# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009

data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'David Spring'
'Monica Diaz-Gavilan'
'Warren R. J. D Galloway'
'James T. Hodkingson'
"Kieron M. G. O'Connell"

_publ_contact_author_name        'David Spring'
_publ_contact_author_email       DRSPRING@CH.CAM.AC.UK

_publ_section_title              
;
Diversity-oriented synthesis of bicyclic and tricyclic alkaloids
;

# Attachment 'DS0802.cif'

data_ds0802
_database_code_depnum_ccdc_archive 'CCDC 746888'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H23 N O3'
_chemical_formula_sum            'C15 H23 N O3'
_chemical_formula_weight         265.34

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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6717(2)
_cell_length_b                   8.8865(2)
_cell_length_c                   9.6551(2)
_cell_angle_alpha                86.555(1)
_cell_angle_beta                 72.478(1)
_cell_angle_gamma                80.643(1)
_cell_volume                     700.02(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    8450
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      30.03

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;

_exptl_special_details           
;
No unusual crystallographic features.
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice \w and \f scans'
_diffrn_reflns_number            12361
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.66
_diffrn_reflns_theta_max         30.04
_reflns_number_total             4060
_reflns_number_gt                3390
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (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^)+(0.0449P)^2^+0.1948P] 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_number_reflns         4060
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.1107
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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
N1 N 0.22644(10) 0.98002(9) 0.80516(8) 0.02209(17) Uani 1 1 d . . .
O1 O 0.46049(10) 0.67480(10) 0.44850(9) 0.03350(19) Uani 1 1 d . . .
O2 O 0.25095(16) 0.98486(11) 0.37580(10) 0.0549(3) Uani 1 1 d . . .
O3 O 0.21218(9) 0.63276(9) 0.44790(8) 0.03056(18) Uani 1 1 d . . .
C1 C 0.31367(13) 0.70564(12) 0.49012(11) 0.0260(2) Uani 1 1 d . . .
C2 C 0.22059(12) 0.83395(11) 0.59392(11) 0.0253(2) Uani 1 1 d . . .
H2 H 0.1063 0.8126 0.6391 0.030 Uiso 1 1 calc R . .
C3 C 0.21304(15) 0.98190(13) 0.50694(12) 0.0326(2) Uani 1 1 d . . .
C4 C 0.15540(16) 1.12051(13) 0.59956(13) 0.0353(3) Uani 1 1 d . . .
H4A H 0.0370 1.1260 0.6503 0.042 Uiso 1 1 calc R . .
H4B H 0.1712 1.2127 0.5372 0.042 Uiso 1 1 calc R . .
C5 C 0.24847(13) 1.11780(11) 0.71174(11) 0.0257(2) Uani 1 1 d . . .
H5 H 0.3676 1.1148 0.6596 0.031 Uiso 1 1 calc R . .
C6 C 0.18590(14) 1.26493(12) 0.79834(12) 0.0313(2) Uani 1 1 d . . .
H6A H 0.2100 1.3531 0.7320 0.038 Uiso 1 1 calc R . .
H6B H 0.0657 1.2744 0.8407 0.038 Uiso 1 1 calc R . .
C7 C 0.26314(17) 1.26934(13) 0.91908(14) 0.0371(3) Uani 1 1 d . . .
H7A H 0.2115 1.3608 0.9792 0.045 Uiso 1 1 calc R . .
H7B H 0.3814 1.2744 0.8774 0.045 Uiso 1 1 calc R . .
C8 C 0.23871(15) 1.12613(13) 1.01192(12) 0.0327(2) Uani 1 1 d . . .
H8A H 0.1205 1.1271 1.0607 0.039 Uiso 1 1 calc R . .
H8B H 0.2941 1.1249 1.0880 0.039 Uiso 1 1 calc R . .
C9 C 0.30696(12) 0.98269(11) 0.92087(10) 0.0245(2) Uani 1 1 d . . .
H9 H 0.4266 0.9826 0.8735 0.029 Uiso 1 1 calc R . .
C10 C 0.28541(14) 0.84219(12) 1.01905(11) 0.0304(2) Uani 1 1 d . . .
H10A H 0.3410 0.8461 1.0943 0.036 Uiso 1 1 calc R . .
H10B H 0.1675 0.8421 1.0688 0.036 Uiso 1 1 calc R . .
C11 C 0.35572(15) 0.69604(12) 0.93298(12) 0.0327(2) Uani 1 1 d . . .
H11A H 0.4760 0.6892 0.8927 0.039 Uiso 1 1 calc R . .
H11B H 0.3316 0.6065 0.9973 0.039 Uiso 1 1 calc R . .
C12 C 0.27939(14) 0.69707(11) 0.81016(11) 0.0284(2) Uani 1 1 d . . .
H12A H 0.1615 0.6902 0.8515 0.034 Uiso 1 1 calc R . .
H12B H 0.3317 0.6067 0.7486 0.034 Uiso 1 1 calc R . .
C13 C 0.29959(12) 0.84175(11) 0.71648(10) 0.02249(19) Uani 1 1 d . . .
H13 H 0.4191 0.8449 0.6715 0.027 Uiso 1 1 calc R . .
C14 C 0.29232(14) 0.50984(13) 0.34531(12) 0.0317(2) Uani 1 1 d . . .
H14A H 0.3524 0.4274 0.3912 0.038 Uiso 1 1 calc R . .
H14B H 0.3711 0.5485 0.2588 0.038 Uiso 1 1 calc R . .
C15 C 0.16087(15) 0.45065(14) 0.30223(13) 0.0349(2) Uani 1 1 d . . .
H15A H 0.2090 0.3608 0.2411 0.052 Uiso 1 1 calc R . .
H15B H 0.1101 0.5300 0.2479 0.052 Uiso 1 1 calc R . .
H15C H 0.0777 0.4226 0.3896 0.052 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
N1 0.0241(4) 0.0212(4) 0.0222(4) -0.0016(3) -0.0078(3) -0.0045(3)
O1 0.0272(4) 0.0391(4) 0.0331(4) -0.0067(3) -0.0047(3) -0.0075(3)
O2 0.0951(9) 0.0443(5) 0.0285(4) 0.0017(4) -0.0250(5) -0.0073(5)
O3 0.0272(4) 0.0337(4) 0.0312(4) -0.0128(3) -0.0072(3) -0.0044(3)
C1 0.0286(5) 0.0281(5) 0.0223(4) -0.0016(3) -0.0072(4) -0.0074(4)
C2 0.0264(5) 0.0269(5) 0.0241(4) -0.0034(3) -0.0085(4) -0.0057(4)
C3 0.0425(6) 0.0317(5) 0.0290(5) 0.0000(4) -0.0183(4) -0.0058(4)
C4 0.0502(7) 0.0272(5) 0.0336(5) 0.0002(4) -0.0225(5) -0.0008(5)
C5 0.0294(5) 0.0225(4) 0.0263(5) 0.0001(3) -0.0093(4) -0.0056(4)
C6 0.0377(6) 0.0224(5) 0.0352(5) -0.0021(4) -0.0128(4) -0.0041(4)
C7 0.0485(7) 0.0266(5) 0.0419(6) -0.0073(4) -0.0198(5) -0.0067(5)
C8 0.0414(6) 0.0295(5) 0.0293(5) -0.0080(4) -0.0141(4) -0.0018(4)
C9 0.0257(5) 0.0256(5) 0.0240(4) -0.0028(3) -0.0095(4) -0.0039(4)
C10 0.0383(6) 0.0300(5) 0.0235(5) -0.0003(4) -0.0106(4) -0.0042(4)
C11 0.0451(6) 0.0257(5) 0.0287(5) 0.0014(4) -0.0146(5) -0.0028(4)
C12 0.0363(5) 0.0226(4) 0.0266(5) 0.0001(4) -0.0088(4) -0.0069(4)
C13 0.0236(4) 0.0226(4) 0.0218(4) -0.0018(3) -0.0065(3) -0.0049(3)
C14 0.0318(5) 0.0322(5) 0.0307(5) -0.0116(4) -0.0086(4) -0.0011(4)
C15 0.0381(6) 0.0350(6) 0.0345(5) -0.0108(4) -0.0142(5) -0.0035(4)

_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
N1 C5 1.4794(12) . ?
N1 C13 1.4803(12) . ?
N1 C9 1.4881(12) . ?
O1 C1 1.2039(13) . ?
O2 C3 1.2084(14) . ?
O3 C1 1.3391(12) . ?
O3 C14 1.4581(12) . ?
C1 C2 1.5189(13) . ?
C2 C3 1.5200(15) . ?
C2 C13 1.5453(13) . ?
C2 H2 1.0000 . ?
C3 C4 1.4933(15) . ?
C4 C5 1.5303(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5266(14) . ?
C5 H5 1.0000 . ?
C6 C7 1.5144(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.5180(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5244(14) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5229(14) . ?
C9 H9 1.0000 . ?
C10 C11 1.5219(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5211(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5297(13) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13 1.0000 . ?
C14 C15 1.5019(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C5 N1 C13 109.77(7) . . ?
C5 N1 C9 109.92(7) . . ?
C13 N1 C9 109.36(7) . . ?
C1 O3 C14 115.00(8) . . ?
O1 C1 O3 124.01(9) . . ?
O1 C1 C2 124.39(9) . . ?
O3 C1 C2 111.58(8) . . ?
C1 C2 C3 108.48(8) . . ?
C1 C2 C13 110.82(8) . . ?
C3 C2 C13 112.75(8) . . ?
C1 C2 H2 108.2 . . ?
C3 C2 H2 108.2 . . ?
C13 C2 H2 108.2 . . ?
O2 C3 C4 124.18(11) . . ?
O2 C3 C2 122.50(10) . . ?
C4 C3 C2 113.32(9) . . ?
C3 C4 C5 111.36(9) . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
N1 C5 C6 112.43(8) . . ?
N1 C5 C4 109.84(8) . . ?
C6 C5 C4 107.95(9) . . ?
N1 C5 H5 108.9 . . ?
C6 C5 H5 108.9 . . ?
C4 C5 H5 108.9 . . ?
C7 C6 C5 112.19(9) . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 C8 108.58(9) . . ?
C6 C7 H7A 110.0 . . ?
C8 C7 H7A 110.0 . . ?
C6 C7 H7B 110.0 . . ?
C8 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
C7 C8 C9 111.41(9) . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N1 C9 C10 110.95(8) . . ?
N1 C9 C8 111.03(8) . . ?
C10 C9 C8 109.58(8) . . ?
N1 C9 H9 108.4 . . ?
C10 C9 H9 108.4 . . ?
C8 C9 H9 108.4 . . ?
C11 C10 C9 111.38(8) . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C10 108.92(9) . . ?
C12 C11 H11A 109.9 . . ?
C10 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
C10 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C11 C12 C13 111.58(8) . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
N1 C13 C12 111.07(8) . . ?
N1 C13 C2 111.41(8) . . ?
C12 C13 C2 108.56(8) . . ?
N1 C13 H13 108.6 . . ?
C12 C13 H13 108.6 . . ?
C2 C13 H13 108.6 . . ?
O3 C14 C15 107.24(9) . . ?
O3 C14 H14A 110.3 . . ?
C15 C14 H14A 110.3 . . ?
O3 C14 H14B 110.3 . . ?
C15 C14 H14B 110.3 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 O3 C1 O1 0.03(15) . . . . ?
C14 O3 C1 C2 178.69(8) . . . . ?
O1 C1 C2 C3 83.40(13) . . . . ?
O3 C1 C2 C3 -95.25(10) . . . . ?
O1 C1 C2 C13 -40.88(13) . . . . ?
O3 C1 C2 C13 140.46(9) . . . . ?
C1 C2 C3 O2 11.72(16) . . . . ?
C13 C2 C3 O2 134.84(12) . . . . ?
C1 C2 C3 C4 -168.05(9) . . . . ?
C13 C2 C3 C4 -44.92(13) . . . . ?
O2 C3 C4 C5 -130.39(13) . . . . ?
C2 C3 C4 C5 49.38(13) . . . . ?
C13 N1 C5 C6 -176.11(8) . . . . ?
C9 N1 C5 C6 -55.79(11) . . . . ?
C13 N1 C5 C4 63.67(10) . . . . ?
C9 N1 C5 C4 -176.01(8) . . . . ?
C3 C4 C5 N1 -58.75(12) . . . . ?
C3 C4 C5 C6 178.35(9) . . . . ?
N1 C5 C6 C7 55.18(12) . . . . ?
C4 C5 C6 C7 176.48(10) . . . . ?
C5 C6 C7 C8 -53.69(13) . . . . ?
C6 C7 C8 C9 55.88(13) . . . . ?
C5 N1 C9 C10 179.76(8) . . . . ?
C13 N1 C9 C10 -59.66(10) . . . . ?
C5 N1 C9 C8 57.65(10) . . . . ?
C13 N1 C9 C8 178.22(8) . . . . ?
C7 C8 C9 N1 -59.14(12) . . . . ?
C7 C8 C9 C10 177.95(9) . . . . ?
N1 C9 C10 C11 58.41(12) . . . . ?
C8 C9 C10 C11 -178.63(9) . . . . ?
C9 C10 C11 C12 -54.53(12) . . . . ?
C10 C11 C12 C13 54.06(12) . . . . ?
C5 N1 C13 C12 179.79(8) . . . . ?
C9 N1 C13 C12 59.13(10) . . . . ?
C5 N1 C13 C2 -59.05(10) . . . . ?
C9 N1 C13 C2 -179.71(8) . . . . ?
C11 C12 C13 N1 -57.62(11) . . . . ?
C11 C12 C13 C2 179.56(8) . . . . ?
C1 C2 C13 N1 171.25(8) . . . . ?
C3 C2 C13 N1 49.44(11) . . . . ?
C1 C2 C13 C12 -66.13(10) . . . . ?
C3 C2 C13 C12 172.06(9) . . . . ?
C1 O3 C14 C15 -175.68(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        30.04
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.036