# 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_GC
_database_code_depnum_ccdc_archive 'CCDC 1514598'
_audit_update_record             
;
2016-11-03 deposited with the CCDC.
2017-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 O11'
_chemical_formula_weight         374.29

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   'C 2'

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

_cell_length_a                   28.835(8)
_cell_length_b                   6.5931(18)
_cell_length_c                   9.909(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.373(6)
_cell_angle_gamma                90.00
_cell_volume                     1816.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2353
_cell_measurement_theta_min      2.2437
_cell_measurement_theta_max      24.9777

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9882
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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 SMART APEX II 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            4785
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3066
_reflns_number_gt                2615
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2  (Bruker, 2008)'
_computing_cell_refinement       'SAINT+ ver. (Bruker, 2001)'
_computing_data_reduction        'SAINT+ ver. (Bruker, 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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 > 2σ(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)+(0.0872P)²+1.1860P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0110(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(16)
_refine_ls_number_reflns         3066
_refine_ls_number_parameters     224
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1586
_refine_ls_wR_factor_gt          0.1502
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
O2 O 0.78179(9) 1.1893(4) 0.5079(3) 0.0691(7) Uani 1 1 d . . .
O4 O 0.71999(9) 1.1083(5) 0.3346(3) 0.0771(8) Uani 1 1 d . . .
O3 O 0.78636(7) 0.9382(3) 0.3497(2) 0.0522(6) Uani 1 1 d . . .
O5 O 0.89511(9) 0.5935(4) 0.6803(3) 0.0629(7) Uani 1 1 d . . .
O6 O 0.91895(9) 0.4796(4) 0.4451(3) 0.0665(7) Uani 1 1 d . . .
O7 O 0.96838(16) 0.5716(10) 0.3184(5) 0.1368(14) Uani 1 1 d . . .
O8 O 0.95499(13) 0.2492(7) 0.3600(5) 0.1138(14) Uani 1 1 d . . .
O9 O 0.84528(8) 0.6736(3) 0.2406(2) 0.0529(6) Uani 1 1 d . . .
O10 O 0.80658(12) 0.3781(5) 0.2457(3) 0.0789(9) Uani 1 1 d . . .
O11 O 0.81718(10) 0.5147(4) 0.0483(3) 0.0693(8) Uani 1 1 d . . .
C6 C 0.83157(14) 1.1671(6) 0.5875(4) 0.0628(9) Uani 1 1 d . . .
H6A H 0.8346 1.1918 0.6880 0.075 Uiso 1 1 calc R . .
H6B H 0.8519 1.2670 0.5551 0.075 Uiso 1 1 calc R . .
C15 C 0.76124(12) 1.0826(6) 0.3950(4) 0.0566(9) Uani 1 1 d . . .
C4 C 0.83698(10) 0.9173(5) 0.4127(3) 0.0433(7) Uani 1 1 d . . .
H4 H 0.8550 1.0169 0.3697 0.052 Uiso 1 1 calc R . .
C5 C 0.84778(11) 0.9548(5) 0.5667(3) 0.0471(7) Uani 1 1 d . . .
H5 H 0.8303 0.8544 0.6108 0.057 Uiso 1 1 calc R . .
O1 O 0.89854(8) 0.9393(4) 0.6283(3) 0.0574(6) Uani 1 1 d . . .
C1 C 0.91572(12) 0.7405(6) 0.6145(4) 0.0586(9) Uani 1 1 d . . .
H1 H 0.9514 0.7384 0.6557 0.070 Uiso 1 1 calc R . .
C2 C 0.90505(12) 0.6859(5) 0.4599(4) 0.0554(9) Uani 1 1 d . . .
H2 H 0.9237 0.7779 0.4135 0.067 Uiso 1 1 calc R . .
C3 C 0.85182(10) 0.7054(5) 0.3872(3) 0.0443(7) Uani 1 1 d . . .
H3 H 0.8328 0.6040 0.4254 0.053 Uiso 1 1 calc R . .
C7 C 0.9100(2) 0.5998(10) 0.8272(5) 0.1004(16) Uani 1 1 d . . .
H7A H 0.8937 0.4923 0.8655 0.151 Uiso 1 1 calc R . .
H7B H 0.9017 0.7320 0.8598 0.151 Uiso 1 1 calc R . .
H7C H 0.9449 0.5796 0.8589 0.151 Uiso 1 1 calc R . .
C8 C 0.94923(14) 0.4439(8) 0.3690(5) 0.0764(12) Uani 1 1 d . . .
C9 C 0.9889(2) 0.1759(14) 0.2900(8) 0.1368(14) Uani 1 1 d . . .
H9A H 1.0111 0.2876 0.2829 0.164 Uiso 1 1 calc R . .
H9B H 1.0082 0.0670 0.3472 0.164 Uiso 1 1 calc R . .
C10 C 0.9691(2) 0.1048(14) 0.1635(8) 0.1368(14) Uani 1 1 d . . .
H10A H 0.9944 0.0603 0.1208 0.205 Uiso 1 1 calc R . .
H10B H 0.9499 0.2116 0.1059 0.205 Uiso 1 1 calc R . .
H10C H 0.9483 -0.0105 0.1698 0.205 Uiso 1 1 calc R . .
C11 C 0.82099(12) 0.5072(5) 0.1854(4) 0.0518(8) Uani 1 1 d . . .
C12 C 0.78814(18) 0.3573(8) -0.0342(5) 0.0833(13) Uani 1 1 d . . .
H12A H 0.7777 0.4021 -0.1330 0.100 Uiso 1 1 calc R . .
H12B H 0.7590 0.3372 -0.0010 0.100 Uiso 1 1 calc R . .
C13 C 0.8131(2) 0.1662(8) -0.0273(5) 0.0808(12) Uani 1 1 d . . .
C14 C 0.8299(3) 0.0111(11) -0.0270(8) 0.134(3) Uani 1 1 d . . .
H14 H 0.8439 -0.1192 -0.0268 0.161 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C15 1.321(5) . ?
O2 C6 1.451(5) . ?
O4 C15 1.193(4) . ?
O3 C15 1.344(4) . ?
O3 C4 1.434(3) . ?
O5 C1 1.387(5) . ?
O5 C7 1.405(5) . ?
O6 C8 1.317(5) . ?
O6 C2 1.436(4) . ?
O7 C8 1.188(7) . ?
O8 C8 1.301(7) . ?
O8 C9 1.424(6) . ?
O9 C11 1.338(4) . ?
O9 C3 1.430(4) . ?
O10 C11 1.177(4) . ?
O11 C11 1.334(4) . ?
O11 C12 1.443(5) . ?
C6 C5 1.508(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C4 C5 1.495(4) . ?
C4 C3 1.502(4) . ?
C4 H4 1.0000 . ?
C5 O1 1.432(4) . ?
C5 H5 1.0000 . ?
O1 C1 1.421(5) . ?
C1 C2 1.523(5) . ?
C1 H1 1.0000 . ?
C2 C3 1.519(4) . ?
C2 H2 1.0000 . ?
C3 H3 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 C10 1.318(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 C13 1.444(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.131(8) . ?
C14 H14 0.9500 . ?

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
C15 O2 C6 124.3(3) . . ?
C15 O3 C4 120.0(3) . . ?
C1 O5 C7 114.6(4) . . ?
C8 O6 C2 118.2(4) . . ?
C8 O8 C9 119.0(6) . . ?
C11 O9 C3 116.7(2) . . ?
C11 O11 C12 115.4(3) . . ?
O2 C6 C5 108.5(3) . . ?
O2 C6 H6A 110.0 . . ?
C5 C6 H6A 110.0 . . ?
O2 C6 H6B 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
O4 C15 O2 120.8(3) . . ?
O4 C15 O3 119.1(4) . . ?
O2 C15 O3 120.0(3) . . ?
O3 C4 C5 109.9(2) . . ?
O3 C4 C3 108.6(2) . . ?
C5 C4 C3 109.5(3) . . ?
O3 C4 H4 109.6 . . ?
C5 C4 H4 109.6 . . ?
C3 C4 H4 109.6 . . ?
O1 C5 C4 109.6(2) . . ?
O1 C5 C6 109.1(3) . . ?
C4 C5 C6 107.7(3) . . ?
O1 C5 H5 110.1 . . ?
C4 C5 H5 110.1 . . ?
C6 C5 H5 110.1 . . ?
C1 O1 C5 111.6(2) . . ?
O5 C1 O1 113.3(3) . . ?
O5 C1 C2 108.1(3) . . ?
O1 C1 C2 109.4(3) . . ?
O5 C1 H1 108.7 . . ?
O1 C1 H1 108.7 . . ?
C2 C1 H1 108.7 . . ?
O6 C2 C3 107.8(3) . . ?
O6 C2 C1 109.8(3) . . ?
C3 C2 C1 111.5(2) . . ?
O6 C2 H2 109.2 . . ?
C3 C2 H2 109.2 . . ?
C1 C2 H2 109.2 . . ?
O9 C3 C4 109.9(3) . . ?
O9 C3 C2 108.3(2) . . ?
C4 C3 C2 107.2(2) . . ?
O9 C3 H3 110.4 . . ?
C4 C3 H3 110.4 . . ?
C2 C3 H3 110.4 . . ?
O5 C7 H7A 109.5 . . ?
O5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O7 C8 O8 126.0(5) . . ?
O7 C8 O6 124.6(5) . . ?
O8 C8 O6 109.4(5) . . ?
C10 C9 O8 113.9(6) . . ?
C10 C9 H9A 108.8 . . ?
O8 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
O8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O10 C11 O11 126.7(3) . . ?
O10 C11 O9 127.1(3) . . ?
O11 C11 O9 106.2(3) . . ?
O11 C12 C13 113.2(4) . . ?
O11 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
O11 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 175.4(7) . . ?
C13 C14 H14 180.0 . . ?

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
C15 O2 C6 C5 -26.1(5) . . . . ?
C6 O2 C15 O4 179.8(3) . . . . ?
C6 O2 C15 O3 2.1(6) . . . . ?
C4 O3 C15 O4 174.3(3) . . . . ?
C4 O3 C15 O2 -8.0(5) . . . . ?
C15 O3 C4 C5 37.8(4) . . . . ?
C15 O3 C4 C3 157.6(3) . . . . ?
O3 C4 C5 O1 -178.4(2) . . . . ?
C3 C4 C5 O1 62.4(3) . . . . ?
O3 C4 C5 C6 -59.8(3) . . . . ?
C3 C4 C5 C6 -179.0(3) . . . . ?
O2 C6 C5 O1 171.9(3) . . . . ?
O2 C6 C5 C4 53.0(3) . . . . ?
C4 C5 O1 C1 -63.5(3) . . . . ?
C6 C5 O1 C1 178.7(3) . . . . ?
C7 O5 C1 O1 -70.9(4) . . . . ?
C7 O5 C1 C2 167.7(4) . . . . ?
C5 O1 C1 O5 -61.1(4) . . . . ?
C5 O1 C1 C2 59.5(3) . . . . ?
C8 O6 C2 C3 113.8(4) . . . . ?
C8 O6 C2 C1 -124.5(4) . . . . ?
O5 C1 C2 O6 -51.8(3) . . . . ?
O1 C1 C2 O6 -175.6(2) . . . . ?
O5 C1 C2 C3 67.6(4) . . . . ?
O1 C1 C2 C3 -56.1(4) . . . . ?
C11 O9 C3 C4 -129.7(3) . . . . ?
C11 O9 C3 C2 113.4(3) . . . . ?
O3 C4 C3 O9 64.7(3) . . . . ?
C5 C4 C3 O9 -175.3(2) . . . . ?
O3 C4 C3 C2 -177.8(2) . . . . ?
C5 C4 C3 C2 -57.8(3) . . . . ?
O6 C2 C3 O9 -65.6(3) . . . . ?
C1 C2 C3 O9 173.8(3) . . . . ?
O6 C2 C3 C4 175.8(3) . . . . ?
C1 C2 C3 C4 55.2(3) . . . . ?
C9 O8 C8 O7 3.5(9) . . . . ?
C9 O8 C8 O6 -175.8(5) . . . . ?
C2 O6 C8 O7 5.0(7) . . . . ?
C2 O6 C8 O8 -175.8(4) . . . . ?
C8 O8 C9 C10 -103.7(8) . . . . ?
C12 O11 C11 O10 6.6(5) . . . . ?
C12 O11 C11 O9 -174.6(3) . . . . ?
C3 O9 C11 O10 -4.4(5) . . . . ?
C3 O9 C11 O11 176.8(3) . . . . ?
C11 O11 C12 C13 -79.3(5) . . . . ?
O11 C12 C13 C14 175(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.042
