# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 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_hxf
_database_code_depnum_ccdc_archive 'CCDC 1555431'
_audit_update_record             
;
2017-06-12 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 O6'
_chemical_formula_weight         278.25

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                   10.7247(11)
_cell_length_b                   7.7401(8)
_cell_length_c                   14.5763(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.544(2)
_cell_angle_gamma                90.00
_cell_volume                     1181.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    185(2)
_cell_measurement_reflns_used    1086
_cell_measurement_theta_min      2.8632
_cell_measurement_theta_max      21.0290

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9569
_exptl_absorpt_correction_T_max  0.9698
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      185(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 APEX CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7106
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         26.04
_reflns_number_total             2319
_reflns_number_gt                1405
_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)+(0.1556P)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         2319
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.2413
_refine_ls_wR_factor_gt          0.1661
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.048
_refine_ls_shift/su_mean         0.009

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
O2 O 0.9998(2) 0.0385(3) 0.37067(16) 0.0559(7) Uani 1 1 d . . .
C5 C 0.6808(3) 0.0607(4) 0.37784(19) 0.0377(7) Uani 1 1 d . . .
H5A H 0.5916 0.1064 0.3672 0.045 Uiso 1 1 calc R . .
O5 O 0.6104(2) -0.1293(4) 0.51928(19) 0.0645(8) Uani 1 1 d . . .
C6 C 0.7448(3) 0.1437(4) 0.30311(19) 0.0378(7) Uani 1 1 d . . .
H6A H 0.6761 0.2040 0.2569 0.045 Uiso 1 1 calc R . .
O3 O 0.9583(3) -0.2128(3) 0.3028(2) 0.0725(8) Uani 1 1 d . . .
O1 O 1.0552(2) 0.2814(4) 0.4419(2) 0.0860(10) Uani 1 1 d . . .
C12 C 0.9220(3) -0.0683(5) 0.3071(2) 0.0482(8) Uani 1 1 d . . .
C1 C 0.8443(3) 0.2795(4) 0.3445(2) 0.0457(8) Uani 1 1 d . . .
H1A H 0.8568 0.3540 0.2912 0.055 Uiso 1 1 calc R . .
C7 C 0.8042(3) 0.0100(4) 0.2483(2) 0.0458(8) Uani 1 1 d . . .
H7A H 0.8312 0.0735 0.1962 0.055 Uiso 1 1 calc R . .
O6 O 0.5328(3) -0.3350(4) 0.4201(3) 0.0897(11) Uani 1 1 d . . .
C10 C 0.6721(3) -0.1346(4) 0.3676(2) 0.0452(8) Uani 1 1 d . . .
H10A H 0.7611 -0.1804 0.3866 0.054 Uiso 1 1 calc R . .
O4 O 0.6877(3) 0.0662(4) 0.62521(18) 0.0873(10) Uani 1 1 d . . .
C4 C 0.7467(3) 0.1047(4) 0.4777(2) 0.0461(8) Uani 1 1 d . . .
H4A H 0.8345 0.0543 0.4878 0.055 Uiso 1 1 calc R . .
C13 C 0.6824(4) 0.0173(5) 0.5468(2) 0.0597(10) Uani 1 1 d . . .
C11 C 0.9717(3) 0.2078(5) 0.3894(2) 0.0523(9) Uani 1 1 d . . .
C14 C 0.5986(3) -0.2101(5) 0.4330(3) 0.0579(10) Uani 1 1 d . . .
C2 C 0.7913(4) 0.3963(5) 0.4122(3) 0.0598(10) Uani 1 1 d . . .
H2A H 0.8537 0.4893 0.4350 0.072 Uiso 1 1 calc R . .
H2B H 0.7114 0.4511 0.3777 0.072 Uiso 1 1 calc R . .
C9 C 0.6216(4) -0.1877(5) 0.2666(3) 0.0614(10) Uani 1 1 d . . .
H9A H 0.5354 -0.1377 0.2439 0.074 Uiso 1 1 calc R . .
H9B H 0.6137 -0.3150 0.2630 0.074 Uiso 1 1 calc R . .
C8 C 0.7097(4) -0.1269(5) 0.2028(2) 0.0610(10) Uani 1 1 d . . .
H8A H 0.7574 -0.2275 0.1862 0.073 Uiso 1 1 calc R . .
H8B H 0.6569 -0.0799 0.1439 0.073 Uiso 1 1 calc R . .
C3 C 0.7640(4) 0.2978(5) 0.4964(3) 0.0627(10) Uani 1 1 d . . .
H3A H 0.8356 0.3160 0.5511 0.075 Uiso 1 1 calc R . .
H3B H 0.6857 0.3450 0.5124 0.075 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
O2 C12 1.379(4) . ?
O2 C11 1.385(4) . ?
C5 C4 1.513(4) . ?
C5 C10 1.519(4) . ?
C5 C6 1.548(4) . ?
C5 H5A 1.0000 . ?
O5 C13 1.382(5) . ?
O5 C14 1.386(5) . ?
C6 C1 1.525(4) . ?
C6 C7 1.528(4) . ?
C6 H6A 1.0000 . ?
O3 C12 1.190(4) . ?
O1 C11 1.188(4) . ?
C12 C7 1.493(4) . ?
C1 C11 1.489(5) . ?
C1 C2 1.536(5) . ?
C1 H1A 1.0000 . ?
C7 C8 1.515(5) . ?
C7 H7A 1.0000 . ?
O6 C14 1.188(4) . ?
C10 C14 1.482(5) . ?
C10 C9 1.512(5) . ?
C10 H10A 1.0000 . ?
O4 C13 1.193(4) . ?
C4 C13 1.500(5) . ?
C4 C3 1.524(5) . ?
C4 H4A 1.0000 . ?
C2 C3 1.526(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C9 C8 1.536(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?

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
C12 O2 C11 125.0(3) . . ?
C4 C5 C10 108.9(3) . . ?
C4 C5 C6 113.4(2) . . ?
C10 C5 C6 111.8(2) . . ?
C4 C5 H5A 107.5 . . ?
C10 C5 H5A 107.5 . . ?
C6 C5 H5A 107.5 . . ?
C13 O5 C14 124.7(3) . . ?
C1 C6 C7 109.8(2) . . ?
C1 C6 C5 112.8(2) . . ?
C7 C6 C5 112.7(3) . . ?
C1 C6 H6A 107.1 . . ?
C7 C6 H6A 107.1 . . ?
C5 C6 H6A 107.1 . . ?
O3 C12 O2 116.2(3) . . ?
O3 C12 C7 126.6(3) . . ?
O2 C12 C7 117.1(3) . . ?
C11 C1 C6 114.4(3) . . ?
C11 C1 C2 111.7(3) . . ?
C6 C1 C2 109.6(3) . . ?
C11 C1 H1A 106.9 . . ?
C6 C1 H1A 106.9 . . ?
C2 C1 H1A 106.9 . . ?
C12 C7 C8 111.7(3) . . ?
C12 C7 C6 111.8(2) . . ?
C8 C7 C6 112.8(3) . . ?
C12 C7 H7A 106.7 . . ?
C8 C7 H7A 106.7 . . ?
C6 C7 H7A 106.7 . . ?
C14 C10 C9 113.0(3) . . ?
C14 C10 C5 111.0(3) . . ?
C9 C10 C5 111.5(3) . . ?
C14 C10 H10A 107.0 . . ?
C9 C10 H10A 107.0 . . ?
C5 C10 H10A 107.0 . . ?
C13 C4 C5 111.0(3) . . ?
C13 C4 C3 112.2(3) . . ?
C5 C4 C3 113.9(3) . . ?
C13 C4 H4A 106.4 . . ?
C5 C4 H4A 106.4 . . ?
C3 C4 H4A 106.4 . . ?
O4 C13 O5 116.5(4) . . ?
O4 C13 C4 124.6(4) . . ?
O5 C13 C4 119.0(3) . . ?
O1 C11 O2 114.5(3) . . ?
O1 C11 C1 126.6(3) . . ?
O2 C11 C1 118.9(3) . . ?
O6 C14 O5 116.4(3) . . ?
O6 C14 C10 126.9(4) . . ?
O5 C14 C10 116.7(3) . . ?
C3 C2 C1 112.7(3) . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C10 C9 C8 111.6(3) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C7 C8 C9 113.0(3) . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C4 C3 C2 112.6(3) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.04
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.167
