# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2008



data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Avinash Thadani'
_publ_contact_author_email       ATHADANI@UWINDSOR.CA

_publ_section_title              
;
Direct, facile synthesis of N-acyl-?-amino amides from
?-keto esters and ammonia
;
loop_
_publ_author_name
'Avinash Thadani'
'Tamara Milovic'
'Rukundo Ntaganda'
'Jorge Tiburcio'

# Attachment 'revised jtk77.txt'

data_jtk77
_database_code_depnum_ccdc_archive 'CCDC 688365'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 N2 O2'
_chemical_formula_sum            'C15 H14 N2 O2'
_chemical_formula_weight         254.28

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   C2/c

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

_cell_length_a                   18.101(4)
_cell_length_b                   7.1667(14)
_cell_length_c                   20.677(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.16(3)
_cell_angle_gamma                90.00
_cell_volume                     2631.6(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      2
_cell_measurement_theta_max      7

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9786
_exptl_absorpt_correction_T_max  0.9984
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
(Sheldrick, 2002)
;

_diffrn_ambient_temperature      293(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  'Nonius Kappa CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7631
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_sigmaI/netI    0.0532
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.037
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2245
_reflns_number_gt                1649
_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    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_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^)+(0.0511P)^2^+0.7525P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2245
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1161
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
O1 O 0.22926(6) -0.01046(18) 0.44908(7) 0.0565(4) Uani 1 1 d . . .
N1 N 0.12201(7) -0.01089(18) 0.48979(7) 0.0388(4) Uani 1 1 d . . .
H1A H 0.0800 -0.0674 0.4893 0.047 Uiso 1 1 calc R . .
C1 C 0.05643(9) -0.2335(3) 0.37526(9) 0.0521(5) Uani 1 1 d . . .
H1B H 0.0252 -0.1338 0.3804 0.063 Uiso 1 1 calc R . .
O2 O 0.01392(5) 0.24669(16) 0.49937(6) 0.0449(3) Uani 1 1 d . . .
N2 N 0.10330(7) 0.46804(19) 0.52336(8) 0.0491(4) Uani 1 1 d . . .
H2A H 0.0711 0.5574 0.5154 0.059 Uiso 1 1 calc R . .
H2B H 0.1504 0.4927 0.5356 0.059 Uiso 1 1 calc R . .
C2 C 0.02715(10) -0.3865(3) 0.33928(11) 0.0707(7) Uani 1 1 d . . .
H2C H -0.0237 -0.3897 0.3201 0.085 Uiso 1 1 calc R . .
C3 C 0.07229(11) -0.5339(3) 0.33153(12) 0.0743(7) Uani 1 1 d . . .
H3A H 0.0518 -0.6387 0.3082 0.089 Uiso 1 1 calc R . .
C4 C 0.14766(11) -0.5279(3) 0.35806(11) 0.0661(6) Uani 1 1 d . . .
H4A H 0.1785 -0.6278 0.3521 0.079 Uiso 1 1 calc R . .
C5 C 0.17786(9) -0.3745(3) 0.39344(9) 0.0496(5) Uani 1 1 d . . .
H5A H 0.2293 -0.3700 0.4105 0.060 Uiso 1 1 calc R . .
C6 C 0.13247(8) -0.2266(2) 0.40399(8) 0.0380(4) Uani 1 1 d . . .
C7 C 0.16578(8) -0.0721(2) 0.44852(8) 0.0377(4) Uani 1 1 d . . .
C8 C 0.14097(8) 0.1437(2) 0.53483(8) 0.0375(4) Uani 1 1 d . . .
H8A H 0.1896 0.1953 0.5296 0.045 Uiso 1 1 calc R . .
C9 C 0.08046(8) 0.2937(2) 0.51674(8) 0.0359(4) Uani 1 1 d . . .
C10 C 0.14539(8) 0.0910(2) 0.60705(8) 0.0398(4) Uani 1 1 d . . .
C11 C 0.11976(10) -0.0782(3) 0.62598(10) 0.0540(5) Uani 1 1 d . . .
H11A H 0.0995 -0.1655 0.5941 0.065 Uiso 1 1 calc R . .
C12 C 0.12404(12) -0.1185(4) 0.69206(12) 0.0735(7) Uani 1 1 d . . .
H12A H 0.1072 -0.2336 0.7042 0.088 Uiso 1 1 calc R . .
C13 C 0.15245(13) 0.0074(4) 0.73953(12) 0.0768(7) Uani 1 1 d . . .
H13A H 0.1547 -0.0211 0.7837 0.092 Uiso 1 1 calc R . .
C14 C 0.17776(12) 0.1765(4) 0.72197(11) 0.0724(7) Uani 1 1 d . . .
H14A H 0.1972 0.2630 0.7543 0.087 Uiso 1 1 calc R . .
C15 C 0.17440(10) 0.2187(3) 0.65611(10) 0.0557(5) Uani 1 1 d . . .
H15A H 0.1917 0.3338 0.6445 0.067 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
O1 0.0358(6) 0.0663(9) 0.0722(10) -0.0143(7) 0.0227(6) -0.0099(6)
N1 0.0309(6) 0.0358(9) 0.0524(9) -0.0078(6) 0.0147(6) -0.0041(5)
C1 0.0366(9) 0.0668(13) 0.0521(12) -0.0111(10) 0.0063(8) 0.0125(9)
O2 0.0302(6) 0.0373(7) 0.0659(9) 0.0000(6) 0.0062(5) -0.0022(5)
N2 0.0333(7) 0.0311(9) 0.0810(12) 0.0018(7) 0.0063(7) -0.0018(6)
C2 0.0387(10) 0.0971(18) 0.0727(15) -0.0343(13) 0.0017(9) 0.0005(11)
C3 0.0597(12) 0.0842(17) 0.0778(17) -0.0419(13) 0.0103(11) -0.0055(12)
C4 0.0572(12) 0.0656(15) 0.0762(16) -0.0252(12) 0.0145(10) 0.0119(10)
C5 0.0371(9) 0.0576(13) 0.0542(12) -0.0087(9) 0.0090(8) 0.0082(8)
C6 0.0334(8) 0.0446(11) 0.0376(10) -0.0006(8) 0.0107(7) 0.0050(7)
C7 0.0303(8) 0.0395(10) 0.0442(10) 0.0033(8) 0.0100(7) 0.0044(7)
C8 0.0263(7) 0.0338(10) 0.0533(11) -0.0039(8) 0.0101(7) -0.0010(6)
C9 0.0311(8) 0.0357(10) 0.0426(10) 0.0002(7) 0.0111(6) -0.0013(7)
C10 0.0282(7) 0.0397(11) 0.0507(11) -0.0025(8) 0.0060(7) 0.0075(7)
C11 0.0540(10) 0.0510(12) 0.0569(13) 0.0013(10) 0.0102(9) -0.0021(9)
C12 0.0778(14) 0.0773(17) 0.0655(17) 0.0182(13) 0.0144(11) -0.0031(12)
C13 0.0804(15) 0.099(2) 0.0500(15) 0.0088(14) 0.0114(12) 0.0134(14)
C14 0.0757(14) 0.0837(18) 0.0519(14) -0.0153(12) -0.0026(10) 0.0125(13)
C15 0.0516(10) 0.0520(13) 0.0602(14) -0.0074(10) 0.0024(9) 0.0035(9)

_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 C7 1.2292(18) . ?
N1 C7 1.345(2) . ?
N1 C8 1.445(2) . ?
C1 C2 1.373(3) . ?
C1 C6 1.390(2) . ?
O2 C9 1.2351(17) . ?
N2 C9 1.315(2) . ?
C2 C3 1.364(3) . ?
C3 C4 1.369(3) . ?
C4 C5 1.374(3) . ?
C5 C6 1.384(2) . ?
C6 C7 1.491(2) . ?
C8 C10 1.527(2) . ?
C8 C9 1.529(2) . ?
C10 C11 1.382(3) . ?
C10 C15 1.392(2) . ?
C11 C12 1.384(3) . ?
C12 C13 1.359(3) . ?
C13 C14 1.369(3) . ?
C14 C15 1.385(3) . ?

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
C7 N1 C8 124.27(13) . . ?
C2 C1 C6 120.42(17) . . ?
C3 C2 C1 120.35(18) . . ?
C2 C3 C4 120.1(2) . . ?
C3 C4 C5 120.08(19) . . ?
C4 C5 C6 120.64(16) . . ?
C5 C6 C1 118.31(16) . . ?
C5 C6 C7 118.99(14) . . ?
C1 C6 C7 122.61(14) . . ?
O1 C7 N1 122.76(16) . . ?
O1 C7 C6 122.58(14) . . ?
N1 C7 C6 114.62(13) . . ?
N1 C8 C10 113.66(13) . . ?
N1 C8 C9 108.17(13) . . ?
C10 C8 C9 108.21(12) . . ?
O2 C9 N2 123.96(14) . . ?
O2 C9 C8 119.45(14) . . ?
N2 C9 C8 116.54(13) . . ?
C11 C10 C15 118.09(18) . . ?
C11 C10 C8 122.48(16) . . ?
C15 C10 C8 119.41(16) . . ?
C10 C11 C12 120.3(2) . . ?
C13 C12 C11 121.0(2) . . ?
C12 C13 C14 119.7(2) . . ?
C13 C14 C15 120.1(2) . . ?
C14 C15 C10 120.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.035