Supplementary Material (ESI) for Perkin Transactions
This journal is © The Royal Society of Chemistry 2002


data_40
_database_code_CSD                  169151
_journal_coden_Cambridge      188

_publ_requested_journal       'Perkin Transactions 2'

loop_
_publ_author_name
'Atkinson, Robert S.'
'Claxton, T. A.'
'Fawcett, John'
'Lochrie, Ian'
'Ulukanli, Sabri'

_publ_contact_author_name     	'Dr Robert S Atkinson'  
_publ_contact_author_address 
;
Dr Robert S Atkinson
Department of Chemistry
Leicester University
Leicester
LE1 7RH
UNITED KINGDOM
;

_publ_contact_author_email       'VOW@LE.AC.UK'

_publ_section_title
;
Aziridination of B-Substituted Styrene Derivatives with
3-Acetoxyaminoquinazolin-4(3H0)-ones: Probing Transition State Goemetry from
Changes in Diastereoselectivity
;

_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          
'C23 H26 Cl N3 O'  
_chemical_formula_sum 
'C23 H26 Cl N3 O' 
_chemical_formula_weight          395.92 

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    P21/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                    9.750(9) 
_cell_length_b                    12.881(14) 
_cell_length_c                    16.715(9) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  95.70(6) 
_cell_angle_gamma                 90.00 
_cell_volume                      2089(3) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     200(2) 
_cell_measurement_reflns_used     13 
_cell_measurement_theta_min       4.69 
_cell_measurement_theta_max       16.97 

_exptl_crystal_description        block 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.56 
_exptl_crystal_size_mid           0.53 
_exptl_crystal_size_min           0.43 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.259 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              840 
_exptl_absorpt_coefficient_mu     0.201 
_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       200(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   'Bruker P4' 
_diffrn_measurement_method        '\w scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          3
_diffrn_standards_interval_count  97 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         <1 
_diffrn_reflns_number             3092 
_diffrn_reflns_av_R_equivalents   0.0206 
_diffrn_reflns_av_sigmaI/netI     0.0267 
_diffrn_reflns_limit_h_min        0 
_diffrn_reflns_limit_h_max        7 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        15 
_diffrn_reflns_limit_l_min        -19 
_diffrn_reflns_limit_l_max        19 
_diffrn_reflns_theta_min          2.63 
_diffrn_reflns_theta_max          25.03 
_reflns_number_total              2863 
_reflns_number_gt                 2156 
_reflns_threshold_expression      >2sigma(I) 

_computing_data_collection        'Bruker XSCANS' 
_computing_cell_refinement        'Bruker XSCANS' 
_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^)+(0.1470P)^2^+1.9645P] 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          2863 
_refine_ls_number_parameters      257 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0854 
_refine_ls_R_factor_gt            0.0558 
_refine_ls_wR_factor_ref          0.2373 
_refine_ls_wR_factor_gt           0.1686 
_refine_ls_goodness_of_fit_ref    1.072 
_refine_ls_restrained_S_all       1.072 
_refine_ls_shift/su_max           0.001 
_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 0.12687(15) 0.58203(9) 0.80875(10) 0.0677(6) Uani 1 1 d . . . 
O1 O 0.0567(4) 0.9086(2) 0.89649(18) 0.0465(9) Uani 1 1 d . . . 
N1 N 0.3756(4) 1.0795(2) 0.82861(18) 0.0332(9) Uani 1 1 d . . . 
N2 N 0.2375(4) 0.8159(2) 0.81173(18) 0.0350(9) Uani 1 1 d . . . 
N3 N 0.2470(4) 0.9255(2) 0.82699(17) 0.0296(9) Uani 1 1 d . . . 
C1 C 0.4921(4) 0.9242(3) 0.7904(2) 0.0301(10) Uani 1 1 d . . . 
H1 H 0.4604 0.8573 0.7676 0.036 Uiso 1 1 calc R . . 
C2 C 0.3660(4) 0.9801(3) 0.8153(2) 0.0293(10) Uani 1 1 d . . . 
C3 C 0.5511(5) 0.9848(3) 0.7233(2) 0.0447(12) Uani 1 1 d . . . 
H3A H 0.5718 1.0544 0.7411 0.067 Uiso 1 1 calc R . . 
H3B H 0.4848 0.9865 0.6768 0.067 Uiso 1 1 calc R . . 
H3C H 0.6338 0.9516 0.7097 0.067 Uiso 1 1 calc R . . 
C4 C 0.1455(5) 0.9642(3) 0.8727(2) 0.0343(11) Uani 1 1 d . . . 
C5 C 0.1549(5) 1.0760(3) 0.8855(2) 0.0344(11) Uani 1 1 d . . . 
C6 C 0.0538(5) 1.1282(3) 0.9230(2) 0.0408(11) Uani 1 1 d . . . 
H6 H -0.0183 1.0913 0.9420 0.049 Uiso 1 1 calc R . . 
C7 C 0.0604(6) 1.2347(3) 0.9321(3) 0.0484(13) Uani 1 1 d . . . 
H7 H -0.0076 1.2698 0.9566 0.058 Uiso 1 1 calc R . . 
C8 C 0.1695(6) 1.2891(3) 0.9043(3) 0.0486(14) Uani 1 1 d . . . 
H8 H 0.1723 1.3610 0.9088 0.058 Uiso 1 1 calc R . . 
C9 C 0.2734(5) 1.2380(3) 0.8701(2) 0.0438(12) Uani 1 1 d . . . 
H9 H 0.3472 1.2752 0.8534 0.053 Uiso 1 1 calc R . . 
C10 C 0.2675(5) 1.1294(3) 0.8605(2) 0.0362(11) Uani 1 1 d . . . 
C11 C 0.5980(5) 0.9001(3) 0.8649(2) 0.0397(12) Uani 1 1 d . . . 
C12 C 0.5233(6) 0.8546(4) 0.9322(3) 0.0615(15) Uani 1 1 d . . . 
H12A H 0.4660 0.9069 0.9527 0.092 Uiso 1 1 calc R . . 
H12B H 0.5895 0.8308 0.9746 0.092 Uiso 1 1 calc R . . 
H12C H 0.4671 0.7974 0.9119 0.092 Uiso 1 1 calc R . . 
C13 C 0.7011(6) 0.8204(4) 0.8406(3) 0.0594(15) Uani 1 1 d . . . 
H13A H 0.6527 0.7601 0.8190 0.089 Uiso 1 1 calc R . . 
H13B H 0.7620 0.8009 0.8869 0.089 Uiso 1 1 calc R . . 
H13C H 0.7537 0.8497 0.8006 0.089 Uiso 1 1 calc R . . 
C14 C 0.6776(5) 0.9972(4) 0.8956(3) 0.0530(14) Uani 1 1 d . . . 
H14A H 0.7395 0.9796 0.9419 0.079 Uiso 1 1 calc R . . 
H14B H 0.6138 1.0491 0.9101 0.079 Uiso 1 1 calc R . . 
H14C H 0.7293 1.0238 0.8541 0.079 Uiso 1 1 calc R . . 
C15 C 0.0273(5) 0.6980(3) 0.8014(3) 0.0409(12) Uani 1 1 d . . . 
H15A H -0.0567 0.6855 0.7666 0.049 Uiso 1 1 calc R . . 
H15B H 0.0015 0.7158 0.8543 0.049 Uiso 1 1 calc R . . 
C16 C 0.1015(5) 0.7876(3) 0.7694(2) 0.0364(11) Uani 1 1 d . . . 
H16 H 0.0421 0.8476 0.7553 0.044 Uiso 1 1 calc R . . 
C17 C 0.2240(5) 0.7825(3) 0.7237(2) 0.0389(12) Uani 1 1 d . . . 
H17 H 0.2556 0.7113 0.7164 0.047 Uiso 1 1 calc R . . 
C18 C 0.2460(5) 0.8509(3) 0.6546(2) 0.0368(11) Uani 1 1 d . . . 
C19 C 0.3349(5) 0.8148(3) 0.5995(2) 0.0477(13) Uani 1 1 d . . . 
H19 H 0.3770 0.7503 0.6073 0.057 Uiso 1 1 calc R . . 
C20 C 0.3603(6) 0.8739(4) 0.5340(3) 0.0638(16) Uani 1 1 d . . . 
H20 H 0.4188 0.8492 0.4976 0.077 Uiso 1 1 calc R . . 
C21 C 0.2986(7) 0.9702(4) 0.5224(3) 0.0680(17) Uani 1 1 d . . . 
H21 H 0.3153 1.0102 0.4781 0.082 Uiso 1 1 calc R . . 
C22 C 0.2132(6) 1.0066(4) 0.5759(3) 0.0605(15) Uani 1 1 d . . . 
H22 H 0.1741 1.0722 0.5684 0.073 Uiso 1 1 calc R . . 
C23 C 0.1840(5) 0.9472(3) 0.6414(2) 0.0443(12) Uani 1 1 d . . . 
H23 H 0.1230 0.9719 0.6764 0.053 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 
Cl1 0.0525(13) 0.0379(6) 0.1159(12) 0.0213(6) 0.0244(8) 0.0042(6) 
O1 0.052(3) 0.0391(16) 0.0517(17) -0.0055(13) 0.0214(15) -0.0105(16) 
N1 0.037(3) 0.0278(16) 0.0338(16) 0.0012(12) -0.0001(15) -0.0024(15) 
N2 0.043(3) 0.0252(15) 0.0365(17) -0.0018(12) 0.0020(16) -0.0022(14) 
N3 0.032(3) 0.0247(15) 0.0327(16) -0.0009(12) 0.0044(15) -0.0026(15) 
C1 0.023(3) 0.0307(19) 0.0362(19) -0.0018(14) 0.0001(17) -0.0056(17) 
C2 0.029(3) 0.0322(19) 0.0263(17) 0.0032(14) -0.0007(16) -0.0021(18) 
C3 0.057(4) 0.042(2) 0.036(2) 0.0019(17) 0.007(2) -0.008(2) 
C4 0.037(3) 0.034(2) 0.0327(19) -0.0012(15) 0.0045(18) -0.003(2) 
C5 0.041(3) 0.0317(19) 0.0286(18) -0.0005(14) -0.0053(18) -0.0011(19) 
C6 0.042(3) 0.043(2) 0.036(2) -0.0028(17) -0.0001(19) 0.005(2) 
C7 0.058(4) 0.039(2) 0.046(2) -0.0094(18) -0.008(2) 0.011(2) 
C8 0.068(4) 0.028(2) 0.045(2) -0.0090(17) -0.017(2) 0.009(2) 
C9 0.060(4) 0.0281(19) 0.041(2) 0.0003(16) -0.007(2) -0.003(2) 
C10 0.049(4) 0.0294(19) 0.0283(18) 0.0012(15) -0.0050(18) 0.003(2) 
C11 0.037(3) 0.040(2) 0.040(2) -0.0022(16) -0.0069(19) -0.0003(19) 
C12 0.074(4) 0.064(3) 0.043(2) 0.020(2) -0.013(2) -0.010(3) 
C13 0.049(4) 0.065(3) 0.061(3) -0.012(2) -0.005(3) 0.021(3) 
C14 0.050(4) 0.052(3) 0.052(3) -0.006(2) -0.016(2) -0.003(2) 
C15 0.024(3) 0.039(2) 0.061(3) -0.0045(18) 0.010(2) -0.0027(19) 
C16 0.035(3) 0.0307(19) 0.043(2) -0.0062(16) 0.001(2) -0.0017(18) 
C17 0.054(4) 0.0218(18) 0.039(2) -0.0054(15) -0.007(2) 0.0013(18) 
C18 0.040(3) 0.0303(19) 0.038(2) -0.0075(15) -0.0070(19) 0.0023(18) 
C19 0.061(4) 0.035(2) 0.045(2) -0.0070(18) -0.002(2) 0.011(2) 
C20 0.091(5) 0.057(3) 0.044(3) -0.003(2) 0.010(3) 0.021(3) 
C21 0.097(5) 0.070(3) 0.037(2) 0.015(2) 0.010(3) 0.023(3) 
C22 0.085(5) 0.052(3) 0.044(2) 0.010(2) 0.002(3) 0.026(3) 
C23 0.048(4) 0.041(2) 0.043(2) -0.0013(17) -0.002(2) 0.013(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 
Cl1 C15 1.779(5) . ? 
O1 C4 1.219(5) . ? 
N1 C2 1.301(5) . ? 
N1 C10 1.385(5) . ? 
N2 N3 1.437(4) . ? 
N2 C16 1.485(6) . ? 
N2 C17 1.525(5) . ? 
N3 C2 1.388(5) . ? 
N3 C4 1.401(5) . ? 
C1 C2 1.518(6) . ? 
C1 C3 1.525(5) . ? 
C1 C11 1.568(5) . ? 
C4 C5 1.457(5) . ? 
C5 C6 1.394(6) . ? 
C5 C10 1.395(6) . ? 
C6 C7 1.380(6) . ? 
C7 C8 1.392(7) . ? 
C8 C9 1.379(7) . ? 
C9 C10 1.408(5) . ? 
C11 C12 1.517(7) . ? 
C11 C13 1.520(6) . ? 
C11 C14 1.534(6) . ? 
C15 C16 1.490(6) . ? 
C16 C17 1.481(6) . ? 
C17 C18 1.486(6) . ? 
C18 C23 1.388(6) . ? 
C18 C19 1.405(6) . ? 
C19 C20 1.376(7) . ? 
C20 C21 1.384(7) . ? 
C21 C22 1.364(7) . ? 
C22 C23 1.388(6) . ? 

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 
C2 N1 C10 118.6(4) . . ? 
N3 N2 C16 111.4(3) . . ? 
N3 N2 C17 116.5(3) . . ? 
C16 N2 C17 58.9(3) . . ? 
C2 N3 C4 122.9(3) . . ? 
C2 N3 N2 120.9(3) . . ? 
C4 N3 N2 114.2(3) . . ? 
C2 C1 C3 109.5(3) . . ? 
C2 C1 C11 111.3(3) . . ? 
C3 C1 C11 114.8(4) . . ? 
N1 C2 N3 121.4(4) . . ? 
N1 C2 C1 117.9(4) . . ? 
N3 C2 C1 120.7(3) . . ? 
O1 C4 N3 122.2(4) . . ? 
O1 C4 C5 124.6(4) . . ? 
N3 C4 C5 113.2(4) . . ? 
C6 C5 C10 120.6(4) . . ? 
C6 C5 C4 120.4(4) . . ? 
C10 C5 C4 119.0(4) . . ? 
C7 C6 C5 120.2(5) . . ? 
C6 C7 C8 119.5(5) . . ? 
C9 C8 C7 121.0(4) . . ? 
C8 C9 C10 119.9(5) . . ? 
N1 C10 C5 122.5(4) . . ? 
N1 C10 C9 118.8(4) . . ? 
C5 C10 C9 118.7(4) . . ? 
C12 C11 C13 108.4(4) . . ? 
C12 C11 C14 109.3(4) . . ? 
C13 C11 C14 108.3(4) . . ? 
C12 C11 C1 109.8(4) . . ? 
C13 C11 C1 108.8(3) . . ? 
C14 C11 C1 112.0(3) . . ? 
C16 C15 Cl1 113.2(3) . . ? 
C17 C16 N2 61.9(3) . . ? 
C17 C16 C15 126.6(3) . . ? 
N2 C16 C15 117.4(3) . . ? 
C16 C17 C18 124.1(4) . . ? 
C16 C17 N2 59.2(3) . . ? 
C18 C17 N2 125.3(3) . . ? 
C23 C18 C19 118.6(4) . . ? 
C23 C18 C17 124.0(4) . . ? 
C19 C18 C17 117.4(4) . . ? 
C20 C19 C18 120.7(4) . . ? 
C19 C20 C21 119.8(5) . . ? 
C22 C21 C20 120.1(5) . . ? 
C21 C22 C23 120.9(4) . . ? 
C22 C23 C18 119.8(4) . . ? 

_diffrn_measured_fraction_theta_max    0.776 
_diffrn_reflns_theta_full              25.03 
_diffrn_measured_fraction_theta_full   0.776 
_refine_diff_density_max    0.311 
_refine_diff_density_min   -0.454 
_refine_diff_density_rms    0.076