# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_SF9_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1555949'
_audit_update_record             
;
2017-06-14 deposited with the CCDC.
2017-08-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_STRVA01_SF9_0m_a            
;
PROBLEM: Flack parameter is too small
RESPONSE: The absolute configuration for this light atom structure
          cannot be determined reliably. However electronic and 
          vibrational circular dichroism (ECD, VCD) in solution, and 
          in the case of ECD also in the solid state confirmed the 
          chiral nature and overall configuration which are consistent 
          with the structure presented here. 
;
# end Validation Reply Form 
_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H34 O2'
_chemical_formula_sum            'C20 H34 O2'
_chemical_formula_weight         306.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.2203(8)
_cell_length_b                   16.092(2)
_cell_length_c                   9.4123(14)
_cell_angle_alpha                90
_cell_angle_beta                 102.898(4)
_cell_angle_gamma                90
_cell_volume                     918.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6244
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      26.25

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.108
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6844
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15753
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.360
_diffrn_reflns_theta_max         26.543
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             3772
_reflns_number_gt                3116
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.921
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.984

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0880P)²+0.2261P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 x determined using 1289 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.3(4)
_chemical_absolute_configuration '1S, 4R, 5R'
_refine_ls_number_reflns         3772
_refine_ls_number_parameters     204
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1380
_refine_ls_wR_factor_gt          0.1259
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_restrained_S_all      0.950
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6419(4) 0.54581(14) 0.5591(2) 0.0361(5) Uani 1 1 d . . . . .
O2 O 0.7379(3) 0.46286(12) 0.8252(2) 0.0291(5) Uani 1 1 d . . . . .
C1 C 0.5741(5) 0.41811(18) 0.8825(3) 0.0265(6) Uani 1 1 d . . . . .
C2 C 0.4148(6) 0.4846(2) 0.9145(4) 0.0344(7) Uani 1 1 d . . . . .
H2A H 0.2631 0.4663 0.8829 0.041 Uiso 1 1 calc R U . . .
H2B H 0.4444 0.4971 1.0178 0.041 Uiso 1 1 calc R U . . .
C3 C 0.4584(5) 0.55993(19) 0.8277(4) 0.0326(7) Uani 1 1 d . . . . .
H3A H 0.4309 0.6111 0.8751 0.039 Uiso 1 1 calc R U . . .
H3B H 0.3666 0.5589 0.7297 0.039 Uiso 1 1 calc R U . . .
C4 C 0.7016(5) 0.55165(18) 0.8251(3) 0.0296(7) Uani 1 1 d . . . . .
C5 C 0.7661(5) 0.5847(2) 0.6874(4) 0.0336(7) Uani 1 1 d . . . . .
H5 H 0.9224 0.5724 0.6948 0.040 Uiso 1 1 calc R U . . .
C6 C 0.7308(7) 0.6789(2) 0.6600(5) 0.0494(10) Uani 1 1 d . . . . .
H6A H 0.7215 0.7077 0.7490 0.059 Uiso 1 1 calc R U . . .
H6B H 0.8496 0.7028 0.6220 0.059 Uiso 1 1 calc R U . . .
C7 C 0.5141(7) 0.6836(2) 0.5487(4) 0.0477(9) Uani 1 1 d . . . . .
H7A H 0.5095 0.7323 0.4873 0.057 Uiso 1 1 calc R U . . .
H7B H 0.3908 0.6857 0.5960 0.057 Uiso 1 1 calc R U . . .
C8 C 0.5078(6) 0.6038(2) 0.4592(4) 0.0407(8) Uani 1 1 d . . . . .
C9 C 0.2766(6) 0.5676(2) 0.4130(4) 0.0456(9) Uani 1 1 d . . . . .
H9A H 0.1861 0.6065 0.3468 0.055 Uiso 1 1 calc R U . . .
H9B H 0.2150 0.5634 0.4987 0.055 Uiso 1 1 calc R U . . .
C10 C 0.2586(7) 0.4824(3) 0.3391(4) 0.0512(10) Uani 1 1 d . . . . .
H10A H 0.2135 0.4900 0.2344 0.061 Uiso 1 1 calc R U . . .
H10B H 0.4029 0.4564 0.3599 0.061 Uiso 1 1 calc R U . . .
C11 C 0.0955(7) 0.4247(3) 0.3883(5) 0.0579(11) Uani 1 1 d . . . . .
H11A H -0.0404 0.4553 0.3828 0.069 Uiso 1 1 calc R U . . .
H11B H 0.0626 0.3795 0.3185 0.069 Uiso 1 1 calc R U . . .
C12 C 0.1611(5) 0.3871(2) 0.5379(4) 0.0351(7) Uani 1 1 d . . . . .
C13 C 0.3652(6) 0.3924(2) 0.6201(4) 0.0404(8) Uani 1 1 d . . . . .
H13 H 0.4633 0.4236 0.5806 0.048 Uiso 1 1 calc R U . . .
C14 C 0.4588(6) 0.3556(2) 0.7656(4) 0.0357(8) Uani 1 1 d . . . . .
H14A H 0.5644 0.3131 0.7546 0.043 Uiso 1 1 calc R U . . .
H14B H 0.3408 0.3286 0.8003 0.043 Uiso 1 1 calc R U . . .
C15 C 0.6173(8) 0.6161(3) 0.3304(5) 0.0596(11) Uani 1 1 d . . . . .
H15A H 0.7568 0.6434 0.3634 0.089 Uiso 1 1 calc R U . . .
H15B H 0.5239 0.6497 0.2576 0.089 Uiso 1 1 calc R U . . .
H15C H 0.6400 0.5631 0.2894 0.089 Uiso 1 1 calc R U . . .
C16 C 0.8529(6) 0.5893(2) 0.9609(4) 0.0454(9) Uani 1 1 d . . . . .
H16A H 0.8198 0.5649 1.0467 0.068 Uiso 1 1 calc R U . . .
H16B H 0.8296 0.6482 0.9620 0.068 Uiso 1 1 calc R U . . .
H16C H 1.0039 0.5783 0.9592 0.068 Uiso 1 1 calc R U . . .
C17 C 0.6953(6) 0.3728(2) 1.0222(4) 0.0373(8) Uani 1 1 d . . . . .
H17 H 0.7651 0.4159 1.0907 0.045 Uiso 1 1 calc R U . . .
C18 C 0.5390(8) 0.3250(3) 1.0972(5) 0.0574(11) Uani 1 1 d . . . . .
H18A H 0.4798 0.2780 1.0387 0.086 Uiso 1 1 calc R U . . .
H18B H 0.4207 0.3608 1.1088 0.086 Uiso 1 1 calc R U . . .
H18C H 0.6184 0.3063 1.1911 0.086 Uiso 1 1 calc R U . . .
C19 C 0.8793(7) 0.3167(3) 0.9965(5) 0.0583(11) Uani 1 1 d . . . . .
H19A H 0.9750 0.3028 1.0884 0.087 Uiso 1 1 calc R U . . .
H19B H 0.9621 0.3451 0.9366 0.087 Uiso 1 1 calc R U . . .
H19C H 0.8170 0.2668 0.9484 0.087 Uiso 1 1 calc R U . . .
C20 C -0.0234(7) 0.3413(3) 0.5839(6) 0.0659(13) Uani 1 1 d . . . . .
H20A H 0.0371 0.3041 0.6624 0.099 Uiso 1 1 calc R U . . .
H20B H -0.1059 0.3102 0.5029 0.099 Uiso 1 1 calc R U . . .
H20C H -0.1189 0.3806 0.6159 0.099 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.426(4) . ?
O1 C8 1.449(4) . ?
O2 C4 1.446(4) . ?
O2 C1 1.447(4) . ?
C1 C2 1.532(4) . ?
C1 C14 1.544(4) . ?
C1 C17 1.545(4) . ?
C2 C3 1.520(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.525(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C16 1.533(4) . ?
C4 C5 1.534(4) . ?
C5 C6 1.545(5) . ?
C5 H5 0.9800 . ?
C6 C7 1.513(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.532(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.522(5) . ?
C8 C15 1.530(6) . ?
C9 C10 1.530(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.522(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.503(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.334(5) . ?
C12 C20 1.506(6) . ?
C13 C14 1.486(5) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C19 1.519(6) . ?
C17 C18 1.530(5) . ?
C17 H17 0.9800 . ?
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
C5 O1 C8 113.1(2) . . ?
C4 O2 C1 111.7(2) . . ?
O2 C1 C2 105.4(2) . . ?
O2 C1 C14 108.2(2) . . ?
C2 C1 C14 112.1(3) . . ?
O2 C1 C17 107.6(2) . . ?
C2 C1 C17 112.1(3) . . ?
C14 C1 C17 111.1(3) . . ?
C3 C2 C1 104.5(2) . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C2 C3 C4 103.6(3) . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
C4 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
O2 C4 C3 104.0(2) . . ?
O2 C4 C16 108.8(3) . . ?
C3 C4 C16 112.3(3) . . ?
O2 C4 C5 105.9(2) . . ?
C3 C4 C5 115.5(3) . . ?
C16 C4 C5 109.9(3) . . ?
O1 C5 C4 111.6(2) . . ?
O1 C5 C6 105.0(3) . . ?
C4 C5 C6 115.3(3) . . ?
O1 C5 H5 108.2 . . ?
C4 C5 H5 108.2 . . ?
C6 C5 H5 108.2 . . ?
C7 C6 C5 103.7(3) . . ?
C7 C6 H6A 111.0 . . ?
C5 C6 H6A 111.0 . . ?
C7 C6 H6B 111.0 . . ?
C5 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
C6 C7 C8 104.4(3) . . ?
C6 C7 H7A 110.9 . . ?
C8 C7 H7A 110.9 . . ?
C6 C7 H7B 110.9 . . ?
C8 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
O1 C8 C9 108.0(3) . . ?
O1 C8 C15 107.7(3) . . ?
C9 C8 C15 112.5(3) . . ?
O1 C8 C7 104.0(3) . . ?
C9 C8 C7 112.6(3) . . ?
C15 C8 C7 111.4(3) . . ?
C8 C9 C10 116.2(3) . . ?
C8 C9 H9A 108.2 . . ?
C10 C9 H9A 108.2 . . ?
C8 C9 H9B 108.2 . . ?
C10 C9 H9B 108.2 . . ?
H9A C9 H9B 107.4 . . ?
C11 C10 C9 113.2(3) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C10 118.1(3) . . ?
C12 C11 H11A 107.8 . . ?
C10 C11 H11A 107.8 . . ?
C12 C11 H11B 107.8 . . ?
C10 C11 H11B 107.8 . . ?
H11A C11 H11B 107.1 . . ?
C13 C12 C11 122.8(3) . . ?
C13 C12 C20 123.5(4) . . ?
C11 C12 C20 113.7(3) . . ?
C12 C13 C14 129.5(4) . . ?
C12 C13 H13 115.3 . . ?
C14 C13 H13 115.3 . . ?
C13 C14 C1 115.0(3) . . ?
C13 C14 H14A 108.5 . . ?
C1 C14 H14A 108.5 . . ?
C13 C14 H14B 108.5 . . ?
C1 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C16 H16A 109.5 . . ?
C4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C19 C17 C18 110.7(3) . . ?
C19 C17 C1 112.8(3) . . ?
C18 C17 C1 113.0(3) . . ?
C19 C17 H17 106.6 . . ?
C18 C17 H17 106.6 . . ?
C1 C17 H17 106.6 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 C20 H20A 109.5 . . ?
C12 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C12 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         0.318
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.057

_shelxl_version_number           2013-3

