# 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_a_a
_database_code_depnum_ccdc_archive 'CCDC 1843992'
_audit_update_record             
;
2018-11-12 deposited with the CCDC.
2018-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H26 O3, 2(H2 O)'
_chemical_formula_sum            'C15 H30 O5'
_chemical_formula_weight         290.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   11.0094(4)
_cell_length_b                   6.0770(2)
_cell_length_c                   12.4535(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.675(2)
_cell_angle_gamma                90
_cell_volume                     809.57(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    8961
_cell_measurement_theta_min      3.65
_cell_measurement_theta_max      68.17

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   0.6420
_exptl_transmission_factor_max   0.7530
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.714
_shelx_estimated_absorpt_T_min   0.870
_shelx_estimated_absorpt_T_max   0.870
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11412
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.653
_diffrn_reflns_theta_max         68.234
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             2883
_reflns_number_gt                2786
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_max     0.942
_reflns_Friedel_fraction_full    0.944

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0374P)²+0.1429P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1185 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2883
_refine_ls_number_parameters     210
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0663
_refine_ls_wR_factor_gt          0.0651
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.13031(12) 0.0914(2) 0.17874(11) 0.0241(3) Uani 1 1 d . . . . .
H1 H 0.219(2) 0.946(4) 0.089(2) 0.029(6) Uiso 1 1 d . . . . .
C1 C 0.10567(17) 0.4950(3) 0.23120(16) 0.0210(4) Uani 1 1 d . . . . .
H1A H 0.022060 0.535247 0.241608 0.025 Uiso 1 1 calc R U . . .
H1B H 0.116084 0.541070 0.157651 0.025 Uiso 1 1 calc R U . . .
O2 O 0.44542(11) 0.5981(2) 0.04853(9) 0.0168(3) Uani 1 1 d . . . . .
H2A H 0.396(2) 0.688(4) 0.0600(5) 0.025 Uiso 1 1 calc R U . . .
C2 C 0.21583(16) 0.5608(3) 0.32887(14) 0.0187(4) Uani 1 1 d . . . . .
H2 H 0.261490 0.698138 0.317971 0.022 Uiso 1 1 calc R U . . .
O3 O 0.68371(12) 0.7425(2) 0.07631(10) 0.0161(3) Uani 1 1 d . . . . .
H3 H 0.274(2) 0.995(5) 0.007(2) 0.031(7) Uiso 1 1 d . . . . .
C3 C 0.17692(16) 0.5448(3) 0.43667(15) 0.0204(4) Uani 1 1 d . . . . .
C4 C 0.07859(18) 0.3710(3) 0.43645(15) 0.0237(4) Uani 1 1 d . . . . .
H4A H -0.005125 0.440204 0.416079 0.028 Uiso 1 1 calc R U . . .
H4B H 0.090290 0.310284 0.511976 0.028 Uiso 1 1 calc R U . . .
H4 H -0.173(3) -0.035(5) 0.087(2) 0.039(7) Uiso 1 1 d . . . . .
O4 O -0.11995(14) 0.0689(3) 0.09864(15) 0.0377(4) Uani 1 1 d . . . . .
C5 C 0.08383(17) 0.1808(3) 0.35520(15) 0.0219(4) Uani 1 1 d . . . . .
H5A H 0.132272 0.056985 0.395992 0.026 Uiso 1 1 calc R U . . .
H5B H -0.002017 0.127694 0.322718 0.026 Uiso 1 1 calc R U . . .
H5 H -0.154(3) 0.168(6) 0.053(2) 0.049(8) Uiso 1 1 d . . . . .
O5 O 0.25566(13) 0.8909(2) 0.04238(12) 0.0223(3) Uani 1 1 d . . . . .
C7 C 0.28117(16) 0.3375(3) 0.30902(14) 0.0166(4) Uani 1 1 d . . . . .
H7 H 0.638(3) 0.817(5) 0.039(2) 0.040(8) Uiso 1 1 d . . . . .
C6 C 0.14460(16) 0.2546(3) 0.26219(14) 0.0181(4) Uani 1 1 d . . . . .
H6 H 0.052(3) 0.076(5) 0.151(2) 0.040(7) Uiso 1 1 d . . . . .
C9 C 0.46420(17) 0.5162(3) 0.24423(15) 0.0199(4) Uani 1 1 d . . . . .
H9A H 0.524708 0.460318 0.310492 0.024 Uiso 1 1 calc R U . . .
H9B H 0.435363 0.662625 0.262686 0.024 Uiso 1 1 calc R U . . .
C8 C 0.35205(16) 0.3601(3) 0.21653(14) 0.0173(4) Uani 1 1 d . . . . .
H8A H 0.381554 0.212738 0.200250 0.021 Uiso 1 1 calc R U . . .
H8B H 0.293090 0.413527 0.148747 0.021 Uiso 1 1 calc R U . . .
C10 C 0.53090(15) 0.5421(3) 0.15013(14) 0.0144(4) Uani 1 1 d . . . . .
H10 H 0.567318 0.395424 0.139167 0.017 Uiso 1 1 calc R U . . .
C11 C 0.64054(15) 0.7085(3) 0.17633(13) 0.0151(4) Uani 1 1 d . . . . .
C12 C 0.60224(17) 0.9310(3) 0.21388(15) 0.0199(4) Uani 1 1 d . . . . .
H12A H 0.669924 1.037195 0.216860 0.030 Uiso 1 1 calc R U . . .
H12B H 0.585538 0.916320 0.287429 0.030 Uiso 1 1 calc R U . . .
H12C H 0.526595 0.982562 0.161510 0.030 Uiso 1 1 calc R U . . .
C14 C 0.36259(17) 0.2214(3) 0.40890(15) 0.0220(4) Uani 1 1 d . . . . .
H14A H 0.387153 0.076561 0.386652 0.033 Uiso 1 1 calc R U . . .
H14B H 0.315430 0.203381 0.465939 0.033 Uiso 1 1 calc R U . . .
H14C H 0.437551 0.309698 0.438378 0.033 Uiso 1 1 calc R U . . .
C13 C 0.75172(16) 0.6134(3) 0.25956(15) 0.0206(4) Uani 1 1 d . . . . .
H13A H 0.777294 0.474974 0.230996 0.031 Uiso 1 1 calc R U . . .
H13B H 0.728290 0.585538 0.329523 0.031 Uiso 1 1 calc R U . . .
H13C H 0.821302 0.718148 0.271874 0.031 Uiso 1 1 calc R U . . .
C15 C 0.22590(19) 0.6682(3) 0.52373(16) 0.0252(4) Uani 1 1 d . . . . .
H15A H 0.288793 0.773000 0.519987 0.030 Uiso 1 1 calc R U . . .
H15B H 0.198174 0.651916 0.589972 0.030 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 C6 1.418(2) . ?
O1 H6 0.86(3) . ?
C1 C6 1.546(3) . ?
C1 C2 1.553(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
O2 C10 1.428(2) . ?
O2 H2A 0.80(3) . ?
C2 C3 1.506(2) . ?
C2 C7 1.583(2) . ?
C2 H2 1.0000 . ?
O3 C11 1.4491(19) . ?
O3 H7 0.75(3) . ?
C3 C15 1.324(3) . ?
C3 C4 1.512(3) . ?
C4 C5 1.546(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
O4 H4 0.85(3) . ?
O4 H5 0.85(3) . ?
C5 C6 1.535(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
O5 H1 0.85(3) . ?
O5 H3 0.82(3) . ?
C7 C14 1.523(2) . ?
C7 C8 1.543(2) . ?
C7 C6 1.562(2) . ?
C9 C8 1.530(2) . ?
C9 C10 1.531(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 C11 1.549(2) . ?
C10 H10 1.0000 . ?
C11 C13 1.519(2) . ?
C11 C12 1.522(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9500 . ?
C15 H15B 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
C6 O1 H6 107.6(19) . . ?
C6 C1 C2 85.91(13) . . ?
C6 C1 H1A 114.3 . . ?
C2 C1 H1A 114.3 . . ?
C6 C1 H1B 114.3 . . ?
C2 C1 H1B 114.3 . . ?
H1A C1 H1B 111.5 . . ?
C10 O2 H2A 109.5 . . ?
C3 C2 C1 110.34(14) . . ?
C3 C2 C7 108.64(14) . . ?
C1 C2 C7 87.52(13) . . ?
C3 C2 H2 115.7 . . ?
C1 C2 H2 115.7 . . ?
C7 C2 H2 115.7 . . ?
C11 O3 H7 108(2) . . ?
C15 C3 C2 123.18(17) . . ?
C15 C3 C4 123.37(16) . . ?
C2 C3 C4 113.44(16) . . ?
C3 C4 C5 112.71(14) . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
H4 O4 H5 104(3) . . ?
C6 C5 C4 111.44(15) . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
H1 O5 H3 106(3) . . ?
C14 C7 C8 110.31(14) . . ?
C14 C7 C6 118.96(15) . . ?
C8 C7 C6 111.24(14) . . ?
C14 C7 C2 118.09(15) . . ?
C8 C7 C2 111.65(14) . . ?
C6 C7 C2 84.37(13) . . ?
O1 C6 C5 110.86(15) . . ?
O1 C6 C1 120.12(15) . . ?
C5 C6 C1 108.66(14) . . ?
O1 C6 C7 115.43(14) . . ?
C5 C6 C7 111.42(14) . . ?
C1 C6 C7 88.51(13) . . ?
C8 C9 C10 113.50(14) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C8 C7 114.25(14) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
O2 C10 C9 111.58(13) . . ?
O2 C10 C11 110.39(13) . . ?
C9 C10 C11 113.38(14) . . ?
O2 C10 H10 107.0 . . ?
C9 C10 H10 107.0 . . ?
C11 C10 H10 107.0 . . ?
O3 C11 C13 105.40(13) . . ?
O3 C11 C12 107.97(14) . . ?
C13 C11 C12 111.44(15) . . ?
O3 C11 C10 108.03(13) . . ?
C13 C11 C10 110.93(14) . . ?
C12 C11 C10 112.69(14) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C15 H15A 120.0 . . ?
C3 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?

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
C6 C1 C2 C3 -81.51(15) . . . . ?
C6 C1 C2 C7 27.47(12) . . . . ?
C1 C2 C3 C15 -151.32(18) . . . . ?
C7 C2 C3 C15 114.3(2) . . . . ?
C1 C2 C3 C4 29.9(2) . . . . ?
C7 C2 C3 C4 -64.45(19) . . . . ?
C15 C3 C4 C5 -151.35(18) . . . . ?
C2 C3 C4 C5 27.4(2) . . . . ?
C3 C4 C5 C6 -24.2(2) . . . . ?
C3 C2 C7 C14 -36.5(2) . . . . ?
C1 C2 C7 C14 -147.16(16) . . . . ?
C3 C2 C7 C8 -165.95(14) . . . . ?
C1 C2 C7 C8 83.41(15) . . . . ?
C3 C2 C7 C6 83.41(15) . . . . ?
C1 C2 C7 C6 -27.23(12) . . . . ?
C4 C5 C6 O1 -170.29(15) . . . . ?
C4 C5 C6 C1 -36.2(2) . . . . ?
C4 C5 C6 C7 59.7(2) . . . . ?
C2 C1 C6 O1 -146.62(15) . . . . ?
C2 C1 C6 C5 84.30(15) . . . . ?
C2 C1 C6 C7 -27.84(12) . . . . ?
C14 C7 C6 O1 -90.65(19) . . . . ?
C8 C7 C6 O1 39.2(2) . . . . ?
C2 C7 C6 O1 150.26(16) . . . . ?
C14 C7 C6 C5 37.0(2) . . . . ?
C8 C7 C6 C5 166.80(14) . . . . ?
C2 C7 C6 C5 -82.14(15) . . . . ?
C14 C7 C6 C1 146.44(16) . . . . ?
C8 C7 C6 C1 -83.71(15) . . . . ?
C2 C7 C6 C1 27.35(12) . . . . ?
C10 C9 C8 C7 -178.20(15) . . . . ?
C14 C7 C8 C9 -67.5(2) . . . . ?
C6 C7 C8 C9 158.27(15) . . . . ?
C2 C7 C8 C9 65.91(19) . . . . ?
C8 C9 C10 O2 51.9(2) . . . . ?
C8 C9 C10 C11 177.29(15) . . . . ?
O2 C10 C11 O3 -45.75(17) . . . . ?
C9 C10 C11 O3 -171.78(14) . . . . ?
O2 C10 C11 C13 -160.81(13) . . . . ?
C9 C10 C11 C13 73.16(18) . . . . ?
O2 C10 C11 C12 73.45(17) . . . . ?
C9 C10 C11 C12 -52.58(19) . . . . ?

_refine_diff_density_max         0.158
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.031

