Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2005

data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Mario Ordonez'
'Carlos Cativiela'
'Eugenio Hernandez-Fernandez'
'Janet Xahuentitla'

_publ_contact_author_name        'Prof Mario Ordonez'
_publ_contact_author_address     
;
Centro de Investigaciones Quimicas
Universidad Autonoma del Estado de Morelos
Av. Universidad 1001
Cuernavaca
Morelos
62210
MEXICO
;

_publ_contact_author_email       PALACIOS@BUZON.UAEM.MX

_publ_requested_journal          'Chemical Communications'

_publ_section_title              
;
Asymmetric alkylation of
dimethoxyphosphoryl-N-[1-(S)-alfa-methylbenzyl)acetamide enolates.
Synthesis of both stereoisomers from the same source of chirality changing the
equivalents of LDA
;

data_mario10m
_database_code_depnum_ccdc_archive 'CCDC 258161'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H26 N O4 P'
_chemical_formula_weight         375.39

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Hexagonal
_symmetry_space_group_name_H-M   P3(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'

_cell_length_a                   11.172(4)
_cell_length_b                   11.172(4)
_cell_length_c                   13.401(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     1448.4(10)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5242
_diffrn_reflns_av_R_equivalents  0.1165
_diffrn_reflns_av_sigmaI/netI    0.0771
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3277
_reflns_number_gt                3124
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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^)+(0.1622P)^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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.11(14)
_refine_ls_number_reflns         3277
_refine_ls_number_parameters     243
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0761
_refine_ls_wR_factor_ref         0.1916
_refine_ls_wR_factor_gt          0.1901
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.002

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
P1 P 1.21262(9) 0.90698(9) 0.22783(7) 0.0246(3) Uani 1 1 d . . .
O5 O 0.9916(3) 0.8762(3) 0.3878(2) 0.0299(7) Uani 1 1 d . . .
O3 O 1.2630(3) 1.0533(3) 0.2070(2) 0.0262(6) Uani 1 1 d . . .
C3 C 0.7202(4) 0.8968(4) 0.3735(3) 0.0210(8) Uani 1 1 d . . .
C11 C 0.9843(4) 0.6549(4) 0.2788(3) 0.0206(7) Uani 1 1 d . . .
H11A H 1.0433 0.6222 0.2516 0.025 Uiso 1 1 calc R . .
H11B H 1.0020 0.6685 0.3499 0.025 Uiso 1 1 calc R . .
C9 C 0.9722(4) 0.8738(3) 0.2974(2) 0.0183(7) Uani 1 1 d . . .
N1 N 0.9064(3) 0.9333(3) 0.2559(2) 0.0197(7) Uani 1 1 d . . .
C8 C 0.7108(4) 0.9026(4) 0.4768(3) 0.0239(8) Uani 1 1 d . . .
H8 H 0.7857 0.9699 0.5124 0.029 Uiso 1 1 calc R . .
C10 C 1.0241(4) 0.7969(3) 0.2297(3) 0.0186(7) Uani 1 1 d . . .
C13 C 0.8028(4) 0.4313(4) 0.2031(3) 0.0311(9) Uani 1 1 d . . .
H13 H 0.8738 0.4212 0.1758 0.037 Uiso 1 1 calc R . .
C17 C 0.7266(4) 0.5575(4) 0.3038(3) 0.0247(8) Uani 1 1 d . . .
H17 H 0.7459 0.6323 0.3448 0.030 Uiso 1 1 calc R . .
C15 C 0.5599(4) 0.3451(4) 0.2242(4) 0.0356(10) Uani 1 1 d . . .
H15 H 0.4686 0.2782 0.2120 0.043 Uiso 1 1 calc R . .
O2 O 1.2551(3) 0.8339(3) 0.1445(3) 0.0504(11) Uani 1 1 d . . .
C18 C 0.9733(4) 0.7762(4) 0.1207(3) 0.0210(7) Uani 1 1 d . . .
H18A H 0.8748 0.7367 0.1197 0.031 Uiso 1 1 calc R . .
H18B H 0.9976 0.7152 0.0874 0.031 Uiso 1 1 calc R . .
H18C H 1.0160 0.8638 0.0871 0.031 Uiso 1 1 calc R . .
C12 C 0.8347(4) 0.5450(4) 0.2626(3) 0.0226(8) Uani 1 1 d . . .
C4 C 0.6054(4) 0.7961(5) 0.3218(3) 0.0295(9) Uani 1 1 d . . .
H4 H 0.6088 0.7910 0.2527 0.035 Uiso 1 1 calc R . .
C2 C 0.8500(4) 1.0014(4) 0.3200(3) 0.0221(8) Uani 1 1 d . . .
H2 H 0.9197 1.0552 0.3707 0.027 Uiso 1 1 calc R . .
C5 C 0.4860(4) 0.7031(4) 0.3726(4) 0.0354(10) Uani 1 1 d . . .
H5 H 0.4104 0.6363 0.3372 0.042 Uiso 1 1 calc R . .
C16 C 0.5900(4) 0.4585(4) 0.2836(3) 0.0307(9) Uani 1 1 d . . .
H16 H 0.5185 0.4684 0.3101 0.037 Uiso 1 1 calc R . .
C1 C 0.8253(5) 1.1020(5) 0.2581(3) 0.0335(10) Uani 1 1 d . . .
H1A H 0.9097 1.1671 0.2256 0.050 Uiso 1 1 calc R . .
H1B H 0.7951 1.1505 0.3011 0.050 Uiso 1 1 calc R . .
H1C H 0.7556 1.0516 0.2088 0.050 Uiso 1 1 calc R . .
C14 C 0.6660(5) 0.3323(4) 0.1836(4) 0.0388(11) Uani 1 1 d . . .
H14 H 0.6463 0.2571 0.1430 0.047 Uiso 1 1 calc R . .
C7 C 0.5918(4) 0.8100(5) 0.5280(3) 0.0306(9) Uani 1 1 d . . .
H7 H 0.5878 0.8152 0.5971 0.037 Uiso 1 1 calc R . .
C6 C 0.4788(4) 0.7094(4) 0.4754(3) 0.0328(9) Uani 1 1 d . . .
H6 H 0.3990 0.6469 0.5091 0.039 Uiso 1 1 calc R . .
O1 O 1.2655(4) 0.8767(4) 0.3278(4) 0.0668(14) Uani 1 1 d . . .
C19 C 1.3855(5) 0.9754(5) 0.3796(3) 0.0343(10) Uani 1 1 d . . .
H19A H 1.4175 1.0654 0.3515 0.051 Uiso 1 1 calc R . .
H19B H 1.4566 0.9513 0.3735 0.051 Uiso 1 1 calc R . .
H19C H 1.3637 0.9760 0.4488 0.051 Uiso 1 1 calc R . .
C20 C 1.3928(4) 0.9016(5) 0.1055(4) 0.0376(10) Uani 1 1 d . . .
H20A H 1.4097 0.9831 0.0697 0.056 Uiso 1 1 calc R . .
H20B H 1.4035 0.8401 0.0611 0.056 Uiso 1 1 calc R . .
H20C H 1.4577 0.9272 0.1594 0.056 Uiso 1 1 calc R . .
H100 H 0.898(4) 0.936(4) 0.196(3) 0.004(8) Uiso 1 1 d . . .

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
P1 0.0136(5) 0.0176(5) 0.0407(6) 0.0063(4) -0.0008(4) 0.0063(4)
O5 0.0443(17) 0.0213(13) 0.0238(14) -0.0037(10) -0.0104(12) 0.0161(13)
O3 0.0177(13) 0.0161(13) 0.0403(16) 0.0010(11) -0.0018(11) 0.0051(11)
C3 0.0193(18) 0.0192(18) 0.0267(18) -0.0015(14) 0.0012(14) 0.0115(16)
C11 0.0167(17) 0.0160(18) 0.0300(18) 0.0047(14) 0.0015(14) 0.0088(14)
C9 0.0187(17) 0.0135(16) 0.0190(18) 0.0001(12) -0.0020(13) 0.0053(14)
N1 0.0197(16) 0.0237(16) 0.0172(16) 0.0010(11) 0.0023(12) 0.0119(13)
C8 0.0183(18) 0.0242(19) 0.0268(19) -0.0042(14) -0.0028(14) 0.0088(15)
C10 0.0129(17) 0.0152(17) 0.0273(18) -0.0008(14) 0.0002(13) 0.0067(14)
C13 0.025(2) 0.022(2) 0.044(2) 0.0028(17) 0.0068(16) 0.0098(17)
C17 0.0213(19) 0.0186(18) 0.0298(18) 0.0038(14) 0.0038(15) 0.0066(16)
C15 0.0198(19) 0.022(2) 0.051(3) 0.0016(18) -0.0054(17) 0.0005(17)
O2 0.0253(17) 0.0245(17) 0.099(3) 0.0015(16) 0.0261(17) 0.0106(13)
C18 0.0206(18) 0.0169(17) 0.0255(18) 0.0000(13) 0.0020(14) 0.0095(15)
C12 0.0194(18) 0.0158(18) 0.0286(19) 0.0075(14) 0.0008(14) 0.0059(15)
C4 0.025(2) 0.032(2) 0.0321(19) -0.0121(17) -0.0035(15) 0.0154(18)
C2 0.0222(19) 0.0219(18) 0.0233(16) -0.0039(14) 0.0021(14) 0.0118(16)
C5 0.020(2) 0.024(2) 0.058(3) -0.0187(19) -0.0065(18) 0.0072(17)
C16 0.0209(19) 0.028(2) 0.040(2) 0.0070(17) 0.0063(16) 0.0092(17)
C1 0.041(2) 0.031(2) 0.038(2) 0.0083(17) 0.0146(18) 0.026(2)
C14 0.034(2) 0.018(2) 0.054(3) -0.0095(17) -0.001(2) 0.0048(18)
C7 0.028(2) 0.032(2) 0.0311(19) 0.0060(17) 0.0053(16) 0.0149(18)
C6 0.0207(19) 0.021(2) 0.054(3) 0.0019(17) 0.0086(18) 0.0087(17)
O1 0.0279(18) 0.049(2) 0.093(3) 0.039(2) -0.0279(19) -0.0042(16)
C19 0.038(2) 0.040(3) 0.032(2) -0.0100(17) -0.0081(18) 0.026(2)
C20 0.022(2) 0.038(3) 0.045(2) 0.0012(18) 0.0081(17) 0.0086(18)

_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
P1 O3 1.465(3) . ?
P1 O1 1.568(4) . ?
P1 O2 1.589(4) . ?
P1 C10 1.833(4) . ?
O5 C9 1.229(4) . ?
C3 C8 1.392(5) . ?
C3 C4 1.396(6) . ?
C3 C2 1.513(5) . ?
C11 C12 1.516(5) . ?
C11 C10 1.562(5) . ?
C9 N1 1.336(5) . ?
C9 C10 1.547(5) . ?
N1 C2 1.481(5) . ?
C8 C7 1.390(6) . ?
C10 C18 1.542(5) . ?
C13 C12 1.387(6) . ?
C13 C14 1.392(6) . ?
C17 C16 1.391(6) . ?
C17 C12 1.397(6) . ?
C15 C14 1.375(7) . ?
C15 C16 1.387(7) . ?
O2 C20 1.432(5) . ?
C4 C5 1.392(6) . ?
C2 C1 1.529(6) . ?
C5 C6 1.384(7) . ?
C7 C6 1.391(6) . ?
O1 C19 1.420(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
O3 P1 O1 115.3(2) . . ?
O3 P1 O2 113.15(18) . . ?
O1 P1 O2 104.3(3) . . ?
O3 P1 C10 115.01(15) . . ?
O1 P1 C10 105.90(18) . . ?
O2 P1 C10 101.72(17) . . ?
C8 C3 C4 118.1(4) . . ?
C8 C3 C2 120.1(3) . . ?
C4 C3 C2 121.8(4) . . ?
C12 C11 C10 113.7(3) . . ?
O5 C9 N1 122.3(3) . . ?
O5 C9 C10 118.7(3) . . ?
N1 C9 C10 119.0(3) . . ?
C9 N1 C2 119.7(3) . . ?
C7 C8 C3 121.5(4) . . ?
C18 C10 C9 115.3(3) . . ?
C18 C10 C11 110.5(3) . . ?
C9 C10 C11 108.8(3) . . ?
C18 C10 P1 107.5(2) . . ?
C9 C10 P1 105.0(2) . . ?
C11 C10 P1 109.6(2) . . ?
C12 C13 C14 120.8(4) . . ?
C16 C17 C12 120.2(4) . . ?
C14 C15 C16 119.6(4) . . ?
C20 O2 P1 120.2(3) . . ?
C13 C12 C17 118.7(3) . . ?
C13 C12 C11 119.9(3) . . ?
C17 C12 C11 121.4(3) . . ?
C5 C4 C3 120.7(4) . . ?
N1 C2 C3 111.6(3) . . ?
N1 C2 C1 110.0(3) . . ?
C3 C2 C1 111.7(3) . . ?
C6 C5 C4 120.4(4) . . ?
C15 C16 C17 120.4(4) . . ?
C15 C14 C13 120.3(4) . . ?
C8 C7 C6 119.7(4) . . ?
C5 C6 C7 119.6(4) . . ?
C19 O1 P1 124.2(3) . . ?

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
O5 C9 N1 C2 -2.0(5) . . . . ?
C10 C9 N1 C2 177.0(3) . . . . ?
C4 C3 C8 C7 1.0(5) . . . . ?
C2 C3 C8 C7 178.5(4) . . . . ?
O5 C9 C10 C18 169.5(3) . . . . ?
N1 C9 C10 C18 -9.5(5) . . . . ?
O5 C9 C10 C11 44.8(4) . . . . ?
N1 C9 C10 C11 -134.2(3) . . . . ?
O5 C9 C10 P1 -72.4(4) . . . . ?
N1 C9 C10 P1 108.6(3) . . . . ?
C12 C11 C10 C18 -48.3(4) . . . . ?
C12 C11 C10 C9 79.2(4) . . . . ?
C12 C11 C10 P1 -166.6(3) . . . . ?
O3 P1 C10 C18 74.4(3) . . . . ?
O1 P1 C10 C18 -157.1(3) . . . . ?
O2 P1 C10 C18 -48.3(3) . . . . ?
O3 P1 C10 C9 -48.9(3) . . . . ?
O1 P1 C10 C9 79.7(3) . . . . ?
O2 P1 C10 C9 -171.5(2) . . . . ?
O3 P1 C10 C11 -165.5(2) . . . . ?
O1 P1 C10 C11 -37.0(3) . . . . ?
O2 P1 C10 C11 71.8(3) . . . . ?
O3 P1 O2 C20 44.3(4) . . . . ?
O1 P1 O2 C20 -81.8(4) . . . . ?
C10 P1 O2 C20 168.2(4) . . . . ?
C14 C13 C12 C17 0.7(6) . . . . ?
C14 C13 C12 C11 -177.1(4) . . . . ?
C16 C17 C12 C13 -1.0(5) . . . . ?
C16 C17 C12 C11 176.8(3) . . . . ?
C10 C11 C12 C13 112.2(4) . . . . ?
C10 C11 C12 C17 -65.6(4) . . . . ?
C8 C3 C4 C5 -0.9(6) . . . . ?
C2 C3 C4 C5 -178.4(4) . . . . ?
C9 N1 C2 C3 -74.9(4) . . . . ?
C9 N1 C2 C1 160.6(3) . . . . ?
C8 C3 C2 N1 126.4(3) . . . . ?
C4 C3 C2 N1 -56.1(5) . . . . ?
C8 C3 C2 C1 -110.0(4) . . . . ?
C4 C3 C2 C1 67.5(5) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C14 C15 C16 C17 -1.3(7) . . . . ?
C12 C17 C16 C15 1.3(6) . . . . ?
C16 C15 C14 C13 0.9(7) . . . . ?
C12 C13 C14 C15 -0.6(7) . . . . ?
C3 C8 C7 C6 -0.4(6) . . . . ?
C4 C5 C6 C7 0.3(7) . . . . ?
C8 C7 C6 C5 -0.2(6) . . . . ?
O3 P1 O1 C19 -20.7(6) . . . . ?
O2 P1 O1 C19 104.0(5) . . . . ?
C10 P1 O1 C19 -149.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.087