# Supplementary Material (ESI) for Chemical Science
# This journal is (c) The Royal Society of Chemistry 2010
data_global

_journal_coden_Cambridge         1475

loop_
_publ_author_name
'Stoll, Armin'
'Blakey, Simon'

_publ_contact_author_name        'Blakey, Simon'
_publ_contact_author_email       sblakey@emory.edu

_publ_section_title              
;
Rhodium Catalyzed Allene Amidation: A Facile Entry into 2
Amidoallylcations for Unusual [3+3] Annulation Reactions
;

# Attachment '- AST320S.txt'

data_ast320s
_database_code_depnum_ccdc_archive 'CCDC 750091'
#TrackingRef '- AST320S.txt'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H22 N2 O5 S'
_chemical_formula_sum            'C19 H22 N2 O5 S'
_chemical_formula_weight         390.45

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   6.9683(13)
_cell_length_b                   21.374(4)
_cell_length_c                   12.566(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.0910(10)
_cell_angle_gamma                90.00
_cell_volume                     1871.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    172(2)
_cell_measurement_reflns_used    3367
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      25.25

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9618
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      172(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            26054
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         29.46
_reflns_number_total             5159
_reflns_number_gt                3682
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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^)+(0.0600P)^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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5159
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1252
_refine_ls_wR_factor_gt          0.1119
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.002
_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
C1 C 0.0314(2) 0.65220(8) -0.00023(13) 0.0192(3) Uani 1 1 d . . .
C2 C -0.1016(2) 0.66906(8) 0.09213(13) 0.0173(3) Uani 1 1 d . . .
H2A H -0.1542 0.6285 0.1183 0.021 Uiso 1 1 calc R . .
C3 C 0.1643(2) 0.64886(7) 0.22430(12) 0.0168(3) Uani 1 1 d . . .
H3A H 0.2944 0.6686 0.2263 0.020 Uiso 1 1 calc R . .
C4 C 0.1075(3) 0.70868(8) -0.06120(14) 0.0230(4) Uani 1 1 d . . .
H4A H 0.1912 0.6933 -0.1183 0.028 Uiso 1 1 calc R . .
H4B H -0.0027 0.7303 -0.0959 0.028 Uiso 1 1 calc R . .
C5 C 0.2190(3) 0.75598(8) 0.00463(15) 0.0242(4) Uani 1 1 d . . .
H5A H 0.3167 0.7340 0.0490 0.029 Uiso 1 1 calc R . .
H5B H 0.2867 0.7850 -0.0433 0.029 Uiso 1 1 calc R . .
C6 C -0.0636(3) 0.60496(9) -0.07469(15) 0.0291(4) Uani 1 1 d . . .
H6A H 0.0236 0.5950 -0.1326 0.044 Uiso 1 1 calc R . .
H6B H -0.1827 0.6227 -0.1044 0.044 Uiso 1 1 calc R . .
H6C H -0.0928 0.5667 -0.0351 0.044 Uiso 1 1 calc R . .
C7 C -0.2756(2) 0.70937(9) 0.06294(14) 0.0235(4) Uani 1 1 d . . .
H7A H -0.2323 0.7518 0.0429 0.028 Uiso 1 1 calc R . .
H7B H -0.3444 0.6909 0.0009 0.028 Uiso 1 1 calc R . .
C8 C 0.3085(2) 0.55012(7) 0.17015(13) 0.0186(3) Uani 1 1 d . . .
C9 C 0.2669(3) 0.50335(8) 0.24309(14) 0.0260(4) Uani 1 1 d . . .
H9A H 0.1458 0.5026 0.2765 0.031 Uiso 1 1 calc R . .
C10 C 0.4033(3) 0.45774(9) 0.26696(16) 0.0319(5) Uani 1 1 d . . .
H10A H 0.3758 0.4262 0.3177 0.038 Uiso 1 1 calc R . .
C11 C 0.5775(3) 0.45790(9) 0.21769(16) 0.0322(5) Uani 1 1 d . . .
H11A H 0.6698 0.4264 0.2339 0.039 Uiso 1 1 calc R . .
C12 C 0.6174(3) 0.50388(10) 0.14477(17) 0.0358(5) Uani 1 1 d . . .
H12A H 0.7378 0.5039 0.1105 0.043 Uiso 1 1 calc R . .
C13 C 0.4843(3) 0.55035(8) 0.12048(15) 0.0271(4) Uani 1 1 d . . .
H13A H 0.5136 0.5820 0.0703 0.033 Uiso 1 1 calc R . .
C14 C 0.1118(3) 0.62733(8) 0.33436(13) 0.0204(4) Uani 1 1 d . . .
C15 C 0.2483(3) 0.62973(9) 0.41549(15) 0.0344(5) Uani 1 1 d . . .
H15A H 0.3733 0.6451 0.4017 0.041 Uiso 1 1 calc R . .
C16 C 0.2034(4) 0.60981(11) 0.51697(17) 0.0486(6) Uani 1 1 d . . .
H16A H 0.2972 0.6120 0.5727 0.058 Uiso 1 1 calc R . .
C17 C 0.0231(4) 0.58688(10) 0.53729(17) 0.0488(6) Uani 1 1 d . . .
H17A H -0.0072 0.5733 0.6069 0.059 Uiso 1 1 calc R . .
C18 C -0.1133(3) 0.58368(10) 0.45683(17) 0.0398(5) Uani 1 1 d . . .
H18A H -0.2369 0.5672 0.4710 0.048 Uiso 1 1 calc R . .
C19 C -0.0714(3) 0.60426(9) 0.35541(15) 0.0286(4) Uani 1 1 d . . .
H19A H -0.1666 0.6027 0.3004 0.034 Uiso 1 1 calc R . .
N1 N 0.1608(2) 0.59582(6) 0.14742(10) 0.0172(3) Uani 1 1 d . . .
N2 N 0.01982(19) 0.69418(6) 0.18090(10) 0.0161(3) Uani 1 1 d . . .
O1 O 0.20558(16) 0.62489(5) 0.04638(9) 0.0198(3) Uani 1 1 d . . .
O2 O 0.09149(17) 0.79199(5) 0.07379(10) 0.0227(3) Uani 1 1 d . . .
O3 O 0.23098(19) 0.77606(6) 0.25414(11) 0.0291(3) Uani 1 1 d . . .
O4 O -0.10802(18) 0.80050(6) 0.22084(10) 0.0266(3) Uani 1 1 d . . .
O5 O -0.40171(17) 0.71356(6) 0.14995(11) 0.0305(3) Uani 1 1 d . . .
H5C H -0.3570 0.7389 0.1951 0.046 Uiso 1 1 calc R . .
S1 S 0.06177(6) 0.768255(19) 0.19051(3) 0.01914(12) Uani 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
C1 0.0196(8) 0.0215(8) 0.0163(8) 0.0013(6) -0.0030(6) 0.0051(7)
C2 0.0156(8) 0.0194(8) 0.0167(8) -0.0008(6) -0.0020(6) 0.0002(6)
C3 0.0165(8) 0.0164(8) 0.0173(8) 0.0005(6) -0.0021(6) 0.0009(6)
C4 0.0237(9) 0.0280(9) 0.0175(8) 0.0048(7) 0.0034(7) 0.0082(7)
C5 0.0203(9) 0.0260(9) 0.0267(9) 0.0071(7) 0.0066(7) 0.0006(7)
C6 0.0340(11) 0.0303(10) 0.0226(9) -0.0069(8) -0.0055(8) 0.0053(8)
C7 0.0160(8) 0.0290(9) 0.0254(9) -0.0009(7) -0.0020(7) 0.0037(7)
C8 0.0214(8) 0.0147(8) 0.0196(8) -0.0024(6) -0.0026(6) 0.0037(6)
C9 0.0288(10) 0.0213(9) 0.0281(10) 0.0049(7) 0.0062(8) 0.0031(7)
C10 0.0419(12) 0.0234(10) 0.0307(10) 0.0092(8) 0.0047(9) 0.0078(8)
C11 0.0340(11) 0.0268(10) 0.0357(11) 0.0060(8) -0.0010(9) 0.0114(8)
C12 0.0253(10) 0.0368(12) 0.0455(13) 0.0129(9) 0.0067(9) 0.0112(8)
C13 0.0234(9) 0.0235(9) 0.0345(10) 0.0100(8) 0.0045(8) 0.0031(7)
C14 0.0307(10) 0.0140(8) 0.0164(8) -0.0012(6) 0.0001(7) 0.0024(7)
C15 0.0520(13) 0.0267(10) 0.0241(10) 0.0046(8) -0.0106(9) -0.0114(9)
C16 0.0829(19) 0.0396(13) 0.0227(11) 0.0080(9) -0.0164(11) -0.0174(12)
C17 0.093(2) 0.0334(12) 0.0199(10) 0.0083(9) 0.0078(12) -0.0071(12)
C18 0.0533(14) 0.0316(11) 0.0352(12) 0.0084(9) 0.0186(11) 0.0013(10)
C19 0.0324(10) 0.0297(10) 0.0238(9) 0.0033(8) 0.0071(8) 0.0034(8)
N1 0.0212(7) 0.0173(7) 0.0133(7) 0.0012(5) 0.0011(5) 0.0031(5)
N2 0.0166(7) 0.0159(7) 0.0156(7) 0.0004(5) -0.0021(5) -0.0002(5)
O1 0.0191(6) 0.0259(6) 0.0144(6) 0.0054(5) 0.0023(5) 0.0066(5)
O2 0.0236(6) 0.0206(6) 0.0239(6) 0.0044(5) 0.0021(5) 0.0015(5)
O3 0.0305(7) 0.0236(7) 0.0327(7) -0.0038(5) -0.0120(6) -0.0038(5)
O4 0.0304(7) 0.0217(7) 0.0279(7) -0.0035(5) 0.0037(6) 0.0075(5)
O5 0.0167(6) 0.0382(8) 0.0368(8) -0.0043(6) 0.0048(6) 0.0022(5)
S1 0.0217(2) 0.0156(2) 0.0200(2) -0.00055(16) -0.00167(16) 0.00036(16)

_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
C1 O1 1.4596(19) . ?
C1 C6 1.520(2) . ?
C1 C4 1.530(2) . ?
C1 C2 1.541(2) . ?
C2 N2 1.487(2) . ?
C2 C7 1.526(2) . ?
C3 N1 1.489(2) . ?
C3 N2 1.493(2) . ?
C3 C14 1.509(2) . ?
C4 C5 1.512(3) . ?
C5 O2 1.472(2) . ?
C7 O5 1.419(2) . ?
C8 C13 1.385(2) . ?
C8 C9 1.391(2) . ?
C8 N1 1.444(2) . ?
C9 C10 1.390(3) . ?
C10 C11 1.373(3) . ?
C11 C12 1.376(3) . ?
C12 C13 1.389(3) . ?
C14 C15 1.382(3) . ?
C14 C19 1.398(3) . ?
C15 C16 1.386(3) . ?
C16 C17 1.377(4) . ?
C17 C18 1.376(3) . ?
C18 C19 1.385(3) . ?
N1 O1 1.4527(17) . ?
N2 S1 1.6141(14) . ?
O2 S1 1.5694(13) . ?
O3 S1 1.4218(13) . ?
O4 S1 1.4274(13) . ?

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 C6 109.29(13) . . ?
O1 C1 C4 102.89(13) . . ?
C6 C1 C4 111.53(15) . . ?
O1 C1 C2 107.37(12) . . ?
C6 C1 C2 110.98(14) . . ?
C4 C1 C2 114.32(14) . . ?
N2 C2 C7 114.47(13) . . ?
N2 C2 C1 107.92(13) . . ?
C7 C2 C1 115.91(14) . . ?
N1 C3 N2 104.74(12) . . ?
N1 C3 C14 111.18(13) . . ?
N2 C3 C14 111.05(13) . . ?
C5 C4 C1 115.66(15) . . ?
O2 C5 C4 111.27(14) . . ?
O5 C7 C2 110.57(14) . . ?
C13 C8 C9 119.79(16) . . ?
C13 C8 N1 122.81(15) . . ?
C9 C8 N1 117.37(15) . . ?
C10 C9 C8 119.74(17) . . ?
C11 C10 C9 120.50(17) . . ?
C10 C11 C12 119.61(18) . . ?
C11 C12 C13 120.95(18) . . ?
C8 C13 C12 119.40(17) . . ?
C15 C14 C19 119.43(17) . . ?
C15 C14 C3 119.30(16) . . ?
C19 C14 C3 121.26(16) . . ?
C14 C15 C16 120.2(2) . . ?
C17 C16 C15 120.2(2) . . ?
C18 C17 C16 120.1(2) . . ?
C17 C18 C19 120.4(2) . . ?
C18 C19 C14 119.69(19) . . ?
C8 N1 O1 107.34(12) . . ?
C8 N1 C3 112.58(12) . . ?
O1 N1 C3 103.90(11) . . ?
C2 N2 C3 114.18(12) . . ?
C2 N2 S1 120.65(11) . . ?
C3 N2 S1 119.30(11) . . ?
N1 O1 C1 109.33(11) . . ?
C5 O2 S1 118.33(10) . . ?
O3 S1 O4 118.42(8) . . ?
O3 S1 O2 111.40(8) . . ?
O4 S1 O2 102.61(7) . . ?
O3 S1 N2 107.71(7) . . ?
O4 S1 N2 110.11(7) . . ?
O2 S1 N2 105.91(7) . . ?

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 39.06(16) . . . . ?
C6 C1 C2 N2 158.44(13) . . . . ?
C4 C1 C2 N2 -74.38(17) . . . . ?
O1 C1 C2 C7 168.93(13) . . . . ?
C6 C1 C2 C7 -71.70(19) . . . . ?
C4 C1 C2 C7 55.49(19) . . . . ?
O1 C1 C4 C5 -58.15(18) . . . . ?
C6 C1 C4 C5 -175.18(14) . . . . ?
C2 C1 C4 C5 57.91(19) . . . . ?
C1 C4 C5 O2 -72.03(19) . . . . ?
N2 C2 C7 O5 -62.43(18) . . . . ?
C1 C2 C7 O5 170.92(14) . . . . ?
C13 C8 C9 C10 1.1(3) . . . . ?
N1 C8 C9 C10 179.27(16) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C9 C8 C13 C12 -0.4(3) . . . . ?
N1 C8 C13 C12 -178.46(18) . . . . ?
C11 C12 C13 C8 -0.3(3) . . . . ?
N1 C3 C14 C15 114.13(17) . . . . ?
N2 C3 C14 C15 -129.67(17) . . . . ?
N1 C3 C14 C19 -65.0(2) . . . . ?
N2 C3 C14 C19 51.2(2) . . . . ?
C19 C14 C15 C16 -0.4(3) . . . . ?
C3 C14 C15 C16 -179.59(18) . . . . ?
C14 C15 C16 C17 0.7(3) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C16 C17 C18 C19 -0.9(3) . . . . ?
C17 C18 C19 C14 1.2(3) . . . . ?
C15 C14 C19 C18 -0.5(3) . . . . ?
C3 C14 C19 C18 178.63(17) . . . . ?
C13 C8 N1 O1 18.0(2) . . . . ?
C9 C8 N1 O1 -160.18(14) . . . . ?
C13 C8 N1 C3 -95.76(19) . . . . ?
C9 C8 N1 C3 86.09(18) . . . . ?
N2 C3 N1 C8 173.38(12) . . . . ?
C14 C3 N1 C8 -66.61(17) . . . . ?
N2 C3 N1 O1 57.57(14) . . . . ?
C14 C3 N1 O1 177.58(13) . . . . ?
C7 C2 N2 C3 167.77(13) . . . . ?
C1 C2 N2 C3 -61.56(16) . . . . ?
C7 C2 N2 S1 -39.41(18) . . . . ?
C1 C2 N2 S1 91.27(14) . . . . ?
N1 C3 N2 C2 10.48(17) . . . . ?
C14 C3 N2 C2 -109.62(15) . . . . ?
N1 C3 N2 S1 -142.74(11) . . . . ?
C14 C3 N2 S1 97.16(14) . . . . ?
C8 N1 O1 C1 158.12(12) . . . . ?
C3 N1 O1 C1 -82.43(14) . . . . ?
C6 C1 O1 N1 -92.98(15) . . . . ?
C4 C1 O1 N1 148.41(12) . . . . ?
C2 C1 O1 N1 27.47(16) . . . . ?
C4 C5 O2 S1 93.31(15) . . . . ?
C5 O2 S1 O3 69.77(13) . . . . ?
C5 O2 S1 O4 -162.53(12) . . . . ?
C5 O2 S1 N2 -47.06(13) . . . . ?
C2 N2 S1 O3 -158.55(12) . . . . ?
C3 N2 S1 O3 -7.08(14) . . . . ?
C2 N2 S1 O4 70.99(13) . . . . ?
C3 N2 S1 O4 -137.54(12) . . . . ?
C2 N2 S1 O2 -39.25(13) . . . . ?
C3 N2 S1 O2 112.21(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5C O4 0.84 2.20 2.8924(19) 140.2 .
O5 H5C S1 0.84 2.99 3.4633(14) 118.2 .

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        29.46
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.064

# Attachment '- ast227s.txt'

data_ast227s
_database_code_depnum_ccdc_archive 'CCDC 750090'
#TrackingRef '- ast227s.txt'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H19 N O5 S'
_chemical_formula_sum            'C11 H19 N O5 S'
_chemical_formula_weight         277.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   12.6837(3)
_cell_length_b                   8.7119(3)
_cell_length_c                   13.9765(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.9650(10)
_cell_angle_gamma                90.00
_cell_volume                     1442.15(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3920
_cell_measurement_theta_min      4.04
_cell_measurement_theta_max      64.54

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    2.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4548
_exptl_absorpt_correction_T_max  0.7273
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            9833
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_sigmaI/netI    0.0132
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.04
_diffrn_reflns_theta_max         64.78
_reflns_number_total             2426
_reflns_number_gt                2214
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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^)+(0.1250P)^2^+2.6510P] 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         2426
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0650
_refine_ls_wR_factor_ref         0.1965
_refine_ls_wR_factor_gt          0.1919
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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
C1 C 0.1493(3) 0.3437(5) 0.7334(2) 0.0398(8) Uani 1 1 d . . .
H1A H 0.1424 0.4226 0.6825 0.048 Uiso 1 1 calc R . .
H1B H 0.2124 0.2782 0.7368 0.048 Uiso 1 1 calc R . .
C2 C 0.1716(3) 0.4171(4) 0.8358(3) 0.0349(8) Uani 1 1 d . . .
H2A H 0.0999 0.4482 0.8399 0.042 Uiso 1 1 calc R . .
H2B H 0.2158 0.5093 0.8397 0.042 Uiso 1 1 calc R . .
C3 C 0.2331(3) 0.3173(4) 0.9282(2) 0.0302(7) Uani 1 1 d . . .
C4 C 0.1885(3) 0.3199(4) 1.0154(2) 0.0350(8) Uani 1 1 d . . .
H4A H 0.2428 0.3120 1.0847 0.042 Uiso 1 1 calc R . .
H4B H 0.1237 0.3846 1.0078 0.042 Uiso 1 1 calc R . .
C5 C 0.1702(2) 0.1819(4) 0.9485(2) 0.0265(7) Uani 1 1 d . . .
C6 C 0.2030(3) -0.0316(4) 1.0577(2) 0.0292(7) Uani 1 1 d . . .
C7 C 0.2811(3) -0.1661(4) 1.1050(2) 0.0324(7) Uani 1 1 d . . .
C8 C 0.3590(3) 0.3009(5) 0.9520(3) 0.0413(9) Uani 1 1 d . . .
H8A H 0.3912 0.2362 1.0109 0.062 Uiso 1 1 calc R . .
H8B H 0.3940 0.4003 0.9658 0.062 Uiso 1 1 calc R . .
H8C H 0.3717 0.2560 0.8943 0.062 Uiso 1 1 calc R . .
C9 C 0.3886(5) -0.1007(7) 1.1818(6) 0.112(3) Uani 1 1 d . . .
H9A H 0.3910 -0.1216 1.2500 0.169 Uiso 1 1 calc R . .
H9B H 0.3905 0.0082 1.1722 0.169 Uiso 1 1 calc R . .
H9C H 0.4526 -0.1474 1.1720 0.169 Uiso 1 1 calc R . .
C10 C 0.2256(5) -0.2714(7) 1.1592(5) 0.089(2) Uani 1 1 d . . .
H10A H 0.1527 -0.3018 1.1124 0.133 Uiso 1 1 calc R . .
H10B H 0.2173 -0.2183 1.2163 0.133 Uiso 1 1 calc R . .
H10C H 0.2718 -0.3608 1.1834 0.133 Uiso 1 1 calc R . .
C11 C 0.3094(7) -0.2547(7) 1.0240(4) 0.103(3) Uani 1 1 d . . .
H11A H 0.2466 -0.3186 0.9863 0.154 Uiso 1 1 calc R . .
H11B H 0.3746 -0.3177 1.0564 0.154 Uiso 1 1 calc R . .
H11C H 0.3249 -0.1841 0.9780 0.154 Uiso 1 1 calc R . .
N1 N 0.0614(2) 0.1478(3) 0.87639(19) 0.0274(6) Uani 1 1 d . . .
H1C H 0.0026 0.1550 0.8932 0.033 Uiso 1 1 calc R . .
O1 O 0.0462(2) 0.2528(3) 0.70287(18) 0.0441(7) Uani 1 1 d . . .
O2 O -0.0587(2) 0.0377(4) 0.7121(2) 0.0529(7) Uani 1 1 d . . .
O3 O 0.1472(2) 0.0176(3) 0.7632(2) 0.0523(7) Uani 1 1 d . . .
O4 O 0.23804(17) 0.0511(3) 0.99244(16) 0.0304(5) Uani 1 1 d . . .
O5 O 0.11875(18) 0.0011(3) 1.07396(18) 0.0358(6) Uani 1 1 d . . .
S1 S 0.04974(6) 0.09507(10) 0.76169(6) 0.0353(3) Uani 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
C1 0.0332(17) 0.056(2) 0.0290(17) 0.0070(15) 0.0103(14) -0.0075(16)
C2 0.0361(18) 0.0339(18) 0.0351(17) 0.0044(14) 0.0130(14) -0.0024(13)
C3 0.0307(16) 0.0341(17) 0.0237(15) -0.0013(13) 0.0070(12) -0.0069(13)
C4 0.0403(18) 0.0392(19) 0.0259(15) -0.0035(14) 0.0123(14) -0.0060(15)
C5 0.0249(15) 0.0304(16) 0.0252(14) 0.0013(12) 0.0101(12) 0.0008(12)
C6 0.0254(15) 0.0334(17) 0.0269(15) 0.0003(12) 0.0072(12) -0.0038(13)
C7 0.0299(16) 0.0341(18) 0.0326(16) 0.0022(13) 0.0106(13) 0.0041(13)
C8 0.0293(17) 0.054(2) 0.0368(18) 0.0057(16) 0.0068(14) -0.0112(15)
C9 0.071(4) 0.061(3) 0.135(6) 0.008(3) -0.049(4) 0.009(3)
C10 0.076(3) 0.079(4) 0.130(5) 0.066(4) 0.058(4) 0.038(3)
C11 0.176(7) 0.078(4) 0.063(3) 0.018(3) 0.053(4) 0.072(5)
N1 0.0212(12) 0.0344(14) 0.0275(13) -0.0010(11) 0.0099(10) -0.0003(10)
O1 0.0392(13) 0.0551(16) 0.0324(13) 0.0028(11) 0.0058(10) -0.0048(12)
O2 0.0401(15) 0.0698(19) 0.0399(14) -0.0114(14) 0.0035(11) -0.0138(13)
O3 0.0502(16) 0.0628(18) 0.0476(15) -0.0106(13) 0.0219(13) 0.0072(13)
O4 0.0246(11) 0.0363(12) 0.0313(11) 0.0066(9) 0.0111(9) 0.0016(9)
O5 0.0282(11) 0.0420(13) 0.0411(13) 0.0115(10) 0.0170(10) 0.0042(10)
S1 0.0296(5) 0.0455(6) 0.0299(5) -0.0101(3) 0.0096(3) -0.0066(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
C1 O1 1.457(4) . ?
C1 C2 1.499(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.521(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C5 1.506(4) . ?
C3 C4 1.516(4) . ?
C3 C8 1.518(4) . ?
C4 C5 1.489(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N1 1.419(4) . ?
C5 O4 1.427(4) . ?
C6 O5 1.204(4) . ?
C6 O4 1.356(4) . ?
C6 C7 1.523(4) . ?
C7 C9 1.513(6) . ?
C7 C10 1.514(6) . ?
C7 C11 1.516(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N1 S1 1.623(3) . ?
N1 H1C 0.8600 . ?
O1 S1 1.594(3) . ?
O2 S1 1.393(3) . ?
O3 S1 1.402(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
O1 C1 C2 110.7(3) . . ?
O1 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
C1 C2 C3 115.6(3) . . ?
C1 C2 H2A 108.4 . . ?
C3 C2 H2A 108.4 . . ?
C1 C2 H2B 108.4 . . ?
C3 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
C5 C3 C4 59.1(2) . . ?
C5 C3 C8 118.2(3) . . ?
C4 C3 C8 119.5(3) . . ?
C5 C3 C2 117.6(3) . . ?
C4 C3 C2 116.7(3) . . ?
C8 C3 C2 114.8(3) . . ?
C5 C4 C3 60.1(2) . . ?
C5 C4 H4A 117.8 . . ?
C3 C4 H4A 117.8 . . ?
C5 C4 H4B 117.8 . . ?
C3 C4 H4B 117.8 . . ?
H4A C4 H4B 114.9 . . ?
N1 C5 O4 115.0(3) . . ?
N1 C5 C4 120.5(3) . . ?
O4 C5 C4 116.1(3) . . ?
N1 C5 C3 118.4(3) . . ?
O4 C5 C3 115.3(2) . . ?
C4 C5 C3 60.8(2) . . ?
O5 C6 O4 121.9(3) . . ?
O5 C6 C7 125.7(3) . . ?
O4 C6 C7 112.5(2) . . ?
C9 C7 C10 109.5(5) . . ?
C9 C7 C11 109.1(5) . . ?
C10 C7 C11 110.0(5) . . ?
C9 C7 C6 107.4(3) . . ?
C10 C7 C6 109.7(3) . . ?
C11 C7 C6 111.0(3) . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 N1 S1 118.8(2) . . ?
C5 N1 H1C 120.6 . . ?
S1 N1 H1C 120.6 . . ?
C1 O1 S1 117.4(2) . . ?
C6 O4 C5 114.9(2) . . ?
O2 S1 O3 122.92(19) . . ?
O2 S1 O1 102.24(17) . . ?
O3 S1 O1 106.56(17) . . ?
O2 S1 N1 108.51(15) . . ?
O3 S1 N1 110.69(15) . . ?
O1 S1 N1 103.96(14) . . ?

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 C3 84.5(4) . . . . ?
C1 C2 C3 C5 -69.1(4) . . . . ?
C1 C2 C3 C4 -136.3(3) . . . . ?
C1 C2 C3 C8 76.7(4) . . . . ?
C8 C3 C4 C5 -107.1(3) . . . . ?
C2 C3 C4 C5 107.6(3) . . . . ?
C3 C4 C5 N1 -107.7(3) . . . . ?
C3 C4 C5 O4 105.8(3) . . . . ?
C4 C3 C5 N1 111.0(3) . . . . ?
C8 C3 C5 N1 -139.7(3) . . . . ?
C2 C3 C5 N1 4.9(4) . . . . ?
C4 C3 C5 O4 -107.0(3) . . . . ?
C8 C3 C5 O4 2.2(4) . . . . ?
C2 C3 C5 O4 146.9(3) . . . . ?
C8 C3 C5 C4 109.2(3) . . . . ?
C2 C3 C5 C4 -106.1(3) . . . . ?
O5 C6 C7 C9 -107.9(5) . . . . ?
O4 C6 C7 C9 72.5(5) . . . . ?
O5 C6 C7 C10 11.1(5) . . . . ?
O4 C6 C7 C10 -168.5(4) . . . . ?
O5 C6 C7 C11 132.8(5) . . . . ?
O4 C6 C7 C11 -46.8(5) . . . . ?
O4 C5 N1 S1 -77.2(3) . . . . ?
C4 C5 N1 S1 136.0(2) . . . . ?
C3 C5 N1 S1 64.9(3) . . . . ?
C2 C1 O1 S1 -72.6(3) . . . . ?
O5 C6 O4 C5 2.4(4) . . . . ?
C7 C6 O4 C5 -177.9(2) . . . . ?
N1 C5 O4 C6 -70.0(3) . . . . ?
C4 C5 O4 C6 78.3(3) . . . . ?
C3 C5 O4 C6 146.7(3) . . . . ?
C1 O1 S1 O2 -178.1(2) . . . . ?
C1 O1 S1 O3 -48.0(3) . . . . ?
C1 O1 S1 N1 69.0(3) . . . . ?
C5 N1 S1 O2 167.8(2) . . . . ?
C5 N1 S1 O3 30.1(3) . . . . ?
C5 N1 S1 O1 -83.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1C O5 0.86 2.22 2.919(3) 138.1 3_557

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        64.78
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.154
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.078