Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation
Boyd, Derek R.; Sharma, Narain D.; Gunaratne, Nimal; Haughey, Simon A.; Kennedy, Martina A.; Malone, John F.; Allen, Christopher C. R.; Dalton, Howard; Organic & Biomolecular Chemistry 1 (2003) 984–; doi:10.1039/b300867n

data_7150505
_publ_section_title
;
 Dioxygenase-catalysed oxidation of monosubstituted thiophenes:
 sulfoxidation versus dihydrodiol formation
;
_journal_issue                   6
_journal_name_full               'Organic &amp;  Biomolecular Chemistry'
_journal_page_first              984
_journal_paper_doi               10.1039/b300867n
_journal_volume                  1
_journal_year                    2003
_chemical_formula_moiety         'C8 H6 Cl2 O2 S2'
_chemical_formula_sum            'C8 H6 Cl2 O2 S2'
_chemical_formula_weight         269.15
_chemical_melting_point          130.0(10)
_chemical_name_systematic
; 
(+/-)-2,4-dichloro-cis-3a,4,7,7a-tetrahydro-cis-4,7-epithio-
1-benzothiophene-trans-1-syn-8-dioxide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.09(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.283(3)
_cell_length_b                   12.655(4)
_cell_length_c                   9.554(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1001.5(5)
_computing_cell_refinement       'Siemens P3/V2000'
_computing_data_collection       'Siemens P3/V2000'
_computing_data_reduction        'Siemens P3/V2000'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.578
_diffrn_measured_fraction_theta_max 0.578
_diffrn_measurement_device_type  'Siemens P3 diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_av_sigmaI/netI    0.0711
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1409
_diffrn_reflns_theta_full        54.98
_diffrn_reflns_theta_max         54.98
_diffrn_reflns_theta_min         5.80
_diffrn_standards_interval_count 100
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    9.487
_exptl_absorpt_correction_T_max  0.1058
_exptl_absorpt_correction_T_min  0.0657
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.43
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       0.0093(18)
_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   1.056
_refine_ls_hydrogen_treatment    geom
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         724
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0683
_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^)+(0.1296P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1779
_refine_ls_wR_factor_ref         0.1817
_reflns_number_gt                600
_reflns_number_total             724
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b300867n.txt
_cod_data_source_block           7D
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '129-131' was changed to '130.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_cell_volume        1001.4(5)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7150505