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


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

loop_
_publ_author_name
'Roger Hunter'
'Philip Richards'

_publ_contact_author_name        'Prof Roger Hunter'
_publ_contact_author_address     
;
Chemistry
University of Cape Town
Rondebosch 7701
Cape Town
South Africa
7701
SOUTH AFRICA
;

_publ_contact_author_email       ROGER@SCIENCE.UCT.AC.ZA

_publ_section_title              
;
Stereoselective tetrapyrido[2,1-a]isoindolone
synthesis via carbanionic and radical intermediates:  a model study for
the Tacaman alkaloid D/E ring fusion
;

data_compound1
_database_code_CSD               208077

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
(3aS,11bS,11cR)-3a,4,5,11c-Tetrahydro-10b-hydroxy-furo-[3’,2’ :3,4]
pyrido[2,1-a]isoindol-2(1H),7(11bH)-dione
;
_chemical_name_common            
;
(3aS,11bS,11cR)-3a,4,5,11c-Tetrahydro-10b-hydroxy-furo-(3’,2’
:3,4) pyrido(2,1-a)isoindol-2(1H),7(11bH)-dione
;
_chemical_melting_point          'Mp decomposes >140C'
_chemical_formula_moiety         'C14 H13 N1 O4'
_chemical_formula_sum            'C14 H13 N1 O4'
_chemical_formula_weight         259.08

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'
N N 0.0061 0.0033 '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           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                   8.375(1)
_cell_length_b                   7.653(1)
_cell_length_c                   9.691(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.634(1)
_cell_angle_gamma                90.00
_cell_volume                     610.5(1)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9624
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_process_details   none

_exptl_special_details           
; 
? 
;

_diffrn_ambient_temperature      173(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  'NOnius Kappa CCD'
_diffrn_measurement_method       'phi- and omega-scans'
_diffrn_reflns_number            3358
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         27.39
_reflns_number_total             2511
_reflns_number_gt                2318
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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 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^)+(0.0294P)^2^+0.1067P] 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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.033(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(8)
_refine_ls_number_reflns         2511
_refine_ls_number_parameters     174
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0701
_refine_ls_wR_factor_gt          0.0675
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.280
_refine_ls_shift/su_mean         0.018

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
O19 O 0.38396(12) 0.71322(16) 0.93832(10) 0.0339(3) Uani 1 1 d . . .
N7 N 0.52683(13) 0.65221(17) 1.15833(11) 0.0239(3) Uani 1 1 d . . .
O18 O 0.68166(14) 0.42506(14) 1.28450(10) 0.0312(3) Uani 1 1 d . . .
H18 H 0.6530 0.3533 1.2190 0.037 Uiso 1 1 calc R . .
O3 O 0.69548(13) 0.89596(16) 1.53018(10) 0.0360(3) Uani 1 1 d . . .
O17 O 0.86798(14) 1.11327(18) 1.51510(13) 0.0452(3) Uani 1 1 d . . .
C10 C 0.51182(17) 0.6788(2) 1.01929(13) 0.0238(3) Uani 1 1 d . . .
C9 C 0.75368(17) 0.7093(2) 1.35448(13) 0.0249(3) Uani 1 1 d . . .
H9 H 0.8436 0.6441 1.4154 0.030 Uiso 1 1 calc R . .
C12 C 0.72814(19) 0.6792(2) 0.85966(15) 0.0305(3) Uani 1 1 d . . .
H12 H 0.6555 0.7160 0.7776 0.037 Uiso 1 1 calc R . .
C11 C 0.67622(16) 0.6558(2) 0.98597(13) 0.0244(3) Uani 1 1 d . . .
C6 C 0.39949(16) 0.6776(2) 1.24073(14) 0.0287(3) Uani 1 1 d . . .
H6A H 0.3721 0.5648 1.2805 0.034 Uiso 1 1 calc R . .
H6B H 0.3004 0.7242 1.1803 0.034 Uiso 1 1 calc R . .
C16 C 0.78121(16) 0.6052(2) 1.10711(14) 0.0252(3) Uani 1 1 d . . .
C4 C 0.62445(18) 0.7495(2) 1.44327(14) 0.0287(3) Uani 1 1 d . . .
H4 H 0.6100 0.6469 1.5037 0.034 Uiso 1 1 calc R . .
C13 C 0.8912(2) 0.6466(2) 0.85798(16) 0.0381(4) Uani 1 1 d . . .
H13 H 0.9313 0.6614 0.7732 0.046 Uiso 1 1 calc R . .
C15 C 0.94267(18) 0.5718(2) 1.10538(16) 0.0341(4) Uani 1 1 d . . .
H15 H 1.0151 0.5358 1.1878 0.041 Uiso 1 1 calc R . .
C2 C 0.80182(18) 0.9833(2) 1.46423(17) 0.0328(4) Uani 1 1 d . . .
C5 C 0.46109(18) 0.8059(2) 1.35837(16) 0.0311(3) Uani 1 1 d . . .
H5A H 0.3808 0.8146 1.4213 0.037 Uiso 1 1 calc R . .
H5B H 0.4722 0.9230 1.3178 0.037 Uiso 1 1 calc R . .
C1 C 0.81696(18) 0.8905(2) 1.32983(15) 0.0296(3) Uani 1 1 d . . .
H1A H 0.9313 0.8863 1.3166 0.036 Uiso 1 1 calc R . .
H1B H 0.7496 0.9473 1.2473 0.036 Uiso 1 1 calc R . .
C8 C 0.68891(16) 0.5937(2) 1.22810(13) 0.0234(3) Uani 1 1 d . . .
C14 C 0.9957(2) 0.5929(3) 0.97796(18) 0.0406(4) Uani 1 1 d . . .
H14 H 1.1062 0.5698 0.9736 0.049 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
O19 0.0297(5) 0.0425(7) 0.0265(5) 0.0094(5) -0.0026(4) 0.0006(5)
N7 0.0238(5) 0.0295(7) 0.0182(5) 0.0025(5) 0.0037(4) -0.0001(5)
O18 0.0490(6) 0.0237(6) 0.0195(5) 0.0006(4) 0.0025(4) 0.0010(5)
O3 0.0424(6) 0.0393(7) 0.0268(5) -0.0116(5) 0.0075(4) -0.0059(5)
O17 0.0369(6) 0.0415(8) 0.0534(7) -0.0188(6) -0.0017(5) -0.0068(5)
C10 0.0284(7) 0.0216(7) 0.0204(6) 0.0031(6) 0.0024(5) -0.0026(6)
C9 0.0291(7) 0.0264(8) 0.0177(6) -0.0013(5) 0.0002(5) 0.0029(6)
C12 0.0420(8) 0.0288(9) 0.0218(6) -0.0019(6) 0.0087(6) -0.0050(7)
C11 0.0291(7) 0.0229(8) 0.0212(6) -0.0021(6) 0.0047(5) -0.0033(6)
C6 0.0259(7) 0.0353(9) 0.0264(7) 0.0007(6) 0.0086(5) -0.0029(6)
C16 0.0286(7) 0.0249(8) 0.0219(6) -0.0046(6) 0.0046(5) -0.0004(6)
C4 0.0383(8) 0.0277(9) 0.0209(6) -0.0040(6) 0.0078(6) -0.0053(7)
C13 0.0455(9) 0.0414(11) 0.0325(8) -0.0107(8) 0.0203(7) -0.0089(8)
C15 0.0298(8) 0.0388(10) 0.0325(8) -0.0100(7) 0.0026(6) 0.0054(7)
C2 0.0277(7) 0.0345(9) 0.0337(8) -0.0059(7) -0.0012(6) 0.0020(7)
C5 0.0325(8) 0.0311(9) 0.0320(7) -0.0019(6) 0.0120(6) -0.0017(6)
C1 0.0265(7) 0.0332(9) 0.0293(7) -0.0036(7) 0.0053(6) -0.0032(6)
C8 0.0261(7) 0.0256(8) 0.0177(6) -0.0001(6) 0.0023(5) 0.0029(6)
C14 0.0323(8) 0.0498(12) 0.0430(9) -0.0157(8) 0.0157(7) -0.0014(8)

_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
O19 C10 1.2336(17) . ?
N7 C10 1.3455(16) . ?
N7 C6 1.4584(17) . ?
N7 C8 1.4702(17) . ?
O18 C8 1.4073(19) . ?
O3 C2 1.363(2) . ?
O3 C4 1.4611(18) . ?
O17 C2 1.200(2) . ?
C10 C11 1.482(2) . ?
C9 C1 1.519(2) . ?
C9 C8 1.5268(18) . ?
C9 C4 1.533(2) . ?
C12 C11 1.3842(19) . ?
C12 C13 1.391(2) . ?
C11 C16 1.3856(19) . ?
C6 C5 1.521(2) . ?
C16 C15 1.379(2) . ?
C16 C8 1.5214(19) . ?
C4 C5 1.523(2) . ?
C13 C14 1.383(3) . ?
C15 C14 1.397(2) . ?
C2 C1 1.509(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
C10 N7 C6 125.84(11) . . ?
C10 N7 C8 114.47(11) . . ?
C6 N7 C8 119.68(10) . . ?
C2 O3 C4 109.73(11) . . ?
O19 C10 N7 125.38(13) . . ?
O19 C10 C11 128.27(12) . . ?
N7 C10 C11 106.35(11) . . ?
C1 C9 C8 119.03(11) . . ?
C1 C9 C4 102.00(12) . . ?
C8 C9 C4 112.55(12) . . ?
C11 C12 C13 117.15(14) . . ?
C12 C11 C16 122.12(13) . . ?
C12 C11 C10 129.31(13) . . ?
C16 C11 C10 108.57(11) . . ?
N7 C6 C5 108.38(11) . . ?
C15 C16 C11 120.78(13) . . ?
C15 C16 C8 129.59(13) . . ?
C11 C16 C8 109.63(11) . . ?
O3 C4 C5 108.87(13) . . ?
O3 C4 C9 102.89(11) . . ?
C5 C4 C9 114.24(12) . . ?
C14 C13 C12 120.93(14) . . ?
C16 C15 C14 117.51(14) . . ?
O17 C2 O3 120.40(15) . . ?
O17 C2 C1 129.72(16) . . ?
O3 C2 C1 109.88(13) . . ?
C6 C5 C4 111.62(13) . . ?
C2 C1 C9 101.93(12) . . ?
O18 C8 N7 110.83(12) . . ?
O18 C8 C16 114.65(12) . . ?
N7 C8 C16 100.67(10) . . ?
O18 C8 C9 104.72(10) . . ?
N7 C8 C9 110.71(11) . . ?
C16 C8 C9 115.39(12) . . ?
C13 C14 C15 121.49(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
C6 N7 C10 O19 -7.1(3) . . . . ?
C8 N7 C10 O19 173.41(16) . . . . ?
C6 N7 C10 C11 173.72(14) . . . . ?
C8 N7 C10 C11 -5.80(17) . . . . ?
C13 C12 C11 C16 1.2(2) . . . . ?
C13 C12 C11 C10 -179.50(16) . . . . ?
O19 C10 C11 C12 5.1(3) . . . . ?
N7 C10 C11 C12 -175.70(15) . . . . ?
O19 C10 C11 C16 -175.50(16) . . . . ?
N7 C10 C11 C16 3.68(17) . . . . ?
C10 N7 C6 C5 -123.50(15) . . . . ?
C8 N7 C6 C5 56.00(18) . . . . ?
C12 C11 C16 C15 -1.6(2) . . . . ?
C10 C11 C16 C15 178.93(14) . . . . ?
C12 C11 C16 C8 179.05(13) . . . . ?
C10 C11 C16 C8 -0.38(17) . . . . ?
C2 O3 C4 C5 -96.32(14) . . . . ?
C2 O3 C4 C9 25.24(15) . . . . ?
C1 C9 C4 O3 -35.85(13) . . . . ?
C8 C9 C4 O3 -164.56(11) . . . . ?
C1 C9 C4 C5 81.98(15) . . . . ?
C8 C9 C4 C5 -46.73(18) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C11 C16 C15 C14 0.7(2) . . . . ?
C8 C16 C15 C14 179.88(15) . . . . ?
C4 O3 C2 O17 176.53(15) . . . . ?
C4 O3 C2 C1 -3.87(17) . . . . ?
N7 C6 C5 C4 -52.83(17) . . . . ?
O3 C4 C5 C6 166.11(11) . . . . ?
C9 C4 C5 C6 51.75(18) . . . . ?
O17 C2 C1 C9 160.28(17) . . . . ?
O3 C2 C1 C9 -19.27(15) . . . . ?
C8 C9 C1 C2 157.53(12) . . . . ?
C4 C9 C1 C2 33.04(13) . . . . ?
C10 N7 C8 O18 -116.34(13) . . . . ?
C6 N7 C8 O18 64.10(16) . . . . ?
C10 N7 C8 C16 5.37(16) . . . . ?
C6 N7 C8 C16 -174.19(13) . . . . ?
C10 N7 C8 C9 127.90(13) . . . . ?
C6 N7 C8 C9 -51.66(17) . . . . ?
C15 C16 C8 O18 -63.0(2) . . . . ?
C11 C16 C8 O18 116.26(14) . . . . ?
C15 C16 C8 N7 178.05(16) . . . . ?
C11 C16 C8 N7 -2.72(16) . . . . ?
C15 C16 C8 C9 58.9(2) . . . . ?
C11 C16 C8 C9 -121.92(14) . . . . ?
C1 C9 C8 O18 164.85(12) . . . . ?
C4 C9 C8 O18 -75.95(14) . . . . ?
C1 C9 C8 N7 -75.65(15) . . . . ?
C4 C9 C8 N7 43.54(16) . . . . ?
C1 C9 C8 C16 37.84(18) . . . . ?
C4 C9 C8 C16 157.04(13) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C16 C15 C14 C13 0.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.39
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.031