# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_mx382
_database_code_depnum_ccdc_archive 'CCDC 861573'
_audit_update_record             
;
2012-01-09 deposited with the CCDC.
2016-11-09 downloaded from the CCDC.
;
#TrackingRef 'mx382.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H24 O5'
_chemical_formula_weight         284.34
_chemical_absolute_configuration unk

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.5709(11)
_cell_length_b                   15.994(3)
_cell_length_c                   16.547(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1474.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4972
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9785
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'MM007HF + CCD (Saturn724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13237
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1947
_reflns_number_gt                1885
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Mercury: visualization and analysis of crystal structures, C. F. Macrae,
P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0499P)²+0.3929P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack parameter cannot be determined correctly because the crystal consists of
light atoms only, and because the radiation is MoKα. In the final stage of
structure refinement with SHELXL, MERG 3 card was used, i.e. Friedel pairs
were merged.

Flack H D (1983), Acta Cryst. A39, 876-881
;
_refine_ls_abs_structure_Flack   -0.6(15)
_refine_ls_number_reflns         1947
_refine_ls_number_parameters     204
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.106
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O -0.3623(4) 0.48586(11) 0.42003(11) 0.0374(5) Uani 1 1 d . B .
H1O2 H -0.4309 0.5199 0.4511 0.045 Uiso 1 1 d R . .
O3 O 0.0505(3) 0.39430(11) 0.00735(10) 0.0311(4) Uani 1 1 d . . .
H1O3 H 0.0137 0.3501 -0.0171 0.037 Uiso 1 1 d R . .
O4 O 0.0889(3) 0.26390(9) 0.10448(10) 0.0272(4) Uani 1 1 d . . .
H1O4 H 0.1841 0.2232 0.1042 0.033 Uiso 1 1 d R . .
O5 O 0.5999(3) 0.25120(10) 0.08973(10) 0.0328(4) Uani 1 1 d . . .
H1O5 H 0.7496 0.2551 0.0942 0.039 Uiso 1 1 d R . .
C1 C 0.1191(4) 0.38395(13) 0.18868(12) 0.0197(4) Uani 1 1 d . . .
H1A H -0.0471 0.3937 0.1679 0.024 Uiso 1 1 calc R . .
C2 C 0.0888(5) 0.33839(14) 0.26937(13) 0.0260(5) Uani 1 1 d . . .
H2A H 0.0394 0.2799 0.2593 0.031 Uiso 1 1 calc R . .
H2B H 0.2441 0.3374 0.2984 0.031 Uiso 1 1 calc R . .
C3 C -0.1000(5) 0.38182(14) 0.32163(13) 0.0255(5) Uani 1 1 d . . .
H3A H -0.2624 0.3671 0.3020 0.031 Uiso 1 1 calc R . .
H3B H -0.0855 0.3623 0.3782 0.031 Uiso 1 1 calc R . .
C4 C -0.0675(5) 0.47503(14) 0.31863(13) 0.0240(5) Uani 1 1 d . B .
C5 C 0.0825(4) 0.51375(13) 0.26816(13) 0.0252(5) Uani 1 1 d . . .
H5A H 0.0997 0.5726 0.2736 0.030 Uiso 1 1 calc R . .
C6 C 0.2264(4) 0.47112(13) 0.20324(12) 0.0216(4) Uani 1 1 d . . .
H6A H 0.3950 0.4643 0.2229 0.026 Uiso 1 1 calc R . .
C7 C 0.2316(5) 0.52054(13) 0.12253(13) 0.0233(5) Uani 1 1 d . C .
H7A H 0.0633 0.5213 0.1015 0.028 Uiso 1 1 calc R . .
C8 C 0.3807(4) 0.47026(14) 0.06193(13) 0.0254(5) Uani 1 1 d . . .
H8A H 0.3895 0.5016 0.0104 0.031 Uiso 1 1 calc R . .
H8B H 0.5462 0.4644 0.0830 0.031 Uiso 1 1 calc R . .
C9 C 0.2791(4) 0.38385(14) 0.04536(13) 0.0244(5) Uani 1 1 d . . .
H9A H 0.3890 0.3533 0.0078 0.029 Uiso 1 1 calc R . .
C10 C 0.2471(4) 0.33205(13) 0.12343(12) 0.0199(4) Uani 1 1 d . . .
C11 C -0.2148(5) 0.52830(15) 0.37316(14) 0.0299(5) Uani 1 1 d D . .
C12 C 0.3127(5) 0.61304(15) 0.12938(16) 0.0339(6) Uani 1 1 d D . .
H12A H 0.2252 0.6410 0.1747 0.041 Uiso 1 1 calc R A 1
C13 C 0.2657(8) 0.66005(18) 0.05018(19) 0.0568(10) Uani 1 1 d . C .
H13A H 0.2962 0.7198 0.0582 0.085 Uiso 1 1 calc R . .
H13B H 0.0983 0.6518 0.0338 0.085 Uiso 1 1 calc R . .
H13C H 0.3726 0.6386 0.0080 0.085 Uiso 1 1 calc R . .
C15 C 0.4875(4) 0.29772(15) 0.15231(13) 0.0244(5) Uani 1 1 d . . .
H15A H 0.5930 0.3445 0.1688 0.029 Uiso 1 1 calc R . .
H15B H 0.4620 0.2613 0.1999 0.029 Uiso 1 1 calc R . .
O1 O -0.229(5) 0.6045(3) 0.3659(16) 0.041(3) Uani 0.55(8) 1 d PDU B 1
C14 C 0.5828(17) 0.6225(18) 0.1414(19) 0.050(4) Uani 0.38(6) 1 d PDU C 1
H14A H 0.6655 0.6115 0.0902 0.075 Uiso 0.38(6) 1 calc PR C 1
H14B H 0.6378 0.5827 0.1823 0.075 Uiso 0.38(6) 1 calc PR C 1
H14C H 0.6187 0.6796 0.1593 0.075 Uiso 0.38(6) 1 calc PR C 1
O1' O -0.174(4) 0.6021(6) 0.3849(15) 0.034(3) Uani 0.45(8) 1 d PDU B 2
C14' C 0.5646(17) 0.6227(9) 0.1645(14) 0.047(3) Uani 0.62(6) 1 d PDU C 2
H14D H 0.6779 0.5890 0.1330 0.070 Uiso 0.62(6) 1 calc PR C 2
H14E H 0.5651 0.6038 0.2208 0.070 Uiso 0.62(6) 1 calc PR C 2
H14F H 0.6125 0.6817 0.1622 0.070 Uiso 0.62(6) 1 calc PR C 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C11 1.318(3) . ?
O2 H1O2 0.8400 . ?
O3 C9 1.430(3) . ?
O3 H1O3 0.8400 . ?
O4 C10 1.436(3) . ?
O4 H1O4 0.8400 . ?
O5 C15 1.420(3) . ?
O5 H1O5 0.8400 . ?
C1 C2 1.530(3) . ?
C1 C6 1.536(3) . ?
C1 C10 1.537(3) . ?
C1 H1A 1.0000 . ?
C2 C3 1.529(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.503(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.334(3) . ?
C4 C11 1.488(3) . ?
C5 C6 1.504(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.552(3) . ?
C6 H6A 1.0000 . ?
C7 C8 1.530(3) . ?
C7 C12 1.551(3) . ?
C7 H7A 1.0000 . ?
C8 C9 1.518(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.545(3) . ?
C9 H9A 1.0000 . ?
C10 C15 1.524(3) . ?
C11 O1' 1.219(7) . ?
C11 O1 1.228(6) . ?
C12 C14 1.525(8) . ?
C12 C14' 1.527(6) . ?
C12 C13 1.534(4) . ?
C12 H12A 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14' H14D 0.9800 . ?
C14' H14E 0.9800 . ?
C14' H14F 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
C11 O2 H1O2 108.0 . . ?
C9 O3 H1O3 109.3 . . ?
C10 O4 H1O4 101.7 . . ?
C15 O5 H1O5 109.5 . . ?
C2 C1 C6 109.78(17) . . ?
C2 C1 C10 114.00(17) . . ?
C6 C1 C10 114.83(18) . . ?
C2 C1 H1A 105.8 . . ?
C6 C1 H1A 105.8 . . ?
C10 C1 H1A 105.8 . . ?
C3 C2 C1 110.68(18) . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 110.45(19) . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C11 117.3(2) . . ?
C5 C4 C3 123.8(2) . . ?
C11 C4 C3 118.8(2) . . ?
C4 C5 C6 124.8(2) . . ?
C4 C5 H5A 117.6 . . ?
C6 C5 H5A 117.6 . . ?
C5 C6 C1 108.43(18) . . ?
C5 C6 C7 113.19(18) . . ?
C1 C6 C7 109.54(17) . . ?
C5 C6 H6A 108.5 . . ?
C1 C6 H6A 108.5 . . ?
C7 C6 H6A 108.5 . . ?
C8 C7 C12 113.02(19) . . ?
C8 C7 C6 107.85(17) . . ?
C12 C7 C6 115.35(18) . . ?
C8 C7 H7A 106.7 . . ?
C12 C7 H7A 106.7 . . ?
C6 C7 H7A 106.7 . . ?
C9 C8 C7 113.23(19) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
O3 C9 C8 107.75(19) . . ?
O3 C9 C10 109.14(19) . . ?
C8 C9 C10 112.34(17) . . ?
O3 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
O4 C10 C15 109.52(17) . . ?
O4 C10 C1 106.17(17) . . ?
C15 C10 C1 112.45(17) . . ?
O4 C10 C9 107.17(17) . . ?
C15 C10 C9 110.74(19) . . ?
C1 C10 C9 110.55(17) . . ?
O1' C11 O1 20.7(8) . . ?
O1' C11 O2 121.5(8) . . ?
O1 C11 O2 121.9(7) . . ?
O1' C11 C4 123.3(8) . . ?
O1 C11 C4 123.0(7) . . ?
O2 C11 C4 113.9(2) . . ?
C14 C12 C14' 14.9(10) . . ?
C14 C12 C13 103.3(10) . . ?
C14' C12 C13 115.6(9) . . ?
C14 C12 C7 113.1(11) . . ?
C14' C12 C7 113.1(6) . . ?
C13 C12 C7 110.8(2) . . ?
C14 C12 H12A 109.8 . . ?
C14' C12 H12A 96.7 . . ?
C13 C12 H12A 109.8 . . ?
C7 C12 H12A 109.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C15 C10 110.32(18) . . ?
O5 C15 H15A 109.6 . . ?
C10 C15 H15A 109.6 . . ?
O5 C15 H15B 109.6 . . ?
C10 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
C12 C14' H14D 109.5 . . ?
C12 C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
C12 C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 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 C1 C2 C3 66.3(2) . . . . ?
C10 C1 C2 C3 -163.21(19) . . . . ?
C1 C2 C3 C4 -43.3(3) . . . . ?
C2 C3 C4 C5 9.0(3) . . . . ?
C2 C3 C4 C11 -172.8(2) . . . . ?
C11 C4 C5 C6 -173.5(2) . . . . ?
C3 C4 C5 C6 4.7(4) . . . . ?
C4 C5 C6 C1 16.4(3) . . . . ?
C4 C5 C6 C7 138.1(2) . . . . ?
C2 C1 C6 C5 -50.1(2) . . . . ?
C10 C1 C6 C5 179.95(18) . . . . ?
C2 C1 C6 C7 -174.03(19) . . . . ?
C10 C1 C6 C7 56.0(2) . . . . ?
C5 C6 C7 C8 -179.45(19) . . . . ?
C1 C6 C7 C8 -58.3(2) . . . . ?
C5 C6 C7 C12 53.2(3) . . . . ?
C1 C6 C7 C12 174.31(19) . . . . ?
C12 C7 C8 C9 -171.2(2) . . . . ?
C6 C7 C8 C9 60.1(2) . . . . ?
C7 C8 C9 O3 64.5(2) . . . . ?
C7 C8 C9 C10 -55.7(3) . . . . ?
C2 C1 C10 O4 66.3(2) . . . . ?
C6 C1 C10 O4 -165.76(17) . . . . ?
C2 C1 C10 C15 -53.4(3) . . . . ?
C6 C1 C10 C15 74.5(2) . . . . ?
C2 C1 C10 C9 -177.75(19) . . . . ?
C6 C1 C10 C9 -49.9(2) . . . . ?
O3 C9 C10 O4 43.9(2) . . . . ?
C8 C9 C10 O4 163.34(18) . . . . ?
O3 C9 C10 C15 163.30(17) . . . . ?
C8 C9 C10 C15 -77.3(2) . . . . ?
O3 C9 C10 C1 -71.4(2) . . . . ?
C8 C9 C10 C1 48.1(3) . . . . ?
C5 C4 C11 O1' -14.4(18) . . . . ?
C3 C4 C11 O1' 167.2(18) . . . . ?
C5 C4 C11 O1 10(2) . . . . ?
C3 C4 C11 O1 -168(2) . . . . ?
C5 C4 C11 O2 178.6(2) . . . . ?
C3 C4 C11 O2 0.3(3) . . . . ?
C8 C7 C12 C14 -49.4(13) . . . . ?
C6 C7 C12 C14 75.3(13) . . . . ?
C8 C7 C12 C14' -65.6(10) . . . . ?
C6 C7 C12 C14' 59.1(10) . . . . ?
C8 C7 C12 C13 66.1(3) . . . . ?
C6 C7 C12 C13 -169.2(2) . . . . ?
O4 C10 C15 O5 62.9(2) . . . . ?
C1 C10 C15 O5 -179.28(18) . . . . ?
C9 C10 C15 O5 -55.1(2) . . . . ?

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
O2 H1O2 O3 0.84 1.79 2.619(2) 170.2 2_465
O3 H1O3 O5 0.84 2.07 2.841(2) 151.7 4_455
O4 H1O4 O1 0.84 1.98 2.710(14) 145.4 3_545
O4 H1O4 O1' 0.84 1.94 2.636(7) 138.8 3_545
O4 H1O4 O5 0.84 2.37 2.864(3) 118.0 .
O5 H1O5 O4 0.84 1.90 2.743(3) 179.9 1_655

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.042


####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 861574'
_audit_update_record             
;
2012-01-09 deposited with the CCDC.
2016-11-09 downloaded from the CCDC.
;
#TrackingRef 'a.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C15 H22 O3), H2 O'
_chemical_formula_sum            'C30 H46 O7'
_chemical_formula_weight         518.67
_chemical_absolute_configuration unk

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   16.315(3)
_cell_length_b                   17.050(3)
_cell_length_c                   5.2386(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1457.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    426
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.48

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             564
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9837
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'


_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12011
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         27.47
_reflns_number_total             1929
_reflns_number_gt                1892
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0445P)²+0.3946P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.2(16)
_refine_ls_number_reflns         1929
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1W O 0.0000 0.0000 0.2252(5) 0.0352(5) Uani 1 2 d S . .
H1WB H -0.0327 0.0326 0.1269 0.042 Uiso 1 1 d R . .
O1 O 0.06479(9) 0.13765(9) 0.3940(4) 0.0373(4) Uani 1 1 d . . .
H1A H 0.0589 0.0893 0.3696 0.056 Uiso 1 1 d R . .
O2 O 0.45933(9) 0.27234(9) -0.1573(3) 0.0369(4) Uani 1 1 d . . .
H2C H 0.4923 0.3031 -0.2292 0.055 Uiso 1 1 calc R . .
O3 O 0.41564(10) 0.38282(9) 0.0268(4) 0.0440(5) Uani 1 1 d . . .
C1 C 0.24641(11) 0.16201(10) 0.4157(4) 0.0238(4) Uani 1 1 d . . .
H1B H 0.2174 0.1597 0.2477 0.029 Uiso 1 1 calc R . .
C2 C 0.33268(12) 0.13082(11) 0.3711(4) 0.0279(4) Uani 1 1 d . . .
H2A H 0.3664 0.1395 0.5256 0.033 Uiso 1 1 calc R . .
H2B H 0.3304 0.0737 0.3379 0.033 Uiso 1 1 calc R . .
C3 C 0.37159(12) 0.17240(12) 0.1444(4) 0.0292(4) Uani 1 1 d . . .
H3A H 0.4305 0.1589 0.1355 0.035 Uiso 1 1 calc R . .
H3B H 0.3453 0.1543 -0.0154 0.035 Uiso 1 1 calc R . .
C4 C 0.36210(12) 0.26016(11) 0.1679(4) 0.0256(4) Uani 1 1 d . . .
C5 C 0.30892(11) 0.29347(11) 0.3278(4) 0.0254(4) Uani 1 1 d . . .
H5A H 0.3084 0.3491 0.3374 0.031 Uiso 1 1 calc R . .
C6 C 0.24978(12) 0.24923(11) 0.4938(5) 0.0225(4) Uani 1 1 d . . .
H6A H 0.2709 0.2517 0.6729 0.027 Uiso 1 1 calc R . .
C7 C 0.16205(11) 0.28402(11) 0.4939(4) 0.0231(4) Uani 1 1 d . . .
H7A H 0.1386 0.2750 0.3200 0.028 Uiso 1 1 calc R . .
C8 C 0.10982(13) 0.23681(12) 0.6823(4) 0.0286(4) Uani 1 1 d . . .
H8A H 0.1310 0.2456 0.8571 0.034 Uiso 1 1 calc R . .
H8B H 0.0529 0.2567 0.6765 0.034 Uiso 1 1 calc R . .
C9 C 0.10893(13) 0.14915(12) 0.6290(5) 0.0289(5) Uani 1 1 d . . .
H9A H 0.0800 0.1213 0.7708 0.035 Uiso 1 1 calc R . .
C10 C 0.19467(12) 0.11731(11) 0.6031(4) 0.0257(4) Uani 1 1 d . . .
C11 C 0.41435(12) 0.31176(12) 0.0083(4) 0.0285(4) Uani 1 1 d . . .
C12 C 0.15801(13) 0.37325(11) 0.5452(4) 0.0275(4) Uani 1 1 d . . .
H12A H 0.1941 0.3988 0.4153 0.033 Uiso 1 1 calc R . .
C13 C 0.07203(15) 0.40528(13) 0.5021(7) 0.0465(7) Uani 1 1 d . . .
H13A H 0.0738 0.4627 0.4994 0.070 Uiso 1 1 calc R . .
H13C H 0.0360 0.3877 0.6404 0.070 Uiso 1 1 calc R . .
H13D H 0.0509 0.3860 0.3386 0.070 Uiso 1 1 calc R . .
C14 C 0.1915(2) 0.39637(14) 0.8052(5) 0.0514(7) Uani 1 1 d . . .
H14C H 0.1885 0.4535 0.8247 0.077 Uiso 1 1 calc R . .
H14D H 0.2487 0.3794 0.8193 0.077 Uiso 1 1 calc R . .
H14A H 0.1588 0.3712 0.9392 0.077 Uiso 1 1 calc R . .
C15 C 0.21911(15) 0.05623(12) 0.7392(5) 0.0354(5) Uani 1 1 d . . .
H15A H 0.2736 0.0372 0.7224 0.042 Uiso 1 1 calc R . .
H15B H 0.1822 0.0314 0.8537 0.042 Uiso 1 1 calc R . .


_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
O1W H1WB 0.9270 . ?
O1 C9 1.440(3) . ?
O1 H1A 0.8400 . ?
O2 C11 1.320(3) . ?
O2 H2C 0.8400 . ?
O3 C11 1.216(3) . ?
C1 C10 1.502(3) . ?
C1 C2 1.523(3) . ?
C1 C6 1.543(3) . ?
C1 H1B 1.0000 . ?
C2 C3 1.522(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.509(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.333(3) . ?
C4 C11 1.483(3) . ?
C5 C6 1.502(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.549(3) . ?
C6 H6A 1.0000 . ?
C7 C8 1.532(3) . ?
C7 C12 1.546(3) . ?
C7 H7A 1.0000 . ?
C8 C9 1.520(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.507(3) . ?
C9 H9A 1.0000 . ?
C10 C15 1.324(3) . ?
C12 C14 1.519(3) . ?
C12 C13 1.522(3) . ?
C12 H12A 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13C 0.9800 . ?
C13 H13D 0.9800 . ?
C14 H14C 0.9800 . ?
C14 H14D 0.9800 . ?
C14 H14A 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
C9 O1 H1A 108.7 . . ?
C11 O2 H2C 109.5 . . ?
C10 C1 C2 116.25(16) . . ?
C10 C1 C6 109.60(16) . . ?
C2 C1 C6 110.14(15) . . ?
C10 C1 H1B 106.8 . . ?
C2 C1 H1B 106.8 . . ?
C6 C1 H1B 106.8 . . ?
C3 C2 C1 110.03(16) . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C4 C3 C2 110.80(18) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C11 118.39(18) . . ?
C5 C4 C3 122.73(19) . . ?
C11 C4 C3 118.88(19) . . ?
C4 C5 C6 124.61(18) . . ?
C4 C5 H5A 117.7 . . ?
C6 C5 H5A 117.7 . . ?
C5 C6 C1 110.68(17) . . ?
C5 C6 C7 113.68(16) . . ?
C1 C6 C7 109.64(15) . . ?
C5 C6 H6A 107.5 . . ?
C1 C6 H6A 107.5 . . ?
C7 C6 H6A 107.5 . . ?
C8 C7 C12 112.42(17) . . ?
C8 C7 C6 108.24(15) . . ?
C12 C7 C6 114.59(16) . . ?
C8 C7 H7A 107.1 . . ?
C12 C7 H7A 107.1 . . ?
C6 C7 H7A 107.1 . . ?
C9 C8 C7 113.80(18) . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
O1 C9 C10 109.77(18) . . ?
O1 C9 C8 107.21(17) . . ?
C10 C9 C8 111.21(17) . . ?
O1 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C15 C10 C1 125.58(19) . . ?
C15 C10 C9 121.0(2) . . ?
C1 C10 C9 113.44(16) . . ?
O3 C11 O2 123.4(2) . . ?
O3 C11 C4 123.8(2) . . ?
O2 C11 C4 112.82(18) . . ?
C14 C12 C13 111.8(2) . . ?
C14 C12 C7 113.30(18) . . ?
C13 C12 C7 111.49(18) . . ?
C14 C12 H12A 106.6 . . ?
C13 C12 H12A 106.6 . . ?
C7 C12 H12A 106.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
C12 C13 H13D 109.5 . . ?
H13A C13 H13D 109.5 . . ?
H13C C13 H13D 109.5 . . ?
C12 C14 H14C 109.5 . . ?
C12 C14 H14D 109.5 . . ?
H14C C14 H14D 109.5 . . ?
C12 C14 H14A 109.5 . . ?
H14C C14 H14A 109.5 . . ?
H14D C14 H14A 109.5 . . ?
C10 C15 H15A 120.0 . . ?
C10 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
C10 C1 C2 C3 169.73(17) . . . . ?
C6 C1 C2 C3 -64.9(2) . . . . ?
C1 C2 C3 C4 49.1(2) . . . . ?
C2 C3 C4 C5 -16.2(3) . . . . ?
C2 C3 C4 C11 163.41(18) . . . . ?
C11 C4 C5 C6 177.52(19) . . . . ?
C3 C4 C5 C6 -2.9(3) . . . . ?
C4 C5 C6 C1 -11.5(3) . . . . ?
C4 C5 C6 C7 -135.4(2) . . . . ?
C10 C1 C6 C5 173.39(16) . . . . ?
C2 C1 C6 C5 44.3(2) . . . . ?
C10 C1 C6 C7 -60.4(2) . . . . ?
C2 C1 C6 C7 170.48(17) . . . . ?
C5 C6 C7 C8 -176.52(17) . . . . ?
C1 C6 C7 C8 59.0(2) . . . . ?
C5 C6 C7 C12 -50.2(2) . . . . ?
C1 C6 C7 C12 -174.65(18) . . . . ?
C12 C7 C8 C9 177.04(18) . . . . ?
C6 C7 C8 C9 -55.4(2) . . . . ?
C7 C8 C9 O1 -68.5(2) . . . . ?
C7 C8 C9 C10 51.5(2) . . . . ?
C2 C1 C10 C15 3.4(3) . . . . ?
C6 C1 C10 C15 -122.3(2) . . . . ?
C2 C1 C10 C9 -177.39(17) . . . . ?
C6 C1 C10 C9 56.9(2) . . . . ?
O1 C9 C10 C15 -114.1(2) . . . . ?
C8 C9 C10 C15 127.4(2) . . . . ?
O1 C9 C10 C1 66.6(2) . . . . ?
C8 C9 C10 C1 -51.9(2) . . . . ?
C5 C4 C11 O3 5.3(3) . . . . ?
C3 C4 C11 O3 -174.4(2) . . . . ?
C5 C4 C11 O2 -174.55(18) . . . . ?
C3 C4 C11 O2 5.8(3) . . . . ?
C8 C7 C12 C14 62.5(2) . . . . ?
C6 C7 C12 C14 -61.6(3) . . . . ?
C8 C7 C12 C13 -64.7(2) . . . . ?
C6 C7 C12 C13 171.2(2) . . . . ?

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
O1W H1WB O3 0.93 1.85 2.762(2) 165.7 4_455
O1 H1A O1W 0.84 1.95 2.7216(17) 151.7 .
O2 H2C O1 0.84 1.78 2.618(2) 176.0 4

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.036


