# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2003


data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'John C. Vederas'
'John L. Sorensen'

_publ_contact_author_name        '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_phone       780-492-5475
_publ_contact_author_fax         780-492-8231

_publ_requested_journal          'Chemical Communications'

_publ_section_title              
;
Monacolin N, a compound resulting from derailment
of type I iterative polyketide synthase function enroute to lovastatin
;

data_jcv0302
_database_code_CSD               208957

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H28 O3'
_chemical_formula_weight         304.41

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                   5.5364(8)
_cell_length_b                   9.9736(14)
_cell_length_c                   31.173(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1721.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    2396
_cell_measurement_theta_min      2.424
_cell_measurement_theta_max      23.315

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9682
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
;
?
;

_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            8084
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0535
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         1.31
_diffrn_reflns_theta_max         26.35
_reflns_number_total             3504
_reflns_number_gt                2789
_reflns_threshold_expression     I>2\s(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    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL (Bruker, 1997)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 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^)+(0.0532P)^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   1.2(14)
_refine_ls_number_reflns         3504
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1111
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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 0.4623(2) 0.23726(13) -0.20902(4) 0.0286(4) Uani 1 1 d . . .
O2 O 0.7472(3) 0.18629(14) -0.25431(5) 0.0355(4) Uani 1 1 d . . .
O3 O 0.1751(2) -0.06454(14) -0.20828(5) 0.0323(4) Uani 1 1 d . . .
H3O H 0.1869 -0.1386 -0.2210 0.039 Uiso 1 1 calc R . .
C1 C 0.6042(4) 0.1462(2) -0.22785(6) 0.0251(5) Uani 1 1 d . . .
C2 C 0.5958(3) 0.0023(2) -0.21448(7) 0.0279(5) Uani 1 1 d . . .
H2A H 0.7503 -0.0195 -0.2001 0.033 Uiso 1 1 calc R . .
H2B H 0.5863 -0.0534 -0.2407 0.033 Uiso 1 1 calc R . .
C3 C 0.3908(4) -0.0390(2) -0.18485(7) 0.0268(5) Uani 1 1 d . . .
H3 H 0.4381 -0.1208 -0.1683 0.032 Uiso 1 1 calc R . .
C4 C 0.3363(4) 0.0740(2) -0.15443(7) 0.0289(5) Uani 1 1 d . . .
H4A H 0.4801 0.0925 -0.1365 0.035 Uiso 1 1 calc R . .
H4B H 0.2021 0.0478 -0.1352 0.035 Uiso 1 1 calc R . .
C5 C 0.2671(4) 0.19951(19) -0.17896(6) 0.0246(5) Uani 1 1 d . . .
H5 H 0.1162 0.1816 -0.1956 0.030 Uiso 1 1 calc R . .
C6 C 0.2296(4) 0.31965(19) -0.15155(6) 0.0271(5) Uani 1 1 d . . .
H6 H 0.3627 0.3492 -0.1348 0.032 Uiso 1 1 calc R . .
C7 C 0.0276(4) 0.3884(2) -0.14855(6) 0.0245(5) Uani 1 1 d . . .
H7 H -0.1073 0.3580 -0.1647 0.029 Uiso 1 1 calc R . .
C8 C -0.0049(3) 0.51175(19) -0.12142(6) 0.0233(4) Uani 1 1 d . . .
H8 H 0.1473 0.5239 -0.1046 0.028 Uiso 1 1 calc R . .
C9 C -0.0362(4) 0.6384(2) -0.14959(7) 0.0261(5) Uani 1 1 d . . .
H9 H 0.1244 0.6585 -0.1628 0.031 Uiso 1 1 calc R . .
C10 C -0.1036(4) 0.7566(2) -0.12221(7) 0.0318(5) Uani 1 1 d . . .
H10 H -0.0922 0.8432 -0.1348 0.038 Uiso 1 1 calc R . .
C11 C -0.1772(4) 0.7494(2) -0.08212(7) 0.0302(5) Uani 1 1 d . . .
H11 H -0.2168 0.8305 -0.0677 0.036 Uiso 1 1 calc R . .
C12 C -0.2018(4) 0.6202(2) -0.05791(6) 0.0254(5) Uani 1 1 d . . .
H12 H -0.0536 0.6093 -0.0399 0.030 Uiso 1 1 calc R . .
C13 C -0.4198(4) 0.6191(2) -0.02768(7) 0.0319(5) Uani 1 1 d . . .
H13A H -0.4073 0.6958 -0.0076 0.038 Uiso 1 1 calc R . .
H13B H -0.5693 0.6307 -0.0447 0.038 Uiso 1 1 calc R . .
C14 C -0.4375(4) 0.4892(2) -0.00194(7) 0.0369(6) Uani 1 1 d . . .
H14 H -0.5993 0.4887 0.0123 0.044 Uiso 1 1 calc R . .
C15 C -0.4293(4) 0.3680(2) -0.03200(7) 0.0357(5) Uani 1 1 d . . .
H15A H -0.4197 0.2853 -0.0145 0.043 Uiso 1 1 calc R . .
H15B H -0.5816 0.3645 -0.0486 0.043 Uiso 1 1 calc R . .
C16 C -0.2166(4) 0.3705(2) -0.06329(7) 0.0309(5) Uani 1 1 d . . .
H16A H -0.0636 0.3614 -0.0471 0.037 Uiso 1 1 calc R . .
H16B H -0.2294 0.2935 -0.0832 0.037 Uiso 1 1 calc R . .
C17 C -0.2127(4) 0.50073(19) -0.08892(6) 0.0221(4) Uani 1 1 d . . .
H17 H -0.3681 0.5069 -0.1052 0.027 Uiso 1 1 calc R . .
C18 C -0.2180(4) 0.6228(2) -0.18631(7) 0.0339(5) Uani 1 1 d . . .
H18A H -0.2299 0.7074 -0.2022 0.041 Uiso 1 1 calc R . .
H18B H -0.3766 0.5994 -0.1746 0.041 Uiso 1 1 calc R . .
H18C H -0.1637 0.5516 -0.2057 0.041 Uiso 1 1 calc R . .
C19 C -0.2482(5) 0.4810(3) 0.03330(7) 0.0495(7) Uani 1 1 d . . .
H19A H -0.2572 0.5615 0.0513 0.059 Uiso 1 1 calc R . .
H19B H -0.0872 0.4747 0.0204 0.059 Uiso 1 1 calc R . .
H19C H -0.2782 0.4015 0.0510 0.059 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 0.0322(8) 0.0217(7) 0.0320(8) 0.0014(7) 0.0099(7) 0.0035(6)
O2 0.0358(9) 0.0324(8) 0.0384(9) 0.0059(7) 0.0132(8) 0.0018(8)
O3 0.0248(7) 0.0241(8) 0.0478(10) -0.0093(8) 0.0009(7) -0.0007(6)
C1 0.0235(10) 0.0261(11) 0.0258(11) -0.0004(9) -0.0016(9) 0.0026(9)
C2 0.0235(10) 0.0213(10) 0.0389(13) -0.0021(11) 0.0035(10) 0.0035(9)
C3 0.0273(10) 0.0190(11) 0.0341(12) 0.0051(10) -0.0010(10) 0.0021(9)
C4 0.0320(11) 0.0282(11) 0.0266(11) 0.0007(10) 0.0033(10) -0.0013(9)
C5 0.0222(10) 0.0259(11) 0.0259(11) -0.0024(9) 0.0037(9) 0.0010(9)
C6 0.0275(11) 0.0272(10) 0.0264(11) -0.0066(9) -0.0015(9) -0.0014(10)
C7 0.0246(10) 0.0258(11) 0.0231(11) -0.0019(9) 0.0023(9) -0.0028(9)
C8 0.0201(9) 0.0250(11) 0.0248(11) -0.0048(9) -0.0005(8) -0.0001(9)
C9 0.0260(10) 0.0248(11) 0.0275(11) 0.0008(9) 0.0042(9) -0.0022(9)
C10 0.0373(12) 0.0191(11) 0.0391(13) 0.0031(10) 0.0006(11) -0.0027(10)
C11 0.0348(11) 0.0198(10) 0.0359(13) -0.0075(10) 0.0001(10) 0.0018(10)
C12 0.0250(10) 0.0269(10) 0.0243(11) -0.0047(9) -0.0011(9) -0.0002(9)
C13 0.0322(12) 0.0352(12) 0.0283(12) -0.0104(11) 0.0025(10) 0.0036(10)
C14 0.0360(12) 0.0441(14) 0.0307(12) 0.0003(11) 0.0097(10) 0.0003(12)
C15 0.0416(13) 0.0329(12) 0.0327(13) 0.0034(11) 0.0050(11) -0.0058(11)
C16 0.0388(12) 0.0258(11) 0.0281(12) -0.0012(10) 0.0034(10) 0.0007(10)
C17 0.0235(9) 0.0207(9) 0.0222(10) -0.0043(9) 0.0011(8) 0.0003(9)
C18 0.0388(12) 0.0340(12) 0.0289(12) 0.0022(10) 0.0017(11) 0.0024(11)
C19 0.0687(17) 0.0524(15) 0.0272(13) -0.0006(12) 0.0025(13) 0.0044(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 1.337(2) . ?
O1 C5 1.479(2) . ?
O2 C1 1.211(2) . ?
O3 C3 1.423(2) . ?
C1 C2 1.495(3) . ?
C2 C3 1.520(3) . ?
C3 C4 1.504(3) . ?
C4 C5 1.516(3) . ?
C5 C6 1.486(3) . ?
C6 C7 1.315(3) . ?
C7 C8 1.503(3) . ?
C8 C17 1.537(3) . ?
C8 C9 1.548(3) . ?
C9 C10 1.503(3) . ?
C9 C18 1.532(3) . ?
C10 C11 1.317(3) . ?
C11 C12 1.500(3) . ?
C12 C13 1.531(3) . ?
C12 C17 1.536(3) . ?
C13 C14 1.527(3) . ?
C14 C19 1.521(3) . ?
C14 C15 1.530(3) . ?
C15 C16 1.529(3) . ?
C16 C17 1.525(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 122.33(15) . . ?
O2 C1 O1 117.34(18) . . ?
O2 C1 C2 121.80(19) . . ?
O1 C1 C2 120.75(18) . . ?
C1 C2 C3 116.91(17) . . ?
O3 C3 C4 106.83(16) . . ?
O3 C3 C2 111.29(17) . . ?
C4 C3 C2 109.26(17) . . ?
C3 C4 C5 110.58(17) . . ?
O1 C5 C6 105.12(15) . . ?
O1 C5 C4 110.19(15) . . ?
C6 C5 C4 114.25(17) . . ?
C7 C6 C5 125.4(2) . . ?
C6 C7 C8 124.65(19) . . ?
C7 C8 C17 113.70(16) . . ?
C7 C8 C9 111.23(16) . . ?
C17 C8 C9 110.39(16) . . ?
C10 C9 C18 109.94(17) . . ?
C10 C9 C8 110.24(16) . . ?
C18 C9 C8 114.48(17) . . ?
C11 C10 C9 125.0(2) . . ?
C10 C11 C12 123.6(2) . . ?
C11 C12 C13 112.80(17) . . ?
C11 C12 C17 110.71(16) . . ?
C13 C12 C17 110.54(17) . . ?
C14 C13 C12 112.33(17) . . ?
C19 C14 C13 112.4(2) . . ?
C19 C14 C15 112.3(2) . . ?
C13 C14 C15 110.28(17) . . ?
C16 C15 C14 113.61(19) . . ?
C17 C16 C15 111.02(18) . . ?
C16 C17 C12 109.38(15) . . ?
C16 C17 C8 114.62(17) . . ?
C12 C17 C8 109.27(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
C5 O1 C1 O2 174.75(18) . . . . ?
C5 O1 C1 C2 -9.0(3) . . . . ?
O2 C1 C2 C3 -173.33(19) . . . . ?
O1 C1 C2 C3 10.6(3) . . . . ?
C1 C2 C3 O3 82.4(2) . . . . ?
C1 C2 C3 C4 -35.3(2) . . . . ?
O3 C3 C4 C5 -61.7(2) . . . . ?
C2 C3 C4 C5 58.8(2) . . . . ?
C1 O1 C5 C6 155.57(17) . . . . ?
C1 O1 C5 C4 32.0(2) . . . . ?
C3 C4 C5 O1 -57.2(2) . . . . ?
C3 C4 C5 C6 -175.23(17) . . . . ?
O1 C5 C6 C7 119.1(2) . . . . ?
C4 C5 C6 C7 -120.0(2) . . . . ?
C5 C6 C7 C8 -178.45(18) . . . . ?
C6 C7 C8 C17 -123.7(2) . . . . ?
C6 C7 C8 C9 111.0(2) . . . . ?
C7 C8 C9 C10 171.92(16) . . . . ?
C17 C8 C9 C10 44.7(2) . . . . ?
C7 C8 C9 C18 47.4(2) . . . . ?
C17 C8 C9 C18 -79.8(2) . . . . ?
C18 C9 C10 C11 113.3(2) . . . . ?
C8 C9 C10 C11 -13.8(3) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C11 C12 C13 -143.1(2) . . . . ?
C10 C11 C12 C17 -18.6(3) . . . . ?
C11 C12 C13 C14 -177.79(18) . . . . ?
C17 C12 C13 C14 57.7(2) . . . . ?
C12 C13 C14 C19 73.5(2) . . . . ?
C12 C13 C14 C15 -52.7(2) . . . . ?
C19 C14 C15 C16 -74.9(2) . . . . ?
C13 C14 C15 C16 51.3(3) . . . . ?
C14 C15 C16 C17 -54.6(3) . . . . ?
C15 C16 C17 C12 57.2(2) . . . . ?
C15 C16 C17 C8 -179.75(17) . . . . ?
C11 C12 C17 C16 175.33(17) . . . . ?
C13 C12 C17 C16 -58.9(2) . . . . ?
C11 C12 C17 C8 49.1(2) . . . . ?
C13 C12 C17 C8 174.84(16) . . . . ?
C7 C8 C17 C16 47.0(2) . . . . ?
C9 C8 C17 C16 172.77(17) . . . . ?
C7 C8 C17 C12 170.12(16) . . . . ?
C9 C8 C17 C12 -64.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.35
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.088