# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_151012a
_database_code_depnum_ccdc_archive 'CCDC 1454112'
_audit_update_record             
;
2016-02-17 deposited with the CCDC.
2016-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H26 O4'
_chemical_formula_weight         318.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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                   20.3794(7)
_cell_length_b                   9.1072(3)
_cell_length_c                   9.1422(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1696.79(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1903
_cell_measurement_theta_min      4.8500
_cell_measurement_theta_max      71.5780

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.47
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7231
_exptl_absorpt_correction_T_max  0.7364
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3560
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.34
_diffrn_reflns_theta_max         66.19
_reflns_number_total             2576
_reflns_number_gt                2365
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0516P)²+0.3424P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0147(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_number_reflns         2576
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1087
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.60323(13) 0.7688(2) -0.17470(18) 0.0681(6) Uani 1 1 d . . .
H1 H 0.5924 0.7280 -0.2509 0.102 Uiso 1 1 calc R . .
O2 O 0.55570(8) 0.60544(17) 0.60065(15) 0.0392(4) Uani 1 1 d . . .
H2 H 0.5200 0.6459 0.5909 0.059 Uiso 1 1 calc R . .
O3 O 0.56097(8) 0.2634(2) 0.6048(2) 0.0560(5) Uani 1 1 d . . .
O4 O 0.67309(11) -0.0269(2) 0.6721(3) 0.0713(6) Uani 1 1 d . . .
H4 H 0.6539 -0.0839 0.7268 0.107 Uiso 1 1 calc R . .
C1 C 0.67392(16) 0.4680(3) 0.0571(3) 0.0539(7) Uani 1 1 d . . .
H1A H 0.6529 0.3855 0.0091 0.065 Uiso 1 1 calc R . .
H1B H 0.7186 0.4397 0.0800 0.065 Uiso 1 1 calc R . .
C2 C 0.67497(16) 0.5987(3) -0.0469(3) 0.0595(8) Uani 1 1 d . . .
H2A H 0.7050 0.6727 -0.0104 0.071 Uiso 1 1 calc R . .
H2B H 0.6903 0.5673 -0.1424 0.071 Uiso 1 1 calc R . .
C3 C 0.60762(16) 0.6628(3) -0.0603(3) 0.0513(7) Uani 1 1 d . . .
H3 H 0.5774 0.5825 -0.0841 0.062 Uiso 1 1 calc R . .
C4 C 0.58406(13) 0.7327(3) 0.0827(3) 0.0458(6) Uani 1 1 d . . .
C5 C 0.59870(12) 0.6279(2) 0.2109(2) 0.0366(5) Uani 1 1 d . . .
C6 C 0.57130(11) 0.6613(2) 0.3466(2) 0.0375(5) Uani 1 1 d . . .
H6 H 0.5463 0.7461 0.3573 0.045 Uiso 1 1 calc R . .
C7 C 0.58070(11) 0.5705(2) 0.4647(2) 0.0334(5) Uani 1 1 d . . .
C8 C 0.61619(10) 0.4408(2) 0.4520(2) 0.0329(5) Uani 1 1 d . . .
C9 C 0.64454(11) 0.4065(2) 0.3172(2) 0.0351(5) Uani 1 1 d . . .
C10 C 0.63763(11) 0.5024(3) 0.1982(2) 0.0377(5) Uani 1 1 d . . .
C11 C 0.68289(13) 0.2654(3) 0.3003(3) 0.0465(6) Uani 1 1 d . . .
H11A H 0.7294 0.2885 0.2995 0.056 Uiso 1 1 calc R . .
H11B H 0.6721 0.2218 0.2065 0.056 Uiso 1 1 calc R . .
C12 C 0.66988(14) 0.1530(3) 0.4201(3) 0.0466(6) Uani 1 1 d . . .
H12A H 0.7018 0.0744 0.4126 0.056 Uiso 1 1 calc R . .
H12B H 0.6267 0.1107 0.4059 0.056 Uiso 1 1 calc R . .
C13 C 0.67368(11) 0.2206(3) 0.5728(3) 0.0397(5) Uani 1 1 d . . .
C14 C 0.62268(11) 0.3419(3) 0.5830(3) 0.0371(5) Uani 1 1 d . . .
H14 H 0.6318 0.4019 0.6697 0.045 Uiso 1 1 calc R . .
C15 C 0.57372(13) 0.1243(3) 0.6699(3) 0.0573(7) Uani 1 1 d . . .
H15A H 0.5583 0.0458 0.6070 0.069 Uiso 1 1 calc R . .
H15B H 0.5517 0.1165 0.7636 0.069 Uiso 1 1 calc R . .
C16 C 0.64707(13) 0.1151(3) 0.6895(3) 0.0477(6) Uani 1 1 d . . .
H16 H 0.6587 0.1523 0.7866 0.057 Uiso 1 1 calc R . .
C17 C 0.61871(17) 0.8811(3) 0.1068(3) 0.0620(8) Uani 1 1 d . . .
H17A H 0.6654 0.8664 0.1076 0.093 Uiso 1 1 calc R . .
H17B H 0.6051 0.9220 0.1987 0.093 Uiso 1 1 calc R . .
H17C H 0.6073 0.9472 0.0291 0.093 Uiso 1 1 calc R . .
C18 C 0.51010(16) 0.7594(4) 0.0720(3) 0.0714(9) Uani 1 1 d . . .
H18A H 0.5010 0.8209 -0.0109 0.107 Uiso 1 1 calc R . .
H18B H 0.4950 0.8068 0.1595 0.107 Uiso 1 1 calc R . .
H18C H 0.4879 0.6672 0.0605 0.107 Uiso 1 1 calc R . .
C19 C 0.74264(13) 0.2721(3) 0.6092(4) 0.0601(8) Uani 1 1 d . . .
H19A H 0.7566 0.3428 0.5378 0.090 Uiso 1 1 calc R . .
H19B H 0.7720 0.1897 0.6083 0.090 Uiso 1 1 calc R . .
H19C H 0.7429 0.3165 0.7044 0.090 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.426(3) . ?
O1 H1 0.8200 . ?
O2 C7 1.380(2) . ?
O2 H2 0.8200 . ?
O3 C15 1.423(3) . ?
O3 C14 1.460(3) . ?
O4 C16 1.407(3) . ?
O4 H4 0.8200 . ?
C1 C10 1.520(3) . ?
C1 C2 1.524(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.496(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.531(4) . ?
C3 H3 0.9800 . ?
C4 C18 1.530(4) . ?
C4 C5 1.540(3) . ?
C4 C17 1.540(3) . ?
C5 C6 1.394(3) . ?
C5 C10 1.396(3) . ?
C6 C7 1.373(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.390(3) . ?
C8 C9 1.397(3) . ?
C8 C14 1.505(3) . ?
C9 C10 1.402(3) . ?
C9 C11 1.511(3) . ?
C11 C12 1.523(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.528(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C19 1.518(3) . ?
C13 C14 1.519(3) . ?
C13 C16 1.535(3) . ?
C14 H14 0.9800 . ?
C15 C16 1.508(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 109.5 . . ?
C7 O2 H2 109.5 . . ?
C15 O3 C14 109.58(18) . . ?
C16 O4 H4 109.5 . . ?
C10 C1 C2 112.1(2) . . ?
C10 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
C10 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C3 C2 C1 110.1(2) . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.2 . . ?
O1 C3 C2 112.4(2) . . ?
O1 C3 C4 109.0(2) . . ?
C2 C3 C4 112.3(2) . . ?
O1 C3 H3 107.6 . . ?
C2 C3 H3 107.6 . . ?
C4 C3 H3 107.6 . . ?
C18 C4 C3 108.7(2) . . ?
C18 C4 C5 109.8(2) . . ?
C3 C4 C5 109.4(2) . . ?
C18 C4 C17 108.7(3) . . ?
C3 C4 C17 110.0(2) . . ?
C5 C4 C17 110.25(19) . . ?
C6 C5 C10 118.66(19) . . ?
C6 C5 C4 117.7(2) . . ?
C10 C5 C4 123.7(2) . . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 O2 121.19(19) . . ?
C6 C7 C8 121.20(19) . . ?
O2 C7 C8 117.61(19) . . ?
C7 C8 C9 118.66(19) . . ?
C7 C8 C14 119.19(19) . . ?
C9 C8 C14 122.15(19) . . ?
C8 C9 C10 120.22(19) . . ?
C8 C9 C11 119.6(2) . . ?
C10 C9 C11 120.1(2) . . ?
C5 C10 C9 120.20(19) . . ?
C5 C10 C1 121.0(2) . . ?
C9 C10 C1 118.7(2) . . ?
C9 C11 C12 114.07(19) . . ?
C9 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C9 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 C13 112.17(19) . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C19 C13 C14 113.3(2) . . ?
C19 C13 C12 111.8(2) . . ?
C14 C13 C12 108.3(2) . . ?
C19 C13 C16 111.6(2) . . ?
C14 C13 C16 99.82(19) . . ?
C12 C13 C16 111.4(2) . . ?
O3 C14 C8 109.02(18) . . ?
O3 C14 C13 104.01(18) . . ?
C8 C14 C13 116.50(19) . . ?
O3 C14 H14 109.0 . . ?
C8 C14 H14 109.0 . . ?
C13 C14 H14 109.0 . . ?
O3 C15 C16 106.3(2) . . ?
O3 C15 H15A 110.5 . . ?
C16 C15 H15A 110.5 . . ?
O3 C15 H15B 110.5 . . ?
C16 C15 H15B 110.5 . . ?
H15A C15 H15B 108.7 . . ?
O4 C16 C15 114.3(2) . . ?
O4 C16 C13 111.4(2) . . ?
C15 C16 C13 103.5(2) . . ?
O4 C16 H16 109.2 . . ?
C15 C16 H16 109.2 . . ?
C13 C16 H16 109.2 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 -47.7(3) . . . . ?
C1 C2 C3 O1 -169.9(2) . . . . ?
C1 C2 C3 C4 66.7(3) . . . . ?
O1 C3 C4 C18 69.0(3) . . . . ?
C2 C3 C4 C18 -165.7(2) . . . . ?
O1 C3 C4 C5 -171.2(2) . . . . ?
C2 C3 C4 C5 -45.9(3) . . . . ?
O1 C3 C4 C17 -49.9(3) . . . . ?
C2 C3 C4 C17 75.3(3) . . . . ?
C18 C4 C5 C6 -50.6(3) . . . . ?
C3 C4 C5 C6 -169.7(2) . . . . ?
C17 C4 C5 C6 69.2(3) . . . . ?
C18 C4 C5 C10 129.4(3) . . . . ?
C3 C4 C5 C10 10.3(3) . . . . ?
C17 C4 C5 C10 -110.8(3) . . . . ?
C10 C5 C6 C7 -1.9(3) . . . . ?
C4 C5 C6 C7 178.1(2) . . . . ?
C5 C6 C7 O2 177.7(2) . . . . ?
C5 C6 C7 C8 -1.8(3) . . . . ?
C6 C7 C8 C9 2.4(3) . . . . ?
O2 C7 C8 C9 -177.09(19) . . . . ?
C6 C7 C8 C14 -177.4(2) . . . . ?
O2 C7 C8 C14 3.1(3) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C14 C8 C9 C10 -179.5(2) . . . . ?
C7 C8 C9 C11 -179.5(2) . . . . ?
C14 C8 C9 C11 0.3(3) . . . . ?
C6 C5 C10 C9 4.9(3) . . . . ?
C4 C5 C10 C9 -175.1(2) . . . . ?
C6 C5 C10 C1 -174.3(2) . . . . ?
C4 C5 C10 C1 5.8(3) . . . . ?
C8 C9 C10 C5 -4.3(3) . . . . ?
C11 C9 C10 C5 175.8(2) . . . . ?
C8 C9 C10 C1 174.8(2) . . . . ?
C11 C9 C10 C1 -5.0(3) . . . . ?
C2 C1 C10 C5 13.0(4) . . . . ?
C2 C1 C10 C9 -166.1(2) . . . . ?
C8 C9 C11 C12 17.3(3) . . . . ?
C10 C9 C11 C12 -162.9(2) . . . . ?
C9 C11 C12 C13 -48.2(3) . . . . ?
C11 C12 C13 C19 -65.9(3) . . . . ?
C11 C12 C13 C14 59.7(3) . . . . ?
C11 C12 C13 C16 168.5(2) . . . . ?
C15 O3 C14 C8 150.1(2) . . . . ?
C15 O3 C14 C13 25.2(3) . . . . ?
C7 C8 C14 O3 75.8(2) . . . . ?
C9 C8 C14 O3 -104.0(2) . . . . ?
C7 C8 C14 C13 -167.0(2) . . . . ?
C9 C8 C14 C13 13.3(3) . . . . ?
C19 C13 C14 O3 -157.4(2) . . . . ?
C12 C13 C14 O3 77.9(2) . . . . ?
C16 C13 C14 O3 -38.6(2) . . . . ?
C19 C13 C14 C8 82.6(3) . . . . ?
C12 C13 C14 C8 -42.0(3) . . . . ?
C16 C13 C14 C8 -158.6(2) . . . . ?
C14 O3 C15 C16 -0.1(3) . . . . ?
O3 C15 C16 O4 -145.9(2) . . . . ?
O3 C15 C16 C13 -24.7(3) . . . . ?
C19 C13 C16 O4 -78.4(3) . . . . ?
C14 C13 C16 O4 161.6(2) . . . . ?
C12 C13 C16 O4 47.4(3) . . . . ?
C19 C13 C16 C15 158.4(2) . . . . ?
C14 C13 C16 C15 38.4(3) . . . . ?
C12 C13 C16 C15 -75.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        66.19
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.037
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_150503g
_database_code_depnum_ccdc_archive 'CCDC 1454113'
_audit_update_record             
;
2016-02-17 deposited with the CCDC.
2016-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H28 O4'
_chemical_formula_weight         320.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   6.2051(6)
_cell_length_b                   8.2010(8)
_cell_length_c                   34.011(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1730.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    876
_cell_measurement_theta_min      5.5480
_cell_measurement_theta_max      69.6310

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.7632
_exptl_absorpt_correction_T_max  0.8430
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3516
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0665
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         65.90
_reflns_number_total             2511
_reflns_number_gt                1809
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0597P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0036(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(5)
_refine_ls_number_reflns         2511
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1522
_refine_ls_wR_factor_gt          0.1321
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2515(5) 0.5684(3) 0.04658(9) 0.0617(9) Uani 1 1 d . . .
O2 O -0.0100(5) 0.1850(4) 0.05197(14) 0.0815(11) Uani 1 1 d . . .
H2 H 0.0289 0.0894 0.0520 0.122 Uiso 1 1 calc R . .
O3 O 0.6734(5) 0.7429(3) 0.04715(6) 0.0519(8) Uani 1 1 d . . .
H3 H 0.7539 0.8211 0.0440 0.078 Uiso 1 1 calc R . .
O4 O 0.0715(5) 0.8644(3) 0.02964(7) 0.0558(9) Uani 1 1 d . . .
H4C H 0.1207 0.7791 0.0406 0.067 Uiso 1 1 d R . .
H4D H 0.0884 0.8541 0.0050 0.067 Uiso 1 1 d R . .
C1 C 0.0919(8) 0.4573(5) 0.03348(15) 0.0683(15) Uani 1 1 d . . .
H1A H 0.0735 0.4659 0.0052 0.082 Uiso 1 1 calc R . .
H1B H -0.0451 0.4807 0.0460 0.082 Uiso 1 1 calc R . .
C2 C 0.1684(7) 0.2865(5) 0.04448(13) 0.0552(11) Uani 1 1 d . . .
H2A H 0.2519 0.2410 0.0226 0.066 Uiso 1 1 calc R . .
C3 C 0.3197(7) 0.3184(5) 0.07934(12) 0.0465(10) Uani 1 1 d . . .
C4 C 0.4223(7) 0.4775(4) 0.06589(11) 0.0439(10) Uani 1 1 d . . .
H4 H 0.5328 0.4517 0.0462 0.053 Uiso 1 1 calc R . .
C5 C 0.5251(7) 0.5791(5) 0.09771(11) 0.0404(9) Uani 1 1 d . . .
C6 C 0.5012(7) 0.5436(5) 0.13769(12) 0.0460(10) Uani 1 1 d . . .
C7 C 0.3448(8) 0.4097(5) 0.15013(12) 0.0611(13) Uani 1 1 d . . .
H7A H 0.4272 0.3175 0.1598 0.073 Uiso 1 1 calc R . .
H7B H 0.2578 0.4499 0.1718 0.073 Uiso 1 1 calc R . .
C8 C 0.1951(7) 0.3507(5) 0.11761(13) 0.0576(12) Uani 1 1 d . . .
H8A H 0.0850 0.4323 0.1128 0.069 Uiso 1 1 calc R . .
H8B H 0.1240 0.2512 0.1260 0.069 Uiso 1 1 calc R . .
C9 C 0.6578(7) 0.7074(4) 0.08688(10) 0.0416(9) Uani 1 1 d . . .
C10 C 0.7699(7) 0.7976(5) 0.11446(11) 0.0459(10) Uani 1 1 d . . .
H10 H 0.8550 0.8848 0.1064 0.055 Uiso 1 1 calc R . .
C11 C 0.7560(7) 0.7589(5) 0.15423(10) 0.0428(9) Uani 1 1 d . . .
C12 C 0.6195(7) 0.6330(5) 0.16594(11) 0.0465(10) Uani 1 1 d . . .
C13 C 0.5967(9) 0.5858(6) 0.20924(11) 0.0656(14) Uani 1 1 d . . .
H13A H 0.4453 0.5700 0.2152 0.079 Uiso 1 1 calc R . .
H13B H 0.6700 0.4830 0.2136 0.079 Uiso 1 1 calc R . .
C14 C 0.6870(11) 0.7109(7) 0.23655(13) 0.091(2) Uani 1 1 d . . .
H14A H 0.5833 0.7986 0.2393 0.110 Uiso 1 1 calc R . .
H14B H 0.7064 0.6617 0.2622 0.110 Uiso 1 1 calc R . .
C15 C 0.8911(10) 0.7795(8) 0.22385(13) 0.0888(19) Uani 1 1 d . . .
H15A H 0.9979 0.6932 0.2234 0.107 Uiso 1 1 calc R . .
H15B H 0.9373 0.8593 0.2431 0.107 Uiso 1 1 calc R . .
C16 C 0.8858(7) 0.8611(6) 0.18340(11) 0.0531(11) Uani 1 1 d . . .
C17 C 0.7887(10) 1.0326(5) 0.18594(14) 0.0776(17) Uani 1 1 d . . .
H17A H 0.6375 1.0246 0.1916 0.116 Uiso 1 1 calc R . .
H17B H 0.8087 1.0878 0.1613 0.116 Uiso 1 1 calc R . .
H17C H 0.8591 1.0926 0.2065 0.116 Uiso 1 1 calc R . .
C18 C 0.4813(8) 0.1807(5) 0.08456(14) 0.0613(13) Uani 1 1 d . . .
H18A H 0.5506 0.1586 0.0599 0.092 Uiso 1 1 calc R . .
H18B H 0.4078 0.0845 0.0935 0.092 Uiso 1 1 calc R . .
H18C H 0.5876 0.2120 0.1036 0.092 Uiso 1 1 calc R . .
C19 C 1.1209(8) 0.8788(7) 0.16927(15) 0.0779(16) Uani 1 1 d . . .
H19A H 1.2052 0.9298 0.1895 0.117 Uiso 1 1 calc R . .
H19B H 1.1247 0.9447 0.1460 0.117 Uiso 1 1 calc R . .
H19C H 1.1791 0.7730 0.1636 0.117 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.418(5) . ?
O1 C4 1.453(5) . ?
O2 C2 1.409(5) . ?
O2 H2 0.8200 . ?
O3 C9 1.386(4) . ?
O3 H3 0.8200 . ?
O4 H4C 0.8501 . ?
O4 H4D 0.8499 . ?
C1 C2 1.526(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.534(5) . ?
C2 H2A 0.9800 . ?
C3 C18 1.521(5) . ?
C3 C4 1.522(5) . ?
C3 C8 1.537(5) . ?
C4 C5 1.508(5) . ?
C4 H4 0.9800 . ?
C5 C9 1.386(5) . ?
C5 C6 1.398(5) . ?
C6 C12 1.414(5) . ?
C6 C7 1.526(6) . ?
C7 C8 1.523(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.382(5) . ?
C10 C11 1.392(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.393(5) . ?
C11 C16 1.528(5) . ?
C12 C13 1.529(5) . ?
C13 C14 1.493(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.451(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.530(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.532(6) . ?
C16 C19 1.543(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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 C4 108.7(3) . . ?
C2 O2 H2 109.5 . . ?
C9 O3 H3 109.5 . . ?
H4C O4 H4D 107.9 . . ?
O1 C1 C2 107.2(4) . . ?
O1 C1 H1A 110.3 . . ?
C2 C1 H1A 110.3 . . ?
O1 C1 H1B 110.3 . . ?
C2 C1 H1B 110.3 . . ?
H1A C1 H1B 108.5 . . ?
O2 C2 C1 110.0(4) . . ?
O2 C2 C3 116.2(4) . . ?
C1 C2 C3 102.9(3) . . ?
O2 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C18 C3 C4 113.3(3) . . ?
C18 C3 C2 111.5(3) . . ?
C4 C3 C2 99.8(3) . . ?
C18 C3 C8 111.1(4) . . ?
C4 C3 C8 108.5(3) . . ?
C2 C3 C8 112.1(3) . . ?
O1 C4 C5 110.4(3) . . ?
O1 C4 C3 105.7(3) . . ?
C5 C4 C3 115.8(3) . . ?
O1 C4 H4 108.2 . . ?
C5 C4 H4 108.2 . . ?
C3 C4 H4 108.2 . . ?
C9 C5 C6 118.7(4) . . ?
C9 C5 C4 118.7(3) . . ?
C6 C5 C4 122.5(4) . . ?
C5 C6 C12 119.8(4) . . ?
C5 C6 C7 119.2(4) . . ?
C12 C6 C7 121.0(3) . . ?
C8 C7 C6 114.5(3) . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 C3 111.3(3) . . ?
C7 C8 H8A 109.4 . . ?
C3 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C3 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 O3 121.0(3) . . ?
C10 C9 C5 121.7(3) . . ?
O3 C9 C5 117.4(3) . . ?
C9 C10 C11 120.4(4) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 119.0(4) . . ?
C10 C11 C16 118.2(4) . . ?
C12 C11 C16 122.8(3) . . ?
C11 C12 C6 120.4(3) . . ?
C11 C12 C13 121.3(4) . . ?
C6 C12 C13 118.4(4) . . ?
C14 C13 C12 113.0(4) . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C13 114.1(5) . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C13 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 C16 114.7(4) . . ?
C14 C15 H15A 108.6 . . ?
C16 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
C16 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C11 C16 C15 110.8(4) . . ?
C11 C16 C17 109.4(4) . . ?
C15 C16 C17 111.0(4) . . ?
C11 C16 C19 110.4(4) . . ?
C15 C16 C19 107.5(4) . . ?
C17 C16 C19 107.6(4) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C4 O1 C1 C2 -1.1(5) . . . . ?
O1 C1 C2 O2 149.2(4) . . . . ?
O1 C1 C2 C3 24.7(5) . . . . ?
O2 C2 C3 C18 82.9(4) . . . . ?
C1 C2 C3 C18 -156.9(4) . . . . ?
O2 C2 C3 C4 -157.2(3) . . . . ?
C1 C2 C3 C4 -36.9(4) . . . . ?
O2 C2 C3 C8 -42.5(5) . . . . ?
C1 C2 C3 C8 77.8(4) . . . . ?
C1 O1 C4 C5 -149.5(4) . . . . ?
C1 O1 C4 C3 -23.5(5) . . . . ?
C18 C3 C4 O1 156.1(4) . . . . ?
C2 C3 C4 O1 37.4(4) . . . . ?
C8 C3 C4 O1 -80.0(4) . . . . ?
C18 C3 C4 C5 -81.4(5) . . . . ?
C2 C3 C4 C5 160.0(3) . . . . ?
C8 C3 C4 C5 42.6(5) . . . . ?
O1 C4 C5 C9 -72.7(5) . . . . ?
C3 C4 C5 C9 167.2(3) . . . . ?
O1 C4 C5 C6 110.9(4) . . . . ?
C3 C4 C5 C6 -9.2(6) . . . . ?
C9 C5 C6 C12 -3.0(6) . . . . ?
C4 C5 C6 C12 173.4(4) . . . . ?
C9 C5 C6 C7 176.2(4) . . . . ?
C4 C5 C6 C7 -7.4(6) . . . . ?
C5 C6 C7 C8 -11.8(6) . . . . ?
C12 C6 C7 C8 167.3(4) . . . . ?
C6 C7 C8 C3 46.7(5) . . . . ?
C18 C3 C8 C7 63.9(4) . . . . ?
C4 C3 C8 C7 -61.3(5) . . . . ?
C2 C3 C8 C7 -170.5(3) . . . . ?
C6 C5 C9 C10 1.5(6) . . . . ?
C4 C5 C9 C10 -175.0(4) . . . . ?
C6 C5 C9 O3 -178.1(4) . . . . ?
C4 C5 C9 O3 5.3(6) . . . . ?
O3 C9 C10 C11 -178.8(4) . . . . ?
C5 C9 C10 C11 1.6(6) . . . . ?
C9 C10 C11 C12 -3.1(6) . . . . ?
C9 C10 C11 C16 179.1(4) . . . . ?
C10 C11 C12 C6 1.6(6) . . . . ?
C16 C11 C12 C6 179.3(4) . . . . ?
C10 C11 C12 C13 -179.6(4) . . . . ?
C16 C11 C12 C13 -1.9(6) . . . . ?
C5 C6 C12 C11 1.5(6) . . . . ?
C7 C6 C12 C11 -177.7(4) . . . . ?
C5 C6 C12 C13 -177.4(4) . . . . ?
C7 C6 C12 C13 3.5(6) . . . . ?
C11 C12 C13 C14 14.5(7) . . . . ?
C6 C12 C13 C14 -166.7(5) . . . . ?
C12 C13 C14 C15 -42.0(7) . . . . ?
C13 C14 C15 C16 58.1(7) . . . . ?
C10 C11 C16 C15 -167.5(4) . . . . ?
C12 C11 C16 C15 14.8(6) . . . . ?
C10 C11 C16 C17 69.7(5) . . . . ?
C12 C11 C16 C17 -108.0(5) . . . . ?
C10 C11 C16 C19 -48.5(5) . . . . ?
C12 C11 C16 C19 133.8(4) . . . . ?
C14 C15 C16 C11 -42.3(7) . . . . ?
C14 C15 C16 C17 79.5(6) . . . . ?
C14 C15 C16 C19 -163.0(5) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        65.90
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.040
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_150503e
_database_code_depnum_ccdc_archive 'CCDC 1454114'
_audit_update_record             
;
2016-02-17 deposited with the CCDC.
2016-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'asperether C'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H26 O4'
_chemical_formula_weight         318.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   11.1182(10)
_cell_length_b                   12.8745(11)
_cell_length_c                   11.7116(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.3980(10)
_cell_angle_gamma                90.00
_cell_volume                     1676.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    434
_cell_measurement_theta_min      4.0550
_cell_measurement_theta_max      68.7030

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.7913
_exptl_absorpt_correction_T_max  0.9331
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5644
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_sigmaI/netI    0.1187
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.77
_diffrn_reflns_theta_max         65.94
_reflns_number_total             3793
_reflns_number_gt                2423
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0320P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0096(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(4)
_refine_ls_number_reflns         3793
_refine_ls_number_parameters     455
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1375
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0519(4) 0.4342(4) 0.2456(3) 0.0453(12) Uani 1 1 d . . .
O2 O 0.2700(6) 0.4703(4) 0.0264(4) 0.0684(17) Uani 1 1 d . . .
H2 H 0.2775 0.5211 -0.0152 0.103 Uiso 1 1 calc R . .
O3 O -0.0012(4) 0.4923(4) 0.4934(4) 0.0481(13) Uani 1 1 d . . .
H3 H -0.0378 0.5017 0.5531 0.072 Uiso 1 1 calc R . .
O4 O 0.2707(5) 0.2751(4) 0.9295(4) 0.0549(14) Uani 1 1 d . . .
H4 H 0.2692 0.3235 0.9750 0.082 Uiso 1 1 calc R . .
O5 O 0.7524(4) 0.1561(4) 0.0736(4) 0.0448(12) Uani 1 1 d . . .
O6 O 0.9859(4) 0.2319(4) 0.2675(5) 0.0540(14) Uani 1 1 d . . .
H6 H 1.0134 0.2891 0.2840 0.081 Uiso 1 1 calc R . .
O7 O 0.4904(4) 0.2072(4) 0.0112(4) 0.0493(13) Uani 1 1 d . . .
H7 H 0.4245 0.2199 -0.0175 0.074 Uiso 1 1 calc R . .
O8 O 0.1240(4) 0.0579(4) 0.3095(4) 0.0503(13) Uani 1 1 d . . .
H8 H 0.0852 0.1111 0.2983 0.075 Uiso 1 1 calc R . .
C1 C 0.0803(6) 0.4527(6) 0.1276(5) 0.0482(18) Uani 1 1 d . . .
H1A H 0.0227 0.5005 0.0939 0.058 Uiso 1 1 calc R . .
H1B H 0.0780 0.3882 0.0850 0.058 Uiso 1 1 calc R . .
C2 C 0.2050(6) 0.4987(6) 0.1249(5) 0.0476(19) Uani 1 1 d . . .
H2A H 0.1994 0.5746 0.1290 0.057 Uiso 1 1 calc R . .
C3 C 0.2622(6) 0.4576(6) 0.2350(5) 0.0433(17) Uani 1 1 d . . .
C4 C 0.1560(5) 0.4620(5) 0.3160(5) 0.0349(15) Uani 1 1 d . . .
H4A H 0.1461 0.5341 0.3411 0.042 Uiso 1 1 calc R . .
C5 C 0.1614(5) 0.3945(5) 0.4196(5) 0.0331(15) Uani 1 1 d . . .
C6 C 0.2422(6) 0.3139(5) 0.4314(5) 0.0352(15) Uani 1 1 d . . .
C7 C 0.3310(6) 0.2909(6) 0.3357(5) 0.0452(18) Uani 1 1 d . . .
H7A H 0.3344 0.2163 0.3239 0.054 Uiso 1 1 calc R . .
H7B H 0.4105 0.3136 0.3595 0.054 Uiso 1 1 calc R . .
C8 C 0.2987(6) 0.3435(5) 0.2224(5) 0.0434(18) Uani 1 1 d . . .
H8A H 0.3673 0.3393 0.1719 0.052 Uiso 1 1 calc R . .
H8B H 0.2329 0.3057 0.1868 0.052 Uiso 1 1 calc R . .
C9 C 0.0824(5) 0.4148(5) 0.5090(5) 0.0365(16) Uani 1 1 d . . .
C10 C 0.0908(6) 0.3582(5) 0.6108(5) 0.0361(16) Uani 1 1 d . . .
H10 H 0.0389 0.3726 0.6707 0.043 Uiso 1 1 calc R . .
C11 C 0.1769(6) 0.2805(5) 0.6224(5) 0.0369(16) Uani 1 1 d . A .
C12 C 0.2511(5) 0.2544(5) 0.5317(5) 0.0373(16) Uani 1 1 d . A .
C13 C 0.3347(6) 0.1615(6) 0.5361(5) 0.0445(18) Uani 1 1 d . . .
H13A H 0.3298 0.1248 0.4639 0.053 Uiso 0.57(3) 1 calc PR A 1
H13B H 0.4167 0.1860 0.5455 0.053 Uiso 0.57(3) 1 calc PR A 1
H13C H 0.4128 0.1806 0.5062 0.053 Uiso 0.43(3) 1 d PR A 2
H13D H 0.3023 0.1063 0.4887 0.053 Uiso 0.43(3) 1 d PR A 2
C14 C 0.307(2) 0.0883(17) 0.6295(18) 0.045(5) Uani 0.57(3) 1 d P A 1
H14A H 0.3683 0.0348 0.6342 0.054 Uiso 0.57(3) 1 calc PR A 1
H14B H 0.2299 0.0552 0.6156 0.054 Uiso 0.57(3) 1 calc PR A 1
C15 C 0.303(2) 0.1506(15) 0.7416(12) 0.043(5) Uani 0.57(3) 1 d P A 1
H15A H 0.3778 0.1892 0.7507 0.052 Uiso 0.57(3) 1 calc PR A 1
H15B H 0.2965 0.1032 0.8056 0.052 Uiso 0.57(3) 1 calc PR A 1
C14' C 0.349(3) 0.120(2) 0.663(2) 0.047(6) Uani 0.43(3) 1 d P A 2
H14C H 0.3792 0.0491 0.6610 0.056 Uiso 0.43(3) 1 calc PR A 2
H14D H 0.4082 0.1619 0.7030 0.056 Uiso 0.43(3) 1 calc PR A 2
C15' C 0.235(3) 0.1210(19) 0.7299(17) 0.044(6) Uani 0.43(3) 1 d P A 2
H15C H 0.1744 0.0793 0.6911 0.053 Uiso 0.43(3) 1 calc PR A 2
H15D H 0.2488 0.0914 0.8050 0.053 Uiso 0.43(3) 1 calc PR A 2
C16 C 0.1915(6) 0.2297(6) 0.7413(6) 0.0439(18) Uani 1 1 d . . .
C17 C 0.2476(6) 0.3135(6) 0.8162(5) 0.050(2) Uani 1 1 d . A .
H17A H 0.3225 0.3367 0.7826 0.060 Uiso 1 1 calc R . .
H17B H 0.1938 0.3727 0.8201 0.060 Uiso 1 1 calc R . .
C18 C 0.3684(7) 0.5233(6) 0.2767(6) 0.065(2) Uani 1 1 d . . .
H18A H 0.3414 0.5927 0.2923 0.097 Uiso 1 1 calc R . .
H18B H 0.4291 0.5252 0.2188 0.097 Uiso 1 1 calc R . .
H18C H 0.4014 0.4934 0.3451 0.097 Uiso 1 1 calc R . .
C19 C 0.083(2) 0.1775(18) 0.783(2) 0.050(5) Uani 0.57(3) 1 d P A 1
H19A H 0.0697 0.1147 0.7407 0.075 Uiso 0.57(3) 1 calc PR A 1
H19B H 0.0148 0.2227 0.7738 0.075 Uiso 0.57(3) 1 calc PR A 1
H19C H 0.0930 0.1611 0.8627 0.075 Uiso 0.57(3) 1 calc PR A 1
C19' C 0.059(3) 0.221(2) 0.801(3) 0.050(7) Uani 0.43(3) 1 d P A 2
H19D H 0.0043 0.1869 0.7499 0.075 Uiso 0.43(3) 1 calc PR A 2
H19E H 0.0300 0.2894 0.8182 0.075 Uiso 0.43(3) 1 calc PR A 2
H19F H 0.0661 0.1816 0.8705 0.075 Uiso 0.43(3) 1 calc PR A 2
C20 C 0.8756(6) 0.1768(6) 0.0987(5) 0.0445(18) Uani 1 1 d . . .
H20A H 0.9131 0.2125 0.0352 0.053 Uiso 1 1 calc R . .
H20B H 0.9187 0.1125 0.1126 0.053 Uiso 1 1 calc R . .
C21 C 0.8778(6) 0.2446(6) 0.2045(5) 0.0425(17) Uani 1 1 d . . .
H21 H 0.8719 0.3174 0.1805 0.051 Uiso 1 1 calc R . .
C22 C 0.7627(6) 0.2154(5) 0.2647(5) 0.0364(16) Uani 1 1 d . . .
C23 C 0.6785(5) 0.2011(5) 0.1637(5) 0.0363(16) Uani 1 1 d . . .
H23 H 0.6511 0.2698 0.1384 0.044 Uiso 1 1 calc R . .
C24 C 0.5706(5) 0.1337(5) 0.1810(5) 0.0350(15) Uani 1 1 d . . .
C25 C 0.5607(5) 0.0629(5) 0.2716(5) 0.0369(16) Uani 1 1 d . . .
C26 C 0.6593(5) 0.0620(6) 0.3626(5) 0.0426(17) Uani 1 1 d . . .
H26A H 0.6739 -0.0093 0.3855 0.051 Uiso 1 1 calc R . .
H26B H 0.6306 0.0992 0.4290 0.051 Uiso 1 1 calc R . .
C27 C 0.7784(6) 0.1100(5) 0.3257(6) 0.0443(18) Uani 1 1 d . . .
H27A H 0.8189 0.0622 0.2747 0.053 Uiso 1 1 calc R . .
H27B H 0.8293 0.1195 0.3924 0.053 Uiso 1 1 calc R . .
C28 C 0.4764(6) 0.1389(6) 0.0997(5) 0.0381(16) Uani 1 1 d . . .
C29 C 0.3757(6) 0.0786(5) 0.1122(5) 0.0398(17) Uani 1 1 d . . .
H29 H 0.3125 0.0856 0.0604 0.048 Uiso 1 1 calc R . .
C30 C 0.3660(5) 0.0062(5) 0.2021(5) 0.0357(15) Uani 1 1 d . . .
C31 C 0.4612(5) -0.0016(5) 0.2809(5) 0.0367(16) Uani 1 1 d . . .
C32 C 0.4574(6) -0.0851(5) 0.3722(5) 0.0409(17) Uani 1 1 d . . .
H32A H 0.5382 -0.1114 0.3850 0.049 Uiso 1 1 calc R . .
H32B H 0.4300 -0.0545 0.4431 0.049 Uiso 1 1 calc R . .
C33 C 0.3757(6) -0.1744(6) 0.3408(6) 0.0500(19) Uani 1 1 d . . .
H33A H 0.3702 -0.2225 0.4043 0.060 Uiso 1 1 calc R . .
H33B H 0.4082 -0.2115 0.2758 0.060 Uiso 1 1 calc R . .
C34 C 0.2520(6) -0.1327(6) 0.3114(6) 0.0464(18) Uani 1 1 d . . .
H34A H 0.2213 -0.0942 0.3761 0.056 Uiso 1 1 calc R . .
H34B H 0.1979 -0.1905 0.2971 0.056 Uiso 1 1 calc R . .
C35 C 0.2535(6) -0.0616(6) 0.2060(5) 0.0431(18) Uani 1 1 d . . .
C36 C 0.1393(6) 0.0039(6) 0.2039(5) 0.0457(19) Uani 1 1 d . . .
H36A H 0.1436 0.0538 0.1419 0.055 Uiso 1 1 calc R . .
H36B H 0.0704 -0.0406 0.1901 0.055 Uiso 1 1 calc R . .
C37 C 0.7226(6) 0.2986(6) 0.3464(6) 0.059(2) Uani 1 1 d . . .
H37A H 0.7141 0.3632 0.3061 0.088 Uiso 1 1 calc R . .
H37B H 0.7814 0.3063 0.4061 0.088 Uiso 1 1 calc R . .
H37C H 0.6467 0.2795 0.3789 0.088 Uiso 1 1 calc R . .
C38 C 0.2494(7) -0.1276(6) 0.0963(6) 0.065(2) Uani 1 1 d . . .
H38A H 0.3201 -0.1702 0.0925 0.097 Uiso 1 1 calc R . .
H38B H 0.2461 -0.0827 0.0309 0.097 Uiso 1 1 calc R . .
H38C H 0.1793 -0.1712 0.0971 0.097 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.439(6) . ?
O1 C4 1.461(6) . ?
O2 C2 1.414(7) . ?
O2 H2 0.8200 . ?
O3 C9 1.375(7) . ?
O3 H3 0.8200 . ?
O4 C17 1.437(7) . ?
O4 H4 0.8200 . ?
O5 C20 1.423(7) . ?
O5 C23 1.461(7) . ?
O6 C21 1.415(7) . ?
O6 H6 0.8200 . ?
O7 C28 1.369(7) . ?
O7 H7 0.8200 . ?
O8 C36 1.430(7) . ?
O8 H8 0.8200 . ?
C1 C2 1.508(8) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.528(8) . ?
C2 H2A 0.9800 . ?
C3 C4 1.521(8) . ?
C3 C18 1.531(9) . ?
C3 C8 1.531(9) . ?
C4 C5 1.494(8) . ?
C4 H4A 0.9800 . ?
C5 C6 1.379(8) . ?
C5 C9 1.396(8) . ?
C6 C12 1.405(8) . ?
C6 C7 1.528(7) . ?
C7 C8 1.531(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.400(8) . ?
C10 C11 1.390(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(8) . ?
C11 C16 1.546(8) . ?
C12 C13 1.515(9) . ?
C13 C14 1.48(2) . ?
C13 C14' 1.59(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C13 H13D 0.9700 . ?
C14 C15 1.54(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.608(18) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C14' C15' 1.49(4) . ?
C14' H14C 0.9700 . ?
C14' H14D 0.9700 . ?
C15' C16 1.49(2) . ?
C15' H15C 0.9700 . ?
C15' H15D 0.9700 . ?
C16 C19 1.47(3) . ?
C16 C17 1.522(9) . ?
C16 C19' 1.64(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C19' H19D 0.9600 . ?
C19' H19E 0.9600 . ?
C19' H19F 0.9600 . ?
C20 C21 1.516(8) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.514(8) . ?
C21 H21 0.9800 . ?
C22 C37 1.506(8) . ?
C22 C23 1.515(8) . ?
C22 C27 1.543(8) . ?
C23 C24 1.496(8) . ?
C23 H23 0.9800 . ?
C24 C25 1.404(8) . ?
C24 C28 1.412(8) . ?
C25 C31 1.388(8) . ?
C25 C26 1.524(7) . ?
C26 C27 1.526(8) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.371(8) . ?
C29 C30 1.410(8) . ?
C29 H29 0.9300 . ?
C30 C31 1.403(8) . ?
C30 C35 1.526(8) . ?
C31 C32 1.517(8) . ?
C32 C33 1.510(8) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.514(8) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.537(9) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.525(8) . ?
C35 C38 1.541(9) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C4 108.8(4) . . ?
C2 O2 H2 109.5 . . ?
C9 O3 H3 109.5 . . ?
C17 O4 H4 109.5 . . ?
C20 O5 C23 108.8(5) . . ?
C21 O6 H6 109.5 . . ?
C28 O7 H7 109.5 . . ?
C36 O8 H8 109.5 . . ?
O1 C1 C2 107.1(5) . . ?
O1 C1 H1A 110.3 . . ?
C2 C1 H1A 110.3 . . ?
O1 C1 H1B 110.3 . . ?
C2 C1 H1B 110.3 . . ?
H1A C1 H1B 108.6 . . ?
O2 C2 C1 113.0(6) . . ?
O2 C2 C3 112.8(6) . . ?
C1 C2 C3 102.9(5) . . ?
O2 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C4 C3 C2 101.1(5) . . ?
C4 C3 C18 112.4(6) . . ?
C2 C3 C18 113.1(6) . . ?
C4 C3 C8 107.7(6) . . ?
C2 C3 C8 111.1(6) . . ?
C18 C3 C8 110.9(6) . . ?
O1 C4 C5 110.1(5) . . ?
O1 C4 C3 104.7(5) . . ?
C5 C4 C3 117.2(6) . . ?
O1 C4 H4A 108.2 . . ?
C5 C4 H4A 108.2 . . ?
C3 C4 H4A 108.2 . . ?
C6 C5 C9 118.6(6) . . ?
C6 C5 C4 122.8(6) . . ?
C9 C5 C4 118.6(6) . . ?
C5 C6 C12 122.4(6) . . ?
C5 C6 C7 119.8(6) . . ?
C12 C6 C7 117.7(6) . . ?
C6 C7 C8 113.6(5) . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C3 C8 C7 113.7(6) . . ?
C3 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
C3 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
O3 C9 C5 117.7(6) . . ?
O3 C9 C10 122.1(6) . . ?
C5 C9 C10 120.2(6) . . ?
C11 C10 C9 119.9(6) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.8(6) . . ?
C10 C11 C16 117.4(6) . . ?
C12 C11 C16 121.7(6) . . ?
C11 C12 C6 117.8(6) . . ?
C11 C12 C13 122.1(6) . . ?
C6 C12 C13 119.9(6) . . ?
C14 C13 C12 113.4(9) . . ?
C14 C13 C14' 27.3(8) . . ?
C12 C13 C14' 110.8(10) . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C14' C13 H13A 131.0 . . ?
C14 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C14' C13 H13B 85.2 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 H13C 128.4 . . ?
C12 C13 H13C 109.8 . . ?
C14' C13 H13C 110.0 . . ?
H13A C13 H13C 81.5 . . ?
H13B C13 H13C 27.9 . . ?
C14 C13 H13D 83.0 . . ?
C12 C13 H13D 109.5 . . ?
C14' C13 H13D 108.8 . . ?
H13A C13 H13D 29.0 . . ?
H13B C13 H13D 130.4 . . ?
H13C C13 H13D 107.9 . . ?
C13 C14 C15 107.8(19) . . ?
C13 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
C13 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 C16 110.6(17) . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C15' C14' C13 114(2) . . ?
C15' C14' H14C 108.8 . . ?
C13 C14' H14C 108.8 . . ?
C15' C14' H14D 108.8 . . ?
C13 C14' H14D 108.8 . . ?
H14C C14' H14D 107.7 . . ?
C16 C15' C14' 110(2) . . ?
C16 C15' H15C 109.8 . . ?
C14' C15' H15C 109.8 . . ?
C16 C15' H15D 109.8 . . ?
C14' C15' H15D 109.8 . . ?
H15C C15' H15D 108.2 . . ?
C19 C16 C15' 82.4(11) . . ?
C19 C16 C17 117.8(11) . . ?
C15' C16 C17 126.0(14) . . ?
C19 C16 C11 114.4(12) . . ?
C15' C16 C11 110.5(9) . . ?
C17 C16 C11 105.0(6) . . ?
C19 C16 C15 110.3(10) . . ?
C15' C16 C15 32.1(8) . . ?
C17 C16 C15 97.7(10) . . ?
C11 C16 C15 110.3(7) . . ?
C19 C16 C19' 23.5(10) . . ?
C15' C16 C19' 105.5(12) . . ?
C17 C16 C19' 99.6(13) . . ?
C11 C16 C19' 109.0(12) . . ?
C15 C16 C19' 130.8(11) . . ?
O4 C17 C16 111.0(6) . . ?
O4 C17 H17A 109.4 . . ?
C16 C17 H17A 109.4 . . ?
O4 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
C16 C19' H19D 109.5 . . ?
C16 C19' H19E 109.5 . . ?
H19D C19' H19E 109.5 . . ?
C16 C19' H19F 109.5 . . ?
H19D C19' H19F 109.5 . . ?
H19E C19' H19F 109.5 . . ?
O5 C20 C21 106.6(5) . . ?
O5 C20 H20A 110.4 . . ?
C21 C20 H20A 110.4 . . ?
O5 C20 H20B 110.4 . . ?
C21 C20 H20B 110.4 . . ?
H20A C20 H20B 108.6 . . ?
O6 C21 C22 116.5(6) . . ?
O6 C21 C20 111.7(6) . . ?
C22 C21 C20 103.2(5) . . ?
O6 C21 H21 108.4 . . ?
C22 C21 H21 108.4 . . ?
C20 C21 H21 108.4 . . ?
C37 C22 C21 111.9(6) . . ?
C37 C22 C23 113.5(6) . . ?
C21 C22 C23 100.7(5) . . ?
C37 C22 C27 111.4(6) . . ?
C21 C22 C27 109.9(6) . . ?
C23 C22 C27 108.8(5) . . ?
O5 C23 C24 108.9(5) . . ?
O5 C23 C22 105.3(5) . . ?
C24 C23 C22 117.1(5) . . ?
O5 C23 H23 108.4 . . ?
C24 C23 H23 108.4 . . ?
C22 C23 H23 108.4 . . ?
C25 C24 C28 118.6(6) . . ?
C25 C24 C23 123.2(6) . . ?
C28 C24 C23 118.2(6) . . ?
C31 C25 C24 121.0(6) . . ?
C31 C25 C26 120.7(6) . . ?
C24 C25 C26 118.2(6) . . ?
C25 C26 C27 114.9(5) . . ?
C25 C26 H26A 108.6 . . ?
C27 C26 H26A 108.6 . . ?
C25 C26 H26B 108.6 . . ?
C27 C26 H26B 108.6 . . ?
H26A C26 H26B 107.5 . . ?
C26 C27 C22 113.0(5) . . ?
C26 C27 H27A 109.0 . . ?
C22 C27 H27A 109.0 . . ?
C26 C27 H27B 109.0 . . ?
C22 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
O7 C28 C29 122.8(6) . . ?
O7 C28 C24 117.0(6) . . ?
C29 C28 C24 120.2(6) . . ?
C28 C29 C30 121.4(6) . . ?
C28 C29 H29 119.3 . . ?
C30 C29 H29 119.3 . . ?
C31 C30 C29 118.5(6) . . ?
C31 C30 C35 123.6(6) . . ?
C29 C30 C35 117.9(6) . . ?
C25 C31 C30 120.2(6) . . ?
C25 C31 C32 120.3(5) . . ?
C30 C31 C32 119.4(6) . . ?
C33 C32 C31 112.7(5) . . ?
C33 C32 H32A 109.0 . . ?
C31 C32 H32A 109.0 . . ?
C33 C32 H32B 109.0 . . ?
C31 C32 H32B 109.0 . . ?
H32A C32 H32B 107.8 . . ?
C32 C33 C34 109.3(6) . . ?
C32 C33 H33A 109.8 . . ?
C34 C33 H33A 109.8 . . ?
C32 C33 H33B 109.8 . . ?
C34 C33 H33B 109.8 . . ?
H33A C33 H33B 108.3 . . ?
C33 C34 C35 112.2(5) . . ?
C33 C34 H34A 109.2 . . ?
C35 C34 H34A 109.2 . . ?
C33 C34 H34B 109.2 . . ?
C35 C34 H34B 109.2 . . ?
H34A C34 H34B 107.9 . . ?
C36 C35 C30 111.4(6) . . ?
C36 C35 C34 109.2(5) . . ?
C30 C35 C34 112.3(5) . . ?
C36 C35 C38 105.8(6) . . ?
C30 C35 C38 108.1(5) . . ?
C34 C35 C38 109.9(6) . . ?
O8 C36 C35 111.0(5) . . ?
O8 C36 H36A 109.4 . . ?
C35 C36 H36A 109.4 . . ?
O8 C36 H36B 109.4 . . ?
C35 C36 H36B 109.4 . . ?
H36A C36 H36B 108.0 . . ?
C22 C37 H37A 109.5 . . ?
C22 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C22 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 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
C4 O1 C1 C2 -2.7(7) . . . . ?
O1 C1 C2 O2 147.6(6) . . . . ?
O1 C1 C2 C3 25.7(7) . . . . ?
O2 C2 C3 C4 -159.5(6) . . . . ?
C1 C2 C3 C4 -37.4(7) . . . . ?
O2 C2 C3 C18 80.1(8) . . . . ?
C1 C2 C3 C18 -157.8(6) . . . . ?
O2 C2 C3 C8 -45.5(8) . . . . ?
C1 C2 C3 C8 76.6(7) . . . . ?
C1 O1 C4 C5 -148.5(5) . . . . ?
C1 O1 C4 C3 -21.6(7) . . . . ?
C2 C3 C4 O1 36.5(7) . . . . ?
C18 C3 C4 O1 157.4(6) . . . . ?
C8 C3 C4 O1 -80.1(6) . . . . ?
C2 C3 C4 C5 158.7(6) . . . . ?
C18 C3 C4 C5 -80.3(8) . . . . ?
C8 C3 C4 C5 42.2(8) . . . . ?
O1 C4 C5 C6 104.6(7) . . . . ?
C3 C4 C5 C6 -14.9(9) . . . . ?
O1 C4 C5 C9 -76.3(7) . . . . ?
C3 C4 C5 C9 164.2(6) . . . . ?
C9 C5 C6 C12 -2.6(9) . . . . ?
C4 C5 C6 C12 176.5(6) . . . . ?
C9 C5 C6 C7 -179.1(6) . . . . ?
C4 C5 C6 C7 0.0(9) . . . . ?
C5 C6 C7 C8 -15.0(9) . . . . ?
C12 C6 C7 C8 168.3(6) . . . . ?
C4 C3 C8 C7 -57.6(7) . . . . ?
C2 C3 C8 C7 -167.5(5) . . . . ?
C18 C3 C8 C7 65.8(7) . . . . ?
C6 C7 C8 C3 45.2(8) . . . . ?
C6 C5 C9 O3 -177.0(6) . . . . ?
C4 C5 C9 O3 3.9(9) . . . . ?
C6 C5 C9 C10 3.9(9) . . . . ?
C4 C5 C9 C10 -175.2(6) . . . . ?
O3 C9 C10 C11 180.0(6) . . . . ?
C5 C9 C10 C11 -1.0(10) . . . . ?
C9 C10 C11 C12 -3.3(10) . . . . ?
C9 C10 C11 C16 173.1(6) . . . . ?
C10 C11 C12 C6 4.5(9) . . . . ?
C16 C11 C12 C6 -171.7(6) . . . . ?
C10 C11 C12 C13 -172.1(6) . . . . ?
C16 C11 C12 C13 11.6(10) . . . . ?
C5 C6 C12 C11 -1.5(9) . . . . ?
C7 C6 C12 C11 175.0(6) . . . . ?
C5 C6 C12 C13 175.2(6) . . . . ?
C7 C6 C12 C13 -8.3(9) . . . . ?
C11 C12 C13 C14 15.1(15) . . . . ?
C6 C12 C13 C14 -161.5(13) . . . . ?
C11 C12 C13 C14' -14.2(17) . . . . ?
C6 C12 C13 C14' 169.2(15) . . . . ?
C12 C13 C14 C15 -53(2) . . . . ?
C14' C13 C14 C15 37(3) . . . . ?
C13 C14 C15 C16 67(3) . . . . ?
C14 C13 C14' C15' -61(4) . . . . ?
C12 C13 C14' C15' 40(3) . . . . ?
C13 C14' C15' C16 -62(4) . . . . ?
C14' C15' C16 C19 169(3) . . . . ?
C14' C15' C16 C17 -72(2) . . . . ?
C14' C15' C16 C11 56(3) . . . . ?
C14' C15' C16 C15 -40(3) . . . . ?
C14' C15' C16 C19' 173(3) . . . . ?
C10 C11 C16 C19 60.7(13) . . . . ?
C12 C11 C16 C19 -122.9(12) . . . . ?
C10 C11 C16 C15' 151.5(16) . . . . ?
C12 C11 C16 C15' -32.1(17) . . . . ?
C10 C11 C16 C17 -69.9(7) . . . . ?
C12 C11 C16 C17 106.5(7) . . . . ?
C10 C11 C16 C15 -174.2(12) . . . . ?
C12 C11 C16 C15 2.2(13) . . . . ?
C10 C11 C16 C19' 36.1(15) . . . . ?
C12 C11 C16 C19' -147.6(14) . . . . ?
C14 C15 C16 C19 87(2) . . . . ?
C14 C15 C16 C15' 56(2) . . . . ?
C14 C15 C16 C17 -149.8(18) . . . . ?
C14 C15 C16 C11 -41(2) . . . . ?
C14 C15 C16 C19' 100(3) . . . . ?
C19 C16 C17 O4 53.6(14) . . . . ?
C15' C16 C17 O4 -47.8(14) . . . . ?
C11 C16 C17 O4 -177.8(5) . . . . ?
C15 C16 C17 O4 -64.3(9) . . . . ?
C19' C16 C17 O4 69.4(12) . . . . ?
C23 O5 C20 C21 -4.3(7) . . . . ?
O5 C20 C21 O6 152.9(5) . . . . ?
O5 C20 C21 C22 26.9(7) . . . . ?
O6 C21 C22 C37 78.8(8) . . . . ?
C20 C21 C22 C37 -158.5(6) . . . . ?
O6 C21 C22 C23 -160.4(6) . . . . ?
C20 C21 C22 C23 -37.6(7) . . . . ?
O6 C21 C22 C27 -45.7(8) . . . . ?
C20 C21 C22 C27 77.1(6) . . . . ?
C20 O5 C23 C24 -146.6(5) . . . . ?
C20 O5 C23 C22 -20.2(7) . . . . ?
C37 C22 C23 O5 155.6(5) . . . . ?
C21 C22 C23 O5 35.8(7) . . . . ?
C27 C22 C23 O5 -79.7(6) . . . . ?
C37 C22 C23 C24 -83.3(8) . . . . ?
C21 C22 C23 C24 156.9(6) . . . . ?
C27 C22 C23 C24 41.4(8) . . . . ?
O5 C23 C24 C25 101.5(7) . . . . ?
C22 C23 C24 C25 -17.7(9) . . . . ?
O5 C23 C24 C28 -75.9(7) . . . . ?
C22 C23 C24 C28 164.8(6) . . . . ?
C28 C24 C25 C31 0.6(10) . . . . ?
C23 C24 C25 C31 -176.8(6) . . . . ?
C28 C24 C25 C26 -176.6(6) . . . . ?
C23 C24 C25 C26 5.9(9) . . . . ?
C31 C25 C26 C27 162.3(6) . . . . ?
C24 C25 C26 C27 -20.5(9) . . . . ?
C25 C26 C27 C22 46.6(8) . . . . ?
C37 C22 C27 C26 69.8(7) . . . . ?
C21 C22 C27 C26 -165.5(5) . . . . ?
C23 C22 C27 C26 -56.1(7) . . . . ?
C25 C24 C28 O7 -178.6(6) . . . . ?
C23 C24 C28 O7 -1.0(9) . . . . ?
C25 C24 C28 C29 2.5(10) . . . . ?
C23 C24 C28 C29 -179.9(6) . . . . ?
O7 C28 C29 C30 177.7(6) . . . . ?
C24 C28 C29 C30 -3.5(10) . . . . ?
C28 C29 C30 C31 1.3(9) . . . . ?
C28 C29 C30 C35 -176.9(6) . . . . ?
C24 C25 C31 C30 -2.8(10) . . . . ?
C26 C25 C31 C30 174.4(6) . . . . ?
C24 C25 C31 C32 173.9(6) . . . . ?
C26 C25 C31 C32 -9.0(9) . . . . ?
C29 C30 C31 C25 1.8(9) . . . . ?
C35 C30 C31 C25 179.9(6) . . . . ?
C29 C30 C31 C32 -174.9(6) . . . . ?
C35 C30 C31 C32 3.3(9) . . . . ?
C25 C31 C32 C33 -154.7(6) . . . . ?
C30 C31 C32 C33 21.9(8) . . . . ?
C31 C32 C33 C34 -54.2(7) . . . . ?
C32 C33 C34 C35 63.3(8) . . . . ?
C31 C30 C35 C36 127.6(6) . . . . ?
C29 C30 C35 C36 -54.3(8) . . . . ?
C31 C30 C35 C34 4.7(9) . . . . ?
C29 C30 C35 C34 -177.1(6) . . . . ?
C31 C30 C35 C38 -116.7(7) . . . . ?
C29 C30 C35 C38 61.5(8) . . . . ?
C33 C34 C35 C36 -161.9(6) . . . . ?
C33 C34 C35 C30 -37.8(8) . . . . ?
C33 C34 C35 C38 82.6(7) . . . . ?
C30 C35 C36 O8 -71.2(7) . . . . ?
C34 C35 C36 O8 53.4(7) . . . . ?
C38 C35 C36 O8 171.6(6) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        65.94
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.054
