# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2046641'
loop_
_audit_author_name
_audit_author_address
'Kana Sureshan'
;IISER Thiruvananthapuram
India
;
_audit_update_record             
;
2020-11-26 deposited with the CCDC.	2021-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H34 O9'
_chemical_formula_sum            'C16 H34 O9'
_chemical_formula_weight         370.43

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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   14.4368(11)
_cell_length_b                   4.9452(4)
_cell_length_c                   12.9747(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.740(4)
_cell_angle_gamma                90
_cell_volume                     923.13(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2442
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      28.34

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.332
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9719
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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 0
_diffrn_reflns_number            3993
_diffrn_reflns_av_unetI/netI     0.0826
_diffrn_reflns_av_R_equivalents  0.1379
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.832
_diffrn_reflns_theta_max         25.980
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1748
_reflns_number_gt                1571
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1038P)²] 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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -2(2)
_chemical_absolute_configuration RM
_refine_ls_number_reflns         1748
_refine_ls_number_parameters     124
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1570
_refine_ls_wR_factor_gt          0.1522
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.061
_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
C1 C 0.3355(2) 0.9048(7) 0.6623(2) 0.0376(8) Uani 1 1 d . . . . .
H1 H 0.3181 1.0951 0.6523 0.045 Uiso 1 1 calc R U . . .
C2 C 0.2498(3) 0.7292(9) 0.6369(3) 0.0439(8) Uani 1 1 d . . . . .
H2A H 0.2445 0.6981 0.5628 0.053 Uiso 1 1 calc R U . . .
H2B H 0.2615 0.5551 0.6698 0.053 Uiso 1 1 calc R U . . .
C3 C 0.1559(2) 0.8282(9) 0.6663(3) 0.0462(10) Uani 1 1 d . . . . .
H3A H 0.1160 0.6716 0.6707 0.055 Uiso 1 1 calc R U . . .
H3B H 0.1290 0.9396 0.6101 0.055 Uiso 1 1 calc R U . . .
C4 C 0.1525(2) 0.9890(8) 0.7664(3) 0.0361(7) Uani 1 1 d . . . . .
H4 H 0.1704 1.1756 0.7522 0.043 Uiso 1 1 calc R U . . .
C5 C 0.2170(2) 0.8875(6) 0.8573(2) 0.0307(7) Uani 1 1 d . . . . .
H5 H 0.1931 0.9591 0.9203 0.037 Uiso 1 1 calc R U . . .
C6 C 0.3165(2) 0.9916(7) 0.8548(2) 0.0304(7) Uani 1 1 d . . . . .
H6 H 0.3140 1.1872 0.8426 0.037 Uiso 1 1 calc R U . . .
C7 C 0.3745(2) 0.8639(7) 0.7748(2) 0.0299(7) Uani 1 1 d . . . . .
H7 H 0.3796 0.6695 0.7887 0.036 Uiso 1 1 calc R U . . .
C8 C 0.4099(3) 0.8329(12) 0.5883(3) 0.0605(13) Uani 1 1 d . . . . .
H8A H 0.3860 0.8681 0.5183 0.091 Uiso 1 1 calc R U . . .
H8B H 0.4257 0.6450 0.5957 0.091 Uiso 1 1 calc R U . . .
H8C H 0.4644 0.9410 0.6048 0.091 Uiso 1 1 calc R U . . .
O1 O 0.05873(16) 0.9940(6) 0.7958(2) 0.0472(7) Uani 1 1 d . . . . .
H1A H 0.0362 0.8420 0.7898 0.071 Uiso 1 1 calc R U . . .
O1' O 0.5000 1.3502(12) 1.0000 0.0616(12) Uani 1 2 d DS T P . .
O2 O 0.21239(19) 0.6026(5) 0.86343(18) 0.0383(6) Uani 1 1 d . . . . .
H2 H 0.1924 0.5589 0.9184 0.057 Uiso 1 1 calc R U . . .
O3 O 0.36125(17) 0.9452(6) 0.95596(17) 0.0427(7) Uani 1 1 d . . . . .
H3 H 0.4100 1.0307 0.9627 0.064 Uiso 1 1 calc R U . . .
O4 O 0.46546(15) 0.9834(6) 0.79180(19) 0.0393(6) Uani 1 1 d . . . . .
H4A H 0.5050 0.8640 0.7940 0.059 Uiso 1 1 calc R U . . .
H1' H 0.488(4) 1.459(13) 1.057(4) 0.10(2) Uiso 1 1 d D . . . .


_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
C1 C2 1.525(5) . ?
C1 C7 1.534(4) . ?
C1 C8 1.540(5) . ?
C1 H1 0.9800 . ?
C2 C3 1.519(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.528(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O1 1.437(4) . ?
C4 C5 1.525(4) . ?
C4 H4 0.9800 . ?
C5 O2 1.413(4) . ?
C5 C6 1.528(4) . ?
C5 H5 0.9800 . ?
C6 O3 1.432(4) . ?
C6 C7 1.524(4) . ?
C6 H6 0.9800 . ?
C7 O4 1.441(4) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
O1 H1A 0.8200 . ?
O1' H1' 0.94(2) . ?
O2 H2 0.8200 . ?
O3 H3 0.8200 . ?
O4 H4A 0.8200 . ?

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
C2 C1 C7 111.0(3) . . ?
C2 C1 C8 109.2(3) . . ?
C7 C1 C8 110.1(3) . . ?
C2 C1 H1 108.8 . . ?
C7 C1 H1 108.8 . . ?
C8 C1 H1 108.8 . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2A 107.5 . . ?
C1 C2 H2A 107.5 . . ?
C3 C2 H2B 107.5 . . ?
C1 C2 H2B 107.5 . . ?
H2A C2 H2B 107.0 . . ?
C2 C3 C4 118.3(3) . . ?
C2 C3 H3A 107.7 . . ?
C4 C3 H3A 107.7 . . ?
C2 C3 H3B 107.7 . . ?
C4 C3 H3B 107.7 . . ?
H3A C3 H3B 107.1 . . ?
O1 C4 C5 109.2(3) . . ?
O1 C4 C3 109.4(3) . . ?
C5 C4 C3 115.2(3) . . ?
O1 C4 H4 107.6 . . ?
C5 C4 H4 107.6 . . ?
C3 C4 H4 107.6 . . ?
O2 C5 C4 110.1(3) . . ?
O2 C5 C6 112.7(3) . . ?
C4 C5 C6 112.8(3) . . ?
O2 C5 H5 107.0 . . ?
C4 C5 H5 107.0 . . ?
C6 C5 H5 107.0 . . ?
O3 C6 C7 109.0(3) . . ?
O3 C6 C5 106.3(2) . . ?
C7 C6 C5 116.4(3) . . ?
O3 C6 H6 108.3 . . ?
C7 C6 H6 108.3 . . ?
C5 C6 H6 108.3 . . ?
O4 C7 C6 105.8(2) . . ?
O4 C7 C1 110.4(3) . . ?
C6 C7 C1 114.5(3) . . ?
O4 C7 H7 108.7 . . ?
C6 C7 H7 108.7 . . ?
C1 C7 H7 108.7 . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 O1 H1A 109.5 . . ?
C5 O2 H2 109.5 . . ?
C6 O3 H3 109.5 . . ?
C7 O4 H4A 109.5 . . ?

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
C4 H4 O2 0.98 2.60 3.370(5) 135.4 1_565
C6 H6 O2 0.98 2.55 3.380(4) 142.3 1_565
O1 H1A O4 0.82 2.05 2.860(4) 170.6 3_445
O2 H2 O3 0.82 1.94 2.764(3) 176.6 4_547
O3 H3 O1' 0.82 2.08 2.857(5) 158.7 .
O4 H4A O1 0.82 1.99 2.768(4) 159.0 3_545
O1' H1' O1 0.94(2) 2.09(4) 2.935(3) 149(7) 4_557
C4 H4 O2 0.98 2.60 3.370(5) 135.4 1_565
C6 H6 O2 0.98 2.55 3.380(4) 142.3 1_565
O1 H1A O4 0.82 2.05 2.860(4) 170.6 3_445
O2 H2 O3 0.82 1.94 2.764(3) 176.6 4_547
O3 H3 O1' 0.82 2.08 2.857(5) 158.7 .
O4 H4A O1 0.82 1.99 2.768(4) 159.0 3_545
O1' H1' O1 0.94(2) 2.09(4) 2.935(3) 149(7) 4_557

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.060

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2046642'
loop_
_audit_author_name
_audit_author_address
'Kana Sureshan'
;IISER Thiruvananthapuram
India
;
_audit_update_record             
;
2020-11-26 deposited with the CCDC.	2021-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H22 O6'
_chemical_formula_sum            'C15 H22 O6'
_chemical_formula_weight         298.32
_chemical_absolute_configuration rm

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      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                   4.7565(2)
_cell_length_b                   25.9753(13)
_cell_length_c                   6.1401(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.072(3)
_cell_angle_gamma                90
_cell_volume                     756.70(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3238
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      27.81

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.308
_exptl_crystal_density_method    NONE
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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 0
_diffrn_reflns_number            6338
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.137
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_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 0.906
_diffrn_reflns_point_group_measured_fraction_full 0.911
_reflns_number_total             2695
_reflns_number_gt                2418
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_max     0.808
_reflns_Friedel_fraction_full    0.819

_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'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0730P)²+0.2333P] 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 987 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(4)
_refine_ls_number_reflns         2695
_refine_ls_number_parameters     203
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1240
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
C1 C 0.6148(9) -0.08267(15) 0.4271(6) 0.0409(9) Uani 1 1 d . . . . .
H1A H 0.7456 -0.0996 0.5324 0.049 Uiso 1 1 calc R U . . .
H1B H 0.4826 -0.1084 0.3679 0.049 Uiso 1 1 calc R U . . .
C2 C 0.4557(7) -0.04174(14) 0.5420(5) 0.0330(7) Uani 1 1 d . . . . .
H2 H 0.3424 -0.0591 0.6471 0.040 Uiso 1 1 calc R U . . .
C3 C 0.6492(7) -0.00354(12) 0.6693(5) 0.0281(7) Uani 1 1 d . . . . .
H3 H 0.7611 0.0145 0.5652 0.034 Uiso 1 1 calc R U . . .
C4 C 0.4851(7) 0.03686(13) 0.7926(5) 0.0306(7) Uani 1 1 d . . . . .
H4 H 0.3398 0.0523 0.6919 0.037 Uiso 1 1 calc R U . . .
C5 C 0.6789(8) 0.07843(14) 0.8838(6) 0.0371(8) Uani 1 1 d . . . . .
C6 C 0.7896(11) 0.07879(18) 1.0872(7) 0.0557(11) Uani 1 1 d D . . . .
C7 C 0.7609(9) 0.11820(16) 0.7236(7) 0.0466(9) Uani 1 1 d . . . . .
H7A H 0.9052 0.1405 0.7918 0.056 Uiso 1 1 calc R U . . .
H7B H 0.8373 0.1015 0.5994 0.056 Uiso 1 1 calc R U . . .
C8 C 0.5734(13) 0.1783(2) 0.4709(10) 0.0758(17) Uani 1 1 d . . . . .
H8A H 0.5890 0.1562 0.3449 0.091 Uiso 1 1 calc R U . . .
H8B H 0.7522 0.1959 0.4993 0.091 Uiso 1 1 calc R U . . .
C9 C 0.3481(9) 0.21712(15) 0.4200(7) 0.0465(10) Uani 1 1 d . . . . .
C10 C 0.2714(11) 0.25306(19) 0.5703(8) 0.0588(12) Uani 1 1 d . . . . .
H10 H 0.3553 0.2512 0.7116 0.071 Uiso 1 1 calc R U . . .
C11 C 0.0847(13) 0.29024(19) 0.5248(8) 0.0608(13) Uani 1 1 d . . . . .
H11 H 0.0376 0.3130 0.6333 0.073 Uiso 1 1 calc R U . . .
C12 C -0.0350(11) 0.29473(16) 0.3225(7) 0.0529(11) Uani 1 1 d . . . . .
C13 C 0.0190(11) 0.26183(18) 0.1591(7) 0.0586(12) Uani 1 1 d . . . . .
H13 H -0.0679 0.2658 0.0197 0.070 Uiso 1 1 calc R U . . .
C14 C 0.2164(12) 0.2203(2) 0.2086(8) 0.0640(13) Uani 1 1 d . . . . .
H14 H 0.2551 0.1962 0.1025 0.077 Uiso 1 1 calc R U . . .
C15 C -0.3403(16) 0.3450(2) 0.0735(9) 0.0802(17) Uani 1 1 d . . . . .
H15A H -0.3830 0.3128 0.0018 0.120 Uiso 1 1 calc R U . . .
H15B H -0.2067 0.3637 -0.0059 0.120 Uiso 1 1 calc R U . . .
H15C H -0.5099 0.3648 0.0789 0.120 Uiso 1 1 calc R U . . .
O1 O 0.7667(5) -0.06234(11) 0.2554(4) 0.0414(6) Uani 1 1 d . . . . .
H1 H 0.9115 -0.0485 0.3069 0.062 Uiso 1 1 calc R U . . .
O2 O 0.2659(5) -0.01436(11) 0.3922(3) 0.0400(6) Uani 1 1 d . . . . .
H2A H 0.3519 -0.0036 0.2905 0.060 Uiso 1 1 calc R U . . .
O3 O 0.8384(5) -0.03086(9) 0.8197(3) 0.0323(5) Uani 1 1 d . . . . .
H3A H 0.7574 -0.0382 0.9290 0.049 Uiso 1 1 calc R U . . .
O4 O 0.3532(5) 0.01129(10) 0.9635(3) 0.0356(6) Uani 1 1 d . . . . .
H4A H 0.2039 -0.0014 0.9147 0.053 Uiso 1 1 calc R U . . .
O5 O 0.5199(6) 0.14790(11) 0.6523(5) 0.0512(7) Uani 1 1 d . . . . .
O6 O -0.2270(9) 0.33575(14) 0.2840(6) 0.0756(11) Uani 1 1 d . . . . .
H6A H 0.749(14) 0.053(2) 1.195(9) 0.10(2) Uiso 1 1 d D . . . .
H6B H 0.930(8) 0.1043(15) 1.138(7) 0.053(13) Uiso 1 1 d D . . . .


_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
C1 O1 1.422(4) . ?
C1 C2 1.508(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 O2 1.432(4) . ?
C2 C3 1.530(4) . ?
C2 H2 0.9800 . ?
C3 O3 1.431(4) . ?
C3 C4 1.539(4) . ?
C3 H3 0.9800 . ?
C4 O4 1.424(4) . ?
C4 C5 1.502(5) . ?
C4 H4 0.9800 . ?
C5 C6 1.321(6) . ?
C5 C7 1.497(5) . ?
C6 H6A 0.97(2) . ?
C6 H6B 0.97(2) . ?
C7 O5 1.425(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O5 1.404(5) . ?
C8 C9 1.488(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.380(6) . ?
C9 C14 1.403(7) . ?
C10 C11 1.328(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.334(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.356(6) . ?
C12 O6 1.412(6) . ?
C13 C14 1.449(7) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 O6 1.385(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O1 H1 0.8200 . ?
O2 H2A 0.8200 . ?
O3 H3A 0.8200 . ?
O4 H4A 0.8200 . ?

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
O1 C1 C2 112.5(3) . . ?
O1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
O1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
O2 C2 C1 111.4(3) . . ?
O2 C2 C3 109.6(3) . . ?
C1 C2 C3 113.1(3) . . ?
O2 C2 H2 107.5 . . ?
C1 C2 H2 107.5 . . ?
C3 C2 H2 107.5 . . ?
O3 C3 C2 109.6(3) . . ?
O3 C3 C4 109.8(2) . . ?
C2 C3 C4 112.7(3) . . ?
O3 C3 H3 108.2 . . ?
C2 C3 H3 108.2 . . ?
C4 C3 H3 108.2 . . ?
O4 C4 C5 110.6(2) . . ?
O4 C4 C3 108.1(3) . . ?
C5 C4 C3 110.8(3) . . ?
O4 C4 H4 109.1 . . ?
C5 C4 H4 109.1 . . ?
C3 C4 H4 109.1 . . ?
C6 C5 C7 120.8(4) . . ?
C6 C5 C4 123.4(4) . . ?
C7 C5 C4 115.7(3) . . ?
C5 C6 H6A 124(4) . . ?
C5 C6 H6B 122(3) . . ?
H6A C6 H6B 115(5) . . ?
O5 C7 C5 109.5(3) . . ?
O5 C7 H7A 109.8 . . ?
C5 C7 H7A 109.8 . . ?
O5 C7 H7B 109.8 . . ?
C5 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
O5 C8 C9 112.3(4) . . ?
O5 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
O5 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C14 117.2(4) . . ?
C10 C9 C8 122.6(5) . . ?
C14 C9 C8 120.1(5) . . ?
C11 C10 C9 123.8(5) . . ?
C11 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
C10 C11 C12 119.6(5) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 122.9(4) . . ?
C11 C12 O6 116.7(4) . . ?
C13 C12 O6 120.4(4) . . ?
C12 C13 C14 117.9(4) . . ?
C12 C13 H13 121.0 . . ?
C14 C13 H13 121.0 . . ?
C9 C14 C13 118.5(4) . . ?
C9 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
O6 C15 H15A 109.5 . . ?
O6 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O6 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 O1 H1 109.5 . . ?
C2 O2 H2A 109.5 . . ?
C3 O3 H3A 109.5 . . ?
C4 O4 H4A 109.5 . . ?
C8 O5 C7 111.2(3) . . ?
C15 O6 C12 119.4(4) . . ?

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
O1 H1 O2 0.82 1.94 2.759(3) 172.9 1_655
O2 H2A O4 0.82 2.04 2.775(3) 148.1 1_554
O3 H3A O1 0.82 2.10 2.841(3) 150.8 1_556
O3 H3A O4 0.82 2.33 2.756(3) 112.6 .
O4 H4A O3 0.82 1.95 2.769(3) 175.8 1_455

_refine_diff_density_max         0.581
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.043

_shelxl_version_number           2014-3

