# 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_150522a
_database_code_depnum_ccdc_archive 'CCDC 1462858'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-12-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        sd310-42
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H32 O4'
_chemical_formula_weight         348.47

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   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                   8.8580(6)
_cell_length_b                   12.4336(7)
_cell_length_c                   17.5420(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1932.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    922
_cell_measurement_theta_min      4.9940
_cell_measurement_theta_max      52.0380

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7819
_exptl_absorpt_correction_T_max  0.8296
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3971
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0777
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.36
_diffrn_reflns_theta_max         66.14
_reflns_number_total             2860
_reflns_number_gt                1907
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0347P)²+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.0030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_number_reflns         2860
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.1105
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_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 0.2804(4) 0.4854(2) 0.31921(17) 0.0620(9) Uani 1 1 d . . .
H1 H 0.2345 0.5271 0.2914 0.093 Uiso 1 1 calc R . .
O2 O 0.1379(3) 0.2448(2) 0.22381(15) 0.0519(7) Uani 1 1 d . . .
O3 O 0.1713(3) 0.1985(2) 0.09556(15) 0.0578(8) Uani 1 1 d . . .
O4 O 0.0724(3) 0.6029(2) 0.21264(18) 0.0589(8) Uani 1 1 d . . .
H4 H 0.0033 0.6436 0.2243 0.088 Uiso 1 1 calc R . .
C1 C 0.4738(5) 0.2978(3) 0.0948(2) 0.0545(11) Uani 1 1 d . . .
H1A H 0.4318 0.2617 0.0507 0.065 Uiso 1 1 calc R . .
H1B H 0.5165 0.3655 0.0777 0.065 Uiso 1 1 calc R . .
C2 C 0.5995(5) 0.2286(4) 0.1279(3) 0.0651(14) Uani 1 1 d . . .
H2A H 0.6785 0.2192 0.0902 0.078 Uiso 1 1 calc R . .
H2B H 0.5599 0.1581 0.1408 0.078 Uiso 1 1 calc R . .
C3 C 0.6652(5) 0.2813(4) 0.1992(3) 0.0661(13) Uani 1 1 d . . .
H3A H 0.7075 0.3506 0.1855 0.079 Uiso 1 1 calc R . .
H3B H 0.7466 0.2368 0.2186 0.079 Uiso 1 1 calc R . .
C4 C 0.5467(5) 0.2973(3) 0.2626(3) 0.0550(11) Uani 1 1 d . . .
C5 C 0.4107(4) 0.3608(3) 0.2295(2) 0.0450(10) Uani 1 1 d . . .
H5 H 0.4512 0.4325 0.2187 0.054 Uiso 1 1 calc R . .
C6 C 0.2802(5) 0.3810(3) 0.2860(2) 0.0498(10) Uani 1 1 d . . .
H6 H 0.2898 0.3285 0.3275 0.060 Uiso 1 1 calc R . .
C7 C 0.1324(5) 0.3579(3) 0.2446(2) 0.0471(10) Uani 1 1 d . . .
H7 H 0.0458 0.3726 0.2777 0.057 Uiso 1 1 calc R . .
C8 C 0.1274(4) 0.4277(3) 0.1743(2) 0.0437(9) Uani 1 1 d . . .
C9 C 0.2383(5) 0.4091(3) 0.1257(2) 0.0420(9) Uani 1 1 d . . .
C10 C 0.3469(5) 0.3211(3) 0.1513(2) 0.0422(9) Uani 1 1 d . . .
C11 C 0.2544(5) 0.4678(3) 0.0511(2) 0.0505(11) Uani 1 1 d . . .
H11A H 0.2265 0.4199 0.0098 0.061 Uiso 1 1 calc R . .
H11B H 0.3593 0.4878 0.0440 0.061 Uiso 1 1 calc R . .
C12 C 0.1565(4) 0.5687(3) 0.0474(2) 0.0526(11) Uani 1 1 d . . .
H12A H 0.1467 0.5910 -0.0053 0.063 Uiso 1 1 calc R . .
H12B H 0.2063 0.6263 0.0750 0.063 Uiso 1 1 calc R . .
C13 C -0.0015(5) 0.5512(4) 0.0812(2) 0.0527(11) Uani 1 1 d . . .
C14 C 0.0145(5) 0.5171(3) 0.1658(2) 0.0488(10) Uani 1 1 d . . .
H14 H -0.0837 0.4937 0.1854 0.059 Uiso 1 1 calc R . .
C15 C -0.0942(6) 0.6546(4) 0.0777(3) 0.0740(15) Uani 1 1 d . . .
H15 H -0.1927 0.6497 0.0956 0.089 Uiso 1 1 calc R . .
C16 C -0.0525(7) 0.7493(5) 0.0525(3) 0.104(2) Uani 1 1 d . . .
H16A H 0.0447 0.7593 0.0338 0.124 Uiso 1 1 calc R . .
H16B H -0.1201 0.8065 0.0534 0.124 Uiso 1 1 calc R . .
C17 C 0.5088(6) 0.1886(4) 0.2988(3) 0.0692(14) Uani 1 1 d . . .
H17A H 0.4325 0.1984 0.3371 0.104 Uiso 1 1 calc R . .
H17B H 0.5979 0.1590 0.3218 0.104 Uiso 1 1 calc R . .
H17C H 0.4722 0.1404 0.2603 0.104 Uiso 1 1 calc R . .
C18 C 0.6201(6) 0.3675(4) 0.3255(3) 0.0765(15) Uani 1 1 d . . .
H18A H 0.5493 0.3782 0.3662 0.115 Uiso 1 1 calc R . .
H18B H 0.6483 0.4359 0.3045 0.115 Uiso 1 1 calc R . .
H18C H 0.7084 0.3319 0.3449 0.115 Uiso 1 1 calc R . .
C19 C 0.2439(5) 0.2224(3) 0.1645(2) 0.0484(10) Uani 1 1 d . . .
H19 H 0.3064 0.1609 0.1796 0.058 Uiso 1 1 calc R . .
C20 C 0.0827(5) 0.1029(3) 0.0996(3) 0.0702(14) Uani 1 1 d . . .
H20A H 0.1393 0.0475 0.1248 0.105 Uiso 1 1 calc R . .
H20B H 0.0573 0.0797 0.0489 0.105 Uiso 1 1 calc R . .
H20C H -0.0082 0.1171 0.1276 0.105 Uiso 1 1 calc R . .
C21 C -0.0880(5) 0.4627(4) 0.0388(3) 0.0781(16) Uani 1 1 d . . .
H21A H -0.0892 0.4784 -0.0147 0.117 Uiso 1 1 calc R . .
H21B H -0.1898 0.4595 0.0576 0.117 Uiso 1 1 calc R . .
H21C H -0.0393 0.3947 0.0472 0.117 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 C6 1.423(4) . ?
O1 H1 0.8200 . ?
O2 C19 1.428(5) . ?
O2 C7 1.454(4) . ?
O3 C19 1.402(4) . ?
O3 C20 1.426(4) . ?
O4 C14 1.441(4) . ?
O4 H4 0.8200 . ?
C1 C2 1.522(5) . ?
C1 C10 1.526(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.526(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.542(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C17 1.531(6) . ?
C4 C18 1.551(6) . ?
C4 C5 1.553(5) . ?
C5 C6 1.544(5) . ?
C5 C10 1.563(5) . ?
C5 H5 0.9800 . ?
C6 C7 1.525(5) . ?
C6 H6 0.9800 . ?
C7 C8 1.507(5) . ?
C7 H7 0.9800 . ?
C8 C9 1.323(5) . ?
C8 C14 1.502(5) . ?
C9 C11 1.504(5) . ?
C9 C10 1.524(5) . ?
C10 C19 1.547(5) . ?
C11 C12 1.528(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.535(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C15 1.526(6) . ?
C13 C21 1.534(6) . ?
C13 C14 1.551(5) . ?
C14 H14 0.9800 . ?
C15 C16 1.311(6) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9300 . ?
C16 H16B 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 H19 0.9800 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C6 O1 H1 109.5 . . ?
C19 O2 C7 113.1(3) . . ?
C19 O3 C20 112.8(3) . . ?
C14 O4 H4 109.5 . . ?
C2 C1 C10 113.5(4) . . ?
C2 C1 H1A 108.9 . . ?
C10 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
C10 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C1 C2 C3 110.4(4) . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C2 C3 C4 112.7(4) . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C17 C4 C3 109.6(4) . . ?
C17 C4 C18 107.0(4) . . ?
C3 C4 C18 107.5(4) . . ?
C17 C4 C5 115.7(4) . . ?
C3 C4 C5 108.9(3) . . ?
C18 C4 C5 107.8(3) . . ?
C6 C5 C4 115.0(3) . . ?
C6 C5 C10 110.1(3) . . ?
C4 C5 C10 116.6(3) . . ?
C6 C5 H5 104.5 . . ?
C4 C5 H5 104.5 . . ?
C10 C5 H5 104.5 . . ?
O1 C6 C7 111.6(4) . . ?
O1 C6 C5 114.2(3) . . ?
C7 C6 C5 107.8(3) . . ?
O1 C6 H6 107.7 . . ?
C7 C6 H6 107.7 . . ?
C5 C6 H6 107.7 . . ?
O2 C7 C8 110.7(3) . . ?
O2 C7 C6 105.8(3) . . ?
C8 C7 C6 107.9(3) . . ?
O2 C7 H7 110.8 . . ?
C8 C7 H7 110.8 . . ?
C6 C7 H7 110.8 . . ?
C9 C8 C14 124.0(4) . . ?
C9 C8 C7 113.9(4) . . ?
C14 C8 C7 121.8(4) . . ?
C8 C9 C11 123.2(4) . . ?
C8 C9 C10 113.8(3) . . ?
C11 C9 C10 123.0(3) . . ?
C9 C10 C1 114.2(3) . . ?
C9 C10 C19 104.0(3) . . ?
C1 C10 C19 112.4(3) . . ?
C9 C10 C5 105.1(3) . . ?
C1 C10 C5 111.3(3) . . ?
C19 C10 C5 109.4(3) . . ?
C9 C11 C12 112.4(3) . . ?
C9 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C9 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C13 112.6(3) . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C15 C13 C21 108.4(4) . . ?
C15 C13 C12 110.8(4) . . ?
C21 C13 C12 111.8(4) . . ?
C15 C13 C14 108.6(4) . . ?
C21 C13 C14 108.2(4) . . ?
C12 C13 C14 108.9(4) . . ?
O4 C14 C8 104.7(3) . . ?
O4 C14 C13 112.1(3) . . ?
C8 C14 C13 111.0(3) . . ?
O4 C14 H14 109.6 . . ?
C8 C14 H14 109.6 . . ?
C13 C14 H14 109.6 . . ?
C16 C15 C13 128.2(5) . . ?
C16 C15 H15 115.9 . . ?
C13 C15 H15 115.9 . . ?
C15 C16 H16A 120.0 . . ?
C15 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C4 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 . . ?
O3 C19 O2 111.6(3) . . ?
O3 C19 C10 108.0(3) . . ?
O2 C19 C10 110.0(3) . . ?
O3 C19 H19 109.1 . . ?
O2 C19 H19 109.1 . . ?
C10 C19 H19 109.1 . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C13 C21 H21A 109.5 . . ?
C13 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C13 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C10 C1 C2 C3 -56.8(5) . . . . ?
C1 C2 C3 C4 60.1(5) . . . . ?
C2 C3 C4 C17 73.2(5) . . . . ?
C2 C3 C4 C18 -170.8(4) . . . . ?
C2 C3 C4 C5 -54.3(5) . . . . ?
C17 C4 C5 C6 54.7(5) . . . . ?
C3 C4 C5 C6 178.6(3) . . . . ?
C18 C4 C5 C6 -65.0(4) . . . . ?
C17 C4 C5 C10 -76.6(5) . . . . ?
C3 C4 C5 C10 47.4(5) . . . . ?
C18 C4 C5 C10 163.8(4) . . . . ?
C4 C5 C6 O1 99.5(4) . . . . ?
C10 C5 C6 O1 -126.2(4) . . . . ?
C4 C5 C6 C7 -135.9(3) . . . . ?
C10 C5 C6 C7 -1.6(4) . . . . ?
C19 O2 C7 C8 45.6(5) . . . . ?
C19 O2 C7 C6 -71.1(4) . . . . ?
O1 C6 C7 O2 -171.6(3) . . . . ?
C5 C6 C7 O2 62.3(4) . . . . ?
O1 C6 C7 C8 69.9(4) . . . . ?
C5 C6 C7 C8 -56.3(4) . . . . ?
O2 C7 C8 C9 -54.3(5) . . . . ?
C6 C7 C8 C9 61.1(4) . . . . ?
O2 C7 C8 C14 131.5(4) . . . . ?
C6 C7 C8 C14 -113.1(4) . . . . ?
C14 C8 C9 C11 -7.0(6) . . . . ?
C7 C8 C9 C11 178.9(3) . . . . ?
C14 C8 C9 C10 174.0(3) . . . . ?
C7 C8 C9 C10 0.0(5) . . . . ?
C8 C9 C10 C1 179.1(3) . . . . ?
C11 C9 C10 C1 0.1(5) . . . . ?
C8 C9 C10 C19 56.2(4) . . . . ?
C11 C9 C10 C19 -122.7(4) . . . . ?
C8 C9 C10 C5 -58.7(4) . . . . ?
C11 C9 C10 C5 122.3(4) . . . . ?
C2 C1 C10 C9 167.4(3) . . . . ?
C2 C1 C10 C19 -74.5(4) . . . . ?
C2 C1 C10 C5 48.6(4) . . . . ?
C6 C5 C10 C9 57.3(4) . . . . ?
C4 C5 C10 C9 -169.2(3) . . . . ?
C6 C5 C10 C1 -178.6(3) . . . . ?
C4 C5 C10 C1 -45.1(4) . . . . ?
C6 C5 C10 C19 -53.8(4) . . . . ?
C4 C5 C10 C19 79.7(4) . . . . ?
C8 C9 C11 C12 14.9(6) . . . . ?
C10 C9 C11 C12 -166.2(3) . . . . ?
C9 C11 C12 C13 -41.6(5) . . . . ?
C11 C12 C13 C15 178.9(4) . . . . ?
C11 C12 C13 C21 -60.0(5) . . . . ?
C11 C12 C13 C14 59.5(5) . . . . ?
C9 C8 C14 O4 -96.6(5) . . . . ?
C7 C8 C14 O4 77.0(4) . . . . ?
C9 C8 C14 C13 24.6(6) . . . . ?
C7 C8 C14 C13 -161.8(4) . . . . ?
C15 C13 C14 O4 -53.0(5) . . . . ?
C21 C13 C14 O4 -170.5(3) . . . . ?
C12 C13 C14 O4 67.8(4) . . . . ?
C15 C13 C14 C8 -169.8(3) . . . . ?
C21 C13 C14 C8 72.8(5) . . . . ?
C12 C13 C14 C8 -49.0(5) . . . . ?
C21 C13 C15 C16 -125.0(6) . . . . ?
C12 C13 C15 C16 -2.0(8) . . . . ?
C14 C13 C15 C16 117.6(6) . . . . ?
C20 O3 C19 O2 -63.9(4) . . . . ?
C20 O3 C19 C10 175.1(3) . . . . ?
C7 O2 C19 O3 -107.8(4) . . . . ?
C7 O2 C19 C10 12.1(4) . . . . ?
C9 C10 C19 O3 59.6(4) . . . . ?
C1 C10 C19 O3 -64.4(4) . . . . ?
C5 C10 C19 O3 171.5(3) . . . . ?
C9 C10 C19 O2 -62.4(4) . . . . ?
C1 C10 C19 O2 173.6(3) . . . . ?
C5 C10 C19 O2 49.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        66.14
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_150522b
_database_code_depnum_ccdc_archive 'CCDC 1462859'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-12-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        sd310-40
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H32 O3'
_chemical_formula_weight         320.46

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   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                   6.6729(5)
_cell_length_b                   11.9119(9)
_cell_length_c                   23.5741(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1873.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    689
_cell_measurement_theta_min      4.0570
_cell_measurement_theta_max      60.9380

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8776
_exptl_absorpt_correction_T_max  0.9603
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5790
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_sigmaI/netI    0.1665
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.75
_diffrn_reflns_theta_max         66.20
_reflns_number_total             3169
_reflns_number_gt                1091
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0540P)²+1.8086P] 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     SHELXL
_refine_ls_extinction_coef       0.0010(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(14)
_refine_ls_number_reflns         3169
_refine_ls_number_parameters     218
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2224
_refine_ls_R_factor_gt           0.0960
_refine_ls_wR_factor_ref         0.2979
_refine_ls_wR_factor_gt          0.2657
_refine_ls_goodness_of_fit_ref   1.270
_refine_ls_restrained_S_all      1.270
_refine_ls_shift/su_max          0.001
_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 0.4103(11) 0.7760(6) 0.5798(3) 0.070(2) Uani 1 1 d . . .
H1 H 0.5033 0.8199 0.5748 0.084 Uiso 1 1 calc R . .
O2 O 0.2646(12) 0.4232(5) 0.9074(3) 0.074(2) Uani 1 1 d . . .
H2 H 0.1775 0.3962 0.9277 0.089 Uiso 1 1 calc R . .
O3 O 0.5307(13) 0.6601(7) 0.4755(3) 0.103(3) Uani 1 1 d . . .
H3C H 0.5067 0.6975 0.5055 0.123 Uiso 1 1 d R . .
H3D H 0.6424 0.6816 0.4620 0.123 Uiso 1 1 d R . .
C1 C 0.2313(19) 0.8129(8) 0.7305(4) 0.061(3) Uani 1 1 d . . .
H1A H 0.1321 0.8632 0.7466 0.073 Uiso 1 1 calc R . .
H1B H 0.3602 0.8320 0.7469 0.073 Uiso 1 1 calc R . .
C2 C 0.2405(19) 0.8312(8) 0.6665(4) 0.066(3) Uani 1 1 d . . .
H2A H 0.1091 0.8184 0.6501 0.079 Uiso 1 1 calc R . .
H2B H 0.2789 0.9082 0.6587 0.079 Uiso 1 1 calc R . .
C3 C 0.3902(18) 0.7522(9) 0.6401(4) 0.062(3) Uani 1 1 d . . .
H3 H 0.5205 0.7656 0.6580 0.074 Uiso 1 1 calc R . .
C4 C 0.3358(18) 0.6276(9) 0.6488(5) 0.060(3) Uani 1 1 d . . .
C5 C 0.3136(17) 0.6094(8) 0.7141(4) 0.055(3) Uani 1 1 d . . .
H5 H 0.4483 0.6218 0.7294 0.066 Uiso 1 1 calc R . .
C6 C 0.262(2) 0.4872(8) 0.7297(4) 0.066(3) Uani 1 1 d . . .
H6A H 0.1364 0.4663 0.7121 0.079 Uiso 1 1 calc R . .
H6B H 0.3658 0.4377 0.7152 0.079 Uiso 1 1 calc R . .
C7 C 0.2460(17) 0.4729(8) 0.7930(4) 0.060(3) Uani 1 1 d . . .
H7 H 0.2488 0.4001 0.8072 0.072 Uiso 1 1 calc R . .
C8 C 0.2282(18) 0.5551(9) 0.8295(4) 0.057(3) Uani 1 1 d . . .
C9 C 0.2116(16) 0.6733(9) 0.8100(4) 0.054(3) Uani 1 1 d . . .
C10 C 0.1780(17) 0.6915(9) 0.7470(4) 0.054(3) Uani 1 1 d . . .
C11 C 0.2195(17) 0.7553(9) 0.8480(4) 0.063(3) Uani 1 1 d . . .
H11 H 0.2054 0.8285 0.8348 0.075 Uiso 1 1 calc R . .
C12 C 0.2495(19) 0.7394(8) 0.9106(4) 0.067(3) Uani 1 1 d . . .
H12A H 0.1225 0.7511 0.9297 0.081 Uiso 1 1 calc R . .
H12B H 0.3422 0.7960 0.9242 0.081 Uiso 1 1 calc R . .
C13 C 0.331(2) 0.6226(10) 0.9267(4) 0.067(3) Uani 1 1 d . A .
C14 C 0.2104(17) 0.5359(8) 0.8923(4) 0.058(3) Uani 1 1 d . . .
H14 H 0.0689 0.5457 0.9023 0.069 Uiso 1 1 calc R . .
C15 C 0.552(2) 0.6118(11) 0.9116(6) 0.081(4) Uani 1 1 d D . .
H15 H 0.6140 0.5452 0.9222 0.097 Uiso 0.806(16) 1 calc PR A 1
H15' H 0.6069 0.6291 0.8765 0.097 Uiso 0.194(16) 1 d PR A 2
C16 C 0.666(3) 0.6868(15) 0.8849(7) 0.102(6) Uani 0.806(16) 1 d P A 1
H16A H 0.7912 0.7058 0.8997 0.122 Uiso 0.806(16) 1 calc PR A 1
H16B H 0.6217 0.7202 0.8516 0.122 Uiso 0.806(16) 1 calc PR A 1
C16' C 0.646(10) 0.575(6) 0.9585(18) 0.102(6) Uani 0.194(16) 1 d PD A 2
H16C H 0.7725 0.6027 0.9676 0.122 Uiso 0.194(16) 1 calc PR A 2
H16D H 0.5851 0.5222 0.9817 0.122 Uiso 0.194(16) 1 calc PR A 2
C17 C 0.1505(19) 0.5943(10) 0.6138(5) 0.079(4) Uani 1 1 d . . .
H17A H 0.1167 0.5174 0.6214 0.119 Uiso 1 1 calc R . .
H17B H 0.1795 0.6029 0.5741 0.119 Uiso 1 1 calc R . .
H17C H 0.0398 0.6417 0.6239 0.119 Uiso 1 1 calc R . .
C18 C 0.5137(18) 0.5551(10) 0.6274(5) 0.076(4) Uani 1 1 d . . .
H18A H 0.6304 0.5707 0.6499 0.114 Uiso 1 1 calc R . .
H18B H 0.5408 0.5728 0.5885 0.114 Uiso 1 1 calc R . .
H18C H 0.4800 0.4771 0.6307 0.114 Uiso 1 1 calc R . .
C19 C -0.0512(17) 0.6711(10) 0.7370(5) 0.076(4) Uani 1 1 d . . .
H19A H -0.0816 0.5933 0.7431 0.113 Uiso 1 1 calc R . .
H19B H -0.0851 0.6912 0.6988 0.113 Uiso 1 1 calc R . .
H19C H -0.1273 0.7163 0.7629 0.113 Uiso 1 1 calc R . .
C20 C 0.301(2) 0.6028(10) 0.9908(4) 0.097(5) Uani 1 1 d . . .
H20A H 0.3693 0.5351 1.0018 0.146 Uiso 1 1 calc R A .
H20B H 0.1611 0.5958 0.9990 0.146 Uiso 1 1 calc R . .
H20C H 0.3558 0.6651 1.0115 0.146 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 C3 1.456(11) . ?
O1 H1 0.8200 . ?
O2 C14 1.435(10) . ?
O2 H2 0.8200 . ?
O3 H3C 0.8501 . ?
O3 H3D 0.8501 . ?
C1 C2 1.525(11) . ?
C1 C10 1.539(12) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.508(13) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.541(14) . ?
C3 H3 0.9800 . ?
C4 C17 1.540(15) . ?
C4 C18 1.552(14) . ?
C4 C5 1.560(13) . ?
C5 C6 1.540(12) . ?
C5 C10 1.542(13) . ?
C5 H5 0.9800 . ?
C6 C7 1.504(13) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.310(12) . ?
C7 H7 0.9300 . ?
C8 C9 1.485(12) . ?
C8 C14 1.502(13) . ?
C9 C11 1.327(12) . ?
C9 C10 1.518(13) . ?
C10 C19 1.567(15) . ?
C11 C12 1.500(13) . ?
C11 H11 0.9300 . ?
C12 C13 1.541(14) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C15 1.523(17) . ?
C13 C14 1.540(14) . ?
C13 C20 1.541(13) . ?
C14 H14 0.9800 . ?
C15 C16 1.334(18) . ?
C15 C16' 1.344(10) . ?
C15 H15 0.9300 . ?
C15 H15' 0.9299 . ?
C16 H15' 0.8194 . ?
C16 H16A 0.9300 . ?
C16 H16B 0.9300 . ?
C16' H16C 0.9300 . ?
C16' H16D 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 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 109.5 . . ?
C14 O2 H2 109.5 . . ?
H3C O3 H3D 108.6 . . ?
C2 C1 C10 113.2(8) . . ?
C2 C1 H1A 108.9 . . ?
C10 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
C10 C1 H1B 108.9 . . ?
H1A C1 H1B 107.8 . . ?
C3 C2 C1 110.2(9) . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
O1 C3 C2 110.0(8) . . ?
O1 C3 C4 109.9(8) . . ?
C2 C3 C4 113.0(9) . . ?
O1 C3 H3 107.9 . . ?
C2 C3 H3 107.9 . . ?
C4 C3 H3 107.9 . . ?
C17 C4 C3 111.4(10) . . ?
C17 C4 C18 107.2(9) . . ?
C3 C4 C18 108.2(9) . . ?
C17 C4 C5 114.7(10) . . ?
C3 C4 C5 106.7(8) . . ?
C18 C4 C5 108.4(9) . . ?
C6 C5 C10 110.4(9) . . ?
C6 C5 C4 112.9(8) . . ?
C10 C5 C4 117.7(9) . . ?
C6 C5 H5 104.9 . . ?
C10 C5 H5 104.9 . . ?
C4 C5 H5 104.9 . . ?
C7 C6 C5 111.2(8) . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 125.0(9) . . ?
C8 C7 H7 117.5 . . ?
C6 C7 H7 117.5 . . ?
C7 C8 C9 120.8(9) . . ?
C7 C8 C14 122.8(10) . . ?
C9 C8 C14 116.3(9) . . ?
C11 C9 C8 119.1(9) . . ?
C11 C9 C10 124.2(10) . . ?
C8 C9 C10 116.7(9) . . ?
C9 C10 C1 110.3(8) . . ?
C9 C10 C5 108.4(9) . . ?
C1 C10 C5 109.4(9) . . ?
C9 C10 C19 105.6(9) . . ?
C1 C10 C19 109.5(10) . . ?
C5 C10 C19 113.5(9) . . ?
C9 C11 C12 125.2(10) . . ?
C9 C11 H11 117.4 . . ?
C12 C11 H11 117.4 . . ?
C11 C12 C13 113.8(9) . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C15 C13 C14 109.0(10) . . ?
C15 C13 C12 111.0(11) . . ?
C14 C13 C12 107.0(9) . . ?
C15 C13 C20 109.8(11) . . ?
C14 C13 C20 110.4(10) . . ?
C12 C13 C20 109.6(9) . . ?
O2 C14 C8 111.5(8) . . ?
O2 C14 C13 111.4(9) . . ?
C8 C14 C13 112.1(9) . . ?
O2 C14 H14 107.2 . . ?
C8 C14 H14 107.2 . . ?
C13 C14 H14 107.2 . . ?
C16 C15 C16' 110(3) . . ?
C16 C15 C13 127.5(14) . . ?
C16' C15 C13 107(3) . . ?
C16 C15 H15 116.2 . . ?
C16' C15 H15 45.0 . . ?
C13 C15 H15 116.2 . . ?
C16 C15 H15' 37.3 . . ?
C16' C15 H15' 128.2 . . ?
C13 C15 H15' 125.0 . . ?
H15 C15 H15' 104.6 . . ?
C15 C16 H15' 43.5 . . ?
C15 C16 H16A 120.0 . . ?
H15' C16 H16A 136.8 . . ?
C15 C16 H16B 120.0 . . ?
H15' C16 H16B 89.8 . . ?
H16A C16 H16B 120.0 . . ?
C15 C16' H16C 120.0 . . ?
C15 C16' H16D 120.0 . . ?
H16C C16' H16D 120.0 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C4 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 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 C20 H20A 109.5 . . ?
C13 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C13 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C10 C1 C2 C3 -57.3(13) . . . . ?
C1 C2 C3 O1 -175.5(9) . . . . ?
C1 C2 C3 C4 61.3(12) . . . . ?
O1 C3 C4 C17 -53.2(12) . . . . ?
C2 C3 C4 C17 70.1(11) . . . . ?
O1 C3 C4 C18 64.5(12) . . . . ?
C2 C3 C4 C18 -172.3(9) . . . . ?
O1 C3 C4 C5 -179.1(9) . . . . ?
C2 C3 C4 C5 -55.8(12) . . . . ?
C17 C4 C5 C6 57.0(14) . . . . ?
C3 C4 C5 C6 -179.0(10) . . . . ?
C18 C4 C5 C6 -62.7(13) . . . . ?
C17 C4 C5 C10 -73.3(12) . . . . ?
C3 C4 C5 C10 50.6(13) . . . . ?
C18 C4 C5 C10 166.9(9) . . . . ?
C10 C5 C6 C7 -47.1(13) . . . . ?
C4 C5 C6 C7 179.0(9) . . . . ?
C5 C6 C7 C8 15.6(18) . . . . ?
C6 C7 C8 C9 3(2) . . . . ?
C6 C7 C8 C14 179.4(10) . . . . ?
C7 C8 C9 C11 -171.5(12) . . . . ?
C14 C8 C9 C11 12.2(17) . . . . ?
C7 C8 C9 C10 10.9(17) . . . . ?
C14 C8 C9 C10 -165.4(10) . . . . ?
C11 C9 C10 C1 20.7(16) . . . . ?
C8 C9 C10 C1 -161.8(10) . . . . ?
C11 C9 C10 C5 140.6(11) . . . . ?
C8 C9 C10 C5 -41.9(13) . . . . ?
C11 C9 C10 C19 -97.5(13) . . . . ?
C8 C9 C10 C19 80.1(12) . . . . ?
C2 C1 C10 C9 168.8(10) . . . . ?
C2 C1 C10 C5 49.6(13) . . . . ?
C2 C1 C10 C19 -75.4(12) . . . . ?
C6 C5 C10 C9 59.8(12) . . . . ?
C4 C5 C10 C9 -168.6(9) . . . . ?
C6 C5 C10 C1 -179.8(9) . . . . ?
C4 C5 C10 C1 -48.3(13) . . . . ?
C6 C5 C10 C19 -57.2(12) . . . . ?
C4 C5 C10 C19 74.3(12) . . . . ?
C8 C9 C11 C12 1.6(19) . . . . ?
C10 C9 C11 C12 179.0(10) . . . . ?
C9 C11 C12 C13 16.6(18) . . . . ?
C11 C12 C13 C15 74.0(13) . . . . ?
C11 C12 C13 C14 -44.8(13) . . . . ?
C11 C12 C13 C20 -164.5(11) . . . . ?
C7 C8 C14 O2 14.4(17) . . . . ?
C9 C8 C14 O2 -169.4(10) . . . . ?
C7 C8 C14 C13 140.1(12) . . . . ?
C9 C8 C14 C13 -43.7(14) . . . . ?
C15 C13 C14 O2 64.1(12) . . . . ?
C12 C13 C14 O2 -175.7(9) . . . . ?
C20 C13 C14 O2 -56.5(13) . . . . ?
C15 C13 C14 C8 -61.6(13) . . . . ?
C12 C13 C14 C8 58.5(12) . . . . ?
C20 C13 C14 C8 177.7(10) . . . . ?
C14 C13 C15 C16 113.7(16) . . . . ?
C12 C13 C15 C16 -3.9(19) . . . . ?
C20 C13 C15 C16 -125.3(16) . . . . ?
C14 C13 C15 C16' -114(3) . . . . ?
C12 C13 C15 C16' 129(3) . . . . ?
C20 C13 C15 C16' 7(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        66.20
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_150503c
_database_code_depnum_ccdc_archive 'CCDC 1462860'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-12-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        sd310-20
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H32 O4'
_chemical_formula_weight         360.48

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   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                   9.4327(6)
_cell_length_b                   13.1356(9)
_cell_length_c                   16.7370(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2073.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1180
_cell_measurement_theta_min      5.3820
_cell_measurement_theta_max      64.1990

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.7678
_exptl_absorpt_correction_T_max  0.8860
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4556
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.28
_diffrn_reflns_theta_max         66.17
_reflns_number_total             2922
_reflns_number_gt                2104
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0450P)²+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.0026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_number_reflns         2922
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_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 0.2211(3) 0.2339(3) 0.59841(14) 0.1001(11) Uani 1 1 d . . .
H1 H 0.1462 0.2487 0.6204 0.150 Uiso 1 1 calc R . .
O2 O 0.9711(2) 0.2663(2) 0.68568(14) 0.0881(9) Uani 1 1 d . . .
O3 O 0.9175(2) 0.30253(17) 0.87863(13) 0.0628(6) Uani 1 1 d . . .
O4 O 1.1452(3) 0.3480(3) 0.8607(2) 0.1111(12) Uani 1 1 d . . .
C1 C 0.4343(3) 0.1354(3) 0.77377(18) 0.0657(10) Uani 1 1 d . . .
H1A H 0.4206 0.0759 0.8072 0.079 Uiso 1 1 calc R . .
H1B H 0.4277 0.1952 0.8076 0.079 Uiso 1 1 calc R . .
C2 C 0.3177(4) 0.1393(4) 0.7113(2) 0.0775(12) Uani 1 1 d . . .
H2A H 0.3206 0.0775 0.6796 0.093 Uiso 1 1 calc R . .
H2B H 0.2264 0.1421 0.7379 0.093 Uiso 1 1 calc R . .
C3 C 0.3327(3) 0.2304(3) 0.65682(19) 0.0705(11) Uani 1 1 d . . .
H3 H 0.3268 0.2921 0.6896 0.085 Uiso 1 1 calc R . .
C4 C 0.4743(3) 0.2317(3) 0.61239(17) 0.0555(8) Uani 1 1 d . . .
C5 C 0.5929(3) 0.2200(2) 0.67559(16) 0.0474(7) Uani 1 1 d . . .
H5 H 0.5852 0.2814 0.7086 0.057 Uiso 1 1 calc R . .
C6 C 0.7414(3) 0.2256(3) 0.63967(17) 0.0621(10) Uani 1 1 d . . .
H6A H 0.7569 0.1660 0.6066 0.075 Uiso 1 1 calc R . .
H6B H 0.7474 0.2851 0.6055 0.075 Uiso 1 1 calc R . .
C7 C 0.8552(3) 0.2312(3) 0.7012(2) 0.0585(9) Uani 1 1 d . . .
C8 C 0.8237(3) 0.1921(2) 0.78189(17) 0.0491(8) Uani 1 1 d . . .
C9 C 0.6998(3) 0.1452(2) 0.79809(18) 0.0499(8) Uani 1 1 d . . .
C10 C 0.5834(3) 0.1310(3) 0.73569(17) 0.0522(8) Uani 1 1 d . . .
C11 C 0.6798(4) 0.0941(3) 0.87801(18) 0.0679(10) Uani 1 1 d . . .
H11A H 0.6741 0.0212 0.8692 0.081 Uiso 1 1 calc R . .
H11B H 0.5895 0.1158 0.8998 0.081 Uiso 1 1 calc R . .
C12 C 0.7939(4) 0.1139(3) 0.94041(19) 0.0616(9) Uani 1 1 d . . .
H12A H 0.7908 0.0601 0.9801 0.074 Uiso 1 1 calc R . .
H12B H 0.7732 0.1776 0.9673 0.074 Uiso 1 1 calc R . .
C13 C 0.9429(4) 0.1192(3) 0.90529(19) 0.0561(8) Uani 1 1 d . . .
C14 C 1.0524(4) 0.1441(3) 0.9685(2) 0.0711(10) Uani 1 1 d . . .
H14 H 1.1454 0.1502 0.9506 0.085 Uiso 1 1 calc R . .
C15 C 1.0327(5) 0.1581(3) 1.0445(2) 0.0881(13) Uani 1 1 d . . .
H15A H 0.9421 0.1530 1.0660 0.106 Uiso 1 1 calc R . .
H15B H 1.1093 0.1731 1.0775 0.106 Uiso 1 1 calc R . .
C16 C 0.9413(3) 0.2035(2) 0.84178(18) 0.0521(8) Uani 1 1 d . . .
H16 H 1.0325 0.2042 0.8137 0.062 Uiso 1 1 calc R . .
C17 C 0.4781(4) 0.1502(3) 0.54589(18) 0.0711(11) Uani 1 1 d . . .
H17A H 0.4183 0.1711 0.5025 0.107 Uiso 1 1 calc R . .
H17B H 0.4449 0.0865 0.5668 0.107 Uiso 1 1 calc R . .
H17C H 0.5736 0.1424 0.5270 0.107 Uiso 1 1 calc R . .
C18 C 0.4898(4) 0.3349(3) 0.5709(2) 0.0758(12) Uani 1 1 d . . .
H18A H 0.5080 0.3866 0.6101 0.114 Uiso 1 1 calc R . .
H18B H 0.4038 0.3507 0.5428 0.114 Uiso 1 1 calc R . .
H18C H 0.5672 0.3321 0.5337 0.114 Uiso 1 1 calc R . .
C19 C 0.6079(4) 0.0247(3) 0.6989(2) 0.0715(11) Uani 1 1 d . . .
H19A H 0.6153 -0.0249 0.7409 0.107 Uiso 1 1 calc R . .
H19B H 0.6939 0.0252 0.6683 0.107 Uiso 1 1 calc R . .
H19C H 0.5296 0.0076 0.6648 0.107 Uiso 1 1 calc R . .
C20 C 0.9848(4) 0.0198(3) 0.8646(2) 0.0757(11) Uani 1 1 d . . .
H20A H 0.9806 -0.0348 0.9027 0.114 Uiso 1 1 calc R . .
H20B H 1.0795 0.0255 0.8442 0.114 Uiso 1 1 calc R . .
H20C H 0.9206 0.0061 0.8214 0.114 Uiso 1 1 calc R . .
C21 C 1.0279(5) 0.3682(3) 0.8818(3) 0.0784(12) Uani 1 1 d . . .
C22 C 0.9812(5) 0.4675(3) 0.9165(3) 0.118(2) Uani 1 1 d . . .
H22A H 0.9421 0.5095 0.8750 0.177 Uiso 1 1 calc R . .
H22B H 1.0611 0.5014 0.9401 0.177 Uiso 1 1 calc R . .
H22C H 0.9105 0.4555 0.9566 0.177 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 C3 1.437(4) . ?
O1 H1 0.8200 . ?
O2 C7 1.215(4) . ?
O3 C21 1.354(4) . ?
O3 C16 1.457(4) . ?
O4 C21 1.191(5) . ?
C1 C2 1.518(5) . ?
C1 C10 1.545(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.512(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.529(4) . ?
C3 H3 0.9800 . ?
C4 C18 1.530(5) . ?
C4 C17 1.544(4) . ?
C4 C5 1.547(4) . ?
C5 C6 1.526(4) . ?
C5 C10 1.545(4) . ?
C5 H5 0.9800 . ?
C6 C7 1.489(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.476(4) . ?
C8 C9 1.349(4) . ?
C8 C16 1.503(4) . ?
C9 C11 1.508(4) . ?
C9 C10 1.527(4) . ?
C10 C19 1.543(4) . ?
C11 C12 1.522(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.525(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.514(5) . ?
C13 C20 1.524(5) . ?
C13 C16 1.535(4) . ?
C14 C15 1.299(5) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9300 . ?
C15 H15B 0.9300 . ?
C16 H16 0.9800 . ?
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 1.494(6) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C3 O1 H1 109.5 . . ?
C21 O3 C16 117.8(3) . . ?
C2 C1 C10 112.1(3) . . ?
C2 C1 H1A 109.2 . . ?
C10 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
C10 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C3 C2 C1 112.0(3) . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
O1 C3 C2 111.6(3) . . ?
O1 C3 C4 108.0(3) . . ?
C2 C3 C4 112.5(3) . . ?
O1 C3 H3 108.2 . . ?
C2 C3 H3 108.2 . . ?
C4 C3 H3 108.2 . . ?
C3 C4 C18 108.3(3) . . ?
C3 C4 C17 111.3(3) . . ?
C18 C4 C17 106.5(2) . . ?
C3 C4 C5 107.3(2) . . ?
C18 C4 C5 109.2(3) . . ?
C17 C4 C5 114.0(3) . . ?
C6 C5 C10 110.2(2) . . ?
C6 C5 C4 112.9(2) . . ?
C10 C5 C4 118.6(3) . . ?
C6 C5 H5 104.5 . . ?
C10 C5 H5 104.5 . . ?
C4 C5 H5 104.5 . . ?
C7 C6 C5 113.1(2) . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
O2 C7 C8 120.6(3) . . ?
O2 C7 C6 121.4(3) . . ?
C8 C7 C6 118.0(3) . . ?
C9 C8 C7 121.2(3) . . ?
C9 C8 C16 123.4(3) . . ?
C7 C8 C16 115.3(3) . . ?
C8 C9 C11 119.3(3) . . ?
C8 C9 C10 122.8(3) . . ?
C11 C9 C10 117.5(3) . . ?
C9 C10 C19 106.0(3) . . ?
C9 C10 C1 111.6(2) . . ?
C19 C10 C1 109.5(3) . . ?
C9 C10 C5 108.1(3) . . ?
C19 C10 C5 114.6(3) . . ?
C1 C10 C5 107.0(3) . . ?
C9 C11 C12 116.4(3) . . ?
C9 C11 H11A 108.2 . . ?
C12 C11 H11A 108.2 . . ?
C9 C11 H11B 108.2 . . ?
C12 C11 H11B 108.2 . . ?
H11A C11 H11B 107.3 . . ?
C11 C12 C13 113.3(3) . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C20 108.7(3) . . ?
C14 C13 C12 111.7(3) . . ?
C20 C13 C12 111.8(3) . . ?
C14 C13 C16 109.5(3) . . ?
C20 C13 C16 108.1(3) . . ?
C12 C13 C16 106.9(3) . . ?
C15 C14 C13 128.1(4) . . ?
C15 C14 H14 116.0 . . ?
C13 C14 H14 116.0 . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
O3 C16 C8 104.9(3) . . ?
O3 C16 C13 110.6(2) . . ?
C8 C16 C13 113.4(3) . . ?
O3 C16 H16 109.3 . . ?
C8 C16 H16 109.3 . . ?
C13 C16 H16 109.3 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C4 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 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 C20 H20A 109.5 . . ?
C13 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C13 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C21 O3 124.1(4) . . ?
O4 C21 C22 125.7(4) . . ?
O3 C21 C22 110.2(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 . . ?

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 -58.8(5) . . . . ?
C1 C2 C3 O1 -179.5(3) . . . . ?
C1 C2 C3 C4 59.0(4) . . . . ?
O1 C3 C4 C18 66.2(4) . . . . ?
C2 C3 C4 C18 -170.2(3) . . . . ?
O1 C3 C4 C17 -50.5(4) . . . . ?
C2 C3 C4 C17 73.0(3) . . . . ?
O1 C3 C4 C5 -176.0(3) . . . . ?
C2 C3 C4 C5 -52.4(4) . . . . ?
C3 C4 C5 C6 -177.0(3) . . . . ?
C18 C4 C5 C6 -59.8(3) . . . . ?
C17 C4 C5 C6 59.2(4) . . . . ?
C3 C4 C5 C10 51.8(4) . . . . ?
C18 C4 C5 C10 169.0(3) . . . . ?
C17 C4 C5 C10 -71.9(3) . . . . ?
C10 C5 C6 C7 -54.1(4) . . . . ?
C4 C5 C6 C7 170.7(3) . . . . ?
C5 C6 C7 O2 -157.3(4) . . . . ?
C5 C6 C7 C8 23.1(5) . . . . ?
O2 C7 C8 C9 -174.3(4) . . . . ?
C6 C7 C8 C9 5.3(5) . . . . ?
O2 C7 C8 C16 2.5(5) . . . . ?
C6 C7 C8 C16 -177.9(3) . . . . ?
C7 C8 C9 C11 171.8(3) . . . . ?
C16 C8 C9 C11 -4.8(5) . . . . ?
C7 C8 C9 C10 -1.2(5) . . . . ?
C16 C8 C9 C10 -177.8(3) . . . . ?
C8 C9 C10 C19 93.9(4) . . . . ?
C11 C9 C10 C19 -79.3(4) . . . . ?
C8 C9 C10 C1 -147.0(3) . . . . ?
C11 C9 C10 C1 39.9(4) . . . . ?
C8 C9 C10 C5 -29.5(4) . . . . ?
C11 C9 C10 C5 157.3(3) . . . . ?
C2 C1 C10 C9 170.4(3) . . . . ?
C2 C1 C10 C19 -72.6(4) . . . . ?
C2 C1 C10 C5 52.3(4) . . . . ?
C6 C5 C10 C9 55.6(3) . . . . ?
C4 C5 C10 C9 -172.1(3) . . . . ?
C6 C5 C10 C19 -62.4(4) . . . . ?
C4 C5 C10 C19 69.9(4) . . . . ?
C6 C5 C10 C1 175.9(3) . . . . ?
C4 C5 C10 C1 -51.8(3) . . . . ?
C8 C9 C11 C12 9.6(5) . . . . ?
C10 C9 C11 C12 -177.0(3) . . . . ?
C9 C11 C12 C13 -37.6(5) . . . . ?
C11 C12 C13 C14 177.2(3) . . . . ?
C11 C12 C13 C20 -60.8(4) . . . . ?
C11 C12 C13 C16 57.4(4) . . . . ?
C20 C13 C14 C15 -122.2(5) . . . . ?
C12 C13 C14 C15 1.6(6) . . . . ?
C16 C13 C14 C15 119.8(5) . . . . ?
C21 O3 C16 C8 -129.0(3) . . . . ?
C21 O3 C16 C13 108.4(3) . . . . ?
C9 C8 C16 O3 -93.4(4) . . . . ?
C7 C8 C16 O3 89.9(3) . . . . ?
C9 C8 C16 C13 27.5(5) . . . . ?
C7 C8 C16 C13 -149.3(3) . . . . ?
C14 C13 C16 O3 -55.4(4) . . . . ?
C20 C13 C16 O3 -173.6(3) . . . . ?
C12 C13 C16 O3 65.8(3) . . . . ?
C14 C13 C16 C8 -172.9(3) . . . . ?
C20 C13 C16 C8 68.8(4) . . . . ?
C12 C13 C16 C8 -51.8(3) . . . . ?
C16 O3 C21 O4 -4.7(6) . . . . ?
C16 O3 C21 C22 176.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        66.17
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.031
