# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2003


data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Brian P. Roberts'
'Hai-Shan Dang'
'D. Tocher'

_publ_contact_author_name        'Dr Brian P Roberts'
_publ_contact_author_address     
;
Department of Chemistry
University College London
Christopher Ingold Laboratories
20 Gordon Street
London
WC1H OAJ
UNITED KINGDOM
;

_publ_contact_author_email       B.P.ROBERTS@UCL.AC.UK

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
Thiol-catalysed radical-chain redox rearrangement
reactions of benzylidene acetals derived from terpenoid dios
;

data_str0166_Compound_58
_database_code_CSD               216435

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H28 O2'
_chemical_formula_weight         288.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   8.5195(11)
_cell_length_b                   10.0386(13)
_cell_length_c                   19.370(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1656.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9646
_exptl_absorpt_correction_T_max  0.9942
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 SMART APEX diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14785
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         28.26
_reflns_number_total             3974
_reflns_number_gt                3275
_reflns_threshold_expression     I>2σ(I)

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

_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)+(0.0606P)²+0.0651P] 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       0.019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.0(13)
_refine_ls_number_reflns         3974
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1251
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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 0.09853(12) 0.15854(11) 1.01911(5) 0.0363(3) Uani 1 1 d . . .
O2 O 0.12026(14) 0.36812(11) 0.97244(5) 0.0423(3) Uani 1 1 d . . .
C1 C 0.1739(2) 0.28297(16) 1.02415(8) 0.0364(4) Uani 1 1 d . . .
H1 H 0.2874 0.2704 1.0189 0.044 Uiso 1 1 calc R . .
C2 C 0.14091(19) 0.34320(17) 1.09380(8) 0.0375(4) Uani 1 1 d . . .
C3 C 0.1198(2) 0.47872(18) 1.10138(9) 0.0470(5) Uani 1 1 d . . .
H3 H 0.1198 0.5334 1.0626 0.056 Uiso 1 1 calc R . .
C4 C 0.0985(2) 0.5341(2) 1.16628(10) 0.0581(5) Uani 1 1 d . . .
H4 H 0.0841 0.6256 1.1706 0.070 Uiso 1 1 calc R . .
C5 C 0.0986(3) 0.4559(2) 1.22370(10) 0.0591(6) Uani 1 1 d . . .
H5 H 0.0845 0.4936 1.2671 0.071 Uiso 1 1 calc R . .
C6 C 0.1196(3) 0.3209(2) 1.21706(10) 0.0582(5) Uani 1 1 d . . .
H6 H 0.1195 0.2670 1.2561 0.070 Uiso 1 1 calc R . .
C7 C 0.1408(2) 0.2644(2) 1.15244(9) 0.0487(4) Uani 1 1 d . . .
H7 H 0.1551 0.1728 1.1485 0.058 Uiso 1 1 calc R . .
C8 C 0.0925(3) 0.4280(2) 0.85756(9) 0.0586(6) Uani 1 1 d . . .
H8A H -0.0193 0.4164 0.8557 0.088 Uiso 1 1 calc R . .
H8B H 0.1355 0.4189 0.8120 0.088 Uiso 1 1 calc R . .
H8C H 0.1163 0.5150 0.8753 0.088 Uiso 1 1 calc R . .
C9 C 0.1634(2) 0.32299(18) 0.90452(8) 0.0409(4) Uani 1 1 d . . .
H9 H 0.2780 0.3251 0.9000 0.049 Uiso 1 1 calc R . .
C10 C 0.1053(2) 0.17975(17) 0.89320(8) 0.0380(4) Uani 1 1 d . . .
H10 H -0.0093 0.1822 0.8889 0.046 Uiso 1 1 calc R . .
C11 C 0.14647(19) 0.09394(16) 0.95619(8) 0.0347(4) Uani 1 1 d . . .
H11 H 0.2607 0.0829 0.9575 0.042 Uiso 1 1 calc R . .
C12 C 0.0720(2) -0.04398(17) 0.95364(9) 0.0408(4) Uani 1 1 d . . .
H12 H -0.0413 -0.0317 0.9478 0.049 Uiso 1 1 calc R . .
C13 C 0.0970(2) -0.13141(17) 1.01822(9) 0.0484(5) Uani 1 1 d . . .
H13 H 0.0811 -0.2237 1.0034 0.058 Uiso 1 1 calc R . .
C14 C 0.2634(3) -0.1242(2) 1.04711(11) 0.0672(6) Uani 1 1 d . . .
H14A H 0.2804 -0.0382 1.0674 0.101 Uiso 1 1 calc R . .
H14B H 0.3375 -0.1380 1.0105 0.101 Uiso 1 1 calc R . .
H14C H 0.2770 -0.1919 1.0816 0.101 Uiso 1 1 calc R . .
C15 C -0.0238(3) -0.1050(2) 1.07436(10) 0.0656(6) Uani 1 1 d . . .
H15A H -0.0079 -0.0174 1.0930 0.098 Uiso 1 1 calc R . .
H15B H -0.0124 -0.1699 1.1104 0.098 Uiso 1 1 calc R . .
H15C H -0.1274 -0.1110 1.0551 0.098 Uiso 1 1 calc R . .
C16 C 0.1335(3) -0.11318(19) 0.88864(9) 0.0551(5) Uani 1 1 d . . .
H16A H 0.2453 -0.1290 0.8936 0.066 Uiso 1 1 calc R . .
H16B H 0.0821 -0.1989 0.8837 0.066 Uiso 1 1 calc R . .
C17 C 0.1050(3) -0.0312(2) 0.82429(9) 0.0589(6) Uani 1 1 d . . .
H17A H -0.0072 -0.0255 0.8162 0.071 Uiso 1 1 calc R . .
H17B H 0.1515 -0.0766 0.7851 0.071 Uiso 1 1 calc R . .
C18 C 0.1724(2) 0.1098(2) 0.82857(8) 0.0485(5) Uani 1 1 d . . .
H18 H 0.2861 0.1017 0.8349 0.058 Uiso 1 1 calc R . .
C19 C 0.1446(3) 0.1794(3) 0.75959(10) 0.0806(8) Uani 1 1 d . . .
H19A H 0.1726 0.1204 0.7226 0.121 Uiso 1 1 calc R . .
H19B H 0.2080 0.2583 0.7572 0.121 Uiso 1 1 calc R . .
H19C H 0.0359 0.2032 0.7556 0.121 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 1.4079(19) . ?
O1 C11 1.4397(18) . ?
O2 C1 1.3939(19) . ?
O2 C9 1.4392(19) . ?
C1 C2 1.505(2) . ?
C2 C3 1.380(3) . ?
C2 C7 1.384(2) . ?
C3 C4 1.386(3) . ?
C4 C5 1.362(3) . ?
C5 C6 1.373(3) . ?
C6 C7 1.386(3) . ?
C8 C9 1.518(2) . ?
C9 C10 1.537(2) . ?
C10 C11 1.534(2) . ?
C10 C18 1.545(2) . ?
C11 C12 1.524(2) . ?
C12 C16 1.530(2) . ?
C12 C13 1.543(2) . ?
C13 C15 1.521(3) . ?
C13 C14 1.526(3) . ?
C16 C17 1.513(3) . ?
C17 C18 1.530(3) . ?
C18 C19 1.526(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 C11 109.20(11) . . ?
C1 O2 C9 112.33(12) . . ?
O2 C1 O1 110.16(13) . . ?
O2 C1 C2 109.66(13) . . ?
O1 C1 C2 109.48(13) . . ?
C3 C2 C7 118.44(16) . . ?
C3 C2 C1 121.05(16) . . ?
C7 C2 C1 120.40(16) . . ?
C2 C3 C4 120.59(18) . . ?
C5 C4 C3 120.61(18) . . ?
C4 C5 C6 119.53(18) . . ?
C5 C6 C7 120.37(19) . . ?
C2 C7 C6 120.47(18) . . ?
O2 C9 C8 103.16(14) . . ?
O2 C9 C10 110.04(13) . . ?
C8 C9 C10 115.85(15) . . ?
C11 C10 C9 109.77(13) . . ?
C11 C10 C18 107.73(14) . . ?
C9 C10 C18 114.95(15) . . ?
O1 C11 C12 108.58(12) . . ?
O1 C11 C10 110.82(12) . . ?
C12 C11 C10 112.90(13) . . ?
C11 C12 C16 107.26(14) . . ?
C11 C12 C13 115.67(14) . . ?
C16 C12 C13 111.20(14) . . ?
C15 C13 C14 111.00(17) . . ?
C15 C13 C12 112.78(15) . . ?
C14 C13 C12 113.49(16) . . ?
C17 C16 C12 112.08(16) . . ?
C16 C17 C18 113.46(16) . . ?
C19 C18 C17 108.55(16) . . ?
C19 C18 C10 116.36(17) . . ?
C17 C18 C10 109.01(15) . . ?

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
C9 O2 C1 O1 -65.71(17) . . . . ?
C9 O2 C1 C2 173.73(13) . . . . ?
C11 O1 C1 O2 66.58(15) . . . . ?
C11 O1 C1 C2 -172.75(13) . . . . ?
O2 C1 C2 C3 -22.7(2) . . . . ?
O1 C1 C2 C3 -143.64(17) . . . . ?
O2 C1 C2 C7 161.37(16) . . . . ?
O1 C1 C2 C7 40.4(2) . . . . ?
C7 C2 C3 C4 -0.2(3) . . . . ?
C1 C2 C3 C4 -176.22(16) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
C3 C2 C7 C6 0.1(3) . . . . ?
C1 C2 C7 C6 176.21(18) . . . . ?
C5 C6 C7 C2 -0.1(3) . . . . ?
C1 O2 C9 C8 179.38(14) . . . . ?
C1 O2 C9 C10 55.20(18) . . . . ?
O2 C9 C10 C11 -46.58(19) . . . . ?
C8 C9 C10 C11 -163.06(15) . . . . ?
O2 C9 C10 C18 -168.18(14) . . . . ?
C8 C9 C10 C18 75.3(2) . . . . ?
C1 O1 C11 C12 176.52(13) . . . . ?
C1 O1 C11 C10 -58.93(16) . . . . ?
C9 C10 C11 O1 49.52(18) . . . . ?
C18 C10 C11 O1 175.35(13) . . . . ?
C9 C10 C11 C12 171.57(13) . . . . ?
C18 C10 C11 C12 -62.59(18) . . . . ?
O1 C11 C12 C16 -176.44(13) . . . . ?
C10 C11 C12 C16 60.25(18) . . . . ?
O1 C11 C12 C13 -51.73(18) . . . . ?
C10 C11 C12 C13 -175.04(14) . . . . ?
C11 C12 C13 C15 85.32(19) . . . . ?
C16 C12 C13 C15 -152.03(18) . . . . ?
C11 C12 C13 C14 -42.0(2) . . . . ?
C16 C12 C13 C14 80.6(2) . . . . ?
C11 C12 C16 C17 -54.7(2) . . . . ?
C13 C12 C16 C17 177.97(16) . . . . ?
C12 C16 C17 C18 55.1(2) . . . . ?
C16 C17 C18 C19 176.79(18) . . . . ?
C16 C17 C18 C10 -55.6(2) . . . . ?
C11 C10 C18 C19 -179.84(17) . . . . ?
C9 C10 C18 C19 -57.1(2) . . . . ?
C11 C10 C18 C17 57.05(19) . . . . ?
C9 C10 C18 C17 179.76(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.033

data_str0154_Compound_30
_database_code_CSD               216436

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H42 O4'
_chemical_formula_weight         514.68

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                   10.6743(7)
_cell_length_b                   16.4346(10)
_cell_length_c                   16.6813(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2926.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9650
_exptl_absorpt_correction_T_max  0.9940
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 SMART APEX diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26059
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         28.33
_reflns_number_total             6887
_reflns_number_gt                5908
_reflns_threshold_expression     I>2σ(I)

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

_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)+(0.0634P)²+0.1579P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(8)
_refine_ls_number_reflns         6887
_refine_ls_number_parameters     349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1136
_refine_ls_wR_factor_gt          0.1077
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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 0.32379(9) 0.56017(7) 0.00712(6) 0.0535(2) Uani 1 1 d . . .
O2 O 0.11248(9) 0.57868(6) 0.01045(6) 0.0490(2) Uani 1 1 d . . .
O3 O 0.19957(10) 0.41654(6) 0.01927(6) 0.0536(2) Uani 1 1 d . . .
O4 O 0.30473(9) 0.44746(6) 0.13393(6) 0.0515(2) Uani 1 1 d . . .
C1 C 0.2454(3) 0.88622(12) -0.00699(15) 0.0971(7) Uani 1 1 d . . .
H1A H 0.1756 0.9215 -0.0175 0.146 Uiso 1 1 calc R . .
H1B H 0.3222 0.9156 -0.0149 0.146 Uiso 1 1 calc R . .
H1C H 0.2412 0.8671 0.0473 0.146 Uiso 1 1 calc R . .
C2 C 0.2471(2) 0.83880(13) -0.15014(12) 0.0805(6) Uani 1 1 d . . .
H2A H 0.2541 0.7910 -0.1830 0.121 Uiso 1 1 calc R . .
H2B H 0.3188 0.8730 -0.1586 0.121 Uiso 1 1 calc R . .
H2C H 0.1724 0.8680 -0.1643 0.121 Uiso 1 1 calc R . .
C3 C 0.24096(19) 0.81439(10) -0.06370(11) 0.0669(4) Uani 1 1 d . . .
C4 C 0.30344(17) 0.73774(10) -0.03230(10) 0.0610(4) Uani 1 1 d . . .
H4 H 0.3409 0.7422 0.0211 0.073 Uiso 1 1 calc R . .
C5 C 0.16191(16) 0.74401(10) -0.03513(10) 0.0582(4) Uani 1 1 d . . .
H5 H 0.1206 0.7518 0.0168 0.070 Uiso 1 1 calc R . .
C6 C 0.10151(16) 0.68261(11) -0.08961(10) 0.0599(4) Uani 1 1 d . . .
H6A H 0.1207 0.6959 -0.1449 0.072 Uiso 1 1 calc R . .
H6B H 0.0113 0.6847 -0.0830 0.072 Uiso 1 1 calc R . .
C7 C 0.14780(15) 0.59718(10) -0.07111(9) 0.0522(3) Uani 1 1 d . . .
C8 C 0.29204(14) 0.59141(9) -0.06993(8) 0.0515(3) Uani 1 1 d . . .
H8 H 0.3190 0.5524 -0.1109 0.062 Uiso 1 1 calc R . .
C9 C 0.35681(16) 0.67218(11) -0.08487(12) 0.0642(4) Uani 1 1 d . . .
H9A H 0.4457 0.6666 -0.0742 0.077 Uiso 1 1 calc R . .
H9B H 0.3467 0.6874 -0.1407 0.077 Uiso 1 1 calc R . .
C10 C 0.0888(2) 0.53462(12) -0.12661(10) 0.0742(5) Uani 1 1 d . . .
H10A H 0.1156 0.4811 -0.1112 0.111 Uiso 1 1 calc R . .
H10B H 0.1143 0.5452 -0.1808 0.111 Uiso 1 1 calc R . .
H10C H -0.0008 0.5380 -0.1228 0.111 Uiso 1 1 calc R . .
C11 C 0.21733(13) 0.55813(8) 0.05732(8) 0.0455(3) Uani 1 1 d . . .
C12 C 0.23424(16) 0.61671(9) 0.12679(9) 0.0518(3) Uani 1 1 d . . .
C13 C 0.13393(19) 0.66122(10) 0.15566(10) 0.0651(4) Uani 1 1 d . . .
H13 H 0.0545 0.6540 0.1339 0.078 Uiso 1 1 calc R . .
C14 C 0.1524(3) 0.71669(12) 0.21737(13) 0.0858(7) Uani 1 1 d . . .
H14 H 0.0854 0.7475 0.2361 0.103 Uiso 1 1 calc R . .
C15 C 0.2689(3) 0.72632(13) 0.25088(13) 0.0961(8) Uani 1 1 d . . .
H15 H 0.2805 0.7630 0.2926 0.115 Uiso 1 1 calc R . .
C16 C 0.3677(3) 0.68205(14) 0.22296(13) 0.0906(7) Uani 1 1 d . . .
H16 H 0.4465 0.6888 0.2458 0.109 Uiso 1 1 calc R . .
C17 C 0.3517(2) 0.62685(11) 0.16050(11) 0.0703(5) Uani 1 1 d . . .
H17 H 0.4195 0.5970 0.1415 0.084 Uiso 1 1 calc R . .
C18 C 0.3238(2) 0.12460(12) 0.10234(14) 0.0885(6) Uani 1 1 d . . .
H18A H 0.3932 0.1547 0.0809 0.133 Uiso 1 1 calc R . .
H18B H 0.3029 0.0809 0.0666 0.133 Uiso 1 1 calc R . .
H18C H 0.3463 0.1027 0.1537 0.133 Uiso 1 1 calc R . .
C19 C 0.0970(3) 0.13620(13) 0.13997(14) 0.0896(7) Uani 1 1 d . . .
H19A H 0.1121 0.1136 0.1922 0.134 Uiso 1 1 calc R . .
H19B H 0.0770 0.0932 0.1031 0.134 Uiso 1 1 calc R . .
H19C H 0.0282 0.1738 0.1427 0.134 Uiso 1 1 calc R . .
C20 C 0.21266(19) 0.18014(10) 0.11155(10) 0.0627(4) Uani 1 1 d . . .
C21 C 0.18930(16) 0.25134(9) 0.05636(9) 0.0557(4) Uani 1 1 d . . .
H21 H 0.1009 0.2622 0.0447 0.067 Uiso 1 1 calc R . .
C22 C 0.22778(17) 0.26607(9) 0.14232(9) 0.0559(4) Uani 1 1 d . . .
H22 H 0.1618 0.2857 0.1783 0.067 Uiso 1 1 calc R . .
C23 C 0.35418(18) 0.30535(10) 0.15199(11) 0.0664(5) Uani 1 1 d . . .
H23A H 0.4185 0.2658 0.1389 0.080 Uiso 1 1 calc R . .
H23B H 0.3652 0.3208 0.2077 0.080 Uiso 1 1 calc R . .
C24 C 0.37232(14) 0.38067(10) 0.09927(10) 0.0545(4) Uani 1 1 d . . .
C25 C 0.31360(15) 0.37086(10) 0.01590(9) 0.0555(4) Uani 1 1 d . . .
H25 H 0.3694 0.3934 -0.0251 0.067 Uiso 1 1 calc R . .
C26 C 0.27960(18) 0.28331(10) -0.00465(10) 0.0622(4) Uani 1 1 d . . .
H26A H 0.2420 0.2811 -0.0575 0.075 Uiso 1 1 calc R . .
H26B H 0.3546 0.2500 -0.0051 0.075 Uiso 1 1 calc R . .
C27 C 0.50903(16) 0.40506(14) 0.09538(16) 0.0852(6) Uani 1 1 d . . .
H27A H 0.5167 0.4558 0.0673 0.128 Uiso 1 1 calc R . .
H27B H 0.5557 0.3638 0.0676 0.128 Uiso 1 1 calc R . .
H27C H 0.5413 0.4110 0.1488 0.128 Uiso 1 1 calc R . .
C28 C 0.20019(12) 0.46803(8) 0.08672(8) 0.0446(3) Uani 1 1 d . . .
C29 C 0.07941(13) 0.45634(8) 0.13346(8) 0.0462(3) Uani 1 1 d . . .
C30 C -0.03027(15) 0.43920(11) 0.09320(11) 0.0632(4) Uani 1 1 d . . .
H30 H -0.0303 0.4357 0.0376 0.076 Uiso 1 1 calc R . .
C31 C -0.14009(18) 0.42723(13) 0.13528(14) 0.0789(5) Uani 1 1 d . . .
H31 H -0.2140 0.4159 0.1079 0.095 Uiso 1 1 calc R . .
C32 C -0.14038(18) 0.43205(12) 0.21748(14) 0.0758(5) Uani 1 1 d . . .
H32 H -0.2142 0.4235 0.2458 0.091 Uiso 1 1 calc R . .
C33 C -0.03226(18) 0.44940(11) 0.25748(11) 0.0694(5) Uani 1 1 d . . .
H33 H -0.0327 0.4531 0.3131 0.083 Uiso 1 1 calc R . .
C34 C 0.07838(16) 0.46162(10) 0.21569(9) 0.0578(4) Uani 1 1 d . . .
H34 H 0.1519 0.4734 0.2433 0.069 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 C11 1.4120(17) . ?
O1 C8 1.4248(18) . ?
O2 C11 1.4064(17) . ?
O2 C7 1.4442(18) . ?
O3 C28 1.4079(16) . ?
O3 C25 1.4312(19) . ?
O4 C28 1.4071(16) . ?
O4 C24 1.4352(18) . ?
C1 C3 1.513(3) . ?
C2 C3 1.498(3) . ?
C3 C5 1.509(2) . ?
C3 C4 1.519(2) . ?
C4 C9 1.501(2) . ?
C4 C5 1.515(2) . ?
C5 C6 1.503(2) . ?
C6 C7 1.520(2) . ?
C7 C10 1.520(2) . ?
C7 C8 1.543(2) . ?
C8 C9 1.517(2) . ?
C11 C12 1.517(2) . ?
C11 C28 1.5704(19) . ?
C12 C17 1.384(3) . ?
C12 C13 1.383(2) . ?
C13 C14 1.389(3) . ?
C14 C15 1.373(4) . ?
C15 C16 1.363(4) . ?
C16 C17 1.392(3) . ?
C18 C20 1.505(3) . ?
C19 C20 1.507(3) . ?
C20 C21 1.510(2) . ?
C20 C22 1.511(2) . ?
C21 C26 1.497(2) . ?
C21 C22 1.511(2) . ?
C22 C23 1.504(3) . ?
C23 C24 1.531(2) . ?
C24 C27 1.515(2) . ?
C24 C25 1.534(2) . ?
C25 C26 1.523(2) . ?
C28 C29 1.5189(19) . ?
C29 C34 1.374(2) . ?
C29 C30 1.379(2) . ?
C30 C31 1.380(3) . ?
C31 C32 1.373(3) . ?
C32 C33 1.363(3) . ?
C33 C34 1.386(2) . ?

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
C11 O1 C8 110.61(10) . . ?
C11 O2 C7 111.50(10) . . ?
C28 O3 C25 110.04(10) . . ?
C28 O4 C24 110.91(11) . . ?
C2 C3 C5 122.25(17) . . ?
C2 C3 C1 113.04(17) . . ?
C5 C3 C1 114.72(17) . . ?
C2 C3 C4 122.33(18) . . ?
C5 C3 C4 60.05(11) . . ?
C1 C3 C4 114.69(17) . . ?
C9 C4 C5 114.14(14) . . ?
C9 C4 C3 124.09(15) . . ?
C5 C4 C3 59.66(11) . . ?
C6 C5 C3 124.30(15) . . ?
C6 C5 C4 113.64(14) . . ?
C3 C5 C4 60.29(12) . . ?
C5 C6 C7 110.97(13) . . ?
O2 C7 C6 107.51(13) . . ?
O2 C7 C10 108.85(12) . . ?
C6 C7 C10 111.49(14) . . ?
O2 C7 C8 103.62(12) . . ?
C6 C7 C8 112.57(13) . . ?
C10 C7 C8 112.33(15) . . ?
O1 C8 C9 110.80(13) . . ?
O1 C8 C7 105.73(11) . . ?
C9 C8 C7 113.51(14) . . ?
C4 C9 C8 111.04(13) . . ?
O2 C11 O1 107.76(11) . . ?
O2 C11 C12 111.52(12) . . ?
O1 C11 C12 110.01(11) . . ?
O2 C11 C28 107.90(11) . . ?
O1 C11 C28 107.54(11) . . ?
C12 C11 C28 111.93(11) . . ?
C17 C12 C13 119.73(15) . . ?
C17 C12 C11 119.64(15) . . ?
C13 C12 C11 120.62(15) . . ?
C12 C13 C14 119.7(2) . . ?
C15 C14 C13 120.4(2) . . ?
C16 C15 C14 120.01(19) . . ?
C15 C16 C17 120.6(2) . . ?
C12 C17 C16 119.6(2) . . ?
C18 C20 C19 112.80(17) . . ?
C18 C20 C21 122.55(17) . . ?
C19 C20 C21 115.34(18) . . ?
C18 C20 C22 121.15(18) . . ?
C19 C20 C22 115.37(16) . . ?
C21 C20 C22 60.03(10) . . ?
C26 C21 C20 125.47(16) . . ?
C26 C21 C22 114.45(14) . . ?
C20 C21 C22 60.04(10) . . ?
C23 C22 C20 122.22(15) . . ?
C23 C22 C21 114.48(14) . . ?
C20 C22 C21 59.93(10) . . ?
C22 C23 C24 113.50(13) . . ?
O4 C24 C27 107.40(14) . . ?
O4 C24 C23 108.87(13) . . ?
C27 C24 C23 111.13(16) . . ?
O4 C24 C25 103.90(12) . . ?
C27 C24 C25 112.50(16) . . ?
C23 C24 C25 112.59(13) . . ?
O3 C25 C26 107.56(13) . . ?
O3 C25 C24 104.88(11) . . ?
C26 C25 C24 113.63(14) . . ?
C21 C26 C25 109.39(13) . . ?
O4 C28 O3 107.85(10) . . ?
O4 C28 C29 110.82(10) . . ?
O3 C28 C29 109.28(11) . . ?
O4 C28 C11 108.00(11) . . ?
O3 C28 C11 108.52(11) . . ?
C29 C28 C11 112.24(11) . . ?
C34 C29 C30 119.49(15) . . ?
C34 C29 C28 120.74(13) . . ?
C30 C29 C28 119.77(13) . . ?
C29 C30 C31 120.16(17) . . ?
C32 C31 C30 120.09(18) . . ?
C33 C32 C31 119.92(17) . . ?
C32 C33 C34 120.36(17) . . ?
C29 C34 C33 119.98(16) . . ?

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
C2 C3 C4 C9 -11.2(3) . . . . ?
C5 C3 C4 C9 100.14(18) . . . . ?
C1 C3 C4 C9 -154.42(18) . . . . ?
C2 C3 C4 C5 -111.4(2) . . . . ?
C1 C3 C4 C5 105.44(19) . . . . ?
C2 C3 C5 C6 11.7(3) . . . . ?
C1 C3 C5 C6 154.85(18) . . . . ?
C4 C3 C5 C6 -99.76(18) . . . . ?
C2 C3 C5 C4 111.5(2) . . . . ?
C1 C3 C5 C4 -105.39(19) . . . . ?
C9 C4 C5 C6 0.6(2) . . . . ?
C3 C4 C5 C6 117.29(16) . . . . ?
C9 C4 C5 C3 -116.71(17) . . . . ?
C3 C5 C6 C7 120.26(18) . . . . ?
C4 C5 C6 C7 51.13(18) . . . . ?
C11 O2 C7 C6 -122.98(13) . . . . ?
C11 O2 C7 C10 116.11(15) . . . . ?
C11 O2 C7 C8 -3.61(15) . . . . ?
C5 C6 C7 O2 61.58(16) . . . . ?
C5 C6 C7 C10 -179.19(14) . . . . ?
C5 C6 C7 C8 -51.91(18) . . . . ?
C11 O1 C8 C9 114.29(14) . . . . ?
C11 O1 C8 C7 -9.10(15) . . . . ?
O2 C7 C8 O1 7.55(15) . . . . ?
C6 C7 C8 O1 123.40(13) . . . . ?
C10 C7 C8 O1 -109.77(14) . . . . ?
O2 C7 C8 C9 -114.11(14) . . . . ?
C6 C7 C8 C9 1.74(19) . . . . ?
C10 C7 C8 C9 128.58(15) . . . . ?
C5 C4 C9 C8 -51.0(2) . . . . ?
C3 C4 C9 C8 -119.54(18) . . . . ?
O1 C8 C9 C4 -69.51(17) . . . . ?
C7 C8 C9 C4 49.27(19) . . . . ?
C7 O2 C11 O1 -1.77(15) . . . . ?
C7 O2 C11 C12 119.06(13) . . . . ?
C7 O2 C11 C28 -117.62(12) . . . . ?
C8 O1 C11 O2 7.04(15) . . . . ?
C8 O1 C11 C12 -114.74(13) . . . . ?
C8 O1 C11 C28 123.12(11) . . . . ?
O2 C11 C12 C17 -155.60(14) . . . . ?
O1 C11 C12 C17 -36.09(18) . . . . ?
C28 C11 C12 C17 83.41(17) . . . . ?
O2 C11 C12 C13 23.12(19) . . . . ?
O1 C11 C12 C13 142.63(14) . . . . ?
C28 C11 C12 C13 -97.88(16) . . . . ?
C17 C12 C13 C14 1.1(3) . . . . ?
C11 C12 C13 C14 -177.66(15) . . . . ?
C12 C13 C14 C15 -1.3(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C13 C12 C17 C16 -0.3(3) . . . . ?
C11 C12 C17 C16 178.47(17) . . . . ?
C15 C16 C17 C12 -0.3(3) . . . . ?
C18 C20 C21 C26 -9.8(3) . . . . ?
C19 C20 C21 C26 -153.96(16) . . . . ?
C22 C20 C21 C26 100.13(17) . . . . ?
C18 C20 C21 C22 -109.9(2) . . . . ?
C19 C20 C21 C22 105.92(17) . . . . ?
C18 C20 C22 C23 10.6(3) . . . . ?
C19 C20 C22 C23 152.55(18) . . . . ?
C21 C20 C22 C23 -101.60(17) . . . . ?
C18 C20 C22 C21 112.2(2) . . . . ?
C19 C20 C22 C21 -105.86(19) . . . . ?
C26 C21 C22 C23 -3.86(19) . . . . ?
C20 C21 C22 C23 114.42(17) . . . . ?
C26 C21 C22 C20 -118.27(17) . . . . ?
C20 C22 C23 C24 117.77(17) . . . . ?
C21 C22 C23 C24 49.10(19) . . . . ?
C28 O4 C24 C27 129.73(16) . . . . ?
C28 O4 C24 C23 -109.85(14) . . . . ?
C28 O4 C24 C25 10.34(15) . . . . ?
C22 C23 C24 O4 76.10(17) . . . . ?
C22 C23 C24 C27 -165.80(16) . . . . ?
C22 C23 C24 C25 -38.56(19) . . . . ?
C28 O3 C25 C26 136.11(12) . . . . ?
C28 O3 C25 C24 14.85(15) . . . . ?
O4 C24 C25 O3 -14.99(15) . . . . ?
C27 C24 C25 O3 -130.84(15) . . . . ?
C23 C24 C25 O3 102.65(15) . . . . ?
O4 C24 C25 C26 -132.18(14) . . . . ?
C27 C24 C25 C26 111.96(17) . . . . ?
C23 C24 C25 C26 -14.54(19) . . . . ?
C20 C21 C26 C25 -118.20(16) . . . . ?
C22 C21 C26 C25 -48.66(19) . . . . ?
O3 C25 C26 C21 -56.96(17) . . . . ?
C24 C25 C26 C21 58.67(18) . . . . ?
C24 O4 C28 O3 -1.58(15) . . . . ?
C24 O4 C28 C29 118.00(13) . . . . ?
C24 O4 C28 C11 -118.68(12) . . . . ?
C25 O3 C28 O4 -8.83(15) . . . . ?
C25 O3 C28 C29 -129.37(12) . . . . ?
C25 O3 C28 C11 107.94(12) . . . . ?
O2 C11 C28 O4 -179.74(10) . . . . ?
O1 C11 C28 O4 64.27(13) . . . . ?
C12 C11 C28 O4 -56.67(14) . . . . ?
O2 C11 C28 O3 63.59(13) . . . . ?
O1 C11 C28 O3 -52.40(13) . . . . ?
C12 C11 C28 O3 -173.34(11) . . . . ?
O2 C11 C28 C29 -57.29(14) . . . . ?
O1 C11 C28 C29 -173.28(11) . . . . ?
C12 C11 C28 C29 65.78(15) . . . . ?
O4 C28 C29 C34 26.54(18) . . . . ?
O3 C28 C29 C34 145.26(13) . . . . ?
C11 C28 C29 C34 -94.30(15) . . . . ?
O4 C28 C29 C30 -152.62(13) . . . . ?
O3 C28 C29 C30 -33.90(18) . . . . ?
C11 C28 C29 C30 86.54(16) . . . . ?
C34 C29 C30 C31 -0.2(3) . . . . ?
C28 C29 C30 C31 179.00(16) . . . . ?
C29 C30 C31 C32 -0.3(3) . . . . ?
C30 C31 C32 C33 0.6(3) . . . . ?
C31 C32 C33 C34 -0.5(3) . . . . ?
C30 C29 C34 C33 0.3(2) . . . . ?
C28 C29 C34 C33 -178.89(15) . . . . ?
C32 C33 C34 C29 0.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.036

data_str0165_Compound_56
_database_code_CSD               216437

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H28 O2'
_chemical_formula_weight         288.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   8.804(3)
_cell_length_b                   10.274(3)
_cell_length_c                   18.428(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1666.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9648
_exptl_absorpt_correction_T_max  0.9986
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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 SMART APEX diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14443
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_av_sigmaI/netI    0.0731
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         28.26
_reflns_number_total             3899
_reflns_number_gt                2927
_reflns_threshold_expression     I>2σ(I)

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

_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)+(0.0660P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2.1(15)
_refine_ls_number_reflns         3899
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.1220
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_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 0.15357(17) 0.16319(12) 1.03009(7) 0.0232(3) Uani 1 1 d . . .
O2 O 0.11113(18) 0.36569(12) 0.98012(7) 0.0255(4) Uani 1 1 d . . .
C1 C 0.1945(2) 0.29512(18) 1.03172(11) 0.0231(5) Uani 1 1 d . . .
H1 H 0.3054 0.3037 1.0210 0.028 Uiso 1 1 calc R . .
C2 C 0.1615(2) 0.35216(19) 1.10605(11) 0.0240(5) Uani 1 1 d . . .
C3 C 0.1508(3) 0.4863(2) 1.11330(12) 0.0298(5) Uani 1 1 d . . .
H3 H 0.1586 0.5405 1.0717 0.036 Uiso 1 1 calc R . .
C4 C 0.1287(3) 0.5414(2) 1.18130(12) 0.0359(6) Uani 1 1 d . . .
H4 H 0.1227 0.6333 1.1861 0.043 Uiso 1 1 calc R . .
C5 C 0.1156(3) 0.4637(2) 1.24170(12) 0.0392(6) Uani 1 1 d . . .
H5 H 0.0993 0.5014 1.2881 0.047 Uiso 1 1 calc R . .
C6 C 0.1262(3) 0.3299(2) 1.23427(12) 0.0384(6) Uani 1 1 d . . .
H6 H 0.1180 0.2758 1.2759 0.046 Uiso 1 1 calc R . .
C7 C 0.1488(3) 0.2744(2) 1.16671(11) 0.0306(5) Uani 1 1 d . . .
H7 H 0.1556 0.1825 1.1621 0.037 Uiso 1 1 calc R . .
C8 C 0.0462(3) 0.4146(2) 0.86171(12) 0.0386(6) Uani 1 1 d . . .
H8A H -0.0604 0.3900 0.8686 0.058 Uiso 1 1 calc R . .
H8B H 0.0732 0.4060 0.8103 0.058 Uiso 1 1 calc R . .
H8C H 0.0610 0.5050 0.8772 0.058 Uiso 1 1 calc R . .
C9 C 0.1463(3) 0.32625(18) 0.90653(10) 0.0247(5) Uani 1 1 d . . .
H9 H 0.2550 0.3473 0.8961 0.030 Uiso 1 1 calc R . .
C10 C 0.1223(2) 0.17812(18) 0.89768(10) 0.0211(4) Uani 1 1 d . . .
H10 H 0.0108 0.1600 0.8996 0.025 Uiso 1 1 calc R . .
C11 C 0.1986(2) 0.10725(19) 0.96155(10) 0.0218(4) Uani 1 1 d . . .
H11 H 0.3107 0.1203 0.9566 0.026 Uiso 1 1 calc R . .
C12 C 0.1700(2) -0.03978(19) 0.96391(11) 0.0258(5) Uani 1 1 d . . .
H12 H 0.2343 -0.0756 1.0040 0.031 Uiso 1 1 calc R . .
C13 C 0.0040(3) -0.0787(2) 0.98074(12) 0.0306(5) Uani 1 1 d . . .
H13 H -0.0639 -0.0137 0.9567 0.037 Uiso 1 1 calc R . .
C14 C -0.0400(3) -0.2141(2) 0.95222(14) 0.0440(7) Uani 1 1 d . . .
H14A H 0.0285 -0.2795 0.9728 0.066 Uiso 1 1 calc R . .
H14B H -0.0319 -0.2152 0.8992 0.066 Uiso 1 1 calc R . .
H14C H -0.1448 -0.2338 0.9665 0.066 Uiso 1 1 calc R . .
C15 C -0.0298(3) -0.0756(2) 1.06161(13) 0.0468(7) Uani 1 1 d . . .
H15A H -0.1370 -0.0965 1.0697 0.070 Uiso 1 1 calc R . .
H15B H -0.0080 0.0115 1.0807 0.070 Uiso 1 1 calc R . .
H15C H 0.0340 -0.1397 1.0865 0.070 Uiso 1 1 calc R . .
C16 C 0.2340(3) -0.0935(2) 0.89292(12) 0.0323(5) Uani 1 1 d . . .
H16A H 0.3454 -0.0805 0.8921 0.039 Uiso 1 1 calc R . .
H16B H 0.2140 -0.1882 0.8904 0.039 Uiso 1 1 calc R . .
C17 C 0.1638(3) -0.0274(2) 0.82687(11) 0.0322(5) Uani 1 1 d . . .
H17A H 0.0538 -0.0470 0.8256 0.039 Uiso 1 1 calc R . .
H17B H 0.2100 -0.0642 0.7824 0.039 Uiso 1 1 calc R . .
C18 C 0.1857(3) 0.1206(2) 0.82657(11) 0.0287(5) Uani 1 1 d . . .
H18 H 0.2974 0.1381 0.8255 0.034 Uiso 1 1 calc R . .
C19 C 0.1178(3) 0.1748(2) 0.75641(11) 0.0425(7) Uani 1 1 d . . .
H19A H 0.1532 0.1229 0.7151 0.064 Uiso 1 1 calc R . .
H19B H 0.1499 0.2654 0.7501 0.064 Uiso 1 1 calc R . .
H19C H 0.0067 0.1708 0.7590 0.064 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 1.403(2) . ?
O1 C11 1.443(2) . ?
O2 C1 1.403(2) . ?
O2 C9 1.449(2) . ?
C1 C2 1.518(3) . ?
C2 C7 1.378(3) . ?
C2 C3 1.388(3) . ?
C3 C4 1.389(3) . ?
C4 C5 1.375(3) . ?
C5 C6 1.385(3) . ?
C6 C7 1.384(3) . ?
C8 C9 1.511(3) . ?
C9 C10 1.545(3) . ?
C10 C11 1.538(3) . ?
C10 C18 1.542(3) . ?
C11 C12 1.532(3) . ?
C12 C16 1.527(3) . ?
C12 C13 1.547(3) . ?
C13 C15 1.520(3) . ?
C13 C14 1.536(3) . ?
C16 C17 1.524(3) . ?
C17 C18 1.532(3) . ?
C18 C19 1.530(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 C11 109.45(15) . . ?
C1 O2 C9 112.21(15) . . ?
O1 C1 O2 110.50(16) . . ?
O1 C1 C2 110.07(17) . . ?
O2 C1 C2 108.17(16) . . ?
C7 C2 C3 119.5(2) . . ?
C7 C2 C1 121.58(18) . . ?
C3 C2 C1 118.89(19) . . ?
C2 C3 C4 120.1(2) . . ?
C5 C4 C3 120.4(2) . . ?
C4 C5 C6 119.4(2) . . ?
C5 C6 C7 120.5(2) . . ?
C2 C7 C6 120.2(2) . . ?
O2 C9 C8 102.66(17) . . ?
O2 C9 C10 110.19(15) . . ?
C8 C9 C10 117.04(18) . . ?
C11 C10 C18 108.10(16) . . ?
C11 C10 C9 109.02(16) . . ?
C18 C10 C9 114.72(16) . . ?
O1 C11 C12 108.82(16) . . ?
O1 C11 C10 111.16(15) . . ?
C12 C11 C10 114.63(16) . . ?
C16 C12 C11 105.74(17) . . ?
C16 C12 C13 115.24(18) . . ?
C11 C12 C13 114.59(17) . . ?
C15 C13 C14 107.78(18) . . ?
C15 C13 C12 112.1(2) . . ?
C14 C13 C12 113.8(2) . . ?
C17 C16 C12 111.96(17) . . ?
C16 C17 C18 113.19(18) . . ?
C19 C18 C17 108.37(18) . . ?
C19 C18 C10 115.93(19) . . ?
C17 C18 C10 109.39(17) . . ?

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
C11 O1 C1 O2 65.9(2) . . . . ?
C11 O1 C1 C2 -174.65(15) . . . . ?
C9 O2 C1 O1 -64.9(2) . . . . ?
C9 O2 C1 C2 174.55(16) . . . . ?
O1 C1 C2 C7 21.8(3) . . . . ?
O2 C1 C2 C7 142.6(2) . . . . ?
O1 C1 C2 C3 -161.17(19) . . . . ?
O2 C1 C2 C3 -40.3(3) . . . . ?
C7 C2 C3 C4 0.5(4) . . . . ?
C1 C2 C3 C4 -176.6(2) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C3 C2 C7 C6 -0.3(4) . . . . ?
C1 C2 C7 C6 176.7(2) . . . . ?
C5 C6 C7 C2 0.3(4) . . . . ?
C1 O2 C9 C8 -179.48(17) . . . . ?
C1 O2 C9 C10 55.1(2) . . . . ?
O2 C9 C10 C11 -47.2(2) . . . . ?
C8 C9 C10 C11 -163.93(19) . . . . ?
O2 C9 C10 C18 -168.56(17) . . . . ?
C8 C9 C10 C18 74.7(3) . . . . ?
C1 O1 C11 C12 173.54(16) . . . . ?
C1 O1 C11 C10 -59.3(2) . . . . ?
C18 C10 C11 O1 175.47(15) . . . . ?
C9 C10 C11 O1 50.2(2) . . . . ?
C18 C10 C11 C12 -60.6(2) . . . . ?
C9 C10 C11 C12 174.08(17) . . . . ?
O1 C11 C12 C16 -174.77(16) . . . . ?
C10 C11 C12 C16 60.1(2) . . . . ?
O1 C11 C12 C13 57.2(2) . . . . ?
C10 C11 C12 C13 -68.0(2) . . . . ?
C16 C12 C13 C15 154.94(19) . . . . ?
C11 C12 C13 C15 -82.0(2) . . . . ?
C16 C12 C13 C14 32.3(3) . . . . ?
C11 C12 C13 C14 155.35(19) . . . . ?
C11 C12 C16 C17 -56.2(2) . . . . ?
C13 C12 C16 C17 71.5(2) . . . . ?
C12 C16 C17 C18 57.6(3) . . . . ?
C16 C17 C18 C19 177.32(19) . . . . ?
C16 C17 C18 C10 -55.4(3) . . . . ?
C11 C10 C18 C19 177.37(18) . . . . ?
C9 C10 C18 C19 -60.8(3) . . . . ?
C11 C10 C18 C17 54.5(2) . . . . ?
C9 C10 C18 C17 176.36(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.041



