# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2002


data_global

loop_
_publ_author_name
_publ_author_address
'Sorensen, John' 
; 
Department of Chemistry
University of Alberta
Edmonton Alberta T6G 2G2
Canada
;
'Auclair, Karine' 
; 
Department of Chemistry
McGill University
Otto Maass Chemistry Building
801 Sherbrooke Street West
Montreal, Quebec H3A 2K6
Canada
;
'Kennedy, Jonathan' 
; 
Kosan Biosciences Inc.
3832 Bay Center Place
Hayward, California 94545
U. S. A.
;
'Hutchinson, C. Richard' 
; Kosan Biosciences Inc.
3832 Bay Center Place
Hayward, California 94545
U. S. A.
;
'Vederas, John C.' 
; 
Department of Chemistry
University of Alberta
Edmonton Alberta T6G 2G2
Canada
;


_publ_contact_author_name         'Dr John C. Vederas'
_publ_contact_author_address
; 
Department of Chemistry
University of Alberta
Edmonton Alberta T6G 2G2
Canada
;
_publ_contact_author_email        john.vederas@ualberta.ca
_publ_contact_author_fax          '1(780)4928231'
_publ_contact_author_phone        '1(780)4925475'
_publ_contact_letter
; To: Cambridge Crystallographic Data Centre
Please accept the following CIF data which are featured in a
manuscript being submitted to Journal of the Chemical Society,
Perkin Transactions 1.  Please forward any questions concerning
this CIF to Bob McDonald (Bob.McDonald@ualberta.ca).
;
_publ_requested_journal 'Organic & Biomolecular Chemistry'
_publ_section_title
; 
Transformations of cyclic nonaketides by Aspergillus terreus
mutants blocked for lovastatin biosynthesis at the lovA and lovC
genes
;

data_jcv9901 
_database_code_CSD                  191453

_audit_creation_method            'manual editing of SHELXL template'

_chemical_formula_sum             'C19 H30 O3' 
_chemical_formula_weight          306.43 

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    'P 21 21 21' 

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                    5.5947(9) 
_cell_length_b                    9.6504(17) 
_cell_length_c                    31.930(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      1723.9(5) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     193(2) 
_cell_measurement_reflns_used     1217 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 

_exptl_crystal_description        plate 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.28 
_exptl_crystal_size_mid           0.06 
_exptl_crystal_size_min           0.01 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.181 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              672 
_exptl_absorpt_coefficient_mu     0.078 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   0.9786 
_exptl_absorpt_correction_T_max   0.9992 
_exptl_absorpt_process_details    ? 

_diffrn_ambient_temperature       193(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type
'Bruker P4/RA diffractometer/SAMRT 1000 CCD area detector' 
_diffrn_measurement_method        '\f and \w scans' 
_diffrn_detector_area_resol_mean  8.192 
_diffrn_standards_number          0 
_diffrn_standards_interval_time   0 
_diffrn_standards_decay_%         0 
_diffrn_reflns_number             3287 
_diffrn_reflns_av_R_equivalents   0.0000 
_diffrn_reflns_av_sigmaI/netI     0.4618 
_diffrn_reflns_limit_h_min        -6 
_diffrn_reflns_limit_h_max        6 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        0 
_diffrn_reflns_limit_l_max        38 
_diffrn_reflns_theta_min          1.28 
_diffrn_reflns_theta_max          25.84 
_reflns_number_total              3287 
_reflns_number_gt                 899 
_reflns_threshold_expression      >2sigma(I) 

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

_refine_special_details 
; 
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
goodness of fit S are based on F^2^, conventional R-factors R are based 
on F, with F set to zero for negative F^2^. The threshold expression of 
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
not relevant to the choice of reflections for refinement.  R-factors based 
on F^2^ 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/[\s^2^(Fo^2^)+(0.0758P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none 
_refine_ls_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    0(5) 
_refine_ls_number_reflns          3287 
_refine_ls_number_parameters      200 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.2881 
_refine_ls_R_factor_gt            0.0620 
_refine_ls_wR_factor_ref          0.2159 
_refine_ls_wR_factor_gt           0.1103 
_refine_ls_goodness_of_fit_ref    0.779 
_refine_ls_restrained_S_all       0.779 
_refine_ls_shift/su_max           0.005 
_refine_ls_shift/su_mean          0.001 

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 0.4532(8) -0.2735(6) -0.21692(17) 0.0296(16) Uani 1 1 d . . . 
O2 O 0.7411(9) -0.3456(6) -0.25793(17) 0.0350(16) Uani 1 1 d . . . 
O3 O 0.1803(9) -0.5838(6) -0.2059(2) 0.0375(17) Uani 1 1 d . . . 
H3O H 0.2048 -0.6607 -0.2175 0.056 Uiso 1 1 calc R . . 
C1 C -0.0419(13) -0.0160(8) -0.1172(3) 0.026(2) Uani 1 1 d . . . 
H1 H 0.1052 -0.0053 -0.0997 0.031 Uiso 1 1 calc R . . 
C2 C -0.0516(12) 0.1101(9) -0.1467(2) 0.023(2) Uani 1 1 d . . . 
H2 H 0.1123 0.1220 -0.1587 0.028 Uiso 1 1 calc R . . 
C3 C -0.1076(13) 0.2406(9) -0.1222(3) 0.031(2) Uani 1 1 d . . . 
H3 H -0.0824 0.3272 -0.1357 0.038 Uiso 1 1 calc R . . 
C4 C -0.1884(14) 0.2422(9) -0.0837(3) 0.033(2) Uani 1 1 d . . . 
H4 H -0.2204 0.3293 -0.0710 0.039 Uiso 1 1 calc R . . 
C5 C -0.2323(12) 0.1150(8) -0.0591(2) 0.023(2) Uani 1 1 d . . . 
H5 H -0.0895 0.1001 -0.0408 0.027 Uiso 1 1 calc R . . 
C6 C -0.4509(12) 0.1313(9) -0.0301(3) 0.030(2) Uani 1 1 d . . . 
H6A H -0.4275 0.2127 -0.0117 0.036 Uiso 1 1 calc R . . 
H6B H -0.5953 0.1478 -0.0473 0.036 Uiso 1 1 calc R . . 
C7 C -0.4885(14) 0.0030(9) -0.0033(3) 0.031(2) Uani 1 1 d . . . 
H7 H -0.6476 0.0132 0.0106 0.037 Uiso 1 1 calc R . . 
C8 C -0.5015(13) -0.1266(9) -0.0307(3) 0.035(2) Uani 1 1 d . . . 
H8A H -0.5094 -0.2093 -0.0124 0.043 Uiso 1 1 calc R . . 
H8B H -0.6508 -0.1235 -0.0474 0.043 Uiso 1 1 calc R . . 
C9 C -0.2905(14) -0.1421(8) -0.0604(2) 0.030(2) Uani 1 1 d . . . 
H9A H -0.3178 -0.2227 -0.0790 0.035 Uiso 1 1 calc R . . 
H9B H -0.1436 -0.1600 -0.0440 0.035 Uiso 1 1 calc R . . 
C10 C -0.2554(14) -0.0114(8) -0.0872(2) 0.022(2) Uani 1 1 d . . . 
H10 H -0.4028 0.0010 -0.1045 0.026 Uiso 1 1 calc R . . 
C11 C -0.2247(13) 0.0970(8) -0.1839(2) 0.033(2) Uani 1 1 d . . . 
H11A H -0.2157 0.1808 -0.2011 0.040 Uiso 1 1 calc R . . 
H11B H -0.3881 0.0854 -0.1734 0.040 Uiso 1 1 calc R . . 
H11C H -0.1805 0.0163 -0.2009 0.040 Uiso 1 1 calc R . . 
C12 C -0.3012(15) -0.0116(9) 0.0316(3) 0.049(3) Uani 1 1 d . . . 
H12A H -0.2985 0.0732 0.0485 0.059 Uiso 1 1 calc R . . 
H12B H -0.1432 -0.0266 0.0192 0.059 Uiso 1 1 calc R . . 
H12C H -0.3423 -0.0906 0.0495 0.059 Uiso 1 1 calc R . . 
C13 C -0.0181(12) -0.1556(9) -0.1406(2) 0.028(2) Uani 1 1 d . . . 
H13A H -0.0161 -0.2323 -0.1200 0.033 Uiso 1 1 calc R . . 
H13B H -0.1582 -0.1688 -0.1591 0.033 Uiso 1 1 calc R . . 
C14 C 0.2104(13) -0.1601(8) -0.1667(2) 0.029(2) Uani 1 1 d . . . 
H14A H 0.3484 -0.1381 -0.1485 0.035 Uiso 1 1 calc R . . 
H14B H 0.2015 -0.0878 -0.1887 0.035 Uiso 1 1 calc R . . 
C15 C 0.2531(14) -0.3017(8) -0.1877(2) 0.025(2) Uani 1 1 d . . . 
H15 H 0.1079 -0.3286 -0.2041 0.030 Uiso 1 1 calc R . . 
C16 C 0.3153(14) -0.4165(8) -0.1575(2) 0.031(2) Uani 1 1 d . . . 
H16A H 0.1769 -0.4361 -0.1392 0.037 Uiso 1 1 calc R . . 
H16B H 0.4511 -0.3876 -0.1397 0.037 Uiso 1 1 calc R . . 
C17 C 0.3822(14) -0.5465(9) -0.1818(3) 0.031(3) Uani 1 1 d . . . 
H17 H 0.4237 -0.6230 -0.1620 0.037 Uiso 1 1 calc R . . 
C18 C 0.5956(13) -0.5137(9) -0.2098(3) 0.033(2) Uani 1 1 d . . . 
H18A H 0.7426 -0.5226 -0.1928 0.039 Uiso 1 1 calc R . . 
H18B H 0.6034 -0.5852 -0.2320 0.039 Uiso 1 1 calc R . . 
C19 C 0.5987(14) -0.3735(10) -0.2306(3) 0.033(3) Uani 1 1 d . . . 

loop_ 
_atom_site_aniso_label 
_atom_site_aniso_U_11 
_atom_site_aniso_U_22 
_atom_site_aniso_U_33 
_atom_site_aniso_U_23 
_atom_site_aniso_U_13 
_atom_site_aniso_U_12 
O1 0.032(3) 0.026(4) 0.031(4) 0.006(3) 0.010(3) 0.005(3) 
O2 0.035(3) 0.033(4) 0.036(4) 0.004(3) 0.013(3) 0.003(3) 
O3 0.038(3) 0.027(4) 0.048(5) -0.007(4) -0.003(3) 0.001(3) 
C1 0.034(5) 0.011(5) 0.032(6) 0.001(5) 0.000(5) 0.002(4) 
C2 0.021(4) 0.026(6) 0.023(5) -0.002(5) 0.004(4) 0.000(4) 
C3 0.040(5) 0.008(5) 0.046(7) -0.002(5) -0.005(5) -0.002(5) 
C4 0.050(6) 0.024(6) 0.025(6) 0.004(5) 0.012(5) 0.000(5) 
C5 0.024(4) 0.021(5) 0.023(5) -0.006(4) -0.001(4) 0.001(4) 
C6 0.034(5) 0.029(6) 0.026(6) -0.001(5) 0.001(4) 0.001(5) 
C7 0.031(5) 0.032(6) 0.028(6) 0.001(6) 0.007(5) 0.001(5) 
C8 0.044(5) 0.029(6) 0.033(6) 0.008(5) 0.006(5) -0.004(5) 
C9 0.050(5) 0.021(5) 0.018(5) -0.001(4) 0.008(5) 0.003(5) 
C10 0.021(4) 0.026(5) 0.017(5) 0.000(4) 0.001(4) -0.006(4) 
C11 0.044(5) 0.028(6) 0.028(6) 0.004(5) 0.003(5) 0.000(5) 
C12 0.078(6) 0.045(7) 0.024(6) -0.008(5) 0.006(6) 0.012(7) 
C13 0.026(4) 0.028(6) 0.028(6) -0.001(5) 0.004(4) -0.002(4) 
C14 0.041(5) 0.017(5) 0.029(6) 0.001(4) -0.003(5) 0.005(5) 
C15 0.025(4) 0.034(6) 0.015(5) -0.006(4) -0.005(5) 0.001(4) 
C16 0.037(5) 0.031(6) 0.023(6) 0.008(5) 0.017(5) 0.004(5) 
C17 0.030(5) 0.018(6) 0.044(7) -0.001(5) 0.002(5) 0.002(4) 
C18 0.030(4) 0.035(6) 0.034(6) -0.002(5) 0.000(4) 0.010(5) 
C19 0.021(4) 0.029(6) 0.050(7) -0.010(6) -0.013(5) 0.004(5) 

_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 C19 1.335(9) . ? 
O1 C15 1.483(9) . ? 
O2 C19 1.213(9) . ? 
O3 C17 1.414(9) . ? 
C1 C10 1.533(10) . ? 
C1 C2 1.539(11) . ? 
C1 C13 1.545(10) . ? 
C2 C3 1.515(11) . ? 
C2 C11 1.538(9) . ? 
C3 C4 1.311(10) . ? 
C4 C5 1.478(10) . ? 
C5 C10 1.520(10) . ? 
C5 C6 1.541(9) . ? 
C6 C7 1.520(11) . ? 
C7 C8 1.529(11) . ? 
C7 C12 1.537(10) . ? 
C8 C9 1.521(9) . ? 
C9 C10 1.536(10) . ? 
C13 C14 1.528(9) . ? 
C14 C15 1.541(9) . ? 
C15 C16 1.508(9) . ? 
C16 C17 1.521(10) . ? 
C17 C18 1.525(10) . ? 
C18 C19 1.507(11) . ? 

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 
C19 O1 C15 122.2(7) . . ? 
C10 C1 C2 109.4(7) . . ? 
C10 C1 C13 113.2(7) . . ? 
C2 C1 C13 113.5(7) . . ? 
C3 C2 C11 109.7(7) . . ? 
C3 C2 C1 110.5(7) . . ? 
C11 C2 C1 115.4(7) . . ? 
C4 C3 C2 124.4(9) . . ? 
C3 C4 C5 123.1(9) . . ? 
C4 C5 C10 111.5(7) . . ? 
C4 C5 C6 111.5(7) . . ? 
C10 C5 C6 111.6(7) . . ? 
C7 C6 C5 111.4(7) . . ? 
C6 C7 C8 110.5(7) . . ? 
C6 C7 C12 112.9(7) . . ? 
C8 C7 C12 112.0(7) . . ? 
C9 C8 C7 113.6(7) . . ? 
C8 C9 C10 111.4(7) . . ? 
C5 C10 C1 109.1(7) . . ? 
C5 C10 C9 110.0(6) . . ? 
C1 C10 C9 115.1(7) . . ? 
C14 C13 C1 111.1(7) . . ? 
C13 C14 C15 113.1(7) . . ? 
O1 C15 C16 111.2(6) . . ? 
O1 C15 C14 103.1(6) . . ? 
C16 C15 C14 114.2(6) . . ? 
C15 C16 C17 109.7(7) . . ? 
O3 C17 C16 106.9(6) . . ? 
O3 C17 C18 111.0(7) . . ? 
C16 C17 C18 108.7(7) . . ? 
C19 C18 C17 116.9(7) . . ? 
O2 C19 O1 118.4(9) . . ? 
O2 C19 C18 121.5(9) . . ? 
O1 C19 C18 119.9(8) . . ? 

loop_ 
_geom_torsion_atom_site_label_1 
_geom_torsion_atom_site_label_2 
_geom_torsion_atom_site_label_3 
_geom_torsion_atom_site_label_4 
_geom_torsion 
_geom_torsion_site_symmetry_1 
_geom_torsion_site_symmetry_2 
_geom_torsion_site_symmetry_3 
_geom_torsion_site_symmetry_4 
_geom_torsion_publ_flag 
C10 C1 C2 C3 45.0(8) . . . . ? 
C13 C1 C2 C3 172.5(6) . . . . ? 
C10 C1 C2 C11 -80.1(8) . . . . ? 
C13 C1 C2 C11 47.4(9) . . . . ? 
C11 C2 C3 C4 114.2(8) . . . . ? 
C1 C2 C3 C4 -14.1(11) . . . . ? 
C2 C3 C4 C5 0.8(12) . . . . ? 
C3 C4 C5 C10 -19.5(11) . . . . ? 
C3 C4 C5 C6 -145.0(7) . . . . ? 
C4 C5 C6 C7 -177.2(7) . . . . ? 
C10 C5 C6 C7 57.3(8) . . . . ? 
C5 C6 C7 C8 -53.7(9) . . . . ? 
C5 C6 C7 C12 72.6(8) . . . . ? 
C6 C7 C8 C9 52.8(9) . . . . ? 
C12 C7 C8 C9 -73.9(9) . . . . ? 
C7 C8 C9 C10 -53.7(9) . . . . ? 
C4 C5 C10 C1 50.6(8) . . . . ? 
C6 C5 C10 C1 176.0(6) . . . . ? 
C4 C5 C10 C9 177.7(6) . . . . ? 
C6 C5 C10 C9 -56.9(9) . . . . ? 
C2 C1 C10 C5 -64.8(8) . . . . ? 
C13 C1 C10 C5 167.6(7) . . . . ? 
C2 C1 C10 C9 171.1(7) . . . . ? 
C13 C1 C10 C9 43.5(9) . . . . ? 
C8 C9 C10 C5 54.7(9) . . . . ? 
C8 C9 C10 C1 178.4(6) . . . . ? 
C10 C1 C13 C14 -174.4(6) . . . . ? 
C2 C1 C13 C14 60.2(9) . . . . ? 
C1 C13 C14 C15 175.2(6) . . . . ? 
C19 O1 C15 C16 33.7(9) . . . . ? 
C19 O1 C15 C14 156.6(7) . . . . ? 
C13 C14 C15 O1 169.8(6) . . . . ? 
C13 C14 C15 C16 -69.4(9) . . . . ? 
O1 C15 C16 C17 -57.1(9) . . . . ? 
C14 C15 C16 C17 -173.3(6) . . . . ? 
C15 C16 C17 O3 -60.5(9) . . . . ? 
C15 C16 C17 C18 59.4(9) . . . . ? 
O3 C17 C18 C19 78.6(10) . . . . ? 
C16 C17 C18 C19 -38.7(10) . . . . ? 
C15 O1 C19 O2 171.9(7) . . . . ? 
C15 O1 C19 C18 -12.6(11) . . . . ? 
C17 C18 C19 O2 -169.1(7) . . . . ? 
C17 C18 C19 O1 15.6(11) . . . . ? 

_diffrn_measured_fraction_theta_max    0.991 
_diffrn_reflns_theta_full              25.84 
_diffrn_measured_fraction_theta_full   0.991 
_refine_diff_density_max    0.291 
_refine_diff_density_min   -0.310 
_refine_diff_density_rms    0.101 

#===END

data_jcv0004 
_database_code_CSD                  191454

_audit_creation_method            'manual editing of SHELXL template'


_chemical_formula_sum             'C19 H30 O4' 
_chemical_formula_weight          322.43 

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    'P 21 21 21' 

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                    5.5318(11) 
_cell_length_b                    9.7123(19) 
_cell_length_c                    32.163(7) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      1728.0(6) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     193(2) 
_cell_measurement_reflns_used     4294 
_cell_measurement_theta_min       2.450 
_cell_measurement_theta_max       26.186 

_exptl_crystal_description        plate 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.50 
_exptl_crystal_size_mid           0.39 
_exptl_crystal_size_min           0.04 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.239 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              704 
_exptl_absorpt_coefficient_mu     0.085 
_exptl_absorpt_correction_type    empirical
_exptl_absorpt_correction_T_min   0.9587 
_exptl_absorpt_correction_T_max   0.9966 
_exptl_absorpt_process_details    'SADABS (Sheldrick, 1997)' 

_diffrn_ambient_temperature       193(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 PLATFORM diffractometer/SMART 1000 CCD area detector' 
_diffrn_measurement_method        '\w scans' 
_diffrn_detector_area_resol_mean  8.192 
_diffrn_standards_number          0 
_diffrn_standards_interval_time   0 
_diffrn_standards_decay_%         0 
_diffrn_reflns_number             9765 
_diffrn_reflns_av_R_equivalents   0.0680 
_diffrn_reflns_av_sigmaI/netI     0.0747 
_diffrn_reflns_limit_h_min        -6 
_diffrn_reflns_limit_h_max        6 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -39 
_diffrn_reflns_limit_l_max        40 
_diffrn_reflns_theta_min          2.19 
_diffrn_reflns_theta_max          26.39 
_reflns_number_total              3482 
_reflns_number_gt                 2478 
_reflns_threshold_expression      >2sigma(I) 

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

_refine_special_details 
; 
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
goodness of fit S are based on F^2^, conventional R-factors R are based 
on F, with F set to zero for negative F^2^. The threshold expression of 
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
not relevant to the choice of reflections for refinement.  R-factors based 
on F^2^ 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/[\s^2^(Fo^2^)+(0.0453P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    1.5(14) 
_refine_ls_number_reflns          3482 
_refine_ls_number_parameters      209 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0885 
_refine_ls_R_factor_gt            0.0538 
_refine_ls_wR_factor_ref          0.1044 
_refine_ls_wR_factor_gt           0.0944 
_refine_ls_goodness_of_fit_ref    1.016 
_refine_ls_restrained_S_all       1.016 
_refine_ls_shift/su_max           0.002 
_refine_ls_shift/su_mean          0.001 

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 0.4497(3) 0.20875(16) 0.28165(5) 0.0292(4) Uani 1 1 d . . . 
O2 O 0.7398(3) 0.13988(17) 0.24149(5) 0.0329(4) Uani 1 1 d . . . 
O3 O 0.1860(3) -0.09667(17) 0.29272(6) 0.0351(5) Uani 1 1 d . . . 
H3O H 0.2215 -0.1661 0.2784 0.053 Uiso 1 1 calc R . . 
O4 O 0.1227(3) 0.75533(19) 0.40438(5) 0.0413(5) Uani 1 1 d . . . 
C1 C 0.6002(4) 0.1106(2) 0.26875(7) 0.0248(6) Uani 1 1 d . . . 
C2 C 0.6028(4) -0.0261(2) 0.28981(8) 0.0298(6) Uani 1 1 d . . . 
H2A H 0.7508 -0.0319 0.3070 0.036 Uiso 1 1 calc R . . 
H2B H 0.6144 -0.0984 0.2682 0.036 Uiso 1 1 calc R . . 
C3 C 0.3879(4) -0.0579(2) 0.31711(7) 0.0269(6) Uani 1 1 d . . . 
H3 H 0.4297 -0.1336 0.3369 0.032 Uiso 1 1 calc R . . 
C4 C 0.3168(4) 0.0688(2) 0.34088(7) 0.0293(6) Uani 1 1 d . . . 
H4A H 0.4522 0.0980 0.3590 0.035 Uiso 1 1 calc R . . 
H4B H 0.1760 0.0479 0.3588 0.035 Uiso 1 1 calc R . . 
C5 C 0.2533(4) 0.1835(2) 0.31131(7) 0.0255(6) Uani 1 1 d . . . 
H5 H 0.1045 0.1572 0.2955 0.031 Uiso 1 1 calc R . . 
C6 C 0.2133(4) 0.3230(2) 0.33121(7) 0.0303(6) Uani 1 1 d . . . 
H6A H 0.1958 0.3926 0.3089 0.036 Uiso 1 1 calc R . . 
H6B H 0.3587 0.3472 0.3476 0.036 Uiso 1 1 calc R . . 
C7 C -0.0067(4) 0.3312(2) 0.35950(7) 0.0258(6) Uani 1 1 d . . . 
H7A H 0.0029 0.2574 0.3807 0.031 Uiso 1 1 calc R . . 
H7B H -0.1548 0.3159 0.3428 0.031 Uiso 1 1 calc R . . 
C8 C -0.0239(4) 0.4710(2) 0.38132(7) 0.0210(5) Uani 1 1 d . . . 
H8 H 0.1298 0.4821 0.3974 0.025 Uiso 1 1 calc R . . 
C9 C -0.0336(4) 0.5926(2) 0.35056(7) 0.0239(5) Uani 1 1 d . . . 
H9 H 0.1238 0.5939 0.3353 0.029 Uiso 1 1 calc R . . 
C10 C -0.0550(4) 0.7273(3) 0.37302(7) 0.0295(6) Uani 1 1 d . . . 
H10 H -0.1027 0.8078 0.3554 0.035 Uiso 1 1 calc R . . 
C11 C -0.1272(5) 0.7351(3) 0.41639(8) 0.0318(6) Uani 1 1 d . . . 
H11 H -0.2175 0.8200 0.4247 0.038 Uiso 1 1 calc R . . 
C12 C -0.1822(4) 0.6077(2) 0.44125(7) 0.0257(6) Uani 1 1 d . . . 
H12 H -0.0350 0.5863 0.4581 0.031 Uiso 1 1 calc R . . 
C13 C -0.3889(5) 0.6310(3) 0.47166(8) 0.0320(6) Uani 1 1 d . . . 
H13A H -0.5370 0.6546 0.4559 0.038 Uiso 1 1 calc R . . 
H13B H -0.3491 0.7101 0.4898 0.038 Uiso 1 1 calc R . . 
C14 C -0.4385(5) 0.5051(3) 0.49858(8) 0.0339(7) Uani 1 1 d . . . 
H14 H -0.5939 0.5218 0.5136 0.041 Uiso 1 1 calc R . . 
C15 C -0.4748(5) 0.3795(3) 0.47093(8) 0.0347(6) Uani 1 1 d . . . 
H15A H -0.4889 0.2968 0.4888 0.042 Uiso 1 1 calc R . . 
H15B H -0.6290 0.3900 0.4556 0.042 Uiso 1 1 calc R . . 
C16 C -0.2725(4) 0.3568(2) 0.43978(7) 0.0283(6) Uani 1 1 d . . . 
H16A H -0.1219 0.3336 0.4549 0.034 Uiso 1 1 calc R . . 
H16B H -0.3141 0.2779 0.4217 0.034 Uiso 1 1 calc R . . 
C17 C -0.2294(4) 0.4832(2) 0.41306(7) 0.0214(5) Uani 1 1 d . . . 
H17 H -0.3817 0.5018 0.3973 0.026 Uiso 1 1 calc R . . 
C18 C -0.2325(4) 0.5824(3) 0.31812(7) 0.0337(6) Uani 1 1 d . . . 
H18A H -0.2268 0.6635 0.3000 0.040 Uiso 1 1 calc R . . 
H18B H -0.3900 0.5782 0.3320 0.040 Uiso 1 1 calc R . . 
H18C H -0.2089 0.4991 0.3014 0.040 Uiso 1 1 calc R . . 
C19 C -0.2438(6) 0.4817(3) 0.53118(8) 0.0444(7) Uani 1 1 d . . . 
H19A H -0.2287 0.5640 0.5486 0.053 Uiso 1 1 calc R . . 
H19B H -0.0892 0.4633 0.5174 0.053 Uiso 1 1 calc R . . 
H19C H -0.2880 0.4027 0.5486 0.053 Uiso 1 1 calc R . . 

loop_ 
_atom_site_aniso_label 
_atom_site_aniso_U_11 
_atom_site_aniso_U_22 
_atom_site_aniso_U_33 
_atom_site_aniso_U_23 
_atom_site_aniso_U_13 
_atom_site_aniso_U_12 
O1 0.0312(10) 0.0189(9) 0.0374(10) 0.0023(8) 0.0118(8) 0.0057(7) 
O2 0.0301(10) 0.0293(10) 0.0392(10) 0.0035(8) 0.0111(9) 0.0017(8) 
O3 0.0279(10) 0.0217(10) 0.0557(12) -0.0098(9) 0.0018(9) 0.0000(8) 
O4 0.0427(11) 0.0353(12) 0.0457(11) -0.0067(10) -0.0007(10) -0.0151(9) 
C1 0.0204(12) 0.0242(14) 0.0297(13) -0.0012(12) 0.0007(12) 0.0010(11) 
C2 0.0265(13) 0.0223(14) 0.0406(15) 0.0016(13) 0.0013(12) 0.0035(11) 
C3 0.0274(13) 0.0189(14) 0.0345(14) 0.0042(12) 0.0006(12) 0.0011(10) 
C4 0.0338(15) 0.0254(15) 0.0286(13) 0.0011(12) 0.0042(12) -0.0015(11) 
C5 0.0243(13) 0.0232(14) 0.0290(13) -0.0044(11) 0.0068(11) 0.0008(11) 
C6 0.0348(15) 0.0201(14) 0.0361(15) -0.0025(12) 0.0055(12) 0.0013(11) 
C7 0.0311(14) 0.0180(13) 0.0282(13) -0.0019(11) 0.0060(11) 0.0020(11) 
C8 0.0198(12) 0.0185(13) 0.0247(12) -0.0022(11) 0.0002(10) 0.0006(10) 
C9 0.0240(13) 0.0208(13) 0.0270(13) 0.0008(11) 0.0045(11) -0.0018(11) 
C10 0.0341(15) 0.0200(14) 0.0345(14) 0.0017(12) -0.0004(12) -0.0026(12) 
C11 0.0356(15) 0.0179(14) 0.0418(16) -0.0060(12) 0.0003(13) 0.0029(11) 
C12 0.0262(13) 0.0207(14) 0.0302(13) -0.0012(12) -0.0015(11) 0.0007(11) 
C13 0.0382(15) 0.0251(15) 0.0327(14) -0.0059(12) 0.0040(13) 0.0049(12) 
C14 0.0386(16) 0.0320(16) 0.0312(14) -0.0014(12) 0.0114(13) 0.0030(12) 
C15 0.0400(16) 0.0305(16) 0.0336(14) 0.0018(12) 0.0073(13) -0.0047(13) 
C16 0.0364(15) 0.0197(14) 0.0287(13) -0.0018(11) 0.0050(12) -0.0024(12) 
C17 0.0235(13) 0.0177(13) 0.0229(12) -0.0029(10) -0.0017(11) -0.0003(10) 
C18 0.0366(15) 0.0300(16) 0.0345(14) 0.0028(12) -0.0018(13) 0.0013(12) 
C19 0.071(2) 0.0304(17) 0.0319(15) -0.0018(13) 0.0040(16) 0.0045(15) 

_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 1.332(3) . ? 
O1 C5 1.466(3) . ? 
O2 C1 1.203(3) . ? 
O3 C3 1.416(3) . ? 
O4 C10 1.434(3) . ? 
O4 C11 1.449(3) . ? 
C1 C2 1.490(3) . ? 
C2 C3 1.510(3) . ? 
C3 C4 1.501(3) . ? 
C4 C5 1.506(3) . ? 
C5 C6 1.515(3) . ? 
C6 C7 1.521(3) . ? 
C7 C8 1.531(3) . ? 
C8 C17 1.532(3) . ? 
C8 C9 1.541(3) . ? 
C9 C10 1.500(3) . ? 
C9 C18 1.519(3) . ? 
C10 C11 1.453(3) . ? 
C11 C12 1.504(3) . ? 
C12 C13 1.522(3) . ? 
C12 C17 1.534(3) . ? 
C13 C14 1.524(3) . ? 
C14 C19 1.520(4) . ? 
C14 C15 1.523(3) . ? 
C15 C16 1.518(3) . ? 
C16 C17 1.517(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 C5 123.10(18) . . ? 
C10 O4 C11 60.52(15) . . ? 
O2 C1 O1 117.4(2) . . ? 
O2 C1 C2 122.4(2) . . ? 
O1 C1 C2 120.1(2) . . ? 
C1 C2 C3 116.0(2) . . ? 
O3 C3 C4 107.07(19) . . ? 
O3 C3 C2 110.71(19) . . ? 
C4 C3 C2 109.6(2) . . ? 
C3 C4 C5 110.2(2) . . ? 
O1 C5 C4 111.20(19) . . ? 
O1 C5 C6 103.52(18) . . ? 
C4 C5 C6 115.4(2) . . ? 
C5 C6 C7 114.6(2) . . ? 
C6 C7 C8 111.74(19) . . ? 
C7 C8 C17 114.82(18) . . ? 
C7 C8 C9 112.77(18) . . ? 
C17 C8 C9 110.03(19) . . ? 
C10 C9 C18 109.3(2) . . ? 
C10 C9 C8 111.22(18) . . ? 
C18 C9 C8 114.6(2) . . ? 
O4 C10 C11 60.23(15) . . ? 
O4 C10 C9 116.8(2) . . ? 
C11 C10 C9 122.0(2) . . ? 
O4 C11 C10 59.25(15) . . ? 
O4 C11 C12 116.5(2) . . ? 
C10 C11 C12 121.6(2) . . ? 
C11 C12 C13 111.8(2) . . ? 
C11 C12 C17 111.62(19) . . ? 
C13 C12 C17 111.66(19) . . ? 
C12 C13 C14 112.4(2) . . ? 
C19 C14 C15 112.1(2) . . ? 
C19 C14 C13 112.6(2) . . ? 
C15 C14 C13 109.6(2) . . ? 
C16 C15 C14 113.9(2) . . ? 
C17 C16 C15 111.8(2) . . ? 
C16 C17 C8 115.56(19) . . ? 
C16 C17 C12 109.26(18) . . ? 
C8 C17 C12 109.16(18) . . ? 

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 
C5 O1 C1 O2 173.14(19) . . . . ? 
C5 O1 C1 C2 -10.9(3) . . . . ? 
O2 C1 C2 C3 -168.3(2) . . . . ? 
O1 C1 C2 C3 16.0(3) . . . . ? 
C1 C2 C3 O3 77.8(3) . . . . ? 
C1 C2 C3 C4 -40.1(3) . . . . ? 
O3 C3 C4 C5 -60.8(3) . . . . ? 
C2 C3 C4 C5 59.4(3) . . . . ? 
C1 O1 C5 C4 30.1(3) . . . . ? 
C1 O1 C5 C6 154.6(2) . . . . ? 
C3 C4 C5 O1 -54.1(3) . . . . ? 
C3 C4 C5 C6 -171.5(2) . . . . ? 
O1 C5 C6 C7 172.04(18) . . . . ? 
C4 C5 C6 C7 -66.2(3) . . . . ? 
C5 C6 C7 C8 175.2(2) . . . . ? 
C6 C7 C8 C17 -175.29(18) . . . . ? 
C6 C7 C8 C9 57.6(3) . . . . ? 
C7 C8 C9 C10 178.94(19) . . . . ? 
C17 C8 C9 C10 49.3(2) . . . . ? 
C7 C8 C9 C18 54.4(3) . . . . ? 
C17 C8 C9 C18 -75.3(2) . . . . ? 
C11 O4 C10 C9 -113.2(2) . . . . ? 
C18 C9 C10 O4 -178.79(19) . . . . ? 
C8 C9 C10 O4 53.7(3) . . . . ? 
C18 C9 C10 C11 111.1(3) . . . . ? 
C8 C9 C10 C11 -16.4(3) . . . . ? 
C10 O4 C11 C12 112.6(2) . . . . ? 
C9 C10 C11 O4 104.7(2) . . . . ? 
O4 C10 C11 C12 -104.1(2) . . . . ? 
C9 C10 C11 C12 0.6(4) . . . . ? 
O4 C11 C12 C13 147.7(2) . . . . ? 
C10 C11 C12 C13 -143.6(2) . . . . ? 
O4 C11 C12 C17 -86.4(2) . . . . ? 
C10 C11 C12 C17 -17.7(3) . . . . ? 
C11 C12 C13 C14 -177.2(2) . . . . ? 
C17 C12 C13 C14 57.0(3) . . . . ? 
C12 C13 C14 C19 72.4(3) . . . . ? 
C12 C13 C14 C15 -53.1(3) . . . . ? 
C19 C14 C15 C16 -73.4(3) . . . . ? 
C13 C14 C15 C16 52.4(3) . . . . ? 
C14 C15 C16 C17 -54.9(3) . . . . ? 
C15 C16 C17 C8 178.60(19) . . . . ? 
C15 C16 C17 C12 55.1(3) . . . . ? 
C7 C8 C17 C16 39.8(3) . . . . ? 
C9 C8 C17 C16 168.30(19) . . . . ? 
C7 C8 C17 C12 163.40(19) . . . . ? 
C9 C8 C17 C12 -68.1(2) . . . . ? 
C11 C12 C17 C16 177.5(2) . . . . ? 
C13 C12 C17 C16 -56.6(3) . . . . ? 
C11 C12 C17 C8 50.2(2) . . . . ? 
C13 C12 C17 C8 176.20(18) . . . . ? 

_diffrn_measured_fraction_theta_max    0.993 
_diffrn_reflns_theta_full              26.39 
_diffrn_measured_fraction_theta_full   0.993 
_refine_diff_density_max    0.217 
_refine_diff_density_min   -0.161 
_refine_diff_density_rms    0.042 

#===END