# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_caesalmin_I
_database_code_depnum_ccdc_archive 'CCDC 1033413'
_audit_update_record             
;
2015-03-31 deposited with the CCDC.
2015-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H30 O8'
_chemical_formula_weight         434.47

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P21 21 21'

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                   7.6369(3)
_cell_length_b                   9.8408(4)
_cell_length_c                   28.3369(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2129.61(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2630
_cell_measurement_theta_min      3.1165
_cell_measurement_theta_max      60.7236

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.57019
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5787
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         60.81
_reflns_number_total             2860
_reflns_number_gt                2654
_reflns_threshold_expression     >2sigma(I)

_chemical_absolute_configuration rm

_computing_data_collection       'CrysAlis PRO '
_computing_cell_refinement       'CrysAlis PRO '
_computing_data_reduction        'CrysAlis PRO'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'XP (Sheldrick, 2008)'

_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)+(0.0478P)²+0.1940P] 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   0.1(2)
_refine_ls_number_reflns         2860
_refine_ls_number_parameters     287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0891
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
O1 O 1.0059(2) 0.34963(13) 0.11919(5) 0.0481(4) Uani 1 1 d . . .
O2 O 1.0913(3) 0.47970(18) 0.18000(6) 0.0739(5) Uani 1 1 d . . .
O3 O 0.98622(19) 0.10363(14) 0.07141(5) 0.0451(3) Uani 1 1 d . . .
H3 H 1.0195 0.1820 0.0753 0.068 Uiso 1 1 calc R . .
O4 O 0.8065(2) -0.14330(14) 0.05936(5) 0.0518(4) Uani 1 1 d . . .
O5 O 0.5735(3) -0.2658(2) 0.08177(8) 0.0899(6) Uani 1 1 d . . .
O6 O 0.9450(3) -0.26983(15) 0.13497(7) 0.0737(5) Uani 1 1 d . . .
H6 H 1.0125 -0.2998 0.1549 0.111 Uiso 1 1 calc R . .
O7 O 1.2516(3) -0.21871(19) 0.18344(8) 0.0900(7) Uani 1 1 d . . .
O8 O 1.3006(3) 0.16512(18) 0.27293(6) 0.0748(5) Uani 1 1 d . . .
C1 C 0.8452(3) 0.3062(2) 0.14336(7) 0.0485(5) Uani 1 1 d . . .
H1 H 0.8431 0.3457 0.1751 0.058 Uiso 1 1 calc R . .
C2 C 0.6948(3) 0.3631(2) 0.11522(8) 0.0584(6) Uani 1 1 d . . .
H2A H 0.7083 0.4608 0.1124 0.070 Uiso 1 1 calc R . .
H2B H 0.5859 0.3454 0.1317 0.070 Uiso 1 1 calc R . .
C3 C 0.6865(4) 0.3003(2) 0.06626(8) 0.0583(6) Uani 1 1 d . . .
H3A H 0.7909 0.3263 0.0490 0.070 Uiso 1 1 calc R . .
H3B H 0.5865 0.3381 0.0497 0.070 Uiso 1 1 calc R . .
C4 C 0.6714(3) 0.1433(2) 0.06567(8) 0.0518(5) Uani 1 1 d . . .
C5 C 0.8247(3) 0.0827(2) 0.09656(7) 0.0423(5) Uani 1 1 d . . .
C6 C 0.8162(3) -0.0730(2) 0.10411(7) 0.0440(5) Uani 1 1 d . . .
H6A H 0.7131 -0.0955 0.1231 0.053 Uiso 1 1 calc R . .
C7 C 0.9786(3) -0.12773(19) 0.12799(8) 0.0496(5) Uani 1 1 d . . .
H7 H 1.0792 -0.1168 0.1069 0.059 Uiso 1 1 calc R . .
C8 C 1.0178(3) -0.05818(19) 0.17504(7) 0.0460(5) Uani 1 1 d . . .
H8 H 0.9254 -0.0850 0.1972 0.055 Uiso 1 1 calc R . .
C9 C 1.0121(3) 0.0991(2) 0.17087(6) 0.0429(5) Uani 1 1 d . . .
H9 H 1.1091 0.1262 0.1503 0.052 Uiso 1 1 calc R . .
C10 C 0.8415(3) 0.1490(2) 0.14744(7) 0.0438(5) Uani 1 1 d . . .
C11 C 1.0463(3) 0.1631(2) 0.21977(7) 0.0569(6) Uani 1 1 d . . .
H11A H 1.0624 0.2605 0.2166 0.068 Uiso 1 1 calc R . .
H11B H 0.9470 0.1471 0.2404 0.068 Uiso 1 1 calc R . .
C12 C 1.2041(4) 0.1012(2) 0.23973(7) 0.0565(6) Uani 1 1 d . . .
C13 C 1.2742(3) -0.0228(2) 0.22967(8) 0.0545(6) Uani 1 1 d . . .
C14 C 1.1906(3) -0.1090(2) 0.19510(8) 0.0557(6) Uani 1 1 d . . .
C15 C 1.4257(4) -0.0367(3) 0.25926(9) 0.0664(7) Uani 1 1 d . . .
H15 H 1.5016 -0.1105 0.2605 0.080 Uiso 1 1 calc R . .
C16 C 1.4357(4) 0.0769(3) 0.28445(10) 0.0772(8) Uani 1 1 d . . .
H16 H 1.5218 0.0949 0.3068 0.093 Uiso 1 1 calc R . .
C18 C 0.4855(3) 0.1007(3) 0.08016(10) 0.0688(7) Uani 1 1 d . . .
H18A H 0.4052 0.1225 0.0552 0.103 Uiso 1 1 calc R . .
H18B H 0.4522 0.1485 0.1083 0.103 Uiso 1 1 calc R . .
H18C H 0.4830 0.0047 0.0860 0.103 Uiso 1 1 calc R . .
C19 C 0.6921(4) 0.1027(3) 0.01314(8) 0.0652(7) Uani 1 1 d . . .
H19A H 0.6246 0.1633 -0.0062 0.098 Uiso 1 1 calc R . .
H19B H 0.6511 0.0113 0.0087 0.098 Uiso 1 1 calc R . .
H19C H 0.8132 0.1082 0.0043 0.098 Uiso 1 1 calc R . .
C20 C 0.6855(3) 0.1155(2) 0.18007(8) 0.0568(6) Uani 1 1 d . . .
H20A H 0.6837 0.0197 0.1864 0.085 Uiso 1 1 calc R . .
H20B H 0.5782 0.1415 0.1649 0.085 Uiso 1 1 calc R . .
H20C H 0.6976 0.1645 0.2092 0.085 Uiso 1 1 calc R . .
C21 C 1.1102(3) 0.4429(2) 0.13981(8) 0.0506(6) Uani 1 1 d . . .
C22 C 1.2429(3) 0.4954(3) 0.10676(9) 0.0637(7) Uani 1 1 d . . .
H22A H 1.1866 0.5485 0.0827 0.096 Uiso 1 1 calc R . .
H22B H 1.3036 0.4206 0.0924 0.096 Uiso 1 1 calc R . .
H22C H 1.3249 0.5512 0.1236 0.096 Uiso 1 1 calc R . .
C23 C 0.6877(4) -0.2439(2) 0.05433(10) 0.0630(6) Uani 1 1 d . . .
C24 C 0.7185(5) -0.3209(3) 0.00986(11) 0.0897(10) Uani 1 1 d . . .
H24A H 0.6143 -0.3697 0.0014 0.135 Uiso 1 1 calc R . .
H24B H 0.8129 -0.3840 0.0144 0.135 Uiso 1 1 calc R . .
H24C H 0.7483 -0.2588 -0.0150 0.135 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
O1 C21 1.349(3) . ?
O1 C1 1.469(3) . ?
O2 C21 1.204(3) . ?
O3 C5 1.440(2) . ?
O3 H3 0.8200 . ?
O4 C23 1.351(3) . ?
O4 C6 1.446(2) . ?
O5 C23 1.188(3) . ?
O6 C7 1.435(3) . ?
O6 H6 0.8200 . ?
O7 C14 1.222(3) . ?
O8 C12 1.350(3) . ?
O8 C16 1.388(4) . ?
C1 C2 1.506(3) . ?
C1 C10 1.552(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.520(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.549(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C18 1.536(3) . ?
C4 C19 1.550(3) . ?
C4 C5 1.578(3) . ?
C5 C6 1.549(3) . ?
C5 C10 1.588(3) . ?
C6 C7 1.512(3) . ?
C6 H6A 0.9800 . ?
C7 C8 1.528(3) . ?
C7 H7 0.9800 . ?
C8 C14 1.522(3) . ?
C8 C9 1.553(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.542(3) . ?
C9 C11 1.544(3) . ?
C9 H9 0.9800 . ?
C10 C20 1.544(3) . ?
C11 C12 1.464(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.363(4) . ?
C13 C15 1.435(3) . ?
C13 C14 1.444(3) . ?
C15 C16 1.329(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.473(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.489(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
C21 O1 C1 119.29(16) . . ?
C5 O3 H3 109.5 . . ?
C23 O4 C6 118.53(18) . . ?
C7 O6 H6 109.5 . . ?
C12 O8 C16 106.2(2) . . ?
O1 C1 C2 106.40(17) . . ?
O1 C1 C10 109.84(17) . . ?
C2 C1 C10 113.3(2) . . ?
O1 C1 H1 109.1 . . ?
C2 C1 H1 109.1 . . ?
C10 C1 H1 109.1 . . ?
C1 C2 C3 111.36(19) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C2 C3 C4 114.7(2) . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
C4 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C18 C4 C3 109.7(2) . . ?
C18 C4 C19 106.3(2) . . ?
C3 C4 C19 105.09(19) . . ?
C18 C4 C5 115.71(19) . . ?
C3 C4 C5 108.44(19) . . ?
C19 C4 C5 111.08(19) . . ?
O3 C5 C6 104.23(16) . . ?
O3 C5 C4 107.86(16) . . ?
C6 C5 C4 114.84(18) . . ?
O3 C5 C10 108.73(16) . . ?
C6 C5 C10 106.52(15) . . ?
C4 C5 C10 114.10(17) . . ?
O4 C6 C7 105.32(16) . . ?
O4 C6 C5 110.73(16) . . ?
C7 C6 C5 112.34(18) . . ?
O4 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
O6 C7 C6 105.18(18) . . ?
O6 C7 C8 110.54(18) . . ?
C6 C7 C8 113.04(17) . . ?
O6 C7 H7 109.3 . . ?
C6 C7 H7 109.3 . . ?
C8 C7 H7 109.3 . . ?
C14 C8 C7 110.39(18) . . ?
C14 C8 C9 112.32(19) . . ?
C7 C8 C9 111.99(16) . . ?
C14 C8 H8 107.3 . . ?
C7 C8 H8 107.3 . . ?
C9 C8 H8 107.3 . . ?
C10 C9 C11 113.51(17) . . ?
C10 C9 C8 111.94(18) . . ?
C11 C9 C8 109.51(16) . . ?
C10 C9 H9 107.2 . . ?
C11 C9 H9 107.2 . . ?
C8 C9 H9 107.2 . . ?
C9 C10 C20 109.03(16) . . ?
C9 C10 C1 109.53(18) . . ?
C20 C10 C1 105.73(18) . . ?
C9 C10 C5 109.19(16) . . ?
C20 C10 C5 113.18(17) . . ?
C1 C10 C5 110.10(16) . . ?
C12 C11 C9 108.40(19) . . ?
C12 C11 H11A 110.0 . . ?
C9 C11 H11A 110.0 . . ?
C12 C11 H11B 110.0 . . ?
C9 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
O8 C12 C13 110.4(2) . . ?
O8 C12 C11 121.6(2) . . ?
C13 C12 C11 128.0(2) . . ?
C12 C13 C15 106.2(2) . . ?
C12 C13 C14 119.6(2) . . ?
C15 C13 C14 134.1(2) . . ?
O7 C14 C13 122.3(2) . . ?
O7 C14 C8 121.3(2) . . ?
C13 C14 C8 116.4(2) . . ?
C16 C15 C13 106.3(3) . . ?
C16 C15 H15 126.9 . . ?
C13 C15 H15 126.9 . . ?
C15 C16 O8 110.9(2) . . ?
C15 C16 H16 124.5 . . ?
O8 C16 H16 124.5 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 O1 123.0(2) . . ?
O2 C21 C22 125.4(2) . . ?
O1 C21 C22 111.66(19) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5 C23 O4 123.8(2) . . ?
O5 C23 C24 125.3(3) . . ?
O4 C23 C24 110.9(2) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C21 O1 C1 C2 110.2(2) . . . . ?
C21 O1 C1 C10 -126.79(19) . . . . ?
O1 C1 C2 C3 65.2(2) . . . . ?
C10 C1 C2 C3 -55.6(3) . . . . ?
C1 C2 C3 C4 57.0(3) . . . . ?
C2 C3 C4 C18 74.0(3) . . . . ?
C2 C3 C4 C19 -172.1(2) . . . . ?
C2 C3 C4 C5 -53.2(3) . . . . ?
C18 C4 C5 O3 165.52(19) . . . . ?
C3 C4 C5 O3 -70.7(2) . . . . ?
C19 C4 C5 O3 44.3(2) . . . . ?
C18 C4 C5 C6 49.8(3) . . . . ?
C3 C4 C5 C6 173.57(19) . . . . ?
C19 C4 C5 C6 -71.4(2) . . . . ?
C18 C4 C5 C10 -73.6(2) . . . . ?
C3 C4 C5 C10 50.2(2) . . . . ?
C19 C4 C5 C10 165.17(18) . . . . ?
C23 O4 C6 C7 104.4(2) . . . . ?
C23 O4 C6 C5 -133.9(2) . . . . ?
O3 C5 C6 O4 -63.2(2) . . . . ?
C4 C5 C6 O4 54.6(2) . . . . ?
C10 C5 C6 O4 -178.09(16) . . . . ?
O3 C5 C6 C7 54.2(2) . . . . ?
C4 C5 C6 C7 172.01(17) . . . . ?
C10 C5 C6 C7 -60.6(2) . . . . ?
O4 C6 C7 O6 -63.0(2) . . . . ?
C5 C6 C7 O6 176.42(17) . . . . ?
O4 C6 C7 C8 176.35(16) . . . . ?
C5 C6 C7 C8 55.7(2) . . . . ?
O6 C7 C8 C14 67.3(2) . . . . ?
C6 C7 C8 C14 -175.09(17) . . . . ?
O6 C7 C8 C9 -166.7(2) . . . . ?
C6 C7 C8 C9 -49.1(3) . . . . ?
C14 C8 C9 C10 176.17(16) . . . . ?
C7 C8 C9 C10 51.3(2) . . . . ?
C14 C8 C9 C11 -57.0(2) . . . . ?
C7 C8 C9 C11 178.07(19) . . . . ?
C11 C9 C10 C20 -58.7(2) . . . . ?
C8 C9 C10 C20 65.9(2) . . . . ?
C11 C9 C10 C1 56.5(2) . . . . ?
C8 C9 C10 C1 -178.89(17) . . . . ?
C11 C9 C10 C5 177.15(16) . . . . ?
C8 C9 C10 C5 -58.3(2) . . . . ?
O1 C1 C10 C9 53.6(2) . . . . ?
C2 C1 C10 C9 172.47(17) . . . . ?
O1 C1 C10 C20 170.95(16) . . . . ?
C2 C1 C10 C20 -70.2(2) . . . . ?
O1 C1 C10 C5 -66.5(2) . . . . ?
C2 C1 C10 C5 52.4(2) . . . . ?
O3 C5 C10 C9 -50.4(2) . . . . ?
C6 C5 C10 C9 61.4(2) . . . . ?
C4 C5 C10 C9 -170.78(17) . . . . ?
O3 C5 C10 C20 -172.00(17) . . . . ?
C6 C5 C10 C20 -60.2(2) . . . . ?
C4 C5 C10 C20 67.6(2) . . . . ?
O3 C5 C10 C1 69.9(2) . . . . ?
C6 C5 C10 C1 -178.28(19) . . . . ?
C4 C5 C10 C1 -50.5(2) . . . . ?
C10 C9 C11 C12 176.09(17) . . . . ?
C8 C9 C11 C12 50.2(2) . . . . ?
C16 O8 C12 C13 -0.6(3) . . . . ?
C16 O8 C12 C11 178.5(2) . . . . ?
C9 C11 C12 O8 156.65(19) . . . . ?
C9 C11 C12 C13 -24.4(3) . . . . ?
O8 C12 C13 C15 0.3(3) . . . . ?
C11 C12 C13 C15 -178.7(2) . . . . ?
O8 C12 C13 C14 179.66(19) . . . . ?
C11 C12 C13 C14 0.6(4) . . . . ?
C12 C13 C14 O7 177.1(2) . . . . ?
C15 C13 C14 O7 -3.7(4) . . . . ?
C12 C13 C14 C8 -5.1(3) . . . . ?
C15 C13 C14 C8 174.1(2) . . . . ?
C7 C8 C14 O7 -22.7(3) . . . . ?
C9 C8 C14 O7 -148.5(2) . . . . ?
C7 C8 C14 C13 159.44(19) . . . . ?
C9 C8 C14 C13 33.7(3) . . . . ?
C12 C13 C15 C16 0.1(3) . . . . ?
C14 C13 C15 C16 -179.1(3) . . . . ?
C13 C15 C16 O8 -0.5(3) . . . . ?
C12 O8 C16 C15 0.6(3) . . . . ?
C1 O1 C21 O2 10.4(3) . . . . ?
C1 O1 C21 C22 -167.83(18) . . . . ?
C6 O4 C23 O5 11.3(4) . . . . ?
C6 O4 C23 C24 -169.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        60.81
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.105
_refine_diff_density_rms         0.028
####################################################################### 
# 
# 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_neocaesalpin_B
_database_code_depnum_ccdc_archive 'CCDC 1033414'
_audit_update_record             
;
2015-03-31 deposited with the CCDC.
2015-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H36 O9'
_chemical_formula_weight         468.53

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'

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

_cell_length_a                   6.7833(5)
_cell_length_b                   12.2913(7)
_cell_length_c                   14.6874(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.192(5)
_cell_angle_gamma                90.00
_cell_volume                     1201.28(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1630
_cell_measurement_theta_min      3.1165
_cell_measurement_theta_max      62.97

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4499
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         62.98
_reflns_number_total             2864
_reflns_number_gt                2668
_reflns_threshold_expression     >2sigma(I)

_chemical_absolute_configuration rm

_computing_data_collection       'CrysAlis PRO '
_computing_cell_refinement       'CrysAlis PRO '
_computing_data_reduction        'CrysAlis PRO'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'XP (Sheldrick, 2008)'

_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)+(0.0603P)²+0.7698P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_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   0.2(3)
_refine_ls_number_reflns         2864
_refine_ls_number_parameters     306
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1448
_refine_ls_wR_factor_gt          0.1198
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_restrained_S_all      1.188
_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
O1 O 0.5377(4) 0.7113(2) 0.63104(16) 0.0348(7) Uani 1 1 d . . .
O2 O 0.2842(5) 0.7695(3) 0.5201(2) 0.0575(9) Uani 1 1 d . . .
O3 O 0.2705(4) 0.5354(3) 0.59942(18) 0.0395(7) Uani 1 1 d . . .
O4 O -0.0355(5) 0.5884(4) 0.6185(2) 0.0702(12) Uani 1 1 d . . .
O5 O 0.8514(3) 0.6773(2) 0.78607(18) 0.0375(7) Uani 1 1 d . . .
H5 H 0.8109 0.6708 0.7300 0.056 Uiso 1 1 calc R . .
O6 O 0.3450(4) 1.1204(3) 0.7148(2) 0.0435(7) Uani 1 1 d . . .
O7 O 0.2299(5) 1.2638(3) 0.7818(3) 0.0626(9) Uani 1 1 d . . .
O8 O 0.6260(4) 1.0443(3) 0.67256(19) 0.0497(8) Uani 1 1 d . . .
H8 H 0.7005 1.0974 0.6813 0.075 Uiso 1 1 calc R . .
C1 C 0.4027(5) 0.6900(4) 0.6947(3) 0.0341(9) Uani 1 1 d . . .
H1 H 0.2780 0.7310 0.6744 0.041 Uiso 1 1 calc R . .
C2 C 0.3544(6) 0.5702(4) 0.6937(3) 0.0354(9) Uani 1 1 d . . .
H2 H 0.2568 0.5565 0.7336 0.043 Uiso 1 1 calc R . .
C3 C 0.5398(6) 0.5014(4) 0.7259(3) 0.0394(10) Uani 1 1 d . . .
H3A H 0.6327 0.5124 0.6842 0.047 Uiso 1 1 calc R . .
H3B H 0.5017 0.4253 0.7229 0.047 Uiso 1 1 calc R . .
C4 C 0.6471(6) 0.5291(4) 0.8260(3) 0.0398(10) Uani 1 1 d . . .
C5 C 0.6902(5) 0.6537(4) 0.8340(3) 0.0321(9) Uani 1 1 d . . .
C6 C 0.7763(6) 0.6916(4) 0.9333(3) 0.0386(10) Uani 1 1 d . . .
H6A H 0.6743 0.6835 0.9709 0.046 Uiso 1 1 calc R . .
H6B H 0.8890 0.6455 0.9597 0.046 Uiso 1 1 calc R . .
C7 C 0.8450(6) 0.8084(4) 0.9368(3) 0.0400(10) Uani 1 1 d . . .
H7A H 0.9628 0.8133 0.9087 0.048 Uiso 1 1 calc R . .
H7B H 0.8847 0.8300 1.0013 0.048 Uiso 1 1 calc R . .
C8 C 0.6863(5) 0.8886(4) 0.8876(3) 0.0329(9) Uani 1 1 d . . .
H8A H 0.5798 0.8914 0.9241 0.039 Uiso 1 1 calc R . .
C9 C 0.5866(5) 0.8484(4) 0.7884(3) 0.0302(8) Uani 1 1 d . . .
H9 H 0.6904 0.8471 0.7504 0.036 Uiso 1 1 calc R . .
C10 C 0.5064(5) 0.7305(4) 0.7933(2) 0.0314(9) Uani 1 1 d . . .
C11 C 0.4230(6) 0.9287(4) 0.7438(3) 0.0358(9) Uani 1 1 d . . .
H11A H 0.3648 0.9045 0.6815 0.043 Uiso 1 1 calc R . .
H11B H 0.3170 0.9305 0.7796 0.043 Uiso 1 1 calc R . .
C12 C 0.5087(6) 1.0412(4) 0.7397(3) 0.0377(9) Uani 1 1 d . . .
C13 C 0.6136(6) 1.0764(4) 0.8349(3) 0.0359(9) Uani 1 1 d . . .
C14 C 0.7731(6) 1.0045(4) 0.8874(3) 0.0365(9) Uani 1 1 d . . .
H14 H 0.8019 1.0301 0.9518 0.044 Uiso 1 1 calc R . .
C15 C 0.5224(6) 1.1649(4) 0.8593(3) 0.0403(10) Uani 1 1 d . . .
H15 H 0.5611 1.2029 0.9146 0.048 Uiso 1 1 calc R . .
C16 C 0.3524(6) 1.1928(4) 0.7856(3) 0.0434(10) Uani 1 1 d . . .
C17 C 0.9690(6) 1.0139(5) 0.8498(3) 0.0512(12) Uani 1 1 d . . .
H17A H 1.0765 0.9798 0.8924 0.077 Uiso 1 1 calc R . .
H17B H 1.0004 1.0893 0.8430 0.077 Uiso 1 1 calc R . .
H17C H 0.9524 0.9785 0.7905 0.077 Uiso 1 1 calc R . .
C18 C 0.8467(7) 0.4652(5) 0.8445(4) 0.0573(13) Uani 1 1 d . . .
H18A H 0.8189 0.3886 0.8410 0.086 Uiso 1 1 calc R . .
H18B H 0.9212 0.4828 0.9052 0.086 Uiso 1 1 calc R . .
H18C H 0.9243 0.4844 0.7987 0.086 Uiso 1 1 calc R . .
C19 C 0.5223(8) 0.4853(4) 0.8954(3) 0.0543(13) Uani 1 1 d . . .
H19A H 0.3922 0.5190 0.8836 0.081 Uiso 1 1 calc R . .
H19B H 0.5898 0.5017 0.9576 0.081 Uiso 1 1 calc R . .
H19C H 0.5073 0.4079 0.8883 0.081 Uiso 1 1 calc R . .
C20 C 0.3366(6) 0.7294(4) 0.8512(3) 0.0397(10) Uani 1 1 d . . .
H20A H 0.2324 0.7792 0.8244 0.060 Uiso 1 1 calc R . .
H20B H 0.3909 0.7509 0.9139 0.060 Uiso 1 1 calc R . .
H20C H 0.2818 0.6573 0.8510 0.060 Uiso 1 1 calc R . .
C21 C 0.4610(7) 0.7504(4) 0.5463(3) 0.0414(10) Uani 1 1 d . . .
C22 C 0.6199(8) 0.7677(6) 0.4911(3) 0.0655(15) Uani 1 1 d . . .
H22A H 0.7487 0.7509 0.5285 0.098 Uiso 1 1 calc R . .
H22B H 0.6183 0.8422 0.4714 0.098 Uiso 1 1 calc R . .
H22C H 0.5955 0.7211 0.4376 0.098 Uiso 1 1 calc R . .
C23 C 0.0703(6) 0.5495(4) 0.5706(3) 0.0439(11) Uani 1 1 d . . .
C24 C 0.0022(7) 0.5111(5) 0.4731(3) 0.0577(14) Uani 1 1 d . . .
H24A H 0.1109 0.5172 0.4402 0.087 Uiso 1 1 calc R . .
H24B H -0.1085 0.5551 0.4430 0.087 Uiso 1 1 calc R . .
H24C H -0.0397 0.4366 0.4734 0.087 Uiso 1 1 calc R . .
O1W O 0.8268(5) 0.2362(3) 0.6754(2) 0.0655(10) Uani 1 1 d . . .
H1W H 0.8120 0.2407 0.6160 0.098 Uiso 1 1 d R . .
H2W H 0.9459 0.2371 0.7065 0.098 Uiso 1 1 d 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
O1 C21 1.342(5) . ?
O1 C1 1.454(4) . ?
O2 C21 1.209(5) . ?
O3 C23 1.353(5) . ?
O3 C2 1.455(5) . ?
O4 C23 1.198(6) . ?
O5 C5 1.441(5) . ?
O5 H5 0.8200 . ?
O6 C16 1.363(5) . ?
O6 C12 1.468(5) . ?
O7 C16 1.199(6) . ?
O8 C12 1.383(5) . ?
O8 H8 0.8200 . ?
C1 C2 1.508(6) . ?
C1 C10 1.564(5) . ?
C1 H1 0.9800 . ?
C2 C3 1.514(6) . ?
C2 H2 0.9800 . ?
C3 C4 1.547(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C19 1.543(6) . ?
C4 C18 1.543(6) . ?
C4 C5 1.559(6) . ?
C5 C6 1.534(5) . ?
C5 C10 1.586(5) . ?
C6 C7 1.507(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.533(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C14 1.543(6) . ?
C8 C9 1.563(5) . ?
C8 H8A 0.9800 . ?
C9 C11 1.534(6) . ?
C9 C10 1.554(6) . ?
C9 H9 0.9800 . ?
C10 C20 1.559(5) . ?
C11 C12 1.506(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.504(6) . ?
C13 C15 1.334(6) . ?
C13 C14 1.490(6) . ?
C14 C17 1.539(6) . ?
C14 H14 0.9800 . ?
C15 C16 1.461(6) . ?
C15 H15 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.484(6) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.493(6) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
O1W H1W 0.8609 . ?
O1W H2W 0.8476 . ?

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
C21 O1 C1 118.8(3) . . ?
C23 O3 C2 116.3(3) . . ?
C5 O5 H5 109.5 . . ?
C16 O6 C12 109.2(3) . . ?
C12 O8 H8 109.5 . . ?
O1 C1 C2 109.4(3) . . ?
O1 C1 C10 108.2(3) . . ?
C2 C1 C10 112.2(3) . . ?
O1 C1 H1 109.0 . . ?
C2 C1 H1 109.0 . . ?
C10 C1 H1 109.0 . . ?
O3 C2 C1 109.9(3) . . ?
O3 C2 C3 106.3(3) . . ?
C1 C2 C3 112.1(3) . . ?
O3 C2 H2 109.5 . . ?
C1 C2 H2 109.5 . . ?
C3 C2 H2 109.5 . . ?
C2 C3 C4 112.5(4) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C19 C4 C18 106.4(4) . . ?
C19 C4 C3 109.5(4) . . ?
C18 C4 C3 106.9(4) . . ?
C19 C4 C5 114.3(4) . . ?
C18 C4 C5 110.0(4) . . ?
C3 C4 C5 109.5(3) . . ?
O5 C5 C6 102.6(3) . . ?
O5 C5 C4 108.1(3) . . ?
C6 C5 C4 113.7(3) . . ?
O5 C5 C10 108.1(3) . . ?
C6 C5 C10 107.7(3) . . ?
C4 C5 C10 115.8(3) . . ?
C7 C6 C5 112.3(4) . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 C8 114.3(3) . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 C14 111.2(3) . . ?
C7 C8 C9 111.9(3) . . ?
C14 C8 C9 112.7(3) . . ?
C7 C8 H8A 106.9 . . ?
C14 C8 H8A 106.9 . . ?
C9 C8 H8A 106.9 . . ?
C11 C9 C10 112.9(3) . . ?
C11 C9 C8 109.9(3) . . ?
C10 C9 C8 110.0(3) . . ?
C11 C9 H9 107.9 . . ?
C10 C9 H9 107.9 . . ?
C8 C9 H9 107.9 . . ?
C9 C10 C20 109.7(3) . . ?
C9 C10 C1 110.6(3) . . ?
C20 C10 C1 104.8(3) . . ?
C9 C10 C5 108.5(3) . . ?
C20 C10 C5 113.5(3) . . ?
C1 C10 C5 109.8(3) . . ?
C12 C11 C9 110.8(3) . . ?
C12 C11 H11A 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
O8 C12 O6 108.4(3) . . ?
O8 C12 C13 114.9(3) . . ?
O6 C12 C13 103.8(3) . . ?
O8 C12 C11 109.5(4) . . ?
O6 C12 C11 109.8(3) . . ?
C13 C12 C11 110.1(3) . . ?
C15 C13 C14 132.3(4) . . ?
C15 C13 C12 108.9(4) . . ?
C14 C13 C12 118.3(4) . . ?
C13 C14 C17 111.2(4) . . ?
C13 C14 C8 108.1(3) . . ?
C17 C14 C8 115.3(4) . . ?
C13 C14 H14 107.3 . . ?
C17 C14 H14 107.3 . . ?
C8 C14 H14 107.3 . . ?
C13 C15 C16 109.5(4) . . ?
C13 C15 H15 125.3 . . ?
C16 C15 H15 125.3 . . ?
O7 C16 O6 121.1(4) . . ?
O7 C16 C15 130.3(4) . . ?
O6 C16 C15 108.6(4) . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 O1 123.1(4) . . ?
O2 C21 C22 125.4(4) . . ?
O1 C21 C22 111.5(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C23 O3 123.1(4) . . ?
O4 C23 C24 125.4(4) . . ?
O3 C23 C24 111.4(4) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
H1W O1W H2W 117.1 . . ?

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
C21 O1 C1 C2 99.5(4) . . . . ?
C21 O1 C1 C10 -138.0(4) . . . . ?
C23 O3 C2 C1 -85.3(4) . . . . ?
C23 O3 C2 C3 153.2(4) . . . . ?
O1 C1 C2 O3 -56.2(4) . . . . ?
C10 C1 C2 O3 -176.3(3) . . . . ?
O1 C1 C2 C3 61.8(4) . . . . ?
C10 C1 C2 C3 -58.3(4) . . . . ?
O3 C2 C3 C4 180.0(3) . . . . ?
C1 C2 C3 C4 59.9(5) . . . . ?
C2 C3 C4 C19 72.9(5) . . . . ?
C2 C3 C4 C18 -172.3(4) . . . . ?
C2 C3 C4 C5 -53.2(5) . . . . ?
C19 C4 C5 O5 163.7(3) . . . . ?
C18 C4 C5 O5 44.2(4) . . . . ?
C3 C4 C5 O5 -73.0(4) . . . . ?
C19 C4 C5 C6 50.5(5) . . . . ?
C18 C4 C5 C6 -69.0(4) . . . . ?
C3 C4 C5 C6 173.9(3) . . . . ?
C19 C4 C5 C10 -74.9(4) . . . . ?
C18 C4 C5 C10 165.6(3) . . . . ?
C3 C4 C5 C10 48.4(4) . . . . ?
O5 C5 C6 C7 55.0(4) . . . . ?
C4 C5 C6 C7 171.4(3) . . . . ?
C10 C5 C6 C7 -58.9(4) . . . . ?
C5 C6 C7 C8 52.6(5) . . . . ?
C6 C7 C8 C14 -175.4(3) . . . . ?
C6 C7 C8 C9 -48.4(5) . . . . ?
C7 C8 C9 C11 177.6(3) . . . . ?
C14 C8 C9 C11 -56.2(4) . . . . ?
C7 C8 C9 C10 52.6(4) . . . . ?
C14 C8 C9 C10 178.9(3) . . . . ?
C11 C9 C10 C20 -59.3(4) . . . . ?
C8 C9 C10 C20 63.9(4) . . . . ?
C11 C9 C10 C1 55.7(4) . . . . ?
C8 C9 C10 C1 179.0(3) . . . . ?
C11 C9 C10 C5 176.2(3) . . . . ?
C8 C9 C10 C5 -60.6(3) . . . . ?
O1 C1 C10 C9 49.5(4) . . . . ?
C2 C1 C10 C9 170.3(3) . . . . ?
O1 C1 C10 C20 167.6(4) . . . . ?
C2 C1 C10 C20 -71.6(4) . . . . ?
O1 C1 C10 C5 -70.2(4) . . . . ?
C2 C1 C10 C5 50.6(4) . . . . ?
O5 C5 C10 C9 -46.9(4) . . . . ?
C6 C5 C10 C9 63.3(4) . . . . ?
C4 C5 C10 C9 -168.3(3) . . . . ?
O5 C5 C10 C20 -169.1(3) . . . . ?
C6 C5 C10 C20 -58.9(4) . . . . ?
C4 C5 C10 C20 69.5(4) . . . . ?
O5 C5 C10 C1 74.0(4) . . . . ?
C6 C5 C10 C1 -175.8(3) . . . . ?
C4 C5 C10 C1 -47.4(4) . . . . ?
C10 C9 C11 C12 -179.4(3) . . . . ?
C8 C9 C11 C12 57.3(4) . . . . ?
C16 O6 C12 O8 -122.5(4) . . . . ?
C16 O6 C12 C13 0.2(4) . . . . ?
C16 O6 C12 C11 117.9(4) . . . . ?
C9 C11 C12 O8 72.5(4) . . . . ?
C9 C11 C12 O6 -168.5(3) . . . . ?
C9 C11 C12 C13 -54.8(4) . . . . ?
O8 C12 C13 C15 117.3(4) . . . . ?
O6 C12 C13 C15 -1.0(4) . . . . ?
C11 C12 C13 C15 -118.5(4) . . . . ?
O8 C12 C13 C14 -69.8(5) . . . . ?
O6 C12 C13 C14 171.9(3) . . . . ?
C11 C12 C13 C14 54.4(4) . . . . ?
C15 C13 C14 C17 -113.0(5) . . . . ?
C12 C13 C14 C17 76.1(5) . . . . ?
C15 C13 C14 C8 119.5(5) . . . . ?
C12 C13 C14 C8 -51.4(4) . . . . ?
C7 C8 C14 C13 177.5(3) . . . . ?
C9 C8 C14 C13 50.9(4) . . . . ?
C7 C8 C14 C17 52.5(5) . . . . ?
C9 C8 C14 C17 -74.1(4) . . . . ?
C14 C13 C15 C16 -170.2(4) . . . . ?
C12 C13 C15 C16 1.4(5) . . . . ?
C12 O6 C16 O7 -178.2(4) . . . . ?
C12 O6 C16 C15 0.6(5) . . . . ?
C13 C15 C16 O7 177.4(5) . . . . ?
C13 C15 C16 O6 -1.3(5) . . . . ?
C1 O1 C21 O2 0.4(7) . . . . ?
C1 O1 C21 C22 179.7(4) . . . . ?
C2 O3 C23 O4 0.1(7) . . . . ?
C2 O3 C23 C24 179.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        62.98
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.042
