Electronic Supplementary Material for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2005

data_global

_journal_coden_Cambridge         177
_journal_volume                  ?
_journal_year                    ?
_journal_page_first              ?

_publ_requested_journal          'Chemical Communications'

_publ_contact_author_name        'Karl Anker Jorgensen'
_publ_contact_author_address     
;
Department of Chemistry
Aarhus University
Aarhus C
DK 8000
DENMARK
;

_publ_contact_author_email       KAJ@CHEM.AU.DK

_publ_section_title              
;
Catalytic asymmetric addition of beta-keto
phosphonates to an activated imine - formation of optically active
functionalized phosphonate alpha-amino acid derivatives
;
#==============================================================================

# 3. TITLE AND AUTHOR LIST

loop_
_publ_author_name
'Anne Kjaersgaard'
'Karl Anker Joergensen'

_publ_author_address             
;     Department of Chemistry
Aarhus University
Langelandsgade 140
DK-8000 \%Arhus C
Denmark
;
_publ_section_references         
;

Allen,F.H., Davies,J.E., Galloy,J.J., Johnson,O.,
Kennard,O., Macrae,C.F., Mitchell,E.M., Mitchell,G.F.,
Smith,J.M., Watson,D.G. (1991). J. Chem. Inf. Comp. Sci.
31, 187-204.

Altomare,A., Cascarano,G., Giacovazzo,C., Guagliardi,A.,
Moliterni,.A,G,G., Burla,M.C., Polidori,G., Camalli,M.
& Spagna,R. (1997). SIR97. University of Bari, Italy.

Becker,P.J. & Coppens, P. (1974). Acta Cryst. A30, 129-153.

Burnett,M.N. & Johnson,C.K. (1996). ORTEP-III. Report ORNL-6895.
Oak Ridge National Laboratory, Tennessee, USA.

Busing,W.R., Martin,K.O. & Levy,H.A. (1962). ORFLS. Report
ORNL-TM-305. Oak Ridge National Laboratory, Tennessee, USA.

Hazell,A. (1995). KRYSTAL, An integrated system of
crystallographic programs. Aarhus University, Denmark.

Rogers,D. (1981). Acta Cryst. A37, 734-741.

Siemens (1995) SMART, SAINT and XPREP Area-Detector Control and
Integration Software. Siemens Analytical X-ray Instruments Inc.
Madison, Wisconsin, USA.

;

#===================================
data_cpd_3e
_database_code_depnum_ccdc_archive 'CCDC 253695'
#===================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
3-(Diethoxy-phosphoryl)-3-methyl-4-oxo-2-(toluene-4-sulfonylamino)-
pentanoic acid ethyl ester
;
_chemical_formula_sum            'C19 H30 N O8 P S'
_chemical_formula_moiety         'C19 H30 N O8 P S'
_chemical_formula_weight         463.48

#===================================
# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   7.997(2)
_cell_length_b                   12.221(2)
_cell_length_c                   11.812(2)
_cell_angle_alpha                90.000
_cell_angle_beta                 100.647(4)
_cell_angle_gamma                90.000
_cell_volume                     1134.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    7926
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      32.21
_exptl_crystal_description       box
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             492
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, 1996      '
_exptl_absorpt_correction_T_min  0.819
_exptl_absorpt_correction_T_max  0.960

#===================================

# 7. EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'

_diffrn_reflns_number            32788
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         34.40
_diffrn_reflns_reduction_process 32788
_reflns_number_total             9477
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_theta_full        30.51
_reflns_number_gt                7921
_reflns_threshold_expression     I>0
_computing_structure_solution    
;
SIR97 (Altomare et al., 1997 ), KRYSTAL
;
_computing_structure_refinement  'modified ORFLS(1962), KRYSTAL'
_computing_molecular_graphics    
;
ORTEP-III (Burnett & Johnson,  1996), KRYSTAL
;
_computing_publication_material  KRYSTAL
_atom_type_scat_source           IntTabIV

#===================================

# 8. REFINEMENT DATA

_refine_special_details          
;
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
w= 1/{[\s~cs~(F^2^)+B+(1+A)F^2^]^1/2^- |F|}^2^
where A = 0.05 and B = 0.4
;
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details 
; Least squares refinement included a factor according to Rogers (1981),
refined against all 7921 non negative intensities, including 3798
Bijvoet pairs.
;
_refine_ls_abs_structure_Rogers  0.84(8)
_refine_ls_number_reflns         7921
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_gt           0.033
_refine_ls_wR_factor_ref         0.048
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_shift/su_max          0.0011
_refine_ls_shift/su_mean         0.0001
_refine_diff_density_max         1.2(1)
_refine_diff_density_min         -0.6(1)

#==========================================

# 9. ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
S1 0.39068(3) 0.77492(3) 0.64561(2) 0.0136(1) Uij 1.0
P2 0.10635(4) 0.47373(3) 0.55765(3) 0.0141(1) Uij 1.0
O1 0.03320(14) 0.49168(10) 0.82630(9) 0.0246(5) Uij 1.0
O2 0.17819(14) 0.73475(10) 0.88802(9) 0.0252(5) Uij 1.0
O3 -0.07816(15) 0.76106(14) 0.77758(12) 0.0409(7) Uij 1.0
O4 0.00262(12) 0.37430(9) 0.52942(9) 0.0210(4) Uij 1.0
O5 0.28732(11) 0.45069(8) 0.63086(10) 0.0206(4) Uij 1.0
O6 0.13419(15) 0.54312(9) 0.45160(9) 0.0245(5) Uij 1.0
O7 0.50227(12) 0.68678(8) 0.69054(9) 0.0198(4) Uij 1.0
O8 0.41177(13) 0.82894(9) 0.54068(8) 0.0204(4) Uij 1.0
N1 0.19705(12) 0.73002(9) 0.62229(9) 0.0136(4) Uij 1.0
C1 0.0041(1) 0.5730(1) 0.6396(1) 0.0118(4) Uij 1.0
C2 0.1364(1) 0.6563(1) 0.7030(1) 0.0122(5) Uij 1.0
C3 0.0609(2) 0.7219(1) 0.7925(1) 0.0166(5) Uij 1.0
C4 -0.0595(2) 0.5049(1) 0.7335(1) 0.0159(5) Uij 1.0
C5 -0.2358(2) 0.4572(1) 0.7070(1) 0.0212(6) Uij 1.0
C6 -0.1435(1) 0.6261(1) 0.5545(1) 0.0152(5) Uij 1.0
C7 0.1294(2) 0.7970(2) 0.9814(1) 0.0321(8) Uij 1.0
C8 0.0623(4) 0.7213(2) 1.0611(2) 0.0619(17) Uij 1.0
C9 0.3503(2) 0.3412(1) 0.6640(1) 0.0196(5) Uij 1.0
C10 0.3881(2) 0.3320(2) 0.7932(1) 0.0288(7) Uij 1.0
C11 0.2488(2) 0.5094(1) 0.3743(2) 0.0310(8) Uij 1.0
C12 0.3612(3) 0.6009(2) 0.3584(2) 0.0498(13) Uij 1.0
C13 0.4068(1) 0.8759(1) 0.7541(1) 0.0141(5) Uij 1.0
C14 0.2754(2) 0.9515(1) 0.7514(1) 0.0182(5) Uij 1.0
C15 0.2869(2) 1.0290(1) 0.8385(1) 0.0220(6) Uij 1.0
C16 0.4287(2) 1.0327(1) 0.9281(1) 0.0222(6) Uij 1.0
C17 0.5618(2) 0.9593(1) 0.9255(1) 0.0204(6) Uij 1.0
C18 0.5513(2) 0.8801(1) 0.8397(1) 0.0169(5) Uij 1.0
C19 0.4361(2) 1.1127(1) 1.0263(1) 0.0314(8) Uij 1.0
H1n 0.1268 0.7658 0.5800 0.016 Uiso 1.0
H2 0.2313 0.6161 0.7427 0.015 Uiso 1.0
H5a -0.2750 0.4154 0.7645 0.025 Uiso 1.0
H5b -0.2406 0.4110 0.6415 0.025 Uiso 1.0
H5c -0.3130 0.5164 0.6876 0.025 Uiso 1.0
H6a -0.1966 0.6774 0.5969 0.018 Uiso 1.0
H6b -0.2233 0.5717 0.5223 0.018 Uiso 1.0
H6c -0.1009 0.6621 0.4945 0.018 Uiso 1.0
H7a 0.0437 0.8482 0.9506 0.038 Uiso 1.0
H7b 0.2259 0.8347 1.0220 0.038 Uiso 1.0
H8a 0.0304 0.7617 1.1225 0.074 Uiso 1.0
H8b 0.1481 0.6697 1.0920 0.074 Uiso 1.0
H8c -0.0341 0.6833 1.0206 0.074 Uiso 1.0
H9a 0.4515 0.3282 0.6346 0.023 Uiso 1.0
H9b 0.2667 0.2888 0.6331 0.023 Uiso 1.0
H10a 0.4292 0.2607 0.8149 0.035 Uiso 1.0
H10b 0.2870 0.3452 0.8227 0.035 Uiso 1.0
H10c 0.4719 0.3846 0.8242 0.035 Uiso 1.0
H11a 0.1835 0.4887 0.3018 0.037 Uiso 1.0
H11b 0.3153 0.4489 0.4069 0.037 Uiso 1.0
H12a 0.4355 0.5790 0.3080 0.059 Uiso 1.0
H12b 0.4265 0.6213 0.4305 0.059 Uiso 1.0
H12c 0.2946 0.6612 0.3254 0.059 Uiso 1.0
H14 0.1790 0.9498 0.6908 0.022 Uiso 1.0
H15 0.1974 1.0804 0.8371 0.026 Uiso 1.0
H17 0.6613 0.9635 0.9833 0.025 Uiso 1.0
H18 0.6417 0.8295 0.8399 0.020 Uiso 1.0
H19a 0.3738 1.1766 0.9994 0.037 Uiso 0.5
H19b 0.5512 1.1314 1.0554 0.037 Uiso 0.5
H19c 0.3878 1.0802 1.0860 0.037 Uiso 0.5
H19d 0.5013 1.0821 1.0943 0.037 Uiso 0.5
H19e 0.3240 1.1273 1.0384 0.037 Uiso 0.5
H19f 0.4874 1.1786 1.0077 0.037 Uiso 0.5

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0108(1) 0.0140(1) 0.0167(1) -0.0016(1) 0.0041(1) -0.0018(1)
P2 0.0122(1) 0.0121(1) 0.0182(1) 0.0003(1) 0.0031(1) -0.0031(1)
O1 0.0247(5) 0.0276(5) 0.0207(4) -0.0050(4) 0.0020(4) 0.0060(4)
O2 0.0248(5) 0.0327(5) 0.0174(4) 0.0009(4) 0.0025(4) -0.0080(4)
O3 0.0202(5) 0.0583(9) 0.0418(7) 0.0137(5) -0.0002(5) -0.0302(7)
O4 0.0156(4) 0.0156(4) 0.0305(5) -0.0006(3) 0.0010(3) -0.0097(4)
O5 0.0125(4) 0.0128(4) 0.0350(5) 0.0010(3) 0.0007(3) -0.0033(4)
O6 0.0304(5) 0.0243(5) 0.0228(5) 0.0077(4) 0.0152(4) 0.0021(4)
O7 0.0116(4) 0.0181(4) 0.0298(5) 0.0024(3) 0.0040(3) -0.0035(4)
O8 0.0210(4) 0.0249(5) 0.0170(4) -0.0079(4) 0.0083(3) -0.0013(3)
N1 0.0104(4) 0.0132(4) 0.0166(4) -0.0017(3) 0.0007(3) 0.0016(3)
C1 0.0099(4) 0.0106(4) 0.0150(4) -0.0005(3) 0.0023(3) -0.0007(3)
C2 0.0106(4) 0.0118(4) 0.0143(4) -0.0008(3) 0.0025(3) -0.0007(3)
C3 0.0165(5) 0.0156(5) 0.0181(5) -0.0021(4) 0.0049(4) -0.0036(4)
C4 0.0155(5) 0.0132(4) 0.0199(5) -0.0007(4) 0.0056(4) 0.0006(4)
C5 0.0157(5) 0.0213(6) 0.0280(6) -0.0043(4) 0.0077(4) 0.0025(5)
C6 0.0112(5) 0.0144(5) 0.0188(5) 0.0002(4) -0.0001(4) 0.0003(4)
C7 0.0375(8) 0.0375(9) 0.0229(6) -0.0077(6) 0.0097(6) -0.0132(6)
C8 0.1019(21) 0.0507(13) 0.0488(12) -0.0304(14) 0.0547(14) -0.0177(10)
C9 0.0188(5) 0.0148(5) 0.0241(6) 0.0048(4) 0.0007(4) -0.0032(4)
C10 0.0284(7) 0.0336(8) 0.0250(6) 0.0023(6) 0.0069(5) 0.0027(6)
C11 0.0389(8) 0.0231(6) 0.0377(8) 0.0043(6) 0.0248(7) 0.0002(6)
C12 0.0576(13) 0.0336(9) 0.0711(15) -0.0131(9) 0.0455(12) -0.0217(10)
C13 0.0134(5) 0.0137(5) 0.0151(4) -0.0021(4) 0.0025(4) -0.0010(4)
C14 0.0161(5) 0.0166(5) 0.0215(5) 0.0010(4) 0.0021(4) -0.0032(4)
C15 0.0224(6) 0.0180(5) 0.0259(6) 0.0006(5) 0.0050(5) -0.0055(5)
C16 0.0277(6) 0.0192(5) 0.0204(5) -0.0073(5) 0.0065(5) -0.0043(5)
C17 0.0223(6) 0.0214(6) 0.0161(5) -0.0067(4) -0.0004(4) 0.0004(4)
C18 0.0149(5) 0.0174(5) 0.0181(5) -0.0020(4) 0.0020(4) 0.0027(4)
C19 0.0422(9) 0.0284(7) 0.0244(6) -0.0083(6) 0.0081(6) -0.0116(6)

#=================================

# 10. MOLECULAR GEOMETRY

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O7 1.436(1)
S1 O8 1.441(1)
S1 N1 1.618(1)
S1 C13 1.767(1)
P2 O4 1.474(1)
P2 O6 1.562(1)
P2 O5 1.568(1)
P2 C1 1.836(1)
O1 C4 1.215(2)
O2 C3 1.336(2)
O2 C7 1.451(2)
O3 C3 1.194(2)
O5 C9 1.458(2)
O6 C11 1.467(2)
N1 C2 1.458(2)
C1 C4 1.546(2)
C1 C6 1.544(2)
C1 C2 1.558(2)
C2 C3 1.536(2)
C4 C5 1.504(2)
C7 C8 1.488(3)
C9 C10 1.504(2)
C11 C12 1.468(3)
C13 C18 1.389(2)
C13 C14 1.395(2)
C14 C15 1.389(2)
C15 C16 1.402(2)
C16 C17 1.396(2)
C16 C19 1.510(2)
C17 C18 1.392(2)
N1 H1n 0.81
C2 H2 0.95
C5 H5b 0.95
C5 H5a 0.95
C5 H5c 0.95
C6 H6c 0.95
C6 H6b 0.95
C6 H6a 0.95
C7 H7a 0.95
C7 H7b 0.95
C8 H8c 0.95
C8 H8b 0.95
C8 H8a 0.95
C9 H9a 0.95
C9 H9b 0.95
C10 H10a 0.95
C10 H10c 0.95
C10 H10b 0.95
C11 H11a 0.95
C11 H11b 0.95
C12 H12a 0.95
C12 H12c 0.95
C12 H12b 0.95
C14 H14 0.95
C15 H15 0.95
C17 H17 0.95
C18 H18 0.95
C19 H19b 0.95
C19 H19f 0.95
C19 H19d 0.95
C19 H19a 0.95
C19 H19c 0.95
C19 H19e 0.95

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O8 S1 O7 119.85(6)
N1 S1 O7 108.56(6)
C13 S1 O7 107.39(6)
N1 S1 O8 105.63(6)
C13 S1 O8 107.42(6)
C13 S1 N1 107.44(5)
O6 P2 O4 115.06(7)
O5 P2 O4 113.58(6)
C1 P2 O4 112.16(6)
O5 P2 O6 106.61(6)
C1 P2 O6 101.96(6)
C1 P2 O5 106.49(6)
C7 O2 C3 117.3(1)
P2 O5 C9 123.43(8)
P2 O6 C11 123.0(1)
S1 N1 C2 121.45(8)
C6 C1 C4 112.3(1)
C2 C1 C4 106.90(9)
P2 C1 C4 105.06(8)
C2 C1 C6 114.11(9)
P2 C1 C6 107.20(8)
P2 C1 C2 110.89(8)
C3 C2 N1 110.40(9)
C1 C2 N1 111.55(9)
C1 C2 C3 110.73(9)
O2 C3 O3 124.5(1)
C2 C3 O3 125.5(1)
C2 C3 O2 109.8(1)
C5 C4 O1 121.9(1)
C1 C4 O1 119.5(1)
C1 C4 C5 118.6(1)
C8 C7 O2 109.5(2)
C10 C9 O5 109.6(1)
C12 C11 O6 109.5(1)
C14 C13 C18 121.0(1)
S1 C13 C18 119.54(9)
S1 C13 C14 119.50(9)
C13 C14 C15 119.2(1)
C16 C15 C14 121.0(1)
C15 C16 C17 118.4(1)
C19 C16 C17 120.7(1)
C19 C16 C15 120.8(1)
C16 C17 C18 121.3(1)
C13 C18 C17 119.0(1)
C2 N1 H1n 117.5
S1 N1 H1n 117.1
N1 C2 H2 108.0
C3 C2 H2 108.0
C1 C2 H2 108.0
H5a C5 H5b 107.1
H5c C5 H5b 109.1
C4 C5 H5b 107.1
H5c C5 H5a 107.2
C4 C5 H5a 118.7
C4 C5 H5c 107.3
H6b C6 H6c 109.5
H6a C6 H6c 110.0
C1 C6 H6c 110.1
H6a C6 H6b 109.9
C1 C6 H6b 110.0
C1 C6 H6a 107.2
H7b C7 H7a 109.5
O2 C7 H7a 109.3
C8 C7 H7a 109.5
O2 C7 H7b 109.3
C8 C7 H7b 109.7
H8b C8 H8c 109.2
H8a C8 H8c 109.4
C7 C8 H8c 109.8
H8a C8 H8b 109.1
C7 C8 H8b 109.5
C7 C8 H8a 109.8
H9b C9 H9a 109.5
O5 C9 H9a 109.3
C10 C9 H9a 109.5
O5 C9 H9b 109.4
C10 C9 H9b 109.5
H10c C10 H10a 109.3
H10b C10 H10a 109.4
C9 C10 H10a 109.7
H10b C10 H10c 109.3
C9 C10 H10c 109.6
C9 C10 H10b 109.5
H11b C11 H11a 109.4
O6 C11 H11a 109.4
C12 C11 H11a 109.5
O6 C11 H11b 109.5
C12 C11 H11b 109.6
H12c C12 H12a 109.2
H12b C12 H12a 109.3
C11 C12 H12a 109.5
H12b C12 H12c 109.8
C11 C12 H12c 109.5
C11 C12 H12b 109.6
C15 C14 H14 120.5
C13 C14 H14 120.3
C14 C15 H15 119.5
C16 C15 H15 119.6
C18 C17 H17 119.3
C16 C17 H17 119.4
C17 C18 H18 120.5
C13 C18 H18 120.5
H19f C19 H19b 56.4
H19d C19 H19b 56.3
H19a C19 H19b 109.7
H19c C19 H19b 109.4
H19e C19 H19b 141.2
C16 C19 H19b 109.4
H19d C19 H19f 109.7
H19e C19 H19f 109.7
C16 C19 H19f 109.2
H19e C19 H19d 109.4
C16 C19 H19d 109.4
H19c C19 H19a 109.3
C16 C19 H19a 109.4
C16 C19 H19c 109.6
C16 C19 H19e 109.4