# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2002 

data_ohj46m 
_database_code_CSD                  184035

_journal_coden_Cambridge      182

loop_
_publ_author_name
'Andrew S. Edwards'
'Robert A.J. Wybrow'
'Craig Johnstone' 
'Harry Adams'
'Joseph P.A. Harrity'

_publ_contact_author_name     	'Dr J Harrity'  
_publ_contact_author_address 
;
Department of Chemistry
University of Sheffield
SHEFFIELD
S3 7HF
;

_publ_contact_author_email       'J.HARRITY@SHEFFIELD.AC.UK'

_publ_requested_journal       'Chemical Communications'

_publ_section_title		
;
A New Approach to Functionalised Spiropiperidines Through Tandem RCM
and Nitrogen-Directed Reactions
;

_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
'C17 H20 N2 O4' 
_chemical_formula_weight          316.35 

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)/c 

loop_ 
_symmetry_equiv_pos_as_xyz 
'x, y, z' 
'-x, y+1/2, -z+1/2' 
'-x, -y, -z' 
'x, -y-1/2, z-1/2' 

_cell_length_a                    11.882(3) 
_cell_length_b                    9.5188(19) 
_cell_length_c                    13.700(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  97.160(4) 
_cell_angle_gamma                 90.00 
_cell_volume                      1537.4(6) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     2011 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 

_exptl_crystal_description        BLOCK 
_exptl_crystal_colour             COLOURLESS 
_exptl_crystal_size_max           0.32 
_exptl_crystal_size_mid           0.29 
_exptl_crystal_size_min           0.18 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.367 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              672 
_exptl_absorpt_coefficient_mu     0.098 
_exptl_absorpt_correction_type    Empirical 
_exptl_absorpt_correction_T_min   0.9693 
_exptl_absorpt_correction_T_max   0.9826 
_exptl_absorpt_process_details    SADABS 

_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   'CCD area detector' 
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             6647 
_diffrn_reflns_av_R_equivalents   0.0765 
_diffrn_reflns_av_sigmaI/netI     0.0553 
_diffrn_reflns_limit_h_min        -13 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -8 
_diffrn_reflns_limit_k_max        10 
_diffrn_reflns_limit_l_min        -14 
_diffrn_reflns_limit_l_max        15 
_diffrn_reflns_theta_min          1.73 
_diffrn_reflns_theta_max          23.33 
_reflns_number_total              2224 
_reflns_number_gt                 1562 
_reflns_threshold_expression      >2sigma(I) 

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

_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^)+(0.1311P)^2^+1.4352P] 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      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          2224 
_refine_ls_number_parameters      208 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0992 
_refine_ls_R_factor_gt            0.0737 
_refine_ls_wR_factor_ref          0.2270 
_refine_ls_wR_factor_gt           0.2047 
_refine_ls_goodness_of_fit_ref    1.037 
_refine_ls_restrained_S_all       1.037 
_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 0.3810(2) 0.0734(3) 0.5424(2) 0.0377(8) Uani 1 1 d . . . 
O2 O 0.8692(3) 0.2291(4) 0.8486(3) 0.0586(10) Uani 1 1 d . . . 
O3 O 0.7592(3) 0.2776(3) 0.9584(2) 0.0480(9) Uani 1 1 d . . . 
O4 O 0.1930(2) 0.0523(4) 0.6442(2) 0.0519(9) Uani 1 1 d . . . 
N1 N 0.3070(3) 0.2884(3) 0.5743(3) 0.0354(9) Uani 1 1 d . . . 
N2 N 0.7754(3) 0.2518(4) 0.8742(3) 0.0396(9) Uani 1 1 d . . . 
C1 C 0.3886(3) 0.1864(4) 0.5852(3) 0.0288(9) Uani 1 1 d . . . 
C2 C 0.4904(3) 0.2133(4) 0.6598(3) 0.0278(9) Uani 1 1 d . . . 
C3 C 0.4827(3) 0.2857(4) 0.7463(3) 0.0336(10) Uani 1 1 d . . . 
H3A H 0.4122 0.3261 0.7574 0.040 Uiso 1 1 calc R . . 
C4 C 0.5760(3) 0.3004(4) 0.8172(3) 0.0337(10) Uani 1 1 d . . . 
H4A H 0.5705 0.3488 0.8770 0.040 Uiso 1 1 calc R . . 
C5 C 0.6767(3) 0.2422(4) 0.7977(3) 0.0320(10) Uani 1 1 d . . . 
C6 C 0.6879(3) 0.1706(4) 0.7118(3) 0.0334(10) Uani 1 1 d . . . 
H6A H 0.7592 0.1330 0.7004 0.040 Uiso 1 1 calc R . . 
C7 C 0.5936(3) 0.1543(4) 0.6427(3) 0.0312(9) Uani 1 1 d . . . 
H7A H 0.5991 0.1033 0.5839 0.037 Uiso 1 1 calc R . . 
C8 C 0.1932(3) 0.2554(5) 0.5204(3) 0.0421(12) Uani 1 1 d . . . 
C9 C 0.1996(4) 0.2700(6) 0.4116(3) 0.0573(14) Uani 1 1 d . . . 
H9A H 0.1241 0.2510 0.3747 0.069 Uiso 1 1 calc R . . 
H9B H 0.2537 0.2002 0.3910 0.069 Uiso 1 1 calc R . . 
C10 C 0.2381(5) 0.4182(7) 0.3876(4) 0.0769(18) Uani 1 1 d . . . 
H10A H 0.1785 0.4865 0.3997 0.092 Uiso 1 1 calc R . . 
H10B H 0.2482 0.4232 0.3171 0.092 Uiso 1 1 calc R . . 
C11 C 0.3508(4) 0.4589(6) 0.4505(3) 0.0567(14) Uani 1 1 d . . . 
H11A H 0.4137 0.4037 0.4287 0.068 Uiso 1 1 calc R . . 
H11B H 0.3666 0.5597 0.4405 0.068 Uiso 1 1 calc R . . 
C12 C 0.3456(4) 0.4322(4) 0.5581(3) 0.0417(11) Uani 1 1 d . . . 
H12A H 0.4217 0.4465 0.5952 0.050 Uiso 1 1 calc R . . 
H12B H 0.2929 0.5001 0.5831 0.050 Uiso 1 1 calc R . . 
C13 C 0.1044(4) 0.3541(6) 0.5562(3) 0.0527(13) Uani 1 1 d . . . 
H13A H 0.1349 0.4510 0.5585 0.063 Uiso 1 1 calc R . . 
H13B H 0.0357 0.3529 0.5072 0.063 Uiso 1 1 calc R . . 
C14 C 0.0702(4) 0.3195(6) 0.6545(3) 0.0551(13) Uani 1 1 d . . . 
H14A H 0.0168 0.3917 0.6729 0.066 Uiso 1 1 calc R . . 
H14B H 0.1380 0.3204 0.7044 0.066 Uiso 1 1 calc R . . 
C15 C 0.0141(4) 0.1757(6) 0.6533(4) 0.0529(13) Uani 1 1 d . . . 
H15A H 0.0065 0.1472 0.7217 0.063 Uiso 1 1 calc R . . 
H15B H -0.0631 0.1821 0.6169 0.063 Uiso 1 1 calc R . . 
C16 C 0.0781(4) 0.0693(5) 0.6078(3) 0.0523(13) Uani 1 1 d . . . 
H16A H 0.0361 -0.0206 0.5922 0.063 Uiso 1 1 calc R . . 
C17 C 0.1614(4) 0.1008(5) 0.5443(3) 0.0496(12) Uani 1 1 d . . . 
H17A H 0.1692 0.0303 0.4914 0.060 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 0.0365(15) 0.0386(18) 0.0366(17) -0.0083(14) -0.0006(12) 0.0043(13) 
O2 0.0355(18) 0.070(2) 0.067(2) -0.0141(18) -0.0060(15) 0.0086(15) 
O3 0.0558(18) 0.051(2) 0.0339(19) 0.0012(15) -0.0075(14) -0.0081(15) 
O4 0.0443(17) 0.063(2) 0.0458(19) 0.0036(15) -0.0035(13) -0.0056(15) 
N1 0.0296(17) 0.030(2) 0.045(2) -0.0070(16) -0.0009(14) 0.0025(15) 
N2 0.040(2) 0.033(2) 0.043(3) 0.0002(17) -0.0048(17) -0.0024(16) 
C1 0.0287(19) 0.033(2) 0.026(2) -0.0050(18) 0.0059(15) -0.0001(17) 
C2 0.0315(19) 0.026(2) 0.027(2) 0.0022(17) 0.0072(15) -0.0002(16) 
C3 0.0276(19) 0.037(2) 0.037(2) -0.0010(19) 0.0070(16) 0.0019(17) 
C4 0.038(2) 0.034(2) 0.030(2) -0.0028(18) 0.0060(17) -0.0014(18) 
C5 0.031(2) 0.030(2) 0.033(2) 0.0051(18) 0.0011(16) -0.0028(17) 
C6 0.0272(19) 0.036(2) 0.037(2) 0.0021(19) 0.0070(16) 0.0037(17) 
C7 0.034(2) 0.030(2) 0.031(2) -0.0012(17) 0.0087(16) 0.0002(17) 
C8 0.032(2) 0.061(3) 0.032(2) -0.009(2) -0.0028(17) 0.005(2) 
C9 0.050(3) 0.083(4) 0.038(3) 0.002(3) 0.001(2) -0.008(3) 
C10 0.077(4) 0.116(5) 0.034(3) 0.022(3) -0.008(2) 0.008(4) 
C11 0.054(3) 0.066(4) 0.049(3) 0.012(3) 0.004(2) 0.001(2) 
C12 0.044(2) 0.032(3) 0.046(3) 0.001(2) -0.0046(19) 0.0045(19) 
C13 0.041(2) 0.065(3) 0.051(3) 0.004(2) 0.002(2) 0.022(2) 
C14 0.056(3) 0.071(4) 0.040(3) -0.010(2) 0.012(2) 0.020(3) 
C15 0.035(2) 0.077(4) 0.045(3) 0.002(3) -0.0008(19) 0.000(2) 
C16 0.046(3) 0.064(3) 0.043(3) 0.000(2) -0.008(2) 0.001(2) 
C17 0.043(2) 0.054(3) 0.050(3) -0.019(2) 0.000(2) -0.008(2) 

_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 1.223(5) . ? 
O2 N2 1.228(5) . ? 
O3 N2 1.218(5) . ? 
O4 C16 1.403(5) . ? 
O4 C17 1.449(6) . ? 
N1 C1 1.367(5) . ? 
N1 C12 1.469(5) . ? 
N1 C8 1.491(5) . ? 
N2 C5 1.475(5) . ? 
C1 C2 1.505(5) . ? 
C2 C3 1.385(6) . ? 
C2 C7 1.395(5) . ? 
C3 C4 1.387(5) . ? 
C4 C5 1.375(6) . ? 
C5 C6 1.381(6) . ? 
C6 C7 1.382(5) . ? 
C8 C9 1.508(6) . ? 
C8 C13 1.538(6) . ? 
C8 C17 1.563(7) . ? 
C9 C10 1.532(8) . ? 
C10 C11 1.549(7) . ? 
C11 C12 1.505(6) . ? 
C13 C14 1.490(7) . ? 
C14 C15 1.522(7) . ? 
C15 C16 1.453(7) . ? 
C16 C17 1.429(7) . ? 

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 
C16 O4 C17 60.1(3) . . ? 
C1 N1 C12 116.6(3) . . ? 
C1 N1 C8 119.4(3) . . ? 
C12 N1 C8 113.8(3) . . ? 
O3 N2 O2 124.2(3) . . ? 
O3 N2 C5 118.7(4) . . ? 
O2 N2 C5 117.1(4) . . ? 
O1 C1 N1 124.3(3) . . ? 
O1 C1 C2 118.7(3) . . ? 
N1 C1 C2 116.9(3) . . ? 
C3 C2 C7 119.9(3) . . ? 
C3 C2 C1 122.2(3) . . ? 
C7 C2 C1 117.8(3) . . ? 
C2 C3 C4 121.1(4) . . ? 
C5 C4 C3 117.6(4) . . ? 
C4 C5 C6 122.9(3) . . ? 
C4 C5 N2 118.1(4) . . ? 
C6 C5 N2 119.0(3) . . ? 
C5 C6 C7 118.9(3) . . ? 
C6 C7 C2 119.6(4) . . ? 
N1 C8 C9 108.4(3) . . ? 
N1 C8 C13 109.2(3) . . ? 
C9 C8 C13 112.3(4) . . ? 
N1 C8 C17 108.9(3) . . ? 
C9 C8 C17 109.7(4) . . ? 
C13 C8 C17 108.4(4) . . ? 
C8 C9 C10 110.5(4) . . ? 
C9 C10 C11 111.8(4) . . ? 
C12 C11 C10 111.4(4) . . ? 
N1 C12 C11 110.9(4) . . ? 
C14 C13 C8 115.3(4) . . ? 
C13 C14 C15 111.0(4) . . ? 
C16 C15 C14 112.3(4) . . ? 
O4 C16 C17 61.6(3) . . ? 
O4 C16 C15 117.8(4) . . ? 
C17 C16 C15 123.6(5) . . ? 
C16 C17 O4 58.3(3) . . ? 
C16 C17 C8 121.9(4) . . ? 
O4 C17 C8 117.2(3) . . ? 

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 
C12 N1 C1 O1 -132.6(4) . . . . ? 
C8 N1 C1 O1 10.5(6) . . . . ? 
C12 N1 C1 C2 51.3(5) . . . . ? 
C8 N1 C1 C2 -165.6(3) . . . . ? 
O1 C1 C2 C3 -141.9(4) . . . . ? 
N1 C1 C2 C3 34.4(5) . . . . ? 
O1 C1 C2 C7 33.8(5) . . . . ? 
N1 C1 C2 C7 -149.9(4) . . . . ? 
C7 C2 C3 C4 -0.4(6) . . . . ? 
C1 C2 C3 C4 175.2(4) . . . . ? 
C2 C3 C4 C5 1.0(6) . . . . ? 
C3 C4 C5 C6 -0.3(6) . . . . ? 
C3 C4 C5 N2 -177.4(3) . . . . ? 
O3 N2 C5 C4 18.0(5) . . . . ? 
O2 N2 C5 C4 -163.9(4) . . . . ? 
O3 N2 C5 C6 -159.2(4) . . . . ? 
O2 N2 C5 C6 18.9(5) . . . . ? 
C4 C5 C6 C7 -1.0(6) . . . . ? 
N2 C5 C6 C7 176.1(3) . . . . ? 
C5 C6 C7 C2 1.6(6) . . . . ? 
C3 C2 C7 C6 -1.0(6) . . . . ? 
C1 C2 C7 C6 -176.7(3) . . . . ? 
C1 N1 C8 C9 -82.8(5) . . . . ? 
C12 N1 C8 C9 61.3(5) . . . . ? 
C1 N1 C8 C13 154.6(4) . . . . ? 
C12 N1 C8 C13 -61.4(5) . . . . ? 
C1 N1 C8 C17 36.4(5) . . . . ? 
C12 N1 C8 C17 -179.5(3) . . . . ? 
N1 C8 C9 C10 -57.6(5) . . . . ? 
C13 C8 C9 C10 63.1(5) . . . . ? 
C17 C8 C9 C10 -176.4(4) . . . . ? 
C8 C9 C10 C11 54.0(6) . . . . ? 
C9 C10 C11 C12 -50.3(6) . . . . ? 
C1 N1 C12 C11 86.7(4) . . . . ? 
C8 N1 C12 C11 -58.4(5) . . . . ? 
C10 C11 C12 N1 51.3(5) . . . . ? 
N1 C8 C13 C14 -75.8(5) . . . . ? 
C9 C8 C13 C14 163.9(4) . . . . ? 
C17 C8 C13 C14 42.6(5) . . . . ? 
C8 C13 C14 C15 -62.6(5) . . . . ? 
C13 C14 C15 C16 47.4(5) . . . . ? 
C17 O4 C16 C15 -115.2(5) . . . . ? 
C14 C15 C16 O4 53.8(6) . . . . ? 
C14 C15 C16 C17 -18.9(6) . . . . ? 
C15 C16 C17 O4 106.1(5) . . . . ? 
O4 C16 C17 C8 -104.3(4) . . . . ? 
C15 C16 C17 C8 1.7(6) . . . . ? 
C16 O4 C17 C8 112.5(5) . . . . ? 
N1 C8 C17 C16 106.3(4) . . . . ? 
C9 C8 C17 C16 -135.2(4) . . . . ? 
C13 C8 C17 C16 -12.3(5) . . . . ? 
N1 C8 C17 O4 38.4(5) . . . . ? 
C9 C8 C17 O4 156.8(4) . . . . ? 
C13 C8 C17 O4 -80.3(4) . . . . ? 

_diffrn_measured_fraction_theta_max    0.998 
_diffrn_reflns_theta_full              23.33 
_diffrn_measured_fraction_theta_full   0.998 
_refine_diff_density_max    1.264 
_refine_diff_density_min   -0.385 
_refine_diff_density_rms    0.073