# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
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#  from this site to visualise CIF-encoded structures and 
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data_compound_10a

_database_code_depnum_ccdc_archive 'CCDC 1002242'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H33 Br O4'
_chemical_formula_weight         501.44
_chemical_absolute_configuration ad

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   11.718(16)
_cell_length_b                   8.241(11)
_cell_length_c                   13.602(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.699(13)
_cell_angle_gamma                90.00
_cell_volume                     1251(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1149
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      19.30

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_absorpt_coefficient_mu    1.672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6997
_exptl_absorpt_correction_T_max  0.7418
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6336
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.1329
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4296
_reflns_number_gt                2333
_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)+(0.0000P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.008(14)
_refine_ls_number_reflns         4296
_refine_ls_number_parameters     293
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1214
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1278
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_restrained_S_all      0.923
_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
Br1 Br 0.01519(6) 0.62764(12) -0.36871(4) 0.0876(3) Uani 1 1 d . . .
C1 C 0.2679(4) 0.1134(10) 0.6652(4) 0.0530(14) Uani 1 1 d . . .
H1A H 0.2778 0.0644 0.6035 0.064 Uiso 1 1 calc R . .
H1B H 0.1942 0.1756 0.6449 0.064 Uiso 1 1 calc R . .
C2 C 0.2568(6) -0.0223(8) 0.7396(5) 0.066(2) Uani 1 1 d . . .
H2A H 0.2379 0.0250 0.7981 0.079 Uiso 1 1 calc R . .
H2B H 0.1918 -0.0946 0.7045 0.079 Uiso 1 1 calc R . .
C3 C 0.3719(6) -0.1175(8) 0.7772(5) 0.063(2) Uani 1 1 d . . .
H3A H 0.3865 -0.1708 0.7186 0.075 Uiso 1 1 calc R . .
H3B H 0.3619 -0.2015 0.8239 0.075 Uiso 1 1 calc R . .
C4 C 0.4809(5) -0.0166(7) 0.8321(4) 0.0500(16) Uani 1 1 d . . .
C5 C 0.4883(4) 0.1275(10) 0.7619(3) 0.0411(12) Uani 1 1 d . . .
H5 H 0.5069 0.0771 0.7033 0.049 Uiso 1 1 calc R . .
C6 C 0.5949(5) 0.2389(8) 0.8098(4) 0.0525(16) Uani 1 1 d . . .
H6A H 0.5903 0.2780 0.8757 0.063 Uiso 1 1 calc R . .
H6B H 0.6684 0.1771 0.8224 0.063 Uiso 1 1 calc R . .
C7 C 0.5990(5) 0.3808(8) 0.7426(4) 0.0560(17) Uani 1 1 d . . .
H7 H 0.6668 0.4464 0.7614 0.067 Uiso 1 1 calc R . .
C8 C 0.5126(4) 0.4186(7) 0.6585(4) 0.0399(14) Uani 1 1 d . . .
C9 C 0.3979(4) 0.3238(6) 0.6229(3) 0.0365(13) Uani 1 1 d . . .
H9 H 0.4094 0.2426 0.5741 0.044 Uiso 1 1 calc R . .
C10 C 0.3722(5) 0.2280(6) 0.7114(4) 0.0366(13) Uani 1 1 d . . .
C11 C 0.2990(4) 0.4348(7) 0.5616(4) 0.0416(14) Uani 1 1 d . . .
H11A H 0.2257 0.3731 0.5342 0.050 Uiso 1 1 calc R . .
H11B H 0.2846 0.5187 0.6064 0.050 Uiso 1 1 calc R . .
C12 C 0.3332(5) 0.5118(7) 0.4741(4) 0.0432(15) Uani 1 1 d . . .
H12 H 0.3484 0.4254 0.4302 0.052 Uiso 1 1 calc R . .
C13 C 0.2401(4) 0.6250(10) 0.4078(3) 0.0457(12) Uani 1 1 d . . .
C14 C 0.1749(5) 0.5767(8) 0.3159(4) 0.0601(19) Uani 1 1 d . . .
H14 H 0.1998 0.4823 0.2910 0.072 Uiso 1 1 calc R . .
C15 C 0.0670(5) 0.6547(12) 0.2479(4) 0.080(2) Uani 1 1 d . . .
H15A H -0.0040 0.5970 0.2511 0.096 Uiso 1 1 calc R . .
H15B H 0.0619 0.7658 0.2697 0.096 Uiso 1 1 calc R . .
C16 C 0.2229(6) 0.7818(8) 0.4561(4) 0.0678(19) Uani 1 1 d . . .
H16A H 0.2887 0.8531 0.4591 0.102 Uiso 1 1 calc R . .
H16B H 0.2195 0.7621 0.5248 0.102 Uiso 1 1 calc R . .
H16C H 0.1494 0.8313 0.4157 0.102 Uiso 1 1 calc R . .
C17 C 0.5311(5) 0.5642(8) 0.5989(4) 0.0518(17) Uani 1 1 d . . .
C18 C 0.5926(6) -0.1250(8) 0.8504(5) 0.074(2) Uani 1 1 d . . .
H18A H 0.5807 -0.2243 0.8830 0.111 Uiso 1 1 calc R . .
H18B H 0.6612 -0.0693 0.8942 0.111 Uiso 1 1 calc R . .
H18C H 0.6054 -0.1491 0.7855 0.111 Uiso 1 1 calc R . .
C19 C 0.4715(6) 0.0321(8) 0.9393(4) 0.068(2) Uani 1 1 d . . .
H19A H 0.4008 0.0966 0.9306 0.102 Uiso 1 1 calc R . .
H19B H 0.5409 0.0939 0.9758 0.102 Uiso 1 1 calc R . .
H19C H 0.4669 -0.0639 0.9779 0.102 Uiso 1 1 calc R . .
C20 C 0.3404(6) 0.3448(8) 0.7864(4) 0.0548(19) Uani 1 1 d . . .
H20A H 0.2707 0.4063 0.7503 0.082 Uiso 1 1 calc R . .
H20B H 0.4063 0.4172 0.8151 0.082 Uiso 1 1 calc R . .
H20C H 0.3242 0.2841 0.8410 0.082 Uiso 1 1 calc R . .
C21 C -0.0280(6) 0.6684(10) 0.0677(4) 0.069(2) Uani 1 1 d . . .
C22 C -0.0122(4) 0.6565(9) -0.0363(4) 0.0539(18) Uani 1 1 d . . .
C23 C -0.1129(4) 0.6585(9) -0.1203(4) 0.060(2) Uani 1 1 d . . .
H23 H -0.1877 0.6675 -0.1102 0.072 Uiso 1 1 calc R . .
C24 C -0.1060(5) 0.6474(10) -0.2195(4) 0.0619(18) Uani 1 1 d . . .
H24 H -0.1750 0.6456 -0.2759 0.074 Uiso 1 1 calc R . .
C25 C 0.0052(5) 0.6392(10) -0.2331(3) 0.0514(14) Uani 1 1 d . . .
C26 C 0.1059(5) 0.6423(13) -0.1508(4) 0.085(2) Uani 1 1 d . . .
H26 H 0.1810 0.6399 -0.1609 0.102 Uiso 1 1 calc R . .
C27 C 0.0966(5) 0.6490(12) -0.0537(4) 0.077(2) Uani 1 1 d . . .
H27 H 0.1659 0.6484 0.0023 0.092 Uiso 1 1 calc R . .
O1 O 0.6191(3) 0.6465(7) 0.6224(3) 0.0819(15) Uani 1 1 d . . .
O2 O 0.4432(3) 0.6081(7) 0.5141(2) 0.0588(11) Uani 1 1 d . . .
O3 O 0.0745(3) 0.6516(7) 0.1431(2) 0.0691(14) Uani 1 1 d . . .
O4 O -0.1214(4) 0.6883(9) 0.0829(3) 0.115(3) Uani 1 1 d . . .


_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
Br1 C25 1.887(5) . ?
C1 C10 1.521(8) . ?
C1 C2 1.540(9) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.509(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.517(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C18 1.541(8) . ?
C4 C5 1.543(9) . ?
C4 C19 1.548(8) . ?
C5 C6 1.527(8) . ?
C5 C10 1.562(7) . ?
C5 H5 0.9800 . ?
C6 C7 1.494(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.314(7) . ?
C7 H7 0.9300 . ?
C8 C17 1.500(8) . ?
C8 C9 1.502(7) . ?
C9 C11 1.513(7) . ?
C9 C10 1.544(7) . ?
C9 H9 0.9800 . ?
C10 C20 1.529(8) . ?
C11 C12 1.506(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O2 1.469(7) . ?
C12 C13 1.508(8) . ?
C12 H12 0.9800 . ?
C13 C14 1.314(7) . ?
C13 C16 1.492(10) . ?
C14 C15 1.468(7) . ?
C14 H14 0.9300 . ?
C15 O3 1.456(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O1 1.194(6) . ?
C17 O2 1.342(6) . ?
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 O4 1.186(7) . ?
C21 O3 1.328(6) . ?
C21 C22 1.485(7) . ?
C22 C27 1.367(7) . ?
C22 C23 1.371(7) . ?
C23 C24 1.380(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.371(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.358(7) . ?
C26 C27 1.360(7) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?

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
C10 C1 C2 113.4(4) . . ?
C10 C1 H1A 108.9 . . ?
C2 C1 H1A 108.9 . . ?
C10 C1 H1B 108.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C3 C2 C1 110.8(6) . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C2 C3 C4 114.5(6) . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
C4 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 C18 108.0(5) . . ?
C3 C4 C5 108.4(5) . . ?
C18 C4 C5 110.0(5) . . ?
C3 C4 C19 108.4(5) . . ?
C18 C4 C19 107.4(5) . . ?
C5 C4 C19 114.6(5) . . ?
C6 C5 C4 113.1(4) . . ?
C6 C5 C10 111.0(6) . . ?
C4 C5 C10 118.3(4) . . ?
C6 C5 H5 104.2 . . ?
C4 C5 H5 104.2 . . ?
C10 C5 H5 104.2 . . ?
C7 C6 C5 112.6(4) . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C6 123.9(5) . . ?
C8 C7 H7 118.0 . . ?
C6 C7 H7 118.0 . . ?
C7 C8 C17 117.4(5) . . ?
C7 C8 C9 122.3(5) . . ?
C17 C8 C9 120.3(5) . . ?
C8 C9 C11 108.9(5) . . ?
C8 C9 C10 112.5(4) . . ?
C11 C9 C10 116.1(4) . . ?
C8 C9 H9 106.2 . . ?
C11 C9 H9 106.2 . . ?
C10 C9 H9 106.2 . . ?
C1 C10 C20 109.8(5) . . ?
C1 C10 C9 108.5(4) . . ?
C20 C10 C9 110.1(5) . . ?
C1 C10 C5 109.6(5) . . ?
C20 C10 C5 113.4(4) . . ?
C9 C10 C5 105.3(4) . . ?
C12 C11 C9 110.3(4) . . ?
C12 C11 H11A 109.6 . . ?
C9 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C9 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
O2 C12 C11 110.5(4) . . ?
O2 C12 C13 106.3(5) . . ?
C11 C12 C13 114.6(5) . . ?
O2 C12 H12 108.4 . . ?
C11 C12 H12 108.4 . . ?
C13 C12 H12 108.4 . . ?
C14 C13 C16 124.4(6) . . ?
C14 C13 C12 119.2(7) . . ?
C16 C13 C12 116.2(4) . . ?
C13 C14 C15 127.4(6) . . ?
C13 C14 H14 116.3 . . ?
C15 C14 H14 116.3 . . ?
O3 C15 C14 108.2(5) . . ?
O3 C15 H15A 110.1 . . ?
C14 C15 H15A 110.1 . . ?
O3 C15 H15B 110.1 . . ?
C14 C15 H15B 110.1 . . ?
H15A C15 H15B 108.4 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C17 O2 116.9(5) . . ?
O1 C17 C8 124.4(5) . . ?
O2 C17 C8 118.7(5) . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C21 O3 123.2(6) . . ?
O4 C21 C22 124.3(5) . . ?
O3 C21 C22 112.5(5) . . ?
C27 C22 C23 117.9(5) . . ?
C27 C22 C21 124.1(4) . . ?
C23 C22 C21 117.9(5) . . ?
C22 C23 C24 121.5(5) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C25 C24 C23 118.4(4) . . ?
C25 C24 H24 120.8 . . ?
C23 C24 H24 120.8 . . ?
C26 C25 C24 120.8(5) . . ?
C26 C25 Br1 120.6(4) . . ?
C24 C25 Br1 118.5(4) . . ?
C25 C26 C27 119.6(5) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C26 C27 C22 121.7(5) . . ?
C26 C27 H27 119.2 . . ?
C22 C27 H27 119.2 . . ?
C17 O2 C12 122.0(5) . . ?
C21 O3 C15 116.4(4) . . ?

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 -55.9(7) . . . . ?
C1 C2 C3 C4 58.2(8) . . . . ?
C2 C3 C4 C18 -171.4(6) . . . . ?
C2 C3 C4 C5 -52.4(7) . . . . ?
C2 C3 C4 C19 72.6(7) . . . . ?
C3 C4 C5 C6 179.6(5) . . . . ?
C18 C4 C5 C6 -62.6(7) . . . . ?
C19 C4 C5 C6 58.4(7) . . . . ?
C3 C4 C5 C10 47.4(7) . . . . ?
C18 C4 C5 C10 165.2(5) . . . . ?
C19 C4 C5 C10 -73.8(7) . . . . ?
C4 C5 C6 C7 -178.2(5) . . . . ?
C10 C5 C6 C7 -42.5(6) . . . . ?
C5 C6 C7 C8 8.8(9) . . . . ?
C6 C7 C8 C17 -179.5(6) . . . . ?
C6 C7 C8 C9 1.8(9) . . . . ?
C7 C8 C9 C11 152.4(5) . . . . ?
C17 C8 C9 C11 -26.3(7) . . . . ?
C7 C8 C9 C10 22.2(8) . . . . ?
C17 C8 C9 C10 -156.5(5) . . . . ?
C2 C1 C10 C20 -76.4(6) . . . . ?
C2 C1 C10 C9 163.2(5) . . . . ?
C2 C1 C10 C5 48.7(6) . . . . ?
C8 C9 C10 C1 -169.9(5) . . . . ?
C11 C9 C10 C1 63.7(6) . . . . ?
C8 C9 C10 C20 69.9(6) . . . . ?
C11 C9 C10 C20 -56.5(6) . . . . ?
C8 C9 C10 C5 -52.6(6) . . . . ?
C11 C9 C10 C5 -179.0(5) . . . . ?
C6 C5 C10 C1 -179.6(4) . . . . ?
C4 C5 C10 C1 -46.5(6) . . . . ?
C6 C5 C10 C20 -56.6(6) . . . . ?
C4 C5 C10 C20 76.5(7) . . . . ?
C6 C5 C10 C9 63.8(5) . . . . ?
C4 C5 C10 C9 -163.1(5) . . . . ?
C8 C9 C11 C12 55.4(5) . . . . ?
C10 C9 C11 C12 -176.4(4) . . . . ?
C9 C11 C12 O2 -60.1(6) . . . . ?
C9 C11 C12 C13 179.9(5) . . . . ?
O2 C12 C13 C14 132.9(5) . . . . ?
C11 C12 C13 C14 -104.9(6) . . . . ?
O2 C12 C13 C16 -51.7(6) . . . . ?
C11 C12 C13 C16 70.6(7) . . . . ?
C16 C13 C14 C15 -6.9(10) . . . . ?
C12 C13 C14 C15 168.2(6) . . . . ?
C13 C14 C15 O3 137.6(7) . . . . ?
C7 C8 C17 O1 0.7(10) . . . . ?
C9 C8 C17 O1 179.5(5) . . . . ?
C7 C8 C17 O2 -178.4(5) . . . . ?
C9 C8 C17 O2 0.3(8) . . . . ?
O4 C21 C22 C27 173.5(9) . . . . ?
O3 C21 C22 C27 -7.5(11) . . . . ?
O4 C21 C22 C23 -4.3(12) . . . . ?
O3 C21 C22 C23 174.7(7) . . . . ?
C27 C22 C23 C24 2.3(12) . . . . ?
C21 C22 C23 C24 -179.8(7) . . . . ?
C22 C23 C24 C25 -2.0(12) . . . . ?
C23 C24 C25 C26 -0.2(13) . . . . ?
C23 C24 C25 Br1 -179.0(6) . . . . ?
C24 C25 C26 C27 1.9(15) . . . . ?
Br1 C25 C26 C27 -179.3(8) . . . . ?
C25 C26 C27 C22 -1.6(16) . . . . ?
C23 C22 C27 C26 -0.5(14) . . . . ?
C21 C22 C27 C26 -178.3(9) . . . . ?
O1 C17 O2 C12 176.7(5) . . . . ?
C8 C17 O2 C12 -4.1(8) . . . . ?
C11 C12 O2 C17 33.9(7) . . . . ?
C13 C12 O2 C17 158.8(5) . . . . ?
O4 C21 O3 C15 1.5(13) . . . . ?
C22 C21 O3 C15 -177.5(7) . . . . ?
C14 C15 O3 C21 159.4(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.049
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_compound_7
_database_code_depnum_ccdc_archive 'CCDC 1002243'

_audit_creation_date             2014-07-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_shelxl_version_number           2013-2
_chemical_name_common            'crotonlaevin G'
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H36 O5'
_chemical_formula_sum            'C22 H36 O5'
_chemical_formula_weight         380.51
_chemical_absolute_configuration ad
_chemical_optical_rotation       '[\a]^26^~D~=+4.69 (c 0.64, in CHCl3)'
_chemical_melting_point          475.7
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   20.3298(3)
_cell_length_b                   9.17075(12)
_cell_length_c                   24.6190(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.7227(19)
_cell_angle_gamma                90
_cell_volume                     4233.70(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    11542
_cell_measurement_temperature    294.4(2)
_cell_measurement_theta_max      72.5003
_cell_measurement_theta_min      3.5871
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            20139
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.076
_diffrn_reflns_theta_min         3.590
_diffrn_ambient_temperature      294.4(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -28.00   10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000   30.0000 38

#__ type_ start__ end____ width___ exp.time_
  2 omega  -82.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
  3 omega   18.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000   30.0000 45

#__ type_ start__ end____ width___ exp.time_
  4 omega  -23.00    6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 29

#__ type_ start__ end____ width___ exp.time_
  5 omega -118.00  -79.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -99.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
  6 omega  -43.00  -11.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      -58.0000   38.0000  120.0000 32

#__ type_ start__ end____ width___ exp.time_
  7 omega -132.00 -107.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -99.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega -100.00  -74.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      -58.0000 -125.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   43.00  135.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       58.0000 -160.0000 -171.0000 92

#__ type_ start__ end____ width___ exp.time_
 10 omega   27.00  122.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  -90.0000 95

#__ type_ start__ end____ width___ exp.time_
 11 omega -102.00  -60.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  178.0000  -60.0000 42

#__ type_ start__ end____ width___ exp.time_
 12 omega   43.00   68.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   41.00   80.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000    0.0000 39

#__ type_ start__ end____ width___ exp.time_
 14 omega   41.00   75.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000  -90.0000 34

#__ type_ start__ end____ width___ exp.time_
 15 omega  143.00  177.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000 -120.0000 34

#__ type_ start__ end____ width___ exp.time_
 16 omega   41.00   93.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000  120.0000 52

#__ type_ start__ end____ width___ exp.time_
 17 omega  100.00  126.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   42.00  109.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -94.0000  -63.6629 67

#__ type_ start__ end____ width___ exp.time_
 19 omega   66.00   92.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -63.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   51.00   76.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 21 omega   89.00  115.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 22 omega   95.00  178.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000   60.0000 83

#__ type_ start__ end____ width___ exp.time_
 23 omega  127.00  153.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -11.0000  132.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega   73.00  115.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  160.0000   38.0000 42

#__ type_ start__ end____ width___ exp.time_
 25 omega  138.00  164.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  160.0000   38.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   92.00  161.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000   30.0000 69

#__ type_ start__ end____ width___ exp.time_
 27 omega   47.00   85.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000   30.0000 38

#__ type_ start__ end____ width___ exp.time_
 28 omega   46.00  111.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -63.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
 29 omega   54.00   85.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000   30.0000 31

#__ type_ start__ end____ width___ exp.time_
 30 omega   82.00  115.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000  -60.0000 33

#__ type_ start__ end____ width___ exp.time_
 31 omega   46.00   91.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
 32 omega  123.00  154.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -91.0000   90.0000 31

#__ type_ start__ end____ width___ exp.time_
 33 omega   89.00  148.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -77.0000   60.0000 59

#__ type_ start__ end____ width___ exp.time_
 34 omega  108.00  134.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 35 omega   63.00   88.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 36 omega  122.00  148.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 37 omega   63.00   88.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -118.0000  113.0000 25

#__ type_ start__ end____ width___ exp.time_
 38 omega   49.00   75.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 39 omega   78.00  114.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
 40 omega   70.00   95.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 41 omega   87.00  112.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 42 omega  116.00  141.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 43 omega   89.00  114.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -106.0000 -178.8480 25

#__ type_ start__ end____ width___ exp.time_
 44 omega   48.00   80.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -77.0000  -90.0000 32

#__ type_ start__ end____ width___ exp.time_
 45 omega   97.00  123.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 46 omega   47.00   74.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -106.0000 -178.8480 27

#__ type_ start__ end____ width___ exp.time_
 47 omega  -34.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   97.0000  164.0000 27

#__ type_ start__ end____ width___ exp.time_
 48 omega   43.00   68.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 49 omega   43.00   77.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
 50 omega  110.00  136.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000   12.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 51 omega -106.00  -80.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -99.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 52 omega -120.00  -79.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -99.0000   30.0000 41

#__ type_ start__ end____ width___ exp.time_
 53 omega -101.00  -75.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      -58.0000 -125.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 54 omega   92.00  151.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000   90.0000 59

#__ type_ start__ end____ width___ exp.time_
 55 omega   74.00  125.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000  -30.0000 51

#__ type_ start__ end____ width___ exp.time_
 56 omega   60.00   86.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 57 omega   56.00   96.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000   60.0000 40

#__ type_ start__ end____ width___ exp.time_
 58 omega   65.00   97.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -77.0000  120.0000 32

#__ type_ start__ end____ width___ exp.time_
 59 omega   91.00  117.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 60 omega   72.00   98.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000   25.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 61 omega  101.00  127.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000   25.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 62 omega   61.00  104.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -12.0000 -120.0000 43

#__ type_ start__ end____ width___ exp.time_
 63 omega  -31.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000 -120.0000 104

#__ type_ start__ end____ width___ exp.time_
 64 omega  -71.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 95

#__ type_ start__ end____ width___ exp.time_
 65 omega  -82.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -180.0000 48

#__ type_ start__ end____ width___ exp.time_
 66 omega  -71.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   30.0000 95

#__ type_ start__ end____ width___ exp.time_
 67 omega -130.00  -25.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -77.0000  150.0000 105
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0266159000
_diffrn_orient_matrix_UB_12      0.1527482000
_diffrn_orient_matrix_UB_13      0.0078850000
_diffrn_orient_matrix_UB_21      0.0724336000
_diffrn_orient_matrix_UB_22      0.0656336000
_diffrn_orient_matrix_UB_23      0.0064920000
_diffrn_orient_matrix_UB_31      -0.0282641000
_diffrn_orient_matrix_UB_32      0.0242705000
_diffrn_orient_matrix_UB_33      -0.0670481000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.858
_reflns_Friedel_fraction_max     0.855
_reflns_number_gt                7275
_reflns_number_total             7487
_reflns_odcompleteness_completeness 96.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 3043 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     503
_refine_ls_number_reflns         7487
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0743P)²+0.9847P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1181
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 H2BA-O2B
 0.86 with sigma of 0.02
 H2BB-O2B
 0.86 with sigma of 0.02
 H12B-H2BA
 2.2 with sigma of 0.02
 H12-H2B
 2.2 with sigma of 0.03
3. Others
 Fixed Sof: H2A(0.5) H2B(0.5) H5A(0.5) H5B(0.5) H2BA(0.5) H2BB(0.5) H5BB(0.5)
 H5BC(0.5)
4.a Riding coordinates:
 O2(H2A,H2B), O5(H5A,H5B), O5B(H5BB,H5BC)
4.b Ternary CH refined with riding coordinates:
 C5(H5), C9(H9), C12(H12), C5B(H5BA), C9B(H9B), C12B(H12B)
4.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2C,H2D), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,
 H11B), C17(H17A,H17B), C18(H18A,H18B), C1B(H1BA,H1BB), C2B(H2BC,H2BD),
 C3B(H3BA,H3BB), C6B(H6BA,H6BB), C7B(H7BA,H7BB), C11B(H11C,H11D), C17B(H17C,
 H17D), C18B(H18C,H18D)
4.d Aromatic/amide H refined with riding coordinates:
 C14(H14), C14B(H14B)
4.e X=CH2 refined with riding coordinates:
 C15(H15A,H15B), C15B(H15C,H15D)
4.f Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C), C16B(H16D,H16E,H16F), C19B(H19D,H19E,H19F), C20B(H20D,H20E,H20F),
 C22B(H22D,H22E,H22F)
;
_atom_sites_solution_hydrogens   constr
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.46983(9) -0.0692(2) 0.34954(8) 0.0399(4) Uani 1 1 d . . . . .
O2 O 0.50773(11) -0.2955(2) 0.44751(8) 0.0503(5) Uani 1 1 d . . . . .
H2A H 0.4997 -0.2798 0.4795 0.075 Uiso 0.5 1 d R . P A 1
H2B H 0.5177 -0.3828 0.4485 0.075 Uiso 0.5 1 d DR . P A 2
O3 O 0.36775(13) 0.0483(3) 0.24969(9) 0.0605(6) Uani 1 1 d . . . . .
O4 O 0.2912(2) 0.2315(5) 0.22616(18) 0.1226(16) Uani 1 1 d . . . . .
O5 O 0.45014(11) 0.4156(2) 0.52730(11) 0.0597(6) Uani 1 1 d . . . . .
H5A H 0.4678 0.4972 0.5360 0.090 Uiso 0.5 1 d R . P B 1
H5B H 0.4738 0.4172 0.5070 0.090 Uiso 0.5 1 d R . P B 2
C1 C 0.34909(15) -0.0396(3) 0.48784(12) 0.0425(5) Uani 1 1 d . . . . .
H1A H 0.3282 -0.1363 0.4806 0.051 Uiso 1 1 calc R . . . .
H1B H 0.3987 -0.0495 0.5142 0.051 Uiso 1 1 calc R . . . .
C2 C 0.31024(17) 0.0530(3) 0.51806(14) 0.0512(7) Uani 1 1 d . . . . .
H2C H 0.2597 0.0554 0.4936 0.061 Uiso 1 1 calc R . . . .
H2D H 0.3160 0.0086 0.5554 0.061 Uiso 1 1 calc R . . . .
C3 C 0.33903(14) 0.2078(3) 0.52871(13) 0.0468(6) Uani 1 1 d . . . . .
H3A H 0.3879 0.2055 0.5572 0.056 Uiso 1 1 calc R . . . .
H3B H 0.3113 0.2643 0.5456 0.056 Uiso 1 1 calc R . . . .
C4 C 0.33698(13) 0.2845(3) 0.47222(12) 0.0411(5) Uani 1 1 d . . . . .
C5 C 0.37489(11) 0.1854(2) 0.44202(10) 0.0324(4) Uani 1 1 d . . . . .
H5 H 0.4235 0.1743 0.4715 0.039 Uiso 1 1 calc R . . . .
C6 C 0.38438(14) 0.2532(3) 0.38844(12) 0.0427(5) Uani 1 1 d . . . . .
H6A H 0.3384 0.2586 0.3558 0.051 Uiso 1 1 calc R . . . .
H6B H 0.4026 0.3517 0.3980 0.051 Uiso 1 1 calc R . . . .
C7 C 0.43564(14) 0.1638(3) 0.37000(12) 0.0428(5) Uani 1 1 d . . . . .
H7A H 0.4400 0.2089 0.3359 0.051 Uiso 1 1 calc R . . . .
H7B H 0.4824 0.1640 0.4017 0.051 Uiso 1 1 calc R . . . .
C8 C 0.41039(12) 0.0067(3) 0.35515(10) 0.0349(5) Uani 1 1 d . . . . .
C9 C 0.39771(11) -0.0589(2) 0.40812(9) 0.0298(4) Uani 1 1 d . . . . .
H9 H 0.4440 -0.0518 0.4411 0.036 Uiso 1 1 calc R . . . .
C10 C 0.34536(11) 0.0262(2) 0.42895(10) 0.0322(4) Uani 1 1 d . . . . .
C11 C 0.38396(13) -0.2225(2) 0.39856(11) 0.0357(5) Uani 1 1 d . . . . .
H11A H 0.3758 -0.2639 0.4317 0.043 Uiso 1 1 calc R . . . .
H11B H 0.3416 -0.2388 0.3633 0.043 Uiso 1 1 calc R . . . .
C12 C 0.44754(13) -0.2972(3) 0.39233(10) 0.0367(5) Uani 1 1 d . . . . .
H12 H 0.4347 -0.3991 0.3812 0.044 Uiso 1 1 calc DR . . . .
C13 C 0.46791(13) -0.2262(3) 0.34462(11) 0.0391(5) Uani 1 1 d . . . . .
C14 C 0.41967(16) -0.2754(4) 0.28329(11) 0.0519(7) Uani 1 1 d . . . . .
H14 H 0.4121 -0.2078 0.2533 0.062 Uiso 1 1 calc R . . . .
C15 C 0.3873(2) -0.4014(5) 0.26721(17) 0.0834(12) Uani 1 1 d . . . . .
H15A H 0.3927 -0.4735 0.2952 0.100 Uiso 1 1 calc R . . . .
H15B H 0.3588 -0.4185 0.2278 0.100 Uiso 1 1 calc R . . . .
C16 C 0.54413(15) -0.2647(4) 0.35257(14) 0.0545(7) Uani 1 1 d . . . . .
H16A H 0.5545 -0.2231 0.3210 0.082 Uiso 1 1 calc GR . . . .
H16B H 0.5491 -0.3688 0.3523 0.082 Uiso 1 1 calc GR . . . .
H16C H 0.5768 -0.2265 0.3894 0.082 Uiso 1 1 calc GR . . . .
C17 C 0.34520(14) 0.0016(3) 0.29625(11) 0.0454(6) Uani 1 1 d . . . . .
H17A H 0.3263 -0.0967 0.2886 0.055 Uiso 1 1 calc R . . . .
H17B H 0.3081 0.0658 0.2979 0.055 Uiso 1 1 calc R . . . .
C18 C 0.37689(15) 0.4302(3) 0.49057(15) 0.0513(7) Uani 1 1 d . . . . .
H18A H 0.3730 0.4831 0.4553 0.062 Uiso 1 1 calc R . . . .
H18B H 0.3537 0.4880 0.5111 0.062 Uiso 1 1 calc R . . . .
C19 C 0.26032(14) 0.3284(4) 0.43303(17) 0.0598(8) Uani 1 1 d . . . . .
H19A H 0.2594 0.3670 0.3965 0.090 Uiso 1 1 calc GR . . . .
H19B H 0.2438 0.4011 0.4528 0.090 Uiso 1 1 calc GR . . . .
H19C H 0.2299 0.2443 0.4253 0.090 Uiso 1 1 calc GR . . . .
C20 C 0.26760(12) 0.0148(3) 0.38330(13) 0.0456(6) Uani 1 1 d . . . . .
H20A H 0.2584 0.0924 0.3551 0.068 Uiso 1 1 calc GR . . . .
H20B H 0.2353 0.0223 0.4031 0.068 Uiso 1 1 calc GR . . . .
H20C H 0.2609 -0.0773 0.3634 0.068 Uiso 1 1 calc GR . . . .
C21 C 0.33594(19) 0.1599(4) 0.21732(14) 0.0624(8) Uani 1 1 d . . . . .
C22 C 0.3674(3) 0.1993(5) 0.17364(18) 0.0849(13) Uani 1 1 d . . . . .
H22A H 0.4083 0.1392 0.1798 0.127 Uiso 1 1 calc GR . . . .
H22B H 0.3815 0.2999 0.1785 0.127 Uiso 1 1 calc GR . . . .
H22C H 0.3325 0.1843 0.1345 0.127 Uiso 1 1 calc GR . . . .
O1B O 0.19227(8) 0.47497(18) 0.55904(7) 0.0353(3) Uani 1 1 d . . . . .
O2B O 0.07087(9) 0.6928(2) 0.50676(8) 0.0450(4) Uani 1 1 d D . . . .
H2BA H 0.057(3) 0.775(4) 0.4875(14) 0.053(18) Uiso 0.5 1 d D . P C 2
H2BB H 0.035(2) 0.689(9) 0.517(3) 0.06(2) Uiso 0.5 1 d D . P D 2
O3B O 0.29743(10) 0.3601(3) 0.65996(9) 0.0568(5) Uani 1 1 d . . . . .
O4B O 0.3226(3) 0.2295(7) 0.7391(2) 0.174(3) Uani 1 1 d . . . . .
C1B C -0.01597(13) 0.4337(3) 0.61303(12) 0.0394(5) Uani 1 1 d . . . . .
H1BA H -0.0128 0.5313 0.6290 0.047 Uiso 1 1 calc R . . . .
H1BB H -0.0381 0.4411 0.5705 0.047 Uiso 1 1 calc R . . . .
C2B C -0.06306(14) 0.3408(3) 0.63471(13) 0.0459(6) Uani 1 1 d . . . . .
H2BC H -0.0437 0.3413 0.6774 0.055 Uiso 1 1 calc R . . . .
H2BD H -0.1105 0.3827 0.6209 0.055 Uiso 1 1 calc R . . . .
C3B C -0.06783(14) 0.1842(3) 0.61287(13) 0.0451(6) Uani 1 1 d . . . . .
H3BA H -0.0938 0.1833 0.5705 0.054 Uiso 1 1 calc R . . . .
H3BB H -0.0950 0.1273 0.6302 0.054 Uiso 1 1 calc R . . . .
C4B C 0.00498(14) 0.1109(3) 0.62746(11) 0.0391(5) Uani 1 1 d . . . . .
C5B C 0.05196(12) 0.2119(2) 0.60641(9) 0.0327(4) Uani 1 1 d . . . . .
H5BA H 0.0253 0.2219 0.5639 0.039 Uiso 1 1 calc R . . . .
C6B C 0.12442(14) 0.1475(3) 0.61247(12) 0.0403(5) Uani 1 1 d . . . . .
H6BA H 0.1555 0.1425 0.6538 0.048 Uiso 1 1 calc R . . . .
H6BB H 0.1174 0.0491 0.5969 0.048 Uiso 1 1 calc R . . . .
C7B C 0.16019(13) 0.2398(3) 0.57954(12) 0.0391(5) Uani 1 1 d . . . . .
H7BA H 0.2059 0.1971 0.5850 0.047 Uiso 1 1 calc R . . . .
H7BB H 0.1307 0.2386 0.5378 0.047 Uiso 1 1 calc R . . . .
C8B C 0.17140(12) 0.3973(2) 0.60116(10) 0.0325(4) Uani 1 1 d . . . . .
C9B C 0.09897(11) 0.4585(2) 0.59729(9) 0.0285(4) Uani 1 1 d . . . . .
H9B H 0.0677 0.4496 0.5556 0.034 Uiso 1 1 calc R . . . .
C10B C 0.06007(12) 0.3715(2) 0.63063(9) 0.0312(4) Uani 1 1 d . . . . .
C11B C 0.10509(13) 0.6230(2) 0.60906(10) 0.0340(5) Uani 1 1 d . . . . .
H11C H 0.0595 0.6611 0.6067 0.041 Uiso 1 1 calc R . . . .
H11D H 0.1401 0.6417 0.6484 0.041 Uiso 1 1 calc R . . . .
C12B C 0.12740(12) 0.6991(2) 0.56388(10) 0.0343(5) Uani 1 1 d . . . . .
H12B H 0.1369 0.8018 0.5752 0.041 Uiso 1 1 calc DR . . . .
C13B C 0.19560(12) 0.6323(3) 0.56128(11) 0.0351(5) Uani 1 1 d . . . . .
C14B C 0.26227(13) 0.6852(3) 0.61131(13) 0.0478(6) Uani 1 1 d . . . . .
H14B H 0.3018 0.6243 0.6212 0.057 Uiso 1 1 calc R . . . .
C15B C 0.27192(19) 0.8044(5) 0.64246(18) 0.0730(10) Uani 1 1 d . . . . .
H15C H 0.2346 0.8703 0.6349 0.088 Uiso 1 1 calc R . . . .
H15D H 0.3161 0.8235 0.6722 0.088 Uiso 1 1 calc R . . . .
C16B C 0.20309(15) 0.6746(3) 0.50378(12) 0.0469(6) Uani 1 1 d . . . . .
H16D H 0.2489 0.6442 0.5053 0.070 Uiso 1 1 calc GR . . . .
H16E H 0.1987 0.7784 0.4987 0.070 Uiso 1 1 calc GR . . . .
H16F H 0.1663 0.6276 0.4713 0.070 Uiso 1 1 calc GR . . . .
C17B C 0.23065(13) 0.4056(3) 0.66299(11) 0.0430(5) Uani 1 1 d . . . . .
H17C H 0.2349 0.5047 0.6777 0.052 Uiso 1 1 calc R . . . .
H17D H 0.2191 0.3426 0.6897 0.052 Uiso 1 1 calc R . . . .
C18B C -0.00890(17) -0.0350(3) 0.59378(14) 0.0505(6) Uani 1 1 d . . . . .
H18C H 0.0363 -0.0844 0.6028 0.061 Uiso 1 1 calc R . . . .
H18D H -0.0381 -0.0961 0.6077 0.061 Uiso 1 1 calc R . . . .
C19B C 0.03903(19) 0.0659(4) 0.69274(13) 0.0562(7) Uani 1 1 d . . . . .
H19D H 0.0870 0.0334 0.7019 0.084 Uiso 1 1 calc GR . . . .
H19E H 0.0118 -0.0117 0.7000 0.084 Uiso 1 1 calc GR . . . .
H19F H 0.0395 0.1481 0.7171 0.084 Uiso 1 1 calc GR . . . .
C20B C 0.09929(15) 0.3857(3) 0.69809(10) 0.0432(5) Uani 1 1 d . . . . .
H20D H 0.1343 0.3097 0.7123 0.065 Uiso 1 1 calc GR . . . .
H20E H 0.0655 0.3773 0.7165 0.065 Uiso 1 1 calc GR . . . .
H20F H 0.1225 0.4789 0.7074 0.065 Uiso 1 1 calc GR . . . .
C21B C 0.33753(18) 0.2699(5) 0.70079(15) 0.0675(9) Uani 1 1 d . . . . .
C22B C 0.4054(2) 0.2333(7) 0.69360(19) 0.0928(16) Uani 1 1 d . . . . .
H22D H 0.4012 0.1387 0.6759 0.139 Uiso 1 1 calc GR . . . .
H22E H 0.4441 0.2329 0.7315 0.139 Uiso 1 1 calc GR . . . .
H22F H 0.4144 0.3048 0.6688 0.139 Uiso 1 1 calc GR . . . .
O5B O -0.04321(13) -0.0201(2) 0.53189(10) 0.0619(6) Uani 1 1 d . . . . .
H5BB H -0.0133 -0.0133 0.5173 0.093 Uiso 0.5 1 d R . P E 1
H5BC H -0.0583 -0.1069 0.5193 0.093 Uiso 0.5 1 d R . P E 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.447(3) . ?
O1 C13 1.444(3) . ?
O2 H2A 0.8750 . ?
O2 H2B 0.8242 . ?
O2 C12 1.435(3) . ?
O3 C17 1.454(3) . ?
O3 C21 1.305(4) . ?
O4 C21 1.208(5) . ?
O5 H5A 0.8215 . ?
O5 H5B 0.8158 . ?
O5 C18 1.419(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.534(3) . ?
C1 C10 1.545(3) . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C2 C3 1.519(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.545(4) . ?
C4 C5 1.554(3) . ?
C4 C18 1.538(3) . ?
C4 C19 1.536(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.536(3) . ?
C5 C10 1.564(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.526(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.526(3) . ?
C8 C9 1.546(3) . ?
C8 C17 1.542(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.558(3) . ?
C9 C11 1.527(3) . ?
C10 C20 1.549(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.522(3) . ?
C12 H12 0.9800 . ?
C12 C13 1.533(3) . ?
C13 C14 1.517(3) . ?
C13 C16 1.526(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.313(6) . ?
C15 H15A 0.9300 . ?
C15 H15B 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
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 1.492(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O1B C8B 1.450(3) . ?
O1B C13B 1.444(3) . ?
O2B H2BA 0.87(3) . ?
O2B H2BB 0.85(3) . ?
O2B C12B 1.433(3) . ?
O3B C17B 1.450(3) . ?
O3B C21B 1.314(4) . ?
O4B C21B 1.158(5) . ?
C1B H1BA 0.9700 . ?
C1B H1BB 0.9700 . ?
C1B C2B 1.524(3) . ?
C1B C10B 1.545(3) . ?
C2B H2BC 0.9700 . ?
C2B H2BD 0.9700 . ?
C2B C3B 1.523(4) . ?
C3B H3BA 0.9700 . ?
C3B H3BB 0.9700 . ?
C3B C4B 1.537(4) . ?
C4B C5B 1.556(3) . ?
C4B C18B 1.541(3) . ?
C4B C19B 1.540(4) . ?
C5B H5BA 0.9800 . ?
C5B C6B 1.540(3) . ?
C5B C10B 1.564(3) . ?
C6B H6BA 0.9700 . ?
C6B H6BB 0.9700 . ?
C6B C7B 1.536(3) . ?
C7B H7BA 0.9700 . ?
C7B H7BB 0.9700 . ?
C7B C8B 1.525(3) . ?
C8B C9B 1.544(3) . ?
C8B C17B 1.535(3) . ?
C9B H9B 0.9800 . ?
C9B C10B 1.562(3) . ?
C9B C11B 1.532(3) . ?
C10B C20B 1.545(3) . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?
C11B C12B 1.523(3) . ?
C12B H12B 0.9800 . ?
C12B C13B 1.540(3) . ?
C13B C14B 1.517(3) . ?
C13B C16B 1.531(3) . ?
C14B H14B 0.9300 . ?
C14B C15B 1.306(5) . ?
C15B H15C 0.9300 . ?
C15B H15D 0.9300 . ?
C16B H16D 0.9600 . ?
C16B H16E 0.9600 . ?
C16B H16F 0.9600 . ?
C17B H17C 0.9700 . ?
C17B H17D 0.9700 . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
C18B O5B 1.416(4) . ?
C19B H19D 0.9600 . ?
C19B H19E 0.9600 . ?
C19B H19F 0.9600 . ?
C20B H20D 0.9600 . ?
C20B H20E 0.9600 . ?
C20B H20F 0.9600 . ?
C21B C22B 1.495(5) . ?
C22B H22D 0.9600 . ?
C22B H22E 0.9600 . ?
C22B H22F 0.9600 . ?
O5B H5BB 0.8199 . ?
O5B H5BC 0.8666 . ?

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
C13 O1 C8 119.42(19) . . ?
C12 O2 H2A 117.8 . . ?
C12 O2 H2B 97.3 . . ?
C21 O3 C17 118.7(2) . . ?
C18 O5 H5A 109.0 . . ?
C18 O5 H5B 109.3 . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
C2 C1 C10 113.0(2) . . ?
C10 C1 H1A 109.0 . . ?
C10 C1 H1B 109.0 . . ?
C1 C2 H2C 109.4 . . ?
C1 C2 H2D 109.4 . . ?
H2C C2 H2D 108.0 . . ?
C3 C2 C1 111.4(2) . . ?
C3 C2 H2C 109.4 . . ?
C3 C2 H2D 109.4 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C2 C3 C4 113.3(2) . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C3 C4 C5 108.6(2) . . ?
C18 C4 C3 107.7(2) . . ?
C18 C4 C5 110.2(2) . . ?
C19 C4 C3 110.6(2) . . ?
C19 C4 C5 115.0(2) . . ?
C19 C4 C18 104.4(2) . . ?
C4 C5 H5 104.6 . . ?
C4 C5 C10 114.99(18) . . ?
C6 C5 C4 115.1(2) . . ?
C6 C5 H5 104.6 . . ?
C6 C5 C10 111.48(19) . . ?
C10 C5 H5 104.6 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 C5 111.4(2) . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 C6 111.9(2) . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
O1 C8 C7 105.13(19) . . ?
O1 C8 C9 108.11(17) . . ?
O1 C8 C17 110.0(2) . . ?
C7 C8 C9 108.40(19) . . ?
C7 C8 C17 109.9(2) . . ?
C17 C8 C9 114.78(19) . . ?
C8 C9 H9 104.7 . . ?
C8 C9 C10 116.12(18) . . ?
C10 C9 H9 104.7 . . ?
C11 C9 C8 109.43(19) . . ?
C11 C9 H9 104.7 . . ?
C11 C9 C10 115.82(18) . . ?
C1 C10 C5 107.20(19) . . ?
C1 C10 C9 108.71(18) . . ?
C1 C10 C20 108.7(2) . . ?
C9 C10 C5 106.22(17) . . ?
C20 C10 C5 114.5(2) . . ?
C20 C10 C9 111.26(19) . . ?
C9 C11 H11A 109.6 . . ?
C9 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 C9 110.23(19) . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
O2 C12 C11 110.27(19) . . ?
O2 C12 H12 108.2 . . ?
O2 C12 C13 109.7(2) . . ?
C11 C12 H12 108.2 . . ?
C11 C12 C13 112.14(19) . . ?
C13 C12 H12 108.2 . . ?
O1 C13 C12 111.46(19) . . ?
O1 C13 C14 111.5(2) . . ?
O1 C13 C16 103.1(2) . . ?
C14 C13 C12 112.0(2) . . ?
C14 C13 C16 107.0(2) . . ?
C16 C13 C12 111.4(2) . . ?
C13 C14 H14 115.9 . . ?
C15 C14 C13 128.2(3) . . ?
C15 C14 H14 115.9 . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 C8 108.3(2) . . ?
O3 C17 H17A 110.0 . . ?
O3 C17 H17B 110.0 . . ?
C8 C17 H17A 110.0 . . ?
C8 C17 H17B 110.0 . . ?
H17A C17 H17B 108.4 . . ?
O5 C18 C4 114.2(2) . . ?
O5 C18 H18A 108.7 . . ?
O5 C18 H18B 108.7 . . ?
C4 C18 H18A 108.7 . . ?
C4 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 C22 112.4(3) . . ?
O4 C21 O3 123.1(3) . . ?
O4 C21 C22 124.0(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C13B O1B C8B 119.07(18) . . ?
H2BA O2B H2BB 94(6) . . ?
C12B O2B H2BA 118(2) . . ?
C12B O2B H2BB 99(5) . . ?
C21B O3B C17B 117.3(2) . . ?
H1BA C1B H1BB 107.8 . . ?
C2B C1B H1BA 109.0 . . ?
C2B C1B H1BB 109.0 . . ?
C2B C1B C10B 113.0(2) . . ?
C10B C1B H1BA 109.0 . . ?
C10B C1B H1BB 109.0 . . ?
C1B C2B H2BC 109.3 . . ?
C1B C2B H2BD 109.3 . . ?
H2BC C2B H2BD 108.0 . . ?
C3B C2B C1B 111.5(2) . . ?
C3B C2B H2BC 109.3 . . ?
C3B C2B H2BD 109.3 . . ?
C2B C3B H3BA 108.8 . . ?
C2B C3B H3BB 108.8 . . ?
C2B C3B C4B 113.9(2) . . ?
H3BA C3B H3BB 107.7 . . ?
C4B C3B H3BA 108.8 . . ?
C4B C3B H3BB 108.8 . . ?
C3B C4B C5B 108.7(2) . . ?
C3B C4B C18B 107.1(2) . . ?
C3B C4B C19B 111.4(2) . . ?
C18B C4B C5B 110.2(2) . . ?
C19B C4B C5B 114.9(2) . . ?
C19B C4B C18B 104.1(2) . . ?
C4B C5B H5BA 104.7 . . ?
C4B C5B C10B 114.69(18) . . ?
C6B C5B C4B 115.3(2) . . ?
C6B C5B H5BA 104.7 . . ?
C6B C5B C10B 111.46(19) . . ?
C10B C5B H5BA 104.7 . . ?
C5B C6B H6BA 109.3 . . ?
C5B C6B H6BB 109.3 . . ?
H6BA C6B H6BB 108.0 . . ?
C7B C6B C5B 111.58(19) . . ?
C7B C6B H6BA 109.3 . . ?
C7B C6B H6BB 109.3 . . ?
C6B C7B H7BA 109.2 . . ?
C6B C7B H7BB 109.2 . . ?
H7BA C7B H7BB 107.9 . . ?
C8B C7B C6B 112.03(19) . . ?
C8B C7B H7BA 109.2 . . ?
C8B C7B H7BB 109.2 . . ?
O1B C8B C7B 105.13(18) . . ?
O1B C8B C9B 108.21(17) . . ?
O1B C8B C17B 110.51(19) . . ?
C7B C8B C9B 108.20(18) . . ?
C7B C8B C17B 110.3(2) . . ?
C17B C8B C9B 114.04(18) . . ?
C8B C9B H9B 104.6 . . ?
C8B C9B C10B 116.50(17) . . ?
C10B C9B H9B 104.6 . . ?
C11B C9B C8B 109.91(18) . . ?
C11B C9B H9B 104.6 . . ?
C11B C9B C10B 115.12(17) . . ?
C1B C10B C5B 106.98(18) . . ?
C1B C10B C9B 108.59(18) . . ?
C1B C10B C20B 108.38(19) . . ?
C9B C10B C5B 106.14(16) . . ?
C20B C10B C5B 115.04(19) . . ?
C20B C10B C9B 111.47(18) . . ?
C9B C11B H11C 109.7 . . ?
C9B C11B H11D 109.7 . . ?
H11C C11B H11D 108.2 . . ?
C12B C11B C9B 109.77(18) . . ?
C12B C11B H11C 109.7 . . ?
C12B C11B H11D 109.7 . . ?
O2B C12B C11B 110.25(18) . . ?
O2B C12B H12B 108.2 . . ?
O2B C12B C13B 109.70(19) . . ?
C11B C12B H12B 108.2 . . ?
C11B C12B C13B 112.04(19) . . ?
C13B C12B H12B 108.2 . . ?
O1B C13B C12B 111.67(18) . . ?
O1B C13B C14B 111.4(2) . . ?
O1B C13B C16B 103.75(19) . . ?
C14B C13B C12B 112.1(2) . . ?
C14B C13B C16B 107.0(2) . . ?
C16B C13B C12B 110.5(2) . . ?
C13B C14B H14B 115.5 . . ?
C15B C14B C13B 129.0(3) . . ?
C15B C14B H14B 115.5 . . ?
C14B C15B H15C 120.0 . . ?
C14B C15B H15D 120.0 . . ?
H15C C15B H15D 120.0 . . ?
C13B C16B H16D 109.5 . . ?
C13B C16B H16E 109.5 . . ?
C13B C16B H16F 109.5 . . ?
H16D C16B H16E 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
O3B C17B C8B 109.0(2) . . ?
O3B C17B H17C 109.9 . . ?
O3B C17B H17D 109.9 . . ?
C8B C17B H17C 109.9 . . ?
C8B C17B H17D 109.9 . . ?
H17C C17B H17D 108.3 . . ?
C4B C18B H18C 108.8 . . ?
C4B C18B H18D 108.8 . . ?
H18C C18B H18D 107.6 . . ?
O5B C18B C4B 114.0(2) . . ?
O5B C18B H18C 108.8 . . ?
O5B C18B H18D 108.8 . . ?
C4B C19B H19D 109.5 . . ?
C4B C19B H19E 109.5 . . ?
C4B C19B H19F 109.5 . . ?
H19D C19B H19E 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
C10B C20B H20D 109.5 . . ?
C10B C20B H20E 109.5 . . ?
C10B C20B H20F 109.5 . . ?
H20D C20B H20E 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
O3B C21B C22B 112.3(3) . . ?
O4B C21B O3B 123.0(3) . . ?
O4B C21B C22B 124.7(4) . . ?
C21B C22B H22D 109.5 . . ?
C21B C22B H22E 109.5 . . ?
C21B C22B H22F 109.5 . . ?
H22D C22B H22E 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
C18B O5B H5BB 109.8 . . ?
C18B O5B H5BC 104.8 . . ?

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
O1 C8 C9 C10 169.02(18) . . . . ?
O1 C8 C9 C11 -57.6(2) . . . . ?
O1 C8 C17 O3 -50.2(3) . . . . ?
O1 C13 C14 C15 -156.4(4) . . . . ?
O2 C12 C13 O1 -76.9(2) . . . . ?
O2 C12 C13 C14 157.5(2) . . . . ?
O2 C12 C13 C16 37.7(3) . . . . ?
C1 C2 C3 C4 55.1(3) . . . . ?
C2 C1 C10 C5 55.0(3) . . . . ?
C2 C1 C10 C9 169.5(2) . . . . ?
C2 C1 C10 C20 -69.3(3) . . . . ?
C2 C3 C4 C5 -52.9(3) . . . . ?
C2 C3 C4 C18 -172.2(2) . . . . ?
C2 C3 C4 C19 74.3(3) . . . . ?
C3 C4 C5 C6 -173.9(2) . . . . ?
C3 C4 C5 C10 54.4(2) . . . . ?
C3 C4 C18 O5 62.7(3) . . . . ?
C4 C5 C6 C7 167.6(2) . . . . ?
C4 C5 C10 C1 -55.4(2) . . . . ?
C4 C5 C10 C9 -171.48(19) . . . . ?
C4 C5 C10 C20 65.3(3) . . . . ?
C5 C4 C18 O5 -55.5(3) . . . . ?
C5 C6 C7 C8 58.3(3) . . . . ?
C6 C5 C10 C1 171.25(19) . . . . ?
C6 C5 C10 C9 55.2(2) . . . . ?
C6 C5 C10 C20 -68.1(3) . . . . ?
C6 C7 C8 O1 -169.60(19) . . . . ?
C6 C7 C8 C9 -54.2(3) . . . . ?
C6 C7 C8 C17 72.0(3) . . . . ?
C7 C8 C9 C10 55.5(2) . . . . ?
C7 C8 C9 C11 -171.05(19) . . . . ?
C7 C8 C17 O3 65.1(3) . . . . ?
C8 O1 C13 C12 -49.1(3) . . . . ?
C8 O1 C13 C14 76.8(3) . . . . ?
C8 O1 C13 C16 -168.67(19) . . . . ?
C8 C9 C10 C1 -170.56(19) . . . . ?
C8 C9 C10 C5 -55.5(2) . . . . ?
C8 C9 C10 C20 69.8(3) . . . . ?
C8 C9 C11 C12 59.5(2) . . . . ?
C9 C8 C17 O3 -172.4(2) . . . . ?
C9 C11 C12 O2 69.0(3) . . . . ?
C9 C11 C12 C13 -53.5(3) . . . . ?
C10 C1 C2 C3 -56.8(3) . . . . ?
C10 C5 C6 C7 -59.1(3) . . . . ?
C10 C9 C11 C12 -166.96(18) . . . . ?
C11 C9 C10 C1 59.0(2) . . . . ?
C11 C9 C10 C5 174.06(19) . . . . ?
C11 C9 C10 C20 -60.7(3) . . . . ?
C11 C12 C13 O1 46.0(3) . . . . ?
C11 C12 C13 C14 -79.6(3) . . . . ?
C11 C12 C13 C16 160.5(2) . . . . ?
C12 C13 C14 C15 -30.8(4) . . . . ?
C13 O1 C8 C7 170.4(2) . . . . ?
C13 O1 C8 C9 54.7(3) . . . . ?
C13 O1 C8 C17 -71.3(3) . . . . ?
C16 C13 C14 C15 91.6(4) . . . . ?
C17 O3 C21 O4 4.2(6) . . . . ?
C17 O3 C21 C22 177.0(3) . . . . ?
C17 C8 C9 C10 -67.8(3) . . . . ?
C17 C8 C9 C11 65.6(3) . . . . ?
C18 C4 C5 C6 -56.2(3) . . . . ?
C18 C4 C5 C10 172.2(2) . . . . ?
C19 C4 C5 C6 61.5(3) . . . . ?
C19 C4 C5 C10 -70.1(3) . . . . ?
C19 C4 C18 O5 -179.6(3) . . . . ?
C21 O3 C17 C8 -122.2(3) . . . . ?
O1B C8B C9B C10B 169.24(17) . . . . ?
O1B C8B C9B C11B -57.5(2) . . . . ?
O1B C8B C17B O3B -51.8(3) . . . . ?
O1B C13B C14B C15B -149.5(3) . . . . ?
O2B C12B C13B O1B -76.1(2) . . . . ?
O2B C12B C13B C14B 158.1(2) . . . . ?
O2B C12B C13B C16B 38.8(3) . . . . ?
C1B C2B C3B C4B 53.9(3) . . . . ?
C2B C1B C10B C5B 56.1(3) . . . . ?
C2B C1B C10B C9B 170.2(2) . . . . ?
C2B C1B C10B C20B -68.5(3) . . . . ?
C2B C3B C4B C5B -51.6(3) . . . . ?
C2B C3B C4B C18B -170.7(2) . . . . ?
C2B C3B C4B C19B 76.0(3) . . . . ?
C3B C4B C5B C6B -174.4(2) . . . . ?
C3B C4B C5B C10B 54.1(3) . . . . ?
C3B C4B C18B O5B 59.5(3) . . . . ?
C4B C5B C6B C7B 168.4(2) . . . . ?
C4B C5B C10B C1B -56.1(2) . . . . ?
C4B C5B C10B C9B -171.89(18) . . . . ?
C4B C5B C10B C20B 64.4(3) . . . . ?
C5B C4B C18B O5B -58.6(3) . . . . ?
C5B C6B C7B C8B 57.8(3) . . . . ?
C6B C5B C10B C1B 170.68(19) . . . . ?
C6B C5B C10B C9B 54.9(2) . . . . ?
C6B C5B C10B C20B -68.9(2) . . . . ?
C6B C7B C8B O1B -169.35(19) . . . . ?
C6B C7B C8B C9B -53.9(2) . . . . ?
C6B C7B C8B C17B 71.5(3) . . . . ?
C7B C8B C9B C10B 55.8(2) . . . . ?
C7B C8B C9B C11B -170.93(18) . . . . ?
C7B C8B C17B O3B 64.1(3) . . . . ?
C8B O1B C13B C12B -49.2(3) . . . . ?
C8B O1B C13B C14B 76.9(3) . . . . ?
C8B O1B C13B C16B -168.26(18) . . . . ?
C8B C9B C10B C1B -170.53(19) . . . . ?
C8B C9B C10B C5B -55.8(2) . . . . ?
C8B C9B C10B C20B 70.1(2) . . . . ?
C8B C9B C11B C12B 59.5(2) . . . . ?
C9B C8B C17B O3B -173.9(2) . . . . ?
C9B C11B C12B O2B 68.9(2) . . . . ?
C9B C11B C12B C13B -53.6(3) . . . . ?
C10B C1B C2B C3B -56.5(3) . . . . ?
C10B C5B C6B C7B -58.6(3) . . . . ?
C10B C9B C11B C12B -166.58(18) . . . . ?
C11B C9B C10B C1B 58.6(2) . . . . ?
C11B C9B C10B C5B 173.33(18) . . . . ?
C11B C9B C10B C20B -60.7(2) . . . . ?
C11B C12B C13B O1B 46.7(3) . . . . ?
C11B C12B C13B C14B -79.1(3) . . . . ?
C11B C12B C13B C16B 161.6(2) . . . . ?
C12B C13B C14B C15B -23.6(4) . . . . ?
C13B O1B C8B C7B 169.85(19) . . . . ?
C13B O1B C8B C9B 54.4(3) . . . . ?
C13B O1B C8B C17B -71.1(2) . . . . ?
C16B C13B C14B C15B 97.8(4) . . . . ?
C17B O3B C21B O4B -2.1(7) . . . . ?
C17B O3B C21B C22B -178.9(3) . . . . ?
C17B C8B C9B C10B -67.4(3) . . . . ?
C17B C8B C9B C11B 65.9(2) . . . . ?
C18B C4B C5B C6B -57.3(3) . . . . ?
C18B C4B C5B C10B 171.3(2) . . . . ?
C19B C4B C5B C6B 60.0(3) . . . . ?
C19B C4B C5B C10B -71.5(3) . . . . ?
C19B C4B C18B O5B 177.6(2) . . . . ?
C21B O3B C17B C8B -135.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_compound_8
_database_code_depnum_ccdc_archive 'CCDC 1002244'
_audit_creation_date             2014-07-28
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H36 O5,0.5(C H2 Cl2)'
_chemical_formula_sum            'C22.50 H37 Cl O5'
_chemical_formula_weight         422.97
_chemical_absolute_configuration unk
_chemical_melting_point          415.7
_chemical_optical_rotation       '[\a]^26^~D~=+9.09 (c 0.11, in CHCl3)'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   26.328(15)
_cell_length_b                   11.042(7)
_cell_length_c                   19.217(19)
_cell_angle_alpha                90
_cell_angle_beta                 129.100(4)
_cell_angle_gamma                90
_cell_volume                     4336(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2123
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.47
_cell_measurement_theta_min      2.73
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.954
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1832
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.1320
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14626
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         2.131
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_full    0.951
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                4290
_reflns_number_total             7875
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1256 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.30(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     538
_refine_ls_number_reflns         7875
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1511
_refine_ls_R_factor_gt           0.0782
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1362
_refine_special_details          
;
 DCM molecule of crystallisation is located on a twofold axis and intensely 
disordered. The disorder was modelled by Cl(1)C(45)H₂Cl(1') position with 
occupancy 50% and three independent Cl positions, Cl(2), Cl(3) & Cl(4), for 
which no methylene positions could be refined satisfactorily. Atoms C(45) and 
Cl(2) are located on the twofold axis. 
  Vinyl group C(36)H\db C(37)H₂ is rotationally disordered between positions 
A and B with occupancies 83% and 17%, respectively.  
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C37-C36A \\sim C36B-C37B
 with sigma of 0.02
 C36A-C35 \\sim C36B-C35
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uiso(C36A) = Uiso(C36B)
4. Others
 Fixed Sof: C36A(0.83) H36A(0.83) C37(0.83) H37A(0.83) H37B(0.83) C36B(0.17)
 H36B(0.17) C37B(0.17) H37C(0.17) H37D(0.17) Cl1(0.5) C45(0.25) H45(0.5)
 Cl2(0.125) Cl3(0.25) Cl4(0.125)
5.a Riding coordinates:
 C45(H45)
5.b Ternary CH refined with riding coordinates:
 C27(H27), C31(H31), C34(H34), C5(H5), C9(H9), C12(H12)
5.c Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C28(H28A,H28B), C29(H29A,
 H29B), C33(H33A,H33B), C39(H39A,H39B), C40(H40A,H40B), C1(H1A,H1B), C2(H2A,
 H2B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C17(H17A,H17B),
 C18(H18A,H18B)
5.d Aromatic/amide H refined with riding coordinates:
 C36A(H36A), C36B(H36B), C14(H14)
5.e X=CH2 refined with riding coordinates:
 C37(H37A,H37B), C37B(H37C,H37D), C15(H15A,H15B)
5.f Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C44(H44A,H44B,
 H44C), C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,
 H22B,H22C)
5.g Idealised tetrahedral OH refined as rotating group:
 O6(H6), O7(H7), O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O6 O 0.1981(3) 0.9616(4) 0.2185(3) 0.0608(14) Uani 1 1 d . . . . .
H6 H 0.1919 1.0033 0.2477 0.091 Uiso 1 1 calc GR . . . .
O7 O 0.2088(2) 0.0937(4) 0.3476(4) 0.0530(13) Uani 1 1 d . . . . .
H7 H 0.1736 0.0915 0.3376 0.079 Uiso 1 1 calc GR . . . .
O8 O 0.3328(2) 0.3300(4) 0.4375(3) 0.0420(11) Uani 1 1 d . . . . .
O9 O 0.3957(2) 0.3251(4) 0.3625(3) 0.0465(12) Uani 1 1 d . . . . .
O10 O 0.4032(3) 0.4436(6) 0.2761(4) 0.0791(19) Uani 1 1 d . . . . .
C23 C 0.1256(3) 0.5190(6) 0.1903(4) 0.0471(19) Uani 1 1 d . . . . .
H23A H 0.1017 0.4453 0.1592 0.057 Uiso 1 1 calc R . . . .
H23B H 0.1262 0.5287 0.2410 0.057 Uiso 1 1 calc R . . . .
C24 C 0.0902(3) 0.6253(7) 0.1276(5) 0.055(2) Uani 1 1 d . . . . .
H24A H 0.0467 0.6314 0.1100 0.066 Uiso 1 1 calc R . . . .
H24B H 0.0854 0.6120 0.0739 0.066 Uiso 1 1 calc R . . . .
C25 C 0.1269(4) 0.7436(7) 0.1716(5) 0.052(2) Uani 1 1 d . . . . .
H25A H 0.1263 0.7618 0.2205 0.063 Uiso 1 1 calc R . . . .
H25B H 0.1040 0.8085 0.1279 0.063 Uiso 1 1 calc R . . . .
C26 C 0.1984(3) 0.7415(6) 0.2082(4) 0.0409(17) Uani 1 1 d . . . . .
C27 C 0.2317(3) 0.6291(6) 0.2686(4) 0.0351(16) Uani 1 1 d . . . . .
H27 H 0.2284 0.6412 0.3162 0.042 Uiso 1 1 calc R . . . .
C28 C 0.3055(3) 0.6186(6) 0.3183(4) 0.0418(17) Uani 1 1 d . . . . .
H28A H 0.3125 0.5965 0.2761 0.050 Uiso 1 1 calc R . . . .
H28B H 0.3261 0.6965 0.3440 0.050 Uiso 1 1 calc R . . . .
C29 C 0.3370(3) 0.5244(6) 0.3922(4) 0.0447(18) Uani 1 1 d . . . . .
H29A H 0.3329 0.5501 0.4368 0.054 Uiso 1 1 calc R . . . .
H29B H 0.3833 0.5194 0.4213 0.054 Uiso 1 1 calc R . . . .
C30 C 0.3066(3) 0.3994(6) 0.3580(4) 0.0359(17) Uani 1 1 d . . . . .
C31 C 0.2329(3) 0.4106(5) 0.3035(4) 0.0333(16) Uani 1 1 d . . . . .
H31 H 0.2272 0.4413 0.3461 0.040 Uiso 1 1 calc R . . . .
C32 C 0.1973(3) 0.5054(6) 0.2256(4) 0.0360(17) Uani 1 1 d . . . . .
C33 C 0.2037(3) 0.2835(5) 0.2801(4) 0.0378(17) Uani 1 1 d . . . . .
H33A H 0.1565 0.2882 0.2438 0.045 Uiso 1 1 calc R . . . .
H33B H 0.2139 0.2412 0.2460 0.045 Uiso 1 1 calc R . . . .
C34 C 0.2322(3) 0.2159(6) 0.3658(5) 0.0410(18) Uani 1 1 d . . . . .
H34 H 0.2174 0.2564 0.3956 0.049 Uiso 1 1 calc R . . . .
C35 C 0.3069(4) 0.2124(6) 0.4317(4) 0.0431(18) Uani 1 1 d . . . . .
C38 C 0.3350(3) 0.1162(6) 0.4089(4) 0.0490(19) Uani 1 1 d . . . . .
H38A H 0.3127 0.1179 0.3457 0.073 Uiso 1 1 calc GR . . . .
H38B H 0.3293 0.0381 0.4252 0.073 Uiso 1 1 calc GR . . . .
H38C H 0.3808 0.1313 0.4414 0.073 Uiso 1 1 calc GR . . . .
C39 C 0.3257(3) 0.3470(6) 0.3040(4) 0.0385(16) Uani 1 1 d . . . . .
H39A H 0.3024 0.2717 0.2761 0.046 Uiso 1 1 calc R . . . .
H39B H 0.3136 0.4032 0.2570 0.046 Uiso 1 1 calc R . . . .
C40 C 0.2315(4) 0.8523(7) 0.2669(5) 0.058(2) Uani 1 1 d . . . . .
H40A H 0.2323 0.8459 0.3180 0.070 Uiso 1 1 calc R . . . .
H40B H 0.2764 0.8557 0.2894 0.070 Uiso 1 1 calc R . . . .
C41 C 0.2020(3) 0.7497(6) 0.1319(4) 0.050(2) Uani 1 1 d . . . . .
H41A H 0.1751 0.6877 0.0884 0.076 Uiso 1 1 calc GR . . . .
H41B H 0.2465 0.7387 0.1556 0.076 Uiso 1 1 calc GR . . . .
H41C H 0.1868 0.8277 0.1038 0.076 Uiso 1 1 calc GR . . . .
C42 C 0.1947(3) 0.4655(6) 0.1471(4) 0.0449(18) Uani 1 1 d . . . . .
H42A H 0.1887 0.3794 0.1397 0.067 Uiso 1 1 calc GR . . . .
H42B H 0.2349 0.4871 0.1592 0.067 Uiso 1 1 calc GR . . . .
H42C H 0.1588 0.5051 0.0932 0.067 Uiso 1 1 calc GR . . . .
C43 C 0.4291(4) 0.3809(6) 0.3409(5) 0.0430(19) Uani 1 1 d . . . . .
C44 C 0.4999(3) 0.3516(8) 0.4040(4) 0.055(2) Uani 1 1 d . . . . .
H44A H 0.5172 0.3529 0.3725 0.082 Uiso 1 1 calc GR . . . .
H44B H 0.5059 0.2725 0.4289 0.082 Uiso 1 1 calc GR . . . .
H44C H 0.5224 0.4105 0.4514 0.082 Uiso 1 1 calc GR . . . .
C36A C 0.3269(6) 0.1844(12) 0.5223(6) 0.059(3) Uiso 0.83 1 d . . . A 1
H36A H 0.3179 0.1070 0.5309 0.071 Uiso 0.83 1 calc R . . A 1
C37 C 0.3547(6) 0.2556(11) 0.5872(7) 0.095(4) Uani 0.83 1 d . . . A 1
H37A H 0.3647 0.3339 0.5816 0.114 Uiso 0.83 1 calc R . . A 1
H37B H 0.3654 0.2303 0.6412 0.114 Uiso 0.83 1 calc R . . A 1
C36B C 0.340(3) 0.208(6) 0.532(2) 0.059(3) Uiso 0.17 1 d . . . A 2
H36B H 0.3746 0.2622 0.5695 0.071 Uiso 0.17 1 calc R . . A 2
C37B C 0.325(3) 0.137(5) 0.568(4) 0.099(19) Uiso 0.17 1 d . . . A 2
H37C H 0.2914 0.0815 0.5325 0.119 Uiso 0.17 1 calc R . . A 2
H37D H 0.3479 0.1396 0.6292 0.119 Uiso 0.17 1 calc R . . A 2
O1 O 0.5920(2) -0.4258(4) 0.3128(4) 0.0632(15) Uani 1 1 d . . . . .
H1 H 0.5707 -0.4887 0.2963 0.095 Uiso 1 1 calc GR . . . .
O2 O 0.2308(2) 0.1097(5) 0.1310(3) 0.0577(14) Uani 1 1 d . . . . .
H2 H 0.2236 0.0672 0.1589 0.087 Uiso 1 1 calc GR . . . .
O3 O 0.3324(2) 0.0753(4) 0.0625(3) 0.0389(11) Uani 1 1 d . . . . .
O4 O 0.4286(3) 0.2428(4) 0.1255(3) 0.0569(14) Uani 1 1 d . . . . .
O5 O 0.5070(3) 0.3634(5) 0.2327(4) 0.0691(16) Uani 1 1 d . . . . .
C1 C 0.4299(3) -0.1832(6) 0.3243(4) 0.0435(18) Uani 1 1 d . . . . .
H1A H 0.4135 -0.1417 0.3510 0.052 Uiso 1 1 calc R . . . .
H1B H 0.3943 -0.2313 0.2747 0.052 Uiso 1 1 calc R . . . .
C2 C 0.4852(4) -0.2675(7) 0.3938(5) 0.056(2) Uani 1 1 d . . . . .
H2A H 0.4686 -0.3270 0.4121 0.067 Uiso 1 1 calc R . . . .
H2B H 0.5190 -0.2210 0.4463 0.067 Uiso 1 1 calc R . . . .
C3 C 0.5146(3) -0.3322(7) 0.3563(5) 0.051(2) Uani 1 1 d . . . . .
H3A H 0.4821 -0.3866 0.3088 0.061 Uiso 1 1 calc R . . . .
H3B H 0.5514 -0.3810 0.4034 0.061 Uiso 1 1 calc R . . . .
C4 C 0.5380(3) -0.2462(6) 0.3190(5) 0.0439(18) Uani 1 1 d . . . . .
C5 C 0.4821(3) -0.1573(6) 0.2535(4) 0.0371(16) Uani 1 1 d . . . . .
H5 H 0.4468 -0.2101 0.2064 0.045 Uiso 1 1 calc R . . . .
C6 C 0.4954(3) -0.0731(6) 0.2028(5) 0.0455(19) Uani 1 1 d . . . . .
H6A H 0.5252 -0.0093 0.2426 0.055 Uiso 1 1 calc R . . . .
H6B H 0.5160 -0.1189 0.1835 0.055 Uiso 1 1 calc R . . . .
C7 C 0.4320(3) -0.0172(6) 0.1214(4) 0.0412(18) Uani 1 1 d . . . . .
H7A H 0.4419 0.0366 0.0915 0.049 Uiso 1 1 calc R . . . .
H7B H 0.4038 -0.0810 0.0795 0.049 Uiso 1 1 calc R . . . .
C8 C 0.3959(3) 0.0529(6) 0.1459(4) 0.0380(18) Uani 1 1 d . . . . .
C9 C 0.3878(3) -0.0284(6) 0.2037(4) 0.0346(16) Uani 1 1 d . . . . .
H9 H 0.3618 -0.0970 0.1644 0.042 Uiso 1 1 calc R . . . .
C10 C 0.4505(3) -0.0881(6) 0.2876(4) 0.0347(16) Uani 1 1 d . . . . .
C11 C 0.3428(3) 0.0352(6) 0.2164(4) 0.0416(18) Uani 1 1 d . . . . .
H11A H 0.3390 -0.0123 0.2553 0.050 Uiso 1 1 calc R . . . .
H11B H 0.3605 0.1140 0.2436 0.050 Uiso 1 1 calc R . . . .
C12 C 0.2768(3) 0.0492(6) 0.1256(4) 0.0409(18) Uani 1 1 d . . . . .
H12 H 0.2598 -0.0321 0.1013 0.049 Uiso 1 1 calc R . . . .
C13 C 0.2789(3) 0.1192(6) 0.0579(4) 0.0410(17) Uani 1 1 d . . . . .
C14 C 0.2197(4) 0.0859(7) -0.0366(5) 0.056(2) Uani 1 1 d . . . . .
H14 H 0.2283 0.0339 -0.0661 0.068 Uiso 1 1 calc R . . . .
C15 C 0.1619(5) 0.1165(11) -0.0809(6) 0.121(4) Uani 1 1 d . . . . .
H15A H 0.1492 0.1684 -0.0562 0.145 Uiso 1 1 calc R . . . .
H15B H 0.1309 0.0876 -0.1391 0.145 Uiso 1 1 calc R . . . .
C16 C 0.2828(4) 0.2545(6) 0.0735(5) 0.057(2) Uani 1 1 d . . . . .
H16A H 0.3167 0.2715 0.1360 0.085 Uiso 1 1 calc GR . . . .
H16B H 0.2416 0.2830 0.0558 0.085 Uiso 1 1 calc GR . . . .
H16C H 0.2924 0.2948 0.0387 0.085 Uiso 1 1 calc GR . . . .
C17 C 0.4323(3) 0.1719(6) 0.1910(4) 0.0432(18) Uani 1 1 d . . . . .
H17A H 0.4122 0.2149 0.2120 0.052 Uiso 1 1 calc R . . . .
H17B H 0.4776 0.1557 0.2419 0.052 Uiso 1 1 calc R . . . .
C18 C 0.5490(3) -0.3264(6) 0.2636(5) 0.053(2) Uani 1 1 d . . . . .
H18A H 0.5070 -0.3573 0.2118 0.064 Uiso 1 1 calc R . . . .
H18B H 0.5668 -0.2767 0.2419 0.064 Uiso 1 1 calc R . . . .
C19 C 0.6031(3) -0.1878(7) 0.3939(5) 0.060(2) Uani 1 1 d . . . . .
H19A H 0.6001 -0.1520 0.4367 0.090 Uiso 1 1 calc GR . . . .
H19B H 0.6135 -0.1264 0.3692 0.090 Uiso 1 1 calc GR . . . .
H19C H 0.6369 -0.2483 0.4230 0.090 Uiso 1 1 calc GR . . . .
C20 C 0.4963(3) 0.0038(6) 0.3629(4) 0.052(2) Uani 1 1 d . . . . .
H20A H 0.5236 -0.0375 0.4195 0.078 Uiso 1 1 calc GR . . . .
H20B H 0.4706 0.0639 0.3643 0.078 Uiso 1 1 calc GR . . . .
H20C H 0.5233 0.0423 0.3518 0.078 Uiso 1 1 calc GR . . . .
C21 C 0.4685(4) 0.3358(7) 0.1552(6) 0.0514(19) Uani 1 1 d . . . . .
C22 C 0.4596(4) 0.4026(7) 0.0810(5) 0.078(3) Uani 1 1 d . . . . .
H22A H 0.4213 0.4528 0.0511 0.116 Uiso 1 1 calc GR . . . .
H22B H 0.4544 0.3459 0.0391 0.116 Uiso 1 1 calc GR . . . .
H22C H 0.4972 0.4524 0.1050 0.116 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.0664(3) 0.1246(6) 0.0736(4) 0.1085(19) Uani 0.5 1 d . . . B 1
C45 C 0.0000 0.200(3) 0.0000 0.086(8) Uani 0.5 2 d S T P B 1
H45 H -0.0085 0.2518 0.0322 0.103 Uiso 0.5 1 d R . . B 1
Cl2 Cl 0.0000 0.348(2) 0.0000 0.109(8) Uani 0.25 2 d S T P C 2
Cl3 Cl 0.0635(7) 0.2072(15) 0.0145(11) 0.116(4) Uani 0.25 1 d . . . C 2
Cl4 Cl 0.0283(15) 0.301(3) -0.019(2) 0.107(11) Uani 0.125 1 d . . . C 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O6 H6 0.8200 . ?
O6 C40 1.436(8) . ?
O7 H7 0.8200 . ?
O7 C34 1.431(8) . ?
O8 C30 1.438(7) . ?
O8 C35 1.438(8) . ?
O9 C39 1.452(6) . ?
O9 C43 1.336(7) . ?
O10 C43 1.193(8) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.511(9) . ?
C23 C32 1.558(9) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.525(10) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.538(9) . ?
C26 C27 1.540(8) . ?
C26 C40 1.513(9) . ?
C26 C41 1.532(8) . ?
C27 H27 0.9800 . ?
C27 C28 1.536(8) . ?
C27 C32 1.556(8) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.517(8) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.521(9) . ?
C30 C31 1.521(8) . ?
C30 C39 1.525(8) . ?
C31 H31 0.9800 . ?
C31 C32 1.565(8) . ?
C31 C33 1.525(8) . ?
C32 C42 1.531(8) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C34 1.508(8) . ?
C34 H34 0.9800 . ?
C34 C35 1.528(9) . ?
C35 C38 1.508(9) . ?
C35 C36A 1.499(10) . ?
C35 C36B 1.53(3) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 C44 1.482(9) . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C36A H36A 0.9300 . ?
C36A C37 1.249(14) . ?
C37 H37A 0.9300 . ?
C37 H37B 0.9300 . ?
C36B H36B 0.9300 . ?
C36B C37B 1.26(3) . ?
C37B H37C 0.9300 . ?
C37B H37D 0.9300 . ?
O1 H1 0.8200 . ?
O1 C18 1.425(8) . ?
O2 H2 0.8200 . ?
O2 C12 1.444(7) . ?
O3 C8 1.430(7) . ?
O3 C13 1.439(7) . ?
O4 C17 1.432(7) . ?
O4 C21 1.314(8) . ?
O5 C21 1.198(8) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.523(9) . ?
C1 C10 1.541(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.528(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.534(9) . ?
C4 C5 1.543(9) . ?
C4 C18 1.545(9) . ?
C4 C19 1.520(9) . ?
C5 H5 0.9800 . ?
C5 C6 1.538(8) . ?
C5 C10 1.547(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.523(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.513(8) . ?
C8 C9 1.545(8) . ?
C8 C17 1.532(9) . ?
C9 H9 0.9800 . ?
C9 C10 1.550(8) . ?
C9 C11 1.523(8) . ?
C10 C20 1.542(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.504(8) . ?
C12 H12 0.9800 . ?
C12 C13 1.544(8) . ?
C13 C14 1.514(9) . ?
C13 C16 1.515(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.233(10) . ?
C15 H15A 0.9300 . ?
C15 H15B 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
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 1.486(9) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
Cl1 C45 1.619(15) . ?
C45 Cl1 1.619(15) 2 ?
C45 H45 0.9701 . ?

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
C40 O6 H6 109.5 . . ?
C34 O7 H7 109.5 . . ?
C35 O8 C30 120.8(5) . . ?
C43 O9 C39 116.5(5) . . ?
H23A C23 H23B 107.8 . . ?
C24 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
C24 C23 C32 113.0(5) . . ?
C32 C23 H23A 109.0 . . ?
C32 C23 H23B 109.0 . . ?
C23 C24 H24A 109.3 . . ?
C23 C24 H24B 109.3 . . ?
C23 C24 C25 111.5(6) . . ?
H24A C24 H24B 108.0 . . ?
C25 C24 H24A 109.3 . . ?
C25 C24 H24B 109.3 . . ?
C24 C25 H25A 108.8 . . ?
C24 C25 H25B 108.8 . . ?
C24 C25 C26 113.9(6) . . ?
H25A C25 H25B 107.7 . . ?
C26 C25 H25A 108.8 . . ?
C26 C25 H25B 108.8 . . ?
C25 C26 C27 107.9(5) . . ?
C40 C26 C25 106.9(6) . . ?
C40 C26 C27 107.6(5) . . ?
C40 C26 C41 108.2(5) . . ?
C41 C26 C25 111.0(6) . . ?
C41 C26 C27 114.8(5) . . ?
C26 C27 H27 104.5 . . ?
C26 C27 C32 116.3(5) . . ?
C28 C27 C26 115.2(5) . . ?
C28 C27 H27 104.5 . . ?
C28 C27 C32 110.4(5) . . ?
C32 C27 H27 104.5 . . ?
C27 C28 H28A 109.3 . . ?
C27 C28 H28B 109.3 . . ?
H28A C28 H28B 108.0 . . ?
C29 C28 C27 111.4(5) . . ?
C29 C28 H28A 109.3 . . ?
C29 C28 H28B 109.3 . . ?
C28 C29 H29A 109.0 . . ?
C28 C29 H29B 109.0 . . ?
C28 C29 C30 112.9(5) . . ?
H29A C29 H29B 107.8 . . ?
C30 C29 H29A 109.0 . . ?
C30 C29 H29B 109.0 . . ?
O8 C30 C29 104.8(5) . . ?
O8 C30 C31 109.0(5) . . ?
O8 C30 C39 112.1(5) . . ?
C29 C30 C31 108.7(5) . . ?
C29 C30 C39 109.2(5) . . ?
C31 C30 C39 112.8(5) . . ?
C30 C31 H31 104.6 . . ?
C30 C31 C32 116.6(5) . . ?
C30 C31 C33 108.4(5) . . ?
C32 C31 H31 104.6 . . ?
C33 C31 H31 104.6 . . ?
C33 C31 C32 116.6(5) . . ?
C23 C32 C31 108.1(5) . . ?
C27 C32 C23 106.6(5) . . ?
C27 C32 C31 106.4(5) . . ?
C42 C32 C23 108.0(5) . . ?
C42 C32 C27 115.1(5) . . ?
C42 C32 C31 112.2(5) . . ?
C31 C33 H33A 109.9 . . ?
C31 C33 H33B 109.9 . . ?
H33A C33 H33B 108.3 . . ?
C34 C33 C31 108.8(5) . . ?
C34 C33 H33A 109.9 . . ?
C34 C33 H33B 109.9 . . ?
O7 C34 C33 111.0(6) . . ?
O7 C34 H34 107.8 . . ?
O7 C34 C35 108.0(5) . . ?
C33 C34 H34 107.8 . . ?
C33 C34 C35 114.2(5) . . ?
C35 C34 H34 107.8 . . ?
O8 C35 C34 110.0(5) . . ?
O8 C35 C38 111.3(5) . . ?
O8 C35 C36A 107.1(7) . . ?
O8 C35 C36B 94(2) . . ?
C34 C35 C36B 117(3) . . ?
C38 C35 C34 112.8(6) . . ?
C38 C35 C36B 110(3) . . ?
C36A C35 C34 107.1(6) . . ?
C36A C35 C38 108.3(7) . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O9 C39 C30 109.9(5) . . ?
O9 C39 H39A 109.7 . . ?
O9 C39 H39B 109.7 . . ?
C30 C39 H39A 109.7 . . ?
C30 C39 H39B 109.7 . . ?
H39A C39 H39B 108.2 . . ?
O6 C40 C26 111.5(6) . . ?
O6 C40 H40A 109.3 . . ?
O6 C40 H40B 109.3 . . ?
C26 C40 H40A 109.3 . . ?
C26 C40 H40B 109.3 . . ?
H40A C40 H40B 108.0 . . ?
C26 C41 H41A 109.5 . . ?
C26 C41 H41B 109.5 . . ?
C26 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C32 C42 H42A 109.5 . . ?
C32 C42 H42B 109.5 . . ?
C32 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
O9 C43 C44 112.3(6) . . ?
O10 C43 O9 122.5(7) . . ?
O10 C43 C44 125.2(7) . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C35 C36A H36A 117.1 . . ?
C37 C36A C35 125.9(11) . . ?
C37 C36A H36A 117.1 . . ?
C36A C37 H37A 120.0 . . ?
C36A C37 H37B 120.0 . . ?
H37A C37 H37B 120.0 . . ?
C35 C36B H36B 117.5 . . ?
C37B C36B C35 125(5) . . ?
C37B C36B H36B 117.5 . . ?
C36B C37B H37C 120.0 . . ?
C36B C37B H37D 120.0 . . ?
H37C C37B H37D 120.0 . . ?
C18 O1 H1 109.5 . . ?
C12 O2 H2 109.5 . . ?
C8 O3 C13 122.3(5) . . ?
C21 O4 C17 116.9(5) . . ?
H1A C1 H1B 107.7 . . ?
C2 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
C2 C1 C10 113.5(5) . . ?
C10 C1 H1A 108.9 . . ?
C10 C1 H1B 108.9 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C1 C2 C3 111.2(5) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C2 C3 C4 113.7(6) . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C3 C4 C5 108.5(5) . . ?
C3 C4 C18 105.7(6) . . ?
C5 C4 C18 107.4(5) . . ?
C19 C4 C3 111.5(6) . . ?
C19 C4 C5 115.4(6) . . ?
C19 C4 C18 107.8(5) . . ?
C4 C5 H5 103.6 . . ?
C4 C5 C10 117.3(5) . . ?
C6 C5 C4 114.9(5) . . ?
C6 C5 H5 103.6 . . ?
C6 C5 C10 111.6(5) . . ?
C10 C5 H5 103.6 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 C5 110.9(5) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C6 112.6(5) . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
O3 C8 C7 105.1(5) . . ?
O3 C8 C9 108.2(5) . . ?
O3 C8 C17 111.0(5) . . ?
C7 C8 C9 109.0(5) . . ?
C7 C8 C17 108.9(5) . . ?
C17 C8 C9 114.4(5) . . ?
C8 C9 H9 104.0 . . ?
C8 C9 C10 117.2(5) . . ?
C10 C9 H9 104.0 . . ?
C11 C9 C8 108.7(5) . . ?
C11 C9 H9 104.0 . . ?
C11 C9 C10 117.1(5) . . ?
C1 C10 C5 107.3(5) . . ?
C1 C10 C9 108.3(5) . . ?
C1 C10 C20 108.2(5) . . ?
C5 C10 C9 105.8(5) . . ?
C20 C10 C5 114.3(5) . . ?
C20 C10 C9 112.7(5) . . ?
C9 C11 H11A 110.1 . . ?
C9 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
C12 C11 C9 108.0(5) . . ?
C12 C11 H11A 110.1 . . ?
C12 C11 H11B 110.1 . . ?
O2 C12 C11 111.8(5) . . ?
O2 C12 H12 107.8 . . ?
O2 C12 C13 107.8(5) . . ?
C11 C12 H12 107.8 . . ?
C11 C12 C13 113.6(5) . . ?
C13 C12 H12 107.8 . . ?
O3 C13 C12 109.5(5) . . ?
O3 C13 C14 102.7(5) . . ?
O3 C13 C16 112.3(5) . . ?
C14 C13 C12 109.4(5) . . ?
C14 C13 C16 111.5(6) . . ?
C16 C13 C12 111.1(6) . . ?
C13 C14 H14 114.7 . . ?
C15 C14 C13 130.6(8) . . ?
C15 C14 H14 114.7 . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 C8 107.5(5) . . ?
O4 C17 H17A 110.2 . . ?
O4 C17 H17B 110.2 . . ?
C8 C17 H17A 110.2 . . ?
C8 C17 H17B 110.2 . . ?
H17A C17 H17B 108.5 . . ?
O1 C18 C4 113.6(6) . . ?
O1 C18 H18A 108.9 . . ?
O1 C18 H18B 108.9 . . ?
C4 C18 H18A 108.9 . . ?
C4 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C21 C22 111.8(7) . . ?
O5 C21 O4 123.9(7) . . ?
O5 C21 C22 124.3(7) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Cl1 C45 Cl1 118.5(18) . 2 ?
Cl1 C45 H45 107.7 2 . ?
Cl1 C45 H45 107.7 . . ?

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
O7 C34 C35 O8 167.9(5) . . . . ?
O7 C34 C35 C38 42.9(7) . . . . ?
O7 C34 C35 C36A -76.1(8) . . . . ?
O7 C34 C35 C36B -87(3) . . . . ?
O8 C30 C31 C32 167.2(5) . . . . ?
O8 C30 C31 C33 -58.8(6) . . . . ?
O8 C30 C39 O9 -49.7(7) . . . . ?
O8 C35 C36A C37 7.0(16) . . . . ?
O8 C35 C36B C37B 163(6) . . . . ?
C23 C24 C25 C26 55.0(8) . . . . ?
C24 C23 C32 C27 54.6(7) . . . . ?
C24 C23 C32 C31 168.7(5) . . . . ?
C24 C23 C32 C42 -69.6(7) . . . . ?
C24 C25 C26 C27 -51.9(7) . . . . ?
C24 C25 C26 C40 -167.4(5) . . . . ?
C24 C25 C26 C41 74.8(7) . . . . ?
C25 C26 C27 C28 -174.5(5) . . . . ?
C25 C26 C27 C32 54.1(7) . . . . ?
C25 C26 C40 O6 -56.8(7) . . . . ?
C26 C27 C28 C29 166.1(5) . . . . ?
C26 C27 C32 C23 -55.3(6) . . . . ?
C26 C27 C32 C31 -170.5(5) . . . . ?
C26 C27 C32 C42 64.6(7) . . . . ?
C27 C26 C40 O6 -172.5(5) . . . . ?
C27 C28 C29 C30 57.8(7) . . . . ?
C28 C27 C32 C23 171.2(5) . . . . ?
C28 C27 C32 C31 55.9(6) . . . . ?
C28 C27 C32 C42 -69.0(6) . . . . ?
C28 C29 C30 O8 -168.8(5) . . . . ?
C28 C29 C30 C31 -52.4(7) . . . . ?
C28 C29 C30 C39 70.9(7) . . . . ?
C29 C30 C31 C32 53.6(7) . . . . ?
C29 C30 C31 C33 -172.5(5) . . . . ?
C29 C30 C39 O9 66.0(7) . . . . ?
C30 O8 C35 C34 -44.7(7) . . . . ?
C30 O8 C35 C38 81.1(7) . . . . ?
C30 O8 C35 C36A -160.7(7) . . . . ?
C30 O8 C35 C36B -166(3) . . . . ?
C30 C31 C32 C23 -169.9(5) . . . . ?
C30 C31 C32 C27 -55.7(7) . . . . ?
C30 C31 C32 C42 71.1(7) . . . . ?
C30 C31 C33 C34 61.2(6) . . . . ?
C31 C30 C39 O9 -173.1(5) . . . . ?
C31 C33 C34 O7 -177.0(5) . . . . ?
C31 C33 C34 C35 -54.7(7) . . . . ?
C32 C23 C24 C25 -56.5(8) . . . . ?
C32 C27 C28 C29 -59.7(6) . . . . ?
C32 C31 C33 C34 -164.9(5) . . . . ?
C33 C31 C32 C23 60.0(7) . . . . ?
C33 C31 C32 C27 174.2(5) . . . . ?
C33 C31 C32 C42 -59.1(7) . . . . ?
C33 C34 C35 O8 43.9(7) . . . . ?
C33 C34 C35 C38 -81.1(7) . . . . ?
C33 C34 C35 C36A 159.9(7) . . . . ?
C33 C34 C35 C36B 149(3) . . . . ?
C34 C35 C36A C37 -111.0(13) . . . . ?
C34 C35 C36B C37B 48(7) . . . . ?
C35 O8 C30 C29 169.6(5) . . . . ?
C35 O8 C30 C31 53.5(7) . . . . ?
C35 O8 C30 C39 -72.1(7) . . . . ?
C38 C35 C36A C37 127.1(13) . . . . ?
C38 C35 C36B C37B -83(6) . . . . ?
C39 O9 C43 O10 -1.7(10) . . . . ?
C39 O9 C43 C44 -179.4(5) . . . . ?
C39 C30 C31 C32 -67.6(7) . . . . ?
C39 C30 C31 C33 66.3(7) . . . . ?
C40 C26 C27 C28 -59.4(7) . . . . ?
C40 C26 C27 C32 169.2(5) . . . . ?
C41 C26 C27 C28 61.1(7) . . . . ?
C41 C26 C27 C32 -70.3(7) . . . . ?
C41 C26 C40 O6 62.9(7) . . . . ?
C43 O9 C39 C30 -122.2(6) . . . . ?
C36A C35 C36B C37B 2(8) . . . . ?
C36B C35 C36A C37 27(12) . . . . ?
O2 C12 C13 O3 169.7(5) . . . . ?
O2 C12 C13 C14 -78.5(7) . . . . ?
O2 C12 C13 C16 45.1(7) . . . . ?
O3 C8 C9 C10 166.6(5) . . . . ?
O3 C8 C9 C11 -57.9(6) . . . . ?
O3 C8 C17 O4 -50.2(7) . . . . ?
O3 C13 C14 C15 -168.5(10) . . . . ?
C1 C2 C3 C4 55.0(8) . . . . ?
C2 C1 C10 C5 53.5(7) . . . . ?
C2 C1 C10 C9 167.3(5) . . . . ?
C2 C1 C10 C20 -70.2(7) . . . . ?
C2 C3 C4 C5 -50.9(7) . . . . ?
C2 C3 C4 C18 -165.8(6) . . . . ?
C2 C3 C4 C19 77.3(7) . . . . ?
C3 C4 C5 C6 -173.9(6) . . . . ?
C3 C4 C5 C10 51.9(7) . . . . ?
C3 C4 C18 O1 -54.7(7) . . . . ?
C4 C5 C6 C7 162.9(5) . . . . ?
C4 C5 C10 C1 -52.9(7) . . . . ?
C4 C5 C10 C9 -168.3(5) . . . . ?
C4 C5 C10 C20 67.1(7) . . . . ?
C5 C4 C18 O1 -170.4(5) . . . . ?
C5 C6 C7 C8 57.6(7) . . . . ?
C6 C5 C10 C1 171.6(5) . . . . ?
C6 C5 C10 C9 56.1(6) . . . . ?
C6 C5 C10 C20 -68.5(7) . . . . ?
C6 C7 C8 O3 -167.5(5) . . . . ?
C6 C7 C8 C9 -51.7(7) . . . . ?
C6 C7 C8 C17 73.6(7) . . . . ?
C7 C8 C9 C10 52.9(7) . . . . ?
C7 C8 C9 C11 -171.6(5) . . . . ?
C7 C8 C17 O4 64.9(7) . . . . ?
C8 O3 C13 C12 -44.2(7) . . . . ?
C8 O3 C13 C14 -160.4(5) . . . . ?
C8 O3 C13 C16 79.7(7) . . . . ?
C8 C9 C10 C1 -169.2(5) . . . . ?
C8 C9 C10 C5 -54.4(7) . . . . ?
C8 C9 C10 C20 71.2(7) . . . . ?
C8 C9 C11 C12 62.9(7) . . . . ?
C9 C8 C17 O4 -172.9(5) . . . . ?
C9 C11 C12 O2 -179.6(5) . . . . ?
C9 C11 C12 C13 -57.3(7) . . . . ?
C10 C1 C2 C3 -56.6(8) . . . . ?
C10 C5 C6 C7 -60.4(7) . . . . ?
C10 C9 C11 C12 -161.5(5) . . . . ?
C11 C9 C10 C1 58.9(7) . . . . ?
C11 C9 C10 C5 173.7(5) . . . . ?
C11 C9 C10 C20 -60.7(7) . . . . ?
C11 C12 C13 O3 45.2(7) . . . . ?
C11 C12 C13 C14 157.0(6) . . . . ?
C11 C12 C13 C16 -79.4(7) . . . . ?
C12 C13 C14 C15 75.3(12) . . . . ?
C13 O3 C8 C7 167.7(5) . . . . ?
C13 O3 C8 C9 51.4(7) . . . . ?
C13 O3 C8 C17 -74.8(6) . . . . ?
C16 C13 C14 C15 -48.1(12) . . . . ?
C17 O4 C21 O5 0.1(11) . . . . ?
C17 O4 C21 C22 -179.5(6) . . . . ?
C17 C8 C9 C10 -69.2(7) . . . . ?
C17 C8 C9 C11 66.4(7) . . . . ?
C18 C4 C5 C6 -60.1(7) . . . . ?
C18 C4 C5 C10 165.8(5) . . . . ?
C19 C4 C5 C6 60.2(8) . . . . ?
C19 C4 C5 C10 -74.0(7) . . . . ?
C19 C4 C18 O1 64.7(7) . . . . ?
C21 O4 C17 C8 -165.4(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_compound_14

_audit_creation_date             2014-07-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_shelxl_version_number           2013-2
_chemical_name_common            'crotonlaevin M'
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H30 O4'
_chemical_formula_sum            'C20 H30 O4'
_chemical_formula_weight         334.44
_chemical_absolute_configuration ad
_chemical_optical_rotation       '[\a]^26^~D~=+10.0 (c 0.10, in CHCl3)'
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   9.1613(4)
_cell_length_b                   11.8102(7)
_cell_length_c                   16.9960(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.829(5)
_cell_angle_gamma                90
_cell_volume                     1829.40(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8009
_cell_measurement_temperature    290(1)
_cell_measurement_theta_max      72.6904
_cell_measurement_theta_min      6.1284
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17362
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.844
_diffrn_reflns_theta_min         6.133
_diffrn_ambient_temperature      290(1)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -71.00  -43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000 -150.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega  -77.00  -39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -150.0000 38

#__ type_ start__ end____ width___ exp.time_
  3 omega  -61.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
  4 omega  -12.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
  5 omega  -81.00  -52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -180.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  -80.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -30.0000 45

#__ type_ start__ end____ width___ exp.time_
  7 omega  -91.00  -12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  125.0000 -120.0000 79

#__ type_ start__ end____ width___ exp.time_
  8 omega -131.00  -79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -99.0000  -30.0000 52

#__ type_ start__ end____ width___ exp.time_
  9 omega -130.00  -79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000 -125.0000  120.0000 51

#__ type_ start__ end____ width___ exp.time_
 10 omega  -67.00  -41.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -57.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega -117.00  -80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -99.0000   60.0000 37

#__ type_ start__ end____ width___ exp.time_
 12 omega  -64.00  -34.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -57.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
 13 omega -130.00 -104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000 -101.0000   43.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega -125.00  -99.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -57.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   26.00   51.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 16 omega -129.00  -33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -77.0000 -180.0000 96

#__ type_ start__ end____ width___ exp.time_
 17 omega  -58.00  -32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega  -49.00    9.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   38.0000   90.0000 58

#__ type_ start__ end____ width___ exp.time_
 19 omega -126.00  -86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -63.0000  -90.0000 40

#__ type_ start__ end____ width___ exp.time_
 20 omega -124.00  -32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -77.0000 -150.0000 92

#__ type_ start__ end____ width___ exp.time_
 21 omega  -70.00  -40.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -63.0000  -90.0000 30

#__ type_ start__ end____ width___ exp.time_
 22 omega   83.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   71.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -101.0000   31.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega  100.00  149.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000    0.0000 49

#__ type_ start__ end____ width___ exp.time_
 25 omega   83.00  131.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000 -180.0000 48

#__ type_ start__ end____ width___ exp.time_
 26 omega   87.00  135.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000 -120.0000 48

#__ type_ start__ end____ width___ exp.time_
 27 omega  117.00  155.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000 -180.0000 38

#__ type_ start__ end____ width___ exp.time_
 28 omega  131.00  169.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000  120.0000 38

#__ type_ start__ end____ width___ exp.time_
 29 omega   61.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000 -120.0000 41

#__ type_ start__ end____ width___ exp.time_
 30 omega   83.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 31 omega   91.00  118.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 32 omega  122.00  149.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 33 omega   67.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -63.0000 -180.0000 46

#__ type_ start__ end____ width___ exp.time_
 34 omega  133.00  159.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 35 omega  152.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 36 omega  115.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   76.0000 -135.0670 62

#__ type_ start__ end____ width___ exp.time_
 37 omega   86.00  122.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000  -60.0000 36

#__ type_ start__ end____ width___ exp.time_
 38 omega   51.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000 -180.0000 37

#__ type_ start__ end____ width___ exp.time_
 39 omega  100.00  125.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 40 omega  123.00  149.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -12.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 41 omega   44.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -12.0000 -180.0000 63

#__ type_ start__ end____ width___ exp.time_
 42 omega  138.00  164.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 43 omega  106.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000  -30.0000 70

#__ type_ start__ end____ width___ exp.time_
 44 omega  144.00  170.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 45 omega   90.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000  -90.0000 36

#__ type_ start__ end____ width___ exp.time_
 46 omega   85.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   38.0000 -180.0000 41

#__ type_ start__ end____ width___ exp.time_
 47 omega   83.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 48 omega  125.00  165.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   25.0000  -90.0000 40

#__ type_ start__ end____ width___ exp.time_
 49 omega   61.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 50 omega   45.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000  -60.0000 48

#__ type_ start__ end____ width___ exp.time_
 51 omega   83.00  152.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   76.0000  -81.6663 69

#__ type_ start__ end____ width___ exp.time_
 52 omega   90.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 53 omega  139.00  165.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 54 omega   96.00  130.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
 55 omega   48.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000 -180.0000 46

#__ type_ start__ end____ width___ exp.time_
 56 omega   43.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000  -60.0000 49

#__ type_ start__ end____ width___ exp.time_
 57 omega   52.00   79.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 58 omega   92.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 59 omega   47.00   76.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
 60 omega   44.00   81.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000 -120.0000 37

#__ type_ start__ end____ width___ exp.time_
 61 omega   93.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000 -180.0000 85

#__ type_ start__ end____ width___ exp.time_
 62 omega   83.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 63 omega  104.00  130.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 64 omega   64.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -91.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 65 omega   89.00  120.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   65.0000  174.4279 31

#__ type_ start__ end____ width___ exp.time_
 66 omega   92.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   63.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 67 omega   93.00  124.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000 -120.0000 31

#__ type_ start__ end____ width___ exp.time_
 68 omega   83.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   76.0000 -135.0670 25

#__ type_ start__ end____ width___ exp.time_
 69 omega   88.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   25.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 70 omega   80.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   33.0000 -116.8183 30

#__ type_ start__ end____ width___ exp.time_
 71 omega  -82.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   30.0000 48

#__ type_ start__ end____ width___ exp.time_
 72 omega  -82.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  120.0000 48

#__ type_ start__ end____ width___ exp.time_
 73 omega  -73.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000   60.0000 104

#__ type_ start__ end____ width___ exp.time_
 74 omega  -72.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000    0.0000 105

#__ type_ start__ end____ width___ exp.time_
 75 omega -130.00  -25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -77.0000    0.0000 105

#__ type_ start__ end____ width___ exp.time_
 76 omega  -74.00   13.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000   57.0000 -150.0000 87

#__ type_ start__ end____ width___ exp.time_
 77 omega -130.00  -73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000 -125.0000 -180.0000 57

#__ type_ start__ end____ width___ exp.time_
 78 omega -130.00  -25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -77.0000   60.0000 105

#__ type_ start__ end____ width___ exp.time_
 79 omega -131.00  -27.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -38.0000   60.0000 104

#__ type_ start__ end____ width___ exp.time_
 80 omega -130.00  -25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -77.0000  -60.0000 105

#__ type_ start__ end____ width___ exp.time_
 81 omega    4.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000 -101.0000   31.0000 100

#__ type_ start__ end____ width___ exp.time_
 82 omega   25.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  150.0000 105

#__ type_ start__ end____ width___ exp.time_
 83 omega -137.00  -31.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -77.0000  120.0000 106

#__ type_ start__ end____ width___ exp.time_
 84 omega   42.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000   30.0000 74

#__ type_ start__ end____ width___ exp.time_
 85 omega   72.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   25.0000    0.0000 106

#__ type_ start__ end____ width___ exp.time_
 86 omega   43.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000  -30.0000 50

#__ type_ start__ end____ width___ exp.time_
 87 omega   44.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -50.0000   60.0000 60

#__ type_ start__ end____ width___ exp.time_
 88 omega   83.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000   30.0000 95

#__ type_ start__ end____ width___ exp.time_
 89 omega   42.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -101.0000 -136.0000 70

#__ type_ start__ end____ width___ exp.time_
 90 omega   41.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000   90.0000 53

#__ type_ start__ end____ width___ exp.time_
 91 omega   80.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   33.0000  137.0506 98

#__ type_ start__ end____ width___ exp.time_
 92 omega   77.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   29.0000   35.0000 101

#__ type_ start__ end____ width___ exp.time_
 93 omega   42.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000   90.0000 74

#__ type_ start__ end____ width___ exp.time_
 94 omega   42.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000  -30.0000 74

#__ type_ start__ end____ width___ exp.time_
 95 omega   87.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   69.0000   18.3623 91

#__ type_ start__ end____ width___ exp.time_
 96 omega   82.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   35.0000   94.4299 96
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1627586000
_diffrn_orient_matrix_UB_12      0.0351445000
_diffrn_orient_matrix_UB_13      -0.0079062000
_diffrn_orient_matrix_UB_21      0.0121076000
_diffrn_orient_matrix_UB_22      0.0376982000
_diffrn_orient_matrix_UB_23      -0.0857702000
_diffrn_orient_matrix_UB_31      -0.0436607000
_diffrn_orient_matrix_UB_32      -0.1198725000
_diffrn_orient_matrix_UB_33      -0.0297805000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_full    0.922
_reflns_Friedel_fraction_max     0.911
_reflns_number_gt                3475
_reflns_number_total             3503
_reflns_odcompleteness_completeness 97.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1560 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3503
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0613P)²+0.3229P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0920
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H4-O4
 0.82 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4A), C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C12(H12A,H12B), C14(H14A,H14B), C15(H15A,H15B),
 C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C11(H11)
3.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C)
3.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.50753(16) 0.58827(16) 0.36881(9) 0.0472(4) Uani 1 1 d . . . . .
O2 O 0.31058(15) 0.52644(16) 0.29845(10) 0.0498(4) Uani 1 1 d . . . . .
O3 O 0.40811(14) 0.28442(13) 0.24259(8) 0.0376(3) Uani 1 1 d . . . . .
H3 H 0.4809 0.2530 0.2647 0.056 Uiso 1 1 calc GR . . . .
O4 O 0.88949(18) 0.67274(17) 0.65061(9) 0.0515(4) Uani 1 1 d D . . . .
C1 C 0.77308(17) 0.44002(15) 0.19644(9) 0.0271(3) Uani 1 1 d . . . . .
C20 C 0.6806(4) 0.7882(3) 0.41997(16) 0.0711(9) Uani 1 1 d . . . . .
H20A H 0.7238 0.8015 0.3717 0.107 Uiso 1 1 calc GR . . . .
H20B H 0.7215 0.8399 0.4598 0.107 Uiso 1 1 calc GR . . . .
H20C H 0.5764 0.7994 0.4111 0.107 Uiso 1 1 calc GR . . . .
C2 C 0.45220(17) 0.38169(15) 0.20113(10) 0.0283(4) Uani 1 1 d . . . . .
H2 H 0.3630 0.4203 0.1785 0.034 Uiso 1 1 calc R . . . .
C3 C 0.54037(19) 0.35013(17) 0.13331(10) 0.0313(4) Uani 1 1 d . . . . .
H3A H 0.5344 0.4109 0.0948 0.038 Uiso 1 1 calc R . . . .
H3B H 0.4990 0.2826 0.1074 0.038 Uiso 1 1 calc R . . . .
C4 C 0.70052(18) 0.32875(15) 0.16297(10) 0.0273(3) Uani 1 1 d . . . . .
H4A H 0.6969 0.2797 0.2093 0.033 Uiso 1 1 calc R . . . .
C5 C 0.4435(2) 0.52529(18) 0.30943(11) 0.0353(4) Uani 1 1 d . . . . .
C6 C 0.67828(18) 0.48775(15) 0.25760(9) 0.0271(3) Uani 1 1 d . . . . .
C7 C 0.7434(2) 0.57466(18) 0.31593(11) 0.0362(4) Uani 1 1 d . . . . .
H7A H 0.7362 0.6491 0.2917 0.043 Uiso 1 1 calc R . . . .
H7B H 0.8465 0.5580 0.3298 0.043 Uiso 1 1 calc R . . . .
C8 C 0.6650(2) 0.57509(18) 0.38983(11) 0.0364(4) Uani 1 1 d . . . . .
H8 H 0.6824 0.5023 0.4169 0.044 Uiso 1 1 calc R . . . .
C9 C 0.53550(18) 0.46294(15) 0.25772(10) 0.0277(3) Uani 1 1 d . . . . .
C10 C 0.7120(2) 0.66869(19) 0.44700(11) 0.0389(4) Uani 1 1 d . . . . .
C11 C 0.7815(3) 0.6432(2) 0.51650(12) 0.0475(5) Uani 1 1 d . . . . .
H11 H 0.7968 0.5668 0.5276 0.057 Uiso 1 1 calc R . . . .
C12 C 0.8383(4) 0.7259(2) 0.57931(14) 0.0616(7) Uani 1 1 d . . . . .
H12A H 0.9175 0.7694 0.5605 0.074 Uiso 1 1 calc R . . . .
H12B H 0.7604 0.7782 0.5889 0.074 Uiso 1 1 calc R . . . .
C13 C 0.7877(2) 0.25953(17) 0.10571(11) 0.0364(4) Uani 1 1 d . . . . .
C14 C 0.9432(2) 0.2416(2) 0.14621(14) 0.0447(5) Uani 1 1 d . . . . .
H14A H 0.9384 0.1891 0.1898 0.054 Uiso 1 1 calc R . . . .
H14B H 1.0024 0.2068 0.1087 0.054 Uiso 1 1 calc R . . . .
C15 C 1.0191(2) 0.3487(2) 0.17763(14) 0.0454(5) Uani 1 1 d . . . . .
H15A H 1.0352 0.3980 0.1337 0.055 Uiso 1 1 calc R . . . .
H15B H 1.1141 0.3295 0.2049 0.055 Uiso 1 1 calc R . . . .
C16 C 0.9285(2) 0.4114(2) 0.23448(12) 0.0412(5) Uani 1 1 d . . . . .
H16A H 0.9785 0.4809 0.2515 0.049 Uiso 1 1 calc R . . . .
H16B H 0.9210 0.3649 0.2809 0.049 Uiso 1 1 calc R . . . .
C17 C 0.7166(3) 0.1420(2) 0.09378(18) 0.0570(6) Uani 1 1 d . . . . .
H17A H 0.6974 0.1116 0.1441 0.085 Uiso 1 1 calc GR . . . .
H17B H 0.7819 0.0924 0.0695 0.085 Uiso 1 1 calc GR . . . .
H17C H 0.6261 0.1486 0.0603 0.085 Uiso 1 1 calc GR . . . .
C18 C 0.7916(3) 0.3137(2) 0.02380(12) 0.0483(6) Uani 1 1 d . . . . .
H18A H 0.6949 0.3389 0.0045 0.073 Uiso 1 1 calc GR . . . .
H18B H 0.8249 0.2589 -0.0121 0.073 Uiso 1 1 calc GR . . . .
H18C H 0.8574 0.3771 0.0278 0.073 Uiso 1 1 calc GR . . . .
C19 C 0.7829(2) 0.53636(18) 0.13556(11) 0.0381(4) Uani 1 1 d . . . . .
H19A H 0.6892 0.5458 0.1054 0.057 Uiso 1 1 calc GR . . . .
H19B H 0.8553 0.5175 0.1006 0.057 Uiso 1 1 calc GR . . . .
H19C H 0.8102 0.6056 0.1628 0.057 Uiso 1 1 calc GR . . . .
H4 H 0.821(3) 0.634(3) 0.662(2) 0.079(11) Uiso 1 1 d D . . . .


_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 1.340(2) . ?
O1 C8 1.458(2) . ?
O2 C5 1.213(2) . ?
O3 C2 1.427(2) . ?
O4 C12 1.403(3) . ?
C1 C4 1.554(2) . ?
C1 C6 1.528(2) . ?
C1 C16 1.540(2) . ?
C1 C19 1.547(2) . ?
C20 C10 1.503(4) . ?
C2 C3 1.520(2) . ?
C2 C9 1.510(2) . ?
C3 C4 1.523(2) . ?
C4 C13 1.553(2) . ?
C5 C9 1.475(2) . ?
C6 C7 1.507(2) . ?
C6 C9 1.341(2) . ?
C7 C8 1.509(2) . ?
C8 C10 1.506(3) . ?
C10 C11 1.319(3) . ?
C11 C12 1.500(3) . ?
C13 C14 1.532(3) . ?
C13 C17 1.538(3) . ?
C13 C18 1.536(3) . ?
C14 C15 1.514(4) . ?
C15 C16 1.528(3) . ?

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 118.12(15) . . ?
C6 C1 C4 108.02(13) . . ?
C6 C1 C16 111.12(14) . . ?
C6 C1 C19 105.04(14) . . ?
C16 C1 C4 108.11(15) . . ?
C16 C1 C19 109.17(15) . . ?
C19 C1 C4 115.39(14) . . ?
O3 C2 C3 112.09(15) . . ?
O3 C2 C9 110.31(14) . . ?
C9 C2 C3 111.46(14) . . ?
C2 C3 C4 110.98(13) . . ?
C3 C4 C1 110.05(15) . . ?
C3 C4 C13 114.80(14) . . ?
C13 C4 C1 116.51(14) . . ?
O1 C5 C9 119.56(16) . . ?
O2 C5 O1 117.72(18) . . ?
O2 C5 C9 122.64(18) . . ?
C7 C6 C1 118.95(14) . . ?
C9 C6 C1 122.85(15) . . ?
C9 C6 C7 117.96(15) . . ?
C6 C7 C8 111.07(15) . . ?
O1 C8 C7 109.83(15) . . ?
O1 C8 C10 106.90(16) . . ?
C10 C8 C7 114.23(16) . . ?
C5 C9 C2 114.49(14) . . ?
C6 C9 C2 124.62(15) . . ?
C6 C9 C5 120.56(16) . . ?
C20 C10 C8 117.31(19) . . ?
C11 C10 C20 123.2(2) . . ?
C11 C10 C8 119.4(2) . . ?
C10 C11 C12 126.1(2) . . ?
O4 C12 C11 112.6(2) . . ?
C14 C13 C4 107.75(15) . . ?
C14 C13 C17 107.27(19) . . ?
C14 C13 C18 111.01(17) . . ?
C17 C13 C4 108.64(16) . . ?
C18 C13 C4 114.18(17) . . ?
C18 C13 C17 107.75(19) . . ?
C15 C14 C13 114.59(17) . . ?
C14 C15 C16 111.59(17) . . ?
C15 C16 C1 112.30(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1002245'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_compound_15

_database_code_depnum_ccdc_archive 'CCDC 1002246'
_audit_creation_date             2012-09-25
_audit_creation_method           
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_chemical_name_common            'crotonlaevin N'
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H30 O3'
_chemical_formula_sum            'C20 H30 O3'
_chemical_formula_weight         318.44
_chemical_absolute_configuration ad
_chemical_optical_rotation       '[\a]^23^~D~=-18.75 (c 0.32, in CHCl3)'
_chemical_melting_point          398
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   7.1319(6)
_cell_length_b                   14.3359(11)
_cell_length_c                   17.4859(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1787.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2258
_cell_measurement_temperature    291.4(1)
_cell_measurement_theta_max      72.5354
_cell_measurement_theta_min      3.9842
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4991
_diffrn_reflns_theta_full        70.07
_diffrn_reflns_theta_max         70.07
_diffrn_reflns_theta_min         3.99
_diffrn_ambient_temperature      291.44(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9731
_diffrn_measured_fraction_theta_max 0.9811
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -30.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  116.0000  158.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega  -73.00  -47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -79.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -90.0000 43

#__ type_ start__ end____ width___ exp.time_
  4 omega -126.00 -101.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000 -125.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega -132.00  -97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -99.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
  6 omega -129.00  -99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000 -125.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
  7 omega  -43.00    5.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000   50.0000 -150.0000 48

#__ type_ start__ end____ width___ exp.time_
  8 omega -115.00  -89.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -91.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega -132.00  -87.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -91.0000  -60.0000 45

#__ type_ start__ end____ width___ exp.time_
 10 omega   54.00   87.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega  109.00  145.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000  -60.0000 36

#__ type_ start__ end____ width___ exp.time_
 12 omega   65.00   92.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 13 omega   41.00   94.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
 14 omega   44.00   74.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
 15 omega   45.00   83.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000 -120.0000 38

#__ type_ start__ end____ width___ exp.time_
 16 omega   88.00  114.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   67.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega  138.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000  150.0000 38

#__ type_ start__ end____ width___ exp.time_
 19 omega   94.00  119.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 20 omega  146.00  172.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   12.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega  107.00  133.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 22 omega  148.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000    0.0000 30

#__ type_ start__ end____ width___ exp.time_
 23 omega  102.00  128.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   12.0000    0.0000 26
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1552537000
_diffrn_orient_matrix_UB_12      0.0601983000
_diffrn_orient_matrix_UB_13      -0.0362686000
_diffrn_orient_matrix_UB_21      0.0916529000
_diffrn_orient_matrix_UB_22      -0.0124182000
_diffrn_orient_matrix_UB_23      -0.0791319000
_diffrn_orient_matrix_UB_31      -0.1190502000
_diffrn_orient_matrix_UB_32      -0.0881069000
_diffrn_orient_matrix_UB_33      -0.0136956000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2703
_reflns_number_total             2976
_reflns_odcompleteness_completeness 97.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2976
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0528P)²+0.1181P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1019
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.22892(18) 0.67682(8) 0.55845(7) 0.0415(3) Uani 1 1 d . . .
O3 O 0.21134(19) 0.71448(8) 0.40170(8) 0.0455(3) Uani 1 1 d . . .
H3 H 0.1303 0.7545 0.3961 0.068 Uiso 1 1 calc R . .
O2 O 0.4616(2) 0.64192(11) 0.63399(10) 0.0610(4) Uani 1 1 d . . .
C1 C 0.3158(3) 0.61691(12) 0.60504(10) 0.0408(4) Uani 1 1 d . . .
C9 C 0.0641(3) 0.65117(11) 0.51376(10) 0.0372(4) Uani 1 1 d . . .
H9 H -0.0127 0.7078 0.5109 0.045 Uiso 1 1 calc R . .
C14 C 0.1280(2) 0.63135(11) 0.43059(10) 0.0369(4) Uani 1 1 d . . .
C7 C 0.0561(2) 0.49332(11) 0.57852(9) 0.0347(3) Uani 1 1 d . . .
H7 H 0.0992 0.4643 0.5309 0.042 Uiso 1 1 calc R . .
C15 C 0.2773(3) 0.55671(12) 0.42563(10) 0.0451(4) Uani 1 1 d . . .
H15 H 0.2372 0.4950 0.4249 0.054 Uiso 1 1 calc R . .
C8 C -0.0547(3) 0.58015(12) 0.55615(11) 0.0407(4) Uani 1 1 d . . .
H8A H -0.1593 0.5619 0.5240 0.049 Uiso 1 1 calc R . .
H8B H -0.1053 0.6088 0.6019 0.049 Uiso 1 1 calc R . .
C2 C 0.2285(2) 0.52428(11) 0.62144(10) 0.0355(3) Uani 1 1 d . . .
C5 C 0.0913(3) 0.34110(12) 0.64413(10) 0.0440(4) Uani 1 1 d . . .
H5 H 0.1614 0.3302 0.5968 0.053 Uiso 1 1 calc R . .
C6 C -0.0554(3) 0.41768(12) 0.62327(10) 0.0392(4) Uani 1 1 d . . .
C3 C 0.3064(3) 0.47391(14) 0.67705(12) 0.0470(4) Uani 1 1 d . . .
H3A H 0.4096 0.4982 0.7027 0.056 Uiso 1 1 calc R . .
C18 C -0.1496(3) 0.46058(14) 0.69402(11) 0.0497(5) Uani 1 1 d . . .
H18A H -0.0566 0.4907 0.7251 0.075 Uiso 1 1 calc R . .
H18B H -0.2098 0.4123 0.7231 0.075 Uiso 1 1 calc R . .
H18C H -0.2413 0.5056 0.6781 0.075 Uiso 1 1 calc R . .
C4 C 0.2349(3) 0.38008(13) 0.69997(12) 0.0512(5) Uani 1 1 d . . .
H4A H 0.1783 0.3846 0.7503 0.061 Uiso 1 1 calc R . .
H4B H 0.3397 0.3371 0.7035 0.061 Uiso 1 1 calc R . .
C10 C 0.0161(4) 0.24306(13) 0.66797(11) 0.0587(6) Uani 1 1 d . . .
C19 C -0.0637(4) 0.23834(16) 0.74983(12) 0.0651(7) Uani 1 1 d . . .
H19A H 0.0281 0.2612 0.7853 0.098 Uiso 1 1 calc R . .
H19B H -0.0942 0.1749 0.7621 0.098 Uiso 1 1 calc R . .
H19C H -0.1748 0.2760 0.7530 0.098 Uiso 1 1 calc R . .
C17 C -0.0413(3) 0.60437(17) 0.38206(12) 0.0556(5) Uani 1 1 d . . .
H17A H -0.1400 0.6489 0.3898 0.083 Uiso 1 1 calc R . .
H17B H -0.0841 0.5435 0.3968 0.083 Uiso 1 1 calc R . .
H17C H -0.0063 0.6038 0.3291 0.083 Uiso 1 1 calc R . .
C16 C 0.4552(4) 0.57133(18) 0.42226(18) 0.0649(6) Uani 1 1 d . . .
C20 C 0.1820(5) 0.17335(15) 0.66437(18) 0.0915(11) Uani 1 1 d . . .
H20A H 0.2485 0.1815 0.6171 0.137 Uiso 1 1 calc R . .
H20B H 0.1348 0.1107 0.6673 0.137 Uiso 1 1 calc R . .
H20C H 0.2654 0.1846 0.7065 0.137 Uiso 1 1 calc R . .
C11 C -0.1337(5) 0.21273(17) 0.61093(14) 0.0851(10) Uani 1 1 d . . .
H11A H -0.0740 0.1996 0.5622 0.102 Uiso 1 1 calc R . .
H11B H -0.1904 0.1553 0.6289 0.102 Uiso 1 1 calc R . .
C13 C -0.2045(4) 0.37641(17) 0.56937(13) 0.0656(7) Uani 1 1 d . . .
H13A H -0.3050 0.4213 0.5631 0.079 Uiso 1 1 calc R . .
H13B H -0.1485 0.3660 0.5195 0.079 Uiso 1 1 calc R . .
C12 C -0.2867(5) 0.2846(2) 0.59859(17) 0.0884(10) Uani 1 1 d . . .
H12A H -0.3521 0.2955 0.6464 0.106 Uiso 1 1 calc R . .
H12B H -0.3768 0.2609 0.5618 0.106 Uiso 1 1 calc R . .
H16A H 0.545(5) 0.520(2) 0.4172(18) 0.095(10) Uiso 1 1 d . . .
H16B H 0.505(4) 0.633(2) 0.4241(17) 0.086(9) Uiso 1 1 d . . .


_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 C1 1.336(2) . ?
O1 C9 1.459(2) . ?
O3 C14 1.424(2) . ?
O2 C1 1.211(2) . ?
C1 C2 1.495(2) . ?
C9 C14 1.550(2) . ?
C9 C8 1.518(2) . ?
C14 C15 1.512(2) . ?
C14 C17 1.526(3) . ?
C7 C8 1.525(2) . ?
C7 C2 1.507(2) . ?
C7 C6 1.556(2) . ?
C15 C16 1.288(3) . ?
C2 C3 1.333(3) . ?
C5 C6 1.560(3) . ?
C5 C4 1.522(3) . ?
C5 C10 1.561(2) . ?
C6 C18 1.536(3) . ?
C6 C13 1.539(3) . ?
C3 C4 1.493(2) . ?
C10 C19 1.542(3) . ?
C10 C20 1.550(4) . ?
C10 C11 1.525(4) . ?
C11 C12 1.517(5) . ?
C13 C12 1.529(3) . ?

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
C1 O1 C9 122.58(13) . . ?
O1 C1 C2 119.65(15) . . ?
O2 C1 O1 117.58(16) . . ?
O2 C1 C2 122.74(17) . . ?
O1 C9 C14 108.16(14) . . ?
O1 C9 C8 110.92(13) . . ?
C8 C9 C14 119.95(14) . . ?
O3 C14 C9 107.58(14) . . ?
O3 C14 C15 106.14(14) . . ?
O3 C14 C17 110.18(15) . . ?
C15 C14 C9 113.00(14) . . ?
C15 C14 C17 110.25(16) . . ?
C17 C14 C9 109.60(15) . . ?
C8 C7 C6 115.67(15) . . ?
C2 C7 C8 108.04(13) . . ?
C2 C7 C6 111.82(13) . . ?
C16 C15 C14 125.55(19) . . ?
C9 C8 C7 112.58(14) . . ?
C1 C2 C7 120.41(14) . . ?
C3 C2 C1 116.60(16) . . ?
C3 C2 C7 122.94(15) . . ?
C6 C5 C10 117.77(18) . . ?
C4 C5 C6 110.08(14) . . ?
C4 C5 C10 112.98(16) . . ?
C7 C6 C5 105.39(15) . . ?
C18 C6 C7 110.45(14) . . ?
C18 C6 C5 112.76(15) . . ?
C18 C6 C13 110.19(18) . . ?
C13 C6 C7 108.23(14) . . ?
C13 C6 C5 109.63(17) . . ?
C2 C3 C4 122.82(18) . . ?
C3 C4 C5 112.84(16) . . ?
C19 C10 C5 114.47(16) . . ?
C19 C10 C20 106.9(2) . . ?
C20 C10 C5 107.9(2) . . ?
C11 C10 C5 108.82(18) . . ?
C11 C10 C19 109.6(2) . . ?
C11 C10 C20 108.9(2) . . ?
C12 C11 C10 113.8(2) . . ?
C12 C13 C6 113.04(19) . . ?
C11 C12 C13 110.9(2) . . ?

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_compound_16

_database_code_depnum_ccdc_archive 'CCDC 1002247'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'crotonlaevin O'
_chemical_melting_point          440.7
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H30 O3'
_chemical_formula_weight         318.44
_chemical_absolute_configuration unk
_chemical_optical_rotation       '[\a]^20^~D~=+30.00 (c 0.3, in CHCl3)'

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

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

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

_cell_length_a                   15.646(17)
_cell_length_b                   10.703(12)
_cell_length_c                   10.876(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1821(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3384
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      22.11

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9827
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12994
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3376
_reflns_number_gt                2621
_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)+(0.0411P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0207(17)
_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   -1.3(12)
_refine_ls_number_reflns         3376
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0921
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
C1 C -0.01849(13) 0.2878(2) 0.98373(16) 0.0545(5) Uani 1 1 d . . .
H1A H -0.0591 0.2193 0.9852 0.065 Uiso 1 1 calc R . .
H1B H -0.0478 0.3605 0.9513 0.065 Uiso 1 1 calc R . .
C2 C 0.00996(16) 0.3155(2) 1.11538(17) 0.0686(7) Uani 1 1 d . . .
H2A H 0.0461 0.3891 1.1160 0.082 Uiso 1 1 calc R . .
H2B H -0.0398 0.3326 1.1659 0.082 Uiso 1 1 calc R . .
C3 C 0.05859(15) 0.2058(2) 1.16841(18) 0.0639(6) Uani 1 1 d . . .
H3A H 0.0204 0.1346 1.1737 0.077 Uiso 1 1 calc R . .
H3B H 0.0765 0.2265 1.2513 0.077 Uiso 1 1 calc R . .
C4 C 0.13719(13) 0.1685(2) 1.09359(17) 0.0507(5) Uani 1 1 d . . .
C5 C 0.10883(11) 0.14783(18) 0.95734(16) 0.0419(5) Uani 1 1 d . . .
H5 H 0.0700 0.0761 0.9607 0.050 Uiso 1 1 calc R . .
C6 C 0.18156(13) 0.1053(2) 0.87374(18) 0.0576(6) Uani 1 1 d . . .
H6A H 0.2301 0.1602 0.8861 0.069 Uiso 1 1 calc R . .
H6B H 0.1988 0.0218 0.8980 0.069 Uiso 1 1 calc R . .
C7 C 0.15961(12) 0.10396(19) 0.74039(18) 0.0486(5) Uani 1 1 d . . .
H7 H 0.1996 0.0714 0.6858 0.058 Uiso 1 1 calc R . .
C8 C 0.08626(11) 0.14657(17) 0.69475(16) 0.0363(4) Uani 1 1 d . . .
C9 C 0.01690(10) 0.19691(16) 0.77749(14) 0.0345(4) Uani 1 1 d . . .
H9 H -0.0177 0.1250 0.8028 0.041 Uiso 1 1 calc R . .
C10 C 0.05509(11) 0.25370(16) 0.89711(16) 0.0381(5) Uani 1 1 d . . .
C11 C -0.04177(11) 0.28136(18) 0.70209(15) 0.0409(5) Uani 1 1 d . . .
H11A H -0.0908 0.3059 0.7510 0.049 Uiso 1 1 calc R . .
H11B H -0.0113 0.3563 0.6777 0.049 Uiso 1 1 calc R . .
C12 C -0.07097(10) 0.21074(18) 0.58968(16) 0.0394(4) Uani 1 1 d . . .
H12 H -0.0956 0.1312 0.6168 0.047 Uiso 1 1 calc R . .
C13 C -0.13695(10) 0.27705(19) 0.50881(16) 0.0419(5) Uani 1 1 d . . .
C14 C -0.10566(14) 0.4012(2) 0.4631(2) 0.0564(6) Uani 1 1 d . . .
H14 H -0.0583 0.3998 0.4115 0.068 Uiso 1 1 calc R . .
C15 C -0.13701(18) 0.5087(3) 0.4874(3) 0.1000(10) Uani 1 1 d . . .
H15A H -0.1844 0.5155 0.5385 0.120 Uiso 1 1 calc R . .
H15B H -0.1124 0.5801 0.4539 0.120 Uiso 1 1 calc R . .
C16 C -0.15986(14) 0.1945(2) 0.39899(18) 0.0598(6) Uani 1 1 d . . .
H16A H -0.1771 0.1135 0.4277 0.090 Uiso 1 1 calc R . .
H16B H -0.1109 0.1861 0.3463 0.090 Uiso 1 1 calc R . .
H16C H -0.2059 0.2321 0.3539 0.090 Uiso 1 1 calc R . .
C17 C 0.07637(11) 0.14822(18) 0.55943(16) 0.0402(5) Uani 1 1 d . . .
C18 C 0.17097(17) 0.0445(2) 1.1450(2) 0.0735(7) Uani 1 1 d . . .
H18A H 0.1771 0.0510 1.2326 0.110 Uiso 1 1 calc R . .
H18B H 0.2255 0.0261 1.1088 0.110 Uiso 1 1 calc R . .
H18C H 0.1314 -0.0213 1.1259 0.110 Uiso 1 1 calc R . .
C19 C 0.20797(16) 0.2668(2) 1.1110(2) 0.0760(7) Uani 1 1 d . . .
H19A H 0.1866 0.3476 1.0883 0.114 Uiso 1 1 calc R . .
H19B H 0.2560 0.2460 1.0599 0.114 Uiso 1 1 calc R . .
H19C H 0.2255 0.2680 1.1955 0.114 Uiso 1 1 calc R . .
C20 C 0.10774(14) 0.36998(18) 0.86531(18) 0.0549(6) Uani 1 1 d . . .
H20A H 0.0736 0.4261 0.8170 0.082 Uiso 1 1 calc R . .
H20B H 0.1574 0.3457 0.8192 0.082 Uiso 1 1 calc R . .
H20C H 0.1252 0.4109 0.9397 0.082 Uiso 1 1 calc R . .
O1 O 0.13326(8) 0.12162(14) 0.48755(12) 0.0569(4) Uani 1 1 d . . .
O2 O 0.00142(7) 0.18331(12) 0.51024(10) 0.0470(4) Uani 1 1 d . . .
O3 O -0.20741(8) 0.28899(18) 0.58996(12) 0.0662(5) Uani 1 1 d . . .
H3 H -0.2478 0.3206 0.5533 0.099 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
C1 C10 1.532(3) . ?
C1 C2 1.529(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.513(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.528(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C18 1.535(3) . ?
C4 C19 1.539(3) . ?
C4 C5 1.563(3) . ?
C5 C6 1.526(3) . ?
C5 C10 1.556(3) . ?
C5 H5 0.9800 . ?
C6 C7 1.490(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.331(3) . ?
C7 H7 0.9300 . ?
C8 C17 1.480(3) . ?
C8 C9 1.509(2) . ?
C9 C11 1.527(2) . ?
C9 C10 1.555(3) . ?
C9 H9 0.9800 . ?
C10 C20 1.532(3) . ?
C11 C12 1.508(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O2 1.455(2) . ?
C12 C13 1.531(3) . ?
C12 H12 0.9800 . ?
C13 O3 1.418(2) . ?
C13 C14 1.501(3) . ?
C13 C16 1.528(3) . ?
C14 C15 1.278(4) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9300 . ?
C15 H15B 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O1 1.218(2) . ?
C17 O2 1.343(2) . ?
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 . ?
O3 H3 0.8200 . ?

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
C10 C1 C2 113.79(18) . . ?
C10 C1 H1A 108.8 . . ?
C2 C1 H1A 108.8 . . ?
C10 C1 H1B 108.8 . . ?
C2 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C3 C2 C1 110.67(19) . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C2 C3 C4 113.85(18) . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 C18 108.00(18) . . ?
C3 C4 C19 109.6(2) . . ?
C18 C4 C19 107.38(19) . . ?
C3 C4 C5 108.27(17) . . ?
C18 C4 C5 108.74(18) . . ?
C19 C4 C5 114.69(16) . . ?
C6 C5 C10 111.69(16) . . ?
C6 C5 C4 113.30(17) . . ?
C10 C5 C4 116.72(16) . . ?
C6 C5 H5 104.6 . . ?
C10 C5 H5 104.6 . . ?
C4 C5 H5 104.6 . . ?
C7 C6 C5 114.25(17) . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C8 C7 C6 123.94(18) . . ?
C8 C7 H7 118.0 . . ?
C6 C7 H7 118.0 . . ?
C7 C8 C17 117.72(16) . . ?
C7 C8 C9 121.34(17) . . ?
C17 C8 C9 120.90(16) . . ?
C8 C9 C11 108.87(15) . . ?
C8 C9 C10 111.22(15) . . ?
C11 C9 C10 116.66(16) . . ?
C8 C9 H9 106.5 . . ?
C11 C9 H9 106.5 . . ?
C10 C9 H9 106.5 . . ?
C1 C10 C20 110.47(17) . . ?
C1 C10 C5 108.70(16) . . ?
C20 C10 C5 113.34(17) . . ?
C1 C10 C9 108.58(15) . . ?
C20 C10 C9 109.58(15) . . ?
C5 C10 C9 105.97(15) . . ?
C12 C11 C9 108.71(16) . . ?
C12 C11 H11A 109.9 . . ?
C9 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
C9 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
O2 C12 C11 110.29(15) . . ?
O2 C12 C13 106.11(15) . . ?
C11 C12 C13 115.96(16) . . ?
O2 C12 H12 108.1 . . ?
C11 C12 H12 108.1 . . ?
C13 C12 H12 108.1 . . ?
O3 C13 C14 112.32(18) . . ?
O3 C13 C16 110.87(16) . . ?
C14 C13 C16 109.24(18) . . ?
O3 C13 C12 102.03(16) . . ?
C14 C13 C12 112.38(16) . . ?
C16 C13 C12 109.84(17) . . ?
C15 C14 C13 127.1(3) . . ?
C15 C14 H14 116.4 . . ?
C13 C14 H14 116.4 . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C17 O2 116.60(17) . . ?
O1 C17 C8 123.98(17) . . ?
O2 C17 C8 119.40(15) . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 O2 C12 120.00(15) . . ?
C13 O3 H3 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 -56.7(3) . . . . ?
C1 C2 C3 C4 57.6(3) . . . . ?
C2 C3 C4 C18 -170.70(19) . . . . ?
C2 C3 C4 C19 72.6(2) . . . . ?
C2 C3 C4 C5 -53.1(2) . . . . ?
C3 C4 C5 C6 -177.86(17) . . . . ?
C18 C4 C5 C6 -60.8(2) . . . . ?
C19 C4 C5 C6 59.4(2) . . . . ?
C3 C4 C5 C10 50.3(2) . . . . ?
C18 C4 C5 C10 167.38(17) . . . . ?
C19 C4 C5 C10 -72.4(2) . . . . ?
C10 C5 C6 C7 -36.7(2) . . . . ?
C4 C5 C6 C7 -170.98(18) . . . . ?
C5 C6 C7 C8 5.9(3) . . . . ?
C6 C7 C8 C17 175.3(2) . . . . ?
C6 C7 C8 C9 -2.0(3) . . . . ?
C7 C8 C9 C11 158.73(17) . . . . ?
C17 C8 C9 C11 -18.5(2) . . . . ?
C7 C8 C9 C10 28.8(2) . . . . ?
C17 C8 C9 C10 -148.42(17) . . . . ?
C2 C1 C10 C20 -73.5(2) . . . . ?
C2 C1 C10 C5 51.5(2) . . . . ?
C2 C1 C10 C9 166.32(17) . . . . ?
C6 C5 C10 C1 177.75(16) . . . . ?
C4 C5 C10 C1 -49.7(2) . . . . ?
C6 C5 C10 C20 -59.0(2) . . . . ?
C4 C5 C10 C20 73.6(2) . . . . ?
C6 C5 C10 C9 61.21(19) . . . . ?
C4 C5 C10 C9 -166.20(15) . . . . ?
C8 C9 C10 C1 -172.92(15) . . . . ?
C11 C9 C10 C1 61.4(2) . . . . ?
C8 C9 C10 C20 66.33(19) . . . . ?
C11 C9 C10 C20 -59.3(2) . . . . ?
C8 C9 C10 C5 -56.30(18) . . . . ?
C11 C9 C10 C5 178.02(14) . . . . ?
C8 C9 C11 C12 52.30(19) . . . . ?
C10 C9 C11 C12 179.15(14) . . . . ?
C9 C11 C12 O2 -64.69(19) . . . . ?
C9 C11 C12 C13 174.72(14) . . . . ?
O2 C12 C13 O3 174.64(15) . . . . ?
C11 C12 C13 O3 -62.5(2) . . . . ?
O2 C12 C13 C14 -64.8(2) . . . . ?
C11 C12 C13 C14 58.0(2) . . . . ?
O2 C12 C13 C16 56.98(19) . . . . ?
C11 C12 C13 C16 179.80(15) . . . . ?
O3 C13 C14 C15 -2.0(3) . . . . ?
C16 C13 C14 C15 121.4(3) . . . . ?
C12 C13 C14 C15 -116.4(3) . . . . ?
C7 C8 C17 O1 -5.5(3) . . . . ?
C9 C8 C17 O1 171.81(18) . . . . ?
C7 C8 C17 O2 175.94(17) . . . . ?
C9 C8 C17 O2 -6.7(3) . . . . ?
O1 C17 O2 C12 177.02(17) . . . . ?
C8 C17 O2 C12 -4.3(2) . . . . ?
C11 C12 O2 C17 40.2(2) . . . . ?
C13 C12 O2 C17 166.50(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.030
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_compound_17

_database_code_depnum_ccdc_archive 'CCDC 1002248'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'crotonlaevin P'
_chemical_melting_point          396
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H30 O3'
_chemical_formula_weight         318.44
_chemical_absolute_configuration unk
_chemical_optical_rotation       '[\a]^23^~D~=+32.0 (c 0.25, in CHCl3)'

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

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

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

_cell_length_a                   6.519(2)
_cell_length_b                   17.905(6)
_cell_length_c                   31.128(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3633.2(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2464
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      17.76

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      colorless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9790
_exptl_absorpt_correction_T_max  0.9842
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26369
_diffrn_reflns_av_R_equivalents  0.1056
_diffrn_reflns_av_sigmaI/netI    0.1079
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         25.57
_reflns_number_total             6748
_reflns_number_gt                4160
_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)+(0.1000P)²+0.2744P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(2)
_refine_ls_number_reflns         6748
_refine_ls_number_parameters     425
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1383
_refine_ls_R_factor_gt           0.0809
_refine_ls_wR_factor_ref         0.1940
_refine_ls_wR_factor_gt          0.1654
_refine_ls_goodness_of_fit_ref   0.950
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1659(7) 0.5209(2) 0.01325(14) 0.0425(12) Uani 1 1 d . . .
H1A H 0.1252 0.4897 0.0372 0.051 Uiso 1 1 calc R . .
H1B H 0.0512 0.5533 0.0064 0.051 Uiso 1 1 calc R . .
C2 C 0.2099(8) 0.4711(3) -0.02536(15) 0.0532(14) Uani 1 1 d . . .
H2A H 0.3174 0.4358 -0.0182 0.064 Uiso 1 1 calc R . .
H2B H 0.0876 0.4431 -0.0328 0.064 Uiso 1 1 calc R . .
C3 C 0.2756(8) 0.5177(3) -0.06309(15) 0.0498(13) Uani 1 1 d . . .
H3A H 0.1638 0.5508 -0.0710 0.060 Uiso 1 1 calc R . .
H3B H 0.3017 0.4850 -0.0873 0.060 Uiso 1 1 calc R . .
C4 C 0.4671(7) 0.5646(3) -0.05472(14) 0.0386(11) Uani 1 1 d . . .
C5 C 0.4324(7) 0.6107(2) -0.01308(13) 0.0343(10) Uani 1 1 d . . .
H5 H 0.3243 0.6464 -0.0207 0.041 Uiso 1 1 calc R . .
C6 C 0.6160(7) 0.6598(3) -0.00062(16) 0.0511(14) Uani 1 1 d . . .
H6A H 0.7371 0.6286 0.0019 0.061 Uiso 1 1 calc R . .
H6B H 0.6409 0.6957 -0.0233 0.061 Uiso 1 1 calc R . .
C7 C 0.5835(8) 0.7006(3) 0.04074(16) 0.0478(13) Uani 1 1 d . . .
H7 H 0.6796 0.7367 0.0483 0.057 Uiso 1 1 calc R . .
C8 C 0.4295(7) 0.6894(2) 0.06719(14) 0.0363(11) Uani 1 1 d . . .
C9 C 0.2662(6) 0.6314(2) 0.05787(13) 0.0299(10) Uani 1 1 d . . .
H9 H 0.1556 0.6572 0.0426 0.036 Uiso 1 1 calc R . .
C10 C 0.3472(6) 0.5692(2) 0.02707(13) 0.0304(10) Uani 1 1 d . . .
C11 C 0.1756(7) 0.6045(2) 0.10046(13) 0.0355(11) Uani 1 1 d . . .
H11A H 0.0627 0.5705 0.0949 0.043 Uiso 1 1 calc R . .
H11B H 0.2794 0.5778 0.1166 0.043 Uiso 1 1 calc R . .
C12 C 0.1000(7) 0.6703(2) 0.12628(14) 0.0363(11) Uani 1 1 d . . .
H12 H -0.0050 0.6965 0.1095 0.044 Uiso 1 1 calc R . .
C13 C 0.0099(7) 0.6504(2) 0.17016(14) 0.0380(11) Uani 1 1 d . . .
C14 C -0.1813(8) 0.6060(3) 0.16307(16) 0.0579(14) Uani 1 1 d . . .
H14 H -0.2671 0.6229 0.1413 0.069 Uiso 1 1 calc R . .
C15 C -0.2420(11) 0.5481(3) 0.1829(2) 0.081(2) Uani 1 1 d . . .
H15A H -0.1631 0.5283 0.2051 0.097 Uiso 1 1 calc R . .
H15B H -0.3652 0.5255 0.1753 0.097 Uiso 1 1 calc R . .
C16 C -0.0436(9) 0.7204(3) 0.19576(16) 0.0572(14) Uani 1 1 d . . .
H16A H -0.0989 0.7063 0.2232 0.086 Uiso 1 1 calc R . .
H16B H -0.1434 0.7492 0.1803 0.086 Uiso 1 1 calc R . .
H16C H 0.0779 0.7498 0.2000 0.086 Uiso 1 1 calc R . .
C17 C 0.4212(8) 0.7336(2) 0.10708(15) 0.0398(11) Uani 1 1 d . . .
C18 C 0.4954(9) 0.6183(3) -0.09241(14) 0.0555(15) Uani 1 1 d . . .
H18A H 0.4954 0.5906 -0.1188 0.083 Uiso 1 1 calc R . .
H18B H 0.6236 0.6442 -0.0894 0.083 Uiso 1 1 calc R . .
H18C H 0.3851 0.6538 -0.0927 0.083 Uiso 1 1 calc R . .
C19 C 0.6575(8) 0.5142(3) -0.05381(17) 0.0570(14) Uani 1 1 d . . .
H19A H 0.6427 0.4776 -0.0315 0.085 Uiso 1 1 calc R . .
H19B H 0.7772 0.5440 -0.0484 0.085 Uiso 1 1 calc R . .
H19C H 0.6717 0.4895 -0.0810 0.085 Uiso 1 1 calc R . .
C20 C 0.5087(8) 0.5214(3) 0.05014(15) 0.0488(13) Uani 1 1 d . . .
H20A H 0.4491 0.4995 0.0754 0.073 Uiso 1 1 calc R . .
H20B H 0.6227 0.5523 0.0583 0.073 Uiso 1 1 calc R . .
H20C H 0.5552 0.4826 0.0312 0.073 Uiso 1 1 calc R . .
C21 C 0.0542(8) 0.3906(3) 0.13748(15) 0.0509(13) Uani 1 1 d . . .
H21A H 0.0023 0.4236 0.1597 0.061 Uiso 1 1 calc R . .
H21B H 0.1797 0.4124 0.1264 0.061 Uiso 1 1 calc R . .
C22 C -0.1032(9) 0.3862(3) 0.10127(16) 0.0618(16) Uani 1 1 d . . .
H22A H -0.2320 0.3671 0.1124 0.074 Uiso 1 1 calc R . .
H22B H -0.1275 0.4356 0.0897 0.074 Uiso 1 1 calc R . .
C23 C -0.0250(10) 0.3351(3) 0.06610(16) 0.0600(15) Uani 1 1 d . . .
H23A H 0.0988 0.3566 0.0540 0.072 Uiso 1 1 calc R . .
H23B H -0.1268 0.3330 0.0434 0.072 Uiso 1 1 calc R . .
C24 C 0.0219(8) 0.2556(3) 0.08099(15) 0.0485(13) Uani 1 1 d . . .
C25 C 0.1644(7) 0.2591(2) 0.12116(13) 0.0355(10) Uani 1 1 d . . .
H25 H 0.2949 0.2783 0.1101 0.043 Uiso 1 1 calc R . .
C26 C 0.2174(9) 0.1830(3) 0.13962(16) 0.0574(15) Uani 1 1 d . . .
H26A H 0.0912 0.1561 0.1454 0.069 Uiso 1 1 calc R . .
H26B H 0.2934 0.1549 0.1183 0.069 Uiso 1 1 calc R . .
C27 C 0.3405(8) 0.1866(3) 0.17983(16) 0.0506(13) Uani 1 1 d . . .
H27 H 0.3938 0.1423 0.1908 0.061 Uiso 1 1 calc R . .
C28 C 0.3782(6) 0.2490(2) 0.20073(14) 0.0339(10) Uani 1 1 d . . .
C29 C 0.2961(7) 0.3242(2) 0.18680(13) 0.0323(10) Uani 1 1 d . . .
H29 H 0.4028 0.3475 0.1692 0.039 Uiso 1 1 calc R . .
C30 C 0.1037(7) 0.3147(2) 0.15740(14) 0.0352(10) Uani 1 1 d . . .
C31 C 0.2692(7) 0.3731(2) 0.22607(13) 0.0372(11) Uani 1 1 d . . .
H31A H 0.2224 0.4222 0.2174 0.045 Uiso 1 1 calc R . .
H31B H 0.1661 0.3515 0.2448 0.045 Uiso 1 1 calc R . .
C32 C 0.4685(7) 0.3799(2) 0.24983(14) 0.0342(10) Uani 1 1 d . . .
H32 H 0.5689 0.4033 0.2306 0.041 Uiso 1 1 calc R . .
C33 C 0.4608(7) 0.4253(2) 0.29168(14) 0.0383(11) Uani 1 1 d . . .
C34 C 0.3779(8) 0.5021(3) 0.28210(15) 0.0448(13) Uani 1 1 d . . .
H34 H 0.4445 0.5294 0.2609 0.054 Uiso 1 1 calc R . .
C35 C 0.2245(11) 0.5332(3) 0.30040(17) 0.0648(16) Uani 1 1 d . . .
H35A H 0.1530 0.5080 0.3218 0.078 Uiso 1 1 calc R . .
H35B H 0.1844 0.5810 0.2923 0.078 Uiso 1 1 calc R . .
C36 C 0.6737(9) 0.4328(3) 0.31110(18) 0.0686(16) Uani 1 1 d . . .
H36A H 0.6656 0.4612 0.3372 0.103 Uiso 1 1 calc R . .
H36B H 0.7624 0.4578 0.2911 0.103 Uiso 1 1 calc R . .
H36C H 0.7275 0.3840 0.3172 0.103 Uiso 1 1 calc R . .
C37 C 0.5045(7) 0.2442(3) 0.24034(14) 0.0358(11) Uani 1 1 d . . .
C38 C 0.1388(10) 0.2162(3) 0.04444(17) 0.0760(19) Uani 1 1 d . . .
H38A H 0.2702 0.2394 0.0406 0.114 Uiso 1 1 calc R . .
H38B H 0.0614 0.2200 0.0183 0.114 Uiso 1 1 calc R . .
H38C H 0.1575 0.1645 0.0516 0.114 Uiso 1 1 calc R . .
C39 C -0.1799(9) 0.2125(3) 0.08788(18) 0.0711(18) Uani 1 1 d . . .
H39A H -0.1505 0.1645 0.1001 0.107 Uiso 1 1 calc R . .
H39B H -0.2480 0.2061 0.0608 0.107 Uiso 1 1 calc R . .
H39C H -0.2670 0.2402 0.1070 0.107 Uiso 1 1 calc R . .
C40 C -0.0772(7) 0.2869(3) 0.18472(16) 0.0569(14) Uani 1 1 d . . .
H40A H -0.0436 0.2393 0.1970 0.085 Uiso 1 1 calc R . .
H40B H -0.1967 0.2819 0.1669 0.085 Uiso 1 1 calc R . .
H40C H -0.1044 0.3221 0.2073 0.085 Uiso 1 1 calc R . .
O1 O 0.5485(6) 0.7796(2) 0.11684(11) 0.0644(11) Uani 1 1 d . . .
O2 O 0.2682(5) 0.72198(16) 0.13488(9) 0.0463(8) Uani 1 1 d . . .
O3 O 0.1517(5) 0.60496(17) 0.19300(10) 0.0508(9) Uani 1 1 d . . .
H3 H 0.2275 0.6316 0.2074 0.076 Uiso 1 1 calc R . .
O4 O 0.5753(6) 0.18662(18) 0.25355(11) 0.0548(9) Uani 1 1 d . . .
O5 O 0.5465(5) 0.30659(17) 0.26236(9) 0.0438(8) Uani 1 1 d . . .
O6 O 0.3236(5) 0.39108(17) 0.32101(10) 0.0498(9) Uani 1 1 d . . .
H6 H 0.3825 0.3569 0.3335 0.075 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
C1 C2 1.524(6) . ?
C1 C10 1.526(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.503(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.527(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C18 1.528(6) . ?
C4 C19 1.535(6) . ?
C4 C5 1.553(6) . ?
C5 C6 1.535(6) . ?
C5 C10 1.556(6) . ?
C5 H5 0.9800 . ?
C6 C7 1.496(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.314(6) . ?
C7 H7 0.9300 . ?
C8 C17 1.473(6) . ?
C8 C9 1.515(6) . ?
C9 C11 1.529(6) . ?
C9 C10 1.562(5) . ?
C9 H9 0.9800 . ?
C10 C20 1.534(6) . ?
C11 C12 1.509(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O2 1.459(5) . ?
C12 C13 1.529(6) . ?
C12 H12 0.9800 . ?
C13 O3 1.422(5) . ?
C13 C14 1.495(7) . ?
C13 C16 1.526(6) . ?
C14 C15 1.270(7) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9300 . ?
C15 H15B 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O1 1.209(5) . ?
C17 O2 1.337(5) . ?
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 1.526(7) . ?
C21 C30 1.529(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.514(7) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.529(7) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C39 1.540(7) . ?
C24 C38 1.540(7) . ?
C24 C25 1.559(6) . ?
C25 C26 1.518(6) . ?
C25 C30 1.556(6) . ?
C25 H25 0.9800 . ?
C26 C27 1.488(7) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.317(6) . ?
C27 H27 0.9300 . ?
C28 C37 1.485(6) . ?
C28 C29 1.513(5) . ?
C29 C31 1.513(6) . ?
C29 C30 1.562(6) . ?
C29 H29 0.9800 . ?
C30 C40 1.537(6) . ?
C31 C32 1.500(6) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 O5 1.462(5) . ?
C32 C33 1.536(6) . ?
C32 H32 0.9800 . ?
C33 O6 1.418(5) . ?
C33 C34 1.506(6) . ?
C33 C36 1.520(7) . ?
C34 C35 1.278(7) . ?
C34 H34 0.9300 . ?
C35 H35A 0.9300 . ?
C35 H35B 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 O4 1.203(5) . ?
C37 O5 1.338(5) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
O3 H3 0.8200 . ?
O6 H6 0.8200 . ?

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
C2 C1 C10 114.1(4) . . ?
C2 C1 H1A 108.7 . . ?
C10 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
C10 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C1 110.2(4) . . ?
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 . . ?
C2 C3 C4 113.9(4) . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 C18 108.3(4) . . ?
C3 C4 C19 109.9(4) . . ?
C18 C4 C19 106.7(4) . . ?
C3 C4 C5 108.4(4) . . ?
C18 C4 C5 109.0(4) . . ?
C19 C4 C5 114.5(4) . . ?
C6 C5 C4 113.6(4) . . ?
C6 C5 C10 110.4(3) . . ?
C4 C5 C10 118.0(4) . . ?
C6 C5 H5 104.4 . . ?
C4 C5 H5 104.4 . . ?
C10 C5 H5 104.4 . . ?
C7 C6 C5 112.8(4) . . ?
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 . . ?
C8 C7 C6 124.9(4) . . ?
C8 C7 H7 117.5 . . ?
C6 C7 H7 117.5 . . ?
C7 C8 C17 118.3(4) . . ?
C7 C8 C9 121.5(4) . . ?
C17 C8 C9 120.3(4) . . ?
C8 C9 C11 108.7(3) . . ?
C8 C9 C10 111.6(3) . . ?
C11 C9 C10 116.0(3) . . ?
C8 C9 H9 106.6 . . ?
C11 C9 H9 106.6 . . ?
C10 C9 H9 106.6 . . ?
C1 C10 C20 110.3(4) . . ?
C1 C10 C5 108.7(3) . . ?
C20 C10 C5 113.4(4) . . ?
C1 C10 C9 108.3(3) . . ?
C20 C10 C9 110.0(3) . . ?
C5 C10 C9 105.9(3) . . ?
C12 C11 C9 110.0(3) . . ?
C12 C11 H11A 109.7 . . ?
C9 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C9 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
O2 C12 C11 110.3(3) . . ?
O2 C12 C13 105.8(3) . . ?
C11 C12 C13 114.8(4) . . ?
O2 C12 H12 108.6 . . ?
C11 C12 H12 108.6 . . ?
C13 C12 H12 108.6 . . ?
O3 C13 C14 108.2(4) . . ?
O3 C13 C16 110.9(4) . . ?
C14 C13 C16 108.9(4) . . ?
O3 C13 C12 109.3(4) . . ?
C14 C13 C12 108.2(4) . . ?
C16 C13 C12 111.3(4) . . ?
C15 C14 C13 128.4(6) . . ?
C15 C14 H14 115.8 . . ?
C13 C14 H14 115.8 . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C17 O2 117.1(4) . . ?
O1 C17 C8 123.6(5) . . ?
O2 C17 C8 119.3(4) . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C20 H20A 109.5 . . ?
C10 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C10 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C30 113.2(4) . . ?
C22 C21 H21A 108.9 . . ?
C30 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C30 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C23 C22 C21 109.9(4) . . ?
C23 C22 H22A 109.7 . . ?
C21 C22 H22A 109.7 . . ?
C23 C22 H22B 109.7 . . ?
C21 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C22 C23 C24 114.2(4) . . ?
C22 C23 H23A 108.7 . . ?
C24 C23 H23A 108.7 . . ?
C22 C23 H23B 108.7 . . ?
C24 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
C23 C24 C39 109.7(5) . . ?
C23 C24 C38 107.6(4) . . ?
C39 C24 C38 107.2(4) . . ?
C23 C24 C25 109.0(4) . . ?
C39 C24 C25 114.7(4) . . ?
C38 C24 C25 108.4(4) . . ?
C26 C25 C30 111.0(4) . . ?
C26 C25 C24 113.8(4) . . ?
C30 C25 C24 117.1(4) . . ?
C26 C25 H25 104.5 . . ?
C30 C25 H25 104.5 . . ?
C24 C25 H25 104.5 . . ?
C27 C26 C25 113.7(4) . . ?
C27 C26 H26A 108.8 . . ?
C25 C26 H26A 108.8 . . ?
C27 C26 H26B 108.8 . . ?
C25 C26 H26B 108.8 . . ?
H26A C26 H26B 107.7 . . ?
C28 C27 C26 123.5(4) . . ?
C28 C27 H27 118.2 . . ?
C26 C27 H27 118.2 . . ?
C27 C28 C37 117.7(4) . . ?
C27 C28 C29 123.3(4) . . ?
C37 C28 C29 119.0(4) . . ?
C28 C29 C31 108.9(3) . . ?
C28 C29 C30 110.8(3) . . ?
C31 C29 C30 116.3(4) . . ?
C28 C29 H29 106.8 . . ?
C31 C29 H29 106.8 . . ?
C30 C29 H29 106.8 . . ?
C21 C30 C40 110.5(4) . . ?
C21 C30 C25 109.2(4) . . ?
C40 C30 C25 112.9(4) . . ?
C21 C30 C29 108.1(3) . . ?
C40 C30 C29 109.1(3) . . ?
C25 C30 C29 106.9(3) . . ?
C32 C31 C29 110.2(4) . . ?
C32 C31 H31A 109.6 . . ?
C29 C31 H31A 109.6 . . ?
C32 C31 H31B 109.6 . . ?
C29 C31 H31B 109.6 . . ?
H31A C31 H31B 108.1 . . ?
O5 C32 C31 111.1(3) . . ?
O5 C32 C33 105.1(3) . . ?
C31 C32 C33 115.7(4) . . ?
O5 C32 H32 108.2 . . ?
C31 C32 H32 108.2 . . ?
C33 C32 H32 108.2 . . ?
O6 C33 C34 107.2(4) . . ?
O6 C33 C36 110.9(4) . . ?
C34 C33 C36 109.1(4) . . ?
O6 C33 C32 109.7(3) . . ?
C34 C33 C32 109.1(3) . . ?
C36 C33 C32 110.7(4) . . ?
C35 C34 C33 126.1(5) . . ?
C35 C34 H34 116.9 . . ?
C33 C34 H34 116.9 . . ?
C34 C35 H35A 120.0 . . ?
C34 C35 H35B 120.0 . . ?
H35A C35 H35B 120.0 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O4 C37 O5 117.5(4) . . ?
O4 C37 C28 123.1(4) . . ?
O5 C37 C28 119.4(4) . . ?
C24 C38 H38A 109.5 . . ?
C24 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C24 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C24 C39 H39A 109.5 . . ?
C24 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C24 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C30 C40 H40A 109.5 . . ?
C30 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C30 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C17 O2 C12 122.7(3) . . ?
C13 O3 H3 109.5 . . ?
C37 O5 C32 122.8(3) . . ?
C33 O6 H6 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 -57.9(6) . . . . ?
C1 C2 C3 C4 59.0(6) . . . . ?
C2 C3 C4 C18 -170.7(4) . . . . ?
C2 C3 C4 C19 73.2(5) . . . . ?
C2 C3 C4 C5 -52.6(5) . . . . ?
C3 C4 C5 C6 179.2(4) . . . . ?
C18 C4 C5 C6 -63.2(5) . . . . ?
C19 C4 C5 C6 56.1(5) . . . . ?
C3 C4 C5 C10 47.6(5) . . . . ?
C18 C4 C5 C10 165.2(4) . . . . ?
C19 C4 C5 C10 -75.5(5) . . . . ?
C4 C5 C6 C7 -177.1(4) . . . . ?
C10 C5 C6 C7 -41.9(5) . . . . ?
C5 C6 C7 C8 8.8(7) . . . . ?
C6 C7 C8 C17 179.1(4) . . . . ?
C6 C7 C8 C9 0.5(7) . . . . ?
C7 C8 C9 C11 152.9(4) . . . . ?
C17 C8 C9 C11 -25.6(5) . . . . ?
C7 C8 C9 C10 23.6(6) . . . . ?
C17 C8 C9 C10 -154.9(4) . . . . ?
C2 C1 C10 C20 -74.5(5) . . . . ?
C2 C1 C10 C5 50.4(5) . . . . ?
C2 C1 C10 C9 165.0(4) . . . . ?
C6 C5 C10 C1 -179.8(3) . . . . ?
C4 C5 C10 C1 -46.8(5) . . . . ?
C6 C5 C10 C20 -56.7(5) . . . . ?
C4 C5 C10 C20 76.3(5) . . . . ?
C6 C5 C10 C9 64.0(4) . . . . ?
C4 C5 C10 C9 -163.0(4) . . . . ?
C8 C9 C10 C1 -170.5(4) . . . . ?
C11 C9 C10 C1 64.2(5) . . . . ?
C8 C9 C10 C20 68.8(4) . . . . ?
C11 C9 C10 C20 -56.5(5) . . . . ?
C8 C9 C10 C5 -54.1(4) . . . . ?
C11 C9 C10 C5 -179.4(3) . . . . ?
C8 C9 C11 C12 54.4(5) . . . . ?
C10 C9 C11 C12 -178.8(4) . . . . ?
C9 C11 C12 O2 -59.3(4) . . . . ?
C9 C11 C12 C13 -178.8(4) . . . . ?
O2 C12 C13 O3 -70.2(4) . . . . ?
C11 C12 C13 O3 51.7(5) . . . . ?
O2 C12 C13 C14 172.2(4) . . . . ?
C11 C12 C13 C14 -65.9(5) . . . . ?
O2 C12 C13 C16 52.6(5) . . . . ?
C11 C12 C13 C16 174.6(4) . . . . ?
O3 C13 C14 C15 19.5(7) . . . . ?
C16 C13 C14 C15 -101.2(6) . . . . ?
C12 C13 C14 C15 137.7(6) . . . . ?
C7 C8 C17 O1 0.0(7) . . . . ?
C9 C8 C17 O1 178.5(4) . . . . ?
C7 C8 C17 O2 -178.6(4) . . . . ?
C9 C8 C17 O2 -0.1(6) . . . . ?
C30 C21 C22 C23 -58.7(6) . . . . ?
C21 C22 C23 C24 58.4(6) . . . . ?
C22 C23 C24 C39 74.8(6) . . . . ?
C22 C23 C24 C38 -168.8(5) . . . . ?
C22 C23 C24 C25 -51.5(6) . . . . ?
C23 C24 C25 C26 178.5(4) . . . . ?
C39 C24 C25 C26 55.1(6) . . . . ?
C38 C24 C25 C26 -64.7(5) . . . . ?
C23 C24 C25 C30 46.9(6) . . . . ?
C39 C24 C25 C30 -76.5(5) . . . . ?
C38 C24 C25 C30 163.7(4) . . . . ?
C30 C25 C26 C27 -41.1(6) . . . . ?
C24 C25 C26 C27 -175.7(4) . . . . ?
C25 C26 C27 C28 8.4(8) . . . . ?
C26 C27 C28 C37 -179.7(4) . . . . ?
C26 C27 C28 C29 1.5(8) . . . . ?
C27 C28 C29 C31 150.8(5) . . . . ?
C37 C28 C29 C31 -28.0(5) . . . . ?
C27 C28 C29 C30 21.7(6) . . . . ?
C37 C28 C29 C30 -157.1(3) . . . . ?
C22 C21 C30 C40 -72.2(5) . . . . ?
C22 C21 C30 C25 52.5(6) . . . . ?
C22 C21 C30 C29 168.4(4) . . . . ?
C26 C25 C30 C21 179.3(4) . . . . ?
C24 C25 C30 C21 -47.8(5) . . . . ?
C26 C25 C30 C40 -57.3(5) . . . . ?
C24 C25 C30 C40 75.6(5) . . . . ?
C26 C25 C30 C29 62.7(5) . . . . ?
C24 C25 C30 C29 -164.4(4) . . . . ?
C28 C29 C30 C21 -169.1(4) . . . . ?
C31 C29 C30 C21 65.9(5) . . . . ?
C28 C29 C30 C40 70.7(5) . . . . ?
C31 C29 C30 C40 -54.3(5) . . . . ?
C28 C29 C30 C25 -51.6(4) . . . . ?
C31 C29 C30 C25 -176.7(3) . . . . ?
C28 C29 C31 C32 56.7(5) . . . . ?
C30 C29 C31 C32 -177.2(3) . . . . ?
C29 C31 C32 O5 -57.7(4) . . . . ?
C29 C31 C32 C33 -177.3(3) . . . . ?
O5 C32 C33 O6 -61.8(4) . . . . ?
C31 C32 C33 O6 61.1(5) . . . . ?
O5 C32 C33 C34 -179.0(4) . . . . ?
C31 C32 C33 C34 -56.1(5) . . . . ?
O5 C32 C33 C36 61.0(5) . . . . ?
C31 C32 C33 C36 -176.1(4) . . . . ?
O6 C33 C34 C35 6.5(7) . . . . ?
C36 C33 C34 C35 -113.7(6) . . . . ?
C32 C33 C34 C35 125.3(5) . . . . ?
C27 C28 C37 O4 1.1(7) . . . . ?
C29 C28 C37 O4 180.0(4) . . . . ?
C27 C28 C37 O5 179.8(4) . . . . ?
C29 C28 C37 O5 -1.4(6) . . . . ?
O1 C17 O2 C12 177.4(4) . . . . ?
C8 C17 O2 C12 -3.9(6) . . . . ?
C11 C12 O2 C17 33.9(5) . . . . ?
C13 C12 O2 C17 158.6(4) . . . . ?
O4 C37 O5 C32 -179.5(4) . . . . ?
C28 C37 O5 C32 1.8(6) . . . . ?
C31 C32 O5 C37 27.9(5) . . . . ?
C33 C32 O5 C37 153.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.57
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.038
