Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2002
data_dreg2 

_database_code_CSD	174518


_journal_coden_Cambridge      182

_publ_requested_journal       'Chemical Communications'

loop_
_publ_author_name
'Stevenson, Paul James'
'Nieuwenhuyzen, Mark'
'Osborne, Daire'

_publ_contact_author_name     	'Dr Paul James Stevenson'  
_publ_contact_author_address 
;
Chemistry
Queens University
School of Chemistry
Queens University
Belfast
Northern Ireland
BT9 5AG
UNITED KINGDOM
;

_publ_contact_author_email       'P.STEVENSON@QUB.AC.UK'

_publ_section_title		
;
Three Componet Coupling Reactions of N-Acetyl-2-azetine
;

_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
'C25 H27 N3 O2' 
_chemical_formula_sum 
'C25 H27 N3 O2' 
_chemical_formula_weight          401.50 

loop_ 
_atom_type_symbol 
_atom_type_description 
_atom_type_scat_dispersion_real 
_atom_type_scat_dispersion_imag 
_atom_type_scat_source 
'C'  'C'   0.0181   0.0091 
'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'   0.0311   0.0180 
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
'O'  'O'   0.0492   0.0322 
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

_symmetry_cell_setting            Orthorhombic 
_symmetry_space_group_name_H-M    Pbca 

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' 
'-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                    17.607(2) 
_cell_length_b                    9.595(3) 
_cell_length_c                    25.870(8) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      4370(2) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     25 
_cell_measurement_theta_min       5 
_cell_measurement_theta_max       20 

_exptl_crystal_description        needle 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.52 
_exptl_crystal_size_mid           0.12 
_exptl_crystal_size_min           0.08 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.220 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1712 
_exptl_absorpt_coefficient_mu     0.621 
_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      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Siemens P4' 
_diffrn_measurement_method        'omega scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             2700 
_diffrn_reflns_av_R_equivalents   0.0000 
_diffrn_reflns_av_sigmaI/netI     0.0551 
_diffrn_reflns_limit_h_min        -18 
_diffrn_reflns_limit_h_max        0 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        10 
_diffrn_reflns_limit_l_min        -27 
_diffrn_reflns_limit_l_max        0 
_diffrn_reflns_theta_min          3.42 
_diffrn_reflns_theta_max          54.98 
_reflns_number_total              2700 
_reflns_number_gt                 1405 
_reflns_threshold_expression      >2sigma(I) 

_computing_data_collection        'XSCANS (Fait, 1993)' 
_computing_cell_refinement        'XSCANS (Fait, 1993)' 
_computing_data_reduction         'XSCANS (Fait, 1993)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXTL (Sheldrick, 1998)' 
_computing_molecular_graphics     'SHELXTL (Sheldrick, 1998)' 
_computing_publication_material   'SHELXTL (Sheldrick, 1998)' 

_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^)+(0.1312P)^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     calc 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          2700 
_refine_ls_number_parameters      273 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1210 
_refine_ls_R_factor_gt            0.0706 
_refine_ls_wR_factor_ref          0.2382 
_refine_ls_wR_factor_gt           0.1790 
_refine_ls_goodness_of_fit_ref    1.002 
_refine_ls_restrained_S_all       1.002 
_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 
C1 C 0.1070(3) -0.0288(5) 0.53336(18) 0.0603(13) Uani 1 1 d . . . 
H1 H 0.0517 -0.0177 0.5337 0.072 Uiso 1 1 calc R . . 
N2 N 0.1218(2) -0.1721(4) 0.51923(16) 0.0682(12) Uani 1 1 d . . . 
H2 H 0.1442 -0.1917 0.4906 0.082 Uiso 1 1 calc R . . 
C3 C 0.0994(3) -0.2774(5) 0.5526(2) 0.0574(13) Uani 1 1 d . . . 
C4 C 0.0937(3) -0.4134(6) 0.5355(2) 0.0713(15) Uani 1 1 d . . . 
H4 H 0.1047 -0.4344 0.5012 0.086 Uiso 1 1 calc R . . 
C5 C 0.0721(3) -0.5177(6) 0.5686(2) 0.0771(16) Uani 1 1 d . . . 
H5 H 0.0676 -0.6083 0.5562 0.093 Uiso 1 1 calc R . . 
C6 C 0.0569(3) -0.4911(6) 0.6197(2) 0.0772(16) Uani 1 1 d . . . 
H6 H 0.0431 -0.5625 0.6421 0.093 Uiso 1 1 calc R . . 
C7 C 0.0628(3) -0.3562(6) 0.6368(2) 0.0691(15) Uani 1 1 d . . . 
H7 H 0.0523 -0.3370 0.6713 0.083 Uiso 1 1 calc R . . 
C8 C 0.0837(3) -0.2476(5) 0.60451(18) 0.0558(13) Uani 1 1 d . . . 
C9 C 0.0874(3) -0.0997(5) 0.62489(19) 0.0578(13) Uani 1 1 d . . . 
H9 H 0.1121 -0.1015 0.6588 0.069 Uiso 1 1 calc R . . 
C10 C 0.1342(2) -0.0048(5) 0.58887(18) 0.0572(13) Uani 1 1 d . . . 
H10 H 0.1234 0.0922 0.5981 0.069 Uiso 1 1 calc R . . 
C11 C 0.2202(2) -0.0299(6) 0.59587(19) 0.0628(14) Uani 1 1 d . . . 
H11A H 0.2315 -0.1273 0.5893 0.075 Uiso 1 1 calc R . . 
H11B H 0.2480 0.0257 0.5709 0.075 Uiso 1 1 calc R . . 
N12 N 0.2449(2) 0.0061(4) 0.64750(15) 0.0592(11) Uani 1 1 d . . . 
H12 H 0.2435 0.0925 0.6563 0.071 Uiso 1 1 calc R . . 
C13 C 0.2697(3) -0.0852(6) 0.6822(2) 0.0646(14) Uani 1 1 d . . . 
O14 O 0.2712(3) -0.2106(4) 0.67434(17) 0.0984(15) Uani 1 1 d . . . 
C15 C 0.2968(3) -0.0254(6) 0.7325(2) 0.0822(17) Uani 1 1 d . . . 
H15A H 0.2755 -0.0777 0.7606 0.123 Uiso 1 1 calc R . . 
H15B H 0.2810 0.0701 0.7350 0.123 Uiso 1 1 calc R . . 
H15C H 0.3512 -0.0304 0.7340 0.123 Uiso 1 1 calc R . . 
C16 C 0.1370(3) 0.0699(5) 0.49226(19) 0.0589(13) Uani 1 1 d . . . 
C17 C 0.2061(3) 0.0483(6) 0.4669(2) 0.0753(16) Uani 1 1 d . . . 
H17 H 0.2372 -0.0254 0.4768 0.090 Uiso 1 1 calc R . . 
C18 C 0.2286(3) 0.1357(7) 0.4275(2) 0.0804(17) Uani 1 1 d . . . 
H18 H 0.2753 0.1218 0.4115 0.097 Uiso 1 1 calc R . . 
C19 C 0.1823(3) 0.2436(6) 0.4114(2) 0.0714(15) Uani 1 1 d . . . 
C20 C 0.1150(3) 0.2684(6) 0.4373(2) 0.0665(14) Uani 1 1 d . . . 
H20 H 0.0844 0.3431 0.4278 0.080 Uiso 1 1 calc R . . 
C21 C 0.0934(3) 0.1827(5) 0.47698(19) 0.0587(13) Uani 1 1 d . . . 
H21 H 0.0482 0.2008 0.4942 0.070 Uiso 1 1 calc R . . 
O22 O 0.2078(2) 0.3194(5) 0.36922(17) 0.1007(14) Uani 1 1 d . . . 
C23 C 0.1522(4) 0.3924(9) 0.3401(3) 0.126(3) Uani 1 1 d . . . 
H23A H 0.1757 0.4339 0.3103 0.189 Uiso 1 1 calc R . . 
H23B H 0.1300 0.4640 0.3611 0.189 Uiso 1 1 calc R . . 
H23C H 0.1134 0.3287 0.3291 0.189 Uiso 1 1 calc R . . 
N24 N 0.0093(2) -0.0488(4) 0.63169(16) 0.0653(12) Uani 1 1 d . . . 
H24 H -0.0263 -0.0941 0.6163 0.078 Uiso 1 1 calc R . . 
C25 C -0.0116(3) 0.0651(5) 0.66062(18) 0.0535(12) Uani 1 1 d . . . 
C26 C 0.0385(3) 0.1362(5) 0.69323(19) 0.0643(14) Uani 1 1 d . . . 
H26 H 0.0891 0.1092 0.6950 0.077 Uiso 1 1 calc R . . 
C27 C 0.0129(3) 0.2463(6) 0.72277(19) 0.0703(15) Uani 1 1 d . . . 
H27 H 0.0464 0.2907 0.7451 0.084 Uiso 1 1 calc R . . 
C28 C -0.0613(4) 0.2920(6) 0.7199(2) 0.0775(17) Uani 1 1 d . . . 
H28 H -0.0777 0.3668 0.7399 0.093 Uiso 1 1 calc R . . 
C29 C -0.1107(3) 0.2246(6) 0.6868(2) 0.0749(16) Uani 1 1 d . . . 
H29 H -0.1608 0.2543 0.6843 0.090 Uiso 1 1 calc R . . 
C30 C -0.0861(3) 0.1140(5) 0.6576(2) 0.0621(14) Uani 1 1 d . . . 
H30 H -0.1200 0.0706 0.6353 0.075 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 
C1 0.050(3) 0.063(3) 0.067(3) -0.005(3) 0.002(2) 0.002(3) 
N2 0.071(3) 0.067(3) 0.067(3) -0.015(2) 0.010(2) -0.007(2) 
C3 0.047(3) 0.054(3) 0.071(3) -0.009(3) 0.004(2) -0.003(2) 
C4 0.073(4) 0.066(4) 0.074(4) -0.022(3) 0.000(3) -0.001(3) 
C5 0.070(4) 0.060(3) 0.102(5) -0.008(4) -0.005(3) 0.000(3) 
C6 0.078(4) 0.061(4) 0.093(4) 0.006(3) 0.000(3) -0.007(3) 
C7 0.067(3) 0.068(4) 0.072(4) 0.003(3) -0.002(3) -0.002(3) 
C8 0.047(3) 0.058(3) 0.062(3) -0.006(3) -0.003(2) -0.003(3) 
C9 0.049(3) 0.061(3) 0.064(3) -0.007(3) -0.005(2) 0.002(2) 
C10 0.049(3) 0.055(3) 0.067(3) -0.001(3) -0.002(2) 0.002(2) 
C11 0.049(3) 0.062(3) 0.077(3) -0.012(3) -0.002(2) -0.001(3) 
N12 0.054(2) 0.045(2) 0.078(3) -0.007(2) -0.013(2) -0.002(2) 
C13 0.058(3) 0.049(3) 0.087(4) -0.008(3) -0.003(3) 0.006(3) 
O14 0.117(3) 0.040(2) 0.138(4) -0.009(2) -0.021(3) 0.002(2) 
C15 0.081(4) 0.082(4) 0.084(4) -0.010(4) -0.013(3) 0.008(3) 
C16 0.050(3) 0.064(3) 0.062(3) -0.008(3) 0.002(2) -0.004(3) 
C17 0.059(3) 0.082(4) 0.085(4) 0.012(3) 0.006(3) 0.003(3) 
C18 0.061(3) 0.092(4) 0.089(4) 0.006(4) 0.021(3) 0.006(3) 
C19 0.059(3) 0.076(4) 0.080(4) 0.001(3) 0.004(3) -0.014(3) 
C20 0.060(3) 0.063(3) 0.077(3) -0.002(3) -0.008(3) -0.002(3) 
C21 0.048(3) 0.059(3) 0.069(3) -0.005(3) 0.001(2) 0.002(3) 
O22 0.074(3) 0.114(4) 0.114(3) 0.039(3) 0.016(2) -0.011(3) 
C23 0.104(5) 0.157(8) 0.117(6) 0.065(6) 0.003(5) -0.010(5) 
N24 0.045(2) 0.070(3) 0.081(3) -0.023(2) 0.003(2) 0.002(2) 
C25 0.052(3) 0.051(3) 0.058(3) -0.002(3) 0.008(2) -0.002(2) 
C26 0.063(3) 0.062(3) 0.067(3) -0.010(3) 0.003(3) -0.004(3) 
C27 0.089(4) 0.058(3) 0.064(3) -0.001(3) 0.000(3) -0.013(3) 
C28 0.096(5) 0.059(4) 0.077(4) -0.003(3) 0.022(3) 0.013(4) 
C29 0.070(3) 0.067(4) 0.087(4) 0.000(4) 0.010(3) 0.012(3) 
C30 0.052(3) 0.067(3) 0.067(3) 0.000(3) 0.002(2) 0.000(3) 

_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 
C1 N2 1.447(6) . ? 
C1 C16 1.518(7) . ? 
C1 C10 1.531(6) . ? 
N2 C3 1.386(6) . ? 
C3 C4 1.381(7) . ? 
C3 C8 1.401(7) . ? 
C4 C5 1.372(8) . ? 
C5 C6 1.371(8) . ? 
C6 C7 1.372(7) . ? 
C7 C8 1.386(7) . ? 
C8 C9 1.515(7) . ? 
C9 N24 1.470(6) . ? 
C9 C10 1.542(6) . ? 
C10 C11 1.543(6) . ? 
C11 N12 1.447(6) . ? 
N12 C13 1.328(6) . ? 
C13 O14 1.220(6) . ? 
C13 C15 1.499(7) . ? 
C16 C21 1.384(7) . ? 
C16 C17 1.398(7) . ? 
C17 C18 1.378(7) . ? 
C18 C19 1.382(8) . ? 
C19 C20 1.382(7) . ? 
C19 O22 1.386(6) . ? 
C20 C21 1.369(7) . ? 
O22 C23 1.419(7) . ? 
N24 C25 1.375(6) . ? 
C25 C30 1.395(7) . ? 
C25 C26 1.397(7) . ? 
C26 C27 1.379(7) . ? 
C27 C28 1.381(7) . ? 
C28 C29 1.380(8) . ? 
C29 C30 1.373(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 
N2 C1 C16 110.7(4) . . ? 
N2 C1 C10 108.9(4) . . ? 
C16 C1 C10 117.0(4) . . ? 
C3 N2 C1 119.0(4) . . ? 
C4 C3 N2 120.7(5) . . ? 
C4 C3 C8 119.1(5) . . ? 
N2 C3 C8 120.2(4) . . ? 
C5 C4 C3 120.7(5) . . ? 
C6 C5 C4 121.3(6) . . ? 
C5 C6 C7 118.2(6) . . ? 
C6 C7 C8 122.3(5) . . ? 
C7 C8 C3 118.5(5) . . ? 
C7 C8 C9 120.4(4) . . ? 
C3 C8 C9 121.1(5) . . ? 
N24 C9 C8 108.2(4) . . ? 
N24 C9 C10 112.1(4) . . ? 
C8 C9 C10 111.4(4) . . ? 
C1 C10 C9 108.1(4) . . ? 
C1 C10 C11 113.2(4) . . ? 
C9 C10 C11 111.2(4) . . ? 
N12 C11 C10 111.5(4) . . ? 
C13 N12 C11 124.4(4) . . ? 
O14 C13 N12 123.0(5) . . ? 
O14 C13 C15 121.0(5) . . ? 
N12 C13 C15 116.0(5) . . ? 
C21 C16 C17 117.7(5) . . ? 
C21 C16 C1 119.6(4) . . ? 
C17 C16 C1 122.6(5) . . ? 
C18 C17 C16 120.5(5) . . ? 
C17 C18 C19 120.6(5) . . ? 
C20 C19 C18 119.2(5) . . ? 
C20 C19 O22 124.7(6) . . ? 
C18 C19 O22 116.1(5) . . ? 
C21 C20 C19 119.9(5) . . ? 
C20 C21 C16 122.0(5) . . ? 
C19 O22 C23 117.0(5) . . ? 
C25 N24 C9 125.4(4) . . ? 
N24 C25 C30 119.2(4) . . ? 
N24 C25 C26 123.2(4) . . ? 
C30 C25 C26 117.5(5) . . ? 
C27 C26 C25 120.2(5) . . ? 
C26 C27 C28 121.5(5) . . ? 
C29 C28 C27 118.7(5) . . ? 
C30 C29 C28 120.3(5) . . ? 
C29 C30 C25 121.7(5) . . ? 

_diffrn_measured_fraction_theta_max    0.984 
_diffrn_reflns_theta_full              54.98 
_diffrn_measured_fraction_theta_full   0.984 
_refine_diff_density_max    0.212 
_refine_diff_density_min   -0.272 
_refine_diff_density_rms    0.064