# 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        'Patrick Riss'
_publ_contact_author_email       RISS@UNI-MAINZ.DE

_publ_section_title              
;
A convenient chemo-enzymatic synthesis of both enantiomers of trans-1-
toluenesulfonyloxymethyl-2-fluoromethyl-cyclopropane
;
loop_
_publ_author_name
'Patrick Riss'
'Frank Rosch'

# Attachment 'diethyl (S,S)-cyclopropane-1,2- dicarboxylate_cif.txt'

data_cpde
_database_code_depnum_ccdc_archive 'CCDC 691513'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            
'Cyclopropane-1,2-dicarboxylic acid diethyl ester'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H14 O4'
_chemical_formula_weight         186.20

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'C 2 2 21'

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

_cell_length_a                   7.042(3)
_cell_length_b                   18.432(2)
_cell_length_c                   15.5238(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2014.9(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    22
_cell_measurement_theta_min      37
_cell_measurement_theta_max      47

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.51
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.6260
_exptl_absorpt_correction_T_max  0.6835
_exptl_absorpt_process_details   'Corinc (Dr\"ager, 1971)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CAD4 Enraf Nonius'
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_method       \w/2\q
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        1
_diffrn_reflns_number            2091
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.80
_diffrn_reflns_theta_max         69.88
_reflns_number_total             1816
_reflns_number_gt                1746
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Enraf Nonius Software V5'
_computing_cell_refinement       'Enraf Nonius Software V5'
_computing_data_reduction        'Corinc (Dr\"ager, 1971)'
_computing_structure_solution    'SIR-97 (Altomare, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_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^)+(0.0934P)^2^+2.2860P] 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     SHELXL
_refine_ls_extinction_coef       0.0022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_number_reflns         1816
_refine_ls_number_parameters     126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.1755
_refine_ls_wR_factor_obs         0.1708
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.3946(5) 0.73255(16) 0.6228(2) 0.0565(8) Uani 1 1 d . . .
H1 H 0.5174 0.7694 0.6024 0.068 Uiso 1 1 d R . .
C2 C 0.1972(6) 0.7466(2) 0.5880(2) 0.0741(11) Uani 1 1 d . . .
H2A H 0.1919 0.7791 0.5535 0.089 Uiso 1 1 d R . .
H2B H 0.1400 0.7035 0.5673 0.089 Uiso 1 1 d R . .
C3 C 0.2361(5) 0.76070(15) 0.68047(18) 0.0500(7) Uani 1 1 d . . .
H3 H 0.1902 0.7344 0.7303 0.060 Uiso 1 1 d R . .
C4 C 0.4455(6) 0.65582(18) 0.6348(2) 0.0593(9) Uani 1 1 d . . .
O5 O 0.3388(4) 0.60759(13) 0.65497(18) 0.0739(8) Uani 1 1 d . . .
O6 O 0.6283(4) 0.64576(13) 0.6202(2) 0.0775(9) Uani 1 1 d . A .
C7 C 0.6920(7) 0.57017(19) 0.6285(3) 0.0900(15) Uani 1 1 d . . .
H7A H 0.6650 0.5514 0.6870 0.108 Uiso 0.55 1 calc PR A 1
H7B H 0.6274 0.5389 0.5858 0.108 Uiso 0.55 1 calc PR A 1
H7A H 0.7406 0.5621 0.6876 0.108 Uiso 0.45 1 calc PR A 2
H7B H 0.5826 0.5373 0.6195 0.108 Uiso 0.45 1 calc PR A 2
C8A C 0.8911(7) 0.57211(19) 0.6130(3) 0.086(3) Uani 0.55 1 d PR A 1
H8A1 H 0.9434 0.5230 0.6181 0.129 Uiso 0.55 1 calc PR A 1
H8A2 H 0.9521 0.6039 0.6553 0.129 Uiso 0.55 1 calc PR A 1
H8A3 H 0.9149 0.5907 0.5548 0.129 Uiso 0.55 1 calc PR A 1
C8B C 0.834(2) 0.5535(7) 0.5693(7) 0.096(4) Uani 0.45 1 d P A 2
H8B1 H 0.8739 0.5030 0.5773 0.145 Uiso 0.45 1 calc PR A 2
H8B2 H 0.9428 0.5857 0.5784 0.145 Uiso 0.45 1 calc PR A 2
H8B3 H 0.7850 0.5600 0.5107 0.145 Uiso 0.45 1 calc PR A 2
C9 C 0.2520(4) 0.83746(14) 0.70795(18) 0.0426(6) Uani 1 1 d . . .
O10 O 0.2974(4) 0.88599(11) 0.66104(14) 0.0585(6) Uani 1 1 d . . .
O11 O 0.2156(3) 0.84482(10) 0.79167(13) 0.0463(5) Uani 1 1 d . . .
C12 C 0.2286(5) 0.91831(16) 0.8255(2) 0.0529(8) Uani 1 1 d . . .
H12A H 0.1311 0.9497 0.7985 0.064 Uiso 1 1 calc R . .
H12B H 0.3554 0.9391 0.8132 0.064 Uiso 1 1 calc R . .
C13 C 0.1972(7) 0.9138(2) 0.9196(2) 0.0729(11) Uani 1 1 d . . .
H13A H 0.2946 0.8828 0.9455 0.109 Uiso 1 1 calc R . .
H13B H 0.0713 0.8932 0.9309 0.109 Uiso 1 1 calc R . .
H13C H 0.2048 0.9625 0.9447 0.109 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
C1 0.085(2) 0.0404(15) 0.0443(14) -0.0005(13) 0.0116(16) 0.0088(15)
C2 0.111(3) 0.0512(17) 0.0604(19) -0.0123(16) -0.027(2) 0.004(2)
C3 0.0635(19) 0.0385(13) 0.0480(15) -0.0070(12) -0.0020(14) -0.0016(14)
C4 0.089(3) 0.0443(17) 0.0443(15) -0.0044(13) 0.0121(16) 0.0113(17)
O5 0.104(2) 0.0419(12) 0.0759(17) -0.0040(11) 0.0082(15) -0.0017(14)
O6 0.098(2) 0.0480(13) 0.0866(18) 0.0136(13) 0.0300(16) 0.0227(13)
C7 0.115(4) 0.053(2) 0.101(3) 0.020(2) 0.038(3) 0.034(2)
C8A 0.058(4) 0.054(4) 0.146(10) 0.021(5) -0.016(6) 0.001(3)
C8B 0.142(13) 0.076(7) 0.072(7) 0.022(5) 0.032(7) 0.039(8)
C9 0.0422(14) 0.0372(13) 0.0483(14) -0.0042(11) -0.0032(12) -0.0012(12)
O10 0.0750(16) 0.0436(11) 0.0570(12) -0.0009(9) 0.0078(11) -0.0032(11)
O11 0.0541(12) 0.0370(9) 0.0479(10) -0.0080(8) -0.0020(9) -0.0012(8)
C12 0.0611(19) 0.0398(13) 0.0578(17) -0.0181(13) -0.0072(15) 0.0043(13)
C13 0.093(3) 0.069(2) 0.0566(19) -0.0235(17) -0.0053(19) 0.003(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
C1 C4 1.471(4) . ?
C1 C2 1.514(6) . ?
C1 C3 1.522(5) . ?
C2 C3 1.485(4) . ?
C3 C9 1.482(4) . ?
C4 O5 1.205(4) . ?
C4 O6 1.320(5) . ?
O6 C7 1.469(4) . ?
C7 C8B 1.392(13) . ?
C7 C8A 1.4231 . ?
C9 O10 1.197(3) . ?
C9 O11 1.332(3) . ?
O11 C12 1.456(3) . ?
C12 C13 1.480(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
C4 C1 C2 115.6(3) . . ?
C4 C1 C3 115.6(3) . . ?
C2 C1 C3 58.6(2) . . ?
C3 C2 C1 61.0(2) . . ?
C9 C3 C2 117.4(3) . . ?
C9 C3 C1 116.1(3) . . ?
C2 C3 C1 60.4(3) . . ?
O5 C4 O6 123.3(3) . . ?
O5 C4 C1 126.2(4) . . ?
O6 C4 C1 110.5(3) . . ?
C4 O6 C7 114.6(3) . . ?
C8B C7 C8A 35.5(6) . . ?
C8B C7 O6 111.8(6) . . ?
C8A C7 O6 105.2(2) . . ?
O10 C9 O11 124.7(2) . . ?
O10 C9 C3 124.0(3) . . ?
O11 C9 C3 111.3(2) . . ?
C9 O11 C12 115.8(2) . . ?
O11 C12 C13 107.1(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
C4 C1 C2 C3 105.6(3) . . . . ?
C1 C2 C3 C9 106.0(3) . . . . ?
C4 C1 C3 C9 146.2(3) . . . . ?
C2 C1 C3 C9 -108.1(3) . . . . ?
C4 C1 C3 C2 -105.6(4) . . . . ?
C2 C1 C4 O5 -33.2(5) . . . . ?
C3 C1 C4 O5 32.5(5) . . . . ?
C2 C1 C4 O6 146.8(3) . . . . ?
C3 C1 C4 O6 -147.5(3) . . . . ?
O5 C4 O6 C7 1.4(5) . . . . ?
C1 C4 O6 C7 -178.6(3) . . . . ?
C4 O6 C7 C8B 144.8(7) . . . . ?
C4 O6 C7 C8A -178.3(2) . . . . ?
C2 C3 C9 O10 -25.5(5) . . . . ?
C1 C3 C9 O10 43.1(4) . . . . ?
C2 C3 C9 O11 156.6(3) . . . . ?
C1 C3 C9 O11 -134.8(3) . . . . ?
O10 C9 O11 C12 1.7(4) . . . . ?
C3 C9 O11 C12 179.6(3) . . . . ?
C9 O11 C12 C13 -176.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        69.89
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.057