# 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. 
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data_exp_8770
_database_code_depnum_ccdc_archive 'CCDC 1818895'
_audit_update_record             
;
2018-01-23 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 O5'
_chemical_formula_weight         276.28
_chemical_absolute_configuration rm
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.8641(4)
_cell_length_b                   9.4679(6)
_cell_length_c                   11.6419(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.465(6)
_cell_angle_gamma                90
_cell_volume                     644.39(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    868
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.1220
_cell_measurement_theta_min      3.7880
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.932
_exptl_absorpt_coefficient_mu    0.894
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.070
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2258
_diffrn_reflns_point_group_measured_fraction_full 0.681
_diffrn_reflns_point_group_measured_fraction_max 0.681
_diffrn_reflns_theta_full        67.247
_diffrn_reflns_theta_max         67.247
_diffrn_reflns_theta_min         3.808
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enhance (Cu) X-ray Source'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.280
_reflns_Friedel_fraction_full    0.319
_reflns_Friedel_fraction_max     0.319
_reflns_number_gt                1341
_reflns_number_total             1563
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    ?
_computing_publication_material  ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    ?
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 252 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         1563
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0506P)²+0.0929P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1107
_refine_special_details          ?
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.4439(6) 0.2921(4) -0.0410(2) 0.0604(9) Uani 1 1 d . . . . .
H1 H 0.3751 0.2716 0.0154 0.091 Uiso 1 1 calc R U . . .
O2 O 0.3519(5) 0.2956(4) 0.1702(2) 0.0590(9) Uani 1 1 d . . . . .
O3 O 0.7323(5) 0.6994(3) 0.2678(2) 0.0506(8) Uani 1 1 d . . . . .
H3 H 0.6946 0.7341 0.2046 0.076 Uiso 1 1 calc R U . . .
O4 O 0.7045(5) 0.1873(3) 0.3821(3) 0.0540(8) Uani 1 1 d . . . . .
H4 H 0.6545 0.1095 0.3984 0.081 Uiso 1 1 calc R U . . .
O5 O 0.3652(5) 0.4041(4) 0.5631(3) 0.0571(8) Uani 1 1 d . . . . .
H5 H 0.3076 0.3490 0.6068 0.086 Uiso 1 1 calc R U . . .
C1 C 1.0929(8) 0.5642(5) -0.1561(4) 0.0538(12) Uani 1 1 d . . . . .
H1A H 1.0954 0.4939 -0.2154 0.081 Uiso 1 1 calc R U . . .
H1B H 1.2451 0.5781 -0.1213 0.081 Uiso 1 1 calc R U . . .
H1C H 1.0360 0.6515 -0.1890 0.081 Uiso 1 1 calc R U . . .
C2 C 0.9394(7) 0.5156(4) -0.0657(3) 0.0410(9) Uani 1 1 d . . . . .
C3 C 0.7576(7) 0.4270(5) -0.0927(3) 0.0463(10) Uani 1 1 d . . . . .
H3A H 0.7281 0.3964 -0.1683 0.056 Uiso 1 1 calc R U . . .
C4 C 0.6170(6) 0.3822(5) -0.0090(3) 0.0416(9) Uani 1 1 d . . . . .
C5 C 0.6578(6) 0.4262(4) 0.1060(3) 0.0335(8) Uani 1 1 d . . . . .
C6 C 0.8409(6) 0.5208(4) 0.1320(3) 0.0336(8) Uani 1 1 d . . . . .
C7 C 0.9772(6) 0.5626(4) 0.0486(3) 0.0380(9) Uani 1 1 d . . . . .
H7 H 1.0983 0.6237 0.0679 0.046 Uiso 1 1 calc R U . . .
C8 C 0.5182(6) 0.3722(4) 0.1949(3) 0.0370(9) Uani 1 1 d . . . . .
C9 C 0.5789(6) 0.4131(4) 0.3192(3) 0.0339(8) Uani 1 1 d . . . . .
H9 H 0.4776 0.4909 0.3374 0.041 Uiso 1 1 calc R U . . .
C10 C 0.8257(6) 0.4666(4) 0.3399(3) 0.0357(8) Uani 1 1 d . . . . .
H10 H 0.9276 0.3865 0.3289 0.043 Uiso 1 1 calc R U . . .
C11 C 0.8784(7) 0.5796(4) 0.2534(3) 0.0386(9) Uani 1 1 d . . . . .
H11 H 1.0384 0.6089 0.2677 0.046 Uiso 1 1 calc R U . . .
C12 C 0.5403(7) 0.2929(4) 0.4031(3) 0.0399(9) Uani 1 1 d . . . . .
H12 H 0.3855 0.2548 0.3880 0.048 Uiso 1 1 calc R U . . .
C13 C 0.5747(7) 0.3449(5) 0.5273(3) 0.0453(10) Uani 1 1 d . . . . .
H13 H 0.6172 0.2641 0.5770 0.054 Uiso 1 1 calc R U . . .
C14 C 0.7543(7) 0.4556(5) 0.5465(3) 0.0505(11) Uani 1 1 d . . . . .
H14 H 0.7905 0.4864 0.6215 0.061 Uiso 1 1 calc R U . . .
C15 C 0.8651(7) 0.5127(5) 0.4638(3) 0.0473(10) Uani 1 1 d . . . . .
H15 H 0.9710 0.5837 0.4826 0.057 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 C4 1.356(5) . ?
O2 C8 1.231(5) . ?
O3 C11 1.439(5) . ?
O4 C12 1.422(5) . ?
O5 C13 1.441(4) . ?
C1 C2 1.509(6) . ?
C2 C3 1.373(6) . ?
C2 C7 1.404(5) . ?
C3 C4 1.391(5) . ?
C4 C5 1.404(5) . ?
C5 C6 1.413(5) . ?
C5 C8 1.461(5) . ?
C6 C7 1.363(5) . ?
C6 C11 1.520(5) . ?
C8 C9 1.514(5) . ?
C9 C10 1.535(5) . ?
C9 C12 1.528(5) . ?
C10 C11 1.518(5) . ?
C10 C15 1.507(5) . ?
C12 C13 1.526(6) . ?
C13 C14 1.490(6) . ?
C14 C15 1.318(6) . ?

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 C2 C1 121.4(4) . . ?
C3 C2 C7 118.2(3) . . ?
C7 C2 C1 120.4(4) . . ?
C2 C3 C4 121.2(4) . . ?
O1 C4 C3 118.1(4) . . ?
O1 C4 C5 121.2(3) . . ?
C3 C4 C5 120.7(4) . . ?
C4 C5 C6 117.5(3) . . ?
C4 C5 C8 120.5(3) . . ?
C6 C5 C8 121.9(3) . . ?
C5 C6 C11 118.9(3) . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 C11 120.4(3) . . ?
C6 C7 C2 121.6(4) . . ?
O2 C8 C5 121.3(3) . . ?
O2 C8 C9 119.8(3) . . ?
C5 C8 C9 119.0(3) . . ?
C8 C9 C10 112.6(3) . . ?
C8 C9 C12 112.7(3) . . ?
C12 C9 C10 109.3(3) . . ?
C11 C10 C9 111.5(3) . . ?
C15 C10 C9 108.6(3) . . ?
C15 C10 C11 114.0(3) . . ?
O3 C11 C6 110.6(3) . . ?
O3 C11 C10 108.9(3) . . ?
C10 C11 C6 109.7(3) . . ?
O4 C12 C9 106.1(3) . . ?
O4 C12 C13 110.4(3) . . ?
C13 C12 C9 110.5(3) . . ?
O5 C13 C12 110.3(3) . . ?
O5 C13 C14 106.9(4) . . ?
C14 C13 C12 114.1(3) . . ?
C15 C14 C13 124.2(4) . . ?
C14 C15 C10 122.2(4) . . ?

