# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2000
# CCDC Number: 207/450

data_compound #18

# SUPPLEMENTARY CRYSTALLOGRAPHIC DATA OF THE MANUSCRIPT:

# Regio-and Diastereo-Selectivity in 1,3-Dipolar Cycloadditions of
# Nitrile Oxides to 4-Substituted 2-Cyclopentenones

_audit_creation_date            'May 18, 2000'
_audit_creation_method          'SHELXL-97' 

# SUBMISSION DETAILS

_publ_contact_author_name    'Prof. Alessandro Sega'
_publ_contact_author_address
; Istituto di Chimica Organica,
  Universit\`a degli Studi di Siena
  Via Aldo Moro
  I-53100 Siena
  Italy
;
_publ_contact_author_email          'sega@unisi.it'
_publ_contact_author_fax            '+39 0577 234277'
_publ_contact_author_phone          '+39 0577 234278'
_publ_contact_letter
;
;
_publ_requested_journal             
'Journal of the Chemical Society, Perkin Transactions 1'

#-------------------------- data section of block ---------------------------

_chemical_name_systematic  
;
(3aSR, 4SR, 6aSR, 6RS)-3-(2,6-dichlorophenyl)-6-methyl-4-
methylcarbonyloxy-5, 6-dihydro-4H cyclopenta [d][1,2] oxazol-6-yl acetate  
; 
_chemical_formula_moiety          'C17 H17 C12 N O5' 
_chemical_formula_sum 
 'C17 H17 Cl2 N O5' 
_chemical_formula_weight          386.22 
 
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' 
 'Cl'  'Cl'   0.1484   0.1585 
 '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                    17.410(3) 
_cell_length_b                    8.7394(15) 
_cell_length_c                    12.1881(15) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  107.290(10) 
_cell_angle_gamma                 90.00 
_cell_volume                      1770.7(5) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     32
_cell_measurement_theta_min        9.318
_cell_measurement_theta_max       36.902
 
_exptl_crystal_description        'prism'
_exptl_crystal_colour             'colourless' 
_exptl_crystal_size_max           0.2 
_exptl_crystal_size_mid           0.1 
_exptl_crystal_size_min           0.08 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.449 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              800 
_exptl_absorpt_coefficient_mu     0.394 
_exptl_absorpt_correction_type    'none' 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(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       'Siemens P4'
_diffrn_measurement_method       '\w scans'
_diffrn_standards_number          3
_diffrn_standards_interval_count  97
_diffrn_standards_decay_%         5.95
_computing_data_collection       'Siemens XSCANS'
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_reduction        'Siemens XSCANS'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
 

_diffrn_measurement_device_type  'Siemens P4'
_diffrn_reflns_number             4101 
_diffrn_reflns_av_R_equivalents   0.0243 
_diffrn_reflns_av_sigmaI/netI     0.0564 
_diffrn_reflns_limit_h_min        -20 
_diffrn_reflns_limit_h_max        20 
_diffrn_reflns_limit_k_min        -10 
_diffrn_reflns_limit_k_max        1 
_diffrn_reflns_limit_l_min        -1 
_diffrn_reflns_limit_l_max        14 
_diffrn_reflns_theta_min          1.22 
_diffrn_reflns_theta_max          25.00 
_reflns_number_total              3126 
_reflns_number_gt                 1974 
_reflns_threshold_expression      >2sigma(I) 
 
_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^)+(0.0356P)^2^+0.5238P] 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          3126 
_refine_ls_number_parameters      230 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0925 
_refine_ls_R_factor_gt            0.0487 
_refine_ls_wR_factor_ref          0.1090 
_refine_ls_wR_factor_gt           0.0927 
_refine_ls_goodness_of_fit_ref    1.019 
_refine_ls_restrained_S_all       1.019 
_refine_ls_shift/su_max           0.004 
_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 
Cl1 Cl 0.92834(5) 0.22049(12) 0.47232(9) 0.0618(3) Uani 1 1 d . . . 
Cl2 Cl 0.76779(6) 0.51025(12) 0.73184(8) 0.0647(3) Uani 1 1 d . . . 
N2 N 0.74354(15) 0.2006(3) 0.5912(2) 0.0506(7) Uani 1 1 d . . . 
O1 O 0.67249(12) 0.1436(3) 0.5134(2) 0.0548(7) Uani 1 1 d . . . 
O2 O 0.72792(12) 0.5987(2) 0.46185(19) 0.0446(6) Uani 1 1 d . . . 
O3 O 0.81960(14) 0.6250(3) 0.3685(3) 0.0734(8) Uani 1 1 d . . . 
O4 O 0.52572(11) 0.2118(3) 0.38975(19) 0.0458(6) Uani 1 1 d . . . 
O5 O 0.43065(15) 0.3880(4) 0.3139(3) 0.0959(11) Uani 1 1 d . . . 
C3 C 0.77732(17) 0.2933(4) 0.5392(3) 0.0383(7) Uani 1 1 d . . . 
C3A C 0.73269(16) 0.3181(3) 0.4138(3) 0.0364(7) Uani 1 1 d . . . 
H3A H 0.7659 0.2966 0.3654 0.050(3) Uiso 1 1 d R . . 
C4 C 0.69048(16) 0.4752(3) 0.3863(3) 0.0384(7) Uani 1 1 d . . . 
H4 H 0.6853 0.5029 0.3082 0.050(3) Uiso 1 1 d R . . 
C5 C 0.60713(17) 0.4493(4) 0.3990(3) 0.0453(8) Uani 1 1 d . . . 
H5A H 0.5694 0.5244 0.3573 0.050(3) Uiso 1 1 d R . . 
H5B H 0.6090 0.4521 0.4785 0.050(3) Uiso 1 1 d R . . 
C6 C 0.58585(17) 0.2898(4) 0.3483(3) 0.0409(8) Uani 1 1 d . . . 
C6A C 0.66490(17) 0.2003(4) 0.3991(3) 0.0414(8) Uani 1 1 d . . . 
H6A H 0.6696 0.1187 0.3487 0.050(3) Uiso 1 1 d R . . 
C7 C 0.79135(19) 0.6676(4) 0.4411(3) 0.0513(9) Uani 1 1 d . . . 
C8 C 0.8198(2) 0.8002(4) 0.5202(3) 0.0682(11) Uani 1 1 d . . . 
H8A H 0.8228 0.7707 0.5973 0.080 Uiso 1 1 calc R . . 
H8B H 0.7828 0.8839 0.4967 0.080 Uiso 1 1 calc R . . 
H8C H 0.8721 0.8313 0.5175 0.080 Uiso 1 1 calc R . . 
C9 C 0.5628(2) 0.2846(5) 0.2178(3) 0.0612(10) Uani 1 1 d . . . 
H9A H 0.6084 0.3125 0.1932 0.080 Uiso 1 1 calc R . . 
H9B H 0.5196 0.3551 0.1861 0.080 Uiso 1 1 calc R . . 
H9C H 0.5458 0.1830 0.1917 0.080 Uiso 1 1 calc R . . 
C10 C 0.45172(19) 0.2729(5) 0.3678(3) 0.0551(10) Uani 1 1 d . . . 
C11 C 0.40036(19) 0.1789(4) 0.4205(3) 0.0588(10) Uani 1 1 d . . . 
H11A H 0.4035 0.2189 0.4950 0.080 Uiso 1 1 calc R . . 
H11B H 0.4189 0.0749 0.4279 0.080 Uiso 1 1 calc R . . 
H11C H 0.3456 0.1824 0.3724 0.080 Uiso 1 1 calc R . . 
C1' C 0.85308(17) 0.3705(4) 0.6064(3) 0.0388(7) Uani 1 1 d . . . 
C2' C 0.92496(18) 0.3479(4) 0.5804(3) 0.0453(8) Uani 1 1 d . . . 
C3' C 0.99572(19) 0.4207(4) 0.6408(3) 0.0567(10) Uani 1 1 d . . . 
H3'A H 1.0444 0.4036 0.6210 0.050(3) Uiso 1 1 d R . . 
C4' C 0.9945(2) 0.5170(5) 0.7300(3) 0.0638(11) Uani 1 1 d . . . 
H4'A H 1.0432 0.5675 0.7728 0.050(3) Uiso 1 1 d R . . 
C5' C 0.9251(2) 0.5418(5) 0.7584(3) 0.0608(10) Uani 1 1 d . . . 
H5'A H 0.9251 0.6088 0.8209 0.050(3) Uiso 1 1 d R . . 
C6' C 0.85542(19) 0.4698(4) 0.6969(3) 0.0442(8) 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 
Cl1 0.0447(5) 0.0671(6) 0.0768(7) -0.0117(6) 0.0228(5) 0.0073(5) 
Cl2 0.0718(6) 0.0712(7) 0.0657(6) -0.0076(6) 0.0427(5) -0.0065(5) 
N2 0.0428(15) 0.0481(18) 0.0605(19) 0.0143(16) 0.0148(14) -0.0007(14) 
O1 0.0411(12) 0.0519(15) 0.0708(17) 0.0172(14) 0.0156(12) -0.0087(12) 
O2 0.0421(12) 0.0370(13) 0.0577(15) -0.0008(12) 0.0194(11) -0.0084(10) 
O3 0.0577(16) 0.0704(19) 0.109(2) -0.0110(18) 0.0497(17) -0.0179(14) 
O4 0.0337(11) 0.0445(13) 0.0641(15) 0.0019(12) 0.0218(11) -0.0048(10) 
O5 0.0490(16) 0.076(2) 0.168(3) 0.046(2) 0.0418(19) 0.0165(15) 
C3 0.0350(15) 0.0341(17) 0.049(2) 0.0018(17) 0.0169(15) 0.0013(15) 
C3A 0.0299(15) 0.0408(19) 0.0425(18) -0.0031(16) 0.0168(14) -0.0030(14) 
C4 0.0346(15) 0.0357(18) 0.0453(19) 0.0015(16) 0.0123(14) -0.0041(14) 
C5 0.0355(16) 0.0368(19) 0.065(2) 0.0024(18) 0.0172(16) 0.0011(15) 
C6 0.0323(15) 0.0438(19) 0.050(2) -0.0001(18) 0.0182(15) -0.0068(15) 
C6A 0.0352(16) 0.0388(19) 0.055(2) -0.0068(18) 0.0203(15) -0.0034(15) 
C7 0.0395(18) 0.043(2) 0.073(3) 0.013(2) 0.0186(19) -0.0001(16) 
C8 0.072(3) 0.051(2) 0.078(3) -0.001(2) 0.017(2) -0.023(2) 
C9 0.055(2) 0.074(3) 0.053(2) 0.000(2) 0.0137(18) -0.017(2) 
C10 0.0304(17) 0.055(2) 0.082(3) -0.004(2) 0.0195(18) -0.0051(17) 
C11 0.0442(19) 0.064(3) 0.076(3) -0.012(2) 0.0307(19) -0.0117(18) 
C1' 0.0370(16) 0.0355(18) 0.0439(19) 0.0087(16) 0.0122(15) -0.0003(14) 
C2' 0.0409(17) 0.044(2) 0.049(2) 0.0075(18) 0.0108(16) 0.0021(16) 
C3' 0.0396(19) 0.060(2) 0.071(3) 0.007(2) 0.0163(19) -0.0010(18) 
C4' 0.052(2) 0.065(3) 0.065(3) 0.001(2) 0.005(2) -0.019(2) 
C5' 0.069(2) 0.065(3) 0.048(2) -0.005(2) 0.016(2) -0.015(2) 
C6' 0.0515(19) 0.044(2) 0.0394(19) 0.0053(17) 0.0171(16) -0.0042(16) 
 
_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 
Cl1 C2' 1.739(4) . ? 
Cl2 C6' 1.738(3) . ? 
N2 C3 1.275(4) . ? 
N2 O1 1.407(3) . ? 
O1 C6A 1.447(4) . ? 
O2 C7 1.346(4) . ? 
O2 C4 1.443(3) . ? 
O3 C7 1.193(4) . ? 
O4 C10 1.346(4) . ? 
O4 C6 1.459(3) . ? 
O5 C10 1.199(4) . ? 
C3 C1' 1.491(4) . ? 
C3 C3A 1.510(4) . ? 
C3A C6A 1.536(4) . ? 
C3A C4 1.546(4) . ? 
C4 C5 1.522(4) . ? 
C5 C6 1.525(4) . ? 
C6 C9 1.521(4) . ? 
C6 C6A 1.544(4) . ? 
C7 C8 1.495(5) . ? 
C10 C11 1.492(5) . ? 
C1' C2' 1.393(4) . ? 
C1' C6' 1.395(4) . ? 
C2' C3' 1.388(4) . ? 
C3' C4' 1.380(5) . ? 
C4' C5' 1.370(5) . ? 
C5' C6' 1.374(5) . ? 
 
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 
C3 N2 O1 109.5(3) . . ? 
N2 O1 C6A 109.7(2) . . ? 
C7 O2 C4 117.1(3) . . ? 
C10 O4 C6 119.3(3) . . ? 
N2 C3 C1' 118.6(3) . . ? 
N2 C3 C3A 114.8(3) . . ? 
C1' C3 C3A 126.6(3) . . ? 
C3 C3A C6A 99.7(2) . . ? 
C3 C3A C4 114.6(3) . . ? 
C6A C3A C4 105.7(2) . . ? 
O2 C4 C5 108.0(2) . . ? 
O2 C4 C3A 115.5(2) . . ? 
C5 C4 C3A 104.6(2) . . ? 
C4 C5 C6 102.6(2) . . ? 
O4 C6 C9 110.8(3) . . ? 
O4 C6 C5 113.6(3) . . ? 
C9 C6 C5 114.1(3) . . ? 
O4 C6 C6A 105.7(3) . . ? 
C9 C6 C6A 109.3(3) . . ? 
C5 C6 C6A 102.8(2) . . ? 
O1 C6A C3A 105.6(2) . . ? 
O1 C6A C6 112.0(2) . . ? 
C3A C6A C6 105.6(3) . . ? 
O3 C7 O2 122.8(4) . . ? 
O3 C7 C8 126.1(3) . . ? 
O2 C7 C8 111.1(3) . . ? 
O5 C10 O4 124.1(3) . . ? 
O5 C10 C11 125.0(3) . . ? 
O4 C10 C11 110.9(3) . . ? 
C2' C1' C6' 116.8(3) . . ? 
C2' C1' C3 121.2(3) . . ? 
C6' C1' C3 121.9(3) . . ? 
C3' C2' C1' 122.0(3) . . ? 
C3' C2' Cl1 118.1(3) . . ? 
C1' C2' Cl1 119.9(3) . . ? 
C4' C3' C2' 118.6(3) . . ? 
C5' C4' C3' 121.1(3) . . ? 
C4' C5' C6' 119.5(4) . . ? 
C5' C6' C1' 122.0(3) . . ? 
C5' C6' Cl2 118.1(3) . . ? 
C1' C6' Cl2 119.9(2) . . ? 
 
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 
C3 N2 O1 C6A 4.3(3) . . . . ? 
O1 N2 C3 C1' 178.6(3) . . . . ? 
O1 N2 C3 C3A 1.1(4) . . . . ? 
N2 C3 C3A C6A -5.6(4) . . . . ? 
C1' C3 C3A C6A 177.2(3) . . . . ? 
N2 C3 C3A C4 106.8(3) . . . . ? 
C1' C3 C3A C4 -70.4(4) . . . . ? 
C7 O2 C4 C5 -162.0(3) . . . . ? 
C7 O2 C4 C3A 81.4(3) . . . . ? 
C3 C3A C4 O2 29.2(3) . . . . ? 
C6A C3A C4 O2 137.9(3) . . . . ? 
C3 C3A C4 C5 -89.4(3) . . . . ? 
C6A C3A C4 C5 19.4(3) . . . . ? 
O2 C4 C5 C6 -162.3(2) . . . . ? 
C3A C4 C5 C6 -38.8(3) . . . . ? 
C10 O4 C6 C9 -67.8(4) . . . . ? 
C10 O4 C6 C5 62.1(4) . . . . ? 
C10 O4 C6 C6A 173.9(3) . . . . ? 
C4 C5 C6 O4 156.7(3) . . . . ? 
C4 C5 C6 C9 -75.1(3) . . . . ? 
C4 C5 C6 C6A 43.0(3) . . . . ? 
N2 O1 C6A C3A -7.6(3) . . . . ? 
N2 O1 C6A C6 -122.2(3) . . . . ? 
C3 C3A C6A O1 7.5(3) . . . . ? 
C4 C3A C6A O1 -111.6(3) . . . . ? 
C3 C3A C6A C6 126.3(3) . . . . ? 
C4 C3A C6A C6 7.2(3) . . . . ? 
O4 C6 C6A O1 -35.7(3) . . . . ? 
C9 C6 C6A O1 -155.0(3) . . . . ? 
C5 C6 C6A O1 83.5(3) . . . . ? 
O4 C6 C6A C3A -150.3(2) . . . . ? 
C9 C6 C6A C3A 90.5(3) . . . . ? 
C5 C6 C6A C3A -31.0(3) . . . . ? 
C4 O2 C7 O3 -4.4(5) . . . . ? 
C4 O2 C7 C8 175.7(3) . . . . ? 
C6 O4 C10 O5 1.3(6) . . . . ? 
C6 O4 C10 C11 -178.2(3) . . . . ? 
N2 C3 C1' C2' 118.1(4) . . . . ? 
C3A C3 C1' C2' -64.8(4) . . . . ? 
N2 C3 C1' C6' -62.8(4) . . . . ? 
C3A C3 C1' C6' 114.4(4) . . . . ? 
C6' C1' C2' C3' -0.3(5) . . . . ? 
C3 C1' C2' C3' 178.9(3) . . . . ? 
C6' C1' C2' Cl1 177.6(2) . . . . ? 
C3 C1' C2' Cl1 -3.2(4) . . . . ? 
C1' C2' C3' C4' 0.7(5) . . . . ? 
Cl1 C2' C3' C4' -177.2(3) . . . . ? 
C2' C3' C4' C5' -0.5(6) . . . . ? 
C3' C4' C5' C6' -0.1(6) . . . . ? 
C4' C5' C6' C1' 0.5(6) . . . . ? 
C4' C5' C6' Cl2 -177.5(3) . . . . ? 
C2' C1' C6' C5' -0.4(5) . . . . ? 
C3 C1' C6' C5' -179.6(3) . . . . ? 
C2' C1' C6' Cl2 177.6(2) . . . . ? 
C3 C1' C6' Cl2 -1.6(4) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.999 
_diffrn_reflns_theta_full              25.00 
_diffrn_measured_fraction_theta_full   0.999 
_refine_diff_density_max    0.218 
_refine_diff_density_min   -0.238 
_refine_diff_density_rms    0.045