# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2003

data_global

_journal_coden_Cambridge         222

loop_
_publ_author_name
;
Peter O'Brien
;
'Michael J. Dearden'
'John Gilday'
'Justin R. Harrison'
'Jean-Paul R. Hermet'
'Tobias Koplin'
'Jerome Parmene'
'David W. Porter'
'Neil M. Smith'
'Vladimir Tyurin'
'Adrian C. Whitwood'

_publ_contact_author_name        
;
Dr Peter O'Brien
;
_publ_contact_author_address     
;
Department of Chemistry
University of York
Heslington
York
YO10 5DD
UNITED KINGDOM
;

_publ_contact_author_email       PAOB1@YORK.AC.UK

_publ_requested_journal          'Dalton Transactions'

_publ_section_title              
;
Synthesis of sparteine-like chiral diamines and
evaluation in the enantioselective lithiation-substitution of
N-(tert-butoxycarbonyl)pyrrolidine
;

data_pob0301m
_database_code_CSD               215917

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H20 N2 O3'
_chemical_formula_sum            'C13 H20 N2 O3'
_chemical_formula_weight         252.31

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           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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'

_cell_length_a                   7.9103(4)
_cell_length_b                   9.9556(5)
_cell_length_c                   15.8702(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1249.81(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    115(2)
_cell_measurement_reflns_used    4906
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      30.0

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS v2.03; (Sheldrick)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      115(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 SMART CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10029
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         30.03
_reflns_number_total             3598
_reflns_number_gt                3370
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART v5.625 (Bruker)'
_computing_cell_refinement       'SAINT+ v6.22 (Bruker)'
_computing_data_reduction        'SAINT+ v6.22 (Bruker)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHELL v4.02 (Bruker)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² 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/[σ²(Fo²)+(0.0594P)²+0.0636P] where P=(Fo²+2Fc²)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(7)
_refine_ls_number_reflns         3598
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0898
_refine_ls_wR_factor_gt          0.0877
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.81469(10) 0.39545(8) 0.89736(5) 0.01515(16) Uani 1 1 d . . .
O1 O 0.76092(11) 0.46919(8) 1.02948(5) 0.02707(18) Uani 1 1 d . . .
O3 O 0.48558(11) 0.67168(8) 0.89398(5) 0.02691(18) Uani 1 1 d . . .
N2 N 0.60116(10) 0.55181(9) 0.78972(6) 0.02028(18) Uani 1 1 d . . .
O2 O 0.37018(10) 0.47122(8) 0.85883(5) 0.02728(18) Uani 1 1 d . . .
C5 C 0.80778(12) 0.29376(10) 0.82991(6) 0.01633(18) Uani 1 1 d . . .
H5 H 0.9210 0.2492 0.8282 0.020 Uiso 1 1 calc R . .
C4 C 0.67869(13) 0.18468(10) 0.84722(7) 0.0212(2) Uani 1 1 d . . .
H4A H 0.6982 0.1083 0.8085 0.025 Uiso 1 1 calc R . .
H4B H 0.5637 0.2200 0.8365 0.025 Uiso 1 1 calc R . .
C7 C 0.61261(13) 0.43585(11) 0.73366(6) 0.0214(2) Uani 1 1 d . . .
H7A H 0.6003 0.4661 0.6746 0.026 Uiso 1 1 calc R . .
H7B H 0.5188 0.3731 0.7462 0.026 Uiso 1 1 calc R . .
C9 C 0.91105(12) 0.57013(11) 0.79520(7) 0.02074(19) Uani 1 1 d . . .
H9 H 1.0053 0.6356 0.7866 0.025 Uiso 1 1 calc R . .
C10 C 0.93164(12) 0.50734(10) 0.88218(6) 0.01824(19) Uani 1 1 d . . .
H10A H 1.0491 0.4745 0.8883 0.022 Uiso 1 1 calc R . .
H10B H 0.9128 0.5773 0.9255 0.022 Uiso 1 1 calc R . .
C11 C 0.92515(13) 0.46171(12) 0.72803(6) 0.0237(2) Uani 1 1 d . . .
H11A H 1.0359 0.4159 0.7320 0.028 Uiso 1 1 calc R . .
H11B H 0.9146 0.5017 0.6712 0.028 Uiso 1 1 calc R . .
C1 C 0.74678(13) 0.38138(10) 0.97535(6) 0.01777(18) Uani 1 1 d . . .
C6 C 0.78173(12) 0.36202(11) 0.74372(6) 0.01980(19) Uani 1 1 d . . .
H6 H 0.7879 0.2910 0.6993 0.024 Uiso 1 1 calc R . .
C8 C 0.74294(13) 0.64572(11) 0.78541(7) 0.0245(2) Uani 1 1 d . . .
H8A H 0.7321 0.7135 0.8307 0.029 Uiso 1 1 calc R . .
H8B H 0.7411 0.6932 0.7306 0.029 Uiso 1 1 calc R . .
C3 C 0.69075(14) 0.13629(11) 0.93764(7) 0.0226(2) Uani 1 1 d . . .
H3A H 0.6092 0.0625 0.9475 0.027 Uiso 1 1 calc R . .
H3B H 0.8060 0.1023 0.9493 0.027 Uiso 1 1 calc R . .
C2 C 0.65094(14) 0.25393(12) 0.99480(7) 0.0257(2) Uani 1 1 d . . .
H2A H 0.5284 0.2731 0.9911 0.031 Uiso 1 1 calc R . .
H2B H 0.6757 0.2274 1.0536 0.031 Uiso 1 1 calc R . .
C12 C 0.47812(13) 0.55676(11) 0.84844(7) 0.02053(19) Uani 1 1 d . . .
C13 C 0.36709(19) 0.68334(13) 0.96200(8) 0.0347(3) Uani 1 1 d . . .
H13A H 0.4164 0.6450 1.0133 0.052 Uiso 1 1 calc R . .
H13B H 0.2633 0.6347 0.9477 0.052 Uiso 1 1 calc R . .
H13C H 0.3407 0.7783 0.9715 0.052 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 0.0165(3) 0.0153(3) 0.0137(3) -0.0002(3) 0.0005(3) -0.0019(3)
O1 0.0372(4) 0.0259(4) 0.0181(3) -0.0047(3) 0.0059(3) -0.0041(4)
O3 0.0314(4) 0.0211(4) 0.0282(4) -0.0031(3) 0.0044(3) -0.0017(3)
N2 0.0173(4) 0.0203(4) 0.0233(4) 0.0025(3) -0.0013(3) 0.0017(3)
O2 0.0243(4) 0.0263(4) 0.0313(4) -0.0043(3) 0.0052(3) -0.0044(3)
C5 0.0167(4) 0.0184(4) 0.0139(4) -0.0020(3) -0.0006(3) 0.0017(3)
C4 0.0211(5) 0.0197(4) 0.0228(5) -0.0017(4) -0.0036(4) -0.0028(4)
C7 0.0205(4) 0.0261(5) 0.0175(4) 0.0001(4) -0.0038(4) 0.0042(4)
C9 0.0169(4) 0.0231(5) 0.0223(4) 0.0074(4) 0.0019(4) -0.0018(4)
C10 0.0180(4) 0.0183(4) 0.0184(4) 0.0015(3) -0.0002(3) -0.0044(3)
C11 0.0204(5) 0.0338(6) 0.0168(4) 0.0060(4) 0.0033(3) 0.0018(4)
C1 0.0186(4) 0.0192(4) 0.0155(4) 0.0012(3) 0.0015(3) 0.0006(4)
C6 0.0190(4) 0.0263(5) 0.0141(4) -0.0008(3) -0.0001(3) 0.0031(4)
C8 0.0207(4) 0.0216(5) 0.0311(5) 0.0094(4) 0.0003(4) -0.0001(4)
C3 0.0239(5) 0.0189(4) 0.0251(5) 0.0028(4) -0.0010(4) -0.0049(4)
C2 0.0300(5) 0.0236(5) 0.0236(5) 0.0013(4) 0.0089(4) -0.0066(4)
C12 0.0201(4) 0.0208(4) 0.0207(4) 0.0017(4) -0.0029(4) 0.0030(4)
C13 0.0444(7) 0.0295(6) 0.0302(6) -0.0069(5) 0.0099(5) -0.0032(5)

_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 C1 1.3565(12) . ?
N1 C10 1.4679(12) . ?
N1 C5 1.4744(11) . ?
O1 C1 1.2308(12) . ?
O3 C12 1.3546(13) . ?
O3 C13 1.4343(15) . ?
N2 C12 1.3484(13) . ?
N2 C7 1.4604(13) . ?
N2 C8 1.4617(13) . ?
O2 C12 1.2171(13) . ?
C5 C4 1.5158(14) . ?
C5 C6 1.5412(13) . ?
C4 C3 1.5167(15) . ?
C7 C6 1.5347(14) . ?
C9 C11 1.5212(15) . ?
C9 C10 1.5240(14) . ?
C9 C8 1.5359(14) . ?
C11 C6 1.5277(15) . ?
C1 C2 1.5099(14) . ?
C3 C2 1.5146(16) . ?

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
C1 N1 C10 118.54(8) . . ?
C1 N1 C5 125.23(8) . . ?
C10 N1 C5 115.17(7) . . ?
C12 O3 C13 116.20(9) . . ?
C12 N2 C7 119.65(9) . . ?
C12 N2 C8 124.25(9) . . ?
C7 N2 C8 115.44(8) . . ?
N1 C5 C4 112.66(8) . . ?
N1 C5 C6 110.28(8) . . ?
C4 C5 C6 112.75(8) . . ?
C5 C4 C3 110.90(8) . . ?
N2 C7 C6 111.67(8) . . ?
C11 C9 C10 109.63(8) . . ?
C11 C9 C8 109.89(9) . . ?
C10 C9 C8 112.66(8) . . ?
N1 C10 C9 113.11(8) . . ?
C9 C11 C6 107.00(8) . . ?
O1 C1 N1 121.84(9) . . ?
O1 C1 C2 119.99(9) . . ?
N1 C1 C2 118.18(9) . . ?
C11 C6 C7 108.62(8) . . ?
C11 C6 C5 109.38(8) . . ?
C7 C6 C5 114.83(8) . . ?
N2 C8 C9 110.25(8) . . ?
C2 C3 C4 107.94(9) . . ?
C1 C2 C3 115.02(8) . . ?
O2 C12 N2 125.06(10) . . ?
O2 C12 O3 123.32(9) . . ?
N2 C12 O3 111.60(9) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        30.03
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.332 #[  0.74 A from C6 ]
_refine_diff_density_min         -0.183 #[  1.39 A from C4 ]
_refine_diff_density_rms         0.045



