# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1575963'
_audit_update_record             
;
2018-01-21 deposited with the CCDC.
2018-03-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H10 O7'
_chemical_formula_iupac          ?
_chemical_formula_weight         218.16

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.5437(12)
_cell_length_b                   8.0245(9)
_cell_length_c                   10.8487(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.598(2)
_cell_angle_gamma                90
_cell_volume                     916.08(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8594
_cell_measurement_theta_min      4.0830
_cell_measurement_theta_max      68.3049
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.281
_exptl_crystal_size_min          0.199
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456

_exptl_absorpt_coefficient_mu    1.246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_T_max  0.79

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'INCOATEC I\mS micro--focus source'
_diffrn_source_type              ?

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  mirror

_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            10146
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_theta_min         6.87
_diffrn_reflns_theta_max         67.46
_diffrn_reflns_theta_full        67.46
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
;

_reflns_number_total             1641
_reflns_number_gt                1603
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0851
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_restrained_S_all      1.195
_refine_ls_number_reflns         1641
_refine_ls_number_parameters     194
_refine_ls_number_restraints     49
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0331P)²+0.4109P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.182
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0151(9)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 V2013 (Bruker AXS Inc., 2013)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 V2013 (Bruker AXS Inc., 2013)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.3166(4) 0.1095(11) 0.4150(7) 0.0273(9) Uani d . P D 0.839(3) A 1
O O2 0.5206(3) 0.1253(4) 0.3678(3) 0.0359(6) Uani d . P D 0.839(3) A 1
O O3 0.45621(17) 0.2461(3) 0.53796(19) 0.0277(4) Uani d . P D 0.839(3) A 1
O O4 0.27576(14) 0.49926(18) 0.46997(11) 0.0240(4) Uani d . P D 0.839(3) A 1
O O5 0.1660(3) 0.6258(5) 0.2373(3) 0.0265(8) Uani d . P D 0.839(3) A 1
O O6 -0.0177(3) 0.5056(5) 0.2035(3) 0.0365(7) Uani d . P D 0.839(3) A 1
O O7 0.0200(3) 0.6160(5) 0.3869(3) 0.0255(7) Uani d . P D 0.839(3) A 1
C C1 0.43737(14) 0.15636(19) 0.43451(14) 0.0266(4) Uani d . P D 0.839(3) A 1
C C2 0.33602(19) 0.2685(2) 0.59595(16) 0.0257(5) Uani d . P D 0.839(3) A 1
H H2 0.3431 0.2249 0.6825 0.031 Uiso calc U P R 0.839(3) A 1
C C3 0.2429(5) 0.1605(6) 0.5148(5) 0.0286(9) Uani d U P D 0.839(3) A 1
H H3A 0.2139 0.0629 0.5614 0.034 Uiso calc U P R 0.839(3) A 1
H H3B 0.1678 0.2261 0.4843 0.034 Uiso calc U P R 0.839(3) A 1
C C4 0.30161(17) 0.4503(2) 0.59556(15) 0.0242(4) Uani d . P D 0.839(3) A 1
H H4A 0.2258 0.4686 0.6432 0.029 Uiso calc U P R 0.839(3) A 1
H H4B 0.3728 0.5167 0.6338 0.029 Uiso calc U P R 0.839(3) A 1
C C5 0.24105(16) 0.6698(2) 0.45612(15) 0.0205(4) Uani d . P D 0.839(3) A 1
H H5 0.2973 0.7405 0.5123 0.025 Uiso calc U P R 0.839(3) A 1
C C6 0.2568(3) 0.7178(5) 0.3218(3) 0.0237(7) Uani d U P D 0.839(3) A 1
H H6A 0.2426 0.8391 0.3114 0.028 Uiso calc U P R 0.839(3) A 1
H H6B 0.3447 0.6929 0.3003 0.028 Uiso calc U P R 0.839(3) A 1
C C7 0.0518(6) 0.5825(11) 0.2742(5) 0.0254(15) Uani d . P D 0.839(3) A 1
C C8 0.10314(17) 0.7004(2) 0.47999(16) 0.0206(4) Uani d . P D 0.839(3) A 1
H H8A 0.0858 0.6586 0.5631 0.025 Uiso calc U P R 0.839(3) A 1
H H8B 0.0856 0.8216 0.4777 0.025 Uiso calc U P R 0.839(3) A 1
O O1B 0.1801(16) 0.645(2) 0.2479(17) 0.011(3) Uiso d . P D 0.161(3) A 2
O O2B -0.0254(19) 0.543(2) 0.199(2) 0.033(5) Uiso d . P D 0.161(3) A 2
O O3B 0.0372(17) 0.637(3) 0.3873(19) 0.026(5) Uiso d . P D 0.161(3) A 2
O O4B 0.2278(8) 0.4352(11) 0.4797(7) 0.031(2) Uiso d . P D 0.161(3) A 2
O O5B 0.318(3) 0.095(6) 0.428(4) 0.035(10) Uiso d . P D 0.161(3) A 2
O O6B 0.5042(18) 0.089(2) 0.3594(18) 0.040(5) Uiso d . P D 0.161(3) A 2
O O7B 0.4754(13) 0.2763(16) 0.5097(11) 0.042(4) Uiso d . P D 0.161(3) A 2
C C1B 0.066(3) 0.591(5) 0.269(3) 0.016(7) Uiso d . P D 0.161(3) A 2
C C2B 0.1583(11) 0.7038(12) 0.4396(9) 0.023(2) Uiso d . P D 0.161(3) A 2
H H2B 0.1451 0.8174 0.4745 0.028 Uiso calc U P R 0.161(3) A 2
C C3B 0.2560(19) 0.711(3) 0.3458(16) 0.026(4) Uiso d U P D 0.161(3) A 2
H H3B1 0.2837 0.8264 0.3295 0.032 Uiso calc U P R 0.161(3) A 2
H H3B2 0.3308 0.6402 0.3684 0.032 Uiso calc U P R 0.161(3) A 2
C C4B 0.2106(10) 0.5923(12) 0.5365(9) 0.032(3) Uiso d . P D 0.161(3) A 2
H H4B1 0.2928 0.6355 0.5723 0.038 Uiso calc U P R 0.161(3) A 2
H H4B2 0.1513 0.5822 0.6033 0.038 Uiso calc U P R 0.161(3) A 2
C C5B 0.2593(10) 0.3141(12) 0.5682(9) 0.028(2) Uiso d . P D 0.161(3) A 2
H H5B 0.2077 0.3348 0.6409 0.034 Uiso calc U P R 0.161(3) A 2
C C6B 0.236(2) 0.140(3) 0.526(2) 0.018(4) Uiso d U P D 0.161(3) A 2
H H6B1 0.2507 0.0633 0.5964 0.022 Uiso calc U P R 0.161(3) A 2
H H6B2 0.1456 0.129 0.4949 0.022 Uiso calc U P R 0.161(3) A 2
C C7B 0.43737(14) 0.15636(19) 0.43451(14) 0.0266(4) Uani d . P D 0.161(3) A 2
C C8B 0.3991(13) 0.3205(18) 0.6125(12) 0.047(3) Uiso d . P D 0.161(3) A 2
H H8B1 0.4216 0.4339 0.6423 0.057 Uiso calc U P R 0.161(3) A 2
H H8B2 0.4159 0.2413 0.6816 0.057 Uiso calc U P R 0.161(3) A 2


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.331(4) ?
O1 C3 . 1.433(5) ?
O2 C1 . 1.198(3) ?
O3 C1 . 1.338(2) ?
O3 C2 . 1.461(3) ?
O4 C5 . 1.422(2) ?
O4 C4 . 1.428(2) ?
O5 C7 . 1.337(6) ?
O5 C6 . 1.481(4) ?
O6 C7 . 1.198(5) ?
O7 C7 . 1.316(5) ?
O7 C8 . 1.461(4) ?
C2 C4 . 1.503(3) ?
C2 C3 . 1.543(6) ?
C2 H2 . 1.0 ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 C8 . 1.513(2) ?
C5 C6 . 1.527(3) ?
C5 H5 . 1.0 ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
O1B C1B . 1.31(2) ?
O1B C3B . 1.39(2) ?
O2B C1B . 1.25(2) ?
O3B C1B . 1.39(3) ?
O3B C2B . 1.464(18) ?
O4B C5B . 1.391(12) ?
O4B C4B . 1.420(12) ?
O5B C6B . 1.45(3) ?
O7B C8B . 1.459(15) ?
C2B C4B . 1.462(13) ?
C2B C3B . 1.49(2) ?
C2B H2B . 1.0 ?
C3B H3B1 . 0.99 ?
C3B H3B2 . 0.99 ?
C4B H4B1 . 0.99 ?
C4B H4B2 . 0.99 ?
C5B C6B . 1.48(2) ?
C5B C8B . 1.522(15) ?
C5B H5B . 1.0 ?
C6B H6B1 . 0.99 ?
C6B H6B2 . 0.99 ?
C8B H8B1 . 0.99 ?
C8B H8B2 . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C3 . . 111.0(4) ?
C1 O3 C2 . . 109.89(16) ?
C5 O4 C4 . . 113.48(13) ?
C7 O5 C6 . . 120.2(4) ?
C7 O7 C8 . . 124.0(4) ?
O2 C1 O1 . . 125.0(3) ?
O2 C1 O3 . . 122.9(2) ?
O1 C1 O3 . . 112.1(2) ?
O3 C2 C4 . . 109.49(16) ?
O3 C2 C3 . . 102.9(2) ?
C4 C2 C3 . . 113.5(2) ?
O3 C2 H2 . . 110.2 ?
C4 C2 H2 . . 110.2 ?
C3 C2 H2 . . 110.2 ?
O1 C3 C2 . . 103.6(3) ?
O1 C3 H3A . . 111.0 ?
C2 C3 H3A . . 111.0 ?
O1 C3 H3B . . 111.0 ?
C2 C3 H3B . . 111.0 ?
H3A C3 H3B . . 109.0 ?
O4 C4 C2 . . 107.55(14) ?
O4 C4 H4A . . 110.2 ?
C2 C4 H4A . . 110.2 ?
O4 C4 H4B . . 110.2 ?
C2 C4 H4B . . 110.2 ?
H4A C4 H4B . . 108.5 ?
O4 C5 C8 . . 112.47(14) ?
O4 C5 C6 . . 107.54(19) ?
C8 C5 C6 . . 106.59(19) ?
O4 C5 H5 . . 110.0 ?
C8 C5 H5 . . 110.0 ?
C6 C5 H5 . . 110.0 ?
O5 C6 C5 . . 111.1(3) ?
O5 C6 H6A . . 109.4 ?
C5 C6 H6A . . 109.4 ?
O5 C6 H6B . . 109.4 ?
C5 C6 H6B . . 109.4 ?
H6A C6 H6B . . 108.0 ?
O6 C7 O7 . . 121.2(5) ?
O6 C7 O5 . . 117.9(5) ?
O7 C7 O5 . . 120.8(4) ?
O7 C8 C5 . . 110.36(19) ?
O7 C8 H8A . . 109.6 ?
C5 C8 H8A . . 109.6 ?
O7 C8 H8B . . 109.6 ?
C5 C8 H8B . . 109.6 ?
H8A C8 H8B . . 108.1 ?
C1B O1B C3B . . 118.9(18) ?
C1B O3B C2B . . 102.6(15) ?
C5B O4B C4B . . 110.6(7) ?
O2B C1B O1B . . 133.(3) ?
O2B C1B O3B . . 116.(2) ?
O1B C1B O3B . . 109.2(19) ?
C4B C2B O3B . . 109.6(12) ?
C4B C2B C3B . . 105.6(12) ?
O3B C2B C3B . . 111.8(13) ?
C4B C2B H2B . . 109.9 ?
O3B C2B H2B . . 109.9 ?
C3B C2B H2B . . 109.9 ?
O1B C3B C2B . . 96.7(14) ?
O1B C3B H3B1 . . 112.4 ?
C2B C3B H3B1 . . 112.4 ?
O1B C3B H3B2 . . 112.4 ?
C2B C3B H3B2 . . 112.4 ?
H3B1 C3B H3B2 . . 110.0 ?
O4B C4B C2B . . 106.5(8) ?
O4B C4B H4B1 . . 110.4 ?
C2B C4B H4B1 . . 110.4 ?
O4B C4B H4B2 . . 110.4 ?
C2B C4B H4B2 . . 110.4 ?
H4B1 C4B H4B2 . . 108.6 ?
O4B C5B C6B . . 114.4(13) ?
O4B C5B C8B . . 112.3(9) ?
C6B C5B C8B . . 105.7(13) ?
O4B C5B H5B . . 108.1 ?
C6B C5B H5B . . 108.1 ?
C8B C5B H5B . . 108.1 ?
O5B C6B C5B . . 111.(2) ?
O5B C6B H6B1 . . 109.4 ?
C5B C6B H6B1 . . 109.4 ?
O5B C6B H6B2 . . 109.4 ?
C5B C6B H6B2 . . 109.4 ?
H6B1 C6B H6B2 . . 108.0 ?
O7B C8B C5B . . 108.6(11) ?
O7B C8B H8B1 . . 110.0 ?
C5B C8B H8B1 . . 110.0 ?
O7B C8B H8B2 . . 110.0 ?
C5B C8B H8B2 . . 110.0 ?
H8B1 C8B H8B2 . . 108.3 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 O1 C1 O2 . . . . 177.5(4) ?
C3 O1 C1 O3 . . . . -3.5(8) ?
C2 O3 C1 O2 . . . . 177.5(2) ?
C2 O3 C1 O1 . . . . -1.5(5) ?
C1 O3 C2 C4 . . . . -115.64(18) ?
C1 O3 C2 C3 . . . . 5.4(3) ?
C1 O1 C3 C2 . . . . 6.6(8) ?
O3 C2 C3 O1 . . . . -6.9(5) ?
C4 C2 C3 O1 . . . . 111.3(5) ?
C5 O4 C4 C2 . . . . 179.70(15) ?
O3 C2 C4 O4 . . . . 66.46(19) ?
C3 C2 C4 O4 . . . . -47.9(2) ?
C4 O4 C5 C8 . . . . -80.30(18) ?
C4 O4 C5 C6 . . . . 162.65(18) ?
C7 O5 C6 C5 . . . . 31.7(7) ?
O4 C5 C6 O5 . . . . 65.4(3) ?
C8 C5 C6 O5 . . . . -55.5(3) ?
C8 O7 C7 O6 . . . . 176.2(6) ?
C8 O7 C7 O5 . . . . -0.2(11) ?
C6 O5 C7 O6 . . . . -178.7(6) ?
C6 O5 C7 O7 . . . . -2.2(11) ?
C7 O7 C8 C5 . . . . -27.2(7) ?
O4 C5 C8 O7 . . . . -65.0(2) ?
C6 C5 C8 O7 . . . . 52.6(3) ?
C3B O1B C1B O2B . . . . 172.(4) ?
C3B O1B C1B O3B . . . . 9.(5) ?
C2B O3B C1B O2B . . . . -174.(3) ?
C2B O3B C1B O1B . . . . -8.(4) ?
C1B O3B C2B C4B . . . . -111.(2) ?
C1B O3B C2B C3B . . . . 5.(3) ?
C1B O1B C3B C2B . . . . -5.(3) ?
C4B C2B C3B O1B . . . . 118.5(14) ?
O3B C2B C3B O1B . . . . -1.(2) ?
C5B O4B C4B C2B . . . . -171.1(9) ?
O3B C2B C4B O4B . . . . 59.7(14) ?
C3B C2B C4B O4B . . . . -60.9(13) ?
C4B O4B C5B C6B . . . . 159.7(13) ?
C4B O4B C5B C8B . . . . -79.8(11) ?
O4B C5B C6B O5B . . . . 66.(3) ?
C8B C5B C6B O5B . . . . -58.(3) ?
O4B C5B C8B O7B . . . . -65.8(12) ?
C6B C5B C8B O7B . . . . 59.6(15) ?

