d . . .
C6 C 0.80323(19) 0.00006(11) 0.58171(15) 0.0413(4) Uani 1 1 d . . .
C7 C 0.7664(2) -0.07461(12) 0.64078(16) 0.0491(5) Uani 1 1 d . . .
H7A H 0.8108 -0.0835 0.7177 0.059 Uiso 1 1 calc R . .
C8 C 0.6622(2) -0.13559(12) 0.58284(18) 0.0548(5) Uani 1 1 d . . .
H8A H 0.6351 -0.1861 0.6213 0.066 Uiso 1 1 calc R . .
C9 C 0.5970(2) -0.12256(12) 0.46759(18) 0.0550(5) Uani 1 1 d . . .
H9A H 0.5271 -0.1643 0.4292 0.066 Uiso 1 1 calc R . .
C10 C 0.6359(2) -0.04801(12) 0.41068(17) 0.0498(5) Uani 1 1 d . . .
H10A H 0.5930 -0.0397 0.3334 0.060 Uiso 1 1 calc R . .
C11 C 0.85267(19) 0.31866(11) 0.43054(14) 0.0389(4) Uani 1 1 d . . .
C12 C 0.7284(2) 0.33687(11) 0.33437(14) 0.0409(4) Uani 1 1 d . . .
C13 C 0.87869(19) 0.37636(12) 0.52063(14) 0.0398(4) Uani 1 1 d . . .
C14 C 0.79602(19) 0.46018(11) 0.51582(14) 0.0392(4) Uani 1 1 d . . .
C15 C 0.68671(19) 0.47831(11) 0.41717(14) 0.0406(4) Uani 1 1 d . . .
C16 C 0.6034(2) 0.55699(12) 0.40297(16) 0.0481(4) Uani 1 1 d . . .
H16A H 0.5314 0.5681 0.3361 0.058 Uiso 1 1 calc R . .
C17 C 0.6294(2) 0.61874(12) 0.49001(18) 0.0529(5) Uani 1 1 d . . .
H17A H 0.5742 0.6724 0.4817 0.063 Uiso 1 1 calc R . .
C18 C 0.7361(2) 0.60265(12) 0.58973(17) 0.0507(5) Uani 1 1 d . . .
H18A H 0.7517 0.6452 0.6480 0.061 Uiso 1 1 calc R . .
C19 C 0.8186(2) 0.52444(12) 0.60293(15) 0.0459(4) Uani 1 1 d . . .
H19A H 0.8903 0.5139 0.6702 0.055 Uiso 1 1 calc R . .
O1 O 1.03307(14) 0.18764(9) 0.65914(11) 0.0527(4) Uani 1 1 d . . .
O2 O 0.90547(15) 0.06062(8) 0.64464(10) 0.0476(3) Uani 1 1 d . . .
O3 O 0.71250(16) 0.11155(9) 0.30716(11) 0.0519(4) Uani 1 1 d . . .
H3 H 0.698(3) 0.1700(18) 0.274(2) 0.078 Uiso 1 1 d . . .
O4 O 0.68461(16) 0.28537(9) 0.25573(11) 0.0548(4) Uani 1 1 d . . .
O5 O 0.65305(14) 0.41651(8) 0.32922(10) 0.0463(3) Uani 1 1 d . . .
O6 O 0.98204(14) 0.36093(9) 0.61637(10) 0.0498(3) Uani 1 1 d . . .
H6 H 1.022(3) 0.2972(16) 0.6326(19) 0.075 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
C1 C2 1.501(3) . ?
C1 C11 1.504(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C4 1.348(2) . ?
C2 C3 1.443(2) . ?
C3 O1 1.224(2) . ?
C3 O2 1.354(2) . ?
C4 O3 1.332(2) . ?
C4 C5 1.451(3) . ?
C5 C6 1.382(3) . ?
C5 C10 1.387(3) . ?
C6 C7 1.380(3) . ?
C6 O2 1.387(2) . ?
C7 C8 1.376(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.390(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.370(3) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 C13 1.358(2) . ?
C11 C12 1.442(2) . ?
C12 O4 1.218(2) . ?
C12 O5 1.355(2) . ?
C13 O6 1.331(2) . ?
C13 C14 1.440(3) . ?
C14 C15 1.390(2) . ?
C14 C19 1.398(3) . ?
C15 C16 1.375(3) . ?
C15 O5 1.385(2) . ?
C16 C17 1.372(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.382(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.366(3) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
O3 H3 0.96(3) . ?
O6 H6 1.03(2) . ?

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 C11 115.98(14) . . ?
C2 C1 H1A 108.3 . . ?
C11 C1 H1A 108.3 . . ?
C2 C1 H1B 108.3 . . ?
C11 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
C4 C2 C3 119.94(16) . . ?
C4 C2 C1 123.24(15) . . ?
C3 C2 C1 116.81(15) . . ?
O1 C3 O2 116.25(16) . . ?
O1 C3 C2 124.53(17) . . ?
O2 C3 C2 119.22(15) . . ?
O3 C4 C2 123.61(16) . . ?
O3 C4 C5 115.71(15) . . ?
C2 C4 C5 120.68(16) . . ?
C6 C5 C10 118.49(17) . . ?
C6 C5 C4 117.21(16) . . ?
C10 C5 C4 124.29(16) . . ?
C7 C6 C5 122.13(17) . . ?
C7 C6 O2 116.07(16) . . ?
C5 C6 O2 121.78(16) . . ?
C8 C7 C6 118.23(17) . . ?
C8 C7 H7A 120.9 . . ?
C6 C7 H7A 120.9 . . ?
C7 C8 C9 120.80(18) . . ?
C7 C8 H8A 119.6 . . ?
C9 C8 H8A 119.6 . . ?
C10 C9 C8 119.87(18) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C9 C10 C5 120.47(18) . . ?
C9 C10 H10A 119.8 . . ?
C5 C10 H10A 119.8 . . ?
C13 C11 C12 119.75(16) . . ?
C13 C11 C1 123.56(15) . . ?
C12 C11 C1 116.68(14) . . ?
O4 C12 O5 116.46(15) . . ?
O4 C12 C11 124.67(16) . . ?
O5 C12 C11 118.87(15) . . ?
O6 C13 C11 123.31(16) . . ?
O6 C13 C14 115.92(15) . . ?
C11 C13 C14 120.76(15) . . ?
C15 C14 C19 117.97(16) . . ?
C15 C14 C13 117.42(15) . . ?
C19 C14 C13 124.61(16) . . ?
C16 C15 O5 116.56(15) . . ?
C16 C15 C14 122.10(16) . . ?
O5 C15 C14 121.32(16) . . ?
C17 C16 C15 118.32(17) . . ?
C17 C16 H16A 120.8 . . ?
C15 C16 H16A 120.8 . . ?
C16 C17 C18 121.15(18) . . ?
C16 C17 H17A 119.4 . . ?
C18 C17 H17A 119.4 . . ?
C19 C18 C17 120.13(18) . . ?
C19 C18 H18A 119.9 . . ?
C17 C18 H18A 119.9 . . ?
C18 C19 C14 120.33(17) . . ?
C18 C19 H19A 119.8 . . ?
C14 C19 H19A 119.8 . . ?
C3 O2 C6 120.95(14) . . ?
C4 O3 H3 122.7(14) . . ?
C12 O5 C15 121.41(13) . . ?
C13 O6 H6 118.3(13) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.099
_database_code_depnum_ccdc_archive 'CCDC 989415'
