Supplementary Material for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2007

data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Hartmut Redlich'
_publ_contact_author_address     
;
Institute of Organic Chemistry
Correnstrasse, 40
Muenster
D-48149
GERMANY
;

_publ_contact_author_email       REDLICH@UNI-MUENSTER.DE

_publ_section_title              
;
Protection Controlled Intramolecular Regioselective
Anionic Cyclizations of Stabilized Dilithiated 6,7-Anhydro-Heptose
1,1-Trimethylene Dithioacetal Derived from D-Glucosamine: Formation of
Six- and Seven-membered Amino Carbasugars. Synthesis of (-)-Calystegine
B3
;
loop_
_publ_author_name
'Hartmut Redlich'
'Klaus Bergander'
'Yue-Lei Chen'
'Roland Frohlich'

data_red3679
_database_code_depnum_ccdc_archive 'CCDC 648111'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H22 F3 N O6 S2'
_chemical_formula_weight         433.46

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'
F F 0.0727 0.0534 '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           tetragonal
_symmetry_space_group_name_H-M   P41212

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   9.905(1)
_cell_length_b                   9.905(1)
_cell_length_c                   39.488(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3874.1(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5012
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      66.60

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1808
_exptl_absorpt_coefficient_mu    3.055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4144
_exptl_absorpt_correction_T_max  0.6572
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24194
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         4.48
_diffrn_reflns_theta_max         66.40
_reflns_number_total             2937
_reflns_number_gt                2802
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SCHAKAL (Keller, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.0891P)^2^+2.3141P] 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    riding
_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   0.02(3)
_refine_ls_number_reflns         2937
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1405
_refine_ls_wR_factor_gt          0.1370
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 -0.0108(4) 0.3289(4) 0.15755(8) 0.0452(8) Uani 1 1 d . . .
C2 C -0.1055(3) 0.4319(3) 0.17506(8) 0.0418(7) Uani 1 1 d . . .
H2 H -0.1529 0.4811 0.1571 0.050 Uiso 1 1 calc R . .
N2 N -0.0302(3) 0.5309(3) 0.19472(7) 0.0494(8) Uani 1 1 d . . .
H21 H 0.007(5) 0.507(5) 0.2127(11) 0.059 Uiso 1 1 d . . .
C21 C -0.0446(4) 0.6622(4) 0.18947(9) 0.0511(9) Uani 1 1 d . . .
O21 O -0.1097(4) 0.7166(3) 0.16760(8) 0.0762(9) Uani 1 1 d . . .
C22 C 0.0332(5) 0.7504(5) 0.21526(11) 0.0694(12) Uani 1 1 d . . .
F1 F -0.0230(4) 0.7480(4) 0.24485(7) 0.1243(14) Uani 1 1 d . . .
F2 F 0.1565(4) 0.7058(4) 0.22037(10) 0.1120(12) Uani 1 1 d . . .
F3 F 0.0455(4) 0.8735(3) 0.20473(9) 0.1115(12) Uani 1 1 d . . .
C3 C -0.2126(4) 0.3671(3) 0.19748(8) 0.0464(8) Uani 1 1 d . . .
H3 H -0.1707 0.3087 0.2145 0.056 Uiso 1 1 calc R . .
O3 O -0.2917(3) 0.4715(3) 0.21340(7) 0.0647(8) Uani 1 1 d . . .
C4 C -0.3177(4) 0.2888(4) 0.17694(8) 0.0475(8) Uani 1 1 d . . .
H4 H -0.3203 0.3258 0.1539 0.057 Uiso 1 1 calc R . .
O4 O -0.4409(3) 0.3189(3) 0.19322(7) 0.0605(7) Uani 1 1 d . . .
C41 C -0.4260(5) 0.4544(5) 0.20259(13) 0.0720(12) Uani 1 1 d . . .
H41A H -0.4880 0.4766 0.2208 0.086 Uiso 1 1 calc R . .
H41B H -0.4449 0.5129 0.1835 0.086 Uiso 1 1 calc R . .
C5 C -0.2936(4) 0.1382(4) 0.17480(8) 0.0461(8) Uani 1 1 d . . .
H5 H -0.3591 0.0993 0.1590 0.055 Uiso 1 1 calc R . .
C6 C -0.1523(4) 0.1045(4) 0.16253(8) 0.0503(9) Uani 1 1 d . . .
H6 H -0.0946 0.0907 0.1824 0.060 Uiso 1 1 calc R . .
O6 O -0.1540(4) -0.0177(3) 0.14336(7) 0.0692(8) Uani 1 1 d . . .
H6A H -0.1396 -0.0819 0.1560 0.104 Uiso 1 1 calc R . .
C7 C -0.0866(4) 0.2111(4) 0.14005(8) 0.0508(9) Uani 1 1 d . . .
H7A H -0.1564 0.2498 0.1258 0.061 Uiso 1 1 calc R . .
H7B H -0.0232 0.1656 0.1252 0.061 Uiso 1 1 calc R . .
O8 O -0.3089(3) 0.0731(3) 0.20706(6) 0.0545(6) Uani 1 1 d . . .
C9 C -0.4419(4) 0.0428(4) 0.21720(9) 0.0585(10) Uani 1 1 d . . .
H9A H -0.4818 0.1207 0.2282 0.070 Uiso 1 1 calc R . .
H9B H -0.4962 0.0206 0.1975 0.070 Uiso 1 1 calc R . .
O10 O -0.4395(3) -0.0649(3) 0.23926(6) 0.0607(7) Uani 1 1 d . . .
C11 C -0.4051(7) -0.1901(5) 0.22452(13) 0.0893(16) Uani 1 1 d . . .
H11A H -0.4785 -0.2211 0.2107 0.134 Uiso 1 1 calc R . .
H11B H -0.3875 -0.2548 0.2421 0.134 Uiso 1 1 calc R . .
H11C H -0.3259 -0.1793 0.2108 0.134 Uiso 1 1 calc R . .
S12 S 0.11135(11) 0.26498(13) 0.18868(2) 0.0677(3) Uani 1 1 d . . .
C13 C 0.2387(7) 0.1923(8) 0.16313(19) 0.119(2) Uani 1 1 d . . .
H13A H 0.3061 0.1515 0.1777 0.142 Uiso 1 1 calc R . .
H13B H 0.1989 0.1208 0.1496 0.142 Uiso 1 1 calc R . .
C14 C 0.3101(6) 0.2935(7) 0.13902(16) 0.1009(19) Uani 1 1 d . . .
H14A H 0.3345 0.3753 0.1511 0.121 Uiso 1 1 calc R . .
H14B H 0.3912 0.2539 0.1295 0.121 Uiso 1 1 calc R . .
C15 C 0.2123(5) 0.3227(6) 0.11254(14) 0.0847(15) Uani 1 1 d . . .
H15A H 0.1754 0.2380 0.1044 0.102 Uiso 1 1 calc R . .
H15B H 0.2592 0.3650 0.0937 0.102 Uiso 1 1 calc R . .
S16 S 0.07456(10) 0.43047(12) 0.12515(2) 0.0631(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 0.050(2) 0.045(2) 0.0396(15) 0.0018(14) -0.0038(14) 0.0062(16)
C2 0.0471(18) 0.0384(17) 0.0399(16) 0.0010(13) -0.0074(14) 0.0046(15)
N2 0.0569(18) 0.0476(19) 0.0437(14) 0.0003(13) -0.0103(14) 0.0015(14)
C21 0.054(2) 0.046(2) 0.0531(19) -0.0039(17) -0.0029(18) -0.0024(17)
O21 0.108(3) 0.0447(15) 0.0761(18) 0.0013(14) -0.0342(19) 0.0049(15)
C22 0.092(4) 0.056(3) 0.060(2) -0.006(2) -0.012(2) -0.013(2)
F1 0.169(4) 0.137(3) 0.0670(17) -0.0411(19) 0.022(2) -0.052(3)
F2 0.094(2) 0.105(2) 0.137(3) -0.020(2) -0.051(2) -0.0118(19)
F3 0.160(3) 0.0573(17) 0.117(2) -0.0013(17) -0.046(2) -0.0260(19)
C3 0.057(2) 0.0410(19) 0.0415(15) -0.0031(14) -0.0005(15) 0.0036(16)
O3 0.0686(19) 0.0588(16) 0.0667(16) -0.0187(14) 0.0090(14) 0.0079(14)
C4 0.053(2) 0.048(2) 0.0410(16) 0.0025(16) -0.0047(15) 0.0016(16)
O4 0.0475(15) 0.0606(17) 0.0735(17) -0.0019(13) 0.0028(13) 0.0045(12)
C41 0.063(3) 0.065(3) 0.088(3) -0.011(2) 0.009(2) 0.017(2)
C5 0.056(2) 0.047(2) 0.0354(15) -0.0004(14) -0.0114(14) -0.0023(16)
C6 0.068(2) 0.0435(19) 0.0391(15) -0.0089(15) -0.0103(16) 0.0073(17)
O6 0.105(3) 0.0466(15) 0.0557(14) -0.0135(12) -0.0060(16) 0.0097(15)
C7 0.059(2) 0.056(2) 0.0379(15) -0.0046(15) -0.0045(16) 0.0134(18)
O8 0.0669(17) 0.0547(15) 0.0418(11) 0.0070(11) -0.0081(11) -0.0052(12)
C9 0.067(3) 0.059(2) 0.0500(19) 0.0063(18) 0.0004(18) 0.0001(19)
O10 0.087(2) 0.0515(15) 0.0440(12) -0.0027(11) 0.0065(13) -0.0043(14)
C11 0.132(5) 0.054(3) 0.081(3) -0.005(2) 0.026(3) 0.000(3)
S12 0.0622(7) 0.0842(8) 0.0567(5) 0.0085(5) -0.0151(5) 0.0229(5)
C13 0.108(5) 0.125(5) 0.123(5) -0.014(4) -0.026(4) 0.045(4)
C14 0.059(3) 0.127(5) 0.117(4) 0.015(4) 0.018(3) 0.035(3)
C15 0.066(3) 0.096(4) 0.092(3) -0.027(3) 0.026(3) -0.004(3)
S16 0.0577(6) 0.0770(7) 0.0544(5) 0.0142(5) 0.0068(4) 0.0068(5)

_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 C2 1.548(5) . ?
C1 C7 1.550(5) . ?
C1 S16 1.835(4) . ?
C1 S12 1.838(3) . ?
C2 N2 1.456(5) . ?
C2 C3 1.524(5) . ?
N2 C21 1.325(5) . ?
C21 O21 1.205(5) . ?
C21 C22 1.547(5) . ?
C22 F3 1.294(5) . ?
C22 F1 1.295(6) . ?
C22 F2 1.315(6) . ?
C3 O3 1.442(4) . ?
C3 C4 1.530(5) . ?
O3 C41 1.408(6) . ?
C4 O4 1.411(5) . ?
C4 C5 1.513(5) . ?
O4 C41 1.400(5) . ?
C5 O8 1.436(4) . ?
C5 C6 1.518(6) . ?
C6 O6 1.428(4) . ?
C6 C7 1.526(5) . ?
O8 C9 1.409(5) . ?
C9 O10 1.378(5) . ?
O10 C11 1.411(5) . ?
S12 C13 1.769(7) . ?
C13 C14 1.553(10) . ?
C14 C15 1.454(8) . ?
C15 S16 1.803(5) . ?

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
C2 C1 C7 113.7(3) . . ?
C2 C1 S16 103.2(2) . . ?
C7 C1 S16 109.0(2) . . ?
C2 C1 S12 109.1(2) . . ?
C7 C1 S12 111.0(2) . . ?
S16 C1 S12 110.6(2) . . ?
N2 C2 C3 109.3(3) . . ?
N2 C2 C1 111.8(3) . . ?
C3 C2 C1 113.8(3) . . ?
C21 N2 C2 121.5(3) . . ?
O21 C21 N2 127.5(4) . . ?
O21 C21 C22 119.1(4) . . ?
N2 C21 C22 113.5(3) . . ?
F3 C22 F1 110.4(4) . . ?
F3 C22 F2 106.2(4) . . ?
F1 C22 F2 104.7(4) . . ?
F3 C22 C21 111.6(4) . . ?
F1 C22 C21 111.7(4) . . ?
F2 C22 C21 111.9(4) . . ?
O3 C3 C2 109.2(3) . . ?
O3 C3 C4 103.0(3) . . ?
C2 C3 C4 112.3(3) . . ?
C41 O3 C3 107.2(3) . . ?
O4 C4 C5 111.7(3) . . ?
O4 C4 C3 103.9(3) . . ?
C5 C4 C3 114.9(3) . . ?
C41 O4 C4 103.4(3) . . ?
O4 C41 O3 107.2(3) . . ?
O8 C5 C4 112.1(3) . . ?
O8 C5 C6 106.3(3) . . ?
C4 C5 C6 112.4(3) . . ?
O6 C6 C5 110.2(3) . . ?
O6 C6 C7 106.4(3) . . ?
C5 C6 C7 115.3(3) . . ?
C6 C7 C1 117.9(3) . . ?
C9 O8 C5 116.5(3) . . ?
O10 C9 O8 109.2(3) . . ?
C9 O10 C11 115.1(3) . . ?
C13 S12 C1 103.2(3) . . ?
C14 C13 S12 114.3(5) . . ?
C15 C14 C13 105.4(5) . . ?
C14 C15 S16 115.0(4) . . ?
C15 S16 C1 102.5(2) . . ?

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
C7 C1 C2 N2 172.8(3) . . . . ?
S16 C1 C2 N2 -69.3(3) . . . . ?
S12 C1 C2 N2 48.3(3) . . . . ?
C7 C1 C2 C3 48.3(4) . . . . ?
S16 C1 C2 C3 166.2(2) . . . . ?
S12 C1 C2 C3 -76.1(3) . . . . ?
C3 C2 N2 C21 -108.6(4) . . . . ?
C1 C2 N2 C21 124.5(4) . . . . ?
C2 N2 C21 O21 -5.5(7) . . . . ?
C2 N2 C21 C22 174.2(3) . . . . ?
O21 C21 C22 F3 -16.5(7) . . . . ?
N2 C21 C22 F3 163.7(4) . . . . ?
O21 C21 C22 F1 107.6(5) . . . . ?
N2 C21 C22 F1 -72.2(5) . . . . ?
O21 C21 C22 F2 -135.3(4) . . . . ?
N2 C21 C22 F2 44.9(5) . . . . ?
N2 C2 C3 O3 52.2(4) . . . . ?
C1 C2 C3 O3 178.0(3) . . . . ?
N2 C2 C3 C4 165.8(3) . . . . ?
C1 C2 C3 C4 -68.4(4) . . . . ?
C2 C3 O3 C41 118.9(4) . . . . ?
C4 C3 O3 C41 -0.6(4) . . . . ?
O3 C3 C4 O4 -22.5(3) . . . . ?
C2 C3 C4 O4 -139.9(3) . . . . ?
O3 C3 C4 C5 -144.9(3) . . . . ?
C2 C3 C4 C5 97.8(3) . . . . ?
C5 C4 O4 C41 161.6(3) . . . . ?
C3 C4 O4 C41 37.1(4) . . . . ?
C4 O4 C41 O3 -39.0(4) . . . . ?
C3 O3 C41 O4 24.2(5) . . . . ?
O4 C4 C5 O8 -51.2(4) . . . . ?
C3 C4 C5 O8 66.9(4) . . . . ?
O4 C4 C5 C6 -170.9(3) . . . . ?
C3 C4 C5 C6 -52.8(4) . . . . ?
O8 C5 C6 O6 89.4(3) . . . . ?
C4 C5 C6 O6 -147.5(3) . . . . ?
O8 C5 C6 C7 -150.1(3) . . . . ?
C4 C5 C6 C7 -27.1(4) . . . . ?
O6 C6 C7 C1 -151.9(3) . . . . ?
C5 C6 C7 C1 85.6(4) . . . . ?
C2 C1 C7 C6 -72.0(4) . . . . ?
S16 C1 C7 C6 173.5(3) . . . . ?
S12 C1 C7 C6 51.5(4) . . . . ?
C4 C5 O8 C9 81.6(4) . . . . ?
C6 C5 O8 C9 -155.3(3) . . . . ?
C5 O8 C9 O10 154.1(3) . . . . ?
O8 C9 O10 C11 -69.8(5) . . . . ?
C2 C1 S12 C13 -163.0(4) . . . . ?
C7 C1 S12 C13 70.9(4) . . . . ?
S16 C1 S12 C13 -50.2(3) . . . . ?
C1 S12 C13 C14 61.3(5) . . . . ?
S12 C13 C14 C15 -73.1(6) . . . . ?
C13 C14 C15 S16 73.8(6) . . . . ?
C14 C15 S16 C1 -63.5(5) . . . . ?
C2 C1 S16 C15 166.0(3) . . . . ?
C7 C1 S16 C15 -72.8(3) . . . . ?
S12 C1 S16 C15 49.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.890
_diffrn_reflns_theta_full        66.40
_diffrn_measured_fraction_theta_full 0.890
_refine_diff_density_max         0.927
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.054