# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2008



data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Peter Langer'
_publ_contact_author_email       PETER.LANGER@UNI-ROSTOCK.DE

_publ_section_title              
;
Regioselective Synthesis of Functionalized
3,5-Diketoesters and 2,4-Diketosulfones by Uncatalyzed Condensation
of 1,3-Bis(trimethylsilyloxy)-1,3-butadienes with alpha,beta-Unsaturated
Acid Chlorides and Sulfonyl Chlorides
;
loop_
_publ_author_name
'Peter Langer'
'T. H. Tam Dang'
'Christine Fischer'
'Thomas Rahn'
'Anke Spannenberg'

# Attachment 'ks580m.cif'

data_ks580m
_database_code_depnum_ccdc_archive 'CCDC 691729'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H11 Cl O5 S'
_chemical_formula_weight         290.71

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'
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'
Cl Cl 0.1484 0.1585 '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)/c

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

_cell_length_a                   15.488(3)
_cell_length_b                   8.5440(17)
_cell_length_c                   10.372(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.95(3)
_cell_angle_gamma                90.00
_cell_volume                     1298.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2000
_cell_measurement_theta_min      4
_cell_measurement_theta_max      20

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.464
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_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  'STOE-IPDS I'
_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            4553
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0706
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         25.96
_reflns_number_total             2525
_reflns_number_gt                1438
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       STOE-EXPOSE
_computing_cell_refinement       STOE-CELL
_computing_data_reduction        STOE-INTEGRATE
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    XP
_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^)+(0.0554P)^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         2525
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1065
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   0.852
_refine_ls_restrained_S_all      0.852
_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
Cl1 Cl 0.47550(6) 0.39143(16) 1.20699(13) 0.1219(5) Uani 1 1 d . . .
S1 S 0.08997(5) 0.14708(8) 0.86242(7) 0.0459(2) Uani 1 1 d . . .
O1 O 0.07957(13) -0.0074(2) 0.9089(2) 0.0617(6) Uani 1 1 d . . .
O2 O 0.08424(14) 0.1685(3) 0.72305(18) 0.0682(6) Uani 1 1 d . . .
O3 O -0.10912(14) 0.1388(2) 0.7293(2) 0.0703(6) Uani 1 1 d . . .
O4 O -0.30048(15) 0.1883(3) 0.7720(3) 0.1051(10) Uani 1 1 d . . .
O5 O -0.27791(13) 0.4075(2) 0.6782(2) 0.0705(7) Uani 1 1 d . . .
C1 C 0.19639(16) 0.2231(3) 0.9654(3) 0.0422(6) Uani 1 1 d . . .
C2 C 0.2454(2) 0.1468(4) 1.0818(3) 0.0601(8) Uani 1 1 d . . .
H2B H 0.2213 0.0586 1.1100 0.072 Uiso 1 1 calc R . .
C3 C 0.3308(2) 0.2004(4) 1.1576(3) 0.0730(10) Uani 1 1 d . . .
H3A H 0.3643 0.1489 1.2371 0.088 Uiso 1 1 calc R . .
C4 C 0.3655(2) 0.3284(4) 1.1156(4) 0.0663(9) Uani 1 1 d . . .
C5 C 0.3174(2) 0.4080(4) 1.0016(4) 0.0787(11) Uani 1 1 d . . .
H5A H 0.3417 0.4974 0.9755 0.094 Uiso 1 1 calc R . .
C6 C 0.2318(2) 0.3550(4) 0.9249(3) 0.0667(9) Uani 1 1 d . . .
H6A H 0.1983 0.4081 0.8463 0.080 Uiso 1 1 calc R . .
C7 C 0.00956(16) 0.2744(3) 0.8988(3) 0.0450(7) Uani 1 1 d . . .
H7A H 0.0181 0.2701 0.9956 0.054 Uiso 1 1 calc R . .
H7B H 0.0214 0.3810 0.8769 0.054 Uiso 1 1 calc R . .
C8 C -0.08836(17) 0.2335(3) 0.8202(3) 0.0455(7) Uani 1 1 d . . .
C9 C -0.15784(17) 0.3209(3) 0.8659(3) 0.0508(7) Uani 1 1 d . . .
H9A H -0.1546 0.2855 0.9563 0.061 Uiso 1 1 calc R . .
H9B H -0.1436 0.4318 0.8713 0.061 Uiso 1 1 calc R . .
C10 C -0.25314(19) 0.2961(4) 0.7694(3) 0.0532(8) Uani 1 1 d . . .
C11 C -0.3667(2) 0.3905(4) 0.5740(4) 0.0898(12) Uani 1 1 d . . .
H11A H -0.3777 0.4784 0.5131 0.135 Uiso 1 1 calc R . .
H11B H -0.4133 0.3861 0.6164 0.135 Uiso 1 1 calc R . .
H11C H -0.3677 0.2958 0.5236 0.135 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
Cl1 0.0525(6) 0.1500(11) 0.1487(11) -0.0489(8) 0.0129(6) -0.0226(6)
S1 0.0491(4) 0.0480(4) 0.0346(4) -0.0041(3) 0.0053(3) 0.0086(3)
O1 0.0595(12) 0.0438(11) 0.0715(14) 0.0000(10) 0.0071(10) 0.0023(10)
O2 0.0736(14) 0.0938(16) 0.0318(11) -0.0050(11) 0.0099(9) 0.0200(12)
O3 0.0596(13) 0.0681(14) 0.0662(15) -0.0292(12) -0.0030(10) -0.0044(11)
O4 0.0548(15) 0.0918(18) 0.141(2) 0.0574(17) -0.0066(14) -0.0206(13)
O5 0.0545(13) 0.0744(14) 0.0755(15) 0.0304(12) 0.0113(11) -0.0021(11)
C1 0.0454(15) 0.0421(15) 0.0391(16) 0.0003(12) 0.0138(12) 0.0059(12)
C2 0.0593(19) 0.0603(18) 0.0517(19) 0.0121(16) 0.0057(15) 0.0044(16)
C3 0.0533(19) 0.086(3) 0.065(2) 0.0072(19) 0.0001(16) 0.0084(18)
C4 0.0449(17) 0.072(2) 0.079(2) -0.0184(19) 0.0152(17) 0.0022(16)
C5 0.065(2) 0.063(2) 0.110(3) 0.001(2) 0.031(2) -0.0167(18)
C6 0.069(2) 0.062(2) 0.065(2) 0.0185(18) 0.0180(17) 0.0077(17)
C7 0.0438(15) 0.0503(16) 0.0329(15) -0.0090(12) 0.0015(11) 0.0030(13)
C8 0.0445(16) 0.0466(16) 0.0374(16) 0.0018(13) 0.0024(13) -0.0012(13)
C9 0.0470(16) 0.0574(18) 0.0474(17) 0.0036(14) 0.0144(13) -0.0018(13)
C10 0.0429(16) 0.0531(18) 0.060(2) 0.0121(15) 0.0117(14) -0.0004(14)
C11 0.052(2) 0.123(3) 0.080(3) 0.036(2) 0.0023(18) 0.014(2)

_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
Cl1 C4 1.744(3) . ?
S1 O2 1.431(2) . ?
S1 O1 1.432(2) . ?
S1 C1 1.771(3) . ?
S1 C7 1.784(3) . ?
O3 C8 1.205(3) . ?
O4 C10 1.183(3) . ?
O5 C10 1.308(3) . ?
O5 C11 1.454(3) . ?
C1 C2 1.366(4) . ?
C1 C6 1.377(4) . ?
C2 C3 1.379(4) . ?
C3 C4 1.352(5) . ?
C4 C5 1.358(5) . ?
C5 C6 1.382(4) . ?
C7 C8 1.511(3) . ?
C8 C9 1.507(4) . ?
C9 C10 1.505(4) . ?

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
O2 S1 O1 118.75(13) . . ?
O2 S1 C1 107.61(13) . . ?
O1 S1 C1 108.63(12) . . ?
O2 S1 C7 108.48(13) . . ?
O1 S1 C7 109.18(13) . . ?
C1 S1 C7 103.04(12) . . ?
C10 O5 C11 116.7(2) . . ?
C2 C1 C6 119.9(3) . . ?
C2 C1 S1 120.0(2) . . ?
C6 C1 S1 120.1(2) . . ?
C1 C2 C3 120.0(3) . . ?
C4 C3 C2 119.6(3) . . ?
C3 C4 C5 121.5(3) . . ?
C3 C4 Cl1 119.7(3) . . ?
C5 C4 Cl1 118.8(3) . . ?
C4 C5 C6 119.3(3) . . ?
C1 C6 C5 119.7(3) . . ?
C8 C7 S1 113.09(18) . . ?
O3 C8 C9 122.9(2) . . ?
O3 C8 C7 122.9(3) . . ?
C9 C8 C7 114.2(2) . . ?
C10 C9 C8 111.5(2) . . ?
O4 C10 O5 123.0(3) . . ?
O4 C10 C9 125.1(3) . . ?
O5 C10 C9 111.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.96
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.045