# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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_ig266f2
_database_code_depnum_ccdc_archive 'CCDC 1559311'
_audit_update_record             
;
2017-06-29 deposited with the CCDC.
2017-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_structural     C11H14O6
_chemical_formula_sum            'C11 H14 O6'
_chemical_formula_weight         242.22

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7439(3)
_cell_length_b                   7.8264(3)
_cell_length_c                   9.1707(3)
_cell_angle_alpha                76.9720(13)
_cell_angle_beta                 81.6747(14)
_cell_angle_gamma                83.9592(14)
_cell_volume                     534.27(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9978
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      36.31

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9776
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27838
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.297
_diffrn_reflns_theta_max         36.317
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5181
_reflns_number_gt                4819
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT V8.34A'
_computing_data_reduction        'Bruker SAINT V8.34A'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5181
_refine_ls_number_parameters     161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0879
_refine_ls_wR_factor_gt          0.0863
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.42831(6) 0.25506(5) 0.38689(5) 0.01300(7) Uani 1 1 d . . . . .
O2 O 0.31311(5) 0.44357(5) 0.05665(4) 0.01066(7) Uani 1 1 d . . . . .
O3 O 0.31707(6) 0.79503(5) 0.05075(5) 0.01437(8) Uani 1 1 d . . . . .
O4 O 0.42529(5) 0.73062(5) 0.27390(5) 0.01193(7) Uani 1 1 d . . . . .
O5 O 0.06719(5) 0.58451(5) 0.33799(4) 0.01162(7) Uani 1 1 d . . . . .
H5 H 0.0895(17) 0.6227(17) 0.4132(15) 0.032(3) Uiso 1 1 d . . . . .
O6 O -0.10267(6) 0.23231(6) 0.44969(5) 0.01696(8) Uani 1 1 d . . . . .
C1 C 0.34785(6) 0.49333(6) 0.19108(5) 0.00874(8) Uani 1 1 d . . . . .
C2 C 0.50266(7) 0.37791(7) 0.25844(6) 0.01120(8) Uani 1 1 d . . . . .
H2A H 0.5701 0.3152 0.1835 0.013 Uiso 1 1 calc R U . . .
H2B H 0.5819 0.4510 0.2892 0.013 Uiso 1 1 calc R U . . .
C3 C 0.27703(7) 0.34520(7) 0.45020(6) 0.01182(8) Uani 1 1 d . . . . .
H3A H 0.3099 0.4293 0.5056 0.014 Uiso 1 1 calc R U . . .
H3B H 0.1999 0.2613 0.5201 0.014 Uiso 1 1 calc R U . . .
C4 C 0.18615(6) 0.44215(6) 0.31360(5) 0.00883(8) Uani 1 1 d . . . . .
C5 C 0.10203(6) 0.32335(6) 0.23944(5) 0.00957(8) Uani 1 1 d . . . . .
C6 C 0.17918(7) 0.33546(6) 0.09516(5) 0.00978(8) Uani 1 1 d . . . . .
C7 C 0.36292(6) 0.69010(6) 0.15913(5) 0.00945(8) Uani 1 1 d . . . . .
C8 C 0.42282(8) 0.91632(7) 0.27320(7) 0.01444(9) Uani 1 1 d . . . . .
H8A H 0.4945 0.9750 0.1823 0.022 Uiso 1 1 calc R U . . .
H8B H 0.4701 0.9307 0.3628 0.022 Uiso 1 1 calc R U . . .
H8C H 0.3022 0.9688 0.2740 0.022 Uiso 1 1 calc R U . . .
C9 C -0.03915(7) 0.21651(7) 0.32141(6) 0.01105(8) Uani 1 1 d . . . . .
C10 C -0.10577(8) 0.08125(7) 0.25456(6) 0.01455(9) Uani 1 1 d . . . . .
H10A H -0.0105 -0.0074 0.2367 0.022 Uiso 1 1 calc R U . . .
H10B H -0.1489 0.1386 0.1588 0.022 Uiso 1 1 calc R U . . .
H10C H -0.2013 0.0244 0.3246 0.022 Uiso 1 1 calc R U . . .
C11 C 0.14952(8) 0.25482(7) -0.03070(6) 0.01423(9) Uani 1 1 d . . . . .
H11A H 0.2034 0.3231 -0.1265 0.021 Uiso 1 1 calc R U . . .
H11B H 0.0235 0.2547 -0.0335 0.021 Uiso 1 1 calc R U . . .
H11C H 0.2022 0.1337 -0.0149 0.021 Uiso 1 1 calc R U . . .


_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 C3 1.4216(7) . ?
O1 C2 1.4328(7) . ?
O2 C6 1.3638(6) . ?
O2 C1 1.4416(6) . ?
O3 C7 1.2088(6) . ?
O4 C7 1.3310(6) . ?
O4 C8 1.4501(7) . ?
O5 C4 1.4060(6) . ?
O5 H5 0.856(13) . ?
O6 C9 1.2356(6) . ?
C1 C7 1.5151(7) . ?
C1 C2 1.5395(7) . ?
C1 C4 1.5767(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5345(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5140(7) . ?
C5 C6 1.3576(7) . ?
C5 C9 1.4596(7) . ?
C6 C11 1.4896(7) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.5039(7) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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
C3 O1 C2 106.23(4) . . ?
C6 O2 C1 108.23(4) . . ?
C7 O4 C8 116.43(4) . . ?
C4 O5 H5 110.5(9) . . ?
O2 C1 C7 109.53(4) . . ?
O2 C1 C2 111.05(4) . . ?
C7 C1 C2 115.80(4) . . ?
O2 C1 C4 106.28(4) . . ?
C7 C1 C4 109.86(4) . . ?
C2 C1 C4 103.78(4) . . ?
O1 C2 C1 106.29(4) . . ?
O1 C2 H2A 110.5 . . ?
C1 C2 H2A 110.5 . . ?
O1 C2 H2B 110.5 . . ?
C1 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
O1 C3 C4 104.33(4) . . ?
O1 C3 H3A 110.9 . . ?
C4 C3 H3A 110.9 . . ?
O1 C3 H3B 110.9 . . ?
C4 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
O5 C4 C5 109.84(4) . . ?
O5 C4 C3 115.40(4) . . ?
C5 C4 C3 114.28(4) . . ?
O5 C4 C1 114.58(4) . . ?
C5 C4 C1 100.07(4) . . ?
C3 C4 C1 101.51(4) . . ?
C6 C5 C9 129.13(5) . . ?
C6 C5 C4 109.51(4) . . ?
C9 C5 C4 121.36(4) . . ?
C5 C6 O2 113.61(4) . . ?
C5 C6 C11 133.65(5) . . ?
O2 C6 C11 112.74(4) . . ?
O3 C7 O4 125.18(5) . . ?
O3 C7 C1 125.59(5) . . ?
O4 C7 C1 109.11(4) . . ?
O4 C8 H8A 109.5 . . ?
O4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O6 C9 C5 120.20(5) . . ?
O6 C9 C10 118.70(5) . . ?
C5 C9 C10 121.06(4) . . ?
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 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
C6 O2 C1 C7 -133.00(4) . . . . ?
C6 O2 C1 C2 97.86(5) . . . . ?
C6 O2 C1 C4 -14.37(5) . . . . ?
C3 O1 C2 C1 -33.69(5) . . . . ?
O2 C1 C2 O1 -103.86(4) . . . . ?
C7 C1 C2 O1 130.42(4) . . . . ?
C4 C1 C2 O1 9.95(5) . . . . ?
C2 O1 C3 C4 44.08(5) . . . . ?
O1 C3 C4 O5 -159.93(4) . . . . ?
O1 C3 C4 C5 71.29(5) . . . . ?
O1 C3 C4 C1 -35.42(5) . . . . ?
O2 C1 C4 O5 -102.83(4) . . . . ?
C7 C1 C4 O5 15.57(5) . . . . ?
C2 C1 C4 O5 139.98(4) . . . . ?
O2 C1 C4 C5 14.57(5) . . . . ?
C7 C1 C4 C5 132.97(4) . . . . ?
C2 C1 C4 C5 -102.62(4) . . . . ?
O2 C1 C4 C3 132.11(4) . . . . ?
C7 C1 C4 C3 -109.49(4) . . . . ?
C2 C1 C4 C3 14.93(5) . . . . ?
O5 C4 C5 C6 110.60(5) . . . . ?
C3 C4 C5 C6 -117.88(5) . . . . ?
C1 C4 C5 C6 -10.28(5) . . . . ?
O5 C4 C5 C9 -69.77(6) . . . . ?
C3 C4 C5 C9 61.75(6) . . . . ?
C1 C4 C5 C9 169.35(4) . . . . ?
C9 C5 C6 O2 -177.43(5) . . . . ?
C4 C5 C6 O2 2.17(6) . . . . ?
C9 C5 C6 C11 2.17(10) . . . . ?
C4 C5 C6 C11 -178.23(5) . . . . ?
C1 O2 C6 C5 8.13(6) . . . . ?
C1 O2 C6 C11 -171.55(4) . . . . ?
C8 O4 C7 O3 5.63(8) . . . . ?
C8 O4 C7 C1 -170.78(4) . . . . ?
O2 C1 C7 O3 14.60(7) . . . . ?
C2 C1 C7 O3 141.10(5) . . . . ?
C4 C1 C7 O3 -101.78(6) . . . . ?
O2 C1 C7 O4 -169.01(4) . . . . ?
C2 C1 C7 O4 -42.52(6) . . . . ?
C4 C1 C7 O4 74.61(5) . . . . ?
C6 C5 C9 O6 -174.40(5) . . . . ?
C4 C5 C9 O6 6.05(8) . . . . ?
C6 C5 C9 C10 7.79(8) . . . . ?
C4 C5 C9 C10 -171.77(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5 O6 0.856(13) 1.893(13) 2.7236(6) 163.1(13) 2_566
C10 H10B O3 0.98 2.41 3.3504(7) 161.6 2_565
C2 H2A O3 0.99 2.50 3.4651(7) 164.4 2_665
C8 H8B O1 0.98 2.60 3.4169(7) 140.5 2_666

_refine_diff_density_max         0.581
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.054

