# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2001


data_sl0123 

_database_code_CSD	174514


_journal_coden_Cambridge      207

_publ_requested_journal       'Perkin Transactions 1'

loop_
_publ_author_name
'Ley, S.'
'Baxendale, Ian R.'
'Brusotti, Gloria'
'Matsuoka, M.'

_publ_contact_author_name     	'Prof S Ley'  
_publ_contact_author_address 
;
University Chemical Laboratory
Lensfield Road
Cambridge
CB2 1EW
UK
;

_publ_contact_author_email       'SV11000@CAM.AC.UK'

_publ_section_title		
;
Synthesis of nornicotine, nicotine and other functionalised
derivatives using solid-supported reagents and scavengers.
;


audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          
'C17 H20 N2 O'     
_chemical_formula_sum 
'C17 H20 N2 O' 
_chemical_formula_weight          268.35 

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) 

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

_cell_length_a                    8.9473(8) 
_cell_length_b                    6.0399(3) 
_cell_length_c                    13.4384(10) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  91.719(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      725.89(9) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     180(2) 
_cell_measurement_reflns_used     3326
_cell_measurement_theta_min       1.00
_cell_measurement_theta_max       27.48 

_exptl_crystal_description        ? 
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.35 
_exptl_crystal_size_mid           0.19 
_exptl_crystal_size_min           0.16 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.228 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              288 
_exptl_absorpt_coefficient_mu     0.077 
_exptl_absorpt_correction_type 'multiscan' 
_exptl_absorpt_process_details 'Sortav Blessing (1995) ' 
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_process_details 
;
multi-scan from symmetry-related measurements (Blessing 1995)
;


_exptl_special_details 
; 
? 
; 

_diffrn_ambient_temperature       180(2) 
_diffrn_radiation_wavelength      0.71069 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_measurement_device_type   'KappaCCD'
_diffrn_measurement_device        '95mm CCD camera on \k-goniostat'
_diffrn_detector_area_resol_mean  9
_diffrn_radiation_monochromator   'horizonally mounted graphite crystal'
_diffrn_measurement_method        'fine slice omega/phi scans'
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             5004 
_diffrn_reflns_av_R_equivalents   0.0391 
_diffrn_reflns_av_sigmaI/netI     0.0716 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -7 
_diffrn_reflns_limit_k_max        6 
_diffrn_reflns_limit_l_min        -17 
_diffrn_reflns_limit_l_max        17 
_diffrn_reflns_theta_min          3.70 
_diffrn_reflns_theta_max          27.45 
_reflns_number_total              2945 
_reflns_number_gt                 2048 
_reflns_threshold_expression      >2sigma(I) 

_computing_data_collection       'Collect (Nonius BV, 1997-2000)' 
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution     
;
TEXSAN: Molecular Structure Corporation (1995). Version 1.7. 
MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA'
;
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 

_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^)+(0.0589P)^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     mixed 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.082(8) 
_refine_ls_extinction_expression 
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    -2(2) 
_refine_ls_number_reflns          2945 
_refine_ls_number_parameters      185 
_refine_ls_number_restraints      2 
_refine_ls_R_factor_all           0.0850 
_refine_ls_R_factor_gt            0.0501 
_refine_ls_wR_factor_ref          0.1177 
_refine_ls_wR_factor_gt           0.1040 
_refine_ls_goodness_of_fit_ref    1.007 
_refine_ls_restrained_S_all       1.007 
_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 0.81747(19) 0.3334(3) 0.65534(13) 0.0337(5) Uani 1 1 d . . . 
C2 C 0.7363(2) 0.5302(4) 0.61491(16) 0.0363(6) Uani 1 1 d . . . 
H2 H 0.8055 0.6602 0.6160 0.044 Uiso 1 1 calc R . . 
C3 C 0.6960(3) 0.4693(5) 0.50544(17) 0.0605(8) Uani 1 1 d . . . 
H3A H 0.5861 0.4647 0.4942 0.073 Uiso 1 1 calc R . . 
H3B H 0.7385 0.5787 0.4593 0.073 Uiso 1 1 calc R . . 
C4 C 0.7637(3) 0.2426(5) 0.4898(2) 0.0632(8) Uani 1 1 d . . . 
H4A H 0.6889 0.1242 0.4991 0.076 Uiso 1 1 calc R . . 
H4B H 0.8044 0.2294 0.4223 0.076 Uiso 1 1 calc R . . 
C5 C 0.8867(3) 0.2310(4) 0.56866(18) 0.0456(6) Uani 1 1 d . . . 
H5A H 0.9159 0.0758 0.5827 0.055 Uiso 1 1 calc R . . 
H5B H 0.9758 0.3151 0.5486 0.055 Uiso 1 1 calc R . . 
C6 C 0.9259(2) 0.3881(3) 0.73594(17) 0.0347(6) Uani 1 1 d . . . 
H6 H 0.9949 0.5048 0.7112 0.042 Uiso 1 1 calc R . . 
C7 C 1.0193(3) 0.1877(5) 0.7677(2) 0.0489(7) Uani 1 1 d . . . 
H7A H 1.0588 0.2134 0.8364 0.059 Uiso 1 1 calc R . . 
H7B H 0.9526 0.0571 0.7697 0.059 Uiso 1 1 calc R . . 
O8 O 1.1396(2) 0.1369(3) 0.70739(15) 0.0605(5) Uani 1 1 d D . . 
H8 H 1.218(3) 0.250(4) 0.726(2) 0.073 Uiso 1 1 d D . . 
N1' N 0.3682(2) 0.4606(4) 0.74155(14) 0.0454(5) Uani 1 1 d . . . 
C2' C 0.4909(2) 0.4273(4) 0.68922(17) 0.0387(6) Uani 1 1 d . . . 
H2' H 0.5038 0.2858 0.6599 0.046 Uiso 1 1 calc R . . 
C3' C 0.6007(2) 0.5853(4) 0.67477(15) 0.0340(5) Uani 1 1 d . . . 
C4' C 0.5792(3) 0.7915(4) 0.71636(17) 0.0412(6) Uani 1 1 d . . . 
H4' H 0.6507 0.9057 0.7080 0.049 Uiso 1 1 calc R . . 
C5' C 0.4521(3) 0.8305(5) 0.77037(19) 0.0515(7) Uani 1 1 d . . . 
H5' H 0.4347 0.9717 0.7989 0.062 Uiso 1 1 calc R . . 
C6' C 0.3525(3) 0.6612(5) 0.78170(18) 0.0507(7) Uani 1 1 d . . . 
H6' H 0.2672 0.6879 0.8204 0.061 Uiso 1 1 calc R . . 
C1" C 0.8511(2) 0.4764(4) 0.82772(16) 0.0336(5) Uani 1 1 d . . . 
C2" C 0.7370(3) 0.3603(4) 0.87301(17) 0.0427(6) Uani 1 1 d . . . 
H2" H 0.7019 0.2254 0.8445 0.051 Uiso 1 1 calc R . . 
C3" C 0.6740(3) 0.4388(5) 0.95892(18) 0.0540(7) Uani 1 1 d . . . 
H3" H 0.5959 0.3582 0.9887 0.065 Uiso 1 1 calc R . . 
C4" C 0.7245(3) 0.6341(5) 1.00148(19) 0.0568(7) Uani 1 1 d . . . 
H4" H 0.6801 0.6892 1.0598 0.068 Uiso 1 1 calc R . . 
C5" C 0.8394(3) 0.7487(4) 0.95913(19) 0.0523(7) Uani 1 1 d . . . 
H5" H 0.8750 0.8826 0.9884 0.063 Uiso 1 1 calc R . . 
C6" C 0.9029(3) 0.6681(4) 0.87371(18) 0.0413(6) Uani 1 1 d . . . 
H6" H 0.9840 0.7460 0.8460 0.050 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 0.0299(10) 0.0364(11) 0.0348(10) 0.0010(8) 0.0012(8) 0.0025(8) 
C2 0.0304(12) 0.0454(15) 0.0332(13) 0.0065(10) 0.0036(10) 0.0045(10) 
C3 0.0443(15) 0.104(2) 0.0336(14) 0.0091(15) 0.0034(12) 0.0153(16) 
C4 0.0540(18) 0.092(2) 0.0439(16) -0.0171(15) 0.0011(14) 0.0069(16) 
C5 0.0409(14) 0.0497(16) 0.0463(15) -0.0115(12) 0.0053(12) 0.0016(11) 
C6 0.0290(11) 0.0354(15) 0.0395(13) 0.0053(10) -0.0016(10) -0.0041(9) 
C7 0.0373(14) 0.0547(17) 0.0545(16) 0.0086(12) -0.0014(12) 0.0090(12) 
O8 0.0390(10) 0.0649(14) 0.0772(14) -0.0138(10) -0.0034(9) 0.0162(9) 
N1' 0.0301(11) 0.0645(15) 0.0414(11) 0.0003(11) -0.0002(9) 0.0035(10) 
C2' 0.0287(12) 0.0482(15) 0.0391(13) 0.0031(11) -0.0002(10) 0.0036(10) 
C3' 0.0322(13) 0.0385(14) 0.0311(13) 0.0051(10) -0.0020(10) 0.0066(10) 
C4' 0.0379(14) 0.0422(15) 0.0431(13) 0.0021(11) -0.0046(11) 0.0039(11) 
C5' 0.0490(16) 0.0559(17) 0.0496(15) -0.0114(13) -0.0002(13) 0.0121(14) 
C6' 0.0381(14) 0.0735(19) 0.0406(15) -0.0071(13) 0.0039(11) 0.0139(14) 
C1" 0.0283(12) 0.0409(13) 0.0314(11) 0.0084(10) -0.0045(9) -0.0004(10) 
C2" 0.0418(14) 0.0508(15) 0.0352(13) 0.0048(11) -0.0053(11) -0.0126(11) 
C3" 0.0457(15) 0.081(2) 0.0354(13) 0.0055(13) 0.0018(11) -0.0131(14) 
C4" 0.0549(17) 0.078(2) 0.0370(15) -0.0046(14) 0.0006(13) 0.0006(15) 
C5" 0.0627(17) 0.0510(16) 0.0426(15) -0.0041(12) -0.0090(14) 0.0002(13) 
C6" 0.0395(13) 0.0391(14) 0.0449(14) 0.0088(11) -0.0051(11) -0.0023(11) 

_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 C6 1.470(3) . ? 
N1 C5 1.472(3) . ? 
N1 C2 1.487(3) . ? 
C2 C3' 1.512(3) . ? 
C2 C3 1.549(3) . ? 
C2 H2 1.0000 . ? 
C3 C4 1.515(4) . ? 
C3 H3A 0.9900 . ? 
C3 H3B 0.9900 . ? 
C4 C5 1.506(4) . ? 
C4 H4A 0.9900 . ? 
C4 H4B 0.9900 . ? 
C5 H5A 0.9900 . ? 
C5 H5B 0.9900 . ? 
C6 C1" 1.518(3) . ? 
C6 C7 1.525(3) . ? 
C6 H6 1.0000 . ? 
C7 O8 1.401(3) . ? 
C7 H7A 0.9900 . ? 
C7 H7B 0.9900 . ? 
O8 H8 1.006(17) . ? 
N1' C6' 1.336(4) . ? 
N1' C2' 1.336(3) . ? 
C2' C3' 1.388(3) . ? 
C2' H2' 0.9500 . ? 
C3' C4' 1.381(3) . ? 
C4' C5' 1.387(3) . ? 
C4' H4' 0.9500 . ? 
C5' C6' 1.368(4) . ? 
C5' H5' 0.9500 . ? 
C6' H6' 0.9500 . ? 
C1" C6" 1.386(3) . ? 
C1" C2" 1.393(3) . ? 
C2" C3" 1.384(3) . ? 
C2" H2" 0.9500 . ? 
C3" C4" 1.381(4) . ? 
C3" H3" 0.9500 . ? 
C4" C5" 1.377(4) . ? 
C4" H4" 0.9500 . ? 
C5" C6" 1.384(4) . ? 
C5" H5" 0.9500 . ? 
C6" H6" 0.9500 . ? 

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 
C6 N1 C5 113.19(16) . . ? 
C6 N1 C2 113.20(17) . . ? 
C5 N1 C2 105.03(17) . . ? 
N1 C2 C3' 111.85(17) . . ? 
N1 C2 C3 104.73(19) . . ? 
C3' C2 C3 112.95(19) . . ? 
N1 C2 H2 109.1 . . ? 
C3' C2 H2 109.1 . . ? 
C3 C2 H2 109.1 . . ? 
C4 C3 C2 105.3(2) . . ? 
C4 C3 H3A 110.7 . . ? 
C2 C3 H3A 110.7 . . ? 
C4 C3 H3B 110.7 . . ? 
C2 C3 H3B 110.7 . . ? 
H3A C3 H3B 108.8 . . ? 
C5 C4 C3 103.4(2) . . ? 
C5 C4 H4A 111.1 . . ? 
C3 C4 H4A 111.1 . . ? 
C5 C4 H4B 111.1 . . ? 
C3 C4 H4B 111.1 . . ? 
H4A C4 H4B 109.1 . . ? 
N1 C5 C4 102.82(19) . . ? 
N1 C5 H5A 111.2 . . ? 
C4 C5 H5A 111.2 . . ? 
N1 C5 H5B 111.2 . . ? 
C4 C5 H5B 111.2 . . ? 
H5A C5 H5B 109.1 . . ? 
N1 C6 C1" 112.37(17) . . ? 
N1 C6 C7 111.86(18) . . ? 
C1" C6 C7 107.60(18) . . ? 
N1 C6 H6 108.3 . . ? 
C1" C6 H6 108.3 . . ? 
C7 C6 H6 108.3 . . ? 
O8 C7 C6 115.8(2) . . ? 
O8 C7 H7A 108.3 . . ? 
C6 C7 H7A 108.3 . . ? 
O8 C7 H7B 108.3 . . ? 
C6 C7 H7B 108.3 . . ? 
H7A C7 H7B 107.4 . . ? 
C7 O8 H8 104.3(15) . . ? 
C6' N1' C2' 116.5(2) . . ? 
N1' C2' C3' 124.5(2) . . ? 
N1' C2' H2' 117.7 . . ? 
C3' C2' H2' 117.7 . . ? 
C4' C3' C2' 117.1(2) . . ? 
C4' C3' C2 122.5(2) . . ? 
C2' C3' C2 120.4(2) . . ? 
C3' C4' C5' 119.4(2) . . ? 
C3' C4' H4' 120.3 . . ? 
C5' C4' H4' 120.3 . . ? 
C6' C5' C4' 118.6(2) . . ? 
C6' C5' H5' 120.7 . . ? 
C4' C5' H5' 120.7 . . ? 
N1' C6' C5' 123.8(2) . . ? 
N1' C6' H6' 118.1 . . ? 
C5' C6' H6' 118.1 . . ? 
C6" C1" C2" 117.7(2) . . ? 
C6" C1" C6 120.4(2) . . ? 
C2" C1" C6 121.7(2) . . ? 
C3" C2" C1" 121.0(2) . . ? 
C3" C2" H2" 119.5 . . ? 
C1" C2" H2" 119.5 . . ? 
C4" C3" C2" 120.1(3) . . ? 
C4" C3" H3" 119.9 . . ? 
C2" C3" H3" 119.9 . . ? 
C5" C4" C3" 119.8(2) . . ? 
C5" C4" H4" 120.1 . . ? 
C3" C4" H4" 120.1 . . ? 
C4" C5" C6" 119.8(3) . . ? 
C4" C5" H5" 120.1 . . ? 
C6" C5" H5" 120.1 . . ? 
C5" C6" C1" 121.5(2) . . ? 
C5" C6" H6" 119.2 . . ? 
C1" C6" H6" 119.2 . . ? 

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 
C6 N1 C2 C3' -85.6(2) . . . . ? 
C5 N1 C2 C3' 150.48(19) . . . . ? 
C6 N1 C2 C3 151.77(18) . . . . ? 
C5 N1 C2 C3 27.8(2) . . . . ? 
N1 C2 C3 C4 -2.3(3) . . . . ? 
C3' C2 C3 C4 -124.3(2) . . . . ? 
C2 C3 C4 C5 -23.1(3) . . . . ? 
C6 N1 C5 C4 -166.85(19) . . . . ? 
C2 N1 C5 C4 -42.9(2) . . . . ? 
C3 C4 C5 N1 40.6(3) . . . . ? 
C5 N1 C6 C1" -175.41(19) . . . . ? 
C2 N1 C6 C1" 65.2(2) . . . . ? 
C5 N1 C6 C7 -54.3(2) . . . . ? 
C2 N1 C6 C7 -173.62(17) . . . . ? 
N1 C6 C7 O8 80.6(3) . . . . ? 
C1" C6 C7 O8 -155.5(2) . . . . ? 
C6' N1' C2' C3' 0.2(3) . . . . ? 
N1' C2' C3' C4' -1.1(3) . . . . ? 
N1' C2' C3' C2 179.5(2) . . . . ? 
N1 C2 C3' C4' 124.7(2) . . . . ? 
C3 C2 C3' C4' -117.4(2) . . . . ? 
N1 C2 C3' C2' -55.9(3) . . . . ? 
C3 C2 C3' C2' 61.9(3) . . . . ? 
C2' C3' C4' C5' 0.6(3) . . . . ? 
C2 C3' C4' C5' 180.0(2) . . . . ? 
C3' C4' C5' C6' 0.7(3) . . . . ? 
C2' N1' C6' C5' 1.2(3) . . . . ? 
C4' C5' C6' N1' -1.7(4) . . . . ? 
N1 C6 C1" C6" -131.49(19) . . . . ? 
C7 C6 C1" C6" 104.9(2) . . . . ? 
N1 C6 C1" C2" 53.6(3) . . . . ? 
C7 C6 C1" C2" -70.0(2) . . . . ? 
C6" C1" C2" C3" 2.4(3) . . . . ? 
C6 C1" C2" C3" 177.4(2) . . . . ? 
C1" C2" C3" C4" -0.4(4) . . . . ? 
C2" C3" C4" C5" -1.1(4) . . . . ? 
C3" C4" C5" C6" 0.4(4) . . . . ? 
C4" C5" C6" C1" 1.7(4) . . . . ? 
C2" C1" C6" C5" -3.1(3) . . . . ? 
C6 C1" C6" C5" -178.1(2) . . . . ? 

_diffrn_measured_fraction_theta_max    0.955 
_diffrn_reflns_theta_full              27.45 
_diffrn_measured_fraction_theta_full   0.955 
_refine_diff_density_max    0.233 
_refine_diff_density_min   -0.210 
_refine_diff_density_rms    0.056