A convenient chemo-enzymatic synthesis and 18F-labelling of both enantiomers of trans-1-toluenesulfonyloxymethyl-2-fluoromethyl-cyclopropane
Riss, Patrick Johannes; Rösch, Frank; Organic & Biomolecular Chemistry 6 (2008) 4567–4574; doi:10.1039/b812777h

data_7151030
_publ_section_title
;
 A convenient chemo-enzymatic synthesis and 18F-labelling of both
 enantiomers of
 trans-1-toluenesulfonyloxymethyl-2-fluoromethyl-cyclopropane
;
_journal_issue                   24
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              4567
_journal_page_last               4574
_journal_paper_doi               10.1039/b812777h
_journal_volume                  6
_journal_year                    2008
_chemical_formula_sum            'C9 H14 O4'
_chemical_formula_weight         186.20
_chemical_name_common
'Cyclopropane-1,2-dicarboxylic acid diethyl ester'
_space_group_IT_number           20
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.042(3)
_cell_length_b                   18.432(2)
_cell_length_c                   15.5238(13)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      47
_cell_measurement_theta_min      37
_cell_volume                     2015.0(9)
_computing_cell_refinement       'Enraf Nonius Software V5'
_computing_data_collection       'Enraf Nonius Software V5'
_computing_data_reduction        'Corinc (Dr\"ager, 1971)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare, 1997)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'CAD4 Enraf Nonius'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2091
_diffrn_reflns_theta_full        69.89
_diffrn_reflns_theta_max         69.88
_diffrn_reflns_theta_min         4.80
_diffrn_source                   'rotating anode'
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  0.6835
_exptl_absorpt_correction_T_min  0.6260
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'Corinc (Dr\"ager, 1971)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.51
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(5)
_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_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0641
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0934P)^2^+2.2860P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.1708
_refine_ls_wR_factor_ref         0.1755
_reflns_number_gt                1746
_reflns_number_total             1816
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b812777h.txt
_cod_data_source_block           cpde
_cod_original_cell_volume        2014.9(8)
_cod_database_code               7151030