# 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_cu_2014008.CIF
_database_code_depnum_ccdc_archive 'CCDC 1040484'
_audit_update_record             
;
2014-12-22 deposited with the CCDC.
2015-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        sinuflexolide
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H32 O5'
_chemical_formula_weight         352.46

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           monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   10.2341(15)
_cell_length_b                   10.4857(16)
_cell_length_c                   10.2341(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.97
_cell_angle_gamma                90.00
_cell_volume                     978.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6169
_cell_measurement_theta_min      4.50
_cell_measurement_theta_max      54.87

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7720
_exptl_absorpt_correction_T_max  0.8756
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_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            6490
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.85
_diffrn_reflns_theta_max         67.50
_reflns_number_total             2978
_reflns_number_gt                2894
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_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)+(0.1101P)²+0.0256P] 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       0.018(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   -0.1(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2978
_refine_ls_number_parameters     239
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1416
_refine_ls_wR_factor_gt          0.1362
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 0.28757(17) 0.99270(17) 0.41023(19) 0.0398(4) Uani 1 1 d . . .
H6 H 0.344(4) 1.062(4) 0.444(4) 0.060 Uiso 1 1 d . . .
O2 O 0.53759(18) 0.72280(14) 0.46233(17) 0.0376(4) Uani 1 1 d . . .
H7 H 0.602(4) 0.743(4) 0.445(4) 0.056 Uiso 1 1 d . . .
O3 O 0.0168(2) 0.5427(2) 0.7168(2) 0.0568(5) Uani 1 1 d . . .
H17 H -0.069(5) 0.558(4) 0.692(5) 0.085 Uiso 1 1 d . . .
O4 O -0.08978(17) 0.7611(2) 0.53141(17) 0.0474(5) Uani 1 1 d . . .
O5 O -0.28571(17) 0.7841(2) 0.32544(19) 0.0552(6) Uani 1 1 d . . .
C19 C 0.4373(4) 0.9979(3) 0.8105(4) 0.0596(7) Uani 1 1 d . . .
H13 H 0.3478 1.0062 0.7213 0.089 Uiso 1 1 calc R . .
H12 H 0.5060 1.0614 0.8130 0.089 Uiso 1 1 calc R . .
H1 H 0.4175 1.0093 0.8929 0.089 Uiso 1 1 calc R . .
C8 C 0.5010(2) 0.8674(2) 0.8172(2) 0.0351(5) Uani 1 1 d . . .
C9 C 0.6247(2) 0.8591(2) 0.7752(2) 0.0379(5) Uani 1 1 d . . .
H11 H 0.6549 0.7707 0.7811 0.046 Uiso 1 1 calc R . .
H10 H 0.7077 0.9071 0.8459 0.046 Uiso 1 1 calc R . .
C10 C 0.5852(2) 0.9097(2) 0.6202(2) 0.0347(5) Uani 1 1 d . . .
H26 H 0.5482 0.9961 0.6111 0.042 Uiso 1 1 calc R . .
H9 H 0.6730 0.9123 0.6067 0.042 Uiso 1 1 calc R . .
C11 C 0.4705(2) 0.8270(2) 0.5012(2) 0.0301(5) Uani 1 1 d . . .
H8 H 0.4120 0.7885 0.5446 0.036 Uiso 1 1 calc R . .
C12 C 0.3613(2) 0.8991(2) 0.3630(2) 0.0315(5) Uani 1 1 d . . .
C13 C 0.2443(2) 0.8088(2) 0.2533(2) 0.0356(5) Uani 1 1 d . . .
H5 H 0.1620 0.8604 0.1876 0.043 Uiso 1 1 calc R . .
H4 H 0.2853 0.7690 0.1945 0.043 Uiso 1 1 calc R . .
C14 C 0.1845(2) 0.7028(2) 0.3142(2) 0.0344(5) Uani 1 1 d . . .
H3 H 0.2663 0.6512 0.3809 0.041 Uiso 1 1 calc R . .
H30 H 0.1214 0.6484 0.2335 0.041 Uiso 1 1 calc R . .
C1 C 0.0977(2) 0.7477(2) 0.3956(2) 0.0318(5) Uani 1 1 d . . .
H31 H 0.1291 0.8352 0.4283 0.038 Uiso 1 1 calc R . .
C15 C -0.0666(2) 0.7512(2) 0.3046(2) 0.0375(5) Uani 1 1 d . . .
C17 C -0.1394(3) 0.7421(5) 0.1621(3) 0.0680(10) Uani 1 1 d . . .
H2 H -0.2412 0.7457 0.1163 0.082 Uiso 1 1 calc R . .
H32 H -0.0893 0.7320 0.1063 0.082 Uiso 1 1 calc R . .
C7 C 0.4555(2) 0.7640(2) 0.8611(2) 0.0356(5) Uani 1 1 d . . .
H25 H 0.4978 0.6871 0.8553 0.043 Uiso 1 1 calc R . .
C6 C 0.3442(3) 0.7567(3) 0.9187(2) 0.0432(6) Uani 1 1 d . . .
H24 H 0.2854 0.8337 0.8904 0.052 Uiso 1 1 calc R . .
H14 H 0.3956 0.7545 1.0249 0.052 Uiso 1 1 calc R . .
C5 C 0.2408(2) 0.6405(3) 0.8647(2) 0.0449(6) Uani 1 1 d . . .
H15 H 0.2435 0.5976 0.9498 0.054 Uiso 1 1 calc R . .
H16 H 0.2799 0.5817 0.8181 0.054 Uiso 1 1 calc R . .
C4 C 0.0789(2) 0.6666(3) 0.7567(2) 0.0406(5) Uani 1 1 d . . .
C3 C 0.0670(2) 0.7378(2) 0.6208(2) 0.0345(5) Uani 1 1 d . . .
H18 H 0.1166 0.8202 0.6522 0.041 Uiso 1 1 calc R . .
C16 C -0.1556(2) 0.7671(3) 0.3850(2) 0.0383(5) Uani 1 1 d . . .
C2 C 0.1306(2) 0.6693(3) 0.5325(2) 0.0350(5) Uani 1 1 d . . .
H19 H 0.0873 0.5852 0.5050 0.042 Uiso 1 1 calc R . .
H20 H 0.2357 0.6595 0.5906 0.042 Uiso 1 1 calc R . .
C18 C 0.0047(3) 0.7421(4) 0.8316(3) 0.0620(8) Uani 1 1 d . . .
H22 H -0.0968 0.7544 0.7643 0.093 Uiso 1 1 calc R . .
H21 H 0.0518 0.8235 0.8619 0.093 Uiso 1 1 calc R . .
H23 H 0.0125 0.6959 0.9158 0.093 Uiso 1 1 calc R . .
C20 C 0.4371(3) 0.9693(2) 0.2852(3) 0.0418(5) Uani 1 1 d . . .
H29 H 0.3648 1.0111 0.1994 0.063 Uiso 1 1 calc R . .
H28 H 0.4907 0.9093 0.2572 0.063 Uiso 1 1 calc R . .
H27 H 0.5035 1.0317 0.3503 0.063 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 C12 1.448(3) . ?
O1 H6 0.90(4) . ?
O2 C11 1.438(2) . ?
O2 H7 0.79(3) . ?
O3 C4 1.423(4) . ?
O3 H17 0.81(4) . ?
O4 C16 1.337(3) . ?
O4 C3 1.463(2) . ?
O5 C16 1.200(3) . ?
C19 C8 1.504(4) . ?
C19 H13 0.9600 . ?
C19 H12 0.9600 . ?
C19 H1 0.9600 . ?
C8 C7 1.336(3) . ?
C8 C9 1.513(3) . ?
C9 C10 1.542(3) . ?
C9 H11 0.9700 . ?
C9 H10 0.9700 . ?
C10 C11 1.523(3) . ?
C10 H26 0.9700 . ?
C10 H9 0.9700 . ?
C11 C12 1.545(3) . ?
C11 H8 0.9800 . ?
C12 C20 1.529(3) . ?
C12 C13 1.540(3) . ?
C13 C14 1.531(3) . ?
C13 H5 0.9700 . ?
C13 H4 0.9700 . ?
C14 C1 1.542(3) . ?
C14 H3 0.9700 . ?
C14 H30 0.9700 . ?
C1 C15 1.509(3) . ?
C1 C2 1.524(3) . ?
C1 H31 0.9800 . ?
C15 C17 1.306(3) . ?
C15 C16 1.488(3) . ?
C17 H2 0.9300 . ?
C17 H32 0.9300 . ?
C7 C6 1.503(3) . ?
C7 H25 0.9300 . ?
C6 C5 1.542(4) . ?
C6 H24 0.9700 . ?
C6 H14 0.9700 . ?
C5 C4 1.542(3) . ?
C5 H15 0.9700 . ?
C5 H16 0.9700 . ?
C4 C18 1.523(4) . ?
C4 C3 1.534(3) . ?
C3 C2 1.512(3) . ?
C3 H18 0.9800 . ?
C2 H19 0.9700 . ?
C2 H20 0.9700 . ?
C18 H22 0.9600 . ?
C18 H21 0.9600 . ?
C18 H23 0.9600 . ?
C20 H29 0.9600 . ?
C20 H28 0.9600 . ?
C20 H27 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
C12 O1 H6 109(2) . . ?
C11 O2 H7 115(3) . . ?
C4 O3 H17 101(3) . . ?
C16 O4 C3 124.10(16) . . ?
C8 C19 H13 109.5 . . ?
C8 C19 H12 109.5 . . ?
H13 C19 H12 109.5 . . ?
C8 C19 H1 109.5 . . ?
H13 C19 H1 109.5 . . ?
H12 C19 H1 109.5 . . ?
C7 C8 C19 122.9(2) . . ?
C7 C8 C9 120.9(2) . . ?
C19 C8 C9 116.1(2) . . ?
C8 C9 C10 114.18(18) . . ?
C8 C9 H11 108.7 . . ?
C10 C9 H11 108.7 . . ?
C8 C9 H10 108.7 . . ?
C10 C9 H10 108.7 . . ?
H11 C9 H10 107.6 . . ?
C11 C10 C9 111.98(18) . . ?
C11 C10 H26 109.2 . . ?
C9 C10 H26 109.2 . . ?
C11 C10 H9 109.2 . . ?
C9 C10 H9 109.2 . . ?
H26 C10 H9 107.9 . . ?
O2 C11 C10 111.26(16) . . ?
O2 C11 C12 110.91(15) . . ?
C10 C11 C12 115.37(18) . . ?
O2 C11 H8 106.2 . . ?
C10 C11 H8 106.2 . . ?
C12 C11 H8 106.2 . . ?
O1 C12 C20 108.16(19) . . ?
O1 C12 C13 108.05(16) . . ?
C20 C12 C13 109.04(17) . . ?
O1 C12 C11 107.28(16) . . ?
C20 C12 C11 112.62(17) . . ?
C13 C12 C11 111.52(19) . . ?
C14 C13 C12 118.10(17) . . ?
C14 C13 H5 107.8 . . ?
C12 C13 H5 107.8 . . ?
C14 C13 H4 107.8 . . ?
C12 C13 H4 107.8 . . ?
H5 C13 H4 107.1 . . ?
C13 C14 C1 115.71(19) . . ?
C13 C14 H3 108.4 . . ?
C1 C14 H3 108.4 . . ?
C13 C14 H30 108.4 . . ?
C1 C14 H30 108.4 . . ?
H3 C14 H30 107.4 . . ?
C15 C1 C2 107.49(16) . . ?
C15 C1 C14 115.33(17) . . ?
C2 C1 C14 113.04(18) . . ?
C15 C1 H31 106.8 . . ?
C2 C1 H31 106.8 . . ?
C14 C1 H31 106.8 . . ?
C17 C15 C16 116.4(2) . . ?
C17 C15 C1 126.8(2) . . ?
C16 C15 C1 116.82(18) . . ?
C15 C17 H2 120.0 . . ?
C15 C17 H32 120.0 . . ?
H2 C17 H32 120.0 . . ?
C8 C7 C6 128.0(2) . . ?
C8 C7 H25 116.0 . . ?
C6 C7 H25 116.0 . . ?
C7 C6 C5 114.7(2) . . ?
C7 C6 H24 108.6 . . ?
C5 C6 H24 108.6 . . ?
C7 C6 H14 108.6 . . ?
C5 C6 H14 108.6 . . ?
H24 C6 H14 107.6 . . ?
C6 C5 C4 117.2(2) . . ?
C6 C5 H15 108.0 . . ?
C4 C5 H15 108.0 . . ?
C6 C5 H16 108.0 . . ?
C4 C5 H16 108.0 . . ?
H15 C5 H16 107.3 . . ?
O3 C4 C18 111.1(2) . . ?
O3 C4 C3 110.0(2) . . ?
C18 C4 C3 110.5(2) . . ?
O3 C4 C5 103.8(2) . . ?
C18 C4 C5 110.5(2) . . ?
C3 C4 C5 110.70(17) . . ?
O4 C3 C2 110.67(16) . . ?
O4 C3 C4 105.17(15) . . ?
C2 C3 C4 115.6(2) . . ?
O4 C3 H18 108.4 . . ?
C2 C3 H18 108.4 . . ?
C4 C3 H18 108.4 . . ?
O5 C16 O4 117.07(19) . . ?
O5 C16 C15 123.5(2) . . ?
O4 C16 C15 119.42(18) . . ?
C3 C2 C1 108.52(19) . . ?
C3 C2 H19 110.0 . . ?
C1 C2 H19 110.0 . . ?
C3 C2 H20 110.0 . . ?
C1 C2 H20 110.0 . . ?
H19 C2 H20 108.4 . . ?
C4 C18 H22 109.5 . . ?
C4 C18 H21 109.5 . . ?
H22 C18 H21 109.5 . . ?
C4 C18 H23 109.5 . . ?
H22 C18 H23 109.5 . . ?
H21 C18 H23 109.5 . . ?
C12 C20 H29 109.5 . . ?
C12 C20 H28 109.5 . . ?
H29 C20 H28 109.5 . . ?
C12 C20 H27 109.5 . . ?
H29 C20 H27 109.5 . . ?
H28 C20 H27 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
C7 C8 C9 C10 124.8(2) . . . . ?
C19 C8 C9 C10 -57.0(3) . . . . ?
C8 C9 C10 C11 -66.7(3) . . . . ?
C9 C10 C11 O2 -86.8(2) . . . . ?
C9 C10 C11 C12 145.72(18) . . . . ?
O2 C11 C12 O1 173.89(15) . . . . ?
C10 C11 C12 O1 -58.5(2) . . . . ?
O2 C11 C12 C20 -67.2(2) . . . . ?
C10 C11 C12 C20 60.4(2) . . . . ?
O2 C11 C12 C13 55.8(2) . . . . ?
C10 C11 C12 C13 -176.60(16) . . . . ?
O1 C12 C13 C14 -79.4(2) . . . . ?
C20 C12 C13 C14 163.31(19) . . . . ?
C11 C12 C13 C14 38.3(2) . . . . ?
C12 C13 C14 C1 64.8(2) . . . . ?
C13 C14 C1 C15 96.0(2) . . . . ?
C13 C14 C1 C2 -139.8(2) . . . . ?
C2 C1 C15 C17 -139.8(4) . . . . ?
C14 C1 C15 C17 -12.8(4) . . . . ?
C2 C1 C15 C16 40.4(3) . . . . ?
C14 C1 C15 C16 167.5(2) . . . . ?
C19 C8 C7 C6 -3.9(3) . . . . ?
C9 C8 C7 C6 174.3(2) . . . . ?
C8 C7 C6 C5 140.2(2) . . . . ?
C7 C6 C5 C4 -110.1(2) . . . . ?
C6 C5 C4 O3 174.40(19) . . . . ?
C6 C5 C4 C18 -66.5(3) . . . . ?
C6 C5 C4 C3 56.4(3) . . . . ?
C16 O4 C3 C2 -23.5(3) . . . . ?
C16 O4 C3 C4 -149.0(2) . . . . ?
O3 C4 C3 O4 68.2(2) . . . . ?
C18 C4 C3 O4 -54.9(3) . . . . ?
C5 C4 C3 O4 -177.7(2) . . . . ?
O3 C4 C3 C2 -54.2(3) . . . . ?
C18 C4 C3 C2 -177.2(2) . . . . ?
C5 C4 C3 C2 60.0(3) . . . . ?
C3 O4 C16 O5 178.4(2) . . . . ?
C3 O4 C16 C15 -0.8(4) . . . . ?
C17 C15 C16 O5 -7.4(5) . . . . ?
C1 C15 C16 O5 172.3(3) . . . . ?
C17 C15 C16 O4 171.7(3) . . . . ?
C1 C15 C16 O4 -8.5(3) . . . . ?
O4 C3 C2 C1 55.8(2) . . . . ?
C4 C3 C2 C1 175.14(18) . . . . ?
C15 C1 C2 C3 -63.8(2) . . . . ?
C14 C1 C2 C3 167.75(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.953
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.090
####################################################################### 
# 
# 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_H:\Report\20120073\20120073.CIF
_database_code_depnum_ccdc_archive 'CCDC 1040659'
_audit_update_record             
;
2014-12-22 deposited with the CCDC.
2015-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Sinulaflexiolide L'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H66 O11'
_chemical_formula_weight         722.93

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2

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

_cell_length_a                   17.9396(13)
_cell_length_b                   8.5245(7)
_cell_length_c                   24.5138(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.789(8)
_cell_angle_gamma                90.00
_cell_volume                     3704.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6169
_cell_measurement_theta_min      4.50
_cell_measurement_theta_max      54.87

_exptl_crystal_description       Columnar
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1576
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6526
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26317
_diffrn_reflns_av_R_equivalents  0.0945
_diffrn_reflns_av_sigmaI/netI    0.1199
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         0.84
_diffrn_reflns_theta_max         24.82
_reflns_number_total             6362
_reflns_number_gt                4108
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_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)+(0.0500P)²+1.9704P] 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       0.0021(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   -0.4(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6362
_refine_ls_number_parameters     470
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.966
_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 0.86801(14) 0.7534(3) 0.71947(10) 0.0207(7) Uani 1 1 d . . .
O2 O 0.63405(14) 0.1660(3) 0.76859(10) 0.0209(7) Uani 1 1 d . . .
O3 O 0.93035(13) 0.8857(4) 0.59188(11) 0.0264(7) Uani 1 1 d . . .
H103 H 0.9741 0.9163 0.5942 0.040 Uiso 1 1 calc R . .
O4 O 0.81202(15) 0.8625(4) 0.78637(11) 0.0353(8) Uani 1 1 d . . .
O5 O 0.67109(14) 0.8412(3) 0.72190(11) 0.0220(7) Uani 1 1 d . . .
H108 H 0.6808 0.9304 0.7126 0.033 Uiso 1 1 calc R . .
O6 O 0.68965(14) 0.1885(3) 0.69592(10) 0.0223(7) Uani 1 1 d . . .
O7 O 0.64111(15) -0.1173(3) 0.83594(10) 0.0237(7) Uani 1 1 d . . .
H7A H 0.6507 -0.1230 0.8044 0.036 Uiso 1 1 calc R . .
O8 O 0.76864(15) 0.5513(4) 0.99847(11) 0.0299(8) Uani 1 1 d . . .
O9 O 0.57134(14) 0.4710(3) 0.57641(11) 0.0252(7) Uani 1 1 d . . .
H9 H 0.5592 0.5306 0.5503 0.038 Uiso 1 1 calc R . .
O10 O 0.67227(15) 0.5063(3) 0.50221(11) 0.0236(7) Uani 1 1 d . . .
H43 H 0.635(2) 0.460(5) 0.4877(17) 0.035 Uiso 1 1 d . . .
C1 C 0.9486(2) 0.3420(6) 0.64125(18) 0.0330(12) Uani 1 1 d . . .
H64 H 0.9240 0.3908 0.6690 0.049 Uiso 1 1 calc R . .
H3 H 0.9974 0.3050 0.6577 0.049 Uiso 1 1 calc R . .
H1 H 0.9188 0.2551 0.6254 0.049 Uiso 1 1 calc R . .
C2 C 0.9574(2) 0.4594(5) 0.59689(16) 0.0231(10) Uani 1 1 d . . .
C3 C 1.0177(2) 0.5798(5) 0.61204(17) 0.0269(11) Uani 1 1 d . . .
H63 H 1.0253 0.6376 0.5792 0.032 Uiso 1 1 calc R . .
H4 H 1.0647 0.5277 0.6263 0.032 Uiso 1 1 calc R . .
C4 C 0.9970(2) 0.6953(5) 0.65567(16) 0.0252(10) Uani 1 1 d . . .
H107 H 0.9924 0.6378 0.6891 0.030 Uiso 1 1 calc R . .
H6 H 1.0376 0.7706 0.6644 0.030 Uiso 1 1 calc R . .
C5 C 0.9236(2) 0.7838(5) 0.63689(15) 0.0200(10) Uani 1 1 d . . .
H8 H 0.8856 0.7050 0.6231 0.024 Uiso 1 1 calc R . .
C6 C 0.8924(2) 0.8752(5) 0.68241(15) 0.0202(10) Uani 1 1 d . . .
C7 C 0.8059(2) 0.7948(5) 0.74314(17) 0.0202(10) Uani 1 1 d . . .
C8 C 0.7302(2) 0.7368(5) 0.71189(15) 0.0170(9) Uani 1 1 d . . .
C9 C 0.7113(2) 0.5812(5) 0.74006(15) 0.0185(10) Uani 1 1 d . . .
H41 H 0.7007 0.6053 0.7768 0.022 Uiso 1 1 calc R . .
H10 H 0.6657 0.5375 0.7192 0.022 Uiso 1 1 calc R . .
C10 C 0.7734(2) 0.4562(5) 0.74492(15) 0.0182(9) Uani 1 1 d . . .
H11 H 0.8201 0.5023 0.7631 0.022 Uiso 1 1 calc R . .
H40 H 0.7810 0.4254 0.7081 0.022 Uiso 1 1 calc R . .
C11 C 0.7566(2) 0.3080(5) 0.77704(15) 0.0171(9) Uani 1 1 d . . .
H39 H 0.8006 0.2401 0.7765 0.021 Uiso 1 1 calc R . .
C12 C 0.6916(2) 0.2189(5) 0.74484(16) 0.0186(10) Uani 1 1 d . . .
C13 C 0.6347(2) 0.1673(5) 0.82899(14) 0.0168(9) Uani 1 1 d . . .
H36 H 0.6048 0.2569 0.8384 0.020 Uiso 1 1 calc R . .
C14 C 0.5933(2) 0.0146(5) 0.84032(16) 0.0205(10) Uani 1 1 d . . .
C15 C 0.5760(2) 0.0081(5) 0.89967(15) 0.0223(10) Uani 1 1 d . . .
H18 H 0.6231 0.0216 0.9246 0.027 Uiso 1 1 calc R . .
H17 H 0.5573 -0.0960 0.9060 0.027 Uiso 1 1 calc R . .
C16 C 0.5189(2) 0.1289(5) 0.91551(17) 0.0257(11) Uani 1 1 d . . .
H19 H 0.4842 0.1555 0.8825 0.031 Uiso 1 1 calc R . .
H35 H 0.4897 0.0788 0.9408 0.031 Uiso 1 1 calc R . .
C17 C 0.5506(2) 0.2770(5) 0.94128(17) 0.0241(10) Uani 1 1 d . . .
H20 H 0.5862 0.2644 0.9728 0.029 Uiso 1 1 calc R . .
C18 C 0.5358(2) 0.4250(5) 0.92599(17) 0.0256(11) Uani 1 1 d . . .
C19 C 0.4836(2) 0.4721(6) 0.87497(18) 0.0395(13) Uani 1 1 d . . .
H22 H 0.4699 0.3811 0.8526 0.059 Uiso 1 1 calc R . .
H21 H 0.5085 0.5465 0.8545 0.059 Uiso 1 1 calc R . .
H2 H 0.4391 0.5189 0.8851 0.059 Uiso 1 1 calc R . .
C20 C 0.7515(2) 0.3304(5) 0.83862(14) 0.0169(9) Uani 1 1 d . . .
H38 H 0.7191 0.4212 0.8423 0.020 Uiso 1 1 calc R . .
C21 C 0.7138(2) 0.1847(5) 0.85872(15) 0.0205(9) Uani 1 1 d . . .
H12 H 0.7428 0.0923 0.8524 0.025 Uiso 1 1 calc R . .
H37 H 0.7130 0.1932 0.8981 0.025 Uiso 1 1 calc R . .
C22 C 0.5205(2) -0.0075(5) 0.79920(16) 0.0275(11) Uani 1 1 d . . .
H14 H 0.5329 -0.0313 0.7634 0.041 Uiso 1 1 calc R . .
H16 H 0.4912 0.0872 0.7972 0.041 Uiso 1 1 calc R . .
H15 H 0.4917 -0.0923 0.8113 0.041 Uiso 1 1 calc R . .
C23 C 0.5733(2) 0.5610(5) 0.96034(18) 0.0312(11) Uani 1 1 d . . .
H33 H 0.5372 0.6460 0.9598 0.037 Uiso 1 1 calc R . .
H34 H 0.5865 0.5267 0.9983 0.037 Uiso 1 1 calc R . .
C24 C 0.6439(2) 0.6228(5) 0.94009(17) 0.0299(11) Uani 1 1 d . . .
H24 H 0.6337 0.6376 0.9004 0.036 Uiso 1 1 calc R . .
H23 H 0.6574 0.7238 0.9570 0.036 Uiso 1 1 calc R . .
C25 C 0.7089(2) 0.5107(5) 0.95414(16) 0.0261(10) Uani 1 1 d . . .
H32 H 0.6945 0.3997 0.9529 0.031 Uiso 1 1 calc R . .
C26 C 0.7846(2) 0.5414(5) 0.94205(15) 0.0225(10) Uani 1 1 d . . .
C27 C 0.8032(3) 0.6970(5) 0.91746(17) 0.0327(11) Uani 1 1 d . . .
H26 H 0.7763 0.7795 0.9326 0.049 Uiso 1 1 calc R . .
H27 H 0.7888 0.6939 0.8781 0.049 Uiso 1 1 calc R . .
H25 H 0.8565 0.7161 0.9261 0.049 Uiso 1 1 calc R . .
C28 C 0.8322(2) 0.4015(5) 0.93221(15) 0.0237(10) Uani 1 1 d . . .
H28 H 0.8147 0.3108 0.9506 0.028 Uiso 1 1 calc R . .
H29 H 0.8840 0.4215 0.9486 0.028 Uiso 1 1 calc R . .
C29 C 0.8299(2) 0.3637(5) 0.87128(15) 0.0219(10) Uani 1 1 d . . .
H30 H 0.8616 0.2728 0.8683 0.026 Uiso 1 1 calc R . .
H31 H 0.8518 0.4511 0.8540 0.026 Uiso 1 1 calc R . .
C30 C 0.7346(2) 0.7222(4) 0.65003(14) 0.0147(9) Uani 1 1 d . . .
H59 H 0.7739 0.6450 0.6462 0.018 Uiso 1 1 calc R . .
C31 C 0.6611(2) 0.6648(5) 0.61384(15) 0.0169(9) Uani 1 1 d . . .
H54 H 0.6196 0.6939 0.6329 0.020 Uiso 1 1 calc R . .
H53 H 0.6554 0.7251 0.5799 0.020 Uiso 1 1 calc R . .
C32 C 0.6502(2) 0.4919(5) 0.59756(15) 0.0169(9) Uani 1 1 d . . .
H52 H 0.6622 0.4283 0.6311 0.020 Uiso 1 1 calc R . .
C33 C 0.6962(2) 0.4276(5) 0.55391(15) 0.0181(10) Uani 1 1 d . . .
C34 C 0.7796(2) 0.4633(5) 0.56960(15) 0.0208(10) Uani 1 1 d . . .
H48 H 0.7942 0.4343 0.6080 0.025 Uiso 1 1 calc R . .
H47 H 0.7860 0.5760 0.5673 0.025 Uiso 1 1 calc R . .
C35 C 0.8355(2) 0.3856(5) 0.53635(16) 0.0258(10) Uani 1 1 d . . .
H46 H 0.8415 0.2754 0.5460 0.031 Uiso 1 1 calc R . .
H45 H 0.8171 0.3936 0.4971 0.031 Uiso 1 1 calc R . .
C36 C 0.9097(2) 0.4696(5) 0.55017(17) 0.0240(10) Uani 1 1 d . . .
H44 H 0.9234 0.5354 0.5231 0.029 Uiso 1 1 calc R . .
C37 C 0.6820(2) 0.2528(5) 0.54790(16) 0.0260(10) Uani 1 1 d . . .
H49 H 0.6290 0.2344 0.5369 0.039 Uiso 1 1 calc R . .
H50 H 0.6985 0.2019 0.5826 0.039 Uiso 1 1 calc R . .
H51 H 0.7093 0.2114 0.5204 0.039 Uiso 1 1 calc R . .
C38 C 0.7583(2) 0.8771(5) 0.62564(15) 0.0174(9) Uani 1 1 d . . .
H57 H 0.7143 0.9447 0.6195 0.021 Uiso 1 1 calc R . .
H58 H 0.7720 0.8541 0.5897 0.021 Uiso 1 1 calc R . .
C39 C 0.8233(2) 0.9715(5) 0.65863(16) 0.0213(10) Uani 1 1 d . . .
H55 H 0.8390 1.0517 0.6347 0.026 Uiso 1 1 calc R . .
H56 H 0.8044 1.0244 0.6888 0.026 Uiso 1 1 calc R . .
C40 C 0.9515(2) 0.9767(5) 0.71678(16) 0.0269(11) Uani 1 1 d . . .
H62 H 0.9280 1.0388 0.7420 0.040 Uiso 1 1 calc R . .
H61 H 0.9745 1.0446 0.6929 0.040 Uiso 1 1 calc R . .
H60 H 0.9894 0.9109 0.7371 0.040 Uiso 1 1 calc R . .
O11 O 0.5000 0.6947(5) 0.5000 0.0291(10) Uani 1 2 d S . .


_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 C7 1.379(5) . ?
O1 C6 1.488(5) . ?
O2 C12 1.338(5) . ?
O2 C13 1.479(4) . ?
O3 C5 1.424(4) . ?
O3 H103 0.8200 . ?
O4 C7 1.197(5) . ?
O5 C8 1.434(4) . ?
O5 H108 0.8200 . ?
O6 C12 1.222(4) . ?
O7 C14 1.429(5) . ?
O7 H7A 0.8200 . ?
O8 C25 1.447(4) . ?
O8 C26 1.457(5) . ?
O9 C32 1.441(4) . ?
O9 H9 0.8200 . ?
O10 C33 1.440(4) . ?
O10 H43 0.81(4) . ?
C1 C2 1.504(6) . ?
C1 H64 0.9600 . ?
C1 H3 0.9600 . ?
C1 H1 0.9600 . ?
C2 C36 1.324(5) . ?
C2 C3 1.496(6) . ?
C3 C4 1.540(6) . ?
C3 H63 0.9700 . ?
C3 H4 0.9700 . ?
C4 C5 1.526(5) . ?
C4 H107 0.9700 . ?
C4 H6 0.9700 . ?
C5 C6 1.535(5) . ?
C5 H8 0.9800 . ?
C6 C40 1.520(5) . ?
C6 C39 1.525(5) . ?
C7 C8 1.535(5) . ?
C8 C30 1.536(5) . ?
C8 C9 1.557(5) . ?
C9 C10 1.534(5) . ?
C9 H41 0.9700 . ?
C9 H10 0.9700 . ?
C10 C11 1.543(5) . ?
C10 H11 0.9700 . ?
C10 H40 0.9700 . ?
C11 C12 1.509(5) . ?
C11 C20 1.538(5) . ?
C11 H39 0.9800 . ?
C13 C21 1.501(5) . ?
C13 C14 1.544(6) . ?
C13 H36 0.9800 . ?
C14 C15 1.534(5) . ?
C14 C22 1.535(5) . ?
C15 C16 1.544(6) . ?
C15 H18 0.9700 . ?
C15 H17 0.9700 . ?
C16 C17 1.486(6) . ?
C16 H19 0.9700 . ?
C16 H35 0.9700 . ?
C17 C18 1.332(6) . ?
C17 H20 0.9300 . ?
C18 C19 1.498(6) . ?
C18 C23 1.527(6) . ?
C19 H22 0.9600 . ?
C19 H21 0.9600 . ?
C19 H2 0.9600 . ?
C20 C21 1.531(5) . ?
C20 C29 1.536(5) . ?
C20 H38 0.9800 . ?
C21 H12 0.9700 . ?
C21 H37 0.9700 . ?
C22 H14 0.9600 . ?
C22 H16 0.9600 . ?
C22 H15 0.9600 . ?
C23 C24 1.524(6) . ?
C23 H33 0.9700 . ?
C23 H34 0.9700 . ?
C24 C25 1.506(6) . ?
C24 H24 0.9700 . ?
C24 H23 0.9700 . ?
C25 C26 1.457(5) . ?
C25 H32 0.9800 . ?
C26 C28 1.508(6) . ?
C26 C27 1.515(6) . ?
C27 H26 0.9600 . ?
C27 H27 0.9600 . ?
C27 H25 0.9600 . ?
C28 C29 1.522(5) . ?
C28 H28 0.9700 . ?
C28 H29 0.9700 . ?
C29 H30 0.9700 . ?
C29 H31 0.9700 . ?
C30 C38 1.535(5) . ?
C30 C31 1.551(5) . ?
C30 H59 0.9800 . ?
C31 C32 1.532(6) . ?
C31 H54 0.9700 . ?
C31 H53 0.9700 . ?
C32 C33 1.549(5) . ?
C32 H52 0.9800 . ?
C33 C37 1.515(6) . ?
C33 C34 1.517(5) . ?
C34 C35 1.536(5) . ?
C34 H48 0.9700 . ?
C34 H47 0.9700 . ?
C35 C36 1.503(5) . ?
C35 H46 0.9700 . ?
C35 H45 0.9700 . ?
C36 H44 0.9300 . ?
C37 H49 0.9600 . ?
C37 H50 0.9600 . ?
C37 H51 0.9600 . ?
C38 C39 1.542(5) . ?
C38 H57 0.9700 . ?
C38 H58 0.9700 . ?
C39 H55 0.9700 . ?
C39 H56 0.9700 . ?
C40 H62 0.9600 . ?
C40 H61 0.9600 . ?
C40 H60 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
C7 O1 C6 114.2(3) . . ?
C12 O2 C13 123.0(3) . . ?
C5 O3 H103 109.5 . . ?
C8 O5 H108 109.5 . . ?
C14 O7 H7A 109.5 . . ?
C25 O8 C26 60.2(2) . . ?
C32 O9 H9 109.5 . . ?
C33 O10 H43 106(3) . . ?
C2 C1 H64 109.5 . . ?
C2 C1 H3 109.5 . . ?
H64 C1 H3 109.5 . . ?
C2 C1 H1 109.5 . . ?
H64 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
C36 C2 C3 121.1(4) . . ?
C36 C2 C1 122.9(4) . . ?
C3 C2 C1 115.4(3) . . ?
C2 C3 C4 111.7(3) . . ?
C2 C3 H63 109.3 . . ?
C4 C3 H63 109.3 . . ?
C2 C3 H4 109.3 . . ?
C4 C3 H4 109.3 . . ?
H63 C3 H4 107.9 . . ?
C5 C4 C3 113.3(3) . . ?
C5 C4 H107 108.9 . . ?
C3 C4 H107 108.9 . . ?
C5 C4 H6 108.9 . . ?
C3 C4 H6 108.9 . . ?
H107 C4 H6 107.7 . . ?
O3 C5 C4 111.3(3) . . ?
O3 C5 C6 109.7(3) . . ?
C4 C5 C6 115.2(3) . . ?
O3 C5 H8 106.7 . . ?
C4 C5 H8 106.7 . . ?
C6 C5 H8 106.7 . . ?
O1 C6 C40 107.7(3) . . ?
O1 C6 C39 108.2(3) . . ?
C40 C6 C39 111.2(4) . . ?
O1 C6 C5 105.3(3) . . ?
C40 C6 C5 113.0(3) . . ?
C39 C6 C5 111.1(3) . . ?
O4 C7 O1 121.7(4) . . ?
O4 C7 C8 123.5(4) . . ?
O1 C7 C8 114.7(3) . . ?
O5 C8 C7 109.6(3) . . ?
O5 C8 C30 111.7(3) . . ?
C7 C8 C30 110.1(3) . . ?
O5 C8 C9 103.6(3) . . ?
C7 C8 C9 106.8(3) . . ?
C30 C8 C9 114.6(3) . . ?
C10 C9 C8 114.9(3) . . ?
C10 C9 H41 108.5 . . ?
C8 C9 H41 108.5 . . ?
C10 C9 H10 108.5 . . ?
C8 C9 H10 108.5 . . ?
H41 C9 H10 107.5 . . ?
C9 C10 C11 114.4(3) . . ?
C9 C10 H11 108.7 . . ?
C11 C10 H11 108.7 . . ?
C9 C10 H40 108.7 . . ?
C11 C10 H40 108.7 . . ?
H11 C10 H40 107.6 . . ?
C12 C11 C20 114.7(3) . . ?
C12 C11 C10 109.9(3) . . ?
C20 C11 C10 116.4(3) . . ?
C12 C11 H39 104.8 . . ?
C20 C11 H39 104.8 . . ?
C10 C11 H39 104.8 . . ?
O6 C12 O2 116.5(4) . . ?
O6 C12 C11 121.6(4) . . ?
O2 C12 C11 121.9(3) . . ?
O2 C13 C21 110.4(3) . . ?
O2 C13 C14 104.1(3) . . ?
C21 C13 C14 116.2(3) . . ?
O2 C13 H36 108.6 . . ?
C21 C13 H36 108.6 . . ?
C14 C13 H36 108.6 . . ?
O7 C14 C15 104.7(3) . . ?
O7 C14 C22 108.3(3) . . ?
C15 C14 C22 110.1(3) . . ?
O7 C14 C13 109.8(3) . . ?
C15 C14 C13 111.9(3) . . ?
C22 C14 C13 111.7(3) . . ?
C14 C15 C16 116.9(3) . . ?
C14 C15 H18 108.1 . . ?
C16 C15 H18 108.1 . . ?
C14 C15 H17 108.1 . . ?
C16 C15 H17 108.1 . . ?
H18 C15 H17 107.3 . . ?
C17 C16 C15 116.6(3) . . ?
C17 C16 H19 108.2 . . ?
C15 C16 H19 108.2 . . ?
C17 C16 H35 108.2 . . ?
C15 C16 H35 108.2 . . ?
H19 C16 H35 107.3 . . ?
C18 C17 C16 129.7(4) . . ?
C18 C17 H20 115.2 . . ?
C16 C17 H20 115.2 . . ?
C17 C18 C19 124.2(4) . . ?
C17 C18 C23 120.8(4) . . ?
C19 C18 C23 115.0(4) . . ?
C18 C19 H22 109.5 . . ?
C18 C19 H21 109.5 . . ?
H22 C19 H21 109.5 . . ?
C18 C19 H2 109.5 . . ?
H22 C19 H2 109.5 . . ?
H21 C19 H2 109.5 . . ?
C21 C20 C29 113.4(3) . . ?
C21 C20 C11 108.1(3) . . ?
C29 C20 C11 110.3(3) . . ?
C21 C20 H38 108.3 . . ?
C29 C20 H38 108.3 . . ?
C11 C20 H38 108.3 . . ?
C13 C21 C20 110.8(3) . . ?
C13 C21 H12 109.5 . . ?
C20 C21 H12 109.5 . . ?
C13 C21 H37 109.5 . . ?
C20 C21 H37 109.5 . . ?
H12 C21 H37 108.1 . . ?
C14 C22 H14 109.5 . . ?
C14 C22 H16 109.5 . . ?
H14 C22 H16 109.5 . . ?
C14 C22 H15 109.5 . . ?
H14 C22 H15 109.5 . . ?
H16 C22 H15 109.5 . . ?
C24 C23 C18 113.6(3) . . ?
C24 C23 H33 108.8 . . ?
C18 C23 H33 108.8 . . ?
C24 C23 H34 108.8 . . ?
C18 C23 H34 108.8 . . ?
H33 C23 H34 107.7 . . ?
C25 C24 C23 111.1(4) . . ?
C25 C24 H24 109.4 . . ?
C23 C24 H24 109.4 . . ?
C25 C24 H23 109.4 . . ?
C23 C24 H23 109.4 . . ?
H24 C24 H23 108.0 . . ?
O8 C25 C26 60.2(2) . . ?
O8 C25 C24 118.6(4) . . ?
C26 C25 C24 123.5(4) . . ?
O8 C25 H32 114.5 . . ?
C26 C25 H32 114.5 . . ?
C24 C25 H32 114.5 . . ?
O8 C26 C25 59.6(2) . . ?
O8 C26 C28 113.3(3) . . ?
C25 C26 C28 117.3(4) . . ?
O8 C26 C27 114.5(3) . . ?
C25 C26 C27 120.5(4) . . ?
C28 C26 C27 117.6(4) . . ?
C26 C27 H26 109.5 . . ?
C26 C27 H27 109.5 . . ?
H26 C27 H27 109.5 . . ?
C26 C27 H25 109.5 . . ?
H26 C27 H25 109.5 . . ?
H27 C27 H25 109.5 . . ?
C26 C28 C29 113.2(3) . . ?
C26 C28 H28 108.9 . . ?
C29 C28 H28 108.9 . . ?
C26 C28 H29 108.9 . . ?
C29 C28 H29 108.9 . . ?
H28 C28 H29 107.8 . . ?
C28 C29 C20 115.8(3) . . ?
C28 C29 H30 108.3 . . ?
C20 C29 H30 108.3 . . ?
C28 C29 H31 108.3 . . ?
C20 C29 H31 108.3 . . ?
H30 C29 H31 107.4 . . ?
C38 C30 C8 111.9(3) . . ?
C38 C30 C31 108.0(3) . . ?
C8 C30 C31 115.0(3) . . ?
C38 C30 H59 107.1 . . ?
C8 C30 H59 107.1 . . ?
C31 C30 H59 107.1 . . ?
C32 C31 C30 121.1(3) . . ?
C32 C31 H54 107.1 . . ?
C30 C31 H54 107.1 . . ?
C32 C31 H53 107.1 . . ?
C30 C31 H53 107.1 . . ?
H54 C31 H53 106.8 . . ?
O9 C32 C31 107.0(3) . . ?
O9 C32 C33 107.8(3) . . ?
C31 C32 C33 117.4(3) . . ?
O9 C32 H52 108.1 . . ?
C31 C32 H52 108.1 . . ?
C33 C32 H52 108.1 . . ?
O10 C33 C37 110.4(3) . . ?
O10 C33 C34 106.2(3) . . ?
C37 C33 C34 111.6(3) . . ?
O10 C33 C32 108.9(3) . . ?
C37 C33 C32 108.4(3) . . ?
C34 C33 C32 111.3(3) . . ?
C33 C34 C35 118.5(3) . . ?
C33 C34 H48 107.7 . . ?
C35 C34 H48 107.7 . . ?
C33 C34 H47 107.7 . . ?
C35 C34 H47 107.7 . . ?
H48 C34 H47 107.1 . . ?
C36 C35 C34 107.6(3) . . ?
C36 C35 H46 110.2 . . ?
C34 C35 H46 110.2 . . ?
C36 C35 H45 110.2 . . ?
C34 C35 H45 110.2 . . ?
H46 C35 H45 108.5 . . ?
C2 C36 C35 126.7(4) . . ?
C2 C36 H44 116.7 . . ?
C35 C36 H44 116.7 . . ?
C33 C37 H49 109.5 . . ?
C33 C37 H50 109.5 . . ?
H49 C37 H50 109.5 . . ?
C33 C37 H51 109.5 . . ?
H49 C37 H51 109.5 . . ?
H50 C37 H51 109.5 . . ?
C30 C38 C39 118.5(3) . . ?
C30 C38 H57 107.7 . . ?
C39 C38 H57 107.7 . . ?
C30 C38 H58 107.7 . . ?
C39 C38 H58 107.7 . . ?
H57 C38 H58 107.1 . . ?
C6 C39 C38 115.1(3) . . ?
C6 C39 H55 108.5 . . ?
C38 C39 H55 108.5 . . ?
C6 C39 H56 108.5 . . ?
C38 C39 H56 108.5 . . ?
H55 C39 H56 107.5 . . ?
C6 C40 H62 109.5 . . ?
C6 C40 H61 109.5 . . ?
H62 C40 H61 109.5 . . ?
C6 C40 H60 109.5 . . ?
H62 C40 H60 109.5 . . ?
H61 C40 H60 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
C36 C2 C3 C4 102.7(5) . . . . ?
C1 C2 C3 C4 -69.2(5) . . . . ?
C2 C3 C4 C5 -59.1(5) . . . . ?
C3 C4 C5 O3 -65.9(4) . . . . ?
C3 C4 C5 C6 168.4(3) . . . . ?
C7 O1 C6 C40 92.4(4) . . . . ?
C7 O1 C6 C39 -27.9(4) . . . . ?
C7 O1 C6 C5 -146.8(3) . . . . ?
O3 C5 C6 O1 165.0(3) . . . . ?
C4 C5 C6 O1 -68.4(4) . . . . ?
O3 C5 C6 C40 -77.7(4) . . . . ?
C4 C5 C6 C40 48.8(5) . . . . ?
O3 C5 C6 C39 48.1(4) . . . . ?
C4 C5 C6 C39 174.7(3) . . . . ?
C6 O1 C7 O4 -89.5(4) . . . . ?
C6 O1 C7 C8 94.7(4) . . . . ?
O4 C7 C8 O5 32.1(5) . . . . ?
O1 C7 C8 O5 -152.2(3) . . . . ?
O4 C7 C8 C30 155.4(4) . . . . ?
O1 C7 C8 C30 -28.9(4) . . . . ?
O4 C7 C8 C9 -79.6(5) . . . . ?
O1 C7 C8 C9 96.2(4) . . . . ?
O5 C8 C9 C10 -169.4(3) . . . . ?
C7 C8 C9 C10 -53.7(4) . . . . ?
C30 C8 C9 C10 68.6(4) . . . . ?
C8 C9 C10 C11 175.3(3) . . . . ?
C9 C10 C11 C12 67.6(4) . . . . ?
C9 C10 C11 C20 -64.9(4) . . . . ?
C13 O2 C12 O6 168.5(3) . . . . ?
C13 O2 C12 C11 -10.0(5) . . . . ?
C20 C11 C12 O6 -177.7(4) . . . . ?
C10 C11 C12 O6 48.9(5) . . . . ?
C20 C11 C12 O2 0.7(5) . . . . ?
C10 C11 C12 O2 -132.7(3) . . . . ?
C12 O2 C13 C21 -18.1(5) . . . . ?
C12 O2 C13 C14 -143.4(3) . . . . ?
O2 C13 C14 O7 74.0(3) . . . . ?
C21 C13 C14 O7 -47.5(4) . . . . ?
O2 C13 C14 C15 -170.2(3) . . . . ?
C21 C13 C14 C15 68.3(4) . . . . ?
O2 C13 C14 C22 -46.2(4) . . . . ?
C21 C13 C14 C22 -167.8(3) . . . . ?
O7 C14 C15 C16 -174.6(3) . . . . ?
C22 C14 C15 C16 -58.3(5) . . . . ?
C13 C14 C15 C16 66.5(4) . . . . ?
C14 C15 C16 C17 -93.6(4) . . . . ?
C15 C16 C17 C18 124.3(5) . . . . ?
C16 C17 C18 C19 -3.4(7) . . . . ?
C16 C17 C18 C23 177.5(4) . . . . ?
C12 C11 C20 C21 34.3(4) . . . . ?
C10 C11 C20 C21 164.6(3) . . . . ?
C12 C11 C20 C29 158.7(3) . . . . ?
C10 C11 C20 C29 -70.9(4) . . . . ?
O2 C13 C21 C20 54.9(4) . . . . ?
C14 C13 C21 C20 173.1(3) . . . . ?
C29 C20 C21 C13 174.5(3) . . . . ?
C11 C20 C21 C13 -62.9(4) . . . . ?
C17 C18 C23 C24 95.4(5) . . . . ?
C19 C18 C23 C24 -83.8(4) . . . . ?
C18 C23 C24 C25 -73.7(5) . . . . ?
C26 O8 C25 C24 -114.4(5) . . . . ?
C23 C24 C25 O8 -105.8(4) . . . . ?
C23 C24 C25 C26 -177.3(4) . . . . ?
C25 O8 C26 C28 -109.0(4) . . . . ?
C25 O8 C26 C27 112.3(4) . . . . ?
C24 C25 C26 O8 106.4(4) . . . . ?
O8 C25 C26 C28 102.3(4) . . . . ?
C24 C25 C26 C28 -151.3(4) . . . . ?
O8 C25 C26 C27 -102.2(4) . . . . ?
C24 C25 C26 C27 4.2(6) . . . . ?
O8 C26 C28 C29 163.2(3) . . . . ?
C25 C26 C28 C29 96.7(4) . . . . ?
C27 C26 C28 C29 -59.5(5) . . . . ?
C26 C28 C29 C20 -58.0(5) . . . . ?
C21 C20 C29 C28 -63.4(5) . . . . ?
C11 C20 C29 C28 175.2(4) . . . . ?
O5 C8 C30 C38 66.1(4) . . . . ?
C7 C8 C30 C38 -56.0(4) . . . . ?
C9 C8 C30 C38 -176.5(3) . . . . ?
O5 C8 C30 C31 -57.8(4) . . . . ?
C7 C8 C30 C31 -179.8(3) . . . . ?
C9 C8 C30 C31 59.7(4) . . . . ?
C38 C30 C31 C32 137.3(3) . . . . ?
C8 C30 C31 C32 -96.9(4) . . . . ?
C30 C31 C32 O9 166.2(3) . . . . ?
C30 C31 C32 C33 -72.6(4) . . . . ?
O9 C32 C33 O10 56.1(4) . . . . ?
C31 C32 C33 O10 -64.7(4) . . . . ?
O9 C32 C33 C37 -64.1(4) . . . . ?
C31 C32 C33 C37 175.1(3) . . . . ?
O9 C32 C33 C34 172.9(3) . . . . ?
C31 C32 C33 C34 52.1(4) . . . . ?
O10 C33 C34 C35 -71.5(4) . . . . ?
C37 C33 C34 C35 48.9(5) . . . . ?
C32 C33 C34 C35 170.1(3) . . . . ?
C33 C34 C35 C36 166.0(3) . . . . ?
C3 C2 C36 C35 -162.6(4) . . . . ?
C1 C2 C36 C35 8.7(7) . . . . ?
C34 C35 C36 C2 73.1(5) . . . . ?
C8 C30 C38 C39 43.7(5) . . . . ?
C31 C30 C38 C39 171.3(3) . . . . ?
O1 C6 C39 C38 -58.8(4) . . . . ?
C40 C6 C39 C38 -176.8(3) . . . . ?
C5 C6 C39 C38 56.4(4) . . . . ?
C30 C38 C39 C6 45.5(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.82
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.054
