# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1406654'
_audit_update_record             
;
2015-06-15 deposited with the CCDC.
2015-12-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 O5'
_chemical_formula_weight         336.33

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                   7.1154(3)
_cell_length_b                   11.1585(5)
_cell_length_c                   11.1645(5)
_cell_angle_alpha                107.811(3)
_cell_angle_beta                 95.510(3)
_cell_angle_gamma                91.238(3)
_cell_volume                     838.83(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9811
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            7163
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2955
_reflns_number_gt                2328
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0760P)²+0.0918P] 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         2955
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1331
_refine_ls_wR_factor_gt          0.1210
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.24369(15) 0.90684(10) 0.84509(10) 0.0476(3) Uani 1 1 d . . .
O5 O 0.38390(17) 0.64601(13) 1.07359(12) 0.0637(4) Uani 1 1 d . . .
C7 C 0.2516(2) 1.03637(14) 0.87951(16) 0.0431(4) Uani 1 1 d . . .
O3 O 0.2466(2) 0.92359(13) 0.61458(12) 0.0745(4) Uani 1 1 d . . .
C11 C 0.2422(2) 0.86778(15) 0.95205(15) 0.0436(4) Uani 1 1 d . . .
C5 C 0.24898(19) 0.98080(15) 1.06154(15) 0.0443(4) Uani 1 1 d . . .
C12 C 0.2321(2) 0.74309(15) 0.93659(16) 0.0456(4) Uani 1 1 d . . .
C6 C 0.2525(2) 1.08392(15) 1.01585(15) 0.0442(4) Uani 1 1 d . . .
C8 C 0.2583(2) 1.09895(17) 0.79502(17) 0.0521(4) Uani 1 1 d . . .
H8A H 0.2629 1.1864 0.8281 0.063 Uiso 1 1 calc R . .
C15 C 0.2172(2) 0.63970(15) 0.81529(17) 0.0478(4) Uani 1 1 d . . .
O4 O 0.1020(2) 0.71513(17) 1.11684(17) 0.0983(6) Uani 1 1 d . . .
C13 C 0.2293(2) 0.70295(15) 1.05225(17) 0.0514(4) Uani 1 1 d . . .
O2 O 0.2726(3) 1.11316(16) 0.59071(15) 0.1018(6) Uani 1 1 d . . .
C1 C 0.2532(2) 1.20679(17) 1.09567(17) 0.0568(5) Uani 1 1 d . . .
H1A H 0.2554 1.2750 1.0643 0.068 Uiso 1 1 calc R . .
C4 C 0.2487(2) 1.00065(19) 1.19087(17) 0.0579(5) Uani 1 1 d . . .
H4A H 0.2484 0.9331 1.2231 0.069 Uiso 1 1 calc R . .
C9 C 0.2594(3) 1.04903(18) 0.65888(18) 0.0582(5) Uani 1 1 d . . .
C16 C 0.1351(2) 0.52294(17) 0.80997(19) 0.0574(5) Uani 1 1 d . . .
H16A H 0.0902 0.5131 0.8821 0.069 Uiso 1 1 calc R . .
C17 C 0.1190(3) 0.42241(19) 0.7007(2) 0.0694(6) Uani 1 1 d . . .
H17A H 0.0635 0.3458 0.6996 0.083 Uiso 1 1 calc R . .
C20 C 0.2814(3) 0.65062(18) 0.70512(18) 0.0619(5) Uani 1 1 d . . .
H20A H 0.3353 0.7272 0.7047 0.074 Uiso 1 1 calc R . .
C2 C 0.2506(3) 1.2241(2) 1.22291(19) 0.0677(6) Uani 1 1 d . . .
H2A H 0.2499 1.3055 1.2784 0.081 Uiso 1 1 calc R . .
C14 C 0.3930(3) 0.5958(2) 1.1791(2) 0.0821(7) Uani 1 1 d . . .
H14A H 0.5104 0.5561 1.1847 0.123 Uiso 1 1 calc R . .
H14B H 0.2897 0.5349 1.1664 0.123 Uiso 1 1 calc R . .
H14C H 0.3849 0.6631 1.2560 0.123 Uiso 1 1 calc R . .
C3 C 0.2489(3) 1.1227(2) 1.26994(19) 0.0673(5) Uani 1 1 d . . .
H3A H 0.2478 1.1373 1.3565 0.081 Uiso 1 1 calc R . .
C18 C 0.1843(3) 0.4348(2) 0.5942(2) 0.0783(6) Uani 1 1 d . . .
H18A H 0.1739 0.3667 0.5204 0.094 Uiso 1 1 calc R . .
C19 C 0.2657(3) 0.5483(2) 0.5961(2) 0.0771(6) Uani 1 1 d . . .
H19A H 0.3108 0.5565 0.5233 0.092 Uiso 1 1 calc R . .
C10 C 0.2471(4) 0.8671(2) 0.4803(2) 0.0927(8) Uani 1 1 d . . .
H10A H 0.2398 0.7770 0.4600 0.139 Uiso 1 1 calc R . .
H10B H 0.3617 0.8934 0.4543 0.139 Uiso 1 1 calc R . .
H10C H 0.1404 0.8932 0.4369 0.139 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 C7 1.3757(18) . ?
O1 C11 1.3916(19) . ?
O5 C13 1.320(2) . ?
O5 C14 1.447(2) . ?
C7 C8 1.338(2) . ?
C7 C6 1.450(2) . ?
O3 C9 1.332(2) . ?
O3 C10 1.438(3) . ?
C11 C12 1.348(2) . ?
C11 C5 1.459(2) . ?
C5 C4 1.392(2) . ?
C5 C6 1.395(2) . ?
C12 C15 1.479(2) . ?
C12 C13 1.492(2) . ?
C6 C1 1.388(2) . ?
C8 C9 1.451(3) . ?
C15 C20 1.390(3) . ?
C15 C16 1.399(2) . ?
O4 C13 1.196(2) . ?
O2 C9 1.202(2) . ?
C1 C2 1.376(3) . ?
C4 C3 1.378(3) . ?
C16 C17 1.375(3) . ?
C17 C18 1.361(3) . ?
C20 C19 1.384(3) . ?
C2 C3 1.386(3) . ?
C18 C19 1.375(3) . ?

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
C7 O1 C11 109.96(12) . . ?
C13 O5 C14 116.93(14) . . ?
C8 C7 O1 122.37(15) . . ?
C8 C7 C6 129.89(15) . . ?
O1 C7 C6 107.73(13) . . ?
C9 O3 C10 117.08(17) . . ?
C12 C11 O1 118.44(15) . . ?
C12 C11 C5 134.12(15) . . ?
O1 C11 C5 107.43(13) . . ?
C4 C5 C6 119.59(16) . . ?
C4 C5 C11 133.47(16) . . ?
C6 C5 C11 106.93(14) . . ?
C11 C12 C15 126.75(16) . . ?
C11 C12 C13 117.70(15) . . ?
C15 C12 C13 115.52(14) . . ?
C1 C6 C5 121.83(16) . . ?
C1 C6 C7 130.23(16) . . ?
C5 C6 C7 107.93(14) . . ?
C7 C8 C9 128.84(17) . . ?
C20 C15 C16 117.33(17) . . ?
C20 C15 C12 124.06(16) . . ?
C16 C15 C12 118.61(16) . . ?
O4 C13 O5 122.65(17) . . ?
O4 C13 C12 125.60(16) . . ?
O5 C13 C12 111.68(13) . . ?
C2 C1 C6 117.57(18) . . ?
C3 C4 C5 118.50(18) . . ?
O2 C9 O3 122.04(19) . . ?
O2 C9 C8 124.09(19) . . ?
O3 C9 C8 113.86(16) . . ?
C17 C16 C15 121.62(19) . . ?
C18 C17 C16 120.10(19) . . ?
C19 C20 C15 120.44(19) . . ?
C1 C2 C3 121.29(19) . . ?
C4 C3 C2 121.21(19) . . ?
C17 C18 C19 119.8(2) . . ?
C18 C19 C20 120.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.123
