Supplementary Material for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2007

data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Janne Tonder'
'Jakob S. Grau'
'Masood Hosseini'
'Anthony Murray'
'Kasper K. Sorensen'
'Inger Sotofte'
'David Tanner'

_publ_contact_author_name        'Janne Tonder'
_publ_contact_author_address     
;
Department of Chemistry
Technical University of Denmark
Building 201
Kgs. Lyngby
DK-2800
DENMARK
;

_publ_contact_author_email       JANNE.TONDER@GMAIL.COM

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
Short and Efficient Diastereoselective
Synthesis of Pyrrolidinone-containing
Dipeptide Analogues
;

data_mah4
_database_code_depnum_ccdc_archive 'CCDC 642750'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C12H21N3O2,1.5H2O
_chemical_formula_sum            'C12 H24 N3 O3.50'
_chemical_formula_weight         266.34

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 42'
_symmetry_space_group_name_Hall  'P 4c'

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

_cell_length_a                   12.9386(8)
_cell_length_b                   12.9386(8)
_cell_length_c                   8.5628(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1433.48(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    20006
_cell_measurement_theta_min      1.57
_cell_measurement_theta_max      28.04

_exptl_crystal_description       ?
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8487
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20006
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         28.04
_reflns_number_total             1858
_reflns_number_gt                1779
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker AXS,1998)'
_computing_cell_refinement       'SAINT (Bruker AXS,1998)'
_computing_data_reduction        'SAINT (Bruker AXS,1998)'
_computing_structure_solution    'SHELXTL,ver.6.12 (Sheldrick,2001)'
_computing_structure_refinement  'SHELXTL,ver.6.12 (Sheldrick,2001)'
_computing_molecular_graphics    'SHELXTL,ver.6.12 (Sheldrick,2001)'
_computing_publication_material  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.
Friedel pairs were merged before refinement.
;

_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^)+(0.0487P)^2^+2.5178P] 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       ?
_chemical_absolute_configuration .
_refine_ls_number_reflns         1858
_refine_ls_number_parameters     183
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.1025
_refine_ls_wR_factor_ref         0.2087
_refine_ls_wR_factor_gt          0.2067
_refine_ls_goodness_of_fit_ref   1.230
_refine_ls_restrained_S_all      1.228
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.001

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
O1 O 0.2412(2) 0.3060(3) 0.2742(4) 0.0262(8) Uani 1 1 d . . .
C1 C 0.3212(4) 0.2661(4) 0.3196(7) 0.0307(13) Uani 1 1 d . . .
N1 N 0.3360(6) 0.2426(6) 0.4674(7) 0.085(3) Uani 1 1 d . . .
H11 H 0.2875 0.2556 0.5367 0.102 Uiso 1 1 calc R . .
H12 H 0.3945 0.2138 0.4970 0.102 Uiso 1 1 calc R . .
C2 C 0.4102(4) 0.2464(5) 0.2107(10) 0.053(2) Uani 1 1 d . . .
H2 H 0.4598 0.1970 0.2603 0.063 Uiso 1 1 calc R . .
C3 C 0.4662(7) 0.3476(8) 0.1717(18) 0.102(5) Uani 1 1 d . . .
H31 H 0.4375 0.4054 0.2337 0.122 Uiso 1 1 calc R . .
H32 H 0.5410 0.3415 0.1944 0.122 Uiso 1 1 calc R . .
C4 C 0.4488(7) 0.3648(6) 0.003(2) 0.102(5) Uani 1 1 d . . .
H41 H 0.5091 0.3991 -0.0460 0.122 Uiso 1 1 calc R . .
H42 H 0.3865 0.4077 -0.0151 0.122 Uiso 1 1 calc R . .
C5 C 0.4339(7) 0.2555(4) -0.0624(11) 0.066(3) Uani 1 1 d . . .
H51 H 0.3952 0.2568 -0.1621 0.079 Uiso 1 1 calc R . .
H52 H 0.5011 0.2207 -0.0791 0.079 Uiso 1 1 calc R . .
N2 N 0.3738(4) 0.2039(3) 0.0617(7) 0.0402(13) Uani 1 1 d . . .
C6 C 0.3839(4) 0.0916(4) 0.0545(7) 0.0336(13) Uani 1 1 d . . .
H6 H 0.4596 0.0761 0.0528 0.040 Uiso 1 1 calc R . .
C7 C 0.3376(6) 0.0428(4) -0.0926(7) 0.0422(17) Uani 1 1 d . . .
H7 H 0.3912 0.0423 -0.1767 0.051 Uiso 1 1 calc R . .
C8 C 0.2370(7) 0.0896(5) -0.1587(10) 0.065(3) Uani 1 1 d . . .
H8 H 0.2532 0.1623 -0.1902 0.078 Uiso 1 1 calc R . .
C9 C 0.1495(7) 0.0949(7) -0.0440(13) 0.079(3) Uani 1 1 d . . .
H91 H 0.0863 0.1164 -0.0981 0.119 Uiso 1 1 calc R . .
H92 H 0.1661 0.1452 0.0379 0.119 Uiso 1 1 calc R . .
H93 H 0.1389 0.0267 0.0031 0.119 Uiso 1 1 calc R . .
C10 C 0.2060(11) 0.0323(7) -0.3056(12) 0.121(6) Uani 1 1 d . . .
H101 H 0.2635 0.0333 -0.3801 0.182 Uiso 1 1 calc R . .
H102 H 0.1456 0.0659 -0.3524 0.182 Uiso 1 1 calc R . .
H103 H 0.1889 -0.0394 -0.2794 0.182 Uiso 1 1 calc R . .
N3 N 0.3218(4) -0.0631(3) -0.0373(5) 0.0342(11) Uani 1 1 d . . .
H3 H 0.3124 -0.1151 -0.1021 0.041 Uiso 1 1 calc R . .
C11 C 0.3223(5) -0.0759(5) 0.1170(6) 0.0345(14) Uani 1 1 d . . .
O2 O 0.3104(4) -0.1571(4) 0.1866(5) 0.0549(15) Uani 1 1 d . . .
C12 C 0.3382(5) 0.0306(5) 0.1889(7) 0.0378(15) Uani 1 1 d . . .
H121 H 0.2718 0.0608 0.2238 0.045 Uiso 1 1 calc R . .
H122 H 0.3864 0.0276 0.2785 0.045 Uiso 1 1 calc R . .
O3 O 0.1678(4) 0.3976(7) -0.0066(6) 0.078(2) Uani 1 1 d D . .
H3A H 0.201(7) 0.354(7) 0.057(11) 0.118 Uiso 1 1 d D . .
H3B H 0.156(9) 0.367(8) -0.098(7) 0.118 Uiso 1 1 d D . .
O4 O 0.0517(5) 0.5394(5) 0.0735(9) 0.0281(16) Uani 0.50 1 d PD . .
H4A H 0.075(9) 0.474(4) 0.054(18) 0.042 Uiso 0.50 1 d PD . .
H4B H 0.0000 0.5000 0.110(7) 0.042 Uiso 0.50 2 d SPD . .
H4C H 0.0000 0.5000 0.035(7) 0.042 Uiso 0.50 2 d SPD . .

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
O1 0.0185(16) 0.0348(19) 0.0251(18) -0.0010(17) 0.0002(15) 0.0087(14)
C1 0.026(3) 0.021(2) 0.045(3) -0.021(2) -0.017(2) 0.0060(19)
N1 0.108(6) 0.107(6) 0.040(3) -0.047(4) -0.049(4) 0.095(5)
C2 0.020(3) 0.046(4) 0.092(6) -0.045(4) -0.001(3) 0.010(2)
C3 0.042(5) 0.090(7) 0.173(14) -0.074(9) 0.047(7) -0.027(5)
C4 0.054(5) 0.034(4) 0.217(16) -0.026(7) 0.011(8) -0.003(3)
C5 0.093(6) 0.010(3) 0.094(7) -0.001(3) 0.045(5) 0.016(3)
N2 0.038(3) 0.028(2) 0.055(3) -0.019(3) 0.015(3) 0.0108(19)
C6 0.034(3) 0.030(3) 0.037(3) -0.014(3) 0.020(3) 0.004(2)
C7 0.081(5) 0.021(3) 0.024(3) -0.007(2) 0.017(3) 0.022(3)
C8 0.108(7) 0.026(3) 0.061(5) -0.026(3) -0.021(5) 0.034(4)
C9 0.065(5) 0.071(5) 0.101(8) -0.045(6) -0.040(5) 0.022(4)
C10 0.229(14) 0.056(5) 0.079(7) -0.032(5) -0.085(9) 0.076(7)
N3 0.059(3) 0.023(2) 0.021(2) -0.0098(19) 0.004(2) 0.006(2)
C11 0.039(3) 0.045(3) 0.019(3) -0.010(2) 0.009(2) -0.017(3)
O2 0.084(3) 0.060(3) 0.021(2) -0.001(2) 0.008(2) -0.053(3)
C12 0.035(3) 0.050(4) 0.028(3) -0.019(3) 0.014(3) -0.020(3)
O3 0.037(3) 0.177(7) 0.021(2) 0.017(3) 0.003(2) 0.031(3)
O4 0.032(4) 0.022(3) 0.030(4) -0.002(3) -0.001(3) -0.007(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
O1 C1 1.220(6) . ?
C1 N1 1.315(9) . ?
C1 C2 1.504(9) . ?
N1 H11 0.8800 . ?
N1 H12 0.8800 . ?
C2 N2 1.467(9) . ?
C2 C3 1.533(12) . ?
C2 H2 1.0000 . ?
C3 C4 1.482(19) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
C4 C5 1.533(11) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
C5 N2 1.476(9) . ?
C5 H51 0.9900 . ?
C5 H52 0.9900 . ?
N2 C6 1.460(6) . ?
C6 C12 1.516(8) . ?
C6 C7 1.531(9) . ?
C6 H6 1.0000 . ?
C7 N3 1.464(7) . ?
C7 C8 1.543(11) . ?
C7 H7 1.0000 . ?
C8 C9 1.501(14) . ?
C8 C10 1.515(11) . ?
C8 H8 1.0000 . ?
C9 H91 0.9800 . ?
C9 H92 0.9800 . ?
C9 H93 0.9800 . ?
C10 H101 0.9800 . ?
C10 H102 0.9800 . ?
C10 H103 0.9800 . ?
N3 C11 1.332(7) . ?
N3 H3 0.8800 . ?
C11 O2 1.217(8) . ?
C11 C12 1.524(8) . ?
C12 H121 0.9900 . ?
C12 H122 0.9900 . ?
O3 H3A 0.90(2) . ?
O3 H3B 0.90(2) . ?
O4 O4 1.683(14) 2_565 ?
O4 H4A 0.91(2) . ?
O4 H4B 0.90(2) . ?
O4 H4C 0.90(2) . ?

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
O1 C1 N1 121.9(6) . . ?
O1 C1 C2 121.6(6) . . ?
N1 C1 C2 116.5(6) . . ?
C1 N1 H11 120.0 . . ?
C1 N1 H12 120.0 . . ?
H11 N1 H12 120.0 . . ?
N2 C2 C1 110.9(5) . . ?
N2 C2 C3 106.4(8) . . ?
C1 C2 C3 110.7(5) . . ?
N2 C2 H2 109.6 . . ?
C1 C2 H2 109.6 . . ?
C3 C2 H2 109.6 . . ?
C4 C3 C2 105.6(9) . . ?
C4 C3 H31 110.6 . . ?
C2 C3 H31 110.6 . . ?
C4 C3 H32 110.6 . . ?
C2 C3 H32 110.6 . . ?
H31 C3 H32 108.7 . . ?
C3 C4 C5 103.6(10) . . ?
C3 C4 H41 111.0 . . ?
C5 C4 H41 111.0 . . ?
C3 C4 H42 111.0 . . ?
C5 C4 H42 111.0 . . ?
H41 C4 H42 109.0 . . ?
N2 C5 C4 102.8(8) . . ?
N2 C5 H51 111.2 . . ?
C4 C5 H51 111.2 . . ?
N2 C5 H52 111.2 . . ?
C4 C5 H52 111.2 . . ?
H51 C5 H52 109.1 . . ?
C6 N2 C2 112.4(6) . . ?
C6 N2 C5 111.8(4) . . ?
C2 N2 C5 106.7(5) . . ?
N2 C6 C12 116.8(5) . . ?
N2 C6 C7 114.2(5) . . ?
C12 C6 C7 104.9(4) . . ?
N2 C6 H6 106.8 . . ?
C12 C6 H6 106.8 . . ?
C7 C6 H6 106.8 . . ?
N3 C7 C6 100.1(5) . . ?
N3 C7 C8 111.6(6) . . ?
C6 C7 C8 118.0(5) . . ?
N3 C7 H7 108.9 . . ?
C6 C7 H7 108.9 . . ?
C8 C7 H7 108.9 . . ?
C9 C8 C10 111.5(9) . . ?
C9 C8 C7 114.5(7) . . ?
C10 C8 C7 109.6(6) . . ?
C9 C8 H8 107.0 . . ?
C10 C8 H8 107.0 . . ?
C7 C8 H8 107.0 . . ?
C8 C9 H91 109.5 . . ?
C8 C9 H92 109.5 . . ?
H91 C9 H92 109.5 . . ?
C8 C9 H93 109.5 . . ?
H91 C9 H93 109.5 . . ?
H92 C9 H93 109.5 . . ?
C8 C10 H101 109.5 . . ?
C8 C10 H102 109.5 . . ?
H101 C10 H102 109.5 . . ?
C8 C10 H103 109.5 . . ?
H101 C10 H103 109.5 . . ?
H102 C10 H103 109.5 . . ?
C11 N3 C7 115.9(5) . . ?
C11 N3 H3 122.1 . . ?
C7 N3 H3 122.1 . . ?
O2 C11 N3 126.3(5) . . ?
O2 C11 C12 126.9(5) . . ?
N3 C11 C12 106.8(6) . . ?
C6 C12 C11 102.6(4) . . ?
C6 C12 H121 111.3 . . ?
C11 C12 H121 111.3 . . ?
C6 C12 H122 111.3 . . ?
C11 C12 H122 111.3 . . ?
H121 C12 H122 109.2 . . ?
H3A O3 H3B 109(10) . . ?
O4 O4 H4A 73(8) 2_565 . ?
O4 O4 H4B 21(4) 2_565 . ?
H4A O4 H4B 78(8) . . ?
O4 O4 H4C 21(4) 2_565 . ?
H4A O4 H4C 70(8) . . ?
H4B O4 H4C 42(5) . . ?

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
O1 C1 C2 N2 -43.4(8) . . . . ?
N1 C1 C2 N2 139.7(7) . . . . ?
O1 C1 C2 C3 74.4(9) . . . . ?
N1 C1 C2 C3 -102.4(10) . . . . ?
N2 C2 C3 C4 6.4(9) . . . . ?
C1 C2 C3 C4 -114.1(8) . . . . ?
C2 C3 C4 C5 -27.3(10) . . . . ?
C3 C4 C5 N2 38.4(9) . . . . ?
C1 C2 N2 C6 -98.5(6) . . . . ?
C3 C2 N2 C6 141.1(6) . . . . ?
C1 C2 N2 C5 138.6(6) . . . . ?
C3 C2 N2 C5 18.2(6) . . . . ?
C4 C5 N2 C6 -158.1(7) . . . . ?
C4 C5 N2 C2 -34.9(8) . . . . ?
C2 N2 C6 C12 51.7(7) . . . . ?
C5 N2 C6 C12 171.7(6) . . . . ?
C2 N2 C6 C7 174.6(5) . . . . ?
C5 N2 C6 C7 -65.4(7) . . . . ?
N2 C6 C7 N3 -158.1(5) . . . . ?
C12 C6 C7 N3 -29.0(6) . . . . ?
N2 C6 C7 C8 -36.9(8) . . . . ?
C12 C6 C7 C8 92.3(7) . . . . ?
N3 C7 C8 C9 59.7(7) . . . . ?
C6 C7 C8 C9 -55.4(8) . . . . ?
N3 C7 C8 C10 -66.4(9) . . . . ?
C6 C7 C8 C10 178.5(8) . . . . ?
C6 C7 N3 C11 17.8(7) . . . . ?
C8 C7 N3 C11 -107.9(7) . . . . ?
C7 N3 C11 O2 179.8(6) . . . . ?
C7 N3 C11 C12 1.1(8) . . . . ?
N2 C6 C12 C11 158.0(5) . . . . ?
C7 C6 C12 C11 30.4(6) . . . . ?
O2 C11 C12 C6 161.4(7) . . . . ?
N3 C11 C12 C6 -19.9(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.04
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.060